Compounds useful for the preparation of various pesticides and their markers

Abstract

In the field of pesticide synthesis, this provides synthetic intermediates, polymorphs and marker compounds, as well as their salts, processes for their preparation, and their uses. [Solution] The present invention provides a variety of compounds that are novel and useful intermediates in a novel method for preparing a specific marker compound, including a specific compound called a saturated target, and its amorphous and crystalline forms, as well as a method for preparing the same, a composition containing the same, a product of the saturated target, and a method for minimizing the content of the storage marker in the composition. In one embodiment, a preservation packaging composition is provided that contains a detectable amount of the compound of formula D, together comprising 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide. JPEG2026090440000659.jpg42161

Description

[Technical Field]

[0001] The present invention relates particularly to the fields of chemistry and agrochemical synthesis. Specifically, the present invention relates to synthetic intermediates, polymorphs and marker compounds, as well as their salts, processes for their preparation and their use. [Background technology]

[0002] International Publication No. 2015 / 084796 and International Publication No. 2016 / 196593 are reported to disclose various substituted cyclic amides, methods for using them as herbicides, and methods for preparing them. International Publication No. 2016 / 094117 discloses specific 3-oxo-3-(arylamino)propanoates, their salts and compositions, processes for preparing them, and their use in preparing specific pyrrolizinones, which are particularly useful as herbicides, among other reported pesticides.

[0003] International Publication No. 2018 / 175226 is reported to disclose specific pyrrolidinenes, intermediates, and methods for preparing them. The inventors also draw attention to the publications International Publication No. 2020 / 242946, International Publication No. 2020 / 064260, U.S. Patent No. 10,676,431, International Publication No. 2019 / 025156, International Publication No. 2018 / 222647, International Publication No. 2018 / 222646, International Publication No. 2018 / 184890, U.S. Patent Application Publication No. 2018 / 099935, European Patent No. 3650430, U.S. Patent Application Publication No. 2018 / 077931, International Publication No. 2016 / 164201, U.S. Patent Application Publication No. 2017 / 158638, and U.S. Patent No. 2020010415. The present inventors further draw attention to International Publication No. 01 / 76566, which teaches the use of amide group-containing polymer compounds or amino group-containing polymer compounds, exemplified by polyvinylpyrrolidone, crosslinked polyvinylpyrrolidone, copolymers of vinylpyrrolidone and vinyl acetate, and polynoxylin, in stabilizing compounds sensitive to acidic environments. [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] The intermediates; markers; compositions; processes for preparing them; and their use in the processes; mixtures; compositions; crystalline forms; and amorphous solid forms of the present invention disclosed herein are not disclosed in these prior publications. Known methods for preparing the chiral compounds mentioned are generally expensive due to the use of expensive starting materials; involve multiple synthesis steps; involve and rely on the use of catalysis using heavy metals such as palladium, rhodium, and iridium; involve ring-closing steps; and suffer from drawbacks including at least one of the following: introducing chirality into the system in the early stages of synthesis, making the selective preparation of the desired syn or anti isomer of compound I difficult. There is a continuous need for alternative processes and novel synthetic intermediates that can mitigate at least some of these problems. Several further novel and non-obvious useful aspects and embodiments of the present invention are direct results of the processes and novel synthetic intermediates of the present invention disclosed herein. [Means for solving the problem]

[0005] This invention relates to a specific compound called a saturated target, its amorphous and crystalline forms, and various compounds that are novel and useful intermediates in a novel method for preparing a specific marker compound, including a conserved marker compound, as well as methods for preparing them, their use, and the product of the saturated target. The present invention relates to compositions including the same, and to methods for minimizing the content of preservation markers in the composition. [Brief explanation of the drawing]

[0006] [Figure 1] Tetoflupyrrolimethform I-DSC [Figure 2] Tetoflupyrrolimethform II-DSC [Figure 3] Tetoflupyrrolimethform I-TGA [Figure 4] Tetoflupyrrolimethform II-TGA [Figure 5] Tetoflupyrrolimethform I-XRD [Figure 6]Tetoflupyrrolimethform II-XRD [Figure 7] Tetoflupyrrolimeth morph I and morph II - XRD overlay [Figure 8] Tetoflupyrrolimeth 9:1 mixture Form I and Form II-XRD [Figure 9] Tetoflupyrrolimeth morphological I IR spectrum [Figure 10] Tetoflupyrrolimeth morphology II IR spectrum [Figure 11] Tetoflupyrrolimeth morphology I and morphology II-IR overlay spectra [Figure 12] Preservation marker - LC / MS - Preservation marker for tetoflupyrrolimeth, molecular weight 286 [Figure 13] Tetoflupyrrolimeth + Preservation Marker - LC / MS [Figure 14] Storage marker molecular weight 286-LC / MS [Modes for carrying out the invention]

[0007] definition Before describing this subject matter in detail, it may be useful to provide definitions of the specific terms used herein. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those generally understood by those skilled in the art to which this subject matter belongs.

[0008] As used herein, the terms “one (a)” or “one (an)” include both singular and plural forms unless otherwise specified. Therefore, the terms “one (a),” “one (an),” or “at least one” are interchangeable in this application.

[0009] Furthermore, unless explicitly stated otherwise, "or" refers to an inclusive or not exclusive or. For example, condition A or B is satisfied by one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0010] Throughout this application, the description of various embodiments uses the term "including," but it will be understood by those skilled in the art that in some specific examples, embodiments may be described using alternative terms such as "containing," "essentially consisting of," or "consisting of."

[0011] For a better understanding of this instruction, and without limiting its scope, unless otherwise indicated, all numbers representing quantities, percentages, or proportions, as well as other numerical values ​​used in the specification and claims, should be understood in all cases to be modified by the term "about."

[0012] Therefore, unless otherwise indicated, the numerical parameters described in the following specification and the attached claims are approximations that may vary depending on the desired characteristics to be obtained. At a minimum, each numerical parameter is rounded using the usual rounding technique in light of the number of significant figures reported. It should be interpreted at least by applying the technique. In this regard, the use of the term “about” in this specification particularly includes + / - 10% of the indicated value within the range unless otherwise specified. Furthermore, all endpoints of all ranges that cover the same component or characteristic in this specification include the endpoints, can be combined independently, and include all intermediate points and ranges.

[0013] In this invention, the following terms and conditions have the following meanings.

[0014] All figures and references herein relating to saturated target compounds, unsaturated precursor compounds, Compound III, Compound IV, or storage marker compounds are, unless otherwise specifically defined, or unless the context in which they are referred to is clearly limited to a particular structure, or unless their inclusion introduces unpatentable subject matter or scope, to be reasonably understood by those skilled in the art, including their analogues, isomers, salts, N-oxides, esters, etc., and having the intended or resulting functions and utility of the compounds referred to.

[0015] Saturated targets, unsaturated precursors, compound III, compound IV, and conservation markers may be referred to multiple times, for example, as saturated targets, unsaturated precursors, compound III, compound IV, and conservation markers, to reflect multiple compounds encompassed by the general structures describing them. However, this should not be attributed to any significance, and no inferences should be made when singular terms are used for textual convenience.

[0016] Where necessary, the disclosed structure of a particular compound is labeled with a number to facilitate a clearer identification of the compound.

[0017] In many cases, and where appropriate, specific structures disclosed are further labeled with letters and numbers to facilitate comparison with general synthesis schemes disclosed herein.

[0018] Using saturated target compounds and some of the intermediates of the present invention that can generate them, unsaturated precursors, Compound III and Compound IV, and the preparation methods of the present invention described herein, the conserved marker compounds may exist as isomers, in particular as one or more stereoisomers. Various stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. For example, saturated targets are understood to be chiral. If only one structure is depicted or labeled as "1" or described as a saturated target, companion enantiomers, diastereomers, or optical isomers of the saturated target, including both 1 or its optically active mixtures and racemic mixtures, etc., should not be inferred from the omission of the corresponding structure of the partner compound unless specifically stated or evident from the context in which the structure appears. Similarly, examples of the intermediate compounds and marker compounds of the present invention, unsaturated precursors, Compound III and Compound IV, and the conserved markers and corresponding saturated targets are isomers, including, for example, cis-trans and / or EZ isomers. Where only one isomer structure is depicted or labeled, all companion isomers are explicitly intended to be as is evident to those skilled in the art, that they have similar functions / properties, and should not be inferred from the omission of the corresponding structure for the convenience of texture unless otherwise specified or evident from the context in which the structure appears.

[0019] It is generally understood that the crystalline form of a compound cannot be fully characterized by a single peak in the powder X-ray diffraction pattern. However, with regard to distinguishing only the two known crystalline forms of tetoflupyrrolimeth described herein, it should be noted that each powder X-ray diffraction pattern shows at least one peak that is absent or below detection level in the powder X-ray diffraction patterns of the other polymorphic form. Therefore, if the crystalline form has already been chemically identified as tetoflupyrrolimeth, as disclosed herein, The two novel polymorphs can be distinguished by this single characteristic peak. Therefore, the inventors refer to this type of peak as a differential peak. Clearly, each differential peak is also part of each of the list of characteristic peaks.

[0020] In the definition of the disclosed structures, the term “carbonyl” is intended to include the corresponding “carbonyl” protected as an acetal of a C1-C8 alcohol, e.g., ethanol, or a C1-C8 diol, e.g., ethylene glycol, 1,3-propanediol, or propylene glycol. As an example, the term “dimethylcarbonyl” would include the corresponding acetal exemplified by MeC(OCH2CH2O)Me.

[0021] In this specification, the term “metal” is intended to include all forms of metals, including but not limited to metal salts and metal complexes.

[0022] In embodiments of the synthesis process of the present invention disclosed herein, where the use of a Grignard reagent is indicated, a Grignard reagent that is not aliphatic, such as an alkyl-type Grignard reagent, is particularly preferred.

[0023] Furthermore, in embodiments of the synthesis process of the present invention disclosed herein, where the use of a Grignard reagent is indicated, it will be apparent to those skilled in the art of these preparation techniques that a similar organometallic compound or alternative nucleophile can be substituted for the Grignard reagent. Preferred examples of these alternative nucleophiles are organolithium compounds. These explicitly include organocopper and organozinc compounds, such as phenyl(3-(trifluoromethyl)phenyl)zinc, 3-(trifluoromethyl)phenyl)lithium, bis(3-(trifluoromethyl)phenyl)zinc(II) bromide, bis(3-(trifluoromethyl)phenyl)cuprate(I), bis(3-(trifluoromethyl)phenyl)copper, etc., and combinations of these types of reagents.

[0024] In embodiments of the synthesis process of the present invention disclosed herein, where the use of a nucleophile, such as a Grignard reagent, is indicated, the use of a hydrogen / hydride source or hydrogenation is also intended as an option included within the concept of using a nucleophile, as exemplified by the use of electron sources such as H2 / Pd, NaBH4, CuH, or H2 / Raney Ni, and Zn / AcOH, Na / NH3.

[0025] The term Grignard reagents include organomagnesium compounds in which Mg is bonded to a carbon atom containing an Ate complex, such as iPrMgCl and MeMgCl2Li, as well as turboGrignards.

[0026] In general structures representing groups of compounds, unless otherwise specified, each example of a substituent can be selected independently of any of the definitions of that substituent. For example, a compound within a group represented by CH(R')3, where R' is defined as F, Cl, or I, may include the compound CH(F)(Cl)(I).

[0027] The present invention relates, in particular, to each of the compounds of formulas 2, 3, and 4 as defined below, which are referred to herein as unsaturated precursors, as well as to intermediates III and IV. [ka] As further defined below, this is a novel and useful intermediate in novel preparation methods for certain pesticide compounds, particularly those identified herein as compounds of Formula 1 and commonly referred to as saturated targets, pyrrolidinone (as defined below). An example of these methods is shown in the following scheme. [ka]

[0028] However, each unsaturated precursor; compound III; IV is useful individually as an intermediate for the preparation of the saturated target, independently of the others in the series of reactions exemplified. Advantageously, the saturated target is pyrrolizinone, the anilide insecticide most exemplified by 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide. [ka] Most specifically, optical isomers and / or diastereomers useful as herbicides, comprising the following structures, [ka] Includes.

[0029] The present invention also relates to the following formula D [ka] With regard to certain marker compounds, including those identified herein as storage markers, as exemplified by the compounds, This is the following structure [ka] Further generated from the exemplary saturated target compound having the following scheme, [ka] In this invention, the conversion rate, degree of conversion, and amount of the generated storage marker of formula D, exemplified by (3S,4S)-2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide, as well as its content in a mixture with the saturated target compound composition from which it was generated, are mediated by the properties of the composition and its storage history under various defined environmental conditions, particularly exposure to sunlight. Thus, the storage marker of formula D is novelly utilized as a marker indicating evidence of the properties of the composition and past storage conditions.

[0030] Accordingly, the present invention also relates to a method for preparing saturated target compounds, as well as a method for preparing each of the various individual intermediates referred to herein as unsaturated precursors and compound III, which are the subject of embodiments of the present invention, and IV of formula D and the conserved marker compound, and in particular an industrially useful method for the efficient preparation of certain pyrrolizinones, which are anilide insecticides, as exemplified by the optically active compound 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide from the aforementioned intermediate compounds.

[0031] The present invention also relates to novel mixtures and compositions comprising saturated target and storage marker compounds, exemplified by mixtures of anilide pestiside and the respective markers described above, which exhibit or are evidence of suboptimal storage conditions and / or unfavorable compositional properties or components of the mixture.

[0032] The present invention further relates to methods, components, and packaging useful for minimizing the content of the preservation marker compound in a saturated target composition, particularly by minimizing, avoiding, or mitigating the effects of exposure of the composition to sunlight.

[0033] The present invention is clearly and closely related to novel physical / chemical properties and / or attributes of saturated target compounds resulting from processes utilizing the unsaturated precursors and compounds III and IV of the present invention as intermediates in their preparation.

[0034] Therefore, chemically, a saturated target compound; compound III; or IV prepared as an intermediate using any of the unsaturated precursors may have a novel impurity profile, containing at least trace amounts of either unsaturated intermediate; III; or IV as impurities carried over from the process, thus providing novel evidence that the saturated target compound was prepared using any of the compounds, unsaturated intermediates, III, or IV of the present invention as an intermediate. The combination of the saturated target with either unsaturated precursor III or IV is novel in itself and has utility, among other things, in the analysis of test saturated targets for determining their preparation pathway and in other uses unrelated to being a preparation intermediate.

[0035] As described above, saturated target compounds produced by processes utilizing the unsaturated precursors, compounds referred to as III and IV of the present invention, as intermediates in their preparation, also consequently possess novel physical properties and / or attributes. In one non-limiting example, these features include, but are not limited to, When produced by the method and intermediates of the present invention, novel and useful polymorphs of 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide and its individual enantiomers / diastereomers, and It contains a mixture of these.

[0036] Accordingly, the present invention also relates to each of the crystalline polymorphs of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (tetoflupyrrolimeth) in both amorphous and noncrystalline solid forms, as well as in the noncrystalline form, a carrier, or additional components, etc. All of these mixtures are included in the term "composition" herein. Therefore, generally, the term "composition" herein should be understood to include all mixtures of two or more materials, including mixtures of active ingredients, intermediates, and markers, even if they do not contain inert or inert components or carrier materials.

[0037] It is well understood that compounds with different crystalline polymorphic forms can typically exhibit different physical properties across a wide range of parameters, depending on the polymorph, with respect to solubilization rate, fluidity, stability, compressibility, or even reflectivity. Considering a large array of pesticide compositions, particularly herbicidal compositions, each has its own unique requirements. Having alternative, novel, and useful polymorphs of agricultural active ingredients that enable formulation in a wider range of delivery forms is advantageous in itself. In particular, it is useful in enabling a wider range of formulation techniques. Similar advantages are often obtained by producing amorphous or non-crystalline forms, for example, because they generally have a faster dissolution rate. Spray drying, freeze-drying, solid solutions, and adsorption to carrier substrates are some typical methods for obtaining such solid forms, but the stability of the susceptible compound must be considered.

[0038] Specifically, the present invention includes a novel tetoflupyrrolimeth polymorph I exhibiting at least one of the following characteristics: The infrared spectrum is essentially shown in Figure 9. The powder X-ray diffraction pattern is essentially as shown in Figure 5. Powder X-ray diffraction pattern with a differential peak at 9.6 at 2θ(±0.20), A powder X-ray diffraction pattern having at least four characteristic peaks represented by 2θ(±0.20) at 9.6, 15.0, 17.3, 17.9, 21.6, and 24.6.

[0039] Specifically, the present invention includes a novel tetoflupyrrolimeth polymorph II exhibiting at least one of the following characteristics: The infrared (IR) absorption spectrum is essentially shown in Figure 10. An infrared (IR) absorption spectrum having at least one characteristic peak selected from values ​​expressed as cm⁻¹ (±1 cm⁻¹) at 1678, 1546, 1395, 946, 924, 885, 825, and 662. The powder X-ray diffraction pattern is essentially as shown in Figure 6. Powder X-ray diffraction pattern having a differential peak represented by 2θ(±0.20) at 6.9, The following: Powder X-ray diffraction pattern having at least four characteristic peaks, represented by 2θ(±0.20) selected from the values ​​of 6.9, 11.2, 17.7, 23.5, and 26.3.

[0040] The present invention further relates to a process for preparing crystalline polymorphs I and II of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (tetoflupyrrolimeth) as described in the present invention.

[0041] Embodiments and Description Unsaturated precursors III and IV as defined below and in the following embodiments, respectively The compounds of formulas 2, 3, and 4, referred to as such, can each be prepared individually by general methods known to those skilled in the art in the field of synthetic organic chemistry. [ka]

[0042] The compound, the unsaturated precursor, and each of III and IV are, a. Novel compounds not previously disclosed for chemical, biological, or agricultural purposes; b. Novel synthetic intermediates that have not been previously disclosed as being useful in the preparation of corresponding saturated target compounds; c. Novel combination partners with saturated target compounds that remain as synthetic impurities after use as synthetic intermediates in the preparation of the saturated target; and d. At least one, preferably all, of the marker compounds that serve as evidence of the use of a novel method for preparing a tested sample of the saturated target substance.

[0043] In one embodiment, the method of the present invention for preparing a saturated target compound may include a scheme utilizing all of the compound, the unsaturated precursor, III and IV, and also clearly include individual embodiments of the method for preparing each intermediate compound without referring to its subsequent use as an intermediate in a multi-step preparation. [ka]

[0044] However, the process of the present invention for preparing saturated target compounds involves the use of only one and / or two of the three corresponding novel intermediate compounds, and the absence of the others, which is entirely within the scope of the invention and specifically intended by the inventors. Therefore, it is useful to consider each of the claimed compounds as inventively independent of one another.

[0045] The inventors have specifically contemplated a process for preparing a saturated target of Formula 1 directly from the corresponding intermediate compound of Formula 3 or Saturated Target of Formula 4, without the involvement of any other disclosed intermediate compounds and / or via any other unclaimed intermediates. Examples include the process of the following general scheme, the details of which will become immediately apparent to those skilled in the art of these synthetic chemical techniques after the materials disclosed herein. [ka]

[0046] Similarly, in some cases, the unsaturated precursor of formula 2 may be prepared directly from some compound IV of formula 4. [ka]

[0047] Therefore, each of the compounds, the unsaturated precursor, III, and IV is individually useful as an intermediate for the preparation of the saturated target, without depending on the others in the reaction chain illustrated above.

[0048] Known methods for preparing saturated targets of formula 1 are generally expensive because they use expensive starting materials, involve multiple synthesis steps, include the use of heavy metals such as palladium, rhodium, and iridium, and / or involve closing the ring-labeled P in the following structures based on catalytic interaction with heavy metals, and / or introduce chirality into the system in the early stages of synthesis, making it difficult to selectively prepare the desired syn or anti isomer of the compound of formula 1. [ka]

[0049] Accordingly, in one embodiment, the present invention provides a novel intermediate compound that can be used in a novel method for synthesizing a saturated target of formula 1 via a reaction at a cyclic double bond in the cyclic system of an unsaturated precursor of formula 2, the step of which does not require the same expensive catalysts, such as Pd, Rh, or Ir, as required in previous processes. [ka]

[0050] The present invention also teaches and provides inexpensive ring-closing starting materials and intermediates that can be used in the synthesis of unsaturated precursors, thereby avoiding the need for ring-closing synthesis steps as illustrated in the following scheme. [ka]

[0051] This embodiment can be illustrated by the following scheme, which uses the inexpensive and readily available solvent N-methylpyrrolidone (NMP) as a starting material. [ka]

[0052] Notably, lactams / secondary amides with the following structures [ka] The reaction with Grignard reagents or organolithium reagents results in 1,4 addition instead of simple deprotonation and deactivation of lactam / secondary amides, or other undesirable reactions such as attack on the amide.

[0053] The synthetic preparative method of the present invention enables a process that does not require expensive metals such as Pd, Rh, Pt, and Ir, and the use of relatively inexpensive and readily available Grignard reagents or organolithium reagents can also advantageously generate several marker compounds useful for demonstrating the use of the method of the present invention, although not all or any of the markers are always generated.

[0054] For example, in the following scheme, [ka] The markers that can be formed using the above scheme may include some of the following structures. [ka] Another example can be seen in the following scheme. [ka] The markers that can be formed in this scheme may include some of the following structures. [ka]

[0055] As mentioned above, the use of this type of Grignard reagent and / or organolithium reagent can be highly desirable for industrial-scale manufacturing, reducing and / or eliminating waste problems, such as those involving heavy metals, B, etc., avoiding the use of expensive metals, such as Rh, Pd, Ir, Pt, etc., reducing the number of synthesis steps, and eliminating the need to purify the desired saturated target product from problematic residual impurities.

[0056] The use of the intermediates and processes of the present invention disclosed herein may also be accompanied by some or all of the following potential advantages: Improved syn-anti selectivity and introduction of chirality in the later stages of synthesis reduce the risk of partial or even complete racemization in the final saturated target product, thus improving the yield of the desired chiral compound and thus reducing production costs.

[0057] The disclosed process also reduces the number of synthetic steps required for the preparation of saturated target products, enables synthesis starting from cyclic compounds, and thus avoids the need for cyclization as part of the synthesis.

[0058] The starting materials may also be significantly cheaper than those previously disclosed, the process requires less expensive reagents and catalysts, and eliminates the need for expensive heavy metals such as palladium and ruthenium.

[0059] Some more detailed exemplary process methods disclosed below may be useful for understanding some aspects and embodiments of the present invention. In order to limit the scope of the present invention as conceived by the inventors, none of the process details described below herein should ever be considered. Conversely, the individual steps and process details in the following examples should not be considered only as part of a particular complete synthesis scheme, and other steps are not necessarily taught herein, each of which can be viewed as an individual step with its own value.

[0060] As will be immediately apparent to those skilled in the art, the methods disclosed below are not necessarily preferred methods and are intended to provide some color, range, depth, and breadth to a more general description.

[0061] Embodiments of the present invention include the following:

[0062] Embodiment A1 Unsaturated precursors of formula 2 and, for example, their salts. [ka] (In the formula, R α This includes halogens; carbon-containing groups exemplified by substituted or unsubstituted alkyl, aryl, heterocyclic, and naphthyl groups; esters including aliphatic and aromatic esters exemplified by C(O)OC6H5 and -C(O)OC6H4F; amides including aliphatic and aromatic amides exemplified by -C(O)NHC6H5; hydrazine amides, such as -C(O)NHNHC6H5, thioesters, thionoesters, and -C(O)NHOC6F5; and aliphatic and aromatic hydrazine amides exemplified by similar compounds such as -C(S)SC6H5, however, R α Since it is not bonded to the ring via O or N, for example, R α It cannot be -OMe.

[0063] R β This refers to hydrogen or carbon-containing groups, exemplified by substituted or unsubstituted alkyl, aryl, naphthyl, heterocyclic, etc., bonded to a ring via a C atom or, where applicable, a Si atom. However, R β It cannot be an amine bonded to the ring via N. R β It does not need to be ether-bonded to the ring via O. R β It is not a thioether bonded to the ring via S, A αis a C, N, O or S atom, with or without substitution, exemplified by -N(Me)-; -O-.

[0064] When present, the substituent of A α may be attached to another part of the molecule such as Q α , A β etc.

Chemical Structure

[0065] Each A β is, independently of each other, a C, N, O or S atom, with or without substitution, exemplified by -CH2- or -O-.

[0066] When present, the substituent of each A β may be attached to another part of the molecule such as A α , A β , R β etc., provided that at least one of A β is a saturated atom exemplified by CH2. nα is 1, 2 or 3. Each Q α is, independently of each other, O, S or NR ε . R ε is a C, N, O or S atom with or without substitution exemplified by -N(Me)2.

[0067] R ε The substituent on R may be hydrogen or a carbon- and / or nitrogen-containing group, for example, substituted or unsubstituted alkyl, aryl, naphthyl, poly

[0068] When present, the substituent of R ε may be, for example, in the following structure, Q within the ring via a C atom or, in relevant cases, a Si atom α , A βIt may also be bonded to another part of the molecule. [ka]

[0069] In general, the ring portion of the unsaturated precursor labeled with P below is not aromatic; that is, not all atoms can be conjugated. Furthermore, the double bond in that ring portion, as shown below, is also not part of the outer aromatic addition ring. [ka]

[0070] Embodiment A2 Unsaturated precursors of formula 2 and, for example, salts thereof, [ka] Unsaturated precursors do not contain covalent nitrogen-halogen bonds. R α Halogen (Hal.), C1~C 10 Alkyl, C1-C 10 Haloalkyl, R μ or -C(Q α )Q β R μ That is the case. In some situations, R α Also, another part of the molecule, for example, Q within the ring α , A β They may be connected to each other, Q β O, S, NR ε , NR π -NR π , NR π -O, NR π -S, S-NR π , or O-NR π And, R β H, R ε , or Si(R ε )3, A αis a C, N, O, or S atom having 0 to 2 substituents. The substituents, if present, are H and / or R as defined below. θ You can choose from A α Examples include -N(Me)-, -C(Et)H-, and -O-.

[0071] In some situations, A α The substituents are, for example, Q α , A β It may also be bonded as a ring to another part of the molecule, such as: [ka] Each A β These are, individually and independently, C, N, O, or S atoms having 0 to 2 substituents. For example, A β These can be -N(Me)-, -C(Et)H-, -O-, etc. Each A β The substituents above are Ring A β Provided that at least one of the atoms is a saturated atom as exemplified by CH2, H and / or R are defined below. θ Selected from. Furthermore, in some situations, each A β Q α , A α Another part of the molecule or another A β They may be bonded to each other to form a ring. nα is between 1 and 3.

[0072] Q α O, S, NR ε And in certain situations, A within the ring β It may also be bonded to another part of the molecule.

[0073] Each R θThese are, individually and independently, halogen (Hal.), hydroxy (OH), cyano (CN), nitro, amino, C1-C8 alkyl, C1-C8 cyanoalkyl, C1-C8 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 hydroxyalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C4-C 10 Cycloalkylalkyl, C4~C 10 Halocycloalkylalkyl, C5~C 12 Alkylcycloalkylalkyl, C5~C 12 Cycloalkyl alkenyl, C5~C 12 Cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C 10 Alkylcycloalkyl, C6~C 12 Cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyalkoxy, C4-C 10 Cycloalkoxyalkyl, C3-C 10 Alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C 10 Cycloalkylaminoalkyl, C3~C 10 Dialkylaminoalkyl, -CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, -C(=O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10Cycloalkoxycarbonyl, C5 - C 12 Cycloalkylalkoxycarbonyl, -C(=O)NH2, C2 - C8 alkylaminocarbonyl, C4 - C 10 Cycloalkylaminocarbonyl, C3 - C 10 Dialkylaminocarbonyl, C1 - C8 alkoxy, C1 - C8 haloalkoxy, C2 - C8 alkoxyalkoxy, C2 - C8 alkenyloxy, C2 - C8 haloalkenyloxy, C3 - C8 alkynyloxy, C3 - C8 haloalkynyloxy, C3 - C8 cycloalkoxy, C3 - C8 halocycloalkoxy, C4 - C 10 Cycloalkylalkoxy, C3 - C 10 Alkylcarbonylalkoxy, C2 - C8 alkylcarbonyloxy, C2 - C8 haloalkylcarbonyloxy, C4 - C 10 Cycloalkylcarbonyloxy, C1 - C8 alkylsulfonyloxy, C1 - C8 haloalkylsulfonyloxy, C1 - C8 alkylthio, C1 - C8 haloalkylthio, C3 - C8 cycloalkylthio, C1 - C8 alkylsulfinyl, C1 - C8 haloalkylsulfinyl, C1 - C8 alkylsulfonyl, C1 - C8 haloalkylsulfonyl, C3 - C8 cycloalkylsulfonyl, formylamino, C2 - C8 alkylcarbonylamino, C2 - C8 haloalkylcarbonylamino, C3 - C8 cycloalkylamino, C2 - C8 alkoxycarbonylamino, C1 - C6 alkylsulfonylamino, C1 - C6 haloalkylsulfonylamino, -SF5, -SCN, SO2NH2, C3 - C 12 Trialkylsilyl, C4 - C 12 Tr Trialkylsilylalkyl, C4 - C 12 Trialkylsilylalkoxy, R σ 、R η S(=O)=N -, R η S(=O)2N, R η -C(=O)-, R η (R η N=) q S(=O) p-Cyano, formyl, C3-C8 alkylcarbonylalkyl, -C(C1-C4 alkyl), N-O(C1-C4 alkyl), -C(O)NH2, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C4-C8 cycloalkenyl, arylcarbonyl, arylalkenylalkyl, arylcarbonylalkyl or -CPhisN-O(C1-C4 alkyl), each of which is optionally substituted on the ring members having up to 5 substituents independently selected from R η and is optionally substituted on the ring members having up to 5 substituents independently selected therefrom.

[0074] R θ In the situation where R is attached to another part of the molecule, the bond is through a saturated, partially unsaturated or fully unsaturated chain containing 2-4 atoms selected from up to 4 C atoms, up to 1 O atom, up to 1 S atom and up to 2 N atoms, up to 2 carbon members of the chain being independently selected from C(=O) and C(=S), and the sulfur atom member of the chain being S(-O) u (-NR ζ ) v selected from, and the chain being optionally substituted with up to 5 substituents independently selected from R substituted on carbon atoms and / or nitrogen atoms η and R λ is H or R μ and R λ may be attached to another part of the molecule such as Q α , A β etc.

[0075] R μ is a phenyl ring or a naphthalenyl ring system, each ring or ring system being substituted or unsubstituted with up to 5 substituents independently selected from R or a 4-7 member heterocyclic ring; or an 8-10 member bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from up to 2 O atoms, up to 2 S atoms, and up to 5 N atoms, up to 3 C ring members being independently selected from C(=O) and C(=S), and sulfur atom ring members being independently S(=O) ζ; (=NR u (=NR ζ )v Selected from, each ring or ring system is R of carbon atom ring members ζ Independently selected from, the nitrogen atom ring member R η It is substituted or unsubstituted with up to 5 substituents selected from the following: R π is H or R θ That is the case. R ε These are R, respectively. π A C, N, O, or S atom having 0 to 2 substituents selected from the following: -N(Me)2 is an example. The substituents are, Q within the ring α , A β They may be further bonded to other parts of molecules such as these.

[0076] Each R ζ These are individually and independently: Hal, OH, CN, nitro, amino, C1-C8 alkyl, C1-C8 cyanoalkyl, C1-C8 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 hydroxyalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C4-C 10 Cycloalkylalkyl, C4~C 10 Halocycloalkylalkyl, C5~C 12 Alkylcycloalkylalkyl, C5~C 12 Cycloalkylalkenyl, C5~C 12 Cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C 10 Alkylcycloalkyl, C6~C 12 Cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyalkoxy, C4-C 10Cycloalkoxyalkyl, C3-C 10 Alkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C 10 Cycloalkylaminoalkyl, C3~C 10 Gia Cylaminoalkyl, -CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, -C(=O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, -C(=O)NH2, C2~C8 alkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C3~C 10 Dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C 10 Cycloalkylalkoxy, C3-C 10 Alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C 10Cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C3-C8 cycloalkylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, -SF5, -SCN, SO2NH2, C3-C 12 Trialkylsilyl, C4~C 12 Trialkylsilylalkyl, C4~C 12 Trialkylsilylalkoxy, R η , R η S(=O)=N-, R η S(=O)2NR η -C(=O)- or R η (R η N=) q S(=O) p - and the free bond protruding to the right is, for example, R μ It shows the connection point to, Depending on the situation, R ζ Q α , A β They may be linked to other parts of molecules such as the above to form a ring.

[0077] Each R η These are, individually and independently, CN, C1-C3 alkyl, C1-C8 hydroxyalkyl, and C2-C3 alkenyl. C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl These are C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl, or C3-C4 dialkylaminoalkyl.

[0078] R ηIt may also be bonded to other parts of the ring-forming molecule, such as Qα, Aβ, etc.

[0079] Each R σ These are, individually and independently, phenyl, phenylmethyl (benzyl), pyridinylmethyl, phenylcarbonyl (i.e., benzoyl), phenoxy, phenylethynyl, phenylsulfonyl, or a heterocyclic ring of 5 or 6 members, each being R λ A ring member having up to 5 substituents independently selected from, which is either substituted or unsubstituted, q is between 0 and 4. p is between 0 and 4. u is between 0 and 4. v is between 0 and 4.

[0080] Embodiment A2a Unsaturated precursor and, for example, salt thereof of Embodiment A2 (wherein nα is 1, R α , R β Q α Q β , A β , A α and R μ (This has the same meaning as defined in Embodiment A2).

[0081] Embodiment A2b Unsaturated precursor and, for example, salt thereof of Embodiment A2 (wherein nα is 2, R α , R β Q α Q β , A β , A α and R μ (This has the same meaning as defined in Embodiment A2).

[0082] Embodiment A2c Unsaturated precursor and, for example, salt thereof (wherein R is used in the formula) of Embodiment A2 βは , H, R α Q α Q β , Aβ , A α , R μ (and nα have the same meaning as defined in Embodiment A2).

[0083] Embodiment A2d Unsaturated precursor and, for example, salt thereof (wherein R is used in the formula) of Embodiment A2 α , R β Q α Q β , A β , A α , R μ And nα have the same meaning as defined in Embodiment A2, except R β (It is not H).

[0084] Embodiment A3 One unsaturated precursor of Embodiments A2; A2a; A2b; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(Q α )Q β R μ , [ka] R β Q α Q β , A β , A α , R μ (and nα have the same meaning as defined in Embodiment A2).

[0085] Embodiment A4 One unsaturated precursor of Embodiments A2; A2a; A2b; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- [ka] Rβ Q α Q β , A β , R π , R μ (and nα have the same meaning as defined in Embodiment A2).

[0086] Embodiment A5 One unsaturated precursor from Embodiments A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 1, [ka] R β Q α Q β , A β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0087] Embodiment A6 One unsaturated precursor from Embodiments A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 1, A β CH2, [ka] And in the formula, R β Q α Q β , R π and R μ(This has the same meaning as defined in Embodiment A2).

[0088] Embodiment A7 One unsaturated precursor from Embodiments A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 2, A β CH2, [ka] And R β Q α Q β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0089] Embodiment A8 One unsaturated precursor from Embodiments A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(O)Q β R μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O, [ka] And R β Q β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0090] Embodiment A9 One unsaturated precursor from Embodiments A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH, [ka] And R β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0091] Embodiment A10 One unsaturated precursor from Embodiments A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α is O, Q β NH is, R μ is either non-substitutive or R ζ [ka] A phenyl ring substituted with up to 5 substituents independently selected from, R β , R π and R ζThis has the same meaning as defined in Embodiment A2.

[0092] Embodiment A11 An unsaturated precursor of Embodiment A2, and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β is either non-substitutive or R ζ [ka] (In the formula, R π and R ζ R is a phenyl ring substituted with up to five substituents independently selected from (which have the same meaning as defined in Embodiment A2). λ (That is.)

[0093] Embodiment A12 An unsaturated precursor of Embodiment A2, and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μis either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β is either non-substitutive or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from λ And, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0094] Embodiment A13 An unsaturated precursor of Embodiment A2, and, for example, a salt thereof (in the formula, unsaturated precursor R α is -C(O)NHR μ And, A α It is -NH-, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β is either non-substitutive or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from λ And, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0095] Embodiment A14 An unsaturated precursor of Embodiment A2, and, for example, a salt thereof (in the formula, Rα is -C(O)NHR μ And, A α It is -NH-, nα is 2, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β is either non-substitutive or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from λ And, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0096] Embodiment A15 An unsaturated precursor of Embodiment A2, and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 2, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β is either non-substitutive or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from λ And, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0097] Embodiment A16 An unsaturated precursor having the following structure, [ka]

[0098] Embodiment A16a A pesticide synthesis intermediate compound having the following structure, [ka]

[0099] Embodiment A17 An unsaturated precursor having the following structure, [ka]

[0100] Embodiment A17a A pesticide synthesis intermediate compound having the following structure, [ka]

[0101] Embodiment A18 An unsaturated precursor having the following structure, [ka]

[0102] Embodiment A19 An unsaturated precursor having the following structure, [ka]

[0103] Embodiment A20 An unsaturated precursor having the following structure, [ka]

[0104] Embodiment A21 An unsaturated precursor having the following structure, [ka]

[0105] Embodiment A22 An unsaturated precursor having the following structure, [ka]

[0106] Embodiment A23 An unsaturated precursor having the following structure, [ka]

[0107] Embodiment A24 An unsaturated precursor having the following structure, [ka]

[0108] Embodiment A25 An unsaturated precursor having the following structure, [ka]

[0109] Embodiment A26 An unsaturated precursor having the following structure, [ka]

[0110] Embodiment A27 An unsaturated precursor having the following structure, [ka]

[0111] Embodiment A28 An unsaturated precursor having the following structure, [ka]

[0112] Embodiment A29 An unsaturated precursor having the following structure, [ka]

[0113] Embodiment A30 An unsaturated precursor having the following structure, [ka]

[0114] Embodiment A31 Unsaturated precursors and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β H is H, [ka] R π and R ζ (This has the same meaning as defined in Embodiment A2).

[0115] Embodiment A32 Unsaturated precursors and, for example, salts thereof of Embodiment A2 (wherein, R α is -C(O)NHR μ And, A α It is -NH, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β H is H, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0116] Embodiment A33 Unsaturated precursors and, for example, salts thereof of Embodiment A2 (wherein, R α is -C(O)NHR μ And, A α It is -NH, nα is 2, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζA phenyl ring substituted with up to 5 substituents independently selected from, R β H is H, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0117] Embodiment A34 Unsaturated precursors and, for example, salts thereof of Embodiment A2 (wherein, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 2, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β H is H, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0118] Embodiment A35a An unsaturated precursor defined by one of the following structures, [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 3 , R 4 , R 6(Y1 and Y2, etc., have the meanings defined in claim 1 of PCT / US2014 / 068073, which was published as International Publication Brochure No. 2015 / 084796). The text extracted from claim 1 from page 286, line 6 to page 289, line 23 of International Publication Brochure No. 2015 / 084796 is incorporated by reference specifically for the purpose of defining the structure of this embodiment.

[0119] Q 1 This is a phenyl ring or naphthalenyl ring system, and each ring or ring system is R 7 It is optionally substituted with up to five substituents independently selected from or is a heteroaromatic bicyclic ring system of 5-6 membered rings or 8-10 membered rings, each ring or ring system containing a carbon atom and 1-4 heteroatoms independently selected from up to 2 oxygen atoms, up to 2 sulfur atoms, and up to 4 nitrogen atoms, the up to 3 carbon ring members being independently selected from C(=O) and C(=S), and the sulfur ring member being S(=O) u (=NR 8 ) v Independently selected from, each ring or ring system has R on the carbon atom ring member. 7 R on the nitrogen atom ring member is selected independently from 9 It is optionally substituted with up to 5 substituents selected from the following: Q 2 This is a phenyl ring or naphthalenyl ring system, and each ring or ring system is R 10 It is optionally substituted with up to five substituents independently selected from; or it is a 5-6 member fully unsaturated heterocyclic ring or an 8-10 member heteroaromatic bicyclic ring system, each ring or ring system containing a carbon atom and 1-4 heteroatoms independently selected from up to two oxygen atoms, up to two sulfur atoms, and up to four nitrogen atoms, the up to three carbon ring members being independently selected from C(=O) and C(=S), and the sulfur ring member being S(=O) u (=NR 8 ) v Independently selected from, each ring or ring system has R on the carbon atom ring member. 10R on the nitrogen atom ring member is selected independently from 11 It is optionally substituted with up to 5 substituents selected from the following: Y 1 and Y 2 These are O, S, or NR, respectively, independently. 12 And, R 1 H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C4-C8 cycloalkylalkyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C1-C 10 Trialkylsilyl, or G 1 And, R 2 and R 3 Each of these is independently either H, a halogen, or a C1-C4 alkyl, or R 2 and R 3 These, together with the carbon atoms to which they are bonded, form a C3-C7 cycloalkyl ring. R 4 and R 5Each of these is independently H, a halogen, or a C1-C4 alkyl group. R 6 H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C4~C 10 Alkylaminocarbonyl, C3~C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 Trialkylsilyl or G 1 And, Each R 7 and R 10 These are independently halogen, cyano, nitro, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, and C4-C 10 Cycloalkylalkyl, C4~C 10 Halocycloalkylalkyl, C5~C 12 Alkylcycloalkylalkyl, C5~C 12 Cycloalkylalkenyl, C5~C 12Cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C 10 Alkylcycloalkyl, C6~C 12 Cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C3-C8 haloalkoxyalkoxy, C3-C8 alkoxyalkoxy, C4-C 10 Cycloalkoxyalkyl, C3-C 10 Alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C 10 Cycloalkylaminoalkyl, C3~C 10 Dialkylaminoalkyl, -CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, -C(=O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, -C(=O)NH2, C2~C8 alkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C3~C 10 Dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C 10 Cycloalkylalkoxy, C3-C 10 Alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C 10Cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, -SF5, -SCN, SO2NH2, C3-C 12 Trialkylsilyl, C4~C 12 Trialkylsilylalkyl, C4~C 12 Trialkylsilylalkoxy or G 2 And, Each R 8 These are independently H, cyano, C2-C3 alkylcarbonyl, or C2-C3 haloalkylcarbonyl. Each R 9 and R 11 These are independently cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl, or C3-C4 dialkylaminoalkyl. Each R 12 These are independently H, cyano, C1-C4 alkyl, C1-C4 haloalkyl, -(C=O)CH3, or -(C=O)CF3. each G 1 These are independently phenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenoxy, phenylethynyl, phenylsulfonyl, or a 5-membered or 6-membered heteroaromatic ring, each of which is R 13 The ring members are optionally substituted with up to five substituents independently selected from the compound, each G 2These are independently phenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenoxy, phenylethynyl, phenylsulfonyl, or a 5-membered or 6-membered heteroaromatic ring, each of which is R 14 The ring members are optionally substituted with up to five substituents independently selected from the compound, Each R 13 and R 14 These are independently halogen, cyano, hydroxy, amino, nitro, -CHO, -C(=O)OH, -C(=O)NH2, -SO2NH2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, and C4-C 10 Cycloalkylcarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 These are trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, phenyl, pyridinyl, or thienyl. Each u and v is S(=O) u (=NR 8 ) v In each of these cases, independently, the values ​​are 0, 1, or 2, provided that the sum of u and v is 0, 1, or 2. however, (a) The compound of formula 1 is any compound other than N-1H benzotriazol-1-yl-2-oxo-4-phenyl-3-pyrrolidinecarboxamide, (b)Q 1If the remaining part of formula l contains a 3-furanyl ring or a 3-pyridinyl ring directly bonded to it, then the ring is R 7 It is substituted with at least one substituent selected from the following: (c)Q 1 is an unsubstituted phenyl ring, and Q 2 If Q contains a phenyl ring directly bonded to the rest of formula 1, then Q 2 The ring is R unless it is optionally substituted with phenoxy or F at position 2 and cyano or -CF3 at position 4. 10 It is replaced with R 5 is H or halogen, (d)Q 1 is an unsubstituted phenyl, and Q 2 If the remaining part of formula 1 contains a pyridinyl ring directly bonded to it, then the pyridinyl ring is R 10 It is substituted with at least one substituent selected from the following: (e)Q 1 If Q is a phenyl ring substituted with 4-phenyl or 4-phenoxy, then Q 1 The ring is R 7 It is further replaced by, (f)Q 1 The compound contains a phenyl ring directly bonded to the rest of formula I, and the ring is bonded to both ortho positions (relative to the bond with the rest of formula I) 7 If substituted, the ring also independently has R at at least one additional position. 7 It has been replaced with, (g)Q 1 If Q is an unsubstituted 1-naphthalenyl, 2 is other than 2,3-diylorophenyl or 2-CF3-phenyl, (h)Q 2 This is any other than the optionally substituted 1H-pyrazole-5-yl, (i)Q 2 If the remaining part of formula I contains a 1H-pyrazole-3-yl ring directly bonded to it, then the ring is R 9 It has been replaced in first place.

[0120] Embodiment A35b The following structure [ka] A saturated target having the following structure, which is combined, miscible, mixed, etc. with at least one unsaturated precursor defined by any of the following: [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 3 , R 4 (R6, Y1 and Y2, etc., have the meanings defined in claim 1 of PCT / US2014 / 068073, published as International Publication No. 2015 / 084796). The text extracted from claim 1, from page 286, line 6 to page 289, line 23 of International Publication No. 2015 / 084796, is incorporated specifically by reference solely for the purpose of defining the structure of this embodiment. Text reproduced in Embodiment A35a.

[0121] Embodiment A35c The following structure [ka] A saturated target having the following structure, which is a combination, miscible, or mixed with at least one unsaturated precursor that is an unsaturated precursor defined by any of the following: [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 3 , R 4(R6, Y1 and Y2, etc., have the meanings defined in claim 1 of PCT / US2014 / 068073, published as International Publication No. 2015 / 084796). The text extracted from claim 1, from page 286, line 6 to page 289, line 23 of International Publication No. 2015 / 084796, is incorporated specifically by reference solely for the purpose of defining the structure of this embodiment. Text reproduced in Embodiment A35a.

[0122] Embodiment A36a The following structure [ka] A saturated target having the following structure, which is combined, miscible, mixed, etc. with at least one unsaturated precursor defined by any of the following: [ka] (In the formula, Q, R 1 , R 6 (Y and W, etc., have the meanings defined in claim 1 of PCT / US2020 / 034232, published as International Publication Brochure 2020 / 242946). The text of claim 1 from page 87, line 3 to page 88, line 6 of International Publication Brochure 2020 / 242946 is incorporated herein by reference solely for the purpose of defining the structure of this embodiment.

[0123] In the equation, Q is [ka] Selected from the group consisting of, R 1 These are H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl. R 2 These are C1-C6 alkyl or C1-C6 haloalkyl, R 3These are halogens, C1-C6 alkyls, C1-C6 haloalkyls, C1-C6 alkoxys, or C1-C6 haloalkoxys. Y is either O or S, R 4 These are H, halogen, C1-C4 alkyl, or C1-C4 haloalkyl. R 5 These are halogens, C1-C4 alkyls, or C1-C4 ahaloalkyls. n is 1, 2, 3, or 4. R 6 These are H, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 haloalkyl, or C1-C4 alkyl. W is phenyl or pyridyl, and each phenyl or pyridyl may have up to 5 R 9 It is arbitrarily replaced with, Each R 9 These are independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C1-C4 nitroalkyl, C2-C4 nitroalkenyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C1-C4 alkoxy, C1-C4 haloalkoxy Xy, C1-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy. C3-C4 haloalkynyloxy, C3-C4 cycloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, hydroxy, formyl, C2-C4 alkylcarbonyl, C2-C4 alkylcarbonyloxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, amino, C1-C4 alkylamino, C2-C4 dialkylamino, formylamino. C2-C4 alkylcarbonylamino, -SF5, -SCN, C3-C4 trialkylsilyl, trimethylsilylmethyl or trimethylsilylmethoxy, However, if the compound is Q-1, R 1 H is R 2 CH3 is, R 3 is C(CH3)3, and R 4 H is R 6 H is , Y is 0, W is 2nd and R 9 A phenyl substituted with R 9 It is a compound other than the compound of formula 1 in which F is present.

[0124] Embodiment A37a An unsaturated precursor defined by one of the following structures, [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 7 Y, A, and J, etc., have the meanings defined in Claim 1 of PCT / US2016 / 030450, which was published as International Publication Brochure No. 2016182780. The text of Claim 1, from page 101, line 3 to page 106, line 28 of International Publication Brochure No. 2016 / 182780, is incorporated by reference specifically for the purpose of defining the structure of this embodiment.

[0125] Q 1 The rings are phenyl or benzyl rings, or naphthalenyl ring systems, each ring or ring system being optionally substituted with up to 5 substituents independently selected from R, or being a 5-6 membered completely unsaturated heterogroup ring or an 8-10 membered heteroaromatic bicyclic ring system, each ring or ring system containing a carbon atom and 1-4 heteroatoms independently selected from up to 2 oxygen atoms, up to 2 sulfur atoms, and up to 4 nitrogen atoms, the up to 3 carbon ring members being independently selected from C(=O) and C(=S), and the sulfur ring member being S(=O) u (=NR 8 ) v Independently selected from, each ring or ring system has R on the carbon atom ring member. 9R on the nitrogen atom ring member is selected independently from 10 It is optionally substituted with up to 5 substituents selected from the following: Q 2 This is a phenyl ring or naphthalenyl ring system, and each ring or ring system is R 11 The rings are optionally substituted with up to five substituents independently selected from the carbon atoms, or are 5-6 membered fully unsaturated heterogroup rings or 8-10 membered heteroaromatic bicyclic ring systems, each ring or ring system containing a carbon atom and 1-4 heteroatoms independently selected from up to two oxygen atoms, up to two sulfur atoms, and up to four nitrogen atoms, with up to three carbon ring members independently selected from C(=O) and C(=S), and sulfur ring members being S(=O) u (=NR 8 ) v Independently selected from, each ring or ring system has R on the carbon atom ring member. 11 R on the nitrogen atom ring member is selected independently from 12 It is optionally substituted with up to 5 substituents selected from the following: R 1 and R 2 Each of these is independently H, halogen, hydroxyl, or C1-C4 alkyl. Y is O, S, or NR 15 And, A is a saturated, partially unsaturated, or fully unsaturated chain containing 2 to 4 atoms selected from up to 4 carbon atoms, up to 1 oxygen atom, up to 1 sulfur atom, and up to 2 nitrogen atoms, wherein up to 2 carbon members are independently selected from C(=O) and C(=S), and the sulfur member is S(=O). u (=NR 8 ) v Selected from, the chain has R on carbon atoms. 3 and R on the nitrogen atom 4 It is optionally substituted with up to 5 substituents independently selected from the original compound. Each R 3These are independently halogens, cyano, hydroxy, -CO2H, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, C3-C6 cycloalkyl, or C4-C6 cycloalkylalkyl, or Two R's 3 These, together with the carbon atoms to which they are bonded, form a C3-C7 cycloalkyl ring. Each R 4 These are independently cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, or C3-C6 cycloalkyl. J is -CR 5 R 6 - or CR 5 R 6 -CR 5a R 6a And, -CR 5 R 6 The part is directly bonded to N, R 5 and R 6 Each of these is independently H, halogen, hydroxyl, C1-C4 alkyl, or C1-C4 alkoxy. R 5 and R 6 These, together with the carbon atoms to which they are bonded, form a C3-C7 cycloalkyl ring. R 5a and R 6a Each of these is independently either H, a halogen, or a C1-C4 alkyl, or R 5a and R 6a These, together with the carbon atoms to which they are bonded, form a C3-C7 cycloalkyl ring. R 7H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 Trialkylsilyl or G 1 And, Each R 8 These are independently H, cyano, C2-C3 alkylcarbonyl, or C2-C3 haloalkylcarbonyl. Each R 9 These are independently halogen, cyano, nitro, C1-C8 alkyl, C1-C4 cyanoalkyl, C1-C4 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C4-C 10 Cycloalkylalkyl, C4~C 10 Halocycloalkylalkyl, C5~C 12 Alkylcycloalkylalkyl, C5~C 12 Cycloalkylalkenyl, C5~C 12Cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C 10 Alkylcycloalkyl, C6~C 12 Cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C2 ~C8 haloalkoxyalkyl, C3~C8 haloalkoxyalkoxy, C1~C4 hydroxyalkyl, C1~C 10 Cycloalkoxyalkyl, C3-C 10 Alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C 10 Cycloalkylaminoalkyl, C3~C 10 Dialkylaminoalkyl, -CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, -C(=O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, -C(=O)NH2, C2~C8 alkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C3~C 10 Dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C2-C8 haloalkoxyhaloalkoxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C 10 Cycloalkylalkoxy, C3-C 10 Alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C 10Cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, -SF5, -SCN, SO2NH2, C3-C 12 Trialkylsilyl, C4~C 12 Trialkylsilylalkyl, C4~C 12 Trialkylsilylalkoxy or G 2 And, Each R 11 These are independently halogen, cyano, nitro, C1-C8 alkyl, C1-C4 cyanoalkyl, C1-C4 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C4-C 10 Cycloalkylalkyl, C4~C 10 Halocycloalkylalkyl, C5~C 12 Alkylcycloalkylalkyl, C5~C 12 Cycloalkylalkenyl, C5~C 12 Cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C 10 Alkylcycloalkyl, C6~C 12 Cycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C3-C8 haloalkoxyalkoxy, C1-C4 hydroxyalkyl, C4-C 10 Cycloalkoxyalkyl, C3-C 10Alkylsulfonylalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C 10 Cycloalkylaminoalkyl, C4~C 10 Dialkylaminoalkyl, -CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, -C(=O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, -C(=O)NH2, C2~C8 alkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C3~C 10 Dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C2-C8 haloalkoxyhaloalkoxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C 10 Cycloalkylalkoxy , C3~C 10 Alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C 10Cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, -SF5, -SCN, SO2NH2, C3-C 12 Trialkylsilyl, C4~C 12 Trialkylsilylalkyl, C4~C 12 Trialkylsilylalkoxy or G 3 And, Each R 10 and R 12 These are independently cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl, or C3-C4 dialkylaminoalkyl. R 15 These are H, cyano, C1-C4 alkyl, C1-C4 haloalkyl, -(C=O)CH3, or -(C=O)CF3. each G 1 These are independently phenyl, phenylmethyl, pyridinylmethyl, pyridinyloxy, phenylcarbonyl, phenoxy, phenylethynyl, phenylsulfonyl, phenylcarbonyl (C1-C4 alkyl), or a 5-membered or 6-membered heteroaromatic ring, each of which is R 13 The ring members are optionally substituted with up to five substituents independently selected from the compound, each G 2These are independently phenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenylcarbonylalkyl, phenoxy, phenylethynyl, phenylsulfonyl, or pyridyloxy, or each of them is R 14 A 5-membered or 6-membered heteroaromatic ring whose ring members are optionally substituted with up to 5 substituents independently selected from, or R 16 ON=CR 17 -, (R 18 )2C=NO-, (R 19 )2NN=CR 17 -, (R 18 )2C=NNR 20 -, R 21 N=CR 17 -, (R 18 )2C=N-, R 22 ON=CR 17 C(R 23 )2-, or (R 18 )2C=NOC(R 23 )2-, and the free bond protruding to the right is Q 1 It shows the connection point to, each G 3 These are independently phenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenylcarbonylalkyl, phenoxy, phenylethynyl, phenylsulfonyl, phenylcarbonyl (C1-C4 alkyl), or a 5-membered or 6-membered heteroaromatic ring, each of which is R 15 The ring members are optionally substituted with up to five substituents independently selected from the compound, Each R 13 , R 14 and R 15 These are independently halogen, cyano, hydroxy, amino, nitro, -CHO, -C(=O)OH, -C(=O)NH2, -SO2NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, and C4-C 10 Cycloalkoxycarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C10 Dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 These are trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, or C1-C6 alkylsulfonylamino. Each R 16 These are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4- C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 Trialkylsilyl or G 1 And, Each R 17These are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C3-C 10 Trialkylsilyl or G 1 And, Each R 18 These are independently H, hydroxy, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 Trialkylsilyl or G 1 And, Each R 19These are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C4~C 10 Alkylaminocarbonyl, C3~C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 It is a trialkylsilyl or G1, Each R 20 These are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy C3-C 10 Trialkylsilyl or G 1 And, Each R 21These are independently H, hydroxy, amino, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 It is a trialkylsilyl or G1, Each R 22 These are independently H, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, or C1-C6 cycloalkyl. Each R 23 These are independently H, halogen, cyano, hydroxy, C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylcarbonyl, C2-C4 alkoxycarbonyl, or C3-C6 cycloalkyl. Each u and v is S(=O) u (=NR 8 )v In each of these cases, independently, the values ​​are 0, 1, or 2, provided that the sum of u and v is 0, 1, or 2, provided that the compound is Q 1 Ph(3-CF3), Q 2 Ph(2-F) and R 1 H is R 2 H is H, Y is O, A is -CH2CH2-, and J is -CR 5 R 6 - and R 5 H is R 6 H is R 7 These are compounds other than those in which H is present.

[0126] Embodiment A37b A pesticide synthesis intermediate compound defined by one of the following structures, [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 7 (Y, A, and J, etc., have the meanings defined in Claim 1 of PCT / US2016 / 030450, which was published as International Publication Brochure 2016 / 182780). The text of Claim 1, from page 101, line 3 to page 106, line 28 of International Publication Brochure 2016 / 182780, is incorporated by reference specifically for the purpose of defining the structure of this embodiment, and this text is reproduced in Embodiment A37a.

[0127] Embodiment A37c The following structure [ka] A saturated target having the following structure, which is combined, miscible, mixed, etc. with at least one unsaturated precursor defined by any one of the following: [ka] (In the formula, Q 1 Q2 , R 1 , R 2 , R 7 (Y, A, and J, etc., have the meanings defined in Claim 1 of PCT / US2016 / 030450, which was published as International Publication Brochure No. 2016182780). The text of Claim 1, from page 101, line 3 to page 106, line 28 of International Publication Brochure No. 2016 / 182780, is incorporated by reference specifically for the purpose of defining the structure of this embodiment, and this text is reproduced in Embodiment A37a.

[0128] Embodiment A38 An unsaturated precursor defined by one of the following formulas, [ka] (In the formula, Q 1 Q 2 , R B1 (and X etc. have the meanings defined in claim 1 of PCT / EP2020 / 052780, which was published as International Publication Brochure 2020 / 161147). The text from claim 1 on page 74, line 10 to page 75, line 10 of International Publication Brochure 2020 / 161147 is incorporated by reference specifically for the purpose of defining the structure of this embodiment.

[0129] R B1 is H, methyl, or methoxy, X is either O or S, Q 1 R on one ring nitrogen B2 Substituted by and on at least one ring carbon R B3 A di-substituted or tri-substituted pyrazole substituted by, R B2 These are C1-C3 alkyl or C1-C3 fluoroalkyl, and each R B3Independently, is a halogen, C1-C3 fluoroalkyl, C1-C3 haloalkoxy, C1-C3 alkoxy, or C1-C3 haloalkyl, C1-C3 fluoroalkyl, C1-C3 haloalkoxy, C1-C3 alkoxy, or C1-C3 alkyl, or Q 1 R on one ring nitrogen B2 Therefore, R on adjacent ring carbons 53 It is a disubstituted pyrazole substituted with R B2 It is a C1-C3 alkyl group, and R B3 R is a C1-C3 fluoroalkyl or CC1-C3 alkyl, B2 and R B3 These, together with the atoms to which they are bonded, form an 8- or 9-membered fused heterocyclic bicyclic system. Q 2 This can be any 1, 2, or 3 R B5 Phenyl, pyridinyl, substituted with substituents or it is a thienyl ring system, Each R B5 These are independently halogens, C1-C6 alkyls, C1-C6 haloalkyls, C1-C6 alkoxys, C1-C6 haloalkoxys, cyanos, nitros, C1-C6 alkylthios, C1-C6 alkylsulfinyls, or C1-C6 alkylsulfonyls, or N-oxides or salts thereof.

[0130] Embodiment A38a Each has the following structure [ka] A combination, miscible, or mixed with at least one unsaturated precursor defined by any one of the saturated targets described in claim 1 of PCT / EP2020 / 052780, published as international publication brochure 2020 / 161147, [ka] (In the formula, Q 1 Q 2 , R B1(and X etc. have the meanings defined in claim 1 of PCT / EP2020 / 052780, which was published as International Publication Brochure 2020 / 161147). The text from claim 1 on page 74, line 10 to page 75, line 10 of International Publication Brochure 2020 / 161147 is incorporated by reference specifically for the purpose of defining the structure of this embodiment, and the text is reproduced in Embodiment A38.

[0131] Embodiment A39 An unsaturated precursor defined by one of the following formulas, [ka] (In the formula, Q, W 2 , R 1 (Y and Z, etc., have the meanings defined in claim 1 of PCT / EP2018 / 069001, which was published as International Publication Brochure No. 2019 / 025156). The German text from claim 1 on page 109, line 3 to page 112, line 6 of International Publication Brochure No. 2019 / 025156 is incorporated by reference specifically for the purpose of defining the structure of this embodiment.

[0132] Embodiment A40 An unsaturated precursor having the following structure. [ka]

[0133] Embodiment A41 An unsaturated precursor defined by one of the following structures, [ka] (In the formula, Q 1 Q 2 , R 1 , R 7 , R 9 , J, L, Y and Y 2(These terms have the meanings defined in claim 1 of PCT / US2018 / 035017, which was published as International Publication Brochure No. 2018 / 222647). The text of claim 1 from page 84, line 5 to page 89, line 27 of International Publication Brochure No. 2018 / 222647 is incorporated by reference specifically for the sole purpose of defining the structure of this embodiment.

[0134] L is selected from the following: [ka] and R A These are C1-C7 alkyl, C1-C7 haloalkyl, C3-C9 cycloalkyl, C3-C9 halocycloalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C3-C9 cycloalkoxy, C3-C9 halocycloalkoxy, C2-C8 alkenyl, C2-C8 haloalkenyl, C1-C7 alkylalumino, C1-C7 haloalkylamino, C2-C9 dialkylamino, C2-C9 halodialkylamino, C3-C9 cycloalkylamino, or C3-C9 halocycloalkylamino, and each is R 8 It may be substituted or unsubstituted with up to three substituents independently selected from G 1 is, or R A G 1 Or OG 1 is, or R A -C(R I )(R J )C(=O)- and R 9 Joining together, R B is H, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 alkyl, or a phenyl that is substituted with a halogen or C1-C4 alkyl or is unsubstituted. R Cis H, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 alkyl, or a phenyl that is substituted with a halogen or C1-C4 alkyl or is unsubstituted. R D is H, C1-C4 alkyl, or C2-C4 alkylcarbonyl, R E H, hydroxy, amino, cyano, formyl, -C(O)NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C4-C8 cycloalkylalkyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyarsyl, C2-C8 haloalkoxyalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkenylalkyl, C2-C8 haloalkenylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkyl carbonyl C5~C 10 Cycloalkyl carbonyl alkyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Gial Killaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkyllysulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl or C2-C8 dialkylaminosulfonyl, or G E Or W E G E And, R F These are H, formyl, -C(O)NH2, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, -P(=O)(OH)2-, C1-C6 dialkylphosphoryl, C1-C6 haloalkylphosphoryl, C3-C8 cycloalkylphosphoryl, C2-C8 dialkoxyphosphoryl, C6-C 14 Dicycloalkoxyphosphoryl, C2~C 12 Bis(alkylamino)phosphoryl, C4~C 24 Bis(dialkylamino)phosphoryl, or G F Or W F G F And, R G These are formyl, -C(O)NH2, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, -P(=O)(OH)2, C1-C6 dialkylphosphoryl, C1-C6 haloalkylphosphoryl, C2-C8 cycloalkylphosphoryl, C2-C8 dialkoxyphosphoryl, C6-C 14 Dicycloalkoxyphosphoryl, C8~C 16Dicycloalkylalkoxyphosphoryl, C2~C 12 Bis(alkylamino)phosphoryl, C4~C 24 Bis(dialkylamino)phosphoryl, or phenyl or R 16 It is either substituted or not substituted, or W G G G And, R I is H, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 alkyl, or a phenyl that is substituted with a halogen or C1-C4 alkyl or is unsubstituted. R J is H, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 alkyl, or a phenyl that is substituted with a halogen or C1-C4 alkyl or is unsubstituted. Q 1 This is a phenyl ring or naphthalenyl ring system, and each ring or ring system is R 7 It is substituted with up to five substituents independently selected from or unsubstituted, or is a 4- to 7-membered heterogroup ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system containing a carbon atom and 1 to 5 heteroatoms independently selected from up to 2 oxygen atoms, up to 2 sulfur atoms, and up to 5 nitrogen atoms, the up to 3 carbon ring members being independently selected from C(=O) and C(=S), and the sulfur ring member being S(=O) u (=NR 14 ) v Independently selected from, each ring or ring system has R on the carbon atom ring member. 10 R on the nitrogen atom ring member is selected independently from 12 It is optionally substituted with up to 5 substituents selected from, or Q 2 This is a phenyl ring or naphthalenyl ring system, and each ring or ring system is R 10 It is substituted with or unsubstituted with up to 5 substituents independently selected from, or A heteroaromatic bicyclic ring system of 4-7 membered complex rings or 8-10 membered rings, where each ring or ring system contains a carbon atom and 1-4 heteroatoms independently selected from up to 2 oxygen atoms, up to 2 sulfur atoms, and up to 5 nitrogen atoms, where up to 3 carbon ring members are independently selected from C(=O) and C(=S), and the sulfur ring member is S(=O) u (=NR 14 ) v Independently selected from, each ring or ring system has R on the carbon atom ring member. 11 R on the nitrogen atom ring member is selected independently from 13 It is optionally substituted with up to 5 substituents selected from, or J is -CR 2 R 3 -, -CR 2 R 3 -CR 4 R 5 -, -NR 6 - or O- Y 1 and Y 2 These are O, S, or NR, respectively, independently. 15 And, R 1 H, hydroxy, amino, cyano, formyl, C3-C8 alkylcarbonylalkyl-C(C1-C4 alkyl)=NO(C1-C4 alkyl), -C(O)NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C8 cycloalkenyl, C4-C8 cycloalkylalkyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkenylalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C5~C 10 Cycloalkylcarbonylalkyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10Cycloalkoxycarbonyl C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 Trialkylsilyl, or -CPh=NO(C1~C4 alkyl), where each is R 13 It may be substituted with up to 5 substituents independently selected from or unsubstituted with G 1 And, R 2 and R 3 Each of these is independently H, halogen, hydroxyl, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy, or R 2 and R 3 These, together with the carbon atoms to which they are bonded, form a C3-C7 cycloalkyl ring. R 4 and R 5 Each of these is independently H, halogen, hydroxyl, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy. R 6 is either C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl or C1-C6 alkoxy, or R 1 and R 6 These combine as C3-C6 alkylenes or -CH2OCH2-. R 7 These are H, halogen, hydroxyl, C1-C4 alkoxy, C1-C4 haloalkyl, or C1-C4 alkyl. R 8These are, independently, cyano, hydroxy, amino, nitro, -CHO, -C(=O)OH, -C(=O)NH2, -SO2NH2, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, and C4-C 10 Cycloalkoxycarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 Trialkyl These are lyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, or C1-C6 alkylsulfonylamino. R 9 H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, or C3-C 10 Trialkylsilyl, or G 1 And, Each R 10 and R 11 These are independently halogen, hydroxy, cyano, nitro, amino, C1-C8 alkyl, C1-C8 cyanoalkyl, C1-C8 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 hydroxyalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C4-C 10 Cycloalkylalkyl, C4~C 10 Halocycloalkylalkyl, C5~C 12 Alkylcycloalkylalkyl, C5~C 12 Cycloalkylalkenyl, C5~C 12 Cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C 10 Alkylcycloalkyl, C6~C 12 Cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C1-C8 haloalkoxyalkoxy, C2-C8 alkoxyalkoxy, C4-C 10Cycloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C 10 Cycloalkylaminoalkyl, C3~C 10 Dialkylaminoalkyl, -CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylarbonyl, C4-C 10 Cycloalkylcarbonyl, monoC(=O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, -C(=O)NH2, C2~C8 alkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C3~C 10 Dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C 10 Cycloalkylalkoxy, C3-C 10 Alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C 10 Cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C3-C8 cycloalkylamino, C2-C8 alkoxycarbonylamino, C1-C 6-alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, -SF5, -SCN, SO2NH2, C3-C 12 Trialkylsilyl, C4~C 12 Trialkylsilylalkyl or C4~C 12 Trialkylsilylalkoxy, or G 2 is or R 20 S(=O)=N-, R 20 S(=O)2NR 19 -C(=O)- or R 20 (R 19 N=) q S(=O) p - and the free bond protruding to the right is Q 1 It indicates a connection point to, or Each R 12 and each R 13 These are, independently, cyano C1-C3 alkyl, C1-C8 hydroxyalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl, or C3-C4 dialkylaminoalkyl. Each R 14 Each R is independently H, cyano, C2-C3 alkylcarbonyl, or C2-C3 haloalkylcarbonyl, and each R 15 These are independently H, cyano, hydroxy, CHO, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, -(C=O)CH3, or (C=O)CF3. each G 1 These are independently phenyl or a 5-membered or 6-membered heterocyclic ring, each being R 17 It is substituted with up to 5 substituents independently selected from, or it is unsubstituted. Each W E , W F and W G These are independently -C(=O)-, -C(=O)O-, -C(=O)NH-, or -S(=O)2-, each GE , G F and G G R is independent of R 16 It is a substituted or unsubstituted phenyl, or a 5-membered or 6-membered heterocyclic ring, Each complex ring is R 16 The ring members are substituted with up to five substituents independently selected from, or are unsubstituted. each G 2 These are independently phenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenoxy, phenylethynyl, phenylsulfonyl, or a 5-membered or 6-membered heterocyclic ring, each of which is R 18 The ring members are substituted with up to five substituents independently selected from, or are unsubstituted. Each R 16 , R 17 and R 18 These are independently halogen, cyano, hydroxy, amino, nitro, -CHO, -C(=O)OH, -C(=O)NH2, -SO2NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8 alkoxycarbonyl, and C4-C 10 Cycloalkylcarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 These are trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, phenyl, pyridinyl, or thienyl. Each R19 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3 haloalkylcarbonyl, each R 20 is independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 aikylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy or C3-C 10 trialkylsilyl, or G 1 and each u and v is S(=O) u (=NR 14 ) v in each case is independently 0, 1 or 2, provided that the sum of u and v is 0, 1 or 2, each p and q is R 20 (R 19 N=) q S(=O) p - in each case is independently 0, 1 or 2, provided that the sum of u and v is 0, 1 or 2 and q is other than 1 or 2 when p is 0.

[0135] Embodiment A41a each of the following structures

Chemical formula

Chemical formula

[0136] Embodiment A42 An unsaturated precursor defined by any one of the following formulas, [ka] (In the formula, Q 1 Q 2 , R 1 , R 7 , R 8 , R 9 (J, Y, and W, etc., have the meanings defined in claim 1 of PCT / US2018 / 035015, which was published as International Publication Brochure 2018 / 222646). The text of claim 1 from page 82, line 6 to page 86, line 21 of International Publication Brochure 2018 / 222646 is incorporated by reference specifically for the sole purpose of defining the structure of this embodiment.

[0137] W is -NR A R B OR C And, R A is a phenyl that is substituted with or unsubstituted with H, cyano, CHO, C1-C4 alkylcarbonyl, C1-C4 alkyl, halogen or C1-C4 alkyl, R BH, cyano, hydroxy, CHO, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cyclosulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, or C3-C 10 A trialkylsilyl, or a phenyl ring or a naphthalenyl ring, and each ring or ring system is R 16 It may be substituted with up to 5 substituents independently selected from or unsubstituted, or R 16 A 4- to 7-membered heterocyclic linkage that is substituted with or unsubstituted by up to 5 substituents independently selected from, or R A and R B These atoms, together with the nitrogen atoms to which they are bonded, form 4, 5, or 6-membered rings containing ring members selected from carbon, oxygen, nitrogen, and C(=O)-, or they come together as 6- to 10-membered bicyclic relationships, or as 8- to 13-membered acidic cyclic systems, each ring or system containing ring members selected from carbon, nitrogen, and -C(=O)-, and being substituted or unsubstituted with halogens, cyano or C1-C4 alkyl groups. R CThis is a C1-C4 haloalkyl, C2-C4 haloalkylcarbonyl, C3-C6 cycloalkyl, or a phenyl substituted or unsubstituted with a halogen, cyano, or C1-C4 alkyl, or a 6-membered nitrogen-containing aromatic ring substituted or unsubstituted with a halogen, cyano, or C1-C4 alkyl. J is -CR 2 R 3 -, -CR 2 R 3 -CR 4 R 5 -, -NR 6 - or O- Y is O, S, or NR 15 And, R 1 H, hydroxy, amino, cyano, CHO, C3-C8 alkylcarbonylalkyl, C(C1-C4 alkyl)=NO(C1-C4 alkyl), -C(O)NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C8 cycloalkenyl, C4-C8 cycloalkylalkyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl. C2-C8 haloalkenylalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C5~ 10 Cycloalkylcarbonylalkyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 Trialkylsilyl, or Cph=NO(C1~C4 alkyl)(phenyl is R) 13 (Substituted with or unsubstituted with up to 5 substituents independently selected from G) or G 1 And, Q 1 This is a phenyl ring or naphthalenyl ring system, and each ring or ring system is R 11 mosquito The rings are substituted with up to five substituents independently selected from the carbon atoms, or are unsubstituted, or are 4-7 membered heterogroup rings or 8-10 membered heteroaromatic bicyclic ring systems, each ring or ring system containing a carbon atom and 1-4 heteroatoms independently selected from up to two oxygen atoms, up to two sulfur atoms, and up to five nitrogen atoms, with up to three carbon ring members independently selected from C(=O) and C(=S), and sulfur ring members being S(=O) u (=NR 14 ) v Independently selected from, each ring or ring system has R on the carbon atom ring member. 11 R on the nitrogen atom ring member is selected independently from 13 It is optionally substituted with up to 5 substituents selected from the following: Q 2 This is a phenyl ring or naphthalenyl ring system, and each ring or ring system is R 11is substituted with up to 5 substituents independently selected therefrom or is unsubstituted, or is a 4- to 7-membered heterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ring system, each ring or ring system containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O atoms, up to 2 S atoms and up to 5 N atoms, up to 3 carbon ring members being independently selected from C(=O) and C(=S), and sulfur atom ring members being S(=O) u (=NR 14 ) v independently selected from, and each ring or ring system being optionally substituted with up to 5 substituents selected from R 11 independently selected from on carbon atom ring members and R 13 selected from on nitrogen atom ring members R 2 and R 3 are each independently H, halogen, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy, or R 2 and R 3 together with the carbon atom to which they are attached form a C3-C7 cycloalkyl ring R 4 and R 5 are each independently H, halogen, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy R 6 is C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl or C1-C6 alkoxy R 1 and R 6 together are C3-C6 alkylene or -CH2OCH2 R 7 and R 8 are each independently H, halogen, hydroxy, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 alkyl R 9H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C6 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10 Trialkylsilyl, or G 1 And, R 10 and R 11 These are, independently, halogen, hydroxy, cyano, nitro, amino, C1-C8 alkyl, C1-C8 cyanoalkyl, C1-C8 cyanoalkoxy, C1-C8 haloalkyl, C1-C8 hydroxyalkyl, C1-C8 nitroalkyl, C2-C8 alkenyl, C2-C8 haloalkenyl, C2-C8 nitroalkenyl, C2-C8 alkynyl, C2-C8 haloalkynyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 haloalkoxyhaloalkoxy, C3-C6 cycloalkyl, cyclopropylmethyl, 1-methyl Tylcyclopropyl, 2-methylcyclopropyl, C4~C 10 Cycloalkylalkyl, C4~C 10Halocycloalkylalkyl, C5~C 12 Alkylcycloalkylalkyl, C5~C 12 Cycloalkylalkenyl, C5~C 12 Cycloalkylalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, C4-C 10 Alkylcycloalkyl, C6~C 12 Cycloalkylcycloalkyl, C3-C8 cycloalkenyl, C3-C8 halocycloalkenyl, C2-C8 haloalkoxyalkoxy, C2-C8 alkoxyalkoxy, C4-C 10 Cycloalkoxyalkyl, C3-C 10 Alkoxyalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylamino, C2-C8 dialkylamino, C2-C8 halodialkylamino, C2-C8 alkylaminoalkyl, C2-C8 haloalkylaminoalkyl, C4-C 10 Cycloalkylaminoalkyl, C3~C 10 Dialkylaminoalkyl, -CHO, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C 10 Cycloalkylcarbonyl, -C(=O)OH, C2-C8 alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C 10 Cycloalkoxycarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, -C(=O)NH2, C2~C8 alkylaminocarbonyl, C4~C 10 Cycloalkylaminocarbonyl, C3~C 10 Dialkylaminocarbonyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C2-C8 alkoxyalkoxy, C2-C8 alkenyloxy, C2-C8 haloalkenyloxy, C3-C8 alkynyloxy, C3-C8 haloalkynyloxy, C3-C8 cycloalkoxy, C3-C8 halocycloalkoxy, C4-C 10 Cycloalkylalkoxy, C3-C 10Alkylcarbonylalkoxy, C2-C8 alkylcarbonyloxy, C2-C8 haloalkylcarbonyloxy, C4-C 10 Cycloalkylcarbonyloxy, C1-C8 alkylsulfonyloxy, C1-C8 haloalkylsulfonyloxy, C1-C8 alkylthio, C1-C8 haloalkylthio, C3-C8 cycloalkylthio, C1-C8 alkylsulfinyl, C1-C8 haloalkylsulfinyl, C1-C8 alkylsulfonyl, C1-C8 haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, formylamino, C2-C8 alkylcarbonylamino, C2-C8 haloalkylcarbonylamino, C3-C8 cycloalkylamino, C2-C8 alkoxycarbonylamino, C1-C6 alkylsulfonylamino, C1-C6 haloalkylsulfonylamino, -SF5, -SCN, SO2NH2, C3-C 12 Trialkylsilyl, C4~C 12 Trialkylsilylalkyl or C4~C 12 Trialkylsilylalkoxy, or G2, or R 20 S(=O)=N-, R 20 S(=O)2NR 19 -C(=O)- or R 20 (R 19 N=) q S(=O) p - and the free bond protruding to the right is Q 1 It shows the connection point to, Each R 12 and each R 13 These are, independently, cyano C1-C3 alkyl, C1-C8 hydroxyalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl, or C3-C4 dialkylaminoalkyl. Each R 14 These are independently H, cyano, C2-C3 alkylcarbonyl, or C2-C3 haloalkylcarbonyl. R 15These are H, cyano, hydroxy, CHO, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C2-C6 alkylcarbonyl, or C2-C6 haloalkylcarbonyl. each G 1 These are independently phenyl or a 5-membered or 6-membered heterocyclic ring, each being R 17 It is substituted with up to 5 substituents independently selected from, or it is unsubstituted. each G 2 These are independently phenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenoxy, phenylethynyl, phenylsulfonyl, or a 5-membered or 6-membered heterocyclic ring, each of which is R 18 The ring members are substituted with up to five substituents independently selected from, or are unsubstituted. Each R 16 , R 17 and R 18 These are independently halogen, cyano, hydroxy, amino, nitro, -CHO, -C(=O)OH, -C(=O)NH2, -SO2NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C8 alkylcarbonyl, C1-C8 hydroxyalkyl, C2-C8 haloalkylcarbonyl, C2-C6 alkoxyalkyl, C2-C6 alkylaminoalkyl, C2-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C4-C 10 Cycloalkylcarbonyl, C5~C 12 Cycloalkylalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-C 10 Dialkylaminocarbonyl, C3-C8 dialkylaminoalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C 10These are trialkylsilyl, C1-C6 alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6 alkylsulfonylamino, phenyl, pyridinyl, or thienyl. Each R 19 These are independently H, cyano, C2-C3 alkylcarbonyl, or C2-C3 haloalkylcarbonyl. Each R 20 These are independently H, C1-C6 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C1-C6 alkoxy or C3-C 10 Trialkylsilyl, or G 1 And, Each u and v is independently 0, 1, or 2, provided that the sum of u and v is 0, 1, or 2. Each p and q is independently 0, 1, or 2, where the sum of u and v is 0, 1, or 2, and when p is 0, q is not 1 or 2.

[0138] Embodiment A42a Each has the following structure [ka] A saturated target, its N-oxide salt and stereoisomer, combined with at least one saturated precursor defined by any one of the following, which is a compound defined in claim 1 of PCT / US2018 / 035015, published as International Publication Brochure No. 2018222646, and is a saturated target, its N-oxide salt and stereoisomer, [ka] (In the formula, Q 1 Q 2 , R 1 , R 7 , R8 , R 9 J, Y, and W, et al., published International Publication No. 201 (Having the meaning defined in claim 1 of PCT / US2018 / 035015, published as brochure 8 / 222646). The text from claim 1 on page 82, line 6 to page 86, line 21 of International Publication brochure 2018 / 222646 is incorporated herein by reference solely for the purpose of defining the structure of this embodiment, and the text is reproduced in Embodiment A42.

[0139] Embodiment A43 An unsaturated precursor defined by one of the following formulas, [ka] (In the formula, Q, W 2 , R 1 , R 2 (Y and Z, etc., have the meanings defined in claim 1 of PCT / EP2018 / 057628, which was published as International Publication Brochure 2018 / 184890). The German text from claim 1, from page 133, line 9 to page 136, line 4 of International Publication Brochure 2018 / 184890, is incorporated herein by reference solely for the purpose of defining the structure of this embodiment.

[0140] Embodiment A43a Each has a structure [ka] A saturated target and salt thereof, combined with at least one unsaturated precursor defined by any one of the following, wherein the saturated target is a compound defined in claim 1 of PCT / EP2018 / 057628, published as International Publication Brochure No. 2018 / 184890, wherein the saturated target and salt thereof [ka] (In the formula, Q, W 2 , R 1 , R2 (Y and Z, etc., have the meanings defined in claim 1 of PCT / EP2018 / 057628, published as International Publication Brochure 2018 / 184890). The German text from claim 1, from page 133, line 9 to page 136, line 4 of International Publication Brochure 2018 / 184890, is incorporated herein by reference solely for the purpose of defining the structure of this embodiment.

[0141] Embodiment A44 One unsaturated precursor and, for example, a salt thereof (in the formula) from any one of embodiments A1 to A16 and A31 to A34. R α is -C(Q α )-CHA, CHA is a chiral carbon-containing group and is exemplified by substituted or unsubstituted cyclic or acyclic amino alcohols, 2-oxazolidone, alcohols, amines, sulfinamide sugars, amino acid derivatives (including amino acids), alkyl, aryl, heterocyclic, naphthyl, aliphatic and aromatic esters, as exemplified by (S)-1-(2-fluorophenyl)ethane-1-amine and (S)-1-phenylethane-1-ol. R β Q α Q β , A β , A α , R μ (and nα have the same meaning as defined in embodiments A1 to A16 and A31 to A34).

[0142] Embodiment A45 Unsaturated precursors and, for example, salts thereof of Embodiment A2 (wherein, R α is -C(Q α )-CHA, and [ka] (That is.) CHA is a chiral carbon-containing group exemplified by substituted or unsubstituted, cyclic or acyclic, amino alcohols, 2-oxazolidone, alcohols, amines, sulfinamide sugars, alkyl, aryl, heterocyclic, naphthyl, aliphatic and aromatic esters. R β Q α Q β , A β , A α , R μ And nα have the same meaning as defined in Embodiment A2.

[0143] Embodiment A46 Unsaturated precursors and, for example, salts thereof of Embodiment A2 (wherein, R α is -C(Q α )-CHA, [ka] CHA is described in Chirality. 2019; 1-37 and in Key Chiral Auxiliary Applications (Second Edition) (ed.: Roos, G.), Academic Press, Boston, 2014. Chiral auxiliaries referenced in ISBN 978-0-12-417034-6, and References in Glorius, F.; Gnas, Y. (2006). "Chiral Auxiliaries - Principles and Recent Applications". Synthesis. 2006(12):1899-1930, and Jamali, Fakhreddin (1993). “Chapter 14:Stereochemically Pure Drugs: An Overview”.In References found in Wainer, Irving W. (ed.). Drug Stereochemistry: Analytical Methods and Pharmacology. Marcel Dekker, Inc. pp. 375-382. Evans, DA; Helmchen, G.; Rueping, M. (2007). “Chiral Auxiliaries in Asymmetric Synthesis”. In Christmann, M (ed.). Asymmetric Sy References within the inthesis - The Essentials. Wiley-VCH Verlag GmbH & Co. pp.3-9, and This is referenced in J.Am.Chem.Soc.97(23):6908-6909, R β Q α Q β , A β , A α , R μ (and nα have the same meaning as defined in Embodiment A2).

[0144] Embodiment A46a Unsaturated precursors and, for example, salts thereof of Embodiment A2 (wherein, R α is -C(Q α )-CHA, [ka] CHA is one of (R)-BINOL, (S)-BINOL, or trans-2-phenylcyclohexanol. [ka] R=R ζ And, R β Q α Q β , A β , A α , R μ , R ζ (and nα have the same meaning as defined in Embodiment A2).

[0145] Embodiment A47 One unsaturated precursor and, for example, a salt thereof (in the formula, Rβ Q α Q β , A β , A α , R μ And nα have the same meaning as defined in Embodiment A2, or the same meaning as defined in any one of Embodiments A1-A16 or A31-A34. R α is -C(Q α )-CHA is, CHA is, Chiral auxiliaries mentioned in Chirality. 2019; 1-37, and Key Chiral Auxiliary Applications (Second Edition) (ed.: Roos, G.), Academic Press, Boston, 2014 ISBN 978-0-12-417034-6, and those referenced in Glorius, F.; Gnas, Y. (2006). "Chiral Auxiliaries - Principles and Recent Applications". Synthesis. 2006(12): 1899-1930, and Jamali, Fakhreddin (1993). “Chapter 14:Stereochemically Pure Drugs: An Overview”.In References found in Wainer, Irving W. (ed.). Drug Stereochemistry: Analytical Methods and Pharmacology. Marcel Dekker, Inc. pp. 375-382. Evans, DA; Helmchen, G.; Rueping, M. (2007). "Chiral Auxiliaries in Asymmetric Synthesis." In Christmann, M (ed.). Asymmetric Synthesis - The Essentials. Wiley-VCH Verlag GmbH & Co. pp. 3-9, as referenced. Referenced in J.Am.Chem.Soc.97(23):6908-6909, and

[0146] Embodiment A47a One unsaturated precursor and, for example, a salt thereof (in the formula, R α is -C(Q α )-CHA, CHA is (R)-BINOL, (S)-BINOL, and trans-2-phenylcyclohexanol. [ka] R is R ζ And, R β Q α Q β , A β , A α , R μ , R ζ (and nα have the same meaning as defined in any one of embodiments A1-A16 or A31-A34).

[0147] Embodiment A48 Unsaturated precursors and, for example, salts thereof of Embodiment A2 (wherein, R α is -C(Q α )-CHA, [ka] CHA is Chiral Q β (R θ )3, Q β H(R θ )2, or Q β H2R θ And R β Q α Q β , A β , A α , R μ (and nα have the same meaning as defined in Embodiment A2).

[0148] Embodiment A49 Unsaturated precursors and, for example, salts thereof of embodiments A1 to A16 and A31 to A34 (wherein, R α is -C(Q α )-CHA, [ka] CHA is Chiral Q β (R θ )3, Q β H(R θ )2, or Q β H2R θ And R β Q α Q β , A β , A α , R μ (and nα have the same meaning as defined in any one of embodiments A1-A16 or A31-A34).

[0149] Embodiment A50 An unsaturated precursor having the following structure. [ka]

[0150] Embodiment B1 A generally described process for preparing a saturated target of formula 1 from an unsaturated precursor of formula 2, [ka] The formula includes Grignard reagents, organolithium reagents, organozinc reagents, and substitutions of 1,4 systems as exemplified by hydrogenation, hydride sources, electron sources (reduction exemplified by Zn / AcOH), or 1,4-addition using enzymes, where, R β , A α , A β , nα, Q α and R ε Each of these has the same meaning as defined in Embodiment A2, R αThis includes H, halogens, or substituted or unsubstituted alkyl, aryl, heterocyclic, naphthyl, esters including aliphatic and aromatic esters exemplified by C(O)OC6H5, -C(O)OC6H4F, amides including aliphatic and aromatic esters exemplified by -C(O)NHC6H5), carbon-containing groups exemplified by hydrazine amides including aliphatic and aromatic esters exemplified by -C(O)NHNHC6H5), thioesters, thionoesters, and, Similar compounds are exemplified by -C(O)NHOC6F5) and -C(S)SC6H5), R α Since it is not bonded to the ring via an O or N atom, for example, R α It is not -OMe, but whenever H is added to the 4th position of the 1,4 system, R α It is not H, R γ H, or a substituted or unsubstituted alkyl, aryl, naphthyl, or other carbon-containing group, R δ The process is characterized by H, or a carbon-containing group such as a substituted or unsubstituted alkyl, aryl, or naphthyl atom.

[0151] Embodiment B1a A saturated target of formula 1 as defined in embodiment B1, which is produced therefrom as an impurity, in combination with an amount of an intermediate unsaturated precursor as defined in any one of embodiments A1 to A52 and B1.

[0152] Embodiment B1b A generally described process for preparing a saturated target of formula 1 from an unsaturated precursor of formula 2, [ka] This includes substitutions of 1,4 systems, exemplified by Grignard reagents, organolithium reagents, organozinc reagents, hydrogenation, hydride sources, electron sources, reduction, Zn / AcOH, or enzymes, R β , A α , A β , nα, Q α and Rε Each of these has the same meaning as defined in Embodiment A2, R α This is a carbon-containing group exemplified by esters containing H, halogens, or substituted or unsubstituted alkyl, aryl, heterocyclic, naphthyl, aliphatic and aromatic esters (e.g., C(O)OC6H5 or -C(O)OC6H4F), amides containing aliphatic and aromatic elements (e.g., -C(O)NHC6H5), hydrazine amides containing aliphatic and aromatic elements (e.g., -C(O)NHNHC6H5), thioesters, thionoesters and similar compounds such as -C(O)NHOC6F5);-C(S)SC6H5). R γ The process involves H or a carbon-containing group such as substituted or unsubstituted alkyl, aryl, or naphthyl. R δ H, or a substituted or unsubstituted alkyl, aryl, naphthyl, or other carbon-containing group, however, R α Since it is not bonded to the ring via an O or N atom, for example, R α It is not -OMe, but whenever H is added to the 4th position of the 1,4 system, A α N(Me) and R β Except when R is m-(trifluoromethyl)benzene, α It is not H, In the case of m-(trifluoromethyl)benzene or 6-(trifluoromethyl)pyridine-3-yl, R α This could be, for example, H in the following scheme: [ka]

[0153] Embodiment B1c A process for preparing a saturated target from a corresponding unsaturated precursor according to any one of the processes exemplified by Embodiments B1 and B1b, etc., comprising combining an unsaturated precursor, a nucleophile exemplified by a Grignard reagent, an organolithium reagent, an organozinc reagent, a hydrogen source, e.g., H2 / Pd / C, or a hydride source, or an electron source exemplified by Zn / AcOH, and at least one solvent to perform a 1,4-system substitution, e.g., a 1,4-addition reaction on the unsaturated precursor, to obtain a saturated target generally defined by the following formula. [ka]

[0154] Preferably, depending on the reaction conditions, one or more isomers, such as a trans isomer or a cis isomer, are present in excess. [ka]

[0155] Embodiment B1d The generally described processes for preparing saturated targets from corresponding unsaturated precursors, including substitution of unsaturated precursor 1,4 systems using Grignard reagents, organolithium reagents, organozinc reagents, and hydrogenation or hydride sources, e.g., 1,4-addition. In these processes, the resulting saturated target product is in excess of one or more possible isomers, and the process is represented by a general scheme selected from the following groups. [ka] [ka]

[0156] Embodiment B2 A process according to any one of the processes exemplified by Embodiments B1 and B1b, etc., comprising combining an unsaturated precursor, a nucleophile exemplified by a Grignard reagent, an organolithium reagent, an organozinc reagent, a hydrogen source, for example H2 / Pd / C or a hydride source or an electron source exemplified by Zn / AcOH, and a solvent to carry out a 1,4-system substitution of the unsaturated precursor, for example a 1,4-addition reaction to obtain a saturated target.

[0157] Embodiment B2a A generally described process for preparing a saturated target of formula 1 from an unsaturated precursor of formula 2, [ka] This includes Grignard reagents, organolithium reagents, organozinc reagents, and substitutions of 1,4 systems exemplified by hydrogenation or 1,4-addition using a hydride source. In this process, the saturated target product has one or more possible isomers, where R α , R β , A α , A β , nα, Q α and R ε Each of these has the same meaning as defined in Embodiment A2, R γ However, H or R α and R δ However, H or R α That is the process.

[0158] Embodiment B3 A process according to either Embodiment B2 or B2a, comprising combining one or more catalytic components selected from an unsaturated precursor, a Grignard reagent, an organolithium reagent, an organozinc reagent, or a hydride source, a solvent, and a catalyst; a pre-catalyst and a co-catalyst, respectively, to perform a 1,4-system substitution of the unsaturated precursor, for example, a 1,4-addition reaction, to obtain a saturated target.

[0159] Embodiment B3a A process according to either Embodiment B2 or B2a, comprising combining an unsaturated precursor, a nucleophile exemplified by a Grignard reagent, an organolithium reagent, an organozinc reagent, or a hydride source, a solvent, and a catalyst; one or more catalytic components selected from a pre-catalyst and a co-catalyst, respectively, to obtain a saturated target by 1,4-series substitution of the unsaturated precursor, exemplified by a 1,4-addition reaction. In this process, the saturated target product has an excess of one or more possible isomers.

[0160] Embodiment B4 A process according to any one of embodiments B2;B2a;B3;B3a, wherein RGA is a reversibly bonded adduct, further comprising in any scheme or any combination thereof an additive which is a source of a reversibly bonded adduct to an unsaturated precursor such as a Lewis acid to provide an improved 1,4-addition reaction to an unsaturated precursor for obtaining a saturated target, [ka] The improvements provided are, To protect some of the unsaturated precursors from undesirable reactions, To increase route selectivity; To increase selectivity for a specific desired isomer; To increase the reactivity of unsaturated precursors; and Required R δ To enable a reduction in the amount of supply source, for example, Grignard reagents. one of the processes (In the formula, R α , R β , R γ , A α , A β , nα, Q α R ε and R δ (This has the same meaning as defined in any one of Embodiments B1; B1a, B1b; B2, and B2a).

[0161] Embodiment B5 A process among embodiments B2; B2a; B3; B3a; and B4, further comprising a step of purifying the obtained saturated target product.

[0162] Embodiment B6 A process according to any one of embodiments B2; B2a; B3; B3a; B4; and B5, further comprising the step of crystallizing the obtained saturated target product.

[0163] Embodiment B6a One of the processes of Embodiments B2;B2a;B3;B3a;B4; and B5, further comprising the step of obtaining an amorphous solid saturated target product by subjecting a saturated target obtained by any one of the processes of Embodiments B2;B2a;B3;B3a;B4 to spray drying, freeze-drying, or the like, or by adsorbing the solution thereof onto a solid support material.

[0164] Embodiment B7 A process any one of embodiments B2 to B6, comprising a 1,4-addition reaction to obtain a saturated target by combining a nucleophile selected from a nucleophile exemplified by an unsaturated precursor, a Grignard reagent, an organolithium reagent, an organozinc reagent, or a hydride source, a solvent; a catalyst; a precatalyst; a cocatalyst, and an additive which is a source of an adduct reversibly bonded to the unsaturated precursor, and further comprising the step of purifying and crystallizing the reaction product to obtain a crystalline purified saturated target product.

[0165] Embodiment B8 The process according to Embodiment B7, wherein the combination step comprises a Grignard reagent; an organolithium reagent; a solvent such as diethyl ether; an organozinc reagent or hydride source having two or more catalytic components selected from a catalyst; a pre-catalyst; a co-catalyst and mixture thereof; and a Lewis acid.

[0166] Embodiment B9 A process in any one of Embodiments B1 to B8, comprising dissolving an unsaturated precursor in a solvent exemplified by diethyl ether, and preferably adding a catalyst; pre-catalyst; co-catalyst, for example, a catalyst component comprising both CuBr.SMe2 (copper(I) bromide dimethyl sulfide complex) and one or more combinations of R-BINAP or (S)-N-((S)-1-(butylamino)-1-oxo-3-phenylpropan-2-yl)-2-(((E)-2-(diphenylphosphanyl)benzylidene)amino)-3-methylbutanamide, [ka] A process comprising, for example, stirring the reaction mixture by stirring or mixing in a continuous reactor, optionally adding a source of reversibly bonded adducts to an unsaturated precursor such as a Lewis acid exemplified by trimethylsilyl chloride, and continuing stirring for an appropriate time exemplified by about 20 minutes; adjusting the temperature to an optimal level, preferably a low temperature such as -20°C to -25°C; adding a nucleophile, such as a Grignard reagent or a hydride source, and stirring for a certain period of time to achieve the optimal product by balancing parameters such as the desired quality and acceptable yield within a reasonable reaction time; quenching the reaction mixture with, for example, an aqueous solution of NH4Cl, and optionally extracting it with a suitable solvent; optionally washing the combined organic layer with, for example, a saturated brine solution, optionally drying it with, for example, Na2SO4, and optionally concentrating it to obtain a saturated target product.

[0167] Embodiment B10 The process according to Embodiment B9, further comprising the step of purifying the obtained saturated target product.

[0168] Embodiment B11 A process according to either Embodiment B9 or B10, further comprising the step of crystallizing the obtained saturated target product.

[0169] Embodiment B12 The process of Embodiment B1, In the first container A, the unsaturated precursor is dissolved in a solvent exemplified by diethyl ether and stirred at an appropriate temperature; optionally, the reaction mixture is cooled to an appropriate temperature such as -20°C to -25°C, a Lewis acid, such as trimethylsilyl chloride, is added, and the mixture is stirred for an appropriate period of time. In the second container B, a catalyst component is introduced that includes one or more of the following: a catalyst; a pre-catalyst; a co-catalyst exemplified by combinations of both CuBr.SMe2 (copper(I) dimethyl sulfide complex); and R-BINAP. [ka] A process comprising: adding a nucleophilic component, such as a Grignard reagent, an organolithium reagent, an organozinc reagent, or a hydride source, to container B at a suitable temperature (preferably low temperature), stirring for a while; adding the contents of container A to container B at a suitable temperature (preferably low temperature) and at a suitable rate, stirring the mass for a suitable time, typically 20 minutes; quenching the reaction mixture in, for example, an aqueous solution of NH4Cl, optionally extracting it with a suitable solvent; optionally washing the combined organic layer with, for example, a saturated brine solution, drying it with, if necessary, Na2SO4, and optionally concentrating it to obtain a saturated target product.

[0170] Embodiment B13 The process of embodiment B12 further includes a step of purifying the obtained saturated target.

[0171] Embodiment B14 A process according to either embodiment B12 or B13, further comprising the step of crystallizing the obtained saturated target product.

[0172] Embodiment B15 The process is one of the embodiments B1 to B14, wherein the unsaturated precursor is one of embodiments A1 to A35 defined above, and includes 1,4-addition using a 1,4-system substitution of the unsaturated precursor, such as a Grignard reagent, organolithium reagent, organozinc reagent, or hydride source.

[0173] Embodiment B15a The use of an unsaturated precursor from any one of the embodiments A1 to A35 defined above as an intermediate in a method for preparing a saturated target as defined in any one of embodiments B1 to B14.

[0174] Embodiment B15b A saturated target as defined in B1, combined with an intermediate unsaturated precursor produced using any one of the methods of Embodiments B1 to B14, as an impurity.

[0175] Embodiment B15c The use of any one of the unsaturated precursors of Embodiment B1 as defined above as an intermediate in a method for preparing a saturated target as defined in any one of Embodiments B1 to B14.

[0176] Embodiment B15d A saturated target as defined in B1, combined with an intermediate unsaturated precursor produced by any one of the methods of Embodiments B1 to B14, as an impurity.

[0177] Embodiment B16 The unsaturated precursor is [ka] A process according to any one of Embodiments B1 to B15, wherein the compound is an embodiment A10 as illustrated by the scheme, The markers that can be formed using the above scheme have the following structure [ka] It can include one, some, or all of them. A process comprising substitution of unsaturated precursor 1,4 systems, such as 1,4-addition, using Grignard reagents or / or organolithium reagents, as exemplified by (3-(trifluoromethyl)phenyl)lithium.

[0178] Embodiment B16a The unsaturated precursor is in the following scheme [ka] A process according to any one of Embodiments B1 to B15, wherein the compound is an embodiment A10 as illustrated by, A process comprising substitution of unsaturated precursors 1,4 systems, such as 1,4-addition, using Grignard reagents exemplified by 3-(trifluoromethyl)phenylmagnesium bromide and 3-(trifluoromethyl)phenyl]magnesium chloride.

[0179] Embodiment B16b The unsaturated precursor is in the following scheme [ka] A process according to any one of Embodiments B1 to B15, wherein the compound is an embodiment A10 as illustrated by, A process comprising substitution of unsaturated precursor 1,4 systems, such as 1,4-addition, using organolithium reagents, exemplified by 3-(trifluoromethyl)phenyllithium.

[0180] Embodiment B16c The unsaturated precursor is the scheme [ka] A process according to any one of Embodiments B1 to B15, wherein the compound is an embodiment A10 as illustrated by, A process comprising substitution of unsaturated precursors 1,4 systems, such as 1,4-addition, using organozinc reagents exemplified by 3-(trifluoromethyl)phenylzinc(II) bromide.

[0181] Embodiment B16d The unsaturated precursor is in the following scheme [ka] A process according to any one of Embodiments B1 to B15, wherein the compound is an embodiment A10 as illustrated by, The markers that can be formed using the above scheme have the following structure [ka] It can include one, some, or all of them. A process comprising substitution of unsaturated precursor 1,4 systems, such as 1,4-addition, using Grignard reagents or / or organolithium reagents, as exemplified by 3-(trifluoromethyl)phenyl)lithium.

[0182] Embodiment B17 The following scheme [ka] A process illustrated by, A process comprising substitution of unsaturated precursors 1,4 systems, such as 1,4-addition, using a Grignard reagent exemplified by 3-(trifluoromethyl)phenylmagnesium bromide.

[0183] Embodiment B18 scheme [ka] A process illustrated by, A process involving 1,4-addition and other substitutions of 1,4 systems using Grignard reagents, exemplified by 3-(trifluoromethyl)phenylmagnesium bromide.

[0184] Embodiment B18a scheme [ka] The process of embodiment B18 as illustrated by Glyni, exemplified by 3-(trifluoromethyl)phenylmagnesium bromide A process involving 1,4-addition and other substitutions of 1,4 systems using Jarl's reagent.

[0185] Embodiment B18b scheme [ka] The process of embodiment B18 as illustrated by A process involving 1,4-addition and other substitutions of the 1,4 system using Grignard reagents, exemplified by [3-(trifluoromethyl)phenyl]magnesium bromide].

[0186] Embodiment B18c The following scheme [ka] A process illustrated by, A process involving substitution of 1,4 systems, such as 1,4-adductive organolithium reagents, exemplified by 3-(trifluoromethyl)phenyllithium.

[0187] Embodiment B18d The following scheme [ka] A process illustrated by, Processes involving substitution of 1,4 systems, such as 1,4-adduct organozinc reagents, exemplified by 3-(trifluoromethylphenylzinc(II) bromide).

[0188] Embodiment B19 The following scheme [ka] A process illustrated by, A process including substitution of the 1,4 system by reduction of the double bond of 1-methyl-2H-pyrrole-5-one, as exemplified by the use of a hydride source.

[0189] Embodiment B19a scheme [ka] The process of embodiment B19 as illustrated by, A process involving 1,4-system substitution by reduction of the double bond in the 1-methyl-2H-pyrrole-5-one group, as exemplified by the use of a hydride source.

[0190] Embodiment B19b The following scheme [ka] A process illustrated by, A process involving 1,4-system substitution by reduction of the double bond in the 1-methyl-2H-pyrrole-5-one group, as exemplified by the use of a hydride source.

[0191] Embodiment B19c The following scheme [ka] A process illustrated by, A process involving 1,4-system substitution by reduction of the double bond in the 1-methyl-2H-pyrrole-5-one group, as exemplified by the use of a hydride source.

[0192] Embodiment B20 scheme [ka] A process represented by, A process involving 1,4-system substitution by reduction of the double bond in the 1-methyl-2H-pyrrole-5-one group, as exemplified by the use of a hydride source.

[0193] Embodiment B21a A process for obtaining a saturated target from an unsaturated precursor represented by the following scheme, [ka] The process includes 1,4-system substitutions such as 1,4-addition using a Grignard reagent or hydride source, and the saturated target is a compound as defined in claim 1 of PCT / US2014 / 068073, which was published as international publication brochure 2015 / 084796, and Q 1 Q 2 , R 1 , R 2 , R 3 , R 4 , R 6 , Y 1 and Y 2 The process, etc., has the meaning defined in claim 1 of PCT / US2014 / 068073, which was published as International Publication No. 2015 / 084796. The text from claim 1, from page 286, line 6 to page 289, line 23 of International Publication No. 2015 / 084796, is incorporated herein by reference specifically for the purpose of defining the structure of this embodiment. The text reproduced in Embodiment A35a.

[0194] Embodiment B21b A process for obtaining a saturated target from an unsaturated precursor represented by the following scheme, [ka] The process includes 1,4-system substitutions such as 1,4-addition using a Grignard reagent or hydride source, and the saturated target is a compound as defined in claim 1 of PCT / US2014 / 068073, which was published as international publication brochure 2015 / 084796, and Q 1 Q 2 , R 1 , R 2 , R 3 , R 4 , R 6 , Y 1 and Y 2The process, etc., has the meaning defined in claim 1 of PCT / US2014 / 068073, which was published as International Publication No. 2015 / 084796. The text from claim 1, from page 286, line 6 to page 289, line 23 of International Publication No. 2015 / 084796, is incorporated herein by reference specifically for the purpose of defining the structure of this embodiment. The text reproduced in Embodiment A35a.

[0195] Embodiment B21c A process for obtaining a saturated target from an unsaturated precursor, [ka] The process includes 1,4-system substitutions such as 1,4-addition using a Grignard reagent or hydride source, and the saturated target is a compound as defined in claim 1 of PCT / US2014 / 068073, which was published as international publication brochure 2015 / 084796, and Q 1 Q 2 , R 1 , R 2 , R 3 , R 4 , R 6 , Y 1 and Y 2 The process, etc., has the meaning defined in claim 1 of PCT / US2014 / 068073, which was published as International Publication No. 2015 / 084796. The text from claim 1, from page 286, line 6 to page 289, line 23 of International Publication No. 2015 / 084796, is incorporated herein by reference specifically for the purpose of defining the structure of this embodiment. The text reproduced in Embodiment A35a.

[0196] Embodiment B22 The following scheme [ka] A process illustrated by, A process involving the substitution of unsaturated precursors 1,4.

[0197] Embodiment B23 The following scheme [ka] A process illustrated by, A process involving the substitution of unsaturated precursors 1,4.

[0198] Embodiment B24 The following scheme [ka] A process illustrated by, A process involving the substitution of unsaturated precursors 1,4.

[0199] Embodiment B25 The following scheme [ka] A process illustrated by, A process involving the substitution of unsaturated precursors 1,4.

[0200] Embodiment B26 The following scheme [ka] A process illustrated by, A process involving the substitution of unsaturated precursors 1,4.

[0201] Embodiment B27a The following scheme [ka] A process illustrated by, A process involving the substitution of unsaturated precursors 1,4.

[0202] Embodiment B27b The following scheme [ka] A process illustrated by, A process involving the substitution of unsaturated precursors 1,4.

[0203] Embodiment B28a scheme [ka] A process illustrated by, Processes involving 1,4-addition and other substitutions of 1,4 systems.

[0204] Embodiment B28b The following scheme [ka] A process illustrated by, A process involving 1,4-addition and other substitutions of 1,4 systems using organolithium reagents, exemplified by 1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yllithium.

[0205] Embodiment B29a The following scheme [ka] A process illustrated by, Processes involving 1,4-addition and other substitutions of 1,4 systems.

[0206] Embodiment B29b The following scheme [ka] A process illustrated by, A process involving the substitution of 1,4 systems, such as 1,4-adductive organolithium reagents exemplified by (6-(trifluoromethyl)pyridine-3-yl)lithium.

[0207] Embodiment B30a The following scheme [ka] A process illustrated by, Processes involving 1,4-addition and other substitutions of 1,4 systems.

[0208] Embodiment B30b The following scheme [ka] A process illustrated by, This includes substitutions of 1,4 systems such as 1,4-addition using organolithium reagents, exemplified by 1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yllithium. Rothes.

[0209] Embodiment B31 A process according to any one of embodiments B1 to B30b, which yields an excess amount of one or more possible isomers.

[0210] Embodiment B32 A process according to any one of embodiments B1 to B30b, which yields an excess amount of anti-isomer.

[0211] Embodiment B33 A process according to any one of embodiments B1 to B30b, which yields an excess amount of syn-isomer.

[0212] Embodiment B34 A process according to any one of Embodiments B1 to B33, wherein one or more of the possible chiral isomers are obtained in excess of the others.

[0213] Embodiment B35 Any one of the processes in Embodiments B1 to B34 yields an excess of chiral anti-isomers.

[0214] Embodiment B36 One of the processes in Embodiments B1 to B34 yields a chiral anti-isomer with an excess S,S configuration.

[0215] Embodiment B37 Magnesium, lithium, zinc, iPrMgCl, iPrMgBr, iPrMgI, hexyllithium, butyllithium, tert-butyllithium, The process according to any one of Embodiments B1 to B36, for preparing reagents for 1,4 system substitution using 4-methylpentyl lithium, isobutyllithium, or a combination thereof, in situ and / or before use in a substitution reaction.

[0216] Embodiment B38 The process according to any one of Embodiments B1 to B36, wherein magnesium halogen exchange or lithium halogen exchange is used for the preparation of reagents for in-situ and / or pre-use 1,4 system substitution.

[0217] Embodiment B39 A process according to any one of embodiments B1 to B38, carried out in the presence of a metal.

[0218] Embodiment B40 The process according to Embodiment B39, wherein the metal is selected from Cu; Ni; Ti; Co; and Fe.

[0219] Embodiment B41 The process according to Embodiment B39, wherein the metal is selected from Cu; Ni; and Ti.

[0220] Embodiment B42 The process according to Embodiment B39, wherein the metal is Cu.

[0221] Embodiment B43 The process according to Embodiment B39, wherein the metal is Ni.

[0222] Embodiment B44 The process according to any one of embodiments B39 to B43, wherein a metal is present in a catalytic amount.

[0223] Embodiment B45 The process according to any one of Embodiments B1 to B44, optionally carried out in the presence of a chiral compound bonded to or part of a solid material or substrate.

[0224] Embodiment B46 The process according to Embodiment B45, wherein the chiral compound is selected from the group comprising naturally occurring, synthetic, modified (e.g., substituted, etc.) amino acids, exemplified by N,N-dimethyl-L-prolinium and L-proline; peptides, exemplified by (S)-N-((S)-1-butylamino-1-oxo-3-phenylpropan-2-yl-2-(E)-2-diphenylphosphanalebenzylideneamino-3-methylbutanamide; phosphorus ligands, exemplified by R-BINAP; proteins; enzymes; and sugars.

[0225] Embodiment B47 The process according to any one of Embodiments B45 to B46, wherein the chiral compound is selected from (S)-N-(S)-1-(butylamino-1-oxo-3-phenylpropane-2-yl-2-(E)-2-diphenylphosphanalebenzylideneamino-3-methylbutanamide).

[0226] Embodiment B48 The process according to any one of embodiments B45 to B47, wherein a chiral compound is present in a catalytic amount.

[0227] Embodiment B49 Lewis base, NH4+Cl - (Ammonium chloride); NH4 + OH - (Ammonium hydroxide); NH3; CN - Ions (e.g., from KCN or NaCN); pyridine; DMA; DMSO; DMF; TEMADA; OH - Ions; pH3; and H2PO3 -A process described in any one of embodiments B45 to B48, which is present in the post-treatment exemplified by ions, etc.

[0228] Embodiment B50 Lewis base in post-processing is NH4 + Cl - (Ammonium chloride); NH4 + OH - (Ammonium hydroxide); NH3; and CN from, for example, KCN or NaCN. - The process described in Embodiment B49, selected from ions. In some cases, the presence of a Lewis base can improve workup and / or increase the yield.

[0229] Embodiment B51 The process according to any one of embodiments B1 to B50, carried out in the presence of a strong base exemplified by MeMgCl;MeMgBr;iPrMgCl;iPrMgBr;BuLi;tert-BuLi;lithium hexyl;NaH;KH, etc. In some cases, the presence of a strong base allows for a reduction in the amount of other components required.

[0230] Embodiment C1a Compounds of formula 3 and, for example, salts thereof. [ka] (In the formula, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. R α , R β , A α , A β , nα and Q α (This has the same meaning as defined in Embodiment A2).

[0231] Embodiment C1b Compounds of formula 3 and, for example, salts thereof. [ka] (In the formula, X α It is a halogen, R α , R β , A α , A β , nα and Q α (This has the same meaning as defined in Embodiment A2).

[0232] Embodiment C1c Compounds of formula 3 and, for example, salts thereof. [ka] (In the formula, X α N(G α )2, N + (O - )(G α )2[that is, N(G α )2 N-oxide], G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. R α , R β , A α , A β , nα and Q α (This has the same meaning as defined in Embodiment A2).

[0233] Embodiment C2 Compounds of formula 3 and, for example, salts thereof. [ka] (In the formula, the compound of formula 3 does not contain a covalent nitrogen-halogen bond.) X α These are halogen, SPh, SePh, and SG α SeG α And, G α R is a phenyl compound substituted with 0 to 5 groups selected from alkyl, haloalkyl, and haloalkyl groups, respectively. α , R β , A α , A β , nα and Q α (This has the same meaning as defined in Embodiment A2).

[0234] Embodiment C2b As an impurity, a saturated target compound of formula 1 combined with an intermediate compound of formula 3 (which is produced thereby), wherein the intermediate is a compound defined in any one of embodiments C1a; C1b; C1c; and C2, and R γ However, a saturated compound of the formula having the same meaning as defined in any one of embodiments B1, B1a, B1b; B2 and B2a. [ka]

[0235] Embodiment C3a Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen; alkyl; and haloalkyl, respectively. [ka] R β Q α Q β , A β , A α , R μ(and nα have the same meaning as defined in Embodiment A2).

[0236] Embodiment C3b Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, X α Halogen, N(G α ) 2, N + (O - )(G α )2, [ka] R β Q α Q β , A β , A α , R μ (and nα have the same meaning as defined in Embodiment A2).

[0237] Embodiment C4a Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, X α SPh, SePh, SG α ,SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen; alkyl; and haloalkyl, respectively. [ka] R β Qα Q β , A β , R π , R μ (and nα have the same meaning as defined in Embodiment A2).

[0238] Embodiment C4b Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, X α Halogen, N(G α )2, N + (O - )(G α )2, [ka] R β Q α Q β , A β , R π , R μ (and nα have the same meaning as defined in Embodiment A2).

[0239] Embodiment C5a Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 1, X α SPh, SePh, SG α SeG α And, G αThis refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R β Q α Q β , A β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0240] Embodiment C5b Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 1, X α It is a halogen, [ka] R β Q α Q β , A β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0241] Embodiment C5c Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 1, X αThese are SPh and SePh, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R β Q α Q β , A β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0242] Embodiment C6a Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R β Q α Q β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0243] Embodiment C6b Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, X α It is a halogen, [ka] R β Q α Q β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0244] Embodiment C7a Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 2, A β It is CH2, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R β Q α Qβ , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0245] Embodiment C7b Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(Q α )Q β R μ And, A α is -N(R π )- and, nα is 2, A β It is CH2, X α It is a halogen, [ka] R β Q α Q β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0246] Embodiment C8a Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)Q β R μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, X α SPh, SePh, SG α SeG α And, G αThis refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R β Q β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0247] Embodiment C8b Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)Q β R μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, X α is, N + (O - )(G α )2, [ka] R β Q β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0248] Embodiment C9a Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, Aβ It is CH2, Q α O is, Q β NH is, X α SPh, SePh, SG α SeG α And, G α These are phenyl groups; alkyl groups; and haloalkyl groups, each substituted with 0 to 5 groups selected from alkyl groups, haloalkyl groups, phenyl groups, and halogens. [ka] R β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0249] Embodiment C9b Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH is, X α These are SPh and SePh, [ka] R β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0250] Embodiment C9c Compounds of Embodiment C2 and, for example, salts thereof (wherein, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH is, X α It is a halogen, [ka] R β , R π and R μ (This has the same meaning as defined in Embodiment A2).

[0251] Embodiment C10 Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R β , R π and R ζ (This has the same meaning as defined in Embodiment A2).

[0252] Embodiment C11 Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from, R β , non-substituted, or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from each of the following. λ And, X α These are SPh and SePh, [ka] R π and R ζ (This has the same meaning as defined in Embodiment A2).

[0253] Embodiment C12 Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ Up to 5 substituents independently selected from each of them A phenyl ring substituted with, R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from each of the following. λ And, X α These are SPh and SePh, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0254] Embodiment C12a Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from each of the following. λ , X α It is a halogen, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0255] Embodiment C12b Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from each of the following. λ , X α is, N + (O - )(G α )2, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0256] Embodiment C13 Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R αis -C(O)NHR μ And, A α It is -NH-, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from each of the following. λ , X α SPh, SePh, SG α SeG α , N + (O - )(G α )2, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0257] Embodiment C14 Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 2, A β It is CH2, Q α O is, Qβ NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to 5 substituents independently selected from λ , X α SPh, SePh, SG α SeG α , N + (O - )(G α )2, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0258] Embodiment C15 Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 2, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β = Non-substitution, or R ζR is a phenyl ring substituted with up to 5 substituents independently selected from each of the following. λ , X α SPh, SePh, SG α SeG α , N + (O - )(G α )2, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0259] Embodiment C16 Any one of the compounds from Embodiments C1 to C15 and, for example, a salt thereof. (In the formula, X α It is an SPh, R α , R β , A α , A β , nα and Q α (This has the same meaning as Embodiment A2).

[0260] Embodiment C16a Any one of the compounds from Embodiments C1 to C15 and, for example, a salt thereof. (In the formula, X α This is N(Me)2, R α , R β , A α , A β , nα and Q α (This has the same meaning as Embodiment A2).

[0261] Embodiment C16b Compounds having the following formula, [ka]

[0262] Embodiment C16c Compounds having the following formula, [ka]

[0263] Embodiment C16d Compounds having the following formula, [ka]

[0264] Embodiment C16e Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compounds, [ka]

[0265] Embodiment C16f Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compounds, [ka]

[0266] Embodiment C16g structure [ka] Compounds for use as pesticides, preferably herbicide synthesis process intermediates and / or marker compounds.

[0267] Embodiment C16h Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compounds, [ka]

[0268] Embodiment C17a Compounds having the following formula, [ka]

[0269] Embodiment C17b Compounds having the following formula, [ka]

[0270] Embodiment C17c Compounds having the following formula, [ka]

[0271] Embodiment C17d Compounds having the following formula, [ka]

[0272] Embodiment C17f Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compounds, [ka]

[0273] Embodiment C17g Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compounds, [ka]

[0274] Embodiment C17h Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compounds, [ka]

[0275] Embodiment C17i Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compounds, [ka]

[0276] Embodiment C18a Compounds having the following formula, [ka]

[0277] Embodiment C18b Compounds having the following formula, [ka]

[0278] Embodiment C19a Compounds having the following formula, [ka]

[0279] Embodiment C19b Compounds having the following formula, [ka]

[0280] Embodiment C20a Compounds having the following formula, [ka]

[0281] Embodiment C20b Compounds having the following formula, [ka]

[0282] Embodiment C21a Compounds having the following formula, [ka]

[0283] Embodiment C21b Compounds having the following formula, [ka]

[0284] Embodiment C22a Compounds having the following formula, [ka]

[0285] Embodiment C22b Compounds having the following formula, [ka]

[0286] Embodiment C23a Compounds having the following formula, [ka]

[0287] Embodiment C23b Compounds having the following formula, [ka]

[0288] Embodiment C24a Compounds having the following formula, [ka]

[0289] Embodiment C24b Compounds having the following formula, [ka]

[0290] Embodiment C25a Compounds having the following formula, [ka]

[0291] Embodiment C25b Compounds having the following formula, [ka]

[0292] Embodiment C26a Compounds having the following formula, [ka]

[0293] Embodiment C26b Compounds having the following formula, [ka]

[0294] Embodiment C27a Compounds having the following formula, [ka]

[0295] Embodiment C27b Compounds having the following formula, [ka]

[0296] Embodiment C28a Compounds having the following formula, [ka]

[0297] Embodiment C28b Compounds having the following formula, [ka]

[0298] Embodiment C29a Compounds having the following formula, [ka]

[0299] Embodiment C29b Compounds having the following formula, [ka]

[0300] Embodiment C30a Compounds having the following formula, [ka]

[0301] Embodiment C30b Compounds having the following formula, [ka]

[0302] Embodiment C31a Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β H is, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R π and R ζ (This has the same meaning as defined in Embodiment A2).

[0303] Embodiment C31b Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π )- and, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β H is H, X α It is a halogen, [ka] R π and R ζ (This has the same meaning as defined in Embodiment A2).

[0304] Embodiment C32a Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β H is, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0305] Embodiment C32b Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 1, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β H is H, X α It is a halogen, [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0306] Embodiment C33 Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 2, A β It is CH2, Q α O is, Q β NH is, R μ is an unsubstituted phenyl ring, or a phenyl ring substituted with up to five substituents independently selected from Rζ. R β H is, X αSPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0307] Embodiment C34 Compounds of Embodiment C2 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 2, A β It is CH2, Q α O is, Q β NH is, R μ is either non-substitutive or R ζ A phenyl ring substituted with up to 5 substituents independently selected from each of the following: R β H is, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [ka] R ζ (This has the same meaning as defined in Embodiment A2).

[0308] Embodiment C35a A compound defined by one of the following structures, [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 3 , R 4 (R6, Y1 and Y2, etc., have the meanings defined in claim 1 of PCT / US2014 / 068073, which was published as International Publication No. 2015 / 084796). The text extracted from claim 1, from page 286, line 6 to page 289, line 23 of International Publication No. 2015 / 084796, is incorporated specifically by reference solely for the purpose of defining the structure of this embodiment, and the text is reproduced in Embodiment A35a. During the ceremony, X α =SPh, SePh, SG α SeG α G α = A phenyl group substituted with 0 to 5 groups selected from alkyl groups, haloalkyl groups, phenyl groups, and halogens; alkyl groups; and haloalkyl groups.

[0309] Embodiment C35b The following formula [ka] Combined with at least one compound defined by any one of the following, Saturated target compound having the following structure [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 3 , R 4(R6, Y1 and Y2, etc., have the meanings defined in claim 1 of PCT / US2014 / 068073, which was published as International Publication No. 2015 / 084796). The text extracted from claim 1, from page 286, line 6 to page 289, line 23 of International Publication No. 2015 / 084796, is incorporated specifically by reference solely for the purpose of defining the structure of this embodiment, and this text is reproduced in Embodiment A35a. Also, during the ceremony, X α =SPh, SePh, SG α SeG α . G α = A phenyl group substituted with 0 to 5 groups selected from alkyl groups, haloalkyl groups, phenyl groups, and halogens; alkyl groups; and haloalkyl groups.

[0310] Embodiment C36a A compound defined by one of the following structures, [ka] (In the formula, Q, R 1 (where Y and W have the meanings defined in claim 1 of PCT / US2020 / 034232, published as International Publication Brochure 2020 / 242946). The text from claim 1 on page 87, line 3 to page 88, line 6 of International Publication Brochure 2020 / 242946 is incorporated herein by reference solely for the purpose of defining the structure of this embodiment, and the text is reproduced in Embodiment A36a, in which, X α =SPh, SePh, SG α SeG α , and G α =alkyl, haloalkyl, and phenyl are phenyl molecules substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0311] Embodiment C36b The following formula [ka] A structure that combines with at least one compound defined by any one of the following [ka] A saturated target compound having, (In the formula, Q, R 1 , R 6 (Y and W, etc., have the meanings defined in claim 1 of PCT / US2020 / 034232, published as International Publication Brochure 2020 / 242946). The text from claim 1 on page 87, line 3 to page 88, line 6 of International Publication Brochure 2020 / 242946 is incorporated herein by reference specifically for the purpose of defining the structure of this embodiment as reproduced in Embodiment A36a, where X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0312] Embodiment C37a A compound defined by one of the following formulas, [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 7 (Y, A, and J, etc., have the meanings defined in Claim 1 of PCT / US2016 / 030450, published as International Publication Brochure 2016 / 182780). The text of Claim 1, from page 101, line 3 to page 106, line 28 of International Publication Brochure 2016 / 182780, is incorporated specifically by reference solely for the purpose of defining the structure of this embodiment, and this text is reproduced in Embodiment A37a. X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0313] Embodiment C37b Compounds for use as pesticides, preferably herbicide synthesis process intermediates and / or markers having any one of the following structures, [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 7 (Y, A, and J, etc., have the meanings defined in Claim 1 of PCT / US2016 / 030450, published as International Publication Brochure 2016 / 182780). The text of Claim 1, from page 101, line 3 to page 106, line 28 of International Publication Brochure 2016 / 182780, is incorporated specifically by reference solely for the purpose of defining the structure of this embodiment, and this text is reproduced in Embodiment A37a. X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0314] Embodiment C37c The following structure [ka] Combined with at least one compound defined by any one of the following, Saturated target compound having the following structure [ka] (In the formula, Q 1 Q 2 , R 1 , R 2 , R 7 Y, A, and J have the meanings defined in Claim 1 of PCT / US2016 / 030450, published as International Publication Brochure 2016 / 182780). The text of Claim 1, from page 101, line 3 to page 106, line 28 of International Publication Brochure 2016 / 182780, is incorporated specifically by reference solely for the purpose of defining the structure of this embodiment, and this text is reproduced in Embodiment A37a, in which, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0315] Embodiment C38 A compound defined by one of the following formulas, [ka] (In the formula, Q 1 Q 2 , R B1 (and X has the meaning defined in claim 1 of PCT / EP2020 / 052780, published as International Publication Brochure 2020 / 161147). The text from claim 1 on page 74, line 10 to page 75, line 10 of International Publication Brochure 2020 / 161147 is incorporated by reference solely for the purpose of defining the three structures of this embodiment, and the text is reproduced in Embodiment A38. During the ceremony, X α SPh, SePh, SG α SeG α And, Gα These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0316] Embodiment C38a The following structure [ka] A saturated target compound of the following formula as defined in claim 1(B) of PCT / EP2020 / 052780, published as international publication brochure No. 2020 / 161147, combined with at least one compound defined by any one of the following: [ka] (In the formula, Q 1 Q 2 , R B1 (and X etc. have the meanings defined in claim 1 of PCT / EP2020 / 052780 specification, which was published as International Publication No. 2020 / 161147). The text from claim 1 on page 74, line 10 to page 75, line 10 of International Publication No. 2020 / 161147 is incorporated specifically by reference solely for the purpose of defining the structure of this embodiment, and the text is reproduced in Embodiment A38, in formula, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0317] Embodiment C39 A compound defined by one of the following formulas, [ka] (In the formula, Q, W 2 , R 1(Y and Z, etc., have the meanings defined in claim 1 of PCT / EP2018 / 069001, which was published as International Publication Brochure No. 2019 / 025156). The German text from claim 1 on pages 109, line 3 to 112, line 6 of International Publication Brochure No. 2019 / 025156 is incorporated by reference specifically for the purpose of defining the structure of this embodiment. Also, during the ceremony, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0318] Embodiment C40 A compound defined by one of the following formulas, [ka] (In the formula, Q 1 Q 2 , R 1 , R 7 , R 9 , J, L, Y and Y 2 (These terms have the meanings defined in claim 1 of PCT / US2018 / 035017, which was published as International Publication Brochure 2018 / 222647). The text from claim 1 on page 84, line 5 to page 89, line 27 of International Publication Brochure 2018 / 222647 is incorporated by reference solely for the purpose of defining the structure of this embodiment, and the text is reproduced in Embodiment A41, in which, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0319] Embodiment C41 Each has the following structure [ka] A saturated target, N-oxide and salt thereof of the following formula, as defined in claim 1 of PCT / US2018 / 035017, published as international publication brochure 2018 / 222647, combined with at least one compound defined by any one of the following: [ka] During the ceremony, Q 1 Q 2 , R 1 , R 7 , R 9 , J, L, Y and Y 2 These terms have the meanings defined in claim 1 of PCT / US2018 / 035017, which was published as International Publication No. 2018 / 222647, and the text from claim 1 on page 84, line 5 to page 89, line 27 of International Publication No. 2018 / 222647 is incorporated by reference specifically for the sole purpose of defining the structure of this embodiment, and the text is reproduced in Embodiment A41. X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0320] Embodiment C42 A compound defined by one of the following formulas, [ka] (In the formula, Q 1 Q 2 , R 1 , R 7 , R 8 , R 9(J, Y, and W, etc., have the meanings defined in claim 1 of PCT / US2018 / 035015, which was published as International Publication Brochure 2018 / 222646). The text of claim 1 from page 82, line 6 to page 86, line 21 of International Publication Brochure 2018 / 222646 is incorporated by reference specifically for the sole purpose of defining the structure of this embodiment. Also, during the ceremony, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl, respectively; halogen group; alkyl group; and This is a phenyl molecule substituted with 0 to 5 groups selected from haloalkyl groups.

[0321] Embodiment C42a Each has the following structure [ka] A saturated target, its N-oxide salt and stereoisomer, combined with at least one compound defined by any one of the following, having the formula below, is a compound as defined in claim 1 of PCT / US2018 / 035015, published as international publication brochure 2018 / 222646, [ka] (In the formula, Q 1 Q 2 , R 1 , R 7 , R 8 , R 9(J, Y and W, etc., have the meanings defined in claim 1 of PCT / US2018 / 035015, which was published as International Publication Brochure 2018 / 222646). The text from claim 1 on page 82, line 6 to page 86, line 21 of International Publication Brochure 2018 / 222646 is incorporated herein by reference solely for the purpose of defining the structure of this embodiment, and the text is reproduced in Embodiment A42. X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0322] Embodiment C43 formula [ka] Compounds defined by any one of the following: (In the formula, Q, W 2 , R 1 , R 2 (Y and Z, etc., have the meanings defined in claim 1 of PCT / EP2018 / 057628, published as International Publication Brochure 2018 / 184890). The text from claim 1 on page 133, line 9 to page 136, line 4 of International Publication Brochure 2018 / 184890 is incorporated herein by reference solely for the purpose of defining the structure of this embodiment. Also, during the ceremony, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0323] Embodiment C43a The following structure [ka] A saturated target and a salt thereof, which is a compound as defined in claim 1 of PCT / EP2018 / 057628, published as international publication brochure 2018 / 184890, combined with at least one compound defined by any one of the above, [ka] (In the formula, Q, W 2 , R 1 , R 2 (Y and Z, etc., have the meanings defined in claim 1 of PCT / EP2018 / 057628, published as International Publication No. 2018 / 184890). The German text from claim 1 on page 133, line 9 to page 136, line 4 of International Publication No. 2018 / 184890 is incorporated herein by reference solely for the purpose of defining the structure of this embodiment, in the formula, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.

[0324] Embodiment D1a The generally described above process for preparing an unsaturated precursor of formula 2 from a compound of formula 3, [ka] A process (wherein X) comprising the oxidation of the corresponding compound of formula 3 using an oxidizing agent such as meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2). α , R α , R β , A α , A β , nα, and Qα Each of these has the same meaning as in Embodiment C1a. This process is X α It is preferable when the substance is a thioether or a selenoether.

[0325] Embodiment D1b The generally described above process for preparing an unsaturated precursor of formula 2 from a compound of formula 3, [ka] A process (wherein X) that includes an elimination reaction using an activator such as a base or Lewis acid. α , R α , R β , A α , A β , nα and Q α Each of these has the same meaning as in Embodiment C1a).

[0326] Embodiment D2a The process of Embodiment D1a comprises dissolving the compound of Formula 3 in a suitable solvent, such as acetic acid; stirring (e.g., by stirring) for a period exemplified by about 20 minutes; and gradually adding an oxidizing agent, such as meta-chloroperoxybenzoic acid (mCPBA), or hydrogen peroxide (H2O2), at a suitable temperature. The reaction mixture is then stirred for a period of time at substantially the same temperature, for example, about 2 hours. The reaction mixture can be quenched, for example, in an aqueous solution of NaHCO3 and extracted typically twice with a suitable solvent. The combined organic layers can be concentrated to obtain the corresponding unsaturated precursor of Formula 2.

[0327] Embodiment D2b The process according to Embodiment D1a comprises dissolving the compound of Formula 3 in a suitable solvent, such as chlorobenzene, stirring for a time exemplified by about 20 minutes (e.g., by stirring), and gradually adding an activator exemplified by a base or Lewis acid at a suitable temperature. The reaction mixture is then stirred for a while at substantially the same temperature, for example, about 2 hours. The reaction mixture can be quenched in, for example, an NH4Cl solution and extracted typically twice with a suitable solvent. The combined organic layers can be concentrated to obtain the corresponding unsaturated precursor of Formula 2.

[0328] Embodiment D3a The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0329] Embodiment D3b The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor, [ka] A process involving the oxidation of compounds.

[0330] Embodiment D3c The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0331] Embodiment D4a The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0332] Embodiment D4b The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0333] Embodiment D5a The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0334] Embodiment D5b The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0335] Embodiment D6a scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0336] Embodiment D6b The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0337] Embodiment D7a scheme [ka] Processes exemplified by the method, using oxidizing agents exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), corresponding to the unsaturated pre- The following formula is used to obtain the precursor compound: [ka] A process involving the oxidation of compounds.

[0338] Embodiment D7b The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0339] Embodiment D8a The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0340] Embodiment D8b The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0341] Embodiment D9a The following scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0342] Embodiment D9b scheme [ka] A process exemplified by the following formula, using an oxidizing agent exemplified by meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H2O2), to obtain the corresponding unsaturated precursor compound, [ka] A process involving the oxidation of compounds.

[0343] Embodiment E1 Compounds of formula 4 and, for example, salts thereof, for use as intermediates in the method for preparing the corresponding saturated target of formula 1, [ka] [ka] (In the formula, R α , R β , A α , A β , nα and Q α R has the same meaning as defined in Embodiment A2, δ and R γ (This has the same meaning as defined in Embodiment B1).

[0344] Embodiment E2 As an impurity, a saturated target compound combined with the intermediate compound of formula 4 defined in embodiment E1, which is generated therethrough.

[0345] Embodiment F1a A process for preparing the compound of formula 3 from the compound of formula 4, as generally described above, [ka] X obtained by using bases and electrophiles α Includes the addition of a "leaving" group, X α , R α , R β , A α , A β , nα and Qα Each of these represents a process that has the same meaning as embodiment C1a. This process is R β It is preferable when H.

[0346] Embodiment F1b A generally described process for preparing a compound of formula 3 from a compound of formula 4, [ka] X is obtained by using a leaving group source such as a halogenating reagent. α Including the addition of a leaving group, X α , R α , R β , A α , A β , nα and Q α A process in which each of the following has the same meaning as embodiment C1a.

[0347] Embodiment F1c A generally described process for preparing a compound of formula 3 from a compound of formula 4, [ka] By utilizing bases and electrophiles, X α Including the addition of a base, X α , R α , R β , A α , A β , nα and Q α A process in which each of the following has the same meaning as embodiment C1b. This process is R β It is preferable when H.

[0348] Embodiment F2a The process of Embodiment F1a comprises dissolving the compound of Formula 4 in a suitable solvent containing a base such as sodium hydride at a specified temperature for a time typically exemplified by cooling and stirring (e.g., stirring) for about 20 minutes; adding an electrophile exemplified by diphenyl disulfide; phenyl hypochlorite; or phenyl hypobromite, dissolved in a suitable solvent at substantially the same temperature; and stirring the reaction mixture for a period of time at substantially the same temperature. The reaction mixture can be quenched, for example, in an NH4Cl solution, extracted typically two or more times with a suitable solvent, the combined organic layer washed, dried over Na2SO4, and concentrated to obtain the corresponding compound of Formula 3. This process is R β It is preferable when H.

[0349] Embodiment F2b The process of Embodiment F1b comprises dissolving the compound of Formula 4 together with a leaving group exemplified by a halogenating reagent (e.g., a bromine source) in a suitable solvent at a specific temperature, and optionally adding a base and / or a catalyst (catalytic components including one or more of a catalyst; pre-catalyst; or co-catalyst). The reaction mixture is stirred (e.g., by stirring) at substantially the same temperature for about 2 hours, the reaction mixture is quenched, and extracted with a suitable solvent. Preferably, the mixture is washed again, and / or the combined organic layers are washed, and optionally dried over, for example, Na2SO4, and concentrated to obtain the corresponding compound of Formula 3.

[0350] Embodiment F3 A process in either embodiment F2a or F2b, further comprising purifying the compound of formula 3 obtained from the above process.

[0351] Embodiment F4 A process according to any one of Embodiments F1 to F3, using either diphenyl disulfide or phenyl hypochlorite as the electrophile.

[0352] Embodiment G1 A storage marker having the following structure, and, for example, a salt thereof, [ka] (In the formula, R β Q α Q β and R π (This has the same meaning as defined in Embodiment A2).

[0353] Embodiment G2 A conserved marker compound of formula D obtained by exposing tetoflupyrrolimeth to sunlight. [ka]

[0354] Embodiment DD1 Conservation marker compounds of the following formula, [ka] (In the formula, R β Q α , A β , A α (and nα have the same meaning as defined in Embodiment A2).

[0355] Embodiment DD2 Conservation marker compounds of the following formula, [ka] (In the formula, R β Q α , A β , and R π (This has the same meaning as defined in Embodiment A2).

[0356] Embodiment DD3 Conservation marker compounds of the following formula, [ka] (In the formula, R π and R ζ (This has the same meaning as defined in Embodiment A2).

[0357] Embodiment DD4 Conservation marker compounds of the following formula, [ka] (In the formula, R β Q α , A β , and R π (This has the same meaning as defined in Embodiment A2).

[0358] Embodiment DD5 Conservation marker compounds of the following formula, [ka] (In the formula, each R ζ (This has the same meaning as defined in Embodiment A2).

[0359] Embodiment DD6 A conserved marker compound according to the following formula. [ka]

[0360] Embodiment DD7 A conserved marker compound according to the following formula. [ka]

[0361] Embodiment DD8 A conserved marker compound according to the following formula. [ka]

[0362] Embodiment DD9 A conserved marker compound according to the following formula. [ka]

[0363] Embodiment DD10 A conserved marker compound according to the following formula. [ka]

[0364] Embodiment DD11 A conserved marker compound according to the following formula. [ka]

[0365] Embodiment H1 A process for preparing a storage marker compound from a corresponding saturated target compound in the following general scheme, wherein the saturated target is exposed to sunlight for a sufficient time to form a detectable amount of the corresponding storage marker when measured by analytical methods exemplified by HPLC and particularly HPLC-MS. [ka] (In the formula, R β , A β , A α , R ζ (and nα have the same meaning as defined in Embodiment A2).

[0366] Embodiment H2 In the following general scheme, a process for preparing a conserved marker compound from a corresponding saturated target compound, [ka] A process comprising exposing a saturated target composition (such as a solution) to sunlight for a sufficient time to form a detectable amount, particularly an amount exceeding the limit of quantification, of the corresponding storage marker in the composition, using analytical techniques exemplified by HPLC-MS.

[0367] Embodiment H2a The following scheme is a process for preparing a corresponding conserved marker compound from a saturated target compound which is (3S,4S)-2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide, [ka] A process comprising exposing a composition (solution, etc.) of (3S,4S)-2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide to sunlight for a time sufficient to form a detectable amount, particularly an amount exceeding the limit of quantification, of the corresponding storage marker in the composition, using analytical techniques exemplified by HPLC-MS.

[0368] Embodiment H3 The process according to either Embodiment H2 or H2a, comprising a solution, particularly an aqueous solution, which is preferably maintained at a predetermined level of acidity / basicity of pH by a method exemplified by preferably including a suitable buffer in an aqueous solution.

[0369] Embodiment H4 The process of Embodiment H3, wherein a saturated target solution is maintained at acidity / basicity levels exemplified by the aqueous solution of the saturated target having a pH selected from about 4±1;7±1; and 10±1, preferably by including a suitable buffer solution of an effective concentration in the aqueous solution.

[0370] Embodiment H5 One of the processes in Embodiments H2; H2a; H3; and H4, wherein the rate at which a corresponding preservation marker is formed from a saturated target compound upon exposure to sunlight is further mediated by a selection of the acidity / basicity of the composition containing the saturated target.

[0371] Embodiment H6 A process according to any one of embodiments H3, H4, and H5, wherein the composition is an aqueous solution, and the rate at which a corresponding storage marker is formed from a saturated target upon exposure to sunlight is mediated by the selection of the pH of the aqueous solution of the saturated target.

[0372] Embodiment H7 A process for minimizing the conversion rate of 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide in a composition to a corresponding storage marker, comprising minimizing and / or avoiding exposure of the composition to sunlight, and / or mitigating the conversion effect of such exposure to sunlight.

[0373] Embodiment H8 A process for minimizing the conversion rate of tetoflupyrrolimeth in a composition to a corresponding storage marker, comprising minimizing the time and extent of exposure of the composition to sunlight, and / or mitigating the conversion effect of such exposure to sunlight.

[0374] Embodiment H9 A process for minimizing the conversion rate of tetoflupyrrolimeth in a composition to a corresponding storage marker, comprising including in the composition a component; an excipient; an adjuvant; a carrier; or any additive that can mitigate at least one of the conversion effects of exposure to sunlight, or that can reduce the rate at which such conversion occurs upon exposure to sunlight in the absence of such component, excipient, adjuvant, carrier, or additive, .

[0375] Embodiment H10 A process for minimizing the conversion rate of tetoflupyrrolimeth in a product containing a tetoflupyrrolimeth composition (including a solution thereof) to a corresponding preservation marker during the manufacturing, packaging, labeling, transport and storage of the product, comprising mitigating or overcoming the effects of exposure to sunlight of the product by including the composition in lightfast, preferably substantially opaque packaging and / or containers (e.g., container-closure systems) that protect the contents from the conversion effects of sunlight by specific properties of the materials comprising them, including by lightfast or opaque coating, or by the use of secondary packaging, or by including any coating applied thereto, including transparent, colorless, or translucent containers that have been made lightfast in amber containers, wherein lightfastness and opacity are related to the wavelength of light that mediates the conversion of tetoflupyrrolimeth to a corresponding preservation marker.

[0376] Embodiment H11 A process and / or composition according to any one of Embodiments H1 to H10, wherein a saturated target compound, preferably tetoflupyrrolimeth, is present in a liquid, solution, emulsion, or suspension composition.

[0377] Embodiment H12 A process for minimizing the rate at which an aqueous solution of tetoflupyrrolimeth is converted to a corresponding storage marker compound when the solution is exposed to sunlight, the process comprising maintaining the pH of the aqueous solution in the range of about 6 to about 8, preferably about 7.

[0378] Embodiment H13 A process for determining the period during which a storage composition containing a saturated target compound, particularly a tetoflupyrrolimeth composition, has been exposed to sunlight during storage, comprising: measuring and quantifying the relative content of a corresponding storage marker compound compared to the content of a saturated target in the composition; and evaluating the period of exposure to sunlight by referring to a standard calibration conversion rate in one or more reference compositions containing a saturated target compound.

[0379] Embodiment H14 The process according to Embodiment H13, wherein the measurement and quantification of the relative content is exemplified by calculating the ratio of the respective areas under the decomposed characterizing peaks of each compound in the test sample by appropriate HPLC analysis.

[0380] Embodiment H15 A process in which the standard calibration rate is determined for a reference composition having the same acidity / basicity as the stored test composition, in any one of Embodiments H13 and H14.

[0381] Embodiment H16 A process in any one of Embodiments H13, H14, and H15, wherein the standard calibration rate is determined relative to a reference composition packaged in the same container system as the stored test composition.

[0382] Embodiment I1 A preservation packaging composition comprising a combination of a detectable amount of a preservation marker compound and the corresponding saturated target compound to which it is converted, as illustrated by the process of Embodiment H2.

[0383] Embodiment I2 In particular, the following formula [ka] The following formulas, including any isomer or enantiomer thereof, are exemplified by (3S,4S)-2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide. [ka] Combined with the saturated target compound, the following formula [ka] A preservation packaging composition of Embodiment I1 comprising a detectable, preferably measurable, amount of a preservation marker compound.

[0384] Embodiment I3 A preservation packaging composition according to any one of Embodiments I1 and I2, comprising a saturated target solution, particularly an aqueous solution, maintained at a predetermined level of acidity / basicity, preferably pH, by a method exemplified by preferably including a suitable buffer system in the aqueous solution.

[0385] Embodiment I4 The preservation packaging composition according to Embodiment I3, wherein the saturated target solution is maintained at an acidity / basicity level exemplified by the saturated target aqueous solution having a pH selected from about 4±1; about 7±1; and about 10±1, by preferably including a suitable buffer in an aqueous solution at a concentration effective for maintaining the acidity / basicity level.

[0386] Embodiment I5 Conservation marker compounds, especially those with the following formula [ka] The compound, upon exposure to sunlight during storage, is released from the corresponding saturated target, particularly according to the following formula. [ka] A storage packaging composition according to any one of Embodiments I1 to I4, wherein the rate of formation from the compound is further mediated by the selection of the acidity / basicity of the saturated target composition over the storage period.

[0387] Embodiment I6 A packaged aqueous composition of tetoflupyrrolimeth, wherein tetoflupyrrolimeth contains any isomer, enantiomer, or mixture thereof when the composition is exposed to sunlight during storage, the following formula [ka] A packaged aqueous composition of tetoflupyrrolimeth, characterized in that the rate at which it is converted to the corresponding storage marker is minimized, and the composition is adapted to maintain a pH in the range of about 6 to about 8, preferably about 7, during storage by including components, excipients, or other components exemplified by a buffer or buffering system in the composition.

[0388] Embodiment I7 An agricultural product comprising a composition of 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide, particularly tetoflupyrrolimeth, comprising any isomer, enantiomer, or mixture thereof that occurs during storage, the following formula [ka] An agricultural product in which the rate of conversion of to the corresponding storage marker is minimized, and the product is adapted to limit, reduce, minimize, or substantially avoid the time and extent to which the composition in the product is exposed to sunlight during storage, and such minimization is compared to an agricultural tetoflupyrrolimeth product without such adaptation.

[0389] Embodiment I8 During the manufacture, packaging, labeling, transport, or storage of the tetoflupyrrolimeth composition, the following formula may be present: [ka] An agricultural product comprising the composition, which is protected to a detectable degree against light-mediated conversion to a corresponding preservation marker compound, wherein the product is light-resistant by certain properties of the materials constituting the composition, by an opaque cover, by the use of secondary packaging, or in an amber container. An agricultural product comprising the composition, which is contained in a substantially lightfast, preferably opaque, packaging and / or container-closure system that protects the contents from the effects of sunlight, including a transparent, colorless or translucent container, and any coating applied thereto, and / or is light-shielded.

[0390] Embodiment I9 The following formula [ka] A tetoflupyrrolimeth composition characterized by a minimized proportion or degree of the photocatalytic conversion of tetoflupyrrolimeth to a corresponding storage marker, comprising at least one component, excipient, adjuvant, carrier or additive that can reduce the conversion effect of exposure to sunlight, or that can reduce the rate at which such conversion occurs upon exposure to sunlight in the absence of such component, excipient, adjuvant, carrier or additive.

[0391] Embodiment I10 A tetoflupyrrolimeth composition that is stabilized to at least a measurable degree against photocatalytic conversion to a corresponding preservation marker during manufacturing, packaging, labeling, transport and storage, characterized in that the composition comprises at least one component, excipient, adjuvant, carrier or additive that can reduce the conversion effect of exposure to sunlight and / or reduce the rate at which such conversion occurs without the component, excipient, adjuvant, carrier or additive.

[0392] Embodiment I11 A product comprising a tetoflupyrrolimeth composition that is shielded from sunlight-mediated conversion to a corresponding preservation marker during any of the following: manufacture; packaging; labeling; transport; or storage of the composition, characterized in that the product comprises the tetoflupyrrolimeth composition contained in substantially lightfast, preferably opaque, packaging, as substantially detailed in Embodiment H10.

[0393] Embodiment I12 A tetoflupyrrolimeth composition that is at least measurably stabilized for conversion to a corresponding preservation marker, or exhibits a measurably reduced conversion rate to a corresponding preservation marker during manufacturing, packaging, labeling, transport and storage, wherein the composition exhibits a standard calibration conversion rate compared to one or more reference compositions containing tetoflupyrrolimeth. a) A buffer solution that maintains the pH of the composition at 7±1; b) UV absorbers; c) Components exhibiting substantially the same absorption spectrum as tetoflupyrrolimeth, as exemplified by suitable dyes, colorants, or pigments; d) Components, etc., that can reduce the amount of sunlight hitting the material; e) Milking agents; f) Reflective pigments such as titanium dioxide; g) A photoprotective coating covering at least a portion of the tetoflupyrrolimeth in the composition; h) A tetoflupyrrolimeth composition comprising at least one component which is any, some, or all of the following: a complex of tetoflupyrrolimeth with a complexing agent, for example, one exemplified by an inclusion complex with a cyclodextrin; the reference composition comprising tetoflupyrrolimeth without the component.

[0394] f Embodiment I14 A buffered tetoflupyrrolimeth composition containing less than a measurable amount, preferably less than a detectable amount, of the corresponding storage marker compound after being stored in a sunlight environment for a period equal to or longer than two months.

[0395] Embodiment I15 A product and / or composition of any one of Embodiments I1 to I12, wherein the saturated target is preferably tetoflupyrrolimeth in a liquid, solution, emulsion, or suspension composition.

[0396] Embodiment J1 Crystalline polymorph I of N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide exhibits at least one of the following properties: The infrared spectrum is essentially shown in Figure 9. The powder X-ray diffraction pattern is essentially as shown in Figure 5. Powder X-ray diffraction pattern with a differential peak at 9.6 at 2θ(±0.20), A powder X-ray diffraction pattern having at least four characteristic peaks represented by 2θ(±0.20) at 9.6, 15.0, 17.3, 17.9, 21.6, and 24.6.

[0397] Embodiment J2 Crystalline polymorph I of tetoflupyrrolimeth exhibits at least one of the following properties: The infrared spectrum is essentially shown in Figure 9. The powder X-ray diffraction pattern is essentially as shown in Figure 5. Powder X-ray diffraction pattern with a differential peak at 9.6 at 2θ(±0.20), A powder X-ray diffraction pattern having at least four characteristic peaks represented by 2θ(±0.20) at 9.6, 15.0, 17.3, 17.9, 21.6, and 24.6.

[0398] Embodiment J3 A composition comprising tetoflupyrrolimeth in crystalline polymorph I as defined in either Embodiment J1 or J2.

[0399] Embodiment J4 A pesticide composition, preferably a herbicidal composition, comprising one crystalline polymorph I from either Embodiment J1 or J2, and a herbicidally acceptable diluent or carrier.

[0400] Embodiment J5 A pesticide composition, preferably a herbicidal composition, prepared from any one of the crystalline polymorph I forms of Embodiments J1 and J2.

[0401] Embodiment K1 Crystalline polymorph II of N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide exhibiting at least one of the following properties: The infrared (IR) absorption spectrum is essentially shown in Figure 10. An infrared (IR) absorption spectrum having at least one characteristic peak selected from values ​​expressed as cm⁻¹ (±1 cm⁻¹) at 1678, 1546, 1395, 946, 924, 885, 825, and 662. The powder X-ray diffraction pattern is essentially as shown in Figure 6. Powder X-ray diffraction pattern having a differential peak represented by 2θ(±0.20) at 6.9, The following: Powder X-ray diffraction pattern having at least four characteristic peaks represented by 2θ(±0.20) selected from the values ​​of 6.9, 11.2, 17.7, 23.5, and 26.3.

[0402] Embodiment K2 Crystalline polymorph II of tetoflupyrrolimeth exhibits at least one of the following properties: The infrared (IR) absorption spectrum is essentially shown in Figure 10. An infrared (IR) absorption spectrum having at least one characteristic peak selected from values ​​expressed as cm⁻¹ (±1 cm⁻¹) at 1678, 1546, 1395, 946, 924, 885, 825, and 662. The powder X-ray diffraction pattern is essentially as shown in Figure 6. Powder X-ray diffraction pattern having a differential peak represented by 2θ(±0.20) at 6.9, The following: Powder X-ray diffraction pattern having at least four characteristic peaks represented by 2θ(±0.20) selected from the values ​​of 6.9, 11.2, 17.7, 23.5, and 26.3.

[0403] Embodiment K3 A composition comprising crystalline polymorph II as described in either Embodiment K1 or K2.

[0404] Embodiment K4 A pesticide composition comprising crystalline polymorph II according to any one of Embodiments K1 and K2, preferably comprising a herbicidal composition and a diluent or carrier that is pesticide-, preferably herbicide-acceptable.

[0405] Embodiment K5 A pesticide composition, preferably a herbicidal composition, prepared from crystalline polymorph II as described in either Embodiment K1 or K2.

[0406] Embodiment K6 A crystallization method for preparing crystalline polymorph I according to either Embodiment J1 or J2, comprising recrystallization from tert-butylmethyl ether.

[0407] Embodiment K6a A method for preparing one of the crystalline polymorph I of embodiments J1 and J2, 1. Dissolve (3R,4S)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylic acid in acetonitrile (200 mL), 2.2-Fluoroaniline and N-methylimidazole are added, 3. Mix the obtained contents at ambient temperature for a period of time exemplified by 10 minutes. 4. Adding chloro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate, 5. Stir the resulting mixture at ambient temperature for a period of time exemplified by 10 hours. 6. For example, removing the solvent by evaporation, 7. The residue dissolves in dichloromethane, 8. For example, washing with aqueous sodium sulfate solution and brine, 9. Dry and concentrate under reduced pressure to obtain the crude product, 10. A method comprising recrystallizing the crude product from tert-butyl methyl ether.

[0408] Embodiment K7 A method for preparing crystalline polymorph II according to either Embodiment K1 or K2, comprising heptane trituration.

[0409] Embodiment K7a A method for preparing the crystalline polymorph II described in either Embodiment K1 or K2, 1. Dissolving N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide in diethyl ether, 2. For example, adding CuBr.SMe2, 3. For example, adding 2,2'-bis(diphenylphosphine)-1,1'-binaphthalene, 4. Stir the reaction mixture for a period of 20 minutes as shown, 5. Cooling the reaction mixture, 6. For example, adding trimethylsilyltrifluoromethanesulfonate, 7. Stir for the period exemplified by 20 minutes, 8. Adding 3-(trifluoromethyl)phenyl)magnesium bromide, Stir for the period exemplified by 9.2 hours, 10. Quenching the reaction mixture in, for example, an aqueous solution of NH4Cl, 11. Extraction with ethyl acetate, 12. Wash the combined organic layers with brine solution, 13. Dry with Na2SO4 and concentrate to obtain the crude product. 14. For example, purification by column chromatography using ethyl acetate / hexane (20:80) as the eluent, 15. A method comprising triturating the obtained solid with heptane (5 mL).

[0410] Embodiment M1 The following formula: [ka] (In the formula, each R ζ A saturated target of Formula 1 as defined in Embodiment B1, combined with an amount of one of the following: a marker, an impurity, or a degradable compound (as defined in any one of Embodiments A1 to A52 and B1).

[0411] Embodiment M2 The following formula: [ka] A saturated target of Formula 1 as defined in Embodiment B1, combined with one of the following amounts: a marker, an impurity, or a degradable compound.

[0412] Embodiment M3 The following formula: [ka] A saturated target of Formula 1 as defined in Embodiment B1, combined with one of the following amounts: a marker, an impurity, or a degradable compound.

[0413] Embodiment M4 The following formula: [ka] (In the formula, each R θ and each R ζ A saturated target of Formula 1 as defined in Embodiment B1, combined with an amount of any one of a marker, an impurity, or a degradable compound (as defined in Embodiment A2).

[0414] Embodiment N1 General procedure for preparing conserved markers from saturated targets: [ka] (In the ceremony R β , A β , A α and R ζ (This has the same meaning as defined in Embodiment A2).

[0415] Embodiment N2 A general procedure for preparing storage markers useful for pH-dependent calibration, based on three aqueous compositions of buffered saturated targets, each at a different pH. Three lots of approximately 50 mg of saturated target are each suspended in approximately 2 ml of 2% acetonitrile aqueous solution and sonicated for approximately 20 minutes. Add approximately 0.1 ml of one of three different buffer solutions to pH=4, pH=7, and pH=10, respectively. Each of the three buffer solutions was filtered and introduced into a quartz tube, then exposed to natural sunlight for approximately two months. do. Analysis by HPLC-MS reveals the formation of corresponding storage markers in solutions of pH-related concentrations.

[0416] Embodiment P1 Compounds of the following formula [ka] or its salt or N-oxide (In the formula, Each R ζ (This has the same meaning as defined in Embodiment A2).

[0417] Embodiment P1a A synthetic intermediate compound for preparing a saturated target of the following formula, [ka] or its salt or N-oxide (in the formula, R ζ (This has the same meaning as defined in Embodiment A2).

[0418] Embodiment P2 Compounds of the following formula [ka] or its salt or N-oxide.

[0419] Embodiment P2a A synthetic intermediate compound for preparing a saturated target of the following formula, [ka] or its salt or N-oxide.

[0420] Embodiment P3 Compounds of the following formula [ka] or its salt or N-oxide.

[0421] Embodiment P3a A synthetic intermediate compound for preparing a saturated target of the following formula, [ka] or its salt or N-oxide.

[0422] Embodiment Q1 Compounds of the following formula [ka] or its salt or N-oxide (In the formula, Each R ζ (This has the same meaning as defined in Embodiment A2).

[0423] Embodiment Q2 Compounds of the following formula [ka] or its salt or N-oxide.

[0424] Embodiment Q3 Compounds of the following formula [ka] or its salt or N-oxide. [Examples]

[0425] Preparation A Preparation of N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide from N-methylpyrrolidone (1-methylpyrrolidine-2-one) as an exemplary example of the synthetic intermediate compound of Embodiment E1. For example, 1-methylpyrrolidine-2-one in THF is cooled to -75°C to -78°C and maintained within that range. For example, lithium diisopropylamide is added to THF.

[0426] Stir the reaction mixture for, for example, about 30 minutes. Add, for example, 1-fluoro-2-isocyanatobenzene dissolved in THF dropwise over, for example, about 5 minutes.

[0427] Warm the reaction mixture to ambient temperature and stir it for, for example, about 2 hours.

[0428] The reaction mixture is quenched with, for example, saturated NH4Cl and extracted with, for example, ethyl acetate.

[0429] The combined organic layers are washed with saturated NaCl solution, dried over, for example, Na2SO4, and concentrated to obtain the crude compound.

[0430] The crude compound is purified by column chromatography, for example, using ethyl acetate / hexane as the eluent, to obtain N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide. [ka]

[0431] Specific example: 10.08 mmol of 1-methylpyrrolidine-2-one (1 gm) in 10 ml of THF (10 vol) was cooled to 75°C to 78°C. 20.16 mmol of 2 M lithium diisopropylamide (2.16 gm) was added to 10.1 ml of THF at the same temperature of approximately -75°C to -78°C.

[0432] The reaction mixture was stirred at approximately -75°C to -78°C for about 30 minutes.

[0433] 10.08 mmol of 1-fluoro-2-isocyanatobenzene (1.4 gm) dissolved in THF (5 ml) was added dropwise over approximately 5 minutes.

[0434] The reaction mixture was heated to approximately 20°C to -25°C and stirred for about 2 hours.

[0435] The reaction mixture was quenched with saturated NH4Cl and extracted with ethyl acetate.

[0436] The combined organic layers were washed with saturated NaCl solution, dried over Na2SO4, and concentrated to obtain the crude compound.

[0437] The crude compound was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent to obtain 400 mg of N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide as a light brown solid, which approximated a yield of approximately 17%. Analysis by HPLC revealed a purity of approximately 88%. 1 H-NMR(DMSO-d6):δ 10.08(s,1H)8.04-7.98(m,1H),7.29-7.24(m,1H),7.17-7.12(m,2H),3.7 3-3.68(t,8.8Hz,1H),3.39-3.36(m,2H),2.77(s,3H),2.25-2.20(m,2H). LCMS(EI): m / z 237.3 [M+1].

[0438] Preparation B Preparation of the synthetic intermediate N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide, as an example of the compound of formula 3 defined earlier, from N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide. N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide is dissolved in, for example, THF. Then, for example, sodium hydride is added at a temperature of, for example, about 0°C to -5°C.

[0439] The reaction mixture is stirred, for example, at a temperature of about 0°C to -5°C for about 20 minutes. Then, diphenyl disulfide dissolved in THF is added, for example, at a temperature of about 0 to 5°C.

[0440] The reaction mixture is stirred, for example, at approximately 20°C to 25°C for approximately 12 hours.

[0441] The reaction mixture is quenched in, for example, an aqueous solution of NH4Cl, and extracted with two lots of, for example, ethyl acetate (twice).

[0442] The combined organic layers are washed with, for example, a saturated NaCl solution, dried with, for example, Na2SO4, and concentrated to obtain the crude compound.

[0443] The crude compound is purified, for example, by column chromatography using silica gel with ethyl acetate / hexane as the eluent, to obtain N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylthio)pyrrolidine-3-carboxamide as a solid. [ka]

[0444] Specific example: 21.18 mmol of N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide (5 gm) was dissolved in 50 ml of THF (10 vol). 42 0.37 mmol of sodium hydride (1 g) was added at a temperature of approximately 0°C to -5°C.

[0445] The reaction mixture was stirred at a temperature of approximately 0°C to -5°C for about 20 minutes. 25.42 mmol of diphenyl disulfide (5.5 g) dissolved in THF (5 ml) was added at a temperature of approximately 0 to 5°C.

[0446] The reaction mixture was stirred at approximately 20°C to 25°C for about 12 hours.

[0447] The reaction mixture was quenched in an NH4Cl aqueous solution and extracted with approximately 50 ml of ethyl acetate (twice) from two lots.

[0448] The combined organic layers were washed with saturated NaCl solution, dried over Na2SO4, and concentrated to obtain the crude compound.

[0449] The crude compound was purified by silica gel column chromatography using ethyl acetate / hexane as the eluent to obtain 3.8 gm of N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylthio)pyrrolidine-3-carboxamide as a grayish-white solid, which approximated a yield of approximately 52% and had a purity of approximately 98% by LC-MS analysis. 1 H-NMR(DMSO-d6):δ 10.16(s,1H)8.15-8.13(t,8Hz,1H),7.50-7.43(m,3H),7.38-7.34(m,2H),7.24-7.29(m,1H),7.19-7.1 1(m,2H),3.30-3.27(dd,8Hz,1H),3.22-3.25(m,1H),2.81(s,3H)2.70-2.62(m,1H),2.22-2.16(m,1H). LCMS(ES): m / z 345.4 [M+1].

[0450] Preparation C Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide as an example of an unsaturated precursor from N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylthio)pyrrolidine-3-carboxamide. N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylthio)pyrrolidine-3-carboxamide is dissolved in, for example, acetic acid and stirred for, for example, about 20 minutes. Then, for example, meta-chloroperoxybenzoic acid is added little by little at, for example, ambient temperature. The reaction mixture is stirred for, for example, about 2 hours.

[0451] The reaction mixture is quenched, for example, in an aqueous solution of NaHCO3, and extracted twice with, for example, ethyl acetate. The combined organic layers are concentrated to obtain the crude compound. [ka]

[0452] Specific example: 0.29 mol of N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylthio)pyrrolidine-3-carboxamide (100 mg) was dissolved in 2 ml of acetic acid (20 vols) and stirred for about 20 minutes to obtain a substantially clear solution. 0.29 mmol of meta-chloroperbenzoic acid (50 mg mCPBA) was added in portions at approximately 20°C to 25°C. The reaction mixture was stirred at approximately 20°C to 25°C for about 2 hours. Then the reaction mixture was converted to NaHCO3 The solution was quenched and extracted twice with ethyl acetate. The combined organic layers were concentrated to obtain the crude compound. Analysis of the crude material by LC-MS revealed N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide in approximately 48% yield. 1 H-NMR(DMSO-d6):δ 11.16(s,1H),8.41-8.36(dt,8Hz,1H),8.09(s,1H)7.35-7.30(m,1H),7.23-7.12(m,2H),4.26(s,2H),3.03(s,3H).LCMS(EI):m / z 393.4 [M+1].

[0453] Preparation D1 Synthesis of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as an exemplary saturated target from the corresponding unsaturated precursor, N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide, using trimethylsilyl chloride and BINAP. N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide is dissolved in, for example, diethyl ether, then copper(I) dimethyl sulfide complex is added, followed by the addition of R-BINAP. [ka]

[0454] The reaction mixture is stirred for, for example, about 20 minutes. The reaction mixture is maintained at a low temperature, such as approximately -20°C to -25°C. Trimethylsilyl chloride is added and stirred for, for example, about 10 minutes. Then, for example, a solution of 3-(trifluoromethyl)phenyl)magnesium bromide is added and stirred for, for example, about 2 hours. The reaction mixture is quenched with, for example, an aqueous solution of NH4Cl and extracted with, for example, ethyl acetate. The combined organic layers are washed with, for example, a saturated brine solution, dried with, for example, Na2SO4, and concentrated to obtain the crude product. [ka]

[0455] Specific example: 2.13 mmol of N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (500 mg) was dissolved in 25 ml of diethyl ether. 0.1 mmol of copper(I) bromide dimethyl sulfide complex (22 mg CuBr.SMe2) was added, followed by 0.12 mmol of R-BINAP (approximately 75 mg) at a temperature of approximately -20°C to 25°C.

[0456] The reaction mixture was stirred at approximately -20°C to -25°C for about 20 minutes.

[0457] The reaction mixture was maintained at approximately -20°C to -25°C. Approximately 4.7 mmol of trimethylsilyl chloride (approximately 506 mg) was added and stirred for approximately 10 minutes. 6.39 mmol of 1.6 A 2M, 3-(trifluoromethyl)phenyl)magnesium bromide solution (1.6 gm, 3.9 ml) was added at a temperature of approximately -20 to -25°C and stirred for about 2 hours.

[0458] The reaction mixture was quenched in an aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic layer was washed with saturated brine, dried over Na2SO4, concentrated, and measured by quantitative HPLC analysis, which yielded a crude assay-corrected yield of approximately 77%, to obtain approximately 1 g of crude product with a purity of approximately 54%. 1 H-NMR(DMSO-d6):δ 10.11(s,1H),7.99-7.95(m,1H)7.74(s,1H),7.69-7.68(m,1H),7.63-7.58(m,2H),7.28-7.24(m, 1H),7.15-7.12(m,2H),4.08-4.02(m,2H),3.82-3.77(t,8Hz,1H),3.48-3.47(m,1H),2.84(s,3H). LCMS(ES): m / z 381.5 [M+1].

[0459] Preparation D2 Synthesis of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as an exemplary saturated target from N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide as the corresponding unsaturated precursor, using trimethylsilyl trifluoromethanesulfonate and (S)-N-((S)-1-(butylamino)-1-oxo-3-phenylpropan-2-yl)-2-(((E)-2-(diphenylphosphanail)benzylidene)amino)-3-methylbutanamide as the corresponding unsaturated precursor. [ka]

[0460] 2.13 mmol of N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (500 mg) was dissolved in 25 ml of diethyl ether. 0.1 mmol of copper(I) bromide dimethyl sulfide complex (22 mg CuBr.SMe2) was added, followed by 0.12 mmol of (S)-N-((S)-1-(butylamino)-1-oxo-3-phenylpropan-2-yl)-2-(((E)-2-(diphenylphosphanyl)benzylidene)amino)-3-methylbutanamide (76 mg) at 20-25°C. [ka]

[0461] The reaction mixture was stirred at approximately 20°C to 25°C for about 20 minutes. The reaction mixture was cooled and maintained at -20°C to -25°C, and trimethylsilyl trifluoromethanesulfonate (1 g) was added. [ka] Add the ingredients and stir for about 10 minutes.

[0462] 6.39 mmol of 1.62 M 3-(trifluoromethyl)phenyl)magnesium bromide (1.6 gm, 3.9 ml) [ka] The mixture was added at a temperature of approximately -20 to -25°C and stirred for about 2 hours. The reaction mixture was quenched in an aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic layer was washed with saturated brine, dried over Na2SO4, and concentrated to obtain the product, which was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent to obtain 210 mg of (anti)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as a grayish-white solid with a yield of approximately 26%. Analysis by HPLC revealed a purity of approximately 67%. The product contained enantiomers of R, R / S, S, etc., in a 1:1.32 ratio as determined by chiral HPLC analysis.

[0463] Preparation D3 Synthesis of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide as an exemplary saturated target, avoiding the use of trimethylsilyl Lewis acids, such as TMSI, TMSCl, TMSOTf, etc., from N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as an exemplary saturated target, from N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide as a corresponding unsaturated precursor. 2.13 mmol of N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (500 mg) was dissolved in 25 ml of diethyl ether. 0.12 mmol of R-BINAP (approximately 75 mg) was added at a temperature of approximately 20°C to 25°C, and the reaction mixture was stirred for approximately 20 minutes. 6.39 mmol of 1.62 M, 3-(trifluoromethyl)phenyl)magnesium bromide (1.6 gm, 3.9 ml) was added at a temperature of approximately -20 to -25°C, and the mixture was stirred for approximately 2 hours.

[0464] The reaction mixture was quenched in an aqueous NH4Cl solution and extracted twice with ethyl acetate (2 × 25 mL). The combined organic layers were washed with saturated brine, dried over Na2SO4, and concentrated to obtain 260 mg of crude product, which was (anti)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as a grayish-white solid. The yield was 32%, and the purity was approximately 94% as measured by HPLC.

[0465] Preparation D4 Boron trifluoride-diethyl ether complex, BF3.Et2O, from N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide as the corresponding unsaturated precursor, is used as an example saturated target (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(tri Synthesis of fluoromethyl)phenyl)pyrrolidine-3-carboxamide. 0.42 mmol of N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (100 mg) was dissolved in 5 ml of diethyl ether.

[0466] 0.02 mmol of copper(I) bromide dimethyl sulfide complex (4 mg CuBr.SMe2) was added, followed by the addition of 0.02 mmol of BINAP (15 mg) at 20-25°C.

[0467] The reaction mixture was stirred at approximately 20°C to 25°C for about 20 minutes.

[0468] The reaction mixture was cooled and maintained at approximately -20°C to -25°C, and 0.92 mmol of diethyl boron trifluoride (0.12 mL) was added and stirred for approximately 20 minutes.

[0469] Approximately 1.26 mmol of magnesium 3-(trifluoromethyl)phenyl)bromide (0.78 mL of 1.62 M) was added at approximately -20°C to -25°C, and the mixture was stirred for about 2 hours.

[0470] The reaction mixture was quenched in an aqueous NH4Cl solution and extracted twice with ethyl acetate (2 × 5 mL). The combined organic layer was washed with saturated brine, dried over Na2SO4, and concentrated to obtain 300 mg of crude (anti)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide. The yield exceeded 6%, and the purity was approximately 12% as measured by HPLC.

[0471] Preparation E Preparation of storage markers from three exemplary compositions of tetoflupyrrolimeth as saturated targets, each buffered at a different pH. [ka] Three lots containing approximately 50 mg of tetoflupyrrolimeth were each suspended in approximately 2 ml of 2% acetonitrile aqueous solution and subjected to sonication for approximately 20 minutes.

[0472] Approximately 0.1 ml of each different buffer solution (pH=4, pH=7, and pH=10) was added to each sample.

[0473] Each of the three solutions is filtered and introduced into a quartz tube, then exposed to natural sunlight for approximately two months.

[0474] Analysis by HPLC-MS showed the formation of storage markers in each solution.

[0475] Solutions buffered at pH 4 and pH 10 contained approximately an order of magnitude higher concentrations of the preservation marker compared to the solution buffered at pH 7.

[0476] LC / MS method for saturated target

[0380] and storage marker-impurity

[0286] Column: Agilent Zorbax Eclipse XDB C18, 150×4.6mm ID, 5.0μm Injection volume: 5μL Oven temperature: 40℃ Detector: UV, λ=230, 250, 280nm • Conditions for a solvent delivery system at a flow rate of 0 ml / min:

[0477] [Table 1]

[0478] Preparation F Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide from (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide. [ka] Flame-dry a 5 mL round-bottom flask and purge it with argon.

[0479] Add 0.009 mmol (2 mg) of Striker reagent [(PPh3)CuH]6 as a pre-catalyst / catalyst, and either (R)-DTBM-SEGPHOS or (S)-(+)-DTBM-SEGPHOS as a pre-catalyst / catalyst. [ka]

[0480] Add 1 ml of THF and cool the solution to approximately 0°C. Add 3.36 mmol (224 μl) of polymethylhydrosiloxane (PMHS) as a hydride source, introducing it, for example, via a syringe, followed by the introduction of 1.81 mmol (173 μl) of t-BuOH and 0.83 mmol (313 mg) of N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide. Stir the mixture at approximately 0°C until the reaction is complete, typically as demonstrated by quantitative TLC for 3 to 12 hours.

[0481] The reaction mixture is quenched by pouring it into saturated NaHCO3, diluted with an aqueous solution of diethyl ether (Et2O / H2O), and then stirred at ambient temperature for approximately 2 hours.

[0482] The aqueous layer is extracted twice with diethyl ether, the combined organic layers are washed with brine, dried over anhydrous MgSO4, filtered, and concentrated by rotary evaporation.

[0483] The obtained crude material is purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent to obtain (anti)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as a grayish-white solid. HPLC analysis shows a purity of approximately 90% and a yield of about 70%. A chiral HPLC analysis theoretically yields an enantiomer ratio of approximately 1:9. Depending on the selection of chiral catalyst components, the enantiomer excess can be directed towards the desired product. This preparation and other specific preparations can also be carried out using alternative reagents and conditions that will be understood by those skilled in the art to have equivalent functionality and / or effects.

[0484] Preparation G Synthesis of 1-methyl-2-oxopyrrolidine-3-carboxylic acid: [ka] 50.5 mmol of 1-methylpyrrolidine-2-one (5 g) was dissolved in 50 ml of THF (10 volumes), cooled to approximately -75°C to -78°C, and maintained at that temperature.

[0485] 101 mmol of 2M lithium diisopropylamide (10.2 gm, 50 ml) was added at approximately -75°C to -78°C. The reaction mixture was stirred at -75°C to -78°C for approximately 30 minutes. The reaction mixture was added dropwise onto solid CO2 and stirred for approximately 1 hour. The reaction mixture was gradually heated to approximately 20°C to 25°C and stirred for approximately 1 hour. The reaction mixture was quenched with dilute HCl, extracted with 10% isopropyl alcohol in dichloromethane (4 × 25 ml), dried over Na2SO4, and concentrated to obtain 2.2 gm of crude product.

[0486] 1-Methyl-2-oxopyrrolidine-3-carboxylic acid was obtained as a brown oily substance. Yield by HPLC was 30.5%, purity approximately 58%.

[0487] Preparation H Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide using propylphosphonic anhydride (T3P) [ka] 6.99 mmol of 1-methyl-2-oxopyrrolidine-3-carboxylic acid (1 g) was dissolved in 20 ml of dimethylformamide (20 vol) and cooled to approximately 0-5°C. 20.97 mmol of triethylamine (2.1 g) and 7.68 mmol of 2-fluoroaniline (850 mg) were added, followed by the addition of 13.98 mmol of T3P (9 ml of 50% solution in ethyl acetate) at 0°C-5°C. The reaction mixture was stirred at approximately 0°C--5°C for about 2 hours. The reaction mixture was added to water and extracted with 2 × 150 ml of ethyl acetate. The combined organic layer was washed with water, followed by brine solution, dried over sodium sulfate, and concentrated to obtain the crude product. The crude product was dissolved in 5 ml of dichloromethane and precipitated with 20 ml of n-heptane. The solid was stirred and filtered to obtain 700 mg of N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide as a grayish-white solid. HPLC analysis revealed a purity of approximately 99% and a yield of 42.4%.

[0488] Preparation I Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide via acyl chloride [ka] 13.98 mmol of 1-methyl-2-oxopyrrolidine-3-carboxylic acid (2 g) was dissolved in 20 ml of dichloromethane (10 vol). 2.73 mmol of dimethylformamide (0.2 ml) was added, and the mixture was cooled to approximately 0°C to 5°C. 20.97 mol of oxalyl chloride (2.6 g) was added at approximately 0°C to 5°C. The reaction mixture was stirred at approximately 0 to 5°C for about 2 hours. Acyl chloride formation was monitored by TLC by quenching in ethyl alcohol.

[0489] The reaction mixture was concentrated to dryness, diluted with fresh dichloromethane, and added at approximately 0°C to 5°C to a stirred solution of 13.98 mmol of 2-fluoroaniline (1.5 g) and 27.96 mmol of triethylamine (2.8 g) in 10 ml of dichloromethane (5 vol).

[0490] The reaction mixture was heated to approximately 20°C to 25°C and stirred for about 2 hours. The reaction mixture was quenched in water and extracted with dichloromethane (2 × 150 ml). The combined organic layers were washed with water, followed by brine solution, dried over sodium sulfate, and concentrated to obtain the crude product. 500 mg of N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide was obtained. Yield was 15.1% and purity was 88.8% by LC-MS.

[0491] Preparation J Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylselenyl)pyrrolidine-3-carboxamide [ka] 63.5 mmol (15 g) of N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide was dissolved in 60 ml of THF. 127.1 mmol of NaH (3.0 g) was added at approximately 0°C to 5°C. The reaction mixture was stirred at approximately 0°C to 5°C for about 20 minutes. 69.9 mmol of phenylselenyl bromide (16.5 g) dissolved in THF was added at approximately 0°C to 5°C, and the mixture was stirred at 0°C to 5°C for about 2 hours. The reaction mixture was quenched in ice-cold water and extracted with ethyl acetate. The combined organic layers were concentrated to obtain the crude compound, which was purified by silica gel column chromatography using ethyl acetate / hexane as the eluent to obtain 24 g of N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylselenyl)pyrrolidine-3-carboxamide as a grayish-white solid. Yield by LC-MS = 96%, purity = 97.1%. 1 H-NMR(DMSO-d6):δ 10.26(s,1H),8.20-8.16 (m,1H),7.59-7.56(m,2H),7.47-7.43(m,1H),7.35-7.31(m,2H),7.27-7.22(m,1H),7.19-7.15(m,1H),7. 13-7.11(m,1H),3.30-3.25(m,1H),3.18-3.12(m,1H),2.77(s,3H),2.55-2.64(m,1H),2.18-2.13(m,1sH). LCMS(EI): m / z 393.4 (M+1).

[0492] Preparation K A process scheme starting from the compound of Embodiment E1 via the compound of Embodiment C1a, then starting from the compound of Embodiment E1 via an unsaturated precursor compound of Embodiment A1 or Embodiment A2, and using a saturated target exemplified by tetoflupyrrolimeth, but not limited thereto. Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide [ka] 38.2 mmol of N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylceranyl)pyrrolidine-3-carboxamide (15 g) was dissolved in 150 ml of dichloromethane (MDC 10 vol). 76.5 mmol of H2O2 (2.6 ml) was added at approximately 0-5°C. The reaction mixture was stirred at 0-5°C for approximately 2 hours. The reaction mixture was quenched in ice-cold saturated NaHCO3 solution. The resulting solid was stirred, filtered, and vacuum-dried. The resulting solid was suspended in 150 ml of n-heptane, stirred, filtered, and dried to obtain 7.1 g / m of N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (unsaturated precursor) as a grayish-white solid. Yield by LC-MS = 79.3%, purity = 98.1%. 1 H-NMR(DMSO-d6):δ 11.16(s,1H),8.41-8.36(dt,8Hz,1H),8.09(s,1H)7.35-7.30(m,1H),7.23-7.12(m,2H),4.26(s,2H),3.03(s,3H).LCMS(EI):m / z 393.4 [M+1].

[0493] Preparation L Tetoflupyrrolimite Polymorph I Preparation of polymorphisms: [ka] (3R,4S)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylic acid (21.2 g, 73.8 mmol) (International Publication No. 2018 / 175226) was dissolved in acetonitrile (200 mL), and 2-fluoroaniline (9.02 g, 81.2 mmol) and N-methylimidazole (30.3 g, 369 mmol) were added to the solution. The resulting mixture was stirred at ambient temperature for 10 minutes, and chloro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate (22.8 g, 81.2 mmol) was added to the mixture all at once. The resulting mixture was stirred at ambient temperature for 10 hours, and then the solvent was evaporated, and the residue was drained in dichloromethane (500 mL). The mixture was dissolved in ( ), washed with saturated aqueous sodium sulfate solution (2 × 100 mL) and brine (1 × 100 mL), dried, and concentrated under reduced pressure to obtain the crude product. This was recrystallized from tert-butyl methyl ether (20 mL), and by chiral HPLC, (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide (10.1 g, 36%) having a chiral enantiomer ratio of more than 99:1 was obtained.

[0494] Preparation M (Tetoflurylrometh polymorph II) [ka] In a 50 mL two-necked round-bottom flask, N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (500 mg, 2.13 mmol) was dissolved in dry diethyl ether (25 mL), CuBr.SMe2 (22 mg, 0.1 mmol) was added, followed by 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (79 mg, 0.12 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 20 minutes. The reaction mixture was cooled to -20 to -25 °C using dry ice / acetonitrile, and trimethylsilyl trifluoromethanesulfonate (1 gm, 4.68 mmol) was added and stirred for 20 minutes. 1.62 M 3-(trifluoromethyl)phenyl)magnesium bromide was added via a 5 mL syringe (1.6 g m, 6.39 mmol, 3.9 ml) at -20 to -25°C and stirred for 2 hours. At this point, TLC analysis indicated completion of the reaction (30:70 ethyl acetate:hexane, starting material 0.3 R). f , R f Product 0.5). The reaction mixture was quenched in NH4Cl aqueous solution (20 mL) and extracted with ethyl acetate (3 × 50 mL). The combined organic layers were washed with saturated brine solution (100 mL), dried over Na₂SO₄, and concentrated in a 250 mL round-bottom flask under a vacuum of 600 mmHg at 40°C for 30 minutes at 60 rpm to obtain a crude product (1 g). This was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane (20:80) as the eluent. The resulting solid was tritulated with heptane (5 mL), and 360 mg of anti-(3,4)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide with a chiral enantiomer ratio of 50.5:49.4 was obtained as a grayish-white solid (HPLC yield 44.3%, purity 94.6%) by chiral HPLC.

[0495] Preparation N Synthesis of 4-ethyl-N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide using organozinc. [ka] (S)-N-((S)-1-(butylamino)-1-oxo-3-phenylpropane-2-yl)-2-(((E)-2-(diphenylphosphanyl)benzylidene)-amino)-3-methylbutanamide (75 mg, 0.12 mmol) and copper(I) trifluoromethanesulfonate benzene complex (CuOTf)2·C6H6 (25 mg, 0.05 mmol) are dissolved in toluene (6 ml, 20 volumes) to form N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (30 (0 mg, 1.28 mmol) was added and stirred at 20-25°C for 10 minutes. The reaction mixture was cooled to -35-30°C and diethylzinc (3.84 mL, 1 M, 3 equivalents) was added to the reaction mixture. The reaction mixture was left to stir at -35-30°C for 4 hours. The reaction mixture was quenched in an aqueous NH4Cl solution and extracted with ethyl acetate (2 × 25 mL). The combined organic layers were washed with saturated brine, dried over Na2SO4, and concentrated to obtain the crude product. This crude product was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent, and 120 mg of 4-ethyl-N-(2-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide with a chiral enantiomer ratio of 49.4:49.4 was obtained as a grayish-white solid (yield 35.5%, purity 88.9% by HPLC and 58.3% by LCMS). LCMS(ES): m / z 265.2 (M+1).

[0496] Preparation O Synthesis of N-(2,3-difluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide using propylphosphonic anhydride (T3P). [ka] 1-Methyl-2-oxopyrrolidine-3-carboxylic acid (5 g, 34.9 mmol) was dissolved in dimethylformamide (20 ml, 4 volumes), cooled to 0°~5°C, and triethylamine (10.5 g, 103.9 mmol), 2,3-difluoroaniline (4.9 g, 37.9 mmol), followed by T3P-propylphosphonic anhydride (44 g, 138.3 mmol; 50% solution in ethylammonium) were added at 0°~5°C. The reaction mixture was stirred at 0~5°C for 2 hours. The reaction mixture was added to water and extracted with ethyl acetate (2 × 50 ml). The combined organic layer was washed with water, followed by brine solution, dried over sodium sulfate, and concentrated to obtain a solid.

[0497] To this, solid heptane (10 volumes) was added, the mixture was stirred for 1 hour, filtered, and dried under vacuum to obtain 8 g of N-(2,3-difluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide as a grayish-white solid. Yield was 90.9% and purity was 98.9% by LC-MS. 1 H NMR(DMSO-d6):δ 10.27(s,1H),7.95-7.77(m,1H),7.21-7.16(m,2H),3.74-3.69(t,18Hz,1H),3.43-3.32(m,2H),2.89(s,3H),2.32-2.20(m,2H).LCMS(EI):m / z 255.2(M+1).

[0498] Preparation P Synthesis of N-(2,3-difluorophenyl)-1-methyl-2-oxo-3-(phenylceranyl)pyrrolidine-3-carboxamide: [ka] N-(2,3-difluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide (2g, 7.8 mmol) was dissolved in THF (20 ml), and NaH (0.629 g, 26.2 mmol) was added at 0-5°C. The reaction mixture was stirred for 20 minutes at 0-5°C. Phenylselenyl bromide (2g, 8.5 mmol) dissolved in THF (5 mL) at 0-5°C was added, and the mixture was stirred for 2 hours. The reaction mixture was quenched in cold water and ethyl acetate (2 × 5 Extraction was performed using 0 mL of solvent. The combined organic layers were concentrated to obtain the crude compound, which was purified by silica gel column chromatography using ethyl acetate / hexane as the eluent to obtain 2.2 g of N-(2,3-difluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide as a pale yellow solid. Yield was 68.7% and purity 98.2% by LC-MS. 1H NMR(DMSO-d6):δ 10.4(s,1H),7.99-7.94(m,1H),7.58-7.56(m,2H),7.47-7.43(m,1H),7.35-7.31(m,2H),7.20-7.12(m ,2H),3.31-3.27(m,1H),3.18(m,1H),2.79(s,3H),2.64-2.55(m,1H),2.18-2.13(m,1H).LCMS(EI):m / z 411.2(M+1).

[0499] Preparation Q Synthesis of N-(2,3-difluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide [ka] N-(2,3-difluorophenyl)-1-methyl-2-oxo-3-(phenylselenyl)pyrrolidine-3-carboxamide (2 g, 4.8 mmol) was dissolved in dichloromethane (20 ml, 10 volumes), and H2O2 (1.1 g, 32.3 mmol; 30% solution) was added at 0-5°C. The reaction mixture was stirred at 0-5°C for 2 hours. The reaction mixture was quenched in ice-cold saturated NaHCO3 solution and extracted with dichloromethane (2 × 50 mL). The organic layer was washed with NaHCO3 solution (3 × 20 mL), dried under Na2SO4, and concentrated to obtain the crude product. The crude compound was suspended in IPA (5 mL), stirred for 2 hours, filtered, and dried to obtain 1 g of N-(2,3-difluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide as a pale yellow solid (yield 83.3% and purity 96.1% by LC-MS). 1H NMR(CDCl3):δ 11.1(s,1H),8.24-8.20(m,1H),8.0-7.99(bt,1.6Hz,1H)7.10-7.03(m,1H),6.99-6.90(m,1H),4.12-4.11(bd,2H),3.16(s,3H).LCMS(EI):m / z 253.2(M+1).

[0500] Preparation R Synthesis of N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-(6-(trifluoromethyl)pyridine-3-yl)pyrrolidine-3-carboxamide. [ka] In a 25 mL two-necked round-bottom flask, 5-bromo-2-(trifluoromethyl)pyridine (0.80 g, 3.57 mmol) was dissolved in dry diethyl ether (8 mL, 10 volumes). The reaction mixture was cooled to -78 to -70°C, and n-butyllithium (4.26 mL, 2.5 M, 3 equivalents) was added to the reaction mixture. The reaction mixture was stirred at -78 to 70°C for 1 hour. In a separate flask, N-(2,3-difluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (0.3 g, 1.19 mmol) and copper(I) bromide dimethyl sulfide complex (12.2 mg) were added in Et2O (9 mL, 30 volumes). 0.059 mmol) and 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (44.4 mg, 0.071 mmol) were added, and the reaction mixture was cooled to -78~70°C. Lithium-conjugated 5-bromo-2-(trifluoromethyl)pyridine was added dropwise to this reaction mixture at -78~70°C and stirred for 1 hour. The reaction mixture was quenched in an aqueous NH4Cl solution and extracted with ethyl acetate (2 × 50 mL). The combined organic layers were washed with saturated brine solution, dried over Na2SO4, and concentrated to obtain the crude product, which was purified by column chromatography using silica gel (60~120 mesh) with ethyl acetate / hexane as the eluent to obtain 60 mg of N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-(6-(trifluoromethyl)pyridine-3-yl)pyrrolidine-3-carboxamide as a pale yellow solid. Yield of 12.7% and purity of 67.1% by LC-MS. 1H NMR(CDCl3):δ 10.06(s,1H),7.96-7.89(m,2H),7.03-6.99(m,2H),6.93- 6.89(m,2H),4.21-4.18(m,1H),3.87-3.82(m,1H),3.65-3.63(m,1H),3.54-3.49(m,1H),3.05(s,3H).LCMS(ES):m / z 400.3(M+1).

[0501] Preparation S Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-4-(6-(trifluoromethyl)pyrrolidine-3-yl)pyrrolidine-3-carboxamide [ka] In a 25 mL two-necked round-bottom flask, 5-bromo-2-(trifluoromethyl)pyridine (0.84 g, 3.73 mmol) was dissolved in dry diethyl ether (8 mL, 10 volumes). The reaction mixture was cooled to -78 to -70°C, and n-butyllithium (4.4 mL, 2.5 M, 3 equivalents) was added to the reaction mixture. The reaction mixture was stirred at -78 to 70°C for 1 hour. In a separate flask, N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (0.3 g, 1.28 mmol), copper(I) bromide dimethyl sulfide complex (13 mg, 0.063 mmol), and 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (47 mg, 0.075 mmol) were taken from Et2O (9 mL, 3 volumes), and the reaction mixture was cooled to -78 to 70°C. Lithium-5-bromo-2-(trifluoromethyl)pyridine was added dropwise to this reaction mixture (RM) at -78 to 70°C, and the mixture was stirred for 1 hour. The reaction mixture was quenched in aqueous NH4Cl solution and extracted with ethyl acetate (2 × 50 mL). The combined organic layers were washed with saturated brine solution, dried over Na2SO4, and concentrated to obtain the crude product. This crude product was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent to obtain 50 mg of N-(2-fluorophenyl)-1-methyl-2-oxo-4-(6-(trifluoromethyl)pyrrolidine-3-yl)pyrrolidine-3-carboxamide as an oily liquid (10.2% yield and 49.1% purity by LC-MS). LCMS(ES): m / z 382.3 (M+1).

[0502] Preparation T Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide from N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide (Procedure 1) [ka] In a 25 mL round-bottom flask (RBF), N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide (100 mg, 0.26 mmol) was dissolved in acetic acid (5 ml, 50 vol). The reaction mixture was cooled to 0-5°C, and Zn powder (0.17 g, 2.64 mmol) was added. The reaction mixture (RM) was stirred at 20-25°C for 12 hours. The RM was filtered and concentrated to obtain the crude product. Crude LCMS showed 30.6% anti-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide. LCMS(ES): m / z 381.3 (M+1).

[0503] Preparation U Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide from N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide (Preparation Procedure No. 2) [ka] N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide (50 mg, 0.13 mmol) was dissolved in methanol (5 ml, 50 vol) in 25 mL of RBF. The reaction mixture was cooled to 0-5°C, and nickel(II) chloride hexahydrate (15 mg, 0.06 mmol) was added, followed by sodium borohydride (5 mg, 0.13 mmol). The RM was stirred at 20-25°C for 12 hours. The reaction was monitored by LC-MS. LC-MS showed the formation of the desired mass up to approximately 15%. LCMS(ES): m / z 381.3 (M+1).

[0504] Preparation V Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide from N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide [ka] N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide (50 mg, 0.13 mmol) was dissolved in methanol (5 ml, 50 vol) in 25 mL of RBF, and tris(triphenylphosphine)rhodium(I) chloride (12 mg, 0.013 mmol) was added. RM was stirred under H2 pressure. Pressure was applied using a hydrogen bladder at 20-25°C for 12 hours. The reaction was monitored using LC-MS. RM was converted to 2N Na The solution was quenched with OH solution (0.2 mL), extracted with ethyl acetate (2 × 5 mL), and concentrated to obtain the crude product. Crude LC-MS showed formation of the desired mass up to approximately 10%. LCMS(ES): m / z 381.2 (M+1).

[0505] Preparation W Synthesis of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide from N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide (Procedure - No. 3). [ka] In a 25 mL two-necked RBF, 1-bromo-3-(trifluoromethyl)benzene (0.28 g, 1.28 mmol) was dissolved in diethyl ether (3 mL, 10 volumes). The reaction mixture was cooled to -78 to -70°C, and n-butyllithium (1.02 mL, 2.5 M, 2 equivalents) was added to the reaction mixture. The RM was stirred at -78 to 70°C for 1 hour. This lithification solution was used in the reaction with N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (intermediate

[0234] ). In a separate flask, N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (0.1 g, 0.427 mmol), copper dimethyl sulfide complex (4 mg, 0.021 mmol), and (S)-N-((S)-1-(butylamino)-1-oxo-3-phenylpropan-2-yl)-2-(((E)-2-(diphenylphosphanail)benzylidene)amino)-3-methylbutanamide (15 mg, 0.025 mmol) were taken in Et2O (5 mL) and cooled to -78 to 70°C. Lithium-1-bromo-3-(trifluoromethyl)benzene was added to this reaction mixture at -78 to 70°C and stirred for 4 hours. The reaction was monitored by LC-MS and TLC. TLC showed the formation of new spots, and LC-MS showed the presence of the desired mass. The reaction mixture was quenched with an aqueous NH4Cl solution and extracted with ethyl acetate (2 × 25 mL). The combined organic layer was washed with saturated brine and dried over Na2SO4. The organic layer was concentrated under reduced pressure below 45°C to obtain the crude product. The crude product was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent. 30 mg of anti-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide was obtained as a pale yellow solid (18.5% yield and 30.9% purity by LC-MS). LCMS(ES): m / z 381.2 (M+1).

[0506] Preparation Synthesis of (3S,4S)-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide. [ka] In a 25 mL two-necked RBF, 1-bromo-3-(trifluoromethyl)benzene (0.8 g, 3.57 mmol) was dissolved in dry diethyl ether (10 mL, 12.5 vol). The reaction mixture was cooled to -78 to -70°C, and then n-butyllithium (2.8 mL, 2.5 M, 2 equivalents) was added to the reaction mixture. The reaction mixture was stirred at -78 to -70°C for 1 hour. This lithium solution was used in the reaction with N-(2,3-difluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (intermediate

[0252] ).

[0507] In a separate flask, N-(2,3-difluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (0.3 g, 1.19 mmol), copper dimethyl sulfide complex (12 mg, 0.059 mmol), and (S)-N-((S)-1-(butylamino)-1-oxo-3-phenylpropan-2-yl)-2-(((E)-2-(diphenylphosphanail)benzylidene)amino)-3,3-dimethylbutanamide (43 mg, 0.071 mmol) were taken from Et2O (6 mL, 20 volumes). The resulting reaction mixture was cooled to -78 to 70°C, and then lithium-1-bromo-3-(trifluoromethyl)benzene was added at -78 to 70°C. Next, the reaction mixture was stirred at -78 to -70°C for 4 hours, then heated to 20 to 25°C and maintained at 20 to 25°C for 12 hours. The reaction mixture was monitored by TLC and LC-MS. TLC showed the formation of new spots, and similarly, LC-MS showed the formation of the desired mass. The reaction mixture was then quenched with saturated NH4Cl aqueous solution and subsequently extracted with ethyl acetate (3 × 25 mL). The combined ethyl acetate layer was washed with saturated brine solution and dried over Na2SO4. The ethyl acetate was then evaporated under reduced pressure below 45°C to obtain the crude compound. The obtained crude product was then purified by column chromatography using silica gel (60 to 120 mesh) with ethyl acetate / hexane as the eluent. 55 mg of N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide was obtained as a pale yellow solid (11.2% yield by LC-MS, 72.3% purity). LCMS(ES): m / z 399 (M+1).

[0508] Preparation Y Synthesis of N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxopyrrolidine-3-carboxamide using propylphosphonic anhydride (T3P) [ka] 1-Methyl-2-oxopyrrolidine-3-carboxylic acid (5 g, 34.9 mmol) was dissolved in dimethylformamide (20 mL, 4 volumes), cooled to 0°~5°C, and triethylamine (10.5 g, 103.9 mmol), 2,6-difluoropyridine-3-amine (5 g, 38.4 mmol), followed by propylphosphonic anhydride (T3P) (44 g, 138.3 mmol; 50% solution in toluene) were added at 0~5°C. The reaction mixture was stirred at 0~5°C for 2 hours. The reaction mixture was added to water and extracted with ethyl acetate (3 × 100 ml). The combined organic layer was washed with water, followed by brine. The organic matter was dried over sodium sulfate and concentrated to obtain a solid.

[0509] To this solid, 10V n-heptane (10 volumes) was added and stirred for 1 hour. The solid was then filtered and dried under vacuum to obtain 5.5 g of N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxopyrrolidine-3-carboxamide as a grayish-white solid (yield 61.7% and purity 91.6% by LC-MS). 1 H NMR(DMSO-d6):δ 10.30(s,1H),8.60-8.54(m,1H),7.19-7.16(m,1H),3.71-3.67(t,18Hz,1H),3.43-3.32(m,2H),2.89(s,3H),2.31-2.20(m,2H).LCMS(EI):m / z 256.2(M+1).

[0510] Preparation Z Synthesis of N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxo-3-(phenylceranyl)pyrrolidine-3-carboxamide [ka] To a stirred solution of NaH (1.25 g, 52.08 mmol) in THF (10 mL) at 0-5°C, N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxopyrrolidine-3-carboxamide (4 g, 15.68 mmol) was added and dissolved in THF (20 mL). The reaction mixture was stirred at 0-5°C for 20 minutes. Phenylselenyl bromide (4.07 g, 17.25 mmol), dissolved in THF (10 mL) at 0-5°C, was added and stirred for 2 hours. The reaction mixture was quenched in cold water and extracted with ethyl acetate (3 × 50 mL). The combined organic layers were concentrated to obtain the crude compound, which was purified by silica gel column chromatography using ethyl acetate / hexane as the eluent to obtain 4.2 g of N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxo-3-(phenylceranyl)pyrrolidine-3-carboxamide as a pale yellow solid. Yield by LC-MS was 65.6%, purity 99.2%. 1H NMR(DMSO-d6):δ 10.23(brs,1H),8.71-8.64(m,1H),7.59-7.56(m,2H),7.47-7.43(m,1H),7.35-7.31(m,2H),7.19-7.16(m, 1H),3.39-3.28(m,1H),3.24-3.18(m,1H),2.79(s,3H),2.63-2.55(m,1H),2.19-2.14(m,1H).LCMS(EI):m / z 412.2 (M+1).

[0511] Preparation AA Synthesis of N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide: [ka] N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxo-3-(phenylselenyl)pyrrolidine-3-carboxamide (4 g, 9.73 mmol) was dissolved in dichloromethane (40 mL, 10 volumes), and H2O2 (2.2 g, 64.8 mmol; 30% aqueous solution) was added at 0-5°C. The reaction mixture was stirred at 0-5°C for 2 hours. The reaction mixture was quenched in a saturated solution of NaHCO3 at 0-5°C, followed by extraction with dichloromethane (2 × 100 mL). The organic layer was washed with NaHCO3 solution (4 × 50 mL), dried over anhydrous Na2SO4, and concentrated to obtain the crude product. The crude compound was suspended in IPA (5 mL), stirred for 2 hours, filtered, and dried to obtain 1.5 g of N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide as a pale yellow solid with a yield of 62.5% and purity of 91.6% by LC-MS. 1H NMR(CDCl3):δ 11.1(s,1H),8.98-8.92(m,1H),8.0(s,1H),6.83(m,1H)4.13(s,2H),3.15(s,3H).LCMS(EI):m / z 254.2(M+1).

[0512] Preparation AB Synthesis of (3R,4R)-N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxo-4-(4-(trifluoromethyl)phenyl)-pyrrolidine-3-carboxamide: [ka] In a 25 mL two-necked RBF, N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (300 mg, 1.18 mmol) was dissolved in dry diethyl ether (10 mL), and CuBr.SMe2 (12 mg, 0.05 mmol) was added. Subsequently, (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (44 mg, 0.071 mmol) was added at 20-25°C. The reaction mixture was stirred at 20-25°C for 20 minutes. The reaction mixture was cooled to -20--25°C using dry ice / acetonitrile, and trimethylsilyl trifluoromethanesulfonate (0.57 g, 2.6 mmol) was added and stirred for 20 minutes. 4-(trifluoromethyl)phenyl)magnesium bromide (2.2 mL, 1.6 M) was added at -20 to -25°C and stirred for 2 hours. At this point, TLC analysis indicated completion of the reaction (50:50 ethyl acetate:hexane, R f Starting material = 0.3, R f Product = 0.5. The reaction mixture was quenched in NH4Cl aqueous solution (20 mL) and extracted with ethyl acetate (2 × 50 mL). The combined organic layer was washed with saturated brine solution (100 mL), dried over Na2SO4, and concentrated to obtain the crude product. This was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane (20:80) as the eluent, and by chiral HPLC, 120 mg of (3R,4R)-N-(2,6-difluoropyridine-3-yl)-1-methyl-2-oxo-4-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide was obtained as a pale yellow solid (24.6% yield by LCMS, 89.8% purity) with a chiral enantiomer ratio of 47.5:47.8. 1H NMR(CDCl3):δ 10.07(s,1H),8.76-8.69(m,1H)7.66-7.64(m,2H),7.51-7.48(m,2H),6.79-6.76(m,1H),4.16-4.09 (m,1H),3.83-3.79(m,1H),3.65-3.62(d,9.6Hz,1H),3.50-3.56(m,1H),3.07(s,3H).LCMS(ES):m / z 400.3(M+1).

[0513] Preparation AC Synthesis of 1-benzyl-N-(2-fluorophenyl)-2-oxopyrrolidine-3-carboxamide using propylphosphonic anhydride (T3P). [ka] 1-Benzyl-2-oxopyrrolidine-3-carboxylic acid (3 g, 13.69 mmol) (see International Publication No. 2010 / 142801) was dissolved in dimethylformamide (15 mL, 5 volumes), cooled to 0°~5°C, and triethylamine (4.15 g, 41.0 mmol), 2-fluoroaniline (1.67 g, 15.06 mmol), followed by propylphosphonic anhydride (T3P) (8.7 g, 27.36 mmol; 50% solution in ethyl acetate) were added at 0~5°C. The reaction mixture was stirred at 0~5°C for 2 hours. The reaction mixture was added to water and extracted with ethyl acetate (2 × 100 ml). The combined organic layer was then diluted with water, followed by a bleaching agent. The sample was washed with a solution, dried over sodium sulfate, and concentrated to obtain a solid. To this solid, heptane (10 volumes) was added, the mixture was stirred for 1 hour, filtered, and dried under vacuum to obtain 4.0 g of 1-benzyl-N-(2-fluorophenyl)-2-oxopyrrolidine-3-carboxamide as a grayish-white solid. Yield was 95.2% and purity 94.6% by LC-MS. 1H NMR(DMSO-d6):δ 10.12(s,1H),8.06-8.01(m,1H),7.37-7.30(m,2H),7.28-7.24(m,4H),7.20-7.14(m,2H), 4.44(s,2H),3.85-3.81(t,J=8Hz,1H),3.36-3.22(m,2H),2.31-2.22(m,2H).LCMS(EI):m / z 313.3(M+1).

[0514] Preparation AD Synthesis of 1-benzyl-N-(2-fluorophenyl)-2-oxo-3-(phenylceranyl)pyrrolidine-3-carboxamide: [ka] To a stirred solution of NaH (974 mg, 40.59 mmol) in THF (10 mL) at 0-5°C, 1-benzyl-N-(2-fluorophenyl)-2-oxopyrrolidine-3-carboxamide (3.8 g, 12.17 mmol) dissolved in THF (20 mL, 5.2 vol) was added. The reaction mixture was stirred at 0-5°C for 20 minutes. Phenylselenyl bromide (3.16 g, 13.39 mmol) dissolved in THF (10 mL) at 0-5°C was added, and the mixture was stirred for 2 hours. The reaction mixture was quenched in cold water and extracted with ethyl acetate (3 × 50 mL). The combined organic layers were concentrated to obtain the crude compound, which was purified by silica gel column chromatography using ethyl acetate / hexane as the eluent to obtain 5.1 g of 1-benzyl-N-(2-fluorophenyl)-2-oxo-3-(phenylselenyl)pyrrolidine-3-carboxamide as a pale yellow solid (yield 89.4% by LCMS, purity 98.6%). 1H NMR (DMSO-d6): δ 10.12(brs,1H),8.33-8.29(t,J=8Hz,1H),7.61-7.59(m,2H),7.40-7.30(m,8H),7.12-7.10(m,3H),4.56- 4.41(dd,2H),3.26-3.12(m,2H),2.68-2.60(m,1H),2.28-2.22(m,1H). LCMS(EI): m / z 469.3 (M+1).

[0515] Preparation AE Synthesis of 1-benzyl-N-(2-fluorophenyl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide: [ka] 1-Benzyl-N-(2-fluorophenyl)-2-oxo-3-(phenylceranyl)pyrrolidine-3-carboxamide (5 g, 10.68 mmol) was dissolved in dichloromethane (50 mL, 10 volumes), and H2O2 (2.4 g, 71.22 mmol; 30% solution) was added at 0-5°C. The reaction mixture was stirred at 0-5°C for 2 hours. The reaction mixture was quenched in ice-cold saturated NaHCO3 solution and extracted with dichloromethane (3 × 100 mL). The organic layer was washed with NaHCO3 solution (2 × 100 mL), dried under Na2SO4, and concentrated to produce the crude product. The substance was obtained. The crude compound was suspended in IPA (10 mL, 2 volumes), stirred for 2 hours, filtered, and dried to obtain 2.2 g of 1-benzyl-N-(2-fluorophenyl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide as a grayish-white solid. Yield was 66.6% and purity 94.4% by LC-MS. LCMS(EI): m / z 311.2 (M+1).

[0516] Adjusted AF Synthesis of (3S,4S)-1-benzyl-N-(2-fluorophenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide [ka] In a 25 mL two-necked RBF, 1-benzyl-N-(2-fluorophenyl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (300 mg, 0.96 mmol) was dissolved in dry diethyl ether (9 ml), and CuBr.SMe2 (mg, mmol), followed by (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (10 mg, 0.04 mmol), was added at 20-25°C. The reaction mixture was stirred at 20-25°C for 20 minutes. The reaction mixture was cooled to -20--25°C using dry ice / acetonitrile, and trimethylsilyl trifluoromethanesulfonate (0.46 g, 2.1 mmol) was added and stirred for 20 minutes. At -20 to -25°C, (3-(trifluoromethyl)phenyl)magnesium bromide (1.8 mL, 1.6 M) was added and stirred for 2 hours. The reaction mixture was quenched in NH4Cl aqueous solution (20 mL) and extracted with ethyl acetate (2 × 50 mL). The combined organic layers were washed with saturated brine solution (100 mL), dried over Na2SO4, and concentrated to obtain the crude product. This was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent to obtain 50 mg of 1-benzyl-N-(2-fluorophenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as an oily liquid. Yield of 16.6% and purity of 42.5% by LC-MS. 1H NMR(DMSO-d6):δ 10.15(s,1H),8.0-7.97(m,1H)7.69(s,1H),7.65-7.56(m,3H),7.39-7.35(m,2H),7.32-7.30(m,4H),7.29-7.24(m, 2H),4.54-4.42(m,2H),4.19-4.17(m,1H),4.10-4.08(q,J=8Hz,1H),3.80--3.75(t,J=12Hz,1H),3.48-3.46(m,1H). LCMS(ES): m / z 457.3 (M+1).

[0517] preparation ag Synthesis of (3S,4R)-N-(2,3-difluorophenyl)-1-methyl-4-(1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-2-oxopyrrolidine-3-carboxamide [ka] In a 25 mL two-necked RBF, 3-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole (810 mg, 3.57 mmol) was dissolved in dried diethyl ether (10 mL). It was dissolved in L (12.5 vol). The reaction mixture was cooled to -78 to -70°C, and n-butyllithium (4.28 mL, 2.5 M, 3.0 equivalents) was added to the reaction mixture. The reaction mixture was stirred at -78 to 70°C for 1 hour. In a separate flask, N-(2,3-difluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (300 mg, 1.19 mmol), copper(I) bromide dimethyl sulfide complex (12 mg, 0.059 mmol), and 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (44 mg, 0.071 mmol) were taken from dry diethyl ether (9 mL, 30 vol), and the reaction mixture was cooled to -78 to 70°C. Lithium-conjugated N-(2,3-difluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide was added dropwise to this RM at -78 to 70°C and stirred for 1 hour. The reaction mixture was quenched in an aqueous NH4Cl solution and extracted with ethyl acetate (2 × 25 mL). The combined organic layers were washed with saturated brine, dried over Na2SO4, and concentrated to obtain the crude product. This was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent, yielding 30 mg of (3S,4R)-N-(2,3-difluorophenyl)-1-methyl-4-(1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-2-oxopyrrolidine-3-carboxamide as a colorless liquid along with its enantiomer. Yield by LCMS was 6%, purity 43.2%. LCMS(ES): m / z 403.3 (M+1).

[0518] Preparation AH Synthesis of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide using (CuOTf)2.C6H6 N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (500 mg, 2.13 mmol) was dissolved in dry diethyl ether (20 mL, 4 volumes), and copper(I) bromide dimethyl sulfide complex (22 mg, 0.1 mmol) and (S)-N-((S)-1-(butylamino)-1-oxo-3-phenylpropan-2-yl)-2-(((E)-2-(diphenylphosphanail)benzylidene)amino)-3-methylbutanamide (76 mg, 0.12 mmol) were added at 20-25°C and stirred for 20 minutes at 20-25°C. The reaction mixture was cooled to -17-23°C, trimethylsilyl trifluoromethanesulfonate (1 g, 4.68 mmol) was added and stirred for 10 minutes. 7.9 mL, 0.8 M, 3.0 equivalents of magnesium 3-(trifluoromethyl)phenyl) bromide were added at -17 to -23°C and stirred for 2 hours. The reaction mixture was quenched in an aqueous NH4Cl solution and extracted with ethyl acetate (2 × 25 mL). The combined organic layers were washed with saturated brine, dried over Na2SO4, and concentrated to obtain 960 mg of crude (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as a colorless liquid with a chiral enantiomer ratio of 1:1.43 (excess S,S enantiomer) according to chiral HPLC. [ka]

[0519] Preparation AI Synthesis of 1-methylpiperidine-2-one [ka] Sodium hydride (9.0 g, 378.7 mmol) was taken from THF (50 mL, 5.5 vol) at 0-5°C, piperidine-2-one (25 g, 252.5 mmol) was added, and dissolved in THF (50 mL, 10 vol). After stirring for 30 minutes, methyl iodide (89.5 g, 631.3 mmol) was added dropwise to the reaction mixture. The reaction mixture was slowly heated to 20-25°C and stirred for 6 hours. The reaction mixture was quenched in dilute HCl and extracted with 10% MeOH:DCM (2 × 250 mL). The combined organic layers were dried in sodium sulfate and concentrated to obtain the crude compound, which was purified by silica gel column chromatography using ethyl acetate / hexane as the eluent to obtain 27.0 g of 1-methylpiperidine-2-one as a colorless liquid (yield 94.7%, purity 94.5% by LCMS). 1H NMR (DMSO-d6): δ 3.23-3.20(m,1H),2.78(s,3H),2.18-2.15(t,Jis 12Hz,2H),1.73-1.65(m,4H). LCMS(EI): m / z 114.0 (M+1).

[0520] Preparation AJ Synthesis of 1-methyl-2-oxopiperidine-3-carboxylic acid: [ka] Sodium hydride (5.3 g, 221.23 mmol) was taken from THF (50 mL, 9.4 vol) at 0-5°C, 1-methylpiperidine-2-one (5 g, 44.24 mmol) was added, and dissolved in THF (25 mL, 5 vol). The reaction mixture was heated to 60-65°C and stirred at this temperature for 1 hour. After stirring for 1 hour, diethyl carbonate (31.3 g, 265.26 mmol) was added dropwise to the reaction mixture and stirred at 60-65°C for 12 hours. The reaction mixture was quenched in cold water and extracted with 2-MeTHF. The aqueous layer was acidified with HCl and extracted with 10% IPA:DCM (5 × 50 mL). The combined organic layers were dried under Na2SO4 and concentrated to obtain the crude product. The crude compound was suspended in IPA (5 volumes), stirred for 2 hours, filtered, and dried to obtain 4.7 g of 1-methyl-2-oxopiperidine-3-carboxylic acid as a grayish-white solid. Yield was 68.1% and purity 94.7% by LC-MS. 1H NMR (DMSO-d6): δ 12.56(s,1H),3.33-3.20(m,3H),2.82(s,3H),1.99-1.90(m,1H),1.88-1.69(m,3H). LCMS(EI): m / z 158.1 (M+1).

[0521] Preparation AK Synthesis of N-(2,3-difluorophenyl)-1-methyl-2-oxopiperidine-3-carboxamide [ka] 1-Methyl-2-oxopiperidine-3-carboxylic acid (4g, 25.4 mmol) The mixture was dissolved in methylformamide (20 ml, 5 volumes), cooled to 0°~5°C, and triethylamine (7.7 g, 76.4 mmol), 2,3-difluoroaniline (3.6 g, 28.0 mmol), followed by T3P (32.4 g, 101.9 mmol; 50% solution in ethyl acetate) was added at 0°~5°C. The reaction mixture was stirred at 0~5°C for 2 hours. The reaction mixture was added to water and extracted with ethyl acetate (2 × 50 ml). The combined organic layer was washed with water, followed by brine solution, dried over sodium sulfate, and concentrated to obtain a solid. Solid heptane (10 volumes) was added to this, stirred for 1 hour, filtered, and dried under vacuum to obtain 2.1 g of N-(2,3-difluorophenyl)-1-methyl-2-oxopiperidine-3-carboxamide as a grayish-white solid. Yield of 29.4% and purity of 92.2% by LC-MS. 1H NMR(DMSO-d6):δ 10.29(s,1H),7.83-7.7.78(m,1H),7.20-7.13(m,2H),3.62-3.58(t,16Hz,1H),3.37-3.25 (m,2H),2.89(s,3H),2.05-2.0(m,2H),1.99-1.85(m,1H),1.76-1.70(m,1H).LCMS(EI):m / z 269.2(M+1).

[0522] Preparation AL Synthesis of N-(2,3-difluorophenyl)-1-methyl-2-oxo-3-(phenylselenyl)piperidine-3-carboxamide [ka] N-(2,3-difluorophenyl)-1-methyl-2-oxopiperidine-3-carboxamide (2 g, 7.46 mmol) was dissolved in THF (20 ml, 10 volumes), and NaH (0.89 g, 37.3 mmol) was added at 0-5°C. The reaction mixture was stirred at 0-5°C for 30 minutes. Phenylselenyl bromide (1.76 g, 7.46 mmol) dissolved in THF (5 mL) at 0-5°C was added, and the mixture was stirred for 2 hours. The reaction mixture was quenched in cold water and extracted with ethyl acetate (2 × 50 mL). The combined organic layers were concentrated to obtain the crude compound, which was purified by silica gel column chromatography using ethyl acetate / hexane as the eluent to obtain 2.6 g of N-(2,3-difluorophenyl)-1-methyl-2-oxo-3-(phenylselenyl)piperidine-3-carboxamide as a pale yellow solid. Yield of 83.8% and purity of 93.1% by LC-MS. 1H NMR(DMSO-d6):δ 10.94(s,1H),7.98-7.94(m,1H),7.53-7.51(m,2H),7.45-7.41(m,1H),7.34-7.31(m,2H),7.19-7. 11(m,2H),3.40-3.31(m,2H),2.93(s,3H),2.23-2.17(m,1H),2.19-1.88(m,2H),1.67-1.64(m,1H). LCMS(EI): m / z 425.2 (M+1).

[0523] Preparation AM Synthesis of N-(2,3-difluorophenyl)-1-methyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide [ka] N-(2,3-difluorophenyl)-1-methyl-2-oxo-3-(phenyl selenium) Nyl)piperidine-3-carboxamide (2.5 g, 5.89 mmol) was dissolved in MDC (25 ml, 10 volumes), and H2O2 (1.3 g, 39.30 mmol; 30% solution) was added at 0-5°C. The reaction mixture was stirred at 0-5°C for 2 hours. The reaction mixture was quenched in ice-cold saturated NaHCO3 solution and extracted with dichloromethane (2 × 50 mL). The organic layer was washed with NaHCO3 solution (3 × 20 mL), dried under Na2SO4, and concentrated to obtain the crude product. The crude compound was suspended in IPA (5 mL), stirred for 2 hours, filtered, and dried to obtain 1.2 g of N-(2,3-difluorophenyl)-1-methyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide as a pale yellow solid with a yield of 80% and purity of 98.3% by LC-MS. 1H NMR(DMSO-d6):δ 12.32(s,1H),8.18-8.13(m,1H),7.86-7.84(t,Jis8Hz,1H)7.23-7.11(m,2H),3.53-3.49(t,Jis16Hz,2H),2.99(s,3H),2.66-2.61(m,2H). LCMS(EI): m / z 267.2 (M+1).

[0524] Preparation AN Synthesis of anti-N-(2,3-difluorophenyl)-4-(4-fluorophenyl)-1-methyl-2-oxopiperidine-3-carboxamide [ka] In a 25 mL two-necked RBF, 1-bromo-4-fluorobenzene (530 mg, 3.0 mmol) was dissolved in dry THF (6 mL, 11 vol). The reaction mixture was cooled to -78 to -70°C, and n-butyllithium (1.8 mL, 2.5 M, 1.5 equivalents) was added to the reaction mixture. The reaction mixture was stirred at -78 to 70°C for 1 hour. In a separate flask, N-(2,3-difluorophenyl)-1-methyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carboxamide (250 mg, 0.93 mmol), copper(I) bromide dimethyl sulfide complex (9 mg, 0.046 mmol), and 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (35 mg, 0.056 mmol) were taken from THF (5 mL, 20 volumes), and the reaction mixture was cooled to -78 to 70°C. Lithium-ionized 1-bromo-4-fluorobenzene was added dropwise to this RM at -78 to 70°C, and the mixture was stirred for 1 hour. The reaction mixture was quenched in aqueous NH4Cl solution and extracted with ethyl acetate (2 × 50 mL). The combined organic layers were washed with saturated brine, dried over Na2SO4, and concentrated to obtain the crude product. This crude product was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane as the eluent to obtain 40 mg of anti-N-(2,3-difluorophenyl)-4-(4-fluorophenyl)-1-methyl-2-oxopiperidine-3-carboxamide as a grayish-white solid. The yield by LC-MS was 11.7%, with a purity of approximately 90%. 1H NMR (DMSO-d6): δ 9.91(s,1H),7.54-7.50(m,1H),7.32-7.29(m,2H),7.14-7.06(m,4H),3.84- 3.81(d,1H),3.55-3.42(m,3H),2.96(s,3H),2.07-1.96(m,2H). LCMS(ES): m / z 363.3 (M+1).

[0525] Preparation ANa (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxyl ether is used as a solvent in methyl tert-butyl ether. Synthesis of thamide. [ka] In a 25 mL flask A, (R)-(+)-1,1'-Bi(2-naphthol) (91 mg, 0.320 mmol) was added to 2 mL of anhydrous methyl tert-butyl ether at 20-25°C and stirred for 50 minutes. In flask B, magnesium (3-(trifluoromethyl)phenyl)bromide (5.3 mL, 4.26 mmol, 0.8 M in Et2O) was slowly added to bis-[2-(N,N-dimethylaminoethyl ether (683 mg, 4.27 mmol) in 3 mL of dry methyl tert-butyl ether under nitrogen at 0-5°C, and then stirred for 30 minutes. Next, mixture A was introduced into mixture B at 0-5°C. Then, RM was heated to 20-25°C and stirred for 1 hour. Next, RM was cooled to 0-5°C, and N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide (500 mg, 2.13 mmol) in methyl tert-butyl ether (5 mL) was added dropwise. The mixture was heated to 20-25°C and stirred for 12 hours. The reaction product was 10% The mixture was quenched with an aqueous HCl solution and extracted with ethyl acetate (25 mL x 2). The combined organic layer was dried over anhydrous Na2SO4 and evaporated under vacuum to obtain 800 mg of crude product. The crude product was purified by column chromatography using silica gel (60-120 mesh) with ethyl acetate / hexane (20:80) as the eluent, and 50 mg of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide with a chiral enantiomer ratio of 1:2 (R,R enantiomer:S,S enantiomer) was obtained by chiral HPLC. LCMS(ES): m / z 381.2 (M+1).

[0526] Preparation AO Synthesis of N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylthio)-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide To a stirred solution of NaH (0.94 g, 39.47 mmol) in THF (10 mL) at 0-5°C, N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide (1.5 g, 3.94 mmol) in THF (10 mL) was added. The reaction mixture was stirred at 0-5°C for 20 minutes. THF (10 mL) containing diphenyl disulfide (1.29 g, 5.92 mmol) was added at 0-5°C. The reaction mixture was stirred at 20-25°C for 48 hours. The reaction mixture was quenched in cold water and extracted with ethyl acetate (3 × 50 mL). The combined organic layers were concentrated to obtain the crude compound, which was purified by silica gel column chromatography using ethyl acetate / hexane as the eluent. This yielded 1.5 g of N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylthio)-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide as a grayish-white solid. The yield by LC-MS was 78.9%, and the purity was 96.6%. 1H NMR(DMSO-d6):δ 10.28(s,1H),7.68-7.64(m,1H),7.57-7.55(m,1H),7.52-7.42(m,5H),7.38-7.32(m,1 H),7.19-7.02(m,2H),4.05-3.97(m,2H),3.37-3.33(m,1H),2.91(s,3H).LCMS(EI):m / z 489.3(M+1).

[0527] Preparation AP N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluorophenyl) Synthesis of thiophenyl-2,5-dihydro-1H-pyrrole-3-carboxamide [ka] N-(2-fluorophenyl)-1-methyl-2-oxo-3-(phenylthio)-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxamide (1.5 g, 3.07 mmol) was dissolved in dichloromethane (15 mL, 10 volumes), and m-CPBA (1.05 g, 6.14 mmol) was added at 20-25°C. The reaction mixture was stirred at 20-25°C for 4 hours. The reaction mixture was quenched in ice-cold saturated NaHCO3 solution and extracted with dichloromethane (2 × 50 mL). The organic layer was washed with NaHCO3 solution (2 × 50 mL), dried under Na2SO4, and concentrated to obtain a solid. The solid was suspended in heptane (10 mL), stirred for 2 hours, filtered, and dried to obtain 600 mg of N-(2-fluorophenyl)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)-2,5-dihydro-1H-pyrrole-3-carboxamide as a grayish-white solid (54.5% yield and 82.8% purity by LC-MS). 1H NMR(CDCl3):δ 11.52(s,1H),8.40-8.36(m,1H),7.92-7.90(m,1H),7.79(s,1H),7.73-7.71(m,1 H),7.61-7.57(m,1H),7.14-7.04(m,3H),4.33(s,2H),3.21(s,3H).LCMS(EI):m / z 379.2(M+1).

[0528] It is recognized by those skilled in the art that various functional groups can be converted to other functional groups to provide different saturated target compounds encompassed by the general formula 1 defined above. For a valuable resource describing the interconversion of functional groups in a simple and direct manner, see Larock, RC, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999.

[0529] It is recognized that some of the reagents and reaction conditions described above for preparing saturated target compounds and corresponding novel and present-inventive intermediates may not be compatible with certain functional groups present in the present-inventive intermediates from which they are prepared. In these cases, incorporating protecting / deprotecting sequences or functional group interconversions into the synthesis can help obtain the desired product. The use and selection of protecting groups will be obvious to those skilled in the art of chemical synthesis (see, for example, Greene, TW; Wuts, PGMP Rotective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991).

[0530] Those skilled in the art will recognize that, in some cases, after introducing a given reagent as illustrated in any individual scheme, it may be necessary to carry out further routine synthetic steps not detailed herein to complete the synthesis of the saturated target compound encompassed in General Formula 1 as defined above and the novel and inventive intermediates detailed herein. Those skilled in the art will also recognize that it may be necessary to carry out combinations of steps shown in the above schemes in an order other than that implied by the specific schemes illustrated to prepare compounds containing the saturated target compound.

[0531] Those skilled in the art will also know that saturated target compounds, including compounds encompassed by general formulas II, III, IV, and D as described and defined herein, as well as the intermediates, impurities, markers, and degradable compounds of the present invention, can be subjected to various electrophilic reactions to add substituents or modify existing substituents. It will be recognized that it can be used in nucleophilic reactions, radical reactions, organometallic reactions, oxidation reactions, and reduction reactions.

[0532] Without further detail, it is expected that those skilled in the art using this disclosed description will be able to make the most of the present invention. Accordingly, the above examples, embodiments, and process descriptions should be construed as merely illustrative and not to limit the present disclosure.

[0533] The inventors assert that all embodiments of the invention are protected, and make it clear that if an unimplementable embodiment is inadvertently included in the broad description or definition, all unimplementable embodiments are expressly and unconditionally excluded from the claims for protection. In other words, unimplementable embodiments are, by definition, outside the scope of the protection sought.

[0534] The inventors claim protection for all novel and non-obvious embodiments of the invention, and clarify that if non-novel embodiments are unintentionally included within the broad description or definition, all such anticipated embodiments are excluded from the claims for protection. In other words, if an embodiment comprising several compounds is determined by examination to include an expected member of the group of components to be included, then, by definition, the inventors did not intend to include it, and the compound is outside the scope of the requested protection and has always been outside the scope of protection. Errors in inadvertently including an expected compound in a broad compound list due to texture inaccuracy should be rectified by removing the erroneous group member without affecting the rest of the compounds in that list or group.

Claims

1. Process B1 for preparing a saturated target of Equation 1 from an unsaturated precursor of Equation 2, the following scheme: 【Chemistry 1】 The formula includes Grignard reagents, organolithium reagents, organozinc reagents, and substitutions of 1,4 systems exemplified by hydrogenation, hydride sources, electron sources (reduction exemplified by Zn / AcOH), or 1,4-addition using enzymes, wherein, R β A α A β nα, Q α and R ε Each of these has the same meaning as defined in compound A2, R α is an ester containing aliphatic and aromatic esters exemplified by H, halogen or substituted or unsubstituted alkyl, aryl, heterocyclic, naphthyl, C(O)OC ６ H ５ , -C(O)OC ６ H ４ F, amides containing aliphatic and aromatic exemplified by -C(O)NH C ６ H ５ ), hydrazine amides containing aliphatic and aromatic exemplified by -C(O)NHNH C ６ H ５ ), carbon-containing groups exemplified by thioesters, thionoesters, and, - C(O)NHOC ６ F ５ ); and -C(S)SC ６ H ５ Similar compounds as exemplified by ) etc. R α Since it is not bonded to the ring via an O or N atom, for example, R α Whenever H is added to the 4th position of the 1,4 system, R α It is not H, R γ H, or a substituted or unsubstituted alkyl, aryl, naphthyl, or other carbon-containing group, R δ The process is characterized by H, or a carbon-containing group such as a substituted or unsubstituted alkyl, aryl, or naphthyl atom.

2. Process B1; B1b; B1c; B1d; B2; B2a; B3; B3a; B4; B5; B6; B6a; B7; B8; B9; B10; B11; B12; B13; B14; B15; B16; ;B16b;B16c;B16d;B17;B18;B18a;B18b;B18c;B18d;B19;B19a;B19b;B19c;B20;B21a;B21b;B21c;B22;B A process defined in any one of 23; B24; B25; B26; B27a; B27b; B28a; B28b; B29a; B29b; B30a; B30b; B31; B32; B33; B34; B35; B36; B37; B38; B39; B40; B41; B42; B43; B44; B45; B46; B47; B48; B49; B50; and B51, or selected from the following: a) A process B1b for preparing a saturated target of formula 1 from an unsaturated precursor of formula 2, 【Chemistry 2】 This includes Grignard reagents, organolithium reagents, organozinc reagents, hydrogenation, hydride sources, electron sources, reduction as exemplified by Zn / AcOH, or 1,4-addition using enzymes, and substitution of 1,4 systems. R β A α A β nα, Q α and R ε Each of these has the same meaning as defined in compound A2, R α This includes esters containing H, halogens, or substituted or unsubstituted alkyl, aryl, heterocyclic, naphthyl, aliphatic, and aromatic esters, such as C(O)OC. ６ H ５ , or -C(O)OC ６ H ４ F) Amides containing aliphatic and aromatic compounds, e.g., -C(O)NHC ６ H ５ ), aliphatic and aromatic hydrazine amides, e.g., -C(O)NHNHC ６ H ５ ), thioesters, thionoesters, and -C(O)NHOC ６ F ５ ); -C(S)SC ６ H ５ A carbon-containing group, as exemplified by similar compounds such as ) R γ H, or a substituted or unsubstituted alkyl, aryl, naphthyl, or other carbon-containing group, R δ H is a carbon-containing group such as a substituted or unsubstituted alkyl, aryl, or naphthyl group, however, R α Since it is not bonded to the ring via an O or N atom, for example, R α It is not -OMe, but whenever H is added to the 4th position of the 1,4 system, A α Except when R is N(Me), α It's R, not H. β If it is m-(trifluoromethyl)benzene, m-(trifluoromethyl)benzene, or 6-(trifluoromethyl)pyridine-3-yl, then R α H can be as shown in the following scheme: 【Transformation 3】 ,process; b) A process B1c for preparing a saturated target from a corresponding unsaturated precursor described in either process B1 or B1b, comprising the unsaturated precursor, a nucleophile exemplified by a Grignard reagent, an organolithium reagent, an organozinc reagent, a hydrogen source, e.g., H ２ The process involves using a combination of an electron source exemplified by / Pd / C, or a hydride source, or Zn / AcOH, and at least one solvent to carry out a 1,4-system substitution, e.g., a 1,4-addition reaction, on the unsaturated precursor to obtain a saturated target as defined by the following formula: 【Chemistry 4】 Preferably, depending on the reaction conditions, the isomers are exemplified by trans or cis isomers. Process where one or more sexes are in excess: 【Transformation 5】 c) A process B1d for preparing a saturated target from a corresponding unsaturated precursor, comprising substituting the unsaturated precursor 1,4 system, for example by 1,4-addition, using a Grignard reagent, an organolithium reagent, an organozinc reagent, hydrogenation, or a hydrogenation source, wherein the resulting saturated target product has an excess of one or more possible isomers, and the process is 【Transformation 6】 【Transformation 7】 【Transformation 8】 A process represented by a scheme selected from a group of related combinations thereof. ； d) Process B2 as described in any one process selected from B1 and B1b, comprising an unsaturated precursor, a nucleophile exemplified by a Grignard reagent, an organolithium reagent, an organozinc reagent, H ２ A process comprising obtaining a saturated target by performing a 1,4-system substitution of the unsaturated precursor, such as a 1,4-addition reaction, using a combination of a hydrogen source or hydride source such as Pd / C, or an electron source such as Zn / AcOH, and a solvent. e) Process B2a for preparing a saturated target of formula 1 from an unsaturated precursor of formula 2, 【Chemistry 9】 This includes Grignard reagents, organolithium reagents, organozinc reagents, and 1,4-system substitutions such as 1,4-addition using hydrogenation or hydride sources. The saturated target product has an excess of one or more possible isomers, R α , R β A α A β nα, Q α and R ε Each of these has the same meaning as defined for compound A2, R γ H or R α And, R δ H or R α The process; f) A process B3 according to either process B2 or process B2a, comprising combining one or more catalytic components selected from an unsaturated precursor, a nucleophile such as a Grignard reagent, an organolithium reagent, an organozinc reagent, or a hydride source, a solvent, and a catalyst; and performing a 1,4-system substitution of the unsaturated precursor, such as a 1,4-addition reaction, to obtain a saturated target; g) A process B3a according to either process B2 or process B2a, comprising combining one or more catalytic components selected from an unsaturated precursor, a nucleophile such as a Grignard reagent, an organolithium reagent, an organozinc reagent, or a hydride source, a solvent, and a catalyst; and performing a 1,4-system substitution of the unsaturated precursor, such as a 1,4-addition reaction, to obtain a saturated target, wherein the saturated target product has an excess of one or more of the possible isomers; h) Process B4 according to any one of processes B2; B2a; B3; B3a, comprising including in any of the following schemes or any combination thereof an additive in the combination which is a source of a reversibly bonded adduct to the unsaturated precursor, such as a Lewis acid, to provide an improvement in the 1,4-addition reaction to the unsaturated precursor for obtaining a saturated target, wherein RGA is a reversibly bonded adduct, 【Chemistry 10】 The improvements provided protect a portion of the unsaturated precursor from undesirable reactions. ; Increasing pathway selectivity; Increasing selectivity for a specific desired isomer; Increasing the reactivity of the unsaturated precursor; and R such as Grignard reagents required δ It is either enabling a reduction in the amount of the supply source, R α , R β , R γ A α A β nα, Q α And R ε and R δ This has the same meaning as any one of the processes B1; B1a; B1b; B2 and B2a; i) Process B5, defined as any one of processes B2; B2a; B3; B3a; and B4, further comprising the step of purifying the obtained saturated target product; j) Process B6 according to any one of processes B2; B2a; B3; B3a; B4; and B5, further comprising the step of crystallizing the obtained saturated target product; k) A process B6a described in any one of processes B2; B2a; B3; B3a; B4; and B5, further comprising the step of obtaining an amorphous solid saturated target product by subjecting the saturated target obtained by any one of processes B2; B2a; B3; B3a; B4 to a process such as spray drying, freeze-drying, or adsorption of a solution of the saturated target onto a solid carrier material; l) A process B7 according to any one of processes B2 to B6, further comprising the steps of: performing a 1,4-addition reaction to obtain a saturated target by combining an unsaturated precursor, a nucleophile such as a Grignard reagent, an organolithium reagent, an organozinc reagent, or a hydride source, a solvent; a catalyst; a pre-catalyst; a co-catalyst, and an additive which is a source of reversibly bonded adducts; purifying and crystallizing the reaction product to obtain a crystalline purified saturated target product; m) Process B8 B7 wherein the combination step comprises a Grignard reagent; an organolithium reagent, an organozinc reagent, or a hydride source, together with a solvent such as diethyl ether, and two or more catalyst components selected from a catalyst; a pre-catalyst; a co-catalyst, and a mixture thereof, and a Lewis acid; n) Process B9 according to any one of processes B1 to B8, wherein the unsaturated precursor is dissolved in a solvent such as diethyl ether, and preferably, for example, both CuBr. SMe ２ (Copper(I) bromide dimethyl sulfide complex) and Adding catalyst components including one or more catalysts such as R-BINAP or a combination of (S)-N-((S)-1-(butylamino)-1-oxo-3-phenylpropan-2-yl)-2-(((E)-2-(diphenylphosphanail)benzylidene)amino)-3-methylbutanamide; a pre-catalyst; and a co-catalyst, 【Chemistry 11】 For example, stirring the reaction mixture by stirring or mixing in a continuous reactor, and optionally adding a Lewis acid, such as trimethylsilyl chloride, which is a reversibly bonded adduct to the unsaturated precursor; continuing stirring for an appropriate time, such as about 20 minutes, and adjusting the temperature to an optimal level, preferably a low temperature such as -20°C to -25°C; adding a nucleophile such as a Grignard reagent, or a hydride source, and stirring for a certain period of time to achieve the optimal product by balancing parameters such as the desired quality and acceptable yield within a reasonable reaction time; and for example, NH ４ Quenching the reaction mass in an aqueous Cl solution, optionally extracting it with a suitable solvent, optionally washing the combined organic layer with, for example, a saturated brine solution, and optionally, Na ２ SO ４ A process comprising drying and optionally concentrating to obtain the saturated target product; o) The process according to process B9, further comprising the step of purifying the obtained saturated target product. B10; p) Process B11 according to either one of processes B9 and B10, further comprising the step of crystallizing the obtained saturated target product; q) Process B12 described in Process B1, In the first container A, an unsaturated precursor is dissolved in a solvent such as diethyl ether and stirred. Optionally, the reaction mixture is cooled to a suitable temperature such as 20°C to -25°C, a Lewis acid such as trimethylsilyl chloride is added, and the mixture is stirred. In the second container B, one or more catalysts; a pre-catalyst; and both CuBr. SMe ２ A step of introducing catalyst components including a co-catalyst such as a combination of (copper(I) bromide dimethyl sulfide complex) and R-BINAP, 【Chemistry 12】 The process involves adding a nucleophilic component, such as a Grignard reagent, an organolithium reagent, an organozinc reagent, or a hydride source, to container B, stirring, adding the contents of container A to container B, stirring the mixture for a time such as 20 minutes, and then mixing the reaction mixture with water (NH4H ４ The process involves quenching in a Cl solution and optionally extracting with a solvent, and optionally washing the combined organic layer with, for example, a saturated brine solution, and optionally adding, for example, Na ２ SO ４ A process comprising drying and optionally concentrating to obtain the saturated target product; r) Process B13 according to Process B12, further comprising the step of purifying the obtained saturated target; s) Process B14 according to either one of Process B12 and B13, further comprising the step of crystallizing the obtained saturated target product; t) Process B15 according to any one of Processes B1 to B14, wherein the unsaturated precursor is one of compounds A1 to A35, and includes substitution of the unsaturated precursor with a 1,4 system, such as 1,4-addition using a Grignard reagent, organolithium reagent, organozinc reagent, or hydride source; u) Process B16 described in any one of processes B1 to B15, wherein the unsaturated precursor is the following scheme 【Chemistry 13】 Compound A10 is represented by, The markers that can be formed by the above scheme have the following structure 【Chemistry 14】 This can include one, some, or all of the following: A process comprising substitution of the unsaturated precursor 1,4 system, such as 1,4-addition, using a Grignard reagent or / or an organolithium reagent such as (3-(trifluoromethyl)phenyl)lithium; v) Process B16a described in any one of processes B1 to B15, the same as above The saturated precursor is as follows: 【Chemistry 15】 Compound A10 is represented by the following: 3-(trifluoromethyl)phenylmagnesium bromide, or A process including substitution of the unsaturated precursor 1,4 system, such as 1,4-addition using a Grignard reagent such as 3-(trifluoromethyl)phenyl]magnesium chloride; w) Process B16b described in any one of processes B1 to B15, wherein the unsaturated precursor is the following scheme 【Chemistry 16】 Compound A10 is represented by the following: A process comprising substitution of the unsaturated precursor 1,4 system by 1,4-addition or the like using an organolithium reagent such as 3-(trifluoromethyl)phenyllithium; x) Process B16c described in any one of processes B1 to B15, wherein the unsaturated precursor is the following scheme 【Chemistry 17】 Compound A10 is represented by the following: A process including substitution of unsaturated precursor 1,4 systems by 1,4-addition using organozinc reagents such as 3-(trifluoromethyl)phenylzinc(II) bromide; y) Process B16d described in any one of processes B1 to B15, wherein the unsaturated precursor is the following scheme [Chemistry 18] Compound A10 is represented by the following: The marker that can be formed by the above scheme has the following structure 【Chemistry 19】 This can include one, some, or all of the following: A process comprising substitution of an unsaturated precursor 1,4 system by 1,4-addition using a Grignard reagent or / or an organolithium reagent, such as (3-(trifluoromethyl)phenyl)lithium; z) The following scheme 【Chemistry 20】 A process B17 as represented by the above, comprising substitution of an unsaturated precursor 1,4 system by 1,4-addition using a Grignard reagent, such as 3-(trifluoromethyl)phenylmagnesium bromide; aa) The following scheme 【Chemistry 21】 A process B18 as represented by the above, comprising substitution of a 1,4 system by 1,4-addition using a Grignard reagent, such as 3-(trifluoromethyl)phenylmagnesium bromide; bb) scheme 【Chemistry 22】 A process B18a described in process B18 as represented by the process B18, comprising substitution of a 1,4 system by 1,4-addition using a Grignard reagent, such as 3-(trifluoromethyl)phenylmagnesium bromide; cc) The following scheme 【Chemistry 23】 Process B18b as described in Process B18, wherein the process includes substitution of a 1,4 system by 1,4-addition using a Grignard reagent, 3-(trifluoromethyl)phenylmagnesium bromide, etc.; dd) The following scheme 【Chemistry 24】 A process B18c as represented by the above, comprising a 1,4-substitution such as 1,4-addition using an organolithium reagent such as 3-(trifluoromethyl)phenyllithium; ee) The following scheme 【Chemistry 25】 A process B18d as represented by the above, which includes 1,4-addition or other substitution of 1,4 systems using an organozinc reagent such as 3-(trifluoromethylphenylzinc(II) bromide; ff) The following scheme 【Chemistry 26】 Process B19, represented by the above, is a process that includes substitution of a 1,4 system by reduction of the 1-methyl-2H-pyrrole-5-one double bond, such as by the use of a hydride source; gg) The following scheme 【Chemistry 27】 Process B19a, which is represented by process B19, and includes substitution of the 1,4 system by reduction of the double bond in the 1-methyl-2H-pyrrole-5-one group by the use of a hydride source, etc.; hh) The following scheme 【Chemistry 28】 A process B19b, such as the one represented by the formula, which includes, for example, substitution of a 1,4 system by reduction of a double bond in a 1-methyl-2H-pyrrole-5-one group using a hydride source; ii) The following scheme 【Chemistry 29】 A process B19c as represented by the above, which includes substitution of a 1,4 system by reduction of the double bond in the 1-methyl-2H-pyrrole-5-one group by the use of a hydride source, etc.; jj) The following scheme 【Transformation 30】 Process B20 as represented by the above, which includes substitution of a 1,4 system by reduction of the double bond in the 1-methyl-2H-pyrrole-5-one group by the use of a hydride source, etc.; kk) The following scheme 【Chemistry 31】 Process B21a for obtaining a saturated target from an unsaturated precursor, as represented by The process includes substitution of a 1,4 system by 1,4-addition using a Grignard reagent or a hydride source, wherein the saturated target is a compound as defined in claim 1 of application PCT / US2014 / 068073, published as international publication brochure 2015 / 084796, and Q １ Q ２ , R １ , R ２ , R ３ , R ４ , R ６ , Y １ and Y ２ The terms, etc., have the meanings defined in claim 1 of application PCT / US2014 / 068073, which is published as International Publication Brochure No. 2015 / 084796, and the substituents of the structure of this process are as defined for compound A35a; ll) The following scheme 【Chemistry 32】 Process B21b for obtaining a saturated target from an unsaturated precursor, as represented by The process involves 1,4-substitution such as 1,4-addition using a Grignard reagent or a hydride source, and the saturated target is a compound defined in claim 1 of the specification of application PCT / US2014 / 068073, published as WO 2015 / 084796 pamphlet, Q １ , Q ２ , R １ , R ２ , R ３ , R ４ , R ６ , Y １ and Y ２ etc. have the meanings defined in claim 1 of the specification of application PCT / US2014 / 068073, published as WO 2015 / 084796 pamphlet, and the substituents of the structure of this process are as defined for compound A35a, process; mm) The following scheme 【Transformation 33】 Process B21c for obtaining a saturated target from an unsaturated precursor, as represented by The process involves 1,4-substitution, such as 1,4-addition using a Grignard reagent or a hydride source, and the saturated target is a compound defined in claim 1 of the specification of application PCT / US2014 / 068073, published as WO 2015 / 084796 pamphlet, Q １ , Q ２ , R １ , R ２ , R ３ , R ４ , R ６ , Y １ and Y ２ etc. are as described in application P published as WO 2015 / 084796 pamphlet A process having the meaning defined in claim 1 of CT / US2014 / 068073, wherein the substituents of the process structure are as defined for compound A35a; nn) The following scheme 【Transformation 34】 A process B22, as represented by, which includes substitution of the unsaturated precursor 1,4 system; oo) The following scheme 【Chemistry 35】 A process B23, as represented by the above, comprising the substitution of the unsaturated precursor 1,4 system; pp) The following scheme 【Transformation 36】 A process B24, as represented by the above, comprising the substitution of the unsaturated precursor 1,4 system; qq) The following scheme 【Chemistry 37】 Process B25, as represented by, a process including substitution of the unsaturated precursor 1,4 system; rr) The following scheme 【Transformation 38】 A process B26, as represented by the above, comprising the substitution of the unsaturated precursor 1,4 system; ss) The following scheme 【Chemistry 39】 A process B27a, as represented by the above, comprising the substitution of the unsaturated precursor 1,4 system; tt) The following scheme 【Chemistry 40】 A process B27b, as represented by the above, comprising the substitution of the unsaturated precursor 1,4 system; uu) The following scheme 【Chemistry 41】 A process B28a, as represented by, which includes substitution of the 1,4 system by 1,4-addition, etc.; vv) The following scheme 【Chemistry 42】 A process B28b, as represented by the above, which includes substitution of a 1,4 system by 1,4-addition using an organolithium reagent such as 1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yllithium; lol) The following scheme 【Chemistry 43】 A process B29a, as represented by the above, which includes substitution of the 1,4 system by 1,4-addition, etc.; xx) The following scheme 【Chemistry 44】 Process B29b, as represented by, which includes substitution of a 1,4 system by 1,4-addition or the like using an organolithium reagent such as (6-(trifluoromethyl)pyridine-3-yl)lithium; yy) The following scheme 【Chemistry 45】 A process B30a, such as that represented by, which includes substitution of the 1,4 system by 1,4-addition, etc.; zz) The following scheme 【Chemistry 46】 A process B30b, as represented by, which includes 1,4-addition and other substitutions of the 1,4 system using an organolithium reagent such as 1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yllithium; aaa) Process B31 according to any one of processes B1 to B30b, which yields an excess amount of one or more possible isomers; bbb) Process B32 according to any one of processes B1 to B30b, which yields an excess amount of anti isomer; Process B33 according to any one of processes B1 to B30b, which yields an excess amount of the syn isomer (ccc); ddd) Process B34 according to any one of processes B1 to B33, wherein one or more possible chiral isomers are obtained in excess of the others; Process B35 according to any one of processes B1 to B34, yielding an excess of the chiral anti isomer; Process B36 according to any one of processes B1 to B34, which yields a chiral anti-isomer with an excess of S,S configuration; Process B37 as described in any one of Processes B1 to B36, wherein a reagent for substitution of the 1,4 system is prepared using magnesium, lithium, zinc, iPrMgCl, iPrMgBr, iPrMgI, hexyllithium, butyllithium, tert-butyllithium, 4-methylpentyllithium, isobutyllithium, or a combination thereof, before use in a substitution reaction; hhh) Process B38 as described in any one of processes B1 to B36, wherein magnesium halogen exchange or lithium halogen exchange is used in the preparation of reagents for the substitution of the 1,4 systems in situ and / or before use; iii) Process B39 as described in any one of processes B1 to B38, carried out in the presence of a metal; jjj) Process B40 according to Process B39, wherein the metal is selected from Cu; Ni; Ti; Co; and Fe; kkk) Process B41 according to Process B39, wherein the metal is selected from Cu; Ni; and Ti; lll) Process B42 according to Process B39, wherein the metal is Cu; mmm) Process B43 according to Process B39, wherein the metal is Ni; nnn) Process B44 according to any one of processes B39 to B43, wherein the metal is present in a catalytic amount; ooo) optionally, process B45 according to any one of processes B1 to B44, carried out in the presence of a chiral compound bonded to or part of a solid material or substrate; ppp) Process B46 as described in Process B45, wherein the chiral compound is selected from the group comprising naturally occurring, synthetic, modified (e.g., substituted, etc.) amino acids such as N,N-dimethyl-L-prolinium and L-proline; peptides exemplified by (S)-N-((S)-1-butylamino-1-oxo-3-phenylpropan-2-yl-2-(E)-2-diphenylphosphanalebenzylideneamino-3-methylbutanamide; phosphate ligands such as R-BINAP; proteins; enzymes; and sugars; qqq) Process B47 according to any one of Processes B45 to B46, wherein the chiral compound is selected from (S)-N-(S)-1-(butylamino-1-oxo-3-phenylpropane-2-yl-2-(E)-2-diphenylphosphanalebenzylideneamino-3-methylbutanamide); rrr) Process B48 according to any one of processes B45 to B47, wherein the chiral compound is present in a catalytic amount; sss) Lewis base, for example, NH ４ ＋ Cl － (Ammonium chloride); NH ４ ＋ OH － (Ammonium hydroxide); NH ３ ;CN － Ions (e.g., from KCN or NaCN); pyridine; DMA; DMSO; DMF; TEMADA; OH － Ions; pH ３ ; and H ２ PO ３ － Process B49, which is present in any one of processes B45 to B48 in post-treatment of ions, etc.; ttt) The Lewis base in post-processing is NH ４ ＋ Cl － (Ammonium chloride); NH ４ ＋ OH － (Ammonium hydroxide); NH ３ ; and CN from, for example, KCN or NaCN － Process B50 as described in Process B49, selected from ions, and uuu) For example, process B51 described in any one of processes B1 to B50, carried out in the presence of a strong base such as MeMgCl; MeMgBr; iPrMgCl; iPrMgBr; BuLi; tert-BuLi; lithium hexyl; NaH; KH.

3. Processes B16; B16a; B16p; B16c; B16d; B17; B18; B18a; B18p; B18c; B18d; B19; B19a; B19p; and Process B19 A process selected from one of the following options (c).

4. A process mediated by exposure of the starting compound to sunlight, represented by the following scheme. 【Chemistry 47】

5. A process for generating a conserved marker compound of formula D represented by the following scheme, 【Chemistry 48】 A process in which the conversion rate and degree of conversion of the generated formula D to a storage marker compound, as well as its amount and its content in a mixture with the composition of the generated compound, are mediated by the properties of the composition and its storage history under various defined environmental conditions, particularly exposure to sunlight.

6. Unsaturated precursor compound A1 of formula 2 and, for example, its salt, 【Chemistry 49】 (In the formula, R α This includes halogens; carbon-containing groups exemplified by substituted or unsubstituted alkyl, aryl, heterocyclic, and naphthyl groups; and C(O)OC ６ H ５ , -C(O)OC ６ H ４ Esters including aliphatic and aromatic esters as exemplified by F; -C(O)NHC ６ H ５ Amides including aliphatic and aromatic amides as exemplified by: -C(O)NHNHC ６ H ５ Hydrazine amides, thioesters, thionoesters, and for example, C(O)NHOC, including aliphatic and aromatic hydrazine amides as exemplified by the above. ６ F ５ ;-C(S)SC ６ H ５ These are similar compounds, however, R α Since it is not bonded to the ring via O or N, R α It cannot be -OMe, R β This refers to carbon-containing elements such as substituted or unsubstituted alkyl, aryl, naphthyl, heterocyclic rings, etc., bonded to the ring via hydrogen or a C atom or, where applicable, a Si atom. It is the basis, however, R β This is not an amine bonded to the ring via N. R β This is not an ether bonded to the ring via O, R β This is not a thioether bonded to the ring via S, A α This is a C, N, O, or S atom that has or does not have substitution by -N(Me)- or -O-, etc., and if present, A α The substituents also include Q in the following structures, etc. α A β It may also be bound to other parts of molecules such as [Transformation 50] Each A β These are, individually and independently, -CH ２ C, N, O, or S atoms that have or do not have substitutions such as - or -O-, and if present, each A β The substituents are A α A β , R β It may also be bonded to another part of the molecule, however A β At least one of them is CH ２ A saturated atom as exemplified by, nα is 1, 2, or 3. Each Q α These are individually and independently O, S, or NR ε And, R ε is -N(Me) ２ A C, N, O, or S atom having or not having substitution by the like, R ε The substituents above, if present, may be hydrogen or carbon and / or nitrogen-containing groups, for example, substituted or unsubstituted alkyl, aryl, naphthyl, heterocyclic, etc., bonded to the ring via a C atom, or, if applicable, a Si atom, if present, R ε The substituents are Q atoms in the ring via the C atom or, if applicable, the Si atom, as shown in the following structure. α A β It may also be bound to other parts of molecules such as 【Chemistry 51】 Preferably, the ring portion of the P-labeled unsaturated precursor in the following structure is not aromatic, so not all atoms can be conjugated. 【Chemistry 52】 Furthermore, the double bond in that ring portion is not part of the outer aromatic addition ring.

7. Unsaturated precursor compound A2 of formula 2 and, for example, a salt thereof, 【Chemistry 53】 In the formula, the unsaturated precursor does not contain a covalent nitrogen-halogen bond. R α Halogen (Ha.), C １ ~C １０ Alkyl, C １ ~C １０ Haloalkyl, R μ or -C(Q) α ) Q β R μ And, Optionally, R α Also, another part of the molecule, for example, Q in the ring. α A β They may be connected to each other, Q β O, S, NR ε , NR π -NR π , NR π -O, NR π -S, S-NR π , or O-NR π And, R β H, R ε , or Si(R ε ) ３ And, A α is a C, N, O, or S atom having 0 to 2 substituents, where the substituents are H and / or R, if present. θ You may choose from the following, and optionally, A α A is selected from -N(Me)-, -C(Et)H-, and -O-, and is optionally present if present. α The substituents are located on other parts of the molecule, such as Q, as shown in the following structure. α A β They are linked as rings, 【Chemistry 54】 Each A β Each is an independent C, N, O, or S atom having 0 to 2 substituents, and optionally A β is one of -N(Me)-, -C(Et)H-, -O-, etc., and each A β The substituents above are H and / or R θ Selected from, provided that A on the ring β At least one of the atoms is CH ２ The condition is that the atoms are saturated atoms, Arbitrarily, each A β Q α A α Another part of the molecule or another A β They may be bonded to each other to form a ring, nα is between 1 and 3. Q α O, S, NR ε And, arbitrarily, Q α A within the ring β It may also be bonded to another part of the molecule, Each R θ These are, individually and independently, halogen (Ha.), hydroxyl (OH), cyano (CN), nitro, amino, and C. １ ~C ８ Alkyl, C １ ~C ８ Cyanoalkyl, C １ ~C ８ Cyanoalkoxy, C １ ~C ８ Haloalkyl, C １ ~C ８ Hydroxyalkyl, C １ ~C ８ Nitroalkyl, C ２ ~C ８ Alkenil, C ２ ~C ８ Haloalkenil, C ２ ~C ８ Nitroalkenyl, C ２ ~C ８ Alkinyl, C ２ ~C ８ Haloalkynyl, C ２ ~C ８ Alkoxyalkyl, C ３ ~C ８ Alkoxyalkoxyalkyl, C ２ ~C ８ Haloalkoxyalkyl, C ２ ~C ８ Haloalkoxyhaloalkoxy, C ３ ~C ６ Cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C ４ ~C １０ Cycloalkylalkyl, C ４ ~C １０ Halocycloalkylalkyl, C ５ ~C １２ Alkylcycloalkylalkyl, C ５ ~C １２ Cycloalkylalkenyl, C ５ ~C １２ Cycloalkylalkynyl, C ３ ~C ８ Cycloalkyl, C ３ ~C ８ Halocycloalkyl, C ４ ~C １０ Alkylcycloalkyl, C ６ ~C １２ Cycloalkylcycloalkyl, C ３ ~C ８ Cycloalkenyl, C ３ ~C ８ Halocycloalkenyl, C ２ ~C ８ Haloalkoxyalkoxy, C ２ ~C ８ Alkoxyalkoxy, C ４ ~C １０ Cycloalkoxyalkyl, C ３ ~C １０ Alkoxyalkoxyalkyl, C ２ ~C ８ Alkylthioalkyl, C ２ ~C ８ Alkylsulfinylalkyl, C ２ ~C ８ Alkylsulfonylalkyl, C ２ ~C ８ Alkylamino, C ２ ~C ８ Dialkylamino, C ２ ~C ８ Halodialkylamino, C ２ ~C ８ Alkylaminoalkyl, C ２ ~C ８ Haloalkylaminoalkyl, C ４ ~C １０ Cycloalkylaminoalkyl, C ３ ~C １０ Dialkylaminoalkyl, -CHO, C ２ ~C ８ Alkylcarbonyl, C ２ ~C ８ Haloalkylcarbonyl, C ４ ~C １０ Cycloalkylcarbonyl, -C(isO)OH, C ２ ~C ８ Alkoxycarbonyl, C ２ ~C ８ Haloalkoxycarbonyl, C ４ ~C １０ Cycloalkoxycarbonyl, C ５ ~C １２ Cycloalkylalkoxycarbonyl, -C(isO)NH ２ , C ２ ~C ８ Alkylaminocarbonyl, C ４ ~C １０ Cycloalkylaminocarbonyl, C ３ ~C １０ Dialkylaminocarbonyl, C １ ~C ８ Alkoxy, C １ ~C ８ Haloalkoxy, C ２ ~C ８ Alkoxyalkoxy, C ２ ~C ８ Alkenyloxy, C ２ ~C ８ Haloalkenyloxy, C ３ ~C ８ Alkynyloxy, C ３ ~C ８ Haloalkynyloxy, C ３ ~C ８ Cycloalkoxy, C ３ ~C ８ Halocycloalkoxy, C ４ ~C １０ Cycloalkylalkoxy, C ３ ~C １０ Alkylcarbonylalkoxy, C ２ ~C ８ Alkylcarbonyloxy, C ２ ~C ８ Haloalkylcarbonyloxy, C ４ ~C １０ Cycloalkylcarbonyloxy, C １ ~C ８ Alkyl sulfonyl oxy, C １ ~C ８ Haloalkylsulfonyloxy, C １ ~C ８ Alkylthio, C １ ~C ８ Haloalkylthio, C ３ ~C ８ Cycloalkylthio, C １ ~C ８ Alkyl sulfinyl, C １ ~C ８ Haloalkylsulfinyl, C １ ~C ８ Alkyl sulfonyl, C １ ~C ８ Haloalkylsulfonyl, C ３ ~C ８ Cycloalkylsulfonyl, formylamino, C ２ ~C ８ Alkylcarbonylamino, C ２ ~C ８ Haloalkylcarbonylamino, C ３ ~C ８ Cycloalkylamino, C ２ ~C ８ Alkoxycarbonylamino, C １ ~C ６ Alkyl sulfonyl amino, C １ ~C ６ Haloalkylsulfonylamino, -SF ５ ,-SCN,SO ２ NH ２ , C ３ ~C １２ Trialkylsilyl, C ４ ~C １２ Trialkylsilylalkyl, C ４ ~C １２ Trialkylsilylalkoxy, R σ , R η S(=O)=N-,R η S (=O) ２ N, R η -C(=O)-, R η (R η N=) ｑ S (=O) ｐ - Cyano, Formil, C ３ ~C ８ Alkylcarbonylalkyl, -C(C １ ~C ４ Alkyl) = N-O(C １ ~C ４ Alkyl), -C(O)NH ２ , C ２ ~C ６ Cyanoalkyl, C ３ ~C ６ Cycloalkyl, C ４ ~C ８ Cycloalkenyl, arylcarbonyl, arylalkenylalkyl, arylcarbonylalkyl or -CPh=N-O(C １ ~C ４ Alkyl) and each of these is R η Optionally substituted on a ring member having up to five substituents independently selected from R θ If it is bonded to another part of the molecule, the bond is Up to 4 carbon atoms, Up to one oxygen atom, Up to one S atom and A saturated, partially unsaturated, or fully unsaturated chain containing 2 to 4 atoms selected from up to 2 N atoms, Up to two carbon members of the chain are independently selected from C(=O) and C(=S), and the sulfur member of the chain is S(-O) ｕ (-NR ζ ) ｖ Selected from, the chain is substituted on carbon atoms and / or nitrogen atoms R η It is optionally substituted with up to five substituents independently selected from the original compound. R λ H or R μ And, R λ Q α A β It may also be bonded to another part of the molecule, R μ is a phenyl ring or naphthalenyl ring system, where each ring or ring system is unsubstituted or R ζ Phenyl or naphthalenyl ring systems substituted with up to five substituents independently selected from; 4- to 7-membered heterocyclic rings; and 8- to 10-membered bicyclic ring systems, wherein each ring or ring system is composed of carbon atoms and Up to two oxygen atoms, Up to two S atoms, and It contains ring members selected from 1 to 4 heteroatoms independently selected from up to 5 N atoms, Up to three C ring members are independently selected from C(=O) and C(=S), and the sulfur ring member is independently selected from S(=O). ｕ (=NR ζ ) ｖ Selected from, each ring or ring system is R of carbon atom ring members ζ Independently selected from, the nitrogen atom ring member R η It is substituted with up to five substituents selected from or is unsubstituted. R π H or R θ And, R ε Each of these is -N(Me) ２ etc. R π A C, N, O, or S atom having 0 to 2 substituents selected from, where the substituents are optionally, for example, Q α A β They are additionally bonded within the ring to other parts of molecules such as Each R ζ These are, individually and independently, Ha, OH, CN, nitro, amino, and C. １ ~C ８ Alkyl, C １ ~C ８ Cyanoalkyl, C １ ~C ８ Cyanoalkoxy, C １ ~C ８ Haloalkyl, C １ ~C ８ Hydroxyalkyl, C １ ~C ８ Nitroalkyl, C ２ ~C ８ Alkenil, C ２ ~C ８ Haloalkenil, C ２ ~C ８ Nitroalkenyl, C ２ ~C ８ Alkinyl, C ２ ~C ８ Haloalkynyl, C ２ ~C ８ Alkoxyalkyl, C ３ ~C ８ Alkoxyalkoxyalkyl, C ２ ~C ８ Haloalkoxyalkyl, C ２ ~C ８ Haloalkoxyhaloalkoxy, C ３ ~C ６ Cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl, 2-methylcyclopropyl, C ４ ~C １０ Cycloalkylalkyl, C ４ ~C １０ Halocycloalkylalkyl, C ５ ~C １２ Alkylcycloalkylalkyl, C ５ ~C １２ Cycloalkylalkenyl, C ５ ~C １２ Cycloalkylalkynyl, C ３ ~C ８ Cycloalkyl, C ３ ~C ８ Halocycloalkyl, C ４ ~C １０ Alkylcycloalkyl, C ６ ~C １２ Cycloalkylcycloalkyl, C ３ ~C ８ Cycloalkenyl, C ３ ~C ８ Halocycloalkenyl, C ２ ~C ８ Haloalkoxyalkoxy, C ２ ~C ８ Alkoxyalkoxy, C ４ ~C １０ Cycloalkoxyalkyl, C ３ ~C １０ Alkoxyalkyl, C ２ ~C ８ Alkylthioalkyl, C ２ ~C ８ Alkylsulfinylalkyl, C ２ ~C ８ Alkylsulfonylalkyl, C ２ ~C ８ Alkylamino, C ２ ~C ８ Dialkylamino, C ２ ~C ８ Halodialkylamino, C ２ ~C ８ Alkylaminoalkyl, C ２ ~C ８ Haloalkylaminoalkyl, C ４ ~C １０ Cycloalkylaminoalkyl, C ３ ~C １０ Dialkylaminoalkyl, -CHO, C ２ ~C ８ Alkylcarbonyl, C ２ ~C ８ Haloalkylcarbonyl, C ４ ~C １０ Cycloalkylcarbonyl, -C(isO)OH, C ２ ~C ８ Alkoxycarbonyl, C ２ ~C ８ Haloalkoxycarbonyl, C ４ ~C １０ Cycloalkoxycarbonyl, C ５ ~C １２ Cycloalkylalkoxycarbonyl, -C(=O)NH ２ , C ２ ~C ８ Alkylaminocarbonyl, C ４ ~C １０ Cycloalkylaminocarbonyl, C ３ ~C １０ Dialkylaminocarbonyl, C １ ~C ８ Alkoxy, C １ ~C ８ Haloalkoxy, C ２ ~C ８ Alkoxyalkoxy, C ２ ~C ８ Alkenyloxy, C ２ ~C ８ Haloalkenyloxy, C ３ ~C ８ Alkynyloxy, C ３ ~C ８ Haloalkynyloxy, C ３ ~C ８ Cycloalkoxy, C ３ ~C ８ Halocycloalkoxy, C ４ ~C １０ Cycloalkylalkoxy, C ３ ~C １０ Alkylcarbonylalkoxy, C ２ ~C ８ Alkylcarbonyloxy, C ２ ~C ８ Haloalkylcarbonyloxy, C ４ ~C １０ Cycloalkylcarbonyloxy, C １ ~C ８ Alkyl sulfonyl oxy, C １ ~C ８ Haloalkylsulfonyloxy, C １ ~C ８ Alkylthio, C １ ~C ８ Haloalkylthio, C ３ ~C ８ Cycloalkylthio, C １ ~C ８ Alkyl sulfinyl, C １ ~C ８ Haloalkylsulfinyl, C １ ~C ８ Alkyl sulfonyl, C １ ~C ８ Haloalkylsulfonyl, C ３ ~C ８ Cycloalkylsulfonyl, formylamino, C ２ ~C ８ Alkylcarbonylamino, C ２ ~C ８ Haloalkylcarbonylamino, C ３ ~C ８ Cycloalkylamino, C ２ ~C ８ Alkoxycarbonylamino, C １ ~C ６ Alkyl sulfonyl amino, C １ ~C ６ Haloalkylsulfonylamino, -SF ５ ,-SCN,SO ２ NH ２ , C ３ ~C １２ Trialkylsilyl, C ４ ~C １２ Trialkylsilylalkyl, C ４ ~C １２ Trialkylsilylalkoxy, R η , R η S(=O)=N-,R η S (=O) ２ NR η -C (=O)- or R η (R η N=) ｑ S (=O) ｐ - and the free bond protruding to the right is R μ The connection points to etc are indicated, and arbitrarily, R ζ This refers to the other parts of the ring-forming molecule, for example, Q α A β It may be combined with the following: Each R η These are, individually and independently, CN, C １ ~C ３ Alkyl, C １ ~C ８ Hydroxyalkyl, C ２ ~C ３ Alkenil, C ２ ~C ３ Alkinyl, C ３ ~C ６ Cycloalkyl, C ２ ~C ３ Alkoxyalkyl, C １ ~C ３ Alkoxy, C ２ ~C ３ Alkylcarbonyl, C ２ ~C ３ Alkoxycarbonyl, C ２ ~C ３ Alkylaminoalkyl or C ３ ~C ４ It is a dialkylaminoalkyl, and optionally R η This refers to the other parts of the ring-forming molecule, for example, Q α A β It may be combined with the following: Each R σ These are, individually and independently, phenyl, phenylmethyl (benzyl), pyridinylmethyl, Phenylcarbonyl (i.e., benzoyl), phenoxy, phenylethynyl, phenylsulfonyl, or a 5-membered or 6-membered heterocyclic ring, each being R λ The ring member having up to five substituents independently selected from is substituted or unsubstituted, q is between 0 and 4. p is between 0 and 4. u is between 0 and 4. v is 0 to 4, and is an unsaturated precursor compound A2 of formula 2 and, for example, a salt thereof.

8. Formula 2, selected from the group defined, illustrated, or described in any one of the unsaturated precursor compounds described in claim 6(A1) or claim 7(A2). 【Transformation 55】 An unsaturated precursor compound, or any compound selected from the following group: A2; A2a; A2b; A2c; A2d; A3; A4; A5; A6; A7; A8; A9; A10; A11; A12; A13; A14; A15; A16; A16a; A17; A17a; A18; A19; A20; A21; A22; A23; A24; A25; A26; A27; A28; A29; A30; A31; A32; A33; A34; and A35a: a. The unsaturated precursor compound A1 of formula 2 as described in claim 6, and, for example, a salt thereof; b. The unsaturated precursor compound A2 of formula 2 as described in claim 7, and, for example, a salt thereof; c. Compound A2 is an unsaturated precursor compound A2a and, for example, a salt thereof (wherein the formula, nα is 1, R α , R β Q α Q β A β A α , and R μ (This has the same meaning as defined in compound A2); d. Compound A2 is an unsaturated precursor compound A2b and, for example, a salt thereof (wherein the formula, nα is 2, R α , R β Q α Q β A β A α , and R μ (This has the same meaning as defined in compound A2); e. Compound A2 is an unsaturated precursor compound A2c and, for example, a salt thereof (wherein the formula, R β H is, R α Q α Q β A β A α , R μ (and nα have the same meaning as defined in compound A2); f. Compound A2 is an unsaturated precursor compound A2d and, for example, a salt thereof (wherein the formula, R α , R β Q α Q β A β A α , R μ And nα have the same meaning as defined in compound A2, however, R β (This is not H). g. Unsaturated compound A2, A2a, A2b, A2c, or A2d Carrier compound A3 and, for example, its salt (in the formula, R α is -C(Q α ) Q β R μ , or the following structure, 【Transformation 56】 And, R β Q α Q β A β A α , R μ (and nα have the same meaning as defined in compound A2); h. Unsaturated precursor compound A4 which is any one of compound A2; A2a; A2b; A2c; or A2d, and for example, a salt thereof (wherein, R α is -C(Q α ) Q β R μ And, A α As shown in the following ring structure, -N(R π ) - and 【Chemistry 57】 R β Q α Q β A β , R π , R μ (and nα have the same meaning as defined in compound A2); i. Unsaturated precursor compound A5 which is any one of compound A2; A2c; or A2d, and, for example, a salt thereof (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) and nα is 1, as shown in the following ring structure. 【Chemistry 58】 R β Q α Q β A β , R π and R μ (This has the same meaning as defined in compound A2); j. Unsaturated precursor compound A6 which is one of compounds A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 1, A β CH is as shown in the following ring structure ２ And, 【Chemistry 59】 R β Q α Q β , R π and R μ (This has the same meaning as defined in compound A2); k. Unsaturated precursor compound A7 which is one of compounds A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 2, A β CH is as shown in the following ring structure ２ And, 【Transformation 60】 R β Q α Q β , R π and R μ (This has the same meaning as defined in compound A2); l. Unsaturated precursor compound A8 which is one of compounds A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(O)Q β R μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O as shown in the following ring structure, 【Chemistry 61】 R β Q β , R π and R μ (This has the same meaning as defined in compound A2); m. Unsaturated precursor compound A9 which is one of compounds A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β It is NH as shown in the following ring structure, 【Transformation 62】 R β , R π and R μ (This has the same meaning as defined in compound A2); n. Unsaturated precursor compound A10 which is one of compounds A2; A2c; and A2d, and, for example, a salt thereof (wherein, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R as in the following ring structure ζ A phenyl ring substituted with up to five substituents independently selected from, 【Transformation 63】 R β , R π and R ζ (This has the same meaning as defined in compound A2); o. Compound A2 is an unsaturated precursor compound A11 and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β It is either unsubstituted or R as in the following ring structure ζ R is a phenyl ring substituted with up to five substituents independently selected from λ And, 【Chemistry 64】 R π and R ζ (This has the same meaning as defined in compound A2); p. Compound A2 is an unsaturated precursor compound A12 and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β It is either unsubstituted or R as in the following ring structure ζ R is a phenyl ring substituted with up to five substituents independently selected from λ And, 【Transformation 65】 R ζ (This has the same meaning as defined in compound A2); q. Compound A2 is an unsaturated precursor compound A13 and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β It is either unsubstituted or R as in the following ring structure ζ R is a phenyl ring substituted with up to five substituents independently selected from λ And, 【Chemical 66】 R ζ (This has the same meaning as defined in compound A2); r. Compound A2 is an unsaturated precursor compound A14 and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 2, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from, R β It is either unsubstituted or R as in the following ring structure ζ R is a phenyl ring substituted with up to five substituents independently selected from each of the following. λ And, 【Transformation 67】 R ζ (This has the same meaning as defined in compound A2); s. Compound A2 is an unsaturated precursor compound A15, and for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 2, a. A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from, R β It is either unsubstituted or R as in the following ring structure ζ R is a phenyl ring substituted with up to five substituents independently selected from each of the following. λ And, 【Transformation 68】 R ζ (This has the same meaning as defined in compound A2); t. Unsaturated precursor compound A16 having the following structure, 【Transformation 69】 u. Unsaturated precursor compound A16a having the following structure, 【Transformation 70】 v. Unsaturated precursor compound A17 having the following structure, 【Chemistry 71】 w. A pesticide synthesis intermediate compound A17a having the following structure, 【Chemistry 72】 x. Unsaturated precursor compound A18 having the following structure, 【Transformation 73】 y. Unsaturated precursor compound A19 having the following structure, 【Chemistry 74】 z. Unsaturated precursor compound A20 having the following structure, 【Chemistry 75】 aa. Unsaturated precursor compound A21 having the following structure, 【Transformation 76】 bb. Unsaturated precursor compound A22 having the following structure, 【Chemical Formula 77】 cc. Unsaturated precursor compound A23 having the following structure, 【Transformation 78】 dd. Unsaturated precursor compound A24 having the following structure, 【Transformation 79】 ee. Unsaturated precursor compound A25 having the following structure, 【Chemistry 80】 ff. Unsaturated precursor compound A26 having the following structure, 【Chemistry 81】 gg. Unsaturated precursor compound A27 having the following structure, 【Chemistry 82】 hh. Unsaturated precursor compound A28 having the following structure, 【Chemistry 83】 ii. Unsaturated precursor compound A29 having the following structure, 【Chemical 84】 jj. Unsaturated precursor compound A30 having the following structure, 【Chemical 85】 kk. Compound A2 is an unsaturated precursor compound A31 and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R as in the following ring structure ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is as shown in the following ring structure, i. 【Chemical 86】 R π and R ζ (This has the same meaning as defined in compound A2); ll. Compound A2 is an unsaturated precursor compound A32 and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R as in the following ring structure ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is as shown in the following ring structure, 【Chemistry 87】 R ζ (This has the same meaning as defined in compound A2); mm. Compound A2 is an unsaturated precursor compound A33 and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 2, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R as in the following ring structure ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is as shown in the following ring structure, 【Chemical 88】 R ζ (This has the same meaning as defined in compound A2); nn. Compound A2 is an unsaturated precursor compound A34 and, for example, a salt thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 2, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R as in the following ring structure ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is as shown in the following ring structure, 【Chemistry 89】 R ζ (This has the same meaning as defined in compound A2), and oo. Unsaturated precursor compound A35a selected from the following structures, [Chemical 90] (In the formula, Q １ Q ２ , R １ , R ２ , R ３ , R ４ , R ６ Y1 and Y2, etc., have the meanings defined in claim 1 of the international application PCT / US2014 / 068073, which was published as international publication brochure 2015 / 084796.

9. A compound defined, illustrated or described in any one selected from A1; A2; A2a; A2b; A2c; A2d; A3; A4; A5; A6; A7; A8; A9; A10; A11; A12; A13; A14; A15; A16; A16a; A17; A17a; A18; A19; A20; A21; A22; A23; A24; A25; A26; A27; A28; A29; A30; A31; A32; A33; A34; and A35a of claim 8, agricultural An unsaturated precursor for use as a pharmaceutical, preferably as an intermediate in the herbicide synthesis process and / or as a marker compound.

10. A compound defined, illustrated, or described in any one of the compounds selected from A16; A16a; A17; A17a; A18 and A19 of claim 8.

11. A compound defined, illustrated, or described in compound A16 of claim 8.

12. A compound defined, illustrated, or described in compound A17 of claim 8.

13. A combination defined, illustrated, or described as one of the following combinations selected from A41a; A42a; A43a; B1a; B15b; B15d; C2b; C35b; C36b; C37c; C38a; C41; C42a; C43a; E2; M1; M2; M3; M4. a. Each has the following structure 【Chemistry 91】 A combination of a saturated target, N-oxide and its salt, A41a, of the following formula, as defined in claim 1 of PCT / US2018 / 035017, published as International Publication No. 2018 / 222647, combined with at least one unsaturated precursor defined by any one of the following: 【Chemistry 92】 (In the formula, Q １ Q ２ , R １ , R ７ , R ９ (J, L, Y, and Y2, etc., have the meanings defined in claim 1 of application PCT / US2018 / 035017, which was published as international publication brochure 2018 / 222647); b. Each has the following structure 【Chemistry 93】 Combined with at least one saturated precursor defined by any one of the following, A42a is a combination of a saturated target, its N-oxide salt, and a stereoisomer, which is a compound defined in claim 1 of PCT / US2018 / 035015, published as International Publication No. 2018222646. 【Chemical 94】 (In the formula, Q1, Q2, R1, R7, R8, R9, J, Y, and W, etc., have the meanings defined in claim 1 of application PCT / US2018 / 035015, which was published as international publication brochure 2018 / 222646); c. Each has a structure 【Chemical 95】 A saturated target and salt thereof, in combination with at least one unsaturated precursor defined by any one of the following, wherein the saturated target is a compound defined in claim 1 of PCT / EP2018 / 057628, published as International Publication Brochure No. 2018 / 184890, the saturated target and salt combination A43a 【Chemistry 96】 (In the formula, Q, W ２ , R １ , R ２ (Y and Z, etc., have the meanings defined in claim 1 of application PCT / EP2018 / 057628, which was published as international publication brochure 2018 / 184890); d. The amount of intermediate unsaturated precursor compound as an impurity, selected from compounds A1 to A52 of process B1 and formula 2, and produced therefrom, 【Chemistry 97】 Combination of saturated targets B1a of Equation 1 defined in process B1 【Chem.98】 e. Combination B15b of saturated targets defined in process B1, which is produced as an impurity using any one of processes B1 to B14, in combination with an intermediate unsaturated precursor compound; f. Combinations B15d of saturated targets defined in process B1, which are produced as impurities by any one of processes B1 to B14, and are paired with an intermediate unsaturated precursor compound; g. A combination C2b of the saturated target compound of formula 1, which is produced as an impurity and is combined with the intermediate compound of formula 3, 【Chem.99】 The intermediate is a compound defined by any one of compounds C1a; C1b; C1c; and C2, R γ However, any combination that has the same meaning as defined by any one of processes B1, B1a, B1b; B2, and B2a; h. At least one compound defined by one of the following formulas, 【Chemistry 100】 (where Q １ , Q ２ , R １ , R ２ , R ３ , R ４ , R ６ , Y １ and Y ２ etc. have the meanings defined in claim 1 of the specification of application PCT / US2014 / 068073, published as International Publication No. 2015 / 084796 pamphlet, X α =SPh、SePh、SG α 、SeG α G α = alkyl, haloalkyl, phenyl (phenyl substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups, respectively), and the following structures 【Chemistry 101】 C35b is a combination of saturated target compounds having the following properties: i. At least one compound defined by any one of the following formulas, 【Chemical Engineering 102】 (In the formula, Q, R １ , R ６ Y and W, etc., have the meanings defined in claim 1 of application PCT / US2020 / 034232, which was published as international publication brochure 2020 / 242946. X α SPh, SePh, SG α SeG α And, G α The following structure is formed when combined with alkyl, haloalkyl, or phenyl (phenyl is substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups, respectively). 【Chemistry 103】 C36b is a combination of saturated target compounds having the following properties: j. At least one compound defined by any one of the following formulas, 【Chemical 104】 (In the formula, Q １ Q ２ , R １ , R ２ , R ７ Y, A, and J, etc., have the meanings defined in claim 1 of application PCT / US2016 / 030450, which was published as international publication brochure 2016 / 182780. X α SPh, SePh, SG α SeG α And, G α The following structure is formed when combined with alkyl, haloalkyl, or phenyl (phenyl is substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups, respectively). 【Chemistry 105】 C37c is a combination of saturated target compounds having the following properties: k. At least one compound defined by any one of the following structures, 【Chemistry 106】 (In the formula, Q １ Q ２ , R Ｂ１ , and X etc. have the meanings defined in claim 1 of application PCT / EP2020 / 052780, which was published as international publication brochure 2020 / 161147. X α SPh, SePh, SG α SeG α And, G α Application PCT / EP2020 / 052780, published as International Publication Brochure 2020 / 161147, is a combination of alkyl, haloalkyl, and phenyl (phenyl substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups, respectively). The following formula as defined in claim 1(B) 【Chemistry 107】 The combination of saturated target compounds C38a; l. At least one compound, each defined by one of the following structures, 【Chemistry 108】 (In the formula, Q １ Q ２ , R １ , R ７ , R ９ , J, L, Y and Y ２ "etc." has the meaning defined in claim 1 of application PCT / US2018 / 035017, which was published as international publication brochure 2018 / 222647. X α SPh, SePh, SG α SeG α And, G α The following formula is defined in claim 1 of application PCT / US2018 / 035017, published as international publication brochure 2018 / 222647, and is combined with alkyl, haloalkyl, and phenyl (phenyl substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups, respectively): 【Chemistry 109】 Saturated target combination C41; m. A combination C42a of a saturated target, its N-oxide, and stereoisomer, wherein the A saturated target is at least one compound defined by one of the following structures: 【Chemical 110】 (In the formula, Q １ Q ２ , R １ , R ７ , R ８ , R ９ J, Y, and W, etc., have the meanings defined in claim 1 of application PCT / US2018 / 035015, which was published as international publication brochure 2018 / 222646. X α SPh, SePh, SG α SeG α And, G α The following formula is formed when combined with alkyl, haloalkyl, or phenyl (phenyl is substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups, respectively): 【Chemistry 111】 A combination having the compound defined in claim 1 of application PCT / US2018 / 035015, published as international publication brochure 2018 / 222646; n. The following structure 【Chemistry 112】 (In the formula, Q, W ２ , R １ , R ２ Y and Z, etc., have the meanings defined in claim 1 of application PCT / EP2018 / 057628, which was published as international publication brochure 2018 / 184890. X α SPh, SePh, SG α SeG α And, G α A combination of a saturated target and its salt C43a is a compound defined in claim 1 of application PCT / EP2018 / 057628, published as international publication brochure C2018 / 184890, having the following formula, in combination with at least one compound defined by one of alkyl, haloalkyl, or phenyl (phenyl substituted with 0 to 5 groups selected from a halogen group; alkyl; and haloalkyl, respectively), 【Chemistry 113】 o. Equation 4, which is produced as an impurity. 【Chemistry 114】 (In the formula, R α , R β A α A β , nα and Q α This has the same meaning as defined in compound A2, and R δ and R γ Combinations E2 of saturated target compounds of formula 1, which are combined with intermediate compounds (which have the same meaning as defined in process B1) and, for example, salts thereof. 【Chemical 115】 p. The following formula: 【Chemistry 116】 (In the formula, each R ζ A combination of saturated targets M1 of formula 1 as defined in process B1, in combination with one amount of a marker, an impurity, or a degradable compound having compounds A1 to A52 (as defined in process B1). 【Chemistry 117】 q. The following formula: 【Chemistry 118】 A combination of saturated targets M2 of formula 1 defined in process B1, in combination with one of the following amounts: a marker, an impurity, or a degradable compound. 【Chemical 119】 r. The following formula: 【Chemical 120】 A marker having one of the following amounts: impurities, or degradable compounds, combined with a pro Combination of saturated targets M3 in Equation 1 as defined by Seth B1 【Chemistry 121】 s. The following formula: 【Chemistry 122】 (where each R θ and each R ζ is as defined in compound A2), a combination M4 of saturated targets of formula 1 defined in process B1, combined with the amount of any one of a marker, an impurity, and a degradable compound. 【Chemical 123】

14. Compound C1a; C1b; C1c; C2; C3a; C3b; C4a; C4b; C5a; C5b; C5c; C6a; C6b; C7a; C7b; C8a; C12; C12a; C12b; C13; C14; C15; C16; C16a; C16b; C16c; C16d; C16e; C16f; C16g; C16h; C17a; C17e; C17f; C17g; C17h; C17i; C18a; C18b; C19a; C19b; C20a; C20b; C21a; C21b; C22a; C24b; C25a; C25b; C26a; C26b; C27a; C27b; C28a; C28b; C29a; C29b; C30a; C30b; C31a; C31b; C32a; Compounds defined, illustrated, or described in any one of C34; C35a; C36a; C37a; C37b; C38; C39; C40; C42; and C43, or compounds selected from the following groups: (a) Compound C1a of formula 3 and, for example, its salts, etc. 【Chemistry 124】 (In the formula, X α SPh, SePh, SG α SeG α And, G α R is a phenyl compound substituted with 0 to 5 groups selected from alkyl, haloalkyl, and phenyl, respectively, from halogen groups; alkyl groups; and haloalkyl groups. α , R β A α A β , nα and Q α (This has the same meaning as defined in compound A2); (b) Compound C1b of formula 3 and, for example, its salts. 【Chemistry 125】 (In the formula, X α It is a halogen, R α , R β A α A β , nα and Q α (This has the same meaning as defined in compound A2); (c) Compound C1c of formula 3 and, for example, its salts. 【Chemistry 126】 (In the formula, X α is N(G α ) ２ , N ＋ (O － ) (G α ) ２ [That is, N(G α ) ２ It is the N-oxide of, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. R α , R β A α A β , nα and Q α (This has the same meaning as defined in compound A2); (d) Compound C2 of formula 3 and, for example, its salts. 【Chemistry 127】 (In the formula, the compound of formula 3 does not contain a covalent nitrogen-halogen bond.) X α Halogen, SPh, SePh, SG α SeG α And, G α R is a phenyl compound substituted with 0 to 5 groups selected from alkyl, haloalkyl, and phenyl, respectively, from halogen groups; alkyl groups; and haloalkyl groups. α , R β , A α A β , nα and Q α (This has the same meaning as defined in compound A2); (e) Compound C3a of compound C2 and, for example, salts thereof as process intermediates and / or markers (wherein R α is -C(Q α ) Q β R μ And, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogens, alkyls, and haloalkyls, respectively. 【Chemistry 128】 R β Q α Q β A β A α , R μ (and nα have the same meaning as defined in compound A2); (f) Compound C3b of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(Q α ) Q β R μ And, X α Halogen, N(G α ) ２， N ＋ (O － ) (G α ) ２ And, 【Chemistry 129】 R β Q α Q β A β A α , R μ (and nα have the same meaning as defined in compound A2); (g) Compound C4a of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogens, alkyls, and haloalkyls, respectively. 【Chemistry 130】 R β Q α Q β A β , R π , R μ (and nα have the same meaning as defined in compound A2); (h) Compound C4b of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and X α Halogen, N(G α ) ２， N ＋ (O － ) (G α ) ２ And, 【Chemistry 131】 R β Q α Q β A β , R π , R μ (and nα have the same meaning as defined in compound A2); (i) Compound C5a of compound C2 and, for example, salts thereof (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 1, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 132】 R β Q α Q β A β , R π and R μ (This has the same meaning as defined in compound A2); (j) Compound C5b of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 1, X α It is a halogen, 【Chemistry 133】 R β Q α Q β A β , R π and R μ (This has the same meaning as defined in compound A2); (k) Compound C5c of compound C2 and, for example, salts thereof (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 1, X α These are SPh and SePh, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 134】 R β Q α Q β A β , R π and R μ This has the same meaning as defined for compound A2. do); (l) Compound C6a of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 135】 R β Q α Q β , R π and R μ (This has the same meaning as defined in compound A2); (m) Compound C6b of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, X α It is a halogen, 【Transformation 136】 R β Q α Q β , R π and R μ (This has the same meaning as defined in compound A2); (n) Compound C7a of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 2, A β CH ２ And, X α SPh, SePh, SG α SeG α G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 137】 R β Q α Q β , R π and R μ (This has the same meaning as defined in compound A2); (o) Compound C7b of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(Q α ) Q β R μ And, A α is -N(R π ) - and nα is 2, A β CH ２ And, X α It is a halogen, 【Chemistry 138】 R β Q α Q β , R π and R μ (This has the same meaning as defined in compound A2); (p) Compound C8a of compound C2 and, for example, salts thereof (wherein, R α is -C(O)Q β R μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 139】 R β Q β , R π and R μ (This has the same meaning as defined in compound A2); (q) Compound C8b of compound C2 and, for example, salts thereof (in the formula, R α is -C(O)Q β R μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, X α is, N ＋ (O － ) (G α ) ２ And, [Chemical 140] R β Q β , R π and R μ (This has the same meaning as defined in compound A2); (r) Compound C9a of compound C2 and, for example, its salts as process intermediates and / or markers (wherein R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, X α SPh, SePh, SG α SeG α G α These are alkyl, haloalkyl, and phenyl, respectively; halogen group; alkyl group; and A phenyl compound substituted with 0 to 5 groups selected from haloalkyl groups, 【Chemistry 141】 R β , R π and R μ (This has the same meaning as defined in compound A2); (s) Compound C9b of compound C2 and, for example, salts thereof (wherein, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, X α These are SPh and SePh, 【Chemistry 142】 R β , R π and R μ (This has the same meaning as defined in compound A2); (t) Compound C9c of compound C2 and, for example, its salts as process intermediates and / or markers (wherein, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, X α It is a halogen, 【Chemistry 143】 R β , R π and R μ (This has the same meaning as defined in compound A2); (u) Compound C10 of compound C2 and its salt (wherein, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl, respectively; halogen group; alkyl group; and A phenyl compound substituted with 0 to 5 groups selected from haloalkyl groups, 【Chemistry 144】 R β , R π and R ζ (This has the same meaning as defined in compound A2); (v) Compound C11 of compound C2 and, for example, salts thereof (wherein, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from, R β is either unsubstituted or R ζ R is a phenyl ring substituted with up to five substituents independently selected from each of the following. λ And, X α These are SPh and SePh, 【Chemistry 145】 R π and R ζ (This has the same meaning as defined in compound A2); (w) Compound C12 of compound C2 and its salt (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to five substituents independently selected from each of the following. λ , X α These are SPh and SePh, 【Chemistry 146】 R ζ (This has the same meaning as defined in compound A2); (x) Compound C12a of compound C2 and its salt (wherein, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to five substituents independently selected from each of the following. λ , X α It is a halogen, 【Chemistry 147】 R ζ (This has the same meaning as defined in compound A2); (y) Compound C12b of compound C2 and its salt (wherein, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to five substituents independently selected from each of the following. λ , X α is, N ＋ (O － ) (G α ) ２ And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 148】 R ζ (This has the same meaning as defined in compound A2); (z) Compound C13 of compound C2 and its salt (wherein, R α is -C(O)NHR μ And, A α It is -NH-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to five substituents independently selected from each of the following. λ , X α SPh, SePh, SG α SeG α , N ＋ (O － ) (G α ) ２ And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 149】 R ζ (This has the same meaning as defined in compound A2); (aa) Compound C14 of compound C2 and its salt (wherein, R α is -C(O)NHR μ And, A α It is -NH-, nα is 2, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to five substituents independently selected from λ , X α SPh, SePh, SG α SeG α , N ＋ (O － ) (G α ) ２ And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. [Chemical 150] R ζ (This has the same meaning as defined for compound A); (bb) Compound C15 of compound C2 and its salt (wherein, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 2, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β = Non-substitution, or R ζ R is a phenyl ring substituted with up to five substituents independently selected from each of the following. λ , X α SPh, SePh, SG α SeG α , N ＋ (O － ) (G α ) ２ And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 151】 R ζ (This has the same meaning as defined in compound A2); (cc) one compound C16 from any of compounds C1 to C15 and, for example, a salt thereof. (In the formula, X α It is an SPh, R α , R β A α A β , nα and Q α (This has the same meaning as compound A2); (dd) one compound C16a from any of compounds C1 to C15 and, for example, a salt thereof. (In the formula, X α is N(Me) ２ And, R α , R β A α A β , nα and Q α (This has the same meaning as compound A2); (ee) Compound C16b having the following formula, 【Chemistry 152】 (ff) Compound C16c having the following formula, 【Chemistry 153】 (gg) Compound C16d having the following formula, 【Chemistry 154】 (hh) Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compounds C16e, 【Chemistry 155】 (ii) Compounds having the following structure for use as pesticides, preferably herbicide synthesis process intermediates and / or marker compound C16f, 【Chemistry 156】 (jj) Compounds for use as pesticides having the following structure, preferably herbicides and synthetic compounds Seth intermediate and / or marker compound C16g, 【Chemistry 157】 (kk) Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compound C16h, 【Chemistry 158】 (ll) Compound C17a having the following formula, 【Chemistry 159】 (mm) Compound C17b having the following formula, [Chemical 160] (nn) Compound C17c having the following formula, 【Chemistry 161】 (oo) Compound C17d having the following formula, 【Chemistry 162】 Compounds for use as pesticides having the following structure (pp), preferably herbicide synthesis process intermediates and / or marker compound C17f, 【Chemical 163】 (qq) Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compound C17g, 【Chemistry 164】 (rr) Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compound C17h, 【Chemistry 165】 (ss) Compounds for use as pesticides having the following structure, preferably herbicide synthesis process intermediates and / or marker compound C17i, 【Chemistry 166】 (tt) Compound C18a having the following formula, 【Chemistry 167】 (uu) Compound C18b having the following formula, 【Chemical 168】 (vv) Compound C19a having the following formula, 【Chemistry 169】 (lol) Compound C19b having the following formula, 【Chemistry 170】 (xx) Compound C20a having the following formula, 【Chemistry 171】 (yy) Compound C20b having the following formula, 【Chemistry 172】 (zz) Compound C21a having the following formula, 【Chemistry 173】 (aaa) Compound C21b having the following formula, 【Chemistry 174】 (bbb) Compound C22a having the following formula, 【Chemistry 175】 (ccc) Compound C22b having the following formula, 【Chemistry 176】 (ddd) Compound C23a having the following formula, 【Chemistry 177】 (eee) Compound C23b having the following formula, 【Chemistry 178】 (fff) Compound C24a having the following formula, 【Chemistry 179】 (ggg) Compound C24b having the following formula, 【Transformation 180】 (hhh) Compound C25a having the following formula, 【Chemistry 181】 (iii) Compound C25b having the following formula, 【Chemistry 182】 (jjj) Compound C26a having the following formula, 【Chemistry 183】 (kkk) Compound C26b having the following formula, 【Chemistry 184】 (lll) Compound C27a having the following formula, 【Chemistry 185】 (mmm) Compound C27b having the following formula, 【Chemical 186】 (nnn) Compound C28a having the following formula, 【Chemistry 187】 (ooo) Compound C28b having the following formula, 【Chemical 188】 (ppp) Compound C29a having the following formula, 【Chemical 189】 (qqq) Compound C29b having the following formula, 【Chemistry 190】 (rrr) Compound C30a having the following formula, 【Chemistry 191】 (sss) Compound C30b having the following formula, 【Chemistry 192】 (ttt) Compound C2, compound C31a and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 193】 R π and R ζ (This has the same meaning as defined in compound A2); (uuu) Compound C2, compound C31b and its salt (wherein, R α is -C(O)NHR μ And, A α is -N(R π ) - and nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is, X α It is a halogen, 【Chemistry 194】 R π and R ζ (This has the same meaning as defined in compound A2); (vvv) Compound C2, compound C32a and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is, X α SPh, SePh, SG α SeG α And, G α These are alkyl, haloalkyl, and phenyl, respectively; halogen group; alkyl group; and A phenyl compound substituted with 0 to 5 groups selected from haloalkyl groups, 【Chemistry 195】 R ζ (This has the same meaning as defined in compound A2); (lol) Compound C2, compound C32b and, for example, its salt (in the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 1, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is, X α It is a halogen, 【Chemistry 196】 R ζ (This has the same meaning as defined in compound A2); (xxx) Compound C2, compound C33 and, for example, salts thereof (wherein the formula, R α is -C(O)NHR μ And, A α It is -NH-, nα is 2, A β CH ２ And, Q α It is O, Q β NH is, R μ is an unsubstituted phenyl ring, or a phenyl ring substituted with up to five substituents independently selected from Rζ. R β H is, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 197】 R ζ (This has the same meaning as defined in compound A2); (yyy) Compound C2, compound C34 and, for example, salts thereof (in the formula, R α is -C(O)NHR μ And, A α is -N(Me)-, nα is 2, A β CH ２ And, Q α It is O, Q β NH is, R μ is either unsubstituted or R ζ A phenyl ring substituted with up to five substituents independently selected from each of the following: R β H is, X α SPh, SePh, SG α SeG α And, G α This refers to alkyl, haloalkyl, and phenyl compounds, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively. 【Chemistry 198】 R ζ (This has the same meaning as defined in compound A2); (zzz) Compound C35a, defined by any one of the following structures, 【Chemistry 199】 (In the formula, Q １ Q ２ , R １ , R ２ , R ３ , R ４ R6, Y1 and Y2, etc., have the meanings defined in claim 1 of PCT / US2014 / 068073, which was published as International Publication No. 2015 / 084796. X α =SPh、SePh、SG α 、SeG α G α = alkyl, haloalkyl, phenyl (phenyl substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively); (aaaa) Compound C36a defined by any one of the following structures, 【Chemistry 200】 (In the formula, Q, R １ Y and W have the meanings defined in claim 1 of PCT / US2020 / 034232, which was published as International Publication No. 2020 / 242946. X α =SPh, SePh, SG α SeG α , and G α = alkyl, haloalkyl, phenyl (phenyl substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively); (bbbb) Compound C37a defined by any one of the following formulas, 【Chemical Engineering 201】 (In the formula, Q １ Q ２ , R １ , R ２ , R ７ Y, A, and J, etc., have the meanings defined in claim 1 of PCT / US2016 / 030450, which was published as International Publication No. 2016 / 182780. X α SPh, SePh, SG α SeG α And, G α (These are alkyl, haloalkyl, and phenyl compounds, respectively, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups; respectively); (cccc) Compound C37b having any one of the following structures, for use as an intermediate and / or marker in the synthesis process of pesticides, preferably herbicides. 【Chemical Engineering 202】 (In the formula, Q １ Q ２ , R １ , R ２ , R ７ Y, A, and J, etc., have the meanings defined in claim 1 of PCT / US2016 / 030450, which was published as International Publication No. 2016 / 182780. X α SPh, SePh, SG α SeG α And, G α (These are alkyl, haloalkyl, and phenyl compounds, respectively, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups; respectively); (dddd) Compound C38 defined by any one of the following formulas, 【Chemical 203】 (In the formula, Q １ Q ２ , R Ｂ１ And X has the meanings defined in claim 1 of PCT / EP2020 / 052780, which was published as International Publication No. 2020 / 161147. X α SPh, SePh, SG α SeG α And, G α (These are alkyl, haloalkyl, and phenyl compounds, respectively, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups; respectively); (eeee) Compound C39 defined by one of the following formulas, 【Chemical 204】 (In the formula, Q, W ２ , R １ Y and Z, etc., have the meanings defined in claim 1 of PCT / EP2018 / 069001, which was published as International Publication No. 2019 / 025156. X α SPh, SePh, SG α SeG α And, G α (These are alkyl, haloalkyl, and phenyl compounds, respectively, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups; respectively); (ffff) Compound C40 defined by any one of the following formulas, 【Chemical 205】 (In the formula, Q １ Q ２ , R １ , R ７ , R ９ , J, L, Y and Y ２ "etc." has the meaning defined in claim 1 of PCT / US2018 / 035017, which was published as International Publication No. 2018 / 222647. X α SPh, SePh, SG α SeG α And, G α (These are alkyl, haloalkyl, and phenyl compounds, respectively, which are phenyl compounds substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups; respectively); (gggg) Compound C42 defined by one of the following formulas, 【Chemical 206】 (In the formula, Q １ Q ２ , R １ , R ７ , R ８ , R ９ J, Y, and W, etc., have the meanings defined in claim 1 of PCT / US2018 / 035015, which was published as International Publication No. 2018 / 222646. X α SPh, SePh, SG α SeG α And, G α (These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups; alkyl groups; and haloalkyl groups, respectively; and (hhhh) formula 【Chemical 207】 Compound C43 is defined by any one of the following: (In the formula, Q, W ２ , R １ , R ２ Y and Z, etc., have the meanings defined in claim 1 of PCT / EP2018 / 057628, which was published as International Publication No. 2018 / 184890. X α SPh, SePh, SG α SeG α And, G α (These are alkyl, haloalkyl, and phenyl compounds, each substituted with 0 to 5 groups selected from halogen groups, alkyl groups, and haloalkyl groups, respectively.)

15. A compound defined, illustrated, or described in Compound C16c.

16. A compound defined, illustrated, or described in compound C17a.

17. A process defined, illustrated, or described in any one of the following processes D1a; D1b; D2a; D2b; D3a; D3b; D3c; D4a; D4b; D5a; D5b; D6a; D6b; D7a; D7b; D8a; D8b; D9a; and D9b, or selected from the following: (a) A generally described process D1a for preparing an unsaturated precursor of formula 2 from a compound of formula 3, 【Chemical 208】 Meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ A process (wherein X) that includes oxidation of the corresponding compound of formula 3 using an oxidizing agent such as ) α , R α , R β A α A β , nα, and Q α Each of these has the same meaning as compound C1a); (b) The generally described above method for preparing the unsaturated precursor of formula 2 from the compound of formula 3 Rothes D1b, 【Chemical Engineering 209】 A process (wherein X) that includes an elimination reaction using an activator such as a base or Lewis acid. α , R α , R β A α A β , nα and Q α Each of these has the same meaning as compound C1a); (c) Dissolve the compound of formula 3 in a suitable solvent, such as acetic acid, and stir for the period exemplified for about 20 minutes (e.g., by stirring), and at a suitable temperature, add meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Process D2a of Process D1a, which includes adding small amounts of an oxidizing agent as exemplified by ).The reaction mixture is then stirred for a while at substantially the same temperature, for example, about 2 hours.The reaction mixture is then stirred, for example, NaHCO ３ The mixture can be quenched in aqueous solution and extracted typically twice with a suitable solvent. The combined organic layers can be concentrated to obtain the corresponding unsaturated precursor of formula 2; (d) Process D2b of Process D1a, comprising dissolving the compound of Formula 3 in a suitable solvent, for example chlorobenzene, stirring for a time exemplified by about 20 minutes (for example by stirring), and gradually adding an activator exemplified by a base or Lewis acid at a suitable temperature. The reaction mixture is then stirred for a while at substantially the same temperature, for example about 2 hours. The reaction mixture is then heated to, for example, NH ４ The mixture can be quenched in a Cl solution and extracted typically twice with a suitable solvent. The combined organic layers can be concentrated to obtain the corresponding unsaturated precursor of formula 2; (e) The following scheme 【Chemical 210】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemistry 211】 Process D3a, which includes the oxidation of the compound; (f) The following scheme 【Chemical Engineering 212】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor: 【Chemistry 213】 Process D3b, which includes oxidation of the compound; (g) The following scheme 【Chemical 214】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemical 215】 Process D3c, which includes the oxidation of the compound; (h) The following scheme 【Chemical 216】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemical 217】 Process D4a, which includes the oxidation of the compound; (i) The following scheme 【Chemical 218】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemical 219】 Process D4b, which includes the oxidation of the compound; (j) The following scheme 【Chemical 220】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemistry 221】 Process D5a, which includes the oxidation of the compound; (k) The following scheme 【Chemistry 222】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemistry 223】 Process D5b, which includes the oxidation of the compound; (l) scheme 【Chemistry 224】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemical 225】 Process D6a, which includes the oxidation of the compound; (m) The following scheme 【Chemistry 226】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemistry 227】 Process D6b, which includes oxidation of the compound; (n) scheme 【Chemistry 228】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemistry 229】 Process D7a, which includes the oxidation of the compound; (o) The following scheme 【Chemistry 230】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemistry 231】 Process D7b, which includes oxidation of the compound; (p) The following scheme 【Chemistry 232】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemical 233】 Process D8a, which includes the oxidation of the compound; (q) The following scheme 【Chemistry 234】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemical 235】 Process D8b, which includes the oxidation of the compound; (r) The following scheme 【Chemistry 236】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemistry 237】 Process D9a, which includes the oxidation of the compound, and (s) scheme 【Chemical 238】 Processes exemplified by the following, which involve meta-chloroperoxybenzoic acid (mCPBA) or hydrogen peroxide (H ２ O ２ Using the oxidizing agent exemplified by ), the following formula is used to obtain the corresponding unsaturated precursor compound: 【Chemistry 239】 Process D9b involves the oxidation of the compound.

18. For use as an intermediate in the method for preparing the corresponding saturated target of Equation 1, 【Chemistry 240】 (In the formula, R α , R β A α A β , nα and Q α This has the same meaning as defined in compound A2, and R δ and R γ (This has the same meaning as defined in process B.) Compounds defined, illustrated, or described in Compound E1, or Compound E1 of formula 4, and, for example, its salts. 【Chemistry 241】

19. A process defined, illustrated, or described in any one of the following processes F1a; F1b; F1c; F2a; F2b; F3; and F4, or selected from the following group: (a) A process F1a for preparing the compound of formula 3 from the compound of formula 4, 【Chemistry 242】 X obtained by using bases and electrophiles α Includes the addition of a "leaving" group, X α , R α , R β A α A β , nα and Q α Each of these represents the same meaning as compound C1a, in a process; (b) A process F1b for preparing the compound of formula 3 from the compound of formula 4, 【Chemistry 243】 X is produced by using a leaving group source such as a halogenating reagent. α Including the addition of a leaving group, X α , R α , R β A α A β , nα and Q α Each of these has the same meaning as compound C1a, in the process; (c) A process F1c for preparing the compound of formula 3 from the compound of formula 4, 【Chemistry 244】 X obtained by using bases and electrophiles α Including the addition of a base, X α , R α , R β A α A β , nα and Q α Each of these represents the same meaning as compound C1b, a process; (d) Process F2a of Process F1a, comprising: dissolving the compound of Formula 4 in a suitable solvent containing a base such as sodium hydride at a specified temperature for a time typically exemplified by cooling and stirring (e.g., stirring) for about 20 minutes; adding an electrophile exemplified by diphenyl disulfide; phenyl hypochlorite; or phenyl hypobromite, dissolved in a suitable solvent at substantially the same temperature; and stirring the reaction mixture for a while at substantially the same temperature. ４ Quench in Cl solution, extract typically two or more times with a suitable solvent, wash the combined organic layer with Na ２ SO ４ By drying and concentrating, the corresponding compound of formula 3 can be obtained; (e) Process F2b of Process F1b, comprising dissolving the compound of Formula 4 together with a leaving group exemplified by a halogenating reagent (e.g., a bromine source) in a suitable solvent at a specific temperature, and optionally adding a base and / or a catalyst (catalytic components including one or more of a catalyst; pre-catalyst; and co-catalyst). Quenching the reaction mixture by stirring (e.g., by stirring) at substantially the same temperature for about 2 hours, and extracting it with a suitable solvent. Preferably, the mass is washed again, and / or the combined layer is washed, and optionally, for example, Na ２ SO ４ It is dried and concentrated to obtain the corresponding compound of formula 3; (f) Process F3, which is either process F2a or F2b, further comprising purifying the compound of formula 3 obtained from the above process, and (g) Process F4, one of processes F1 to F3, using either diphenyl disulfide or phenyl hypochlorite as the electrophile.

20. Compounds defined as, illustrated, or described as any one of the following: G1; G2; DD1; DD2; DD3; DD4; DD5; DD6; DD7; DD8; DD9; DD10; and DD11, or selected from the following group: (a) A preservation marker G1 having the following structure, and, for example, a salt thereof, 【Chemistry 245】 (In the formula, R β Q α Q β and R π (This has the same meaning as defined in compound A2); (b) Conservation marker compound G2 of formula D obtained by exposing tetoflupyrrolimeth to sunlight 【Chemistry 246】 (c) Conservation marker compound DD1 of the following formula, 【Chemistry 247】 (In the formula, R β Q α A β A α (and nα have the same meaning as defined in compound A2); (d) Conservation marker compound DD2 of the following formula, 【Chemistry 248】 (In the formula, R β Q α A β and R π (This has the same meaning as defined in compound A2); (e) Conservation marker compound DD3 of the following formula, 【Chemistry 249】 (In the formula, R π and R ζ (This has the same meaning as defined in compound A2); (f) Conservation marker compound DD4 of the following formula, [Chemical 250] (In the formula, R β Q α A β and R π (This has the same meaning as defined in compound A2); (g) Conservation marker compound DD5 of the following formula, 【Chemistry 251】 (In the formula, each R ζ (This has the same meaning as defined in compound A2); (h) Conservation marker compound DD6 of the following formula, 【Chemistry 252】 (i) Conservation marker compound DD7 of the following formula, 【Chemistry 253】 (j) Conservation marker compound DD8 of the following formula, 【Chemistry 254】 (k) Conservation marker compound DD9 of the following formula, 【Chemistry 255】 (l) The following conservation marker compound DD10, 【Chemistry 256】 and (m) The storage marker compound DD11 of the following formula. 【Chemistry 257】

21. Conservation marker compounds defined as, illustrated, or described by any one of the following compounds: G1; G2; DD1; DD2; DD3; DD4; DD5; DD6; DD7; DD8; DD9; DD10; and DD11, or selected from the following group: (a) A preservation marker G1 having the following structure, and, for example, a salt thereof, 【Chemistry 258】 (In the formula, R β Q α Q β and R π (This has the same meaning as defined in compound A2); (b) Conservation marker compound G2 of formula D obtained by exposing tetoflupyrrolimeth to sunlight 【Chemistry 259】 (c) Conservation marker compound DD1 of the following formula, 【Chemical 260】 (In the formula, R β Q α A β A α (and nα have the same meaning as defined in compound A2); (d) Conservation marker compound DD2 of the following formula, 【Chemistry 261】 (In the formula, R β Q α A β and R π (This has the same meaning as defined in compound A2); (e) Conservation marker compound DD3 of the following formula, 【Chemistry 262】 (In the formula, R π and R ζ (This has the same meaning as defined in compound A2); (f) Conservation marker compound DD4 of the following formula, 【Chemical 263】 (In the formula, R β Q α A β and R π (This has the same meaning as defined in compound A2); (g) Conservation marker compound DD5 of the following formula, 【Chemistry 264】 (In the formula, each R ζ (This has the same meaning as defined in compound A2); (h) Conservation marker compound DD6 of the following formula, 【Chemical 265】 (i) Conservation marker compound DD7 of the following formula, 【Chemical 266】 (j) Conservation marker compound DD8 of the following formula, 【Chemistry 267】 (k) Conservation marker compound DD9 of the following formula, 【Chemical 268】 (l) The following conservation marker compound DD10, 【Chemistry 269】 and (m) The storage marker compound DD11 of the following formula. 【Chemistry 270】

22. A conservation marker compound defined, illustrated, or described as compound G2.

23. A process defined, illustrated, or described in any one of processes H1; H2; H2a; H3; H4; H5; and H6, or a process selected from the following group: (a) A process H1 for preparing a storage marker compound from a corresponding saturated target compound in the following general scheme, wherein the saturated target is exposed to sunlight for a sufficient time to form a detectable amount of the corresponding storage marker when measured by analytical methods exemplified by HPLC and particularly HPLC-MS: 【Chemistry 271】 (In the formula, R β A β A α , R ζ (and nα have the same meaning as defined in compound A2); (b) Process H2 for preparing a conserved marker compound from a corresponding saturated target compound in the following general scheme, 【Chemistry 272】 A process comprising exposing a composition, such as a saturated target solution, to sunlight for a sufficient time to form a detectable amount, particularly an amount exceeding the limit of quantification, of the corresponding storage marker in the composition, using analytical techniques exemplified by HPLC-MS; (c) Process H2a for preparing a corresponding conserved marker compound from a saturated target compound which is (3S,4S)-2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide, in the following scheme, 【Chemistry 273】 A process comprising exposing a composition such as a solution of (3S,4S)-2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide to sunlight for a time sufficient to form a detectable amount, particularly an amount exceeding the limit of quantification, of the corresponding storage marker in the composition, using analytical techniques exemplified by HPLC-MS; (d) Process H3, which includes either process H2 or H2a, wherein the composition is maintained at a predetermined level of pH acidity / basicity, preferably by a method exemplified by including an appropriate buffer in the aqueous solution: (e) Process H4 of Process H3, wherein the saturated target solution is maintained at acidity / basicity levels exemplified by the saturated target aqueous solution having a pH selected from about 4±1; 7±1; and 10±1, preferably by including an effective concentration of appropriate buffer in the aqueous solution; (f) Process H5, one of processes H2; H2a; H3; and H4, wherein the rate at which the corresponding storage marker is formed from the saturated target compound by exposure to sunlight is further mediated by the selection of the acidity / basicity of the composition containing the saturated target, and (g) Process H6, which is one of processes H3, H4, and H5, wherein the composition is an aqueous solution, and the rate at which the corresponding storage marker is formed from the saturated target upon exposure to sunlight is mediated by the selection of the pH of the aqueous solution of the saturated target.

24. Any one of the processes H7; H8; H9; H10; H11; and H12 is defined, illustrated, or described, or is selected from the following group: (a) A process H7 for minimizing the conversion rate of 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide in the composition to the corresponding storage marker, comprising minimizing and / or avoiding exposure of the composition to sunlight and / or mitigating the conversion effect of such exposure to sunlight; (b) A process H8 for minimizing the conversion rate of tetoflupyrrolimeth in the composition to the corresponding storage marker, comprising minimizing the time and extent of exposure of the composition to sunlight and / or mitigating the conversion effect of such exposure to sunlight; (c) A process H9 for minimizing the conversion rate of tetoflupyrrolimeth in the composition to the corresponding storage marker, comprising including in the composition a component; an excipient; an adjuvant; a carrier; or any additive that can reduce at least one of the conversion effects of exposure to sunlight, or that can reduce the rate at which the conversion occurs with exposure to sunlight in the absence of the component, excipient, adjuvant, carrier, or additive; (d) A process H10 for minimizing the conversion rate of tetoflupyrrolimeth in a product containing a tetoflupyrrolimeth composition (including a solution thereof) to a corresponding preservation marker during the manufacture, packaging, labeling, transport and storage of the product, comprising mitigating or overcoming the effects of exposure to sunlight of the product by including the composition in lightfast, preferably substantially opaque packaging and / or containers (e.g., container-closure systems) that protect the contents from the conversion effects of sunlight by specific properties of the materials comprising them, including by lightfast or opaque coating, or by the use of secondary packaging, or by including any coating applied thereto, including a transparent, colorless, or translucent container that has been made lightfast in an amber container, wherein lightfastness and opacity are related to the wavelength of light that mediates the conversion of tetoflupyrrolimeth to a corresponding preservation marker; (e) Process H11 and / or composition of any one of Processes H1 to H10 in which the saturated target compound, preferably tetoflupyrrolimeth, is present in a liquid, solution, emulsion or suspension composition, and (f) A process H12 for minimizing the rate at which an aqueous solution of tetoflupyrrolimeth is converted to a corresponding storage marker compound when the solution is exposed to sunlight, the process comprising maintaining the pH of the aqueous solution in the range of about 6 to about 8, preferably about 7.

25. A process defined, illustrated, or described in any one of processes H13; H14; H15; and H16, or a process selected from the following group: (a) A process H13 for determining the period during which a storage composition containing a saturated target compound, particularly a tetoflupyrrolimeth composition, has been exposed to sunlight during storage, comprising: measuring and quantifying the relative content of a corresponding storage marker compound compared to the content of a saturated target in the composition; and evaluating the period of exposure to sunlight by referring to a standard calibration conversion rate in one or more reference compositions containing a saturated target compound; (b) Process H14 of Process H13, wherein the measurement and quantification of the relative content is exemplified by calculating the ratio of the respective areas under the decomposed characterizing peaks of each compound in the test sample by appropriate HPLC analysis; (c) Process H15 of either process H13 and H14, in which the standard calibration rate is determined for a reference composition having the same acidity / basicity as the stored test composition, and (d) Process H16 of any one of processes H13, H14, and H15, wherein the standard calibration rate is determined for a reference composition packaged in the same container system as the stored test composition.

26. A preservative packaging composition defined, illustrated, or described in any one of compositions I1; I2; I3; I4; I5 and I13, or selected from the following group: (a) Preservation packaging composition I1 comprising a combination of a detectable amount of a preservation marker compound and the corresponding saturated target compound to which it is converted, as exemplified by the process of process H2; (b) In particular, the following formula 【Chemistry 274】 The following formulas, including any isomer or enantiomer thereof, are exemplified by (3S,4S)-2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide. 【Chemistry 275】 Combined with the saturated target compound, the following formula 【Chemistry 276】 A storage packaging composition I2 of composition I1 containing a detectable, preferably measurable, amount of a storage marker compound; (c) A storage packaging composition I3 of either composition I1 or I2, comprising a saturated target solution, particularly an aqueous solution, maintained at a predetermined level of acidity / basicity, preferably pH, by a method exemplified by preferably including a suitable buffer system in an aqueous solution; (d) The storage packaging composition I4 according to composition I3, wherein the saturated target solution is maintained at the acidity / basicity level exemplified by the saturated target aqueous solution having a pH selected from about 4 ± 1; about 7 ± 1; and about 10 ± 1, by preferably including a suitable buffer in an aqueous solution at a concentration effective to maintain the acidity / basicity level, and (d) Conservation marker compounds, especially those of the following formula 【Chemistry 277】 The compound, upon exposure to sunlight during storage, is released from the corresponding saturated target, particularly according to the following formula. 【Chemistry 278】 A storage packaging composition I5 of any one of compositions I1 to I4, wherein the rate of formation from the compound is further mediated by the selection of the acidity / basicity of the saturated target composition over the storage period; (e) A storage packaging composition I13 comprising a saturated target compound, comprising a corresponding storage marker compound in a measurable amount, preferably in a detectable amount, after storage in a sunlight environment for a period of more than two months.

27. A packaged aqueous composition of tetoflupyrrolimeth as defined and described in Composition I6, or A packaged aqueous composition I6 of tetoflupyrrolimeth, wherein the tetoflupyrrolimeth comprises any isomer, enantiomer, or mixture thereof when the composition is exposed to sunlight during storage, and the following formula 【Chemistry 279】 A tetoflupyrrolimeth packaging aqueous composition characterized in that the rate at which it is converted to the corresponding storage marker is minimized, and the composition is adapted to maintain a pH in the range of about 6 to about 8, preferably about 7, during storage by including in the composition components, excipients, or other components exemplified by a buffer or buffer system.

28. Agricultural products defined, illustrated, or described in either Product I7 or I8, or selected from the following group: (a) An agricultural product comprising a composition of 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide, particularly tetoflupyrrolimeth, comprising any isomer, enantiomer or mixture thereof that occurs during storage, the following formula 【Chemistry 280】 The rate of conversion of to the corresponding storage marker is minimized, and the product is adapted to limit, reduce, minimize, or substantially avoid the time and extent of exposure of the composition in the product to sunlight during storage, and the minimization is compared to agricultural tetoflupyrrolimeth products without such adaptation, as in agricultural product I7, and (b) During the manufacture, packaging, labeling, transport or storage of the tetoflupyrrolimeth composition, the following formula, 【Chemistry 281】 An agricultural product comprising the composition, which is protected to a detectable degree against sunlight-mediated conversion to a corresponding storage marker compound. Agricultural product I8, characterized in that the product comprises the composition, which is contained in a substantially lightfast, preferably opaque, packaging and / or container-closure system that protects the contents from the effects of sunlight, including by an opaque cover, by the use of secondary packaging, or by any coating applied thereto, including a transparent, colorless, or translucent container that has been made lightfast in an amber container.

29. A composition defined, illustrated, or described in either Product I7 or I8, or selected from the following: (a) An agricultural product comprising a composition of 2'-fluoro-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxanilide, particularly tetoflupyrrolimeth, comprising any isomer, enantiomer or mixture thereof that occurs during storage, the following formula 【Chemistry 282】 The rate of conversion of to the corresponding storage marker is minimized, and the product is adapted to limit, reduce, minimize, or substantially avoid the time and extent of exposure of the composition in the product to sunlight during storage, and the minimization is compared to agricultural tetoflupyrrolimeth products without such adaptation, as in agricultural product I7, and (b) During the manufacture, packaging, labeling, transport or storage of the tetoflupyrrolimeth composition, 【Chemistry 283】 An agricultural product comprising the composition, which is protected to a detectable degree against sunlight-mediated conversion to a corresponding storage marker compound. Agricultural product I8, characterized in that the product comprises the composition, which is contained in a substantially lightfast, preferably opaque, packaging and / or container-closure system that protects the contents from the effects of sunlight, including by an opaque cover, by the use of secondary packaging, or by any coating applied thereto, including a transparent, colorless, or translucent container that has been made lightfast in an amber container.

30. Defined and illustrated in any one of compositions I9; I10; and I12, or The following tetoflupyrrolimeth compositions are described or selected from the following: (a) The following formula 【Chemistry 284】 A tetoflupyrrometh composition I9 characterized by a minimized proportion or degree of photocatalytic conversion of tetoflupyrrometh to a corresponding storage marker, A composition comprising at least one of the following components, excipients, adjuvants, carriers, or additives that can reduce the conversion effect of exposure to sunlight, or that can reduce the rate at which the conversion occurs upon exposure to sunlight in the absence of the aforementioned component, excipient, adjuvant, carrier, or additive; (b) A tetoflupyrrolimeth composition I10 that is stabilized to at least a measurable extent against photocatalytic conversion to a corresponding preservation marker during manufacturing, packaging, labeling, transport and storage, wherein the composition comprises at least one of the components, excipients, adjuvants, carriers or additives that can reduce the conversion effect of exposure to sunlight and / or reduce the rate at which the conversion occurs without the component, excipient, adjuvant, carrier or additive, and (c) A tetoflupyrrolimeth composition I12 that is at least measurably stabilized for conversion to a corresponding preservation marker, or exhibits a measurably reduced conversion rate to a corresponding preservation marker during manufacturing, packaging, labeling, transport and storage, wherein the composition is compared to the standard calibrated conversion rate of one or more reference compositions containing tetoflupyrrolimeth, i) A buffer solution that maintains the pH of the composition at 7 ± 1; ii) UV absorbers; iii) Suitable dyes, colorants, or pigments include components that exhibit substantially the same absorption spectrum as tetoflupyrrolimeth; iv) Components, etc., that can reduce the amount of sunlight hitting the material; v) Milking agents; vi) Reflective pigments such as titanium dioxide; vii) A photoprotective coating covering at least a portion of the tetoflupyrrolimeth in the composition; viiii) A composition comprising at least one component which is any, some or all of the following: a complex of tetoflupyrrolimeth with a complexing agent, for example, an inclusion complex with a cyclodextrin; the reference composition comprising tetoflupyrrolimeth which does not contain the aforementioned components.

31. Products defined, illustrated, or described in either Product I11 or I15, or selected from the following: (a) Product I11 comprising a tetoflupyrrolimeth composition that is shielded from sunlight-mediated conversion to a corresponding preservation marker during any of the following: manufacture; packaging; labeling; transport; or storage of the composition, wherein the product comprises the tetoflupyrrolimeth composition contained in substantially lightfast, preferably opaque, packaging, as substantially described in process H10. and (b) A product of any one of compositions I1 to I12 and / or composition I15, wherein the saturated target is preferably tetoflupyrrolimeth in a liquid, solution, emulsion, or suspension composition.

32. Buffered tetoflupyrrolimeth composition defined, illustrated, or described in composition I14 object, or A buffered tetoflupyrrolimeth composition containing a corresponding storage marker compound in a measurable amount, preferably in a detectable amount, after storage in a sunlight environment for a period equal to or longer than two months.

33. Crystalline polymorph I of N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide or tetoflupyrrolimeth, defined by either one of the crystal polymorphs J1 or J2, or selected from the following group: (a) Crystalline polymorph J1, form I of N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide exhibiting at least one of the following properties: The infrared spectrum shown in Figure 9 is essentially... The powder X-ray diffraction pattern shown in Figure 5 is essentially the same. Powder X-ray diffraction pattern with a differential peak at 9.6 at 2θ (±0.20), Powder X-ray diffraction patterns having at least four characteristic peaks at 2θ (±0.20) at 9.6, 15.0, 17.3, 17.9, 21.6 and 24.6, and (b) Crystal polymorph J2 of tetoflupyrrolimete, morphology I, exhibiting at least one of the following properties: The infrared spectrum shown in Figure 9 is essentially... The powder X-ray diffraction pattern shown in Figure 5 is essentially the same. Powder X-ray diffraction pattern with a differential peak at 9.6 at 2θ (±0.20), Powder X-ray diffraction pattern having at least four characteristic peaks at 2θ (±0.20) at 9.6, 15.0, 17.3, 17.9, 21.6, and 24.

6.

34. Composition J3; a composition defined by either J4 or J5, or selected from the following group: (a) Composition J3 comprising tetoflupyrrolimeth in crystalline polymorph form I, defined by either crystalline polymorph J1 or J2; (b) A pesticide, preferably herbicidal composition J4, comprising one of the crystalline polymorph forms I of crystalline polymorphs J1 and J2, and a herbicidally acceptable diluent or carrier, and (c) A pesticide composition, preferably a herbicide composition J5, prepared from one of the crystalline polymorphs J1 and J2, morph I.

35. Polymorph II of N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide or tetoflupyrrolimeth, defined by either one of crystalline polymorphs K1 or K2, or selected from the following group: (a) Crystalline polymorph K1, form II of N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide exhibiting at least one of the following properties: The infrared (IR) absorption spectrum shown in Figure 10 is essentially the same as shown here. An infrared (IR) absorption spectrum having at least one characteristic peak selected from values ​​expressed as cm⁻¹ (±1 cm⁻¹) at 1678, 1546, 1395, 946, 924, 885, 825 and 662, The powder X-ray diffraction pattern shown in Figure 6 is essentially the same. Powder X-ray diffraction pattern having a differential peak represented by 2θ (±0.20) at 6.9, The following: Powder X-ray diffraction patterns having at least four characteristic peaks represented by 2θ (±0.20) selected from the values ​​of 6.9, 11.2, 17.7, 23.5 and 26.3, and (b) Polymorph K2, form II of tetoflupyrrolimete exhibiting at least one of the following properties: The infrared (IR) absorption spectrum shown in Figure 10 is essentially the same as shown here. An infrared (IR) absorption spectrum having at least one characteristic peak selected from values ​​expressed as cm⁻¹ (±1 cm⁻¹) at 1678, 1546, 1395, 946, 924, 885, 825 and 662, The powder X-ray diffraction pattern shown in Figure 6 is essentially the same. Powder X-ray diffraction pattern having a differential peak represented by 2θ (±0.20) at 6.9, The following is a powder X-ray diffraction pattern having at least four characteristic peaks represented by 2θ (±0.20) selected from the values ​​6.9, 11.2, 17.7, 23.5, and 26.

3.

36. Amorphous solid form of N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide or tetoflupyrrolimeth, prepared by a process exemplified by one of the following: precipitation; spray drying; freeze-drying; adsorption in or onto a solid carrier; solid solution in a polymer, wax, sugar, or salt, and complex formation with a polyelectrolyte or cyclodextrin.

37. A combination of solid forms of N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide or tetoflupyrrolimeth, comprising crystalline polymorph I of the compound; crystalline polymorph II; and at least two selected from the group of crystalline polymorph II.

38. Composition K3; a composition defined by either K4 or K5, or selected from the following group: (a) Composition K3 containing crystalline polymorph form II, which is either crystalline polymorph K1 or K2. (b) A pesticide comprising a crystalline polymorph II, which is one of crystalline polymorphs K1 and K2, and a diluent or carrier that is pesticide-, preferably herbicidal-, acceptable, preferably herbicidal composition K4, and (c) A pesticide composition, preferably a herbicide composition K5, prepared from crystalline polymorph II, which is one of crystalline polymorphs K1 and K2.

39. Preparation methods defined and / or described in Method K6 and K6a, or any one selected from the following group: (a) A crystallization method for preparing crystalline polymorphism I, which is one of crystalline polymorphisms J1 and J2, including recrystallization from tert-butylmethyl ether, K6, (b) A method K6a for preparing a crystalline polymorph I with one of crystalline polymorphs J1 and J2, i) Dissolve (3R,4S)-1-methyl-2-oxo-4-(3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylic acid in acetonitrile (200 mL), ii) Adding 2-fluoroaniline and N-methylimidazole, iii) Mix the obtained contents at ambient temperature for a period of time exemplified by 10 minutes, iv) Adding chloro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate, v) Stir the resulting mixture at ambient temperature for a period of time exemplified by 10 hours, vi) For example, removing the solvent by evaporation, vii) The residue dissolves in dichloromethane, viiii) For example, washing with aqueous sodium sulfate solution and brine, ix) Drying and concentrating under reduced pressure to obtain a crude product, x) A method comprising recrystallizing the crude product from tert-butyl methyl ether.

40. Preparation methods defined and / or described in Method K7, and K7a or any one selected from the following group: (a) A method for preparing crystalline polymorphisms II and K7 using one of crystalline polymorphisms K1 and K2, the method comprising heptane trituration, and (b) A method for preparing a crystalline polymorph II K7a based on one of crystalline polymorphs K1 and K2, i) Dissolving N-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide in diethyl ether, ii) For example, CuBr. SMe ２ Adding and iii) For example, adding 2,2'-bis(diphenylphosphine)-1,1'-binaphthalene, iv) Stir the reaction mixture for a period of 20 minutes as shown, v) Cooling the reaction mass, vi) For example, adding trimethylsilyltrifluoromethanesulfonate, vii) Stir for 20 minutes, viiii) Adding magnesium 3-(trifluoromethyl)phenyl)bromide, ix) Stir for the period of two hours as exemplified, x) The reaction mass is, for example, NH ４ Quenching in an aqueous Cl solution, xi) Extraction with ethyl acetate, xi) Wash the combined organic layer with brine solution, xiiii) Na ２ SO ４ The process involves drying and concentrating the product to obtain a crude product, xiv) For example, purification by column chromatography using ethyl acetate / hexane (20:80) as the eluent, xv) A method comprising triturating the obtained solid with heptane (5 mL).

41. A procedure defined, illustrated, or described in either procedure N1 or N2, or selected from the following group: (a) General procedure N1 for preparing storage markers from saturated targets: 【Chemical 285】 (In the formula, R β A β A α and R ζ (This has the same meaning as defined in compound A2.) (b) General procedure N2 for preparing storage markers useful for pH-dependent calibration, based on three aqueous compositions of saturated targets, each buffered at a different pH: Three lots of approximately 50 mg of saturated target were each suspended in approximately 2 ml of 2% acetonitrile aqueous solution and subjected to sonication for approximately 20 minutes. Add approximately 0.1 ml of one of three different buffer solutions to pH=4, pH=7, and pH=10, respectively. The three buffer solutions mentioned above are filtered and introduced into quartz tubes, and exposed to natural sunlight for approximately two months. Analysis by HPLC-MS reveals the formation of corresponding storage markers in solutions of pH-related concentrations.

42. Compounds defined, illustrated, or described in any one of the following: P1; P1a; P2; P2a; P3; P3a; Q1; Q2; and Q3, or compounds selected from the following: (a) Compound P1 of the following formula 【Chemistry 286】 or its salt or N-oxide (In the formula, Each R ζ (This has the same meaning as defined in compound A2); (b) Synthetic intermediate compound P1a for preparing the saturated target of the following formula, 【Chemistry 287】 or its salt or N-oxide (in the formula, R ζ (This has the same meaning as defined in compound A2); (c) Compound P2 of the following formula 【Chemical 288】 or its salt or N-oxide; (d) Synthetic intermediate compound P2a for preparing the saturated target of the following formula, 【Chemistry 289】 or its salt or N-oxide; (e) Compound P3 of the following formula 【Chemistry 290】 or its salt or N-oxide; (f) Synthetic intermediate compound P3a for preparing the saturated target of the following formula, 【Chemistry 291】 or its salt or N-oxide; (g) Compound Q1 of the following formula 【Chemistry 292】 or its salt or N-oxide (In the formula, Each R ζ (This has the same meaning as defined in compound A2); (h) Compound Q2 of the following formula 【Chemistry 293】 or its salt or N-oxide; and (i) Compound Q3 of the following formula 【Chemistry 294】 or its salt or N-oxide.

43. Processes, methods, or synthesis defined, illustrated, or described in any one of Preparations A; B; C; D1; D2; D3; D4; E; F; G; H; I; J; K; L; M; N; O; P; Q; R; S; T; U; V; W; X; Y; Z; AA; AB; AC; AD; AE; AF; AG; AH; AI; AJ; AK; AL; and AM.

44. One of the unsaturated precursors of compounds A1 to A35, Process B15a, used as an intermediate in a method for preparing a saturated target as defined in any one of processes B1 to B14.

45. Process B15c, comprising the use of one of the unsaturated precursors of process B1 as an intermediate in a method for preparing a saturated target in any one of processes B1 to B14.

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