Pyrazole amide insecticides

Abstract

Compounds having Formula 1 are disclosed, and A, R1, R2, R3, R4, R5, Q, and X are as defined in the disclosure. Also disclosed are compositions containing these compounds of Formula 1, and methods for controlling and combating an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention. # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of U.S. Provisional Application No. 63 / 409,393, filed on September 23, 2022. Technical Field

[0003] The present invention relates to novel pyrazole compounds and compositions suitable for agronomic and non-agronomic uses, and methods of their use for controlling or combating invertebrate pests, such as arthropods, in both agronomic and non-agronomic settings. Background Art

[0004] The control of invertebrate pests is extremely important in achieving high crop efficiency. The damage of invertebrate pests to growing and stored crops can cause productivity to significantly reduce, and thus cause the cost of the consumer to increase. The control of invertebrate pests is also important in forestry, greenhouse crops, ornamental plants, nursery crops, stored food and fiber products, families, turf, timber products and public health. For these purposes, many products are commercially available, but continue to need more effective, less costly, less toxic, safer to the environment or novel compounds with different action sites. Summary of the Invention

[0005] The present disclosure relates to compounds having Formula 1 (including all geometric isomers and stereoisomers), N-oxides and salts thereof, and compositions containing them, and their use for controlling and combating invertebrate pests:

[0006]

[0007] in,

[0008] X is O or S;

[0009] Each A is independently CH, N or CR 1 ;

[0010] Each R 1 are independently H, amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or each R 1is independently phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replace; or each R 1 are independently C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0011] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6 substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replacement; or R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0012] R 3 is C1-C3 alkyl or C1-C3 haloalkyl;

[0013] R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 4 It is C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ;

[0014] R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 5 It is C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0015] R 6 are independently halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or S(=NR)O p R 7 ;

[0016] R 7 are independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 12 Replacement; or R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace;

[0017] R 8 are independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0018] When R 7 and R 8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 ;

[0019] R 9 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl are each optionally substituted by one or more R 6 Replacement; or R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0020] Each R 10are independently H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0021] Each R 11 are independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0022] R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, wherein alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted with halogen or cyano;

[0023] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace;

[0024] n is 1, 2, or 3;

[0025] p is 0, 1, or 2.

[0026] The present invention also provides a composition comprising a compound of formula 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent. In one embodiment, the present invention also provides a composition for controlling and combating invertebrate pests, comprising a compound of formula 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising at least one additional biologically active compound or agent.

[0027] The present invention provides a method for controlling and combating invertebrate pests, the method comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein). The present invention also relates to such methods, wherein the invertebrate pest or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising a biologically effective amount of at least one additional biologically active compound or agent.

[0028] The present invention also provides a method for protecting seeds from invertebrate pests, the method comprising contacting the seeds with a biologically effective amount of a compound having Formula 1 (eg, as a composition described herein). The present invention also relates to the treated seeds.

[0029] The present invention also provides a method for increasing the vigor of a crop plant, comprising contacting the crop plant, a seed from which the crop plant grows, or the locus of the crop plant (e.g., a growing medium) with a biologically effective amount of a compound having Formula 1 (e.g., as a composition described herein). DETAILED DESCRIPTION

[0030] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," "characterized by," or any other variations thereof, are intended to cover a non-exclusive inclusion, subject to any limitation expressly stated. For example, a composition, mixture, process, or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process, or method.

[0031] The transitional phrase "consisting of" excludes any unrecited element, step, or ingredient. If included in a claim, this phrase renders the claim closed, excluding materials other than those recited, except for impurities normally associated therewith. When the phrase "consisting of" appears in a clause of the body of a claim rather than immediately following the preamble, the phrase limits only the elements recited in that clause; the claim as a whole does not exclude other elements.

[0032] The transitional phrase "consisting essentially of is used to define compositions or methods that include materials, steps, features, components, or elements other than those literally disclosed, provided that such additional materials, steps, features, components, or elements do not materially affect one or more of the basic and novel characteristics of the claimed invention. The term "consisting essentially of is intermediate between "comprising" and "consisting of."

[0033] When the applicants have defined the invention or a portion thereof using open-ended terms such as "comprising," it should be readily understood that (unless otherwise indicated) the specification should be interpreted as also describing the invention using the terms "consisting essentially of" or "consisting of."

[0034] Furthermore, unless expressly stated otherwise, "or" refers to an inclusive or rather than an exclusive or. For example, condition A or B is satisfied by any 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).

[0035] In addition, the indefinite articles "a" and "an" before an element or component of the present invention are intended to be non-restrictive with respect to the number of instances (i.e., occurrences) of the element or component. Thus, "a" or "an" should be interpreted to include one or at least one, and the singular word form of an element or component also includes the plural unless the number clearly indicates a singular number.

[0036] As referred to in this disclosure, the term "invertebrate pests" includes arthropods, gastropods, nematodes, and worms that are economically important as pests. The term "arthropod" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs, and symphylans. The term "gastropod" includes snails, slugs, and other members of the order Stylommatophora. The term "nematode" includes members of the phylum Nematoda.

[0037] In the context of the present disclosure, "invertebrate pest control" means the inhibition of development (including mortality, feeding reduction, and / or mating disruption) of invertebrate pests, and related expressions are similarly defined.

[0038] The term "agronomy" refers to the production of field crops such as for food and fiber, and includes maize or corn, soybeans and other legumes, rice, cereals (e.g., wheat, oats, barley, rye, and rice), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, peppers, eggplant, crucifers, and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone, and citrus), small fruits (e.g., berries and cherries), and other specialty crops (e.g., canola,

[0039] sunflower and olives).

[0040] The term "non-agricultural" refers to applications other than field crops, such as horticultural crops (e.g., greenhouse, nursery, or ornamental plants not grown in the field), residential, agricultural, commercial, and industrial structures, turf (e.g., sod farms, pastures, golf courses, lawns, athletic fields, etc.), wood products, storage products, agroforestry and vegetation management, and public health applications.

[0041] The term "crop vigor" refers to the growth rate or biomass accumulation of a crop plant. An "increase in vigor" refers to an increase in growth or biomass accumulation of a crop plant relative to an untreated control crop plant. The term "crop yield" refers to the return, both in quantity and quality, of crop material obtained after harvesting a crop plant. An "increase in crop yield" refers to an increase in crop yield relative to an untreated control crop plant.

[0042] The term "biologically effective amount" refers to an amount of a biologically active compound (e.g., a compound of Formula 1) sufficient to produce the desired biological effect when applied to (i.e., contacted with) the invertebrate pest to be controlled or its environment, or the plant, the seed from which the plant grows, or the locus of the plant (e.g., the growing medium) to protect the plant from damage by the invertebrate pest or for other desired effects (e.g., increasing plant vigor).

[0043] In the above description, the term "alkyl", used alone or in compound words such as "alkylthio" or "haloalkyl", includes straight-chain or branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, or the different butyl, pentyl or hexyl isomers.

[0044] "Alkoxy" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy, pentoxy and hexoxy isomers. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.

[0045] The term "halogen", alone or in compound words such as "haloalkyl", or when used in descriptions such as "alkyl substituted by halogen", includes fluorine, chlorine, bromine or iodine. Furthermore, when used in compound words such as "haloalkyl", or when used in descriptions such as "alkyl substituted by halogen", the alkyl group may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" or "alkyl substituted by halogen" include F3C-, ClCH2-, C F3CH2- and C F3CCl2-.

[0046] As used herein, the chemical abbreviations S(O) and S(=O) denote a sulfinyl moiety. As used herein, the chemical abbreviations SO2, S(O)2, and S(=O)2 denote a sulfonyl moiety. As used herein, the chemical abbreviations C(O) and C(=O) denote a carbonyl moiety. As used herein, the chemical abbreviations CO2, C(O)O, and C(=O)O denote an oxycarbonyl moiety.

[0047] The dashed line in a structural fragment represents the point of attachment of the fragment to the rest of the molecule. For example, when the variable Q in Formula 1 is defined as Q-1, the dashed line in the Q-1 structure means that Q-1 is attached to the rest of the structure of Formula 1 at that position, as shown below. In addition, for compounds of Formula 1 in which Q is selected from pyridine, pyridazine, pyrimidine, and pyrazine, the pyridine, pyridazine, pyrimidine, and pyrazine are attached to the pyrazole ring of Formula 1 in such a way that the nitrogen ring atom of the pyridine, pyridazine, pyrimidine, or pyrazine is adjacent to the point of attachment.

[0048]

[0049] As described above, Q can be pyridine, pyridazine, pyrimidine, pyrazine or thiazole, wherein the pyridine, pyridazine, pyrimidine or pyrazine is optionally substituted with one or more substituents selected from the group of substituents defined in the Summary of the Invention. Non-limiting examples of variable Q are shown in Example 1.

[0050] Example 1

[0051]

[0052] The total number of carbon atoms in a substituent group is represented by "C i -C j " prefix indicates. For example, C1-C4 alkyl represents methyl, ethyl, and the various propyl and butyl isomers.

[0053] When a compound is substituted with a substituent having a subscript indicating that the number of said substituents may exceed 1, said substituents (when they exceed 1) are independently selected from the defined group of substituents. In addition, when a subscript indicates a range, for example (R) i-j , the number of substituents may be selected from integers between i and j (inclusive). When a group contains a substituent that may be hydrogen, it is recognized that when this substituent is hydrogen, this is equivalent to the group being unsubstituted. When one or more positions on a group are referred to as being "not substituted" or "unsubstituted", hydrogen atoms are attached to occupy any free valences.

[0054] When a substituent is a 5- or 6-membered nitrogen-containing heterocycle, unless otherwise specified, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom.

[0055] A variety of synthetic methods are known in the art to enable the preparation of aromatic and non-aromatic heterocycles and ring systems; for extensive reviews, see the eight-volume collection Comprehensive Heterocyclic Chemistry, edited by AR Katritzky and CW Rees, Pergamon Press, Oxford, 1984, and the twelve-volume collection Comprehensive Heterocyclic Chemistry II, edited by AR Katritzky, CW Rees, and EF V Scriven, Pergamon Press, Oxford, 1996.

[0056] The compounds of the present invention can exist as one or more stereoisomers. Stereoisomers are isomers that have the same composition but different arrangements of their atoms in space, and include enantiomers, diastereomers, cis-trans isomers (also referred to as geometric isomers) and atropisomers. Atropisomers are caused by limited rotation around a single bond, where the rotation barrier is high enough to allow separation of isomers. Those skilled in the art will appreciate that a stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to one or more other stereoisomers, or when separated from one or more other stereoisomers. In addition, those skilled in the art know how to separate, enrich and / or selectively prepare the stereoisomers. For a comprehensive discussion of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds [organic compound stereochemistry], John Wiley & Sons [John Wiley and Sons Publishers], 1994.

[0057] The compounds of the present disclosure may exist as a mixture of stereoisomers or as individual stereoisomers. For example, the two possible enantiomers of Formula 1 are depicted as Formula 1a and Formula 1a', including reference to the chiral carbon center identified with an asterisk (*).

[0058]

[0059] The molecules depicted herein follow standard conventions for depicting stereochemistry. To indicate stereoconfiguration, bonds extending out of the drawing plane toward the viewer are represented by solid wedges, with the wide end of the wedge attached to an atom extending out of the drawing plane toward the viewer. Bonds extending below the drawing plane and away from the viewer are represented by dashed wedges, with the wide end of the wedge attached to an atom further away from the viewer.

[0060] Due to the possible presence of chiral carbon atoms in Formula 1, the compounds of the present disclosure may exist as stereoisomers. Therefore, the present disclosure includes individual stereoisomers of compounds having Formula 1, as well as mixtures of stereoisomers of compounds having Formula 1.

[0061] Compounds of Formula 1 may contain additional chiral centers. The present disclosure includes racemic mixtures as well as enriched and substantially pure stereoconfigurations at these additional chiral centers.

[0062] The compounds of the present disclosure may exist as one or more conformers due to restricted rotation about any bond in Formula 1. The present disclosure includes mixtures of conformers. Additionally, the present disclosure includes compounds that are enriched in one conformer relative to other conformers.

[0063] The more biologically active enantiomer is believed to be of Formula 1a (the R-enantiomer of Formula 1).

[0064] The present disclosure includes racemic mixtures of equal amounts of an enantiomer having Formula 1a (the R-enantiomer of Formula 1) and an enantiomer having Formula 1a' (the S-enantiomer of Formula 1). Additionally, the present disclosure includes mixtures that are enriched in the enantiomer of Formula 1a compared to the racemic mixture of Formulas 1a and 1a'. The present disclosure also includes substantially pure enantiomers of Formula 1a.

[0065] Embodiments of the present disclosure include mixtures of stereoisomers of compounds having Formula 1a and compounds having Formula 1a', wherein the ratio of 1a to 1a' is at least 75:25 (50% enantiomeric excess).

[0066] Embodiments of the present disclosure include mixtures of stereoisomers of compounds having Formula 1a and compounds having Formula 1a', wherein the ratio of 1a to 1a' is at least 90:10 (80% enantiomeric excess of 1a).

[0067] Embodiments of the present disclosure include mixtures of stereoisomers of compounds having Formula 1a and compounds having Formula 1a', wherein the ratio of 1a to 1a' is at least 95:5 (90% enantiomeric excess of 1a).

[0068] Embodiments of the present disclosure include mixtures of stereoisomers of compounds having Formula 1a and compounds having Formula 1a', wherein the ratio of 1a to 1a' is at least 98:2 (96% enantiomeric excess of 1a).

[0069] Embodiments of the present disclosure include mixtures of stereoisomers of compounds having Formula 1a and compounds having Formula 1a', wherein the ratio of 1a to 1a' is at least 99:1 (98% enantiomeric excess of 1a).

[0070] Embodiments of the present disclosure include mixtures of stereoisomers of compounds having Formula 1a and compounds having Formula 1a', wherein the ratio of 1a to 1a' is substantially 100:0.

[0071] Embodiments of the present disclosure include compounds having Formula 1a.

[0072] The compound selected from Formula 1 typically exists in more than one form, and therefore Formula 1 includes all crystalline and non-crystalline forms of the compound represented by Formula 1. Non-crystalline forms include solid embodiments, such as waxes and gums, and liquid embodiments, such as solutions and melts. Crystalline forms include embodiments representing substantially single crystal types and embodiments representing mixtures of polymorphs (i.e., different crystalline types). The term "polymorph" refers to a specific crystalline form of a compound that can be crystallized in different crystalline forms, which have different molecular arrangements and / or conformations in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly bound or strongly bound to the crystal lattice. Polymorphs can differ in such chemical, physical and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate and bioavailability. It will be understood by those skilled in the art that the polymorphs of the compound represented by Formula 1 can exhibit beneficial effects (e.g., suitable for preparing useful formulations, improved biological properties) relative to another polymorph or mixture of polymorphs of the same compound represented by Formula 1. The preparation and separation of specific polymorphs of the compound represented by Formula 1 can be achieved by methods known to those skilled in the art, including, for example, crystallization using a selected solvent and temperature. The compounds of the present invention may exist as one or more crystalline polymorphs. The present invention includes both individual polymorphs and mixtures of polymorphs, including mixtures that are enriched in one polymorph relative to other polymorphs. For a comprehensive discussion of polymorphism, see R. Hilfiker, ed., Polymorphism In the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

[0073] Embodiments of the present invention as described in the Summary of the Invention include those described below. In the following embodiments, Formula 1 includes stereoisomers, N-oxides, and salts thereof.

[0074] Embodiment 1: A compound having formula 1, wherein X is O.

[0075] Embodiment 1a: A compound of Formula 1 wherein X is S.

[0076] Embodiment 2: A compound of Formula 1 as described in Embodiment 1 or Embodiment 1a, wherein A is CR 1 .

[0077] Embodiment 2a. A compound of Formula 1 as described in Embodiment 1 or Embodiment 1a wherein A is CH.

[0078] Embodiment 2b. A compound of Formula 1 as described in Embodiment 1 or Embodiment 1a wherein A is N.

[0079] Embodiment 3: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 1 are independently H, amino, cyano, halogen, nitro, C(S)NH2; or R 1 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is independently phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 are independently C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members independently selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace.

[0080] Embodiment 3a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 are independently amino, cyano, halogen, nitro, C(S)NH2; or R 1 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is independently phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 are independently C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members independently selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace.

[0081] Embodiment 3b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 are independently cyano, halogen, nitro, C(S)NH2; or R 1 is independently C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, or C3-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 are independently C3-C9-trialkylsilyl, C(O)C1-C6, CR 7 (=NO)R 7 、C(O)OR7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members independently selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 , or S(O) p R 7 replace.

[0082] Embodiment 3c: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is a halogen, or R 1 is C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C3-C6 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally substituted by one or more R 6 Replacement; or R 1 It is C3-C9-trialkylsilyl, C(O)C1-C6, CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 , or C(O)OC1-C6 substituted.

[0083] Embodiment 3d: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is a halogen, or R 1 is C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or, wherein the alkyl, alkenyl or alkynyl groups are each optionally substituted by one or more R 6 Replacement; or R 1 C(O)C1-C6, CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7, OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 , or OS(O)2R 9 .

[0084] Embodiment 3e: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is a halogen, or R 1 is C1-C3 alkyl, C2-C4 alkenyl or C2-C4 alkynyl, wherein the alkyl, alkenyl or alkynyl groups are each optionally substituted by one or more R 6 Replacement; or R 1 It is C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 , or OS(O)2R 9 .

[0085] Embodiment 3f: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is a halogen, or R 1 is C1-C3 alkyl or C2-C4 alkenyl, wherein the alkyl or alkenyl groups are each optionally substituted by one or more R 6 Replacement; or R1 It's CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 , or OS(O)2R 9 .

[0086] Embodiment 3g: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is a halogen, or R 1 is a C1-C3 alkyl group, wherein each alkyl group is optionally replaced by one or more R 6 Replacement; or R 1 is OR 7 , SCF3 or OS(O)2R 9 .

[0087] Embodiment 3h: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is Cl, F, or Br, or R 1 is a C1-C3 alkyl group, wherein each alkyl group is optionally replaced by one or more R 6 Replacement; or R 1 is OR 7 , SCF3 or OS(O)2R 9 .

[0088] Embodiment 3i: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is Cl, F, or Br, or R 1 is a C1-C3 alkyl group, wherein each alkyl group is optionally replaced by one or more R 6 Replacement; or R1 OMe, SCF3, or OS(O)2R 9

[0089] Embodiment 3j: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is Cl, F, or Br, or R 1 is optionally replaced by one or more R 6 Substituted Me; or R 1 OMe, SCF3, or OS(O)2R 9 .

[0090] Embodiment 3k: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 is Cl, F, or Br, or R 1 is a C1-C3 alkyl group, wherein each alkyl group is optionally replaced by one or more R 6 replace;

[0091] Embodiment 31: A compound of formula 1 as described in any of the preceding embodiments, wherein R 1 It is Cl, or R 1 is optionally replaced by one or more R 6 Replaced Me.

[0092] Embodiment 3m: A compound of formula 1 according to any of the preceding embodiments, wherein n is 2, and each R 1 is Cl, or each R 1 is CF3, or one R1 is Cl and one R 1 It's CF3.

[0093] Embodiment 3n: A compound of Formula 1 according to any of the preceding embodiments, wherein n is 2, and each R 1 Located at the 3 and 5 positions of the benzene ring.

[0094] Embodiment 4: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0095] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0096] Embodiment 4a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 2 is hydrogen, C1-C4 alkyl, or C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 replace;

[0097] Embodiment 4b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 2 is hydrogen, or C1-C4 alkyl, wherein each alkyl is optionally substituted by one R 6 Replacement; or R 2 It is C(O)R 7 or C(O)OR 7 .

[0098] Embodiment 4c: A compound of formula 1 as described in any of the preceding embodiments, wherein R 2 is hydrogen, or C1-C4 alkyl, wherein each alkyl is optionally substituted by one R 6 Replacement; or R 2 It is C(O)R 7 .

[0099] Embodiment 4d: A compound of formula 1 as described in any of the preceding embodiments, wherein R 2 is H, or C1-C4 alkyl, wherein each alkyl is optionally substituted by one R 6 replace.

[0100] Embodiment 4e: A compound of formula 1 as described in any of the preceding embodiments, wherein R 2 is H, or C1-C3 alkyl, wherein each alkyl is optionally substituted by one R 6 replace.

[0101] Embodiment 4f: A compound of formula 1 as described in any of the preceding embodiments, wherein R 2 It is H, or C1-C3 alkyl, or CH2c-Pr.

[0102] Embodiment 4f: A compound of formula 1 as described in any of the preceding embodiments, wherein R 2 It is H or Me.

[0103] Embodiment 5: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 3 It is a C1-C3 alkyl group or a C1-C3 haloalkyl group.

[0104] Embodiment 5a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 3 It is a C1-C3 alkyl group.

[0105] Embodiment 5b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 3 It's me.

[0106] Embodiment 6: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 4 It is C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11SO2NR 7 R 8 .

[0107] Embodiment 6a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted by one or more R 6 Replace, or R 4 It is NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 .

[0108] Embodiment 6b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted by one or more R 6 Replace, or R 4 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 .

[0109] Embodiment 6b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted by one or more R 6 Replace, or R 4 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 , or S(O) p R 9 .

[0110] Embodiment 6c: A compound of formula 1 as described in any of the preceding embodiments, wherein R4 is hydrogen, cyano, nitro, Cl, or C1-C3 alkyl, wherein the alkyl is optionally substituted by one or more R 6 Replace, or R 4 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 , or S(O) p R 9 .

[0111] Embodiment 6d: A compound of formula 1 as described in any of the preceding embodiments, wherein R 4 It is cyano, nitro, or SO2Me.

[0112] Embodiment 7: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 5 It is C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0113] Embodiment 7a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, halogen, nitro, C1-C3-alkyl or C3-C6-cycloalkyl, wherein alkyl or cycloalkyl are each optionally substituted by one or more R 6 Replacement; or R 5 is OR 7 NR 7R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 , or SO2NR 7 R 8 .

[0114] Embodiment 7b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, cyano, halogen, nitro, or C1-C3-alkyl or C3-C6-cycloalkyl, wherein each alkyl group is optionally substituted by one or more R 6 Replacement; or R 5 is OR 7 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 , or SO2NR 7 R 8 .

[0115] Embodiment 7c: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, cyano, halogen, nitro, or C1-C3-alkyl, wherein alkyl or cycloalkyl are each optionally substituted by one or more R 6 Replacement; or R 5 is OR 7 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 , or SO2NR 7 R 8 .

[0116] Embodiment 7d: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, cyano, halogen, nitro, or C1-C3-alkyl; or R 5 is OR 7 NR 7 R 8 NR 8 C(O)R 7 NR8 C(O)OR 7 、S(O) p R 7 , or SO2NR 7 R 8 .

[0117] Embodiment 7e: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, halogen, or R 5 is OR 7 NR 7 R 8 NR 8 C(O)R 7 , or NR 8 C(O)OR 7 .

[0118] Embodiment 7f: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, cyano, Br, Cl, F, nitro, or C1-C3-alkyl; or R 5 is OR 7 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 , or SO2NR 7 R 8 .

[0119] Embodiment 7g: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, cyano, Br, Cl, F, nitro, or C1-C3-alkyl; or R 5 is OR 7 NR 7 R 8 NR 8 C(O)R 7 , or NR 8 C(O)OR 7 .

[0120] Embodiment 7h: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, cyano, Br, Cl, F, nitro, or Me; or R 5 is OR 7 NR 7 R 8 NR 8C(O)R 7 , or NR 8 C(O)OR 7 .

[0121] Embodiment 7i: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, cyano, Br, Cl, F, nitro, or Me; or R 5 is OMe, NH2, NHMe, SMe, N(Me)2, or NHC(O)Me.

[0122] Embodiment 7j: A compound of formula 1 as described in any of the preceding embodiments, wherein R 5 is hydrogen, cyano, Cl, nitro, or Me; or R 5 is OMe, NH2, NHMe, SMe, N(Me)2, or NHC(O)Me.

[0123] Embodiment 8: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or S(=NR)O p R 7 ;

[0124] Embodiment 8a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 6is halogen, cyano, nitro, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 , SF 5、 S(O) p R 9 , or SO2NR 7 R 8 .

[0125] Embodiment 8b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 6 is halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 , or C(O)NR 7 R 8 .

[0126] Embodiment 8c: A compound of formula 1 as described in any of the preceding embodiments, wherein R 6 It is halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or C3-C7 cycloalkyl.

[0127] Embodiment 8d: A compound of formula 1 as described in any of the preceding embodiments, wherein R 6 is halogen, cyano, C1-C3 alkyl, or C1-C3 haloalkyl.

[0128] Embodiment 8e: A compound of formula 1 as described in any of the preceding embodiments, wherein R 6 is F, cyano, C1-C3 alkyl, or C1-C3 haloalkyl.

[0129] Embodiment 9: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0130] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace.

[0131] Embodiment 9a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 7 is hydrogen, C1-C3 alkyl, C2-C3 alkenyl, C3-C4 alkynyl, C3-C6 cycloalkyl, or C5-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl are each optionally replaced by one or more R 12 Replace; or

[0132] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace.

[0133] Embodiment 10: A compound of formula 1 as described in any of the preceding embodiments, wherein R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 Replace; or

[0134] When R 7 and R 8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 .

[0135] Embodiment 10a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 8is hydrogen, or C1-C3, C1-C3 alkoxy, C3-C4 alkenyl, C4-C5 alkenyloxy, C3-C5 alkynyl, or C4-C5 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace.

[0136] Embodiment 11: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0137] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0138] Embodiment 11a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 9 is C1-C3 alkyl, C3-C5 alkenyl, C3-C5 alkynyl, or C4-C6 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is each optionally substituted by one or more R 6 Replace; or

[0139] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0140] Embodiment 11b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 9 is C1-C3 alkyl, C3-C5 alkenyl, C3-C5 alkynyl, or C4-C6 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl are each optionally substituted by one or more R 6 replace.

[0141] Embodiment 12: A compound of formula 1 as described in any of the preceding embodiments, wherein R 10 It is H, C1-C6 alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, or C1-C3-alkoxy-C1-C3-alkyl.

[0142] Embodiment 12a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 10 It is H, C1-C6 alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl.

[0143] Embodiment 12b: A compound of formula 1 as described in any of the preceding embodiments, wherein R 10 It is H, C1-C6 alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl.

[0144] Embodiment 12c: A compound of formula 1 as described in any of the preceding embodiments, wherein R 10 It is H, C1-C6 alkyl, C1-C6-haloalkyl.

[0145] Embodiment 13: A compound of formula 1 as described in any of the preceding embodiments, wherein R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 .

[0146] Embodiment 13a: A compound of formula 1 as described in any of the preceding embodiments, wherein R 11 is hydrogen, C1-C3 alkyl, C3-C5 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 .

[0147] Embodiment 14: A compound of formula 1 as described in any one of the preceding embodiments, wherein R 12 It is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, wherein alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is each optionally substituted by halogen or cyano.

[0148] Embodiment 14a: A compound of formula 1 according to any one of the preceding embodiments, wherein R 12 It is halogen, hydroxyl, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, wherein the alkyl, alkoxy, alkenyl and alkynyl are each optionally substituted with halogen or cyano.

[0149] Embodiment 14b: A compound of formula 1 according to any one of the preceding embodiments, wherein R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, wherein each alkyl group is optionally substituted by halogen or cyano.

[0150] Embodiment 15: A compound of Formula 1 as described in any of the preceding embodiments, wherein Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8, or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0151] Embodiment 15a: A compound of Formula 1 as described in any of the preceding embodiments, wherein Q is pyridine, pyridazine, pyrimidine, or pyrazine, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups selected from amino, cyano, halogen, nitro, C1-C3 alkyl, C5-C7 cycloalkylalkyl, C3-C5 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or cycloalkylalkyl, wherein each of alkyl, alkoxy, cycloalkyloxy, alkoxyalkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0152] Embodiment 15b: A compound of Formula 1 as described in any of the preceding embodiments, wherein Q is pyridine, pyridazine, or pyrimidine, wherein the pyridine, pyridazine, or pyrimidine is optionally substituted with one to three groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein each of the alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0153] Embodiment 15c. A compound of Formula 1 as described in any of the preceding embodiments, wherein Q is selected from Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, and Q-26.

[0154] Embodiment 15d. A compound of Formula 1 as described in any of the preceding embodiments, wherein Q is selected from Q-1, Q-2, Q-6, Q-7, Q-11, Q-13, Q-14, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, and Q-25.

[0155] Embodiment 15e. A compound of Formula 1 as described in any of the preceding embodiments, wherein Q is selected from Q-1, Q-2, Q-13, Q-14, Q-19, and Q-24.

[0156] Embodiment 15f. A compound of Formula 1 as described in any one of the preceding embodiments, wherein Q is selected from Q-1, and Q-2.

[0157] Embodiment 15g. A compound of Formula 1 as described in any of the preceding embodiments, wherein Q is Q-2.

[0158] Embodiment 16: A compound of Formula 1 according to any of the preceding embodiments, wherein n is 1 or 2.

[0159] Embodiment 16a: A compound of Formula 1 according to any of the preceding embodiments, wherein n is 2.

[0160] Embodiment 17: A compound of Formula 1 according to any of the preceding embodiments, wherein p is 0 or 1.

[0161] Embodiment 17a. A compound of Formula 1 according to any of the preceding embodiments, wherein p is 0.

[0162] The embodiments of the present invention (including Examples 1-17a above and any other embodiments described herein) can be combined in any manner, and the descriptions of the variables in the embodiments relate not only to compounds having Formula 1, but also to starting compounds and intermediate compounds that can be used to prepare compounds having Formula 1. In addition, the embodiments of the present disclosure (including Examples 1-17a above and any other embodiments described herein) and any combination thereof relate to the compositions and methods of the present invention.

[0163] In some embodiments, when R 1 When it is not H, R 1 Not positioned adjacent to C(X).

[0164] In some embodiments, R 4 and R 5 Both are not hydrogen.

[0165] In some embodiments, when R 1 When it is not H, R 1 is not located adjacent to C(X), and

[0166] R 4 and R 5 Both are not hydrogen.

[0167] Example X. A method for controlling and combating invertebrate pests, the method comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound having Formula 1.

[0168] Embodiment X1. The method of claim X, wherein the environment is soil or plant foliage.

[0169] The embodiments of the present disclosure (including the above-mentioned Embodiments 1-X1 and any other embodiments described herein) can be combined in any manner, and the descriptions of the variables in the embodiments relate not only to compounds having Formula 1, but also to starting compounds and intermediate compounds that can be used to prepare compounds having Formula 1. In addition, the embodiments of the present disclosure (including the above-mentioned Embodiments 1-X1 and any other embodiments described herein) and any combination thereof relate to the compositions and methods of the present disclosure.

[0170] The combination of Examples 1-17a is shown below:

[0171] Embodiment A1. A compound having Formula 1, wherein

[0172] X is O;

[0173] n is 1, 2, or 3;

[0174] p is 0, 1, or 2;

[0175] A is CH;

[0176] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O)p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0177] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6 substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0178] R 2 It is C(O)R 7 、C(O)OR 7 NR7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0179] R 3 is C1-C3 alkyl or C1-C3 haloalkyl;

[0180] R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ;

[0181] R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0182] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 ,NR8C(O)R7,NR8C(O)OR7,OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or S(=NR)O p R 7 ;

[0183] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 12 Replace; or

[0184] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace;

[0185] R 8is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0186] When R7 and R8 are on N, R7 and R8 may form a 3 to 7 carbon ring, which optionally contains oxygen, S(O)p or NR 7 ;

[0187] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0188] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0189] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0190] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0191] R 12 It is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, wherein alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is each optionally substituted by halogen or cyano.

[0192] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0193] Embodiment A2. The compound of Formula 1 according to Embodiment A1, wherein

[0194] X is O;

[0195] n is 1, 2, or 3;

[0196] p is 0, 1, or 2;

[0197] A is CH;

[0198] R 1 is a halogen, or R 1 is C1-C3 alkyl, or C2-C4 alkenyl, wherein the alkyl, or alkenyl are each optionally substituted with one or more R 6 Replacement; or R 1 It's CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 , or OS(O)2R 9 .

[0199] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0200] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0201] R 3 is a C1-C3 alkyl group;

[0202] R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ;

[0203] R 5is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0204] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 ,NR8C(O)R7,NR8C(O)OR7,OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or S(=NR)O p R 7 ;

[0205] R 7is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 12 Replace; or

[0206] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace;

[0207] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0208] When R 7 and R 8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 ;

[0209] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0210] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0211] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0212] R 11is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0213] R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C4-C8 cycloalkylalkyl, wherein alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted with halogen or cyano;

[0214] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8, or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0215] Embodiment A3. The compound of Formula 1 as described in Embodiment A1, wherein

[0216] X is O;

[0217] n is 1, 2, or 3;

[0218] p is 0, 1, or 2;

[0219] A is CH;

[0220] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0221] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0222] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0223] R 3 is a C1-C3 alkyl group;

[0224] R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ;

[0225] R 5is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally replaced by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0226] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 ,NR8C(O)R7,NR8C(O)OR7,OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 ;

[0227] R 7is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 12 Replace; or

[0228] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace;

[0229] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0230] When R 7 and R 8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 ;

[0231] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0232] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0233] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0234] R 11is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0235] R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, wherein each alkyl group is optionally substituted by halogen or cyano.

[0236] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8, or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0237] Embodiment A4. The compound of Formula 1 according to Embodiment A1, wherein

[0238] X is O;

[0239] n is 1, 2, or 3;

[0240] p is 0, 1, or 2;

[0241] A is CH;

[0242] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0243] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0244] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0245] R 3 is a C1-C3 alkyl group;

[0246] R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 replace;

[0247] R 5 is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally replaced by one or more R 6 Replacement; or R 5 It is C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 , or SO2NR7 R 8 ;

[0248] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 ;

[0249] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0250] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0251] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0252] When R 7 and R8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 ;

[0253] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0254] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0255] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0256] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0257] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0258] Embodiment A5. The compound of Formula 1 according to Embodiment A1, wherein

[0259] X is O;

[0260] n is 1, 2, or 3;

[0261] p is 0, 1, or 2;

[0262] A is CH;

[0263] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8replace;

[0264] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6 substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0265] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0266] R 3 is a C1-C3 alkyl group;

[0267] R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, wherein each alkyl group is optionally replaced by one or more R 6 replace;

[0268] R 5 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 5 It is NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9, or SO2NR 7 R 8 ;

[0269] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0270] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0271] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0272] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0273] When R 7and R 8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 ;

[0274] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0275] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0276] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0277] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0278] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0279] Embodiment A6. The compound of Formula 1 according to Embodiment A1, wherein

[0280] X is O;

[0281] n is 1, 2, or 3;

[0282] p is 0, 1, or 2;

[0283] A is CH;

[0284] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0285] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is optionally replaced by one or more R 6 Substituted C1-C6 alkyl

[0286] R 3 It's Me;

[0287] R 4 is hydrogen, cyano, halogen, nitro, C1-C3 alkyl, wherein each alkyl group is optionally substituted by one or more R 6 replace;

[0288] R 5 is hydrogen, cyano, halogen, nitro; or R 5 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0289] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 ;

[0290] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0291] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0292] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0293] When R 7 and R 8 When on N, R 7 and R8 can form a 3 to 7 carbon ring, which optionally contains oxygen, S(O)p or NR 7 ;

[0294] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0295] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0296] R 10is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0297] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0298] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8, or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0299] Embodiment A7. The compound of Formula 1 according to Embodiment A1, wherein

[0300] X is O;

[0301] n is 1 or 2;

[0302] p is 0, 1, or 2;

[0303] A is CH;

[0304] R 1 is a halogen; or R 1 is a C1-C6 alkyl group, wherein each alkyl group is optionally replaced by one or more R 6 replace;

[0305] R 2 It is hydrogen or C1-C6 alkyl.

[0306] R 3 It's Me;

[0307] R 4 is cyano or nitro;

[0308] R 5 is hydrogen, cyano, halogen, nitro; or R 5 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 、S(O) p R9 , or SO2NR 7 R 8 ;

[0309] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 ;

[0310] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0311] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0312] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0313] When R7 and R 8 When on N, R 7 and R8 can form a 3 to 7 carbon ring, which optionally contains oxygen, S(O)p or NR 7 ;

[0314] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0315] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0316] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0317] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ; and Q

[0318] Selected from Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, Q-9, Q-10, Q-11, Q-12, Q-13, Q-14 , Q-15, Q-16, Q-17, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, Q-25, and Q-26.

[0319] Embodiment A8. The compound of Formula 1 according to Embodiment A1, wherein

[0320] A is CH;

[0321] N is 1 or 2;

[0322] R 1 Is Cl, or F, or R1 is optionally replaced by one or more R 6 Replaced Me.

[0323] R 2 is hydrogen, CH2c-Pr, or Me;

[0324] R 3 It's Me;

[0325] R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted by one or more R 6 Replace, or R 4 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 , or S(O) p R 9 ;

[0326] R 5 is hydrogen, cyano, Br, Cl, F, nitro, or C1-C3-alkyl; or R 5 is OR 7 NR 7 R 8 NR 8 C(O)R 7 , or NR 8 C(O)OR 7 ,and

[0327] Q is Q-1, Q-2, Q-6, Q-7, Q-11, Q-13, Q-14, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, or Q-25.

[0328] Embodiment A9. The compound of Formula 1 according to Embodiment 1, wherein

[0329] X is O;

[0330] A is CH;

[0331] n is 2;

[0332] R 1 Is Cl, or F, or R 1 is optionally replaced by one or more R 6 Replaced Me.

[0333] R 2 is hydrogen, CH2c-Pr, or Me;

[0334] R 3 It's Me;

[0335] R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted by one or more R 6 Replace, or R 4 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 , or S(O) p R 9 ;

[0336] R 5 is hydrogen, cyano, Br, Cl, F, nitro, or C1-C3-alkyl; or R 5 is OR 7 NR 7 R 8 NR 8 C(O)R 7 , or NR 8 C(O)OR 7 ,and

[0337] Q is Q-1, Q-2, Q, Q-13, Q-14, Q-19, or Q-24.

[0338] Embodiment A10. A compound of Formula 1, wherein

[0339] X is O;

[0340] n is 1, 2, or 3;

[0341] p is 0, 1, or 2;

[0342] A is CR 1 ;

[0343] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0344] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2is a C1-C6 alkyl group, which is optionally replaced by one or more R 6 substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0345] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0346] R 3 is C1-C3 alkyl or C1-C3 haloalkyl;

[0347] R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ;

[0348] R 5is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0349] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 ,NR8C(O)R7,NR8C(O)OR7,OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or S(=NR)O p R 7 ;

[0350] R 7is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 12 Replace; or

[0351] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace;

[0352] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0353] When R7 and R8 are on N, R7 and R8 may form a 3 to 7 carbon ring, which optionally contains oxygen, S(O)p or NR 7 ;

[0354] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0355] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0356] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0357] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R7 、C(O)OR 7 , or S(O) p R 7 ;

[0358] R 12 It is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, wherein alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl is each optionally substituted by halogen or cyano.

[0359] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8, or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0360] Embodiment A11. The compound of Formula 1 according to Embodiment A10, wherein

[0361] X is O;

[0362] n is 1, 2, or 3;

[0363] p is 0, 1, or 2;

[0364] A is CR 1 ;

[0365] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0366] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0367] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0368] R 3 is a C1-C3 alkyl group;

[0369] R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ;

[0370] R 5is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0371] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 ,NR8C(O)R7,NR8C(O)OR7,OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or S(=NR)O p R 7 ;

[0372] R 7is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 12 Replace; or

[0373] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace;

[0374] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0375] When R 7 and R 8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 ;

[0376] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0377] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0378] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0379] R 11is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0380] R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C4-C8 cycloalkylalkyl, wherein alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted with halogen or cyano;

[0381] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8, or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0382] Embodiment A12. The compound of Formula 1 according to Embodiment A10, wherein

[0383] X is O;

[0384] n is 1, 2, or 3;

[0385] p is 0, 1, or 2;

[0386] A is CR 1 ;

[0387] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0388] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0389] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0390] R 3 is a C1-C3 alkyl group;

[0391] R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ;

[0392] R 5is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally replaced by one or more R 6 Substitution; C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0393] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 ,NR8C(O)R7,NR8C(O)OR7,OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 ;

[0394] R 7is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 12 Replace; or

[0395] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace;

[0396] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0397] When R7 and R8 are on N, R7 and R8 may form a 3 to 7 carbon ring, which optionally contains oxygen, S(O)p or NR 7 ;

[0398] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0399] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0400] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0401] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R7 、C(O)OR 7 , or S(O) p R 7 ;

[0402] R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, wherein each alkyl group is optionally substituted by halogen or cyano.

[0403] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8, or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0404] Embodiment A13. The compound of Formula 1 according to Embodiment A10, wherein

[0405] X is O;

[0406] n is 1, 2, or 3;

[0407] p is 0, 1, or 2;

[0408] A is CR 1 ;

[0409] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0410] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0411] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0412] R 3 is a C1-C3 alkyl group;

[0413] R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 replace;

[0414] R 5 is hydrogen, cyano, halogen, nitro, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally replaced by one or more R 6 Replacement; or R 5 It is C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 , or SO2NR7 R 8 ;

[0415] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 ;

[0416] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0417] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0418] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0419] When R 7 and R8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 ;

[0420] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0421] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0422] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0423] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0424] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0425] Embodiment A14. The compound of Formula 1 according to Embodiment A10, wherein

[0426] X is O;

[0427] n is 1, 2, or 3;

[0428] p is 0, 1, or 2;

[0429] A is CR 1 ;

[0430] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0431] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is a C1-C6 alkyl group, which is optionally replaced by one or more R 6 substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or

[0432] R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ;

[0433] R 3 is a C1-C3 alkyl group;

[0434] R 4 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, wherein each alkyl group is optionally replaced by one or more R 6 replace;

[0435] R 5 is hydrogen, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 5 It is NR 7 R 8 NR 8 C(O)R 7 NR8 C(O)OR 7 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0436] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0437] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0438] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0439] R 8is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0440] When R 7 and R 8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, optionally containing oxygen, S(O)p or NR 7 ;

[0441] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0442] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0443] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0444] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0445] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0446] Embodiment A15. The compound of Formula 1 according to Embodiment A10, wherein

[0447] X is O;

[0448] n is 1, 2, or 3;

[0449] p is 0, 1, or 2;

[0450] A is CR 1 ;

[0451] R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replacement; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 、SF5、SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR11 )O p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace;

[0452] R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replacement; or R 2 is optionally replaced by one or more R 6 Substituted C1-C6 alkyl

[0453] R 3 It's Me;

[0454] R 4 is hydrogen, cyano, halogen, nitro, C1-C3 alkyl, wherein each alkyl group is optionally substituted by one or more R 6 replace;

[0455] R 5 is hydrogen, cyano, halogen, nitro; or R 5 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0456] R 6Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 ;

[0457] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0458] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0459] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0460] When R 7 and R 8 When on N, R 7 and R8 can form a 3 to 7 carbon ring, which optionally contains oxygen, S(O)p or NR 7;

[0461] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0462] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0463] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0464] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ;

[0465] Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, with C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

[0466] Embodiment A16. The compound of Formula 1 according to Embodiment A10, wherein

[0467] X is O;

[0468] n is 1 or 2;

[0469] p is 0, 1, or 2;

[0470] A is CR 1 ;

[0471] R 1 is a halogen; or R 1 is a C1-C6 alkyl group, wherein each alkyl group is optionally replaced by one or more R 6 replace;

[0472] R 2 It is hydrogen or C1-C6 alkyl.

[0473] R 3 It's Me;

[0474] R4 is cyano or nitro;

[0475] R 5 is hydrogen, cyano, halogen, nitro; or R 5 It is NR 7 R 8 NR 8 C(O)R 7 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ;

[0476] R 6 Halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 ;

[0477] R 7 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or

[0478] R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R6 replace;

[0479] R 8 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally replaced by one or more R 6 replace;

[0480] When R 7 and R 8 When on N, R 7 and R8 can form a 3 to 7 carbon ring, which optionally contains oxygen, S(O)p or NR 7 ;

[0481] R 9 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl group is optionally replaced by one or more R 6 Replace; or

[0482] R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace;

[0483] R 10 is H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl;

[0484] R 11 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 .

[0485] Embodiment A17. The compound of Formula 1 according to Embodiment A10, wherein

[0486] X is O or S;

[0487] A is N or CR 1 ;

[0488] R 1 is Cl, F, or Br, or R 1 is optionally replaced by one or more R 6 Substituted Me; or R 1 OMe, SF3, or OS(O)2R 9 .

[0489] R 2 is hydrogen, C1-C4 alkyl, or C4-C6 cycloalkylalkyl, wherein alkyl or cycloalkylalkyl are each optionally substituted by one R 6 Replace; or

[0490] R 2 It is C(O)R 7 or C(O)OR 7 ;

[0491] R 3 is Me; and

[0492] R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted by one or more R 6 replace.

[0493] Embodiment A18. The compound of Formula 1 according to Embodiment A10, wherein

[0494] X is O or S;

[0495] A is N or CR 1 ;

[0496] R 1 is Cl, F, or Br, or R 1 is optionally replaced by one or more R 6 Substituted Me; or R 1 OMe, SF3, or OS(O)2R 9 .

[0497] R 2 is hydrogen, C1-C4 alkyl, or C4-C6 cycloalkylalkyl, wherein alkyl or cycloalkylalkyl are each optionally substituted by one R 6 Replace; or

[0498] R 2 It is C(O)R 7 or C(O)OR 7 ;

[0499] R 3 It's Me;

[0500] R 4is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted by one or more R 6 replace; and

[0501] Q is Q-1, Q-2, Q-6, Q-7, Q-11, Q-13, Q-14, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, or Q-25.

[0502] Specific embodiments include compounds having Formula 1 selected from the group consisting of compounds as described in Table A.

[0503] Table A

[0504]

[0505]

[0506]

[0507] 1 Cas name

[0508] 2 Chemical names automatically generated using ChemDraw Professional, version 17.0.

[0509] Embodiment Y1. A composition comprising a compound of formula 1 as described in any of the preceding embodiments and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising at least one additional biologically active compound or agent. Embodiment Y2. A composition as described in embodiment Y1, wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acequinoxaline, acetamiprid, fluazifop, bicyclam, sulfanilamide, amitraz, avermectin, azadirachtin, azophos, benzylpyridin, benfuracarb, sulfanilamide, bifenthrin, bifenazate, bistrifluan, borate, bromantraniliprole, thiamethoxam, carbaryl, carbofuran, cartap, chlorfenapyr, chlorfenapyr, chlorpyrifos, methyl chlorpyrifos, cyclohexanil, chlorpyrifos ... Hydrazide, clofenac, clothianidin, cyantraniliprole, cyclic bromofenac, triflupyramide, cypermethrin, cycloheximide, ethoxyfenapyr, cyfluthrin, beta-cyfluthrin, cyfluthrin, beta-cyfluthrin, cyfluthrin, beta-cyfluthrin, beta-cyfluthrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, cyprodinil, cyromazine, deltamethrin, diafenthiuron, diazinon, dichlorantraniliprole, dieldrin, flumethoxam, diflubenzuron, tetrafluthrin, dimethoate, dimethoate, dinotefuran, fenfluramide, emamectin, endosulfan, cypermethrin, ethiprole, ether Pyrethroids, etoxazole, quinazaquin, fenbutatin, fenitrothion, bithiazole, fenthiocarb, fenoxycarb, fenpyroximate, cypermethrin, cypermethrin, flufenoxam, flumetol, flonicamid, pyrimidifen, trifluanid, flubendiamide, fluchlorfenapyr, flucyvalerate, flufenoxam, flufenoxuron, flufenoxam, fluensulfone, fluhexafon, flupyram, fluflufenamid, flupyrad, flupyrad, flupyronil, flupyrad, fluvalinate, fluoxafonamide, flufenoxam ... , methoprene, imidacloprid, indoxamide (N-(1-methylcyclopropyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide), indoxacarb, insecticidal soap, isopropylamine, isoxathiapiprolin, κ-tefluthrin, methoprene, lufenuron, malathion, chlorfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, methoxyfluthrin, monocrotophos, monofluthrin, tolfenpyrad, nicotine, N-[1,1-dimethyl-2-(methylthio)ethyl]-7-fluoro-2-(3-pyridyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridyl)-2H-indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide, N-[1-(difluoromethyl)cyclopropyl]-2-(3- (pyridyl)-2H-indazole-4-carboxamide, nitenpyram, nithiazine, fluazifop, noviflumuron, oxamyl, oxazolidinone, parathion, methyl parathion, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargyl, profenthrin, flubutamide, pymetrozine, pyrimidine, pyrethrins (pyrethrum), Pyridaben, pyridalyl, pyrimethamine, pyraclostrobin, pyrimethamine, pyraclostrobin, pyriproxyfen, rotenone, ryanodine, flutoxin, dispirochlor, ethyl spinosad, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfopropanone, sulfoxaflor, tebufenozide, tebufenpyrad, flubendiamide, tefluthrin, κ-tefluthrin, terbufos, tetrachlorvinphos, cypermethrin, tetrafluthrin, tetrazolam, thiamethoxam, thiamethoxam , thiodicarb, thiosultap, dimethoate, thiobencarb, thiamethoxam, tolfenpyrad, tralomethrin, triazolam, triflumuron, triflumuron, chlorpyrifos, Bacillus sphaericus, Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi, plant essences including synthetic extracts and unrefined oils, RNA interference-mediated target inhibitors.

[0510] Embodiment Y3. The composition of embodiment Y2, wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acetamiprid, flumethrin, biprofenapyr, amitraz, avermectin, azadirachtin, benfuracarb, sulfamethoxam, bifenthrin, buprofezin, carbaryl, cartap, chlorfenapyr, chlorpyrifos, clothianidin, cyanamide, cypermethrin, cyproconazole, chlorpyrifos, chlorfenapyr ... Ester, cyfluthrin, high-efficiency cyfluthrin, cyfluthrin, fine high-efficiency cyfluthrin, high-efficiency cyfluthrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, benzylpezil, emamectin, endosulfan, cypermethrin, ethomethrin, etoxazole, fenitrothion, fenthiocarb, fenoxycarb, cypermethrin, fipronil, flumetoquinone, flonicamid, flubendiamide, Flufenoxuron, flufenoxanil, diflunisal, butyronitrile (flupiprole), flupyralidone, fluvalinate, flumethrin, thiamethoxam, tefluthrin, hexaflumuron, hydrazone, imidacloprid, indoxacarb, lufenuron, chlorfluthrin, metaflumizone, methiocarb, methomyl, methoprene, methoxyfenozide, metofluthrin, monofluthrin, nitenpyram, nithiazine, flupyuron, oxamyl, pyrimethamine, pymetrozine, Pyrethrins, pyridabenz, pyridalyl, pyrimidine, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetrafluthrin, thiacloprid, thiomethoxam, thiodicarb, dimehypo, tralomethrin, triazolam, triflumuron, Bacillus thuringiensis delta-endotoxin, all strains of Bacillus thuringiensis and all strains of nuclear polyhedrosis viruses.

[0511] Embodiment Y4. The composition of any one of embodiments Y1-Y3, further comprising a liquid fertilizer.

[0512] Embodiment Y5. The composition of embodiment Y4, wherein the liquid fertilizer is water-based.

[0513] Embodiment Y6. A soil soak formulation comprising the composition of any one of embodiments Y1 to Y3. Embodiment Y7. A spray composition comprising the composition of any one of embodiments Y1 to Y3 and a propellant.

[0514] Embodiment Y8. A bait composition comprising the composition of any one of embodiments Y1-Y3, one or more food materials, an optional attractant, and an optional wetting agent.

[0515] Example Y9. A trapping device for controlling and combating invertebrate pests, the trapping device comprising: a bait composition as described in Example Y8 and a shell adapted to accommodate the bait composition, wherein the shell has at least one opening, the size of the opening is set to allow invertebrate pests to pass through the opening, so that the invertebrate pests can approach the bait composition from a position outside the shell, and wherein the shell is further adapted to be placed in or near a location where the invertebrate pests may or are known to be active.

[0516] Embodiment Y10. A composition comprising the composition of any one of embodiments Y1-Y3, wherein the composition is a solid composition selected from dusts, powders, granules, pellets, granules, lozenges, tablets, and filled films.

[0517] Embodiment Y11. The composition of embodiment Y10, wherein the composition is water dispersible or water soluble.

[0518] Embodiment Y12. A liquid or dry formulation comprising the composition of any one of embodiments Y1-Y3 for use in a drip irrigation system, in-furrow during planting, a handheld sprayer, a backpack sprayer, a boom sprayer, a ground sprayer, aerial application, an unmanned aerial vehicle, or seed treatment.

[0519] Embodiment Y13. The liquid or dry formulation of embodiment Y12, wherein the formulation is sprayed at ultra-low volume.

[0520] Notably, the compounds of the present invention are characterized by favorable metabolic and / or soil residue patterns and exhibit activity against a broad spectrum of agronomic and non-agronomic invertebrate pests.

[0521] Of particular note, due to the spectrum of invertebrate pest control and economic importance, protecting agricultural crops from damage or injury caused by invertebrate pests by controlling and combating invertebrate pests is an embodiment of the present invention. The compounds of the present invention also protect leaves or other plant parts that are not in direct contact with the compound of Formula 1 or a composition comprising the compound due to their favorable transfer characteristics or systemicity in the plant.

[0522] Bioaccumulation of pesticides in non-target organisms is an important safety consideration, and it is generally desirable to limit systemic exposure and / or accumulation of pesticides and / or their metabolites in non-target organisms. For example, if a compound is to be applied to crop plants as an insecticide, it is desirable that the compound not accumulate in the plasma or fat of vertebrates.

[0523] Compounds of Formula 1 can exhibit favorable pharmacokinetic properties in vertebrates. In particular, compounds of Formula 1 have been found to be rapidly cleared from vertebrate plasma / blood and have low distribution into vertebrate fat, thereby reducing the potential for undesirable bioaccumulation. Of note is the fluorine atom at the 4-position of the phenyl ring attached to the 5-position of the isoxazoline ring.

[0524] The pharmacokinetic properties of the compound of formula 1 can be measured using a variety of assay schemes known in pharmacological science. In an exemplary method related to a single oral dose, three male rats and three female rats each receive a single dose of test substance via oral gavage. Blood is collected through the tail vein at 0.25, 0.5, 1, 2, 4, 8, 12 and 24 hours and then every 24 hours until death. In order to process the sample into plasma, blood is collected in a test tube containing ethylenediaminetetraacetic acid (EDTA) and centrifuged at a speed of about 3000 rpm to separate plasma from red blood cells. Alternatively, blood is collected using microcapillaries and distributed to a tube containing HPLC water (1: 1, v / v). Fat is also collected, homogenized and extracted to determine the concentration of the compound of formula 1 when it is killed. For example, compounds and / or metabolites with formula 1 in plasma or blood and fat are analyzed by high performance liquid chromatography (HPLC) and tandem mass spectrometry detection (LC / MS / MS) to determine the concentration of the test substance. Use nonlinear modeling software (e.g. Pharsight-A Certara TM Louis, MO, USA) to analyze plasma or blood pharmacokinetic data to determine the plasma / blood half-life, time to maximum plasma / blood concentration (T max ), maximum plasma / blood concentration (C max ) and the area under the plasma / blood concentration curve (AUC). Since fat analysis requires the sacrifice of rats, fat data are obtained at a single time point (i.e., the time when the rats were sacrificed). The fat: plasma or fat: blood ratio of the compound of Formula 1 is then determined.

[0525] Also noteworthy as embodiments of the present invention are compositions comprising a compound as described in any one of the preceding embodiments, as well as any other embodiments described herein, and any combination thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising at least one additional biologically active compound or agent.

[0526] Also noteworthy as embodiments of the present invention are compositions for controlling and combating invertebrate pests comprising a compound as described in any of the preceding embodiments and any other embodiments described herein, and any combination thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising at least one additional biologically active compound or agent. Embodiments of the present invention further include methods for controlling and combating invertebrate pests comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound as described in any of the preceding embodiments (e.g., as a composition described herein).

[0527] Embodiments of the present invention also include compositions comprising a compound as described in any of the preceding embodiments in the form of a soil drench liquid formulation. Embodiments of the present invention further include methods for controlling and combating invertebrate pests comprising contacting soil with a liquid composition as a soil drench comprising a biologically effective amount of a compound as described in any of the preceding embodiments.

[0528] Embodiments of the present invention also include a spray composition for controlling and combating invertebrate pests, the spray composition comprising a biologically effective amount of a compound as described in any of the preceding embodiments and a propellant. Embodiments of the present invention further include a bait composition for controlling and combating invertebrate pests, the bait composition comprising a biologically effective amount of a compound as described in any of the preceding embodiments, one or more food materials, an optional attractant, and an optional wetting agent. Embodiments of the present invention also include a device for controlling and combating invertebrate pests, the device comprising the bait composition and a housing adapted to contain the bait composition, wherein the housing has at least one opening sized to allow an invertebrate pest to pass through the opening, enabling the invertebrate pest to access the bait composition from a location external to the housing, and wherein the housing is further adapted to be placed in or near a location where the invertebrate pest may or is known to be active.

[0529] Embodiments of the invention also include methods for protecting seeds from invertebrate pests comprising contacting the seeds with a biologically effective amount of a compound as described in any of the preceding embodiments.

[0530] Embodiments of the present invention also include methods for controlling and combating invertebrate pests comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound having Formula 1 (e.g., as a composition described herein), with the proviso that these methods are not methods of medical treatment of humans by therapy.

[0531] The present invention also relates to methods wherein an invertebrate pest or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, optionally further comprising a biologically effective amount of at least one additional biologically active compound or agent, with the proviso that these methods are not methods of medical treatment of humans by therapy.

[0532] Compounds of Formula 1 can be prepared by one or more of the following methods and variations as described in Schemes 1-13. Unless otherwise indicated, the definitions of substituents in the compounds of Formulas 1-14 below are as defined above in the Summary of the Invention. The following abbreviations may be used: DMF is N,N-dimethylformamide, and DBU is 1,8-diazabicyclo[5.4.0]undec-7-ene.

[0533] Compounds of Formula 1 wherein X is S can be prepared by treating compounds of Formula 1 wherein X is O with a sulfurizing agent such as phosphorus pentasulfide or Lawesson's reagent (2,4-bis(p-methoxyphenyl)-1,3-dithiodiphosphatidine disulfide) by conditions and procedures well known to those skilled in the art of organic synthesis.

[0534] As shown in Scheme 1, compounds of formula 1, wherein X is O, can be prepared by reacting an amine intermediate of formula 2 with a carboxylic acid or acid derivative of formula 3 using an amide coupling reagent and conditions well known to those skilled in the art. For example, 3, wherein Y is chloro or fluoro, is combined with 2, optionally in the presence of a base such as sodium bicarbonate, potassium hydroxide, or an amine such as triethylamine, diisopropylethylamine, or pyridine, typically in a solvent or solvent mixture such as dichloromethane, ethyl acetate, tetrahydrofuran, or toluene, optionally in the presence of water, at a temperature from below ambient temperature to the boiling point of the reaction mixture. Intermediates 3 in which Y is a hydroxyl group can be reacted in the presence of an activating agent such as dicyclohexylcarbodiimide, 1,1'-carbonyldiimidazole, or (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) under conditions well known in the art. Intermediates 3 in which Y is an alkoxy group (typically methoxy or ethoxy) can be reacted in a solvent such as toluene or dichloromethane with the promotion of a trialkylaluminum reagent such as trimethylaluminum to prepare compounds of Formula 1.

[0535] Compounds of formula 3 are commercially available and can be prepared by procedures well known to those skilled in the art.

[0536] Solution 1

[0537]

[0538] As shown in Scheme 2, intermediate 2 can be prepared by reductive amination of a ketone of formula 4. Such reactions are well known in the art and are prepared by reacting a ketone 4 with an amine R 2 The reaction is carried out in a solvent such as methanol, ethanol, or water, usually with the addition of an acid promoter such as acetic acid. The conversion of 4 to 2 can be improved by the addition of an optional dehydrating agent such as titanium ethoxide or titanium isopropoxide, thereby forming an intermediate imine that is reduced by the subsequent addition of a reducing agent such as sodium borohydride or by exposure to hydrogen in the presence of a catalyst such as palladium on carbon under conditions well known in the art. The use of titanium tetraalkoxide and a reducing agent can facilitate the preparation of compounds wherein R 2 It is S(O)pR 7 or SO2NR 7 R 8 The compound of formula 1, and triethylsilane in combination with catalytic bismuth trichloride (as described in Tetrahedron Letters 2014, 55(10), 1829-1834) or triethylsilane in combination with catalytic antimony heptoxide (as described in Chemical Communications 2012, 48(66), 8276-8278) can be helpful in preparing the compound wherein R 2 It is C(O)OR 7 of a compound having Formula 1.

[0539] Option 2

[0540]

[0541] Get R 2 A variation of the method of Scheme 2 for compounds of Formula 2 that are hydrogen is shown in Scheme 3. Combining ketone 4 with 2-methyl-2-propanesulfinamide (which can be obtained as either the (R) or (S) enantiomer) with titanium tetraalkoxide, such as titanium tetraethoxide, under dehydrating conditions, followed by reduction with a reagent such as sodium borohydride, and subsequent removal of the sulfinyl group by exposure to an acid such as hydrochloric acid (typically in aqueous methanol, 1,4-dioxane, or tetrahydrofuran) provides amine 2 as predominantly one enantiomer. Single enantiomers of compounds of Formula 1 may offer advantages in activity, safety, and / or physical or other characteristics.

[0542] Option 3

[0543]

[0544] As shown in Scheme 4, compounds of formula 4 can be prepared by metallizing a compound of formula 5 and contacting it with a carbonyl-containing partner. Such metallization can be carried out by reacting with a strong lithium base such as lithium diisopropylamide or lithium tetramethylpiperidinium, or a magnesium base such as isopropylmagnesium chloride, optionally in a complex with lithium chloride and / or other metal salts to promote the metallization reaction. Suitable solvents are ethers such as diethyl ether or tetrahydrofuran, optionally in the presence of a cosolvent such as N,N'-dimethylpropylene urea (DMPU). The reaction can be carried out at a temperature from below -70°C to ambient temperature or slightly above ambient temperature. Suitable carbonyl compounds are, for example, "Weinreb amide" R3C(O)N(Me)OMe, which directly yields ketone 4 after hydrolysis.

[0545] Option 4

[0546]

[0547] Optionally, the carbonyl compound combined with the metallated pyrazole 5 may be an aldehyde R 3 CHO, as shown in Scheme 5, to provide intermediate alcohols 6. These alcohols can then be oxidized to provide ketones 4, such as by contact with chromium trioxide, manganese dioxide, or 1,1,1-triacetoxy-1,1-dihydro-1,2-benzidoyl-3(1H)-one (Dess-Martin hyperiodide, Martin reagent) in a solvent such as dichloromethane, acetonitrile, or acetone, or under many other reaction conditions and methods well known to those skilled in the art.

[0548] Option 5

[0549]

[0550] Alternatively, as shown in Scheme 6, alcohols of formula 6 can be used to prepare compounds wherein R 2 An amine of formula 2 that is hydrogen is converted to an azide 7 by reacting 6 with diphenylphosphoryl azide under Mitsunobu conditions by adding an azodicarboxylate such as diethyl azodicarboxylate (DEAD) and triphenylphosphine, typically in tetrahydrofuran solvent at a temperature slightly below ambient to ambient. Azide 7 can then be reduced to amine 2 using reagents such as triphenylphosphine in aqueous tetrahydrofuran, stannous chloride in methanol or ethanol, or via hydrogenation over a palladium catalyst in solvents such as methanol, ethanol, or ethyl acetate.

[0551] Option 6

[0552]

[0553] As shown in Scheme 7, where R 2Amines of formula 2 where R is hydrogen can be used to prepare 2 Not hydrogen, C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 7 or SO2NR 7 R 8

[00136] To further amines of Formula 2, this is performed by using reductive amination conditions similar to those of Scheme 2 and as is well known in the art.

[0554] Option 7

[0555]

[0556] As shown in scheme 8, pyrazole with formula 5 can be by pyrazole with formula 8 and group QL (wherein L is halogen, alkyl- or haloalkyl sulfonate, nitro or alkyl sulfonyl), optionally in the presence of a base promoter, and optionally in the presence of a metal catalyst to prepare the reaction. Possible optional bases include triethylamine, 1,8-diazabicyclo [5.4.0] 11 carbon -7- ene (DBU), potassium carbonate, cesium carbonate, sodium hydride or potassium tert-butoxide, and optional metal catalysts are typically copper or palladium, generally with other ligands such as N, N'-dimethylethylenediamine, 1,2-cyclohexanediamine or 2,2'-bipyridine for copper-promoted reaction, or aryl phosphine, alkyl phosphine or mixed alkyl / aryl phosphine ligands for palladium-promoted reaction. Typical solvents for these reactions include water, methanol, tert-butyl alcohol, tetrahydrofuran, dimethyl sulfoxide, dimethylformamide, 1,4-dioxane and toluene. Such reactions are well known to those skilled in the art.

[0557] Option 8

[0558]

[0559] Pyrazoles of formula 8 and groups QL are commercially available or readily prepared by methods known to those skilled in the art.

[0560] Alternatively, as shown in Scheme 9, compounds of Formula 1 can be prepared by combining a pyrazole of Formula 9 with a compound of Formula QL under the conditions described in Scheme 8 above.

[0561] Option 9

[0562]

[0563] Compounds of formula 9 can be prepared directly by methods analogous to those of Schemes 1 to 8, or in some cases advantageously by using a protecting group on the pyrazole as shown in Scheme 10 for the pyrazole of formula 10. Some examples of suitable protecting groups are benzyl or p-methoxybenzyl. These protecting groups are removed by methods well known in the art, such as by hydrogenation to remove the benzyl group, or treatment with a mild oxidizing agent such as ceric ammonium nitrate or an acid such as trifluoroacetic acid to remove the p-methoxybenzyl group or related groups.

[0564] Plan 10

[0565]

[0566] As shown in Scheme 11, where R 2 The compound of formula 1 wherein R is hydrogen may be 2 -L (wherein L is a suitable leaving group such as halogen, mesylate, or p-toluenesulfonate) is converted to other compounds of Formula 1. These reactions are typically carried out in the presence of a base promoter such as sodium hydride, potassium tert-butoxide, or potassium bis(trimethylsilyl)amide in a solvent such as tetrahydrofuran, dimethyl sulfoxide, or dimethylformamide.

[0567] Plan 11

[0568]

[0569] Alternatively, pyrazoles of formula 4 can be prepared as shown in Schemes 12 and 13. As shown in Scheme 12, hydrazones of formula 12 can be prepared by the reaction of glyoxal and substituted hydrazines in water or acetic acid as solvents, as described by Blake, James F. et al., World Intellectual Property Organization WO 2007103308. Typically, these reactions are carried out at room temperature to 125° C., and water can be removed by forming an azeotrope or distilling to give hydrazones of formula 12. Hydrazines of formula 14 are commercially available or readily prepared by methods known in the art.

[0570] Hydrazones of formula 12 can be cyclized to pyrazoles of formula 4 by condensation with compounds of formula 11 in which X is a halogen under basic conditions, as described by Taniguchi, Takahiko et al., World Intellectual Property Organization WO 2012020780. Typically, these reactions are carried out in solvents such as 1,4-dioxane at temperatures ranging from room temperature to 150°C. Unsubstituted pyrazoles can be further derivatized to compounds in which R is substituted under many other reaction conditions and methods well known to those skilled in the art. 4 or R 5 Various compounds having substituents such as bromine or cyano.

[0571] Plan 12

[0572]

[0573] Plan 13

[0574]

[0575] Those skilled in the art of organic synthesis will recognize that many substituents such as R 1 、R 2 、R 4 、R 5 As well as the substituents on Q can be converted to each other by reaction with suitable reagents through known chemistry of functional group transformations, and therefore are not described in detail here due to their familiarity. However, as a general illustration, some such transformations can be carried out under neutral conditions using electrophilic halogenating agents such as N-chlorosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, and N-fluorobenzenesulfonimide, or after removing the hydrogen atom from the substrate using a base such as lithium diisopropylamide, and replacing the hydrogen atom with a halogen. For the introduction of many other substituents, such as by free radical reactions or nucleophilic displacement, or for the introduction of groups based on cyano, carbonyl, amine, or sulphur, halogen is an extremely useful functional group, which is typically introduced using palladium, nickel, or copper catalysis. Other groups can be interconverted by reduction with various well-known reagents such as lithium tetrahydroaluminate or by hydrogenation over a palladium catalyst; dealkylation of alkoxy groups by contact with boron tribromide or aluminum trichloride; alkylation of oxygen-, nitrogen-, and sulfur-based groups with various reagents; nitration of aromatic and heteroaromatic rings; acylation of amines; sulfonylation of amines and hydroxy groups; or preparation of amides from carboxylic acids or esters, etc. Many of these interconversions are illustrated by the steps in the following examples.

[0576] Examples of intermediates that can be used to prepare the compounds of the present invention are shown in Tables I-1 to I-53. The following abbreviations are used in the following tables: Me means methyl, Et means ethyl, Ph means phenyl, C(O) means carbonyl, and CHO means formyl.

[0577] Table I-1

[0578]

[0579] Q is Q-1

[0580]

[0581]

[0582] Table I-2 is the same as Table I-1 except that Q is Q-2.

[0583] Table I-3 is the same as Table I-1 except that Q is Q-3.

[0584] Table I-4 is the same as Table I-1 except that Q is Q-4.

[0585] Table I-5 is the same as Table I-1 except that Q is Q-5.

[0586] Table I-6 is the same as Table I-1 except that Q is Q-6.

[0587] Table I-7 is the same as Table I-1 except that Q is Q-7.

[0588] Table I-8 is the same as Table I-1 except that Q is Q-8.

[0589] Table I-9 is the same as Table I-1 except that Q is Q-9.

[0590] Table I-10 is the same as Table I-1 except that Q is Q-10.

[0591] Table I-11 is the same as Table I-1 except that Q is Q-11.

[0592] Table I-12 is the same as Table I-1 except that Q is Q-12.

[0593] Table I-13 is the same as Table I-1 except that Q is Q-13.

[0594] Table I-14 is the same as Table I-1 except that Q is Q-14.

[0595] Table I-15 is the same as Table I-1 except that Q is Q-15.

[0596] Table I-16 is the same as Table I-1 except that Q is Q-16.

[0597] Table I-17 is the same as Table I-1 except that Q is Q-17.

[0598] Table I-18 is the same as Table I-1 except that Q is Q-18.

[0599] Table I-19 is the same as Table I-1, except that Q is Q-19.

[0600] Table I-20 is the same as Table I-1 except that Q is Q-20.

[0601] Table I-21 is the same as Table I-1 except that Q is Q-21.

[0602] Table I-22 is the same as Table I-1 except that Q is Q-22.

[0603] Table I-23 is the same as Table I-1 except that Q is Q-23.

[0604] Table I-24 is the same as Table I-1 except that Q is Q-24.

[0605] Table I-25 is the same as Table I-1 except that Q is Q-25.

[0606] Table I-26 is the same as Table I-1 except that Q is Q-26.

[0607] Table I-27

[0608]

[0609] In addition to the title " Table I-1 Table I-27 is the same as Table I-1, except that the structure below is replaced by the structure shown above.

[0610] In addition to the title " Table I-1 The structure under " Table I-27 " Tables I-28 to I-53 are the same as Tables I-2 to I-26, except for the structural substitutions shown below.

[0611] It should be recognized that some of the reagents and reaction conditions described above for preparing the compound with formula 1 may not be compatible with some functional groups present in the intermediate. In these cases, the protection / deprotection sequence or functional group mutual conversion incorporated into the synthesis will help to obtain the desired product. The use and selection of protecting groups will be apparent to those skilled in the art of chemical synthesis (see, for example, Greene, TW; Wuts, PGM Protective Groups in Organic Synthesis [protective groups in organic synthesis], 2nd edition; Wiley Press: New York, 1991). Those skilled in the art will recognize that, in some cases, after introducing the reagents depicted in each scheme, additional conventional synthesis steps not described in detail may be required to complete the synthesis of the compound with formula 1. Those skilled in the art will also recognize that it may be necessary to carry out the combination of the steps shown in the above scheme in an order different from the specific sequence presented by the compound with formula 1.

[0612] Those skilled in the art will also recognize that the compounds of Formula 1 and intermediates described herein can be subjected to a variety of electrophilic, nucleophilic, free radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0613] Without further elaboration, it is believed that one skilled in the art can utilize the present invention to the greatest extent possible using the foregoing description. Therefore, the following synthesis examples should be interpreted as merely illustrative and not limiting of this disclosure in any way. The steps in the following synthesis examples illustrate the procedures for each step in the overall synthesis transformation, and the starting materials for each step are not necessarily prepared by the specific preparative experiments whose procedures are described in other examples or steps. Percentages are by weight, except for chromatographic solvent mixtures or otherwise specified. Unless otherwise specified, the parts and percentages of chromatographic solvent mixtures are by volume. 1 H NMR spectra are reported in ppm downfield from tetramethylsilane; "s" means singlet, "d" means doublet, "t" means triplet, "q" means quartet, "m" means multiplet, "dd" means two doublets, "dt" means two triplets, and "br s" means broad singlet. DMF means N,N-dimethylformamide, and DMSO means dimethyl sulfoxide. Compound numbers refer to Index Table A.

[0614] Synthesis Example 1

[0615] N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl) Preparation of 4-(2-amino-4-methyl)benzamide (Compound 9)

[0616] Step A: Preparation of 5-bromo-2-(3-nitropyrazol-1-yl)pyridine

[0617] In a microwave vial, 3-nitro-1H-pyrazole (2.00g, 17.7mmol, 1eq) and 2,5-dibromopyridine (4.10g, 17.7mmol, 1eq) are combined in N,N-dimethylformamide (15mL), and cesium carbonate (5.7g, 17.7mmol, 1eq) is added. The reaction mixture is irradiated at 140°C for 2 hours under microwave and monitored by thin layer chromatography. When the starting material is consumed, the reaction mixture is poured into cold water (100mL), and the solid obtained is collected on a glass frit and washed with water. Drying under reduced pressure gives 5-bromo-2-(3-nitropyrazole-1-yl)pyridine (3.5g, 74%), which is a pale solid melted at 215°C-218°C.

[0618] 1 H NMR(DMSO-d6)δ8.84(d,1H),8.73(m,1H),8.35(m,1H),7.96(m,1H),7.35(d,1H).

[0619] LCMS: m / z: 269 / 271 [M+H]+

[0620] Step B: Preparation of 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethanone

[0621] A mixture of 5-bromo-2-(3-nitropyrazole-1-yl)pyridine (5.5 g, 20.522 mmol, 1 eq) in tetrahydrofuran (350 mL) prepared as in step 1 was cooled to -30 ° C, lithium diisopropylamide (2 M solution in tetrahydrofuran, 15.4 mL, 30.8 mmol, 1.5 eq) was added dropwise, and the mixture was stirred at -30 ° C. After 40 minutes, N-methoxy-N-methyl-acetamide (3.1 g, 30.8 mmol, 1.5 eq) was added, and the reaction mixture was slowly heated to ambient temperature over 2 hours. Saturated aqueous ammonium chloride solution (100 mL) was added, and this mixture was extracted twice with each 200 mL ethyl acetate. The combined organic phase was washed twice with each 100 mL saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to obtain residue. This residue was subjected to combi-flash chromatography eluting with a gradient of 0% to 50% ethyl acetate in petroleum ether to afford 1-[2-(5-bromo-2-pyridinyl)-5-nitro-pyrazol-3-yl]ethanone (2.3 g, 36%) as a yellow solid melting at 117°C-120°C. 1 H NMR(CDCl3)δ8.52(m,1H),8.07(m,1H),7.70(m,1H),7.09(m,1H),2.57(s,3H). LCMS:m / z:311 / 313[M+H]+

[0622] Step C: Preparation of 1-[2-(5-bromo-2-pyridinyl)-5-nitro-pyrazol-3-yl]-N-methyl-ethylamine

[0623] To a mixture of 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethanone (2.8 g, 9.0 mmol, 1 eq) and titanium tetraethoxide (2.6 g, 11.7 mmol, 1.3 eq) in methanol (77 mL) was added methylamine (30% ethanol solution, 2.8 mL, 27 mmol, 3 eq). The reaction mixture was stirred at ambient temperature for 16 hours and then heated at 60° C. for 2 hours. The reaction mixture was cooled to 0° C. and sodium borohydride (0.341 g, 9.03 mmol, 1.0 eq) was added. The reaction mixture was stirred at ambient temperature for 2 hours and then poured into ice-cold water (200 mL) and extracted twice with 150 mL portions of ethyl acetate. The combined organic phases were washed twice with 100 mL of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to afford crude 1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]-N-methyl-ethanamine (1.8 g, 62%) as an impure brown semisolid melting at 125-128° C. LCMS: m / z: 326 / 328 [M+H] +, indicating one component. This was used directly in the reaction of step 4 below.

[0624] Step D: N-[1-[2-(5-bromo-2-pyridinyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)- ... Preparation of (4-fluoromethyl)benzamide

[0625] To a mixture of 1-[2-(5-bromo-2-pyridinyl)-5-nitro-pyrazol-3-yl]-N-methyl-ethylamine (1.8 g, 5.5 mmol, 1 eq) and 3,5-bis(trifluoromethyl)benzoic acid (1.70 g, 6.65 mmol, 1.2 eq) in N,N-dimethylformamide (18 mL) was added 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 3.15 g, 8.31 mmol, 1.5 eq) and diisopropylethylamine (2.0 mL, 11 mmol, 2 eq) prepared as in step 3. The reaction mixture was stirred at ambient temperature for 16 hours, poured into cold water (80 mL), and extracted twice with 150 mL portions of ethyl acetate. The combined organic phases were washed twice with 100 mL of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. This residue was purified by combi-flash chromatography using a gradient of 0% to 50% ethyl acetate in petroleum ether to obtain N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (1.8 g, 58%), a compound of the present invention, as an off-white solid that melted at 174°C-177°C. A certain amount of the product of step B co-eluted with this product. 1 H NMR(CDCl3)δ8.45(m,1H),8.1(m,1H),7.9(m,2H),7.4-7.5(m,2H),7.2(m,1H),6.5(q,1H),2.60(s,3H),1.74(d,3H).

[0626] LCMS: m / z: 566 / 568 [M+H]+

[0627] Synthesis Example 2

[0628] N-[1-[5-amino-2-(5-bromo-2-pyridinyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl) Preparation of benzamide (Compound 11)

[0629] To a mixture of N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl] ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (1.10 g, 1.95 mmol, 1 eq) in ethanol (50 mL) and water (25 mL) as prepared in Example 1, ammonium chloride (415 mg, 7.79 mmol, 4 eq) and iron powder (217 mg, 3.89 mmol, 2 eq) were added. The reaction mixture was stirred at reflux for 4 hours and then allowed to cool to ambient temperature. The reaction mixture was diluted with ethyl acetate (100 mL), filtered through a pad of diatomaceous earth filter aid, and the filter cake was washed with ethyl acetate (100 mL). The combined organic layer was washed twice with 100 mL of saturated sodium chloride aqueous solution per portion, dried over sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. The crude material was purified by combi-flash chromatography eluting with a gradient of 0%-80% ethyl acetate / petroleum ether to give N-[1-[5-amino-2-(5-bromo-2-pyridinyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (800 mg, 80%), the product of the present invention, as a brown solid melting at 139°C-141°C. 1 H NMR(DMSO-d6,90℃)δ7.8-8.25(m,3H),7.4-7.85(m,3H),6.30(q,1H),5.97(s,1H),5.29(s,2H),3.32(s,3H),2.50(d,3H).

[0630] LCMS: m / z: 536 / 538 [M+H]+

[0631] Synthesis Example 3

[0632] N-[1-[5-acetylamino-2-(5-bromo-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)pyrazol-3-yl]ethyl]- Preparation of 2-(4-methyl)benzamide (Compound 15):In a 20mL scintillation tube, by N-{1-[5-amino-2-(5-bromopyridin-2-yl)pyrazol-3-yl]ethyl}-N-methyl-3,5-bis(trifluoromethyl)benzamide (96.7mg, 0.18mmol, 1eq) in tetrahydrofuran (0.60mL) as prepared in Example 2, and cooled in an ice bath.Triethylamine (0.077mL, 0.541mmol, 3eq) and acetyl chloride (0.016mL, 0.22mmol, 1.2eq) were added dropwise. The mixture was stirred at ambient temperature for 16 hours, diluted with water, and extracted twice with two portions of approximately 10mL ethyl acetate. The organic phase was washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and concentrated under reduced pressure to give a thick residue. The crude residue was subjected to automated flash chromatography eluting with a 0%-50% ethyl acetate / hexane gradient to isolate N-[1-[5-acetylamino-2-(5-bromo-2-pyridinyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (84 mg), a compound of the present invention, as a brown solid.

[0633] 1 H NMR(CDCl3)δ8.35(m,1H),8.20(m,1H),7.85-7.96(m,2H),7.63(m,1H),7.45(brs,2H),7.11(m,1H),6.50(br m,1H),2.53(s,3H),2.20(s,3H),1.67(d,3H).

[0634] LCMS: m / z: 578 / 580 [M+H]+

[0635] Synthesis Example 4

[0636] N-[1-[5-amino-2-(5-bromo-2-pyridyl)-4-iodo-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trimethylol)- Preparation of (4-fluoromethyl)benzamide (Compound 10)

[0637] To a mixture of N-{1-[5-amino-2-(5-bromopyridin-2-yl)pyrazol-3-yl]ethyl}-N-methyl-3,5-bis(trifluoromethyl)benzamide (800 mg, 1.5 mmol, 1 eq) in N,N-dimethylformamide (8 mL) prepared as in Example 2 was added N-iodosuccinimide (415 mg, 1.64 mmol, 1.1 eq). The reaction mixture was stirred at 40 ° C for 3 hours and then poured into cold water (100 mL). The obtained solid was collected on a glass frit and washed with water and dried under reduced pressure to obtain the compound of the present invention, N-[1-[5-amino-2-(5-bromo-2-pyridinyl)-4-iodo-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (780 mg, 78%), which was an off-white solid that melted at 159 ° C -162 ° C. 1 H NMR(DMSO-d6,91℃)δ8.33(s,1H),8.05(m,1H),7.96(m,1H),7.69(s,2H),7.48(m,1H),6.17(q,1H),4.84(br,2H),2.96(s,3H),1.72(s,3H).

[0638] LCMS: m / z: 662 / 664 [M+H]+

[0639] Synthesis Example 5

[0640] N-[1-[3-amino-4-cyano-1-(5-cyano-2-pyridinyl)-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5 Preparation of bis(trifluoromethyl)benzamide (Compound 14)

[0641] In a microwave vial, a mixture of N-[1-[5-amino-2-(5-bromo-2-pyridinyl)-4-iodo-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (400 mg, 0.605 mmol, 1 eq) and zinc cyanide (283 mg, 2.42 mmol, 4 eq) in N,N-dimethylformamide (4 mL) was degassed with argon for 15 minutes, followed by the addition of 1,1'-bis(diphenylphosphino)ferrocene (67 mg, 0.12 mmol, 0.2 eq) and tris(dibenzylideneacetone)dipalladium(0) (55 mg, 0.060 mmol, 0.1 eq). The reaction mixture was irradiated under microwave at 120° C. for 1.5 hours and then poured into ice-cold water (20 mL) and extracted with two 50 mL portions of ethyl acetate. The combined organic layers were washed twice with 50 mL of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. The crude material was purified by combi-flash chromatography using a gradient of 0%-80% ethyl acetate / petroleum ether to obtain N-[1-[5-amino-4-cyano-2-(5-cyano-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (220 mg, 71%), a compound of the present invention, as an off-white solid that melts at 191°C-194°C. IR 2222 cm -1

[0642] 1 H NMR(DMSO-d6,89℃)δ8.76(s,1H),8.38(m,1H),8.06(s,1H),7.8-7.9(m,3H),6.35(q,1H),5.84(s,2H),2.96(s,3H),2.48(d,3H).

[0643] LCMS: m / z: 508 [M+H]+

[0644] Synthesis Examples 6 and 7

[0645] N-[1-[4-cyano-1-(5-cyano-2-pyridinyl)-3-(methylamino)-1H-pyrazol-5-yl]ethyl]-N-methyl 3,5-bis(trifluoromethyl)benzamide (Compound 12) and N-[1-[4-cyano-2-(5-cyano-2-pyridyl)-5-(difluoromethyl)benzamide] Preparation of [(1-methylamino)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 13)

[0646] In a microwave vial, to a mixture of N-[1-[5-amino-4-cyano-2-(5-cyano-2-pyridyl)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (80 mg, 0.16 mmol, 1 eq) and potassium carbonate (43 mg, 0.32 mmol, 2 eq) in N,N-dimethylformamide (2 mL) was added iodomethane (33 mg, 0.23 mmol, 1.5 eq). The reaction mixture was irradiated under microwave at 100 ° C for 1 hour, poured into ice-cold water (20 mL), and extracted with two 50 mL portions of ethyl acetate. The combined organic layers were washed twice with 50 mL of saturated sodium chloride aqueous solution each, dried over sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. The crude material was purified by combi-flash chromatography using a gradient of 0% to 80% ethyl acetate / petroleum ether to afford N-[1-[4-cyano-2-(5-cyano-2-pyridinyl)-5-(methylamino)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 12), a compound of the present invention (20 mg, 24%), as a light brown solid. (Compound 12).

[0647] 1 H NMR(CDCl3)δ8.6(br,1H),8.07(br,2H),7.82-7.95(br m,3H),6.6(br,1H),4.22(q,1H),3.1(s,3H),3.02(d,3H),1.83(d,3H).

[0648] LCMS:m / z:522[M+H]+

[0649] Also isolated from this reaction was the compound of the present invention, N-[1-[4-cyano-2-(5-cyano-2-pyridinyl)-5-(dimethylamino)pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 13) (15 mg, 17%), as an off-white solid (Compound 13).

[0650] 1 H NMR(CDCl3)δ8.62(br,1H),8.07(br,2H),7.85-7.95(br,3H),6.58(br,1H),3.16(s,3H),3.12(s,6H),1.85(d,3H). LCMS:m / z:536[M+H]+

[0651] Synthesis Example 8

[0652] 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl] Preparation of methyl pyridine-3-carboxylate (Compound 30):In a steel reactor, a mixture of N-[1-[2-(5-bromo-2-pyridyl)-5-nitro-pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (500 mg, 0.884 mmol, 1 eq), prepared as in Example 1, and triethylamine (0.255 mL, 1.76 mmol, 2 eq) in N,N-dimethylformamide (2 mL) and methanol (10 mL) was degassed with argon for 15 minutes. [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1 complex with dichloromethane) (72 mg, 0.088 mmol, 0.1 eq) was added. Carbon monoxide gas was introduced at 150 psi and the mixture was heated at 100°C for 16 hours. The reaction mixture was poured into cold water (80 mL) and extracted twice with 150 mL portions of ethyl acetate. The combined organic phases were washed twice with 100 mL of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to give a residue. The crude residue was purified by combi-flash chromatography using a gradient of 0% to 80% ethyl acetate in petroleum ether to give methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (300 mg, 65%), a compound of the present invention, as a brown solid melted at 171° C.-174° C.

[0653] 1 H NMR(DMSO-d6,90℃)δ8.55(br,1H),8.29(d,1H),8.00(s,1H),7.75(d,1H),7.61(s,2 H),6.3(br,1H),6.05(s,1H),5.12(s,2H),3.83(s,3H),2.65(br,3H),1.57(d,3H).

[0654] LCMS: m / z: 516 [M+H]+

[0655] Synthesis Example 9

[0656] 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-iodo-pyrazole- Preparation of methyl 1-pyridine-3-carboxylate (Compound 23):To a mixture of methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (1.5 g, 2.9 mmol, 1 eq) in N,N-dimethylformamide (20 mL) prepared as in Example 8 was added N-iodosuccinimide (0.72 g, 3.2 mmol, 1.1 eq), and the reaction mixture was stirred at 40° C. for 3 hours and then poured into cold water (200 mL). The obtained solid was collected on a glass frit, washed with water, and dried under reduced pressure to give 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-iodo-pyrazol-1-yl]pyridine-3-carboxylic acid methyl ester (1.43 g, 72%), a compound of the present invention, as a white solid that melts at 163°C-169°C.

[0657] 1 H NMR (DMSO-d6, 89℃) δ 8.71 (s, 1H), 8.30 (m, 1H), 7.94 (s, 1H), 7.67 (m 3H), 6.35 (q, 1H), 4.99 (s, 2H), 3.87 (s, 3H), 2.98 (s, 3H), 1.75 (d, 3H).

[0658] LCMS: m / z: 642 [M+H]+

[0659] Synthesis Example 10

[0660] 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrrolidone Preparation of methyl [oxazol-1-yl]pyridine-3-carboxylate (Compound 24) :

[0661] In a microwave vial, a mixture of methyl 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-iodo-pyrazol-1-yl]pyridine-3-carboxylate (1.0 g, 1.56 mmol, 1 eq) and zinc cyanide (0.365 g, 3.12 mmol, 2 eq) in N,N-dimethylformamide (15 mL) was degassed with argon for 15 minutes, followed by the addition of 1,1'-bis(diphenylphosphino)ferrocene (0.172 g, 0.312 mmol, 0.2 eq) and tris(dibenzylideneacetone)dipalladium(0) (0.142 g, 0.156 mmol, 0.1 eq). The reaction mixture was irradiated under microwave conditions at 120° C. for 1.5 hours, then poured into ice-cold water (80 mL) and extracted twice with 100 mL portions of ethyl acetate. The combined organic phase was washed twice with 50 mL of saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure to obtain a residue. The crude residue was purified by combi-flash chromatography using a gradient of 0%-50% ethyl acetate / petroleum ether to obtain compound 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylic acid methyl ester (700 mg, 82%), a compound of the present invention, as a pale white solid molten at 229° C.-233° C.

[0662] 1 H NMR(DMSO-d6,89℃)δ8.79(s,1H),8.42(d,1H),8.03(s,1H),7.77-7.85(m,3H),6.38(q,1H),5.74(s,2H),4.02(s,3H),2.92(s,3H),1.73(d,3H).

[0663] LCMS: m / z: 541[M+H]+

[0664] Synthesis Example 11

[0665] 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrrolidone Preparation of [oxazol-1-yl]pyridine-3-carboxylic acid (Compound 25):

[0666] To a mixture of 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylic acid methyl ester (800 mg, 1.48 mmol, 1 eq) in tetrahydrofuran (40 mL) and water (20 mL) was added lithium hydroxide monohydrate (124 mg, 2.96 mmol, 2 eq). The reaction mixture was stirred at ambient temperature for 16 hours, poured into cold water (20 mL), and extracted twice with 50 mL portions of diethyl ether. The aqueous layer was acidified to pH 4 with 1N aqueous hydrochloric acid solution, and the resulting precipitate was collected on a glass frit, washed with water, and dried under reduced pressure to give 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylic acid (650 mg, 83%), a compound of the present invention, as an off-white solid melting at 193° C.-196° C.

[0667] 1 H NMR (DMSO-d6, 90℃) δ8.74(s,1H),8.34(m,1H),8.02(s,1H),7.83(s,2H),7.64(m,1H),6.31(q,1H),5.63(s.2H),2.91(s,3H),1.69(d,3H).

[0668] LCMS: m / z: 527 [M+H]+

[0669] Synthesis Example 12

[0670] N-[1-[3-amino-4-cyano-1-[5-(4-morpholinylcarbonyl)-2-pyridinyl]-1H-pyrazol-5-yl]ethyl]- Preparation of N-methyl-3,5-bis(trifluoromethyl)benzamide (Compound 26):

[0671] To a mixture of 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]-4-cyano-pyrazol-1-yl]pyridine-3-carboxylic acid (700 mg, 1.33 mmol, 1 eq), morpholine (115 mg, 1.73, 1.3 eq) and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 758 mg, 2.0 mmol, 1.5 eq) in N,N-dimethylformamide (15 mL) was added diisopropylethylamine (0.73 mL, 4.0 mmol, 3 eq). The reaction mixture was stirred at ambient temperature for 16 hours and poured into cold water (60 mL). The obtained solid was collected on a glass frit, washed with water, and dried under reduced pressure to obtain compound N-[1-[5-amino-4-cyano-2-[5-(morpholine-4-carbonyl)-2-pyridyl]pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (500 mg, 63%), a compound of the present invention, which is a white solid that melts at 211°C-214°C.

[0672] 1 H NMR(DMSO-d6,89℃)δ8.39(s,1H),8.06(m,1H),8.01(m,1H),7.89(s,2H),7.76(m,1 H),6.35(q,1H),5.66(s.2H),3.58(m,4H),3.48(m,4H),2.93(s,3H),1.70(d,3H).

[0673] LCMS: m / z: 596 [M+H]+

[0674] Synthesis Example 13

[0675] 6-[3-Acetylamino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazole-1- Preparation of methyl]pyridine-3-carboxylate (Compound 27):

[0676] Under ice bath cooling, to 6-[3-amino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylic acid methyl ester (300mg, 0.58mmol, 1eq) and triethylamine (0.167mL, 1.17mmol, 2eq) in dichloromethane (10mL) as prepared in Example 8, acetyl chloride (0.061mL, 0.87mmol, 1.5eq) is added. The reaction mixture is stirred at ambient temperature for 16 hours, then merged with ice-cold water (20mL), and extracted with two 50mL portions of dichloromethane. The combined organic layer is washed twice with each 50mL saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. The crude material was purified by combi-flash chromatography eluting with a gradient of 0%-70% ethyl acetate / petroleum ether to afford compound 6-[3-acetylamino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylic acid methyl ester (150 mg, 46%), a compound of the present invention, as a white solid melting at 266°C-269°C.

[0677] 1 H NMR(DMSO-d6,89℃)δ10.44(s,1H),8.64(br,1H),8.41(d,1H),7.99(m,1H),7.82(d,1H),7.57(s,2H),6.99(s,1H),6.35(br m,1H),3.86(s,3H),2.55-2.85(br,3H),2.06(s,3H),1.62(d,3H).

[0678] LCMS: m / z: 558 [M+H]+

[0679] Synthesis Example 14

[0680] 6-[3-Acetylamino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazole-1- Preparation of [3-amino]pyridine-3-carboxylic acid (Compound 28):

[0681] To a mixture of methyl 6-[3-acetylamino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylate (120 mg, 0.215 mmol, 1 eq) in tetrahydrofuran (10 mL) and water (5 mL), prepared as in Example 13, was added lithium hydroxide monohydrate (27 mg, 0.65 mmol, 3 eq). The reaction mixture was stirred at ambient temperature for 16 hours, poured into cold water (15 mL), and extracted twice with 20 mL portions of diethyl ether. The aqueous layer was acidified to pH 4 with 1N aqueous hydrochloric acid solution, and the obtained solid was collected on a glass frit, washed with water, and dried under reduced pressure to give 6-[3-acetylamino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylic acid (100 mg, 86%), a compound of the present invention, as an off-white solid melting at 266° C.-269° C.

[0682] 1 H NMR(DMSO-d6,28℃)δ13.4(br,1H),10.83(s,1H),8.71(s,1H),8.48(d,1H),8.15(s,1H),7 .84(d,1H),7.41(s,2H),7.05(s,1H),6.44(m,1H),2.39(s,3H),2.07(s,3H),1.60(d,3H).

[0683] LCMS: m / z: 544 [M+H]+

[0684] Synthesis Example 15

[0685] N-[1-[5-acetylamino-2-[5-(morpholine-4-carbonyl)-2-pyridinyl]pyrazol-3-yl]ethyl]-N-methyl- Preparation of 3,5-bis(trifluoromethyl)benzamide (Compound 21) :

[0686] To a mixture of 6-[3-acetylamino-5-[1-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]ethyl]pyrazol-1-yl]pyridine-3-carboxylic acid (100 mg, 0.183 mmol, 1 eq), morpholine (20 mg, 0.24 mmol, 1.3 eq) and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 104 mg, 0.275 mmol, 1.5 eq) in N,N-dimethylformamide (3 mL) was added diisopropylethylamine (0.10 mL, 0.55 mmol, 3 eq). The reaction mixture was stirred at ambient temperature for 16 hours and poured into cold water (20 mL). The obtained solid was collected on a glass frit, washed with water, and dried under reduced pressure to give N-[1-[5-acetylamino-2-[5-(morpholine-4-carbonyl)-2-pyridyl]pyrazol-3-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide (103 mg, 46%), a compound of the present invention, as a white solid that melts at 276°C-279°C.

[0687] 1 H NMR(DMSO-d6,90℃)δ10.36(s,1H),8.24(br s,1H),8.02(s,1H),8.00(d,1H),7.75(d,1H),7.69(s,2H),6.95(s,1H),6.32(b r,1H),3.55(br,4H),3.44(br,4H),2.6-2.8(br,3H),2.06(s,3H),1.60(d,3H).

[0688] LCMS: m / z: 613 [M+H]+

[0689] Synthesis Example 16

[0690] N-[1-[4-cyano-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl) Preparation of 4-(2-amino-4-methyl)benzamide (Compound 7):

[0691] Step A: Preparation of (2E)-2-(2-pyridylhydrazono)acetaldehyde

[0692] At ambient temperature, under agitation, a solution of 2-pyridylhydrazine (5.0 g, 45.45 mmol, 1.0 eq) in water (5 mL) is added into 40% glyoxal (6.5 mL, 181.8 mmol, 4.0 eq). Reaction mixture is heated to 100 ° C and continued for 4 hours, then cooled to ambient temperature. Precipitated solid is collected on glass frit, and vacuum dried to obtain grey solid (2E) -2- (2-pyridylhydrazono) acetaldehyde (5.8 g, 85%). 1H NMR(DMSO) δ12.058(bs,NH),9.509(d,1H),8.253(d,1H),7.804(m,1H),7.510(d,1H),7.357(d,1H),7.025(t,1H).

[0693] Step B: Preparation of 1-[2-(2-pyridyl)pyrazol-3-yl]ethanone

[0694] To a mixture of (2E)-2-(2-pyridylhydrazono)acetaldehyde (5.8 g, 38.9 mmol, 1.0 eq) in 1,4-dioxane (50 mL) was added potassium carbonate (13.4 g, 97.3 mmol, 2.5 eq) and chloroacetone (4.88 mL, 58.3 mmol, 1.5 eq) at ambient temperature. The reaction mixture was heated at 80 ° C for 5 hours, concentrated under reduced pressure, diluted with water (100 mL), and extracted twice with two 150 mL portions of ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crude solid was purified by column chromatography on silica gel (40 g) using combi-flash, eluting with 40% ethyl acetate / petroleum ether to give 1-[2-(2-pyridyl)pyrazol-3-yl]ethanone (5.1 g, 70%) as an off-white solid. 1 H NMR(DMSO-d6)δ8.46(d,1H),8.05(d,1H),7.84(s,1H),7.68(d,1H),7.48(d,1H),7.14(d,1H),2.49(s,3H)

[0695] Step C: Preparation of 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethanone

[0696] To a solution of 1- [2- (2- pyridyl) pyrazol-3-yl] ethanone (2.00 g, 10.6 mmol, 1.0 eq) in anhydrous N, N-dimethylformamide (20 mL) was added N- bromosuccinimide (2.00 g, 11.7 mmol, 1.1 eq) at 0 ° C. The resulting reaction mixture was stirred at 0 ° C to ambient temperature for 16 hours, quenched with water (50 mL), and extracted twice with 100 mL of ethyl acetate each. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. The crude material was purified by silica gel column chromatography (24 g), eluted with 20% ethyl acetate / petroleum ether to obtain 1- [4- bromo-2- (2- pyridyl) pyrazol-3-yl] ethanone (1.8 g, 64%) as an off-white solid. 1H NMR(DMSO-d6)δ8.44(d,1H),8.08(m,2H),7.87(d,1H),7.46(t,1H),2.48(s,3H)

[0697] Step D: Preparation of N-[1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethyl]-1-cyclopropyl-methylenemethanamine Preparation

[0698] To a solution of 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethanone (1.0 g, 3.7 mmol, 1.0 eq) in anhydrous tetrahydrofuran (20 mL) was added titanium tetraethoxide (3.4 g, 15.0 mmol, 4.0 eq) and cyclopropylmethylamine (236 mg, 4.15 mmol, 1.1 eq) at ambient temperature. The resulting reaction mixture was heated at 70° C. for 16 hours, water (50 mL) and ethyl acetate (200 mL) were added, and the mixture was passed through a filtration oven. The mixture was filtered through a pad of 4% paraffin wax. The organic layer was separated and washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. The crude material was purified by silica gel column chromatography (24 g) eluting with 50% ethyl acetate / petroleum ether to obtain 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanamine (0.6 g, 55%) as a brown solid. 1 H NMR(DMSO-d6)δ8.41(d,1H),8.03(m,2H),7.90(d,1H),7.40(t,1H),2.88(m,1H) ,2.67(m,1H),2.50(s,3H),1.18(m,1H),0.86(m,1H),0.29(m,2H),-0.14(m,1H)

[0699] Step E: Preparation of 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanamine

[0700] To a solution of 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanamine (100 mg, 0.31 mmol, 1.0 eq) in methanol (5 mL) was added cerium (III) chloride (115 mg, 0.466 mmol, 1.5 eq) at 0° C. with stirring. After 15 minutes, sodium borohydride (29 mg, 0.77 mmol, 2.5 eq) was added portionwise at 0° C., and the mixture was stirred for 16 hours. The reaction mixture was poured into ice-cold water (50 mL) and ethyl acetate (200 mL) and filtered. The organic layer was separated and washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain crude 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanamine (155 mg), which was used in the next step without further purification.

[0701] Step F: N-[1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(tris- Preparation of (4-fluoromethyl)benzamide

[0702] To a solution of 3,5-bis(trifluoromethyl)benzoic acid (600 mg, 2.3 mmol, 1.0 eq) in anhydrous DMF (140 mL) at ambient temperature were added 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU, 1.32 g, 3.4 mmol, 1.5 eq), crude 1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]-N-(cyclopropylmethyl)ethanamine (821 mg, 2.5 mmol, 1.1 eq) and diisopropylethylamine (1 mL, 5.8 mmol, 2.5 eq). The resulting reaction mixture was stirred at ambient temperature for 16 hours, and 150 mL of water was added. This mixture is extracted twice with each 200mL ethyl acetate, and the combined organic layers are washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. The crude material is purified by combi-flash chromatography on a silica gel column (40g), eluting with 20% ethyl acetate / petroleum ether to obtain N-[1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide (620mg, 48%) as an off-white solid. NMR(DMSO-d6)δ8.39(s,1H),8.12(s,1H),8.03(s,1H),7.86(m,1H),7.60(s,2H) ,7.45(m,2H),6.28(m,1H),3.06(m,2H),1.86(d,3H),0.66(m,3H),0.35(m,2H).

[0703] Step G: N-[1-[4-cyano-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-diol Preparation of (trifluoromethyl)benzamide

[0704] To a solution of N-[1-[4-bromo-2-(2-pyridyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide (300 mg, 0.53 mmol, 1.0 eq) in anhydrous N,N-dimethylformamide (3 mL) was added copper(I)cyanide (71 mg, 0.8 mmol, 1.5 eq) in a sealed tube at ambient temperature. The resulting reaction mixture was stirred at 160° C. for 24 hours. Water (50 mL) was added and the mixture was extracted twice with 200 mL portions of ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude residue. The crude material was purified by preparative HPLC to afford N-[1-[4-cyano-2-(2-pyridinyl)pyrazol-3-yl]ethyl]-N-(cyclopropylmethyl)-3,5-bis(trifluoromethyl)benzamide (113 mg, 41%) as an off-white solid. 1 H NMR(DMSO-d6)δ8.49(s,1H),8.37(s,1H),8.18(m,1H),8.12(m,1H),7.82(s,1H),7.68 (s,2H),7.56(m,1H),6.26(m,1H),2.96(m,2H),1.90(d,3H),1.23(m,3H),0.34(m,2H).

[0705] Synthesis Example 17

[0706] N-[1-(4-cyano-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzene Preparation of formamide (Compound 82)

[0707] Step A: Preparation of 2-(3-methoxypyrazol-1-yl)pyrimidine

[0708] A mixture of cesium carbonate (30.2 g, 92.7 mmol, 1.2 eq), 3-methoxy-1H-pyrazole (7.58 g, 77.3 mmol, 1 eq), 2-chloropyrimidine (8.85 g, 77.3 mmol, 1 eq) and N,N-dimethylformamide (155 mL) was heated to 120 ° C and stirred for 16 hours. The reaction was cooled to room temperature and diluted with water (150 mL). Toluene (150 mL) was added and the mixture was concentrated under reduced pressure on a rotary evaporator. This procedure was repeated, and the resulting aqueous phase was then extracted twice with ethyl acetate (2×150 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure on celite. The residue was purified by combi-flash chromatography using a gradient of 50% to 70% ethyl acetate in hexane to obtain the desired product, 2-(3-methoxypyrazol-1-yl)pyrimidine (9.5 g, 70%). 1H NMR (500MHz, chloroform-d) δppm 4.08 (s, 3H) 5.97 (d, J = 2.90Hz, 1H) 7.08 (t, J = 4.81Hz, 1H) 8.42 (d, J = 2.90Hz, 1H) 8.68 (d, J = 4.88Hz, 2H). LCMS:m / z:177[M+H]+

[0709] Step B: Preparation of 2-(5-iodo-3-methoxy-pyrazol-1-yl)pyrimidine

[0710] To a cooled solution (T < 0°C) of 2-(3-methoxypyrazol-1-yl)pyrimidine (7.5 g, 42.6 mmol, 1 eq) in tetrahydrofuran (113 mL) was added a 17 w / v% solution of 2,2,6,6-tetramethylpiperidinyl zinc chloride lithium complex in tetrahydrofuran (13.6 g, 79.9 mL, 17 w / v%, 47.9 mmol, 1.125 eq.) by maintaining the temperature T < 5°C. The reaction mixture was allowed to warm to room temperature and stirred for 6 hours. Thereafter, iodine (13.56 g, 53.43 mmol, 1.255 eq) was added at room temperature and the reaction was stirred at room temperature for 16 hours. After completion of the reaction, the reaction was cooled to 0°C, diluted with saturated aqueous ammonium chloride solution (200 mL), and extracted three times with ethyl acetate (3 × 200 mL). The combined organic layers were washed with saturated aqueous sodium bisulfite solution (200 mL) and saturated aqueous sodium chloride solution (100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure onto celite. The residue was purified by combi-flash chromatography eluting with a gradient of 60% to 100% ethyl acetate in hexanes to afford the desired product, 2-(5-iodo-3-methoxy-pyrazol-1-yl)pyrimidine (11.98 g, 93%). 1 H NMR (500 MHz, chloroform-d) δ ppm 4.06 (s, 3H) 6.28 (s, 1H) 7.25 (t, J = 1.00 Hz, 1H) 8.81 (d, J = 4.88 Hz, 2H). LCMS: m / z: 303 [M+H] +

[0711] Step C: Preparation of 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethanone

[0712] The flask equipped with 2-(5-iodo-3-methoxypyrazole-1-yl) pyrimidine (7.3g, 24.2mmol, 1eq) is evacuated and backfilled twice with nitrogen, then anhydrous toluene (28mL) is added via a syringe. The solution is degassed with nitrogen for 8-10 minutes, and then tributyl (1-ethoxy vinyl) stannane (9.601g, 8.981mL, 1.069g / mL, 26.6mmol, 1.1eq) and bis(triphenylphosphine) palladium dichloride (II) (1.696g, 2.42mmol, 0.1eq) are loaded. The reaction is refluxed at 92°C-95°C for 16 hours. The reaction is cooled to room temperature, and 2M aqueous hydrogen chloride solution (36mL) is loaded, and stirred for 2 hours. The reaction is diluted with ethyl acetate (200mL) and water (200mL). After separating each layer, the collected organic layer. The water layer is extracted three times with ethyl acetate (3×100mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered, and concentrated onto celite. The residue was purified by combi-flash chromatography using a gradient of 40% to 70% ethyl acetate in hexanes to afford the desired product, 1-(5-methoxy-2-pyrimidin-2-yl-pyrazole-3-yl)ethanone (1.62 g, 31%). 1 H NMR (500MHz, chloroform-d) δppm 2.52 (s, 3H) 4.07 (s, 3H) 6.20 (s, 1H) 7.21 (t, J = 4.88Hz, 1H) 8.73 (d, J = 4.88Hz, 2H). LCMS:m / z:219[M+H] +

[0713] Step D: N-[1-(5-Methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylidene]-2-methyl-propane-2-sulfenyl Preparation of amides

[0714] A mixture of 1-[5-methoxy-2-(pyrimidin-2-yl)pyrazol-3-yl]ethanone (1.88 g, 8.62 mmol, 1 eq) and tert-butylsulfonamide (1.149 g, 9.48 mmol, 1.1 eq) in anhydrous toluene (51 mL) was degassed with nitrogen for 5 minutes. To this solution was added titanium isopropoxide (4.897 g, 5.10 mL, 0.96 g / mL, 17.23 mmol, 2 eq) via syringe. The reaction mixture was refluxed at 105-110°C for 16 hours, then cooled to room temperature and quickly poured into a stirred saturated aqueous sodium chloride solution (100 mL). The reaction mixture was diluted with ethyl acetate (100 mL) and stirred for 10 minutes. The mixture was then filtered through a pad of celite, and the filter cake was subsequently washed with ethyl acetate (50 mL). The layers were separated, the organic layer collected, and the aqueous layer was extracted twice with ethyl acetate (2 x 50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated onto celite. The residue was purified by combi-flash chromatography eluting with a gradient of 0% to 100% ethyl acetate in hexanes to afford the desired product, N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylidene]-2-methyl-propane-2-sulfenamide, as an E and Z mixture (1.41 g, 51%). 1H NMR (500MHz, chloroform-d) δppm 1.19(s,27H)2.52(s,3H)2.63(s,6H)4.07(s,6H)4.08-4.09(m,3H)5.96- 6.04(m,1H)6.11(s,2H)7.08-7.14(m,1H)7.17(t,J=4.73Hz,2H)8.67(br d,J=4.12Hz,2H)8.72(d,J=4.73Hz,4H). LCMS:m / z:322[M+H] +

[0715] Step E: N-[1-(5-Methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-2-methyl-propane-2-sulfinyl Preparation of amines

[0716] At 0 ° C, sodium borohydride (0.285 g, 7.53 mmol, 2 eq) was added to a solution of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylidene]-2-methyl-propane-2-sulfinamide (1.21 g, 3.765 mmol, 1 eq) in methanol (75 mL) in batches. After gas evolution stopped, the reaction was warmed to room temperature and stirred for 2 hours. The reaction was cooled to 0 ° C and quenched with saturated ammonium chloride (100 mL). The solution was then concentrated under reduced pressure and the residue was distributed between water (100 mL) and ethyl acetate (100 mL). The organic layer was collected and the aqueous layer was washed twice with ethyl acetate (2 × 100 mL). The combined organic layers were washed with saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the product N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-2-methyl-propane-2-sulfenamide (1.22 g). The product was used in the next step without further purification. LCMS: m / z: 324 [M+H] +

[0717] Step F: Preparation of 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylammonium chloride

[0718] To a solution of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-2-methyl-propane-2-sulfinamide (128 mg, 0.396 mmol, 1 eq) prepared as in step E in 1,4-dioxane (0.64 mL) was added a solution of hydrogen chloride in dioxane (0.014 g, 0.099 mL, 4 M, 0.396 mmol, 1 eq) via syringe at 0°C. The reaction mixture was stirred at room temperature for an additional 30 minutes. The solid was collected by filtration and washed with dioxane (2-3 mL) and dried under reduced pressure to give the product, 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylammonium chloride (0.07 g, 69%). 1 H NMR(600MHz, DMSO-d6)δppm1.60(d,J=6.90Hz,3H)3.90(s,3H)5.19(dt,J=12.03,6.06Hz,1H)6.39(s,1H)7.46(t,J=4.81Hz,1H)8.48(br s,3H)8.86(d,J=4.90Hz,2H). LCMS:m / z:220[M+H] + (free amine).

[0719] Step G: N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzyl Preparation of amides

[0720] To a mixture of 1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethylammonium chloride (0.79 g, 3.089 mmol, 1 eq) and dichloromethane (25 mL) at 0°C was added 3,5-bis(trifluoromethyl)benzoyl chloride (1.28 g, 0.84 mL, 1.526 g / mL, 4.634 mmol, 1.5 eq), followed by the dropwise addition of triethylamine (0.938 g, 1.292 mL, 0.726 g / mL, 9.2 7 The mixture was stirred at 0 ° C for 10 minutes, and then allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was quenched with saturated sodium bicarbonate aqueous solution (100 mL) and extracted three times with dichloromethane (3 × 100 mL). The combined organic layer was dried over magnesium sulfate, filtered, and concentrated onto diatomaceous earth. The residue was purified by combi-flash chromatography using a gradient of 20%-60% ethyl acetate in hexane to obtain the desired product N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazole-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide, i.e., a compound of the present invention (0.90 g, 63%). 1 H NMR (500MHz, chloroform-d) δppm 1.56 (d, J = 7.02Hz, 3H) 4.06 (s, 3H) 5.98-6.06 (m, 1H) 6.07 (s, 1H) 7.24 (t, J = 1.00Hz, 1H) 8.01 (s, 1H) 8.22 (s, 2H) 8.46 (br d,J=7.93Hz,1H)8.80(d,J=4.88Hz,2H). LCMS:m / z:460[M+H] +

[0721] Step H: N-[1-(4-iodo-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)- Preparation of 4-(2-amino-4-methyl)benzamide

[0722] To a solution of N-[1-(5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (0.90 g, 1.96 mmol, 1 eq) in N,N-dimethylformamide (9 mL) was added N-iodosuccinimide (0.485 g, 2.16 mmol, 1.1 eq). The reaction mixture was heated to 80 ° C and stirred for 3 hours. The reaction mixture was cooled to room temperature and partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was collected and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were washed with saturated aqueous sodium bisulfite solution (100 mL), dried over magnesium sulfate, filtered, and concentrated onto celite. The residue was purified by combi-flash chromatography eluting with a gradient of 30% to 60% ethyl acetate in hexanes to give the desired product, N-[1-(4-iodo-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide, a compound of the present invention (0.82 g, 72%). 1 H NMR (500MHz, chloroform-d) δppm1.51 (d, J = 7.32Hz, 3H) 4.11 (s, 3H) 6.14-6.24 (m, 1H) 7.34(t,J=1.00Hz,1H)8.01(s,1H)8.29(s,2H)8.86(d,J=4.73Hz,2H)9.26(br d,J=8.54Hz,1H). LCMS:m / z:586[M+H] +

[0723] Step I Preparation of N-[1-(4-cyano-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide

[0724] Under nitrogen, in a microwave vial with a stir bar, N-[1-(4-iodo-5-methoxy-2-pyrimidin-2-yl-pyrazol-3-yl)ethyl]-3,5-bis(trifluoromethyl)benzamide (0.63 g, 1.08 mmol, 1 eq), zinc cyanide (0.506 g, 0.273 mL, 1.852 g / mL, 4.31 mmol, 4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.099 g, 0.108 mmol, 0.1 eq) and 1,1'-ferrocenediyl-bis(diphenylphosphine) (0.119 g, 0.215 mmol, 0.2 eq) and anhydrous N,N-dimethylformamide (6.3 mL) were added. The reaction mixture was irradiated under microwave at 120 ° C for 30 minutes. The reaction mixture was cooled to room temperature and partitioned between water (25 mL) and ethyl acetate (25 mL). At 4 DEG C, 1-dextrose is stirred 2 hours at 4 DEG C, 1-dextrose is stirred 1 hour at 4 DEG C, 1-dextrose is stirred 2 hours at 4 DEG C, 1-dextrose is stirred 3 hours at 4 DEG C, 1-dextrose is stirred 4 hours at 4 DEG C, 1-dextrose is stirred 3 ... 1 H NMR (500MHz, chloroform-d) δppm1.80 (d, J=7.02Hz, 3H) 4.13 (s, 3H) 6.41 (quin, J=7.17Hz, 1H) 7.35-7.40 (m, 1H) 7.43 (br d,J=7.17Hz,1H)8.03(s,1H)8.32(s,2H)8.90(d,J=4.88Hz,2H). LCMS:m / z:485[M+H] +

[0725] Synthesis Example 18

[0726] N-methyl-N-[1-[4-methylsulfonyl-2-[6-(trifluoromethyl)pyrimidin-4-yl]pyrazol-3-yl]ethyl]-3, 5-Bis(trifluoromethyl)benzamide (Compound 125)

[0727] Step A: Preparation of methyl 2-(methylamino)propionate hydrochloride

[0728] At 0 ° C, thionyl chloride (21 mL, 305 mmol) was slowly added to a stirred solution of 2-(methylamino)propionic acid (N-methyl-DL-alanine) (21 g, 203.6 mmol) in methanol (300 mL) cooled to 0 ° C under a nitrogen atmosphere. The mixture was stirred at 0 ° C for 15 minutes and then heated to reflux for 5 hours. The reaction mixture was concentrated under reduced pressure to obtain crude 2-(methylamino)methyl propionate hydrochloride (28 g, 90% yield) as an oily substance, which was used in the next step without purification.

[0729] 1 H NMR (500MHz, DMSO) δ9.63 (bs, NH), 9.29 (bs, NH), 4.11-4.08 (m, 1H), 3.76 (s, 3H), 2.56-2.51 (m, 3H), 1.48 (d, J = 7.0Hz, 3H)

[0730] Step B: Preparation of methyl 2-[[3,5-bis(trifluoromethyl)benzoyl]-methylamino]propionate

[0731] To a stirred solution of 3,5-bis(trifluoromethyl)benzoic acid (45 g, 0.174 mol) in dichloromethane (250 mL) was added dimethylformamide (1 mL), and oxalyl chloride (32.6 mL, 0.383 mol) was added dropwise under a nitrogen atmosphere at 0° C. The mixture was stirred at ambient temperature for 3 hours and then concentrated under reduced pressure to obtain the crude acid chloride.

[0732] In a separate dry round-bottom flask, 2-(methylamino) methyl propionate hydrochloride (obtained as above, 26.6g, 0.174mol) is dissolved in tetrahydrofuran (100mL), N, N-diisopropylethylamine (155mL, 0.87mol) is added, and a solution of the above-prepared acyl chloride in tetrahydrofuran (150mL) is added dropwise at 0°C. The mixture is heated to ambient temperature and stirred for 16 hours. The reaction mixture is poured into ice-cold water (300mL) and extracted with ethyl acetate (200mL×3). The combined organic phase is washed with water (100mL) and saturated sodium chloride aqueous solution (100mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue is subjected to flash column chromatography (0%-20% ethyl acetate in petroleum ether) to obtain 2-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino] methyl propionate (45g, yield 62%) as a yellow liquid.

[0733] LCMS (ESI) [M+H] + :358.17. 1H NMR (500MHz, CDCl3) δ7.94-7.91(m,3H),5.28-5.24(m,1H),3.79(s,3H),2.94(s,3H),1.56(d,3H)

[0734] Step C: N-methyl-N-(1-methyl-3-methylsulfonyl-2-oxo-propyl)-3,5-bis(trifluoromethyl)benzyl Preparation of amides

[0735] At 0 ° C under a nitrogen atmosphere, n-butyl lithium (2.5M in hexane, 38 mL, 95 mmol) was added to a stirred solution of dimethyl sulfone (9.85 g, 104.7 mmol) in tetrahydrofuran (220 mL) and stirred at 0 ° C for 20 minutes. This mixture was cooled to -78 ° C, and a solution of 2-[[3,5-bis(trifluoromethyl)benzoyl]-methyl-amino]propionic acid methyl ester (17 g, 47.6 mmol) in anhydrous tetrahydrofuran (50 mL) was added dropwise at -78 ° C, and it was slowly warmed to 0 ° C over 1 hour. The reaction mixture was poured into a cold 1N aqueous hydrogen chloride solution (300 mL) and extracted with ethyl acetate (200 mL × 3). The combined organic phase was washed with water (100 mL), a saturated sodium chloride aqueous solution (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to flash column chromatography (0%-50% ethyl acetate in petroleum ether) to obtain N-methyl-N-(4-(methylsulfonyl)-3-oxobutan-2-yl)-3,5-bis(trifluoromethyl)benzamide (18.5 g, 92% yield) as a white solid.

[0736] LCMS (ESI) [M+H] + :420.10 1 H NMR (400MHz, CDCl3) δ7.98(bs,1H),7.92(bs,2H),4.71(q,J=6.8Hz,1H),4.28-4.19(m,2H),3.12(s,3H),3.06(s,3H),1.56(d,J=7.2Hz,3H)

[0737] Step a: Preparation of [6-(trifluoromethyl)pyrimidin-4-yl]hydrazine

[0738] At 25 ℃, to a stirred solution of 4-chloro-6-(trifluoromethyl)pyrimidine (1g, 5.4mmol) in ethanol (10mL), hydrazine monohydrate (0.52mL, 10.8mmol) and triethylamine (0.83mL, 5.94mmol) were added. The reaction mixture was stirred at 100 ℃ for 5 hours and then concentrated under reduced pressure. The crude residue obtained was diluted with chloroform (20mL), filtered through diatomaceous earth, and concentrated to a solid. This solid was ground with ether (5mL) and n-pentane (10mL). The gained solid was vacuum dried to obtain the title substance (1g, crude product) as an off-white solid.

[0739] LCMS (ESI) [M+H] + :178.91. 1 H NMR(400MHz, CDCl3)δ8.64(s,1H),7.16(bs,1H),6.93(s,1H),3.94(bs,2H)

[0740] Steps D and E: N-methyl-N-[1-[4-methylsulfonyl-2-[6-(trifluoromethyl)pyrimidin-4-yl]pyrazole-3-yl]- Preparation of [3,5-bis(trifluoromethyl)benzamide]-1,2-difluoromethyl]ethyl

[0741] To a stirred solution of N-methyl-N-(4-(methylsulfonyl)-3-oxobutan-2-yl)-3,5-bis(trifluoromethyl)benzamide (500 mg, 1.19 mmol) in dichloromethane (10 mL) was added dimethylformamide dimethyl acetal (0.46 mL, 3.57 mmol) at ambient temperature under a nitrogen atmosphere. The reaction mixture was stirred at ambient temperature for 16 hours and then concentrated under reduced pressure to obtain a crude residue. This residue was dissolved in ethanol (5 mL), and acetic acid (1.5 mL) and [6-(trifluoromethyl)pyrimidin-4-yl]hydrazine (1 g, as obtained in step 1a above) were added, and the mixture was heated at 100 ° C for 4 hours. The reaction mixture was concentrated under reduced pressure, and the obtained crude material was treated with saturated aqueous sodium bicarbonate solution to neutral pH (30 mL), followed by extraction with dichloromethane (30 mL × 3). The combined organic phase was washed with water (30 mL) and saturated aqueous sodium chloride solution (30 mL), dried over sodium sulfate. The organic phase was concentrated under reduced pressure, and the residue was purified by column chromatography, eluted with 50% ethyl acetate in petroleum ether to obtain N-methyl-N-[1-[4-methylsulfonyl-2-[6-(trifluoromethyl)pyrimidin-4-yl]pyrazol-3-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide as a white solid, i.e., a compound of the present invention (300 mg, 42% yield).

[0742] LCMS (ESI) [M+H] + :590.19 1H NMR(400MHz, CDCl3)δ9.30(s,1H),8.32(s,1H),8.06(s,1H),7.88(bs,1H),7.67 (bs,2H),6.45(q,J=7.2Hz,1H),3.29(s,3H),3.20(s,3H),2.02(d,J=7.2Hz,3H)

[0743] The following compounds can be prepared by the procedures described herein and methods known in the art. The following abbreviations are used in the following tables: Me means methyl, Et means ethyl, i-Pr means isopropyl, i-Bu means isobutyl, c-Pr means cyclopropyl, and OMe means methoxy.

[0744] Table 1

[0745]

[0746] Q is Q-1, R 4 is CN, and R 5 It is NH2

[0747]

[0748]

[0749] In addition to R 4 Table 2 is the same as Table 1 except for NO2.

[0750] In addition to R 4 Except for Me, Table 3 is the same as Table 1.

[0751] In addition to R 5 Table 4 is the same as Tables 1 to 3 except that it is NHMe.

[0752] In addition to R 5 Table 5 is the same as Tables 1 to 3 except that OMe is used.

[0753] In addition to R 5 Table 6 is the same as Tables 1 to 3 except that it is SMe.

[0754] In addition to R 5 Except for C1, Table 7 is the same as Tables 1 to 3.

[0755] Table 8 is the same as Tables 1 to 7 except that Q is Q-2.

[0756] Table 9 is the same as Tables 1 to 7 except that Q is Q-3.

[0757] Table 10 is the same as Tables 1 to 7 except that Q is Q-4.

[0758] Table 11 is the same as Tables 1 to 7 except that Q is Q-5.

[0759] Table 12 is the same as Tables 1 to 7 except that Q is Q-6.

[0760] Table 13 is the same as Tables 1 to 7 except that Q is Q-7.

[0761] Table 14 is the same as Tables 1 to 7 except that Q is Q-8.

[0762] Table 15 is the same as Tables 1 to 7 except that Q is Q-9.

[0763] Table 16 is the same as Tables 1 to 7 except that Q is Q-10.

[0764] Table 17 is the same as Tables 1 to 7 except that Q is Q-11.

[0765] Table 18 is the same as Tables 1 to 7 except that Q is Q-12.

[0766] Table 19 is the same as Tables 1 to 7 except that Q is Q-13.

[0767] Table 20 is the same as Tables 1 to 7 except that Q is Q-14.

[0768] Table 21 is the same as Tables 1 to 7 except that Q is Q-15.

[0769] Table 22 is the same as Tables 1 to 7 except that Q is Q-16.

[0770] Table 23 is the same as Tables 1 to 7 except that Q is Q-17.

[0771] Table 24

[0772]

[0773] In addition to the title " Table 1 Table 24 is the same as Tables 1 to 23, except that the structure shown below is replaced by the structure shown above.

[0774] Table 25

[0775]

[0776] In addition to the title " Table 1 Table 25 is the same as Tables 1 to 23, except that the structure shown below is replaced by the structure shown above.

[0777] Table 26

[0778]

[0779] Q is Q-1, R 4 is CN, and R 5 Yes N H2

[0780]

[0781]

[0782] In addition to R 4 Table 27 is the same as Table 26 except for NO2.

[0783] In addition to R 4 Except for Me, Table 28 is the same as Table 26.

[0784] In addition to R 5 Table 29 is the same as Tables 26 to 28, except that it is NHMe.

[0785] In addition to R 5 Table 30 is the same as Tables 26 to 28 except for OMe.

[0786] In addition to R 5 Except for SMe, Table 31 is the same as Tables 26 to 28.

[0787] In addition to R 5 Except for C1, Table 32 is the same as Tables 26 to 28.

[0788] Table 33 is the same as Tables 26 to 32 except that Q is Q-2.

[0789] Table 34 is the same as Tables 26 to 32 except that Q is Q-3.

[0790] Table 35 is the same as Tables 26 to 32 except that Q is Q-4.

[0791] Table 36 is the same as Tables 26 to 32 except that Q is Q-5.

[0792] Table 37 is the same as Tables 26 to 32 except that Q is Q-6.

[0793] Table 38 is the same as Tables 26 to 32 except that Q is Q-7.

[0794] Table 39 is the same as Tables 26 to 32 except that Q is Q-8.

[0795] Table 40 is the same as Tables 26 to 32 except that Q is Q-9.

[0796] Table 41 is the same as Tables 26 to 32 except that Q is Q-10.

[0797] Table 42 is the same as Tables 26 to 32 except that Q is Q-11.

[0798] Table 43 is the same as Tables 26 to 32 except that Q is Q-12.

[0799] Table 44 is the same as Tables 26 to 32, except that Q is Q-13.

[0800] Table 45 is the same as Tables 26 to 32 except that Q is Q-14.

[0801] Table 46 is the same as Tables 26 to 32 except that Q is Q-15.

[0802] Table 47 is the same as Tables 26 to 32 except that Q is Q-16.

[0803] Table 48 is the same as Tables 26 to 32, except that Q is Q-17.

[0804] Table 49

[0805]

[0806] In addition to the title " Table 49 Table 49 is the same as Tables 26 to 48, except that the structure shown below is replaced by the structure shown above.

[0807] Table 50

[0808]

[0809] In addition to the title " Table 50 Table 50 is the same as Tables 26 to 48, except that the structure shown below is replaced by the structure shown above.

[0810] Specific compounds of Formula 1 prepared by the methods and variations described in Schemes 1-13 and Synthesis Examples 1-18 are shown in the Index Table below. The following abbreviations may be used: Cmpd means compound, t is tertiary, c is ring, Me is methyl, Et is ethyl, and Ph is phenyl. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which Synthesis Example the compound was prepared.

[0811] Melting point data (MP) are reported as temperature ranges (e.g., 122-126). Mass spectral data (MS) are reported as single values ​​(e.g., 542). + (M+1)), the reported values ​​are obtained by using atmospheric pressure chemical ionization (AP + ) by mass spectrometry and the M+1 peak observed by H + The molecular weight of the parent molecular ion (M) formed by adding the molecular weight to the molecule (molecular weight 1). Intervening molecular ion peaks (e.g., M+2 or M+4) that appear for compounds containing multiple halogens are not reported.

[0812] Index Table A

[0813]

[0814]

[0815]

[0816]

[0817]

[0818]

[0819] The compounds of the present invention will generally be used as invertebrate pest control active ingredients in compositions (i.e., formulations) having at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents acting as a carrier. These formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, the mode of application, and environmental factors such as soil type, moisture, and temperature.

[0820] Useful formulations include both liquid compositions and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates and / or suspoemulsions) that can optionally be thickened into gels. General types of aqueous liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, flowable concentrates and suspoemulsions. General types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates and oil dispersions.

[0821] The general types of solid compositions are dusts, powders, granules, pellets, granules, pastilles, tablets, filled films (including seed coatings), etc., which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed by film-forming solutions or flowable suspensions are particularly useful for seed treatment. The active ingredient can be (micro) encapsulated and further formed into a suspension or solid formulation; alternatively, the entire formulation of the active ingredient can be encapsulated (or "coated"). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of both emulsifiable concentrate formulations and dry granule formulations. High-strength compositions are primarily used as intermediates for other formulations.

[0822] Sprayable formulations are typically dispersed in suitable media before spraying. Such liquid and solid formulations are formulated into spray media, are generally water, but are occasionally another suitable medium that is easy to dilute as aromatic hydrocarbons or paraffin hydrocarbons or vegetable oils. The scope of spray capacity can be from about one liter to several thousand liters per hectare, but more typically is in the scope of about ten to several hundred liters per hectare. Sprayable formulations can be mixed with water or another suitable medium bucket, for applying by air or ground to carry out leaf treatment, or for being applied to the growth medium of plant. Liquid and dry formulations can be directly metered into the drip irrigation system, or are metered into the furrow during the planting period. Liquid and solid formulations can be applied to the seed of the vegetation of crops and other wishes as seed treatment agents before planting, to protect the root and other underground plant parts and / or leaves in the development by systemic absorption.

[0823] The formulation will typically contain effective amounts of active ingredient, diluent, and surfactant in an amount totaling up to 100 weight percent within the following approximate ranges.

[0824]

[0825] Solid diluents include, for example, clays (such as bentonite, montmorillonite, attapulgite, and kaolin), gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silicon dioxide, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd ed., Dorland Books, Caldwell, New Jersey.

[0826] Liquid diluents include, for example, water, N,N-dimethylalkaneamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oil, n-paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerol, triacetin, sorbitol, aromatic hydrocarbons, dearomatized aliphatic compounds, alkylbenzenes, alkylnaphthalenes, ketones (such as cyclohexanone, 2-heptanone, isophorone and 4-heptanone), The liquid diluents may also include saturated and unsaturated fatty acids (typically C6-C8). 22 ) glycerides of plant seed and fruit oils (e.g., olive oil, castor oil, linseed oil, sesame oil, corn oil (maize oil), peanut oil, sunflower oil, grapeseed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, coconut oil, and palm kernel oil), animal fats (e.g., tallow, lard, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated (e.g., methylated, ethylated, butylated) fatty acids, which can be obtained by hydrolysis of glycerides from plant and animal sources and purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd ed., Interscience, New York, 1950.

[0827] The solid and liquid compositions of the present invention typically contain one or more surfactants. When added to a liquid, a surfactant (also known as a "surface-active agent") typically alters, and most often reduces, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in the surfactant molecule, a surfactant can act as a wetting agent, dispersant, emulsifier, or defoaming agent.

[0828] Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants that can be used in the compositions of the present invention include, but are not limited to, alcohol alkoxylates, such as those based on natural and synthetic alcohols (which may be branched or linear) and prepared from alcohols and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof; amine ethoxylates, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, such as ethoxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxylates, such as octylphenol ethoxylate, nonylphenol ethoxylate, dinonylphenol ethoxylate, and dodecylphenol ethoxylate (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide, and trans block polymers in which the terminal blocks are prepared from propylene oxide; ethylene Oxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); fatty acid esters, glycerides, lanolin-based derivatives, polyethoxylated esters (such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitan fatty acid esters, and polyethoxylated glycerol fatty acid esters); other sorbitan derivatives, such as sorbitan esters; polymeric surfactants, such as random copolymers, block copolymers, alkyd PEG (polyethylene glycol) resins, graft or comb polymers, and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives, such as sucrose esters, alkyl polyglycosides, and alkyl polysaccharides.

[0829] Useful anionic surfactants include, but are not limited to, alkylarylsulfonic acids and salts thereof; carboxylated alcohol or alkylphenol ethoxylates; diphenylsulfonate derivatives; lignin and lignin derivatives, such as lignin sulfonates; maleic acid or succinic acid or their anhydrides; olefin sulfonates; phosphates, such as phosphates of alcohol alkoxylates, phosphates of alkylphenol alkoxylates, and phosphates of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfates; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides, such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecylbenzene and tridecylbenzene; sulfonates of polycondensed naphthalene; sulfonates of naphthalene and alkylnaphthalene; sulfonates of petroleum fractions; sulfosuccinamates; and sulfosuccinates and their derivatives, such as dialkylsulfosuccinates.

[0830] Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides; amines such as N-alkylpropylenediamine, tripropylenetriamine, and dipropylenetetramine, as well as ethoxylated amines, ethoxylated diamines, and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); amine salts such as ammonium acetate and diamine salts; quaternary ammonium salts such as quaternary ammonium salts, ethoxylated quaternary salts, and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

[0831] Also useful in the compositions of the present invention are mixtures of nonionic and anionic surfactants, or mixtures of nonionic and cationic surfactants. Nonionic, anionic, and cationic surfactants and their recommended uses are disclosed in a number of references, including McCutcheon's Emulsifiers and Detergents, annual American and International Editions, published by The Manufacturing Confectioner Publishing Co., McCutcheon's Division; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A.S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[0832] The compositions of the present invention may also contain formulation adjuvants and additives known to those skilled in the art as formulation aids (some of which may also be considered to function as solid diluents, liquid diluents, or surfactants). Such formulation adjuvants and additives can control: pH (buffers), foaming during processing (defoamers, such as polyorganosiloxanes), sedimentation of the active ingredient (suspending agents), viscosity (thixotropic thickeners), microbial growth in the container (antimicrobial agents), product freezing (antifreeze agents), color (dye / pigment dispersions), elution (film formers or stickers), evaporation (evaporation retardants), and other formulation properties. Film formers include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinyl pyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation excipients and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions, published by McCutcheon's Division of Manufacturing Confectioner Publishing Co., and PCT Publication WO 03 / 024222.

[0833] Typically, the compound of formula 1 and any other active ingredients are incorporated into the composition of the present invention by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions including emulsifiable concentrates can be prepared by simply mixing these ingredients. If the solvent of the liquid composition intended to be used as an emulsifiable concentrate is immiscible with water, an emulsifier is typically added to emulsify the solvent containing the active ingredient when diluted with water. Active ingredient slurries with a particle size of up to 2,000 μm can be wet-milled using a media mill to obtain particles with an average diameter of less than 3 μm. The aqueous slurry can be made into a finished suspension concentrate (see, for example, US3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations generally require a dry milling process to produce an average particle size in the range of 2 to 10 μm. Dusts and powders can be prepared by blending and typically by grinding (such as with a hammer mill or fluid energy mill). Granules and pellets can be prepared by spraying the active substance onto a preformed granule carrier or by agglomeration techniques. See, Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147-48; Perry's Chemical Engineer's Handbook, 4th edition, McGraw-Hill, New York, 1963, pp. 8-57 et seq., and WO 91 / 13546. Pellets can be prepared as described in US 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in US 4,144,050, US 3,920,442 and DE 3,246,493. Tablets may be prepared as taught in US 5,180,587, US 5,232,701 and US 5,208,030. Films may be prepared as taught in GB 2,095,558 and US 3,299,566.

[0834] For further information on the field of formulations, see "The Formulator's Toolbox - Product Forms for Modern Agriculture" in T. S. Woods, Pesticide Chemistry and Bioscience, The Food-Environment Challenge; T. Brooks and T. R. Roberts, eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, column 6, lines 16 to column 7, line 19, and Examples 10-41; U.S. Pat. No. 3,309,192, column 5, lines 43 to column 7, line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; U.S. Pat. No. 2,891,855, column 3, lines 66 to column 5, line 17, and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook, 8th ed., Blackwell Scientific Publications [Blackwell Scientific Publishers], Oxford, 1989; and Developments in formulation technology [Developments in formulation technology], PJB Publications [PJB Publishing Company], Richmond, UK, 2000.

[0835] In the following examples, all formulations were prepared in a conventional manner. Compound numbers refer to the compounds in Index Table A. Without further elaboration, it is believed that one skilled in the art can utilize the present invention to its fullest extent using the above description. Therefore, the following examples should be construed as merely illustrative and not limiting of this disclosure in any way. Unless otherwise indicated, percentages are by weight.

[0836] Example A

[0837] High-strength concentrate

[0838] Compound 1 98.5%

[0839] Silica aerogel 0.5%

[0840] Synthetic amorphous fine silica 1.0%

[0841] Example B

[0842] wettable powder

[0843]

[0844] Example C

[0845] Granules

[0846] Compound 8 10.0%

[0847] Attapulgite granules (low volatile matter, 0.71 / 0.30 mm; USS No. 25-50 sieve) 90.0%

[0849] Example D

[0850] Extruded pellets

[0851]

[0852] Example E

[0853] Emulsifiable concentrates

[0854] Compound 11 10.0%

[0855] Polyoxyethylene sorbitan hexaoleate 20.0%

[0856] C6-C 10 Fatty acid methyl esters 70.0%

[0857] Example F

[0858] microemulsion

[0859]

[0860] Example G

[0861] Seed treatment agents

[0862]

[0863] Example H

[0864] Fertilizer sticks

[0865]

[0866]

[0867] Example I

[0868] Suspension concentrates

[0869]

[0870] Example J

[0871] Emulsion in water

[0872]

[0873] Example K

[0874] oil dispersion

[0875]

[0876] Example L

[0877] suspension

[0878]

[0879] Example M

[0880] Suspension concentrates

[0881]

[0882] Instance N

[0883] Emulsion in water

[0884]

[0885] Example O

[0886] oil dispersion

[0887]

[0888] Instance P

[0889] suspension

[0890]

[0891]

[0892] Compound of the present invention shows the activity for the invertebrate harmful organism of wide spectrum.These harmful organisms comprise the invertebrates that inhabit in various environments, and these environments are for example like the crop or other food or building structure of the leaf, root, soil, harvest of plant.These harmful organisms comprise for example with leaf (comprising leaf, stem, flower and fruit), seed, timber or textile fiber for food and therefore for example growing or storing agronomy crop, forest, greenhouse crop, ornamental plant, nursery crop, stored food and fiber product or house or other structure or its content the invertebrates that causes harm or damage.It will be appreciated by those skilled in the art that not all compounds are equally effective to all growth stages of all harmful organisms.

[0893] Therefore, these compounds of the present invention and composition can be used for protecting field crops from the infringement of herbivorous invertebrate harmful organisms in agronomy, and can also be used for protecting other horticultural crops and plants from the infringement of herbivorous invertebrate harmful organisms in non-agronomy.This effectiveness includes protecting crops and other plants (i.e., agronomy and non-agronomy) containing the genetic material introduced by genetic engineering (i.e., transgenic) or modified by mutagenesis, to provide favorable traits. The example of this type of proterties includes tolerance to herbicides, resistance to herbivorous harmful organisms (e.g., insects, mites, aphids, spiders, nematodes, snails, plant pathogenic fungi, bacteria and viruses), plant growth is improved, tolerance to adverse growth conditions (such as high temperature or low temperature, low soil moisture or high soil moisture and high salinity) is increased, flowering or results are increased, harvest yield is larger, maturity is faster, the quality and / or nutritional value of harvest products are higher or the storage or processing characteristics of harvest products are improved. Transgenic plants can be modified to express multiple traits. Examples of plants containing traits provided by genetic engineering or mutagenesis include corn, cotton, soybean, and potato varieties expressing Bacillus thuringiensis insecticidal toxins, such as YIELD and INVICTA RR2PRO TM , and herbicide-tolerant corn, cotton, soybean, and rapeseed varieties, such as ROUNDUP LIBERTY and The present invention also provides a method for producing crops that are resistant to glyphosate herbicides or crops that contain HRA genes that provide resistance to the herbicides that inhibit acetolactate synthase (ALS). The compounds and compositions of the present invention can show an enhancement effect of traits introduced by genetic engineering or modified by mutagenesis, thereby enhancing the phenotypic expression or effectiveness of traits, or increase the invertebrate pest control effectiveness of the compounds and compositions of the present invention. In particular, the compounds and compositions of the present invention can show an enhancement effect of the phenotypic expression of proteins or other natural products that are toxic to invertebrate pests, to provide greater than additive control of these harmful organisms.

[0894] Composition of the present invention can also optionally comprise plant nutrients, for example, fertilizer composition, this fertilizer composition comprises at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulphur, calcium, magnesium, iron, copper, boron, manganese, zinc and molybdenum.It should be noted that the composition comprising at least one fertilizer composition, this at least one fertilizer composition comprises at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulphur, calcium and magnesium.The present composition further comprising at least one plant nutrient can be in liquid or solid form.It should be noted that the solid formulation in the form of granule, stick or tablet.Can be by compound of the present invention or composition and fertilizer composition and formulation ingredients are mixed, and then prepare the solid formulation comprising fertilizer composition by the method such as granulation or extrusion preparation preparation.Alternately, can be by compound of the present invention or composition solution in volatile solvent or suspension sprayed on the fertilizer composition in the form of dimensionally stable mixture (for example, granule, stick or tablet) previously prepared, and then solvent evaporation prepares solid formulation.

[0895] Non-agricultural uses refer to invertebrate pest control in areas outside of crop plant fields. The non-agricultural uses of the compounds and compositions of the present invention include invertebrate pest control in stored grains, beans and other foods and textiles such as clothes and carpets. The non-agricultural uses of the compounds and compositions of the present invention also include invertebrate pest control in ornamental plants, forests, gardens, roadsides and railroad lands and turf such as lawns, golf courses and pastures. The non-agricultural uses of the compounds and compositions of the present invention also include invertebrate pest control in houses and other buildings that may be occupied by humans and / or companion animals, farm animals, ranch animals, zoo animals or other animals. The non-agricultural uses of the compounds and compositions of the present invention also include the control of pests such as termites that may damage the wood or other structural materials used in buildings.

[0896] Examples of agronomic or non-agronomic invertebrate pests include eggs, larvae and adults of the order Lepidoptera, such as armyworms, cutworms, loopers and heliothines of the family Noctuidae (e.g., pink stem borer (Sesamia inferens Walker), corn stalk borer (Sesamia nonagrioides Lefebvre), southern armyworm (Spodoptera eridania Cramer), fall armyworm (Spodoptera frugiperda JESmith), beet armyworm (Spodoptera exigua Hübner), cotton leafworm (Spodoptera spp. littoralis Boisduval), yellowstriped armyworm (Spodoptera ornithogalli Guenée), black cutworm (Agrotis ipsilon Hufnagel), velvet bean caterpillar (Anticarsia gemmatalis Hübner), green fruitworm (Lithophane antennata Walker), cabbage armyworm (Barathra brassicae Linnaeus), soybean looper (Pseudoplusia includens Walker), cabbage looper (Trichoplusia ni Hübner), tobacco budworm (Heliothis virescens Fabricius); borers, casebearers, webworms, coneworms, cabbageworms, and skeletonizers from the family Pyralidae (e.g., European corn borer,

[0013] The present invention also includes the following:

[0013] Ostrinia nubilalis Hübner, navel orangeworm (Amyelois transitella Walker), corn root webworm (Crambus caliginosellus Clemens), sod webworms (Crambinae), such as sod worm (Herpetogramma licarsisalis Walker), sugarcane stem borer (Chilo infuscatellus Snellen), tomato small borer (Neoleucinodeselegantalis Guenée), green leafroller (Cnaphalocrocism medinalis), grape leafroller (Cnaphalocrocism medinalis), and worms. leaffolder (grape borer (Desmia funeralis Hübner)), melon worm (cucumber silk borer (Diaphania nitidalis Stoll)), cabbage center grub (Helluala hydralis Guenée), yellow stem borer (Scirpophaga incertulas Walker), early shoot borer (Sugarcane borer (Scirpophaga infuscatellus Snellen)), white stem borer (Scirpophaga innotata Walker), top shoot borer (Sugarcane white borer (Scirpophaga nivella Fabricius)), dark-headed rice borer (Chilo polychrysus Meyrick), striped rice borer (Chilo suppressalis Walker), cabbagecluster caterpillar,Crocidolomia binotalis English); leafrollers, budworms, seed worms, and fruit worms of the family Tortricidae (e.g., codling moth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteana Clemens), oriental fruit moth (Grapholita molesta Busck), citrus false codling moth (Cryptophlebia leucotreta Meyrick), citrus borer (Ecdytolophaaurantiana Lima), redbanded leafroller (Argyrotaenia velutinana Walker), obliquebanded leafroller (Choristoneura rosaceana and many other economically important Lepidoptera (e.g., diamondback moth, Plutella xylostella Linnaeus), pink bollworm,Pectinophora gossypiella Saunders), gypsy moth (Lymantriadispar Linnaeus), peach fruit borer (Carposina niponensis Walsingham), peach twig borer (Anarsia lineatella Zeller), potato tuberworm (Phthorimaea operculella Zeller), spotted teniform leafminer (Lithocolletis blancardella Fabricius), Asiatic apple leafminer (Lithocolletis ringoniella Matsumura), rice leaffolder (Lerodea eufala Edwards), apple leafminer (Leucoptera scitella Zeller))); eggs, nymphs, and adults of the order Blattellidae, including cockroaches from the families Blattellidae and Blattidae (e.g.,Oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella germanica Linnaeus), brownbanded cockroach (Supella longipalpa Fabricius), American cockroach (Periplaneta americana Linnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeira cockroach (Leucophaea maderae Fabricius), smoky brown cockroach (Periplaneta fuliginosa Service), Australian Cockroach (Periplaneta australasiae Fabr.), lobster cockroach (Nauphoeta cinerea Olivier), and smooth cockroach (Symploce pallens Stephens); eggs, leaf-feeding, fruit-feeding, root-feeding, seed-feeding, and vesicle-feeding larvae and adults of the order Coleoptera, including weevils from the families Anthribidae, Bruchidae, and Curculionidae (e.g., boll weevil (Anthonomus grandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granary weevil (Sitophilus spp.), and larvae of the family Sphaeroides. granariusLinnaeus), rice elephant (rice weevil,and leafminers (e.g., Colorado potato beetle (Leptinotarsa ​​decemlineata Say), western corn rootworm (Diabrotica spp.), flea beetles, cucumber beetles, rootworms, leaf beetles, potato beetles, and leafminers (e.g., Colorado potato beetle (Leptinotarsa ​​decemlineata Say), western corn rootworm (Diabrotica spp.). virgifera virgifera LeConte); scarab beetles and other beetles from the family Scarabaeidae (e.g., Japanese beetle (Popillia japonica Newman), oriental beetle (Popillia japonicaAnomala orientalis Waterhouse, Exomala orientalis (Waterhouse) Baraud), northern masked chafer (Cyclocephala borealis Arrow), southern masked chafer (Cyclocephala immaculata Olivier or C. lurida Bland), dung beetles and white grubs (Aphodius species), black turfgrass ataenius (Ataenius spretulus Haldeman), green June beetle (Cotinis nitida Linnaeus), Asiatic garden beetle (Maladera castanea Arrow), May / June gill beetle (Aphodius spp.), black turfgrass ataenius (Ataenius spretulus Haldeman), green June beetle (Cotinis nitida Linnaeus), Asian garden beetle (Maladera castanea Arrow), May / June gill beetle (Aphodius spp.), black turfgrass ataenius (Ataenius spretulus Haldeman), green June beetle (Cotinis nitida Linnaeus), Asian garden beetle (Maladera castanea Arrow), May / June gill beetle (Aphodius spp.), black turfgrass ataenius (Ataenius spretulus Haldeman), green June beetle (Cotinis nitida Linnaeus), Asian garden beetle (Maladera castanea Arrow), May / June gill beetle (Aphodius spp.), black turfgrass ataenius (Ataenius spretulus Haldeman), green June beetle (Cotinis nitida Linnaeus), Asian garden beetle (Ataenius spp.), beetles (Phyllophaga species) and European chafer (Rhizotrogus majalis Razoumowsky); carpet beetles from the Dermestidae family; wireworms from the Elateridae family; bark beetles from the Scolytidae family and flour beetles from the Tenebrionidae family.

[0897] In addition, agronomic and non-agronomic pests include: eggs, adults and larvae of the order Dermoptera, including earwigs from the family Forficulidae (e.g., European earwig (Forficulaauricularia Linnaeus), black earwig (Chelsoches morio Fabricius));Eggs, larvae, adults and nymphs of the orders Hemiptera and Homoptera, such as plant bugs from the family Miridae, cicadas from the family Cicadidae, leafhoppers from the family Cicadellidae (e.g., Empoasca species), bed bugs from the family Cimicidae (e.g., Cimex lectularius Linnaeus), planthoppers from the superfamily Fulgoroidae and the family Delphacidae, treehoppers from the family Membracidae, psyllids from the family Psyllidae, whiteflies from the family Aleyrodidae, aphids from the family Aphididae, phylloxera from the family Phylloxeridae, mealybugs from the family Pseudococcidae, scales from the families Coccidae, Diaspididae, and Margarodidae, lace bugs from the family Tingidae, stink bugs from the family Pentatomidae, bugs), chinch bugs from the Lygaeidae family (e.g., Blissus leucopterus hirtus Montandon and Blissus insularis Barber), and other seed bugs from the Lygaeidae family, spittlebugs from the Cercopidae family, squash bugs from the Coreidae family, and red bugs and cotton stainers from the Pyrrhocoridae family.

[0898] Agronomic and non-agronomic pests also include: eggs, larvae, nymphs and adults of the order Acari (Mites), such as spider mites and red mites of the family Tetranychidae (e.g., Panonychus ulmi Koch, Tetranychus urticae Koch, Tetranychus mcdanieli McGregor); flat mites of the family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisi McGregor)); rust mites and bud mites of the family Eriophyidae. mite and other leaf-feeding mites, dust mites of the family Epidermoptidae, follicle mites of the family Demodicidae, grain mites of the family Glycyphagidae; ticks of the family Ixodidae, commonly known as hard ticks (e.g., the deer tick (Ixodes capularis Say), the Australian paralysis tick (Ixodes holocyclus Neumann), the American dog tick (Dermacentor variabilis Say), the lone star tick (Amblyomma americanum Linnaeus)) and ticks of the family Argasidae, commonly known as soft ticks (e.g., the relapsing fever tick (Ornithodoros turicata), the common fowl tick (Argas radiatus); scab mites and itch mites of the families Psoroptidae, Pyemotidae, and Sarcoptidae; eggs, adults, and larvae of Orthoptera, including grasshoppers, locusts, and crickets (e.g., migratory grasshoppers (e.g., Melanoplus sanguinipes Fabricius), M.differentialis Thomas), American grasshoppers (e.g., American desert locust (Schistocerca americana Drury), desert locust (Schistocerca gregaria Forskal), migratory locust (Locusta migratoria Linnaeus), bush locust (Zonocerus species), house cricket (Acheta domesticus Linnaeus), mole crickets (e.g., tawny molecricket (Scapteriscus vicinus Scudder) and southern mole cricket (Scapteriscus borellii Giglio-Tos)); eggs, adults, and larvae of Diptera, including leaf miners (e.g., Liriomyza species, such as serpentine vegetable mole cricket leafminer (Liriomyza sativae Blanchard), midges, fruit flies (Tephritidae), frit flies (e.g., Oscinella frit Linnaeus), soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser house flies (e.g., Fannia canicularis Linnaeus), small house flies (F.femoralis Stein), stable flies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blow flies (e.g., Chrysomya species, Phormia species) and other muscoid fly pests, horse flies (e.g., Tabanus species), bot flies (e.g., Gastrophilus species, Oestrus species), cattle grubs (e.g., Hypoderma species), deer flies (e.g., Chrysops species), keds (e.g., Melophagus ovinus Linnaeus) and other Brachycera, mosquitoes (e.g., Aedes species, Anopheles species, Culex species), black flies (e.g., Prosimulium species, Simulium species), biting midges, sand flies, sciarids, and other Nematocera; eggs, adults, and larvae of the order Thysanoptera, including onion thrips (Thrips tabaci Lindeman), flower thrips (Frankliniella species), and other leaf-feeding thrips; insect pests of the order Hymenoptera, including ants of the family Formicidae, including the Florida carpenter ant (Camponotus floridanus Buckley), red carpenter ant (Camponotusferrugineus Fabricius), black carpenter ant (Camponotus pennsylvanicusDe Geer), white-footed ant (Technomyrmex albipes fr.Smith), big-headed ants (Pheidole species), ghost ants (Tapinomamelanocephalum Fabricius); Pharaoh ants (Monomorium pharaonis Linnaeus), little fire ants (Wasmannia auropunctata Roger), fire ants (Solenopsis geminata Fabricius), red imported fire ants (Solenopsis invicta Buren), Argentine ants (Iridomyrmex humilis Mayr), crazy ants (Paratrechina longicornis Latreille), pavement ants (Tetramorium caespitum Linnaeus), cornfield ants (Lasius alienus). ) and odorous house ant (Tapinoma sessile Say). Other Hymenoptera, including bees (including carpenter bees), hornets, yellow jackets, wasps, and sawflies (Neodiprion species; Cephus species); insect pests of the Isoptera, including termites of the families Termitidae (e.g., Macrotermes species, Odontotermes obesus Rambur), Kalotermitidae (e.g., Cryptotermes species), and Rhinotermitidae (e.g., Reticulitermes species, Coptotermes species, Heterotermes tenuis Hagen), eastern subterranean termites (Reticulitermes flavipes), and genus Coptotermes. Kollar), western subterranean termite (Reticulitermes hesperus Bank), Formosan white termite (Coptotermes formosanus Shiraki), West Indian drywood termite (Incisitermes immigrans Snyder), powdery termite (Cryptotermes brevis Walker), drywood termite (Incisitermes snyderi Light), southeastern subterranean termite (Reticulitermes virginicus Banks), western drywood termite (Incisitermes minor Hagen), arboreal termites such as species of the genus Nasutitermes, and other economically important termites; insect pests of the order Thysanura, such as silverfish (Lepisma saccharina Linnaeus) and firebrat (Thermobia domestica Packard).Additional arthropod pests covered include spiders of the order Araneae, such as the brown recluse spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes of the order Scolopendra, such as the house centipede (Scutigera coleoptrata Linnaeus).

[0899] Examples of invertebrate pests of stored grain include the larger grain borer (Prostephanus truncatus), the lesser grain borer (Rhyzopertha dominica), the rice weevil (Stiophilus oryzae), the maize weevil (Stiophilus zeamais), the cowpea weevil (Callosobruchus maculatus), the red flourbeetle (Tribolium castaneum), the granary weevil (Stiophilus granarius), the Indian meal moth (Plodia interpunctella), the Mediterranean flourbeetle (Ephestia kuhniella), and the flat or rusty grain beetle (Ephestia kuhniella). beetle)(Cryptolestis ferrugineus).

[0900] The compounds of the present invention are active against pests in the order Lepidoptera (e.g., Alabama argillacea Hübner (cotton leafworm), Archips argyrospila Walker (fruit leaf roller), A.rosana Linnaeus (European leaf roller), and other Archips species, Chilo suppressalis Walker (rice borer), Cnaphalocrosis medinalis Guenée (rice leaf roller), Crambus caliginosellus Clemens (corn root webworm), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (spiny stem borer), Earias vittella Fabricius (spotted stem borer), Helicoverpa armigera Hübner (American bollworm), Helicoverpa zea Corn earworm (Corn boddie), Heliothis virescens Fabricius (Tobacco budworm), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis & Schiffermüller (Grape leafroller), Pectinophoragossypiella Saunders (pink bollworm), Phyllocnistis citrella Stainton (citrus leafminer), Pieris brassicae Linnaeus (Large white cabbage butterfly), Pieris rapae Linnaeus (Small white cabbage butterfly), Plutella xylostella Linnaeus (diamondback moth), Spodoptera exigua Hübner (beet armyworm), Spodoptera litura Fabricius (tobacco cutworm, cluster moth) caterpillar), Spodoptera frugiperda JESmith (Fall Armyworm), Trichoplusia ni Hübner (cabbage looper), and Tuta absoluta Meyrick (tomato leafminer).

[0901] The compounds of the present invention are active against pests of the order Homoptera, including: Acyrthosiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid), Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer (apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthumsolani Kaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell (strawberry aphid), Diuraphis noxia (wheat aphid), and Aphis serrata (sweet aphid). Kurdjumov / Mordvilko (Russian wheat aphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosoma lanigerum Hausmann (wooly apple aphid), Hyalopterus pruni Geoffroy (mealy plum aphid), Lipaphis erysimi Kaltenbach (turnip aphid), Metopolophium dirrhodum Walker (cereal aphid), Macrosiphum euphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach-potato aphid), Nasonovia ribisnigri Mosley (lettuce aphid) aphid), Pemphigus species (root aphids and gallaphids), corn aphid (Rhopalosiphum maidis Fitch,corn leaf aphid), Rhopalosiphum padi Linnaeus (bird cherry-oat aphid), Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius (English grain aphid), Therioaphis maculata Buckton (spotted alfalfa aphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid), and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges species (adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly); whitefly), sweet potato whitefly), Bemisia argentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citri Ashmead (citrus whitefly), and Trialeurodes vaporariorum Westwood (greenhouse whitefly); Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigropictus (two-spotted black leafhopper), Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigropictus (two-spotted black leafhopper), Empoasca fabae Harris (potato leafhopper), Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestes quadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler (green leafhopper), Nephotettix nigropictus (two-spotted black leafhopper), ) (rice leafhopper), brown planthopper (Nilaparvata lugens brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatellafurcifera Horvath (white-backed planthopper), Sogatodes orizicola Muir (rice delphacid), Typhlocyba pomaria McAtee (white apple leafhopper), Erythroneoura species (grape leafhoppers); Magicidada septendecim Linnaeus (periodical cicada); Icerya purchasi Maskell (cottony cushion scale), Quadraspidiotus perniciosus Comstock (San Jose scale); Planococcus citri Risso (citrus mealybug). mealybug); Pseudococcus species (other mealybug groups); pear psylla (Cacopsyllapyricola Foerster), persimmon psylla (Trioza diospyri Ashmead).

[0902] The compounds of the present invention have activity against Hemiptera pests, including: green rice stink bug (Acrosternum hilareSay), pumpkin stink bug (Anasa tristis De Geer), wheat stink bug (Blissus leucopterus leucopterusSay), temperate zone stink bug (Cimex lectularius Linnaeus), cotton net stink bug (Corythuca gossypiiFabricius), tomato stink bug (Cyrtopeltis modesta Distant), cotton red stink bug (Dysdercus suturellus Herrich- ), brown stink bug (Euchistus servus Say), single-spotted stink bug (Euchistus variolarius Palisot de Beauvois), Graptosthetus species (long stink bug group), brown winged stink bug (Halymorpha halys ), Pine root stink bug (Leptoglossus corculus Say), American pasture blind bug (Lygus lineolaris Palisot de Beauvois), Southern green stink bug (Nezara viridula Linnaeus), Rice brown stink bug (Oebalus pugnax Fabricius), Giant milkweed stink bug (Oncopeltus fasciatus Dallas), Cotton blind bug (Pseudatomoscelisseriatus Reuter). Other insect orders controlled by the compounds of the present invention include Thysanoptera (e.g., Frankliniella occidentalis Pergande, Scirthothrips citri Moulton, Sericothrips variabilis Beach, and Onion Thrips; and Coleoptera (e.g., Colorado potato beetle, Epilachna varivestis Mulsant, Mexican bean beetle, and wireworms of the genera Agriotes, Athous, or Limonius).

[0903] Of note is the use of the compounds of the present invention for controlling and combating the diamondback moth (Plutella xylostella). Of note is the use of the compounds of the present invention for controlling and combating the fall armyworm (Spodoptera frugiperda). Of note is the use of the compounds of the present invention for controlling and combating the western flower thrips (Frankliniella occidentalis). Of note is the use of the compounds of the present invention for controlling and combating the potato leafhopper (Empoasca fabae). Of note is the use of the compounds of the present invention in controlling and combating the corn planthopper (Cephalopoda zeae). Of note is the use of the compounds of the present invention for controlling and combating the melon aphid (Aphis gossypii). Of note is the use of the compounds of the present invention for controlling and combating the peach aphid (Myzus persicae). Of note is the use of the compounds of the present invention for controlling and combating the sweet potato whitefly (Bemisia tabaci).

[0904] The compound of the present invention can also be used to increase the vigor of crop plants.This method includes making crop plants (for example, leaf, flower, fruit or root) or the seed of growing crop plants contact with the compound of formula 1 enough to realize the amount (i.e. biologically effective amount) of the plant vigor effect of hope.Typically, the compound of formula 1 is applied with the composition of preparation.Although there is the compound of formula 1 usually directly applied to crop plants or their seeds, these compounds can also be applied to the location of crop plants, i.e. the environment of crop plants, particularly close enough to allow the compound with formula 1 to migrate to the environmental part of crop plants.The location related to this method most commonly includes growth medium (i.e. providing a medium for nutrients to plant), typically the soil of plant growth.Therefore, in order to increase the vigor of crop plants, the processing of crop plants includes making crop plants, growing the seed of crop plants or the location of crop plants contact with the compound with formula 1 of biologically effective amount.

[0905] Increasing crop vigor can result in one or more of the following observed effects: (a) optimal crop establishment as demonstrated by superior seed germination, crop emergence, and crop stand; (b) enhanced crop growth as demonstrated by rapid and robust leaf growth (e.g., as measured by leaf area index), plant height, tiller number (e.g., for rice), root mass, and total dry weight of the vegetative body of the crop; (c) improved crop yield as demonstrated by time to flowering, duration of flowering, number of flowers, total biomass accumulation (i.e., yield), and / or product grade marketability of fruit or grain (i.e., yield quality); (d) enhanced ability of crops to tolerate or prevent infection by plant diseases and attack by arthropod, nematode, or mollusk pests; and (e) increased ability of crops to tolerate environmental stresses, such as exposure to extreme heat, suboptimal moisture, or phytotoxic chemicals.

[0906] Compared to untreated plants, the compounds of the present invention can increase the vitality of treated plants by killing phytophagous invertebrate pests or otherwise preventing phytophagous invertebrate pests from feeding in the plant environment. In the absence of such control of phytophagous invertebrate pests, pests reduce plant vitality by consuming plant tissues or juices, or spreading plant pathogens such as viruses. Even in the absence of phytophagous invertebrate pests, the compounds of the present invention can increase plant vitality by changing the metabolism of the plants. Generally, if the plant is grown in a non-ideal environment, that is, an environment that contains one or more aspects that are not conducive to the plant achieving its full genetic potential that should be displayed in an ideal environment, the vitality of the crop plant will be most significantly increased by treating the plant with the compounds of the present invention.

[0907] It should be noted that the method for increasing crop plant vigor, wherein the crop plant grows in the environment comprising a phytophagous invertebrate pest. It should also be noted that the method for increasing crop plant vigor, wherein the crop plant grows in the environment not comprising a phytophagous invertebrate pest. It should also be noted that the method for increasing crop plant vigor, wherein the crop plant grows in the environment comprising a moisture content that is less than the ideal moisture content for supporting crop plant growth. It should be noted that the method for increasing crop plant vigor, wherein the crop is rice. It should also be noted that the method for increasing crop plant vigor, wherein the crop is maize (corn). It should also be noted that the method for increasing crop plant vigor, wherein the crop is soybean.

[0908] The compounds of the present invention may also be mixed with one or more other biologically active compounds or agents to form multi-component pesticides, thereby imparting an even broader spectrum of agronomic and non-agronomic effects, including insecticides, fungicides, nematicides, bactericides, acaricides, herbicides, herbicide safeners, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, viruses or fungi. Therefore, the present invention also relates to a composition comprising a biologically effective amount of a compound having formula 1, at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, and at least one additional biologically active compound or agent. For the mixtures of the present invention, the other biologically active compounds or agents can be formulated together with the compounds of the present invention (including compounds having Formula 1) to form a premix, or the other biologically active compounds or agents can be formulated separately from the compounds of the present invention (including compounds having Formula 1) and the two formulations combined together (e.g., in a spray tank) before application, or alternatively, the two formulations can be applied sequentially.

[0909] Examples of such biologically active compounds or agents that can be formulated with the compounds of the present invention are insecticides such as abamectin, acephate, acetamiprid, acetofluthrin, bifenthrin ([(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methylcyclopropanecarboxylate) , sulfamethoxam, amitraz, avermectin, azadirachtin, azophos, benfuracarb, sulfanilamide, bifenthrin, bifenazate, bistrifluan, borate, buprofezin, cadusafos, carbaryl, carbofuran, cartap, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorpyrifos, methyl chlorpyrifos, cyclofenazol, clofentazine, clothianidin, cyanantraniliprole (3-bromo-1-(3-chloro-2-pyridyl)-N-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide), cyclobromoantraniliprole (3-bromo-N-[2-bromo-4-chloro-6-[[(1-cyclopropylethyl)amino]carbonyl]phenyl]-1- (3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide), cypermethrin, cycloheximide ((5S,8R)-1-[(6-chloro-3-pyridyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-5,8-epoxy-1H-imidazo[1,2-a]azepine), cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, beta-cyhalothrin, beta-cyhalothrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, tetrafluthrin, dimethoate, dinotefuran, benzylpezil, emamectin, endosulfan, high cyanamide Valerianthrin, ethomethrin, ethomethrin, etoxazole, fenbutatin, fenitrothion, fenthiocarb, fenoxycarb, cypermethrin, cypermethrin, fipronil, flumetolquinone (2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]-4-quinolylmethyl carbonate), flonicamid, flubendiamide, flucythrin, flufenoxuron, flutolan ((αE)-2-[[2-chloro-4-(trifluoromethyl)phenoxy]methyl]-α-(methoxymethylene)phenylacetic acid methyl ester), diflunisal (5-chloro-2-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]thiazole), fluhexenic acid, fluopyram, butyronitrile (1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methyl-2-propen-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile), flupyrone (4-[[(6-chloro-3-pyridyl)methyl](2,2-difluoroethyl)amino]-2(5H)-furanone), fluvalinate, fluvalinate, flufenacet, flufenacet, flufenoxam, thiamethoxam, chlorfenapyr, tebufenoxate ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-[(1Z)-3,3,3-trifluoro- -1-propylene-1-yl] cyclopropanecarboxylate), hexaflumuron, hexathiazox, hydrazone, imidacloprid, indoxacarb, insecticidal soap, isopropylamine, lufenuron, malathion, chlorflumethrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1R,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate), metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, metofluthrin, methoxyfenozide, metofluthrin, monocrotophos, monofluthrin ([2,3,5,6-tetrafluoro-4 -(methoxymethyl)phenyl]methyl 3-(2-cyano-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate), nicotine, nitenpyram, nithiazine, fluazifop, noviflumuron, oxamyl, parathion, methyl parathion, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargyl, propanthrin, pyrimethrin, 1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]- 1H-pyrazole-4-carboxamide), pymetrozine, pyraclostrobin, pyrethrin, pyridabenzan, pyridalyl, pyrimethrin, pyrimidine, pyrimidine, pyrimidine ((αE)-2-[[[2-[(2,4-dichlorophenyl)amino]-6-(trifluoromethyl)-4-pyrimidinyl]oxy]methyl]-α-(methoxymethylene)phenylacetic acid methyl ester), pyraclostrobin, pyriproxyfen, rotenone, ryanodine, silafluanid, ethyl spinosad, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor (N-[methyloxide [1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-λ, 4[-sulfenylamino]cyanamide), tebufenozide, tebufenpyrad, flubendiamide, tefluthrin, terbufos, chlorpyrifos, tetrathrin, tetrafluthrin ([2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2,3,3-tetramethylcyclopropanecarboxylate), tetrafluanid, thiacloprid, thiomethoxam, thiodicarb, dimethoate, thiazoxafin (3-phenyl-5-(2-thienyl)-1,2,4-oxadiazole), tolfenpyrad, tralomethrin, triazolam, trichlorfon, triflumuron (2,4-dioxo-1-(5-pyrimidinylmethyl)-3-[3-(trifluoromethyl)phenyl]-2H-pyrido[1,2-a]pyrimidine inner salt), triflumuron, Bacillus thuringiensis δ-endotoxin, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

[0910] Of note are insecticides such as abamectin, acetamiprid, acralthrin, bicyclanil, amitraz, avermectin, azadirachtin, benfuracarb, sulfamethoxam, bifenthrin, buprofezin, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cypermethrin, cyfluthrin, beta-cyhalothrin, cyhalothrin, beta-cyhalothrin, chlorfenapyr, chlorpyrifos, chlorfenapyr ... Cypermethrin, highly effective chlorflucythrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, benzylpezil, emamectin, endosulfan, cypermethrin, ethomethrin, etoxazole, fenitrothion, fenthiocarb, fenoxycarb, cypermethrin, fipronil, flumetol, flonicamid, flubendiamide, flufenoxuron, flutolanil, diflubenzuron, flupyraclostrobin, Flupyralidone, fluvalinate, flumethrin, thiamethoxam, tefluthrin, hexaflumuron, hydrazone, imidacloprid, indoxacarb, lufenuron, chlorfluthrin, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, metofluthrin, monofluthrin, nitenpyram, nithiazine, flufenacet, oxamyl, flubutamide, pymetrozine, pyrethrin, pyridaben , pyridalyl, cypermethrin, pyriproxyfen, ryanodine, ethyl spinosad, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetrathrin, tetrafluthrin, thiacloprid, thiomethoxam, thiodicarb, dimehypo, tralomethrin, triazolam, triflumuron, Bacillus thuringiensis δ-endotoxin, all strains of Bacillus thuringiensis and all strains of nuclear polyhedrosis virus.

[0911] One example of a biological agent for admixture with the compounds of the present invention includes entomopathogenic bacteria such as Bacillus thuringiensis, and Encapsulated delta-endotoxins of Bacillus thuringiensis prepared by the process, such as and Bioinsecticides ( and is a trademark of Mycogen Corporation, Indianapolis, Indiana, USA); entomopathogenic fungi, such as green muscardine fungus; and entomopathogenic (naturally occurring and genetically modified) viruses, including baculoviruses, nuclear polyhedrosis viruses (NPVs), such as Spodoptera nucleopolyhedrovirus (HzNPV), Anagrapha falcifera nucleopolyhedrovirus (AfNPV); and granuloviruses (GVs), such as Cydia pomonella granulosis virus (CpGV).

[0912] Of particular note are combinations in which the other invertebrate pest control active ingredient belongs to a different chemical class than the compound of Formula 1 or has a different site of action than the compound. In some cases, combinations with at least one other invertebrate pest control active ingredient having a similar control spectrum but a different site of action can be particularly advantageous for resistance management. Therefore, the compositions of the present inven...

Claims

1. A compound having formula 1 (including all geometric and stereoisomers), its N-oxide and salt: in, X is O or S; Each A is independently CH, N or CR 1 ; Each R 1 are independently H, amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replace; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 , SF5, SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 ) p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, when a nitrogen atom is present, by C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace; R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or R 2 is a C1-C6 alkyl group, which is optionally substituted by one or more R 6 substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 Replace; or R 2 It is C(O)R 7 、C(O)OR 7 NR 7 R 8 , OR 7 、S(O)pR 9 or SO2NR 7 R 8 ; R 3 is C1-C3 alkyl or C1-C3 haloalkyl; R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or R 4 It is C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ; R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or R 5 It is C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 ; Each R 6 are independently halogen, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C3-C7 cycloalkyl, C3-C9 trialkylsilyl, C(O)OR 10 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or S(=NR)O p R 7 ; Each R 7 are independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, or C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl or cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 12 Replace; or R 7 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 12 replace; Each R 8 are independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C3-C6 alkenyloxy, C2-C6 alkynyl, or C3-C6 alkynyloxy, wherein alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, or alkynyloxy are each optionally substituted by one or more R 6 replace; When R 7 and R 8 When on N, R 7 and R 8 A ring of 3 to 7 carbon atoms may be formed, the ring optionally containing oxygen, S(O)p or NR 7 ; Each R 9 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl, wherein the alkyl, alkenyl, alkynyl or cycloalkyl are each optionally substituted by one or more R 6 Replace; or R 9 is phenyl, or a 4- to 6-membered saturated, partially saturated or fully unsaturated heterocyclic ring containing ring members selected from carbon atoms and 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, wherein the phenyl or 4- to 6-membered heterocyclic ring are each optionally replaced by one or more R 6 replace; Each R 10 are independently H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyl-C1-C3-alkyl, C1-C3 alkoxy-C1-C3-alkyl; Each R 11 are independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution; C(O)R 7 、C(O)OR 7 , or S(O) p R 7 ; R 12 is halogen, hydroxy, cyano, nitro, SF5, C(O)NH2, C(S)NH2, C1-C3 alkyl, C1-C3 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C8 cycloalkylalkyl, wherein alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted with halogen or cyano; Q is pyridine, pyridazine, pyrimidine, pyrazine, or thiazole, wherein the pyridine, pyridazine, pyrimidine, or pyrazine is optionally substituted with one to three groups, and wherein thiazole is optionally substituted with one to two groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl is each optionally substituted with one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, by C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace; n is 1, 2, or 3; p is 0, 1, or 2.

2. The compound according to claim 1, wherein X is O.

3. The compound according to claim 1, wherein X is S.

4. The compound according to claim 1, wherein A is CH.

5. A compound as claimed in any one of the preceding claims, wherein Where A is N or CR 1 .

6. The compound according to claim 1, wherein X is O; A is CH; and R 3 It's me.

7. A compound as claimed in any one of the preceding claims, wherein R 1 is amino, cyano, halogen, nitro, C(S)NH2; or R 1 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or R 1 is phenyl, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heteroaromatic ring is each optionally replaced by one or more R 6 Replace; or R 1 is C3-C9-trialkylsilyl, C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 ,NR8C(O)R7,NR8C(O)OR7,OR 7 、NHC(O)NR 7 R 8 NR 7 S(O) p R 9 、OC(O)R 7 、OC(O)NR 7 R 8 、OC(O)OR 7 、S(O) p R 9 , SF5, SO2NR 7 R 8 、OS(O)2R 9 , or S(=NR 11 ) p R 9 ; or R 1 is a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, and C1-C3-haloalkoxy, or, when a nitrogen atom is present, by C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 , or SO2NR 7 R 8 replace.

8. A compound as claimed in any one of the preceding claims, wherein R 2 is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C4-C7 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or R 2 is a C1-C6 alkyl group, which is optionally substituted by one or more R 6 substituted and substituted by phenyl, or a 4- to 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 2 nitrogen atoms, or a 5-membered heteroaromatic ring containing ring members selected from carbon atoms and from 1 to 3 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and up to 3 nitrogen atoms, or a 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1 to 2 nitrogen atoms, wherein the phenyl or heterocyclic ring is each optionally substituted by one or more R 6 replace; or R 2 is C(O)R 7 、C(O)OR 7 、NR 7 R 8 、OR 7 、S(O)pR 9 or SO2NR 7 R 8 。 9. The compound according to claim 7, wherein R 2 It is H, CH2c-Pr, or Me.

10. A compound as claimed in any one of the preceding claims, wherein R 4 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or R 4 It is C(O)R 7 , CR 7 (=NO)R 7 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 , or NR 11 SO2NR 7 R 8 ;and R 5 is hydrogen, cyano, halogen, nitro, C(S)NH2, SCN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, or C4-C8-cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Replace; or R 5 It is C(O)R 7 , CR 7 (=NO)R 8 、C(O)OR 7 、C(O)NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 NR 11 SO2NR 7 R 8 , OR 7 、S(O) p R 9 , or SO2NR 7 R 8 .

11. A compound as claimed in any one of the preceding claims, wherein Q is pyridine or pyrimidine, which is optionally substituted by one to three groups selected from amino, cyano, halogen, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C8 cycloalkylalkyl, wherein alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl are each optionally substituted by one or more R 6 Substitution, C(O)R 7 , CR 7 (=NOR 8 )、C(O)OR 7 、C(O)NR 7 R 8 、C(S)NR 7 R 8 , OR 7 、S(O) p R 9 、SO2NR 7 R 8 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 、SO2NR 7 R 8 , or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or a 3- to 7-membered partially or fully saturated heterocyclic ring containing ring members selected from carbon atoms and 1-4 heteroatoms independently selected from 1 oxygen atom, 1 sulfur atom and 1-4 nitrogen atoms, which is optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3-haloalkyl, C1-C3-alkoxy and C1-C3-haloalkoxy, or when a nitrogen atom is present, by C(O)R 7 、C(O)OR 7 、C(O)NR 7 R 8 、S(O) p R 7 、SO2NR 7 R 8 replace.

12. A compound as claimed in any one of the preceding claims, wherein Q is selected from Q-1, Q-2, Q-6, Q-7, Q-11, Q-13, Q-14, Q-18, Q-19, Q-20, Q-21, Q-22, Q-23, Q-24, and Q-25.

13. The compound according to claim 1, wherein X is O; A is CH; n is 2; Each R 1 is independently Cl, F, or Br, or R 1 is optionally replaced by one or more R 6 Substituted Me; or R 1 OMe, SF3, or OS(O)2R 9 ; R 2 is hydrogen, C1-C4 alkyl, or C4-C6 cycloalkylalkyl, wherein alkyl or cycloalkylalkyl are each optionally substituted by one R 6 replace; R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted with one or more R 6 Replace, or R 4 YesNR 7 R 8 NR 8 C(O)R 7 , OR 7 , or S(O) p R 9 ;and R 5 is hydrogen, cyano, halogen, nitro, or C1-C3-alkyl, wherein each alkyl or cycloalkyl is optionally substituted by one or more R 6 Replace; or R 5 Yes OR 7 NR 7 R 8 NR 8 C(O)R 7 NR 8 C(O)OR 7 、S(O) p R 7 , or SO2NR 7 R 8 .

14. The compound according to claim 13, wherein R 4 and R 5 Both are not hydrogen.

15. The compound according to claim 1, wherein X is O; A is N or CR 1 ; R 1 is Cl, F, or Br, or R 1 is optionally replaced by one or more R 6 Substituted Me; or R 1 OMe, SF3, or OS(O)2R 9 ; R 2 is hydrogen, C1-C4 alkyl, or C4-C6 cycloalkylalkyl, wherein alkyl or cycloalkylalkyl are each optionally substituted by one R 6 replace; or R 2 It is C(O)R 7 C(O)OR 7 ;and R 4 is hydrogen, cyano, halogen, nitro, or C1-C3 alkyl, wherein the alkyl is optionally substituted with one or more R 6 replace.

16. The compound according to claim 1, wherein The compound is selected from the group consisting of: N-[1-[3-amino-4-cyano-1-(5-cyano-2-pyridyl)-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide, N-[1-[4-cyano-1-(5-cyano-2-pyridyl)-3-(methylamino)-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide, N-Methyl-N-(1-(4-nitro-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzene Formamide, N-(1-(4-cyano-1-(5-cyanopyridin-2-yl)-1H-pyrazol-5-yl)ethyl)-N-methyl-3,5-bis(trifluoromethyl)benzamide, 3-chloro-N-(1-(4-cyano-1-(5-cyanopyridin-2-yl)-1H-pyrazol-5-yl)ethyl)-N-methyl-5-(trifluoromethyl)benzamide, N-(1-(4-cyano-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, N-[1-[3-amino-4-cyano-1-[5-(4-morpholinylcarbonyl)-2-pyridyl]-1H-pyrazol-5-yl]ethyl]-N-methyl-3,5-bis(trifluoromethyl)benzamide, N,N-dimethyl-6-(5-(1-(N-methyl-3,5-bis(trifluoromethyl)benzamido)ethyl)-4-(methylsulfonyl)-1H-pyrazol-1-yl)pyrimidine-4-carboxamide, N-(1-(4-cyano-3-methoxy-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, N-methyl-N-(1-(4-(methylsulfonyl)-1-(pyrazin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, N-(1-(4-nitro-1-(pyrimidin-2-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide, and N-methyl-N-(1-(4-(methylsulfonyl)-1-(6-(trifluoromethyl)pyrimidin-4-yl)-1H-pyrazol-5-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide.

17. A composition comprising a compound as claimed in any one of the preceding claims and at least one component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, optionally further comprising at least one additional biologically active compound or agent.

18. The composition of claim 15, wherein The at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acetamiprid, acralidin, bicyclanil, sulfanil, amitraz, avermectin, azadirachtin, azophos, benfenac, benfuracarb, sulfanil, bifenthrin, bifenazate, bistrifluan, borate, bromofenac, buprofezin, carbaryl, carbofuran, cartap, chlorfenapyr, chlorfenapyr, chlorpyrifos, methyl chlorpyrifos, chlorfenapyr, clofenac, clothianidin, cyanamide, cyclobromofenapyr, triflupyramide, cypermethrin , cyclohexanil, ethazole cypermethrin, flutoxin, cyfluthrin, high-efficiency flutoxin, cyfluthrin, cyfluthrin, cypermethrin, cypermethrin, cis-cypermethrin, ζ-cypermethrin, cyprodinil, cyromazine, deltamethrin, diafenthiuron, diazinon, dichlorvos benzamide, dieldrin, flutoxin, diflubenzuron, tetrafluthrin, dimethoate, dimethoate, dimethoate, benzylpezil, emamectin, endosulfan, cypermethrin, ethiprole, ethoprolin, etoxazole, fenazaquin, fenbutatin, fenitrothion, dithiocarb, fenoxycarb, cypermethrin, cypermethrin, cypermethrin , flubendiamide, flumetolquinone, flonicamid, pyrimidine, triflumizone, flubendiamide, fluchlorfenapyr, flucythrinate, flupyramid, flufenoxuron, flutolane ... Afenphos, isoxazole amide, κ-tefluthrin, methoprene, lufenuron, malathion, chlorfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, methoxyfenozide, methoxyfluthrin, monocrotophos, monofluthrin, nicotine, N-[1,1-dimethyl-2-(methylthio)ethyl]-7-fluoro-2-(3-pyridyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridyl)-2H-indazole-4-carboxamide, N-[1,1-dimethyl-2-(methylsulfinyl)ethyl]-7-fluoro-2-(3-pyridyl)-2H-indazole-4-carboxamide,1-dimethyl-2-(methylsulfonyl)ethyl]-7-fluoro-2-(3-pyridyl)-2H-indazole-4-carboxamide, N-(1-methylcyclopropyl)-2-(3-pyridyl)-2H-indazole-4-carboxamide, N-[1-(difluoromethyl)cyclopropyl]-2-(3-pyridyl)-2H-indazole-4-carboxamide, nitenpyram, nithiazine, fluorine Urea, polyflumuron, oxamyl, oxazolidinone, parathion, methyl parathion, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, fenthrin, pyrethrin, pyrethrin, pyrethrin, pyrethrin, pyrimidine, pyraclostrobin, pyrethrin, pyrimidine, pyraclostrobin, pyriproxyfen, pyrimidine, pyraclostrobin, pyriproxyfen , rotenone, ryanodine, flutosan, dispirothrin, ethyl spinosad, spinosad, spiroclofen, spirodiclofen, spiromesifen, spirotetramat, sulfaprophos, sulfoxaflor, fenpyraclostrobin, tebuconazole, tebuconazole, flubenzuron, tefluthrin, κ-tefluthrin, terbufos, tetrachlorvinphos, cypermethrin, tetrafluthrin, tetrafluthrin, thiamethoxam, thiodicarb, cypermethrin, thiomethoxam, thiodicarb, thiomethoxam ...

19. A method for controlling and combating invertebrate pests, the method comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound as claimed in any one of claims 1 to 16.

20. A treated seed comprising a compound of any one of claims 1-16 in an amount from about 0.0001% to 1% by weight of the seed before treatment.

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