Herbicidal cyclic amides n-substituted with haloalkylsulfonylanilide groups

Abstract

Disclosed is a compound of formula 1, all stereoisomers, N-oxides, and salts thereof, wherein R 1 ~R 8 , R f , Q, and G are as defined herein. Also disclosed are compositions containing a compound of Formula 1, and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or composition of the invention. [Formula 1] TIFF2024506366000098.tif58170

Description

[Technical Field]

[0001] The present invention relates to specific haloalkylsulfon anilides, their N-oxides, salts and compositions, and methods of using them to control undesirable vegetation. [Background technology]

[0002] Controlling undesirable vegetation is crucial for achieving high yield efficiency. In particular, selective control of weed proliferation in useful crops such as rice, soybeans, sugar beets, corn, potatoes, wheat, barley, tomatoes, and plantation crops is highly desirable. Leaving weed proliferation unchecked in such useful crops can significantly reduce productivity, thereby leading to increased costs for consumers. Controlling undesirable vegetation in uncultivated land is also important. While many products are available on the market for these purposes, there is still a need for novel compounds that are more effective, less expensive, less toxic, more environmentally safe, or possess different mechanisms of action. [Overview of the project] [Means for solving the problem]

[0003] The present invention relates to the compound of formula 1, all stereoisomers thereof, N-oxides, and salts, agricultural compositions containing them, and their use as herbicides. [ka] During the ceremony, R 1is H, C1-C7 alkyl, halogen, CN, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, or C2-C7 haloalkoxyalkyl; R 2 is H, C1-C7 alkyl, halogen, CN, C1-C7 haloalkyl, C1-C7 alkoxy, or C1-C5 alkylthio; R 3 is H, C1-C7 alkyl, halogen, CN, C2-C6 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, or C2-C7 haloalkoxyalkyl; R 4 is H, C(=O)R 14 -C(=S)R 14 -CO2R 14 -C(=O)SR 14 -S(O)2R 14 C(=O)NR 13 R 14 -S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 or CH2OC(=O)R 14 ; or propargyl, allyl, or benzyl; R 5 is H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C3-C7 alkylthioalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 6 These are H, C1-C7 alkyl, halogen, CN, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 haloalkoxyalkyl, or C4-C7 alkylcycloalkyl; R 7 These are H, C1-C7 alkyl, halogen, CN, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 haloalkoxyalkyl, or C4-C7 alkylcycloalkyl; R 8 These are H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; Q is CHR 9 , O, or direct bond; R 9is H, C1-C7 alkyl, halogen, CN, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C7 haloalkoxyalkyl, or C4-C7 alkylcycloalkyl; G is OR 10 , SR 10 , SOR 10 , or SO2R 10 ; or G and R 5 together form N-OR 15 ; R 10 is H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C1-C6 nitroalkyl, C3-C6 alkylcarboalkyl, C3-C6 alkoxycarboalkyl, C2-C7 haloalkoxyalkyl, benzyl, or C3-C6 alkylcarbalkoxy; or R 10 is

Chemical formula

[0004] More specifically, the present invention relates to the compounds of Formula 1, all stereoisomers thereof, N-oxides, or salts. The present invention also relates to herbicidal compositions comprising the compounds of the present disclosure (i.e., a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents. The present invention further relates to a method for controlling the proliferation of undesirable vegetation, comprising contacting vegetation or its environment with a herbicidally effective amount of the compounds of the present disclosure (e.g., as a composition described herein).

[0005] The present invention also comprises (a) a compound selected from Formula 1, all stereoisomers, N-oxides, and salts thereof, and (b) at least one further active ingredient selected from (b1) to (b16) below, and salts of the compounds of (b1) to (b16). [Modes for carrying out the invention]

[0006] As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “contains,” “containing,” “has,” “having,” and “characterized by,” or their various variations, are intended to cover non-exclusive inclusion, subject to any expressly indicated limitations. For example, a composition, mixture, process, method, article, or apparatus containing any element is not necessarily limited to that element alone, and may also include other elements not expressly indicated or inherent in such composition, mixture, process, method, article, or apparatus.

[0007] The transitional phrase "consisting of" excludes any unspecified elements, steps, or components. In patent claims, it is usually associated with a claim that closes by encompassing a substance different from those cited, apart from impurities. If the phrase "consisting of" appears within the main clause of a claim rather than immediately following a preamble, it limits only the elements mentioned in that claim; other elements are not excluded from the claim as a whole.

[0008] The transitional phrase "consisting essentially of" is used to define a composition, method, or apparatus that includes substances, steps, components, or elements, in addition to those disclosed in the text, but where these additional substances, steps, components, or elements do not significantly affect the basic and novel characteristics of the claimed invention. The term "consisting essentially of" occupies a middle ground between "comprising" and "consisting of."

[0009] If an applicant defines an invention or part thereof using an open-ended term such as "comprising," it should be readily understood that (unless otherwise stated) that the description also describes such inventions that use the terms "consisting essentially of" or "consisting of."

[0010] Furthermore, conversely, unless explicitly stated, "or" refers to an inclusive "or" and not an exclusive "or". For example, the condition "A or B" is satisfied by any 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).

[0011] Furthermore, the indefinite articles "a" and "an" preceding the elements or components of the present invention are not restrictive with respect to the number of occurrences of that element or component. Thus, "a" and "an" should be read as including one or at least one, and such singular forms of the element or component also include plurals unless it is clear that the number means singular.

[0012] Where used herein, the term “seedling” is used alone or in combination with other words to mean a young plant developing from the embryo of a seed.

[0013] Where used herein, the term “broadleaf,” either alone or in phrases such as “broadleaf weeds,” means dicotyledonous plants or dicotyledons, and is a term used to describe a group of angiosperms characterized by an embryo having two cotyledons.

[0014] In the above citations, the term "alkyl," used alone or in compound terms such as "alkylthio" or "haloalkyl," includes linear or branched alkyls such as methyl, ethyl, n-propyl, i-propyl, or different butyl, pentyl, or hexyl isomers. "Alkenyl" includes linear or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, and different butenyl, pentenyl, and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkenylalkyl" means alkenyl substitution on an alkyl group. Examples of "alkenylalkyl" include CH2=CHCH2, CH3CH=CHCH2, CH2=CHCH2CH2, CH2=CHCH(CH3)CH2, and different alkenylalkyl isomers. "Alkenylalkyl" is a subset of "alkenyl." "Alkynnyl" includes linear or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl, CH≡CCH2CH2, CH3C≡≡CCH2, and different butynyl, pentynyl, and hexynyl isomers. "Alkynnyl" also includes moieties composed of multiple triple bonds, such as 2,5-hexadiniyl. "Alkynylalkyl" means alkynyl substitution on an alkyl group. Examples of "alkynylalkyl" include CH≡CCH2, CH3C≡≡CCH2, CH≡CCH2CH2, CH≡CCH(CH3)CH2, and different alkynylalkyl isomers. "Alkynylalkyl" is a subset of "alkynyl". "Alkylene" means linear or branched alkanediyl. Examples of "alkylenes" include CH2, CH2CH2, CH(CH3), CH2CH2CH2, CH2CH(CH3), and different butylene isomers. "Alkenylene" refers to linear or branched alkenediyl containing one olefin bond. Examples of "alkenylenes" include CH=CH, CH2CH=CH, CH=C(CH3), and different butenylene isomers. "Alkynylene" refers to linear or branched alkynediyl containing one triple bond.Examples of "alkynylenes" include C≡C, CH2C≡C, C≡CCH2, and different butynylene isomers.

[0015] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, and different butoxy, pentoxy, and hexyloxy isomers. "Alkoxyalkyl" means alkoxy substitution on an alkyl group. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2, and CH3CH2OCH2CH2. "Alkoxyalkoxy" means alkoxy substitution on an alkoxy group. "Alkenyloxy" includes linear or branched alkenyloxy moieties. Examples of "alkenyloxy" include H2C=CHCH2O, (CH3)2C=CHCH2O, (CH3)CH=CHCH2O, (CH3)CH=C(CH3)CH2O, and CH2=CHCH2CH2O. "Alkynyloxy" includes linear or branched alkynyloxy moieties. Examples of "alkynyloxy" include HC≡CCH2O, CH3C≡CCH2O, and CH3C≡CCH2CH2O. "Alkylthio" includes methylthio, ethylthio, and branched or linear alkylthio moieties such as different propylthio, butylthio, pentylthio, and hexylthio isomers. "Alkylsulfinyl" includes both enantiomers of the alkylsulfinyl group. Examples of "Alkylsulfinyl" include CH3S(O)-, CH3CH2S(O)-, CH3CH2CH2S(O)-, (CH3)2CHS(O)-, and different butylsulfinyl, pentylsulfinyl, and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and different butylsulfonyl, pentylsulfonyl, and hexylsulfonyl isomers. "Alkylthioalkyl" means alkylthio substitution on an alkyl group. Examples of "alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2, and CH3CH2SCH2CH2. "Alkylthioalkoxy" means alkylthio substitution on an alkoxy group."Alkyldithio" refers to a branched or linear alkyldithio moiety. Examples of alkyldithio include CH3SS-, CH3CH2SS-, CH3CH2CH2SS-, (CH3)2CHSS-, and different butyldithio and pentyldithio isomers. "Cyanoalkyl" refers to an alkyl group substituted with one cyano group. Examples of cyanoalkyl include NCCH2, NCCH2CH2, and CH3CH(CN)CH2. "Alkylamino," "dialkylamino," "alkenylthio," "alkenylsulfinyl," "alkenylsulfonyl," "alkynylthio," "alkynylsulfinyl," and "alkynylsulfonyl" are defined similarly to the examples above.

[0016] "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "alkylcycloalkyl" means alkyl substitution on a cycloalkyl moiety, and includes, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl, and 4-methylcyclohexyl. The term "cycloalkylalkyl" means cycloalkyl substitution on an alkyl moiety. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to linear or branched alkyl groups. Examples of "alkylcycloalkylalkyl" include 2-methylcyclopropylmethyl, methylcyclopentylethyl, and other alkylcycloalkyl moieties bonded to linear or branched alkyl groups. The term "cycloalkoxy" means cycloalkyls bonded via an oxygen atom, such as cyclopentyloxy and cyclohexyloxy. "Cycloalkylalkoxy" means cycloalkylalkyls bonded via an oxygen atom bonded to an alkyl chain. Examples of "cycloalkylalkoxy" include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to linear or branched alkoxy groups. "Cyanocycloalkyl" refers to a cycloalkyl group substituted with one cyano group. Examples of "cyanocycloalkyl" include 4-cyanocyclohexyl and 3-cyanocyclopentyl. "Cycloalkenyl" includes groups such as cyclopentenyl and cyclohexenyl, as well as groups with multiple double bonds such as 1,3- and 1,4-cyclohexadienyl.

[0017] The term "halogen" includes fluorine, chlorine, bromine, or iodine when used alone, in compound terms such as "haloalkyl," or in descriptions such as "halogen-substituted alkyl." Furthermore, when used in compound terms such as "haloalkyl" or in descriptions such as "halogen-substituted alkyl," the alkyl may be partially or completely substituted with the same or different halogen atoms. Examples of "haloalkyl" or "halogen-substituted alkyl" include F3C, ClCH2, CF3CH2, and CF3CCl2. The terms "halocycloalkyl," "haloalkoxy," "haloalkylthio," "haloalkenyl," and "haloalkynyl" are defined similarly to "haloalkyl." Examples of "haloalkoxy" include CF3O-, CCl3CH2O-, HCF2CH2CH2O-, and CF3CH2O-. Examples of "haloalkylthio" include CCl3S-, CF3S-, CCl3CH2S-, and ClCH2CH2CH2S-. Examples of "haloalkylsulfinyl" include CF3S(O)-, CCl3S(O)-, CF3CH2S(O)-, and CF3CF2S(O)-. Examples of "haloalkylsulfonyl" include CF3S(O)2-, CCl3S(O)2-, CF3CH2S(O)2-, and CF3CF2S(O)2-. Examples of "haloalkenyl" include (Cl)2C=CHCH2- and CF3CH2CH=CHCH2-. Examples of "haloalkynyl" include HC≡CCHCl-, CF3C≡C-, CCl3C≡C-, and FCH2C≡CCH2-. Examples of "haloalkoxyalkoxy" include CF3OCH2O-, ClCH2CH2OCH2CH2O-, Cl3CCH2OCH2O-, and branched alkyl derivatives. Examples of "halolalkoxyalkyls" include CF3OCH2-, ClCH2CH2OCH2CH2, Cl3CCH2OCH2CH2-, and branched alkyl derivatives.

[0018] "Alkylcarbonyl" refers to a linear or branched alkyl moiety bonded to the C(=O) portion. Examples of "alkylcarbonyl" include CH3C(=O)-, CH3CH2CH2C(=O)-, and (CH3)2CHC(=O)-. "Alkylcarboalkoxy" refers to a linear or branched alkoxy substituted with an alkylcarbonyl group. Examples of "alkylcarboalkoxy" include CH3C(=O)CH2O-, CH3CH2CH2C(=O)CH2O-, and (CH3)2CHC(=O)CH2CH2O-. Examples of "alkoxycarbonyl" include CH3OC(=O)-, CH3CH2OC(=O)-, CH3CH2CH2OC(=O)-, (CH3)2CHOC(=O)-, and different butoxy or pentoxycarbonyl isomers. "Alkoxycarboalkyl" refers to linear or branched alkyl groups substituted with alkoxycarbonyl groups. Examples of "alkoxycarboalkyl" include CH3OC(=O)CH2-, CH3CH2OC(=O)CH2CH2-, CH3CH2CH2OC(=O)CH2-, (CH3)2CHOC(=O)CH(CH3)CH2-, and different butoxy or pentoxycarbonyl alkyl isomers.

[0019] The total number of carbon atoms in a substituent is indicated by the prefix "C". i ~C j This is represented by '', where i and j are numbers from 1 to 7. In other words, i and j indicate the total number of carbon atoms in the group, and i to j indicate the range of possible total numbers of carbon atoms in the group. For example, C1-C4 alkylsulfonyls range from methylsulfonyl to butylsulfonyl; C2-C6 alkenyls range from ethenyl to hexenyl, as well as different propenyl, butenyl, pentenyl, and hexenyl isomers. C2 alkoxyalkyls represent CH3OCH2-; C3 alkoxyalkyls represent, for example, CH3CH(OCH3)-, CH3OCH2CH2-, or CH3CH2OCH2-; and C4 alkoxyalkyls represent various isomers of alkyl groups substituted with alkoxy groups, containing a total of four carbon atoms, for example, CH3CH2CH2OCH2- and CH3CH2OCH2CH2-.

[0020] substituents whose group can be hydrogen, for example, R 2 If the group contains a substituent, and this substituent is hydrogen, this is considered equivalent to the group being unsubstituted at this position. When one or more positions of the group are said to be "unsubstituted," a hydrogen atom is bonded to them and occupies any free valence.

[0021] Substituents G, R 8 , R 11 , or R 12 The linkage points of these substituents are not shown fixed, meaning that each of these substituents can be linked to any of the available carbon atoms on the ring they link to by substituting a hydrogen atom. For example, G or R 8 Q can be linked to any ring carbon having available valence by substitution of hydrogen atoms, and the ring is a cyclic amide ring represented by formula 1. For example, Q is CHR 9 In that case, G is CHR 9 By substituting H into the carbon, C(G)R 9 It can form a part of R. 11 or R 12 It can be linked to any ring carbon having available valence by substitution of hydrogen atoms, and the ring is R as outlined in this disclosure. 10 -1~R 10 As shown in -16. In this disclosure, the cyclic amide ring always has substituent G.

[0022] Unless otherwise specified, the “ring” as a component of Formula 1 is either a carbocyclic or heterocyclic structure. For example, a cyclic amide ring is a ring containing an N-CO group, which can optionally contain more heteroatoms as ring members. The term “ring member” refers to an atom or other part (e.g., C(=O), C(=S), S(O), or S(O)2) that forms the skeleton of a ring or ring system.

[0023] Some non-limiting examples of cyclic amide rings in this disclosure are shown in the table in Appendix 1, where each structure is associated with L-#, where # is a number. If a substituent on the cyclic amide ring is G, but other substituents on the same carbon to which G is bonded are not specified (e.g., L-2, L-4, L-6, L-8, L-10, L-12, L14, L-16, and L-18), then H or R 8 G and R can occupy the remaining valence on the carbon. 5 They are combined into N-OR 15 It can also form a double bond, where N is linked to a carbon ring member, forming an oxime moiety such as L-19. [ka]

[0024] In one particular embodiment, G and R 5 Together, N-OR 15 This can form a structure where N is linked to the carbon ring member via a double bond, forming an oxime moiety as shown below. [ka]

[0025] The terms “heterocyclic ring,” “heterocycle,” or “heterocyclic system” refer to a ring or ring system in which at least one atom forming the ring skeleton is not carbon, for example, nitrogen, oxygen, or sulfur. Typically, a heterocyclic ring contains up to four nitrogen atoms, up to two oxygen atoms, and up to two sulfur atoms. Unless otherwise indicated, a heterocyclic ring can be saturated, partially unsaturated, or completely unsaturated. If a completely unsaturated heterocyclic ring satisfies Hückel's rule, the ring is also called a “heteroaromatic ring” or “aromatic heterocyclic ring.” Unless otherwise indicated, heterocyclic rings and ring systems can be bonded via any available carbon or nitrogen atoms by substitution of hydrogen atoms on carbon or nitrogen atoms.

[0026] "Aromatic" indicates that each ring atom is essentially in the same plane, has a p orbital perpendicular to the ring plane, and (4n+2)π electrons (n ​​is a positive integer) are associated with the ring according to Hückel's law. The term "aromatic ring system" means a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic. The term "aromatic carbocyclic system" means a carbocyclic system in which at least one ring of the ring system is aromatic. The term "aromatic heterocyclic system" means a heterocyclic system in which at least one ring of the ring system is aromatic. The term "non-aromatic ring system" means a carbocyclic or heterocyclic ring system that is fully saturated, partially unsaturated, or fully unsaturated, provided that the rings in the ring system are not aromatic. The term "non-aromatic carbocyclic system" means a ring system in which none of the rings are aromatic. The term "non-aromatic heterocyclic system" means a heterocyclic system in which none of the rings are aromatic.

[0027] In relation to heterocycles, the term “optionally substituted” refers to a group having at least one non-hydrogen substituent that does not negate the biological activity of the unsubstituted group or its unsubstituted analogue. As used herein, unless otherwise indicated, the following definitions apply: The term “optionally substituted” is used interchangeably with the phrases “substituted or unsubstituted” or the term “(un)substituted.” Unless otherwise indicated, an optionally substituted group may have substituents at each of its substituted positions, and each substitution is independent of the others.

[0028] In Equation 1, G is OR 10 , SR 10 SOR 10 Or SO2R 10 , R 10 In that case, NR 5 R 6 This can be J (in particular). Several non-restrictive examples of J are shown in the table in Appendix 2, where each structure is associated with J-#, where # is a number. [ka]

[0029] A wide variety of synthetic methods are known in the art that enable the preparation of aromatic and non-aromatic heterocycles and cyclic systems. For a comprehensive review, please refer to the 8-volume set of *Comprehensive Heterocyclic Chemistry*, edited by ARKatritzky and CWRees, Pergamon Press, Oxford, 1984, and the 12-volume set of *Comprehensive Heterocyclic Chemistry II*, edited by ARKatritzky, CWRees and EFVScriven, Pergamon Press, Oxford, 1996.

[0030] The compounds of the present invention may exist as one or more stereoisomers. Various stereoisomers include enantiomers, diastereomers, atropisomers, and geometricisomers. Stereoiomers are isomers that have the same composition but differ in the arrangement of their atoms in space, and include enantiomers, diastereomers, cis-trans isomers (also known as geometricisomers), and atropisomers. Atropisomers arise from bound rotation around a single bond, where the rotational barrier is high enough to allow the isolation of the isomeric species. Those skilled in the art will recognize that one stereoisomer may be more active and / or exhibit beneficial effects when concentrated relative to or separated from other stereoisomers. Furthermore, those skilled in the art know methods for separating, concentrating, and / or selectively preparing such stereoisomers. The compounds of the present invention may exist as mixtures of stereoisomers, individual stereoisomers, or optically active compounds.

[0031] For example, G and R 5If the atoms differ and are bonded to the same carbon atom, the compound of formula 1 may have at least two stereoisomers. The two stereoisomers are represented as formula 1' and formula 1'', having a chiral center identified by an asterisk (*). For a comprehensive discussion of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994. [ka]

[0032] The molecular depictions described herein follow standard conventions for depicting stereochemistry. To indicate stereochemistry, bonds facing the observer from the plane of the drawing are shown with solid wedges, the broader end of which is bonded to an atom facing the observer from the plane of the drawing. Bonds below the plane of the drawing and away from the observer are shown with dashed wedges, the broader end of which is bonded to an atom away from the observer. Lines of constant width indicate bonds in the opposite or neutral direction to those shown with solid or dashed wedges, and lines of constant width also indicate bonds of molecules or parts of molecules that are not intended to specify a particular stereochemistry.

[0033] The present invention includes a racemic mixture, for example, equal amounts of enantiomers of formula 1' and 1''. Furthermore, the present invention includes a compound concentrated compared to a racemic mixture of enantiomers of formula 1. The present invention also includes a compound of formula 1, for example, an essentially pure enantiomer of formula 1' or formula 1''.

[0034] When enantiomers are concentrated, one enantiomer is present in greater quantities than the other, and the degree of concentration can be defined by the formula for the enantiomer excess ("ee"), which is defined as (2x-1)100%, where x is the mole fraction of the dominant enantiomer in the mixture (for example, 20% ee corresponds to a 60:40 ratio of enantiomers).

[0035] Preferably, the compositions of the present invention have more active isomers having an enantiomer excess of at least 50%, more preferably at least 75%, even more preferably at least 90%, and most preferably at least 94%. Of particular note are the enantiomerically pure embodiments of the more active isomers.

[0036] The compound of formula 1 may contain further chiral centers, for example, G and R. 5 Such substituents and other molecular components may themselves contain chiral centers. The present invention includes racemic mixtures and the concentrated, essentially pure stereochemistry at these additional chiral centers.

[0037] The compounds of the present invention may exist as one or more conformational isomers for any restricted bond rotation in Formula 1. The present invention includes mixtures of conformational isomers. Furthermore, the present invention includes compounds in which one conformational isomer is concentrated compared to other conformational isomers.

[0038] Compounds of formula 1 typically exist in multiple forms, and therefore formula 1 encompasses all crystalline and amorphous forms of the compounds they represent. Amorphous forms include solid embodiments such as waxes and rubbers, as well as liquid embodiments such as solutions and melts. Crystalline forms include embodiments that substantially represent a single crystal type, and embodiments that represent a mixture of polymorphs (i.e., multiple crystalline types). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize in various crystalline forms, and these forms have various arrangements and / or conformations of molecules in the crystal lattice. Multiple polymorphs may have the same chemical composition, but they may also differ in composition depending on the presence or absence of co-crystallized water or other molecules that can be weakly or strongly bonded in their lattice. Polymorphs may differ in terms of chemical, physical, and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspension properties, dissolution rate, and biological availability. As those skilled in the art will acknowledge, polymorphs of the compound of formula 1 can exhibit advantageous effects (e.g., suitability for preparing useful formulations, improved biological performance) compared to other polymorphs of the same compound of formula 1, or mixtures of multiple polymorphs. The preparation and isolation of specific polymorphs of the compound of formula 1 can be achieved by methods known to those skilled in the art, such as crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism, see the following: R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

[0039] Those skilled in the art will recognize that nitrogen-containing heterocycles are not always capable of forming N-oxides because nitrogen requires a lone pair of electrons available for oxidation to oxides. Those skilled in the art will recognize those nitrogen-containing heterocycles that are capable of forming N-oxides. Those skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for preparing heterocycle N-oxides and tertiary amines are well known to those skilled in the art, and include oxidation of heterocycles and tertiary amines with organic peroxy acids, e.g., peracetic acid and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides, e.g., t-butyl hydroperoxide, sodium perborate, and dioxiranes, e.g., dimethyldioxiran. These methods for preparing N-oxides are widely described in the literature, and review articles have been written about them. For example, please refer to the following: TLGilchrist, Comprehensive Organic Synthesis, vol.7, pp 748-750 (SVLey, Ed., Pergamon Press); M.Tisler and B.Stanovnik, Comprehensive Heterocyclic Chemistry, vol.3, pp.18-20 (AJBoulton and A.McKillop, Eds., Pergamon Press); MRGrimmett and BRTKeene, Advances in Heterocyclic Chemistry, vol.43, pp.149-161 (ARKatritzky, Ed., Academic Press); M.Tisler and B.Stanovnik, Advances in Heterocyclic Chemistry, vol.9, pp.285-291 (ARKatritzky and AJ Boulton, Eds., Academic Press); and GWHCheeseman and ESGWerstiuk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392 (ARKatritzky and AJ Boulton, Eds., Academic Press).

[0040] Those skilled in the art will recognize that, under environmental and physiological conditions, salts of compounds are in equilibrium with their corresponding unsalted forms, and therefore salts share the biological utility of the unsalted forms. Thus, a wide variety of salts of the compounds of Formula 1 are useful for controlling undesirable vegetation (i.e., suitable for agriculture). Salts of the compounds of Formula 1 include acid addition salts with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. If the compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, the salts also include those formed with pyridine, triethylamine, or ammonia, or with organic or inorganic bases such as amides, hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium, or barium. Therefore, the present invention includes compounds selected from Formula 1, their N-oxides, and agriculturally suitable salts.

[0041] The embodiments of the present invention described in the summary of the disclosure include those in which the compound of Formula 1 is described in any of the following embodiments:

[0042] Embodiment 1. Compounds of Formula 1 as described in the summary of the disclosure, all stereoisomers thereof, N-oxides, and salts, agricultural compositions containing them, and their use as herbicides as described in the summary of the disclosure.

[0043] Embodiment 2.Q is CHR 9 A compound of formula 1 or embodiment 1, wherein the bond is O, or a direct bond.

[0044] Embodiment 2a.Q is CHR 9 A compound of formula 1 or embodiment 2, which is either directly bonded or directly bonded.

[0045] Embodiment 2b.Q is CHR 9 A compound of formula 1 or embodiment 2a.

[0046] Embodiment 2c. A compound of formula 1 or embodiment 2a in which Q is a direct bond.

[0047] Embodiment 2d. A compound of formula 1 or Embodiment 2, wherein Q is O.

[0048] Embodiment 3.R 1 The compound is one of the compounds of formula 1 or the preceding embodiments, wherein the compound is H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C1-C7 haloalkyl.

[0049] Embodiment 3a.R 1 The compound of Embodiment 3 is H, C1-C7 alkyl, halogen, and C3-C7 cycloalkyl.

[0050] Embodiment 3b.R 1 The compound of Embodiment 3a, wherein the compound is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl.

[0051] Embodiment 3c.R 1 The compound of Embodiment 3b, wherein the compound is H, Me, halogen, or cyclopropyl.

[0052] Embodiment 3d.R 1 The compound of Embodiment 3c, wherein the element is H, Me, F, Cl, Br, or cyclopropyl.

[0053] Embodiment 3e.R 1 The compound of embodiment 3d, wherein the compound is Me or Cl.

[0054] Embodiment 3f.R 1 A compound of embodiment 3e, wherein Me is present.

[0055] Embodiment 3g.R 1 The compound of embodiment 3e, wherein the compound is Cl.

[0056] Embodiment 3h.R 1 The compound of embodiment 3d, wherein is H.

[0057] Embodiment 4.R 2A compound of formula 1 or any one of the previous embodiments, wherein R is H, C1-C7 alkyl, halogen, CN, C1-C7 haloalkyl, C1-C7 alkoxy, or C1-C5 alkylthio.

[0058] Embodiment 4a. R 2 A compound of Embodiment 4, wherein R is H, C1-C7 alkyl, halogen, or CN.

[0059] Embodiment 4b. R 2 A compound of Embodiment 4a, wherein R is H, Me, F, Cl, or CN.

[0060] Embodiment 4c. R 2 A compound of Embodiment 4b, wherein R is H or F.

[0061] Embodiment 4d. R 2 A compound of Embodiment 4c, wherein R is H.

[0062] Embodiment 4e. R 2 A compound of Embodiment 4c, wherein R is F.

[0063] Embodiment 5. R 3 A compound of formula 1 or any one of the previous embodiments, wherein R is H, C1-C7 alkyl, halogen, CN, C2-C6 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, or C2-C7 haloalkoxyalkyl.

[0064] Embodiment 5a. R 3 A compound of Embodiment 5, wherein R is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl.

[0065] Embodiment 5b. R 3 A compound of Embodiment 5a, wherein R is H, Me, F, Cl, CN, OMe, or CF3.

[0066] Embodiment 5c.R 3 The compound of Embodiment 5b where is Me or F.

[0067] Embodiment 5d.R 3 The compound of Embodiment 5c where is Me.

[0068] Embodiment 6.R<00,00094>is H, C(=O)R 14 C(=S)R 14 C(=O)OR 14 C(=O)SR 14 S(O)2R 14 C(=O)NR 13 R 14 S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 or CH2OC(=O)R[[ID=For]] 14 ; or the compound of Formula 1 or any one of the previous embodiments which is propargyl, allyl, or benzyl. <00,01196>

[0069] Embodiment e.R 4 is H, C(=O)R[[ID=A]] 14 C(=S)R 14 C(=O)OR 14 C(=O)SR 14 S(O)2R 14 C(=O)NR 13 R 14 S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 or CH2OC(=O)R 14 of the compound of Formula 1 or any one of the previous embodiments.

[0070] Embodiment 6aa.R 4 is H, C(=O)R 14 CO2R 14 ]>C(=O)SR 14S(O)2R 14 CH2OC(=O)OR 14 , or CH2OCOR 14 The compound of Embodiment 6.

[0071] Embodiment 6b.R 4 The compound of Embodiment 6aa, wherein the compound is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-t-Bu, CH2OCO-n-Bu, CH2OCO-c-hexyl, CH2OCO-c-pentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-i-Bu, CH2OCOMe, CH2OCO-sec-Bu, CH2OCO-n-Pr, CH2OCO-i-Pr, or (C=O)SMe.

[0072] Embodiment 6c.R 4 However, H, CH2OCOR 14 , or -S(O)2R 14 The compound of embodiment 6a.

[0073] Embodiment 6d.R 4 The compound of Embodiment 6c, wherein the compound is H, CH2OCO-t-Bu, or S(O)2CF3.

[0074] Embodiment 6e.R 4 The compound of embodiment 6d, wherein is H.

[0075] Embodiment 6f.R 4 The compound of embodiment 6d, wherein is S(O)2CF3.

[0076] Embodiment 6g.R 4 The compound of Embodiment 6, wherein the compound is propargyl, allyl, or benzyl.

[0077] Embodiment 6h.R 4 A compound of embodiment 6 g, wherein the compound is benzyl.

[0078] Embodiment 6g.R 4 The compound of Embodiment 6, wherein propargyl is present.

[0079] Embodiment 6g.R 4 The compound of Embodiment 6, wherein the compound is allyl.

[0080] Embodiment 7.R 5 A compound of any one of the embodiments of Formula 1 or the preceding embodiment, wherein the compound is H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl.

[0081] Embodiment 7a.R 5 The compound of Embodiment 7, wherein the compound is H, C4-C7 cycloalkylalkyl, or C2-C7 alkoxyalkyl.

[0082] Embodiment 7b.R 5 The compound of embodiment 7a, wherein is H.

[0083] Embodiment 8.R 6 A compound of any one of the embodiments of Formula 1 or the preceding embodiment, wherein the compound is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, or C4-C7 alkylcycloalkyl.

[0084] Embodiment 8a.R 6 The compound of Embodiment 8, wherein the compound is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy.

[0085] Embodiment 8b.R 6The compound of Embodiment 8a, wherein the compound is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy.

[0086] Embodiment 8c.R 6 The compound of Embodiment 8b, wherein the compound is H, C1-C7 alkyl, or C1-C7 alkoxy.

[0087] Embodiment 8d.R 6 The compound of Embodiment 8b, wherein the element is H, Me, or OMe.

[0088] Embodiment 8e.R 6 The compound of embodiment 8d, wherein is H.

[0089] Embodiment 8f.R 6 The compound of embodiment 8d, wherein Me is present.

[0090] Embodiment 8g.R 6 The compound of embodiment 8d, wherein OMe is present.

[0091] Embodiment 9.R 7 A compound of any one of the embodiments of Formula 1 or the preceding embodiment, wherein the compound is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, or C4-C7 alkylcycloalkyl.

[0092] Embodiment 9a.R 7 The compound of Embodiment 9, wherein the compound is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy.

[0093] Embodiment 9b.R 7 The compound of Embodiment 9a is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy.

[0094] Embodiment 9c.R 7 The compound of Embodiment 9b, wherein the compound is H, C1-C7 alkyl, or C1-C7 alkoxy.

[0095] Embodiment 9d.R 7 The compound of Embodiment 9b, wherein the element is H, Me, or OMe.

[0096] Embodiment 9e.R 7 The compound of embodiment 9d, wherein is H.

[0097] Embodiment 9f.R 7 The compound of embodiment 8d, wherein Me is present.

[0098] Embodiment 9g.R 7 The compound of embodiment 9d, wherein OMe is present.

[0099] Embodiment 10.R 8 A compound of any one of the embodiments of Formula 1 or the preceding embodiment, wherein the compound is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl.

[0100] Embodiment 10a.R 8The compound of Embodiment 10, wherein the compound is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy.

[0101] Embodiment 10b.R 8 The compound of Embodiment 10a is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy.

[0102] Embodiment 10c.R 8 The compound of Embodiment 10b, wherein the compound is H, C1-C7 alkyl, or C1-C7 alkoxy.

[0103] Embodiment 10d.R 8 The compound of Embodiment 10b, wherein the compound is H, Me, or OMe.

[0104] Embodiment 10e.R 8 The compound of embodiment 10d, wherein is H.

[0105] Embodiment 10f.R 8 A compound of embodiment 10d, wherein Me is present.

[0106] Embodiment 10g.R 8 The compound of embodiment 10d, wherein OMe is present.

[0107] Embodiment 11.R 9 A compound of any one of the embodiments of Formula 1 or the preceding embodiment, wherein the compound is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, or C4-C7 alkylcycloalkyl.

[0108] Embodiment 11a.R 9 The compound of Embodiment 11, wherein the compound is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy.

[0109] Embodiment 11b.R 9 The compound of Embodiment 11a is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy.

[0110] Embodiment 11c.R 9 The compound of Embodiment 11b, wherein the compound is H, C1-C7 alkyl, or C1-C7 alkoxy.

[0111] Embodiment 11d.R 9 The compound of embodiment 11b, wherein the element is H, Me, or OMe.

[0112] Embodiment 11e.R 9 The compound of embodiment 11d, wherein is H.

[0113] Embodiment 11f.R 9 A compound of embodiment 11d, wherein Me is present.

[0114] Embodiment 11g.R 9 The compound of embodiment 11d, wherein OMe is present.

[0115] Embodiment 12.G is OR 10 , SR 10 SOR 10 , or SO2R 10 is it; or G and R 5 Together they become N-OR 15 It forms R 15A compound of any one of the embodiments of Formula 1 or the previous embodiment, wherein the compound is H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C4-C7 cycloalkylalkyl.

[0116] Embodiment 12a.G is OR 10 , SR 10 SOR 10 , or SO2R 10 The compound of Embodiment 12.

[0117] Embodiment 12aa.G is OR 10 or SR 10 The compound of embodiment 12a.

[0118] Embodiment 12b.G is OR 10 The compound of embodiment 12aa.

[0119] Embodiment 12c.G is SR 10 The compound of embodiment 12aa.

[0120] Embodiment 12d.G is SOR 10 The compound of Embodiment 12.

[0121] Embodiment 12e.G is SO2R 10 The compound of Embodiment 12.

[0122] Embodiment 12f.G and R 5 The compound of Embodiment 12, wherein the same carbon ring member is linked to the compound of Embodiment 12.

[0123] Embodiment 12g.G and R 5 Together they become N-OR 15 The compound of embodiment 12 that forms [a certain shape].

[0124] Embodiment 12gg.R 15 The compound of Embodiment 12g is H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C4-C7 cycloalkylalkyl.

[0125] Embodiment 12h.R 15 A compound of embodiment 12 g, wherein H is present.

[0126] Embodiment 12i.R 15 The compound of embodiment 12 g, wherein the parent is a C1-C6 alkyl group.

[0127] Embodiment 12j.R 15 The compound of Embodiment 12g, wherein the components are H, Me, Et, CH2CH=CH2, or CH2C≡CH.

[0128] Embodiment 12k.R 15 However, the compound of Embodiment 12j is Me, Et, CH2CH=CH2, or CH2C≡CH.

[0129] Embodiment 12l.G and R 5 The compound of embodiment 12a, in which the same carbon is bonded.

[0130] Embodiment 12m.R 5 A compound of embodiment 12l, wherein H is present.

[0131] Embodiment 12n.G and R 6 The compound of embodiment 12a, in which the same carbon is bonded.

[0132] Embodiment 12o.R 6 A compound of embodiment 12n, wherein H is present.

[0133] Embodiment 12 p.G and R 7 The compound of embodiment 12a, in which the same carbon is bonded.

[0134] Embodiment 12q.R 7 The compound of embodiment 12p, wherein H is present.

[0135] Embodiment 12r.G and R 9 The compound of embodiment 12a, in which the same carbon is bonded.

[0136] Embodiment 12s.R9 A compound of embodiment 12r, wherein H is present.

[0137] Embodiment 13.R 10 is H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C1-C6 nitroalkyl, C3-C6 alkylcarboalkyl, C3-C6 alkoxycarboalkyl, C2-C7 haloalkoxyalkyl, benzyl, or C3-C6 alkylcarboalkoxy; or R 10 but, [ka] A compound selected from the group consisting of formula 1 or one of the earlier embodiments.

[0138] Embodiment 13a.R 10 The compound of Embodiment 13, wherein the compound is H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C7 haloalkoxyalkyl, benzyl, or C4-C7 alkylcycloalkyl.

[0139] Embodiment 13aa.R 10The compound of Embodiment 13a is H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C7 haloalkoxyalkyl, benzyl, or C4-C7 alkylcycloalkyl.

[0140] Embodiment 13b.R 10 The compound of Embodiment 13aa is a C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C2-C4 cyanoalkyl, C3-C7 alkylthioalkyl, benzyl, or C4-C7 alkylcycloalkyl.

[0141] Embodiment 13c.R 10 The compound of Embodiment 13b is a C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, or C4-C7 alkylcycloalkyl.

[0142] Embodiment 13d.R 10 The compound of Embodiment 13c is a C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C4-C7 halocycloalkylalkyl.

[0143] Embodiment 13dd.R 10 The compound of Embodiment 13d is a C2-C6 alkenyl, a C2-C6 alkynyl, or a C3-C7 cycloalkyl.

[0144] Embodiment 13e.R 10The compound of Embodiment 13d is cyclopropyl, cyclobutyl, cyclopentyl, allyl, or propargyl.

[0145] Embodiment 13ee.R 10 A compound of embodiment 13e, wherein H is present.

[0146] Embodiment 13f.R 10 The compound of Embodiment 13e, wherein is cyclopropyl.

[0147] Embodiment 13g.R 10 The compound of Embodiment 13e, wherein the compound is cyclobutyl.

[0148] Embodiment 13gg.R 10 The compound of Embodiment 13e, wherein the compound is cyclopentyl.

[0149] Embodiment 13ggg.R 10 The compound of Embodiment 13e, wherein is cyclohexyl.

[0150] Embodiment 13h.R 10 The compound of embodiment 13e, wherein the compound is allyl.

[0151] Embodiment 13i.R 10 The compound of Embodiment 13e, wherein propargyl is present.

[0152] Embodiment 13j.R 10 However, R 10 -1, R 10 -2, R 10 -3, R 10 -4, R 10 -5, R 10 -6, R 10 -7, R 10 -8, R 10 -9, R 10 -10, R 10 -11, R 10 -12, R 10 -13, R 10 -14, R 10 -15, or R 10 The compound of Embodiment 13, which is -16.

[0153] Embodiment 13k.R 10 However, R 10 -1, R 10 -2, R 10 -3, R 10 -4, R 10 -5, R 10 -6, R 10 -7, R 10 -8, or R 10 Compound of embodiment 13j, which is -9.

[0154] Embodiment 13l.R 10 However, R 10 -3 or R 10 The compound of embodiment 13k is -4.

[0155] Embodiment 13m.R 10 The compound of Embodiment 13a is a C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 halocycloalkylalkyl, C4-C7 cycloalkylalkyl, or benzyl.

[0156] Embodiment 14.R 11 A compound of formula 1 or any of the preceding embodiments, wherein the compound is H or a C1-C7 alkyl group.

[0157] Embodiment 14a.R 11 A compound of either formula 1 or one of the earlier embodiments, wherein H is present.

[0158] Embodiment 15.R 12 A compound of formula 1 or any of the preceding embodiments, wherein the compound is H or a C1-C7 alkyl group.

[0159] Embodiment 15a.R 12 A compound of either formula 1 or one of the earlier embodiments, wherein H is present.

[0160] Embodiment 16. Each R 13 and R 14However, the compound is independently H, C1-C7 haloalkyl, or C1-C7 alkyl, which is one of the compounds of formula 1 or the previous embodiments.

[0161] Embodiment 16a. Each R 13 and R 14 However, the compound of Embodiment 16 is independently a C1-C4 alkyl group.

[0162] Embodiment 16b. Each R 13 and R 14 However, the compound of Embodiment 16a is independently a C1-C3 haloalkyl.

[0163] Embodiment 16c. Each R 13 and R 14 However, the compound of Embodiment 16 is independently CF3.

[0164] Embodiment 17.R f A compound of either Formula 1 or one of the previous embodiments, wherein the compound is a C1-C3 haloalkyl group.

[0165] Embodiment 17a.R f The compound of Embodiment 28, wherein CF3 is present.

[0166] Embodiments of the present invention, including Embodiments 1 to 17a described above and any other embodiments described herein, can be combined in any way, and the descriptions of variables in the embodiments relate not only to the compounds of Formula 1 but also to starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. Furthermore, embodiments of the present invention, including Embodiments 1 to 17a described above and other embodiments described herein, and any combination thereof, relate to the compositions and methods of the present invention.

[0167] Combinations of embodiments 1 to 17a are exemplified below:

[0168] Embodiment A. A compound of Formula 1 as described in the summary of the disclosure, Q is a direct connection; R 1However, these are H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and C1-C7 haloalkyl; R 2 However, it is H, C1-C7 alkyl, halogen, or -CN; R 3 However, it is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R 4 However, H, -C(=O)R 14 -C(=S)R 14 , -CO2R 14 -C(=O)SR 14 -S(O)2R 14 -C(=O)NR 13 R 14 -S(O)2NR 13 R 14 -CH2OC(=O)OR 14 -CH2OC(=O)NR 13 R 14 , or -CH2OC(=O)R 14 and; R 5 However, these are H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 6 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 7 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; G, OR 10 , SR 10 SOR 10 , or SO2R 10 and; R 10 However, these are H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C7 haloalkoxyalkyl, benzyl, or C4-C7 alkylcycloalkyl; R 11 However, it is H or C1-C7 alkyl; R 12 However, it is H or C1-C7 alkyl; Each R 13 and R 14 However, independently, they are H, C1-C7 haloalkyl, or C1-C7 alkyl; R f It is a C1-C3 haloalkyl group; compound.

[0169] Embodiment A1. R 1 However, it is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3 However, it is H, Me, F, Cl, CN, OMe, or CF3; R 4is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-t-Bu, CH2OCO-n-Bu, CH2OCO-c-hexyl, CH2OCO-c-pentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-i-Bu, CH2OCOMe, CH2OCO-sec-Bu, CH2OCO-n-Pr and CH2OCO-i-Pr, or (C=O)SMe; R 5 However, it is H, C4-C7 cycloalkylalkyl, or C2-C7 alkoxyalkyl; R 6 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 7 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; G, OR 10 or SR 10 and; R 10 However, these are C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C2-C4 cyanoalkyl, C3-C7 alkylthioalkyl, benzyl, or C4-C7 alkylcycloalkyl; The compound of Embodiment A.

[0170] Embodiment A2. R 1 However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH2OCOR 14 , or -S(O)2R14 and; R 5 H is; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; G is OR 10 and; R 10 However, these are C2-C6 alkenyls, C2-C6 alkynyls, C3-C7 cycloalkyls, C4-C7 cycloalkylalkyls, C4-C7 halocycloalkylalkyls, or C4-C7 alkylcycloalkyls; Compound of Embodiment A1.

[0171] Embodiment A3. R 1 However, it is H, Me, F, Cl, Br, or cyclopropyl; R 4 However, it is H, CH2OCO-t-Bu, or SO2CF3; R 8 H is; R 10 However, it is a C2-C6 alkenyl, C2-C6 alkynyl, or C3-C7 cycloalkyl. Compound of Embodiment A2.

[0172] Embodiment A4. R 1 That is Me; R 3 That is Me; R 4 H is; R 6 H is; R 7 H is; R 10 However, these are cyclopropyl, cyclobutyl, cyclopentyl, allyl, or propargyl; Compound of Embodiment A3.

[0173] Embodiment B. A compound of Formula 1 as described in the summary of the disclosure, Q is CHR 9 and; R 1 However, these are H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and C1-C7 haloalkyl; R 2 However, it is H, C1-C7 alkyl, halogen, or CN; R 3 However, it is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R 4 However, H, C(=O)R 14 -C(=S)R 14 , -CO2R 14 -C(=O)SR 14 -S(O)2R 14 , C(=O)NR 13 R 14 -S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 , or CH2OC(=O)R 14 and; R 5 However, these are H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 6 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 7 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R8 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; G, OR 10 , SR 10 SOR 10 , or SO2R 10 and; R 9 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 10 However, these are H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C7 haloalkoxyalkyl, benzyl, or C4-C7 alkylcycloalkyl; R 11 However, it is H or C1-C7 alkyl; R 12 However, it is H or C1-C7 alkyl; Each R 13 and R 14 However, independently, they are H, C1-C7 haloalkyl, or C1-C7 alkyl; R f It is a C1-C3 haloalkyl group; compound.

[0174] Embodiment B1. R 1 However, it is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl; R 2However, it is H, Me, F, Cl, or CN; R 3 However, it is H, Me, F, Cl, -CN, OMe, or CF3; R 4 is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-t-Bu, CH2OCO-n-Bu, CH2OCO-c-hexyl, CH2OCO-c-pentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-i-Bu, CH2OCOMe, CH2OCO-sec-Bu, CH2OCO-n-Pr and CH2OCO-i-Pr, or (C=O)SMe; R 5 However, it is H, C4-C7 cycloalkylalkyl, or C2-C7 alkoxyalkyl; R 6 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 7 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; G, OR 10 or SR 10 and; R 9 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 10 However, these are C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C2-C4 cyanoalkyl, C3-C7 alkylthioalkyl, or C4-C7 alkylcycloalkyl; The compound of Embodiment B.

[0175] Embodiment B2. R 1However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH2OCOR 14 , or -S(O)2R 14 and; R 5 H is; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; G is OR 10 and; R 9 However, it is H, Me, or OMe; R 10 However, it is H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, or C4-C7 alkylcycloalkyl; Compound of Embodiment B1.

[0176] Embodiment B3. R 1 However, it is H, Me, F, Cl, Br, or cyclopropyl; R 4 However, it is H, CH2OCO-t-Bu, or SO2CF3; R 8 H is; R 9 H is; R 10 However, these are C2-C6 alkenyls, C2-C6 alkynyls, or C3-C7 cycloalkyls; Compound of Embodiment B2.

[0177] Embodiment C. A compound of Formula 1 as described in the summary of the disclosure, Q is O; R 1However, these are H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and C1-C7 haloalkyl; R 2 However, it is H, C1-C7 alkyl, halogen, or CN; R 3 However, it is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R 4 However, H, C(=O)R 14 -C(=S)R 14 , -CO2R 14 -C(=O)SR 14 -S(O)2R 14 , C(=O)NR 13 R 14 -S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 , or CH2OC(=O)R 14 and; R 5 However, these are H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 6 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 7 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; G, OR 10 , SR 10 SOR 10 , or SO2R 10 and; R 10 However, these are H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C7 haloalkoxyalkyl, benzyl, or C4-C7 alkylcycloalkyl; R 11 However, it is H or C1-C7 alkyl; R 12 However, it is H or C1-C7 alkyl; Each R 13 and R 14 However, independently, they are H, C1-C7 haloalkyl or C1-C7 alkyl; R f It is a C1-C3 haloalkyl group; compound.

[0178] Embodiment C1. R 1 However, it is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3 However, it is H, Me, F, Cl, -CN, OMe, or CF3; R 4is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-t-Bu, CH2OCO-n-Bu, CH2OCO-c-hexyl, CH2OCO-c-pentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-i-Bu, CH2OCOMe, CH2OCO-sec-Bu, CH2OCO-n-Pr and CH2OCO-i-Pr, or (C=O)SMe; R 5 However, it is H, C4-C7 cycloalkylalkyl, or C2-C7 alkoxyalkyl; R 6 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 7 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; G, OR 10 or SR 10 and; R 10 However, these are C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C2-C4 cyanoalkyl, C3-C7 alkylthioalkyl, benzyl, or C4-C7 alkylcycloalkyl; The compound of Embodiment C.

[0179] Embodiment C2. R 1 However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH2OCOR 14 , or -S(O)2R14 and; R 5 H is; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; G is OR 10 and; R 10 However, these are C2-C6 alkenyls, C2-C6 alkynyls, C3-C7 cycloalkyls, C4-C7 cycloalkylalkyls, C4-C7 halocycloalkylalkyls, or C4-C7 alkylcycloalkyls; Compound of Embodiment C1.

[0180] Embodiment C3. R 1 However, it is H, Me, F, Cl, Br, or cyclopropyl; R 4 However, it is H, CH2OCO-t-Bu, or S(O)2CF3; R 8 H is; R 10 However, these are C2-C6 alkenyls, C2-C6 alkynyls, or C3-C7 cycloalkyls; Compound of Embodiment C2.

[0181] Embodiment C4. R 1 That is Me; R 3 That is Me; R 4 H is; R 6 H is; R 7 H is; R 10 is cyclopropyl, cyclobutyl, cyclopentyl, allyl, or propargyl; Compound of Embodiment C3.

[0182] A compound of Formula 1 described in the summary of the disclosure in Embodiment D, R 1 However, these are H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and C1-C7 haloalkyl; R 2 However, it is H, C1-C7 alkyl, halogen, or CN; R 3 However, it is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R 4 However, H, C(=O)R 14 -C(=S)R 14 , -CO2R 14 -C(=O)SR 14 -S(O)2R 14 , C(=O)NR 13 R 14 -S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 , or CH2OC(=O)R 14 and; R 6 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 7 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; G and R 5 But together N-OR 15 It forms; R 11 However, it is H or C1-C7 alkyl; R 12 However, it is H or C1-C7 alkyl; R 13 and R 14 However, independently, they are H, C1-C7 haloalkyl, or C1-C7 alkyl; R f It is a C1-C3 haloalkyl; R 15 However, these are H, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C4-C7 cycloalkylalkyl; compound.

[0183] Embodiment D1. R 1 However, it is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3 However, it is H, Me, F, Cl, -CN, OMe, or CF3; R 4 is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-t-Bu, CH2OCO-n-Bu, CH2OCO-c-hexyl, CH2OCO-c-pentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-i-Bu, CH2OCOMe, CH2OCO-sec-Bu, CH2OCO-n-Pr and CH2OCO-i-Pr, or (C=O)SMe; R 6 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 7 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; Compound of Embodiment D.

[0184] Embodiment D2. R 1 However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH2OCOR 14 , or -S(O)2R 14 and; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; Compound of Embodiment D1.

[0185] Embodiment D3. R 1 However, it is H, Me, F, Cl, Br, or cyclopropyl; R 4 However, it is H, CH2OCO-t-Bu, or SO2CF3; R 8 H is; Compound of Embodiment D2.

[0186] Embodiment D4. R 1 That is Me; R 3 That is Me; R 4 H is; R 6 H is; R7 H is; R 15 However, these are H, Me, Et, CH2CH=CH2, or CH2C≡CH; Compound of Embodiment D3.

[0187] Embodiment D5. A compound from any one of Embodiments D to D4, wherein Q is a direct bond.

[0188] Embodiment P1. Compounds selected from Formula 1, all stereoisomers thereof, N-oxides, and salts. [ka] (In the formula, R 1 These are H, C1-C7 alkyl, halogen, CN, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, or C2-C7 haloalkoxyalkyl; R 2 These are H, C1-C7 alkyl, halogen, CN, C1-C7 haloalkyl, C1-C7 alkoxy, or C1-C5 alkylthio; R 3 These are H, C1-C7 alkyl, halogen, CN, C2-C6 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, or C2-C7 haloalkoxyalkyl; R 4 H, C(=O)R 14 -C(=S)R 14 , -CO2R 14 -C(=O)SR 14 -S(O)2R 14 , C(=O)NR13 R 14 -S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 , or CH2OC(=O)R 14 ; or propargyl, allyl, or benzyl; R 5 These are H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C3-C7 alkylthioalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 6 These are H, C1-C7 alkyl, halogen, CN, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 haloalkoxyalkyl, or C4-C7 alkylcycloalkyl; R 7 These are H, C1-C7 alkyl, halogen, CN, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 haloalkoxyalkyl, or C4-C7 alkylcycloalkyl; R8 These are H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; Q is CHR 9 , O, or direct bond; R 9 These are H, C1-C7 alkyl, halogen, CN, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C7 haloalkoxyalkyl, or C4-C7 alkylcycloalkyl; G is OR 10 , SR 10 SOR 10 , or SO2R 10 and; R 10 These are H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, and C3-C 10 Alkenylalkyl, C3~C 10 Alkynylalkyl, C4~C 10 Alkylalkenylalkyl, C4~C 10Alkylalkynylalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C4 cyanoalkyl, C4-C7 alkylcycloalkyl, C1-C6 nitroalkyl, C3-C6 alkylcarboalkyl, C3-C6 alkoxycarboalkyl, or C3-C6 alkylcarboalkoxy; or R 10 teeth, [ka] Selected from the group consisting of, R 11 These are H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 12 These are H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, or C7 haloalkyl; Each R 13 and R 14 These are independently H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkylalkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl, C4-C7 alkylcycloalkyl, Ph, or benzyl; R f These are C1-C7 haloalkyl groups; G and R 8 It can be linked to any ring carbon having available valence, the ring being a cyclic amide ring represented by formula 1; Each R 11 or R 12 It can be linked to any ring carbon having available valence, and the ring is the above R 10 -1~R 10 (As shown by -16).

[0189] Embodiment P2. Q is a direct connection; R 1 However, these are H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and C1-C7 haloalkyl; R 2 However, it is H, C1-C7 alkyl, halogen, or CN; R 3 However, it is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R 4 However, H, C(=O)R 14 -C(=S)R 14 , -CO2R 14 -C(=O)SR 14 -S(O)2R 14 , C(=O)NR 13 R 14 -S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 , or CH2OC(=O)R 14 and; R 5 However, these are H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 6However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 7 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; G, OR 10 , SR 10 SOR 10 , or SO2R 10 and; R 10 However, H, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C3-C 10 Alkenylalkyl, C3~C 10 Alkynylalkyl, C4~C 10 Alkylalkenylalkyl, C4~C 10 These are alkylalkynylalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, or C4-C7 alkylcycloalkyl; R 11 However, it is H or C1-C7 alkyl; R 12 However, it is H or C1-C7 alkyl; R 13 and R 14 However, independently, they are H, C1-C7 haloalkyl, or C1-C7 alkyl; R f It is a C1-C3 haloalkyl group; Compound of Embodiment P1.

[0190] Embodiment P3. R 1 However, it is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3 However, it is H, Me, F, Cl, -CN, OMe, or CF3; R 4 is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-t-Bu, CH2OCO-n-Bu, CH2OCO-c-hexyl, CH2OCO-c-pentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-i-Bu, CH2OCOMe, CH2OCO-sec-Bu, CH2OCO-n-Pr and CH2OCO-i-Pr, or (C=O)SMe; R 5 However, it is H, C4-C7 cycloalkylalkyl, or C2-C7 alkoxyalkyl; R 6 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 7 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; G, OR 10 or SR 10 and; R 10However, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C3-C 10 Alkenylalkyl, C3~C 10 Alkynylalkyl, C4~C 10 Alkylalkenylalkyl, C4~C 10 These are alkylalkynylalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C3-C7 alkylthioalkyl, or C4-C7 alkylcycloalkyl; Compound of Embodiment P2.

[0191] Embodiment P4. R 1 However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH2OCOR 14 , or -S(O)2R 14 and; R 5 H is; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; G is OR 10 and; R 10 However, C3-C7 cycloalkyl, C3-C 10 Alkenylalkyl, C3~C 10 It is an alkynylalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; Compound of Embodiment P3.

[0192] Embodiment P5. R1 However, it is H, Me, F, Cl, Br, or cyclopropyl; R 4 However, it is H, CH2OCO-t-Bu, or SO2CF3; R 8 H is; R 10 However, C3-C7 cycloalkyl, C3-C 10 Alkenylalkyl, or C3-C 10 It is an alkynylalkyl; Compound of Embodiment P4.

[0193] Embodiment P6. R 1 That is Me; R 3 That is Me; R 4 H is; R 6 H is; R 7 H is; R 10 However, these are cyclopropyl, cyclobutyl, cyclopentyl, allyl, or propargyl; Compound of Embodiment P5.

[0194] Embodiment P7. Q is CHR 9 and; R 1 However, these are H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and C1-C7 haloalkyl; R 2 However, it is H, C1-C7 alkyl, halogen, or CN; R 3 However, it is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R 4 However, H, C(=O)R 14 -C(=S)R 14 , -CO2R 14 -C(=O)SR 14 -S(O)2R 14, C(=O)NR 13 R 14 -S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 , or CH2OC(=O)R 14 and; R 5 However, these are H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 6 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 7 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; G, OR 10 , SR 10 SOR 10 , or SO2R 10 and; R 9However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 10 However, alkynylalkyl, C4~C 10 Alkylalkenylalkyl, C4~C 10 These are alkylalkynylalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, or C4-C7 alkylcycloalkyl; R 11 However, it is H or C1-C7 alkyl; R 12 However, it is H or C1-C7 alkyl; R 13 and R 14 However, independently, they are H, C1-C7 haloalkyl, or C1-C7 alkyl; R f It is a C1-C3 haloalkyl group; Compound of Embodiment P6.

[0195] Embodiment P8. R 1 However, it is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3 However, it is H, Me, F, Cl, -CN, OMe, or CF3; R 4is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-t-Bu, CH2OCO-n-Bu, CH2OCO-c-hexyl, CH2OCO-c-pentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-i-Bu, CH2OCOMe, CH2OCO-sec-Bu, CH2OCO-n-Pr and CH2OCO-i-Pr, or (C=O)SMe; R 5 However, it is H, C4-C7 cycloalkylalkyl, or C2-C7 alkoxyalkyl; R 6 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 7 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; G, OR 10 or SR 10 and; R 9 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 10 However, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C3-C 10 Alkenylalkyl, C3~C 10 Alkynylalkyl, C4~C 10 Alkylalkenylalkyl, C4~C 10 These are alkylalkynylalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C3-C7 alkylthioalkyl, or C4-C7 alkylcycloalkyl; Compound of Embodiment P7.

[0196] Embodiment P9. R 1However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH2OCOR 14 , or -S(O)2R 14 and; R 5 H is; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; G is OR 10 and; R 9 However, it is H, Me, or OMe; R 10 However, C3-C7 cycloalkyl, C3-C 10 Alkenylalkyl, C3~C 10 It is an alkynylalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; Compound of Embodiment P8.

[0197] Embodiment P10. R 1 However, it is H, Me, F, Cl, Br, or cyclopropyl; R 4 However, it is H, CH2OCO-t-Bu, or SO2CF3; R 8 H is; R 9 H is; R 10 However, C3-C7 cycloalkyl, C3-C 10 Alkenylalkyl, or C3-C 10 It is an alkynylalkyl; Compound of Embodiment P9.

[0198] Embodiment P11. Q is O; R 1 However, these are H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, and C1-C7 haloalkyl; R 2 However, it is H, C1-C7 alkyl, halogen, or CN; R 3 However, it is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R 4 However, H, C(=O)R 14 -C(=S)R 14 , -CO2R 14 -C(=O)SR 14 -S(O)2R 14 , C(=O)NR 13 R 14 -S(O)2NR 13 R 14 CH2OC(=O)OR 14 CH2OC(=O)NR 13 R 14 , or CH2OC(=O)R 14 and; R 5 However, these are H, C2-C6 alkenyl, C2-C7 haloalkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; R 6 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 7 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; G, OR 10 , SR 10 SOR 10 , or SO2R 10 and; R 10 However, alkynylalkyl, C4~C 10 Alkylalkenylalkyl, C4~C 10 Alkylalkynylalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C4-C7 alkylcycloalkylalkyl, C1-C7 haloalkoxy, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C1-C7 haloalkyl, C2-C7 haloalkenyl, C3-C7 alkylthioalkyl, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, or C4-C7 alkylcycloalkyl; R 11 However, it is H or C1-C7 alkyl; R 12 However, it is H or C1-C7 alkyl; R 13 and R 14 However, independently, they are H, C1-C7 haloalkyl, or C1-C7 alkyl; R f It is a C1-C3 haloalkyl group; Compound of Embodiment P1.

[0199] Embodiment P12. R 1 However, it is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3However, it is H, Me, F, Cl, -CN, OMe, or CF3; R 4 is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-t-Bu, CH2OCO-n-Bu, CH2OCO-c-hexyl, CH2OCO-c-pentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-i-Bu, CH2OCOMe, CH2OCO-sec-Bu, CH2OCO-n-Pr and CH2OCO-i-Pr, or (C=O)SMe; R 5 However, it is H, C4-C7 cycloalkylalkyl, or C2-C7 alkoxyalkyl; R 6 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; R 7 However, it is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, or C1-C7 haloalkoxy; R 8 However, it is H, C1-C7 alkyl, or C1-C7 alkoxy; G, OR 10 or SR 10 and; R 10 However, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C3-C 10 Alkenylalkyl, C3~C 10 Alkynylalkyl, C4~C 10 Alkylalkenylalkyl, C4~C 10 These are alkylalkynylalkyl, C4-C7 alkylcycloalkyl, C4-C7 cycloalkylalkyl, C4-C7 halocycloalkylalkyl, C5-C7 alkylcycloalkylalkyl, C2-C7 alkoxyalkyl, C2-C4 cyanoalkyl, C3-C7 alkylthioalkyl, or C4-C7 alkylcycloalkyl; Compound of Embodiment P11.

[0200] Embodiment P13. R 1However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH2OCOR 14 , or -S(O)2R 14 and; R 5 H is; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; G is OR 10 and; R 10 However, C3-C7 cycloalkyl, C3-C 10 Alkenylalkyl, C3~C 10 It is an alkynylalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkoxyalkyl, or C4-C7 alkylcycloalkyl; Compound of Embodiment P12.

[0201] Embodiment P14. R 1 However, it is H, Me, F, Cl, Br, or cyclopropyl; R 4 However, it is H, CH2OCO-t-Bu, or SO2CF3; R 8 H is; R 10 However, C3-C7 cycloalkyl, C3-C 10 Alkenylalkyl, or C3-C 10 It is an alkynylalkyl; Compound of Embodiment P13.

[0202] Embodiment P15. R 1 That is Me; R 3 That is Me; R4 H is; R 6 H is; R 7 H is; R 10 However, these are cyclopropyl, cyclobutyl, cyclopentyl, allyl, or propargyl; Compound of Embodiment P14.

[0203] Specific embodiments include compounds of Formula 1 selected from the following group: [ka]

[0204] The present invention also relates to a method for controlling unwanted vegetation, comprising applying a herbicidally effective amount of the compound of the present invention (for example, as a composition described herein) to a vegetation habitat. Notable embodiments of the method of use involve the compounds of the embodiments described above. The compounds of the present invention are particularly useful for the selective control of weeds in crops such as wheat, barley, maize, soybeans, sunflowers, cotton, rapeseed, and rice, as well as specialty crops such as sugarcane, citrus fruits, fruit, and nut crops.

[0205] Another embodiment worth noting is the herbicidal composition of the present invention, which contains the compounds of the above embodiments.

[0206] The present invention further comprises herbicide mixtures including: (a) compounds selected from Formula 1, their N-oxides, and salts; and (b) at least one further active ingredient, selected from: (b1) photosystem II inhibitors; (b2) acetohydroxy acid synthase (AHAS) inhibitors; (b3) acetyl-CoA carboxylase (ACCase) inhibitors; (b4) auxin mimetic; (b5) 5-enol-pyruvir schimate-3-phosphate (EPSP) synthase inhibitors; (b6) photosystem I electron diverters. (b) diverter, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long-chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoendesaturase (PDS) inhibitors, (b12) 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisic acid soranesyltransferase (HST) inhibitors, (b14) Cellulose biosynthesis inhibitors, (b15) Other herbicides (including mitotic disruptors, organoarsenic compounds, ashrum, bromobutide, simmethyline, cumylon, dazomet, diphenzocort, dimuron, etobenzanide, flurenol, hosamine, hosamine-ammonium, hydantocidin, metam, methyldimuron, oleic acid, oxadichromephone, pelargonic acid, and bilibuticarb), (b16) Herbicide safeners, and salts of compounds (b1) to (b16).

[0207] "Photosystem II inhibitors" (b1) are Q B - Bonding niche (Q B - A compound that binds to the D-1 protein at the binding niche, thereby Q in the thylakoid membrane of chloroplasts. A From Q B It blocks electron transport to chloroplasts. Electrons blocked from the pathway through photosystem II are transported through a series of reactions to form toxic compounds that disrupt the cell membrane, leading to chloroplast swelling, membrane leakage, and ultimately cell destruction.B - The binding niche has three different binding sites: Binding site A binds to triazines such as atrazine, triazinones such as hexazinone, and uracil such as bromacil; Binding site B binds to phenylurea such as diurone; and Binding site C binds to benzothiadiazoles such as bentazone, nitriles such as bromoxynil, and phenylpyridazine such as pyridate. Examples of photosystem II inhibitors include: ametrine, amicarbazone, atrazine, bentazone, bromacil, bromophenoxime, bromoxynil, chlorbromulone, chloridazone, chlorotolurone, chloroxylurone, cumilone, cyanazine, dimuron, desmedifam, desmethrin, dimeflon, dimethametrin, diurone, ethidimulone, phenurone, fluomethron, hexazinone, ioxynil Isoproturone, Isourone, Renasil, Linurone, Metamitron, Metabenzthiazulon, Metobromulone, Methoxyurone, Metrivudine, Monolyneuron, Nebulon, Pentanocrol, Fenmedifam, Prometon, Promethrin, Propanil, Propazine, Pyridafol, Piridate, Siderone, Simazine, Simetrin, Tebuthiurone, Terbasil, Terbumeton, Terbutyrazine, Terbutrin, and Trietazine.

[0208] "AHAS inhibitors" (b2) are compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and kill plants by inhibiting the production of branched-chain aliphatic amino acids such as valine, leucine, and isoleucine, which are necessary for protein synthesis and cell growth.Examples of AHAS inhibitors include: amidesulfuron, azimsulfuron, bensulfuron-methyl, bispiribac-sodium, chloransulam-methyl, chlorimulon-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, etamethosulfuron-methyl, ethoxysulfuron, flurazasulfuron, florasulam, flucarbazone-sodium, flumethoslam, flupyrsulfuron-methyl, flupyrsulfuron-sodium, foramsulfuron, and halosulfuron. -Methyl, Imazametabuns-Methyl, Imazamox, Imazapick, Imazapyr, Imazakine, Imazetapir, Imazosulfuron, Iodosulfuron-Methyl (containing sodium salt), Iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)amino]carbonyl]benzenesulfonamide), Mezosulfuron-Methyl, Metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazine-3-yl)-N-[[(4,6-dimethoxy (C-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), Methoslam, Methosulfuron-methyl, Nicosulfuron, Oxasulfuron, Penoxlam, Primisulfuron-methyl, Propoxycarbazone-sodium, Propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), Prosulfuron, Pyrazosulfuron-ethyl, Pyribenzoxime, Pyriph Thalide, pyriminovac-methyl, pyrithiovac-sodium, limsulfuron, sulfomethuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazine-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenulon-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl, and tritosulfuron.

[0209] "ACCase inhibitors" (b3) are compounds that inhibit the acetyl-CoA carboxylase enzyme, which acts as a catalyst in the initial stages of lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes; without them, new cells cannot be produced. The inhibition of acetyl-CoA carboxylase and the subsequent lack of lipid production lead to a loss of cell membrane integrity, particularly in active growth areas such as meristems. Ultimately, shoot and rhizome growth ceases, and the meristem of shoots and buds of rhizomes begin to wither. Examples of ACCase inhibitors include: alloxidime, butroxidime, cretodyme, clodinahop, cycloxidime, cyhalofop, diclohop, phenoxaprop, fluazihop, haloxyhop, pinoxadene, propoxoxidime, propaxifop, quizalohop, cethoxidime, tepraloxidime, and tralcoxidime (including divided forms such as phenoxaprop-P, fluazihop-P, haloxyhop-P, and quizalohop-P, and ester forms such as clodinahop-propargyl, cyhalofop-butyl, diclohop-methyl, and phenoxaprop-P-ethyl).

[0210] Auxin is a plant hormone that regulates growth in many plant tissues. "Auxin mimics" (b4) are compounds that mimic the plant growth hormone auxin, leading to uncontrolled and disordered growth, and in sensitive species, can result in plant death. Examples of auxin mimics include: aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralide, benazoline-ethyl, chloramben, crasifos, clomeprop, clopyralide, dicamba, 2,4-D, 2,4-DB, dicloprop, fluroxypyr, harauxifen (4-amino-3-chloro-6-(4-chloro- 2-Fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), halaxifen-methyl(4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarbonate methyl), MCPA, MCPB, mecoprop, picrolam, quinchlorac, kinmelac, 2,3,6-TBA, triclopyr, and 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate methyl.

[0211] "EPSP synthase inhibitors" (b5) are compounds that inhibit 5-enol-pyruvirschimate-3-phosphate synthase, an enzyme involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan, and phenylalanine. EPSP inhibitory herbicides are readily absorbed through the leaves of plants and translocated to the meristem through the phloem. Glyphosate is a relatively non-selective post-emergence herbicide belonging to this group. Glyphosate includes esters and salts of, for example, ammonium, isopropylammonium, potassium, sodium (including sesquisodium), and trimethium (also known as sulfosate).

[0212] "Photosystem I electron diverters" (b6) are compounds that accept electrons from photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are highly reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This disrupts the integrity of the cell membrane, resulting in "leakage" in cells and organelles, causing leaves to wilt and dry out rapidly, and ultimately leading to plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.

[0213] "PPO inhibitors" (b7) are compounds that inhibit the enzyme protoporphyrinogen oxidase, causing the rapid production of highly active compounds in plants, which disrupt cell membranes and leak cellular fluid. Examples of PPO inhibitors include: acifluorphen-sodium, azaphenidine, benzfenzizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, clomethoxyfen, synidone-ethyl, fluazolate, flufenpyr-ethyl, flumicrolac-pentyl, flumioxazine, fluoroglycofen-ethyl, fluthiaset-methyl, homesafen, halosaphen, lactofen, oxaziargyl, oxadiazone, oxyfluorphen, pentoxazone, profluazole, pyraclonil, and pyraflufen-ethyl. Saflufenacil, sulfenthrazone, thidiadimine, trifludimoxazine (dihydro-1,5-dimethyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyne-1-yl)-2H-1,4-benzoxazine-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione), and thiafenacil (methyl N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate).

[0214] "GS inhibitors" (b8) are compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia to glutamine. Consequently, ammonia accumulates, and glutamine levels decrease. The damage to plants is likely due to a combination of the toxicity of ammonia and the deficiency of amino acids required in other metabolic processes. Examples of GS inhibitors include: glufosinate and its esters and salts, e.g., glufosinate-ammonium and other phosphinotricin derivatives, glufosinate-P ((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid), and viranaphos.

[0215] "VLCFA elongase inhibitors" (b9) are herbicides with a wide range of chemical structures that inhibit elongase. Elongase is one of the enzymes located inside or near chloroplasts and is involved in the biosynthesis of VLCFAs. In plants, very long-chain fatty acids are the main components of hydrophobic polymers, preventing drying on the leaf surface and providing stability to pollen grains. Examples of such herbicides include: acetochlor, alachlor, anirophos, butachlor, cafenstrol, dimetachlor, dimethenamide, diphenamide, phenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanophan, mefenacet, metazachlor, metrachlor, naproanilide, napropamide, napropamide-M((2R)-N,N-diethyl-2-(1-naphthalenyloxy)propanamide), petoxamide, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and tenylchlor (including divided forms such as S-methochlor, as well as chloroacetamide and oxyacetamide).

[0216] Auxin transport inhibitors (b10) are chemical substances that inhibit auxin transport in plants, for example, by binding to auxin transport proteins. Examples of auxin transport inhibitors include: diflufenzopyr and naptalam (also known as N-(1-naphthyl)phthalamidic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid).

[0217] "PDS inhibitors" (b11) are compounds that inhibit the carotenoid biosynthesis pathway in the phytoendesaturase step. Examples of PDS inhibitors include: beflubutamide, diflufenican, flulidone, flurochloridone, flurutamon, norflurzone, and picolinafene.

[0218] HPPD inhibitors (b12) are chemical substances that inhibit the biosynthesis of 4-hydroxyphenylpyruvate dioxygenase. Examples of HPPD inhibitors include: benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]octo-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3 -Cyclohexanedione), isoxachlortol, isoxaflutol, mesotrione, pyrasulfol, pyrazolinate, pyrazoxyfen, sulcotrione, tefuryltrione, tenbotrione, tolpyrate (1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethylmethyl carbonate), topramezone, 5-chloro-3-[(2-hydroxy [-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydro [Xy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide, and 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.

[0219] "HST inhibitors" (b13) disrupt the plant's ability to convert homogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include haloxydin, pyricrol, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridine-2(1H)-one, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazine-6(5H)-one, and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.

[0220] HST inhibitors also include compounds of formulas A and B: [ka] In the formula, R d1 is H, Cl, or CF3; R d2 is H, Cl, or Br; R d3 is H or Cl; R d4 is H, Cl, or CF3; R d5 is CH3, CH2CH3, or CH2CHF2; and R d6 is OH, or -OC(=O)-i-Pr; and R e1 is H, F, Cl, CH3, or CH2CH3; R e2 is H, or CF3; R e3 is H, CH3, or CH2CH3; R e4 is H, F, or Br; R e5 is Cl, CH3, CF3, OCF3, or CH2CH3; R e6 is H, CH3, CH2CHF2, or C≡CH; R e7 is OH, -OC(=O)Et, -OC(=O)-i-Pr, or -OC(=O)-t-Bu; and A e8 It is either N or CH.

[0221] Cellulose biosynthesis inhibitors (b14) inhibit cellulose biosynthesis in certain plants. They are most effective when applied to young plants before or shortly after budding, or to rapidly growing plants. Examples of cellulose biosynthesis inhibitors include: chlorthiamide, diclobenyl, phlopoxam, and indadiphram (N 2 -[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben, and triaziphram.

[0222] "Other herbicides" (b15) include, for example, herbicides that function in various modes of action, such as: mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl), organoarsenic compounds (e.g., DSMA and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors, and cell wall biosynthesis inhibitors. Other herbicides also include those whose mode of action is unknown, or which do not fall into any of the specific categories listed in (b1) to (b14), or which act in combination of the modes listed above. Other examples of herbicides include acronifen, asharam, amitorol, bromobutide, scinmethilin, cromazon, cumylon, cyclopyrimolate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholine carboxylate), dimuron, diphenzocoat, etobenzanide, fluomethron, flurenol, hosamin, hosamin-ammonium, dazomet, dimuron, ipfencarbazone (1-( Examples include 2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide), metam, methyl dimuron, oleic acid, oxadiclomefone, pelargonic acid, pyributicarb, and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.

[0223] "Other herbicides" (b15) also contain the compound of formula (b15A), [ka] During the ceremony, R 12’ These are H, C1-C6 alkyl, C1-C6 haloalkyl, or C4-C8 cycloalkyl; R 13’ is H, C1-C6 alkyl, or C1-C6 alkoxy; Q 1 This is a ring system that is optionally substituted from the group consisting of phenyl, thienyl, pyridinyl, benzodioxolyl, naphthalenyl, benzofuranyl, furanyl, benzothiophenyl, and pyrazolyl, where, when substituted, the ring system has 1 to 3 R 14’ It has been replaced with; Q 2 This is a ring system that is optionally substituted from the group consisting of phenyl, pyridinyl, benzodioxolyl, pyridinonyl, thiadiazolyl, thiazolyl, and oxazolyl, where, when substituted, the ring system has 1 to 3 R 15’ It has been replaced with; Each R 14’ These are independently halogens, C1-C6 alkyls, C1-C6 haloalkyls, C1-C6 alkoxys, C1-C6 haloalkoxys, C3-C8 cycloalkyls, cyanos, C1-C6 alkylthios, C1-C6 alkylsulfinyls, C1-C6 alkylsulfonyls, SF5, and NHR. 17 ; or 1 to 3 R 16 Phenyl substituted with any choice of R; or 1 to 3 R 16 It is pyrazolyl which is optionally substituted; Each R 15’ These are independently halogens, C1-C6 alkyls, C1-C6 haloalkyls, C1-C6 alkoxys, C1-C6 haloalkoxys, cyanos, nitros, C1-C6 alkylthios, C1-C6 alkylsulfinyls, and C1-C6 alkylsulfonyls; Each R 16’ These are independently halogens, C1-C6 alkyls, or C1-C6 haloalkyls; R 17’ These are C1-C4 alkoxycarbonyl groups.

[0224] In one embodiment, “other herbicides” (b15) also include a compound of formula (b15A), R 12’ Preferably, R is H or C1-C6 alkyl; more preferably, 12’ is H or methyl. Preferably, R 13’ is H. Preferably, Q 1 The ring is a phenyl ring or a pyridinyl ring, and each ring has 1 to 3 R atoms. 14’ It is replaced by; more preferably, Q 1 This is 1-2 R 14’ It is a phenyl ring substituted with Q. Preferably, Q 2 This is 1 to 3 R 15’ A phenyl ring substituted with; more preferably, Q 2 This is 1-2 R 15’ A phenyl ring substituted with R. Preferably, each R 14’ R is independently a halogen, a C1-C4 alkyl, a C1-C3 haloalkyl, a C1-C3 alkoxy, or a C1-C3 haloalkoxy; more preferably, each R 14’ R is independently chloro, fluoro, bromo, C1-C2 haloalkyl, C1-C2 haloalkoxy, or C1-C2 alkoxy. Preferably, each R 15’ R is independently a halogen, a C1-C4 alkyl, or a C1-C3 haloalkoxy; more preferably, each R 15’ These are independently chloro, fluoro, bromo, C1-C2 haloalkyl, C1-C2 haloalkoxy, or C1-C2 alkoxy.

[0225] Specific examples of preferred "other herbicides" (b15) include any of the following (b15A-1) to (b15A-15): [ka] [ka] [ka]

[0226] "Other herbicides" (b15) also include the compound of formula (b15B), [ka] During the ceremony, R 18’ These are H, C1-C6 alkyl, C1-C6 haloalkyl, or C4-C8 cycloalkyl; Each R 19’ These are independently halogens, C1-C6 haloalkyls, or C1-C6 haloalkoxys; p is an integer, either 0, 1, 2, or 3; Each R 20’ These are independently halogens, C1-C6 haloalkyls, or C1-C6 haloalkoxys; q is an integer of 0, 1, 2, or 3.

[0227] In one embodiment, “other herbicides” (b15) also include a compound of formula (b15B), R 18 Preferably, is H, methyl, ethyl, or propyl; more preferably, R 18 is H or methyl; most preferably R 18 is H. Preferably, each R 19 R is independently chloro, fluoro, C1-C3 haloalkyl or C1-C3 haloalkoxy; more preferably each R 19 R is independently chloro, fluoro, C1-fluoroalkyl (i.e., fluoromethyl, difluoromethyl, or trifluoromethyl) or C1-fluoroalkoxy (i.e., trifluoromethoxy, difluoromethoxy, or fluoromethoxy). Preferably, each R 20R is independently chloro, fluoro, C1-haloalkyl, or C1-haloalkoxy; more preferably each R 20 These are independently chloro, fluoro, C1-fluoroalkyl (i.e., fluoromethyl, difluoromethyl, or trifluoromethyl) or C1-fluoroalkoxy (i.e., trifluoromethoxy, difluoromethoxy, or fluoromethoxy).

[0228] Particularly preferred "other herbicides" (b15) include one of the following (b15B-1) to (b15B-19). [ka] [ka] [ka]

[0229] In another embodiment, “other herbicides” (b15) also includes a compound of formula (b15C), [ka] In the formula, R 1’ is Cl, Br, or CN; R 2’ These are C(=O)CH2CH2CF3, CH2CH2CH2CH2CF3, or 3-CHF2-isoxazole-5-yl.

[0230] Herbicide toxicity mitigators (b16) are substances added to herbicide formulations to eliminate or reduce the phytotoxic effects of the herbicide on certain crops. These compounds protect crops from herbicide damage but typically do not prevent the herbicide from controlling undesirable vegetation. Examples of herbicide toxicity mitigators include, but are not limited to, the following: benoxacol, croquintoset-mexyl, cumylon, siomethrinyl, cyprosulfamide, dimuron, dichlormid, dicyclonone, dietholate, dimepiperate, fenchlorazole-ethyl, fenchlorim, flurazole, fluxofenim, flirazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxavethrinyl, N-(aminocarbonyl)-2-methylbenzenesulfonamide, and N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone, and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide.

[0231] The compounds of Formula 1 can be prepared using one or more of the following methods and variations described in Schemes 1 to 13: G, Q, X, R in the compounds of Formulas 1 to 19 below. 1 ~R 10 , and R f The definition of is as defined above in the summary of this disclosure, unless otherwise stated. The compounds of formulas 1a, 1b, 1c, 1d, 3a, 4a, 4b, 4c, 5a, and 5b are various subsets of the compounds of formulas 1, 3, 4, and 5, and all substituents of formulas 1a, 1b, 1c, 1d, 3a, 4a, 4b, 4c, 5a, and 5b are as defined above for formula 1, unless otherwise stated in the disclosure including the scheme.

[0232] As shown in Scheme 1, the compound of formula 1a (i.e., R 4 The compound of formula 1 (where is H) is prepared in the presence of a suitable base in a suitable solvent, including but not limited to tetrahydrofuran, acetonitrile, toluene, diethyl ether, dioxane, dichloromethane, or N,N-dimethylformamide, at a temperature generally ranging from 0°C to ambient temperature, with 1 equivalent (or slightly more than 1 equivalent) of formula R f SO2Cl haloalkylsulfonyl chloride or the corresponding formula R f It can be prepared by the reaction of (SO2)2O with a haloalkylsulfonyl anhydride. Some examples of suitable bases can be pyridine, triethylamine, Hünig base, or potassium carbonate. Alternatively, the bis-sulfonamide of formula 1b (i.e., R 4 SO2R f And R f The compound of formula 1 (where is a haloalkyl) contains 2 equivalents (or an excess amount greater than 2.0 equivalents) of aniline of formula 2. f SO2Cl haloalkylsulfonyl chloride or formula R f (SO2)2O can be obtained by reacting the corresponding haloalkylsulfonyl anhydride with the same reaction conditions as described above. The corresponding mono-sulfonamide of formula 1a can be easily obtained by treating the bis-sulfonamide of formula 1b with an excess aqueous base, followed by neutralization or acidification with an acid. Preferred conditions for this hydrolysis are an aqueous solution of sodium hydroxide or potassium hydroxide, followed by neutralization or acidification with concentrated hydrochloric acid or an aqueous hydrochloric acid solution, which is usually used with an optional cosolvent such as methanol, ethanol, dioxane, or tetrahydrofuran. [ka]

[0233] Substituted anilines of formula 2 can be readily obtained by hydrogenation of nitrobenzene of formula 3 under conditions including, but not limited to, catalytic hydrogenation with 5-10% palladium metal on carbon or platinum oxide in a solvent such as methanol, ethanol, or ethyl acetate under a hydrogen atmosphere. This reaction can generally be carried out in a Parr Hydrogenator. Alternatively, reduction of the nitro group can be achieved with activated zinc metal in acetic acid, stannous chloride in aqueous hydrochloric acid, metallic iron in acetic acid, aqueous alcohol, or in an aqueous ethyl acetate mixture with ammonium chloride (i.e., 3 equivalents of ammonium chloride and Fe in aqueous ethanol), or sodium borohydride in methanol in the presence of NiAC2-4H2O (see J.Am.Chem.Soc., 2005, 119). [ka]

[0234] The intermediate of formula 3 can be obtained by copper-mediated coupling of a meta-bromo or meta-iodosubstituted nitrobenzene of formula 4a or 4b (wherein X is bromine for 4a and iodine for 4b) with a cyclic amide of formula 5 in the presence of copper(I) iodide having a diamine ligand, such as trans-N,N'-dimethylcyclohexane-1,2-diamine or tetramethylethylenediamine (TMEDA), in a suitable solvent and potassium phosphate (K3PO4). The solvent can be, for example, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, or dioxane, which may optionally contain water as a cosolvent. A similar copper-mediated coupling can also be carried out under Chan-Lam conditions in dichloromethane, in the presence of copper(II) acetate (Cu(II)AC2) and pyridine, where the boronic acid of formula 4c (i.e., the compound of formula 4 where X is B(OH)2) is coupled with the compound of formula 5. Alternatively, this cross-coupling can be carried out using the compounds of formulas 4c and 5 under a well-documented Buchwald-Hartwig amination protocol, which includes palladium-mediated reaction with a suitable phosphine ligand, in a suitable solvent such as tetrahydrofuran, toluene, or dichloromethane, either as part of the pre-catalyst or as an additive. In some cases, an auxiliary base, i.e., sodium tert-butoxide or cesium carbonate, is used in the reaction. Examples of suitable palladium catalysts for this conversion include, but are not limited to, tetrakis(triphenylphosphine)palladium(0)[Pd(PPh3)4], bis(triphenylphosphine)palladium chloride[PdCl2(PPh3)2], palladium(II) chloride-tris(2-methylphenyl)phosphine[PdCl2[P(o-Tol)3]2], or [1,1'bis(diphenylphosphino)ferrocene]dichloropalladium(II)[Pd(dppf)Cl2].Finally, this cross-coupling can also be achieved by palladium acetate [Pd(OAc)2] or tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)], which can be optionally used in combination with a suitable phosphine ligand, along with a base such as sodium tert-butoxide in toluene or cesium carbonate in N,N-dimethylformamide. [ka]

[0235] As shown in Scheme 4, the nitrobenzene of formula 4 can be prepared by nitrating the substituted benzene of formula 6 in a mixture of nitric acid and sulfuric acid at a temperature ranging from 0°C to ambient temperature. Other sources of nitronium ions for this nitration include nitronium tetrafluoroborate, acetyl nitrate, and guanidinium nitrate, used in a suitable solvent such as tetramethylene sulfone. The substituted benzene of formula 6 may be commercially available or readily prepared by methods established in the literature. It is recognized that nitration of some of the substituted benzenes of formula 6 may yield a mixture of positional isomers of nitrobenzene that requires separation by chromatography or fractional crystallization techniques. [ka]

[0236] Alternatively, nitrobenzene of formula 4a (i.e., the compound of formula 4 in which X is bromine) or nitrobenzene of formula 4b (i.e., the compound of formula 4 in which X is iodine) can be prepared by halogenating the substituted nitrobenzene of formula 7 in a suitable solvent such as acetic acid, dichloromethane, carbon tetrachloride, chloroform, acetonitrile, or N,N-dimethylformamide using a suitable halogenating reagent such as bromine, iodine, N-bromosuccinimide, or N-iodosuccinimide, according to the established method shown in Scheme 5. Iodobenzene of formula 4b can also be prepared from the benzene of formula 7 by treating it with 2,2,6,6-tetramethylpiperidyl zinc chloride-LiCl (TMPZnCl·LiCl) in tetrahydrofuran or dioxane, followed by the addition of a mixture of iodine and nitric acid and sulfuric acid at a temperature ranging from 0°C to ambient temperature. Bromobenzene and iodobenzene of formulas 4a and 4b can be lithified in tetrahydrofuran or dioxane at temperatures typically in the range of -78°C to 0°C using an alkyllithium reagent, preferably n-butyllithium, followed by the addition of trimethylboroxine and subsequent acid hydrolysis to obtain the corresponding arylboronic acid of formula 4c (i.e., the compound of formula 4 where X is B(OH)2). The conversion of aryl halides to arylboronic acids is a well-established synthetic transformation in the organic chemistry literature. [ka]

[0237] As shown in Scheme 6, the cyclic amide of formula 5a can be prepared from the hydroxy-substituted N-protected cyclic amide of formula 8, where PG represents a protecting group such as Cbz (benzyloxycarbonyl) or BOC (tert-butyloxycarbonyl) group. The compound of formula 9 is obtained by alkylating the compound of formula 8 with a suitable alkylating agent in a solvent such as tetrahydrofuran or dioxane, in the presence of a base such as sodium hydride, potassium tert-butoxide, or sodium methoxide, at a temperature generally ranging from 0°C to reflux. The compound of formula 5a is then obtained by removing the N-protecting group CBZ by catalytic hydrogenation (usually in hydrogen in the presence of palladium carbon in methanol or ethanol). The compound of formula 5a can be obtained by removing the N-protecting group BOC with trifluoroacetic acid. The intermediate cyclic amide of formula 9 can also be prepared from the cyclic amide of formula 10 (where LG represents a suitable leaving group such as a halogen (i.e., chlorine, bromine, or iodine) or mesylate). In the presence of a base such as sodium hydride, potassium tert-butoxide, or sodium methoxide, and in a solvent such as tetrahydrofuran or dioxane, the compound of formula 10 is dissolved in a solvent such as tetrahydrofuran or dioxane at a temperature usually ranging from 0°C to the reflux temperature of the solvent. 10 When reacted with an OH nucleophile, the compound shown in formula 9 is obtained. [ka]

[0238] Compound of formula 3a (i.e., G is OR) 10Compound 3 of formula (which is ) can also be obtained by the synthetic route shown in Scheme 7. By cross-coupling a meta-bromo or meta-iodosubstituted nitrobenzene of formula 4a or 4b (i.e., a compound of formula 4 where X is bromine or iodine) with a hydroxysubstituted cyclic amide of formula 11, using the same method as described for the cross-coupling in Scheme 3, a compound of formula 12 having a free hydroxyl group can be obtained. By alkylating 12 with a suitable alkylating agent in the presence of a base such as sodium hydride, potassium tert-butoxide, or sodium methoxide in a solvent such as tetrahydrofuran or dioxane, generally at a temperature ranging from 0°C to the reflux temperature of the solvent, a compound of formula 3a can be obtained. Alternatively, the compound of formula 3a can sometimes be prepared by the method outlined in Scheme 8. By cross-coupling an unprotected cyclic amide of formula 13 with a substituted nitrobenzene of formula 4 under the same cross-coupling conditions as described in Scheme 3, a compound of formula 14 can be obtained. The unprotected cyclic amide of formula 13 comprises both a suitable leaving group LG (where LG is bromine, chlorine, or iodine) and a free amide NH group. In a suitable solvent such as tetrahydrofuran, dioxane, methanol, ethanol, dimethyl sulfoxide, or N,N-dimethylformamide, the leaving group LG on 14 is removed by sodium alkoxide or potassium alkoxide (NaOR 10 or KOR 10 Substitution with ) yields the compound of formula 3a. [ka]

[0239] Alternatively, the compound of formula 3b (i.e., G is SR) 10 The compound of formula 3 can be prepared as shown in scheme 9. The leaving group LG on the compound of formula 14 is removed by a sodium or potassium thiol reagent (NaSR) in a suitable solvent such as tetrahydrofuran, dioxane, acetonitrile, or N,N-dimethylformamide at a temperature ranging from 0°C to the reflux temperature of the solvent. 10 Or KSR 10By substitution using ), the compound of formula 3b can be obtained. When sulfur is oxidized with a suitable oxidizing agent such as metachloroperoxybenzoic acid (MCPBA), sodium periodate, or oxone, the corresponding sulfoxide (SOR) is obtained. 10 ) and sulfone (SO2R 10 ) can be obtained. [ka]

[0240] Scheme 10 outlines a method for producing the compound of formula 5b (i.e., the compound of formula 5 where X is O) or the compound of formula 5c (i.e., the compound of formula 5 where X is S). Based on known methods (see Eur.J.Org.Chem.2020,3013-3018), the cyclic amide protected with BOC(tert-butyloxycarbonyl) of formula 15 is heated with t-butoxybis-(dimethylamino)methane in toluene or xylene at reflux temperature to obtain the corresponding enamine adduct 16. Compound 16 can be reacted with sodium azide in aqueous acetonitrile in the presence of chlorosulfonylbenzoic acid and potassium carbonate to produce a diazo compound 17. Compound 17 can be reacted with alcohol (R) catalyzed with rhodium. 10 OH)OH bond or thiol (R 10 The SH bond undergoes a carbenoid insertion reaction, resulting in the OR of formula 18b where X is O or formula 18c where X is S. 10 or SR 10 Substituted BOC-protected cyclic amides can be produced. Generally, when the BOC protecting group is removed in trifluoroacetic acid under acidic conditions, a free cyclic amide of formula 5b (where X is O) or formula 5c (where X is S) is obtained. This is R 10 The portion may be branched, cyclic, or bulky substituents OR 10 Base and SR 10 This is a particularly useful method for introducing a base. [ka]

[0241] R 4 C(=O)R 14 , C(=S)R 14 CO2R 14 , C(=O)SR 14 S(O)2R 14 CONR 13 R 14 , S(O)2NR 13 R 14 CH2OC(=O)NR 13 R 14 CH2OC(=O)OR 14 , or CH2O(C=O)R 14 The compound of formula 1 is used in the presence of a base such as triethylamine, pyridine, diisopropylethylamine (Hünig base), or potassium carbonate, in a solvent including but not limited to tetrahydrofuran, dioxane, dichloromethane, acetonitrile, or N,N-dimethylformamide, R 4 The sulfonanilide of formula 1, in which hydrogen is appropriately substituted with acyl halogens, thioacyl halogens, carbamoyl halogens, sulfonyl halogens, sulfamoyl halogens, and acyloxymethyl halogens (i.e., ClCH2O(C=O)R 14 ) or can be produced by reacting it with a similar halide or other capping agent (Scheme 11). [ka]

[0242] Compound of formula 1c (i.e., R 4 H is G and R 5 Together they become N-OR 15 It forms R 15 Compounds of formula 1 (where R is not H) are used in solvents such as tetrahydrofuran in the presence of a base such as potassium tert-butoxide or sodium hydride, at temperatures generally ranging from 0°C to the reflux temperature of the solvent, and are used to form compounds of formula 1d (i.e., R 4 H is G and R 5It can be prepared by treating the compound of formula 1 (in which the two groups together form an N-OH group) with a suitable alkylating agent. [ka]

[0243] Compound of formula 1d (i.e., R 4 H is G and R 5 Compounds of formula 1 (in which the ions combine to form an N-OH group) can be prepared by treating the compound of formula 19 with a strong base, such as sodium bis(trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, or lithium diisopropylamide, but not limited to these, and an alkyl nitrite, such as isopentyl nitrite or tert-butyl nitrite, but not limited to these, as a nitrosylation agent. The reaction is typically carried out in a solvent such as tetrahydrofuran at a temperature in the range of approximately -78°C to 50°C. Representative examples can be found in Chem. Pharm. Bull. 1986, vol. 34, pp. 2732-2742 and Org. Lett. 2021, vol. 23, pp. 5394-5399. Compounds of formula 19 can be prepared using the above description. [ka]

[0244] Those skilled in the art recognize that different compounds of formula 1 can be provided by converting various functional groups to other functional groups. For a valuable resource that provides a simple and direct explanation of the interconversion of functional groups, see Larock, RC, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed. Wiley-VCH, New York, 1999. For example, an intermediate for preparing a compound of formula 1 may contain an aromatic nitro group, which can be reduced to an amino group and then converted to various halides by reactions well known in the art, such as the Sandmeyer reaction, to provide a compound of formula 1. These reactions can often be carried out in an alternating order.

[0245] It is recognized that some of the reagents and reaction conditions described above for preparing the compounds of Formula 1 may not be compatible with certain functional groups present in the intermediates. In these examples, incorporating a series of protection / deprotection or functional group interconversions into the synthesis helps to obtain the desired product. The use and selection of protecting groups is obvious to those skilled in the art of chemical synthesis (see, e.g., Greene, TW; Wuts, PGMP Rotective Groups in Organic Synthesis, 2nd Ed.; Wiley: New York, 1991). Those skilled in the art will recognize that, in some cases, after introducing a given reagent, as shown in any individual scheme, it may be necessary to perform additional, standard synthetic steps not described in detail to complete the synthesis of the compounds of Formula 1. Those skilled in the art will also recognize that it may be necessary to perform combinations of steps shown in the above schemes in an order other than that indicated by the specific order presented for preparing the compounds of Formula 1.

[0246] Those skilled in the art will also recognize that the compounds of Formula 1 and the intermediates described herein can be subjected to a variety of electrophilic, nucleophilic, radical organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0247] Those skilled in the art, using the preceding description, will likely be able to utilize the present invention to its fullest extent without any extra effort. The following non-limiting examples are illustrative of the present invention. The steps in the following examples illustrate the procedure of each step in the overall synthetic transformation, and the starting materials for each step may not necessarily have been prepared by other examples or specific preparative operations described in the steps. Percentages are by weight unless otherwise indicated for chromatographic solvent mixtures or other materials. Unless otherwise indicated, parts and percentages of chromatographic solvent mixtures are by weight. 1 ¹HNMR spectra are reported in ppm low field from tetramethylsilane, where 's' means singlet, 'd' means doublet, 't' means triplet, 'q' means quartet, 'm' means multiplet, 'dd' means doublet-doublet, 'ddd' means doublet-doublet-doublet, 'dt' means doublet-triplet, and 'br s' means broad singlet. Mass spectra (MS) are reported as the molecular weight of the parent ion with the highest isotopic abundance, formed by the addition of H+ (molecular weight 1) to the molecule (M+1), or formed by the loss of H+ (molecular weight 1) from the molecule (M-1), observed using liquid chromatography connected to a mass spectrometer (LCMS) using either atmospheric pressure chemical ionization (AP+), where 'amu' represents unified atomic mass units.

[0248] The following non-limiting examples are intended to illustrate the processes of the present invention for preparing the compounds of Formula 1 and the corresponding intermediates. All NMR spectra are reported in CDCl3 from tetramethylsilane at a low field of 500 MHz unless otherwise indicated.

[0249] Synthesis Example 1 Preparation of [[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (compound 5) Step A: Preparation of tert-butyl 3-(cyclopentoxy)-2-oxo-pyrrolidine-1-carboxylate To a solution of tert-butyl 3-diazo-2-oxopyrrolidine-1-carboxylate (300 mg, 1.42 mmol) and cyclopentanol (0.26 mL, 2.84 mmol) in dichloromethane (5 mL), rhodium(II) acetate (19 mg, 3 mol%) was added. The mixture was stirred at room temperature for 2 hours and then concentrated under reduced pressure. The residue was purified by column chromatography (gradient of 0-60% ethyl acetate in hexane on silica) to obtain the target product (342 mg) as a clear oil. 1 H NMR(CDCl3)δ 1.53(s,9H),1.55-1.62(m,4H),1.71-1.82(m,4H),1.86-1.98(m,1H)2.23-2.29(m,1H),3.52(ddd,J=10. 92,8.08,7.17Hz,1H),3.79(ddd,J=10.88,8.51,3.78Hz,1H),4.05(t,J=7.88Hz,1H),4.36-4.41(m,1H).

[0250] Step B: Preparation of 3-(cyclopentoxy)pyrrolidine-2-one To a solution of tert-butyl 3-(cyclopentoxy)-2-oxo-pyrrolidine-1-carboxylate (i.e., the product of step A) (342 mg, 1.27 mmol) in dichloromethane (5 mL), trifluoroacetic acid (0.29 mL, 3.81 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours, then quenched with NaHCO3 (aqueous solution) and extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure to obtain 3-(cyclopentoxy)pyrrolidine-2-one (191 mg) as a clear oil. This was used without further purification. 1H NMR(CDCl3)δ 1.48-1.62(m,4H),1.64-1.86(m,4H),2.01-2.10(m,1H),2.37-2.46(m,1H),3.27(dt,J=9.50, 7.23Hz,1H),3.41(td,J=8.99,3.63Hz,1H),4.02(t,J=7.49Hz,1H),4.30-4.38(m,1H),6.03(br s,1H).

[0251] Step C: Preparation of 3-(cyclopentoxy)-1-(2,4-dimethyl-5-nitrophenyl)pyrrolidine-2-one To a 25 mL scintillation vial with a septum, copper(I) iodide (45 mg, 25 mol%), potassium carbonate (390 mg, 2.82 mmol), 3-(cyclopentoxy)pyrrolidine-2-one (i.e., the product of step B) (191 mg, 1.13 mmol), and 1-bromo-2,4-dimethyl-5-nitrobenzene (216 mg, 0.94 mmol) were added. After purging the reaction vial with nitrogen gas, dioxane (5 mL) and trans-N,N'-dimethylcyclohexane-1,2-diamine (0.074 mL, 50 mol%) were added to the reaction vial via syringe. The reaction mixture was stirred overnight at 100°C under nitrogen, then diluted with ethyl acetate and filtered through a Celite® diatomaceous earth filter aid pad. The resulting filtrate was dried over magnesium sulfate and concentrated under reduced pressure to obtain the residue. The residue was purified by column chromatography (gradient of 0-60% ethyl acetate in hexane on silica) to obtain the target product (279 mg) as a clear oil. 1H NMR(CDCl3)δ:1.49-1.61(m,3H),1.67-1.86(m,5H),2.17(ddt,J=13.00,8.04,6.42,6.42Hz,1H),2.27(s,3H),2.46-2.54(m,1H),2.60(s,3H) ),3.64(ddd,J=9.65,7.29,6.38Hz,1H),3.73(ddd,J=9.62,8.04,4.57Hz,1H),4.18-4.21(m,1H),4.38-4.49(m,1H),7.24(s,1H),7.86(s,1H)

[0252] Step D: Preparation of 1-(5-amino-2,4-dimethylphenyl)-3-(cyclopentoxy)pyrrolidine-2-one To a stirred solution of 3-(cyclopentoxy)-1-(2,4-dimethyl-5-nitro-phenyl)pyrrolidine-2-one (i.e., the product of step C) (278 mg, 0.87 mmol) in ethyl acetate (4 mL), a solution of ammonium chloride (93 mg, 1.75 mmol) in water (1 mL) was added. Then, iron powder (146 mg, 2.62 mmol) was added, and the mixture was stirred overnight at 80°C under nitrogen. The mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a Celite® diatomaceous earth filter aid pad. The filtrate was concentrated under reduced pressure to obtain the title compound (275 mg). This was used without further purification. 1 H NMR(CDCl3)δ 1.42-1.62(m,3H),1.66-1.86(m,5H),2.04-2.25(m,7H),2.38-2.51(m,1H),3.53(ddd,J=9.77,7.41,6.46H z,1H),3.65(ddd,J=9.81,8.16,4.41Hz,1H),4.16-4.18(m,1H),4.37-4.53(m,1H),6.48(s,1H)6.92(s,1H).

[0253] Step E: Preparation of N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide To a stirred solution of 1-(5-amino-2,4-dimethylphenyl)-3-(cyclopentoxy)pyrrolidine-2-one (i.e., the product of step D) (275 mg, 0.95 mmol) in dichloromethane (4.8 mL), triethylamine (0.279 mL, 2.00 mmol) was added. The mixture was cooled to -78°C, and then trifluoromethanesulfonic anhydride (0.34 mL, 2.00 mmol) was added dropwise. The reaction mixture was then stirred at room temperature for 1 hour, followed by quenching with aqueous NaHCO3 and extraction with dichloromethane. The combined organic layers were dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography (gradient of 0-60% ethyl acetate in hexane on silica) to obtain the title compound (380 mg). 1 H NMR(CDCl3)δ 1.50-1.61(m,3H),1.68-1.89(m,5H),2.16(ddt,J=13.10,8.18,6.54,6.54Hz,1H),2.25(s,3H),2.39(s,3H),2.45-2.55(m,1H) ,3.56-3.63(m,1H),3.66-3.73(m,1H),4.20(dd,J=7.41,6.62Hz,1H),4.43(tt,J=5.87,3.59Hz,1H),7.08(s,1H),7.26(s,1H).

[0254] Step F: Preparation of N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide To a stirred solution of N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (i.e., the product of step E) (380 mg, 0.69 mmol) in dioxane (6.8 mL), 1 N aqueous sodium hydroxide solution (0.72 mL, 0.72 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 3 hours, then neutralized with 1 N aqueous hydrogen chloride solution and extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography (on silica, gradient of 0-50% ethyl acetate in hexane) to obtain the title compound (160 mg) as a white solid. 1 H NMR(CDCl3)δ 1.50-1.60(m,2H),1.65-1.86(m,6H),2.12-2.19(m,7H),2.43-2.52(m,1H),3.54(ddd,J=10.01,7.49,6.46Hz,1H),3.6 6(ddd,J=10.01,8.28,4.41Hz,1H),4.24(dd,J=7.72,6.31Hz,1H),4.46-4.53(m,1H),6.87(s,1H),7.03(s,1H),8.65(br s,1H).

[0255] Step G: Preparation of [[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate To a stirred solution of N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (i.e., the product of step F (70 mg, 0.17 mmol)) in dichloromethane (5 mL), triethylamine (0.058 mL, 0.42 mmol) and chloromethyl 2,2-dimethylpropanoate (0.048 mL, 0.33 mmol) were added. The reaction mixture was stirred overnight at 45-50°C and then concentrated under reduced pressure. The residue was purified by column chromatography (on silica, gradient of 0-100% ethyl acetate in hexane) to obtain the title compound (75 mg) as a clear oil. 1 H NMR(CDCl3)δ 1.20(d,J=3.63Hz,9H),1.50-1.60(m,2H),1.66-1.87(m,6H),2.10 -2.18(m,1H),2.21(d,J=9.62Hz,3H),2.38(s,3H),2.41-2.52(m,1H),3.52-3.57(m,1H),3.64-3.75(m,1H),4.13-4. 18(m,1H),4.41-4.45(m,1H),5.42(t,J=10.64Hz,1H),5.70(t,J=11.59Hz,1H),7.05(d,J=17.50Hz,1H),7.22(s,1H).

[0256] Synthesis Example 2 Preparation of N-[2,4-dimethyl-5-[2-oxo-3-(2-propyne-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-trifluoromethanesulfonamide (compound 1) Step A: Preparation of 1-(2,4-dimethyl-5-nitrophenyl)-3-hydroxypyrrolidine-2-one To a solution of 1-bromo-2,4-dimethyl-5-nitrobenzene (2.50 g, 10.86 mmol) in 1,4-dioxane (20 mL), 3-hydroxypyrrolidine-2-one (2.74 g, 27.17 mmol) was added, and K2CO3 (4.50 g, 32.60 mmol), copper(I) iodide (2.06 g, 10.86 mmol), and N,N'-dimethylethylenediamine (DMEDA) (2.3 mL, 21.73 mmol) were added at room temperature. The reaction mixture was degassed under N2 for 10 minutes and then stirred at 110°C for 16 hours. The reaction mixture was filtered through Celite® diatomaceous earth filter aid and washed with ethyl acetate (50 mL). The filtrate was removed by reduced pressure distillation, and the target product (2.2 g) was obtained as an off-white solid by trituration with n-pentane (25 mL) and diethyl ether (5 mL). 1 H NMR(CDCl3)δ 7.87(s,1H),7.26(s,1H),5.54-4.99(t,1H),3.76-3.65(m,2H),2.94(b r,1H),2.66-2.63(m,1H),2.60(s,3H),2.27(s,3H),2.26-2.20(m,1H).

[0257] Step B: Preparation of 1-(2,4-dimethyl-5-nitrophenyl)-3-prop-2-inoxypyrrolidine-2-one To a solution of 1-(2,4-dimethyl-5-nitrophenyl)-3-hydroxy-pyrrolidine-2-one (i.e., the product of step A) (1.5 g, 6 mmol) in THF (30 mL), NaH (0.432 g, 18 mmol, 60%) and propargyl bromide (1.36 mL, 18 mmol) were added at 0°C. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched with saturated aqueous NH4Cl (10 mL) and extracted with ethyl acetate (25 mL x 2). The combined organic layer was dried over anhydrous Na2SO4. The crude product was obtained by concentrating the solvent under reduced pressure. The crude product was packed into a silica gel column. The target product (500 mg) was obtained as a pale yellow solid by eluting the column with 30% ethyl acetate / petroleum ether. LCMS(M+1) = 289.

[0258] Step C: Preparation of 1-(5-amino-2,4-dimethylphenyl)-3-(2-propyne-1-yloxy)-2-pyrrolidinone To a solution of 1-(2,4-dimethyl-5-nitrophenyl)-3-prop-2-inoxypyrrolidine-2-one (i.e., the product of step B) (0.400 g, 1.38 mmol) in ethanol (16 mL) and water (4 mL), iron (powder, 0.387 g, 6.94 mmol) and NH4Cl (0.074 g, 1.38 mmol) were added. The reaction mixture was heated to a reflux temperature of 80 °C for 3 hours. After the reaction was complete, the reaction mixture was filtered through Celite® diatomaceous earth filter aid and washed with ethyl acetate (25 mL). The filtrate was removed by vacuum distillation to obtain the crude product (0.240 g) as an off-white solid. This was used in the next step. LCMS(M+1) = 259.

[0259] Step D: Preparation of N-[2,4-dimethyl-5-[2-oxo-3-(2-propyne-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-trifluoromethanesulfonamide To a solution of 1-(5-amino-2,4-dimethylphenyl)-3-(2-propyne-1-yloxy)-2-pyrrolidinone (i.e., the product of step C) (0.210 g, 0.81 mmol) in dichloromethane (10 mL), triethylamine (0.2 mL, 1.62 mmol) and trifluoromethanesulfonic anhydride (Tf2O) (0.08 mL, 0.48 mmol) were added at -78 °C. The reaction mixture was stirred at room temperature for 1 hour. After the reaction was complete, the reaction mixture was quenched with water (20 mL) and extracted with dichloromethane (20 mL × 2). The organic layer was separated, washed with brine (10 mL), and concentrated under reduced pressure to obtain the crude compound. This was loaded onto a silica gel column. The column was eluted with 30% ethyl acetate / petroleum ether to obtain the target product (80 mg) as an off-white solid. 11H NMR (CDCl3) δ 7.99 (br, 1H), 7.06 (s, 1H), 6.97 (s, 1H), 4.65 - 4.53 (m, 2H), 4.46 - 4.42 (t, 1H), 3.70 - 3.57 (m, 2H), 2.59 - 2.56 (m, 1H), 2.50 - 2.49 (t, 1H), 2.26 - 2.24 (m, 1H), 2.21 (s, 3H), 2.16 (s, 3H).

[0260] Synthesis Example 3 Preparation of N-[5-[3-(Cyclopropoxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (also known as N-[5-[3-([Cyclopropoxy)-2-oxo-pyrrolidin-1-yl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (Compound 3) Step A: Preparation of tert-butyl 3-(cyclopropoxy)-2-oxo-pyrrolidine-1-carboxylate To a solution of tert-butyl 3-diazo-2-oxopyrrolidine-1-carboxylate (2 g, 9.47 mmol) and cyclopropanol (0.82 g, 14.21 mmol) in dichloromethane (20 mL) was added rhodium(II) acetate (41 mg, 0.01 mmol). The mixture was stirred at room temperature for 1 hour. Analysis by thin layer chromatography (50% ethyl acetate / petroleum ether) indicated completion of the reaction. The reaction mixture was filtered through Celite® diatomaceous earth filter aid. The filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was loaded onto a silica gel column. Elution of the column with 30% ethyl acetate / petroleum ether gave the pure desired product (0.680 g) as an off-white solid. 1 1H NMR (CDCl3) δ 4.17 - 4.13 (t, 1H), 3.82 - 3.77 (m, 2H), 3.57 - 3.52 (m, 1H), 2.28 - 2.27 (m, 1H), 1.96 - 1.91 (m, 1H), 1.53 (s, 9H), 0.72 - 0.49 (m, 4H).

[0261] Step B: Preparation of 3-(cyclopropoxy)pyrrolidin-2-one Trifluoroacetic acid (0.89 g, 7.84 mmol) was added dropwise to a solution of tert-butyl 3-(cyclopropoxy)-2-oxo-pyrrolidine-1-carboxylate (i.e., the product of step A) (0.680 g, 2.61 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 4 hours. Analysis by thin-layer chromatography (45% ethyl acetate / petroleum ether) indicated completion of the reaction. The reaction mixture was removed by distillation under reduced pressure to obtain the crude product. The crude product was co-distilled with CHCl3 (10 mL × 2) to obtain 3-(cyclopropoxy)pyrrolidine-2-one (0.6 g) as a clear oily liquid. 1 H NMR(CDCl3)δ 7.69(br,1H),4.3-4.26(m,1H),3.71-3.68(m,1H),3.56-3.50(m,1H),3. 43-3.37(m,1H),2.52-2.44(m,1H),2.16-2.07(m,1H),0.74-0.54(m,4H).

[0262] Step C: Preparation of 3-(cyclopropoxy)-1-(2,4-dimethyl-5-nitrophenyl)pyrrolidine-2-one To a solution of 3-(cyclopropoxy)pyrrolidine-2-one (i.e., the product of step B) (0.6 g, 4.25 mmol) in dioxane in a sealed container, 1-bromo-2,4-dimethyl-5-nitrobenzene (2.12 g, 8.5 mmol), K2CO3 (2.5 g, 17.02 mmol), and N,N'-dimethylethylenediamine (DMEDA) (0.81 g, 8.5 mmol) were added. The reaction was degassed with N2 gas for 5 minutes. Copper(I) iodide (0.875 g, 4.2 mmol) was added to the reaction mixture, and the reaction mixture was heated to reflux temperature at 110°C for 12 hours. The reaction mixture was diluted with ethyl acetate and filtered through a Celite® diatomaceous earth filter aid pad. The resulting filtrate was concentrated under reduced pressure to obtain the residue. The residue was purified by column chromatography (30% ethyl acetate in petroleum ether on silica) to obtain the target product (0.650 g) as a white solid. 1H NMR(CDCl3)δ 7.86(s,1H),7.26(s,1H),4.32-4.28(t,1H),3.82-3.79(m,1H),3.75-3.70(m,2H), 2.60(s,3H),2.28(s,3H),2.58-2.53(m,1H),2.23-2.18(m,1H),0.79-0.54(m,4H).

[0263] Step D: Preparation of 1-(5-amino-2,4-dimethylphenyl)-3-(cyclopropyloxy)-2-pyrrolidinone To a solution of 3-(cyclopropoxy)-1-(2,4-dimethyl-5-nitro-phenyl)pyrrolidine-2-one (i.e., the product of step C) (0.610 g, 2.10 mmol) in ethanol (5 mL) and water (5 mL), iron (powder, 0.587 g, 10.55 mmol) and NH4Cl (0.336 g, 6.310 mmol) were added. The reaction mixture was heated at 80 °C for 2 hours. After the reaction was complete, the reaction mixture was filtered through Celite® diatomaceous earth filter aid and washed with ethyl acetate (25 mL). The filtrate was removed by reduced pressure distillation to obtain the crude product. This was loaded onto a silica gel column. The column was eluted with 40% ethyl acetate / petroleum ether to obtain the target product (0.49 g) as an off-white solid. 1 H NMR(CDCl3)δ 6.93(s,1H),6.46(s,1H),4.29-4.26(t,1H),3.83-3.80(m,1H),3.66-3.55(m,2H), 2.49-2.44(m,1H),2.18-2.12(m,1H),2.11(s,3H),2.08(s,3H),0.76-0.52(m,4H).

[0264] Step E: Preparation of N-[5-[3-(cyclopropoxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (also known as N-[5-[3-(cyclopropoxy)-2-oxo-pyrrolidin-1-yl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide) To a solution of 1-(5-amino-2,4-dimethylphenyl)-3-(cyclopropyloxy)-2-pyrrolizinone (i.e., the product of step D) (350 mg, 1.34 mmol) in dichloromethane (10 mL), triethylamine (0.37 mL, 2.26 mmol) and Tf2O (0.34 mL, 2.01 mmol) were added at -20°C. The reaction mixture was stirred at room temperature for 3 hours. Analysis by thin-layer chromatography (50% ethyl acetate / petroleum ether) indicated completion of the reaction. The reaction mixture was quenched with water (50 mL) and extracted with dichloromethane (50 mL × 2). The organic layer was separated, washed with brine (25 mL), and dried over Na2SO4. The solvent was removed by distillation and the mixture was loaded onto a silica gel column. The target product (140 mg) was obtained as an off-white solid by eluting the column with 20% ethyl acetate / petroleum ether. 1 H NMR(CDCl3)δ 8.12(s,1H),7.06(s,1H),6.95(s,1H),4.35-4.31(t,1H),3.89-3.84(m,1H),3.69-3.55(m,2H), 2.55-2.48(m,1H),2.22(s,3H),2.17(s,3H),2.17(m,1H),0.81-0.76(m,1H),0.68-0.62(m,3H).

[0265] Synthesis Example 4 Preparation of 1,1,1-trifluoro-N-[5-[3-(hydroxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]methanesulfonamide (compound 10) Step A: Preparation of 1-(2,4-dimethyl-5-nitrophenyl)pyrrolidine-2-one To a stirred solution of 1-bromo-2,4-dimethyl-5-nitrobenzene (5 g, 21.7 mmol) in 1,4-dioxane (50 mL), pyrrolidine-2-one (4.6 g, 54.1 mmol), potassium carbonate (8.9 g, 64.4 mmol), copper(I) iodide (3.9 g, 20.5 mmol), and N,N'-dimethylethylenediamine (3.82 g, 43.3 mmol) were added. The mixture was sparged with nitrogen gas for 10 minutes, then stirred at 130°C for 16 hours. The mixture was filtered through a Celite pad and rinsed with ethyl acetate (50 mL). The filtrate was concentrated under reduced pressure and triturated with n-pentane (25 mL) and diethyl ether (5 mL) to obtain the title compound as an off-white solid (5 g). 1 H NMR(CDCl3)δ 7.87(s,1H),7.24(s,1H),3.78-3.75(m,2H),2.61-2.57(m,5H),2.30-2.24(m,5H).

[0266] Step B: Preparation of 1-(5-amino-2,4-dimethylphenyl)pyrrolidine-2-one To a stirred solution of 1-(2,4-dimethyl-5-nitrophenyl)pyrrolidine-2-one (i.e., the product of step A) (5 g, 21.3 mmol) in ethanol (40 mL) and water (12 mL), iron powder (6 g, 107 mmol) was added, followed by ammonium chloride (1.13 g, 21.1 mmol). The mixture was stirred at 80°C for 3 hours, then filtered through a Celite® diatomaceous earth filter aid pad and rinsed with ethyl acetate (25 mL). The filtrate was concentrated under reduced pressure to obtain the title compound as an off-white solid (4 g). This was used without further purification. 1 H NMR(CDCl3)δ 6.92(s,1H),6.46(s,1H),3.67-3.64(m,2H),3.53(br s,2H),2.55-2.52(m,2H),2.21-2.15(m,2H),2.11(s,3H),2.08(s,3H).

[0267] Step C: Preparation of N-[2,4-dimethyl-5-(2-oxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide To a stirred solution of 1-(5-amino-2,4-dimethylphenyl)pyrrolidin-2-one (i.e., the product of Step B) (4 g, 19.6 mmol) in dichloromethane (40 mL) at -78 °C was added triethylamine (5.9 mL, 42 mmol) and trifluoromethanesulfonic anhydride (3.2 mL, 19 mmol). After 2 h, water (20 ml) was added and the mixture was extracted with ethyl acetate (200 mL×2). The combined organic layers were washed with brine (50 mL) and concentrated under reduced pressure. Column chromatography on silica gel afforded the title compound as an off-white solid (3 g). 1 H NMR (CDCl3) δ 7.05 (s, 1H), 6.95 (s, 1H), 3.70 - 3.67 (m, 2H), 2.63 - 2.60 (m, 2H), 2.27 - 2.21 (m, 2H), 2.20 (s, 3H), 2.17 (s, 3H).

[0268] Step D: Preparation of 1,1,1-trifluoro-N-[5-[3-(hydroxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]methanesulfonamide To a stirred solution of N-[2,4-dimethyl-5-(ioxopyrrolidin-1-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (i.e., the product of Step C) (3 g, 8.9 mmol) in anhydrous tetrahydrofuran (30 mL) at 0 °C was added sodium bis(trimethylsilyl)amide (30 mL, 30 mmol, 1 M in tetrahydrofuran). The mixture was stirred at 0 °C for 30 min, then isopentyl nitrite (2.2 g, 18.8 mmol) was added and the mixture was stirred at 0 °C for 2 h. The mixture was quenched with 1 N hydrochloric acid (30 mL) and extracted with ethyl acetate (100 mL×2). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. Trituration with 10% diethyl ether / pentane afforded the title compound as an off-white solid (1.6 g). 1H NMR(DMSO-d6)δ 11.95(s,1H),11.52(br s,1H),7.24(br s,1H),7.16(s,1H),3.72(m,2H),2.88(m,2H),2.27(s,3H),2.10(s,3H).

[0269] Synthesis Example 5 Preparation of N-[5-[3-(ethoxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (compound 12) To a stirred solution of 1,1,1-trifluoro-N-[5-[3-(hydroxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]methanesulfonamide (i.e., the product of step D in Synthesis Example 4) (0.4 g, 1.09 mmol) in tetrahydrofuran (20 mL), potassium tert-butoxide (3.8 mL, 3.8 mmol, 1 M in tetrahydrofuran) was added at room temperature. The mixture was stirred for 20 minutes, then bromoethane (0.1 mL, 1.3 mmol) was added. After stirring for 16 hours, the mixture was acidified to approximately pH 4 with 1N hydrochloric acid and extracted with ethyl acetate (50 mL x 2). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The title compound was obtained as an off-white solid by column chromatography on silica gel (160 mg). 1 H NMR(DMSO-d6)δ 11.48(br s,1H),7.26(s,1H),7.19(s,1H),4.24(q,2H),3.73(m,2H),2.90(m,2H),2.28(s,3H),2.11(s,3H),1.27(t,3H).

[0270] The compounds listed in Tables 1 to 11 below can be prepared by the procedures described herein and by methods known in the art. In the following tables, the following abbreviations are used: t means tertiary, s means secondary, n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, i-Pr means isopropyl, Bu means butyl, c-Pr means cyclopropyl, c-Bu means cyclobutyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, NHMe means methylamino, -CN means cyano, Py means pyridinyl, -NC2 means nitro, TMS means trimethylsilyl, S(O)Me means methylsulfinyl, and S(O)2Me means methylsulfonyl.

[0271] [Table 1]

[0272] This disclosure also includes Tables 2-25, in which the words in the row of the heading in Table 1 (i.e., "R") are used. 4 The '=H' is replaced with the word in the heading row listed in each table. The remaining variable parts are as defined in Table 1.

[0273] [Table 2]

[0274] [Table 3]

[0275] This disclosure also includes Tables 27-50, in which the words in the row of the heading in Table 26 (i.e., "R") 4The '=H' is replaced with the word in the heading row listed in each table. The remaining variable parts are as defined in Table 26.

[0276] [Table 4]

[0277] [Table 5]

[0278] This disclosure also includes Tables 52-75, in which the words in the row of the heading in Table 51 (i.e., "R") 4 =H") is replaced with the word in the heading row listed in each table, R 10 This is defined in Table 51.

[0279] [Table 6]

[0280] [Table 7]

[0281] This disclosure also includes Tables 77-100, in which the words in the row of the heading in Table 76 (i.e., "R") 4 =H") is replaced with the word in the heading row listed in each table, R 10 This is as defined in Table 76.

[0282] [Table 8]

[0283] [Table 9]

[0284] This disclosure also includes Tables 102-125, in which the words in the row of the heading in Table 101 (i.e., "R") 4 The '=H' is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 101.

[0285] [Table 10]

[0286] [Table 11]

[0287] This disclosure also includes Tables 127-150, in which the words in the row of the heading in Table 126 (i.e., "R") 4 The part "=H") is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 126.

[0288] [Table 12]

[0289] [Table 13]

[0290] This disclosure also includes Tables 152-175, in which the words in the row of the heading of Table 151 (i.e., "R") 4 The part "=H") is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 151.

[0291] [Table 14]

[0292] [Table 15]

[0293] This disclosure also includes Tables 177-200, in which the row of the heading in Table 176 (i.e., "R") 4 The '=H' is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 176.

[0294] [Table 16]

[0295] [Table 17]

[0296] This disclosure also includes Tables 202-225, in which the row of the heading in Table 201 (i.e., "R") 4 The part "=H") is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 201.

[0297] [Table 18]

[0298] [Table 19]

[0299] This disclosure also includes Tables 227-250, in which the row of the heading in Table 226 (i.e., "R") 4 The part "=H") is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 226.

[0300] [Table 20]

[0301] [Table 21]

[0302] This disclosure also includes Tables 252-275, in which the row of the heading in Table 251 (i.e., "R") 4 The part "=H") is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 251.

[0303] [Table 22]

[0304] [Table 23]

[0305] This disclosure also includes Tables 277-300, in which the row of the heading in Table 276 (i.e., "R") 4 The '=H' is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 276.

[0306] [Table 24]

[0307] [Table 25]

[0308] This disclosure also includes Tables 302-325, in which the row of the heading in Table 301 (i.e., "R") 4 The '=H' is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 301.

[0309] [Table 26]

[0310] [Table 27]

[0311] This disclosure also includes Tables 327-350, in which the row of the heading in Table 326 (i.e., "R") 4 The part "=H") is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 326.

[0312] [Table 28]

[0313] [Table 29]

[0314] This disclosure also includes Tables 352-375, in which the row of the heading in Table 351 (i.e., "R") 4 The part "=H") is replaced with the word in the heading row listed in each table, and the remaining variable part is as defined in Table 351.

[0315] [Table 30]

[0316] Formulation / Efficacy The compounds of this disclosure are generally used as herbicidal active ingredients in compositions, i.e., formulations having at least one further component (acting as a carrier) selected from the group consisting of surfactants, solid excipients, and liquid excipients. The components of the formulation or composition are selected in accordance with the physical properties of the active ingredient, the mode of application, and environmental factors such as soil type, moisture, and temperature.

[0317] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, and emulsions (including microemulsions, oil-in-water emulsions, fluid concentrates, and / or suspendemulsions), which may be thickened to form gels. Common types of aqueous liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, fluid concentrates, and suspendemulsions. Common types of non-aqueous liquid compositions are emulsions, microemulsions, dispersible concentrates, and oil dispersions.

[0318] Common types of solid compositions include dust, powders, granules, pellets, prills, pastilles, tablets, and filling films (including seed coatings), which may be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or fluid suspensions are particularly useful for seed treatment. Active ingredients can be (micro)encapsulated or further processed into suspensions or solid formulations; alternatively, the entire active ingredient formulation can be encapsulated (or "overcoated"). By encapsulation, the release of the active ingredient can be controlled or delayed. Emulsified granules combine the advantages of both emulsion formulations and dry granular formulations. High-strength compositions are primarily used as intermediates for further formulations.

[0319] Sprayable formulations are typically diluted in a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily diluted in a spray medium, usually water, but sometimes other suitable mediums, such as aromatic or paraffinic hydrocarbons, or vegetable oils. Spray volumes can range from approximately 1 liter to several thousand liters per hectare, but more typically from approximately 10 liters to several hundred liters per hectare. Sprayable formulations can be tank-mixed with water or other suitable mediums for foliar treatment by aerial or ground spraying, or for application to plant growing media. Liquid and dry formulations can be directly metered and added to drip irrigation systems, or metered and added to furrows during planting.

[0320] The formulation typically contains effective amounts of the active ingredient, diluent, and surfactant within the following general ranges, provided that their total amounts equal 100 percent by weight.

[0321] [Table 31]

[0322] Examples of solid diluents include: clay, such as bentonite, montmorillonite, attapulgite, and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate, and sodium bicarbonate, as well as sodium sulfate. Typical solid diluents are described in the following literature: Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.

[0323] Examples of liquid diluents include: water, N,N-dimethylalkaneamide (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidone (e.g., N-methylpyrrolidinone), alkyl phosphate (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffin (e.g., white mineral oil, normal paraffin, isoparaffin), alkylbenzene, alkylnaphthalene, glycerin, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatic aliphatic compounds, alkylbenzene, alkylnaphthalene, ketones, e.g., cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-phenyl Nononone, acetate esters, such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate, and isobornyl acetate, other esters, such as alkylated lactic acid esters, dibasic esters, alkyl and aryl benzoates, γ-butyrolactone, and alcohols (which may be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol, and benzyl alcohol). Further liquid diluents include: saturated and unsaturated fatty acids (typically C6-C6). 22Glycerol esters of plant seeds and fruits (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., beef tallow, lard, cod liver oil, fish oil), and mixtures thereof. Further liquid diluents include alkylated fatty acids (e.g., methylated, ethylated, and butylated), which can be obtained by hydrolysis of plant and animal glycerol esters and purified by distillation. Typical liquid diluents are described in the following literature: Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[0324] The solid and liquid compositions of the present invention often contain one or more surfactants. When added to a liquid, surfactants (also known as "surface-active agents") generally alter, and in most cases reduce, the surface tension of the liquid. Depending on the properties of the hydrophilic and lipophilic groups in the surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers, or defoamers.

[0325] Surfactants can be classified as nonionic, anionic, or cationic. Examples of nonionic surfactants useful in the compositions of the present invention include, but are not limited to, the following: alcohol alkoxylates, for example, alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear), and prepared from alcohol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof; amine ethoxylates, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, for example, ethoxylated soybean oil, linseed oil, and rapeseed oil; alkylphenol alkoxylates, for example, 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 their terminal blocks being propylene Reverse block polymers prepared from ethylene oxides; ethoxylated fatty acids; ethoxylated aliphatic esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters, e.g., polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters, and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives, e.g., sorbitan esters; polymerizable surfactants, e.g., 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, e.g., sucrose esters, alkyl polyglycosides, and alkyl polysaccharides.

[0326] Useful anionic surfactants include, but are not limited to, the following: alkylaryl sulfonic acids and their salts; carboxylate alcohols or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives, e.g., lignosulfonates; maleic acid or succinic acid, or their anhydrides; olefin sulfonates; phosphate esters, e.g., phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates, and phosphate esters of styrylphenol ethoxylates; protein-based surfactants; sarcosine Derivatives; styrylphenol ether sulfate; 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, e.g., N,N-alkyl taurates; sulfonates of benzene, cumene, toluene, xylene, and dodecylbenzene and tridecylbenzene; sulfonates of condensed naphthalenes; sulfonates of naphthalenes and alkylnaphthalenes; sulfonates of fractionated petroleum; sulfosucciniamidates; and sulfosuccinates and their derivatives, e.g., salts of dialkyl sulfosuccinates.

[0327] Useful cationic surfactants include, but are not limited to, the following: amides and ethoxylated amides; amines, e.g., N-alkylpropanediamine, trippropyltriamine, and dipropylenetetramine, and ethoxylated amines, ethoxylated diamines, and propoxylated amines (prepared from amines with ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); amine salts, e.g., acetate salts of amines and salts of diamines; quaternary ammonium salts, e.g., quaternary salts, ethoxylated quaternary salts, and diquaternary salts; and amine oxides, e.g., alkyldimethylamine oxide and bis-(2-hydroxyethyl)-alkylamine oxide.

[0328] Useful materials for the compositions of the present invention include mixtures of nonionic surfactants and anionic surfactants, or mixtures of nonionic surfactants and cationic surfactants. Nonionic surfactants, anionic surfactants, and cationic surfactants, and their recommended uses, are disclosed in various published references, for example, the following: McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Published Co.; 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.

[0329] The compositions of the present invention may further contain compounding aids and additives known to those skilled in the art as compounding aids (some of which may also function as solid diluents, liquid diluents, or surfactants). Such compounding aids and additives can adjust: pH (buffering agents), foaming during processing (defoaming agents, e.g., polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), microbial growth in containers (antimicrobial agents), product freezing (antifreeze), color (dye / pigment dispersion), wash-off (film-forming agents, or stickers), evaporation (evaporation inhibitors), and other compounding properties. Examples of film-forming agents include: polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of compounding aids and additives are listed in the following publications: McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co., and International Publication No. 03 / 024222.

[0330] The compounds of Formula 1 and other active ingredients are typically incorporated into the compositions of the present invention by dissolving the active ingredients in a solvent or by grinding them in a liquid or dry diluent. Solutions, including emulsions, can be prepared simply by mixing multiple components. When the solvent of a liquid composition intended for use as an emulsion is water-immiscible, an emulsifier is typically added and diluted with water to emulsify the solvent containing the active ingredient. Slurries of active ingredients having particle diameters up to 2,000 μm can be processed in a wet mill using a media mill to obtain particles with an average diameter of less than 3 μm. The aqueous slurry can be made into a final suspension concentrate (see, for example, U.S. Patent No. 3,060,084), or further processed by spray drying to form water-dispersible granules. To obtain a dry formulation, a dry grinding process is usually required, resulting in an average particle diameter in the range of 2 to 10 μm. Fine powders and powders can be prepared by blending and grinding, usually (e.g., using a hammer mill or fluid energy mill). Granules and pellets can be prepared by spraying the active substance onto a pre-formed granular carrier or by agglomeration. See Browning, “Agglomeration”, Chemical Engineering, December 4, 1967, pp. 147-48; Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57; and below; International Publication No. 91 / 13546. Pellets can be prepared according to the description in U.S. Patent No. 4,172,714. Water-dispersible and water-soluble granules can be prepared according to the teachings in U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442, and German Patent No. 3,246,493. Tablets may be prepared in accordance with the teachings of U.S. Patent No. 5,180,587, U.S. Patent No. 5,232,701, and U.S. Patent No. 5,208,030.The film can be prepared in accordance with the teachings of British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

[0331] For further information on formulation technology, please refer to the following literature: T.Swoods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and TR. Roberts, Eds. Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. Furthermore, please refer to the following publications: U.S. Patent No. 3,235,361, Column 6, Row 16 to Column 7, Row 19, and Examples 10-41; U.S. Patent No. 3,309,192, Column 5, Row 43 to Column 7, Row 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; U.S. Patent No. 2,891,855, Column 3, Row 66 to Column 5, Row 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, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

[0332] In the following examples, all percentages are given by weight, and all formulations are prepared by conventional methods. Compound numbers refer to the compounds in Index Table A. Those skilled in the art, using the preceding description, will be able to utilize the present invention to its fullest extent without any extra effort. Therefore, the following examples are merely illustrative and should not be construed as limiting the disclosure in any way. Percentages are given by weight unless otherwise indicated. [Examples]

[0333] Example A high strength concentrate Compound 1 98.5% Silica aerogel 0.5% Synthetic amorphous silica powder 1.0%

[0334] Example B Wettable powder Compound 1 65.0% Dodecylphenol polyethylene glycol ether 2.0% Sodium lignin sulfonate 4.0% Sodium aluminosilicate 6.0% Montmorillonite (calcined product) 23.0%

[0335] Example C granules Compound 1 10.0% Attapulgite granules (low volatility, 0.71 / 0.30 mm; USS No. 25-50 sieve) 90.0%

[0336] Example D Extruded plastic pellets Compound 1 25.0% Anhydrous sodium sulfate 10.0% Crude calcium lignin sulfonate 5.0% Sodium alkylnaphthalene sulfonate 1.0% Calcium / Magnesium Bentonite 59.0%

[0337] Example E emulsifiable concentrate Compound 1 10.0% Polyoxyethylene sorbitol hexaoleate 20.0% C6~C 10 Fatty acid methyl ester 70.0%

[0338] Example F Microemulsion Compound 1 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglycoside 30.0% Glyceryl monooleate 15.0% Water 20.0%

[0339] Example G Suspension concentrate Compound 1 35% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Water 53.7%

[0340] Example H Underwater emulsion Compound 1 10.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Aromatic petroleum-based hydrocarbons 20.0 Water 58.7%

[0341] Example I oil dispersion Compound 1 25% Polyoxyethylene sorbitol hexaoleate 15% Organically modified bentonite clay 2.5% Fatty acid methyl ester 57.5%

[0342] The additional example formulations include Examples A to I described above, in which "Compound 1" is replaced in each of Examples A to I with the respective compound from Index Table A, as shown below.

[0343] [Table 32]

[0344] Test results indicate that the compounds of the present invention are highly active pre-emergence and / or post-emergence herbicides and / or plant growth inhibitors. The compounds of this disclosure generally exhibit the highest activity for post-emergence weed control (i.e., applied after weed seedlings emerge from the soil) and pre-emergence weed control (i.e., applied before weed seedlings emerge from the soil). Many of them are useful for wide-area pre-emergence and / or post-emergence weed control in areas where complete control of all vegetation is desired, such as: around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, airports, riverbanks, irrigation and other waterways, around large outdoor billboards, and railway facilities. Many of the compounds of the present invention are useful for the selective control of grass and broadleaf weeds in mixed crop / weed environments because they have selective metabolism in crops versus weeds, selective activity in the region of physiological inhibition in crops and weeds, or selective placement in or within mixed crop / weed environments. As those skilled in the art will recognize, suitably combining selective factors within a single compound or a group of compounds can be readily determined by conventional biological and / or biochemical assays.

[0345] The compounds of the present invention can exhibit resistance to (but are not limited to) the following important crops: alfalfa, barley, cotton, wheat, rapeseed, sugar beet, corn (maize), sorghum, soybeans, rice, oats, pea nuts, vegetables, tomatoes, potatoes, perennial plantation crops (including coffee, cocoa, oil palm, and rubber), sugarcane, citrus fruits, grape seeds, fruit trees, nut trees, bananas, plantain, pineapples, hops, tea plants, and woodlands such as eucalyptus and conifers (e.g., loblolly pine), and turfgrass species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue, and Bermuda grass). The compounds of the present invention may be useful in genetically modified crops or crops that have been bred to incorporate resistance to herbicides, express toxic proteins against invertebrate pests (e.g., Bacillus thuringiensis toxin), and / or express other useful properties. As those skilled in the art will recognize, not all compounds are equally effective against all weeds. On the other hand, the compounds that are the subject of the present invention are useful for regulating plant growth.

[0346] The compounds of the present invention have herbicidal activity both before and after germination, and control undesirable vegetation by killing or damaging it or inhibiting its growth. The compounds can be usefully applied by various methods, including contacting the undesirable vegetation's environment, such as soil or water, with the stems, leaves or other parts of the undesirable vegetation, or within the area where the undesirable vegetation is growing, or surrounding its seeds or other bulbils. Examples of undesirable vegetation include at least one species selected from the group consisting of grasses and broadleaf weeds. Undesirable vegetation includes annual bluegrass, Tradescantia virginiana, blackgrass, nightshade, cornflower, cactus, cocklebur (Xanthium pensylvanicum), common ragweed, poppy, wild violet, autumn foxtail grass, goosegrass, foxtail grass, guinea grass, white-flowered beggar, herbicide-resistant blackgrass, dwarf wormwood, Italian ryegrass, Datura stramonium, and sorghum halepense. The following are selected: halepense, crabgrass, little seed canarygrass, morning glory, knotweed, dwarf morning glory, sedge, ryegrass, blue amaranth, shutter cane, shepherd's purse, silky windgrass, sunflower (as a potato weed), buckwheat vine (Polygonum convolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua), red oat, golden foxtail, and leaf-leaf daylily (Cyperus esculentus).

[0347] The effective amount of the compound of the present invention as a herbicide is determined by several factors, including: the selected formulation, the application method, the amount and type of vegetation present, and the growth conditions. Generally, the effective amount of the compound of the present invention as a herbicide is in the range of about 0.001 to 20 kg / ha, preferably about 0.004 to 1 kg / ha. Those skilled in the art can easily determine the effective amount of herbicide necessary to achieve a desired level of weed control.

[0348] In one general embodiment, the compounds of the Disclosure are typically applied, in the form of a formulated composition, to an area containing desirable vegetation (e.g., crops) and undesirable vegetation (i.e., weeds) in contact with a growing medium (e.g., soil) (both of which may be seeds, seedlings, and / or more mature plants). In this area, the composition containing the compounds of the Disclosure can be applied directly, in particular, to the plants or parts thereof of the undesirable vegetation and / or to the growing medium in contact with those plants.

[0349] Desired plant varieties and cultivars of habitats treated with the compounds of this disclosure can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants (transgenic plants) are those in which a different gene (introduced gene) is stably incorporated into the plant genome. An introduced gene, defined by its specific location in the plant genome, is referred to as a transformation or transgenic event.

[0350] Genetically modified plant varieties at loci that can be treated according to the present invention include those that are resistant to one or more biological stresses (harmful organisms such as nematodes, insects, mites, and fungi) or abiotic stresses (such as drought, low temperatures, and soil salinity), or that possess other desirable characteristics. Plants can be genetically modified to exhibit characteristics such as herbicide resistance, insect resistance, altered oil profiles, or drought tolerance.

[0351] Most typically, the compounds of the present invention are used to control undesirable vegetation, but by bringing desired vegetation into contact with the compounds of the present invention in the treated area, superadditive or synergistic effects may be obtained, including the genetic characteristics of the desired vegetation and those incorporated through genetic modification. For example, resistance to herbivorous pests or plant diseases, or resistance to biological / abiotic stress or storage stability, may be greater than would be expected from the genetic characteristics of the desired vegetation.

[0352] The compounds of the present invention may further be mixed with one or more other bioactive compounds or agents to form a multi-component biocide that provides an even broader agricultural protection spectrum, such as: herbicides, herbicide toxicity reducers, fungicides, insecticides, nematicides, fungicides, miticides, growth regulators such as insect molting inhibitors and rooting stimulants, chemical sterilizers, signaling chemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other bioactive compounds, or entomopathogenic bacteria, viruses, or fungi. Mixtures of the compounds of the present invention with other herbicides can broaden the activity spectrum against further weed species and suppress the growth of various resistant biotypes. Accordingly, the present invention also relates to compositions comprising the compound of Formula 1 (in an effective amount as a herbicide) and at least one further bioactive compound or agent (in a biologically effective amount), and may further comprise at least one surfactant, solid diluent, or liquid diluent. Other biologically active compounds or agents may be incorporated into a composition comprising at least one of a surfactant, a solid diluent, or a liquid diluent. The mixture of the present invention may be formed by incorporating one or more other biologically active compounds or agents together with the compound of Formula 1 to form a premix, or by incorporating one or more other biologically active compounds or agents separately from the compound of Formula 1, and then combining the mixture before application (for example, in a spray tank), or by other means, by sequential application.

[0353] A mixture of one or more of the following herbicides and the compounds of the present invention may be particularly useful for weed control: acetochlor, acyfluorphen and its sodium salt, acroniphen, acrolein (2-propenal), alachlor, alloxidim, ametrin, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralide, amitorol, ammonium sulfamate, anirophos, ashram, atrazine, azimsulfuron, beflubutamide, Beflubutamide-M, Benazoline, Benazoline-ethyl, Bencarbazone, Benfluralin, Benfresate, Bensulfuron-methyl, Benslide, Bentazone, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Viranafos, Bispiribac and its sodium salts, Bixlozone, Bromacil, Bromobutide, Bromophenoxime, Bromoxynyl, Bromoxynyl octanoate, Butachlor, Butaphenacil, Butamiphos, Buttraline, Butroquididime, Butyrate, Cafenstrol, Carbetamide, Carfentrazone -Ethyl, Catechin, Chlomethoxyfen, Chloramben, Chlorbromulone, Chlorflurenol-methyl, Chloridazone, Chlorimulone-ethyl, Chlorotolurone, Chlorpropham, Chlorsulfurone, Chlortal-dimethyl, Chlorthiamide, Synidone-ethyl, Symmethiline, Synosulfurone, Clasiphos, Crehoxidim, Cretodim, Clodinafop-propargyl, Chromazon, Clomeprop, Clopyralide, Clopyralide-olamine, Chloranslam-methyl, Cumilon, Cyanazine, Cycloate, Cyclopyrimolate, Cyclo Rosulfamurone, cycloxidium, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and their dimethylammonium, diolamine and trolamine salts, dimuron, darapon, darapon sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedifam, desmethrin, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, diclobenyl, dichlorprop, diclofop-methyl, diclothram,Diphenzocort methyl sulfate, diflufenican, diflufenzopyr, dimeflon, dimepiperate, dimesulfazet, dimetachlor, dimethametrin, dimethenamide, dimethenamide-P, dimethipine, dimethylarsinic acid and its sodium salts, dinitramine, dinoterb, diphenamide, diquatodibromide, dithiopyr, diuron, DNOC, endotal, EPTC, epiriphenacil, esprocarb, ethalfluralin, etamethulfuron-methyl, ethidine, etofumesate, ethoxyphen, ethoxysulfuron, etobe Nzanide, phenoxaprop-ethyl, phenoxaprop-P-ethyl, phenoxasulfone, fenquinotrione, phentrazamide, fenulon, fenulon-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florathlam, fluadifop-butyl, fluadifop-P-butyl, fluazolate, flucetosulfuron, flucloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetulam, flumimicrolac-pentyl, flumio Xazazine, fluomethurone, fluoroglycofen-ethyl, flupoxam, flupyrusulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, flulidone, flulochloridone, fluroxypyr, flulutamon, flutiaceto-methyl, fomesafen, horamsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and ammonium, isopropylammonium, potassium, sodium (including sesquisodium), and trimethium (also known as sulfosate), etc. Its salts, haloxifen, haloxifen methyl, halosulfuron-methyl, haloxyhop-ethotyl, haloxyhop-methyl, hexazinone, hydantosidine, imazametabenz-methyl, imazamox, imazapick, imazapyr, imazakine, imazakine-ammonium, imazetapir, imazetapir-ammonium, imazosulfuron, indanophan, indadiflame, iofensulfuron, iodosulfuron-methyl, ioxinyl, ioxinyl octanoate, ioxinyl-sodium, ifencarbazone, isoproturone,Isouron, isoxaben, isoxaflutol, isoxachlortol, lactofen, renacyl, linuron, maleate hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium, and MCPA-sodium), esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl), and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium), and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, meflu Idide, Mesosulfuron-methyl, Mesotrione, Metam-sodium, Metamihop, Metamitron, Metazachlor, Metazosulfuron, Metabenzuthiazulon, Methylarsonic acid and its calcium, Monoammonium, Monosodium and disodium salts, Methyldimylon, Metobenzulon, Metobromulone, Metrachlor, S-Metrachlor, Metoslam, Metoxlon, Metrivudine, Metosulfuron-methyl, Molinate, Monolinurone, Naproanilide, Napropamide, Napropamide-M, Naptaram, Nebulon, Nicosulfuron, Norf Lurasone olbencarb or tosulfamurone oryzalin, oxaziargyl, oxadiazone, oxasulfuron, oxadiclomefone, oxyfluorphene, paraquat dichloride, pebrate, pelargonic acid, pendimethalin, penoxulam, pentanochlore, pentoxazone, perfluidone, petoxamide, petoxiamide, fenmedifam, picloram, picloram-potassium, picolinafene, pinoxadene, piperofos, pretilachlore, primisulfuron-methyl, prodiamine, profoxidim, prometon, promethrin, Propachlor, propanil, propaxafop, propazine, profam, propisochlor, propoxycarbazone, propyrisulfuron, propizamide, prosulfocarb, prosulfuron, pyraclonil, pyrafulfen-ethyl, pyrasulfolol, pyrazogyl, pyrazolinate, pyrazoxifen, pyrazosulfuron-ethyl, pyribenzoxime, pyributicarb, pyridate, pyrifthalide, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, piroxulam, quinchlorac,Kimmelac, Quinoclamine, Quizalophop-ethyl, Quizalophop-P-ethyl, Quizalophop-P-tefuryl, Limusulfuron, Saflufenacil, Cethoxydim, Sideuron, Simazine, Simetrin, Sulcotrione, Sulfenthrazone, Sulfomethuron-methyl, Sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, Tebutam, Tebuthiuron, Tefuryltrione, Tempotrione, Tepraloxidim, Terbasil, Terbumetone, Terbutyrazine, Terbutrin, Tetoflupyrrolimet, Tenylchlor , thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, thiafenacil, thiocarbasil, torpylate, topramezone, tralkoxydim, trialate, triafamone, triasulfuron, triaziflame, trivenulon-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphan, trietadine, trifloxysulfuron, trifludimoxazine, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2- Chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridine-2(1H)-one, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1-methyl-1H-tetrazole-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3 -b]pyrazine-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (formerly methioxolin), 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,Methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazole-5-yl)-4-(trifluoromethyl)benzamide, and 2-methyl-N-(4-methyl-1,2,5-oxadiazole-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides include Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz.&Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini&Schweinitz) Ditmar:Fries, Phytophthora palmivora (Butl.) Butl., and Puccinia thlaspeos Schub.

[0354] The compounds of the present invention can also be used in combination with plant growth regulators such as abiglycine, N-(phenylmethyl)-1H-purine-6-amine, epocholeon, gibberellic acid, gibberellins A4 and A7, harpin protein, mepicote chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenol, and trinexapac-methyl, as well as with plant growth modifiers such as Bacillus cereus strain BP01.

[0355] General references on agricultural protective agents (i.e., herbicides, herbicide toxicity reducers, insecticides, fungicides, nematicides, acaricides, and biological agents) include: The Pesticide Manual, 13th Edition, CDSTomlin, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2003, and The BioPesticide Manual, 2nd Edition, LGCopping, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2001.

[0356] In embodiments using one or more of these various mixing partners, the mixing partner is typically used in amounts similar to those conventionally used when the partner being mixed is used alone. More specifically, in the mixture, the active ingredient is often applied at application rates between half and all of the application rate specified on the product label for the active ingredient alone. These amounts are described, for example, in the following references: The Pesticide Manual and The BioPesticide Manual. The weight ratios of these various mixing partners (total) to the compound of Formula 1 are typically between approximately 1:3000 and approximately 3000:1. Of particular note are weight ratios between approximately 1:300 and approximately 300:1 (e.g., ratios between approximately 1:30 and approximately 30:1). Those skilled in the art can easily determine the biologically effective amount of the active ingredient required to obtain the desired biological activity spectrum through simple experiments. It will be apparent that including these additional components makes it possible to broaden the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.

[0357] In certain cases, combining the compounds of the present invention with other biologically active (particularly herbicidal) compounds or agents (i.e., active ingredients) can yield a synergistic effect on weeds exceeding the amount added, and / or a less additive effect (i.e., a safety-enhancing effect) on crops or other desirable plants. It is always desirable to reduce the amount of active ingredients released into the environment while effectively controlling pests. It is also desirable to be able to use larger amounts of active ingredients to achieve more effective weed control without causing excessive damage to crops. If a synergistic effect of herbicidal active ingredients occurs in weeds at application rates that provide an agriculturally satisfactory level of weed control, such combinations can be advantageous in lowering crop production costs and reducing the environmental burden. If safety-enhancing of herbicidal active ingredients occurs in crops, such combinations can be advantageous in reducing competition with weeds and enhancing crop protection.

[0358] Of particular note are the combinations of the compounds of this disclosure with at least one other herbicidal active ingredient. Of particular note are combinations in which these other herbicidal active ingredients have a different site of action than the compounds of the present invention. In certain cases, a combination with at least one other herbicidal active ingredient having a similar control spectrum but a different site of action would be particularly advantageous for resistance management. Therefore, the compositions of the present invention may further contain (in an effective amount as a herbicide) at least one additional herbicidal active ingredient having a similar control spectrum but a different site of action.

[0359] The compounds of the present invention can also be used in combination with herbicide toxicity mitigators, such as the following, to increase safety for certain crops: aridochlor, benoxacol, croquintoset-mexyl, cumylon, siomethrinyl, cyprosulfonamide, dimuron, dichlormid, dicyclonone, diethrate, dimepiperate, fenchlorazole-ethyl, fenchlorim, flurazole, fluxofenim, flirazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthal anhydride (1,8-naphthalic anhydride), oxavethrinyl, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate ethyl, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and 3-oxo-1-cyclohexane-1-yl 1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone, and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide. An additional effective amount of herbicide toxicity mitigator may be applied simultaneously with the compounds of the present invention or as a seed treatment. Accordingly, aspects of the present invention relate to herbicide mixtures containing the compound of the present invention and an effective amount of herbicide toxicity mitigator. Seed treatment is particularly useful for selective weed control because it limits the detoxification effect on crops.Therefore, a particularly useful embodiment of the present invention is a method for selectively controlling the proliferation of undesirable vegetation in a crop, comprising contacting an area of ​​the crop with an effective amount of the compound of the present disclosure as a herbicide, thereafter treating the seeds from which the crop grows with an effective amount of a toxicity mitigator. The effective amount of the toxicity mitigator can be easily determined by simple experiments by those skilled in the art.

[0360] The compounds of the present invention may further be mixed with: (1) polynucleotides, including, but not limited to, DNA, RNA, and / or chemically modified nucleotides that affect the amount of a particular target through downregulation, interference, repression, or silencing of genetically modified transcripts that confer herbicidal effects; or (2) polynucleotides, including, but not limited to, DNA, RNA, and / or chemically modified nucleotides that affect the amount of a particular target through downregulation, interference, repression, or silencing of genetically modified transcripts that confer toxicity mitigation effects.

[0361] Of particular note are compositions comprising at least one further active ingredient selected from the group consisting of the compounds of the present disclosure (in an effective herbicidal amount), other herbicides and herbicide toxicity mitigators (in an effective amount), and at least one component selected from the group consisting of surfactants, solid excipients and liquid excipients.

[0362] Preferably for better control of undesirable vegetation (e.g., lower usage rates due to additive effects, a broader spectrum of controlled weeds, or improved crop safety) or for preventing the emergence of resistant weeds are the compounds of the present invention and atrazine, azimsulfuron, beflubutamide, S-beflubutamide, benzisothiazolinone, carfentrazon-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, chromazon, clopyralidopotassium, chloranslam-methyl, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (CA number 81777-95-9) and 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone It is a mixture of herbicides selected from the group consisting of (CA number 81778-66-7) etamethosulfuron-methyl, flumezuram, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,4H)-dione, flupirsulfuron-methyl, fluthiaset-methyl, homesafen, imazetapyr, renacil, mesotrione, metrivudine, metosulfuron-methyl, petoxamide, picloram, pyroxasulfone, quinchlorac, limsulfuron, linzcore, S-methrachlor, sulfenthrazone, thifensulfuron-methyl, triflusulfuron-methyl, and tribenulon-methyl.

[0363] Table A1 lists specific combinations of component (a) and component (b) illustrating the mixtures, compositions, and methods of the present invention. The compound numbers in the component (a) column are identified in Index Table A. The second column of Table A1 lists specific component (b) compounds (e.g., "2,4-D" in the first row). The third, fourth, and fifth columns of Table A1 list a series of weight ratios of component (a) compounds to component (b) that are typically applied to field crops (i.e., (a):(b)). Thus, for example, the first row of Table A1 specifically discloses that the combination of component (a) (i.e., compound 45 in Index Table A) and 2,4-D is typically applied in weight ratios of 1:192 to 6:1. The remaining rows of Table A1 are interpreted similarly.

[0364] [Table 33]

[0365] [Table 34]

[0366] [Table 35]

[0367] [Table 36]

[0368] [Table 37]

[0369] [Table 38]

[0370] [Table 39]

[0371] Table A2 is structured the same as Table A1 above, except that the content under the column heading "Component (a)" is replaced with the content of each component (a) column as shown below. The compound numbers in the component (a) column are identified in Index Table A. Thus, for example, in Table A2, all the content under the column heading "Component (a)" lists "Compound 2" (i.e., Compound 2 identified in Index Table A), and the first row under the column heading in Table A2 specifically discloses a mixture of compound number 2 and 2,4-D. Tables A3 to A64 are structured similarly.

[0372] [Table 40]

[0373] Preferably for better control of undesirable vegetation (e.g., lower usage rates due to enhanced efficacy, a broader spectrum of controlled weeds, or improved crop safety) or for preventing the emergence of resistant weeds, is a mixture of the compound of the present invention with a herbicide selected from the group consisting of chlorimulone-ethyl, nicosulfuron, mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribeurone, pyroxasulfone, pinoxadene, tembotrione, piroxulam, metrachlor, and S-metrachlor.

[0374] The following tests demonstrate the effectiveness of the compounds of the present invention in controlling specific weeds. However, the weed control achieved by the compounds is not limited to these species. See Index Table A for a description of the compounds. In the following index table, the following abbreviations are used: t = tertiary, s = secondary, n = normal, i = iso, c = cyclo, Me = methyl, Et = ethyl, Pr = propyl, i-Pr = isopropyl, Bu = butyl, c-Pr = cyclopropyl, c-Bu = cyclobutyl, c-Pen = cyclopentyl, t-Bu = tert-butyl, i-Bu = isobutyl, Ph = phenyl, OMe = methoxy, OEt = ethoxy, SMe = methylthio, SEt = ethylthio, -CN = cyano, -NC2 = nitro, TMS = trimethylsilyl, allyl = CH2CH=CH2, propargyl = CH2C≡CH, and naphthyl = naphthalenyl. Several other structures are defined in the table below. [ka]

[0375] (R) or (S) indicates the absolute chirality of the chiral carbon center. The abbreviation "(d)" indicates that the compound appeared to decompose upon melting. The abbreviation "Cmpd.#" is an abbreviation for "compound number". The abbreviation "Ex." is an abbreviation for "example," followed by a number indicating the example in which the compound was prepared. The mass spectrum shows the parent ion with the highest isotopic abundance and H to the molecule. + The molecular weight of (M+1), formed by the addition of (Molecular Weight 1), is reported with an estimated accuracy of within ±0.5 Da and is observed using atmospheric pressure chemical ionization (AP+).

[0376] [Table 41]

[0377] [Table 42] [ka]

[0378] [Table 43]

[0379] [Table 44]

[0380] [Table 45]

[0381] Biological embodiments of the present invention Test A Barnyard grass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), corn (Zea mays), giant foxtail (Setaria faberi), goosegrass (Eleusine indica), kochia scoparia, wild oat (Avena fatua), palmer amaranth (Amaranthus palmeri), redroot pigweed (Amaranthus retroflexus), ragweed (Ambrosia artemisiifolia), Italian ryegrass (Lolium multiflorum), soybean (Glycine max), and wheat (Triticum). Seeds of plant species selected from *Aestivum* were planted in a blend of loam and sand and pre-treated with directed soil spraying using a test chemical compound formulated in a non-phytotoxic solvent mixture containing a surfactant.

[0382] Simultaneously, these crops and weed species, as well as plants selected from catchweed bedstraw (Galium aparine) and Erigeron canadensis, were planted in pots containing the same blend of loam and sand and treated with post-emergence application of the same type of test chemical. The plants were 2–10 cm tall and at the one-leaf to two-leaf stage for post-emergence treatment. Treated plants and untreated controls were maintained in a greenhouse for 10 days, after which all treated plants were compared to untreated controls and visually assessed for damage. The plant responses summarized in Table A are graded on a scale of 0–100, where 0 is no effect and 100 is complete control. A dash (-) indicates no test result. Simultaneously, these crops and weed species, as well as plants selected from catchweed bedstraw (Galium aparine) and Erigeron canadensis, were planted in pots containing the same blend of loam and sand and treated with post-emergence application of the same type of test chemical. The plants were 2–10 cm tall and at the one-leaf to two-leaf stage for post-emergence treatment. Treated plants and untreated controls were maintained in a greenhouse for 10 days, after which all treated plants were compared to untreated controls and visually assessed for damage. The plant responses summarized in Table A are graded on a scale of 0–100, where 0 is no effect and 100 is complete control. A dash (-) indicates no test result.

[0383] [Table 46]

[0384] [Table 47]

[0385] [Table 48]

[0386] Test B Plant species selected from barnyard grass (Echinochloa crus-galli), black sandwort (Heteranthera limosa), rice (Oryza sativa), and small-flower umbrella sedge (Cyperus difformis) were grown to the two-leaf stage for the flooded paddy field experiment. At the time of treatment, the test pots were flooded to 3 cm above the soil surface, and the test compound was applied directly to the paddy field water, which was then maintained at that water depth for the duration of the experiment. After maintaining the treated plants and controls in a greenhouse for 10–14 days, all species were visually evaluated in comparison to the controls. The plant responses summarized in Table B are graded on a scale of 0–100, where 0 represents no effect and 100 represents complete control. A dash (-) indicates no test result.

[0387] [Table 49]

[0388] Test C Seeds of plant species selected from blackgrass (Alopecurus myosuroides), corn (Zea mays), giant foxtail (Setaria faberi), goosegrass (Eleusine indica), kochia scoparia, wild oat (Avena fatua), palmer amaranth (Amaranthus palmeri), ragweed (Ambrosia artemisiifolia), Italian ryegrass (Lolium multiflorum), soybean (Glycine max), and wheat (Triticum aestivum) were planted in a blend of loam and sand and pre-treated with directed soil spraying using a test chemical formulated in a non-phytotoxic solvent mixture containing a surfactant.

[0389] Simultaneously, these crops and weed species, as well as plants selected from catchweed bedstraw (Galium aparine) and Erigeron canadensis, were planted in pots containing the same blend of loam and sand and treated with post-emergence application of the same type of test chemical. The plants were 2–10 cm tall and at the one-leaf to two-leaf stage for post-emergence treatment. Treated plants and untreated controls were maintained in a greenhouse for 10 or 12 days, after which all treated plants were compared to untreated controls and visually assessed for damage. The plant response grading summarized in Table A is on a scale of 0–100, where 0 is no effect and 100 is complete control. A dash (-) indicates no test result.

[0390] [Table 50]

[0391] [Table 51]

[0392] [Table 52]

[0393] [Table 53]

[0394] [Table 54]

[0395] [Table 55]

[0396] [Table 56]

[0397] Test D Plant species selected from barnyard grass (Echinochloa crus-galli), black sand vine (Heteranthera limosa), rice (Oryza sativa), and small-flower umbrella sedge (Cyperus difformis) were grown to the two-leaf stage for the flooded paddy field experiment. At the time of treatment, the test pots were flooded to 3 cm above the soil surface, and the test compound was applied directly to the paddy field water, which was then maintained at that water depth for the duration of the experiment. After maintaining the treated plants and controls in a greenhouse for 13 days, all species were visually evaluated in comparison to the controls. The plant responses summarized in Table B are graded on a scale of 0 to 100, where 0 represents no effect and 100 represents complete control. A dash (-) indicates no test result.

[0398] [Table 57]

[0399] Table 58

Claims

1. A compound of formula 1, or its stereoisomer, N-oxide, or salt, 【Chemistry 1】 During the ceremony, R 1 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 2 ~C 6 Alkenil, C 2 ~C 6 Al Quinyl, C 3 ~C 7 Cycloalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenyl, C 3 ~C 7 Haloalkynyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~ C 7 Alkoxy, C 1 ~C 5 Alkylthio, C 2 ~C 3 Alkoxycarbonyl, or C 2 ~C 7 It is a haloalkoxyalkyl; R 2 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 1 ~C 7 Haloalkyl, C 1 ~C 7 a Lucoxy, or C 1 ~C 5 It is alkylthio; R 3 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 2 ~C 6 Alkenil, C 2 ~C 7 Al Kinil, C 3 ~C 7 Cycloalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 3 ~C 7 Haloalkynyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~ C 7 Alkoxy, C 1 ~C 5 Alkylthio, C 2 ~C 3 Alkoxycarbonyl, or C 2 ~C 7 It is a haloalkoxyalkyl; R 4 が、H、C(=O)R 14 、-C(=S)R 14 ,-CO 2 R 14 、-C(=O)R 14 ,-S(O) 2 R 14 、C(=O)NR 13 R 14 ,-S(O) 2 NR 13 R 14 、H 2 OC(=O) OR 14 ,CH 2 OC(=O)NR 13 R 14 , or CH 2 OC(=O)R 14 ; or propal It is gil, allyl, or benzyl; R 5 is H, C 2 -C 6 alkenyl, C 2 -C 7 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 4 cyanoalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 haloalkoxy, C 2 -C 7 alkoxyalkyl, or C 4 -C 7 alkylcycloalkyl; R 6 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 1 ~C 5 Alkylthio, C 2 ~C 3 a Lucoxycarbonyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, C 1 ~C 7 Haloalkoxy, C 2 ~C 7 Haloalkoxyalkyl or C 4 ~C 7 It is alkylcycloalkyl; R 7 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 1 ~C 5 Alkylthio, C 2 ~C 3 a Lucoxycarbonyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, C 1 ~C 7 Haloalkoxy, C 2 ~C 7 Haloalkoxyalkyl or C 4 ~C 7 It is alkylcycloalkyl; R 8 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, C 1 ~C 7 Haloalkoxy, C 2 ~C 7 Alkoxyalkyl, or C 4 ~C 7 It is alkylcycloalkyl; Q is CHR 9 , O, or direct bond; R 9 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 1 ~C 5 Alkylthio, C 2 ~C 3 a Lucoxycarbonyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, C 1 ~C 7 Haloalkoxy, C 2 ~C 7 Alkoxyalkyl, C 2 ~C 7 Haloalkoxyalkyl or C 4 ~C 7 It is alkylcycloalkyl; G is OR 10 is; or G and R 5 But together N-OR 15 It forms; R 10 However, H, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 3 ~C 7 Halocycloalkyl, C 4 ~C 7 Alkylcycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 4 ~C 7 Halocycloalkylalkyl, C 5 ~C 7 Alkylcycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 6 Nitroalkyl, C 3 ~C 6 Alkylcarbonyl Lukil, C 3 ~C 6 Alkoxycarbonylalkyl, C 2 ~C 7 Haloalkoxyalkyl, benzyl, or C 3 ~C 6 It is an alkylcarbonylalkoxy; or R 10 However, the basis of the following equation 【Chemistry 2】 Selected from the group consisting of, R 11 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 7 Haloalkyl, C 2 ~C 7 Hello Lukenil, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, C 1 ~C 7 Haloalkoxy, C 2 ~C 7 Alkoxyalkyl, or C 4 ~C 7 It is alkylcycloalkyl; R 12 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, or C 7 It is a haloalkyl; Each R 13 and R 14 However, independently, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkylalkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy; C 2 ~C 7 Alkoxyalkyl, C 4 ~C 7 Alkylcycloalkyl, Ph, or benzyl; R f However, C 1 ~C 7 It is a haloalkyl; G and R 8 However, it can be linked to any ring carbon having available valence, and the ring is a cyclic amide ring represented by formula 1; Each R 11 or R 12 However, it can be linked to any ring carbon having available valence, and the ring is R 10 -1 to R 10 As shown by -16; R 15 However, H, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenil, C 2 ~ C 6 Alkinyl, or C 4 ~C 7 It is a cycloalkylalkyl; The compound of formula 1, or its stereoisomer, N-oxide, or salt.

2. Q is a direct connection; R 1 However, H, C 1 ~C 7 Alkyl, halogen, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl , C 3 ~C 7 Cycloalkyl, or C 1 ~C 7 It is a haloalkyl; R 2 However, H, C 1 ~C 7 It is an alkyl, halogen, or CN; R 3 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkyl; R 4 が、H、C(=O)R 14 、-C(=S)R 14 ,-CO 2 R 14 、-C(=O)R 14 ,-S(O) 2 R 14 、C(=O)NR 13 R 14 ,-S(O) 2 NR 13 R 14 、H 2 OC(=O) OR 14 ,CH 2 OC(=O)NR 13 R 14 , or CH 2 OC(=O)R 14 And; R 5 However, H, C 2 ~C 6 Alkenil, C 2 ~C 7 Haloalkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 7 Alkoxyalkyl , or C 4 ~C 7 It is alkylcycloalkyl; R 6 However, H, C 1 ~C 7 Alkyl, C 3 ~C 7 Cycloalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 7 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 8 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; G is OR 10 And; R 10 However, H, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 3 ~C 7 Halocycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 4 ~C 7 Halocycloalkylalkyl, C 5 ~C 7 Alkylcycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 3 ~C 7 Alkylthioalkyl, C 2 ~ C 7 Haloalkoxyalkyl, benzyl, or C 4 ~C 7 It is alkylcycloalkyl; R 11 However, H or C 1 ~C 7 It is alkyl; R 12 However, H or C 1 ~C 7 It is alkyl; Each R 13 and R 14 However, independently, H, C 1 ~C 7 Haloalkyl, or C 1 ~C 7 It is alkyl; R f C 1 ~C 3 It is a haloalkyl; The compound according to claim 1.

3. R 1 However, H, C 1 ~C 3 Alkyl, halogen, or C 3 ~C 4 It is a cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3 However, H, Me, F, Cl, -CN, OMe, or CF 3 And; R 4 が、H、SO 2 CF 3 、SO 2 CH 3 、CO 2 Me、COMe、CH 2 OCO-t-Bu ,CH 2 OCO-n-Bu, CH 2 OCO-c-hexyl, CH 2 OCO-c-pentyl CH 2 OCOCH 2 CH 3 , COMe, CH 2 OCOP h, CH 2 OCO-i-Bu, CH 2 OCOMe, CH 2 OCO-sec-Bu, CH 2 OCO-n-Pr and CH 2 OCO-i- Pr, or (C=O)SMe; R 5 However, H, C 4 ~C 7 Cycloalkylalkyl, or C 2 ~C 7 Alkoxyalkyl the law of nature; R 6 However, H, C 1 ~C 7 Alkyl, or C 1 ~C 7 It is an alkoxy; R 7 However, H, C 1 ~C 7 Alkyl, C 3 ~C 7 Cycloalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 8 However, H, C 1 ~C 7 Alkyl, or C 1 ~C 7 It is an alkoxy; G is OR 10 And; R 10 However, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 3 ~ C 7 Halocycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 4 ~C 7 Halocycloalki Alkyl, C 5 ~C 7 Alkylcycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 3 ~C 7 Alkylthioalkyl, benzyl, or C 4 ~C 7 It is alkylcycloalkyl; The compound according to claim 2.

4. R 1 However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH 2 OCOR 14 , or -S(O) 2 R 14 And; R 5 However, it is H; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; G is OR 10 And; R 10 However, H, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 4 ~C 7 Halocycloalkylalkyl, or C 4 ~C 7 It is alkylcycloalkyl; The compound according to claim 3.

5. Q is CHR 9 And; R 1 However, H, C 1 ~C 7 Alkyl, halogen, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl , C 3 ~C 7 Cycloalkyl, C 1 ~C 7 It is a haloalkyl; R 2 However, H, C 1 ~C 7 It is an alkyl, halogen, or CN; R 3 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkyl; R 4 が、H、C(=O)R 14 、-C(=S)R 14 ,-CO 2 R 14 、-C(=O)R 14 ,-S(O) 2 R 14 、C(=O)NR 13 R 14 ,-S(O) 2 NR 13 R 14 、H 2 OC(=O) OR 14 ,CH 2 OC(=O)NR 13 R 14 , or CH 2 OC(=O)R 14 And; R 5 However, H, C 2 ~C 6 Alkenil, C 2 ~C 7 Haloalkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 7 Alkoxyalkyl , or C 4 ~C 7 It is alkylcycloalkyl; R 6 However, H, C 1 ~C 7 Alkyl, C 3 ~C 7 Cycloalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 7 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 8 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; G is OR 10 And; R 9 However, H, C 1 ~C 7 Alkyl, C 3 ~C 7 Cycloalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 10 However, H, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 3 ~C 7 Halocycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 4 ~C 7 Halocycloalkylalkyl, C 5 ~C 7 Alkylcycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 3 ~C 7 Alkylthioalkyl, C 2 ~ C 7 Haloalkoxyalkyl, benzyl, or C 4 ~C 7 It is alkylcycloalkyl; R 11 However, H, or C 1 ~C 7 It is alkyl; R 12 However, H, or C 1 ~C 7 It is alkyl; Each R 13 and R 14 However, independently, H, C 1 ~C 7 Haloalkyl, or C 1 ~C 7 It is alkyl; R f but 1 ~C 3 It is a haloalkyl; The compound according to claim 1.

6. R 1 However, H, C 1 ~C 3 Alkyl, halogen, or C 3 ~C 4 It is a cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3 However, H, Me, F, Cl, -CN, OMe, or CF 3 And; R 4 However, H, SO 2 CF 3 SO 2 CH 3 CO 2 Me, COMe, CH 2 OCO-t-Bu, CH 2 OCO-n-Bu, CH 2 OCO-c-hexyl, CH 2 OCO-c-pentyl, CH 2 OCOCH 2 CH 3 COMe, CH 2 OCOPh, CH 2 OCO-i-Bu, CH 2 OCOMe, CH 2 OCO-sec-Bu, CH 2 OCO-n-Pr and CH 2 It is OCO-i-Pr, or (C=O)SMe; R 5 However, H, C 4 ~C 7 Cycloalkylalkyl, or C 2 ~C 7 It is an alkoxyalkyl; R 6 However, H, C 1 ~C 7 Alkyl or C 1 ~C 7 It is an alkoxy; R 7 However, H, C 1 ~C 7 Alkyl, C 3 ~C 7 Cycloalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 8 However, H, C 1 ~C 7 Alkyl, or C 1 ~C 7 It is an alkoxy; G is OR 10 And; R 9 However, H, C 1 ~C 7 Alkyl, or C 1 ~C 7 It is an alkoxy; R 10 However, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 3 ~C 7 Halocycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 4 ~C 7 Halocycloalkylalkyl, C 5 ~C 7 Alkylcycloalkylalkyl, C 2 ~C 4 Cyanoalkyl, C 3 ~C 7 Alkylthioalkyl, or C 4 ~C 7 It is alkylcycloalkyl; The compound according to claim 5.

7. R 1 However, H, C 1 ~C 7 Alkyl, halogen, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 1 ~C 7 It is a haloalkyl; R 2 However, H, C 1 ~C 7 It is an alkyl, halogen, or CN; R 3 However, H, C 1 ~C 7 Alkyl, halogen, CN, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkyl; R 4 が、H、C(=O)R 14 、-C(=S)R 14 ,-CO 2 R 14 、-C(=O)R 14 、 -S(O) 2 R 14 、C(=O)NR 13 R 14 、-S(O) 2 NR 13 R 14 、CH 2 OC(=O)OR 14 、CH 2 OC(=O)NR 13 R 14 、or CH 2 OC(=O)R 14 where; R 6 However, H, C 1 ~C 7 Alkyl, C 3 ~C 7 Cycloalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 7 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 3 ~C 7 Alkenylalkyl, C 3 ~C 7 Alkynylalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 8 However, H, C 1 ~C 7 Alkyl, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 3 ~C 7 Cycloalkyl, C 2 ~C 4 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Haloalkenil, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; G and R 5 are combined to form N-OR 15 ; R 11 However, H or C 1 ~C 7 It is alkyl; R 12 However, H or C 1 ~C 7 It is alkyl; Each R 13 and R 14 However, independently, H, C 1 ~C 7 Haloalkyl, or C 1 ~C 7 It is alkyl; R f C 1 ~C 3 It is a haloalkyl; R 15 However, H, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenil, C 2 ~ C 6 Alkinyl, or C 4 ~C 7 It is a cycloalkylalkyl; The compound according to claim 1.

8. The compound according to claim 7, wherein Q is a direct bond.

9. R 1 However, H, C 1 ~C 3 Alkyl, halogen, or C 3 ~C 4 It is a cycloalkyl; R 2 However, it is H, Me, F, Cl, or CN; R 3 However, H, Me, F, Cl, -CN, OMe, or CF 3 And; R 4 However, H, SO 2 CF 3 SO 2 CH 3 CO 2 Me, COMe, CH 2 OCO-t-Bu, CH 2 OCO-n-Bu, CH 2 OCO-c-hexyl, CH 2 OCO-c-pentyl CH 2 OCOCH 2 CH 3 COMe, CH 2 OCOPh, CH 2 OCO-i-Bu, CH 2 OCOMe, CH 2 OCO-sec-Bu, CH 2 OCO-n-Pr and CH 2 It is OCO-i-Pr, or (C=O)SMe; R 6 However, H, C 1 ~C 7 Alkyl or C 1 ~C 7 It is an alkoxy; R 7 However, H, C 1 ~C 7 Alkyl, C 3 ~C 7 Cycloalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, or C 1 ~C 7 It is a haloalkoxy; R 8 However, H, C 1 ~C 7 Alkyl, or C 1 ~C 7 It is an alkoxy; The compound according to claim 7 or 8.

10. R 1 However, it is H, Me, halogen, or cyclopropyl; R 2 However, it is either H or F; R 3 However, it is either Me or F; R 4 However, H, CH 2 OCOR 14 , or -S(O) 2 R 14 And; R 6 However, it is H, Me, or OMe; R 7 However, it is H, Me, or OMe; R 8 However, it is H, Me, or OMe; The compound according to claim 9.

11. N-[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (compound 6);[[5-[3-(cyclopentyloxy)-2-oxo-1-pyrrolidinyl]-2,4- Dimethylphenyl][(trifluoromethyl)sulfonyl]aminomethyl 2,2-dimethylpropanoate (compound 5); N-[2,4-dimethyl-5-[2-oxo-3-(2-propyne-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-trifluoromethanesulfonamide (compound 1) N-[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (compound 3); [[5-[3-(cyclopropyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (compound 7); [[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate (compound 8); N-[2,4-dimethyl-5-[2-oxo-3-(2-propen-1-yloxy)-1-pyrrolidinyl]phenyl]-1,1,1-trifluoromethanesulfonamide (compound 2); N-[5-[3-(cyclobutyloxy)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (compound 4); N-[5-[3-(ethoxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (compound 12); N-[2,4-dimethyl-5-[2-oxo-3-[(2-propyne-1-yloxy)imino]-1-pyrrolidinyl]phenyl]-1,1,1-trifluoromethanesulfonamide (compound 13); and 1,1,1-trifluoro-N-[5-[3-(methoxyimino)-2-oxo-1-pyrrolidinyl]-2,4-dimethylphenyl]methanesulfonamide (compound 9), A compound according to claim 1, selected from the group consisting of the following.

12. A herbicidal composition comprising the compound described in claim 1, and at least one component selected from the group consisting of surfactants, solid excipients, and liquid excipients.

13. A herbicidal composition comprising the compound described in claim 1, at least one further active ingredient selected from the group consisting of other herbicides and herbicide toxicity mitigaters, and at least one component selected from the group consisting of surfactants, solid excipients and liquid excipients.

14. (a) the compound of claim 1, and (b) (b1) a photosystem II inhibitor, (b2) acetaldehyde (b) Droxy acid synthase (AHAS) inhibitors, (b) Acetyl-CoA carboxylase (ACCase) inhibitors, (b) Auxin mimes, (b) 5-enol-pyruvir schimate-3-phosphate (EPSP) synthase inhibitors, (b) Photosystem I electron diverters, (b) Protoporphyrinogen oxidase (PPO) inhibitors, (b) Glutamine synthetase (GS) inhibitors, (b) Very long-chain fatty acid (VLCFA) elongase inhibitors, (b) Auxin transport inhibitors, (b) Phytoendesaturase (PDS) inhibitors, (b) 4-Hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors (b13) homogentisic acid soranesyltransferase (HST) inhibitor, (b14) cellulose biosynthesis inhibitor, (b15) other herbicides (including mitotic disruptors, organoarsenic compounds, ashrum, bromobutide, simmethyline, cumylon, dazomet, diphenzocort, dimuron, etobenzanide, flurenol, hosamin, hosamin-ammonium, hydantocydin, metam, methyldimuron, oleic acid, oxadiclomefone, pelargonic acid, and bilibuticarb), (b16) herbicide toxicity mitigants, and a further active ingredient selected from salts of compounds (b1) to (b16).

15. A method for suppressing the growth of undesirable vegetation, comprising contacting the undesirable vegetation or its environment with a herbicidally effective amount of the compound described in claim 1.

16. Undesirable vegetation or its environment, and (b1) photosystem II inhibitors, (b2) acetohydr (b) Loxiate synthase (AHAS) inhibitors, (b) Acetyl-CoA carboxylase (ACCase) inhibitors, (b) Auxin mimes, (b) 5-enol-pyruvir schimate-3-phosphate (EPSP) synthase inhibitors, (b) Photosystem I electron diverters, (b) Protoporphyrinogen oxidase (PPO) inhibitors, (b) Glutamine synthetase (GS) inhibitors, (b) Very long-chain fatty acid (VLCFA) elongase inhibitors, (b) Auxin transport inhibitors, (b) Phytoendesaturase (PDS) inhibitors, (b) 4-Hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b) Homogentid The method of claim 15, further comprising contacting at least one further active ingredient selected from (b1) to (b16) a soranesyltransferase (HST) benzoate inhibitor, (b14) a cellulose biosynthesis inhibitor, (b15) other herbicides (including mitotic disruptors, organoarsenic compounds, ashrum, bromobutide, scinmethilin, cumylon, dazomet, diphenzocort, dimuron, etobenzanide, flurenol, hosamine, hosamine-ammonium, hydantocidin, metam, methyldimuron, oleic acid, oxadiclomefone, pelargonic acid, and bilibuticarb), (b16) a herbicide toxicity mitigator, and salts of compounds (b1) to (b16).

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