Substituted haloalkyl sulfonanilide herbicides

Abstract

This invention discloses a compound of formula 1, all its stereoisomers, N-oxides, and salts, wherein G is CONR5R6 or selected from... Furthermore, R1 to R18, Rf, and G are as defined in this invention. This invention also discloses compositions containing compounds of formula 1 and methods for controlling unwanted vegetation, comprising contacting the unwanted vegetation or its environment with an effective amount of a compound or composition of this invention.

Description

Technical Field

[0001] This invention relates to specific haloalkyl sulfonamides, their N-oxides, salts and compositions, and methods for their use in controlling unwanted vegetation. Prior Technology

[0002] Control of unwanted vegetation is crucial for achieving high crop efficiency. Selective control of weed growth is essential, especially for beneficial crops such as rice, soybeans, sugar beets, corn, potatoes, wheat, barley, tomatoes, and cultivated crops. Undetected weed growth in these beneficial crops can lead to a significant decrease in productivity, thereby increasing consumer costs. Control of unwanted vegetation in non-crop areas is also important. Many products are commercially available for these purposes, but there is still a need for novel compounds that are more effective, less costly, less toxic, safer for the environment, or have different sites of action. Summary of the Invention

[0003] This invention relates to formula [1] Compounds, all their stereoisomers, N-oxides and salts, agricultural components containing the like and their use as herbicides: in G is CONR5R6 or selected from G-1 , G-2 , G-3 , G-4 and G-5 ; R1 is 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; R2 is H, C1-C7 alkyl, halogen, CN, C1-C7 haloalkyl, C1-C7 alkoxy, C3-C7 cycloalkyl, or C1-C5 alkylthio; R3 can be H, C1-C7 alkyl, halogen, CN, C2-C6 alkenyl, C2-C7 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; R4 is H, C(=O)R19, -C(=S)R19, -CO2R19, -C(=O)SR19, -S(O)2R19, C(=O)NR19R20, -S( O)2NR19R20, S(OH)2NR19R20, CH2OC(=O)OR19, CH2OC(=O)NR19R20 or CH2OC(=O)R19; R5 can be H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl; R6 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl; or R5 and R6, together with the nitrogen atoms attached thereto, form a 3 to 7-membered ring containing a carbon atom and arbitrarily 1 to 3 oxygen, sulfur, or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O), or S(O)2. The ring is arbitrarily substituted with at most 5 substituents independently selected from (Rv)r, where r is the number of substituents. Rv is independently selected from the group consisting of: H, halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; or When two Rvs are attached to the same carbon atom or to two adjacent carbon atoms, the two Rvs, together with the attached carbon atoms or groups of carbon atoms, can form a 3 to 7-membered ring containing a carbon atom and any 1 to 3 oxygen, sulfur, or nitrogen atoms as ring members, wherein at most two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O), or S(O)2. The ring is unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy. R7 is H, C1-C7 alkyl, halogen, CN, C1-C7 haloalkyl, or C1-C7 alkoxy; R8 is H, C1-C7 alkyl; or R7 and R8 can together form a 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur, or nitrogen atoms as ring members, the ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R9 can be 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 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, or C4-C7 alkylcycloalkyl; R7 and R9 can together form a fused 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur, or nitrogen atoms as ring members, the ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R10 is H or a C1-C7 alkyl group; or R9 and R10 can form a 3- to 7-membered ring with the attached carbon atom, containing a carbon atom and any 1 to 2 oxygen, sulfur, or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O), or S(O)2. The ring is arbitrarily substituted with at most 5 substituents independently selected from (Rv)r, where r is the number of substituents; or When two Rv atoms are attached to the same carbon atom or to two adjacent carbon atoms, the two Rv atoms and the attached carbon atoms or groups of carbon atoms can form a 3 to 7-membered ring, which contains a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2; Q is O, S, CR11R12, or NR13; R11 and R12, together with their attached carbon atoms, form a 3- to 7-membered ring containing a carbon atom and any one or two oxygen, sulfur, or nitrogen atoms as ring members. This ring is either unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; or R9 and R11 together with the attached carbon atom form a 6-membered aromatic ring, which can be arbitrarily substituted with up to 4 independent substituents selected from Rw; Rw is a C1-C7 alkyl, halogen, C1-C7 haloalkyl, or C1-C7 alkoxy; r can be 0, 1, 2, 3, 4, or 5; R13 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl; R14 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C1-C7 thioalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl; R15 is H, C1-C7 alkyl, halogen, C1-C7 haloalkyl, or C1-C7 alkoxy; R16 is H, cyano, C1-C7 alkyl, halogen, C1-C4 alkylthio, C1-C7 haloalkyl, or C1-C7 alkoxy; R17 can be 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; R18 is H, C1-C7 alkyl, halogen, C1-C7 haloalkyl, or C1-C7 alkoxy; R19 is a C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl, C4-C7 alkylcycloalkyl; R20 is H or a C1-C7 haloalkyl group; and Rf is a C1-C7 haloalkyl group.

[0004] More specifically, the present invention relates to formulas [1] Compounds, all stereoisomers thereof, N-oxides or salts. The present invention also relates to herbicidal compositions comprising the compound of the present invention (i.e., in 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 growth of undesirable vegetation comprising contacting vegetation or its environment with a herbicidally effective amount of the compound of the present invention (as described herein).

[0005] The present invention also includes a herbicidal mixture comprising (a) selected from the formula [1] All its stereoisomers, N-oxides and salts, and (b) at least one additional active ingredient selected from (b1) to (b16) and salts of compounds from (b1) to (b16), as described below. Implementation

[0006] The terms “comprising,” “including,” “encompassing,” “having,” “containing,” “comprising,” “characterized in,” or any other variation thereof, as used herein, are intended to cover non-exclusive contents and explicitly indicate any limitations. For example, an composition, mixture, process, method, article, or apparatus containing a list of elements is not necessarily limited to those elements but may include other elements not expressly listed or inherent in such composition, mixture, process, method, article, or apparatus.

[0007] The transitional phrase "composed of" excludes any unspecified elements, steps, or ingredients. If used in the claims, it would exclude the listed materials from the claims, except for impurities typically associated with them. When the phrase "composed of" appears in the body of the claims, rather than immediately following the preamble, it is limited to the elements described in the body; other elements are not excluded from the claims as a whole.

[0008] The transitional phrase "substantially composed of ~" defines, beyond its literal meaning, a composition, method, or apparatus, including materials, steps, features, components, or elements, provided that such additional materials, steps, features, components, or elements do not substantially affect the essential and novel features of the scope of this invention's patent application. The term "substantially composed of ~" falls between "comprising" and "composed of ~".

[0009] It should be understood that, unless otherwise stated, if the applicant defines an invention or part thereof in an open-ended term (such as "comprising"), such description shall be interpreted as also describing such an invention in terms of "substantially composed of" or "composed of".

[0010] Furthermore, unless explicitly stated otherwise, "or" means inclusive "or" rather than exclusive "or". For example, condition A or B is satisfied by any of the following conditions: 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 "one" preceding the elements or components of this invention are intended not to limit the number of instances (i.e., the number of times) of the element or component. Therefore, "a" or "one" should be interpreted as including one or at least one, and the singular form of an element or component also includes the plural form, unless the number is clearly presented in the singular form.

[0012] The term "seedling" as used in this article may be used alone or in combination, referring to a young plant that develops from the embryo of a seed.

[0013] The term "broadleaf" as used herein may be used alone or in words such as "broadleaf weeds" to refer to dicotyledonous or dicotyledonous plants, which is used to describe a group of angiosperms characterized by an embryo having two cotyledons.

[0014] In the above, the term "alkyl," whether used alone or in combination, such as "alkylthio" or "haloalkyl," includes straight-chain or branched alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, or various butyl, pentyl, or hexyl isomers. "Alkenyl" includes straight-chain or branched alkenes, such as vinyl, 1-propenyl, 2-propenyl, and various butenyl, pentenyl, and hexenyl isomers. "Alkenyl" also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. "Alynyl" includes straight-chain or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl, and various butynyl, pentynyl, and hexynyl isomers. "Alynyl" may also include a moiety containing multiple bonds, such as 2,5-hexadiynyl. "Alynylalkyl" indicates alkynyl substitution on an alkyl group. Examples of "alkynylalkyl" include CH≡CCH2, CH3C≡CCH2, CH≡CCH2CH2, CH≡CCH(CH3)CH2, and various alkynylalkyl isomers. "Alkylene" represents a straight-chain or branched alkyl dieny. Examples of "alkylene" include CH2, CH2CH2, CH(CH3), CH2CH2CH2, CH2CH(CH3), and various butene isomers. "Alkenylene" represents a straight-chain or branched alkyl dieny containing one alkene bond. Examples of "alkenylene" include CH=CH, CH2CH=CH, CH=C(CH3), and various butenyl isomers. "Alynylene" represents a straight-chain or branched alkyl dieny containing one alkene bond. Examples of "Alynylene" include C≡C, CH2C≡C, C≡CCH2, and various butynyl isomers.

[0015] "Alkoxy" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, and various butoxy, pentoxy, and hexoxy isomers. "Alkoxyalkyl" represents the substitution of an alkoxy group on an alkyl group. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2, and CH3CH2OCH2CH2. "Alkoxyalkoxy" represents the substitution of an alkoxy group on an alkoxy group. "Alkenoxy" includes straight-chain or branched alkenoxy moieties. Examples of "alkenoxy" include H2C=CHCH2O, (CH3)2C=CHCH2O, (CH3)CH=CHCH2O, (CH3)CH=C(CH3)CH2O, and CH2=CHCH2CH2O. "Alkyneoxy" includes straight-chain or branched alkyneoxy moieties. Examples of "alkyneoxy" include HC≡CCH2O, CH3C≡CCH2O, and CH3C≡CCH2CH2O. "Alkyl thio" includes branched or straight-chain alkyl thio groups, such as methyl thio, ethyl thio, and various propyl thio, butyl thio, pentyl thio, and hexyl thio isomers. "Alkyl sulfinyl" includes two mirror-image isomers of alkyl sulfinyl. Examples of "alkyl sulfinyl" include CH3S(O)-, CH3CH2S(O)-, CH3CH2CH2S(O)-, (CH3)2CHS(O)-, and various butyl sulfinyl, pentyl sulfinyl, and hexyl sulfinyl isomers. Examples of "alkyl sulfinyl" include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and various butyl sulfinyl, pentyl sulfinyl, and hexyl sulfinyl isomers. "alkylthioalkyl" indicates alkylthio substitution on an alkyl group. Examples of "alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2, and CH3CH2SCH2CH2. "alkylthioalkoxy" indicates alkylthio substitution on an alkoxy group. "alkyldithio" indicates a branched or straight-chain alkyl dithio group. Examples of "alkyldithio" include CH3SS-, CH3CH2SS-, CH3CH2CH2SS-, (CH3)2CHSS-, and various butyl and pentyl dithio isomers. "cyanoalkyl" indicates an alkyl group substituted with a cyano group. Examples of "cyanoalkyl" include NCCH2, NCCH2CH2, and CH3CH(CN)CH2. The definitions of "alkylamino", "dialkylamino", "alkenylthio", "alkenylsulfinyl", "alkenylsulfonyl", "alkynylthio", "alkynylsulfinyl", "alkynylsulfonyl" and their analogues are similar to the examples above.

[0016] "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "alkylcycloalkyl" represents alkyl substitution at the cycloalkyl moiety, and includes, for example, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl, and 4-methylcyclohexyl. The term "cycloalkylalkyl" represents substitution at the alkyl moiety of a cycloalkyl group. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moiety bonded to a straight-chain or branched alkyl group. The term "cycloalkoxy" represents a cycloalkyl group connected by a single oxygen atom, such as cyclopentoxy and cyclohexoxy. "Cycloalkylalkoxy" represents a cycloalkylalkyl group attached to an alkyl chain by a single oxygen atom. Examples of "cycloalkylalkoxy" include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moiety bonded to a straight-chain or branched alkoxy group. "Cyanocycloalkyl" represents a cycloalkyl group substituted with a cyano group. Examples of "cyanocycloalkyl" include 4-cyanocyclohexyl and 3-cyanocyclopentyl. "Cycloalkenyl" includes groups such as cyclopentenyl and cyclohexenyl, as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl.

[0017] The term "halogen" is used alone or in combination (e.g., "halogenated alkyl"), or as a descriptive term such as "alkyl substituted with halogen," including fluorine, chlorine, bromine, or iodine. Furthermore, when used in combination such as "halogenated alkyl," or as a descriptive term such as "halogen-substituted alkyl," the alkyl group may be partially or wholly substituted with a halogen atom (which may be the same or different). Examples of "halogenated alkyl" or "halogen-substituted alkyl" include F3C, ClCH2, CF3CH2, and CF3CCl2. The terms "halogenated cycloalkyl," "halogenated alkoxy," "halogenated alkylthio," "halogenated alkenyl," "halogenated alkynyl," and their analogues are defined similarly to the term "halogenated alkyl." Examples of "halogenated alkoxy" include CF3O-, CCl3CH2O-, HCF2CH2CH2O-, and CF3CH2O-. Examples of "halogenated alkyl thiols" include CCl3S-, CF3S-, CCl3CH2S-, and ClCH2CH2CH2S-. Examples of "halogenated alkyl sulfinylls" include CF3S(O)-, CCl3S(O)-, CF3CH2S(O)-, and CF3CF2S(O)-. Examples of "halogenated alkyl sulfinylls" include CF3S(O)2-, CCl3S(O)2-, CF3CH2S(O)2-, and CF3CF2S(O)2-. Examples of "halogenated alkenylls" include (Cl)2C=CHCH2- and CF3CH2CH=CHCH2-. Examples of "halogenated alkynylls" include HC≡CCHCl-, CF3C≡C-, CCl3C≡C-, and FCH2C≡CCH2-. Examples of "haloalkoxyalkoxy" include CF3OCH2O-, ClCH2CH2OCH2CH2O-, Cl3CCH2OCH2O- and branched alkyl derivatives.

[0018] "Alkyl carbonyl" represents a straight-chain or branched alkyl moiety bonded to a C(=O) group. Examples of "alkyl carbonyl" include CH3C(=O)-, CH3CH2CH2C(=O)-, and (CH3)2CHC(=O)-. Examples of "alkoxy carbonyl" include CH3OC(=O)-, CH3CH2OC(=O)-, CH3CH2CH2OC(=O)-, (CH3)2CHOC(=O)-, and various butoxy- or pentoxy carbonyl isomers.

[0019] The total number of carbon atoms in the substituents is indicated by the prefixes "Ci-Cj", where i and j are numbers 1 to 7. For example, C1-C4 alkylsulfonyl represents methylsulfonyl to butylsulfonyl; C2 alkoxyalkyl represents CH3OCH2-; C3 alkoxyalkyl represents, for example, CH3CH(OCH3)-, CH3OCH2CH2- or CH3CH2OCH2-; and C4 alkoxyalkyl represents various isomers of alkyl groups substituted with alkoxy groups containing a total of four carbon atoms, such as CH3CH2CH2OCH2- and CH3CH2OCH2CH2-.

[0020] When a compound is unsubstituted or substituted with a substituent having a substituent with a subscript (representing the number of substituents), the substituent is independently selected from the defined group of substituents (e.g., [(Rv)r], where r is 0, 1, 2, 3, 4, or 5). For example, when r is 0, it indicates that the compound is unsubstituted, and hydrogen may be located at positions not mentioned in the definitions of various groups. As another example, when r is 2, it indicates that the compound is substituted with two Rv substituents independently selected from the defined substituents.

[0021] When a group contains a substituent that can be hydrogen (such as R1 or R2), it should be understood that when the substituent is taken as hydrogen, this is equivalent to the group being unsubstituted at the specified substituent position. When one or more positions on a group are called "unsubstituted" or "unreplaced", a hydrogen atom is attached to occupy any free valency.

[0022] Unless otherwise stated, [1] The "ring" of the components (such as two Rvs and the carbon atoms attached to them forming a ring) is a carbocyclic or heterocyclic ring. The term "ring member" refers to the atoms or other parts (such as C(=O), C(=S), S(O) or S(O)2) that form the framework of a ring or ring system.

[0023] The terms "carbocycle," "carbocyclic compound," or "carbocyclic system" refer to a ring or ring system in which the atoms forming the ring skeleton are selected only from carbon. Unless otherwise specified, a carbocycle can be saturated, partially unsaturated, or completely unsaturated. A completely unsaturated carbocycle that satisfies Hückel's rule is also called an "aromatic ring." A "saturated carbocycle" means a ring with a skeleton composed of carbon atoms connected by single bonds; unless otherwise specified, the remaining carbon atoms are all occupied by hydrogen atoms.

[0024] The terms "heterocycle," "heterocyclic compound," or "heterocyclic system" refer to a ring or ring system in which at least one atom forming the ring skeleton is not carbon, but rather nitrogen, oxygen, or sulfur. Typically, a heterocycle contains no more than four nitrogen atoms, no more than two oxygen atoms, and no more than two sulfur atoms. Unless otherwise specified, a heterocycle can be saturated, partially unsaturated, or fully unsaturated. When a fully unsaturated heterocycle satisfies Huck's rule, it is also called a "heteroaromatic ring" or "aromatic heterocycle." Unless otherwise specified, heterocycles and heterocyclic systems can be linked by any available carbon or nitrogen atom, replacing a hydrogen atom on that carbon or nitrogen atom.

[0025] "Aromatic" means that each atom in a ring is substantially in the same plane and has p orbitals perpendicular to the ring plane, with (4n + 2)π electrons (where n is a positive integer) associated with the ring to obey Huckell's rule. The term "aromatic ring system" refers to a carbon ring or heterocyclic system in which at least one ring is aromatic. The term "aromatic carbon ring system" refers to a carbon ring system in which at least one ring is aromatic. The term "aromatic heterocyclic system" refers to a heterocyclic system in which at least one ring is aromatic. The term "non-aromatic ring system" refers to a carbon ring or heterocyclic system, which may be fully saturated, and partially or fully unsaturated, provided that no ring in the system is aromatic. The term "non-aromatic carbon ring system" refers to a ring system in which no ring is aromatic. The term "non-aromatic heterocyclic system" refers to a heterocyclic system in which no ring is aromatic.

[0026] The term "arbitrarily substituted" in relation to heterocycles means that the group is unsubstituted or has at least one non-hydrogen substituent that does not eliminate the biological activity of the unsubstituted analog. As used herein, unless otherwise specified, the following definitions apply. The term "arbitrarily substituted" is used interchangeably with "substituted or unsubstituted" or "(un)substituted." Unless otherwise stated, an arbitrarily substituted group may have substituents at each substituted position of the group, and each substitution reaction is independent of the others.

[0027] In the formula In [1], when G is CONR5R6, NR5R6 can be (among the rest) J. Some non-limited instances of J are described in List 1, where each structure is accompanied by a J-#, and # is a number. List 1 J-1 J-2 J-3 J-4 J-5 J-6 J-7 J-8 9 days to go D-10 D-11 D-12 D-13 D-14 15 days to go D-16 D-17 D-18 D-19 20 days to go D-21 D-22 23 days to go 24 days to go 25 days to go D-26 D-27 28 days to go D-29 30 days to go D-31 J-32 J-33 34 days to go 35 days to go J-36 37 days to go J-38 D-39 D-40 D-41 D-42 D-43 D-44 D-45 D-46 D-47 48 days to go J-49 J-50 J-51 J-52 J-53 J-3a* J-3b* J-54 * "a" indicates that the two CH3 parts are in a cis configuration; and "b" indicates that the two CH3 parts are in a trans configuration.

[0028] In the formula In [1], when G is CONR5R6, NR5R6 can also be (among the rest) K. Some non-limited instances of K are described in List 2, where each structure is accompanied by a K-#, and # is a number. List 2 K-1 K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9

[0029] In the formula In [1], when G is G-1, some non-limited instances of G-1 are described in List 3, where each structure is accompanied by a G-1-#, and # is a number. List 3 , , , G-1-1 G-1-1a* G-1-1b* G-1-2 , , , , G-1-3 G-1-4 G-1-5 G-1-6 G-1-7 G-1-8 G-1-8a* G-1-8b* G-1-9 G-1-10 G-1-11 G-1-12 G-1-13 G-1-14 G-1-15 G-1-16 G-1-17 G-1-18 G-1-19 G-1-20 G-1-21 G-1-22 G-1-23 G-1-24 G-1-24a* G-1-24b* G-1-25 G-1-1aa G-1-1ab G-1-26 G-1-27 G-1-28a* G-1-28b* G-1-29 G-1-30 G-1-31 G-1-32 G-1-33 G-1-33a* G-1-33b* G-1-34 G-1-34a* G-1-34b* G-1-35 G-1-35a* G-1-35b* G-1-36 G-1-37 G-1-38 G-1-38a* G-1-38b* G-1-8aa G-1-8ab * "a" indicates that both H atoms are in cis configuration; and "b" indicates that both H atoms are in trans configuration, except for the following compounds; for G-1-33a and G-1-33b, "a" indicates that both Et atoms are in cis configuration, and "b" indicates that both Et atoms are in trans configuration; for G-1-38a and G-1-38b, "a" indicates that H and Me show cis configuration, and "b" indicates that H and Me show trans configuration.

[0030] In the formula In [1], when G is G-2, some non-limited instances of G-2 are described in List 4, where each structure is accompanied by a G-2-#, and # is a number. List 4 G-2-1 G-2-2 G-2-3 G-2-4 G-2-5 G-2-6 G-2-7 G-2-8 G-2-9 G-2-10 G-2-11 G-2-12 G-2-13 G-2-14 G-2-15 G-2-16 G-2-17

[0031] Several synthetic methods are known in this art for preparing aromatic and non-aromatic heterocyclic and cyclic systems; for a comprehensive review, see the eight-volume edition of *Comprehensive Heterocyclic Chemistry*, edited by A.R. Katritzky and C.W. Rees, Pergamon Press, Oxford, 1984, and the twelve-volume edition of *Comprehensive Heterocyclic Chemistry II*, edited by A.R. Katritzky, C.W. Rees, and E. F. V. Scriven, Pergamon Press, Oxford, 1996.

[0032] The compounds of this invention can exist as one or more stereoisomers. Various stereoisomers include mirror-image isomers, non-mirror-image isomers, trans-isomers, and geometric isomers. Stereoisomers are isomers with the same composition but different spatial arrangements of their atoms, and include mirror-image isomers, non-mirror-image isomers, cis-trans isomers (also called geometric isomers), and trans-isomers. Trans-isomers are generated by restricted rotation around a single bond, wherein the rotational barrier is high enough to allow the separation of isomer species. Those skilled in the art will understand that a stereoisomer can be more active and / or exhibit advantageous effects when enriched relative to or separated from other stereoisomers. Furthermore, those skilled in the art are familiar with how to separate, enrich, and / or selectively prepare such stereoisomers. The compounds of this invention can exist as mixtures of stereoisomers, individual stereoisomers, or optically active forms.

[0033] For example, when G is G-1 and R7 and R9 together with their attached carbon atoms form a cyclopentyl ring, the formula... [1] The compound may have at least two stereoisomers. The two stereoisomers are described by formula: [1'] and formula [1"], where the chiral center is marked with an asterisk (*). For a full discussion of all forms of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.

[0034] As another example, when G is CONR5R6, R5 and R6 together with their attached nitrogen atoms form a piperidinyl ring, which has at least one chiral center, as shown in the formula. [1] The compound may have at least two stereoisomers, wherein the chiral center is indicated by an asterisk (*).

[0035] The molecular descriptions presented in this paper follow the standard conventions for describing stereochemistry. To represent stereo configurations, solid wedges represent bonds rising from the plane of the drawing towards the observer, with the wide end of the wedge connected to an atom rising from the plane of the drawing towards the observer. Dashed wedges represent bonds falling below the plane of the drawing away from the observer, with the wide end of the wedge connected to an atom falling away from the observer. Lines of equal width represent bonds with opposite or neutral orientations relative to those shown as solid or dashed wedges; lines of equal width also represent bonds within a molecule or part of a molecule, without attempting to specify a particular stereo configuration.

[0036] This invention comprises racemic mixtures, for example, in equal amounts. [1'] and [1"] mirror isomer or equivalent formula [1'''] and [1"''] mirror isomers. Furthermore, the present invention includes, compared to racemic mixtures, compounds rich in the formula... [1] Mirror isomers of compounds. This invention also includes substantially pure compounds of formula [1]. [1] Mirror isomers of compounds (e.g., formula) [1'] or formula [1"]).

[0037] When enriched on mirror isomers, one mirror isomer is present in greater quantity than the other, and the degree of enrichment can be defined by the excess amount of mirror isomers ("ee"), which is defined as (2x-1)·100%, where x is the molar fraction of the main mirror isomer in the mixture (e.g., 20% ee is equivalent to a 60:40 ratio of mirror isomers).

[0038] Preferably, the composition of the present invention has a more active isomer with at least 50% mirror-image isomer excess; more preferably at least 75% mirror-image isomer excess; even more preferably at least 90% mirror-image isomer excess; and most preferably at least 94% mirror-image isomer excess. Particularly noteworthy are specific embodiments of mirror-image isomer purity of the more active isomer.

[0039] Mode [1] The compound may contain other chiral centers. For example, substituents and other molecular components (such as Rv) may themselves contain chiral centers. The present invention includes racemic mixtures at such other chiral centers as well as enriched and substantially pure stereoconfigurations.

[0040] The compounds of this invention may exist as one or more configurational isomers, and the formula is... [1] Any restricted bond rotation. The present invention comprises mixtures of configurational isomers. Furthermore, the present invention includes compounds rich in one configurational isomer relative to other configurational isomers.

[0041] Mode [1] Compounds typically exist in more than one form, therefore, formula [1] This includes all crystalline and amorphous forms of the compounds represented by them. Amorphous forms include specific examples of solids (such as waxes and gums) and specific examples of liquids (such as solutions and melts). Crystalline forms include specific examples that essentially represent single crystal types and specific examples that represent mixtures of polymorphs (i.e., different crystal types). The term "polymorph" means a chemical compound in a particular crystalline form that can crystallize in different crystalline forms, which have different molecular arrangements and / or configurations in the crystal lattice. Although polymorphs may have the same chemical composition, their compositions may differ due to the presence or absence of weakly or strongly bonded co-crystallized water or other molecules in the crystal lattice. The chemical, physical, and biological properties of polymorphs may differ, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate, and biological availability. Those skilled in the art will understand that, relative to the same formula [1] Another polymorph of the compound or a mixture of polymorphs, formula [1] Homomorphic polymorphs of compounds can exhibit beneficial effects (such as suitability for formulation into useful compounds and improvement of biological properties). Formulas can be realized using methods known to those skilled in the art. [1] Preparation and separation of specific polymorphs of compounds, including, for example, crystallization with selected solvents and temperatures. For a full discussion of polymorphism, see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

[0042] Those skilled in the art will understand that not all nitrogen-containing heterocyclic compounds can form N-oxides, because nitrogen requires a lone pair of electrons to be oxidized into oxides; those skilled in the art will understand that such nitrogen-containing heterocyclic compounds can form N-oxides. Those skilled in the art will also understand that tertiary amines can form N-oxides. Synthetic methods for preparing N-oxides of heterocyclic compounds and tertiary amines are known to those skilled in the art, including the oxidation of heterocyclic compounds and tertiary amines with peroxy acids (such as peracetic acid and m-chloroperoxybenzoic acid (MCPBA)), hydrogen peroxide, alkyl hydrogen peroxides (such as tertiary butyl hydrogen peroxide), sodium perborate, and dioxiranes (such as dimethyldioxiranes). Their methods for preparing N-oxides have been extensively described and reviewed in the literature, see, for example: TL Gilchrist, *Comprehensive Organic Synthesis*, vol. 7, pp. 748-750, SV Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik, *Comprehensive Heterocyclic Chemistry*, vol. 3, pp. 18-20, AJ Boulton and A. McKillop, Eds., Pergamon Press; MR Grimmett and BRT Keene, *Advances in Heterocyclic Chemistry*, vol. 43, pp. 149-161, AR Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik, *Advances in Heterocyclic Chemistry*, vol. 9, pp. 285-291, AR Katritzky and AJ Boulton, Eds., Academic Press; and GWH Cheeseman and ESG... Werstiuk's Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, AR Katritzky and AJ Boulton, Eds., Academic Press.

[0043] Those skilled in the art will understand that, because salts of chemical compounds exist in equilibrium with their corresponding non-salt forms under environmental and physiological conditions, salts possess the biological benefits of their non-salt forms. Therefore, there are various formulas... [1] Salts of the compound can be used to control unwanted vegetation (i.e., agricultural applications). Formula [1] Salts of compounds include acid addition salts containing 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). [1] When the compound contains an acidic moiety (such as a carboxylic acid or a phenol), the salt also includes those that form an organic or inorganic base (such as pyridine, triethylamine or ammonia), or a sodium, potassium, lithium, calcium, magnesium or barium amide, hydride, hydroxide or carbonate. Accordingly, the present invention comprises salts selected from the formula [1] Its N-oxides and salts applicable to agriculture.

[0044] The specific embodiments of the present invention described in the invention summary include the formulas thereof. [1] The compounds are those described in any of the following specific examples:

[0045] Specific Implementation Example 1. One Formula [1] Compounds, their stereoisomers, N-oxides and salts, agricultural components containing the like and their use as herbicides, as described in the invention.

[0046] Specific Example 1a. The compound as in Specific Example 1, wherein G is CONR5R6.

[0047] Specific Example 1b. The compound as in Specific Example 1, wherein G is G-1.

[0048] Specific Example 1c. The compound of Specific Example 1, wherein G is G-2.

[0049] Specific Example 1d. The compound as in Specific Example 1, wherein G is G-3.

[0050] Specific Example 1e. The compound of Specific Example 1, wherein G is G-4.

[0051] Specific Example 1f. The compound of Specific Example 1, wherein G is G-5.

[0052] Specific Implementation Example 2. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R1 is H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl or C1-C7 haloalkyl.

[0053] Specific Example 2a. The compound of Specific Example 2, wherein R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl;

[0054] Specific Example 2b. The compound of Specific Example 2a, wherein R1 is H, C1-C3 alkyl, halogen or C3-C4 cycloalkyl.

[0055] Specific Example 2c. The compound as in Specific Example 2b, wherein R1 is H, Me, halogen or cyclopropyl.

[0056] Specific Example 2d. The compound as in Specific Example 2c, wherein R1 is H, Me, F, Cl, Br or cyclopropyl.

[0057] Specific Example 2e. The compound as in Specific Example 2d, wherein R1 is Me or Cl.

[0058] Specific Example 2f. The compound as in Specific Example 2e, wherein R1 is Me.

[0059] Specific Example 2g. The compound as in Specific Example 2e, wherein R1 is Cl.

[0060] Specific Implementation Example 3. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R2 is H, C1-C7 alkyl, halogen, -CN, C1-C7 haloalkyl, C1-C7 alkoxy, C3-C7 cycloalkyl or C1-C5 alkylthio.

[0061] Specific Example 3a. The compound of Specific Example 3, wherein R2 is H, C1-C7 alkyl, C3-C6 cycloalkyl, halogen or CN.

[0062] Specific Example 3b. The compound of Specific Example 3a, wherein R2 is H, Me, F, Cl or CN.

[0063] Specific Example 3c. The compound as in Specific Example 3b, wherein R2 is H, Me or F.

[0064] Specific Example 3d. The compound as in Specific Example 3c, wherein R2 is H.

[0065] Specific Example 3e. The compound as in Specific Example 3c, wherein R2 is F.

[0066] Specific Example 3f. The compound as in Specific Example 3c, wherein R2 is Me.

[0067] Specific Implementation Example 4. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R3 is H, C1-C7 alkyl, halogen, -CN, C2-C6 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl or C2-C7 haloalkoxyalkyl.

[0068] Specific Example 4a. The compound of Specific Example 4, wherein R3 is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy or C1-C7 haloalkyl.

[0069] Specific Example 4b. The compound as in Specific Example 4a, wherein R3 is H, Me, F, Cl, -CN, OMe or CF3.

[0070] Specific Example 4c. The compound as in Specific Example 4b, wherein R3 is Me or F.

[0071] Specific Example 4d. The compound as in Specific Example 4c, wherein R3 is Me.

[0072] Specific Example 4f. The compound as in Specific Example 4c, wherein R3 is Cl.

[0073] Specific Example 4g. The compound of Specific Example 4c, wherein R3 is F.

[0074] Specific Implementation Example 5. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R4 is H, C(=O)R19, C(=S)R19, C(=O)OR19, C(=O)SR19, S(O)2R19, C(=O)NR19R20, S(O)2NR19R20, -S(OH)2NR19R20, CH2OC(=O)OR19, CH2OC(=O)NR19R20 or CH2OC(=O)R19.

[0075] Specific Example 5a. The compound of Specific Example 5, wherein R4 is H, C(=O)R19, CO2R19, C(=O)SR19, S(O)2R19 or CH2OCOR19.

[0076] Specific Example 5b. The compound of Specific Example 5a, wherein R4 is H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tertiary butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary butyl, or COSMe.

[0077] Specific Example 5c. The compound of Specific Example 5a, wherein R4 is H, CH2OCOR19 or -S(O)2R19.

[0078] Specific Example 5d. The compound as in Specific Example 5c, wherein R4 is H, CH2OCO-tert-butyl or SO2CF3.

[0079] Specific Implementation Example 6. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R5 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl.

[0080] Specific Example 6a. The compound of Specific Example 6, wherein R5 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl or C2-C3 cyanoalkyl.

[0081] Specific Example 6b. The compound of Specific Example 6a, wherein R5 is H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C6 alkenylalkyl, C3-C6 alkynylalkyl or C2-C3 cyanoalkyl.

[0082] Specific Example 6c. The compound as in Specific Example 6b, wherein R5 is H, methyl, ethyl, propyl, cyanomethyl, CH2CCH, or cyclopropylmethyl.

[0083] Specific Example 6d. The compound as in Specific Example 6c, wherein R5 is H or methyl.

[0084] Specific Example 6e. The compound of Specific Example 6c, wherein R5 is methyl.

[0085] Specific Implementation Example 7. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R6 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl.

[0086] Specific Example 7a. The compound of Specific Example 7, wherein R6 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C7 alkenylalkyl, C3-C7 alkynylalkyl or C2-C3 cyanoalkyl.

[0087] Specific Example 7b. The compound of Specific Example 7a, wherein R6 is H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C6 alkenylalkyl, C3-C6 alkynylalkyl or C2-C3 cyanoalkyl.

[0088] Specific Example 7c. The compound of Specific Example 7b, wherein R6 is H, methyl, ethyl, propyl, cyanomethyl, CH2CCH or cyclopropylmethyl.

[0089] Specific Example 7d. The compound as in Specific Example 7c, wherein R6 is H or methyl.

[0090] Specific Example 7e. The compound of Specific Example 7e, wherein R6 is a methyl group.

[0091] Specific Implementation Example 8. As shown in the formula [1] or any of the compounds in the specific embodiments, wherein R5 and R6 together with the nitrogen atoms to which they are attached form a 3 to 7-membered ring, which contains a carbon atom and any 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2, and the ring is arbitrarily substituted with at most 5 substituents independently selected from (Rv)r, where r is the number of substituents.

[0092] Specific Example 8a. The compound of Specific Example 8, wherein the 3 to 7 member rings are 5 member rings.

[0093] Specific Example 8b. The compound of Specific Example 8a, wherein the 5-membered ring system is unsubstituted.

[0094] Specific Example 8c. The compound of Specific Example 8a, wherein the 5-membered ring system is substituted with at least one halogen, OMe, SMe or methyl.

[0095] Specific Example 8d. A compound as in any of Specific Examples 8a to 8c, wherein the 5-membered ring is pyrrolidinyl or azirzodiphenyl.

[0096] Specific Example 8e. The compound of Specific Example 8, wherein the 3 to 7 member rings are 6 member rings.

[0097] Specific Example 8f. The compound as in Specific Example 8e, wherein the 6-membered ring system is unsubstituted.

[0098] Specific Example 8g. The compound of Specific Example 8e, wherein the 6-membered ring system is substituted with at least one halogen, OMe, SMe or methyl.

[0099] Specific Example 8h. The compounds of Specific Examples 8e to 8g, wherein the 6-membered ring is α-linyl, thio-α-linyl, piperidinyl, or piperidine.

[0100] Specific Example 8i. The compound of Specific Example 8, wherein the 3 to 7 member rings are 4 member rings.

[0101] Specific Example 8j. The compound of Specific Example 8i, wherein the 4-membered ring system is unsubstituted.

[0102] Specific Example 8k. The compound of Specific Example 8i, wherein the four-membered ring system is substituted with at least one halogen, OMe, SMe or methyl.

[0103] Specific Example 81. A compound as described in any of Specific Examples 8i to 8k, wherein the 4-membered ring is an acrylamide.

[0104] Specific Example 8m. The compound of Specific Example 8, wherein the 3 to 7 member rings are 7-membered rings.

[0105] Specific Example 8n. The compound of Specific Example 8m, wherein the 7-membered ring system is unsubstituted.

[0106] Specific Example 8o. The compound of Specific Example 8m, wherein the 7-membered ring system is substituted with at least one halogen, OMe, SMe or methyl.

[0107] Specific Example 8p. Compounds of any of Specific Examples 8m to 8o, wherein the 7-membered ring is aziridine or 1,4-oxazepanyl.

[0108] Specific Implementation Example 9. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein Rv is independently selected from the group consisting of: H, halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy.

[0109] Specific Example 9a. The compound of Specific Example 9, wherein Rv is independently selected from the group consisting of: H, halogen, methyl, ethyl, propyl, cyclopropylmethyl, propargyl, OMe or cyano.

[0110] Specific Example 9b. The compound of Specific Example 9a, wherein Rv is methyl.

[0111] Specific Example 9b1. The compound of Specific Example 9a, wherein Rv is OMe.

[0112] Specific Example 9b2. The compound of Specific Example 9a, wherein Rv is H.

[0113] Specific embodiment 9c. As shown in the formula [1] or any of the compounds in the aforementioned specific embodiments 1 to 8p, wherein the two Rv are attached to the same carbon atom or to two adjacent carbon atoms, the two Rv together with the attached carbon atoms or carbon atoms form a 3 to 7-membered ring containing a carbon atom and any 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2, the ring is unsubstituted or substituted with at least one independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy.

[0114] Specific Example 9d. The compound of Specific Example 9c, wherein the two Rv systems are attached to the same carbon atom, and the two Rv systems together with the attached carbon atom form a 3 to 7-membered ring.

[0115] Specific Example 9e. The compound of Specific Example 9d, wherein the 3 to 7 members are 5-membered rings.

[0116] Specific Example 9f. The compound of Specific Example 9e, wherein the 5-membered ring is 1,3-dioxolane or cyclopentyl.

[0117] Specific Example 9g. The compound of Specific Example 9d, wherein the 3 to 7 member rings are 6-membered rings.

[0118] Specific Example 9h. The compound of Specific Example 9g, wherein the 6-membered ring is 1,3-dialkyl or cyclohexyl.

[0119] Specific Example 9i. The compound of Specific Example 9c, wherein the two Rv systems are attached to two adjacent carbon atoms, and the two Rv systems together with the attached carbon atoms form a 3 to 7-membered ring.

[0120] Specific Example 9j. The compound of Specific Example 9i, wherein the 3 to 7 members are 5-membered rings.

[0121] Specific Example 9k. The compound of Specific Example 9j, wherein the 5-membered ring is 1,3-dioxolanecycloyl or cyclopentyl.

[0122] Specific Example 91. The compound of Specific Example 9i, wherein the 3 to 7 member rings are 6 member rings.

[0123] Specific Example 9m. The compound of Specific Example 9l, wherein the 6-membered ring is 1,3-dialkyl or cyclohexyl.

[0124] Specific Implementation Example 10. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R7 is H, C1-C7 alkyl, halogen, -CN, C1-C7 haloalkyl or C1-C7 alkoxy.

[0125] Specific Example 10a. The compound of Specific Example 10, wherein R7 is H, methyl, F or Cl.

[0126] Specific Example 10b. The compound of Specific Example 10a, wherein R7 is H.

[0127] Specific Implementation Example 11. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R8 is H or C1-C7 alkyl.

[0128] Specific Example 11a. The compound of Specific Example 11, wherein R8 is H or Me.

[0129] Specific Example 11b. The compound as in Specific Example 11a, wherein R8 is H.

[0130] Specific Implementation Example 12. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R7 and R8 together form a 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members.

[0131] Specific Example 12a. The compound of Specific Example 12, wherein the 3 to 7 member rings are 5 member rings.

[0132] Specific Example 12b. The compound of Specific Example 12, wherein the 3 to 7 member rings are 6 member rings.

[0133] Specific embodiment 13. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R9 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl.

[0134] Specific Example 13a. The compound of Specific Example 13, wherein R9 is H, C1-C7 alkyl, C1-C7 haloalkyl or C2-C7 alkoxyalkyl.

[0135] Specific Example 13b. The compound of Specific Example 13a, wherein R9 is methyl, ethyl, tributyl, chloromethyl or methoxymethyl.

[0136] Specific Implementation Example 15. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R7 and R9 together form a fused 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atom members, the ring being unsubstituted or substituted with at least one independent substituent selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy.

[0137] Specific Example 15a. The compound of Specific Example 15, wherein the 3 to 7 member rings are 5 or 6 member rings.

[0138] Specific Example 15b. The compound of Specific Example 15a, wherein the 5-membered ring is cyclopentyl.

[0139] Specific Example 15c. The compound of Specific Example 15, wherein the 3 to 7 member rings are 6 member rings.

[0140] Specific Example 15d. The compound as in Specific Example 15c, wherein the 6-membered ring is cyclohexyl or tetrahydropiperan.

[0141] Specific Example 15e. A compound as in any of Specific Examples 15 to 15d, wherein the ring is unsubstituted or substituted with at least one substituent independently selected from H, halogen or C1-C4 alkyl.

[0142] Specific Example 15f. The compound as in Specific Example 15e, wherein the ring system is unsubstituted.

[0143] Specific Implementation Example 16. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R10 is H or C1-C7 alkyl.

[0144] Specific Example 16a. The compound of Specific Example 16, wherein R10 is methyl or ethyl.

[0145] Specific Example 16b. The compound of Specific Example 16, wherein R10 is H.

[0146] Specific Implementation Example 17. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R9 and R10 together with the attached carbon atoms form a 3 to 7-membered ring, which contains a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2, and the ring is arbitrarily substituted with at most 5 substituents independently selected from (Rv)r, where r is the number of substituents; or When two Rvs are attached to the same carbon atom or to two adjacent carbon atoms, the two Rvs and the attached carbon atoms or groups of carbon atoms can form a 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2.

[0147] Specific Example 17a. The compound of Specific Example 17, wherein the 3 to 7 member rings are 5 or 6 member rings.

[0148] Specific Example 17b. The compound of Specific Example 17a, wherein the 5-membered ring is cyclopentane.

[0149] Specific Example 17c. The compound of Specific Example 17, wherein the 3 to 7 member rings are 6 member rings.

[0150] Specific Example 17d. The compound as in Specific Example 17c, wherein the 6-membered ring is cyclohexane, tetrahydro-2H-piperanone, or tetrahydro-2H-thiopiperanone.

[0151] Specific Example 17e. The compound of Specific Example 17d, wherein the 6-membered ring is cyclohexane.

[0152] Specific Example 17f. The compound of Specific Example 17, wherein the 3 to 7 member rings are 4 member rings.

[0153] Specific Example 17f. The compound of Specific Example 17, wherein the 3 to 7 member rings are 7-membered rings.

[0154] Specific Implementation Example 18. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein Q is O, S, CR11R12 or NR13.

[0155] Specific Example 18a. The compound of Specific Example 18, wherein Q is O or S.

[0156] Specific Example 18b. The compound of Specific Example 18, wherein Q is O.

[0157] Specific Example 18c. The compound of Specific Example 18, wherein Q is CR11R12.

[0158] Specific Example 18d. The compound of Specific Example 18, wherein Q is NR13.

[0159] Specific Example 18e. The compound of Specific Example 18, wherein Q is O, S or CR11R12.

[0160] Specific Example 18f. The compound of Specific Example 18, wherein Q is other than NR13.

[0161] Specific Implementation Example 19. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R11 and R12 together with the attached carbon atom form a fused 3 to 7-membered ring, which contains a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, the ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy.

[0162] Specific Example 19a. The compound of Specific Example 19, wherein the 3 to 7 member rings are 5 member rings.

[0163] Specific Example 19b. The compound of Specific Example 19a, wherein the 5-membered ring is cyclopentane.

[0164] Specific Example 19c. The compound of Specific Example 19, wherein the 3 to 7 member rings are 6 member rings.

[0165] Specific Example 19d. The compound as in Specific Example 19c, wherein the 6-membered ring is cyclohexane.

[0166] Specific Example 19e. The compound of Specific Example 19, wherein the ring is an unsubstituted 5- or 6-membered ring.

[0167] Specific embodiment 20. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein r is 0, 1, 2 or 3.

[0168] Specific Example 20a. The compound of Specific Example 20, wherein r is 0.

[0169] Specific Example 20b. The compound of Specific Example 20, wherein r is 1 or 2.

[0170] Specific Example 20c. The compound of Specific Example 20, wherein r is 2.

[0171] Specific Example 20d. The compound of Specific Example 20, wherein r is 3.

[0172] Specific Example 20e. The compound of Specific Example 20, wherein r is 1.

[0173] Specific Implementation Example 21. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R13 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl;

[0174] Specific Example 21a. The compound of Specific Example 21, wherein R13 is H or C1-C7 alkyl.

[0175] Specific Example 21b. The compound of Specific Example 21a, wherein R13 is Me or Et.

[0176] Specific Example 21c. The compound as in Specific Example 21b, wherein R13 is Me.

[0177] Specific Example 21d. The compound of Specific Example 21d, wherein R13 is Et.

[0178] Specific Implementation Example 22. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R14 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C1-C7 thioalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl.

[0179] Specific Example 22a. The compound of Specific Example 22, wherein R14 is H, C1-C4 alkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C4 haloalkyl, C1-C4 haloalkyl or C1-C7 alkoxy.

[0180] Specific Example 22b. The compound as in Specific Example 22a, wherein R14 is a C1-C4 alkyl group.

[0181] Specific Example 22c. The compound as in Specific Example 22b, wherein R14 is Me.

[0182] Specific Example 22d. The compound as in Specific Example 22b, wherein R14 is Et.

[0183] Specific Example 22e. The compound as in Specific Example 22b, wherein R14 is CH2CF3.

[0184] Specific embodiment 23. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R15 is H, C1-C7 alkyl, halogen, C1-C7 haloalkyl or C1-C7 alkoxy.

[0185] Specific Example 23a. The compound of Specific Example 23, wherein R15 is H, C1-C3 alkyl or C1-C3 alkoxy.

[0186] Specific Example 23b. The compound of Specific Example 23a, wherein R15 is H or OMe.

[0187] Specific Example 23c. The compound as in Specific Example 23b, wherein R15 is H.

[0188] Specific Example 23d. The compound as in Specific Example 23b, wherein R15 is OMe.

[0189] Specific Implementation Example 24. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R16 is H, cyano, C1-C7 alkyl, halogen, C1-C4 alkylthio, C1-C7 haloalkyl or C1-C7 alkoxy.

[0190] Specific Example 24a. The compound of Specific Example 24, wherein R16 is H, cyano, C1-C4 alkyl, halogen, C1-C4 alkylthio, C1-C4 haloalkyl or C1-C4 alkoxy.

[0191] Specific Example 24b. The compound as in Specific Example 24a, wherein R16 is H or a C1-C4 alkyl group.

[0192] Specific Example 24c. The compound of Specific Example 24a, wherein R16 is H, cyano, methyl, ethyl, propyl, isopropyl, halogen, SMe, CF3 or OMe.

[0193] Specific Example 24d. The compound of Specific Example 24c, wherein R16 is H, cyano, methyl, F, SMe, CF3 or OMe.

[0194] Specific Implementation Example 25. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R17 is H, C1-C7 alkyl, halogen, -CN, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl or C2-C7 haloalkoxyalkyl.

[0195] Specific Example 25a. The compound of Specific Example 25, wherein R17 is H, C1-C4 alkyl, halogen or C1-C4 alkoxy.

[0196] Specific Example 25b. The compound of Specific Example 25a, wherein R17 is H, methyl, Cl or OMe.

[0197] Specific Implementation Example 26. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R18 is H, C1-C7 alkyl, halogen, C1-C7 haloalkyl or C1-C7 alkoxy;

[0198] Specific Example 26a. The compound of Specific Example 26, wherein R18 is H or C1-C3 alkoxy;

[0199] Specific Example 26b. The compound of Specific Example 26, wherein R18 is H, methyl or OMe.

[0200] Specific Example 26c. The compound as in Specific Example 26b, wherein R18 is H.

[0201] Specific Example 26d. The compound as in Specific Example 26b, wherein R18 is OMe.

[0202] Specific Implementation Example 27. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein R19 is C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl.

[0203] Specific Example 27a. The compound of Specific Example 27, wherein R19 is a C1-C7 alkyl or a C1-C7 haloalkyl.

[0204] Specific Example 27b. The compound of Specific Example 27a, wherein R19 is a C1-C7 alkyl group.

[0205] Specific Example 27c. The compound of Specific Example 27b, wherein R19 is methyl, ethyl, isopropyl, tert-butyl, n-butyl, tert-butyl, isobutyl, cyclopentyl, or cyclohexyl.

[0206] Specific Example 27d. The compound as in Specific Example 27c, wherein R19 is a tertiary butyl.

[0207] Specific Example 27e. The compound of Specific Example 27a, wherein R19 is a C1-C3 haloalkyl group.

[0208] Specific Example 27f. The compound as in Specific Example 27e, wherein R19 is CF3.

[0209] Specific Implementation Example 28. As shown in the formula [1] or any of the compounds in the foregoing specific embodiments, wherein Rf is a C1-C7 alkyl or a C1-C7 haloalkyl.

[0210] Specific Example 28a. The compound of Specific Example 28, wherein Rf is a C1-C3 haloalkyl group.

[0211] Specific Example 28b. The compound as in Specific Example 28a, wherein Rf is CF3.

[0212] The specific embodiments of the present invention, including the above-described specific embodiments 1 to 28b and any other specific embodiments described herein, can be combined in any manner, and the descriptions of variations in the specific embodiments are not limited to formulas. [1] Compounds, and also suitable for preparation of compounds [1] Starting compounds and intermediate compounds. Furthermore, specific embodiments of the present invention, including the above-described specific embodiments 1 to 28b and any other specific embodiments described herein, and any combination thereof, relate to the composition and methods of the present invention.

[0213] The specific combinations of embodiments 1 to 28b are described below:

[0214] Specific embodiment PA. As described in the invention summary. [1] A compound in which Q is O, S or CR11R12.

[0215] Specific embodiment A. As described in the invention summary. [1] compounds, in which G is CONR5R6; R1 is H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C1-C7 haloalkyl; R2 is H, C1-C7 alkyl, C3-C6 cycloalkyl, halogen, or CN; R3 is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R4 can be H, C(=O)R19, CO2R19, C(=O)SR19, S(O)2R19, or CH2OCOR19; R5 is H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C6 alkenylalkyl, C3-C6 alkynylalkyl, or C2-C3 cyanoalkyl; R6 is H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 ynyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C3-C6 alkenylalkyl, C3-C6 ynylalkyl, or C2-C3 cyanoalkyl; and Rf is a C1-C3 haloalkyl group.

[0216] Specific Example B. The compound as in Specific Example A, wherein... R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; R5 can be H, methyl, ethyl, propyl, cyanomethyl, CH2CCH, or cyclopropylmethyl; R6 is H, methyl, ethyl, propyl, cyanomethyl, CH2CCH, or cyclopropylmethyl; and Rf is CF3.

[0217] Specific Example C. The compound as in Specific Example B, wherein... R1 is either Me or Cl; R3 is Me; R4 is H, CH2OCO-tert-butyl, or SO2CF3; R5 is methyl; R6 is a methyl group.

[0218] Specific embodiment D. As described in the invention summary. [1] compounds, in which Q is CONR5R6; R1 is H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C1-C7 haloalkyl; R2 is H, C1-C7 alkyl, C3-C6 cycloalkyl, halogen, or CN; R3 is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R4 can be H, C(=O)R19, CO2R19, C(=O)SR19, S(O)2R19, or CH2OCOR19; R5 and R6, together with the nitrogen atoms attached thereto, form a 3 to 7-membered ring containing a carbon atom and arbitrarily 1 to 3 oxygen, sulfur, or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O), or S(O)2. The ring is arbitrarily substituted with at most 5 substituents independently selected from (Rv)r, where r is the number of substituents. Rv is independently selected from the group consisting of: H, methyl, ethyl, propyl, cyclopropylmethyl, propyne, or cyanomethyl; and r is 1 or 2.

[0219] Specific Example E. The compound as in Specific Example D, wherein... R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; R5 and R6, together with the nitrogen atoms attached to them, form 3 to 7-membered rings, of which 5-membered rings are formed; and Rf is CF3.

[0220] Specific embodiment F. The compound as in specific embodiment D, wherein... R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; R5 and R6, together with the nitrogen atoms to which they are attached, form 3 to 7-membered rings, of which 6-membered rings are formed; and Rf is CF3.

[0221] Specific embodiment A1. As described in the invention summary. [1] compounds, in which G is G-1; R1 is H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C1-C7 haloalkyl; R2 is H, C1-C7 alkyl, C3-C6 cycloalkyl, halogen, or CN; R3 is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy, or C1-C7 haloalkyl; R4 can be H, C(=O)R19, CO2R19, C(=O)SR19, S(O)2R19, or CH2OCOR19; Rf is a C1-C3 haloalkyl group.

[0222] Specific Example B1. The compound as in Specific Example A1, wherein... R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; R7 is H, C1-C7 alkyl, halogen, -CN, C1-C7 haloalkyl, or C1-C7 alkoxy; R8 is H or a C1-C7 alkyl group; R9 is H, C1-C7 alkyl, C1-C7 haloalkyl, or C2-C7 alkoxyalkyl; R10 is H or a C1-C7 alkyl group; and Rf is CF3.

[0223] Specific embodiment C1. The compound as in specific embodiment B1, wherein... R1 is either Me or Cl; R3 is Me; R4 is H, CH2OCO-tert-butyl, or SO2CF3; R7 is H; R8 is H; R9 is methyl, ethyl, tributyl, chloromethyl, or methoxymethyl; and R10 is methyl or ethyl.

[0224] Specific Example D1. The compound as in Specific Example A1, wherein... R7 and R9 together form a fused 3 to 7-membered ring containing a carbon atom and any one or two oxygen, sulfur, or nitrogen atoms. The ring is unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy. R8 is H; and R10 is H;

[0225] Specific Example E1. The compound as in Specific Example D1, wherein... R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; R7 and R9 together form fused 3 to 7-membered rings, which are 5 or 6-membered rings.

[0226] Specific Example F1. The compound as in Specific Example E1, wherein... R7 together with R9 forms a 5- or 6-membered ring of cyclopentyl, cyclohexyl, or tetrahydropiperan, which is unsubstituted or substituted with at least one substituent independently selected from the following: H, halogen, or C1-C4 alkyl.

[0227] Specific embodiment G1. The compound as in specific embodiment A1, wherein... R9 and R10, together with their attached carbon atoms, form 3 to 7-membered rings, containing carbon atoms and any 1 to 2 oxygen, sulfur, or nitrogen atoms as ring members. At most two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O), or S(O)2. The ring is arbitrarily substituted with at most 5 substituents independently selected from (Rv)r, where r is the number of substituents; or When two Rvs are attached to the same carbon atom or to two adjacent carbon atoms, the two Rvs and the attached carbon atoms or groups of carbon atoms can form a 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2. R7 is H; and R8 is H;

[0228] Specific embodiment H1. The compound as in specific embodiment G1, wherein... R1 is H, C1-C3 alkyl, halogen, or C3-C4 cycloalkyl. R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; R9 and R10, together with the carbon atoms to which they are attached, form 3 to 7-membered rings, which are 5 or 6-membered rings. Rv is independently selected from the group consisting of: H, methyl, ethyl, propyl, cyclopropylmethyl, propyne, or cyanomethyl. r is 1 or 2.

[0229] Specific Example I1. The compound as in Specific Example H1, wherein... R9 and R10 together with the attached carbon atoms form 3 to 7-membered rings, which are 5- or 6-membered rings of cyclopentane, cyclohexane, tetrahydro-2H-piperanone, or tetrahydro-2H-thiopiperanone.

[0230] Specific embodiment A2. As described in the invention summary. [1] compounds, in which G is G-2; R1 is H, C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, or C1-C7 haloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; and Rf is a C1-C3 haloalkyl group.

[0231] Specific Example B2. The compound as in Specific Example A2, wherein... Q is either O or S; R7 is H; R8 is H; Rf is CF3. R9 and R10, together with the carbon atoms to which they are attached, form 3 to 7-membered rings, which are 5 or 6-membered rings; Rv is independently selected from the group consisting of: H, methyl, ethyl, propyl, cyclopropylmethyl, propyne, or cyanomethyl. r is 1 or 2.

[0232] Specific embodiment C2. The compound as in specific embodiment B2, wherein... R9 and R10, together with the attached carbon atoms, form cyclopentane, cyclohexane, tetrahydro-2H-piperanane, or tetrahydro-2H-thiopiperanane; and Rv is H.

[0233] Specific Example D2. The compound as in Specific Example A2, wherein... Q is CR11R12; R7 is H; R8 is H; R9 is H; R10 is H; R11 and R12, together with their attached carbon atoms, form fused 3- to 7-membered rings containing a carbon atom and any one or two oxygen, sulfur, or nitrogen atoms as ring members. The ring is unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; and Rf is CF3.

[0234] Specific Example E2. The compound as in Specific Example D2, wherein... R11 and R12 together with the attached carbon atoms form fused 3 to 7-membered rings, which are unsubstituted 5 or 6-membered rings.

[0235] Specific embodiment A3. As described in the invention summary. [1] compounds, in which G is G-3; R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; R13 is a C1-C7 alkyl group; R14 is a C1-C4 alkyl group; R15 is H; and Rf is a C1-C3 haloalkyl group.

[0236] Specific embodiment A4. As described in the invention summary. [1] compounds, in which G is G-4; R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; R13 is a C1-C7 alkyl group; Rf is a C1-C3 haloalkyl group; R15 is H, C1-C3 alkyl, or C1-C3 alkoxy; and R16 is H, cyano, C1-C4 alkyl, halogen, C1-C4 alkylthio, C1-C4 haloalkyl, or C1-C4 alkoxy.

[0237] Specific embodiment A5. As described in the invention summary. [1] compounds, in which G is G-5; R1 is H, C1-C7 alkyl, halogen, or C3-C7 cycloalkyl; R2 is H, Me, or F; R3 can be H, Me, F, Cl, CN, OMe, or CF3; R4 can be H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl, or COSMe; Rf is a C1-C3 haloalkyl group; R16 is H or a C1-C4 alkyl group; R17 is H, C1-C4 alkyl, halogen, or C1-C4 alkoxy; and R18 is H or C1-C3 alkoxy group.

[0238] Specific embodiments include those selected from the group consisting of the following. [1] Compound: N-[2,4-Dimethyl-5-(1-piperidinylcarbonyl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 260); N-[2-chloro-4-methyl-5-(4-pyrinylcarbonyl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 16); N-[2,4-Dimethyl-5-(4-pyrinylcarbonyl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 6); N-[2-chloro-4-methyl-5-(1-piperidinylcarbonyl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 18); 3-Fluoro-N,N,2,4-Tetramethyl-5-[[(trifluoromethyl)sulfonyl]amino]benzamide (Compound 128); 1,1,1-Trifluoro-N-[3-fluoro-2,4-dimethyl-5-(4-oxolinylcarbonyl)phenyl]methanesulfonamide (compound 190); N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 207); N-[2,4-Dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopentane[d]isoazol-3-yl]phenyl]-1,1,1-trifluoromethanesulfonamide (compound 103); N-[2,4-Dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 197); N-[2,4-Dimethyl-5-(3a,4,7,7a-tetrahydro-5H-piperanyl[4,3-d]isoazol-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 121); N-[2,4-Dimethyl-5-(3a,6,7,7a-tetrahydro-4H-piperanyl[3,4-d]isoazol-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 120); N-[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4,5]dec-2-yl)phenyl]-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (compound 267); 2,2-Dimethylpropionic acid [[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (compound 140); 2,2-Dimethylpropionic acid [[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (compound 159); 2,2-Dimethylpropionic acid [[2,4-dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopentane[d]isoazol-3-yl]phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (compound 100); 2,2-Dimethylpropionic acid [[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4.5]dec-2-yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (compound 268);

[0239] Other specific embodiments include those selected from the group consisting of the following. [1] Compound: Specific embodiments include those selected from the group consisting of the following. [1] Compound: 2,2-Dimethylpropionic acid [[(trifluoromethyl)sulfonyl][2,3,4-trimethyl-5-(4-hydroxylinylcarbonyl)phenyl]amino]methyl ester (compound 324); Ethyl N-[(trifluoromethyl)sulfonyl]-N-[2,3,4-trimethyl-5-(1-piperidinylcarbonyl)phenyl]carbamate (compound 330); 2,2-Dimethylpropionic acid [[(trifluoromethyl)sulfonyl][2,3,4-trimethyl-5-(1-piperidinylcarbonyl)phenyl]amino]methyl ester (compound 329); 1,1,1-Trifluoro-N-[2,3,4-trimethyl-5-(4-hydroxylinylcarbonyl)phenyl]methanesulfonamide (compound 289); and 2,2-Dimethylpropionic acid [[(trifluoromethyl)sulfonyl][2,3,4-trimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopentazo-3-yl]phenyl]amino]methyl ester (compound 336); Other specific implementation examples include: [1] compounds, in which G is CONR5R6 and NR5R6 is J-3a, R1 is Me, R2 is Me, R3 is Me, R4 is CH2OCO-tertiary butyl and Rf is CF3 (compound 331); G is CONR5R6 and NR5R6 is J-4, R1 is Me, R2 is Me, R3 is Me, R4 is CO2Et and Rf is CF3 (compound 325).

[0240] This invention also relates to a method for controlling unwanted vegetation, comprising applying a herbicidally effective amount of the compound of the invention (as described herein) to the vegetation site. Specific embodiments of the method of application are noteworthy, relating to the compounds described above. The compounds of the invention are particularly suitable for selective weed control in various crops (such as wheat, barley, corn, soybean, sunflower, cotton, rapeseed, and rice) and specialty crops (such as sugarcane, citrus, fruit, and stone fruit crops).

[0241] Also noteworthy is the herbicidal composition of the present invention which includes the compounds of the above-mentioned specific embodiments.

[0242] This invention also includes a weed control mixture comprising (a) selected from the formula [1], its N-oxides and salts, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetylhydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-acetylshikimate-3-phosphate (EPSP) synthase inhibitors, and (b6) photosystem I electrophoresis. (b7) Diverter, (b8) Protoporphyrinogen oxidase (PPO) inhibitor, (b9) Glutamic acid synthase (GS) inhibitor, (b10) Very long chain fatty acid (VLCFA) elongation enzyme inhibitor, (b11) Auxin transport inhibitor, (b12) Lycopene desaturase (PDS) inhibitor, (b13) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor, (b14) Alpha-2-benzene transferase. HST enzyme inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides, including mitotic disruptors, organoarsenic agents, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, and pyributicarb, (b16) herbicide safeners, and salts of compounds (b1) to (b16).

[0243] "Photosystem II inhibitors" (b1) are compounds that bind to the D-1 protein at the QB binding site, thereby blocking electron migration from QA to QB across the thylakoid membrane of chloroplasts. Electrons blocked from crossing photosystem II undergo a series of reactions to form toxic compounds that damage the cell membrane, causing chloroplast swelling, membrane leakage, and ultimately cell destruction. The QB binding site has three distinct binding sites: site A binds triazine (e.g., atrazine), triazinone (e.g., hexazinone), and uracil (e.g., bromacil); site B binds phenylurea (e.g., diuron); and site C binds benzothiadiazole (e.g., bentazon), nitriles (e.g., bromoxynil), and phenyl-pyridazine (e.g., pyridate).Examples of photosystem II inhibitors include ametryn, amicabazone, atrazine, betazon, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, and isour The following herbicides are listed: lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, and trietazine.

[0244] "AHAS inhibitors" (b2) are compounds that inhibit acetylhydroxy acid synthase (AHAS) (also known as acetyllactic acid synthase (ALS)), and thus kill plants by inhibiting the production of branched aliphatic amino acids (such as valine, leucine and isoleucine), which are required for protein synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, and flupyrsulfuron-methyl. Flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron ron), iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-tris(2-yl)amino]carbonyl]-benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-di(3-yl)N-[[(4,(6-Dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfadiazine), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propimidazo[1,2-b]pyrazosulfuron-3-sulfadiazine), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyr... The following are listed: iminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfurosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-trisulfon-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonyl), triasulfuron, tribensulfuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl, and tritosulfuron.

[0245] "ACCase inhibitors" (b3) are compounds that inhibit acetyl-CoA carboxylase, an enzyme responsible for catalyzing early steps in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes; without them, new cells cannot be created. Inhibition of acetyl-CoA carboxylase and subsequent lipid deficiency lead to loss of cell membrane integrity, particularly in active growth areas such as meristems. Ultimately, shoots and rhizomes cease growth, and shoot meristems and rhizome shoots begin to wither. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, and cyhalofop. Sethoxydim, tepraloxydim, and tralkoxydim, including analytical forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P, and quizalofop-P, as well as ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, and fenoxaprop-P-ethyl.

[0246] Auxins are plant hormones that regulate growth in many plant tissues. "Auxin mimics" (b4) are compounds that mimic the plant growth hormone auxin, thereby causing uncontrolled and chaotic growth, leading to the death of susceptible plant species. Examples of auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters, as well as their sodium and potassium salts; aminopyralid; benzolin-ethyl; chloramben; clacyfos; cromopyr; clopyralid; dicamba; 2,4-D; 2,4-DB; dichlorprop; fluroxypyr; and haloxifen. lauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), methyl halauxifen-methyl (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid methyl ester), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, trichloropyr, and 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid methyl ester.

[0247] "EPSP synthase inhibitors" (b5) are compounds that inhibit the enzyme 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids (such as tyrosine, tryptophan, and phenylalanine). EPSP inhibitor herbicides are rapidly absorbed by plant leaves and translocated to the growing point in the phloem. Glyphosate belongs to this group of relatively non-selective post-emergence herbicides. Glyphosate includes esters and salts such as ammonium salts, isopropylammonium salts, potassium salts, sodium salts (including sesquisodium) and trimethylsulfonium (also known as sulfosate).

[0248] "Photosystem I electron diverters" (b6) are compounds that accept electrons from photosystem I and generate hydroxyl groups after several cycles. These groups are highly reactive and rapidly destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This disrupts cell membrane integrity, causing cells and organelles to "leak," leading to rapid wilting and drying of leaves, ultimately resulting in plant death. Examples of this type II photosynthesis inhibitor include diquat and paraquat.

[0249] "PPO inhibitors" (b7) are compounds that inhibit proporphyrinogen oxidase. In plants, they rapidly lead to the formation of highly reactive compounds that damage cell membranes, causing cell sap leakage. Examples of PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, and bifenox. Butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, cyclopentadiene Pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, trifludimoxazin (dihydro-1,5-dimethyl-6-thio-3-[2,2]pyrazol) ,7-trifluoro-3,4-dihydro-3-sideoxy-4-(2-propyn-1-yl)-2H-1,4-benzo[6-yl]-1,3,5-trisyl-2,4(1H,3H)-dione) and tiafenacil (N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-sideoxy-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-sideoxypropyl]-β-propanine methyl ester).

[0250] "GS inhibitors" (b8) are compounds that inhibit the activity of glutamic acid synthase, an enzyme used by plants to convert ammonia into glutamic acid. As a result, ammonia accumulates while glutamic acid levels decrease. The combined effects of ammonia toxicity and the lack of other amino acids required for metabolic processes can harm plants. GS inhibitors include glufosinate and its esters and salts, such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino-4-(hydroxymethylphosphono)butyric acid), and bilanaphos.

[0251] "VLCFA elongation enzyme inhibitor" (b9) is a herbicide with a wide variety of chemical structures that inhibits elongation enzymes. Elongation enzymes are enzymes located in or near chloroplasts that are involved in the biosynthesis of VLCFAs. In plants, very long-chain fatty acids are the main components of hydrophobic polymers, which prevent leaf surfaces from drying out and provide pollen grain stability. These herbicides include acetochlor, alachlor, anilofos, butachlor, cefenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoazole), fentrazamide, flufenacet, indanofan, mefenacet, and metazachlor. r), metolachlor, naproanilide, napropamide, metolachlor-M (napropamide-M)((2R)-N,N-diethyl-2-(1-naphthoxy)propamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including analytical forms such as S-metolachlor and chloroacetamide and oxyacetamide.

[0252] "Auxin transport inhibitors" (b10) are chemical substances that inhibit the transport of auxin in plants, such as by binding to auxin carrier proteins. Examples of auxin transport inhibitors include diflufenzopyr and naptalam (also known as N-(1-naphthyl)-o-aminobenzoic acid and 2-[(1-naphthylamino)carbonyl]benzoic acid).

[0253] "PDS inhibitors" (b11) are compounds that inhibit the phytoene desaturase step in the carotenoid biosynthesis pathway. Examples of PDS inhibitors include beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurzon, and picolinafen.

[0254] HPPD inhibitors (b12) are chemical substances that inhibit the biosynthesis of 4-hydroxyphenyl-pyruvate-dioxanose. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), and fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-sideoxy-2-quinoline]carbonyl]-1 3-Cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate (1-[[1-ethyl -4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonylurea)benzyl]-1H-pyrazol-5-yl]oxy]ethyl methyl carbonate), toramezone, 5-chloro-3-[(2-hydroxy-6-sideoxy-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoline ketone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyrazolone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-sideoxy-1-cyclohexenyl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoline ketone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyrazolone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-sideoxy-1-cyclohexenyl)carbonyl]-1H ... [[(2-hydroxy-6-sideoxy-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-tris(2,4H)-3,5(2H,4H)-dione, 5-[(2-hydroxy-6-sideoxy-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-(methylsulfinyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.

[0255] "HST inhibitors" (b13) interfere with the ability of plants to convert melanurate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby interfering with carotenoid biosynthesis. Examples of HST inhibitors include haloxydine, pyriclor, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthidin-2(1H)-one, 7-(3,5-dichloro-4-pyridyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyr-6(5H)-one, and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridone.

[0256] HST inhibitors also include formulas [A] and [B] compounds. Where Rd1 is H, Cl, or CF3; Rd2 is H, Cl, or Br; Rd3 is H or Cl; Rd4 is H, Cl, or CF3; Rd5 is CH3, CH2CH3, or CH2CHF2; and Rd6 is OH or -OC(=O)-isopropyl; and Re1 is H, F, Cl, CH3, or CH2CH3; Re2 is H or CF3; Re3 is H, CH3, or CH2CH3; Re4 is H, F, or Br; Re5 is Cl, CH3, CF3, OCF3, or CH2CH3; Re6 is H, CH3, CH2CHF2, or C≡CH; Re7 is OH, -OC(=O)Et, -OC(=O)-isopropyl, or -OC(=O)-tert-butyl; and Ae8 is N or CH.

[0257] "Cellulose biosynthesis inhibitors" (b14) inhibit cellulose biosynthesis in specific plants. They are most effective when applied to young or fast-growing plants before or early after bud break. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N 2-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-ind-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben, and triaziflam.

[0258] "Other herbicides" (b15) include herbicides that act through various modes of action, such as mitosis disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl), organoarsenic agents (e.g., DSMA and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors, and cell wall biosynthesis inhibitors. Other herbicides include herbicides with unknown modes of action or those not belonging to the specific categories listed in (b1) to (b14), or herbicides that act through a combination of the above modes of action. Other examples of herbicides include aclonifen, asulam, amitrol, bromobutide, cinmethylin, cromazine, cumyluron, cyclopyrimorate (4-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-tertyl ester), daimuron, difenzoquat, etobenzanid, and fluometuron. Herbicides include flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone (1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-sideoxy-4H-1,2,4-triazol-4-methoxyamine), metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoazole.

[0259] "Other herbicides" (b15) also includes compounds of formula (b15A). in R12′ is H, C1-C6 alkyl, C1-C6 haloalkyl, or C4-C8 cycloalkyl; R13′ is H, C1-C6 alkyl, or C1-C6 alkoxy; Q1 is an arbitrarily substituted ring system selected from the group consisting of: phenyl, thiophene, pyridinyl, benzodiazepine, naphthyl, benzofuranyl, furanyl, benzothiophenyl, and pyrazolyl, wherein when substituted, the ring system is substituted with 1 to 3 R14′. Q2 is an arbitrarily substituted ring system selected from the group consisting of: phenyl, pyridinyl, benzodiazolyl, pyridoneyl, thiadiazolyl, thiazolyl, and acezolyl, wherein when substituted, the ring system is substituted with 1 to 3 R15′. Each R14′ group is independently a halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 cycloalkyl, cyano, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, SF5, NHR17; or phenyl optionally substituted with 1 to 3 R16 groups; or pyrazolyl optionally substituted with 1 to 3 R16 groups. Each R15′ group is independently a halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, cyano, nitro, C1-C6 alkylthio, C1-C6 alkylsulfinyl, or C1-C6 alkylsulfonyl. Each R16′ group is independently halogenated, C1-C6 alkyl, or C1-C6 haloalkyl; and R17′ is a C1-C4 alkoxycarbonyl group.

[0260] In one specific embodiment, "other herbicides" (b15) also includes compounds of formula (b15A), preferably, R12′ is H or a C1-C6 alkyl group; more preferably, R12′ is H or a methyl group. Preferably, R13′ is H. Preferably, Q1 is a benzene ring or a pyridine ring, each ring being substituted by 1 to 3 R14′; more preferably, Q1 is a benzene ring substituted by 1 to 2 R14′. Preferably, Q2 is a benzene ring substituted by 1 to 3 R15′; more preferably, Q2 is a benzene ring substituted by 1 to 2 R15′. Preferably, each R14′ is independently a halogen, a C1-C4 alkyl, a C1-C3 haloalkyl, a C1-C3 alkoxy, or a C1-C3 haloalkoxy; more preferably, each R14′ is independently chlorine, fluorine, bromine, a C1-C2 haloalkyl, a C1-C2 haloalkoxy, or a C1-C2 alkoxy. Preferably, each R15′ is independently a halogen, a C1-C4 alkyl, or a C1-C3 haloalkoxy; more preferably, each R15′ is independently chlorine, fluorine, bromine, a C1-C2 haloalkyl, a C1-C2 haloalkoxy, or a C1-C2 alkoxy. Particularly preferred "other herbicides" (b15) include any one of the following (b15A-1) to (b15A-19): (b15A-1) (b15A-2) (b15A-3) (b15A-4) (b15A-5) (b15A-6) (b15A-7) (b15A-8) (b15A-9) (b15A-10) (b15A-11) (b15A-12) (b15A-13) (b15A-14) (b15A-15) (b15A-16) (b15A-17) (b15A-18) (b15A-19)

[0261] "Other herbicides" (b15) also includes compounds of formula (b15B). in R18′ is H, C1-C6 alkyl, C1-C6 haloalkyl, or C4-C8 cycloalkyl; Each R19′ group is independently a halogen, a C1-C6 haloalkyl, or a C1-C6 haloalkoxy. p is an integer of 0, 1, 2, or 3; Each R20′ group is independently a halogen, a C1-C6 haloalkyl, or a C1-C6 haloalkoxy; and q is an integer of 0, 1, 2 or 3.

[0262] In one specific embodiment, "other herbicides" (b15) also includes compounds of formula (b15B), preferably, R18 is H, methyl, ethyl, or propyl; more preferably, R18 is H or methyl; most preferably, R18 is H. Preferably, each R19 is independently chlorinated, fluorinated, C1-C3 haloalkyl, or C1-C3 haloalkoxy; more preferably, each R19 is independently chlorinated, fluorinated, C1 fluoroalkyl (i.e., fluoromethyl, difluoromethyl, or trifluoromethyl) or C1 fluoroalkoxy (i.e., trifluoromethoxy, difluoromethoxy, or fluoromethoxy). Preferably, each R20 is independently chlorinated, fluorinated, C1 haloalkyl, or C1 haloalkoxy; more preferably, each R20 is independently chlorinated, fluorinated, C1 fluoroalkyl (i.e., fluoromethyl, difluoromethyl, or trifluoromethyl) or C1 fluoroalkoxy (i.e., trifluoromethoxy, difluoromethoxy, or fluoromethoxy). The particularly preferred “other herbicides” (b15) include any one of the following (b15B-1) to (b15B-19): (b15B-1) (b15B-2) (b15B-3) (b15B-4) (b15B-5) (b15B-6) (b15B-7) (b15B-8) (b15B-9) (b15B-10) (b15B-11) (b15B-12) (b15B-13) (b15B-14) (b15B-15) (b15B-16) (b15B-17) (b15B-18) (b15B-19).

[0263] In another specific embodiment, "other herbicides" (b15) also includes compounds of formula (b15C). Where R1′ is Cl, Br or CN; and R2′ is C(=O)CH2CH2CF3, CH2CH2CH2CH2CF3 or 3-CHF2-isoazol-5-yl.

[0264] "Herbicide safeners" (b16) are substances added to herbicide formulations to eliminate or reduce the phytotoxic effects of herbicides on specific crops. These compounds protect crops from herbicide damage, but typically do not prevent herbicides from causing unwanted vegetation. Examples of herbicide safeners include, but are not limited to, benzoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, and naphthalic anhydride. anhydride), oxabetrinil, N-(aminocarbonyl)-2-toluenesulfonamide and N-(amino-carbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dichlorobenzene (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro-[4.5]decane (MON 4660), 2,2-dichloro-1-(2,2,5-trimethyl-3-azolidinyl)-acetone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzylamine.

[0265] Mode [1] The compound can be prepared by conventional methods known in the field of synthetic organic chemistry. One or more of the following methods and variations as described in Schemes 1 to 14 can be used for the preparation of the compound. [1] Compounds. Unless otherwise stated, the following formulas are... [1] to

[15] The definitions of G, R1 to R19, Rv, and Rf in the compound are as defined in the above-described invention. [1a]、 [1b]、 [3a]、 [3b]、 [3b′]、 [3c]、 [3d]、 [3e] and [3f] The compound is of formula [ ] [1] and [3] Various subsets of compounds; and formulas [1a]、 [1b]、 [3a]、 [3b]、 [3b′]、 [3c]、 [3d]、 [3e] and All substituent systems of [3f] are as described above for the formula. [1] is defined as follows, unless otherwise stated in this invention, including all embodiments.

[0266] As shown in Scheme 1, the formula [1a] Compound (i.e., formula one) [1] The preparation of the compound, wherein R4 is H, can be carried out by, at a temperature typically ranging from -78°C to 0°C, in the presence of a suitable base (such as pyridine, triethylamine, diisopropylethylamine, or potassium carbonate), in a compatible solvent (including but not limited to tetrahydrofuran, acetonitrile, toluene, diethyl ether, dimethyl ether, dichloromethane, or N,N-dimethylformamide), by appropriately substituted compound of the formula [2] It is obtained by reacting aniline with 1 equivalent (or slightly more than 1 equivalent) of RfSO2Cl compound or the corresponding Rf(SO2)2O anhydride. Or, formula [1] [b]Compound (i.e., formula one) [1] The compound, wherein R4 is SO2, R19 and R19 are Rf) is formed by reacting the compound under similar reaction conditions as described above. [2] It is obtained by reacting aniline with 2 equivalents (or slightly more than 2.0 equivalents) of a compound of formula RfSO2Cl or a corresponding anhydride of formula Rf(SO2)2O. The mixture is then treated with an excess of alkaline aqueous solution. [1b] Disulfonamide, subsequently neutralized or acidified, will readily provide the corresponding formula. [1a] Monosulfonamide. The preferred conditions for this hydrolysis are usually an aqueous solution of sodium hydroxide or potassium hydroxide, with an optional cosolvent such as methanol, ethanol, dialkyl or tetrahydrofuran, followed by neutralization or acidification with concentrated hydrochloric acid or an aqueous solution of hydrochloric acid. Option 1

[0267] As shown in Scheme 2, under catalytic hydrogenation conditions of 5-10% palladium metal on carbon or platinum oxide in solvents including but not limited to hydrogen environments (such as methanol, ethanol, or ethyl acetate), it is easily achieved by formula [3] Hydrogenation of nitrobenzene to obtain formula [2] Substituted aniline. This reaction can usually be carried out in a Parr Hydrogenator. Alternatively, the reduction of the nitro group can be carried out in the presence of NiCl2·6H2O with acetic acid containing activated zinc metal, aqueous hydrochloric acid containing stannous chloride, aqueous acetic acid or alcohol containing iron metal, or an aqueous ethyl acetate solution with ammonium chloride (e.g., Fe in an aqueous ethanol solution with 3 equivalents of ammonium chloride), or with methanol containing sodium borohydride (see Journal the American Chemical Society, Vol. 127, p. 119 (2005)). Option 2

[0268] As shown in Scheme 3, the formula [3] [a] Nitrobenzene substituted with amide (i.e., formula 1) [3] compounds, where G is CONR5R6) can be derived from formula [3] [4] Prepared by substituted nitrobenzene carboxylic acid, which is prepared by initially forming an acid chloride, followed by reacting it with an amine of formula HNR5R6. Alternatively, formula HNR5R6... [3a] The compound can be produced by directly using an anhydride amide coupling agent (arbitrarily with a base in a suitable solvent) to form the compound of formula [3a]. [4] It is prepared by reacting a carboxylic acid with an amine of formula HNR5R6. The reaction can be carried out in a suitable solvent (such as dichloromethane, toluene, or dichloroethane) containing oxalichloromethyl chloride or thionyl chloride and a catalytic amount of N,N-dimethylformamide. [4] An acid chloride is obtained. The resulting acid chloride reacts with an amine of formula HNR5R6 in the presence of a solvent containing triethylamine, diisopropylethylamine (Hunig's base) or pyridine (such as tetrahydrofuran, dimethyl ether, or dichloromethane). This reaction is suitable for the direct coupling of carboxylic acids. [4] Dehydrating amide coupling agents with amine HNR5R6 include N,N′-dicyclohexylcarbodiimide (DCC), (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent), propanephosphonic anhydride (T3P reagent), or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). Typically, a base (such as triethylamine, diisopropylethylamine, pyridine, or N,N-dimethylaminopyridine (DMAP)) is added to this dehydration coupling reaction in the presence of a solvent (such as N,N-dimethylformamide, acetonitrile, or dichloromethane). The reaction temperature is generally in the range of 0°C to ambient temperature. Option 3

[0269] As shown in Scheme 4, the formula [3b] Isozoline-substituted nitrobenzene intermediates (i.e., formula I) [3] The compound, wherein G is an isozolidine ring, can be prepared by reacting the compound in a compatible solvent (such as chloroform, dichloromethane, acetonitrile, tetrahydrofuran, toluene, dimethyl ether or dichloroethane) in the presence of a suitable base (triethylamine, diisopropylethylamine or pyridine) at a temperature of 0°C to ambient temperature. [5] Nitrophenylchlorooxime is prepared by a cycloaddition reaction with an alkene of formula R7R8C=CR9R10. When an unsymmetric alkene R7R8C=CR9R10 is used in this cycloaddition reaction, the following formula can be obtained: [3b] and [3b′] A mixture of regioisozoline nitrobenzene isomers, in which the two regioisoomers may need to be separated by silicone chromatography. Option 4

[0270] Mode [5] Chlorooxime can be produced by means of a solvent containing N-chlorosuccinimide, sodium hypochlorite, or chlorine (such as N,N-dimethylformamide, acetonitrile, dichloromethane, dichloroethane, or toluene) in a temperature generally including, but not limited to, at a temperature of 0°C to ambient temperature. [6] The oxime is prepared by chlorination reaction with a chlorinating agent, as shown in Scheme 5. Option 5

[0271] Mode [6] Oxime can be derived from the formula [7] Nitrobenzaldehyde is obtained by reacting a hydroxylamine (as a free base or a hydrochloride or acetate) with a base (such as sodium acetate, pyridine or potassium carbonate) in a compatible solvent (including but not limited to methanol, ethanol, acetonitrile, dichloromethane) in a temperature range of 0°C to ambient temperature, as shown in Scheme 6. Option 6

[0272] Mode [7] The compound can be prepared by reacting it in a suitable solvent (including but not limited to dichloromethane or dichloroethane) with a suitable oxidizing agent (such as pyridinium chlorochromate (PCC, optionally combined with Celite® diatomaceous earth filter aid), chromic acid or manganese oxide (IV). [8] It is prepared by oxidation of nitrobenzyl alcohol, as shown in Scheme 7. Alternatively, the oxidation reaction can be carried out under Swern conditions using oxalic acid chloride, dimethyl sulfoxide, and triethylamine. The oxidation of benzyl alcohol to benzaldehyde is well documented in organic synthetic chemistry. Option 7

[0273] Mode [8] Nitrobenzyl alcohol can be obtained from formula [4] Nitrobenzoic acid is obtained by reduction reaction of tetrahydrofuran, diethyl ether or dialkyl containing 2-3 equivalents of borane (such as BH3·THF) or lithium aluminum hydride at a temperature typically ranging from -78°C to ambient temperature, as shown in Scheme 8. Option 8

[0274] Mode [9] Benzoic acid can be nitrated in a mixture of nitric acid and sulfuric acid at temperatures ranging from 0°C to ambient temperature to obtain the product of formula […]. [4] Nitrobenzoic acid, as shown in Scheme 9. Other nitronium ion sources for this nitration (including nitronium tetrafluoroborate, acetyl nitrate, and guanidine nitrate) can also be used in suitable solvents (such as tetramethylene sulfonate) to complete this reaction. [9] Benzoic acid is readily available commercially or readily prepared by methods established in the literature. Option 9

[0275] As shown in Scheme 10, the formula [3c] Compound (i.e., formula one) [3] compounds, where G is G-2) can be obtained by formula [10a] Nitrobenzenes substituted with m-bromo or m-iodine (i.e., formula 1)

[10] of the compounds, wherein X is bromine or iodine) and the formula

[11] Copper-mediated coupling of cyclic carbamates, cyclic thiocarbamates, cyclic cycloamines, or cyclic ureas (where Q is O, S, CR11R12, or NR13) is prepared by copper-mediated coupling in the presence of copper iodide (I) and a diamine ligand (such as trans-N,N'-dimethylcyclohexane-1,2-diamine or tetramethylethylenediamine (TMEDA)) and potassium phosphate (K3PO4) in a suitable solvent (such as N,N-dimethylformamide, acetonitrile, tetrahydrofuran, or dimethylformamide), with water as an optional co-solvent. Similar copper-mediated coupling can also be carried out under Chan-Lam conditions, where the formula is... [10b] Boric acid (i.e., formula one) [1] [0] compounds, wherein X is B(OH)2) in dichloromethane in the presence of copper acetate(II) and pyridine, and the compound of formula [1] [1] Compound coupling. This cross-coupling can also be achieved using the detailed Buchwald-Hartwig amination scheme. [10a] and formula [1] [1] The reaction involves a palladium-mediated reaction with a suitable phosphine ligand in a suitable solvent (such as tetrahydrofuran, toluene, or dichloromethane) as part of a precatalyst or as an additive. For most matrices, an auxiliary base is used, such as sodium terbutoxide or cesium carbonate in the reaction. Examples of palladium catalysts suitable for this conversion include, but are not limited to, tetra(triphenylphosphine)palladium(O)[Pd(PPh3)4], bis(triphenylphosphine)palladium chloride[PdCl2(PPh3)2], palladium(II) chloride tri(2-methylphenyl)phosphine[PdCl2[P(o-Tol)3]2] or [1,1′bis(diphenylphosphine)ferronyl]dichloropalladium(II)[Pd(dppf)Cl2]. Finally, this cross-coupling can also be accomplished with palladium acetate [Pd(OAc)2] or tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3], which is used in combination with a suitable dialkyl diarylphosphine ligand containing toluene or cesium carbonate and a base (such as sodium tributoxide).

[0276] Mode [10b] Nitrophenylboronic acid can also be prepared by Suzuki coupling reaction. Option 10

[0277] Uracil Substitution Formula [3] [d] Nitrobenzene (i.e., formula 1) [3] compounds, wherein G is G-3) and substituted with terpinene [3e] Nitrobenzene (i.e., formula 1) [3] compounds, where G is G-4) can be obtained by formula

[12] Pinacol nitrobenzeneboronic acid ester with appropriately substituted 5-bromine or 5-iodine substituted formula

[13] Uracil (where X is bromine or iodine) or formula

[14] It is prepared by cross-coupling of pyrazine (where X is bromine or iodine) in a suitable solvent (such as aqueous dialkyl, aqueous tetrahydrofuran or N,N-dimethylformamide) with a suitable base (such as sodium carbonate, potassium carbonate or sodium bicarbonate), as outlined in Scheme 11. Examples of palladium catalysts suitable for this conversion include, but are not limited to, tetra(triphenylphosphine)palladium(O)[Pd(PPh3)4] or bis(triphenylphosphine)palladium chloride[PdCl2(PPh3)2].

[0278] By means of established methods,

[13] Halogenated uracil (where X is bromine or iodine) can be readily obtained by formula [13a] It is prepared by halogenation of uracil (where X is hydrogen) with bromine, iodine, N-bromosuccinimide, or N-iodosuccinimide in a suitable solvent (such as acetic acid, dichloromethane, carbon tetrachloride, chloroform, acetonitrile, or N,N-dimethylformamide).

[14] pyridone (where X is iodine) can be derived from formula [14a] Dalte-1, which is prepared by treating 2,2,6,6-tetramethylpiperidinyl zinc chloride-LiCl (TMPZnCl·LiCl) in tetrahydrofuran or dialkyl, followed by the addition of iodine. Option 11

[0279] Mode

[12] Pinalol nitrobenzeneboronic acid ester can be readily derived from formula

[15] Nitrobenzyl bromide or iodine is prepared by treatment with bis(pinacolato)diboron (B2pin2) in the presence of a solvent containing a palladium catalyst (such as bis(triphenylphosphine)palladium chloride [PdCl2(PPh3)2]) (i.e., dialkyl or tetrahydrofuran), as shown in Scheme 12. Option 12

[0280] As shown in Scheme 13, the formula [3] [f] N-linked terephthalone nitrobenzene (i.e., formula 1) [3] compounds, where G is G-5) can be obtained by formula [10a] Bromine- or iodine-substituted nitrobenzene (where X is bromine or iodine) and formula

[15] Dalteone is prepared by cross-coupling in the presence of copper iodide (I) and K3PO4 with a diamine ligand (i.e., trans-N,N′-dimethylcyclohexane-1,2-diamine or tetramethylethylenediamine (TMEDA)) in a suitable solvent (N,N-dimethylformamide, acetonitrile, tetrahydrofuran or dimethylethane), with water as the co-solvent, in any case. Alternatively, a similar coupling can be performed by atomizing the formula under Buchwald-Hartwig amination conditions. [10b] Arylboronic acid (where X is B(OH)2 and the formula)

[15] Cross-coupling. Option 13

[0281] As shown in Scheme 14, the formula [1] A compound (where R4 is C(=O)R19, C(=S)R19, CO2R9, C(=O)SR19, S(O)2R19, CONR20R19, S(O)2NR20R19, S(OH)2NR20R19 or CH2OCOR19) can be obtained by incorporating the compound of the formula into a solvent (including but not limited to tetrahydrofuran, dimethyl ether, dichloromethane, acetonitrile or N,N-dimethylformamide) in the presence of a base (such as triethylamine, pyridine or diisopropylethylamine (Hounig base) or potassium carbonate). [1] It is prepared by reacting sulfaniline (where R4 is hydrogen) with a suitably substituted amide halide, thioamide halide, aminomethyl amide halide, sulfanilide or aminosulfanilide or amide methyl halide (i.e. ClCH2O(C=O)R19). Option 14

[0282] It should be recognized that some of the reagents and reaction conditions described above for the preparation of compounds of formula 1 may not be compatible with the functionality present in certain intermediates. In such cases, incorporating the interconversion of protecting / deprotecting sequences or functional groups into the synthesis will help to obtain the desired product. The use and selection of protecting groups will be obvious to those with ordinary knowledge of chemical synthesis (see, for example, Greene, TW; Wuts, PGM Protective Groups in Organic Synthesis, 2nd Ed.; Wiley: New York, 1991). Those with ordinary knowledge in the art will recognize that in some cases, after the introduction of a given reagent (as described in any individual scheme), additional conventional synthetic steps, not detailed here, may be necessary to complete the product of formula 1. [1] Synthesis of compounds. Those skilled in the art will also recognize that it may be necessary to perform the combination of steps described above in a different order than that implied by the specific presenter to obtain the preparative compound. [1] Compound.

[0283] Those skilled in the art will also recognize that the compound of Formula 1 and the intermediates described herein can undergo various electrophilic, nucleophilic, radical organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0284] Even without further explanation, it is believed that those skilled in the art will be able to utilize the invention to its fullest extent using the foregoing description. The following non-limiting examples illustrate the invention. The steps in the following examples illustrate the procedure for each step of the overall synthetic conversion, and the starting materials used for each step may not necessarily be prepared by the specific preparative run described in other examples or steps. Percentages are by weight, except for chromatographic solvent mixtures or otherwise specified. The parts and percentages of chromatographic solvent mixtures are by volume, unless otherwise stated. 1H NMR spectra are reported in ppm in the low-field region of tetramethylsilane; "s" represents a singlet, "d" represents a doublet, "t" represents a triplet, "q" represents a quartet, "m" represents a multiplet, "dd" represents a double doublet, "dt" represents a double triplet, and "br s" represents a broad singlet. Mass spectrometry (MS) describes the molecular weight of the highest isotopic abundance of the parent ion, which is formed by adding H+ (molecular weight 1) to the molecule (M+1) or by losing H+ (molecular weight 1) from the molecule (M-1). It is observed by using liquid chromatography combined with mass spectrometry (LCMS) and atmospheric pressure chemical ionization (AP+). "amu" represents the unified atomic mass unit.

[0285] The following non-limiting examples are intended to illustrate the use of preparative methods. [1] This method is used for compounds and corresponding intermediates. Unless otherwise stated, all NMR spectra are reported as CDCl3 in the low field region of tetramethylsilane at 500 MHz. Synthesis example 1 Preparation of N-[5-[(4,4-difluoro-1-piperidinyl)carbonyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (i.e., compound 241) Step A: Preparation of (4,4-difluoropiperidin-1-yl)(2,4-dimethyl-5-nitrophenyl) methyl ketone

[0286] Propylphosphonic anhydride (50 wt%, dissolved in ethyl acetate, 1.7 g, 2.7 mmol) was added to a stirred solution of dichloromethane (8 mL) containing 2,4-dimethyl-5-nitrobenzoic acid (0.30 g, 1.5 mmol), 4,4-difluoropiperidine (0.20 g, 1.7 mmol), and triethylamine (0.64 mL, 4.6 mmol). The reaction mixture was stirred overnight at room temperature, and then concentrated under reduced pressure. The mixture was diluted with hexane containing 50% ethyl acetate and filtered through a silicone mat. The filtrate was concentrated under reduced pressure to give the title compound as a yellow solid (0.57 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.87 (s, 1H), 7.24 (s, 1H), 4.11-3.97 (m, 1H), 3.92-3.77 (m, 1H), 3.43-3.36 (m, 2H), 2.62 (s, 3H), 2.36 (s, 3H), 2.15-2.07 (m, 2H), 1.99-1.86 (m, 2H). Step B: Preparation of (5-amino-2,4-dimethylphenyl)(4,4-difluoropiperidin-1-yl)methyl ketone

[0287] Ammonium chloride (0.10 g, 1.9 mmol) and iron powder (0.32 g, 5.7 mmol) were added to a stirred solution containing (4,4-difluoropiperidin-1-yl)(2,4-dimethyl-5-nitrophenyl) methyl ketone (i.e., the product of step A) (0.57 g) in ethanol (9 mL) and water (1 mL). The reaction mixture was stirred at 80 °C for 2 hours, then cooled to room temperature, diluted with ethyl acetate, and filtered through a Celite® diatomaceous earth filter aid, followed by a silica filter. The filtrate was concentrated under reduced pressure to give the title compound as an orange oil (0.40 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 6.90 (s, 1H), 6.48 (s, 1H), 4.07-3.99 (m, 1H), 3.81-3.73 (m, 1H), 3.57 (br s, 2H), 3.41-3.38 (m, 2H), 2.15 (sx 2, 6H), 2.11-2.02 (m, 2H), 1.92-1.83 (m, 2H). Step C: Preparation of N-[5-[(4,4-difluoro-1-piperidinyl)carbonyl]-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide

[0288] Triethylamine (0.27 mL, 1.9 mmol) was added at -40 °C to a stirred solution of dichloromethane (8 mL) containing (5-amino-2,4-dimethylphenyl)(4,4-difluoropiperidin-1-yl) methyl ketone (i.e., the product of step B) (0.40 g, 1.5 mmol), followed by dropwise addition of trifluoromethanesulfonic anhydride (0.27 mL, 1.6 mmol) over 5 minutes. The reaction mixture was stirred at -40 °C for 30 minutes and then poured into water. The layers were separated, the aqueous phase was extracted with ethyl acetate, and the combined organic extracts were concentrated under reduced pressure. The crude material was purified by column chromatography and extracted with ethyl acetate / hexane (gradient of 0 to 60% ethyl acetate, soluble in hexane) to give the title compound (i.e., the compound of this invention) as a white solid (0.26 g). 1H NMR (CDCl3) δ 9.61 (br s, 1H), 7.04 (s, 1H), 6.55 (s, 1H), 4.08-4.01 (m, 1H), 3.84-3.76 (m, 1H ), 3.34-3.28 (m, 2H), 2.25 (s, 6H), 2.13-2.03 (m, 2H), 1.92-1.82 (m, 2H). Synthesis example 2 Preparation of N-[2-chloro-5-[(4,4-difluoro-1-piperidinyl)carbonyl]-4-methylphenyl]-1,1,1-trifluoromethanesulfonamide (i.e., compound 229) Step A: Preparation of (4-chloro-2-methyl-5-nitrophenyl)(4,4-difluoropiperidin-1-yl)methyl ketone

[0289] Propylphosphonic anhydride (50 wt%, dissolved in ethyl acetate, 1.5 g, 2.4 mmol) was added to a stirred solution of dichloromethane (8 mL) containing 4-chloro-2-methyl-5-nitrobenzoic acid (0.30 g, 1.4 mmol), 4,4-difluoropiperidine (0.19 g, 1.6 mmol), and triethylamine (0.58 mL, 4.2 mmol). The reaction mixture was stirred overnight at room temperature, and then concentrated under reduced pressure. The mixture was diluted with hexane containing 50% ethyl acetate and filtered through a silicone mat. The filtrate was concentrated under reduced pressure to give the title compound as a grayish-white solid (0.39 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.76 (s, 1H), 7.44 (s, 1H), 4.06-3.95 (m, 1H), 3.86-3.74 (m, 1H), 3.39-3.35 (m, 2H), 2.36 (s, 3H), 2.12-2.04 (m, 2H), 1.98-1.85 (m, 2H). Step B: Preparation of (5-amino-4-chloro-2-methylphenyl)(4,4-difluoropiperidin-1-yl)methyl ketone

[0290] Ammonium chloride (65 mg, 1.2 mmol) and iron powder (0.21 g, 3.8 mmol) were added to a stirred solution containing (4-chloro-2-methyl-5-nitrophenyl)(4,4-difluoropiperidin-1-yl) methyl ketone (i.e., the product of step A) (0.39 g, 1.2 mmol) in 9 mL of ethanol and 1 mL of water. The reaction mixture was stirred at 80 °C for 2 hours, then cooled to room temperature, diluted with ethyl acetate, and filtered through a Celite® diatomaceous earth filter aid, followed by a silica filter. The filtrate was concentrated under reduced pressure to give the title compound as an orange oil (0.40 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.07 (s, 1H), 6.53 (s, 1H), 4.13-3.93 (m, 3H), 3.76-3.68 (m, 1H), 3.35-3.31 (m, 2H), 2.11 (s, 3H), 2.06-1.97 (m, 2H), 1.87-1.79 (m, 2H). Step C: Preparation of N-[2-chloro-5-[(4,4-difluoro-1-piperidinyl)carbonyl]-4-methylphenyl]-1,1,1-trifluoromethanesulfonamide

[0291] Triethylamine (0.25 mL, 1.8 mmol) was added at -10 °C to a stirred solution of dichloromethane (8 mL) containing (5-amino-4-chloro-2-methylphenyl)(4,4-difluoropiperidin-1-yl) methyl ketone (i.e., the product of step B) (0.40 g), followed by dropwise addition of trifluoromethanesulfonic anhydride (0.25 mL, 1.5 mmol) over 5 minutes. The reaction mixture was stirred at -10 °C for 30 minutes and then poured into water. The layers were separated, the aqueous phase was extracted with ethyl acetate, and the combined organic extracts were concentrated under reduced pressure. The crude material was purified by grinding with diethyl ether to give the title compound (i.e., the compound of this invention) as a white solid (0.24 g). 1H NMR (CDCl3) δ 9.23 (br s, 1H), 7.27 (s, 1H), 6.97 (s, 1H), 4.15-4.08 (m, 1H), 3.80-3.72 (m, 1H), 3.37-3.27 (m, 2H), 2.30 (s, 3H), 2.14-2.06 (m, 2H), 1.96-1.86 (m, 2H). Synthesis example 3 Preparation of 3-fluoro-N,N,2,4-tetramethyl-5-[[(trifluoromethyl)sulfonyl]amino]benzamide (i.e., compound 128) Step A: Preparation of 3-fluoro-2,4-dimethylbenzoic acid

[0292] 2,2,6,6-Tetramethylpiperidine (4.9 mL, 29 mmol) was slowly added at 0 °C to a stirred solution of anhydrous tetrahydrofuran (40 mL) containing n-butyllithium (1.6 M solution, dissolved in hexane, 18 mL, 29 mmol). The mixture was stirred for 15 min, then cooled to -78 °C, and a solution of anhydrous tetrahydrofuran (10 mL) containing 3-fluoro-4-methylbenzoic acid (2.0 g, 13 mmol) was added dropwise. The reaction mixture was stirred at -78 °C for 1.5 h, then warmed to -50 °C and stirred for an additional 45 min. Subsequently, iodomethane (3.2 mL, 52 mmol) was slowly added, and the reaction mixture was warmed to room temperature and stirred overnight. Water was added, and the mixture was washed with diethyl ether. The aqueous phase was acidified to pH 2 with 6 N hydrochloric acid and extracted with diethyl ether (x2). The combined organic extracts were then washed with brine (x1), dried over sodium sulfate, and concentrated under reduced pressure to give the title compound as a pale yellow solid (2.18 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.75 (d, 1H), 7.10-7.07 (m, 1H), 2.55 (d, 3H), 2.33 (d, 3H). Step B: Preparation of 3-fluoro-2,4-dimethyl-5-nitrobenzoic acid

[0293] Concentrated nitric acid (0.5 mL) was added dropwise to a stirred mixture containing concentrated sulfuric acid (6 mL) of 3-fluoro-2,4-dimethylbenzoic acid (i.e., the product of step A) (0.50 g, 3.0 mmol) at -20 °C. The reaction mixture was stirred between -20 °C and 0 °C for 2 hours, and then poured onto ice. The resulting solid was collected by filtration, washed with water (x1), and dried under vacuum to give a 1:1 mixture of the title compound and 3-fluoro-2,4-dimethyl-6-nitrobenzoic acid as a white solid (0.44 g), which was used in the next step without further purification. 1H NMR (a mixture of DMSO-d6, site-specific isomers) δ 8.24 (d, 1H), 8.06 (d, 1H), 2.52 (d, 3H), 2.45 (d, 3H), 2.34 (d, 3H), 2.26 (d, 3H). Step C: Preparation of 3-fluoro-N,N,2,4-tetramethyl-5-nitro-benzamide

[0294] Propylphosphonic anhydride (50 wt%, dissolved in ethyl acetate, 3.8 g, 6 mmol) was slowly added at 0 °C to a stirred solution of dichloromethane (10 mL) containing 3-fluoro-2,4-dimethyl-5-nitrobenzoic acid (i.e., the product of step B) (a mixture of 0.86 g of regiomeric isomers, including 2 mmol of the desired regiomeric isomer), dimethylamine hydrochloride (0.20 g, 2.5 mmol), and triethylamine (0.97 mL, 7 mmol). The reaction mixture was stirred overnight at room temperature, followed by washing with 1 N sodium hydroxide (x1), extraction of the aqueous phase with dichloromethane (x1), and washing of the combined organic extracts with brine (x1), drying with sodium sulfate, and concentration under reduced pressure. The crude material was purified by column chromatography by elution with ethyl acetate / hexane (gradient of 20–50% ethyl acetate, dissolved in hexane) to give the title compound as a pale yellow oil (0.39 g). 1H NMR (CDCl3) δ 7.66 (d, 1H), 3.15 (s, 3H), 2.88 (s, 3H), 2.50 (d, 3H), 2.28 (d, 3H). Step D: Preparation of 5-amino-3-fluoro-N,N,2,4-tetramethylbenzamide

[0295] An aqueous solution (5 mL) of ammonium chloride (1.36 g, 25.4 mmol) was added at 70 °C to a stirred solution containing 40 mL of ethanol (3.10 g, 12.9 mmol) of 3-fluoro-N,N,2,4-tetramethyl-5-nitrobenzylamine (the product of step C)). Subsequently, iron powder (2.17 g, 38.9 mmol) was added fractionally. After stirring for 1 hour, additional iron powder (0.30 g, 5.4 mmol) was added, and the reaction mixture was stirred overnight at 70 °C. The mixture was cooled to room temperature, diluted with ethyl acetate, and a Celite® diatomaceous earth filter aid was added. The mixture was filtered through a Celite® diatomaceous earth filter aid pad. Ethyl acetate and water were added to the filtrate, the layers were separated, and the aqueous phase was extracted with ethyl acetate (x1). The combined organic extracts were washed with a saturated ammonium chloride aqueous solution (x1), dried over sodium sulfate, filtered through a silicone pad, and concentrated under reduced pressure to give the title compound as a pale orange solid (2.68 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 6.32 (d, 1H), 3.63 (br s, 2H), 3.10 (s, 3H), 2.84 (s, 3H), 2.07-2.06 (m, 6H). Step E: Preparation of 3-fluoro-N,N,2,4-tetramethyl-5-((1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methyl)sulfonamido)benzamide

[0296] Triethylamine (5.3 mL, 38 mmol) was added at -78 °C to a stirred solution of dichloromethane (30 mL) containing 5-amino-3-fluoro-N,N,2,4-tetramethyl-benzylamine (i.e., the product of step D) (2.68 g, 12.7 mmol) and stirred over 20 minutes. Then, a solution of dichloromethane (10 mL) containing trifluoromethanesulfonic anhydride (5.1 mL, 30 mmol) was added dropwise. The reaction mixture was stirred at -20 °C for 1 hour and then poured into water. The layers were separated, and the aqueous phase was extracted with dichloromethane (x1). The combined organic extracts were dried over sodium sulfate, filtered through a silicone mat, and concentrated under reduced pressure. The crude material was purified by column chromatography (gradient from 5% to 30% ethyl acetate, dissolved in hexane) to give the title compound as a white solid (4.48 g). 1H NMR (CDCl3) δ 6.99 (s, 1H), 3.14 (s, 3H), 2.83 (s, 3H), 2.33 (d, 3H), 2.28 (d, 3H). Step F: Preparation of 3-fluoro-N,N,2,4-tetramethyl-5-[[(trifluoromethyl)sulfonyl]amino]benzamide

[0297] 1 N sodium hydroxide (20 mL, 20 mmol) was slowly added to a stirred solution containing 70 mL of dimethylbenzylamine (4.48 g, 9.4 mmol) of 5-[bis(trifluoromethylsulfonyl)amino]-3-fluoro-N,N,2,4-tetramethylbenzylamine (i.e., the product of step E)). The reaction mixture was stirred overnight at room temperature and then dried under reduced pressure to remove most of the dimethylbenzylamine. The mixture was diluted with water and acidified with 1 N hydrochloric acid, and the resulting precipitate was collected by filtration and washed with water (x2), diethyl ether (x1), and hexane (x1). The resulting material was purified by crystallization from methanol / water to give the title compound (i.e., the compound of this invention) as a white solid (2.32 g). 1H NMR (CDCl3) δ 10.50 (br s, 1H), 6.40 (s, 1H), 3.15 (s, 3H), 2.79 (s, 3H), 2.16 (m, 6H). Synthesis example 4 Preparation of N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (i.e., compound 197) Step A: Preparation of (2,4-dimethyl-5-nitrophenyl)methanol

[0298] A boranetetrahydrofuran complex (1M solution, dissolved in tetrahydrofuran, 200 mL, 0.2 mol) was added at -5 °C to a stirred solution of anhydrous tetrahydrofuran (275 mL) containing 2,4-dimethyl-5-nitrobenzoic acid (21.5 g, 0.11 mol). The reaction mixture was then allowed to warm to room temperature and stirred overnight. Methanol (12 mL) was slowly added, followed by a saturated aqueous solution of sodium bicarbonate (100 mL) and water (150 mL). The mixture was extracted with methyl tributyl ether (x2), and the combined organic extracts were washed with water (x1) and brine (x1), dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a pale yellow solid (20.0 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 8.07 (s, 1H), 7.14 (s, 1H), 4.73 (d, 2H), 2.58 (s, 3H), 2.37 (s, 3H). Step B: Preparation of 2,4-dimethyl-5-nitrobenzaldehyde

[0299] Celite® diatomaceous earth filter aid (~20 g) was added to a stirred solution of dichloromethane (330 mL) containing (2,4-dimethyl-5-nitrophenyl)methanol (i.e., the product of step A) (20.0 g, 0.11 mol), followed by fractional addition of pyridinium chlorochromate (28 g, 0.13 mol) over 1 hour. The reaction mixture was stirred overnight at room temperature and then filtered through a silica pad. The filtrate was concentrated under reduced pressure to give the title compound as a pale yellow solid (18.6 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 10.23 (s, 1H), 8.45 (s, 1H), 7.27 (s, 1H), 2.72 (s, 3H), 2.67 (s, 3H). Step C: Preparation of 2,4-dimethyl-5-nitro-benzaldehyde oxime

[0300] A hydroxylamine aqueous solution (50 wt%, dissolved in water, 13.2 g, 0.2 mol) was added dropwise (47 mL) to a stirred solution containing 2,4-dimethyl-5-nitrobenzaldehyde (i.e., the product of step B) (29.0 g, 0.16 mol) in 480 mL of methanol over 25 minutes. The reaction mixture was stirred overnight at room temperature, followed by drying under reduced pressure to remove most of the methanol. Water was added, the mixture was stirred, and the solid material was collected by filtration, washed with water, and dried under vacuum to give the title compound as a white solid (30.5 g, 11:1 E / Z), which was used in the next step without further purification. 1H NMR (CDCl3, E isomer) δ 8.34 (s, 1H), 8.33 (s, 1H), 7.51 (m, 1H), 7.17 (s, 1H), 2.59 (s, 3H), 2.46 (s, 3H). Step D: Preparation of N-hydroxy-2,4-dimethyl-5-nitro-imine benzyl chloride

[0301] N-chlorosuccinimide (22.1 g, 0.166 mol) was added fractionally over 2 hours to a stirred solution containing anhydrous N,N-dimethylformamide (160 mL) of 2,4-dimethyl-5-nitrobenzaldehyde oxime (i.e., the product of step C) (30.5 g, 0.157 mol), and the internal reaction temperature was maintained at 30°C. The reaction mixture was stirred at room temperature for an additional 3 hours, then poured into ice water and diluted with methyl tributyl ether. The layers were then separated, and the aqueous phase was extracted with methyl tributyl ether (x2). The combined organic extracts were washed with water (x3), 1 N hydrochloric acid, and saturated ammonium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a pale yellow solid (35.0 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 8.20 (s, 1H), 8.04-8.03 (m, 1H), 7.23 (s, 1H), 2.63 (s, 3H), 2.49 (s, 3H). Step E: Preparation of 3-(2,4-dimethyl-5-nitrophenyl)-1-oxa-2-azaspiro[4.5]dec-2-ene

[0302] Triethylamine (11.2 mL, 80 mmol) was added dropwise over 5 minutes to a stirred solution of chloroform (200 mL) containing N-hydroxy-2,4-dimethyl-5-nitro-imine benzyl chloride (i.e., the product of step D) (11.5 g, 50 mmol) and methylenecyclohexane (5.8 g, 60 mmol). The reaction mixture was stirred overnight at room temperature, then poured into water, and the layers were separated. The aqueous phase was extracted with dichloromethane, and the combined organic extracts were washed with 1 N hydrochloric acid (x1) and brine (x1), dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a viscous yellow oil (16.0 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.98 (s, 1H), 7.24 (s, 1H), 3.13 (s, 2H), 2.64 (s, 3H), 2.63 (s, 3H), 1.87-1.79 (m, 4H), 1.71-1.67 (m, 2H), 1.55-1.47 (m, 4H). Step F: Preparation of 2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)aniline

[0303] An aqueous solution of ammonium chloride (5.4 g, 0.10 mol) (20 mL) was added at 50 °C to a stirred solution of ethanol (180 mL) containing 16.0 g of 3-(2,4-dimethyl-5-nitro-phenyl)-1-oxa-2-azaspiro[4.5]dec-2-ene (i.e., the product of step E). Iron powder (8.4 g, 0.15 mol) was then added fractionally over 25 minutes, and the reaction mixture was heated from 50 °C to 70 °C. After further stirring at 70 °C for 30 minutes, the mixture was cooled to room temperature and filtered through a Celite® diatomaceous earth filter aid. The filtrate was concentrated under reduced pressure, followed by the addition of ethyl acetate and water. The layers were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with a saturated aqueous solution of ammonium chloride, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a viscous amber oil (13.0 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 6.93 (s, 1H), 6.67 (s, 1H), 3.54 (br s, 2H), 3.05 (s, 2H), 2.41 (s, 3H), 2.16 (s, 3H), 1.85-1.78 (m, 4H), 1.68-1.63 (m, 2H), 1.51-1.42 (m, 4H). Step G: Preparation of N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonylurea)methanesulfonamide

[0304] Triethylamine (21 mL, 0.15 mol) was added to a stirred solution of dichloromethane (180 mL) containing 2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)aniline (i.e., the product of step F) (13.0 g, 50 mmol). The mixture was cooled to -22°C, and then a solution of dichloromethane (20 mL, 0.12 mol) containing trifluoromethanesulfonic anhydride was added dropwise over 25 minutes. The reaction mixture was stirred between 0°C and 10°C for 1 hour, and then poured into water. The layers were separated, and the aqueous phase was extracted with dichloromethane. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and saturated ammonium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude material was purified by column chromatography (gradient of 0 to 10% methyl tributyl ether, dissolved in hexane) to give the title compound as a white solid (18.8 g). 1H NMR (CDCl3) δ 7.27 (s, 1H), 7.19 (s, 1H), 3.02 (s, 2H), 2.59 (s, 3H), 2.42 (s, 3H), 1.89-1.78 (m, 4H), 1.69-1.65 (m, 2H), 1.55-1.42 (m, 4H). Preparation of step H: N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide

[0305] 1 N sodium hydroxide (75 mL, 75 mmol) was added dropwise to a stirred solution containing N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonylmethanesulfonamide)methanesulfonamide (i.e., the product of step G) (18.8 g, 36 mmol) in 250 mL of dimethyl sulfonamide (250 mL). The reaction mixture was stirred overnight at room temperature and then dried under reduced pressure to remove most of the dimethyl sulfonamide. Water was added and the mixture was acidified with 1 N hydrochloric acid and then extracted with dichloromethane (x2). The combined organic extracts were washed with a saturated aqueous solution of ammonium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The crude material was purified by grinding with hot cyclohexane to give the title compound (i.e., the compound of the present invention) as a white solid (11.1 g). 1H NMR (CDCl3) δ 7.30 (s, 1H), 7.16 (s, 1H), 6.46 (s, 1H), 3.06 (s, 2H), 2.54 (s, 3H), 2.36 (s, 3H), 1.87-1.78 (m, 4H), 1.69-1.64 (m, 2H), 1.54-1.43 (m, 4H). Synthesis example 5 Preparation of methyl 2,2-dimethylpropionic acid [[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (i.e., compound 159)

[0306] Triethylamine (0.14 mL, 1.0 mmol) was added to a stirred solution of dichloromethane (8 mL) containing N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl]-1,1,1-trifluoro-methanesulfonamide (i.e., the product of Synthetic Example 4) (0.20 g, 0.51 mmol), followed by the addition of chloromethyl pivalate (0.11 mL, 0.76 mmol). The reaction mixture was stirred overnight at room temperature, followed by the addition of chloromethyl pivalate (0.15 mL, 1.0 mmol). The reaction mixture was stirred at 40 °C for 5 hours, followed by overnight at room temperature. The mixture was concentrated under reduced pressure, and the crude material was purified by column chromatography (gradient of 0 to 20% ethyl acetate, dissolved in hexane) to give the title compound (i.e., the compound of the present invention) as a clear, colorless oil (0.19 g). 1H NMR (CDCl3) δ 7.22 (s, 2H), 5.75 (d, 1H), 5.41 (d, 1H), 3.00 (m, 2H), 2.54 (s, 3H), 2.38 (s, 3H), 1.86-1.76 (m, 4H), 1.68-1.61 (m, 2H), 1.53-1.42 (m, 4H), 1.20 (s, 9H). Synthesis example 6 Preparation of N-[2,4-dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoazol-3-yl]phenyl]-1,1,1-trifluoromethanesulfonamide (i.e., compound 103) Step A: Preparation of 3-(2,4-dimethyl-5-nitro-phenyl)-4,5,6,6a-tetrahydro-3aH-cyclopentane[d]isoxaazole

[0307] Triethylamine (0.76 mL, 5.4 mmol) was added to a stirred solution of chloroform (8 mL) containing N-hydroxy-2,4-dimethyl-5-nitro-imine benzyl chloride (i.e., the product of step D in Synthetic Example 4) (0.50 g, 2.2 mmol), followed by the addition of cyclopentene (0.29 mL, 3.3 mmol). The reaction mixture was stirred overnight at room temperature, then dried under reduced pressure, and the crude material was purified by column chromatography (gradient from 0 to 20% ethyl acetate, soluble in hexane) to give the title compound as a white solid (0.41 g). 1H NMR (CDCl3) δ 8.05 (s, 1H), 7.25 (s, 1H), 5.23-5.20 (m, 1H), 4.16-4.12 (m, 1H), 2.62 (s, 3H), 2.58 (s, 3H), 2.23-2.19 (m, 1H), 1.92-1.74 (m, 4H), 1.58-1.47 (m, 1H). Step B: Preparation of 5-(4,5,6,6a-tetrahydro-3aH-cyclopentan[d]isoazol-3-yl)-2,4-dimethylaniline

[0308] Ammonium chloride (0.15 g, 2.8 mmol) and iron powder (0.26 g, 4.7 mmol) were added to a stirred solution containing 3-(2,4-dimethyl-5-nitro-phenyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isothiazide (i.e., the product of step A) (0.38 g, 1.5 mmol) in 9 mL of ethanol and 1 mL of water. The reaction mixture was stirred at 80 °C for 1 hour, then cooled to room temperature, diluted with ethyl acetate, and filtered through a Celite® diatomaceous earth filter aid, followed by a silica filter. The filtrate was concentrated under reduced pressure to give the title compound as a brown oil (0.35 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 6.92 (s, 1H), 6.67 (s, 1H), 5.11-5.09 (m, 1H), 4.05-4.02 (m, 1H), 3.57 (br s, 2H), 2.35 (s, 3H), 2.16-2.12 (m, 4H), 1.82-1.66 (m, 4H), 1.54-1.44 (m, 1H). Step C: Preparation of N-[5-(4,5,6,6a-tetrahydro-3aH-cyclopentane[d]isoazol-3-yl)-2,4-dimethyl-phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide

[0309] Triethylamine (0.59 mL, 4.2 mmol) was added to a stirred solution containing 10 mL of dichloromethane (0.33 g, 1.4 mmol) of 5-(4,5,6,6a-tetrahydro-3aH-cyclopentane[d]isoazol-3-yl)-2,4-dimethylaniline (i.e., the product of step B)). The mixture was cooled to -10 °C, and then trifluoromethanesulfonic anhydride (0.59 mL, 3.5 mmol) was added dropwise over 5 minutes. The reaction mixture was stirred at -10 °C for 20 minutes and then poured into water. The layers were separated, the aqueous phase was extracted with dichloromethane, and the combined organic extracts were concentrated under reduced pressure. The crude material was purified by column chromatography (gradient from 0 to 20% ethyl acetate, soluble in hexane) to give the title compound as a white solid (0.48 g). 1H NMR (CDCl3) δ 7.28 (s, 2H), 5.21-5.18 (m, 1H), 4.07-4.03 (m, 1H), 2.57 (s, 3H), 2.42 (s, 3H), 2.22-2.18 (m, 1H), 1.88-1.73 (m, 4H), 1.56-1.46 (m, 1H). Step D: Preparation of N-[2,4-dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopentane[d]isoazol-3-yl]phenyl]-1,1,1-trifluoromethanesulfonamide

[0310] 0.5 N sodium hydroxide (5 mL, 2.5 mmol) was added to a stirred solution containing N-[5-(4,5,6,6a-tetrahydro-3aH-cyclopentane[d]isoazol-3-yl)-2,4-dimethyl-phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide (i.e., the product of step C) (0.48 g, 0.97 mmol) dimethyl ethane (10 mL). The reaction mixture was stirred at room temperature for 1 hour, followed by drying under reduced pressure to remove most of the dimethyl ethane. The mixture was diluted with water, acidified with 1 N hydrochloric acid, and then extracted with ethyl acetate (x2). The combined organic extracts were washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (i.e., the compound of this invention) as a white solid (0.33 g). 1H NMR (CDCl3) δ 7.55 (br s, 1H), 7.22 (s, 1H), 7.12 (s, 1H), 5.18-5.15 (m, 1H), 4.06-4.02 (m, 1H), 2.42 (s, 3H), 2.33 (s, 3H), 2.17-2.14 (m, 1H), 1.83-1.70 (m, 4H), 1.52-1.42 (m, 1H). Synthesis Example 7 Preparation of methyl 2,2-dimethylpropionic acid [[2,4-dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopentane[d]isoazol-3-yl]phenyl][(trifluoromethyl)sulfonyl]amino] ester (i.e., compound 100)

[0311] Triethylamine (0.10 mL, 0.72 mmol) was added to a stirred solution of dichloromethane (8 mL) containing N-[5-(4,5,6,6a-tetrahydro-3aH-cyclopentan[d]isoazol-3-yl)-2,4-dimethyl-phenyl]-1,1,1-trifluoro-methanesulfonamide (i.e., the product of step D in Synthetic Example 6) (0.13 g, 0.36 mmol), followed by the addition of methyl neopentanoate (0.08 mL, 0.6 mmol). The reaction mixture was stirred overnight at room temperature, followed by the addition of triethylamine (0.10 mL, 0.72 mmol) and methyl neopentanoate (0.10 mL, 0.69 mmol). The reaction mixture was stirred overnight at room temperature. The mixture was concentrated under reduced pressure, and the crude material was purified by column chromatography (gradient of 0 to 20% ethyl acetate, dissolved in hexane) to give the title compound (i.e. the compound of the present invention) as a clear, colorless oil (79 mg). 1H NMR (CDCl3) δ 7.28-7.22 (m, 2H), 5.80-5.76 (m, 1H), 5.44-5.39 (m, 1H), 5.20-5.14 (m, 1H), 4.03-3.99 (m, 1H), 2.53-2.47 (m, 3H), 2.39 (m, 3H), 2.19-2.16 (m, 1H), 1.81-1.71 (m, 4H), 1.54-1.43 (m, 1H), 1.21-1.20 (m, 9H). Synthesis example 8 Preparation of N-[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4.5]dec-2-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (i.e., compound 278) Step A: Preparation of 2-(2,4-dimethyl-5-nitro-phenyl)-2-azaspiro[4.5]dec-1-one

[0312] Copper iodide (0.148 g, 10.0 mmol), tripotassium phosphate (K3PO4) (3.5 g, 16.4 mmol), and 2-azaspiro[4.5]dec-1-one (1.0 g, 6.5 mmol) were added to a 25 mL scintillation flask with spacers. The flask was evacuated and backfilled three times with nitrogen. In toluene (10 mL), trans-(1R,2R)N,N'-dimethylcyclohexane-1,2-diamine (0.246 mL, 20.0 mol%) and 1-bromo-2,4-dimethyl-5-nitrobenzene (1.8 g, 7.8 mmol) were combined and added to the reaction mixture via syringe. The reaction mixture was refluxed and stirred overnight under nitrogen, then diluted with ethyl acetate and filtered through a Celite® diatomaceous earth filter aid. The resulting filtrate was dried over magnesium sulfate and concentrated under reduced pressure to the residue. The residue was purified by column chromatography (0 to 80% ethyl acetate, dissolved in hexane gradient, 40 g column) to obtain the desired product, a yellow solid (1.85 g). 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.23 (s, 1H), 3.65 (m, 2H), 2.59 (s, 3H), 2.23 (s, 3H), 2.14-2.18 (m, 2H), 1.65-1.81 (m, 6H), 1.31-1.44 (m, 4H). Step B: Preparation of 2-(5-amino-2,4-dimethyl-phenyl)-2-azaspiro[4.5]dec-1-one

[0313] A 2 mL aqueous solution of ammonium chloride (0.728 g, 13.6 mmol) was added to a stirred solution containing 20 mL of ethanol (1.85 g, 6.8 mmol) of 2-(2,4-dimethyl-5-nitro-phenyl)-2-azaspiro[4.5]dec-1-one (i.e., the product of step A)). Then, iron powder (1.13 g, 20.3 mmol) was added, and the mixture was stirred at 80°C under nitrogen for 2 hours. Thin-layer chromatography showed that the reaction was partially complete at this point. A second equivalent of ammonium chloride and iron powder was added, and stirring continued overnight at 80°C. The mixture was cooled to room temperature and filtered through a Celite® diatomaceous earth filter aid. A second filtration through a Celite® diatomaceous earth filter aid was performed to remove turbidity. The filtrate was dried over magnesium sulfate and concentrated under reduced pressure to a yellow residue. The residue was purified by column chromatography (gradient of 20 to 100% ethyl acetate, dissolved in hexane, 40 g column) to give the title compound as a yellow solid (1.36 g). 1H NMR (CDCl3) δ 6.92 (s, 1H), 6.46 (s, 1H), 3.53-3.58 (m, 2H), 2.12 (s, 3H), 2.08 (m, 2H), 2.05 (s, 3H), 1.65-1.81 (m, 6H), 1.29-1.44 (m, 4H). Step C: Preparation of N-[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4,5]dec-2-yl)phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonylurea)methanesulfonamide

[0314] Triethylamine (0.562 mL, 4.03 mmol) was added to a stirred solution of dichloromethane (10 mL) containing 2-(5-amino-2,4-dimethyl-phenyl)-2-azaspiro[4.5]dec-1-one (i.e., the product of step B) (0.500 g, 1.84 mmol). The mixture was cooled to 0 °C, and then a solution of dichloromethane (10 mL) containing trifluoromethanesulfonic anhydride (0.677 mL, 4.03 mmol) was added dropwise over 5 minutes. The reaction mixture was then stirred overnight at room temperature. The reaction mixture was concentrated under vacuum. The crude material was purified by column chromatography (gradient from 0 to 100% ethyl acetate, dissolved in hexane, 40 g column) to give the title compound as a grayish-white solid (0.650 g). 1H NMR (CDCl3) δ 7.25 (s, 1H), 7.07 (s, 1H), 3.61 (m, 2H), 2.39 (s, 3H), 2.21 (s, 3H), 2.14 (m, 2H), 1.58-1.81 (m, 6H), 1.56-1.60, 1.29-1.52 (m, 4H). Step D: Preparation of N-[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4,5]dec-2-yl)phenyl]-1,1,1-trifluoromethanesulfonamide

[0315] A 1.0 N aqueous solution of sodium hydroxide (1 mL, 1.0 mmol) was added dropwise to a stirred solution containing N-[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4.5]dec-2-yl)phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonylurea)methanesulfonamide (i.e., the product of step C) (0.510 g, 0.951 mmol) of dimethyl sulfonamide (15 mL). The reaction mixture was stirred overnight at room temperature and then dried under reduced pressure to remove most of the dimethyl sulfonamide and water. The mixture was acidified with a few drops of 6 N aqueous hydrochloric acid to form a white precipitate. This precipitate was then filtered and dried under vacuum overnight to give the title compound (0.335 g). 1H NMR (CDCl3) δ 6.93 (s, 1H), 6.79 (s, 1H), 3.56 (m, 2H), 2.08-2.16 (m, 8H), 1.79 (m, 4H), 1.56 (m, 3H), 1.37 (m, 3H). Synthesis example 9 Preparation of methyl 2,2-dimethylpropionic acid [[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4.5]dec-2-yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (i.e., compound 268)

[0316] Triethylamine (0.103 mL, 0.740 mmol) and methyl neopentanoate (0.064 mL, 0.440 mmol) were added to a stirred solution containing 15 mL of dichloromethane (0.150 g, 0.370 mmol) of N-[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4.5]dec-2-yl)phenyl]-1,1,1-trifluoro-methanesulfonamide (i.e., the product of step D in Synthetic Example 8). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under vacuum. The residue was purified by column chromatography (0 to 100% ethyl acetate, dissolved in a hexane gradient, 12 g column) to give the title compound (i.e., the compound of the present invention) as a clear oil (0.092 g). 1H NMR (CDCl3) δ 7.22 (s, 1H), 7.05 (s, 1H), 5.71 (d, 1H), 5.42 (d, 1H), 3.53-3.63 (m, 2H), 2.38 (s, 3H), 2.19 (s, 3H), 2.10-2.15 (m, 2H), 2.05 (s, 1H), 1.57-1.82 (m, 4H), 1.47-1.52 (m, 1H), 1.30-1.51 (m, 3H), 1.20 (s, 9H). Synthesis example 10 Preparation of N-[5-(6-ethyl-2,3-dihydro-2-methyl-3-sideoxy-4-tert-yl)-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide (i.e., compound 34) Step A: Preparation of 2-(2,4-dimethyl-5-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-diborane

[0317] Bis(pinacol)diboron (3.4 g, 14 mmol) was added to a stirred solution containing 20 mL of dimethyl 5-nitrobenzene (2.30 g, 10 mmol), followed by the addition of potassium acetate (2.84 g, 30 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.35 g, 0.5 mmol). The reaction mixture was heated to 110 °C and stirred overnight. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, and filtered through a Celite® diatomaceous earth filter aid. The reaction mixture was concentrated under vacuum. The crude material was purified by column chromatography to give the title compound (4.10 g). 1H NMR (CDCl3) δ 8.40 (s, 1H), 7.10 (s, 1H), 2.57 (s, 3H), 2.56 (s, 3H), 1.35 (s, 12H). Step B: Preparation of 6-ethyl-4-iodo-2-methyl-tert-3-one

[0318] TMPZn·LiCl (14 mL, 9.6 mmol, 0.7 M, soluble in tetrahydrofuran) was added to a stirred solution of tetrahydrofuran (10 mL) containing 6-ethyl-2-methyl-dacryl-3-one (0.95 g, 6.9 mmol). The reaction mixture was heated to room temperature and stirred for 1 hour. Iodine (2.7 g, 10.3 mmol) was then added, and the reaction mixture was stirred overnight at room temperature. A saturated aqueous solution of ammonium chloride was added, and the aqueous phase was extracted with ethyl acetate (x3). The combined organic layers were washed with Na2SO3 and subsequently with brine. The combined organic extracts were dried (MgSO4), filtered, and concentrated under vacuum. Purification was achieved by column chromatography (gradient from 0 to 100% ethyl acetate, soluble in hexane) to give the title compound (290 mg). 1H NMR (CDCl3) δ 7.81 (d, 1H), 3.81 (s, 3H), 2.62 (m, 2H), 1.23 (m, 3H). Step C: Preparation of 4-(2,4-dimethyl-5-nitro-phenyl)-6-ethyl-2-methyl-tert-3-one

[0319] 2-(2,4-dimethyl-5-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-diborane (i.e., the product of step A) (0.39 g, 1.4 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.035 mg, 0.05 mmol), and sodium carbonate (2 N, dissolved in H₂O, 1 mL) were added to a stirred solution containing 2 mL of dioxane (0.26 g, 1 mmol) of 6-ethyl-4-iodo-2-methyl-daphnia-3-onebenzylamine (i.e., the product of step B) and heated to 80 °C over 3 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, and filtered through Celite® diatomaceous earth filter aid. The reaction mixture was concentrated under vacuum. The crude material was purified by column chromatography to give the title compound (0.28 g). 1H NMR (CDCl3) δ 7.92 (s, 1H), 7.25 (s, 1H), 7.11 (s, 1H), 3.86 (s, 3H), 2.68 (m, 2H), 2.63 (s, 3H), 2.30 (s, 3H), 1.26 (m, 3H). Step D: Preparation of 4-(5-amino-2,4-dimethyl-phenyl)-6-ethyl-2-methyl-tert-3-one

[0320] An aqueous solution of ammonium chloride (0.16 g, 3 mmol) (2 mL) was added at 70 °C to a stirred solution containing 18 mL of ethanol (0.28 g, 1 mmol) of 4-(2,4-dimethyl-5-nitro-phenyl)-6-ethyl-2-methyl-daphne-3-one (i.e., the product of step C) (0.28 g, 1 mmol). Subsequently, iron powder (0.17 g, 3 mmol) was added fractionally, and the reaction mixture was stirred for 3 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a Celite® diatomaceous earth filter aid. Ethyl acetate and water were added to the filtrate, the layers were separated, and the aqueous phase was extracted with ethyl acetate (x1). The combined organic extracts were washed with a saturated aqueous solution of ammonium chloride (x1), dried over sodium sulfate, filtered through a silicone pad, and concentrated under reduced pressure to give the title compound (0.21 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.05 (s, 1H), 6.97 (s, 1H), 6.61 (s, 1H), 3.81 (s, 3H), 2.66 (m, 2H), 2.19 (s, 3H), 2.11 (s, 3H), 1.25 (m, 3H). Step E: Preparation of N-[5-(6-ethyl-2-methyl-3-sideoxy-4-yl)-2,4-dimethyl-phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonylurea)methanesulfonamide

[0321] Triethylamine (0.13 mL, 0.9 mmol) was added at -78 °C to a stirred solution of dichloromethane (3 mL) containing 4-(5-amino-2,4-dimethyl-phenyl)-6-ethyl-2-methyl-tazo-3-one (i.e., the product of step D) (0.2 g, 0.7 mmol), followed by dropwise addition of dichloromethane (2 mL) containing trifluoromethanesulfonic anhydride (0.11 mL, 0.9 mmol) over 20 minutes. Silicone was added to the reaction mixture, and the solvent was removed under vacuum. The crude material was purified by column chromatography (gradient of 5 to 30% ethyl acetate, dissolved in hexane) to give the title compound (0.08 g) and N-[5-(6-ethyl-2-methyl-3-sideoxy-tazo-4-yl)-2,4-dimethyl-phenyl]-1,1,1-trifluoro-methanesulfonamide (i.e. the product of step F in this synthetic example) (0.13 g). 1H NMR (CDCl3) δ 7.28 (s, 1H), 7.20 (s, 1H), 7.06 (s, 1H), 3.83 (s, 3H), 2.71 (m, 2H), 2.43 (s, 3H), 2.29 (s, 3H), 1.27 (m, 3H). Step F: Preparation of N-[5-(6-ethyl-2,3-dihydro-2-methyl-3-sideoxy-4-tert-yl)-2,4-dimethylphenyl]-1,1,1-trifluoromethanesulfonamide

[0322] 1 N sodium hydroxide (0.5 mL, 0.5 mmol) was slowly added to a stirred solution containing N-[5-(6-ethyl-2-methyl-3-sideoxy-4-yl)-2,4-dimethyl-phenyl]-1,1,1-trifluoro-N-(trifluoromethylsulfonylmethanesulfonamide)methanesulfonamide (i.e., the product of step E) (0.08 g) in 2 mL of dimethyl sulfonamide. The reaction mixture was stirred overnight at room temperature, followed by vacuum concentration. The crude material was acidified, treated, and purified by column chromatography to give the title compound (i.e., the compound of this invention) as a white solid (0.025 g). 1H NMR (CDCl3) δ 9.78 (s, 1H), 7.07 (s, 1H), 6.92 (s, 1H), 6.89 (s, 1H), 3.90 (s, 3H), 2.71 (m, 2H), 2.16 (s, 3H), 2.15 (s, 3H), 1.27 (m, 3H). Synthesis example 11 Preparation of N-[2,4-dimethyl-5-(1,2,3,4-tetrahydro-1,3-dimethyl-2,4-disidero-5-pyrimidinyl)phenyl]-1,1,1-trifluoromethanesulfonamide (i.e., compound 49) Step A: Preparation of 5-(2,4-dimethyl-5-nitro-phenyl)-1,3-dimethyl-pyrimidine-2,4-dione

[0323] 2-(2,4-dimethyl-5-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-diborane (i.e., the product of step A in Synthetic Example 10) (1.1 g, 3.9 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.11 g, 0.15 mmol), and sodium carbonate (2 N, dissolved in H₂O, 3 mL) were added to a stirred solution of diborane (6 mL) containing 5-bromo-1,3-dimethylpyrimidine-2,4-dione (0.65 g, 3 mmol), and the reaction mixture was heated to 80°C over 3 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, and filtered through Celite® diatomaceous earth filter aid. The reaction mixture was concentrated under vacuum. The crude material was purified by column chromatography to give the title compound (0.72 g). 1H NMR (CDCl3) δ 7.84 (s, 1H), 7.29 (s, 1H), 7.25 (s, 1H), 3.49 (s, 3H), 3.42 (s, 3H), 2.62 (s, 3H), 2.29 (s, 3H). Step B: Preparation of 5-(5-amino-2,4-dimethyl-phenyl)-1,3-dimethyl-pyrimidine-2,4-dione

[0324] An aqueous solution of ammonium chloride (0.16 g, 3 mmol) (2 mL) was added at 70 °C to a stirred solution containing 18 mL of ethanol (0.29 g, 1 mmol) of 5-(2,4-dimethyl-5-nitro-phenyl)-1,3-dimethyl-pyrimidin-2,4-dione (i.e., the product of step A)). Iron powder (0.17 g, 3 mmol) was then added fractionally, and the reaction mixture was stirred for 3 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a Celite® diatomaceous earth filter aid. Ethyl acetate and water were added to the filtrate, the layers were separated, and the aqueous phase was extracted with ethyl acetate (x1). The combined organic extracts were washed with a saturated aqueous solution of ammonium chloride (x1), dried over sodium sulfate, filtered through a silicone pad, and concentrated under reduced pressure to give the title compound (0.21 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.11 (s, 1H), 6.92 (s, 1H), 6.49 (s, 1H), 3.44 (s, 3H), 3.41 (s, 3H), 2.15 (s, 3H), 2.09 (s, 3H). Step C: Preparation of N-[2,4-dimethyl-5-(1,2,3,4-tetrahydro-1,3-dimethyl-2,4-disideloxy-5-pyrimidinyl)phenyl]-1,1,1-trifluoromethanesulfonamide

[0325] Triethylamine (0.13 mL, 0.97 mmol) was added at -78 °C to a stirred solution of dichloromethane (3 mL) containing 5-(5-amino-2,4-dimethyl-phenyl)-1,3-dimethyl-pyrimidin-2,4-dione (i.e., the product of step B) (0.21 g, 0.81 mmol), followed by dropwise addition of dichloromethane (2 mL) containing trifluoromethanesulfonic anhydride (0.11 mL, 0.9 mmol) over 20 minutes. Silica gel was added to the reaction mixture, and the solvent was removed under vacuum. The crude material was purified by column chromatography (gradient from 5 to 100% ethyl acetate, dissolved in hexane) to give the title compound (i.e., the compound of this invention) as a white solid (0.11 g). 1H NMR (CDCl3) δ 8.18 (s, 1H), 7.18 (s, 1H), 7.01 (s, 1H), 6.92 (s, 1H), 3.47 (s, 3H), 3.45 (s, 3H), 2.18 (s, 3H), 2.16 (s, 3H). Synthesis example 12 Preparation of 1,1,1-trifluoro-N-[2,3,4-trimethyl-5-(4-pyrinylcarbonyl)phenyl]methanesulfonamide (i.e., compound 289) Step A: Preparation of 2,3,4-trimethylbenzaldehyde

[0326] 1,1-Dichlorodimethyl ether (3.6 mL, 40 mmol) was added at 0 °C to a stirred solution of dichloromethane (35 mL) containing 1,2,3-trimethylbenzene (3 g, 25 mmol), followed by dropwise addition of titanium tetrachloride (1 M solution, dissolved in dichloromethane, 27.5 mL, 27.5 mmol). The reaction mixture was stirred at 0 °C for 2 hours, then poured into ice water (300 mL). Dichloromethane (100 mL) was added, and the mixture was stirred vigorously for 10 minutes, followed by separation of the layers. The aqueous phase was extracted with dichloromethane (x1), and the combined organic extracts were washed with water and brine and concentrated under reduced pressure to give the title compound as a pale yellow oil (3.1 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 10.26 (s, 1H), 7.56 (d, 1H), 7.16 (d, 1H), 2.61 (s, 3H), 2.36 (s, 3H), 2.24 (s, 3H). Step B: Preparation of 2,3,4-trimethylbenzoic acid

[0327] Potassium permanganate (6.61 g, 41.8 mmol) was added fractionally to a stirred solution containing 20 mL of acetone and 10 mL of water (3.1 g) of 2,3,4-trimethylbenzaldehyde (the product of step A). ​​The reaction mixture was then allowed to warm to room temperature and stirred overnight. The mixture was filtered through a Celite pad, washed with water and acetone, and the filtrate was acidified to pH ~2 with 1 N hydrochloric acid and extracted with ethyl acetate (x2). The combined organic extracts were washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a white solid (2.6 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.74 (d, 1H), 7.08 (d, 1H), 2.57 (s, 3H), 2.35 (s, 3H), 2.25 (s, 3H). Step C: Preparation of 2,3,4-trimethyl-5-nitrobenzoic acid

[0328] Concentrated nitric acid (0.8 mL) was added dropwise to concentrated sulfuric acid (0.7 mL) at 0 °C, and the mixture was stirred for 5 minutes. Subsequently, this mixture was added dropwise to a stirred mixture containing concentrated sulfuric acid (8 mL) of 2,3,4-trimethylbenzoic acid (i.e., the product of step B) (1.5 g) at 5 °C. The reaction mixture was stirred between 0 °C and 5 °C for 2 hours, and then poured into ice water (200 mL). The mixture was extracted with ethyl acetate (x2), and the combined organic extracts were washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a brown solid (1.82 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 8.24 (s, 1H), 2.64 (s, 3H), 2.46 (s, 3H), 2.36 (s, 3H). Step D: Preparation of α-linyl-(2,3,4-trimethyl-5-nitro-phenyl) ketone

[0329] Triethylamine (0.4 mL, 2.9 mmol) and α-oxoline (0.1 mL, 1.1 mmol) were added to a stirred mixture containing chloroform (8 mL) of 2,3,4-trimethyl-5-nitrobenzoic acid (i.e., the product of step C) (0.20 g), followed by the addition of propylphosphonic anhydride (50 wt%, dissolved in ethyl acetate, 1.2 g, 1.9 mmol). The reaction mixture was stirred at 60 °C for 3 hours, then cooled to room temperature and concentrated under reduced pressure. The crude material was purified by column chromatography (gradient of 0–60% ethyl acetate, dissolved in hexane) to give the title compound as a yellow oil (0.19 g). 1H NMR (CDCl3) δ 7.43 (s, 1H), 3.803.73 (m, 4H), 3.603.50 (m, 2H), 3.263.16 (m, 2H), 2.37 (s, 3H), 2.27 (s, 6H). Step E: Preparation of (5-amino-2,3,4-trimethyl-phenyl)-α-linyl-methyl ketone

[0330] Ammonium chloride (75 mg, 1.4 mmol) and iron powder (0.12 g, 2.1 mmol) were added to a stirred mixture containing α-linyl-(2,3,4-trimethyl-5-nitro-phenyl) ketone (i.e., the product of step D) (0.19 g, 0.70 mmol) in 9 mL of ethanol and 1 mL of water. The reaction mixture was stirred at 80 °C for 2 hours, then cooled to room temperature, diluted with ethyl acetate, and filtered through a Celite® pad followed by a silica pad. The filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (0.14 g), which was used in the next step without further purification. 1H NMR (CDCl3) δ 6.26 (s, 1H), 3.793.55 (m, 6H), 3.533.51 (m, 2H), 3.233.20 (m, 2H), 2.15 (s, 3H), 2.09 (s, 3H), 2.06 (s, 3H). Step F: Preparation of 1,1,1-trifluoro-N-(trifluoromethylsulfonyl)-N-[2,3,4-trimethyl-5-(othioline-4-carbonyl)phenyl]methanesulfonamide

[0331] Triethylamine (0.24 mL, 1.7 mmol) was added at -10 °C to a stirred solution containing (5-amino-2,3,4-trimethyl-phenyl)-α-linyl-methyl ketone (i.e., the product of step E) (0.14 g) in dichloromethane (8 mL), followed by dropwise addition of trifluoromethanesulfonic anhydride (0.19 mL, 1.1 mmol). The reaction mixture was stirred between 0 °C and 10 °C for 1 hour, followed by the addition of water. The layers were separated, and the organic phase was concentrated under reduced pressure. The crude material was purified by column chromatography (gradient of 0-60% ethyl acetate, dissolved in hexane) to give the title compound as a clear, colorless oil (0.15 g). 1H NMR (CDCl3) δ 6.99 (s, 1H), 3.83-3.73 (m, 4H), 3.60-3.51 (m, 2H), 3.24-3.15 (m, 2H), 2.31 (s, 3H), 2.29 (s, 3H), 2.27 (s, 3H). Step G: Preparation of 1,1,1-trifluoro-N-[2,3,4-trimethyl-5-(othioline-4-carbonyl)phenyl]methanesulfonamide

[0332] 0.5 N sodium hydroxide (3.6 mL, 1.8 mmol) was added to a stirred solution containing 8 mL of dimethyl sulfonamide (0.15 g, 0.30 mmol) of 1,1,1-trifluoro-N-(trifluoromethylsulfonyl)-N-[2,3,4-trimethyl-5-(othioline-4-carbonyl)phenyl]methanesulfonamide (i.e., the product of step F)). The reaction mixture was stirred at room temperature for 2 hours, followed by drying under reduced pressure to remove the dimethyl sulfonamide. The mixture was diluted with water, acidified to pH ~2 with 1 N hydrochloric acid, and then extracted with ethyl acetate (x2). The combined organic extracts were washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (i.e., the compound of this invention) as a white solid (0.10 g). 1H NMR (CDCl3) δ 10.16 (br s, 1H), 6.45 (s, 1H), 3.853.82 (s, 2H), 3.783.75 (s, 2H), 3.57 (m, 2H), 3.193.11 (m, 2H), 2.19 (s, 3H), 2.15 (s, 3H), 2.13 (s, 3H). Synthesis example 13 Preparation of methyl 2,2-dimethylpropionic acid [[(trifluoromethyl)sulfonyl][2,3,4-trimethyl-5-(4-hydroxylinylcarbonyl)phenyl]amino] ester (i.e., compound 324)

[0333] Sodium bicarbonate (80 mg, 0.95 mmol), tetrabutylammonium bromide (87 mg, 0.27 mmol), and chloromethyl neopentanoate (0.12 mL, 0.81 mmol) were added to a stirred solution containing acetonitrile (8 mL) of 1,1,1-trifluoro-N-[2,3,4-trimethyl-5-(4-hydroxylinylcarbonyl)phenyl]methanesulfonamide (i.e., the product of Synthesis Example 12, 0.10 g, 0.27 mmol). The reaction mixture was stirred at 80°C for 3 hours, then cooled to room temperature and concentrated under reduced pressure. The crude material was purified by column chromatography (gradient of 0–50% ethyl acetate, soluble in hexane) to give the title compound (i.e., the compound of the present invention) as a clear, colorless oil (93 mg). 1H NMR (CDCl3) δ 6.97 - 6.93 (m, 1H), 5.795.67 (m, 1H), 5.455.37 (m, 1H), 3.933.68 (m, 4H), 3.593.50 (m, 2H), 3.253.16 (m, 2H), 2.312.29 (m, 3H), 2.25 (s, 6H), 1.19 (s, 9H).

[0334] The compounds listed in Tables 1 to 11 below can be prepared using the methods described herein and methods known in the art. The abbreviations used in the tables are as follows: "t" indicates tertiary, "s" indicates secondary, "n" indicates normal, "i" indicates iso, "c" indicates cyclic, "Me" indicates methyl, "Et" indicates ethyl, "Pr" indicates propyl, "Bu" indicates butyl, "n-Pr" indicates 1-propyl, "i-Pr" indicates isopropyl, "Bu" indicates butyl, "c-Pr" indicates cyclopropyl, "c-Bu" indicates cyclobutyl, "i-Bu" indicates cyclopropyl, and so on. Isobutyl, "Ph" means phenyl, "OMe" means methyl thio, "OEt" means ethoxy, "SMe" means methyl thio, "SEt" means ethyl thio, "NHMe" means methyl amino, "-CN" means cyano, "Py" means pyridyl, "-NO2" means nitro, "TMS" means trimethylsilyl, "S(O)Me" means methyl sulfinyl, and "S(O)2Me" means methyl sulfinyl. Table 1 G is CO-J and J is J-1 J-2 J-3 J-4 J-5 J-6 J-7 J-8 J-9 J-10 J-11 J-12 J-13 J-14 J-15 J-16 J-17 J-18 J-19 J-20 J-21 J-22 J-23 J-24 J-25 J-26 J-27 J-28 J-29 J-30 J-31 J-32 J-33 J-34 J-35 J-36 J-37 J-38 J-39 J-40 J-41 J-42 J-43 J-44 J-45 J-46 J-47 J-48 J-49 J-50 J-51 J-52 J-53 J-54 J-3a* J-3b* See List 1, J-1 to J-52. Table 2 G is CO-K and K is K-1 K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9 See List 2, K-1 through K-9. Table 3 G is CO-J or CO-K; and J or K is... J-1 J-2 J-3 J-4 J-5 J-6 J-7 J-8 J-9 J-10 J-11 J-12 J-13 J-14 J-15 J-16 J-17 J-18 J-19 J-20 J-21 J-22 J-23 J-24 J-25 J-26 J-27 J-28 J-29 J-30 J-31 J-32 J-33 J-34 J-35 J-36 J-37 J-38 J-39 J-40 J-41 J-42 J-43 J-44 J-45 J-46 J-47 J-48 J-49 J-50 J-51 J-52 J-53 J-54 J-3a* J-3b* K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9 K-1 See List 1, J-1 to J-52; and List 2, K-1 to K-9. Table 4 G is CO-J and J is J-1 J-2 J-3 J-4 J-5 J-6 J-7 J-8 J-9 J-10 J-11 J-12 J-13 J-14 J-15 J-16 J-17 J-18 J-19 J-20 J-21 J-22 J-23 J-24 J-25 J-26 J-27 J-28 J-29 J-30 J-31 J-32 J-33 J-34 J-35 J-36 J-37 J-38 J-39 J-40 J-41 J-42 J-43 J-44 J-45 J-46 J-47 J-48 J-49 J-50 J-51 J-52 J-53 J-54 J-3a* J-3b* See List 1, J-1 to J-54. Table 5 G is CO-K and K is K-1 K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9 See List 2, K-1 through K-9. Table 6 G is CO-J and J is J-1 J-2 J-3 J-4 J-5 J-6 J-7 J-8 J-9 J-10 J-11 J-12 J-13 J-14 J-15 J-16 J-17 J-18 J-19 J-20 J-21 J-22 J-23 J-24 J-25 J-26 J-27 J-28 J-29 J-30 J-31 J-32 J-33 J-34 J-35 J-36 J-37 J-38 J-39 J-40 J-41 J-42 J-43 J-44 J-45 J-46 J-47 J-48 J-49 J-50 J-51 J-52 J-53 J-54 J-3a* J-3b* K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9 K-1 See List 1, J-1 through J-54; and List 2, K-1 through K-9. Table 7 G is G-1-1 G-1-1a G-1-1b G-1-2 G-1-3 G-1-4 G-1-5 G-1-6 G-1-7 G-1-8 G-1-8a G-1-8b G-1-9 G-1-10 G-1-11 G-1-12 G-1-13 G-1-14 G-1-15 G-1-16 G-1-17 G-1-18 G-1-19 G-1-20 G-1-21 G-1-22 G-1-23 G-1-24 G-1-25 G-1-26 G-1-27 G-1-24a G-1-24b G-1-28a* G-1-28b* G-1-29 G-1-30 G-1-31 G-1-32 G-1-33 G-1-33a* G-1-33b* G-1-34 G-1-34a* G-1-34b* G-1-35 G-1-35a* G-1-35b* G-1-36 G-1-37 G-1-38 G-1-38a* G-1-38b* G-1-1aa G-1-1ab G-1-8aa G-1-8ab See List 3, G-1-1 to G-1-27. Table 8 G is G-2-1 G-2-2 G-2-3 G-2-4 G-2-5 G-2-6 G-2-7 G-2-8 G-2-9 G-2-10 G-2-11 G-2-12 G-2-13 G-2-14 G-2-15 G-2-16 G-2-17 See G-2-1 to G-2-12 in List 4. Table 9 R13 R14 R15 Me Me H Me Me Me Me Me Cl Me Et H Me Et Me Me Et Cl Et Me H Et [[ID= 64]] Me Me Et Me Cl Et Et H Et Et Me Et Et Cl i- Pr Me H i- Pr Me Me i- Pr Me Cl i- Pr Et H i-Pr Et Me i-Pr Et Cl CH2OCH3 Me H CH2OCH3 Me Me CH2OCH3 Me Cl CH2OCH3 Et H CH2OCH2CH3 Et Me CH2OCH3 Et Cl Table 10 R13 R15 R16 R13 R15 R16 Me H H i-Pr H H Me H Cl i- Pr H Cl Me H Me i-Pr H Me Me Cl H i- Pr Cl H Me Cl Cl i-Pr Cl Cl Me Cl Me i-Pr Cl Me Me Me H i-Pr Me H Me Me Cl i-Pr Me Cl Me Me Me i-Pr Me Me Et H H c-Pr H H Et H Cl c-Pr H Cl Et H Me c-Pr H Me Et Cl H c-Pr Cl H Et Cl Cl c-Pr Cl Cl Et Cl Me c-Pr Cl Me Et Me H c-Pr Me H Et Me Cl c-Pr Me Cl Et Me Me c-Pr Me Me Table 11 R16 R17 R18 H Me H H Me Me H Et H H Et Me Me Me H Me Me Me Me Et H Me Et Me Cl Me H Cl Me Me Cl Et H Cl Et Me Table 12 G is CO-J and J is J-1 J-2 J-3 J-4 J-5 J-6 J-7 J-8 J-9 J-10 J-11 J-12 J-13 J-14 J-15 J-16 J-17 J-18 J-19 J-20 J-21 J-22 J-23 J-24 J-25 J-26 J-27 J-28 J-29 J-30 J-31 J-32 J-33 J-34 J-35 J-36 J-37 J-38 J-39 J-40 J-41 J-42 J-43 J-44 J-45 J-46 J-47 J-48 J-49 J-50 J-51 J-52 J-53 J-54 J-3a* J-3b* See List 1, J-1 through J-54. Table 13 G is CO-K and K is K-1 K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9 See List 2, K-1 through K-9. Table 14 G is CO-J or CO-K; and J or K is... J-1 J-2 J-3 J-4 J-5 J-6 J-7 J-8 J-9 J-10 J-11 J-12 J-13 J-14 J-15 J-16 J-17 J-18 J-19 J-20 J-21 J-22 J-23 J-24 J-25 J-26 J-27 J-28 J-29 J-30 J-31 J-32 J-33 J-34 J-35 J-36 J-37 J-38 J-39 J-40 J-41 J-42 J-43 J-44 J-45 J-46 J-47 J-48 J-49 J-50 J-51 J-52 J-53 J-54 J-3a* J-3b* K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9 K-1 See List 1, J-1 to J-54; and List 2, K-1 to K-9. Table 15 G is CO-J and J is J-1 J-2 J-3 J-4 J-5 J-6 J-7 J-8 J-9 J-10 J-11 J-12 J-13 J-14 J-15 J-16 J-17 J-18 J-19 J-20 J-21 J-22 J-23 J-24 J-25 J-26 J-27 J-28 J-29 J-30 J-31 J-32 J-33 J-34 J-35 J-36 J-37 J-38 J-39 J-40 J-41 J-42 J-43 J-44 J-45 J-46 J-47 J-48 J-49 J-50 J-51 J-52 J-53 J-54 J-3a* J-3b* See List 1, J-1 to J-54 Table 16 G is CO-K and K is K-1 K-2 K-3 K-4 K-5 K-6 K-7 K-8 K-9 See List 2, K-1 through K-9. Table 17 G is G-1-1 G-1-1a G-1-1b G-1-2 G-1-3 G-1-4 G-1-5 G-1-6 G-1-7 G-1-8 G-1-8a G-1-8b G-1-9 G-1-10 G-1-11 G-1-12 G-1-13 G-1-14 G-1-15 G-1-16 G-1-17 G-1-18 G-1-19 G-1-20 G-1-21 G-1-22 G-1-23 G-1-24 G-1-25 G-1-26 G-1-27 G-1-24a G-1-24b G-1-28a* G-1-28b* G-1-29 G-1-30 G-1-31 G-1-32 G-1-33 G-1-33a* G-1-33b* G-1-34 G-1-34a* G-1-34b* G-1-35 G-1-35a* G-1-35b* G-1-36 G-1-37 G-1-38 G-1-38a* G-1-38b* G-1-1aa G-1-1ab G-1-8aa G-1-8ab See List 3, G-1-1 to G-1-27. Table 18 G is G-2-1 G-2-2 G-2-3 G-2-4 G-2-5 G-2-6 G-2-7 G-2-8 G-2-9 G-2-10 G-2-11 G-2-12 G-2-13 G-2-14 G-2-15 G-2-16 G-2-17 See List 4, G-2-1 to G-2-12. Table 19 R13 R14 R15 Me Me H Me Me Me Me Me Cl Me And H Me And Me Me And Cl And Me H And Me Me And Me Cl And And H And And Me And And Cl i- Pr Me H i- Pr Me Me i- Pr Me Cl i- Pr And H i-Pr And Me i-Pr And Cl CH2OCH3 Me H CH2OCH3 Me Me CH2OCH3 Me Cl CH2OCH3 Et H CH2OCH2CH3 Et Me CH2OCH3 Et[[ID=2】] Cl Table 20 R13 R15 R16 R13 [[ID=】] R15 R16 Me H H i-Pr H H Me H Cl i- Pr H<】 Cl Me H Me i-Pr H Me Me Cl H i- Pr Cl H Me Cl Cl i-Pr Cl Cl Me Cl Me i-Pr Cl Me Me Me H i-Pr Me H Me Me Cl i-Pr Me Cl Me Me Me i-Pr Me Me Et H H c-Pr H H Et H Cl c-Pr H Cl Et H Me c-Pr H Me Et Cl H c-Pr Cl H Et Cl Cl c-Pr Cl Cl Et Cl Me c-Pr Cl Me Et Me H c-Pr Me H Et Me Cl c-Pr Me Cl Et Me Me c-Pr Me Me Table 21 R16 R17 R18 H Me H H Me Me H Et H H Et Me Me Me H Me Me Me Me Et H Me Et Me Cl Me H Cl Me Me Cl Et H Cl Et Me ​​The compounds of the present invention are typically used as the herbicidal active ingredient (i.e., formulation) in a composition together with at least one additional component (as a carrier) selected from the group consisting of surfactants, solid diluents and liquid diluents. These formulations or compositional components are selected to be consistent with the physical properties, application mode, and environmental factors (such as soil type, humidity, and temperature) of the active ingredient.

[0336] Applicable formulations include both liquid and solid components. Liquid components include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates, and / or suspension emulsions) and the like, which can be selectively thickened into colloids. Aqueous liquid components generally take the form of soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, flowable concentrates, and suspension emulsions. Non-aqueous liquid components generally take the form of emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates, and oil dispersions.

[0337] Solid compositions are generally in the form of dust, powder, granules, pellets, small particles, soft tablets, tablets, filler films (including powder coatings), and the like, and may be water-dispersible ("wettable") or water-soluble. Films and coatings formed from solutions or flowable suspensions are particularly useful for seed treatment. The active ingredient may be (micro)encapsulated and further formed into a suspension or solid formulation; or, the entire formulation of the active ingredient may be encapsulated (or "coated"). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of emulsifiable concentrate formulations and dry granule formulations. High-strength compositions are primarily used as intermediates for other formulations.

[0338] Aerosol formulations are typically prepared in a suitable medium before spraying. These liquid and solid formulations are formulated to be easily diluted in a spraying medium, typically water, but occasionally another suitable medium such as aromatic or paraffinic hydrocarbons or vegetable oils. Spray volumes can range from about 1 liter per hectare to several thousand liters, but more commonly from about 10 liters to several hundred liters per hectare. Aerosol formulations can be mixed with water or another suitable medium in a container for foliar application via air or ground application, or applied to the plant's growing medium. Liquid and dry formulations can be metered directly into drip systems or into furrows during planting.

[0339] Formulations typically contain effective amounts of active ingredients, diluents, and surfactants within the approximate range described below, totaling up to 100% by weight. weight percentage active Element diluent surfactants Water-dispersible and water-soluble granules, tablets and powders 0.001-90 0-99.999 0-15 Oil dispersions, suspensions, emulsions, and solutions (including emulsifiable concentrates) 1-50 40-99 0-50 dust 1-25 70-99 0-5 Granules and pellets 0.001-99 5-99.999 0-15 High-strength components 90-99 0-10 0-2

[0340] Solid diluents include, for example, clays (such as bentonite, montmorillonite, attapulgite, and kaolin), gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (such as lactose and sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al.'s *Handbook of Insecticide Dust Diluents and Carriers*, 2nd Ed., Dorland Books, Caldwell, New Jersey.

[0341] Liquid diluents include, for example, water, N,N-dimethylalkylamine (such as N,N-dimethylmethamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidone (such as N-methylpyrrolidone), alkyl phosphates (such as triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffin (such as white mineral oil, ortho-paraffin, isoparaffin), alkylbenzene, alkylnaphthalene, glycerol, triacetylglycerol, sorbitol, aromatic hydrocarbons, dearomatic aliphatic hydrocarbons, alkylbenzene, alkylnaphthalene, ketones (such as cyclohexanone, 2-heptanone, isoflavone, and 4-hydroxyl group). 4-Methyl-2-pentanone), acetate esters (such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isocamphenyl acetate), other esters (such as alkyl lactates, diesters, alkyl and aryl benzoates and γ-butyrolactone) and alcohols, which may be straight-chain, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecanol, isooctadecanol, hexadecyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerides of saturated and unsaturated fatty acids (typically C6-C22), such as plant seed and fruit oils (e.g., olive oil, castor oil, linseed oil, sesame oil, corn oil, peanut oil, sunflower oil, grapeseed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, coconut oil, and palm kernel oil), animal fats (e.g., tallow, lard, pork fat, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated), which can be obtained by hydrolysis of glycerides from plant and animal sources and can be purified by distillation. Typical liquid diluents are described in Marsden's Solvents Guide, 2nd edition, Interscience, New York, 1950.

[0342] The solid and liquid compositions of this invention typically include one or more surfactants. When added to a liquid, the surfactant (also known as a "surfactant") typically modifies (most commonly reduces) the surface tension of the liquid. Surfactants can be used as wetting agents, dispersants, emulsifiers, or defoamers, depending on the characteristics of the hydrophilic and lipophilic groups in the surfactant molecule.

[0343] Surfactants can be classified as nonionic, anionic, or cationic. Nonionic surfactants used in this composition include, but are not limited to, alcohol alkoxides, such as alcohol alkoxides based on natural and synthetic alcohols (which may be branched or linear), and prepared from these alcohols and ethylene oxide, propylene oxide, butyl oxide, or mixtures thereof; amine ethoxides, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, such as ethoxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxides, such as octylphenol ethoxide, nonylphenol ethoxide, dinonylphenol ethoxide, and dodecylphenol ethoxide (prepared from phenols and ethylene oxide, propylene oxide, butyl oxide, or mixtures thereof); and block polymers prepared from ethylene oxide or propylene oxide and anti-block polymers. Polymers, wherein the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty acid esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butyl oxide or mixtures thereof); fatty acid esters, glycerides, lanolin-based derivatives, polyethoxylated esters, such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitan fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives, such as sorbitan esters; polymeric surfactants, such as random copolymers, block copolymers, alkyd polyethylene glycol (PEG) resins, grafted or comb polymers and star polymers; polyethylene glycol; polyethylene glycol fatty acid esters; silicone surfactants; and sugar derivatives, such as sucrose esters, alkyl polysaccharides and alkyl polysaccharides.

[0344] Suitable anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohols or alkylphenol ethoxides; diphenyl sulfonate derivatives; lignin and lignin derivatives, such as lignosulfonates; maleic acid or succinic acid or their anhydrides; olefin sulfonates; phosphate esters, such as phosphate esters of alcohol alkoxides, phosphate esters of alkylphenol alkoxides and phosphate esters of styrylphenol ethoxides; protein surfactants; sarcosine derivatives; styrylphenol ether sulfates; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and acetamines, such as N,N-alkyl taurine; sulfonates of benzene, cumene, toluene, xylene and dodecyl and tridecylbenzene; sulfonates of condensed naphthalene; sulfonates of naphthalene and alkylnaphthalene; sulfonates of fractionated petroleum; sulfonated succinates; and sulfonated succinates and their derivatives, such as dialkyl sulfonated succinates.

[0345] Suitable cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines, such as N-alkylpropane diamine, tripropylene triamine and diallyl tetraamine, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butyl oxide, or mixtures thereof); amine salts, such as amine acetates and diamine salts; quaternary ammonium salts, such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides, such as alkyl dimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

[0346] The compositions of this invention may also use mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic, and cationic surfactants and their suggested uses are disclosed in the various published references, including: McCutcheon's Emulsifiers and Detergents, Annual US and International Editions, McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Pub. Co., Inc., New York, 1964; and A.S. Davidson and B. Milwidsky, Synthetic Detergents, 7th Edition, John Wiley and Sons, New York, 1987.

[0347] The compositions of this invention may also include formulation aids and additives known to those skilled in the art (some of which may also function as solid diluents, liquid diluents, or surfactants). Such formulation aids and additives can control: pH (buffers), foaming during processing (defoamers, such as polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), microbial growth within the container (antimicrobials), product freezing (antifreeze agents), color (dye / pigment dispersions), washability (film-forming agents or adhesives), evaporation (evaporation retarders), and other formulation properties. Film-forming agents include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation additives and auxiliaries include those listed below: McCutcheon's Volume 2: Functional Materials, annual international and North American editions, published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT application WO 03 / 024222.

[0348] Mode [1] Compounds and any other active ingredients are typically incorporated into the composition by dissolving the active ingredient in a solvent or by milling in a liquid or dry diluent. Solutions comprising emulsifiable concentrates can be prepared by simply mixing the components. If the solvent intended to be used as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added during dilution with water to emulsify the solvent containing the active ingredient. Active ingredient slurries having particle sizes up to 2,000 μm can be wet-milled using a media mill to obtain particles with an average particle size of less than 3 μm. Aqueous slurries can be prepared into a final suspension concentrate (see, for example, US3,060,084) or further processed by spray drying to form water-dispersible particles. Dry formulations typically require a dry milling process, producing particles with an average particle size ranging from 2 to 10 μm. Dusts and powders can be prepared by blending and typically by milling (e.g., using a hammer mill or a fluid energy mill). Granules and pellets can be prepared by spraying the active material onto a pre-formed granular carrier or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147-48; Perry's Chemical Engineer's Handbook, 4th edition, McGraw-Hill, New York, 1963, pp. 8-57 and below; and WO 91 / 13546. Pellets can be prepared as described in US4,172,714. Water-dispersible and water-soluble particles can be prepared as taught in US4,144,050, US3,920,442, and DE 3,246,493. Tablets can be prepared as taught in US5,180,587, US5,232,701, and US5,208,030. The film-forming agent can be prepared as taught in GB 2,095,558 and US 3,299,566.

[0349] For further information on formulation technology, see T.S. Woods, “The Formulator’s Toolbox - Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T.R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also US 3,235,361, Col. 6, lines 16 to Col. 7, line 19 and Examples 10-41; US ​​3,309,192, Col. 5, lines 43 to Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; US 2,891,855, Col. 3, lines 66 to Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Edition, Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

[0350] In the following examples, all percentages are by weight and all formulations were prepared in a conventional manner. The number of compounds refers to those listed in indexes A through G. Without further explanation, it is believed that those skilled in the art using the foregoing description will fully utilize the scope of the invention. The following examples are therefore considered illustrative only and do not limit the scope of this disclosure in any way. Percentages are by weight unless otherwise specified. Example A High-strength concentrate Compound 260 98.5% Silicon aerogel 0.5% Synthetic amorphous fine silica 1.0% Example B wettable powder Compound 260 65.0% Dodecylphenol polyethylene glycol ether 2.0% Sodium lignosulfonate 4.0% Sodium aluminosilicate 6.0% Montmorillonite (calcined) 23.0% Example C Particles Compound 260 10.0% Magnesium aluminum sepiolite granules (low volatile material, 0.71 / 0.30 mm; USS No. 25-50 sieve) 90.0% Example D Extruded pellets Compound 260 25.0% Anhydrous sodium sulfate 10.0% Crude calcium lignosulfonate 5.0% Sodium alkylnaphthalenesulfonate 1.0% Calcium / Magnesium Bentonite 59.0% Example E Emulsifiable concentrate Compound 260 10.0% Polyoxyethylene sorbitan hexaoleate 20.0% C6-C10 fatty acid methyl esters 70.0% Example F microemulsion Compound 260 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglucosides 30.0% Glyceryl monooleate 15.0% water 20.0% Example G Suspended concentrate Compound 260 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% Based on polysiloxane defoamer 0.1% 1,2-Benzisothiazol-3-one 0.1% water 53.7% Example H emulsion in water Compound 260 10.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol block copolymer 1.0% Styrene-acrylic polymer 1.0% Xanthan Gum 0.1% Propylene glycol 5.0% Based on polysiloxane defoamer 0.1% 1,2-Benzisothiazol-3-one 0.1% Aromatic petroleum hydrocarbons 20.0 water 58.7% Example I oil dispersions Compound 260 25% Polyoxyethylene sorbitan hexaoleate 15% Organic modified bentonite clay 2.5% Fatty acid methyl esters 57.5%

[0351] Additional formulation examples include Examples A to I above, wherein "Compound 260" in each of Examples A to I is replaced by an individual compound in Index Table A as shown below. Compound numbering Compound numbering Compound 16 Compound 197 Compound 6 Compound 121 Compound 18 Compound 120 Compound 128 Compound 267 Compound 190 Compound 140 Compound 207 Compound 159 Compound 103 Compound 100 Compound 268 Compound 324 Compound 330 Compound 329 Compound 289 Compound 336 Compound 331 Compound 325

[0352] Test results indicate that the compounds of this invention are highly active pre- and / or post-emergence herbicides and / or plant growth regulators. The compounds of this invention generally exhibit the highest activity for both post-emergence weed control (i.e., application after weed seedlings have emerged from the soil) and pre-emergence weed control (i.e., application before weed seedlings emerge from the soil). In areas where complete control of all vegetation is desired, such as around fuel storage tanks, industrial storage areas, parking lots, drive-in cinemas, airports, riverbanks, irrigation and other waterways, billboards, and highway and railway facilities, many of these compounds are effective for broad-area pre- and / or post-emergence weed control. Many of the compounds of this invention can be used for selective control of grasses and broadleaf weeds in crop / weed mixed environments by means of selective metabolism in crops and weeds, selective activity at physiological inhibitory sites in crops and weeds, or selective application on or in environments where crops and weeds are mixed. Those skilled in the art will recognize that a preferred combination of selectivity factors among compounds or groups of compounds can be easily determined by performing routine biological and / or biochemical assays. Important agronomic crops that may exhibit tolerance to the compounds of this invention include, but are not limited to, alfalfa, barley, cotton, wheat, rapeseed, sugar beets, corn, sorghum, soybeans, rice, oats, peanuts, vegetables, tomatoes, potatoes, perennial crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, bananas, plantains, pineapples, dried hops, tea, and trees such as eucalyptus and conifers (such as slash pine) and turfgrass species (such as Kentucky bluegrass, St. Augustine grass, Kentucky Fiske grass, and Bermuda grass). The compounds of this invention can be used in crops that have been genetically modified or bred to introduce herbicide resistance, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and / or exhibit other useful traits. Those skilled in the art will understand that not all compounds are equally effective against all weeds. Alternatively, these compounds can be used to improve plant growth.

[0353] Because the compounds of the present invention have both pre- and post-emergence herbicidal activity, they can control unwanted vegetation by killing or poisoning it or reducing its growth. These compounds can be applied usefully by various methods involving contacting a herbicidally effective amount of the compound of the present invention (or a composition comprising the compound and at least one surfactant, solid diluent, or liquid diluent) with the leaves or other parts of the unwanted vegetation or the environment of the unwanted vegetation, such as soil or water in which the unwanted vegetation grows or surrounding the seeds or other propagules of the unwanted vegetation.

[0354] The effective herbicidal amount of the compounds of this invention is determined by considering a variety of factors. These factors include: the selected formulation, the application method, the quantity and type of vegetation present, and the growing conditions. Generally, the effective herbicidal amount of the compounds of this invention is about 0.001 to 20 kg / ha, and a preferred range is about 0.004 to 1 kg / ha. Those skilled in the art can easily determine the effective herbicidal amount required to achieve the desired level of weed control.

[0355] In a common specific embodiment, the compounds of the present invention (typically formulated compositions) are applied to a site containing both desired vegetation (e.g., crops) and non-desired vegetation (i.e., weeds) in contact with a growth medium (e.g., soil), both of which may be seeds, seedlings, and / or larger plants. In this location, compositions containing the compounds of the present invention may be applied directly to the plants or portions thereof (especially non-desired vegetation) and / or to the growth medium in contact with the plants.

[0356] The desired plant species and cultivars in the locations treated with the compounds of this invention can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants (transgenic plants) are those in which a heterologous gene (transgenic gene) has been stably integrated into the plant genome. A transgenic gene defined by its specific location within the plant genome is called a transformation or gene transfer event.

[0357] Genetically modified plant cultivars in the locations where this invention can be applied include those resistant to one or more biotic stresses (pests, such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, cold temperatures, soil salinity, etc.) or containing other desirable characteristics. Plants can be genetically modified to exhibit traits such as herbicide tolerance, insect resistance, altered oil profile, or drought tolerance.

[0358] While the compounds of this invention are most typically used to control unwanted vegetation, contacting the desired vegetation in the treated area with the compounds may result in a super-additive or synergistic effect on the genetic traits of the desired vegetation, including traits introduced through genetic modification. For example, resistance to herbivorous insect pests or plant diseases, tolerance to biotic / abiotic stress, or storage stability may be higher than expected from genetic traits derived from the desired vegetation.

[0359] The compounds of this invention can also be mixed with one or more other bioactive compounds or agents, including herbicides, herbicide safeners, fungicides, insecticides, nematicides, fungicides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemical sterilizers, chemical signaling agents, insect repellents, attractants, pheromones, feeding stimulants, phytonutrients, other bioactive compounds, or entomopathogenic bacteria, viruses, or fungi, to form multi-component insecticides, thereby providing a broader range of agricultural protection. Mixtures of the compounds of this invention with other herbicides can extend the range of activity against additional weed species and suppress the proliferation of any resistant biotypes. Therefore, this invention also relates to compositions comprising a compound of formula 1 (in a herbicidally effective amount) and at least one additional bioactive compound or agent (in a bioactive amount), and may further comprise at least one of a surfactant, a solid diluent, or a liquid diluent. Other bioactive compounds or agents may be formulated into compositions comprising at least one of a surfactant, a solid diluent, or a liquid diluent. For the mixtures of the present invention, one or more other bioactive compounds or agents may be formulated together with the compound of Formula 1 to form a premix, or one or more other bioactive compounds or agents may be formulated separately from the compound of Formula 1 and combined together (e.g., in a spray tank) or applied sequentially before application.

[0360] A mixture of one or more of the following herbicides with the compounds of this invention is particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclolein, 2-propenal, alachlor, alloxydim, ametryn, amicabazone, amidosulfuron, aminocyclopyrachlor and its esters (such as methyl ester, ethyl ester) and salts (such as sodium salt, potassium salt), aminopyralid, amitrol, ammonium sulfonate. sulfamate, ailofos, asulam, atrazine, azimsulfuron, beflubutamid, benzolin, benzolin-ethyl, benzcarbazone, benzfluralin, benzuresate, benzsulfuron-methyl, benzulide, benzalkonium chloride, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate octanoate), butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cefenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon.Chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl gyl), cromazine, cromazine, cromazine, cromazine-olamine, cromazine-sulfuron, cromazine-sulfuron, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and butotyl ester), butyl ester, isoctyl ester and isopropyl ester and their dimethylammonium salts, diolamine salts and triethanolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium salts, potassium salts and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium salts, dimethylammonium salts, potassium salts and sodium salts, dichlorobenzenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat sulfate Metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethachlor-P, dimethipinDimethylarsinic acid and its sodium salt, diinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, ethylfenazate... enoxaprop-ethyl), fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl Flazasulfuron, Florasulam, Fluazifop-butyl, Fluazifop-P-butyl, Fluazolate, Flucarbazone, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpyr, Flufenpyr-ethyl, and Zyroxysulfuron Amines (flumetsulam), flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridoneFluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and their salts such as ammonium salts, isopropylammonium salts, potassium salts, sodium salts (including sesquisodium salts) and trimethylsulfonate (also known as sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl haloxyfop-methyl, hexazinone, hydantocidin, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate octanoate), ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactoferrin, lenacil, linuron, maleic hydrazide, MCPA and its salts (such as MCPA-dimethylammonium salt, MCPA-potassium salt and MCPA-sodium salt), esters (such as MCPA-2-ethylhexyl ester, MCPA-butoxyethyl ester) and thioesters (such as MCPA-thioethyl ester).MCPB and its salts (such as MCPB-sodium salt) and esters (such as MCPB-ethyl ester), mecopropionic acid, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid (acid) and its calcium salt, monoammonium salt, monosodium salt and disodium salt, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate. Monolinuron, Naproanilide, Napropamide, Napropamide-M, Naaptalam, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat Dichloride, Pebulate, Pelargonic acid), pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafenPinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxy Carbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, barnyardgrass (p... yributicarb), pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, ethylquizalofop-ethyl Quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfurosulfuron, 2,3,6-TBA, TCA, sodium TCATebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiob Encarb, tiafenacil, tiocarbazil, tolpyralate, toramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, trilopyr, trilopyr-butotyl, tril opyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthidium-2(1H)-one, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexane] [[hexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinolinone, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinemethylamine, 7-(3,5-dichloro-4-pyridyl)-5-(2,2-difluoroethyl)-8-hydroxypyridino[2,3-b]pyridine-6(5H-one), 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridine, 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoazole (formerly methioxolin)]4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-tri-3,5(2H,4H)-dione, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid methyl ester, 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide, and 2-methyl-N-(4-methyl-1,2,5-diazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides also include biological herbicides such as *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.

[0361] The compounds of this invention can also be used in combination with plant growth regulators (such as aviglycine, N-(phenylmethyl)-1H-purine-6-amine, epoccholeone, gibberellic acid, gibberellin A4 and A7, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate, and trinexapac-methyl)) and plant growth modifiers (such as Bacillus cereus strain BP01).

[0362] General references for agricultural protective agents (i.e., herbicides, herbicide safeners, insecticides, fungicides, nematicides, acaricides, and biopesticides) include The Pesticide Manual, 13th Edition, CDS Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2003 and The BioPesticide Manual, 2nd Edition, LG Coping, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2001.

[0363] For specific embodiments using one or more of these various mixed partner agents, the typical dosage of the mixed partner agent is similar to the usual dosage when the mixed partner agent is used alone. More specifically, in the mixture, the active ingredient is typically applied at half to all of the dosage of the active ingredient used alone as specified on the product label. Series of dosages are shown in references such as The Pesticide Manual and The BioPesticide Manual. These various mixed partner agents (total) are used in relation to the formula... [1] The weight ratio of the compounds is generally between about 1:3000 and about 3000:1. It is noteworthy that the weight percentages are between about 1:300 and about 300:1 (e.g., ratios between about 1:30 and about 30:1). Those skilled in the art can easily determine the bioavailable amount of the active ingredient required to achieve the desired range of bioactivity through simple experiments. It will be apparent that including such additional components can expand the range of weed control beyond that achieved by using them alone. [1] The scope of the compound's prevention and control.

[0364] In certain situations, compositions of the compounds of this invention with other bioactive (especially herbicidal) compounds or agents (i.e., active ingredients) can produce a greater than additive (i.e., synergistic) effect against weeds, and / or a less than additive (i.e., safer) effect on crops or other desired plants. Reducing the amount of active ingredient released into the environment while ensuring effective pest control is always ideal. It is also ideal to be able to use larger amounts of active ingredient to provide more effective weed control without causing excessive crop damage. When the herbicidal active ingredient synergizes with weeds at an application rate that achieves agronomically satisfactory weed control, such combinations can advantageously reduce crop production costs and environmental impact. When the saferization of the herbicidal active ingredient occurs on crops, such combinations can advantageously improve crop protection by reducing weed competition.

[0365] It is noteworthy that the compounds of the present invention are combined with at least one other herbicidal active ingredient. Particularly noteworthy combinations are those where the other herbicidal active ingredient has a different site of action than the compound of the present invention. In certain cases, combinations with at least one other herbicidal active ingredient having a similar range of control but a different site of action will be particularly beneficial for resistance management. Therefore, the compositions of the present invention may further comprise at least one additional herbicidal active ingredient (in a herbicidally effective amount) having a similar range of control but a different site of action.

[0366] The compounds of this invention can also be used in combination with herbicide safeners to increase safety for specific crops. These herbicide safeners include: allidochlor, benzoxacor, cloquintocet-mexyl, bensulfuron, cyometrinil, cyprosulfonamide, dichlormid, cyprosulfuron, dietholate, piperazine, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, and naphthalic anhydride. anhydride)(1,8-naphthalene anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetylated)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dichlorobenzene (MG 191), ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-sideoxy-2-phenyl-5-pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxylamine, 3-sideoxy-1-cyclohexen-1-yl-(3,4-dimethylphenyl)-1,6-dihydro-6-sideoxy-2-phenyl-5-pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5-trimethyl-3-azoloalkyl)-acetone, and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzylamine. The effective amount of the herbicide safener can be applied simultaneously with the compounds of this invention or as a seed treatment. Therefore, one aspect of the present invention relates to a herbicide mixture comprising the compound of the present invention and an effective amount of the herbicide safener. Seed treatment is particularly useful for selective weed control because it physically confines the detoxification effect to the crop plant. Therefore, a particularly useful specific embodiment of the present invention is a method for selectively controlling unwanted vegetation growth in crops, comprising contacting the site of the crop with an effective amount of the herbicide compound of the present invention, wherein the seeds growing the crop are treated with an effective amount of the safener.Those skilled in the art can easily determine the effective antidote dosage of this safety agent through simple experiments.

[0367] The compounds of the present invention may also be mixed with the following: (1) polynucleotides that provide herbicidal effects, including but not limited to DNA, RNA and / or chemically modified nucleotides that affect the amount of a specific target by downregulating, interfering with, inhibiting or silencing gene-derived transcripts; or (2) polynucleotides that provide safety effects, including but not limited to DNA, RNA and / or chemically modified nucleotides that affect the amount of a specific target by downregulating, interfering with, inhibiting or silencing gene-derived transcripts.

[0368] It is noteworthy that the composition includes the following: (an effective amount) of the compound of the present invention, (an effective amount) at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

[0369] For better control of unwanted vegetation (e.g., lower utilization rates due to synergistic effects, wider weed control range, or improved crop safety) or prevention of the development of resistant weeds, the compounds of the present invention are preferred in combination with herbicides selected from the group consisting of: atrazine, azimsulfuron, beflubutamid, S-flubutamid, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clonazolone, clopyralid potassium, cloransulam-methyl, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoazolidinone (CA No.). 81777-95-9) and 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoazolidinone (CA No. 81778-66-7), ethametsulfuron-methyl, flumetsulam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-sideoxy-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-tris(2H,4H)-dione, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, and metribuzin. A mixture of metribuzin, metsulfuron-methyl, pethoxamid, picloram, pyroxasulfone, quinclorac, rimsulfuron, rinskor, S-Modo, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl, and tribensulfuron-methyl. Table A1 lists the specific combinations of components (a) and (b) illustrating the mixtures, compositions, and methods of the present invention. The compound # in component (a) column is indicated in Index Table A.The second column of Table A1 lists the compounds of a specific component (b) (such as "2,4-D" in the first row). Columns three, four, and five of Table A1 list the range of weight ratios of component (a) to component (b) (i.e., (a):(b)) when typically applied to field-grown crops. Therefore, for example, the first row of Table A1 specifically reveals that the combination of component (a) (i.e., compound 45 in Index Table A) and 2,4-D is generally applied at a weight ratio between 1:192 and 6:1. The remaining rows of Table A1 are constructed in a similar manner. Table A1 Component (a) (Compound #) Component (b) Typical weight ratio More typical weight ratio The most typical weight ratio 260 2,4-D 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Acetochlor 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Acifluorfen 1:96 - 12:1 1:32 - 4:1 1:12 - 1:2 260 Aclonifen 1:857 - 2:1 1:285 - 1:3 1:107 - 1:12 260 Alachlor 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Ametryn (a herbicide) 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Amicarbazone 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Amidosulfuron 1:6 - 168:1 1:2 - 56:1 1:1 - 11:1 260 Aminocyclopyrachlor 1:48 - 24:1 1:16 - 8:1 1:6 - 2:1 260 Aminopyralid 1:20 - 56:1 1:6 - 19:1 1:2 - 4:1 260 Amitrole (a herbicide) 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Anilofos 1:96 - 12:1 1:32 - 4:1 1:12 - 1:2 260 Asula 1:960 - 2:1 1:320 - 1:3 1:120 - 1:14 260 Atrazine 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Azimsulfuron 1:6 - 168:1 1:2 - 56:1 1:1 - 11:1 260 Beflubutamid 1:342 - 4:1 1:114 - 2:1 1:42 - 1:5 260 Benfuresate 1:617 - 2:1 1:205 - 1:2 1:77 - 1:9 260 Bensulfuron-methyl 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Bentazone 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Benzobicyclone 1:85 - 14:1 1:28 - 5:1 1:10 - 1:2 260 Benzofenap 1:257 - 5:1 1:85 - 2:1 1:32 - 1:4 260 Bicyclopyrone 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Bifenox 1:257 - 5:1 1:85 - 2:1 1:32 - 1:4 260 Bispyribac-sodium 1:10 - 112:1 1:3 - 38:1 1:1 - 7:1 260 Bromacil 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Bromobutide 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Bromophenyl nitrile (Bromoxynil) 1:96 - 12:1 1:32 - 4:1 1:12 - 1:2 260 Butachlor 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Butafenacil 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Butylate (a type of grass used to weed out enemies) 1:1542 - 1:2 1:514 - 1:5 1:192 - 1:22 260 Carfenstrole 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Carfentrazone-ethyl 1:128 - 9:1 1:42 - 3:1 1:16 - 1:2 260 Chlorimuron-ethyl 1:8 - 135:1 1:2 - 45:1 1:1 - 9:1 260 Chlorotoluron 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Chlorsulfuron 1:6 - 168:1 1:2 - 56:1 1:1 - 11:1 260 Cincosulfuron 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Cinidon-ethyl indole-7-ethyl 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Cinmethylin 1:34 - 34:1 1:11 - 12:1 1:4 - 3:1 260 Clacyfos 1:34 - 34:1 1:11 - 12:1 1:4 - 3:1 260 Clethodim 1:48 - 24:1 1:16 - 8:1 1:6 - 2:1 260 Clodinafop-propargyl 1:20 - 56:1 1:6 - 19:1 1:2 - 4:1 260 Clomazone 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Clomeprop 1:171 - 7:1 1:57 - 3:1 1:21 - 1:3 260 Clopyralid 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Cloransulam-methyl 1:12 - 96:1 1:4 - 32:1 1:1 - 6:1 260 Cumyluron 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Cyanazine 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Cyclopyrimorate 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Cyclosulfamuron 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Cycloxydim 1:96 - 12:1 1:32 - 4:1 1:12 - 1:2 260 Cyhalofop 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Daimuron 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Desmedipham (Beetroot Anne) 1:322 - 4:1 1:107 - 2:1 1:40 - 1:5 260 Dicamba 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Dichlorobenzonitrile (Dichlobenil) 1:1371 - 1:2 1:457 - 1:4 1:171 - 1:20 260 Dichlorprop 1:925 - 2:1 1:308 - 1:3 1:115 - 1:13 260 Diclofop-methyl 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Diclosulam 1:10 - 112:1 1:3 - 38:1 1:1 - 7:1 260 Difenzoquat 1:288 - 4:1 1:96 - 2:1 1:36 - 1:4 260 Diflufenican 1:857 - 2:1 1:285 - 1:3 1:107 - 1:12 260 Diflufenzopyr 1:12 - 96:1 1:4 - 32:1 1:1 - 6:1 260 Dimethachlor 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Dimethametryn 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Dimethenamid-P 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Dithiopyr 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Diuron 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 EPTC 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Esprocarb 1:1371 - 1:2 1:457 - 1:4 1:171 - 1:20 260 Ethalfluralin 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Ethametsulfuron-methyl 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Ethoxyfen 1:8 - 135:1 1:2 - 45:1 1:1 - 9:1 260 Ethoxysulfuron 1:20 - 56:1 1:6 - 19:1 1:2 - 4:1 260 Etobenzanid 1:257 - 5:1 1:85 - 2:1 1:32 - 1:4 260 Fenoxaprop-ethyl 1:120 - 10:1 1:40 - 4:1 1:15 - 1:2 260 Fenoxasulfone 1:85 - 14:1 1:28 - 5:1 1:10 - 1:2 260 Fenquinotrione 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Fentrazamide 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Flazasulfuron 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Florasulam 1:2 - 420:1 1:1 - 140:1 2:1 - 27:1 260 Fluazifop-butyl 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Flucarbazone 1:8 - 135:1 1:2 - 45:1 1:1 - 9:1 260 Flucetosulfuron 1:8 - 135:1 1:2 - 45:1 1:1 - 9:1 260 Flufenacet 1:257 - 5:1 1:85 - 2:1 1:32 - 1:4 260 Flumetsulam 1:24 - 48:1 1:8 - 16:1 1:3 - 3:1 260 Fluocinolone acetonide (Flumiclorac-pentyl) 1:10 - 112:1 1:3 - 38:1 1:1 - 7:1 260 Flumioxazin 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Fluometuron 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Flupyrsulfuron-methyl 1:3 - 336:1 1:1 - 112:1 2:1 - 21:1 260 Fluridone 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Fluoroxypyr 1:96 - 12:1 1:32 - 4:1 1:12 - 1:2 260 Flurtamone 1:857 - 2:1 1:285 - 1:3 1:107 - 1:12 260 Fluthiacet-methyl 1:48 - 42:1 1:16 - 14:1 1:3 - 3:1 260 Fomesafen (a flumetsulam herbicide) 1:96 - 12:1 1:32 - 4:1 1:12 - 1:2 260 Foramsulfuron 1:13 - 84:1 1:4 - 28:1 1:1 - 6:1 260 Glufosinate 1:288 - 4:1 1:96 - 2:1 1:36 - 1:4 260 Glyphosate 1:288 - 4:1 1:96 - 2:1 1:36 - 1:4 260 Halosulfuron-methyl 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Halauxifen 1:20 - 56:1 1:6 - 19:1 1:2 - 4:1 260 Halauxifen methyl 1:20 - 56:1 1:6 - 19:1 1:2 - 4:1 260 Haloxyfop-methyl 1:34 - 34:1 1:11 - 12:1 1:4 - 3:1 260 Hexazinone 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Hydantocidin 1:1100 - 16:1 1:385 - 8:1 1:144 - 4:1 260 Imazamox 1:13 - 84:1 1:4 - 28:1 1:1 - 6:1 260 Imazapic (a type of nicotinic acid) 1:20 - 56:1 1:6 - 19:1 1:2 - 4:1 260 Imazapyr 1:85 - 14:1 1:28 - 5:1 1:10 - 1:2 260 Imazaquin 1:34 - 34:1 1:11 - 12:1 1:4 - 3:1 260 Imazethabenz-methyl 1:171 - 7:1 1:57 - 3:1 1:21 - 1:3 260 Imazethapyr (a type of tobacco product) 1:24 - 48:1 1:8 - 16:1 1:3 - 3:1 260 Imazosulfuron 1:27 - 42:1 1:9 - 14:1 1:3 - 3:1 260 Indanofan 1:342 - 4:1 1:114 - 2:1 1:42 - 1:5 260 Indaziflam 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Iodosulfuron-methyl 1:3 - 336:1 1:1 - 112:1 2:1 - 21:1 260 Ioxynil 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Ipfencarbazone 1:85 - 14:1 1:28 - 5:1 1:10 - 1:2 260 Isoproturon 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Isoxaben 1:288 - 4:1 1:96 - 2:1 1:36 - 1:4 260 Isoxaflutole 1:60 - 20:1 1:20 - 7:1 1:7 - 2:1 260 Lactofen 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Lenacin 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Linuron 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 MCPA 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 MCPB 1:288 - 4:1 1:96 - 2:1 1:36 - 1:4 260 Mecopropionic acid 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Mefenacet 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Mefluidide 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Mesosulfuron-methyl 1:5 - 224:1 1:1 - 75:1 1:1 - 14:1 260 Mesotrione 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Metamifop 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Metazachlor 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Metazosulfuron 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Methabenzthiazuron 1:768 - 2:1 1:256 - 1:2<00X4567> 1:96 - 1:11 260 Metolachlor 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Metosulam 1:8 - 135:1 1:2 - 45:1 1:1 - 9:1 260 Metribuzin 1:192 - 6:1 1:X4 - 2:1 1:24 - 1:3 260 Metsulfuron-methyl 1:2 - 560:1 1:1 - 187:1 3:1 - 35:1 260 Molinate 1:1028 - 2:1 1:342 - 1:3 1:128 - 1:15 260 Napropamide 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 It should be noted that there is an "X" in the translation of item 47 which might be a typo in the original text. If possible, it is recommended to double-check the original content for accuracy. Napropamide-M (M) 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Naptalam (sodium nitrate) 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Nicosulfuron 1:12 - 96:1 1:4 - 32:1 1:1 - 6:1 260 Norflurazon 1:1152 - 1:1 1:384 - 1:3 1:144 - 1:16 260 Orbencarb 1:1371 - 1:2 1:457 - 1:4 1:171 - 1:20 260 Orthosulfamuron 1:20 - 56:1 1:6 - 19:1 1:2 - 4:1 260 Oryzalin 1:514 - 3:1 1:171 - 1:2 1:64 - 1:8 260 Oxadiargyl 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Oxadiazon 1:548 - 3:1 1:182 - 1:2 1:68 - 1:8 260 Oxasulfuron 1:27 - 42:1 1:9 - 14:1 1:3 - 3:1 260 Oxaziclomefone 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Oxyfluorfen 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Paraquat 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Pendimethalin 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Penoxsulam (a type of rotten shred) 1:10 - 112:1 1:3 - 38:1 1:1 - 7:1 260 Penthoxamid 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Pentoxazone 1:102 - 12:1 1:34 - 4:1 1:12 - 1:2 260 Phenmedipham (beetroot) 1:102 - 12:1 1:34 - 4:1 1:12 - 1:2 260 Picloram 1:96 - 12:1 1:32 - 4:1 1:12 - 1:2 260 Picolinafen 1:34 - 34:1 1:11 - 12:1 1:4 - 3:1 260 Pinoxaden 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Pretilachlor 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Primisulfuron-methyl 1:8 - 135:1 1:2 - 45:1 1:1 - 9:1 260 Prodiamine 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Profoxydim 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Prometryn (a type of herbicide) 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Propachlor 1:1152 - 1:1 1:384 - 1:3 1:144 - 1:16 260 Propanil (weed killer) 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Propaquizafop 1:48 - 24:1 1:16 - 8:1 1:6 - 2:1 260 Propoxycarbazone 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Propyrisulfuron 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Propyzamide 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Prosulfocarb 1:1200 - 1:2 1:400 - 1:4 1:150 - 1:17 260 Prosulfuron 1:6 - 168:1 1:2 - 56:1 1:1 - 11:1 260 Pyraclonil 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Pyraflufen-ethyl 1:5 - 224:1 1:1 - 75:1 1:1 - 14:1 260 Pyrasulfotole 1:13 - 84:1 1:4 - 28:1 1:1 - 6:1 260 Pyrazolynate 1:857 - 2:1 1:285 - 1:3 1:107 - 1:12 260 Pyrazosulfuron-ethyl 1:10 - 112:1 1:3 - 38:1 1:1 - 7:1 260 Pyrazoxyfen 1:5 - 224:1 1:1 - 75:1 1:1 - 14:1 260 Pyribenzoxim 1:10 - 112:1 1:3 - 38:1 1:1 - 7:1 260 Pyributicarb 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Pyridate 1:288 - 4:1 1:96 - 2:1 1:36 - 1:4 260 Pyriftalid 1:10 - 112:1 1:3 - 38:1 1:1 - 7:1 260 Pyriminobac-methyl 1:20 - 56:1 1:6 - 19:1 1:2 - 4:1 260 Pyrimisulfan 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Pyrithiobac 1:24 - 48:1 1:8 - 16:1 1:3 - 3:1 260 Pyroxasulfone 1:85 - 14:1 1:28 - 5:1 1:10 - 1:2 260 Pyroxsulam 1:5 - 224:1 1:1 - 75:1 1:1 - 14:1 260 Quinclorac 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Quizalofop-ethyl 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Rimsulfuron 1:13 - 84:1 1:4 - 28:1 1:1 - 6:1 260 Saflufenacil 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Sethoxydim 1:96 - 12:1 1:32 - 4:1 1:12 - 1:2 260 Simazine 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Sulcotrione 1:120 - 10:1 1:40 - 4:1 1:15 - 1:2 260 Sulfentrazone 1:147 - 8:1 1:49 - 3:1 1:18 - 1:3 260 Sulfometuron-methyl 1:34 - 34:1 1:11 - 12:1 1:4 - 3:1 260 Sulfosulfuron 1:8 - 135:1 1:2 - 45:1 1:1 - 9:1 260 Tebuthiuron 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Tefrostigmine (Tefuryltrione) 1:42 - 27:1 1:14 - 9:1 1:5 - 2:1 260 Tembotrione 1:31 - 37:1 1:10 - 13:1 1:3 - 3:1 260 Teproxydim 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Terbacil 1:288 - 4:1 1:96 - 2:1 1:36 - 1:4 260 Terbuthylazine 1:857 - 2:1 1:285 - 1:3 1:107 - 1:12 260 Terbutryn (a herbicide) 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Thenylchlor 1:85 - 14:1 1:28 - 5:1 1:10 - 1:2 260 Thiazopyr 1:384 - 3:1 1:128 - 1:1 1:48 - 1:6 260 Thiencarbazone 1:3 - 336:1 1:1 - 112:1 2:1 - 21:1 260 Thifensulfuron-methyl 1:5 - 224:1 1:1 - 75:1 1:1 - 14:1 260 Tiafenacil 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Thiobencarb 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Tolpyralate 1:31 - 37:1 1:10 - 13:1 1:3 - 3:1 260 Topramzone 1:6 - 168:1 1:2 - 56:1 1:1 - 11:1 260 Tralkoxydim 1:68 - 17:1 1:22 - 6:1 1:8 - 2:1 260 Triafamone 1:2 - 420:1 1:1 - 140:1 2:1 - 27:1 260 Triallate 1:768 - 2:1 1:256 - 1:2 1:96 - 1:11 260 Triasulfuron 1:5 - 224:1 1:1 - 75:1 1:1 - 14:1 260 Triaziflam 1:171 - 7:1 1:57 - 3:1 1:21 - 1:3 260 Tribenuron-methyl 1:3 - 336:1 1:1 - 112:1 2:1 - 21:1 260 Triclopyr 1:192 - 6:1 1:64 - 2:1 1:24 - 1:3 260 Trifloxysulfuron 1:2 - 420:1 1:1 - 140:1 2:1 - 27:1 260 Trifludimoxazin 1:25 - 45:1 1:8 - 15:1 1:3 - 3:1 260 Trifluralin 1:288 - 4:1 1:96 - 2:1 1:36 - 1:4 260 Triflusulfuron-methyl 1:17 - 68:1 1:5 - 23:1 1:2 - 5:1 260 Tritosulfuron 1:13 - 84:1 1:4 - 28:1 1:1 - 6:1

[0370] Table A2 is constructed in the same manner as Table A1 above, except that the items below the "Component (a) (Compound #)" column heading are replaced with the individual Component (a) column items shown below. Compound 16 in the Component (a) column is indicated in Index Table A. Therefore, for example, in Table A2, all items below the "Component (a)" column heading describe "Compound 16" (i.e., Compound 16 indicated in Index Table A), and the first row below the column heading in Table A2 specifically reveals the mixture of Compound 16 and 2,4-D. Tables A3 to A16 are constructed in a similar manner. Form Number Component (a) column items A2 16 A3 6 A4 18 A5 128 A6 190 A7 207 A8 103 A9 268 A10 197 A11 121 A12 120 A13 267 A14 140 A15 159 A16 100

[0371] The following tests confirm the efficacy of the compounds of this invention against specific weeds. However, the weed control provided by these compounds is not limited to those species. See Indexes A through G for compound descriptions. The following abbreviations are used in the indexes below: "t" for tertiary, "s" for secondary, "n" for n-, "i" for iso, "c" for cyclic, "Me" for methyl, "Et" for ethyl, "Pr" for propyl, "i-Pr" for isopropyl, "Bu" for butyl, "c-Pr" for cyclopropyl, "t-Bu" for tertiary butyl, "Ph" for phenyl, "OMe" for methoxy, "OEt" for ethoxy, "SMe" for methylthio, "SEt" for ethylthio, "-CN" for cyano, "-NO2" for nitro, "TMS" for trimethylalkyl, and "naphthyl" for naphthyl. (R) or (S) indicates the absolute chirality of the asymmetric carbon center. The abbreviation "(d)" indicates that the compound appears to decompose upon melting. The abbreviation "Cmpd. #" represents the "compound number". The abbreviation "Ex." indicates "Example", and the following number indicates that the compound was prepared in that example. Mass spectrometry is recorded as the molecular weight of the highest isotopic abundance precursor ion (M+1) with an estimated accuracy within ±0.5 Da, which is formed by adding H+ (molecular weight 1) to the molecule and is observed using atmospheric pressure chemical ionization (AP+). Index Table A G is CONR5R6; and NR5R6 is J or K. Compound # R1 R2 R3 R4 J or K@ MS MP (°C) 1 Cl H CH3 H J-1 401 2 Cl CH3 H H J-2 415 3 CH3 H CH3 H J-7 411 4 CF3 H H SO2CF3 J-6 497 5 CH3 H CH3 SO2CF3 J-33 515 6 CH3 H CH3 H J-4 367 7 CH3 H H H J-15 182-186 8 CH3 H CH3 H J-12 383 9 CH3 H CH3 H J-3 395 10 CH3 H CH3 H J-28 380 11 CH3 H CH3 H J-10 390 12 CH3 H CH3 H J-33 383 13 Cyclopropyl H CH3 H J-4 393 14 Br H CH3 H J-4 432 15 Cl H H H J-4 373 16 Cl H CH3 H J-4 387 17 Cl H CH3 H J-10 410 18 Cl H CH3 H J-6 385 19 CH3 H CH3 H J-9 395 20 Cl H CH3 H J-3 415 21 Cl H CH3 H K-2 373 22 Cl H CH3 H K-11 373 23 Cl H CH3 H K-1 345 24 Cl H CH3 H J-4 519 25 Cl H CH3 H J-6 517 26 Cl H CH3 H J-33 403 50 CH3 H CH3 H J-46 423 86 CH3 H CH3 H J-8(S) 395 87 CH3 H CH3 H J-35 541 88 CH3 F CH3 H J-35 545 89 CH3 H CH3 SO2CF3 J-32 499 90 CH3 H CH3 SO2CF3 J-7 543 91 CH3 H CH3 C(O)-isopropyl- J-8 465 92 CH3 H CH3 CH2OCO-isopropyl J-8 509 93 CH3 H CH3 COCH3 J-8 437 94 CH3 H CH3 H J-8(R) 395 95 CH3 H CH3 SO2CF3 J-8(R) 527 96 CH3 H CH3 CH2OCOCH3 J-8 467 97 CH3 H CH3 SO2CF3 K-12 482 98 CH3 F CH3 H J-8 413 101 CH3 H CH3 H J-47 425 105 Cl H CH3 H K-12 369 107 CH3 H CH3 H K-7 365 109 CH3 F CH3 H J-12 250-254 110 CH3 F CH3 H J-9 194-198 111 CH3 H CH3 H J-32 367 112 CH3 H CH3 H J-36 381 113 CH3 H CH3 H J-43 381 115 CH3 H CH3 COOMe J-8 453 116 CH3 F CH3 H J-3 175-179 117 CH3 H CH3 SO2CF3 J-8(S) 527 118 CH3 H CH3 SO2CF3 J-14 515 119 CH3 H CH3 SO2CF3 J-8 527 124 CN H CH3 H J-6 379 126 CH3 H CN H J-6 346-349 128 CH3 F CH3 H K-1 243-245 129 CH3 F CH3 H J-41 218-222 130 Cl H CH3 SO2CF3 K-12 501 132 CF3 H CH3 H K-1 202-204 133 CH3 H CF3 H K-1 206-211 134 CH3 H CN H K-1 230-233 137 CH3 H CH3 H J-35 409 138 CH3 H CH3 SO2CF3 J-43 513 141 CH3 H CH3 H K-13 351 142 CH3 H CH3 SO2CF3 K-13 483 145 CH3 H CH3 H K-12 350 146 Cl H CH3 H J-8 415 147 CH3 F CH3 SO2CF3 K-5 499 153 Cl H CH3 H J-5 415 154 CH3 H CH3 H J-25 409 155 CH3 H CH3 H J-14 383 160 CH3 H CH3 H J-34 381 161 CH3 H CH3 SO2CF3 J-10 521 162 CH3 H CH3 H J-10 389 165 CF3 H CH3 H J-6 105-108 169 CH3 H CH3 SO2CF3 K-7 497 174 CH3 F CH3 SO2CF3 J-4 517 175 CH3 H CH3 H J-8 395 179 CH3 F CH3 H K-5 367 180 CH3 H CF3 H J-6 211-214 181 CH3 H CH3 SO2CF3 K-6 505 182 CH3 H CH3 SO2CF3 K-14 467 187 CH3 H CH3 H K-6 373 188 CH3 H CH3 H K-2 353 189 CH3 H CH3 H K-5 349 190 CH3 F CH3 H J-4 236-240 191 CH3 F CH3 H J-6 263-267 192 CH3 H CH3 H K-14 335 193 Cl H CH3 H J-41 443 194 CH3 H CH3 H J-41 437 195 CH3 H CH3 H J-37 433 199 Cl H CH3 H J-48 429 200 Cl H CH3 SO2CF3 J-13 551 201 Cl H CH3 H J-12 403 202 CH3 H CH3 H J-49 387 205 Cl H CH3 SO2CF3 J-41 575 210 CH3 H CH3 SO2CF3 J-23 533 211 CH3 H F H J-6 369 212 CH3 H F SO2CF3 J-6 501 213 CH3 H F H J-4 387 214 CH3 H F SO2CF3 J-4 519 215 CH3 H F H K-1 329 216 CH3 H F SO2CF3 K-1 461 223 CH3 H CH3 H J-38 419 224 Cl H CH3 H J-13 419 225 CH3 H CH3 H J-39 405 229 Cl H CH3 H J-23 421 230 CH3 H CH3 H J-48 409 231 CH3 H CH3 H J-41 423 232 CH3 H CH3 SO2CF3 J-41 555 233 CH3 H CH3 H J-20 443 234 CH3 H CH3 H J-17 448 235 CH3 H F SO2CF3 J-3 531 236 CH3 H F H J-10 394 237 CH3 H F SO2CF3 J-4 503 238 CH3 H F H J-3 399 239 CH3 H F SO2CF3 J-10 526 240 CH3 H F H J-4 371 241 CH3 H CH3 H J-23 401 242 CH3 H CH3 H J-13 399 243 CH3 H CH3 SO2CF3 J-13 531 244 F F CH3 SO2CF3 J-4 389 245 Cl H CH3 H J-50 401 246 Cl H CH3 H J-9 415 247 CH3 H Cl SO2CF3 K-11 505 248 CH3 H Cl H J-4 387 249 CH3 H Cl H K-15 373 250 CH3 H Cl SO2CF3 J-4 519 251 CH3 H Cl H K-1 345 252 CH3 H Cl H J-6 387 253 CH3 H Cl SO2CF3 J-6 517 254 CH3 H Cl H J-4 403 255 CH3 H Cl SO2CF3 J-4 535 256 CH3 H Cl SO2CF3 K-1 477 257 CH3 H Cl H K-11 373 258 Cl H OMe H J-4 212-216 259 CH3 H H H J-6 213-217 260 CH3 H CH3 H J-6 262-266 261 CH3 H CH3 H J-51 244-247 262 CH3 H H H J-51 173-177 263 CH3 H H H J-16 187-191 264 CH3 H CH3 H J-15 228-232 276 CH3 H CH3 SO2CF3 J-34 513 283 CH3 CH3 CH3 H J-33 397 284 CH3 CH3 CH3 H J-53 429 285 CH3 CH3 CH3 CH2OCO-tert-butyl J-33 511 286 CH3 CH3 CH3 CO2Et J-33 469 287 CH3 Cl CH3 H K-1 287 - 290 288 CH3 CH3 CH3 H K-1 259 - 262 289 CH3 CH3 CH3 H J-4 247 - 250 290 CH3 Cl CH3 H J-4 213 - 216 320 Cl F CH3 H K-1 200 - 203 321 Cl F CH3 H J-4 266 - 269 324 CH3 CH3 CH3 CH2OCO-tert-butyl J-4 495 325 CH3 CH3 CH3 CO2Et J-4 453 326 CH3 CH3 CH3 H J-6 379 327 CH3 CH3 CH3 H J-3a 409 328 CH3 CH3 CH3 ​​J-3b 409 329 CH3 CH3 CH3 CH2OCO-tert-butyl J-6 493 330 CH3 CH3 CH3 CO2Et J-6 451 331 CH3 CH3 CH3 CH2OCO-tert-butyl J-3a 523 332 CH3 CH3 CH3 CO2Et J-3a 481 333 Cl F CH3 H J-6 315-318 334 Cl F CH3 H J-8 72-75 337 Cl F CH3 H K-5 189-192 350 CH3 H CH3 CH2OCO-tert-butyl J-23 515 351 CH3 H CH3 CO2Et J-23 473 353 CH3 H CH3 CH2OCO-tert-butyl J-15 493 354 CH3 H CH3 CO2Et J-15 451 356 CH3 CH3 CH3 H J-13 413 357 CH3 CH3 CH3 H J-23 415 358 CH3 CH3 CH3 H J-12 397 359 CH3 CH3 CH3 CH2OCO-tert-butyl J-13 527 360 CH3 CH3 CH3 CH2OCO-tert-butyl J-23 529 361 CH3 CH3 CH3 CH2OCO-tert-butyl J-12 511 362 CH3 H CH3 CH2OCO-tert-butyl J-4 481 363 CH3 H CH3 CO2Et J-4 439 364 CH3 H CH3 CH2OCO-tert-butyl J-54 555 365 CH3 H CH3 CO2Et J-54 513 366 CH3 CH3 CH3 H J-15 393 367 CH3 CH3 CH3 H J-9 409 368 CH3 CH3 CH3 H K-5 363 369 CH3 CH3 CH3 CH2OCO-tert-butyl J-15 507 370 CH3 CH3 CH3 CH2OCO-tert-butyl J-9 523 371 CH3 CH3 CH3 CH2OCO-tert-butyl K-5 477 373 CH3 CH3 CH3 CH2OCO-tert-butyl J-3b 523 374 CH3 CH3 CH3 CO2Et J-3b 481 @See lists 1 and 2, J-1 to J-52 and K-1 to K-9. Index Table B Compound # R1 R2 R3 R4 G-1 MS MP (°C) 99 CH3 H CH3 SO2CF3 G-1-1 121-125 100 CH3 H CH3 CH2OCO-tert-butyl G-1-1a 477 102 CH3 H CH3 CH2OCOMe G-1-1a 435 103 CH3 H CH3 H G-1-1a 363 104 CH3 H CH3 H G-1-2 411 108 CH3 H CH3 H G-1-3 79-82 114 CH3 H CH3 SO2CF3 G-1-4 541 120 CH3 H CH3 H G-1-5 379 121 CH3 H CH3 H G-1-6 117-120 122 CH3 H CH3 H G-1-7 170-173 123 CH3 H CH3 H G-1-8aa 377 125 CH3 H CH3 H G-1-8a 158-161 127 CH3 H CH3 SO2CF3 G-1-3 511 131 CH3 H CH3 H G-1-8 166-169 135 CH3 H CH3 H G-1-9 449 136 CH3 H CH3 SO2CF3 G-1-9 581 139 CH3 H CH3 SO2CF3 G-1-10 551 140 CH3 H CH3 CH2OCO-tert-butyl G-1-11 491 143 CH3 H CH3 CH2OCO-n-Butyl G-1-11 491 144 CH3 H CH3 CH2OCOEt G-1-11 463 148 CH3 H CH3 CH2OCO-cyclohexyl G-1-11 517 149 CH3 H CH3 CH2OCOPh G-1-11 511 150 CH3 H CH3 CH2OCO-cyclopentyl G-1-11 503 151 CH3 H CH3 CH2OCO-Secondary Butyl G-1-11 491 152 CH3 H CH3 CH2OCO-Isobutyl G-1-11 491 158 CH3 H CH3 SO2CF3 G-1-12 537 159 CH3 H CH3 CH2OCO-tert-butyl G-1-13 505 163 CH3 H CH3 H G-1-14 419 164 CH3 H CH3 H G-1-1ab 105 - 108 166 CH3 H CH3 H G-1-1aa 109 - 111 167* CH3 H CH3 H G-1-15 140 - 143 168* CH3 H CH3 H G-1-15 164 - 167 170 CH3 H CH3 H G-1-15 406 171* CH3 H CH3 H G-1-17* 136-140 172 CH3 H CH3 H G-1-19 148-152 173* CH3 H CH3 H G-1-17* 168-171 176 CH3 H CH3 H G-1-4 409 177 CH3 H CH3 H G-1-18 393 178 CH3 H CH3 SO2CF3 G-1-18 525 183 CH3 H Cl H G-1-20 371 184 CH3 H Cl SO2CF3 G-1-20 504 185 CH3 H Cl H G-1-11 397 186 CH3 H Cl SO2CF3 G-1-11 530 196 CH3 H CH3 SO2CF3 G-1-21 495 197 CH3 H CH3 H G-1-13 391 198 CH3 H CH3 SO2CF3 G-1-13 523 203 Cl H CH3 H G-1-20 371 204 Cl H CH3 H G-1-11 397 206 CH3 H CH3 H G-1-20 351 207 CH3 H CH3 H G-1-11 377 208 CH3 H CH3 SO2CF3 G-1-11 509 209 CH3 H CH3 H G-1-22 379 217 Cl H CH3 SO2CF3 G-1-13 543 218 CH3 H CH3 CH2OCOMe G-1-11 449 219 CH3 H CH3 COSMe G-1-11 451 220 CH3 H CH3 COMe G-1-11 419 221 Cl H CH3 H G-1-13 411 222 Cl H CH3 SO2CF3 G-1-20 503 226 CH3 H CH3 H G-1-23 385 227 CH3 H CH3 SO2CF3 G-1-23 517 228 CH3 H CH3 H G-1-21 363 277 CH3 H CH3 H G-1-12 405 291 CH3 H CH3 SO2CF3 G-1-28a 523 292 CH3 H CH3 H G-1-28a 391 293 CH3 H CH3 CH2OCO-tert-butyl G-1-28a** 491 294 CH3 H CH3 CH2OCO-tert-butyl G-1-28a** 505 295 CH3 H CH3 CO2-Isopropyl G-1-1a 449 296 CH3 H CH3 SO2CF3 G-1-24a 497 297 CH3 H CH3 H G-1-24a 365 298 CH3 H CH3 CO2Et G-1-1a 365 299 CH3 H CH3 CO2-Isobutyl G-1-1a 463 300 CH3 H CH3 CO2-n-propyl G-1-1a 463 301 CH3 H CH3 CH2OCO-tert-butyl G-1-24a 479 302 CH3 H Br H G-1-1a 160-163 303 F H CH3 H G-1-11 115-118 304 OMe H CH3 H G-1-11 393 305 CH3 H Et H G-1-1a 146-149 306 CH3 H CF3 H G-1-1a 162v165 307 CH3 H Cyclopropyl H G-1-1a 165-168 308 CH3 H CH3 CH2OCO-Isopropyl G-1-1a 463 309 Br H CH3 H G-1-11 150-153 310 CH3 H F H G-1-1a 135-138 311 Et H CH3 H G-1-11 152-155 312 CH3 H OMe H G-1-1a 178-181 313 Cyclopropyl H CH3 H G-1-11 403 314 CH3 H CH3 CH2OCOO-Isopropyl G-1-1a 479 315 CH3 H CH3 CH2OCOOMe G-1-1a 451 316 CH3 H CH3 CH2OCOO-tertiary butyl G-1-1a 493 317 CH3 H CH3 CH2OCONMe2 G-1-1a 464 318 CH3 H CH3 H G-1-29 367 319 CH3 H CH3 H G-1-30 367 322 CH3 H CH3 H G-1-31 395 323 CH3 H CH3 H G-1-32 395 335 CH3 CH3 CH3 H G-1-1a 377 336 CH3 CH3 CH3 CH2OCO-tert-butyl G-1-1a 491 338 CH3 H CH3 CH2OCO-tert-butyl G-1-30 481 339 CH3 H CH3 CH2OCO-tert-butyl G-1-29 481 340 CH3 H CH3 H G-1-38a 377 341 CH3 H CH3 CH2OCO-tert-butyl G-1-38a 491 342 CH3 H CH3 CH2OCOO-tertiary butyl G-1-38a 493 343 CH3 H CH3 H G-1-33a 379 344 CH3 H CH3 CH2OCO-tert-butyl G-1-33a 493 345 CH3 H CH3 CO2-Isobutyl G-1-33a 479 346 CH3 H CH3 H G-1-33b 379 347 CH3 H CH3 CH2OCO-tert-butyl G-1-33b 493 348 CH3 H CH3 CO2-Isobutyl G-1-33b 479 349 CH3 H CH3 H G-1-34a 365 352 CH3 H CH3 CH2OCO-tert-butyl G-1-34a 479 355 CH3 H Cyclopropyl CH2OCO-tert-butyl G-1-1a 503 372 CH3 H CH3 H G-1-35a 379 375 CH3 H CH3 H G-1-36 351 376 CH3 H CH3 CH2OCO-tert-butyl G-1-36 465 377 CH3 H H H G-1-1a 349 378 CH3 H Et CH2OCO-tert-butyl G-1-1a 491 379 CH3 H Et CO2Et G-1-1a 449 380 CH3 CH3 CH3 H G-1-11 391 381 CH3 H CH3 H G-1-37 365 382 CH3 CH3 CH3 CH2OCO-tert-butyl G-1-11 505 383 CH3 H CH3 CH2OCO-tert-butyl G-1-37 479 384 CH3 H n-Propyl H G-1-1a 391 385 CH3 H n-Propyl CH2OCO-tert-butyl G-1-1a 505 386 CH3 CH3 CH3 CH2OCO-tert-butyl G-1-33b 507 387 CH3 CH3 CH3 H G-1-24a 379 388 CH3 CH3 CH3 H G-1-34a 379 389 CH3 CH3 CH3 CH2OCO-tert-butyl G-1-24a 493 390 CH3 CH3 CH3 CH2OCO-tert-butyl G-1-34a 493 391 CH3 CH3 CH3 CH2OCO-tert-butyl G-1-33a 507 See List 3, G-1-1 to G-1-27. * indicates a trans or cis isomer of the compound associated with two methyl groups on a six-membered ring. ** indicates that the compound is a mirror isomer. Index Table C Compound # R1 R2 R3 R4 G-2 MS 156 CH3 H CH3 H G-2-1 409 157 CH3 H CH3 SO2CF3 G-2-1 ** 265 CH3 H CH3 COMe G-2-2 447 266 CH3 H CH3 COOMe G-2-2 463 267 CH3 H CH3 SO2CF3 G-2-2 537 268 CH3 H CH3 CH2OCO-tert-butyl G-2-2 519 269 CH3 H CH3 SO2CF3 G-2-3 539 270 CH3 H CH3 H G-2-4 391 273 Cl H D CH3 H G-2-4 411 274 CH3 H CH3 H D G-2-5 393 275 CH3 H CH3 SO2CF3 G-2-5 ** 278 CH3 [[ID=)93]] H CH3 H G-2-2 405 279 CH3 D H Note: There seems to be a "D" added in some lines in the translated text which might be a mistake in the original text or an unclear instruction. Please double-check the source for accuracy.CH3 H G-2-3 407 280 CH3 H CH3 SO2CF3 G-2-4 523 392 CH3 H CH3 H G-2-13 405 393 Cl H CH3 H G-2-2 425 394 Cl H CH3 H G-2-3 427 395 CH3 H CH3 SO2CF3 G-2-14 573 396 CH3 H CH3 H[[ID=9⑶ G-2-14 441 397 CH3 H CH3 CH2OCO-tert-butyl G-2-14 555 398 CH3 H CH3 H G-2-15 212-215 399 CH3 H CH3 SO2CF3 G-2-16 605 400 CH3 H CH3 H G-2-16 473 401 CH3 H CH3 CH2OCO-tert-butyl G-2-17 103-106 402 CH3 H CH3 H G-2-17 235-238 403 CH3 H CH3 CH2OCO-tert-butyl G-2-16 587 **See Index Table G for 1H NMR data. See List 4, G-2-1 to G-2-12. Index Table D compounds# R1 R2 R3 R4 R13 R14 R15 MS 29 Cl H CH3 H CH3 CH3 H 412 30 CH3 H CH3 SO2CF3 CH3 Et H 538 32 CH3 H CH3 H CH3 Et H 406 37 CH3 H CH3 H Et CH3 H 406 38 Cl H CH3 SO2CF3 CH3 CH3 H 545 42 CH3 H CH3 SO2CF3 CH3 CH3 H 524 43 CH3 H CH3 SO2CF3 Etc. Etc. H 552 44 CH3 H CH3 H Etc. Etc. H 420 49 CH3 H CH3 H CH3 CH3 H 392 Index of E compound# R1 R2 R3 R4 R13 R15 R16 MS MP(℃) 27 CH3 H CH3 H CH3 H CN 220-223 28 CH3 H CH3 SO2CF3 CH3 H Et 522 31 CH3 H CH3 H CH3 H F 188 - 191 34 CH3 H CH3 H CH3 H Et 390 35 CH3 H CH3 SO2CF3 CH3 H OMe 524 36 CH3 H CH3 H CH3 H SMe 212 - 215 39 CH3 H CH3 SO2Me CH3 H Isopropyl 481 41 CH3 H CH3 H CH3 H Isopropyl 404 45 CH3 H CH3 SO2Me Et H Cl 488 46 CH3 H CH3 SO2Me CH3 H Cl 474 47 CH3 H CH3 SO2CF3 CH3 H Isopropyl 536 48 CH3 H CH3 SO2Me Et H H 440 51 CH3 H CH3 H Et H Cl 410 52 CH3 H CH3 SO2CF3 Et H CH3 522 53 CH3 H CH3 COOMe CH3 H H 420 55 CH3 H F H Et H<00​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​ 348 61 CH3 H CH3 SO2CF3 CH3 H CF3 562 62 CH3 H CH3 H CH3 H CH3 376 63 CH3 H F H CH3 H H 366 64 CH3 H CH3 H CH3 OMe Cl 425 65 CH3 H CH3 H CH3 OMe H 391 66 CH3 H H SO2CF3 CH3 H H 480 67 CH3 H CH3 SO2CF3 CH3 H Br 572 68 CH3 H CH3 H Et H CH3 390 69 CH3 H CH3 H CH3 H Br 440 70 CH3 H CH3 H CH3 H OMe 392 71 CH3 H CH3 H CH3 H CF3 430 72 CH3 H CH3 H CH3 H Cl 396 73 CH3 H CH3 SO2Me CH3 H H 439 74 CH3 H CH3 SO2CF3 CH3 H Cl 527 75 CH3 H CH3 SO2CF3 CH3 H<00所8285> CH3 508 76 CH3 H CH3 SO2CF3 CH3 H H 494 77 CH3 H CH3 H Isobutyl H H 404 78 CH3 H CH3 H Isopropyl H H 390 79 CH3 H CH3 H Et H H 376 80 CH3 H CH3 H CH3 H H 172 - 175 81 CH3 H OMe H CH3 H H 378 Index Table F Compound # R1 R2 R3 R4 R16 R17 R18 M.S. 40 CH3 H CH3 S(O)2CF3 H OMe OMe 541 54 CH3 H CH3 H H H OMe 378 60 CH3 H CH3 H H OMe H 378 82 CH3 H CH3 H H Cl H 382 83 CH3 H CH3 H H H H 348 84 CH3 H CH3 H H Me H 362 85 CH3 H CH3 H Me H H 361 281 CH3 H CH3 H H Me H 259-262 282 CH3 H CH3 H H OMe OMe 230-233 Index table G Compound # R1 R2 R3 R4 Rw MS MP (°C) 404 CH3 H CH3 CH2OCO-tert-butyl H 379 405 CH3 H CH3 H H 507 406 CH3 H CH3 H 2-CH3 505 407 CH3 H CH3 CH2OCO-tert-butyl 2-CH3 391 408 CH3 H CH3 H 1-CH3 64-67 409 CH3 H CH3 H 2-Cl 513 410 CH3 H CH3 CH2OCO-tert-butyl 1-CH3 555 411 CH3 H CH3 CH2OCO-tert-butyl 2-Cl 439 412 CH3 H CH3 H 1-OMe 481 413 CH3 H CH3 CH2OCO-tert-butyl 1-OMe 189-192 414 CH3 H CH3 CH2OCO-tert-butyl 1-OEt 287-290 415 CH3 H CH3 H 1-Br 211-214 416 CH3 H CH3 H 1-Cl 513 417 CH3 H CH3 CH2OCO-tert-butyl 1-Cl 91-94 418 CH3 H CH3 CH2OCO-tert-butyl 1-Br 214-218 Index table H Compound numbering 1H NMR data (unless otherwise stated, in CDCl3 solution at 500 MHz) a 157 δ 7.29 (s, 1H), 7.15 (s, 1H), 3.81-3.95 (m, 4H), 3.67 (s, 2H), 2.40 (s, 3H), 2.33 (s, 3H), 2.05-2.09 (m, 2H), 1.89-1.98 (m, 2H). 275 δ 7.29 (s, 1H), 7.17 (s, 1H), 3.83 (s, 2H), 2.40 (s, 3H), 2.34 (s, 3H), 2.23-2.29 (m, 2H), 1.90-1.99 (m, 2H), 1.77-1.84 (m, 4H). α 1H NMR data are expressed in ppm in the low-field region of tetramethylsilane. Coupling is indicated by (s)-single and (m)-multiplexes. Biological Examples of the Invention Test A

[0372] Seeds of plant species selected from Echinochloa crus-galli, Kochia scoparia, Ambrosia artemisiifolia, Lolium multiflorum, Setaria faberi, and Amaranthus retroflexus were planted in a mixture of soil and sand and pre-germination was performed by targeted soil spraying using test chemicals, including surfactants, formulated in a non-phytotoxic solvent mixture.

[0373] Simultaneously, plants selected from these weed species, as well as wheat (Triticum aestivum), corn (Zea mays), black grass (Alopecurus myosuroides), and cleavers (Catchweed bedstraw, Galium aparine), were planted in containers containing the same soil and sand mixture, and post-germination treatment was performed using the test chemical (prepared in the same manner). Post-germination treatment was applied to plants ranging in height from 2 to 10 cm and at the one- to two-leaf stage. The treated plants and the untreated control group were maintained in a greenhouse for approximately 10 days, after which all treated plants were compared to the untreated control group, and damage was visually assessed. The plant response ratings extracted in Table A are based on a scale of 0 to 100, where 0 represents no effect and 100 represents complete control. A response shown as a dash (-) indicates no test results. Table A compound 1000 g ai / ha 4 5 6 7 8 10 11 12 19 50 242 258 259 260 Pre-moe barnyard grass 100 100 100 80 100 40 100 100 100 100 100 80 90 100 Foxtail grass 100 100 100 90 100 80 100 100 100 100 100 90 90 100 Earth Skin 80 90 100 30 100 60 90 90 90 90 90 90 40 40 quinoa 100 100 100 80 100 100 100 100 100 100 100 100 80 100 pig feed - - - 80 90 90 80 - 90 80 90 90 70 90 Italian ryegrass 100 100 100 60 100 90 0 100 90 70 100 70 80 100 Table A compound 1000 g ai / ha 261 262 263 264 Pre-moe barnyard grass 60 20 30 100 Foxtail grass 90 70 70 100 Kochia scoparia 0 0 20 70 quinoa 20 0 60 80 pig feed 0 0 - 90 Italian ryegrass 60 20 50 100 Table A compound 500 g ai / ha 9 13 14 15 16 17 18 20 twenty one twenty two twenty three twenty four 25 26 Pre-moe barnyard grass 100 100 90 0 100 100 100 100 100 100 100 100 100 100 Foxtail grass 100 10 80 70 100 100 100 100 100 80 100 100 100 100 Kochia scoparia 90 50 90 80 90 90 60 90 0 50 80 90 80 50 quinoa 80 60 90 70 100 100 100 80 60 100 100 90 100 90 pig feed 90 - - - 100 80 30 100 - - - - - 50 Italian ryegrass 100 30 100 30 100 100 90 100 100 100 100 100 100 100 Table A compound 500 g ai / ha 28 29 30 32 34 35 37 38 39 40 41 42 43 Pre-moe barnyard grass 100 100 90 100 0 90 90 100 90 90 90 100 100 Foxtail grass 90 100 100 100 30 90 100 100 90 100 80 100 100 Kochia scoparia 90 90 90 90 70 20 90 90 0 80 0 70 90 quinoa - 90 60 60 - 80 90 80 0 100 0 80 60 pig feed 30 90 40 50 20 80 80 90 30 50 80 80 0 Italian ryegrass 90 100 90 100 70 50 100 100 70 80 80 100 100 Table A compound 500 g ai / ha 44 45 46 47 48 51 52 53 54 55 56 57 58 59 Pre-moe barnyard grass 100 100 70 90 100 100 100 0 0 100 100 100 100 90 Foxtail grass 100 100 90 90 100 100 100 0 10 100 20 100 100 70 Kochia scoparia 60 100 0 0 30 90 80 0 90 80 100 60 80 90 quinoa 100 90 50 0 80 90 80 0 90 90 90 80 50 60 pig feed 10 80 0 60 90 90 60 40 90 90 90 70 0 30 Italian ryegrass 100 100 80 100 100 100 90 0 20 90 100 90 100 60 Table A compound 500 g ai / ha 60 61 62 63 64 65 66 67 68 69 70 71 72 73 Pre-moe barnyard grass 90 100 100 90 90 90 90 100 100 90 100 100 100 90 Foxtail grass 90 100 100 100 90 100 60 100 100 100 90 100 100 100 Kochia scoparia 90 90 90 90 90 60 40 70 90 90 0 40 100 90 quinoa 100 80 90 90 50 30 30 80 90 100 80 60 100 100 pig feed 70 0 80 80 40 0 10 60 90 90 70 60 90 80 Italian ryegrass 90 100 100 100 100 60 0 90 100 100 60 100 100 100 Table A compound 500 g ai / ha 74 75 76 77 78 79 80 81 82 83 84 85 99 100 Pre-moe barnyard grass 100 100 90 90 100 100 90 90 80 80 80 70 100 90 Foxtail grass 100 100 100 100 100 100 100 100 60 80 90 90 80 90 Kochia scoparia 100 100 90 0 60 90 80 80 90 70 70 70 100 80 quinoa 100 100 100 30 90 100 90 100 80 90 70 100 100 80 pig feed 90 80 90 20 90 90 90 40 20 20 0 0 90 80 Italian ryegrass 100 100 100 90 100 100 90 50 40 50 90 30 90 70 Table A compound 500 g ai / ha 101 102 103 104 105 107 108 109 110 114 116 119 120 Pre-moe barnyard grass 100 100 90 100 100 100 100 100 90 80 90 100 100 Foxtail grass 100 90 100 100 100 100 100 100 100 100 90 100 100 Kochia scoparia 90 90 90 50 100 50 90 100 100 70 100 100 100 quinoa 90 100 100 90 100 90 - 100 100 - - 100 - pig feed 80 70 90 60 80 80 60 90 90 10 100 100 100 Italian ryegrass 100 90 90 100 100 90 100 80 90 90 90 100 100 Table A compound 500 g ai / ha 121 122 123 124 125 126 127 128 129 130 132 133 134 135 Pre-moe barnyard grass 90 70 100 0 100 40 90 100 90 100 100 90 40 100 Foxtail grass 100 100 100 20 100 90 90 100 100 100 90 90 100 100 Kochia scoparia 90 30 80 0 100 30 80 80 90 100 70 0 0 100 quinoa - 30 100 80 100 100 40 100 100 100 100 90 90 100 pig feed 100 0 80 30 80 30 60 90 90 90 90 90 30 80 Italian ryegrass 100 80 100 0 100 40 80 100 100 100 100 90 90 100 Table A compound 500 g ai / ha 136 139 140 141 142 146 147 158 159 160 163 164 165 166 Pre-moe barnyard grass 100 30 100 100 100 100 100 100 60 100 100 100 30 100 Foxtail grass 100 20 90 100 100 100 100 100 70 100 90 100 90 100 Kochia scoparia 90 60 70 50 0 80 90 80 70 90 80 100 100 100 quinoa 70 70 50 90 100 - - 100 - 100 100 - - - pig feed 80 30 60 90 70 70 90 40 80 90 60 100 100 80 Italian ryegrass 100 70 100 100 100 100 100 100 30 60 100 100 70 100 Table A compound 500 g ai / ha 169 170 171 172 173 175 176 177 178 179 180 181 182 183 Pre-moe barnyard grass 100 0 100 90 90 100 90 100 100 90 80 100 50 100 Foxtail grass 90 20 100 100 100 100 100 100 100 100 90 100 10 70 Kochia scoparia 30 0 90 90 90 100 90 100 100 90 0 100 70 60 quinoa 80 90 - - - 100 - 100 100 - 70 80 70 80 pig feed 80 0 90 90 90 100 90 90 90 90 70 90 60 90 Italian ryegrass 100 40 100 100 100 100 100 100 100 100 50 90 80 100 Table A compound 500 g ai / ha 184 185 186 187 188 189 190 191 192 193 194 195 196 197 Pre-moe barnyard grass 100 100 100 100 90 100 100 100 70 90 90 90 90 100 Foxtail grass 90 100 100 100 100 100 100 100 90 100 100 90 100 100 Kochia scoparia 0 0 70 80 60 100 100 90 80 40 90 0 80 90 quinoa 100 80 80 80 90 100 100 100 100 90 100 80 100 100 pig feed 90 70 50 90 50 90 90 100 90 90 90 0 0 90 Italian ryegrass 50 100 100 100 100 100 100 100 100 100 100 90 70 100 Table A compound 500 g ai / ha 198 199 200 201 202 203 204 205 206 207 208 209 210 211 Pre-moe barnyard grass 100 100 100 100 90 90 90 90 90 90 90 90 100 90 Foxtail grass 100 100 100 100 70 100 100 100 90 100 100 70 100 90 Kochia scoparia 80 90 90 100 80 90 90 80 90 90 90 80 90 90 quinoa 100 100 100 100 100 100 100 90 100 100 70 50 100 90 pig feed 80 90 90 100 90 90 90 80 80 70 0 60 90 80 Italian ryegrass 90 80 90 90 70 100 100 100 90 100 80 90 100 70 Table A compound 500 g ai / ha 212 213 214 215 216 217 218 219 220 221 222 223 224 225 Pre-moe barnyard grass 90 50 0 90 80 100 100 100 100 100 90 50 100 90 Foxtail grass 90 80 60 70 90 100 100 90 100 100 50 100 100 100 Kochia scoparia 90 90 90 90 90 90 60 40 70 90 40 20 90 40 quinoa 90 100 60 90 100 100 90 60 100 100 100 90 100 100 pig feed 30 20 60 20 30 90 90 0 60 90 90 50 80 90 Italian ryegrass 70 90 90 70 90 100 100 60 100 100 80 80 100 100 Table A compound 500 g ai / ha 226 227 228 229 230 231 232 233 234 235 236 237 238 239 Pre-moe barnyard grass 100 90 100 90 100 100 100 30 80 0 0 30 0 20 Foxtail grass 100 100 100 100 100 100 100 100 50 10 60 40 60 60 Kochia scoparia 90 90 90 100 80 90 80 80 30 50 70 90 60 80 quinoa 100 80 100 100 100 100 100 90 100 80 90 100 80 90 pig feed 90 80 70 100 70 100 90 30 90 80 80 80 90 70 Italian ryegrass 100 100 100 90 100 100 100 70 50 90 60 50 90 30 Table A compound 500 g ai / ha 240 241 243 244 245 246 247 248 249 250 251 252 253 254 Pre-moe barnyard grass 50 100 90 90 100 100 50 90 60 90 90 100 70 100 Foxtail grass 80 100 100 100 100 100 90 80 100 100 90 100 100 100 Kochia scoparia 90 100 80 90 80 90 80 90 70 100 90 80 80 80 quinoa 80 100 100 - - 100 90 90 80 100 100 100 100 90 pig feed 50 90 80 90 90 90 30 90 0 90 80 90 40 60 Italian ryegrass 70 100 100 80 100 100 90 90 80 90 100 100 100 90 Table A compound 500 g ai / ha 255 256 257 265 266 267 268 269 270 276 277 278 279 280 Pre-moe barnyard grass 90 100 70 100 40 100 50 100 90 100 100 100 100 90 Foxtail grass 100 90 90 100 20 100 70 100 100 100 100 100 100 100 Kochia scoparia 90 90 80 90 0 100 70 100 0 0 100 100 90 70 quinoa 100 100 90 - - - - - 100 100 100 - 100 100 pig feed 90 80 80 90 0 100 90 90 80 70 80 100 100 70 Italian ryegrass 90 100 90 100 0 100 60 100 100 80 100 100 100 100 Table A compound 125 g ai / ha 1 2 3 9 13 14 15 16 17 18 20 twenty one twenty two twenty three Pre-moe barnyard grass 80 60 50 100 60 - 0 90 100 100 100 80 90 90 Foxtail grass 90 80 50 80 0 70 10 30 100 100 80 20 50 70 Kochia scoparia 70 50 80 70 20 70 0 90 70 10 40 0 20 80 quinoa 100 100 100 30 20 80 60 100 90 100 20 40 30 80 pig feed 50 90 70 90 - - - 80 80 0 90 - - - Italian ryegrass 90 50 70 90 20 60 30 90 80 90 50 30 60 40 Table A compound 125 g ai / ha twenty four 25 26 27 28 29 30 32 34 35 36 37 38 Pre-moe barnyard grass 100 100 70 0 60 40 90 100 0 70 50 90 90 Foxtail grass 30 100 100 60 30 100 80 100 0 60 80 100 100 Kochia scoparia 90 70 0 0 70 40 70 60 30 0 0 80 80 quinoa 60 80 80 20 - 70 20 20 - 50 10 50 40 pig feed - - 20 0 0 60 20 0 0 20 0 40 70 Italian ryegrass 70 70 80 0 50 90 90 100 30 40 60 100 100 Table A compound 125 g ai / ha 39 40 41 42 43 44 45 46 47 48 51 52 53 54 Pre-moe barnyard grass 40 90 50 90 90 100 90 0 50 90 100 100 0 0 Foxtail grass 10 90 10 100 100 100 100 90 10 100 100 100 0 0 Kochia scoparia 0 80 0 40 0 0 70 0 0 30 80 70 0 60 quinoa 0 100 0 40 20 40 60 0 0 70 80 50 0 40 pig feed 0 50 30 30 0 0 60 0 20 80 60 10 0 50 Italian ryegrass 30 30 60 100 100 100 80 50 50 60 90 90 0 0 Table A compound 125 g ai / ha 55 56 57 58 59 60 61 62 63 64 65 66 67 68 Pre-moe barnyard grass 0 100 100 100 0 90 100 100 70 50 0 0 70 100 Foxtail grass 60 0 100 100 20 80 100 100 90 90 80 0 90 100 Earth Skin 80 40 60 0 40 90 50 70 40 40 0 0 0 70 quinoa 70 40 50 0 30 100 50 50 70 40 0 0 50 70 pig feed 20 70 40 0 0 30 0 20 30 0 0 0 0 30 Italian ryegrass 70 100 90 70 0 80 70 40 90 70 30 0 80 90 Table A compound 125 g ai / ha 69 70 71 72 73 74 75 76 77 78 79 80 81 82 Pre-moe barnyard grass 40 90 0 90 90 90 90 90 90 90 100 90 90 40 Foxtail grass 100 10 80 100 100 100 100 100 90 100 100 90 100 0 Earth Skin 70 0 80 100 80 70 80 60 0 0 70 80 0 70 quinoa 80 80 40 80 90 60 80 50 20 30 90 60 30 90 pig feed 50 10 10 80 80 70 20 70 0 80 80 70 30 0 Italian ryegrass 100 50 70 90 90 80 80 60 0 100 90 90 30 20 Table A compound 125 g ai / ha 83 85 88 91 92 93 94 95 96 97 98 99 100 101 Pre-moe barnyard grass 70 70 30 90 60 80 90 80 70 90 90 90 70 100 Foxtail grass 10 10 90 100 70 80 100 100 80 50 100 70 40 90 Earth Skin 60 60 40 60 0 50 60 10 0 0 40 70 60 60 quinoa 50 100 90 10 20 100 100 90 90 100 100 100 70 90 pig feed 0 0 20 20 20 70 30 60 30 0 80 60 20 60 Italian ryegrass 30 0 - 50 30 80 90 90 80 0 50 50 40 80 Table A compound 125 g ai / ha 102 103 104 105 107 108 109 110 111 112 113 114 115 Pre-moe barnyard grass 80 90 90 90 90 70 90 40 30 30 20 50 100 Foxtail grass 80 90 90 90 60 80 100 90 60 50 60 90 100 Earth Skin 70 80 0 20 0 80 90 80 50 60 50 30 40 quinoa 100 100 70 100 80 - 100 80 90 100 90 - 90 pig feed 20 70 30 70 50 20 90 80 70 90 60 0 20 Italian ryegrass 90 90 50 100 60 90 70 20 70 30 80 70 90 Table A compound 125 g ai / ha 116 118 119 120 121 122 123 124 125 126 127 128 129 130 Pre-moe barnyard grass 30 90 100 90 90 0 100 0 100 0 50 100 100 100 Foxtail grass 60 100 100 100 100 50 100 0 100 20 20 50 100 100 Earth Skin 90 0 50 90 90 70 40 0 90 0 80 80 80 60 quinoa - 100 100 - - 0 90 20 100 70 20 100 100 100 pig feed 10 100 80 90 80 0 50 0 60 0 0 90 70 80 Italian ryegrass 40 80 80 100 100 30 90 0 100 0 60 100 80 90 Table A compound 125 g ai / ha 131 132 133 134 135 136 137 139 140 141 142 143 144 145 Pre-moe barnyard grass 90 60 30 0 100 90 100 0 40 100 90 90 100 50 Foxtail grass 100 30 10 40 100 100 100 0 20 100 100 100 100 10 Earth Skin 40 0 0 0 80 80 30 0 0 0 0 20 30 0 quinoa 90 100 30 80 60 20 100 20 0 90 90 100 50 70 pig feed 40 80 20 10 10 50 60 0 30 50 30 0 30 40 Italian ryegrass 80 80 20 20 100 90 100 50 0 90 90 90 90 40 Table A compound 125 g ai / ha 146 147 148 149 150 151 152 153 154 155 156 157 158 159 Pre-moe barnyard grass 90 90 80 0 90 90 70 70 50 90 100 100 30 40 Foxtail grass 100 90 100 80 100 100 80 90 90 80 100 100 90 30 Earth Skin 80 70 30 0 0 0 0 80 40 40 50 90 70 40 quinoa - - 100 70 100 90 100 90 100 100 100 100 50 - pig feed 60 90 20 0 0 30 30 60 80 80 90 90 30 80 Italian ryegrass 90 90 100 50 90 90 40 70 70 80 70 60 30 0 Table A compound 125 g ai / ha 160 161 162 153 164 165 166 167 168 169 170 171 172 173 Pre-moe barnyard grass 80 100 60 90 90 20 100 20 60 30 0 90 90 90 Foxtail grass 90 80 90 50 90 80 80 10 0 20 0 100 90 100 Earth Skin 20 90 40 0 100 90 90 40 20 0 0 70 60 60 quinoa 90 100 100 50 - - - 20 10 60 20 - - - pig feed 10 90 30 20 90 50 20 0 0 40 0 80 40 90 Italian ryegrass 50 100 70 80 80 50 70 60 40 50 20 100 100 90 Table A compound 125 g ai / ha 174 175 176 177 178 179 180 181 182 183 184 185 186 187 Pre-moe barnyard grass 80 90 70 80 90 90 0 90 0 90 70 70 60 100 Foxtail grass 90 100 100 70 90 80 0 100 10 50 30 50 60 100 Earth Skin 80 90 70 100 90 90 0 60 30 20 0 0 20 80 quinoa 100 90 - 80 100 - 20 40 50 70 70 50 20 70 pig feed 90 80 40 70 80 90 20 50 30 20 80 20 20 70 Italian ryegrass 60 90 90 100 90 100 0 80 30 70 30 50 60 100 Table A compound 125 g ai / ha 188 189 190 191 192 193 194 195 196 197 198 199 200 201 Pre-moe barnyard grass 60 80 90 100 30 - 90 60 0 90 80 30 30 50 Foxtail grass 0 100 90 100 10 70 80 70 30 100 100 90 90 50 Earth Skin 20 80 90 90 20 0 40 0 70 90 60 0 60 90 quinoa 50 90 100 100 70 60 90 60 50 80 70 80 100 100 pig feed 40 80 70 60 30 70 80 0 0 80 70 50 40 70 Italian ryegrass 50 90 70 70 50 60 30 20 20 100 60 50 30 60 Table A compound 125 g ai / ha 202 203 204 205 206 207 208 209 210 211 212 213 214 215 Pre-moe barnyard grass 30 90 90 50 90 90 90 40 90 60 0 20 0 60 Foxtail grass 60 30 80 50 80 90 90 20 90 60 20 30 40 40 Earth Skin 40 60 40 0 80 90 90 0 30 80 30 80 70 80 quinoa 100 60 90 70 90 100 60 0 100 20 90 50 30 100 pig feed 70 80 10 40 40 20 0 0 80 30 0 0 0 0 Italian ryegrass 40 50 90 60 80 90 70 50 50 50 30 60 60 20 Table A compound 125 g ai / ha 216 217 218 219 220 221 222 223 224 225 226 227 228 229 Pre-moe barnyard grass 40 90 100 0 100 100 - 30 70 70 90 60 100 70 Foxtail grass 20 90 100 50 100 100 40 60 90 90 90 90 90 60 Earth Skin 100 70 30 20 20 70 0 0 0 0 40 60 60 80 quinoa 80 70 80 40 70 60 50 10 100 70 80 50 100 100 pig feed 0 60 20 0 30 90 60 0 50 30 30 30 10 90 Italian ryegrass 30 80 100 50 100 100 30 30 50 70 90 40 100 60 Table A compound 125 g ai / ha 230 231 232 233 234 235 236 237 238 239 240 241 243 244 Pre-moe barnyard grass 70 90 100 0 80 0 0 40 0 0 0 100 80 70 Foxtail grass 100 100 100 40 50 10 30 20 30 20 30 80 100 50 Kochia scoparia 60 0 0 0 0 30 20 90 80 30 70 70 20 80 quinoa 100 100 100 60 50 30 60 80 20 60 0 100 100 - pig feed 0 80 70 0 80 40 50 30 20 20 30 70 70 90 Italian ryegrass 20 80 100 20 20 50 20 20 60 0 40 70 90 50 Table A compound 125 g ai / ha 245 246 247 248 249 250 251 252 253 254 255 256 257 265 Pre-moe barnyard grass 90 40 0 80 60 40 20 40 60 30 40 90 40 90 Foxtail grass 100 90 50 40 50 90 50 100 100 20 90 30 70 100 Kochia scoparia 80 40 0 90 0 80 90 60 70 70 70 60 60 90 quinoa - 90 90 90 80 100 100 100 100 70 100 100 100 - pig feed 90 80 0 80 0 80 80 80 40 10 20 60 30 90 Italian ryegrass 80 70 20 70 40 60 90 60 60 80 80 80 60 90 Table A compound 125 g ai / ha 266 267 268 269 270 276 277 278 279 280 Pre-moe barnyard grass 0 100 40 100 90 70 100 60 100 90 Foxtail grass 0 100 50 100 100 100 100 60 100 100 Kochia scoparia 0 80 70 70 0 0 90 90 80 40 quinoa - - - - 70 80 60 - 90 70 pig feed 0 100 40 80 0 40 10 90 100 30 Italian ryegrass 0 90 0 80 100 30 100 100 90 100 Table A compound 31 g ai / ha 1 2 3 27 36 88 91 92 93 94 95 96 97 98 Pre-moe barnyard grass 0 0 0 0 0 20 0 0 0 10 10 10 0 0 Foxtail grass 20 80 20 10 20 60 20 0 60 50 90 40 0 80 Kochia scoparia 40 20 30 0 0 30 0 0 0 0 0 0 0 40 quinoa 70 100 90 0 0 0 60 0 50 100 70 20 10 70 pig feed 30 30 0 0 0 0 0 0 0 0 0 0 0 30 Italian ryegrass 40 30 20 0 0 0 30 0 0 30 20 0 0 30 Table A compound 31 g ai / ha 111 112 113 115 118 131 137 143 144 145 148 149 150 151 Pre-moe barnyard grass 10 20 0 50 0 70 20 80 20 0 20 0 0 0 Foxtail grass 0 - 10 100 80 90 50 50 90 0 40 30 20 60 Kochia scoparia 0 10 10 0 0 30 30 0 0 0 20 0 0 0 quinoa 10 50 30 100 100 30 80 60 70 20 30 30 40 50 pig feed 10 30 0 0 50 0 20 0 0 0 0 0 0 0 Italian ryegrass 0 0 0 70 40 30 60 90 70 0 60 50 40 30 Table A compound 31 g ai / ha 152 153 154 155 156 157 161 162 167 168 174 Pre-moe barnyard grass 0 0 0 50 70 30 20 0 0 0 10 Foxtail grass 40 40 60 50 50 80 40 100 0 0 30 Kochia scoparia 0 60 0 30 30 50 30 30 30 0 40 quinoa 30 80 20 90 80 100 70 100 0 0 90 pig feed 0 40 50 90 60 40 90 0 0 0 30 Italian ryegrass 0 30 20 80 50 40 70 40 30 0 40 Table A compound 1000 g ai / ha 4 5 6 7 8 10 11 12 19 50 242 258 259 260 Cute Queen barnyard grass 90 80 90 20 80 10 90 80 80 60 90 70 0 90 Black Grass 40 0 60 20 70 0 50 30 60 20 40 50 50 50 corn 40 10 60 0 30 10 60 20 50 10 70 10 10 10 Foxtail grass 90 90 90 0 90 20 90 90 90 90 90 50 0 50 Pig calamity 90 90 90 40 20 80 90 90 40 90 90 80 60 70 Earth Skin 80 80 80 40 80 40 60 70 70 60 80 90 40 0 quinoa 80 80 100 20 80 80 100 80 80 90 90 80 40 80 pig feed 80 80 50 20 90 80 80 60 80 50 90 80 10 50 Italian ryegrass 80 30 80 90 80 60 70 90 50 90 0 70 10 60 wheat 70 60 60 0 40 0 80 60 50 50 60 30 0 60 Table A compound 1000 g ai / ha 261 262 263 264 Cute Queen barnyard grass 0 0 30 50 Black Grass 0 20 20 60 corn 10 0 20 20 Foxtail grass 0 0 0 40 Pig calamus 50 40 60 70 Kochia scoparia 0 0 10 20 quinoa 30 20 0 60 pig feed 0 0 0 60 Italian ryegrass 20 20 80 50 wheat 0 0 0 70 Table A compound 500 g ai / ha 9 13 14 15 16 17 18 20 twenty one twenty two twenty three twenty four 25 26 Cute Queen barnyard grass 90 40 80 50 90 90 70 80 40 50 70 90 80 70 Black Grass 30 0 40 30 40 30 0 30 10 0 30 30 20 30 corn 70 0 20 0 50 20 0 70 30 30 70 40 0 20 Foxtail grass 90 10 70 50 90 90 70 90 20 60 90 60 80 40 Pig calamus 90 30 80 60 90 90 80 90 60 90 90 90 80 90 Kochia scoparia 30 10 70 70 80 70 40 30 30 40 70 80 60 10 quinoa 80 20 90 30 90 70 90 80 40 - 80 100 70 90 pig feed 80 30 70 80 90 90 80 80 90 50 80 80 90 100 Italian ryegrass 80 0 30 0 70 70 40 70 50 60 80 40 60 0 wheat 70 0 70 0 70 60 70 70 30 60 70 80 70 60 Table A compound 500 g ai / ha 28 29 30 32 34 35 37 38 39 40 41 42 43 Cute Queen barnyard grass 80 90 90 90 0 80 90 80 30 40 80 80 90 Black Grass 30 90 80 90 0 30 90 90 0 10 40 90 90 corn 0 10 40 80 0 0 80 70 0 0 0 60 80 Foxtail grass 10 90 90 90 0 10 90 90 0 10 30 90 90 Pig calamus 70 90 90 90 0 70 100 90 0 70 30 60 90 Kochia scoparia 30 80 50 40 50 10 70 70 0 20 0 30 40 quinoa 40 50 60 20 0 60 50 90 0 30 0 100 80 pig feed 80 90 40 60 0 40 70 90 70 40 70 80 60 Italian ryegrass 0 90 70 90 0 40 90 80 40 60 60 80 50 wheat 50 70 70 70 0 40 80 70 60 40 60 70 70 Table A compound 500 g ai / ha 44 45 46 47 48 51 52 53 54 55 56 57 58 59 Cute Queen barnyard grass 90 70 0 80 80 80 80 0 10 40 90 90 90 80 Black Grass 90 60 0 50 40 70 80 0 0 20 50 70 30 70 corn 70 30 0 0 80 20 0 0 10 50 80 80 50 40 Foxtail grass 90 60 0 80 90 80 80 0 0 90 90 90 90 70 Pig calamus 90 40 0 40 90 60 80 80 90 90 90 90 90 90 Kochia scoparia 30 50 0 0 10 60 80 0 80 80 60 20 20 70 quinoa 90 70 0 0 60 80 50 0 70 70 40 50 0 60 pig feed 50 70 0 80 90 80 60 20 90 40 90 30 20 60 Italian ryegrass 30 90 0 80 90 80 40 0 40 60 80 90 60 60 wheat 70 70 50 60 70 60 70 0 0 70 70 70 70 40 Table A compound 500 g ai / ha 60 61 62 63 64 65 66 67 68 69 70 71 72 73 Cute Queen barnyard grass 70 80 70 90 20 70 30 40 80 80 50 80 - - Black Grass 70 30 50 40 30 0 0 60 70 50 30 70 80 80 corn 60 10 0 50 0 0 10 0 20 20 0 30 50 70 Foxtail grass 90 70 80 90 60 40 30 70 90 90 20 90 90 90 Pig calamus 90 60 80 90 30 30 70 60 80 70 80 80 90 90 Kochia scoparia 80 60 40 90 60 0 10 40 50 60 0 40 90 70 quinoa 90 80 40 80 30 0 50 80 50 90 20 90 80 80 pig feed 70 30 20 60 0 0 0 10 80 80 0 0 70 80 Italian ryegrass 80 80 20 70 80 0 0 60 80 70 0 80 80 90 wheat 70 70 60 80 60 50 40 60 80 70 30 70 70 70 Table A compound 500 g ai / ha 74 75 76 77 78 79 80 81 82 83 84 85 99 100 Cute Queen barnyard grass - - - 20 70 90 90 80 20 70 80 20 90 90 Black Grass 50 70 50 0 30 30 100 70 0 0 20 0 20 0 corn 10 0 70 60 50 70 80 20 40 30 60 0 0 30 Foxtail grass 80 90 90 40 90 90 90 90 50 40 50 0 10 40 Pig calamus 90 90 100 40 90 90 90 90 10 80 50 0 90 90 Kochia scoparia 90 80 90 10 20 70 70 50 0 20 0 0 90 90 quinoa 90 80 90 0 50 80 70 60 40 50 30 40 100 90 pig feed 30 50 90 10 40 80 90 60 30 60 40 30 80 80 Italian ryegrass 70 60 80 0 60 80 80 60 0 0 50 30 60 40 wheat 70 70 80 70 70 80 80 60 0 0 70 0 50 50 Table A compound 500 g ai / ha 101 102 103 104 105 107 108 109 110 114 116 119 120 Cute Queen barnyard grass 90 90 90 90 90 90 90 70 80 70 90 90 90 Black Grass 20 0 30 20 50 30 50 10 0 50 40 40 70 corn 30 30 70 80 90 80 50 40 10 50 80 30 70 Foxtail grass 80 70 70 70 90 50 30 40 90 80 80 80 90 Pig calamus 90 100 100 90 90 90 90 90 80 90 90 90 90 Kochia scoparia 30 90 80 40 80 40 80 40 50 40 70 60 90 quinoa 90 80 80 80 80 60 60 80 100 80 80 70 90 pig feed 70 90 70 90 90 90 80 80 90 30 90 90 90 Italian ryegrass 70 90 90 40 90 30 70 60 50 40 80 90 80 wheat 60 80 80 60 70 40 70 70 60 60 80 70 70 Table A compound 500 g ai / ha 121 122 123 124 125 126 127 128 129 130 132 133 134 135 Cute Queen barnyard grass 90 70 90 0 90 0 70 90 80 90 40 10 10 90 Black Grass 80 10 50 20 60 30 20 30 30 10 0 0 0 60 corn 80 0 70 10 60 20 20 60 20 90 20 10 0 80 Foxtail grass 90 20 80 0 50 0 0 50 30 90 40 10 10 90 Pig calamity 90 90 90 80 90 90 90 90 80 90 90 90 80 90 Kochia scoparia 80 10 70 20 80 30 40 70 50 70 20 20 70 70 quinoa 90 50 80 50 90 90 40 90 90 90 90 90 90 70 pig feed 90 0 70 0 80 30 50 90 90 90 90 80 40 80 Italian ryegrass 80 0 50 0 70 0 50 100 70 90 40 40 0 80 wheat 70 0 60 0 70 0 0 60 60 70 0 50 0 70 Table A compound 500 g ai / ha 136 139 140 141 142 146 147 158 159 160 163 164 165 166 Cute Queen barnyard grass 80 0 90 90 90 80 90 20 80 80 80 90 30 90 Black Grass 20 0 30 20 20 20 30 0 20 10 30 40 10 20 corn 30 0 30 90 90 20 80 20 30 10 60 80 0 50 Foxtail grass 50 0 90 50 90 90 90 20 30 60 10 40 0 60 Pig calamity 90 80 70 90 90 90 90 90 90 90 90 90 90 90 Kochia scoparia 40 50 60 50 40 50 70 30 40 30 60 90 60 80 quinoa 90 80 80 90 80 80 90 80 70 90 80 90 90 90 pig feed 50 0 50 90 90 90 90 20 90 80 30 90 60 80 Italian ryegrass 0 0 20 90 80 70 70 0 0 0 30 90 30 90 wheat 60 0 60 70 70 60 60 0 50 20 0 70 0 70 Table A compound 500 g ai / ha 169 170 171 172 173 175 176 177 178 179 180 181 182 183 Cute Queen barnyard grass 90 20 90 80 90 90 90 90 90 90 10 90 30 70 Black Grass 20 0 80 40 60 20 70 30 0 40 20 30 0 10 corn 90 30 80 70 80 10 80 50 10 80 0 80 60 30 Foxtail grass 40 80 90 80 90 30 90 60 20 90 10 90 60 10 Pig calamity 90 90 90 90 90 90 90 90 90 90 90 70 40 90 Kochia scoparia 50 40 70 80 80 50 50 70 70 70 40 80 20 50 quinoa 50 80 80 90 90 90 90 90 90 90 70 80 70 30 pig feed 90 30 90 80 90 90 90 90 80 90 70 90 90 80 Italian ryegrass 30 0 80 80 80 80 80 90 30 80 0 90 80 0 wheat 0 30 60 70 70 80 60 80 30 60 0 80 70 0 Table A compound 500 g ai / ha 184 185 186 187 188 189 190 191 192 193 194 195 196 197 Cute Queen barnyard grass 50 20 20 90 70 90 90 30 60 80 80 0 - - Black Grass 20 10 20 20 0 20 40 0 0 60 0 0 0 60 corn 0 0 30 90 30 80 30 10 70 10 0 0 0 80 Foxtail grass 0 0 20 90 20 90 80 20 70 90 80 0 0 90 Pig calamity 90 70 80 80 50 90 90 90 50 90 90 20 80 90 Earth Skin 30 10 40 70 0 80 70 20 20 60 40 0 20 80 quinoa 40 40 50 60 80 90 100 70 80 90 50 0 50 90 pig feed 70 40 60 90 70 90 90 60 80 90 90 50 30 80 Italian ryegrass 0 0 20 80 40 80 90 60 90 80 50 0 30 60 wheat 0 0 30 70 70 70 70 60 80 70 60 0 0 70 Table A compound 500 g ai / ha 198 199 200 201 202 203 204 205 206 207 208 209 210 211 Cute Queen barnyard grass - - - - - 80 80 20 80 80 30 70 90 30 Black Grass 0 50 0 30 0 30 40 0 50 60 20 30 0 0 corn 20 30 20 50 20 60 50 0 70 70 20 30 40 0 Foxtail grass 30 90 20 90 70 50 60 20 60 90 40 10 30 50 Pig calamity 90 90 90 90 80 90 80 70 80 70 70 80 90 70 Earth Skin 60 80 40 90 50 80 70 10 70 60 30 40 90 50 quinoa 70 90 90 100 100 60 70 30 70 70 50 50 100 60 pig feed 80 90 30 90 90 90 80 20 90 70 20 60 90 60 Italian ryegrass 40 70 20 70 70 60 50 0 90 90 40 90 40 30 wheat 40 70 70 70 60 70 70 30 80 70 50 0 60 0 Table A compound 500 g ai / ha 212 213 214 215 216 217 218 219 220 221 222 223 224 225 Cute Queen barnyard grass 0 70 0 40 50 30 90 70 70 80 70 20 - 10 Black Grass 0 20 0 0 30 20 ...

Claims

1. A compound selected from Formula 1, all its stereoisomers, N-oxides and salts, wherein G is selected from R1 being C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl or C1-C7 haloalkyl; and R2 being H, C1-C7 alkyl, halogen, CN, C1-C7 haloalkyl, C1-C7 alkoxy, C3-C7 cycloalkyl or C1-C5 alkylthio; R3 is H, C1-C7 alkyl, halogen, CN, C2-C6 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, or C2-C7 haloalkoxyalkyl; R4 is H, C(=O)R19, -C(=S)R19, -CO2R19, -C(=O)SR19, -S(O)2R19, C(=O)NR19R20, -S(O)2NR19R20, S(OH)2NR19R20, or CH2OC(=O)R19; R7 is H, C1-C7 alkyl, halogen, CN, C1-C7 haloalkyl, or C1-C7 alkoxy; R8 is H, C1-C7 alkyl; or R7 and R8 together form a 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur, or nitrogen atoms as ring members, the ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R9 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl; R7 and R9 may together form a fused 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, the ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy; R10 is H or C1-C7 alkyl;Alternatively, R9 and R10 may form a 3- to 7-membered ring with the attached carbon atom, containing a carbon atom and any 1 to 2 oxygen, sulfur, or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O), or S(O)2, and the ring may be substituted with at most 5 substituents independently selected from (Rv)r, where r is the number of substituents; or Rv is independently selected from the group consisting of: H, halogen, cyano, nitro, C1-C4 alkyl, C3-C 6-cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyclopropylmethyl, propynyl and cyanomethyl; or when two Rv are attached to the same carbon atom or to two adjacent carbon atoms, the two Rv may together with the attached carbon atoms or carbon atoms form a 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2; Q is O, S, CR11R12, or NR13; R11 and R12 together with their attached carbon atoms form a fused 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur, or nitrogen atoms as ring members, the ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; or R9 and R11 together with their attached carbon atoms form a 6-membered aromatic ring, the ring being substituted with any up to 4 substituents independently selected from Rw; Rw is C1-C7 alkyl, halogen, C1-C7 haloalkyl, or C1-C7 alkoxy; r is 0, 1, 2, 3, 4, or 5; R13 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl; R14 is H, C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C1-C7 thioalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl or C4-C7 alkylcycloalkyl; R15 is H, C1-C7 alkyl, halogen, C1-C7 haloalkyl or C1-C7 alkoxy;R16 is H, cyano, C1-C7 alkyl, halogen, C1-C4 alkylthio, C1-C7 haloalkyl, or C1-C7 alkoxy; R17 is H, C1-C7 alkyl, halogen, CN, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl, or C2-C7 haloalkoxyalkyl; R18 is H, C1-C7 alkyl, halogen, C1-C7 haloalkyl, or C1-C7 alkoxy. R19 is a C1-C7 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; C2-C7 alkoxyalkyl, C4-C7 alkylcycloalkyl; R20 is H or a C1-C7 haloalkyl; and Rf is a C1-C7 haloalkyl.

2. The compound of claim 1, all its stereoisomers, N-oxides or salts thereof, wherein Q is O, S or CR11R12.

3. The compound of claim 1, all its stereoisomers, N-oxides or salts thereof, wherein G is G-1; R1 is C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl or C1-C7 haloalkyl; R2 is H, C1-C7 alkyl, C3-C6 cycloalkyl, halogen or CN; R3 is H, C1-C7 alkyl, halogen, CN, C1-C7 alkoxy or C1-C7 haloalkyl; R4 is H, C(=O)R19, CO2R19, C(=O)SR19, S(O)2R19 or CH2OCOR19; and Rf is C1-C3 haloalkyl.

4. The compound of claim 3, all its stereoisomers, N-oxides or salts thereof, wherein R1 is a C1-C7 alkyl, halogen or C3-C7 cycloalkyl; R2 is H, Me or F; R3 is H, Me, F, Cl, CN, OMe or CF3; R4 is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-tertiary butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary butyl or COSMe; R7 is H, C1–C7 alkyl, halogen, CN, C1–C7 haloalkyl or C1–C7 alkoxy; R8 is H or C1–C7 alkyl; R9 R10 is H, C1–C7 alkyl, C1–C7 haloalkyl, or C2–C7 alkoxyalkyl; R10 is H or C1–C7 alkyl; and Rf is CF3.

5. The compound of claim 4, all its stereoisomers, N-oxides or their salts, wherein R1 is Me or Cl; R3 is Me; R4 is H, CH2OCO-tert-butyl or SO2CF3; R7 is H; R8 is H; R9 is methyl, ethyl, tert-butyl, chloromethyl or methoxymethyl; and R10 is methyl or ethyl.

6. The compound of claim 3, all its stereoisomers, N-oxides or salts thereof, wherein R7 and R9 together form a fused 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atom members, the ring being unsubstituted or substituted with at least one independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy; R8 being H; and R10 being H.

7. The compound of claim 6, all its stereoisomers, N-oxides or salts thereof, wherein R1 is a C1-C7 alkyl, halogen or C3-C7 cycloalkyl; R2 is H, Me or F; R3 is H, Me, F, Cl, CN, OMe or CF3; R4 is H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl or COSMe; R7 and R9 together form a fused 3 to 7-membered ring, wherein the 3 to 7-membered ring is a 5 or 6-membered ring.

8. The compound of claim 7, all its stereoisomers, N-oxides or salts thereof, wherein R7 and R9 together form a 5- or 6-membered ring of cyclopentyl, cyclohexyl or tetrahydropiperan, the ring being unsubstituted or substituted with at least one substituent independently selected from the following: H, halogen or C1-C4 alkyl.

9. The compound of claim 3, all its stereoisomers, N-oxides or salts thereof, wherein R9 and R10 together with the attached carbon atom form a 3 to 7-membered ring, containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2, wherein the ring may have at most 5 independently selected from (R The substituents of Rv are substituted and r is the number of substituents; or when two Rv are attached to the same carbon atom or to two adjacent carbon atoms, the two Rv and the attached carbon atoms or groups of carbon atoms may form a 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein at most 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring members are selected from S, S(O) or S(O)2; R7 is H; and R8 is H.

10. The compound of claim 9, all its stereoisomers, N-oxides or salts thereof, wherein R1 is a C1-C3 alkyl, halogen or C3-C4 cycloalkyl; R2 is H, Me or F; R3 is H, Me, F, Cl, CN, OMe or CF3; R4 is H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl or COSMe; R9 and R10 together with the carbon atom to which they are attached form a 3 to 7-membered ring, which is a 5 or 6-membered ring; Rv is independently selected from the group consisting of: H, methyl, ethyl, propyl, cyclopropylmethyl, propyne, or cyanomethyl; and r is 1 or 2.

11. The compound of claim 10, all its stereoisomers, N-oxides or salts thereof, wherein R9 and R10 together with the carbon atom to which they are attached form a 3 to 7-membered ring, the ring being a 5 or 6-membered ring of cyclopentane, cyclohexane, tetrahydro-2H-piperanone or tetrahydro-2H-thiopiperanone.

12. The compound of claim 1, all its stereoisomers, N-oxides or salts thereof, wherein G is G-2; R1 is C1-C7 alkyl, halogen, C2-C6 alkenyl, C2-C6 ynyl, C3-C7 cycloalkyl or C1-C7 haloalkyl; R2 is H, Me or F; R3 is H, Me, F, Cl, CN, OMe or CF3; R4 is H, SO2CF3, SO2CH3, CO2Me, COMe, CH2OCO-tertiary butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COMe, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary butyl or COSMe; and Rf is C1-C3 haloalkyl.

13. The compound of claim 12, all its stereoisomers, N-oxides or salts thereof, wherein Q is O or S; R7 is H; R8 is H; Rf is CF3; R9 and R10 together with the carbon atom to which they are attached form a 3 to 7-membered ring, which is a 5 or 6-membered ring; Rv is independently selected from the group consisting of: H, methyl, ethyl, propyl, cyclopropylmethyl, propyne, or cyanomethyl; and r is 1 or 2.

14. The compound of claim 13, all its stereoisomers, N-oxides or salts thereof, wherein R9 and R10 together with the carbon atom to which they are attached form cyclopentane, cyclohexane, tetrahydro-2H-piperanone or tetrahydro-2H-thiopiperanone; and Rv is H.

15. The compound of claim 12, all its stereoisomers, N-oxides or salts thereof, wherein Q is CR11R12; R7 is H; R8 is H; R9 is H; R10 is H; R11 and R12 together with the attached carbon atom form a fused 3 to 7-membered ring containing a carbon atom and any 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, the ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of: halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy; and Rf is CF3.

16. The compound of claim 15, all its stereoisomers, N-oxides or salts thereof, wherein R11 and R12 together with the attached carbon atom form a fused 3 to 7-membered ring, which is an unsubstituted 5 or 6-membered ring.

17. The compound of claim 1, all its stereoisomers, N-oxides or salts thereof, wherein G is G-3; R1 is C1-C7 alkyl, halogen or C3-C7 cycloalkyl; R2 is H, Me or F; R3 is H, Me, F, Cl, CN, OMe or CF3; R4 is H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tertiary butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary butyl or COSMe; R13 is C1-C7 alkyl; R14 is C1-C4 alkyl; R15 is H; and Rf is C1-C3 haloalkyl.

18. The compound of claim 1, all its stereoisomers, N-oxides or salts thereof, wherein G is G-4; R1 is a C1-C7 alkyl, halogen or C3-C7 cycloalkyl; R2 is H, Me or F; R3 is H, Me, F, Cl, CN, OMe or CF3; R4 is H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tert-butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary-butyl or COSMe; R13 is a C1-C7 alkyl; Rf is a C1-C3 haloalkyl; R15 is H, C1-C3 Alkyl or C1-C3 alkoxy; and R16 is H, cyano, C1-C4 alkyl, halogen, C1-C4 alkylthio, C1-C4 haloalkyl or C1-C4 alkoxy.

19. The compound of claim 1, all its stereoisomers, N-oxides or salts thereof, wherein G is G-5; R1 is a C1-C7 alkyl, halogen or C3-C7 cycloalkyl; R2 is H, Me or F; R3 is H, Me, F, Cl, CN, OMe or CF3; R4 is H, SO2CF3, SO2CH3, CO2Me, COME, CH2OCO-tertiary butyl, CH2OCO-n-butyl, CH2OCO-cyclohexyl, CH2OCO-cyclopentyl, CH2OCOCH2CH3, COME, CH2OCOPh, CH2OCO-isobutyl, CH2OCOMe, CH2OCO-secondary butyl or COSMe; Rf is a C1-C3 haloalkyl; R16 is H or C1-C4 alkyl; R17 is H, C1-C4 alkyl, halogen, or C1-C4 alkoxy; and R18 is H or C1-C3 alkoxy.

20. The compound of claim 1, all its stereoisomers, N-oxides or salts thereof, are selected from the group consisting of: N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 207); N-[2,4-dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoazol-3-yl]phenyl]-1,1,1-trifluoromethanesulfonamide (compound 103); N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 197); N-[2,4-dimethyl-5-(3a,4,7,7a-tetrahydro-5H-piperanyl[4,3-d]isoazol-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 121); N-[2,4-dimethyl-5-(3a,6,7,7a-tetrahydro-4H-piperanyl[3,4-d]isoazol-3-yl)phenyl]-1,1,1-trifluoromethanesulfonamide (compound 120); N-[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4,5]dec-2-yl)phenyl]-1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide (compound 267); 2,2-Dimethylpropionic acid [[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (compound 140); 2,2-Dimethylpropionic acid [[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (compound 159); 2,2-Dimethylpropionic acid [[2,4-dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoazol-3-yl]phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (compound 100); and 2,2-dimethylpropionic acid [[2,4-dimethyl-5-(1-sideoxy-2-azaspiro[4.5]dec-2-yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl ester (compound 268).

21. The compound of claim 1, all its stereoisomers, N-oxides or salts thereof, is: methyl 2,2-dimethylpropionic acid [[(trifluoromethyl)sulfonyl][2,3,4-trimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopenta[d]isoazol-3-yl]phenyl]amino]ester.

22. A herbicidal composition comprising the compound of claim 1, all its stereoisomers, N-oxides or salts thereof, and at least one component selected from the group consisting of: surfactants, solid diluents and liquid diluents.

23. A herbicidal composition comprising a compound as claimed in claim 1, all its stereoisomers, N-oxides or salts thereof; at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners; and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

24. A herbicidal mixture comprising (a) the compound of claim 1, all its stereoisomers, N-oxides or salts thereof, and (b) at least one additional active ingredient selected from: (b1) a photosystem II inhibitor, (b2) an acetylhydroxy acid synthase (AHAS) inhibitor, (b3) an acetyl-CoA carboxylase (ACCase) inhibitor, (b4) an auxin mimic, (b5) a 5-enol-acetylshikimate-3-phosphate (EPSP) synthase inhibitor, (b6) a system I electron diverter, (b7) a protoporphyrinogen oxidase (PPO) inhibitor, (b8) a glutamic acid synthase (GS) inhibitor, and (b9) a very long-chain fatty acid (VLCFA) elongation enzyme inhibitor. Formulations, (b10) auxin transport inhibitors, (b11) phytopenic lycopene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) melanoic acid solanyltransferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides, including mitotic disruptors, organoarsenic agents, succinate, brombutazone, cyclohexane, bensulfuron, meropenem, oat fusarium, tiamethoxam, ethoxybenzamide, succinate, phosmet, phosmet-ammonium, hydantoin, methyl tiamethoxam, oleic acid, succinate, nonanoic acid and barnyardgrass, (b16) herbicide safeners and salts of compounds (b1) to (b16).

25. A method for controlling the growth of unwanted vegetation, comprising contacting vegetation or the environment with a herbicidal amount of a compound as claimed in claim 1, all its stereoisomers, N-oxides or their salts.

26. The method of claim 25 further comprises, in an herbicidal effective amount, at least one selected from (b1) a photosystem II inhibitor, (b2) an acetylhydroxy acid synthase (AHAS) inhibitor, (b3) an acetyl-CoA carboxylase (ACCase) inhibitor, (b4) an auxin mimic, (b5) a 5-enol-acetylshikimate-3-phosphate (EPSP) synthase inhibitor, (b6) a system I electron diverter, (b7) a protoporphyrinogen oxidase (PPO) inhibitor, (b8) a glutamic acid synthase (GS) inhibitor, (b9) a very long chain fatty acid (VLCFA) elongation enzyme inhibitor, (b10) an auxin transport inhibitor, and (b11) an octahydrophenanthrene. Lycopene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) melanoic acid solanyltransferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides, including mitotic disruptors, organoarsenic agents, succinate, brombutazone, cyclohexane, bensulfuron, maloxane, oat fumonisin, tiamethoxam, ethoxybenzamide, phosmet, phosmet-ammonium, hydantoin, methyl tiamethoxam, oleic acid, succinate, nonanoic acid and barnyardgrass, (b16) additional active ingredients of herbicide safeners and salts of compounds (b1) to (b16) in contact with vegetation or its environment.