Substituted oxazolidinones and imidazolinones as herbicides

Abstract

A compound of formula 1, comprising all stereoisomers, N-oxides, and salts thereof, an agricultural composition containing the same, and its use as a herbicide are disclosed, wherein Z is optionally R 4 A group of five-membered rings, substituted by the following groups, selected from the group of fully saturated or fully or partially unsaturated rings shown below, and R, R 1 , R 2 , R 3 , R 4 , R 5 V, W, Y, Z, and n are as defined herein. [Formula 1] TIFF2026511091000164.tif58170

Description

[Technical Field]

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

[0002] Controlling undesirable vegetation is crucial for achieving high yield efficiency. In particular, selective control of weed growth in useful crops, especially rice, soybeans, sugar beets, maize, potatoes, wheat, barley, tomatoes, and plantation crops, is highly desirable. Failure to suppress weed growth in these useful crops can significantly reduce productivity, thereby increasing costs for consumers. Controlling undesirable vegetation in uncultivated land is also important. While many products are commercially available for these purposes, there is a continuous need for novel compounds that are more effective, less expensive, less toxic, more environmentally safe, or have different sites of action. [Overview of the Initiative] [Means for solving the problem]

[0003] The present invention relates to formula 1: [ka] (In the formula, Y is either O or NH. Z is arbitrarily R v The following groups of fully saturated or fully or partially unsaturated five-membered rings that are substituted by a group [ka] Selected from, m is 0, 1, or 2. R v Halogen, cyanoacrylate, CO2, 8or (C1-C2)-alkyl or (C1-C2)-alkoxy, each of which is substituted by n groups independently selected from the group consisting of halogen, Each R is independently H, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, S(O) p R 7 or CO2R 8 wherein, n is 0, 1, 2, 3, 4 or 5, p is 0, 1 or 2, V and W are each independently O or S, X is a direct bond, O, S or NR 6 wherein, R 1 and R 2 are each independently hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C6 cyanoalkoxy, R 3H, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C2-C5 alkenyloxy, C2-C5 alkynyloxy, C3-C7 cycloalkoxy, C3-C7 cycloalkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C6 haloalkyl, C2-C5 haloalkenyl, C2-C5 haloalkynyl, C2-C5 alkoxyalkyl, C2-C5 haloalkoxyalkyl, C1-C5 alkoxy, C1-C6 haloalkoxy, C1 ~C5 alkylthio, C1~C4 alkylsulfinyl, C1~C4 alkylsulfonyl, C1~C4 alkylsulfonate, C1~C4 haloalkylthio, C1~C4 haloalkylsulfinyl, C1~C4 haloalkylsulfonyl, or C2~C5 alkoxycarbonyl, each of which is optionally further substituted with at least one group from the group consisting of halogen, cyano, C1~C4 alkoxy, C1~C5 alkylthio, C1~C4 alkylsulfinyl, C1~C4 alkylsulfonyl, and hydroxyl. R 4 These are independently H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or W 1 G 1 And, W 1 These are direct bonds, C1-C4 alkanediyl or C1-C4 alkenediyl, G 1 is S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 or COR 12 And, R 5 H, C1~C 12 Alkyl, NH2, N=CR 8 R 12 , C3-C7 cycloalkyl, C3-C 12Cycloalkylalkyl, C2-C8 alkenyl, C5-C6 cycloalkenyl, C2-C8 alkynyl, (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR 12 Each of these is optionally substituted with one or more groups from the group consisting of halogens, cyanos, C1-C6 alkyls, C1-C6 alkoxys, hydroxyls, and aryls. q is 0, 1, 2, 3, 4, or 5. R 6 is hydrogen, cyano, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR 10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 , an optionally substituted aryl, an optionally substituted heteroaryl, or an optionally substituted heterocycline, R 6 C1~C 12 Alkyl, C3-C8 cycloalkyl, C4-C 12 Cycloalkylalkyl, C2~C 12 Alkenyl, C5-C7 cycloalkenyl or C2-C 12 These are alkynyls, and each of them is a halogen, cyano, nitro, OR 9 , S(O) p R7 、SO2NR 10 R 11 、CO2R 8 、CONR 10 R 11 、COR 12 、NR 10 R 11 、NR 10 COR 12 、NR 10 CONR 10 R 11 、NR 10 CO2R 8 、NR 10 SO2R 7 、NR 10 SO2NR 10 R 11 、C(R 7 )=NOR 9 、Optionally substituted by one or more groups from the group consisting of optionally substituted aryl, optionally substituted heteroaryl or optionally substituted heterocyclyl, or R 5 and R 6 together with the nitrogen atom to which they are attached can form a 3- to 7-membered ring containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, with a maximum of two carbon atom ring members independently selected from C(=O) and C(=S), and sulfur atom ring members selected from S, S(O) or S(O)2, said ring being halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, OR 9 、S(O)<00​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​7 , NR 10 SO2NR 10 R 11 and C(R 7 )=NOR 9 It is optionally substituted with at least one substituent independently selected from the group consisting of the following: R 7 , R 8 , R 9 , R 10 , R 11 and R 12 Each of these is independently H, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C3-C7 cycloalkyl, or aryl, and each of these is optionally substituted with one or more groups from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. This applies to the compound, all stereoisomers thereof, N-oxides and salts, agricultural compositions containing the same, and their use as herbicides.

[0004] More specifically, the present invention relates to the compound of Formula 1 (including all stereoisomers), its N-oxide, or salt. The present invention also relates to herbicidal compositions comprising the compound of the present invention (i.e., in an effective amount for herbicidal control) 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 the vegetation or its environment with an effective amount for herbicidal control of the compound of the present invention (for example, as a composition described herein).

[0005] The present invention also includes herbicide mixtures comprising (a) a compound selected from Formula 1, its N-oxide and salts, and (b) at least one additional active ingredient selected from (b1) to (b16) and salts of the compounds (b1) to (b16) described below. [Modes for carrying out the invention]

[0006] As used herein, the terms "comprising", "including", "containing", "having", "characterized by", or any other variations thereof are intended to cover non-exclusive inclusion, unless there are explicit limitations. For example, a composition, mixture, process or method that includes a list of components is not necessarily limited to only those components, and may include other components not explicitly listed or components inherent to such composition, mixture, process or method.

[0007] The transitional phrase "consisting of" excludes any unrecited component, step or ingredient. In the case of a claim, it will exclude the inclusion of materials other than those recited, except for ordinary impurities associated therewith. When the phrase "consisting of" is recited in the body of a claim rather than immediately following the preamble, only the components recited in the body are limited and other components are not excluded from the scope of the claim as a whole.

[0008] The transitional phrase "consisting essentially of" is used to define a composition or method that includes additional materials, steps, features, components or ingredients in addition to those literally disclosed, provided that these additional materials, steps, features, components or ingredients do not substantially affect the basic and novel features of the claimed invention. The term "consisting essentially of" lies between "comprising" and "consisting of".

[0009] It should be readily understood that when the applicants define the invention or a part thereof using an open-ended term such as "comprising", this description should be construed to cover such inventions that use the terms "consisting essentially of" or "consisting of" as well, unless otherwise specified.

[0010] Furthermore, unless explicitly stated otherwise, "or" means inclusive or not exclusive. For example, condition A or B is satisfied by any of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0011] Similarly, the indefinite articles “a” and “an” preceding any component or element of the present invention are intended to be non-limiting in terms of the number (i.e., frequency of occurrence) of that component or element. Therefore, “a” and “an” should be read as including one or at least one, and the singular form of a component or element also includes plurals unless it is meant that the number is clearly singular.

[0012] As used herein, the term “seedling,” whether alone or in combination with other words, refers to a young plant that has grown from the embryo of a seed.

[0013] As used herein, the term “broadleaf,” either alone or within a word such as “broadleaf weeds,” means dicotyledons or dicotyledonous plants, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.

[0014] As used herein, the term "alkylation" refers to a reaction in which a nucleophile replaces a carbon-containing group with a leaving group such as a halide or sulfonate. Unless otherwise specified, the term "alkylation" is not limited to alkyl groups.

[0015] In the above description, the term "alkyl," used alone or in compound terms such as "alkylthio" or "haloalkyl," includes linear or branched alkyls, e.g., methyl, ethyl, n-propyl, i-propyl, and various butyl, pentyl, or hexyl isomers. "Alkenyl" includes linear or branched alkenes, e.g., ethenyl, 1-propenyl, 2-propenyl, and different butenyl, pentenyl, and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes linear or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl, and different butynyl, pentynyl, and hexynyl isomers. "Alkynyl" may also include moieties composed of multiple triple bonds, such as 2,5-hexadienyl.

[0016] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, and different butoxy, pentoxy, and hexyloxy isomers. "Alkoxyalkyl" means that the alkyl group is substituted with an alkoxy group. Examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2, and CH3CH2OCH2CH2. "Hydroxyalkyl" means that the alkyl group is substituted with a hydroxyl group. "Hydroxycycloalkyl" means that the cycloalkyl group is substituted with a hydroxyl group. "Hydroxyhaloalkyl" means that the haloalkyl group is substituted with a hydroxyl group. "Alkoxycycloalkyl" means that the cycloalkyl group is substituted with an alkoxy group. "Alkoxyhaloalkyl" means that the haloalkyl group is substituted with an alkoxy group.

[0017] "Alkoxyalkoxy" means that the alkoxy is substituted with another alkoxy group. "Alkylthio" includes branched or linear alkylthio moieties, such as methylthio, ethylthio, and different propylthio, butylthio, pentylthio, and hexylthio isomers. "Alkylthioalkyl" means that the alkyl is substituted with another alkylthio group. Examples of "Alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2, and CH3CH2SCH2CH2. "Alkylsulfinyl" includes both enantiomers of the alkylsulfinyl group. Examples of "Alkylsulfinyl" include CH3S(O)-, CH3CH2S(O)-, CH3CH2CH2S(O)-, (CH3)2CHS(O)-, and different butylsulfinyl, pentylsulfinyl, and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and different butylsulfonyl, pentylsulfonyl, and hexylsulfonyl isomers. Examples of "alkylsulfonates" include CH3S(O)2O-, CH3CH2S(O)2O-, CH3CH2CH2S(O)2O-, (CH3)2CHS(O)2O-, and different butylsulfonate, pentylsulfonate, and hexylsulfonate isomers. "Cyanoalkyl" means an alkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH2 and NCCH2CH2 (represented instead as CH2CH2CN). "Nitroalkyl" means an alkyl group substituted with one nitro group. Examples of "nitroalkyl" include NO2NCH2 and NO2NCH2CH2 (sometimes represented as CH2CH2NO2). "Cyano" means NC-, and "formyl" means HC(=O)-. "Alkylamino" contains an NH group substituted with a linear or branched alkyl group. Examples of "alkylamino" include CH3CH2NH, CH3CH2CH2NH, and (CH3)2CHCH2NH.Examples of "dialkylamino" include (CH3)2N, (CH3CH2CH2)2N, and CH3CH2(CH3)N. "Alkylsili" contains a silyl group substituted with a linear or branched alkyl group. "Trialkylsili" contains three silyl groups substituted with linear or branched alkyl groups. Examples of "trialkylsili" include (CH3)3Si- and (CH3CH2)3Si-. "Trialkylserial quinyl" means that the alkynyl is substituted with a trialkylsili. Examples of "trialkylserial quinyl" include (CH3)3SiC≡C- and (CH3CH2)3SiC≡C-.

[0018] "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "cycloalkylalkyl" means that the alkyl portion is substituted with a cycloalkyl group. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl groups bonded to a linear or branched alkyl group. The term "alkylcycloalkyl" means that the alkyl group bonded to the cycloalkyl group. The term "cycloalkoxy" means that the cycloalkyl group is bonded via oxygen. Examples of "cycloalkoxy" include cyclopropoxy, cyclobutoxy, and cyclopentoxy. The term "cycloalkoxyalkyl" means that the alkyl portion is substituted with a cycloalkoxy group. Examples of "cycloalkoxyalkyl" include cyclopropoxymethyl, cyclobutoxyethyl, and cyclopentoxymethyl, and other cycloalkoxy groups bonded to a linear or branched alkyl group. "Oxacycloalkyl" represents a cycloalkyl group in which one ring member carbon is replaced by an oxygen atom. Examples of "oxacycloalkyl" include oxacyclopropyl, oxacyclobutyl, and oxacyclopentyl.

[0019] The term "halogen," when used alone, in a compound word such as "haloalkyl," or in a description such as "halogen-substituted alkyl," includes fluorine, chlorine, bromine, or iodine. Furthermore, when used in a compound word such as "haloalkyl" or in a description such as "halogen-substituted alkyl," the alkyl may be partially or completely substituted with the same or different halogen atoms. Examples of "haloalkyl" or "halogen-substituted alkyl" include F3C, ClCH2, CF3CH2, and CF3CCl2. The terms "haloalkoxy," "haloalkoxyalkyl," "haloalkylthio," "haloalkenyl," "haloalkynyl," "halocycloalkyl," "haloalkylcycloalkyl," "haloalkylsulfinyl," and "haloalkylsulfonyl" are defined similarly to the term "haloalkyl." Examples of "haloalkoxy" include CF3O-, CCl3CH2O-, HCF2CH2CH2O-, and CF3CH2O-. Examples of "haloalkoxyalkyls" include CF3OCH2-, CCl3CH2OCH2-, HCF2CH2CH2OCH2-, and CF3CH2OCH2-. Examples of "haloalkylthios" include CCl3S-, CF3S-, CCl3CH2S-, and ClCH2CH2CH2S-. Examples of "haloalkenyls" include (Cl)2C=CH-(Cl)2C=CHCH2- and CF3CH2CH=CHCH2-. Examples of "haloalkynyls" include HC≡CCHCl-, CF3C≡C-, CCl3C≡C-, and FCH2C≡CCH2-. Examples of "halocycloalkyls" include 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2-fluorocyclopropyl, 1-chlorocyclobutyl, 1-fluorocyclobutyl, and 2-fluorocyclobutyl. Examples of "haloalkylcycloalkyl" include 1-(chloromethyl)cyclopropyl, 2-(chloromethyl)cyclopropyl, 2-(fluoromethyl)cyclopropyl, 1-(chloromethyl)cyclobutyl, 2-(fluoroethyl)cyclobutyl, and 2-(fluoromethyl)cyclobutyl.

[0020] "Alkylcarbonyl" refers to a linear or branched alkyl moiety bonded to the C(=O) moiety. Examples of "alkylcarbonyl" include CH3C(=O)-, CH3CH2C(=O)-, CH3CH2CH2C(=O)-, (CH3)2CHC(=O)-, and different butoxy- or pentoxycarbonyl isomers. "Alkoxycarbonyl" refers to a linear or branched alkoxy moiety bonded to the C(=O) moiety. Examples of "alkoxycarbonyl" include CH3OC(=O)-, CH3CH2OC(=O)-, CH3CH2CH2OC(=O)-, (CH3)2CHOC(=O)-, and different butoxy- or pentoxycarbonyl isomers. C(=O) or C(O) indicates carbonyl. The term "alkoxycarbonylalkyl" refers to a linear or branched alkoxycarbonyl moiety bonded via the alkyl moiety. The term "alkylcarbonylalkyl" refers to a linear or branched alkylcarbonyl moiety bonded via an alkyl moiety. "Alkylcarbonyloxy" refers to an alkylcarbonyl moiety bonded via an oxygen bond. Examples of alkylcarbonyloxys include CH3C(=O)O-, CH3CH2C(=O)O-, CH3CH2CH2C(=O)O-, and (CH3)2CHC(=O)-. "Alkenyloxy" refers to an alkenyl moiety bonded via an oxygen bond. Examples of "alkenyloxys" include CH2CHCH2O-, 1-propenyloxy or CH3CHCHO-, 2-butenyloxy or CH3CHCHCH2O-, and different butenyloxy, pentenyloxy, and hexenyloxy isomers. The term "alkynyloxy" refers to an alkynyl moiety bonded via an oxygen bond. Examples of "alkenyloxys" may include multiple double bonds. Examples of "alkynyloxy" include CHCCH2O-, 1-propynyloxy or CH3CCO-, 2-butynyloxy or CH3CCCH2O-, and different butynyloxy, pentynyloxy, and hexynyloxy isomers. Examples of "alkynyloxy" may also include multiple triple bonds. The terms alkanediyl or alkenediyl refer to a straight-chain or branched-chain or alkene-linked-chain, respectively.Examples of alkanediyls include -CH2-, -CH2CH(CH3)-, or -CH2CH2CH2-. Examples of alkendiyls include -CH=CH-, -CH2C=CH-, or -CH=C(CH3)-. The term "adjacent" in relation to the arrangement of substituents means "next to" or "directly next to".

[0021] The total number of carbon atoms in a substituent is "C i ~C j These are indicated by the prefix "-", where i and j are numbers from 1 to 8. For example, C1-C4 alkylsulfonyls represent methylsulfonyl to butylsulfonyl, C3-C8 alkylcarbonylalkyls may be, for example, CH3COCH2-, CH3COCH2CH2- or CH3CH2CH2COCH2CH2CH2CH2-, C4-C7 alkylcycloalkyls may be, for example, methylcyclopropyl, methylcyclobutyl, ethylcyclopropyl, or propylcyclobutyl, C2 alkoxyalkyls represent CH3OCH2-, C3 alkoxyalkyls may be, for example, CH3CH(OCH3)-, CH3OCH2CH2- or CH3CH2OCH2-, and C4 alkoxyalkyls represent various isomers of alkyl groups substituted with alkoxy groups containing a total of four carbon atoms, examples of which include CH3CH2CH2OCH2- and CH3CH2OCH2CH2-.

[0022] Regarding the Z group, the arrow with a wavy line represents the bond to the C=W group in Equation 1, and Z is NR 4 Bonds that connect to are represented by solid lines with wavy lines. Several non-limiting examples can be found in Embodiment 2. Substituent R v The combination of Z and NR 4 The connections and arrows that link to each other are displayed without specifying the connection position. v , NR 4 The C=W group can be bonded to the Z ring by replacing a hydrogen atom via any of the available ring member carbons.

[0023] If a group contains a substituent that may be hydrogen, the presence of this substituent as hydrogen is understood to be equivalent to the group being unsubstituted. When one or more positions of a group are described as "unsubstituted" or "unsubstituted," the hydrogen atoms are bonded to occupy free valences. Unless otherwise specified that it is optionally substituted, the term "phenyl" means unsubstituted phenyl. Unless otherwise specified that it is optionally substituted, the term "benzyl" means unsubstituted benzyl.

[0024] If a compound is substituted with substituents having a subscript indicating that the number of substituents may be greater than one, then the substituents (if greater than one) are defined substituents, for example, (R) n (wherein n is 0, 1, 2, 3, or 4) is independently selected from the group. If n is 0, hydrogen may be located at that position even if not specified in the definition of substituents. If a functional group or compound is indicated to be optionally substituted by substituents, then the functional group or compound is unsubstituted or substituted. If one or more positions of a group are stated to be "unsubstituted" or "unsubstituted", then the hydrogen atom is bonded so as to occupy a free valence. If the variable element is H and this H is substituted by some group, then this means that the H is replaced by this group. For example, "R 3 If is H and is further optionally substituted with a halogen, then this is R 3 This means that it is H or a halogen.

[0025] The term "ring system" refers to a fused ring of two or more rings. The term "biring system" refers to a ring system consisting of two fused rings.

[0026] The compounds of the present invention may exist as one or more stereoisomers. These stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. Stereoiomers are isomers that have the same composition but differ in the spatial arrangement of atoms, and include enantiomers, diastereomers, cis-trans isomers (also known as geometric isomers), and atropisomers. Atropisomers arise from rotational constraints around a single bond, and the rotational barrier is high enough to allow for the isolation of the isomeric species. Those skilled in the art will understand that if one stereoisomer is enriched with respect to or separated from other stereoisomers, it may exhibit higher activity and / or beneficial effects. Furthermore, those skilled in the art know how to separate, enrich, and / or selectively prepare such stereoisomers. The compounds of the present invention may exist as mixtures of stereoisomers, individual stereoisomers, or in optically active forms.

[0027] Compounds of formula 1 typically exist in multiple forms; therefore, formula 1 encompasses all crystalline and amorphous forms exhibited by the compound. Amorphous forms include embodiments that are waxy and rubbery solids, as well as liquid embodiments such as solutions and melts. Crystalline forms include embodiments that are essentially single-crystal and embodiments that are mixtures of polymorphs (i.e., different crystal forms). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize into different crystalline forms, these forms differing in the arrangement and / or conformation of molecules within the crystal lattice. Polymorphs may have the same chemical composition, but their composition may differ due to the presence or absence of co-crystallized water or other molecules that may be weakly or strongly bonded within the lattice. Polymorphs may differ in chemical, physical, and biological properties such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspension, dissolution rate, and bioavailability. Those skilled in the art will understand that polymorphs of compounds of formula 1 may exhibit beneficial effects (e.g., suitability for preparing useful formulations, improved biological performance) compared to other polymorphs or polymorphic mixtures of the same compound of formula 1. The preparation and isolation of specific polymorphs of compounds of formula 1 can be achieved by methods known to those skilled in the art, such as crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism, see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

[0028] Those skilled in the art will understand that not all nitrogen-containing heterocycles can form N-oxides, as nitrogen must have available lone pairs of electrons to oxidize to an oxide, and will be able to identify nitrogen-containing heterocycles that can form N-oxides. Those skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for preparing N-oxides of heterocycles and tertiary amines are very well known to those skilled in the art and include oxidation of heterocycles and tertiary amines with peracids such as peracetic acid and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, and dioxiranes such as sodium perborate and dimethyldioxirane. These methods for preparing N-oxides are widely described and outlined in the literature. For example, TLGilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, SV Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A J Boulton and A. McKillop, Eds., Pergamon Press; Chemistry,vol.43,pp149-161,ARKatritzky,Ed.,Academic Press;M.Tisler and B.Stanovnik in Advances in Heterocyclic Chemistry,vol.9,pp285-291,ARKatritzky and AJBoulton,Eds.,Academic Press and GWHCheeseman and ESGWerstiuk in Advances in Heterocyclic See Chemistry, vol.22, pp390-392, ARKatritzky and AJBoulton, Eds., Academic Press.

[0029] Those skilled in the art recognize that salts of compounds and their corresponding non-salt forms reach an equilibrium in an environment and physiological conditions, and thus the salts share the biological usefulness of the non-salt form. Therefore, various salts of the compound of Formula 1 are useful for controlling undesirable vegetation (i.e., agriculturally suitable). Salts of the compound of Formula 1 include acid addition salts formed by adding 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. When the compound of Formula 1 contains an acidic moiety, the salts include those formed together with organic or inorganic salts such as pyridine, triethylamine, or ammonia, or amides, hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium, or barium. Therefore, the present invention includes compounds selected from Formula 1, its N-oxide, and agriculturally suitable salts.

[0030] In the art, various synthetic methods capable of preparing aromatic and non-aromatic heterocycles and ring systems are known. For a comprehensive review, see Comprehensive Heterocyclic Chemistry, A.R. Katritzky and C.W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 (8 volumes in total) and Comprehensive Heterocyclic Chemistry II, A.R. Katritzky, C.W. Rees and E.F.V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996 (12 volumes in total).

[0031] The embodiments of the present invention described in the summary of the invention include those described below. In the following embodiments, Formula 1 includes its stereoisomers, N-oxides, and salts. When referring to "the compound of Formula 1", the definition of the substituents defined in the summary of the invention is included unless further defined in the embodiments.

[0032] Embodiment 1. The compound of Formula 1 described in the summary of this disclosure, its stereoisomers, N-oxides and salts, agricultural compositions containing the same, and its use as a herbicide. Z Embodiment 2. A compound of Formula 1 or Embodiment 1, wherein ZA is selected from Z-1 to Z-29 shown below, ZB is selected from Z-30 to Z-62 shown below, ZC is selected from Z-63 to Z-64 shown below, and ZD is selected from Z-65 to Z-74 shown below. [ka] [ka] [ka] [ka] Embodiment 2a.Z is a compound of Embodiment 2, selected from the group ZA. Embodiment 2aa.Z is a compound of Embodiment 2a, selected from the group Z-1 to Z-12. Embodiment 2b.Z is the compound of Embodiment 2a, wherein Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24. Embodiment 2c.Z is a compound of Embodiment 2, selected from the group ZB. Embodiment 2d.Z is the compound of Embodiment 2b, which is Z-30, Z-34, Z-36, Z-42, Z-47, Z-48, Z-53, Z-54, Z-55, Z-57, or Z-62. Embodiment 2e.Z is the compound of Embodiment 2, wherein Z-1, Z-4, Z-22, or Z-30. Embodiment 2f.Z is the compound of Embodiment 2, wherein Z-63 or Z-64. Embodiment 2g.Z is the compound of Embodiment 2, where Z-65 to Z-74. m Embodiment 3.m is the compound of Embodiment 1, wherein m is 0 or 1. Embodiment 3a.m is the compound of Embodiment 3, wherein the compound is 0. Embodiment 3b.m is the compound of Embodiment 3, which is 1. R Embodiment 4. The compound of Embodiment 2, wherein R is independently H, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy. Embodiment 4a.R is the compound of Embodiment 4, independently of H, F, Cl, Br, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, or C1-C2 haloalkoxy. Embodiment 4b.R is the compound of Embodiment 4a, independently of H, F, Cl, Me, CF3, OMe, or OCF3. Embodiment 4c.R is the compound of Embodiment 4, independently being a halogen. Embodiment 4d.R is the compound of Embodiment 4c, independently of F or Cl. Embodiment 4e.R is the compound of Embodiment 4, with positions 3 and 5. n Embodiment 5a.n is the compound of Embodiment 2, which is 1, 2, 3, or 4. Embodiment 5b.n is the compound of Embodiment 5a, which is 1, 2, or 3. Embodiment 5c.n is the compound of Embodiment 5b, which is 1 or 2. Embodiment 5d.n is compound 2 of Embodiment 5c. p Embodiment 6a.n is the compound of Embodiment 2, wherein the compound is 0. Embodiment 6b.n is the compound of Embodiment 2, which is 1. Embodiment 6c.n is the compound of Embodiment 2, wherein the compound is 2. V and W Embodiment 7. The compound of Embodiment 2, wherein V and W are independently O or S. Embodiment 7a. The compound of Embodiment 7, wherein both V and W are O. X Embodiment 8a.X is the compound of Embodiment 2, wherein the bond is directly between O or S. Embodiment 8aa.X is the compound of Embodiment 8a, wherein the compound is O or S. Embodiment 8b.X is the compound of Embodiment 8a, which is directly bonded. Embodiment 8c.X is the compound of Embodiment 8a, wherein O is present. Embodiment 8d.X is the compound of Embodiment 8a, wherein S is present. Embodiment 8e.X is NR 6 The compound of Embodiment 2. R 1 and R 2 Embodiment 9.R 1 and R 2 The compound of Embodiment 2, wherein each of the elements is independently hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C6 cyanoalkoxy. Embodiment 9a.R 1 and R 2 The compound of Embodiment 9, wherein each is independently hydrogen, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or C1-C3 cyanoalkoxy. Embodiment 9b.R 1 and R 2 The compound of Embodiment 9a, wherein each is independently hydrogen, halogen, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 cyanoalkyl, C1-C2 alkoxy, C1-C2 haloalkoxy, or C1-C2 cyanoalkoxy. Embodiment 9c.R 1 and R 2 The compound of Embodiment 9b, wherein each is independently hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN. Embodiment 9d.R 1 and R 2 The compound of Embodiment 9, wherein each is independently hydrogen, halogen, or cyano. Embodiment 9e.R 1 and R 2 The compound of Embodiment 9d, wherein each is independently hydrogen, F, Cl, Br, or cyano. Embodiment 9f.R1 and R 2 The compound of Embodiment 9c, wherein each is independently hydrogen or Me. Embodiment 9g.R 1 and R 2 The compound of embodiment 9f, in which both are hydrogen. R 3 Embodiment 10.R 3 H, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C2-C5 alkenyloxy, C2-C5 alkynyloxy, C3-C7 cycloalkoxy, C3-C7 cycloalkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C6 haloalkyl, C2-C5 haloalkenyl, C2-C5 haloalkynyl, C2-C5 alkoxyalkyl, C2-C5 haloalkoxyalkyl, C1-C5 alkoxy, C1-C6 haloalkoxy, C1-C5 alkoxy The compound of Embodiment 2 is a carboxylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonate, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, or C2-C5 alkoxycarbonyl, each of which is optionally further substituted with at least one group from the group consisting of halogen, cyano, C1-C4 alkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, and hydroxyl. Embodiment 10a.R 3The compound of Embodiment 10 is H, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C2-C5 alkenyloxy, C2-C5 alkynyloxy, C3-C7 cycloalkoxy, C3-C7 cycloalkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C6 haloalkyl, C2-C5 haloalkenyl, C2-C5 haloalkynyl, C2-C5 alkoxyalkyl, C2-C5 haloalkoxyalkyl, C1-C5 alkoxy, C1-C6 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, or C1-C4 alkylsulfonyl. Embodiment 10b.R 3 The compound of Embodiment 10a is H, halogen, cyano, hydroxy, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkoxy, C3-C5 cycloalkoxyalkyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, or C1-C3 alkylsulfonyl. Embodiment 10c.R 3 The compound of Embodiment 10b is H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy. Embodiment 10d.R 3 The compound of Embodiment 10c is H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethyl, CF3, OMe, or OCF3. Embodiment 10e.R 3 The compound of Embodiment 10d is H, Me, Et, CH=CH2, C≡CH, cyclopropyl, CF3, OMe, or OCF3. Embodiment 10f.R 3The compound of Embodiment 10e, wherein is H, Me, Et, CH=CH2, C≡CH, cyclopropyl, CF3, OMe, or OCF3. Embodiment 10g.R 3 The compound of embodiment 10f is Me. R 4 Embodiment 11.R 4 The compound of Embodiment 2 is H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy. Embodiment 11a.R 4 The compound of Embodiment 11, wherein H is present. R 5 Embodiment 12.R 5 H, C1~C 12 Alkyl, NH2, N=CR 8 R 12 , C3-C7 cycloalkyl, C3-C 12 Cycloalkylalkyl, C2-C8 alkenyl, C5-C6 cycloalkenyl, C2-C8 alkynyl, (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR 12 The compound of Embodiment 2, wherein each of these is optionally substituted with one or more groups from the group consisting of halogens, cyanos, C1-C6 alkyls, C1-C6 alkoxys, hydroxyls, and aryls. Embodiment 12a.R 5 (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR 12The compounds of Embodiment 12, wherein each of these is optionally substituted with one or more groups from the group consisting of halogens, cyanos, C1-C3 alkyls, C1-C3 alkoxys, hydroxyls, and aryls. Embodiment 12b.R 5 (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR 12 The compound of Embodiment 12, wherein each of these is optionally substituted with one or more groups from the group consisting of F, Cl, cyano, C1-C3 alkyl, C1-C3 alkoxy, hydroxy, and aryl. Embodiment 12c.R 5 is H, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2) q S(O) p Me, (CH2) q OMe, (CH2) q The compound of Embodiment 12b, wherein each of these is COMe, and each of these is optionally substituted with one or more groups from the group consisting of F, Cl, cyano, C1-C3 alkyl, C1-C3 alkoxy, hydroxy, and Ph. Embodiment 12d.R 5 The compound of Embodiment 12c is H, Me, Et, i-pr, i-Bu, t-Bu, c-Pent, OMe, CH2CF3, CH2CN, (CH2)2OMe, CH2CO2Me, CH2CO2Et, CH2CO2(4-F-Ph), CH2SMe, CH2Ph, NCHHPh, (CH2)2SO2Me, SO2Me, SO2Et, SO2(n-Pr), SO2(c-Pr), SO2(t-Bu), SO2CF3, or SO2Ph. R 6 Embodiment 13.R 6 H, cyano, OR 9 S(O)pR 7 SO2NR 10 R 11 CO2R8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR 10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 , an optionally substituted aryl, an optionally substituted heteroaryl, or an optionally substituted heterocycline, R 6 C1~C 12 Alkyl, C3-C8 cycloalkyl, C4-C 12 Cycloalkylalkyl, C2~C 12 Alkenyl, C5-C7 cycloalkenyl or C2-C 12 These are alkynyls, and each of them is a halogen, cyano, nitro, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR 10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9, or, optionally substituted with one or more groups from the group consisting of optionally substituted aryls, optionally substituted heteroaryls, or optionally substituted heterocyclines, R 5 and R 6 These, together with the nitrogen atom to which they are bonded, can form a 3-7 membered ring containing a carbon atom and optionally 1-3 oxygen, sulfur, or nitrogen atoms as ring members, up to two carbon atom ring members independently selected from C(=O) and C(=S), and the sulfur atom ring member selected from S, S(O) or S(O)2, and the ring can be halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR 10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 The compound of Embodiment 2, which is optionally substituted with at least one substituent independently selected from the group consisting of . Embodiment 13a.R 6 H, cyano, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 Or C1~C 12 Alkyl, C3-C8 cycloalkyl, C4-C 12 Cycloalkylalkyl, C2~C 12 Alkenyls, C5-C7 cycloalkenyls, or C2-C7 12 These are alkynyls, and each of them is a halogen, cyano, nitro, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR 10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 The compound of Embodiment 13, which is optionally substituted with one or more substituents from the group consisting of the following. Embodiment 13aa.R 6 H, cyano, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11COR 12 , NR 10 R 11 , NR 10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 Alternatively, the compound of Embodiment 13a, which is Me, Et, c-Pr, CH2-c-Pr, CH2CH=CH2, or CH2C≡CH. Embodiment 13b.R 6 H, cyano, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 or COR 12 The compound of embodiment 13a. Embodiment 13c.R 6 These are C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C2-C4 alkenyl, C5-C7 cycloalkenyl, or C2-C6 alkynyl, each of which is a halogen, cyano, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 or NR 10 COR 12 The compound of Embodiment 13a, which is optionally substituted with one or more substituents from the group consisting of the following. Embodiment 13d.R 6 H, OR 9 , S(O) p R7 SO2NR 10 R 11 CO2R 8 or COR 12 The compound of embodiment 13b. Embodiment 13e.R 6 The compound of Embodiment 13c is a C1-C4 alkyl, C3-C8 cycloalkyl, C4-C8 cycloalkylalkyl, C2-C4 alkenyl, C5-C7 cycloalkenyl, or C2-C6 alkynyl. Embodiment 13f.R 6 H, OR 9 or S(O) p R 7 The compound of embodiment 13d. Embodiment 13g.R 6 The compound of Embodiment 13e is a C1-C4 alkyl or C3-C8 cycloalkyl compound. Embodiment 13h.R 6 is H, OMe, or S(O)2R 7 The compound of embodiment 13d. Embodiment 13i.R 6 The compound of Embodiment 13e is Me or c-pr. Embodiment 13j.R 5 and R 6 These, together with the nitrogen atom to which they are bonded, can form a 3-7 membered ring containing a carbon atom and optionally 1-3 oxygen, sulfur, or nitrogen atoms as ring members, where up to 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, and the ring can be halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, oxo, OR 9 S(O)pR 7 CO2R 8 or NR 10 R 11 The compound of Embodiment 13, which is optionally substituted by at least one substituent independently selected from the group consisting of . Embodiment 13: The k.3-7 membered ring comprises a carbon atom and optionally one or two oxygen, sulfur, or nitrogen atoms as ring members, where up to 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, and the ring is a halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, oxo, OR 9 , S(O) p R 7 CO2R 8 or NR 10 R 11 The compound of Embodiment 13j, which is optionally substituted by at least one substituent independently selected from the group consisting of . Embodiment 13k: A compound of Embodiment 13k in which a 3- to 7-membered ring comprises a carbon atom and optionally 1 to 2 oxygen, sulfur, or nitrogen atoms as ring members, the maximum of 2 carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being selected from S, S(O), or S(O)2, and the ring being optionally substituted with at least one substituent independently selected from the group consisting of halogens, cyano, C1-C3 alkyl, and C1-C3 haloalkyl. Embodiment 13m. The compound of Embodiment 13l, wherein the 3- to 7-membered ring is selected from the group consisting of morpholinyl, thiomorpholinyl, oxazinyl, thiadinyl, piperidinyl, piperazinyl and their isomers, and the ring is optionally substituted with at least one substituent independently selected from the group consisting of halogens, cyano, C1-C3 alkyl and C1-C3 haloalkyl. R 7 , R 8 , R 9 , R 10 , R 11 and R 12 Embodiment 14.R 7 , R 8 , R 9 , R 10 , R 11 and R 12The compound of Embodiment 2, wherein each of the elements is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, or aryl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, and aryl. Embodiment 14a.R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The compound of Embodiment 14, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or aryl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, and aryl. Embodiment 14b.R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The compound of Embodiment 14, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, and aryl. Embodiment 14c.R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The compound of Embodiment 14, wherein each of the following is independently H, Me, Et, Pr, i-pr, c-pr, t-Bu, CF3, OMe, OEt, CF3, CH2CF3, c-Pr, and Ph, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxys, and aryls. The compound of Formula 1 or Embodiment 1, wherein the stereochemical configuration of the carbon atom designated as Embodiment 15a.* is (1') shown below as Formula 1'. [ka] The compound of Formula 1 or the embodiment, wherein the stereochemical configuration of the carbon atom designated as Embodiment 15b.* is (1'') shown below as Formula 1''. [ka] The compound of Formula 1 or Embodiment 1, wherein the stereochemical configuration of the carbon atoms designated as Embodiment 15c.* is a racemate shown below as Formula 1. [ka]

[0033] The embodiments of the present invention, including the above embodiments 1 to 14c and any other embodiments described herein, may be combined in any way, and the description of the variable elements of the embodiments relates not only to the compounds of Formula 1 but also to starting compounds and intermediate compounds useful for the preparation of the compounds of Formula 1. Furthermore, the embodiments of the present invention, including the above embodiments 1 to 14c and any other embodiments described herein, and any combination thereof, also relate to the compositions and methods of the present invention.

[0034] The following are examples of combinations of embodiments 1 to 14c: Embodiment AZ-A is selected from Z-1 to Z-29, ZB is selected from Z-30 to Z-62, ZC is selected from Z-63 to Z-64, and ZD is selected from Z-65 to Z-74. [ka] [ka] [ka] [ka] Selected from, m is either 0 or 1. R is independently H, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy. n is 1, 2, or 3. R 1 and R 2 Each of these is independently hydrogen, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or C1-C3 cyanoalkoxy. R 3 The compound of Formula 1 or Embodiment 1 is a compound of Formula 1 or Embodiment 1, wherein is H, halogen, cyano, hydroxy, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkoxyalkyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, or C1-C3 alkylsulfonyl. Embodiment A1.Z is selected from the group ZA, R is independently H, F, Cl, Br, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, or C1-C2 haloalkoxy. Both V and W are O. X is either O or S, R 3 These are H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 4 These are H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 5 H, C1~C 12 Alkyl, NH2, N=CR8 R 12 , C3-C7 cycloalkyl, C3-C 12 Cycloalkylalkyl, C2-C8 alkenyl, C5-C6 cycloalkenyl, C2-C8 alkynyl, (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR 12 The compound of Embodiment A, wherein each of these is optionally substituted with one or more groups from the group consisting of halogens, cyanos, C1-C6 alkyls, C1-C6 alkoxys, hydroxyls, and aryls. Embodiment A2.Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24, R is independently H, F, Cl, Me, CF3, OMe, or OCF3. n is 2, R is in 3rd and 5th place. R 1 and R 2 These are, independently, hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN, R 3 These are H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethyl, CF3, OMe, or OCF3. R 5 is H, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2) q S(O) p Me, (CH2) q OMe, (CH2) q COMe is a compound, and each of these is optionally substituted with one or more groups from the group consisting of F, Cl, cyano, C1-C3 alkyl, C1-C3 alkoxy, hydroxy, and Ph. R 7 , R 8 , R 9 , R 10 , R 11 and R 12The compound of Embodiment A1, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. Embodiment A3.Z is selected from the group ZA, R is independently H, F, Cl, Br, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, or C1-C2 haloalkoxy. Both V and W are O. X is NR 6 And, R 3 These are H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 4 The compound of Embodiment A is H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy. Embodiment A4.Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24, R is independently H, F, Cl, Me, CF3, OMe, or OCF3. n is 2, R is in 3rd and 5th place. R 1 and R 2 These are, independently, hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN, R 3 These are H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethyl, CF3, OMe, or OCF3. R 7 , R 8 , R 9 , R 10 , R 11and R 12 The compound of Embodiment A3, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. Embodiment A5.R 5 and R 6 The compounds of Embodiment A3, wherein these atoms, together with the nitrogen atoms to which they are bonded, can form a 3- to 7-membered ring, the 3- to 7-membered ring containing a carbon atom and optionally 1-2 oxygen, sulfur, or nitrogen atoms as ring members, the maximum of 2 carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being selected from S, S(O), or S(O)2, and the ring being optionally substituted with at least one substituent independently selected from the group consisting of halogens, cyano, C1-C3 alkyl, and C1-C3 haloalkyl. Embodiment A6.Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24, R is independently H, F, Cl, Me, CF3, OMe, or OCF3. n is 2, R is in 3rd and 5th place. R 1 and R 2 These are, independently, hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN, R 3 These are H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethyl, CF3, OMe, or OCF3. R 7 , R 8 , R 9 , R 10 , R 11 and R 12The compound of Embodiment A5, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. Embodiment B1.Z is selected from the group ZB, R is independently H, F, Cl, Br, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, or C1-C2 haloalkoxy. Both V and W are O. X is either O or S, R 3 These are H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 4 These are H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 5 H, C1~C 12 Alkyl, NH2, N=CR 8 R 12 , C3-C7 cycloalkyl, C3-C 12 Cycloalkylalkyl, C2-C8 alkenyl, C5-C6 cycloalkenyl, C2-C8 alkynyl, (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR 12 The compound of Embodiment A, wherein each of these is optionally substituted with one or more groups from the group consisting of halogens, cyanos, C1-C6 alkyls, C1-C6 alkoxys, hydroxyls, and aryls. Embodiment B2.Z is Z-30, Z-34, Z-36, Z-42, Z-47, Z-48, Z-53, Z-54, Z-55, Z-57, or Z-62. R is independently H, F, Cl, Me, CF3, OMe, or OCF3. n is 2, R is in 3rd and 5th place. R 1 and R 2 These are, independently, hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN, R 3 These are H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethyl, CF3, OMe, or OCF3. R 5 is H, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2) q S(O) p Me, (CH2) q OMe, (CH2) q COMe is a compound, and each of these is optionally substituted with one or more groups from the group consisting of F, Cl, cyano, C1-C3 alkyl, C1-C3 alkoxy, hydroxy, and Ph. R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The compound of Embodiment B1, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, or aryl.

[0035] Specific embodiments include compounds of Formula 1 selected from the following group: (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2,2,2-trifluoroethyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2,2,2-trifluoroethyl, (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl, (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid 1-methylethyl, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate methyl, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-methylpropyl, (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid, and (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate ethyl.

[0036] Specific embodiments include compounds of Formula 1 selected from the group consisting of: compound numbers 89, 96, 98, 128, 130, 140, 145, 161, 164, and 169.

[0037] The combinations of embodiments 1 to 14c are illustrated in the following embodiments P1 to P15: Embodiment P1. Formula 1A: [ka] (In the formula, Z is arbitrarily R 4 The following groups of fully saturated or fully or partially unsaturated five-membered rings that are substituted by a group [ka] Selected from, m is 0, 1, or 2. Each R independently represents H, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C7 cycloalkyl, C3-C7 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or S(O). p R 7 or CO2R 8 And, n is 0, 1, 2, 3, 4, or 5. p is 0, 1, or 2. V and W are independently either O or S. X is a direct bond, O, S, or NR 6 And, R 1 and R 2 Each of these is independently hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C6 cyanoalkoxy. R 3 H, halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C2-C5 alkenyloxy, C2-C5 alkynyloxy, C3-C7 cycloalkoxy, C3-C7 cycloalkoxyalkyl, C3-C6 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C6 haloalkyl, C2-C5 haloalkenyl, C2-C5 haloalkynyl, C2-C5 alkoxyalkyl, C2-C5 haloalkoxyalkyl, C1-C5 alkoxy, C1-C6 haloalkoxy, C1 ~C5 alkylthio, C1~C4 alkylsulfinyl, C1~C4 alkylsulfonyl, C1~C4 alkylsulfonate, C1~C4 haloalkylthio, C1~C4 haloalkylsulfinyl, C1~C4 haloalkylsulfonyl, or C2~C5 alkoxycarbonyl, each of which is optionally further substituted with at least one group from the group consisting of halogen, cyano, C1~C4 alkoxy, C1~C5 alkylthio, C1~C4 alkylsulfinyl, C1~C4 alkylsulfonyl, and hydroxyl. R 4 These are independently H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or W 1 G 1 And, W 1 These are direct bonds, C1-C4 alkanediyl or C1-C4 alkenediyl, G 1 is S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 or COR 12 And, R 5 H, C1~C 12 Alkyl, NH2, N=CR 8 R 12 , C3-C7 cycloalkyl, C3-C 12 Cycloalkylalkyl, C2-C8 alkenyl, C5-C6 cycloalkenyl, C2-C8 alkynyl, (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR 12 Each of these is optionally substituted with one or more groups from the group consisting of halogens, cyanos, C1-C6 alkyls, C1-C6 alkoxys, hydroxyls, and aryls. q is 0, 1, 2, 3, 4, or 5. R 6 is hydrogen, cyano, OR 9 , S(O) p R 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR 10 COR 12, NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 , an optionally substituted aryl, an optionally substituted heteroaryl, or an optionally substituted heterocycline, R 6 C1~C 12 Alkyl, C3-C8 cycloalkyl, C4-C 12 Cycloalkylalkyl, C2~C 12 Alkenyl, C5-C7 cycloalkenyl or C2-C 12 These are alkynyls, and each of them is a halogen, cyano, nitro, OR 9 S(O)pR 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR 10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 , or, optionally substituted with one or more groups from the group consisting of optionally substituted aryls, optionally substituted heteroaryls, or optionally substituted heterocyclines, R 5 and R 6These, together with the nitrogen atom to which they are bonded, can form a 3-7 membered ring containing a carbon atom and optionally 1-3 oxygen, sulfur, or nitrogen atoms as ring members, up to two carbon atom ring members independently selected from C(=O) and C(=S), and the sulfur atom ring member selected from S, S(O) or S(O)2, and the ring can be halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, OR 9 S(O)pR 7 SO2NR 10 R 11 CO2R 8 CONR 10 R 11 COR 12 , NR 10 R 11 , NR 10 COR 12 , NR 10 CONR 10 R 11 , NR 10 CO2R 8 , NR 10 SO2R 7 , NR 10 SO2NR 10 R 11 , C(R 7 )=NOR 9 It is optionally substituted with at least one substituent independently selected from the group consisting of the following: R 7 , R 8 , R 9 , R 10 , R 11 and R 12 Each of these is independently H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C7 cycloalkyl, or aryl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. Compounds of the same species, all of its stereoisomers, N-oxides, and salts. Embodiment P2.ZA is selected from Z-1 to Z-29, and ZB is selected from Z-30 to Z-62. [ka] [ka] [ka] Selected from, m is either 0 or 1. R is independently H, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy. n is 1, 2, or 3. R 1 and R 2 Each of these is independently hydrogen, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 cyanoalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or C1-C3 cyanoalkoxy. R 3 The compound of Embodiment P1 is H, halogen, cyano, hydroxy, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkoxy, C3-C5 cycloalkoxyalkyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 alkylsulfinyl, or C1-C3 alkylsulfonyl. Embodiment P3.Z is selected from the group ZA, R is independently H, F, Cl, Br, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, or C1-C2 haloalkoxy. Both V and W are O. X is either O or S, R 3These are H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 4 These are H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 5 H, C1~C 12 Alkyl, NH2, N=CR 8 R 12 , C3-C7 cycloalkyl, C3-C 12 Cycloalkylalkyl, C2-C8 alkenyl, C5-C6 cycloalkenyl, C2-C8 alkynyl, (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR 12 The compound of Embodiment P2, wherein each of these is optionally substituted with one or more groups from the group consisting of halogens, cyanos, C1-C6 alkyls, C1-C6 alkoxys, hydroxyls, and aryls. Embodiment P4.Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24, R is independently H, F, Cl, Me, CF3, OMe, or OCF3. n is 2, R is in 3rd and 5th place. R 1 and R 2 These are, independently, hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN, R 3 These are H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethic acid, CF3, OMe, or OCF3. R 5is H, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2) q S(O) p Me, (CH2) q OMe, (CH2) q COMe, each of which is optionally substituted with one or more groups from the group consisting of F, Cl, cyano, C1-C3 alkyl, C1-C3 alkoxy, hydroxy, and Ph, and R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The compound of Embodiment P3, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more groups from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. Embodiment P5.Z is selected from the group ZA, R is independently H, F, Cl, Br, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, or C1-C2 haloalkoxy. Both V and W are O. X is NR 6 And, R 3 These are H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 4 The compound of Embodiment P2 is H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy. Embodiment P6.Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24, R is independently H, F, Cl, Me, CF3, OMe, or OCF3. n is 2, R is in 3rd and 5th place. R 1 and R 2 These are, independently, hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN, R 3 These are H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethic acid, CF3, OMe, or OCF3. R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The compound of Embodiment P5, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. Embodiment P7.R 5 and R 6 The compounds of Embodiment P5, wherein these atoms can, together with the nitrogen atoms to which they are bonded, form a 3- to 7-membered ring, the 3- to 7-membered ring containing a carbon atom and optionally 1-2 oxygen, sulfur, or nitrogen atoms as ring members, the maximum of 2 carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being selected from S, S(O), or S(O)2, and the ring being optionally substituted with at least one substituent independently selected from the group consisting of halogens, cyano, C1-C3 alkyl, and C1-C3 haloalkyl. Embodiment P8.Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24, R is independently H, F, Cl, Me, CF3, OMe, or OCF3. n is 2, R is in 3rd and 5th place. R 1 and R 2 These are, independently, hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN, R 3These are H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethic acid, CF3, OMe, or OCF3. R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The compound of Embodiment P7, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. Embodiment P9.Z is selected from the group ZB, R is independently H, F, Cl, Br, cyano, C1-C2 alkyl, C1-C2 haloalkyl, C1-C2 alkoxy, or C1-C2 haloalkoxy. Both V and W are O. X is either O or S, R 3 These are H, C1-C3 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C3-C5 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C3 haloalkyl, C2-C3 alkoxyalkyl, C2-C3 haloalkoxyalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 4 These are H, C1-C6 alkyl, C3-C7 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy. R 5 H, C1~C 12 Alkyl, NH2, N=CR 8 R 12 , C3-C7 cycloalkyl, C3-C 12 Cycloalkylalkyl, C2-C8 alkenyl, C5-C6 cycloalkenyl, C2-C8 alkynyl, (CH2) q S(O) p R 7 , (CH2) q Ure 9 , (CH2) q COR12 The compound of Embodiment P2, wherein each of these is optionally substituted with one or more groups from the group consisting of halogens, cyanos, C1-C6 alkyls, C1-C6 alkoxys, hydroxyls, and aryls. Embodiment P10.Z is Z-30, Z-34, Z-36, Z-42, Z-47, Z-48, Z-53, Z-54, Z-55, Z-57, or Z-62, R is independently H, F, Cl, Me, CF3, OMe, or OCF3. n is 2, R is in 3rd and 5th place. R 1 and R 2 These are, independently, hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3, or OCH2CN, R 3 These are H, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethic acid, CF3, OMe, or OCF3. R 5 is H, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2) q S(O) p Me, (CH2) q OMe, (CH2) q COMe, each of which is optionally substituted with one or more groups from the group consisting of F, Cl, cyano, C1-C3 alkyl, C1-C3 alkoxy, hydroxy, and Ph. R 7 , R 8 , R 9 , R 10 , R 11 and R 12 The compound of Embodiment P9, wherein each of the elements is independently H, C1-C3 alkyl, C1-C3 haloalkyl, C3-C5 cycloalkyl, or phenyl, and each of these is optionally substituted with one or more substituents from the group consisting of F, Cl, C1-C2 alkoxy, or aryl. Embodiment P11. (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2,2,2-trifluoroethyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2,2,2-trifluoroethyl, (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl, (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid 1-methylethyl, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate methyl, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-methylpropyl, (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid, and (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate ethyl A compound of embodiment P1 1, selected from the group consisting of the following. Embodiment P12. A herbicide composition comprising the compound of Embodiment P1 and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents. Embodiment P13. A herbicide composition comprising the compound of Embodiment P1, at least one additional active ingredient selected from the group consisting of other herbicides and herbicide phytotoxicity reducers, and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents. Embodiment P14. (a) Compounds of Embodiment P1 and (b) (b1) Photosystem II inhibitor, (b2) Acetohydroxy acid synthase (AHAS) inhibitor, (b3) Acetyl-CoA carboxylase (ACCase) inhibitor, (b4) Auxin mimetic, (b5) 5-enolpyruvirshikimic acid-3-phosphate (EPSP) synthase inhibitor, (b6) Photosystem I electron converter, (b7) Protoporphyrinogen oxidase (PPO) inhibitor, (b8) Glutamine synthase (GS) inhibitor, (b9) Very long chain fatty acid (VLCFA) elongation enzyme inhibitor, (b10) Auxin transfer inhibitor, (b11) Phytoene desaturase (PDS) inhibitor, (b12) 4-Hydroxyphenylpyruvate dioxygenase (HPPD) A herbicide mixture comprising (b17) an inhibitor, (b13) a homogentisic acid soranesyltransferase (HST) inhibitor, (b14) a cellulose biosynthesis inhibitor, (b15) a dihydroorotic acid dehydrogenase (DHODH) inhibitor, (b16) a mitotic inhibitor, an organoarsenic compound, ashram, bromobutide, simmethyline, cumylon, dazomet, diphenzocort, dimuron, etobenzanide, flurenol, hosamin, hosamin-ammonium, hydantosaidin, metam, methyldimuron, oleic acid, oxadiclomefone, pelargonic acid and pyributicarb, (b17) a herbicide phytotoxicity reducer and at least one additional active ingredient selected from salts of compounds (b1) to (b17). Embodiment P15. A method for controlling the growth of undesirable vegetation, comprising contacting the vegetation or its environment with an effective amount of the compound of Embodiment P1 for weed control.

[0038] The present invention also relates to a method for controlling undesirable vegetation, comprising applying an effective herbicidal amount of the compound of the present invention (for example, as a composition described herein) to the habitat of the vegetation. Of note as embodiments of the method of use are those involving the compounds of the embodiments described above. The compounds of the present invention are particularly useful for selectively controlling weeds in crops such as wheat, barley, maize, soybeans, sunflowers, cotton, rapeseed, and rice, as well as specialty crops such as sugarcane, citrus fruits, fruits, and nuts.

[0039] Another embodiment worth noting is the herbicide composition of the present invention, which contains the compounds of the embodiments described above.

[0040] The present invention relates to (a) a compound selected from formula 1, its N-oxide and salt, and (b) (b1) a photosystem II inhibitor, (b2) an acetohydroxy acid synthase (AHAS) inhibitor, (b3) an acetyl-CoA carboxylase (ACCase) inhibitor, (b4) an auxin mimetic, (b5) a 5-enolpyruvirshikimic acid-3-phosphate (EPSP) synthase inhibitor, (b6) a photosystem I electron converter, (b7) a protoporphyrinogen oxidase (PPO) inhibitor, (b8) a glutamine synthase (GS) inhibitor, (b9) a very long-chain fatty acid (VLCFA) elongation enzyme inhibitor, (b10) an auxin transfer inhibitor, (b11) a phytoene desaturase (PDS) inhibitor, and (b12) a 4-hydroxyphenylpyruvate dioxygenase (HP (b17) Herbicide mixtures comprising (b17) herbicide phytotoxicity reducers and at least one additional active ingredient selected from salts of compounds (b1) to (b17).

[0041] "Photosystem II inhibitors" (b1) are Q B It binds to the D1 protein at the binding site, thereby enabling Q in chloroplast thylakoids. A From Q B It is a compound that inhibits electron transfer to photosystem II. Electrons blocked from passing through photosystem II are transferred to a series of reactions that disrupt the cell membrane, leading to chloroplast swelling, leakage from the membrane, and ultimately the formation of toxic compounds that cause cell destruction.B The binding site has three different sites. Binding site A binds to triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil; binding site B binds to phenylureas such as diurone; and binding site C binds to benzothiadiazoles such as bentazone, nitriles such as bromoxyn, and phenylpyridazines such as pyridate. Examples of photosystem II inhibitors include ametrine, amicarbazone, atrazine, bentazone, bromacil, bromophenoxime, bromoxyn, chlorbromulone, chloridazone, chlorotolurone, chloroxurone, cumilone, cyanazine, dimuron, desmedifam, desmethrin, dimeflon, dimethametrin, diurone, ethidimulone, fenuron, fluomethron, hexazinone, ioxynil, isoprotholone Examples include Isouron, Renasil, Linuron, Metamitron, Metabenzthiazulon, Metobromulone, Metoxron, Metrivudine, Monolinuron, Nevron, Pentanocrol, Fenmedifam, Prometon, Promethrin, Propanil, Propadin, Pyridafo, Piridate, Siderone, Simazine, Simetrin, Tebuthiurone, Terbasil, Terbumeton, Terbutyrazine, Terbutrin, and Trietadine.

[0042] "AHAS inhibitors" (b2) are compounds that kill plants by inhibiting acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), thereby inhibiting the production of branched-chain aliphatic amino acids such as valine, leucine, and isoleucine, which are necessary for protein synthesis and cell growth.Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac sodium salt, chloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, etamethosulfuron-methyl, ethoxysulfuron, flurazasulfuron, florasulam, flucarbazon sodium salt, flumetulam, flupyrusulfuron-methyl, flupyrusulfuron-sodium salt, horamsulfuron, halosulfuron-methyl, and imazametabenzme Chil, Imazamox, Imazapick, Imazapyr, Imazakine, Imazetapir, Imazosulfuron, Iodosulfuron Methyl (containing sodium salt), Iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)amino]carbonyl]benzenesulfonamide), Mesosulfuron Methyl), Metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazine-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl) [Amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), Methoslam, Methosulfuron methyl, Nicosulfuron, Oxasulfuron, Penoxslam, Primisulfuron methyl, Propoxycarbazone sodium salt, Propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), Prosulfuron, Pyrazosulfuron ethyl, Pyribenzoxime, Pyriphthalide, Pyrim Examples include Novac methyl, pyrithiobac sodium salt, limsulfuron, sulfomethane methyl, sulfosulfuron, thiencarbazone, thifensulfuron methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazine-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, trivenuron methyl, trifloxysulfuron (including sodium salt), triflusulfuron methyl, and tritosulfuron.

[0043] "ACCase inhibitors" (b3) are compounds that inhibit the acetyl-CoA carboxylase enzyme, which plays a role in catalyzing the initial stages of lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. When acetyl-CoA carboxylase is inhibited and subsequent lipid production ceases, the integrity of the cell membrane is impaired, especially in areas of active growth such as the growing point. Ultimately, the growth of new shoots and rhizomes stops, and the growing points of new shoots and rhizome buds begin to wither from the tip towards the base. Examples of ACCase inhibitors include alloxidime, butroxidime, cretodyme, clodinahop, cycloxidime, cyhalofop, diclohop, phenoxaprop, fluazihop, haloxyhop, pinoxadene, propoxoxidime, propaxafop, quizalohop, cethoxidime, tepraloxidime, and tralcoxidime, as well as optically resolved forms such as phenoxaprop-P, fluazihop-P, haloxyhop-P, and quizalohop-P, and ester forms such as clodinahoppropargyl, cyhalofopbutyl, diclohopmethyl, and phenoxaprop-P-ethyl.

[0044] Auxin is a plant hormone that regulates growth in many plant tissues. "Auxin mimetic" (b4) is a compound that mimics the plant growth hormone auxin, thereby disrupting the growth of sensitive plant species, causing uncontrolled and disordered growth, and ultimately leading to death. Examples of auxin mimetic include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)-2-pyridinecarboxylic acid 2-propyne-1-yl ester (CAS number: 2251111-17-6), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)-2-pyridinecarboxylic acid cyanomethyl ester (CAS number: 2251111-18-7), aminopyralide, benazoline ethyl, chloramben, crasiphos, Examples include clomeprop, clopyralide, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, harauxifene (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), harauxifene methyl (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid methyl), MCPA, MCPB, mecoprop, picloram, quinchlorac, kinmelac, 2,3,6-TBA, triclopyr, and 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid methyl.

[0045] "EPSP synthase inhibitors" (b5) are compounds that inhibit 5-enolpyruvirshikimicate-3-phosphate synthase, an enzyme involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan, and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant leaves and travel through the phloem to the growing point. Glyphosate belongs to this group and is a relatively unselective post-emergence herbicide. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium), and trimethium (another name for sulfosate) salts.

[0046] "Photosystem I electron converters" (b6) are compounds that accept electrons from Photosystem I and, through several cycles, generate hydroxyl radicals. These radicals are highly reactive and readily destroy unsaturated fatty acids such as membrane fatty acids and chlorophyll. This disrupts the integrity of the cell membrane, causing cells and organelles to "leak out," resulting in rapid wilting and drying of leaves, and ultimately leading to plant death. Examples of this second type of photosynthesis inhibitor include diquat, paraquat, and 1-(2-carboxyethyl)-4-(2-pyrimidinyl)pyridazinium (CAS number: 2285384-11-2).

[0047] "PPO inhibitors" (b7) are compounds that inhibit the enzyme protoporphyrinogen oxidase, resulting in the rapid production of highly reactive compounds in plants that rupture cell membranes and cause cell sap to leak out. Examples of PPO inhibitors include acifluorphen sodium salt, azaphenidine, benzfenzizone, bifenox, butafenacil, carfentrazone, carfentrazone ethyl, clomethoxyfen, 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazole carboxylate ethyl ester (CAS number: 1949837-17-5), synidone ethyl, fluazolate, flufenpyruethyl, flumicrolacpentyl, flumioxazine, fluoroglycofen ethyl, fluthiaset methyl, homesafen, halosaphen, lactofen, oxazial Examples include gil, oxadiazone, oxyflofen, pentoxazone, profluazole, pyraclonil, pyraflufenethyl, saflufenacil, sulfentrazone, tidiadimine, trifludimoxazine (dihydro-1,5-dimethyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyne-1-yl)-2H-1,4-benzoxazine-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione) and thiafenacil (N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate methyl).

[0048] "GS inhibitors" (b8) are compounds that inhibit the activity of glutamine synthase, an enzyme used by plants to convert ammonia into glutamine. As a result, ammonia accumulates and glutamine levels decrease. Plant damage is likely caused by a combination of ammonia toxicity and deficiency of amino acids necessary for other metabolic processes. Examples of GS inhibitors include glufosinate and its esters and salts, such as glufosinate ammonium salt and other phosphinotricin derivatives, such as glufosinate-P((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and viranaphos.

[0049] "VLCFA elongation enzyme inhibitors" (b9) are herbicides with diverse chemical structures that inhibit VLCFA elongation enzymes. VLCFA elongation enzymes are one of the enzymes involved in the biosynthesis of VLCFAs, located inside or near chloroplasts. Very long-chain fatty acids are major components of hydrophobic polymers in plants, preventing the drying of the leaf surface and providing stability to pollen grains. Examples of such herbicides include acetochlor, alachlor, anirophos, butachlor, cafenstrole, dimetachlor, dimethenamide, diphenamide, phenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanophan, mefenacet, metazochlor, metrachlor, naproanilide, napropamide, napropamide-M((2R)-N,N-diethyl-2-(1-naphthalenyloxy)propanamide), petoxamide, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and tenylchlor, as well as optically resolved forms such as S-methrachlor, chloroacetamide, and oxyacetamide.

[0050] Auxin transport inhibitors (b10) are chemical substances that inhibit auxin transport within plants by binding to proteins that transport auxin. Examples of auxin transport inhibitors include diflufenzopyr and naptalam (also known as N-(1-naphthyl)phthalamidic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid).

[0051] "PDS inhibitors" (b11) are compounds that inhibit the carotenoid biosynthesis pathway at the phytoene desaturation stage. Examples of PDS inhibitors include beflubutamide, diflufenican, flulidone, flurochloridone, flurutamon, norflurzone, and picolinafene.

[0052] HPPD inhibitors (b12) are chemicals that inhibit the biosynthesis of 4-hydroxyphenylpyruvate dioxygenase. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]octo-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), and flu Sulfinum, Iptriazopiride, Isoxachlortol, Isoxaflutol, Mesotrione, Pyrasulfol, Pyrazolinate, Pyrazoxiphen, Sulcotrione, Tefuryltrione, Tempotrione, Tolpyrate (1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazole-5-yl]oxy]ethylmethyl carbonate), Topramesone, 5-chloro-3-[(2-hydrox [C-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydroxy- Examples include 6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazole-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide, and 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazole-5-yl)-4-(trifluoromethyl)benzamide.

[0053] HST (homogentidic acid soranesyltransferase) inhibitors (b13) disrupt the plant's ability to convert homogentisic acid to 2-methyl-6-solanyl-1,4-benzoquinone, thereby inhibiting carotenoid biosynthesis. Examples of HST inhibitors include cyclopyrimolate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholine carboxylate), haloxydine, pyrichlor, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridine-2(1H)-one, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazine-6(5H)-one, and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.

[0054] HST inhibitors include formulas A and B: [ka] (In the formula, R d1 is H, Cl or CF3, and R d2 is H, Cl or Br, and R d3 is H or Cl, and R d4 is H, Cl or CF3, and R d5 is CH3, CH2CH3, or CH2CHF2, and R d6 OH or -OC(=O)-i-Pr, and R e1 is H, F, Cl, CH3 or CH2CH3, and R e2 is H or CF3, and R e3 is H, CH3 or CH2CH3, and R e4 is H, F, or Br, and R e5 is Cl, CH3, CF3, OCF3, or CH2CH3, and R e6 is H, CH3, CH2CHF2 or C≡CH, and R e7 These are OH, -OC(=O)Et, -OC(=O)-i-Pr, or -OC(=O)-t-Bu, and A e8 (This is N or CH) Other examples of compounds include the following.

[0055] "Cellulose biosynthesis inhibitors" (b14) inhibit cellulose biosynthesis in certain plants. They are most effective when applied to young plants or rapidly growing plants before or early after emergence. Examples of cellulose biosynthesis inhibitors include chlorthiamide, diclobenyl, flupoxam, and indadiphram (N 2 Examples include -[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben, and triaziphram.

[0056] "DHODH (dihydroorotic acid dehydrogenase) inhibitors" (b15) act by inhibiting the catalytic reaction of the fourth step in pyrimidine biosynthesis in plants. When pyrimidine biosynthesis is inhibited, plant growth stops. Examples of DHODH inhibitors include tetoflupyrrolimet ((3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide) and (3S,4R)-N-(2,3-difluorophenyl)-1-methyl-4-[1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl]-2-oxo-3-pyrrolidinecarboxamide.

[0057] "Other herbicides" (b16) include herbicides that act by various mechanisms of action, such as mitosis inhibitors (e.g., flamprop-M-methyl and flamprop-M-isopropyl), organoarsenic compounds (e.g., DSMA and MSMA), 7,8-dihydropteroic acid synthase inhibitors, chloroplast isoprenoid synthesis inhibitors, and cell wall biosynthesis inhibitors. Other herbicides include those whose mechanism of action is unknown, or which do not belong to the specific classifications described in (b1) to (b14), or which act through a combination of the mechanisms of action described above. Other examples of herbicides include acronifen, ashram, amitorol, bixzolon, broclozone, bromobutide, scinmethilin, cromazon, cumilon, dimuron, diphenzocoat, dimesulfazet, epiriphenacil, etobenzanide, fluomethron, flurenol, fosamine, fosamineammonium, dazomet, dimuron, ibuphencarbazone (1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carbazone Examples include ruboxamide, metam, methyl dimuron, oleic acid, oxadiclomefone, pelargonic acid, pyributicarb, 2,5-anhydro-3,4-dideoxy-4-[[[(5S)-3-(3,5-difluorophenyl)-5-ethenyl-4,5-dihydro-5-isoxazolyl]carbonyl]amino]threopentone methyl ester (CAS number: 27499989-21-6) and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole. Other herbicides (b16) include formula (b16A): [ka] (In the formula, R 12 These are H, C1-C6 alkyl, C1-C6 haloalkyl, or C4-C8 cycloalkyl. R 13 is H, C1-C6 alkyl or C1-C6 alkoxy, Q 1This is a ring system selected from the group consisting of phenyl, thienyl, pyridinyl, benzodioxolyl, naphthyl, naphthalenyl, benzofuranyl, furanyl, benzothiophenyl, and pyrazolyl, which are optionally substituted, and if the ring system is substituted, there are 1 to 3 R 14 It has been replaced with, Q 2 This is a ring system selected from the group consisting of phenyl, pyridinyl, benzodioxolyl, pyridinonyl, thiadiazolyl, thiazolyl, and oxazolyl, which are optionally substituted, and if the ring system is substituted, 1 to 3 R 15 It has been replaced with, Each R 14 These are independently halogens, C1-C6 alkyls, C1-C6 haloalkyls, C1-C6 alkoxys, C1-C6 haloalkoxys, C3-C8 sialoalkyls, cyanos, C1-C6 alkylthios, C1-C6 alkylsulfinyls, C1-C6 alkylsulfonyls, SF5, and NHR. 17 or 1 to 3 R's 16 Phenyl or 1-3 R atoms optionally substituted with 16で It is a pyrazolyl that has been optionally substituted, Each R 15 These are independently halogens, C1-C6 alkyls, C1-C6 haloalkyls, C1-C6 alkoxys, C1-C6 haloalkoxys, cyanos, nitros, C1-C6 alkylthios, C1-C6 alkylsulfinyls, and C1-C6 alkylsulfonyls. Each R 16 These are independently halogens, C1-C6 alkyls, or C1-C6 haloalkyls. R 17 (These are C1-C4 alkoxycarbonyl groups.) Other examples of compounds include the following.

[0058] In one embodiment, where "other herbicides" (b16) also includes a compound of formula (b16A), preferably, R 12 is H or C1-C6 alkyl, more preferably R 12 is H or methyl. Preferably, R 13 is H. Preferably, Q1 It is either a phenyl ring or a pyridinyl ring, and each ring has 1 to 3 R 14 It is replaced by, more preferably, Q 1 is 1-2 R 14 A phenyl ring substituted with Q. Preferably, Q 2 This is 1 to 3 R's 15 A phenyl ring substituted with, more preferably, Q 2 is 1-2 R 15 A phenyl ring substituted with R. Preferably, each R 14 R is independently a halogen, a C1-C4 alkyl, a C1-C3 haloalkyl, a C1-C3 alkoxy, or a C1-C3 haloalkoxy, and more preferably each R 14 These are independently chloro, fluoro, bromo, C1-C2 haloalkyl, C1-C2 haloalkoxy, or C1-C2 alkoxy. Preferably, each R 15 These are independently halogens, C1-C4 alkyls, and C1-C3 haloalkoxys, and more preferably each R 15 These are independently chloro, fluoro, bromo, C1-C2 haloalkyl, C1-C2 haloalkoxy, or C1-C2 alkoxy. Specifically preferred "other herbicides" (b16) include any one of the following (b16A-1) to (b16A-15).

[0059] [Table 1]

[0060] [Table 2]

[0061] [Table 3]

[0062] [Table 4]

[0063] Another embodiment of "other herbicides" (b16) is formula (b16C): [ka] (In the formula, R 1 is Cl, Br, or CN, and R 2 (This is C(=O)CH2CH2CF3, CH2CH2CH2CH2CF3, or 3-CHF2-isoxazole-5-yl) Other examples of compounds include the following.

[0064] A "herbicide phytotoxicity reducer" (b17) is a substance added to herbicide formulations to eliminate or reduce the phytotoxic effects of herbicides on specific crops. This compound protects crops from herbicide damage but does not typically interfere with the herbicide's control of undesirable vegetation. Examples of herbicide phytotoxicity reducers include, but are not limited to, benoxacol, cumilon, siomethrinil, cyprosulfamide, dimuron, dichlormid, dicyclonone, dietholate, dimepiperate, fenchlorazole ethyl, fenchlorim, flurazole, fluxofenim, flurazole, isoxadifen ethyl, mefenpyrdiethyl, mephenate, methoxyphenone, naphthalic anhydride, oxavethrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4(chloromethyl)sulfonylbenzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON Examples include 4660), 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide.

[0065] Preferably for better control of undesirable vegetation (e.g., by reducing the amount used due to greater efficacy than additive, a broader weed control spectrum, or higher safety for crops) or for preventing the emergence of resistant weeds, is the compound of the present invention and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)-2-pyridinecarboxylic acid 2-propyne-1-yl ester (CAS No.: 2251111-17-6), 4-amino-3-chloro-5-fluoro-6-(7- Luoro-1H-indole-6-yl)-2-pyridinecarboxylate cyanomethyl ester (CAS No.: 2251111-18-7), 2,5-anhydro-3,4-dideoxy-4-[[[(5S)-3-(3,5-difluorophenyl)-5-ethenyl-4,5-dihydro-5-isoxazolyl]carbonyl]amino]threopentone methyl ester (CAS No.: 27499989-21-6), atrazine, azimsulfuron, beflubutamide, beflubutamide-M, bixolone, bloclo Zon, benzisothiazolinone, 1-(2-carboxyethyl)-4-(2-pyrimidinyl)pyridazinium (CAS No.: 2285384-11-2) and its salts, carfentrazone-ethyl, chlorimuron-ethyl, 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazole carboxylate ethyl ester (CAS No.: 1949837-17 -5) Chlorsulfuron-methyl, Chromazon, clopyralidopotassium, chloransrum methyl, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethylisoxazolidinone, 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethylisoxazolidinone, etamethosulfuron-methyl, flumetulam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,A mixture with herbicides selected from the group consisting of 4H)-dione, flupyrsulfuron-methyl, fluthiaset-methyl, homesafen, imazetapyr, lenacil, mesotrione, metrivudine, metosulfuron-methyl, petoxamide, picloram, pyroxasulfone, quinchlorac, limsulfuron, S-methrachlor, sulfenthrazone, thifensulfuron-methyl, triflusulfuron-methyl, and trivenuron-methyl.

[0066] To prepare the compound of formula 1, one or more of the methods and variations described in schemes 1 to 5 below can be used. R, R in the compounds of formulas 1 to 8 below 1 , R 2 , R 3 , R 4 , R 5 The definitions of X, V, W, Z, and n are as defined above in the summary of the invention, unless otherwise specified. The compounds of formula 1a are part of the compounds of formula 1, and in this disclosure, including the scheme, the substituents of formula 1a are as defined in formula 1, unless otherwise specified.

[0067] As shown in Scheme 1, the compound of formula 1a (i.e., the compound of formula 1 where V is O) can be prepared by reacting the acid of formula 2 with the amine of formula 3 in the presence of a dehydration coupling reagent, such as propylphosphonic anhydride, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), benzotriazole-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP), N,N'-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, or 2-chloro-1-methylpyridinium iodide. This reaction is typically carried out at temperatures ranging from 0 to 60°C in solvents such as dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate, in the presence of bases such as triethylamine, N,N-diisopropylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene. For amide coupling conditions, see Org. Process Res. Dev. 2016, 20, 2, 140-177. [ka]

[0068] As shown in Scheme 2, the compound of formula 2 (wherein R' is a lower alkyl) can be prepared by hydrolyzing the ester of formula 4 under mild conditions. The hydrolysis is typically carried out in a solvent using a selective mild base. Suitable bases for this reaction include, but are not limited to, potassium trimethylsilanoate or trimethyltin oxide. A variety of cosolvents are suitable for this reaction, but are not limited to methanol, ethanol, and tetrahydrofuran. The reaction is carried out at temperatures ranging from -20°C to the boiling point of the solvent, usually in the range of 0 to 100°C. For detailed procedures, see Tetrahedron letter, 1984, 25, 51, 5831-5834 or Angewandte Chemie, 2005, 44, 9, 1378-1382. [ka]

[0069] As shown in Scheme 3, the compound of Formula 4 (wherein R' is a lower alkyl) can be prepared from the β-amino alcohol of Formula 5 by treatment with a carbonylating agent such as N,N'-carbonyldiimidazole (CDI), triphosgene, or dialkyl carbonate, typically in the presence of a base and a suitable co-solvent. Suitable organic bases for this reaction include, but are not limited to, piperidine, morpholine, triethylamine, 4-methylmorpholine, or N,N-diisopropylethylamine. This conversion can be carried out without a solvent or in a solvent such as tetrahydrofuran, toluene, or dichloromethane. Typically, this reaction is carried out in the range of 0°C to 80°C. For detailed procedures, see Tetrahedron, 2020, 76, 47, 131553 and its references. [ka]

[0070] As shown in Scheme 4, the β-amino alcohol (i.e., the compound of formula 5 where Y is O), which is the compound of formula 5a, can be synthesized by ring-opening the epoxide of formula 6 with a suitable aniline. Regioselective ring-opening can be achieved by simply refluxing the epoxide of formula 6 with aniline in a suitable solvent such as ethanol, or by treating it in anhydrous dichloromethane at room temperature in the presence of indium halide (InCl3 or InBr3). The epoxide of formula 6 is commercially available or can be prepared according to the method described in the literature procedure of U.S. Patent Application Publication No. 20040044249 or International Publication No. 2020102816. Aniline can be purchased commercially. Conditions under which the ring-opening reaction of the epoxide is promoted by indium halide are described in New Journal of Chemistry, 2001, 25(2), 221-222; Tetrahedron Letters, 2004, 45, 7495-7498. [ka]

[0071] As shown in Scheme 4A, the compound of formula 5b (i.e., the compound of formula 5 where Y is NH) can be synthesized by reducing the nitro compound of formula 7. Suitable reducing agents include, but are not limited to, zinc in acetate or Raney nickel in ethanol. The conditions for this reaction are described in Chemistry—An Asian Journal, 2013, 8(5), 877-882; Organic & Biomolecular Chemistry, 2005, 3(8), 1362-1364. [ka]

[0072] As shown in Scheme 4B, the nitro compounds of Formula 7 can be prepared from the corresponding nitroacetic acid esters of Formula 9 and the carbonyl compounds of Formula 8 by an aminomethylation reaction. The conditions for this type of reaction are described in Chemitsry—An Asian Journal, 2013, 8(5), 877-882. [ka]

[0073] As shown in Scheme 5, the amines of Formula 3 can be prepared by reacting the acid of Formula 7 with the amine, alcohol, or thiol of Formula 8 in the presence of a dehydration coupling reagent such as oxalyl chloride, thionyl chloride, propylphosphonic anhydride, dicyclohexylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), benzotriazole-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP), N,N'-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, or 2-chloro-1-methylpyridinium iodide. These reactions are typically carried out at temperatures of 0–60°C in solvents such as dichloromethane, acetonitrile, N,N-dimethylformamide, or ethyl acetate, in the presence of bases such as triethylamine, N,N-diisopropylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene. Specific synthetic examples are described in the Journal of Peptide Science, 2008, 14(2), 241–249. The amine of formula 3 (wherein X is O) is commercially available or can be prepared from a commercially available vinlactam by alkylation as described in Org. Process Res. Dev. 2018, 22, 337-343, International Publication No. 2017133667, Org. Lett. 2017, 19, 7, 1602-1605, or from a commercially available alcohol by using thionyl chloride as described in Tetrahedron Lett. 2001, 42, 1347-1350. Amines containing a tetrahydrofuran ring can be prepared by the method described in International Publication No. 2021170464. Amines containing cyclobutane can be purchased from commercially available suppliers. Amines containing bicyclic substitutions may be prepared by the procedures described in International Publication No. 2017133669 or Tetrahedron, 2010, 66, 3599-3607.Next, the N-Boc protecting group can be removed by acid treatment to obtain the desired chiral amine of formula 3 in the corresponding salt form. Examples of acids used in this reaction include trifluoroacetic acid or any other inorganic acid. [ka]

[0074] Those skilled in the art recognize that various functional groups can be converted to other functional groups in order to obtain different compounds of formula 1. For a valuable resource illustrating the interconversion of functional groups in a simple and direct manner, see Larock, RC, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2 nd See Ed., Wiley-VCH, New York, 1999.

[0075] For example, the intermediate for preparing the compound of formula 1 may contain an aromatic nitro group, which can be reduced to an amino group, which is then converted to various halides by reactions well known in the art, such as the Sandmeyer reaction, to obtain the compound of formula 1. The above reactions can often be carried out in a different order.

[0076] For example, R n A derivative of formula 1, in which is a halogen, particularly iodine or bromine, is reacted with an alkene, acetylene, phenyl, or 5- or 6-membered heteroaryl with a transition metal catalyst, such as a palladium(O) or palladium(II) catalyst, in a suitable solvent in the presence of a suitable base at a temperature of 20°C to 150°C, thereby R n A compound of formula 1 can be obtained in which is a substituted or unsubstituted alkene, alkyne, phenyl, 5- or 6-membered heteroaryl, etc. n The compound of formula 1, where is CN, can be hydrolyzed under acidic or basic conditions to yield a carboxylic acid, which can then be converted to an acid chloride, and subsequently to an amide by simple organic conversion.n Derivatives of formula 1 in which are halogens can also be converted to the corresponding alkoxyalkyl, aminoalkyl, or diaminoalkyl substituted compounds by treating them with a suitable alcohol or amine in a suitable solvent in the presence of a suitable base at a temperature of 0°C to 150°C.

[0077] It is recognized that some of the reagents and reaction conditions described above for preparing the compound of Formula 1 may not be compatible with certain functional groups present in the intermediate. In such cases, incorporating a series of protection / deprotection or functional group interconversions into the synthesis facilitates obtaining the desired product. The use and selection of protecting groups will be obvious to those skilled in chemical synthesis (see, for example, Greene, TW; Wuts, PGMProtective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, New Jersey, 1991). Those skilled in the art will recognize that, in some cases, after introducing a given reagent as shown in any of the individual schemes, it may be necessary to perform additional, standardized synthetic steps not detailed above to complete the synthesis of the compound of Formula 1. Those skilled in the art will also recognize that, in order to prepare the compound of Formula 1, it may be necessary to perform the combination of steps shown in the above schemes in an order other than that suggested by the particular scheme presented.

[0078] Those skilled in the art will also recognize that the compounds and intermediates of Formula 1 described herein can be subjected to a variety of electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0079] Without further detail, those skilled in the art will be able to make the most of the present invention using the foregoing description. Accordingly, the following examples should be construed as merely illustrative and not limiting the present disclosure. The steps in the following examples illustrate the procedure for each step of the overall synthetic transformation, and the starting materials in each step are not necessarily prepared by specific preparation operations described in other examples or steps. Percentages are by weight, except for the chromatographic solvent mixture or unless otherwise indicated. Parts and percentages for the chromatographic solvent mixture are by volume, unless otherwise indicated. All NMR spectra are reported in ppm on the low-field side of tetramethylsilane in CDCl3, measured at 500 MHz, unless otherwise specified, where s means singleline, brs means broad singleline, d means doubleline, t means tripleline, q means quadrupleline, p means quintupline, and m means multiline. [Examples]

[0080] Synthesis Example 1 Preparation of (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate methyl (compound 27) Step A: 3-(3,5-difluoroanilino)-2-hydroxy-2-methylpropanoate methyl To a solution of commercially available methyl 2-methyloxirane-2-carboxylate (1 g, 8.612 mmol, 1 equivalent) in dichloromethane (20 mL), 3,5-difluoroaniline (1.112 g, 8.612 mmol, 1 equivalent) was added at room temperature, and the reaction mixture was stirred for 10 minutes. Indium chloride (InCl3) (0.952 g, 4.306 mmol, 0.5 equivalents) was added to the reaction mixture in small amounts. After the addition was complete, the reaction mixture was stirred at room temperature for 14 hours. After the reaction was complete, the reaction mixture was stopped with ice water, extracted with dichloromethane (2 × 100 mL), and the organic layer was washed with water and saturated brine. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by elution with ethyl acetate / petroleum ether (0-15%) using silica gel column chromatography, and the desired methyl 3-(3,5-difluoroanilino)-2-hydroxy-2-methyl-propanoate (1.2 g, yield 50%) was isolated as an off-white solid. 1 H NMR δ 1.46(s,3H),3.19-3.22(dd,1H),3.45(s,1H),3.49-3.53(dd,1H)3.77(s,3H)4.24(bs,1H),6.09-6.17(m,3H).

[0081] Step B: Synthesis of methyl 3-(3,5-difluorophenyl)-5-methyl-2-oxo-oxazolidine-5-carboxylate To a 20 mL solution of methyl 3-(3,5-difluoroanilino)-2-hydroxy-2-methylpropanoate (i.e., the product of step A) (1.5 g, 6.117 mmol, 1 equivalent) in dichloromethane, triethylamine (0.853 mL, 6.117 mmol, 1 equivalent) and triphosgene (1.815 g, 6.117 mmol, 1 equivalent) in dichloromethane (5 mL) were added dropwise at 0°C. After the additions were complete, the reaction mixture was slowly warmed to room temperature and stirred for a further 14 hours. After the reaction was complete, the reaction mixture was stopped with ice water and extracted with dichloromethane (2 × 100 mL). The organic layers were combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The crude product was purified by elution with ethyl acetate / petroleum ether (0-30%) using silica gel column chromatography, and the desired methyl 3-(3,5-difluorophenyl)-5-methyl-2-oxo-oxazolidine-5-carboxylate (1.01 g, yield 91%) was isolated as a white solid. 1 H NMR δ ppm 1.79(s,3H),3.80-3.82(d,1H),3.86(s,3H),4.29-4.31(d,1H),6.59-6.63(m,1H),7.11-7.16(m,2H).

[0082] Step C: Preparation of 3-(3,5-difluorophenyl)-5-methyl-2-oxo-oxazolidine-5-carboxylic acid To a solution of methyl 3-(3,5-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-5-carboxylic acid (i.e., the product of step B) (1 g, 3.687 mmol, 1 equivalent) in tetrahydrofuran (10 mL), potassium trimethylsilanolate (473 mg, 3.687 mmol, 1 equivalent) was added at 0°C, and the reaction was stirred for 1 hour. The solution was stopped with 2N HCl, and extracted with ethyl acetate (2 × 100 mL). The organic layers were combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The crude 3-(3,5-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-5-carboxylic acid (650 mg, 68.5% yield) was of sufficient purity for use in the next step. 1 H NMR(500MHz,DMSO-d6)δ 1.64(m,3H),3.99-4.02(d,2H),4.28-4.30(d,1H),6.96-6.99(m,1H),7.30-7.33(m,2H),13.78(bs,1H).

[0083] Step D: Preparation of (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate methyl 3-(3,5-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-5-carboxylic acid (i.e., the product of step C) (5 g, 19.441 mmol, 1 equivalent) and (1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid methyl hydrochloride (4.144 g, 23.329 mmol, 1.2 equivalents), prepared according to the procedure described in International Publication No. 2017133667, were dissolved in dichloromethane (100 mL). While stirring the solution, N,N-diisopropylethylamine (6.791 mL, 38.881 mmol, 2 equivalents) and PyBOP (20.234 g, 38.881 mmol, 2 equivalents) were added at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After the reaction was complete, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (2 × 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude residue. The crude product was purified by elution with ethyl acetate / petroleum ether (0-50%) using silica gel column chromatography to obtain (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate methyl (6 g, yield 81.1%) as a diastereomer mixture. 1H NMR δppm 1.74-1.76(s,3H),1.93-1.99(m,1H),2.44-2.54(m,1H),3.53-3.56(m,1H),3.75(m,3H),3.80-3.81( m,1H),4.33-4.35(m,1H),5.01-5.05(m,1H),5.85-6.00(m,2H),6.59-6.63(m,1H),7.08-7.16(m,3H).

[0084] Synthesis Example 2 Preparation of (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid (compound 51) Step A: Preparation of (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid (1S,4R)-4-[3-(3,5-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-5-amide]cyclopent-2-ene-1-carboxylate methyl (i.e., the product of Synthesis Example 1) (6 g, 15.775 mmol, 1 equivalent) obtained in step A was dissolved in acetonitrile / water (150 mL, 4:1) solution. Triethylamine (10.994 mL, 78.875 mmol, 5 equivalents) and lithium bromide (13.7 g, 157.75 mmol, 10 equivalents) were added to the solution while stirring at room temperature. The reaction mixture was stirred at room temperature for 72 hours. After the reaction was complete, the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (30 mL). The aqueous organic layer was acidified with 1 N HCl solution and extracted with ethyl acetate (3 × 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude residue. The crude product was purified by elution with methanol / dichloromethane (0-10%) using silica gel column chromatography, and then recrystallized using dichloromethane and hexane to obtain (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid (3.01 g, yield 50%, diastereomer mixture) as a white solid. 1 H NMR(500MHz,DMSO-d6)δ 1.62(s,3H),1.84-1.91(m,1H),2.37-2.44(m,1H),3.45-3.64(m,1H),3.95-3.98(d,1H),4.21-4.27(m,1H),4.78-4.93 (m,1H),5.74-5.79(m,1H),5.89-5.92(m,1H),7.00-7.05(m,1H),7.34-7.36(m,2H),8.30-8.34(t,3H),12.41(bs,1H).

[0085] Synthesis Example 3 Preparation of (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl (compound 48) Step A: Preparation of (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl (1S,4R)-4-[3-(3,5-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-5-amide]cyclopent-2-ene-1-carboxylic acid (i.e., the product of Synthesis Example 2) (250 mg, 0.682 mmol, 1 equivalent) and 2-(methylthio)ethanol (0.094 g, 1.024 mmol, 1.5 equivalents) were mixed in a 6 mL solution of dichloromethane while stirring. PyBOP (0.71 g, 1.365 mmol, 2 equivalents) and N,N-diisopropylethylamine (0.362 mL, 2.047 mmol, 3 equivalents) were added at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After the reaction was complete, the reaction mixture was concentrated under reduced pressure to obtain the crude residue. The crude product was purified by elution with ethyl acetate / petroleum ether (0%~50%) using silica gel column chromatography to obtain (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl (210 mg, yield 69.9%, diastereomer mixture). 1 H NMR δ 1.74-176(m,3H),1.91-2.02(m,1H),2.15-2.18(m,4H),2.42-2.55(m,1H),2.70-2.81(m,3H),3.54-3.59(m,1H), 3.75-3.82(m,2H),4.25-4.38(m,4H),5.03-5.15(m,1H),5.62-6.04(m,2H),6.57-6.65(m,1H),7.05-7.17(m,3H).

[0086] Synthesis Example 4 Preparation of (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl (compound 37) While stirring a solution of 3-(3,5-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-5-carboxylic acid (i.e., the product of step C of Synthesis Example 1) (350 mg, 1.361 mmol, 1 equivalent) in dichloromethane (9 mL), the following were added at room temperature: triflate salt of (4S)-4-amino-1-cyclopentene-1-carboxylate (0.521 g, 2.041 mmol, 1.5 equivalents), PyBOP (1.416 g, 2.722 mmol, 2 equivalents), and N,N-diisopropylethylamine (0.528 g, 4.083 mmol, 3 equivalents), prepared according to the procedure described in Org. Lett. 2017, 19, 7, 1602-1605. The reaction mixture was stirred at room temperature for 16 hours. After the reaction was complete, the reaction mixture was concentrated under reduced pressure to obtain the crude residue. The crude product was purified by elution with ethyl acetate / petroleum ether (0%~60%) using silica gel column chromatography to obtain (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl (350 mg, 0.92 mmol, yield 67.6%, diastereomer mixture) as a white solid. 1 H NMR δ 1.73-1.74(s,3H),2.37-2.54(m,2H),2.92-3.10(m,2H),3.75-3.77(s,3H),3.79-3.81(dd,1H), 4.31-4.34(dd,1H),4.58-4.67(m,1H),6.58-6.66(m,1H),6.71-6.82(m,2H),7.09-7.16(m,2H).

[0087] Synthesis Example 5 Preparation of (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid (compound 38) (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl (i.e., the product of Synthesis Example 4) (1.6 g, 4.207 mmol, 1 equivalent) was added in acetonitrile / water (20 mL, 4:1) mixture while stirring at 0°C, with lithium bromide (4.384 g, 50.48 mmol, 12 equivalents) added in small amounts, followed by triethylamine (0.851 g, 8.413 mmol, 2 equivalents), and the mixture was stirred at room temperature for 72 hours. After the reaction was complete, the reaction mixture was diluted with water and extracted with ethyl acetate (2 × 100 mL). The aqueous layer was acidified with 1 M HCl solution and extracted with ethyl acetate (2 × 100 mL). The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure to obtain (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid (550 mg, 1.501 mmol, yield 35.7%, mixture of diastereomers) as an off-white solid. 1 H NMR δ 1.75-1.76(s,3H),2.44-2.54(m,1H),2.55-2.66(m,1H),2.96-3.09(m,3H),3.81-3.83(d,1H), 4.34-4.36(d,1H),4.58-4.68(m,1H),6.58-6.66(m,1H),6.80-6.87(m,1H),7.08-7.19(m,2H).

[0088] Synthesis Example 6 Preparation of (1R,2S,4R,5S)-4-[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-oxazolidine-5-carbonyl]amino]bicyclo[3.1.0]methyl hexane-2-carboxylate:(compound number 176) 3-(3,5-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-5-carboxylic acid (i.e., the product of step C of Synthesis Example 1, 300 mg, 0.11 mmol, 1 equivalent), a solution of (1R,2S,4R,5S)-4-aminobicyclo[3.1.0]hexane-2-carboxylate methyl (271 mg, 0.17 mmol, 1.5 equivalents) prepared according to the procedure described in International Publication No. 2017133669 in dichloromethane (5 mL), was stirred along with N,N-diisopropylethylamine (0.6 mL, 0.35 mmol, 3 equivalents), and PyBOP® ((benzotriazole-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (88 mg, 0.17 mL)). (mol, 1.5 equivalents) were added at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After the reaction was complete, the reaction mixture was diluted with water (20 mL) and extracted with dichloromethane (2 × 20 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude residue. The crude product was purified by elution with ethyl acetate / petroleum ether (0-50%) by silica gel column chromatography to obtain (1R,2S,4R,5S)-4-[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-oxazolidine-5-carbonyl]amino]bicyclo[3.1.0]hexane-2-carboxylate methyl (0.2 g, yield 43%) as a diastereomer mixture. 1 H NMR(400MHz,DMSO-d6):δ 0.30-0.33(m,1H),0.80-0.81(m,1H),1.51-1.59(m,6H),1.80-1.85(m,1H),3.03-3.04(m,1H),3.61(S,3H),3 .94-3.97(m,1H),4.18-4.26(m,1H),4.41-4.42(m,1H),7.01(t,1H),7.32-7.38(m,2H),8.20(t,1H).MS[M+H] + :395.23

[0089] Synthesis Example 7 Preparation of 3-[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-oxazolidine-5-carbonyl]amino]cyclobutanecarboxylate methyl (compound 118) While stirring a solution of 3-(3,5-difluorophenyl)-5-methyl-2-oxo-1,3-oxazolidine-5-carboxylic acid (i.e., the product of step C of Synthesis Example 1) (1.2 g, 4.66 mmol, 1 equivalent) and (1S,3S)-3-aminocyclobutane-1-carboxylate methyl (0.904 g, 6.999 mmol, 1.5 equivalents) in dichloromethane (24 mL), N,N-diisopropylethylamine (1.206 g, 9.332 mmol, 2 equivalents) and PyBOP® ((benzotriazole-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) (4.856 g, 9.332 mmol, 2 equivalents) in dichloromethane (24 mL), N,N-diisopropylethylamine (1.206 g, 9.332 mmol, 2 equivalents) is added. Each component was added at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After the reaction was complete, the reaction mixture was diluted with water (50 mL) and extracted with dichloromethane (2 × 50 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude residue. The crude product was purified by elution with ethyl acetate / petroleum ether (0-50%) using silica gel column chromatography to obtain 3-[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-oxazolidine-5-carbonyl]amino]cyclobutanecarboxylate methyl (1.25 g, yield 69.1%) as a diastereomer mixture. 1 H NMR(500MHz,CDCl3):δ 1.73(S,3H),2.20-2.26(m,2H),2.60-2.70(m,2H),2.82-2.89(m,1H),3.70(s,3H),3.78-3.80(d,1H),4 .31-4.33(d,1H),4.37-4.40(m,1H),6.59-6.63(m,1H),6.92-6.94(bd,1H),7.10-7.16(m,2H).MS[M+H] + -369.3 (ES+)

[0090] Synthesis Example 8 Preparation of (1S,4R)-4-[[1-(3,5-difluorophenyl)-4-methyl-2-oxoimidazolidined-4-carbonyl]amino]cyclopent-2-ene-1-carboxylate methyl [ka] Step A: Preparation of ethyl 3-(3,5-difluoroanilino)-2-methyl-2-nitropropanoate A methanol (10 mL) solution of ethyl 2-nitropropanoate (1 g, 6.8 mmol) was stirred, and compound 3,5-difluoroaniline (0.877 g, 6.802 mmol) and an aqueous solution of 37% formalin (0.66 g, 8.163 mmol) were added at 25°C. The reaction mixture was stirred at 80°C for 3 hours. Thin-layer chromatography analysis indicated that the reaction was complete. The reaction mixture was concentrated under reduced pressure to obtain the crude product, which was then placed on a silica gel column. Elution from the column with 5% ethyl acetate in petroleum ether yielded ethyl 3-(3,5-difluoroanilino)-2-methyl-2-nitropropanoate as a colorless liquid (0.7 g, yield 36.8%). 1 H NMR(400MHz,d6-DMSO)δ 6.48(t,1H),6.39(dd,2H),6.28(td,1H),4.20(q,2H),4.04(dd,1H),3.87(dd,1H),1.78(s,3H),1.19(t,3H).MS(CI)m / e=289(M+1).

[0091] Step B: Preparation of ethyl 2-amino-3-(3,5-difluoroanilino)-2-methylpropanoate Raney nickel (0.457 g, 7.812 mmol) was added to a solution of ethyl 3-(3,5-difluoroanilino)-2-methyl-2-nitropropanoate (1.5 g, 5.2 mmol) in ethanol (30 mL). The reaction mixture was stirred at 25°C for 12 hours in a hydrogen atmosphere of 50 psi (approximately 2.07 e+005 Newtons / m²). Thin-layer chromatography analysis indicated that the reaction was complete. The reaction mixture was filtered through a Celite® (diatomaceous earth filter aid) pad, and the crude product was obtained by evaporating the filtrate under reduced pressure, which was then placed on a silica gel column. Elution from the column with 20% ethyl acetate in petroleum ether yielded ethyl 2-amino-3-(3,5-difluoroanilino)-2-methylpropanoate as an off-white solid (0.9 g, 67% yield). 1 H NMR(400MHz,d6-DMSO)δ 6.28(dd,2H),6.21-6.15(m,2H),4.05-3.95(m,2H),3.30(m,1H),3.08(dd,1H),2.04(br s,2H),1.23(s,3H),1,13(t,3H).MS(CI)m / e=259(M+1).

[0092] Step C: Preparation of ethyl 1-(3,5-difluorophenyl)-4-methyl-2-oxoimidazolidined-4-carboxylate A solution of ethyl 2-amino-3-(3,5-difluoroanilino)-2-methyl-propanoate (i.e., the product of step B, 3.1 g, 12.02 mmol) in dichloromethane (30 mL) was stirred while adding triethylamine (1.8 g, 18.02 mmol) and triphosgene (3.55 g, 12.02 mmol) at 0°C. The resulting mixture was stirred at 25°C for 12 hours. Thin-layer chromatography analysis indicated that the reaction was complete. The mixture was diluted with cold water (20 mL), extracted with dichloromethane (2 × 50 mL), and the organic layer was dried over anhydrous sodium sulfate. The crude product was concentrated under reduced pressure to obtain the crude product. Purification by elution with 15% ethyl acetate in petroleum ether using a silica gel column yielded pure ethyl 1-(3,5-difluorophenyl)-4-methyl-2-oxo-imidazolidined-4-carboxylate as an off-white solid (2.3 g, yield 67%). 1 H NMR(400MHz,d6-DMSO)δ 8.06(s,1H),7.30(dd,2H),6.82(td,1H),4.18(q,2H),4.12(d,1H),3.75(d,1H),1.48(s,3H),1.21(t,3H).MS(CI)m / e=285(M+1).

[0093] Step D: Preparation of 1-(3,5-difluorophenyl)-4-methyl-2-oxoimidazolidined-4-carboxylic acid Ethyl 1-(3,5-difluorophenyl)-4-methyl-2-oxo-imidazolidined-4-carboxylic acid (i.e., the product of step C, 0.3 g, 1.06 mmol) was added to a solution of methanol (9 mL) and water (3 mL) with stirring, while LiOH·H2O (88 mg, 2.112 mmol) was added at 25°C. The reaction mixture was stirred at 80°C for 2 hours. Thin-layer chromatography analysis indicated that the reaction was complete. The reaction mixture was concentrated under reduced pressure and then diluted with water (20 mL). Acidification of the pH to approximately 4 with citric acid formed a solid, which was filtered and vacuum-dried to obtain 1-(3,5-difluorophenyl)-4-methyl-2-oxo-imidazolidined-4-carboxylic acid as an off-white solid (0.210 g, yield 77%). 1 H NMR(400MHz,d6-DMSO)δ 13.24(br s,1H),7.97(s,1H),7.30(dt,2H),6.80(tt,1H),4.09(d,1H),3.70(d,1H),1.46(s,3H).MS(CI)m / e=257(M+1).

[0094] Step E: Preparation of (1S,4R)-4-[[1-(3,5-difluorophenyl)-4-methyl-2-oxoimidazolidin-4-carbonyl]amino]cyclopent-2-ene-1-carboxylate methyl To a solution of 1-(3,5-difluorophenyl)-4-methyl-2-oxo-imidazolidined-4-carboxylic acid (i.e., the product of step D, 240 mg, 0.936 mmol) and (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate methyl (244 mg, 1.72 mmol) in dichloromethane (10 mL), N,N-diisopropylethylamine (0.67 mL, 3.86 mmol) and PyBOP® ((benzotriazole-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, 0.761 g, 1.46 mmol) were added at 0°C. The reaction mixture was stirred at 25°C for 16 hours. Thin-layer chromatography analysis indicated that the reaction was complete. The resulting mixture was diluted with cold water (50 mL), extracted with ethyl acetate (2 × 50 mL) to combine the organic layers, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the crude product. By chromatography using silica gel and elution with 15% ethyl acetate in petroleum ether, (1S,4R)-4-[[1-(3,5-difluorophenyl)-4-methyl-2-oxo-imidazolidin-4-carbonyl]amino]cyclopent-2-ene-1-carboxylate methyl as an off-white solid (186 mg, yield 52%). 1 H NMR(400MHz,d6-DMSO)δ 7.92(t,1H),7.69(s,1H),7.30(dt,2H),6.81(tt,1H),5.92-5.88(m,1H),5.82-5.77(m,1H),4.81(br s,1H),4.00(dd,1H),3.70(d,1H),3.64(d,3H),3.60-3.53(m,1H),1.85-1.75(m,1H),1.43(s,3H).MS(CI)m / e=380(M+1).

[0095] The compounds listed in Tables 1-200 below can be prepared by using the procedures described herein in conjunction with methods known in the art. The following abbreviations are used in the tables below: t means tertiary, s means secondary, n means normal, i means iso, c means cyclic, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, i-Pr means isopropyl, c-Pr means cyclopropyl, t-Bu means tertiary butyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, -CN means cyano, -NO2 means nitro, TMS means trimethylsilyl, SOMe means methylsulfinyl, C2F5 means CF2CF3, SO2Me means methylsulfonyl, and the number before the "-" following an atom indicates the position of the atom, e.g., (R) n If it is 3-F, the substituent F is at the 3-position of the phenyl ring.

[0096] [Table 5]

[0097] [Table 6]

[0098] [Table 7]

[0099] [Table 8]

[0100] [Table 9]

[0101] [Table 10]

[0102] This disclosure also includes Tables 2-100, each of which is a reference to the table heading of Table 1 (i.e., R 1 =R 2 =R 4 =H, R 3 It has the same configuration as Table 1 above, except that =CH3 and Z=Z-1) are replaced with the table headings shown below.

[0103] [Table 11]

[0104] [Table 12]

[0105] [Table 13]

[0106] [Table 14]

[0107] [Table 15]

[0108] [Table 16]

[0109] [Table 17]

[0110] [Table 18]

[0111] This disclosure also includes Tables 102-200, each of which is a reference to the table heading of Table 101 (i.e., R 1 =R 2 =R 4 =H, R 3 It has the same configuration as Table 101 above, except that =CH3 and Z=Z-1) are replaced with the table headings shown below.

[0112] [Table 19]

[0113] [Table 20]

[0114] [Table 21]

[0115] Table 201 Table 201 has the same configuration as Table 1, except that the structure has been replaced with the following structure: [ka] (In the formula, R 1 , R 2 , R 3 , R 4 (And Z are equivalent to those in Table 1, and the remaining variable elements are equivalent to those in Table 1).

[0116] This disclosure also includes Tables 202-300, each of which is a reference to the table headings in Table 1 (i.e., R 1 =R 2 =R 4 =H, R 3 It has the same configuration as Table 201 above, except that =CH3 and Z=Z-1) are replaced with the table headings shown in Tables 2 to 100 above.

[0117] Table 301 Table 301 has the same configuration as Table 101, except that the structure has been replaced with the following structure: [ka] (In the formula, R 1 , R 2 , R 3 , R 4 (And Z are equivalent to those in Table 1, and the remaining variable elements are equivalent to those in Table 101).

[0118] This disclosure also includes Tables 302-400, each of which is a reference to the table heading of Table 301 (i.e., R 1 =R 2 =R 4 =H, R 3 It has the same configuration as Table 301 above, except that =CH3 and Z=Z-1) are replaced with the table headings shown in Tables 101 to 200 above.

[0119] Formulation / Practicality The compounds of the present invention will generally be used as herbicidal active ingredients in a composition, i.e., a formulation, together with at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents, which will function as a carrier. The components of the formulation or composition will be selected to be compatible with the physical properties of the active ingredient, the method of application, and environmental factors such as soil type, humidity, and temperature.

[0120] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifying concentrates), suspensions, and emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates, and / or suspendemulsions), which can be optionally thickened to form gels. Common types of aqueous liquid compositions include soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, flowable concentrates, and suspendemulsions. Common types of non-aqueous liquid compositions include emulsifying concentrates, microemulsifying concentrates, dispersible concentrates, and oil dispersants.

[0121] Common types of solid compositions include powders, granules, pellets, granules, solid fumigants, tablets, and active ingredient-containing films (including seed coatings), which may be water-dispersible ("wet") or water-soluble. Films and coatings formed from film-forming solutions or fluid suspensions are particularly useful for seed treatment. Active ingredients may be (micro)encapsulated and further formed into suspension formulations or solid formulations, or the entire active ingredient formulation may be encapsulated (or "overcoated"). Encapsulation can control or delay the release of the active ingredient. Emulsified granules combine the advantages of both emulsified concentrate formulations and dry granular formulations. High-concentration compositions are primarily used as intermediates for further formulation.

[0122] Sprayable formulations are typically diluted with a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily dilutable in the spray medium, which is usually water, but may also be other suitable mediums such as aromatic or paraffinic hydrocarbons or vegetable oils. Spray volumes can range from approximately 1 to several thousand liters per hectare, but more typically from approximately 10 to several hundred liters per hectare. When sprayable formulations are applied to foliar areas by aerial or ground application, or to plant growth media, they can be tank-mixed with water or other suitable mediums. Liquid and dry formulations can be directly metered and supplied to drip irrigation systems or metered and supplied to planting furrows at planting time.

[0123] The formulation will typically contain an effective amount of the active ingredient, a diluent, and a surfactant, totaling 100 percent by weight, within the approximate range shown below.

[0124] [Table 22]

[0125] Examples of solid diluents include clays such as bentonite, montmorillonite, attapulgite, and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate, sodium bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.

[0126] Examples of liquid diluents include water, N,N-dimethylalkaneamide (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidone (e.g., N-methylpyrrolidinone), alkyl phosphate (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffin (e.g., liquid paraffin, normal paraffin, isoparaffin), alkylbenzene, alkylnaphthalene, glycerin, glyceryl triacetate, sorbitol, aromatic hydrocarbons, de-aromaticated aliphatic compounds, alkylbenzene, alkylnaphthalene, ketones, such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-pentano Examples of liquid diluents include acetate esters, such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters, such as alkylated lactic acid esters, dibasic esters, alkyl and aryl benzoates, and γ-butyrolactone, as well as alcohols that may be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Examples of liquid diluents include saturated and unsaturated fatty acids (typically C6-C6). 22Examples of liquid diluents include glycerol esters of plant and animal glycerol esters, such as plant seed oils and fruit oils (e.g., olive oil, castor oil, linseed oil, sesame oil, corn oil, peanut oil, sunflower oil, grape seed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, coconut oil, palm kernel oil), animal fats (e.g., beef tallow, lard, cod liver oil, fish oil), and mixtures thereof. Alkylated fatty acids (e.g., methylated, ethylated, butylated) can also be used as liquid diluents, and these fatty acids can be obtained by hydrolysis of plant and animal glycerol esters and purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[0127] The solid and liquid compositions of the present invention often contain one or more surfactants. When added to a liquid, surfactants (also known as "surfactants") generally alter, and in most cases reduce, the surface tension of the liquid. Depending on the hydrophilic and lipophilic properties of the surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers, or defoamers.

[0128] Surfactants can be classified as nonionic, anionic, or cationic. Nonionic surfactants useful in this composition include, but are not limited to, alcohol alkoxylates, e.g., alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) prepared from this alcohol with ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides, e.g., ethoxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxylates, e.g., octylphenol ethoxylate, nonylphenol ethoxylate, dinonylphenol ethoxylate, and dodecylphenol ethoxylate (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide; and reversed-phase polymers where the terminal blocks are prepared from propylene oxide. Examples include block polymers, ethoxylated fatty acids, ethoxylated fatty acid esters and oils, ethoxylated methyl esters, ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof), fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters, such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters, and polyethoxylated glycerol fatty acid esters, other sorbitan derivatives, such as sorbitan esters, polymeric surfactants, such as random copolymers, block copolymers, alkyd PEG (polyethylene glycol) resins, graft or comb-type polymers and star-type polymers, polyethylene glycol (PEG), polyethylene glycol fatty acid esters, silicone-based surfactants, and sugar derivatives, such as sucrose esters, alkyl polyglycosides, and alkyl polysaccharides.

[0129] Useful anionic surfactants include, but are not limited to, alkylaryl sulfonic acids and their salts, carboxylated alcohols or alkylphenol ethoxylates, diphenyl sulfonate derivatives, lignin and lignin derivatives, such as lignosulfonates, maleic acid or succinic acid or their anhydrides, olefin sulfonates, phosphate esters, such as alcohol alkoxylate phosphate esters, alkylphenol alkoxylate phosphate esters and styrylphenol ethoxylate phosphate esters, protein-based surfactants, sarcosine derivatives, and styrylphenol Examples include ether sulfates, sulfates and sulfonates of oils and fatty acids, sulfates and sulfonates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, sulfonates of amines and amides, such as sulfonates of N,N-alkyltaurine, benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzene, sulfonates of condensed naphthalene, sulfonates of naphthalene and alkylnaphthalene, sulfonates of petroleum distillates, sulfosuccinates and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinates.

[0130] Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides, amines such as N-alkylpropanediamine, trippropyltriamine and dipropylenetetramine and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butylene 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 alkyldimethylamine oxide and bis(2-hydroxyethyl)alkylamine oxide.

[0131] Mixtures of nonionic and anionic surfactants, or mixtures of nonionic and cationic surfactants, are also useful in this composition. Nonionic, anionic, and cationic surfactants and their recommended uses are disclosed in various publicly available references, including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[0132] The compositions of the present invention may also include formulation aids and additives known to those skilled in the art as formulation aids (some of which can be considered to function as solid diluents, liquid diluents, or surfactants). Such formulation aids and additives can control pH (buffering agents), foaming during processing (antifoaming agents such as polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), growth of microorganisms in the container (antimicrobial agents), freezing of the product (antifreeze agents), color (dye / pigment dispersions), washability (film-forming agents or adhesives), evaporation (evaporation retarders), and other formulation attributes. Examples of film-forming agents include polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation aids and additives are listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions, published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co., and in the PCT publication, International Publication No. 03 / 024222.

[0133] Compounds of Formula 1 and any other active ingredients are typically incorporated into the composition by dissolving the active ingredient in a solvent or by grinding it in a liquid or dry diluent. Solutions (including emulsifiable concentrates) can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is immiscible with water, an emulsifier is usually added to emulsify when diluting the solvent containing the active ingredient with water. Slurries of active ingredients with a particle diameter of 2,000 μm or less can be wet-ground using a medium-agitated mill to an average particle diameter of less than 3 μm. Aqueous slurries can be made into a finished suspension concentrate (see, for example, U.S. Patent No. 3,060,084) or further processed by spray-drying to form water-dispersible granules. Dry formulations typically require dry grinding to achieve an average particle diameter in the range of 2 to 10 μm. Powders and powders can be prepared by blending and usually by grinding (e.g., using a hammer mill or fluid energy mill). Granules and pellets can be prepared by spraying the active substance onto a pre-formed granular carrier or by using an agglomeration technique. See Browning, “Agglomeration”, Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and thereafter, and International Publication No. 91 / 13546. Pellets can be prepared as described in U.S. Patent No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442, and German Patent No. 3,246,493. The tablets may be prepared as taught in U.S. Patent No. 5,180,587, U.S. Patent No. 5,232,701, and U.S. Patent No. 5,208,030. The coatings may be prepared as taught in British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

[0134] For further information on formulation technology, see T.Swoods, “The Formulator's Toolbox—Product Forms for Modern Agriculture,” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and TR. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120–133. Similarly, U.S. Patent No. 3,235,361, column 6, line 16 to column 7, line 19 and Examples 10-41; U.S. Patent No. 3,309,192, column 5, line 43 to column 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Patent No. 2,891,855, column 3, line 66 to column 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Developments in formulation technology, PJB See also Publications, Richmond, UK, 2000.

[0135] In the following examples, all percentages are by weight, and all formulations are prepared by conventional methods. Compound numbers refer to compounds in Index Table A. Without further detail, those skilled in the art will be able to make the most of the present invention using the foregoing description. Therefore, the following examples should be construed as merely illustrative and not limiting the present disclosure. Unless otherwise specified, percentages are by weight.

[0136] Example A Highly concentrated concentrate Compound 1 98.5% Silica aerogel 0.5% Synthetic amorphous fine silica 1.0%

[0137] Example B Wettable powder Compound 1 65.0% Dodecylphenol polyethylene glycol ether 2.0% Sodium lignosulfonate 4.0% Sodium aluminosilicate 6.0% Montmorillonite (calcined) 23.0%

[0138] Example C Granules Compound 1 10.0% Granular attapulgite (low volatility, 0.71 / 0.30 mm, US Standard Sieve No. 25-50) 90.0%

[0139] Example D Extruded pellets Compound 1 25.0% Anhydrous sodium sulfate 10.0% Crude calcium lignin sulfonate 5.0% Sodium alkylnaphthalene sulfonate 1.0% Calcium / magnesium type bentonite 59.0%

[0140] Example E emulsifiable concentrate Compound 1 10.0% Polyoxyethylene sorbitol hexoleate 20.0% C6~C 10 Fatty acid methyl ester 70.0%

[0141] Example F Microemulsion Compound 1 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglycoside 30.0% Glyceryl monooleate 15.0% Water 20.0%

[0142] Example G Suspension concentrate Compound 1 35% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic acid copolymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Water 53.7%

[0143] Example H Underwater emulsion Compound 1 10.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic acid copolymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone-based defoaming agent 0.1% 1,2-Benzisothiazolin-3-one 0.1% Petroleum-based aromatic hydrocarbons 20.0 Water 58.7%

[0144] Example I Oil dispersant Compound 1 25% Polyoxyethylene sorbitol hexaoleate 15% Organically modified bentonite clay 2.5% Fatty acid methyl ester 57.5%

[0145] This disclosure also includes Examples A to I, in which "Compound 1" is replaced with any one of "Compound 2" to "Compound 204".

[0146] Test results indicate that the compounds of the present invention are highly active pre-emergence and / or post-emergence herbicides and / or plant growth regulators. The compounds of the present invention generally exhibit the highest activity in post-emergence weed control (i.e., application after weed seedlings emerge from the soil) and pre-emergence weed control (i.e., application before weed seedlings emerge from the soil). Many of these are useful for broad-spectrum pre-emergence and / or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, landing pads, riverbanks, irrigation canals and other waterways, around billboards, and highway and railway structures. Many of the compounds of the present invention are useful for selective control of grasses and broadleaf weeds in crop / weed mixtures by selective selection due to metabolic differences between crops and weeds, or selective selection due to differences in activity at physiological inhibition sites in crops and weeds, or by selective placement on or within the surface of environments where crops and weeds coexist. Those skilled in the art will recognize that preferred combinations of these selectivity factors in a compound or group of compounds can be easily determined by performing standard biological and / or biochemical tests. Key agricultural crops, including, but not limited to, alfalfa, barley, cotton, wheat, rapeseed, sugar beet, corn, sorghum, soybean, rice, oat, peanut, vegetables, tomato, potato, coffee, cocoa, oil palm, rubber, sugarcane, citrus fruits, grapes, fruit trees, nut trees, bananas, plantains, pineapples, hops, and tea, as well as forest trees such as eucalyptus and conifers (e.g., loblolly pine) and turfgrass species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue, and Bermuda grass), may exhibit resistance to the compounds of the present invention. The compounds of the present invention can be used in genetically transformed or bred crops for the purpose of incorporating herbicide resistance, expressing proteins toxic to invertebrate pests (e.g., Bacillus thuringiensis toxin), and / or expressing other useful traits.Those skilled in the art will understand that not all compounds exhibit equal effectiveness against all weeds. Instead, the compounds in question are useful for regulating plant growth.

[0147] The compounds of the present invention have herbicidal activity both before and after emergence, and control undesirable vegetation by killing or damaging vegetation or inhibiting its growth. Therefore, the compounds can be usefully applied by various methods, including contacting the leaf surface or other parts of the undesirable vegetation or the environment of the undesirable vegetation, such as soil or water surrounding the growth of the undesirable vegetation or the seeds or other reproductive bodies of the undesirable vegetation, with the soil or water surrounding the seeds or other reproductive bodies of the undesirable vegetation. Undesirable vegetation includes at least one selected from the group consisting of grasses and broadleaf weeds. Undesirable vegetation includes annual bluegrass, round-leaved dayflower, wild bellflower, black nightshade, European thorny thistle, black tea flea, cocklebur (Xanthium pensylvanicum), ragweed, poppy, meadowsweet, autumn foxtail grass, goosegrass, foxtail grass, guinea grass, beggar-ticks, herbicide-resistant wild bellflower, dwarf edelweiss, Italian ryegrass, datura, and halepia (Sorghum). The group is selected from the following: halepense, crabgrass, little seed canarygrass, morning glory, American knotweed, wild morning glory, American golden sedge, ryegrass, blue amaranth, shutter cane, shepherd's purse, silky windgrass, sunflower (as a potato weed), buckwheat vine (Polygonum convolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua), wild poinsettia, golden foxtail grass, and edible sedge (Cyperus esculentus).

[0148] The effective herbicidal amount of the compound of the present invention is determined by many factors. These factors include the selected formulation, application method, amount and type of vegetation present, and growth conditions. Generally, the effective herbicidal amount of the compound of the present invention is about 0.001 to 20 kg / ha, with a preferred range of about 0.004 to 1 kg / ha. Those skilled in the art can easily determine the effective herbicidal amount required for the desired level of weed control.

[0149] In a typical embodiment, the compounds of the present invention are typically applied in a formulated composition to a habitat containing desirable vegetation (e.g., crops) and undesirable vegetation (i.e., weeds) (both of which may be seeds, seedlings, and / or more mature plants) in contact with a growth medium (e.g., soil). In this habitat, the composition containing the compounds of the present invention may be applied directly to the plant bodies or parts thereof of the particularly undesirable vegetation and / or to the growth medium in contact with the plant bodies.

[0150] Most typically, the compounds of the present invention are used to control undesirable vegetation, but when desirable vegetation comes into contact with the compounds in the treated habitat, it may produce an additive or enhanced effect on the genetic traits of the desirable vegetation (including traits incorporated through genetic recombination). For example, resistance to herbivorous insect pests or plant diseases, tolerance to biot / abiotic stress, or storage stability may be higher than expected from the genetic traits of the desirable vegetation.

[0151] The compounds of the present invention can also be mixed with herbicides, herbicide phytotoxicity reducers, fungicides, insecticides, nematicides, bactericidal agents, acaricides, growth regulators such as insect molting inhibitors and rooting promoters, sterilizers, signaling chemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other bioactive compounds, or one or more other bioactive compounds or agents such as entomopathogenic bacteria, viruses or fungi to form multi-component pest control agents, further expanding the agricultural protection spectrum. Mixtures of the compounds of the present invention with other herbicides can expand the activity spectrum against further weed species and suppress the proliferation of resistant biotypes. Accordingly, the present invention also relates to compositions comprising the compound of Formula 1 (in a herbicidal effective amount) and at least one additional bioactive compound or agent (in a bioactive amount), which may further comprise at least one of a surfactant, a solid diluent or a liquid diluent. Other bioactive compounds or agents can be incorporated into compositions comprising at least one of a surfactant, a solid or liquid diluent. In the case of the mixture of the present invention, a premix can be formed by combining one or more other biologically active compounds or agents with the compound of Formula 1, or one or more other biologically active compounds or agents can be combined separately with the compound of Formula 1, and this mixture can be combined or applied sequentially before application (for example, in a spray tank).

[0152] A mixture of one or more of the following herbicides and the compound of the present invention may be particularly useful for weed control: acetochlor, acyfluorphen and its sodium salt, acroniphen, acrolein (2-propenal), alachlor, alloxidim, ametrin, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)-2-pyridinecarbone 2-Propyn-1-yl ester (CAS No.: 2251111-17-6), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)-2-pyridinecarboxylate cyanomethyl ester (CAS No.: 2251111-18-7), aminopyralide, amitorol, ammonium amidosulfate, 2,5-anhydro-3,4-dideoxy-4-[[[(5S)-3-(3,5-difluorophenyl)-5-ethenyl-4,5-dihydro-5-isoxazolyl]carbonyl]amino] -Threo-pentonate methyl ester (CAS number: 27499989-21-6), anirofos, anisifurupurine, ashram, atrazine, azimusulfuron, bixzolon, beflubutamide, beflubutamide-M, benazoline, benazoline ethyl, bencarbazone, benfluralin, benfresate, benkytrione, bensulfuron methyl, benslid, bentazon, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bialafos, bispiribac and its sodium salt, bromacil, bromacil Mobutide, bromophenoxime, bromoxynyl, bromoxynyl octanoate, butachlor, butaphenacil, butamiphos, butruarin, butroxidime, butyrate, bipirazone, cafenstrol, carbetamide, 1-(2-carboxyethyl)-4-(2-pyrimidinyl)pyridazinium (CAS No.: 2285384-11-2) and its salts, carfentrazon ethyl, catechin, clomethoxyfen, chloramben, chlorbromulone, chlorflurenol methyl, chloridazone, chlorimurone ethyl,3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazole carboxylate ethyl ester (CAS number: 1949837-17-5), chlorotolurone, chlorpropham, chlorsulfuron, chlortaldimethyl, chlorthiamide, synidone ethyl, sinmethyline, cinosulfuron, crasiphos, crehoxidim, cretodim, clodinahoppropargyl, chromazon, clomeprop, Clopyralide, clopyralide-olamine, chloranthrummethyl, cumylon, cyanazine, cycloate, cyclopyrimolate, cyclosulfamurone, cycloxidymium, cyhalofop-butyl, 2,4-D and its butyl, isooctyl and isopropyl esters and their dimethylammonium, diolamine and trolamine salts, ciprafluon, dimuron, darapon, darapon sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedifam, desmethrin, dicamba and its dimeth Ammonium, potassium and sodium salts, diclobenyl, dichlorprop, diclohop-methyl, diclothram, diphenzocoat methyl sulfate, diflufenican, diflufenzopyr, dimeflon, dimepiperate, dimesulfazet, dimethachlor, dimethametrin, dimethenamide, dimethenamide-P, dimethipine, dimethylarsinic acid and its sodium salts, dinitramine, dinoterb, dioxopyritrone, diphenamide, diquat dibromide, dithiopyr, diuron, DNOC, endotal, EPTC, epiriphenacil, esp Locarb, Etalfluralin, Etamethosulfuron Methyl, Ethidine, Etofmesate, Ethoxyfen, Ethoxysulfuron, Etobenzanide, Phenoxaprop Ethyl, Phenoxaprop-P-Ethyl, Phenoxasulfone, Fenpyrazone, Fenquinotrione, Fentrazamide, Fenuron, Fenuron-TCA, Flamprop-Methyl, Flamprop-M-Isopropyl, Flamprop-M-Methyl, Flazasulfuron, Floraslam, Fluadifop-Butyl, Fluadifop-P-Butyl, Fluazolate, Flucarbazone,Flucetosulfuron, fluchloralin, fluchloraminopyr, fluphenacet, fluphenoximacil, flufenpyr, flufenpyr ethyl, flumetulam, flumicrolacpentyl, flumioxazine, fluomethron, fluoroglycofen ethyl, flupoxam, flupyrsulfuron methyl and its sodium salt, flurenol, flurenol butyl, flulidone, flulochloridone, fluroxypyr, flulutamone, flusulfinum, fluthiaset methyl, fomesafen, folamsulfuron, fosamine ammonium, glufosine Salts of glufosinate ammonium, glufosinate-P, glyphosate and its ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimethium (also known as sulfosate), halaxifene, halaxifene methyl, halosulfuron methyl, haloxyhop ethotyl, haloxyhop methyl, hexazinone, hydantosidine, imazametabenz methyl, imazamox, imazapick, imazapyr, imazakine, imazakine ammonium, imazesapir, imazesapir ammonium, imazos Ruflon, Indanophan, Indadiflame, Iofensulflon, Iodosulfuron-methyl, Ioxinyl, Ioxinyloctanoate, Ioxinylsodium, Ipfencarbazone, Isoprotulon, Isouron, Isoxaben, Isoxaflutol, Isoxachlortol, Lactofen, Renacil, Linuron, Hydrazide Maleate, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium salt and MCPA-sodium salt, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl)) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron methyl, mesotrione, metam sodium salt, metamihop, metamitron, metazachlor, metazosulfuron, metabenzuthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldimuron, metobenzuron, metobromulone, metrachlor,S-Metrachlor, Methoslam, Methoxlon, Metrivudine, Methosulfuron-methyl, Molinate, Monolinuron, Naproanilide, Napropamide, Napropamide-M, Naptaram, Nevron, Nicosulfuron, Norflurazone, Olbencarb, Orthosulfamuron, Oryzalin, Oxaziargyl, Oxadiazone, Oxasulfuron, Oxadiclomefone, Oxyflofen, Paraquat dichloride, Pebrate, Pelargonic acid, Pendimethalin, Penoxslam, Pentanoclor, Pentoxazone, Perfluidone, Petoxamide Petoxyamide, Fenmedifam, Pichloram, Pichloram Potassium, Picolinafene, Pinoxadene, Piperophos, Pretilachlor, Primisulfuron Methyl, Prodiamine, Profoxidim, Prometon, Prometrin, Propacrol, Propanil, Propaxafop, Propazine, Profam, Propisochlor, Propoxycarbazone, Propyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen Ethyl, Pyrasulfol, Pyrazogyl, Pyrazolinate, Pyrazoxiphen, Pyrazosulf Ron-ethyl, pyribenzoxime, pyributicarb, pyridate, pyriflubenzoxime, pyriftalide, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac sodium salt, pyroxasulfone, piroxulam, quinchlorac, quinmelac, quinoclamin, quizalophop-ethyl, quizalophop-P-ethyl, quizalophop-P-tefuryl, limisoxafen, limsulfuron, saflufenacil, cethoxydim, siduron, simazine, simetryn, sulcotrione, sulfenthrazone, sulfomethanemethyl, sulfosulf Ron, 2,3,6-TBA, TCA, TCA-sodium, Tebutam, Tebuthiurone, Tefuryltrione, Tempotrione, Tepraloxidim, Terbasil, Terbumetone, Terbutyrazine, Terbutrin, Tetoflupyrrolimet, Tenylchlor, Thiazopyr, Thiencarbazone, Thifensulfuron-methyl, Thiobencarb, Thiafenasil, Thiocarbazil, Tolpyralate, Topramesone, Tralcoxidim, Trialate, Triafamone, Triasulfuron, Triaziflame, Tribenulon-methyl, Triclopyr, Triclopyr-butotyl,Triclopyr-triethylammonium, tridiphan, trietadine, trifloxysulfuron, trifludimoxazine, trifluralin, triflusulfuronmethyl, tripyrulfone, tritosulfuron, burnalate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridine-2(1H)-one, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexene-1 -yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1-methyl-1H-tetrazole-5-yl)-6-(trifluoromethyl)-3-dioneoxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazine-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy C-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (formerly known as methioxoline), 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 4- Methyl amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazole-5-yl)-4-(trifluoromethyl)benzamide, and 2-methyl-N-(4-methyl-1,2,5-oxadiazole-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides include Alternaria destruens (Simmons), Colletotrichum gloeosporiodes (Penz.) Penz.&Sacc., and Drexera monoceras (MTB-951).Examples of biological herbicides include Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl., and Puccinia thlaspeos (Schub.).

[0153] For better control of undesirable vegetation (e.g., by reducing the amount used through enhanced effectiveness, broader weed spectrum, or improved crop safety) or to prevent the emergence of resistant weeds, a mixture of the compound of the present invention with a herbicide selected from the group consisting of: atrazine, azimsulfuron, S-beflubutamide, benzisothiazolinone, carfentrazon-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, chromazon, clopyralidopotassium, chloranslam-methyl, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, 2-[(2,5-dichlorophenyl)methyl]-4,4 -Dimethyl-3-isoxazolidinone, etametsulfuron-methyl, flumetulam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,4H)-dione, flupirsulfuron-methyl, fluthiaset-methyl, homesafen, imazetapyr, lenacil, mesotrione, metrivudine, metusulfuron-methyl, petoxamide, picrolam, pyroxasulfone, quinchlorac, limsulfuron, S-methrachlor, sulfenthrazone, thifensulfuron-methyl, triflusulfuron-methyl, and tribenulon-methyl.

[0154] The compounds of the present invention may also be used in combination with plant growth regulators, such as abiglycine, N-(phenylmethyl)-1H-purine-6-amine, epocholeon, gibberellic acid, gibberellin A4 and A7 harpin proteins, mepicote chloride, prohexadione calcium salt, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and organisms that regulate plant growth, such as Bacillus cereus BP01 strain.

[0155] General references on agricultural protective agents (i.e., herbicides, herbicide phytotoxicity reducers, insecticides, fungicides, nematicides, acaricides, and biological agents) include The Pesticide Manual, 13th Edition, CDSTomlin, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2003 and The BioPesticide Manual, 2nd Edition, LGCopping, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2001.

[0156] In embodiments where one or more of these various mixing partners are used, the mixing partner is typically used in amounts equivalent to those conventionally used when the mixing partner is used alone. More specifically, in many cases, the active ingredient in the mixture is applied in amounts ranging from half to the full amount specified on the product label when the active ingredient is used alone. These amounts are described in references such as The Pesticide Manual and The BioPesticide Manual. The weight ratio of these various mixing partners (total) to the compound of Formula 1 is typically about 1:3000 to about 3000:1. Ratios of about 1:300 to about 300:1 (e.g., about 1:30 to about 30:1) are particularly noteworthy. Those skilled in the art can easily determine the biologically effective amount of the active ingredient required to obtain the desired bioactivity spectrum by simple experiments. It will be apparent that by including these additional components, the spectrum of controllable weeds can be expanded beyond the spectrum controlled by the compound of Formula 1 alone.

[0157] In certain cases, combining the compounds of the present invention with other biologically active (particularly herbicidal) compounds or agents (i.e., active ingredients) can yield a greater-than-additive (i.e., enhanced) effect against weeds and / or a smaller-than-additive (i.e., reduced phytotoxicity) effect against crops or other desirable plants. It is always desirable to reduce the amount of active ingredients released into the environment while ensuring effective pest control. It is also desirable to be able to use larger amounts of active ingredients to achieve more effective weed control without causing excessive damage to crops. If the effect of the herbicide mixture of active ingredients on weeds is enhanced at application rates that yield an agriculturally satisfactory level of weed control, such combinations can be advantageous in reducing crop protection costs and environmental impact. If the phytotoxicity of the herbicidal active ingredient on crops is reduced, such combinations can be advantageous in improving crop protection by reducing competition with weeds.

[0158] Of particular note are the combinations of the compound of the present invention with at least one other herbicidal active ingredient. Of such combinations, those in which the other herbicidal active ingredient has a different site of action from the compound of the present invention are of particular note. In certain examples, a combination with at least one other herbicidal active ingredient having a similar control spectrum but a different site of action would be particularly advantageous for managing resistance. Therefore, the composition of the present invention may further contain (in an effective herbicidal amount) at least one additional herbicidal active ingredient having a similar control spectrum but a different site of action.

[0159] The compounds of the present invention are used to improve the safety of specific crops as herbicide phytotoxicity reducers, such as aridocrol, benoxacol, croquintoset-mexyl, cumylon, siomethrinyl, cyprosulfonamide, dimuron, dichlormid, dicyclonone, diethrate, dimepiperate, fenchlorazole-ethyl, fenchlorim, flurazole, fluxofenim, flirazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride (1,8-naphthalic anhydride), oxavethrinyl, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON It can also be used in combination with 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, 3-oxo-1-cyclohexen-1-yl 1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone, and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide. An effective amount of herbicide phytotoxicity reducer can be applied simultaneously with the compounds of the present invention or as a seed treatment. Accordingly, aspects of the present invention relate to herbicide mixtures comprising the compound of the present invention and an effective amount of herbicide-reducing agent. Seed treatment is particularly useful for selective weed control because detoxification to crop plants is physically limited. Accordingly, a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesirable vegetation in a crop, comprising contacting the crop habitat with an effective amount of the compound of the present invention, wherein the seeds from which the crop grows are treated with an effective amount of the herbicide-reducing agent.Those skilled in the art can easily determine the effective antidote dose of a drug-induced harm reduction agent by conducting a simple experiment.

[0160] The compounds of the present invention may also be mixed with: (1) polynucleotides (not limited to DNA, RNA and / or chemically modified nucleotides) that affect the amount of a specific target by downregulating, interfering with, repressing or silencing gene-derived transcripts, thereby conferring a herbicidal effect; or (2) polynucleotides (not limited to DNA, RNA and / or chemically modified nucleotides) that affect the amount of a specific target by downregulating, interfering with, repressing or silencing gene-derived transcripts, thereby conferring a phytotoxicity reduction effect.

[0161] Of particular note is the composition comprising the compound of the present invention (in an effective amount for herbicidal control), at least one additional active ingredient (in an effective amount) selected from the group consisting of other herbicides and herbicide damage reducers, and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents.

[0162] Table A1 describes specific combinations of component (a) and component (b) illustrating the mixtures, compositions, and methods of the present invention. The compound number (i.e., compound 1) in the component (a) column can be found in Index Table A. The second column of Table A1 lists the specific compound of component (b) (for example, "2,4-D" in the first column). The third, fourth, and fifth columns of Table A1 describe the range of weight ratios of the compound of component (a) to component (b) (i.e., (a):(b)) based on typical application rates when applied to field crops. Thus, for example, the first column of Table A1 specifically discloses that the combination of component (a) (i.e., compound 1 in Index Table A) and 2,4-D is typically applied in a weight ratio of 1:384 to 6:1. The remaining columns of Table A1 are interpreted similarly.

[0163] [Table 23]

[0164] Table 24

[0165] Table 25

[0166] Table 26

[0167] Table 27

[0168] Table 28

[0169] Table 29

[0170] Table 30

[0171] Table 31

[0172] Table 32

[0173] Table A2 has the same structure as Table A1 above, except that the information under the heading of the "Component (a)" column is replaced with the respective information in the Component (a) column shown below. The compound numbers in the Component (a) column are identified in Index Table A. Therefore, for example, in Table A2, the information under the heading of the "Component (a)" column is always written as "Compound 2" (i.e., Compound 2 identified in Index Table A), and the first column under the heading of the column in Table A2 specifically discloses a mixture of Compound 2 and 2,4-D. Tables A3 to A204 have a similar structure.

[0174] [Table 33]

[0175] [Table 34]

[0176] [Table 35]

[0177] To better control undesirable vegetation (for example, by reducing the amount used through enhanced effectiveness, broadening the spectrum of controlled weeds, or improving crop safety) or to prevent the emergence of resistant weeds, a mixture of the compound of the present invention with a herbicide selected from the group consisting of chlorimulone-ethyl, nicosulfuron, mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribeurone, pyroxasulfone, pinoxadene, tembotrione, pyroxlam, metrachlor, and S-metrachlor is preferred.

[0178] The following tests demonstrate the control effect of the compounds of the present invention against specific pathogens. However, the protection made possible by pathogen control with these compounds is not limited to these species. For a description of the compounds, please refer to the following index tables A to H. The abbreviation "Cmpd." represents "compound," the abbreviation "Ex." represents "example," and the following number indicates the example in which the compound was prepared. The values ​​reported in the "MS" column are the molecular weight of the positively charged parent ion (M+1) with the highest isotopic abundance, formed by adding H+ (molecular weight 1) to the molecule with the highest isotopic abundance, or the molecular weight of the positively charged parent ion (M+23) with the highest isotopic abundance, formed by adding Na+ (molecular weight 23), or the molecular weight of the negatively charged ion (M-1) with the highest isotopic abundance, formed by losing H+ (molecular weight 1). "Pyr" means "pyridine." "Przl" means "pyrazole." "Thzl" means "thiazole". "Trzl" means "triazole". "Imdzl" means "imidazole". "c-pent" means "cyclopentyl". One or more isotopes with a lower isotopic abundance and a higher atomic weight (for example, 37 Cl, 81 The presence of molecular ions containing Br) is not reported. The reported MS peaks were observed by mass spectrometry using electrospray ionization (ESI) or atmospheric pressure chemical ionization (APCI). "Stereochemical configuration (*)" indicates the stereochemical configuration at the position marked with an asterisk ("*").

[0179] [Table 36]

[0180] [Table 37]

[0181] [Table 38]

[0182] Table 39

[0183] Table 40

[0184] Table 41

[0185] Table 42

[0186] Table 43

[0187] Table 44

[0188] Table 45

[0189] Table 46

[0190] Table 47

[0191] Table 48

[0192] [Table 49]

[0193] [Table 50]

[0194] [Table 51]

[0195] [Table 52]

[0196] [Table 53]

[0197] Biological embodiments of the present invention Test A Echinochloa crus-galli, Alopecurus myosuroides, Zea mays, giant foxtail (Setaria faberi), Setaria viridis, Eleusine indica, Bassia scoparia, wild oat (Avena fatua), palmer amaranth (Amaranthus palmeri), common ragweed (Ambrosia artemisiifolia), Italian ryegrass (Lolium multiflorum), soybean (Glycine max), and wheat (Triticum). Seeds of plant species selected from *Aestivum* were sown in a soil mixture of loam and sand, and treated with a test compound formulated in a non-phytotoxic solvent mixture containing a surfactant by directional soil spraying before germination.

[0198] Simultaneously, in addition to the plants selected from these crops and weed species, catchweed bedstraw (Galium aparine) and dwarf confectionery (Erigeron canadensis) were planted in pots containing the same loamy soil and sand mixture, and treated with similarly formulated test compounds by post-emergence application. At the time of post-emergence treatment, the plants were 2-10 cm tall and at the 1-2 leaf stage. Treated plants and untreated controls were kept in a greenhouse for 10 days, after which all treated plants were compared to the untreated controls, and damage was visually assessed. The evaluation of plant responses summarized in Table A is based on a scale of 0-100, where 0 is no effect and 100 is complete control. A dash (-) indicates that there is no test result.

[0199] [Table 54]

[0200] [Table 55]

[0201] [Table 56]

[0202] Table A Compounds 500g Active ingredient / ha 176 Before germination Barnyard grass 100 Wild sparrow's gun 100 Corn 100 Foxtail grass 100 Kochia 100 Wild oats 90 Ragweed 0 Ricegrass 100 Soybeans 80 Wheat 100

[0203] [Table 57]

[0204] [Table 58]

[0205] [Table 59]

[0206] [Table 60]

[0207] [Table 61]

[0208] Table 62

[0209] Table 63

[0210] Table 64

[0211] Table 65

[0212] Table 66

[0213] Table 67

[0214] Table 68

[0215] Table 69

[0216] Table 70

[0217] Table 71

[0218] Table 72

[0219] Table 73

[0220] Table 74

[0221] Table 75

[0222] Table 76

[0223] Table 77

[0224] Table 78

[0225] Table 79

[0226] Table 80

[0227] Table 81

[0228] Table 82

[0229] Table 83

[0230] Table 84

[0231] Table 85

[0232] Table 86

[0233] Table 87

[0234] Table 88

[0235] Table 89

[0236] Table 90

[0237] Table 91

[0238] Table 92

[0239] Table 93

[0240] Table 94

[0241] Table 95

[0242] Table 96

[0243] Table 97

[0244] Table 98

[0245] Table 99

[0246] Table 100

[0247] Table 101

[0248] Table 102

[0249] Table 103

[0250] [Table 104]

[0251] [Table 105]

[0252] [Table 106]

[0253] [Table 107]

[0254] [Table 108]

[0255] [Table 109]

[0256] [Table 110]

[0257] Test B In the flooded paddy field experiment, plant species selected from barnyard grass (Echinochloa crus-galli), black-veined rice (Heteranthera limosa), weed rice (Oryza sativa), and small-flower umbrella sedge (Cyperus difformis) were grown to the two-leaf stage for the experiment. For treatment, test pots were flooded to a depth of 3 cm from the soil surface, and the test compound was applied directly to the flooded water. The water depth was then maintained throughout the experiment. Treated plants and controls were kept in a greenhouse for 13 days, after which all plant species were visually evaluated in comparison to the controls. The plant response evaluations summarized in Table B are based on a 0-100 scale, where 0 represents no effect and 100 represents complete control. A dash (-) indicates that there is no test result.

[0258] [Table 111]

[0259] [Table 112]

[0260] [Table 113]

[0261] [Table 114]

[0262] [Table 115]

[0263] [Table 116]

[0264] Table 117

[0265] Table 118

[0266] Table 119

[0267] Table 120

[0268] Table 121

[0269] Table 122

Claims

1. Formula 1 【Chemistry 1】 (In the formula, Y is either O or NH, Z is optionally R ｖ The following groups of fully saturated or fully or partially unsaturated five-membered rings that are substituted by a group 【Chemistry 2】 Selected from, m is 0, 1, or 2. R ｖ These are halogens, cyanoacrylate, CO2 ２ R ８ or (C １ ~C ２ )-alkyl or (C １ ~C ２ )-alkoxy, each of which is substituted by n groups independently selected from the group consisting of halogens, Each R is independently H, halogen, cyano, nitro, hydroxy, C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl, C ３ to C ７ cycloalkyl, C ３ to C ７ halocycloalkyl, C １ to C ６ alkoxy, C １ to C ６ haloalkoxy, S(O) ｐ R ７ or CO ２ R ８ and is n is 0, 1, 2, 3, 4, or 5. p is 0, 1, or 2. V and W are independently O or S, X is a direct bond, O, S or NR ６ And, R １ and R ２ These are, independently, hydrogen, halogen, cyano, and C. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Cyanoalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy or C １ ~C ６ It is a cyanoalkoxy, R ３ is H, halogen, cyano, nitro, hydroxy, C １ -C ６ -C ２ -C ５ -alkenyl, C ２ -C ５ -alkynyl, C ２ -C ５ -alkenyloxy, C ２ -C ５ -alkynyloxy, C ３ -C ７ -cycloalkoxy, C ３ -C ７ -cycloalkoxyalkyl, C ３ -C ６ -cycloalkyl, C ４ -C ７ -cycloalkylalkyl, C １ -C ６ -haloalkyl, C ２ -C ５ -haloalkenyl, C ２ -C ５ -haloalkynyl, C ２ -C ５ -alkoxyalkyl, C ２ -C ５ -haloalkoxyalkyl, C １ -C ５ -alkoxy, C １ -C ６ -haloalkoxy, C １ -C ５ -alkylthio, C １ -C ４ -alkylsulfinyl, C １ -C ４ -alkylsulfonyl, C １ -C ４ -alkylsulfonate, C １ -C ４ -haloalkylthio, C １ -C ４ -haloalkylsulfinyl, C １ -C ４ -haloalkylsulfonyl or C ２ -C ５ -alkoxycarbonyl, and optionally, each of these is halogen, cyano, C １ -C ４ Alkoxy, C １ ~C ５ Alkylthio, C １ ~C ４ Alkyl sulfinyl, C １ ~C ４ It is further substituted with at least one group from the group consisting of alkylsulfonyl and hydroxyl, R ４ H and C are independent of each other. １ ~C ６ Alkyl, C ３ ~C ７ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy or W １ G １ And, W １ Direct bond, C １ ~C ４ Alkandiil or C １ ~C ４ He is an Arkenzil, G １ is S(O) ｐ R ７ SO ２ NR １０ R １１ CO ２ R ８ CONR １０ R １１ or COR １２ And, R ５ H, C １ ~C １２ Alkyl, NH ２ N=CR ８ R １２ , C ３ ~C ７ Cycloalkyl, C ３ ~C １２ Cycloalkylalkyl, C ２ ~C ８ Alkenil, C ５ ~C ６ Cycloalkenyl, C ２ ~C ８ Alkinyl, (CH ２ ) ｑ S(O) ｐ R ７ , (CH ２ ) ｑ OR ９ , (CH ２ ) ｑ COR １２ And each of these is a halogen, cyano, C １ ~C ６ Alkyl, C １ ~C ６ It is optionally substituted with one or more groups from the group consisting of alkoxy, hydroxy, and aryl. q is 0, 1, 2, 3, 4, or 5. R ６ is hydrogen, cyano, OR ９ , S(O) ｐ R ７ SO ２ NR １０ R １１ CO ２ R ８ CONR １０ R １１ COR １２ , NR １０ R １１ , NR １０ COR １２ , NR １０ CONR １０ R １１ , NR １０ CO2R ８ , NR １０ SO ２ R ７ , NR １０ SO2NR １０ R １１ , C(R ７ ) = NOR ９ , an optionally substituted aryl, an optionally substituted heteroaryl, or an optionally substituted heterocycline, R ６ C １ ~C １２ Alkyl, C ３ ~C ８ Cycloalkyl, C ４ ~C １２ Cycloalkylalkyl, C ２ ~C １２ Alkenil, C ５ ~C ７ Cycloalkenyl or C ２ ~C １２ These are alkynyls, and each of them is a halogen, cyano, nitro, OR ９ , S(O) ｐ R ７ SO ２ NR １０ R １１ CO ２ R ８ CONR １０ R １１ COR １２ , NR １０ R １１ , NR １０ COR １２ , NR １０ CONR １０ R １１ , NR １０ CO ２ R ８ , NR １０ SO ２ R ７ , NR １０ SO ２ NR １０ R １１ , C(R ７ ) = NOR ９ , or, optionally substituted with one or more groups from the group consisting of optionally substituted aryls, optionally substituted heteroaryls, or optionally substituted heterocyclines, R ５ and R ６ These, together with the nitrogen atoms to which they are bonded, can form a 3- to 7-membered ring containing a carbon atom and optionally 1 to 3 oxygen, sulfur, or nitrogen atoms as ring members, where up to two carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is S, S(O), or S(O). ２ Selected from, the ring is halogen, cyano, nitro, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, OR ９ , S(O) ｐ R ７ SO ２ NR １０ R １１ CO ２ R ８ CONR １０ R １１ COR １２ , NR １０ R １１ , NR １０ COR １２ , NR １０ CONR １０ R １１ , NR １０ CO ２ R ８ , NR １０ SO ２ R ７ , NR １０ SO ２ NR １０ R １１ , C(R ７ ) = NOR ９ It is optionally substituted with at least one substituent independently selected from the group consisting of the following: R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are H and C, respectively, independently. １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkyl, C ３ ~C ７ They are cycloalkyl or aryl, each of which is F, Cl, C １ ~C ２ (Optionally substituted with one or more groups from the group consisting of alkoxy or aryl molecules.) Compounds of the same species, all of its stereoisomers, N-oxides, and salts.

2. Y is O, Z-A is selected from Z-1 to Z-29, Z-B is selected from Z-30 to Z-62, Z-C is selected from Z-63 to Z-64, and Z-D is selected from Z-65 to Z-74. 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 Selected from, m is either 0 or 1. R is independently H, halogen, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy or C １ ~C ６ It is a haloalkoxy, n is 1, 2, or 3. R １ and R ２ These are, independently, hydrogen, halogen, cyano, and C. １ ~C ３ Alkyl, C １ ~C ３ Haloalkyl, C １ ~C ３ Cyanoalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy or C １ ~C ３ It is a cyanoalkoxy, and R ３ H, halogen, cyano, hydroxy, C １ ~C ３ Alkyl, C ２ ~C ３ Alkenil, C ２ ~C ３ Alkinyl, C ３ ~C ５ Cycloalkoxy, C ３ ~C ５ Cycloalkoxyalkyl, C ３ ~C ５ Cycloalkyl, C ４ ~C ７ Cycloalkylalkyl, C １ ~C ３ Haloalkyl, C ２ ~C ３ Alkoxyalkyl, C ２ ~C ３ Haloalkoxyalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy, C １ ~C ３ Alkylthio, C １ ~C ３ Alkyl sulfinyl or C １ ~C ３ The compound according to claim 1, wherein it is an alkylsulfonyl compound.

3. Z is selected from the group Z-A, R is independent of H, F, Cl, Br, cyano, and C. １ ~C ２ Alkyl, C １ ~C ２ Haloalkyl, C １ ~C ２ Alkoxy or C １ ~C ２ It is a haloalkoxy, Both V and W are O. X is either O or S, R ３ H, C １ ~C ３ Alkyl, C ２ ~C ３ Alkenil, C ２ ~C ３ Alkinyl, C ３ ~C ５ Cycloalkyl, C ４ ~C ７ Cycloalkylalkyl, C １ ~C ３ Haloalkyl, C ２ ~C ３ Alkoxyalkyl, C ２ ~C ３ Haloalkoxyalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ It is a haloalkoxy, R ４ H, C １ ~C ６ Alkyl, C ３ ~C ７ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ It is a haloalkoxy, and R ５ H, C １ ~C １２ Alkyl, NH ２ N=CR ８ R １２ , C ３ ~C ７ Cycloalkyl, C ３ ~C １２ Cycloalkylalkyl, C ２ ~C ８ Alkenil, C ５ ~C ６ Cycloalkenyl, C ２ ~C ８ Alkinyl, (CH ２ ) ｑ S(O) ｐ R ７ , (CH ２ ) ｑ OR ９ , (CH ２ ) ｑ COR １２ And each of these is a halogen, cyano, C １ ~C ６ Alkyl, C １ ~C ６ The compound according to claim 2, which is optionally substituted with one or more groups from the group consisting of alkoxy, hydroxy, and aryl.

4. Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24. R is independent of H, F, Cl, Me, CF ３ , OMe or OCF ３ And, n is 2, R is in 3rd and 5th place. R １ and R ２ These are, independently, hydrogen, halogen, cyano, Me, and CF. ３ ,CH ２ CN, OMe, OCF ３ or OCH ２ It is CN, R ３ is H, Me, Et, CH=CH ２ , C≡CH, cyclopropyl, cyclopropylmethicone, CF ３ , OMe or OCF ３ And, R ５ are H, Me, Et, c-Pr, c-Bu, CH ２ -c-Pr, (CH ２ ) ｑ S(O) ｐ Me, (CH ２ ) ｑ OMe, (CH ２ ) ｑ COMe is a compound, and each of these is F, Cl, cyano, C １ ~C ３ Alkyl, C １ ~C ３ It is optionally substituted with one or more groups from the group consisting of alkoxy, hydroxy, and Ph, and R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are H and C, respectively, independently. １ ~C ３ Alkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkyl, C ３ ~C ５ They are cycloalkyl or phenyl, each of which is F, Cl, C １ ~C ２ The compound according to claim 3, which is optionally substituted with one or more groups from the group consisting of alkoxy or aryl groups.

5. Z is selected from the group Z-A, R is independent of H, F, Cl, Br, cyano, and C. １ ~C ２ Alkyl, C １ ~C ２ Haloalkyl, C １ ~C ２ Alkoxy or C １ ~C ２ It is a haloalkoxy, Both V and W are O. X is NR ６ And, R ３ H, C １ ~C ３ Alkyl, C ２ ~C ３ Alkenil, C ２ ~C ３ Alkinyl, C ３ ~C ５ Cycloalkyl, C ４ ~C ７ Cycloalkylalkyl, C １ ~C ３ Haloalkyl, C ２ ~C ３ Alkoxyalkyl, C ２ ~C ３ Haloalkoxyalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ It is a haloalkoxy, R ４ H, C １ ~C ６ Alkyl, C ３ ~C ７ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ The compound according to claim 2, wherein it is a haloalkoxy.

6. Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24. R is independent of H, F, Cl, Me, CF ３ , OMe or OCF ３ And, n is 2, R is in 3rd and 5th place. R １ and R ２ These are, independently, hydrogen, halogen, cyano, Me, and CF. ３ ,CH ２ CN, OMe, OCF ３ or OCH ２ It is CN, R ３ is H, Me, Et, CH=CH ２ , C≡CH, cyclopropyl, cyclopropylmethicone, CF ３ , OMe or OCF ３ and R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are H and C, respectively, independently. １ ~C ３ Alkyl, C １ ~C ３ Haloalkyl, C ３ ~C ５ They are cycloalkyl or phenyl, each of which is F, Cl, C １ ~C ２ The compound according to claim 5, which is optionally substituted with one or more groups from the group consisting of alkoxy or aryl groups.

7. R ５ and R ６ These can, together with the nitrogen atom to which they are bonded, form a 3- to 7-membered ring, the 3- to 7-membered ring containing a carbon atom and optionally 1-2 oxygen, sulfur, or nitrogen atoms as ring members, the maximum of 2 carbon atom ring members being independently selected from C(=O) and C(=S), and the sulfur atom ring member being S, S(O), or S(O) ２ Selected from, the ring is halogen, cyano, C １ ~C ３ Alkyl, C １ ~C ３ The compound according to claim 5, which is optionally substituted with at least one substituent independently selected from the group consisting of haloalkyl groups.

8. Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24. R is independent of H, F, Cl, Me, CF ３ , OMe or OCF ３ And, n is 2, R is in 3rd and 5th place. R １ and R ２ These are, independently, hydrogen, halogen, cyano, Me, and CF. ３ ,CH ２ CN, OMe, OCF ３ or OCH ２ It is CN, R ３ is H, Me, Et, CH=CH ２ , C≡CH, cyclopropyl, cyclopropylmethicone, CF ３ , OMe or OCF ３ and R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are H and C, respectively, independently. １ ~C ３ Alkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkyl, C ３ ~C ５ They are cycloalkyl or phenyl, each of which is F, Cl, C １ ~C ２ The compound according to claim 7, which is optionally substituted with one or more groups from the group consisting of alkoxy or aryl groups.

9. Z is selected from the group Z-B, R is independent of H, F, Cl, Br, cyano, and C. １ ~C ２ Alkyl, C １ ~C ２ Haloalkyl, C １ ~C ２ Alkoxy or C １ ~C ２ It is a haloalkoxy, Both V and W are O. X is either O or S, R ３ H, C １ ~C ３ Alkyl, C ２ ~C ３ Alkenil, C ２ ~C ３ Alkinyl, C ３ ~C ５ Cycloalkyl, C ４ ~C ７ Cycloalkylalkyl, C １ ~C ３ Haloalkyl, C ２ ~C ３ Alkoxyalkyl, C ２ ~C ３ Haloalkoxyalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ It is a haloalkoxy, R ４ H, C １ ~C ６ Alkyl, C ３ ~C ７ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ It is a haloalkoxy, and R ５ H, C １ ~C １２ Alkyl, NH ２ N=CR ８ R １２ , C ３ ~C ７ Cycloalkyl, C ３ ~C １２ Cycloalkylalkyl, C ２ ~C ８ Alkenil, C ５ ~C ６ Cycloalkenyl, C ２ ~C ８ Alkinyl, (CH ２ ) ｑ S(O) ｐ R ７ , (CH ２ ) ｑ OR ９ , (CH ２ ) ｑ COR １２ And each of these is a halogen, cyano, C １ ~C ６ Alkyl, C １ ~C ６ The compound according to claim 2, which is optionally substituted with one or more groups from the group consisting of alkoxy, hydroxy, and aryl.

10. Z is Z-30, Z-34, Z-36, Z-42, Z-47, Z-48, Z-53, Z-54, Z-55, Z-57 or Z-62, R is independent of H, F, Cl, Me, CF ３ , OMe or OCF ３ And, n is 2, R is in 3rd and 5th place. R １ and R ２ These are, independently, hydrogen, halogen, cyano, Me, and CF. ３ ,CH ２ CN, OMe, OCF ３ or OCH ２ It is CN, R ３ is H, Me, Et, CH=CH ２ , C≡CH, cyclopropyl, cyclopropylmethyl, CF ３ , OMe or OCF ３ And, R ５ are H, Me, Et, c-Pr, c-Bu, CH ２ -c-Pr, (CH ２ ) ｑ S(O) ｐ Me, (CH ２ ) ｑ OMe, (CH ２ ) ｑ COMe is a compound, and each of these is F, Cl, cyano, C １ ~C ３ Alkyl, C １ ~C ３ It is optionally substituted with one or more groups from the group consisting of alkoxy, hydroxy, and Ph, and R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are H and C, respectively, independently. １ ~C ３ Alkyl, C １ ~C ３ Haloalkyl, C ３ ~C ５ They are cycloalkyl or phenyl, each of which is F, Cl, C １ ~C ２ The compound according to claim 9, which is optionally substituted with one or more groups from the group consisting of alkoxy or aryl groups.

11. (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2,2,2-trifluoroethyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2,2,2-trifluoroethyl, (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-(methylthio)ethyl, (4S)-4-[[[(5S)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (4S)-4-[[[(5R)-3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylate methyl, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid 1-methylethyl, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate methyl, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid 2-methylpropyl, (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid, (4S)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-1-cyclopentene-1-carboxylic acid, (1S,4R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylic acid, and (1S,4R)-4-[[[3-(3,5-difluorophenyl)-5-methyl-2-oxo-5-oxazolidinyl]carbonyl]amino]-2-cyclopentene-1-carboxylate ethyl A compound according to claim 1, selected from the group consisting of the following.

12. Y is NH, Z-A is Z-1 to Z-29 【Transformation 7】 【Transformation 8】 【Chemistry 9】 Selected from, m is either 0 or 1. R is independently H, halogen, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy or C １ ~C ６ It is a haloalkoxy, n is 1, 2, or 3. R １ and R ２ These are, independently, hydrogen, halogen, cyano, and C. １ ~C ３ Alkyl, C １ ~C ３ Haloalkyl, C １ ~C ３ Cyanoalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy or C １ ~C ３ It is a cyanoalkoxy, and R ３ H, halogen, cyano, hydroxy, C １ ~C ３ Alkyl, C ２ ~C ３ Alkenil, C ２ ~C ３ Alkinyl, C ３ ~C ５ Cycloalkoxy, C ３ ~C ５ Cycloalkoxyalkyl, C ３ ~C ５ Cycloalkyl, C ４ ~C ７ Cycloalkylalkyl, C １ ~C ３ Haloalkyl, C ２ ~C ３ Alkoxyalkyl, C ２ ~C ３ Haloalkoxyalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ Haloalkoxy, C １ ~C ３ Alkylthio, C １ ~C ３ Alkyl sulfinyl or C １ ~C ３ The compound according to claim 1, wherein it is an alkylsulfonyl compound.

13. Z is Z-1, Z-4, Z-6, Z-12, Z-22, or Z-24. R is independent of H, F, Cl, Br, cyano, and C. １ ~C ２ Alkyl, C １ ~C ２ Haloalkyl, C １ ~C ２ Alkoxy or C １ ~C ２ It is a haloalkoxy, Both V and W are O. X is either O or S, R ３ H, C １ ~C ３ Alkyl, C ２ ~C ３ Alkenil, C ２ ~C ３ Alkinyl, C ３ ~C ５ Cycloalkyl, C ４ ~C ７ Cycloalkylalkyl, C １ ~C ３ Haloalkyl, C ２ ~C ３ Alkoxyalkyl, C ２ ~C ３ Haloalkoxyalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ It is a haloalkoxy, R ４ H, C １ ~C ６ Alkyl, C ３ ~C ７ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ３ Alkoxy, C １ ~C ３ It is a haloalkoxy, and R ５ H, C １ ~C １２ Alkyl, NH ２ N=CR ８ R １２ , C ３ ~C ７ Cycloalkyl, C ３ ~C １２ Cycloalkylalkyl, C ２ ~C ８ Alkenil, C ５ ~C ６ Cycloalkenyl, C ２ ~C ８ Alkinyl, (CH ２ ) ｑ S(O) ｐ R ７ , (CH ２ ) ｑ OR ９ , (CH ２ ) ｑ COR １２ And each of these is a halogen, cyano, C １ ~C ６ Alkyl, C １ ~C ６ The compound according to claim 12, which is optionally substituted with one or more groups from the group consisting of alkoxy, hydroxy, and aryl.

14. R is independent of H, F, Cl, Me, CF ３ , OMe or OCF ３ And, n is 2, R is in 3rd and 5th place. R １ and R ２ These are, independently, hydrogen, halogen, cyano, Me, and CF. ３ ,CH ２ CN, OMe, OCF ３ or OCH ２ It is CN, R ３ is H, Me, Et, CH=CH ２ , C≡CH, cyclopropyl, cyclopropylmethicone, CF ３ , OMe or OCF ３ And, R ５ are H, Me, Et, c-Pr, c-Bu, CH ２ -c-Pr, (CH ２ ) ｑ S(O) ｐ Me, (CH ２ ) ｑ OMe, (CH ２ ) ｑ COMe is a compound, and each of these is F, Cl, cyano, C １ ~C ３ Alkyl, C １ ~C ３ It is optionally substituted with one or more groups from the group consisting of alkoxy, hydroxy, and Ph, and R ７ , R ８ , R ９ , R １０ , R １１ and R １２ These are H and C, respectively, independently. １ ~C ３ Alkyl, C １ ~C ３ Haloalkyl, C ３ ~C ５ They are cycloalkyl or phenyl, each of which is F, Cl, C １ ~C ２ The compound according to claim 13, which is optionally substituted with one or more groups from the group consisting of alkoxy or aryl groups.

15. A herbicide composition comprising a compound according to any one of claims 1 to 14 and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents.

16. The herbicide composition according to claim 15, further comprising at least one additional active ingredient selected from the group consisting of other herbicides and herbicide phytotoxicity reducers, and at least one ingredient selected from the group consisting of surfactants, solid diluents and liquid diluents.

17. (a) A compound according to any one of claims 1 to 14, and (b) (b1) a photosystem II inhibitor, (b2) an acetohydroxy acid synthase (AHAS) inhibitor, (b3) an acetyl-CoA carboxylase (ACCase) inhibitor, (b4) an auxin mimetic, (b5) a 5-enolpyruvicishikimic acid-3-phosphate (EPSP) synthase inhibitor, (b6) a photosystem I electron converter, (b7) a protoporphyrinogen oxidase (PPO) inhibitor, (b8) a glutamine synthase (GS) inhibitor, (b9) a very long-chain fatty acid (VLCFA) elongation enzyme inhibitor, (b10) an auxin transfer inhibitor, (b11) a phytoene desaturase (PDS) inhibitor, (b12) a 4-hydroxyphenylpyruvate dioxygenase (HPPD) (b1) inhibitors, (b13) homogentisic acid soranesyltransferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) dihydroorotic acid dehydrogenase (DHODH) inhibitors, (b16) mitotic inhibitors, organoarsenic compounds, ashrum, bromobutide, scinmethilin, cumylon, dazomet, diphenzocort, dimuron, etobenzanide, flurenol, hosamin, hosamin-ammonium, hydantosaidin, metam, methyldimuron, oleic acid, oxadiclomefone, pelargonic acid and pyributicarb, (b17) herbicide phytotoxicity reducers and herbicide mixtures comprising at least one additional active ingredient selected from salts of compounds (b1) to (b17).

18. A method for controlling the growth of undesirable vegetation, comprising contacting the vegetation or its environment with a compound according to any one of claims 1 to 14 in an amount effective for weed control.

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