Substituted pyridazinone herbicides

Abstract

Disclosed are compounds of formula 1 (including all stereoisomers, A-oxides, and salts thereof), pesticidal compositions containing them, and their use as herbicides, wherein R 1 , R 2 , R 3 , R 4 , R 14 and X are as defined herein, A is selected from A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, and A-11, and R 12 , R 13 , n, X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , Y and Y 1 is as defined in this disclosure. [Formula 1] TIFF2023554672000110.tif46170 [Case 2] TIFF2023554672000111.tif239170

Description

[Technical Field]

[0001] FIELD OF THE INVENTION The present invention relates to certain pyridazinone herbicides, their N-oxides, salts and compositions, and methods of their use to control undesirable vegetation. [Background technology]

[0002] Controlling undesirable vegetation is extremely important to achieve high yield efficiency. It is particularly desirable to achieve selective control of weed growth in useful crops such as rice, soybeans, sugar beets, corn, potatoes, wheat, barley, tomatoes, and plantation crops. Allowing weeds to grow in such useful crops can significantly reduce productivity, thereby resulting in increased costs for consumers. Controlling undesirable vegetation in non-cultivated areas is also important. Although many products for these purposes are available on the market, there remains a need for new compounds that are more effective, less costly, less toxic, environmentally safer, or have a different mechanism of action. Summary of the Invention [Means for solving the problem]

[0003] The present invention relates to compounds of formula 1, all stereoisomers, N-oxides and salts thereof, agricultural compositions containing them and their use as herbicides, [ka] During the ceremony, R 1is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or benzyl or phenyl (wherein the ring in said benzyl or phenyl group is not halogen, cyano, nitro, or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, the ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R 2 is H, halogen, cyano, formyl, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C 3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio or C2-C3 alkoxycarbonyl; or phenyl optionally substituted with halogen, C1-C4 alkyl or C1-C4 haloalkyl; R3 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or benzyl or phenyl (wherein the ring of said benzyl or phenyl group is not halogen, cyano, nitro, or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, the ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R 4 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, (CH2CH2O)tR 5or benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, wherein the ring is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R 5 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or benzyl or phenyl (wherein the ring in the benzyl or phenyl group is not halogen, cyano, or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, the ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; t is an integer from 1 to 10; X is a direct bond, O, S or NR 6 and; R6 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or benzyl or phenyl (wherein the ring in the benzyl or phenyl group is not halogen, cyano, nitro) or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, the ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; or R 4 and R 6 can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing carbon atoms and optionally 1-3 oxygen, sulfur, or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and sulfur atom ring members are selected from S, S(O), or S(O)2, and the ring is optionally substituted with at least one substituent independently selected from the group consisting of C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; A is, [ka] is selected from X 1 , X 2 , X3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 are each independently N or CR 7 where X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 of which no more than four are N; X 11 is O, S or NR 9 or X 11 is -C(R 10 )=C(R 11 )-, and in formula 1, R 10 The carbon atom bonded to R 13 It is also bonded to the carbon atom bonded to R 11 The carbon atom bonded to is also bonded to a phenyl ring moiety; Y is O, S or NR 8 and; Y 1 O, S, NR 8 or CR 7a R 7b and; Each R 7 are independently H, halogen, cyano, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R 7ais H, halogen, —CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R 7b is H, halogen, —CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; or R 7a and R 7b is combined with =O or R 7a and R 7b together with the carbon atoms to which they are attached form an optionally substituted 3- to 7-membered carbocyclic ring; R 8 is H, C1-C3 alkyl or C1-C3 haloalkyl; R 9 is H, C1-C3 alkyl or C1-C3 haloalkyl; R 10 and R 11are independently H, halogen, nitro, -CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; Each R 12 are independently halogen, —CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R 13 is H, halogen, nitro, -CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R 14 is H; n is 0, 1, 2, 3 or 4.

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

[0005] The present invention also includes herbicidal mixtures comprising: (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1)-(b16); and salts of compounds (b1)-(b16) (described below). DETAILED DESCRIPTION OF THE INVENTION

[0006] As used herein, the terms "comprises," "comprising," "includes," "including," "contains," "containing," "has," "having," "characterized by," or any variation thereof, are intended to include a non-exclusive inclusion, subject to any limitations expressly indicated. For example, a composition, mixture, process, or method that includes a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent in such composition, mixture, process, or method.

[0007] The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. In claims, when a claim is closed to encompass substances different from those recited, apart from impurities, it is usually relevant. When the phrase "consisting of" appears in a clause in the body of a claim rather than immediately following the preamble, it limits only the elements recited in that clause; other elements are not excluded from the claim as a whole.

[0008] The transitional phrase "consisting essentially of" is used to define compositions or methods that include materials, steps, structures, ingredients, or elements in addition to those literally disclosed, provided that these additional materials, steps, structures, ingredients, or elements do not materially affect the basic and novel characteristics of the claimed invention.

[0009] The term "consisting essentially of" occupies a middle ground between "comprising" and "consisting of."

[0010] It should be readily understood that where applicants have defined the invention or any portion thereof with open-ended terms such as "comprising," the statement should be construed as also describing such inventions using the terms "consisting essentially of" or "consisting of" (unless otherwise stated).

[0011] Furthermore, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or." For example, the condition "A or B" is satisfied by any one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0012] Furthermore, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be open-ended regarding the number of instances (i.e., occurrences) of that element or component. Thus, "a" and "an" should be read to include one or at least one, and such singular word forms of that element or component also include the plural, unless it is clear that the number refers to the singular.

[0013] As referred to herein, the term "seedling", used alone or in combination, means a young plant developing from the germ of a seed.

[0014] As referred to herein, the term "broadleaf," used alone or in terms such as "broadleaf weed," means a dicot or dicotyledon, a term used to describe a group of angiosperms characterized by an embryo with two cotyledons.

[0015] As used herein, the term "alkylation" refers to a reaction in which a nucleophile displaces a leaving group, such as a halide or sulfonate, from a carbon-containing radical. Unless otherwise indicated, the term "alkylation" does not limit the carbon-containing radical to alkyl.

[0016] In the above description, the term "alkyl," used alone or in compound terms such as "alkylthio" or "haloalkyl," includes straight-chain or branched alkyls, such as methyl, ethyl, n-propyl, i-propyl, or the various butyl, pentyl, or hexyl isomers. "Alkenyl" includes straight-chain or branched alkenes, such as ethenyl, 1-propenyl, 2-propenyl, and the various butenyl, pentenyl, and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl, and the various butynyl, pentynyl, and hexynyl isomers. "Alkynyl" can also include moieties consisting of multiple triple bonds, such as 2,5-hexadiynyl.

[0017] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, and the various butoxy, pentoxy, and hexyloxy isomers. "Alkoxyalkyl" indicates alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CHOCH, CHOCHCH, CHCHOCH, CHCHCHCHOCH, and CHCHOCHCH. "Alkoxyalkoxy" indicates alkoxy substitution with alkoxy. "Alkylthio" includes branched or straight-chain alkylthio residues, such as methylthio, ethylthio, and the various propylthio, butylthio, pentylthio, and hexylthio isomers. "Alkylthioalkyl" indicates alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CHSCH, CHSCHCH, CHCHSCH, CHCHCHCHSCH, and CHCHSCHCH. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S(O)-, CH3CH2S(O)-, CH3CH2CH2S(O)-, (CH3)2CHS(O)-, and the various butylsulfinyl, pentylsulfinyl, and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and the various butylsulfonyl, pentylsulfonyl, and hexylsulfonyl isomers. "Cyanoalkyl" refers to an alkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH2 and NCCH2CH2 (alternatively identified as CH2CH2CN). "Nitroalkyl" refers to an alkyl group substituted with one nitro group. Examples of "nitroalkyl" include NO2NCH2 and NO2NCH2CH2 (alternatively identified as CH2CH2NO2). "Cyano" means NC-- and "formyl" means HC(=O)--. "Alkylamino" includes an NH radical substituted with a straight-chain or branched alkyl.Examples of "alkylamino" include CH3CH2NH, CH3CH2CH2NH, and (CH3)2CHCH2NH. Examples of "dialkylamino" include (CH3)2N, (CH3CH2CH2)2N, and CH3CH2(CH3)N.

[0018] "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "cycloalkylalkyl" denotes cycloalkyl substitution on an alkyl moiety. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl residues bonded to straight-chain or branched alkyl groups. The term "alkylcycloalkyl" refers to an alkyl group bonded to a cycloalkyl moiety.

[0019] The term "halogen," when used alone or in compound terms such as "haloalkyl" or in descriptions such as "alkyl substituted with halogen," includes fluorine, chlorine, bromine, or iodine. Furthermore, when used in compound terms such as "haloalkyl" or in descriptions such as "alkyl substituted with halogen," the alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of "haloalkyl" or "alkyl substituted with halogen" include F3C, ClCH2, CF3CH2, and CFC12. Terms such as "haloalkoxy," "haloalkoxyalkyl," "haloalkylthio," "haloalkenyl," and "haloalkynyl" are as defined analogously to the term "haloalkyl." Examples of "haloalkoxy" include CFO-, CCl3CHO-, HCF2CH2CHO-, and CF3CHO-. Examples of "haloalkoxyalkyl" include CF3OCH2-, CCl3CHOCH2-, HCF2CH2CH2OCH2-, and CF3CHOCH2-. Examples of "haloalkylthio" include CCl3S-, CF3S-, CCl3CH2S-, and ClCH2CH2CH2S-. Examples of "haloalkenyl" include (Cl)2C=CHCH2-, and CF3CH2CH=CHCH2-. Examples of "haloalkynyl" include HC≡CCHCl-, CF3C≡C-, CCl3C≡C-, and FCH2C≡CCH2-.

[0020] "Alkylcarbonyl" refers to a straight-chain or branched alkyl moiety attached to a C(=O) moiety. Examples of "alkylcarbonyl" include CHC(=O)-, CHCHC(=O)-, CHCHCHC(=O)-, (CH)CHC(=O)-, and the different butoxy- or pentoxycarbonyl isomers. "Alkoxycarbonyl" refers to a straight-chain or branched alkoxy moiety attached to a C(=O) moiety. Examples of "alkoxycarbonyl" include CHOC(=O)-, CHCHOC(=O)-, CHCHCHOC(=O)-, (CH)CHOC(=O)-, and the different butoxy- or pentoxycarbonyl isomers. C(=O) or C(O) represents a carbonyl. The term "alkoxycarbonylalkyl" refers to a straight-chain or branched alkoxycarbonyl moiety attached via an alkyl moiety. The term "alkylcarbonylalkyl" refers to a straight-chain or branched alkylcarbonyl moiety attached via an alkyl moiety. The term "alkylcarbonyloxy" refers to an alkylcarbonyl moiety attached via an oxygen. Examples of alkylcarbonyloxy include CHC(=O)O-, CHCHC(=O)O-, CHCHCHC(=O)O-, and (CH)CHC(=O)-. The terms alkanediyl or alkenediyl refer to straight-chain or branched alkane or alkene linkage chains, respectively. Examples of alkanediyl include -CH-, -CHCH(CH)-, or -CHCHCH-. Examples of alkenediyl include -CH=CH-, -CHC=CH-, or -CH=C(CH)-. The term "adjacent," in the context of placing a substituent, means "next to" or "immediately adjacent."

[0021] The total number of carbon atoms in a substituent is indicated by the prefix "Ci-Cj," where i and j are numbers from 1 to 8. For example, C1-C4 alkylsulfonyl refers to methylsulfonyl through butylsulfonyl, C3-C8 alkylcarbonylalkyl refers to, for example, CH3COCH2-, CH3COCH2CH2-, or CH3CH2CH2COCH2CH2CH2-; C4-C7 alkylcycloalkyl can be, for example, methylcyclopropyl, methylcyclobutyl, ethylcyclopropyl, or propylcyclobutyl; C2 alkoxyalkyl refers to CHOCH2-; C3 alkoxyalkyl refers to, for example, CH3CH(OCH3)-, C3OCH2CH2-, or CH3CHOCH2-; and C4 alkoxyalkyl refers to the various isomers of an alkyl group substituted with an alkoxy group containing a total of 4 carbon atoms, such as CH3CH2CHOCH2- and CH3CHOCH2CH2-.

[0022] A group may have a substituent that can be hydrogen, such as (R 3 or Rv) and then this substituent is hydrogen, this is considered equivalent to saying that the group is unsubstituted. When one or more positions on a group are described as "unsubstituted" or "unsubstituted," a hydrogen atom is bonded to occupy any free valence. Unless specifically indicated as optionally substituted, the term "phenyl" means unsubstituted phenyl. Unless specifically indicated as optionally substituted, the term "benzyl" means unsubstituted benzyl.

[0023] When a compound is substituted with a substituent bearing a subscript indicating that the number of substituents can be more than one, the substituents (if there are more than one) can be independently selected from a defined group of substituents, e.g., ([(R 12)n], where n is selected from 0, 1, 2, 3, or 4). When n is 0, a hydrogen can be at that position even if it is not listed in the definition of the substituent. When a functional group or compound is indicated as optionally substituted with a substituent, the functional group or compound can be unsubstituted or substituted. When one or more positions on a group are described as "unsubstituted" or "unsubstituted," a hydrogen atom is bonded to occupy any free valence.

[0024] If A is A-11, (R 12 )n attachment points are shown as floating. 12 can be attached to any of the five available aromatic carbons by substitution of a hydrogen atom.

[0025] The term "ring system" means two or more fused rings. The term "bicyclic ring system" means a ring system consisting of two fused rings.

[0026] The compounds of the present invention may exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. Stereoisomers are isomers that have identical constitution but differ in the spatial arrangement of their atoms, including enantiomers, diastereomers, cis-trans isomers (also called geometric isomers), and atropisomers. Atropisomers result from restricted rotation around a single bond, and the high barrier to rotation allows for the isolation of these isomeric species. As will be appreciated by those skilled in the art, one stereoisomer may be more reactive and / or exhibit advantageous effects when enriched or separated from other stereoisomers. Additionally, those skilled in the art know methods for separating, enriching, and / or selectively preparing stereoisomers. The compounds of the present invention can exist as a mixture of stereoisomers, as individual stereoisomers, or as optically active forms.

[0027] Compounds of Formula 1 typically exist in more than one form, and therefore Formula 1 encompasses all crystalline and amorphous forms of the compounds represented therein. Amorphous forms include solid embodiments, such as waxes and rubbers, as well as liquid embodiments, such as solutions and melts. Crystalline forms include embodiments that represent a substantially single crystal type and embodiments that represent a mixture of polymorphs (i.e., multiple crystalline types). The term "polymorph" refers to a specific crystalline form of a compound that can crystallize in various crystalline forms, which have different molecular arrangements and / or conformations in the crystal lattice. Multiple polymorphs can have the same chemical composition, but they can also differ in composition due to the presence or absence of co-crystallized water or other molecules that may be weakly or strongly bound in the lattice. Polymorphs can differ in chemical, physical, and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate, and biological availability.

[0028] As will be appreciated by those skilled in the art, polymorphs of the compound of Formula 1 may exhibit advantageous effects (e.g., suitability in preparing useful formulations, improved biological performance) compared to other polymorphs or mixtures of polymorphs of the same compound of Formula 1. The preparation and isolation of a particular polymorph of the compound of Formula 1 can be achieved by methods known to those skilled in the art, such as, for example, 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. Those skilled in the art will understand that not all nitrogen-containing heterocycles can form N-oxides because the nitrogen requires an available lone pair of electrons to be oxidized to the oxide. Those skilled in the art will recognize those 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 will be well known to those skilled in the art, including the oxidation of heterocycles and tertiary amines using peroxyacids such as peracetic acid and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for preparing N-oxides have been widely described and reviewed in the literature, see for example the following references: T. L. Gilchrist, Comprehensive Organic Synthesis, vol. 7, pp. 748-750 (S.V. Ley, Ed., Pergamon Press); M. Tisler and B. Stanovnik, Comprehensive Heterocyclic Chemistry, vol. 3, pp. 18-20, A.J. Boulton and A. McKillop, Eds., Pergamon Press; M.R. Grimmett and B.R.T. Keene, Advances in Heterocyclic Chemistry, vol. 43, pp. 149-161, A.R.Katrittzky, Eds., Academic Press; M. Tisler and B. Stanovnik, Advances in Heterocyclic Chemistry, vol. 9, pp. 285-291, A.R.Katrittzky and A.J.Boulton, Eds., Academic Press Press; and GWHCheeseman and ESGWerstiuk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, ARKatritzky and AJ Boulton, Eds., Academic Press.

[0029] Those skilled in the art will recognize that salts of compounds share biological utility with their corresponding non-salt forms because, under environmental and physiological conditions, salts are in equilibrium with their corresponding non-salt forms. Thus, a wide variety of salts of compounds of Formula 1 are useful for controlling undesirable vegetation (i.e., suitable as pesticides). Salts of compounds of Formula 1 include, for example, acid addition salts with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propynoic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. When compounds of Formula 1 contain acidic residues, salts also include those formed with organic or inorganic bases, such as pyridine, triethylamine, or ammonia, or amides, hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium, or barium. Thus, the present invention includes compounds selected from Formula 1, their N-oxides and pesticide-suitable salts.

[0030] R 1 , R 3 , R 4 , R 5 , or R 6 When R is a 5- or 6-membered nitrogen-containing heterocycle, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom, unless otherwise specified. 1 , R 2 , R 3 , R 4 , R 5 , or R 6 can be phenyl optionally substituted with one or more substituents selected from the group of substituents defined in the Summary of the Invention (i.e., halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy) (among others). An example of a phenyl optionally substituted with 1 to 5 substituents is the ring shown as U-1 in Exhibit 1, where R is any of the R groups defined in the Summary of the Invention.5 , R 6 or R 7 where r is an integer.

[0031] As mentioned above, R 1 , R 3 , R 4 , R 5 , or R 6 can be (among other things) a 5- or 6-membered heterocyclic ring which may be saturated or unsaturated and optionally substituted with one or more substituents selected from the group of substituents defined in the Summary of the Invention. Examples of 5- or 6-membered unsaturated aromatic heterocyclic rings which may be substituted with one or more substituents include rings U-2 through U-61 shown in Exhibit 1, where R is independently halogen, C1-C4 alkyl, or C1-C4 haloalkyl, and r is an integer from 0 to 4, limited by the number of available positions for each U group. U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42, and U-43 have only one available position, and for these U groups, r is limited to the integer 0 or 1, where r being 0 means that the U group is unsubstituted and a hydrogen is present at the position indicated by (R)r. [ka] [ka] [ka]

[0032] R 1 , R 3 , R 4 , R 5 or R 6 But R 1 , R 3 , R 4 , R 5 or R 6It should be noted that when the heterocyclic ring is a 5- or 6-membered saturated or unsaturated non-aromatic heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents defined in the Summary of the Invention for, one or two carbon ring members of the heterocyclic ring may optionally be in the oxidized form of a carbonyl moiety.

[0033] Examples of 5- or 6-membered heterocyclic rings that are saturated or non-aromatic unsaturated heterocyclic rings containing ring members selected from up to two O atoms and up to two S atoms, and optionally substituted on carbon atom ring members with up to four Rv, include rings T-1 to T-35 as shown in Exhibit 2. Note that when the attachment point on the T group is shown as floating, the T group can be bonded to the remainder of Formula 1 through any available carbon or nitrogen of the T group by replacing a hydrogen atom. Optional substituents corresponding to Rv can be bonded to any available carbon or nitrogen by replacing a hydrogen atom. For these T rings, r is typically an integer from 0 to 4, limited by the number of available positions on each T group. The term "optionally substituted" means "substituted or unsubstituted." T 2 is N, the nitrogen atom is R 5 , R 6 or R 7 Note that the valency can be completed by substitution with either H or a substituent corresponding to R, as defined in the Summary of the Invention above. 1 Exemplary values ​​of T include T-1, T-2, T-7, and T-9 (i.e., R 1 is a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and at most one ring member selected from O and at most one ring member selected from S), as well as T-28 to T-31, 2 is O or S. [ka] [ka]

[0034] Note that while R groups are shown in structures U-1 through U-61, they are optional substituents and therefore do not need to be present. Note that if R is H when attached to an atom, this is the same as if that atom were unsubstituted. Nitrogen atoms that require substitution to satisfy valence are substituted with H or R. Note that if the point of attachment between (R)r and the U group is shown as floating, then (R)r can be attached to any available carbon or nitrogen atom of the U group. Note that if the point of attachment on the U group is shown as floating, then the U group can be attached to the remainder of Formula 1 through any available carbon or nitrogen atom of the U group by replacement of a hydrogen atom. Note that some U groups can be substituted with fewer than four R groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 through U-61).

[0035] A wide variety of synthetic methods are known in the art that allow the preparation of aromatic and non-aromatic heterocyclic rings and ring structures. For detailed reviews, see the eight-volume set Comprehensive Heterocyclic Chemistry (A.R. Katrittzky and C.W. Rees, editors-in-chief, Pergamon Press, Oxford, 1984) and the twelve-volume set Comprehensive Heterocyclic Chemistry II (A.R. Katrittzky, C.W. Rees, and E.F.V. Scriven, editors-in-chief, Pergamon Press, Oxford, 1996).

[0036] Embodiments of the 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, and references to "compounds of Formula 1" include the definitions of the substituents defined in the Summary of the Invention, unless further defined in the embodiments.

[0037] Embodiment 1. Compounds of Formula 1 as described in the Summary of the Invention, their stereoisomers, N-oxides and salts, agricultural compositions containing them and their use as herbicides.

[0038] Embodiment 2a. The compound of embodiment 1, wherein A is A-11.

[0039] Embodiment 2b. The compound of embodiment 1, wherein A is A-1.

[0040] Embodiment 2c. The compound of embodiment 1, wherein A is A-2.

[0041] Embodiment 2d. The compound of embodiment 1, wherein A is A-3.

[0042] Embodiment 2e. The compound of embodiment 1, wherein A is A-4.

[0043] Embodiment 2f. The compound of embodiment 1, wherein A is A-5.

[0044] Embodiment 2g. The compound of embodiment 1, wherein A is A-6.

[0045] Embodiment 2h. The compound of embodiment 1, wherein A is A-7.

[0046] Embodiment 2i. The compound of embodiment 1, wherein A is A-8.

[0047] Embodiment 2j. The compound of embodiment 1, wherein A is A-9.

[0048] Embodiment 2k. The compound of embodiment 1, wherein A is A-10.

[0049] Embodiment 21. A compound according to embodiment 1, wherein A is selected from A-1, A-4 and A-6.

[0050] Embodiment 2m. A compound according to embodiment 1, wherein A is selected from A-9 and A-10.

[0051] Embodiment 3a.R 1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0052] Embodiment 3b.R 1 is C1-C7 alkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, or benzyl substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0053] Embodiment 3c.R 1Compounds according to embodiment 3b, wherein is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl, C2-C3 cyanoalkyl, C1-C3 haloalkyl, or C2-C4 alkoxyalkyl.

[0054] Embodiment 3d.R 1 Compounds according to embodiment 3c, wherein is C1-C3 alkyl, allyl, propargyl, CH2CH2CN, C1-C2 haloalkyl, or 2-methoxyethyl.

[0055] Embodiment 3e.R 1 Compounds according to embodiment 3d, wherein is methyl, ethyl, n-propyl, or 2-methoxyethyl.

[0056] Embodiment 3f.R 1 A compound according to embodiment 3e, wherein is methyl or ethyl.

[0057] Embodiment 3g.R 1 The compound according to embodiment 3f, wherein is methyl.

[0058] Embodiment 3h.R 1 The compound of embodiment 3a or 3b, wherein is other than H.

[0059] Embodiment 3i.R 1 The compound of embodiment 3a, wherein is other than phenyl.

[0060] Embodiment 4a.R 2is H, halogen, cyano, formyl, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, or C2-C3 alkoxycarbonyl.

[0061] Embodiment 4b.R 2 Compounds according to embodiment 4a, wherein is H, halogen, —CN, —CHO, C1-C7 alkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, or C1-C7 alkoxy.

[0062] Embodiment 4c.R 2 Compounds according to embodiment 4b, wherein is H, halogen, —CN, C1-C4 alkyl, C3-C5 cycloalkyl, C1-C3 haloalkyl, C2-C4 alkoxyalkyl, or C1-C3 alkoxy.

[0063] Embodiment 4d.R 2 Compounds according to embodiment 4c, wherein is H, halogen, C1-C3 alkyl, cyclopropyl, C1-C2 haloalkyl, methoxy, or ethoxy.

[0064] Embodiment 4e.R 2 Compounds according to embodiment 4d, wherein is H, F, Cl, Br, methyl, ethyl, n-propyl, CF3, or methoxy.

[0065] Embodiment 4f.R 2 A compound according to embodiment 4e, wherein is methyl or ethyl.

[0066] Embodiment 4g.R 2 The compound according to embodiment 4f, wherein is methyl.

[0067] Embodiment 4h.R 2 Compounds according to embodiment 4e, wherein is F or Cl.

[0068] Embodiment 4i.R 2 The compound of embodiment 4h, wherein is F.

[0069] Embodiment 4h.R 2 The compound of embodiment 4h, wherein is Cl.

[0070] Embodiment 4i.R 2 Compounds according to embodiment 4e, wherein is Me or Cl.

[0071] Embodiment 4j.R 2 is other than phenyl.

[0072] Embodiment 4j.R 2 is other than H.

[0073] Embodiment 5a.R 3is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0074] Embodiment 5b.R 3 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, or C1-C7 alkoxy.

[0075] Embodiment 5c.R 3 Compounds according to embodiment 5b, wherein is H, C1-C4 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, or C1-C7 alkoxy.

[0076] Embodiment 5d.R3 Compounds according to embodiment 5c, wherein is H, C1-C4 alkyl, C4-C7 alkylcycloalkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, or C1-C7 alkoxy.

[0077] Embodiment 5e.R 3 Compounds according to embodiment 5d, wherein is H, C1-C4 alkyl, C3-C7 haloalkyl, C4-C7 cycloalkyl, or C1-C7 alkoxy.

[0078] Embodiment 5f.R 3 Compounds according to embodiment 5e, wherein is H, methyl, ethyl, cyclopropyl, cyclopropylmethyl, or methoxy.

[0079] Embodiment 5g.R 3 Compounds according to embodiment 5f, wherein is H, methyl, ethyl, cyclopropyl, or cyclopropylmethyl.

[0080] Embodiment 5h.R 3 The compound of embodiment 5g, wherein is H or methyl.

[0081] Embodiment 5i.R 3 The compound of embodiment 5h, wherein

[0082] Embodiment 5j.R 3 is benzyl.

[0083] Embodiment 6a. The compound of any of the preceding embodiments, wherein X is a direct bond.

[0084] Embodiment 6b. A compound according to embodiments 1-5, wherein X is O.

[0085] Embodiment 6c. The compound of any one of embodiments 1-5, wherein X is S.

[0086] Embodiment 6d.X is NR 6 6. The compound of embodiments 1-5, wherein:

[0087] Embodiment 6e. A compound according to any one of embodiments 1-5, wherein X is a direct bond or O.

[0088] Embodiment 7a.R 4 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, (CH2CH2O)tR 5 or benzyl or phenyl, wherein a ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0089] Embodiment 7b.R 4 is a 5- or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to one O and up to one S, wherein the ring is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0090] Embodiment 7c.R 4Compounds according to embodiment 7a, wherein is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, or C1-C7 alkoxy.

[0091] Embodiment 7d.R 4 Compounds according to embodiment 7c, wherein is H, C1-C4 alkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, or C1-C7 alkoxy.

[0092] Embodiment 7e.R 4 Compounds according to embodiment 7d, wherein is H, C1-C4 alkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, or C1-C7 alkoxy.

[0093] Embodiment 7f.R 4 Compounds according to embodiment 7e, wherein is C1-C4 alkyl, C4-C7 cycloalkylalkyl, or C1-C7 alkoxy.

[0094] Embodiment 7g.R 4 Compounds according to embodiment 7f, wherein is H, methyl, ethyl, i-propyl, t-Bu, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, or ethoxy.

[0095] Embodiment 7h.R 4 Compounds according to embodiment 7f, wherein is H, methyl, ethyl, i-propyl, t-Bu, or methoxy. Embodiment 8a.R 5is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl; or is benzyl or phenyl, wherein a ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0096] Embodiment 8b.R 5 The compound of embodiment 8a, wherein is C1-C7 alkyl.

[0097] Embodiment 8c.R 5 The compound of embodiment 8a, wherein

[0098] Embodiment 8d.R 5 The compound of embodiment 8a, wherein is C3-C8 alkylcarbonylalkyl.

[0099] Embodiment 8e.R 5 is benzyl optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0100] Embodiment 9a.R 6is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or benzyl or phenyl (the ring in said benzyl or phenyl group is not halogen, cyano, nitro, C1-C4 alkoxy). or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, said ring optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0101] Embodiment 9b.R 6is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0102] Embodiment 9c.R 6 Compounds according to embodiment 9b, wherein is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, or C1-C7 alkoxy.

[0103] Embodiment 9d.R 6 Compounds according to embodiment 9c, wherein is H or C1-C7 alkyl.

[0104] Embodiment 9e.R 6 The compound of embodiment 9c, wherein is C1-C3 alkyl.

[0105] Embodiment 9f.R 6 The compound of embodiment 9e, wherein is Me.

[0106] Embodiment 9g.R 4 and R 6can be taken together with the nitrogen atom to which they are attached to form a 3-7 membered ring containing carbon atoms and optionally 1-3 oxygen, sulfur, or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O), or S(O)2, and the ring is unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy.

[0107] Embodiment 9h.R 4 and R 6 Compounds according to embodiment 9g, wherein can be taken together with the nitrogen atom to form a three-membered ring.

[0108] Embodiment 9i.R 4 and R 6 Compounds according to embodiment 9g, wherein can be taken together with the nitrogen atom to form a four-membered ring.

[0109] Embodiment 9j.R 4 and R 6 Compounds according to embodiment 9g, wherein can be taken together with the nitrogen atom to form a five-membered ring.

[0110] Embodiment 9k.R 4 and R 6 Compounds according to embodiment 9g, wherein can be taken together with the nitrogen atom to form a six-membered ring.

[0111] Embodiment 9l.R 4 and R 6 can be taken together with the nitrogen atom to which they are attached to form pyrrolidine, piperidine, or piperazine.

[0112] Embodiment 10a.X 1 , X 2 , X 3 , X 4, X 5 , X 6 , X 7 , X 8 , X 9 and X 10 Each of these is CR 7 The compound of any one of the preceding embodiments, wherein

[0113] Embodiment 10b. A is A-1 and each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 and X 9 A compound according to Formula 1 or any one of the preceding embodiments, wherein is CH.

[0114] Embodiment 11a. Each R 7 The compound of any one of the preceding embodiments, wherein is independently H, halogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, or C1-C3 alkoxy.

[0115] Embodiment 11b. Each R 7 Compounds according to embodiment 11a, wherein is independently H, halogen, C1-C2 alkyl, cyclopropyl, or C1-C2 haloalkyl.

[0116] Embodiment 11c. Each R 7 Compounds according to embodiment 11b, wherein is independently H, halogen, methyl, ethyl, or CF3.

[0117] Embodiment 11d. Each R 7 Compounds according to embodiment 11c, wherein is independently H, F, Cl, Br, or methyl.

[0118] Embodiment 11e. Each R 7 The compound of embodiment 11d, wherein

[0119] Embodiment 11f. Each R 7The compound of embodiment 11d, wherein is Me.

[0120] Embodiment 11g. Each R 7 The compound of embodiment 11d, wherein is F.

[0121] Embodiment 11h. Each R 7 The compound of embodiment 11d, wherein is Cl.

[0122] Embodiment 12. X 11 is O, S or NR 9 or X 11 But -C(R 10 )=C(R 11 )-.

[0123] Embodiment 12a.X 11 is O, S or NR 9 The compound of any of the preceding embodiments, wherein

[0124] Embodiment 12b.X 11 The compound of embodiment 12a, wherein

[0125] Embodiment 12c.X 11 The compound of embodiment 12a, wherein is S.

[0126] Embodiment 12d.X 11 NR 9 The compound of embodiment 12a, wherein

[0127] Embodiment 12e.X 11 -C(R 10 )=C(R 11 )-.

[0128] Embodiment 12f.X 11 The compound of any of embodiments 1 to 11h, wherein is O, S, —CH═CH—, —C(CH3)═CH—, —CH═CF—, —CH═CCl—, or —CH═C(CH3)—.

[0129] Embodiment 12g.X 11 Compounds according to embodiment 12f, wherein is -CH=CH-, -C(CH3)=CH-, -CH=CF-, -CH=CCl-, or -CH=C(CH3)-.

[0130] Embodiment 12h.X 11 Compounds according to embodiment 12g, wherein is -CH=CH-, -CH=CF-, -CH=CCl-, or -CH=C(CH3)-.

[0131] Embodiment 12i. X 11 The compound of embodiment 12h, wherein is -CH=CH-.

[0132] Embodiment 13a.R 9 The compound of any one of the preceding embodiments, wherein is C1-C2 alkyl.

[0133] Embodiment 13b.R 9 is methyl.

[0134] Embodiment 14a. Independently, R 10 and R 11

[0023] The compound of any one of the preceding embodiments, wherein is H, halogen, -CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio, or C1-C2 haloalkylthio.

[0135] Embodiment 14b.R 10 and R 11 Compounds according to embodiment 14a, wherein is independently H, halogen, -CN, C1-C2 alkyl, -CH=CH2, -C≡CH, cyclopropyl, C1-C2 haloalkyl, or C1-C2 alkoxy.

[0136] Embodiment 14c.R 10 and R 11Compounds according to embodiment 14b, wherein is independently H, halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy, or ethoxy.

[0137] Embodiment 14d.R 10 and R 11 Compounds according to embodiment 14c, wherein is independently H, halogen, or C1-C2 alkyl.

[0138] Embodiment 14e.R 10 and R 11 Compounds according to embodiment 14d, wherein is independently H or halogen.

[0139] Embodiment 14f.R 10 is H and R 11 The compound of embodiment 14d, wherein is halogen.

[0140] Embodiment 14g.R 10 is a halogen and R 11 The compound of embodiment 14d, wherein

[0141] Embodiment 14h.R 10 and R 11 Compounds according to embodiment 14c, wherein is independently H or C1-C2 alkyl.

[0142] Embodiment 14i.R 10 The compound of embodiment 14g, wherein is H or methyl (ie, CH3).

[0143] Embodiment 14j.R 10 is H and R 11 is H or R 10 is H and R 11 is CH3 or R 10 is CH3 and R 11 The compound of embodiment 14h, wherein

[0144] Embodiment 14k.R 10 is H and R 11The compound of embodiment 14i, wherein

[0145] Embodiment 15a. Each R 12 are independently halogen, —CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio, or C1-C2 haloalkylthio.

[0146] Embodiment 15b. Each R 12 Compounds according to embodiment 15a, wherein is independently halogen, -CN, C1-C2 alkyl, -CH=CH2, -C≡CH, cyclopropyl, C1-C2 haloalkyl, or C1-C2 alkoxy.

[0147] Embodiment 15c. Each R 12 Compounds according to embodiment 15b, wherein is independently halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy, or ethoxy.

[0148] Embodiment 15d. Each R 12 Compounds according to embodiment 15c, wherein is independently halogen, —CN, methyl, ethyl, methoxy, or ethoxy.

[0149] Embodiment 15e. Each R 12 Compounds according to embodiment 15d, wherein is independently F, Cl, Br, methyl, ethyl, or methoxy.

[0150] Embodiment 15f. Each R 12 The compound of embodiment 15e, wherein is methyl.

[0151] Embodiment 15g. Each R 12 The compound of embodiment 15e, wherein is F.

[0152] Embodiment 15h. Each R 12 The compound of embodiment 15e, wherein is Cl.

[0153] Embodiment 16a.R 13 is H, halogen, —CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio, or C1-C2 haloalkylthio.

[0154] Embodiment 16b.R 13 Compounds according to embodiment 16a, wherein is halogen, -CN, C1-C2 alkyl, -CH=CH2, -C≡CH, cyclopropyl, C1-C2 haloalkyl, or C1-C2 alkoxy.

[0155] Embodiment 16c.R 13 Compounds according to embodiment 16b, wherein is halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy, or ethoxy.

[0156] Embodiment 16d.R 13 A compound according to embodiment 16c, wherein is Me or ethyl.

[0157] Embodiment 16e.R 13 Compounds according to embodiment 16d, wherein is Me or Cl.

[0158] Embodiment 16f.R 13 The compound of embodiment 16e, wherein is Me.

[0159] Embodiment 16g.R 13 The compound of embodiment 16e, wherein is Cl.

[0160] Embodiment 16h.R 13 The compound of embodiment 16e, wherein is F.

[0161] Embodiment 17. A compound according to Formula 1 or any one of the preceding embodiments, wherein n is 0, 1, 2, 3 or 4.

[0162] Embodiment 17a. A compound according to embodiment 17, wherein n is 0, 1 or 2.

[0163] Embodiment 17A compound according to embodiment 17, wherein aa.n is 1 or 2.

[0164] Embodiment 17b. A compound according to embodiment 17a, wherein n is 0.

[0165] Embodiment 17c. A compound according to embodiment 17a, wherein n is 1.

[0166] Embodiment 17d. A compound according to embodiment 17a, wherein n is 2.

[0167] Embodiments of the invention, including embodiments 1-17d above and any other embodiments described herein, can be combined in any manner, and the descriptions of the variables in the embodiments relate not only to compounds of Formula 1, but also to starting compounds and intermediate compounds useful for preparing compounds of Formula 1. Additionally, embodiments of the invention, including embodiments 1-17d above and any other embodiments described herein, and any combination thereof, relate to compositions and methods of the invention.

[0168] Combinations of embodiments 1 to 17d are shown below.

[0169] Embodiment A. A compound of Formula 1 as described in the Summary of the Invention, A is A-11; R 1is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or is benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R 2 is H, halogen, cyano, formyl, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio or C2-C3 alkoxycarbonyl; R 3is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or is benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R 4 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, -C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, (CH2CH2O)tR 5 or benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; Each R 12 are independently halogen, —CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio, or C1-C2 haloalkylthio; R13 is halogen, —CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio or C1-C2 haloalkylthio; A compound of Formula 1 as described in the Summary of the Invention.

[0170] Embodiment A1. A compound according to embodiment A, R 1 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl, C2-C3 cyanoalkyl, C1-C3 haloalkyl or C2-C4 alkoxyalkyl; R 2 is H, halogen, —CN, C1-C4 alkyl, C3-C5 cycloalkyl, C1-C3 haloalkyl, C2-C4 alkoxyalkyl or C1-C3 alkoxy; R 3 is H, C1-C4 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl or C1-C7 alkoxy; R 4 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl or C1-C7 alkoxy; R 12 is independently halogen, —CN, methyl, ethyl, methoxy, or ethoxy; R 13 is halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy; A compound according to embodiment A.

[0171] Embodiment A2. A compound according to embodiment A1, R 1 is C1-C3 alkyl, allyl, propargyl, CH2CH2CN, C1-C2 haloalkyl, or 2-methoxyethyl; R 2 is H, halogen, C1-C3 alkyl, cyclopropyl, C1-C2 haloalkyl, methoxy or ethoxy; R 3 is H, C1-C4 alkyl, C3-C7 haloalkyl, C4-C7 cycloalkyl, or C1-C7 alkoxy; R 4 is H, C1-C4 alkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl or C1-C7 alkoxy; Each R 12 is independently F, Cl, Br, methyl, ethyl, or methoxy; n is 0, 1 or 2; A compound according to embodiment A1.

[0172] Embodiment A3. A compound according to embodiment A2, R 1 is methyl, ethyl, n-propyl or 2-methoxyethyl; R 2 is H, F, Cl, methyl, ethyl, n-propyl, CF3 or methoxy; R 3 is H or methyl; R 4 is H, C1-C4 alkyl, C4-C7 cycloalkylalkyl or C1-C7 alkoxy; X 11 But -C(R 10 )=C(R 11 )- and Independently, R 10 and R 11 is H, halogen or C1-C2 alkyl; A compound according to embodiment A2.

[0173] Embodiment A4. A compound according to embodiment A3, R 1 is methyl; R 2 is Me or Cl; R 3 is H; R 4 is H, methyl, ethyl, i-propyl, t-Bu, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy or ethoxy; R 10 is H and R 11 is H or R 10 is H and R 11 is CH3 or R 10 is CH3 and R 11 is H, A compound according to embodiment A3.

[0174] Embodiment A5. A compound according to embodiment A2, R 1 is methyl, ethyl, n-propyl or 2-methoxyethyl; R 2 is H, F, Cl, methyl, ethyl, n-propyl, CF3 or methoxy; R 3 is H or methyl; R 4 is H, C1-C4 alkyl, C4-C7 cycloalkylalkyl or C1-C7 alkoxy; X 11 is O, A compound according to embodiment A2.

[0175] Embodiment A6. A compound according to embodiment A2, R 1 is methyl, ethyl, n-propyl or 2-methoxyethyl; R 2 is H, F, Cl, methyl, ethyl, n-propyl, CF3 or methoxy; R 3 is H or methyl; R 4 is H, C1-C4 alkyl, C4-C7 cycloalkylalkyl or C1-C7 alkoxy; X 11 is S, A compound according to embodiment A2.

[0176] Embodiment A7. A compound according to embodiment A2, X is a direct bond or O; A compound according to embodiment A2.

[0177] Embodiment B. A compound of Formula 1 as described in the Summary of the Invention, A is selected from A-1, A-4 and A-6; R 1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or is benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R 2is H, halogen, cyano, formyl, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio or C2-C3 alkoxycarbonyl; R 3 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy; or is benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; R 4is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, -C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, (CH2CH2O)tR 5 or benzyl or phenyl, wherein the ring in the benzyl or phenyl group is optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy; A compound of Formula 1 as described in the Summary of the Invention.

[0178] Embodiment B1. A compound according to embodiment B, A is A-1; R 1 is H, C1-C7 alkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy or benzyl; R 2 is H, halogen, —CN, C1-C4 alkyl, C3-C5 cycloalkyl, C1-C3 haloalkyl, C2-C4 alkoxyalkyl or C1-C3 alkoxy; R 3is H, C1-C4 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl or C1-C7 alkoxy; R 4 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl or C1-C7 alkoxy; each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 and X 9 But, CR 7 and; Each R 7 are independently H, halogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, or C1-C3 alkoxy; X is a direct bond or O; A compound according to embodiment B.

[0179] Embodiment B2. A compound according to embodiment B1, R 1 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl, C2-C3 cyanoalkyl, C1-C3 haloalkyl or C2-C4 alkoxyalkyl; R 2 is H, halogen, C1-C3 alkyl, cyclopropyl, C1-C2 haloalkyl, methoxy or ethoxy; R 3 is H, C1-C4 alkyl, C3-C7 haloalkyl, C4-C7 cycloalkyl, or C1-C7 alkoxy; Each R7 are independently H, halogen, C1-C2 alkyl, cyclopropyl, or C1-C2 haloalkyl; A compound according to embodiment B1.

[0180] Embodiment B3. A compound according to embodiment B2, R 1 is methyl, ethyl, n-propyl or 2-methoxyethyl; R 2 is H, F, Cl, methyl, ethyl, n-propyl, CF3 or methoxy; Each R 7 is independently H, halogen, methyl, ethyl or CF3; A compound according to embodiment B2.

[0181] Embodiment C1. A compound of Formula 1 as described in the Summary of the Invention or any one of the preceding embodiments, wherein R3 is H, R14 is H, X is a direct bond, and R4 is H, methyl, ethyl, i-propyl, t-Bu or methoxy, and which has improved herbicidal activity against certain weeds.

[0182] Embodiment C2. A compound according to embodiment C1 wherein the weed is Galium, Ambrosia, Amaranthus, Bassia, or Erigeron.

[0183] Embodiment C2a. A compound according to embodiment C1, wherein the weed is Galium aparine, Ambrosia artemisiifolia, Amaranthus palmeri, Bassia scoparia, or Erigeron canadensis.

[0184] Embodiment C2b. A compound according to Embodiment C1 wherein the weed is Galium, ragweed, pigweed, kochia, or artemisia.

[0185] Embodiment C3.R 3 is H and R 14 is H, X is a direct bond, and R 4 is H, methyl, ethyl, i-propyl, t-Bu or methoxy and have an improved tox profile.

[0186] Embodiment C4.R 3 is H and R 14 is H, X is a direct bond, and R 4 is H, methyl, ethyl, i-propyl, t-Bu or methoxy, and have improved pharmacokinetic properties.

[0187] Embodiment D. Compounds of Formula 1 as described in the Summary of the Invention, their stereoisomers and salts, agricultural compositions containing them, and their use as herbicides. Certain embodiments include compounds of Formula 1 selected from the group consisting of: 5-[(acetyloxy)methoxy]-6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-2-methyl-3(2H)-pyridazinone; 5-[(acetyloxy)methoxy]-4-(2-bromo-5-fluorobenzo[b]thien-3-yl)-2,6-dimethyl-3(2H)-pyridazinone; [[5-(2-fluoro-7-methyl-9-anthracenyl)-1,6-dihydro-1,3-dimethyl-6-oxo-4-pyridazinyl]oxy]methyl methyl carbonate; 5-[(acetyloxy)methoxy]-6-chloro-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2H)-pyridazinone; and 5-[(acetyloxy)methoxy]-4-(2-fluoro-7-methyl-9-anthracenyl)-2,6-dimethyl-3(2H)-pyridazinone.

[0188] The present invention also relates to a method for controlling undesirable vegetation, which comprises applying an effective amount of a compound of the present invention as a herbicide (e.g., as a composition described herein).Notable embodiments related to the method of use include compounds of the above-described embodiments.The compounds of the present invention are particularly useful for selectively controlling weeds in crops such as wheat, barley, corn, soybean, sunflower, cotton, oilseed rape, and rice, as well as specialty crops such as sugarcane, citrus, fruit, and nut crops.

[0189] Also of note as an embodiment are herbicidal compositions of the present invention that include compounds of the above-described embodiments.

[0190] The present invention further includes herbicidal mixtures comprising: (a) a compound selected from Formula 1, their N-oxides, and salts; and (b) at least one additional active ingredient, selected from: (b1) a photosystem II inhibitor, (b2) an acetohydroxyacid synthase (AHAS) inhibitor, (b3) an acetyl-CoA carboxylase (ACCase) inhibitor, (b4) an auxin mimetic, (b5) a 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitor, (b6) a photosystem I electron diverter, (b7) a protoporphyrinogen oxidase (PPO) inhibitor, (b8) a glutamine synthetase (GS) inhibitor, (b9) a very long chain fatty acid (VLCFA) elongase inhibitor, (b10). Auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solanesyltransferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides (including mitotic disruptors, organic arsenic compounds, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanide, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefon, pelargonic acid, and pyributicarb), (b16) herbicide safeners, and salts of the compounds (b1) to (b16).

[0191] "Photosystem II inhibitors" (b1) are compounds that bind to the D-1 protein at the QB-binding niche, thereby blocking electron transport from QA to QB in the thylakoid membrane of chloroplasts. Blocked electrons from the pathway through photosystem II are transported through a series of reactions to form toxic compounds that disrupt the cell membrane, leading to chloroplast swelling, membrane leakage, and ultimately cell destruction. The QB-binding niche has three distinct binding sites. Site A binds triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil; site B binds phenylureas such as diuron; and site C binds benzothiadiazoles such as bentazone, nitriles such as bromoxynil, and phenylpyridazines such as pyridate. Examples of photosystem II inhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil, bromofenoxime, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxyuron, cumyluron, cyanazine, dymron, desmedipham, desmetrin, dimefuron, dimethamethrin, diuron, ethidimuron, fenuron, fluometuron, hexazinone, and ioxynil. ru, isoproturon, isouron, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, methoxyuron, metribuzin, monolinuron, nebron, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, and trietazine.

[0192] "AHAS inhibitors" (b2) are compounds that inhibit acetohydroxyacid synthase (AHAS), also known as acetolactate synthase (ALS), and cause plant death by preventing the production of branched-chain aliphatic amino acids, such as valine, leucine, and isoleucine, which are required for protein synthesis and cell growth.Examples of AHAS inhibitors include: amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium, foramsulfuron, and halosulfuron. -methyl, imazametabunzu-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide), mezosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxazole) 2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), metosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxime, pyrif Thalide, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl, and tritosulfuron.

[0193] "ACCase inhibitors" (b3) are compounds that inhibit the enzyme acetyl-CoA carboxylase, which catalyzes an early step in the synthesis of lipids and fatty acids in plants. Lipids are essential components of cell membranes, without which new cells cannot be produced. Inhibition of acetyl-CoA carboxylase and the subsequent lack of lipid production leads to a loss of cell membrane integrity, especially in active growth zones, such as meristems. Ultimately, shoot and root growth ceases, and shoot meristems and root buds begin to wither. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim, and tralkoxydim (including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P, and quizalofop-P, and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, and fenoxaprop-P-ethyl).

[0194] Auxin is a plant hormone that regulates growth in many plant tissues. "Auxin mimetics" (b4) are compounds that mimic the plant growth hormone auxin, resulting in uncontrolled and unregulated growth and, in sensitive species, plant death. Examples of auxin mimetics include: aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clasifos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dicloprop, fluroxypyr, halaxifene (4-amino-3-chloro-6-(4-chloro- 2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), halaxifene-methyl (methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, triclopyr, and methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.

[0195] "EPSP synthase inhibitors" (b5) are compounds that inhibit 5-enol-pyruvylshikimate-3-phosphate synthase, an enzyme involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan, and phenylalanine. EPSP-inhibiting herbicides are readily absorbed through plant leaves and translocated to the growing point via the phloem. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium), and trimesium (also known as sulfosate).

[0196] "Photosystem I electron diverters" (b6) are compounds that accept electrons from photosystem I and, after several cycles, generate hydroxyl radicals. These radicals are highly reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This disrupts the integrity of cell membranes, resulting in "leaks" in cells and organelles, rapid wilting and drying of leaves, and ultimately plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.

[0197] "PPO inhibitors" (b7) are compounds that inhibit the enzyme protoporphyrinogen oxidase, causing the rapid production of highly active compounds in plants that disrupt cell membranes and leak cell fluids. Examples of PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, clomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, and pyraflufen-ethyl. , saflufenacil, sulfentrazone, thidiazimine, trifludimoxadine (dihydro-1,5-dimethyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione), and thiafenacil (methyl N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate).

[0198] "GS inhibitors" (b8) are compounds that block the activity of the glutamine synthetase enzyme, which plants use to convert ammonia to glutamine. Thus, ammonia accumulates and glutamine levels decrease. Damage to the plant may result from the combined effects of ammonia toxicity and a lack of amino acids needed for other metabolic processes. GS inhibitors include glufosinate and its esters and salts, such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid), and viranaphos.

[0199] "VLCFA elongase inhibitors" (b9) are herbicides with a wide variety of chemical structures that inhibit elongase, an enzyme located in or near chloroplasts that is involved in the biosynthesis of VLCFAs. In plants, very long-chain fatty acids are the main components of hydrophobic polymers that prevent desiccation on the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilophos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)-N,N-diethyl-2-(1-naphthalenyloxy)propanamide), petoxamide, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor (including resolved forms, such as S-metolachlor, and chloroacetamides and oxyacetamides).

[0200] "Auxin transport inhibitors" (b10) are chemical substances that inhibit the transport of auxin in plants, for example, by binding to auxin transport proteins. Examples of auxin transport inhibitors include diflufenzopyr and naptalam (also known as N-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid).

[0201] "PDS inhibitors" (b11) are compounds that inhibit the carotenoid biosynthetic pathway at the phytoene desaturase step. Examples of PDS inhibitors include: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurzone, and picolinafen.

[0202] "HPPD inhibitors" (b12) are chemical substances that inhibit the biosynthesis of 4-hydroxyphenyl-pyruvate dioxygenase. Examples of HPPD inhibitors include: benzobicyclone, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3 -cyclohexanedione), isoxachlorthol, isoxaflutole, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate (1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethyl methyl carbonate), topramezone, 5-chloro-3-[(2-hydroxy -6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydro [oxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide, and 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.

[0203] "HST (homogentisic acid solanesyltransferase) inhibitors" (b13) disrupt the plant's ability to convert homogentisic acid to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include cyclopyrimorate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), haloxidine, pyrichlor, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one, and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.

[0204] HST inhibitors also include compounds of formula A and B: [ka] In the formula, Rd 1 is H, Cl or CF3; Rd 2 is H, Cl or Br; Rd 3 is H or Cl; Rd 4 is H, Cl or CF3; Rd 5 is CH3, CH2CH3 or CH2CHF2; and Rd 6 is OH, or —OC(═O)-i-Pr; and Re 1 is H, F, Cl, CH3 or CH2CH3; Re 2 is H or CF3; Re 3 is H, CH3 or CH2CH3; Re 4 is H, F or Br; Re 5 is Cl, CH3, CF3, OCF3 or CH2CH3; Re 6 is H, CH3, CH2CHF2 or C≡CH; Re 7is OH, —OC(═O)Et, —OC(═O)-i-Pr or —OC(═O)-t-Bu; and Ae 8 is N or CH.

[0205] "Cellulose biosynthesis inhibitors" (b14) inhibit the biosynthesis of cellulose in certain plants. They are most effective when applied to young plants or rapidly growing plants before or shortly after emergence. Examples of cellulose biosynthesis inhibitors include: chlorthiamid, dichlobenil, furopoxam, indaziflam (N 2 -[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben, and triaziflam.

[0206] "Other herbicides" (b15) include herbicides that function through a variety of different modes of action, such as: mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl), organoarsenic compounds (e.g., DSMA and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors, and cell wall biosynthesis inhibitors. Other herbicides also include herbicides with no known mode of action or that do not fall into the specific categories listed in (b1) through (b14), or that operate through a combination of the modes listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cimmerin, clomazone, cumyluron, dymron, difenzoquat, etobenzanide, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dimron, ipfencarbazone (1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide), metam, methyl dimron, oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole. "Other herbicides" (b15) are also compounds of formula (b15A), [ka] During the ceremony, R 12 is H, C1-C6 alkyl, C1-C6 haloalkyl, or C4-C8 cycloalkyl: R 13 is H, C1-C6 alkyl or C1-C6 alkoxy; Q 1is an optionally substituted ring system selected from the group consisting of phenyl, thienyl, pyridinyl, benzodioxolyl, naphthyl, naphthalenyl, benzofuranyl, furanyl, benzothiophenyl, and pyrazolyl, and when substituted, the ring system is selected from the group consisting of 1 to 3 R 14 is replaced by; Q 2 is an optionally substituted ring system selected from the group consisting of phenyl, pyridinyl, benzodioxolyl, pyridinonyl, thiadiazolyl, thiazolyl, and oxazolyl, and when substituted, the ring system is 15 is replaced by; Each R 14 are independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C8 sialoalkyl, cyano, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, SF5, NHR 17 or 1 to 3 R 16 phenyl optionally substituted with 1 to 3 R 16 is a pyrazolyl substituted with; Each R 15 are independently halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, cyano, nitro, C1-C6 alkylthio, C1-C6 alkylsulfinyl, or C1-C6 alkylsulfonyl; Each R 16 are independently halogen, C1-C6 alkyl, or C1-C6 haloalkyl; R 17 is a C1-C4 alkoxycarbonyl.

[0207] In one embodiment, where "other herbicides" (b15) also include compounds of formula (b15A), R 12 is preferably H or C1-C6 alkyl, and more preferably R 12 is H or methyl. Preferably, R 13 is H. Preferably, Q 1is either a phenyl ring or a pyridinyl ring, and each ring has 1 to 3 R 14 and more preferably, Q 1 is 1 to 2 R 14 Preferably, Q is a phenyl ring substituted with 2 is 1 to 3 R 15 and more preferably, Q 2 is 1 to 2 R 15 Preferably, each R 14 are independently halogen, 1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy, more preferably each R 14 are independently chloro, fluoro, bromo, C1-C2 haloalkyl, C1-C2 haloalkoxy, or C1-C2 alkoxy. Preferably, each R 15 are independently halogen, C1-C4 alkyl, C1-C3 haloalkoxyhaloalkoxy; more preferably, each R 15 are independently chloro, fluoro, bromo, C1-C2 haloalkyl, C1-C2 haloalkoxy, or C1-C2 alkoxy. Specific preferred examples of the "other herbicide" (b15) include any one of the following (b15A-1) to (b15A-15). [ka] [ka] [ka]

[0208] "Other herbicides" (b15) are also compounds of formula (b15B), [ka] During the ceremony, R 18is H, C1-C6 alkyl, C1-C6 haloalkyl, or C4-C8 cycloalkyl: Each R 19 are independently halogen, C1-C6 haloalkyl, or C1-C6 haloalkoxy; p is an integer of 0, 1, 2, or 3; Each R 20 are independently halogen, C1-C6 haloalkyl, or C1-C6 haloalkoxy; q is an integer of 0, 1, 2 or 3.

[0209] In one embodiment, where "other herbicides" (b15) also include compounds of formula (b15B), R 18 is preferably H, methyl, ethyl or propyl, more preferably R 18 is H or methyl, and most preferably R 18 is H. Preferably, each R 19 are independently chloro, fluoro, C1-C3 haloalkyl or C1-C3 haloalkoxy, more preferably each R 19 is independently chloro, fluoro, C1 fluoroalkyl (i.e., fluoromethyl, difluoromethyl, or trifluoromethyl), or C1 fluoroalkoxy (i.e., trifluoromethoxy, difluoromethoxy, or fluoromethoxy). Preferably, each R 20 are independently chloro, fluoro, C1 haloalkyl or C1 haloalkoxy, more preferably each R 20 are independently chloro, fluoro, C1 fluoroalkyl (i.e., fluoromethyl, difluoromethyl, or trifluoromethyl), or C1 fluoroalkoxy (i.e., trifluoromethoxy, difluoromethoxy, or fluoromethoxy). Specific preferred examples of "other herbicides" (b15) include any one of the following (b15B-1) to (b15B-19). [ka] [ka] [ka] [ka]

[0210] Another embodiment in which "other herbicides" (b15) also includes compounds of formula (b15C): [ka] In the formula, R 1 is Cl, Br or CN, and R 2 is C(=O)CH2CH2CF3, CH2CH2CH2CH2CF3 or 3-CHF2-isoxazol-5-yl.

[0211] "Herbicide safeners" (b16) are substances added to herbicide formulations to eliminate or reduce the phytotoxic effects of the herbicide on certain crops. These compounds protect the crop from herbicide damage but typically do not prevent the herbicide from controlling undesirable vegetation. Examples of herbicide safeners include, but are not limited to, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, dymron, dichlormid, dicyclonone, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, and N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone, and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide.

[0212] For better control of undesirable vegetation (e.g., lower application rates, such as more than additive effects, a broader spectrum of weeds controlled, or improved crop safety) or to prevent the emergence of resistant weeds, preferred are mixtures of the compounds of the invention with a herbicide selected from the group consisting of atrazine, azimsulfuron, beflubutamid, beflubutamid-M, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, cloransulam-methyl, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-isoxazolidinone, 2-[(2,5 ... Methyl]-4,4-dimethyl-isoxazolidinone, ethametsulfuron-methyl, flumetoslam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,4H)-dione, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, metribuzin, metsulfuron-methyl, petoxamide, picloram, pyroxasulfone, quinclorac, rimsulfuron, S-metolachlor, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl, and tribenuron-methyl.

[0213] To prepare compounds of formula 1, one or more of the following methods and variations described in Schemes 1-9 can be used. R in compounds of formulas 1-12 below 1 , R 2 , R 3 , R 4 The definitions of X, A, and X are as defined above in the Summary of the Invention unless otherwise indicated. The compounds of formulae 1a, 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 6b, and 6c are various subsets of the compounds of formulae 1, 3, and 6; and all substituents of formulae 1a, 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 6b, and 6c are as defined above for formula 1 unless otherwise indicated in the disclosure, including the schemes.

[0214] As shown in Scheme 1, a compound of formula 1a (i.e., R 14 Compounds of formula 1 where Z is H) can be prepared by reacting a substituted 5-hydroxy-3(2H)-pyridazinone of formula 2 with a suitable electrophile of formula 3 (where Z is a leaving group, alternatively known as a nucleophile, e.g., a halogen) in the presence of a base in a suitable solvent. [ka]

[0215] Examples of suitable bases for the Scheme 1 reaction include, but are not limited to, potassium carbonate, cesium carbonate, sodium hydride, triethylamine, or potassium tert-butoxide. Depending on the specific base used, suitable solvents can be protic or aprotic and can be used as anhydrous or aqueous mixtures. Preferred solvents for this reaction include acetonitrile, tetrahydrofuran, 1,2-dimethoxyethane, dioxane, acetone, N,N-dimethylacetamide, or N,N-dimethylformamide. The reaction can typically be carried out at temperatures ranging from 0°C to the reflux temperature of the solvent. The use of a catalyst such as potassium iodide or sodium iodide can be advantageous when Z is Cl. The amount of such a catalyst used in the Scheme 1 reaction typically ranges from 0.1 to 1 molar equivalent. The use of iodide catalysis in the Scheme 1 reaction results in the in situ generation of compounds of Formula 3 where Z is I. Representative examples of reactions similar to the Scheme 1 reaction can be found in J. Med. Chem. 2004, vol. 47, pp. 5690-5699; J. Med. Chem. 2015, vol. 58, pp. 8154-8165; Tetrahedron Lett., 2015, vol. 56, pp. 5441-5444, and Tetrahedron Lett. 2016, vol. 57, pp. 1619-1621.

[0216] The preparation of compounds of Formula 2 is described in U.S. Pat. No. 10,118,917, U.S. Pat. No. 10,750,743, and U.S. Patent Application Publication No. 2020 / 0109123.

[0217] Many compounds of formula 3 are available from commercial sources. Scheme 2 illustrates the synthesis of compounds of formula 3a (i.e., R 3 A general method for preparing compounds of formula 3 (wherein X is H, X is a direct bond, and Z is Cl) is shown. As shown in Scheme 2, a carboxylic acid of formula 4 is reacted with chloromethyl chlorosulfate of formula 5 in the presence of a base, including but not limited to, sodium bicarbonate or sodium carbonate, in a solvent, including but not limited to, dichloromethane, tetrahydrofuran, ethyl acetate, acetonitrile, and toluene. In some examples, the use of a phase transfer catalyst, along with water as a co-solvent, is described. Typical phase transfer catalysts include, but are not limited to, tetra(n-butyl)ammonium hydrogen sulfate, tetra(n-butyl)ammonium iodide, and N-benzyl-N,N,N-triethylammonium chloride. The reaction can be carried out at temperatures ranging from 0°C to the reflux temperature of the solvent. Examples of the reaction of Scheme 2 can be found in Syn. Comm. 1984, vol. 14, pp. 857-864; Syn. Comm. 1994, vol. 24, pp. 767-772 and Bioorganic and Med. Chem. 2006, vol. 14, pp. 2569-2580. [ka]

[0218] Alternatively, compounds of formula 3b (i.e., compounds of formula 3 where X is a direct bond and Z is Cl) or compounds of formula 3c (i.e., compounds of formula 3 where X is a direct bond and Z is Br) can be prepared by reacting an acid chloride of formula 6b or an acid bromide of formula 6c with an aldehyde of formula 7, as shown in Scheme 3. As shown in Scheme 3, compounds of formula 6b or 6c and 7 are typically used in equimolar amounts, and zinc chloride or zinc bromide is typically used in an amount ranging from 0.1 to 2.0 molar equivalents. Typical solvents include dichloromethane, chloroform, and acetonitrile. The reaction temperature can range from -20°C to the reflux temperature of the solvent. Representative examples of reactions can be found in J. Med. Chem. 2009, vol. 52, pp. 771-778; Bioorganic and Med. Chem. Lett. 2014, vol. 24, pp. 5587-5592; and J. Org. Chem. 1993, vol. 58, pp. 588-599. [ka]

[0219] Compounds of formula 3d (i.e., compounds of formula 3 where X is a direct bond and Z is I) can be prepared by reacting compounds of formula 3b with iodides such as potassium iodide, sodium iodide, etc. in a solvent including, but not limited to, acetone, acetonitrile, or dichloromethane at temperatures ranging from ambient temperature to the reflux temperature of the solvent, as shown in Scheme 4. A representative example of the Scheme 5 reaction can be found in J. Am. Chem. Soc. 2001, vol. 133, pp. 8139-8140. [ka]

[0220] As shown in Scheme 5, compounds of formula 3e (i.e., compounds of formula 3 where X is O and Z is Cl) can be prepared by the reaction of a chloroformate of formula 9 with an alcohol of formula 10, as shown in Scheme 5. The alcohol of formula 10 is typically used in the range of 0.5 to 10 molar equivalents with a proton acceptor (such as, but not limited to, pyridine, triethylamine, or potassium carbonate) in a solvent such as, but not limited to, dichloromethane, tetrahydrofuran, water, or diethyl ether at a temperature ranging from 0° C. to the reflux temperature of the solvent. Representative examples can be found in J. Med. Chem. 2009, vol. 52, pp. 771-778 and Bioorg. And Med. Chem. Lett. 1997, vol. 7, pp. 1811-1816. [ka]

[0221] Compounds of formula 3f (i.e., compounds of formula 3 where X is S and Z is Cl) can be prepared by the reaction of a chloroformate of formula 9 with a thiol of formula 11, as shown in Scheme 6. The conditions for the reaction in Scheme 6 are similar to those used in the reaction in Scheme 5. Representative procedures can be found in Synthesis 1990, pp. 1159-1166 and J. Med. Chem. 2017, vol. 60, pp. 7136. [ka]

[0222] Compounds of formula 3g (i.e., where X is NR 6and Z is Cl) can be prepared as shown in Scheme 7 using methods similar to those described for the reactions of Scheme 5 and Scheme 6. Representative procedures can be found in Tetrahedron Lett 1999, vol. 40, pp. 607-610, Bioorg. Med. Chem. Lett. 2015, vol. 25, pp. 4987-4991 and Eur. J. Pharm. Sci. 2015, vol. 72, pp. 69-80. [ka]

[0223] Compounds of formula 9 can be prepared by reacting an aldehyde of formula 7 with phosgene or a phosgene equivalent, such as trichloromethyl chloroformate (also called diphosgene) or bis(trichloromethyl)carbonate (also called triphosgene), in the presence of 0 to 10 molar equivalents of a base, such as pyridine, in a solvent such as carbon tetrachloride, diethyl ether, or tetrahydrofuran, typically at a temperature ranging from −40° C. to ambient temperature, as shown in Scheme 8. Representative examples can be found in Tetrahedron Lett. 1989, vol. 30, pp. 2033-2036 and Synthesis 2002, pp. 365-370. [ka]

[0224] Preparation of compounds of formula 3i (i.e., compounds of formula 3 where Z is I) can be achieved by reacting compounds of formula 3h (i.e., compounds of formula 3 where Z is Cl) with 1 to 20 molar equivalents of an iodide source, such as, but not limited to, sodium iodide or potassium iodide, in a solvent such as, but not limited to, acetone, acetonitrile, and dichloromethane, as shown in Scheme 9. The reaction is typically carried out at temperatures ranging from ambient temperature to the reflux temperature of the solvent. [ka]

[0225] Those skilled in the art will appreciate that various functional groups can be converted into other groups to provide different compounds of Formula 1. A valuable resource demonstrating simple and straightforward functional group interconversions can be found in Larock, R.C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. For example, intermediates for preparing compounds of Formula 1 may contain an aromatic nitro group, which can be reduced to an amino group and then converted to various halides via reactions well known in the art, such as the Sandmeyer reaction, to provide compounds of Formula 1. The reactions described above can often be performed in different orders.

[0226] It is recognized that some of the reagents and reaction conditions described above for preparing compounds of Formula 1 may be incompatible with certain functional groups present in those intermediates. In these cases, incorporating protection / deprotection sequences into the synthesis or functional group interconversions may aid in obtaining the desired reaction products. The use and selection of protecting groups will be apparent to those familiar with chemical synthesis (see, for example, Greene, TW; Wuts, PGM, Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). As those skilled in the art will recognize, in some cases, completing the synthesis of compounds of Formula 1 may require the performance of additional conventional synthetic steps not specifically described after the introduction of certain reactants shown in the various individual schemes. As those skilled in the art will also recognize, it may be necessary to combine and perform the steps illustrated in the above schemes in an order other than the specific order presented to prepare compounds of Formula 1.

[0227] Those skilled in the art will further recognize that the compounds of Formula 1 and intermediates described herein can also be subjected to a variety of electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

[0228] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following non-limiting examples illustrate the present invention. The steps in the following examples describe the procedure for each step in an overall synthetic transformation, and the starting material for each step does not necessarily have to be prepared by the specific preparative procedure whose procedure is described in another example or step. Percentages are by weight unless otherwise indicated, except in the case of chromatographic solvent mixtures. In the case of chromatographic solvent mixtures, parts and percentages are by volume unless otherwise specified. Unless otherwise indicated, all NMR spectra are reported in CDCl3 downfield from tetramethylsilane at 500 MHz, where s means singlet, brs means broad singlet, d means doublet, t means triplet, and m means multiplet. [Example]

[0229] Synthesis Example 1 Preparation of 5-[(acetyloxy)methoxy]-6-chloro-4-(4-chloro-2-methylbenzo[b]thien-3-yl)-2-methyl-3(2H)-pyridazinone (i.e., Compound 1) Step A: Preparation of 6-chloro-5-[(4-chlorobenzo[b]thien-2-yl)methoxy]-2-methyl-3(2H)-pyridazinone To a stirred solution of 5,6-dichloro-2-methyl-pyridazin-3-one (900 mg, 5.0 mmol), (4-chlorobenzothiophen-2-yl)methanol (1.0 g, 5.0 mmol) in anhydrous N,N-dimethylformamide (20 mL) was added sodium hydride (260 mg, 60% in oil, 6.5 mmol) at 0° C. The resulting mixture was stirred at 25° C. for 18 hours and then poured into saturated aqueous ammonium chloride solution. The resulting mixture was extracted with ethyl acetate (4 times), and the combined organic layers were washed with water and brine. A white solid precipitate formed in the organic layer. The organic layer was filtered, and the white solid product was dried under vacuum to give the title compound (1.3 g, 76%). 1 H NMR(CDCl3)δ 7.72(d,1H),7.55(s,1H),7.38(d,1H),7.30(m,2H),6.33(s,1H),5.36(s,2H),3.70(s,3H).

[0230] Step B: Preparation of 6-chloro-4-(4-chloro-2-methylbenzo[b]thien-3-yl)-5-hydroxy-2-methyl-3(2H)-pyridazinone A solution of 6-chloro-5-[(4-chlorobenzo[b]thien-2-yl)methoxy]-2-methyl-3(2H)-pyridazinone (i.e., the product of Step A) (1.3 g, 3.8 mmol) in xylene (5 mL) was heated to reflux for 48 hours. The resulting mixture was cooled to 25° C. and diluted with hexane. The resulting mixture was filtered, and the solid product was washed several times with hexane and dried to give the title compound as a tan solid (0.60 g, 46%). 1 1 H NMR showed acceptable purity and the crude product was used in the next step without further purification.

[0231] Step C: Preparation of 5-[(acetyloxy)methoxy]-6-chloro-4-(4-chloro-2-methylbenzo[b]thien-3-yl)-2-methyl-3(2H)-pyridazinone To a stirred solution of 6-chloro-4-(4-chloro-2-methylbenzo[b]thien-3-yl)-5-hydroxy-2-methyl-3(2H)-pyridazinone (i.e., the product from Step B) (110 mg, 0.32 mmol), chloromethyl acetate (0.11 mL, 1.25 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added sodium hydride (13 mg, 60% in oil, 0.32 mmol) at 25 °C. The resulting mixture was stirred at 60 °C for 18 h, cooled to 25 °C, and poured into saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (4 times), and the combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated. Chromatography on silica gel eluting with a gradient of 0% to 100% ethyl acetate in hexanes afforded the title product as a yellow solid (21 mg, 16%). 1 H NMR(CDCl3)δ 7.69(m,1H),7.31(m,1H),7.19-7.24(m,1H),5.27-5.30(m,2H),3.80(s,3H),2.37(s,3H),1.74(s,3H).

[0232] Synthesis Example 2 Preparation of 5-[(acetyloxy)methoxy]-6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-2-methyl-3(2H)-pyridazinone (i.e., Compound 3) To a stirred solution of 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone (120 mg, 0.38 mmol, prepared as described in WO2020069057) and chloromethyl acetate (170 mg, 1.6 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added sodium hydride (63 mg, 60% in oil, 1.6 mmol) at 25 °C. The resulting mixture was stirred at 60 °C for 18 h, then cooled to 25 °C and poured into saturated aqueous ammonium chloride solution. The resulting mixture was extracted with ethyl acetate (3 times), and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated. Chromatography of the crude product on silica gel eluting with a gradient of 30% to 100% ethyl acetate in hexanes afforded the title compound as a yellow oil (60 mg, 41%). 1 H NMR(CDCl3)δ 7.79(m,1H),7.73(m,1H),7.34(m,1H),7.25-7.30(m,1H),7.16(s,1H),5.0 3(m,1H),4.93(m,1H),3.84(s,3H),2.45(s,3H),2.32(s,3H),1.82(s,3H).

[0233] Synthesis Example 3 Preparation of [[3-chloro-5-(2,7-dimethyl-9-anthracenyl)-1,6-dihydro-1-methyl-6-oxo-4-pyridazinyl]oxy]methyl methyl carbonate (i.e., compound 8) Step A: Preparation of methyl 5-methyl-2-(p-tolylmethyl)benzoate Zinc dust (16.0 g, 245 mmol) was suspended in anhydrous tetrahydrofuran (200 mL), and the resulting mixture was heated at 60° C. 1,2-Dibromoethane (0.8 mL) was added to the heated mixture, and the resulting mixture was stirred at 60° C. for 3 minutes, then cooled to 25° C. Chlorotrimethylsilane (0.8 mL) was added, and the resulting mixture was stirred at 25° C. for 3 minutes, then cooled to 5° C. A solution of 4-methylbenzyl bromide (22.7 g, 128 mmol) in anhydrous tetrahydrofuran (100 mL) was then added dropwise to the activated zinc suspension at a rate that maintained the reaction temperature below 16° C. The resulting mixture was stirred at 5°C for 1 hour and then treated with a solution of methyl 2-bromo-5-methylbenzoate (14.9 g, 64 mmol) in anhydrous tetrahydrofuran (100 mL) at a temperature below 10°C, followed by the addition of bis(triphenylphosphine)palladium(II) dichloride (860 mg, 1.23 mmol). The resulting mixture was stirred at ambient temperature for 18 hours and then poured into ice-cold saturated aqueous ammonium chloride solution. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting light brown oil was purified by silica gel chromatography eluting with a gradient of 0% to 30% ethyl acetate in hexane to afford the title compound (15.9 g, 96%) as a colorless oil. 1 H NMR(CDCl3)δ 7.69(s,1H),7.22(d,1H),7.10-7.00(m,5H),4.28(s,2H),3.82(s,3H),2.35(s,3H),2.29(s,3H).

[0234] Step B: Preparation of 5-methyl-2-(p-tolylmethyl)benzoic acid Aqueous sodium hydroxide (50%, 10 mL) was added to a solution of methyl 5-methyl-2-(p-tolylmethyl)benzoate (i.e., the product of Step A) (15.9 g, 62.5 mmol) in ethanol (250 mL) at ambient temperature. After stirring for 2 days, the resulting mixture was concentrated to remove most of the ethanol. Water (300 mL) was added, and the resulting aqueous mixture was washed with diethyl ether (100 mL). The resulting aqueous mixture was cooled in an ice-water bath and acidified with concentrated hydrochloric acid dropwise with stirring until the pH reached 1-2. The resulting beige precipitate was filtered, and the solid product was washed with water and dried under vacuum. The title compound was obtained as a beige solid (14.4 g, 96%). 1 H NMR δ 7.86 (s, 1H), 7.28 (d, 1H), 7.11 (d, 1H), 7.06 (m, 4H), 4.77 (broadened s, 1H), 4.36 (s, 2H), 2.36 (s, 3H), 2.30 (s, 3H).

[0235] Step C: Preparation of 2,7-dimethyl-10H-anthracen-9-one With ice-water bath cooling, 5-methyl-2-(p-tolylmethyl)benzoic acid (i.e., the product of Step B) (14.4 g, 60 mmol) was added portionwise to neat concentrated sulfuric acid (120 mL). The resulting mixture was stirred at 25° C. for 2 hours and then poured into 500 mL of ice with stirring. The resulting suspension was filtered, and the resulting beige solid was washed with water. The resulting solid was dissolved in dichloromethane (300 mL), and the organic solution was washed with 1 N aqueous sodium hydroxide solution (2×), water, and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the title compound as a beige solid (8.0 g, 60%). 1 H NMR(CDCl3)δ 8.17(s,2H),7.42(dd,2H),7.36(d,2H),4.28(s,2H),2.46(s,6H).

[0236] Step D: Preparation of (2,7-dimethyl-9-anthryl)trifluoromethanesulfonate A solution of 2,7-dimethyl-10H-anthracen-9-one (3.4 g, 15 mmol) in dichloromethane (60 mL) was degassed by bubbling nitrogen gas through the solution for 10 minutes while cooling to 5° C. To the resulting solution was added DBU (3.4 mL, 23 mmol) at a rate that maintained the temperature below 10° C. To the resulting solution was added a solution of trifluoromethanesulfonic anhydride (3.2 mL, 19 mmol) and dichloromethane (15 mL) at a rate that maintained the temperature below 10° C. The resulting pale yellow solution was stirred at 25° C. for 2 hours and then poured into ice water. The aqueous layer was separated and extracted with dichloromethane, and the combined organic layers were washed with water, brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the crude product, which was purified by silica gel chromatography eluting with a gradient of 0% to 30% ethyl acetate in hexanes to give the title compound as a beige solid (4.1 g, 76%). 1 H NMR(CDCl3)δ 8.39(s,1H),7.95(s,2H),7.92(d,2H),7.35(d,2H),2.60(s,6H).

[0237] Step E: Preparation of 6-chloro-4-(2,7-dimethyl-9-anthracenyl)-5-methoxy-2-methyl-3(2H)-pyridazinone A solution of zinc chloride in 2-methyltetrahydrofuran (6.7 mL of a 1.9 M solution, 13 mmol) was added to a solution of 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex in tetrahydrofuran (25 mL of a 1.0 M solution, 25 mmol) at 5° C. The resulting solution was stirred at 25° C. for 1 hour, then cooled to −40° C. and treated with anhydrous tetrahydrofuran (25 mL) followed by 6-chloro-5-methoxy-2-methyl-pyridazin-3(2H)-one (2.0 g, 12 mmol, for preparation see J. Med. Chem. 2017, vol. 60, pp. 3828-3850). The resulting mixture was stirred at 0-5°C for 1 hour and then treated with a solution of (2,7-dimethyl-9-anthryl)trifluoromethanesulfonate (i.e., the product from Step D) (4.1 g, 12 mmol) in tetrahydrofuran (35 mL) added at 5°C. The resulting solution was treated with S-Phos-Pd-precatalyst-G2 (0.84 g, 1.2 mmol). The resulting mixture was stirred at 25°C for 18 hours and then treated with saturated aqueous ammonium chloride solution (100 mL). The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the crude product, which was purified by silica gel chromatography eluting with 0%-70% ethyl acetate in hexanes. The early eluting fractions contained recovered triflate starting material (i.e., 2.8 g of the product from Step D), followed by fractions containing the title compound as a pale yellow solid (1.2 g, 27%; or 86% based on recovered triflate starting material). 1 H NMR(CDCl3)δ 8.45(s,1H),7.92(d,2H),7.29(s,2H),7.27(d,2H),3.83(s,3H),3.07(s,3H),2.49(m,6H).

[0238] Step F: Preparation of 6-chloro-4-(2,7-dimethyl-9-anthracenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone A mixture of 6-chloro-4-(2,7-dimethyl-9-anthracenyl)-5-methoxy-2-methyl-3(2H)-pyridazinone (i.e., the product from Step E) (2.4 g, 6.3 mmol) and morpholine (12 mL) was heated at 110° C. for 1 hour. The resulting mixture was cooled to 0° C. and left at this temperature overnight. The resulting mixture was diluted with diethyl ether and filtered. The resulting pale orange solid was washed with ether and dried on a frit under nitrogen to give the desired product as the morpholine salt (2.1 g). The salt was suspended in a mixture of 1N aqueous hydrochloric acid (60 mL) and acetonitrile (10 mL), stirred for 1 hour, and filtered. The resulting solid was suspended in a solution of acetone (20 mL) and acetonitrile (10 mL) and heated to reflux to give a clear solution, which was then added dropwise with stirring to 1N aqueous hydrochloric acid (60 mL). The resulting solid was filtered, washed with water and dried under vacuum to give the title compound as a pale yellow solid (1.75 g, 76%). 1 H NMR(DMSO-d6)δ 11.0(br s,1H),8.57(s,1H),8.02(d,2H),7.38(s,2H),7.33(d,2H),3.68(s,3H),2.43(m,6H).

[0239] Step G: Preparation of [[3-chloro-5-(2,7-dimethyl-9-anthracenyl)-1,6-dihydro-1-methyl-6-oxo-4-pyridazinyl]oxy]methyl methyl carbonate A mixture of 6-chloro-4-(2,7-dimethyl-9-anthracenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone (i.e., the product from Step F) (100 mg, 0.27 mmol), chloromethyl methyl carbonate (68 mg, 0.55 mmol), potassium iodide (91 mg, 0.55 mmol), potassium carbonate (76 mg, 0.55 mmol), and acetonitrile (4.6 mL) was stirred at 55° C. under N. After heating for 16 h, the reaction was cooled to 25° C., diluted with dichloromethane, treated with 1.5 g of Celite, and concentrated. The resulting solid was purified by silica gel chromatography eluting with a gradient of 30% to 100% ethyl acetate in hexanes to give the title compound as a yellow semisolid (62 mg, 50%). 1 H NMR(CDCl3)δ 8.47(s,1H),7.92(d,2H),7.31(s,2H),7.29(d,2H),4.78(s,2H),3.88(s,3H),3.67(s,3H),2.49(m,6H).

[0240] Synthesis Example 4 Preparation of [[3-chloro-5-(2,7-dimethyl-9-anthracenyl)-1,6-dihydro-1-methyl-6-oxo-4-pyridazinyl]oxy]methyl 2,2-dimethylpropanoate (i.e., Compound 9) A mixture of 6-chloro-4-(2,7-dimethyl-9-anthracenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone (i.e., the product from Synthesis Example 3, Step F) (100 mg, 0.27 mmol), chloromethyl pivalate (83 mg, 0.55 mmol), potassium iodide (91 mg, 0.55 mmol), potassium carbonate (76 mg, 0.55 mmol), and acetonitrile (4.6 mL) was stirred at reflux for 18 hours. The resulting mixture was cooled to 25°C, diluted with ethyl acetate, treated with Celite (1.5 g), and concentrated. Chromatography on silica gel eluting with 20%-100% ethyl acetate in hexanes afforded the title compound as a yellow semisolid (125 mg, 95%). 1H NMR(CDCl3)δ 8.47(s,1H),7.93(d,2H),7.35(s,2H),7.29(d,2H),4.69(s,2H),3.86(s,3H),2.49(m,6H),1.07(s,9H).

[0241] Synthesis Example 5 Preparation of 5-[(acetyloxy)methoxy]-4-(9-anthracenyl)-6-chloro-2-methyl-3(2H)-pyridazinone (i.e., Compound 10) A mixture of 4-(9-anthracenyl)-6-chloro-5-hydroxy-2-methyl-3(2H)-pyridazinone (119 mg, 0.35 mmol, prepared as described in U.S. Patent Application Publication No. 2020 / 0109123), chloromethyl acetate (154 mg, 1.40 mmol), cesium carbonate (230 mg, 0.70 mmol), and sodium iodide (20 mg, 0.13 mmol) in acetone (5.4 mL) was heated to reflux. After heating for 16 h, the mixture was cooled to ambient temperature and concentrated onto celite (1.5 g). The resulting mixture was purified by MPLC on a 12 g silica gel column eluting with a gradient of 0% to 100% ethyl acetate in hexanes to afford 105 mg of the title compound as a yellow glassy solid. 1 H NMR δ 8.59(s,1H),8.07-8.04(m,2H),7.67-7.63(m,2H),7.51-7.47(m,4H),4.82(s,2H),3.87(s,3H),1.66(s,3H).

[0242] Synthesis Example 6 Preparation of 5-[(acetyloxy)methoxy]-6-chloro-4-(10-chloro-9-anthracenyl)-2-methyl-3(2H)-pyridazinone (i.e., Compound 11) A mixture of 6-chloro-4-(10-chloro-9-anthracenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone (159 mg, 0.43 mmol, prepared as described in U.S. Patent Application Publication No. 2020 / 0109123), chloromethyl acetate (140 mg, 1.29 mmol), cesium carbonate (279 mg, 0.83 mmol), and sodium iodide (13 mg, 0.08 mmol) in acetone (6.4 mL) was heated to reflux for 16 hours. The resulting mixture was cooled to ambient temperature and concentrated onto Celite® diatomaceous earth filter aid (1.5 g). The resulting mixture was purified by MPLC on a 12 g silica gel column eluting with a gradient of 0% to 100% ethyl acetate in hexanes to afford 140 mg of the title compound as a yellow glassy solid. 1 H NMR δ 8.60(d,2H),7.68(dt,2H),7.62(td,2H),7.53(td,2H),4.85(s,2H),3.87(s,3H),1.67(s,3H).

[0243] The compounds in Tables 1-1009 below can be prepared by the procedures described herein and 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 cyclo, 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, -NO means nitro, TMS means trimethylsilyl, SOMe means methylsulfinyl, CF means CF, and SOMe means methylsulfonyl. Table 1 [ka] X is a direct bond and R 1 is Me and R 2is Me, and (R 12 )n is 2,5-di-Me (phrase in header line)

[0244] [Table 1]

[0245] [Table 2]

[0246] [Table 3]

[0247] [Table 4]

[0248] [Table 5]

[0249] [Table 6]

[0250] [Table 7]

[0251] [Table 8]

[0252] [Table 9]

[0253] [Table 10]

[0254] [Table 11]

[0255] The disclosure also includes Tables 2 through 160, and the phrase in the header line of Table 1 (i.e., "X is a direct bond and R 1 is Me and R 2 is Me, and (R 12 )n is 2,5-di-Me) is replaced by the phrase in the header line listed in each table, and the remaining variables in each table, R 3 and R 4 is as defined in Table 1.

[0256] [Table 12]

[0257] [Table 13]

[0258] [Table 14]

[0259] [Table 15]

[0260] [Table 16]

[0261] [Table 17]

[0262] Table 161 [ka] The clause X in the header line is a direct join, and R 1 is Me and R 2 is Me, and (R 12 )n is H. The remaining variables (i.e., R 3 and R 4 ) are as defined in Table 1.

[0263] The disclosure also includes Tables 162-384, and the phrase in the header line of Table 161 (i.e., "X is a direct bond and R 1 is Me and R 2 is Me, and (R 12 )n is H”) is replaced by the phrase from the header line listed in each table, and the remaining variables are as defined in Table 1.

[0264] [Table 18]

[0265] [Table 19]

[0266] [Table 20]

[0267] [Table 21]

[0268] [Table 22]

[0269] [Table 23]

[0270] [Table 24]

[0271] Table 385 [ka] The clause X in the header line is a direct join, and R 1 is Me and R 2 is Me, and (R 12 )n is H. The remaining variables (i.e., R 3 and R 4 ) are as defined in Table 1.

[0272] The disclosure also includes Tables 386-816, and the phrase in the header line of Table 385 (i.e., "X is a direct bond and R 1 is Me and R 2 is Me, and (R 12 )n is H”) is replaced by the phrase from the header line listed in each table, and the remaining variables are as defined in Table 1.

[0273] [Table 25]

[0274] [Table 26]

[0275] [Table 27]

[0276] [Table 28]

[0277] [Table 29]

[0278] [Table 30]

[0279] [Table 31]

[0280] [Table 32]

[0281] [Table 33]

[0282] [Table 34]

[0283] [Table 35]

[0284] [Table 36]

[0285] [Table 37]

[0286] Table 817 [ka] The phrase in the header line: X is a direct bond and R 1 is Me and R 2 is Me, and (R 7 )n is H. The remaining variables (i.e., R3 and R 4 ) are as defined in Table 1.

[0287] The disclosure also includes Tables 818-912, and the phrase in the header line of Table 817 (i.e., "X is a direct bond and R 1 is Me and R 2 is Me, and (R 12 )n is H") is replaced by the phrase in the header line listed in each table, and the remaining variables (i.e., R 3 and R 4 ) are as defined in Table 1.

[0288] [Table 38]

[0289] [Table 39]

[0290] [Table 40]

[0291] [Table 41]

[0292] Table 913 [ka] The phrase in the header line: X is a direct bond and R 1 is Me and R 2 is Me, and (R 7 )n is H. The remaining variables (i.e., R 3 and R 4 ) are as defined in Table 1.

[0293] The disclosure also includes Tables 914-1008, and the phrase in the header line of Table 913 (i.e., "X is a direct bond and R 1 is Me and R 2 is Me, and (R 12 )n is H") is replaced by the phrase in the header line listed in each table, and the remaining variables (i.e., R 3 and R 4 ) are as defined in Table 1.

[0294] [Table 42]

[0295] [Table 43]

[0296] [Table 44]

[0297] [Table 45]

[0298] The present disclosure also includes the following Table 1009: Table 1009 [ka]

[0299] [Table 46]

[0300] [Table 47]

[0301] Formulation / Practical Use The compounds of the present invention will generally be used as the herbicidal active ingredient in a composition, i.e., a formulation, along with at least one additional ingredient selected from the group consisting of surfactants, solid diluents, and liquid diluents, which acts as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, the mode of application, and environmental factors such as soil type, moisture, and temperature.

[0302] Useful formulations include both liquid and solid compositions, including solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates, and / or suspoemulsions), which may optionally be thickened to form gels.

[0303] Common types of aqueous liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, flowable concentrates, and suspoemulsions. Common types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates, and oil dispersions. Common types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, and filled films (including seed coatings), which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatments. Active ingredients can be (micro)encapsulated and further formed into suspensions or solid formulations. Alternatively, the entire active ingredient formulation can be encapsulated (or "overcoated"). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of both emulsifiable concentrate and dry granule formulations. High-strength compositions are primarily used as intermediates for further formulation.

[0304] Sprayable formulations are typically spread in a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily diluted in the spray medium, usually water, but sometimes another suitable medium such as an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about 1 liter to several thousand liters per hectare, but more typically range from about 10 liters to several hundred liters per hectare. Sprayable formulations can be tank-mixed with water or other suitable medium for foliar treatment by aerial or ground application, or for application to plant growing media. Liquid and dry formulations can be injected directly into drip irrigation systems or into furrows at planting time.

[0305] Formulations will typically contain active ingredients, diluents, and surfactants within the following approximate ranges, which add up to 100 weight percent:

[0306] [Table 48]

[0307] Examples of solid diluents include clays such as bentonite, montmorillonite, attapulgite, kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, 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.

[0308] Examples of liquid diluents include water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oil, normal paraffin, isoparaffin), alkylbenzenes, alkylnaphthalenes, glycerin, glycerin triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatic hydrocarbons, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-pentaerythritol. Non-aqueous diluents include acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate, and isobornyl acetate, other esters such as alkylated lactates, dibasic esters, alkyl and aryl benzoates, and gamma-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. Liquid diluents include glycerol esters of saturated and unsaturated fatty acids (typically C6~C 22Liquid diluents also include glycerol esters of vegetable oils (e.g., olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut, and palm kernel oils), fats of animal origin (e.g., beef tallow, pork fat, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated), where the fatty acids can be obtained by hydrolysis of glycerol esters from vegetable and animal sources and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[0309] The solid and liquid compositions of the present invention often contain one or more surfactants. When added to a liquid, surfactants (also known as "surface active agents") generally modify, and most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in the surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers, or antifoaming agents.

[0310] Surfactants are classified as nonionic, anionic or cationic.The nonionic surfactants useful for the present composition include, but are not limited to, alcohol alkoxylates, such as those based on natural and synthetic alcohols (can be branched or linear) and prepared from alcohols and ethylene oxide, propylene oxide, butylene oxide or their mixtures; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides, such as ethoxylated soybean oil, linseed oil and rapeseed oil; alkylphenol alkoxylates, such as octylphenol ethoxylate, nonylphenol ethoxylate, dinonylphenol ethoxylate and dodecylphenol ethoxylate (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide or their mixtures); block polymers prepared from ethylene oxide or propylene oxide, and the end blocks of which are prepared from propylene oxide; reverse block polymers; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); fatty acid esters, 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 polymers, and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives such as sucrose esters, alkyl polyglycosides, and alkyl polysaccharides.

[0311] Useful anionic surfactants include, but are not limited to, alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonic acid derivatives; lignin and lignin derivatives such as lignosulfonates; maleic acid or succinic acid or anhydrides; olefin sulfonates, phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates, and phosphate esters of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfonates; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyl taurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecyl benzene; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalenes; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinate salts.

[0312] Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides; amines such as N-alkylpropanediamines, tripropylenetriamine, 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 oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

[0313] Also useful in the compositions of the present invention are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic, and cationic surfactants and their recommended uses are disclosed in various published 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.S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[0314] The compositions of the present invention may further include formulation aids and additives known to those skilled in the art as formulation aids, some of which may also be considered to function as solid diluents, liquid diluents, or surfactants. Such formulation aids and additives may control pH (buffers), foaming during processing (antifoaming agents such as polyorganosiloxanes), active ingredient settling (suspending agents), viscosity (thixotropic thickeners), microbial growth in the container (antimicrobial agents), product freezing (antifreeze agents), color (dye / pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation properties. Film formers include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation aids and additives include those described in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03 / 024222.

[0315] The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or milling 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 not miscible with water, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries having particle sizes up to 2,000 μm can be wet-milled using a media mill to obtain particles with an average particle size of less than 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, e.g., U.S. Pat. No. 3,060,084) or can be further processed by spray drying to form water-dispersible granules. Dry blends typically require a dry-milling step, which results in an average particle size in the range of 2 to 10 μm. Dusts and powders can be prepared by blending and typically milling (e.g., hammer mill or fluid energy mill). Granules and pellets can be prepared by spraying the active material onto a preformed granular carrier or by agglomeration techniques. 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 WO 91 / 13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, and German Patent No. 3,246,493. Tablets can be prepared as taught in U.S. Patent Nos. 5,180,587, 5,232,701, and 5,208,030. Films can be prepared as taught in British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

[0316] For further information on formulation techniques, see T. Swoods, "The Formulator's Toolbox - Product Forms for Modern Agriculture," in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also the following references: U.S. Pat. No. 3,235,361, column 6, line 16 to column 7, line 19, and Examples 10-41; U.S. Pat. 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. Pat. 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 Publications, Richmond, UK, 2000.

[0317] 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 elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. Accordingly, the following examples are intended to be merely illustrative and not limiting of the present disclosure in any way. Percentages are by weight unless otherwise specified.

[0318] Example A high strength concentrate Compound 2 98.5% Silica aerogel 0.5% Synthetic amorphous fine silica 1.0%

[0319] Example B Wettable Powder Compound 2 65.0% Dodecylphenol polyethylene glycol ether 2.0% Sodium lignosulfonate 4.0% Sodium silicoaluminate 6.0% Montmorillonite (calcined) 23.0%

[0320] Example C Granules Compound 2 10.0% Attapulgite Granules (low volatile content, 0.71 / 0.30 mm; USS No. 25-50 sieve) 90.0%

[0321] Example D Extruded pellets Compound 2 25.0% Anhydrous sodium sulfate 10.0% Crude calcium lignosulfonate 5.0% Sodium alkylnaphthalene sulfonate 1.0% Calcium / Magnesium Bentonite 59.0%

[0322] Example E Emulsifiable concentrate Compound 2 10.0% Polyoxyethylene sorbitol hexoleate 20.0% C6~C 10 Fatty acid methyl ester 70.0%

[0323] Example F Microemulsion Compound 2 5.0% Polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglycoside 30.0% Glyceryl monooleate 15.0% Water 20.0%

[0324] Example G Suspension concentrate Compound 2 35% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone antifoaming agent 0.1% 1,2-benzisothiazolin-3-one 0.1% Water 53.7%

[0325] Example H Emulsion in water Compound 2 10.0% Butyl polyoxyethylene / polypropylene block copolymer 4.0% Stearic acid / polyethylene glycol copolymer 1.0% Styrene acrylic polymer 1.0% Xanthan gum 0.1% Propylene glycol 5.0% Silicone antifoaming agent 0.1% 1,2-benzisothiazolin-3-one 0.1% Aromatic petroleum hydrocarbons 20.0 Water 58.7%

[0326] Example I oil dispersion Compound 2 25% Polyoxyethylene sorbitol hexaoleate 15% Organically modified bentonite clay 2.5% Fatty acid methyl esters 57.5%

[0327] The present disclosure also includes Examples A-I above, except that "Compound 2" is replaced with "Compound 1," "Compound 3," "Compound 4," "Compound 5," "Compound 6," "Compound 7," "Compound 8," "Compound 9," "Compound 10," "Compound 11," "Compound 12," "Compound 13," "Compound 14," "Compound 15," "Compound 16," "Compound 17," "Compound 18," "Compound 19," "Compound 20," "Compound 21," "Compound 22," "Compound 23," "Compound 24," "Compound 25," "Compound 26," "Compound 27," "Compound 28," "Compound 29," or "Compound 30."

[0328] The test results show 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 show the best activity in post-emergence weed control (i.e., applied after weed seedlings emerge from the soil) and pre-emergence weed control (i.e., applied before weed seedlings emerge from the soil).Many of them are useful for 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, airports, riverbanks, irrigation and other waterways, around large billboards, and railroad facilities. Many of the compounds of the present invention are useful for the selective control of grasses and broadleaf weeds in crop / weed mixtures because they have selective crop versus weed metabolism, or selective activity in areas of physiological inhibition in crops and weeds, or selective placement on or in the mixed crop and weed environment. As will be recognized by those skilled in the art, suitable combinations of selectivity factors within a single compound or group of compounds can be readily determined by routine biological and / or biochemical assays. The compounds of the invention may exhibit resistance to important agricultural crops such as, but not limited to, alfalfa, barley, cotton, wheat, rapeseed, sugar beet, corn (maize), sorghum, soybean, rice, oats, peas, vegetables, tomatoes, potatoes, perennial plantation crops (including coffee, cocoa, oil palm, rubber), sugarcane, citrus, grapeseed, fruit trees, nut trees, bananas, plantains, pineapples, hops, tea plants, and woodlands such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue, and cypress).The compounds of the present invention may be useful in genetically transformed crops, or crops bred to incorporate herbicide resistance, express proteins toxic to invertebrate pests (e.g., Bacillus thuringiensis toxins), and / or express other useful traits. As one of ordinary skill in the art will recognize, not all compounds are equally effective against all weeds. However, the compounds that are the subject of the present invention are useful for regulating plant growth.

[0329] Because the compounds of the present invention have both pre- and post-emergence herbicidal activity and control undesirable vegetation by killing or damaging the vegetation or inhibiting its growth, they can be usefully applied by various methods, including contacting a herbicidally effective amount of a compound of the present invention or a composition comprising a compound of the present invention and at least one surfactant, solid diluent, or liquid diluent with the foliage or other parts of the undesirable vegetation, or with the environment of the undesirable vegetation, such as soil or water, in which the undesirable vegetation is growing or surrounding the seeds or other propagules of the undesirable vegetation. The undesirable vegetation can include at least one species selected from the group consisting of grass weeds and broadleaf weeds. Unwanted vegetation includes annual bluegrass, spotted daygrass, blackgrass, black nightshade, broadleaf signalgrass, foxglove, bromegrass, cocklebur (Xanthium pensylvanicum), ragweed, corn poppy, field violet, foxtail, goosegrass, green foxtail, guineagrass, burdock, herbicide-resistant blackgrass, dwarf artemisia, Italian ryegrass, morning glory, Pennsylvania willow weed, morning glory, pea weed, quackgrass, red ragweed, sedge, shepherd's purse, and silky windgrass. windgrass, sunflower (as potato species), bindweed (Polygonum convolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua), wild poinsettia, golden foxtail, and tiger berry (Cyperus esculentus).

[0330] The herbicidally effective amount of the compounds of the present invention depends on several factors, including the formulation selected, the method of application, the amount and type of vegetation present, etc. In general, the herbicidally effective amount of the compounds of the present invention is about 0.001 to 20 kg / ha, with a preferred range being about 0.004 to 1 kg / ha. One skilled in the art can readily determine the herbicidally effective amount required to achieve the desired level of weed control.

[0331] In one general embodiment, the compounds of the invention, typically in the form of a formulated composition, are applied to an area 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 the growing medium (e.g., soil). In this area, compositions containing the compounds of the invention can be applied directly to the plants or parts thereof of the undesirable vegetation and / or to the growing medium in contact with the plants.

[0332] Although compounds of the invention are most typically used to control undesirable vegetation, contacting desirable vegetation with a compound of the invention in a treated area may result in superadditive or enhanced effects, including those derived from the genetic traits of the desirable vegetation and traits acquired through genetic modification. For example, resistance to herbivorous pests or plant diseases, resistance to biotic / abiotic stresses, or storage stability may be greater than would be expected from the genetic traits of the desirable vegetation.

[0333] The compounds of the present invention can also be mixed with one or more other biologically active compounds or agents, including herbicides, herbicide safeners, fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators such as insect molting inhibitors and root stimulators, chemosterilants, signal chemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds, or insect pathogenic bacteria, viruses, or fungi, to form multi-component biocides that provide broader agricultural protection. Mixtures of the compounds of the present invention with other herbicides can extend the spectrum of activity against additional weed species and suppress the growth of various resistant biotypes. Thus, the present invention also relates to compositions comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount), and can further comprise at least one surfactant, solid diluent, or liquid diluent. Other biologically active compounds or agents can be formulated in compositions that include at least one of a surfactant, a solid diluent, or a liquid diluent. With respect to the mixtures of the present invention, one or more other biologically active compounds or agents can be formulated with the compound of Formula 1 to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations can be combined together (e.g., in a spray tank) prior to application or alternatively applied sequentially.

[0334] Mixtures of the compounds of the invention with one or more of the following herbicides may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, bixlozone, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, Bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazon, benzobicyclon, benzofenap, bicyclopyrone, bifenox, viranaphos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxime, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butyrate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, clomethoxyfen, chloramphenicol ... Loramban, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clasifos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, chloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cyclo Roxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isooctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, dymron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetrin, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl,Diclosulam, difenzoquat methylsulfate, diflufenican, diflufenzopyr, dimefron, dimepiperate, dimesulfazate, dimethachlor, dimethametrin, dimethenamid, dimethenamid-P, dimethipine, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamide, diquat dibromide, dithiopyr, diuron, DNOC, endothall, EPTC, epirifenacil, esprocarb, ethalfluralin, ethametsulfuron-methyl, etiodin, ethofumesate, ethoxyfen, etoxane Cisulfuron, etobenzanide, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetosulam, flu Microlac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (sesquinate) sodium) and trimesium (also known as sulfosate) salts, halaxifen, halaxifen-methyl, halosulfuron-methyl, haloxyfop-ethotyl, haloxyfop-methyl, hexazinone, hydantocidin, imazametabunzu-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate,Ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium, and MCPA-sodium), esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB -ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mezosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium, and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, methoxyuron, metribuzin, metsulfuron-methyl, molinate, monolinone, naproxen Do, napropamide, napropamide-M, naptalam, nevron, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxulam, pentanochlor, pentoxazone, perfluidon, petoxamide, petoxamide, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretila Chlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolinate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, biributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan,Pyrithiobac, pyrithiobac-sodium, pyroxasulfone, piroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium salt, tebutam, tebuthiuron, tefuryltrione, tembotrione, Tepraloxydim, Terbacil, Terbumeton, Terbuthylazine, Terbutryn, Tetofurpyrolimet, Thenylchlor, Thiazopyr, Thiencarbazone, Thifensulfuron-methyl, Thiobencarb, Thiafenacil, Thiocarbazil, Tolpyralate, Topramezone, Tralkoxydim, Tri-Alert, Triafamone, Triasulfuron, Triaziflam, Tribenuron-methyl, Triclopyr, Triclopyr-butotyl, Triclopyr-triethylammonium, Tridiphane, Trietazine, Trifluro Xisulfuron, trifludimoxadine, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl) -3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (formerly known as methioxolin),4-(4-Fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid methyl ester, 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide, and 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides include those for Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar:Fries, Phytophthora palmivora (Butl.) Butl., and Puccinia thlaspeos Schub.

[0335] Preferred for better control of undesirable vegetation (e.g., reduced application rates due to increased efficacy, increased spectrum of weed control, or increased crop safety) or to prevent the development of resistant weeds are mixtures of the compounds of the present invention with herbicides selected from the group consisting of atrazine, azimsulfuron, S-beflubutamid, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, chloransulam-methyl, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, 2-[(2,5-dichlorophenyl)methyl]-4,4 -dimethyl-3-isoxazolidinone, ethametsulfuron-methyl, flumetoslam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,4H)-dione, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, metribuzin, metsulfuron-methyl, petoxamide, picloram, pyroxasulfone, quinclorac, rimsulfuron, S-metolachlor, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl, and tribenuron-methyl.

[0336] The compounds of the invention may also be used in combination with plant growth regulators such as aviglycin, N-(phenylmethyl)-1H-purin-6-amine, epocholeon, gibberellic acid, gibberellins A4 and A7, harpin proteins, mepiquat chloride, prohexadione calcium, prohydrojasmone, sodium nitrophenolate, and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.

[0337] General references for agricultural protectants (i.e., herbicides, herbicide safeners, insecticides, fungicides, nematicides, acaricides, and biological agents) include: The Pesticide Manual, 13th Edition, CDS Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2003, and The BioPesticide Manual, 2nd Edition, L.G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2001.

[0338] In embodiments in which one or more of these various mixing partners are used, the mixing partners are typically used in amounts comparable to those customarily used when the mixing partners are used alone. More specifically, in mixtures, the active ingredients are often applied at application rates between half and full of the application rate for the active ingredient alone as specified on the product label. These amounts are described, for example, in the following references: The Pesticide Manual and The BioPesticide Manual. The weight ratio of these various mixing partners (combined) to the compound of Formula 1 is typically between about 1:3000 and about 3000:1. Of note are weight ratios of about 1:300 to about 300:1 (e.g., ratios of about 1:30 to about 30:1). Those skilled in the art can easily determine by simple experimentation the biologically effective amount of the active ingredient required to achieve the desired spectrum of biological activity. It will be apparent that the inclusion of these additional components can broaden the spectrum of weeds controlled beyond that controlled by the compound of Formula 1 alone.

[0339] In certain cases, the compounds of the present invention may be combined with other biologically active (especially herbicidal) compounds or agents (i.e., active ingredients) to achieve greater than additive (i.e., enhanced) effects on weeds and / or less than additive (i.e., safer) results on crops or other desirable plants. Reducing the amount of active ingredient released into the environment while still ensuring effective pest control is always desirable. The ability to use greater amounts of active ingredient to achieve more effective weed control without excessive crop damage is also desirable. When the enhanced effect of a herbicidal mixture of active ingredients occurs on weeds at application rates that provide an agronomically satisfactory level of weed control, such combinations can be advantageous for reducing crop production costs and reducing environmental impact. If safeners of herbicidal active ingredients occur on crops, such combinations can be advantageous for reducing weed competition and enhancing crop protection.

[0340] Of note is the combination of the compound of the present invention with at least one other herbicidal active ingredient. Particularly noteworthy is a combination in which the other herbicidal active ingredient has a different site of action from the compound of the present invention. In some cases, a combination with at least one other herbicidal active ingredient having a similar control spectrum but a different site of action may be particularly advantageous for resistance management. Therefore, the composition of the present invention may further contain at least one additional herbicidal active ingredient (in a herbicidally effective amount) having a similar control spectrum but a different site of action.

[0341] The compounds of the invention can also be used in combination with herbicide safeners to increase safety in certain crops, such as, for example, allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, dymron, dichlormid, dicyclonone, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON). 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and 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 additional effective amount of a herbicide safener can be applied simultaneously with the compounds of the invention or as a seed treatment. Thus, an aspect of the invention relates to herbicidal mixtures comprising a compound of the invention and an antidotal effective amount of a herbicide safener. Seed treatments are particularly useful for selective weed control because they have limited antidotal effect on the crop.Thus, a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesirable vegetation in a crop, which comprises contacting a locus of the crop with a herbicidally effective amount of a compound of the present invention, wherein the seeds from which the crop grows are treated with an antidotal effective amount of a safener, which antidotal effective amount can be readily determined by one skilled in the art by simple experimentation.

[0342] The compounds of the present invention may also be mixed with: (1) polynucleotides, including but not limited to, DNA, RNA, and / or chemically modified nucleotides that affect the abundance of specific targets through, for example, downregulation, interference, suppression, or silencing of engineered transcripts to confer a herbicidal effect; or (2) polynucleotides, including but not limited to, DNA, RNA, and / or chemically modified nucleotides that affect the abundance of specific targets through, for example, downregulation, interference, suppression, or silencing of engineered transcripts to confer a safening effect.

[0343] Of note are compositions comprising (a herbicidally effective amount of) a compound of the present invention, (an effective amount of) at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one ingredient selected from the group consisting of surfactants, solid diluents, and liquid diluents.

[0344] Table A1 lists specific combinations of components (a) and (b) that illustrate the mixtures, compositions, and methods of the present invention. The compound number (compound number) in the component (a) column (i.e., Compound 1) is identified in Index Table A. The second column of Table A1 lists specific component (b) compounds (e.g., "2,4-D" in the first row). The third, fourth, and fifth columns of Table A1 list the weight ratio ranges at which component (a) compounds are typically applied to field-grown crops relative to component (b) (i.e., (a):(b)). Thus, for example, the first row of Table A1 specifically discloses that a combination of component (a) (i.e., Compound 1 in Index Table A) and 2,4-D is typically applied in a weight ratio between 1:384 and 6:1. The remaining rows of Table A1 are similarly organized.

[0345] [Table 49]

[0346] [Table 50]

[0347] [Table 51]

[0348] [Table 52]

[0349] [Table 53]

[0350] [Table 54]

[0351] [Table 55]

[0352] [Table 56]

[0353] Table A2 is structured the same as Table A1 above, except that the content under the "Component (a)" column heading is replaced with the respective component (a) column shown below. The compound numbers in the component (a) column are identified in Index Table A. Thus, for example, in Table A2, all content under the "Component (a)" column heading represents "Compound 2" (i.e., Compound 2 as identified in Index Table A), and the first row under the column heading in Table A2 specifically discloses a mixture of Compound 2 with 2,4-D. Tables A3-A60 are structured similarly.

[0354] [Table 57]

[0355] Preferred for better control of undesirable vegetation (e.g., reduced application rate due to increased efficacy, increased spectrum of weeds controlled, or increased crop safety) or prevention of the emergence of resistant weeds are mixtures of a compound of the invention with a herbicide selected from the group consisting of chlorimuron ethyl, nicosulfuron, mesotrione, thifensulfuron methyl, flupyrsulfuron methyl, tribenuron, pyroxasulfone, pinoxaden, tembotrione, pyroxsulam, metolachlor and S-metolachlor.

[0356] In one aspect, the group -CR in the compound of formula 1 3 R 14 OCOXR 4These compounds have been found to have improved herbicidal activity against specific weeds in specific crops, more favorable pharmacokinetic properties, or better toxicity profiles compared to compounds that do not contain this group (i.e., the group is replaced by H or certain other groups). This surprising improvement is due to the presence of the group -CR. 3 R 14 OCOXR 4 is not a simple cleavable group. Improved pharmacokinetic properties or better tox profiles can be assessed by the protocols described below.

[0357] Acute toxicity test in rats An acute oral toxicity study is conducted in rats. Two groups of rats are prepared for administration of the test substance. Group 1, consisting of two rats, is scheduled to receive 300 mg / kg body weight, and Group 2, consisting of one rat, is scheduled to receive 50 mg / kg body weight. The second group of rats is dosed depending on the findings from Group 1. Animals in each group are dosed once and observed for 14 days. Animals are observed twice daily for mortality, morbidity, and general health. Clinical observations (skin and coat characteristics, eyes and mucous membranes, respiration, circulation, autonomic and central nervous systems, body movement, and behavioral patterns) are monitored pre-dose, on study day 8, and then on study day 15. Unscheduled observations are also recorded during the study. Body weights are measured pre-dose, on study day 8, and on study day 15. Unscheduled terminations are recorded and animals weighed accordingly.

[0358] Toxicokinetics and oral toxicity screening in rats after single dose administration Three rats are administered the test substance at two different dose levels: 25 mg / kg body weight and 300 mg / kg body weight. Animals are observed for 7 days. Body weights are measured the day before dosing, immediately before dosing, and daily thereafter. Mortality and morbidity are checked twice daily. Blood is collected from animals at 0.5, 1, 2, 4, 8, 12, 24, 48, 72, 96, 120, 144, 168 hours, and at sacrifice. After dosing, approximately 0.2 mL of blood is collected into tubes containing EDTA at intervals outlined in the study design and kept on ice until processed into plasma. Processing occurs within approximately 2 hours of collection. To separate plasma from red blood cells, whole blood is centrifuged at approximately 2500 rpm for 5 minutes at 4°C. Plasma is stored frozen (≦10°C) until analysis. At sacrifice, blood is collected before being processed into plasma as described above. 0.5 g of perirenal fat is collected from the animals on the day of sacrifice and stored at ≤10°C until analysis. Plasma and fat are analyzed by ultra-performance liquid chromatography with tandem mass spectrometry detection (LC-MS / MS) to determine the concentration of the test substance. Plasma concentration time course data from each animal are analyzed to determine pharmacokinetic parameters, including terminal half-life (T1 / 2, h), area under the curve (AUC, h x ng / mL), peak concentration (Cmax, ng / mL), and time to peak concentration (Tmax, h). These pharmacokinetic parameters, along with dose-normalized values ​​for AUC and Cmax, are calculated by non-compartmental analysis using commercially available software programs. Additionally, the fat:plasma concentration ratio is determined at the time of terminal sacrifice.

[0359] Plasma protein binding Tests are performed in rat plasma and recovered with K2EDTA. An equilibrium dialysis device is used for all experiments. Stock solutions of test and control compounds are first prepared in dimethyl sulfoxide (DMSO). Aliquots of DMSO solution are administered to 1.0 mL of plasma at a dose concentration of 5 μM for the test article and 10 μM for the co-administered control compound. Plasma (300 μL) containing the test article and control compound is loaded into two wells of a 96-well dialysis plate. Blank phosphate-buffered saline (500 μL) is added to each corresponding receiver chamber. The device is then placed in a sealed heating rocker preheated to 37 °C and incubated for 4 hours, after which both sides are sampled. Aliquots (50 μL for the donor and 200 μL for the receiver) are removed from the chambers and placed in a 96-well plate. Plasma (50 μL) is added to the well containing the receiver sample, and 200 μL of PBS is added to the well containing the donor sample. Two volumes of acetonitrile are added to each well, the plate is mixed, and then centrifuged at 3,000 rpm for 10 minutes. An aliquot of the supernatant is removed, diluted 1:1 with water, and analyzed by LC-MS / MS. Protein binding values ​​are calculated as follows: % binding = [(PARR in donor - PARR in receiver) / (PARR in donor)] x 100; PARR = peak area response ratio to the internal standard, including the applicable dilution factor.

[0360] Blood partitioning into plasma The test is performed on rat whole blood and collected with K2EDTA. Blood is kept on ice before the experiment. Hematocrit (ratio of red blood cell volume to whole blood volume) is measured by centrifuging whole blood for 5 minutes using a microhematocrit capillary (n=3). Control plasma is obtained from a portion of the whole blood by centrifugation at 1,000 g for 10 minutes. The whole blood and control plasma are adjusted to pH 7.4 and then warmed in a water bath at 37°C for 10 minutes. Test articles and control compounds are added to aliquots of whole blood and control plasma. The final concentrations in the incubation are 5 μM for the test articles and 5 μM for the control compounds. All samples are then incubated in a shaking water bath at 37°C. The total organic solvent content during the incubation was less than 1.0%. After 60 minutes of incubation (n=2), the incubated whole blood is removed from the water bath and the plasma is separated by centrifugation at 1,000 g for 10 minutes. An aliquot of control plasma is also removed. All samples are treated with 3 volumes of ice-cold acetonitrile containing an internal standard. After removal of plasma proteins by centrifugation at 1,640 g (3,000 rpm) at 4°C for 10 minutes, the supernatant is diluted with water and analyzed by LC-MS / MS.

[0361] RBC to plasma partitioning (KRBC / P) and whole blood to plasma partitioning (KWB / P) are calculated as follows: KRBC / P = (1 / H) * (CCP / CP - 1) + 1 KWB / P = CCP / CP; H = hematocrit CCP = control plasma response rate CP = plasma response rate.

[0362] Stability in hepatocytes Frozen rat cryopreserved hepatocytes were provided. The hepatocytes were thawed and prepared according to the supplier's instructions, pooled in a buffer solution (pH 7.4), and kept on ice prior to the experiment. The hepatocyte suspension was equilibrated in a shaking water bath at 37°C for 3 minutes, and then the reaction was initiated by adding the test compound to the hepatocyte suspension (1.0 x 106 cells / mL) at a final test compound concentration of 1 μM. The final DMSO content in the incubation mixture was ≦0.1%. The reaction mixture was incubated in a shaking water bath at 37°C. Positive control compounds A (1 μM) and B (100 μM) were run in parallel to confirm hepatocyte activity. Aliquots of the test compound were removed at 0, 5, 15, 30, 60, 90, 120, and 240 minutes (n=1). Aliquots of A were removed at 0, 5, 15, 30, 60, and 120 minutes (n=1). Aliquots of control compound B are removed at 0 and 15 minutes (n=1). Experiments are also performed simultaneously in assay buffer without hepatocytes. Samples from these experiments are collected at 0, 120, and 240 minutes. The reaction is immediately terminated by adding 3 volumes of ice-cold acetonitrile containing the internal standard. The samples are then mixed and centrifuged to precipitate the protein. An aliquot of the supernatant is then diluted with water. Calibration standards for analysis of metabolites of control compound B are prepared in a matched matrix. Test article and control compound A samples are analyzed without calibration standards. All samples are analyzed by LC-MS / MS. The peak area response ratio (PARR) versus the internal standard is compared to the PARR at time 0 to determine the fraction remaining at each time point. Half-life and clearance values ​​are calculated using commercially available graphing software and fit to a single-phase exponential decay equation.

[0363] The following tests demonstrate the control efficacy of the compounds of the present invention against specific weeds. However, the weed control achieved by these compounds is not limited to these species. See Index Table A for compound descriptions. The following abbreviations are used in the Index Table below: "Cmpd.No." stands for "Compound Number," "Ex." stands for "Example," followed by a number indicating in which example the compound was prepared. 1H NMR spectra are reported in ppm downfield from tetramethylsilane in CDCl3 solution unless otherwise indicated, where i-Pr means isopropyl, t-Bu means tertiary butyl, s means singlet, d means doublet, dd means doublet of doublet, ddd means doublet of doublet of doublet, t means triplet, dt means doublet of triplet, td means triplet of doublet, q means quintet, and m means multiplet. Indicator table A [ka] R 3 is H;

[0364] [Table 58]

[0365] Indicator table B [ka]

[0366] [Table 59]

[0367] Indicator table C [ka]

[0368] [Table 60]

[0369] [Table 61]

[0370] Biological Examples of the Invention Test A Barnyardgrass (Echinochloa crus-galli), black foxtail (Alopecurus myosuroides), corn (Zea mays), foxtail (giant foxtail), green foxtail (Setaria faberi), goosegrass (Eleusine indica), kochia (Bassia scoparia), oats (Avena fatua), pigweed (palmer), redroot pigweed (Amaranthus palmeri), common ragweed (Ambrosia artemisiifolia), Italian ryegrass (Lolium multiflorum), and soybean (Glycine max). Seeds of plant species selected from (L. max) were planted in a blend of loam soil and sand and pre-emergence treated with a directional soil spray using test chemicals formulated in a non-phytotoxic solvent mixture containing a surfactant.

[0371] Simultaneously, these crop and weed species, as well as plants selected from wheat (Triticum aestivum), catchweed bedstraw (Galium aparine), and sagebrush (Erigeron canadensis), were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of identically formulated test chemicals. Plant heights ranged from 2 cm to 10 cm and were at the one- to two-leaf stage for postemergence treatment. Treated plants and untreated controls were maintained in the greenhouse for 10 days, after which all treated plants were compared to untreated controls and visually evaluated for damage. Plant response ratings, summarized in Table A, are based on a scale of 0 to 100, where 0 is no effect and 100 is complete control. A dash (-) response indicates no test result.

[0372] [Table 62]

[0373] [Table 63]

[0374] [Table 64]

[0375] [Table 65]

[0376] [Table 66]

[0377] [Table 67]

[0378] [Table 68]

[0379] [Table 69]

[0380] Test B Flooded paddy test plant species selected from barnyardgrass (Echinochloa crus-galli), American corngrass (Heteranthera limosa), rice (Oryza sativa), and small-flower umbrella sedge (Cyperus difformis) were grown to the two-leaf stage for testing. At the time of treatment, test pots were flooded to 3 cm above the soil surface and treated by applying test compounds directly to the paddy water, then maintained at that water depth for the duration of the test. Treated plants and controls were held in the greenhouse for 10-14 days, after which all species were visually evaluated compared to the control. Plant response, summarized in Table B, was rated on a 0-100 scale, with 0 representing no effect and 100 representing complete control. A dash (-) response indicates no test result.

[0381] [Table 70]

Claims

1. Compounds of formula 1, all stereoisomers, N-oxides, and salts thereof, 【Chemistry 1】 During the ceremony, R 1 is H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, benzyl or phenyl (the ring in the benzyl or phenyl group is not substituted with halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; R 2 is H, halogen, cyano, formyl, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 2 ~C 4 alkylcarbonyl, C 2 ~C 7 Alkylcarbonyloxy, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Alkylamino, C 2 ~C 8 Dialkylamino, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, C 1 ~C 5 Alkylthio or C 2 ~C 3 Alkoxycarbonyl; or halogen, C 1 ~C 4 Alkyl or C 1 ~C 4 phenyl optionally substituted with haloalkyl; R 3 is H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 alkoxy; or benzyl or phenyl (wherein the ring in the benzyl or phenyl group is not substituted with halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; R 4 is H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, (CH 2 CH 2 O) tR 5 or benzyl or phenyl (the ring in the benzyl or phenyl group may be selected from the group consisting of halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; R 5 is H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 alkoxy; or benzyl or phenyl (the ring in the benzyl or phenyl group is not subject to halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; t is an integer from 1 to 10; X is a direct bond, O, S or NR 6 and R 6 is H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 alkoxy; or benzyl or phenyl (the ring in the benzyl or phenyl group is not subject to halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 or a 5- or 6-membered saturated or partially saturated heterocyclic ring containing carbon and up to one O and up to one S ring member, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 haloalkoxy); or R 4 and R 6 can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing carbon atoms and optionally 1 to 3 oxygen, sulfur, or nitrogen atoms as ring members, wherein up to two carbon atom ring members are independently selected from C(=O) and C(=S), and said sulfur atom ring members are S, S(O) or S(O) 2 wherein the ring is selected from halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; A is, 【Chemistry 2】 is selected from X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 are each independently N or CR 7 where X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 and X 10 of which no more than four are N; X 11 is O, S or NR 9 or X 11 is -C(R 10 ) = C(R 11 )-, and in Formula 1, R 10 The carbon atom bonded to R 13 is also bonded to a carbon atom bonded to R 11 is also bonded to a phenyl ring moiety; Y is O, S or NR 8 and Y 1 is O, S, NR 8 or CR 7a R 7b and Each R 7 are independently H, halogen, cyano, nitro, C 1 ~C 5 Alkyl, C 2 ~C 5 Alkenyl, C 2 ~C 5 Alkynyl, C 3 ~C 5 Cycloalkyl, C 4 ~C 5 Cycloalkylalkyl, C 1 ~C 5 Haloalkyl, C 3 ~C 5 Haloalkenyl, C 3 ~C 5 Haloalkynyl, C 2 ~C 5 Alkoxyalkyl, C 1 ~C 5 Alkoxy, C 1 ~C 5 Haloalkoxy, C 1 ~C 5 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 5 Haloalkylthio or C 2 ~C 5 is alkoxycarbonyl; R 7a is H, halogen, -CN, nitro, C 1 ~C 5 Alkyl, C 2 ~C 5 Alkenyl, C 2 ~C 5 Alkynyl, C 3 ~C 5 Cycloalkyl, C 4 ~C 5 Cycloalkylalkyl, C 1 ~C 5 Haloalkyl, C 3 ~C 5 Haloalkenyl, C 3 ~C 5 Haloalkynyl, C 2 ~C 5 Alkoxyalkyl, C 1 ~C 5 Alkoxy, C 1 ~C 5 Haloalkoxy, C 1 ~C 5 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 5 Haloalkylthio or C 2 ~C 5 is alkoxycarbonyl; R 7b is H, halogen, -CN, nitro, C 1 ~C 5 Alkyl, C 2 ~C 5 Alkenyl, C 2 ~C 5 Alkynyl, C 3 ~C 5 Cycloalkyl, C 4 ~C 5 Cycloalkylalkyl, C 1 ~C 5 Haloalkyl, C 3 ~C 5 Haloalkenyl, C 3 ~C 5 Haloalkynyl, C 2 ~C 5 Alkoxyalkyl, C 1 ~C 5 Alkoxy, C 1 ~C 5 Haloalkoxy, C 1 ~C 5 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 5 Haloalkylthio or C 2 ~C 5 alkoxycarbonyl; or R 7a and R 7b is combined with =O or R 7a and R 7b together with the carbon atoms to which they are attached form an optionally substituted 3- to 7-membered carbocyclic ring; R 8 is H, C 1 ~C 3 Alkyl or C 1 ~C 3 haloalkyl; R 9 is H, C 1 ~C 3 Alkyl or C 1 ~C 3 haloalkyl; R 10 and R 11 are independently H, halogen, nitro, —CN, C 1 ~C 5 Alkyl, C 2 ~C 5 Alkenyl, C 2 ~C 5 Alkynyl, C 3 ~C 5 Cycloalkyl, C 4 ~C 5 Cycloalkylalkyl, C 1 ~C 5 Haloalkyl, C 3 ~C 5 Haloalkenyl, C 3 ~C 5 Haloalkynyl, C 2 ~C 5 Alkoxyalkyl, C 1 ~C 5 Alkoxy, C 1 ~C 5 Haloalkoxy, C 1 ~C 5 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 5 Haloalkylthio or C 2 ~C 5 is alkoxycarbonyl; Each R 12 are independently halogen, —CN, nitro, C 1 ~C 5 Alkyl, C 2 ~C 5 Alkenyl, C 2 ~C 5 Alkynyl, C 3 ~C 5 Cycloalkyl, C 4 ~C 5 Cycloalkylalkyl, C 1 ~C 5 Haloalkyl, C 3 ~C 5 Haloalkenyl, C 3 ~C 5 Haloalkynyl, C 2 ~C 5 Alkoxyalkyl, C 1 ~C 5 Alkoxy, C 1 ~C 5 Haloalkoxy, C 1 ~C 5 Alkylthio, C 1 ~C 5 Haloalkylthio or C 2 ~C 5 is alkoxycarbonyl; R 13 is H, halogen, nitro, -CN, C 1 ~C 5 Alkyl, C 2 ~C 5 Alkenyl, C 2 ~C 5 Alkynyl, C 3 ~C 5 Cycloalkyl, C 4 ~C 5 Cycloalkylalkyl, C 1 ~C 5 Haloalkyl, C 3 ~C 5 Haloalkenyl, C 3 ~C 5 Haloalkynyl, C 2 ~C 5 Alkoxyalkyl, C 1 ~C 5 Alkoxy, C 1 ~C 5 Haloalkoxy, C 1 ~C 5 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 5 Haloalkylthio or C 2 ~C 5 is alkoxycarbonyl; R 14 is H; n is 0, 1, 2, 3 or 4; Compounds of formula 1, all stereoisomers, N-oxides, and salts thereof.

2. A is A-11; R 1 But H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Arco Carbonyl alkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 alkoxy; or benzyl or phenyl (the ring in the benzyl or phenyl group is not subject to halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; R 2 H, halogen, cyano, formyl, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 2 ~C 4 Alkylcarbonyl, C 2 ~C 7 Alkylcarbonyloxy, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Alkylamino, C 2 ~C 8 Dialkylamino, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, C 1 ~C 5 Alkylthio or C 2 ~C 3 is alkoxycarbonyl; R 3 But H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 alkoxy; or benzyl or phenyl (the ring in the benzyl or phenyl group is not subject to halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; R 4 is H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 C4 to C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 cycloalkyl, —C 1 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, (CH 2 CH 2 O) tR 5 or benzyl or phenyl (the ring in the benzyl or phenyl group may be selected from the group consisting of halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; Each R 12 are independently halogen, —CN, C 1 ~C 3 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 3 ~C 4 Cycloalkyl, C 1 ~C 3 Haloalkyl, C 1 ~C 3 Alkoxy, C 1 ~C 2 Haloalkoxy, C 1 ~C 2 Alkylthio or C 1 ~C 2 haloalkylthio; R 13 is halogen, -CN, C 1 ~C 3 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 3 ~C 4 Cycloalkyl, C 1 ~C 3 Haloalkyl, C 1 ~C 3 Alkoxy, C 1 ~C 2 Haloalkoxy, C 1 ~C 2 Alkylthio or C 1 ~C 2 Haloalkyl O The compound of claim 1.

3. R 1 But C 1 ~C 4 Alkyl, C 3 ~C 4 Alkenyl, C 3 ~C 4 Alkynyl, C 3 ~C 4 Cycloalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 3 Haloalkyl or C 2 ~C 4 Alkoxya It is Lukil; R 2 H, halogen, -CN, C 1 ~C 4 Alkyl, C 3 ~C 5 Cycloalkyl, C 1 ~C 3 Haloalkyl, C 2 ~C 4 Alkoxyalkyl or C 1 ~C 3 is alkoxy; R 3 But H, C 1 ~C 4 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl or C 1 ~C 7 is alkoxy; R 4 But H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl or C 1 ~C 7 is alkoxy; R 12 are independently halogen, —CN, methyl, ethyl, methoxy, or ethoxy; R 13 is halogen, -CN, methyl, ethyl, -CH=CH 2 , —C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy; The compound of claim 2.

4. R 1 But C 1 ~C 3 Alkyl, allyl, propargyl, CH 2 CH 2 C.N., C. 1 ~C 2 haloalkyl or 2-methoxyethyl; R 2 H, halogen, C 1 ~C 3 Alkyl, cyclopropyl, C 1 ~C 2 haloalkyl, methoxy, or ethoxy; R 3 But H, C 1 ~C 4 Alkyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 cycloalkylalkyl, or C 1 ~C 7 is alkoxy; R 4 But H, C 1 ~C 4 Alkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl or C 1 ~C 7 is alkoxy; Each R 12 is independently F, Cl, Br, methyl, ethyl, or methoxy; n is 0, 1 or 2; The compound of claim 3.

5. R 1 is methyl, ethyl, n-propyl, or 2-methoxyethyl; R 2 is H, F, Cl, methyl, ethyl, n-propyl, CF 3 or methoxy; R 3 is H or methyl; R 4 But H, C 1 ~C 4 Alkyl, C 4 ~C 7 Cycloalkylalkyl or C 1 ~C 7 is alkoxy; X 11 But -C(R 10 ) = C(R 11 ) - and Independently, R 10 and R 11 is H, halogen or C 1 ~C 2 is alkyl, The compound of claim 4.

6. R 1 is methyl; R 2 is Me or Cl; R 3 is H; R 4 is H, methyl, ethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy or ethoxy; R 10 is H and R 11 is H or R 10 is H and R 11 is CH 3 is or R 6 is CH 3 and R 7 is H, The compound of claim 5.

7. R 1 is methyl, ethyl, n-propyl, or 2-methoxyethyl; R 2 is H, F, Cl, methyl, ethyl, n-propyl, CF 3 or methoxy; R 3 is H or methyl; R 4 But H, C 1 ~C 4 Alkyl, C 4 ~C 7 cycloalkylalkyl, or C 1 ~C 7 is alkoxy; X 11 is O, The compound of claim 4.

8. R 1 is methyl, ethyl, n-propyl, or 2-methoxyethyl; R 2 is H, F, Cl, methyl, ethyl, n-propyl, CF 3 or methoxy; R 3 is H or methyl; R 4 But H, C 1 ~C 4 Alkyl, C 4 ~C 7 cycloalkylalkyl, or C 1 ~C 7 is alkoxy; X 11 is S, The compound of claim 4.

9. X is a direct bond or O; The compound of claim 4.

10. A is selected from A-1, A-4 and A-6; R 1 But H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 alkoxy; or benzyl or phenyl (the ring in the benzyl or phenyl group is not subject to halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; R 2 H, halogen, cyano, formyl, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 2 ~C 4 Alkylcarbonyl, C 2 ~C 7 Alkylcarbonyloxy, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Alkylamino, C 2 ~C 8 Dialkylamino, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 1 ~C 7 Alkoxy, C 1 ~C 5 Alkylthio or C 2 ~C 3 is alkoxycarbonyl; R 3 But H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 alkoxy; or benzyl or phenyl (the ring in the benzyl or phenyl group is not subject to halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy; R 4 But H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C4-C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C4-C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~ C 7 Haloalkyl, C 3 ~C 7 Haloalkenyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 Alkoxy, (CH 2 CH 2 O) tR 5 or benzyl or phenyl (the ring in the benzyl or phenyl group is not optionally substituted with halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy and C 1 ~C 4 and optionally substituted with at least one substituent independently selected from the group consisting of haloalkoxy. The compound of claim 1.

11. A is A-1; R 1 But H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 4 Nitroalkyl, C 2 ~C 7 Haloalkoxyalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl, C 3 ~C 7 Alkylthioalkyl, C 1 ~C 7 alkoxy or benzyl; R 2 H, halogen, -CN, C 1 ~C 4 Alkyl, C 3 ~C 5 Cycloalkyl, C 1 ~C 3 Haloalkyl, C 2 ~C 4 Alkoxyalkyl or C 1 ~C 3 is alkoxy; R 3 But H, C 1 ~C 4 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 7 Haloalkyl, C 2 ~C 7 Alkoxyalkyl or C 1 ~C 7 is alkoxy; R 4 But H, C 1 ~C 7 Alkyl, C 3 ~C 8 Alkylcarbonylalkyl, C 3 ~C 8 Alkoxycarbonylalkyl, C 4 ~C 7 Alkylcycloalkyl, C 3 ~C 7 Alkenyl, C 3 ~C 7 Alkynyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 Cycloalkylalkyl or C 1 ~C 7 is alkoxy; Each X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 and X 9 But, CR 7 and Each R 7 are independently H, halogen, C 1 ~C 3 Alkyl, C 3 ~C 4 Cycloalkyl, C 1 ~C 3 Haloalkyl or C 1 ~C 3 is alkoxy; X is a direct bond or O; The compound of claim 10.

12. R 1 But C 1 ~C 4 Alkyl, C 3 ~C 4 Alkenyl, C 3 ~C 4 Alkynyl, C 3 ~C 4 Cycloalkyl, C 2 ~C 3 Cyanoalkyl, C 1 ~C 3 Haloalkyl or C 2 ~C 4 is alkoxyalkyl; R 2 H, halogen, C 1 ~C 3 Alkyl, cyclopropyl, C 1 ~C 2 haloalkyl, methoxy, or ethoxy; R 3 But H, C 1 ~C 4 Alkyl, C 3 ~C 7 Cycloalkyl, C 4 ~C 7 cycloalkylalkyl, or C 1 ~C 7 is alkoxy; Each R 7 are independently H, halogen, C 1 ~C 2 Alkyl, cyclopropyl or C 1 ~C 2 haloalkyl, The compound of claim 11.

13. R 1 is methyl, ethyl, n-propyl, or 2-methoxyethyl; R 2 is H, F, Cl, methyl, ethyl, n-propyl, CF 3 or methoxy; Each R 7 are independently H, halogen, methyl, ethyl or CF 3 That is, The compound of claim 12.

14. 5-[(acetyloxy)methoxy]-6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-2-methyl-3(2H)-pyridazinone; 5-[(acetyloxy)methoxy]-4-(2-bromo-5-fluorobenzo[b]thien-3-yl)-2,6-dimethyl-3(2H)-pyridazinone; [[5-(2-fluoro-7-methyl-9-anthracenyl)-1,6-dihydro-1,3-dimethyl-6-oxo-4-pyridazinyl]oxy]methyl methyl carbonate; 5-[(acetyloxy)methoxy]-6-chloro-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2H)-pyridazinone; and 5-[(acetyloxy)methoxy]-4-(2-fluoro-7-methyl-9-anthracenyl)-2,6-dimethyl-3(2H)-pyridazinone 2. The compound of claim 1 selected from the group consisting of:

15. 10. A herbicide composition comprising the compound of claim 1 and at least one component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent.

16. 10. A herbicide composition comprising the compound of claim 1, other herbicides and herbicide safeners, and at least one additional active ingredient selected from the group consisting of surfactants, solid diluents, and liquid diluents.

17. 1. A herbicidal mixture comprising: (a) the compound of claim 1; and (b) the following: (b1) a photosystem II inhibitor, (b2) an acetohydroxyacid synthase (AHAS) inhibitor, (b3) an acetyl-CoA carboxylase (ACCase) inhibitor, (b4) an auxin mimetic, (b5) a 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitor, (b6) a photosystem I electron diverter, (b7) a protoporphyrinogen oxidase (PPO) inhibitor, (b8) a glutamine synthetase (GS) inhibitor, (b9) a very long chain fatty acid (VLCFA) elongase inhibitor, (b10) an auxin transport inhibitor, (b11) a phytoene desaturase (PDS) inhibitor, (b12) a 4-hydroxybenzoate (4-hydroxybenzoate) synthase ... (b13) a hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor, (b14) a cellulose biosynthesis inhibitor, (b15) other herbicides (including mitotic disruptors, organic arsenic compounds, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanide, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, and biributicarb), (b16) a herbicide safener, and at least one further active ingredient selected from salts of the compounds of (b1) to (b16).

18. 10. A method for controlling the growth of undesirable vegetation comprising contacting said vegetation or its environment with a herbicidally effective amount of a compound of claim 1.

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