Herbicide derivative

Abstract

A compound of formula (I) wherein the substituents are as defined in claim 1. The present invention further relates to a herbicidal composition comprising a compound of formula (I), and to the use of a compound of formula (I) for controlling weeds in crops of particularly useful plants. [Chemical 1] JPEG2025519205000033.jpg35161

Description

Technical Field

[0001] The present invention relates to herbicidal pyridone derivatives, for example, as active ingredients having herbicidal activity. The present invention also relates to pesticidal compositions containing at least one pyridone derivative, processes for preparing these compounds, and the use of pyridone derivatives or compositions in the control of weeds in crops of particularly useful plants in agriculture or horticulture.

Background Art

[0002] EP 0239391, EP 0127313, EP 0040082, and GB 2182931 describe pyridone derivatives as herbicides.

Summary of the Invention

Means for Solving the Problems

[0003] According to the present invention, formula (1):

Chemical Formula

[0004] Surprisingly, the novel compounds of formula (I) have been found to have a very advantageous level of herbicidal activity for practical purposes.

[0005] According to a second aspect of the present invention, there is provided an agrochemical composition comprising a herbicidally effective amount of a compound of formula (I) according to the present invention. Such an agricultural composition may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0006] According to a third aspect of the present invention, there is provided a method of controlling weeds in a habitat, the method comprising applying to the habitat a composition comprising a weed controlling amount of a compound of formula (I).

[0007] According to a fourth aspect of the present invention, there is provided the use of a compound of formula (I) as a herbicide.

DETAILED DESCRIPTION OF THE INVENTION

[0008] When a substituent is described as "optionally substituted", this means one or more equivalent or different substituents, for example 1, 2 or 3 R 9It means that it may or may not have a substituent. For example, C1-C6 alkyl substituted by 1, 2 or 3 halogens is not particularly limited, and examples thereof may include -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, C1-C6 alkoxy substituted by 1, 2 or 3 halogens is not particularly limited thereto, and examples thereof may include CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O- or CH3CF2O- groups.

[0009] As used herein, the term "cyano" means a -CN group.

[0010] As used herein, the term "hydroxy" or "hydroxyl" refers to a -OH group.

[0011] As used herein, the term "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo).

[0012] As used herein, the term "nitro" means a -NO2 group.

[0013] As used herein, the term "formyl" means a -C(O)H group.

[0014] As used herein, the term "acetyl" means a -C(O)CH3 group.

[0015] As used herein, the term "C1-C6 alkyl" refers to a straight or branched hydrocarbon chain group consisting only of carbon and hydrogen atoms, containing no unsaturation, having 1-6 carbon atoms, and attached to the remainder of the molecule by a single bond. "C1-C4 alkyl" and "C1-C3 alkyl" should be interpreted similarly. Examples of C1-C6 alkyl include, but are not limited to, methyl, ethyl, n-propyl, and its isomers, such as isopropyl. A "C1-C6 alkylene" group refers to the corresponding definition of C1-C6 alkyl, except that such group is attached to the remainder of the molecule by two single bonds. The term "C1-C2 alkylene" should be interpreted similarly. Examples of C1-C6 alkylene include, but are not limited to, -CH2-, -CH2CH2-, and -(CH2)3-.

[0016] As used herein, the term "C1-C6 haloalkyl" refers to a C1-C6 alkyl group, generally as defined above, substituted with one or more of the same or different halogen atoms. The terms "C1-C4 haloalkyl" and "C1-C3 haloalkyl" should be interpreted similarly. Examples of C1-C6 haloalkyl include, but are not limited to, trifluoromethyl.

[0017] As used herein, the term "C1-C6 alkoxy" refers to R a is generally a C1-C6 alkyl group as defined above; a The terms "C1-C4 alkoxy" and "C1-C3 alkoxy" should be interpreted similarly. Examples of C1-C6 alkoxy include, but are not limited to, methoxy, ethoxy, 1-methylethoxy (isopropoxy), and propoxy.

[0018] As used herein, the term "C1-C6 haloalkoxy" refers to a C1-C6 alkoxy group as generally defined above, substituted with one or more identical or different halogen atoms. The terms "C1-C4 haloalkoxy" and "C1-C3 haloalkoxy" should be interpreted in the same manner. Examples of C1-C6 haloalkoxy include, but are not limited to, trifluoromethoxy.

[0019] As used herein, the term "cyano C1-C6 alkoxy" refers to a C1-C6 alkoxy group substituted with one or more cyano groups, as generally defined above. The terms "cyano C1-C4 alkoxy" and "cyano C1-C3 alkoxy" should be interpreted in the same manner. Examples of cyano C1-C6 alkoxy include, but are not limited to, cyanoethoxy.

[0020] As used herein, the term "C2-C6 alkenyl" refers to a straight-chain or branched-chain hydrocarbon chain group composed of only carbon and hydrogen atoms, containing at least one double bond that can be in the (E)- or (Z)-configuration and attached to the remainder of the molecule by a single bond, having 2 to 6 carbon atoms. The term "C2-C3 alkenyl" should be interpreted in the same manner. Examples of C2-C6 alkenyl include, but are not limited to, ethenyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), buta-1-enyl.

[0021] As used herein, the term "C2-C6 alkynyl" refers to a straight-chain or branched-chain hydrocarbon chain group composed of only carbon and hydrogen atoms, containing at least one triple bond, having 2 to 6 carbon atoms, and attached to the remainder of the molecule by a single bond. The term "C2-C3 alkynyl" should be interpreted in the same manner. Examples of C2-C6 alkynyl include, but are not limited to, ethynyl, prop-1-ynyl, buta-1-ynyl.

[0022] As used herein, the term "C2-C6 alkenyloxy" refers to a straight-chain or branched-chain hydrocarbon radical group consisting of only carbon and hydrogen atoms, containing at least one double bond that can be in the (E)- or (Z)-configuration, and having 2 to 6 carbon atoms bonded to the remainder of the molecule by an oxygen linker.

[0023] As used herein, the term "C1-C6 alkoxy C1-C6 alkyl" means that R b is generally a C1-C6 alkyl group as defined above, and R a is generally a C1-C6 alkylene group as defined above, and refers to a group of the formula R b OR a -. The term "C1-C4 alkoxy C1-C4 alkyl" should be interpreted in the same way.

[0024] As used herein, the term "C1-C6 alkoxy C1-C6 alkoxy" means that R a and R b are both generally C1-C6 alkylene groups as defined above, and refers to a group of the formula R b OR a O-. The term "C1-C4 alkoxy C1-C4 alkoxy" should be interpreted in the same way.

[0025] As used herein, the term "C1-C6 alkoxycarbonyl C1-C6 alkoxy" means that R a and R b are both generally C1-C6 alkylene groups as defined above, and refers to a group of the formula R b OC(O)R a O-.

[0026] As used herein, the term "C3-C6 cycloalkyl" refers to a monocyclic saturated ring system and a group containing 3 to 6 carbon atoms. The terms "C3-C5 cycloalkyl" and "C3-C4 cycloalkyl" should be interpreted in the same manner. Examples of C3-C6 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0027] As used herein, the term "C3-C6 cycloalkylaminocarbonyl" refers to a C3-C6 cycloalkyl ring attached to the remainder of the molecule via an -NHC(O)- linker.

[0028] As used herein, the term "benzyloxy" refers to a benzyl ring attached to the remainder of the molecule via an oxygen atom.

[0029] Unless otherwise indicated, as used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring group containing 1, 2, 3, or 4 heteroatoms individually selected from nitrogen, oxygen, and sulfur. In some instances, the heteroaryl moiety may be attached to the remainder of the molecule by a nitrogen atom in the heteroaryl ring. In other cases, the heteroaryl moiety may be attached to the remainder of the molecule by a carbon atom in the heteroaryl ring. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl.

[0030] As used herein, the term "heterocyclyl" refers to a stable 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms, where the heteroatoms are individually selected from nitrogen, oxygen and sulfur. The heterocyclyl group may be attached to the remainder of the molecule via a carbon atom or a heteroatom. Examples of heterocyclyl include, but are not limited to, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuryl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolanyl, dithiolanyl and thiazolidinyl.

[0031] As used herein, the term "C1-C6 alkylcarbonyl" means a group of the formula -C(O)R a wherein R is a C1-C6 alkyl group as generally defined above. Examples of C1-C6 alkylcarbonyl include, but are not limited to, acetyl. a

[0032] As used herein, the term "C1-C6 alkoxycarbonyl" means a group of the formula -C(O)OR a wherein R is a C1-C6 alkyl group as generally defined above. a

[0033] As used herein, the term "C1-C6 alkylamino" means a group of the formula R a NH- wherein R is a C1-C6 alkyl group as generally defined above. a

[0034] As used herein, the term "C1-C6 alkylaminocarbonyl" means a group of the formula -C(O)NHR a wherein R is a C1-C6 alkyl group as generally defined above. a

[0035] As used herein, the term "C1-C6 alkylcarbonylamino" generally refers to a group of the formula R a wherein R a is a C1-C6 alkyl group and C(O)NH-.

[0036] As used herein, the term "C1-C6 alkoxy C1-C6 alkylaminocarbonyl" generally refers to a group of the formula R a wherein R a is a C1-C6 alkyl group and R a is a C1-C6 alkylene group and OR b NHC(O)-.

[0037] As used herein, the term "C1-C6 alkoxy C1-C6 alkylcarbonylamino" generally refers to a group of the formula R a wherein R a is a C1-C6 alkyl group and R a is a C1-C6 alkylene group and OR b C(O)NH-.

[0038] As used herein, the term "C2-C6 alkenylcarbonylamino" generally refers to a group of the formula R a wherein R a is a C1-C6 alkylene group and OC(O)NH-.

[0039] As used herein, the term "N,N-di(C1-C4 alkyl)amino" generally refers to a group of the formula (R a )(R b )NH- wherein each R a and R b is independently a C1-C4 alkyl group.

[0040] As used herein, the term "N,N-di(C1-C4 alkyl)aminocarbonyl" refers to R a and Rb each represents an individually generally C1-C4 alkyl group as defined above of the formula -C(O)N(R a )(R b ). The term "N,N-di(C1-C3 alkyl)aminocarbonyl" should be interpreted similarly.

[0041] As used herein, the term "C1-C6 alkylsulfanyl" refers to a group of the formula -SR a wherein R is generally a C1-C6 alkyl group as defined above. The terms "C1-C4 alkylsulfanyl" and "C1-C3 alkylsulfanyl" should be interpreted similarly. Examples of C1-C6 alkylsulfanyl include, but are not limited to, methylsulfanyl. a

[0042] As used herein, the term "C1-C6 alkylsulfinyl" refers to a group of the formula -S(O)R a wherein R is generally a C1-C6 alkyl group as defined above. The terms "C1-C4 alkylsulfinyl" and "C1-C3 alkylsulfinyl" should be interpreted similarly. Examples of C1-C6 alkylsulfinyl include, but are not limited to, methylsulfinyl. a

[0043] As used herein, the term "C1-C6 alkylsulfonyl" refers to a group of the formula -S(O)2R a wherein R is generally a C1-C6 alkyl group as defined above. The terms "C1-C4 alkylsulfonyl" and "C1-C3 alkylsulfonyl" should be interpreted similarly. Examples of C1-C6 alkylsulfonyl include, but are not limited to, methylsulfonyl. a

[0044] As used herein, the term "C1-C6 alkylsulfonamide" refers to the formula -NHS(O)2Ra refers to the group, and R a is generally a C1-C6 alkyl group as defined above.

[0045] The presence of one or more possible stereogenic elements in a compound of formula (I) means that the compound can exist in optically isomeric forms, i.e., enantiomeric or diastereomeric forms. Also, atropisomers can arise due to restricted rotation about a single bond. Formula (I) is intended to include all these possible isomeric forms and mixtures thereof. The present invention includes all these possible isomeric forms and mixtures thereof of the compounds of formula (I). Similarly, formula (I) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms of the compounds of formula (I).

[0046] In each case, the compounds of formula (I) according to the present invention are in free form, oxidized form as N-oxides, or salt form, for example, an agriculturally usable salt form. Compounds of formula (I) preferably form salts with amines including primary, secondary and tertiary amines (such as ammonia, dimethylamine and triethylamine), alkali metal and alkaline earth metal bases, transition metals or quaternary ammonium bases.

[0047] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing aromatic heterocyclic compounds. These are described, for example, in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton (1991).

[0048] The following list refers to the substituents R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , R 10Provide definitions (including preferred definitions) related thereto. For any one of these substituents, any of the definitions described below may be combined with any of the definitions of any other substituent described elsewhere in this written document or below.

[0049] R 1 is C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C1-C6 alkyl, or C3-C6 cycloalkyl. Preferably, R 1 is C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy C1-C4 alkyl, or C3-C6 cycloalkyl. More preferably, R 1 is C1-C3 alkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy C1-C3 alkyl, or C3-C4 cycloalkyl. Even more preferably, R 1 is methyl, ethyl, n-propyl, methoxy, 2-methoxyethyl, allyl, and prop-2-ynyl. Even more preferably, R 1 is methyl or ethyl. In a series of embodiments, R 1 is ethyl.

[0050] R 2 is phenyl or heteroaryl, and the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S, and each phenyl and heteroaryl moiety is optionally substituted with 1, 2, 3, or 4 groups which may be the same or different represented by R 7

[0051] Preferably, R 2 is phenyl or heteroaryl (wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), and each phenyl and heteroaryl moiety is 7It may be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by

[0052] More preferably, R 2 is phenyl or heteroaryl (wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1 or 2 heteroatoms each independently selected from N and O), and each phenyl and heteroaryl moiety may be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 7 It may be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by

[0053] Even more preferably, R 2 is phenyl or heteroaryl (wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1 or 2 heteroatoms each independently selected from N and O), and each phenyl and heteroaryl moiety may be optionally substituted with 1 or 2 groups which may be the same or different and are represented by R 7 It may be optionally substituted with 1 or 2 groups which may be the same or different and are represented by

[0054] Even more preferably, R 2 is phenyl which may be optionally substituted with 1 or 2 groups which may be the same or different and are represented by R 7 In one set of embodiments, R 2 is 3,4-dichlorophenyl or 3,4-difluorophenyl, preferably 3,4-dichlorophenyl.

[0055] R 4 is heteroaryl, the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1, 2 or 3 nitrogen atoms, and the heteroaryl moiety is bonded to the remainder of the molecule through a nitrogen atom in the heteroaryl ring, and each heteroaryl moiety may be optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are represented by R 9 It may be optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are represented by

[0056] Preferably, R 4is heteroaryl, the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1, 2 or 3 nitrogen atoms, and the heteroaryl moiety is bonded to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and each heteroaryl moiety is optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 9 and may be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R

[0057] More preferably, R 4 is heteroaryl, the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 2 or 3 nitrogen atoms, and the heteroaryl moiety is bonded to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and each heteroaryl moiety is optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 9 and may be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R

[0058] Even more preferably, R 4 is pyrazolyl, imidazolyl, triazolyl, wherein any of the pyrazolyl, imidazolyl and triazolyl moieties may each be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 9 and may be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R

[0059] In one set of embodiments, R 4 is heteroaryl, the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 2 nitrogen atoms, the heteroaryl moiety is bonded to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and the heteroaryl ring may be optionally substituted with 3 groups represented by R 9 and one R 9The group is selected from formyl, cyano, nitro, hydroxy, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C2-C6 alkenyloxy, cyano C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy, C1-C6 alkoxycarbonyl C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 alkylcarbonylamino, C1-C6 alkylamino, C1-C6 alkoxy C1-C6 alkylaminocarbonyl, C1-C6 alkoxy C1-C6 alkylcarbonylamino, C2-C6 alkenylcarbonylamino, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)amino, N,N-di(C1-C4 alkyl)aminocarbonyl, or benzyloxy, and any two adjacent Rs 9 groups may together with the carbon atom to which they are attached form a phenyl ring, and the resulting phenyl moiety is optionally substituted with only one R 10 group.

[0060] In another set of embodiments, R 4 is pyrazolyl, triazolyl, or indazolyl, and each moiety is optionally substituted with one or two substituents selected from cyano, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C2 alkoxy C1-C2 alkyl, C1-C2 alkylcarbonyl, and C3-C4 cycloalkyl. Preferably, R 4is pyrazolyl optionally substituted by one or two substituents selected from cyano, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C2 alkoxyC1-C2 alkyl, C1-C2 alkylcarbonyl, and C3-C4 cycloalkyl. More preferably, R 4 is pyrazolyl optionally substituted by only one substituent selected from halogen and C1-C3 haloalkyl, preferably chloro and trifluoromethyl.

[0061] In a particularly preferred set of embodiments, R 4 is 3-(trifluoromethyl)pyrazol-1-yl, 3-chloropyrazol-1-yl, 4-chloropyrazol-1-yl, 3-methylpyrazol-1-yl, 3-methoxypyrazol-1-yl, 3-isopropoxypyrazol-1-yl, 3-cyclopropylpyrazol-1-yl, 3-fluoropyrazol-1-yl, 3-(methoxymethyl)pyrazol-1-yl, 3-acetylpyrazol-1-yl, 3-ethoxypyrazol-1-yl, 3-(trifluoromethyl)pyrazol-1-yl, 3-isopropylpyrazol-1-yl, 6-fluoro-3-methyl-indazol-1-yl, 4-methoxyindazol-1-yl, 5-fluoroindazol-1-yl, 2,2-difluoroethoxy)pyrazol-1-yl, 3-cyanopyrazol-1-yl, 6-methoxyindazol-1-yl, 7-fluoroindazol-2-yl, or 3-chloro-1,2,4-triazol-1-yl. A particularly preferred set of embodiments is where R 4 is 3-(trifluoromethyl)pyrazol-1-yl, 3-chloropyrazol-1-yl, or 4-chloropyrazol-1-yl.

[0062] R 5 is hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl. Preferably, R 5is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, or C3-C6 cycloalkyl. More preferably, R 5 is hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, or C3-C5 cycloalkyl. Even more preferably, R 5 is hydrogen, halogen, C1-C3 alkyl, or C3-C4 cycloalkyl. Even more preferably still, R 5 is hydrogen or C1-C3 alkyl. Even more preferably still, R 5 is C1-C3 alkyl, preferably methyl.

[0063] R 7 is cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl or N,N-di(C1-C4 alkyl)aminocarbonyl.

[0064] Preferably, R 7 is cyano, nitro, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxyC1-C3 alkyl, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonamide, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl or N,N-di(C1-C3 alkyl)aminocarbonyl.

[0065] More preferably, R 7is cyano, nitro, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylsulfonamide, C1-C3 alkylcarbonyl, C1-C3 alkoxycarbonyl, C1-C3 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl or N,N-di(C1-C3 alkyl)aminocarbonyl.

[0066] More preferably, further, R 7 is cyano, nitro, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylcarbonyl, or C3-C6 cycloalkyl. Even more preferably, R 7 is cyano, nitro, chloro, fluoro, methyl, isopropyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy, methoxymethyl, acetyl, or cyclopropyl.

[0067] In a set of embodiments, R 7 is cyano, nitro, or halogen, preferably halogen, more preferably chloro or fluoro.

[0068] R 9is formyl, cyano, nitro, hydroxy, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C2-C6 alkenyloxy, cyano C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy, C1-C6 alkoxycarbonyl C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 alkylcarbonylamino, C1-C6 alkylamino, C1-C6 alkoxy C1-C6 alkylaminocarbonyl, C1-C6 alkoxy C1-C6 alkylcarbonylamino, C2-C6 alkenylcarbonylamino, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)amino, N,N-di(C1-C4 alkyl)aminocarbonyl, or benzyloxy; or any two adjacent R 9 groups, together with the carbon atom to which they are attached, may form a C3-C6 cycloalkyl ring or a phenyl ring, and the C3-C6 cycloalkyl and phenyl moieties are optionally substituted with 1, 2, 3, or 4 groups, which may be the same or different, represented by R 10 ; or any two adjacent R 9 groups, together with the carbon atom to which they are attached, may form a 5- or 6-membered heteroaryl ring, and the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S, and the heteroaryl moiety is optionally substituted with 1, 2, 3, or 4 groups, which may be the same or different, represented by R 10 ; or any two adjacent R 9The radical, together with the carbon atom to which it is attached, may form a 5- or 6-membered heterocyclyl ring, the heterocyclyl moiety being 5- or 6-membered and containing 1 or 2 heteroatoms selected from O and N, and the heteroaryl ring is optionally substituted with 1, 2, 3 or 4 radicals, which may be the same or different, represented by R 10 and optionally substituted with 1, 2, 3 or 4 radicals, which may be the same or different, represented by R

[0069] Preferably, R 9 is formyl, cyano, nitro, hydroxy, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C2-C6 alkenyloxy, cyano C1-C4 alkoxy, C1-C4 alkoxy C1-C4 alkyl, C1-C6 alkoxy C1-C6 alkoxy, C1-C4 alkoxycarbonyl C1-C4 alkoxy, C1-C6 alkoxycarbonyl, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 alkylcarbonylamino, C1-C6 alkylamino, C1-C6 alkoxy C1-C6 alkylaminocarbonyl, C1-C4 alkoxy C1-C4 alkylcarbonylamino, C2-C6 alkenylcarbonylamino, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)amino, N,N-di(C1-C3 alkyl)aminocarbonyl, or benzyloxy; or any two adjacent R 9 radicals, together with the carbon atom to which they are attached, may form a C3-C6 cycloalkyl ring or a phenyl ring, the C3-C6 cycloalkyl and phenyl moieties being optionally substituted with 1, 2 or 3 radicals, which may be the same or different, represented by R 10 ; or any two adjacent R 9The radical, together with the carbon atom to which it is attached, may form a 5- or 6-membered heteroaryl ring, the heteroaryl moiety being a 5- or 6-membered aromatic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S, the heteroaryl moiety being optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R 10 ; or optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R wherein any two adjacent R 9 radicals, together with the carbon atom to which they are attached, may form a 5- or 6-membered heterocyclyl ring, the heterocyclyl moiety being 5- or 6-membered and containing 1 or 2 heteroatoms selected from O and N, the heterocyclyl ring being optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R 10 .

[0070] More preferably, R 9 is acetyl, cyano, nitro, hydroxy, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C2-C4 alkenyloxy, cyano C1-C4 alkyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylsulfanyl, C1-C4 alkylsulfonyl, C1-C4 alkylcarbonyl, C1-C4 alkylcarbonylamino, C1-C4 alkoxyimino C1-C4 alkyl, C1-C4 alkoxy C1-C4 alkylcarbonylamino, C2-C4 alkenylcarbonylamino, C3-C4 cycloalkyl, phenyl or heteroaryl, the heteroaryl moiety being a 5- or 6-membered aromatic ring containing 1 or 2 heteroatoms individually selected from N, O, and S, and the phenyl and heteroaryl moieties being optionally substituted with 1 or 2 groups, which may be the same or different, represented by R 10 ; or wherein any two adjacent R radicals 9The radical, together with the carbon atom to which they are attached, may form a C5-C6 cycloalkyl ring or a phenyl ring, and the C5-C6 cycloalkyl and phenyl moieties may be optionally substituted with one or two identical or different groups represented by R 10 ; or any two adjacent R 9 groups, together with the carbon atom to which they are attached, may form a 5- or 6-membered heteroaryl ring, the heteroaryl moiety being a 5- or 6-membered aromatic ring containing one or two heteroatoms individually selected from N, O and S, and the heteroaryl moiety may be optionally substituted with one or two identical or different groups represented by R 10 ; or any two adjacent R 9 groups, together with the carbon atom to which they are attached, may form a 5- or 6-membered heterocyclyl ring, the heterocyclyl moiety being 5- or 6-membered and containing one or two heteroatoms selected from O and N, and the heterocyclyl ring may be optionally substituted with one or two identical or different groups represented by R 10 .

[0071] Even more preferably, R 9 is acetyl, cyano, nitro, hydroxy, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C2-C3 alkenyloxy, cyano C1-C2 alkyl, C1-C3 alkoxy C1-C3 alkyl, C1-C3 alkoxy C1-C3 alkoxy, C1-C2 alkoxycarbonyl, C1-C2 alkylsulfanyl, C1-C2 alkylsulfonyl, C1-C3 alkylcarbonyl, C1-C3 alkylcarbonylamino, C1-C2 alkoxyimino C1-C2 alkyl, C2-C3 alkenylcarbonylamino, cyclopropyl, phenyl or heteroaryl, the heteroaryl moiety being a 5- or 6-membered aromatic ring containing one or two heteroatoms individually selected from N, O and S, and the phenyl and heteroaryl moieties may be optionally substituted with a single R 10 group; or Any two adjacent Rs 9 groups, together with the carbon atom to which they are attached, may form a cyclohexyl or phenyl ring, and the phenyl moiety may be optionally substituted with one or two groups which may be the same or different as represented by R 10 ; or Any two adjacent Rs 9 groups, together with the carbon atom to which they are attached, may form a heteroaryl ring, the heteroaryl moiety being a 6-membered aromatic ring containing a single nitrogen atom, and the heteroaryl moiety may be optionally substituted with a single R 10 group; or Any two adjacent Rs 9 groups, together with the carbon atom to which they are attached, may form a 5- or 6-membered heterocyclyl ring, the heterocyclyl moiety being 5- or 6-membered and containing one or two heteroatoms selected from O and N, and the heterocyclyl ring may be optionally substituted with a single R 10 group.

[0072] In one set of embodiments, R 9 is cyano, halogen, C1-C4 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C2 haloalkoxy, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylcarbonyl, or C3-C4 cycloalkyl; or any two adjacent Rs 9 groups, together with the carbon atom to which they are attached, may form a phenyl ring which may be optionally substituted with only one R 10 group. Preferably, R 9 is cyano, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 alkoxyC1-C2 alkyl, C1-C2 alkylcarbonyl, or C3-C4 cycloalkyl; or any two adjacent Rs 9 groups, together with the carbon atom to which they are attached, may form a phenyl ring which may be optionally substituted with only one R 10 group.

[0073] R 10 is halogen, C1-C3 alkyl, or C1-C3 alkoxy. Preferably, R 10 is halogen or C1-C3 alkoxy. More preferably, R 10 is halogen or methoxy. Even more preferably, R 10 is fluoro or methoxy.

[0074] In the compound of formula (I) according to the present invention, preferably: R 1 is ethyl; R 2 is 3,4-dichlorophenyl or 3,4-difluorophenyl; R 4 is heteroaryl, the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 2 or 3 nitrogen atoms, the heteroaryl moiety is bonded to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and the heteroaryl moieties are each optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R 9 ; R 5 is methyl; R 9is formyl, cyano, nitro, hydroxy, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C2-C6 alkenyloxy, cyano C1-C4 alkoxy, C1-C4 alkoxy C1-C4 alkyl, C1-C6 alkoxy C1-C6 alkoxy, C1-C4 alkoxycarbonyl C1-C4 alkoxy, C1-C6 alkoxycarbonyl, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl, C1-C6 alkylcarbonylamino, C1-C6 alkylamino, C1-C6 alkoxy C1-C6 alkylaminocarbonyl, C1-C4 alkoxy C1-C4 alkylcarbonylamino, C2-C6 alkenylcarbonylamino, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)amino, N,N-di(C1-C3 alkyl)aminocarbonyl, or benzyloxy; or any two adjacent R 9 groups, together with the carbon atom to which they are attached, may form a C3-C6 cycloalkyl ring or a phenyl ring, and the C3-C6 cycloalkyl and phenyl moieties are optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R 10 ; or any two adjacent R 9 groups, together with the carbon atom to which they are attached, may form a 5- or 6-membered heteroaryl ring, and the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S, and the heteroaryl moiety is optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R 10 ; or any two adjacent R 9The base, together with the carbon atom to which they are attached, may form a 5- or 6-membered heterocyclyl ring, the heterocyclyl moiety being 5- or 6-membered and containing 1 or 2 heteroatoms selected from O and N, and the heterocyclyl ring is optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R 10 ; and is optionally substituted with 1, 2, or 3 groups, which may be the same or different, represented by R R 10 is halogen or C1-C3 alkoxy.

[0075] In another set of embodiments, R 1 is ethyl; R 2 is 3,4-dichlorophenyl; R 4 is 3-(trifluoromethyl)pyrazol-1-yl, 3-chloropyrazol-1-yl, or 4-chloropyrazol-1-yl; R 5 is methyl.

[0076] The compounds of the present invention can be formed as shown in the following scheme, where, unless otherwise specified, the definition of each variable element is as defined above for the compounds of formula (I). A general method for generating the compounds of formula (I) is described below. Unless otherwise specified in the text, R 1 R 2 R 4 and R 5 are as already defined herein. The starting materials used in the preparation of the compounds of the present invention can be purchased from normal commercial suppliers or prepared by known methods. The starting materials as well as the intermediates may be purified by state-of-the-art techniques such as chromatography, crystallization, distillation, and filtration before being used in the next step.

[0077] The compounds of formula (I) according to the present invention can be prepared from the compounds of formula (A) as shown below in Scheme 1.

[0078] Scheme 1:

Chem.

[0079] Scheme 2:

Chem.

[0080] Scheme 3:

Chem.

[0081] Scheme 4:

Chem.

[0082] Scheme 5:

Chemical formula

[0083] Scheme 6:

Chemical formula

[0084] The compounds of formula (i) and formula (J) are commercially available or can be prepared by methods known to those skilled in the art. This is shown in Scheme 6 above.

[0085] The present invention further provides a method for controlling weeds in a habitat, said method comprising applying to the habitat a composition comprising a compound of formula (I) in an amount effective for weed control. Moreover, the present invention may further provide a method for selectively controlling weeds in a habitat containing useful (crop) plants and weeds, wherein the method comprises applying to the habitat a composition according to the present invention in an amount effective for weed control. "Control" means extermination, reduction or inhibition of growth, or prevention or reduction of germination. It is noted that the compounds of the present invention exhibit considerably improved selectivity as compared to known structurally similar compounds. Generally, the plants to be controlled are unwanted plants (weeds). "Habitat" means an area where plants are growing or will grow. Application can be carried out on the habitat before and / or after germination of the crop plants. Some crop plants may be inherently resistant to the herbicidal effect of the compounds of formula (I).

[0086] The application rate of the compound of formula (I) can vary within wide limits and depends on the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application to furrows; without tillage application, etc.), the crop plant, the weeds to be controlled, prevailing weather conditions, and other factors depending on the method of application, the time of application and the target crop. The compounds of formula I according to the present invention are generally applied in amounts of from 10 to 2500 g / ha, in particular from 25 to 1000 g / ha, in particular from 25 to 250 g / ha.

[0087] Application is generally carried out by spraying the composition, typically with a large-area sprayer mounted on a tractor, but other methods such as dusting (in the case of powders), dripping or irrigation can also be used.

[0088] The term "useful plant" should also be understood to include useful plants that have been rendered resistant to herbicides such as bromoxynil, or to certain classes of herbicides such as, for example, 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, 5-enol-pyruvyl-shikimate-3-phosphate synthase (EPSPS) inhibitors, glutamine synthetase (GS) inhibitors or protoporphyrinogen-oxidase (PPO) inhibitors, by conventional breeding or genetic engineering methods. An example of a crop that has been rendered resistant to imidazolinones such as imazamox by conventional breeding methods (mutation induction) is Clearfield® summer rape (canola). Examples of crops that have been rendered resistant to herbicides or certain classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties marketed under the trade names RoundupReady®, Herculex I® and LibertyLink®.

[0089] The term "useful plant" should also be understood to include useful plants that have been transformed using recombinant DNA technology so as to be capable of synthesizing one or more selectively acting toxins, known, for example, from toxin-producing bacteria, in particular those of the genus Bacillus.

[0090] Examples of such plants are YieldGard® (maize varieties expressing the CryIA(b) toxin); YieldGard Rootworm® (maize varieties expressing the CryIIIB(b1) toxin); YieldGard Plus® (maize varieties expressing the CryIA(b) and CryIIIB(b1) toxins); Starlink® (maize varieties expressing the Cry9(c) toxin); Herculex I® (maize varieties expressing the CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton varieties expressing the CryIA(c) toxin); Bollgard I® (cotton varieties expressing the CryIA(c) toxin); Bollgard II® (cotton varieties expressing the CryIA(c) and CryIIA(b) toxins); VIPCOT® (cotton varieties expressing the VIP toxin); NewLeaf® (potato varieties expressing the CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta®.

[0091] Both the plant crop and its seed material can be tolerant to herbicides and, at the same time, tolerant to insect feeding (“stacked” transgenic events). For example, the seed can have the ability to express an insecticidal Cry3 protein while being tolerant to glyphosate at the same time.

[0092] Crop plants can also be obtained by conventional methods involving crossing or genetic manipulation and should be understood to include those containing so-called output traits (e.g., improved storage stability, higher nutritional value, and improved flavor).

[0093] The compound of formula (I) (or a composition containing the same) can be used for controlling unwanted plants (collectively referred to as "weeds"). The weeds to be controlled can be, for example, monocotyledonous species such as Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum, and, for example, dicotyledonous species such as Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium.

[0094] The compound of formula (I) can be used in its unmodified form or, preferably, in combination with adjuvants conventionally employed in the art of formulation to provide a herbicidal composition, using formulation adjuvants such as carriers, solvents and surface active agents (SAA). The present invention thus further provides a herbicidal composition comprising at least one compound of formula (I), an agriculturally acceptable carrier, and optionally an adjuvant. An agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art.

[0095] The herbicidal composition generally comprises from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of a compound of formula I and from 1 to 99.9% by weight of a formulation adjuvant, preferably from 0 to 25% by weight of a surfactant.

[0096] The composition can be selected from a number of formulation types. These include emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), oil-in-water emulsions (EO), water-in-oil emulsions (EW), micro-emulsions (ME), oil dispersions (OD), miscible flowables (OF), miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical concentrates (TK), dispersible concentrates (DC), soluble powders (SP), wettable powders (WP) and soluble granules (SG). The formulation type selected in any given case will depend on the particular intended purpose and on the physical, chemical and biological properties of the compound of formula (I).

[0097] Soluble powders (SP) can be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) or one or more water-soluble organic solids (such as polysaccharides), and optionally one or more wetting agents, one or more dispersing agents, or a mixture of said agents, to improve the dispersibility / solubility in water. The mixture is then ground to a fine powder. It is also possible to granulate a similar composition to form water-soluble granules (SG).

[0098] Wettable powders (WP) can be prepared by mixing a compound of formula (I) with one or more solid diluents or carriers, one or more wetting agents, and preferably one or more dispersing agents, and optionally one or more suspending agents, to promote dispersibility in liquids. The mixture is then ground to a fine powder. It is also possible for a similar composition to be granulated to form water-dispersible granules (WG).

[0099] The granules (GR) can be formed by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or by absorbing a compound of formula (I) (or a solution thereof in a suitable pharmaceutical) into a porous granular material (such as pumice, attapulgite clay, fuller's earth, kieselguhr, diatomaceous earth or ground corn cob), or by absorbing a compound of formula (I) (or a solution thereof in a suitable pharmaceutical) into a hard core material (such as sand, silicic acid, carbonate minerals, sulfates or phosphates), and optionally drying to form from pre-formed compressed powder granules. Agents commonly used to assist absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones, and esters) and fixing agents (such as polyvinyl acetate, polyvinyl alcohol, dextrin, carbohydrates and vegetable oils). One or more other additives may also be included in the granules (such as emulsifiers, wetting agents or dispersants).

[0100] The dispersible concentrate (DC) can be prepared by dissolving a compound of formula (I) in water or an organic solvent such as a ketone, alcohol or glycol ether. These solutions may contain a surfactant (such as to improve dilution with water or to prevent crystallization in the spray tank).

[0101] The emulsifiable concentrate (EC) or oil-in-water emulsion (EW) can be prepared by dissolving a compound of formula (I) in an organic solvent (optionally having one or more wetting agents, one or more emulsifiers or a mixture of said agents). Organic solvents suitably used in EC include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200 (SOLVESSO is a registered trademark)), ketones (such as cyclohexanone or methylcyclohexanone), and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethylamides of fatty acids (C8-C 10Examples include fatty acid dimethylamides, and chlorinated hydrocarbons. When added to water, the EC product can spontaneously emulsify to yield an emulsion with sufficient stability to enable spraying applications with suitable equipment.

[0102] In the preparation of EW, the compound of formula (I) is obtained as a liquid (which may be melted at a suitable temperature, typically below 70 °C if not liquid at room temperature) or in solution (by dissolving in a suitable solvent), and then the resulting liquid or solution is emulsified under high shear into water containing one or more SAAs to yield an emulsion. Suitable solvents for use in EW include vegetable oils, chlorinated hydrocarbons (such as chlorobenzene), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes), and other suitable organic solvents with low solubility in water.

[0103] Microemulsions (ME) can be prepared by mixing a blend of one or more solvents and one or more SAAs with water to spontaneously yield a thermodynamically stable isotropic liquid formulation. The compound of formula (I) is initially present either in water or in the solvent / SAA blend. Suitable solvents for use in ME include those described above for use in EC or EW. ME can be either oil-in-water or water-in-oil type systems (which can be determined by measuring the conductivity), and are suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. ME can remain as a microemulsion or form a conventional oil-in-water emulsion and be suitably diluted in water.

[0104] The suspension concentrate (SC) may contain an aqueous or non-aqueous suspension of fine insoluble solid particles of the compound of formula (I). The SC can be prepared by subjecting the solid compound of formula (I) in a suitable medium, optionally together with one or more dispersants, to a ball mill or bead mill to give a fine particle suspension of the compound. One or more wetting agents may be included in the composition, and a suspending agent may be included to reduce the sedimentation rate of the particles. Alternatively, the compound of formula (I) may be subjected to a dry mill and added to water containing the agents described above in the specification to give the desired final product.

[0105] The aerosol formulation contains the compound of formula (I) and a suitable propellant (e.g., n-butane). The compound of formula (I) may also be dissolved or dispersed in a suitable medium (e.g., water, or a hydratable liquid such as n-propanol) to give a composition for use in a non-pressurized manual spray pump.

[0106] The capsule suspension (CS) can be prepared in the same manner as the preparation of the EW formulation, but each of the oil droplets is encapsulated in a polymeric shell, and there is an additional polymerization stage such that an aqueous dispersion of oil droplets containing the compound of formula (I) and optionally a carrier or diluent therefor is obtained. The polymeric shell can be produced by either an interfacial polycondensation reaction or a coacervation technique. The composition can provide a sustained release of the compound of formula (I) and can be used for seed treatment. The compound of formula (I) may also be incorporated in a biodegradable polymer matrix such that the compound has a slow sustained release.

[0107] The composition may contain one or more additives in order to improve the biological performance of the composition, for example, by improving the wettability, retention or surface distribution of the compound of formula (I); the resistance to rain on the surface to be treated; or the uptake or mobility. Such additives include surfactants (SAA), oil-based spray additives such as certain mineral oils or natural vegetable oils (such as soybean oil and rapeseed oil), modified vegetable oils such as methylated rapeseed oil (MRSO), and blends thereof with other bio-enhancing adjuvants (formulation components that can assist or modify the action of the compound of formula (I)).

[0108] Wetting agents, dispersants and emulsifiers can be cationic, anionic, amphoteric or nonionic SAA.

[0109] Suitable cationic SAA include quaternary ammonium compounds (such as cetyltrimethylammonium bromide), imidazolines and amine salts.

[0110] Suitable anionic SAA include alkali metal salts of fatty acids, sulfates of aliphatic monoesters (such as sodium lauryl sulfate), salts of sulfonated aromatic compounds (such as sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalenesulfonate, and mixtures of sodium di-isopropyl-naphthalenesulfonate and sodium tri-isopropyl-naphthalenesulfonate), ether sulfates, alcohol ether sulfates (such as sodium laureth-3 sulfate), ether carboxylates (such as sodium laureth-3 carboxylate), phosphate esters (such as products from the reaction of one or more aliphatic alcohols with phosphoric acid (mainly monoesters) or phosphorus pentoxide (mainly di-esters), such as the reaction of lauryl alcohol with tetraphosphoric acid; also, these products may be ethoxylated), sulfosuccinamates, paraffin or olefin sulfonates, taurates, lignosulfonates, and phosphates / sulfates of tristyrylphenol.

[0111] Suitable amphoteric SAAs include betaines, propionates, and glycineates. Suitable nonionic SAAs include condensates of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or alkylphenols (such as octylphenol, nonylphenol, or octylcresol); partial esters derived from long-chain fatty acids or hexitol anhydrides; condensates of the partial esters with ethylene oxide; block polymers (including ethylene oxide and propylene oxide); alkanolamides; simple esters (such as fatty acid polyethylene glycol esters); amine oxides (such as lauryldimethylamine oxide); lecithin and its sorbitan and esters, alkyl polyglycosides, and tristyrylphenol. Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone, or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

[0112] The compounds of the present invention can also be used in mixtures with one or more additional herbicides and / or plant growth regulators. Examples of such additional herbicides or plant growth regulators include acetochlor, acifluorfen (including acifluorfen-sodium), acronifen, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, bentriazone, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, bilanafos, bipyrazone, bispyribac-sodium, bispyrazoxon, bromoxynil, butachlor, butaphenacil, carfentrazone (including carfentrazone-ethyl), chloransulam (including chloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotoluron, chlorsulfuron, cinmethylin, chlorthiophos, clethodim, clodinafop (including clodinafop-propargyl), chromazone, clopyralid, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cyhalofop (including cyhalofop-butyl), 2,4-D (including its choline salt and 2-ethylhexyl ester), 2,4-DB, desmedipham, dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), diclosulam, diflufenican, diflufenzoppil, dimethachlor, dimethenamid-P, dioxopyrimidon, diquat dibromide, diuron, epirifenacil, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxysulfuron, fenpyrazone, fenquinotrione, fentrazamide, flazasulfuron, florasulam, flupyradifurone (including flupyradifurone-benzyl), fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), flucraminopyril (including flucraminotefuryl), flufenacet, flufenoxymasyl, flumetsulam, flumioxazin, fluometuron,Fomesafen, flupyrasulfuron (including flupyrasulfuron-methyl-sodium), fluroxypyr (including fluroxypyr-meptyl), fluthiacet-methyl, fomesafen, foramsulfuron, glufosinate (including L-glufosinate and both ammonium salts), glyphosate (including its diammonium, isopropylammonium and potassium salts), halauxifen (including halauxifen-methyl), haloxyfop (including haloxyfop-methyl), hexazinone, hydantocidin, isoxaflutole, imazamox (including R-imazamox), imazapic, imazapyr, imazethapyr, indaziflam, indaziflam, indaziflam, iodosulfuron (including iodosulfuron-methyl-sodium), iodosulfuron (including iodosulfuron-methyl-sodium), iodosulfuron (including iodosulfuron-methyl-sodium), ioxynil, iptacoprid, isoproturon, isoxaflutole, rankotriione, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron-methyl), mesotrione, metamitron, metazachlor, methiozolin, metolachlor, metosulam, metribuzin, metsulfuron, napropamide,nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, fenmedifam, picloram, pinoxaden, pretilachlor, primisulfuron-methyl, prometryn, propanil, propaquizafop, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen-ethyl), pyraquinate, pyrazosulfuron-ethyl, pyridate, pyriftalid, pyrifluquinazon, pyrimisulfan, pyroxasulfone, pyroxasulfone, quinclorac, quinmerac, quizalofop (including quizalofop-P-ethyl and quizalofop-P-tefuryl), rimsulfuron, rimsulfuron, rimsulfuron, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn,Tetflupyrolimet, tien-carbazon, thifensulfuron, thiafenacyl, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, thifensulfuron-methyl, tribenuron (including tribenuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), triflumizole, trifluralin, triflusulfuron, tripyrasulfone, ethyl 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one, (4R)-1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one, (1RS,5SR)-3-[2-methoxy-4-(prop-1-yn-1-yl)phenyl]-4-oxobicyclo[3.2.1]oct-2-en-2-yl methyl carbonate, ethyl 2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy]acetate, methyl 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]-2-methoxy-acetate, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one,(2-Fluorophenyl)methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid, and methyl 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-3a,4,5,6-tetrahydro-6-methyl-6aH-cyclopenta[d]isoxazole-6a-carboxylate are mentioned.

[0113] The mixing partner of the compound of formula (I) may also be in the form of an ester or a salt, for example, as described in The Pesticide Manual, Nineteenth Edition, British Crop Protection Council, 2021.

[0114] The mixture can be advantageously used in the above formulations (in this case, the "active ingredient" relates to each mixture of the compound of formula (I) and the mixing partner).

[0115] The compounds or mixtures of the present invention can also be used in combination with one or more herbicide safeners. Examples of such safeners include benoxacor, cloquintocet (including cloquintocet mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenclorim, flurioxyphen, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifene, and oxabetrinil. Mixtures of the compound of formula I with cyprosulfamide, isoxadifen-ethyl, cloquintocet mexyl, and / or metcamifene are particularly preferred.

[0116] The safeners of the compound of formula (I) may also be, for example, as described in The Pesticide Manual, 19 thAs described in Edition (BCPC), 2021, it can be in the form of an ester or a salt. The reference to cloxintselt mexyl also applies to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as disclosed in International Publication No. 02 / 34048.

[0117] Preferably, the mixing ratio of the compound of formula (I) to the toxicity alleviant is from 100:1 to 1:10, especially from 20:1 to 1:1.

[0118] The compound of formula (I) is usually used in the form of an agrochemical composition and can be applied to the crop area or plant to be treated simultaneously or sequentially with further compounds. These further compounds can be, for example, fertilizers or trace element donors, or other preparations that affect plant growth. They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these preparations, and can optionally be accompanied by further carriers, surfactants or application-promoting adjuvants customarily used in the art of the formulation.

[0119] As used herein, the term "habitat" means a field in which a plant is growing, or a field in which seeds of a cultivated plant are sown, or a field in which seeds are to be sown in the soil. This includes the soil, seeds and seedlings as well as established vegetation.

[0120] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, petioles, foliage and fruits.

[0121] The term "plant propagation material" is understood to represent the reproductive parts of plants such as seeds that can be used for their propagation and vegetative parts such as cuttings or tubers such as potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants can be mentioned. Also mentioned are germinated plants and sprouts that are to be transplanted after germination or after emerging from the soil. These sprouts can be protected by complete or partial treatment by immersion before transplantation. Preferably, "plant propagation material" is understood to represent seeds.

[0122] The pesticides mentioned in this specification using common names are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.

[0123] The compounds of formula (I) can be used in the unmodified form or, preferably, together with adjuvants conventionally employed in the art of formulations. For this purpose, they can be conveniently formulated in known manner as emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusts, granules and capsules in, for example, polymeric substances. As well as the type of composition, the method of application such as spraying, atomizing, dusting, scattering, coating or pouring is selected according to the intended purpose and the circumstances at that time. The composition can also contain further adjuvants such as stabilizers, defoamers, viscosity regulators, binders or adhesives and fertilizers, sources of trace elements or other formulations for obtaining special effects.

[0124] Suitable carriers and adjuvants for use in agriculture can be solid or liquid and are substances useful in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0125] The compounds of formula (I) are usually used in the form of compositions and can be applied simultaneously or sequentially to the crop area or plants to be treated together with further compounds. These further compounds can be, for example, fertilizers or micronutrient donors or other preparations that affect plant growth. They can also be selective or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, and, if desired, are accompanied by further carriers, surfactants or application-promoting adjuvants customarily used in the art of formulations.

[0126] The compounds of formula (I) can be the sole active ingredient in the composition and can also be mixed, where appropriate, with one or more additional active ingredients such as pesticides, fungicides, synergists, herbicides or plant growth regulators. In some cases, the additional active ingredients can bring about unexpected synergistic activity.

[0127] Generally, the formulations contain 0.01 - 90% by weight of the active agent, 0 - 20% of an agriculturally acceptable surfactant and 10 - 99.99% of a solid or liquid inert formulation and adjuvant, and the active agent consists of at least the compound of formula (I) together with components (B) and (C) and optionally other active agents, in particular fungicides or preservatives, etc. The concentrated form of the composition generally contains about 2 - 80%, preferably about 5 - 70% by weight of the active agent. The application form of the formulation can contain, for example, 0.01 - 20% by weight, preferably 0.01 - 5% by weight of the active agent. Commercially available products will preferably be formulated as concentrates, but the end user will usually utilize the diluted formulation.

[0128] The following table shows formula (I) according to the invention:

Chemical formula

[0129]

Table 1

[0130] Table A-1 provides 26 compounds A-1.001 to A.1.026 of formula (I), where R 1 , R 2 , R 4 , and R 5 are as defined in Table 1.

[0131] Formulation Example

[0132] [Table 2]

[0133] A wettable powder can be obtained by sufficiently mixing the active ingredient with adjuvants, sufficiently grinding this mixture in a suitable mill, and diluting with water to obtain a suspension of a desired concentration.

[0134] [Table 3]

[0135] A powder that can be directly used for seed treatment can be obtained by sufficiently mixing the active ingredient with adjuvants and sufficiently grinding this mixture in a suitable mill.

[0136] Emulsifiable Concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether 3% (4 - 5 moles of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 moles of ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%

[0137] Any required dilution rate emulsion that can be used for plant protection can be obtained by diluting this concentrate with water.

[0138]

Table 4

[0139] The immediately available powder is obtained by mixing the active ingredient with a carrier and grinding this mixture in a suitable mill. Such a powder can also be used for the dry dressing of seeds.

[0140] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignosulfonate 2% Carboxymethyl cellulose 1% Kaolin 82%

[0141] Mix the active ingredient, grind it with adjuvants, and moisten this mixture with water. Extrude the mixture and then dry it in an air stream.

[0142] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (mol.wt.200) 3% Kaolin 89%

[0143] Apply the finely ground active ingredient uniformly in a mixer to kaolin moistened with polyethylene glycol. Coated granules that do not generate dust are obtained thereby.

[0144] Suspension concentrate Active ingredient [compound of formula (I)] 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6% Sodium lignosulfonate 10% Carboxymethyl cellulose 1% Silicone oil (in the form of a 75% aqueous emulsion) 1% Water 32%

[0145] The finely ground active ingredient is thoroughly mixed with adjuvants to obtain a suspension concentrate, from which suspensions with any desired dilution rate can be obtained by dilution with water. By such dilution, it is possible to treat living plants as well as plant propagation materials by spraying, pouring, or dipping, and protect them from ectoparasitism by microorganisms.

[0146] Flowable concentrate for seed treatment Active ingredient [compound of formula (I)] 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrylphenol + 10 - 20 moles of EO 2% 1,2 - Benzisothiazolin - 3 - one (in the form of a 20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% aqueous emulsion) 0.2% Water 45.3%

[0147] The finely ground active ingredient is thoroughly mixed with adjuvants to obtain a suspension concentrate, from which suspensions with any desired dilution rate can be obtained by dilution with water. By using such dilution, it is possible to treat living plants as well as plant propagation materials by spraying, pouring, or dipping, and protect them from ectoparasitism by microorganisms.

[0148] Sustained - release capsule suspension A combination of 28 parts of the compound of formula (I) is mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 part of a defoaming agent and 51.6 parts of water until the desired particle size is achieved. To this emulsion, a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 part of a thickening agent and 3 parts of a dispersing agent. This capsule suspension formulation contains 28% active ingredient. The medium capsule diameter is 8 - 15 microns. The resulting formulation is applied to the seeds as an aqueous suspension using an apparatus suitable for this purpose.

Example

[0149] The following non-limiting examples provide specific synthetic methods for representative compounds of the present invention as referred to in Table 2 below.

[0150] List of Abbreviations Å = angstrom, brs = broad singlet, °C = degree Celsius, d = doublet, dd = doublet of doublets, DMSO = dimethyl sulfoxide, HPLC = high performance liquid chromatography, M = molar amount, m = multiplet, MHz = megahertz, mL = milliliter, q = quartet, s = singlet, t = triplet, THF = tetrahydrofuran.

[0151] Example 1: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-[3-(trifluoromethyl)pyrazol-1-yl]pyridine-3-carboxylic acid (Compound 1) Step 1: Synthesis of methyl 3-(3,4-dichlorophenyl)-3-oxo-propanoate

Chemical formula

[0152] Step 2: Synthesis of methyl (Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoate

Chemical formula

[0153] Step 3: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylate

Chemical Structure

[0154] Step 4: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxo-pyridine-3-carboxylate

Chemical Structure

[0155] Step 5: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxo-pyridine-3-carboxylic acid

Chemical Structure

[0156] Step 6: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-[3-(trifluoromethyl)pyrazol-1-yl]pyridine-3-carboxylic acid

Chemical formula

[0157] Example 2: Synthesis of 5-(3-chloropyrazol-1-yl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylic acid (Compound 2)

Chemical formula

[0158] Example 3: Synthesis of 5-(3-chloropyrazol-1-yl)-2-(3,4-difluorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylic acid (Compound 4)

Chemical Structure

[0159] Throughout this description, temperature is indicated in degrees Celsius (°C) and "m.p." means melting point.

[0160]

Table 5

[0161] Biological Examples Seeds of various test species are sown in standard soil in pots (Ipomoea hederacea (IPOHE), Setaria faberi (SETFA), Zea mays (ZEAMX), Echinochloa crus-galli (ECHCG), Amaranthus palmeri (AMAPA), Amaranthus retoflexus (AMARE)). After cultivation in a greenhouse (24°C / 16°C, day / night; 14 hours of light; 65% humidity) for 8 days under controlled conditions, an aqueous spray solution derived from a formulation of industrial active ingredients in an acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5) is sprayed onto the plants. Unless otherwise specified, the compounds are applied at 1000 g / ha. The test plants are then grown in a greenhouse (24°C / 16°C, day / night; 14 hours of light; 65% humidity) under controlled conditions and watered twice daily. After 13 days, the test is evaluated for the percentage of damage to the plants. The biological activity is shown in the following table on a five-point scale (5 = 81 - 100%; 4 = 61 - 80%; 3 = 41 - 60%; 2 = 21 - 40%; 1 = 0 - 20%, -= not tested).

[0162]

Table 6

[0163]

Table 7

Claims

1. Equation (I): 【Chemistry 1】 (In the formula, R 1 is C 1 to C 6 alkyl, C 1 to C 6 alkoxy, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, or C 3 to C 6 cycloalkyl; R 2 is phenyl or heteroaryl, the heteroaryl portion is a five-membered or six-membered aromatic ring containing one, two, three or four heteroatoms individually selected from N, O and S, and each phenyl and heteroaryl portion is R 7 Represented by, which may be identical or different, and may be arbitrarily substituted with one, two, three, or four bases; R 4 R is a heteroaryl compound, the heteroaryl portion is a five-membered aromatic monocyclic ring containing one, two, or three nitrogen atoms, the heteroaryl portion is bonded to the remainder of the molecule via the nitrogen atoms in the heteroaryl ring, and each of the heteroaryl portions is R 9 Represented by, which may be identical or different, and may be arbitrarily substituted with one, two, three, or four bases; R 5 is hydrogen, halogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, or C 3 ~C 6 It is a cycloalkyl; R 7 These are cyano, nitro, halogen, and C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Haloalkoxy, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 6 Alkyl sulfanyl, C 1 ~C 6 Alkyl sulfinyl, C 1 ~C 6 Alkyl sulfonyl, C 1 ~C 6 Alkyl sulfonamide, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkylaminocarbonyl, or N,N-di(C 1 ~C 4 It is an alkyl)aminocarbonyl; R 9 is formyl, cyano, nitro, hydroxy, halogen, C 1 to C 6 alkyl, C 1 to C 6 alkoxy, C 1 to C 6 haloalkyl, C 1 to C 6 haloalkoxy, C 2 to C 6 alkenyloxy, cyano C 1 to C 6 alkoxy, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 1 to C 6 alkoxy C 1 to C 6 alkoxy, C 1 to C 6 alkoxycarbonyl C 1 to C 6 alkoxy, C 1 to C 6 alkoxycarbonyl, C 1 to C 6 alkylsulfanyl, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, C 1 to C 6 alkylsulfonamide, C 1 to C 6 alkylcarbonyl, C 1 to C 6 alkylaminocarbonyl, C 1 to C 6 alkylcarbonylamino, C 1 to C 6 alkylamino, C 1 to C 6 alkoxy C 1 to C 6 alkylaminocarbonyl, C 1 to C 6 alkoxy C 1 to C 6 alkylcarbonylamino, C 2 to C 6 Alkenylcarbonylamino, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkylaminocarbonyl, N,N-di(C 1 ~C 4 Alkyl)amino, N,N-di(C 1 ~C 4 Alkyl)aminocarbonyl, or benzyloxy; Any two adjacent R 9 The group, together with the carbon atom to which it is bonded, is C 3 ~C 6 A cycloalkyl ring or a phenyl ring may be formed, and the C 3 ~C 6 The cycloalkyl and phenyl portions are R 10 Represented by, which may be identical or different, and may be arbitrarily substituted with one, two, three or four bases; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heteroaryl ring, the heteroaryl portion being a five-membered or six-membered aromatic ring containing one, two, three, or four heteroatoms individually selected from N, O, and S, and the heteroaryl portion being R 10 Represented by, which may be identical or different, and may be arbitrarily substituted with one, two, three, or four bases; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring, the heterocyclyl portion being five-membered or six-membered and containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 10 Represented by, which may be identical or different, and may be arbitrarily substituted with one, two, three, or four bases; R 10 is halogen, C 1 ~C 3 Alkyl, or C 1 ~C 3 (It is an alkoxy) Compounds thereof; or their salts or N-oxides.

2. R 2 is phenyl or heteroaryl, the heteroaryl portion is a 5 or 6-membered aromatic ring containing one or two heteroatoms individually selected from N and O, and each phenyl and heteroaryl portion is R 7 The compound according to claim 1, which may be optionally substituted with one, two, or three groups that are identical or different, represented by .

3. R 2 R 7 The compound according to claim 1, which is a phenyl that may be optionally substituted with one or two groups that are identical or different, represented by .

4. R 5 is hydrogen or C 1 ~C 3 The compound according to claim 1, wherein it is alkyl.

5. R 7 These are cyano, nitro, halogen, and C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy, C 1 ~C 3 Haloalkyl, C 1 ~C 3 Haloalkoxy, C 1 ~C 3 Alkoxy C 1 ~C 3 Alkyl, C 1 ~C 3 Alkylcarbonyl, or C 3 ~C 6 The compound according to claim 1, wherein it is a cycloalkyl compound.

6. R 4 is a heteroaryl compound, the heteroaryl portion is a five-membered aromatic monocyclic ring containing one, two, or three nitrogen atoms, and the heteroaryl portion is bonded to the remainder of the molecule via the nitrogen atoms in the heteroaryl ring, and each of the heteroaryl portions is R 9 The compound according to claim 1, which may be optionally substituted with one, two, or three groups that are identical or different, represented by .

7. R 4 is a heteroaryl, the heteroaryl portion is a five-membered aromatic monocyclic ring containing two or three nitrogen atoms, the heteroaryl portion is bonded to the remainder of the molecule via the nitrogen atoms in the heteroaryl ring, and each of the heteroaryl portions is R 9 The compound according to claim 1, which may be optionally substituted with one, two, or three groups that are identical or different, represented by .

8. R 9 These are formyl, cyano, nitro, hydroxy, halogen, and C. 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Haloalkoxy, C 2 ~C 6 Alkenyloxy, Cyano C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkyl, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkoxy, C 1 ~C 4 Alkoxycarbonyl C 1 ~C 4 Alkoxy, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 4 Alkyl sulfanyl, C 1 ~C 4 Alkyl sulfinyl, C 1 ~C 4 Alkyl sulfonyl, C 1 ~C 4 Alkyl sulfonamide, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkylaminocarbonyl, C 1 ~C 6 Alkylcarbonylamino, C 1 ~C 6 Alkylamino, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkylaminocarbonyl, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkylcarbonylamino, C 2 ~C 6 Alkenylcarbonylamino, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkylaminocarbonyl, N,N-di(C 1 ~C 3 Alkyl)amino, N,N-di(C 1 ~C 3 Alkyl)aminocarbonyl, or benzyloxy; or Any two adjacent R 9 The group, together with the carbon atom to which it is bonded, is C 3 ~C 6 A cycloalkyl ring or a phenyl ring may be formed, and the C 3 ~C 6 The cycloalkyl and phenyl portions are R 10 Represented by, which may be identical or different, and may be arbitrarily substituted with one, two, or three bases; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heteroaryl ring, the heteroaryl portion being a five-membered or six-membered aromatic ring containing one, two, or three heteroatoms individually selected from N, O, and S, and the heteroaryl portion being R 10 Represented by, which may be identical or different, and may be arbitrarily substituted with one, two, or three bases; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring, the heterocyclyl portion being five-membered or six-membered and containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 10 Represented by, which may be the same or different, and may be arbitrarily substituted with one, two, or three bases, The compound according to claim 1.

9. R 9 These are formyl, cyano, nitro, halogen, and C 1 ~C 4 Alkyl, C 1 ~C 3 Alkoxy, C 1 ~C 3 Haloalkyl, C 1 ~C 2 Haloalkoxy, C 2 ~C 3 Alkenyloxy, Cyano C 1 ~C 2 Alkoxy, C 1 ~C 3 Alkoxy C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy C 1 ~C 3 Alkoxy, C 1 ~C 3 Alkoxycarbonyl C 1 ~C 3 Alkoxy, C 1 ~C 3 Alkoxycarbonyl, C 1 ~C 3 Alkyl sulfanyl, C 1 ~C 3 Alkyl sulfonyl, C 1 ~C 3 Alkylcarbonyl, C 1 ~C 3 Alkylaminocarbonyl, C 1 ~C 3 Alkylcarbonylamino, C 1 ~C 3 Alkylamino, C 1 ~C 3 Alkoxy C 1 ~C 3 Alkylaminocarbonyl, C 1 ~C 2 Alkoxy C 1 ~C 2 Alkylcarbonylamino, C 3 ~C 4 Alkenylcarbonylamino, C 3 ~C 4 Cycloalkyl, or N,N-di(C) 1 ~C 3 Alkyl)amino; or Any two adjacent R 9 The group, together with the carbon atom to which it is bonded, is C 5 ~C 6 A cycloalkyl ring or a phenyl ring may be formed, and the C 5 ~C 6 The cycloalkyl and phenyl portions have only one R 10 It may be arbitrarily replaced with; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a six-membered heteroaryl ring, the heteroaryl portion being a six-membered aromatic ring containing only one nitrogen atom, and the heteroaryl portion being a six-membered aromatic ring containing only one R 10 It may be arbitrarily substituted in the base; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring, the heterocyclyl portion being five-membered or six-membered and containing one or two heteroatoms selected from O and N, and the heterocyclyl ring having only one R 10 It may be arbitrarily substituted in the base, The compound according to claim 1.

10. R 10 is halogen or C 1 ~C 3 The compound according to claim 1, wherein it is an alkoxy.

11. A herbicide composition comprising the compound according to any one of claims 1 to 10 and an agriculturally acceptable compounding agent.

12. The herbicide composition according to claim 11, further comprising at least one additional pesticide.

13. The herbicide composition according to claim 12, wherein the additional pesticide is a herbicide or a herbicide toxicity mitigator.

14. A method for controlling the growth of unwanted plants, comprising the step of applying a compound of formula (I) according to any one of claims 1 to 10 to the unwanted plants or their habitat.

15. A method for preventing the growth of unwanted plants, comprising the step of applying the herbicide composition described in Claim 11 to the unwanted plants or their habitat.

16. Use of a compound of formula (I) according to any one of claims 1 to 10 as a herbicide.

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