Herbicidal derivatives

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】 TIFF2025520130000098.tif41160

Description

Technical Field

[0001] The present invention relates to a herbicidal pyridone derivative as an active ingredient having, for example, herbicidal activity. The present invention also relates to a pesticidal composition containing at least one pyridone derivative, a process for preparing these compounds, and the use of the pyridone derivative or composition in the control of weeds in agricultural or horticultural crops of particularly useful plants.

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 (I):

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 invention, there is provided a pesticidal composition comprising a herbicidally effective amount of a compound of formula (I) according to the invention. Such agricultural compositions 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 for controlling weeds in a habitat, the method comprising the step of applying to the habitat a composition comprising a compound of formula (I) in an amount effective for weed control.

[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 that it may or may not have one or more equivalent or different substituents, for example, one, two or three Rs 7 and may or may not have substituents. For example, C1-C6 alkyl substituted by one, two or three halogens is not particularly limited, and examples thereof include -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, C1-C6 alkoxy substituted by one, two or three halogens is not particularly limited thereto, and examples thereof 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 "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo).

[0011] As used herein, the term "hydroxy" or "hydroxyl" means a -OH group.

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

[0013] As used herein, the term "acetyl" means a -C(O)CH3 group.

[0014] As used herein, =O means an oxo group found, for example, in a carbonyl (-C(=O)-) group.

[0015] As used herein, the term "C1-C6 alkyl" refers to a straight-chain or branched-chain hydrocarbon chain group consisting only of carbon and hydrogen atoms, containing no unsaturation, having 1 to 6 carbon atoms, and being bonded to the remainder of the molecule by a single bond. The terms "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. The term "C1-C6 alkylene" refers to the corresponding definition of C1-C6 alkyl, except that such a group is bonded 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 defined above that is substituted by one or more identical 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" is of the formula -OR where R a is a C1-C6 alkyl group generally defined above. arefers to a group. The terms "C1-C4 alkoxy" and "C1-C3 alkoxy" should be interpreted in the same way. 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 by one or more identical or different halogen atoms. The terms "C1-C4 haloalkoxy" and "C1-C3 haloalkoxy" should be interpreted in the same way. Examples of C1-C6 haloalkoxy include, but are not limited to, trifluoromethoxy.

[0019] 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 having 2 to 6 carbon atoms bonded to the rest of the molecule by a single bond. The term "C2-C3 alkenyl" should be interpreted in the same way. Examples of C2-C6 alkenyl include, but are not limited to, ethenyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), and but-1-enyl.

[0020] 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 bonded to the rest of the molecule by a single bond. The term "C2-C3 alkynyl" should be interpreted in the same way. Examples of C2-C6 alkynyl include, but are not limited to, ethynyl, prop-1-ynyl, and but-1-ynyl.

[0021] As used herein, the term "C1-C6 alkoxy C1-C6 alkyl" refers to the formula R bOR a - group (wherein 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). The terms "C1 - C4 alkoxy C1 - C4 alkyl" and "C1 - C3 alkoxy C1 - C3 alkyl" should be interpreted similarly.

[0022] As used herein, the term "C3 - C6 cycloalkyl" refers to a monocyclic saturated ring system and a group containing 3 - 6 carbon atoms. The terms "C3 - C5 cycloalkyl" and "C3 - C4 cycloalkyl" should be interpreted similarly. Examples of C3 - C6 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0023] 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. Examples of C3 - C6 cycloalkylaminocarbonyl include, but are not limited to, cyclopropylcarbamoyl (i.e., cyclopropylaminocarbonyl).

[0024] As used herein, the term "phenyl C1 - C2 alkyl" refers to a phenyl ring attached to the remainder of the molecule via a C1 - C2 alkylene linker as defined above. Examples of phenyl C1 - C2 alkyl include, but are not limited to, benzyl and phenylethyl.

[0025] As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring group containing 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen, and sulfur. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl.

[0026] As used herein, the term "heteroaryl C1-C2 alkyl" refers to a heteroaryl ring generally as defined above, attached to the remainder of the molecule via a C1-C2 alkylene linker as defined above.

[0027] As used herein, the term "C1-C6 alkylcarbonyl" refers to a group of the formula -C(O)R a wherein R a is generally a C1-C6 alkyl group as defined above. Examples of C1-C6 alkylcarbonyl include, but are not limited to, acetyl.

[0028] As used herein, the term "C1-C6 alkoxycarbonyl" refers to a group of the formula -C(O)OR a wherein R a is generally a C1-C6 alkyl group as defined above.

[0029] As used herein, the term "C1-C6 alkylaminocarbonyl" refers to a group of the formula -C(O)NHR a wherein R a is generally a C1-C6 alkyl group as defined above. Examples of C1-C6 alkylaminocarbonyl include, but are not limited to, ethylcarbamoyl (i.e., ethylaminocarbonyl).

[0030] As used herein, the term "N,N-di(C1-C4 alkyl)amino" refers to a group of the formula -N(R a )(R b ), wherein each R a and R b is, independently, generally a C1-C4 alkyl group as defined above. The term "N,N-di(C1-C3 alkyl)amino" should be interpreted similarly.

[0031] As used herein, the term "N,N-di(C1-C4 alkyl)aminocarbonyl" refers to a group of the formula -C(O)N(R a )(R b ), wherein each R a and R b is, independently, generally a C1-C4 alkyl group as defined above. The term "N,N-di(C1-C3 alkyl)aminocarbonyl" should be interpreted similarly. Examples of N,N-di(C1-C4 alkyl)aminocarbonyl include, but are not limited to, dimethylcarbamoyl (i.e., N,N-di(methyl)aminocarbonyl).

[0032] As used herein, the term "C1-C6 alkylsulfanyl" refers to a group of the formula -SR a wherein R a 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.

[0033] As used herein, the term "C1-C6 alkylsulfinyl" refers to a group of the formula -S(O)R a wherein R arefers to a group. The terms "C1-C4 alkylsulfinyl" and "C1-C3 alkylsulfinyl" should be interpreted in the same way. Examples of C1-C6 alkylsulfinyl include, but are not limited to, methylsulfinyl.

[0034] As used herein, the term "C1-C6 alkylsulfonyl" refers to a group of the formula -S(O)2R a wherein R is a C1-C6 alkyl group as generally defined above. a The terms "C1-C4 alkylsulfonyl" and "C1-C3 alkylsulfonyl" should be interpreted in the same way. Examples of C1-C6 alkylsulfanyl include, but are not limited to, methylsulfonyl.

[0035] As used herein, the term "C1-C6 alkylsulfonamide" refers to a group of the formula -NHS(O)2R a wherein R a is generally a C1-C6 alkyl group as defined above.

[0036] The presence of one or more possible stereodiene elements in the compound of formula (I) means that the compound can exist in optical isomeric forms, i.e., enantiomeric or diastereomeric forms. Also, atropisomers can arise due to the restriction of 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 compound of formula (I). Similarly, formula (I) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms of the compound of formula (I).

[0037] In each case, the compound of formula (I) according to the invention is in free form or in salt form, for example in an agriculturally usable salt form. Compounds of formula (I) preferably form salts with amines containing primary, secondary and tertiary amines (such as ammonia, dimethylamine and triethylamine), alkali metal and alkaline earth metal bases, transition metals or quaternary ammonium bases. In a particularly preferred set of embodiments, the compound of formula (I) can form a chloride salt or a 2,2,2-trifluoroacetate salt. In an even more preferred set of embodiments, the compound of formula (I) can form a 2,2,2-trifluoroacetate salt.

[0038] The following list provides definitions (including preferred definitions) for substituents R 1 、R 2 、R 3 、R 4 、R 5 、and R 6 with reference to the compound of formula (I). For any one of these substituents, any of the definitions described below may be combined with any of the definitions of any of the other substituents described elsewhere in this document or below.

[0039] R 1 is C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxyC1-C6 alkyl or C3-C6 cycloalkyl. Preferably, R 1 is C1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxyC1-C4 alkyl or C3-C6 cycloalkyl. More preferably, R 1 is C1-C4 alkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxyC1-C3 alkyl or C3-C4 cycloalkyl.

[0040] In one set of embodiments, R 1is methyl, ethyl, n-propyl, allyl, prop-2-ynyl, methoxy, methoxyethyl or cyclopropyl. In other sets of embodiments, R 1 is C1-C4 alkyl, preferably C1-C3 alkyl, more preferably methyl or ethyl, and even more preferably ethyl.

[0041] 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 and are represented by R 7

[0042] 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 optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 7

[0043] 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 individually selected from N and O), and each phenyl and heteroaryl moiety is optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 7

[0044] 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 individually selected from N and O, and wherein each phenyl and heteroaryl moiety is R 7Optionally substituted with one or two groups, which may be the same or different, represented by

[0045] More preferably, R 2 is phenyl optionally substituted with one or two groups, which may be the same or different, represented by R 7 In one set of embodiments, R 2 is 3-chloro-4-cyanophenyl, 3,4-dichlorophenyl, 3-chloro-4-isopropoxyphenyl or 3,4-difluorophenyl. Preferably, R 2 is 3-chloro-4-cyanophenyl, 3,4-dichlorophenyl or 3,4-difluorophenyl, more preferably 3,4-dichlorophenyl.

[0046] R 3 is hydrogen or C1-C6 alkyl. Preferably, R 3 is hydrogen.

[0047] R 4 is hydrogen, halogen, C1-C6 alkyl or C1-C6 haloalkyl. Preferably, R 4 is hydrogen, halogen, C1-C3 alkyl, or C1-C3 haloalkyl. More preferably, R 4 is hydrogen or C1-C3 alkyl. In one set of embodiments, R 4 is hydrogen or methyl. In other sets of embodiments, R 4 is hydrogen.

[0048] R 5 is phenyl or heteroaryl, where 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 where 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 9 and where R 5When it is a 5-membered heteroaryl, the heteroaryl moiety is attached to the remainder of the molecule via a carbon atom.

[0049] Preferably, R 5 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 wherein each phenyl and heteroaryl moiety may be optionally substituted with 1, 2 or 3 groups, which may be the same or different, represented by R 9 , and when R 5 is a 5-membered heteroaryl, the heteroaryl moiety is attached to the remainder of the molecule via a carbon atom.

[0050] More preferably, R 5 is phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1 or 2 heteroatoms individually selected from N, O and S, and wherein each phenyl and heteroaryl moiety may be optionally substituted with 1 or 2 groups, which may be the same or different, represented by R 9 , and when R 5 is a 5-membered heteroaryl, the heteroaryl moiety is attached to the remainder of the molecule via a carbon atom.

[0051] Even more preferably, R 5 is phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thienyl, thiazolyl, isothiazolyl, oxazolyl or isoxazolyl, wherein each of the aforementioned R 5 groups may be optionally substituted with 1 or 2 groups, which may be the same or different, represented by R 9 .

[0052] Even more preferably, R 5 is phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or thiazolyl, wherein each of the aforementioned R 5 groups may be optionally substituted with 1 or 2 groups, which may be the same or different, represented by R9 Optionally substituted with one or two groups, which may be the same or different, represented by

[0053] In one set of embodiments, R 5 is phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thienyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl or quinoxalinyl, where each of the aforementioned R 5 groups may be optionally substituted with one or two groups, which may be the same or different, represented by R 9 Optionally substituted with one or two groups, which may be the same or different, represented by

[0054] In a further set of embodiments, R 5 is phenyl, pyridyl, pyrimidinyl or thiazolyl, where each of the aforementioned R 5 may be optionally substituted with one or two groups, which may be the same or different, represented by R 9 Optionally substituted with one or two groups, which may be the same or different, represented by

[0055] R 5 In certain embodiments where R is a 6-membered heteroaryl moiety substituted with a hydroxy group, this moiety may be in the keto (i.e., when the hydroxy group appears as an oxo group) or enol form. This example is when R 5 is 6-oxo-1H-pyrimidin-4-yl, 6-oxo-1H-pyridin-2-yl or 6-oxo-1H-pyridazin-5-yl, and when the pyrimidinyl, pyridinyl and pyridazinyl moieties may be substituted with a further group represented by R 9 Preferably, when R is a 6-membered heteroaryl moiety substituted with a hydroxy group, this moiety may be in the keto (i.e., when the hydroxy group appears as an oxo group) or enol form, and R 5 is 6-oxo-1H-pyrimidin-4-yl, 6-oxo-1H-pyridin-2-yl, 5-cyano-6-oxo-1H-pyridin-2-yl or 6-oxo-1H-pyridazin-5-yl. 5 is 6-oxo-1H-pyrimidin-4-yl, 6-oxo-1H-pyridin-2-yl, 5-cyano-6-oxo-1H-pyridin-2-yl or 6-oxo-1H-pyridazin-5-yl.

[0056] R 6 is hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy or C1-C6 alkoxy C1-C6 alkyl. Preferably, R 6 is hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy or C1-C4 alkoxy C1-C4 alkyl. More preferably, R 6 is hydrogen, C1-C3 alkyl, C1-C3 alkoxy or C1-C3 alkoxy C1-C3 alkyl. In one embodiment, R 6 is hydrogen or C1-C3 alkyl, preferably hydrogen or methyl, and more preferably, R 6 is hydrogen.

[0057] R 7 is cyano, nitro, amino, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxy C1-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.

[0058] Preferably, R 7 is cyano, nitro, amino, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy C1-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.

[0059] More preferably, R7 is cyano, nitro, amino, 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.

[0060] Even more preferably, 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.

[0061] In one set of embodiments, R 7 is cyano, halogen or C1-C3 alkoxy, preferably cyano, chloro, fluoro or isopropoxy.

[0062] In other sets of embodiments, R 7 is cyano, nitro or halogen, preferably R 7 is halogen, more preferably R 7 is chloro or fluoro. Even more preferably, R 7 is chloro.

[0063] R 9is cyano, nitro, hydroxy, 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, hydroxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, 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, wherein the C3-C6 cycloalkyl and phenyl moieties may be optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are 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, wherein 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 wherein the 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 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, wherein the heterocyclyl moiety is 5- or 6-membered and contains 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are represented by R 10 ; or

[0064] Preferably, R 9is cyano, nitro, hydroxy, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C4 alkoxyC1-C4 alkyl, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylsulfonamide, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, hydroxycarbonyl, C1-C4 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, 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, wherein the C3-C6 cycloalkyl and phenyl moieties are optionally substituted with 1, 2 or 3 groups which may be the same or different and are 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, 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 wherein the heteroaryl moiety is optionally substituted with 1, 2 or 3 groups which may be the same or different and are 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, wherein the heterocyclyl moiety is 5- or 6-membered and contains 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring is optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 10 ; or

[0065] More preferably, R 9is cyano, nitro, hydroxy, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C3 alkoxyC1-C3 alkyl, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylsulfonamide, C1-C3 alkylcarbonyl, C1-C3 alkoxycarbonyl, hydroxycarbonyl, C1-C3 alkylaminocarbonyl, C3-C4 cycloalkyl, C3-C4 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)aminocarbonyl or benzyloxy.

[0066] Even more preferably, R 9 is cyano, nitro, hydroxy, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C2 alkoxyC1-C2 alkyl, C1-C2 alkylsulfanyl, C1-C2 alkylsulfinyl, C1-C2 alkylsulfonyl, C1-C2 alkylsulfonamide, C1-C2 alkylcarbonyl, C1-C2 alkoxycarbonyl, hydroxycarbonyl, C1-C2 alkylaminocarbonyl, C3-C4 cycloalkyl, C3-C4 cycloalkylaminocarbonyl, N,N-di(C1-C2 alkyl)aminocarbonyl or benzyloxy.

[0067] In one set of embodiments, R 9 is cyano, hydroxy, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, hydroxycarbonyl or C3-C6 cycloalkyl. Preferably, R 9is cyano, hydroxy, halogen, C1-C4 alkyl, C1-C3 alkoxy, C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 alkoxyC1-C2 alkyl, C1-C2 alkylsulfanyl, C1-C2 alkylsulfonyl, C1-C2 alkylcarbonyl, C1-C2 alkoxycarbonyl, hydroxycarbonyl or C3-C4 cycloalkyl. More preferably, R 9 is cyano, hydroxy, chloro, fluoro, C1-C6 alkyl, C1-C3 alkoxy, C1-C2 haloalkyl, trifluoromethoxy, methoxymethyl, methylsulfanyl, methylsulfonyl, acetyl, methoxycarbonyl, hydroxycarbonyl or cyclopropyl. Even more preferably, R 9 is cyano, hydroxy, chloro, fluoro, methyl, ethyl, n-propyl, isopropyl, isobutyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, difluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, trifluoromethoxy, methoxymethyl, methylsulfonyl, acetyl, methoxycarbonyl, hydroxycarbonyl or cyclopropyl.

[0068] In another set of embodiments, R 9 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C2 alkylsulfanyl or C3-C4 cycloalkyl.

[0069] In a further set of embodiments, R 9 is halogen, C1-C3 alkyl, trifluoromethyl, methylsulfanyl or cyclopropyl.

[0070] 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.

[0071] In the compound of formula (I) according to the present invention, preferably: R 1 is C1-C3 alkyl; R 2 is phenyl optionally substituted with one or two groups, which may be the same or different, represented by R 7 ; R 3 is hydrogen; R 4 is hydrogen; R 5 is phenyl or heteroaryl, where the heteroaryl moiety is a 5- or 6-membered aromatic ring containing one or two heteroatoms individually selected from N and S, and where each phenyl and heteroaryl moiety is optionally substituted with one or two groups, which may be the same or different, represented by R 9 ; R 6 is hydrogen; R 7 is halogen; and R 9 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C2 alkylsulfanyl or C3-C4 cycloalkyl.

[0072] In other sets of embodiments, R 1 is ethyl; R 2 is 3,4-dichlorophenyl; R 3 is hydrogen; R 4 is hydrogen; R 5 is phenyl or heteroaryl, where the heteroaryl moiety is a 5- or 6-membered aromatic ring containing one or two heteroatoms individually selected from N and S, and where each phenyl and heteroaryl moiety is optionally substituted with one or two groups, which may be the same or different, represented by R 9Optionally substituted with one or two groups, which may be the same or different, represented by; R 6 is hydrogen; and R 9 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C2 alkylsulfanyl or C3-C4 cycloalkyl.

[0073] In a further set of embodiments, R 1 is ethyl; R 2 is 3-chloro-4-cyanophenyl, 3,4-dichlorophenyl, 3-chloro-4-isopropoxyphenyl or 3,4-difluorophenyl; R 3 is hydrogen; R 4 is hydrogen; R 5 is phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, thienyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl or quinoxalinyl, where each of the aforementioned R 5 groups may be optionally substituted with one or two groups, which may be the same or different, represented by R 9 ; R 9 is cyano, hydroxy, chloro, fluoro, methyl, ethyl, n-propyl, isopropyl, isobutyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, difluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, trifluoromethoxy, methoxymethyl, methylsulfonyl, acetyl, methoxycarbonyl, hydroxycarbonyl or cyclopropyl.

[0074] The compounds of the present invention can be formed as shown in the following scheme, where, unless otherwise specified, the definitions of each variable element are 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 3 、R 4 、R 5 and R 6 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 can be 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.

[0075] The compounds of formula (A) of the present invention can be prepared from the compounds of formula (A) as shown below in Scheme 1. Scheme 1:

Chemical formula

[0076] The compound of formula (A) (wherein R 3 is hydrogen and R 5 is aryl or heteroaryl) can be prepared by hydrolysis of the compound of formula (A) (wherein R 5 is aryl and R 3 is C1-C6 alkyl) with a suitable base (such as sodium hydroxide or lithium hydroxide) or a suitable acid (such as trifluoroacetic acid, hydrochloric acid, formic acid or sulfuric acid) in a suitable solvent (such as methanol, ethanol, dichloromethane, chloroform, ethyl acetate or tetrahydrofuran) with any co-solvent (such as water). When a base is used, the product is obtained after acidification with a suitable acid (such as hydrochloric acid).

[0077] In an alternative conversion, the compound of formula (A) (wherein R 3and R 6 are both hydrogen, and R 5 is aryl or heteroaryl), in a suitable solvent (such as methanol, ethanol, dichloromethane, chloroform, ethyl acetate or tetrahydrofuran, etc.) with an optional co-solvent (such as water), by a suitable base (such as sodium hydroxide or lithium hydroxide) or a suitable acid (such as trifluoroacetic acid, hydrochloric acid, formic acid or sulfuric acid, etc.), the compound of formula (A) (wherein R 5 is aryl or heteroaryl, R 3 is C1-C6 alkyl, and R 6 is an ester) can be prepared by a one-pot hydrolysis-decarboxylation reaction. When a base is used, the product is obtained after acidification with a suitable acid (such as hydrochloric acid).

[0078] The compound of formula (A) can also be prepared by the method described below. Scheme 2:

Chemical formula

[0079] The compound of formula (B) (wherein Y is Br (or I), R 3 is C1-C6 alkyl, and R 6 is hydrogen) is obtained by Suzuki-Miyaura cross-coupling with an arylboronic acid (such as (3-chlorophenyl)boronic acid) or het-arylboronic acid (such as (2-fluoro-4-pyridyl)boronic acid) similar to the conditions in the literature, to give the compound of formula (A) (wherein R 5can be converted to (wherein R is aryl or heteroaryl). Typically, this reaction is carried out in the presence of an optional ligand (such as (4-(N,N-dimethylamino)phenyl)di-tert-butylphosphine), a suitable catalyst (such as methanesulfonato(1,1-bis(di-t-butylphosphino)ferrocene)(2'-amino-1,1'-biphenyl-2-yl)palladium(II), 4-di-tert-butylphosphanyl-N,N-dimethylaniline; methanesulfonic acid; N-methyl-2-phenylaniline; palladium or chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II), etc.), or in the presence of palladium diacetate, in the presence of a base (such as tripotassium phosphate), in a suitable organic solvent (such as toluene, acetonitrile or cyclopentyl methyl ether, etc.), optionally in the presence of water, at a high temperature, with a compound of formula (B) and R 5 -boronic acid or boroxine. This is shown above in Scheme 2.

[0080] In an alternative conversion, a compound of formula (A) (wherein R 6 is an ester group (bonded by ester carbonyl), and R 5 is aryl or heteroaryl) is subjected to an α-arylation reaction with an aryl or heteroaryl R 5 -X (such as 1-bromo-2-chloro-benzene or 1-chloro-2-iodobenzene, etc.) in the presence of a suitable catalyst (such as chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II), etc.), optionally with a ligand (such as tri-tert-butylphosphane; tetrafluoroborate, etc.), in the presence of a base (such as tripotassium phosphate), in a suitable solvent (such as 1,4-dioxane or 2-methylbutan-2-ol, etc.), at a high temperature, to obtain a compound of formula (B) (wherein Y is hydrogen, and R 6 is an ester group (bonded by ester carbonyl)).

[0081] In another conversion, a compound of formula (A) (wherein R 6is an ester group (bonded by ester carbonyl), and R 5 is heteroaryl) is obtained by the reaction of a compound of formula (B) (wherein Y is hydrogen and R 5 -F (such as 5-chloro-2-fluoro-pyridine) or R 5 -Cl (such as 2,5-dichloropyrimidine) in the presence of a base (such as tripotassium phosphate) in a suitable solvent (such as methylsulfinylmethane) at a high temperature by a nucleophilic aromatic substitution reaction. 6 is an ester group (bonded by ester carbonyl)).

[0082] Scheme 3:

Chemical formula

[0083] In another transformation, the compound of formula (C) can be converted to a compound of formula (B) (wherein Y is a halogen (such as Br or I) and R 5 is hydrogen) by reaction with a halogenating agent (such as iodine) in the presence of a base (such as bis(2,2,6,6-tetramethyl-1-piperidyl)zinc, magnesium chloride or lithium chloride) in a suitable solvent (such as tetrahydrofuran) at a low temperature.

[0084] Scheme 4:

Chemical formula

[0085] Scheme 5:

Chemical formula

[0086] Scheme 6:

Chemical formula

[0087] Compounds of formula (H) and formula (i) are commercially available and can also be prepared by methods well known to those skilled in the art.

[0088] Scheme 7:

Chemical formula

[0089] The compounds of formula (J) and formula (K) are commercially available or can be prepared by methods well known to those skilled in the art.

[0090] The present invention further provides a method for controlling weeds in a habitat, said method comprising applying to the habitat a composition comprising an amount of a compound of formula (I) effective for weed control. Moreover, the present invention can further provide a method for selectively controlling weeds in a habitat containing useful (crop) plants and weeds, wherein this 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 should be noted that the compounds of the present invention exhibit considerably improved selectivity 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 compound of formula (I).

[0091] The application rate of the compound of formula (I) can vary within a wide range and depends on the nature of the soil, the method of application (pre-emergence or post-emergence; seed dressing; application to furrows; no 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 compound of formula I according to the present invention is generally applied in an amount of 10 - 2500 g / ha, especially 25 - 1000 g / ha, particularly 25 - 250 g / ha.

[0092] Application is generally effected 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 may also be used.

[0093] The term "useful plants" should also be understood to include useful plants which 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 which has been rendered resistant to imidazolinones such as imazamox by conventional breeding (mutation induction) is Clearfield® summer rape (canola). Examples of crops which have been rendered resistant to herbicides or certain classes of herbicides by genetic engineering methods are the glyphosate- and glufosinate-resistant maize varieties marketed under the trade names RoundupReady®, Herculex I® and LibertyLink®.

[0094] The term "useful plants" should also be understood to include useful plants which have been transformed using recombinant DNA techniques such that they are capable of synthesizing one or more selectively acting toxins, such as those known from toxin-producing bacteria, in particular those of the genus Bacillus.

[0095] 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®.

[0096] Plant crops or their seed materials can both be resistant to herbicides and, at the same time, resistant to insect feeding (a "stacked" transgenic event). For example, seeds can have the ability to express an insecticidal Cry3 protein while, at the same time, being resistant to glyphosate.

[0097] Crop plants can also be obtained by conventional methods involving mating or genetic manipulation and are understood to include those containing so-called output traits (such as improved storage stability, higher nutritional value, and improved flavor).

[0098] 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.

[0099] 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.

[0100] The herbicidal composition generally comprises 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compound of formula (I) and preferably 0 to 25% by weight of a surfactant, and 1 to 99.9% by weight of a formulation adjuvant.

[0101] The composition can be selected from a number of formulation types. These include emulsion concentrate (EC), suspension concentrate (SC), suspoemulsion (SE), capsule suspension (CS), water-dispersible granule (WG), emulsifiable granule (EG), oil-in-water emulsion (EO), water-in-oil emulsion (EW), micro-emulsion (ME), oil dispersion (OD), miscible flowable (OF), miscible liquid (OL), soluble concentrate (SL), ultra-low volume suspension (SU), ultra-low volume liquid (UL), technical concentrate (TK), dispersible concentrate (DC), soluble powder (SP), wettable powder (WP), and soluble granule (SG). The formulation type selected in any case will depend on the specific intended purpose and on the physical, chemical, and biological properties of the compound of formula (I).

[0102] The soluble powder (SP) can be prepared by mixing the compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate, or magnesium sulfate) 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 into a fine powder. A similar composition can also be granulated to form water-soluble granules (SG).

[0103] The wettable powder (WP) can be prepared by mixing the 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 a liquid. The mixture is then ground into a fine powder. A similar composition may be granulated to form water-dispersible granules (WG).

[0104] The granule (GR) can be formed by granulating a mixture of the compound of formula (I) and one or more powdered solid diluents or carriers, or by absorbing the 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 the compound of formula (I) (or a solution thereof in a suitable pharmaceutical) into a hard core material (such as sand, silicic acid, carbonate mineral, sulfate or phosphate), 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 granule (such as emulsifiers, wetting agents or dispersants).

[0105] The dispersible concentrate (DC) can be prepared by dissolving the 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).

[0106] The emulsifiable concentrate (EC) or oil-in-water emulsion (EW) can be prepared by dissolving the 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.

[0107] 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.

[0108] Microemulsion (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 previously described for use in EC or EW. ME can be either an oil-in-water or water-in-oil type system (which can be determined by measuring the conductivity), and is 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.

[0109] 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 provide 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 provide the desired final product.

[0110] 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 provide a composition for use in a non-pressurized manual spray pump.

[0111] 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.

[0112] 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 distribution on the surface 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 of these with other bio-enhancing adjuvants (formulation components that can assist or modify the action of the compound of formula (I)).

[0113] Wetting agents, dispersants and emulsifiers can be cationic, anionic, amphoteric or nonionic SAA.

[0114] Suitable cationic SAA include quaternary ammonium compounds (such as cetyltrimethylammonium bromide), imidazolines and amine salts.

[0115] 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.

[0116] Suitable amphoteric SAAs include betaines, propionates, and glycineates.

[0117] 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 said 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.

[0118] Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone, or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

[0119] 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, aminocarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, bentriazone, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, bilanafos, bipyrazone, bispyribac-sodium, bixlozone, bromoxynil, butachlor, butaphenacil, carfentrazone (including carfentrazone-ethyl), chloransulam (including chloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotoluron, chlorsulfuron, cinmethylin, clodinafop, 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, dioxopyrimetryn, diquat dibromide, diuron, epoxiconazole, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flazasulfuron, florasulam, flupyradifurone (including flupyradifurone-benzyl), fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), flucraminopyril (including flucraminopyril-tefuryl), flufenacet, flufenoxymethasulfuron, flumetsulam, flumioxazin, flumuron,Fomesafen, fluazifop (including fluazifop-methyl), fluthiamide, fomesafen, halosulfuron, 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, ioxynil, iproctazid, isoproturon, isoxaflutole, rankotriol, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron-methyl), mesotrione, metazachlor, methiozolin, metolachlor, metosulam, metribuzin, metsulfuron, napropamide, nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, phenmedipham, picloram, pinoxaden, pretilachlor, primisulfuron-methyl, prometryn, propanil, propaquizafop, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen-ethyl), pyraquinate, pyrazosulfotole, pyridate, pyriftalid, pyrifluobenzoxime, pyrimisulfan, pyroxasulfone, pyroxasulam, cinchonachlor, cinmethylin, quizalofop (including quizalofop-P-ethyl and quizalofop-P-tefuryl), 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), triflumizoxazin, 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-ylmethyl 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.

[0120] 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, Ninetheenth Edition, British Crop Protection Council, 2021.

[0121] The mixture can advantageously be used in the above-mentioned formulations (in this case, the "active ingredient" relates to each mixture of the compound of formula (I) and the mixing partner).

[0122] 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.

[0123] The safeners for the compound of formula (I) may also be, for example, as described in The Pesticide Manual, 19 hAs described in the Edition (BCPC), 2021, it can be in the form of an ester or a salt. The reference to cloxintocet 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.

[0124] 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.

[0125] 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, if desired, can be accompanied by further carriers, surfactants or application-promoting adjuvants conventionally used in the art of the formulation.

[0126] 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.

[0127] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, petioles, foliage and fruits.

[0128] 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. Examples can include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Also included 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 prior to transplantation. Preferably, "plant propagation material" is understood to represent seeds.

[0129] The pesticidal agents referred to in this specification using common names are known, for example, from "The Pesticide Manual", 19th Ed., British Crop Protection Council 2021.

[0130] 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.

[0131] 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.

[0132] The compounds of formula (I) are usually used in the form of compositions and can be applied to the crop area or plants to be treated either simultaneously or sequentially with further compounds. These further compounds can be, for example, fertilizers or trace element donors or other preparations which influence the growth of plants. 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 customary in the art of the formulation.

[0133] The compounds of formula (I) can be the sole active ingredient in the composition and can also, where appropriate, be mixed 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.

[0134] As a rule, the formulations comprise 0.01 to 90% by weight of active ingredient, 0 to 20% of agriculturally acceptable surfactants and 10 to 99.99% of solid or liquid inert formulation components and adjuvants, the active ingredient consisting at least of the compounds of formula (I) together with component (B) and (C) and optionally with further active ingredients, in particular fungicides or preservatives etc. The concentrated forms of the compositions generally contain about 2 to 80%, preferably about 5 to 70% by weight of active ingredient. The application forms of the formulations can contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight of active ingredient. Commercially available products will preferably be formulated as concentrates, but the end user will generally use the diluted formulations.

[0135] The following table illustrates examples of individual compounds of formula (I) according to the invention

Chemical formula

[0136]

Table 1-1

Table 1-2

Table 1-3

[0137] Table A-1 provides 65 compounds A-1.001 to A.1.065 of formula (I), where R 3 is hydrogen, and R 1 , R 2 , R 4 , R 5 and R 6 are as defined in Table 1.

[0138] Formulation Example

Table 2

[0139] The active ingredient is thoroughly mixed with adjuvants, and the mixture is thoroughly ground in a suitable mill and diluted with water to obtain a wettable powder that can be used to obtain a suspension of the desired concentration.

[0140]

Table 3

[0141] The active ingredient is thoroughly mixed with adjuvants, and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be directly used for seed treatment.

[0142] 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% 50% xylene mixture

[0143] Emulsions of any required dilution that can be used for plant protection are obtainable from this concentrate by dilution with water.

[0144]

Table 4

[0145] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding this mixture in a suitable mill. Such powders can also be used for the dry dressing of seeds.

[0146] Extruded granules 15% active ingredient [compound of formula (I)] 2% sodium lignosulfonate 1% carboxymethylcellulose 82% kaolin

[0147] The active ingredient is mixed and ground with adjuvants, and this mixture is moistened with water. The mixture is extruded and then dried in an air stream.

[0148] Coated granules 8% active ingredient [compound of formula (I)] 3% polyethylene glycol (mol.wt. 200) 89% kaolin

[0149] In a mixer, the finely ground active ingredient is uniformly applied to kaolin moistened with polyethylene glycol. Coated granules that do not generate dust are thereby obtained.

[0150] Suspension concentrate 40% active ingredient [compound of formula (I)] 10% propylene glycol 6% nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) Sodium lignosulfonate 10% Carboxymethyl cellulose 1% Silicone oil (in the form of a 75% aqueous emulsion) 1% Water 32%

[0151] 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.

[0152] Flowable concentrate for seed treatment Active ingredient [compound of formula (I)] 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrylphenol + 10 - 20 mol 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%

[0153] 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.

[0154] 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 as an aqueous suspension to the seeds with a suitable device for this purpose.

Example

[0155] The following non-limiting examples provide specific synthetic methods for representative compounds of the present invention as referred to in Table 2 below.

[0156] Throughout this specification, temperature is indicated in degrees Celsius (°C) and "m.p." means melting point.

[0157] List of Abbreviations Å = angstrom, brd = broad doublet, brs = broad singlet, °C = degrees Celsius, d = doublet, dd = doublet of doublets, DMSO = dimethyl sulfoxide, M = molar amount, m = multiplet, MHz = megahertz, nm = nanometer, q = quartet, s = singlet, t = triplet.

[0158] Example 1: Synthesis of 6-[(3-chlorophenyl)methyl]-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylic acid (Compound 1) Step 1: Synthesis of methyl 3-(3,4-dichlorophenyl)-3-oxo-propanoate

Chem.

[0159] Step 2: Synthesis of methyl (Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoate

Chemical Structure

[0160] Step 3: Synthesis of 6-(bromomethyl)-2,2-dimethyl-1,3-dioxin-4-one

Chemical Structure

[0161] Step 4: Synthesis of methyl 6-(bromomethyl)-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylate

Chem.

[0162] Step 5: Synthesis of methyl 6-[(3-chlorophenyl)methyl]-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylate

Chem.

[0163] Step 6: Synthesis of 6-[(3-chlorophenyl)methyl]-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylic acid

Chemical formula

[0164] Example 2: Synthesis of 2-(3,4-dichlorophenyl)-6-[(3,5-dimethoxyphenyl)methyl]-1-ethyl-4-oxo-pyridine-3-carboxylic acid (Compound 2) Step 1: Synthesis of ethyl 3-(3,4-dichlorophenyl)-3-oxo-propanoate

Chemical formula

[0165] Step 2: Synthesis of ethyl (Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoate

Chemical Structure

[0166] Step 3: Synthesis of ethyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylate

Chemical Structure

[0167] Step 4: Synthesis of ethyl 2-(3,4-dichlorophenyl)-6-(2-ethoxy-2-oxo-ethyl)-1-ethyl-4-oxo-pyridine-3-carboxylate

Chemical formula

[0168] Step 5: Synthesis of ethyl 2-(3,4-dichlorophenyl)-6-[1-(3,5-dimethoxyphenyl)-2-ethoxy-2-oxo-ethyl]-1-ethyl-4-oxo-pyridine-3-carboxylate

Chemical Structure

[0169] Step 6: Synthesis of 2-(3,4-dichlorophenyl)-6-[(3,5-dimethoxyphenyl)methyl]-1-ethyl-4-oxo-pyridine-3-carboxylic acid

Chemical Structure

[0170] Example 3: Synthesis of 6-benzyl-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylic acid (Compound 3) Step 1: Synthesis of 6-benzyl-2,2-dimethyl-1,3-dioxin-4-one

Chemical Structure

[0171] Step 2: Synthesis of methyl 6-benzyl-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylate

Chemical Structure

[0172] Step 3: Synthesis of 6-benzyl-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylic acid

Chemical formula

[0173] Example 4: Synthesis of 6 - [(5 - chloropyrimidin - 2 - yl)methyl] - 2 - (3,4 - dichlorophenyl) - 1 - ethyl - 4 - oxo - pyridine - 3 - carboxylic acid (Compound 4) Step 1: Synthesis of methyl 2 - (3,4 - dichlorophenyl) - 1 - ethyl - 6 - methyl - 4 - oxo - pyridine - 3 - carboxylate

Chemical formula

[0174] Step 2: Synthesis of methyl 2 - (3,4 - dichlorophenyl) - 6 - (2 - ethoxy - 2 - oxo - ethyl) - 1 - ethyl - 4 - oxo - pyridine - 3 - carboxylate

Chemical formula

[0175] Step 3: Synthesis of methyl 6-[1-(5-chloropyrimidin-2-yl)-2-ethoxy-2-oxo-ethyl]-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylate

Chemical Structure

[0176] Step 3: Synthesis of 6-[(5-chloropyrimidin-2-yl)methyl]-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylic acid

Chemical formula

[0177] Example 5: Synthesis of 6-[(5-chloro-2-pyridyl)methyl]-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylic acid (Compound 5) Step 1: Synthesis of methyl 6-[1-(5-chloro-2-pyridyl)-2-ethoxy-2-oxo-ethyl]-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylate

Chemical Structure

[0178] Step 2: Synthesis of 6-[(5-chloro-2-pyridyl)methyl]-2-(3,4-dichlorophenyl)-1-ethyl-4-oxo-pyridine-3-carboxylic acid

Chemical Structure

[0179]

Table 5-1

Table 5-2

Table 5-3

Table 5-4

Table 5-5

Table 5-6

Table 5-7

Table 5-8

Table 5-9

Table 5-10

Table 5-11

Table 5-12

Table 5-13

Table 5-14

Table 5-15

Table 5-16

Table 5-17

Table 5-18

Table 5-19

Table 5-20

Table 5-21

Table 5-22

Table 5-23

Table 5-24

Table 5-25

Table 5-26

Table 5-27

Table 5-28

Table 5-29

Table 5-30

Table 5-31

Table 5-32

Table 5-33

Table 5-34

Table 5-35

Table 5-36

Table 5-37

Table 5-38

Table 5-39

Table 5-40

Table 5-41

Table 5-42

Table 5-43

Table 5-44

Table 5-45

Table 5-46

Table 5-47

Table 5-48

Table 5-49

Table 5-50

Table 5-51

[0180] Biological Examples Seeds of various test species are sown in standard soil (Ipomoea hederacea (IPOHE), Zea mays (ZEAMX), Echinochloa crus-galli (ECHCG), Amaranthus palmeri (AMAPA), Amaranthus retoflexus (AMARE), and Setaria faberi (SETFA)). 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 obtained from a formulation of the technically active ingredient 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. The application rates are shown in g / ha in the following table. The test plants are then cultivated in a greenhouse (24°C / 16°C, day / night; 14 hours of light; 65% humidity) under controlled conditions and watered twice a day. After 13 days, the test is evaluated for the percentage of damage inflicted on the plants. The biological activity is shown in the following table on a 5-point scale (5 = 81 - 100%; 4 = 61 - 80%; 3 = 41 - 60%; 2 = 21 - 40%; 1 = 0 - 20%; -= not tested).

[0181]

Table 6-1

Table 6-2

Table 6-3

Table 6-4

[0182]

Table 7-1

Table 7-2

Table 7-3

Table 7-4

Claims

1. Formula (I): 【Chemical 1】 (wherein 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, wherein said 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 wherein each phenyl and heteroaryl moiety is optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are represented by R 7 ; and may be optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are represented by R R 3 is hydrogen or C 1 ~C 6 alkyl; R 4 is hydrogen, halogen, C 1 to C 6 alkyl or C 1 to C 6 haloalkyl; R 5 is phenyl or heteroaryl, wherein said 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 wherein each phenyl and heteroaryl moiety is optionally substituted with 1, 2, 3 or 4 groups which may be the same or different as represented by R 9 , and wherein, when R 5 is 5-membered heteroaryl, said heteroaryl moiety is attached to the remainder of the molecule via a carbon atom; R 6 is hydrogen, halogen, C 1 to C 6 alkyl, C 1 to C 6 alkoxy or C 1 to C 6 alkoxy C 1 to C 6 alkyl; R 7 is cyano, nitro, halogen, C 1 -C 6 -C alkyl, C 1 -C 6 -C alkoxy, C 1 -C 6 -C haloalkyl, C 1 -C 6 -C haloalkoxy, C 1 -C 6 -C alkoxyC 1 -C 6 -C alkyl, C 1 -C 6 -C alkylsulfanyl, C 1 -C 6 -C alkylsulfinyl, C 1 -C 6 -C alkylsulfonyl, C 1 -C 6 -C alkylsulfonamide, C 1 -C 6 -C alkylcarbonyl, C 1 -C 6 -C alkoxycarbonyl, C 1 -C 6 -C alkylaminocarbonyl, C 3 -C 6 -C cycloalkyl, C 3 -C 6 -C cycloalkylaminocarbonyl or N,N-di(C 1 -C 4 -C alkyl)aminocarbonyl; R 9 is 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 1 to C 6 alkoxyC 1 to C 6 alkyl, 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 alkoxycarbonyl, hydroxycarbonyl, C 1 to C 6 alkylaminocarbonyl, C 3 to C 6 cycloalkyl, C 3 to C 6 cycloalkylaminocarbonyl, N,N - di(C 1 to C 4 alkyl)aminocarbonyl or benzyloxy; or Any two adjacent R 9 groups, together with the carbon atom to which they are attached, may form a C 3 -C 6 -cycloalkyl ring or a phenyl ring, where the C 3 -C 6 -cycloalkyl and phenyl moieties may be optionally substituted with 1, 2, 3 or 4 groups which may be the same or different as represented by R 10 ; or Any two adjacent Rs 9 groups, together with the carbon atoms to which they are attached, may form a 5- or 6-membered heteroaryl ring, where 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 where the heteroaryl moiety is optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and which are represented by R 10 ; or optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and which are represented by R 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, wherein said heterocyclyl moiety is 5- or 6-membered and contains one or two heteroatoms selected from O and N, and wherein said heterocyclyl ring is optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are represented by R 10 ; and R 10 is halogen, C 1 ~C 3 alkyl or C 1 ~C 3 alkoxy). the compound, or a salt or N-oxide thereof.

2. R 1 is C 1 to C 4 alkyl, C 1 to C 3 alkoxy, C 2 to C 3 alkenyl, C 2 to C 3 alkynyl, C 1 to C 3 alkoxy C 1 to C 3 alkyl or C 3 to C 4 cycloalkyl, the compound according to claim 1.

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

4. R 4 The compound according to any one of claims 1 to 3, wherein R is hydrogen.

5. R 5 is phenyl or heteroaryl, where said heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2 or 3 heteroatoms individually selected from N, O and S, and where each phenyl and heteroaryl moiety is optionally substituted with 1, 2 or 3 groups, which may be the same or different, represented by R 9 and where, when R 5 is 5-membered heteroaryl, said heteroaryl moiety is attached to the remainder of the molecule via a carbon atom, a compound according to any one of claims 1 to 4.

6. R 5 is phenyl or heteroaryl, wherein said heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1 or 2 heteroatoms individually selected from N and S, and wherein each phenyl and heteroaryl moiety is optionally substituted with 1 or 2 groups, which may be the same or different, represented by R 9 and wherein, when R 5 is 5-membered heteroaryl, said heteroaryl moiety is attached to the remainder of the molecule via a carbon atom, A compound according to any one of claims 1 to 5.

7. R 6 The compound according to any one of claims 1 to 6, wherein R is hydrogen.

8. R 7 is cyano, halogen or C 1 to C 3 alkoxy, and the compound according to any one of claims 1 to 7.

9. R 9 is cyano, hydroxy, chloro, fluoro, C 1 -C 6 alkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkyl, trifluoromethoxy, methoxymethyl, methylsulfanyl, methylsulfonyl, acetyl, methoxycarbonyl, hydroxycarbonyl or cyclopropyl, a compound according to any one of claims 1 to 7.

10. R 2 is 3-chloro-4-cyanophenyl, 3,4-dichlorophenyl, 3-chloro-4-isopropoxyphenyl or 3,4-difluorophenyl, and is a compound according to any one of claims 1 to 9.

11. A herbicidal composition comprising the compound according to any one of Claims 1 to 10 and an agriculturally acceptable formulation adjuvant.

12. The herbicidal composition according to Claim 11, further comprising at least one additional pesticidal agent.

13. The herbicidal composition according to Claim 12, wherein the additional pesticidal agent is a herbicide or a herbicide toxicity alleviating agent.

14. A method for controlling weeds in a habitat, the method comprising the step of applying a controlling amount of the composition according to any one of Claims 11 to 13 to the habitat of the weeds.

15. Use of the compound of formula (I) according to any one of Claims 1 to 10 as a herbicide.

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