Herbicidal derivatives

Abstract

Compounds having the formula (I) wherein the substituents are as defined in claim 1 are disclosed. The invention further relates to herbicidal compositions comprising compounds of formula (I) and to the use of compounds of formula (I) for controlling weeds, in particular in crops of useful plants. # imgabs0 #

Description

[0001] The present invention relates to herbicidal pyridone derivatives (e.g. as active ingredients) which have herbicidal activity. The invention also relates to agrochemical compositions comprising at least one of these pyridone derivatives, processes for the preparation of these compounds, and the use of these pyridone derivatives or compositions in agriculture or horticulture for controlling weeds, in particular weeds in crops of useful plants.

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

[0003] According to the present invention, there is provided a compound having formula (I) or a salt or N-oxide thereof:

[0004]

[0005] in

[0006] R 1 is C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxyC1-C6 alkyl, or C3-C6 cycloalkyl;

[0007] R 2 is phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms independently selected from N, O and S, and wherein each phenyl and heteroaryl moiety may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 7 The group represented by is substituted;

[0008] R 4 is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1, 2 or 3 nitrogen atoms, and wherein the heteroaryl moiety is attached to the rest of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl moiety may each be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 9 The group represented by is substituted;

[0009] R 5 is hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl;

[0010] R 7is 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 alkylsulfonylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, or N,N-di(C1-C4 alkyl)aminocarbonyl;

[0011] R 9 is formyl, cyano, nitro, hydroxyl, 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 alkylsulfonylamino, 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;

[0012] Any two adjacent R 9 The groups together with the carbon atoms 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 replaced by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 10 or

[0013] Any two adjacent R 9 The groups together with the carbon atoms 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 independently selected from N, O and S, and wherein the heteroaryl moiety may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are composed of R 10 or

[0014] Any two adjacent R 9The 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 a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are composed of R 10 The group represented by is substituted;

[0015] R 10 It is halogen, C1-C3 alkyl, or C1-C3 alkoxy.

[0016] Surprisingly, it has been found that the novel compounds of formula (I) have a very advantageous level of herbicidal activity for practical purposes.

[0017] 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.

[0018] According to a third aspect of the present invention there is provided a method of controlling weeds at a locus, the method comprising applying to the locus a weed controlling amount of a composition comprising a compound of formula (I).

[0019] According to a fourth aspect of the present invention, there is provided use of a compound of formula (I) as a herbicide.

[0020] When substituents are indicated as being "optionally substituted", this means that they may or may not carry one or more identical or different substituents, for example one, two or three R 9 Substituents. For example, C1-C6 alkyl substituted with 1, 2 or 3 halogens may include, but are not limited to -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, C1-C6 alkoxy substituted with 1, 2 or 3 halogens may include, but are not limited to CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O- or CH3CF2O- groups.

[0021] As used herein, the term "cyano" refers to a -CN group.

[0022] As used herein, the term "hydroxy" or "hydroxyl" refers to an -OH group.

[0023] As used herein, the term "halogen" refers to fluorine (fluorine / fluoro), chlorine (chlorine / chloro), bromine (bromine / bromo), or iodine (iodine / iodo).

[0024] As used herein, the term "nitro" refers to a -NO2 group.

[0025] As used herein, the term "formyl" refers to a -C(O)H group.

[0026] As used herein, the term "acetyl" refers to a -C(O)CH3 group.

[0027] As used herein, the term "C1-C6 alkyl" refers to a straight or branched hydrocarbon chain group consisting only of carbon atoms and hydrogen atoms, which contains no unsaturation, has one to six carbon atoms, and is attached to the rest of the molecule by a single bond. "C1-C4 alkyl" and "C1-C3 alkyl" should be interpreted accordingly. Examples of C1-C6 alkyls include, but are not limited to, methyl, ethyl, n-propyl and isomers thereof, such as isopropyl. "C1-C6 alkylene" refers to the corresponding definition of C1-C6 alkyl, except that this group is attached to the rest of the molecule by two single bonds. The term "C1-C2 alkylene" should be interpreted accordingly. Examples of C1-C6 alkylenes include, but are not limited to -CH2-, -CH2CH2- and -(CH2)3-.

[0028] As used herein, the term "C1-C6 haloalkyl" refers to a C1-C6 alkyl group as generally defined above that is substituted with one or more halogen atoms that are the same or different. The terms "C1-C4 haloalkyl" and "C1-C3 haloalkyl" should be interpreted accordingly. Examples of C1-C6 haloalkyl groups include, but are not limited to, trifluoromethyl.

[0029] As used herein, the term "C1-C6 alkoxy" refers to a group having the formula -OR a A group in which R a is a C1-C6 alkyl group as generally defined above. The terms "C1-C4 alkoxy" and "C1-C3 alkoxy" should be interpreted accordingly. Examples of C1-C6 alkoxy groups include, but are not limited to, methoxy, ethoxy, 1-methylethoxy (isopropoxy), and propoxy.

[0030] As used herein, the term "C1-C6 haloalkoxy" refers to a C1-C6 alkoxy group as generally defined above that is substituted with one or more halogen atoms that are the same or different. The terms "C1-C4 haloalkoxy" and "C1-C3 haloalkoxy" should be interpreted accordingly. Examples of C1-C6 haloalkoxy include, but are not limited to, trifluoromethoxy.

[0031] As used herein, the term "cyano C1-C6 alkoxy" refers to a C1-C6 alkoxy group as generally defined above that is substituted with one or more cyano groups. The terms "cyano C1-C4 alkoxy" and "cyano C1-C3 alkoxy" should be interpreted accordingly. Examples of cyano C1-C6 alkoxy groups include, but are not limited to, cyanoethoxy.

[0032] As used herein, the term "C2-C6 alkenyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one double bond which may have an (E)- or (Z)-configuration, having two to six carbon atoms, attached to the remainder of the molecule by a single bond. The term "C2-C3 alkenyl" should be interpreted accordingly. Examples of C2-C6 alkenyl include, but are not limited to, ethenyl / vinyl, prop-1-enyl, prop-2-enyl (allyl), but-1-enyl.

[0033] As used herein, the term "C2-C6 alkynyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having two to six carbon atoms, and attached to the remainder of the molecule by a single bond. The term "C2-C3 alkynyl" should be interpreted accordingly. Examples of C2-C6 alkynyl include, but are not limited to, ethynyl, prop-1-ynyl, but-1-ynyl.

[0034] As used herein, the term "C2-C6 alkenyloxy" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one double bond which may have an (E)- or (Z)-configuration, having from two to six carbon atoms, attached to the remainder of the molecule via an oxygen linker.

[0035] As used herein, the term "C1-C6 alkoxy C1-C6 alkyl" refers to a b OR a - a group, wherein R b is a C1-C6 alkyl group as generally defined above, and R a is a C1-C6 alkylene group as generally defined above. 1- "C4 alkyl" should be interpreted accordingly.

[0036] As used herein, the term "C1-C6 alkoxy" refers to a b OR a O-group, where R a and R b Each is C1-C6 alkylene as generally defined above. The term "C1-C4 alkoxy" should be interpreted accordingly.

[0037] As used herein, the term "C1-C6 alkoxycarbonyl C1-C6 alkoxy" refers to a b OC(O)R a O-group, where R a and R b All are C1-C6 alkylene groups as generally defined above.

[0038] As used herein, the term "C3-C6 cycloalkyl" refers to a group that is a monocyclic saturated ring system and contains 3 to 6 carbon atoms. The terms "C3-C5 cycloalkyl" and "C3-C4 cycloalkyl" should be interpreted accordingly. Examples of C3-C6 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0039] As used herein, the term "C3-C6 cycloalkylaminocarbonyl" refers to a C3-C6 cycloalkyl ring attached to the rest of the molecule through a -NHC(O)- linker.

[0040] As used herein, the term "benzyloxy" refers to a benzyl ring attached to the rest of the molecule through an oxygen atom.

[0041] Unless otherwise described, otherwise, as used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic group comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur. In some cases, the heteroaryl moiety can be attached to the rest of the molecule by the nitrogen atom in the heteroaryl ring. In other cases, the heteroaryl moiety can be attached to the rest of the molecule by the carbon atom in the heteroaryl ring. The example of heteroaryl includes but is not limited to furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl or pyridyl.

[0042] As used herein, the term "heterocyclic group" refers to a stable 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms, wherein the heteroatoms are individually selected from nitrogen, oxygen and sulfur. The heterocyclic group can be bonded to the rest of the molecule via a carbon atom or a heteroatom. The example of a heterocyclic group includes but is not limited to aziridine, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolanyl, dithiolanyl and thiazolidinyl.

[0043] As used herein, the term "C1-C6 alkylcarbonyl" refers to a group having the formula -C(O)R a A group in which R a is a C1-C6 alkyl group as generally defined above. Examples of C1-C6 alkylcarbonyl groups include, but are not limited to, acetyl.

[0044] As used herein, the term "C1-C6 alkoxycarbonyl" refers to a group having the formula -C(O)OR a A group in which R a is a C1-C6 alkyl group as generally defined above.

[0045] As used herein, the term "C1-C6 alkylamino" refers to a a NH-group, where R a is a C1-C6 alkyl group as generally defined above.

[0046] As used herein, the term "C1-C6 alkylaminocarbonyl" refers to a group having the formula -C(O)NHR a A group in which R a is a C1-C6 alkyl group as generally defined above.

[0047] As used herein, the term "C1-C6 alkylcarbonylamino" refers to a a C(O)NH-, where R a is a C1-C6 alkyl group as generally defined above.

[0048] As used herein, the term "C1-C6 alkoxy C1-C6 alkylaminocarbonyl" refers to a a OR b NHC(O)-, where R a is a C1-C6 alkyl group, R a is C1-C6 alkylene as generally defined above.

[0049] As used herein, the term "C1-C6 alkoxy C1-C6 alkylcarbonylamino" refers to a a OR b C(O)NH-, where R a is a C1-C6 alkyl group, R a is C1-C6 alkylene as generally defined above.

[0050] As used herein, the term "C2-C6 alkenylcarbonylamino" refers to a a OC(O)NH-, where R a is a C1-C6 alkylene group as generally defined above.

[0051] As used herein, the term "N,N-di(C1-C4 alkyl)amino" refers to a a )(R b )NH-, where R a and R b Each is individually a C1-C4 alkyl group as generally defined above.

[0052] As used herein, the term "N,N-di(C1-C4 alkyl)aminocarbonyl" refers to a group having the formula -C(O)N(R a )(R b ) group, wherein R a and R b Each individually is a C1-C4 alkyl group as generally defined above. The term "N,N-di(C1-C3 alkyl)aminocarbonyl" should be interpreted accordingly.

[0053] As used herein, the term "C1-C6 alkylsulfanyl" refers to a alkylsulfanyl group having the formula -SR a A group in which R a is a C1-C6 alkyl group as generally defined above. The terms "C1-C4 alkylsulfanyl" and "C1-C3 alkylsulfanyl" should be interpreted accordingly. Examples of C1-C6 alkylsulfanyl groups include, but are not limited to, methylsulfanyl.

[0054] As used herein, the term "C1-C6 alkylsulfinyl" refers to a group having the formula -S(O)R a A group in which R a is a C1-C6 alkyl group as generally defined above. The terms "C1-C4 alkylsulfinyl" and "C1-C3 alkylsulfinyl" should be interpreted accordingly. Examples of C1-C6 alkylsulfinyl groups include, but are not limited to, methylsulfinyl.

[0055] As used herein, the term "C1-C6 alkylsulfonyl" refers to a group having the formula -S(O)2R a A group in which R a is a C1-C6 alkyl group as generally defined above. The terms "C1-C4 alkylsulfonyl" and "C1-C3 alkylsulfonyl" should be interpreted accordingly. Examples of C1-C6 alkylsulfonyl groups include, but are not limited to, methylsulfonyl.

[0056] As used herein, the term "C1-C6 alkylsulfonylamino" refers to a alkylsulfonylamino group having the formula -NHS(O)2R a A group in which R a is a C1-C6 alkyl group as generally defined above.

[0057] The presence of one or more possible stereogenic elements in a compound of formula (I) means that the compound may exist in optical isomeric forms (i.e., enantiomers or diastereomeric forms). Also, as a result of restricted rotation around a single bond, atropisomers may exist. Formula (I) is intended to include all those possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms and mixtures thereof of compounds of formula (I). Similarly, formula (I) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms of compounds of formula (I).

[0058] In each case, the compounds of formula (I) according to the invention are in free form, oxidized form (such as N-oxides) or salt form (e.g., agronomically acceptable salt forms). Preferred are salts that the compounds of formula (I) can form with: amines, including primary, secondary and tertiary amines (e.g., ammonia, dimethylamine and triethylamine); alkali metal bases and alkaline earth metal bases, transition metal bases or quaternary ammonium bases.

[0059] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. They are described, for example, by A. Albini and S. Pietra in the book "Heterocyclic N-oxides", CRC Press, Boca Raton (1991).

[0060] The following list provides information on the substituents R of compounds having formula (I): 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , and R 10 For any of these substituents, any definition given below may be combined with any definition of any other substituent given below or elsewhere in this document.

[0061] 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 1is C1-C3 alkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy C1-C3 alkyl, or C3-C4 cycloalkyl. Still more preferably, R 1 is methyl, ethyl, n-propyl, methoxy, 2-methoxyethyl, allyl and prop-2-ynyl. Even more preferably, R 1 In one embodiment, R 1 It is ethyl.

[0062] R 2 is phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms independently selected from N, O and S, and wherein each phenyl and heteroaryl moiety may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 7 The group represented is substituted.

[0063] 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 independently selected from N, O and S, and wherein each phenyl and heteroaryl moiety may be optionally substituted by 1, 2 or 3 residues which may be the same or different and are represented by R 7 The group represented is substituted.

[0064] 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 independently selected from N and O, and wherein each phenyl and heteroaryl moiety may be optionally substituted by 1, 2 or 3 residues which may be the same or different and are represented by R 7 The group represented is substituted.

[0065] Still 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 independently selected from N and O, and wherein each phenyl and heteroaryl moiety may be optionally replaced by 1 or 2 residues which may be the same or different and are represented by R 7 The group represented is substituted.

[0066] Even more preferably, R 2 is optionally replaced by 1 or 2 which may be the same or different from R 7 In one embodiment, R 2 It is 3,4-dichlorophenyl or 3,4-difluorophenyl, preferably 3,4-dichlorophenyl.

[0067] R 4is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1, 2 or 3 nitrogen atoms, and wherein the heteroaryl moiety is attached to the rest of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl moiety may each be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 9 The group represented is substituted.

[0068] Preferably, R 4 is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1, 2 or 3 nitrogen atoms, and wherein the heteroaryl moiety is attached to the rest of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl moiety may each be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are represented by R 9 The group represented is substituted.

[0069] More preferably, R 4 is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 2 or 3 nitrogen atoms, and wherein the heteroaryl moiety is attached to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl moiety may each be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are represented by R 9 The group represented is substituted.

[0070] Still more preferably, R 4 is pyrazolyl, imidazolyl, triazolyl, wherein any of the pyrazolyl, imidazolyl and triazolyl moieties may each be optionally replaced by 1, 2 or 3 residues which may be the same or different and are represented by R 9 The group represented is substituted.

[0071] In one set of embodiments, R 4 is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 2 nitrogen atoms, and wherein the heteroaryl moiety is attached to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl ring is optionally substituted by 3 R 9 The group represented by 9The group is selected from formyl, cyano, nitro, hydroxyl, 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 C1-C6 alkylsulfonylamino, 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 R 9 The groups together with the carbon atom to which they are attached may form a phenyl ring, wherein the resulting phenyl moiety may be optionally substituted with a single R 10 Group substitution.

[0072] In another set of embodiments, R 4 is pyrazolyl, triazolyl or indazolyl, wherein each moiety is optionally substituted by one or two substituents selected from the group consisting of 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. Preferably, R 4 is pyrazolyl optionally substituted by one or two substituents selected from the group consisting of 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 a single substituent selected from halogen and C1-C3 haloalkyl, preferably chloro and trifluoromethyl.

[0073] In a particularly preferred group of embodiments, R 43-(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 group of embodiments is wherein R 4 Examples are 3-(trifluoromethyl)pyrazol-1-yl, 3-chloropyrazol-1-yl or 4-chloropyrazol-1-yl.

[0074] R 5 is hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl. 5 is 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. Still more preferably, R 5 is hydrogen or C1-C3 alkyl. Even more preferably, R 5 It is a C1-C3 alkyl group, and preferably a methyl group.

[0075] R 7 It 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 alkylsulfonyl, C1-C6 alkylsulfonylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, or N,N-di(C1-C4 alkyl)aminocarbonyl.

[0076] Preferably, R 7It 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 alkylsulfonyl, C1-C4 alkylsulfonylamino, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, or N,N-di(C1-C3 alkyl)aminocarbonyl.

[0077] More preferably, R 7 It is 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 alkylsulfonyl, C1-C3 alkylsulfonylamino, C1-C3 alkylcarbonyl, C1-C3 alkoxycarbonyl, C1-C3 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, or N,N-di(C1-C3 alkyl)aminocarbonyl.

[0078] Still 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.

[0079] In one set of embodiments, R 7 is cyano, nitro, or halogen, preferably halogen, and more preferably chlorine or fluorine.

[0080] R 9is formyl, cyano, nitro, hydroxyl, 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 alkylsulfonylamino, 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

[0081] Any two adjacent R 9 The groups together with the carbon atoms 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 replaced by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 10 or

[0082] Any two adjacent R 9 The groups together with the carbon atoms 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 independently selected from N, O and S, and wherein the heteroaryl moiety may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are composed of R 10 or

[0083] Any two adjacent R 9 The 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 a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are composed of R 10 The group represented is substituted.

[0084] Preferably, R 9is formyl, cyano, nitro, hydroxyl, 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 alkylsulfonylamino, 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

[0085] Any two adjacent R 9 The groups together with the carbon atoms 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 replaced by 1, 2 or 3 residues which may be the same or different and which are represented by R 10 or

[0086] Any two adjacent R 9 The groups together with the carbon atoms 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 independently selected from N, O and S, and wherein the heteroaryl moiety may be optionally substituted by 1, 2 or 3 which may be the same or different and are composed of R 10 or

[0087] Any two adjacent R 9 The 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 a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are composed of R 10 The group represented is substituted.

[0088] More preferably, R 9is formyl, cyano, nitro, hydroxyl, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C2-C4 alkenyloxy, cyano C1-C3 alkoxy, C1-C3 alkoxy C1-C3 alkyl, C1-C3 alkoxy C1-C3 alkoxy, C1-C3 alkoxycarbonyl C1-C3 alkoxy, C1-C3 alkoxycarbonyl, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylsulfonylamino, C1-C3 alkylcarbonyl, C1-C3 alkylaminocarbonyl, C1-C3 alkylcarbonylamino, C1-C3 alkylamino, C1-C3 alkoxy C1-C3 alkylaminocarbonyl, C1-C3 alkoxy C1-C3 alkylcarbonylamino, C2-C4 alkenylcarbonylamino, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)amino, N,N-di(C1-C3 alkyl)aminocarbonyl, or benzyloxy; or

[0089] Any two adjacent R 9 The groups together with the carbon atoms 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 replaced by 1 or 2 residues which may be the same or different and are represented by R 10 or

[0090] Any two adjacent R 9 The groups together with the carbon atoms 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 independently selected from N, O and S, and wherein the heteroaryl moiety may be optionally substituted by 1 or 2 R which may be the same or different 10 or

[0091] Any two adjacent R 9 The 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 a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted by 1 or 2 residues which may be the same or different and which are composed of R 10 The group represented is substituted.

[0092] Even more preferably, R 9is formyl, cyano, nitro, halogen, C1-C4 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C2 haloalkoxy, C2-C3 alkenyloxy, cyano C1-C2 alkoxy, C1-C3 alkoxy C1-C3 alkyl, C1-C3 alkoxy C1-C3 alkoxy, C1-C3 alkoxycarbonyl C1-C3 alkoxy, C1-C3 alkoxycarbonyl, C1-C3 Alkylsulfanyl, C1-C3 alkylsulfonyl, C1-C3 alkylcarbonyl, C1-C3 alkylaminocarbonyl, C1-C3 alkylcarbonylamino, C1-C3 alkylamino, C1-C3 alkoxy C1-C3 alkylaminocarbonyl, C1-C2 alkoxy C1-C2 alkylcarbonylamino, C3-C4 alkenylcarbonylamino, C3-C4 cycloalkyl, or N,N-di(C1-C3 alkyl)amino; or

[0093] Any two adjacent R 9 The groups together with the carbon atoms to which they are attached may form a C5-C6 cycloalkyl ring or a phenyl ring, wherein the C5-C6 cycloalkyl and phenyl portions may be optionally replaced by a single R 10 group substitution; or

[0094] Any two adjacent R 9 The groups together with the carbon atom to which they are attached may form a 6-membered heteroaryl ring, wherein the heteroaryl moiety is a 6-membered aromatic ring containing a single nitrogen atom, and wherein the heteroaryl moiety may be optionally substituted by a single R 10 group substitution; or

[0095] Any two adjacent R 9 The 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 a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted with a single R 10 Group substitution.

[0096] 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 R 9 The groups together with the carbon atom to which they are attached may form a 10 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 R 9The groups together with the carbon atom to which they are attached may form a 10 A phenyl ring substituted with a group.

[0097] R 10 is halogen, C1-C3 alkyl, or C1-C3 alkoxy. 10 is halogen or C1-C3 alkoxy. More preferably, R 10 is halogen or methoxy. Even more preferably, R 10 is fluorine or methoxy.

[0098] Among the compounds of formula (I) according to the present invention, preferably:

[0099] R 1 It is ethyl;

[0100] R 2 is 3,4-dichlorophenyl or 3,4-difluorophenyl;

[0101] R 4 is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 2 or 3 nitrogen atoms, and wherein the heteroaryl moiety is attached to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl moiety may each be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are represented by R 9 The group represented by is substituted;

[0102] R 5 It is methyl;

[0103] R 9 is formyl, cyano, nitro, hydroxyl, 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 alkylsulfonylamino, 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

[0104] Any two adjacent R 9The groups together with the carbon atoms 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 replaced by 1, 2 or 3 residues which may be the same or different and which are represented by R 10 or

[0105] Any two adjacent R 9 The groups together with the carbon atoms 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 independently selected from N, O and S, and wherein the heteroaryl moiety may be optionally substituted by 1, 2 or 3 which may be the same or different and are composed of R 10 or

[0106] Any two adjacent R 9 The 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 a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are composed of R 10 The group represented by is substituted;

[0107] R 10 It is halogen or C1-C3 alkoxy.

[0108] In another set of embodiments,

[0109] R 1 It is ethyl;

[0110] R 2 It is 3,4-dichlorophenyl;

[0111] R 4 is 3-(trifluoromethyl)pyrazol-1-yl, 3-chloropyrazol-1-yl or 4-chloropyrazol-1-yl; and

[0112] R 5 It's methyl.

[0113] The compounds of the present invention can be prepared as shown in the following schemes, wherein, unless otherwise stated, the definition of each variable is as defined above for compounds of formula (I). The following describes a general method for producing compounds of formula (I). Unless otherwise stated in the text, R 1 , R 2 , R 4 and R 5is as defined above. The starting materials for preparing the compounds of the present invention can be purchased from common commodity suppliers or can be prepared by known methods. The starting materials and intermediates can be purified by prior art methods (such as chromatography, crystallization, distillation and filtration) before being used in the next step.

[0114] Compounds of formula (I) according to the present invention can be prepared from compounds of formula (A) as shown in Scheme 1 below.

[0115] Scenario 1:

[0116]

[0117] Where R 4 Compounds with formula (I) as defined above can be prepared by compounds with formula (A) wherein Y is I (iodine) via Ullmann type cross-coupling reaction. Typically, the reaction is carried out by reacting a compound with formula (A) with a cyclic NH-heterocycle (such as pyrazole) in the presence of a copper salt (such as copper iodide (I)) and a ligand (such as N, N'-bis (2,6-dimethoxyphenyl) oxamide), in the presence of a base (such as potassium carbonate), in a suitable organic solvent (such as dimethyl sulfoxide) at high temperature. This is shown in the above scheme 1.

[0118] Scenario 2:

[0119]

[0120] The compound of formula (A) wherein Y is I (iodine) can be prepared by reacting a compound of formula (B) wherein R 3 C1-C6 alkyl) in a suitable solvent (such as methanol, ethanol, dichloromethane, chloroform, ethyl acetate or tetrahydrofuran) and an optional cosolvent (such as water) with a suitable base (such as sodium hydroxide or lithium hydroxide) or with a suitable acid (such as trifluoroacetic acid, hydrochloric acid, formic acid or sulfuric acid) to prepare. This is shown in Scheme 2 above.

[0121] Scenario 3:

[0122]

[0123] Compounds of formula (B) wherein Y is I (iodine) can be prepared by treating a compound of formula (C) with a suitable halogenating agent (such as N-iodosuccinimide) in a suitable solvent (such as acetonitrile or trifluoroacetic acid). This is shown in Scheme 3 above.

[0124] Solution 4:

[0125]

[0126] Compounds of formula (C) can be prepared by reacting compounds of formula (E) with compounds of formula (F) in the absence of solvent at elevated temperature (e.g. 120° C.). Compounds of formula E are commercially available or can be prepared by methods familiar to those skilled in the art. This is shown in Scheme 4 above.

[0127] Solution 5:

[0128]

[0129] Compounds of formula (F) can be prepared by reaction of a β-ketoester of formula (G) with an amine salt. Amine salts can be prepared in situ by acidifying an amine of formula (H) with a suitable acid such as acetic acid. These amine salts can then be dried in an acid such as acetic acid and a drying agent such as The compound of formula (G) is reacted with a compound of formula (H) in the presence of a molecular sieve (e.g., toluene) in a suitable solvent (e.g., toluene). The compound of formula (G) is commercially available or can be prepared using the conditions described below. The compound of formula (H) is commercially available or can be prepared by methods familiar to those skilled in the art. This is shown in Scheme 5 above.

[0130] Solution 6:

[0131]

[0132] Compounds of formula (G) can be prepared by treating a ketone of formula (i) with a base (such as sodium hydride) in the presence of a dialkyl carbonate (such as dimethyl carbonate) of formula (J). Compounds of formula (i) and formula (J) are commercially available or can be prepared by methods familiar to those skilled in the art. This is shown in Scheme 6 above.

[0133] The present invention further provides a method for controlling weeds at a site, the method comprising applying a composition comprising a compound of formula (I) to the site in an amount of weed control. In addition, the present invention may further provide a method for selectively controlling weeds at a site including useful (crop) plants and weeds, wherein the method comprises applying a composition according to the present invention in an amount of weed control to the site. 'Control' means killing, reducing or delaying growth or preventing or reducing germination. It should be noted that the compounds of the present invention show greatly improved selectivity compared to known structurally similar compounds. Typically, the plants to be controlled are unwanted plants (weeds). 'Site' means the area where the plant is growing or will grow. Application can be applied to the site before and / or after emergence of crop plants. Some crop plants can inherently tolerate the herbicidal action of compounds with formula (I).

[0134] 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-emergence or post-emergence; seed dressing; application to the seed furrow; no-till application, etc.), the crop plants, one or more weeds to be controlled, the prevailing climatic conditions and other factors governed by the method of application, the time of application and the target crop. The compound of formula I according to the invention is usually applied at a rate of 10 g / ha to 2500 g / ha, especially 25 g / ha to 1000 g / ha, more especially 25 g / ha to 250 g / ha.

[0135] Application is usually carried out by spraying the composition, typically by means of a tractor-mounted sprayer for large areas, but other methods such as dusting (for powders), dripping or drenching may also be used.

[0136] The term "useful plants" is to be understood as also including useful plants which have been rendered tolerant to herbicides such as bromoxynil or 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 as a result of conventional methods of breeding or genetic engineering. Examples of crops which have been rendered tolerant to imidazolinones such as imazamox by conventional methods of breeding (mutagenesis) are Summer rapeseed (Canola). Examples of crops that have been rendered tolerant to herbicides or herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties sold under the trade name Roundup and Commercially available.

[0137] The term "useful plants" is to be understood as also including useful plants which have been transformed by the use of recombinant DNA techniques in such a way that they are able to synthesize one or more selectively acting toxins, as are known, for example, from toxigenic bacteria, in particular those of the genus Bacillus.

[0138] Examples of such plants are: (maize variety expressing CryIA(b) toxin); YieldGard (maize variety expressing CryIIIB(b1) toxin); YieldGard (maize varieties expressing CryIA(b) and CryIIIB(b1) toxins); (maize variety expressing Cry9(c) toxin); Herculex (maize variety expressing the CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate ammonium); NuCOTN (cotton variety expressing CryIA(c) toxin); Bollgard (cotton variety expressing CryIA(c) toxin); Bollgard (cotton varieties expressing CryIA (c) and CryIIA (b) toxins); (cotton varieties expressing VIP toxin); (potato variety, expressing CryIIIA toxin); GT Advantage (GA21 glyphosate tolerance trait), CB Advantage (Bt11 corn borer (CB) trait), RW (corn rootworm trait) and

[0139] Plant crops or their seed material can be both resistant to herbicides and at the same time resistant to insect feeding ("stacked" transgenic events). For example, seeds can have the ability to express an insecticidal Cry3 protein while being tolerant to glyphosate.

[0140] Crop plants are also to be understood as including those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (eg improved storage stability, higher nutritional value and improved flavor).

[0141] The compounds of formula (I) (or compositions comprising them) can be used to control unwanted plants (collectively referred to as 'weeds'). The weeds to be controlled may be monocotyledonous species, for example Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria, a) and Sorghum, and also dicotyledonous species, such as Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium.

[0142] The compounds of formula (I) can be used in unmodified form or preferably together with adjuvants conventionally used in the field of formulation to provide herbicidal compositions, using formulation adjuvants, such as carriers, solvents and surfactants (SAAs). Therefore, the present invention further provides a herbicidal composition comprising at least one compound of formula (I) and 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.

[0143] The herbicidal compositions generally comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds of formula I and 1 to 99.9% by weight of formulation adjuvants which preferably comprise 0 to 25% by weight of surface-active substances.

[0144] 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), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil suspensions (OF), oil-soluble liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), master drugs (TK), dispersible concentrates (DC), soluble powders (SP), wettable powders (WP) and soluble granules (SG). In any case, the formulation type selected will depend on the specific purpose envisioned and the physical, chemical and biological properties of the compound of formula (I).

[0145] 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 sulfate) or one or more water-soluble organic solids (such as polysaccharides) and optionally one or more wetting agents, one or more dispersants or mixtures of said agents to improve water dispersibility / water solubility. The mixture is then ground into a fine powder. Similar compositions can also be granulated to form water-soluble granules (SG).

[0146] 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 dispersants, and optionally one or more suspending agents to facilitate dispersion in a liquid. The mixture is then ground into a fine powder. Similar compositions can also be granulated to form water dispersible granules (WG).

[0147] Granules (GR) may be formed by granulating a mixture of a 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 agent) into a porous granular material such as pumice, attapulgite clay, Fuller's earth, kieselguhr, diatomaceous earth or corn cob meal, or by adsorbing the compound of formula (I) (or a solution thereof in a suitable agent) onto a hard core material such as sand, silicates, mineral carbonates, sulfates or phosphates and drying if necessary from preformed green particles. Agents commonly used to aid absorption or adsorption include solvents such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters and adhesives such as polyvinyl acetate, polyvinyl alcohol, dextrins, sugars and vegetable oils. One or more other additives (e.g., emulsifiers, wetting agents or dispersants) may also be included in the granules.

[0148] Dispersible concentrates (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 (for example to improve water dilution or to prevent crystallization in a spray tank).

[0149] Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) can be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifiers or a mixture of said agents). Suitable organic solvents for use in ECs 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 (such as C8-C 10 EC products emulsify spontaneously when added to water, producing an emulsion with sufficient stability to allow spray application by appropriate equipment.

[0150] The preparation of EWs involves obtaining a compound of formula (I) as a liquid (if it is not liquid at room temperature, it can be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in a suitable solvent), and then emulsifying the resulting liquid or solution into water containing one or more SAAs under high shear to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzene), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other suitable organic solvents having low solubility in water.

[0151] Microemulsions (ME) can be prepared by mixing water with a blend of one or more solvents and one or more SAAs to spontaneously produce a thermodynamically stable, isotropic liquid formulation. The compound of formula (I) is initially present in water or in a solvent / SAA blend. Suitable solvents for use in MEs include those described above for use in ECs or EWs. MEs can be oil-in-water systems or water-in-oil systems (which system is present can be determined by conductivity measurements) and can be suitable for mixing water-soluble pesticides and oil-soluble pesticides in the same formulation. MEs are suitable for dilution into water, remaining as microemulsions or forming conventional oil-in-water emulsions.

[0152] Suspension concentrates (SC) may include aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I). SC may be prepared by ball milling or bead milling a solid compound of formula (I) with one or more dispersants in a suitable medium to produce 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 rate of particle settling. Alternatively, a compound of formula (I) may be dry-milled and added to water containing the reagents described above to produce a desired final product.

[0153] Aerosol formulations comprise a 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 water-miscible liquid such as n-propanol) to provide a composition for use in a non-pressurized hand-operated spray pump.

[0154] Capsule suspensions (CS) can be prepared in a similar manner to the preparation of EW formulations, but with an additional polymerization stage, to obtain an aqueous dispersion of oil droplets, each of which is wrapped by a polymer shell and contains a compound of formula (I) and optionally a carrier or diluent for the oil droplet. The polymer shell can be produced by an interfacial polycondensation reaction or by a coacervation procedure. These compositions can provide controlled release of compounds of formula (I) and they can be used for seed treatment. Compounds of formula (I) can also be formulated in a biodegradable polymer matrix to provide slow, controlled release of the compound.

[0155] The composition may include one or more additives to improve the biological performance of the composition, for example by improving wettability, retention or distribution on a surface; rain resistance on a treated surface; or absorption or mobility of a compound of formula (I). Such additives include surfactants (SAAs), oil-based spray additives such as certain mineral oils or natural vegetable oils (such as soybean and rapeseed oils), modified vegetable oils (such as methylated rapeseed oil (MRSO)), and blends of these with other bioenhancement adjuvants (ingredients that can assist or modify the action of a compound of formula (I)).

[0156] The wetting agent, dispersant and emulsifier may be a cationic type, anionic type, amphoteric type or nonionic type SAA.

[0157] Suitable cationic-type SAAs include quaternary ammonium compounds (eg, cetyltrimethylammonium bromide), imidazolines, and amine salts.

[0158] Suitable anionic SAAs include alkali metal salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (e.g. sodium lauryl sulfate), salts of sulfonated aromatic compounds (e.g. sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalenesulfonate and mixtures of sodium di-isopropyl-naphthalenesulfonate and sodium tri-isopropyl-naphthalenesulfonate), ether sulfates, alcohol ether sulfates (e.g. sodium laureth-3-sulfate), ether carboxylates (e.g. sodium laureth-3-carboxylate), phosphates (products from the reaction of one or more fatty alcohols with phosphoric acid (mainly monoesters) or with phosphorus pentoxide (mainly diesters), for example the reaction of lauryl alcohol with tetraphosphoric acid; additionally, these products may be ethoxylated), sulfosuccinamates, paraffin or olefin sulfonates, taurates, lignin sulfonates and phosphates / sulfates of tristyrylphenol.

[0159] Suitable amphoteric SAAs include betaines, propionates and glycinates. Suitable nonionic SAAs include condensation products 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 with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long-chain fatty acids or hexitol anhydrides; condensation products of the partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; monoesters (such as fatty acid polyethylene glycol esters); amine oxides (such as lauryl dimethylamine oxide); lecithin and sorbitan and its esters, alkyl polyglycosides and tristyrylphenol. Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinyl pyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

[0160] The compounds of the present invention may also be used in admixture 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), bennitroprop-butyl, ametryn, amitriptyline, aminopyralid, cypermethrin, atrazine, flubutyric acid, quinquitrione, bensulfuron-methyl (including bensulfuron-methyl), bentazone, flupyralid, bialaphos, bispyribac-butyl, bispyribac-sodium, bixlozone, bromomethalin, herbicide, bromoxynil, butachlor, flupyralid, mesotrione (including mesotrione-ethyl), chlorsulfuron (including chlorsulfuron-methyl), chlorsulfuron (including chlorsulfuron-ethyl), chlorotoluron, chlorsulfuron, cyclohexane. cypermethrin, chlorpyrifos, clethodim, clodinafop-butyl (including clodinafop-butyl), clomazone, clopyralid, cyclopyranil, cyclopyrimorate, cyprosulfuron, cyhalofop-butyl (including cyhalofop-butyl-butyl), 2,4-D (including its choline salt and 2-ethylhexyl ester), 2,4-DB, betaine, dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloropropane, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), bischlorosulfuron, fluazifop-butyl, fluazifop-butyl, dimethoate, dimethoate-s-propyl, dioxopyritrione, dibromo Diquat, diuron, epyrifenacil, ethoflufenacil, oxadiazine (including epyrifenacil-ethyl), benzenesulfuron, benazole, fenquinotrione, tetrazoline, fluazifop-butyl, bispyribac, clofopyralid (including clofopyralid-benzyl), fluazifop-butyl (including fluazifop-butyl-butyl), fluazifop-butyl (including fluazifop-sodium), fluclofenac (including fluclofenac furfuryl), flufenacet, fluazifop-butyl ... Including fluroxypyr-meptyl), fluroxypyr-meptyl, fluazifop-butyl, foramsulfuron, glufosinate (including L-glufosinate and its ammonium salts), glyphosate (including its ammonium, isopropyl ammonium and potassium salts), fluazifop-butyl (including fluazifop-methyl), fluazifop-methyl (including fluazifop-methyl), hexazinone, hydantocidin, isoxazolidinone (including isoxazolidinone methyl), imazamox (including R-imazamox), imazapic, imazapic, imazapic, indoxazolidinone, indolepyralid (including indolepyralid), iodosulfuron-methyl (including iodosulfuron-methyl-sodium),Iofensulfuron (including iofensulfuron-sodium), ioboxynil, triazole oxadiazole, isoproturon, isoxathiapiprom, lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron-methyl), mesotrione, metamitron, pyraclostrobin, methiozolin, isopropylamine, sulfamethoxazole, metribuzin, metsulfuron-methyl, propamide, nicosulfuron, fluazifop, oxadiazine, oxasulfuron-methyl, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, bendisulfuron, picloram, pinoxabol, pretilachlor, primisulfuron-methyl, promethazine, propanil, oxadiazine, propyrisulfuron, propyrisulfuron, benzamid, prosulfuron, bispyribac, pyraflufen (including pyraflufen-ethyl), pyraflufen-butyl, ... Sulfurone, butylthiocarb, furansulfuron, cyproconazole, terbuthion, terbutaline, tetrafluralin, thiencarbazone, thifensulfuron, tiafenacil, tolpyralate, benpyrazone, trimethoprim, fluazifop, wild wheat chlorpyrifos, ether bensulfuron, bensulfuron (including bensulfuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), trifloxysulfuron, trifluralin, flufenac, triazosulfuron, 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-carboxylic acid ethyl esters, 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 carbonate, ethyl-2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridinyl]oxy]acetate, 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]-2-methoxy-acetic acid methyl ester, 6-chloro-4-(2,7-dioxo- methyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one, (2-fluorophenyl)methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)pyrimidine-4-carboxylate, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)pyrimidine-4-carboxylate and 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-carboxylic acid methyl ester.

[0161] The mixing partners of the compounds of formula (I) can also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, 19th edition, British Crop Protection Council, 2021. The mixing ratio of the compound of formula (I) to the mixing partner is preferably 1:100 to 1000:1.

[0162] These mixtures can advantageously be used in the abovementioned formulations (in this case, "active ingredient" relates to the corresponding mixture of the compound of formula (I) with the mixing partner).

[0163] 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 cloquintocet, cloquintocet (including cloquintocet-mexyl), cyclopropylsulfonamide, dichloropropene, oxadiazole (including oxadiazole ethyl), chlorpyrifos, fluazifop, oxadiazole, isoxadiazole (including isoxadiazole-ethyl), mefenpyr (including mefenpyr-butyl), metcamifen and oxadiazole.

[0164] Particularly preferred are mixtures of compounds of formula (I) with cyprosulfamide, isoxadifen-ethyl, clofonet-mexyl and / or sulfamethoxazole.

[0165] The safener of the compound of formula (I) may also be in the form of an ester or salt, as mentioned, for example, in The Pesticide Manual, 19th edition (BCPC), 2021. References to clofonethiol also apply to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as disclosed in WO 02 / 34048.

[0166] Preferably, the mixing ratio of compound of formula (I) to safener is from 100:1 to 1:10, in particular from 20:1 to 1:1.

[0167] Compounds of formula (I) are usually used in the form of agrochemical compositions and can be applied to crop areas or plants to be treated simultaneously or successively with other compounds. For example, these other compounds can be fertilizers or micronutrient donors or other preparations that affect plant growth. They can also be selective herbicides or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with other carriers, surfactants or adjuvants that are commonly used in the formulation field to promote application.

[0168] As used herein, the term "locus" means a place in or on which plants grow, or where seeds of cultivated plants are sown, or where seeds are to be placed in the soil. It includes soil, seeds and seedlings, as well as established vegetation.

[0169] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves, and fruits.

[0170] The term "plant propagation material" should be understood to mean the reproductive parts of a plant, such as seeds, which can be used for the propagation of a plant, and vegetative materials, such as cuttings or tubers (e.g., potatoes). For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants can be mentioned. Germinated plants and young plants that will be transplanted after germination from the soil or after emergence can also be mentioned. These young plants can be protected before transplanting by being treated completely or partially via dipping. Preferably, "plant propagation material" should be understood to mean a seed.

[0171] The pesticides mentioned here using their common names are known, for example, from “The Pesticide Manual”, 15th edition, British Crop Protection Council 2009.

[0172] Compounds with formula (I) can be used in unmodified form, or preferably, together with conventional adjuvants used in the formulation field. For this purpose, they can be conveniently formulated as emulsifiable concentrates, pastes that can be coated, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granules and also encapsulations, for example in polymeric substances, in a known manner. For the type of composition, according to the intended purpose and the environment at that time, the application method is selected, such as spraying, atomizing, dusting, sowing, coating or watering. Compositions can also contain other adjuvants, such as stabilizers, defoamers, viscosity modifiers, adhesives or tackifiers, and fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0173] Suitable carriers and adjuvants, for example for agricultural use, may be solid or liquid and are substances useful in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, adhesives or fertilizers. Such carriers are for example described in WO 97 / 33890.

[0174] The compounds of formula (I) are usually used in the form of compositions and can be applied to crop areas or plants to be treated simultaneously or successively with other compounds. For example, these other compounds can be fertilizers or micronutrient donors or other preparations that affect plant growth. They can also be selective herbicides or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with other carriers, surfactants or adjuvants that are commonly used in the field of formulations to promote application.

[0175] The compound of formula (I) can be the sole active ingredient of the composition, or it can be mixed with one or more additional active ingredients (such as pesticides, fungicides, synergists, herbicides or plant growth regulators) when appropriate. In some cases, the additional active ingredients can produce unexpected synergistic activity.

[0176] Typically, the formulation comprises 0.01% to 90% by weight of an active agent, 0% to 20% of an agriculturally acceptable surfactant and 10% to 99.99% of a solid or liquid formulation inert agent and one or more adjuvants, the active agent being at least composed of a compound with formula (I) together with components (B) and (C), and optionally other active agents (particularly microbicides or preservatives or the like). The concentrated form of the composition typically contains between about 2% and 80% by weight, preferably between about 5% and 70% of the active agent. The application form of the formulation can, for example, contain 0.01% to 20% by weight, preferably 0.01% to 5% by weight of the active agent. However, commercial products will preferably be formulated as concentrates, and end users will typically use diluted formulations.

[0177] The following table shows examples of individual compounds of formula (I) according to the invention:

[0178]

[0179] Table 1: Individual compounds of formula (I) according to the invention

[0180]

[0181]

[0182] Table A-1 Provided are 26 compounds A-1.001 to A.1.026 having formula (I), wherein R 1 , R 2 , R 4 and R 5 As defined in Table 1.

[0183] Preparation Examples

[0184]

[0185] The active ingredient is mixed thoroughly with the adjuvant and the mixture is ground thoroughly in a suitable grinder to provide a wettable powder which can be diluted with water to give a suspension of the desired concentration.

[0186]

[0187] The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable grinder to provide a dust that can be used directly for seed treatment.

[0188] Emulsifiable concentrates

[0189]

[0190] Emulsions of any desired dilution which can be used for plant protection can be obtained from these concentrates by dilution with water.

[0191]

[0192] Ready-to-use dusts are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. Such dusts can also be used for dry seed dressing of seeds.

[0193] Extruder Granules

[0194]

[0195] The active ingredient is mixed with the auxiliary agent and ground, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0196] Coated granules

[0197] Active ingredient [compound of formula (I)] 8%

[0198] Polyethylene glycol (molecular weight 200) 3%

[0199] Kaolin 89%

[0200] The finely ground active ingredient is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

[0201] Suspension concentrates

[0202]

[0203] The finely ground active ingredients are intimately mixed with adjuvants to give suspension concentrates from which suspension concentrates of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated and protected from microbial infestation by spraying, pouring or immersion.

[0204] Flowable concentrate for seed treatment

[0205]

[0206] The finely ground active ingredients are intimately mixed with adjuvants to give suspension concentrates from which suspension concentrates of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated and protected from microbial infestation by spraying, pouring or immersion.

[0207] Extended-release capsule suspension

[0208] 28 parts of a combination of compounds of formula (I) are 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 parts of a defoamer and 51.6 parts of water until the desired particle size is reached. To this emulsion are added 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water. The mixture is stirred until the polymerization reaction is complete. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% of active ingredient. The diameter of the medium capsules is 8-15 microns. The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for this purpose.

[0209] Examples

[0210] The following non-limiting examples provide specific synthetic methods for representative compounds of the present invention (as mentioned in Table 2 below).

[0211] List of abbreviations

[0212] brs = broad singlet, °C = degrees Celsius, d = doublet, dd = doublet of doublet, DMSO = dimethyl sulfoxide, HPLC = high performance liquid chromatography, M = molar, m = multimodal, MHz = megahertz, mL = milliliters, q = quartet, s = singlet, t = triplet, THF = tetrahydrofuran.

[0213] 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)

[0214] Step 1: Synthesis of methyl 3-(3,4-dichlorophenyl)-3-oxo-propionate

[0215]

[0216] To the stirred solution of 1-(3,4-dichlorophenyl) ethyl ketone (5.00g, 26.5mmol) and dimethyl carbonate (40mL, 466mmol) cooled to 0°C under nitrogen, sodium hydride (3.17g, 79.5mmol, 60% by mass) was added in batches. The reaction mixture was warmed to room temperature and stirred for 16 hours. After overnight, the reaction mixture became a solid paste that could not be stirred. More dimethyl carbonate (10mL) was added in an attempt to produce a flowing slurry for quenching. Under nitrogen, the reaction mixture was cooled to 0°C and quenched by adding water (25mL). The reaction mixture was acidified to pH 3 by adding aqueous hydrochloric acid solution (2M), and then extracted with ethyl acetate. The organic extract was dried over magnesium sulfate and evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica using a gradient of 0-15% ethyl acetate in isohexane as eluent to give 3-(3,4-dichlorophenyl)-3-oxo-propionic acid methyl ester (mixture of tautomers) as a colourless liquid.

[0217] Enol: 1 H NMR (400 MHz, chloroform) δ=12.47 (s, 1H), 7.87 (d, 1H), 7.59 (m, 3H), 7.49 (d, 1H), 5.65 (s, 1H), 3.82 (s, 3H)

[0218] ketone: 1 H NMR (400 MHz, chloroform) δ = 8.03 (d, 1H), 7.77 (m, 1H), 7.58 (d, 2H), 3.97 (s, 2H), 3.76 (s, 3H).

[0219] Step 2: Synthesis of methyl (Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoate

[0220]

[0221] To a stirred solution of ethylamine (2M in THF) (12.2 mL, 24.34 mmol) at 0°C was added acetic acid (1.39 mL, 24.3 mmol) dropwise. The mixture was allowed to warm to room temperature and stirred for 1 hour, then evaporated to dryness under reduced pressure to give ethylammonium acetate (2.55 g, 24.3 mmol). Ethylammonium acetate (2.55 g, 24.3 mmol) was added to a solution of methyl 3-(3,4-dichlorophenyl)-3-oxo-propanoate (2.00 g, 8.09 mmol) in toluene (20 mL), followed by the addition of acetic acid (0.46 mL, 8.09 mmol) and powdered Molecular sieves. The reaction mixture was heated under reflux for 18 hours. The cooled reaction mixture was diluted with ethyl acetate, filtered and washed with saturated sodium bicarbonate aqueous solution. The phases were separated and the aqueous phase was extracted with ethyl acetate (x3). The combined organic extracts were washed with brine, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The crude residue was purified by silica gel flash chromatography using ethyl acetate with a gradient of 0-10% in isohexane as eluent to obtain (Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoic acid methyl ester as a light yellow oil. 1 HNMR (400 MHz, chloroform) δ = 8.37 (br s, 1H), 7.48 (d, 1H), 7.46 (d, 1H), 7.20 (m, 1H), 4.55 (s, 1H), 3.68 (s, 3H), 3.07 (m, 2H), 1.13-1.09 (m, 3H).

[0222] Step 3: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylate

[0223]

[0224] (Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoic acid methyl ester was added under nitrogen

[0225] The stirring mixture of (1.50g, 5.5mmol) and 2,2,6-trimethyl-1,3-dioxane-4-one (0.82g, 5.5mmol) was heated at 120 ° C for 3 hours. The cooled reaction mixture was evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 0-10% methanol in dichloromethane as eluent to obtain 2- (3,4-dichlorophenyl) -1-ethyl -6-methyl -4-oxo - pyridine -3-carboxylic acid methyl esters as off-white solids. 1 H NMR (400 MHz, chloroform) δ = 7.56 (d, 1H), 7.50 (d, 1H), 7.24 (m, 1H), 6.41 (s, 1H), 3.72 (q, 2H), 3.55 (s, 3H), 2.42 (s, 3H), 1.13 (t, 3H).

[0226] Step 4: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxo-pyridine-3-carboxylic acid methyl ester

[0227]

[0228] At room temperature and under nitrogen, 1-iodopyrrolidine-2,5-dione (3.70g, 16.5mmol) is added to a solution of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylic acid methyl esters (5.60g, 16.5mmol) in acetonitrile (56.0mL), followed by 2,2,2-trifluoroacetic acid (0.564g, 0.381mL, 4.94mmol). The reaction mixture is heated at 80 ° C for 36 hours, and then stirred at room temperature for 48 hours. The reaction mixture is quenched by adding saturated sodium bicarbonate aqueous solution (200mL) and extracted with dichloromethane (x3). The combined organic extracts are washed with saturated sodium thiosulfate solution, then washed with brine, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 0-100% ethyl acetate in cyclohexane as eluent to give 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxo-pyridine-3-carboxylic acid methyl ester as a white solid. 1 HNMR (400 MHz, chloroform) δ = 7.57 (d, 1H), 7.49 (d, 1H), 7.23 (m, 1H), 3.89 (q, 2H), 3.57 (s, 3H), 2.88 (s, 3H), 1.17 (t, 3H).

[0229] Step 5: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxo-pyridine-3-carboxylic acid

[0230]

[0231] To a solution of 2- (3,4- dichlorophenyl) -1- ethyl -5- iodo -6- methyl -4- oxo - pyridine -3- carboxylic acid methyl esters (12.60g, 27.0mmol) in methanol (113mL), a solution of lithium hydroxide (2.59g, 108mmol) in water (31.5mL) was added. The resulting white suspension was heated at 80 ° C for 2 hours, and then allowed to stand at room temperature for 18 hours. The cooled reaction mixture was acidified to pH 1 by adding aqueous hydrogen chloride solution (2M). The resulting white precipitate was collected by filtration, washed with water and air dried to obtain 2- (3,4- dichlorophenyl) -1- ethyl -5- iodo -6- methyl -4- oxo - pyridine -3- carboxylic acid as a white solid. 1 H NMR (500 MHz, chloroform) δ = 16.06 (brs, 1H), 7.60 (d, 1H), 7.34 (d, 1H), 7.10 (dd, 1H), 4.04-3.99 (m, 2H), 2.99 (s, 3H), 1.23 (t, 3H).

[0232] Step 6: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-[3-(trifluoromethyl)pyrazol-1-yl]pyridine-3-carboxylic acid

[0233]

[0234] A mixture of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxo-pyridine-3-carboxylic acid (0.25g, 0.553mmol), 3-(trifluoromethyl)-1H-pyrazole (0.27g, 1.99mmol), copper (I) iodide (0.106g, 0.553mmol), N, N'-bis(2,6-dimethoxyphenyl)oxamide (0.399g, 1.11mmol) and potassium carbonate (0.232g, 1.66mmol) was purged with nitrogen (x3), and then dimethyl sulfoxide (3.75mL) was added. The reaction mixture was heated at 120 ° C for 18 hours under stirring. The cooled reaction mixture was poured into water and diluted with ether. The aqueous phase was acidified to pH 1 by adding aqueous hydrogen chloride solution (2M). The brown solid precipitate was removed by filtration, and the organic phase was washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The crude residue was purified by mass directed reverse phase HPLC to give 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-[3-(trifluoromethyl)pyrazol-1-yl]pyridine-3-carboxylic acid as a white solid. 1 HNMR (400 MHz, chloroform) δ = 7.85-7.80 (m, 1H), 7.62 (d, 1H), 7.38 (d, 1H), 7.13 (dd, 1H), 6.79 (d, 1H), 3.95 (q, 2H), 2.41 (s, 3H), 1.27 (t, 3H).

[0235] 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)

[0236]

[0237] A mixture of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxo-pyridine-3-carboxylic acid (0.250g, 0.553mmol), 3-chloro-1H-pyrazole (0.204g, 1.99mmol), copper (I) iodide (0.106g, 0.553mmol), N, N'-bis (2,6-dimethoxyphenyl) oxamide (0.399g, 1.11mmol) and potassium carbonate (0.232g, 1.66mmol) was purged with nitrogen (x3), and then DMSO (3.75mL) was added. The reaction mixture was heated at 120 ° C for 18 hours. The cooled reaction mixture was poured into water and diluted with ether. The aqueous phase was acidified to pH 1 by adding aqueous hydrogen chloride solution (2M). The brown solid precipitate was removed by filtration, and the organic phase was washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The crude residue was purified by mass directed reverse phase HPLC to give 5-(3-chloropyrazol-1-yl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylic acid as a white solid. 1 H NMR (400 MHz, chloroform) δ = 7.67 (d, 1H), 7.62 (d, 1H), 7.37 (d, 1H), 7.13 (dd, 1H), 6.47 (d, 1H), 3.95 (q, 2H), 2.47 (s, 3H), 1.26 (t, 3H).

[0238] 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)

[0239]

[0240] 5-(3-Chloropyrazol-1-yl)-2-(3,4-difluorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylic acid was prepared as for 5-(3-chloropyrazol-1-yl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylic acid from 3',4'-difluoroacetophenone following the 6-step procedure described herein. 1 H NMR (400 MHz, chloroform) δ = 7.68 (d, 1H), 7.35 (td, 1H), 7.13 (ddd, 1H), 7.04-6.98 (m, 1H), 6.47 (d, 1H), 3.96 (q, 2H), 2.47 (s, 3H), 1.26 (t, 3H).

[0241] Throughout this specification, temperatures are given in degrees Celsius (° C.) and “mp” means melting point.

[0242] Table 2: Selected compounds according to the invention 1 H NMR data.

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254] Biological Examples

[0255] Seeds of various test species (Ipomoea hederacea (IPOHE), Setariafaberi (SETFA), Zea mays (ZEAMX), Echinochloa crus-galli (ECHCG), Amaranthus palmeri (AMAPA), Amaranthus retoflexus (AMARE)) were sown in standard soil in pots. After 8 days of cultivation under controlled conditions in a greenhouse (at 24°C / 16°C, day / night; 14 h light; 65% humidity), the plants were sprayed with an aqueous spray solution derived from a formulation of the technical grade active ingredient in an acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5). Unless otherwise stated, the compounds were applied at 1000 g / ha. These test plants were then grown in a greenhouse under controlled conditions in a greenhouse (at 24°C / 16°C, day / night; 14 hours of light; 65% humidity) and watered twice a day. After 13 days, the percentage of damage to the plants caused by the test was evaluated. 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).

[0256] Table B1: Pre-emergence test

[0257]

[0258] *Data at 250g / Ha

[0259] Table B2: Post-emergence testing

[0260]

[0261] *Data at 250g / Ha.

Claims

1. A compound having formula (I) or a salt or N-oxide thereof: in R 1 is C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxyC1-C6 alkyl, or C3-C6 cycloalkyl; R 2 is phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms independently selected from N, O and S, and wherein each phenyl and heteroaryl moiety may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and are represented by R 7 The group represented by is substituted; R 4 is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1, 2 or 3 nitrogen atoms, and wherein the heteroaryl moiety is attached to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl moiety can each be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 9 The group represented by is substituted; R 5 is hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl; 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 alkylsulfonylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, or N,N-di(C1-C4 alkyl)aminocarbonyl; R 9 is formyl, cyano, nitro, hydroxyl, 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 alkylsulfonylamino, 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; Any two adjacent R 9 The groups together with the carbon atoms 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 replaced by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 10 or Any two adjacent R 9 The groups together with the carbon atoms 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 independently selected from N, O and S, and wherein the heteroaryl moiety may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 10 or Any two adjacent R 9 The 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 a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and which are represented by R 10 The group represented by is substituted; R 10 It is halogen, C1-C3 alkyl, or C1-C3 alkoxy.

2. The compound according to claim 1, wherein R 2 is phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein each phenyl and heteroaryl moiety may be optionally substituted by 1, 2 or 3 residues which may be the same or different and are represented by R 7 The group represented is substituted.

3. The compound according to claim 1 or claim 2, wherein R 2 is optionally replaced by 1 or 2 which may be the same or different from R 7 The group represents a phenyl group substituted with.

4. The compound according to any one of claims 1 to 3, wherein R 5 It is hydrogen or C1-C3 alkyl.

5. The compound according to any one of claims 1 to 4, wherein R 7 It 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.

6. The compound according to any one of claims 1 to 5, wherein R 4 is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1, 2 or 3 nitrogen atoms, and wherein the heteroaryl moiety is attached to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl moiety can each be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are represented by R 9 The group represented is substituted.

7. The compound according to any one of claims 1 to 6, wherein R 4 is a heteroaryl group, wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 2 or 3 nitrogen atoms, and wherein the heteroaryl moiety is attached to the remainder of the molecule via a nitrogen atom in the heteroaryl ring, and wherein the heteroaryl moiety can each be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are represented by R 9 The group represented is substituted.

8. The compound according to any one of claims 1 to 7, wherein R 9 is formyl, cyano, nitro, hydroxyl, 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 alkylsulfonylamino, 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 The groups together with the carbon atoms 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 replaced by 1, 2 or 3 residues which may be the same or different and which are represented by R 10 or Any two adjacent R 9 The groups together with the carbon atoms 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 independently selected from N, O and S, and wherein the heteroaryl moiety may be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are represented by R 10 or Any two adjacent R 9 The 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 a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted by 1, 2 or 3 residues which may be the same or different and which are represented by R 10 The group represented is substituted.

9. The compound according to any one of claims 1 to 7, wherein R 9 is formyl, cyano, nitro, halogen, C1-C4 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C2 haloalkoxy, C2-C3 alkenyloxy, cyano C1-C2 alkoxy, C1-C3 alkoxy C1-C3 alkyl, C1-C3 alkoxy C1-C3 alkoxy, C1-C3 alkoxycarbonyl C1-C3 alkoxy, C1-C3 alkoxycarbonyl, C1-C3 Alkylsulfanyl, C1-C3 alkylsulfonyl, C1-C3 alkylcarbonyl, C1-C3 alkylaminocarbonyl, C1-C3 alkylcarbonylamino, C1-C3 alkylamino, C1-C3 alkoxy C1-C3 alkylaminocarbonyl, C1-C2 alkoxy C1-C2 alkylcarbonylamino, C3-C4 alkenylcarbonylamino, C3-C4 cycloalkyl, or N,N-di(C1-C3 alkyl)amino; or Any two adjacent R 9 The groups together with the carbon atoms to which they are attached may form a C5-C6 cycloalkyl ring or a phenyl ring, wherein the C5-C6 cycloalkyl and phenyl portions may be optionally replaced by a single R 10 group substitution; or Any two adjacent R 9 The groups together with the carbon atom to which they are attached may form a 6-membered heteroaryl ring, wherein the heteroaryl moiety is a 6-membered aromatic ring containing a single nitrogen atom, and wherein the heteroaryl moiety may be optionally substituted by a single R 10 group substitution; or Any two adjacent R 9 The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heterocyclyl ring, wherein the heterocyclyl moiety is a 5- or 6-membered ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted with a single R 10 Group substitution.

10. The compound according to any one of claims 1 to 9, wherein R 10 It is halogen or C1-C3 alkoxy.

11. A herbicidal composition comprising a compound according to any one of the preceding claims and an agriculturally acceptable formulation adjuvant.

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

13. The herbicidal composition according to claim 12, wherein The additional pesticide is a herbicide or a herbicide safener.

14. A method of controlling the growth of unwanted plants, the method comprising applying a compound of formula (I) according to any one of claims 1 to 10 or a herbicidal composition according to any one of claims 11 to 13 to the unwanted plants or the locus thereof.

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

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