Herbicidal cinnoline derivatives

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1. 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 weeds in crops of useful plants. #imgabs0#

Description

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

[0002] EP 0 273 325, EP 0 274 717 and US Pat. No. 5,183,891 describe cinnoline derivatives as herbicides.

[0003] According to the present invention, there is provided a compound having formula (I):

[0004]

[0005] in

[0006] X is O, NR 13 or S;

[0007] R 1 is optionally replaced by 1, 2, 3 or 4 R 7 A phenyl group substituted with

[0008] R 2 is halogen, cyano, cyano C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C2-C6 alkenyl, C2-C6 alkenyloxy C1-C6 alkyl, -CR 11 =N-OR 10 , oxo-C1-C6 alkyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N, O and S), heterocyclyl, or heterocyclyloxy, where the heterocyclyl moiety is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N, O and S, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties can each be optionally substituted by 1, 2 or 3 R 8 and wherein the heteroaryl and heterocyclyl moieties may be attached to the remainder of the molecule through a carbon or nitrogen atom;

[0009] R 3is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenylC1-C3 alkyl, wherein the phenyl portion may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and are represented by R 12 The group represented by substituted;

[0010] R 4 、R 5 , and R 6 each independently selected from hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl;

[0011] R 7 is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, or C1-C6 alkylsulfonyl; or

[0012] Any two adjacent R 7 The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heterocyclyl ring containing 1 or 2 heteroatoms selected from O and N, or any two adjacent R 7 The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heteroaryl ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring or heteroaryl ring may be optionally substituted by 1, 2, 3 or 4 groups which may be the same or different and are composed of R 9 The group represented by substituted;

[0013] R 8 and R 9 Each independently selected from halogen, C1-C3 alkyl, C1-C3 haloalkyl, and C1-C3 alkoxy;

[0014] R 10 and R 11 are each independently selected from hydrogen and C1-C3 alkyl;

[0015] R 12 is halogen, cyano, C1-C3 alkyl, or C1-C3 alkoxy;

[0016] R 13 is hydrogen, C1-C3 alkyl, or C1-C3 alkoxy;

[0017] or a salt or N-oxide thereof.

[0018] Surprisingly, it has been found that the novel compounds of formula (I) possess a very advantageous level of herbicidal activity for practical purposes.

[0019] 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.

[0020] 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).

[0021] According to a fourth aspect of the present invention, there is provided use of a compound of formula (I) as a herbicide.

[0022] When substituents are indicated as being "optionally substituted", this means that they may or may not carry one or more substituents, which may be the same or different, such as one, two or three R 8 Substituents. For example, C1-C8 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.

[0023] As used herein, the term "cyano" refers to a -CN group.

[0024] As used herein, the term "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo), or iodine (iodo).

[0025] As used herein, the term "hydroxy" refers to an -OH group.

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

[0027] As used herein, the term "nitro" refers to a -NO2 group.

[0028] 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 from 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 alkyl include, but are not limited to, methyl, ethyl, n-propyl, and isomers thereof, such as isopropyl. A "C1-C6 alkylene" group 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 alkylene include, but are not limited to, -CH2-, -CH2CH2-, and -(CH2)3-.

[0029] As used herein, the term "C1-C6 haloalkyl" refers to a C1-C6 alkyl group as generally defined above, which is substituted with one or more halogen atoms, which may be the same or different. The terms "C1-C4 haloalkyl" and "C1-C3 haloalkyl" should be interpreted accordingly. Examples of C1-C6 haloalkyl include, but are not limited to, trifluoromethyl.

[0030] As used herein, the term "C1-C6 dihaloalkyl" refers to a C1-C6 alkyl group as generally defined above, which is substituted with two halogen atoms, which may be the same or different. The terms "C1-C4 dihaloalkyl" and "C1-C3 dihaloalkyl" should be interpreted accordingly. Examples of C1-C6 dihaloalkyl include, but are not limited to, difluoromethyl.

[0031] As used herein, the term "cyano C1-C6 alkyl" refers to a C1-C6 alkyl group as generally defined above, which is substituted with one or more cyano groups as defined above. Examples of cyano C1-C6 alkyl include, but are not limited to, 2-cyanomethyl and 2-cyanoethyl.

[0032] As used herein, the term "C1-C6 haloalkoxy" refers to a C1-C6 alkoxy group as generally defined above, which is substituted with one or more halogen atoms, which may be 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.

[0033] 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.

[0034] 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 from 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 groups include, but are not limited to, ethenyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), and but-1-enyl.

[0035] 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 from 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 groups include, but are not limited to, ethynyl, prop-1-ynyl, but-1-ynyl.

[0036] As used herein, the term "C1-C6 alkoxy C1-C6 alkyl" refers to a b OR a - group, wherein R b is a C1-C6 alkyl group as generally defined above, and R a is C1-C6 alkylene as generally defined above.

[0037] As used herein, the term "cyano C1-C6 alkyl" refers to a C1-C6 alkyl group as generally defined above, which is substituted with one or more cyano groups as defined above. 1- Examples of C6 alkyl groups include, but are not limited to, 2-cyanoethyl.

[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 cycloalkylC1-C6 alkyl" refers to a C3-C6 cycloalkyl ring attached to the rest of the molecule via a C1-C6 alkylene linker as defined above.

[0040] As used herein, the term "C1-C6 alkoxy C2-C6 alkenyl" refers to a group having the formula R b OR a - group, wherein R b is a C1-C6 alkyl group as generally defined above, and Ra is a C1-C6 alkenyl group as generally defined above. Examples of C1-C6 alkoxy C2-C6 alkenyl groups include, but are not limited to, 1-methoxyvinyl and 1-ethoxyvinyl.

[0041] As used herein, the term "C2-C6 alkenyloxy C1-C6 alkyl" refers to a b OR a - group, wherein R b is a C2-C6 alkenyl group as generally defined above, and R a is a C1-C6 alkylene group as generally defined above.

[0042] As used herein, the term "oxo-C1-C6 alkyl" refers to a group having the formula -R a CHO group, where R a is a C1-C6 alkenyl group as generally defined above. Examples of "oxo-C1-C6" alkyl groups include, but are not limited to, 2-oxoethyl.

[0043] As used herein, the term "phenoxy" refers to a phenyl ring attached to the rest of the molecule through an oxygen atom.

[0044] As used herein, the term "phenyl C1-C3 alkyl" refers to a phenyl ring attached to the rest of the molecule via a C1-C3 alkylene linker as defined above.

[0045] As used herein, the term "heterocyclyl" refers to a stable 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms, wherein these heteroatoms are individually selected from nitrogen, oxygen and sulfur. The heterocyclyl group can be bonded to the remainder of the molecule via a carbon atom or a heteroatom. Examples of heterocyclyl groups include but are not limited to azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolane, dithiolanyl and thiazolidinyl.

[0046] As used herein, the term "heterocyclyloxy" refers to a heterocyclyl ring attached to the rest of the molecule through an oxygen atom.

[0047] As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic group containing 1, 2, 3, or 4 heteroatoms independently selected from nitrogen, oxygen, and sulfur. Examples of heteroaryl groups include, but are not limited to, furyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, or pyridyl.

[0048] As used herein, the term "C1-C6 alkylcarbonyl" refers to a group having the formula -C(O)R aA group in which R a is a C1-C6 alkyl group as generally defined above.

[0049] As used herein, the term "C1-C6 alkylsulfanyl" refers to a group having the formula -SR a A group in which R a is C as defined above 1- C6 alkyl group. The terms "C1-C4 alkylsulfanyl" and "C1-C3 alkylsulfanyl" should be interpreted accordingly. 1-6 Examples of alkylsulfanyl groups include, but are not limited to, methylsulfanyl groups.

[0050] 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.

[0051] 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.

[0052] 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). As a result of restricted rotation around a single bond, atropisomers may also 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).

[0053] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form (such as N-oxides), or in 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.

[0054] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. For example, they are described in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton (1991).

[0055] The following list provides information on the substituents X, R, and 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 and R 13 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.

[0056] X is O, N, or S. In one group of embodiments, X is O. In another group of embodiments, X is S. In another group of embodiments, X is N.

[0057] R 1 is optionally replaced by 1, 2, 3 or 4 R 7 Preferably, R 1 is optionally replaced by 1, 2 or 3 R 7 More preferably, R 1 is optionally replaced by 1 or 2 R 7 More preferably, R 1 is optionally replaced by a single R 7 Even more preferably, R 1 Is in the position of a single R 7 The group represents a phenyl group substituted with .

[0058] In one set of embodiments, R 1is 4-(trifluoromethoxy)phenyl, 4-chlorophenyl, 3,4-dimethoxyphenyl, 4-methylsulfanylphenyl, 3-chloro-5-methyl-phenyl, 4-(trifluoromethyl)phenyl, 4-cyanophenyl, 7-quinolyl, 2,2-difluoro-1,3-benzodioxol-5-yl, 1-methylindazol-6-yl, 2,2,3,3-tetrafluoro-1,4-benzodioxin-6-yl, 3-chloro-4-methyl-phenyl, 3,4-dichlorophenyl, 3-cyanophenyl, 3-chlorophenyl, or 3-chloro-4-fluoro-phenyl.

[0059] In another set of embodiments, R 1 is 4-(trifluoromethoxy)phenyl, 4-chlorophenyl, or 3,4-dimethoxyphenyl. In another embodiment, R 1 It is 4-(trifluoromethoxy)phenyl or 4-chlorophenyl.

[0060] R 2 is halogen, cyano, cyano C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkylcarbonyl, C2-C6 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy C2-C4 alkenyl, C2-C4 alkenyloxy C1-C3 alkyl, -CR 11 =N-OR 10 , oxo-C1-C4 alkyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N and O), heterocyclyl, or heterocyclyloxy, where the heterocyclyl moiety is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties may each be optionally substituted by 1, 2 or 3 R 8 The group represented is substituted.

[0061] Preferably, R 2 is halogen, cyano, cyano C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkylcarbonyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C3 alkoxy C2-C3 alkenyl, C2-C3 alkenyloxy C1-C3 alkyl, -CR 11 =N-OR 10 , oxo-C1-C3 alkyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N and O), heterocyclyl, heterocyclyloxy, where the heterocyclyl moiety is a 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties can each be optionally substituted by 1, 2 or 3 R 8The group represented is substituted.

[0062] More preferably, R 2 is halogen, cyano, cyano C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkylcarbonyl, C2-C4 alkenyl, C1-C3 alkoxy C2-C3 alkenyl, -CR 11 =N-OR 10 , oxo-C1-C3 alkyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N and O), heterocyclyl, heterocyclyloxy, where the heterocyclyl moiety is a 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties can each be optionally substituted by 1, 2 or 3 R 8 The group represented is substituted.

[0063] Even more preferably, R 2 is halogen (preferably bromine), cyano, cyanomethyl, difluoromethyl, acetyl, vinyl, 1-methoxyvinyl, 1-ethoxyvinyl, -CR 11 =N-OR 10 , 2-oxo-ethyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N and O), heterocyclyl, heterocyclyloxy, where the heterocyclyl moiety is a 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties may each be optionally substituted by 1, 2 or 3 heteroatoms independently selected from N and O, which may be the same or different and are represented by R 8 The group represented is substituted.

[0064] Still more preferably, R 2 is cyano, cyanomethyl, difluoromethyl, acetyl, vinyl, 1-methoxyvinyl, 1-ethoxyvinyl, N-methoxy-C-methylcarbonimido, N-hydroxy-C-methyl-carbonimido, 2-oxo-ethyl, nitro, phenyl, phenoxy, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, pyrrolidinyl, piperidinyl, morpholinyl, and wherein the phenyl, phenoxy, oxazolyl, isoxazolyl, pyrazolyl, and triazolyl moieties may each be optionally replaced by a single R 8 The substituent represented is substituted.

[0065] In a further preferred embodiment, R 2is cyano, cyanomethyl, difluoromethyl, acetyl, vinyl, 1-methoxyvinyl, 1-ethoxyvinyl, N-methoxy-C-methylcarbonimido, N-hydroxy-C-methyl-carbonimido, 2-oxo-ethyl, nitro, phenoxy, 5-oxazol-2-yl, isoxazol-3-yl, pyrazol-1-yl, triazol-1-yl, triazol-2-yl, 1-piperidinyl, morpholinyl, and wherein the phenoxy, isoxazolyl, pyrazolyl, and triazolyl moieties can each be optionally replaced by a single R 8 The substituent represented is substituted.

[0066] In another preferred embodiment, R 2 is cyano, cyanomethyl, difluoromethyl, acetyl, vinyl, 1-methoxyvinyl, 1-ethoxyvinyl, N-methoxy-C-methylcarbonimido, N-hydroxy-C-methyl-carbonimido, 2-oxo-ethyl, nitro, phenoxy, 5-oxazol-2-yl, 5-(difluoromethyl)isoxazol-3-yl, 4-chloropyrazol-1-yl, 4-(trifluoromethyl)triazol-1-yl, 4-(trifluoromethyl)triazol-2-yl, 1-piperidinyl, or morpholinyl.

[0067] R 2 is cyano, C1-C6 alkylcarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C2-C6 alkenyl, C2-C6 alkenyloxy C1-C6 alkyl, -CR 11 =N-OR 10 , phenyl, phenoxy, heteroaryl (wherein the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N, O and S), heterocyclyl, or heterocyclyloxy, where the heterocyclyl portion is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N, O and S, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy portions can each be optionally substituted by 1, 2 or 3 R 8 The group represented is substituted.

[0068] Preferably, R 2 is cyano, C1-C6 alkylcarbonyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy C2-C6 alkenyl, C3-C6 alkenyloxy C1-C4 alkyl, -CR 11 =N-OR 10, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N, O and S), heterocyclyl, heterocyclyloxy, and wherein the heterocyclyl moiety is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N, O and S, wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties may each be optionally substituted by 1, 2 or 3 R groups which may be the same or different 8 The group represented is substituted.

[0069] More preferably, R 2 is cyano, C1-C4 alkylcarbonyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C4 alkoxy C2-C4 alkenyl, C3-C4 alkenyloxy C1-C3 alkyl, -CR 11 =N-OR 10 , phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O), heterocyclyl, heterocyclyloxy, where the heterocyclyl moiety is a 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N, O and S, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties may each be optionally substituted by 1 or 2 R 8 The group represented is substituted.

[0070] Still more preferably, R 2 is cyano, C1-C3 alkylcarbonyl, C1-C3 alkoxy C2-C3 alkenyl, -CR 11 =N-OR 10 , phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O), or heterocyclyl, where the heterocyclyl moiety is a 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl moiety can each be optionally substituted by 1 or 2 R 8 The group represented is substituted.

[0071] Even more preferably, R 2 is cyano, acetyl, propionyl, 2-methylpropionyl, 1-methoxyvinyl, 1-ethoxyvinyl, N-methoxy-C-methylcarbamidyl, N-ethoxy-C-methylcarbamidyl, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O), or heterocyclyl, where the heterocyclyl moiety is a 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy moiety can each be optionally substituted by a single R8 The group represented is substituted.

[0072] Even more preferably, R 2 It is cyano, acetyl, 1-methoxyvinyl, 1-ethoxyvinyl, N-methoxy-C-methylcarbonimido, 4-fluorophenyl, 4-fluorophenoxy, or oxazol-2-yl.

[0073] In another preferred embodiment, R 2 is cyano C1-C4 alkyl, C1-C4 dihaloalkyl, C2-C6 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy C2-C4 alkenyl, C2-C4 alkenyloxy C1-C3 alkyl, -CR 11 =N-OR 10 , oxo-C1-C4 alkyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N and O), heterocyclyl, or heterocyclyloxy, where the heterocyclyl moiety is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties may each be optionally substituted by 1, 2 or 3 R 8 The group represented is substituted.

[0074] In another preferred embodiment, R 2 is cyano C1-C3 alkyl, C1-C3 dihaloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy C2-C4 alkenyl, C2-C3 alkenyloxy C1-C3 alkyl, -CR 11 =N-OR 10 , oxo-C1-C3 alkyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N and O), heterocyclyl, or heterocyclyloxy, where the heterocyclyl moiety is a 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties may each be optionally substituted by 1, 2 or 3 R 8 The group represented is substituted.

[0075] In yet another preferred set of embodiments, R 2is cyanomethyl, difluoromethyl, vinyl, 1-methoxyvinyl, 1-ethoxyvinyl, N-methoxy-C-methylcarbonimido, N-hydroxy-C-methyl-carbonimido, 2-oxo-ethyl, phenoxy, 5-oxazol-2-yl, 5-(difluoromethyl)isoxazol-3-yl, 4-chloropyrazol-1-yl, 4-(trifluoromethyl)triazol-1-yl, 4-(trifluoromethyl)triazol-2-yl, 1-piperidinyl, or morpholinyl.

[0076] R 3 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenylC1-C3 alkyl, wherein the phenyl portion may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and are represented by R 12 Preferably, R 3 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C1-C4 alkoxyC1-C3 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, or phenylC1-C2 alkyl, wherein the phenyl portion may be optionally substituted by 1, 2, 3 or 4 residues which may be the same or different and are represented by R 12 More preferably, R 3 is hydrogen, C1-C6 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C1-C4 alkoxyC1-C3 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, phenyl, or benzyl, wherein the phenyl moiety may be optionally substituted by 1, 2, or 3 residues which may be the same or different and are represented by R 12 More preferably, R 3 is hydrogen, C1-C6 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C1-C4 alkoxyC1-C3 alkyl, phenyl, or benzyl, wherein the phenyl moiety may be optionally replaced by 1 or 2 residues which may be the same or different and are represented by R 12 In one embodiment, R 3 is hydrogen or C1-C6 alkyl. Preferably, R 3 is hydrogen or C1-C4 alkyl, more preferably hydrogen or C1-C3 alkyl. Even more preferably, R 3 is hydrogen, methyl, or ethyl. Still more preferably, R 3 is hydrogen or methyl.

[0077] R 4 and R 5are each independently selected from hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl, and R 6 It's hydrogen.

[0078] Preferably, R 4 and R 5 are each independently selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, and C1-C4 alkylsulfonyl, and R 6 It's hydrogen.

[0079] More preferably, R 4 and R 5 are each independently selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, and C1-C3 alkylsulfonyl, and R 6 It's hydrogen.

[0080] Still more preferably, R 4 and R 5 are each independently selected from hydrogen, fluorine, bromine, cyano, C1-C4 alkyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylsulfanyl, and methylsulfonyl, and R 6 It's hydrogen.

[0081] Even more preferably, R 4 and R 5 are each independently selected from hydrogen, fluorine, bromine, cyano, methyl, isobutyl, methoxy, and trifluoromethyl, and R 6 It's hydrogen.

[0082] In one embodiment, R 4 、R 5 and R 6 are each independently selected from hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl. Preferably, R 4 、R 5 and R 6 are each independently selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, and C1-C4 alkylsulfonyl. More preferably, R4 、R 5 and R 6 are each independently selected from hydrogen, halogen, cyano, C1-C4 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, and C1-C3 alkylsulfonyl. Still more preferably, R 4 、R 5 and R 6 are each independently selected from hydrogen, fluorine, bromine, cyano, C1-C4 alkyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylsulfanyl, and methylsulfonyl. Even more preferably, R 4 、R 5 and R 6 Each is independently selected from hydrogen, fluorine, bromine, cyano, methyl, isobutyl, methoxy, and trifluoromethyl.

[0083] In one set of embodiments, R 4 and R 5 are each independently selected from hydrogen, fluorine, bromine, cyano, methyl, isobutyl, methoxy, and trifluoromethyl, and R 6 In another embodiment, R 4 、R 5 and R 6 It's all hydrogen.

[0084] R 7 is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, or C1-C6 alkylsulfonyl; or

[0085] Any two adjacent R 7 The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heterocyclyl ring containing 1 or 2 heteroatoms selected from O and N, or any two adjacent R 7 The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heteroaryl ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring or heteroaryl ring may be optionally substituted by 1, 2, 3 or 4 groups which may be the same or different and are composed of R 9 The group represented by substituted;

[0086] Preferably, R 7 is halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkylsulfanyl, or C1-C3 alkylsulfonyl; or

[0087] Any two adjacent R 7The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heterocyclyl ring containing 1 or 2 heteroatoms selected from O and N, or any two adjacent R 7 The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heteroaryl ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring or heteroaryl ring may be optionally substituted by 1, 2, 3 or 4 groups which may be the same or different and are composed of R 9 The group represented by substituted;

[0088] More preferably, R 7 is halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, or C1-C3 alkylsulfanyl; or

[0089] Any two adjacent R 7 The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heterocyclyl ring containing 1 or 2 oxygen atoms, or any two adjacent R 7 The groups together with the carbon atom to which they are attached may form a 5-membered or 6-membered heteroaryl ring containing 1 or 2 nitrogen atoms, and wherein the heterocyclyl ring or heteroaryl ring may be optionally substituted by 1, 2, 3 or 4 groups which may be the same or different and are represented by R 9 The group represented is substituted.

[0090] Even more preferably, R 7 is chlorine, cyano, methyl, methoxy, trifluoroalkyl, trifluoromethoxy, methylsulfanyl, or any two adjacent R 7 The groups together with the carbon atom to which they are attached may form a quinolinyl, indazolyl, 1,3-benzoxadiazolyl, or 1,4-benzodioxinyl group, and wherein the quinolinyl, indazolyl, 1,3-benzoxadiazolyl, or 1,4-benzodioxinyl group may be optionally replaced by 1, 2, 3, or 4 groups which may be the same or different and are represented by R 9 The group represented is substituted.

[0091] In one set of embodiments, R 7 is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkylsulfanyl, and C1-C6 alkylsulfonyl; or

[0092] Any two adjacent R 7 The groups together with the carbon atoms to which they are attached may form a 5- or 6-membered heterocyclyl 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 groups which may be the same or different and which are represented by R 9 The group represented is substituted.

[0093] Preferably, R 7 is halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, or C1-C3 alkylsulfonyl; or

[0094] Any two adjacent R 7 The groups together with the carbon atom to which they are attached may form a 5- or 6-membered heterocyclyl 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 groups which may be the same or different and which are represented by R 9 The group represented is substituted.

[0095] More preferably, R 7 is halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkylsulfanyl, C1-C3 alkylsulfinyl, or C1-C3 alkylsulfonyl.

[0096] Even more preferably, R 7 is fluoro, bromo, chloro, cyano, methyl, ethyl, isopropyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylsulfanyl, methylsulfinyl, or methylsulfonyl; or

[0097] Any two adjacent R 7 The groups together with the carbon atom to which they are attached may form a 5- or 6-membered heterocyclyl ring containing 1 or 2 heteroatoms selected from O and N, and wherein the heterocyclyl ring may be optionally substituted by 1 or 2 groups which may be the same or different and which are represented by R 9 Even more preferably, R 7 is fluorine, bromine, chlorine, cyano, methyl, methoxy, trifluoromethyl, or trifluoromethoxy. Still more preferably, R 7 is chloro, methoxy, or trifluoromethoxy. Even more preferably, R 7 is chloro or trifluoromethoxy.

[0098] In another set of embodiments, R 7 is a C1-C6 haloalkoxy group. 7 is C1-C4 haloalkoxy; more preferably, R 7 is C1-C3 haloalkoxy; even more preferably, R 7 is a C1-C3 fluoroalkoxy group; and still more preferably, R 7 It is trifluoromethoxy.

[0099] R 8 and R 9Each is independently selected from halogen, C1-C3 alkyl, C1-C3 haloalkyl, and C1-C3 alkoxy.

[0100] Preferably, each R 8 is independently selected from halogen and C1-C3 haloalkyl. More preferably, each R 8 is independently selected from halogen and C1-C3 fluoroalkyl. Even more preferably, each R 8 Independently selected from fluoro, chloro, difluoromethyl and trifluoromethyl.

[0101] Preferably, each R 9 is independently selected from halogen and C1-C3 alkyl. More preferably, each R 9 is independently selected from halogen and methyl. Even more preferably, each R 9 Independently selected from fluoro and methyl.

[0102] In one set of embodiments, R 8 and R 9 are each independently selected from halogen, C1-C3 alkyl and C1-C3 alkoxy. 8 and R 9 Each is independently selected from halogen, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, or isopropoxy. More preferably, R 8 and R 9 are each independently selected from halogen, methyl, or methoxy. Still more preferably, R 8 and R 9 Each is independently selected from fluorine, chlorine, methyl, or methoxy. In one embodiment, R 8 It's fluorine.

[0103] R 10 and R 11 are each independently selected from hydrogen and C1-C3 alkyl. More preferably, R 10 and R 11 Each is independently selected from hydrogen, methyl and ethyl. In one embodiment, R 10 and R 11 They are all methyl.

[0104] R 12 is halogen, cyano, C1-C3 alkyl, or C1-C3 alkoxy. 12 is bromine, chlorine, fluorine, cyano, methyl or methoxy.

[0105] R 13 is hydrogen, C1-C3 alkyl, or C1-C3 alkoxy. 13 is hydrogen, methyl or methoxy. More preferably, R 13 It's hydrogen.

[0106] Among the compounds of formula (I) according to the present invention, preferably:

[0107] X is O, N, or S;

[0108] R 1 is optionally replaced by 1 or 2 R 7 A phenyl group substituted with

[0109] R 2 is cyano, acetyl, propionyl, 2-methylpropionyl, 1-methoxyvinyl, 1-ethoxyvinyl, N-methoxy-C-methylcarbamidyl, N-ethoxy-C-methylcarbamidyl, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O), or heterocyclyl, where the heterocyclyl moiety is a 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy moiety can each be optionally substituted by a single R 8 The group represented by substituted;

[0110] R 3 is hydrogen or C1-C3 alkyl;

[0111] R 4 、R 5 and R 6 It's all hydrogen;

[0112] R 7 is halogen or C1-C3 haloalkoxy; and

[0113] R 8 It's a halogen.

[0114] In another group of embodiments, X is O;

[0115] R 1 is optionally replaced by a single R 7 A phenyl group substituted with

[0116] R 2 is cyano, C1-C6 alkylcarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C2-C6 alkenyl, C2-C6 alkenyloxy C1-C6 alkyl, -CR 11 =N-OR 10, phenyl, phenoxy, heteroaryl (wherein the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N, O and S), heterocyclyl, or heterocyclyloxy, where the heterocyclyl portion is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N, O and S, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy portions can each be optionally substituted by 1, 2 or 3 R 8 The group represented by substituted;

[0117] R 3 is hydrogen, methyl or ethyl;

[0118] R 4 、R 5 and R 6 It's all hydrogen;

[0119] R 7 is halogen or C1-C3 haloalkoxy; and

[0120] R 8 It's a halogen.

[0121] In another group of embodiments, X is O;

[0122] R 1 is optionally replaced by a single R 7 A phenyl group substituted with

[0123] R 2 is cyano, acetyl, 1-methoxyvinyl, 1-ethoxyvinyl, N-methoxy-C-methylcarbonimido, 4-fluorophenyl, 4-fluorophenoxy, or oxazol-2-yl;

[0124] R 3 is hydrogen, methyl or ethyl;

[0125] R 4 、R 5 and R 6 are all hydrogen; and

[0126] R 7 is halogen or C1-C3 haloalkoxy.

[0127] In another group of embodiments, X is O;

[0128] R 1 is optionally replaced by a single R 7 A phenyl group substituted with

[0129] R 2is halogen, cyano, cyano C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkylcarbonyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C2-C6 alkenyl, C2-C6 alkenyloxy C1-C6 alkyl, -CR 11 =N-OR 10 , oxo-C1-C6 alkyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N, O and S), heterocyclyl, or heterocyclyloxy, where the heterocyclyl moiety is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N, O and S, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties can each be optionally substituted by 1, 2 or 3 R 8 and wherein the heteroaryl and heterocyclyl moieties may be attached to the remainder of the molecule through a carbon or nitrogen atom;

[0130] R 3 is hydrogen, methyl or ethyl;

[0131] R 4 、R 5 and R 6 It's all hydrogen;

[0132] R 7 is a C1-C3 haloalkoxy group;

[0133] R 8 are fluorine, chlorine, difluoromethyl and trifluoromethyl.

[0134] R 10 is hydrogen or methyl; and

[0135] R 11 It's methyl.

[0136] In yet another group of embodiments, X is O;

[0137] R 1 is optionally replaced by a single R 7 A phenyl group substituted with

[0138] R 2 is cyano C1-C4 alkyl, C1-C4 dihaloalkyl, C2-C6 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy C2-C4 alkenyl, C2-C4 alkenyloxy C1-C3 alkyl, -CR 11 =N-OR 10, oxo-C1-C4 alkyl, nitro, phenyl, phenoxy, heteroaryl (wherein the heteroaryl moiety is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms independently selected from N and O), heterocyclyl, or heterocyclyloxy, where the heterocyclyl moiety is a 4-membered, 5-membered or 6-membered non-aromatic monocyclic ring containing 1 or 2 heteroatoms independently selected from N and O, and wherein the phenyl, phenoxy, heteroaryl, heterocyclyl and heterocyclyloxy moieties may each be optionally substituted by 1, 2 or 3 R 8 The group represented by substituted;

[0139] R 3 is hydrogen, methyl or ethyl;

[0140] R 4 、R 5 and R 6 It's all hydrogen;

[0141] R 7 is chloro, methoxy, or trifluoromethoxy;

[0142] R 8 are fluorine, chlorine, difluoromethyl and trifluoromethyl.

[0143] R 10 is hydrogen or methyl; and

[0144] R 11 It's methyl.

[0145] In particularly preferred embodiments, the compound of formula (I) is selected from:

[0146] 5-[(E)-N-methoxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P1), 5-[(E)-N-methoxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P2), 5-(1-ethoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P3), and 5-(1-methoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P4). 5-oxazol-2-yl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P5), 5-(4-fluorophenyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P6), 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P7), 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P8), 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester Ester (P9), 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P10), 1-(4-chlorophenyl)-5-(4-fluorophenoxy)-4-oxo-cinnoline-3-carboxylic acid (P11), 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P12), 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P13), 5-[( Ethyl E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P14), 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P15), ethyl 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylate (P16), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylate (P17), 4 5-(2-oxoethyl)-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P18), 5-(4-chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P19), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-2-yl]cinnoline-3-carboxylic acid (P20), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-1-yl]cinnoline-3-carboxylic acid (P21),4-Oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)pyrazol-1-yl]cinnoline-3-carboxylic acid (P22), 4-Oxo-5-pyrrolidin-1-yl-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P23), 4-Oxo-5-(1-piperidinyl)-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P24), 5-morpholino-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P25), 5-morpholino-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P26), 4-Oxo-5-(1-piperidinyl)- 1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P27), 4-oxo-5-pyrrolidin-1-yl-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P28), 5-(1-ethoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P29), 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P30), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)pyrazol-1-yl]cinnoline-3-carboxylic acid ethyl ester (P31), 5-(4-chloropyrazol-1-yl)-4- Ethyl 1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P32), ethyl 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-1-yl]cinnoline-3-carboxylate (P33), ethyl 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-2-yl]cinnoline-3-carboxylate (P34), ethyl 5-(cyanomethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P35), ethyl 5-(difluoromethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P36), ethyl 5-(difluoromethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P37), 4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P41), and 5-cyano-1-(3,4-dimethoxyphenyl)-4-oxo-cinnoline-3-carboxylic acid ethyl ester (P42).

[0147] In another particularly preferred embodiment, the compound of formula (I) is selected from:

[0148] 5-[(E)-N-methoxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P1), 5-[(E)-N-methoxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P2), 5-(1-ethoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P3), and 5-(1-methoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P4). 5-oxazol-2-yl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P5), 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P7), 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P8), 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P9), 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P10), 1 -(4-chlorophenyl)-5-(4-fluorophenoxy)-4-oxo-cinnoline-3-carboxylic acid (P11), 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P12), 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P13), 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester Ester (P14), 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P15), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid ethyl ester (P16), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid (P17), 4-oxo-5-(2-oxoethyl)-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P18), 5-(4- chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-2-yl]cinnoline-3-carboxylic acid (P19), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-2-yl]cinnoline-3-carboxylic acid (P20), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-1-yl]cinnoline-3-carboxylic acid (P21), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)pyrazol-1-yl]cinnoline-3-carboxylic acid (P22),4-Oxo-5-(1-piperidinyl)-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P24), 5-morpholino-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P26), 5-(1-ethoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P29), 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P28), )phenyl]cinnoline-3-carboxylic acid ethyl ester (P30), 5-(4-chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P32), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-1-yl]cinnoline-3-carboxylic acid ethyl ester (P33), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-1-yl]cinnoline-3-carboxylic acid ethyl ester (P34), triazol-2-yl] cinnoline-3-carboxylic acid ethyl ester (P34), 5-(cyanomethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P35), 5-(difluoromethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P36), 5-(difluoromethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P37), 5- Ethyl cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P38), ethyl 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P39), 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P40), and 5-cyano-1-(3,4-dimethoxyphenyl)-4-oxo-cinnoline-3-carboxylic acid (P41).

[0149] In a further particularly preferred embodiment, the compound of formula (I) is selected from:

[0150] 5-[(E)-N-methoxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P1), 5-[(E)-N-methoxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P2), 5-(1-ethoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P3), and 5-(1-methoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P4). 5-oxazol-2-yl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P5), 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P7), 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P8), 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (P9), 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P10), 1-(4-chlorophenyl)-5-(4-fluorophenoxy)-4-oxo-cinnoline-3-carboxylic acid (P11), 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P14), 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P15), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline- 3-carboxylic acid ethyl ester (P16), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid (P17), 4-oxo-5-(2-oxoethyl)-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P18), 5-(4-chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P19), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-1-yl]cinnoline-3-carboxylic acid acid (P21), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)pyrazol-1-yl]cinnoline-3-carboxylic acid (P22), 4-oxo-5-(1-piperidinyl)-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P24), ethyl 5-(1-ethoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P29), ethyl 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (P30),5-(4-chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P32), 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-[4-(trifluoromethyl)triazol-1-yl]cinnoline-3-carboxylic acid ethyl ester (P33), 5-(cyanomethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P35), 5-(difluoromethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P36), cinnoline-3-carboxylic acid ethyl ester (P36), 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P38), 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (P39), 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (P40), and 5-cyano-1-(3,4-dimethoxyphenyl)-4-oxo-cinnoline-3-carboxylic acid (P41).

[0151] The compounds of the present invention can be prepared as shown in the following schemes, wherein, unless otherwise indicated, each variable is defined as above for compounds of formula (I). The following describes a general method for producing compounds of formula (I). Unless otherwise indicated herein, X, R 1 、R 2 、R 3 、R 4 、R 5 and R 6 is 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. 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.

[0152] Option 1:

[0153]

[0154] Compounds of formula (I) wherein X is oxygen and R 3 is hydrogen) can be obtained by hydrolysis of a compound of formula (I) (wherein X is oxygen and R is hydrogen) 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) in a suitable solvent (such as methanol, ethanol, dichloromethane, chloroform, ethyl acetate or tetrahydrofuran) and optionally a co-solvent (such as water). 3 other than hydrogen but any other R as defined above 3 Compounds of formula (I) can additionally be prepared by the methods described below.

[0155] Option 2:

[0156]

[0157] Compounds of formula (I) can be prepared from compounds of formula (B) wherein Y is F, Cl, Br or I. In an embodiment of the present invention, when R 2 When Y is phenoxy or heterocyclyloxy and F, the compound of formula (I) can be prepared by reacting with an appropriately substituted phenol or heterocyclyl alcohol in a S-phase similar to the conditions in the literature. N Ar reaction is prepared. Typically, the reaction is carried out in the presence of a base (such as potassium carbonate) in an organic solvent (such as dimethylacetamide or N,N-dimethylformamide) at an elevated temperature (such as 100°C to 170°C). This is shown in Scheme 2 above. The compound of formula (B) can be prepared by the following method.

[0158] Option 3:

[0159]

[0160] Compounds of formula (I) can additionally be prepared from compounds of formula (B) wherein Y is Cl, Br or I. In an embodiment of the present invention, when R 2 When it is C2-C6 alkenyloxy and Y is Br, the compound of formula (I) can be prepared by reacting with a stannane reagent in a Stirler reaction in the presence of a palladium catalyst (such as bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium) or (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride dichloromethane adduct) with or without a base (such as triethylamine) in a suitable organic solvent (such as toluene, 1,4-dioxane or N,N-dimethylformamide) at elevated reaction temperature (e.g., 120°C). This is shown in Scheme 3 above.

[0161] Option 4:

[0162]

[0163] In subsequent transformations, compounds of formula (I) wherein R 2 is a C1-C6 alkylcarbonyl) can be converted from a compound having formula (I) (wherein R 2 is a C2-C6 alkenyloxy group). Typically, the reaction is carried out by treating with an aqueous acid solution (such as hydrochloric acid) at a suitable temperature (20°C to 60°C), optionally in a suitable organic solvent (such as acetone, 1,4-dioxane or tetrahydrofuran). This is shown in Scheme 4 above.

[0164] Option 5:

[0165]

[0166] In a further transformation, a compound of formula (I) wherein R 2 Yes-CR 11 =N-OR 10 ) can be prepared from a compound of formula (I) (wherein R 2 is a C1-C6 alkylcarbonyl). Typically, the reaction is with a compound having the formula H2NOR 10 The compound (as free base or hydrochloride) is reacted with or without the addition of a base (such as sodium acetate, pyridine or potassium hydroxide aqueous solution) in a suitable organic solvent (such as ethanol, dimethyl sulfoxide, tetrahydrofuran, dimethyl ether or methanol) with or without additional water at elevated temperature. This is shown in Scheme 5 above.

[0167] Option 6:

[0168]

[0169] In an alternative transformation, compounds of formula (B) wherein Y is Br can be converted to compounds of formula (I) wherein R is Br by reaction under Stiller conditions with, for example, a heterocyclic stannane in the presence of a catalyst such as Pd-PEPPSI IPent and a base such as cesium fluoride in a suitable solvent such as 1,4-dioxane at elevated temperature such as 150°C. 2 is a C-attached heterocycle (such as oxazol-2-yl). This is shown in Scheme 6 above.

[0170] Option 7:

[0171]

[0172] In another transformation, compounds of formula (B) wherein Y is Br can be converted to compounds of formula (I) wherein R 2 is alkyl or phenyl). Typically, the reaction is carried out by reacting a compound of formula (B) with R 2-boronic acid or boroxane in the presence of a suitable catalyst (such as bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium), tris(dibenzylideneacetone)dipalladium or (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) dichloromethane adduct) or palladium diacetate optionally with a ligand (such as 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl), in the presence of a base (such as potassium carbonate or cesium carbonate, or tripotassium phosphate), in a suitable organic solvent (such as 1,4-dioxane, toluene or tetrahydrofuran), optionally in the presence of water, at elevated temperature. This is shown in Scheme 7 above.

[0173] Option 8:

[0174]

[0175] In another transformation, compounds of formula (B) wherein Y is Br can be converted to compounds of formula (I) wherein R 2 is a nitrile). Typically, the reaction is carried out by reacting a compound of formula (B) with zinc cyanide in the presence of a suitable catalyst (such as bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium), tris(dibenzylideneacetone)dipalladium or (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride dichloromethane adduct) or optionally palladium diacetate with a ligand (such as 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl) in a suitable organic solvent (such as dimethylformamide) at elevated temperature. This is shown in Scheme 8 above.

[0176] Option 9:

[0177]

[0178] Compounds of formula (B) wherein Y is Br, X=O and LG is a suitable leaving group such as F, Cl or Br can be prepared from compounds of formula (C) by treatment with a base such as a metal hydride, for example sodium hydride, or potassium carbonate, in a suitable solvent such as 1,4-dioxane, tetrahydrofuran or N,N-dimethylformamide at elevated temperature such as 100° C. This is shown in Scheme 9 above.

[0179] Option 10:

[0180]

[0181] Compounds with formula (C) (wherein Y is Br and LG is a suitable leaving group (such as F, Cl or Br)) can be prepared by the reaction of β-ketoesters with formula (D) and arene diazonium salts. Arene diazonium salts can be prepared in situ by the following: in the presence of an acid (such as hydrochloric acid), in water, aniline diazotization with sodium nitrite with formula (E), followed by reaction with a compound with formula (D) in the presence of a suitable base (such as sodium acetate or potassium acetate or potassium carbonate), in a suitable solvent (such as water, methanol or ethanol), at a temperature between 0°C and 25°C. Compounds with formula (E) are commercially available or can be prepared by methods familiar to those skilled in the art. This is shown in Scheme 10 above.

[0182] Option 11:

[0183]

[0184] Dicarbonyl compounds of formula (D) (wherein Y is Br and LG is a suitable leaving group (such as F, Cl or Br)) can be prepared from methyl ketone compounds of formula (F) and diesters of formula (G) via Claisen condensation by treating the methyl ketone with a suitable base (such as potassium tert-butoxide or sodium hydride) in a suitable solvent (such as tetrahydrofuran, N,N-dimethylformamide, toluene or 1,4-dioxane) and then reacting the mixture with a carbonate (such as dimethyl carbonate or diethyl carbonate) at a temperature between 0°C and 110°C. Compounds of formula (F) and compounds of formula (G) are commercially available or can be prepared by methods familiar to those skilled in the art. This is shown in Scheme 11 above.

[0185] The present invention further provides a method for controlling weeds in a place, the method comprising applying a composition comprising a compound of formula (I) to the place in which the amount of weeds to be controlled. In addition, the present invention can further provide a method for selectively controlling weeds in a place including useful (crop) plants and weeds, wherein the method comprises applying a composition according to the present invention to the place in which the amount of weeds to be controlled. '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. Plants to be controlled are usually unwanted plants (weeds). 'Place' means the area where a plant is growing or will grow. Application can be applied to the place before and / or after emergence of crop plants. Some crop plants can inherently tolerate the herbicidal action of compounds with formula (I).

[0186] The rate of application of the compound of formula (I) can vary within wide limits and depends on the nature of the soil, the method of application (before or after 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 present invention is usually applied at a rate of from 10 g / ha to 2500 g / ha, in particular from 25 g / ha to 1000 g / ha, more particularly from 25 g / ha to 250 g / ha.

[0187] Application is usually made 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.

[0188] 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-synthetase) (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 corn varieties, which are Herculex and Commercially available under the trade name GLUTAMIDE.

[0189] 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.

[0190] Examples of such plants are: (corn variety expressing CryIA(b) toxin); YieldGard (corn variety expressing CryIIIB(b1) toxin); YieldGard (maize varieties expressing CryIA(b) and CryIIIB(b1) toxins); (corn variety expressing Cry9(c) toxin); Herculex (maize varieties 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), CBAdvantage (Bt11 corn borer (CB) trait), RW (corn rootworm trait) and

[0191] Plant crops or their seed material can be both herbicide-resistant and simultaneously resistant to insect feeding ("stacked" transgenic events). For example, a seed can have the ability to express an insecticidal Cry3 protein while being tolerant to glyphosate.

[0192] 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 (for example improved storage stability, higher nutritional value and improved flavor).

[0193] The compounds of formula (I) (or compositions comprising the same) 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 ) and Sorghum, and may also be dicotyledonous species such as Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola, and Xanthium.

[0194] The compound of formula (I) can be used in unmodified form or preferably used together with adjuvants conventionally employed 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.

[0195] The herbicidal compositions generally comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of a compound of formula I and from 1 to 99.9% by weight of formulation adjuvants, which preferably include from 0 to 25% by weight of surface-active substances.

[0196] 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 dispersants (OD), oil suspensions (OF), oil-soluble liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), parent 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).

[0197] 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 a mixture of such agents to improve water dispersibility / solubility. The mixture is then ground into a fine powder. Similar compositions can also be granulated to form water-soluble granules (SG).

[0198] 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).

[0199] Granules (GR) can be formed by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or by absorbing 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 earths 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, if necessary, drying from preformed blank 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, dextrin, sugars and vegetable oils). One or more other additives may also be included in the granules (for example, an emulsifier, wetting agent or dispersant).

[0200] 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 (e.g. to improve water dilution or to prevent crystallization in a spray tank).

[0201] 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 can spontaneously emulsify when added to water, producing an emulsion with sufficient stability to allow spray application via appropriate equipment.

[0202] 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 with low solubility in water.

[0203] Microemulsions (MEs) 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 either 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.

[0204] Suspension concentrates (SC) can include aqueous or non-aqueous suspensions of finely dispersed insoluble solid particles of a compound of formula (I). SC can 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 can be included in the composition, and a suspending agent can be included to reduce the rate of particle settling. Alternatively, dry grinding can be used to add the compound of formula (I) to the water containing the reagent described above to produce the desired final product.

[0205] Aerosol formulations comprise a compound of formula (I) and a suitable propellant (e.g., n-butane). The compound of formula (I) can 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.

[0206] Capsule suspensions (CS) can be prepared in a manner similar to that of EW formulations, but with an additional polymerization stage to obtain an aqueous dispersion of oil droplets, each of which is encapsulated by a polymer shell and containing a compound of formula (I) and optionally a carrier or diluent for the droplet. The polymer shell can be produced by an interfacial polycondensation reaction or by a coacervation procedure. These compositions can provide controlled release of the compound of formula (I) and can be used for seed treatment. The compound of formula (I) can also be formulated in a biodegradable polymer matrix to provide slow, controlled release of the compound.

[0207] The composition may contain 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 the treated surface; or absorption or flow of the 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 the compound of formula (I)).

[0208] The wetting agent, dispersant and emulsifier may be a cationic, anionic, amphoteric or nonionic SAA.

[0209] Suitable cationic-type SAAs include quaternary ammonium compounds (eg, cetyltrimethylammonium bromide), imidazolines, and amine salts.

[0210] Suitable anionic SAAs include alkali metal salts of fatty acids, salts of fatty 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 (primarily monoesters) or with phosphorus pentoxide (primarily diesters), such as the reaction of lauryl alcohol with tetraphosphoric acid; these products may additionally be ethoxylated), sulfosuccinamates, paraffin or olefin sulfonates, taurates, lignosulfonates, and phosphates / sulfates of tristyrylphenol.

[0211] Suitable amphoteric types of SAA include betaine, propionate and glycinate.

[0212] Suitable SAAs of the nonionic type 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 said 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.

[0213] Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

[0214] The compounds of the present invention can 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), clonifen-sodium, ametryn, amitriptyline, aminopyralid, cypermethrin, atrazine, flubutamide-M, quinclorac, benquitrione, bensulfuron-methyl (including bensulfuron-methyl), bentazone, bicyclpyrone, bialaphos, bispyribac-sodium, bixlozone, herbicide, bromoxynil, butachlor, flubutamide, chlorfenapyr (including chlorfenapyr-ethyl), chlorsulfuron (including chlorsulfuron-methyl), chlorsulfuron (including chlorsulfuron-ethyl), chlorotoluron, chlorsulfuron, cyproconazole, chlorpyrifos, chlorpyrifos-butyl, chlorpyrifos-sodium ... cyfos), 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), diclosulam, diflufenican, fluazifop-butyl, dimethachlor, dimethofuram-S, dioxopyritrione, diquat dibromide, diquat Fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl (including fluazifop-butyl-ethyl), fluazifop-butyl, fluazifop-butyl, fluazifop-butyl (including fluazifop-butyl-butyl), fluazifop-butyl, fluazifop-butyl, fluazifop-butyl (including fluazifop-butyl-sodium), flufenacet, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl (including fluazifop-butyl-sodium), flufenacet, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl (including fluazifop-methyl-sodium), fluazifop-butyl (including fluazifop-butyl-sodium), fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl (including fluazifop-methyl-sodium), fluazifop-butyl (including fluazifop-butyl ... fluroxypyr-meptyl)), fluazifop-butyl, foramsulfuron, glufosinate (including L-glufosinate and its ammonium salts), glyphosate (including its hydrazine, isopropyl ammonium and potassium salts), halauxifen (including halauxifen-methyl), fluazifop-methyl (including fluazifop-methyl), hexazinone, hydantocidin, imazamox (including R-imazamox), imazapyr, imazapyr, imazapyr, indazine fluazifop-butyl, iodosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron (including iofensulfuron-sodium), ioxynil, isoproturon, isoxathiapiprolin,Lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron-methyl), mesotrione, metamitron, metazachlor, methizolin, isopropyl metolachlor, sulfone sulfamethoxam, metribuzin, metsulfuron-methyl, propamide, nicosulfuron, norfadazole, oxadiazon, epoxysulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, benzylpyridinium, picloram, pinoxaden, pretilachlor, primisulfuron-methyl, prometryn, propanil, cypermethrin, propyrisulfuron, propyrisulfuron, promethazine, prosulfuron, bispyribac, Pyraflufen (including pyraflufen-ethyl), pyraflufen, pyridazone, cypermethrin, pyrimisulfan, pyroxasulfone, pyraflufen, quinclorac, quinclorac, quizalofop-P (including quizalofop-P-ethyl and quizalofop-P-tefuryl), rimisoxafen, sulfaflufen, pyrimisulfan, sethoxydim, simazine, metolachlor, sulfaflufen, sulfenthiocarb, thiosulfuron, tethiocarb, tefuroxime ... ncarbazone), thifensulfuron-methyl, tiafenacil, tolpyralate, benzylpyrazone, triafamone, triafamone, wild malt, ether bensulfuron-methyl, bensulfuron-methyl (including bensulfuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), trifludimoxazin, trifluralin, trifloxysulfuron, 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 ester, 4-hydroxy 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,4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (including agrochemically acceptable esters thereof, for example, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, prop-2-ynyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-ylcarboxylic acid cyanomethyl ester), 3-ethylsulfanyl-N-(1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, 3-(isopropylsulfanylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)- )-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, 3-(isopropylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, 3-(ethylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)- -yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, ethyl 2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridinyl]oxy]acetate and 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one.

[0215] The compound of the present invention or mixture can also be used in combination with one or more herbicide safeners. Examples of such safeners include fenoxacic acid, cloquintocet (including cloquintocet-mexyl), cyclopropylsulfonamide, dichloropropane, fenoxacic acid (including fenoxacic acid-ethyl), fenoxacic acid, fluazifop, fenoxacic acid, isoxadiazole (including isoxadiazole-ethyl), mefenpyr (including pyrazole oxalic acid-diethyl), herbicide safeners (metcamifen) and fenoxacic acid nitrile.

[0216] The mixing partners of the compound of formula (I) can also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, 16th edition, British Crop Protection Council, 2012. The mixing ratio of the compound of formula (I) to the mixing partner is preferably from 1:100 to 1000:1.

[0217] These mixtures can advantageously be used in the abovementioned formulations ("active ingredient" in this case relates to the corresponding mixture of the compound of formula (I) with the mixing partner).

[0218] The compound of the present invention or mixture can also be used in combination with one or more herbicide safeners. Examples of such safeners include fenoxacic acid, cloquintocet (including cloquintocet-mexyl), cyclopropylsulfonamide, dichloropropane, fenoxacic acid (including fenoxacic acid-ethyl), fenoxacic acid, fluazifop, fenoxacic acid, isoxadiazole (including isoxadiazole-ethyl), mefenpyr (including pyrazole oxalic acid-diethyl), herbicide safeners (metcamifen) and fenoxacic acid nitrile.

[0219] Particularly preferred are mixtures of compounds of formula (I) with cyprosulfamide, isoxadiazole, cloquintocet-mexyl and / or metcamifen.

[0220] The safeners of compounds of formula (I) may also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, 16th edition (BCPC), 2012. References to cloquintocet-mexyl also apply to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts (as disclosed in WO 02 / 34048).

[0221] 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.

[0222] 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 sequentially 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, together with insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with other carriers, surfactants or adjuvants commonly used in the formulation field to promote application.

[0223] 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.

[0224] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruit.

[0225] The term "plant propagation material" should be construed as representing the reproductive parts of a plant, such as seeds, which can be used for the breeding of plants, and nutritious materials, such as cuttings or tubers (for example potatoes). Examples include seed (strictly speaking), roots, fruits, tubers, corms, rhizomes, and plant parts. Examples also include germinating plants and young plants that will be transplanted after germination or after emergence. These young plants can be protected before transplanting by being processed wholly or in part by dipping. Preferably, "plant propagation material" should be construed as representing a seed.

[0226] The pesticides mentioned herein using their common names are known, for example, from “The Pesticide Manual”, 15th edition, British Crop Protection Council 2009.

[0227] Compounds with formula (I) can be used in unmodified form, or preferably, used 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, particles and also encapsulations, for example, in polymeric materials in a known manner. For the type of composition, according to the intended purpose and the environment at that time, application methods are selected, such as spraying, atomizing, dusting, broadcasting, smearing or watering. Compositions can also contain other adjuvants, such as stabilizers, defoamers, viscosity modifiers, adhesives or tackifiers, together with fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0228] Suitable carriers and adjuvants, for example, for agricultural use, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated mineral substances, solvents, dispersions, wetting agents, tackifiers, thickeners, adhesives, or fertilizers. Such carriers are for example described in WO 97 / 33890.

[0229] 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 sequentially with other compounds. For example, these other compounds can be fertilizers or micronutrient donors or other formulations that affect plant growth. They can also be selective herbicides or non-selective herbicides, together with insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these formulations, if desired together with other carriers, surfactants or adjuvants commonly used in the formulation field to promote application.

[0230] 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.

[0231] Typically, the formulation comprises from 0.01% to 90% active ingredient by weight, from 0 to 20% agriculturally acceptable surfactant and 10% to 99.99% solid or liquid formulation inert agent and one or more adjuvants, the activating agent being by at least a compound having formula (I) together with components (B) and (C), and optionally other activating agents (particularly microbicides or preservatives or the like). Concentrated forms of the composition typically contain between about 2% and 80% by weight, preferably between about 5% and 70% activating agent. The application form of the formulation can, for example, contain from 0.01% to 20% by weight, preferably from 0.01% to 5% activating agent by weight. However, commercial products will preferably be formulated as concentrates, and end users will typically use diluted formulations.

[0232] The following table shows examples of individual compounds of formula (I) according to the present invention:

[0233]

[0234] Table 1: Individual compounds of formula (I) according to the invention

[0235]

[0236]

[0237] Table A-1 provides 48 compounds A-1.001 to A.1.048 of formula (I), wherein X is oxygen, and R 1 、R 2 、R 3 、R 4 、R 5 , and R 6 is as defined in Table 1.

[0238] Preparation Examples

[0239]

[0240]

[0241] The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable grinder to provide a wettable powder which can be diluted with water to give a suspension of the desired concentration.

[0242]

[0243] 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.

[0244] Emulsifiable concentrates

[0245]

[0246] Emulsions of any desired dilution which can be used in plant protection can be obtained from these concentrates by dilution with water.

[0247]

[0248] 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.

[0249] Extruder granules

[0250]

[0251] 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.

[0252] Coated granules

[0253] Active ingredient [compound of formula (I)] 8%

[0254] Polyethylene glycol (molecular weight 200) 3%

[0255] Kaolin 89%

[0256] 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.

[0257] Suspension concentrates

[0258]

[0259] The finely ground active ingredient is intimately mixed with adjuvants to give a suspension concentrate from which suspension concentrates of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0260] Flowable concentrate for seed treatment

[0261]

[0262]

[0263] The finely ground active ingredient is intimately mixed with adjuvants to give a suspension concentrate from which suspension concentrates of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0264] Extended-release capsule suspension

[0265] 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 is added a mixture of 2.8 parts of 1,6-hexanediamine in 5.3 parts of water. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% 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 an apparatus suitable for this purpose.

[0266] Examples

[0267] The following non-limiting examples provide specific synthetic methods for representative compounds of the present invention (as mentioned in Table 2 below).

[0268] List of abbreviations

[0269] °C = degrees Celsius, CDCl3 = chloroform-d, d = doublet, DCM = dichloromethane, dppf = 1,1′-ferrocenediyl-bis(diphenylphosphine), m = multiplet, MHz = megahertz, Pd-PEPPSI IPent = [1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride, q = quartet, s = singlet

[0270] Example 1: 5-(N-methoxy-C-methyl-carbonimido)-4-oxo-1-[4-(trifluoromethoxy)phenyl]isothiazolinone Synthesis of 3-Phenylinecarboxylic acid (Compound P2)

[0271] Step 1: Synthesis of 3-(2-bromo-6-fluoro-phenyl)-3-oxo-propionic acid methyl ester

[0272]

[0273] To a stirred solution of 1-(2-bromo-6-fluoro-phenyl)ethanone (5.0 g, 23.0 mmol) and dimethyl carbonate (37.3 g, 406 mmol) in N, N-dimethylformamide (20 mL) under nitrogen and cooled to 0 ° C. Sodium hydride (2.8 g, 69.1 mmol, 60 mass %) was added in batches. The reaction was allowed to warm to room temperature and stirred for 24 hours. The reaction mixture was slowly poured onto ice and acidified to pH 3 with concentrated hydrochloric acid. The phases were separated and the aqueous phase was re-extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate and evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 0 to 30% ethyl acetate in cyclohexane as eluent to obtain the desired product (mixture of tautomers) (3.34 g, 12.1 mmol, 52%) as a colorless liquid. 1 H NMR (400 MHz, CDCl3) δ = 7.46-7.36 (m, 1H), 7.33-7.28 (m, 1H), 7.15-6.98 (m, 1H), 3.98-3.90 (m, 2H), 3.79-3.61 (m, 3H) (data for keto form only)

[0274] Step 2: Synthesis of methyl (2E)-3-(2-bromo-6-fluoro-phenyl)-3-oxo-2-[[4-(trifluoromethoxy)phenyl]hydrazono]propionate

[0275]

[0276] To the solution of 4-(trifluoromethoxy) aniline (2.12g, 12.0mmol) in hydrochloric acid (10.0mL, 60.1mmol, 6mol / L) at 0 DEG C, dropwise add the solution of sodium nitrite (0.921g, 13.2mmol) in water (2.4mL, 12.0mol).Reactant mixture is stirred at 0 DEG C for 30 minutes, then added in batches in the suspension of 3-(the bromo-6-of 2-)-3-oxo-ethyl propionate (3.34g, 12.0mmol) and potassium acetate (6.0g, 60.1mmol) in water (2.4mL), causes formation of yellow solid.Reactant mixture is stirred 45 minutes and then it is heated to room temperature.After 90 minutes, reactant mixture is filtered, and solid is collected by filtration, to obtain the desired product (3.5g, 7.6mmol, 64%) in yellow solid. 1HNMR(400MHz, CDCl3)δ=13.25-13.07(m,1H),7.45-7.39(m,1H),7.33-7.28(m,1H),7.18-7.07(m,3H),7.02-6.92(m,2H),4.08-3.97(m,3H)

[0277] Step 3: Synthesis of methyl 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate

[0278]

[0279] To a solution of (2Z)-3-(2-bromo-6-fluoro-phenyl)-3-oxo-2-[[4-(trifluoromethoxy)phenyl]hydrazono]propionic acid methyl ester (3.53 g, 7.6 mmol) in dimethylformamide (30 mL) was added potassium carbonate (0.85 g, 8.38 mmol). The reaction mixture was heated at 100° C. for 1.5 hours. The cooled reaction mixture was poured onto ice, at which point a light-colored solid precipitated from the solution. The solid was collected by filtration to give the desired product as an off-white powder (3.3 g, 7.5 mmol, 98%). 1 H NMR (400MHz, CDCl3)δ=7.61-7.53(m,3H),7.46-7.41(m,2H),7.16-7.05(m,1H),6.97-6.87(m,1H),4.01-3.94(m,3H)

[0280] Step 4: Synthesis of methyl 5-(1-ethoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P3)

[0281]

[0282] To bis(triphenylphosphine)palladium dichloride (II) (0.048 g, 0.068 mmol) was added a solution of 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-methyl carboxylate (0.60 g, 1.35 mmol) in toluene (20 mL). The reaction mixture was degassed under a stream of nitrogen for 5 minutes, followed by the addition of tributyl(1-ethoxyvinyl)stannane (1.47 g, 4.1 mmol). The reaction mixture was heated at 120 ° C for 60 minutes under microwave irradiation. The reaction mixture was evaporated to dryness under reduced pressure to obtain a brown gum, which was purified by flash chromatography on silica gel using a gradient of 5%-100% ethyl acetate in cyclohexane as an eluent to obtain the desired product (0.43 g, 0.99 mmol, 70%) as an off-white solid. 1HNMR(400MHz, CDCl3)δ=7.62-7.52(m,3H),7.48-7.35(m,3H),7.19-7.08(m,1H),4.44- 4.39(m,1H),4.28-4.25(m,1H),4.12-4.03(m,2H),3.98-3.88(m,3H),1.41-1.31(m,3H)

[0283] Step 5: Synthesis of methyl 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P9)

[0284]

[0285] To ethyl 5-(1-ethoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (0.416 g, 0.96 mmol) in acetone (5.5 mL) was added aqueous hydrochloric acid (2 M, 5.5 mL, 11 mmol). The reaction mixture was heated at 60° C. for 3.5 hours. The reaction mixture was evaporated under reduced pressure to remove acetone, and the solid was collected by filtration to give the desired product (0.36 g, 0.87 mmol, 94%) as an off-white powder. 1 H NMR (400MHz, CDCl3)δ=7.73-7.67(m,1H),7.59-7.51(m,2H),7.52-7.42(m,2H),7.29-7.20(m,2H),4.03-3.89(m,3H),2.65-2.52(m,3H)

[0286] Step 6: Synthesis of methyl 5-(N-methoxy-C-methyl-carbonimido)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P1)

[0287]

[0288] To 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-methyl formate (0.47g, 1.16mmol) in a mixture of methanol (5mL) and water (1.5mL), O-methylhydroxylamine hydrochloride (0.15g, 1.7mmol) and sodium acetate (0.14g, 1.74mmol) are added. The reaction mixture is heated under reflux for 4.5 hours, and then allowed to stand at room temperature for 3 days. More O-methylhydroxylamine hydrochloride (0.15g, 1.74mmol) and sodium acetate (0.14g, 1.74mmol) are added and the reaction mixture is heated for 5 hours. The cooled reaction mixture is diluted with 2M aqueous hydrochloric acid solution, and the precipitated solid is collected by filtration. The solid is purified by flash chromatography on silica gel using the gradient of 5%-100% ethyl acetate in cyclohexane as eluent, to obtain the desired product (0.17g, 0.39mmol, 34%) as a white solid. 1 H NMR(400MHz, CDCl3)δ=7.67-7.59(m,1H),7.58-7.51(m,2H),7.50-7.43(m,2H) ),7.37-7.30(m,1H),7.23-7.15(m,1H),3.99-3.94(m,6H),2.28-2.21(m,3H)

[0289] Step 7: Synthesis of 5-(N-methoxy-C-methyl-carbonimido)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Compound P2)

[0290]

[0291] To a solution of 5-(N-methoxy-C-methyl-carbonimido)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (0.038 g, 0.087 mmol) in methanol (1 mL) and water (0.5 mL) was added lithium hydroxide monohydrate (0.0073 g, 0.17 mmol). The resulting solution was heated to 65 ° C for 2 hours. Methanol was removed under reduced pressure, and the pH of the resulting aqueous reaction mixture was adjusted to pH 2 by adding concentrated hydrochloric acid. The precipitated solid was collected by filtration and washed with cyclohexane to give the desired product (0.036 g, 0.084 mmol, 97%) as a white powder. 1 H NMR (400MHz, CDCl3)δ=7.86-7.74(m,1H),7.63-7.55(m,2H),7.55-7.45(m,3H),7.44-7.35(m,1H),4.06-3.95(m,3H),2.32-2.17(m,3H)

[0292] Example 2: Synthesis of 5-oxazol-2-yl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Compound P5)

[0293]

[0294] A mixture of 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (0.20 g, 0.45 mmol), Pd-PEPPSI IPent catalyst (0.029 g, 0.0361 mmol), cesium fluoride (0.14 g, 0.90 mmol) and tributyl (oxazol-2-yl) stannane (0.19 g, 0.54 mmol) in 1,4-dioxane (4 mL) was heated at 150 ° C for 30 + 30 minutes under microwave irradiation. The reaction mixture was diluted with 2M hydrochloric acid and extracted with ethyl acetate. The combined organics were concentrated to dryness under reduced pressure. The crude residue was purified by mass-directed reverse phase HPLC and then triturated with diethyl ether to obtain the desired product (0.026 g, 0.063 mmol, 14%) as a light yellow powder. 1 H NMR (400MHz, CDCl3)δ=7.91-7.81(m,3H),7.65-7.59(m,2H),7.58-7.47(m,3H),7.40-7.35(m,1H)

[0295] Example 3: Synthesis of 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Compound P10)

[0296]

[0297] To a suspension of 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.052 g, 0.13 mmol) in methanol (1.5 mL) was added a solution of lithium hydroxide hydrate (0.026 g, 0.61 mmol) in water (0.15 mL). The reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was acidified by the addition of 2M aqueous hydrochloric acid, at which point a light-colored solid precipitated from the solution. The suspended solid was collected by filtration and air-dried to give the desired product (0.052 g, 0.13 mmol, 87%) as a white powder. 1 H NMR (400MHz, CDCl3)δ=7.90-7.83(m,1H),7.66-7.58(m,2H),7.53-7.49(m,2H),7.47-7.43(m,2H),2.67-2.60(m,3H)

[0298] Example 4: Synthesis of methyl 5-(1-methoxyvinyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P4)

[0299]

[0300] To bis(triphenylphosphine)palladium dichloride (II) (0.024 g, 0.034 mmol) was added a solution of 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-methyl carboxylate (0.30 g, 0.68 mmol) in toluene (5 mL). The mixture was degassed with nitrogen for 5 minutes, and then tributyl(1-methoxyvinyl)stannane (0.71 g, 2.03 mmol) was added. The reaction mixture was heated at 120 ° C for 45 minutes under microwave irradiation. The cooled reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 5%-100% ethyl acetate in cyclohexane as eluent to obtain the desired product (0.086 g, 0.20 mmol, 30%) as an off-white solid. 1 HNMR(400MHz, CDCl3)δ=7.58-7.49(m,3H),7.49-7.44(m,2H),7.43-7.37(m,1H),7.22- 7.10(m,1H),4.44-4.38(m,1H),4.27-4.21(m,1H),3.97-3.91(m,3H),3.86-3.79(m,3H)

[0301] Example 5: Synthesis of 1-(4-chlorophenyl)-5-(4-fluorophenoxy)-4-oxo-cinnoline-3-carboxylic acid (Compound P11)

[0302] Step 1: Synthesis of ethyl 3-(2,6-difluorophenyl)-3-oxo-propionate

[0303]

[0304] To a solution of 3-ethoxy-3-oxo-propionic acid potassium (6.11 g, 35.7 mmol) in acetonitrile (66 mL) at 0 ° C and under nitrogen, triethylamine (3.78 g, 37.4 mmol) and magnesium chloride (4.1 g, 42.5 mmol) were added. The reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was cooled to 0 ° C and 2,6-difluorobenzoyl chloride (3.0 g, 17 mmol) was added in batches. The reaction mixture was stirred in ice for 1.5 hours, then at room temperature for 2 hours, and then allowed to stand for 18 hours. The reaction mixture was evaporated under reduced pressure and azeotroped with toluene. The residue was suspended in ethyl acetate (50 mL) and 2M aqueous hydrochloric acid solution. These phases were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and evaporated to dryness under reduced pressure to obtain the desired crude product (mixture of tautomers) (4.5 g, 20 mmol) as a light yellow liquid. 1 H NMR (400 MHz, CDCl3) δ = 7.53-7.37 (m, 1H), 7.04-6.88 (m, 2H), 4.30-4.22 (m, 2H), 3.47-3.38 (m, 2H), 1.34-1.28 (m, 3H) (data for keto form only)

[0305] Step 2: Synthesis of ethyl (2E)-2-[(4-chlorophenyl)hydrazono]-3-(2,6-difluorophenyl)-3-oxo-propionate

[0306]

[0307] Prepared according to (2E)-3-(2-bromo-6-fluoro-phenyl)-3-oxo-2-[[4-(trifluoromethoxy)phenyl]hydrazono]propionic acid methyl ester (Example 1; Step 2) using 3-(2,6-difluorophenyl)-3-oxo-propionic acid ethyl ester (3.0 g, 9.2 mmol) and 4-chloroaniline (1.17 g, 9.2 mmol). After 2.75 hours of reaction time, the solid was collected by filtration to give the desired product as a yellow solid (2.2 g, 5.9 mmol, 64%). 1 H NMR (400MHz, CDCl3)δ=13.15-13.05(m,1H),7.44-7.32(m,1H),7.27-7.23(m,3H),7.00-6.91(m,3H),4.49-4.38(m,2H),1.51-1.39(m,3H)

[0308] Step 3: Synthesis of ethyl 1-(4-chlorophenyl)-5-fluoro-4-oxo-cinnoline-3-carboxylate

[0309]

[0310] Prepared according to 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (Example 1; Step 3) using (2Z)-2-[(4-chlorophenyl)hydrazono]-3-(2,6-difluorophenyl)-3-oxo-propionic acid ethyl ester (2.2 g, 5.9 mmol). After completion of the reaction, the cooled reaction mixture was poured onto ice and the precipitated solid was collected by filtration to give the desired product (1.8 g, 5.3 mmol, 89%) as a yellow powder. 1 H NMR (400MHz, CDCl3)δ=7.60-7.52(m,3H),7.48-7.40(m,2H),7.14-7.07(m,1H),7.00-6.87(m,1H),4.51-4.40(m,2H),1.45-1.34(m,3H)

[0311] Step 4: Synthesis of 1-(4-chlorophenyl)-5-fluoro-4-oxo-cinnoline-3-carboxylic acid

[0312]

[0313] Prepared according to the synthesis of 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Example 3) using 1-(4-chlorophenyl)-5-fluoro-4-oxo-cinnoline-3-carboxylic acid ethyl ester (1.3 g, 3.7 mmol) to give the desired product (1.15 g, 3.6 mmol, 97%) as an off-white solid. 1 H NMR (500MHz, CDCl3)δ=14.22-13.90(m,1H),7.82-7.74(m,1H),7.63-7.59(m,2H),7.51-7.37(m,2H),7.36-7.26(m,1H),7.19-7.00(m,1H)

[0314] Step 5: Synthesis of 1-(4-chlorophenyl)-5-(4-fluorophenoxy)-4-oxo-cinnoline-3-carboxylic acid

[0315]

[0316] To a solution of 1-(4-chlorophenyl)-5-fluoro-4-oxo-cinnoline-3-carboxylic acid (0.10 g, 0.31 mmol) in dimethylacetamide was added 4-fluorophenol (0.053 g, 0.47 mmol) and potassium carbonate (0.066 g, 0.47 mmol). The reaction mixture was heated at 170° C. for 45 minutes. The cooled reaction mixture was poured onto ice, and the precipitated solid was collected by filtration and then purified by mass-directed reverse phase HPLC to give the desired product (0.010 g, 0.025 mmol, 8%) as a white solid. 1 H NMR (400MHz, CDCl3)δ=7.65-7.56(m,3H),7.53-7.44(m,2H),7.20-7.06(m,4H),7.01-6.91(m,1H),6.87-6.72(m,1H)

[0317] Example 6: Synthesis of 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester and 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Compounds 1.017 and 1.018)

[0318]

[0319] A mixture of 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (0.300 g, 0.677 mmol), zinc cyanide (0.155 g, 1.32 mmol), tetrakis(triphenylphosphine)palladium (0.079 g, 0.0677 mmol) in dimethylformamide (4 mL) was heated at 160 ° C for 45 minutes under microwave irradiation. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organics were concentrated to dryness under reduced pressure. The crude residue was purified by mass-directed reverse phase HPLC to obtain 5-cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid methyl ester (0.088 g, 0.225 mmol, 33%). 1 H NMR (400 MHz, chloroform) δ=7.93-7.86 (m, 1H), 7.77-7.70 (m, 1H), 7.61-7.55 (m, 2H), 7.50-7.41 (m, 3H), 4.03-3.91 (m, 3H)

[0320] 5-Cyano-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.016 g, 0.044 mmol, 6%) was also obtained. 1H NMR (400 MHz, chloroform) δ=8.11-8.04 (m, 1H), 7.97-7.84 (m, 1H), 7.65-7.58 (m, 3H), 7.54-7.39 (m, 3H)

[0321] Example 7: Synthesis of methyl 5-(4-fluorophenyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P6)

[0322]

[0323] By 5- bromo -4- oxo -1- [4- (trifluoromethoxy) phenyl] cinnoline -3- carboxylic acid methyl ester (0.200g, 0.451mmol), (4- fluorophenyl) boronic acid (0.095g, 0.677mmol), potassium carbonate (0.126g, 0.903mmol) in acetonitrile (1.00mL) and water (0.200mL) mixture was heated at 100 DEG C for 30 minutes under microwave irradiation. The reaction mixture was diluted with 2M aqueous hydrochloric acid solution and extracted into ethyl acetate (three times). The combined organic extracts were evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 5% -100% ethyl acetate in cyclohexane as eluent to obtain the desired product (0.075g, 0.164mmol, 36%) as an off-white solid. 1 H NMR (400 MHz, chloroform) δ=7.63-7.56 (m, 3H), 7.50-7.45 (m, 2H), 7.31-7.27 (m, 3H), 7.20-7.15 (m, 1H), 7.13-7.06 (m, 2H), 3.93-3.80 (m, 3H)

[0324] Example 8: Synthesis of 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (Compound P14) and 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Compound P15)

[0325] Step 1:

[0326]

[0327] To a stirred solution of 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (50.0 mg, 0.119 mmol) in methanol (10 mL) and water (2.5 mL) at 0 ° C., sodium acetate (0.088 g, 1.07 mmol) and hydroxylamine chloride (0.074 g, 1.07 mmol) were added. The reaction mixture was stirred for 5 minutes and then heated at 80 ° C. for 6 hours. The cooled reaction mixture was poured onto ice water, neutralized with 2M aqueous hydrochloric acid solution and filtered. The filtrate 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 the desired product (0.16 g, 0.37 mmol, 34%) as an off-white solid. 1 H NMR(400MHz,DMSO-d6):10.89(s,1H),7.85(d,2H),7.72(d,3H),7.30(d,1H),7.17(d,1H),4.32(m,2H),2.04(s,3H),1.28(t,3H)

[0328] Step 2:

[0329]

[0330] To a stirred solution of 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (150 mg, 0.33 mmol) in tetrahydrofuran (6 mL) and water (2 mL) at room temperature was added lithium hydroxide monohydrate (0.055 g, 1.31 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was acidified by adding 2M aqueous hydrochloric acid solution (5 mL) and extracted into dichloromethane (x2). The combined organic extracts were washed with brine, dried over sodium sulfate and evaporated to dryness under reduced pressure to give 5-[(E)-N-hydroxy-C-methyl-carbonimido]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.098 g, 0.24 mmol, 74%) as a light brown solid. 1 H NMR(400MHz,DMSO-d6):13.9(brs,1H),10.97(s,1H),7.87(m,3H),7.72(d,2H),7.38(d,1H),7.21(d,1H),2.07(s,3H)

[0331] Example 9: Synthesis of ethyl 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P12) and 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Compound P13)

[0332] Step 1:

[0333]

[0334] To a stirred solution of 5-acetyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (1.00 g, 2.38 mmol) in tetrahydrofuran (25 mL) was added a solution of sodium methoxide (0.129 g, 2.38 mmol) and methyl 2,2-difluoroacetate (0.393 g, 3.57 mmol) in methanol. The reaction mixture was stirred at room temperature for 10 hours. The reaction mixture was quenched by adding 1 M aqueous hydrochloric acid solution and extracted into ethyl acetate. The organic extract was evaporated to dryness under reduced pressure to give a crude product (0.900 g, 1.91 mmol, 80%) as a brown solid.

[0335] Step 2:

[0336]

[0337] To a stirred solution of 5-(4,4-difluoro-3-oxo-butyryl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.650 g, 1.38 mmol) in ethanol (5.30 mL) was added 1 M aqueous sodium hydroxide solution (0.75 mL) followed by hydroxylamine hydrochloride (0.144 g, 2.07 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with brine, extracted into ethyl acetate, and the combined organic extracts were evaporated to dryness under reduced pressure to give 5-[5-(difluoromethyl)-5-hydroxy-4H-isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.600 g, 1.24 mmol, 90%).

[0338] Step 3:

[0339]

[0340] To a stirred solution of 5-[5-(difluoromethyl)-5-hydroxy-4H-isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.600 g, 1.11 mmol) in toluene (10 mL) was added sodium p-toluenesulfonate (0.019 g, 0.11 mmol). The reaction mixture was stirred at 110 ° C for 3 hours. The reactant was evaporated to dryness under reduced pressure, and the residue was partitioned between water and ethyl acetate. The organic extract was washed with brine and evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 40%-50% ethyl acetate in hexane to give 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.110 g, 0.235 mmol, 21%). 1 H NMR(400MHz,DMSO-d6):13.78(s,1H),7.91(m,3H),7.77(m,3H),7.75(m,2H),7.05(d,1H)

[0341] Step 4:

[0342]

[0343] To a stirred solution of 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.250 g, 0.535 mmol) in ethanol (25 mL) at room temperature was added concentrated sulfuric acid (0.105 g, 1.07 mmol). The reaction mixture was heated at 75 ° C. for 6 hours with stirring. The reaction mixture was evaporated to dryness under reduced pressure. The crude residue was diluted with cold water, neutralized with saturated aqueous sodium bicarbonate solution and extracted into ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure to give ethyl 5-[5-(difluoromethyl)isoxazol-3-yl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (0.120 g, 0.237 mmol, 44%) as a brown semi-solid. 1 H NMR (400MHz, DMSO-d6):7.86(s,1H),7.71(d,2H),7.61(m,3H),7.41(m,2H),7.03(s,1H),4.29(t,2H),1.29(q,3H)

[0344] Example 10: Synthesis of 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid ethyl ester (Compound P16) and 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid (Compound P17)

[0345] Step 1:

[0346]

[0347] To a stirred solution of 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (1.80 g, 3.94 mmol) in toluene (30 mL) at room temperature was added tributyl(vinyl)tin (1.87 g, 5.91 mmol). The mixture was purged with argon for 5 minutes, then bis(triphenylphosphine)palladium dichloride (II) (0.287 g, 0.394 mmol) was added and purged with argon again for 5 minutes. The reaction mixture was heated at 110 ° C for 4 hours in a sealed test tube. The cooled reaction mixture was filtered through a celite pad and the filtrate was evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using 10% ethyl acetate in hexanes as eluent to give 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid ethyl ester (1.30 g, 3.05 mmol, 78%) as an off-white solid. 1 H NMR (400MHz, CDCl3): 8.14(m,1H),7.56(m,3H),7.53(d,3H),7.08(d,1H),5.65(d,1H),5.47(d,1H),4.47(q,2H),1.42(t,3H)

[0348] Step 2:

[0349]

[0350] To a stirred solution of 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid ethyl ester (150 mg, 0.352 mmol) in a mixture of tetrahydrofuran (3 mL) and water (2 mL) at room temperature was added lithium hydroxide monohydrate (0.059 g, 1.41 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was acidified by adding 2M aqueous hydrochloric acid solution and extracted into dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure to give 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid (0.098 g, 0.247 mmol, 70%) as an off-white solid. 1H NMR(400MHz,DMSO-d6):14.08(s,1H),8.04(m,1H),7.79(m,2H),7.72(m,1H),7.64(m,2H),7.55(m,1H),7.18(d,1H),5.79(d,1H),5.74(d,1H)

[0351] Example 11: Synthesis of ethyl 4-oxo-5-(2-oxoethyl)-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P18)

[0352] Step 1:

[0353]

[0354] To a stirred solution of 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (0.200 g, 0.394 mmol) in toluene (4 mL) was added bis(triphenylphosphine)palladium dichloride (II) (0.0287 g, 0.0394 mmol). The mixture was degassed under argon for 5 minutes, followed by the addition of tributyl(1-ethoxyvinyl)stannane (0.178 mL, 0.492 mmol). The reaction mixture was heated at 110 ° C for 3 hours. The cooled reaction mixture was filtered through a celite pad and the filtrate was evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using 20% ethyl acetate in hexane as eluent to obtain 5-[(E)-2-ethoxyvinyl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (0.080 g, 0.178 mmol, 45%).

[0355] Step 2:

[0356]

[0357] To a stirred solution of 5-[(E)-2-ethoxyvinyl]-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (50%, 2.00 g, 2.23 mmol) in acetone (10 mL) was added 2M aqueous hydrochloric acid solution (5.00 g). The reaction mixture was stirred for 5 minutes and then heated at 65 ° C for 16 hours. The cooled reactant was evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using 3% methanol in dichloromethane as eluent to give 4-oxo-5-(2-oxoethyl)-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (0.200 g, 0.466 mmol, 21%) as a brown solid. 1H NMR (400MHz, DMSO-d6):9.76(s,1H),7.87(t,2H),7.74(m,3H),7.38(d,1H),7.12(d,1H),4.30(m,4H),1.29(m,3H)

[0358] Example 12: Synthesis of 5-(4-chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (Compound P32) and 5-(4-chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Compound P19)

[0359] Step 1:

[0360]

[0361] To a solution of ethyl 5-fluoro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (0.500 g, 1.26 mmol) in N,N-dimethylformamide (5 mL) at 0 ° C and under argon was added potassium carbonate (124 mg, 1.26 mmol) followed by 4-chloro-1H-pyrazole (0.194 g, 1.89 mmol). The reaction mixture was stirred at 110 ° C for 5 hours. The cooled reaction mixture was poured into water and extracted into ethyl acetate. The combined organic extracts were washed with water and then with brine, dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 0% to 50% ethyl acetate in hexanes as eluent to give ethyl 5-(4-chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (450 mg, 0.921 mmol, 73%) as a light brown solid. 1 H NMR (400MHz, DMSO-d6):8.21(s,1H),7.87(m,4H),7.82(d,2H),7.56(d,1H),7.28(m,1H),4.29(d,2H),1.27(t,3H)

[0362] Step 2:

[0363]

[0364] To a stirred solution of ethyl 5-(4-chloro-2H-pyrrol-2-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (180 mg, 0.358 mmol) in a mixture of tetrahydrofuran (5 mL) and water (1.5 mL) at room temperature was added lithium hydroxide monohydrate (0.060 g, 1.43 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was acidified with 2M aqueous hydrochloric acid solution (2 mL) and extracted into dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure to give 5-(4-chloropyrazol-1-yl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid as a yellow solid; (0.110 g, 0.245 mmol, 68%). 1 H NMR(400MHz,DMSO-d6):13.81(t,1H),8.24(s,1H),7.91(m,4H),7.72(m,2H),7.62(d,1H),7.36(d,1H)

[0365] Example 13: Synthesis of ethyl 5-(cyanomethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P35)

[0366]

[0367] A stirred solution of ethyl 5-bromo-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (0.100 g, 0.197 mmol) in mesitylene (10 mL) was degassed with argon for 5 minutes, followed by the addition of potassium (2-cyanoacetyl)oxy (0.082 mL, 0.295 mmol), allylpalladium chloride (ii) dimer (0.0144 g, 0.0394 mmol) and 2-dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl (0.0484 g, 0.118 mmol). The reaction mixture was purged under argon for 2 minutes and then heated at 100° C. in a sealed test tube for 5 hours. The cooled reaction mixture was filtered through celite and the filtrate was evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 20% to 30% ethyl acetate in hexanes as eluent to give ethyl 5-(cyanomethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (0.050 g, 0.120 mmol, 61%). 1H NMR (400MHz, DMSO-d6):7.86(d,2H),7.79(m,1H),7.74(d,2H),7.65(d,1H),7.29(d,1H),4.59(s,2H),4.35(q,2H),1.30(t,3H)

[0368] Example 14: Synthesis of ethyl 5-(difluoromethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (Compound P36)

[0369] Step 1:

[0370]

[0371] To a stirred solution of 4-oxo-1-[4-(trifluoromethoxy)phenyl]-5-vinyl-cinnoline-3-carboxylic acid ethyl ester (0.600 g, 1.41 mmol) in a mixture of tetrahydrofuran (20 mL) and water (5 mL) at 0° C., sodium periodate (0.905 g, 4.23 mmol) and potassium osmate dihydrate (0.052 g, 0.141 mmol) were added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched and extracted into ethyl acetate by adding 10% aqueous sodium thiosulfate solution. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using 30% ethyl acetate in hexanes as eluent to give ethyl 5-formyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylate (0.455 g, 1.06 mmol, 76%) as an off-white solid.

[0372] Step 2:

[0373]

[0374] To a stirred solution of 5-formyl-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (300mg, 0.70mmol) in dichloromethane (20mL) at 0°C, diethylamino sulfur trifluoride (0.565g, 3.51mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched and extracted into dichloromethane by adding saturated sodium bicarbonate aqueous solution. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using 20% ethyl acetate in hexane as eluent to obtain 5-(difluoromethyl)-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (0.290g, 0.64mmol, 92%) as a white solid.1 H NMR(400MHz, CDCl3):8.22(s,2H),7.93(t,1H),7.73(t,2H),7.45(d,2H),7.32(s,1H),4.45(q,2H),1.41(t,3H)

[0375] Example 15: Synthesis of 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (Compound P39) and 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (Compound P40)

[0376] Step 1:

[0377]

[0378] To the stirred solution of ethyl malonate potassium salt (8.36g, 49.1mmol) in acetonitrile (150mL) at room temperature, add 2-fluoro-6-nitro-benzoyl chloride (5.00g, 24.6mmol), magnesium chloride (5.85g, 61.4mmol) and triethylamine (5.47g, 54.0mmol) successively.Reactant mixture is stirred at room temperature 16 hours.Residue is suspended in ethyl acetate and 2M aqueous hydrochloric acid solution.Each phase is separated, and aqueous phase is extracted into ethyl acetate (x2).By the organic extract merged through dried over sodium sulfate, filter, and be evaporated under reduced pressure to dryness, to obtain the crude product in light yellow liquid.

[0379] Step 2:

[0380]

[0381] To the stirred solution of 4-(trifluoromethoxy) aniline (3.50g, 19.8mmol) in 2M aqueous hydrochloric acid solution (10mL) at 0 ℃, dropwise add solution of sodium nitrite (1.49g, 21.6mmol) in water (5mL).Reaction mixture was stirred 0.5 hour, then dropwise add in cooling (0 ℃) solution of 3-(2-fluoro-6-nitro-phenyl)-3-oxo-ethyl propionate (5.10g, 18.0mmol) and potassium acetate (8.81g, 89.9mmol) in water (50mL).Reaction mixture was stirred at 0 ℃ for 2 hours and then it was heated to room temperature.Reaction mixture was diluted with water and extracted in ethyl acetate (x2). The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure to give crude ethyl (2Z)-3-(2-fluoro-6-nitro-phenyl)-3-oxo-2-[[4-(trifluoromethoxy)phenyl]hydrazono]propanoate (5.00 g, 11.3 mmol, 63%) as a red liquid.

[0382] Step 3:

[0383]

[0384] To a stirred solution of (2Z)-3-(2-fluoro-6-nitro-phenyl)-3-oxo-2-[[4-(trifluoromethoxy)phenyl]hydrazono]propionic acid ethyl ester (8.00 g, 16.2 mmol) in N,N-dimethylformamide (80 mL) was added potassium carbonate (4.42 g, 32.5 mmol). The reaction mixture was heated at 100 ° C for 4 hours. The cooled reaction mixture was diluted with cold water and extracted into ethyl acetate (x2). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using 20% ethyl acetate in hexane as eluent to obtain 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (7.00 g, 15.9 mmol, 98%) as a light orange solid. 1 H NMR(400MHz,DMSO-d6):7.95(m,4H),7.75(d,2H),7.36(m,1H),4.39(q,2H),1.23(t,3H)

[0385] Step 4:

[0386]

[0387] To a stirred solution of 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid ethyl ester (0.200g, 0.449mmol) in a mixture of tetrahydrofuran (10mL) and water (5mL) at room temperature, lithium hydroxide monohydrate (0.075g, 1.80mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was acidified with 2M aqueous hydrochloric acid solution and extracted into dichloromethane (x2). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure to obtain 5-nitro-4-oxo-1-[4-(trifluoromethoxy)phenyl]cinnoline-3-carboxylic acid (0.120g, 0.301mmol, 67%) as a yellow solid. 1 H NMR(400MHz,DMSO-d6):13.67(s,1H),7.89(m,4H),7.72(d,2H),7.39(d,1H)

[0388] Table 2: The selected compounds in Table 1 1 H NMR and LC / MS data.

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410] Biological Examples

[0411] Seeds of various test species were sown in standard soil in pots (Amaranthus retoflexus (AMARE), Solanum nigrum (SOLNI), Setaria faberi (SETFA), Lolium perenne (LOLPE), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE). After cultivation for 8 days under controlled conditions in a greenhouse (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 active ingredient in acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5). Unless otherwise stated, the compound was applied at 1000 g / ha. These test plants were then grown in a greenhouse under controlled conditions (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 caused to the plants by the test was evaluated. The following table shows the biological activity on a five-point scale (5 = 81%-100%; 4 = 61%-80%; 3 = 41%-60%; 2 = 21-40%; 1 = 10-20%; 0 = 0%; - = not tested).

[0412] Table B1: Pre-emergence Test

[0413]

[0414]

[0415] Table B2: Post-emergence testing

[0416]

[0417]

Claims

1. A compound having formula (I): in, X is O; R 1 is optionally replaced by 1 or 2 R 7 A phenyl group substituted with R 2 is cyano, C1-C3 alkylcarbonyl, C1-C3 alkoxy C2-C3 alkenyl, or -CR 11 =N-OR 10 ; R 3 It is hydrogen; R 4 、R 5 , and R 6 It's all hydrogen; R 7 is chlorine, cyano, methyl, trifluoromethyl, trifluoromethoxy, methylsulfanyl, or any two adjacent R 7 The groups together with the carbon atom to which they are attached form a quinolinyl, indazolyl, 1,3-benzoxadiazolyl, or 1,4-benzodioxinyl group, and wherein the quinolinyl, indazolyl, 1,3-benzoxadiazolyl, or 1,4-benzodioxinyl group may be optionally replaced by 1, 2, 3, or 4 groups which may be the same or different and are represented by R 9 The group represented by substituted; R 9 is fluorine or methyl; R 10 and R 11 are each independently selected from hydrogen and C1-C3 alkyl; or a salt thereof.

2. The compound according to claim 1, wherein R 1 is optionally replaced by a single R 7 The group represents a phenyl group substituted with .

3. The compound according to claim 1 or claim 2, wherein R 2 It is a cyano group, an acetyl group, a 1-methoxyvinyl group, a 1-ethoxyvinyl group, or an N-methoxy-C-methylcarbonimido group.

4. The compound according to claim 1 or claim 2, wherein R 10 and R 11 are each independently selected from hydrogen, methyl and ethyl.

5. The compound according to claim 2, wherein R 7 It is trifluoromethoxy.

6. A herbicidal composition comprising the compound according to any one of claims 1 to 5 and an agriculturally acceptable formulation adjuvant.

7. The herbicidal composition according to claim 6, further comprising at least one additional pesticide.

8. The herbicidal composition according to claim 7, wherein The additional pesticide is a herbicide.

9. The herbicidal composition according to claim 6, further comprising a herbicide safener.

10. A method of controlling the growth of unwanted plants, which comprises applying a compound of formula (I) according to any one of claims 1 to 5 or a herbicidal composition according to any one of claims 6 to 9 to the unwanted plants or the locus thereof.

11. Use of a compound of formula (I) according to any one of claims 1 to 6 as a herbicide.

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