Herbicidal compounds

Abstract

Disclosed are compounds of formula (I) wherein the substituents are as defined in claim 1, which can be used as pesticidal agents, in particular as herbicides. # imgabs0 #

Description

[0001] The present invention relates to compounds having herbicidal activity, and to processes and intermediates for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, and to the use of such compounds and compositions for controlling undesirable vegetation in crops of useful plants: in particular for controlling weeds.

[0002] US 2014 / 048827, WO 2016 / 120116 and WO 2020 / 239607 describe herbicidal derivatives.

[0003] The present invention is based on the following discovery: the compound of formula (I) as defined herein exhibits unexpectedly good herbicidal activity. Therefore, according to the present invention, there is provided a compound of formula (I) or an agronomically acceptable salt thereof:

[0004]

[0005] in

[0006] X 1 Yes CR 1 , nitrogen or N + -O - ;

[0007] X 2 Yes CR 17 or nitrogen;

[0008] X 3 Yes CR 18 or nitrogen;

[0009] X 4 Yes CR 19 or nitrogen;

[0010] The premise is X 1 , X 2 , X 3 and X 4 At most two of them are nitrogen, and X 3 and X 4 Both are not nitrogen;

[0011] Y is CH or nitrogen;

[0012] B is O, S or NR 5 ;

[0013] D is -[C(R 6 )(R 7 )] n -;

[0014] m is an integer from 0 to 2;

[0015] n is an integer from 1 to 4;

[0016] R 1 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 ;

[0017] R 2 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl acyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, CO2R 9 or CONR 10 R 11 ;or

[0018] R 1 and R 2 Together with the carbon atom to which they are attached, they form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and may optionally contain one or two heteroatoms selected from nitrogen, oxygen and sulfur and may be replaced by 1 to 4 residues consisting of R 16or

[0019] R 2 and R 19 Together with the carbon atom to which they are attached, they form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and may optionally contain one or two heteroatoms selected from nitrogen, oxygen and sulfur and may be replaced by 1 to 4 residues consisting of R 16 The group represented by is substituted;

[0020] R 3 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio or C1-C4 alkylsulfonyl;

[0021] R 4 is hydrogen, halogen, cyano, nitro, aminocarbonyl, aminothiocarbonyl, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkylsulfonyl;

[0022] R 5 is hydrogen, hydroxy, C1-C6 alkyl or C1-C4 alkoxy;

[0023] R 6 and R 7 are each independently hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, hydroxy, C1-C4 alkoxy, C1-C4 alkoxycarbonyl or CH2OR 12 ; The premise is R 6 and R 7 Not all hydroxyl groups are on the same carbon atom;

[0024] Alternatively, two R on the same carbon atom or on different carbon atoms 6 and R 7 The groups together form a C1-C5 alkylene chain containing 0, 1 or 2 oxygen atoms, separated by 1 to 3 R 15 The group represented by is substituted;

[0025] Alternatively, two R 6 and R 7 The groups together form C2-C3 alkenes;

[0026] R 8 Yes OR 9 , SR 9 or NR 10 R 11 ;

[0027] R 9 is hydrogen, C1-C 10 Alkyl, C1-C10 Halogenated alkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C6-C 10 Aryl C1-C3 alkyl, 1 to 4 R 13 The group substituted C6-C 10 Aryl C1-C3 alkyl, heteroaryl C1-C3 alkyl, or 1 to 3 R 13 A group representing a substituted heteroaryl C1-C3 alkyl group;

[0028] R 10 is hydrogen, C1-C6 alkyl, SO2R 14 ;

[0029] R 11 is hydrogen or C1-C6 alkyl; or

[0030] R 10 and R 11 together with the nitrogen to which they are attached, form a 3- to 6-membered heterocyclyl ring;

[0031] R 12 is hydrogen, C1-C4 alkyl or C1-C4 alkylcarbonyl;

[0032] R 13 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano or C1-C4 alkylsulfonyl;

[0033] R 14 is C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkyl(C1-C4 alkyl)amino;

[0034] R 15 is hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl;

[0035] R 16 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano or C1-C4 alkylsulfonyl;

[0036] R 17is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 ;

[0037] R 18 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 ;

[0038] R 19is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 ;

[0039] R 20 and R 21 are each independently hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C4 alkoxy or -CH2OR 12 ;

[0040] Or two R 20 and R 21 The groups together with the carbon atoms to which they are attached form a C2-C5 alkylene chain, wherein the C2-C5 alkylene chain contains 0, 1 or 2 oxygen atoms, and wherein the C2-C5 alkylene chain is substituted by 1 to 3 R 15 The group represented by is substituted;

[0041] Or two R 20 and R 21 The groups, together with the carbon atom to which they are attached, form a C2-C3 alkene; and

[0042] The premise is R 1 , R 2 , R 17 , R 18 and R 19 Not all hydrogen.

[0043] 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) and an agrochemically acceptable diluent or carrier. Such an agricultural composition may further comprise at least one additional active ingredient.

[0044] According to a third aspect of the present invention, there is provided a method for controlling or preventing the growth of unwanted plants, wherein a herbicidally effective amount of a compound of formula (I) or a composition comprising such a compound as an active ingredient is applied to the plants, parts thereof or the locus thereof.

[0045] According to a fourth aspect of the present invention, there is provided use of a compound of formula (I) as a herbicide.

[0046] According to a fifth aspect of the present invention, there is provided a method for preparing a compound of formula (I).

[0047] When substituents are indicated as being "optionally substituted", this means that they may or may not carry one or more identical or different substituents, for example one, two or three R 13 Substituents. For example, C1-C6 alkyl substituted with 1, 2 or 3 halogens may include, but are not limited to -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, C1-C6 alkoxy substituted with 1, 2 or 3 halogens may include, but are not limited to CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O- or CH3CF2O- groups.

[0048] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.

[0049] As used herein, "cyano" refers to a -CN group.

[0050] As used herein, "amino" means a -NH2 group.

[0051] As used herein, "hydroxyl" means an -OH group.

[0052] As used herein, "nitro" means a -NO2 group.

[0053] As used herein, the term "C1-C 10 "Alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to ten carbon atoms, and attached to the remainder of the molecule by a single bond. C1-C6 alkyl, C1-C4 alkyl, C1-C3 alkyl and C1-C2 alkyl should be interpreted accordingly. C1-C 10Examples of alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1-dimethylethyl (tert-butyl).

[0054] As used herein, the term "C1-C4 alkoxy" refers to a group having the formula -OR a A group in which R a is C as defined above 1- C4 alkyl. C1-C3 alkoxy should be interpreted accordingly. 1-4 Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, and tert-butoxy.

[0055] As used herein, the term "C1-C 10 "Haloalkyl" refers to a C1-C12 group as generally defined above substituted by one or more halogen atoms which may be the same or different. 10 Alkyl groups. C1-C6 haloalkyl and C1-C4 haloalkyl should be interpreted accordingly. 10 Examples of haloalkyl include, but are not limited to, chloromethyl, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, and 2,2,2-trifluoroethyl.

[0056] 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. C3-C6 alkenyl, C2-C4 alkenyl and C2-C3 alkenyl should be interpreted accordingly. 2- Examples of C6 alkenyl groups include, but are not limited to, prop-1-enyl, allyl (prop-2-enyl), and but-1-enyl.

[0057] As used herein, the term "C2-C6 haloalkenyl" refers to a C2-C6 alkenyl group as generally defined above that is substituted with one or more identical or different halogen atoms. C3-C6 haloalkenyl, C2-C4 haloalkenyl, and C2-C3 haloalkenyl should be interpreted accordingly. Examples of C2-C6 haloalkenyl groups include, but are not limited to, vinyl chloride, vinyl fluoride, 1,1-difluoroethylene, 1,1-dichloroethylene, and 1,1,2-trichloroethylene.

[0058] As used herein, the term "C2-C6 alkynyl" refers to a straight or branched hydrocarbon chain radical consisting only of carbon atoms and hydrogen atoms, which contains at least one triple bond, has from two to six carbon atoms, and is attached to the remainder of the molecule by a single bond. C2-C4 alkynyl and C3-C6 alkynyl should be interpreted accordingly. Examples of C2-C6 alkynyl include, but are not limited to, prop-1-ynyl, propargyl (prop-2-ynyl) and but-1-ynyl.

[0059] As used herein, the term "C1-C6 haloalkoxy" refers to a C1-C6 alkoxy group as defined above that is substituted with one or more identical or different halogen atoms. C1-C4 haloalkoxy should be interpreted accordingly. Examples of C1-C6 haloalkoxy include, but are not limited to, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy, and trifluoroethoxy.

[0060] As used herein, the term "C1-C4 haloalkoxy C1-C6 alkyl" refers to a b -OR a - a group, wherein R b is a C1-C4 haloalkyl group as generally defined above, and R a is a C1-C6 alkylene group as generally defined above.

[0061] As used herein, the term "C1-C4 alkoxy C1-C6 alkyl" refers to a b -OR a - a group, wherein R b is a C1-C4 alkyl group as generally defined above, and R a is a C1-C6 alkylene group as generally defined above.

[0062] As used herein, the term "C1-C4 alkoxy" refers to a b -OR a -O- group, where R b is a C1-C4 alkyl group as generally defined above, and R a is a C1-C4 alkylene group as generally defined above.

[0063] As used herein, the term "C1-C6 alkylcarbonyl" refers to a group having the formula -C(O)R a A group in which R a is a C1-C6 alkyl group as generally defined above. Examples of C1-C6 alkylcarbonyl groups include, but are not limited to, acetyl.

[0064] As used herein, the term "C1-C6 alkoxycarbonyl" refers to a group having the formula -C(O)OR a A group in which R a is a C1-C6 alkyl group as generally defined above.

[0065] As used herein, the term "C1-C4 alkylamino" refers to a a NH-group, where R a is a C1-C4 alkyl group as generally defined above.

[0066] As used herein, the term "di(C1-C4 alkyl)amino" refers to a a )(R b ) group, wherein R a and R b Each individually is a C1-C4 alkyl group as generally defined above. The term "di(C1-C3 alkyl)amino" should be interpreted accordingly.

[0067] As used herein, the term "C1-C4 alkylcarbonylamino" refers to a group having the formula -C(O)NHR a A group in which R a is a C1-C4 alkyl group as generally defined above.

[0068] As used herein, the term "C1-C4 alkylcarbonyl (C1-C4 alkyl)amino" refers to a group having the formula -NH(R a )C(O)R b A group in which R a and R b Each is independently a C1-C4 alkyl group as generally defined above.

[0069] As used herein, the term "C1-C4 alkoxycarbonylamino" refers to a group having the formula -NHC(O)OR a A group in which R a is a C1-C4 alkyl group as generally defined above.

[0070] As used herein, the term "aminocarbonyl" refers to a group having the formula -C(O)NH2.

[0071] As used herein, the term "aminocarbonylamino" refers to a group having the formula -NHC(O)H2.

[0072] As used herein, the term "aminothiocarbonyl" refers to a group having the formula -C(S)NH2.

[0073] As used herein, the term "C1-C4 alkylaminocarbonylamino" refers to a alkylaminocarbonylamino group having the formula -NHC(O)NHR a A group in which R a is a C1-C4 alkyl group as generally defined above.

[0074] As used herein, the term "C1-C4 alkylsulfonylamino" refers to a group having the formula -NHS(O)2R a A group in which R a is a C1-C4 alkyl group as generally defined above.

[0075] As used herein, the term "C1-C4 haloalkylsulfonylamino" refers to a group having the formula -NHS(O)2Ra A group in which R a is a C1-C4 haloalkyl group as generally defined above.

[0076] As used herein, the term "C1-C4 alkylthio" refers to a group having the formula -SR a A group in which R a is a C1-C4 alkyl group as generally defined above. The terms "C1-C3 alkylsulfanyl" and "C1-C2 alkylsulfanyl" should be interpreted accordingly. Examples of C1-C4 alkylsulfanyl include, but are not limited to, methylsulfanyl.

[0077] As used herein, the term "C1-C4 haloalkylthio" refers to a group having the formula -SR a A group in which R a is a C1-C4 haloalkyl group as generally defined above.

[0078] As used herein, the term "C1-C4 alkylsulfinyl" refers to a group having the formula -S(O)R a A group in which R a is a C1-C4 alkyl group as generally defined above. The terms "C1-C3 alkylsulfinyl" and "C1-C2 alkylsulfinyl" should be interpreted accordingly. Examples of C1-C4 alkylsulfinyl include, but are not limited to, methylsulfinyl.

[0079] As used herein, the term "C1-C4 alkylsulfonyl" refers to a group having the formula -S(O)2R a A group in which R a is a C1-C4 alkyl group as generally defined above. The terms "C1-C3 alkylsulfonyl" and "C1-C2 alkylsulfonyl" should be interpreted accordingly. Examples of C1-C4 alkylsulfonyl include, but are not limited to, methylsulfonyl.

[0080] As used herein, the term "C1-C4 alkylsulfonyloxy" refers to a alkylsulfonyloxy group having the formula -OS(O)2R a A group in which R a is a C1-C4 alkyl group as generally defined above.

[0081] As used herein, the term "C1-C4 haloalkylsulfonyloxy" refers to a a A group in which R a is a C1-C4 haloalkyl group as generally defined above.

[0082] As used herein, the term "C1-C4 haloalkylsulfinyl" refers to a group having the formula -S(O)R a A group in which R ais a C1-C4 haloalkyl group as generally defined above.

[0083] As used herein, the term "C1-C4 haloalkylsulfonyl" refers to a group having the formula -S(O)2R a A group in which R a is a C1-C4 haloalkyl group as generally defined above.

[0084] As used herein, the term "C3-C6 cycloalkyl" refers to a stable monocyclic group that is saturated or partially unsaturated and contains 3 to 6 carbon atoms. C3-C4 cycloalkyl should be interpreted accordingly. Examples of C3-C6 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0085] As used herein, the term "C6-C 10 "Aryl" refers to a 6- to 10-membered aromatic ring system consisting solely of carbon and hydrogen atoms, which may be monocyclic, bicyclic or tricyclic. Examples of such ring systems include phenyl, naphthyl, or indenyl.

[0086] As used herein, the term "C6-C 10 "Aryl C1-C3 alkyl" refers to an aryl moiety as generally defined above, attached to the remainder of the molecule via a C1-C3 alkylene linker as defined above.

[0087] As used herein, unless otherwise expressly stated, the term "heteroaryl" refers to a 5- or 6-membered monocyclic aromatic ring containing 1, 2, 3 or 4 heteroatoms selected individually from nitrogen, oxygen and sulfur. The heteroaryl group may be bonded to the remainder of the molecule via a carbon atom or a heteroatom. Examples of heteroaryl groups include furanyl, pyrrolyl, imidazolyl, thienyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl or pyridyl.

[0088] As used herein, unless expressly stated otherwise, the term "heteroaryl C1-C3 alkyl" refers to a heteroaryl moiety as generally defined above attached to the remainder of the molecule via a C1-C3 alkylene linker as defined above.

[0089] As used herein, unless otherwise expressly stated, the term "heterocyclyl" or "heterocyclic" refers to a stable 4- to 6-membered non-aromatic monocyclic group containing 1, 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur. The heterocyclyl group may 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, pyrrolinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidinyl, piperazinyl, tetrahydropyranyl, dihydroisoxazolyl, dioxolanyl, morpholinyl or δ-lactamyl.

[0090] The presence of one or more possible asymmetric carbon atoms in a compound with formula (I) means that the compound can exist in the form of chiral isomers, i.e., enantiomers or diastereomers. 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 with formula (I). Similarly, formula (I) is intended to include all possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) (when present). The present invention includes all possible tautomeric forms of compounds with formula (I). Similarly, in the presence of disubstituted olefins, these can exist in E or Z form or as a mixture of the two in any ratio. The present invention includes all these possible isomeric forms and mixtures thereof of compounds with formula (I).

[0091] The compound of formula (I) is generally provided in the form of an agronomically acceptable salt, zwitterion or an agronomically acceptable zwitterionic salt. The present invention encompasses all such agronomically acceptable salts, zwitterions and mixtures thereof in all ratios.

[0092] Suitable agronomically acceptable salts of the present invention may have cations including, but not limited to, metals, conjugate acids of amines, and organic cations. Examples of suitable metals include aluminum, calcium, cesium, copper, lithium, magnesium, manganese, potassium, sodium, iron, and zinc. Examples of suitable amines include allylamine, ammonia, amylamine, arginine, phenethylbenzylamine, benzathine, butenyl-2-amine, butylamine, butylethanolamine, cyclohexylamine, decylamine, diamylamine, dibutylamine, diethanolamine, diethylamine, diethylenetriamine, diheptylamine, dihexylamine, diisoamylamine, diisopropylamine, dimethylamine, dioctylamine, dipropanolamine, dipropargylamine, dipropylamine, dodecylamine, ethanolamine, ethylamine, ethylbutylamine, ethylenediamine, ethylheptylamine, ethyloctylamine, ethylpropanolamine, heptadecanamine, heptylamine, hexadecylamine, hexenyl-2-amine, hexylamine, hexylheptylamine, hexyloctylamine, histidine, indoline, isoamylamine, isobutanolamine, isobutylamine, isopropanolamine, isopropylamine , lysine, meglumine, methoxyethylamine, methylamine, methylbutylamine, methylethylamine, methylhexylamine, methylisopropylamine, methylnonylamine, methyloctadecylamine, methylpentadecylamine, morpholine, N,N-diethylethanolamine, N-methylpiperazine, nonylamine, octadecylamine, octylamine, oleylamine, pentadecylamine, pentenyl-2-amine, phenoxyethylamine, picoline, piperazine, piperidine, propanolamine, propylamine, propylenediamine, pyridine, pyrrolidine, sec-butylamine, stearamide, tallowamine, tetradecylamine, tributylamine, tridecylamine, trimethylamine, triheptylamine, trihexylamine, triisobutylamine, triisodecylamine, triisopropylamine, trimethylamine, tripentylamine, tripropylamine, tris(hydroxymethyl)aminomethane, and undecylamine. Examples of suitable organic cations include benzyltributylammonium, benzyltrimethylammonium, benzyltriphenylphosphonium, choline, tetrabutylammonium, tetrabutylphosphonium, tetraethylammonium, tetraethylphosphonium, tetramethylammonium, tetramethylphosphonium, tetrapropylammonium, tetrapropylphosphonium, tributylsulfonium, tributylsulfoxide, triethylsulfonium, triethylsulfoxide, trimethylsulfonium, trimethylsulfoxide, tripropylsulfonium, and tripropylsulfoxide.

[0093] The following list provides information on substituents X of compounds of formula (I) according to the present invention. 1 , X 2 , X 3 , X 4 , Y, B, D, m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R16 , R 17 , R 18 , R 19 , R 20 and R 21 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.

[0094] X 1 Yes CR 1 , nitrogen or N + -O - , preferably CR 1 or N + -O - , and more preferably CR 1 .

[0095] X 2 Yes CR 17 or nitrogen, preferably nitrogen.

[0096] X 3 Yes CR 18 or nitrogen, preferably CR 18 .

[0097] X 4 Yes CR 19 or nitrogen, preferably CR 19 .

[0098] Preferably, the premise is that X 2 , X 3 and X 4 At most one of them is nitrogen, more preferably provided that X 2 , X 3 and X 4 One of them is nitrogen.

[0099] Y is CH or nitrogen. Preferably, Y is CH.

[0100] B is O, S or NR 5 Preferably, B is O, NH or NCH3, more preferably, B is O or NH.

[0101] m is an integer from 0 to 2. Preferably, m is 0 or 2, more preferably, m is 0.

[0102] n is an integer from 1 to 4. Preferably, n is an integer from 1 to 2, more preferably, n is 2.

[0103] R 1is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 Preferably, R 1 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, more preferably hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl, most preferably R 1 is hydrogen, fluorine, chlorine, methyl or trifluoromethyl. In one embodiment, R 1 is halogen, preferably chlorine.

[0104] R 2 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl acyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, CO2R 9 or CONR 10 R 11 Preferably, R 2is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, more preferably hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl, most preferably hydrogen, fluorine, chlorine, methyl or trifluoromethyl. Still more preferably, R 2 is hydrogen; or

[0105] R 2 and R 19 Together with the carbon atom to which they are attached, they form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and may optionally contain one or two heteroatoms selected from nitrogen, oxygen and sulfur and may be replaced by 1 to 4 residues consisting of R 16 Preferably, R 2 and R 19 Together with the carbon atom to which they are attached, they form a 5-membered saturated ring, which optionally contains one or two oxygen atoms and may be replaced by one or two R 16 The group represented is substituted.

[0106] R 3 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio or C1-C4 alkylsulfonyl. 3 is hydrogen, chlorine or fluorine, more preferably hydrogen or fluorine. Even more preferably, R 3 It's fluorine.

[0107] R 4 is hydrogen, halogen, cyano, nitro, aminocarbonyl, aminothiocarbonyl, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkylsulfonyl. 4 is hydrogen, chlorine, bromine, cyano or aminothiocarbonyl, more preferably chlorine, bromine or cyano, still more preferably chlorine or bromine. Even more preferably, R 4 It's chlorine.

[0108] R 5 is hydrogen, hydroxy, C1-C6 alkyl or C1-C4 alkoxy. 5 It's hydrogen.

[0109] R 6 and R 7 are each independently hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, hydroxy, C1-C4 alkoxy, C1-C4 alkoxycarbonyl or -CH2OR 12 ; The premise is R 6 and R 7 Not all hydroxyl groups are on the same carbon atom, or two R groups are on the same carbon atom or on different carbon atoms.6 and R 7 The groups together form a C1-C5 alkylene chain containing 0, 1 or 2 oxygen atoms, separated by 1 to 3 R 15 or, two R on the same carbon atom 6 and R 7 The groups together form a C2-C3 olefin. Preferably, R 6 and R 7 Each is independently hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxycarbonyl, more preferably hydrogen, halogen or C1-C2 alkyl, still more preferably hydrogen, chlorine or methyl. Even more preferably, R 6 and R 7 Each independently is hydrogen or methyl. In a particularly preferred embodiment, R 6 and R 7 Both are hydrogen.

[0110] R 8 Yes OR 9 , SR 9 or NR 10 R 11 Preferably, R 8 Yes OR 9 .

[0111] R 9 is hydrogen, C1-C 10 Alkyl, C1-C 10 Halogenated alkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C6-C 10 Aryl C1-C3 alkyl, 1 to 4 R 13 The group substituted C6-C 10 Aryl C1-C3 alkyl, heteroaryl C1-C3 alkyl, or 1 to 3 R 13 Preferably, R 9 is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C2 alkoxy C1-C2 alkyl, phenyl C1-C2 alkyl, or 1-2 groups R 13 substituted phenyl C1-C2 alkyl, more preferably hydrogen, C1-C4 alkyl, C1-C2 alkoxy C1-C2 alkyl, or phenyl C1-C2 alkyl, still more preferably hydrogen, C1-C4 alkyl or phenyl C1-C2 alkyl. Even more preferably, R 9 is C1-C4 alkyl. Even more preferably, R 9 It's methyl.

[0112] R10 is hydrogen, C1-C6 alkyl, SO2R 14 Preferably, R 10 Is hydrogen or SO2R 14 , more preferably SO2R 14 .

[0113] R 11 is hydrogen or C1-C6 alkyl. Preferably, R 11 It's hydrogen.

[0114] Or, R 10 and R 11 Together with the nitrogen to which they are attached they form a 3- to 6-membered heterocyclyl ring.

[0115] R 12 is hydrogen, C1-C4 alkyl or C1-C4 alkylcarbonyl. 12 It is hydrogen, C1-C2 alkyl or C1-C2 alkylcarbonyl, more preferably hydrogen or methyl.

[0116] R 13 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano or C1-C4 alkylsulfonyl. 13 It is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano or C1-C4 alkylsulfonyl.

[0117] R 14 is C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkyl (C1-C4 alkyl) amino. 14 It is a C1-C4 alkyl group or a C1-C4 alkyl(C1-C4 alkyl)amino group, and more preferably a methyl group or an isopropyl(methyl)amino group.

[0118] R 15 is hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl. 15 It is hydrogen, halogen or C1-C2 alkyl, more preferably it is hydrogen or methyl, still more preferably it is hydrogen.

[0119] R 16 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano or C1-C4 alkylsulfonyl. 16 is halogen, more preferably fluorine.

[0120] R 17is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 Preferably, R 17 It is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, more preferably hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl, most preferably hydrogen, fluorine, chlorine, methyl or trifluoromethyl.

[0121] R 18 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 Preferably, R 18is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, more preferably hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl, still more preferably hydrogen, fluorine, chlorine, methyl or trifluoromethyl. Even more preferably, R 18 It's hydrogen.

[0122] R 19 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 Preferably, R 19 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, more preferably hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl, still more preferably hydrogen, fluorine, chlorine, methyl, difluoromethyl, trifluoromethyl or 1,1-difluoroethyl. Even more preferably, R 19 It's chlorine.

[0123] R 20 and R 21 are each independently hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C4 alkoxy or -CH2OR 12 Preferably, R 20 and R 21 Each is independently hydrogen, C1-C4 alkyl or C1-C2 alkoxy, more preferably hydrogen or C1-C2 alkyl, still more preferably hydrogen or methyl.

[0124] In which X 1 , X 2 , X 3 and X 4 In embodiments where two of them are nitrogen, preferably X 2 or X3 is nitrogen. 1 , X 2 , X 3 and X 4 In embodiments where one of the X 2 It's nitrogen.

[0125] A subgroup of preferred compounds are the following compounds, among which:

[0126] X 1 Yes CR 1 ;

[0127] X 2 It is nitrogen;

[0128] X 3 Yes CR 18 ;

[0129] X 4 Yes CR 19 ;

[0130] Y is CH;

[0131] B is O or NH;

[0132] m is 0;

[0133] n is 1 or 2;

[0134] R 1 is hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl;

[0135] R 2 is hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl;

[0136] R 3 is hydrogen, chlorine or fluorine;

[0137] R 4 is chlorine, bromine or cyano;

[0138] R 6 and R 7 Each is independently hydrogen, halogen or C1-C2 alkyl;

[0139] R 8 Yes OR 9 ;

[0140] R 9 is hydrogen, C1-C4 alkyl, C1-C2 alkoxy C1-C2 alkyl or phenyl C1-C2 alkyl; R 18 is hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl;

[0141] R 19 It is hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl.

[0142] R 20 and R 21 Each is independently hydrogen or C1-C2 alkyl.

[0143] Another subgroup of preferred compounds are the following compounds, among which:

[0144] X 1 Yes CR 1 ;

[0145] X 2 Yes CR 17 ;

[0146] X 3 It is nitrogen;

[0147] X 4 Yes CR 19 ;

[0148] Y is CH;

[0149] B is O or NH;

[0150] m is 0;

[0151] n is 1 or 2;

[0152] R 1 is hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl;

[0153] R 2 and R 19 Together with the carbon atoms to which they are attached, they form a 5- or 6-membered ring containing one or two heteroatoms selected from nitrogen, oxygen and sulfur, and surrounded by 1 to 4 R 16 The group represented by is substituted;

[0154] R 3 is hydrogen, chlorine or fluorine;

[0155] R 4 is chlorine, bromine or cyano;

[0156] R 6 and R 7 are independently hydrogen, halogen or C1-C2 alkyl;

[0157] R 8 Yes OR 9 ;

[0158] R 9 is hydrogen, C1-C4 alkyl, C1-C2 alkoxy C1-C2 alkyl or phenyl C1-C2 alkyl;

[0159] R 16 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano or C1-C4 alkylsulfonyl;

[0160] R 17 It is hydrogen, fluorine, chlorine, C1-C2 alkyl or C1-C2 haloalkyl.

[0161] R 20 and R 21 Each is independently hydrogen or C1-C2 alkyl.

[0162] A subgroup of more preferred compounds are the following compounds, among which:

[0163] X 1 Yes CR 1 ;

[0164] X 2 It is nitrogen;

[0165] X 3 Yes CR 18 ;

[0166] X 4 Yes CR 19 ;

[0167] Y is CH;

[0168] B is O or NH;

[0169] m is 0;

[0170] n is 2;

[0171] R 1 is hydrogen, fluorine, chlorine, methyl or trifluoromethyl;

[0172] R 2 is hydrogen, fluorine, chlorine, methyl or trifluoromethyl;

[0173] R 3 is hydrogen or fluorine;

[0174] R 4 is chlorine or bromine;

[0175] R 6 and R 7 are each independently hydrogen, chlorine or methyl;

[0176] R 8 Yes OR 9 ;

[0177] R 9is hydrogen, C1-C4 alkyl or phenyl C1-C2 alkyl;

[0178] R 18 is hydrogen, fluorine, chlorine, methyl or trifluoromethyl;

[0179] R 19 is hydrogen, fluorine, chlorine, methyl, difluoromethyl, trifluoromethyl or 1,1-difluoroethyl.

[0180] R 20 and R 21 are each independently hydrogen or methyl.

[0181] Another subgroup of more preferred compounds are the following compounds, among which:

[0182] X 1 Yes CR 1 ;

[0183] X 2 Yes CR 17 ;

[0184] X 3 It is nitrogen;

[0185] X 4 Yes CR 19 ;

[0186] Y is CH;

[0187] B is O or NH;

[0188] m is 0;

[0189] n is 2;

[0190] R 1 is hydrogen, fluorine, chlorine, methyl or trifluoromethyl;

[0191] R 2 and R 19 Together with the carbon atom to which they are attached, they form a saturated 5-membered ring containing one or two oxygen atoms and surrounded by 1 to 3 R 16 The group represented by is substituted;

[0192] R 3 is hydrogen or fluorine;

[0193] R 4 is chlorine or bromine;

[0194] R 6 and R 7 are each independently hydrogen, chlorine or methyl;

[0195] R 8 Yes OR 9 ;

[0196] R 9 is hydrogen, C1-C4 alkyl or phenyl C1-C2 alkyl;

[0197] R 16 It is a halogen;

[0198] R 17 is hydrogen, fluorine, chlorine, methyl or trifluoromethyl; and

[0199] R 20 and R 21 are each independently hydrogen or methyl.

[0200] Another subgroup of even more preferred compounds are the following compounds, among which:

[0201] X 1 Yes CR 1 ;

[0202] X 2 It is nitrogen;

[0203] X 3 Yes CR 18 ;

[0204] X 4 Yes CR 19 ;

[0205] Y is CH;

[0206] B is O or NH;

[0207] m is 0;

[0208] n is 2;

[0209] R 1 It is a halogen;

[0210] R 2 It is hydrogen;

[0211] R 3 It is a halogen;

[0212] R 4 It is a halogen;

[0213] R 6 and R 7 It's all hydrogen;

[0214] R 8 Yes OR 9 ;

[0215] R 9 is a C1-C3 alkyl group;

[0216] R 18It is hydrogen;

[0217] R 19 is a halogen; and

[0218] R 20 and R 21 are each independently hydrogen or methyl.

[0219] A subgroup of particularly preferred compounds are the following compounds, in which: X 1 Yes CR 1 ;

[0220] X 2 It is nitrogen;

[0221] X 3 Yes CR 18 ;

[0222] X 4 Yes CR 19 ;

[0223] Y is CH;

[0224] B is O or NH;

[0225] m is 0;

[0226] n is 2;

[0227] R 1 It is chlorine;

[0228] R 2 It is hydrogen;

[0229] R 3 It is fluorine;

[0230] R 4 It is chlorine;

[0231] R 6 and R 7 It's all hydrogen;

[0232] R 8 Yes OR 9 ;

[0233] R 9 It is methyl;

[0234] R 18 It is hydrogen;

[0235] R 19 is chlorine; and

[0236] R 20 and R 21 are each independently hydrogen or methyl.

[0237] Instance table

[0238] Table 1 below discloses 1140 specific compounds having formula (I), designated as compounds 1-1 to 1-1140, wherein R 3 is hydrogen, R 4 is chlorine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH, and B is oxygen.

[0239] Table 1

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289] *Where X 4 Yes CR 19 , and R 2 and R 19 Together with the carbon atoms to which they are attached, they form a saturated 5-membered ring containing two oxygen atoms and the ring is surrounded by two R 16 The group represented by 16 The groups are all fluorine.

[0290] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is chlorine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 2-1 to 2-1140, respectively.

[0291] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is chlorine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 3-1 to 3-1140, respectively.

[0292] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is bromine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4, R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 4-1 to 4-1140, respectively.

[0293] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is bromine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 5-1 to 5-1140, respectively.

[0294] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is bromine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 6-1 to 6-1140, respectively.

[0295] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is chlorine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 7-1 to 7-1140, respectively.

[0296] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is chlorine, R 20 is hydrogen, R 21is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 8-1 to 8-1140, respectively.

[0297] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is chlorine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 9-1 to 9-1140, respectively.

[0298] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is bromine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) are designated as compound numbers 10-1 to 10-1140, respectively.

[0299] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is bromine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 11-1 to 11-1140, respectively.

[0300] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is bromine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 12-1 to 12-1140, respectively.

[0301] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is chlorine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 13-1 to 13-1140, respectively.

[0302] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is chlorine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 14-1 to 14-1140, respectively.

[0303] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is chlorine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 15-1 to 15-1140, respectively.

[0304] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is bromine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 16-1 to 16-1140, respectively.

[0305] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is bromine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 17-1 to 17-1140, respectively.

[0306] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is bromine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 18-1 to 18-1140, respectively.

[0307] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is chlorine, R 20 is hydrogen, R 21is hydrogen, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 19-1 to 19-1140, respectively.

[0308] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is chlorine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 20-1 to 20-1140, respectively.

[0309] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is chlorine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 21-1 to 21-1140, respectively.

[0310] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is bromine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 22-1 to 22-1140, respectively.

[0311] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is bromine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 23-1 to 23-1140, respectively.

[0312] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is bromine, R 20 is hydrogen, R 21 is hydrogen, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 24-1 to 24-1140, respectively.

[0313] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is chlorine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 25-1 to 25-1140, respectively.

[0314] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is chlorine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 26-1 to 26-1140, respectively.

[0315] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is chlorine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 27-1 to 27-1140, respectively.

[0316] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is bromine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 28-1 to 28-1140, respectively.

[0317] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is bromine, R 20 is hydrogen, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 29-1 to 29-1140, respectively.

[0318] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is bromine, R 20 is hydrogen, R21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 30-1 to 30-1140, respectively.

[0319] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is chlorine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 31-1 to 31-1140, respectively.

[0320] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is chlorine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 32-1 to 32-1140, respectively.

[0321] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is chlorine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 33-1 to 33-1140, respectively.

[0322] 1140 compounds of formula (I) (wherein R 3 is hydrogen, R 4 is bromine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 34-1 to 34-1140, respectively.

[0323] 1140 compounds of formula (I) (wherein R 3 is fluorine, R 4 is bromine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 35-1 to 35-1140, respectively.

[0324] 1140 compounds of formula (I) (wherein R 3 is chlorine, R 4 is bromine, R 20 is methyl, R 21 is methyl, m is 0, Y is CH and B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The values ​​of are as given in Table 1 for compounds 1-1 to 1-1140) were designated as compound numbers 36-1 to 36-1140, respectively.

[0325] The compounds of the present invention can be prepared by techniques known to those skilled in the art of organic chemistry. A general method for producing compounds of formula (I) is described below. Unless otherwise specified herein, the substituent X 1 , X 2 , X 3 , X 4 ,m,Y,B,D,R 1 , R2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 and R 21 is as defined above.

[0326] The starting materials for preparing the compounds of the present invention can be purchased from common commercial suppliers or can be prepared by known methods. The starting materials and intermediates can be purified by methods of the prior art (such as chromatography, crystallization, distillation and filtration) before being used in the next step.

[0327] Compounds of formula (I) can be prepared from compounds of formula (A) and compounds of formula (B) as shown in Reaction Scheme 1.

[0328] Reaction Scheme 1

[0329]

[0330] For example, a mixture of a compound of formula (A) and a compound of formula (B) (wherein Hal represents a halogen atom, such as a chlorine, bromine or iodine atom) can be treated with a metal catalyst (such as palladium acetate) in a suitable solvent (such as dioxane), optionally in the presence of a suitable ligand (such as a phosphine ligand, such as S-Phos) or a preformed complex of the metal and the ligand (such as dppf palladium dichloride) and a base (such as potassium acetate).

[0331] Boronic acids (or the corresponding boric acid esters) of formula (A) are available or can be prepared by methods well known in the literature.

[0332] Compounds of formula (B) can be prepared from anilines of formula (C) as shown in Reaction Scheme 2.

[0333] Reaction Scheme 2

[0334]

[0335] For example, a compound of formula (C) may be treated with a metal halide (such as potassium iodide) and a nitrosating agent (such as sodium nitrite and toluenesulfonic acid) in a suitable solvent (such as a mixture of water and acetonitrile).

[0336] Anilines of formula (C) can be prepared from nitro compounds of formula (D) as shown in Reaction Scheme 3.

[0337] Reaction Scheme 3

[0338]

[0339] For example, a compound of formula (D) may be treated with a reducing agent such as iron and ammonium chloride in a suitable solvent such as a mixture of water and ethanol.

[0340] A nitro compound of formula (D) wherein m is 0 can be prepared from a thiol of formula (E) and a compound of formula (F) wherein LG represents a leaving group, for example a halogen atom, such as a chlorine atom, as shown in Reaction Scheme 4.

[0341] Reaction Scheme 4

[0342]

[0343] For example, a nitro compound of formula (E) may be treated with a compound of formula (F) in the presence of a base such as triethylamine in a suitable solvent such as acetonitrile.

[0344] Nitro compounds of formula (E) are available or can be prepared by methods well known in the literature.

[0345] Compounds of formula (F) can be prepared from alcohols or amines of formula (G) and acids of formula (H) as shown in Reaction Scheme 5.

[0346] Reaction Scheme 5

[0347]

[0348] For example, an acid of formula (H) may be treated with an activating agent such as oxalyl chloride in a suitable solvent such as dichloromethane and dimethylformamide, and the resulting intermediate then treated with an alcohol or amine of formula (G) in the presence of a base such as triethylamine in a suitable solvent such as dichloromethane.

[0349] Alcohols and amines of formula (G) and acids of formula (H) are available or can be prepared by methods well known in the literature.

[0350] Alternatively, a compound of formula (IA), which is a compound of formula (I), wherein m=0, can be prepared from a compound of formula (F) and a thiol of formula (J), as shown in Reaction Scheme 6.

[0351] Reaction Scheme 6

[0352]

[0353] For example, a thiol of formula (J) may be treated with a compound of formula (F) in the presence of a base such as triethylamine in a suitable solvent such as acetonitrile.

[0354] Thiols of formula (J) can be prepared from sulfonyl chlorides of formula (K) as shown in Reaction Scheme 7.

[0355] Reaction Scheme 7

[0356]

[0357] For example, a sulfonyl chloride of formula (K) may be treated with a reducing agent such as tin dichloride in a suitable solvent such as a mixture of water and acetic acid.

[0358] Sulfonyl chlorides of formula (K) can be prepared from compounds of formula (L) as shown in Reaction Scheme 8.

[0359] Reaction Scheme 8

[0360]

[0361] For example, a compound of formula (L) may be treated with a sulfonylating agent such as chlorosulfonic acid.

[0362] Compounds of formula (L) can be prepared from compounds of formula (M) and compounds of formula (A), as shown in Reaction Scheme 9.

[0363] Reaction Scheme 9

[0364]

[0365] For example, a mixture of a compound of formula (A) and a compound of formula (M) (wherein Hal represents a halogen atom, such as a chlorine, bromine or iodine atom) can be treated with a metal catalyst (such as palladium acetate) in a suitable solvent (such as dioxane), optionally in the presence of a suitable ligand (such as a phosphine ligand, such as S-Phos) or a preformed complex of the metal and the ligand (such as dppf palladium dichloride) and a base (such as potassium acetate).

[0366] Boronic acids (or the corresponding boric acid esters) of formula (A) are available or can be prepared by methods well known in the literature.

[0367] Compounds of formula (M) are available or can be prepared from anilines of formula (N) as shown in reaction scheme 10.

[0368] Reaction Scheme 10

[0369]

[0370] For example, a compound of formula (N) may be treated with a metal halide (such as potassium iodide) and a nitrosating agent (such as sodium nitrite and toluenesulfonic acid) in a suitable solvent (such as a mixture of water and acetonitrile).

[0371] Compounds of formula (I) can also be prepared from acids of formula (P) and alcohols or amines of formula (G), as shown in Reaction Scheme 11.

[0372] Reaction Scheme 11

[0373]

[0374] For example, an acid of formula (P) may be treated with an activating agent such as oxalyl chloride in a suitable solvent such as dichloromethane and dimethylformamide, and the resulting intermediate then treated with an alcohol or amine of formula (G) in the presence of a base such as triethylamine in a suitable solvent such as dichloromethane.

[0375] Acids of formula (P) can be prepared from esters of formula (Q) wherein R represents an alkyl group or a similar group, as shown in Reaction Scheme 12.

[0376] Reaction Scheme 12

[0377]

[0378] For example, a compound of formula (Q) may be treated with hydrochloric acid in a suitable solvent such as dioxane.

[0379] Esters of formula (Q) (wherein m is 0) can be prepared from thiols of formula (J) and esters of formula (R) (wherein LG represents a leaving group, e.g., a halogen atom, such as a chlorine atom, and R represents an alkyl group or the like), as shown in Reaction Scheme 13.

[0380] Reaction Scheme 13

[0381]

[0382] For example, a thiol of formula (J) may be treated with a compound of formula (R) in the presence of a base such as triethylamine in a suitable solvent such as acetonitrile.

[0383] Esters of formula (R) are available or can be prepared by methods well known in the literature.

[0384] Compounds of formula (IB) (which is a compound of formula (I) wherein m is 1 or 2) can be prepared from compounds of formula (IA) (which is a compound of formula (I) wherein m is 0) as shown in Reaction Scheme 14.

[0385] Reaction Scheme 14

[0386]

[0387] For example, a compound of formula (IA) may be treated with an oxidising agent such as potassium peroxymonosulfonate (oxone) or m-chloroperbenzoic acid in a suitable solvent such as acetonitrile or dichloromethane.

[0388] It can be made from a compound of formula (ID) (which is a compound of formula (I) wherein R 8 Yes OR 9 ) prepares a compound having formula (IC) (which is a compound having formula (I) wherein R 8 is an OH group), as shown in Reaction Scheme 15.

[0389] Reaction Scheme 15

[0390]

[0391] For example, a compound of formula (ID) may be treated with hydrochloric acid in a suitable solvent such as dioxane.

[0392] A compound of formula (IE) (which is a compound of formula (I) wherein R 8 YesNR 10 R 11 ), as shown in Reaction Scheme 16.

[0393] Reaction Scheme 16

[0394]

[0395] For example, a compound of formula (IC) can be treated with a halogenating agent such as oxalyl chloride in a suitable solvent such as dichloromethane to form an acyl halide, which can be catalyzed by reacting the acyl halide with a reagent HNR in the presence of a base such as triethylamine in a suitable solvent such as dichloromethane. 10 R 11 to be processed.

[0396] Those skilled in the art will recognize that the order in which the above-described transformations are performed can often be changed or combined in an alternative manner to prepare various compounds of formula (I). Multiple steps can also be combined in a single reaction. All such variations are contemplated to be within the scope of the present invention.

[0397] The skilled artisan will also appreciate that some reagents will react with the substituent X as defined herein. 1 , X 2 , X 3 , X 4 ,m,Y,B,D,R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 and R 21 Certain values ​​or combinations of are incompatible, and any additional steps, such as protection and / or deprotection steps, necessary to achieve the desired transformation will be clear to the skilled person.

[0398] The compounds according to the invention can be used as herbicides in unmodified form, but they are usually formulated into compositions in various ways using formulation adjuvants such as carriers, solvents and surface-active substances. These formulations can be in different physical forms, for example in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, flowable oils, aqueous dispersions, oily dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or water-miscible organic solvents as carriers), impregnated polymer films or in other known forms, for example from Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, 1st edition, second revision (2010). For water-soluble compounds, soluble liquids, water-soluble concentrates or water-soluble granules are preferred. Such formulations can be used directly or can be diluted before use. Dilution can be carried out with, for example, water, liquid fertilizers, micronutrients, biological organisms, oils or solvents.

[0399] These formulations can be prepared, for example, by mixing the active ingredient with a formulation adjuvant in order to obtain a composition in the form of a finely divided solid, granules, solution, dispersion or emulsion. The active ingredients can also be formulated with other adjuvants, for example finely divided solids, mineral oils, oils of plant or animal origin, modified oils of plant or animal origin, organic solvents, water, surface-active substances or combinations thereof.

[0400] These active ingredients can also be contained in very fine microcapsules. Microcapsules contain active ingredients in porous carriers. This allows the active ingredients to be released (e.g., slowly released) to the environment in a controlled amount. Microcapsules typically have a diameter of from 0.1 to 500 microns. The amount of active ingredients they contain is about 25% to 95% of the capsule weight by weight. These active ingredients can be in the form of a holistic solid, in the form of fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulated film can include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane or chemically modified polymers and starch xanthate or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed, in which the active ingredients are contained in the form of finely dispersed particles in a solid matrix of a base material, but these microcapsules themselves are not wrapped.

[0401] Formulation adjuvants suitable for preparing the compositions according to the invention are known per se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl Formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, alkyl pyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, acetic acid glyceryl, diacetic acid glyceryl, triacetin, decaglycerol Hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate , propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol and higher molecular weight alcohols such as amyl alcohol, tetrahydrofuranol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0402] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar materials.

[0403] Many surface-active substances can be used advantageously in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier before use. Surface-active substances can be anionic, cationic, nonionic or polymeric and they can act as emulsifying agents, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium dodecylsulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide addition products, such as ethoxylated nonylphenol; alcohol / alkylene oxide addition products, such as ethoxylated tridecanol; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; salts of dialkylsulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitan oleate; quaternary amines, such as dodecyltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphates; and also further substances, such as are described, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Company. Corp., Ridgewood New Jersey (1981).

[0404] Additional adjuvants that can be used in pesticidal formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, substances and buffers that neutralize or change the pH, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, microbicides, and liquid and solid fertilizers.

[0405] The composition according to the invention may include an additive comprising an oil of plant or animal origin, a mineral oil, an alkyl ester of such an oil or a mixture of such an oil with an oil derivative. The amount of the oil additive in the composition according to the invention is generally from 0.01% to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oil or oil of plant origin, such as rapeseed oil, olive oil or sunflower oil; emulsified vegetable oils; alkyl esters of oils of plant origin, such as methyl derivatives; or oils of animal origin, such as fish oil or tallow. Preferred oil additives include C8-C 22 Alkyl esters of fatty acids, especially C 12 -C 18Methyl derivatives of fatty acids, such as the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th edition, Southern Illinois University, 2010.

[0406] The herbicidal composition generally comprises from 0.1% to 99% by weight, especially from 0.1% to 95% by weight of a compound of formula (I) and from 1% to 99.9% by weight of a formulation adjuvant, which preferably includes from 0 to 25% by weight of a surfactant. The composition of the present invention generally comprises from 0.1% to 99% by weight, especially from 0.1% to 95% by weight of a compound of the present invention and from 1% to 99.9% by weight of a formulation adjuvant, which preferably includes from 0 to 25% by weight of a surfactant. While commercial products may preferably be formulated as concentrates, end users will typically use dilute formulations.

[0407] The application rate varies within a wide range and depends on the nature of the soil, the application method, the crop plants, the harmful organisms to be controlled, the prevailing climatic conditions, and other factors governed by the application method, the application time and the target crop. In general, the compound can be applied at a rate of from 1 l / ha to 2000 l / ha, especially from 10 l / ha to 1000 l / ha.

[0408] Preferred formulations may have the following composition (wt%):

[0409] Emulsifiable concentrates :

[0410] Active ingredient: 1% to 95%, preferably 60% to 90%

[0411] Surfactant: 1% to 30%, preferably 5% to 20%

[0412] Liquid carrier: 1% to 80%, preferably 1% to 35%

[0413] Dust Agent :

[0414] Active ingredient: 0.1% to 10%, preferably 0.1% to 5%

[0415] Solid carrier: 99.9% to 90%, preferably 99.9% to 99%

[0416] Suspension concentrate:

[0417] Active ingredient: 5% to 75%, preferably 10% to 50%

[0418] Water: 94% to 24%, preferably 88% to 30%

[0419] Surfactant: 1% to 40%, preferably 2% to 30%

[0420] Wettable powder :

[0421] Active ingredient: 0.5% to 90%, preferably 1% to 80%

[0422] Surfactant: 0.5% to 20%, preferably 1% to 15%

[0423] Solid carrier: 5% to 95%, preferably 15% to 90%

[0424] Granules:

[0425] Active ingredient: 0.1% to 30%, preferably 0.1% to 15%

[0426] Solid carrier: 99.5% to 70%, preferably 97% to 85%

[0427] Compositions of the present invention may further comprise at least one additional pesticide. For example, compounds according to the present invention may also be used in combination with other herbicides or plant growth regulators. In a preferred embodiment, the additional pesticide is a herbicide and / or a herbicide safener.

[0428] Thus, the compounds of formula (I) may be used in combination with one or more other herbicides to provide various herbicidal mixtures. Specific examples of such mixtures include (wherein "I" represents a compound having formula (I)): I+acetochlor; I+ acifluorfen (including acifluorfen-sodium); I+ bensulfuron; I+ alachlor; I+ fenpyroxil; I+ azomethin; I+ chloranil; I+ azomethin; I+ amitriptyline; I+ amidosulfuron; I+ cyproconazole; I+ aminopyralid; I+ cyproconazole; I+ sulfamethoxam; I+ atrazine; I+ benzylsulfuron-methyl (including benzylsulfuron-methyl); I+ thiamethoxam; I+ bicyclopyrone; I+ bialaphos; I+ pyrifos; I+ bispyribac-sodium; I+ bixlozone; I+ bromocriptine; I+ bromoxynil; I+ butachlor; I+ fluazifop-butyl; I+ pyraclostrobin; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil; I+ chloranil I+ chlorpyrifos-butyl (including chlorpyrifos-butyl-ethyl); ester sulfone oxachlor (including ester sulfone oxachlor-methyl); I+ chlorimuron (including chlorimuron-ethyl); I+ chlorotoluron; I+ ethersulfone oxachlor; I+ chlorsulfuron; I+ cyproconazole; I+ clacyfos; I+ clethodim; I+ clodinafop-butyl (including clodinafop-butyl-propargyl); I+ isocyanate; I+ clopyralid; I+ cyclopyranil; I+ cyclopyrimorate; I+ cyprosulfuron; I+ cyhalofop-butyl (including cyhalofop-butyl-butyl); I+ 2,4-D (including its choline salt and 2-ethylhexyl ester); I+ 2,4-DB; I+ herbicides I+ betamethasone; I+ dicamba (including its aluminum, aminopropyl, bis-aminopropyl methyl, choline, dichloropropane, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts); I+ dimethoate; I+ bisclorac; I+ fluazifop; I+ difenac; I+ fluazifop; I+ flufenac; I+ dimethoate; I+ dimethoate; I+ diquat dibromide; I+ diuron; I+ dimethoate; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ fenac; I+ Bispyribac; I+ clofopyralid; I+ fluazifop-butyl (including fluazifop-butyl-butyl); I+ fluoxathiapiprolin (including fluoxathiapiprolin-sodium); I+ flufenacet; I+ flumetrafen; I+ fluazifop-butyl; I+ flufenacet-propenyl; I+ fluazifop-butyl; I+ flufenacet-propenyl; I+ flupyramide (including fluroxypyr-meptyl); I+ fluthiazol-butyl; I+ flufenacet-butyl; I+ foramsulfuron; I+ glufosinate (including its ammonium salt); I+ glyphosate (including its hydrazine, isopropyl ammonium and potassium salt); I+ halauxifen (including halauxifen-methyl); I+ clofosinate-methyl;I+ haloxyfop-butyl (including haloxyfop-methyl); I+ cyclazinone; I+ hydantocidin; I+ methoxyfenpyr; I+ methylfenpyr; I+ imazapyr; I+ imazapyr; I+ imazapyr; I+ indaziflam; I+ iodosulfuron-methyl (including iodosulfuron-methyl-sodium); I+ iofensulfuron; I+ iofensulfuron-sodium; I+ iobenzonitrile; I+ ipfencarbazone; I+ isoproturon; I+ isoxaben; I+ isoxaflutole; I+ lactofenpyr; I+ lancotrione; I+ linuron ; I+MCPA; I+MCPB; I+mecoprop-P; I+mefenacet; I+methyl disulfone; I+methyl disulfone-methyl; I+mesotrione; I+metamethoxazole; I+metachlor; I+methiozolin; I+methiozolin; I+isopropylamine; I+sulfuron; I+sulfuron; I+methoxazolidinone; I+methoxysulfuron; I+methoxysulfuron; I+methoxysulfuron; I+methosulfuron; I+methosulfuron; I+methozolin; I+fenacet ... I+piperidin; I+piperidin; I+pretilachlor; I+flumisulfuron-methyl; I+aminofluralin; I+promethazine; I+pyrimidin; I+pyrimidin; I+pyroxasulfone; I+pyroxasulfone; I+pyrimidin; I+quinazolin; I+propyrisulfuron, I+propyrisulfuron; I+bencarb; I+flumisulfuron; I+bifenazolin; I+pyrazosulfuron; I+pyrazosulfuron-ethyl; I+pyrazosulfuron; I+pyrimidin; I+pyrrolidin ... =Zothiocarb (including quizalofop-ethyl and quizalofop-P-tefuryl); I+sulfonesulfuron; I+bensulfuron; I+sethoxydim; I+simazine; I+S-isopropylamine; I+sulfuron; I+sulfuron; I+sulfuron; I+sulfuron; I+terbuthiuron; I+tefurin; I+tefurtrione; I+trimethylenesulfuron; I+tefurtrione; I+trimethylenesulfuron; I+terbuthiuron; I+trimethylenesulfuron; I+trimethylenesulfuron; I+tiafenacil; I+tolpyralate; I+benpyraclostrobin; I+triafamone; I+triafamone; I+wild wheat; I+bensulfuron;I+bensulfuron-methyl (including bensulfuron-methyl); I+triclopyr; I+trifloxysulfuron (including trifloxysulfuron-sodium); I+trifludimoxazine; I+fluralin; I+flufenazone; I+trifloxysulfuron; I+4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridinyl]imidazolidin-2-one; I+4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridinyl]imidazolidin-2-one; I+5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridinyl]imidazolidin-2-one; I+4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridinyl]imidazolidin-2-one I+4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one; I+(4R)1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one; I+3-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4 -carbonyl]cyclohexane-1,3-dione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione; I+6-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-ethyl-cyclohexane-1,3-dione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-4,4,6,6-tetramethyl-cyclohexane -1,3-dione; I+2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione; I+3-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione; I+2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione; I+6-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione;I+2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione; I+4-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione and I+4-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione. ;

[0429] Mixtures of compounds of formula (I) may also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, Fourteenth Edition, British Crop Protection Council, 2006.

[0430] The compounds of formula (I) can also be used in a mixture with other agrochemicals such as fungicides, nematicides or insecticides, examples of which are given in the Pesticide Handbook.

[0431] The mixing ratio of the compound of formula (I) to the mixing partner is preferably from 1:100 to 1000:1.

[0432] These mixtures can advantageously be used in the formulations mentioned above ("active ingredient" in this case relates to the corresponding mixture of the compound of formula (I) with the mixing partner).

[0433] The compound of formula (I) of the present invention can also be combined with a herbicide safener. Preferred combinations (where "I" represents a compound of formula (I)) include: -I + fenthiocarb, I + fenthiocarb (including fenthiocarb); I + cyclopropylsulfonamide; I + dichloropropene; I + fenthiocarb (including fenthiocarb ethyl); I + fenthiocarb; I + fluazifop; I + fenthiocarb, I + isoxadiazole (including isoxadiazole ethyl); I + pyrazoline oxadiazole (including pyrazoline oxadiazole); I + metcamifen; I + N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide and I + fenthiocarb.

[0434] Particularly preferred are mixtures of a compound of formula (I) with ciprosulfonamide, isoxadiazole (including isoxadiazole ethyl), cloquintocet-mexyl (including cloquintocet) and / or N-(2-methoxybenzoyl)-4-[(methyl-aminocarbonyl)amino]benzenesulfonamide.

[0435] These safeners of compounds of formula (I) may also be in the form of esters or salts, for example as mentioned in the Handbook of Pesticides (14th edition (BCPC), 2006). References to fenthioquinol also apply to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts (as disclosed in WO 02 / 34048), and references to fenthiocarb ethyl also apply to fenthiocarb, etc.

[0436] 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.

[0437] 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) and the safener).

[0438] The compounds of formula (I) of the present invention are useful as herbicides. Therefore, the present invention further includes a method for controlling unwanted plants, comprising applying an effective amount of a compound of the present invention or a herbicidal composition containing the compound to the plant or a location containing them. 'Control' means killing, reducing or delaying growth or preventing or reducing germination. Usually the plants to be controlled are unwanted plants (weeds). 'Location' means an area where a plant is growing or will grow.

[0439] The application rate of the compound with formula (I) can change within wide limits and depends on the nature of the soil, the method of application (before emergence; after emergence; applied to seed furrows; no-till application, etc.), crop plants, one or more weeds to be controlled, climatic conditions at the time and other factors dominated by the method of application, application time and target crop. The compound with formula (I) according to the present invention is usually applied at a rate from 10g / ha to 2000g / ha, especially from 50g / ha to 1000g / ha. The preferred range is 10-200g / ha.

[0440] Application is usually carried out by spraying the composition, typically by means of a tractor-mounted sprayer for large areas, but other methods such as dusting (for powders), dripping or drenching may also be used.

[0441] Useful plants in which the compositions according to the invention can be used include crops such as cereals, for example barley and wheat, cotton, oilseed rape, sunflower, corn, rice, soybeans, sugar beet, sugar cane and turf.

[0442] Crop plants may also include trees, such as fruit trees, palm trees, coconut trees or other nuts. Also included are vines (such as grapes), shrub fruit trees, fruit plants and vegetables.

[0443] Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-inhibitors, GS-inhibitors, EPSPS-inhibitors, PPO-inhibitors, ACCase-inhibitors and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering. Examples of crops which have been rendered tolerant to imidazolinones (e.g. imazamox) by conventional methods of breeding are Summer rapeseed (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include, for example, maize varieties resistant to glyphosate and glufosinate, which are now and It is commercially available under the trademark ANTIQUID®.

[0444] The compounds of the invention can be used in a method of controlling undesirable vegetation in crop plants that are tolerant to protoporphyrinogen oxidase (PPO) inhibitors. Such plants can be obtained, for example, by transforming crop plants with nucleic acids encoding suitable protoporphyrinogen oxidases, which nucleic acids may contain mutations to render them more resistant to PPO inhibitors. Examples of such nucleic acids and crop plants are disclosed in WO 95 / 34659, WO 97 / 32011, WO 2007 / 024739, WO 2012 / 080975, WO 2013 / 189984, WO 2015 / 022636, WO 2015 / 022640, WO 2015 / 092706、WO 2016 / 099153、WO 2017 / 023778、WO 2017 / 039969、WO 2017 / 217793、WO 2017 / 217794、WO 2018 / 114759、WO 2019 / 117578、WO 2019 / 117579 and WO 2019 / 118726.

[0445] Therefore, the present invention also provides a method for controlling unwanted vegetation in a plant cultivation site, the method comprising the steps of: a) providing a plant comprising at least one nucleic acid comprising a nucleotide sequence encoding a protoporphyrinogen oxidase (PPO) polypeptide at said site, which polypeptide is resistant or tolerant to a "PPO-inhibiting herbicide"; b) applying an effective amount of said herbicide to said site, wherein the PPO-inhibiting herbicide is a compound of formula (I) as defined herein.

[0446] Crops are also to be understood as those crops which have been rendered resistant to harmful insects by genetic engineering methods, such as Bt maize (resistant to the European corn borer), Bt cotton (resistant to the boll weevil) and also Bt potato (resistant to the Colorado beetle). Examples of Bt maize are Bt 176 corn hybrid (Syngenta Seeds). Bt toxins are proteins naturally produced by the soil bacterium Bacillus thuringiensis. Examples of toxins or transgenic plants capable of synthesizing such toxins are described in EP-A-451 878, EP-A-374 753, WO 93 / 07278, WO 95 / 34656, WO 03 / 052073 and EP-A-427 529. Examples of transgenic plants comprising one or more genes encoding insecticide resistance and expressing one or more toxins are (Corn), Yield (corn), (cotton), (cotton), (potato), and Plant crops or their seed material can both be resistant to herbicides and at the same time resistant to insect feeding ("stacked" transgenic results). For example, seeds can have the ability to express insecticidal Cry3 proteins while being tolerant to glyphosate.

[0447] Crops are also to be understood as including those crops which have been obtained by conventional breeding methods or genetic engineering and contain so-called output traits, such as improved storage stability, higher nutritional value and improved flavour.

[0448] Other useful plants include turf grasses such as those grown commercially for lawns on golf courses, lawns, parks and roadsides, and ornamental plants such as flowers or shrubs.

[0449] The compounds and compositions of formula (I) of the present invention can be used to control a variety of monocotyledonous and dicotyledonous weed species in general. Examples of monocotyledonous species that can be typically controlled include Alopecurus myosuroides, Avena fatua, Brachiaria plantaginea, Bromus tectorum, Cyperus esculentus, Digitaria sanguinalis, Echinochloa crus-galli, Lolium perenn, Lolium multiflorum, Panicum miliaceum, Poa annua, Setaria viridis, Setaria faberi, and Sorghum bicolor. Examples of dicotyledonous species that can be controlled include: Abutilon, Amaranthus retroflexus, Bidens pilosa, Chenopodium album, Gorilla indica, Glechoma longituba, Kochia scoparia, Polygonum convolvulus, Echinops thornii, Xinjiang wild rape, Solanum nigrum, Chickweed, Veronica persica and Xanthium sibiricum.

[0450] Unwanted plants are to be understood as also including those weeds which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-inhibitors, GS-inhibitors, EPSPS-inhibitors, PPO-inhibitors, ACCase-inhibitors and HPPD-inhibitors) by evolution, by conventional breeding methods or by genetic engineering. Examples include Palmer amaranth (Amaranthus palmeri) which has evolved resistance to glyphosate and / or acetolactate synthase (ALS)-inhibiting herbicides.

[0451] The compounds of the invention can be used in methods of controlling unwanted plants or weeds that are resistant to protoporphyrinogen oxidase (PPO) inhibitors. For example, Palmer amaranth and Amaranthus sclerosus populations have evolved to be resistant to PPO weeds due to amino acid substitutions in PPX2L, such as substitutions occurring at amino acids R128 (also known as R98) and G399, or deletions of the codon (glycine) at codon 210 (Δ210) in PPX2L, the codon numbering being based on the NCBI reference sequence DQ386114. The compounds of the invention can be used in methods of controlling Palmer amaranth and / or Amaranthus sclerosus having mutations or deletions at the aforementioned codons or equivalents, and it is evident that attempts to use these compounds to control unwanted plants or weeds having other mutations that may occur that confer tolerance or resistance to PPO inhibitors.

[0452] The compounds of formula (I) can also be used for pre-harvest drying of crops, such as, but not limited to, potatoes, soybeans, sunflowers and cotton. Pre-harvest drying is used to dry the leaves of crops without causing significant damage to the crops themselves to aid harvesting.

[0453] The compounds / compositions of the present invention are particularly useful in non-selective burn-down applications and therefore may also be used to control volunteer or escape crop plants.

[0454] Various aspects and embodiments of the invention will now be described in more detail by way of example. It will be appreciated that modifications of detail may be made without departing from the scope of the invention.

[0455] Examples

[0456] The following examples are intended to illustrate but not to limit the present invention.

[0457] Synthesis Example

[0458] Example 1: Preparation of (3-methoxy-3-oxo-propyl) 2-[2-chloro-5-(3,5-dichloro-2-pyridinyl)-4-fluoro-phenyl]sulfanyl propionate (Compound 8-374)

[0459] Step 1: Synthesis of 3,5-dichloro-2-(4-chloro-2-fluoro-phenyl)pyridine

[0460]

[0461] Palladium dichloride (dppf) (1.5 g, 1.8 mmol) is added to a stirred mixture of (4-chloro-2-fluoro-phenyl)-boric acid (3.2 g, 18 mmol), 2-bromo-3,5-dichloro-pyridine (4.0 g, 18 mmol), cesium carbonate (17.4 g, 53 mmol), water (12 ml) and toluene (60 ml). The resulting mixture is heated at 100 °C for 2 hours, then allowed to cool and ethyl acetate (70 ml) and water (20 ml) are added. The phases are separated and the aqueous phase is extracted with ethyl acetate (60 ml). The combined organic phases are dried over sodium sulfate, filtered and evaporated under reduced pressure to leave a residue that is purified by column chromatography to provide 3,5-dichloro-2-(4-chloro-2-fluoro-phenyl)pyridine (4.1 g) as a solid. 1 H NMR (400MHz, CDCl3) δ8.6(d,1H),7.85(d,1H),7.4(t,1H),7.25(dd,1H),7.2(dd,1H)ppm.

[0462] Step 2: Synthesis of 2-chloro-5-(3,5-dichloro-2-pyridyl)-4-fluoro-benzenesulfonyl chloride

[0463]

[0464] Chlorosulfonic acid (1.8 ml, 27 mmol) was added to 3,5-dichloro-2-(4-chloro-2-fluoro-phenyl)pyridine (1.5 g, 5.4 mmol) and the resulting mixture was heated to 140° C. for 3 hours. The mixture was cooled and then added to ice water and the resulting mixture was extracted with added ethyl acetate (2×80 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated under reduced pressure to provide 2-chloro-5-(3,5-dichloro-2-pyridyl)-4-fluoro-benzenesulfonyl chloride (1.8 g) as a solid. 1 HNMR (400MHz, CDCl3) δ8.6(d,1H),8.3(d,1H),7.9(d,1H),7.5(d,1H)ppm.

[0465] Step 3: Synthesis of 2-chloro-5-(3,5-dichloro-2-pyridyl)-4-fluoro-thiophenol

[0466]

[0467] Triphenylphosphine (4.0 g, 15 mmol) was added in portions to a stirred solution of 2-chloro-5-(3,5-dichloro-2-pyridyl)-4-fluoro-benzenesulfonyl chloride (1.8 g, 4.3 mmol) in tetrahydrofuran (22 ml) at room temperature. Water (3.6 ml) was added and the resulting mixture was stirred at ambient temperature for 18 hours. Water (40 ml) and ethyl acetate (90 ml) were added and the phases were separated. The aqueous phase was extracted with ethyl acetate (50 ml) and the combined organic phases were dried over sodium sulfate, filtered and evaporated under reduced pressure to leave a residue which was purified by column chromatography to provide 2-chloro-5-(3,5-dichloro-2-pyridyl)-4-fluoro-thiophenol (1.75 g) as a gum. 1 HNMR (400MHz, CDCl3) δ8.55(d,1H),7.85(d,1H),7.45(d,1H),7.35(d,1H),3.9(s,1H)ppm.

[0468] Step 4: Synthesis of (3-methoxy-3-oxo-propyl) 2-[2-chloro-5-(3,5-dichloro-2-pyridinyl)-4-fluoro-phenyl]sulfanyl propionate (Compound 8-374)

[0469]

[0470] (3-Methoxy-3-oxo-propyl) 2-bromopropanoate (prepared as described in Example 2; 130 mg, 0.53 mmol) was added to a stirred mixture of 2-chloro-5-(3,5-dichloro-2-pyridinyl)-4-fluoro-thiophenol (200 mg, 0.49 mmol), cesium carbonate (160 mg, 0.50 mmol) and acetonitrile (14 ml), and the resulting mixture was stirred at ambient temperature for 2 hours. Ethyl acetate (50 ml) was added, and the resulting mixture was washed with water (2×20 ml), dried over sodium sulfate, filtered and evaporated to leave a residue that was purified by column chromatography to provide (3-methoxy-3-oxo-propyl) 2-[2-chloro-5-(3,5-dichloro-2-pyridinyl)-4-fluoro-phenyl]sulfanyl propanoate (Compound 8-374) (44 mg) as an oil. 1 HNMR (400MHz, CDCl3) δ8.6(d,1H),7.9(d,1H),7.7(d,1H),7.35(d,1H),4.35(m,2H),3.9(q,1H),3.7(s,3H),2.6(m,2H),1.55(d,3H)ppm.

[0471] Example 2: Preparation of (3-methoxy-3-oxo-propyl) 2-bromopropionate

[0472]

[0473] Triethylamine (1.3 ml, 9.1 mmol) and methyl 3-hydroxypropionate (0.48 ml, 5.0 mmol) are added dropwise to a stirred solution of 2-bromopropionyl bromide (0.49 ml, 4.5 mmol) in acetonitrile (15 ml) at 0 ° C. The resulting mixture is stirred at 0 ° C for 1 hour and then at ambient temperature for 2 hours. Water (20 ml) and ethyl acetate (60 ml) are added, the phases are separated, and the aqueous phase is extracted with ethyl acetate (60 ml). The combined organic phases are dried over sodium sulfate, filtered and evaporated under reduced pressure to leave an oil that is purified by column chromatography to provide (3-methoxy-3-oxo-propyl) 2-bromopropanoate (440 mg) as an oil. 1 H NMR (400MHz, CDCl3) δ4.45(m,2H),4.35(m,1H),3.75(s,3H),2.7(t,2H),1.8(d,3H)ppm.

[0474] Example 3: Preparation of 3-[2-[2-chloro-5-(3,5-dichloro-2-pyridinyl)-4-fluoro-phenyl]sulfanylpropionylamino]propionic acid methyl ester (Compound 26-374)

[0475] Step 1: Synthesis of methyl 3-(2-bromopropionylamino)propionate

[0476]

[0477] Triethylamine (2.6 ml, 9.1 mmol) and 2-bromopropionyl bromide (0.97 ml, 9.1 mmol) are added to a stirred mixture of (3-methoxy-3-oxo-propyl)ammonium chloride (1.42 g, 10 mmol) in acetonitrile (30 ml) at 0°C. The resulting mixture is stirred at 0°C for 1 hour and then at ambient temperature for 2 hours. Water (20 ml) and ethyl acetate (60 ml) are added, the phases are separated, and the aqueous phase is extracted with ethyl acetate (60 ml). The combined organic phases are dried over sodium sulfate, filtered and evaporated under reduced pressure to leave an oil that is purified by column chromatography to provide methyl 3-(2-bromopropionylamino)propanoate (560 mg) as a solid. 1 H NMR (400MHz, CDCl3) δ6.95(br s,1H),4.4(q,1H),3.75(s,3H),3.55(m,2H),2.6(m,2H),1.85(d,3H)ppm.

[0478] Step 2: Synthesis of 3-[2-[2-chloro-5-(3,5-dichloro-2-pyridinyl)-4-fluoro-phenyl]sulfanylpropionylamino]propionic acid methyl ester (Compound 26-374)

[0479]

[0480] Methyl 3-(2-bromopropionylamino)propanoate (130 mg, 0.53 mmol) was added to a stirred mixture of 2-chloro-5-(3,5-dichloro-2-pyridinyl)-4-fluoro-thiophenol (prepared as described in Example 1, Step 3; 200 mg, 0.49 mmol), cesium carbonate (160 mg, 0.50 mmol) and acetonitrile (4 ml), and the resulting mixture was stirred at ambient temperature for 1 hour. Ethyl acetate (50 ml) was added, and the resulting mixture was washed with water (2×20 ml), dried over sodium sulfate, filtered and evaporated to leave a residue that was purified by column chromatography to provide methyl 3-[2-[2-chloro-5-(3,5-dichloro-2-pyridinyl)-4-fluoro-phenyl]sulfanylpropionylamino]propanoate (compound 26-374) (36 mg). 1H NMR (400MHz, CDCl3) δ8.55(d,1H),7.85(d,1H),7.45(d,1H),7.3(d,1H),7.05(br t,1H),3.85(q,1H),3.6(s,3H),3.5(m,1H),3.45(m,1H),2.45(t,2H),1.55(d,3H)ppm.

[0481] Preparation Examples

[0482]

[0483] The active ingredient is mixed thoroughly with the adjuvant and the mixture is ground thoroughly in a suitable grinder to provide a wettable powder which can be diluted with water to give a suspension of the desired concentration.

[0484]

[0485] 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.

[0486] Emulsifiable concentrates

[0487]

[0488] Emulsions of any desired dilution which can be used in plant protection can be obtained from these concentrates by dilution with water.

[0489]

[0490] Ready-to-use dusts are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. Such dusts can also be used for dry seed dressing of seeds.

[0491] Extruder Granules

[0492]

[0493] The active ingredient is mixed with the auxiliary and ground, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0494] Coated granules

[0495] Active ingredient [compound of formula (I)] 8%

[0496] Polyethylene glycol (molecular weight 200) 3%

[0497] Kaolin 89%

[0498] 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.

[0499] Suspension concentrates

[0500]

[0501] The finely ground active ingredients are intimately mixed with adjuvants to give suspension concentrates from which suspension concentrates of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants together with plant propagation materials can be treated and protected against infection by microorganisms by spraying, pouring or immersion.

[0502] Flowable concentrate for seed treatment

[0503]

[0504] The finely ground active ingredients are intimately mixed with adjuvants to give suspension concentrates from which suspension concentrates of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants together with plant propagation materials can be treated and protected against infection by microorganisms by spraying, pouring or immersion.

[0505] Extended-release capsule suspension

[0506] 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, 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water are added. The mixture is stirred until the polymerization reaction is complete. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% of active ingredient. The diameter of the medium capsule is 8-15 microns. The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for this purpose.

[0507] Biological Examples

[0508] Pre-emergence biological efficacy

[0509] Seeds of weeds and / or crops were sown in standard soil in pots (Amaranthus palmeri (AMAPA), Lolium perenne (LOLPE), Euphorbia heterophylla (EPHHL), Ipomoea hederacea (IPOHE), Setaria faberi (SETFA), Echinochloa crus-galli (ECCHCG)). After one day of cultivation under controlled conditions in the greenhouse (at 24°C / 19°C, day / night; 16 h light), the plants were sprayed with an aqueous spray solution obtained as follows: the industrial active ingredient was formulated in a small amount of acetone and a special solvent and emulsifier mixture called IF50 (11.12% Emulsogen EL360 TM + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether) to produce a 50 g / l solution, which was then diluted using 0.2% Genapol XO80 as diluent to give the desired final dose of the test compound.

[0510] These test plants were then grown under controlled conditions in a greenhouse (at 24°C / 18°C, day / night; 15 hours of light; 50% humidity) and watered twice a day. After 13 days, the test was evaluated (100 = complete damage to the plant; 0 = no plant damage). The results are shown in Table 2 below.

[0511] Table 2

[0512]

[0513] Biological efficacy after emergence

[0514] Seeds of weeds and / or crops were sown in standard soil in pots (AMAPA, CHEAL, EPHHL, IPOHE, ELEUSINEINDICA, LOLPE, DIGSA, SETFA, ECHCG). After 14 days of cultivation under controlled conditions in the greenhouse (at 24°C / 19°C, day / night; 16 h light), the plants were sprayed with an aqueous spray solution obtained as follows: the technical active ingredient was formulated in a small amount of acetone and a special solvent and emulsifier mixture called IF50 (11.12% Emulsogen EL360 TM + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether) to produce a 50 g / l solution, which was then diluted using 0.2% Genapol XO80 as diluent to give the desired final dose of the test compound.

[0515] These test plants were then grown under controlled conditions in a greenhouse (at 24°C / 18°C, day / night; 15 hours of light; 50% humidity) and watered twice a day. After 13 days, the test was evaluated (100 = complete damage to the plant; 0 = no plant damage). The results are shown in Table 3 below.

[0516] Table 3

[0517]

Claims

1. A compound of formula (I) or an agronomically acceptable salt thereof: X 1 Yes CR 1 , nitrogen or N + -O - ; X 2 Yes CR 17 or nitrogen; X 3 Yes CR 18 or nitrogen; X 4 Yes CR 19 or nitrogen; The premise is X 1 , X 2 , X 3 and X 4 At most two of them are nitrogen, and X 3 and X 4 Both are not nitrogen; Y is CH or nitrogen; B is O, S or NR 5 ; D is -[C(R 6 )(R 7 )] n -; m is an integer from 0 to 2; n is an integer from 1 to 4; R 1 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 ; R 2 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl acyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, CO2R 9 or CONR 10 R 11 ;or R 1 and R 2 Together with the carbon atom to which they are attached, they form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and may optionally contain one or two heteroatoms selected from nitrogen, oxygen and sulfur and may be replaced by 1 to 4 residues consisting of R 16 or R 2 and R 19 Together with the carbon atom to which they are attached, they form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and may optionally contain one or two heteroatoms selected from nitrogen, oxygen and sulfur and may be replaced by 1 to 4 residues consisting of R 16 The group represented by is substituted; R 3 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio or C1-C4 alkylsulfonyl; R 4 is hydrogen, halogen, cyano, nitro, aminocarbonyl, aminothiocarbonyl, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkylsulfonyl; R 5 is hydrogen, hydroxy, C1-C6 alkyl or C1-C4 alkoxy; R 6 and R 7 are each independently hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, hydroxy, C1-C4 alkoxy, C1-C4 alkoxycarbonyl or -CH2OR 12 ; The premise is R 6 and R 7 Not all hydroxyl groups are on the same carbon atom; Alternatively, two R on the same carbon atom or on different carbon atoms 6 and R 7 The groups together form a C1-C5 alkylene chain containing 0, 1 or 2 oxygen atoms, separated by 1 to 3 R 15 The group represented by is substituted; Alternatively, two R 6 and R 7 The groups together form C2-C3 alkenes; R 8 Yes OR 9 , SR 9 or NR 10 R 11 ; R 9 is hydrogen, C1-C 10 Alkyl, C1-C 10 Halogenated alkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C6-C 10 Aryl C1-C3 alkyl, 1 to 4 R 13 The group substituted C6-C 10 Aryl C1-C3 alkyl, heteroaryl C1-C3 alkyl, or 1 to 3 R 13 A group representing a substituted heteroaryl C1-C3 alkyl group; R 10 is hydrogen, C1-C6 alkyl, SO2R 14 ; R 11 is hydrogen or C1-C6 alkyl; or R 10 and R 11 together with the nitrogen to which they are attached, form a 3- to 6-membered heterocyclyl ring; R 12 is hydrogen, C1-C4 alkyl or C1-C4 alkylcarbonyl; R 13 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano or C1-C4 alkylsulfonyl; R 14 is C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkyl(C1-C4 alkyl)amino; R 15 is hydrogen, halogen, C1-C4 alkyl or C1-C4 haloalkyl; R 16 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano or C1-C4 alkylsulfonyl; R 17 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 ; R 18 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 ; R 19 is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy C1-C6 alkyl, C1-C4 haloalkoxy C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl alkyl, C1-C4 haloalkylthio, C1-C4 haloalkylsulfinyl, C1-C4 haloalkylsulfonyl, amino, C1-C4 alkylamino, di(C1-C4 alkyl)amino, C1-C4 alkylcarbonylamino, C1-C4 alkylcarbonyl(C1-C4 alkyl)amino, C1-C4 alkoxycarbonylamino, aminocarbonylamino, C1-C4 alkylaminocarbonylamino, C1-C4 alkylsulfonylamino, C1-C4 haloalkylsulfonylamino, -CO2R 9 or-CONR 10 R 11 ; R 20 and R 21 are each independently hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C4 alkoxy or -CH2OR 12 ; Or two R 20 and R 21 The groups together with the carbon atoms to which they are attached form a C2-C5 alkylene chain, wherein the C2-C5 alkylene chain contains 0, 1 or 2 oxygen atoms, and wherein the C2-C5 alkylene chain is substituted by 1 to 3 R 15 The group represented by is substituted; Or two R 20 and R 21 The groups, together with the carbon atom to which they are attached, form a C2-C3 alkene; and The premise is R 1 , R 2 , R 17 , R 18 and R 19 Not all hydrogen.

2. The compound according to claim 1, wherein X 1 Yes CR 1 .

3. The compound according to claim 1 or claim 2, wherein X 2 It's nitrogen.

4. A compound as claimed in any preceding claim, wherein X 3 Yes CR 18 .

5. A compound as claimed in any preceding claim, wherein X 4 Yes CR 19 .

6. A compound as claimed in any preceding claim, wherein Y is CH.

7. A compound as claimed in any preceding claim, wherein B is O, NH and NCH3.

8. A compound as claimed in any preceding claim, wherein n is 2.

9. A compound as claimed in any preceding claim, wherein R 2 is hydrogen, fluorine, chlorine, methyl or trifluoromethyl.

10. A compound as claimed in any preceding claim, wherein R 3 It is hydrogen, chlorine or fluorine.

11. A compound as claimed in any preceding claim, wherein R 4 It is hydrogen, chlorine, bromine, cyano or aminothiocarbonyl, preferably chlorine, bromine or cyano.

12. A compound as claimed in any preceding claim, wherein R 8 is OR 9 。 13. An agrochemical composition comprising a herbicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 12, and an agrochemically acceptable diluent or carrier.

14. A method of controlling or preventing unwanted vegetation, wherein a herbicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 12, or a composition as claimed in claim 13, is applied to the plants, parts thereof or the locus thereof.

15. A method for controlling undesirable vegetation in a plant cultivation location, the method comprising the steps of: a) providing at said locus a plant comprising at least one nucleic acid comprising a nucleotide sequence encoding a protoporphyrinogen oxidase (PPO) polypeptide, said polypeptide being resistant or tolerant to a "PPO-inhibiting herbicide"; b) applying to said locus an effective amount of said herbicide, wherein said PPO-inhibiting herbicide is a compound as claimed in any preceding claim.

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