Herbicidal compounds

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1, useful as pesticides, especially as herbicides. TIFF2025507086000055.tif53154

Description

[Technical field]

[0001] The present invention relates to herbicidally active compounds and to processes and intermediates used in the preparation of such derivatives. The invention further extends to herbicidal compositions containing such derivatives and the use of such compounds and compositions for the control of undesirable plant growth, particularly for the control of weeds in crops of useful plants. [Background technology]

[0002] WO 2002 / 42275 and US Pat. No. 6,010,980 both disclose herbicidally active 2-substituted pyridine compounds. Summary of the Invention [Means for solving the problem]

[0003] The present invention is based on the finding that compounds of formula (I) as defined herein exhibit surprisingly good herbicidal activity. Thus, according to the present invention, a compound of formula (I): [ka] (In the formula, X 1 CR 1 , nitrogen and N + -O - Selected from; X 2 CR 17 and nitrogen; X 3 CR 18 and nitrogen; X 4 CR 19 and nitrogen; However, X 1 , X 2 , X 3 and X 4 At most two of the X are nitrogen. 3 and X 4 provided that neither of the is nitrogen; Y is selected from CH and nitrogen; B is O, S and NR 5 Selected from; D is (CR 6 R 7 ) n and; n is an integer from 1 to 4; R 1 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkyl sulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, Amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 Alkyl)amino, C1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, Aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkyl sulfonyl amino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 Selected from; R 2 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkyl sulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, Amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, Aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkyl sulfonyl amino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 or R 1 and R 2 together with the carbon atoms to which they are attached form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated, which may optionally contain 1 or 2 heteroatoms selected from nitrogen, oxygen and sulfur; R 16 or R 2 and R 19 together with the carbon atoms to which they are attached form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated, which may optionally contain 1 or 2 heteroatoms selected from nitrogen, oxygen and sulfur; R 16 may be substituted with 1 to 4 groups represented by R 3 is hydrogen, halogen, C 1 ~C4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylthio and C 1 ~C 4 alkylsulfonyl; R 4 is hydrogen, halogen, cyano, nitro, aminocarbonyl, aminothiocarbonyl, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy and C 1 ~C 4 alkylsulfonyl; R 5 is hydrogen, hydroxyl, C 1 ~C 6 Alkyl, and C 1 ~C 4 alkoxy; Each R 6 and R 7 is hydrogen, halogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, Hydroxy, C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkoxycarbonyl, and CH 2 OR 12 are independently selected from; 6 and R 7 are not both hydroxy on the same carbon atom; or two groups R 6 and R 7 on the same or different carbon atoms, together with R 15C, containing 0, 1 or 2 oxygen atoms, substituted by 1 to 3 groups represented by 1 ~C 5 Forming an alkylene chain; or two groups R 6 and R 7 on the same carbon atom, together with the carbon atom to which they are attached, C 2 may form an alkene; R 8 OR 9 , S.R. 9 , and N.R. 10 R 11 Selected from; R 9 is hydrogen, C 1 ~C 10 Alkyl, C 1 ~C 10 Haloalkyl, C 3 ~C 6 Alkenyl, C 3 ~C 6 Haloalkenyl, C 3 ~C 6 Alkynyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 6 ~C 10 Aryl C 1 ~C 3 Alkyl, R 13 C substituted with 1 to 4 groups represented by 6 ~C 10 Aryl C 1 ~C 3 Alkyl, Heteroaryl C 1 ~C 3 Alkyl, and R 13 Heteroaryl C substituted with 1 to 3 groups represented by 1 ~C 3 alkyl; R 10 is hydrogen, C 1 ~C 6Alkyl, and SO 2 R 14 Selected from; R 11 is hydrogen and C 1 ~C 6 alkyl; or R 10 and R 11 together with the nitrogen atom to which they are attached form a 3- to 6-membered heterocyclyl ring, optionally containing an oxygen atom; R 12 is hydrogen, C 1 ~C 4 Alkyl, and C 1 ~C 4 alkylcarbonyl; Each R 13 is a halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, cyano, and C 1 ~C 4 independently selected from alkylsulfonyl; R 14 is C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl and C 1 ~C 4 Alkyl(C 1 ~C 4 alkyl)amino; Each R 15 is hydrogen, halogen, C 1 ~C 4 Alkyl, and C 1 ~C 4 independently selected from haloalkyl; R 16 is a halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C1 ~C 4 Haloalkoxy, cyano, and C 1 ~C 4 alkylsulfonyl; R 17 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkyl sulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, Amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, Aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkyl sulfonyl amino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 Selected from; R 18 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkyl sulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, Amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, Aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkyl sulfonyl amino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 Selected from; R 19 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkyl sulfonyloxy, C 1 ~C4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, Amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, Aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkyl sulfonyl amino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 Selected from; However, R 1 , R 2 , R 17 , R 18 and R 19 (provided that not all are hydrogen) or an agriculturally acceptable salt thereof.

[0004] 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.

[0005] According to a third aspect of the present invention there is provided a method for controlling or preventing undesired plant growth, wherein a herbicidally effective amount of a compound of formula (I) or a composition comprising this compound as an active ingredient is applied to the plant, its part or its habitat.

[0006] According to a fourth aspect of the present invention there is provided the use of a compound of formula (I) as a herbicide.

[0007] According to a fifth aspect of the invention there is provided a process for preparing a compound of formula (I). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.

[0009] As used herein, cyano refers to the group -CN.

[0010] As used herein, hydroxy refers to an --OH group.

[0011] As used herein, nitro refers to -NO 2 means a group.

[0012] As used herein, amino is —NH 2 means a group.

[0013] As used herein, "C 1 ~C 10The term "alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from 1 to 10 carbon atoms, and attached to the remainder of the molecule by a single bond. 1 ~C 6 Alkyl, C 1 ~C 4 Alkyl and C 1 ~C 2 Alkyl should be construed accordingly. 1 ~C 10 Examples of alkyl include, but are not limited to, methyl (Me), ethyl (Et), n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1-dimethylethyl (t-butyl).

[0014] "C 1 ~C 6 An "alkylene" group has the same structure as C, except that such a group is attached to the remainder of the molecule by two single bonds. 1 ~C 6 Refers to the corresponding definition of alkyl. 1 ~C 2 The term "alkylene" should be construed accordingly. 1 ~C 6 Examples of alkylene include, but are not limited to, -CH 2 -, -CH 2 CH 2 - and -(CH 2 ) 3 -- are some examples.

[0015] As used herein, "C 1 ~C 4 The term "alkoxy" generally refers to R a C 1 ~C 4 The alkyl group of the formula -OR a C 1 ~C 3 Alkoxy should be construed accordingly. 1- C 4Examples of alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, and t-butoxy.

[0016] As used herein, "C 1 ~C 10 The term "haloalkyl" refers generally to any C1, C2, or C3 alkyl group as defined above, which is substituted with one or more of the same or different halogen atoms. 1 ~C 10 Refers to an alkyl group. 1 ~C 6 Haloalkyl and C 1 ~C 4 Haloalkyl should be construed accordingly. 1 ~C 10 Examples of haloalkyl include, but are not limited to, chloromethyl, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, and 2,2,2-trifluoroethyl.

[0017] As used herein, "C 2 ~C 6 The term "alkenyl" refers to a straight or branched hydrocarbon chain radical group composed solely of carbon and hydrogen atoms, containing at least one double bond which may be in either the (E) or (Z) configuration, having from 2 to 6 carbon atoms and attached to the remainder of the molecule by a single bond. 3 ~C 6 Alkenyl should be construed accordingly. 2 ~C 6 Examples of alkenyl include, but are not limited to, prop-1-enyl, allyl (prop-2-enyl), and but-1-enyl.

[0018] As used herein, "C 2 ~C 6 The term "haloalkenyl" generally refers to any of the C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C31, C42, C53, C64, C76, C88, C99, C100, C111 2 ~C 6 Refers to the alkenyl group. 3~C 6 Haloalkenyl and C 2 ~C 4 Haloalkenyl should be construed accordingly. 2 ~C 6 Examples of haloalkenyls include, but are not limited to, chloroethylene, fluoroethylene, 1,1-difluoroethylene, 1,1-dichloroethylene, and 1,1,2-trichloroethylene.

[0019] As used herein, "C 2 ~C 6 The term "alkynyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from 2 to 6 carbon atoms, and attached to the rest of the molecule by a single bond. 3 ~C 6 Alkynyl and C 2 ~C 4 Alkynyl should be construed accordingly. 2 ~C 6 Examples of alkynyl include, but are not limited to, prop-1-ynyl, propargyl (prop-2-ynyl), and but-1-ynyl.

[0020] As used herein, "C 1 ~C 4 The term "haloalkoxy" refers to any of the C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C30, C41, C52, C63, C74, C85, C96, C97, C98, C99, C100, C111, C12, C13, C24, C14, C15, C25, C16, C17, C26, C18, C27, C30, C41, C52, C63, C74, C85, C96, C97, C101, C112, C12, C25, C30, C41, C52, C63, C74 1 ~C 4 Refers to an alkoxy group. 1 ~C 3 Haloalkoxy should be construed accordingly. 1 ~C 4 Examples of haloalkoxy include, but are not limited to, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy, and trifluoroethoxy.

[0021] As used herein, "C 1 ~C 4Haloalkoxy C 1 ~C 6 The term "alkyl" generally refers to R b C 1 ~C 4 R is a haloalkyl group and is generally as defined above a C 1 ~C 6 The alkylene group of formula R b -OR a - refers to the group.

[0022] As used herein, "C 1 ~C 4 Alkoxy C 1 ~C 6 The term "alkyl" generally refers to R b C 1 ~C 4 R is an alkyl group and is generally as defined above a C 1 ~C 6 The alkylene group of formula R b -OR a - refers to the group.

[0023] As used herein, "C 1 ~C 4 Alkoxy C 1 ~C 4 The term "alkoxy" generally refers to R b C 1 ~C 4 R is an alkyl group, generally as defined above. a C 1 ~C 4 An alkylene group, formula R b -OR a It refers to the -O- group.

[0024] As used herein, "C 1 ~C 4 The term "alkylthio" generally refers to R a C 1 ~C4 An alkyl group of the formula -SR a Refers to the group.

[0025] As used herein, "C 1 ~C 4 The term "alkylsulfonyl" generally refers to a group in which Ra is C as defined above. 1 ~C 4 The alkyl group of the formula -S(O) 2 R a "C" refers to the group 1 ~C 3 Alkylsulfonyl" and "C 1 ~C 2 The term "alkylsulfonyl" should be construed accordingly. 1 ~C 4 Examples of alkylsulfonyl include, but are not limited to, methylsulfonyl.

[0026] As used herein, "C 1 ~C 6 The term "alkylcarbonyl" generally refers to R a C 1 ~C 6 An alkyl group of the formula -C(O)R a C 1 ~C 4 Alkylcarbonyl should be construed accordingly.

[0027] As used herein, "C 1 ~C 6 The term "alkoxycarbonyl" generally refers to R a C 1 ~C 6 An alkyl group of the formula -C(O)OR a C 1 ~C 4 Alkoxycarbonyl should be construed accordingly.

[0028] As used herein, "C 1 ~C4 The term "alkylsulfonyloxy" generally refers to R a C 1 ~C 4 An alkyl group of the formula -OS(O) 2 R a "C" refers to the group 1 ~C 3 Alkylsulfonyloxy" and "C 1 ~C 2 The term "alkylsulfonyloxy" should be construed accordingly.

[0029] As used herein, "C 1 ~C 4 The term "haloalkylsulfonyl" generally refers to R a C 1 ~C 4 A haloalkyl group of the formula -S(O) 2 R a Refers to the group.

[0030] As used herein, "C 1 ~C 4 The term "haloalkylsulfonyloxy" generally refers to R a C 1 ~C 4 A haloalkyl group of the formula -OS(O) 2 R a Refers to the group.

[0031] As used herein, "C 1 ~C 6 The term "alkylsulfinyl" generally refers to R a C 1 ~C 6 An alkyl group of the formula -S(O)R a "C" refers to the group 1 ~C 4 Alkylsulfinyl" and "C 1 ~C 3 The term "alkylsulfinyl" should be construed accordingly. 1 ~C6 Examples of alkylsulfinyl include, but are not limited to, methylsulfinyl.

[0032] As used herein, "C 1 ~C 4 The term "haloalkylsulfinyl" generally refers to R as defined above. a C 1 ~C 4 A haloalkyl group of the formula -S(O)R a Refers to the group.

[0033] As used herein, "C 1 ~C 4 The term "haloalkylthio" generally refers to R, as defined above. a C 1 ~C 4 A haloalkyl group of the formula -SR a Refers to the group.

[0034] As used herein, "C 1 ~C 4 The term "alkylamino" generally refers to R a C 1 ~C 4 An alkyl group of the formula -NHR a Refers to the group.

[0035] As used herein, “N,N-di(C 1 ~C 4 The term "amino" generally refers to R a and R b Each of them is C 1 ~C 4 The alkyl group of the formula -N(R a )(R b ) group. 1 ~C 3 The term "alkyl)amino" should be construed accordingly.

[0036] As used herein, "C 1 ~C 4 The term "alkylcarbonylamino" generally refers to R a C 1 ~C 4 The alkyl group of the formula -NH(O)CR a Refers to the group.

[0037] As used herein, "C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 The term "amino" generally refers to R a and R b Each of them is C 1 ~C 4 The alkyl group of the formula -NH(R a )(O)CR b Refers to the group.

[0038] As used herein, "C 1 ~C 4 Alkyl(C 1 ~C 4 The term "amino" generally refers to R a and R b Each of them is C 1 ~C 4 The alkyl group of the formula -NH(R a )R b Refers to the group.

[0039] As used herein, "C 1 ~C 4 The term "alkyloxycarbonylamino" generally refers to R a C 1 ~C 4 An alkyl group of the formula -NH(O)COR a Refers to the group.

[0040] As used herein, "C 1 ~C 4The term "alkylaminocarbonylamino" generally refers to R a C 1 ~C 4 The alkyl group of the formula -NH(O)CNHR a Refers to the group.

[0041] As used herein, "C 1 ~C 4 The term "alkylsulfonylamino" generally refers to R a C 1 ~C 4 The alkyl group of formula R a S(O) 2 Refers to the group NH-.

[0042] As used herein, "C 1 ~C 4 The term "haloalkylsulfonylamino" generally refers to R a C 1 ~C 4 A haloalkyl group of formula R a S(O) 2 Refers to the group NH-.

[0043] As used herein, the term "aminocarbonyl" refers to a group of the formula -C(O)NH 2 Refers to the group.

[0044] As used herein, the term "aminocarbonylamino" refers to a group of the formula -NH(O)CNH 2 Refers to the group.

[0045] As used herein, the term "aminothiocarbonyl" refers to a compound of the formula -C(S)NH 2 Refers to the group.

[0046] As used herein, "C 3 ~C 6 The term "cycloalkyl" refers to a stable monocyclic ring radical that is saturated or partially unsaturated and contains 3 to 6 carbon atoms.3 ~C 4 Cycloalkyl should be construed accordingly. 3 ~C 6 Examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0047] As used herein, "C 6 ~C 10 The term "aryl" refers to a 6-10 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, naphthalenyl, or indenyl.

[0048] As used herein, "C 6 ~C 10 Aryl C 1 ~C 3 The term "alkyl" means any of the C 1 ~C 3 It refers to an aryl moiety, generally as defined above, attached to the remainder of the molecule by an alkylene linker.

[0049] As used herein, unless otherwise specified, the term "heteroaryl" refers to a 5- or 6-membered monocyclic aromatic ring containing 1, 2, 3, or 4 heteroatoms independently selected from nitrogen, oxygen, and sulfur. Heteroaryl groups can be bonded to the remainder of the molecule through a carbon atom or a heteroatom. Examples of heteroaryl include furyl, pyrrolyl, imidazolyl, thienyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl.

[0050] As used herein, unless otherwise specified, “heteroaryl C 1 ~C 3 The term "alkyl" means any of the C 1 ~C3 It refers to a heteroaryl ring, generally as defined above, attached to the remainder of the molecule by an alkylene linker.

[0051] As used herein, unless otherwise specified, the term "heterocyclyl" or "heterocyclic" refers to a stable 4-6 membered non-aromatic monocyclic ring group containing one, two, or three heteroatoms independently selected from nitrogen, oxygen, and sulfur. The heterocyclyl group may be attached to the remainder of the molecule through a carbon atom or a heteroatom. Examples of heterocyclyl include, but are not limited to, pyrrolinyl, pyrrolidyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl, piperazinyl, tetrahydropyranyl, dihydroisoxazolyl, dioxolanyl, morpholinyl, or δ-lactamyl.

[0052] As used herein, unless otherwise specified, “heterocyclyl C 1 ~C 3 The term "alkyl" means any of the C 1 ~C 3 It refers to a heterocyclyl ring, generally as defined above, attached to the remainder of the molecule by an alkylene linker.

[0053] The presence of one or more optionally asymmetric carbon atoms in the compounds of formula (I) means that the compounds can occur in chiral isomeric forms, i.e. enantiomeric or diastereomeric forms. Astrogenic isomers can also occur as a result of restricted rotation about a single bond. Formula (I) is intended to include all these possible isomeric forms and mixtures thereof. The present invention includes all these possible isomeric forms and mixtures thereof for the compounds of formula (I). Similarly, formula (I) is intended to include all possible tautomers, if present, including lactam-lactim tautomerism and keto-enol tautomerism. The present invention includes all possible tautomeric forms for the compounds of formula (I). Similarly, disubstituted alkenes, if present, can exist in E or Z form or as a mixture of both in any proportion. The present invention includes all these possible isomeric forms and mixtures thereof for the compounds of formula (I).

[0054] The compounds of formula (I) are typically provided in the form of an agriculturally acceptable salt, a zwitterion, or an agriculturally acceptable salt of a zwitterion. The present invention encompasses all such agriculturally acceptable salts, zwitterions, and mixtures thereof in all proportions.

[0055] Suitable agriculturally 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, benethamine, 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, heptadecylamine, heptylamine, hexadecylamine, hexenyl-2-amine, hexylamine, hexylheptylamine, hexyloctylamine, histidine, indoline, isoamylamine, isobutanolamine, isobutylamine, isopropanolamine, isopropylamine, lysine, Examples of suitable amines include amine, 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, stearylamine, 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, tributylsulfoxonium, triethylsulfonium, triethylsulfoxonium, trimethylsulfonium, trimethylsulfoxonium, tripropylsulfonium and tripropylsulfoxonium.

[0056] The following list includes substituents X related to compounds of formula (I) according to the present invention: 1 , X 2 , X 3 , X 4 , Y, B, D, 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 , R 16 , R 17 , R 18 and R 19 Definitions, including preferred definitions, are provided for: Any of the definitions given below for any one of these substituents may be combined with any definition of any other substituent given below or elsewhere in this specification.

[0057] Preferably, X 1 CR 1 and N + -O - , more preferably CR 1 is selected from.

[0058] Preferably, X2 CR 17 and nitrogen, more preferably nitrogen.

[0059] Preferably, X 3 CR 18 and nitrogen, more preferably CR 18 is selected from.

[0060] Preferably, X 4 CR 19 and nitrogen, more preferably CR 19 is selected from.

[0061] Preferably, X 2 , X 3 , and X 4 Provided that at most one of the elements is nitrogen.

[0062] Preferably, Y is CH.

[0063] Preferably, B is selected from O, NH and NMe, more preferably B is O and NMe, even more preferably B is O.

[0064] Preferably, n is an integer of 1 to 2, and more preferably, n is 2.

[0065] Preferably, R 1 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, more preferably hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl, C 1 ~C 2 Haloalkyl, most preferably, is selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl.

[0066] Preferably, R 2 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, more preferably hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl, C 1 ~C 2 haloalkyl, most preferably selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl; or Preferably, R 2 and R 19 together with the carbon atom to which they are attached, R 16 and optionally containing 1 or 2 oxygen atoms, forming a 5-membered saturated ring which may be substituted with 1 to 2 groups represented by the following formula:

[0067] In one set of embodiments, R 2 is hydrogen, halogen, cyano, nitro, C 2 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkyl sulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 Alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, Aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkyl sulfonyl amino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 is selected from.

[0068] Preferably, R 2 is hydrogen, halogen, C 2 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 More preferably, R is selected from haloalkoxy. 2 is hydrogen, fluorine, chlorine, C 2 ~C 4 Alkyl, and C 1 ~C2 Even more preferably, R is selected from haloalkyl. 2 is selected from hydrogen, fluorine, chlorine, and trifluoromethyl.

[0069] Preferably, R 3 is selected from hydrogen, chlorine and fluorine, more preferably hydrogen and fluorine.

[0070] Preferably, R 4 is selected from hydrogen, chlorine, bromine, cyano and aminothiocarbonyl, more preferably chlorine, bromine and cyano, most preferably chlorine.

[0071] Preferably, each R 6 and R 7 is hydrogen, halogen, C 1 ~C 4 Alkyl and C 1 ~C 4 Alkoxycarbonyl, more preferably hydrogen, halogen and C 1 ~C 2 Alkyl, most preferably, is independently selected from hydrogen, chlorine and methyl.

[0072] Preferably, R 8 OR 9 It is.

[0073] Preferably, R 9 is hydrogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 2 Alkoxy C 1 ~C 2 Alkyl, Phenyl C 1 ~C 2 Alkyl and R 13 Phenyl C substituted with 1 to 2 groups represented by 1 ~C 2 Alkyl, more preferably hydrogen, C 1 ~C 4 Alkyl, C 1 ~C2 Alkoxy C 1 ~C 2 Alkyl and Phenyl C 1 ~C 2 Alkyl, most preferably hydrogen, C 1 ~C 4 Alkyl and Phenyl C 1 ~C 2 is selected from alkyl.

[0074] In one set of embodiments, R 9 is C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 2 Alkoxy C 1 ~C 2 Alkyl, Phenyl C 1 ~C 2 Alkyl and R 13 Phenyl C substituted with 1 to 2 groups represented by 1 ~C 2 Alkyl, more preferably C 1 ~C 4 Alkyl, C 1 ~C 2 Alkoxy C 1 ~C 2 Alkyl and Phenyl C 1 ~C 2 Alkyl, most preferably C 1 ~C 4 Alkyl and Phenyl C 1 ~C 2 is selected from alkyl.

[0075] Preferably, R 10 is hydrogen and SO 2 R 14 , more preferably SO 2 R 14 is selected from.

[0076] Preferably, R 11 is hydrogen.

[0077] Preferably, R12 is hydrogen, C 1 ~C 2 Alkyl and C 1 ~C 2 Alkylcarbonyl is more preferably selected from hydrogen and methyl.

[0078] Preferably, R 13 is a halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, cyano and C 1 ~C 4 alkylsulfonyl.

[0079] Preferably, R 14 is C 1 ~C 4 Alkyl and C 1 ~C 4 Alkyl(C 1 ~C 4 isopropyl(methyl)amino, more preferably methyl and isopropyl(methyl)amino.

[0080] Preferably, each R 15 is hydrogen, halogen and C 1 ~C 2 It is independently selected from alkyl, more preferably hydrogen and methyl, most preferably hydrogen.

[0081] Preferably, R 16 is a halogen, more preferably fluorine.

[0082] Preferably, R 17 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4Haloalkoxy, more preferably hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl, C 1 ~C 2 Haloalkyl, most preferably, is selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl.

[0083] Preferably, R 18 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, more preferably hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl, C 1 ~C 2 Haloalkyl, most preferably, is selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl.

[0084] Preferably, R 19 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, more preferably hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl, C 1 ~C 2 Haloalkyl, most preferably, is selected from hydrogen, fluorine, chlorine, methyl, difluoromethyl, trifluoromethyl and 1,1-difluoroethyl.

[0085] X 1 , X 2 , X 3 , and X 4 In embodiments where two of X are nitrogen, preferably 2 Or X 3 is nitrogen. X1 , X 2 , X 3 , and X 4 In embodiments where one of X is nitrogen, preferably 2 is nitrogen.

[0086] A preferred subset of compounds are X 1 CR 1 and; X 2 is nitrogen; X 3 CR 18 and; X 4 CR 19 and; Y is CH; B is O; n is 1 or 2; R 1 However, hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl and C 1 ~C 2 haloalkyl; R 2 However, hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl and C 1 ~C 2 haloalkyl; R 3 is selected from hydrogen, chlorine and fluorine; R 4 is selected from chlorine, bromine and cyano; Each R 6 and R 7 However, hydrogen, halogens and C 1 ~C 2 independently selected from alkyl; R 8 OR 9 and; R 9 But hydrogen, C 1 ~C 4 Alkyl, C 1 ~C 2 Alkoxy C 1 ~C 2Alkyl and Phenyl C 1 ~C 2 alkyl; R 18 However, hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl and C 1 ~C 2 haloalkyl; R 19 However, hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl and C 1 ~C 2 Selected from haloalkyl It is something.

[0087] Another preferred subset of compounds is X 1 CR 1 and; X 2 CR 17 and; X 3 is nitrogen; X 4 CR 19 and; Y is CH; B is O; n is 1 or 2; R 1 However, hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl and C 1 ~C 2 haloalkyl; R 2 and R 19 together with the carbon atom to which they are attached form a 5- or 6-membered ring which contains 1 or 2 heteroatoms selected from nitrogen, oxygen and sulfur; R 16 Substituted with 1 to 4 groups represented by R 3 is selected from hydrogen, chlorine and fluorine; R 4 is selected from chlorine, bromine and cyano; Each R 6 and R 7However, hydrogen, halogens and C 1 ~C 2 independently selected from alkyl; R 8 OR 9 and; R 9 But hydrogen, C 1 ~C 4 Alkyl, C 1 ~C 2 Alkoxy C 1 ~C 2 Alkyl and Phenyl C 1 ~C 2 alkyl; R 16 But halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, cyano and C 1 ~C 4 alkylsulfonyl; R 17 However, hydrogen, fluorine, chlorine, C 1 ~C 2 Alkyl and C 1 ~C 2 Selected from haloalkyl It is something.

[0088] A more preferred subset of compounds are X 1 CR 1 and; X 2 is nitrogen; X 3 CR 18 and; X 4 CR 19 and; Y is CH; B is O; n is 2; R 1 is selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl; R 2 is selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl; R 3 is selected from hydrogen and fluorine; R 4 is chlorine; Each R 6 and R 7 is independently selected from hydrogen, chlorine, and methyl; R 8 OR 9 and; R 9 But hydrogen, C 1 ~C 4 Alkyl and Phenyl C 1 ~C 2 alkyl; R 18 is selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl; R 19 is selected from hydrogen, fluorine, chlorine, methyl, difluoromethyl, trifluoromethyl and 1,1-difluoroethyl; It is something.

[0089] Another more preferred subset of compounds is X 1 CR 1 and; X 2 CR 17 and; X 3 is nitrogen; X 4 CR 19 and; Y is CH; B is O; n is 2; R 1 is selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl; R 2 and R 19 together with the carbon atom to which they are attached, R 16forming a saturated 5-membered ring containing 1 or 2 oxygen atoms, substituted with 1 to 3 groups represented by R 3 is selected from hydrogen and fluorine; R 4 is chlorine; Each R 6 and R 7 is independently selected from hydrogen, chlorine, and methyl; R 8 OR 9 and; R 9 But hydrogen, C 1 ~C 4 Alkyl and Phenyl C 1 ~C 2 alkyl; R 16 is a halogen; R 17 is selected from hydrogen, fluorine, chlorine, methyl and trifluoromethyl; It is something.

[0090] In one embodiment, the compound of formula (I), X 1 is C-Cl; X 2 is nitrogen; X 3 is CH; X 4 C-CF 3 and; Y is CH or nitrogen; R 2 is hydrogen; R 3 is hydrogen or fluorine; R 4 is chlorine; R 6 and R 7 are each independently selected from hydrogen and methyl; R 8 OR 9 and; R 9 C 1 ~C 2 (It is alkyl) The compound of formula (1) is provided.

[0091] Example Table Table 1 below shows compounds of formula (I) (wherein R 3 is hydrogen, and R 4 is chlorine, Y is CH, and B is oxygen.

[0092] [Table 1] JPEG2025507086000004.jpg250159 JPEG2025507086000005.jpg249159 JPEG2025507086000006.jpg250156 JPEG2025507086000007.jpg251158 JPEG2025507086000008.jpg250160 JPEG2025507086000009.jpg249157 JPEG2025507086000010.jpg249156 JPEG2025507086000011.jpg250158 JPEG2025507086000012.jpg250157 JPEG2025507086000013.jpg250159 JPEG2025507086000014.jpg249157 JPEG2025507086000015.jpg251159 JPEG2025507086000016.jpg250158 JPEG2025507086000017.jpg251159 JPEG2025507086000018.jpg249158 JPEG2025507086000019.jpg251159 JPEG2025507086000020.jpg251159 JPEG2025507086000021.jpg250158 JPEG2025507086000022.jpg248156 JPEG2025507086000023.jpg250156 JPEG2025507086000024.jpg250158 JPEG2025507086000025.jpg248158 JPEG2025507086000026.jpg251158 JPEG2025507086000027.jpg250156 JPEG2025507086000028.jpg115165

[0093] Formula (I) (wherein, R 3 is fluorine, R 4 is chlorine, Y is CH, B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 2-1 to 2-1140, respectively.

[0094] Formula (I) (wherein, R 3 is chlorine, R 4 is chlorine, Y is CH, B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 3-1 to 3-1140, respectively.

[0095] Formula (I) (wherein, R 3 is hydrogen, and R 4is bromine, Y is CH, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 4-1 to 4-1140, respectively.

[0096] Formula (I) (wherein, R 3 is fluorine, R 4 is bromine, Y is CH, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 5-1 to 5-1140, respectively.

[0097] Formula (I) (wherein, R 3 is chlorine, R 4 is bromine, Y is CH, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 6-1 to 6-1140, respectively.

[0098] Formula (I) (wherein, R 3 is hydrogen, and R 4 is cyano, Y is CH, B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 7-1 to 7-1140, respectively.

[0099] Formula (I) (wherein, R 3 is fluorine, R 4 is cyano, Y is CH, B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 8-1 to 8-1140, respectively.

[0100] Formula (I) (wherein, R 3 is chlorine, R 4 is cyano, Y is CH, B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 9-1 to 9-1140, respectively.

[0101] Formula (I) (wherein, R 3 is hydrogen, and R 4 is chlorine, Y is nitrogen, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 10-1 to 10-1140, respectively.

[0102] Formula (I) (wherein, R 3 is fluorine, R 4 is chlorine, Y is nitrogen, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 11-1 to 11-1140, respectively.

[0103] Formula (I) (wherein, R 3 is chlorine, R 4 is chlorine, Y is nitrogen, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 12-1 to 12-1140, respectively.

[0104] Formula (I) (wherein, R 3 is hydrogen, and R 4 is bromine, Y is nitrogen, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 13-1 to 13-1140, respectively.

[0105] Formula (I) (wherein, R 3 is fluorine, R 4 is bromine, Y is nitrogen, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 14-1 to 14-1140, respectively.

[0106] Formula (I) (wherein, R 3 is chlorine, R 4is bromine, Y is nitrogen, B is oxygen, and X is 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 15-1 to 15-1140, respectively.

[0107] Formula (I) (wherein, R 3 is hydrogen, and R 4 is cyano, Y is nitrogen, B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 16-1 to 16-1140, respectively.

[0108] Formula (I) (wherein, R 3 is fluorine, R 4 is cyano, Y is nitrogen, B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 17-1 to 17-1140, respectively.

[0109] Formula (I) (wherein, R 3 is chlorine, R 4 is cyano, Y is nitrogen, B is oxygen, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 18-1 to 18-1140, respectively.

[0110] Formula (I) (wherein, R 3 is hydrogen, and R 4 is chlorine, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 19-1 to 19-1140, respectively.

[0111] Formula (I) (wherein, R 3 is fluorine, R 4 is chlorine, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 20-1 to 20-1140, respectively.

[0112] Formula (I) (wherein, R 3 is chlorine, R 4 is chlorine, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 21-1 to 21-1140, respectively.

[0113] Formula (I) (wherein, R 3 is hydrogen, and R 4is bromine, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 22-1 to 22-1140, respectively.

[0114] Formula (I) (wherein, R 3 is fluorine, R 4 is bromine, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 23-1 to 23-1140, respectively.

[0115] Formula (I) (wherein, R 3 is chlorine, R 4 is bromine, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 24-1 to 24-1140, respectively.

[0116] Formula (I) (wherein, R 3 is hydrogen, and R 4 is cyano, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 25-1 to 25-1140, respectively.

[0117] Formula (I) (wherein, R 3 is fluorine, R 4 is cyano, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 26-1 to 26-1140, respectively.

[0118] Formula (I) (wherein, R 3 is chlorine, R 4 is cyano, Y is CH, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 27-1 to 27-1140, respectively.

[0119] Formula (I) (wherein, R 3 is hydrogen, and R 4 is chlorine, Y is nitrogen, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 28-1 to 28-1140, respectively.

[0120] Formula (I) (wherein, R 3 is fluorine, R 4is chlorine, Y is nitrogen, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 29-1 to 29-1140, respectively.

[0121] Formula (I) (wherein, R 3 is chlorine, R 4 is chlorine, Y is nitrogen, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 30-1 to 30-1140, respectively.

[0122] Formula (I) (wherein, R 3 is hydrogen, and R 4 is bromine, Y is nitrogen, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 31-1 to 31-1140, respectively.

[0123] Formula (I) (wherein, R 3 is fluorine, R 4 is bromine, Y is nitrogen, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 32-1 to 32-1140, respectively.

[0124] Formula (I) (wherein, R 3 is chlorine, R 4 is bromine, Y is nitrogen, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 33-1 to 33-1140, respectively.

[0125] Formula (I) (wherein, R 3 is hydrogen, and R 4 is cyano, Y is nitrogen, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 34-1 to 34-1140, respectively.

[0126] Formula (I) (wherein, R 3 is fluorine, R 4 is cyano, Y is nitrogen, B is NH, and X 1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 35-1 to 35-1140, respectively.

[0127] Formula (I) (wherein, R 3 is chlorine, R 4 is cyano, Y is nitrogen, B is NH, and X1 , X 2 , X 3 , X 4 , R 2 , D and R 8 The 1140 compounds in the above formula (the values ​​of which are as shown in Table 1 for compounds 1-1 to 1-1140) are represented as compound numbers 36-1 to 36-1140, respectively.

[0128] The compounds of the present invention can be prepared by techniques known to those skilled in the art of organic chemistry. General methods for preparing compounds of formula (I) are described below. Unless otherwise specified in the text, the substituent X 1 , X 2 , X 3 , X 4 , 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 and R 19 is as defined herein above. The starting materials used for the preparation of the compounds of the present invention can be purchased from ordinary commercial suppliers or prepared by known methods. The starting materials and intermediates can be purified by conventional techniques, such as chromatography, crystallization, distillation and filtration, prior to use in the next step.

[0129] Compounds of formula (I) can be prepared from compounds of formula (A) and formula (B) as shown in Reaction Scheme 1.

[0130] Reaction Scheme 1 [ka]

[0131] 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, for example S-Phos, or a preformed complex of metal and ligand, such as dppf palladium dichloride, and a base, such as potassium acetate. The boronic acid (or the corresponding boronic ester) of formula (A) is available or can be prepared by methods well known in the literature. The compound of formula (B) can be prepared from the aniline of formula (C) as shown in reaction scheme 2. Reaction Scheme 2 [ka]

[0132] For example, a compound of formula (C) can be treated with a metal halide, such as potassium iodide, and a nitrosylating agent, such as sodium nitrite and toluenesulfonic acid, in a suitable solvent, such as a mixture of water and acetonitrile. Anilines of formula (C) can be prepared from nitro compounds of formula (D) as shown in Reaction Scheme 3. Reaction Scheme 3 [ka]

[0133] For example, a compound of formula (D) can be treated with a reducing agent, such as iron and ammonium chloride, in a suitable solvent, such as a mixture of water and ethanol. Nitro compounds of formula (D) can be prepared from an acid of formula (E) and an alcohol or amine of formula (F) as shown in Reaction Scheme 4. Reaction Scheme 4 [ka]

[0134] For example, an acid of formula (E) can be treated with an activating agent such as oxalyl chloride in a suitable solvent such as dichloromethane and dimethylformamide, and the resulting intermediate is then treated with an alcohol or amine of formula (F) in the presence of a base such as triethylamine in a suitable solvent such as dichloromethane. The alcohols and amines of formula (F) are available or can be prepared by methods well known in the literature. The acids of formula (E) are available or can be prepared by methods well known in the literature. Alternatively, compounds of formula (I) can be prepared from an alcohol or amine of formula (F) and an acid of formula (G) as shown in Reaction Scheme 5. Reaction Scheme 5 [ka]

[0135] For example, an acid of formula (G) can be treated with an activating agent such as oxalyl chloride in a suitable solvent such as dichloromethane and dimethylformamide, and the resulting intermediate can then be treated with an alcohol or amine of formula (F) in the presence of a base, such as triethylamine, in a suitable solvent such as dichloromethane. Acids of formula (G) can be prepared from esters of formula (H) as shown in Reaction Scheme 6. Reaction Scheme 6 [ka]

[0136] For example, an ester of formula (H) can be treated with sodium hydroxide in a suitable solvent, such as a mixture of water and ethanol. Esters of formula (H) can be prepared from compounds of formula (J) and compounds of formula (A) as shown in Reaction Scheme 7. Reaction Scheme 7 [ka]

[0137] For example, a mixture of a compound of formula (A) and a compound of formula (J) (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, for example S-Phos, or a preformed complex of the metal and the ligand, such as dppf palladium dichloride, and a base, such as potassium acetate. The boronic acid (or the corresponding boronic ester) of formula (A) is available or can be prepared by methods well known in the literature. The compound of formula (J) can be prepared from the aniline of formula (K) as shown in reaction scheme 8. Reaction Scheme 8 [ka]

[0138] For example, compounds of formula (K) can be treated with a metal halide, such as potassium iodide, and a nitrosylating agent, such as sodium nitrite and toluenesulfonic acid, in a suitable solvent, such as a mixture of water and acetonitrile. Anilines of formula (K) are either available or can be prepared from nitro compounds of formula (L) as shown in Reaction Scheme 9. Reaction Scheme 9 [ka]

[0139] For example, compounds of formula (L) can be treated with a reducing agent, such as iron and ammonium chloride, in a suitable solvent, such as a mixture of water and ethanol. Nitro compounds of formula (L) are either available or can be prepared by methods well known in the literature. 8 Compounds of formula (IA), which are compounds of formula (I) where R is an OH group, can be reacted with R 8 OR 9 The compound of formula (I) may be prepared from a compound of formula (IB) Reaction Scheme 10 [ka]

[0140] For example, a compound of formula (IB) can be treated with hydrochloric acid in a suitable solvent, such as dioxane. 8 NR 10 R 11 Compounds of formula (I), where: Compounds of formula (IC), can be prepared from compounds of formula (IA) as shown in Reaction Scheme 11. Reaction Scheme 11 [ka]

[0141] For example, a compound of formula (IA) may be treated with a halogenating reagent, such as oxalyl chloride, in a suitable solvent, such as dichloromethane, to form an acyl halide, which may be reacted with the reagent HNR 10 R 11 It can be processed with.

[0142] Those skilled in the art will appreciate that it is often possible to vary the order in which the transformations described above are carried out or combine them in alternative ways to prepare a wide range of compounds of formula (I). Several steps may also be combined into a single reaction. All such variations are considered to be within the scope of the present invention.

[0143] Those skilled in the art will appreciate that some reagents may be substituted with certain values ​​or substituents X as defined herein. 1 , X 2 , X 3 , X 4 , 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 , R12 , R 13 , R 14 , R 15 , R 17 , R 18 and R 19 and any additional steps, such as protection and / or deprotection steps, that are necessary to achieve the desired transformation will be apparent to one of skill in the art.

[0144] The compounds according to the present invention can be used as herbicides in unmodified form, but are generally formulated into compositions in various ways using formulation auxiliaries such as carriers, solvents and surfactants.The formulations can be in various physical forms, such as dusts, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oil dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (containing water or water-miscible organic solvents as carriers), impregnated polymer films or other forms known, for example, from Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010).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 done, for example, with water, liquid fertilizers, micronutrients, biological organisms, oils or solvents.

[0145] The formulations can be prepared, for example, by mixing the active ingredient with formulation auxiliaries to obtain a composition in the form of a finely divided solid, granules, a solution, a dispersion or an emulsion. The active ingredient can also be formulated with other auxiliaries, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surfactants or combinations thereof.

[0146] The active ingredient can also be contained in fine microcapsules. Microcapsules contain the active ingredient in a porous carrier. This allows the active ingredient to be released into the environment in controlled amounts (e.g., sustained release). Microcapsules usually have a diameter of 0.1 to 500 microns. The microcapsules contain the active ingredient in an amount of about 25 to 95% by weight of the capsule weight. The active ingredient can be in the form of a monolithic solid, in the form of fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulating membrane can include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane or chemically modified polymers and starch xanthate or other polymers known to those skilled in the art. Alternatively, fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of the substrate, but the microcapsules themselves are not encapsulated.

[0147] Formulation auxiliaries suitable for the preparation of the compositions according to the invention are known per se. Liquid carriers include water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-Heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, 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 alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc. may be used.

[0148] 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.

[0149] Many surface-active substances can be used advantageously in both solid and liquid formulations, especially in formulations which may be diluted with a carrier before use. The surface-active substances can be anionic, cationic, nonionic or polymeric and can be used 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 lauryl sulfate; salts of alkylaryl sulfonic acids, such as calcium dodecylbenzene sulfonate; alkylphenol / alkylene oxide adducts, such as nonylphenol ethoxylate; alcohol / alkylene oxide adducts, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalene sulfonic acids, such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium 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 di-alkyl phosphate esters, such as those described in, for example, McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New York, 1989. Further substances described in Jersey (1981) are also included.

[0150] Further auxiliaries which can be used in the agrochemical formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, neutralizing or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, flow regulators, lubricants, dispersants, thickeners, antifreeze agents, fungicides and liquid and solid fertilizers.

[0151] The composition according to the invention may contain an additive comprising an oil of vegetable or animal origin, a mineral oil, an alkyl ester of such an oil or a mixture of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally 0.01-10% 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 vegetable origin (e.g. rapeseed oil, olive oil or sunflower oil), emulsified vegetable oil, alkyl ester of oil of vegetable origin (e.g. methyl derivatives) or oil of animal origin (e.g. fish oil or beef tallow, etc.). Preferred oil additives are C 8 ~C 22 Alkyl esters of fatty acids, especially C 12 ~C 18 Methyl 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). Compendium of Herbicide Adjuvants, 10 th A large number of oil derivatives are known from the Journal of Chemical Industry, Vol. 13, No. 1, 2010, Issue 1, Springer-Verlag, 2010.

[0152] The herbicidal compositions generally comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of the compound of formula (I) and 1 to 99.9% by weight of formulation auxiliaries, preferably including 0 to 25% by weight of a surfactant. The compositions of the invention generally comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of the compound of the invention and 1 to 99.9% by weight of formulation auxiliaries, preferably including 0 to 25% by weight of a surfactant. Commercial products may preferably be formulated as concentrates, but end users will usually use dilute formulations.

[0153] Application rates vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing climatic conditions and other factors governed by the method of application, the time of application and the target crop. As a general guideline, the compounds may be applied at a rate of 1-2000 l / ha, especially 10-1000 l / ha.

[0154] A preferred formulation may have the following composition (% by weight):

[0155] Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1-30%, preferably 5-20% Liquid carrier: 1-80%, preferably 1-35%

[0156] Spraying agent: Active ingredient: 0.1-10%, preferably 0.1-5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0157] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30%

[0158] Wettable powder: Active ingredient: 0.5-90%, preferably 1-80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90%

[0159] Granules: Active ingredient: 0.1-30%, preferably 0.1-15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0160] The composition of the present invention may further comprise at least one additional pesticide.For example, the compound according to the present invention may 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.

[0161] Thus, the compounds of formula (I) can be used in combination with one or more other herbicides to obtain various herbicidal mixtures. Specific examples of such mixtures (where "I" represents a compound of formula (I)) include:-I+acetochlor;I+acifluorfen (including acifluorfen-sodium);I+aclonifen;I+alachlor;I+aloxydim;I+ametryne;I+amicarbazone;I+amidosulfuron;I+aminocyclopyrachlor;I+aminopyralid;I+amitrole;I+asulam;I+atrazine;I+bensulfuron (including bensulfuron-methyl);I+bentazone;I+bicyclopyrone;I+ Bialaphos;I+Bifenox;I+Bispyribac-sodium;I+Bixlozone;I+Bromacil;I+Bromoxynil;I+Butachlor;I+Butafenacil;I+Cafenstrole;I+Carfentrazone (including carfentrazone-ethyl);Cloransulam (including cloransulam-methyl);I+Chlorimuron (including chlorimuron-ethyl);I+Chlorotoluron;I+Cinosulfuron;I+Chlorsulfuron;I+Cinmethylin;I+Cracifos;I+Clethodim;I+Clodinafop (Clethodim) I+clomazone;I+clopyralid;I+cyclopyranyl;I+cyclopyrimorate;I+cyclosulfamuron;I+cyhalofop (including cyhalofop-butyl);I+2,4-D (including choline salt and its 2-ethylhexyl ester);I+2,4-DB;I+dymron;I+desmedipham;I+dicamba (including aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium) , including potassium and sodium salts);I+Diclofop-methyl;I+Diclosulam;I+Diflufenican;I+Difenzoquat;I+Diflufenican;I+Diflufenzopyr;I+Dimethachlor;I+Dimethenamid-P;I+Diquat dibromide;I+Diuron;I+Esprocarb;I+Ethalfluralin;I+Ethofumesate;I+Fenoxaprop (including fenoxaprop-P-ethyl);I+Fenoxasulfone;I+Fenquinotrione;I+Fentrazamide;I+Flazasulfuron;I+Florasulam;I+Florpyrauxifen;I+Fluazifop (including fluazifop-p-butyl);I+Flucarbazone (including flucarbazone-sodium);;I+Flufenacet;I+Flumetralin;I+Flumetosulam;I+Flumioxazin;I+Flupyrsulfuron (including flupyrsulfuron-methyl-sodium);;I+Fluroxypyr (including fluroxypyr-meptyl);;I+Fluthiacet-methyl;I+Fomesafen;I+Foramsulfuron;I+Glufosinate (including its ammonium salt);I+Glutidine I+Haloxifene (including its diammonium, isopropylammonium and potassium salts);I+Halosulfuron-methyl;I+Haloxyfop (including haloxyfop-methyl);I+Hexazinone;I+Hydantocidin;I+Imazamox;I+Imazapic;I+Imazapyr;I+Imazaquin;I+Imazethapyr;I+Indaziflam;I+Iodosulfuron (including iodosulfuron-methyl-sodium);I+Iofensulfuron;I+Iofensulfuron-sodium;I+A Ioxynil;I+Ipfencarbazone;I+Isoproturon;I+Isoxaben;I+Isoxaflutole;I+Lactofen;I+Lancotrione;I+Linuron;I+MCPA;I+MCPB;I+Mecoprop-P;I+Mefenacet;I+Mesosulfuron;I+Mesosulfuron-methyl;I+Mesotrione;I+Metamitron;I+Metazachlor;I+Methiozoline;I+Metobromuron;I+Metolachlor;I+Metosulam;I+Metoxuron;I+Metribuzin;I+Metsulfuron;I+Molinate;I+Napropamide;I+ Nicosulfuron;I+Norflurazon;I+Orthosulfamuron;I+Oxadiargyl;I+Oxadiazon;I+Oxasulfuron;I+Oxyfluorfen;I+Paraquat dichloride;I+Pendimethalin;I+Penoxsulam;I+Fenmedipham;I+Picloram;I+Picolinafen;I+Pinoxaden;I+Pretilachlor;I+Primisulfuron-methyl;I+Prodiamine;I+Prometryn;I+Propachlor;I+Propanil;I+Propaquizafop;I+Propham;I+Propyrisulfuron, I+Propyzamide;I+Prosulfocarb;I+Prosulfuron;I+Pyraclonil;I+Pyraflufen (including pyraflufen-ethyl);I+Pyrasulfotole;I+Pyrazolinate, I+Pyrazosulfuron-ethyl;I+Pyribenzoxime;I+Pyridate;I+Pyriftalid;I+Pyrimisulfan, I+Pyrithiobac-sodium;I+Pyroxasulfone;I+Pyroxsulam;I+Quinclorac;I+Quinmelac;I+Quizalofop (including quizalofop-p-ethyl and quizalofop-p-tefuryl);I+Li Musulfuron;I+Saflufenacil;I+Sethoxydim;I+Simazine;I+S-Metolachlor;I+Sulcotrione;I+Sulfentrazone;I+Sulfosulfuron;I+Tebuthiuron;I+Tefuryltrione;I+Tembotrione;I+Terbuthylazine;I+Terbutryn;I+Thiencarbazone;I+Thiefensulfuron;I+Thiafenacil;I+Tolpyralate;I+Topramezone;I+Tralkoxydim;I+Triafamone;I+Trialate;I+Triasulfuron;I+Tribenuron (Tribe I+Triclopyr;I+Trifloxysulfuron (including trifloxysulfuron-sodium);I+Trifludimoxadine;I+Trifluralin;I+Triflusulfuron;I+Tritosulfuron;I+4-Hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;I+4-Hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;I+5-Ethoxy-4-hydroxy- I+4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;I+4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]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]cyclohexane-1,3-dione;I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione phenyl)-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]-5-ethyl-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 ... 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;

[0162] The mixing partners of the 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.

[0163] The compounds of formula (I) may also be used in mixtures with other agricultural chemicals such as fungicides, nematicides or insecticides (examples of which are given in The Pesticide Manual).

[0164] The mixing ratio of the compound of formula (I) to the mixing partners is preferably 1:100 to 1000:1.

[0165] The mixtures can be advantageously used in the abovementioned formulations (in which case "active ingredient" relates to the respective mixture of the compound of formula (I) with the mixing partner).

[0166] The compound of formula (I) of the present invention can also be used in combination with herbicide safeners.Preferred combinations (wherein "I" represents the compound of formula (I)) include: I+benoxacor, I+cloquintocet (including cloquintocet-mexyl);I+cyprosulfamide;I+dichlormid;I+fenchlorazole (including fenchlorazole-ethyl);I+fenclorim;I+fluxofenim;I+furilazoleI+isoxadifen (including isoxadifen-ethyl);I+mefenpyr (including mefenpyr-diethyl);I+methocamiphen;I+N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide and I+oxabetrinil.

[0167] Mixtures of compounds of formula (I) with cyprosulfamide, isoxadifen (including isoxadifen-ethyl), cloquintocet (including cloquintocet mexyl) and / or N-(2-methoxybenzoyl)-4-[(methyl-aminocarbonyl)amino]benzenesulfonamide are especially preferred.

[0168] The safener of the compound of formula (I) is, for example, th Edition (BCPC), 2006. A reference to cloquintocet-mexyl also applies to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, and a reference to fenchlorazole-ethyl also applies to fenchlorazole, etc., as disclosed in WO 02 / 34048.

[0169] Preferably, the mixing ratio of the compound of formula (I) to the safener is from 100:1 to 1:10, in particular from 20:1 to 1:1.

[0170] The mixtures may be advantageously used in the formulations described above, where "active ingredient" refers to the respective mixture of compound of formula (I) and safener.

[0171] The compounds of formula (I) of the present invention are useful as herbicides. Thus, the present invention further includes a method for controlling unwanted plants, which comprises applying an effective amount of the compounds of the present invention or a herbicidal composition containing said compounds to said plants or to the habitat containing them. "Control" means killing, reducing or retarding growth, or preventing or reducing germination. Generally, the plants to be controlled are unwanted plants (weeds). "Habitat" means the area where the plants are growing or will grow.

[0172] The application rates of the compounds of formula (I) may vary within a wide range and depend on the nature of the soil, the method of application (pre-emergence; post-emergence; application in the furrow; no-tillage application, etc.), the crop plants, the weeds to be controlled, the prevailing climatic conditions, as well as the application method, time of application and other factors governed by the target crop. The compounds of formula (I) according to the invention are generally applied at a rate of 10 to 2000 g / ha, in particular 50 to 1000 g / ha. A preferred range is 10 to 200 g / ha.

[0173] Application is generally made by spraying the composition, usually with a tractor-mounted sprayer for large areas, although other methods such as dusting (for dusts), dripping or irrigation can also be used.

[0174] Useful plants in which the compositions according to the invention can be used include crops such as cereals, e.g. barley and wheat, cotton, oilseed rape, sunflower, corn, rice, soybeans, sugar beets, sugar cane and turf.

[0175] Crop plants can also include trees such as fruit trees, palm trees, coconut trees or other nuts, as well as vines such as grapes, fruit bushes, fruit plants and vegetables.

[0176] Crops should also be understood to include crops that have been made tolerant to herbicides or classes of herbicides (e.g., ALS-, GS-, EPSPS-, PPO-, ACCase- and HPPD-inhibitors) by conventional breeding methods or genetic engineering. An example of a crop that has been made tolerant to imidazolinones, such as imazamox, by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been made tolerant to herbicides by genetic engineering methods include, for example, glyphosate- and glufosinate-tolerant corn varieties available under the trade names RoundupReady® and LibertyLink®.

[0177] The compounds of the present invention can be used in a method for controlling undesirable vegetation in crop plants that are resistant to protoporphyrinogen oxidase (PPO) inhibitors. Such plants can be obtained, for example, by transforming crop plants with a nucleic acid encoding a suitable protoporphyrinogen oxidase, which may contain a mutation to make them more resistant to PPO inhibitors. Examples of such nucleic acids and crop plants are described 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 2015 / 092707, WO 2015 / 092709, WO 2015 / 092708, WO 2015 / 092709 ... These compounds are disclosed in WO 6 / 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. Accordingly, the present invention also provides a method for controlling undesirable vegetation in a locus of plant cultivation, comprising the steps of: a) providing to said locus a plant comprising at least one nucleic acid comprising a nucleotide sequence encoding a PPO polypeptide that is resistant or tolerant to a "protoporphyrinogen oxidase (PPO)-inhibiting herbicide"; and b) applying to said locus an effective amount of said herbicide, wherein the PPO-inhibiting herbicide is a compound of formula (I) as defined herein.

[0178] It should also be understood that crops are those that have been made resistant to pests by genetic engineering methods, such as Bt maize (resistant to the European corn borer), Bt cotton (resistant to the cotton weevil) and even Bt potato (resistant to the Colorado potato beetle). An example of Bt maize is the Bt176 maize hybrid from NK® (Syngenta Seeds). Bt toxins are proteins that are naturally formed by the Bacillus thuringiensis soil bacterium. Examples of toxins or transgenic plants capable of synthesizing such toxins are described in EP 451878, EP 374753, WO 93 / 07278, WO 95 / 34656, WO 03 / 052073 and EP 427529. Examples of transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are KnockOut® (corn), Yield Gard® (corn), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potato), NatureGard® and Protexcta®. Either the plant crop or its seed material can be resistant to herbicides and at the same time resistant to insect ingestion (a "stacked" transgenic event). For example, a seed has the ability to express an insecticidal Cry3 protein and is at the same time resistant to glyphosate.

[0179] It should also be understood that crop plants include those obtained by conventional breeding or genetic engineering methods and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavor).

[0180] Other useful plants include turfgrass grown commercially for turfgrass or lawns, for example, on golf courses, lawns, parks and roadsides, as well as ornamental plants such as flowers or shrubs.

[0181] The compounds and compositions of formula (I) of the present invention can generally be used to control a wide variety of monocotyledonous and dicotyledonous weed species. Examples of monocotyledonous species that can usually be controlled are Alopecurus myosuroides, Avena fatua, Brachiaria plantaginea, Bromus tectorum, Cyperus esculentus, Digitaria sanguinalis, Echinochloa crus-galli, Lolium perenne, Lolium multiflorum, Panicum miliaceum, Poa annua, Setaria viridis, Setaria faberi, and others. faberi and Sorghum bicolor.Examples of dicotyledonous species that can be controlled include Abutilon theophrasti, Amaranthus retroflexus, Bidens pilosa, Chenopodium album, Euphorbia heterophylla, Galium aparine, Ipomoea hederacea, Kochia scoparia, Polygonum convolvulus, Sida spinosa, Sinapis arvensis, Solanum nigrum, Stellaria media, Veronica persica, and others. persica and Xanthium strumarium.

[0182] Undesirable plants should also be understood to include those weeds that have been made tolerant to herbicides or classes of herbicides (e.g., ALS-, GS-, EPSPS-, PPO-, ACCase- and HPPD-inhibitors) by evolution, by traditional breeding methods or by genetic engineering. An example is Amaranthus palmeri, which has evolved resistance to glyphosate and / or acetolactate synthase (ALS) inhibitor herbicides.

[0183] The compounds of the present invention can be used in methods for controlling undesirable plants or weeds that are resistant to protoporphyrinogen oxidase (PPO) inhibitors. For example, Amaranthus palmeri and Amaranthus tuberculatus populations have evolved as PPO-resistant weeds due to amino acid substitutions in PPX2L, such as those occurring at amino acids R128 (also referred to as R98) and G399, or a codon (glycine) deletion in PPX2L at codon 210 (Δ210) (codon numbering is based on NCBI reference DQ386114). The compounds of the invention can be used in methods to control Amaranthus palmeri and / or Amaranthus tuberculatus having mutations or deletions in the aforementioned codons or equivalents, and it would be obvious to try the compounds to control undesirable plants or weeds having other mutations that confer tolerance or resistance to PPO inhibitors that may occur.

[0184] The compounds of formula (I) are also useful in pre-harvest drying of crops, such as, but not limited to, potatoes, soybeans, sunflowers and cotton, which are used to dry the leaves of crops to facilitate harvesting without significant damage to the crop itself.

[0185] The compounds / compositions of the present invention are particularly useful in non-selective burn down applications and may therefore also be used to control volunteer vegetation or to ward off crop plants.

[0186] 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. EXAMPLES

[0187] The following examples are intended to illustrate, but not limit, the present invention.

[0188] Synthesis Example Example 1 Preparation of [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-fluoro-benzoate (Compound 2-525; S-enantiomer) Step 1: Synthesis of 5-bromo-2-chloro-4-fluoro-benzoic acid [ka] Sulfur (150 mg, 4.6 mmol) and bromine (0.5 ml, 9.8 mmol) were added to a stirred solution of 2-chloro-4-fluoro-benzoic acid (3.4 g, 19 mmol) in chlorosulfonic acid (15 ml) at ambient temperature. The resulting mixture was heated at 70° C. for 4 hours, then cooled and added slowly to ice water (300 ml). The resulting mixture was extracted with ethyl acetate (200 ml) and the organic extract was dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 5-bromo-2-chloro-4-fluoro-benzoic acid as a white solid (4.7 g). 1 H NMR (400 MHz, CDCl 3 ) δ 7.3 (d, 1H), 7.25 (dd, 1H ppm (no acid protons observed).

[0189] Step 2: Synthesis of [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 5-bromo-2-chloro-4-fluoro-benzoate [ka] Oxalyl chloride (0.45 ml, 5.1 mmol) was added dropwise to a stirred solution of 5-bromo-2-chloro-4-fluoro-benzoic acid (0.90 g, 3.4 mmol) in dichloromethane (20 ml) at ambient temperature. The resulting solution was stirred at room temperature for 5 minutes, then dimethylformamide (5 drops) was added and the resulting solution was stirred for a further 60 minutes. The solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane (20 ml). To this solution was added a solution of triethylamine (0.52 ml, 3.7 mmol) and ethyl (3S)-3-hydroxybutanoate (0.49 g, 3.7 mmol) in dichloromethane (5 ml), the resulting mixture was stirred at ambient temperature for 1 hour, then evaporated under reduced pressure and the residue purified by chromatography to give [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 5-bromo-2-chloro-4-fluoro-benzoate as an oil (1.1 g).

[0190] Following this general method the following were also prepared: [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 5-bromo-2-chloro-benzoate [(1R)-3-ethoxy-1-methyl-3-oxo-propyl] 5-bromo-2-chloro-4-fluoro-benzoate

[0191] Step 3: Synthesis of [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ka] Potassium acetate (0.8 g, 8 mmol) and palladium dichloride (dppf) (0.2 g, 0.27 mmol) were added to a stirred solution of [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 5-bromo-2-chloro-4-fluoro-benzoate (980 mg, 2.7 mmol) and bis(pinacolato)diboron (1.0 g, 4 mmol) in dioxane (20 ml). The resulting mixture was heated in a microwave oven at 100° C. for 45 minutes and then allowed to cool. Ethyl acetate (100 ml) was added, the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by chromatography to give [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (650 mg).

[0192] Following this general method the following were also prepared: [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [(1R)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

[0193] Step 4: Synthesis of [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-fluoro-benzoate (compound 2-525; S-enantiomer) [ka] Potassium acetate (0.23 g, 0.23 mmol) and palladium dichloride (dppf) (55 mg, 0.075 mmol) were added to a stirred solution of [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (620 mg, 0.75 mmol) and 2,3-dichloro-5-(trifluoromethyl)-pyridine (0.25 g, 1.1 mmol) in dioxane (12 ml). The resulting mixture was heated in a microwave oven at 100° C. for 45 minutes and then allowed to cool. Ethyl acetate (10 ml) was added, the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by chromatography to give [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-fluoro-benzoate (compound 2-525; S-enantiomer) as a gum (86 mg). 1 H NMR (400 MHz, CDCl 3 )δ 8.9(s,1H),8.1(s,1H),8.0(d,1H),7.35(d,1H),5.55(m,1H),4.15(q,2H),2.8(dd,1H),2.65(dd,1H),1.45(d,3H),1.2(t,3H)ppm.

[0194] Following this general method the following were also prepared: [(1S)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-benzoate (compound 1-525; S-enantiomer): 1 H NMR (400 MHz, CDCl 3 )δ 8.85(s,1H),8.25(s,1H),8.1(s,1H),7.85(d,1H),7.6(d,1H),5.6(m,1 H),4.15(q,2H),2.8(dd,1H),2.65(dd,1H),1.45(d,3H),1.2(t,3H)ppm.

[0195] [(1R)-3-ethoxy-1-methyl-3-oxo-propyl] 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-fluoro-benzoate (compound 2-525; R-enantiomer): 1 H NMR (400 MHz, CDCl 3 )δ 8.9(s,1H),8.1(s,1H),8.0(d,1H),7.35(d,1H),5.55(m,1H),4.15(q,2H),2.8(dd,1H),2.6(dd,1H),1.5(d,3H),1.2(t,3H)ppm.

[0196] Example 2 Preparation of (3-ethoxy-1-methyl-3-oxo-propyl) 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoate (Compound 1-525) Step 1: Synthesis of methyl 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoate [ka] Potassium acetate (2.95 g, 30 mmol) and palladium dichloride (dppf) (730 mg, 0.98 mmol) were added to a stirred solution of (4-chloro-3-methoxycarbonyl-phenyl)-boronic acid (2.2 g, 9.8 mmol) and 2,3-dichloro-5-(trifluoromethyl)-pyridine (3.2 g, 15 mmol) in dioxane (13 ml). The resulting mixture was heated in a microwave oven at 100° C. for 45 minutes, then allowed to cool and evaporated. Dichloromethane (10 ml) was added and the mixture was washed with water and evaporated under reduced pressure. The residue was purified by chromatography to give methyl 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoate as a pale orange oil (3.2 g). 1 H NMR (400 MHz, CDCl 3 )δ 8.85(s,1H),8.3(d,1H),8.1(s,1H),7.85(dd,1H),7.6(d,1H),3.95(s,3H)ppm.

[0197] Step 2: Synthesis of 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoic acid [ka] Aqueous sodium hydroxide (1N; 1.7 ml, 1.7 mmol) was added to a stirred solution of methyl 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoate (300 mg, 0.86 mmol) in methanol (5 ml) at ambient temperature. The resulting mixture was stirred at ambient temperature for 17 hours and then evaporated under reduced pressure. Water was added to the residue and the mixture was washed with ethyl acetate. Hydrochloric acid (2N) was added to bring the pH to 2 and the mixture was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoic acid as a white solid (250 mg). 1 H NMR (400 MHz, CDCl 3 ) δ 8.9(s,1H), 8.35(s,1H), 8.15(s,1H), 7.9(d,1H), 7.6(d,1H) ppm (no acid protons observed).

[0198] Step 3: Preparation of (3-ethoxy-1-methyl-3-oxo-propyl) 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoate (compound 1-525) [ka] Thionyl chloride (0.11 ml, 1.5 mmol) was added dropwise to a stirred solution of 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoic (250 mg, 0.74 mmol) in toluene (5 ml) at ambient temperature. The resulting solution was heated at reflux for 1 h and then allowed to cool. The solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane (20 ml). This solution was added to a stirred solution of triethylamine (0.05 ml, 0.34 mmol) and ethyl 3-hydroxybutanoate (77 mg, 0.56 mmol) in dichloromethane (5 ml). The resulting mixture was stirred at ambient temperature for 4 hours, then evaporated under reduced pressure, and the residue was purified by chromatography to give (3-ethoxy-1-methyl-3-oxo-propyl) 2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]benzoate (compound 1-525) as an oil (30 mg). 1 H NMR (400 MHz, CDCl 3 )δ 8.85(s,1H),8.25(d,1H),8.1(s,1H),7.85(dd,1H),7.6(d,1H),5.6(m,1 H),4.15(q,2H),2.8(dd,1H),2.65(dd,1H),1.45(d,3H),1.2(t,3H)ppm.

[0199] Example 3 Preparation of [(1S)-3-Methoxy-1-methyl-3-oxo-propyl] 3-chloro-6-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-5-fluoro-pyridine-2-carboxylate (Compound 11-524; S-enantiomer) Step 1: Synthesis of [(1S)-3-methoxy-1-methyl-3-oxo-propyl] 6-bromo-3-chloro-5-fluoro-pyridine-2-carboxylate [ka] Oxalyl chloride (1 ml, 12 mmol) was added dropwise to a stirred solution of 6-bromo-3-chloro-5-fluoro-pyridine-2-carboxylic acid (1.5 g, 5.9 mmol) in dichloromethane (30 ml) at ambient temperature. The resulting solution was stirred at 0° C. for 5 minutes, then dimethylformamide (3 drops) was added and the resulting solution was stirred at ambient temperature for a further 2 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in acetonitrile (12 ml). This solution was added dropwise to a solution of pyridine (2.4 ml, 30 mmol) and ethyl (3S)-3-hydroxybutanoate (0.98 g, 8.3 mmol) in acetonitrile (30 ml). The resulting mixture was stirred at 0° C. for 10 minutes and then at ambient temperature for 17 hours. Water was added followed by concentrated hydrochloric acid to bring the pH to 1. The mixture was extracted twice with ethyl acetate and the combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give [(1S)-3-methoxy-1-methyl-3-oxo-propyl] 6-bromo-3-chloro-5-fluoro-pyridine-2-carboxylate (2.1 g). 1 H NMR (400 MHz, CDCl 3 )δ 7.55(d,1H),5.6(m,1H),3.7(s,3H),2.85(dd,1H),2.65(dd,1H),1.5(d,3H)ppm.

[0200] Step 2: Synthesis of [(1S)-3-methoxy-1-methyl-3-oxo-propyl] 3-chloro-6-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-5-fluoro-pyridine-2-carboxylate (compound 11-524; S-enantiomer) [ka] [(1S)-3-Methoxy-1-methyl-3-oxo-propyl] 6-bromo-3-chloro-5-fluoro-pyridine-2-carboxylate (0.25 g, 0.71 mmol), bis(triphenylphosphine)palladium dichloride (40 mg, 0.06 mmol) and copper(I) iodide (21 mg, 0.11 mmol) were added to a stirred solution of [3-chloro-5-(trifluoromethyl)-2-pyridyl]-trimethyl-stannane (prepared as described in Example 4; 640 mg, 1.1 mmol) in toluene (5 ml). The resulting mixture was heated at 100° C. for 2.5 hours, then allowed to cool and evaporated. The residue was purified by chromatography to give [(1S)-3-methoxy-1-methyl-3-oxo-propyl] 3-chloro-6-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-5-fluoro-pyridine-2-carboxylate (compound 11-524; S-enantiomer) as a yellow oil (184 mg). 1 H NMR (400 MHz, CDCl 3 )δ 8.9(s,1H),8.1(s,1H),7.75(d,1H),5.6(m,1H),3.7(s,3H),2.85(dd,1H),2.65(dd,1H),1.5(d,3H)ppm.

[0201] Example 4 Preparation of [3-chloro-5-(trifluoromethyl)-2-pyridyl]-trimethyl-stannane [ka] 3-Chloro-2-iodo-5-(trifluoromethyl)-pyridine (1.0 g, 3.3 mmol) and bis(triphenylphosphine)palladium dichloride (230 mg, 0.33 mmol) were added to a stirred solution of hexamethylditin (1.3 g, 3.9 mmol) in dioxane (10 ml). The resulting mixture was heated at 100° C. for 2 hours, then allowed to cool, filtered and evaporated under reduced pressure to give [3-chloro-5-(trifluoromethyl)-2-pyridyl]-trimethyl-stannane as a brown oil (2.0 g). 1 H NMR (400 MHz, CDCl 3)δ 8.85(s,1H),7.75(s,1H),0.45(t,9H)ppm.

[0202] Formulation Examples

[0203] [Table 2]

[0204] The combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to give a wettable powder which can be diluted with water to give a suspension of the desired concentration.

[0205] emulsifiable concentrate Active ingredient 10% Octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene Mixture 50%

[0206] Emulsions of any required dilution rate which can be used for plant protection can be obtained from this concentrate by dilution with water.

[0207] [Table 3]

[0208] Ready-to-use powders are obtained by mixing the combination with a carrier and grinding the mixture in a suitable mill.

[0209] Extrusion Granules Active ingredient 15% Sodium Lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0210] The combination is mixed with the auxiliaries and ground, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0211] Coated Granules Active ingredient: 8% Polyethylene glycol (mol.wt.200) 3% Kaolin 89%

[0212] In a mixer, the finely ground combination is applied uniformly to the kaolin moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

[0213] Suspension concentrate Active ingredient 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium Lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0214] The finely ground combination is thoroughly mixed with the adjuvant to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.

[0215] Slow-release capsule suspension 28 parts of the combination are mixed with 2 parts of aromatic solvent and 7 parts of toluene diisocyanate / polymethylene-polyphenylisocyanate-mixture (8:1). The mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of defoamer and 51.6 parts of water until the desired particle size is achieved. A mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water is added to the emulsion. The mixture is stirred until the polymerization reaction is complete.

[0216] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% active ingredient. The medium capsule diameter is 8-15 microns.

[0217] The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for the purpose.

[0218] Biological Examples Pre-emergence biological efficacy Weed and / or crop seeds were sown in standard soil in pots (Amaranthus palmeri (AMAPA), Lolium perenne (LOLPE), Euphorbia heterophylla (EPHHL), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE)). After one day of cultivation under controlled conditions in a greenhouse (24 / 19°C, day / night; 16 hours of light), the plants were sprayed with a spray solution derived from a formulation of the technical active ingredient 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 obtain the desired final dose of the test compound. Unless otherwise stated, the compounds were applied at 250 g / ha. The test plants were then grown under controlled conditions in a greenhouse (24 / 18°C, day / night; 15 hours of light; 50% humidity) and watered twice a day. After 13 days, the test was evaluated (100 = total damage to the plants; 0 = no damage to the plants). The results are shown in Table 2 below.

[0219] [Table 4]

[0220] Post-germination biological efficacy Weed and / or crop seeds were sown in standard soil in pots (Amaranthus palmeri (AMAPA), (CHEAL), Euphorbia heterophylla (EPHHL), Ipomoea hederacea (IPOHE), Eleusine indica (ELEIN), Lolium perenne (LOLPE), Digitaria sanguinalis (DIGSA), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG)). After 14 days of cultivation under controlled conditions in a greenhouse (24 / 19°C, day / night; 16 hours of light), the plants were sprayed with a spray solution derived from a formulation of the technical active ingredient 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 obtain the desired final dose of the test compound. Unless otherwise stated, the compounds were applied at 250 g / ha. The test plants were then grown under controlled conditions in a greenhouse (24 / 18°C, day / night; 15 hours of light; 50% humidity) and watered twice a day. After 13 days, the test was evaluated (100 = total damage to the plants; 0 = no damage to the plants). The results are shown in Table 3 below.

[0221] [Table 5]

Claims

1. Formula (I): 【Chemistry 1】 (In the formula, X 1 is C-R 1 , nitrogen and N + -O - Selected from: X 2 is C-R 17 and nitrogen; X 3 is C-R 18 and nitrogen; X 4 is C-R 19 and nitrogen; However, X 1 , X 2 , X 3 and X 4 At most two of the X are nitrogen. 3 and X 4 are not both nitrogen; Y is selected from C—H and nitrogen; B is O, S and NR 5 Selected from: D is (CR 6 R 7 ) n and n is an integer from 1 to 4; R 1 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkylsulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkylsulfonylamino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 and C.O.N.R. 10 R 11 Selected from: R 2 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkylsulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkylsulfonylamino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 or R 1 and R 2 together with the carbon atoms to which they are attached form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated, which may optionally contain 1 or 2 heteroatoms selected from nitrogen, oxygen and sulfur; R 16 or R 2 and R 19 together with the carbon atoms to which they are attached form a 5- or 6-membered ring which may be saturated or partially or fully unsaturated, which may optionally contain 1 or 2 heteroatoms selected from nitrogen, oxygen and sulfur; R 16 may be substituted with 1 to 4 groups represented by R 3 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkylthio and C 1 ~C 4 alkylsulfonyl; R 4 is hydrogen, halogen, cyano, nitro, aminocarbonyl, aminothiocarbonyl, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy and C 1 ~C 4 alkylsulfonyl; R 5 is hydrogen, hydroxy, C 1 ~C 6 Alkyl and C 1 ~C 4 alkoxy; Each R 6 and R 7 is hydrogen, halogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, Hydroxy, C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkoxycarbonyl and CH 2 OR 12 where R 6 and R 7 are not both hydroxy on the same carbon atom; or two groups R 6 and R 7 are, together on the same or different carbon atoms, R 15 C containing 0, 1 or 2 oxygen atoms, substituted by 1 to 3 groups represented by 1 ~C 5 Forming an alkylene chain; or two groups R 6 and R 7 together with the carbon atom to which they are attached, C 2 may form an alkene; R 8 is OR 9 , S.R. 9 and N.R. 10 R 11 Selected from: R 9 is hydrogen, C 1 ~C 10 Alkyl, C 1 ~C 10 Haloalkyl, C 3 ~C 6 Alkenyl, C 3 ~C 6 Haloalkenyl, C 3 ~C 6 Alkynyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 6 ~C 10 Aryl C 1 ~C 3 Alkyl, R 13 C substituted with 1 to 4 groups represented by 6 ~C 10 Aryl C 1 ~C 3 Alkyl, Heteroaryl C 1 ~C 3 Alkyl, and R 13 Heteroaryl C substituted with 1 to 3 groups represented by 1 ~C 3 alkyl; R 10 is hydrogen, C 1 ~C 6 Alkyl and SO 2 R 14 Selected from: R 11 is hydrogen and C 1 ~C 6 alkyl; or R 10 and R 11 together with the nitrogen to which they are attached form a 3- to 6-membered heterocyclyl ring, optionally containing an oxygen atom; R 12 is hydrogen, C 1 ~C 4 Alkyl and C 1 ~C 4 alkylcarbonyl; Each R 13 is halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, cyano, and C 1 ~C 4 independently selected from alkylsulfonyl; R 14 is C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, and C 1 ~C 4 Alkyl (C 1 ~C 4 (alkyl)amino; Each R 15 is hydrogen, halogen, C 1 ~C 4 Alkyl, and C 1 ~C 4 haloalkyl; R 16 is halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, cyano, and C 1 ~C 4 alkylsulfonyl; R 17 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkylsulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkylsulfonylamino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 Selected from: R 18 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkylsulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkylsulfonylamino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 Selected from: R 19 is hydrogen, halogen, cyano, nitro, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Haloalkoxy C 1 ~C 6 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkylsulfonyloxy, C 1 ~C 4 Haloalkylsulfonyloxy, C 1 ~C 4 Alkylthio, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Haloalkylthio, C 1 ~C 4 Haloalkylsulfinyl, C 1 ~C 4 Haloalkylsulfonyl, amino, C 1 ~C 4 Alkylamino, di(C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkylcarbonylamino, C 1 ~C 4 Alkylcarbonyl (C 1 ~C 4 alkyl)amino, C 1 ~C 4 Alkyloxycarbonylamino, aminocarbonylamino, C 1 ~C 4 Alkylaminocarbonylamino, C 1 ~C 4 Alkylsulfonylamino, C 1 ~C 4 Haloalkylsulfonylamino, CO 2 R 9 , and CONR 10 R 11 Selected from: However, R 1 , R 2 , R 17 , R 18 and R 19 are not all hydrogen) or an agriculturally acceptable salt thereof.

2. X 1 is C-R 1 2. The compound of claim 1 ,

3. X 2 The compound according to claim 1 or 2, wherein is nitrogen.

4. X 3 is C-R 18 The compound according to any one of claims 1 to 3,

5. X 4 is C-R 19 The compound according to any one of claims 1 to 4,

6. The compound according to any one of claims 1 to 5, wherein Y is C-H.

7. The compound according to any one of claims 1 to 6, wherein B is O.

8. The compound according to any one of claims 1 to 7, wherein n is 2.

9. R 2 The compound according to any one of claims 1 to 8, wherein is selected from hydrogen, fluorine, chlorine and trifluoromethyl.

10. R 3 The compound according to any one of claims 1 to 9, wherein is selected from hydrogen, chlorine and fluorine.

11. R 4 A compound according to any one of claims 1 to 10, wherein is selected from hydrogen, chlorine, bromine, cyano and aminothiocarbonyl, more preferably chlorine, bromine and cyano.

12. R 8 Is OR 9 The compound according to any one of claims 1 to 11,

13. 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. 13. A method for controlling or preventing the growth of undesired plants, comprising applying a herbicidally effective amount of a compound of formula (I) according to any one of claims 1 to 12 or a composition according to claim 13 to the plant, its part or its habitat.

15. 15. A method for controlling undesirable vegetation in a plant-growing locus, comprising the steps of: a) providing to said locus a plant comprising at least one nucleic acid comprising a nucleotide sequence encoding a PPO polypeptide that is resistant or tolerant to a "protoporphyrinogen oxidase (PPO)-inhibiting herbicide"; and b) applying to said locus an effective amount of said herbicide, wherein said PPO-inhibiting herbicide is a compound according to any one of claims 1 to 14.

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