Patent ID: 6448201
Filing Date: 2002-09-10
Classification: C07D

Abstract:
A benzoyl compound of the formula (I) in whichQ is a radical of the formula (Q1) which is linked in the 2-position X is a straight-chain or branched (C1-C6)-alkylene, (C2-C6)-alkenylene or (C2-C6)-alkynylene chain, which is substituted by w radicals selected from the group consisting of OR3a, OCOR3a, (C1-C6)alkyl, (C2-C6)alkenyl (C2-C6)alkynyl, phenyl and phenyl-(C1-C6)-alkyl, and which is interrupted by a hetero atom selected from the group consisting of oxygen and sulfur or which has this hetero atom attached to one of its chain ends, the abovementioned alkyl, alkenyl, alkynyl and phenyl radicals optionally being substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, (C1-C4)-alkylamino, (C1-C4)-dialkylamino, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, (C1-C4)-alkoxycarbonyloxy, (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkylthio, halo-(C1-C4)-alkylthio, (C1-C4)-alkoxy, halo-(C1-C4)-alkoxy; Het is heterocydyl or heteroaryl containing, as ring atom, at least one nitrogen atom and optionally additionally one, two or three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, R1 and R2 independently of one another are hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, OS(O)nR10, (C1-C6)-alkyl-A, (C2-C6)-alkenyl-A, (C2-C6)-alkynyl-A, (C1-C6)-alkoxy-(C1-C6)-alkyl-A, or are (C2-C6)-alkenyloxy-(C1-C6)-alkyl-(A)p, (C2-C6)-alkynyloxy-(C1-C6)-alkyl-(A)p, (C3-C9)-cycloalkyl-(A)p, (C3-C9)-cycloalkenyl-(A)p, (C1-C6)-alkyl-(C3-C9)-cycloalkyl-(A)p, (C1-C6)-alkyl-(C3-C9)-cycloalkyl-(C1-C6)-alkyl-(A)p, (C1-C6)-alkyl-(C3-C9)-cycloalkenyl-(A)p, (C1-C6)-alkyl-(C3-C9)-cycloalkenyl-(C1-C6)-alkyl-(A)p, (C2-C6)-alkenyl-(C3-C9)-cycloalkyl-(A)p, (C2-C6)-alkenyl-(C3-C9)-cycloalkyl-(C1-C6)-alkyl-(A)p, (C2-C6)-alkenyl-(C3-C9)-cycloalkenyl-(A)p, (C2-C6)-alkenyl-(C3-C9)-cycloalkenyl-(C1-C6)-alkyl-(A)p, (C2-C6)-alkynyl-(C3-C9)-cycloalkyl-(A)p, (C2-C6)-alkynyl-(C3-C9)-cycloalkyl-(C1-C6)-alkyl-(A)p, (C2-C6)-alkynyl-(C3-C9)-cycloalkyenyl-(A)p, (C2-C6)-alkynyl-(C3-C6)-cycloalkenyl-(C1-C6)-alkyl-(A)p, OR10, OCOR10, S(O)nR10, SO2N(R10)2, NR10SO2R10 or NR10COR10, each of which is substituted by m radicals selected from the group consisting of cyano and nitro and w radicals selected from the halogen group; R3 is hydrogen, hydroxyl, halogen, mercapto, amino, cyano, nitro, formyl, or is (C1-C4)-alkylamino, (C1-C4)-dialkylamino, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, (C1-C4)-alkylcarbonyloxy, (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkylthio, halo-(C1-C4)-alkylthio, (C1-C4)-alkoxy or halo-(C1-C4)-alkoxy, each of which is substituted by m radicals selected from the group consisting of cyano, nitro, formyl, (C1-C4)-alkylamino, (C1-C4)-dialkylamino, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, (C1-C4)-alkylcarbonyloxy, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, halo-(C1-C4)-alkyl, (C2-C4)-haloalkenyl, (C2-C4)-haloalkynyl, (C1-C4)-alkylthio, halo-(C1-C4)-alkylthio, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy; R3a is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl, phenyl-(C1-C6)-alkyl, it being possible for the five last-mentioned radicals to be substituted in their nonaromatic moiety by w radicals selected from the group consisting of hydroxy, halogen, mercapto, amino, cyano, nitro, formyl, (C1-C4)-alkylamino, (C1-C4)-dialkylamino, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, halo-(C1-C4)-alkyl, (C1-C4)-alkylthio, halo-(C1-C4)-alkylthio, (C1-C4)-alkoxy and halo(C1-C4)-alkoxy; R4 is straight-chain or branched [C(R11)2]m-(A)p-[C(R11)2]m-R12; A is oxygen or sulfur, R5 is OR16, (C1-C6)-alkylthio, halo-(C1-C6)-alkylthio, (C2-C6)-alkenylthio, halo-(C2-C6)-alkenylthio, (C2-C6)-alkynylthio, halo-(C2-C6)-alkynylthio, (C1-C6)-alkylsulfinyl, halo-(C1-C6)-alkylsulfinyl, (C2-C6)-alkenylsulfinyl, halo-(C2C6)-alkenylsulfinyl, (C2-C6)-alkynylsulfinyl, halo-(C2-C6)-alkynylsulfinyl, (C1-C6)-alkylsulfonyl, halo-(C1-C6)-alkylsulfonyl, (C2-C6)-alkenylsulfonyl, halo-(C2-C6)-alkenylsulfonyl, (C2-C6)-alkynylsulfonyl, halo-(C2-C6)-alkynylsulfonyl, cyano, cyanato, thiocyanato or halogen; R6 is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl, or is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C1-C6)-alkylcarbonyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylthio or phenyl, each of which is substituted by w radicals selected from the group consisting of halogen, (C1-C6)-alkylthio and (C1-C6)-alkoxy, or two radicals R6 bound to a joint carbon atom form a chain selected from the group consisting of OCH2CH2O, OCH2CH2CH2O, SCH2CH2S and SCH2CH2CH2S which is optionally substituted by one to four methyl groups; R7 is hydrogen, (C1-C6)-alkyl or (C1-C6)-haloalkyl; R8 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl, or is phenyl which is optionally substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy; R9 is hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkylcarbonyl, halo-(C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylsufonyl, halo-(C1-C6)-alkylsulfonyl, or is benzoyl, benzoylmethyl, phenoxycarbonyl or phenylsulfonyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy and halo-(C1-C4)-alkoxy; R10 is hydrogen, or is (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl or phenyl-(C1-C6)-alkyl, each of which is substituted by w radicals selected from the group consisting of hydroxyl, halogen, mercapto, amino, cyano, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylthio, di-(C1-C4)-alkylamino, (C1-C4)-alkoxyimino, (C1-C4)-alkoxythiocarbonyl, (C1-C4)-alkylcarbonyl-(C1-C4)-alkylamino, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylthiocarbonyl, di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-alkyliminooxy, (C1-C4)-alkoxyamino, (C1-C4)-alkylcarbonyl, (C1-C4)-alkoxy-(C2-C6)-alkoxycarbonyl, (C1-C4)-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, heteroaryl, phenoxy, benzyloxy and heteroaryloxy; R11 is hydrogen, (C1-C4)-alkyl or halogen; R12 is cycloalkyl, cycloalkenyl, aryl, a heterocyclyl or heteroaryl containing one to four hetero atoms selected from the group consisting of oxygen, nitrogen, and sulfur, each of which is substituted by w radicals selected from the group consisting of halogen, cyano, formyl, nitro, (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkoxy, (C1-C4)-alkylthio, halo-(C1-C4)-alkylthio and R13, or is a radical of the formula (Va) to (Vt): R13 is [(C1-C4)-alkylene-Oâ€”(C1-C4)-alkylene]o-Oâ€”(C1-C4)-alkyl, or is (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl, each of which is substituted by w halogen atoms; R14 is hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C9)-cycloalkyl, aryl, aryl-(C1-C6)-alkyl, heteroaryl, heterocydyl, halo-(C1-C4)-alkyl; R15 is hydrogen, tetrahydrofuran-2-yl, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C9)-cycloalkyl, aryl, aryl-(C1-C6)-alkyl, heteroaryl, heterocyclyl, halo-(C1-C4)-alkyl, or, if R14 and R15 are bound to one atom or to two directly adjacent atoms, they form together with the atoms binding them a saturated or partially or fully unsaturated five- to six-membered ring which optionally additionally contains a hetero atom selected from the group consisting of oxygen, nitrogen and sulfur; R16 is hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy(C1-C6)-alkyl, formyl, (C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylaminocarbonyl, di-(C1-C6)-alkylaminocarbonyl, (C1-C6)-alkylsulfonyl, halo-(C1-C6)-alkylsulfonyl, benzoyl or phenylsulfonyl, the two last-mentioned groups being substituted by w identical or different radicals selected from the group consisting of (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, halogen, cyano and nitro; Y is a divalent unit selected from the group consisting of O, S, Nâ€”H, Nâ€”(C1-C6)-alkyl, CHR6 and C(R6)2; Z is a direct bond or a divalent unit selected from the group consisting of O, S, SO, SO2, Nâ€”H, Nâ€”(C1-C6)-alkyl, CHR7 or C(R7)2; k in the event that Het is a bicyclic heteroaromatic ring or heterocycle, is 0, 1 or 2, and in the event that Het is a monocyclic heteroaromatic ring or heterocycle, 1 or 2; m is 0, 1 or 2; n is 0, 1 or 2; o is 1, 2, 3 or 4; p is 0 or 1; v is 1 or 2; w is 0, 1, 2, 3 or 4, or an agriculturally useful salt thereof.