Herbicidally active benzoylcyclohexanediones

A compound of the formula (I) or a salt thereof

• 290
• in which
• X1 is a divalent unit selected from the group consisting of O, S(O)n, NH, N[Lp—R3];
• X2 is a straight-chain or branched (C1-C6)-alkylene, (C2-C6)-alkenylene or (C2-C6)-alkynylene chain which is substituted by w halogen atoms and by k radicals [Lp—R3];
• C1(C2)q(C3)o is a mono-, bi- or tricyclic radical, where
• e) the rings C1, C2 and C3 are in each case a 3- to 8-membered, saturated or partially saturated ring selected from the group consisting of cycloalkyl, cycloalkenyl, oxiranyl and oxetanyl,
• f) the rings C1, C2 and C3 are in each case linked to each other via one or two joint atoms;
• R1 and R2 independently of one another are hydrogen, mercapto, nitro, cyano, halogen, thiocyanato, (C1-C6)-alkyl—CO—O, (C1-C6)-alkyl-S(O)n—O, (C1-C6)-alkyl—S(O)n, di-(C1-C6)-alkyl—NH—SO2, (C1-C6)-alkyl-SO2—NH, (C1-C6)-alkyl—NH—CO, (C1-C6)-alkyl-SO2-[(C1-C6)-alkyl]amino, (C1-C6)-alkyl-CO-((C1-C6)-alkyl)amino, 1,2,4-triazol-1-yl, (C1-C6)-alkyl—O—CH2, (C1-C6)-alkyl-S(O)n—CH2, (C1-C6)-alkyl—NH—CH2, [(C1-C6)-alkyl]2N—CH2, 1,2,4-triazol-1-yl-CH2, or are (C1-C6)-alkyl-(D)p, (C2-C6)-alkenyl-(D)p, (C2-C6)-alkynyl-(D)p, (C3-C9)-cycloalkyl-(D)p, (C3-C9)-cycloalkenyl-(D)p, (C1-C6)-alkyl-(C3-C9)-cycloalkyl-(D)p or (C1-C6)-alkyl-(C3-C9)-cycloalkenyl-(D)p, each of which is substituted by v radicals selected from the group consisting of cyano, nitro and halogen;
• R3 is hydrogen, hydroxyl, halogen, mercapto, amino, nitro, a carbon-containing radical or, if p in X1 is zero, R3 is oxo, NR8, N—OR8 or N—NR8R9;
• D is oxygen or sulfur;
• L is in each case straight-chain or branched Ap—[C(R6)2]w—[Ap—C(R6)2]x—Ap or Ap—M—Ap;
• with the proviso that 2 or 3 of the variable terms p, w and x shall not simultaneously be zero;
• A is a divalent unit selected from the group consisting of O, S(O)n, NH, N-(C1-C6)-alkyl, N-(C2-C6)-alkenyl and N-(C2-C6)-alkynyl;
• M is (C1-C6)-alkylene, (C2-C6)-alkenylene or (C2-C6)-alkynylene, each of which is substituted by w radicals R6;
• R4 is OR7, (C1-C4)-alkylthio, halo-(C1-C4)-alkylthio, (C1-C4)-alkenylthio, halo-(C2-C4)-alkenylthio, (C2-C4)-alkynylthio, halo-(C2-C4)-alkynylthio, (C2-C4)-alkylsulfinyl, halo-(C2-C4)-alkylsulfinyl, (C2-C4)-alkenylsulfinyl, halo-(C2-C4)-alkenylsulfinyl, (C2-C4)-alkynylsulfinyl, halo-(C2-C4)-alkynylsulfinyl, (C1-C4)-alkylsulfonyl, halo-(C1-C4)-alkylsulfonyl, (C2-C4)-alkenylsulfonyl, halo-(C2-C4)-alkenylsulfonyl, (C2-C4)-alkynylsulfonyl, halo-(C2-C4)-alkynylsulfonyl, cyano, cyanato, thiocyanato, halogen or phenylthio;
• R5 is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl, (C1-C4)-alkyl, (C3-C8)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-alkylcarbonyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylthio, phenyl, the eight last-mentioned groups being substituted by v radicals selected from the group consisting of halogen, (C1-C4)-alkylthio and (C1-C4)-alkoxy, or
• two radicals R5 bonded to a joint carbon atom form a chain selected from the group consisting of OCH2CH2O, OCH2CH2CH2O, SCH2CH2S and SCH2CH2CH2S, this group being substituted by w methyl groups, or
• two radicals R5 bonded to directly adjacent carbon atoms, together with the carbon atoms to which they are attached, form a 3- to 6-membered ring which is substituted by w radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkylthio and (C1-C4)-alkoxy;
• R6 is (C1-C4)-alkyl, halogen, cyano or nitro;
• R7 is hydrogen, (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, formyl, (C1-C4)-alkylcarbonyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylaminocarbonyl, di-(C1-C4)-alkylaminocarbonyl, (C1-C4)-alkylsulfonyl, halo-(C1-C4)-alkylsulfonyl, benzoyl or phenylsulfonyl, the two last-mentioned groups being substituted by v radicals selected from the group consisting of (C1-C4)-alkyl, halo-(C1-C4)-alkyl, (C1-C4)-alkoxy, halo-(C1-C4)-alkoxy, halogen, cyano and nitro;
• R8 is hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C8)-cycloalkyl, aryl, aryl-(C1-C6)-alkyl, heteroaryl, heterocyclyl, halo-(C1-C4)-alkyl;
• R9 is hydrogen, (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 R8 and R9 are bonded to one atom or to two directly adjacent atoms, they together with the atoms to which they are bonded form a saturated, partially or fully unsaturated five- to six-membered ring which contains p hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur;
• Y is a divalent unit selected from the group consisting of O, S, N—H, N-(C1-C4)-alkyl, CHR5 and C(R5)2;
• Z is a divalent unit selected from the group consisting of O, S, SO, SO2, N—H, N-(C1-C4)-alkyl, CHR5 and C(R5)2;
• m and n are each 0, 1 or 2;
• o, p and q are each o or 1;
• w and x are each 0, 1, 2, 3 or 4;
• v is 0, 1, 2 or 3.