3-aminocarbonyl/3-aminothiocarbonyl-substituted 2-benzoyl-cyclohexan-1,3-diones with herbicidal effect

A 2-benzoylcyclohexane-1,3-dione of formula I

• where the variables have the following meanings:
• R1, R2 are hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, —OR5, —OCOR6, —OSO2R6, —SH, —S(O)nR7, —SO2OR5, —SO2NR5R8, —NR8SO2R6 or —NR8COR6;
• R3 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, —COR9, —CO2R9, —COSR9 or —CONR8R9, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals and for R9 of the radicals —COR9, —CO2R9, —COSR9 and —CONR8R9 to be partially or fully halogenated and/or to have attached to them one to three of the following groups:
• hydroxyl, mercapto, amino, cyano, R10, —OR10, —SR10, —NR8R10, ═NOR10, —OCOR10, —SCOR10, —NR8COR10, —CO2R10, —COSR10, —CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, phenyl-C1-C4-alkyl, hetaryl, phenoxy, phenyl-C1-C4-alkoxy and hetaryloxy, it being possible for the eight last-mentioned radicals, in turn, to be substituted;
• X is oxygen or sulfur;
• z is oxygen or NR8;
• m is 0 or 1;
• n is 0, 1 or 2;
• R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• R6 is C1-C6-alkyl or C1-C6-haloalkyl;
• R7 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• R8 is hydrogen or C1-C6-alkyl;
• R9 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl;
• R10 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• Q is a cyclohexane-1,3-dione ring of formula II
• wherein
• R11, R12, R14 and R16 are hydrogen or C1-C4-alkyl;
• R13 is hydrogen, C1-C4-alkyl or C3-C4-cycloalkyl, it being possible for the two last-mentioned groups to have attached to them one to three of the following substituents:
• halogen, C1-C4-alkylthio or C1-C4-alkoxy;
• or
• is tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahy-dropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothio-pyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,4-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-di-thian-2-yl, it being possible for the 6 last-mentioned radicals to be substituted by one to three C1-C4-alkyl radicals;
• R15 is hydrogen, C1-C4-alkyl or C1-C6-alkoxycarbonyl;
• or R13 and R16 together form a π bond or a three to six-membered carbocyclic ring;
• or
• the CR13R14 unit represents a C═O group;
• where m is 1 if R3 is hydrogen;
• or an agriculturally useful salt thereof.