Heterocyclyl-substituted benzoylcyclohexandiones, their preparation, and their use as herbicides

A heterocyclyl-substituted benzoylcyclohexanedione of the formula (I) or its salt

• 476
• in which
• R1 is halogen, (C1-C4)-alkyl, halogen-(C1-C4)-alkyl, (C1-C4)-alkylsulfenyl, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl or nitro;
• R2 is a radical AB(C)q(D)o which is linked to the benzoyl moiety via A;
• AB(C)q(D)o is a bi-, tri- or tetracyclic radical, where
• i) A, B, C and D are in each case a 3- to 8-membered, saturated, partially saturated, unsaturated or aromatic ring containing 1 to 4 hetero atoms selected from the group consisting of oxygen, nitrogen and sulfur,
• j) the rings A, B, C and D are in each case substituted by v substituents selected from the group consisting of R6, halogen, cyano, nitro, hydroxyl, oxo, (C1-C4)-alkyl, halogen-(C1-C4)-alkyl, (C1-C4)-alkoxy, halogen-(C1-C4)-alkoxy and di-(C1-C4)-alkylamino,
• k) two rings A, B, C and D are linked to each other via two joint atoms,
• l) B is not the benzo group when A contains at least one hetero atom;
• R3 is halogen, halogen-(C1-C4)-alkyl, (C1-C4)-alkylsulfenyl, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl or nitro;
• R4 is OR7, (C1-C4)-alkylthio, halogen-(C1-C4)-alkylthio, (C1-C4)-alkenylthio, halogen-(C2-C4)-alkenylthio, (C2-C4)-alkynylthio, halogen-(C2-C4)-alkynylthio, (C2-C4)-alkylsulfinyl, halogen-(C2-C4)-alkylsulfonyl, (C2-C4)-alkenylsulfinyl, halogen-(C2-C4)-alkenylsulfonyl, (C2-C4)-alkenylsulfinyl, halogen-(C2-C4)-alkynylsulfonyl, (C1-C4)-alkylsulfonyl, halogen-(C1-C4)-alkylsulfonyl, (C2-C4)-alkenylsulfonyl, halogen-(C2-C4)-alkenylsulfonyl, (C2-C4)-alkynylsulfonyl, halogen-(C2-C4)-alkynylsulfonyl, cyano, cyanato, thiocyanato, halogen, or is phenylthio which is substituted by v radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, halogen-(C1-C4)-alkyl, halogen-(C1-C4)-alkoxy, cyano and nitro;
• R5 is tetrahydropyranyl-3, tetrahydropyranyl-4, tetrahydrothiopyranyl-3, (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, these being substituted by w methyl groups, or two radicals R5 bonded to directly adjacent carbon atoms form a bond or, together with the carbon atoms to which they are attached, form a 3- to 6-membered ring substituted by w radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-alkylthio and (C1-C4)-alkoxy;
• R6 is straight-chain or branched [C(R8)2]m-(G)p-[C(R8)2]m-R9;
• R7 is hydrogen, (C1-C4)-alkyl, halogen-(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, halogen-(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, halogen-(C1-C4)-alkyl, (C1-C4)-alkoxy, halogen-(C1-C4)-alkoxy, halogen, cyano and nitro;
• R8 is hydrogen, (C1-C4)-alkyl or halogen;
• R9 is OR13, SR13, SOR 3, SO2R13, CO2R14, CONR14R15, N(R14)COR15, N(R14)SO2R15, P(O)R14R15, halogen, cyano, nitro, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl, aryl, 5- or 6-membered heterocyclyl or heteroaryl with in each case one to four hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, it being possible for these five abovementioned radicals to be substituted by v substituents selected from the group consisting of halogen, cyano, formyl, nitro, (C1-C4)-alkyl, halogen-(C1-C4)-alkyl, (C1-C4)-alkoxy, halogen-(C1-C4)-alkoxy, (C1-C4)-alkylthio, halogen-(C1-C4)-alkylthio and R10, or is a radical of the formula Va to Vt:
• 477
• R10 is [(C1-C4)-alkylene-O-(C1-C4)-alkylene]n-O—(C1-C4)-alkyl, or is (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl, each of which is substituted by v halogen atoms.
• R11 is hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C8)-cycloalkyl, aryl, aryl-(C1-C6)-alkyl, heteroaryl, heterocyclyl, halogen-(C1-C4)-alkyl;
• R12 is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C9)-cycloalkyl, aryl, aryl-(C1-C6)-alkyl, heteroaryl, heterocyclyl, halogen-(C1-C4)-alkyl, or, if R11 and R12 are bonded to one atom or to two directly adjacent atoms, they form together with the atoms binding them 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;
• R13 is R7, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl or (C3-C8)-cycloalkyl-(C1-C6)-alkyl;
• R14 and R15 independently of one another are hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkenyloxy, (C2-C6)-alkynyl, halogen-(C1-C6)-alkyl, (C3-C8)-cycloalkyl, cyano-(C1-C6)-alkyl, halogen-(C2-C6)-alkenyl, halogen-(C2-C6)-alkynyl, substituted or unsubstituted aryl or substituted or unsubstituted aryl-(C1-C6)-alkyl;
• G is oxygen or 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 independently of one another are 0, 1 or 2;
• o, p and q independently of one another are 0 or 1;
• V is 0, 1, 2 or 3;
• w is0, 1, 2, 3or4.