Phenylsulfonylureas, processes for their preparation, and their use as herbicides and plant growth regulators

A compound of the formula (1) or a salt thereof

• in which
• R1 is an acyl radical of the formula S(O)n—R10 or CO—Q—R11,
• R2, R3, R4, R5 are identical or different radicals selected from the group consisting of H, (1-6)alkyl, (1-4)alkoxy, (1-4)haloalkyl, (1-4)haloalkoxy and halogen,
• R6 is H, OH, formyl, a radical of the formula R, R—O—, R—CO, R—O—CO—, R—SO2—, R—SO— or RR0NSO2—, in which each of the radicals R and R0 is a hydrocarbon radical which is unsubstituted or substituted, and,
• R7 is CHO, [(1-6)alkyl]carbonyl, [(2-6)alkenyl]carbonyl, [(2-6)alkynyl]carbonyl, (1-6)alkylsulfonyl, (2-6)alkenylsulfonyl, (2-6)alkynylsulfonyl, [(3-6)cycloalkyl]carbonyl, [(5-6)cycloalkenyl]carbonyl, [(3-6)cycloalkyl]-sulfonyl, (5-6)cycloalkenylsulfonyl, each of the 10 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio, (1-4)alkyl sulfonyl, (1-4)alkylsulfinyl, (1-4)alkylcarbonyl, [(1-4)alkoxy]carbonyl, [(1-4)alkyl]carbonyloxy and CN and, in the case of cyclic radicals, also by (1-4)alkyl and (1-4)haloalkyl, or
• phenylcarbonyl or phenylsulfonyl, each of the two last-mentioned radicals being unsubstituted or substituted in the phenyl ring by one or more radicals selected from the group consisting of halogen, CN, NO2, (1-4)alkyl, (1-4)haloalkyl, (1-4)alkoxy and (1-4)haloalkoxy, or
• mono- or di[(1-4)alkyl]aminosulfonyl which is unsubstituted or substituted in the alkyl moiety by one or more radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio, (1-4)alkylsulfinyl, (1-4)alkylsulfonyl, [(1-4)alkyl]carbonyl, [(1-4)alkyl]carbonyloxy, [(1-4)alkoxy]carbonyl and CN, or a group of the formula COCOR′ in which R′=H, OH, (1-4)alkoxy or (1-4)alkyl, or a group of the formula
• or
• NR6R7 together are a chain of the formula —(CH2)m1B1 of —B1—(CH2)m2—B2—, where m1 is 3, 4 or 5 and m2 is 2, 3 or 4
• B1 is SO2 or CO,
• B2 is SO2 or CO
• W is an oxygen or sulfur atom,
• Wo is O or S,
• T0 is O or S,
• R8 is H, (1-6)alkyl, (2-6)alkenyl, (1-6)alkoxy, (1-4)alkylthio, [(1-4)alkyl]-carbonyl or [(1-4)alkoxy]carbonyl, each of the six last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio and CN, or is halogen, NO2, CN, NH2 or mono- or disubstituted amino,
• R9 is H or (1-6)alkyl,
• R10 is NH2, mono- or disubstituted amino or a hydrocarbon radical which is unsubstituted or substituted, and which,
• n is the number 0, 1 or 2, with the exception of the case R10=NH2 or mono- or disubstituted amino, in which case n=2,
• R11 is H or a hydrocarbon radical which is unsubstituted or substituted, or is a heterocycle wherein said heterocycle is an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 to 6 ring atoms, wherein 1 of the ring atoms is a heteroatom selected from the group consisting of N, O, and S, or is pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, oxazol, pyrazolyl, imidazol, piperidinyl, piperazinyl, dioxolanyl, or morpholinyl, wherein said groups are unsubstituted or substituted, and,
• R12 is (1-4)alkyl, (3-4)alkenyl or (3-4)alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio, [(1-4)alkyl]carbonyl and [(1-4)alkoxy]carbonyl,
• R13, R14 independently of one another are H, (1-4)alkyl, (3-4)alkenyl or (3-4)alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted by one or more of the radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio, [(1-4)alkyl]carbonyl and [(1-4)alkoxy]carbonyl,
• the radicals R15 together with the nitrogen atom are a heterocyclic ring which has 5 or 6 ring members, may contain one further hetero atom selected from the group consisting of N, O and S at the oxidation levels which are possible and which is unsubstituted or substituted by (1-4)alkyl or the oxo group, or which is benzo-fused,
• Q is an oxygen or sulfur atom or a group of the formula —NR′— in which R′ is H or a hydrocarbon radical which is unsubstituted or substituted, or is an acyl radical,
• A is a radical of the formula
• one of the radicals X and Y is hydrogen, halogen, (1-3)alkyl or (1-3)alkoxy, each of the two last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-3)alkoxy and (1-3)alkylthio, and the other of the radicals X and Y is hydrogen, halogen, (1-3)alkyl, (1-3)alkoxy or (1-3)alkylthio, each of the three last-mentioned alkyl containing radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-3)alkoxy and (1-3)alkylthio, or is a radical of the formula NRaRb, (3-6)cycloalkyl, (2-4)alkenyl, (2-4)alkynyl, (3-4)alkenyloxy or (3-4)alkynyloxy,
• Z is CH,
• Ra and Rb independently of one another are H, (1-4)alkyl or (2-4)alkenyl,
• wherein the hydrocarbon radical is defined as alkyl, alkenyl, alkynyl or aryl having up to 12 carbon atoms, and when substituted, the substituents are halogen, (1-4)alkoxy, (1-4)haloalkoxy, (1-4)alkylthio, hydroxy, amino, nitro, (1-4)carboxy, cyano, azido, [(1-4)alkoxy]carbonyl, [(1-4)alkyl]carbonyl, formyl, carbamoyl, mono(1-4)alkylaminocarbonyl, di(1-4)alkylaminocarbonyl, acylamino, mono(1-4)alkylamino, (1-4)alkylsulfinyl, (1-4)haloalkylsulfinyl, (1-4)alkylsulfonyl, (1-4)haloalkylsulfonyl, (2-4)alkenyl, (2-4)alkynyl, (2-4)alkenyloxy, (2-4)alkynyloxy, mono- or disubstituted amino, unsubstituted or N-substituted hydroxylamino, or unsubstituted or N-substituted hydrazino, wherein the substitution on the last 4 mentioned substituted radicals are selected from the groups consisting of (1-4)alkyl, (1-4)alkoxy, (1-4)acyl, and (6-12)aryl,
• wherein the substituents on the aryl or heterocyclic groups are those identified above for the hydrocarbon radical or when an aliphatic heterocycle radical are also oxo, and
• wherein the substitutents on the mono- and di-substituted amino radicals are selected from the group consisting of (1-4)alkyl, (1-4)alkoxy, (1-4)acyl and (6-12)aryl.