Phenylsulfonyl ureas, process for their preparation and their use as herbicides and plant growth regulators

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

• in which
• R1 is H, (C1-C6)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, where each of the three last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, unsubstituted and substituted phenyl, unsubstituted and substituted heterocyclyl, unsubstituted and substituted (C3-C6)cycloalkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, [(C1-C4)alkoxy]carbonyl and [(C1-C4)haloalkoxy]carbonyl, or is unsubstituted or substituted (C3-C6)cycloalkyl, substituted or unsubstituted (C3-C6)cycloalkenyl, unsubstituted or substituted phenyl, unsubstituted or substituted heterocyclyl having 3 to 6 ring atoms, where substituted phenyl, substituted heterocyclyl, substituted cycloalkyl or substituted cycloalkenyl carry, as substituents, one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)alkyl, di[(C1-C4)alkoxy](C1-C4)alkyl, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, NR8R9, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, [(C1-C4)alkyl]carbonyl, OH, phenyl, CN and NO2 and
• R2 is a group of the formula R0-Q0- ,
• in which R0 is a hydrogen atom, (C1-C12)alkyl, (C2-C12)alkenyl or (C2-C12)alkynyl, where each the three last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, [(C1-C6)alkoxy]carbonyl, [(C1-C6)haloalkoxy]carbonyl, CONR6R7, SO2NR6R7, CN, OH, SH, (C3-C6)cycloalkyl, NR8R9, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclyl, or
• is (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, phenyl or heterocyclyl, where the four last-mentioned radicals may be unsubstituted or substituted, and in which Q0 is a direct bond or a divalent group of the formula —O— or —N(R#) where R# is a hydrogen atom, an acyl radical or (C1-C12)alkyl, (C2-C12)alkenyl or (C2-C12)alkynyl, where each of the 3 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, CN, OH, (C3-C6)cycloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted heterocyclyl,
• or is unsubstituted or substituted (C3-C6)cycloalkyl, unsubstituted or substituted (C3-C6)cycloalkenyl or unsubstituted or substituted phenyl, and R0 and R# together with the nitrogen atom of the NR#R0 group may form a heterocyclyl radical, having 3 to 6 ring atoms, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)alkoxy, [(C1-C6)alkoxy]carbonyl, (C1-C6)haloalkyl and oxo,
• R3 is a hydrogen atom, (C1-C12)alkyl;
• (C2-C12)alkenyl or (C2-C12)alkynyl, where each of the 3 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, [(C1-C6)alkoxy]carbonyl, [(C1-C6)haloalkoxy]carbonyl, CONR6R7, SO2NR6R7, CN, OH, (C3-C6)cycloalkyl, NR8R9, unsubstituted or substituted phenyl, unsubstituted or substituted heterocyclyl, or is unsubstituted or substituted (C3-C6)cycloalkyl, unsubstituted or substituted (C3-C6)cycloalkenyl, unsubstituted or substituted heterocyclyl, or unsubstituted or substituted phenyl, or
• R2 and R3 together with the nitrogen atom of the NR2R3 group (N1) form a heterocyclyl radical, having 3 to 6 carbon ring atoms, which is unsubstituted or substituted and which one of the carbon atoms is optionally replaced by one heteroatom selected from the group consisting of N, O, and S, by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)alkoxy, [(C1-C6)alkoxy]carbonyl, (C1-C6)haloalkyl and oxo, where the oxo radical is not adjacent to the nitrogen atom (N1), and
• R4 independently of one another are halogen NH2, NO2, NHOH, NO, NH—NH2, N3, CN, (C1-C4)alkyl, (C1-C4)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy, where each of the 6 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C1-C6)alkylthio, (C1-C6)haloalkylthio, (C1-C6)alkylsulfinyl, (C1-C6)haloalkylsulfinyl, (C1C6)alkylsulfonyl, (C1-C6)haloalkylsulfonyl, [(C1-C6)alkoxy]carbonyl, [(C1-C6)haloalkoxy]carbonyl, CONR6R7, SO2NR6R7, CN, OH, (C3-C6)cycloalkyl, NR8R9, unsubstituted or substituted phenyl or unsubstituted or substituted heterocyclyl,
• or
• is unsubstituted or substituted (C3-C6)cycloalkyl, unsubstituted or substituted (C3-C6)cycloalkenyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted phenyl, [(C1-C4)alkyl]carbonyl or [(C1-C4)alkoxy]carbonyl, where each of the two last-mentioned radicals is unsubstituted or substituted in the alkyl moiety by one or more halogen atoms, or is a radical of the formula C(O)—NR′—R″, C(S)—NR′—R″, CR′═N-Q1-R″, S(O)m-Q1-R″″, P(O)n(-Q1-R″″Q2-R″), NR′-Q1-R″ or NR′″—N═CR′—R″, where R′, R″ and R′″ independently of one another are a hydrogen atom, an acyl radical or an unsubstituted or substituted (C1-C10)hydrocarbon radical, R″″ is a carbon-containing acyl radical or an unsubstituted or substituted (C1-C10)hydrocarbon radical, and Q1 and Q2 independently of one another are a direct bond or a divalent group of the formula —O— or —N(R+)—, where R+ is a hydrogen atom, an aryl radical, or an unsubstituted or substituted (C1-C10)hydrocarbon radical, and m=0, 1, 2 or 3, and n=0, 1 or 2, and R′ together with R″, R+ together with R′, R+ together with R″ or R+ together with R″″ may in each case form a heterocyclyl radical having 3 to 6 carbon ring atoms which is unsubstituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)alkoxy, [(C1-C6)alkoxy]carbonyl, (C1-C6)haloalkyl and oxo,
• I is 0, 1 or 2;
• R5 is H or (C1-C4)alkyl which is unsubstituted or substituted,
• R6 and R7 independently of one another are H, (C1-C6)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, unsubstituted or substituted phenyl or unsubstituted or substituted heterocyclyl or
• R6 and R7 together with the nitrogen atom of the NR6R7 group may form a heterocyclyl radical having 5 or 6 carbon atoms which may optionally be replaced by one heteroatom selected from the group consisting of N, O and S and which is unsubstituted or mono- or polysubstituted by radicals selected from the group consisting of (C1-C4)alkyl and oxo, and
• R8 and R9 independently of one another are (C1-C4)alkylcarbonyl, (C1-C4)haloalkylcarbonyl, (C1-C4)alkoxycarbonyl or (C1-C4)alkylsulfonyl or together with the nitrogen atom, of the NR8R9 group may form a heterocyclyl radical having 5 or 6 carbon ring atoms which may be optionally replaced by one additional heteroatom selected from the group consisting of N, O and S and which is unsubstituted or mono- or polysubstituted by radicals selected from the group consisting of (C1-C4)alkyl and oxo, and
• Q is O, S or NR*,
• R* is (C1-C4)alkyl, (C3-C4)alkenyl or (C3-C4)alkynyl, where each of the three last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy and (C1-C4)alkylthio, and
• R* and R1 together with the nitrogen atom of the NR*R1 group may form a heterocyclyl radical which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6))alkyl, (C1-C6)alkoxy, [(C1-C6)alkoxy]carbonyl, (C1-C6)haloalkyl and oxo,
• W is an oxygen atom or a sulfur atom,
• X, Y independently of one another are H, halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, where each of the three last-mentioned radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkoxy and (C1-C4)alkylthio, are mono- or di[(C1-C4)alkyl]amino, (C3-C5)alkenyl, (C3-C5)alkenyloxy, (C3-C5)alkynyl or (C3-C5)alkynyloxy, and where the radicals R1, R2, R3, and R4, including substituents, have up to 20 carbon atoms, and wherein, if not otherwise specified:
• heterocyclyl is a saturated or unsaturated ring having 3 to 7 ring atom or a heteroaromatic ring having 5 or 6 ring atoms, and wherein one of the ring atoms is a heteroatom selected from the group consisting of N, O, or S and the remaining ring atoms are carbon atoms or is a radical selected from the group consisting of pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, oxazolyl, pyrazolyl, and imidazolyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, or morpholinyl;
• substituents for the (C3-C6)cycloalkyl, (C3-C6) cycloalkenyl, phenyl, or heterocyclic rings or the (C1-C10)hydrocarbon radical, unless otherwise specified are 1, 2, or 3 radicals selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, acylamino, NR8R9, mono-, and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkyl and haloalkyl alkenyl, alkynyl, alkenyloxy, alkynyloxy, and phenyl which is optionally substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, [(C1-C4)alkoxy]carbonyl, [(C1-C4)alkyl]carbonyl, NR8R9, phenyl, CN and NO2.