Substituted 3-heteroaryl(amino- or oxy)pyrrolidin-2-ones, their preparation and use as herbicides or plant growth regulators

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

• 187
• in which
• A is a radical as defined under (a1) to (a5), where
• (a1) is unsubstituted aryl having 6-18 carbon atoms or unsubstituted heteroaryl or heterocyclyl having from 2 to 14 carbon atoms, at least one ring containing one or more identical or different ring heteroatoms from the group N, O, and S,
• (a2) is a radical as defined under (a1) which is further substituted by one or more fused-on nonaromatic carbocyclic rings having in each case from 4 to 7 ring atoms or heterocyclic rings having in each case from 4 to 7 ring atoms and one or more ring heteroatoms from the group N, O, and S,
• (a3) is a radical as defined under (a1) or (a2) which is further substituted,
• (a4) is (C1-C6)-alkyl, (C3-C9)-cycloalkyl, (C2-C6)-alkenyl, (C5-C9)-cycloalkenyl or (C2-C6)-alkynyl,
• (a5) is one of the hydrocarbon radicals defined under (a4) which further carries one or more identical or different radicals from the group of the radicals of subgroups (a5.1) and (a5.2), where
• subgroup (a5.1) is composed of the radicals halogen, amino, hydroxyl, nitro, cyano, mercapto, carboxyl, carbamoyl, SF5, aminosulfonyl, (C3-C9)-cycloalkyl, (C5-C9)-cycloalkenyl, mono-(C1-C6)-alkylamino, di-((C1-C6)-alkyl)-amino, N-((C1-C6)-alkanoyl)-amino, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C3-C9)-cycloalkoxy, (C5-C9)-cycloalkenyloxy, ((C1-C6)-alkoxy)-carbonyl, (C1-C6)-alkanoyl, (C1-C6)-alkylthio, (C3-C9)-cycloalkylthio, (C2-C6)-alkenylthio, (C5-C9)-cycloalkenylthio, (C2-C6)-alkynylthio, (C1-C6)-alkynylsulfinyl, (C1-C6)-alkylsulfonyl, mono-((C1-C6)-alkyl)-aminosulfonyl, di-((C1-C6)-alkyl)-aminosulfonyl, N-((C1-C6)-alkyl)-aminocarbonyl, N, N-di-((C1-C6)-alkyl)-aminocarbonyl, N-((C1-C6)-alkanoyl)-aminocarbonyl, N-((C1-C6)-alkanoyl)-N-((C1-C6)-alkyl)-aminocarbonyl and, in the case of cyclic radicals, additionally (C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, ((C1-C4)-alkoxy)-carbonyl-(C1-C4)-alkyl, (C1-C4)-alkylthio)-(C1-C4)-alkyl, mono-((C1-C4)-alkyl)-amino-(C1-C4)-alkyl and di-((C1-C4)-alkyl)-amino-(C1-C4)-alkyl, each of the above hydrocarbon substituents (a5.1) being unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio and, in the case of cyclic radicals, additionally (C1-C4)-alkyl and halo-(C1-C4)-alkyl, and
• subgroup (a5.2) is composed of the radicals aryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio, each of the last-mentioned 6 radicals being unsubstituted or substituted by one or more identical or different radicals from the group [=substituent group (a5.2.1)] consisting of halogen, amino, hydroxyl, nitro, cyano, mercapto, carboxyl, carbamoyl, aminosulfonyl, (C1-C4)-alkyl, (C1-C4)-haloalkyl, ((C1-C4)-alkoxy)-(C1-C4)-alkyl, ((C1-C4)-alkoxy)-carbonyl-(C1-C4)-alkyl, ((C1-C4)-alkylthio)-(C1-C4)-alkyl, mono-((C1-C4)-alkyl)-amino-(C1-C4)-alkyl and di-(C1-C4)-alkyl)-amino-(C1-C4)-alkyl, (C2-C6)-cycloalkyl, (C2-C4)-alkenyl, (C5-C9)-cycloalkenyl, (C2-C6)-alkynyl, mono-((C1-C4)-alkyl)-amino, di-((C1-C4)-alkyl)-amino, N-((C1-C6)-alkanoyl)-amino, N-((C1-C6)-alkanoyl)-amino, N-((C1-C6)-alkanoyl)-N-((C1-C4)-alkyl)-amino, (C1-C6)-alkoxy, (C1-C6)-alkoxy-[poly-(C1-C4)-alkylenoxy)]-, hydroxy-[poly-(C1-C4)-alkylenoxy)]—(C3-C6)-cycloalkylenoxy, (C2-C6)-haloalkenyloxy, (C2-C6)-alkynyloxy, (C2-C6)-haloalkynyloxy, ((C1-C4)-alkoxy)-carbonyl, (C1-C6)-alkanoyl, (C1-C4)-alkylthio, (C3-C6)-cycloalkylthio, (C2-C4)-alkenylthio, (C5-C9)-cycloalkenylthio, (C2-C4)-alkynylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, mono-(C1-C4)-alkylaminosulfonyl, di-((C1-C4)-alkyl)-aminosulfonyl, N-((C1-C4)-alkyl)-aminocarbonyl, N,N-di-((C1-C4)-alkyl)-aminocarbonyl, N-((C1-C4)-alkanoyl)-aminocarbonyl and N-((C1-C4)-alkanoyl)-N-((C1-C4)-alkyl)-aminocarbonyl, each of the hydrocarbon substituents from the above substituent subgroup (a5.2.1) being unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, nitro, cyano, thiocyanato, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio and, in the case of cyclic radicals, additionally (C1-C4)-alkyl and halo-(C1-C4)-alkyl,
• B is a direct bond or (C1-C4)-alkylene, (C2-C4)-alkenylene, (C2-C4)-alkynylene, it being possible for individual carbon atoms to have been replaced by nitrogen atoms,
• W is O, S or H2,
• V is a divalent group of the formula CH2, S, O, or CHR3 or CR3R4, where
• R3 is selected from the group consisting of
• (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, mono-(C1-C6)-alkylamino, di-((C1-C6)-alkyl)-amino, N-(C1-C6)-alkanoyl)-amino, (C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C3-C9)-cycloalkoxy, (C5-C9)-cycloalkenyloxy, (C1-C6)-alkylthio, (C3-C9)-cycloalkylthio, (C2-C6)-alkenylthio, (C5-C9)-cycloalkenylthio, (C2-C6)-alkynylthio, (C1-C6)-alkanoyl, (C2-C6)-alkenylcarbonyl, (C2-C6)-alkynylcarbonyl, arylcarbonyl, (C1-C6)-alkoxycarbonyl, (C2-C6)-alkenyloxycarbonyl, (C2-C6)-alkynoxycarbonyl, aryloxycarbonyl, (C1-C6)-alkylsulfinyl and (C1-C6)-alkylsulfonyl, each of the above radicals indicated for R3 being unsubstituted or substituted by halogen or cyano, and
• R4 independently of R3 being one of the radicals defined under R3,
• R1 and R2 independently of one another are each H, amino, (C1-C6)-alkyl, (C2-C6)-alkenylcarbonyl, (C2-C6)-alkynylcarbonyl, mono-(C1-C6)-alkylamino, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C1-C6)-alkanoyl, (C1-C6)-alkenylcarbonyl, (C2-C6)-alkynylcarbonyl, (C1-C6)-alkoxycarbonyl, di-((C1-C6)-alkyl)-amino-(C1-C6)-alkyl, di-((C1-C6)-alkyl)-amino-(C1-C6)-alkenyl, di-((C1-C6)-alkyl)-aminocarbonyl, each of the last-mentioned 14 radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen and cyano,
• Q is a divalent group of the formula O, S, SO, SO2, NR5, CR6R7, CR6OR7, CO, CS or C═N—R′, in which R′ is H or (C1-C4)-alkyl, and in the formulae
• R6 and R7 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-alkenyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl or cyano and R5 is hydrogen, hydroxyl, formyl, NR8R9, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, (C1-C4)-alkyloxy, (C2-C4)-alkenyloxy or (C2-C4)-alkynyloxy, each of the last-mentioned hydrocarbon radicals for R5 being unsubstituted or substituted by one or more substituents from the group consisting of OR8, COR8, COOR8, OCOR8, CN, halogen, S(O)pR8 [where p=0, 1, or 2], NR8R9, NO2, NR8COR9, NR8CONR9R10, CONR8R9 and heterocyclyl, and
• each of the radicals R8, R9 and R10 independently of one another being hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl or (C2-C4)-alkynyl, each of the last-mentioned 3 radicals being unsubstituted or substituted by halogen, and
• D is aryl if Q is selected from the group O, S, SO, SO2 or NR5, or is heteroaryl having 3-5 carbon atoms and 1, 2, or 3 identical or different ring heteroatoms selected from the group N, O, and S, if Q is selected from the group O, S, SO, SO2, NR5, CR6R7, CR6OR7, CO, CS or C═N—R′, the aryl or the heteroaryl being unsubstituted or substituted.