Substituted pyrrolidin-2-ones, salts thereof and their use as herbicidally active substances

A substituted pyrrolidin-2-one of the general formula (I) or salts thereof

• in which
• A1, A2, and A3 are the same or different and independently from one another represent N (nitrogen) or the C—R16 moiety, with a maximum of two adjacent nitrogen atoms, and where R16 in each C—R16 moiety is the same or different as defined below,
• R1 represents hydrogen, (C1-C8)-alkyl, (C1-C10)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkyl, R19—O—(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl,
• R2 and R3 independently of one another represent hydrogen, halogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C10)-haloalkyl, (C3-C10)-cycloalkyl, aryl-(C1-C8)-alkyl, aryl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, R19O—(C1-C8)-alkyl, OR19, R17R18N—(C1-C8)-alkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, C(═O)R19, C(═O)OR19, C(═O)NR17R18, R20S(O)m—(C1-C8)-alkyl,
• R4 represents hydrogen, (C1-C8)-alkyl, (C1-C10)-haloalkyl, cyano-(C1-C8)-alkyl, nitro-(C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-C10)-halocycloalkyl, (C4-C10)-cycloalkenyl, (C4-C10)-halocycloalkenyl, aryl-(C1-C8)-alkyl, R19O—(C1-C8)-alkyl, R19O—(C1-C8)-alkoxy-(C1-C8)-alkyl, R20S(O)m—(C1-C8)-alkyl, R17R18N—(C1-C8)-alkyl, R19O(O)C—(C1-C8)-alkyl, R19(O═)C—(C1-C8)-Alkyl, R17R18N(O)C—(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, aryl, heteroaryl, heterocyclyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, (C1-C8)-alkylthio-(C1-C8)-haloalkyl, tris-[(C1-C8)-alkyl]silyl-(C1-C8)-alkyl,
• R5, R6, R7 and R8 independently of one another represent hydrogen, halogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C10)-haloalkyl, (C3-C10)-cycloalkyl, aryl-(C1-C8)-alkyl, aryl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C5)-alkyl, R19O—(C1-C5)-alkyl, OR19, NR17R18, R17R18N—(C1-C8)-alkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, C(═O)R19, C(═O)OR19, C(═O)NR17R18, S(O)mR20, R20S(O)m—(C1-C8)-alkyl,
• R9 and R10 independently of one another represent hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C10)-haloalkyl, (C3-C10)-cycloalkyl, aryl-(C1-C8)-alkyl, aryl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, R19O—(C1-C8)-alkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, R20S(O)m (C1-C8)-alkyl,
• R11 and R12 independently of one another represent halogen, cyano, nitro, thiocyanato, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C10)-haloalkyl, (C3-C10)-cycloalkyl, aryl-(C1-C8)-alkyl, aryl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, R19O—(C1-C8)-alkyl, cyano-(C1-C8)-alkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, R20S(O)m—(C1-C8)-alkyl, R17R18N—(C1-C8)-alkyl, OR19, NR17R18, S(O)mR20, N—O—R19, C(═N—O—R19)H, C(═O)H, C(═O)R19, C(═O)OR19, C(═O)NR17R18, tris-[(C1-C8)-alkyl]silyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, (C1-C8)-alkylthio-(C1-C8)-haloalkyl,
• m is 0, 1, 2,
• X represents O (oxygen), S (sulfur), NR13, or a group CR14R15,
• R13 represents hydrogen, amino, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C10)-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C10)-cycloalkyl, (C3-C10)-halocycloalkyl, (C4-C10)-cycloalkenyl, (C4-C10)-halocycloalkenyl, R19O—(C1-C8)-alkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, R20S(O)m—(C1-C8)-alkyl, R17R18N—(C1-C8)-alkyl, OR19, NR17R18, S(O)mR20, C(═O)R19, C(═O)OR19, C(═O)NR17R18, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl,
• R14 and R15 are equal or different and independently of one another represent (C1-C8)-alkyl, (C1-C10)-haloalkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(C1-C8)-alkyl, R19—O—(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, C(═O)R19, C(═O)OR19, C(═O)NR17R18, R19O(O)C—(C1-C8)-alkyl, R19(O═)C—(C1-C8)-Alkyl, R17R18N(O)C—(C1-C8)-alkyl, cyano-(C1-C8)-alkyl,
• R4 and R13 together with the nitrogen atom to which they are bonded form a fully saturated or partly saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution.
• R14 and R15 together with the carbon atom to which they are bonded form a fully saturated, or partly saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution.
• R14 and R15 together with the carbon atom to which they are bonded form an unsaturated 5- to 6-membered heteroaromatic or aromatic ring optionally having further substituents.
• R16 represents hydrogen, halogen, cyano, nitro, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C10)-haloalkyl, (C3-C10)-cycloalkyl, aryl-(C1-C8)-alkyl, aryl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, R19O—(C1-C8)-alkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, R20S(O)m—(C1-C8)-alkyl,
• R17R18N—(C1-C8)-alkyl, OR19, NR17R18, S(O)mR20, C(═O)R19, C(═N—O—R9)H, C(═O)H, C(═O)OR19, C(═O)NR17R18, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, (C1-C8)-alkylthio-(C1-C8)-haloalkyl,
• R17 and R18 are equal or different and independently of one another represent hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C10)-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C10)-cycloalkyl, (C3-C10)-halocycloalkyl, (C4-C10)-cycloalkenyl, (C4-C10)-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, (C1-C8)-alkylthio-(C1-C8)-alkyl, (C1-C8)-haloalkylthio-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C10)-cycloalkenyl-(C1-C8)-alkyl, COR19, SO2R20, heterocyclyl, (C1-C8)-alkoxycarbonyl, bis-[(C1-C8)-alkyl]aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkyl-aminocarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkyl-aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(C1-C8)-alkyl, (C2-C8)-alkynyloxycarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl, heteroaryl-(C1-C8)-alkoxycarbonyl, (C2-C8)-alkenyloxycarbonyl, (C2-C8)-alkynyloxycarbonyl, heterocyclyl-(C1-C8)-alkyl, or
• R17 and R18 together with the carbon atom to which they are bonded form a fully saturated or partly saturated 3- to 10-membered monocyclic or bicyclic ring optionally interrupted by heteroatoms and optionally having further substitution,
• R19 represents hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkinyl, (C1-C8)-cyanoalkyl, (C1-C10)-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkinyl, (C3-C10)-cycloalkyl, (C3-C10)-halocycloalkyl, (C4-C10)-cycloalkenyl, (C4-C10)-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, aryl, aryl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxy-(C1-C8)-alkyl, aryloxy-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroaryloxy-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C10)-cycloalkenyl-(C1-C8)-alkyl, bis-[(C1-C8)-alkyl]aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkyl-aminocarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkyl-aminocarbonyl-(C1-C8)-alkyl, bis-[(C1-C8)-alkyl]amino-(C2-C6)-alkyl, (C1-C8)-alkyl-amino-(C2-C6)-alkyl, aryl-(C1-C8)-alkylamino-(C2-C6)-alkyl, R20O)mS—(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkoxy-(C1-C8)-alkyl, heterocyclyloxy-(C1-C8)-alkyl, tris-[(C1-C8)-alkyl]silyl-(C1-C8)-alkyl, bis-[(C1-C8)-alkyl](aryl)silyl(C1-C8)-alkyl, [(C1-C8)-alkyl]-bis-(aryl)silyl-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkyl, (C3-C8)-cycloalkylcarbonyloxy-(C1-C8)-alkyl, arylcarbonyloxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkyl, Heterocyclylcarbonyloxy-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(C1-C8)-alkyl, (C2-C8)-alkynyloxycarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, and
• R20 represents hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C10)-haloalkyl, (C2-C8)-haloalkenyl, (C3-C8)-haloalkynyl, (C3-C10)-cycloalkyl, (C3-C10)-halocycloalkyl, (C4-C10)-cycloalkenyl, (C4-C10)-halocycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C10)-cycloalkenyl-(C1-C8)-alkyl, bis-[(C1-C8)-alkyl]amino, (C1-C8)-alkyl-amino, aryl-(C1-C8)-amino, aryl-(C1-C6)-alkyl-amino, aryl-[(C1-C8)-alkyl]amino;
• heteroaryl-(C1-C8)-amino, heteroaryl-(C1-C6)-alkyl-amino, heteroaryl-[(C1-C8)-alkyl]amino;
• Hetercyclyl-(C1-C8)-amino, heterocyclyl-(C1-C6)-alkyl-amino, heterocyclyl-[(C1-C8)-alkyl]amino;
• (C3-C8)-cycloalkyl-amino, (C3-C8)-cycloalkyl-[(C1-C8)-alkyl]amino;
• N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl.