Substituted pyrazolinyl derivatives, processes for their preparation and their use as herbicides and/or plant growth regulators

Compound of formula (I) and/or a salt thereof,

• in which
• X represents oxygen or sulfur,
• A represents the grouping C—R1 or the grouping N—R9, where R1 in the grouping C—R1 and R9 in the grouping N—R9 each have the meanings according to the definition below and where, if A represents the grouping C—R1, the adjacent grouping C—R2 is attached via a double bond and where, if A represents the grouping N—R9, the adjacent grouping CHR2 is attached via a single bond,
• R1 represents hydrogen, halogen, hydroxy, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-hydroxyalkyl, (C1-C8)-alkoxy, (C1-C8)-alkoxyalkyl, (C1-C8)-alkoxy-(C1-C8)-alkyloxy, (C1-C8)-alkylthio, (C1-C8)-haloalkoxy, (C1-C8)-haloalkylthio, (C3-C10)-cycloalkyl, aryl, heteroaryl, (C3-C8) cycloalkyl-(C1-C8)-alkyl, heterocyclyl, (C2-C8)-alkenyl, (C2-C8)-alkenyloxy, (C2-C8)-alkynyl, (C2-C8)-alkynyloxy, NR10R11, aryl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl or heterocyclyl-(C1-C8)-alkyl,
• R2 represents hydrogen, halogen, hydroxy, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-hydroxyalkyl, hydroxycarbonyl-(C1-C8)-alkyl, (C1-C8)-alkoxy, (C1-C8)-alkoxyalkyl, (C1-C8)-alkoxy-(C1-C8)-alkyloxy, (C1-C8)-alkylthio, (C1-C8)-haloalkoxy, (C1-C8)-haloalkylthio, (C3-C10)-cycloalkyl, aryl, heteroaryl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, heterocyclyl, (C2-C8)-alkenyl, (C2-C8)-alkenyloxy, (C2-C8)-alkynyl, (C2-C8)-alkynyloxy, NR10R11, aryl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, (C1-C8)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10R11, SO2R13, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, aryloxycarbonyl-(C1-C8)-alkyl, arylcarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyl-(C1-C8)-alkyl, heteroarylcarbonyl-(C1-C8)-alkyl or heterocyclylcarbonyl-(C1-C8)-alkyl,
• or where R1 and R2 together with the two carbon atoms to which they are attached form a fully saturated or partially saturated ring which has 3 to 7 members in total, which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and which is optionally substituted further,
• R3 represents hydroxy, hydrothio, halogen, NR10R11, (C1-C8)-alkoxy, (C3-C10)-cycloalkyl-(C1-C8)-alkoxy, aryl-(C1-C8)-alkoxy, (C1-C8)-alkoxy-(C1-C8)-alkoxy, arylcarbonyloxy, (C1-C8)-alkylcarbonyloxy, aryl-(C1-C8)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C3-C10)-cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (C1-C8)-haloalkyl-carbonyloxy, (C2-C8)-alkenylcarbonyloxy, OC(O)OR12, OC(O)SR12, OC(S)OR12, OC(S)SR12, OC(O)NR10R11, OC(S)NR10R11, OSO2R13, OSO2OR12 or OCHO,
• R4 represents hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C10)-cycloalkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkenyl, (C2-C8) haloalkynyl, (C4-C10)-cycloalkenyl, aryl-(C2-C8)-alkenyl, heteroaryl-(C2-C8)-alkenyl, heterocyclyl-(C2-C8)-alkenyl, arylcarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyl-(C1-C8)-alkyl, heteroarylcarbonyl-(C1-C8)-alkyl, (C3-C10)-cycloalkylcarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, C(O)R12, SO2R13, CHO, R10R11N—(C1-C8)-alkyl or cyano-(C1-C8)-alkyl,
• R5 represents hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C10)-cycloalkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, cyano, C(O)OR12, C(O)NR10R11, R12O(O)C—(C1-C8)-alkyl, R12O—(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkyl, (C3-C10)-cycloalkylcarbonyloxy-(C1-C8)-alkyl, arylcarbonyloxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkyl or heterocyclylcarbonyloxy-(C1-C8)-alkyl,
• R6 represents hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C10)-cycloalkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, aryl, heteroaryl, heterocyclyl, aryl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl or heterocyclyl-(C1-C8)-alkyl,
• R7 and R8 are identical or different and independently of one another represent hydrogen, halogen or (C1-C8)-alkyl,
• R9 represents hydrogen, hydroxy, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-hydroxyalkyl, hydroxycarbonyl-(C1-C8)-alkyl, (C1-C8)-alkoxy, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxyalkyloxy, (C1-C8)-haloalkoxy, (C3—C o)-cycloalkyl, aryl, heteroaryl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, heterocyclyl, (C2-C8)-alkenyl, (C2-C8)-alkenyloxy, (C2-C8)-alkynyl, (C2-C8)-alkynyloxy, NR10R11, aryl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, (C1—C8)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10R11, SO2R13, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, aryloxycarbonyl-(C1-C8)-alkyl, arylcarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyl-(C1-C8)-alkyl, heteroarylcarbonyl-(C1-C8)-alkyl or heterocyclylcarbonyl-(C1-C8)-alkyl,
• or where R2 and R9 together with the nitrogen atom or carbon atom to which they are respectively attached form a fully saturated or partially saturated ring which has 3 to 7 members in total, which is optionally interrupted by one to three heteroatoms from the group consisting of N, O and S and which is optionally substituted further,
• R10 and R11 are identical 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, (C2-C8)-haloalkynyl, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, (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-C10)-cycloalkyl-(C1-C8)-alkyl, (C4-C10)-cycloalkenyl-(C1-C8)-alkyl, C(O)R12, SO2R13, heterocyclyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl, aryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl, heteroaryl-(C1-C8)-alkoxycarbonyl, (C2-C8)-alkenyloxycarbonyl, (C2-C8)-alkynyloxycarbonyl or heterocyclyl-(C1-C8)-alkyl,
• R12 represents (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C10)-haloalkyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, (C4-C10)-cycloalkenyl-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, heterocyclyl or heterocyclyl-(C1-C8)-alkyl,
• R13 represents (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C10)-haloalkyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, (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-C10)-cycloalkyl-(C1-C8)-alkyl, (C4-C10)-cycloalkenyl-(C1-C8)-alkyl or NR10R11,
• R14 represents hydrogen or (C1-C8)-alkyl,
• or where R3 and R14 together with the carbon atom to which they are attached form a carbonyl group,
• where the cyclic structural elements of the radicals mentioned respectively in R1, R2, R3, R4, R5, R6, R9, R10, R11, R12 and R13 and the rings formed by R1 and R2 or R2 and R9, having 3 to 7 members in total, are in each case unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, hydroxy, cyano, NR10R11, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylsulfoxy, (C1-C4)-alkylsulfone, (C1-C4)-haloalkylthio, (C1-C4)-haloalkylsulfoxy, (C1-C4)-haloalkylsulfone, (C1-C4)-alkoxy-carbonyl, (C1-C4)-haloalkoxy-carbonyl, (C1-C4)-alkylcarboxy, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C4)-alkoxy-carbonyl-(C1-C4)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(C1-C4)-alkyl, R10R11N-carbonyl, and where the structural elements cycloalkyl, cycloalkenyl and heterocyclyl have n oxo groups, where n=0, 1 or 2.