Substituted n-heterocyclyl- and n-heteroaryl-tetrahydropyrimidinones and the salts thereof, and the use of same as herbicidal active substances

A substituted N-heterocyclyl- or N-heteroaryltetrahydropyrimidinone of formula (I) and/or a salt thereof

• in which
• Q represents the groups Q-1 to Q-30
• where the arrow represents a bond of the respective Q group to the nitrogen of the tetrahydropyrimidinone in formula (I),
• A1, A2, A3, A4 are identical or different and independently of one another represent N (nitrogen) or the moiety C—R8, but there are never more than two adjacent nitrogen atoms, and where R8 in the moiety C—R8 in each case has identical or different meanings according to the definition below, or
• A1 and A2, when each is a group C—R8, together with the atoms to which they are attached form a fully saturated, partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally has further substitution, or
• A2 and A3, when each is a group C—R8, together with the atoms to which they are attached form a fully saturated, partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally has further substitution, or
• A3 and A4, when each is a group C—R8, together with the atoms to which they are attached form a fully saturated, partially saturated or fully unsaturated 5- to 7-membered ring which is optionally interrupted by heteroatoms from the group consisting of N, O and S and optionally has further substitution,
• R1 represents hydrogen, hydroxy, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C8)-hydroxyalkyl, hydroxycarbonyl-(C1-C8)-alkylene, (C1-C8)-alkoxy, (C1-C8)-alkoxy-(C1-C8)-alkylene, (C1-C8)-alkoxyalkyloxy, (C1-C8)-haloalkoxy, (C3-C10)-cycloalkyl, (C3-C10)-halocycloalkyl, aryl, heteroaryl, (C3-C10)-cycloalkyl-(C1-C8)-alkylene, heterocyclyl, (C2-C8)-alkenyl, (C2-C8)-alkenyloxy, (C2-C8)-alkynyl, (C2-C8)-alkynyloxy, amino, bis[(C1-C8)-alkyl]amino, aryl-(C1-C8)-alkylene, heteroaryl-(C1-C8)-alkylene, heterocyclyl-(C1-C8)-alkylene, (C1-C8)-cyanoalkyl, C(O)R12, C(O)OR12, C(O)NR10R11, SO2R13, R12O(O)C—(C1-C8)-alkylene, arylcarbonyl-(C1-C8)-alkylene, (C1-C8)-alkylcarbonyl-(C1-C8)-alkylene, heteroarylcarbonyl-(C1-C8)-alkylene, heterocyclylcarbonyl-(C1-C8)-alkylene, (C1-C7)-alkylcarbonyloxy-(C1-C8)-alkylene,
• R2 and R9 independently of one another represent hydrogen, hydroxy, halogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C10)-cycloalkyl, aryl, heteroaryl, heterocyclyl, aryl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, 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, arylcarbonyloxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkyl, (C3-C8)-cycloalkylcarbonyloxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkoxy-(C1-C8)-alkyl, C(O)R12, C(O)OR12, C(O)NR10R11, OR12, SR13, SOR13, SO2R13, NR10R11, R10R11N—(C1-C8)-alkyl, cyano-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, hydroxycarbonyl, aminocarbonyl, aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, (C3-C8)-cycloalkylaminocarbonyl-(C1-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, cyano, hydroxy-(C1-C8)-alkyl, or
• R1 and R2 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 optionally has further substitution, or
• R2 and R9 together with the carbon atoms to which they are each 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 optionally has further substitution,
• 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, (C1-C8)-alkoxy-(C1-C8)-alkylcarbonyloxy, aryl-(C1-C8)-alkylcarbonyloxy, heteroarylcarbonyloxy, (C3-C10)-cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (C1-C8)-haloalkylcarbonyloxy, (C2-C8)-alkenylcarbonyloxy, OC(O)OR2, OC(O)SR13, OC(S)OR, OC(S)SR13, OSO2R13, OSO2OR2, OCHO,
• R4 and R7 independently of one another represent hydrogen, hydrothio, hydroxy, halogen, (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, (C3-C10)-halocycloalkyl, (C4-C10)-cycloalkenyl, (C4-C10)-halocycloalkenyl, aryl-(C2-C8)-alkenyl, heteroaryl-(C2-C8)-alkenyl, heterocyclyl-(C2-C8)-alkenyl, aryl-(C2-C8)-alkynyl, heteroaryl-(C2-C8)-alkynyl, heterocyclyl-(C2-C8)-alkynyl, (C3-C10)-cycloalkyl-(C2-C8)-alkynyl, 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, arylcarbonyloxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkyl, (C3-C8)-cycloalkylcarbonyloxy-(C1-C8)-alkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, aryl-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkoxy-(C1-C8)-alkyl, CHO, C(O)R12, C(O)OR12, C(O)NR10R11, OR12, SR13, SOR13, S2R13, NR10R11, R10R11N—(C1-C8)-alkyl, cyano-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, hydroxycarbonyl, (C1-C8)-haloalkoxy-(C1-C8)-alkylthio, (C1-C8)-alkylthio-(C1-C8)-alkylene, (C1-C8)-haloalkylthio-(C1-C8)-alkylthio, (C1-C8)-alkylthio-(C1-C8)-alkylthio, aminocarbonyl, aminocarbonyl-(C1-C8)-alkyl, (C1-C8)-alkylaminocarbonyl-(C1-C8)-alkyl, (C3-C8)-cycloalkylaminocarbonyl-(C1-C8)-alkyl, (C2-C8)-alkenyloxycarbonyl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, cyano, hydroxy-(C1-C8)-alkyl, (C2-C8)-alkenyloxy-(C1-C8)-alkyl, or
• R4 and R7 together with the carbon atom to which they are each 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 optionally has further substitution, when Q represents Q-3, Q-4, Q-8, Q-9, Q-12 and Q-19,
• R5 represents hydrogen, formyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, hydroxy-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C3-C10)-cycloalkyl, (C3-C10)-halocycloalkyl, aryl, heteroaryl, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, heterocyclyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, 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, heterocyclylcarbonyl-(C1-C8)-alkyl, or
• R4 and R5 together with the nitrogen atom or carbon atom to which they are each 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 optionally has further substitution, when Q represents Q-13, Q-14, Q-15, Q-25 and Q-26,
• R6 represents hydrogen or (C1-C8)-alkyl,
• R8 represents hydrogen, halogen, cyano, nitro, hydrothio, hydroxy, NR10R11, OR, SR13, SOR13, SO2R13, thiocyanato, isothiocyanato, formyl, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C10)-haloalkyl, (C2-C8)-haloalkenyl, (C2-C8)-haloalkynyl, (C3-C8)-cycloalkyl, (C3-C10)-halocycloalkyl, (C4-C10)-cycloalkenyl, (C4-C10)-halocycloalkenyl, pentafluorothio, (C1-C8)-alkoxy-(C1-C8)-haloalkyl, (C1-C8)-haloalkoxy-(C1-C8)-haloalkyl, (C1-C8)-haloalkoxy-(C1-C8)-alkyl, aryl, aryl-(C1-C8)-alkyl, heteroaryl, heteroaryl-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C4-C10)-cycloalkenyl-(C1-C8)-alkyl, heterocyclyl, heterocyclyl-(C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkylthio-(C1-C8)-alkyl, (C1-C8)-haloalkylthio-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyl-(C1-C8)-alkyl, C(O)OR12, C(O)NR10R11, C(O)R12, —C═NOR12, —C═NOH, R10R11N—(C1-C8)-alkyl, R12O(O)C—(C1-C8)-alkyl, hydroxycarbonyl, hydroxycarbonyl-(C1-C8)-alkyl, aryl-(C1-C8)-alkynyl, heteroaryl-(C1-C8)-alkynyl, heterocyclyl-(C1-C8)-alkynyl, tris[(C1-C8)-alkyl]silyl-(C2-C8)-alkynyl, bis[(C1-C8)-alkyl](aryl)silyl-(C2-C8)-alkynyl, bisaryl[(C1-C8)-alkyl]silyl-(C2-C8)-alkynyl, (C3-C8)-cycloalkyl-(C2-C8)-alkynyl, aryl-(C2-C8)-alkenyl, heteroaryl-(C2-C8)-alkenyl, heterocyclyl-(C2-C8)-alkenyl, (C3-C8)-cycloalkyl-(C2-C8)-alkenyl, (C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkylaminosulfonylamino, (C3-C8)-cycloalkylaminosulfonylamino, diazo, aryldiazo, tris[(C1-C8)-alkyl]silyl, bis[(C1-C8)-alkyl](aryl)silyl, bisaryl[(C1-C8)-alkyl]silyl,
• R10 and R11 are the same 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, (C3-C10)-halocycloalkyl, (C4-C10)-cycloalkenyl, (C4-C10)-halocycloalkenyl, (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, COR12, SO2R13, (C1-C8)-alkyl-HNO2S—, (C3-C10)-cycloalkyl-HNO2S—, 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, heterocyclyl-(C1-C8)-alkyl,
• R12 represents (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C1-C8)-cyanoalkyl, (C1-C1)-haloalkyl, (C2-C8)-haloalkenyl, (C2-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, (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, 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, (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-C10)-cycloalkyl-(C1-C8)-alkyl, (C4-C10)-cycloalkenyl-(C1-C8)-alkyl, NR10R11,
• R14 and R15 independently of one another represent hydrogen, (C1-C8)-alkyl, halogen, or
• R9 and R15 together with the carbon atoms to which they are each 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 optionally has further substitution,
• and
• W represents oxygen.