Substituted 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, salts thereof and their use as herbicidally active substances

A substituted 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine compound of formula (I) or a salt thereof

• in which
• R1 represents (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, (C3-C8)-cycloalkoxy, aryl, heteroaryl, heterocyclyl, a bicyclic or a heterobicyclic residue, wherein each of the previously mentioned eight residues is unsubstituted or is independently substituted by one or more residues selected from the group R7,
• R2 represents hydrogen, halogen, formyl, hydroxy, hydrothio, hydroxycarbonyl, aminocarbonyl, aminothiocarbonyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (C1-C8)-alkoxy, (C1-C8) haloalkoxy, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C1-C8)-alkylcarbonyl, (C2-C8)-alkenylcarbonyl, (C2-C8)-alkynylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C2-C8)-haloalkenylcarbonyl, (C2-C8)-haloalkynylcarbonyl, (C1-C8)-alkoxycarbonyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkylthio, (C3-C8)-cycloalkylsulfinyl, (C3-C8)-cycloalkylsulfonyl, (C3-C8)-halocycloalkyl, (C3-C8)-halocycloalkoxy, (C3-C8)-halocycloalkylthio, (C3-C8)-halocycloalkylsulfinyl, (C3-C8)-halocycloalkylsulfonyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C1-C8)-alkyl-(C3-C8)-cycloalkyl, (C3-C8)-cycloalkylcarbonyl, (C3-C8)-cycloalkyl-(C1-C8)-alkylcarbonyl, (C1-C8)-alkylaminocarbonyl, (C2-C12)-dialkylaminocarbonyl, (C1-C8)-alkylaminosulfonyl, (C2-C12)-dialkylaminosulfonyl, tris[(C1-C8)alkyl]silyl, or aryl,
• R3 represents hydrogen, halogen, cyano, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C1-C8)-alkoxy, (C1-C8) haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C3-C8)-cycloalkyl, (C3-C8)-halocycloalkyl, (C3-C8)-cycloalkoxy or (C3-C8)-halocycloalkoxy,
• R4 and R5 independently of one another represent hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C8)-cycloalkyl, (C3-C8)-halocycloalkyl, or R10O—(C1-C8)-alkyl, or
• R4 and R5 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,
• R6 represents hydrogen, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, cyano-(C1-C8)-alkyl, R10O—(C1-C8)-alkyl, R8R9N—(C1-C8)-alkyl, NR8R9, (C3-C10)-cycloalkyl-(C1-C8)-alkyl, C(═O)R10, C(═O)OR10, C(═O)NR8R9, R10O(O)C—(C1-C8)-alkyl, R10(O═)C—(C1-C8)-Alkyl, R8R9N(O)C—(C1-C8)-alkyl, SO2R11, R11S(O)m—(C1-C8)-alkyl, BR12R13, heterocyclyl, heteroaryl, aryl-(C1-C8)-alkyl, heteroaryl-(C1-C8)-alkyl, heterocyclyl-(C1-C8)-alkyl, tris[(C1-C8)alkyl]silyl, bis-[(C1-C8)-alkyl](aryl)silyl, (C1-C8)-alkyl-[bis-(aryl)]silyl, tris-[(C1-C8)-alkyl]silyl-(C1-C8)-alkyl, bis-[(C1-C8)-alkyl](aryl)silyl(C1-C8)-alkyl, or (C1-C8)-alkyl-[bis-(aryl)]silyl-(C1-C8)-alkyl,
• m is 0, 1, 2,
• n is 0, 1, 2,
• R7 represents hydrogen, halogen, formyl, hydroxy, hydroxycarbonyl, nitro, cyano, amino, aminocarbonyl, aminothiocarbonyl, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (C1-C8)-alkoxy, (C1-C8)-haloalkoxy, (C1-C8)-alkylthio, (C1-C8)-haloalkylthio, (C1-C8)-alkylsulfinyl, (C1-C8)-haloalkylsulfinyl, (C1-C8)-alkylsulfonyl, (C1-C8)-haloalkylsulfonyl, (C1-C8)-alkylcarbonyl, (C1-C8)-haloalkylcarbonyl, (C2-C8)-alkenylcarbonyl, (C2-C8)-haloalkenylcarbonyl, (C2-C8)-alkynylcarbonyl, (C2-C8)-haloalkynylcarbonyl, (C1-C8)-alkoxycarbonyl, (C1-C8)-haloalkoxycarbonyl, (C3-C8)-cycloalkyl, (C3-C8)-halocycloalkyl, (C3-C8)-cycloalkoxy, (C3-C8)-halocycloalkoxy, (C3-C8)-cycloalkylthio, (C3-C8)-halocycloalkylthio, (C3-C8)-cycloalkylsulfinyl, (C3-C8)-halocycloalkylsulfinyl, (C3-C8)-cycloalkylsulfonyl, (C3-C8)-halocycloalkylsulfonyl, (C3-C8)-cycloalkyl-(C1-C8)-alkyl, (C1-C8)-alkyl-(C3-C8)-cycloalkyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkyl, (C3-C8)-cycloalkylcarbonyl, (C3-C8)-cycloalkyl-(C1-C8)-alkylcarbonyl, (C1-C8)-alkylamino, (C2-C12)-dialkylamino, (C1-C8)-alkylaminocarbonyl, (C2-C12)-dialkylaminocarbonyl, (C1-C8)-alkylaminosulfonyl, (C2-C12)-dialkylaminosulfonyl or tris[(C1-C8)alkyl]silyl.
• R8 and R9 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, COR10, SO2R11, 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
• R8 and R9 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,
• R10 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, R11(O)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, hydroxy-(C1-C8)-alkyl, hydroxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, hydroxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, hydroxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C1-C8)-alkoxycarbonyl-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroarylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, heterocyclylcarbonyloxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkoxy-(C1-C8)-alkyl, hydroxycarbonyl-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, or hydroxycarbonyl-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl,
• R11 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, or N-azetidinyl, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, and
• R12 and R13 independently of one another represent hydrogen, NR8R9, OR10, or
• R12 and R13 together with the boron 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.