2-Amino-4-bicyclylamino-6H-1,3,5-triazines, processes for their preparation and their use as herbicides and plant growth regulators

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

• in which
• R1 and R2 are each independently of one another hydrogen, a group of the formula NR′R″, where R′ and R″ are each independently of one another H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl or (C5-C6)cycloalkenyl, or an acyclic hydrocarbon radical or hydrocarbonoxy radical having in each case 1 to 10 carbon atoms or a heterocyclyl radical, heterocyclyloxy radical, heterocyclylthio radical or heterocyclylamino radical having in each case 3 to 9 ring atoms and 1 to 3 hetero ring atoms from the group consisting of N, O and S, where each of the six last-mentioned radicals is unsubstituted or substituted, or an acyl radical of an organic acid having 1 to 20 carbon atoms, or
• R1 and R2 together with the nitrogen atom of the group NR1R2 are a saturated or unsaturated, nonaromatic heterocyclic radical having 3 to 9 ring atoms and 1 to 4 hetero ring atoms, where the further hetero ring atoms optionally present in addition to the nitrogen atom are selected from the group consisting of N, O and S and the radical is unsubstituted or substituted,
• where each of the carbon-containing radicals R1 and R2 including substituents has 1 to 20 carbon atoms,
• R3 is hydrogen, amino, (C1-C4)alkylamino, di(C1-C4)alkylamino, (C1-C6)alkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, phenyl or heterocyclyl,
• where each of the 10 last-mentioned radicals independently of the others is unsubstituted or substituted and the radical in question including substituents has 1 to 12 carbon atoms, or an acyl radical of the formula -B*-A*, where
• A* is hydrogen or an acyclic or cyclic hydrocarbon radical having 1 to 10 carbon atoms which is unsubstituted or substituted, and
• B* is a divalent group of the formula —CO—, —CO—O—, —CO—NR′—, —S(O)p—or —S(O)p—O—, where p=0, 1 or 2 and R′ is hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, benzyl, cycloalkyl having 3 to 6 carbon atoms or alkanoyl having 1 to 6 carbon atoms,
• where -B*-A* including substituents has 1 to 12 carbon atoms,
• R4 is a radical of the formula -Z1-R6, where Z1 and R6 are as defined below,
• R5 are each independently of one another halogen, cyano, isocyanato, nitro, a radical of the formula -Z2-R7, where Z2 and R7 are as defined below, or
• two adjacent radicals R5 together are a fused-on cycle having 4 to 6 ring atoms which is carbocyclic or contains 1 to 3 hetero ring atoms from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl and oxo,
• R6, R7, R8, R9 are each independently of one another hydrogen, except that R7 is not hydrogen if Z2 is a direct bond, or an acyclic hydrocarbon radical having 1 to 20 carbon atoms or a cyclic hydrocarbon radical or a heterocyclic radical, where each of the three last-mentioned radicals is unsubstituted or substituted,
• or R8 and R9 together with the carbon atom of a group CR8R9 (for Y1 Y2) or two radicals R8 or R9 from two groups Y1 and/or Y2 together with the attached atoms of the groups Y1 and/or Y2 are in each case a carbocyclic radical having 3 to 8 carbon atoms or a heterocyclic radical, where each of the two last-mentioned radicals is unsubstituted or substituted,
• X1, X2, X3, X4 are each independently of one another a carbon atom which is substituted by a hydrogen atom or one of the substituents R5 defined above, or a nitrogen atom, or two adjacent symbols X1, X2, X3 and X4 are in each case together a divalent group of the formula —O—, —S—, —NH— or —NR—, where R is as defined for R3, provided the groups X1, X2, X3, X4 together with the attached C2 unit of the fused-on ring form a carbocyclic or heterocyclic aromatic five- or six-membered ring,
• (Y1)m are m divalent groups Y1, where each group Y1 independently of the other radicals Y1 is a group of the formula —O—, —CO—, —C(═NR*)—, —S(O)q—, —NR*— or —N(O)—, where q=0, 1 or 2 and R* is as defined for R3, or a group of the formula CR8R9, where R8 and R9 are as defined above, and
• Y2 is a group as defined for Y1 or a direct bond,
• where two adjacent groups of the symbol pairs Y1 and Y1 or of the symbol pairs Y1 and Y2 are groups with no heteroatoms having the same meaning, and where the groups (Y1)m and Y2 together with the attached C2 unit of the aromatic ring and the carbon atom attached to R4 form a fused-on carbocyclic or heterocyclic nonaromatic four- to eight-membered ring,
• Z1 and the groups Z2 are each independently of one another a direct bond or a divalent group of the formula —O—, —S(O)p—, —S(O)p—O—, —O—S(O)p—, —CO—, —O—CO—, —CO—O—, —NR′—, —O—NR′—, —NR′—O—, —NR′—CO—, —CO—NR′—, where p=0, 1 or 2 and R′ is hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, benzyl, (C3-C6)cycloalkyl or alkanoyl having 1 to 6 carbon atoms,
• m is 0, 1, 2, 3 or 4 and
• n is 0, 1, 2, 3 or 4.