2,4-diamino-1,3,5-triazines, their preparation and their use as herbicides and plant growth regulators

A compound of the formula (I) or salt thereof

• in which
• R1 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)hydroxyalkyl, (C1-C4)alkoxy-(C1-C4)-alkyl or benzyl,
• R2 and R3 independently of one another are hydrogen , amino , formyl,
• (C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C6)alkenyl, (C2-C6) alkynyl, (C1-C4)alkylamino-(C1-C4)alkyl, di-[(C1-C4)alkyl]-amino-(C1-C4)alky or phenyl, phenyl-(C1-C4)alkyl or phenoxy-carbonyl or one of the three last-mentioned radicals which is substituted up to three times in the phenyl moiety by radicals of the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkoxy-carbonyl, or
• R2 and R3, together with the nitrogen atom of the group NR2R3, are a heterocyclic radical having 3 to 6 ring atoms and 1 to 2 hetero-ring atoms, any further hetero-ring atoms in addition to the nitrogen atom being selected from the group consisting of N and O, and the radical being unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl and oxo,
• R4 is hydrogen, amino, formyl, (C1-C4)alkyl, di-[(C1-C4)alkyl]-amino, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C4)dialkylamino-(C1-C4)alkyl, phenyl, phenoxy-(C1-C4)alkyl, phenyl-(C1-C4)alkyl, phenoxy-carbonyl, phenylamino-carbonyl or one of the five last-mentioned radicals which is mono-to trisubstituted in the phenyl moiety by radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkoxy-carbonyl,
• R5 is ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, and tert-butyl,
• R6 hydrogen, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, di-[(C1-C4)-alkyl]amino-(C1-C4)alkyl, phenyl, phenoxy-(C1-C4)alkyl, phenyl-(C1-C4)alkyl or one of the three last-mentioned radicals which is mono- to trisubstituted in the phenyl moiety by radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkoxy-carbonyl, or
• R5 and R6 together are an alkylene chain having 2 to 4 carbon atoms which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl and oxo,
• (R7)n are n radicals R7 which, in the case of n=2, 3, 4 or 5, are identical or different, R7 in each case being halogen, hydroxyl, amino, nitro, formyl, aminocarbonyl, carboxyl, cyano, thiocyanato, (C1-C6)alkyl, (C1-C4)alkoxy, halo-(C1-C4)alkyl, halo-(C1-C4)alkoxy, hydroxy-(C1-C4)alkyl, hydroxy-(C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)-alkoxy, halo-(C1-C4)alkoxy-(C1-C4)alkyl, halo-(C1-C4)alkoxy-(C1-C4)alkoxy, (C3-C6)cycloalkyl, halo-(C3-C6)cycloalkyl, (C2-C6)alkenyl, halo-(C2-C6)alkenyl, (C2-C6)alkynyl, halo-(C2-C6)alkynyl, (C1-C4)alkylcarbonyl, (C1-C4)haloalkyl-carbonyl, (C3-C6)cycloalkyloxy, halo-(C3-C6)cycloalkyloxy, (C3-C6)cycloalkylcarbonyl, halo-(C3-C6)cycloalkylcarbonyl, (C1-C4)alkoxycarbonyl, halo-(C1-C4)alkoxycarbonyl, (C1-C4)alkylcarbonyloxy, halo-(C1-C4)alkylcarbonyloxy, (C1-C4)alkylcarbonyl-(C1-C4)alkyl, (C1-C4)alkoxycarbonyl-(C1-C4)alkyl, (C1-C4)alkylcarbonyloxy-(C1-C4)alkyl, (C1-C4)alkylthio, halo-(C1-C4)alkylthio, (C1-C4)alkylamino, di-[(C1-C4)alkyl]-amino, (C1-C6)alkanoylamino, N-[(C1-C6)alkanoyl]-N-[(C1-C4)alkyl]-amino, (C1-C6)alkanoylamino-(C1-C4)alkyl, N-[(C1-C6)alkanoyl]-N-[(C1-C4)alkyl]-amino-(C1-C4)alkyl or
• phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenoxy-(C1-C4)alkyl, phenylcarbonyl-(C1-C4)alkyl, phenyl-(C1-C4)alkyl, phenyl-(C2-C6)-alkenyl, phenyl-(C1-C6)alkynyl,
• or one of the 10 last-mentioned radicals which is substituted in the cyclic moiety by one or more radicals from the group consisting of halogen, hydroxyl, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)-haloalkyl and (C1-C4)haloalkoxy, or two adjacent radicals R7 together are a fused-on cycle having 4 to 6 ring atoms which is carbocyclic and which is unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C1-C4)alkyl and oxo,
• X is a group of the formula —O— or —NR*—, R* being hydrogen or methyl, and
• n is 0, 1, 2, 3, 4 or 5;
• or wherein
• a1) R1 is (C1-C4)haloalkyl,
• R2, R3, R4, R6 are each hydrogen,
• R5 is methyl,
• n is the number 3, 4 or 5,
• X is an oxygen atom and
• (R7)n are n radicals R7 which are identical or different,
• R7 in each case being halogen, hydroxyl, amino, nitro, formyl, carboxyl, cyano, (C1-C6)alkyl, (C1-C4)alkoxy, halo-(C1-C4)alkyl, halo-(C1-C4)alkoxy, hydroxy-(C1-C4)alkyl, hydroxy-(C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl, halo-(C1-C4)alkoxy-(C1-C4)alkyl, halo-(C1-C4)alkyloxy-(C1-C4)-alkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C3-C6)cycloalkyl, halo-(C3-C6)cycloalkyl, (C1-C4)alkenyl, halo-(C2-C4)alkenyl, (C2-C4)alkynyl, halo-(C2-C4)alkynyl, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl, (C1-C4)alkylcarbonyloxy, (C1-C4)alkylcarbonyl-(C1-C4)alkyl, (C1-C4)alkylthio, (C1-C4)alkylamino, di-[(C1-C4)-alkyl]-amino or
• phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenoxy-(C1-C4)alkyl, phenylcarbonyl-(C1-C4)alkyl, phenyl-(C1-C4)alkyl or one of the 8 last-mentioned radicals which is substituted in the phenyl moiety by one or more radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl and (C1-C4)haloalkoxy, or two adjacent radicals R7 together are a fused-on cycle having 4 to 6 ring atoms, which is carbocyclic and which is unsubstituted or substituted by one more radicals (C1-C4)alkyl, or
• a2) R1 is (C1-C4)haloalkyl,
• R2, R3, R4, R6 are each hydrogen,
• R5 is methyl,
• n is the number 1 or 2,
• X is an oxygen atom,
• (R7)n are n radicals R7 which, in the case of n=2, are defined the same, R7 in each case being chlorine, bromine, iodine, hydroxyl, amino, nitro, formyl, carboxyl, cyano, (C2-C4)alkoxy, methyl which is substituted by one or more radicals from the group consisting of chlorine, bromine and iodine, (C2-C4)haloalkyl, halo-(C1-C4)alkoxy, hydroxy-(C1-C4)alkyl, hydroxy-(C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl, halo-(C1-C4)alkoxy-(C1-C4)alkyl, halo-(C1-C4)alkyloxy-(C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C3-C6)cycloalkyl, halo-(C3-C6)cycloalkyl, (C2-C4)alkenyl, halo-(C2-C4)alkenyl, (C2-C4)alkynyl, halo-(C2-C4)alkynyl, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl, (C1-C4)alkylcarbonyloxy, (C1-C4)alkylcarbonyl-(C1-C4)alkyl, (C1-C4)alkylthio, (C1-C4)alkylamino, di-[(C1-C4)alkyl]-amino or phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenoxy-(C1-C4)alkyl, phenylcarbonyl-(C1-C4)alkyl, phenyl-(C1-C4)alkyl or one of the 8 last-mentioned radicals which is substituted in the phenyl moiety by one or more radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl and (C1-C4)haloalkoxy, or
• two adjacent radicals R7 together are a fused-on cycle having 4 to 6 ring atoms, which is carbocyclic and which is unsubstituted or substituted by one or more radicals (C1-C4)alkyl, or
• a3) R1 is (C1-C4)haloalkyl,
• R2, R3, R4, R6 are each hydrogen,
• R5 is methyl,
• n is the number 2,
• X is an oxygen atom and
• (R7)n are the two radicals R7, the two radicals R7 being structurally different and otherwise as defined above under al), or else two adjacent radicals R7 together are a fused-on cycle having 4 to 6 ring atoms, which is carbocyclic and which is unsubstituted or substituted by one or more radicals (C1-C4)alkyl, or
• b1) R1 is (C1-C4),alkyl which is unsubstituted or substituted by 1 to 4 substituents from the group consisting of (C1-C4)alkoxy and hydroxyl,
• R2, R3, R4, R6 are each hydrogen,
• R5 is methyl,
• n is the number 1, 2, 3 or 4,
• X is an oxygen atom and
• (R7)n are n radicals R7 which, in the case of n=2, 3 or 4, are identical or different, R7 in each case being hydroxvl, amino, nitro, formyl, carboxyl, cyano, (C1-C4)alkoxy, halo-(C1-C4)alkyl, halo-(C1-C4)alkoxy, hydroxy-(C1-C4)alkyl, hydroxy-(C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl, halo-(C1-C4)alkoxy-(C1-C4)alkyl, halo-(C1-C4)alkyloxy-(C1-C4)-alkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C3-C6)cycloalkyl, halo-(C3-C6)cycloalkyl, (C2-C4)alkenyl, halo-(C2-C4)alkenyl, (C2-C4)alkynyl, halo-(C2-C4)alkynyl, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl, (C1-C4)alkylcarbonyloxy, (C1-C4)alkylcarbonyl-(C1-C4)alkyl, (C1-C4)alkylthio, halo-(C1-C4)alkylthio, (C1-C4)alkylamino, di-(C1-C4)-alkyl]-amino or
• phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenoxy-(C1-C4)alkyl, phenylcarbonyl-(C1-C4)alkyl, phenyl-(C1-C4)alkyl or one of the 8 last-mentioned radicals which is substituted in the phenyl moiety by one or more radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl and (C1-C4)haloalkoxy, or
• two adjacent radicals R7 together are a fused-on cycle having 4 to 6 ring atoms, which is carbocyclic and which is unsubstituted or substituted by one or more radicals (C1-C4)alkyl.