Herbicidal azines

An azine compound of formula (I)

• wherein
• A is a 6-membered heteroaryl having 1 to 3 nitrogen atoms,
• which is substituted by one to four substituents RA, selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, OH, C1-C6-alkoxy, C1-C6-alkylthio, (C1-C6-alkyl)sulfinyl, (C1-C6-alkyl)sulfonyl, amino, (C1-C6-alkyl)amino, di(C1-C6-alkyl)amino, (C1-C6-alkyl) ¬carbonyl, (C1-C6-alkoxy)carbonyl;
• R1 is selected from the group consisting of H, OH, S(O)2NH2, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C1-C6-alkoxy, (C1-C6-alkoxy)-C1-C6-alkyl, (C1-C6-alkyl)-carbonyl, (C1-C6-alkoxy) carbonyl, (C1-C6-alkyl)sulfonyl, (C1-C6-alkylamino)carbonyl, di(C1-C6-alkyl)aminocarbonyl, (C1-C6-alkylamino)sulfonyl, di(C1-C6-alkyl)aminosulfonyl and (C1-C6-alkoxy) sulfonyl, where the aliphatic and cycloaliphatic parts of the 14 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenyl-C1-C6-alkyl, phenylsulfonyl, phenylaminosulfonyl, phenylcarbonyl and phenoxycarbonyl,
• wherein phenyl in the last 6 mentioned radicals are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• R2 is H, halogen, OH, CN, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, (C1-C6-alkoxy)-C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkoxy or (C3-C6-cycloalkyl)-C1-C4-alkoxy, where the aliphatic and cycloaliphatic parts of the 9 aforementioned radicals are unsubstituted, partly or completely halogenated,
• phenyl, phenyl-C1-C6-alkyl,
• wherein phenyl in the last 2 mentioned radicals are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy,
• R3 is selected from the group consisting of H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• R4 is selected from the group consisting of H, halogen, CN, C1-C6-alkyl, C2-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C3-C6-cycloalkenyl and C1-C6-alkoxy-C1-C6-alkyl, where the aliphatic and cycloaliphatic parts of the 7 aforementioned radicals are unsubstituted, partly or completely halogenated;
• or
• R3 and R4 together with the carbon atom to which they are attached form a moiety selected from the group consisting of carbonyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl and three- to six-membered heterocyclyl,
• wherein the C3-C6-cycloalkyl, C3-C6-cycloalkenyl, or three- to six-membered heterocyclyl is unsubstituted or substituted by one to six substituents selected from halogen, CN, C1-C6-alkyl and C1-C6-alkoxy, and wherein the heterocyclyl is a monocyclic saturated or partially unsaturated hydrocarbon having three to six ring members, which contains in addition to the carbon atoms one or two heteroatoms selected from O, S and N;
• and
• R5 is selected from the group consisting of H, OH, S(O)2NH2, CN, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, (C3-C6-cycloalkyl)-C1-C4-alkyl, C1-C6-alkoxy, (C1-C6-alkoxy)-C1-C6-alkyl, (C1-C6-alkyl)-carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)sulfonyl, (C1-C6-alkylamino)carbonyl, di(C1-C6-alkyl)aminocarbonyl, (C1-C6-alkylamino)sulfonyl, di(C1-C6-alkyl)aminosulfonyl and (C1-C6-alkoxy)sulfonyl, where the aliphatic and cycloaliphatic parts of the 14 aforementioned radicals are unsubstituted, partly or completely halogenated, phenyl, phenyl-C1-C6-alkyl, phenyl sulfonyl, phenylaminosulfonyl, phenylcarbonyl and phenoxycarbonyl,
• wherein phenyl in the last 6 mentioned radicals are unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO2, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• including their agriculturally acceptable salts or N-oxides,
• with the proviso that the following compounds are excluded:
• 4-amino-6-[(2-methyl-1H-benzimidazol-5-yl)amino]-1,3,5-triazine-2-carboxylic acid,
• Methyl-4-amino-6-[(2-methyl-1H-benzimidazol-5-yl)amino]-1,3,5-triazine-2-carboxylate,
• Ethyl-4-amino-6-[(2-methyl-1H-benzimidazol-5-yl)amino]-1,3,5-triazine-2-carboxylate,
• N2-(4-methylthiazol-2-yl)-6-pentyl-1,3,5-triazine-2,4-diamine,
• N2-[(5-ethylthio)-1,3,4-thiadiazol-2-yl)]-6-methyl-N4-(2,4,6-trimethylphenyl)-1,3,5-triazine-2,4-diamine,
• 6-methyl-N2-(4-methyl-1,3-benzothiazol-2-yl)-N4-(2,4,6-trimethylphenyl)-1,3,5-triazine-2,4-diamine,
• 2-amino-4-(5-chloro-8-isoquinolylamino)-6-(p-isobutylbenzyl)1,3,5-triazine.