| abstract |
FIELD: organic chemistry, fungicides. SUBSTANCE: invention relates to novel halogen-substituted benzimidazoles of the formula (I) where R 1 , R 2 , R 3 , R 4 means hydrogen, halogen atom, alkoxy-group with 1-4 carbon atoms, group of the formula Z-R 5 where R 5 means unsubstituted phenyl, pyridinyl that can be substituted with trifluoromethyl- group and Z means oxygen, sulfur atom; R 2 and R 3 in common mean unsubstituted or substituted alkylene chain with 3 or 4 links where two (nonadjacent) carbon atoms can be replaced for oxygen atom; A means the group of the formula -SO 2 -R 6 or where Y means oxygen or sulfur atom and R 6 , R 7 , R 8 mean independently each of other alkyl with 1-4 carbon atoms, alkoxy-group with 1-4 carbon atoms, alkenyl with 1-4 carbon atoms, dialkylamino-group, phenyl that can be substituted with nitro-group, methyl, trifluoromethyl-group; 1-pyrrolidinyl, 1- piperidinyl; or thienyl, pyrazolyl, isoxazolyl being each of these residues can be substituted with chlorine atom, amino- group, methyl, methoxy-group, trifluoromethyl-group, methoxycarbonyl; X means halogen atom, and their acid- additive salts also. New compounds exhibit fungicide activity and therefore they are an active substance of fungicide agent as an additional object of invention. Invention relates to also novel intermediate compounds of formulas (IIa) and (IVa) used for synthesis of compounds of the formula (I) where R 9 , R 10 , R 11 , R 12 mean independently each of other hydrogen atom, haloidalkylthio-group or R 10 , R 11 in common with carbon atoms with which they are bound form 5- or 6- membered heterocyclic ring with one or two (nonadjacent) oxygen atoms monosubstituted with halogen atom; X means halogen atom; R 13 and R 14 mean hydrogen atom, haloid- -alkylthio-group. EFFECT: new compounds indicated above, valuable fungicide properties. 7 cl, 3 tbl, 42 ex |