MANUFACTURE OF 1-(2-(2,4-DICHLOROPHENYL)PENTYL)- 1H-1,2,4-TRIAZOLE AND NOVEL HYDRAZONE AND HYDRAZINE DERIVATIVE

摘要

1-[2-(2,4-Dichlorophenyl)-pentyl]-1H-1,2,4-triazole can be produced, in a novel, simple, economical and isomer-free form, by reacting 2-(2,4-dichlorophenyl)-valeronitrile, in the presence of hydrogen, an acid and a hydrogenation catalyst, with a compound H2N-NH-R to a compound of the formula IMAGE (III) hydrogenating the compound (III) catalytically to a compound IMAGE (IV) hydrolysing compounds (IV) wherein R is not hydrogen, and converting the compounds (IV) wherein R=H, or salts thereof, with formamide and/or [3-(dimethylamino)-2-azaprop-2-en-1-ylidene]-dimethylammonium chloride, into 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole, or converting compounds (IV) wherein R=-COR', with aqueous formic acid, into the corresponding N,N'-bisformyl derivatives, and reacting these with formamide, optionally in the presence of NH3, to 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole. R in the formulae is hydrogen, -CHO, -COR', -COOR' or -CONH2, and R' is C1-C4-alkyl, benzyl or phenyl. 1-[2-(2,4-Dichlorophenyl)-pentyl]-1H-1,2,4-triazole exhibits fungicidal activity, and can be used to control phytopathogenic fungi.