Ciba-geigy Corporation

Paul Radimerski

Pierre Martin

Peter Baumeister

Milos Rusek

Hansjurg Wetter

Rolf Bader

Peter Flatt

A process for the preparation of 2-alkyl-6-methyl-N(1'-methoxy-2'-propyl)-aniline by catalytic reductive alkylation wherein at least one mole equivalent of methoxyacetone is reacted with one mole equivalent of 2-alkyl-6-methyl-aniline in a liquid medium without an additional solvent, in the presence of a platinized carbon catalyst and hydrogen and in the presence of an acid cocatalyst under a hydrogen pressure of between 2.times.10.sup.5 and 1.times.10.sup.6 Pa at a temperature between 20.degree. and 80.degree. C., characterized in that the reaction mixture contains water from the beginning of the reaction and after the hydrogenation, base is added, the reaction mixture is filtered to separate the catalyst and the title compound recovered from the filtrate. The process is particularly useful for the preparation of N-substituted chloracetanilide herbicides.

Process for the preparation of

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 H.sub.2 N--NH--R to a compound of the formula ##STR1## hydrogenating the compound (III) catalytically to a compound ##STR2## 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 NH.sub.3, to 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole. R in the formulae is hydrogen, --CHO, --COR', --COOR' or --CONH.sub.2, and R' is C.sub.1 -C.sub.4 -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.

Process for producing 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole

A process for the preparation of 2,6-dialkyl-N-alkylanilines is disclosed, which process comprises the reaction of a 2,6-dialkylaniline with an alkanol at 200.degree. to 350.degree. C. in the presence of a copper-containing catalyst which contains 0.05 to 10% by weight of palladium or platinum.

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Therwil, Switzerland

Paul Radimerski