Ihara Chemical Industry Co., Ltd.

Ihara Chemical Kogyo Kabushiki Kaisha

Yoji Imamiya

Zenichi Sato

Keiichiro Takagi

Fumiya Tabuchi

Nobuo Takahashi

Fumio Shimizu

Masanobu Uchiyama

Shoji Kusano

Takaaki Futami

A thiolcarbamate having the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and respectively represent an alkyl, alkoxy, alkenyl, cycloalkyl, hydroxyalkyl, phenyl or benzyl group and R.sub.1 and R.sub.2 can form a ring by binding each other with or without oxygen atom; and R.sub.3 represents a lower alkyl or benzyl group or a substituted benzyl group having one or two substituent of halogen atom, alkyl, alkoxy, alkylthio, nitro, or cyano group, which comprises reacting carbonyl sulfide with a sec-amine having the formula ##STR2## wherein R.sub.1 and R.sub.2 are defined above, in an aqueous medium and then reacting a halogenated hydrocarbon having the formula

Process for producing thiolcarbamates

Carbon monoxide is reacted with sulfur in the vapor phase at 250.degree.-650.degree. C. to prepare carbonyl sulfide, wherein a reactor is used, in which at least the inner surface is made of an alloy consisting essentially of, based on the weight of the alloy, 20-60% of Cr, 40-65% of Ni, 0-10% of Mo, 0-4% of Nb+Ta, and 0-3% of Fe. The reactor not only possesses good corrosion resistance to the gaseous reaction mixture, but also minimizes the reduction in the purity of carbonyl sulfide produced, which reduction occurs with the lapse of operation time.

Process for preparation of carbonyl sulfide

O,O-Dialkyl-S-benzyl thiophosphates are obtained by reacting a diester of phosphorous acid such as dimethyl phosphite or diethyl phosphite, in an organic solvent such as toluene or xylene which is sparingly soluble or insoluble in water, with sulfur and an alkali or alkaline earth metal hydroxide or oxide such as NaOH or Ca(OH).sub.2, extracting the reaction product with water and then reacting the extract with a benzyl halide. In this manner, O,O-dialkyl-S-benzyl thiophosphates useful as agricultural and horticultural bactericidal and insecticidal agents are industrially advantageously obtained in a high purity and in a high yield.

Process for the preparation of O,O-dialkyl-S-benzyl thiophosphates

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Shizuoka, Japan

Yoji Imamiya