Ihara Chemical Industry Co., Ltd.

Ihara Chemical Kogyo Kabushiki Kaisha

Keiichiro Takagi

Zenichi Sato

Yoji Imamiya

Masamichi Shimizu

Fumiya Tabuchi

Fumio Shimizu

Shoji Kusano

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

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

Thiolcarbamates are prepared by reacting a secondary amine having the formula ##EQU1## wherein R.sub.1 and R.sub.2 are the same or different and each represent hydrogen, lower alkyl, alkoxy, alkenyl, alkoxyalkyl, cycloalkyl, hydroxyalkyl, benzyl or phenyl or R.sub.1 and R.sub.2 combined is a nitrogen containing heterocyclic ring with carbonylsulfide to form an intermediate of an amine salt of a thiolcarbamic acid having the formula ##EQU2## wherein R.sub.1 and R.sub.2 are defined as above, in an organic solvent having the formula ##SPC1## Wherein n is 0, 1 or 2 and R' is hydrogen, halogen or a lower alkyl group which solvent is sparingly soluble or insoluble in water and which dissolves the amine salt of the thiolcarbonic acid, and then reacting the intermediate with an alkyl halide having the formula

Process for preparing a thiolcarbamate

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Keiichiro Takagi