Sumitomo Chemical Company, Limited

Katsutoshi Tanaka

Kunio Mukai

Mitsuru Sasaki

Tadashi Ooishi

Tamon Uematsu

Akira Fujinami

Nobuyuki Kameda

Toshiaki Ozaki

Sigeo Yamamoto

Katsuji Nodera

Shigehiro Ooba

Keiichiro Akiba

Yuzuru Sanemitsu

Novel N-(3,5-dihalophenyl)imide compounds, which exhibit a strong antimicrobial activity against microorganisms including phytopathogenic fungi, parasites of industrial products and pathogenic microorganisms, represented by the formula, ##STR1## wherein X and X' each represent halogens and A represents a substituted ethylene such as chloroethylene, C.sub.1 - C.sub.4 alkylthioethylene, C.sub.1 - C.sub.2 alkyl-ethylene or 1,2-di-C.sub.1 - C.sub.2 -alkyl-ethylene, a cyclopropylene such as 1,3-dimethylcyclopropylene, trimethylene, a cyclohexylene-1,2-, cyclohexenylene-1,2-, cyclohexadienylene-1,2- or o-phenylene. The N-(3,5-dihalophenyl)imide compounds can be obtained by any of methods which produce imide compounds or reaction of an N-(3,5-dihalophenyl)maleimide compound with a mercaptan, a hydrogen halide, phosphorus chloride or thionylchloride.

Antimicrobial composition and method containing

The present invention relates to novel .alpha.-benzylidene-.gamma.-butyrolactone derivatives and processes for the manufacture of them. Further, the present invention pertains to the fungicidal composition containing the same and use thereof.

.alpha.-Benzylidene lactone derivatives

A phenylenediamine compound of the formula: ##SPC1## Wherein R.sub.1 is a lower alkyl group or a phenyl group which may bear one to five substituents, R.sub.2 is a lower alkyl group, A is an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a phenyl group, a cyanoalkyl group, a lower alkylthioalkyl group, a haloalkenyl group, a lower alkoxyalkyl group, a lower alkoxycarbonylalkyl group, a lower alkylcarbamoylalkyl group or a phenylalkyl group which may bear one to five substituents on the benzene ring and X is an oxygen atom or a sulfur atom, which is useful as a pesticide effective in preventing and controlling simultaneously two or more kinds of plant diseases and can be produced by reacting an amidophosphoric ester of the formula: ##SPC2## Wherein R.sub.1, A and X are each as defined above with an alkoxycarbonyl isothiocyanate of the formula: ##EQU1## wherein R.sub.2 is as defined above.

Phosphoryl phenylenediamines

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Takarazuka, Japan

Katsutoshi Tanaka