Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Studies on Biological Activity of Cyclic Imide Compounds
Part I. Antimicrobial Activity of 3-Phenyloxazolidine-2, 4-diones and Related Compounds
Akira FUJINAMIToshiaki OZAKIShigeo YAMAMOTO
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1971 Volume 35 Issue 11 Pages 1707-1719

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Abstract

The structure-activity relationships of 3-phenyloxazolidine-2, 4-diones, 3-phenyl-4-imino-oxazolidine-2-ones and N-phenylcarbamates were investigated on Sclerotinia sclerotiorum by the agar medium dilution method. In addition, antimicrobial spectra of several compounds against other 15 pathogenic microbes were investigated by the same method. In each series, 3, 5-dihalo-substituents on benzene ring are essential to high antifungal activity against Sclerotinia sclerotiorum and in the case of N-phenylcarbamates, it is necessary that the α-position of alcohol moiety is substituted by such a group as cyano group, ethoxy-carbonyl group or carbamoyl group. α-Cyanoisopropyl N-(3, 5-dichlorophenyl) carbamate, 3-(3', 5'-dichlorophenyl)-5, 5-dimethyl-4-iminooxazolidine-2-one and 3-(3', 5'-dichlorophenyl)-5, 5-dimethyloxazolidine-2, 4-dione were the most effective and completely inhibited the mycelial growth of Sclerotinia sclerotiorum at 3.2 pM (about 1.0ppm). In general, 3-(3', 5'-dichlorophenyl) oxazolidine-2, 4-diones and related compounds are highly active against Sclerotinia sclerotiorum and Botrytis cinerea, and fairly active against Cochliobolus miyabeanus, Pellicularia filamentosa, Pellicularia sasakii and Alternaria kikuchiana.

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