Synthesis and Antifungal Activity of O, O-Dialkyl O-Aryl Phosphorothioates and Related Compounds:Studies on Organophosphorus Fungicides (Part 2)

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概要

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• In order to examine the structural requirement for the antifungal activity against Rhizoctonia solani a number of O, O-dialkyl O-aryl phosphorothioates and related compounds were prepared and their ED50 values based on the molar concentration for a 50% reduction of the myceiial growth of the fungi were determined by using the agar dilution method. It was found that the methoxyphosphinothioyl moiety and the substituents at 2-, 4-, and 6-positions on benzene ring in the phosphorothioates were essential for enhancing the antifungal activity. In a series of O, O-dimethyl O-(4-substituted-2, 6-dichlorophenyl) phosphorothioates the change in the activity was paraborically related to the variation in both the length and the hydrophobicity of substituents by means of the multiple regression analysis using physicochemical substituent parameters. Moreover, the degree of the activity for a series of O-alkyl O-methyl O-(2, 4, 6-trichlorophenyl) phosphorothioates decreased with an increase of the hydrophobicity of the alkyl group. These results were quite different from those seen in this type of organophosphorus insecticides whose activity is greatly influenced by the electronic factor of benzene ring substituents. On the basis of both the efficacy of antifungal activity and the ease of preparing in a high yield, O, O-dimethyl O-(2, 6-dichloro-4-methylphenyl) phosphorothioate (tolclofos-methyl) was best selected as a practical fungicide for controlling soil borne diseases caused by R. solani.

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