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The Chemistry and Mode of Action of the Insecticide O,O-Diethyl O-p-Methylsulfinylphenyl Phosphorothionate and Its Analogues1

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Abstract:

The insecticide O,O-diethyl O-p-methylsulfinylphenyl phosphorothionate (Bayer 25141) was studied with regard to its chemical instability to heat, hydrolysis, and oxidation and to the effect of the products formed upon insect toxicity. The compound is readily oxidized to the sulfone and upon heating undergoes internal oxidation-reduction to also form the sulfide. Additionally, the compound apparently isomerizes very readily to form the S-ethyl-isomer. The oxidation and isomerization products also form in aqueous systems such as the insect body and as they possess enhanced anticholinesterase activity apparently contribute to the mechanism of toxic action which appears to be that of inhibition of cholinesterase. The bimolecular rate constant for reaction with cholinesterase and the hydroxide-ion catalyzed hydrolysis constant for p-substituted methylthio-, methylsulfinyl-, and methylsulfonylphenyl diethyl phosphates and phosphorothionates can be satisfactorily correlated with the electron-withdrawing capacities of the aryl substituents.

Document Type: Research Article

Publication date: February 1, 1959

More about this publication?
  • Journal of Economic Entomology is published bimonthly in February, April, June, August, October, and December. The journal publishes articles on the economic significance of insects and is divided into the following sections: apiculture & social insects; arthropods in relation to plant disease; forum; insecticide resistance and resistance management; ecotoxicology; biological and microbial control; ecology and behavior; sampling and biostatistics; household and structural insects; medical entomology; molecular entomology; veterinary entomology; forest entomology; horticultural entomology; field and forage crops, and small grains; stored-product; commodity treatment and quarantine entomology; and plant resistance. In addition to research papers, Journal of Economic Entomology publishes Letters to the Editor, interpretive articles in a Forum section, Short Communications, Rapid Communications, and Book Reviews.
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