Advertisement

Alteration ofO,O-dimethylS-[α-(carboethoxy)benzyl] phosphorodithioate (phenthoate) in citrus, water, and upon exposure to air and sunlight

  • Dennis Y. Takade
  • Myung -Soo Seo
  • T. S. Kao
  • T. R. Fukuto
Article

Abstract

The fate of32P- and14C-labeledO,O-dimethylS-[α-(carboethoxy)benzyl] phosphorodithioate (phenthoate) was determined in citrus, water, and upon exposure to air and sunlight. The products recovered from citrus and glass plates exposed to sunlight were unchanged phenthoate, phenthoate oxon, demethyl phenthoate, mandelic acid,bis- [α-(carboethoxy)benzyl] disulfide,O,O-dimethyl phosphorothioic and phosphorodithioic acid. Similar products generally were found in citrus leaf and fruit extracts. Phenthoate was fairly stable in phosphate buffered water with a half-life of approximately 12 days at pH 8.0. The major hydrolysis products were phenthoate acid, demethyl phenthoate and demethyl phenthoate oxon.

Keywords

Phosphate Hydrolysis Benzyl Glass Plate Hydrolysis Product 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Bender, M. E.: The effect of Malathion on fishes. Ph.D. Dissertation. Dept. of Environ. Sci., Rutgers University, N. J. (1968).Google Scholar
  2. Bonner, W. A.: The preparation, resolution, and absolute configuration ofα-mercaptophenyl acetic acid. J. Org. Chem.33, 1834 (1968).CrossRefGoogle Scholar
  3. Crosby, D. G.: The non-metabolic decomposition of pesticides. Ann. N. Y. Acad. Sci.160, 82 (1969).PubMedGoogle Scholar
  4. Dauterman, W. C., G. B. Viado, J. E. Casida, and R. D. O'Brien: Persistence of dimethoate and metabolites following foliar application to plants. J. Agr. Food Chem.8, 115 (1960).CrossRefGoogle Scholar
  5. Fletcher, J. H., J. C. Hamilton, I. Hechenbleicher, E. I. Hoeberg, B. J. Sertl, and J. T. Cassaday: The synthesis of parathion and closely related compounds. J. Amer. Chem. Soc.72, 2461 (1950).CrossRefGoogle Scholar
  6. Foss, O.: Derivatives of electropositive sulfur. Chem. Abs.41, 1599g (1974).Google Scholar
  7. Hirose, M., I. Miyata, T. Saito, and M. Hayoshi: Residue, degradation and metabolism of14C labeled Elsan® O,O dimethylS-[α-(carboethoxy)benzyl] phosphorodithioate in cabbage,Hime-apples and strawberries. Botyu Kagaku36, 43 (1971).Google Scholar
  8. Holmstead, R. L., T. R. Fukuto, and R. B. March: The metabolism ofO-(4-bromo-2,5-dichlorophenyl)O-methyl phenylphosphonothioate (leptophos) in white mice and cotton plants. Arch. Environ. Contam. Toxicol.1, 133 (1973).CrossRefPubMedGoogle Scholar
  9. Pelegrini, G., and R. Santi: The potentiation of toxicity of organophosphorus compounds containing carboxylic ester functions toward warm-blooded animals by some organo-phosphorus impurities. J. Agr. Food Chem.20, 944 (1972).CrossRefGoogle Scholar
  10. Plapp, F. W., and J. E. Casida: Hydrolysis of the alkyl-phosphate bond in certain dialkyl aryl phosphorothioate insecticides by rats, cockroaches and alkali. J. Econ. Entomol.51, 800 (1958).Google Scholar
  11. Santi, R., M. Rodice, and P. Martinotti: Degradazione, metabolismo e residui di Cidial 32P nelle mele, nelle pere, nelle olive e nell 'olio de oliva.Instituto Ric. Agr. Soc. Montecatini-Edison IX, 87. Contributi 1966–67.Google Scholar

Copyright information

© Springer-Verlag New York Inc. 1976

Authors and Affiliations

  • Dennis Y. Takade
    • 1
  • Myung -Soo Seo
    • 1
  • T. S. Kao
    • 1
  • T. R. Fukuto
    • 1
  1. 1.Department of Entomology, Division of Toxicology and PhysiologyUniversity of CaliforniaRiverside

Personalised recommendations