Abstract
The fields of intermediary metabolism and detoxication mechanisms were largely rewritten after the advent of radiotracer approaches. The same is true for the areas of insecticide metabolism and degradation, and, in small part, also for their mode of action. Radiotracer studies on metabolism and fate of pesticides are no longer just a means of satisfying academic curiosity on compounds which are already in use; on the contrary, they are now generally a necessary and critical step in understanding the persistence and action of a pesticide before it enters actual use. These investigations usually are designed to provide a total accounting, or balance sheet, of the physical and chemical fate of the compound, and frequently they are done under conditions simulating those involved in actual use. Thus, they involve studies on metabolic fate in plants, mammals, and pest species and on photodegradation, in addition to mode of action studies concerning combination or reaction at the site of physiological disruption. Radioanalysis usually can be achieved at nanogram levels of the labeled compound, and the specificity of analysis depends largely on the degree of separation and clean-up before scintillation counting or radioautography. Fortunately, these techniques are, in most instances, adequately developed so that the limiting factor is the experimental design.
Work reported herein was partially supported by AEC Contract AT (11-1)-34, Project Agreement No. 113, and by PHS Grants ES 00049 and GM 12248.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Abdel-Wahab, A. M., and J. E. Casida: Photooxidation of two 4-dimethylaminoaryl methylcarbamate insecticides (Zectran and Matacil) on bean foliage and of alkylaminophenyl methylcarbamates on silica gel chromatoplates. J. Agr. Food Chem. 15, 479 (1967).
R. J. Kuhr, and J. E. Casida: Fate of C 14-carbonyl-labeled aryl methylcarbamate insecticide chemicals in and on bean plants. J. Agr. Food Chem. 14, 290 (1966).
Arthur, B. W., and J. E. Casida: Biological activity and metabolism of Hercules AC-528 components in rats and cockroaches. J. Econ. Entomol. 52, 20 (1959).
Balba, M. H. M., and J. E. Caseda: Synthesis of possible metabolites of methylcarbamate insecticide chemicals. Hydroxy aryl and hydroxyalkylphenyl methylcarbamates. J. Agr. Food Chem. 16, 561 (1968).
Berends, F., C. H. Posxhumus, I. Van Der Sluys, and F. A. Deierkauf: The chemical basis of the “ageing process” of DFP-inhibited pseudocholinesterase. Biochim. Biophys. Acta 34, 567 (1959).
Casida, J. E.: Isomeric substituted-vinyl phosphates as systemic insecticides. Science 122, 597 (1955).
Metabolism of organophosphate insecticides in plants: A review. In: Radioisotopes and radiation in entomology, pp. 49–64. Internat. Atomic Energy Agency, Vienna (1961).
Radiotracer approaches to carbamate insecticide toxicology. In: Radiation and radioisotopes applied to insects of agricultural importance, pp. 223–239. Internat. Atomic Energy Agency, Vienna (1963).
J. L. Engel, E. G. Esaac, F. X. Kamienski, and S. Kuwatsuka: Methylene-C14-dioxyphenyl compounds: Metabolism in relation to their synergistic action. Science 153, 1130 (1966 a).
and Y. Nishizawa: 3′,5′-Diesters of 5-fluoro-2′-deoxyuridine and thymidine: Hydrolysis by esterases in human, mouse, and insect tissue. Biochem. Pharmacol. 15, 627 (1966 b).
L. McBride, and R. P. Niedermeier: Metabolism of 2,2-dichlorovinyl dimethyl phosphate in relation to residues in milk and mammalian tissues. J. Agr. Food Chem. 10, 370 (1962).
and D. M. Sanderson: Toxic hazard from formulating the insecticide dimethoate in methyl ‘cellosolve ’ Nature 189, 507 (1961).
Reaction of certain phosphorothionate insecticides with alcohols and potentiation by breakdown products. J. Agr. Food Chem. 11, 91 (1963).
Cohen, J. A., and R. A. Oosterbaan: The active site of acetylcholinesterase and related esterases and its reactivity towards substrates and inhibitors. In: Cholinesterases and anticholinesterase agents, pp. 299–373. G. B. Koelle, Sub-Ed. Berlin: Springer-Verlag (1963).
Dorough, H. W., and J. E. Casida: Nature of certain carbamate metabolites of the insecticide Sevin. J. Agr. Food Chem. 12, 294 (1964).
N. C. Leeling, and J. E. Casida: Nonhydrolytic pathway in metabolism of N-methylcarbamate insecticides. Science 140, 170 (1963).
Esaac, E. G., and J. E. Casida: Piperonylic acid conjugates with alanine, glutamate, glutamine, glycine, and serine in living house flies. J. Insect Physiol., 14, 913 (1968).
F. X. Kamienski, and J. E. Casida: Unpublished results (1968).
Fukami, J-L, I. Yamamoto, and J. E. Casida: Metabolism of rotenone in vitro by tissue homogenates from mammals and insects. Science 155, 713 (1967).
Hodgson, E., and J. E. Caseda: Mammalian enzymes involved in the degradation of 2,2-dichlorovinyl dimethyl phosphate. J. Agr. Food Chem. 10, 208 (1962).
Horgan, D. J., T. P. Singer, and J. E. Casida: Studies on the respiratory chain-linked reduced nicotinamide adenine dinueleotide dehydrogenase. XIII. Binding sites of rotenone, piericidin A, and amytal in the respiratory chain. J. Biol. Chem. 243, 834 (1968).
Knowles, C. O., and J. E. Casida: Mode of action of organophosphate anthelmintics: Cholinesterase inhibition in Ascaris lumbricoides. J. Agr. Food Chem. 14, 566 (1966).
Krishna, J. G., and J. E. Casida: Fate in rats of the radiocarbon from ten variously labeled methyl- and dimethylcarbamate-C14 insecticide chemicals and their hydrolysis products. J. Agr. Food Chem. 14, 98 (1966).
H. W. Dorough, and J. E. Casida: Synthesis of N-methylcarbamates via methyl isocyanate-C14 and chromatographic purification. J. Agr. Food Chem. 10, 462 (1962).
Kuhr, R. J., and J. E. Casida: Persistent glycosides of metabolites of methylcarbamate insecticide chemicals formed by hydroxylation in bean plants. J. Agr. Food Chem. 15, 814 (1967).
Kuwatsuka, S., and J. E. Casida: Synthesis of methylene-C14-dioxyphenyl compounds: Radioactive safrole, dihydrosafrole, myristicin, piperonyl butoxide, and diastereoisomers of sulfoxide. J. Agr. Food Chem. 13, 528 (1965).
Leeling, N. C., and J. E. Casida: Metabolites of carbaryl (1-naphthyl methylcarbamate) in mammals and enzymatic systems for their formation. J. Agr. Food Chem. 14, 281 (1966).
Menzer, R. E., and J. E. Casida: Nature of toxic metabolites formed in mammals, insects, and plants from 3-(dimethoxyphosphinyloxy)-N,N-dimethyl-cis crotonamide and its N-methyl analog. J. Agr. Food Chem. 13, 102 (1965).
Miskus, R. P., D. P. Blair, and J. E. Casida: Conversion of DDT to DDD by bovine rumen fluid, lake water, and reduced porphyrins. J. Agr. Food Chem. 13, 481 (1965).
Nakatsugawa, T., and P. A. Dahm: Microsomal metabolism of parathion. Biochem. Pharmacol. 16, 25 (1967).
Nishizawa, Y., and J. E. Casida: Synthesis of rotenone-6a-C14 on a semimicro scale. J. Agr. Food Chem. 13, 522 (1965 a).
Synthesis of d-trans-chrysanthemumic acid-C14 and its antipode on a semimicro scale. J. Agr. Food Chem. 13, 525 (1965 b).
S. W. Anderson, and C. Heidelberger: 3′,5′-Diesters of 5-fluoro-2′-deoxyuridine: Synthesis and biological activity. Biochem. Pharmacol. 14, 1605 (1965).
O’Brien, R. D., B. D. Hilton, and L. Gelmour: The reaction of carbamates with Cholinesterase. Mol. Pharmacol. 2, 593 (1966).
Oonnithan, E. S., and J. E. Casida: Metabolites of methyl- and dimethylcarbamate insecticide chemicals as formed by rat liver microsomes. Bull. Environmental Contamination and Toxicol. 1, 59 (1966).
Oxidation of methyl- and dimethylcarbamate insecticide chemicals by microsomal enzymes and anticholinesterase activity of the metabolites. J. Agr. Food Chem. 16, 28 (1968).
Roger, J-C., H. Chambers, and J. E. Casida: Nicotinic acid analogs: Effects on response of chick embryos and hens to organophosphate toxicants. Science 144, 539 (1964).
D. G. Upshall, and J. E. Casida: Unpublished results (1968).
Schmidt, C. H., and P. A. Dahm: The synthesis of C14-labeled piperonyl butoxide and its fate in the Madeira roach. J. Econ. Entomol. 49, 729 (1956).
Shrivastava, S. P., M. Tsukamoto, and J. E. Casida: Unpublished results (1968).
Smith, G. N., B. S. Watson, and F. S. Fischer: Investigations on Dursban insecticide. Uptake and translocation of [36Cl] O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate and [14C] O,O-diethyl O-3,5,6-triehloro-2-pyridyl phosphorothioate by beans and corn. J. Agr. Food Chem. 15, 127 (1967).
Stiasni, M., D. Rehbinder, and W. Deckers: Absorption, distribution, and metabolism of O-(4-bromo-2,5-dichlorophenyl) -O,O-dimethylphosphorothioate in the rat. J. Agr. Food Chem. 15, 474 (1967).
Tsukamoto, M., and J. E. Casida: Albumin enhancement of oxidative metabolism of methylcarbamate insecticide chemicals by the house fly microsome-NADPH2 system. J. Econ. Entomol. 60, 617 (1967 a).
Metabolism of methylcarbamate insecticides by the NADPH2 — requiring enzyme system from house flies. Nature 213, 49 (1967 b).
S. P. Shrivastava, and J. E. Casida: Biochemical genetics of house fly resistance to carbamate insecticide chemicals. J. Econ. Entomol. 61, 50 (1968).
Upshall, D. G., J-C. Roger, and J. E. Casida: Biochemical studies on the teratogenic action of Bidrin and other neuroactive agents in developing hen eggs. Biochem. Pharmacol. 17, 1529 (1968).
Winteringham, F. P. W., and R. W. Disney: A radiometric study of cholinesterase and its inhibition. Biochem. J. 91, 506 (1964).
Yamamoto, I., and J. E. Casida: O-Demethyl Pyrethrin II analogs from oxidation of Pyrethrin I, allethrin, dimethrin and phthalthrin by a house fly enzyme system. J. Econ. Entomol. 59, 1542 (1966).
E. C. Kimmel, J. L. Engel, and J. E. Casida: Unpublished results (1968).
Zubairi, M. Y., and J. E. Casida: Detoxication of dimetilan in cockroaches and houseflies J. Econ. Entomol. 58, 403 (1965).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1969 Springer-Verlag New York Inc.
About this paper
Cite this paper
Casida, J.E. (1969). Radiotracer studies on metabolism, degradation, and mode of action of insecticide chemicals. In: Gunther, F.A. (eds) Residues of Pesticides and Other Foreign Chemicals in Foods and Feeds / Rückstände von Pesticiden und anderen Fremdstoffen in Nahrungs- und Futtermitteln. Residue Reviews / Rückstands-Berichte, vol 25. Springer, New York, NY. https://doi.org/10.1007/978-1-4615-8443-8_13
Download citation
DOI: https://doi.org/10.1007/978-1-4615-8443-8_13
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4615-8445-2
Online ISBN: 978-1-4615-8443-8
eBook Packages: Springer Book Archive