Extramicrosomal Metabolism of Insecticides

  • W. C. Dauterman


This chapter will be restricted to a discussion of the metabolic reactions of insecticides which are not mediated by either the mixed-function oxidases (Chapter 2) or the conjugation enzymes (Chapter 5). Emphasis will be placed on in vitro systems, particularly those in which the enzymes have been purified. The enzymes that catalyze the extramicrosomal metabolism of insecticides may be associated with specific subcellular fractions or may be more broadly distributed among several; in general, their natural biological functions are not well understood.


Juvenile Hormone Organophosphorus Compound Styrene Oxide Organophosphorus Insecticide Juvenile Hormone Analogue 
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  1. Abernathy, C. O., and Casida, J. E., 1973, Pyrethroid insecticides: Esterase cleavage in relation to selective toxicity, Science 179:1235.PubMedGoogle Scholar
  2. Abernathy, C. O., Ueda, K., Engel, J. L., Gaughan, L. C., and Casida, J. E., 1973, Substrate-specificity and toxicological significance of pyrethroid-hydrolyzing esterases of mouse liver microsomes, Pestic. Biochem. Physiol. 3:300.Google Scholar
  3. Ahmed, M. K., Casida, J. E., and Nichols, R. E., 1958, Significance of rumen fluid with particular reference to parathion. J. Agr. Food Chem. 6:740.Google Scholar
  4. Aldridge, W. N., 1953a, Serum esterases. 1. Two types of esterase (A and B) hydrolysing p-nitrophenyl acetate, propionate and butyrate, and a method for their determination, Biochem. J. 53:110.PubMedGoogle Scholar
  5. Aldridge, W. N., 1953, Serum esterases. 2. An enzyme hydrolyzing diethyl p-nitrophenyl phosphate (E600) and its identity with A-esterase of mammalian sera, Biochem. J. 53:117.PubMedGoogle Scholar
  6. Augustinsson, K. B., and Casida, J. E., 1959, Enzymic hydrolysis of N:N-dimethylcarbamoyl fluoride, Biochem. Pharmacol. 3:60.PubMedGoogle Scholar
  7. Augustinsson, K. B., and Heimburger, G., 1954, Enzymatic hydrolysis of oranophosphorus compounds. IV. Specificity Studies, Acta Chem. Scand. 8:1533.Google Scholar
  8. Becker, E. L., and Barbaro, J. F., 1964, The enzymatic hydrolysis of p-nitrophenyl ethyl phosphonates by mammalian plasma, Biochem. Pharmacol. 13:1219.PubMedGoogle Scholar
  9. Behal, F. J., Little, G. H., and Klein, R. A., 1968, Arylamidase of liver, Biochim. Biophys. Acta 178:118.Google Scholar
  10. Bridges, P. M., 1957, Absorption and metabolism of [14C] allethrin by the adult housefly, Musca domestica L., Biochem. J. 66:316.PubMedGoogle Scholar
  11. Brooks, G. T., 1973, Insect epoxide hydrase inhibition by juvenile hormone analogues and metabolic inhibitors, Nature (London) 245:382.Google Scholar
  12. Brooks, G. T., 1974, Inhibitors of cyclodiene epoxide ring hydrating enzymes of the blowfly, Calliphora erythrocephala. Pestic. Sci. 5:177.Google Scholar
  13. Brooks, G. T., and Harrison, A., 1969, Hydration of HEOD (dieldrin) and the heptachlor epoxide by microsomes from liver of pig and rabbits. Bull. Environ. Contam. Toxicol. 4:352.Google Scholar
  14. Brooks, G. T., Lewis, S. E., and Harrison, A., 1968, Selective metabolism of cyclodiene insecticide enantiomers by pig liver microsomal enzymes, Nature 220:1034.PubMedGoogle Scholar
  15. Brooks, G. T., Harrison, A., and Lewis, S. E., 1970, Cyclodiene epoxide ring hydration by microsomes from mammalian liver and houseflies, Biochem. Pharmacol 19:255.PubMedGoogle Scholar
  16. Bull, D. L., and Lindquist, D. A., 1964, Metabolism of 3-hydroxy-N, N-dimethyl crotonamide dimethyl phosphate by cotton plants, insects, and rats, J. Agr. Food Chem. 12:310.Google Scholar
  17. Casida, J. E., and Augustinsson, K. B., 1959, Reaction of plasma albumin with 1-naphthyl N-methylcarbamate (the insecticide sevin) and certain other esters, Biochim. Biophys. Acta 36:411.PubMedGoogle Scholar
  18. Casida, J. E., Augustinsson, K. B., and Jonsson, G., 1960, Stability, toxicity and reaction mechanism with esterases of certain carbamate insecticides, J. Econ. Entomol 53:205.Google Scholar
  19. Casida, J. E., Kimmel, E. C., Elliott, M., and Janes, N. F., 1971, Oxidative metabolism of pyrethrins in mammals, Nature (London) 230:326.Google Scholar
  20. Chamberlain, R. W., 1950, An investigation on the action of piperonyl butoxide with pyrethrum, Am. J. Hyg. 52:153.PubMedGoogle Scholar
  21. Chamberlain, W. F., Gatterdam, P. E., and Hopkins, D. E., 1961, The metabolism of P32-labeled dimethoate in sheep, J. Econ. Entomol. 54:733.Google Scholar
  22. Chen, P. R. S., and Dauterman, W. C., 1971a, Alkylamidase of sheep liver, Biochim. Biophys. Acta 250:216.PubMedGoogle Scholar
  23. Chen, P. R. S., and Dauterman, W. C., 1971, Studies on the toxicity of dimethoate analogs and their hydrolysis by sheep liver amidase, Pestic. Biochem. Physiol. 1:340.Google Scholar
  24. Chen, P. R., Tucker, W. P., and Dauterman, W. C., 1969, The structure of biologically-produced malathion monoacid, J. Agr. Food Chem. 17:86.Google Scholar
  25. Christman, A. A., and Lewis, H. B., 1921, Lipase studies. I. The hydrolysis of the esters of some dicarboxylic acids by the lipase of liver, J. Biol. Chem. 47:495.Google Scholar
  26. Cook, J. W., 1957, In vitro destruction of some organophosphate pesticides by bovine rumen fluid, J. Agr. Food Chem. 5:859.Google Scholar
  27. Cook, J. W., and Yip, G., 1958, Malathionase. II. Identity of a malathion metabolite, J. Assoc. Off. Agr. Chem. 41:407.Google Scholar
  28. Cook, J. W., Blake, J. R., Yip, G., and Williams, M., 1958, Malathionase. I. Activity and inhibition, J. Assoc. Off. Agr. Chem. 41:399.Google Scholar
  29. Dansette, P. M., Yagi, H., Jerina, D. M., Daly, J. W., Levin, W., Lu, A. Y. H., Kuntzman, R., and Conney, A. H., 1974, Assay and partial purification of epoxide hydrase from rat liver microsomes, Arch. Biochem. Biophys. 164:511.PubMedGoogle Scholar
  30. Dauterman, W. C., 1971, Biological and non-biological modifications of organophosphorus compounds, Bull. WHO 44:133.PubMedGoogle Scholar
  31. Dauterman, W. C., and Main, A. R., 1966, The relationship between acute toxicity and in vitro inhibition and hydrolysis of a series of carbalkoxy homologs of malathion, Toxicol. Appl. Pharmacol. 9:409.Google Scholar
  32. Dauterman, W. C., Casida, J. E., Knaak, J. B., and Kowalczyk, T., 1959, Metabolism of organophosphorus insecticides: Metabolism and residues associated with oral administration of dimethoate to rats and three lactating cows, J. Agr. Food Chem. 7:188.Google Scholar
  33. Dicowsky, L., and Morello, A., 1971, Glutathione-dependent degradation of 2,2-dichlorovinyl dimethyl phosphate (DDVP) by the rat, Life Sci. 10:103.Google Scholar
  34. Donninger, C., Nobbs, B. T., and Wilson, K., 1971, An enzyme catalyzing the hydrolysis of phosphoric acid diesters in rat liver. Biochem. J. 122:51p.PubMedGoogle Scholar
  35. Douch, P. G., and Smith, J. N., 1971, Metabolism of m-tert.-butylphenyl, N-methylcarbamate in insects and mice, Biochem. J. 125:385.PubMedGoogle Scholar
  36. Elliott, M., and Casida, J. E., 1972, Optically pure pyrethroids labeled with deuterium and tritium in the methylcyclopentenonyl ring, J. Agr. Food Chem. 20:295.Google Scholar
  37. Elliott, M., Kimmel, E. C., and Casida, J. E., 1969, 3H-Pyrethrin I and-pyrethrin II: Preparation and use in metabolism studies, Pyrethrum Post 10:3.Google Scholar
  38. Elliott, M., Janes, N. F., Kimmel, E. G., and Casida, J. E., 1972, Metabolic fate of pyrethrin I, pyrethrin and allethrin administered orally to rats. J. Agr. Food Chem. 20:300.Google Scholar
  39. Eto, M., 1974, Organophosphorus Pesticides: Organic and Biological Chemistry, CRC press, Cleveland.Google Scholar
  40. Eto, M., Oshima, Y., Kitakata, S., Tanaka, F., and Kojima, K., 1965, Studies on saligenin cyclic phosphorus esters with insecticidal activity. X. Synergism of malathion against susceptible and resistant insects, Botyu-Kagaku 31:33.Google Scholar
  41. Fest, C., and Schmidt, K. J., 1973, The Chemistry of Organophosphorus Pesticides, Springer, New York.Google Scholar
  42. Fukami, J., Shishido, T., Fukuhaga, K., and Casida, J. E., 1969, Oxidative metabolism of rotenone in mammals, fish and insects and its relation to selective toxicity, J. Agr. Food Chem. 17:1217.Google Scholar
  43. Gardocki, J. F., and Hazelton, L. W., 1951, Urinary excretion of the metabolic products of parathion following intraveneous injection, J. Ann. Pharm. Assoc. Sci. Ed. 40:491.Google Scholar
  44. Gillette, J. R., 1971, Reductive enzymes, in: Concepts of Biochemical Pharmacology, Part 2 (B. B. Brodie and J. R. Gillette, ed.), pp. 349–361, Springer, New York.Google Scholar
  45. Hassan, A., and Dauterman, W. C., 1968, Studies on the optically active isomers of O, O-diethyl malathion and O, O-diethyl malaoxon, Biochem. Pharmacol. 17:1431.PubMedGoogle Scholar
  46. Heath, D. F., 1961, Organophosphorus Poisons, Pergamon Press, New York.Google Scholar
  47. Hitchcock, M., and Murphy, S. D., 1967, Enzymatic reduction of O, O-diethyl-(4-nitrophenyl)phosphorothioate, O, O-diethyl O-(4-nitrophenyl)phosphate, and O-ethyl O-(4-nitrophenyl)benzene thiophosphonate by tissues from mammals, birds and fishes, Biochem. Pharmacol. 16:1801.PubMedGoogle Scholar
  48. Hodgson, E., and Casida, J. E., 1962, Mammalian enzymes involved in the degradation of 2,2-dichlorvinyl dimethyl phosphate, J. Agr. Food Chem. 10:208.Google Scholar
  49. Hopkins, T. L., and Robbins, W. E., 1957, The adsorption, metabolism and excretion of 14C-labeled allethrin by houseflies. J. Econ. Entomol. 50:684.Google Scholar
  50. Jao, L. T., and Casida, J. E., 1974, Insect pyrethroid-hydrolyzing esterases, Pest. Biochem. Physiol. 4:465.Google Scholar
  51. Jarczyk, H. J., 1966, The influence of esterases in insects on the degradation of organophosphates of the E.605 series, Pflanzenschutz-Nachr. Bayer 19:1.Google Scholar
  52. Jerina, D. M., and Daly, J. W., 1974, Arene oxides: A new aspect of drug metabolism, Science 185:573.PubMedGoogle Scholar
  53. Jerina, D. M., Daly, J. W., Jefferey, A. M., and Gibson, D. T., 1971, cis-l,2-Dihydroxyl-l,2-dihydro-naphthalene: A bacterial metabolite from naphthalene, Arch. Biochem. Biophys. 142:394.PubMedGoogle Scholar
  54. Johnson, M. K., 1965, The influence of some aliphatic compounds on rat liver glutathione levels, Biochem. Pharmacol. 14:1383.PubMedGoogle Scholar
  55. Kojima, K., 1961, Studies on the Selective Toxicity and Detoxication of Organophosphorus Compounds, special report of the Ton Noyaku Co., Odawara, Japan.Google Scholar
  56. Kojima, K., and O’Brien, R. D., 1968, Paraoxon hydrolyzing enzymes in rat liver, J. Agr. Food Chem. 16:574.Google Scholar
  57. Korte, F., and Arent, H., 1965, Metabolism of insecticides IX (1) isolation and identification of dieldrin metabolites from urine of rabbits after oral administration of dieldrin-14C, Life Sci. 4:2017.PubMedGoogle Scholar
  58. Krueger, H. R., and Casida, J. E., 1961, Hydrolysis of certain organophosphates insecticides by housefly enzymes, J. Econ. Entomol. 54:239.Google Scholar
  59. Leeling, N. C., and Casida, J. E., 1966, Metabolites of carbaryl (1-naphthylmethylcarbamate) in mammals and enzymatic systems for their formation, J. Agr. Food Chem. 14:281.Google Scholar
  60. Lenz, D. E., Deguehery, L. E., and Holton, J. S., 1973, On the nature of the serum enzyme catalyzing paraoxon hydrolysis, Biochim. Biophys. Acta 321:189.PubMedGoogle Scholar
  61. Lichtenstein, E. P., and Fuhreman, T. W., 1971, Activity of an NADPH-dependent nitroreductase in houseflies, Science 172:589.PubMedGoogle Scholar
  62. Lichtenstein, E. P., and Schulz, K. R., 1964, The effects of moisture and microorganisms on the persistence and metabolism of some organophosphorus insecticides in soils with special emphasis on parathion, J. Econ. Entomol. 57:618.Google Scholar
  63. Main, A. R., 1960a, The purification of the enzyme hydrolysing diethyl p-nitrophenyl phosphate (paraoxon) in sheep serum, Biochem. J. 74:10.PubMedGoogle Scholar
  64. Main, A. R., 1960, The differentiation of the A-type esterases in sheep serum, Biochem. J. 75:188.PubMedGoogle Scholar
  65. Main, A. R., and Braid, P. E., 1962, Hydrolysis of malathion by aliesterases in vitro and in vivo, Biochem. J. 84:255.PubMedGoogle Scholar
  66. Main, A. R., and Dauterman, W. C., 1967, Kinetics for the inhibition of carboxylesterase by malaoxon, Can. J. Biochem. 45:757.PubMedGoogle Scholar
  67. Matsumura, F., and Boush, G. M., 1966, Malathion degradation by Trichoderma viride and a Pseudomonas species, Science 153:1278.PubMedGoogle Scholar
  68. Matsumura, F., and Brown, A. W. A., 1963, Studies on carboxyesterase in malathion-resistant Culex tarsalis, J. Econ. Entomol. 56:381.Google Scholar
  69. Matsumura, F., and Hogendijk, C. J., 1964, The enzymatic degradation of parathion in organophosphate-susceptible and-resistant houseflies, J. Agr. Food Chem. 12:447.Google Scholar
  70. Matsumura, F., and Voss, G., 1965, Properties of partially purified malathion carboxylesterase of the two-spotted spider mite, J. insect Physiol. 11:147.PubMedGoogle Scholar
  71. Matsumura, F., and Ward, C. T., 1966, Degradation of insecticides by the human and the rat liver, Arch. Environ. Health 13:257.PubMedGoogle Scholar
  72. Matthews, H. B., and McKinney, J. D., 1974, Dieldrin metabolism to cis-dihydroaldrindiol and epimerization of cis to trans dihydroaldrindiol by rat liver microsomes, Drug Metab. Disp. 2:333.Google Scholar
  73. Mazur, A., 1946, An enzyme in animal tissues capable of hydrolyzing the phosphorus-fluorine bond of alkyl fluorophosphates, J. Biol. Chem. 164:271.PubMedGoogle Scholar
  74. Menn, J. J., and M. Beroza (eds.), 1972, Insect Juvenile Hormones: Chemistry and Action, Academic Press, New York.Google Scholar
  75. Mick, D. L., and Dahm, P. A., 1970, Metabolism of parathion by two species of Rhizobium, J. Econ. Entomol. 63:1155.PubMedGoogle Scholar
  76. Motoyama, N., and Dauterman, W. G, 1974, The role of non-microsomal metabolism in organophosphorus resistance, J. Agr. Food Chem. 22:350.Google Scholar
  77. Mounter, L. A., 1955, The complex nature of dialkylfluorophosphatases of hog and rat liver and kidney, J. Biol. Chem. 215:705.PubMedGoogle Scholar
  78. Mounter, L. A., and Chanutin, A., 1954, Dialkylfluorophosphatase of kidney. III. Studies of activation and inhibition of cofactors, J. Biol. Chem. 210:219.PubMedGoogle Scholar
  79. Mounter, L. A., Baxter, R. F., and Chanutin, A., 1955a, Dialkylfluorophosphatases of microorganisms, J. Biol. Chem. 215:699.PubMedGoogle Scholar
  80. Mounter, L. A., Dien, L. T. H., and Chanutin, A., 1955b, The distribution of dialkylfuoro phosphatase in the tissue of various species, J. Biol. Chem. 215:691.PubMedGoogle Scholar
  81. Murphy, S. D., and DuBois, K. P., 1957, Quantitative measurement of inhibition of the enzymatic detoxification of malathion by EPN (ethyl p-nitrophenyl thionobenzenephosphonate), Proc. Soc. Expl. Biol. Med. 96:813.Google Scholar
  82. Nakatsugawa, T., Tolman, N. M., and Dahm, P. A., 1969, Metabolism of S35-parathion in the housefly, J. Econ. Entomol. 62:408.PubMedGoogle Scholar
  83. Nishizawa, Y., and Casida, J. E., 1965, Synthesis of d-trans-chrysanthemumic acid-l-14C and its antipode on a semimicro scale. J. Agr. Food Chem. 13:525.Google Scholar
  84. Nolan, J., and O’Brien, R. D., 1970, Biochemistry of resistance to paraoxon in strains of houseflies, J. Agr. Food Chem. 18:802.Google Scholar
  85. O’Brien, R. D., 1957, Properties and metabolism in the cockroach and mouse of malathion and malaoxon, J. Econ. Entomol. 50:159.Google Scholar
  86. O’Brien, R. D., 1960, Toxic Phosphorus Esters, Academic Press, New York.Google Scholar
  87. O’Brien, R. D., Thorn, G. D., and Fisher, R. W., 1958, New organophosphate insecticides developed on rational principles, J. Econ. Entomol. 51:714.Google Scholar
  88. Oesch, F., 1973, Mammalian epoxide hydrases: Inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds, Xenobiotica 3:305.PubMedGoogle Scholar
  89. Oesch, F., 1974, Purification and specificity of a human microsomal epoxide hydratese, Biochem. J. 139:77.PubMedGoogle Scholar
  90. Oesch, F., and Daly, J., 1971, Solubilization, purification and properties of a hepatic epoxide hydrase. Biochim. Biophys. Acta 227:692.PubMedGoogle Scholar
  91. Oesch, F., Jerina, D. M., and Daly, J. W., 1971, A radiometric assay for hepatic epoxide hydrase activity with (7-3H) styrene oxide. Biochim. Biophys. Acta 227:685.PubMedGoogle Scholar
  92. Oesch, F., Jerina, D. M., Daly, J., and Rice, J., 1973, Induction, activation and inhibition of epoxide hydrase: An anomalous prevention of chlorobenzene-induced hepatotoxicity by an inhibitor of epoxide hydrase, Chem.-Biol. Interact. 6:189.PubMedGoogle Scholar
  93. Oesch, F., Thoenen, H., and Fahrländer, H., with technical assistance of Suda, K., 1974, Epoxide hydrase in human liver biopsy specimens: Assay and properties. Biochem. Pharmacol. 23:1307.PubMedGoogle Scholar
  94. Oonnithan, E. S., and Miskus, R., 1964, Metabolism of dieldrin C14 by dieldrin-resistant Culex pipens quinquefasciatus mosquitoes, J. Econ. Entmol. 57:425.Google Scholar
  95. Pankaskie, J. E., Fountaine, F. C., and Dahm, P. A., 1952, The degradation and detoxification of parathion in dairy cows, J. Econ. Entomol. 45:51.Google Scholar
  96. Plapp, F. W., Jr., and Tong, H. H. C., 1966, Synergism of malathion and parathion against resistant insects: Phosphorus esters with synergistic properties, J. Econ. Entomol. 59:11.PubMedGoogle Scholar
  97. Plapp, F. W., Jr., and Valega, T. M., 1967, Synergism of carbamate and organophosphate insecticides by noninsecticidal carbamates, J. Econ. Entomol. 60:1094.Google Scholar
  98. Plapp, F. W., Jr., Bigley, W. S., Chapman, G. A., and Eddy, G. W., 1963, Synergism of malathion against resistant houseflies and mosquitoes, J. Econ. Entomol. 56:643.Google Scholar
  99. Rose, H. A., and Young, R. G., 1973, Nitroreductases in the Madagascar cockroach, Gromphadorhina portentosa, Pestic. Biochem. Physiol. 3:243.Google Scholar
  100. Satyanarayana, T., and Getzin, L. W., 1973, Properties of a stable cell-free esterase from soil, Biochemistry 12:1566.PubMedGoogle Scholar
  101. Seume, F. W., and O’Brien, R. D., 1960a, Metabolism of malathion by rat liver tissue preparations and its modification by EPN, J. Agr. Chem. 8:36.Google Scholar
  102. Seume, F. W., and O’Brien, R. D., 1960, Potentiation of the toxicity to insects and mice of phosphorothionates containing carboxyester and carboxyamide groups, Toxicol. Appl. Pharmacol. 2:495.PubMedGoogle Scholar
  103. Shishido, T., and Fukami, J., 1972, Enzymatic hydrolysis of diazoxon by rat tissue homogenates, Pestic. Biochem. Physiol. 2:39.Google Scholar
  104. Škrinjarić-Špoljar, M., and Reiner, E., 1968, Hydrolysis of diethyl-p-nitrophenyl phosphate and ethyl-p-nitrophenyl-ethyl phosphonate by human sera, Biochim. Biophys. Acta 165:289.PubMedGoogle Scholar
  105. Slade, M., and Wilkinson, C. F., 1973, Juvenile hormone analogs: A possible case of mistaken identity? Science 181:672.PubMedGoogle Scholar
  106. Slade, M., and Zibitt, C. H., 1972, Metabolism of Cecropia juvenile hormone in insects and in mammals, In: Insect Juvenile Hormones: Chemistry and Action (J. J. Menn and M. Beroza, eds.), P. 155, Academic Press, New York.Google Scholar
  107. Slade, M., Brooks, G. T., Hetnarski, H. K., and Wilkinson, C. F., 1975, Inhibition of the enzymatic hydration of the epoxide HEOM in insects, Pestic. Biochem. Physiol 5:35.Google Scholar
  108. Stoming, T. A., and Bresnick, E., 1973, Gas Chromatographie assay of epoxide hydrase activity with 3-methylcholanthrene-11-12-oxide, Science 181:951.PubMedGoogle Scholar
  109. Stoming, T. A., and Bresnick, E., 1974, Hepatic epoxide hydrase in neonatal and partially hepatectomized rats, Cancer Res. 34:2810.PubMedGoogle Scholar
  110. Tomlin, A. D., 1968, Trans-aldrin glycol as a metabolite of dieldrin in larvae of the southern house mosquito, J. Econ. Entomol 61:855.Google Scholar
  111. Uchida, T., and O’Brien, R. D., 1967, Dimethoate degradation by human liver and its significance for acute toxicity, Toxicol Appl Pharmacol 10:89.PubMedGoogle Scholar
  112. Uchida, T., Dauterman, W. C., and O’Brien, R. D., 1964, The metabolism of dimethoate by vertebrate tissues, J. Agr. Food Chem. 12:48.Google Scholar
  113. Uchida, T., Zschintzsch, J., and O’Brien, R. D., 1966, Relation between synergism and metabolism of dimethoate in mammals and insects, Toxicol. Appl. Pharmacol. 8:259.PubMedGoogle Scholar
  114. Welling, W., and Blaakmeer, P. T., 1971, Metabolism of malathion in a resistant and susceptible strain of houseflies: Insecticide resistance, synergism, enzyme induction, in: Proceedings of the Second International IUPAC Congress of Pesticide Chemistry, Vol. II (A. S. Tahori, ed.), pp. 61–75, Gordon and Breach, New York.Google Scholar
  115. Welling, W., Blaakmeer, P., Vink, G. J., and Voerman, S., 1971, In vitro hydrolysis of paraoxon by parathion resistant houseflies, Pestic. Biochem. Physiol. 1:61.Google Scholar
  116. White, A. F., 1972, Metabolism of the juvenile hormone analogue methyl farnesoate 10,11-epoxide in two insect species, Life Sci. 11:201.Google Scholar
  117. Winteringham, F. P. W., Harrison, A., and Bridges, P. M., 1955, Absorption and metabolism of [14C] pyrethroids by the adult housefly, Musca domestica L., Biochem. J. 61:359.PubMedGoogle Scholar
  118. Yamamoto, I., and Casida, J. E., 1966, O-Demethyl pyrethrin II analogs from oxidation of pyrethrin I, allethrin, dimethrin and phthalthrin by housefly enzyme system, J. Econ. Entomol. 59:1542.Google Scholar
  119. Yamamoto, I., and Casida, J. E., 1968, Synthesis of 14C-labelled pyrethrin I, allethrin, phthalthrin, and dimethrin on a submillimole scale, Agr. Biol. Chem. 32:1382.Google Scholar
  120. Yamamoto, I., Kimmel, E. C., and Casida, J. E., 1969, Oxidative metabolism of pyrethroids in houseflies, J. Agr. Food Chem. 17:1227.Google Scholar
  121. Young, R. G., 1975, Flavin-linked azoreductases of the Madagascar cockroach, Gromphadorhina portentosa, Insect. Biochem. 5:in press.Google Scholar
  122. Zeid, M. M. I., Dahm, P. A., Hein, R. E., and McFarland, R. H., 1953, Tissue distribution, excretion of 14CO2 and degradation of radioactive pyrethrins administered to the American cockroach, J. Econ. Entomol. 46:324.Google Scholar

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© Springer Science+Business Media New York 1976

Authors and Affiliations

  • W. C. Dauterman
    • 1
  1. 1.Department of EntomologyNorth Carolina State UniversityRaleighUSA

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