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Xenobiotica
the fate of foreign compounds in biological systems
Volume 16, 1986 - Issue 10-11
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Original Article

Insecticide metabolism and selective toxicity

Pages 989-1002 | Published online: 30 Sep 2009

References

  • Abdel-Aal Y. A. I., Hammock B. D. 3-Octylthio-1,1,1-trifluoro-2-propanone, a high affinity and show binding inhibitor of juvenile hormone esterase from Trichoplusia Ni (Hubner). Insect Biochemistry 1985; 15: 111–122
  • Aldridge W. N., Verschoyle R. D., Peal J. A. O, S, S-Trimethyl phosphorodithioate and O, O, S-triethyl phosphorothioate: pharmacokinetics in rats and effect of pretreatment with compounds affecting the drug processing systems. Pesticide Biochemistry and Physiology 1984; 21: 265–274
  • Ariens E. J. Stereoselectivity of bioactive agents: general aspects. Stereochemistry and Biological Activity of Drugs, E. J. Ariens, W. Soudijn, P. B. Timmermans. Blackwell, Oxford 1983; 11–32
  • Baker E. L., Jr, Warren M., Zack M., Dobbin R. D., Miles J. W., Miller S., Alderman L., Teeters W. R. Epidemic malathion poisoning in Pakistan malaria workers. Lancet 1978, 1: 31–33
  • Benson W. H., Dorough H. W. Comparative ester hydrolysis of carbaryl and ethiofencarb in four mammalian species. Pesticide Biochemistry and Physiology 1984; 21: 199–206
  • Bigley W. S., Vinson S. B. Effects of piperonyl butoxide and DEF on the metabolism of methoprene by the imported fire ant, Solenopsis invicta Buren. Pesticide Biochemistry and Physiology 1979; 10: 14–22
  • Bowers W. S., Ohta T., Cleere J. S., Marsella P. A. Discovery of insect anti-juvenile hormones in plants. Science 1976; 193: 542–547
  • Bowers W. S., Evans P. H., Marsella P. A., Soderlund D. M., Bettarini F. Natural and synthetic allatotoxins: suicide substrates for juvenile hormone biosynthesis. Science 1982; 217: 647–648
  • Brattsten L. B., Metcalf R. L. Age-dependent variations in the response of several species of diptera to insecticidal chemicals. Pesticide Biochemistry and Physiology 1973; 3: 189–198
  • Brooks G. T. Chlorinated Insecticides, Vol. II. CRC Press, Cleveland 1974; 123–126
  • Brooks G. T. Selective toxicity of insecticides. The Future for Insecticides, Needs and Prospects, R. L. Metcalf, J. J. McKelvey, Jr. John Wiley, New York 1976; 97–139
  • Brooks G. T. The metabolism of xenobiotics in insects. Progress in Drug Metabolism, Vol. 3, J. W. Bridges, L. F. Chasseaud. John Wiley, Chichester 1979; 151–214
  • Brooks G. T. Metabolism and pesticide design. Progress in Drug Metabolism, Vol. 8, J. W. Bridges, L. F. Chasseaud. Taylor & Francis, London 1984; 101–202
  • Brooks G. T., Hamnett A. F., Jennings R. C., Ottridge A. P., Pratt G. E. (1979a) Aspects of the mode of action of precocenes on milkweed bugs (Oncopeltus fasciatus) and Locusts (Locusta migratoria). Proceedings of the 1979 British Crop Protection Conference—Pests and Diseases. 1979. 1: 273–279
  • Brooks G. T., Pratt G. E., Jennings R. C. The action of precocenes in milkweed bugs (Oncopeltus fasciatus) and locusts (Locusta migratoria). Nature 1979b; 281: 570–572
  • Brooks G. T., Ottridge A. P., Jennings R. C., Mace D. W., Alexander B. A. The effect of 2,2-dimethylchromene derivatives and some other compounds on the development of Oncopeltus fasciatus (Dallas) and Locusta migratoria migratorioides (R & F). Pesticide Science 1985; 16: 571–588
  • Brown M. A., Casida J. E. Influence of pyrethroid ester, oxime ether and other central linkages on insecticidal activity, hydrolytic detoxification and physicochemical parameters. Pesticide Biochemistry and Physiology 1984; 22: 78–85
  • Bull D. L. Fate and efficacy of acephate after application to plants and insects. Journal of Agricultural and Food Chemistry 1979; 27: 268–272
  • Casida J. E. Mixed function oxidase involvement in the biochemistry of insecticide synergists. Journal of Agricultural and Food Chemistry 1970; 18: 753–772
  • Casida J. E. Novel aspects of metabolism of pyrethroids. Pesticide Chemistry: Human Welfare and the Environment, J. Miyamoto, P. C. Kearney. Pergamon Press, Oxford 1983; 2: 187–192
  • Casida J. E., Gaughan L. C., Ruzo L. O. Comparative metabolism of pyrethroids derived from 3-phenoxybenzyl and α-cyano-3-phenoxybenzyl alcohols. Advances in Pesticide Science, H. Geissbuhler, G. T. Brooks, P. C. Kearney. Pergamon Press, Oxford 1979; 182–189
  • Clark A. G., Shamaan N. A. Evidence that DDT-dehydrochlorinase from the house fly is a glutathione S-transferase. Pesticide Biochemistry and Physiology 1984; 22: 249–261
  • Coats J. R. Structure-activity relationships in DDT-analogs. Insecticide Mode of Action, J. R. Coats. Academic Press, New York 1982; 29–41
  • Coats J. R., Metcalf R. L., Kapoor I. P. Effective DDT analogues with altered aliphatic moieties. Isobutanes and chloropropanes. Journal of Agricultural and Food Chemistry 1977; 25: 859–868
  • Coats J. R., Metcalf R. L., Kapoor I. P., Chio L., Boyle P. A. Physical-chemical and biological degradation studies on DDT analogues with altered aliphatic moieties. Journal of Agricultural and Food Chemistry 1979; 27: 1016–1022
  • Devonshire A. L., Moores G. D. A carboxylesterase with broad substrate specificity causes organophosphorus, carbamate and pyrethroid resistance in peach-potato aphids (Myzus persicae). Pesticide Biochemistry and Physiology 1982; 18: 235–246
  • Drabek J., Fluck V. Synthesis and properties of O-aryl O-alkyl S-alkyl phosphorothioates. Advances in Pesticide Science, H. Geissbuhler, G. T. Brooks, P. C. Kearney. Pergamon Press, Oxford 1979; 130–134
  • Dutton F. E., Gemrich E. G., II, Lee B. L., Nelson S. G., Parham P. H., Seaman W. J. Insecticidal phosphorinanylaminothio derivatives of the carbamate methomyl. Journal of Agricultural and Food Chemistry 1981; 29: 1114–1118
  • Elliott M. Synthetic pyrethroids. Synthetic pyrethroids, M. Elliott. ACS Symposium Series No. 42, American Chemical Society, Washington, D.C. 1977; 1–28
  • Fahmy M. A., Fukuto T. R. Rationale and chemistry of proinsecticidal methylcarbamates. Pesticide Chemistry: Human Welfare and Environment, Vol. 1, J. Miyamoto, P. C. Kearney. Pergamon Press, Oxford 1983; 193–200
  • Fahmy M. A. H., Mallipudi N. M., Fukuto T. R. Selective toxicity of N, N'-thiodicarbamates. Journal of Agricultural and Food Chemistry 1978; 26: 550–557
  • Farooqui M. Y. H., Metcalf R. L. Comparative metabolism of six ethoxychlor analogs and DDT in DDT-resistant and susceptible strains of the house fly Musca domestica L. Pesticide Biochemistry and Physiology 1983; 19: 210–220
  • Fridman-Cohen S., Staal G. B., Pener M. P. Quantitative studies on anti-allatin and lethal effects of a synthetic precocene in different larval instars of the desert locust. Entomologia experimentalis et applicata 1984; 36: 115–124
  • Fukuto T. R. Carbamate insecticides. The Future for Insecticides, Needs and Prospects, R. L. Metcalf, J. J. McKelvey, Jr. John Wiley, New York 1976; 313–346
  • Fukuto T. R. Structure-activity relationships in derivatives of anticholinesterase insecticides. Pesticide Chemistry: Human Welfare and the Environment, Vol. 1, J. Miyamoto, P. C. Kearney. Pergamon Press, Oxford 1983; 203–212
  • Gray A. J., Fukuto T. R. Metabolism of O, O, S-trimethyl phosphorothioate in rats after oral administration of a toxic dose, and the effect of coadministration of its antagonistic thionate isomer. Pesticide Biochemistry and Physiology 1984; 22: 295–311
  • Hirashima A., Leader H., Holden I., Casida J. E. Resolution and stereoselective action of sulprofos and related S-propyl phosphorothiolates. Journal of Agricultural and Food Chemistry 1984; 32: 1302–1307
  • Holan G., Johnson W. M. P., O'Keefe D. F., Rihs K., Smith D. R. J., Virgona C. T., Walser R., Haslam J. M. New aryl-poly fluorocyclobutane insecticides. Chemical and biological studies. Pesticide Chemistry, Vol. 1, J. Miyamoto, P. C. Kearney. Pergamon Press, Oxford 1983; 119–124
  • Imamura T., Hasegawa L. Effects of an impurity on malathion and its structural analog on rat liver carboxylesterases and erythrocyte esterases. Pesticide Biochemistry and Physiology 1984; 22: 312–320
  • Ishaaya I., Casida J. E. Pyrethroid esterases may contribute to natural pyrethroid tolerance of larvae of the Common Green Lacewing. Environmental Entomology 1981; 10: 681–684
  • Ishaaya I., Casida J. E. Pyrethroid detoxification and synergism in insects. Pesticide Chemistry: Human Welfare and the Environment, Vol. 3, J. Miyamoto, P. C. Kearney. Pergamon Press, Oxford 1983; 307–310
  • Jojima T., Fahmy M. A. H., Fukuto T. R. Sugar, glyceryl, and (pyridylalkoxy)sulfinyl derivatives of methylcarbamate insecticides. Journal of Agricultural and Food Chemistry 1983; 31: 613–620
  • Kabachnik M. I., Mastryukova T. A. Synthesis and selectivity of action of some new thiophosphoro-organic insecticides. Advances in Pesticide Science, H. Geissbuhler, G. T. Brooks, P. C. Kearney. Pergamon Press, Oxford 1979; 120–129
  • Kaneko H., Matsuo M., Miyamoto J. Comparative metabolism of stereoisomers of cyphenothrin and phenothrin isomers in rats. Journal of Pesticide Science 1984; 9: 237–247
  • Kao T. S., Fukuto T. R. Metabolism of O, S-dimethyl propionyl- and hexanoylphosph-oramidothioate in the housefly and white mouse. Pesticide Biochemistry and Physiology 1977; 7: 83–95
  • Kimura S., Toeda K., Miyamoto T., Yamamoto I. Activation and detoxication of S-alkyl phosphorothiolate insecticides. Journal of Pesticide Science 1984; 9: 137–142
  • Kuhr R. J., Dorough H. W. Carbamate Insecticides: Chemistry, Biochemistry and Toxicology. CRC Press, Cleveland 1976
  • Lee A., Metcalf R. L., Williams J. W., Hirwe A. S., Sanborn J. R., Coats J. R., Fukuto T. R. Structure-activity correlations of the insecticide prolan and its analogs. Pesticide Biochemistry and Physiology 1977; 7: 426–436
  • Lee P. W., Allahayari R., Fukuto T. R. Studies on chiral isomers of fonofos and fonofos oxon, III. In vivo metabolism. Pesticide Biochemistry and Physiology 1978; 9: 23–32
  • Lee P. W., Allahyari R., Fukuto T. R. Absorption and metabolism of the chiral isomers of fonofos in the corn and cotton plant. Journal of Environmental Science and Health 1980; B15: 25–37
  • Lin P. T., Main A. R., Tucker W. P., Motoyama N., Dauterman W. C. Studies on organophosporus impurities in technical malathion: inhibition of carboxylesterases and the stability of isomalathion. Pesticide Biochemistry and Physiology 1984; 21: 223–231
  • Mackness M. I., Walker C. H., Brealey C. J., Lewis C. N. A. (1984) ‘A’-esterases as a factor in the selective toxicity of insecticides. Proceedings of the 1984 British Crop Protection Conference—Pests and Diseases. 1984. 3: 875–880
  • Mallipudi N. M., Fukuto T. R. Toxicity of N-sulfenylated derivatives of insecticidal methylcarbamate esters to the honeybee. Journal of Agricultural and Food Chemistry 1979; 27: 261–265
  • Marsden P. J., Kuwano E., Fukuto T. R. Metabolism of carbosulfan in the rat and house fly. Pesticide Biochemistry and Physiology 1982; 18: 38–48
  • Metcalf R. L. Organochlorine insecticides, survey and prospects. The Future for Insecticides, R. L. Metcalf, J. J. McKelvey, Jr. John Wiley, New York 1976; 223–285
  • Metcalf R. A., Metcalf R. L. Selective toxicity of analogs of methyl parathion. Pesticide Biochemistry and Physiology 1973; 3: 149–159
  • Miyamoto J., Ohkawa K. Oxidative processes in pesticide transformation. Advances in Pesticides Science, H. Geissbuhler, G. T. Brooks, P. C. Kearney. Pergamon Press, Oxford 1979; 508–515
  • O'Brien R. D. Insecticides: Action and Metabolism. Academic Press, New York 1967
  • Ohkawa H. Stereoselectivity of organophosphorus insecticides. Insecticide Mode of Action, J. R. Coats. Academic Press, New York 1982; 163–185
  • Pratt G. E., Jennings R. C., Hamnett A. F., Brooks G. T. Lethal metabolism of precocene I to a reactive epoxide by locust corpora allata. Nature 1980; 284: 320–323
  • Rose R. L., Sparks T. C. Acephate toxicity, metabolism, and anticholinesterase activity in Heliothis virescens (F.) and Anthonomus grandis grandis (Boheman). Pesticide Biochemistry and Physiology 1984; 22: 69–77
  • Ryan D. L., Fukuto T. R. The effect of isomalathion and O, S, S-trimethyl phosphorodithioate on the in vivo metabolism of malathion in rats. Pesticide Biochemistry and Physiology 1984; 21: 349–357
  • Soderlund D. M., Casida J. E. Pharmacokinetics of cis-and trans-substituted pyrethroids in the American Cockroach. Synthetic Pyrethroids, M. Elliott. ACS Symposium Series No. 42, American Chemical Society, Washington, D.C. 1977a; 162–172
  • Soderlund D. M., Casida J. E. Stereospecificity of pyrethroid metabolism in mammals. Synthetic Pyrethroids, M. Elliott. ACS Symposium Series No. 42, American Chemical Society, Washington, D.C. 1977b; 173–185
  • Soderlund D. M., Hessney C. W., Helmuth D. W. Pharmacokinetics of cis- and trans-substituted pyrethroids in the American Cockroach. Pesticide Biochemistry and Physiology 1983a; 20: 161–168
  • Soderlund D. M., Sanborn J. R., Lee P. W. Metabolism of pyrethrins and pyrethroids in insects. Progress in Pesticide Biochemistry and Toxicology, Vol. 3, D. A. Hutson, T. R. Roberts. John Wiley, Chichester 1983b; 401–435
  • Solomon K. R., Metcalf R. L. The effect of piperonyl butoxide and triorthocresyl phosphate on the activity and metabolism of Altosid in Tenebrio molitor L. and Oncopeltus fasciatus (Dallas). Pesticide Biochemistry and Physiology 1974; 4: 127–134
  • Talcott R. E., Denk H., Mallipudi N. M. Malathion carboxylesterase activity in human liver and its inactivation by isomalathion. Toxicology and Applied Pharmacology 1979; 49: 373–376
  • Thompson C. M., Fukuto T. R. Mechanism of cholinesterase inhibition by methamidophos. Journal of Agriculture and Food Chemistry 1982; 30: 282–284
  • Umetsu N. Studies on the selectively toxic derivatives of methylcarbamate insecticides. Journal of Pesticide Science 1984; 9: 169–180
  • Umetsu N., Mallipudi N. M., Toia R. F., March R. B., Fukuto T. R. Toxicological properties of phosphorothioate and related esters present as impurities in technical organophosphorus insectides. Journal of Toxicology and Environmental Health 1981; 7: 481–497
  • Umetsu N., Toia R. F., Mallipudi N. M., March R. B., Fukuto T. R. A novel antagonistic effect to the toxicity in the rat of O, O, S-trimethyl phosphorothioate by its phosphorothionate isomer. Journal of Agricultural and Food Chemistry 1979; 27: 1423–1425
  • Welling W., de Vries J. W., Paterson G. D., Duffy M. R. Toxicodynamics of malathion in houseflies. Pesticide Biochemistry and Physiology 1983; 20: 360–372
  • Welling W., de Vries J. W., Voerman S. Oxidative cleavage of a carboxyester bond as a mechanism of resistance to malaoxon in houseflies. Pesticide Biochemistry and Physiology 1974; 4: 31–43
  • Wilkinson C. F. Insecticide synergism. The Future for Insecticides: Needs and Prospects, R. L. Metcalf, J. J. McKelvey, Jr. John Wiley, New York 1976; 195–222
  • Wing K. D., Glickman A. H., Casida J. E. Phosphorothiolate pesticides and related compounds: oxidative bioactivation and aging of the inhibited acetylcholinesterase. Pesticide Biochemistry and Physiology 1984; 21: 22–30

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