The Metabolism Of Pesticidal Carbamates

References

• Benson WR. The chemistry of pesticides. Ann. N. Y. Acad. Sci. 1969; 160: 7
   PubMedGoogle Scholar
• Holly K. Structure, activity and selectivity: a survey of present-day herbicides. Proc. 9th Brit. Weed Control Conf. 1968; 3: 1285
   Google Scholar
• O'Brien RD. insecticides. Action and Metabolism. Academic Press, New York 1967; 83
   Google Scholar
• Williams RT. Detoxication Mechanisms2nd ed. Chapman and Hall Ltd., London 1959
   Google Scholar
• Brodie B. B., Maickel RP. Comparative biochemistry of drug metabolism. Metabolic Factors Controlling Duration of Drug Action, B. B. Brodie, E. G. Erdos. MacMillan (Pergamon), New York 1962; 299
   Google Scholar
• Miller E. C., Miller JA. Mechanisms of chemical carcinogenesis: nature of proximate carcinogens and interactions with macromole.cules. Pharmacol. Rev. 1966; 18: 805
   PubMed Web of Science ®Google Scholar
• Gillett JR. Biochemistry of drug oxidation and reduction by enzymes in hepatic endoplasmic reticulum. Ann. Rev. Pharmacol 1966; 4: 219
   Google Scholar
• Davison AN. The conversion of schradan (OMPA) and parathion into inhibitors of cholinesterase by mammalian liver. Biochem. J. 1955; 61: 203
   PubMed Web of Science ®Google Scholar
• Palade E. S., Siekevitz P. Liver microsomes. An integrated morphological and biochemical study. J. Biophys. Biochem. Cyt. 1956; 2: 171
   PubMedGoogle Scholar
• Fouts JR. Interaction of drugs and hepatic microsomes. Fed. Proc 1962; 21: 1107
   PubMedGoogle Scholar
• Gram T. E., Fouts JR. Studies on the intra-microsomal distribution of hepatic enzymes which catalyse the metabolism of drugs and other foreign compounds. Enzymatic Oxidation of Toxicants, E. Hodgson. North Carolina State University. 1968; 47
   Google Scholar
• Williams RT. Detoxication mechanisms in mail. Clin. Pharmacol. Titer. 1963; 4: 234
   PubMed Web of Science ®Google Scholar
• Williams RT. Drug metabolism in man as compared with laboratory animals. Proc. European Society for the Study of Drug Toxicity 1964; 4: 9
   Google Scholar
• Williams RT. Patterns of excretion of drugs in man and other species. Drug Responses in Man, G. Wolstenholme, R. Porter. J. and A. Churchill, London 1967; 71
   Google Scholar
• Gillette JR. Oxidation and reduction by microsomal enzymes. Metabolic Factors Controlling Duration of Drug Action, B. B. Brodie, E. G. Erdos. MacMillan (Pergamon), New York 1962; 13
   Google Scholar
• Gillette IR. Metabolism of drugs and other foreign compounds by enzymatic mechanisms. Fortschr. Arzneimittelforsch. 1963; 6: 13
   Google Scholar
• Gillette JR. Individually different responses to drugs according to age, sex and functional or pathological state. Drug Responses in Man, G. Wolstenholme, R. Porter. J. and A. Churchill, London 1967; 24
   Google Scholar
• Gillette JR. Significance of mixed oxygenases and nitroreductase in drug metabolism. Ann. N. Y. Acad. Sci. 1969; 160: 558
   PubMed Web of Science ®Google Scholar
• Fouts IR. Factors influencing the metabolism of drugs in liver microsomes. Ann. N. Y. Acad. Sci. 1963; 104: 875
   Web of Science ®Google Scholar
• Remmer H. The fate of drugs in the organism. Ann. Rev. Pharmacol. 1965; 5: 405
   PubMedGoogle Scholar
• Shuster L. Metabolism of drugs and toxic substances. Ann. Rev. Biochem. 1964; 33: 571
   PubMed Web of Science ®Google Scholar
• Parke DV. The Biochemistry of Foreign Compounds. Pergamon, London 1968
   Google Scholar
• Boyland E., Chasseaud LF. The role of glutathione and giutathione-S-transferases in mercapturic acid biosynthesis. Advances Enzym. 1969; 32: 173
   PubMedGoogle Scholar
• Mellet LB. Comparative drug metabolism. Fortschr. Arzneimittelforsch. 1969; 13: 136
   Google Scholar
• Hayaishi O. Oxygenases. Academic Press, New York 1962; 1
   Google Scholar
• Hayaishi O. Enzymic hydroxylation. Ann. Rev. Biochem. 1969; 38: 21
   PubMed Web of Science ®Google Scholar
• Oonnithan E. S., Casida JE. Oxidation of methyl and dimethyl insecticide chemicals by microsomal enzymes and anticholinesterase activity of the metabolites. J. Agr. Food Chem. 1968; 16: 28
   Web of Science ®Google Scholar
• Balba M. H., Casida JE. Synthesis of possible metabolites of methylcarbamate insecticide chemicals. Hydroxyaryl and hydroxyalkylphenyi methylcarbamates. J. Agr. Food Chem. 1968; 16: 562
   Web of Science ®Google Scholar
• Leeling N. C., Casida JE. Metabolites of carbaryl (l-naphthyl-N-methylcarbamate) in mammals and enzymatic systems for their formation. J. Agr. Food Chem. 1966; 14: 281
   Web of Science ®Google Scholar
• Jerina D. M., Daly J. W., Witkop B, Zaltzmann-Nirenberg P., Udenfrierid S. The role of arene oxide -oxepin systems in the metabolism of aromatic substrates - III. Formation of 1,2-naphthalene oxide from naphthalene by liver microsomes,/. Amer. Chem. Soc 1968; 96: 6525
   Google Scholar
• Lykken L., Casida JE. Metabolism of organic insecticide chemicals. Canad. Med. Ass. J. 1969; 100: 145
   PubMed Web of Science ®Google Scholar
• Metcalf R. L., Fukuto T. R., Collins C, Bork K., Abd-El-Aziz S., Munoz R., Cassil CC. Metabolism of 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-N-methylcarbamate (Furadan) in plants, insects and mammals. J. Agr. Food Chem 1968; 16: 300
   Web of Science ®Google Scholar
• Dorough HW. Metabolism of furadan (NIA-10242) in rats and houseflies. J. Agr. Food Chem. 1968; 16: 319
   Web of Science ®Google Scholar
• Ivie G. W., Dorough HW. Furadan-14C metabolism in a lactating cow. J. Agr. Food Chem. 1968; 16: 849
   Web of Science ®Google Scholar
• McMahon RE. Microsomal dealkylation of drugs. Substrate specificity and mechanism. J. Pharm. Set 1966; 55: 457
   Web of Science ®Google Scholar
• Hodgson E., Casida JE. Metabolism of N,N-dialkylcarbamates and related compounds by rat liver. Biochem. Pharmacol 1961; 8: 179
   PubMed Web of Science ®Google Scholar
• Hodgson E., Casida JE. Biological oxidation of N, N-dialkylcarbamates. Biochem. Biophys. Acta 1960; 42: 184
   PubMed Web of Science ®Google Scholar
• Dorough H. W., Leeling NC., Casida JE. Nonhydrolytic pathway in metabolism of N-methylcarbamate insecticides. Science (N. Y.) 1963; 140: 170
   PubMed Web of Science ®Google Scholar
• Dorough H. W., Casida JE. Nature of certain metabolites of the insecticide Sevin. J. Agr. Food Chem. 1964; 12: 294
   Web of Science ®Google Scholar
• Axelrod J. The enzymic cleavage of aromatic ethers. Biochem. J. 1956; 63: 634
   PubMed Web of Science ®Google Scholar
• Mazel P., Henderson J. R., Axelrod J. S-demethylation by microsomal enzymes. J. Pharm. Exp. Ther. 1964; 143: 1
   PubMed Web of Science ®Google Scholar
• Andrawes N. R., Dorough H. W., Lindquist DA. Degradation and elimination of Temik in rats. J. Econ. Entom. 1967; 60: 979
   PubMed Web of Science ®Google Scholar
• Dorough H. W., Ivie GW. Temik-35S metabolism in a lactating cow. J. Agr. Food Chem. 1968; 16: 460
   Web of Science ®Google Scholar
• Knaak J. B., Tallant M. J., Sullivan LJ. The metabolism of 2-methyl-2-(methylthio)-propionaldehyde O-(methylcarbamoyl) oxime in the rat. J. Agr. Food Chem. 1966; 14: 573
   Web of Science ®Google Scholar
• Krishna J. G., Casida IE. Fate in rats of the radiocarbon from ten variously labelled methyl and dimethyl-carbamate-14C insecticide chemicals and their hydrolysis products. J. Agr. Food Chem. 1966; 14: 98
   Web of Science ®Google Scholar
• Baron R. L., Doherty JD. Metabolism and excretion of an insecticide (6-chloro-3,4-dimethylphenyl-N-methylcarbamate) in the rat. J. Agr. Food Chem. 1967; 15: 830
   Web of Science ®Google Scholar
• Robbins J. D., Bakke J. E., Feil VJ. Metabolism of 4-benzothienyl-N-methylcarbamate (Mobam) in rats. Balance study and urinary metabolites. J. Agr. Food Chem. 1969; 17: 236
   Web of Science ®Google Scholar
• Casida J. E., Augustinsson KB. Reaction of plasma albumin with 1-naphthyl-N-methylcarbamate (the insecticide, Sevin) and certain other esters. Biochem. Biophys. Acta 1959; 36: 411
   PubMed Web of Science ®Google Scholar
• Casida J. E., Augustinsson K. B., Jonsson G. Stability toxicity and reaction mechanism with esterases of certain carbamate insecticides,/. Econ. Entom. 1960; 53: 205
   Web of Science ®Google Scholar
• Mark LC., Kayden H. J., Steele J. M., Cooper J. R., Berlin I., Rovenstine E. A., Brodie BB. The physiological disposition and cardiac effects of procaine amide. J. Pharm. Exp. Ther. 1951; 102: 5
   PubMedGoogle Scholar
• Crick J., Jackson H. A tracer study of the metabolism of p-iodophenyl methane. The selective localisation of radioactive material (rats). Brit. J. Pharmacol. Chemother. 1952; 7: 142
   PubMed Web of Science ®Google Scholar
• Dutton GJ. Glucuronic Acid, Free and Combined. Academic Press, London 1966
   Google Scholar
• Robbins P. W., Lipmann F. Isolation and identification of active sulphate. J. Biol. Chem. 1957; 224: 837
   Google Scholar
• Nose Y., Lipmann F. Separation of Steroid sulphokinases. J. Biol. Chem. 1958; 233: 1348
   PubMed Web of Science ®Google Scholar
• Gregory J. D., Lipmann F. The transfer of sulphate among phenolic compounds with 3′,5′-diphosphoadeno-sine as coenzyme. J. Biol. Chem. 1957; 229: 1081
   PubMed Web of Science ®Google Scholar
• Roy AB. The enzymic synthesis of aryl sulphamates. Biochem. J. 1960; 74: 49
   PubMed Web of Science ®Google Scholar
• Knaak J. B., Tallant M. J., Bartley W. J., Sullivan LJ. The metabolism of carbaryl in the rat, guinea pig, and man. J. Agr. Food Chem. 1965; 13: 537
   Web of Science ®Google Scholar
• Holder G. M., Ryan AJ. Metabolism of propham (isopropyl-N-phenylcarbamate) in the rat. Nature, (London) 1968; 220: 77
   PubMed Web of Science ®Google Scholar
• Matsumara J., Ward CJ. Degradation of insecticides by human and rat liver. Metabolic fate of carbaryl malathion and parathion. Arch. Environ. Health 1966; 13: 257
   PubMedGoogle Scholar
• Hassan A., Zayed S. M. A. D., Abdel-Hamid FM. Metabolism of carbamate drugs I. Metabolism of 1-naphthyl-N-methylcarbamate (Sevin) in the rat. Biochem. Pharmacol 1966; 15: 2045
   PubMed Web of Science ®Google Scholar
• Knaak J. B., Sullivan LJ. Metabolism of carbaryl in the dog. J. Agr. Food Chem. 1967; 15: 1125
   PubMed Web of Science ®Google Scholar
• Knaak J. B., Sullivan L. J., Wills JH. Metabolism of carbaryl in man. Toxic Appl. Pharmacol 1967; 10: 390
   Web of Science ®Google Scholar
• Knaak J. B., Tallant M. J., Kozbett S. J., Sullivan LJ. The metabolism of carbaryl in man, monkey, pig and sheep. J. Agr. Food Chem. 1968; 16: 465
   Web of Science ®Google Scholar
• Dorough HW. Carbaryl-14C metabolism in a lactating cow. J. Agr. Food Chem. 1967; 15: 261
   Web of Science ®Google Scholar
• Baron R. J., Sphon J. A., Chen J. T., Lustig E., Doherty J. D., Hansen E. A., Kolbye SM. Confirmatory isolation and identification of a metabolite of carbaryl in urine and milk. J. Agr. Food Chem. 1969; 17: 883
   Web of Science ®Google Scholar
• Paulson GD., Zaylskie R. G., Zehr M. V., Portnoy C. E., Feil VJ. Metabolites of carbaryl (1-naphthyl methyl carbamate) in chicken urine. J. Agr. Food Chem. 1970; 18: 110
   PubMed Web of Science ®Google Scholar
• Whitehurst W. E., Bishop E. T., Critchfield J. E., Gyrisco GG., Huddleston E. W., Arnold H., Lisk D. J. The metabolism of Sevin in dairy cows. J. Agr. Food Chem. 1963; 11: 167
   Web of Science ®Google Scholar
• Bend J. R., Holder G. M., Protos E., Ryan AJ. Metabolism of carbaryl in the cattle tickBoophilus microplus (Canestrini). Aust. J. Biol Sci. 1970; 23: 361
   Google Scholar
• Bend J. R., Holder G. M., Protos E., Ryan AJ. Water soluble metabolites of carbaryl (1-naphthyl-N-methylcarbamate) in mouse liver preparation and the rat. Aust. J. Biol. Sci. 1971, in press
   PubMedGoogle Scholar
• Boyland E., Ramsay G. S., Sims P. Metabolism of polycyclic compounds. 18. The secretion of metabolites of naphthalene, l:2-dihydronaphthalene and l:2-epoxy-l:2:3:4-tetrahydronaphthalene in rat bile. Biochem. J. 1961; 78: 376
   PubMed Web of Science ®Google Scholar
• Strother A. Comparative metabolism of selected N-methylcarbamates by human and rat liver fractions. Biochem. Pharmacol 1970; 19: 2525
   PubMed Web of Science ®Google Scholar
• Corduan C. Herbicides and their effect on plants. Mitt. Deutsch. Pharm. Ges. 1970; 40: 29
   PubMedGoogle Scholar
• Bend J. R., Holder G. M., Ryan AJ. Further studies on the metabolism of propham (wopropyl-N-phenylcarbamate) in the rat. Food Cosmet. Toxi. 1971, in press
   PubMedGoogle Scholar
• Elson L. A., Goulden F., Warren FL. Metabolism of aromatic amines in relation to carcinogenesia. Brit. J. Cancer 1958; 12: 108
   PubMed Web of Science ®Google Scholar
• Grunow WB., Ohme Chr., Budczies B. Uben den Stoffwechsel von carbamat-Herbiciden in der Ratte. 2. Mitteilung. Stoffwechsel von Chlorpropham und Barban. Food Cosmet Toxic 1970; 8: 277
   PubMedGoogle Scholar
• Kearney P. G., Kaufmann DD. Enzyme from soil bacterium hydrolyses phenylcarbamate herbicides. Science (N. Y.) 1965; 147: 740
   PubMed Web of Science ®Google Scholar
• Metcalf R. L., Fukuto T. R., Wilkinson C, Falong M. H., Abd El-Azey S., Metcalf ER. Mode of action of carbamate synergists. J. Agr. Food Chem. 1966; 14: 555
   Web of Science ®Google Scholar
• Dorough HW. Metabolism of insecticidal methylcarbamates in animals. J. Food Agr. Chem. 1970; 18: 1015
   PubMed Web of Science ®Google Scholar
• Brodie BB. private communication to Professor T. R. Watson. University of Sydney
   Google Scholar