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Recent state of lindane metabolism. Part III.

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Residue Reviews

Part of the book series: Residue Reviews ((RECT,volume 94))

Abstract

After publication of part II of our review in 1979 (Residue Reviews 72, 71) knowledge about the mechanisms of the metabolism of lindane and the other hexachlorocyclohexane isomers increased rapidly. The identification of new, till now unknown metabolites recedes and the basic research on mechanism of several degradation steps increased. Nowadays more than 80 lindane metabolites of different chemical structure and relevance are known. Some more than 70 metabolites were found in warm-blooded animals. Fundamental detections of lindane metabolites are listed in Table I in chronological order. Until 1964 only 10, from 1965 to 1970 35, from 1971 to 1975 118, and from 1976 to 1980 238 identifications of metabolites (sometimes of the same metabolites) were reported. Main activities in finding out and identification of unknown metabolites took place in the 70th years.

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References

  • Ahlborg, U., and T. M. Thunberg: Chlorinated phenols: Occurrence, toxicity, metabolism, and environmental impact. CRC Critical Rev. Toxicol. 7, 1 (1980).

    Article  CAS  Google Scholar 

  • Allsup, T., and D. Walsh: Gaschromatographic analysis of chlorophenylmercapturic acid lindane metabolites. J. Chromatog. 236, 421 (1982).

    Article  CAS  Google Scholar 

  • Angerer, J., K. Behling, H.-L. Brassow, and G. Lehnert: Elimination von Hexachlorocyclohexan (HCH) aus dem menschlichen Körper. 22. Jahrestagung der Deutschen Geseelchaft für Arbeitsmedizin e. V., Göttingen (BRD)4.-7.5 (1983 a).

    Google Scholar 

  • Angerer, J., R. Heinrich, and K. Baumann: Metabolism of hexachlorocyclohexane in man. 2nd Int. Congr. Toxicol., Brüssel, July 6–11 (1980). Toxicol. Lett. SI, No. 1, p. 30 (1980).

    Google Scholar 

  • Angerer, J., R. Mass, andR. Heinrich: Occupational exposure to hexachlorocyclohexane. VI. Metabolism of gamma-hexachlorocyclohexane in man. Int. Arch. Occup. Environ. Health 252,59 (1983 b).

    Article  Google Scholar 

  • Bakke, J. E., P. W. Aschbacher, and V. J. Feil: The metabolism of pentachloromethylthio-benzene in germ-free and conventional rats. Xenobiotica 11, 173 (1981).

    Article  PubMed  CAS  Google Scholar 

  • Ballschmiter, K., and Ch. Scholz: Mikrobieller Abbau von chlorierten Aromaten. VI. Bildung von Dichlorphenolen und Dichlorbrenzkatechinen aus Dichlorbenzolen in mikromolarer Lösung durch Pseudomonas sp. Chemosphere 9, 457 (1980).

    Article  CAS  Google Scholar 

  • Ballschmiter, K., and Ch. Scholz: Primärschritte der Umwandlung von Chlorbenzol-Derivaten durch Pseudomonas putida. Angew. Chemie 93, 1026 (1981).

    Article  CAS  Google Scholar 

  • Bayerl, J.: Quantitative Bestimmung von Metaboliten des Fungizids Hexachlorobenzol in Organen von männlichen Ratten. Thesis, Universität München (1980).

    Google Scholar 

  • Bieniok, R.: Verteilung von 14C-Lindan auf Blut und Organe der Ratte und Stoffwechselveränderungen bei Ratte und Maus unter Lindaneinfluß. Thesis, Universität Mainz (1979).

    Google Scholar 

  • Boyd, St. A., and D. R. Shelton: Anaerobic biodegradation of chlorophenols in fresh and acclimated sludge. Applied Environ. Microbiol. 47, 272 (1984).

    CAS  Google Scholar 

  • Bradbury, F. R., and H. Standen: The fate of gamma-benzene hexachloride in normal and resistant houseflies. I. J. Sei. Food Agr. 6, 90 (1955).

    Article  CAS  Google Scholar 

  • Brandt, I., A. Lyden, P. Slanina, and L. Albanus: Hexachlorobenzene (HCB) and some of its sulfur-containing metabolites: tissue retention and excretion routes in mice. In B. Holmstedt, R. Lauwerys, M. Mercier, and M. Roberfroid (eds.): Mechanisms of toxicity and hazard evaluation. Amsterdam, N.Y.: Oxford, Elsevier/North-Holland Biomedical Press (1980).

    Google Scholar 

  • Braun, W. H., J. D. Young, G. E. Blau, and P. J. Gehring: The pharmacokinetics and metabolism of pentachlorophenol in rats. Toxicol. Applied Pharmacol. 41, 395 (1977).

    Article  CAS  Google Scholar 

  • Chadwick, R. W., M. F. Copeland, and C. J. Chadwick: Enhanced pesticide metabolism, a previously unreported effect of dietary fibre in mammals. Food Cosmet. Toxicol. 16, 217 (1978 a).

    Article  PubMed  CAS  Google Scholar 

  • Chadwick, R. W., E. J. Faeder, L. C. King, M. F. Copeland, K. Williams, and L. T. Chuang: Effect of acute and chronic Cd exposure on lindane metabolism. Ecotoxicol. Environ. Safety 2, 301 (1978 c).

    Article  PubMed  CAS  Google Scholar 

  • Chadwick, R. W., M. F. Copeland, and L. Rosenstein: Dode—response effects from kepone exposure during gestation and lactation on the metabolism of lindane by weanling rats. Toxicol. Applied Pharmacol. 48, A93 (1979 a).

    Google Scholar 

  • Chadwick, R. W., M. F. Copeland, and L. Rosenstein:The effect of kepone exposure during gestation and lactation on the metabolism of lindane by weanling rats. Toxicol. Letters 4, 247 (1979 b).

    Article  CAS  Google Scholar 

  • Chadwick, R. W., M. F. Copeland, M. L. Mole, S. Nesnow, and N. Cooke: Comparative effect of pretreatment with phenobarbital, Aroclor 1254, and beta-naphthoflavone on the metabolism of lindane. Pest. Biochem. Physiol. 15, 120(1981).

    Article  CAS  Google Scholar 

  • Chadwick, R. W., M. F. Copeland, R. Froehlich, and N. Cooke: Chlorobenzene—Impaired lindane metabolism and the effects of pretreatment with chlorobenzene, lindane, or chlorobenzene plus lindane. J. Toxicol. Environ. Health 12, 599 (1983).

    Article  PubMed  CAS  Google Scholar 

  • Chadwick, R. W., T. M. Scotti, M. F. Copeland, M. L. Mole, R. Froehlich, N. Cooke, and W. K. McElroy: Antagonism of chlorobenzene-induced hepatotoxicity by lindane. Pest. Biochem. Physiol. 21, 148 (1984).

    Article  CAS  Google Scholar 

  • Chu, J., and E. J. Kirsch: Metabolism of pentachlorophenol by an axenic bacterial culture. Applied Microbiol. 23, 1033 (1972).

    CAS  Google Scholar 

  • Clark, D. E., G. W. Ivie, and B. J. Camp: Effects of dietary hexachlorobenzene on in vivo biotransformation, residue deposition, and elimination of certain xenobiotics by rats. J. Agr. Food Chem. 29, 600 (1981).

    Article  CAS  Google Scholar 

  • Cook, W. L., D. Fieldler, and A. W. Bourquin: Succession of microfungi in estuarine microcosms perturbed by carbaryl, methyl parathion and pentachlorophenol. Bot. Mar. 23, 129 (1980).

    Article  CAS  Google Scholar 

  • Cooper, P.: Hexachlorobenzene metabolism—Mainly in the rat. Food Cosmet. Toxicol. 16, 287 (1978).

    Article  PubMed  CAS  Google Scholar 

  • Cooper, P.: Getting rid of pentachlorophenol. Food Cosmet. Toxicol. 17, 405 (1980).

    Article  Google Scholar 

  • Copeland, M. F., and R. W. Chadwick: Bioisomerization of lindane in rats. J. Environ. Pathol. Toxicol. 2, 737 (1979 a).

    PubMed  CAS  Google Scholar 

  • Copeland, M. F., and R. W. Chadwick: Comparative metabolism of lindane in rats following administration by two oral routes. Toxicol. Applied Pharmacol. 48, A8 (1979 b).

    Google Scholar 

  • Debets, F. M. H., and J. J. T. W. A. Strik: An approach to elucidate the mechanism of hexachlorobenzene-induced hepatic porphyria, as a model for the hepatotoxicity of polyhalogenated aromatic compounds (PHA’s). In J. J. T. W. A. Strik, and J. H. Koeman (eds.): Chemical porphyria in man. Amsterdam, New York: Elsevier, North-Holland Biomedical Press (1979).

    Google Scholar 

  • Debets, F. M. H., J.-H. Reinders, G. Koss, J. Seidel, and A. Strik: Effects of dietary antioxidants on the biotransformation and porphyrinogenic action of hexachlorobenzene in two strains of rats. Chem.-Biol. Interactions 37, 77 (1981 a).

    Article  CAS  Google Scholar 

  • Debets, F. M. H., J.-H. Reinders, G., A. J. M. Debets, and T. G. Lossbroek: Biotransformation and porphyrinogenic action of hexachlorobenzene and its metabolites in a primary liver cell culture. Toxicol. 19, 185 (1981 b).

    Article  CAS  Google Scholar 

  • DFG (Deutsche Forschungsgemeinschaft): Hexachlorcyclohexan-Kontamination— Ursachen, Situation und Bewertung. Kommission zur Prüfung von Rückständen in Lebensmitteln. Mitteilund IX (1982).

    Google Scholar 

  • DFG (Deutsche Forschungsgemeinschaft):Hexachlorcyclohexan als Schadstoff in Lebensmitteln: Materialien aus zwei Kolloquien der Senatskommission zur Prüfung von Rückständen in Lebensmitteln am 28./29. Nov. 1979 und 6. März (1980). Forschungsbericht. Verlag Chemie GmbH, Weinheim (1983).

    Google Scholar 

  • Dutkiewicz, T., and B. Pacholuk: Ocena narazenia na chlorobenzen na podstawie oznac- zania 4-chlorokatecholu w moczu. Med. Pracy XXXI, 289 (1980).

    Google Scholar 

  • Edgerton, T. R., R. F. Moseman, R. E. Linder, and L. H. Wright: Multi-residue method for the determination of chlorinated phenol metabolites in urine. J. Chromatog. 170, 331 (1979).

    Article  CAS  Google Scholar 

  • Engst, R., R. M. Macholz, and M. Kujawa: Metabolismus von Lindan durch Schim-melpilzkulturen. Unkonjugierte Metabolite. Nahrung 18, 737 (1974).

    Article  PubMed  CAS  Google Scholar 

  • Engst, R., W. Fritsche, R. Knoll, M. Kujawa, R. M. Macholz, and G. Straube: Interim results of studies of microbial isomerization of gamma-hexachlorocyclohexane (HCH). Bull. Environ. Contam. Toxicol. 22, 699 (1979 a).

    Article  PubMed  CAS  Google Scholar 

  • Engst, R., R. M. Macholz, and M. Kujawa: The metabolism of lindane in a culture of mould and the general degradation scheme of lindane. Chemosphere 6, 401 (1977 a).

    Article  CAS  Google Scholar 

  • Engst, R., R. M. Macholz, and M. Kujawa:Recent state of lindane metabolism. Residue Reviews 68, 59 (1977 b).

    PubMed  CAS  Google Scholar 

  • Engst, R., R. M. Macholz, and M. Kujawa:Metabolism of gamma-hexachlorcyclohexane (HCH) in vivo. Metabolism of orally administered gamma-2,3,4,5,6-pentachlorocyclohexene. J. Environ. Sci. Health B13, 425 (1978).

    CAS  Google Scholar 

  • Engst, R., R. M. Macholz, and M. Kujawa: Recent state of lindane metabolism. Part II. Residue Reviews 72, 71 (1979 b).

    PubMed  CAS  Google Scholar 

  • Fitzloff, J. F., J. Portig, and K. Stein: Lindane metabolism by human and rat liver microsomes. Xenobiotica 12, 197 (1982).

    Article  PubMed  CAS  Google Scholar 

  • Fukami, J.-I.: Metabolism of several insecticides by glutathion S-transferase. Pharmac. Ther. 10, 473 (1977).

    Article  Google Scholar 

  • Gebefuegi, I., and H. Parlar: Zur Risikoabschätzung von Pentachlorphenol in der Umwelt—Verhalten, Vorkommen und Konsequenzen. GSF-Bericht OE414. Muenchen: Gesellschaft für Strahlen-und Umweltforschung mbH (1978).

    Google Scholar 

  • Gopalaswamy, U. V., and A. S. Aiyar: Metabolism and persistence of lindane in rat tissues. Proc. Symp. Nucl. Techniques in Studies of metabolism. Effect and degradation of pesticides. Dept. Atomic Energy, Govt. India, Bombay, p. 325 (1978).

    Google Scholar 

  • Gopalaswamy, U. V., M. P. Phondke, and A. S. Aiyar: Biotransformation of lindane in mammals and its significance for safety assessment of the pesticide. Proc. Internat. Symp. Use of isotopes for research and control of rectors of animal diseases, host-pathogen relationships and the environmental impact of control procedures. Internat. Atomic Energy Agency, Vienna, 7–11 May (1979).

    Google Scholar 

  • Gopalaswamy, U. V., and A. S. Aiyar: Biotransformation of lindane in the rat. Bull. Environ. Contam. Toxicol. 32, 145 (1984).

    Article  Google Scholar 

  • Grover, and P. Sims: The metabolism of gamma-2,3,4,5,6-pentachlorcyclohex-l-ene and gamma-hexachlorocyclohexane in rats. Biochem. J. 96, 521 (1965).

    PubMed  CAS  Google Scholar 

  • Haider, K., and G. Jagnow: Abbau von 14-C-, 3-H-, und 36-Cl-markiertem gamma- Hexachlorcyclohexan durch anaerobe Bodenmikroorganismen. Arch. Microbiol. 104, 113 (1975).

    Article  PubMed  CAS  Google Scholar 

  • Haider, K., and G. Jagnow:, and K. Rohr: Anaerober Abbau von gamma-Hexachlorcyclohexan durch eine bakterielle Mischflora des Bodens und des Kuhpansens. Landwirtsch. Forsch., Sonderh. 32, Kongreßband (1975).

    Google Scholar 

  • Haque, A.: Metabolism of pesticides in plant tissue cultures to evaluate the quantitative aspects of metabolism. 5th Internat. Congress of Pest. Chem. (IUPAC), Kyoto (Japan), 29. 8.-4. 9. (1982).

    Google Scholar 

  • Hawkins, D. R., L. F. Chasseaud, R. N. Woodhouse, and D. G. Cresswell: The distribution, excretion and biotransformation of p-dichloro-14C-benzene in rat after repeated inhalation, oral and subcutaneous doses. Xenobiotica 10, 81 (1980).

    Article  PubMed  CAS  Google Scholar 

  • Heritage, A. D., and I. C. Macrae: Degradation of hexachlorocyclohexanes and structurally related substances by Clostridium sphevoides. Austr. J. Biol. Sci. 32, 493 (1979).

    CAS  Google Scholar 

  • Heeschen, W., H. Nijhuis, and A. Bluethgen: Untersuchungen zur Bedeutung des Um- und Abbaus von Hexachlorcyclohexan (HCH) im Milchtier und in der Umwelt für die HCH-Kontamination der Milch. Milchwissenschaft 35, 221 (1980).

    CAS  Google Scholar 

  • IARC Monographs on the evaluation of the carcinogenic risk of chemicals to humans: Hexachlorocyclohexane (technical HCH and lindane) 20, 195 (1979).

    Google Scholar 

  • Ingebrigtsen, K., J. U. Skaare, I. Nafstad, and M. Forde: Studies on the biliary excretion and metabolites of hexachlorobenzene in the rat. Xenobiotica 11, 795 (1981).

    Article  PubMed  CAS  Google Scholar 

  • IUPAC (Commission on pesticide chemistry): Environmental chemistry of pen- tachlorophenol. Reports on Pesticides 14. Pure Applied Chem. 53, 1051 (1981).

    Article  Google Scholar 

  • Jakobson, I., and S. Yllner: Metabolism of 14-C-pentachlorophenol in the mouse. Acta Pharmacol. Toxicol. 29, 513 (1971).

    Article  CAS  Google Scholar 

  • Janke, D., and W. Fritsche: Dechlorierung von 4-Chlorphenol nach extradioler Ringspaltung durch Pseudomonas putida. Z. Allgemeine Mikrobiologie 19, 139 (1979).

    Article  CAS  Google Scholar 

  • Jansson, B.: Transformation of some organochlorine compounds in the environment studied by gas chromatography and mass spectrometry. Rept. Nat. Swedish Environ. Prot. Board (1978).

    Google Scholar 

  • Karapally, J. C., J. G. Saha, and Y. W. Lee: Metabolism of lindane-14-C in the rabbit: Ether-soluble urinary metabolites. Abstr. 41, 162nd Nat. Meeting Amer. Chem. Soc., Washington, D.C. (1971).

    Google Scholar 

  • Kaufman, D. D.: Degradation of pentachlorophenol in soil and by soil microorganisms. In K. R. Rao (ed.): Pentachlorophenol. New York: Plenum (1978).

    Google Scholar 

  • Kerklaan, P. R. M., J. J. T. W. A. Strik, and J. H. Koeman: Toxicity of hexachlorobenzene with special reference to hepatic glutathione levels, liver necrosis, hepatic prophyria and metabolites of hexachlorobenzene in female rats fed hexachlorobenzene and treated with phenolbarbital and diethylmaleate. In J. J. T. W. A. Strik, and J. H. Koeman (eds.): Amsterdam, New York, Oxford: Elsevier/North-Holland Biomedical Press (1979).

    Google Scholar 

  • Kimura, R., T. Hayashi, M. Sato, T. Aimoto, and T. Murata: Identification of sulfur-containing metabolites of p-dichlorobenzene and their disposition to rats. J. Pharm. Dyn. 2, 237 (1979).

    CAS  Google Scholar 

  • Kimura, R., M. Kawai, M. Sato, T. Aimoto, and T. Murata: Induction of hepatic microsomal drug-metabolizing enzymes by sulfur-containing metabolites of chlorinated benzenes in rats. Toxicol. Applied Pharmacol. 67, 338 (1983).

    Article  CAS  Google Scholar 

  • Kirsch, E. J., and J. E. Etzel: Microbial decomposition of pentachlorophenol. J. Water Pollut. Control Fed. 45, 359 (1973).

    PubMed  CAS  Google Scholar 

  • Knowlton, M. F.: Transfer of land and pentachlorophenol from aquatic sediments to aquatic vascular plants and crayfish. M. S. Thesis, Univ. Missouri, Columbia, MO (1981).

    Google Scholar 

  • Knowlton, M. F., and J. N. Huckins: Fate of radiolabeled sodium pentachlorophenate in littoral microsomes. Bull. Environ. Contam. Toxicol. 30, 206 (1983).

    Article  PubMed  CAS  Google Scholar 

  • Kobayashi, K.: Metabolism of pentachlorophenol in fishes. In K. R. Rao (ed.): Pen-tachlorophenol. New York: Plenum (1978).

    Google Scholar 

  • Kobayashi, K.: Metabolism of pentachlorophenol in fish. Amer. Chem. Soc. Symp. Ser. 99(Ch. 8), 131 (1979).

    CAS  Google Scholar 

  • Kobayashi, K., S. Kimura, and E. Shimizu: Studies on the metabolism of chlorophenols in fish. IX. Isolation and identification of pentachlorophenyl-beta-glucuronide accumulated in bile of goldfish. Bull. Japan Soc. Sci. Fish 43, 601 (1977).

    CAS  Google Scholar 

  • Koss, G., W. Koransky, and K. Steinbach: Studies on the toxicology of hexachlorobenzene. II. Identification and determination of metabolites. Arch. Toxicol. 35, 107 (1976).

    Article  PubMed  CAS  Google Scholar 

  • Koss, G., S. Seubert, A. Seubert, W. Koransky, and H. Ippen: Studies on the toxicology of hexachlorobenzene. III. Observations in a long-term experiment. Arch. Toxicol. 40, 285 (1978).

    Article  PubMed  CAS  Google Scholar 

  • Koss, G., W. Koransky, and K. Steinbach: Studies on the toxicology of hexachlorobenzene. IV. Sulphur-containing metabolites. Arch. Toxicol. 42, 19 (1979).

    Article  PubMed  CAS  Google Scholar 

  • Kraus, P., and B. Gross: Particle-bound glutathione-S-transferases. Enzyme 24, 205 (1979).

    PubMed  CAS  Google Scholar 

  • Kujawa, M., R. Engst, and R. Macholz: On the metabolism of lindane. In S. H. Zaidi (ed.): Environmental pollution and human health. Proc. Internat. Symp. Indust. Toxicol., Nov. 4–7 ( 1975 ). Ind. Toxicol. Res. Centre, Lucknow, India (1977).

    Google Scholar 

  • Kujawa, M., R. Macholz, and J. Schulze: Bedeutung der Gastrointestinalflora für den Fremdstoff-Metabolismus. Symposium Stand und Perspektiven der gastrointestinalen Mikroökologie, Postdam, GDR, 24.–26. 4 (1984).

    Google Scholar 

  • Kujawa, M., R. Macholz, and J. Schulze: Bedeutung der Gastrointestinalflora für den Fremdstoff-Metabolismus. Symposium Stand und Perspektiven der gastrointestinalen Mikroökologie, Postdam, GDR, 24.–26. 4 (1984).

    Google Scholar 

  • Kurihara, U.: Urinary metabolites from gamma- and beta-BHC in the mouse: Chloro- phenol conjugates. 3rd Internat. Symp. Chem. Toxicol. Aspects of Environ. Qual., Tokyo, Japan, 19–22 Nov. (1973).

    Google Scholar 

  • Kurihara, U., N. Ohisa, M. Nakajima, T. Kakutani, and M. Senda: Relationship between microbial degradability and polarographic half-wave potential of polychlorocyclo- hexenes and BHC isomers. Agr. Biol. Chem. 45, 1229 (1981).

    Article  CAS  Google Scholar 

  • Kurihara, U., K. Tanaka, and M. Nakajima: Pathways of chlorophenylmercaptruic acids formation in biodegradation of lindane. Agr. Biol. Chem. 41, 1317 (1977).

    Article  CAS  Google Scholar 

  • Kurihara, U., K. Tanaka, and M. Nakajima: Anaerobic microsomal metabolism of lindane and related compounds: Reductive dechlorination and dehydrochlorination, its significance in the in vivo metabolism. 5th Internat. Pest. Congress, Zürich, Switzerland, July 24–28 (1978).

    Google Scholar 

  • Kurihara, U., K. Tanaka, and M. Nakajima: Mercaptruic acid formation from lindane in rats. Pest. Biochem. Physiol. 10, 137 (1979 a).

    Article  CAS  Google Scholar 

  • Kurihara, U., K. Tanaka, and M. Nakajima: Anaerobic metabolism of lindane and related compounds by liver microsomes. In H. Geissbuehler (ed.): Advances in pesticide science. Part 3. Biochemistry of pest and mode of action of pesticides. Pesticide degradation. Pesticide residues. Formulation chemistry. Oxford, New York: Pergamon (1979 b).

    Google Scholar 

  • Kurihara, U., T. Suzuki, and M. Nakajima: Deuterium isotope effects on the formation of mercapturic acids from lindane in rats. Biochem. Physiol. 14, 41 (1980 a).

    CAS  Google Scholar 

  • Kurihara, U., Yamakawa, T. Fujita, and M. Nakajima: Anaerobic degradation of tetra-, penta-, and hexachlorocyclohexene isomers by rat liver microsomal P-450. J. Pest. Sci. 5, 93 (1980 b).

    CAS  Google Scholar 

  • Kuwatsuka, S., and M. Igarashi: Degradation of PCP in soils. II. The relationship between the degradation of PCP and the properties of soils, and the identification of the degradation products of PCP. Soil Sci. Plant Nutr. 21, 405 (1975).

    CAS  Google Scholar 

  • Lamoureux, G. L., and D. G. Rusness: Pentachloronitrobenzene metabolism in peanut. 1. Mass spectral characterization of seven glutathione related conjugates produced in vivo or in vitro. J. Agr. Food Chem. 28, 1057 (1980 a).

    Article  CAS  Google Scholar 

  • Lamoureux, G. L., and D. G. Rusness: In vitro metabolism of pentachloronitrobenzene to pentachoromethyl-thiobenzene by onion: Characterization of glutathione S-transferase, cysteine C-S lyase, and S-adenosylmethionine methyl transferase activities. Pest. Biochem. Physiol. 14, 50 (1980 b).

    Article  CAS  Google Scholar 

  • Lech, J. J., A. H. Glickman, and Ch. N. Statham: Studies on the uptake, disposition and metabolism of pentachlorophenol and metabolism of pentachlorophenol and penta- chloroanisole in rainbow trout (Salmo gairdneri). In K. R. Rao (ed.): Pentachlorophenol. New York: Plenum (1978).

    Google Scholar 

  • Leighty, E.G., and A. F. Fentiman: Conjugation of pentachlorophenol in palmitic acid by liver microsomes. Bull. Environ. Contam. Toxicol. 28, 329 (1982).

    Article  PubMed  CAS  Google Scholar 

  • Lievremont, M., J.-F. Le Flohic, and M. Pascaud: Distribution du 14-C-lindane chez le rat apres administration d’une dose unique par voies intraperitoneale et intraveneuse. C. R. Acad. Se. Paris 292(III) (No. 1 ), 45 (1981).

    CAS  Google Scholar 

  • Lingg, R. D., W. H. Kaylor, S. M. Pyle, F. C. Kopfler, C. C. Smith, and G. Wolfe: Comparative metabolism of 1,2,4-trichlorobenzene in the rat and rhesus monkey. Amer. Soc. Pharm. Exper. Therap. 10, 134 (1982).

    CAS  Google Scholar 

  • Lu, P.-Y., R. L. Metealf, and L. K. Cole: The environmental fate of 14-C-pentachloro- phenol in laboratory model ecosystems. In K. R. Rao (ed.): Pentachlorophenol. New York: Plenum (1978).

    Google Scholar 

  • Lyr, H.: Ueber den oxydativen Abbau chlorierter Phenole. Holztechnologie 3, 201 (1962).

    Google Scholar 

  • Macholz, R., R. Engst, R. Knoll, J. Schulze, and M. Kujawa: Comparison of the in vivo metabolism of alpha-, beta-, and gamma-hexachlorocyclohexane. 5th Internat. Congress Pest. Chem. (IUPAC), Kyoto (Japan), 29. 8.-4. 9. (1982).

    Google Scholar 

  • Macholz, R., R. Knoll, M. Kujawa, and R. Engst: Results of studies of microbial isomerization of gamma-hexachlorocyclohexane. Internat. Conf. Xenobiochem., Bratislava (CSSR), June 9–13 (1980).

    Google Scholar 

  • Macholz, R., R. Knoll, H. J. Lewerenz, R. Plass, and J. Schulze: Metabolismus von gamma-Hexachlorcyclohexan (HCH) in keimfreien und konventionalisierten Ratten. Zbl. Pharm. 122, 221 (1983).

    Google Scholar 

  • Macholz, R., R. Knoll, M. Kujawa, H. J. Lewerenz, R. Plass, and G. Straube: Anwendung eines Verfahrens zur gaschromatographischen Trennung und Identifizierung bei Untersuchungen zum Stoffwechsel von Hexachlorcyclohexan-(HCH)-Isomeren. Z. gesamte Hygiene Grenzgebiete 30, 403 (1984 a).

    CAS  Google Scholar 

  • Macholz, R.,, M. Kujawa, J. Schulze, and H. J. Lewerenz: The metabolism of some xenobiotics in germfree and conventionalized rats. 25th Congress European Soc. Toxicol., Budapest, Hungary, June 11–14 (1984 b).

    Google Scholar 

  • Macholz, R.,, M. Kujawa, J. Schulze, and H. J. Lewerenz, and W. Schnaak: The metabolism of some xenobiotics in germ-free and conventionalized rats. Arch. Toxicol., in press (1985).

    Google Scholar 

  • Marinucci, A. C., and R. Bartha: Biodegradation of 1,2,3- and 1,2,4-trichlorobenzene in soil and in liquid enrichment culture. Applied Environ. Microbiol. 38, 811 (1979).

    CAS  Google Scholar 

  • Minard, R. D., S.-Y. Liu, and J.-M. Bollag: Oligomers and quinones from 2,4-dichlorophenol. J. Agr. Food Chem. 29, 250 (1981).

    Article  CAS  Google Scholar 

  • Mottram, D. S., I. E. Psomas, and R. L. S. Patterson: Chlorinated residues in the adispose tissue of pigs treated with gamma-hexachlorocyclohexane. J. Sci. Food Agr. 34, 378 (1983).

    Article  CAS  Google Scholar 

  • Mueller, W. F., I. Scheunert, K. Rozman, W. Kögel, D. Freitag, E. Richter, F. Coulston, and F. Korte: Comparative metabolism of hexachlorobenzene and pentachloronitrobenzene in plants, rats, and rhesus monkeys. Ecotoxicol. Environ. Safety 2, 437 (1978).

    Article  CAS  Google Scholar 

  • Murthy, N. B. K., D. D. Kaufman, and G. F. Fries: Degradation of pentachlorophenol (PCP) in aerobic and anaerobic soil. J. Environ. Sci. Health B14, 1 (1979).

    CAS  Google Scholar 

  • Newland, L. W.: Degradation of gamma-BHC in simulated lake impoundment as affected by aeration. J. Water Pol. Control Fed. 41, R174 (1969).

    CAS  Google Scholar 

  • Ohisa, N., M. Yamaguchi, and N. Kurihara: Lindane degradation by cell-free extracts of Clostridium rectum. Arch. Microbiol. 125, 221 (1980).

    Article  PubMed  CAS  Google Scholar 

  • Ohisa, N., N. Kurihara, and M. Nakajima: ATP synthesis associated with the conversion of hexachlorocyclohexane related compounds. Arch. Microbiol. 131, 330 (1982).

    Article  PubMed  CAS  Google Scholar 

  • Ohisa, N., and M. Y. Yamaguchi: Gamma-BHC degradation accompanied by the growth of Clostridium rectumisolated from paddy field soil. Agr. Biol. Chem. 42, 1819 (1978).

    Article  CAS  Google Scholar 

  • Pan, J., D. P. West, and J. Fitzloff: Unpublished (see Fitzloff et al. 1982 ).

    Google Scholar 

  • Pistor, R.: Untersuchung zur Elimination von Lindan durch Ratten. Thesis, Universität Margburg (1980).

    Google Scholar 

  • Portig, J., P. Kraus, K. Stein, W. Koransky, G. Noack, B. Gross, and S. Sodomann: Glutathione conjugate formation from hexachlorocyclohexane and pentachlorocyclohexane by rat liver in vitro. Xenobiotica 9, 353 (1979).

    Article  PubMed  CAS  Google Scholar 

  • Reinecke, W., and H.-J. Knackmuss: Microbial metabolism of haloaromatics, Isolation and properties of a chlorobenzene-degrading bacterium. Applied Environ. Microbiol. 47, 395 (1984).

    Google Scholar 

  • Reiner, E. A., J. Chu, and E. J. Kirsch: Microbial metabolism of pentachlorophenol. In K. R. Rao (ed.): Pentachlorophenol. New York: Plenum (1978).

    Google Scholar 

  • Renner, J.: Biotransformation of the funigicides hexachlorobenzene and pentachloronitrobenzene. Xenobiotica 21, 435 (1981).

    Article  Google Scholar 

  • Renner, J Formation of pentachlorothioanisole from N-acetyl-S-(pentachlorophenyl)cysteine in blood and liver of rats in vivo. Life Sci. 33, 1427 (1983).

    Article  PubMed  CAS  Google Scholar 

  • Renner, J, E. Richter, and K. P. Schuster: N-acetyl-S-(pentachlorophenyl)cysteine, a new metabolite of hexachlorobenzene. Chemosphere 7, 663 (1978 a).

    Article  CAS  Google Scholar 

  • Renner, J, K. P. Schuster, H. B. Kuhnhen, and H.-D. Stachel: Isolierung von Stoffwechsel-produkten der Pestizide Hexachlorbenzol und Pentachlornitrobenzol aus Harn und Faeces von Ratten und Kaninchen. Chemosphere 7, 943 (1978 b).

    Article  CAS  Google Scholar 

  • Richter, E., G. Renner, J. Bayerl, and M. Wick: Differences in the biotransformation of hexachlorobenzene (HCB) in male and female rats. Chemosphere 10, 779 (1981).

    Article  CAS  Google Scholar 

  • Rizzardini, M., and A. G. Smith: Sex differences in the metabolism of hexachlorobenzene by rats and the development of porphyria in females. Biochem. Pharmacol. 31, 3548 (1982).

    Article  Google Scholar 

  • Rott, B., S. Nitz, and F. Korte: Microbial decomposition of sodium pentachlorophenolate. J. Agr. Food Chem. 27, 306 (1979).

    Article  CAS  Google Scholar 

  • Rozman, K., J. Williams, W. F. Mueller, F. Coulston, and F. Korte: Metabolism and pharmacokinetics of pentachlorobenzene in the rhesus monkey. Bull. Environ. Contam. Toxicol. 22, 190 (1979).

    Article  PubMed  CAS  Google Scholar 

  • Rusness, D. G., andG. L. Lamoureux: Pentachloronitrobenzene metabolism in peanut. 2. Characterization of chloroform-soluble metabolites produced in vivo. J. Agr. Food Chem. 28, 1070 (1980).

    Article  CAS  Google Scholar 

  • Sackmauerova-Veningerova, M., J. Uhnack, A. Szokolay, and A. Kocan: Identification of chlorinated phenols as degradation products of chlorinated pesticides in biological materials. J. Chromatog. 205, 194 (1981).

    Article  CAS  Google Scholar 

  • Saleh, M. A.: Isomerization of lindane by reduced hematin. Bull. Environ. Contam. Toxicol. 25, 833 (1980).

    Article  PubMed  CAS  Google Scholar 

  • Somani, S. M., and A. Khalique: Distribution and metabolism of 2,4-dichlorophenol in rats. J. Toxicol. Environ. Health 9, 889 (1982).

    Article  PubMed  CAS  Google Scholar 

  • Stein, K.: Die biochemische Umwandlung von Hexachlorcyclohexan zu 2,4,6-Trichlor- phenol. Thesis, Fachbereich Humanmedizin, Universität Marburg (1976).

    Google Scholar 

  • Stein, K, and J. Portig: Oxidative transformation of hexachlorocyclohexane in the rat. 17. Spring Meeting, Deutsche Pharmakologische Gesellschaft, Mainz, March 23–26 (1976). Naunyn-Schmiedebergs Arch. Pharmacol. 293, Suppl. R51 (1976).

    Google Scholar 

  • Stein, K, J. Portig, H. Fuhrmann, W. Koransky, and G. Noack: Steric factors in the pharmacokinetics of lindane and alpha-hexachlorocyclohexane in rats. Xenobiotica 10, 65 (1980).

    Article  PubMed  CAS  Google Scholar 

  • Steinwandter, H.: Beiträge zum Lindanmetabolismus in der Ökosphäre. Landw. Forschung 33(II), 208 (1977).

    Google Scholar 

  • Steinwandter, H.: Experiments of lindane metabolism in plants. HI. Formation of beta-HCH. Bull. Environ. Contam. Toxicol. 20, 535 (1978).

    Article  PubMed  CAS  Google Scholar 

  • Steinwandter, H.:, and H. Schlüter: Experiments on lindane metabolism in plants. IV. A kinetic investigation. Bull. Environ. Contam. Toxicol. 20, 174 (1978).

    Article  PubMed  CAS  Google Scholar 

  • Stoeckigt, J., and B. Ries: Catabolism of gamma-hexachlorocyclohexane (lindane) by plants and cell cultures, a comparison, p. 204. In W. Barz, E. Reinhard, and M. H. Zenk (eds.): Plant tissue culture and its bio-technological application. Proc. Life Sei. Berlin, Heidelberg, New York: Springer-Verlag (1977).

    Google Scholar 

  • Strik, J. J. T. W. A., and F. M. H. Debets: Chemical porphyria. In R. D. Kimbrough (ed.): Halogenated biphenyls, terphenyls, naphthalenes, dibenzodioxinds and related products. Amsterdam, New York: Elsevier-North Holland Biomedical Press (1980).

    Google Scholar 

  • Suzuki, T.: Metabolism of pentachlorophenol by a soil microbe. J. Environ. Sci. Health B12, 113 (1977).

    CAS  Google Scholar 

  • Suzuki, T Enzymatic methylation of pentachlorophenol and its related compounds by cell-free extracts of Mycobacteriumsp. isolated from soil. J. Pest. Sci. 3, 441 (1978).

    CAS  Google Scholar 

  • Suzuki, T. Metabolism of pentachlorophenol (PCP) by soil microorganisms. Bull. Nat. Inst. Agr. Sci. C38, 69 (1983 a; in Japanese).

    Google Scholar 

  • Suzuki, T . Methylation and hydroxylation of pentachlorophenol by Mycobacterium sp. isolated from soil. J. Pest. Sci. 8, 419 (1983 b).

    CAS  Google Scholar 

  • Tanaka, K., N. Kurihara, and M. Nakajima: Metabolism of lindane in house flies: Metabolic desaturation, dehydrogenation and dehydrochlorination, and conjugation with glutathione. Pest. Biochem. Physiol. 6, 392 (1976).

    Article  CAS  Google Scholar 

  • Tanaka, K., N. Kurihara, and M. Nakajima: Pathways of chlorophenol formation in oxidative biodegradation of BHC. Agr. Biol. Chem. 41, 723 (1977).

    Article  CAS  Google Scholar 

  • Tanaka, K., N. Kurihara, and M. Nakajima: Oxidative metabolism of lindane and its isomers with microsomes from rat liver and house fly abdomen. Pest. Biochem. Physiol. 10, 96 (1979 a).

    Article  CAS  Google Scholar 

  • Tanaka, K., N. Kurihara, and M. Nakajima: Oxidative metabolism of tetrachlorocyclohexenes, Pentachloro-cyclohexenes and hexachlorocyclohexenes with microsomes from rat liver and house fly abdomen. Pest. Biochem. Physiol. 10, 79 (1979 b).

    Article  CAS  Google Scholar 

  • Tanaka, K, M. Nakajima, and N. Kurihara: The mechanism of resistance to lindane and hexadeuterated lindane in the third Yumenoshima strain of house fly. Pest. Biochem. Physiol. 16, 149 (1981).

    Article  CAS  Google Scholar 

  • Tomizawa, Ch., and H. Kazano: Environmental fate of rice paddy pesticides in a model ecosystem. J. Environ. Sci. Health B14, 121 (1979).

    CAS  Google Scholar 

  • Tsukano, Y., and A. Kobayashi: Formation of gamma-BTC in flooded rice field soils treated with gamma-BHC. Agr. Biol. Chem. 36, 166 (1972).

    Article  CAS  Google Scholar 

  • Van der Linden: Ber. 45, 231 (1912).

    Google Scholar 

  • Vohland, H. W., J. Portig, and K. Stein: Neuropharmacological effects of isomers of hexachlorocyclohexane. Toxicol. Applied Pharmacol. 57, 425 (1981).

    Article  CAS  Google Scholar 

  • Vonk, J. W., and J. K. Quirijns: Anaerobic formation of alpha-hexachlorocyclohexane from gamma-hexachlorocyclohexane in soil and by Escherichia coli. Pest. Biochem. Physiol. 12, 68 (1979).

    Article  CAS  Google Scholar 

  • Waliszewski, S.: The residues of lindane, other isomers of BHC and of HCB in the soil and plants. Materaly XX Sesji Institutu Ochrony Roslin, Poznan, p. 249 (1980).

    Google Scholar 

  • Watanabe, I.: Isolation of pentachlorophenol decomposing bacteria from soil. Soil Sci. Plant. Nutr. 19, 109 (1973).

    CAS  Google Scholar 

  • Weiss, U. M., I. Scheunert, W. Klein, and F. Korte: Fate of pentachlorophenol-14C in soil under controlled conditions. J. Agr. Food Chem. 30, 1191 (1982).

    Article  CAS  Google Scholar 

  • Yang, R. S. H., K. A. Pittman, D. R. Rourke, and V. B. Stein: Pharmacokinetics and metabolism of hexachlorobenzene in the rat and the rhesus monkey. J. Agr. Food Chem. 26, 1076 (1978).

    Article  CAS  Google Scholar 

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Macholz, R.M., Kujawa, M. (1985). Recent state of lindane metabolism. Part III.. In: Gunther, F.A. (eds) Residue Reviews. Residue Reviews, vol 94. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-5104-0_4

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