Anaerobic transformation of compounds of technical toxaphene. I. Regiospecific reaction of chlorobornanes with geminal chlorine atoms

Environmental Toxicology and Chemistry

Volumn 22, Issue 11, 2003, Pages 2614-2621

  Ruppe, Steffen ^a   Neumann, Anke ^a   Vetter, Walter ^a,b  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

Anaerobic transformation; Chlorobornane dechlorination; Dehalospirillum multivorans; Toxaphene

Indexed keywords

ANAEROBIC DIGESTION; BACTERIOLOGY; CHLORINE COMPOUNDS; SEDIMENTS; SEWAGE SLUDGE; SOILS;

PRIMARY CARBON;

ENVIRONMENTAL ENGINEERING;

2,2,5,5,8,9,9,10,10 NONACHLOROBORNANE; 2,3,5,6,8,8,9,10 OCTACHLOROBORNANE; 2,3,5,6,8,8,9,10,10 NONACHLOROBORNANE; 2,3,5,6,8,9,10,10 OCTACHLOROBORNANE; 2,3,5,9,9,10,10 HEPTACHLOROBORNANE; BORNANE DERIVATIVE; CAMPHECLOR; CHLORINE; CHLOROBORNANE DERIVATIVE; HYDROGEN; OCTACHLOROBORNANE; UNCLASSIFIED DRUG;

DECHLORINATION; TRANSFORMATION;

ANAEROBIC BACTERIUM; ANAEROBIC METABOLISM; ARTICLE; BIOTRANSFORMATION; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DECHLORINATION; NONHUMAN; PRIORITY JOURNAL; SLUDGE; SOIL POLLUTION; SUBSTITUTION REACTION;

BIOTRANSFORMATION; BORNANES; CHLORINE; EPSILONPROTEOBACTERIA; INSECTICIDES; OXYGEN; TOXAPHENE;

BACTERIA (MICROORGANISMS); SULFUROSPIRILLUM; SULFUROSPIRILLUM MULTIVORANS;

EID: 0141557622     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/02-605     Document Type: Article

References (39)

1. Saleh MA. 1991. Toxaphene: Chemistry, biochemistry, toxicity and environmental fate. Rev Environ Contam Toxicol 118:1-95.
2. Vetter W, Oehme M. 2000. Toxaphene. analysis and environmental fate of congeners. In Paasivirta J, ed, The Handbook of Environmental Chemistry, Vol 3, Part K-New Types of Persistent Halogenated Compounds. Springer Verlag, Heidelberg, Germany, pp 237-287.
3. Khalifa S, Mon TR, Engel JL, Casida JE. 1974. Isolation of 2,2,5-endo, 6-exo, 8,9,10-heptachlorobornane and an octachloro toxicant from technical toxaphene. J Agric Food Chem 22:653-657.
4. Turner WV, Khalifa S, Casida JE. 1975. Toxaphene toxicant A: Mixture of 2,2,5-endo, 6-exo, 8,8,9,10-octachlorobornane and 2,2,5-endo, 6-exo, 8,9,9,10-octachlorobornane. J Agric Food Chem 23:991-994.
5. Stern GA, Muir DCG, Ford CA, Grift NP, Dewailly E, Bidleman TF, Walla MD. 1992. Isolation and identification of two major recalcitrant toxaphene congeners in aquatic biota. Environ Sci Technol 26:1838-1840.
6. Vetter W, Luckas B, Oehme M. 1992. Isolation and purification of the two main toxaphene congeners in marine organisms. Chemosphere 25:1643-1652.
7. Williams RR, Bidleman TF. 1978. Toxaphene transformation in estuarine sediments. J Agric Food Chem 26:280-282.
8. Harder HW, Carter TV, Bidleman TF. 1983. Acute effects of toxaphene and its sediment-transformed products on estuarine fish. Can J Fish Aquat Sci 40:2119-2125.
9. Miskimmin BM, Muir DCG, Schindler DW, Stern GA, Grift NP. 1995. Chlorobornanes in sediments and fish after toxaphene treatment of lakes. Environ Sci Technol 29:2490-2495.
10. Stern GA, Loewen MD, Miskimmin BM, Muir DCG, Westmore JB. 1996. Characterization of two major toxaphene components in treated lake sediment. Environ Sci Technol 30:2251-2258.
11. Buser HR, Haglund P, Müller MD, Poiger T, Rappe C. 2000. Rapid anaerobic transformation of toxaphene in sewage sludge. Chemosphere 40:1213-1220.
12. Vetter W, Maruya KA. 2000. Congener and enantioselective analysis of toxaphene in sediment and food web of a contaminated estuarine wetland. Environ Sci Technol 34:1627-1635.
13. Fingerling G, Hertkorn N, Parlar H. 1996. Formation and spectroscopic investigation of two hexachlorobornanes from six environmentally relevant toxaphene components by reductive dechlorination in soil under anaerobic conditions. Environ Sci Technol 30:2984-2992.
14. Vetter W, Bartha R, Stern G, Tomy G. 1999. Enantioselective determination of two persistent chlorobornane congeners in sediment from a toxaphene-treated Yukon lake. Environ Toxicol Chem 18:2775-2781.
15. Mirsatari SG, McChesney MM, Craigmill AC, Winterlin WL, Seiber JN. 1987. Anaerobic microbial dechlorination: An approach to on-site treatment of toxaphene contaminated soil. J Environ Sci Health B Pestic Food Contam Agric Wastes 22:663-690.
16. Mitra S, Jones WJ. 1997. Anaerobic transformation of toxaphene by an enrichment culture from a historically contaminated site. Proceedings, 97th General Meeting, American Society of Microbiology, Miami Beach, Florida, USA, May 4-8, pp 520-521.
17. Scholz-Muramatsu H, Neumann A, Meßmer M, Moore E, Diekert G. 1995. Isolation and characterization of Dehalospirillum multivorans gen. nov., sp. nov., a tetrachloroethene-utilizing, strictly anaerobic bacterium. Arch Mircobiol 163:48-56.
18. Neumann A, Wohlfarth G, Diekert G. 1996. Purification and characterization of tetrachloroethene reductive dehalogenase from Dehalospirillum multivorans. J Biol Chem 271:16515-16519.
19. Neumann A, Siebert A, Trescher T, Reinhardt S, Wohlfahrt G, Diekert G. 2002. Tetrachloroethene reductive dehalogenase of Dehalospirillum multivorans: Substrate specificity of the native enzyme and the corrinoid cofactor. Arch Microbiol 177:420-426.
20. Vetter V, Scholz E, Luckas B, Maruya KA. 2001. Structure of a persistent heptachlorobornane in toxaphene (B7-1000) agrees with molecular model predictions. J Agric Food Chem 49:759-765.
21. Vetter W, Klobes U, Krock B, Luckas B. 1997. Congener specific separation of compounds of technical toxaphene (CTTs) on a nonpolar CP-Sil 2 phase. Journal of Microcolumn Separations 9:29-36.
22. Vetter W, Klobes U, Hottinger G, Luckas B. 1997. Enantiomeric resolution of persistent compounds of technical toxaphene (CTTs) on t-butyldimethylsilylated β-cyclodextrin phases. Chromatographia 45:255-262.
23. Maruya K, Wakeham SG, Vetter W, Francendese L. 2000. Prominent chlorobornane residues in estuarine sediments contaminated with toxaphene. Environ Toxicol Chem 19:2198-2203.
24. Vetter W, Kirchberg D. 2001. Production of toxaphene enantiomers by enantioselective HPLC after isolation of the compounds from an anaerobically transformed technical mixture. Environ Sci Technol 35:960-965.
25. Vetter W, Luckas B. 1995. Synthesis, isolation and chromatography of perdeuterated α-1,2,3,4,5,6-hexachlorocyclohexane. J High Resolut Chromatogr 18:643-646.
26. Andrews P, Vetter W. 1995. A systematic nomenclature system for toxaphene congeners. Part 1: Chlorinated bornanes. Chemosphere 31:3879-3886.
27. Zhu J, Mulvihill MJ, Norstrom RJ. 1994. Characterization of technical toxaphene using combined high-performance liquid chromatography-gas chromatography-electron capture negative ionization mass spectrometry techniques. J Chromtogr A 669: 103-117.
28. Stern GA, Muir DCG, Billeck B, Lockhart L, Wilkinson P, Miskimmin BM. 1996. Toxaphene congener patterns in lake sediment. Organohalogen Compounds 28:379-384.
29. Parlar H, Angerhöfer D, Coelhan M, Kimmel L. 1995. HRGC and HRGC-ECNI determination of toxaphene residues in fish with a new 22 components standard. Organohalogen Compounds 26: 357-362.
30. Vetter W, Krock B, Luckas B. 1999. GC/MS analysis of 5-exo, 6-exo, 8,10-tetrachlorodihydrocamphene and an unsaturated heptachloro compound isolated from Melipax. Fresenius Environ Bull 8:654-661.
31. Kimmel L, Angerhöfer D, Gill U, Coelhan M, Parlar H. 1998. HRGC/ECD and HRGC/ECNI-SIM-HRMS quantification of toxaphene residues by six environmentally relevant chlorobornanes as standard. Chemosphere 37:549-558.
32. Vetter W, Luckas B. 2000. Enantioselective determination of persistent and partly degradable toxaphene congeners in high trophic level biota. Chemosphere 41:499-506.
33. Karlsson H, Muir D, Strachan W, Bachus S, De Vault D, Whittle DM. 1999. Enantiomer ratios of toxaphene in abiotic an biological samples from Lake Superior. Organohalogen Compounds 41: 597-601.
34. Vetter W, Klobes U, Krock B, Luckas B, Glotz D, Scherer G. 1997. Isolation, structure elucidation and identification of a further major toxaphene compound in environmental samples. Environ Sci Technol 31:3023-3028.
35. Vetter W, Scherer G. 1999. Persistency of toxaphene components in mammals that can be explained by molecular modeling. Environ Sci Technol 33:3458-3461.
36. Arnold WA, Winget P, Cramer CJ. 2002. Reductive dechlorination of 1,1,2,2-terachloroethane. Environ Sci Technol. 36:3536-3541.
37. Vetter W. 1993. Toxaphene. Theoretical aspects of the distribution of chlorinated bornanes including symmetrical aspects. Chemosphere 26:1079-1084.
38. Parlar H, Leupold G, Reil D, Angerhöfer D, Coelhan M. 2001. Structure-environmental transformation relationship model for toxaphene congeners. Fresenius Environ Bull 10:4-17.
39. Nikiforov VA, Karavan VA, Miltsov SA. 2000. Relative retention times of chlorinated monoterpenes. Chemosphere 41:467-472.