Fluorinated organics in the biosphere

Environmental Science and Technology

Volumn 31, Issue 9, 1997, Pages 2445-2454

  Key, Blake D ^a,b   Howell, Robert D ^c   Criddle, Craig S ^a,b  

^a Michigan State University   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c 3M COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCONVERSION; DEHALOGENATION; ENVIRONMENTAL IMPACT;

BIOSPHERE;

FLUORINE COMPOUNDS;

ORGANOFLUORINE DERIVATIVE; VOLATILE AGENT;

BIOCHEMICAL PROCESSES; ENVIRONMENTAL POLLUTANT; ORGANOFLUORINE;

AIR POLLUTANT; AIR POLLUTION; BIOSPHERE; DEFLUORINATION; REVIEW; TROPOSPHERE;

EID: 0031239570     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es961007c     Document Type: Review

References (144)

1. Clarke, D. D. Neurochem. Res. 1991, 16, 1055.
2. Cartwright, D. In Organofluorine chemistry: Principles and commercial applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 237-257.
3. Peters, R. In Carbon-fluorine compounds: Chemistry, biochemistry, and biological activities (A Ciba Foundation Symposium); Associated Scientific Publishers: Amsterdam, 1972; pp 55-76.
4. Schnellmann, R. G.; Randall, O. M. Biochim. Biophys. Acta 1990, 1016, 344.
5. Deocampo, N. D.; Upham, B. L.; Trosko, J. E. Fundam. Appl. Toxicol. (Suppl.) 1996, 30, 1065.
6. Gadelhak, G. G. Ph.D. Dissertation, Michigan State University, 1992.
7. Upham, B. L. Michigan State University, E. Lansing, personal communication, 1996.
8. Smart, B. E. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 57-88.
9. Pauling, L. The nature of the chemical bond, 3rd ed.; Cornell University Press: Ithaca, NY, 1960.
10. Smart, B. E. In Molecular Structure and Energetics; Liebman, J. F., Greenberg, A., Eds.; VCH Publishers: Deerfield, FL, 1986; Vol. 3.
11. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
12. Saunders, B. C. In Carbon-fluorine compounds; chemistry, biochemistry and biological activities (A Ciba Foundation Symposium); Elliott, K., Birch, J., Eds.; Associated Scientific Publishers: Amsterdam, 1972; pp 9-32.
13. Paul, E. A.; Huang, P. M. Handbook of Environmental Chemistry; Springer Verlag: Berlin, 1980.
14. Harper, D. B.; O'Hagen, D. Nat. Prod. Rep. 1994, 11, 123.
15. Suida, J. F.; DeBernardis, J. F. Lloydia 1973, 36, 107.
16. Tamura, T.; Wada, M.; Esaki, N.; Soda, K. J. Bacteriol. 1995, 177, 2265.
17. Isidorov, V. A. Organic Chemistry of the Earth's Atmosphere; Springer-Verlag: Berlin, 1990.
18. Cribble, G. W. Environ. Sci. Technol. 1994, 28, 310.
19. Business Communications Company Inc. RC-193 Performance fluorine chemicals and polymers: Future prospects; Business Communications Company, Inc.: Norwalk, CT, 1995.
20. Carey, J. H.; Fox, M. E.; Schleen, L. P. J. Great Lakes Res. 1988, 14, 338.
21. Allison, M. C. In Industrial Applications of Surfactants (Special Publication 59); Royal Society of Chemistry: London, 1987; pp 333-342.
22. Banitt, E. H.; Coyne, W. E.; McGurran, K. T.; Robertson, J. E. J. Med. Chem. 1974, 17, 116.
23. Elliot, A. J. In Organofluorine chemistry: Principles and commercial applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 145-157.
24. Fielding, H. C. In Organofluorine chemicals and their industrial applications; Banks, R. E., Ed.; Ellis Horwood Ltd.: Chichester, 1979; pp 214-232.
25. Filler, R. In Organofluorine compounds in medicinal chemistry and biomedical applications; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993; pp 1-23.
26. Jaffe, R.; Hites, R. A. Environ. Sci. Technol. 1985, 19, 736.
27. Kissa, E. Fluorinated surfactants: synthesis, properties, and applications; Marcel Dekker, Inc: New York, 1994.
28. Mead, R. J.; Feldwick, M. G.; Bunn, J. T. Wildl. Res. 1991, 18, 27.
29. Moore, G. G. I.; Harrington, J. K. J. Med. Chem. 1975, 18, 386.
30. Moore, G. G. I. J. Org. Chem. 1979, 14, 1708.
31. Moore, G. G. I.; Lappi, L. R.; Bauchhuber, J. E.; Conway, A. C. 106th National Meeting ofthe American Chemical Society; MEDI Abstracts: Chicago, IL, 1970.
32. Rao, N. S.; Baker, B. E. In Organofluorine chemistry: Principles and commercial applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 321-336.
33. Stang, P. J.; White, M. R. Aldrichim. Acta 1983, 16, 15.
34. Trepka, R. D.; Harrington, J. K.; Robertson, J. E.; Waddington, J. T. J. Agric. Food Chem. 1970, 18, 1176.
35. Trepka, R. D.; Harrington, J. K.; McConville, J. W.; McGurran, K. T.; Mendel, A.; Pauly, D. R.; Robertson, J. E.; Waddington, J. T. J. Agric. Food Chem. 1974, 22, 1111.
36. Vander Meer, R. K.; Lofgren, C. S.; Williams, D. F. J. Econ. Entomol. 1985, 78, 1190.
37. Yamanouchi, K.; Heldebrandt, C. Chemtech 1992, 22, 354.
38. Ribbons, D. W.; Cass, A. E. G.; Rossiter, J. T.; Widdowson, D. A.; Williams, S. R.; Baker, P. B.; Martin, R. E. J. Fluor. Chem. 1987, 37, 299.
39. Visscher, P. T.; Culbertson, C. W.; Oremland, R. S. Nature 1994, 369, 729.
40. Goldman, P. J. Biol. Chem. 1965, 240, 3434.
41. Oltmanns, R. H.; Muller, R.; Otto, M. K.; Lingens, F. Appl Environ. Microbiol. 1989, 55, 2499.
42. Spracklin, D. K.; Kharasch, E. D. Chem. Res. Toxicol. 1996, 9, 696.
43. Oremland, R. S.; Matheson, L. J.; Guidetti, J. R.; Schaefer, J. K.; Visscher, P. T. Summary of research results on bacterial degradation of trifluoroacetate (TFA), November, 1994-May, 1995; Open File Report 95-OF 95-0422; USGS: Denver, CO, 1995.
44. Emptage, M. Proceedings of the 1994 AFEAS Workshop on the environmental fate of trifluoroacetic acid; AFEAS Administrative Organization, SPA-AFEAS, Inc.: Miami Beach, FL, 1994.
45. Gorsky, B. H.; Cascorbi, H. F. Anesthesiology 1979, 50, 123.
46. Sonier, D. N.; Duran, N. L.; Smith, G. B. Appl. Environ. Microbiol. 1994, 60, 4567.
47. Lech, J. J. Toxicol. Appl. Pharmacol. 1971, 20, 216.
48. Bothwell, M. L.; Beeton, A. M.; Lech, J. J. J. Fish. Res. Board Can. 1973, 30, 1841.
49. Wackett, L. P.; Sadowsky, M. J.; Newman, L. M.; Hur, H.-G.; Li, S. Lett. Nature 1994, 368, 627.
50. Hagen, D. F.; Belisle, J.; Johnson, J. D.; Venkateswarlu, P. Anal. Biochem. 1981, 118, 336.
51. Schreiber, A.; Hellwig, M.; Dorn, E.; Reineke, W.; Knackmuss, H. Appl. Environ. Microbiol. 1980, 39, 58.
52. Ghantous, H.; Parnerud, I.; Danielsson, B. R. G.; Dencker, L. Acta Pharmacol. Toxicol. 1986, 59, 370.
53. Meyer, J. J. M.; O'Hagan, D. Phytochemistry 1992, 31, 2699.
54. Horiuchi, N. Seikagaku 1962, 34, 92.
55. Leung, L. S.; Frey, P. A. Biochem. Biophys. Res. Commun. 1978, 81, 274.
56. Tewfik, M. S.; Hamdi, Y. A. Soil Biol. Biochem. 1975, 7, 79.
57. Blake, D. A.; Cascorbi, H. F.; Rozman, R. S.; Meyer, F. J. Toxicol. Appl. Pharmacol. 1969, 15, 83.
58. W. M. O. Global Ozone Research and Monitoring Project; Scientific Assessment of Stratospheric Ozone: 1989, Vol. I & II; Report 20; World Meteorological Organization: Geneva, Switzerland, 1989.
59. Molina, M. J.; Rowland, F. S. Nature 1974, 249, 810.
60. Rowland, F. S.; Molina, M. J. Rev. Geophys. Space Phys. 1975, 13, 1.
61. Tromp, T. K.; Ko, M. K. W.; Rodriguez, J. M.; Sze, N. D. Nature 1995, 376, 327.
62. Wallington, T. J.; Hurley, M. D.; Ball, J. C.; Kaiser, E. W. Environ. Sci. Technol. 1992, 26, 1318.
63. Belisle, J. Science 1981, 212, 1509.
64. Gilliland, F. D.; Mandel, J. S. Am. J. Ind. Med. 1996, 29, 560.
65. Guy, W. S.; Taves, D. R.; Brey, W. S. In Biochemistry Involving Carbon-Fluorine Bonds; Filler, R., Ed.; American Chemical Society: Washingtion, DC, 1976; Vol. 28.
66. Fisher, D. A.; Hales, C. H.; Wang, W. C.; Ko, M. K. W.; Sze, N. D. Nature 1990, 344, 513.
67. Semprini, L.; Hopkins, G. D.; Roberts, P. V.; McCarty, P. L. EOS, Trans. Am. Geophys. Union 1990, 71, 1324.
68. Denovan, B. A.; Strand, S. E. Chemosphere 1992, 24, 935.
69. Lovely, D. R.; Woodward, J. C. EOS, Trans. Am. Geophys. Union 1990, 71, 1236.
70. Lesage, S.; Brown, S.; Hosler, K. R. Chemosphere 1992, 24, 1225.
71. Hur, H.-G.; Sadowsky, M. J.; Wackett, L. P. Appl. Environ. Microbiol. 1994, 60, 4148.
72. Lovely, D. R.; Woodward, J. C. Environ. Sci. Technol. 1992, 26, 925.
73. Krone, U. E.; Thauer, R. K. FEMS Microbiol. Lett. 1992, 90, 201.
74. Wallington, T. J.; Schneider, W. F.; Womsnop, D. R.; Nielsen, O. J.; Sehested, J.; Debruyn, W. J.; Shorter, J. A. Environ. Sci. Technol. 1994, 28, 320.
75. AFEAS. Production, sales, and atmospheric release of fluorocarbons through 1994; Alternative Fluorocarbons Environmental Acceptability Study (AFEAS): 1996.
76. Franklin, J. Chemosphere 1993, 27, 1565.
77. Tromp, T. K.; Rodriguez, J. M.; Ko, M. K. W.; Heisey, C. W.; Sze, N. D. Proceedings of the 1994 AFEAS Workshop on the environmental fate of trifluoroacetic acid; AFEAS Administrative Organization, SPA-AFEAS, Inc.: Miami Beach, FL, 1994.
78. Schwarzbach, S. E. Nature 1995, 376, 297.
79. Oremland, R. S.; Lonergan, D. J.; Culbertson, C. W.; Lovely, D. R. Appl. Environ. Microbiol. 1996, 62, 1818.
80. Olson, M. J.; Reidy, C. A.; Johnson, J. T.; Pederson, T. C. Drug Metab. Dispos. 1990, 18, 992.
81. DeFlaun, M. F.; Ensley, B. D.; Steffan, R. J. Biotechnology 1992, 10, 1576.
82. Chang, W. K.; Criddle, C. S. Biodegradation 1995, 6, 1.
83. Ma, T. G.; Ling, Y. H.; McClure, G. D.; Tseng, M. T. J. Toxicol. Environ. Health 1990, 31, 147.
84. Blake, D. A.; Rozman, R. S.; Cascorbi, H. F.; Krantz, J. C. Biochem. Pharmacol. 1967, 16, 1237.
85. Van Dyke, R. A. Environ. Health Perspect. 1977, 21, 121.
86. Mukai, S.; Mono, M.; Fuujii, K.; Hanaki, C. Anesthesiology 1977, 47, 248.
87. Sutton, T. S.; Kolbin, D. D.; Gruenke, L. D. Anesth. Analg. 1991, 73, 180.
88. Mazze, R.; Hitt, B. Drug Metab. Dispos. 1978, 6, 680.
89. Engesser, K. H.; Cain, R. B.; Knackmuss, H. Arch. Microbiol. 1988, 149, 188.
90. Engesser, K. H.; Cain, R. B.; Knackmuss, H. Arch. Microbiol. 1988, 149, 198.
91. Engesser, K. H.; Rubio, M. A.; Knackmuss, H. Appl. Microbiol. Biotechnol. 1990, 32, 600.
92. NASS/ERS. Agricultural Chemical Usage - 1995 Field Crop Summaries; Report Ag Ch 1 (96); USDA: Washington, DC, 1996.
93. Golab, T.; Occolowitz, J. L. Biomed. Mass Spectrom. 1979, 6, 1.
94. Erkog, F. U.; Menzer, R. E. J. Agric. Food. Chem. 1985, 33, 1061.
95. Probst, G. W.; Golab, T.; Herberg, R. J.; Holzer, F. J.; Parka, S. J.; van der Schans, C.; Tepe, J. B. J. Agric. Food. Chem. 1966, 15, 592.
96. Williams, P. P.; Feil, V. J. J. Agric. Food. Chem. 1971, 19, 1198.
97. Worthington, P. A. In Synthesis and Chemistry of Agrochemicals; Baker, D. R., Fenyes, J. G., Moberg, W. K., Cross, B., Eds.; ACS Symposium Series 355; American Chemical Society: Washington, DC, 1987; pp 302-315.
98. Great Lakes Fishery Commission, Ann Arbor, MI, personal communication, 1996.
99. Carey, J. H.; Fox, M. E. J. Great Lakes Res. 1981, 7, 234.
100. Hewitt, L. M.; Munkittrick, K. R.; Scott, I. M.; Carey, J. H.; Solomon, K. R.; Servos, M. R. Environ. Toxicol. Chem. 1996, 15, 894.
101. Du Boisson, R. A. In Organofluorine chemistry: Principles and commercial applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; pp 579-593.
102. Seuferer, S. L.; Braymer, H. D.; Dunn, J. J. Pestic. Biochem. Physiol. 1979, 10, 174.
103. Wilson, J. E. H.; Cunningham, P. A.; Evans, D. W.; Costlow, J. D. In Environmental toxicology and risk assessment; Hughes, J. S., Biddinger, G. R., Mones, E., Eds.; American Society for Testing and Materials: Philadelphia, 1995; Vol. 3.
104. Engesser, K. H.; Auling, G.; Busse, J.; Knackmuss, H. Arch. Microbiol. 1990, 153, 193.
105. Goldman, P. Degradation of synthetic organic molecules in the biosphere; National Academy of Sciences: Washington, DC, 1971; pp 147-165.
106. Schlomann, M.; Fischer, P.; Schmidt, E.; Knackmuss, H. J. Bacteriol. 1990, 172, 5119.
107. Schennen, U.; Braun, K.; Knackmuss, H. J. Bacteriol. 1985, 161, 321.
108. Guo, W.; Brown, T. A.; Fung, B. M. J. Phys. Chem. 1991, 95, 1829.
109. Grossman, M. R.; Mispagel, M. E.; Bowen, J. M. J. Agric. Food. Chem. 1992, 40, 2505.
110. Manning, R. O.; Bruckner, J. V.; Mispagel, M. E.; Bowen, J. M. Drug Metab. Dispos. 1991, 19, 205.
111. Arrendale, R. F.; Stewart, J. T.; Manning, R.; Vitayavirasuk, B. J. Agric. Food. Chem. 1989, 37, 1130.
112. Abe, T.; Nagase, S. In Preparation, properties, and industrial applications of organofluorine compounds; Banks, R. E., Ed.; John Wiley & Sons: New York, 1982; pp 19-44.
113. Key, B. D. Ph.D. Dissertation, Michigan State University, 1996.
114. Ophaug, R. H.; Singer, L. Proc. Soc. Exp. Biol. Med. 1980, 163, 19.
115. Atzert, S. P. A review of sodium monofluoroacetate (compound 1080) its properties, toxicology, and use in predator and rodent control; Special Science Report on Wildlife 146; U.S. Fish and Wildlife Service: Washington, DC, 1971.
116. Goldman, P.; Milne, G. W. A. J. Biol. Chem. 1966, 241, 5557.
117. Goldman, P.; Milne, G. W. A.; Keister, D. B. J. Biol. Chem. 1968, 243, 428.
118. Kelly, M. Nature 1965, 208, 809.
119. Meyer, J. J. M.; Grobbelaar, N.; Steyn, P. L. Appl. Environ. Microbiol. 1990, 56, 2152.
120. Tonomura, K.; Futai, F.; Tanabe, O.; Yamaoka, T. Agric. Biol. Chem. 1965, 29, 124.
121. Walker, J. R. L.; Lien, B. C. Soil Biol. Biochem. 1981, 13, 231.
122. Gregg, K.; Cooper, C. L.; Schafer, D. J.; Sharpe, H.; Beard, C. E.; Allen, G.; Xu, J. Bio/Technology 1994, 12, 1361.
123. Trosko, J. E.; Jone, C.; Chang, C. C. Mol. Toxicol. 1987, 1, 83.
124. Holder, J. W.; Elmore, E.; Barrett, J. C. Cancer Res. 1993, 53, 3475.
125. Yamasaki, H.; Naus, C. C. G. Carcinogenesis 1996, 17, 1199.
126. Trosko, J. E.; Chang, C.; Netzloff, M. Teratog. Carcinog. Mutagen. 1982, 2, 31.
127. Trosko, J. E.; Chang, C.; Madhukar, B. V. Risk Anal. 1994, 14, 303.
128. Ye, Y.; Bombick, D.; Hirst, K.; Zhang, G.; Chang, C.; Trosko, J. E.; Akera, T. Fundam. Appl. Toxicol. 1990, 14, 817.
129. Bergoffen, J.; Scherer, S. S.; Wnag, S.; Oronzi Scott, M.; Bone, L. J.; Paul, D. L.; Chen, K.; Lensch, M. W.; Chance, P. F.; Fischbeck, K. H. Science 1993, 262, 2039.
130. Chauhan, S.; Tiedje, J. M.; Criddle, C. S. Manuscript in preparation.
131. Edney, E. O.; Gay, B. W.; Driscoll, D. J. J. Atmos. Chem. 1991, 12, 105.
132. Kotamarthi, V. R. EOS, Trans. Am. Geophys. Union 1994, 75, 137.
133. Wallington, T. J.; Hurley, M. D.; Fracheboud, J. M.; Orlando, J. J.; Tyndall, G. S.; Sehested, J.; Mogelberg, T. E.; Nielson, O. J. J. Phys. Chem. 1996, 100, 18116.
134. Frank, H.; Klein, A.; Renschen, D. Nature 1996, 382, 34.
135. Driscoll, C. T. Proceedings of the 1994 AFEAS Workshop on the environmental fate of trifluoroacetic acid; AFEAS Administrative Organization, SPA-AFEAS, Inc.: Miami Beach, FL, 1994.
136. Calamari, D. Proceedings of the 1994 AFEAS Workshop on the environmental fate of trifluoroacetic acid; AFEAS Administrative Organization, SPA-AFEAS, Inc.: Miami Beach, FL, 1994.
137. Thompson, R. S. Proceedings of the 1994 AFEAS Workshop on the environmental fate of trifluoroacetic acid; AFEAS Administrative Organization, SPA-AFEAS, Inc.: Miami Beach, FL, 1994.
138. Bott, T. L.; Standley, L. J. Proceedings of the 1994 AFEAS Workshop on the environmental fate of trifluoroacetic acid; AFEAS Administrative Organization, SPA-AFEAS, Inc.: Miami Beach, FL, 1994.
139. Blake, D. A.; DiBlasi, M. C.; Gorden, G. B. Fundam. Appl. Toxicol. 1981, 1, 415.
140. Stock, J. G.; Strunin, L. Anesthesiology 1985, 63, 424.
141. Ball, J. C.; Wallington, T. J. J. Air Waste Manage. 1993, 43, 1260.
142. Kenna, J. G.; Martin, J. L.; Satoh, H.; Pohl, L. R. Drug Metab. Dispos. 1990, 18, 788.
143. Taylor, B. F.; Amador, J. A.; Levinson, H. S. FEMS Microbiol. Lett. 1993, 110, 213.
144. Flynn, R. M. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds.; John Wiley & Sons: New York, 1994; Vol. 11, pp 525-534.