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Volumn 41, Issue 24, 2007, Pages 8301-8307

Enantioselective microbial transformation of the phenylpyrazole insecticide fipronil in anoxic sediments

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERS; INSECTICIDES; MICROORGANISMS; SLURRIES;

EID: 37249053860     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es071409s     Document Type: Article
Times cited : (55)

References (43)
  • 1
    • 0029851145 scopus 로고    scopus 로고
    • Fipronil insecticide: Novel photochemical desulfinylation with retention of neurotoxicity
    • Hainzl, D.; Casida, J. D. Fipronil insecticide: Novel photochemical desulfinylation with retention of neurotoxicity. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12764-12767.
    • (1996) Proc. Natl. Acad. Sci. U.S.A , vol.93 , pp. 12764-12767
    • Hainzl, D.1    Casida, J.D.2
  • 2
    • 0032411536 scopus 로고    scopus 로고
    • Mechanisms for selective toxicity of fipronil insecticide and its sulfone metabolite and defulfinyl photoproduct
    • Hainzl, D.; Cole, L. M.; Casida, J. E. Mechanisms for selective toxicity of fipronil insecticide and its sulfone metabolite and defulfinyl photoproduct. Chem. Res. Toxicol. 1998, 11, 1529-1535.
    • (1998) Chem. Res. Toxicol , vol.11 , pp. 1529-1535
    • Hainzl, D.1    Cole, L.M.2    Casida, J.E.3
  • 3
    • 37249019425 scopus 로고    scopus 로고
    • New pesticide fact sheet: EPA737-F-96-005. Office of Prevention, Pesticides and Toxic Substances; U.S. Environmental Protection Agency: Washington, DC, 1996.
    • New pesticide fact sheet: EPA737-F-96-005. Office of Prevention, Pesticides and Toxic Substances; U.S. Environmental Protection Agency: Washington, DC, 1996.
  • 4
    • 0030845271 scopus 로고    scopus 로고
    • Effects of very low doses of fipronil on grasshoppers and non-target insects following field trials for grasshopper control
    • Balanca, G.; de Visscher, M. N. Effects of very low doses of fipronil on grasshoppers and non-target insects following field trials for grasshopper control. Crop Prot. 1997, 16, 553-564.
    • (1997) Crop Prot , vol.16 , pp. 553-564
    • Balanca, G.1    de Visscher, M.N.2
  • 6
    • 0346098053 scopus 로고    scopus 로고
    • Fipronil effects on estuarine copepod (Amphiascus tenuiremis) development, fertility, and reproduction: A rapid life-cycle assay in 96-well Microplate format
    • Chandler, G. T.; Cary, T. L.; Volz, D. C.; Walse, S. S.; Ferry, J. L.; Klosterhaus, S. L. Fipronil effects on estuarine copepod (Amphiascus tenuiremis) development, fertility, and reproduction: a rapid life-cycle assay in 96-well Microplate format. Environ. Toxicol. Chem. 2004, 23, 117-124.
    • (2004) Environ. Toxicol. Chem , vol.23 , pp. 117-124
    • Chandler, G.T.1    Cary, T.L.2    Volz, D.C.3    Walse, S.S.4    Ferry, J.L.5    Klosterhaus, S.L.6
  • 7
    • 9644295831 scopus 로고    scopus 로고
    • Population consequences of fipronil and degradates to copepods at field concentrations: An integration of life cycle testing with Leslie matrix population modeling
    • Chandler, G. T.; Cary, T. L.; Bejarano, A. C.; Pender, J.; Ferry, J. L. Population consequences of fipronil and degradates to copepods at field concentrations: an integration of life cycle testing with Leslie matrix population modeling. Environ. Sci. Technol. 2004, 38, 6407-6414.
    • (2004) Environ. Sci. Technol , vol.38 , pp. 6407-6414
    • Chandler, G.T.1    Cary, T.L.2    Bejarano, A.C.3    Pender, J.4    Ferry, J.L.5
  • 8
    • 0347635257 scopus 로고    scopus 로고
    • Phenylpyrazole insecticide fipronil induces male infertility in the estuarine meiobenthic crustacean Amphiascus tenuiremis
    • Cary, T. L.; Chandler, G. T.; Volz, D. C.; Walse, S. S.; Ferry, J. L. Phenylpyrazole insecticide fipronil induces male infertility in the estuarine meiobenthic crustacean Amphiascus tenuiremis. Environ. Sci. Technol. 2004, 38, 522-528.
    • (2004) Environ. Sci. Technol , vol.38 , pp. 522-528
    • Cary, T.L.1    Chandler, G.T.2    Volz, D.C.3    Walse, S.S.4    Ferry, J.L.5
  • 9
    • 0001432106 scopus 로고    scopus 로고
    • Factors influencing the adsorption of fipronil on soils
    • Bobe, A.; Coste, C. M.; Cooper, J. F. Factors influencing the adsorption of fipronil on soils. J. Agric. Food. Chem. 1997, 45, 4861-4865.
    • (1997) J. Agric. Food. Chem , vol.45 , pp. 4861-4865
    • Bobe, A.1    Coste, C.M.2    Cooper, J.F.3
  • 10
    • 0029082012 scopus 로고
    • Actions of the insecticide fipronil on dieldrin sensitive and resistant GABA receptors of Drosophila melanogaster
    • Hosie, A. M.; Baylis, H. A.; Buckingham, S. D.; Sattelle, D. B. Actions of the insecticide fipronil on dieldrin sensitive and resistant GABA receptors of Drosophila melanogaster. Br. J. Pharmacol. 1995, 115, 909-912.
    • (1995) Br. J. Pharmacol , vol.115 , pp. 909-912
    • Hosie, A.M.1    Baylis, H.A.2    Buckingham, S.D.3    Sattelle, D.B.4
  • 11
    • 29344472907 scopus 로고
    • Action of phenylpyrazole insecticides at the GABA-gated chloride channel
    • Cole, L. M.; Nicholson, R. A.; Casida, J. E. Action of phenylpyrazole insecticides at the GABA-gated chloride channel. Pestic. Biochem. Physiol. 1993, 46, 47-54.
    • (1993) Pestic. Biochem. Physiol , vol.46 , pp. 47-54
    • Cole, L.M.1    Nicholson, R.A.2    Casida, J.E.3
  • 13
    • 33746693727 scopus 로고    scopus 로고
    • Phototransformation of the insecticide fipronil: Identification of novel photoproducts and evidence for an alternative pathway of photodegradation
    • Raveton, M.; Aajoud, A.; Willison, J. C.; Aouadi, H.; Tissut, M.; Ravanel, P. Phototransformation of the insecticide fipronil: identification of novel photoproducts and evidence for an alternative pathway of photodegradation. Environ. Sci. Technol. 2006, 40, 4151-4157.
    • (2006) Environ. Sci. Technol , vol.40 , pp. 4151-4157
    • Raveton, M.1    Aajoud, A.2    Willison, J.C.3    Aouadi, H.4    Tissut, M.5    Ravanel, P.6
  • 14
    • 7044260298 scopus 로고    scopus 로고
    • Dynamics of fipronil residue in vegetable-field ecosystem
    • Pei, Z.; Yitong, L.; Baofeng, L.; Gan, J. J. Dynamics of fipronil residue in vegetable-field ecosystem. Chemosphere 2004, 57, 1691-1696.
    • (2004) Chemosphere , vol.57 , pp. 1691-1696
    • Pei, Z.1    Yitong, L.2    Baofeng, L.3    Gan, J.J.4
  • 15
    • 1842689852 scopus 로고    scopus 로고
    • Microbial degradation of fipronil in clay loam soil
    • Zhu, G.; Wu, H.; Guo, J.; Kimaro, F. M. E. Microbial degradation of fipronil in clay loam soil. Water Air Soil Pollut. 2004, 153, 35-44.
    • (2004) Water Air Soil Pollut , vol.153 , pp. 35-44
    • Zhu, G.1    Wu, H.2    Guo, J.3    Kimaro, F.M.E.4
  • 16
    • 0036434758 scopus 로고    scopus 로고
    • Laboratory and field studies on the degradation of fipronil in a soil
    • Ying, G. G.; Kookana, R. Laboratory and field studies on the degradation of fipronil in a soil. Aust. J. Soil Res. 2002, 40, 1095-1102.
    • (2002) Aust. J. Soil Res , vol.40 , pp. 1095-1102
    • Ying, G.G.1    Kookana, R.2
  • 17
    • 0034827405 scopus 로고    scopus 로고
    • Fate of a phenylpyrazole in vegetation and soil under tropical field conditions
    • Fenet, H.; Beltran, E.; Gadji, B.; Cooper, J. F.; Coste, C. M. Fate of a phenylpyrazole in vegetation and soil under tropical field conditions. J. Agric. Food. Chem. 2001, 49, 1293-1297.
    • (2001) J. Agric. Food. Chem , vol.49 , pp. 1293-1297
    • Fenet, H.1    Beltran, E.2    Gadji, B.3    Cooper, J.F.4    Coste, C.M.5
  • 18
    • 0037207524 scopus 로고    scopus 로고
    • ICON rice seed treatment toxicity to crayfish (Procambrus clarkii) in experimental rice paddies
    • Biever, R. C.; Hoberg, J. R.; Jacobson, B.; Dionne, E.; Sulaiman, M.; McCahon, P. ICON rice seed treatment toxicity to crayfish (Procambrus clarkii) in experimental rice paddies. Environ. Toxicol. Chem. 2003, 22, 167-174.
    • (2003) Environ. Toxicol. Chem , vol.22 , pp. 167-174
    • Biever, R.C.1    Hoberg, J.R.2    Jacobson, B.3    Dionne, E.4    Sulaiman, M.5    McCahon, P.6
  • 19
    • 0031949119 scopus 로고    scopus 로고
    • Behaviour of fipronil in soil under Sahelian Plain field conditions
    • Bobe, A.; Cooper, J. F.; Coste, C. M.; Muller, M. A. Behaviour of fipronil in soil under Sahelian Plain field conditions. Pestic. Sci. 1998, 52, 275-281.
    • (1998) Pestic. Sci , vol.52 , pp. 275-281
    • Bobe, A.1    Cooper, J.F.2    Coste, C.M.3    Muller, M.A.4
  • 20
    • 0001301914 scopus 로고    scopus 로고
    • Kinetics and mechanisms of abiotic degradation of fipronil (hydrolysis and photolysis)
    • Bobe, A.; Meallier, P.; Cooper, J. F.; Coste, C. M. Kinetics and mechanisms of abiotic degradation of fipronil (hydrolysis and photolysis). J. Agric. Food. Chem. 1998, 46, 2834-2839.
    • (1998) J. Agric. Food. Chem , vol.46 , pp. 2834-2839
    • Bobe, A.1    Meallier, P.2    Cooper, J.F.3    Coste, C.M.4
  • 21
    • 0034850016 scopus 로고    scopus 로고
    • Abiotic processes influencing fipronil and desthiofipronil dissipation in California, USA, rice fields
    • Ngim, K. K.; Crosby, D. G. Abiotic processes influencing fipronil and desthiofipronil dissipation in California, USA, rice fields. Environ. Toxicol. Chem. 2001, 20, 972-977.
    • (2001) Environ. Toxicol. Chem , vol.20 , pp. 972-977
    • Ngim, K.K.1    Crosby, D.G.2
  • 22
    • 0037467040 scopus 로고    scopus 로고
    • Fipronil metabolism and dissipation in a simplified aquatic ecosystem
    • Aajoud, A.; Ravanel, P.; Tissut, M. Fipronil metabolism and dissipation in a simplified aquatic ecosystem. J. Agric. Food Chem. 2003, 51, 1347-1352.
    • (2003) J. Agric. Food Chem , vol.51 , pp. 1347-1352
    • Aajoud, A.1    Ravanel, P.2    Tissut, M.3
  • 24
    • 30344460003 scopus 로고    scopus 로고
    • Probing the enantioselectivity of chiral pesticides
    • Garrison, A. W. Probing the enantioselectivity of chiral pesticides. Environ. Sci. Technol. 2006, 40, 16-23.
    • (2006) Environ. Sci. Technol , vol.40 , pp. 16-23
    • Garrison, A.W.1
  • 25
    • 0036357799 scopus 로고    scopus 로고
    • Enantiomeric enrichment of chiral pesticides in the environment
    • Hegeman, W. J. M.; Laane, R. W. P. M. Enantiomeric enrichment of chiral pesticides in the environment. Rev. Environ. Contam. Toxicol. 2002, 173, 85-116.
    • (2002) Rev. Environ. Contam. Toxicol , vol.173 , pp. 85-116
    • Hegeman, W.J.M.1    Laane, R.W.P.M.2
  • 26
    • 23944465656 scopus 로고    scopus 로고
    • Acute enantioselective toxicity of fipronil and its desulfinyl photoproduct to Ceriodaphnia dubia
    • Konwick, B. J.; Fisk, A. T.; Garrison, A. W.; Avants, J. K.; Black, M. C. Acute enantioselective toxicity of fipronil and its desulfinyl photoproduct to Ceriodaphnia dubia. Environ. Toxicol. Chem. 2005, 24, 2350-2355.
    • (2005) Environ. Toxicol. Chem , vol.24 , pp. 2350-2355
    • Konwick, B.J.1    Fisk, A.T.2    Garrison, A.W.3    Avants, J.K.4    Black, M.C.5
  • 27
    • 33646353437 scopus 로고    scopus 로고
    • Bioaccumulation, biotransformation, and metabolite formation of fipronil and chiral legacy pesticides in rainbow trout
    • Konwick, B. J.; Garrison, A. W.; Black, M. C.; Avants, J. K.; Fisk, A. T. Bioaccumulation, biotransformation, and metabolite formation of fipronil and chiral legacy pesticides in rainbow trout. Environ. Sci. Technol. 2006, 40, 2930-2936.
    • (2006) Environ. Sci. Technol , vol.40 , pp. 2930-2936
    • Konwick, B.J.1    Garrison, A.W.2    Black, M.C.3    Avants, J.K.4    Fisk, A.T.5
  • 28
    • 0026719882 scopus 로고
    • Chromatographic separation of the enantiomers of marine pollutants. Part 5: Enantioselective degradation of phenoxycarboxylic acid herbicides by marine microorganisms
    • Ludwig, R.; Gunkel, W.; Huhnerfuss, H. Chromatographic separation of the enantiomers of marine pollutants. Part 5: enantioselective degradation of phenoxycarboxylic acid herbicides by marine microorganisms. Chemosphere 1992, 24, 1423-1429.
    • (1992) Chemosphere , vol.24 , pp. 1423-1429
    • Ludwig, R.1    Gunkel, W.2    Huhnerfuss, H.3
  • 29
    • 0028132696 scopus 로고
    • Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy) propionic acid] by mixed and pure bacterial cultures
    • Tett, V. A.; Willetts, A. J.; Lappin-Scott, H. M. Enantioselective degradation of the herbicide mecoprop [2-(2-methyl-4-chlorophenoxy) propionic acid] by mixed and pure bacterial cultures. Microbial. Ecol. 1994, 14, 191-200.
    • (1994) Microbial. Ecol , vol.14 , pp. 191-200
    • Tett, V.A.1    Willetts, A.J.2    Lappin-Scott, H.M.3
  • 30
    • 0242600601 scopus 로고    scopus 로고
    • Changes in enantiomeric fractions during microbial reductive dechlorination of PCB132, PCB149, and Aroclor 1254 in Lake Hartwell sediment microcosms
    • Pakdeesusuk, U.; Jones, W. J.; Lee, C. M.; Garrison, A. W.; O'Niell, W. L.; Freedman, D. L.; Coates, J. T.; Wong, C. S. Changes in enantiomeric fractions during microbial reductive dechlorination of PCB132, PCB149, and Aroclor 1254 in Lake Hartwell sediment microcosms. Environ. Sci. Technol. 2003, 37, 1100-1107.
    • (2003) Environ. Sci. Technol , vol.37 , pp. 1100-1107
    • Pakdeesusuk, U.1    Jones, W.J.2    Lee, C.M.3    Garrison, A.W.4    O'Niell, W.L.5    Freedman, D.L.6    Coates, J.T.7    Wong, C.S.8
  • 31
    • 0035158670 scopus 로고    scopus 로고
    • Enantiomeric composition of chiral polychlorinated biphenyl atropisomers in aquatic bed sediment
    • Wong, C. S.; Garrison, A. W.; Foreman, W. T. Enantiomeric composition of chiral polychlorinated biphenyl atropisomers in aquatic bed sediment. Environ. Sci. Technol. 2001, 35, 33-39.
    • (2001) Environ. Sci. Technol , vol.35 , pp. 33-39
    • Wong, C.S.1    Garrison, A.W.2    Foreman, W.T.3
  • 32
    • 0035890347 scopus 로고    scopus 로고
    • Interpreting nonracemic residues of chiral organochlorines using naturally contaminated fish
    • Vetter, W.; Smalling, K. L.; Maruya, K. A. Interpreting nonracemic residues of chiral organochlorines using naturally contaminated fish. Environ. Sci. Technol. 2001, 35, 4444-4448.
    • (2001) Environ. Sci. Technol , vol.35 , pp. 4444-4448
    • Vetter, W.1    Smalling, K.L.2    Maruya, K.A.3
  • 34
    • 0033135473 scopus 로고    scopus 로고
    • Using enantiomers to trace pesticide emissions
    • Bidleman, T. F.; Falconer, R. L. Using enantiomers to trace pesticide emissions. Environ. Sci. Technol. 1999, 33, 206-209.
    • (1999) Environ. Sci. Technol , vol.33 , pp. 206-209
    • Bidleman, T.F.1    Falconer, R.L.2
  • 37
    • 0028262612 scopus 로고
    • Partitioning and speciation of solid phase Fe in saltmarsh sediments
    • Kostka, J. E.; Luther, G. W. Partitioning and speciation of solid phase Fe in saltmarsh sediments. Geochim. Cosmochim. Acta 1994, 58, 1701-1710.
    • (1994) Geochim. Cosmochim. Acta , vol.58 , pp. 1701-1710
    • Kostka, J.E.1    Luther, G.W.2
  • 38
    • 84944816274 scopus 로고
    • Spectrophotometric determination of hydrogen sulfide in natural waters
    • Cline, J. D. Spectrophotometric determination of hydrogen sulfide in natural waters. Limnol. Oceanogr. 1969, 14, 454-458.
    • (1969) Limnol. Oceanogr , vol.14 , pp. 454-458
    • Cline, J.D.1
  • 39
    • 0037080148 scopus 로고    scopus 로고
    • Environmental behavior of the chiral acetamide pesticide metalaxyl: Enantioselective degradation and chiral stability in soil
    • Buser, H. R.; Muller, M. D.; Poiger, T.; Balmer, M. E. Environmental behavior of the chiral acetamide pesticide metalaxyl: enantioselective degradation and chiral stability in soil. Environ. Sci. Technol. 2002, 36, 221-226.
    • (2002) Environ. Sci. Technol , vol.36 , pp. 221-226
    • Buser, H.R.1    Muller, M.D.2    Poiger, T.3    Balmer, M.E.4
  • 40
    • 23844481767 scopus 로고    scopus 로고
    • Application of capillary electrophoresis to study the enantioselective transformation of five chiral pesticides in aerobic soil slurries
    • Jarman, J. L.; Jones, W. J.; Howell, L. A.; Garrison, A. W. Application of capillary electrophoresis to study the enantioselective transformation of five chiral pesticides in aerobic soil slurries. J. Agric. Food Chem. 2005, 53, 6175-6182.
    • (2005) J. Agric. Food Chem , vol.53 , pp. 6175-6182
    • Jarman, J.L.1    Jones, W.J.2    Howell, L.A.3    Garrison, A.W.4
  • 41
    • 0037782336 scopus 로고    scopus 로고
    • Enantioselective degradation of metalaxyl in soils: Chiral preference changes with soil pH
    • Buerge, I. J.; Poiger, T.; Muller, M. D.; Buser, H. R. Enantioselective degradation of metalaxyl in soils: chiral preference changes with soil pH. Environ. Sci. Technol. 2003, 37, 2668-2674.
    • (2003) Environ. Sci. Technol , vol.37 , pp. 2668-2674
    • Buerge, I.J.1    Poiger, T.2    Muller, M.D.3    Buser, H.R.4
  • 42
    • 0004249702 scopus 로고    scopus 로고
    • 2nd ed, John Wiley & Sons: New York
    • Tate, R. L. Soil Microbiology, 2nd ed.; John Wiley & Sons: New York, 2000.
    • (2000) Soil Microbiology
    • Tate, R.L.1
  • 43
    • 0033613451 scopus 로고    scopus 로고
    • Influence of environmental changes on degradation of chiral pollutants in soils
    • Lewis, D. L.; Garrison, A. W.; Wommack, K. E.; Whittemore, A.; Steudler, P.; Melillo, J. Influence of environmental changes on degradation of chiral pollutants in soils. Nature 1999, 401, 898-901.
    • (1999) Nature , vol.401 , pp. 898-901
    • Lewis, D.L.1    Garrison, A.W.2    Wommack, K.E.3    Whittemore, A.4    Steudler, P.5    Melillo, J.6


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