Fipronil: usos, características farmacológicas e toxicológicas
Palavras-chave:
Ectoparasiticida, Fipronil, Praguicida, Toxicidade
Resumo
O fipronil é um praguicida fenilpirazol amplamente empregado com inseticida na agricultura e para o combate de ectoparasitas em medicina veterinária. Considerando esse amplo uso, é importante conhecer as principais características farmacológicas, bem como a toxicidade dessa substância. Neste artigo são abordados os seguintes tópicos: os usos desse praguicida, suas propriedades físico-químicas, sua degradação no meio ambiente, biotransformação e eliminação em mamíferos, seu mecanismo de ação e sua toxicidade.Referências
AGROFIT. Sistema de Agrotóxicos Fitossanitários. Regent 800 WG: Relatório de produtos formulados. Ministério da Agricultura, Pecuária e Abastecimento. Brasília, 2007. 3p.
ANVISA – Agência Nacional de Vigilância Sanitária. Monografia de agrotóxicos: F43-Fipronil. Disponível pelo site:. Acesso em: 10 jan. 2016.
BEGGEL, S.; WERNER, I.; CONNON, R. E.; GEIST, J.P. Sublethal toxicity of commercial insecticide formulations and their active ingredients to larval fathead minnow (Pimephales promelas). Science of the Total Environment, v. 408, p. 3169-3175, 2010. doi: 10.1016/j.scitotenv.2010.04.004.
BOBÉ, A.; MEALLIER, P.; COOPER, J.; COSTE, C. M. Kinetics and mechanisms of abiotic degradation of fipronil (hydrolysis and photolysis). Journal of Agricultural and Food Chemistry, v. 46, p. 2834-2839, 1998. doi: 10.1021/jf970874d
CABONI, P.; SAMMELSON, R. E.; CASIDA, J. E. Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil. The Journal of Agricultural and Food Chemistry, v. 51, p. 7055-7061, 2003. doi: 10.1021/jf030439l
CHEBIB, M.; HANRAHAN, J. R.; KUMAR, R. J.; MEWETT, K. N.; MORRISS, G.; WOOLLER, S.; JOHNSTON, G. A. R. (3-Aminocyclopentyl) methylphosphonic acids: novel GABAc receptor antagonists. Neuropharmacology, v. 52, p. 779-787, 2007. doi:10.1016/j.neuropharm.2006.09.014
COCHET, P.; BIRCKEL, P.; BROMET-PETIT, M.; BROMET, N.; WEIL, A. Skin distribution of fipronil by microautoradiography following topical administration to the beagle dog. European Journal of Drug Metabolism and Pharmacokinetics, v.22, n.3, p.211-216.
COMPÊNDIO DE DEFENSIVOS AGRÍCOLA. 8.ed, São Paulo, Andrei. 2009.
CONNELLY, P. Environmental fate of fipronil. In: Environmental Monitoring Branch. California Environmental Protection Agency. Dec. 2001. 17p.
DPR. Department of Pesticide Regulation. Pesticide chemistry database. Department of Pesticide Regulation, Sacramento-California. Dissipation. Rhône -Poulenc Agricultural Limited. Data Package ID No. 169043-45 DPR Document No.52062-240 Pt.1, 2001.
DURHAM, E.W.; SIEGFRIED, B. D.; SCHARF, M. E. In vivo and in vitro metabolism of fipronil by larvae of the European corn borer Ostrinia nubilalis. Pest Management Science, v. 58, n. 8, p. 799-804, 2002. doi: 10.1002/ps.523.
EL HASSANI, A. K. E.; DUPUIS, J. P.; GAUTHIER, M.; ARMENGAUD, C. Glutamatergic and GABAergic effects of fipronil on olfactory learning and memory in the honeybee. Invertebrate Neuroscience, v. 9, n. 2, p. 91-100, 2009. doi: 10.1007/s10158-009-0092-z
GUNASEKARA, A. S.; TRUONG, T.; GOH, K. S.; SPURLOCK, F.; TJEERDEMA, R. Environmental fate and toxicology of fipronil. Journal of Pesticide Science, v. 32, n. 3, p.189-199. doi: 10.1584/jpestics.r07-02, 2007a.
GUNASEKARA, A. S.; TROUNG, T. Environmental Fate of Fipronil. In: California Environmental Protection Agency. Environmental Monitoring Branch. 2007b. 28.p.
IBAMA – Instituto Brasileiro do Meio Ambiente e dos Recursos Naturais Renováveis. Boletim de comercialização de agrotóxicos e afins: histórico de vendas 2000 a 2012. p.1-42, 2012.
IKEDA, T.; ZHAO, X.; NAGATA, K.; KONO, Y.; SHONO, T.; YEH, J. Z.; NARAHASHI, T. Fipronil modulation of γ-aminobutyric acida receptors in rat dorsal root ganglion neurons. Journal of Pharmacology and Experimental Therapeutics, v. 296, n. 3, p.914-921, 2000.
IKEDA, T.; NAGATA, K.; KONO, Y.; YEH, J. Z.; NARAHASHI, T. Fipronil Modulation of GABA A receptor single-channel currents. Pest Management Science, v. 60, n.5, p. 487-492. 2004. doi: 10.1002/ps.830.
IPCS/INCHEM – International Programme on Chemical Safety. Fipronil. Pesticide Residues in Food – 1997. 1997. Disponível em:
v097pr09.htm>. Acesso em: 22 de abr. 2012.
ISLAM, R.; LYNCH, J. Mechanism of action of the insecticides, lindane and fipronil, on glycine receptor chloride channels. British Journal of Pharmacology, v. 165, p. 2707-2720, 2012. doi: 10.1111/j.1476-5381.2011.01722.x
LE FAOUNDER, J. L.; BICHON, E.; BRUNSCHWIG, P.; LANDELLE, R.; ANDRE, F.; LE BIZEC, B. Transfer assessment of fipronil residues from feed to cow milk. Talanta. v. 73, p. 710-717. 2007. doi: 10.1016/j.talanta.2007.04.061
MAGALHÃES, J. Z.; UDO, M. S.; SÁNCHEZ-SARMIENTO, A. M.; CARVALHO, M. P.; BERNARDI, M. M.; SPINOSA, H. S. Prenatal exposure to fipronil disturbs maternal aggressive behavior in rats. Neurotoxicology and Teratology, v. 52, p.11-16, 2015. doi: 10.1016/j.ntt.2015.09.007
MARTINS, A. P. Efeitos neurocomportamentais do fipronil administrado em dose única a ratos. 2009. 86f. Tese (Mestrado em Ciências) – Programa de Patologia Experimental e Comparada, Faculdade de Medicina Veterinária e Zootecnia, Universidade de São Paulo, São Paulo. 2009.
MASUTTI, C. S. M.; MERMUT, A. R. Degradation of fipronil under laboratory conditions in a tropical soil from Sirinhaém Pernambuco, Brazil. Journal of Environmental Science and Health, v. 42, parte B, p. 33-43, 2007. doi: 10.1080/10934520601015446
MOHAMED, F.; SENARATHNA, L.; PERCY, A.; ABEYEWARDENE, M.; EAGLESHAM, G.; CHENG, R.; AZHER, S.; HITTARAGE, A.; DISSANAYAKE, W.; SHERIFF, M. H.; DAVIES, W.; BUCKLEY, N. A.; EDDLESTON, M. Acute human self-poisoning with N-Phenylpyrazole insecticide fipronil – a GABAA – gated chloride channel blocker. Journal of Clinical Toxicology, v. 42, n. 7, p. 955-963, 2004.
MOHLER, H.; FRITSCHY, J. M.; CRESTANI, F.; HENSCH, T.; RUDOLPH, U. Specific GABA(A) circuits in brain development and therapy. Biochemical Pharmacology, v.15, n.8, p.1685-1690, 2004. doi: 10.1016/j.bcp.2004.07.025
MURILLO, L.; HAMON, A.; ES-SALAH-LAMOUREUX, Z.; ITIER, V.; QUINCHARD, S.; LAPIED, B. Inhibition of protein kinase C decreases sensitivity of GABA receptor subtype to fipronil insecticide in insect neurosecretory cells. Neurotoxicology, v. 32, p. 828-835, 2011. http://dx.doi.org/10.1016/j.neuro.2011.05.015
NARAHASHI, T.; ZHAO, X.; IKEDA, T.; NAGATA, K.; YEH, J. Z. Differential actions of insecticides on target sites: basis for selective toxicity. Human experimental toxicology, v. 26, n. 4, p.-361-366, 2007. doi: 10.1177/0960327106078408
NCAP. Northwest Coalition for Alternatives to Pesticide. Fipronil. Journal of Pesticide Reform. v. 25, n. 1, p.10-15, 2005
NCAMP. National Coalition Against the Misuse of Pesticides. Chemical watch gactsheet: Fipronil. Disponível em:. Acesso em: 21 fev. 2016
NPIC. National Pesticide Information Center. Fipronil. Oregon State University and the U.S. Environmental Protection Agency. 2009. Disponível em:. Acesso em 17 fev. 2016.
OHI, M.; DALSENTER, P. R.; ANDRADE, A. J.; NASCIMENTO, A. J. Reproductive adverse effects of fipronil in Wistar rats. Toxicology Letters, v.146, p. 121-127. 2004. http://dx.doi.org/10.1016/j.toxlet.2003.08.008
PEIXOTO, A. S.; COELHO, M. C. O. C.; BARBOSA, M. B. Atualidades em tratamentos utilizados em dermatopatias de cães – Revisão. Revista de Educação Continuada do Conselho Regional de Medicina Veterinária de São Paulo, v. 5, fascículo 1, p. 14 - 24. 2002.
RAVETON, M.; AAJOUD, A.; WILLISON, J.; CHERIFI, M.; TISSUT, M.; RAVANEL, P. Soil distribution of fipronil and its metabolites originating from a seed-coated formulation. Chemosphere, v. 69, p. 1124-1129, 2007. doi: 10.1016/j.chemosphere.2007.03.063
RHÔNE-POULENC. Atelier International Fipronil/lutte antiacridienne. Lyon: Rhône-Poulenc Agrochimie, 1995.
STARK, J. D.; VARGAS, R. I. Toxicity and hazard assessment of fipronil to Daphnia pulex. Ecotoxicology and Environmental Safety, v. 62, p. 11-16, 2005. doi: 10.1016/j.ecoenv.2005.02.011
SZEGEDI, V.; BÁRDOS, G.; DÉTÁRI, L.; TÓTH, A.; BANCZEROWSKI-PELYHE, I.; VILÁGI, I. Transient alterations in neuronal and behavioral activity following bensultap and fipronil treatment in rats. Toxicology, v. 214, p.67-76, 2005. doi: 10.1016/j.tox.2005.05.023
TERÇARIOL, P. R. G. Avaliação neurocomportamental de ratos expostos agudamente ao fipronil – Influência de Diazepam e Flumazenil. 2007. 78f. Tese (Mestrado em Ciência Veterinária) – Faculdade de Medicina Veterinária e Zootecnia, Universidade Estadual Paulista Julio de Mesquita Filho, UNESP, Botucatu. 2007.
TINGLE, C. C. D.; ROTHER, J. A.; DEWHURST, C. F.; LAUER, S.; KING, W. J. Health and environmental effects of fipronil. Briefing paper. Pesticide Action Network UK. P. 1-30. 2000.
TINGLE, C. C. D.; ROTHER, J. A.; DEWHURST, C. F.; LAUER, S.; KING, W. J. Fipronil: environmental fate, ecotoxicology and human health concerns. Reviews of Environmental Contamination and Toxicology, v. 176, p. 1–66, 2003.
UDO, M. S.; SANDINI, T. M.; REIS, T. M.; BERNARDI, M. M.; SPINOSA, H. S. Prenatal exposure to a low fipronil dose disturbs maternal behavior and reflex development in rats. Neurotoxicology and teratology, v. 45, p. 27-33, 2014. doi: 10.1016/j.ntt.2014.05.010
USEPA. Environmental Protection Agency. New Pesticide Fact Sheet. PB96-181516.EPA737-F-96-005. U.S. EPA Office of Prevention, Pesticides and Toxic Substances, p1-10, 1996.
USEPA – United States Environmental Protection Agency. Environmental fate of fipronil. Washington: U.S.EPA Office of Prevention Pesticides and Toxic Substances, 2001. 17p. Disponível em:. Acesso em: 14 fev. 2016.
ZHAO, X.; YEH, J. Z.; SALGADO, V. L.; NARAHASHI, T. Fipronil is a potente open channel blocker of glutamate –activated chloride channels in cockroach neurons. The Journal of Pharmacology and Experimental Therapeutics, v.310, n.1, p. 192-201, 2004. doi: 10.1124/jpet.104.065516
ZHAO, X.; YEH, J. Z.; SALGADO, V. L.; NARAHASHI, T. Sulfone metabolite of fipronil blocks γ-aminobutyric acid- and glutamate-activated chloride channels in mammalian and insect neurons. The Journal of Pharmacology and Experimental Therapeutics, v.314, n.1, p. 363 – 373, 2005. doi: https://doi.org/10.1124/jpet.104.077891
ZHU, G.; WU, H.; GUO, J.; KIMARO, F. M. E. Microbial degradation of fipronil in clay loam soils. Water Air Soil Pollution, v. 153, p. 35-44, 2004. doi: 10.1023/B:WATE.0000019928.67686.b1
ANVISA – Agência Nacional de Vigilância Sanitária. Monografia de agrotóxicos: F43-Fipronil. Disponível pelo site:
BEGGEL, S.; WERNER, I.; CONNON, R. E.; GEIST, J.P. Sublethal toxicity of commercial insecticide formulations and their active ingredients to larval fathead minnow (Pimephales promelas). Science of the Total Environment, v. 408, p. 3169-3175, 2010. doi: 10.1016/j.scitotenv.2010.04.004.
BOBÉ, A.; MEALLIER, P.; COOPER, J.; COSTE, C. M. Kinetics and mechanisms of abiotic degradation of fipronil (hydrolysis and photolysis). Journal of Agricultural and Food Chemistry, v. 46, p. 2834-2839, 1998. doi: 10.1021/jf970874d
CABONI, P.; SAMMELSON, R. E.; CASIDA, J. E. Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: ethiprole compared with fipronil. The Journal of Agricultural and Food Chemistry, v. 51, p. 7055-7061, 2003. doi: 10.1021/jf030439l
CHEBIB, M.; HANRAHAN, J. R.; KUMAR, R. J.; MEWETT, K. N.; MORRISS, G.; WOOLLER, S.; JOHNSTON, G. A. R. (3-Aminocyclopentyl) methylphosphonic acids: novel GABAc receptor antagonists. Neuropharmacology, v. 52, p. 779-787, 2007. doi:10.1016/j.neuropharm.2006.09.014
COCHET, P.; BIRCKEL, P.; BROMET-PETIT, M.; BROMET, N.; WEIL, A. Skin distribution of fipronil by microautoradiography following topical administration to the beagle dog. European Journal of Drug Metabolism and Pharmacokinetics, v.22, n.3, p.211-216.
COMPÊNDIO DE DEFENSIVOS AGRÍCOLA. 8.ed, São Paulo, Andrei. 2009.
CONNELLY, P. Environmental fate of fipronil. In: Environmental Monitoring Branch. California Environmental Protection Agency. Dec. 2001. 17p.
DPR. Department of Pesticide Regulation. Pesticide chemistry database. Department of Pesticide Regulation, Sacramento-California. Dissipation. Rhône -Poulenc Agricultural Limited. Data Package ID No. 169043-45 DPR Document No.52062-240 Pt.1, 2001.
DURHAM, E.W.; SIEGFRIED, B. D.; SCHARF, M. E. In vivo and in vitro metabolism of fipronil by larvae of the European corn borer Ostrinia nubilalis. Pest Management Science, v. 58, n. 8, p. 799-804, 2002. doi: 10.1002/ps.523.
EL HASSANI, A. K. E.; DUPUIS, J. P.; GAUTHIER, M.; ARMENGAUD, C. Glutamatergic and GABAergic effects of fipronil on olfactory learning and memory in the honeybee. Invertebrate Neuroscience, v. 9, n. 2, p. 91-100, 2009. doi: 10.1007/s10158-009-0092-z
GUNASEKARA, A. S.; TRUONG, T.; GOH, K. S.; SPURLOCK, F.; TJEERDEMA, R. Environmental fate and toxicology of fipronil. Journal of Pesticide Science, v. 32, n. 3, p.189-199. doi: 10.1584/jpestics.r07-02, 2007a.
GUNASEKARA, A. S.; TROUNG, T. Environmental Fate of Fipronil. In: California Environmental Protection Agency. Environmental Monitoring Branch. 2007b. 28.p.
IBAMA – Instituto Brasileiro do Meio Ambiente e dos Recursos Naturais Renováveis. Boletim de comercialização de agrotóxicos e afins: histórico de vendas 2000 a 2012. p.1-42, 2012.
IKEDA, T.; ZHAO, X.; NAGATA, K.; KONO, Y.; SHONO, T.; YEH, J. Z.; NARAHASHI, T. Fipronil modulation of γ-aminobutyric acida receptors in rat dorsal root ganglion neurons. Journal of Pharmacology and Experimental Therapeutics, v. 296, n. 3, p.914-921, 2000.
IKEDA, T.; NAGATA, K.; KONO, Y.; YEH, J. Z.; NARAHASHI, T. Fipronil Modulation of GABA A receptor single-channel currents. Pest Management Science, v. 60, n.5, p. 487-492. 2004. doi: 10.1002/ps.830.
IPCS/INCHEM – International Programme on Chemical Safety. Fipronil. Pesticide Residues in Food – 1997. 1997. Disponível em:
ISLAM, R.; LYNCH, J. Mechanism of action of the insecticides, lindane and fipronil, on glycine receptor chloride channels. British Journal of Pharmacology, v. 165, p. 2707-2720, 2012. doi: 10.1111/j.1476-5381.2011.01722.x
LE FAOUNDER, J. L.; BICHON, E.; BRUNSCHWIG, P.; LANDELLE, R.; ANDRE, F.; LE BIZEC, B. Transfer assessment of fipronil residues from feed to cow milk. Talanta. v. 73, p. 710-717. 2007. doi: 10.1016/j.talanta.2007.04.061
MAGALHÃES, J. Z.; UDO, M. S.; SÁNCHEZ-SARMIENTO, A. M.; CARVALHO, M. P.; BERNARDI, M. M.; SPINOSA, H. S. Prenatal exposure to fipronil disturbs maternal aggressive behavior in rats. Neurotoxicology and Teratology, v. 52, p.11-16, 2015. doi: 10.1016/j.ntt.2015.09.007
MARTINS, A. P. Efeitos neurocomportamentais do fipronil administrado em dose única a ratos. 2009. 86f. Tese (Mestrado em Ciências) – Programa de Patologia Experimental e Comparada, Faculdade de Medicina Veterinária e Zootecnia, Universidade de São Paulo, São Paulo. 2009.
MASUTTI, C. S. M.; MERMUT, A. R. Degradation of fipronil under laboratory conditions in a tropical soil from Sirinhaém Pernambuco, Brazil. Journal of Environmental Science and Health, v. 42, parte B, p. 33-43, 2007. doi: 10.1080/10934520601015446
MOHAMED, F.; SENARATHNA, L.; PERCY, A.; ABEYEWARDENE, M.; EAGLESHAM, G.; CHENG, R.; AZHER, S.; HITTARAGE, A.; DISSANAYAKE, W.; SHERIFF, M. H.; DAVIES, W.; BUCKLEY, N. A.; EDDLESTON, M. Acute human self-poisoning with N-Phenylpyrazole insecticide fipronil – a GABAA – gated chloride channel blocker. Journal of Clinical Toxicology, v. 42, n. 7, p. 955-963, 2004.
MOHLER, H.; FRITSCHY, J. M.; CRESTANI, F.; HENSCH, T.; RUDOLPH, U. Specific GABA(A) circuits in brain development and therapy. Biochemical Pharmacology, v.15, n.8, p.1685-1690, 2004. doi: 10.1016/j.bcp.2004.07.025
MURILLO, L.; HAMON, A.; ES-SALAH-LAMOUREUX, Z.; ITIER, V.; QUINCHARD, S.; LAPIED, B. Inhibition of protein kinase C decreases sensitivity of GABA receptor subtype to fipronil insecticide in insect neurosecretory cells. Neurotoxicology, v. 32, p. 828-835, 2011. http://dx.doi.org/10.1016/j.neuro.2011.05.015
NARAHASHI, T.; ZHAO, X.; IKEDA, T.; NAGATA, K.; YEH, J. Z. Differential actions of insecticides on target sites: basis for selective toxicity. Human experimental toxicology, v. 26, n. 4, p.-361-366, 2007. doi: 10.1177/0960327106078408
NCAP. Northwest Coalition for Alternatives to Pesticide. Fipronil. Journal of Pesticide Reform. v. 25, n. 1, p.10-15, 2005
NCAMP. National Coalition Against the Misuse of Pesticides. Chemical watch gactsheet: Fipronil. Disponível em:
NPIC. National Pesticide Information Center. Fipronil. Oregon State University and the U.S. Environmental Protection Agency. 2009. Disponível em:
OHI, M.; DALSENTER, P. R.; ANDRADE, A. J.; NASCIMENTO, A. J. Reproductive adverse effects of fipronil in Wistar rats. Toxicology Letters, v.146, p. 121-127. 2004. http://dx.doi.org/10.1016/j.toxlet.2003.08.008
PEIXOTO, A. S.; COELHO, M. C. O. C.; BARBOSA, M. B. Atualidades em tratamentos utilizados em dermatopatias de cães – Revisão. Revista de Educação Continuada do Conselho Regional de Medicina Veterinária de São Paulo, v. 5, fascículo 1, p. 14 - 24. 2002.
RAVETON, M.; AAJOUD, A.; WILLISON, J.; CHERIFI, M.; TISSUT, M.; RAVANEL, P. Soil distribution of fipronil and its metabolites originating from a seed-coated formulation. Chemosphere, v. 69, p. 1124-1129, 2007. doi: 10.1016/j.chemosphere.2007.03.063
RHÔNE-POULENC. Atelier International Fipronil/lutte antiacridienne. Lyon: Rhône-Poulenc Agrochimie, 1995.
STARK, J. D.; VARGAS, R. I. Toxicity and hazard assessment of fipronil to Daphnia pulex. Ecotoxicology and Environmental Safety, v. 62, p. 11-16, 2005. doi: 10.1016/j.ecoenv.2005.02.011
SZEGEDI, V.; BÁRDOS, G.; DÉTÁRI, L.; TÓTH, A.; BANCZEROWSKI-PELYHE, I.; VILÁGI, I. Transient alterations in neuronal and behavioral activity following bensultap and fipronil treatment in rats. Toxicology, v. 214, p.67-76, 2005. doi: 10.1016/j.tox.2005.05.023
TERÇARIOL, P. R. G. Avaliação neurocomportamental de ratos expostos agudamente ao fipronil – Influência de Diazepam e Flumazenil. 2007. 78f. Tese (Mestrado em Ciência Veterinária) – Faculdade de Medicina Veterinária e Zootecnia, Universidade Estadual Paulista Julio de Mesquita Filho, UNESP, Botucatu. 2007.
TINGLE, C. C. D.; ROTHER, J. A.; DEWHURST, C. F.; LAUER, S.; KING, W. J. Health and environmental effects of fipronil. Briefing paper. Pesticide Action Network UK. P. 1-30. 2000.
TINGLE, C. C. D.; ROTHER, J. A.; DEWHURST, C. F.; LAUER, S.; KING, W. J. Fipronil: environmental fate, ecotoxicology and human health concerns. Reviews of Environmental Contamination and Toxicology, v. 176, p. 1–66, 2003.
UDO, M. S.; SANDINI, T. M.; REIS, T. M.; BERNARDI, M. M.; SPINOSA, H. S. Prenatal exposure to a low fipronil dose disturbs maternal behavior and reflex development in rats. Neurotoxicology and teratology, v. 45, p. 27-33, 2014. doi: 10.1016/j.ntt.2014.05.010
USEPA. Environmental Protection Agency. New Pesticide Fact Sheet. PB96-181516.EPA737-F-96-005. U.S. EPA Office of Prevention, Pesticides and Toxic Substances, p1-10, 1996.
USEPA – United States Environmental Protection Agency. Environmental fate of fipronil. Washington: U.S.EPA Office of Prevention Pesticides and Toxic Substances, 2001. 17p. Disponível em:
ZHAO, X.; YEH, J. Z.; SALGADO, V. L.; NARAHASHI, T. Fipronil is a potente open channel blocker of glutamate –activated chloride channels in cockroach neurons. The Journal of Pharmacology and Experimental Therapeutics, v.310, n.1, p. 192-201, 2004. doi: 10.1124/jpet.104.065516
ZHAO, X.; YEH, J. Z.; SALGADO, V. L.; NARAHASHI, T. Sulfone metabolite of fipronil blocks γ-aminobutyric acid- and glutamate-activated chloride channels in mammalian and insect neurons. The Journal of Pharmacology and Experimental Therapeutics, v.314, n.1, p. 363 – 373, 2005. doi: https://doi.org/10.1124/jpet.104.077891
ZHU, G.; WU, H.; GUO, J.; KIMARO, F. M. E. Microbial degradation of fipronil in clay loam soils. Water Air Soil Pollution, v. 153, p. 35-44, 2004. doi: 10.1023/B:WATE.0000019928.67686.b1
Publicado
2018-02-26
Como Citar
Magalhães, J. Z., Sandini, T. M., Udo, M. S. B., Fukushima, A. R., & Spinosa, H. de S. (2018). Fipronil: usos, características farmacológicas e toxicológicas. Revista Intertox De Toxicologia, Risco Ambiental E Sociedade, 11(1). https://doi.org/10.22280/revintervol11ed1.344
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