PMID: 18200855Jan 19, 2008Paper

Enantioselective microbial transformation of the phenylpyrazole insecticide fipronil in anoxic sediments

Environmental Science & Technology
W Jack JonesArthur W Garrison

Abstract

Fipronil, a chiral insecticide, was biotransformed initially to fipronil sulfide in anoxic sediment slurries following a short lag period. Sulfidogenic or methanogenic sediments transformed fipronil with half-lives of approximately 35 and 40 days, respectively. In all microbially active sediment slurries tested, the transformation of fipronil to fipronil sulfide was enantioselective. In the sulfidogenic sediment slurry, the enantiomeric fraction (EF) of fipronil decreased from an initial racemic EF value of 0.46 to a value of 0.22 during the incubation period of active fipronil transformation, indicating preferential transformation of the S-(+)-enantiomer. A previously unidentified product, 5-amino1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-(trifluoromethylthio)-1-H-pyrazole-3-carboxyamide, or fipronil sulfide-amide, was detected in the sulfidogenic slurries and coincided with the loss of fipronil sulfide. Biota from methanogenic freshwater sediment slurries also transformed fipronil enantioselectively but with a preference for the R-(-)-enantiomer. In all microbially inhibited (autoclaved) sediment slurries tested, no changes in the enantiomeric fractions of fipronil were observed and only low levels (< 5% of the added fipro...Continue Reading

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Citations

Aug 10, 2007·Archives of Environmental Contamination and Toxicology·W Aaron WilsonMarsha C Black
Apr 17, 2012·Journal of Hazardous Materials·Tiantian LiuZhiqiang Zhou
Apr 10, 2012·Journal of Hazardous Materials·Huijun LiuJiang Shi
Sep 23, 2014·Environmental Toxicology and Chemistry·Toshinari SuzukiDai Nakae
Jan 12, 2010·Environmental Pollution·Premasis SukulMichael Spiteller
Apr 10, 2010·Environmental Pollution·Jing YeWeiping Liu
May 6, 2009·Toxicological Sciences : an Official Journal of the Society of Toxicology·Silas W Smith
Jan 3, 2013·Medical and Veterinary Entomology·K IngenloffR M Poché
Aug 30, 2008·Journal of Agricultural and Food Chemistry·Kunde LinJay Gan
Jun 11, 2009·Journal of Agricultural and Food Chemistry·Jinling DiaoZhiqiang Zhou
Aug 28, 2014·Environmental Science & Technology·Xiyun CaiJingwen Chen

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