Bioaccumulation, biotransformation, and metabolite formation of fipronil and chiral legacy pesticides in rainbow trout
Environmental Science and Technology
To assess the fate of current-use pesticides, it is important to understand their bioaccumulation and biotransformation by aquatic biota. We examined the dietary accumulation and enantioselective biotransformation of the chiral current-use pesticide fipronil, along with a mixture of selected chiral [α-hexachlorocyclohexane(α-HCH), heptachlor epoxide (HEPX), polychlorinated biphenyls (PCBs) 84,132,174, o,p′-DDT, and o,p′-DDD] and nonchiral (p,p′-DDT, p,p′-DDD) organochlorine compounds in juvenile rainbow trout (Oncorhynchus mykiss). Fish rapidly accumulated all compounds, as measured in the carcass (whole body minus liver and GI tract) during the 32 d uptake phase, which was followed by varying elimination rates of the chemicals (half-lives (t1/2s) ranging from 0.6 d for fipronil to 77.0 d for PCB 174) during the 96 d depuration period. No biotransformation was observed for α-HCH, HEPX, PCB 174, o,p′-DDT, or o,p′-DDD based on consistent enantiomeric fractions (EFs) in the fish and their t 1/2s falling on a log Kow - log t1/2 relationship established for recalcitrant contaminants in fish. p,p′-DDT and PCBs 84 and 132 were biotransformed based on the former's t1/2 position below the log Kow - log t1/2 relationship, and the PCBs change in EF. Fipronil was rapidly biotransformed, based on a change in EF, a t1/2s that fell below the log Kow - log t 1/2 relationship, which accounted for 88% of its elimination, and the rapid formation of fipronil sulfone, a known metabolite. Fipronil sulfone was found to persist longer (t1/2 ∼ 2 d) than its parent compound fipronil (t1/2 ∼ 0.6 d) and needs to be considered in fate studies of fipronil. This research demonstrates the utilities of the log K ow - log t1/2 relationship as a mechanistic tool for quantifying biotransformation and of chiral analysis to measure biotransformation in fish. © 2006 American Chemical Society.
Konwick, Brad J.; Garrison, Arthur W.; Black, Marsha C.; Avants, Jimmy K.; and Fisk, Aaron T.. (2006). Bioaccumulation, biotransformation, and metabolite formation of fipronil and chiral legacy pesticides in rainbow trout. Environmental Science and Technology, 40 (9), 2930-2936.