Biodegradation of Chiral Flufiprole in Chlorella pyrenoidosa: Kinetics, Transformation Products, and Toxicity Evaluation.

Pesticide pollution of surface water represents a considerable risk for algae and thus affects the structure and stability of aquatic ecosystems. To investigate the risk of flufiprole to phytoplankton, the digestion and uptake of flufiprole as well as the toxic effects of flufiprole enantiomers and the six metabolites to Chlorella pyrenoidosa were investigated. Flufiprole enantiomers were mainly metabolized to flufiprole amide and detrifluoromethylsulfinyl flufiprole in culture medium, while various metabolites were formed in algae, notably the amide derivative and fipronil. Chlorella pyrenoidosa showed a strong absorption capacity for the flufiprole series. The EC50 values (96 h) indicated that fipronil was the most toxic compound, approximately 5 times as toxic as rac-flufiprole. R-flufiprole was more toxic than S-flufiprole. The contents of chlorophylls, malondialdehyde (MDA), reactive oxygen species (ROS), and total antioxidant capacity (T-AOC) were significantly altered by the chemicals in most cases, especially fipronil. Our results supported the potential detrimental effect of the metabolites of flufiprole on algae.