The pyrethroid (±)-lambda-cyhalothrin enantioselective biodegradation by a bacterial consortium

Abstract

Chiral pesticides have been used in agriculture, including (±)-lambda-cyhalothrin ((±)-LC), which is a pyrethroid insecticide widely employed on crops for protection against different types of insects. However, enantioselectivity is poorly studied in biodegradation processes. Therefore, the (±)-LC enantioselective biodegradation by bacteria from Brazilian savannah was reported in this study with a validated analytical method. All bacterial strains biodegraded (±)-LC with different efficiencies. Residual concentrations of LC (3.7–43.1% of biodegradation) and its enantiomeric excesses (0–27% ee) were determined. Additionally, the formation of the main biodegradation metabolite 3-phenoxybenzoic acid was also quantified. A Bacillus consortium composed of the three most efficient strains biodegraded more LC than any isolated strain solely employed in this work, showing that the use of a consortium is an interesting approach. In addition, 13 metabolites were identified and a biodegradation pathway with biochemical reactions of hydrolysis, reduction, esterification, amidation, elimination and group transfer were proposed, confirming the bioremediation potential of these strains. The LC stereoisomer with the highest insecticidal activity (1R,3R,αS-enantiomer, also known as gamma-cyhalothrin) was preferentially biodegraded by the studied bacteria. Therefore, crops protection with gamma-cyhalothrin, which can be applied in lower concentrations than (±)-LC because it is a more effective product against insects, may also be biodegraded faster than the racemic mixture in the environment, decreasing the toxic effects on non-target organisms.