Bifenthrin (BF) is a chiral pesticide with two enantiomers. In this work, its stereoselective degradation was investigated in plants and domesticated active sludge. Considering that the degradation to pesticides of plants was effected by external conditions, hence, nanometer materials (gothite) were added into soil to explore the effect of sorption on enantioselectivity in degradation of BF. The microbial community that was responsible for BF-biodegrading in active sludge was studied by polymerase chain reaction and denaturing gradient gel electrophoresis (PCR-DGGE). In plant researches, chiral difference was discovered in the degradation of pesticides that onions resulted in. The existence of gothite in soil not only reduced the amount of BF that plants uptake from the environment, but it also enlarged the chiral difference during the process, indicating that the absorption of gothite to pesticides had enantioselectivity, which may be generated by that adsorption site where BF combined with gothite located in the chiral center of the pesticide. In studies of sludge, BF can be effectively degraded and decline of both isomers followed first-order kinetics. However, there was no obvious stereoselective degradation in domesticated sludge. The analysis of DGGE revealed that active sludge maintained the rich microbial community in the whole process (H >3). The H index increased in the early domestication, which may because BF had no direct toxicity to the bacteria. The bacteria were able to degrade the small dose of the pesticide and absorbed it as nutrition. The sequence results demonstrated that the variety of bacteria grew, instead of Acidobacteria, Betaproteobacteria, Sphingobacteriia and Alphaproteobacteria, Flavobacteria also appearing in sludge after domestication.