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Enantioselectivity occurs widely in the environmental behaviors and toxicity of chiral contaminations such as pesticides. However，the investigation on the enantioselective toxicology mechanisms remains very limited especially in food safety. In this study，we used fenamiphos and malathion as the models of organophosphate insecticide to study the enantioselectivity in aquatic toxicity and the inhibition potential toward acetylcholinesterase（AChE） in rat pheochromocytoma 12（PC 12） cell line. Furthermore，we carried out molecular docking to explain the mechanisms of enantioselective toxicity of these two chemicals. This study made auspices in understanding the impact of stereochemistry on assessment of toxicological effects in food safety. Given the widespread use of chiral pesticides，a more comprehensive understanding of the significances of enantioselectivity is imperative for improving food safety assessment and regulation of these pesticides.