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Oxathiapiprolin is an efficient and chiral fungicide for peronosporomycetes. The enantioselective environmental behavior and ecotoxicity of oxathiapiprolin are still unclear. The enantioselectivity of oxathiapiprolin enantiomers was explored, including their acute toxicity toward aquatic plants (Auxenochlorella pyrenoidosa and Soirodela polyrhiza) along with their influence on photosynthetic pigment production, the acute toxicity and morphological differences for the embryos, larvae and adult stages of zebrafish (Danio rerio), and the degradation in four typical soils (aerobic, anaerobic and sterilized conditions). The enantioselective toxicity of oxathiapiprolin showed that the toxicity of R-oxathiapiprolin was 1.8-2.1 times higher than that of S-oxathiapiprolin toward the two aquatic plants. In particular, the content of photosynthetic pigments decreased significantly stronger after exposure to R-oxathiapiprolin compared with S-oxathiapiprolin. The LC50 values of R-oxathiapiprolin in zebrafish in the different life stages were 1.6-2.1 times higher than those of S-oxathiapiprolin. The zebrafish embryos were most sensitive to the oxathiapiprolin enantiomers. After exposure to R-oxathiapiprolin, zebrafish embryos showed noticeable hatching delays, inhibition or deformation. R-oxathiapiprolin degraded preferentially in all four soils, with an enantiomeric fraction (EF) ranging from 0.28 to 0.42 under aerobic conditions. Enantioselective degradation was not found under anaerobic and sterilized conditions. The enantioselectivity of new chiral pesticides should be fully considered in risk assessments to provide a basis for the development and preparation of pure optical enantiomers.