Imazalil is a chiral fungicide widely used to protect strawberries against gray mold, which may pose threats to food safety. This study aims to investigate the stereoselective behavior of imazalil during strawberry growth and strawberry wine production. A method was proposed and validated for the extraction and quantitative analysis of imazalil residues in strawberry, strawberry pomace, and strawberry wine by using ultra-high performance liquid chromatography-tandem mass spectrometry. The method exhibited mean recoveries ranging from 86.2% to 119.7% with relative standard deviations of 0.1-11.3%. The dissipation curve of imazalil during strawberry growth followed the first-order kinetic model with a half-life ranging from 6.5 to 7.1 days. Significant enantioselectivity of imazalil was observed in strawberry grown under field conditions and strawberry wine production process, with enantiomeric fraction values ranging from 0.51 (2 h) to 0.42 (27d) and from 0.48 (0d) to 0.52 (10d), respectively. ( + )-imazalil was preferentially degraded in strawberry...

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