AbstractThe enantioselective degradation of tebuconazole has been investigated to elucidate the behaviors in agricultural soils, cabbage, and cucumber fruit. Rac‐tebuconazole was fortified into three types of agricultural soils and sprayed foliage of cabbage and cucumber, respectively. The degradation kinetics, enantiomer fraction and enantiomeric selectivity were determined by reverse‐phase high‐performance liquid chromatography (HPLC) and liquid chromatography‐mass spectrometry/mass spectrometry (LC‐MS/MS) on a Lux amylose‐2 chiral column. The process of the degradation of tebuconazole enantiomers followed first‐order kinetic in the test soils and vegetables. It has been shown that the degradation of tebuconazole was enantioselective. The results indicated that the (+)‐S‐tebuconazole showed a faster degradation in cabbage, while the (−)‐R‐tebuconazole dissipated faster than (+)‐S‐form in cucumber fruit and the test soils. Chirality, 2012. © 2011 Wiley Periodicals, Inc.