title: Enantioselective degradation and chiral stability of the herbicide fluazifop-butyl in soil and water.
abstract: The stereoselective degradation and transformation of the enantiomers of the herbicide fluazifop-butyl in soil and water were studied to investigate the environmental behavior and chiral stability of the optical pure product. Its main chiral metabolite fluazifop was also monitored. LC/MS/MS with Chiralpak IC chiral column was used to separate the enantiomers of fluazifop-butyl and fluazifop. Validated enantioselective residue analysis methods were established with recoveries ranging from 77.1 to 115.4% and RSDs from 0.85 to 8.9% for the enantiomers. It was found the dissipation of fluazifop-butyl was rapid in the three studied soils (Beijing, Harbin and Anhui soil), and the degradation half-lives of the enantiomers ranged from 0.136 to 2.7 d. Enantioselective degradations were found in two soils. In Beijing soil, R-fluazifop-butyl was preferentially degraded leading to relative enrichment of S-enantiomer, but in Anhui soil, S-fluazifop-butyl dissipated faster. There was no conversion of the R-fluazifop-butyl into S-fluazifop-butyl or vice versa in the soils. The formation of fluazifop in the soils was rapidly accompanied with the fast degradation of fluazifop-butyl, and the enantioselectivity and the transformation of S-fluazifop to R-fluazifop were found. The degradation of fluazifop-butyl in water was also quick, with half-lives of the enantiomers ranging from 0.34 to 2.52 d, and there was no significant enantioselectivity of the degradation of fluazifop-butyl and the formation of fluazifop. The effects of pH on the degradation showed fluazifop-butyl enantiomers degraded faster in alkaline conditions. This study showed an evidence of enantioselective behavior and enantiomerization of the chiral herbicide fluazifop-butyl.
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan road No.2, Beijing, 100193, PR China.
authors.forename: Yanli
authors.initials: Y
authors.lastname: Qi
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan road No.2, Beijing, 100193, PR China.
authors.forename: Donghui
authors.initials: D
authors.lastname: Liu
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan road No.2, Beijing, 100193, PR China.
authors.forename: Mai
authors.initials: M
authors.lastname: Luo
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan road No.2, Beijing, 100193, PR China.
authors.forename: Xu
authors.initials: X
authors.lastname: Jing
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan road No.2, Beijing, 100193, PR China.
authors.forename: Peng
authors.initials: P
authors.lastname: Wang
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan road No.2, Beijing, 100193, PR China. Electronic address: zqzhou@cau.edu.cn.
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Zhou
mesh_terms: D001419:Bacteria / Q000378:metabolism; D004784:Environmental Monitoring / Q000379:methods*; D006540:Herbicides / Q000737:chemistry / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D011725:Pyridines / Q000737:chemistry / Q000378:metabolism*; D012989:Soil Pollutants / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D014874:Water Pollutants, Chemical / Q000737:chemistry / Q000378:metabolism*
chemical_list: D006540:Herbicides; D011725:Pyridines; D012989:Soil Pollutants; D014874:Water Pollutants, Chemical; C050585:fluazifop-butyl
keywords: Enantiomerization; Enantioselective degradation; Fluazifop-butyl; Metabolite