title: Chiral quizalofop-ethyl and its metabolite quizalofop-acid in soils: Enantioselective degradation, enzymes interaction and toxicity to Eisenia foetida.
abstract: An enantioselective chromatographic method to analyze enantiomers of quizalofop-ethyl and its metabolite quizalofop-acid was established using a high-performance liquid chromatography (HPLC) on (R, R) Whelk-O 1 column. The enantioselective degradation kinetics of quizalofop-ethyl and quizalofop-acid in three soils were investigated. Moreover, the interaction with urease and catalase in the soils and the acute toxicity to Eisenia foetida of quizalofop-ethyl were also determined in order to assess their metabolism mechanism and environmental risk. From the results, quizalofop-ethyl was configurationally stable and was hydrolyzed rapidly to quizalofop-acid, which also degraded enantioselectively but slowly, and the inversion of the S-(-)-quizalofop-acid into the R-(+)-quizalofop-acid was observed in Xinxiang soil. In addition, quizalofop-ethyl and quizalofop-acid enantioselectively affected urease activity but not catalase. The acute toxicity assays to earthworm indicated that the racemic quizalofop-ethyl and quizalofop-acid were more toxic than quizalofop-p-ethyl and quizalofop-p-acid respectively, dramatically, the toxicity of the metabolite was much higher than the parent compound. These results revealed the enantioselective degradation of quizalofop-ethyl and quizalofop-acid, and the differences of toxicity among the enantiomers of the parent compound and the metabolite, which should be considered in future environmental risk evaluation.
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Beijing, 100193, PR China.
authors.forename: Lin
authors.initials: L
authors.lastname: Ma
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Beijing, 100193, PR China.
authors.forename: Hui
authors.initials: H
authors.lastname: Liu
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Beijing, 100193, PR China.
authors.forename: Han
authors.initials: H
authors.lastname: Qu
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Beijing, 100193, PR China; Chinese People's Armed Police Force Academy, Langfang, 065000, PR China.
authors.forename: Yangguang
authors.initials: Y
authors.lastname: Xu
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, 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, Beijing, 100193, PR China.
authors.forename: Mingjing
authors.initials: M
authors.lastname: Sun
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Beijing, 100193, PR China.
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Zhou
authors.affiliation: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Beijing, 100193, PR China. Electronic address: liudh@cau.edu.cn.
authors.forename: Donghui
authors.initials: D
authors.lastname: Liu
mesh_terms: D000818:Animals; D001673:Biodegradation, Environmental; D002374:Catalase / Q000032:analysis; D002851:Chromatography, High Pressure Liquid; D007700:Kinetics; D009835:Oligochaeta / Q000187:drug effects*; D011422:Propionates / Q000737:chemistry / Q000633:toxicity*; D011810:Quinoxalines / Q000737:chemistry / Q000633:toxicity*; D012987:Soil / Q000737:chemistry*; D012989:Soil Pollutants / Q000032:analysis / Q000737:chemistry / Q000633:toxicity*; D013237:Stereoisomerism; D014510:Urease / Q000032:analysis
chemical_list: D011422:Propionates; D011810:Quinoxalines; D012987:Soil; D012989:Soil Pollutants; C477202:quizalofop; C064835:quizalofop-ethyl; D002374:Catalase; D014510:Urease
keywords: Earthworm; Enantioselective; Environmental behavior; Quizalofop; Soil