TY - JOUR
T1 - Chiral quizalofop-ethyl and its metabolite quizalofop-acid in soils
T2 - Enantioselective degradation, enzymes interaction and toxicity to Eisenia foetida
AU - Ma, Lin
AU - Liu, Hui
AU - Qu, Han
AU - Xu, Yangguang
AU - Wang, Peng
AU - Sun, Mingjing
AU - Zhou, Zhiqiang
AU - Liu, Donghui
N1 - Publisher Copyright:
© 2016 Elsevier Ltd.
PY - 2016/6/1
Y1 - 2016/6/1
N2 - 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.
AB - 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.
KW - Earthworm
KW - Enantioselective
KW - Environmental behavior
KW - Quizalofop
KW - Soil
UR - http://www.scopus.com/inward/record.url?scp=84960080846&partnerID=8YFLogxK
U2 - 10.1016/j.chemosphere.2016.02.084
DO - 10.1016/j.chemosphere.2016.02.084
M3 - Article
C2 - 26971169
AN - SCOPUS:84960080846
SN - 0045-6535
VL - 152
SP - 173
EP - 180
JO - Chemosphere
JF - Chemosphere
ER -