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Environmental behavior of the chiral fungicide epoxiconazole in earthworm-soil system: Enantioselective enrichment, degradation kinetics, chiral metabolite identification, and biotransformation mechanism
Environment International ( IF 11.8 ) Pub Date : 2022-07-30 , DOI: 10.1016/j.envint.2022.107442
Pengfei Xue 1 , Xiaowei Liu 1 , Hao Jia 1 , Haiyue Yuan 1 , Bingjie Liu 2 , Jingran Zhang 2 , Zeying He 1
Affiliation  

The environmental impact of the chiral fungicide epoxiconazole and its chiral transformation products (TPs) on non-target organisms and the environment has become a significant concern due to its widespread use in agricultural practice. Enantioselectivity studies of parent contaminants cannot adequately assess the complexity of its chiral TPs in the environment. This study aimed to investigate the environmental behavior of epoxiconazole in an earthworm-soil system. 2S,3R-(–)-epoxiconazole was preferentially enriched in earthworms during the accumulation phase (p < 0.05), but no enantioselectivity was observed during the elimination phase. One methoxylated and four hydroxylated chiral TPs were identified in soil, earthworm, and excrement. The epoxy ring hydroxylated TP and methoxylated TP of epoxiconazole were discovered for the first time in the environment. The chemically specific enantioselectivity with enantiomer fraction (EF) > 0.8 was observed for the TPs in different matrices. The CYP450 monooxygenase of earthworm was significant activated. In vitro enzyme metabolism experiments (earthworm microsomes and recombinant CYP450 enzymes CYP2A6, CYP 2C9, and CYP 3A4) were carried out to further explain the biotransformation mechanism of epoxiconazole in earthworm. This study provides new evidence of enantiomeric biotransformation of chiral fungicide epoxiconazole in the earthworm-soil system and could provide valuable insights into their environmental risk assessment.



中文翻译:

手性杀菌剂氧唑菌在蚯蚓-土壤系统中的环境行为:对映选择性富集、降解动力学、手性代谢物鉴定和生物转化机制

手性杀菌剂氧唑菌及其手性转化产物(TPs)对非靶标生物和环境的影响由于其在农业实践中的广泛应用而成为一个重要的问题。母体污染物的对映选择性研究无法充分评估其手性 TP 在环境中的复杂性。本研究旨在调查氧唑菌在蚯蚓-土壤系统中的环境行为。2S,3R-(-)-氧唑菌在积累阶段优先富集于蚯蚓体内(p < 0.05),但在消除阶段没有观察到对映选择性。在土壤、蚯蚓和粪便中鉴定出一种甲氧基化和四种羟基化手性 TP。环氧环羟基化TP和氧环唑的甲氧基化TP在环境中首次被发现。对于不同基质中的 TP,观察到对映异构体分数 (EF) > 0.8 的化学特异性对映选择性。蚯蚓的CYP450单加氧酶被显着激活。体外_进行了酶代谢实验(蚯蚓微粒体和重组CYP450酶CYP2A6、CYP 2C9和CYP 3A4),以进一步解释氧唑菌在蚯蚓体内的生物转化机制。这项研究为蚯蚓-土壤系统中手性杀菌剂氧唑菌的对映体生物转化提供了新的证据,并可以为其环境风险评估提供有价值的见解。

更新日期:2022-07-31
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