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Stereoselective absorption,elimination,and transformation of chiral fungicide difenoconazole in an earthworm-soil system
Received:March 08, 2024  
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KeyWord:difenoconazole;enantioselectivity;bioaccumulation;transformation product;degradation pathway
Author NameAffiliationE-mail
WANG Jiafu Key Laboratory for Environmental Factors Control of Agro-product Quality Safety, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China
Agro-Environmental Protection Institute, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China 
 
FU Jiqiang Key Laboratory for Environmental Factors Control of Agro-product Quality Safety, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China
Agro-Environmental Protection Institute, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China 
 
WANG Jishi Key Laboratory for Environmental Factors Control of Agro-product Quality Safety, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China
Agro-Environmental Protection Institute, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China 
 
ZHANG Yanwei Key Laboratory for Environmental Factors Control of Agro-product Quality Safety, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China
Agro-Environmental Protection Institute, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China 
 
GENG Yue Key Laboratory for Environmental Factors Control of Agro-product Quality Safety, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China
Agro-Environmental Protection Institute, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China 
 
HE Zeying Key Laboratory for Environmental Factors Control of Agro-product Quality Safety, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China
Agro-Environmental Protection Institute, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China 
hezeying@caas.cn 
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Abstract:
      This study was conducted to comprehensively explore the enantioselective environmental behavior of the triazole fungicide difenoconazole in the earthworm-soil system. Laboratory experiments were performed to study the bioaccumulation, elimination, and degradation pathways of chiral difenoconazole. Four stereoisomers of difenoconazole were separated and determined by SFC-MS/MS. Significant enantioselectivity was observed during the accumulation phase, and(2R, 4R)-difenoconazole and(2R, 4S)-difenoconazole were preferentially accumulated in earthworms. Five transformation products(TPs)were identified by UHPLC-QTOF/MS, namely 3- chloro, 4-hydroxy difenoconazole, CGA-205374, CGA-205375, 3-chloro, 4-hydroxy CGA-205375, and CGA-71019(1, 2, 4-triazole). The main transformation pathways observed for difenoconazole in earthworms and soil were hydrolysis and hydroxylation. Furthermore, the chiral transformation product, 3-chloro, 4-hydroxy difenoconazole, was generated with significant enantioselectivity.