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Systemic Stereoselectivity Study of Etoxazole: Stereoselective Bioactivity, Acute Toxicity, and Environmental Behavior in Fruits and Soils.
J Agric Food Chem. 2019 Jun 19; 67(24):6708-6715.JA

Abstract

This is the first systemic assessment of the stereoselectivity of etoxazole enantiomers. Etoxazole's stereoselective bioactivity was assessed against target organisms (Tetranychus urticae eggs and Tetranychus cinnabarinus eggs), and its acute toxicity was assessed toward nontarget aquatic organisms (Daphnia magna and Danio rerio). Additionally, stereoselective elimination was investigated in three species of fruits (grape and strawberry grown in a greenhouse and apple grown in an open field) and in field soil. The ovicidal activity of (+)-(S)-etoxazole against Tetranychus urticae and Tetranychus cinnabarinus eggs was about 16 and 24 times higher, respectively, than that of (-)-(R)-etoxazole. Inconsistent order of etoxazole isomer toxicity was found toward different aquatic organisms: (+)-(S)-etoxazole showed nearly 8.7 times higher acute toxicity than (-)-(R)-etoxazole toward Daphnia magna, whereas (-)-(R)-etoxazole was ∼4.5 times more toxic to Danio rerio than (+)-(S)-etoxazole. Stereoselective degradation of etoxazole enantiomers showed significant variation in various fruits and field soil. The (+)-(S)-etoxazole was preferentially dissipated in grape and strawberry fruits grown under greenhouse condition, whereas (-)-(R)-etoxazole degraded faster than its antipode in apple fruits and soils under open-field condition. Overall, the stereoselectivity of etoxazole enantiomers should be fully considered in comprehensive environmental health risk in future work.

Authors+Show Affiliations

Ministry of Agriculture and Rural Affairs , Institute of Pomology, Chinese Academy of Agricultural Sciences/Laboratory of Quality & Safety Risk Assessment for Fruit , Xingcheng 125100 , P. R. China.Ministry of Agriculture and Rural Affairs , Institute of Pomology, Chinese Academy of Agricultural Sciences/Laboratory of Quality & Safety Risk Assessment for Fruit , Xingcheng 125100 , P. R. China.Ministry of Agriculture and Rural Affairs , Institute of Pomology, Chinese Academy of Agricultural Sciences/Laboratory of Quality & Safety Risk Assessment for Fruit , Xingcheng 125100 , P. R. China.Ministry of Agriculture and Rural Affairs , Institute of Pomology, Chinese Academy of Agricultural Sciences/Laboratory of Quality & Safety Risk Assessment for Fruit , Xingcheng 125100 , P. R. China.Ministry of Agriculture and Rural Affairs , Institute of Pomology, Chinese Academy of Agricultural Sciences/Laboratory of Quality & Safety Risk Assessment for Fruit , Xingcheng 125100 , P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31140799

Citation

Chang, Weixia, et al. "Systemic Stereoselectivity Study of Etoxazole: Stereoselective Bioactivity, Acute Toxicity, and Environmental Behavior in Fruits and Soils." Journal of Agricultural and Food Chemistry, vol. 67, no. 24, 2019, pp. 6708-6715.
Chang W, Nie J, Yan Z, et al. Systemic Stereoselectivity Study of Etoxazole: Stereoselective Bioactivity, Acute Toxicity, and Environmental Behavior in Fruits and Soils. J Agric Food Chem. 2019;67(24):6708-6715.
Chang, W., Nie, J., Yan, Z., Wang, Y., & Farooq, S. (2019). Systemic Stereoselectivity Study of Etoxazole: Stereoselective Bioactivity, Acute Toxicity, and Environmental Behavior in Fruits and Soils. Journal of Agricultural and Food Chemistry, 67(24), 6708-6715. https://doi.org/10.1021/acs.jafc.9b01257
Chang W, et al. Systemic Stereoselectivity Study of Etoxazole: Stereoselective Bioactivity, Acute Toxicity, and Environmental Behavior in Fruits and Soils. J Agric Food Chem. 2019 Jun 19;67(24):6708-6715. PubMed PMID: 31140799.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Systemic Stereoselectivity Study of Etoxazole: Stereoselective Bioactivity, Acute Toxicity, and Environmental Behavior in Fruits and Soils. AU - Chang,Weixia, AU - Nie,Jiyun, AU - Yan,Zhen, AU - Wang,Yujiao, AU - Farooq,Saqib, Y1 - 2019/06/05/ PY - 2019/5/30/pubmed PY - 2019/7/19/medline PY - 2019/5/30/entrez KW - acute toxicity KW - bioactivity KW - environmental behavior KW - etoxazole enantiomer SP - 6708 EP - 6715 JF - Journal of agricultural and food chemistry JO - J. Agric. Food Chem. VL - 67 IS - 24 N2 - This is the first systemic assessment of the stereoselectivity of etoxazole enantiomers. Etoxazole's stereoselective bioactivity was assessed against target organisms (Tetranychus urticae eggs and Tetranychus cinnabarinus eggs), and its acute toxicity was assessed toward nontarget aquatic organisms (Daphnia magna and Danio rerio). Additionally, stereoselective elimination was investigated in three species of fruits (grape and strawberry grown in a greenhouse and apple grown in an open field) and in field soil. The ovicidal activity of (+)-(S)-etoxazole against Tetranychus urticae and Tetranychus cinnabarinus eggs was about 16 and 24 times higher, respectively, than that of (-)-(R)-etoxazole. Inconsistent order of etoxazole isomer toxicity was found toward different aquatic organisms: (+)-(S)-etoxazole showed nearly 8.7 times higher acute toxicity than (-)-(R)-etoxazole toward Daphnia magna, whereas (-)-(R)-etoxazole was ∼4.5 times more toxic to Danio rerio than (+)-(S)-etoxazole. Stereoselective degradation of etoxazole enantiomers showed significant variation in various fruits and field soil. The (+)-(S)-etoxazole was preferentially dissipated in grape and strawberry fruits grown under greenhouse condition, whereas (-)-(R)-etoxazole degraded faster than its antipode in apple fruits and soils under open-field condition. Overall, the stereoselectivity of etoxazole enantiomers should be fully considered in comprehensive environmental health risk in future work. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/31140799/Systemic_Stereoselectivity_Study_of_Etoxazole:_Stereoselective_Bioactivity_Acute_Toxicity_and_Environmental_Behavior_in_Fruits_and_Soils_ L2 - https://dx.doi.org/10.1021/acs.jafc.9b01257 DB - PRIME DP - Unbound Medicine ER -