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Systemic stereoselectivity study of flufiprole: Stereoselective bioactivity, acute toxicity and environmental fate.
- Source :
-
Journal of Hazardous Materials . Dec2016, Vol. 320, p487-494. 8p. - Publication Year :
- 2016
-
Abstract
- In this study, the stereoselectivity of flufiprole enantiomers in regards to their bioactivity, acute toxicity and environmental fate is reported for the first time. Four types of representative insects ( Plutella xylostella , Nilaparvata lugens , Mythimna separata and Acyrthosiphon pisum ) were used to investigate enantioselective bioactivity. Acute toxicities of flufiprole enantiomers toward two non-target organisms were also evaluated. Moreover, stereoselective degradation in four vegetables under field conditions was studied in response to food safety concerns. The bioactivity of ( R )-flufiprole was 1.9–5.1 times higher than that of ( S )-flufiprole. ( R )-flufiprole also showed 3.7–5.7 times higher acute toxicity to Scenedesmus obliquus and Trichogramma japonicum Ashmead than ( S )-flufiprole. Opposite stereoselective degradation of the two enantiomers was observed in pak choi, spinach cucumber, and tomato. ( S )-flufiprole degraded faster in pak choi and spinach, resulting in an enrichment of ( R )-isomer. By contrast, ( R )-isomer was preferentially degraded in cucumber and tomato. Molecular simulation technology was used to illuminate the mechanism of enantioselective bioactivity. The Glide Score (−5.82 kcal/mol) for ( R )-isomer was better than that (−5.11 kcal/mol) of ( S )-isomer and this calculation showed ( R )-flufiprole was more effective in pest control. Consequently, significant stereoselectivity of flufiprole enantiomers should be taken into account when assessing the environmental health risk of the pesticide. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 03043894
- Volume :
- 320
- Database :
- Academic Search Index
- Journal :
- Journal of Hazardous Materials
- Publication Type :
- Academic Journal
- Accession number :
- 118401576
- Full Text :
- https://doi.org/10.1016/j.jhazmat.2016.08.045