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Enantioselective Acute Toxicity and Bioactivity of Carfentrazone-ethyl enantiomers

  • Jinsheng Duan
  • Mingna Sun
  • Yang Shen
  • Beibei Gao
  • Zhaoxian Zhang
  • Tongchun Gao
  • Minghua WangEmail author
Article

Abstract

The stereoselective herbicidal bioactivity and toxicity toward aquatic organisms of carfentrazone-ethyl enantiomers were investigated. The results showed that there was significant enantioselective acute toxicity toward Selenastrum bibraianum. In addition, S-(−)-carfentrazone-ethyl was 4.8 times more potent than R-(+)-isomer. However, a slight enantioselectivity was observed for Daphnia magna and Danio rerio. The stereoselective herbicidal bioactivity of carfentrazone-ethyl enantiomers was observed by assessing maize root-length inhibition. The results clarified that S-(−)-carfentrazone-ethyl (EC50 1.94 mg/L) > Rac-carfentrazone-ethyl (EC50 2.18 mg/L) > R-(+)-carfentrazone-ethyl (EC50 3.96 mg/L). The herbicidal bioactivity of S-(−)-carfentrazone-ethyl was 2 times higher more than R-(+)-isomer. The mechanism of enantioselective bioactivity was illustrated using molecular simulation software. The GlideScore energies of S-(−)-carfentrazone-ethyl and R-(+)-carfentrazone-ethyl were − 6.15 kcal/mol and − 5.59 kcal/mol, indicating that the S-form has a greater affinity to the active site of protoporphyrinogen oxidase, which is consistent with the results of the bioactive assay. This study can rise the significance of risk assessments for carfentrazone-ethyl herbicide.

Keywords

Carfentrazone-ethyl Chiral pesticides Acute toxicity Bioactivity Molecular simulation 

Notes

Acknowledgements

This work was supported by the National Key Research and Development Program of China (Grant No. 2016YFD0200207) and the Project of Science and Technology innovation team from the Anhui Academy of Agricultural Sciences (Grant No. 14C1105).

Supplementary material

128_2018_2474_MOESM1_ESM.docx (376 kb)
Supplementary material 1 (DOCX 375 KB)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Pesticide Science, College of Plant ProtectionNanjing Agricultural UniversityNanjingPeople’s Republic of China
  2. 2.Institute of Plant Protection and Agro-Product Safety, Anhui Academy of Agricultural Sciences, Key Laboratory of Agro-Product Safety Risk Evaluation (Hefei)Ministry of AgricultureHefeiPeople’s Republic of China

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