Skip to main content
SpringerLink
Log in

Enantioselective Acute Toxicity and Bioactivity of Carfentrazone-ethyl enantiomers

  • Published:
Bulletin of Environmental Contamination and Toxicology Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Chai TT, Yang WW, Jing Q, Hou SC (2015) Direct enantioseparation of nitrogen-heterocyclic pesticides on cellulose-based chiral column by high-performance liquid chromatography. Chirality 27:32–38

    Article  CAS  Google Scholar 

  • Chen ZW, Wang J, Chen H, Wen YZ, Liu WP (2017) Enantioselective phytotoxicity of dichlorprop to arabidopsis thaliana: the effect of cytochrome P450 enzymes and the role of Fe. Environ Sci Technol 51:12007–12015

    Article  CAS  Google Scholar 

  • Dong MF, Ma YQ, Liu FM, Qian CF, Han LJ, Jiang SR (2009) Use of multiwalled carbon nanotubes as a SPE adsorbent for analysis of carfentrazone-ethyl in water. Chromatographia 69:73–77

    Article  CAS  Google Scholar 

  • Duan JS, Dong X, Shen Y, Gao BB, Zhang ZX, Gao TC, Wang MH (2018) Simultaneous determination of enantiomers of carfentrazone-ethyl and its metabolite in eight matrices using high-performance liquid chromatography-tandem mass spectrometry. J Sep Sci 41:3697–3705

    Article  CAS  Google Scholar 

  • Elmarakby SA, Supplee D, Cook R (2001) Degradation of [14C]carfentrazone-ethyl under aerobic aquatic conditions. J Agric Food Chem 49:5285–5293

    Article  CAS  Google Scholar 

  • Garrison AW (2006) Probing the enantioselectivity of chiral pesticides. Environ Sci Technol 40:16–23

    Article  Google Scholar 

  • http://sitem.herts.ac.uk/aeru/iupac/Reports/123.htm

  • Jing X, Yao GJ, Liu DH, Liu C, Wang F, Wang P, Zhou ZQ (2017) Exposure of frogs and tadpoles to chiral herbicide fenoxaprop-ethyl. Chemosphere 186:832

    Article  CAS  Google Scholar 

  • Koch M, Breithaupt C, Kiefersauer R, Freigang J, Huber R, Messerschmidt A (2004) Crystal structure of protoporphyrinogen IX oxidase: a key enzyme in haem and chlorophyll biosynthesis. EMBO J 23:1720–1728

    Article  CAS  Google Scholar 

  • Li YB, Dong FS, Liu XG, Xu J, Chen WY, Cheng L, Ning P, Li J, Wang YH, Zheng YQ (2010) Enantioselective separation of the carfentrazone-ethyl enantiomers in soil, water and wheat by HPLC. J Sep Sci 33:1973–1979

    Article  CAS  Google Scholar 

  • Li YB, Dong FS, Liu XG, Xu J, Chen X, Han YT, Liang XY, Zheng YQ (2013) Development of a multi-residue enantiomeric analysis method for 9 pesticides in soil and water by chiral liquid chromatography/tandem mass spectrometry. J Hazard Mater 250–251:9–18

    Article  Google Scholar 

  • Liu HJ, Cai WD, Huang RN, Xia HL, Wen YZ (2012) Enantioselective toxicity of metolachlor to scenedesmus obliquus in the presence of cyclodextrins. Chirality 24:181–187

    Article  CAS  Google Scholar 

  • Moser H, Vogel C (1991) Optically active N-(1′-methyl-2′-methoxyethyl)-N-chloroacetyl–2-ethyl-6-methylaniline as herbicide US5002606

  • OECD (2006) Organization for economic cooperation and development guidelines for the testing of chemicals. Freshwater Alga and Cyanobacteria, Growth Inhibition Test

  • Organization for Economic Cooperation and Development (OECD) (1995) Report of the final ring test of the Daphnia magna reproduction study

  • Organization for Economic Cooperation and Development (OECD) (2013) Guideline for fish embryo acute toxicity (FET) test

  • Qi YL, Liu DH, Liu C, Liang YR, Zhan J, Zhou ZQ, Wang P (2017) Enantioselective behaviour of the herbicide fluazifop-butyl in vegetables and soil. Food Chem 221:1120–1127

    Article  CAS  Google Scholar 

  • Qu H, Ma RX, Liu DH, Gao J, Wang F, Zhou ZQ, Wang P (2016) Environmental behavior of the chiral insecticide fipronil: Enantioselective toxicity, distribution and transformation in aquatic ecosystem. Water Res 105:138–146

    Article  CAS  Google Scholar 

  • Tian MM, Zhang Q, Hua XD, Tang BW, Gao BB, Wang MH (2016) Systemic stereoselectivity study of flufiprole: stereoselective bioactivity, acute toxicity and environmental fate. J Hazard Mater 320:487–494

    Article  CAS  Google Scholar 

  • Wang P, Jiang SR, Liu DH, Jia GF, Wang QX, Wang P, Zhou ZQ (2005) Effect of alcohols and temperature on the direct chiral resolutions of fipronil, isocarbophos and carfentrazone-ethyl. Biomed Chromatogr 19:454–458

    Article  CAS  Google Scholar 

  • Xie F, Liu HJ, Cai WD (2010) Enantioselectivity of racemic metolachlor and S-metolachlor in maize seedlings. J Environ Sci Health B 45:774–782

    Article  CAS  Google Scholar 

  • Yang WW, Qiu J, Chen TJ, Yang SM, Hou SC (2012) Direct enantioseparation of nitrogen-heterocyclic pesticides on amylose-tris-(5-chloro-2- methylphenylcarbamate) by reversed-phase high-performance liquid chromatography. Chirality 24:1031–1036

    Article  CAS  Google Scholar 

  • Zhang Q, Hua XD, Shi HY, Liu JS, Tian MM, Wang MH (2015) Enantioselective bioactivity, acute toxicity and dissipation in vegetables of the chiral triazole fungicide flutriafol. J Hazard Mater 284:65–72

    Article  CAS  Google Scholar 

Download references

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).

Author information

Authors and Affiliations

  1. Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, Nanjing, 210095, People’s Republic of China

    Jinsheng Duan, Beibei Gao, Zhaoxian Zhang & Minghua Wang

  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 Agriculture, Hefei, 230031, People’s Republic of China

    Jinsheng Duan, Mingna Sun, Yang Shen & Tongchun Gao

Authors
  1. Jinsheng Duan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mingna Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yang Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Beibei Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhaoxian Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tongchun Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Minghua Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Minghua Wang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 375 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Duan, J., Sun, M., Shen, Y. et al. Enantioselective Acute Toxicity and Bioactivity of Carfentrazone-ethyl enantiomers. Bull Environ Contam Toxicol 101, 651–656 (2018). https://doi.org/10.1007/s00128-018-2474-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00128-018-2474-6

Keywords

Search

Navigation