Skip to main content

Stereoselective degradation of flutriafol and tebuconazole in grape

Environmental Science and Pollution Research volume 22, pages 4350–4358 (2015)Cite this article

Abstract

The stereoselective dissipation of flutriafol and tebuconazole in grape had been studied. A simple and sensitive method for determination of flutriafol and tebuconazole enantiomers in grape was developed by high-performance liquid chromatography on a cellulose tris(3-chloro-4-methylphenylcarbamate) column. The limits of quantification for flutriafol and tebuconazole in grape were 0.033 and 0.043 mg kg−1, respectively. The dissipations of flutriafol and tebuconazole stereoisomers in grape followed first-order kinetics (R 2 > 0.93). The stereoisomers of flutriafol and tebuconazole were enantioselectively degraded in grape, and tebuconazole was more enantioselective than flutriafol. The half-life of (−)-tebuconazole was 5.2 days and shorter than (+)-tebuconazole with half-life of 6.4 days. The (−)-flutriafol was also preferentially degraded in grape, the half-lives of which were 6.59 and 6.98 days for (−) and (+)-flutriafol, respectively. The enantiomeric ratio value of the two fungicides was nearly 1.0 at the 1st day and increased to 1.143 for flutriafol and 2.015 for tebuconazole at the 28th day. The stereoselective dissipations could provide a reference to fully evaluate the risks of two important chiral triazole fungicides.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

Fig. 1
Fig. 2
Fig. 3

References

  • Buerge IJ, Poiger T, Mller MD, Buser H (2003) Enantioselective degradation of metalaxyl in soils: chiral preference changes with soil pH. Environ Sci Technol 37:2668–2674

    Article  CAS  Google Scholar 

  • Buser H, Muller MD, Poiger T, Balmer ME (2002) Environmental behavior of the chiral acetamide pesticide metalaxyl: enantioselective degradation and chiral stability in soil. Environ Sci Technol 36:221–226

    Article  CAS  Google Scholar 

  • Cao X, Hu M, Zhang J, Li F, Yang Y, Liu D, Liu SH (2009) Determination of stereoselective interaction between enantiomers of chiral γ-aryl-1 H-1, 2, 4-triazole derivatives and Penicillium digitatum. J Agric Food Chem 57:6914–6919

    Article  CAS  Google Scholar 

  • Chang M, Kim TH, Kim H (2008) Stereoselective synthesis of (+)-flutriafol. Tetrahedron 19:1504–1508

    Article  CAS  Google Scholar 

  • De Liguoro M, Dalla Bona M, Gallina G, Capolongo F, Gallocchio F, Binato G, Di Leva V (2014) A monitoring of chemical contaminants in waters used for field irrigation and livestock watering in the Veneto region (Italy), using bioassays as a screening tool. Environ Sci Pollut Res 21:3546–3557

    Article  CAS  Google Scholar 

  • Diao JL, Xu P, Wang P, Lu D, Lu Y, Zhou ZQ (2010) Enantioselective degradation in sediment and aquatic toxicity to Daphnia magna of the herbicide lactofen enantiomers. J Agric Food Chem 58:2439–2445

    Article  CAS  Google Scholar 

  • Kabashima T, Yu Z, Tang C, Nakagawa Y, Okumura K, Shibata T, Lu J, Kai M (2009) A selective fluorescence reaction for peptides and chromatographic analysis. Peptides 29:356–363

    Article  Google Scholar 

  • Li J, Dong FS, Xu J, Liu X, Li YB, Shan W, Zheng YQ (2011) Enantioselective determination of triazole fungicide simeconazole in vegetables, fruits, and cereals using modified QuEChERS (quick, easy, cheap, effective, rugged and safe) coupled to gas chromatography/tandem mass spectrometry. Anal Chim Acta 702:127–135

    Article  CAS  Google Scholar 

  • Li Y, Dong FS, Liu X, Xu J, Li J, Kong Z, Chen X, Zheng YQ (2012) Enantioselective determination of triazole fungicide tebuconazole in vegetables, fruits, soil and water by chiral liquid chromatography-tandem mass spectrometry. J Sep Sci 35:206–215

    Article  CAS  Google Scholar 

  • Liang H, Qiu J, Li L, Li W, Zhou ZQ, Liu F, Qiu L (2012) Stereoselective dissipation of epoxiconazole in grape (Vitis vinifera cv. Kyoho) and soil under field conditions. Chemosphere 87:982–987

    Article  CAS  Google Scholar 

  • Liu WP, Gan J, Schlenk D, Jury WA (2005) Enantioselectivity in environmental safety of current chiral insecticides. Proc Natl Acad Sci U S A 102:701–706

    Article  CAS  Google Scholar 

  • Navarro S, Vela N, Perez G, Navarro G (2011) Effect of sterol biosynthesis-inhibiting (SBI) fungicides on the fermentation rate and quality of young ale beer. Food Chem 126:623–629

    Article  CAS  Google Scholar 

  • Schenck FJ, Lehotay SJ (2000) Does further clean-up reduce the matrix enhancement effect in gas chromatographic analysis of pesticide residues in food. J Chromatogr A 868:51–61

    Article  CAS  Google Scholar 

  • Shen Z, Zhang P, Xu X, Wang X, Zhou Z, Liu D (2011) Gender-related differences in stereoselective degradation of flutriafol in rabbits. J Agric Food Chem 59:10071–10077

    Article  CAS  Google Scholar 

  • Stehmann C, Waard D, Maarten A (1996) Sensitivity of populations of Botrytis cinerea to triazoles, benomyl and vinclozolin. Eur J Plant Pathol 102:171–180

    Article  CAS  Google Scholar 

  • Ulrich EM, Helsel DR, Foreman WT (2003) Complications with using ratios for environmental data: comparing enantiomeric ratios (ERs) and enantiomer fractions (EFs). Chemosphere 53:531–538

    Article  CAS  Google Scholar 

  • Wang P, Jiang S, Liu D, Wang P, Zhou ZQ (2005) Direct enantiomeric resolutions of chiral triazole pesticides by high-performance liquid chromatography. J Biochem Biophys Methods 62:219–230

    Article  CAS  Google Scholar 

  • Wang X, Jia G, Qiu J, Diao J, Zhu W, Lu C, Zhou ZQ (2007) Stereoselective degradation of fungicide benalaxyl in soils and cucumber plants. Chirality 19:300–306

    Article  Google Scholar 

  • Wang XQ, Zhang H, Wu C, Wang X, Xu H, Wang XY, Li Z (2012) Enantioselective degradation of tebuconazole in cabbage, cucumber, and soils. Chirality 24:104–111

    Article  Google Scholar 

  • Wang M, Zhang Q, Cong LJ, Yin W, Wang MH (2014) Enantioselective degradation of metalaxyl in cucumber, cabbage, spinach and pakchoi. Chemosphere 95:241–246

    Article  CAS  Google Scholar 

  • Yang L, Li Z, Li Y (2002) Bioactivity investigation of triazole fungicide enantiomers. Chin J Pestic Sci 4:67–70

    CAS  Google Scholar 

  • Ye J, Wu J, Liu WP (2009) Enantioselective separation and analysis of chiral pesticides by high-performance liquid chromatography. TrAC Trends Anal Chem 28:1148–1163

    Article  CAS  Google Scholar 

  • Ye J, Zhao M, Liu J, Liu WP (2010) Enantioselectivity in environmental risk assessment of modern chiral pesticides. Environ Pollut 158:2371–2383

    Article  CAS  Google Scholar 

  • Zhang H, Wang XQ, Qian M, Wang X, Xu H, Xu M, Wang Q (2011) Residue analysis and degradation studies of fenbuconazole and myclobutanil in strawberry by chiral high-performance liquid chromatography-tandem mass spectrometry. J Agric Food Chem 59:12012–12017

    Article  CAS  Google Scholar 

  • Zhang H, Qian M, Wang XQ, Wang X, Xu H, Qi P, Wang Q, Wang MH (2012) Analysis of tebuconazole and tetraconazole enantiomers by chiral HPLC-MS/MS and application to measure enantioselective degradation in strawberries. Food Anal Methods 5:1342–1348

    Article  Google Scholar 

  • Zhang Q, Tian MM, Wang MY, Shi HY, Wang MH (2014) Simultaneous enantioselective determination of triazole fungicide Flutriafol in vegetables, fruits, wheat, soil and water by reversed-phase high-performance liquid chromatography. J Agric Food Chem 62:2809–2815

    Article  CAS  Google Scholar 

  • Zhou Y, Ling L, Kunde L, Zhang XPZ, Liu WP (2009) Enantiomer separation of triazole fungicides by high-performance liquid chromatography. Chirality 21:421–427

    Article  CAS  Google Scholar 

  • Zhu W, Qiu J, Dang Z, Lu C, Jia G, Li L, Zhou ZQ (2007) Stereoselective degradation kinetics of tebuconazole in rabbits. Chirality 19:141–147

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Special Fund for Agro-scientific Research in the Public Interest (201203022) and the National “863” High-Tech Research Program of China (2011AA100806).

Author information

Authors and Affiliations

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

    Qing Zhang, Xiude Hua, Yu Yang, Wei Yin, Mingming Tian, Haiyan Shi & Minghua Wang

  2. State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing, 210095, People’s Republic of China

    Qing Zhang, Xiude Hua, Yu Yang, Wei Yin, Mingming Tian, Haiyan Shi & Minghua Wang

Authors
  1. Qing Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xiude Hua
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wei Yin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mingming Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Haiyan Shi
    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.

Additional information

Qing Zhang and Xiude Hua contributed equally to this paper.

Responsible editor: Ester Heath

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Zhang, Q., Hua, X., Yang, Y. et al. Stereoselective degradation of flutriafol and tebuconazole in grape. Environ Sci Pollut Res 22, 4350–4358 (2015). https://doi.org/10.1007/s11356-014-3673-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-014-3673-2

Keywords

  • Flutriafol
  • Tebuconazole
  • Enantiomers
  • Chirality
  • Stereoselective dissipation
  • Grape