Skip to main content

Enantioselective Behavior of Chiral Difenoconazole in Apple and Field Soil

Abstract

Difenoconazole is a universal chiral fungicide which is widely used in apples. Recently, it is still employed as racemic mixtures without distinction of the enantiomers, which may lead to an incomplete risk assessment. Here, we analyzed the stereoselective degradation of difenoconazole in apple fruits and open-field soil using an HPLC–UV system. Different trends were established in various apple varieties under identical environmental conditions. No significant differences were found in its enantioselectivity of the degradation processes applied in the field soil of an apple orchard. However, preferential dissipation of (2R,4R)-difenoconazole and (2R,4S)-difenoconazole was observed in Hanfu and Fuji apples, resulting in the enrichment of stereoisomers of (2S,4S)-difenoconazole and (2S,4R)-difenoconazole. Meanwhile, no significant enantioselectivity was detected in Huahong apples. The present study will provide additional information that contributes to the comprehensive evaluation of the risks posed by the application of chiral difenoconazole in agricultural production practices.

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

References

  1. Bhat M, Wani AA, Mukhtar M, Sherwani A, Bhat AH, Showkat A (2015) Dissipation patterns of the fungicide difenoconazole (25% EC) in apples grown in Kashmir. India. Environ Monit Assess 187:398

    Article  CAS  Google Scholar 

  2. Chen ZL, Dong FS, Xu J, Liu XG, Cheng YP, Liu N, Tao Y, Pan XL, Zheng YQ (2014) Stereoselective separation and pharmacokinetic dissipation of the chiral neonicotinoid sulfoxaflor in soil by ultraperformance convergence chromatography/tandem mass spectrometry. Anal Bioanal Chem 406:6677–6690

    Article  CAS  Google Scholar 

  3. DG-SANTE (2017) Directorate General for Health and Food Safety. Guidance document on analytical quality control and validation procedures for pesticide residues analysis in food and feed, vol SANTE/11813/2017.

  4. Dong FS, Cheng L, Liu XG, Xu J, Li J, Li YB, Kong ZQ, Jian Q, Zheng YQ (2012) Enantioselective analysis of triazole fungicide myclobutanil in cucumber and soil under different application modes by chiral liquid chromatography/tandem mass spectrometry. J Agr Food Chem 60:1929–1936

    Article  CAS  Google Scholar 

  5. Dong FS, Li J, Chankvetadze B, Cheng YP, Xu J, Liu XG, Li YB, Chen X, Bertucci C, Tedesco D, Zanasi R, Zheng YQ (2013) Chiral triazole fungicide difenoconazole: absolute stereochemistry, stereoselective bioactivity, aquatic toxicity, and environmental behavior in vegetables and soil. Environ Sci Technol 47:3386–3394

    Article  CAS  Google Scholar 

  6. Guo C, Li JZ, Guo BY, Wang HL (2010) Determination and safety evaluation of difenoconazole residues in apples and soils. B Environ Contam Tox 85:427–431

    Article  CAS  Google Scholar 

  7. He M, Jia CH, Zhao EC, Chen L, Yu PZ, Jing JJ, Zheng YQ (2016) Concentrations and dissipation of difenoconazole and fluxapyroxad residues in apples and soil, determined by ultrahigh-performance liquid chromatography electrospray ionization tandem mass spectrometry. Environ Sci Pollut R 23:5618–5626

    Article  CAS  Google Scholar 

  8. Li J, Dong FS, Cheng YP, Liu XG, Xu J, Li YB, Chen X, Kong ZQ, Zheng YQ (2012a) Simultaneous enantioselective determination of triazole fungicide difenoconazole and its main chiral metabolite in vegetables and soil by normal-phase high-performance liquid chromatography. Anal Bioanal Chem 404:2017–2031

    Article  CAS  Google Scholar 

  9. Li YB, Dong FS, Liu XG, Xu J, Li J, Kong ZQ, Chen X, Zheng YQ (2012b) 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 

  10. Li YB, Dong FS, Liu XG, Xu J, Han YT, Zheng YQ (2015) Enantioselectivity in tebuconazole and myclobutanil non-target toxicity and degradation in soils. Chemosphere 122:145–153

    Article  CAS  Google Scholar 

  11. Liu N, Dong FS, Xu J, Liu XG, Chen ZL, Tao Y, Pan XL, Chen XX, Zheng YQ (2015) Stereoselective determination of tebuconazole in water and zebrafish by supercritical fluid chromatography tandem mass spectrometry. J Agr Food Chem 63:6297–6303

    Article  CAS  Google Scholar 

  12. Qi SZ, Chen XF, Liu Y, Jiang JZ, Wang CJ (2015) Comparative toxicity of rac- and S-tebuconazole to Daphnia magna. J Environ Sci Heal B 50:456–462

    Article  CAS  Google Scholar 

  13. Sanderson JT (2006) The steroid hormone biosynthesis pathway as a target for endocrine-disrupting chemicals. Toxicol Sci 94:3–21

    Article  CAS  Google Scholar 

  14. Yun YZ, Yu FW, Wang N, Chen HG, Yin YN, Ma ZH (2012) Sensitivity to silthiofam, tebuconazole and difenoconazole of Gaeumannomyces graminis var. tritici isolates from China. Pest Manag Sci 68:1156–1163

    Article  CAS  Google Scholar 

  15. Zhang Q, Hua XD, Yang Y, Yin W, Tian MM, Shi HY, Wang MH (2015a) Stereoselective degradation of flutriafol and tebuconazole in grape. Environ Sci Pollut R 22:4350–4358

    Article  CAS  Google Scholar 

  16. Zhang ZY, Jiang W, Jian Q, Song WC, Zheng ZT, Wang DL, Liu XJ (2015b) Residues and dissipation kinetics of triazole fungicides difenoconazole and propiconazole in wheat and soil in Chinese fields. Food Chem 168:396–403

    Article  CAS  Google Scholar 

  17. Zhang LM, Dong XC, Wang CG, Zuo ZH, Chen M (2017) Bioaccumulation and the expression of hepatic cytochrome P450 genes in marine medaka (Oryzias melastigma) exposed to difenoconazole. J Environ Sci China 52:98–104

    Article  Google Scholar 

  18. Zhou Y, Li L, Lin K, Zhu XP, Liu WP (2009) Enantiomer separation of triazole fungicides by high-performance liquid chromatography. Chirality 21:421–427

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the earmarked fund for China Agriculture Research System (CARS-27), the Agricultural Science and Technology Innovation Program of Chinese Academy of Agricultural Sciences (CAAS-ASTIP), and the National Program for Quality and Safety Risk Assessment of Agricultural Products of China (GJFP2017003, GJFP2018003).

Author information

Affiliations

Authors

Corresponding author

Correspondence to Jiyun Nie.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Electronic supplementary material 1 (DOCX 122 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Chang, W., Nie, J. & Yan, Z. Enantioselective Behavior of Chiral Difenoconazole in Apple and Field Soil. Bull Environ Contam Toxicol 103, 501–505 (2019). https://doi.org/10.1007/s00128-019-02652-8

Download citation

Keywords

  • Difenoconazole
  • Enantioselectivity
  • Apples
  • Field soil