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Enantioselective fate of mandipropamid in grape and during processing of grape wine

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Abstract

Enantioselective monitoring of chiral fungicide mandipropamid enantiomers were carried out in grapes and wine-making process. The enantiomers of mandipropamid were separated on a Lux Cellulose-2 column and determined by ultra-high-performance liquid chromatography coupled with tandem mass spectrometry (UHPLC–MS/MS). The processing procedure included washing, fermentation, and clarification. Significant enantioselectivity was observed in grape under field conditions and during wine-making processing. The half-lives of R-mandipropamid and S-mandipropamid were 5.63 days and 7.79 days under field conditions 43.3 h and 69.3 h during wine-making processing, respectively. The EF values ranged from 0.498 to 0.283 in grape under field conditions, and the EF values were from 0.458 (0 h) to 0.362 (312 h) during the whole fermentation process. The results indicated that R-mandipropamid degraded faster than S-mandipropamid in grape under field conditions and during the fermentation process. The processing factors (PFs) were less than 1 for each procedure, and the PF ranged from 0.005 to 0.025 in the overall process, which indicated that the wine-making process can reduce mandipropamid residue in grape wine. The results of this study could help facilitate more accurate risk assessments of mandipropamid in table grapes and during wine-making process.

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References

  • Amvrazi EG, Albanis TA (2008) Multiclass pesticide determination in olives and their processing factors in olive oil: comparison of different olive oil extraction systems. J Agric Food Chem 56(14):5700–5709

    Article  CAS  Google Scholar 

  • Angioni A, Dedola F, Garau VL, Schirra M, Caboni P (2011) Fate of iprovalicarb, indoxacarb, and boscalid residues in grapes and wine by GC-ITMS analysis. J Agric Food Chem 59(12):6806–6812

    Article  CAS  Google Scholar 

  • Cabras P, Angioni A (2000) Pesticide residues in grapes, wine, and their processing products. J Agric Food Chem 48(4):967–973

    Article  CAS  Google Scholar 

  • Choung MG, Ahn KG, Kim GP, Hwang YS, Kwon CH, Kang IK, Lee YD (2016) Dissipation pattern of a fungicide mandipropamid in Korean cabbage at different harvest times under greenhouse conditions. Korean J Hortic Sci Technol 34:644–654

    CAS  Google Scholar 

  • Cooper J, Dobson H (2007) The benefits of pesticides to mankind and the environment. Crop Prot 26(9):1337–1348

    Article  CAS  Google Scholar 

  • Fantke P, Juraske R (2013) Variability of pesticide dissipation half-lives in plants. Environ Sci Technol 47(8):3548–3562

    Article  CAS  Google Scholar 

  • FAO/WHO (2006) Updating the principles and methods of risk assessment: MRLs forpesticides and veterinary drugs. FAO, Rome

    Google Scholar 

  • Garrison A (2006) Probing the enantioselectivity of chiral pesticides. Environ Sci Technol 40(1):16–23

    Article  Google Scholar 

  • Gonzalez-Rodriguez R, Rial-Otero R, Cancho-Grande B, Gonzalez-Barreiro C, Simal-Gandara J (2011) A review on the fate of pesticides during the processes within the food-production chain. Crit Rev Food Sci Nutr 51(2):99–114

    Article  CAS  Google Scholar 

  • Han Y, Xu J, Dong F, Li W, Liu X, Li Y, Kong Z, Zhu Y, Liu N, Zheng Y (2013) The fate of spirotetramat and its metabolite spirotetramat-enol in apple samples during apple cider processing. Food Control 34(2):283–290

    Article  CAS  Google Scholar 

  • Han Y, Dong F, Xu J, Liu X, Li Y, Kong Z, Liang X, Liu N, Zheng Y (2014) Residue change of pyridaben in apple samples during apple cider processing. Food Control 37(1):240–244

    Article  CAS  Google Scholar 

  • Hercegova A, Domotorova M, Hrouzkova S, Matisova E (2007) Study on pesticide residues in apples, apple-based baby food, and their behaviour during processing using fast GCeMS multiresidue analysis. Int J Environ Anal Chem 87(13–14):957–969

    Article  CAS  Google Scholar 

  • Hwang ES, Cash J, Zabik M (2002) Degradation of mancozeb and ethylenethiourea in apples due to postharvest treatments and processing. J Food Sci 67(9):3295–3300

    Article  CAS  Google Scholar 

  • Kaushik G, Satya S, Naik SN (2009) Food processing a tool to pesticide residue dissipation – a review. Food Res Int 42(1):26–40

    Article  CAS  Google Scholar 

  • Kong Z, Dong F, Xu J, Liu X, Zhang C, Li J, Li Y, Chen X, Shan W, Zheng Y (2012) Determination of difenoconazole residue in tomato during home canning by UPLC-MS/MS. Food Control 23(2):542–546

    Article  CAS  Google Scholar 

  • Krol WJ, Arsenault TL, Pylypiw HM Jr, Mattina MJI (2000) Reduction of pesticide residues on produce by rinsing. J Agric Food Chem 48(10):4666–4670

    Article  CAS  Google Scholar 

  • Lamberth C, Jeanguenat A, Cederbaum F, De Mesmaeker A, Zeller M, Kempf HJ et al (2008) Multicomponent reactions in fungicide research: the discovery of mandipropamid. Bioorg Med Chem 16(3):1531–1545

    Article  CAS  Google Scholar 

  • Li Y, Dong F, Liu X, Xu J, Chen X, Han Y, Cheng Y, Jian Q, Zheng Y (2013) Enantioselective separation and transformation of metalaxyl and its major metabolite metalaxyl acid in tomato and cucumber. Food Chem 141(1):10–17

    Article  CAS  Google Scholar 

  • Li Y, Dong F, Liu X, Xu J, Han Y, Zheng Y (2014) Chiral fungicide triadimefon and triadimenol: stereoselective transformation in greenhouse crops and soil, and toxicity to Daphnia magna. J Hazard Mater 265:115–123

    Article  CAS  Google Scholar 

  • Lu Y, Diao J, Xu G, Zhang Y, Xu P, Wang P et al (2011) Stereoselective degradation of diclofop-methyl during alcohol fermentation process. Chirality 23(5):424–428

    Article  CAS  Google Scholar 

  • Malhat FM, Mahmoud HA (2012) Dissipation and residues of mandipropamid in grape using QuEChERS methodology and HPLC-DAD. ISRN Anal Chem 2012:1–5

    Article  Google Scholar 

  • Noelia B, Laura C, Raquel R, Beatriz C, Jesus S (2018) Fungicide residues affect the sensory properties and flavonoid composition of red wine. J Food Compos Anal 66:185–192

    Article  Google Scholar 

  • Noelia B, Raquel R, Miguel AC, Jose O, Jesus S (2019) Dissipation of three fungicides and their effects on anthocyanins and color of monastrell red wines. Int J Mol Sci 20(6):1447

    Article  Google Scholar 

  • OECD (2007) Guidance document on pesticide residue analytical methods (pp. 18–28). ENV/JM/MONO(2007), 17

  • OECD (2008) OECD guideline for the testing of chemicals. Magnitude of the pesticide residues in processed commodities. NO.508

  • Pan X, Dong F, Xu J, Liu X, Chen Z, Zheng Y (2016) Stereoselective analysis of novel chiral fungicide pyrisoxazole in cucumber, tomato and soil under different application methods with supercritical fluid chromatography/tandem mass spectrometry. J Hazard Mater 311:115–124

    Article  CAS  Google Scholar 

  • Pan X, Dong F, Liu N, Cheng Y, Xu J, Liu X, Wu X, Chen Z, Zheng Y (2018) The fate and enantioselective behavior of zoxamide during wine-making process. Food Chem 248:14–20

    Article  CAS  Google Scholar 

  • Raquel N, Tania F, Thais S, Carmen G, Beatriz C, Diego-Augusto C, Maria G, Marai-Teresa M, Jesus S, Jesus S (2016) Dissipation of fungicide residues during winemaking and their effects on fermentation and the volatile composition of wines. J Agric Food Chem 64(6):1344–1354

    Article  Google Scholar 

  • Rasmusssen R, Poulsen ME, Hansen H (2003) Distribution of multiple pesticide residues in apple segments after home processing. Food Addit Contam 20(11):1044–1063

    Article  CAS  Google Scholar 

  • Sekhon B (2009) Chiral pesticides. J Pest Sci 34(1):1–12

    Article  CAS  Google Scholar 

  • Thais S, Maria F, Carmen G, Jesus S, Betariz C, Raquel R (2019) Impact of mepanipyrim and tetraconazole in Mencía wines on the biosynthesis of volatile compounds during the winemaking process. Food Chem 300:125223

    Article  Google Scholar 

  • Ulrich EM, Morrison CN, Goldsmith MR, Foreman WT (2012) Chiral pesticides: identification, description, and environmental implications. Rev Environ Contam Toxicol 217:1–74

    CAS  Google Scholar 

  • Xu C, Wang JJ, Liu WP, Sheng GD, Tu YJ, Ma Y (2008) Separation and aquatic toxicity of enantiomers of the pyrethroid insecticide lambda-cyhalothrin. Environ Toxicol Chem 27(1):174–181

    Article  CAS  Google Scholar 

  • Ye J, Zhao M, Liu J, Liu W (2010) Enantioselectivity in environmental risk assessment of modern chiral pesticides. Environ Pollut 158(7):2371–2383

    Article  CAS  Google Scholar 

  • Zhang H, Wang XY, Wang XQ, Qian MR, Xu MF, Xu H et al (2014) Enantioselective determination of carboxyl acid amide fungicide mandipropamid in vegetables and fruits by chiral LC coupled with MS/MS. J Sep Sci 37(3):211–218

    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(284):65–72

    CAS  Google Scholar 

Download references

Funding

This work was supported by Agricultural Science and Technology Innovation Program of CAAS (CAAS- ZDRW202011) and the National Program for Quality and Safety Risk Assessment of Agricultural Products of China (GJFP2019011).

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Correspondence to Guofeng Xu.

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Xu, G., Jia, X., Zhang, H. et al. Enantioselective fate of mandipropamid in grape and during processing of grape wine. Environ Sci Pollut Res 27, 40148–40155 (2020). https://doi.org/10.1007/s11356-020-10061-2

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  • DOI: https://doi.org/10.1007/s11356-020-10061-2

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