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Enantioselective hydrolysis and photolysis of mandipropamid in different aquatic environments — evaluation of influencing factors

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Abstract

The hydrolysis and photolysis of the chiral fungicide mandipropamid were investigated, and the potential enantioselectivity of mandipropamid in solutions was further assessed. The aqueous solutions were filtered and directly injected into the liquid chromatography with tandem mass spectrometry. In the hydrolysis experiments, mandipropamid enantiomers hydrolyzed slowly in aquatic solutions with half-lives > 200 days; nevertheless, rise of the pH and incubation temperature could increase the hydrolysis rates more than 1.1 times (half-lives decreased from 495.1 to 216.6 days). Compared with the hydrolysis results, photolysis was found to be the main degradation pathway for mandipropamid in different solutions (half-lives < 14 h, except in pH = 5.05 buffer solution). Organic solvents were able to accelerate the photolysis of mandipropamid, but acidic solutions and the addition of flavonoids or inorganic salts significantly inhibited the photolysis of mandipropamid. During the hydrolysis and photolysis processes, the configuration of mandipropamid enantiomers was stable and five possible transformation products were identified by high resolution mass spectrometry. Due to the enantiomeric fraction values > 0.5, the hydrolysis and photolysis of mandipropamid were enantioselective, and S-( +)-mandipropamid preferentially disspated in certain aqueous solutions. The systematic evaluation of the hydrolysis and photolysis of mandipropamid enantiomers may provide more accurate data for better assessment of environmental and ecological risks in aquatic ecosystems.

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Funding

This study was financially supported by the National Key Research and Development Program of China — grant number 2016YFD0200203-3 and the National Natural Science Foundation of China — grant number 32060629.

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Authors and Affiliations

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025, China

    Jianmin Li, Jiahua Han, Tingting Lan, Shiyin Mu, Deyu Hu & Kankan Zhang

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  1. Jianmin Li
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  2. Jiahua Han
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  3. Tingting Lan
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  4. Shiyin Mu
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  5. Deyu Hu
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  6. Kankan Zhang
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Contributions

J. M. Li and J. H. Han carried out the experiments of mandipropamid hydrolysis and photolysis and were major contributors in writing the manuscript. T. T. Lan and S. Y. Mu analyzed the data. D. Y. Hu supervised the instrument measurements. K. K. Zhang organized and supervised the research and proofread this manuscript.

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Correspondence to Kankan Zhang.

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Li, J., Han, J., Lan, T. et al. Enantioselective hydrolysis and photolysis of mandipropamid in different aquatic environments — evaluation of influencing factors. Environ Sci Pollut Res 29, 60244–60258 (2022). https://doi.org/10.1007/s11356-022-20202-4

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