Stereoselective, Diastereoselective Dissipation and Risk Assessment of Chiral Metconazole in Soybean, Peanut, Cabbage, Celery, Tomato, and Soil

J Agric Food Chem. 2023 Dec 6;71(48):18709-18721. doi: 10.1021/acs.jafc.3c06827. Epub 2023 Nov 27.

Abstract

The stereoselective behaviors and dietary risks of metconazole (MZE) in soil and five vegetables were investigated. The results showed that there was species-specific stereoselective and diastereoselective dissipation, and the half-lives ranged from 0.69 to 8.17 days. cis-(+)-1S,5R-MZE was preferentially dissipated in soybean pods, cabbages, celeries, and tomatoes, which was contrary to soybean plants and soil. trans-(+)-1R,5R-MZE was preferentially dissipated in peanut plants, peanut shells, celeries, and tomatoes, while trans-(-)-1S,5S-MZE was preferentially dissipated in soybean plants. cis-MZE was preferentially dissipated in the test vegetables and soil, except celery. The stereoisomeric excess changes were higher than 10%, indicating that the stereoselectivity and diastereoselectivity should be considered in the risk assessment of MZE in soybean plants, pods, and peanut plants. The acute and chronic dietary intake risks of rac-MZE for different groups of people were acceptable. The preferentially dissipated and high activity cis-(+)-1S,5R-MZE with lower toxicity might be suitable for application as monocase.

Keywords: diastereoselectivity; dissipation; metconazole stereoisomers; risk assessment; stereoselectivity; vegetables.

MeSH terms

  • Apium*
  • Arachis
  • Brassica*
  • Glycine max
  • Humans
  • Risk Assessment
  • Soil
  • Soil Pollutants* / analysis
  • Solanum lycopersicum*
  • Stereoisomerism
  • Vegetables

Substances

  • metconazole
  • Soil
  • Soil Pollutants