As many as 40% of all plant protection products currently used contain chiral active ingredients. Enantiomers of the same pesticide have identical physicochemical properties in an isotropic medium, but they may display different activity and toxicity because of their interaction with enzymes or other naturally occurring asymmetric molecules. This difference may also lead to variations in biotic degradation rates, making one enantiomer more persistent than the other in natural and agricultural environments. In terms of methodological aspects, this critical review describes the most used chiral stationary phases for HPLC enantioseparations of chiral pesticides, pinpointing their strengths and weaknesses. As far as their applicability is concerned, most research has been carried out by means of columns based on derivatized amylose/cellulose due to their rather universal analyte coverage. The chromatographic compatibility with sensitive detection techniques, such as mass spectrometry, has allowed the trace analysis of stereoisomers, revealing ubiquitous occurrence of some chiral pesticides in surface waters, sediments, plants, agricultural soils, roots, fruit and vegetables. The study of their distribution and degradation in various environmental compartments and agricultural soil-plant systems has highlighted the enrichment with one enantiomer over the other in certain matrices following the enantioselective dissipation catalysed by microorganisms or plant enzymes as well as the phenomenon of chiral inversion in some cases. Irrespective of the reliability of a chiral method, such investigations are often hindered by the lack of pure standards of single enantiomers, which makes it difficult to identify their stereochemical configuration and requires precise strategies of quantification. Surely, the research in this field has been grown over the last few years due to the necessity of assessing and limiting risks related to exposure to chiral pesticides, which can be considered emerging contaminants in all aspects.
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http://dx.doi.org/10.1016/j.chroma.2022.463595 | DOI Listing |
J Hazard Mater
December 2024
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Department of Applied Chemistry, China Agricultural University, Beijing 100193, PR China. Electronic address:
Ipconazole (IPC) is a chiral triazole fungicide and commonly used for disease control in seeds. This study investigated the bioactivity and potential mechanism of ipconazole against pathogenic microorganisms at the chiral perspective. It explored the accumulation behavior of ipconazole enantiomers within the soil-earthworm system and evaluated its toxic effects on earthworms.
View Article and Find Full Text PDFMolecules
December 2024
Faculty of Medicine, The John Paul II Catholic University of Lublin, Konstantynów 1J/4.03, 20-708 Lublin, Poland.
Improved methods for the synthesis of nicotine are of great importance due to the wide range of applications of synthetic nicotine, which is free from contamination with nitrosamines. Herein, we present a four-step chemical synthesis of ()-nicotine, involving the reduction in myosmine, enantiomeric separation of nornicotine, and subsequent methylation of the appropriate enantiomer of nornicotine obtained. The reduction in myosmine was investigated using both electrochemical and chemical approaches, achieving up to 90% yields of pure nornicotine.
View Article and Find Full Text PDFJ Agric Food Chem
December 2024
School of Pharmacy, Shenyang Medical College, Shenyang 110034, China.
Propiconazole (PRO) is a chiral triazole fungicide that has been widely used for several years. However, its metabolic characteristics and hepatotoxicity in the chiral level environment remain unclear. In this study, the stereoselective behavior of PRO was investigated by using liver microsome incubation, cell viability assay, inhalation exposure, and molecular docking.
View Article and Find Full Text PDFJ Hazard Mater
November 2024
Key Laboratory of Pollution Exposure and Health Intervention of Zhejiang Province, Interdisciplinary Research Academy (IRA), Zhejiang Shuren University, Hangzhou 310015, China. Electronic address:
Angew Chem Int Ed Engl
December 2024
Department of Applied Chemistry, Anhui Province Engineering Laboratory for Green Pesticide Development and Application, and Anhui Province Key Laboratory of Crop Integrated Pest Management, Anhui Agricultural University, Hefei, 230036, China.
An efficient enantioselective coupling reaction between sulfenamides and cyclic diaryliodonium salts is established via adaptive Cu/anionic stereogenic-at-Co(III) complex combined catalysis, precisely synthesizing a broad range of axially chiral sulfilimines with excellent enantioselectivities, diastereoselectivities, regioselectivities, and chemoselectivities (67 examples under same conditions, up to 98 % ee). The following thermodynamically controlled pyramidal inversion enables efficient stereodivegent synthesis of all four stereoisomers. Mechanistic studies suggest that anionic stereogenic-at-cobalt(III) complexes serve as counteranions of diaryliodonium and anionic ligand of Cu(I) catalyst simultaneously, which could be regarded as an explanation for outstanding selectivities.
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