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Chiral pesticides often undergo enantioselective degradation during food fermentation. In this study, the enantioselective fates of seven chiral pesticides during processing of wine and rice wine were investigated. The results revealed that R-metalaxyl, R-mefentrifluconazole and S-hexaconazole were preferentially degraded during wine processing with EF values of 0.57, 0.78, and 0.43, respectively, whereas S-metalaxyl and R-hexaconazole were preferentially degraded during rice wine processing with EF values of 0.44 and 0.54, respectively. Stereoselectivity was attributed to fermentative bacterial activity. The processing factor (PF) values for the five pesticides ranged from 0.04 to 0.34 during wine processing and from 0.02 to 0.29 during rice wine processing, suggesting that fermentation can mitigate pesticide exposure risks and ensure food safety. This study enhances our understanding of enantioselective fate of chiral pesticides during fermented food processing, provides guidance for the application of chiral pesticides, and enables the dietary risk of chiral pesticides in processed products to be assessed more accurately.
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http://dx.doi.org/10.1002/chir.70018 | DOI Listing |
J Chromatogr Sci
August 2025
Department of Chemistry, Yogi Vemana University, Vemana Puram, Ganganapalle, Kadapa (Dist), Andhra Pradesh 516005 Andhra Pradesh 516005, India.
A novel and validated reverse-phase high-performance liquid chromatography (RP-HPLC) approach was established for the concurrent measurement of cyproconazole (CYP) isomers and tebuconazole (TBZ) in suspension concentrate (SC) agrochemical formulations. The approach employed a C18 column with a gradient elution of 0.1% formic acid in water and methanol, attaining baseline resolution of CYP isomer-1, isomer-2 and TBZ without requiring chiral columns or sample pretreatment.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2025
State Key Laboratory of Green Pesticide; Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Huaxi District, Guiyang, 550025, China.
In contrast to the notable advancements focusing on the preparation of optically enriched S(IV) frameworks in recent years, achieving catalyst stereocontrol over S(VI) stereogenicity to generate chiral S(VI) scaffolds remains a largely underexplored challenge. Herein, we document a new activation mode of isothiourea organocatalysis for the highly enantioselective synthesis of S(VI)-chiral sulfonimidates. This method involves the covalent activation of racemic S(VI) sulfonimidoyl chlorides through the formation of a pivotal isothiourea-bound sulfonimidoyl intermediate.
View Article and Find Full Text PDFJ Agric Food Chem
September 2025
State Key Laboratory of Green Pesticide, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, P. R. China.
Mesoionic insecticides have emerged as promising pest nAChR modulators devoid of cross-resistance with neonicotinoids, demonstrating exceptional efficacy against sap-feeding insects. Nevertheless, the tetrahydrothiazolo[3,2-]pyrimidine structure remains underexplored within this chemotype. Here, we report an indole-based scaffold hopping of tetrahydrothiazolo[3,2-]pyrimidine, which leads to the development of a series of novel mesoionics.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
Key Laboratory of Marine Drugs, Ministry of Education; School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
Phosphorus(V) stereogenic centers are prevalent in various pharmaceuticals, pesticides, and functional materials. Herein, we report an organophosphine-catalyzed asymmetric S2' substitution between unsymmetrical phosphine oxides and Morita-Baylis-Hillman adducts through an umpolung addition pathway, allowing the efficient construction of functionalized adjacent P(V)-C chiral stereogenic centers. A chiral phosphine catalyst, derived from an amino acid, enabled the formation of the desired products in high yields (up to 99%) and excellent enantioselectivities (up to 97% ee).
View Article and Find Full Text PDFSci Adv
August 2025
State Key Laboratory of Green Pesticide, Center for Research and Development of Fine Chemicals, Guizhou University, Huaxi District, Guiyang 550025, P. R. China.
Sulfur plays a pivotal role across diverse fields owing to its distinctive chemical and biological properties, thereby propelling the development of stereoselective synthesis of enantioenriched S(IV)-stereogenic scaffolds. While oxidative strategies for generating S-chiral frameworks have witnessed emerging development, the catalytic reduction of S(VI) species to furnish enantioenriched S(IV) scaffolds remains largely overlooked. Herein, we present an enantioselective catalytic method to access S(IV)-stereogenic sulfinimidate ester scaffolds through a distinct catalytic asymmetric formal reductive transformation of S(VI)-sulfonimidoyl chlorides.
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