The production and use of chiral pesticides are triggered by the need for more complex molecules capable of effectively combating a greater spectrum of pests and crop diseases, while sustaining high production yields. Currently, chiral pesticides comprise about 30% of all pesticides in use; however, some pesticide groups such as conazole fungicides (CFs) consist almost exclusively of chiral compounds. CFs are produced and field-applied as racemic (1:1) mixtures of two enantiomers (one chiral center in the molecule) or four diastereoisomers, i.e., two pairs of enantiomers (two chiral centers in the molecule). Research on the stereoselective environmental behavior and effects of chiral pesticides such as CFs has become increasingly important within the fields of environmental chemistry and ecotoxicology. This is motivated by the fact that currently, the fate and effects of chiral pesticides such as CFs that arise due to their stereoselectivity are not fully understood and integrated into risk assessment and regulatory decisions. In order to fill this gap, a summary of the state-of-the-art literature related to the stereospecific fate and effects of CFs is needed. This will also benefit the agrochemistry industry as they enhance their understanding of the environmental implications of CFs which will aid future research and development of chiral products. This review provides a collection of >80 stereoselective studies for CFs related to chiral analytical methods, fungicidal activity, non-target toxicity, and behavior of this broadly used pesticide class in the soil environment. In addition, the review sheds more light on mechanisms behind stereoselectivity, considers possible agricultural and environmental implications, and suggests future directions for the safe use of chiral CFs and the reduction of their environmental footprint.
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http://dx.doi.org/10.1016/j.scitotenv.2020.141600 | DOI Listing |
J Am Chem Soc
January 2025
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.
Asymmetric catalysis involving a sulfoxide electrophile intermediate presents an efficient methodology for accessing stereogenic-at-sulfur compounds, such as sulfinate esters, sulfinamides, , which have garnered increasing attention in modern pharmaceutical sciences. However, as the aza-analog of sulfoxide electrophiles, the asymmetric issues about electrophilic sulfinimidoyl species remain largely unexplored and represent a significant challenge in sulfur stereochemistry. Herein, we exhibit an anionic stereogenic-at-cobalt(III) complex-catalyzed asymmetric synthesis of chiral sulfinamides via chiral sulfinimidoyl iodide intermediates.
View Article and Find Full Text PDFJ Agric Food Chem
January 2025
School of Pharmaceutical Sciences, Liaoning University, 66 Chongshan Road, Shenyang 110036, Liaoning Province, P. R. China.
Clethodim is a chiral herbicide with two enantiomers. The herbicidal activity of (-)-clethodim is 1.3-2.
View Article and Find Full Text PDFAnal Chem
January 2025
State Key Laboratory of Green Pesticide (CCNU), College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China.
The research of chiral separation technology is of great significance for understanding the origin of life and promoting the application of chiral molecules. Herein, anionic chiral pillar[6]arene and cationic pillar[6]arene were designed and synthesized, and a chiral pillar[6]arene membrane was constructed by layer-by-layer assembly through electrostatic interactions. The transport rates of l and d in this channel were 14.
View Article and Find Full Text PDFJ 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.
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