New Study Reveals Enhanced Chiral Separation Method for Metconazole Fungicide

The appearance of fungi in crops has a deleterious impact on the agriculture and food industries. To mitigate this problem, farmers normally use fungicides to prevent fungal infections from impacting their crops. One of these fungicides is metconazole.

Sooty mould black mould on wheat ears, Cladosporium herbarum Alternaria alternata. Cereal diseases, ear diseases. Fungal disease affecting all species and varieties of cereals. Produced mycotoxin. | Image Credit: © Tomasz - stock.adobe.com

In a recent study published in the Journal of Separation Science, lead author Xiang-Bing Xu from the Wuhan Institute of Technology delves into the intricate process of chiral separation for metconazole, a widely used fungicide known for its efficacy in controlling various wheat diseases (1).

Metconazole, a chiral triazole fungicide, has garnered significant attention for its effectiveness against wheat leaf rust, powdery mildew, Fusarium head blight, and other fungal infections (1). In the study, Xu optimized the chiral separation process for metconazole, considering factors such as chiral stationary phases, alcoholic modifiers, and column temperature (1).

Xu’s study revealed some important findings. It showed that the amylose tris(3,5-dimethylphenylcarbamate)-coated chiral stationary phase in a CO₂/ethanol mixture demonstrated excellent chiral recognition ability (1). This discovery lays the groundwork for more efficient chiral separation techniques, which is important for getting optically pure metconazole products (1).

Two chromatographic techniques, supercritical fluid chromatography (SFC) and high-performance liquid chromatography (HPLC), were used for the separation method. Through this process, the researchers achieved enantiomeric excess values of over 98% for all four stereoisomers of metconazole, ensuring high purity in the separated compounds (1).

Xu also investigated investigating the enantioselective cytotoxicity of cis-metconazole against HepG2 cells. The results revealed varying levels of cell proliferation toxicity, with (1R, 5S)-metconazole exhibiting the highest toxicity, followed by (1S, 5R)-metconazole, and the mixture (1). These findings not only advance the understanding of chiral separation techniques, but they also contribute valuable insights into the environmental risk assessment of metconazole.

Overall, the study by Xiang-Bing Xu sheds light on the chiral separation process for metconazole, presenting an improved method for preparative separation of optically pure products and their subsequent environmental evaluation (1).

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Reference

(1) Xu, X.-B. Chiral Analysis and Semi-preparative Separation of Metconazole Stereoisomers by Supercritical Fluid Chromatography and Cytotoxicity Assessment in vitro. J. Sep. Sci. 2023, ASAP. DOI: 10.1002/jssc.202300655