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Absolute configuration of four chiral isomers of pyrisoxazole and their bioactivity. 2020

Ziliang Li, and Yunbo Cong, and Xiaohua Ma, and Zhenyun Wei, and Chunsheng Cheng, and Fanian Shi, and Sanxi Li
School of Material Science and Engineering, Shenyang University of Technology, Shenyang, P. R. China.

BACKGROUND Pyrisoxazole is a fungicide that has two chiral carbon atoms and four isomers: (3S,5R)-, (3R,5S)-, (3S,5S)-, and (3R,5R)-pyrisoxazole. RESULTS Pure crystals of four pyrisoxazole isomers were prepared by chiral separation and single-crystal cultivation. Their absolute configurations were established by X-ray single crystal diffraction analysis. Bioassays indicated that compound (3S,5R)-pyrisoxazole showed excellent fungicidal activity with a median effective concentration (EC50 ) value of 0.14 μg mL-1 and protective activity with an EC50 value of 13.29 μg mL-1 . These values are superior to the commercial fungicides boscalid and racemic pyrisoxazole. CONCLUSIONS The biological activity of racemic pyrisoxazole is due almost exclusively to the isomer (3S,5R)-pyrisoxazole; the other three isomers had very low activity. © 2020 Society of Chemical Industry.

UI MeSH Term Description Entries
D010080 Oxazoles Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions. Oxazole,1,3-Oxazolium-5-Oxides,Munchnones,1,3 Oxazolium 5 Oxides
D005659 Fungicides, Industrial Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. Industrial Fungicides
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

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