Absolute configuration of four chiral isomers of pyrisoxazole and their bioactivity
| Autor: | Chunsheng Cheng, Ma Xiaohua, Yunbo Cong, San-Xi Li, Fanian Shi, Zhenyun Wei, Ziliang Li |
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| Rok vydání: | 2019 |
| Předmět: |
0106 biological sciences
Chemistry Low activity Absolute configuration Biological activity Stereoisomerism General Medicine 01 natural sciences Medicinal chemistry Single Crystal Diffraction Fungicides Industrial 010602 entomology Asymmetric carbon Insect Science Agronomy and Crop Science Single crystal Oxazoles 010606 plant biology & botany |
| Zdroj: | Pest management scienceREFERENCES. 76(11) |
| ISSN: | 1526-4998 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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