Design, synthesis and fungicidal activity of novel 2-substituted aminocycloalkylsulfonamides

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• 作者：Caixiu Liu^a ; ^d ; Xiaojing Yan^c ; ^d ; Minlong Wang^a ; Peiwen Qin^a ; Zhiqiu Qi^a ; Mingshan Ji^a ; Xingyu Liu^b ; P. Vijaya Babu^b ; Xinghai Li^a ; ^{xinghai30@163.com} ; Zi-Ning Cui^b ; ^{ziningcui@scau.edu.cn}
• 关键词：2-Aminocycloalkylsulfonamides ; Botrytis cinerea ; Fungicidal activity ; Structure-activity relationship
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2017
• 出版时间：15 January 2017
• 年：2017
• 卷：27
• 期：2
• 页码：271-276
• 全文大小：1705 K
• 卷排序：27

文摘

A series of novel 2-substituted aminocycloalkylsulfonamides were designed and synthesized by highly selective N-alkylation reaction, whose structures were characterized by 1H NMR, 13C NMR and HRMS. Among them, the configuration of compounds III12 and III20 were confirmed by X-ray single crystal diffraction. Bioassays demonstrated that the title compounds had considerable effects on different strains of Botrytis cinerea and Pyricularia grisea. Comparing with positive control procymidone (EC50 = 10.31 mg/L), compounds III28, III29, III30 and III31 showed excellent fungicidal activity against a strain of B. cinerea (CY-09), with EC50 values of 3.17, 3.04, 2.54 and 1.99 mg/L respectively. Their in vivo fungicidal activities were also better than the positive controls cyprodinil, procymidone, boscalid and carbendazim in pot experiments. Moreover, the fungicidal activity of III28 (EC50 = 4.62 mg/L) against P. grisea was also better than that of the positive control isoprothiolane (EC50 = 6.11 mg/L). Compound III28 would be great promise as a hit compound for further study based on the structure-activity relationship.