Design,synthesis and fungicidal activity of novel 2-substituted aminocycloalkylsulfonamides |
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Authors: | Caixiu Liu Xiaojing Yan Minlong Wang Peiwen Qin Zhiqiu Qi Mingshan Ji Xingyu Liu P. Vijaya Babu Xinghai Li Zi-Ning Cui |
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Affiliation: | 1. Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China;2. State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou 510642, China;3. Key Laboratory of Integrated Pest Management in Crops, Ministry of Agriculture, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China |
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Abstract: | 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. |
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Keywords: | 2-Aminocycloalkylsulfonamides Fungicidal activity Structure-activity relationship |
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