Synthesis of 2-amino-6-oxocyclohexenylsulfonamides and their activity against Botrytis cinerea |
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Authors: | Li Xing-Hai Ji Ming-Shan Qi Zhi-Qiu Li Xiu-Wei Shen Yu-Xia Gu Zu-Min Zhang Yang Wei Song-Hong Wang Ying-Zi Wang Dao-Quan |
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Institution: | Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang, Liaoning, PR China. lixinghai30@yahoo.cn |
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Abstract: | BACKGROUND: With the objective of exploring the fungicidal activity of 2‐oxocyclohexylsulfonamides (2), a series of novel 2‐amino‐6‐oxocyclohexenylsulfonamides (6 to 23) were synthesised, and their fungicidal activities against Botrytis cinerea Pers. were evaluated in vitro and in vivo. RESULTS: The compounds were characterised by IR, 1H NMR and elemental analysis. Bioassay results of mycelial growth showed that compounds 6 to 23 had a moderate antifungal activity against B. cinerea. N‐(2‐methylphenyl)‐2‐(2‐methylphenylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (13) and N‐(2‐chlorophenyl)‐2‐(2‐chlorophenylamino)‐6‐oxocyclohexenylsulfonamide (21) showed best antifungal activities, with EC50 values of 8.05 and 10.56 µg mL?1 respectively. Commercial fungicide procymidone provided an EC50 value of 0.63 µg mL?1. The conidial germination assay showed that most of compounds 6 to 23 possessed excellent inhibition of spore germination and germ‐tube elongation of conidia of B. cinerea. For in vivo control of B. cinerea colonising cucumber leaves, the compound N‐cyclohexyl‐2‐(cyclohexylamino)‐4,4‐dimethyl‐6‐oxocyclohexenylsulfonamide (19) showed a better control effect than the commercial fungicide procymidone. CONCLUSION: The present work demonstrated that 2‐amino‐6‐oxocyclohexenylsulfonamides can be used as possible new lead compounds for further developing novel fungicides against B. cinerea. Copyright © 2011 Society of Chemical Industry |
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Keywords: | 2‐amino‐6‐oxocyclohexenylsulfonamides synthesis Botrytis cinerea fungicidal activity |
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