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Synthesis of 2-Acyloxycyclohexylsulfonamides and Evaluation on Their Fungicidal Activity
Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China
Guangdong Province Key Laboratory of Microbial Signals and Disease Control, Department of Plant Pathology, College of Natural Resources and Environment, South China Agricultural University, Guangzhou 510642, Guangdong, China
These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 8 October 2013; in revised form: 31 October 2013 / Accepted: 4 November 2013 / Published: 14 November 2013
Abstract: Eighteen N-substituted phenyl-2-acyloxycyclohexylsulfonamides (III) were designed and synthesized by the reaction of N-substituted phenyl-2-hydroxyl- cycloalkylsulfonamides (I, R1) with acyl chloride (II, R2) in dichloromethane under the catalysis of TMEDA and molecular sieve. High fungicidal active compound N-(2,4,5-trichlorophenyl)-2-(2-ethoxyacetoxy) cyclohexylsulfonamide (III-18) was screened out. Mycelia growth assay against the Botrytis cinerea exhibited that EC50 and EC80 of compound III-18 were 4.17 and 17.15 μg mL−1 respectively, which was better than the commercial fungicide procymidone (EC50 = 4.46 μg mL−1 and EC80 = 35.02 μg mL−1). For in vivo activity against B. cinerea in living leaf of cucumber, the control effect of compound III-18 was better than the fungicide cyprodinil. In addition, this new compound had broader fungicidal spectra than chlorothalonil.
Keywords: 2-acyloxycycloalkylsulfonamides; Botrytis cinerea; anti-fungal spectra; structure-activity relationship
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Li, X.; Cui, Z.; Chen, X.; Wu, D.; Qi, Z.; Ji, M. Synthesis of 2-Acyloxycyclohexylsulfonamides and Evaluation on Their Fungicidal Activity. Int. J. Mol. Sci. 2013, 14, 22544-22557.
Li X, Cui Z, Chen X, Wu D, Qi Z, Ji M. Synthesis of 2-Acyloxycyclohexylsulfonamides and Evaluation on Their Fungicidal Activity. International Journal of Molecular Sciences. 2013; 14(11):22544-22557.
Li, Xinghai; Cui, Zining; Chen, Xiaoyuan; Wu, Decai; Qi, Zhiqiu; Ji, Mingshan. 2013. "Synthesis of 2-Acyloxycyclohexylsulfonamides and Evaluation on Their Fungicidal Activity." Int. J. Mol. Sci. 14, no. 11: 22544-22557.