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Int. J. Mol. Sci. 2013, 14(11), 22544-22557; doi:10.3390/ijms141122544
Article

Synthesis of 2-Acyloxycyclohexylsulfonamides and Evaluation on Their Fungicidal Activity

1,†
, 2,†
, 1
, 1
, 1
 and 1,*
1 Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China 2 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 / Revised: 31 October 2013 / Accepted: 4 November 2013 / Published: 14 November 2013
(This article belongs to the Section Bioinorganic Chemistry)
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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 2-acyloxycycloalkylsulfonamides; Botrytis cinerea; anti-fungal spectra; structure-activity relationship
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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