Synthesis of 2-Acyloxycyclohexylsulfonamides and Evaluation on Their Fungicidal Activity

• Main Authors: Zhiqiu Qi, Mingshan Ji, Decai Wu, Xiaoyuan Chen, Zining Cui, Xinghai Li
• Format: Article
• Language: English
• Published: MDPI AG 2013-11-01
• Series: International Journal of Molecular Sciences
• Subjects: 2-acyloxycycloalkylsulfonamides; Botrytis cinerea; anti-fungal spectra; structure-activity relationship
• Online Access: http://www.mdpi.com/1422-0067/14/11/22544

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.