Synthesis of 2-acyloxycyclohexylsulfonamides and evaluation on their fungicidal activity.
Eighteen N-substituted phenyl-2-acyloxycyclohexylsulfonamides (III) were designed and synthesized by the reaction of N-substituted phenyl-2-hydroxyl- cycloalkylsulfonamides (I, R(1)) with acyl chloride (II, R(2)) 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.
Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110866, Liaoning, China. jimingshan@163.com.
Xinghai
X
Li
Zining
Z
Cui
Xiaoyuan
X
Chen
Decai
D
Wu
Zhiqiu
Z
Qi
Mingshan
M
Ji
D000935:Antifungal Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000737:chemistry; D020171:Botrytis / Q000187:drug effects* / Q000254:growth & development; D006801:Humans; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development; D018515:Plant Leaves / Q000187:drug effects / Q000382:microbiology; D013449:Sulfonamides / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry
D000935:Antifungal Agents; D013449:Sulfonamides