Synthesis of 2-Acyloxycyclohexylsulfonamides and Evaluation on Their Fungicidal Activity

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.

Synthesis, Fungicidal Activity, and Structure Activity Relationship of β-Acylaminocycloalkylsulfonamides against Botrytis cinerea

“…Substituent benzoyl chlorides ( III- 1~ III- 17), acetyl chlorides ( III- 18~ III- 23), halogenated acetyl chlorides ( III- 24~ III- 27), alkoxylacetyl chlorides ( III- 28~ III -29) were synthesized according to the given method in the ref. 32 .…”

“…In vitro effects of compounds against B. cinerea were evaluated by mycelium growth rate method 30 31 32 . The tested compounds were dissolved in DMSO (dimethyl sulfoxide) and mixed with sterile molten potato dextrose agar (PDA) to a final concentration of 50 mg/L.…”

“…Based on the lead structure of compound L , compounds M and N ( Fig. 3 ) were designed and synthesized with much higher fungicidal activity 30 31 32 .…”

Design, Synthesis and Fungicidal Activity of 2-Substituted Phenyl-2-oxo-, 2-Hydroxy- and 2-Acyloxyethylsulfonamides

“…In our previous work, different scaffolds were introduced onto lead 2-oxocycloalkyl-sulfonamides, and the structure-activity relationships (SAR) were studied [ 29 , 30 , 31 , 32 ]. According to the results and following a program of extension and change of these compounds’ structures, we changed the naphthenic group linked with the sulfur bond in the sulfonamide group into an alkyl chain and found that the ethylsulfonamide group was the essential bioactive moiety and therefore, the ethylsulfonamide group was identified as a key building block for compound activity.…”

Untitled

“…Research in heterocyclic chemistry has gained thrust in recent times because more than half of the biologically active molecules belong to various classes of heterocycles [1][2][3][4][5][6][7][8] . 1, 3-Diaza-heterocycles like pyrimidine and quinazoline derivatives, quinazolinones in particular, have been identified as potential drug molecules against various types of diseases.…”