Synthesis, Fungicidal Activity, and Structure-Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides.
ABSTRACT To explore new potential fungicides, a series of novel compounds, including 11 2-oxocycloalkylsulfonamide (3) and 21 2-hydroxycycloalkylsulfonamide (4) derivatives, were synthesized and their structures were confirmed by (1)H nuclear magnetic resonance (NMR), infrared (IR), and elemental analysis. The results of the bioassay showed that the compounds 3 and 4 possessed excellent fungicidal activity against Botrytis cinerea Pers. both in vitro and in vivo. The fungicidal activity of the compounds with 7- or 8-membered rings is better than those with 5-, 6-, or 12-membered rings. According to the results of the mycelium growth rate test, the EC(50) values of the compounds 3C, 4C, 3D, and 4D were 0.80, 0.85, 1.22, and 1.09 μg/mL, respectively, and similar to or better than commercial fungicide procymidone. The bioassay results of spore germination indicated that most of the compounds exhibited obvious inhibitory effects against B. cinerea and the inhibition rates of 2-oxocycloalkylsulfonamides were higher than 2-hydroxycycloalkylsulfonamides, among them. The EC(50) values of compounds 3A, 3B(17), 3E, and 4A were 4.21, 4.21 3.24, and 5.29 μg/mL, respectively. Those compounds containing 5- or 6-membered rings showed better activity than those containing 7-, 8-, or 12-membered rings. Furthermore, the results of the pot culture test showed that almost all of the compounds had effective control activity in vivo and 2-hydroxycycloalkylsulfonamides were obviously superior to 2-oxocycloalkylsulfonamides. The compounds 3E, 4C and 4D presented higher control efficacy than procymidone and pyrimethanil against gray mold disease on cucumber plants.
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ABSTRACT: A new organic–inorganic hybrid SO4[C6H9N2O2S]2, has been synthesized and characterized by X–ray diffraction. This compound crystallizes in the orthorhombic system, spaces group Pbcn. In the title compound, the packing is stabilized by intermolecular N-H…O hydrogen bonds and π-π stacking interactions between the phenyl rings, linking the molecules into three-dimensional network. The in vitro antimicrobial activity of di (4-sulfamoyl-phenyl-ammonium) sulphate was determined by the broth dilution method against several strains selected to define their spectrum and potency. Here we show that the synthetic sulfanilamide exhibits promising antibacterial potency. High inhibition was also detected against Candida albicans. In this paper we firstly showed the antifungal activity of the sulfanilamide against two serious phytopathogenic fungi. Interestingly, the new compound was able to suppress mycelial growth as well as the spores germination of tested fungi, values of spore germination vary from 97.6% to 37.5% respectively for Botrytis cinerea and Fusarium species. The minimal inhibitory concentrations (MIC) ranging from 8 to 100 μg ml-1 and IC50 values varying from 5.81 to less than 100 μg ml-1), showed that the sulfanilamide sulphate had high activity against bacteria, yeast and fungi, compared to others published antifungal compounds.Microbiological Research 01/2013; · 1.99 Impact Factor
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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.International Journal of Molecular Sciences 01/2013; 14(11):22544-57. · 2.46 Impact Factor