2,4-dinitrobenzenesulfenyl chloride was prepared by reacting 2,4-dinitrochlorobenzene with
benzyl mercaptan and subsequently cracking the formed 2,4-dinitrophenyl benzyl sulphide with sulfuryl chloride.
The prepared 2,4-dinitrobenzenesulfenyl chloride reacted with series of primary alcohols in the presence of pyridine
to give alkyl-2,4-dinitrobenzenesulfenate esters. The synthesized compounds were characterized by elemental
analysis, thin layer chromatography (TLC), fourier-transform infrared,
1H and
13C nuclear magnetic resonance
spectroscopic techniques. In vitro fungicidal assay of these alkyl sulfenate esters against
Aspergillus flavus
,
Rhizopus
stolonifer
and
Fusarium oxysporum
showed that all the synthesized sulfenate esters were fungicidal. Increase in
chain length of the alkyl substituents was found to reduce the fungicidal activity of the alkyl sulfenate esters.
Presence of an hydroxyl group increased the fungicidal activity of ethyl-2,4-dinitrobenzenesulfenate by 5-to 10-fold.
