Chemoselective Reaction of Diethyl Malonate with Benzal-4-acetylanilines and Fungitoxicity of the Products

Condensation of diethyl malonate with benzal-4-acetylanilines (I-X), the compounds containing both imine and ketone moieties, in equimolar ratio resulted in the formation of solid products, identified as diethyl 2-benzylidenemalonate and its derivatives (Ia-Xa) on the basis of elemental analysis and spectral studies. The reaction of I-X with two moles of diethyl malonate also yielded the same products Ia-Xa by a chemoselective attack of diethyl malonate on imine moiety only rather than on both the reactive centres. The synthesized compounds Ia-Xa were evaluated for antifungal potential against A. alternata, C. capsici, F. oxysporum, M. roridum and U. tritici by spore germination inhibition method. Some of the compounds possessed promising fungitoxicity.