Four copper(II) complexes have been prepared using macrocyclic ligands. The macrocyclic ligands have been synthesized by the condensation reaction of diethyl phthalate with Schiff bases derived from o-phenylene diamine and Knoevenagel condensed ${eta}-ketoanilides$ (obtained by the condensation of acetoacetanilide and substituted benzaldehydes). The ligands and copper complexes have been characterized on the basis of Microanalytical, Mass, UV-Vis., IR and CV spectral studies, as well as conductivity data. On the basis of spectral studies, a square-planar geometry for the copper complexes has been proposed. The in vitro antifungal activities of the compounds were tested against fungi such as Aspergillus niger, Rhizopus stolonifer, Aspergillus flavus, Rhizoctonia bataicola and Candida albicans. All the synthesized copper complexes showed stronger antifungal activities than free ligands. The minimum inhibitory concentrations (MIC) of the copper complexes were found in the range of $8{sim}28;{mu}g/ml$. These compounds represent a novel class of metal-based antifungal agents which provide opportunities for a large number of synthetic variations for modulation of the activities.