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A novel series of complexes of the type [M(C28H24N4)X]X2, where M = Cr(III), Fe(III) or Mn(III), X = Cl−, NO3−, CH3COO− and (C28H24N4) corresponds to the tetradentate macrocyclic ligand, were synthesized in methanolic media by the template condensation of 1,8-diaminonaphthalene and 2,3-butanedione (diacetyl) in the presence of trivalent metal salts. The complexes were characterized by elemental analyses, conductance and magnetic measurements, and UV/Vis and IR spectroscopy. Based on these studies, a five-coordinate square pyramidal geometry for all the prepared complexes is proposed. All the synthesized macrocyclic complexes were tested for their in vitro antifungal activity against some fungal strains viz. Aspergillus niger and A. fumigatus. The results obtained were compared with the standard antifungal drug fluconazole.