A novel series of macrocyclic tetradentate nitrogen donor (N 4 ) ligand 5, 8, 13, 16-tetraoxo- 6, 15-dihydroxy-1, 4, 9, 12-tetraazacyclohexa-decane a nd its transition metal complexes of the type [M(C 12 H 20 O 6 N 4 )Cl 2 ] where M= Cu(II), Ni(II), and Co(II) have been syn thesized by template condensation of malic acid and ethylenediamine. The ligand and its complexes have been characterized on the basis of elemental analysis, F TIR, 1 H NMR, ESI MS, TG/DTA, UV-Vis spectroscopic techniques, conductivity and magnetic measurements. On the basis of these studies, a six coordinate octahedral geometry aroun d the metal ions in the complexes has been proposed. These metal complexes were also tested for their in vitro antifungal activities against some fungal species to assess their inhibiting pote ntial and the activities shown by these complexes were compared with standard drugs.