Two chelate-forming Schiff bases derived from 4-aminoantipyrine with 4-aminobenzoic acid and benzoin, namely (Z)-4-(4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-ylideneamino)benzoic acid (HL1) and 4-((E)-4-((E)-((R)-2-hydroxy-1,2-diphenylethylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-ylideneamino)benzoic acid (H2L2) were prepared and complexed with copper(II), nickel(II), cobalt(II), manganese(II) and mercury(II)chlorides in ethanol. The M(HL1)2Cl2 and M(HL2)2 type complexes could be isolated. The ligands and theirs metal complexes were characterized using elemental analysis, infrared and electronic, 1H and 13C NMR spectroscopy, molar conductance and magnetic moment measurements. The measurements showed that the HL1 ligand is coordinated in their complexes with N,N-bidendate mode, while HL2 ionic ligand in NNO tridentate pattern through the azomethine nitrogen, amino-group and the depotonated hydroxyl group of benzoin. The stability constants of complexes were determined spectrophotometricaly. All the studies reveal a six coordinated octahedral structure of M(HL2)2 type complexes. In vitro tests for antibacterial and antifungal activities showed that most of the prepared compounds display a good activity towards S. aureus, E. coli, B. subtilis, P. aureginosa, A. niger, A. flavus, R. stolonifer and C. albicans .