A novel tetradentate Schiff base ligand 2,2'-(1E,1'E)-1,1'-(6-chloropyrimidine-2,4-diyl)bis(azan-1-yl-1- ylidene)bis(ethan-1-yl-1-ylidene)diphenol (L) was synthesized by the reaction of 2-hydroxy acetophenone and 4- chloro-2,6-diaminopyrimidine. The structure of the ligand was elucidated by elemental analysis IR, H1NMR and electronic spectra. Then, its Cu(II), Ni(II), Co(II), Mn(II) and VO(IV) complexes were synthesized by the template effect of 2-Hydroxy acetophenone, 4-chloro-2,6-diaminopyrimidine and (CH3COO)2Cu.H2O, (CH3COO)2Ni.4H2O, (CH3COO)2Co.4H2O, (CH3COO)2Mn.4H2O and VOSO4.5H2O respectively. The structure of the newly prepared complexes were identified by elemetal analyses, molar conductance, infrared, electronic, magnetic susceptibility and electrochemical studies. The bonding sites are the azomethine nitrogen atoms and phenolic oxygen atoms.The schiff base ligand and its metal complexes were tested against four pathogenic bacteria (Staphylococcus aureus, Bacillus substilis) as Gram-positive bacteria, and (Escherichia coli, Klebsiella pneumonia) as Gram-negative bacteria. All the metal complexes exhibit higher antibacterial activity than the free ligand. Cobalt(II) complexes have higher bacterial activity and Nickel(II) than the other complexes.