Novel Schiff base ligand 3-chloro-4-methyl-N-[(1E)-1-phenylethylidene]aniline have been synthesized by the condensation of 1-phenylethanone with 3-chloro-4-methylaniline.Transition metal complexes of Mn(II), Fe(II), Co(II) and Ni(II) have also been synthesized. The ligand and its metal complexes were characterized based on mass spectral data, IR, 1HNMR and 13CNMR spectroscopy. The spectral data of the metal complexes were interpreted on the basis of comparison with that of the free ligand. The analysis showed that the ligand coordinated to the metal ion through the azomethine nitrogen, the chloride and two aqua molecules. An octahedral geometry have been suggested for the metal complexes. The compounds were screened against Aspergillus niger Macrophomina phaseolina, Fusarium oxysporum and Alternaria alternatea. Their potency have been discussed. It has been found that all the complexes are active and showed higher activity than the free ligand. Metal chelation affected the bioactive behavior of the organic ligand.