Fifteen novel biologically active macrocycles have been synthesized by condensing orthophthalaldehyde with different primary amines and characterized by elemental analysis, IR, 1H, 13C NMR and mass spectral analysis. Four macrocycles were found to have potent antibacterial activity against Gram +ve and Gram –ve bacteria when compared to the two existing antibacterial drugs viz. streptomycin and ampicillin. These compounds also tested for fungicidal activity.