2-(4-Toluenesulphonyloxy phenyl)-3,1-benzoxazine-4-one 2 was prepared and reacted with some nitrogen nucleophiles, e.g., ammonia, o-phenylendiamine, some heterocyclic amines, hydrazine hydrate and hydroxylamine hydrochloride and sulphur nucleophile, e.g., phosphorous pentasulphide. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. All new prepared compounds were subjected to antimicrobial activity evaluation where compounds, 8, 9, 10 and 18 exhibited good activities against Bacillus Thuringenesis and 5, 10, 11, 14, 15, 17 and 18 exhibited good activities against Klebseilla Pneumonia. On the other hand, the results for antifungal activities revealed that, compounds 5, 6, 7, 16 and 17 exhibited good activities against Trichoderma Herzianum and Trichoderma Virdi.