The synthesis of isatin hydrazide have been done in high yields at room temperature starting from indoledione (Isatin) and hydrazine hydrate. A one –pot three component Kabachnik Fields reaction was used to synthesize mono and di-α- aminophosphonate system using mono and dialdehydes containing isatin hydrazide and triethyl phosphite in methylene chloride⁄ DMF mixture using Cupper triflate as Lewis acid catalyst. The structure of those aminophosphonate derivatives have been confirmed by elemental analysis and by FT-IR, NMR spectral analysis. Mono- α-aminophosphonates azo dyes have additionally been efficaciously applied to make printing pastes for polyester fabric. The color strength and fastness properties of the printed fabrics- to washing, perspiration, and light- demonstrated moderate to excellent results. Those derivatives as well as their printed samples showed high antibacterial activities against Staphylococcus aureus (Gram +ve) and Pseudomonas auroginosa (Gram -ve) and Candida albicans (yeast) at low concentrations (2.5–10 mg /mL).