The environmentally benign catalyst and solvent-free synthesis of ketonitrones may not always be accomplished by simple condensation reactions. The occasional reports of green synthetic routes toward these compounds have been reported. The key features of this 1,3-dipolar cycloaddition reactions of N-[4-(-carboxycyclohexylmethyl)]maleimide with substituted isatin ketonitrone under microwave conditions resulted in the green synthesis of series of novel fluoro-substituted spiro[oxindole-isoxazolidine] derivatives in high yields, improved purity and short reaction times. All the synthesized compounds have been identified as potent in vitro antimicrobial agents. These results promoted the greener route to synthesize spiro[oxindole-isoxazolidine] derivatives with immense pharmacological importance in eco-friendly manner.