Acetic acid functionalized poly(4-vinylpyridinium) bromide (APVPB), as a new and heterogeneous catalyst, was designed and successfully tested on the synthesis of 2-aminospiro[indoline-3,4'pyran]-2one and spiro[indeno[1,2-1Aquinoxaline-11,4-pyran]-2'-amine derivatives. Also, infrared spectroscopy (FT-IR), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), scanning electron microscope (SEM), X-ray diffraction analysis (XRD) and energy dispersive X-ray analysis (EDX) of the catalyst has been studied in the presented work. The prepared spiro-pyrans were solved in DMSO and subjected to antioxidant activity screening by DPPH free radical scavenging assay and antifungal activity against Fusarium oxysporum. Results showed that the synthesized spiro-pyran possess strong antioxidant activity (IC50; 0.161 +/- 0.009 to 1.509 +/- 0.007 mg/ml) and also good inhibition activity against Fusarium oxysporum (65.8 +/- 1.4% to 88.3 +/- 2.2% at 500 ppm concentration and 89.2 3.2% to 100 0.0% at 1000 ppm concentration). For their biological activities, the prepared spiro-pyran compounds may be suggested to apply as alternative systems in medicine and agriculture. (C) 2016 Elsevier B.V. All rights reserved.