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The scope of the present work is to study the biodegradability behavior of several novel heterocyclic poly(ether urethanes) when their hard segments are subjected to exposure to the Alternaria tenuissima fungus. The heterocyclic poly(ether urethanes) were chain-extended with various pyridine derivatives that had different functional groups placed in different positions on the pyridine rings. Different ratios of the reactive components were also used. The measurements obtained by the use of the attenuated total reflectance-Fourier transform infrared spectroscopy revealed the different structural changes that occurred after exposure to fungi. The degradation process was analyzed through measurement of the mechanical properties and surface morphology evolution by scanning electron microscopy. The obtained results show that the nature and design of the functional groups on the pyridine ring determine the strength of the cohesion linkages that in turn influence different degradation behaviors under exposure to fungi. V C 2017Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46096.