The effect of 18 newly synthesized esters and amides of 3-(5-nitro-2-furyl)acrylic acid on bacteria (Escherichia coli, Staphylococcus aureus), yeasts (Saccharomyces cerevisiae, Candida albicans), molds (Aspergillus niger, Penicillium cyclopium, Rhizopus oryzae) and algae (Chlorella pyrenoidosa, Euglena gracilis, Scenedesmus obliquus) was investigated. The MIC values revealed antimycotic, antialgal and antibacterial activity of the studied derivatives. The antimycotic activity was found to decrease with increasing the length of the alkyl chain of esters and after introduction of amino nitrogen into the furylethylene backbone. The inhibitory effect on growth is caused by blocking bioenergetic processes, glycolysis in particular.

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The dependence has been found of the quantum yield Φ of photochemical rearrangement of the title compounds (where R means ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, 2-furyl, 2-thienyl) on the exo(I) or endo (II) arrangement of the R substituent. The endo derivatives exhibit higher Φ values (0.020-0.041) than the exo derivatives (0.007-0.019). The photochemical rearrangement gives the derivatives of 2-R-6-phenyl-7-formyl-2,4,5,8-tetrahydro-1,3-dioxa-5-azocine as the single products in good yields. The 2-furyl derivative gives polymeric products. The title compounds have been prepared by 1,3-dipolar cycloaddition of benzenenitriloxide to the respective substituted 1,3-dioxep-5-enes.

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