Nucleophilic substitution and 1,3-dipolar cycloaddition reactions were used to synthesize 3,6-disubstituted derivatives of simm-tetrazine containing azolyl, aminoalkyl, and oxyalkyl fragments. The antibacterial activity of the resulting compounds was studied using the obligate pathogen Neisseria gonorrhoeae and opportunistic pathogenic microorganisms, while antifungal activity was assessed using anthropo- and zooanthropophilic dermatophytes.