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Triazenes are versatile and belong to a group of alkylating agents with interesting physicochemical properties and proven biological activities. This study describes the synthesis, molecular and crystalline structure, biological activity evaluation, and antifungal and antimicrobial potentials of 1,3-<jats:italic>bis<\/jats:italic>(X-methoxy-Y-nitrophenyl)triazenes [X\u2009=\u20092 and 5; Y\u2009=\u20094 and 5]. The antimicrobial and antifungal activities of the compounds were tested by evaluating the sensitivity of bacteria (American Type Culture Collection, ATCC) and clinical isolates to their solutions using standardized microbiological assays, cytotoxicity evaluation, and ecotoxicity tests. The antimicrobial potentials of triazenes were determined according to their minimum inhibitory concentrations (MICs); these compounds were active against gram-positive and gram-negative bacteria, with low MIC values. The most surprising result was obtained for <jats:bold>T3<\/jats:bold> having the effective MIC of 9.937\u00a0\u00b5g\/mL and antifungal activity against <jats:italic>Candida albicans<\/jats:italic> ATCC 90028, <jats:italic>C. parapsilosis<\/jats:italic> ATCC 22019, and <jats:italic>C. tropicallis<\/jats:italic> IC. To the best of our knowledge, this study is the first to report promising activities of triazene compounds against yeast and filamentous fungi. 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