Synthesis and antibacterial activity of naringenin derivatives containing selenocyanate moiety

To control plant pathogen infections, we synthesized naringenin derivatives bearing selenocyanate moieties and assayed their antibacterial activity against <i>Xanthomonas axonopodis</i> pv<i>. citri</i>, <i>Xanthomonas oryzae</i> pv<i>. oryzae</i>, and <i>Xanthomonas oryzae</i> pv<i>. oryzicola via</i> the microbroth dilution method. Structures were confirmed by ¹H NMR, ¹³C NMR and HRMS. Compounds <b>4a</b> and <b>4b</b> featuring ether substitution at the 7-hydroxyl of naringenin showed potent activity against <i>X. axonopodis</i> pv. <i>citri</i> (EC₅₀: 0.33-0.38 μg/ml) and <i>X. oryzae</i> pv. <i>Oryzicola</i> (EC₅₀: 0.36-0.75 μg/ml), while <b>5b</b> and <b>8c</b> outperformed chlorothalonil against <i>X. oryzae</i> pv. <i>Oryzae</i> (EC₅₀: 1.05-1.42 μg/ml). This study provides valuable insights for developing novel plant disease control agents.