| Summary: | A series of novel indole Schiff base derivatives (<b>2a</b>–<b>2t</b>) containing a 1,3,4-thiadiazole scaffold modified with a thioether group were synthesized, and their structures were confirmed using FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HR-MS. In addition, the antifungal activity of synthesized indole derivatives was investigated against <i>Fusarium graminearum</i> (<i>F. graminearum</i>), <i>Fusarium oxysporum</i> (<i>F. oxysporum)</i>, <i>Fusarium</i><i>moniliforme</i> (<i>F.</i><i>moniliforme</i>), <i>Curvularia lunata (C. lunata</i>), and <i>Phytophthora parasitica</i> var. <i>nicotiana</i> (<i>P. p.</i> var. <i>nicotianae</i>) using the mycelium growth rate method. Among the synthesized indole derivatives, compound <b>2j</b> showed the highest inhibition rates of 100%, 95.7%, 89%, and 76.5% at a concentration of 500 μg/mL against <i>F. graminearum</i>, <i>F. oxysporum</i>, <i>F.</i><i>moniliforme</i>, and <i>P. p.</i> var. <i>nicotianae</i>, respectively. Similarly, compounds <b>2j</b> and <b>2q</b> exhibited higher inhibition rates of 81.9% and 83.7% at a concentration of 500 μg/mL against <i>C. lunata</i>. In addition, compound <b>2j</b> has been recognized as a potential compound for further investigation in the field of fungicides.
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