AUTHOR=Dai Ali , Zheng Zhiguo , Yu Lijiao , Huang Yuanqin , Wu Jian 

TITLE=1,3,4-Oxadiazole Contained Sesquiterpene Derivatives: Synthesis and Microbiocidal Activity for Plant Disease

JOURNAL=Frontiers in Chemistry

VOLUME=10

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.854274

DOI=10.3389/fchem.2022.854274

ISSN=2296-2646

ABSTRACT=<p>A series of 1,3,4-oxadiazole contained sesquiterpene derivatives were synthesized, and the activity of the target compounds against <italic>Xanthomonas oryzae</italic> pv. <italic>oryzae</italic> (<italic>Xoo</italic>)<italic>, Xanthomonas axonopodis</italic> pv. <italic>citri</italic> (<italic>Xac</italic>)<italic>,</italic> and tobacco mosaic virus (TMV) were evaluated. The biological activity results showed that the EC<sub>50</sub> values of compounds <bold>H4</bold>, <bold>H8</bold>, <bold>H11</bold>, <bold>H12</bold>, <bold>H14</bold>, <bold>H16</bold>, and <bold>H19</bold> for <italic>Xac</italic> inhibitory activity were 33.3, 42.7, 56.1, 74.5, 37.8, 43.8, and 38.4 μg/ml, respectively. Compounds <bold>H4</bold>, <bold>H8</bold>, <bold>H15</bold>, <bold>H19</bold>, <bold>H22</bold>, and <bold>H23</bold> had inhibitory effects on <italic>Xoo</italic>, with EC<sub>50</sub> values of 51.0, 43.3, 43.4, 50.5, 74.6, and 51.4 μg/ml, respectively. In particular, the curative and protective activities of compound <bold>H8</bold> against <italic>Xoo in vivo</italic> were 51.9 and 49.3%, respectively. In addition, the EC<sub>50</sub> values of the inactivation activity of compounds <bold>H4</bold>, <bold>H5</bold>, <bold>H9</bold>, <bold>H10</bold>, and <bold>H16</bold> against TMV were 69.6, 58.9, 69.4, 43.9, and 60.5 μg/ml, respectively. The results of molecular docking indicated that compound <bold>H10</bold> exhibited a strong affinity for TMV-coat protein, with a binding energy of −8.88 kcal/mol. It may inhibit the self-assembly and replication of TMV particles and have an anti-TMV effect, which supports its potential usefulness as an antiviral agent.</p>