Design, Synthesis and Antifungal Activity of Novel 1,4-Pentadiene-3-one Containing Quinazolinone
Twenty 1,4-pentadiene-3-one derivatives containing quinazolinone (<b>W1</b>–<b>W20</b>) were designed and synthesized. The bioactivity test results showed that some compounds had antifungal activities in vitro. <b>W12</b> showed excellent bioactivity against <i...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-01-01
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| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/24/3/2599 |
| Summary: | Twenty 1,4-pentadiene-3-one derivatives containing quinazolinone (<b>W1</b>–<b>W20</b>) were designed and synthesized. The bioactivity test results showed that some compounds had antifungal activities in vitro. <b>W12</b> showed excellent bioactivity against <i>Sclerotinia sclerotiorum</i> (<i>S. sclerotiorum</i>) and <i>Phomopsis</i> sp., with EC<sub>50</sub> values of 0.70 and 3.84 μg/mL, which are higher than those of the control drug azoxystrobin at 8.15 and 17.25 μg/mL. In vivo activity tests were carried out on oilseed rape and kiwifruit. The protective effect of <b>W12</b> on oilseed rape infected with <i>S. sclerotiorum</i> (91.7 and 87.3%) was better than that of azoxystrobin (90.2 and 79.8%) at 100 and 50 μg/mL, respectively, and the protective effect on kiwifruit infected with <i>Phomopsis</i> sp. (96.2%) was better than that of azoxystrobin (94.6%) at 200 μg/mL. Scanning electron microscopy results showed the hyphae of <i>S. sclerotiorum</i> treated with compound <b>W12</b> abnormally collapsed and shriveled, inhibiting the growth of mycelium and, thus, laying the inhibiting effect on <i>S. sclerotiorum</i>. The results of the mechanism research showed that the action of <b>W12</b> changed the mycelial morphology of <i>S. sclerotiorum</i>, affected the permeability of cells, increased the leakage of cytoplasm and allowed the cell membrane to break down. This study shows that 1,4-pentadiene-3-one derivatives containing quinazolinone have good effects on plant fungi and the potential for becoming new fungicides. |
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| ISSN: | 1661-6596 1422-0067 |