Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide Fragments
Plant diseases caused by pathogenic fungi or oomycetes seriously affect crop growth and the quality and yield of products. A series of novel 1,2,4-triazole derivatives containing carboxamide fragments based on amide fragments widely used in fungicides and the commercialized mefentrifluconazole were...
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| Format: | Article |
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MDPI AG
2024-02-01
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| Series: | Journal of Fungi |
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| Online Access: | https://www.mdpi.com/2309-608X/10/2/160 |
| _version_ | 1797297768697430016 |
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| author | Jiali Wang Haoran Shi Aidang Lu |
| author_facet | Jiali Wang Haoran Shi Aidang Lu |
| author_sort | Jiali Wang |
| collection | DOAJ |
| description | Plant diseases caused by pathogenic fungi or oomycetes seriously affect crop growth and the quality and yield of products. A series of novel 1,2,4-triazole derivatives containing carboxamide fragments based on amide fragments widely used in fungicides and the commercialized mefentrifluconazole were designed and synthesized. Their antifungal activities were evaluated against seven kinds of phytopathogenic fungi/oomycete. Results showed that most compounds had similar or better antifungal activities compared to mefentrifluconazole’s inhibitory activity against <i>Physalospora piricola</i>, especially compound <b>6h</b> (92%), which possessed outstanding activity. Compound <b>6h</b> (EC<sub>50</sub> = 13.095 μg/mL) showed a better effect than that of mefentrifluconazole (EC<sub>50</sub> = 39.516 μg/mL). Compound <b>5j</b> (90%) displayed outstanding anti-oomycete activity against <i>Phytophthora capsici</i>, with an EC<sub>50</sub> value of 17.362 μg/mL, far superior to that of mefentrifluconazole (EC<sub>50</sub> = 75.433 μg/mL). The result of molecular docking showed that compounds <b>5j</b> and <b>6h</b> possessed a stronger affinity for 14α-demethylase (CYP51). This study provides a new approach to expanding the fungicidal spectrum of 1,2,4-triazole derivatives. |
| first_indexed | 2024-03-07T22:26:10Z |
| format | Article |
| id | doaj.art-db5f1b4c93af4093a6b943bc2d54dd8f |
| institution | Directory Open Access Journal |
| issn | 2309-608X |
| language | English |
| last_indexed | 2024-03-07T22:26:10Z |
| publishDate | 2024-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Journal of Fungi |
| spelling | doaj.art-db5f1b4c93af4093a6b943bc2d54dd8f2024-02-23T15:23:36ZengMDPI AGJournal of Fungi2309-608X2024-02-0110216010.3390/jof10020160Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide FragmentsJiali Wang0Haoran Shi1Aidang Lu2School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300401, ChinaSchool of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300401, ChinaSchool of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300401, ChinaPlant diseases caused by pathogenic fungi or oomycetes seriously affect crop growth and the quality and yield of products. A series of novel 1,2,4-triazole derivatives containing carboxamide fragments based on amide fragments widely used in fungicides and the commercialized mefentrifluconazole were designed and synthesized. Their antifungal activities were evaluated against seven kinds of phytopathogenic fungi/oomycete. Results showed that most compounds had similar or better antifungal activities compared to mefentrifluconazole’s inhibitory activity against <i>Physalospora piricola</i>, especially compound <b>6h</b> (92%), which possessed outstanding activity. Compound <b>6h</b> (EC<sub>50</sub> = 13.095 μg/mL) showed a better effect than that of mefentrifluconazole (EC<sub>50</sub> = 39.516 μg/mL). Compound <b>5j</b> (90%) displayed outstanding anti-oomycete activity against <i>Phytophthora capsici</i>, with an EC<sub>50</sub> value of 17.362 μg/mL, far superior to that of mefentrifluconazole (EC<sub>50</sub> = 75.433 μg/mL). The result of molecular docking showed that compounds <b>5j</b> and <b>6h</b> possessed a stronger affinity for 14α-demethylase (CYP51). This study provides a new approach to expanding the fungicidal spectrum of 1,2,4-triazole derivatives.https://www.mdpi.com/2309-608X/10/2/1601,2,4-triazole derivativescarboxamide fragmentsfungicidal activity<i>Physalospora piricola</i><i>Phytophthora capsici</i>molecular docking |
| spellingShingle | Jiali Wang Haoran Shi Aidang Lu Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide Fragments Journal of Fungi 1,2,4-triazole derivatives carboxamide fragments fungicidal activity <i>Physalospora piricola</i> <i>Phytophthora capsici</i> molecular docking |
| title | Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide Fragments |
| title_full | Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide Fragments |
| title_fullStr | Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide Fragments |
| title_full_unstemmed | Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide Fragments |
| title_short | Design, Synthesis, and Antifungal/Anti-Oomycete Activities of Novel 1,2,4-Triazole Derivatives Containing Carboxamide Fragments |
| title_sort | design synthesis and antifungal anti oomycete activities of novel 1 2 4 triazole derivatives containing carboxamide fragments |
| topic | 1,2,4-triazole derivatives carboxamide fragments fungicidal activity <i>Physalospora piricola</i> <i>Phytophthora capsici</i> molecular docking |
| url | https://www.mdpi.com/2309-608X/10/2/160 |
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