Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety
A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-...
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MDPI AG
2020-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/24/5852 |
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| author | Hui Bai Xuelian Liu Pengfei Chenzhang Yumei Xiao Bin Fu Zhaohai Qin |
| author_facet | Hui Bai Xuelian Liu Pengfei Chenzhang Yumei Xiao Bin Fu Zhaohai Qin |
| author_sort | Hui Bai |
| collection | DOAJ |
| description | A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (<b>5a18</b>) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (<b>5a4</b>) exhibited a broad-spectrum antifungal activities with the EC<sub>50</sub> values of 1.59, 0.46, 0.27 and 11.39 mg/L against <i>S. sclerotiorum</i>, <i>P. infestans</i>, <i>R. solani</i> and <i>B. cinerea</i>, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (<b>5b2</b>) provided the lowest EC<sub>50</sub> value of 0.12 mg/L against <i>S. sclerotiorum</i>, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds <b>5a4</b> and <b>5b2</b> with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides. |
| first_indexed | 2024-03-10T14:09:51Z |
| format | Article |
| id | doaj.art-8900e963f2df41b19b9021f6525c66cc |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T14:09:51Z |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-8900e963f2df41b19b9021f6525c66cc2023-11-21T00:19:08ZengMDPI AGMolecules1420-30492020-12-012524585210.3390/molecules25245852Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl MoietyHui Bai0Xuelian Liu1Pengfei Chenzhang2Yumei Xiao3Bin Fu4Zhaohai Qin5Department of Chemistry, College of Science, China Agricultural University, Beijing 100193, ChinaDepartment of Chemistry, College of Science, China Agricultural University, Beijing 100193, ChinaDepartment of Chemistry, College of Science, China Agricultural University, Beijing 100193, ChinaDepartment of Chemistry, College of Science, China Agricultural University, Beijing 100193, ChinaDepartment of Chemistry, College of Science, China Agricultural University, Beijing 100193, ChinaDepartment of Chemistry, College of Science, China Agricultural University, Beijing 100193, ChinaA series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (<b>5a18</b>) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (<b>5a4</b>) exhibited a broad-spectrum antifungal activities with the EC<sub>50</sub> values of 1.59, 0.46, 0.27 and 11.39 mg/L against <i>S. sclerotiorum</i>, <i>P. infestans</i>, <i>R. solani</i> and <i>B. cinerea</i>, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (<b>5b2</b>) provided the lowest EC<sub>50</sub> value of 0.12 mg/L against <i>S. sclerotiorum</i>, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds <b>5a4</b> and <b>5b2</b> with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.https://www.mdpi.com/1420-3049/25/24/58521,2,4-triazoleoxime etherphenoxy pyridinylfungicidal activityCYP51 |
| spellingShingle | Hui Bai Xuelian Liu Pengfei Chenzhang Yumei Xiao Bin Fu Zhaohai Qin Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety Molecules 1,2,4-triazole oxime ether phenoxy pyridinyl fungicidal activity CYP51 |
| title | Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety |
| title_full | Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety |
| title_fullStr | Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety |
| title_full_unstemmed | Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety |
| title_short | Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety |
| title_sort | design synthesis and fungicidal activity of new 1 2 4 triazole derivatives containing oxime ether and phenoxyl pyridinyl moiety |
| topic | 1,2,4-triazole oxime ether phenoxy pyridinyl fungicidal activity CYP51 |
| url | https://www.mdpi.com/1420-3049/25/24/5852 |
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