In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors
A series of novel 3-phenoxy-4-(3-trifluoromethylphenyl)pyridazines <b>2</b>–<b>5</b> were designed, based on the structure of our previous lead compound <b>1</b> through the in silico structure-guided optimization approach. The results showed that some of these ne...
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MDPI AG
2021-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/22/6979 |
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| author | Lijun Yang Dawei Wang Dejun Ma Di Zhang Nuo Zhou Jing Wang Han Xu Zhen Xi |
| author_facet | Lijun Yang Dawei Wang Dejun Ma Di Zhang Nuo Zhou Jing Wang Han Xu Zhen Xi |
| author_sort | Lijun Yang |
| collection | DOAJ |
| description | A series of novel 3-phenoxy-4-(3-trifluoromethylphenyl)pyridazines <b>2</b>–<b>5</b> were designed, based on the structure of our previous lead compound <b>1</b> through the in silico structure-guided optimization approach. The results showed that some of these new compounds showed a good herbicidal activity at the rate of 750 g ai/ha by both pre- and post-emergence applications, especially compound <b>2a</b>, which displayed a comparable pre-emergence herbicidal activity to diflufenican at 300–750 g ai/ha, and a higher post-emergence herbicidal activity than diflufenican at the rates of 300–750 g ai/ha. Additionally, <b>2a</b> was safe to wheat by both pre- and post-emergence applications at 300 g ai/ha, showing the compound’s potential for weed control in wheat fields. Our molecular simulation studies revealed the important factors involved in the interaction between <b>2a</b> and <i>Synechococcus</i> PDS. This work provided a lead compound for weed control in wheat fields. |
| first_indexed | 2024-03-10T05:13:39Z |
| format | Article |
| id | doaj.art-800a4978bc0b481ab5f2eb95f431b2ac |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T05:13:39Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-800a4978bc0b481ab5f2eb95f431b2ac2023-11-23T00:36:43ZengMDPI AGMolecules1420-30492021-11-012622697910.3390/molecules26226979In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase InhibitorsLijun Yang0Dawei Wang1Dejun Ma2Di Zhang3Nuo Zhou4Jing Wang5Han Xu6Zhen Xi7National Pesticide Engineering Research Center, Department of Chemical Biology, State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaNational Pesticide Engineering Research Center, Department of Chemical Biology, State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaNational Pesticide Engineering Research Center, Department of Chemical Biology, State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaNational Pesticide Engineering Research Center, Department of Chemical Biology, State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaNational Pesticide Engineering Research Center, Department of Chemical Biology, State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaState Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, No. 38, Xueyuan Road, Beijing 100191, ChinaNational Pesticide Engineering Research Center, Department of Chemical Biology, State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaNational Pesticide Engineering Research Center, Department of Chemical Biology, State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, ChinaA series of novel 3-phenoxy-4-(3-trifluoromethylphenyl)pyridazines <b>2</b>–<b>5</b> were designed, based on the structure of our previous lead compound <b>1</b> through the in silico structure-guided optimization approach. The results showed that some of these new compounds showed a good herbicidal activity at the rate of 750 g ai/ha by both pre- and post-emergence applications, especially compound <b>2a</b>, which displayed a comparable pre-emergence herbicidal activity to diflufenican at 300–750 g ai/ha, and a higher post-emergence herbicidal activity than diflufenican at the rates of 300–750 g ai/ha. Additionally, <b>2a</b> was safe to wheat by both pre- and post-emergence applications at 300 g ai/ha, showing the compound’s potential for weed control in wheat fields. Our molecular simulation studies revealed the important factors involved in the interaction between <b>2a</b> and <i>Synechococcus</i> PDS. This work provided a lead compound for weed control in wheat fields.https://www.mdpi.com/1420-3049/26/22/6979herbicidal activitymolecular designphytoene desaturasepyridazine |
| spellingShingle | Lijun Yang Dawei Wang Dejun Ma Di Zhang Nuo Zhou Jing Wang Han Xu Zhen Xi In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors Molecules herbicidal activity molecular design phytoene desaturase pyridazine |
| title | In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors |
| title_full | In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors |
| title_fullStr | In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors |
| title_full_unstemmed | In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors |
| title_short | In Silico Structure-Guided Optimization and Molecular Simulation Studies of 3-Phenoxy-4-(3-trifluoromethylphenyl)pyridazines as Potent Phytoene Desaturase Inhibitors |
| title_sort | in silico structure guided optimization and molecular simulation studies of 3 phenoxy 4 3 trifluoromethylphenyl pyridazines as potent phytoene desaturase inhibitors |
| topic | herbicidal activity molecular design phytoene desaturase pyridazine |
| url | https://www.mdpi.com/1420-3049/26/22/6979 |
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