Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-Alkenylthiopyrimidine
A series of novel phenyl methoxyacrylate derivatives containing a 2-alkenylthiopyrimidine substructure were designed, synthesized, and evaluated in terms of acaricidal activity. The structures of the title compounds were identified by <sup>1</sup>H NMR, <sup>13</sup>C NMR and...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/15/3379 |
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| author | Shulin Hao Zengfei Cai Yangyang Cao Xiaohua Du |
| author_facet | Shulin Hao Zengfei Cai Yangyang Cao Xiaohua Du |
| author_sort | Shulin Hao |
| collection | DOAJ |
| description | A series of novel phenyl methoxyacrylate derivatives containing a 2-alkenylthiopyrimidine substructure were designed, synthesized, and evaluated in terms of acaricidal activity. The structures of the title compounds were identified by <sup>1</sup>H NMR, <sup>13</sup>C NMR and high-resolution mass spectra (HRMS). Compound (<i>E</i>)-methyl 2-(2-((2-(3,3-dichloroallylthio)-6-(trifluoromethyl)pyrimidin-4-yloxy)methyl)phenyl)-3-methoxyacr-ylate (<b>4j</b>) exhibited significant acaricidal activity against <i>Tetranychus cinnabarinus</i> (<i>T. cinnabarinus</i>) in greenhouse tests possessing nearly twice the larvicidal and ovicidal activity compared to fluacrypyrim. Furthermore, the results of the field trials demonstrated that compound <b>4j</b> could effectively control <i>Panonychuscitri</i> with long-lasting persistence and rapid action. The toxicology data in terms of LD<sub>50</sub> value confirmed that compound <b>4j</b> has a relatively low acute toxicity to mammals, birds, and honeybees. |
| first_indexed | 2024-03-10T18:13:32Z |
| format | Article |
| id | doaj.art-ef4e9a29971b4a258f874b58d30af688 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T18:13:32Z |
| publishDate | 2020-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ef4e9a29971b4a258f874b58d30af6882023-11-20T07:57:10ZengMDPI AGMolecules1420-30492020-07-012515337910.3390/molecules25153379Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-AlkenylthiopyrimidineShulin Hao0Zengfei Cai1Yangyang Cao2Xiaohua Du3Catalytic Hydrogenation Research Center, Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Zhejiang Green Pesticide Collaborative Innovation Center, Zhejiang University of Technology, Hangzhou 310014, ChinaCatalytic Hydrogenation Research Center, Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Zhejiang Green Pesticide Collaborative Innovation Center, Zhejiang University of Technology, Hangzhou 310014, ChinaCatalytic Hydrogenation Research Center, Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Zhejiang Green Pesticide Collaborative Innovation Center, Zhejiang University of Technology, Hangzhou 310014, ChinaCatalytic Hydrogenation Research Center, Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Zhejiang Green Pesticide Collaborative Innovation Center, Zhejiang University of Technology, Hangzhou 310014, ChinaA series of novel phenyl methoxyacrylate derivatives containing a 2-alkenylthiopyrimidine substructure were designed, synthesized, and evaluated in terms of acaricidal activity. The structures of the title compounds were identified by <sup>1</sup>H NMR, <sup>13</sup>C NMR and high-resolution mass spectra (HRMS). Compound (<i>E</i>)-methyl 2-(2-((2-(3,3-dichloroallylthio)-6-(trifluoromethyl)pyrimidin-4-yloxy)methyl)phenyl)-3-methoxyacr-ylate (<b>4j</b>) exhibited significant acaricidal activity against <i>Tetranychus cinnabarinus</i> (<i>T. cinnabarinus</i>) in greenhouse tests possessing nearly twice the larvicidal and ovicidal activity compared to fluacrypyrim. Furthermore, the results of the field trials demonstrated that compound <b>4j</b> could effectively control <i>Panonychuscitri</i> with long-lasting persistence and rapid action. The toxicology data in terms of LD<sub>50</sub> value confirmed that compound <b>4j</b> has a relatively low acute toxicity to mammals, birds, and honeybees.https://www.mdpi.com/1420-3049/25/15/3379phenyl methoxyacrylatesthioethersynthesisacaricidal activitystructure activity relationships |
| spellingShingle | Shulin Hao Zengfei Cai Yangyang Cao Xiaohua Du Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-Alkenylthiopyrimidine Molecules phenyl methoxyacrylates thioether synthesis acaricidal activity structure activity relationships |
| title | Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-Alkenylthiopyrimidine |
| title_full | Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-Alkenylthiopyrimidine |
| title_fullStr | Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-Alkenylthiopyrimidine |
| title_full_unstemmed | Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-Alkenylthiopyrimidine |
| title_short | Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-Alkenylthiopyrimidine |
| title_sort | design synthesis and acaricidal activity of phenyl methoxyacrylates containing 2 alkenylthiopyrimidine |
| topic | phenyl methoxyacrylates thioether synthesis acaricidal activity structure activity relationships |
| url | https://www.mdpi.com/1420-3049/25/15/3379 |
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