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Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs
We investigated the synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. Optically active cinmethylin could be obtained in seven steps with the Sharpless asymmetric dihydroxylation of α-terpinene. The synthesized cinmethylin and i...
| Autores principales: | , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Pesticide Science Society of Japan
2023
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9978247/ https://www.ncbi.nlm.nih.gov/pubmed/36874636 http://dx.doi.org/10.1584/jpestics.D22-051 |
| _version_ | 1784899477095579648 |
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| author | Ogawa, Narihito Toyoshima, Shoya Sekikawa, Shinya Ishijima, Masahiro Katagiri, Kyosuke Uematsu, Chihiro Hirano, Tatsuya Ootaka, Akihito Suzuki, Jun |
| author_facet | Ogawa, Narihito Toyoshima, Shoya Sekikawa, Shinya Ishijima, Masahiro Katagiri, Kyosuke Uematsu, Chihiro Hirano, Tatsuya Ootaka, Akihito Suzuki, Jun |
| author_sort | Ogawa, Narihito |
| collection | PubMed |
| description | We investigated the synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. Optically active cinmethylin could be obtained in seven steps with the Sharpless asymmetric dihydroxylation of α-terpinene. The synthesized cinmethylin and its enantiomer showed similar herbicidal activity, which was independent of the stereochemistry. Next, we synthesized cinmethylin analogs with various substituents at the C3 position. We found that analogs with methylene, oxime, ketone, or methyl groups at the C3 position show excellent herbicidal activity. |
| format | Online Article Text |
| id | pubmed-9978247 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2023 |
| publisher | Pesticide Science Society of Japan |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-99782472023-03-03 Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs Ogawa, Narihito Toyoshima, Shoya Sekikawa, Shinya Ishijima, Masahiro Katagiri, Kyosuke Uematsu, Chihiro Hirano, Tatsuya Ootaka, Akihito Suzuki, Jun J Pestic Sci Regular Article We investigated the synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs. Optically active cinmethylin could be obtained in seven steps with the Sharpless asymmetric dihydroxylation of α-terpinene. The synthesized cinmethylin and its enantiomer showed similar herbicidal activity, which was independent of the stereochemistry. Next, we synthesized cinmethylin analogs with various substituents at the C3 position. We found that analogs with methylene, oxime, ketone, or methyl groups at the C3 position show excellent herbicidal activity. Pesticide Science Society of Japan 2023-02-20 /pmc/articles/PMC9978247/ /pubmed/36874636 http://dx.doi.org/10.1584/jpestics.D22-051 Text en © 2023 Pesticide Science Society of Japan https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) License. |
| spellingShingle | Regular Article Ogawa, Narihito Toyoshima, Shoya Sekikawa, Shinya Ishijima, Masahiro Katagiri, Kyosuke Uematsu, Chihiro Hirano, Tatsuya Ootaka, Akihito Suzuki, Jun Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs |
| title | Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs |
| title_full | Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs |
| title_fullStr | Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs |
| title_full_unstemmed | Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs |
| title_short | Synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and C3-substituted cinmethylin analogs |
| title_sort | synthesis and herbicidal activity of optically active cinmethylin, its enantiomer, and c3-substituted cinmethylin analogs |
| topic | Regular Article |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9978247/ https://www.ncbi.nlm.nih.gov/pubmed/36874636 http://dx.doi.org/10.1584/jpestics.D22-051 |
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