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Synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in Arabidopsis seedlings
Twenty-seven analogues of pyrazole derivatives were synthesized and subjected to structure–activity relationship studies on inducing the triple response in Arabidopsis seedlings. We found that 3,4-Dichloro-N-methyl-N-[(1-allyl-3,5-dimethyl-1H-pyrazol-4-yl)methyl]benzenesulfonamide (C26) exhibits pot...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Pesticide Science Society of Japan
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6861426/ https://www.ncbi.nlm.nih.gov/pubmed/31777442 http://dx.doi.org/10.1584/jpestics.D19-037 |
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author | Oh, Keimei Hoshi, Tomoki |
author_facet | Oh, Keimei Hoshi, Tomoki |
author_sort | Oh, Keimei |
collection | PubMed |
description | Twenty-seven analogues of pyrazole derivatives were synthesized and subjected to structure–activity relationship studies on inducing the triple response in Arabidopsis seedlings. We found that 3,4-Dichloro-N-methyl-N-[(1-allyl-3,5-dimethyl-1H-pyrazol-4-yl)methyl]benzenesulfonamide (C26) exhibits potent activity on inducing the triple response in Arabidopsis seedlings. C26 (10 µM) induced an exaggerated apical hook in Arabidopsis seedlings. The curvature of the hook of the Arabidopsis seedlings was found to be 300±23 degrees, while ethephon (10 µM), a prodrug of ethylene, and a non-chemically treated control were found to be 128±19 and 58±16 degrees, respectively. C26 also exhibited potent activity on reducing stem elongation. The hypocotyl length of Arabidopsis seedlings treated with C26 (10 µM) was found to be 0.25±0.02 cm, while those of ethephon-treated (10 µM) and treated controls were found to be 0.69±0.06 and 1.15±0.01 cm, respectively. C26 displayed potency inhibiting the root growth of Arabidopsis seedlings similar to that of ethephon. |
format | Online Article Text |
id | pubmed-6861426 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Pesticide Science Society of Japan |
record_format | MEDLINE/PubMed |
spelling | pubmed-68614262019-11-27 Synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in Arabidopsis seedlings Oh, Keimei Hoshi, Tomoki J Pestic Sci Original Article Twenty-seven analogues of pyrazole derivatives were synthesized and subjected to structure–activity relationship studies on inducing the triple response in Arabidopsis seedlings. We found that 3,4-Dichloro-N-methyl-N-[(1-allyl-3,5-dimethyl-1H-pyrazol-4-yl)methyl]benzenesulfonamide (C26) exhibits potent activity on inducing the triple response in Arabidopsis seedlings. C26 (10 µM) induced an exaggerated apical hook in Arabidopsis seedlings. The curvature of the hook of the Arabidopsis seedlings was found to be 300±23 degrees, while ethephon (10 µM), a prodrug of ethylene, and a non-chemically treated control were found to be 128±19 and 58±16 degrees, respectively. C26 also exhibited potent activity on reducing stem elongation. The hypocotyl length of Arabidopsis seedlings treated with C26 (10 µM) was found to be 0.25±0.02 cm, while those of ethephon-treated (10 µM) and treated controls were found to be 0.69±0.06 and 1.15±0.01 cm, respectively. C26 displayed potency inhibiting the root growth of Arabidopsis seedlings similar to that of ethephon. Pesticide Science Society of Japan 2019-11-20 /pmc/articles/PMC6861426/ /pubmed/31777442 http://dx.doi.org/10.1584/jpestics.D19-037 Text en © 2019 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 | Original Article Oh, Keimei Hoshi, Tomoki Synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in Arabidopsis seedlings |
title | Synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in Arabidopsis seedlings |
title_full | Synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in Arabidopsis seedlings |
title_fullStr | Synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in Arabidopsis seedlings |
title_full_unstemmed | Synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in Arabidopsis seedlings |
title_short | Synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in Arabidopsis seedlings |
title_sort | synthesis and structure-activity relationships of new pyrazole derivatives that induce triple response in arabidopsis seedlings |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6861426/ https://www.ncbi.nlm.nih.gov/pubmed/31777442 http://dx.doi.org/10.1584/jpestics.D19-037 |
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