Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups
Substituted phenylhydrazone moieties and two carbonate groups were merged in one molecule scaffold to obtain 48 novel compounds. 1H and 13C NMR, MS, elemental analysis, and X-ray single-crystal diffraction were used to confirm their structures. Bioassay results revealed that some of the compounds ha...
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ftpubmed:oai:pubmedcentral.nih.gov:6183331 2023-05-15T15:52:38+02:00 Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups Wang, Jun-Jun Si, Wei-Jie Chen, Min Lu, Ai-Min Zhang, Wei-Hua Yang, Chun-Long 2017-08-20 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6183331/ https://doi.org/10.1584/jpestics.D16-105 en eng Pesticide Science Society of Japan http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6183331/ http://dx.doi.org/10.1584/jpestics.D16-105 © 2017 Pesticide Science Society of Japan Original Article Text 2017 ftpubmed https://doi.org/10.1584/jpestics.D16-105 2018-10-28T00:14:35Z Substituted phenylhydrazone moieties and two carbonate groups were merged in one molecule scaffold to obtain 48 novel compounds. 1H and 13C NMR, MS, elemental analysis, and X-ray single-crystal diffraction were used to confirm their structures. Bioassay results revealed that some of the compounds have strong antifungal activities against Botrytis cinerea, Rhizoctonia solani, and Colletotrichum capsici (especially Rhizoctonia solani). Compound 5H1 is the most promising of the tested compounds against R. solani with an EC50 value of 1.91 mg/L, which is comparable with the positive control fungicide drazoxolon (1.94 mg/L). The structure–activity relationships against R. solani formed three rules: 1) small carbonate groups may improve the antifungal activity of the title compounds; 2) electron-withdrawing groups at the phenyl ring of phenylhydrazone are preferable to their non-substituted counterparts; and 3) halogen at the para position is more beneficial than at the ortho or meta position. Text Carbonic acid PubMed Central (PMC) Journal of Pesticide Science 42 3 84 92 |
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Original Article Wang, Jun-Jun Si, Wei-Jie Chen, Min Lu, Ai-Min Zhang, Wei-Hua Yang, Chun-Long Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups |
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Original Article |
description |
Substituted phenylhydrazone moieties and two carbonate groups were merged in one molecule scaffold to obtain 48 novel compounds. 1H and 13C NMR, MS, elemental analysis, and X-ray single-crystal diffraction were used to confirm their structures. Bioassay results revealed that some of the compounds have strong antifungal activities against Botrytis cinerea, Rhizoctonia solani, and Colletotrichum capsici (especially Rhizoctonia solani). Compound 5H1 is the most promising of the tested compounds against R. solani with an EC50 value of 1.91 mg/L, which is comparable with the positive control fungicide drazoxolon (1.94 mg/L). The structure–activity relationships against R. solani formed three rules: 1) small carbonate groups may improve the antifungal activity of the title compounds; 2) electron-withdrawing groups at the phenyl ring of phenylhydrazone are preferable to their non-substituted counterparts; and 3) halogen at the para position is more beneficial than at the ortho or meta position. |
format |
Text |
author |
Wang, Jun-Jun Si, Wei-Jie Chen, Min Lu, Ai-Min Zhang, Wei-Hua Yang, Chun-Long |
author_facet |
Wang, Jun-Jun Si, Wei-Jie Chen, Min Lu, Ai-Min Zhang, Wei-Hua Yang, Chun-Long |
author_sort |
Wang, Jun-Jun |
title |
Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups |
title_short |
Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups |
title_full |
Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups |
title_fullStr |
Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups |
title_full_unstemmed |
Synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups |
title_sort |
synthesis and fungicidal activity of phenylhydrazone derivatives containing two carbonic acid ester groups |
publisher |
Pesticide Science Society of Japan |
publishDate |
2017 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6183331/ https://doi.org/10.1584/jpestics.D16-105 |
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Carbonic acid |
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Carbonic acid |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6183331/ http://dx.doi.org/10.1584/jpestics.D16-105 |
op_rights |
© 2017 Pesticide Science Society of Japan |
op_doi |
https://doi.org/10.1584/jpestics.D16-105 |
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Journal of Pesticide Science |
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42 |
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3 |
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84 |
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92 |
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1766387759810871296 |