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Synthesis and acaricidal activity of phenylpiperazine derivatives
We synthesized 33 new phenylpiperazine derivatives and assessed their acaricidal activity. These derivatives were synthesized through sequential reactions consisting of the sulfonylation of 2-substituted 4-methylaniline with chlorosulfonic acid, reduction with red phosphorus and iodine, alkylation b...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Pesticide Science Society of Japan
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8175216/ https://www.ncbi.nlm.nih.gov/pubmed/34135680 http://dx.doi.org/10.1584/jpestics.D21-007 |
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author | Suzuki, Jun Ootaka, Akihito Onoue, Shinji Onoue, Miwa |
author_facet | Suzuki, Jun Ootaka, Akihito Onoue, Shinji Onoue, Miwa |
author_sort | Suzuki, Jun |
collection | PubMed |
description | We synthesized 33 new phenylpiperazine derivatives and assessed their acaricidal activity. These derivatives were synthesized through sequential reactions consisting of the sulfonylation of 2-substituted 4-methylaniline with chlorosulfonic acid, reduction with red phosphorus and iodine, alkylation by alkyl halide, cyclization with bis(2-chloroethyl)amine hydrochloride, and N-substitution reaction of phenylpiperazines with various reagents. All phenylpiperazines synthesized were evaluated for acaricidal activity and their structure–activity relationships discussed, it was found that 4-substituted 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]piperazine derivatives exhibited good acaricidal activity. Among them, 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-4-(trifluoromethylsulfonyl) piperazine showed the highest level of activity against Tetranychus urticae and provided a high level of activity against Tetranychus kanzawai and Panonychus citri. In addition, studies on the effect at various stages of T. urticae exhibited that this compound showed good activity against both adults and eggs. |
format | Online Article Text |
id | pubmed-8175216 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Pesticide Science Society of Japan |
record_format | MEDLINE/PubMed |
spelling | pubmed-81752162021-06-15 Synthesis and acaricidal activity of phenylpiperazine derivatives Suzuki, Jun Ootaka, Akihito Onoue, Shinji Onoue, Miwa J Pestic Sci Regular Article We synthesized 33 new phenylpiperazine derivatives and assessed their acaricidal activity. These derivatives were synthesized through sequential reactions consisting of the sulfonylation of 2-substituted 4-methylaniline with chlorosulfonic acid, reduction with red phosphorus and iodine, alkylation by alkyl halide, cyclization with bis(2-chloroethyl)amine hydrochloride, and N-substitution reaction of phenylpiperazines with various reagents. All phenylpiperazines synthesized were evaluated for acaricidal activity and their structure–activity relationships discussed, it was found that 4-substituted 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]piperazine derivatives exhibited good acaricidal activity. Among them, 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-4-(trifluoromethylsulfonyl) piperazine showed the highest level of activity against Tetranychus urticae and provided a high level of activity against Tetranychus kanzawai and Panonychus citri. In addition, studies on the effect at various stages of T. urticae exhibited that this compound showed good activity against both adults and eggs. Pesticide Science Society of Japan 2021-05-20 /pmc/articles/PMC8175216/ /pubmed/34135680 http://dx.doi.org/10.1584/jpestics.D21-007 Text en © 2021 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 Suzuki, Jun Ootaka, Akihito Onoue, Shinji Onoue, Miwa Synthesis and acaricidal activity of phenylpiperazine derivatives |
title | Synthesis and acaricidal activity of phenylpiperazine derivatives |
title_full | Synthesis and acaricidal activity of phenylpiperazine derivatives |
title_fullStr | Synthesis and acaricidal activity of phenylpiperazine derivatives |
title_full_unstemmed | Synthesis and acaricidal activity of phenylpiperazine derivatives |
title_short | Synthesis and acaricidal activity of phenylpiperazine derivatives |
title_sort | synthesis and acaricidal activity of phenylpiperazine derivatives |
topic | Regular Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8175216/ https://www.ncbi.nlm.nih.gov/pubmed/34135680 http://dx.doi.org/10.1584/jpestics.D21-007 |
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