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...
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| Veröffentlicht in: | Journal of Pesticide Science 2021/05/20, Vol.46(2), pp.189-197 |
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| creator | Suzuki, Jun Ootaka, Akihito Onoue, Shinji Onoue, Miwa |
| 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. |
| doi_str_mv | 10.1584/jpestics.D21-007 |
| format | Article |
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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.</description><identifier>ISSN: 1348-589X</identifier><identifier>EISSN: 1349-0923</identifier><identifier>DOI: 10.1584/jpestics.D21-007</identifier><identifier>PMID: 34135680</identifier><language>eng</language><publisher>Tokyo: Pesticide Science Society of Japan</publisher><subject>acaricidal activity ; Alkylation ; Chemical synthesis ; Iodine ; phenylpiperazine ; Phosphorus ; Piperazine ; Reagents ; Regular ; Substitution reactions ; Tetranychus kanzawai and Panonychus citri ; Tetranychus urticae</subject><ispartof>Journal of Pesticide Science, 2021/05/20, Vol.46(2), pp.189-197</ispartof><rights>Pesticide Science Society of Japan 2021. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) License (https://creativecommons.org/licenses/by-nc-nd/4.0/)</rights><rights>2021. This work is published under https://creativecommons.org/licenses/by-nc-nd/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2021 Pesticide Science Society of Japan 2021 Pesticide Science Society of Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c722t-51be411f42c8fd6de5c949c673de613617879b4df8b42442d61327594b482efd3</citedby><cites>FETCH-LOGICAL-c722t-51be411f42c8fd6de5c949c673de613617879b4df8b42442d61327594b482efd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8175216/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8175216/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,1877,27901,27902,53766,53768</link.rule.ids></links><search><creatorcontrib>Suzuki, Jun</creatorcontrib><creatorcontrib>Ootaka, Akihito</creatorcontrib><creatorcontrib>Onoue, Shinji</creatorcontrib><creatorcontrib>Onoue, Miwa</creatorcontrib><creatorcontrib>Hokko Chemical Industry Co</creatorcontrib><creatorcontrib>Ltd</creatorcontrib><title>Synthesis and acaricidal activity of phenylpiperazine derivatives</title><title>Journal of Pesticide Science</title><addtitle>J. Pestic. Sci.</addtitle><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.</description><subject>acaricidal activity</subject><subject>Alkylation</subject><subject>Chemical synthesis</subject><subject>Iodine</subject><subject>phenylpiperazine</subject><subject>Phosphorus</subject><subject>Piperazine</subject><subject>Reagents</subject><subject>Regular</subject><subject>Substitution reactions</subject><subject>Tetranychus kanzawai and Panonychus citri</subject><subject>Tetranychus urticae</subject><issn>1348-589X</issn><issn>1349-0923</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdUU1v1DAQjRCIVqV3jpG4cEnx98cFqSptQarEAZC4WY496XrldYKdXSn8erzdZSu4zIzG770Zz2uatxhdYa7Yh_UEZQ6uXH0iuENIvmjOMWW6Q5rQl0-16rjSP8-ay1LWCCEsqdRavG7OKMOUC4XOm-tvS5pXUEJpbfKtdTYHF7yNtZzDLsxLOw7ttIK0xClMkO3vkKD1kMPOVgCUN82rwcYCl8d80fy4u_1-87l7-Hr_5eb6oXOSkLnjuAeG8cCIU4MXHrjTTDshqQeBqcBSSd0zP6ieEcaIr00iuWY9UwQGTy-ajwfdadtvwDtIc7bRTDlsbF7MaIP59yWFlXkcd0ZhyQkWVeD9USCPv7b1dmYTioMYbYJxWwzhjFBRT8Mq9N1_0PW4zal-r6Io10hqRCoKHVAuj6VkGE7LYGT2Fpm_FplqkakWVcr9gVL3DM7GMcV6zmd1t9A9xxmCnhhMoJoINwgrXYOWVGGF8V7p7qC0LrN9hNNom-vACM-jmTBkH44rnABuZbOBRP8AQR-1iA</recordid><startdate>20210520</startdate><enddate>20210520</enddate><creator>Suzuki, Jun</creator><creator>Ootaka, Akihito</creator><creator>Onoue, Shinji</creator><creator>Onoue, Miwa</creator><general>Pesticide Science Society of Japan</general><general>Japan Science and Technology Agency</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SS</scope><scope>7ST</scope><scope>7TK</scope><scope>7U7</scope><scope>C1K</scope><scope>SOI</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20210520</creationdate><title>Synthesis and acaricidal activity of phenylpiperazine derivatives</title><author>Suzuki, Jun ; Ootaka, Akihito ; Onoue, Shinji ; Onoue, Miwa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c722t-51be411f42c8fd6de5c949c673de613617879b4df8b42442d61327594b482efd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>acaricidal activity</topic><topic>Alkylation</topic><topic>Chemical synthesis</topic><topic>Iodine</topic><topic>phenylpiperazine</topic><topic>Phosphorus</topic><topic>Piperazine</topic><topic>Reagents</topic><topic>Regular</topic><topic>Substitution reactions</topic><topic>Tetranychus kanzawai and Panonychus citri</topic><topic>Tetranychus urticae</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Suzuki, Jun</creatorcontrib><creatorcontrib>Ootaka, Akihito</creatorcontrib><creatorcontrib>Onoue, Shinji</creatorcontrib><creatorcontrib>Onoue, Miwa</creatorcontrib><creatorcontrib>Hokko Chemical Industry Co</creatorcontrib><creatorcontrib>Ltd</creatorcontrib><collection>CrossRef</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Environment Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Environment Abstracts</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of Pesticide Science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Suzuki, Jun</au><au>Ootaka, Akihito</au><au>Onoue, Shinji</au><au>Onoue, Miwa</au><aucorp>Hokko Chemical Industry Co</aucorp><aucorp>Ltd</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and acaricidal activity of phenylpiperazine derivatives</atitle><jtitle>Journal of Pesticide Science</jtitle><addtitle>J. Pestic. Sci.</addtitle><date>2021-05-20</date><risdate>2021</risdate><volume>46</volume><issue>2</issue><spage>189</spage><epage>197</epage><pages>189-197</pages><issn>1348-589X</issn><eissn>1349-0923</eissn><abstract>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.</abstract><cop>Tokyo</cop><pub>Pesticide Science Society of Japan</pub><pmid>34135680</pmid><doi>10.1584/jpestics.D21-007</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | acaricidal activity Alkylation Chemical synthesis Iodine phenylpiperazine Phosphorus Piperazine Reagents Regular Substitution reactions Tetranychus kanzawai and Panonychus citri Tetranychus urticae |
| title | Synthesis and acaricidal activity of phenylpiperazine derivatives |
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