Synthesis, insecticidal activity and pyrethroidal mode of action of new tin ether derivatives
A novel range of trimethylstanniomethyl ethers of well known pyrethroid alcohols were synthesised, and their insecticidal activities and modes of action as insecticides were investigated. Among them, ethers from three types of alcohol (3‐phenoxybenzyl, 4‐fluoro‐3‐phenoxybenzyl and 6‐phenoxy‐2‐pyridy...
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| Veröffentlicht in: | Pesticide Science 1989, Vol.25 (1), p.17-23 |
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| creator | Tsushima, K Yano, T Umeda, K Matsuo, N Hirano, M Ohno, N |
| description | A novel range of trimethylstanniomethyl ethers of well known pyrethroid alcohols were synthesised, and their insecticidal activities and modes of action as insecticides were investigated. Among them, ethers from three types of alcohol (3‐phenoxybenzyl, 4‐fluoro‐3‐phenoxybenzyl and 6‐phenoxy‐2‐pyridylmethyl) showed remarkable insecticidal activities against rice stem borers, houseflies and German cockroaches.
According to electrophysiological studies on the abdominal nerve cords of German cockroaches, trimethylstanniomethyl 6‐phenoxy‐2‐pyridylmethyl ether induced a rapid decline in spontaneous firing similar to that from tetramethrin. However, insecticidal trimethyltin chloride caused an entirely different response.
These observations suggest that the present tin ether derivatives resemble pyrethroids, rather than the insecticidal tin compounds known so far. |
| doi_str_mv | 10.1002/ps.2780250104 |
| format | Article |
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According to electrophysiological studies on the abdominal nerve cords of German cockroaches, trimethylstanniomethyl 6‐phenoxy‐2‐pyridylmethyl ether induced a rapid decline in spontaneous firing similar to that from tetramethrin. However, insecticidal trimethyltin chloride caused an entirely different response.
These observations suggest that the present tin ether derivatives resemble pyrethroids, rather than the insecticidal tin compounds known so far.</description><identifier>ISSN: 0031-613X</identifier><identifier>ISSN: 1526-498X</identifier><identifier>EISSN: 1096-9063</identifier><identifier>DOI: 10.1002/ps.2780250104</identifier><identifier>CODEN: PSSCBG</identifier><language>eng</language><publisher>London: John Wiley & Sons, Ltd</publisher><subject>alcohols ; Biological and medical sciences ; Blattella germanica ; Chemical control ; Chilo suppressalis ; Control ; ethers ; Fundamental and applied biological sciences. Psychology ; insecticidal properties ; Musca domestica ; Phytopathology. Animal pests. Plant and forest protection ; Protozoa. Invertebrates ; pyrethrins ; structure-activity relationships ; synthesis ; tin</subject><ispartof>Pesticide Science, 1989, Vol.25 (1), p.17-23</ispartof><rights>Copyright © 1989 John Wiley & Sons, Ltd</rights><rights>1990 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4044-3bbecb52f1bc42b3e5318e936efdaf4c4ccb8d8dad1dc74ae1ed5c736931f413</citedby><cites>FETCH-LOGICAL-c4044-3bbecb52f1bc42b3e5318e936efdaf4c4ccb8d8dad1dc74ae1ed5c736931f413</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fps.2780250104$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fps.2780250104$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,4009,27848,27902,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6617983$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Tsushima, K</creatorcontrib><creatorcontrib>Yano, T</creatorcontrib><creatorcontrib>Umeda, K</creatorcontrib><creatorcontrib>Matsuo, N</creatorcontrib><creatorcontrib>Hirano, M</creatorcontrib><creatorcontrib>Ohno, N</creatorcontrib><title>Synthesis, insecticidal activity and pyrethroidal mode of action of new tin ether derivatives</title><title>Pesticide Science</title><addtitle>Pestic. Sci</addtitle><description>A novel range of trimethylstanniomethyl ethers of well known pyrethroid alcohols were synthesised, and their insecticidal activities and modes of action as insecticides were investigated. Among them, ethers from three types of alcohol (3‐phenoxybenzyl, 4‐fluoro‐3‐phenoxybenzyl and 6‐phenoxy‐2‐pyridylmethyl) showed remarkable insecticidal activities against rice stem borers, houseflies and German cockroaches.
According to electrophysiological studies on the abdominal nerve cords of German cockroaches, trimethylstanniomethyl 6‐phenoxy‐2‐pyridylmethyl ether induced a rapid decline in spontaneous firing similar to that from tetramethrin. However, insecticidal trimethyltin chloride caused an entirely different response.
These observations suggest that the present tin ether derivatives resemble pyrethroids, rather than the insecticidal tin compounds known so far.</description><subject>alcohols</subject><subject>Biological and medical sciences</subject><subject>Blattella germanica</subject><subject>Chemical control</subject><subject>Chilo suppressalis</subject><subject>Control</subject><subject>ethers</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>insecticidal properties</subject><subject>Musca domestica</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Protozoa. Invertebrates</subject><subject>pyrethrins</subject><subject>structure-activity relationships</subject><subject>synthesis</subject><subject>tin</subject><issn>0031-613X</issn><issn>1526-498X</issn><issn>1096-9063</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>K30</sourceid><recordid>eNp9kM1v1DAQxS1EJZaWI2ciwZG044_Y8RFVsFBVFLHl44Isxx5Tl20S7PQj_z3e7qqIC6cZaX7vzdMj5DmFQwrAjsZ8yFQLrAEK4hFZUNCy1iD5Y7IA4LSWlH9_Qp7mfAkAWmu-ID9Wcz9dYI75dRX7jG6KLnq7rmzZbuI0V7b31TgnnC7ScH-5GjxWQ7gnhn6z9XhbTbGvCoOp8pjijS1qzAdkL9h1xme7uU_O3709P35fn54tPxy_Oa2dACFq3nXouoYF2jnBOo4Npy1qLjF4G4QTznWtb7311DslLFL0jVNcak6DoHyfvNzajmn4fY15MpfDderLR0NbpSiTreaFqreUS0POCYMZU7yyaTYUzKZAM2bzt8DCv9q52uzsOiTbu5gfRFJSpduNrdpit3GN8_89zafVPw92gWKe8O5BadMvIxVXjfn2cWnEV90s28_UnBT-xZYPdjD2ZyphvqwYUA6sNMGA8T-cMZog</recordid><startdate>1989</startdate><enddate>1989</enddate><creator>Tsushima, K</creator><creator>Yano, T</creator><creator>Umeda, K</creator><creator>Matsuo, N</creator><creator>Hirano, M</creator><creator>Ohno, N</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><general>London :John Wiley & Sons Ltd</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7WH</scope><scope>K30</scope><scope>PAAUG</scope><scope>PAWHS</scope><scope>PAWZZ</scope><scope>PAXOH</scope><scope>PBHAV</scope><scope>PBQSW</scope><scope>PBYQZ</scope><scope>PCIWU</scope><scope>PCMID</scope><scope>PCZJX</scope><scope>PDGRG</scope><scope>PDWWI</scope><scope>PETMR</scope><scope>PFVGT</scope><scope>PGXDX</scope><scope>PIHIL</scope><scope>PISVA</scope><scope>PJCTQ</scope><scope>PJTMS</scope><scope>PLCHJ</scope><scope>PMHAD</scope><scope>PNQDJ</scope><scope>POUND</scope><scope>PPLAD</scope><scope>PQAPC</scope><scope>PQCAN</scope><scope>PQCMW</scope><scope>PQEME</scope><scope>PQHKH</scope><scope>PQMID</scope><scope>PQNCT</scope><scope>PQNET</scope><scope>PQSCT</scope><scope>PQSET</scope><scope>PSVJG</scope><scope>PVMQY</scope><scope>PZGFC</scope></search><sort><creationdate>1989</creationdate><title>Synthesis, insecticidal activity and pyrethroidal mode of action of new tin ether derivatives</title><author>Tsushima, K ; Yano, T ; Umeda, K ; Matsuo, N ; Hirano, M ; Ohno, N</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4044-3bbecb52f1bc42b3e5318e936efdaf4c4ccb8d8dad1dc74ae1ed5c736931f413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>alcohols</topic><topic>Biological and medical sciences</topic><topic>Blattella germanica</topic><topic>Chemical control</topic><topic>Chilo suppressalis</topic><topic>Control</topic><topic>ethers</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>insecticidal properties</topic><topic>Musca domestica</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>Protozoa. Invertebrates</topic><topic>pyrethrins</topic><topic>structure-activity relationships</topic><topic>synthesis</topic><topic>tin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tsushima, K</creatorcontrib><creatorcontrib>Yano, T</creatorcontrib><creatorcontrib>Umeda, K</creatorcontrib><creatorcontrib>Matsuo, N</creatorcontrib><creatorcontrib>Hirano, M</creatorcontrib><creatorcontrib>Ohno, N</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Periodicals Index Online Segment 50</collection><collection>Periodicals Index Online</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - West</collection><collection>Primary Sources Access (Plan D) - International</collection><collection>Primary Sources Access & Build (Plan A) - MEA</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - Midwest</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - Northeast</collection><collection>Primary Sources Access (Plan D) - Southeast</collection><collection>Primary Sources Access (Plan D) - North Central</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - Southeast</collection><collection>Primary Sources Access (Plan D) - South Central</collection><collection>Primary Sources Access & Build (Plan A) - UK / I</collection><collection>Primary Sources Access (Plan D) - Canada</collection><collection>Primary Sources Access (Plan D) - EMEALA</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - North Central</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - South Central</collection><collection>Primary Sources Access & Build (Plan A) - International</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - International</collection><collection>Primary Sources Access (Plan D) - West</collection><collection>Periodicals Index Online Segments 1-50</collection><collection>Primary Sources Access (Plan D) - APAC</collection><collection>Primary Sources Access (Plan D) - Midwest</collection><collection>Primary Sources Access (Plan D) - MEA</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - Canada</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - UK / I</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - EMEALA</collection><collection>Primary Sources Access & Build (Plan A) - APAC</collection><collection>Primary Sources Access & Build (Plan A) - Canada</collection><collection>Primary Sources Access & Build (Plan A) - West</collection><collection>Primary Sources Access & Build (Plan A) - EMEALA</collection><collection>Primary Sources Access (Plan D) - Northeast</collection><collection>Primary Sources Access & Build (Plan A) - Midwest</collection><collection>Primary Sources Access & Build (Plan A) - North Central</collection><collection>Primary Sources Access & Build (Plan A) - Northeast</collection><collection>Primary Sources Access & Build (Plan A) - South Central</collection><collection>Primary Sources Access & Build (Plan A) - Southeast</collection><collection>Primary Sources Access (Plan D) - UK / I</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - APAC</collection><collection>Primary Sources Access—Foundation Edition (Plan E) - MEA</collection><jtitle>Pesticide Science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tsushima, K</au><au>Yano, T</au><au>Umeda, K</au><au>Matsuo, N</au><au>Hirano, M</au><au>Ohno, N</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, insecticidal activity and pyrethroidal mode of action of new tin ether derivatives</atitle><jtitle>Pesticide Science</jtitle><addtitle>Pestic. Sci</addtitle><date>1989</date><risdate>1989</risdate><volume>25</volume><issue>1</issue><spage>17</spage><epage>23</epage><pages>17-23</pages><issn>0031-613X</issn><issn>1526-498X</issn><eissn>1096-9063</eissn><coden>PSSCBG</coden><abstract>A novel range of trimethylstanniomethyl ethers of well known pyrethroid alcohols were synthesised, and their insecticidal activities and modes of action as insecticides were investigated. Among them, ethers from three types of alcohol (3‐phenoxybenzyl, 4‐fluoro‐3‐phenoxybenzyl and 6‐phenoxy‐2‐pyridylmethyl) showed remarkable insecticidal activities against rice stem borers, houseflies and German cockroaches.
According to electrophysiological studies on the abdominal nerve cords of German cockroaches, trimethylstanniomethyl 6‐phenoxy‐2‐pyridylmethyl ether induced a rapid decline in spontaneous firing similar to that from tetramethrin. However, insecticidal trimethyltin chloride caused an entirely different response.
These observations suggest that the present tin ether derivatives resemble pyrethroids, rather than the insecticidal tin compounds known so far.</abstract><cop>London</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/ps.2780250104</doi><tpages>7</tpages></addata></record> |
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| ispartof | Pesticide Science, 1989, Vol.25 (1), p.17-23 |
| issn | 0031-613X 1526-498X 1096-9063 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete; Periodicals Index Online |
| subjects | alcohols Biological and medical sciences Blattella germanica Chemical control Chilo suppressalis Control ethers Fundamental and applied biological sciences. Psychology insecticidal properties Musca domestica Phytopathology. Animal pests. Plant and forest protection Protozoa. Invertebrates pyrethrins structure-activity relationships synthesis tin |
| title | Synthesis, insecticidal activity and pyrethroidal mode of action of new tin ether derivatives |
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