Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer
It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (1), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been...
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| Veröffentlicht in: | Journal of chemical ecology 2003-10, Vol.29 (10), p.2189-2199 |
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| creator | James, D.G Petroski, R.J Cosse, A.A Zilkowski, B.W Bartelt, R.J |
| description | It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (1), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a commercial red currant field in Washington State showed that synthetic racemic 1 is attractive to male J. integer under natural conditions. A clear dose-response was evident, with greatest numbers of girdlers caught in sticky traps baited with 10 mg of the pheromone (in rubber septa) and least in traps baited with 1 mg or less. During May 2002, 10, 5, 3, and 1 mg baited traps caught means of 41.4, 26.6, 6.7, and 2.7 males/trap/visit (3-5 day intervals), respectively, with a maximum of 229 males caught in a single trap baited with 5 mg. A new synthetic method for racemic 1 is presented. The absolute configuration of natural 1 from the male sawflies was determined to be (R). The potential for using the sex pheromone of J. integer to improve management of this currant and gooseberry pest is discussed. |
| doi_str_mv | 10.1023/A:1026210111334 |
| format | Article |
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These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a commercial red currant field in Washington State showed that synthetic racemic 1 is attractive to male J. integer under natural conditions. A clear dose-response was evident, with greatest numbers of girdlers caught in sticky traps baited with 10 mg of the pheromone (in rubber septa) and least in traps baited with 1 mg or less. During May 2002, 10, 5, 3, and 1 mg baited traps caught means of 41.4, 26.6, 6.7, and 2.7 males/trap/visit (3-5 day intervals), respectively, with a maximum of 229 males caught in a single trap baited with 5 mg. A new synthetic method for racemic 1 is presented. The absolute configuration of natural 1 from the male sawflies was determined to be (R). The potential for using the sex pheromone of J. integer to improve management of this currant and gooseberry pest is discussed.</description><identifier>ISSN: 0098-0331</identifier><identifier>EISSN: 1573-1561</identifier><identifier>DOI: 10.1023/A:1026210111334</identifier><identifier>PMID: 14682505</identifier><identifier>CODEN: JCECD8</identifier><language>eng</language><publisher>New York, NY: Springer</publisher><subject>9-Octadecen-4-olide ; Animal and plant ecology ; Animal, plant and microbial ecology ; Animals ; Autoecology ; Biological and medical sciences ; Cephidae ; chemical composition ; Dose-Response Relationship, Drug ; enantiomers ; Female ; field experimentation ; Field study ; Field tests ; Fundamental and applied biological sciences. Psychology ; General aspects ; Hymenoptera - chemistry ; Insect Control ; insect pests ; insect traps ; Insects ; Janus integer ; Male ; Males ; Movement ; Pheromones ; sawflies ; Sex Attractants - chemical synthesis ; Sex Attractants - chemistry ; Sex Attractants - pharmacology ; sex pheromones ; stereoisomers</subject><ispartof>Journal of chemical ecology, 2003-10, Vol.29 (10), p.2189-2199</ispartof><rights>2004 INIST-CNRS</rights><rights>Plenum Publishing Corporation 2003</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c365t-2d48f000e4f2a77f971a4ce5fbf5abcbdc40e4fbcc63f903d5b6d90cd812decd3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15291264$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14682505$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>James, D.G</creatorcontrib><creatorcontrib>Petroski, R.J</creatorcontrib><creatorcontrib>Cosse, A.A</creatorcontrib><creatorcontrib>Zilkowski, B.W</creatorcontrib><creatorcontrib>Bartelt, R.J</creatorcontrib><title>Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer</title><title>Journal of chemical ecology</title><addtitle>J Chem Ecol</addtitle><description>It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (1), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a commercial red currant field in Washington State showed that synthetic racemic 1 is attractive to male J. integer under natural conditions. A clear dose-response was evident, with greatest numbers of girdlers caught in sticky traps baited with 10 mg of the pheromone (in rubber septa) and least in traps baited with 1 mg or less. During May 2002, 10, 5, 3, and 1 mg baited traps caught means of 41.4, 26.6, 6.7, and 2.7 males/trap/visit (3-5 day intervals), respectively, with a maximum of 229 males caught in a single trap baited with 5 mg. A new synthetic method for racemic 1 is presented. The absolute configuration of natural 1 from the male sawflies was determined to be (R). The potential for using the sex pheromone of J. integer to improve management of this currant and gooseberry pest is discussed.</description><subject>9-Octadecen-4-olide</subject><subject>Animal and plant ecology</subject><subject>Animal, plant and microbial ecology</subject><subject>Animals</subject><subject>Autoecology</subject><subject>Biological and medical sciences</subject><subject>Cephidae</subject><subject>chemical composition</subject><subject>Dose-Response Relationship, Drug</subject><subject>enantiomers</subject><subject>Female</subject><subject>field experimentation</subject><subject>Field study</subject><subject>Field tests</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>Hymenoptera - chemistry</subject><subject>Insect Control</subject><subject>insect pests</subject><subject>insect traps</subject><subject>Insects</subject><subject>Janus integer</subject><subject>Male</subject><subject>Males</subject><subject>Movement</subject><subject>Pheromones</subject><subject>sawflies</subject><subject>Sex Attractants - chemical synthesis</subject><subject>Sex Attractants - chemistry</subject><subject>Sex Attractants - pharmacology</subject><subject>sex pheromones</subject><subject>stereoisomers</subject><issn>0098-0331</issn><issn>1573-1561</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNqF0UtPGzEUBWCrKoJAu-4OLKR2lSm-vvY82FHUAlWkLijrkcePxGgewZ5B5N_jKEGV2HR1JZ9P1vUxIV-AfQfG8eLqMo2cAwMARPGBzEAWmIHM4SOZMVaVGUOEI3Ic4yNjyZbykByByEsumZwR9cMPSo_-2Y-bOY2bflzZ6OOcqt5QvfJBtSmhg6MpoNG-0PXKhqEbers91FMIqh9pHG1Hlz6Y1oY5_a36KVLfj3Zpwydy4FQb7ef9PCEPv37-vb7NFn9u7q6vFpnGXI4ZN6J0aUMrHFdF4aoClNBWusZJ1ejGaLHNGq1zdBVDI5vcVEybErix2uAJ-ba7dx2Gp8nGse581LZtVW-HKdYFiIILyP8LoeIcC9zC83fwcZhCnx5RF4ipfsarhE73aGo6a-p18J0Km_qt4gS-7oGKWrUu9aV9_Ockr4DnIrmznXNqqNUyJPNwzxlg-kVMuyO-AtZblEU</recordid><startdate>20031001</startdate><enddate>20031001</enddate><creator>James, D.G</creator><creator>Petroski, R.J</creator><creator>Cosse, A.A</creator><creator>Zilkowski, B.W</creator><creator>Bartelt, R.J</creator><general>Springer</general><general>Springer Nature B.V</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>3V.</scope><scope>7QG</scope><scope>7QR</scope><scope>7SN</scope><scope>7SS</scope><scope>7U7</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PCBAR</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>20031001</creationdate><title>Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer</title><author>James, D.G ; Petroski, R.J ; Cosse, A.A ; Zilkowski, B.W ; Bartelt, R.J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c365t-2d48f000e4f2a77f971a4ce5fbf5abcbdc40e4fbcc63f903d5b6d90cd812decd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>9-Octadecen-4-olide</topic><topic>Animal and plant ecology</topic><topic>Animal, plant and microbial ecology</topic><topic>Animals</topic><topic>Autoecology</topic><topic>Biological and medical sciences</topic><topic>Cephidae</topic><topic>chemical composition</topic><topic>Dose-Response Relationship, Drug</topic><topic>enantiomers</topic><topic>Female</topic><topic>field experimentation</topic><topic>Field study</topic><topic>Field tests</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Hymenoptera - chemistry</topic><topic>Insect Control</topic><topic>insect pests</topic><topic>insect traps</topic><topic>Insects</topic><topic>Janus integer</topic><topic>Male</topic><topic>Males</topic><topic>Movement</topic><topic>Pheromones</topic><topic>sawflies</topic><topic>Sex Attractants - chemical synthesis</topic><topic>Sex Attractants - chemistry</topic><topic>Sex Attractants - pharmacology</topic><topic>sex pheromones</topic><topic>stereoisomers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>James, D.G</creatorcontrib><creatorcontrib>Petroski, R.J</creatorcontrib><creatorcontrib>Cosse, A.A</creatorcontrib><creatorcontrib>Zilkowski, B.W</creatorcontrib><creatorcontrib>Bartelt, R.J</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>ProQuest Central (Corporate)</collection><collection>Animal Behavior Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Toxicology Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of chemical ecology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>James, D.G</au><au>Petroski, R.J</au><au>Cosse, A.A</au><au>Zilkowski, B.W</au><au>Bartelt, R.J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer</atitle><jtitle>Journal of chemical ecology</jtitle><addtitle>J Chem Ecol</addtitle><date>2003-10-01</date><risdate>2003</risdate><volume>29</volume><issue>10</issue><spage>2189</spage><epage>2199</epage><pages>2189-2199</pages><issn>0098-0331</issn><eissn>1573-1561</eissn><coden>JCECD8</coden><abstract>It was previously reported that females of the currant stem girdler, Janus integer Norton (Hymenoptera: Cephidae), produce a compound, (Z)-9-octadecen-4-olide (1), that is sensitively detected by the antennae of males only. These characteristics suggested a pheromonal function, and this has now been confirmed with behavioral tests. Field tests conducted during two seasons in a commercial red currant field in Washington State showed that synthetic racemic 1 is attractive to male J. integer under natural conditions. A clear dose-response was evident, with greatest numbers of girdlers caught in sticky traps baited with 10 mg of the pheromone (in rubber septa) and least in traps baited with 1 mg or less. During May 2002, 10, 5, 3, and 1 mg baited traps caught means of 41.4, 26.6, 6.7, and 2.7 males/trap/visit (3-5 day intervals), respectively, with a maximum of 229 males caught in a single trap baited with 5 mg. A new synthetic method for racemic 1 is presented. The absolute configuration of natural 1 from the male sawflies was determined to be (R). The potential for using the sex pheromone of J. integer to improve management of this currant and gooseberry pest is discussed.</abstract><cop>New York, NY</cop><pub>Springer</pub><pmid>14682505</pmid><doi>10.1023/A:1026210111334</doi><tpages>11</tpages></addata></record> |
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| subjects | 9-Octadecen-4-olide Animal and plant ecology Animal, plant and microbial ecology Animals Autoecology Biological and medical sciences Cephidae chemical composition Dose-Response Relationship, Drug enantiomers Female field experimentation Field study Field tests Fundamental and applied biological sciences. Psychology General aspects Hymenoptera - chemistry Insect Control insect pests insect traps Insects Janus integer Male Males Movement Pheromones sawflies Sex Attractants - chemical synthesis Sex Attractants - chemistry Sex Attractants - pharmacology sex pheromones stereoisomers |
| title | Bioactivity, synthesis, and chirality of the sex pheromone of currant stem girdler, Janus integer |
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