Synthesis and bioactivity of (13Z,15E)-octadecadienal: A sex pheromone component from Micromelalopha siversi Staudinger (Lepidoptera: Notodontidae).
Identifieur interne : 000095 ( Main/Exploration ); précédent : 000094; suivant : 000096Synthesis and bioactivity of (13Z,15E)-octadecadienal: A sex pheromone component from Micromelalopha siversi Staudinger (Lepidoptera: Notodontidae).
Auteurs : Fu Liu [République populaire de Chine] ; Li Guo [République populaire de Chine] ; Sufang Zhang [République populaire de Chine] ; Xiangbo Kong [République populaire de Chine] ; Zhen Zhang [République populaire de Chine]Source :
- Pest management science [ 1526-4998 ] ; 2020.
Abstract
BACKGROUND
Micromelalopha siversi (Staudinger) (Lepidoptera: Notodontidae) is a defoliator of poplar trees, Populus spp. (Salicaceae). In our previous study, 13,15-octadecadienal has been conformed as a female-produced candidate sex pheromone component of M. siversi, but the Z/E stereochemistry of the 1,3-diene system has not been identified so far.
RESULTS
Four unsaturated aliphatic aldehydes, Z13,E15-18:Ald, Z13,Z15-18:Ald, E13,E15-18:Ald, and E13,Z15-18:Ald, were synthesized from the commercially available 12-bromo-1-decanol mainly by alkylation of lithium alkyne, normal Wittig or Wittig-Schlosser olefination, and hydroboration-protonolysis. According to gas chromatography (GC) analysis of pheromone gland extracts, Z13,E15-18:Ald was the main component, and a small amount of Z13,Z15-18:Ald was also detected, with a ratio of approximately 7:3. However, the results of GC-electroantennographic detection (GC-EAD) showed that Z13,E15-18:Ald was the only compound with electrophysiological activity, whereas Z13,Z15-18:Ald elicited no activity. In the field, traps baited with only Z13,E15-18:Ald resulted in much superior results to those with Z13,Z15-18:Ald as well as the Z13,E15-18:Ald and Z13,Z15-18:Ald binary mixture.
CONCLUSIONS
Based on geometrically selective synthesis and bioactivity tests, the active sex pheromone component of M. siversi has been identified as Z13,E15-18:Ald, the pheromone component that has not been identified in Lepidoptera before. The synthetic component was attractive to male moths in preliminary field traps, which provides novel technologies to monitor and control this pest.
DOI: 10.1002/ps.6015
PubMed: 32696568
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Li" uniqKey="Guo L" first="Li" last="Guo">Li Guo</name><affiliation wicri:level="1"><nlm:affiliation>School of Biological Science and Engineering, Xingtai University, Xingtai, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Biological Science and Engineering, Xingtai University, Xingtai</wicri:regionArea><wicri:noRegion>Xingtai</wicri:noRegion></affiliation></author><author><name sortKey="Zhang, Sufang" sort="Zhang, Sufang" uniqKey="Zhang S" first="Sufang" last="Zhang">Sufang Zhang</name><affiliation wicri:level="3"><nlm:affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key 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sort="Zhang, Zhen" uniqKey="Zhang Z" first="Zhen" last="Zhang">Zhen Zhang</name><affiliation wicri:level="3"><nlm:affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing</wicri:regionArea><placeName><settlement type="city">Pékin</settlement></placeName></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2020">2020</date><idno type="RBID">pubmed:32696568</idno><idno type="pmid">32696568</idno><idno type="doi">10.1002/ps.6015</idno><idno type="wicri:Area/Main/Corpus">000180</idno><idno 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Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing</wicri:regionArea><placeName><settlement type="city">Pékin</settlement></placeName></affiliation></author><author><name sortKey="Guo, Li" sort="Guo, Li" uniqKey="Guo L" first="Li" last="Guo">Li Guo</name><affiliation wicri:level="1"><nlm:affiliation>School of Biological Science and Engineering, Xingtai University, Xingtai, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Biological Science and Engineering, Xingtai University, Xingtai</wicri:regionArea><wicri:noRegion>Xingtai</wicri:noRegion></affiliation></author><author><name sortKey="Zhang, Sufang" sort="Zhang, Sufang" uniqKey="Zhang S" first="Sufang" last="Zhang">Sufang Zhang</name><affiliation wicri:level="3"><nlm:affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing</wicri:regionArea><placeName><settlement type="city">Pékin</settlement></placeName></affiliation></author><author><name sortKey="Kong, Xiangbo" sort="Kong, Xiangbo" uniqKey="Kong X" first="Xiangbo" last="Kong">Xiangbo Kong</name><affiliation wicri:level="3"><nlm:affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing</wicri:regionArea><placeName><settlement type="city">Pékin</settlement></placeName></affiliation></author><author><name sortKey="Zhang, Zhen" sort="Zhang, Zhen" uniqKey="Zhang Z" first="Zhen" last="Zhang">Zhen Zhang</name><affiliation wicri:level="3"><nlm:affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing</wicri:regionArea><placeName><settlement type="city">Pékin</settlement></placeName></affiliation></author></analytic><series><title level="j">Pest management science</title><idno type="eISSN">1526-4998</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p><b>BACKGROUND</b></p><p>Micromelalopha siversi (Staudinger) (Lepidoptera: Notodontidae) is a defoliator of poplar trees, Populus spp. (Salicaceae). In our previous study, 13,15-octadecadienal has been conformed as a female-produced candidate sex pheromone component of M. siversi, but the Z/E stereochemistry of the 1,3-diene system has not been identified so far.</p></div><div type="abstract" xml:lang="en"><p><b>RESULTS</b></p><p>Four unsaturated aliphatic aldehydes, Z13,E15-18:Ald, Z13,Z15-18:Ald, E13,E15-18:Ald, and E13,Z15-18:Ald, were synthesized from the commercially available 12-bromo-1-decanol mainly by alkylation of lithium alkyne, normal Wittig or Wittig-Schlosser olefination, and hydroboration-protonolysis. According to gas chromatography (GC) analysis of pheromone gland extracts, Z13,E15-18:Ald was the main component, and a small amount of Z13,Z15-18:Ald was also detected, with a ratio of approximately 7:3. However, the results of GC-electroantennographic detection (GC-EAD) showed that Z13,E15-18:Ald was the only compound with electrophysiological activity, whereas Z13,Z15-18:Ald elicited no activity. In the field, traps baited with only Z13,E15-18:Ald resulted in much superior results to those with Z13,Z15-18:Ald as well as the Z13,E15-18:Ald and Z13,Z15-18:Ald binary mixture.</p></div><div type="abstract" xml:lang="en"><p><b>CONCLUSIONS</b></p><p>Based on geometrically selective synthesis and bioactivity tests, the active sex pheromone component of M. siversi has been identified as Z13,E15-18:Ald, the pheromone component that has not been identified in Lepidoptera before. The synthetic component was attractive to male moths in preliminary field traps, which provides novel technologies to monitor and control this pest.</p></div></front></TEI><pubmed><MedlineCitation Status="Publisher" Owner="NLM"><PMID Version="1">32696568</PMID><DateRevised><Year>2020</Year><Month>08</Month><Day>31</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1526-4998</ISSN><JournalIssue CitedMedium="Internet"><PubDate><Year>2020</Year><Month>Jul</Month><Day>21</Day></PubDate></JournalIssue><Title>Pest management science</Title><ISOAbbreviation>Pest Manag Sci</ISOAbbreviation></Journal><ArticleTitle>Synthesis and bioactivity of (13Z,15E)-octadecadienal: A sex pheromone component from Micromelalopha siversi Staudinger (Lepidoptera: Notodontidae).</ArticleTitle><ELocationID EIdType="doi" ValidYN="Y">10.1002/ps.6015</ELocationID><Abstract><AbstractText Label="BACKGROUND" NlmCategory="BACKGROUND">Micromelalopha siversi (Staudinger) (Lepidoptera: Notodontidae) is a defoliator of poplar trees, Populus spp. (Salicaceae). In our previous study, 13,15-octadecadienal has been conformed as a female-produced candidate sex pheromone component of M. siversi, but the Z/E stereochemistry of the 1,3-diene system has not been identified so far.</AbstractText><AbstractText Label="RESULTS" NlmCategory="RESULTS">Four unsaturated aliphatic aldehydes, Z13,E15-18:Ald, Z13,Z15-18:Ald, E13,E15-18:Ald, and E13,Z15-18:Ald, were synthesized from the commercially available 12-bromo-1-decanol mainly by alkylation of lithium alkyne, normal Wittig or Wittig-Schlosser olefination, and hydroboration-protonolysis. According to gas chromatography (GC) analysis of pheromone gland extracts, Z13,E15-18:Ald was the main component, and a small amount of Z13,Z15-18:Ald was also detected, with a ratio of approximately 7:3. However, the results of GC-electroantennographic detection (GC-EAD) showed that Z13,E15-18:Ald was the only compound with electrophysiological activity, whereas Z13,Z15-18:Ald elicited no activity. In the field, traps baited with only Z13,E15-18:Ald resulted in much superior results to those with Z13,Z15-18:Ald as well as the Z13,E15-18:Ald and Z13,Z15-18:Ald binary mixture.</AbstractText><AbstractText Label="CONCLUSIONS" NlmCategory="CONCLUSIONS">Based on geometrically selective synthesis and bioactivity tests, the active sex pheromone component of M. siversi has been identified as Z13,E15-18:Ald, the pheromone component that has not been identified in Lepidoptera before. The synthetic component was attractive to male moths in preliminary field traps, which provides novel technologies to monitor and control this pest.</AbstractText><CopyrightInformation>© 2020 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Fu</ForeName><Initials>F</Initials><Identifier Source="ORCID">https://orcid.org/0000-0001-9955-959X</Identifier><AffiliationInfo><Affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Guo</LastName><ForeName>Li</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>School of Biological Science and Engineering, Xingtai University, Xingtai, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhang</LastName><ForeName>Sufang</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kong</LastName><ForeName>Xiangbo</ForeName><Initials>X</Initials><AffiliationInfo><Affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhang</LastName><ForeName>Zhen</ForeName><Initials>Z</Initials><AffiliationInfo><Affiliation>Research Institute of Forest Ecology, Environment and Protection, Chinese Academy of Forestry, Key Laboratory of Forest Protection of National Forestry and Grassland Administration, Beijing, China.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>6194044</GrantID><Agency>Beijing Natural Science Foundation</Agency><Country></Country></Grant><Grant><GrantID>CAFYBB2016QA008</GrantID><Agency>Institute Special Fund for Basic Research, Institute of Forest Ecology, Environment, and Protection, Chinese Academy of Forestry</Agency><Country></Country></Grant><Grant><GrantID>31901320</GrantID><Agency>National Natural Science Foundation of China</Agency><Country></Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>07</Month><Day>21</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Pest Manag Sci</MedlineTA><NlmUniqueID>100898744</NlmUniqueID><ISSNLinking>1526-498X</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Micromelalopha siversi</Keyword><Keyword MajorTopicYN="N">Z13,E15-18:Ald</Keyword><Keyword MajorTopicYN="N">chemical synthesis</Keyword><Keyword MajorTopicYN="N">sex pheromone</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2020</Year><Month>04</Month><Day>01</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>07</Month><Day>16</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>07</Month><Day>21</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>7</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>7</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>7</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>aheadofprint</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32696568</ArticleId><ArticleId IdType="doi">10.1002/ps.6015</ArticleId></ArticleIdList><ReferenceList><Title>REFERENCES</Title><Reference><Citation>Heilman PE, Planted Forests: Poplars, in New Forest, Springer Netherlands, NETHERLANDS. 17:89-93 (1999). https://doi.org/10.1023/A:1006515204167</Citation></Reference><Reference><Citation>André AD, Wrege PH, Sydenstricker KV and Cerretani J, Clone preference by nesting birds in short-rotation coppice plantations in central and western New York. Biomass Bioenergy 27:429-435 (2004).</Citation></Reference><Reference><Citation>Berlizov AN, Blum OB, Filby RH, Maliyuk IA and Tryshyn VV, Testing applicability of black poplar (Populus nigra L.) bark to heavy metal air pollution monitoring in urban and industrial regions. Sci Total Environ 372:693-706 (2007).</Citation></Reference><Reference><Citation>Robinson BH, Green SR, Chancerel B, Mills TM and Clothier BE, Poplar for the phytomanagement of boron contaminated sites. Environ Pollut 150:225-233 (2007).</Citation></Reference><Reference><Citation>Dickmann DI, Silviculture and biology of short-rotation woody crops in temperate regions: then and now. Biomass Bioenergy 30:696-705 (2006).</Citation></Reference><Reference><Citation>Aylott MJ, Casella E, Tubby I, Street NR, Smith P and Taylor G, Yield and spatial supply of bioenergy poplar and willow short-rotation coppice in the UK. New Phytol 178:358-370 (2008).</Citation></Reference><Reference><Citation>Horemans JA, Arriga N and Ceulemans R, Greenhouse gas budget of a poplar bioenergy plantation in Belgium: CO2 uptake outweighs CH4 and N2O emissions. GCB Bioenergy 11:1435-1443 (2019).</Citation></Reference><Reference><Citation>Ventura M, Panzacchi P, Muzzi E, Magnani F and Tonon G, Carbon balance and soil carbon input in a poplar short rotation coppice plantation as affected by nitrogen and wood ash application. New For 50:969-990 (2019).</Citation></Reference><Reference><Citation>Guo TB, Ji BZ, Zhu GQ and Huang MR, Effect of transgenic poplars on the activities of detoxification enzymes in Micromelalopha troglodyta larvae. Sci Silva Sin 43:59-63 (2007).</Citation></Reference><Reference><Citation>Fan LP, Zhang Z, Liu YX, Yu ZJ, Kong XB, Wang HB, et al., Factors impacting the emergence rhythm and rate of Micromelalopha sieversi (Lepidoptera: Notodontidae), Forest Res 27:53-58 (2014).</Citation></Reference><Reference><Citation>Guo L, Liu F, Zhang SF, Kong XB and Zhang Z, Egg deposition of Micromelalopha sieversi (Staudinger) on clones of Populus from section Aigeiros induces resistance in neighboring plants. Forests 10:110 (2019).</Citation></Reference><Reference><Citation>Fan LP, Huang FQ, Wang HB, Kong XB, Zhang SF and Zhang Z, Reproductive behavior of Micromelalopha sieversi (Lepidoptera: Notodontidae). Sci Silva Sin 51:60-66 (2015).</Citation></Reference><Reference><Citation>Chen L, Wang GL and Wei HY, Circadian rhythm of emergence and reproduction of Micromelalopha troglodyta (Lepidoptera: Notodontidae). Chin J Appl Ecol 25:2425-2430 (2014).</Citation></Reference><Reference><Citation>Tang F, Zhang XB, Liu YS and Gao XW, In vitro inhibition of glutathione S-transferases by several insecticides and allelochemicals in two moth species. Int J Pest Manage 60:33-38 (2014).</Citation></Reference><Reference><Citation>Cheng H, Tang F, Li W and Xu M, Tannic acid induction of a glutathione S-transferase in Micromelalopha siversi (Lepidoptera: Notodontidae) larvae. J Entomol Sci 50:350-362 (2016).</Citation></Reference><Reference><Citation>Baker TC, Zhu JJ and Millar JG, Delivering on the promise of pheromones. J Chem Ecol 42:553-556 (2016).</Citation></Reference><Reference><Citation>Larsson MC, Pheromones and other semiochemicals for monitoring rare and endangered species. J Chem Ecol 42:853-868 (2016).</Citation></Reference><Reference><Citation>Liu F, Guo L, Li QC, Zhang SF, Kong XB, Zhang Z, et al., Identification of the active components of sex pheromone of female moths of Micromelalopha sieversi (Lepidoptera: Notodontidae), Acta Entom Sin 62:814-822 (2019).</Citation></Reference><Reference><Citation>Ando T, Inomata S and Yamamoto M, Lepidopteran sex pheromones. Top Curr Chem 239:51-96 (2004).</Citation></Reference><Reference><Citation>Jurenka R, Insect pheromone biosynthesis. Top Curr Chem. 239: 97-132 (2004).</Citation></Reference><Reference><Citation>Frérot B, Malosse C, Milat ML, Demolin G, Martin JC, Khemici M, et al., Chemical analysis of the sex pheromone glands of Thaumetopoea bonjeani (Powell) (Lepidoptera., Thaumetopoeidae), J Appl Entomol 109:210-212 (1990).</Citation></Reference><Reference><Citation>Guerrero A, Camps F, Coll J, Riba M, Einhorn J, Descoins Ch, et al., Identification of a potential sex pheromone of the processionary moth Thaumetopoea pityocampa (Lepitoptera, Notodontidae), Tetrahedron Lett 22:2013-2016 (1981).</Citation></Reference><Reference><Citation>Halperin J, Mating disruption of the pine processionary caterpillar by pityolure. Phytoparasitica 13:221-224 (1985).</Citation></Reference><Reference><Citation>Breuer M, Kontzog HG and Loof AD, The sex attractant pheromone of the oak processionary, Thaumetopoea processionea a field evaluation. Commun Agric Appl Biol Sci 68:203-208 (2003).</Citation></Reference><Reference><Citation>Silk P, Lonergan G, Allen D and Spear-O'mara J, Potential sex pheromone components of the saddled prominent (Lepidoptera: Notodontidae). Can Entomol 132:681-684 (2000).</Citation></Reference><Reference><Citation>Bestmann HJ, Kern F, Schaefer D and Vostrowsky O, (11Z,13Z)-11,13-Hexadecadienal, the sex pheromone of females of Notodonta dromedaries. Naturwissenschaften 24:271-273 (1993).</Citation></Reference><Reference><Citation>Bestmann HJ, Kern F and Schäfer D, Vostrowsky O, and Hasenfuss I, (11Z,13Z)-11,13-Hexadecadienyl acetate, the sex pheromone of females of Notodonta torva. Naturwissenschaften 78:465-467 (1991).</Citation></Reference><Reference><Citation>Frérot B and Demolin G, Sex pheromone of the processionary moths and biosystematic considerations within the genus Thaumetopoea (Thaumetopoeidae Thaumetopoeinae). Boll Zool Agrar Bachic Ser II 25:33-40 (1993).</Citation></Reference><Reference><Citation>Furber M, Taylor RJ and Burford SC, Z,Z-dienes via acetylene carbocupration: synthesis of navel orangeworm pheromone. Tetrahedron Lett 26:3285-3288 (1985).</Citation></Reference><Reference><Citation>Zhao CH, Adlof RO and Löfstedt C, Sex pheromone biosynthesis in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera: Lasiocampidae): pathways leading to Z5-monoene and 5,7-conjugated diene components. Insect Biochem Mol 34:261-271 (2004).</Citation></Reference><Reference><Citation>Kong XB, Zhao CH and Wang R, Sex pheromone of the larch caterpillar moth, Dendrolimus superans, from northeastern China. Entomol Exp Appl 124:37-44 (2007).</Citation></Reference><Reference><Citation>Kong XB, Sun XL, Wang HB, Zhang Z, Zhao CH and Booij KCJH, Identification of components of the female sex pheromone of the simao pine caterpillar moth, dendrolimus kikuchii matsumura. J Chem Ecol 37:412-419 (2011).</Citation></Reference><Reference><Citation>Kong XB, Liu KW, Wang HB, Zhang SF and Zhang Z, Identification and behavioral evaluation of sex pheromone components of the Chinese pine caterpillar moth, dendrolimus tabulaeformis. PLoS One 7:e33381 (2012).</Citation></Reference><Reference><Citation>Liu F, Kong XB, Zhang SF and Zhang Z, Facile and efficient syntheses of (11Z,13Z)-hexadecadienal and its derivatives: key sex pheromone and attractant components of Notodontidae. Molecules 24:1781 (2019).</Citation></Reference><Reference><Citation>Witzgall P, Bengtsson M, Rauscher S, Liblikas I, Bäckman A-C, Coracini M, et al., Identification of further sex pheromone synergists in the codling moth, cydia pomonella, Entomol Exp Appl 101:131-141 (2001).</Citation></Reference><Reference><Citation>Katovich SA, Swedenborg PD, Giblin M and Underhill EW, Evidence for (E,Z)-8,10-dodecadienyl acetate as the major component of the sex pheromone of the eastern pine seedworm, cydia toreuta (lepidoptera: tortricidae). J Chem Ecol 15:581-590 (1989).</Citation></Reference><Reference><Citation>Davis HG, Mcdonough LM, Jr BA and Bierl-Leonhardt BA, Filbertworm sex pheromone: identification and field tests of (E,E)- and (E,Z)-8,10-dodecadien-1-ol acetates. J Chem Ecol 10:53-61 (1984).</Citation></Reference><Reference><Citation>Wang Z, Lu XY, Lei AW and Zhang ZG, Efficient preparation of functionalized (E,Z) dienes using acetylene as the building block. J Org Chem 63:3806-3807 (1998).</Citation></Reference><Reference><Citation>Juri JC, Fielder S and Vigneswaran M, Synthesis of 6Z,8E-heneicosadien-11-one, a sex pheromone of the painted apple moth, Teia anartoides. Tetrahedron Lett 44:27-28 (2003).</Citation></Reference><Reference><Citation>Mori K, New synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm. Biosci Biotechnol Biochem 73:2727-2730 (2009).</Citation></Reference><Reference><Citation>Tao YH, Yang XM, Jin Y and Wang QZ, Facile synthesis of (Z,E)-9,11-hexadecadienal, the major sex pheromone component of the sugarcane borer diatraea saccharalis: an efficient strategy for synthesis of (Z,E)-dienic pheromones. Synth Commun 43:415-424 (2013).</Citation></Reference><Reference><Citation>Santangelo EM, Coracini M, Witzgall P, Arlene G and Unelius RC, Identification, syntheses, and characterization of the geometric isomers of 9,11-hexadecadienal from female pheromone glands of the sugar cane borer, Diatraea saccharalis. J Nat Prod 65:909-915 (2002).</Citation></Reference><Reference><Citation>Ragoussis V, Perdikaris S, Karamolegkos A and Magkiosi K, Improved synthesis of (3E,7Z)-3,7-Tetradecadienyl acetate, the major sex pheromone constituent of the potato pest Symmetrischema tangolias (Gyen). J Agric Food Chem 56:11929-11932 (2008).</Citation></Reference><Reference><Citation>Khrimian A, Klun JA, Hijji Y, Baranchikov YN, Pet'ko VM, Mastro V et al., Syntheses of (Z,E)-5,7-dodecadienol and (E,Z)-10,12-hexadecadienol, Lepidoptera pheromone components, via zinc reduction of enyne precursors. Test of pheromone efficacy against the Siberian moth. J Agric Food Chem 50:6366-6370 (2002).</Citation></Reference><Reference><Citation>Hedin P, Davis FM, Dickens JC, Burks ML, Bird TG and Knutson AE, Identification of the sex attractant pheromone of the southwestern corn borer Diatraea grandiosella Dyar. J Chem Ecol 12:2051-2063 (1986).</Citation></Reference><Reference><Citation>Hodgson DM and Arif T, Convergent and stereoselective synthesis of trisubstituted E-alkenyl bromides and iodides via β-oxido phosphonium ylides. J Am Chem Soc 130:16500-16501 (2008).</Citation></Reference><Reference><Citation>Hodgson DM and Arif T, Convergent synthesis of trisubstituted Z-allylic esters by Wittig-schlosser reaction. Org Lett 12:4204-4207 (2010).</Citation></Reference><Reference><Citation>Schlosser M and Christmann KF, Trans-selective olefin syntheses. Angew Chem Int Ed 5:126 (1966).</Citation></Reference><Reference><Citation>Schlosser M, Huynh BT and Schaub B, The betaine-ylide route to trans-alkenols. Tetrahedron Lett 26:311-314 (1985).</Citation></Reference></ReferenceList></PubmedData></pubmed><affiliations><list><country><li>République populaire de Chine</li></country><settlement><li>Pékin</li></settlement></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Liu, Fu" sort="Liu, Fu" uniqKey="Liu F" first="Fu" last="Liu">Fu Liu</name></noRegion><name sortKey="Guo, Li" sort="Guo, Li" uniqKey="Guo L" first="Li" last="Guo">Li Guo</name><name sortKey="Kong, Xiangbo" sort="Kong, Xiangbo" uniqKey="Kong X" first="Xiangbo" last="Kong">Xiangbo Kong</name><name sortKey="Zhang, Sufang" sort="Zhang, Sufang" uniqKey="Zhang S" first="Sufang" last="Zhang">Sufang Zhang</name><name sortKey="Zhang, Zhen" sort="Zhang, Zhen" uniqKey="Zhang Z" first="Zhen" last="Zhang">Zhen Zhang</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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