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Identification, Synthesis and Field Testing of (3Z,6Z,9Z)-3,6,9-Henicosatriene, a Second Bioactive Component of the Sex Pheromone of the Autumn Gum Moth, Mnesampela privata
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2009 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 35, no 12, p. 1411-1422Article in journal (Refereed) Published
Abstract [en]

Abstract - The sex pheromone of Mnesampela privata, an endemic pest of Eucalyptus plantations in Australia, was previously identified as containing a single bioactive compound, (3Z,6Z,9Z)-3,6,9-nonadecatriene (C19 triene). Initial field testing of lures containing 1, 5 or 10 mg of C19 triene (>98% purity) caught no or very few male M. privata. (3Z,6Z,9Z)-3,6,9-Henicosatriene (C21 triene) was identified as an additional minor pheromone component in abdominal tip extracts of M. privata females from Tasmania. Levels of C19 and C21 trienes extracted from individual females varied greatly, but the ratio was relatively constant at 33:1. Electroantennograms (EAG) of synthetic C21 triene with male M. privata gave positive but consistently lower responses than elicited by the C19 triene. Field tests showed that the addition of 1-6% C21 triene to 1mg C19 triene significantly increased trap catch and the detection of M. privata in plantations. Traps baited with a 16:1 ratio caught significantly more moths than those baited with a ratio approximating that of females.

Place, publisher, year, edition, pages
2009. Vol. 35, no 12, p. 1411-1422
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-10200DOI: 10.1007/s10886-009-9717-2ISI: 000274206600002Scopus ID: 2-s2.0-76349084938OAI: oai:DiVA.org:miun-10200DiVA, id: diva2:274300
Available from: 2009-10-29 Created: 2009-10-27 Last updated: 2017-12-12Bibliographically approved
In thesis
1. Identification and Syntheses of Semiochemicals Affecting Mnesampela privata and Trioza apicalis
Open this publication in new window or tab >>Identification and Syntheses of Semiochemicals Affecting Mnesampela privata and Trioza apicalis
2009 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

The Autumn gum moth, Mnesampela privata (Lepidoptera: Geometridae) is an endemic Australian moth whose larvae feed upon species of Eucalyptus. The moths favorite host plants are E. globulus and E. nitens which are the most important species used in commercial plantations of the Australian pulpwood industry. The autumn gum moth has become one of the most significant outbreak insects of eucalyptus plantations throughout Australia. As a consequence great financial losses to the forest industry occur. Today insecticides such as pyrethroids are used for control of eucalyptus defoliators as M. privata.

The carrot psyllid, Trioza apicalis (Homoptera: Psylloidea), is one of the major pests of carrot (Daucus carota) in northern Europe. The psyllid causes curling of the carrot leafs and reduction of plant growth. Today the carrot crops are protected with the pyrethroid insecticide cypermethrin, which is toxic to aquatic organisms and is, from 2010, prohibited for use in Sweden by the Swedish Chemicals Inspectorate.

An alternative to insecticides is to protect the seedlings with semiochemicals, a chemical substance or mixture of them that carries a message. This thesis describes the identification and the syntheses of semiochemicals from the above mentioned insect species.

From analysis of abdominal tip extracts of M. privata females from Tasmania a blend of (3Z,6Z,9Z)-3,6,9-nonadecatriene and (3Z,6Z,9Z)-3,6,9-heneicosatriene was identified as the sex pheromone of this species. The identification of the C19- and C21-trienes was confirmed by synthesis.

In the analysis of carrot leaf extracts we found a compound, α-cis-bergamotene, that induces antennal response in the carrot psyllid. This is just the beginning of the studies of trying to manipulate this psyllid with semiochemicals instead of insecticides.

Place, publisher, year, edition, pages
Sundsvall: Mid Sweden University, 2009. p. 51
Series
Mid Sweden University licentiate thesis, ISSN 1652-8948 ; 43
Keywords
Mnesampela privata, semiochemicals, pheromones, kairomones, (3Z, 6Z, 9Z)-3, 6, 9-nonadecatriene, (3Z, 6Z, 9Z)-3, 6, 9-heneicosatriene, carrot psyllid, Trioza apicalis
National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-10596 (URN)978-91-86073-61-9 (ISBN)
Presentation
2009-12-18, O111, Holmgatan 10, Sundsvall, 13:00 (Swedish)
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Available from: 2009-12-09 Created: 2009-12-08 Last updated: 2009-12-11Bibliographically approved

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Nilsson, AnnaAndersson, FredrikHedenström, Erik

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