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Identification and Syntheses of Semiochemicals Affecting Mnesampela privata and Trioza apicalis
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics. (Organisk kemi, Erik Hedenström)
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 [en]
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: urn:nbn:se:miun:diva-10596ISBN: 978-91-86073-61-9 (print)OAI: oai:DiVA.org:miun-10596DiVA, id: diva2:280212
Presentation
2009-12-18, O111, Holmgatan 10, Sundsvall, 13:00 (Swedish)
Opponent
Supervisors
Available from: 2009-12-09 Created: 2009-12-08 Last updated: 2009-12-11Bibliographically approved
List of papers
1. Identification, synthesis and activity of sex pheromone gland components of the autumn gum moth (Lepidoptera: Geometridae), a defoliator of Eucalyptus
Open this publication in new window or tab >>Identification, synthesis and activity of sex pheromone gland components of the autumn gum moth (Lepidoptera: Geometridae), a defoliator of Eucalyptus
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2004 (English)In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 14, no 3-4, p. 217-223Article in journal (Refereed) Published
Abstract [en]

The autumn gum moth, Mnesampela privata (Guenee) (Lepidoptera: Geometridae), is native to Australia and can be a pest of plantation eucalypts. Field-collected and laboratory-reared female autumn gum moths were dissected to remove glands likely to contain components of the sex pheromone. Using gas chromatography (GC) and combined gas chromatography-mass spectrometry (GC-MS), three compounds were identified from female extracts, namely (3Z,6Z,9Z)-3,6,9-nonadecatriene, 1-hexadecanol and 1-octadecanol (confirmed by comparison with synthetic samples). Nonadecatriene elicited an antennal response in male autumn gum moth during gas chromatographic analyses combined with electroantennographic detection (GC-EAD). In electroantennogram (EAG) recording male M. privata antennae responded to the nonadecatriene. Nonadecatriene was synthesised via Kolbe electrolysis, starting with (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid (linolenic acid) and propanoic acid or via an alternative four-step method also starting from linolenic acid. In field trials (3Z,6Z,9Z)-3,6,9-nonadecatriene proved attractive to male moths. Thus, we conclude that (3Z,6Z,9Z)-3,6,9-nonadecatriene is a sex pheromone component of autumn gum moth. This component has been identified in extracts from other geometrids in the same subfamily, Ennominae. However, to our knowledge this is the first example where (3Z,6Z,9Z)-3,6,9-nonadecatriene has been found in females and also proved attractive to male moths when presented on its own. Our results are discussed in relation to other geometrid pheromones.

National Category
Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-2414 (URN)10.1007/s00049-004-0281-5 (DOI)000224526000011 ()2-s2.0-6344241062 (Scopus ID)2393 (Local ID)2393 (Archive number)2393 (OAI)
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2017-12-12Bibliographically approved
2. 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
Open this publication in new window or tab >>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.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:miun:diva-10200 (URN)10.1007/s10886-009-9717-2 (DOI)000274206600002 ()2-s2.0-76349084938 (Scopus ID)
Available from: 2009-10-29 Created: 2009-10-27 Last updated: 2017-12-12Bibliographically approved

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