Identification, synthesis and activity of sex pheromone
gland components of the autumn gum moth (Lepidoptera:
Geometridae), a defoliator of Eucalyptus |
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Authors: | Martin J Steinbauer Fredrik Östrand Tom E Bellas Anna Nilson Fredrik Andersson Erik Hedenström Michael J Lacey P Florian Schiestl |
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Institution: | (1) Co-operative Research Centre (CRC) for Sustainable Production Forestry and CSIRO Entomology, 1700, ACT, 2601 Canberra, Australia;(2) Chemical Ecology and Ecotoxicology, Department of Ecology , Lund University, 223 62 Lund, Sweden;(3) CSIRO Entomology, 1700, ACT, 2601 Canberra, Australia;(4) Department of Natural and Environmental Sciences, Mid Sweden University, 851 70 Sundsvall, Sweden;(5) Department of Evolutionary Biology, University of Vienna and School of Botany and Zoology, Australian National University, ACT, 0200 Canberra, Australia;(6) Geobotanical Institute, ETH, Zollikerstrasse 107, 8008 Zürich, Switzerland |
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Abstract: | Summary. The autumn gum moth, Mnesampela privata
(Guenée) (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,6
Z,9
Z)-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. |
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Keywords: | (3Z 6Z 9Z)-3 6 9-nonadecatriene gas chromatography mass spectrometry GC– EAD EAG synthesis |
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