Unusual pheromone chemistry in the navel orangeworm: novel sex attractants and a behavioral antagonist

Using molecular- and sensory physiology-based approaches, three novel natural products, a simple ester, and a behavioral antagonist have been identified from the pheromone gland of the navel orangeworm, Amyelois transitella Walker (Lepidoptera: Pyralidae). In addition to the previously identified (Z...

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Bibliographic Details
Published in:Die Naturwissenschaften 2005-03, Vol.92 (3), p.139-146
Main Authors: Leal, W.S, Parra-Pedrazzoli, A.L, Kaissling, K.E, Morgan, T.I, Zalom, F.G, Pesak, D.J, Dundulis, E.A, Burks, C.S, Higbee, B.S
Format: Article
Language:English
Subjects:
11,13-hexadecadien-1-yl acetate
Amyelois transitella
Animals
antagonists
antennae
Behavior, Animal
chemical composition
Chromatography, Gas
cross-species attraction
electroantennography
electrophysiology
ethyl palmitate
ethyl-(Z,Z)-11,13-hexadecadienoate
Larva
Lepidoptera
Lepidoptera - growth & development
Lepidoptera - physiology
mating behavior
pentacosapentaene
pheromone antagonists
pheromone blends
pheromone glands
pheromone traps
Pupa
Pyralidae
Pyralis farinalis
sex attractants
Sex Attractants - chemistry
Sex Attractants - physiology
sex pheromones
Sexual Behavior, Animal
trapping
tricosapentaene
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Summary:Using molecular- and sensory physiology-based approaches, three novel natural products, a simple ester, and a behavioral antagonist have been identified from the pheromone gland of the navel orangeworm, Amyelois transitella Walker (Lepidoptera: Pyralidae). In addition to the previously identified (Z,Z)-11,13-hexadecadienal, the pheromone blend is composed of (Z,Z,Z,Z,Z)-3,6,9,12,15-tricosapentaene, (Z,Z,Z,Z,Z)-3,6,9,12,15-pentacosapentaene, ethyl palmitate, ethyl-(Z,Z)-11,13-hexadecadienoate, and (Z,Z)-11,13-hexadecadien-1-yl acetate. The C23 and C25 pentaenes are not only novel sex pheromones, but also new natural products. In field tests, catches of A. transitella males in traps baited with the full mixture of pheromones were as high as those in traps with virgin females, whereas control and traps baited only with the previously known constituent did not capture any moths at all. The navel orangeworm sex pheromone is also an attractant for the meal moth, Pyralis farinalis L. (Pyralidae), but (Z,Z)-11,13-hexadecadien-1-yl acetate is a behavioral antagonist. The new pheromone blend may be highly effective in mating disruption and monitoring programs.
ISSN:1432-1904
0028-1042
1432-1904
DOI:10.1007/s00114-004-0598-5