G. Gries et al., (Z)6,(E)8-HENEICOSADIEN-11-ONE - SYNERGISTIC SEX-PHEROMONE COMPONENT OF DOUGLAS-FIR TUSSOCK MOTH, ORGYIA-PSEUDOTSUGATA (MCDUNNOUGH) (LEPIDOPTERA, LYMANTRIIDAE), Journal of chemical ecology, 23(1), 1997, pp. 19-34
Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and
(Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified
in pheromone gland extracts of female Douglas-fir tussock moths (DFTM)
, Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram q
uantities in extracts and structural conversion during analytical proc
edures and bioassays complicated chemical identifications. Complete id
entification required comparative analyses of stereoselectively synthe
sized and female-produced dienones by coupled gas chromatographic-elec
troantennographic detection (GC-EAD), high-performance liquid chromato
graphy (HPLC) and coupled GC-mass spectrometry (MS). Determination of
the pheromone component was contingent upon an experimental design tha
t minimized structural rearrangement of dienones before and during the
field test. In a 40-min field experiment, acetonitrile solutions of e
ach of the above dienones were carried on Dry Ice to traps and were sy
ringed onto cotton release devices below trap lids. In combination wit
h the previously known sex pheromone component of DFTM, (Z)6-heneicose
n-11-one (Z6), Z6E8 was the only synergistic dienone and the mixture w
as highly attractive. Because Z6 by itself attracts seven species of t
ussock moths (two sympatric with DFTM), a blend of Z6 and Z6E8 may imp
art specificity to DFTM pheromone communication. In commercial lures,
this binary blend may facilitate species-specific, sensitive monitorin
g and efficacious control by mating disruption of this important fores
t defoliator.