3Z, 13Z-octadecadienyl acetate: sex pheromone of the apple clearwing moth in British Columbia

2011 ◽  
Vol 143 (3) ◽  
pp. 236-244 ◽  
Author(s):  
Gary J.R. Judd ◽  
Regine Gries ◽  
V. Marius Aurelian ◽  
Gerhard Gries
Keyword(s):  
British Columbia ◽  
Sex Pheromone ◽  
Detection Threshold ◽  
Field Trapping ◽  
Structural Assignment ◽  
Pheromone Components ◽  
Introduced Pest ◽  
Electroantennographic Detection ◽  
Clearwing Moth ◽  
Three Components

AbstractThe apple clearwing moth, Synanthedon myopaeformis (Borkhausen) (Lepidoptera: Sesiidae), is a European species discovered in Cawston, British Columbia, Canada, in 2005. Using coupled gas chromatographic – electroantennographic detection analyses we identified candidate sex pheromone components in pheromone gland extracts and effluvia from calling females. Analysis of gland extracts using four gas-chromatography (GC) columns (DB-5, DB-17, DB-23, and DB-210) showed three components (A, B, and C) that consistently elicited strong responses from male antennae. Based on previous work, the most antennally stimulatory component, B, was hypothesized to be (3Z,13Z)-octadecadienyl acetate ((3Z,13Z)-18:OAc). Its retention time on the four GC columns and its mass spectrum in a concentrated extract matched those of an authentic standard, thus confirming structural assignment. Components A and C were below the detection threshold of the mass spectrometer, but their retention times on the four GC columns matched those of authentic standards of (3Z,13Z)-octadecadienol ((3Z,13Z)-18:OH) and (2E,13Z)-octadecadienyl acetate ((2E,13Z)-18:OAc), respectively. Synthetic (3Z,13Z)-18:OAc, (3Z,13Z)-18:OH, and (2E,13Z)-18:OAc all elicited strong responses from male antennae, further supporting structural assignments of these three components. Of these antennally active compounds, only (3Z,13Z)-18:OAc and (3Z,13Z)-18:OH were detected in effluvia from calling female moths. In field trapping tests in Cawston, (3Z,13Z)-18:OAc alone was as attractive as, or more attractive than, binary or ternary blends containing this component. (2E,13Z)-18:OAc was behaviourally inactive alone or in combination with (3Z,13Z)-18:OAc, whereas 5% (3Z,13Z)-18:OH appeared antagonistic. Our analysis confirms that (3Z,13Z)-18:OAc is the major pheromone component in S. myopaeformis, and it alone is sufficiently attractive for use in detection surveys and development of pheromone-based controls for this introduced pest in Canada.

Identification of a sex pheromone component for Pennisetia marginata (Lepidoptera: Sesiidae)

2012 ◽  
Vol 144 (6) ◽  
pp. 769-778 ◽  
Author(s):  
Gary J.R. Judd ◽  
Regine Gries ◽  
Carolyn Teasdale ◽  
Gerhard Gries
Keyword(s):  
Sex Pheromone ◽  
Field Trapping ◽  
Pheromone Component ◽  
Pheromone Gland ◽  
Active Components ◽  
Native North American ◽  
Pheromone Components ◽  
Electroantennographic Detection ◽  
Component C ◽  
Antennal Responses

AbstractRaspberry crown borer, Pennisetia marginata (Harris) (Lepidoptera: Sesiidae), is a native North American species and pest of many cane fruits. Using coupled gas chromatographic–electroantennographic detection analyses (GC-EAD) we identified candidate sex pheromone components in pheromone gland extracts and effluvia from calling females. Analysis of gland extracts on a Zebron-5 column revealed four components (A, B, C, and D) that elicited strong responses from male antennae. The two most EAD-active components A and B were hypothesised to be (3E,13Z)-octadecadienal [(3E,13Z)-18:Ald] and (3E,13Z)-octadecadienol [(3E,13Z)-18:OH], respectively. Their retention times on other GC columns matched those of authentic standards, thus supporting structural assignments. Synthetic (3E,13Z)-18:Ald, and its GC rearrangement product (2E,13Z)-octadecadienal [(2E,13Z)-18:Ald; component C], also induced antennal responses in GC-EAD analyses of female effluvia. Compounds D in pheromone gland extract, and E and F in female effluvia, elicited EAD responses but could not be identified. In field trapping experiments, (3E,13Z)-18:Ald was the only component that attracted male P. marginata when tested alone. Attractiveness of (3E,13Z)-18:Ald was reduced when combined in binary or ternary blends with any of the other identified components, suggesting one or all may act as pheromone antagonists. In Aldergrove, British Columbia, Canada, peak diel attraction of male P. marginata to (3E,13Z)-18:Ald occurred between 16:00 and 18:00 hours Pacific Daylight Time, at temperatures of 21–23°C, on 30 August 2010, 3 September 2010, and 13 September 2010. We conclude that (3E,13Z)-18:Ald is the major pheromone component of P. marginata.

Cameraria gaultheriella and C. lobatiella attracted in Canada to (E,Z)-8,10-tetradecadienal, the sex pheromone of the European C. ohridella

2006 ◽  
Vol 138 (2) ◽  
pp. 263-268 ◽  
Author(s):  
Gábor Szöcs ◽  
Imre S. Otvos ◽  
Andrea J. Schiller ◽  
Jan Bergmann ◽  
Wittko Francke
Keyword(s):  
British Columbia ◽  
Sex Pheromone ◽  
Field Trapping ◽  
Horse Chestnut ◽  
Pheromone Traps ◽  
Quercus Garryana ◽  
Gaultheria Shallon ◽  
Sticky Traps ◽  
Oak Trees ◽  
Trapping Trials

AbstractField trapping trials showed that Cameraria gaultheriella Walsingham and C. lobatiella Opler and Davis (Lepidoptera: Gracillariidae) were attracted in significant numbers in British Columbia, Canada, to sticky traps baited with 10 µg of (E,Z)-8,10-tetradecadienal (E8Z10-14Ald), the sex pheromone of the European horse chestnut leafminer, C. ohridella Deschka and Dimic. There was perfect specificity in captures at habitats located only about 8 km apart from each other: C. gaultheriella was captured exclusively at a humid habitat covered by the shrub salal, Gaultheria shallon Pursh (Ericaceae), whereas C. lobatiella was trapped at an arid location with Garry oak trees, Quercus garryana Dougl. (Fagaceae). Seasonal flight patterns of these two Canadian Cameraria species, as monitored by pheromone traps, indicated differences in their respective flight periods. The possibility of additional cryptic components in the respective pheromones of these three Cameraria species attracted to E8Z10-14Ald is discussed.

Attraction of male Mayetiola thujae (Diptera: Cecidomyiidae) to the sex-pheromone blend of (2S,12S)-, (2S,13S)-, and (2S,14S)-diacetoxyheptadecane is reduced in the presence of the SR- or RR-stereoisomers

2007 ◽  
Vol 139 (5) ◽  
pp. 685-689
Author(s):  
Regine Gries ◽  
Robb G. Bennett ◽  
Grigori Khaskin ◽  
Gerhard Gries
Keyword(s):  
British Columbia ◽  
Sex Pheromone ◽  
Seed Orchard ◽  
Field Trapping ◽  
Thuja Plicata ◽  
Red Cedar ◽  
Synthetic Pheromone ◽  
Western Red Cedar ◽  
Sex Pheromone Blend ◽  
Pheromone Blend

AbstractIn a field trapping experiment in an abandoned seed orchard of western red-cedar, Thuja plicata Donn × D. Don, in British Columbia, we show that attraction of male red-cedar cone midges, Mayetiola thujae (Hedlin), to the pheromone blend (2S,12S)-, (2S,13S)-, and (2S,14S)-diacetoxyheptadecane is reduced in the presence of a blend of all other stereoisomers, or of the three SR- or RR-stereoisomers. The three RS-stereoisomers, in contrast, had no significant effect. Thus, synthetic pheromone for monitoring M. thujae populations must not contain the SR- or RR-stereoisomers of 2,12-, 2,13-, and 2,14-diacetoxyheptadecane. This result will allow development of a less expensive design for synthesizing the pheromone.

SEX PHEROMONE COMPONENTS OF THE EYESPOTTED BUD MOTH, SPILONOTA OCELLANA (DENIS AND SCHIFFERMÜLLER) (LEPIDOPTERA: OLETHREUTIDAE)

1991 ◽  
Vol 123 (6) ◽  
pp. 1391-1394 ◽  
Author(s):  
H. McBrien ◽  
G. Gries ◽  
R. Gries ◽  
J.H. Borden ◽  
G.J.R. Judd ◽  
...  
Keyword(s):  
British Columbia ◽  
Sex Pheromone ◽  
Virgin Female ◽  
Field Tests ◽  
Monitoring And Control ◽  
Spectroscopic Analyses ◽  
Sex Pheromone Components ◽  
Pheromone Components ◽  
Tetradecenyl Acetate ◽  
And Control

AbstractZ8-tetradecenyl acetate (Z8-14OAc andZ8-tetradecenyl alcohol (Z8-14OH) were identified as sex pheromone components of the eyespotted bud moth, Spilonota ocellana (Denis and Schiffermüller) (Lepidoptera: Olethreutidae). Compounds were identified by gas chrornatographic-eleclroantennographic (GC-EAD) and GC-mass spectroscopic analyses and field tested in apple orchards in the Okanagan Valley, B.C. Although Z8-14OAc alone was attractive to male S. ocellana, the addition of 1–5% Z8-14OH strongly synergized its attraction. Field tests comparing the attractiveness of virgin female S. ocellana with various doses of a 99:1 blend of Z8-14OAc and Z8-14OH indicated the natural sex pheromone has only two significant components. A 99:1 blend of Z8-14OAC and Z8-14OH is suggested for monitoring and control of S. ocellana populations in British Columbia.

Identification of Minor Sex Pheromone Components of the Poplar Clearwing Moth Paranthrene tabaniformis (Lepidoptera, Sesiidae)

2007 ◽  
Vol 62 (1-2) ◽  
pp. 138-142 ◽  
Author(s):  
Raimondas Mozūraitis ◽  
Vidmantas Karalius
Keyword(s):  
Sex Pheromone ◽  
Synergistic Effects ◽  
Field Tests ◽  
European Part ◽  
Sex Pheromone Components ◽  
Sex Pheromone Gland ◽  
Pheromone Components ◽  
Clearwing Moth ◽  
Paranthrene Tabaniformis

A chemical analysis of the crude sex pheromone gland extracts of virgin calling Paranthrene tabaniformis females, obtained from the European part of Kazakhstan, revealed the presence of five compounds: (3E,13Z)-octadeca-3,13-dien-1-ol (E3,Z13-18:OH), (3Z,13Z)- octadeca-3,13-dien-1-ol (Z3,Z13-18:OH), (2E,13Z)-octadeca-2,13-dien-1-ol (E2,Z13-18:OH), (13Z)-octadec-13-en-1-ol (Z13-18:OH), and octadecan-1-ol (18:OH) at the ratios 64.0 : 32.4 : 1.4 : 0.9 :1.3, which are structurally related to sex pheromone components of clearwing moths. Our previous field tests showed synergistic effects of Z3,Z13-18:OH and E2,Z13-18:OH to attract P. tabaniformis males, when these compounds were tested in binary mixtures with the known sex pheromone E3,Z13-18:OH. The three dienic alcohols should all be considered as sex pheromone components of the P. tabaniformis species, while the role of Z13-18:OH and 18:OH remained unclear.

Sex pheromone and diel periodicity of Cydia strobilella (Lepidoptera: Tortricidae) pheromonal communication

2002 ◽  
Vol 134 (6) ◽  
pp. 847-850 ◽  
Author(s):  
C. Bédard ◽  
R. Gries ◽  
G. Gries ◽  
R. Bennett
Keyword(s):  
British Columbia ◽  
Sex Pheromone ◽  
Field Experiments ◽  
Pheromone Component ◽  
Diel Periodicity ◽  
Pheromonal Communication ◽  
Pheromone Components

The sex pheromone of the spruce seed moth, Cydia strobilella (L.) (Lepidoptera: Tortricidae), has not yet been identified, but several chemicals were found to be attractive to males (reviewed by Grant et al. 1989). E8-Dodecenyl acetate (E8-12:OAc) at 0.3-3.0 μg doses was the only effective attractant for males in field experiments in British Columbia, Ontario, and Newfoundland (Grant et al. 1989). Our objectives were to (i) confirm that female C. strobilella produce E8-12:OAc as a pheromone component, (ii) determine whether females produce additional pheromone components, and (iii) investigate the die1 periodicity of pheromonal communication.

Field Trapping of Chrysopa cognata (Neuroptera: Chrysopidae) with Aphid Sex Pheromone Components in Korea

2003 ◽  
Vol 6 (1) ◽  
pp. 29-36 ◽  
Author(s):  
Kyung Saeng Boo ◽  
S.S. Kang ◽  
J.H. Park ◽  
J.A. Pickett ◽  
L.J. Wadhams
Keyword(s):  
Sex Pheromone ◽  
Field Trapping ◽  
Sex Pheromone Components ◽  
Pheromone Components ◽  
Aphid Sex Pheromone

Sex pheromone components of the fruit-tree leaf roller,Archips argyrospilus (Walker) (Lepidoptera: Tortricidae), in British Columbia

1993 ◽  
Vol 19 (12) ◽  
pp. 2855-2864 ◽  
Author(s):  
J. -P. Deland ◽  
R. Gries ◽  
G. Gries ◽  
G. J. R. Judd ◽  
B. D. Roitberg
Keyword(s):  
British Columbia ◽  
Sex Pheromone ◽  
Fruit Tree ◽  
Leaf Roller ◽  
Sex Pheromone Components ◽  
Pheromone Components ◽  
Tree Leaf ◽  
Archips Argyrospilus

Synthesis and Field Tests of Sex Pheromone Components of the Leafroller Argyrotaenia sphaleropa

2004 ◽  
Vol 59 (9-10) ◽  
pp. 708-712 ◽  
Author(s):  
Sacha Legrand ◽  
Marco Botton ◽  
Peter Witzgall ◽  
Rikard Unelius
Keyword(s):  
Sex Pheromone ◽  
Wittig Reaction ◽  
Field Tests ◽  
Field Trapping ◽  
Female Pheromone ◽  
Sex Pheromone Components ◽  
Pheromone Components ◽  
Trap Catches ◽  
Pheromone Glands

Abstract Female pheromone glands of the leafroller Argyrotaenia sphaleropa were analyzed. Two acetates were identified as (11Z,13)-tetradecadien-1-yl acetate and (11Z)-tetradecen-1-yl acetate by comparison with synthesized references. The (11Z,13)-tetradecadien-1-yl acetate and the aldehyde (11Z,13)-tetradecadienal were synthesized via a Wittig reaction. A field-trapping test showed that a lure consisting of a mixture of (11Z,13)-tetradecadienal and (11Z,13)- tetradecadien-1-yl acetate in a 10:1-ratio produced the highest trap catches.

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