Triunsaturated hydrocarbons, sex pheromone components ofCaenurgina erechtea

Underhill, E. W.; Palaniswamy, P.; Abrams, Suzanne R.; Bailey, B. K.; Steck, Warren; Chisholm, M. D.

doi:10.1007/bf00990747

Cited by 40 publications

(12 citation statements)

References 20 publications

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“…The positions of the four double bonds in the alcohol portion of the major compound were identified by the m/z 108 ion in its mass spectrum and by ozonolysis. The m/z 108 ion (58%) has been shown to be characteristic of [CH3CH 2 (CH=CH)3H] § produced by a 3,6,9-triene, counting from the methyl end of the chain (Connor et al, 1980;Underhill et al, 1983). In a docosatetraene isobutyrate, this corresponds to double bonds in the 13,16,19-positions.…”

Section: Resultsmentioning

confidence: 99%

Identification of sex pheromone of browntail moth,Euproctis chrysorrhoea (L.) (Lepidoptera: Lymantriidae)

Schwarz

et al. 1991

J Chem Ecol

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A unique sex attractant pheromone was isolated and identified from extracts of ovipositor tips from the female browntail moth (Lepidoptera: Lymantriidae). The pheromone compound, (Z,Z,Z,Z)-7,13,16,19-docosatetraen-1-ol isobutyrate, CH3CH2CH=CHCH2CH=CHCH2CH= CH(CH2)4CH=CH(CH2)6O2CCH(CH3)2, was identified by a combination of gas chromatography, mass spectrometry, and microreactions and was confirmed by synthesis. Traps baited with 5-50 μg of the synthetic pheromone, dispensed from rubber septa treated with an antioxidant and a UV stabilizer, gave male moth captures that were comparable to traps baited with three virgin females. Higher (250 μg) and lower (0.04-2.5 μg quantities of the synthetic pheromone on septa captured somewhat fewer males. Captures were the same for similar quantities of the natural and synthetic pheromone. Minor, inactive components in the tip extract were identified as a mixture of 7- and 8-pentacosanone.

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Section: Resultsmentioning

confidence: 99%

Identification of sex pheromone of browntail moth,Euproctis chrysorrhoea (L.) (Lepidoptera: Lymantriidae)

Schwarz

et al. 1991

J Chem Ecol

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“…The polyenic hydrocarbons (3 Z ,6 Z ,9 Z )‐3,6,9‐nona‐decatriene (3 Z ,6 Z ,9 Z ‐19:H) and (3 Z ,6 Z ,9 Z )‐3,6,9‐heneicosatriene (3Z, 6Z ,9 Z ‐21:H) were prepared from linolenic acid according to Underhill et al. (). A second batch of 3 Z ,6 Z ,9 Z ‐19:H used in field trials was synthesized as described by Wang and Zhang ().…”

Section: Methodsmentioning

confidence: 99%

Sex pheromone of the cloaked pug moth, Eupithecia abietaria (Lepidoptera: Geometridae), a pest of spruce cones

Wang

Svensson

Jakobsson

et al. 2014

J Applied Entomology

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The sex pheromone of the cloaked pug moth, Eupithecia abietaria G€ otze, an important cone-feeding pest in spruce seed orchards in Europe, was investigated. Chemical and electrophysiological analyses of pheromone gland extracts of female moths and analogous analyses of synthetic hydrocarbons and epoxides of chain length C 19 and C 21 revealed (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) and 3Z,6Z-cis-9,10-epoxynonadecadiene (3Z,6Z-cis-9,10-epoxy-19:H) as candidate pheromone components, which were found in a gland extract in a ratio of 95 : 5. In field trapping experiments, conspecific males were only attracted to a combination of 3Z,6Z,9Z-19:H and the (9S,10R)-enantiomer of 3Z,6Z-cis-9,10-epoxy-19:H. The (9R,10S)-enantiomer was not attractive, which is in agreement with studies on other Eupithecia species, for which males have only been attracted by the (9S,10R)-enantiomer of epoxides. Subsequent experiments showed that E. abietaria males were attracted to a wide range of ratios of the two active compounds and that trap catches increased with increasing dose of the binary blend. A twocomponent bait containing 300 lg 3Z,6Z,9Z-19:H and 33 lg of the (9S,10R)-enantiomer of 3Z,6Z-cis-9,10-epoxy-19:H was efficient for monitoring E. abietaria in spruce seed orchards in southern Sweden, where this species has probably been overlooked as an important pest in the past. With sex pheromones recently identified for two other moths that are major pests on spruce cones, the spruce seed moth, Cydia strobilella L., and the spruce coneworm, Dioryctria abietella Denis & Schifferm€ uller, pheromone-based monitoring can now be achieved for the whole guild of conefeeding moths in European spruce seed orchards.

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“…A hexane solution of the pheromone blend of T. mynesalis was prepared at 1 mg/ml of 3Z,9Z-6S,7R-epoxy-heneicosadiene (3Z,9Z-6S,7R-epoxy-21:H; 94.15% enantiomeric purity, or 88.3% enantiomeric excess; synthesized as described by Millar & Underhill 1986) and 1 mg/ml of 3Z,6Z,9Z-heneicosatriene (3Z,6Z,9Z-21:H; 96.4% pure; synthesized as described by Underhill et al 1983). Fifty ml of one of these solutions was applied to the inside well of the large diameter end of an 11mm rubber septum (A. H. Thomas, Swedesboro, New Jersey, USA) that had been extracted twice in methylene chloride.…”

Section: Periodicity Of Trap Response Of Mothsmentioning

confidence: 99%

Aggressive chemical mimicry of moth pheromones by a bolas spider: how does this specialist predator attract more than one species of prey?

et al. 2002

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The bolas spider, Mastophora hutchinsoni, attracts Lacinipolia renigera and Tetanolita mynesalis males by mimicking the female moth sex pheromones. However, as the prey species use completely different pheromone blends we conducted experiments to determine how this is accomplished by the predator. The periodicity of L. renigera mate-seeking activities occurs early in the scotophase, whereas male T. mynesalis are active late at night, corresponding with periods when these moths are captured by the spider. The pheromone blend of early-flying L. renigera interferes with attraction of late-flying T. mynesalis to its pheromone in a dose-dependent manner, suggesting the spider must always produce a single sub-optimal ''compromise'' blend for both species or that it adjusts its allomonal blend to optimize capture of the respective prey species at different times during the night. We delayed (L. renigera) or advanced (T. mynesalis) the periodicity of male activity through photoperiodic manipulation and found that the bolas spider attracted both prey species outside their normal activity windows. These results support the idea that bolas spiders produce components of both species at all times rather than producing the pheromone of each prey species at different times of the night. However, using coupled gas chromatography-electroantennography, we also demonstrated that the spider decreases its emission of the L. renigera pheromone over the course of the night. This modification should reduce the behavioral antagonism of the L. renigera pheromone on T. mynesalis males and increase the predator's success of attracting T. mynesalis during this prey's normal activity window late at night.

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Triunsaturated hydrocarbons, sex pheromone components ofCaenurgina erechtea

Cited by 40 publications

References 20 publications

Identification of sex pheromone of browntail moth,Euproctis chrysorrhoea (L.) (Lepidoptera: Lymantriidae)

Identification of sex pheromone of browntail moth,Euproctis chrysorrhoea (L.) (Lepidoptera: Lymantriidae)

Sex pheromone of the cloaked pug moth, Eupithecia abietaria (Lepidoptera: Geometridae), a pest of spruce cones

Aggressive chemical mimicry of moth pheromones by a bolas spider: how does this specialist predator attract more than one species of prey?

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