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- Wassgren, A.-B., et al.
(författare)
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Sex Pheromone of the Pine Sawfly Macrodiprion nemoralis (Hymenoptera : Diprionidae) : Identification of (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecanol as the Precursor for the Active Pheromone Acetate
- 2000
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Ingår i: Die Naturwissenschaften. - : Springer Science and Business Media LLC. - 0028-1042 .- 1432-1904. ; 87:1, s. 24-29
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Tidskriftsartikel (refereegranskat)abstract
- The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7,9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography-mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic threo peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field, confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate.
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- Anderbrant, O., et al.
(författare)
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Electrophysiological and morphological characteristics of pheromone receptors in male pine sawflies, Diprion pini (Hymenoptera : Diprionidae), and behavioural response to some compounds
- 1995
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Ingår i: Journal of Insect Physiology. - : Elsevier BV. - 0022-1910. ; 41:5, s. 395-401
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Tidskriftsartikel (refereegranskat)abstract
- The morphology and physiology of pheromone receptors on the antennae of male pine sawflies, Diprion pini L., were investigated. Using scanning electron microscopy, five sensillar types were recognized. The type shown to be pheromone sensitive has a long (50-70 μm) cuticular hair, is single-walled, and is innervated by 8 or 9 sensory cells as revealed by transmission electron microscopy. Electroantennography (EAG) showed similar activity of the acetate and propionate of (2S,3R,7R)-3,7-dimethyl-2-tridecanol, precursor of the main constituent of the female-produced sex pheromone. No other isomer induced any significant response. Single-sensillum recordings confirmed the results of the EAG, and also showed that several neurons were excited by the active compound. EAG recordings and combined gas chromatographic-electroantennographic detection indicated that esters of three 3,7-dimethyl-2-pentadecanol (diprionol) isomers were active, but field tests could not demonstrate any behavioural effect. Diprionol esters are used as sex pheromones by all other pine sawflies investigated so far, and D. pini is thus the first diprionid species shown to use a different sex pheromone.
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- Anderbrant, Olle, et al.
(författare)
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Field response of the pine sawfly Neodiprion sertifer to the pheromone (2S, 3S, 7S)‐diprionyl acetate and its stereoisomers
- 1992
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Ingår i: Entomologia Experimentalis et Applicata. - : Wiley. - 0013-8703. ; 62:2, s. 169-181
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Tidskriftsartikel (refereegranskat)abstract
- All eight optical isomers of 3,7‐dimethyl‐2‐pentadecanyl acetate (diprionyl acetate), of high optical purity (>97.4%), were tested for a behavioural activity on male pine sawflies, Neodiprion sertifer (Geoffr.) (Hymenoptera: Diprionidae), in northern Europe. Males were strongly attracted to (2S, 3S, 7S)‐diprionyl acetate. Addition of more than 0.1% of the (2S, 3R, 7R)‐isomer reduced the catch and above 2% the attraction was completely inhibited. Contrary to what has been reported for North American and Japanese populations, so significant synergistic effect of small amounts of the (2S, 3R, 7R)‐isomer could be demonstrated. The effects of addition of the other six optical isomers alone or in combinations, were also studied, but none was found to be a synergist. The (2S, 3R, 7S)‐isomer had a weak inhibitory effect, and completely inhibited the attraction to the (2S, 3S, 7S)‐isomer when applied in about equal amounts as the attractant. In some cases a reduction in catch was noted when other isomers were tested, but this could be attributed to the very small amounts of the inhibitory (2S, 3R, 7R)‐isomer present in these isomers. 1992 The Netherlands Entomological Society
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