| 1. |
- Anderbrant, Olle, et al.
(författare)
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Field response of the pine sawfly Neodiprion sertifer to controlled release of diprionyl acetate, diprionyl propionate and trans-perillenal
- 1992
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 18:10, s. 1707-1725
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Tidskriftsartikel (refereegranskat)abstract
- Two dispenser types for pine sawfly (Hymenoptera: Diprionidae) pheromones-glass capillaries and dental cotton rolls-are described, and release rates reported. Glass capillaries of different diameters were used in field tests to determine dose-response relationships of (2 S,3 S,7 S)-3,7-dimethylpentadecan-2-yl acetate (diprionyl acetate), diprionyl propionate, and trans-perillenal on the trap catch of male Neodiprion sertifer. A linear relationship between the logarithm of the capillary cross-sectional area and the logarithm of the release rate was found. However, capillaries of the same diameter could vary in the amount released by as much as a factor of 10. Both the acetate and propionate were attractive alone, but no synergistic effect was found. trans-Perillenal did not show any behavioral activity. Dental cotton rolls have been used extensively in diprionid pheromone research without knowledge about release rates. The release rate from rolls loaded with different amounts of diprionyl acetate was determined by extracting rolls after different times under constant temperature and wind conditions or after use in field tests. Quantification of diprionyl acetate was done on GC. The release rate was found to be proportional to the amount applied over several orders of magnitude, and persisted for several weeks. Capillaries and rolls with similar release rates caught similar numbers of sawflies.
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| 2. |
- 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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| 3. |
- Hansson, Bill S., et al.
(författare)
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Pheromone variation among eastern European and a western Asian population of the turnip moth Agrotis segetum
- 1990
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Ingår i: Journal of Chemical Ecology. - 0098-0331. ; 16:5, s. 1611-1622
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Tidskriftsartikel (refereegranskat)abstract
- The female sex pheromone composition and the male electro-physiological response with respect to the three main sex pheromone components, (Z)-5-decenyl acetate, (Z)-7-dodecenyl acetate, and (Z)-9-tetradecenyl acetate, were investigated in populations of Agrotis segetum from Armenia and Bulgaria. The percentage composition of the female-produced pheromone was 1:52:47 and 1:42:57 for the respective populations. Corresponding male receptor frequencies were 9:90:1 and 6:92:2. EAG response profiles of the male antennae were similar for the two populations. The populations from Armenia and Bulgaria differed from the earlier investigated French and Swedish populations, which have larger amounts of (Z)-5-decenyl acetate in gland extracts and have a majority of (Z)-5-decenyl acetate-sensitive receptors. Investigation of receptor frequencies on antennae of male Hungarian moths showed that individuals could be classified as either Swedish or Armenian/Bulgarian type. Males of the Swedish type were preferentially attracted to the three-component pheromone blend, whereas blends of (Z)-7-dodecenyl and (Z)-9-tetradecenyl acetate, and (Z)-7-dodecenol [pure or in mixture with (Z)-5-decenol] attracted the Armenian/Bulgarian type. The nature of pheromone variation among European and Asian populations of the turnip moth and possible mechanisms maintaining the variation are discussed.
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| 4. |
- Hansson, B. S., et al.
(författare)
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Sex pheromone perception in male pine sawflies, Neodiprion sertifer (Hymenoptera; Diprionidae)
- 1991
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Ingår i: Journal of Comparative Physiology A: Neuroethology, Sensory, Neural, and Behavioral Physiology. - 0340-7594. ; 168:5, s. 533-538
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Tidskriftsartikel (refereegranskat)abstract
- Electroantennographic and single sensillum recordings were performed on male pine sawfly, Neodiprion sertifer, antennae. Responses to the sex pheromone component (2S, 3S, 7S)- 3,7-dimethyl-2-pentadecenyl (diprionyl) acetate (SSS:OAc), to the behavioral inhibitor (2S, 3R, 7R)-diprionyl acetate (SRR:OAc), to the six other enantiomers of diprionyl acetate, and to the biosynthetic precursor diprionol were recorded. Responses to trans-perillenal, a monoterpene identified in female gland extracts and to (2S, 3S, 7S)-diprionyl propionate (SSS:OPr), a field attractant for N. sertifer and some related sawfly species were also recorded. EAG recordings demonstrated a high antennal sensitivity to SSS:OAc and to SSS:OPr. A somewhat lower response was elicited by SRR:OAc. Single sensillum recordings revealed 8–12 different cells firing in each sensillum, corresponding to the number of cells observed in earlier morphological investigations. Out of these cells all, except one, responded to SSS:OAc and to SSS:OPr. No differences in the response to the two components could be observed. The largest amplitude cell in each sensillum was specifically tuned to the behavioral antagonist, SRR:OAc. The pheromone perception system encountered in male pine sawflies thus differs clearly from that observed in moths.
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| 5. |
- Hedenström, Erik, et al.
(författare)
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Sex Pheromone of pine sawflies. Chiral syntheses of some active minor components isolated from neodiprion sertifer and of some chiral analogues of diprionyl acetate.
- 1992
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Ingår i: Tetrahedron. - 0040-4020. ; 48:15, s. 3139-3146
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Tidskriftsartikel (refereegranskat)abstract
- The chiral syntheses of some analogues, 2 - 7, of 3,7-dimethyl-2-pentadecanol, 1 (diprionol), and of the corresponding acetates are described. The acetate of 1 is the main attractant in the sex pheromone of the Neodiprion genus (Diprionidae). Compounds 2 /2- 4 were identified as minor components isolated from females of Neodiprion sertifer. Synthetic intermediates were prepared either from chiral starting materials, via asymmetric syntheses, or by baker's yeast reductions.
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| 6. |
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| 7. |
- Wassgren, Ann Britt, et al.
(författare)
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Pheromone related compounds in pupal and adult female pine sawflies, Neodiprion sertifer, of different age and in different parts of the body
- 1992
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Ingår i: Journal of Insect Physiology. - 0022-1910. ; 38:11, s. 885-893
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Tidskriftsartikel (refereegranskat)abstract
- The pine sawfly pheromone precursor 3,7-dimethyl-2-pentadecanol (diprionol) was quantified by gas chromatography in different body parts of virgin female Neodiprion sertifer. About one-third of the total amount (approx. 10 ng per female) was found in each of head + thorax, abdominal segments 1-3, and the remaining abdomen. Diprionol was also found in the respective parts of pupae, but in lower amounts. This suggests that at least the final steps of the pheromone biosynthesis take place in many parts of the body, possibly in the cuticle. The diprionol content remained relatively constant over the whole lifetime of virgin females. By using coupled gas chromatography-electroantennogram detection three active compounds in the acetylated female extract were observed. These corresponded to the pheromone, (2S,3S,7S)-diprionyl acetate, and its homologues with the chain shortened by one and two carbons respectively, as determined by gas chromatography-mass spectrometry. In addition, the homologue having a chain elongated by one carbon was found. The homologues occurred in amounts of 2-5% of the diprionyl acetate. When synthetic homologues were tested in the field, alone or in combination with diprionyl acetate, they were not behaviourally active to male sawflies, despite their electroantennogram activity. A threo-isomer of diprionol, most likely (2S,3R,7R), was present in the females in amounts less than 0.5% of the (2S,3S,7S)-content. The acetate of this threo-isomer is known as both synergist and inhibitor to the (2S,3S,7S)-isomer. trans-Perillenal was found in the abdominal segments 1-3 of both males and females and its possible biosynthetic relationship to diprionol is discussed.
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