| 1. |
- Steinbauer, Martin J, et al.
(författare)
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Identification, synthesis and activity of sex pheromone gland components of the autumn gum moth (Lepidoptera: Geometridae), a defoliator of Eucalyptus
- 2004
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Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 14:3-4, s. 217-223
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Tidskriftsartikel (refereegranskat)abstract
- The autumn gum moth, Mnesampela privata (Guenee) (Lepidoptera: Geometridae), is native to Australia and can be a pest of plantation eucalypts. Field-collected and laboratory-reared female autumn gum moths were dissected to remove glands likely to contain components of the sex pheromone. Using gas chromatography (GC) and combined gas chromatography-mass spectrometry (GC-MS), three compounds were identified from female extracts, namely (3Z,6Z,9Z)-3,6,9-nonadecatriene, 1-hexadecanol and 1-octadecanol (confirmed by comparison with synthetic samples). Nonadecatriene elicited an antennal response in male autumn gum moth during gas chromatographic analyses combined with electroantennographic detection (GC-EAD). In electroantennogram (EAG) recording male M. privata antennae responded to the nonadecatriene. Nonadecatriene was synthesised via Kolbe electrolysis, starting with (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid (linolenic acid) and propanoic acid or via an alternative four-step method also starting from linolenic acid. In field trials (3Z,6Z,9Z)-3,6,9-nonadecatriene proved attractive to male moths. Thus, we conclude that (3Z,6Z,9Z)-3,6,9-nonadecatriene is a sex pheromone component of autumn gum moth. This component has been identified in extracts from other geometrids in the same subfamily, Ennominae. However, to our knowledge this is the first example where (3Z,6Z,9Z)-3,6,9-nonadecatriene has been found in females and also proved attractive to male moths when presented on its own. Our results are discussed in relation to other geometrid pheromones.
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| 2. |
- Anderbrant, Olle, et al.
(författare)
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Attraction of Male Pine Sawflies, Diprion jingyuanensis, to Synthetic Pheromone Candidates: Synergism between Two Stereoisomers
- 2023
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Ingår i: Forests. - : MDPI. - 1999-4907. ; 14:6
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Tidskriftsartikel (refereegranskat)abstract
- The pine sawfly Diprion jingyuanensis Xiao and Zhang (Hymenoptera: Diprionidae) is a serious pest of Pinus tabulaeformis Carr. in the Shanxi, Gansu, and Inner Mongolia provinces in P. R. China. The sex pheromone of D. jingyuanensis was shown to be the propionate ester of 3,7-dimethyl-2-tridecanol. Virgin females contained an approximate 1:3 blend of the pheromone precursors erythro-(2S,3S,7R/S and 2R,3R,7R/S)-3,7-dimethyl-2-tridecanol and threo-(2S,3R,7R/S and 2R,3S,7R/S)-3,7-dimethyl-2-tridecanol, but the exact stereoisomers were not determined. Males responded the strongest to the propionate ester of the two threo-isomers, (2S,3R,7R) and (2S,3R,7S), in electroantennogram (EAG) recordings, followed by a significant EAG response to the (2S,3R,7R) propionate of diprionol (pheromone component of D. similis), whereas the remaining two isomers (2S,3S,7S and 2S,3S,7R) of the propionate ester of 3,7-dimethyl-2-tridecanol and the acetate of the (2S,3R,7R) isomer (one of the two pheromone components of D. pini) did not elicit any significant increase in antennal response. In the field, the strongly EAG-active (2S,3R,7R)-isomer alone was only weakly (but significantly) attractive to D. jingyuanensis males at 100 & mu;g, while the equally EAG- active (2S,3R,7S)-isomer alone at the same loading was 8-14 times more attractive than was the (2S,3R,7R)-isomer alone. Traps baited with the same amounts of the two threo-isomers ((2S,3R,7R) and (2S,3R,7S), 100 & mu;g + 100 & mu;g) caught significantly more males than did traps baited with other isomers, either of the two isomers alone or other proportions of the two isomers. Thus, the (2S,3R,7S)-isomer is considered as a strong and essential sex-attractant component for D. jingyuanensis males, whereas the (2S,3R,7R)-isomer is a weak but synergistic sex-attractant. This is one of the few examples of a pine sawfly responding significantly stronger to a binary blend of stereoisomers in a synergistic fashion than to a single stereoisomer alone.
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| 3. |
- Anderbrant, Olle, et al.
(författare)
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Release of sex pheromone and its precursors in the pine sawfly Diprion pini (Hym., Diprionidae)
- 2005
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Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 15:3, s. 147-151
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Tidskriftsartikel (refereegranskat)abstract
- The first identification of a sex pheromone of a pine sawfly (Hymenoptera, Diprionidae) dates back almost thirty years. Since then, female-produced pheromones of over twenty diprionid species have been investigated by solvent extraction followed by separation and identification. However, no study has shown what the females actually release. Collection of airborne compounds using absorbtion on charcoal filter as well as solid phase microextraction (SPME) followed by analysis employing gas chromatography combined with mass spectrometry (GC-MS), revealed an unusual system in Diprion pini, in which the pheromone precursor alcohol, 3,7-dimethyl-2-tridecanol, is released together with acetic, propionic, butyric and isobutyric acids. The corresponding acetate, propionate and butyrate esters of 3,7-dimethyl-2-tridecanol were also found in the samples. All esters were electrophysiologically active, and the propionate and isobutyrate were attractive in trapping experiments. Based on these and earlier reported results, it seems that at least in part of its range, the pheromone response of D. pini is not very specific with regard to the functional group, as long as this is an ester.
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| 4. |
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| 5. |
- Brodin, Yngve, et al.
(författare)
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Tvåvingar Diptera
- 2020
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Ingår i: Rödlistade arter i Sverige 2020 – The 2020 Red List of Swedish Species. - 9789187853548 ; , s. 133-140
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Bokkapitel (övrigt vetenskapligt/konstnärligt)
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| 6. |
- Brodin, Yngve, et al.
(författare)
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Tvåvingar Diptera
- 2015
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Ingår i: Rödlistade arter i Sverige 2015. - 9789187853104 ; , s. 113-118
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Bokkapitel (övrigt vetenskapligt/konstnärligt)
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| 7. |
- Hedenström, Erik, et al.
(författare)
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Sex pheromone of the pine sawfly, Gilpinia pallida: Chemical identification, synthesis, and biological activity
- 2006
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 32:11, s. 2525-2541
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Tidskriftsartikel (refereegranskat)abstract
- We present the identification of the sex pheromone in the pine sawfly, Gilpinia pallida, including analysis of the female pheromone content, male antennal response and attraction in the field, and synthesis of the most active pheromone component. Several 3,7-dimethyl-2-alkanols were identified from female whole-body extracts, including some compounds with a 2R configuration. This is the first observation of such compounds in a pine sawfly species. Antennae of male G. pallida responded strongly in electroantennograph (EAG) recordings to the (2S,3R,7R)-isomers of the propionates of 3,7-dimethyl-2-tridecanol, 3,7-dimethyl-2-tetradecanol, and 3,7-dimethyl-2-pentadecanol, as well as to the acetates of the tri- and pentadecanols (the acetate of the tetradecanol was not tested). The propionate of (2S,3R,7R)-3,7-dimethyl-2-tetradecanol caught more males in the field than the corresponding isomer of tri- or pentadecanol. We suggest that the (2S,3R,7R)-isomer of 3,7-dimethyl-2-tetradecanol is likely the main sex pheromone precursor in G. pallida, with a subsidiary role for the (2S,3R,7R)-isomer of the tridecanol. Preparation of highly pure (2R,3R,7R)- and (2S,3R,7R)-stereoisomers of 3,7-dimethyl-2-tetradecanol, including the biological active esters, was performed via chemoenzymatic methods and is described in detail.
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| 8. |
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| 9. |
- Wallander, Håkan, et al.
(författare)
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Uptake of N-15-labelled alanine, ammonium and nitrate in Pinus sylvestris L. Ectomycorrhiza growing in forest soil treated with nitrogen, sulphur or lime
- 1997
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Ingår i: Plant and Soil. - 0032-079X. ; 195:2, s. 329-338
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Tidskriftsartikel (refereegranskat)abstract
- The uptake of N-15-labelled alanine, ammonium and nitrate was studied in ectomycorrhizal morphotypes of intact Pinus sylvestris seedlings. PCR-RFLP analysis of the ITS-region of fungal rDNA was used to identify the morphotypes. Seedlings were grown in forest soil collected at an experimental site in southern Sweden. The treatments compared were a control, N fertilisation (600 kg N ha(-1) as urea), sulfur application (1200 kg S ha(-1)) and lime application (6000 kg CaCO3 ha(-1)). The forest, which had been dominated by Picea abies, was clear-cut two years before the forest soil was sampled. Soil was also collected from an adjacent standing forest. The aim of the present study was to detect changes in the ectomycorrhizal communities in forest soils and relate these changes to the functional parameter of uptake of nitrogen from organic (alanine and protein) and inorganic (ammonium and nitrate) sources. Liming resulted in the detection of a morphotype not found in other samples, and one morphotype was only found in samples from the standing forest (the fungi in these two morphotypes could not be identified). All mycorrhizal root tips showed a higher N-15 concentration after exposure to different nitrogen forms than non-mycorrhizal long roots. Uptake of N-15 from a labelled solution of alanine or ammonium was higher (about tenfold) than uptake from a N-15-labelled solution of nitrate. Uptake of ammonium and alanine varied between 0.2 and 0.5 mg N g(-1) h(-1) and between 0.1 and 0.33 mg N g(-1) h(-1), respectively, among the different morphotypes. In seedlings grown in the control soil and in soil from standing forest, alanine and ammonium were taken up to a similar degree from a supply solution by all morphotypes, whereas ammonium uptake was higher than alanine uptake in seedlings grown in lime-treated soil (about twofold) and. to a lesser extent, in the nitrogen-and sulfur-treated soils. The higher ammonium uptake by morphotypes from the limed soil was confirmed in pure culture studies. In cases where ammonium was used as the N source, an isolate of the S. variegatus morphotype collected in the limed soil produced more biomass compared with isolates of S. variegatus collected in nitrogen or sulphur-treated soil. One isolate of a silvery white morphotype produced about equal amounts of biomass on alanine and ammonium, whereas all S. variegatus isolated performed better with ammonium as their N source. Based on the results it is hypothesised that liming can induce a shift in the ectomycorrhizal community, favouring individuals that mainly utilise inorganic nitrogen over those that primarily utilise organic nitrogen
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| 10. |
- Östrand, Fredrik, et al.
(författare)
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Behaviour of male pine sawflies, Neodiprion sertifer , released downwind from pheromone sources
- 2000
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Ingår i: Entomologia Experimentalis et Applicata. - : Wiley. - 1570-7458 .- 0013-8703. ; 95:2, s. 119-128
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Tidskriftsartikel (refereegranskat)abstract
- This study investigated the behaviour of male European pine sawflies, Neodiprion sertifer Geoffroy (Hym., Diprionidae), that were released and observed downwind from pheromone traps baited with 100 mu g of the sex pheromone, (2S,3S,7S)-3,7-dimethyl-2-pentadecyl acetate. Releases were done at three distances; either at 5 m from one trap, or at 50 or 200 m from five traps, placed in a line perpendicular to the current wind direction. As control, males were released identically but without any pheromone source present. The behaviour of the males prior to take-off was studied. A total of 1729 males were released, and 80% of them took flight. Males took off significantly faster in the presence of pheromone. Grooming was significantly more frequent in presence of pheromone compared with control. In all pheromone experiments significantly more males displayed grooming, wing fanning and take-off towards the wind compared with the control. Weather data was simultaneously collected at the study site. Wing fanning was negatively correlated with wind speed. Grooming was not influenced by wind speed. Reduced levels of incoming short-wave radiation lowered the take-off frequency significantly. Pheromone-induced behaviour in diprionids seems to be less distinct than in other insects, e.g., Lepidoptera.
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