| 1. |
- Anderbrant, Olle, et al.
(författare)
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Article sex pheromone of the introduced pine sawfly, diprion similis, revisited to define a useful monitoring lure : Deviating chiral composition and behavioural responses compared to earlier reports
- 2021
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Ingår i: Insects. - : MDPI. - 2075-4450. ; 12:10
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Tidskriftsartikel (refereegranskat)abstract
- Extracts of Diprion similis females contained about 15 ng of the sex pheromone precursor 3,7‐dimethylpentadecan‐2‐ol per female. After derivatisation with (S)‐2‐acetoxypropanoyl chloride, we found that the major stereoisomer in the extract was (2S,3R,7R)‐3,7‐dimethylpentadecan‐2‐ol. Small amounts of other stereoisomers of 3,7‐dimethylpentadecan‐2‐ol were also identified in the extract, namely 1% of (2R,3S,7S), 0.3% (2R,3R,7R) and 0.4% of (2R,3R,7S). An unknown fifth substance showed a very similar spectrum to 3,7‐dimethylpentadecan‐2‐ol, both in SIM and full scan mode. None of the earlier suggested behavioural synergistic isomers ((2S,3S,7S), (2S,3S,7R) and (2S,3R,7S)) were detected in the extracts. In field tests in Ontario, Canada, the earlier identified main pheromone component, viz. the propanoate of (2S,3R,7R)‐3,7‐dimethylpentadecan‐2‐ol, was tested alone and in combination with other stereoisomers, earlier reported to be synergistic. No synergistic effects were detected and the threo four‐isomer blend was as attractive as the pure main compound. Thus, one of the few examples of a diprionid sawfly using more than one substance in its sex pheromone could not be confirmed. The results also suggest that monitoring programs can use the more easily synthesized threo‐blend without losing efficiency. Furthermore, the study suggests that other diprionid pheromones may benefit from a reinvestigation, to clarify possible synergistic effects of stereoisomers.
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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. |
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| 4. |
- Anderbrant, Olle, et al.
(författare)
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Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden
- 2010
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Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 36:9, s. 969-977
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Tidskriftsartikel (refereegranskat)abstract
- The pine sawfly Neodiprion sertifer (Geoffroy) uses the acetate or propionate of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) as pheromone components, with the (2S,3R,7R)-isomer being antagonistic, synergistic, or inactive according to the population tested. In this study, we tested the attraction of males to the acetates of three analogs of diprionol, each missing one methyl group, viz. (2S,7S)-7-methyl-2-pentadecanol, (2S,6S)-2,6-dimethyl-1-tetradecanol, and (2S,3S)-3-methyl-2-pentadecanol. None of the analogs alone, or in combination with diprionol acetate, was attractive in Sweden, even at 100 times the amount of diprionol acetate attractive to N. sertifer. In Japan, the acetate of (2S,3S)-3-methyl-2-pentadecanol attracted males when tested in amounts 10–20 times higher than the acetate pheromone component. The acetate esters of the (2S,3R)-analog and the (2S,3R,7R)-isomer of diprionol also were tested in combination with the pheromone compound (acetate ester). Both compounds caused an almost total trap-catch reduction in Sweden, whereas in Japan they appear to have relatively little effect on trap capture when added to diprionol acetate. Butyrate and iso-butyrate esters of diprionol were unattractive to N. sertifer in Sweden. In summary, there exists geographic variation in N. sertifer in responses to both diprionyl acetate and some of its analogs.
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| 5. |
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| 6. |
- Anderbrant, Olle, et al.
(författare)
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Geographic variation in the field response of male European pine sawflies, Neodiprion sertifer , to different pheromone stereoisomers and esters
- 2000
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Ingår i: Entomologia Experimentalis et Applicata. - : Wiley. - 1570-7458 .- 0013-8703. ; 95:3, s. 229-239
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Tidskriftsartikel (refereegranskat)abstract
- The European pine sawfly, Neodiprion sertifer (Geoffroy) (Hymenoptera: Diprionidae), is a widespread and economically important forest insect. The sex pheromone communication system of this species has been previously investigated in North America, Japan and Europe, with the acetate or propionate of the alcohol (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) shown to be the main pheromone component. In some locations, male attraction either increased or decreased by the addition of the (2S,3R,7R)-diprionyl acetate isomer. However, these studies were made with different batches of synthetic pheromones, with different types of traps and according to different procedures, so the observed differences might not reflect true geographic variation. Here we investigate the geographic pattern of male sawfly response by using identical chemicals, traps and experimental procedures at eight field sites ranging from Japan in the east to Canada in the west. We found an increased inhibitory effect of the (2S,3R,7R)-isomer from Japan and Siberia to Europe. At the eastern sites, increasing amounts of the (2S,3R,7R)-isomer up to and equal to the amount of the (2S,3S,7S )-isomer, did not influence the trap catch, whereas at sites in Europe, as little as 1% of the (2S,3R,7R)-isomer almost completely inhibited the attraction. The response of the North American population was intermediate. The only site in which the (2S,3R,7R)-isomer was essential for the attraction of males was in Siberia. A similar pattern was found for the (2S,3R,7S)-isomer. Both the acetate and the propionate form of the (2S,3S,7S)-isomer were attractive by themselves in Japan, Europe and North America, and neither the (2S,3R,7S)-isomer nor the (2S,3R,7R)-isomer alone were attractive, in the acetate or propionate form. We discuss the significance of our findings for the development of more efficient monitoring schemes and for the causes of population divergence and speciation in the European pine sawfly.
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| 7. |
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| 8. |
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| 9. |
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| 10. |
- Anderbrant, Olle, et al.
(författare)
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Pheromone mating disruption of the pine sawfly Neodiprion sertifer : is the size of the treated area important?
- 2002
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Ingår i: IOBC/WPRS Bulletin. - 1027-3115. ; 25:9, s. 111-116
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Tidskriftsartikel (övrigt vetenskapligt/konstnärligt)abstract
- Few attempts to control forest insects by means of pheromone mating disruption have been reported. The first such experiments with the European pine sawfly, Neodiprion sertifer (Hymenoptera: Diprionidae), resulted in nearly complete trap catch reduction, but no effects on population density or sex ratio were noted. Unmated females lay eggs, which develop into males only. Therefore, if mating disruption would be successful, a more male-biased sex ratio is expected the next generation. One possible explanation for the early results is that mated females disperse into the treated area, and thus obscure the effects of the treatment. In order to reduce the effect of such immigrating females, the treated area was increased in the experiment described here from the earlier used 0.5 – 4 ha to 25 ha. The acetate of erythro-3,7-dimethyl-2- pentadecanol was used for disruption and released from dispensers every 10 m. The influence on male orientation was monitored by pheromone traps, baited with the acetate of (2S,3S,7S)-3,7- dimethyl-2-pentadeanol and placed at 100 m interval along two perpendicular, 1500 m lines intersecting the treated area. The trap catch reduction was near 100% during the first month, but then declined to around 90% during the second month. Mating frequencies were checked by comparing the sex ratio of the next generation from within and outside the treatment area. No effect of the treatment on the sex ratio was detected, and the frequency of mated females could be assumed to be independent of treatment. Alternative hypotheses to explain the failure of pheromone mating disruption in N. sertifer are discussed.
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| 11. |
- 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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| 12. |
- Anderbrant, Olle, et al.
(författare)
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Sex Pheromone of the Introduced Pine Sawfly, Diprion similis (Diprionidae), Revisited: No Activity of Earlier Reported Synergists
-
Annan publikation (övrigt vetenskapligt/konstnärligt)abstract
- Extracts of Diprion similis females were found to contain about 15 ng of the sex pheromone precursor 3,7-dimethylpentadecan-2-ol per female. When analysing the extracts after derivatisation with (2S)-2-acetoxypropionyl chloride, we found that the major stereoisomer in the extract was (2S,3R,7R)-3,7-dimethylpentadecan-2-ol. Also other stereoisomers of 3,7-dimethylpentadecan-2-ol were identified in the extract namely, 1% of (2R,3S,7S) , 0.3% (2R,3R,7R) and 0.4% of (2R,3R,7S). An unknown fifth substance showed an identical spectrum to 3,7-dimethylpentadecan-2-ol, both in SIM and full scan mode. In field tests in Ontario, Canada, the earlier identified main pheromone component, viz. the propanoate of (2S,3R,7R)-3,7-dimethylpentadecan-2-ol, was tested alone and in combination with other stereoisomers, earlier reported to be synergistic. In none of the tests were any synergistic effects detected and the threo four-isomer blend was as attractive as the pure main compound. Thus, one of the few examples of a diprionid sawfly using more than one substance in its sex pheromone could not be confirmed. The results also suggest that monitoring programs can use the more easily synthesized threo-blend without losing efficiency.
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| 13. |
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| 14. |
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| 15. |
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| 16. |
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| 17. |
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| 18. |
- Bång, Joakim
(författare)
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Purification, Stereoisomeric Analysis and Quantification of Biologically Active Compounds in Extracts from Pine Sawflies, African Butterflies and Orchid Bees
- 2011
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Doktorsavhandling (övrigt vetenskapligt/konstnärligt)abstract
- Stereochemistry plays an important role in nature because biologically important molecules such as amino acids, nucleotides and sugars, only exist in enantiomerically pure forms. Semiochemicals carry messages, between the same species (pheromones) and between different species (allelochemicals). Both pheromones and allelochemicals can be used as environmentally friendly pest management. Many semiochemicals, i.e. behaviour modifying chemicals, consist of pure or well-defined mixtures of stereoisomers, where some of the other stereoisomers can be repellent. It is therefore important to be able to separate them to produce a synthetic pheromone in a mixture that is attractive.Pine sawflies are a family of insects that in some cases can be severe defoliators of conifer trees. Diprion pini, Diprion similis and Neodiprion sertifer are severe pests for these trees and have got the most attention in pine sawfly pheromone studies. The pheromone precursors are stored in the female body as long-chain secondary alcohols, which, when released, are esterified to acetates or propionates. The alcohols are chiral, and normally one of the stereoisomer is the main pheromone component, sometimes possible together with other stereoisomers as essential minor components.Bicyclus is a genus of African butterflies, and especially Bicyclus anynana has become a popular model for the study of life history evolution, morphology, mating choice and genetics. The wing pattern of Bicyclus differs depending on the season, with large eyespots during the rain-season and small or absent spots during the dry season. Euglossa is one of the genera among the orchid bees in the Neotropics that does not produce its own pheromone. Instead, the males collect fragrances from orchids and other sources and store them in a pocket in their hind legs. Both Bicyclus and Euglossa use semiochemicals similar to pine sawflies, and thus can be analysed by the same methods.Pheromones and other semiochemicals in insects are often present in low amounts in a complex matrix, and purification of the sample before chemical analysis is often required. A common method is gradient elution on a solid phase silica column. Separation of stereoisomers can be achieved either by using a column with a chiral stationary phase (CSP) or with pre-column derivatisation using a column with an achiral stationary phase (ASP) or a combination of both, with mass detection as the dominant detection method. The purpose of this work has been to improve the purification method, find suitable methods to separate the stereoisomers of secondary alcohols, and to apply this on extracts of insects.By selecting the right fractions to collect during gradient elution the purification method was optimised. To reduce plasticizer contamination from ordinary columns, solid phase columns of Teflon or glass were used. For pre-column derivatisation of different chiral alcohols various acid chlorides were tested. For the pine sawfly pheromone precursors enantiopure (2S)-2-acetoxypropionyl chloride was the best choice. To separate some of the stereoisomers achiral 2-naphthoyl chloride was used. For derivatisation of 6,10,14-trimethylpentadecan-2-ol (R)-trans-chrysanthemoyl chloride was the best choice. The derivatised alcohols were separated on different columns, both chiral and non-chiral. Varian FactorFour VF-23ms was chosen as a general-purpose column, the Agilent HP-88 column was the best column with an ASP of those tested, and the Chiraldex B-PA column (CSP) was the only one that could separate all eight stereoisomers of derivatised 3,7-dimethylundecan-2-ol, 3,7-dimethyldodecan-2-ol, and 3,7-dimethyltridecan-2-ol.To determine the stereoisomeric purity of standard solutions used in field experiments and extracts of different species of insects the optimised methods were applied. For extracts from B. anynana, Euglossa and Neodiprion lecontei this work describe the first determination of the stereochemistry of some of their semiochemicals.For the determination of the stereochemistry of chiral semiochemicals the methods for purification and separation presented herein have shown to be of great value. The results will hopefully contribute to a better understanding of the communication among insects, and ultimately to a more environmentally friendly pest control.
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| 19. |
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| 20. |
- 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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| 21. |
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| 22. |
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| 23. |
- 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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| 24. |
- Holmberg, Erland, et al.
(författare)
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Reaction conditions for the resolution of 2-methylalkanoic acids in esterification and hydrolysis with lipase from Candida cylindracea
- 1991
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Ingår i: Applied Microbiology and Biotechnology. - 0175-7598. ; 35:5, s. 572-578
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Tidskriftsartikel (refereegranskat)abstract
- We have demonstrated resolution of 2-methylalkanoic acids using lipase from Candida cylindracea as a catalyst. The resolution of 2-methyldecanoic acid was more successful than that of 2-methylbutyric acid both by esterification and hydrolysis. This indicates that the resolution of the acid is dependent on the chain length of the acid moiety. The chain length of the alcohol moiety of the ester affected the resolution of the long-chain acid only. Using esterification, (R)-2-methyldecanoic acid was produced in an enantiomeric excess (e.e.) of 95% (E = 40). If the enantiomeric ratio is low (E = 3.6), as in the resolution of 2-methylbutyric acid, esterification combined with a high equilibrium conversion could be used to yield the remaining acid in a high e.e. In the hydrolytic reactions, the e.e. and the equilibrium conversion were dependent on the pH and the presence of CaCl2. When octyl 2-methyldecanoate was hydrolysed at pH 8.0 in the presence of CaCl2, the (S)-acid was formed with an e.e. of 80% (E = 9), but when the hydrolysis was carried out at pH 7.5 without CaCl2, a very low e.e. and a low equilibrium conversion were observed. The latter conditions allowed the esterification of 2-methyldecanoic acid with 1-octanol even in aqueous medium.
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| 25. |
- Högberg, Hans-Erik, et al.
(författare)
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Biocatalysis as a useful tool in pheromone synthesis. Enantiomerically pure building blocks from baker's yeast reductions and enzyme catalysed resoluti
- 1994
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Ingår i: Catalysis Today. - : Elsevier BV. - 0920-5861. ; 22:3, s. 591-606
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Tidskriftsartikel (refereegranskat)abstract
- Biocatalytical methods are presented which provide useful building blocks for pheromone synthesis. Examples of the utility of this approach are the preparation of building blocks for the synthesis of stereochemically pure isomers of pine sawfly pheromones and some other pheromones. Enantiom- erically pure ( 98% ee) 2-methyl-1-alkanols 2 were obtained via baker's yeast reduction of suitable α,β-unsaturated aldehydes, and by using lipases from Pseudomonas to effect resolution by transesterification of suitable racemic precursors to 2-methyl-1-alkanols 2 which gave high enantiomeric ratios E > 100. The resolution by esterification mediated by lipase from Candida rugosa of racemic 2-methylalkanoic acids also gave high enantiomeric ratios E> 100 after having improved the reaction conditions by regulating water activity, by choice of the appropriate complimentary substrate alcohol and by adjusting the initial equivalents of the latter present at the start. Also discussed is the separation of diastereomers of diprionol 1, which is naturally occurring in the pine sawfly Neodiprion sertifer, where it is the direct precursor of its pheromone.
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| 26. |
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| 27. |
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| 28. |
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| 29. |
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| 30. |
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| 31. |
- Johansson, Björn, et al.
(författare)
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Release Rates for Pine Sawfly Pheromones from Two Types of Dispensers and Phenology of Neodiprion sertifer
- 2001
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Ingår i: Journal of Chemical Ecology. - 0098-0331 .- 1573-1561. ; 27:4, s. 733-745
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Tidskriftsartikel (refereegranskat)abstract
- Comparisons of release rates, duration in the field, and catch efficiency of polyethylene and cotton roll dispensers for the sex pheromones of sawflies (Hymenoptera: Diprionidae) were conducted. The release rates of the Neodiprion sertifer (Geoffr.) and Diprion pini (L.) sex pheromones, the acetates of pentadecanol and (2S,3S,7S)-3,7-dimethyl (2S,3R,7R)-3,7-dimethyl-2-tridecanol from polyethylene dispensers were measured at different temperatures in the laboratory. The release rates for the substances depended on both the temperature and initial load in the vials. The catch from cotton rolls baited with 100 μg of the acetate or propionate of 3,7-dimethyl-2-pentadecanol was compared to the catch from regularly renewed cotton rolls baited with 10 μg of the same acetate. The catch was higher for the 100-μg cotton rolls for, at most, 45 days, and there was no significant difference in catch between the acetate and the propionate. The catch in traps baited with polyethylene or cotton roll dispensers loaded with the acetate of 3,7-dimethyl-2-pentadecanol was compared and showed that cotton roll traps mirrored the decreasing release of the substance rather than the actual flight activity. The length of the flight period of N. sertifer in Sweden, the Czech Republic, Italy, and Greece did not exceed 100 days in any of the countries. By adjusting the initial pheromone load of the polyethylene vials to the expected temperatures, it should be possible to get a constant and sufficiently high release rate during the entire flight period.
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| 32. |
- Larsson, Michael, et al.
(författare)
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Syntheses of the sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol, including the (2S,3S,7S,11R) and (2S,3S,7S,11S) stereoisomers identified as pheromone precursors in females of the pine sawfly Microdiprion pallipes (Hymenoptera : Diprionidae). : Diprionidae)
- 2001
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Ingår i: European Journal of Organic Chemistry. - 1434-193X .- 1099-0690. ; :2, s. 353-363
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Tidskriftsartikel (refereegranskat)abstract
- All sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol were synthesised in high stereoisomerical purities (> 95%), for use in the identification of the stereoisomers present in females of the pine sawfly Microdiprion pallipes (Fallen) (Hymenoptera: Diprionidae) as the precursor of the actual sex pheromone (which is the propionate), and also for investigation of the biological activities of the esters. The key step in the syntheses was the coupling of each of the enantiomers of cis-3,4-dimethyl-gamma -butyrolactone with each of the four pure stereoisomers of 1-lithio-2,6-dimethyloctanes. The four corresponding alcohols were obtained by lipase-catalysed (Amano PS) kinetic separation, based on selective acylation of either (2R/S,6S)- or (2R/S,GR)-2,6-dimethyl-1-octanol (obtained from the optically pure enantiomers of citronellal). Additionally, a mixture of the 16 possible stereoisomers of 3,7,11-trimethyl-2-tridecanol was also prepared.
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| 33. |
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| 34. |
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| 35. |
- Lyytikäinen-Saarenmaa, Päivi, et al.
(författare)
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Monitoring European pine sawfly population densities with pheromone traps in young pine plantations
- 1999
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Ingår i: Forest Ecology and Management. - 0378-1127. ; 124:2-3, s. 113-121
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Tidskriftsartikel (refereegranskat)abstract
- Field trials utilizing pheromone traps were evaluated to develop a population monitoring and predicting system for the European pine sawfly (Neodiprion sertifer). Larval density was censused in a transect across each study site. Three traps per site were baited with 100μg of (2S,3S,7S)-3,7-dimethyl-2-pentadecyl (diprionyl) acetate. During a two-year period traps loaded with 1, 10 and 100 μg of diprionyl acetate were compared. Correlations and coefficients of determination between numbers of captured males and larvae of the same or successive generations were seldom high. Between-generation relationships were significant, when population density was increasing. Having years with increasing densities in a row, the present monitoring method might provide warning of an outbreak.
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| 36. |
- Lyytikäinen-Saarenmaa, P, et al.
(författare)
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Monitoring the European pine sawfly with pheromone traps in maturing Scots pine stands
- 2006
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Ingår i: Agricultural and Forest Entomology. - : Wiley. - 1461-9555 .- 1461-9563. ; 8:1, s. 7-15
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Tidskriftsartikel (refereegranskat)abstract
- 1. During 1989-93, field studies were conducted in Finland to develop a method based on pheromone traps to monitor and forecast population levels of the European pine sawfly (Neodiprion sertifer Geoffr.) and tree defoliation. 2. Three traps per site were baited with 100 μg of the N. sertifer sex pheromone, the acetate ester of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol), in maturing pine stands in southern and central Finland. In addition, three different dosages (1, 10 and 100 μg) of the pheromone were tested in 1991-92. 3. The highest number of males was observed in traps baited with the highest dose. On average, there was a 10-fold increase in trap catch between lure doses. 4. Density of overwintering eggs was used to evaluate the effectiveness of pheromone traps in predicting sawfly populations. The proportion of healthy overwintering eggs was determined each year. A model based on the number of current shoots on sample trees, diameter at breast height and tree height was formulated to estimate eggs per hectare. 5. Linear regression analysis produced high coefficients of determination between number of males in traps and density of total eggs in the subsequent generation, when populations were at peak densities. The relationships were not significant for low population densities. The results indicate a risk of moderate defoliation when the seasonal trap catch is 800-1000 males per trap or higher.
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| 37. |
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| 38. |
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| 39. |
- Lyytikäinen-Saarenmaa, Päivi, et al.
(författare)
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Predicting pine sawfly population densities and subsequent defoliation with pheromone traps
- 2001
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Ingår i: INTEGRATED MANAGEMENT AND DYNAMICS OF FOREST DEFOILIATING INSECTS, PROCEEDINGS. ; 277, s. 108-116
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Konferensbidrag (övrigt vetenskapligt/konstnärligt)abstract
- Field in Finland to develop a monitoring and prediction trials were conducted from 1989 to 1993 method using pheromone traps for European pine sawfly (Neadiprion sertifer Geoffr.) population densities and needle defoliation. Three traps per site were baited with 100 mug of(2S,3S,7S) - 3,7 - dimethyl - 2 - pentadecyl acetate (diprionyl) at sites representing advanced pine stands. The number of overwintering eggs per sample branch was used to evaluate the effectiveness of using pheromone traps to estimate sawfly populations. The relationships between the number of males in traps, the number of eggs per branch in the subsequent generation, and the number of needle-year classes after the subsequent growing season were highly correlated. The risk threshold for moderate to heavy defoliation was around 1,000 males/trap. Our results suggest that after some minor improvements, a pheromone-based monitoring system for the European pine sawfly would provide an effective tool for integrated pest management programs and successful forest management in coniferous pine-dominated forests.
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| 40. |
- Martini, A., et al.
(författare)
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Mating disruption of the pine sawfly Neodiprion sertifer (Hymenoptera. Diprionidae) in isolated pine stands
- 2002
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Ingår i: Agricultural and Forest Enthomology. - : Wiley. - 1461-9555 .- 1461-9563. ; 4:3, s. 195-201
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Tidskriftsartikel (refereegranskat)abstract
- 1. Previous applications of the mating disruption technique to Neodiprion sertifer resulted in decreased numbers of males caught in the treated area but no effect on sex ratio or overall population density. 2. The present study assessed the efficacy of mating disruption against N. sertifer outbreaks in pine stands surrounded by agricultural areas or pasture, and therefore isolated from other infested areas. 3. Pine stands were treated by placing dispensers with an erythro-mixture of the acetate ester of 3,7-dimethyl-2-pentadecanol every 10 m in a grid. 4. The efficacy of this technique was evaluated by comparing the number of males caught in sticky traps baited with synthetic pheromone, and by comparing the sex ratio and the population density of the sawfly in the subsequent generation between treated and control pine stands. 5. The number of males caught within treated areas was significantly lower than in the control area. 6. In the treated pine stands 46% of the egg clusters resulted in male cocoons only, compared to 3% of the clusters in the control stand. 7. A significant reduction of the sawfly population was observed in the treated pine stands. The results contrast to the earlier mating disruption attempts with N. sertifer and can probably be ascribed to the isolation of the experimental stands.
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| 41. |
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| 42. |
- Nordin, Ove, et al.
(författare)
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Kinetic Resolution of Primary 2-methylalcohols via Pseudomonas cepacia Lipase Catalysed Enantioselective Acylation
- 2000
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Ingår i: Journal of The Chemical Society. Perkin Transactions 1. - : Royal Society of Chemistry (RSC). - 1472-7781 .- 1470-4358 .- 1364-5463. ; , s. 367-376
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Tidskriftsartikel (refereegranskat)abstract
- The enantioselectivities of lipases from Pseudomonas cepacia (PFL, Amano PS, etc.) towards a series of primary 2-methyl-substituted alcohols using vinyl acetate as the acyl donor in transesterifications in organic solvents were studied. In terms of enantioselectivity, the best results were found for 3-aryl-2-methylpropan-1-ols with enantiomeric ratios (E-values) over 100 in most cases, whereas other 3-substituted primary 2-methylpropan-1-ols generally displayed lower enantioselectivities: 3-cycloalkyl-2-methylpropan-1-ols (E ≈ 20) and 2-methylalkan-1-ols (E ≈ 10). Moving the aryl group closer or further away from the chiral centre resulted in low enantioselectivities: 2-arylpropan-1-ols (E < 10), 2-methyl-4-(2-thienyl)butan-l-ol (E = 12), 2-methyl-5-(2-thienyl)pentan-l-ol (E=3.2) and 2-methyl-6-(2-thienyl)hexan-l-ol (E=3.8).
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| 43. |
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| 44. |
- Rieske, LK, et al.
(författare)
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Captures of male European pine sawflies (Hymenoptera : Diprionidae) in pheromone-baited traps in Kentucky
- 2001
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Ingår i: Journal of Entomological Science. - 0749-8004. ; 36:1, s. 67-73
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Tidskriftsartikel (refereegranskat)abstract
- Using sticky traps baited with (2S, 3S, 7S)-3,7-dimethyl-2-pentadecyl acetate, we assessed the seasonal and diurnal flight activity of the European pine sawfly, Neodiprion sertifer (Geoffrey), in Fayette, Madison, and Livingston counties in Kentucky. At each site, two replicates of individual sticky traps were baited and suspended about 1 m high and spaced at least 20 m apart. Trap catch was affected by site (P = 0.001). A total of 326 European pine sawfly males were captured at the Fayette Co. site during the period 18 September to 12 November, representing 7% of the season total. No males of this species were caught at the other sites. During peak flight activity (1 to 15 October), we monitored traps at 2.5-h intervals over 4 d to determine diurnal flight patterns. Flight activity began after 1100 h and ceased by 1830 h, and was significantly affected by time of day. European pine sawfly flight activity was greatest between 1330 and 1330 h. We captured over 5,200 male sawflies at all three sites, with peak activity occurring in May, July, September and October.
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| 45. |
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| 46. |
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| 47. |
- 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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| 48. |
- 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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| 49. |
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| 50. |
- Östrand, Fredrik, et al.
(författare)
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Stereoisomeric composition of the sex pheromone of the pine sawfly Microdiprion pallipes (Hym., Diprionidae)
- 2003
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Ingår i: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 13:3, s. 155-162
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Tidskriftsartikel (refereegranskat)abstract
- The basic chemical structure of the sex pheromone of the pine sawfly Microdiprion pallipes (Fallen) has earlier been identified as the propionate ester of (2S,3S,7 R/S,11 R/S)/(2R,3R,7 R/S,11 R/S)-3,7,11-trimethyl-2-tridecanol. We now report the results from further investigations on the male response to individual stereoisomers and to blends of stereoisomers, both in electroantennographic (EAG) recordings and in field trapping experiments. We also present our attempts to determine the stereochemistry of the compounds present in females of M. pallipes. By comparing gas chromatograms and mass spectra obtained from natural extracts with those from synthetic compounds it was found that the females contain one or more of the four (2S,3S,7 R/S,11 R/S)-3,7,11-trimethyl-2-tridecanol isomers (SS++-1). The active pheromone component is the corresponding propionate ester 2. In EAG experiments, males responded most strongly to five propionate ester samples, namely two four-isomer blends: SS++-2 and SR++-2, and three individual stereoisomers: SSSR-, SRRR- and SRSR-2. In a series of field trapping experiments it was found that males were attracted to the SR++-2 four-isomer blend and to the individual isomer SSSR-2. Based on the EAG-recordings and field responses of males and the stereoisomers found in the females, we suggest that the propionate ester of (2S,3S,7S,11R)-3,7,11-trimethyl-2-tridecanol (SSSR-2) is used as a main component of the sex pheromone in M. pallipes. Apparently the males react to other stereoisomers in addition to that or those produced by the females.
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