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E. Hedenström - One of the best experts on this subject based on the ideXlab platform.
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field response of male pine sawflies Neodiprion Sertifer diprionidae to sex pheromone analogs in japan and sweden
Journal of Chemical Ecology, 2010Co-Authors: O. Anderbrant, J. Löfqvist, E. Hedenström, Joakim Bang, Akira Tai, Hans-erik HögbergAbstract: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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Mating disruption of the pine sawfly Neodiprion Sertifer (Hymenoptera: Diprionidae) in isolated pine stands
Agricultural and Forest Entomology, 2002Co-Authors: Antonio Martini, O. Anderbrant, E. Hedenström, N. Baldassari, P. Baronio, Hans-erik Högberg, Gabriella RocchettaAbstract: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. (Less)
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Geographic variation in the field response of male European pine sawflies, Neodiprion Sertifer, to different pheromone stereoisomers and esters
Entomologia Experimentalis et Applicata, 2000Co-Authors: O. Anderbrant, J. Löfqvist, H.-e. Högberg, E. Hedenström, N. Baldassari, P. Baronio, G. Kolmakova, B. Lyons, T. Naito, V. OdinokovAbstract: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 (2 S ,3 S ,7 S )-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 (2 S ,3 R ,7 R )-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 (2 S ,3 R ,7 R )-isomer from Japan and Siberia to Europe. At the eastern sites, increasing amounts of the (2 S ,3 R ,7 R )-isomer up to and equal to the amount of the (2 S ,3 S ,7 S )-isomer, did not influence the trap catch, whereas at sites in Europe, as little as 1% of the (2 S ,3 R ,7 R )-isomer almost completely inhibited the attraction. The response of the North American population was intermediate. The only site in which the (2 S ,3 R ,7 R )-isomer was essential for the attraction of males was in Siberia. A similar pattern was found for the (2 S ,3 R ,7 S )-isomer. Both the acetate and the propionate form of the (2 S ,3 S ,7 S )-isomer were attractive by themselves in Japan, Europe and North America, and neither the (2 S ,3 R ,7 S )-isomer nor the (2 S ,3 R ,7 R )-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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sex pheromone of pine sawflies enantioselective lipase catalysed transesterification of erythro 3 7 dimethylpentadecan 2 ol diprionol
Tetrahedron-asymmetry, 1996Co-Authors: Marten Lundh, Olof Smitt, E. HedenströmAbstract:Abstract (2 S ,3 S ,7 R / S )-3,7-Dimethylpentadecan-2-ol (2S,3S,7R/S)- 1 was prepared with less then 0.5% of (2 R ,3 R ,7 R / S )-3,7-dimethylpentadecan-2-ol via Pseudomonas sp. (PSL) catalysed transesterification of a 1:1:1:1 mixture of the four erythro -3,7-dimethylpentadecan-2-ols and vinyl acetate in n -heptane at initial low water activity (a w S ,3 S ,7 S )-3,7-Dimethylpentadecan-2-ol (Diprionol) is the precursor to the behaviourally active diprionyl acetate used by the female pine sawfly Neodiprion Sertifer as a sexual pheromone. Several lipases, solvents and reaction conditions were tested, and the best results (enantiomeric ratio E = 110) were obtained with Pseudomonas sp. (PSL) and vinyl acetate in iso -octane at initial water activity a w Candida rugosa (CRL, immobilised on polypropylene) as the catalyst in an esterification reaction with rac -4-methyl-dodecanoic acid and eicosanol at a w = 0.8 in cyclohexane a pronounced enantioselectivity was obtained (E = 19).
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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
Journal of Insect Physiology, 1992Co-Authors: Ann-britt Wassgren, O. Anderbrant, J. Löfqvist, E. Hedenström, Bill S. Hansson, Gunnar Bergström, Hans-erik HögbergAbstract: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, (2 S ,3 S ,7 S )-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 (2 S ,3 R ,7 R ), was present in the females in amounts less than 0.5% of the (2 S ,3 S ,7 S )-content. The acetate of this threo -isomer is known as both synergist and inhibitor to the (2 S ,3 S ,7 S )-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.
O. Anderbrant - One of the best experts on this subject based on the ideXlab platform.
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field response of male pine sawflies Neodiprion Sertifer diprionidae to sex pheromone analogs in japan and sweden
Journal of Chemical Ecology, 2010Co-Authors: O. Anderbrant, J. Löfqvist, E. Hedenström, Joakim Bang, Akira Tai, Hans-erik HögbergAbstract: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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Mating disruption of the pine sawfly Neodiprion Sertifer (Hymenoptera: Diprionidae) in isolated pine stands
Agricultural and Forest Entomology, 2002Co-Authors: Antonio Martini, O. Anderbrant, E. Hedenström, N. Baldassari, P. Baronio, Hans-erik Högberg, Gabriella RocchettaAbstract: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. (Less)
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Mating duration and Frequency in a Pine Sawfly
Journal of Insect Behavior, 2001Co-Authors: Fredrik Östrand, O. AnderbrantAbstract:Newly emerged females of the European pine sawfly, Neodiprion Sertifer Geoffroy (Hymenoptera: Diprionidae), were placed on pine twigs in the field and their behavior was recorded. Twenty to 25% of the females attracted wild males and mated on the day of release. One-third to one-half of these females remained and oviposited, while the rest disappeared from their twigs after mating. The mating frequency peaked at noon, and on average the mating lasted for 19 ± 13 (SD) min. Eleven to 30% of the females that remained on their twigs after mating remated, occasionally up to five times. Most released females disappeared from their twigs on the first day. Disappearances included both predation and dispersal. Only a few dispersals >5 m were recorded, because the sawflies were difficult to follow during flight. By color marking, dispersal up to 20 m was recorded.
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Geographic variation in the field response of male European pine sawflies, Neodiprion Sertifer, to different pheromone stereoisomers and esters
Entomologia Experimentalis et Applicata, 2000Co-Authors: O. Anderbrant, J. Löfqvist, H.-e. Högberg, E. Hedenström, N. Baldassari, P. Baronio, G. Kolmakova, B. Lyons, T. Naito, V. OdinokovAbstract: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 (2 S ,3 S ,7 S )-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 (2 S ,3 R ,7 R )-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 (2 S ,3 R ,7 R )-isomer from Japan and Siberia to Europe. At the eastern sites, increasing amounts of the (2 S ,3 R ,7 R )-isomer up to and equal to the amount of the (2 S ,3 S ,7 S )-isomer, did not influence the trap catch, whereas at sites in Europe, as little as 1% of the (2 S ,3 R ,7 R )-isomer almost completely inhibited the attraction. The response of the North American population was intermediate. The only site in which the (2 S ,3 R ,7 R )-isomer was essential for the attraction of males was in Siberia. A similar pattern was found for the (2 S ,3 R ,7 S )-isomer. Both the acetate and the propionate form of the (2 S ,3 S ,7 S )-isomer were attractive by themselves in Japan, Europe and North America, and neither the (2 S ,3 R ,7 S )-isomer nor the (2 S ,3 R ,7 R )-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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Behaviour of male pine sawflies, Neodiprion Sertifer, released downwind from pheromone sources
Entomologia Experimentalis et Applicata, 2000Co-Authors: Fredrik Östrand, O. Anderbrant, Peter JönssonAbstract: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 μg of the sex pheromone, (2 S ,3 S ,7 S )-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.
Anderbrant Olle - One of the best experts on this subject based on the ideXlab platform.
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Monitoring the European pine sawfly with pheromone traps in maturing Scots pine stands
'Wiley', 2006Co-Authors: Lyytikäinen-saarenmaa Päivi, Anderbrant Olle, Hedenström Erik, Varama M, Kukkola M, Kokkonen A M, Högberg Hans-erikAbstract: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 mu g 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 mu g) 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 model-ate defoliation when the seasonal trap catch is 800-1000 males per trap or higher
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From where are insects recruited? A new model to interpret catches of attractive traps
'Wiley', 2003Co-Authors: Östrand Fredrik, Anderbrant OlleAbstract:1 Two new concepts describing the origin of insects caught ill an attractive trap are presented. 2 Male European pine sawflies Neodiprion Sertifer Geoffroy (Hymenoptera: Diprionidae) were marked and released from 50, 100, 200, 400 and 800 m in the four cardinal directions around a centrally placed pheromone trap. 3 Based on linear regression of transformed data, we calculated the seasonal sampling range (r(s)) as 1040 m. 4 We estimated the previously defined 'effective sampling area' (alpha) at 4.9 ha, assuming that the insects are evenly distributed around the trap and that they are attracted from a circular area around it. This is the area from which all insects originate if the trap is 100% effective within the area but captures nothing outside of it. The effective sampling area reveals nothing about the origin of the insects caught. We defined the Cumulative Proportional Catch (CPC) that gives the proportion of the trap catch that originates from an area within a distance r from the trap. At r = r(s) CPC = 1, and in our study 50% of the captured insects originated up to 450 m from the trap. Thus, for the trap used in this study, a relatively large proportion of the catch originates some distance from the trap. 5 We also defined the Catch Concentration (CC), which is the ratio of the radius of the effective sampling area (r(alpha)) to r(s). For our data, CC = 0.12, which is intermediate to high compared to the few other studies that we have extracted information from. If r(alpha) is considerably lower than r(s), then only a small proportion of the insects caught originate from close proximity to the trap. When r(alpha) is close to r(s), the catch adequately mirrors the population within most of its sampling range. 6 By using these two new concepts, we will better understand why monitoring traps mirror the local population in some cases but not in others. This will help in designing more reliable monitoring programmes
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Pheromone mating disruption of the pine sawfly Neodiprion Sertifer : is the size of the treated area important?
Monfavet, 2002Co-Authors: Anderbrant Olle, Hedenström Erik, Högberg Hans-erikAbstract: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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On the origin of pine sawflies caught in pheromone traps
Monfavet, 2002Co-Authors: Östrand Fredrik, Anderbrant OlleAbstract:This study investigated behaviour of male European pine sawflies, Neodiprion Sertifer Geoffr. (Hym., Diprionidae), that were released downwind from pheromone traps. Releases were done at three distances; either at 5 m from one trap, or at 50 m or 200 m from five traps, placed in a line perpendicular to the current wind direction. As a control, males were released identically but without any pheromone source present. The behaviour of the males prior to take-off was studied on a release platform. The following different types of behaviour were recorded: grooming, wing fanning, orientating and take-off. The frequency of grooming was significantly higher in the pheromone treatments compared to the control, whereas the frequency of wing fanning and orientating increased, although not significantly. The direction in which the males displayed the various types of behaviour was more concentrated towards the wind when pheromone was present than during the control experiment. By colour marking of Ecology, Lund University, d travel speed could be calculated. The minimum recorded time from take-off to landing was 1 min, 6 min and 45 min for the 5 m, 50 m and 200 m experiments, respectively. The stimulation and attraction range of the trap was at least 200 m, and the sampling range after 24 hr was calculated to approximately 400 m (c.i. 140–1600 m)
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Mating disruption of the pine sawfly Neodiprion Sertifer (Hymenoptera: Diprionidae) in isolated pine stands
'Wiley', 2002Co-Authors: Martini Antonio, Anderbrant Olle, Hedenström Erik, Högberg Hans-erik, Baldassari Nadia, Baronio Piero, Rocchetta GabriellaAbstract: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
Hans-erik Högberg - One of the best experts on this subject based on the ideXlab platform.
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field response of male pine sawflies Neodiprion Sertifer diprionidae to sex pheromone analogs in japan and sweden
Journal of Chemical Ecology, 2010Co-Authors: O. Anderbrant, J. Löfqvist, E. Hedenström, Joakim Bang, Akira Tai, Hans-erik HögbergAbstract: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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Mating disruption of the pine sawfly Neodiprion Sertifer (Hymenoptera: Diprionidae) in isolated pine stands
Agricultural and Forest Entomology, 2002Co-Authors: Antonio Martini, O. Anderbrant, E. Hedenström, N. Baldassari, P. Baronio, Hans-erik Högberg, Gabriella RocchettaAbstract: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. (Less)
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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
Journal of Insect Physiology, 1992Co-Authors: Ann-britt Wassgren, O. Anderbrant, J. Löfqvist, E. Hedenström, Bill S. Hansson, Gunnar Bergström, Hans-erik HögbergAbstract: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, (2 S ,3 S ,7 S )-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 (2 S ,3 R ,7 R ), was present in the females in amounts less than 0.5% of the (2 S ,3 S ,7 S )-content. The acetate of this threo -isomer is known as both synergist and inhibitor to the (2 S ,3 S ,7 S )-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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Sex Pheromone of pine sawflies. Chiral syntheses of some active minor components isolated from Neodiprion Sertifer and of some chiral analogues of diprionyl acetate.
Tetrahedron, 1992Co-Authors: E. Hedenström, J. Löfqvist, Hans-erik Högberg, Bill S. Hansson, Ann-britt Wassgren, Gunnar Bergström, O. AnderbrantAbstract: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.
Marten Lundh - One of the best experts on this subject based on the ideXlab platform.
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sex pheromone of pine sawflies enantioselective lipase catalysed transesterification of erythro 3 7 dimethylpentadecan 2 ol diprionol
Tetrahedron-asymmetry, 1996Co-Authors: Marten Lundh, Olof Smitt, E. HedenströmAbstract:Abstract (2 S ,3 S ,7 R / S )-3,7-Dimethylpentadecan-2-ol (2S,3S,7R/S)- 1 was prepared with less then 0.5% of (2 R ,3 R ,7 R / S )-3,7-dimethylpentadecan-2-ol via Pseudomonas sp. (PSL) catalysed transesterification of a 1:1:1:1 mixture of the four erythro -3,7-dimethylpentadecan-2-ols and vinyl acetate in n -heptane at initial low water activity (a w S ,3 S ,7 S )-3,7-Dimethylpentadecan-2-ol (Diprionol) is the precursor to the behaviourally active diprionyl acetate used by the female pine sawfly Neodiprion Sertifer as a sexual pheromone. Several lipases, solvents and reaction conditions were tested, and the best results (enantiomeric ratio E = 110) were obtained with Pseudomonas sp. (PSL) and vinyl acetate in iso -octane at initial water activity a w Candida rugosa (CRL, immobilised on polypropylene) as the catalyst in an esterification reaction with rac -4-methyl-dodecanoic acid and eicosanol at a w = 0.8 in cyclohexane a pronounced enantioselectivity was obtained (E = 19).
