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1.
  • Anderbrant, Olle, et al. (författare)
  • 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
  • Ingår i: Insects. - : MDPI. - 2075-4450 .- 2075-4450. ; 12:10
  • 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)
  • Attraction of Male Pine Sawflies, Diprion jingyuanensis, to Synthetic Pheromone Candidates: Synergism between Two Stereoisomers
  • 2023
  • Ingår i: Forests. - : MDPI. - 1999-4907. ; 14:6
  • 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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4.
  • Anderbrant, Olle, et al. (författare)
  • Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden
  • 2010
  • Ingår i: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 36:9, s. 969-977
  • 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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6.
  • Anderbrant, Olle, et al. (författare)
  • Geographic variation in the field response of male European pine sawflies, Neodiprion sertifer , to different pheromone stereoisomers and esters
  • 2000
  • Ingår i: Entomologia Experimentalis et Applicata. - : Wiley. - 1570-7458 .- 0013-8703. ; 95:3, s. 229-239
  • 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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10.
  • Anderbrant, Olle, et al. (författare)
  • Pheromone mating disruption of the pine sawfly Neodiprion sertifer : is the size of the treated area important?
  • 2002
  • Ingår i: IOBC/WPRS Bulletin. - 1027-3115. ; 25:9, s. 111-116
  • 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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