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  • 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. - 1573-1561. ; 36, 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.
  • Anderbrant, Olle, et al. (författare)
  • Release of sex pheromone and its precursors in the pine sawfly Diprion pini (Hym., Diprionidae)
  • 2005
  • Ingår i: Chemoecology. - Birkhaüser. - 1423-0445. ; 15:3, s. 147-151
  • 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.
  • Anderbrant, Olle, et al. (författare)
  • Sex Pheromone of the Introduced Pine Sawfly, Diprion similis (Diprionidae), Revisited: No Activity of Earlier Reported Synergists
  • ????
  • Annan publikation (övrigt vetenskapligt)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.
  • Andersson, Fredrik, et al. (författare)
  • Highly stereoselective alkylation of (S)-proline-based chiral auxiliaries
  • 2004
  • Ingår i: Tetrahedron : asymmetry. - 0957-4166. ; 15:16, s. 2539-2545
  • Tidskriftsartikel (refereegranskat)abstract
    • Alkylation of the enolates of the propanoylamides of two chiral auxiliaries (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol 1a and (S)-(-)-2-(2-methoxypropan-2-yl)pyrrolidine 1b, derived from (S)-proline, with benzyl bromide and n-butyl iodide has been studied. The auxiliaries 1a and 1b induced opposite selectivity that is (R)- and (S)-configuration, respectively, at the newly created stereogenic centre. The diastereoselectivities and conversion yields in these alkylations were moderate to excellent. When Cp2ZrCl2 was used as an enolate coordinating agent, benzylation of propanoylated 1b gave an excellent diastereomeric ratio of 99:1. The benzylated diastereomeric products from either propanoylated 1a or 1b were easily separated by liquid chromatography.
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