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  • 1.
    Bång, Joakim
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Hedenström, Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Purification, Stereoisomeric Analysis and Quantification of Sex Pheromone Precursors in Female Whole Body Extracts from Pine Sawfly Species2011In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 37, no 1, p. 125-133Article in journal (Refereed)
    Abstract [en]

    A GC-MS method to analyze the stereoisomeric composition of chiral secondary alcohols found in whole body extracts of pine sawfly females was developed. The tested alcohols were derivatized with optically pure (S)-2-acetoxypropionyl chloride prior to GC-MS analysis. Baseline separation was obtained for all sixteen stereoisomers of 3,7,9-trimethyltridecan-2-ol and for the four 3-methylpentadecan-2-ol stereoisomers. For 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol and 3,7-dimethylpentadecan-2-ol baseline separation was obtained for 6 of the possible 8 stereoisomers. When a mixture of 16 stereoisomers of 3,7,11-trimethyltridecan-2-ol was tested, baseline separation of 7 peaks out of 16 possible was obtained. The investigated alcohols are pheromone precursors for some pine sawfly species that are severe defoliators of pine. Females from several Diprion, Neodiprion, Macrodiprion, Microdiprion, and Gilpinia species emit esters of such secondary alcohols as sex pheromones that attract males for mating. To quantify the small amounts of the precursor alcohol and its stereoisomeric composition found in whole body extracts from female pine sawflies, a purification method was optimized. An extract of 20 females of D. pini contained about 8 ng of (2 S,3 R,7 R)-3,7-dimethyltridecan-2-ol per female, and three extracts of 18, 20, and 90 females of N. sertifer contained between 5 and 13 ng of (2 S,3 S,7 S)-3,7-dimethylpentadecan-2-ol per female.

  • 2.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Månsson, Per
    Schlyter, Fredrik
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Strategier i sökandet efter gnaghämmare mot snytbaggen, Hylobius abietis: Föredrag, 19:e Organikerdagarna i Linköpng 20042004Conference paper (Other academic)
  • 3.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Månsson, P. E.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Schlyter, F
    Antifeedants and feeding stimulants in bark extracts of ten woody non-host species of the pine weevil, Hylobius abietis.2008In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 34, no 10, p. 1290-1297Article in journal (Refereed)
  • 4.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Månsson, P
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Searching for Pine Weevil Antifeedants: Finding an Active Compound in Bark from Linden, Tilia cordata: Joint meeting of International Society of Chemical Ecology and Phytochemical Society of North America, Ottawa, Canada 20042004Conference paper (Other academic)
  • 5.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Schlyter, F
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Benzaldehyde, cinnamic aldehyde and related compounds as antifeedants against the pine weevil, Hylobius abietis: A study of structure-activity relationships.Manuscript (Other academic)
  • 6.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Schlyter, F
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Syntes av 2,6-disubstituerade piperidinalkaloider, potentiella gnaghämmare mot snytbaggen Hylobius abietis: 20:e Organikerdagarna, 12-15 juni 2006, Kalmar, föredrag2006Conference paper (Other academic)
  • 7.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Schlyter, Fredrik
    Swedish University of Agricultural Sciences, Alnarp.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Synthesis of (+)- and (-)-dihydropinidine by diastereoselective dimethylzinc promoted allylation of 2-methyltetrahydropyridine-N-oxide with allylboronic ester.2006In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, no 7, p. 1074-1080Article in journal (Refereed)
    Abstract [en]

    The enantiomers of the naturally occurring alkaloid dihydropinidine 1, potential antifeedants against the pine weevil, Hylobius abietis, were prepared by diastereoselective, dimethylzinc mediated addition of pinacolyl 2-propenylboronate 14 to nitrones (R)- and (S)-2-methyl tetrahydropyridine-N-oxide 3, prepared from d- and l-alanine, respectively.

  • 8.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Smitt, O.
    Schlyter, F.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Antifeedants for Protection of Pines and Spruces against the Pine Weevil, Hylobius abietis: International Society of Chemical Ecology, Annual Meeting 2001, Lake Tahoe, USA2001Conference paper (Other academic)
  • 9.
    Eriksson, Carina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Smitt, Olof
    Schlyter, Fredrik
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Searching for Pine Weevil Antifeedants, Strategy and Synthesis2002In: 19th annual meeting of International Society of Chemical Ecology, 2002, Hamburg, Germany, 2002, p. 217-Conference paper (Other academic)
  • 10.
    Fäldt, J.
    et al.
    Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Group of Ecological Chemistry, SE-100 44 Stockholm.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Persson, M.
    Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Group of Ecological Chemistry, SE-100 44 Stockholm.
    Valterová, I.
    Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
    Borg-Karlson, Anna-Karin
    Royal Institute of Technology, Department of Chemistry, Organic Chemistry, Group of Ecological Chemistry, SE-100 44 Stockholm.
    Correlations between selected monoterpene hydrocarbons in the xylem of six Pinus (pinaceae) species2001In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 11, no 2, p. 97-106Article in journal (Refereed)
    Abstract [en]

    The compositions of 23 monoterpene hydrocarbons of six pine species (Pinus sylvestris, P. yunnanensis ll,ris, P. armandii, P. tropicalis, P. cubensis and P. caribaca) were compared, using multivariate data analysis. Four of the six species were clearly different from the other species in a Principal Components Analysis (PCA) model, based on the relative amounts (selective normalization) of the monoterpenes. The correlation coefficients between constituents were determined separately for each species and the strongest correlations were found between (+)-alpha -pinene and (+)-camphene and between the corresponding (-)-enantiomers, in all species. This pattern, i.e. a good correlation in all species, was neither shown by the correlation of the structurally more similar (+)-alpha/beta -pinenes, nor by the (-)-alpha/beta -pinenes or within the enantiomeric pairs of alpha -pinene and beta -pinene. For these pairs of monoterpenes, good correlations were found in some species. None of the species showed good correlations in all the investigated monoterpene pairs presented here. Correlations between monoterpenes in insect-attacked trees (P. cubensis and P. caribaea, attacked by Dioryctria horneana, and P. yunnanensis, attacked by Tomicus piniperda) were also determined. The results are discussed from chemotaxonomic and biosynthetic points of view.

  • 11.
    Högberg, Hans-Erik
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Lindmark, Marica
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Isaksson, Dan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Franssen, M
    Jongejan, H
    Wijnberg, J
    de Groot, A
    Formation of hemiacetal esters in lipase-catalysed reactions of vinyl esters with hindered secondary alcohols2000In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 41, no 17, p. 3193-3196Article in journal (Refereed)
  • 12.
    Isaksson, Dan
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Enantioselektiv syntes av norterpenen Cryptone: 19:e Organikerdagarna, 14-17 juni, Linköping2004Conference paper (Other scientific)
  • 13.
    Isaksson, Dan
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Enantioselektiv syntes av seskviterpenen torreyol och andra kadinenderivat: 20:e Organikerdagarna, 12-15 juni 2006, Kalmar, Poster2006Conference paper (Other scientific)
  • 14.
    Isaksson, Dan
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Lindmark Henriksson, Marica
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hemiacetal ester formation in lipase catalysed transesterifications of vinyl esters with hindered secondary alcohols: Meeting abstract2003In: ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003Conference paper (Refereed)
  • 15.
    Isaksson, Dan
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Lindmark-Henriksson, Marica
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Hemiacetals and their esters as side-products in lipase catalysed transesterification of vinyl esters with sterically hindered alcohols2004In: Journal of Molecular Catalysis B: Enzymatic, ISSN 1381-1177, E-ISSN 1873-3158, Vol. 31, no 1-3, p. 31-37Article in journal (Refereed)
    Abstract [en]

    Hemiacetals and their esters are formed as side-products in lipase catalysed transesterification of vinyl esters with sterically hindered secondary alcohols. Scope and limitations of the reaction as well as the consequences of it for lipase catalysed kinetic resolutions are discussed.

  • 16.
    Isaksson, Dan
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Enantiomerically enriched cryptone by lipase catalysed kinetic resolution2006In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, no 2, p. 275-280Article in journal (Refereed)
    Abstract [en]

    Thiophenol was added to racemic cryptone (4-isopropyl-2-cyclohexene-1-one) and the resulting 1,4-addition products, cis- and trans-4-isopropyl-3-(phenylsulfanyl)cyclohexanone) were separated and the latter reduced to rac-1,3-cis-1,4-trans-4-isopropyl-3-(phenylsulfanyl)cyclo¬he¬xanol which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. The enantiomeric alcohols so obtained were oxidised. The initial products, probably sulfoxidoketones spontaneously decomposed to furnish enantiomerically enriched (R)- and (S)-cryptone with up to 76% and 98% ee, respectively.

  • 17.
    Lindmark Henriksson, Marica
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Isaksson, Dan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Vanek, Tomas
    Valterova, Irena
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Transformation of terpenes using a Picea abies suspension culture2004In: Journal of Biotechnology, ISSN 0168-1656, E-ISSN 1873-4863, Vol. 107, no 2, p. 173-184Article in journal (Refereed)
    Abstract [en]

    When subjected to a Picea abies suspension cell culture, beta-pinene, either one of the pure enantiomers or the racemate, was transformed mainly to trans-pinocarveol along with the minor products myrtenol, alpha-terpineol, pinocarvone, myrtenal and cis-pinocarveol. The absolute configuration of the major products corresponded to that of the starting beta-pinene enantiomer. Some of the primary transformation products, i.e. (1S)-cis- and (1S)-trans-pinocarveol, (1R)-myrtenol and (4S)-alpha-terpineol, were also tested as substrates of the P. abies suspension culture. They reacted more slowly than beta-pinene but, except for (4S)-alpha-terpineol, they were all transformed. Thus, (1R)-myrtenol was converted into both (1R)-myrtenal and (1R)-myrtanol, whereas (1S)-trans-pinocarveol was converted into (1S)-pinocarvone. (4R)-Limonene was slowly transformed by the suspension culture into limonene-(1,2)-epoxide as the major product, with carveol, perillyl alcohol and 1,8-cineole as minor products. Autoxidation of terpenes in cell-free nutrient medium was investigated in detail. alpha-Pinene and beta-pinene were both autoxidized to a certain extent, while limonene remained unaffected. The rate of the autoxidation was more than one order of magnitude slower than that of the biotransformation. Moreover, different products were formed by autoxidation than by biotransformation.

  • 18.
    Lindmark-Henriksson, Marica
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Isaksson, Dan
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Vanek, Tomas
    Valterova, Irena
    Transformation of alpha-pinene using Picea abies suspension culture2003In: Journal of Natural Products, ISSN 0163-3864, Vol. 66, no 3, p. 337-343Article in journal (Refereed)
    Abstract [en]

    alpha-Pinene, both as the pure enantiomers and as the racemate, was transformed mainly to trans-verbenol by treatment with a Picea abies suspension cell culture. These reactions were followed by a slow transformation of the verbenol to verbenone, which was not transformed further. trans-Pinocarveol, myrtenol, cis-verbenol, and alpha-terpineol were byproducts of intermediate abundance. When subjected to the action of the suspension culture, cis-verbenol was not only transformed to verbenone but also isomerized to trans-verbenol. The transformation of alpha-pinene was fast, and the products were detected within one minute. The absolute configuration of the major products corresponded to that of the starting alpha-pinene enantiomer

  • 19.
    Månsson, P. E.
    et al.
    Swedish University of Agricultural Sciences, Alnarp.
    Schlyter, F.
    Swedish University of Agricultural Sciences, Alnarp.
    Eriksson, Carina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Nonanoic acid, other alkanoic acids and related compounds as antifeedants in Hylobius abietis pine weevils2006In: Entomologia Experimentalis et Applicata, ISSN 0013-8703, E-ISSN 1570-7458, Vol. 121, no 3, p. 191-201Article in journal (Refereed)
    Abstract [en]

    A medium-length, straight-chain alkanoic acid, nonanoic acid, is known from laboratory microassays to be an antifeedant in adults of the large pine weevil, Hylobius abietis (L.) (Coleoptera: Curculionidae). Our hypothesis was that we could find new, less volatile alkanoic acids or related compounds suitable for field application and with improved long-term duration. Alkanoic acids of varying chain lengths (C6-C13) were tested for antifeedant activity in H. abietis adults. Microassay choice tests showed that straight-chain (C6-C11) alkanoic acids were active. However, high activities were restricted to the (C6-C10) acids, with the C9 (nonanoic acid) at 4 μmol cm-2 being the most active one. In a no-choice test on pine twigs, the antifeedant effect of C10 acid was lower than that of the C8 and C9 acids. In microassays, less volatile methyl-branched alkanoic acids exhibited lower antifeedant activities than did the corresponding straight-chain ones. However, the most active of the methyl-branched acids, 2-methyldecanoic acid, had an activity similar to that of nonanoic acid. Compounds related to nonanoic acid were either active (1-nonanol), weakly active (nonanoic anhydride), or inactive (nonanal, sodium nonanoate). The anhydride was highly active in the microassay, but less active on twigs. The antifeedant effects of the straight chain (C8-C10) alkanoic acids against pine weevil feeding were tested in the field. In contrast to the results from the twig tests, the less volatile C10 acid was more active in the field for the protection of transplants on fresh clear cuts over a 3-month period than both the C8 and C9 acids. Phytotoxic effects of the alkanoic acids were observed both in the field and in laboratory studies. If a protective layer of paraffin was applied to the stem prior to application of the alkanoic acids, these undesired side effects were reduced.

  • 20. Månsson, Per
    et al.
    Eriksson, Carina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Antifeedants against Hylobius abietis pine weevils: An active compound in extract of bark of Tilia cordata linden2005In: Journal of Chemical Ecology, ISSN 0098-0331, Vol. 31, no 5, p. 989-1001Article in journal (Refereed)
    Abstract [en]

    Linden (Tilia cordata) bark contains antifeedants effective against the large pine weevil, Hylobius abietis. Soxhlet extraction of inner and outer bark resulted in an extract which showed antifeedant activity in a micro-feeding assay. The extract was fractionated by chromatography on silica gel using gradient elution with solvents of increasing polarity. The content of the fractions obtained was monitored by thin layer- and gas chromatography. Fractions of similar chemical composition were merged. Two of the 17 fractions showed antifeedant activity in the micro feeding assay. Nonanoic acid was identified in both of these fractions. Subsequent testing in the micro feeding assay showed that nonanoic acid possessed strong antifeedant activity against H. abietis adults.

  • 21. Schlyter, F
    et al.
    Smitt, Olof
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Högberg, Hans-Erik
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Löfqvist, J
    Carvone and less volatile analogues as repellent and deterrent antifeedants against the pine weevil, Hylobius abietis2004In: Journal of applied entomology, ISSN 0931-2048, E-ISSN 1439-0418, Vol. 128, no 9-10, p. 610-619Article in journal (Refereed)
    Abstract [en]

    The monoterpenoid carvone (1) has been shown to have strong antifeedant effects on Hylobius spp. However, because of the high volatility of carvone, long-time protection of conifer seedlings in the field using this compound has not been possible. We demonstrate, in several bioassay steps, that less-volatile, heavier analogues retain their pre-ingestive feeding inhibition activity in the large pine weevil, Hylobius abietis (L.) for a longer time. The first step in the evaluation of the biological activity of 12 carvone analogues was a micro-assay, a choice test lasting 4 h. Compounds active at 100 nmol/cm(2) were further dose-response tested to give the effective dose needed to inhibit feeding by 50% (ED50). Of the 14 compounds tested, including both carvone enantiomers, seven heavier analogues were active at low doses (had low ED50 values). As expected from their lower vapour pressure compared with carvone, the heavier analogues proved more resistant to evaporation before testing. Thus, whereas the effect of 8-hydroxy-p-menth-en-6-one 4 declined after 2 days, some of the compounds with high molar masses, such as the alkylhydroxymenthenones 6 and 8, retained a stable activity for 4 days. The retained activity at 4 days was strongly correlated to molecular mass and boiling point. When tested on natural material (host Pinus sylvestris L. twig sections for 48 h), the heavier analogues showed a rather low activity. Probably, the activity of the more volatile compound carvone (1) is due to a repellent effect (olfactory mode) rather than the deterrent effects (gustatory mode) of the heavier compounds. In agreement with the relatively low activity on twigs in the laboratory, the hydroxymenthenone 4 was not active in the field when tested for 2 months as a 1 : 9 mixture with a polar wax.

  • 22. Shtykova, Liubov
    et al.
    Masuda, Mariam
    Eriksson, Carina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Sjödin, Kristina
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
    Marling, Elisabeth
    Schlyter, Fredrik
    Nydén, Magnus
    Latex coatings containing antifeedants: formulation, characterization, and application for protection of conifer seedlings against pine weevil feeding.2008In: Progress in organic coatings, ISSN 0300-9440, E-ISSN 1873-331X, Vol. 63, no 2, p. 160-166Article, review/survey (Refereed)
    Abstract [en]

    Latex-based coatings for protection of tree seedlings against pest insect feeding are evaluated with respect to surface-, mechanical-, and release properties and antifeedant activity. The latex dispersion Eudragit copolymer (EC) was used to form the coatings, 2,6-di-tert-butyl-4-methylphenol (BHT) and cis-dihydropinidine (Alk) as antifeedants, and a thickener and a alkylglucoside based nonionic surfactant were used as additives to optimize the release- and mechanical properties of coatings. Coating characterization was performed with respect to surface morphology (atomic force microscopy, AFM) and surface wetting (contact angle), as well as to mechanical (tensile stress- and tensile strain at break) properties. Surface smoothness and wettability as well as elasticity increased with addition of the surfactant. The optimized coatings were found to be elastic and water resistant at 3-6 wt.% of BHT and 3 wt.% of surfactant. BHT was released into SDS/water at very low rates. Several formulations of BHT and Alk were efficient in preventing the feeding on conifer bark by a pine insect, Hylobius abietis both in laboratory (no-choice) and in held Q months) tests.

  • 23.
    Sjödin, Kristina
    et al.
    Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
    Persson, M.
    Faldt, J.
    Ekberg, I.
    Borg-Karlson, A. K.
    Occurrence and correlations of monoterpene hydrocarbon enantiomers in Pinus sylvestris and Picea abies2000In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 26, no 7, p. 1701-1720Article in journal (Refereed)
    Abstract [en]

    The relative amounts and enantiomeric compositions of monoterpene hydrocarbons in branch and trunk xylem, in needles, and in resin from apical buds in 18 Pinus sylvestris trees have been determined and compared with the terpene content in branch xylem and needles of Picea abies. Besides the high amount of (+)-3-carene, an excess of (+)-alpha-pinene has been found in P. sylvestris, whereas in P. abies (-)-alpha-pinene dominates over (+)-alpha-pinene. In P. sylvestris, clear positive correlations were found between (+)-alpha-pinene and (+)-camphene in the four tissues analyzed. Good positive correlations were also observed between (-)-alpha-pinene and (-)-camphene in the two types of xylem, between (+)-alpha-pinene and (+)-beta-pinene in the resin, and between tricyclene and (-)-camphene in resin and needles. In P. abies, positive correlations were found between (+)-alpha-pinene and (+)-camphene in the branch xylem and between tricyclene and (-)-camphene as well as between (-)-alpha-pinene and (-)-camphene in the needles. Complex relationships between (-)-alpha-pinene and (-)-beta-pinene were found both in the P. abies and in the P. sylvestris tissues. The importance of the enantiomeric composition of alpha-pinene for the host selection of Ips typographus, Tomicus piniperda, and Hylobius abietis is discussed.

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