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

Naturwissenschaften

Volumn 87, Issue 1, 2000, Pages 24-29

  Wassgren, A B ^a   Bergstrom G ^a   Sierpinski, A ^d   Anderbrant, O ^b   Hogberg H E ^c   Hedenstrom E ^c  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b LUND UNIVERSITY   (Sweden)

^c MID SWEDEN UNIVERSITY   (Sweden)

^d FOREST RESEARCH INSTITUTE   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

3,7,9 TRIMETHYL 2 TRIDECANOL; HORMONE PRECURSOR; PHEROMONE; THREO 3,7,9 TRIMETHYL 2 TRIDECANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; FLY; GAS CHROMATOGRAPHY; HORMONE DETERMINATION; MASS SPECTROMETRY; NONHUMAN; SPECIES DIFFERENCE; STEREOISOMERISM;

ALCOHOLS; ANIMALS; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYMENOPTERA; PHEROMONES;

EID: 0033957202     PISSN: 00281042     EISSN: None     Source Type: Journal    
DOI: 10.1007/s001140050003     Document Type: Article

References (14)

1. Anderbrant O (1993) Pheromone biology of sawflies. In: Wagner MR, Raffa KF (eds) Sawfly life history adaptations to woody plants. Academic, San Diego, pp 119-154
2. Anderbrant O, Löfqvist J, Jönsson J, Marling E (1989) Effect of pheromone trap type, position, and colour on the catch of the pine sawfly Neodiprion sertifer (Geoffr.) (Hym. Diprionidae). J Appl Entomol 107:365-369
3. Anderbrant O, Hansson BS, Hallberg E, Geri C, Varama M, Hedenström E, Högberg H-E, Fägerhag J, Edlund H, Wassgren A-B, Bergström G, Löfqvist J (1995) Electrophysiological and morphological characteristics of pheromone receptors in male pine sawflies, Diprion pini (Hymenoptera: Diprionidae), and behavioural response to some compounds. J Insect Physiol 41:395-401
4. Bergström G, Wassgren A-B, Anderbrant O, Fägerhag J, Edlund H, Hedenström E, Högberg H-E, Geri C, Auger MA, Varama M, Hansson BS, Löfqvist J (1995) Sex pheromone of the pine sawfly Diprion pini (Hymenoptera: Diprionidae): chemical identification, synthesis and biological activity. Experientia 51:370-380
5. Bergström G, Wassgren A-B, Anderbrant O, Ochieng SA, Östrand F, Hansson BS, Hedenström E, Högberg H-E (1998) The sex pheromone of the pine sawfly Microdiprion pallipes (Hymenoptera: Diprionidae). Naturwissenschaften 85:244-248
6. Högberg H-E, Hedenström E, Wassgren A-B, Hjalmarsson M, Bergström G, Löfqvist J, Norin T (1990) Synthesis and gas chromatographic separation of the eight stereoisomers of diprionol and their acetates, components of the sex pheromone of pine sawflies. Tetrahedron 46:3007-3018
7. Jewett D, Matsumura F, Coppel HC (1976) Sex pheromone specificity in the pine sawflies: interchange of acid moieties in an ester. Science 192:51-53
8. Karlsson S, Hedenström E (1999) Sex Pheromone of the Pine Sawfly Macrodiprion nemoralis. Stereoselective syntheses of all the sixteen stereoisomers of 3, 7, 9-dimethyl-2-tridecyl acetate. Acta Chem Scand 53:620-630
9. König WA, Francke W, Benecke I (1982) Gas chromatographic enantiomer separation of chiral alcohols. J Chromatogr 239:227-231
10. Pschorn-Walcher H (1982) Unterordnung Symphyta, Pflanzenwespen. In: Schwenke W (ed) Die Fortschädlinge Europas. Parey, Hamburg, pp 4-234
11. Smith DR (1993) Systematic, life history and distribution of sawflies. In: Wagner MR, Raffa KF (eds) Sawfly life history adaptations to woody plants. Academic, San Diego, pp 3-32
12. Sturm H (1942) Untersuchungen über Buschhornblattwespen (Diprion). Z Angew Entomol 29:601-635
13. Tai A, Higashiura Y, Kakizaki M, Naito T, Tanaka K, Fujita M, Sugimura T, Hara H, Hayashi N (1998) Field and electroantennogram responses of the pine sawfly, Diprion nipponica, to chiral synthetic pheromone candidates. Biosci Biotechnol Biochem 62:607-608
14. Wassgren A-B, Anderbrant, O, Löfqvist J, Hansson BS, Bergström G, Hedenström E, Högberg H-E (1992) Pheromone related compound in pupal and adult female pine sawflies, Neodiprion sertifer, of different age and in different parts of the body. J Insect Physiol 38:885-893