- About this Journal
- Abstracting and Indexing
- Aims and Scope
- Annual Issues
- Article Processing Charges
- Articles in Press
- Author Guidelines
- Bibliographic Information
- Citations to this Journal
- Contact Information
- Editorial Board
- Editorial Workflow
- Free eTOC Alerts
- Publication Ethics
- Reviewers Acknowledgment
- Society Affiliation
- Submit a Manuscript
- Subscription Information
- Table of Contents
Volume 2012 (2012), Article ID 414508, 7 pages
2-methyl-3-buten-2-ol: A Pheromone Component of Conifer Bark Beetles Found in the Bark of Nonhost Deciduous Trees
1Chemical Ecology, Department of Plant Protection Biology, Swedish University of Agricultural Sciences, P.O. Box 102, 230 53 Alnarp, Sweden
2R&D Department, Sterling International, Inc., 3808 N. Sullivan Road Building 16, Spokane, WA 99216, USA
Received 30 December 2011; Accepted 9 February 2012
Academic Editor: John A. Byers
Copyright © 2012 Qing-He Zhang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- Q. H. E. Zhang, G. Birgersson, J. Zhu, C. Löfstedt, J. Löfqvist, and F. Schlyter, “Leaf volatiles from nonhost deciduous trees: variation by tree species, season and temperature, and electrophysiological activity in Ips typographus,” Journal of Chemical Ecology, vol. 25, no. 8, pp. 1923–1943, 1999.
- J. A. Byers, Q. H. Zhang, F. Schlyter, and G. Birgersson, “Volatiles from nonhost birch trees inhibit pheromone response in spruce bark beetles,” Naturwissenschaften, vol. 85, no. 11, pp. 557–561, 1998.
- Q. H. Zhang and F. Schlyter, “Olfactory recognition and behavioural avoidance of angiosperm nonhost volatiles by conifer-inhabiting bark beetles,” Agricultural and Forest Entomology, vol. 6, no. 1, pp. 1–19, 2004.
- Q. H. Zhang, F. Schlyter, and P. Anderson, “Green leaf volatiles interrupt pheromone response of spruce bark beetle, Ips typographus,” Journal of Chemical Ecology, vol. 25, no. 12, pp. 2847–2861, 1999.
- Q. H. Zhang, F. Schlyter, and G. Birgersson, “Bark volatiles from nonhost angiosperm trees of spruce bark beetle, Ips typographus (L.) (Coleoptera: Scolytidae): chemical and electrophysiological analysis,” Chemoecology, vol. 10, no. 2, pp. 69–80, 2000.
- G. Birgersson, F. Schlyter, J. Löfqvist, and G. Bergström, “Quantitative variation of pheromone components in the spruce bark beetle Ips typographus from different attack phases,” Journal of Chemical Ecology, vol. 10, no. 7, pp. 1029–1055, 1984.
- G. Birgersson and G. Bergström, “Volatiles released from individual spruce bark beetle entrance holes quantitative variations during the first week of attack,” Journal of Chemical Ecology, vol. 15, no. 10, pp. 2465–2483, 1989.
- A. Bakke, P. Froyen, and L. Skattebol, “Field response to a new pheromonal compound isolated from Ips typographus,” Naturwissenschaften, vol. 64, no. 2, pp. 98–99, 1977.
- B. S. Lanne, P. Ivarsson, P. Johnsson, G. Bergström, and A. B. Wassgren, “Biosynthesis of 2-methyl-3-buten-2-ol, a pheromone component of Ips typographus (Coleoptera: Scolytidae),” Insect Biochemistry, vol. 19, no. 2, pp. 163–167, 1989.
- T. Zhao, A.-K. Borg-Karlson, N. Erbilgin, and P. Krokene, “Host resistance elicited by methyl jasmonate reduces emission of aggregation pheromones by the spruce bark beetle, Ips typographus,” Oecologia, vol. 167, no. 3, pp. 691–699, 2011.
- H. Giesen, U. Kohnle, J. P. Vité, M.-L. Pan, and W. Francke, “Das Aggregationspheromon des mediterranen Kiefernborkenkäfers Ips (Orthotomicus) erosus,” Journal of Applied Entomology, vol. 98, no. 1, pp. 95–97, 1984.
- Q. H. Zhang, J. H. Ma, F. Y. Zhao, L. W. Song, and J. H. Sun, “Aggregation pheromone of the qinghai spruce bark beetle, Ips nitidus eggers,” Journal of Chemical Ecology, vol. 35, no. 5, pp. 610–617, 2009.
- Q. H. Zhang, L. W. Song, J. H. Ma, F. Z. Han, and J. H. Sun, “Aggregation pheromone of a newly described spruce bark beetle, Ips shangrila Cognato and Sun, from China,” Chemoecology, vol. 19, no. 4, pp. 203–210, 2009.
- D. Klimetzek, J. Bartels, and W. Francke, “Das Pheromon-System des Bunten Ulmenbastkäfers Pteleobius vittatus (F.) (Col., Scolytidae),” Journal of Applied Entomology, vol. 107, no. 5, pp. 518–523, 1989.
- E. J. Baader, “Pityogenes spp. (Col., Scolytidae): investigations on semiochemicals and their application in forest protection,” Journal of Applied Entomology, vol. 107, no. 1, pp. 1–31, 1989.
- M. Zuber, “Racemate and enantiomers of ipsdienol for attracting Ips amitinus (Eichh.) (Col., Scolytidae),” Anzeiger für Schaedlingskunde Pfanzenschutz Unweltschutz, vol. 67, no. 5, pp. 92–93, 1994.
- H. J. Veith, N. Koeniger, and U. Maschwitz, “2-methyl-3-butene-2-ol, a major component of the alarm pheromone of the hornet Vespa crabro,” Naturwissenschaften, vol. 71, no. 6, pp. 328–329, 1984.
- R. Kaiser, The Scent of Orchids, Elsevier, Amsterdam, The Netherlands, 1993.
- R. Wohlfart, R. Hansel, and H. Schmidt, “Sedative hypnotic principles in hops. Part 4. Pharmacology of the hop constituent 2-methyl-3-buten-2-ol,” Planta Medica, vol. 48, no. 2, pp. 120–123, 1983.
- R. Wohlfart, G. Wurm, R. Hansel, and H. Schmidt, “edative hypnotic principles in hops. Part 5. degradation of humulones and lupulones to 2-methyl-3-buten-2-ol, a hop constituent possessing sedative hypnotic activity,” Archiv der Pharmazie, vol. 316, no. 2, pp. 132–137, 1983.
- G. J. Mannering and J. A. Shoeman, “Murine cytochrome P4503A is induced by 2-methyl-3-buten-2-ol, 3-methyl-1-pentyn-3-ol(meparfynol), and tert-amyl alcohol,” Xenobiotica, vol. 26, no. 5, pp. 487–493, 1996.
- M. Dicke, “Behavioural and community ecology of plants that cry for help,” Plant, Cell and Environment, vol. 32, no. 6, pp. 654–665, 2009.
- D. McGinty, J. Scognamiglio, C. S. Letizia, and A. M. Api, “Fragrance material review on 2-methyl-3-buten-2-ol,” Food and Chemical Toxicology, vol. 48, supplement 3, pp. S97–S100, 2010.
- P. Zimmerman, W. Pollack, A. Guenther, and H. Westberg, “Field deployment of a GC-MS system for determination of biogenic hydrocarbons in vegetation enclosures and ambient air (abstract),” Eos Transactions, American Geophysical Union, vol. 72, p. 88, 1991.
- P. D. Goldan, W. C. Kuster, F. C. Fehsenfield, and S. A. Montzka, “The observation of a C5 alcohol emission in a north American pine forest,” Geophysical Research Letters, vol. 20, no. 11, pp. 1039–1042, 1993.
- P. Harley, V. Fridd-Stroud, J. Greenberg, A. Guenther, and P. Vasconcellos, “Emission of 2-methyl-3-buten-2-ol by pines: A potentially large natural source of reactive carbon to the atmosphere,” Journal of Geophysical Research D, vol. 103, no. 19, pp. 25479–25486, 1998.
- A. M. El-Sayed, V. J. Heppelthwaite, L. M. Manning, A. R. Gibb, and D. M. Suckling, “Volatile constituents of fermented sugar baits and their attraction to Lepidopteran species,” Journal of Agricultural and Food Chemistry, vol. 53, no. 4, pp. 953–958, 2005.
- J. Stökl, A. Strutz, A. Dafni et al., “A deceptive pollination system targeting drosophilids through olfactory mimicry of yeast,” Current Biology, vol. 20, no. 20, pp. 1846–1852, 2010.
- G. Fantechi, N. R. Jensen, J. Hjorth, and J. Peeters, “Mechanistic study of the atmospheric degradation of isoprene and MBO,” in Proceedings of the EUROTRAC symposium, pp. 397–340, Computational Mechanics, 1996.
- C. Ferronato, J. J. Orlando, and G. S. Tyndall, “Rate and mechanism of the reactions of OH and Cl with 2-methyl-3-buten-2-ol,” Journal of Geophysical Research D, vol. 103, no. 19, pp. 25579–25586, 1998.
- D. Grosjean and E. Grosjean, “Carbonyl products of the ozone-unsaturated alcohol reaction,” Journal of Geophysical Research, vol. 100, no. 11, pp. 22815–22820, 1995.
- E. Grosjean and D. Grosjean, “Rate constants for the gas-phase reactions of ozone with unsaturated aliphatic alcohols,” International Journal of Chemical Kinetics, vol. 26, no. 12, pp. 1185–1191, 1994.
- M. Hallquist, S. Langer, E. Ljungström, and I. Wängberg, “Rates of reaction between the nitrate radical and some unsaturated alcohols,” International Journal of Chemical Kinetics, vol. 28, no. 6, pp. 467–474, 1996.
- Y. Rudich, R. Talukdar, J. B. Burkholder, and A. R. Ravishankara, “Reaction of methylbutenol with hydroxyl radical: mechanism and atmospheric implications,” Journal of Physical Chemistry, vol. 99, no. 32, pp. 12188–12194, 1995.
- A. W. H. Chan, M. M. Galloway, A. J. Kwan et al., “Photooxidation of 2-methyl-3-buten-2-ol (MBO) as a potential source of secondary organic aerosol,” Environmental Science and Technology, vol. 43, no. 13, pp. 4647–4652, 2009.
- T. M. Fu, D. J. Jacob, F. Wittrock, J. P. Burrows, M. Vrekoussis, and D. K. Henze, “Global budgets of atmospheric glyoxal and methylglyoxal, and implications for formation of secondary organic aerosols,” Journal of Geophysical Research D, vol. 113, no. 15, Article ID D15303, 17 pages, 2008.
- A. Guenther, T. Karl, P. Harley, C. Wiedinmyer, P. I. Palmer, and C. Geron, “Estimates of global terrestrial isoprene emissions using MEGAN (Model of Emissions of Gases and Aerosols from Nature),” Atmospheric Chemistry and Physics, vol. 6, no. 11, pp. 3181–3210, 2006.
- J. C. Dickens, “Behavioral and electrophysiological responses of the bark beetle, Ips typographus, to potential pheromone components,” Physiological Entomology, vol. 6, no. 3, pp. 251–261, 1981.
- F. Schlyter, J. Lofqvist, and J. A. Byers, “Behavioural sequence in the attraction of the bark beetle Ips typographus to pheromone sources,” Physiological Entomology, vol. 12, no. 2, pp. 185–196, 1987.
- R. A. Werner and E. H. Holsten, “Current status of research with the spruce beetle Dendroctonus rufipennis,” in Application of Semiochemicals for Management of Bark Beetle Infestations—Proceedings of an Informal Conference USDA For Ser Gen Tech Rep INT-GTR-318, S. M. Salom and K. R. Hobson, Eds., pp. 23–29, 1995.
- D. W. Gray, “Field response of Ips paraconfusus, Dendroctonus brevicomis, and their predators to 2-methyl-3-buten-2-ol, a novel alcohol emitted by ponderosa pine,” Journal of Chemical Ecology, vol. 28, no. 8, pp. 1583–1597, 2002.
- D. W. Gray, S. R. Breneman, L. A. Topper, and T. D. Sharkey, “Biochemical characterization and homology modeling of methylbutenol synthase and implications for understanding hemiterpene synthase evolution in plants,” The Journal of Biological Chemistry, vol. 286, no. 23, pp. 20582–20590, 2011.
- A. J. Fisher, B. M. Baker, J. P. Greenberg, and R. Fall, “Enzymatic synthesis of methylbutenol from dimethylallyl diphosphate in needles of Pinus sabiniana,” Archives of Biochemistry and Biophysics, vol. 383, no. 1, pp. 128–134, 2000.