Levoverbenone

Levoverbenone

Levoverbenone
Systematic (IUPAC) name
(1S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
Clinical data
Legal status
?
Identifiers
CAS number  Y
ATC code R05
PubChem
ChemSpider  Y
UNII  Y
ChEBI  N
Chemical data
Formula C10H14O 
Mol. mass 150.218 g/mol
 N   

Levoverbenone is an expectorant. It is the L-isomer of verbenone.

Use of Levoverbenone for insect control

The southern pine beetle (Dendroctonus frontalis), a bark beetle, is a major threat to pine trees in the southeastern United States. Its reproductive cycle is controlled by varying ratios of certain natural chemicals, including verbenone. To reproduce, pine bark beetles aggregate in large numbers in their host pine trees. At the beginning of an attack, various chemicals produced by infested trees and by the beetles attract additional beetles of the same species. When the numbers of adults and larvae approach the maximum that the tree can support, antiaggregation signal chemicals, i.e., verbenone, are produced, reducing the likelihood that additional beetles will land and attack the tree. Forest managers frequently try to control infestations of the Southern pine bark beetle by cutting down and sometimes burning infested trees and nearby healthy trees. They then place verbenone formulations on nearby susceptible healthy trees to repel and confuse the beetles.[1]

Levoverbenone or (-)Verbenone is also used to manage mountain pine beetle (Dendroctonus ponderosae) infestations.[2] Verbenone is the principal antiaggregation pheromone of the mountain pine beetle, Dendroctonus ponderosae Hopkins, a notable forest insect capable of causing extensive levels of tree mortality in western North America. Although several formulations of verbenone have been registered with the U.S. Environmental Protection Agency [3] for tree protection, failures in efficacy are rather common. Unlike previous formulations, a new formulation of (–)-verbenone registered as SPLAT® Verb [4] (ISCA Technologies Inc., Riverside, CA) was found to be extremely efficient in protecting individual lodgepole pine, Pinus contorta Dougl. ex Loud., and small stands of P. contorta from mortality attributed to D. ponderosae. SPLAT® Verb applications resulted in complete individual P. contorta tree protection while 93.3% mortality occurred in the untreated controls; furthermore significantly fewer P. contorta were killed by D. ponderosae within 0.041-ha circular plots (11-m radius) surrounding P. contorta treated with SPLAT® Verb compared to the untreated control.[5]

References

  1. ^ U.S. Environmental Protection Agency Pesticide Fact Sheet #128986.
  2. ^ Mafra-Neto, Agenor; de Lame, Frédérique M.; Fettig, Christopher J.; Perring, Thomas M.; Stelinski, Lukasz L.; Stoltman, Lyndsie L.; Mafra, Leandro E. J.; Borges, Rafael; Vargas, Roger I. (2013). "Manipulation of Insect Behavior with Specialized Pheromone and Lure Application Technology (SPLAT®)". In John Beck, Joel Coats, Stephen Duke, and Marja Koivunen. Natural Products for Pest Management 1141. American Chemical Society. pp. 31–58. 
  3. ^ U.S. Environmental Protection Agency Pesticide Fact Sheet #128986.
  4. ^ SPLAT Verb Information Page http://www.iscatech.com/exec/SPLATVerbtest.html
  5. ^ Mafra-Neto, Agenor; Fettig, Christopher J.; Munson, A.S.; Stelinski, Lukasz L. (2014). "The use of repellents formulated in Specialized Pheromone and Lure Application Technology (SPLAT®) for effective insect pest management.". In Debboun, M., S.P. Francis, and D.A. Strickman. Insect Repellents Handbook, Second Edition. Taylor & Francis, London. pp. 291–314.