Douglas fir beetle

The stoichiometric approach has been successfully used as the key step for the synthesis of biologically active compounds, to obtain enantioenriched allylic alcohols, as illustrated by the synthesis of conduritols derivatives 84 or the aggregation pheromone of the Douglas-fir beetle 85 , as well as enantioenriched oxiranes, intermediates for the synthesis of (—)-isomenthone 86 ° (Scheme 34). 

Huber D. W. P. and Borden J. H. (2001) Angiosperm bark volatiles disrupt response of Douglas-fir beetle, Dendroctonus pseudotsugae, to attractant-baited traps. J. Chem. Ecol. 27, 217-233. 

Libbey L. M., Morgan M. E., Putnam T. B. and Rudinsky J. A. (1976) Isomer of antiaggregation pheromone identified from male Douglas-fir beetle 3-methylcyclohex-3-en-l-one. J. Insect Physiol. 22, 871-873. 

Lindgren B. S. (1992) Attraction of Douglas-fir beetle, spruce beetle and a bark beetle predator (Coleoptera Scolytidae and Cleridae) to enantiomers of frontalin. J. Entomol. Soc. Brit. Columbia 89, 13-17. 

Pitman G. B. and Vite J. P. (1974) Biosynthesis of methylcyclohexenone by male Douglas-fir beetle. Environ. Entomol. 3, 886-887. 

Rudinsky J. A., Kinzer G. W., Fentiman A. F., Jr, and Foltz, R. L. (1972) fraws-Verbenol isolated from Douglas-fir beetle laboratory and field bioassay in Oregon. Environ. Entomol. 1, 485-488. 

Ryker L. C., Libbey L. M. and Rudinsky J. A. (1979) Comparison of volatile compounds and stridulation emitted by the Douglas-fir beetle from Idaho and western Oregon populations. Environ. Entomol. 8, 789-798. 

Most of the new synthetic work on cyclobutane monoterpenoids concerns the insect pheromone (+ )-grandisol (295) (Vol. 2, p. 58 Vol. 4, p. 488) and (+ )-lineatin (296), a pheromone of the Douglas fir beetle, Trypodendron lineatum (Vol. 4, p. 489, Ref. 255). There are, however, two other syntheses described, and these will be dealt with first. 

Frontalin (98, Figure 4.49) is the active component of the aggregation pheromone of the southern pine beetle (Dendroctonus frontalis), the western pine beetle (Dendroctonus brevicomis) and the Douglas-fir beetle (Dendroctonuspseudotsugae). Mori s 1975 synthesis of the enantiomers of frontalin via enantiomer separation (optical resolution) of an intermediate87 enabled their bioassay, and only (lS,5/ )-98 was bioactive as the pheromone component of D. brevicomis.32 A recent study on female D. frontalis revealed its (15, 5/C)-98 to be of about 91% ee.88... 

Females of the Douglas-fir beetle (Dendroctonuspseudotsugae) produce an average of a 55 45 mixture of (R)- and (5 )-119. The combined effect of the enantiomers was additive rather than synergistic, and both enantiomers are required for maximum response.140... 

Cyclobutane.—A tricyclic acetal named lineatin has been isolated from the frass of the Douglas fir beetle Trypodendron lineatum structural elucidation and synthesis have not distinguished between (104) and (105). ... 

C7H1A Mr 112.17, liquid, bp. 83-84°C (2.73 kPa) ( )-enantiomer [a] +96° (CHCI3). Aggregation pheromone of the American bark beetle Dendroctonus pseudotsugae (Douglas fir beetle). The natural product exists as an enantiomeric mixture containing 55-65% (+)-(/f)-S. 

Rudinsky, J. A., Morgan, M. Libbey, L. M. and Michael, R. R. (1973) Sound production in Scolytidae 3-Methyl-2-cyclohexen-l-one released by the female Douglas fir beetle in response to male sonic signal. Env, Ent, 2, 505-9. 

In Dendroctonus species, stridulation may trigger the release of pheromones that deter further arrivals. Thus arriving male D. pseudotsugae (Douglas fir beetle) stridulate outside the females entrance hole, stimulating her to release... 

Component of the aggregation pheromone of the douglas fir beetle Dendroctonus psuedotsugae. 

The Douglas-fir beetle has also been attracted with pheromones to bait trees that were scheduled for logging 548). No attempt at economic assessment was made, but the method is certainly limited to areas that are readily accessible and are scheduled for prompt logging. 

L. F. Pettinger, and J. A. Rudinsky Effectiveness of the Douglas-fir beetle anti-aggregative pheromones methylcyclohexanone at three concentrations and spacings around felled host trees. Can. Entomol. 108, 381—392 (1974). 

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