Hydrocarbon components of the yellowheaded spruce sawfly sex pheromone : A series of (Z, Z)-9, 19 dienes

Abstract

The primary sex pheromone of the yellowheaded spruce sawfly,Pikonema alaskensis (Rohwer) (Hymenoptera: Tenthredinidae), was found to include a series of straight-chain hydrocarbon dienes, all with the double bonds in the 9 and 19 positions and all with the (Z, Z) configuration. The major components, of 29, 31, 33, 35, and 37 carbon atoms, were synthesized. In the field and the greenhouse, the synthetic dienes were far above control levels in activity but, at least during the first hours of bioassay, were somewhat less active than the female-derived materials on a weight basis. In the field, a mixture of all five synthetic dienes, in the proportions found in the females, was more attractive than any single one, on a mole basis. In addition, (Z, Z)-9,19 dienes of 28, 30, 32, 34, 36, 38, and 39 carbons have been detected in females in minor amounts. The first five were bioassayed, and each was found to be similar in activity to the 35-carbon component when compared on a weight basis. The synthetic dienes, while active by themselves, were strongly synergized by two, more polar, Florisil fractions derived from females. Experimental design considerations are discussed.