PHEROMONES OF PINE SAWFLIES.
STRUCTURES, SYNTHESES AND APPLICATIONS

Hans-Erik Högberg, Erik Hedenström
Department of Chemistry and Process Technology, Mid Sweden University, S-851 70 Sundsvall, SWEDEN. E-mail: Hans-Erik.Hogberg@kep.mh.se

The diprionid sawflies cause serious pests in European pine forests. Thus larvae from especially Neodiprion sertifer, Diprion pint, Gilpinia frutelorum, Microdiprion pallipes and Macrodiprion nemoralis are responsible for the defoliation of large areas.

We are presently engaged in a EU-project (PHERODIP) with the goal to develop pheromone based control methods for the diprionid sawflies including monitoring and mass disruption.

The pheromones from diprionid sawflies, identified so far, are long chain secondary esters carrying a varying number of methyl groups. Consequently, these pheromones are chiral compounds. In most species only one stereoisomer is the attractant, while others may have inhibitory effects.-1 Thus, when a synthetic pheromone preparation is used for catching Neodipffon sender, the stereoisomeric purity of the sample is extremely important for the biological activity.

We have developed highly selective synthetic routes to allow for the preparation of enantiomerically and diastereomerically pure sawfly pheromones.-2-4

1. O. Anderbrant, J. Löfqvist, E. Hedenström, H.-E. Högberg, M. Bengtsson, G. Magnusson, Entomologia Experimentalis et Applicata, 62, 169-181 (1992)
2. H.-E. Högberg, E. Hedenström, A.-B. Wassgren, M. Hjalmarsson, G. Bergström, J. Löfqvist, T. Norin, Tetrahedron, 46, 3007-3018 (1990).
3. E. Hedenström, H.-E. Högberg, Tetrahedron, 50, (1994) 5225-5232.
4. H.-E Högberg, P. Berglund, H. Edlund, J. Fägerhag, E. Hedenström, M. Lundh, O. Nordin, S. Servi, C. Vörde, Catalysis Today 22, (1995) 591-606.
5. G. Bergström, A.-B. Wassgren, O. Anderbrant, E. Hedenstrom J. Fägerhag, H. Edlund, C. Geri, M. Varama, B. S. Hansson, J. Löfqvist, H.-E Högberg, Experientia, 51, (1995) 370-380.