(E8,Z10)-TETRADECA-8,10-DIENAL,VERFAHREN ZU SEINER HERSTELLUNG UND SEINE VERWENDUNG ALS SEXUALLOCKSTOFF FÜR MINIERMOTTEN

摘要

The subject of the invention are isomerically pure tetradeca-8,10-dienals, the synthetic preparation thereof and their use as sex attractants for leafminers of the genus Gracillariidae (Lepidotpera, Insecta), in particular the means of preparation of the (E8,Z10)-tetradeca-8,10-dienal and its utilization as a sex attractant for horse chestnut leafminer [Cameraria ohridella Deschka et Dimić1985 (Lepidoptera:Gracillariidae)]. The title compound can be prepared so that (E)-9-(tert-butoxy)-1-jodnon-1-ene reacts with 1-pentyne in a basic solvent, preferably an alkylamine, in the presence of a Pd(0) catalyst mixed with a cuprous salt providing (E))-14-(tert-butoxy)tetradec-6-en-4-yne, whereupon the above prepared enyne is reduced to provide (4Z,6E)-14-(tert-butoxy)tetradeca-4,6-diene, then a protection group is removed in an acidic environment and the prepared (8E,10Z)-tetradeca-8,10-dien-1-ol is further oxidized to give the (E8,Z10)-tetradeca-8,10-dienal. This compound is directly, in a solution or in a mixture with additional compounds, or in the form of its pro-pheromone derivatives, applied on an appropriate support and then used in diverse types of traps containing, beside the attractant, a moth restraint to control populations of the horse chestnut leafminer, or in mass-trapping devices for the moth males or in devices containing, beside the attractant, insecticides, a biocontrol agent, or compounds regulating insect development (IGR-Insect Growth Regulators), in which the attracted males are killed, or agents spread into leafminer populations, or, finally, the title compound can be dispersed into the atmosphere in concentrations capable of confusing the males and thus preventing their copulation with conspecific females.