Novel Synthetic Strategy and Field Testing Tomato Pinworm Pheromone in Armenia.

Abstract

Two synthon C10 + C3 strategy syntheses of tomato pinworm sex pheromone- (E)-, (Z)-tridec-4-en-1-yl acetates- were illustrated. The iodinated dec-1-yn was successfully applied as a substrate in the synthesis of sex pheromone. The C10-component-1-iododec-1-yne was first obtained by the electrophilic iodination of dec-1-yne in the presence of cadmium (II) acetate. Additionally, the C3 component was produced from 2-(3-bromopropoxy) tetrahydro-2H-pyran by the Grignard reaction. The most important stage was the coupling of C10 and C3 components, and condensation in tetrahydrofuran in the presence of dilithium tetrachlorocuprate was carried out due to the great reactivity of the 1-iododec-1-yne. The dispensers were made based on the target sex pheromone and located in the traps. The active preparative forms were tested in field conditions in some regions of Armenia in 2024. Based on the field studies Keiferia lycopersicella belonging to the family Gelechiidae was recorded in Armenia (Armavir, Ararat, Tavush, and Kotayk regions) for the first time.