Pheromone synthesis. XXI. Synthesis of (Z,Z)-3,13-octadecadienyl acetate and its (E,Z)-isomer, the attractant for the cherrytree borer.

By screening singly and binary mixed 2,13- and 3,13-octadecadien-yl acetates and alcohols (2,13- and 3,13-18: Ac/OH)in Lithuania, Armenia, Azerbaijan, Turkmenistan, Ukraine, and the far east of Russia, sex attractants were discovered for 12 Sesiidae, four Tineidae, and one Choreutidae moth species. Males ofSesia yezoensis andBembecia puella as well asNemapogon flavifrons were attracted by mixture ofZ3,Z13-18:Ac/OH in a ratio of 9∶1,Pyropteron sp. n. by the same mixture (ratio 1∶9),Bembecia romanovi andB. zuwandica byZ3,Z13-18:Ac andE3,Z13-18:Ac (9∶1),Synanthedon caucasicum by the same mixture in the opposite ratio (1∶9),B. scopigera by 23,213-18:Ac andE2,Z13-18:OH in a ratio 9∶1,Synasphecia triannuliformis byZ3,Z13-18:OH andE3,Z13-18:OH (9∶1),Similipepsis takizawai andArchimeessia sp. n. by E3,Z13-18:OH andE2,Z13-18:Ac (1∶1),Prochoreutis sechestediana by a mixture ofE3,Z13-18:Ac plusE2,Z13-18:OH (1∶),Microsphecia brosiformis by E3,Z13-18:Ac,Synanthedon conopiformis by the analogous alcohol,Synanthedon scoliaeformis andNemaxera betulinella byE2,Z13-18:Ac,Triaxomera fulvimitrella byZ3,Z13-18:Ac. An analogous alcohol component is essential for the attraction ofB. ichneumoniformis males. Inhibitors forB. romanovi, B. scopigera andB. zuwandica attraction were discovered. Preliminary data on attractants for six other species as well as on the diurnal rhythm of sexual activity of three species are presented. A new method for the stereoselective synthesis of 3,13-18:Ac/OH andE2,Z13-18:Ac/OH is described.

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C18 Dienes as attractants for eighteen clearwing (Sesiidae), tineid (Tineidae), and choreutid (Choreutidae) moth species

Būda¹,

Mäeorg

Karalius³

et al. 1993

J Chem Ecol

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Sequential alkynylation of ω-bromoalkyl triflates: facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones

2004

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A novel stereocontrolled synthesis of (z,z)-3,13-octadecadien-1-yl acetate, the sex pheromone of synanthedon species

Vinczer¹,

Baán²,

Novák³

et al. 1984

Tetrahedron Letters

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Pheromone synthesis. XXI. Synthesis of (Z,Z)-3,13-octadecadienyl acetate and its (E,Z)-isomer, the attractant for the cherrytree borer.

Cited by 5 publications

References 2 publications

C18 Dienes as attractants for eighteen clearwing (Sesiidae), tineid (Tineidae), and choreutid (Choreutidae) moth species

C18 Dienes as attractants for eighteen clearwing (Sesiidae), tineid (Tineidae), and choreutid (Choreutidae) moth species

Sequential alkynylation of ω-bromoalkyl triflates: facile access to unsymmetrical non-conjugated diynes including precursors to diene pheromones

A novel stereocontrolled synthesis of (z,z)-3,13-octadecadien-1-yl acetate, the sex pheromone of synanthedon species

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