Sex pheromone of the European grapevine moth, Lobesia botrana Schiff. (Lepidoptera: Tortricidae): Synthesis and effect of isomeric purity on biological activity

R. Ideses; J. T. Klug; A. Shani; S. Gothilf; E. Gurevitz

doi:10.1007/BF00984016

Sex pheromone of the European grapevine moth, Lobesia botrana Schiff. (Lepidoptera: Tortricidae): Synthesis and effect of isomeric purity on biological activity

R. Ideses, J. T. Klug, A. Shani, S. Gothilf, E. Gurevitz

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

A short synthesis of (E, Z)-7,9-dodecadien-1-yl acetate from propargyl alcohol and 6-bromohexanol via acetylenic-allenic isomerization of the resulting bis-THP-1,9-non-2-yn-diol is described. The field test of several preparations showed that the E,E isomer does not interfere with the biological activity of the pheromone. It was found that the "crude" preparation has higher activity than purified pheromone or virgin females.

Original language	English
Pages (from-to)	195-200
Number of pages	6
Journal	Journal of Chemical Ecology
Volume	8
Issue number	1
DOIs	https://doi.org/10.1007/BF00984016
State	Published - 1 Jan 1982

Keywords

(E,E)-7,9-dodecadien-1-yl acetate
(E,Z)-7
9-Dodecadien-1-yl acetate
European grapevine moth
Lepiadoptera
Lobesia botrana
Tortricidae
biological activity
purification
sex pheromone

ASJC Scopus subject areas

Ecology, Evolution, Behavior and Systematics
Biochemistry

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10.1007/BF00984016

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title = "Sex pheromone of the European grapevine moth, Lobesia botrana Schiff. (Lepidoptera: Tortricidae): Synthesis and effect of isomeric purity on biological activity",

abstract = "A short synthesis of (E, Z)-7,9-dodecadien-1-yl acetate from propargyl alcohol and 6-bromohexanol via acetylenic-allenic isomerization of the resulting bis-THP-1,9-non-2-yn-diol is described. The field test of several preparations showed that the E,E isomer does not interfere with the biological activity of the pheromone. It was found that the {"}crude{"} preparation has higher activity than purified pheromone or virgin females.",

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author = "R. Ideses and Klug, {J. T.} and A. Shani and S. Gothilf and E. Gurevitz",

year = "1982",

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T1 - Sex pheromone of the European grapevine moth, Lobesia botrana Schiff. (Lepidoptera: Tortricidae)

T2 - Synthesis and effect of isomeric purity on biological activity

AU - Ideses, R.

AU - Klug, J. T.

AU - Shani, A.

AU - Gothilf, S.

AU - Gurevitz, E.

PY - 1982/1/1

Y1 - 1982/1/1

N2 - A short synthesis of (E, Z)-7,9-dodecadien-1-yl acetate from propargyl alcohol and 6-bromohexanol via acetylenic-allenic isomerization of the resulting bis-THP-1,9-non-2-yn-diol is described. The field test of several preparations showed that the E,E isomer does not interfere with the biological activity of the pheromone. It was found that the "crude" preparation has higher activity than purified pheromone or virgin females.

AB - A short synthesis of (E, Z)-7,9-dodecadien-1-yl acetate from propargyl alcohol and 6-bromohexanol via acetylenic-allenic isomerization of the resulting bis-THP-1,9-non-2-yn-diol is described. The field test of several preparations showed that the E,E isomer does not interfere with the biological activity of the pheromone. It was found that the "crude" preparation has higher activity than purified pheromone or virgin females.

KW - (E,E)-7,9-dodecadien-1-yl acetate

KW - (E,Z)-7

KW - 9-Dodecadien-1-yl acetate

KW - European grapevine moth

KW - Lepiadoptera

KW - Lobesia botrana

KW - Tortricidae

KW - biological activity

KW - purification

KW - sex pheromone

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Sex pheromone of the European grapevine moth, Lobesia botrana Schiff. (Lepidoptera: Tortricidae): Synthesis and effect of isomeric purity on biological activity

Abstract

Keywords

ASJC Scopus subject areas

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