NDLI: A convenient route for synthesis of 2-isopropyliden-5-methyl-4-hexen-1-yl butyrate, the sex pheromone of Planococcus kraunhiae (Hemiptera: Pseudococcidae), by use of β,γ to α,β double-bond migration in an unsaturated aldehyde

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A convenient route for synthesis of 2-isopropyliden-5-methyl-4-hexen-1-yl butyrate, the sex pheromone of Planococcus kraunhiae (Hemiptera: Pseudococcidae), by use of β,γ to α,β double-bond migration in an unsaturated aldehyde

Applied Entomology and Zoology : Volume 48, Issue 1, February 2013

Applied Entomology and Zoology : Volume 47

Applied Entomology and Zoology : Volume 46

A convenient route for synthesis of 2-isopropyliden-5-methyl-4-hexen-1-yl butyrate, the sex pheromone of Planococcus kraunhiae (Hemiptera: Pseudococcidae), by use of β,γ to α,β double-bond migration in an unsaturated aldehyde

Content Provider	Springer Nature Link
Author	Tabata, Jun
Copyright Year	2013
Abstract	The Japanese mealybug Planococcus kraunhiae (Kuwana) is an important pest which spoils many kinds of fruit in Japan. Because conventional application of insecticides is often ineffective, alternative strategies are being investigated for management of this pest. Recent studies revealed that a pheromone-based technique which interferes with sexual communication, i.e. mating disruption, was promising. However, mating disruption usually requires a substantial amount of a pheromone. I therefore developed a new and convenient route for synthesis of the P. kraunhiae pheromone, 2-isopropyliden-5-methyl-4-hexen-1-yl butyrate (fujikonyl butyrate). First, a commercially available isomer of fujikonol, 2-isopropenyl-5-methyl-4-hexen-1-ol (lavandulol), was oxidized, furnishing the corresponding aldehyde (lavandulal). The β,γ double bond of lavandulal smoothly migrated to the α,β position in the presence of acids, and as a consequence, the corresponding aldehyde of fujikonol (fujikonal) was obtained. Fujikonal was then reduced to fujikonol, which was esterified with butyric acid to give the pheromone of P. kraunhiae. All the reactions were accomplished under very mild conditions (room temperature to 50 °C) with good yields. Moreover, only small amounts of by-products were generated. The synthetic pheromone obtained by this method can be used as a mating disruptant.
Starting Page	229
Ending Page	232
Page Count	4
File Format	PDF
ISSN	00036862
Journal	Applied Entomology and Zoology
Volume Number	48
Issue Number	2
e-ISSN	1347605X
Language	English
Publisher	Springer Japan
Publisher Date	2013-03-17
Publisher Place	Japan
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Mealybug pheromone synthesis Double-bond migration 2-Isopropyliden-5-methyl-4-hexen-1-yl butyrate (fujikonyl butyrate) 2-Isopropenyl-5-methyl-4-hexen-1-ol (lavandulol) Entomology Agriculture Applied Ecology Plant Pathology Zoology Environmental Management
Content Type	Text
Resource Type	Article
Subject	Insect Science

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A convenient route for synthesis of 2-isopropyliden-5-methyl-4-hexen-1-yl butyrate, the sex pheromone of Planococcus kraunhiae (Hemiptera: Pseudococcidae), by use of β,γ to α,β double-bond migration in an unsaturated aldehyde

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