Metathesis synthesis of pheromones or their components

A metathesis and cross-metathesis technology, which is applied in the direction of metathesis reactions to produce hydrocarbons, compounds containing elements of group 5/15 of the periodic table, compounds containing elements of group 3/13 of the periodic table, etc., can solve the problem of expensive and easy-to-produce drug resistance And other issues
CN100528829CInactive Publication Date: 2009-08-19R·L·佩德森 +1
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
R·L·佩德森
Publication Date
2009-08-19
Estimated Expiration
Not applicable · inactive patent

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Abstract

The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, the major component of the Peach Twig Borer pheromone; (5R, 6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9, Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenyl formate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenyl acetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate, the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employ a Class I-IV metathesis catalyst, entail few reaction steps, use generally commercially available starting materials, and have relatively short process times. These syntheses produce good yields without the need for expensive or sophisticated equipment. The invention also provides an inexpensive route for producing omega-haloalkenols by cross-metathesizing alpha-omega-diacetoxy alkenes and alpha-omega-dihalides to yield omega-haloalkenols, which are easily converted into omega-haloalkanols under traditional hydrogenation methods.
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Description

technical field

[0001] The present invention relates to synthetic pheromones or components thereof, and in particular to metathesis reactions to prepare biologically active compounds and intermediates, such as insect attractant pheromones or components thereof, such as E-5-decenyl acetate , the main component of peach resin borer pheromone; (5R, 6S)-6-acetoxy-5-hexadecanolide (hexadecanolide), mosquito oviposition attractant pheromone; or E9, Z11-hexadecanolide Dienal (hexadecadienal), a pheromone in the larval moth of Hickory nut moth. Background of the invention

[0002] Insect pests destroy crops and / or spread disease. Common pest control methods include spraying crop fields, orchards, wetlands, forests, or other habitats of pests with insecticides. This approach is problematic because the pesticide is applied directly to the crop or water, a practice that is detrimental to the optimization of living species as well as water quality issues and other environmental consid...

Claims

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