Pheromones codling moth

Diene alcohol (38) is the pheromone of the codling moth, tlie creature responsible for the grubs in apples, and of the various possible disconnections (a) is best as it gives most simplification and a stabilised ylid (39) which will produce the requi red trans double bond. Allylic bromide (40) and aldehyde-ester (41) are available,... 

The compound shown below is a constituent of the pheromone of the codling moth. It has been synthesized using u-propyl bromide, propyne, 1-pentyne,... 

Pheromones Multiple products Codling moth, oriental fruit moth Various fruits and vegetables Insecticide... 

An alternative approach to the synthesis of 1,3-dienes is by elimination of benzene-sulphinic acid from homoallylic sulphones under basic conditions. This method has been used for the synthesis of a pheromone constituent of the codling moth (equation 67)109. 

The larval aggregation pheromone of the codling moth, Cydia pomonella L. (Lepidoptera Olethreutidae), was shown to be a blend of (E)-2-octenal, (E )-2-nonenal, sulcatone and geranyl acetone in combination with either 3-carene and/or three saturated aldehydes (octanal, nonanal, decanal). 

The compound shown below is a constitutent of the pheromone of the codling moth. It has been synthesized using n-propyl bromide, propyne, 1-pentyne, ethylene oxide, and C02 as the source of the carbon atoms. Devise a route for such a synthesis. Hint Extensive use of the chemistry of organocopper reagents is the basis for the existing synthesis. 

Combining the two partial structures, we obtain for the full structure of the codling moth s sex pheromone... 

Lofstedt C. and Bengtsson M. (1988) Sex pheromone biosynthesis of (E,E)-8,10-dodecadienol in codling moth Cydia pomonella involves E9 desaturation. J. Chem. Ecol. 14, 903-915. 

Other pheromones prepared using CM include 11 -tetradeceny 1 acetate (Omnivorous Leafroller), 8,10-dodecadienol (Codling Moth), 9-tetradecenyl formate (Diamondback Moth),47 9,11-hexadec-adienal (Pecan Nut Casebearer),48 and 4-tridecenyl acetate (Tomato Pinworm)49... 

This reaction was used in a synthesis of the sex pheromone (1) of the false codling moth. 

Some growers use pheromone traps to capture male codling moths and other pests... 

The most effective application technique for lepidopteran species is to permeate the atmosphere with synthetic pheromone, and to thereby prevent olfactory communication and mate finding. The mating disruption technique has been successfully applied in Europe to three lepidopteran insects from horticultural crops codling moth Cydia pomonella, and the grape berry moths Eupoecilia ambiguella and Lobesia botrana [132, 133]. 

Recognition of possible synthons in a target molecule is the most important factor to make its synthesis simple or complicated. Let us compare the efficiency and simplicity of three different syntheses of (8 ,10 )-8,10-dodecadien-l-ol (11), the female-produced sex pheromone of the codling moth, Cydia pomonella. This moth is a notorious pest of apple orchards. 

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