Pheromone omnivorous leafroller

Scheme 2. Synthesis of the mixture of 1IZ- and 1 lE-tetradecenyl acetates - sex pheromone omnivorous leafroller Archips podana).

In an article dealing with applications of olefin CM to a series of commercial products [138], solvent-free CM between ( )-3-hexene (produced by homocoupling of 1-butene) and 11-eicosenyl acetate 303 (produced from jojoba oil) was used to produce acetate 304 (Scheme 59), which is - as a natural 82 18 (EIZ) mixture - the pheromone of omnivorous leafroller, and serves as an environment-friendly pest controlling agent. The CM reaction was performed without solvent at 5 °C with a 4 1 mixture of ( )-3-hexene and 303, in the presence of only 0.2 mol% catalyst C, and furnished after 20 h coupling product 304 ( Z=83 17) in 50% yield. 

In some species, male variation in response to component ratio offset from the natural blend is somewhat modulated by ambient temperature (Linn et al, 1988). The response specificity of G. molesta and P. gossypiella to off-ratios of pheromone acetate components in a wind tunnel assay was narrower at 20 °C than at 26 °C. In the field, sexual activity in both species occurs at both of these temperatures, depending on time of year. Some field evidence of this phenomenon with P gossypiella appears in the distribution of catch in traps baited with a range of ratios measured at various times of the flight season. Flint et al. (1977) found an evidently narrower response breadth early in the season (when temperatures were cool) compared with late-season responses. In the omnivorous leafroller Platynota stultana, the optimum ratio of its two components for attraction seems to shift with temperature in the... 

Baker, J. L., Hill, A. S. and Roelofs, W. L. (1978). Seasonal variations in the pheromone trap catches of male omnivorous leafroller moths, Platynota stultana. Environmental Entomology 7 399 101. 

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... 

The omnivorous leafroller (OLR) feeds on a wide variety of fruits, vegetables, and ornamentals. Vineyards use pheromone traps to monitor the OLR populations and determine when control methods are needed. 

Webster, R.P., and R.T. Carde Relationship among Pheromone Titre, Calling and Age in the Omnivorous Leafroller Moth Platynota stultana). J. Insect Physiol. 28, 925-933 (1982). 

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