Leafrollers

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. 

Bacillus thuringiensis subsp. tenebrionis (Btt), potato leafroll vims (PLRV) Klebsiella pneumoniae subsp. ozaene, Bacillus thuringiensis var. kurstaki (Btk)... 

In moths, it was discovered in Helicoverpa zea that a peptide produced in the subesophageal ganglion portion of the brain complex regulates pheromone production in female moths (19). This factor has been purified and characterized in three species, Helicoverpa zea (20), Bombyx mori (21, 22), and Lymantria dispar (23). They are all a 33- or 34-amino acid peptide (named pheromone biosynthesis activating neuropeptide, PBAN) and have in common an amidated C-terminal 5-amino acid sequence (FXPRL-amide), which is the minimum peptide fragment required for pheromon-tropic activity. In the redbanded leafroller moth, it was shown that PBAN from the brain stimulates the release of a different peptide from the bursae copulatrix that is used to stimulate pheromone production in the pheromone gland found at the posterior tip of the abdomen (24). 

Nothofagus spp. Galangin (flavonol) and the stilbene Deter feeding by leafrollers 371... 

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. 

Foster, S. P., Clearwater, J. R., Muggleston, S. J., Dugdale, J. S. and Roelofs, W. L. (1986). Probable sibling species complexes within two described New Zealand leafroller moths. Naturwissenschaften 73 156-158. 

Hill, A.S.,Card6, R.T, Bode, W.M. and Roelofs, W.L. (1977). Sex pheromone components of the variegated leafroller moth, Platynota flavedana. Journal of Chemical Ecology 3 369-376. 

Thompson, D. R., Angerilli, N. R D., Vincent, C. and Gaunce, A. P. (1991). Evidence for regional differences in the response of the obliquebanded leafroller (Lepidoptera Tortricidae) to sex pheromone blends. Environmental Entomology 20 935-938. 

Roberts, I. M. and Harrison, B. D. (1979) Detection of potato leafroll and potato mop-top vimses by immunosorbent electron microscopy. Ann. Appl. Biol. 93, 289-297. 

Sefc, K. M., Leonhardt, W., and Steinkellner, H. (2000) Partial sequence identification of grapevine-leafroll-associated virus-1 and development of a highly sensitive IC-RT-PCR detection method. J. Virol. Methods 86, 101-106. 

Bjostad L. B. and Roelofs W. L. (1981) Sex pheromone biosynthesis from radiolabeled fatty acids in the redbanded leafroller moth. J. Biol. Chem. 256, 7936-7940. 

Foster S. P. and Roelofs W. L. (1988) Sex pheromone biosynthesis in the leafroller moth Planotortrix excessana by A10 desaturation. Arch. Insect Biochem. Physiol. 8, 1-9. 

Miller J. R. and Roelofs W. L. (1980) Individual variation in sex pheromone component ratios in two populations of the redbanded leafroller moth, Argyrotaenia velutinana. Envir. Entomol. 9, 359-363. 

Roelofs W. L., Du J.-W., Linn C. E., Glover T. J. and Bjostad L. B. (1986) The potential for genetic manipulation of the redbanded leafroller moth sex pheromone blend. In Evolutionary Genetics of Invertebrate Behavior, ed. M. D. Heuttel, pp. 263-272. Plenum Press, New York. 

Roelofs W. L. and Jurenka R. A. (1996) Biosynthetic enzymes regulating ratios of sex pheromone components in female redbanded leafroller moths. Bioorganic Med. Chem. Letters 4, 461 4-66. 

Molecular cloning and functional expression of desaturases from a primitive leafroller moth, Planotortrix octo, from New Zealand... 

The greenheaded leafroller moth, P. octo, utilizes a A10 desaturase in its pheromone biosynthetic pathway (Foster and Roelofs, 1988). A cDNA, designated Pocto-... 

Z11-14 Acid and 11-14 Acid are the only unsaturated pheromone intermediates of the redbanded leafroller moth, Argyrotaenia velutinana (Bjostad and Roelofs, 1981). Stable isotope experiments showed that the mixture of these unsaturated... 

Hao G., Liu W., O ConnorM. and Roelofs W. L. (2002) Acyl-CoAZ9- and ZlO-desaturase genes from a New Zealand leafroller moth species, Planotortrix octo. Insect Biochem. Molec. Biol. 32, 961-966. 

Oblique banded leafroller (Choristoneura rosaceana) S (11Z) tetradec-11-enyl acetate F (11E) tetradec-11-enyl acetate ... 

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... 

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