Pheromones pink bollworm moth

Pi oblem The pheromone gossyplure (21) of the pink bollworm moth is a mixture of double bond isomers at bond (a). The c-is double bond (b) can be made from an acetylene so disconnection (24c) is suggested, Hou would you make both cis and trans (23) ... 

Collins, R. D. and Carde, R. T. (1985). Variation in and heritability of aspects of pheromone production in the pink bollworm moth, Pectinophora gossypiella (Lepidoptera Gelechiidae). Annals of the Entomological Society of America 78 229-234. 

Haynes, K. F. and Baker, T. C. (1988). Potential for evolution of resistance to pheromones worldwide and local variation in chemical communication system of the pink bollworm moth, Pectinophora gossypiella. Journal of Chemical Ecology 14 1547-1560. 

Linn, . E., Jr and Roelofs, W. L. (1985). Response specificity of male pink bollworm moths to different blends and dosages of sex pheromone. Journal of Chemical Ecology 11 1583-1590. 

Gossyplure (sex pheromone of pink bollworm moth, a severe cotton pest)... 

The bioassay chambers were constructed of 6.4 mm plexiglass, 0.60 X 0.60 X 2.4 meters in dimension. The air inlet end was fitted with a charcoal filter through which air was drawn through the chamber by a variable velocity fan. The formulations to be tested were applied to growing cotton plants and allowed to age for the desired length of time. The treated plants were positioned at the air inlet end of the ch lmber and the airflow adjusted to approximately 3-5 km/hr. Male pink bollworm moths were positioned at the opposite end of the chamber, downwind of the pheromone source. Moth mortality was recorded versus an untreated control plant to compensate for any natural mortality. Table I summarizes the data from the test designed to demonstrate the attracticide effect. As can be seen, significant mortality is obtained only in the case where pheromone and toxicant are both present. 

The female pheromone of the gypsy moth was claimed to be gyptol (A, Table 7.2), while the true pheromone was disparlure (85). Although the female pheromone of the American cockroach was claimed to be a cyclopropane compound B, the genuine and major pheromone was periplanone-B. The female pheromone of the pink bollworm moth was proposed as propylure (C), while the genuine pheromone was gossyplure as a mixture of two isomers. In these three cases, the synthetic compounds with the false... 

Jacobson (1969) has separated a mixture of the cis and trans forms of propylure (10-propyl-fru/is-5,9-tridecadienyl acetate) (CXXIXX the sex pheromone of the female pink bollworm moth (Pectinophora gossypiella (Saunders)), into its pure isomers by thin-layer chromatography. The infrared spectrum of the separated frans-propylure had a medium band at 965 cm trans HC=CH) that was absent in the spectrum of the cis isomer. The spectrum of cis-propylure had an inflection at 740 cm. c/s-Propylure inhibited or masked the activity of the trans isomer, as... 

We have realized total synthesis of 7Z,llZ-hexadecadienyl acetate and 7Z,11E-hexadecadienyl acetate - sex pheromone of pink bollworm moth (Pectinophora gossypiella) via cometathesis of COD with 1-hexene (Scheme 4). 

As far as we know, there are only four publications devoted to cometathesis of COD with 1-hexene for pheromone synthesis of pink bollworm moth Pectinophora gossypiella) [31-34]. In 1973 Hammel et al recognized that a sex pheromone of this pest is a blend of 7Z,1 IZ-hexadecadienyl acetate and its corresponding Z,E-isomer [35]. It was shown later that the isomer ratio produced by the insect females depends on the geographic area of habitants. As a rule the natural content of Z,Z-isomer is about 56-62% [36-38]. Haynes et al found that the effectiveness of the action of artificial sex... 

In another work, the pheromone treatment reduced catches of the male pink bollworm moths in pheromone-baited traps, boll infestations, and female mating. The effect was compared to both the use of insecticide control and an untreated check plot.22 These flakes, alone or in combination, were sprayed and dispensed by air either in flake form or in a liquid formulation. The effectiveness of the gossyplure-treated flakes is seen in Figure 3. 

Nonconjugated dienes have been identified as sex pheromones from a variety of species, including the pink bollworm moth (Pectinophora gossypiella). The initially assigned structure was that of the branched diene (5) (see p. 15). Numerous syntheses of this molecule have been reported and are reviewed by Katzenellenbogen (59). The pheromone is now known (79) to be a 1 1 mixture of (7Z,11Z)- and (7Z,11 )-7,11-hexadecadien-l-yl acetate (529a and 529b, respectively, see Scheme 91). 

Small-scale field trials with fully stabilised micro-encapsulated formulations were carried out in Egypt during 1980 on two cotton pests - pink bollworm, Peotinophora gossypiella, and the Egyptian cotton leafworm, Spodoptera littoralis. Plots of 10 n x 10m were sprayed with the formulation and there were three replicates of each treatment. A plastic funnel trap (3) baited with synthetic pheromone was positioned at the centre of each plot. The effectiveness and persistence of communication disruption were measured by the reduction in catches of male moths in the traps in the treated plots relative to the catches in similar traps in untreated, control plots. 

At present the majority of pheromones used are those involving control and monitoring of Lepidoptera such as pink bollworm Pectinophora gossypiella, the oriental fruit moth Grapholita molesta and the tomato pinworm Keiferia lycopersicella. The advantage of a sex pheromone used against these species is that often there is quite an extensive range over which the pheromone can be effective. However, on the downside is the fact that only males are trapped. This means that it is... 

Scientists are interested in synthesizing pheromones to use as nontoxic alternatives to pesticides. When placed in a trap, bombykol can be used to capture male silkworm moths. When a synthetic pheromone is released in a field, the males cannot locate the females, which disrupts the reproductive cycle. This technique has been successful with controlling the oriental fruit moth, the grapevine moth, and the pink bollworm. 

Another company (624, 625) supplies a controlled release dispenser, which is a three-layer plastic laminated sheet consisting of a bottom protective layer, a middle pheromone reservoir layer, and a top permeable layer through which the pheromone diffuses. The sheet can be cut into ribbons and applied over an area. Formulations have been field tested on a number of insect pests gypsy moth, pink bollworm, peachtree borer, lesser peach tree borer, soybean looper, cabbage looper, European elm bark beetle, tobacco budworm, fall armyworm, tussock moth, eastern spruce budworm, and Mediterranean fruit fly. 

Gaston, L. K., R. S. Kaae, H. H. Shorey, and D. Sellers Controlling the pink bollworm by disrupting sex pheromone communication between adult moths. Science 196,904—905 (1977). 

Example 19.1-2 Bollworm pheromones You have been using 1.0-mm-diameter microcapsules filled with a saturated solution of the pheromone gossyplure, for the pink bollworm. When the capsules contain excess solid pheromone, they attract bollworm moths into insecticide-loaded traps for 27 days. 

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