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Introduction
The Asian corn borer (ACB), Ostrinia furnacalis, is a major pest of corn that causes significant economic losses in agriculture. The use of insecticides to control ACB has led to the development of resistance, as well as environmental and health concerns. One alternative approach to reduce ACB populations is through the use of insect sex pheromones, which have proven to be effective in disrupting ACB mate location and reducing their reproductive potential. In this paper, we propose a new method for synthesizing ACB sex pheromones, specifically focusing on the synthesis of the ACB female sex pheromone, (E)-12-tetradecenyl acetate.
Synthesis of the ACB sex pheromone
The ACB female sex pheromone, (E)-12-tetradecenyl acetate, is composed of a 14-carbon chain that contains a double bond at the 12th carbon, and an acetate group at the end of the chain. The synthesis of this sex pheromone requires the preparation of the 14-carbon chain with the required functional groups and stereochemistry, followed by the addition of the acetate group.
The first step in the synthesis of the sex pheromone is the preparation of the 14-carbon chain, which can be achieved through several different methods. One method involves the use of Wittig-type reactions, in which a phosphorus ylide reacts with an aldehyde to produce a carbon-carbon double bond. The reaction between 1-bromo-12-tetradecene and triphenylphosphine followed by treatment with methylene triphenylphosphorane produces (E)-12-tetradecenylphosphonium bromide. Treatment of this intermediate with sodium hydroxide produces (E)-12-tetradecen-1-ol, which is then oxidized to the corresponding aldehyde with the use of PCC (pyridinium chlorochromate). Alternatively, the aldehyde can be synthesized through the use of olefin metathesis, followed by oxidation of the resulting alcohol. The stereochemistry of the double bond can be established through the use of chiral reagents or catalysts.
After the preparation of the 14-carbon chain, the acetate group can be added through the use of acetic anhydride and a catalyst such as pyridine or DMAP (4-dimethylaminopyridine). The reaction produces the final product, (E)-12-tetradecenyl acetate, which can be purified through column chromatography or distillation.
Conclusion
The synthesis of the ACB female sex pheromone, (E)-12-tetradecenyl acetate, is an important step towards developing effective and environmentally friendly methods for controlling ACB populations in agriculture. By disrupting the mate location and reproductive potential of ACB, insect sex pheromones provide an alternative to the use of insecticides, which have negative impacts on human health and the environment. The proposed method for synthesizing the ACB sex pheromone relies on established synthetic techniques, and can be further optimized to produce high yields of pure product. With further development, this method may prove to be a valuable tool for reducing ACB populations and improving the sustainability of agricultural practices.