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United States Department of Agriculture

Agricultural Research Service

Research Project: IDENTIFICATION AND PRACTICAL USE OF SEMIOCHEMICALS FOR THE MANAGEMENT OF AGRICULTURALLY IMPORTANT INSECTS Title: Preparation of Carpophilus Lugubris (Coleoptera: Nitidulidae) Aggregation Pheromone by Direct Aldehyde Homologation

Authors
item Petroski, Richard
item Bartelt, Robert

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: August 31, 2006
Publication Date: August 24, 2006
Citation: Petroski, R.J., Bartelt, R.J. 2006. Preparation of Carpophilus lugubris (Coleoptera: Nitidulidae) aggregation pheromone by direct aldehyde homologation [abstract]. First European Chemistry Congress. Paper No. N-PO-130, p. 337.

Technical Abstract: Direct two-carbon homologation of aldehydes to methyl- or ethyl-branched unsaturated aldehydes was accomplished with diethyl ethylformyl-2-phosphonate dimethylhydrazone and diethyl propylformyl-2-phosphonate dimethylhydrazone. The new phosphonate reagents and protected aldehyde products can be readily purified by distillation. Isolated yields of products are good to excellent. This new chemistry replaces the standard three-step aldehyde homologation route using Horner-Wadsworth-Emmons chemistry. The synthesis of the aggregation pheromone for the dusky sap beetle, Carpophilus lugubris Murray, was shortened from seven steps to just five steps, and the commercial viability of pheromone production was improved. The pheromone can be used to control an insect that causes damage to a wide variety of crops and also spreads oak wilt disease and other harmful microorganisms.

Last Modified: 12/22/2014
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