2-(3-phenoxbenzoyl)-2-propyl ester of tralomethrin: A new derivative of synthetic pyrethroids
2006
Marzouk, M.A. (Alexandria Univ. (Egypt). Dept. of Pest Control and Environmental Protection)
The alpha-cyano-3-phenoxybenzyl ester of tralomethrin reacts readily with acetone at the benzilic position of the alcohol moiety in the presence of Na2CO3 to produce 2-(3-Phenoxybenzoyl)-2-propyl ester (Tralomethrin acetoune derivative) in crystalline form. The yield product of the new derivative was 97.4%. The spectrometry, using N.M.R, I.R and GC/M.S technique was carried out to confirm the chemical structure of the acetone derivative. The N.M.R. spectra for the derivative showed the loss of CHCN group at 6.32 ppm of the benzilic carbon (alcohol moiety) and an addition of two methyl groups from acetone molecule at 0.74 and 1.13 ppm. The I.R spectra established the presence of both ester and Ketone carbonyl bands at 1715 and 1680 cm-1 respectively. The GC/MS Fragmentation patterns confirmed the spectral data of N.M.R and I.R, However tralomethrin acetone derivative gave a single peak at tR=10.65 min., while the parent compound gave a single peak at tR=7.13 min. In addition, the fragmentation products confirmed the derivatization at the benzilic position of the alcohol moiety. The synthesis technique exhibited that tralomethrin reacts with the acetone molecule to give tralomethrin acetone adduct in the mechanism of kinetic acidic proton exchange.
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