This review reports different syntheses of deltamethrinic acid, especially those originating from our laboratory. Deltamethrinic acid is a synthetic compound whose structure is inspired from those present in the flower head of the plant Chrysanthemum cinerariifolium. Its ester 'deltamethrin' exhibits an extremely high insecticidal activity (DDTx35.000) and an extremely low toxicity to mammals.
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Reprint of "Inspired by flowers: synthetic routes to scalemic deltamethrinic acid" [Bioorg. Med. Chem. 17 (2009) 2555-2575].
Bioorg Med Chem
June 2009
Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, Namur B-5000, Belgium.
This review reports different syntheses of deltamethrinic acid, especially those originating from our laboratory. Deltamethrinic acid is a synthetic compound whose structure is inspired from those present in the flower head of the plant Chrysanthemum cinerariifolium. Its ester 'deltamethrin' exhibits an extremely high insecticidal activity (DDTx35.
View Article and Find Full Text PDFInspired by flowers: synthetic routes to scalemic deltamethrinic acid.
Bioorg Med Chem
March 2009
Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, Namur B-5000, Belgium.
This review reports different syntheses of deltamethrinic acid, especially those originating from our laboratory. Deltamethrinic acid is a synthetic compound whose structure is inspired from those present in the flower head of the plant Chrysanthemum cinerariifolium. Its ester 'deltamethrin' exhibits an extremely high insecticidal activity (DDTx35.
View Article and Find Full Text PDFDiastereoselective bromination of compounds bearing a cyclohex-3-enol moiety: application to the enantioselective synthesis of (1R)-cis-deltamethrinic acid.
J Org Chem
December 2008
Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 rue de Bruxelles, Namur, B-5000, Belgium.
(1R)-cis-chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry. Some mechanistic aspect of the addition of bromine to the C,C double bond of 2,2,5,5-tetramethylcyclohex-3-enol is disclosed.
View Article and Find Full Text PDFInfluence of (hydroxy)alkylamino substituents on enantioseparation ability of single-isomer amino-beta-cyclodextrin derivatives in chiral capillary electrophoresis.
Electrophoresis
August 2004
Cyclolab Cyclodextrin R & D. Laboratory Ltd., Budapest, Hungary.
A family of single-isomer amino-beta-cyclodextrin (amino-beta-CD) derivatives containing an amino or (hydroxy)alkylamino group in one of the primary positions has been synthesized. The steric effect and hydrogen bond forming ability of the different substituents on enantioseparation of acidic enantiomers has been studied by capillary electrophoresis (CE). Three enantiomeric model compounds (mandelic acid, cis-permethrinic acid, and cis-deltamethrinic acid) having significantly different apparent complex stability constants with beta-CD were applied in the experiments.
View Article and Find Full Text PDFThermal decomposition and isomerization of cis-permethrin and beta-cypermethrin in the solid phase.
Pest Manag Sci
February 2002
Centro de Investigaciones de Plagas e Insecticidas (CIPEIN-CITEFA/CONICET), Zufriategui 4380, Villa Martelli (1603) Buenos Aires, Argentina.
The stability to heart of cis-permethrin and beta-cypermethrin in the solid phase was studied and the decomposition products identified. Samples heated at 210 degrees C in an oven in the dark showed that, in the absence of potassium chlorate (the salt present in smoke-generating formulations of these pyrethroids), cis-permethrin was not isomerized, although in the presence of that salt, decomposition was greater and thermal isomerization occurred. Other salts of the type KXO3 or NaXO3, with X being halogen or nitrogen, also led to a considerable thermal isomerization.
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