Difluoropalmitic acids as potential inhibitors of the biosynthesis of the sex pheromone of the Egyptian armyworm Spodoptera littoralis--IV.
2,2-, 3,3- and 4,4-Difluoropalmitic acids (1-3) have been synthesized and fully characterized. Acids 2 and 3 were prepared through fluorination of the corresponding dithioacetal-protected ketoesters followed by enzymatic saponification. The acids 1-3 were evaluated in vivo as inhibitors of the beta-oxidation step of the biosynthesis of (Z,E)-9,11-tetradecadienyl acetate, the major component of the sex pheromone of the Egyptian armyworm Spodoptera littoralis. Only, the 2,2- and 3,3-derivatives, i.e. those containing the two fluorine atoms at the positions involved in the chain-shortened step, have been found to be active, the activity being similar to or lower than that displayed by the corresponding monofluorinated acids.
Bosch
M P
MP
Department of Technology of Tensioactives, C.I.D. (CSIC), Barcelona, Spain.
Pérez
R
R
Lahuerta
G
G
Hernanz
D
D
Camps
F
F
Guerrero
A
A
D000818:Animals; D004952:Esters / Q000378:metabolism; D005227:Fatty Acids / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010169:Palmitic Acids / Q000494:pharmacology*; D012724:Sex Attractants / Q000037:antagonists & inhibitors / Q000096:biosynthesis*; D017550:Spectroscopy, Fourier Transform Infrared; D018411:Spodoptera / Q000187:drug effects / Q000378:metabolism*
C101382:2,2-difluoropalmitic acid; C101381:3,3-difluoropalmitic acid; C101380:4,4-difluoropalmitic acid; D004952:Esters; D005227:Fatty Acids; D010169:Palmitic Acids; D012724:Sex Attractants