Haloacetate analogs of pheromones: effects on catabolism and electrophysiology in Plutella xylostella

Journal Article · Tue Mar 01 04:00:00 EST 1988 · J. Chem. Ecol.; (United States)

DOI:https://doi.org/10.1007/BF01018789· OSTI ID:6904931

Prestwich, G D; Streinz, L

A series of mono, di-, and trihalogenated acetate analogs of Z11-16:Ac were prepared and examined for electrophysiological activity in antennae of males of the diamondback moth, Plutella xylostella. In addition, two potential affinity labels, a diazoacetate (Dza) and a trifluoromethyl ketone (Tfp), were evaluated for EAG activity. The Z11-16:Ac showed the highest activity in EAG assays, followed by the fluorinated acetates, but other haloacetates were essentially inactive. The effects of these analogs on the hydrolysis of (/sup 3/H)Z11-16:Ac to (/sup 3/H)Z11-16:OH by antennal esterases was also examined. The three fluorinated acetates showed the greatest activity as inhibitors in competition assays, with rank order F/sub 2/Ac > F/sub 3/Ac > FAc > AC > Cl/sub 2/Ac > ClAc > Dza > Br/sub 2/Ac > BrAc > Tfp > I > Cl/sub 3/Ac > Br/sub 3/Ac > OH. The relative polarities of the haloacetates, as determined by TLC mobility, are in the order mono- > di- > trihalo, but F, Cl, Br, and I all confer similar polarities within a substitution group. Thus, the steric size appears to be the predominant parameter affecting the interactions of the haloacetate analogs with both receptor and catabolic proteins in P. xylostella males.

• Research Organization: State Univ. of New York, Stony Brook (USA)
• OSTI ID: 6904931
• Journal Information: J. Chem. Ecol.; (United States), Journal Name: J. Chem. Ecol.; (United States) Vol. 14:3; ISSN JCECD
• Country of Publication: United States
• Language: English

Related Subjects

550501* -- Metabolism-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ACETATES
ANIMALS
ARTHROPODS
CARBOXYLIC ACID SALTS
CATABOLISM
CHROMATOGRAPHY
ELECTROPHYSIOLOGY
ENZYME ACTIVITY
ENZYMES
ESTERASES
HYDROLASES
INHIBITION
INSECTS
INVERTEBRATES
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
LEPIDOPTERA
METABOLISM
MOTHS
PHEROMONE
PHYSIOLOGY
SECRETION
SEPARATION PROCESSES
THIN-LAYER CHROMATOGRAPHY
TRACER TECHNIQUES
TRITIUM COMPOUNDS