Haloacetate analogs of pheromones: effects on catabolism and electrophysiology in Plutella xylostella
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), Vol. 14:3
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ESTERASES
ENZYME ACTIVITY
MOTHS
ELECTROPHYSIOLOGY
PHEROMONE
CATABOLISM
ACETATES
INHIBITION
THIN-LAYER CHROMATOGRAPHY
TRACER TECHNIQUES
TRITIUM COMPOUNDS
ANIMALS
ARTHROPODS
CARBOXYLIC ACID SALTS
CHROMATOGRAPHY
ENZYMES
HYDROLASES
INSECTS
INVERTEBRATES
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
LEPIDOPTERA
METABOLISM
PHYSIOLOGY
SECRETION
SEPARATION PROCESSES
550501* - Metabolism- Tracer Techniques