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Haloacetate analogs of pheromones: Effects on catabolism and electrophysiology inPlutella xylostella

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Abstract

A series of mono-, di-, and trihalogenated acetate analogs of Zl 1–16: 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 halo-acetates were essentially inactive. The polar diazoacetate and the trifluoromethyl ketone were also very weak EAG stimulants. The effects of these analogs on the hydrolysis of [3H]Z11–16∶Ac to [3H]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 F2Ac > F3Ac > FAc > Ac > Cl2Ac > ClAc > Dza > Br2Ac > BrAc > Tfp > I > Cl3Ac > Br3Ac > 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 inP. xylostella males.

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  1. Department of Chemistry, State University of New York, 11794-3400, Stony Brook, New York

    Glenn D. Prestwich & Ludvik Streinz

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  1. Glenn D. Prestwich
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  2. Ludvik Streinz
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On leave from Institute of Organic Chemistry, Czechoslovak Academy of Science, Flemingovo naměstí 2, 16610, Prague, Czechoslovakia.

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Prestwich, G.D., Streinz, L. Haloacetate analogs of pheromones: Effects on catabolism and electrophysiology inPlutella xylostella . J Chem Ecol 14, 1003–1021 (1988). https://doi.org/10.1007/BF01018789

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  • DOI: https://doi.org/10.1007/BF01018789

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