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Inhibition of pheromone action in Sesamia nonagrioides by Haloacetate analogues
Authors:Magi Riba  Matilde Eizaguirre  Albert Sans  Carmen Quero  Angel Guerrero
Abstract:The electrophysiological activity of some halogenated analogues of the major component of the sex pheromone of the corn stalk borer Sesamia nonagrioides Lef. (1) is presented. The analogues comprise a series of fluoro-, chloro- and bromoacetate analogues 4 – 10 as well as trifluoromethyl ketone 11. The fluoro derivatives 4 – 6 displayed remarkable electro-antennogram (EAG) intrinsic activities in comparison with the parent acetate 1, while the remaining analogues elicited significantly lower response. The compounds have also been tested as inhibitors of the sex pheromone perception in EAG and in the field. In the laboratory. fluoro analogues 4 – 6 were better inhibitors than chloro derivatives 7 – 9 , which in turn behaved similarly to the bromoacetate 10 . Trifluoromethyl ketone 11, however, was a poor inhibitor of the pheromone action. In the field, baits of mixtures of compounds 5 – 11 with the corn stalk borer pheromone in 10 :1 ratio inhibited the concomitant attraction of the clover cutworm moth Scotogramma irifolii Rott., while the difluoro analogue 5, trichloroacetate 9 and trifluoromethyl ketone 11 also diminished the number of catches of the armyworm Mythimna unipuncta Haw. The monofluoroacetate 4. trifluoro analogue 6 and bromo derivative 10 significantly disrupted the pheromone action of the corn borer, whereas trifluoromethyl ketone 11 synergistically increased the number of males attracted to the pheromone trap alone. Addition of 11 to baits containing the corn borer pheromone caught S. nonagrioides selectively with regard to the other habitat-sharing species M. unipuncta and S. trifolii.
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