STRUCTURE-ACTIVITY RELATIONSHIP OF ISOLATED AVENANTHRAMIDE ALKALOIDS AND SYNTHESIZED RELATED-COMPOUNDS AS OVIPOSITION DETERRENTS FOR PIERIS-BRASSICAE

The structure-activity relationship was investigated of compounds isol ated from the eggs of Pieris brassicae, the large white cabbage butter fly, and eight synthesized related compounds as oviposition deterrents for this insect. The activity of all compounds was tested in a dual-c hoice bioassay. The two most active oviposition deterrents for P. bras sicae were trans-2-[3-(4-hydroxyphenylpropenoyl)amino]-3,5- acid [8] a nd ans-2-[3-(3,4-dihydroxyphenylpropenoyl)amino]-3,5- dihyroxybenzoic acid [2]. Among members of this compound class, alteration of the subs tituents of the cinnamic acid part of the molecule affected the ovipos ition deterrent activity more profoundly than other structural changes . Modification of the anthranilic acid part of the molecule resulted i n lower activity.