Infection of ryegrass (Lolium perenne) by an endophytic fungus (Acremonium loliae) confers resistance against the Argentine stem weevil (Listronotus bonariensis). Extracts from ryegrass clones, infected and uninfected with A. loliae, were compared in a feeding choice bioassay, and several fractions were identified which affected stem weevil feeding behavior. One stem weevil feeding deterrent, peramine C12H17N5O, has been isolated from infected ryegrass and partially characterized as a basic indole derivative. Extracts from culturedA. loliae had no effect on stem weevil feeding behavior nor was peramine detected in the fungal cultures examined. Peramine and the other active substances are hydrophilic in contrast to the lipophilic properties reported for the neurotoxic lolitrems also isolated from ryegrass infected with A. loliae and associated with causing ryegrass staggers disorder in livestock. It is suggested that ryegrass staggers and stem weevil feeding deterrency may arise by different biochemical mechanisms.