Recent Development in Insect Pheromone Research, in Particular in the Netherlands

Abstract

A review is given of recent pheromone work carried out in the Netherlands on Lepidoptera, cockroaches, pharaoh's ants and termites, special emphasis being given to isolation and identification aspects. The sex pheromones of three leaf roller moths (Tortricidae) have been isolated, identified and field tested, viz. those of Adoxophyes orana (cis-9-tetradecenyl acetate (tda) and cis-I1-tda in the ratio 9:1), Clepsis spectrana (cis-9-tda:cis-11-tda, 1:3) and Archipspodana (cis-11-tda:trans-l1-tda, about 1:1). For ?ponomeuta, data have been obtained indicating a correlation between taxonomic groups and pheromone structure. Two sex pheromones (periplanone A and B) of the American cockroach, Periplaneta americana, have been isolated and partially identified. Their elementary formulas, C. 15H. 20O. 2 and C. 15H. 20O. 3, respectively, suggest that they are sesquiterpenoids, spectral data of periplanone B indicating that it has the germacrane skeleton. The aggregation pheromone of the German cockroach, Blattella germanica appears to be a complex mixture in which certain free acids play an important role. Three heterocyclic compounds have been isolated from Pharaoh's ants, Monomorium pharaonis. Monomorine I, C. 13H. 25N, is the first indolizine derivative found in the animal kingdom. Monomorine II, C. 13H. 27N, and monomorine III, C. 15H. 29N, are pyrrolidine derivatives. The three compounds are constituents of the odour trail and are present in excretions collected from the insect's sting. These excretions have a function in trail-following as well as in defense. In choice tests monomorine I and III act as attractants. Cis-3, cis-6, trans-8-dodecatrienol, initially identified as a trail pheromone of the termite Reticulitermes virginicus, was found to be a trail pheromone also for Reticulitermes santonensis. Eight dodecatrienol isomers were tested for activity towards this termite. In their ability to evoke trail-following behaviour as well as their attractancy in choice tests, they resemble each other qualitatively, but quantitatively, they show considerable differences. From fungus-infected wood a compound was isolated which effectively induces trail-following behaviour, and moreover, is a potent attractant. Its elementary formula, C. 15H. 24O, and the presence of acorane among its hydrogenation products, show that it is a sesquiterpenoid. Two other potent attractants for R. santonensis were found in wood oils: tricycloekasantalal, C. 12H. 13O in East-Indian sandalwood oil and dihydroagarofuran, C. 15H. 20O in West-Indian sandalwood oil. © 1974 BRILL.