Termites trail pheromone

Peppuy A., Robert A., Semon E., Ginies C., Lettere M., Bonnard O. and Bordereau C. (2001b) (Z)-dodec-3-en-l-ol, a novel termite trail pheromone identified after solid phase microextraction from Macrotermes annandalei. J. Insect Physiol. 47, 445 -53. 

Quennedey, A. (1977) An ultrastructural study of the polymorphic sternal gland in Reticulitermes santonensis (Isoptera, Rhinotermitidae) another way of looking at the true termite trail-pheromone. Proc. VIII Int. Cong. lUSSI, Pudoc, Wageningen. pp. 48-9. 

Kodama, M., Y. Matsuki, and S. Ito Syntheses of macrocyclic, terpenoids by intramolecular cyclization. I. (+)-Cembrene-A, a termite trail pheromone, and ( )-nephthenol. Tetrahedron Lett. 1975, 3065—3068. 

Recent trend in the synthesis of olefinic pheromones is the use of transition metal-catalyzed cross coupling reaction for carbon-carbon bond formation. Scheme 8 summarizes a synthesis of the termite trail marker pheromone, (3Z,6Z)-3,6-dodecadien- l-ol (2) by Oehlschlager [19]. The key-step is the palladium-catalyzed cross-coupling of allylic chloride A and alkenylalane B. 

The diterpene, Neocembrene A, or (l , 5A, 9A, 12i )-l,5,9-trimethyl-12-(l-methyl-ethenyl)-l,5,9-cyclotetradecatriene has been identified after SPME and GC-MS analysis as the major component of the trail-following pheromone of the Rhinotermitidae Prorhinotermitinae, Prorhinotermes canalifrons and P. simplex. In all other Rhinotermitidae studied so far, the major component of the trail pheromone has been dodecatrienol. Hydro-quinone was identified for the first time as a phagostimulating pheromone in the Australian termite species, Mastotermes darwiniensis. ... 

F. J. Ritter and C. J. Persoons, Trail Pheromones and Related Compounds in Termites and Ants. Proceedings of the Eighth Congress of lUSSI, p. 34. Pudoc, Wageningen, 1977. 

Dictyoptera. Notwithstanding the economic importance of termites and cockroaches, relatively few pheromones have been identified in species in this order. In the case of termites, most of the chemical research has been undertaken on trail pheromones, which are utilized for a variety of critical social functions, such as emigration and recruitment to nest breaks or food finds. 

The range of biological activity that has been recorded for 14-membered-ring diterpenoids is remarkably wide They were found to function as insect trail pheromones, termite allomones, neurotoxins, cytotoxins, and anti-inflammatory and antimitotic agents. 

J)-Cembrene A (59), isolated from termite, some plants, and soft coral successively, has been shown to be a highly active scent-trail pheromone. Cembrene... 

Trail pheromones of termites can be mimicked by traces of ballpoint pen ink (Chen et al. 1998). Bine Papermate ball point pens work best. The scent trail must be fresh. Provide such ballpoint pen ink trails that are just made, and 30, 60, 90 and 120 s old. 

From the oil of Santalum spicatum (R.Br.) A.DC., Birch et al have isolated the two isomeric dihydrofarnesenes (1) and (2). These two compounds, although not identical with the trail pheromone of the Nasutitermes species of termites, both exhibit similar specific trail activities. Cavill and Coggiola have reported that the photosensitized oxygenation of a-farnesene (3) yields the five allylic alcohols (4)—(8) after reduction of the corresponding hydroperoxides. A new... 

Cembranoids are present both in plants and animals. The majority of the cembranoids of plant origin was isolated from tobacco. Cembranoid diterpenes, which serve as a trail pheromone and defense secretions, have been obtained from termites Nasutitermes exitiosus [160], Trinervitermes bettonianus [161], and various species of Cubitermes [162] and the ant Monmorium pharaonis [163],... 

Compound 129 is a sex pheromone and 132 is a trail pheromone. A 21-membered ring macrolide, 20-icosanolide (Fig. 27,159), a 23-membered ring macrolide, 22-docosanolide (160), and a 25-membered ring macrolide, 24-tetracosanolide (161), are produced by various bee species and are female sex pheromones [188], Compounds 160 and 161 are also contained in defense secretions of termites, Armiter-mes spp. [189]. 

Termite trail-following pheromone. Produced by the fungi Lenzites trabea and Glaeophyllum trabeum. 

Trail markers are used almost exclusively by social insects, such as bees, ants, and termites. An insect that has located a new source of food returns to the nest, marking his trail by releasing these substmices. At the nest, recraitment is initiated by perception of these trail pheromones. Some representative trail pheromones are presented in Fig. 17c. 

Insects detect pheromones in surprisingly small amounts. Thus, male Bombyx mori begin to react when air contains as little as 100 molecules of the female sex pheromone per cm 210). The trail pheromone of the leaf cutting ant Atta texana, methyl-4-methyl-pyrrole-2-carboxyl-ate (46) is perceived at a concentration of 0,08 pg/cm, that is 3.48 molecules/cm 240), about the same as that recorded for the trail pheromone cw-3-cw-6-/ran5-8-dodecatrien-l-ol of Reticulitermes virgin-icus termite workers (47) 241). 

Matsumura, F., H.C. Coppel, and A. Tai Isolation and Identification of Termite Trail-Following Pheromone. Nature 219, 963-964 (1968). 

Constituents of the pheromones of bees and ants, respectively Trail pheromone of the termite Nasutitermes exitisosis... 

Leuthold, R. H. and Ltischer, M. (1974) An unusual caste polymorphism of the sternal gland and its trail pheromone production in the termite Trinervitermes bettonianus. Insectes Sociaux, 21, 335-42. 

Matsumara, F., Coppel, H. C. and Tai, A. (1968) Isolation and identification of a termite trail-following pheromone. Nature, 219, 963-4. 

---