Termites trail-following

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

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

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

Matsumura, F., K. Nishimoto, T. Ikeda, and H. C. Coppel Influence of carbon sources on the production of the termite trail-following substance by Gloephyllum trabeum. J. Chem. Ecol. 2, 299—305. 

Insect pheromonesy which serve to convey messages between insects, have been isolated from many species and found to be both highly specific, and effective in mere traces. They are usually aliphatic compounds, such as the termites trail-following substance, dodecatrien-i-ol, but that secreted by the town ant is methyl 4-methylpyrrole-2-carboxylate. 

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. ... 

C. (2007). Trail-following pheromones in basal termites, with special references to Mastotermes darwiniensis. J. Chem. Ecol., 33,1960-1977. 

Matsumura et al. (25) identified (Z,Z.,E)-3,6,8-dodecatrien-l-ol in extracts of the termite Reticulitermes flavipes and reported that this compound was a powerful releaser of trail following for workers. However, this compound is also produced by the fungus Lenzites trabea which infects the wood fed upon by R. flavipes. The significance of the dodecatrienol in the biology of this termite has recently been examined in considerable detail (26). 

Kaib, M., O. Bruisma, and R.H. Leuthold Trail Following in Termites Evidence for a Multicomponent System. J. Chem. Ecol. 8, 1193-1205 (1982). 

W.S. Eng, E. Deaton, and D. Wichern Structure-Activity among Aromatic Analogs of the Trail Following Pheromone of Subterranean Termites. J. Chem. Ecol. 10, 1201-1217 (1984). 

The blind snake Leptotyphlops dulcis is a specialized burrower that feeds on termites and ant brood. It follows the ant pheromone trails to find its prey (Section 12.1). when attacked by ants, this snake tilts its scales individually so that the skin appears silvery. While it writhes, it covers itself with feces and a clear viscous fluid, discharged from the anus. It may also assume a stationary coiled position. when it resumes searching and feeding, it is no longer attacked by ants. The effect lasts from 3 to 30 minutes (Gehlbach etal., 1968). Here a predatory species protects itself from the defensive actions of its prey. 

Blind snakes find their prey by using the prey s pheromones. The wormlike Texas blind snake, Leptotyphlops dulcis, of the southwestern United States leads a subterranean life and feeds on termites and ant brood. It finds ants by following their pheromone trails (Gehlbach etal, 1968). Other blind snakes such as the American blindsnake, Typhlops pusillus (Gehlbach et al, 1971), and the Australian blindsnake, Ramphotyphlops nigrescens (Webb and Shine, 1992), also follow odor trails of ants, their prey. Texas blind snakes are attracted to the simple alkaloid skatole (methyl indole Fig. 12.4), an amine with an unpleasant odor from the ant Neivamyrmex sp. (Watkins etal, 1969). 

Determine the cis-trans geometry around the double bonds in the following compound, a trail pheromone of termites. (The chain is numbered starting from the carbon atom with the hydroxyl group.) How many geometric isomers are possible for the structure ... 

Two syntheses of the trail pheromone, neocembrene (435), of Nasu-titermes spp. termites have been reported. Kodama et al. 185) (Scheme 78) prepared the allylic phenyl thioether (430) from trans,trans-gQX iny linalool (429). Terminal epoxidation of (430) followed by intromolecular cyclization, desulfurization, and dehydration led to (435). Kitahara et al. 186) cyclized fra 5-geranylgeranic acid chloride (436) with SnCU to afford chloroketone (437) (Scheme 79). Dehydrohalogenation of (437) and subsequent reduction of ketone (438) via acetate (441) gave neocembrene (435). 

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