Methyl 6-methylsalicylate, trail pheromone of the ant Tetramorium impurum

Morgan, E. David; Ollett, D. G.

doi:10.1007/bf00368520

Cited by 21 publications

(8 citation statements)

References 9 publications

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“…This range included the~50 : 1 ratio found in analyses of the mandibular gland extracts. Methyl 6-methylsalicylate, the most abundant substance, has been previously reported to be involved in several communicative contexts in ant semiochemistry (Duffield and Blum, 1975;Longhurst et al, 1980;Morgan and Ollett, 1987;Kohl et al, 2000;Ayasse et al, 2001). In contrast, 3-ethyl-4-methylpentanol has been reported from only a few ant species (Francke et al, 1985;do Nascimento et al, 1993;Greenberg et al, 2004Greenberg et al, , 2007.…”

Section: Discussionmentioning

confidence: 96%

Chemical communication in mating behaviour of the slave-making ant Polyergus rufescens (Hymenoptera, Formicidae): 3-ethyl-4-methylpentanol as a critical component of the queen sex pheromone

et al. 2008

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The aim of the research reported here was to determine whether 3-ethyl-4-methylpentanol, a minor but crucial component of the sex pheromone of the North American slave-making ant species Polyergus breviceps, was also a component of the sex pheromone of the European congener Polyergus rufescens. Thus, the contents of mandibular glands of P. rufescens virgin queen were extracted and analysed. The main component of the extracts was methyl 6-methylsalicylate and 3-ethyl-4-methylpentanol was identified as one of several minor components. Further analyses showed that the insects produce mainly the (R)-enantiomer of the alcohol. Males responses to various blends of methyl 6-methylsalicylate with the racemate or the pure enantiomers of 3-ethyl-4-methylpentanol were tested in field behavioural bioassays. The data showed that blends of methyl 6-methylsalicylate and 3-ethyl-4-methylpentanol were strongly synergistic, with the most active ratios being biased toward the first component. The addition of other minor components to the binary blend neither increased nor decreased responses by males. Only the (R)-enantiomer of the alcohol was biologically active; its antipode did not inhibit attraction. The results are discussed in terms of the evolution of signals, and are compared with the results previously obtained for the allopatric species Polyergus breviceps.

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Section: Discussionmentioning

confidence: 96%

Chemical communication in mating behaviour of the slave-making ant Polyergus rufescens (Hymenoptera, Formicidae): 3-ethyl-4-methylpentanol as a critical component of the queen sex pheromone

et al. 2008

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“…Although methyl 6-methylsalicylate has been identified from more than 20 species of ants, its function is known for only a fraction of them. It acts as a sex pheromone in Polyergus breviceps and P. rufescens (Greenberg et al, 2004;Castracani et al, 2005); a trail pheromone in Tetramorium impurum and Mayriella overbecki (Morgan and Ollett, 1987;Kohl et al, 2000); and as an alarm pheromone in Gnamptogenys pleurodon (Duffield and Blum, 1975). Sometimes methyl 6-methylsalicylate is mixed with other compounds to elicit a response, such as in P. breviceps and P. rufescens (Greenberg et al, 2004;Castracani et al, 2008); or it is the only compound needed to elicit a sexual response, such as in P. rufescens (Castracani et al, 2005).…”

Section: Discussionmentioning

confidence: 98%

Methyl 6-Methylsalicylate: A Female-Produced Pheromone Component of the Parasitoid Wasp Spalangia endius

et al. 2010

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Sex-pheromone-related behavior and chemistry were studied in the wasp Spalangia endius Walker (Hymenoptera: Pteromalidae), a pupal parasitoid of the house fly, Musca domestica L. (Diptera: Muscidae). Males responded behaviorally to female extracts by arrestment, whereas females did not arrest to male extracts. In a comparison of male and female extracts by gas chromatography-mass spectrometry (GC-MS), two female-specific compounds were found. One was identified as methyl 6-methylsalicylate (gas chromatographic retention time and mass spectrum versus an authentic standard), but the chemical structure of the second compound is still unknown. Male antennae were sensitive to both compounds in electrophysiological tests (GC-EAD). Males responded behaviorally to methyl 6-methylsalicylate by arrestment, but did not arrest to the second compound. Methyl 6-methylsalicylate has been reported previously from some ant and beetle species, but never from the Pteromalidae. Chemical analysis of the extracts and the male behavioral results are consistent with the hypothesis that methyl 6-methylsalicylate functions as a female-emitted pheromone component at short range, but the exact role of both compounds in intersexual interactions in S. endius remains to be determined.

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“…Iridomyrmex humilis (Cavill et al 1979(Cavill et al , 1980Van Vorhis Key & Baker 1982a,b) Tetramorium impurum (Morgan & Ollett 1987;Morgan et al 1990) Lasius juliginosus (Huwyler et al 1975) Pristomyrmex pungens (Hayashi & Komae 1977)…”

Section: Alarm Pheromonesmentioning

confidence: 97%

Insect chemical communication: Pheromones and exocrine glands of ants

Jackson

Morgan

1993

Chemoecology

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Summary. Chemical communication plays a very important role in the lives of many social insects. Several different types of pheromones (species-specific chemical messengers) of ants have been described, particularly those involved in recruitment, recognition, territorial and alarm behaviours. Properties of pheromones include activity in minute quantities (thus requiring sensitive methods for chemical analysis) and specificity (which can have chemotaxonomic uses). Ants produce pheromones in various exocrine glands, such as the Dufour, poison, pygidial and mandibular glands. A wide range of substances have been identified from these glands.

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Methyl 6-methylsalicylate, trail pheromone of the ant Tetramorium impurum

Cited by 21 publications

References 9 publications

Chemical communication in mating behaviour of the slave-making ant Polyergus rufescens (Hymenoptera, Formicidae): 3-ethyl-4-methylpentanol as a critical component of the queen sex pheromone

Chemical communication in mating behaviour of the slave-making ant Polyergus rufescens (Hymenoptera, Formicidae): 3-ethyl-4-methylpentanol as a critical component of the queen sex pheromone

Methyl 6-Methylsalicylate: A Female-Produced Pheromone Component of the Parasitoid Wasp Spalangia endius

Insect chemical communication: Pheromones and exocrine glands of ants

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