(Z)-9-Nonadecene

Gland Origin and Electroantennogram Activity of Volatile Compounds in Ghost Ants, Tapinoma melanocephalum (Hymenoptera: Formicidae) and Behavioral Response to (Z)-9-Nonadecene.[Pubmed:29099928]

Environ Entomol. 2017 Dec 8;46(6):1374-1380.

Volatile compounds in Tapinoma melanocephalum (Fabricius) (Hymenoptera: Formicidae, Dolichoderinae) workers were analyzed using gas chromatography-mass spectrometry and electroantennogram responses of workers to these compounds were investigated using coupled gas chromatography-electroantennographic detection. Among 18 detected compounds, six elicited electroantennogram response, including 6-methyl-5-hepten-2-one, 4 iridodials, and (Z)-9-Nonadecene. (Z)-9-Nonadecene and iridodials were identified the first time in T. melanocephalum. (Z)-9-Nonadecene is a major component in mandibular glands and iridodials are produced in pygidial glands. In contrast to previous report, actinidine was not found in pygidial glands. Behavioral response of workers to the synthetic (Z)-9-Nonadecene was investigated. (Z)-9-Nonadecene is an attractant to T. melanocephalum. It also affected their locomotion patterns.

Analysis of anal secretions from phlaeothripine thrips.[Pubmed:15112732]

J Chem Ecol. 2004 Feb;30(2):409-23.

The anal secretions of 16 phlaeothripine thrips species (Thysanoptera: Phlaeothripidae) were studied, including a reinvestigation of three species previously reported. A total of 37 components were detected, including hydrocarbons, acetates, terpenes, carboxylic acids, a quinone, an aromatic compound, and a pyranone compound. The secretions of all species were composed of some of these components, with Xylaplothrips inquilinus possessing as many as 11 components. Of these components, (Z)-9-octadecene, (Z)-9-Nonadecene, nonadecadiene, octanoic acid, decanoic acid, geranial, neral, alpha-pinene, beta-pinene, caryophyllene, 2-hydroxy-6-methylbenzaldehyde, and two unidentified monoterpenes [UK-I (M+136) and UK-II (M+168)] were detected for the first time. The chemicals were species-specific; four Liothrips species and three Holothrips species could be distinguished from each other and their congeners by the GC profiles of the ether extracts of their anal secretions. The anal secretions of gall-inducing thrips commonly contained terpenes. of which citral (a mixture of geranial and neral) and beta-acaridial repelled ants or had antifungal activity. The findings suggest that these terpenes play a defensive role and prevent galls from fungal infestation. 3-Butanoyl-4-hydroxy-6-methyl-2H-pyran-2-one, found from three Holothrips spp., caused paralysis in ants. Chemical analysis of anal secretion components is a useful method for the classification of tubuliferan species that are difficult to distinguish on the basis of morphological characters.

Leaf-cutting antAtta laevigata (Formicidae: Attini) marks its territory with colony-specific dufour gland secretion.[Pubmed:24254908]

J Chem Ecol. 1992 Feb;18(2):183-96.

The workers of the leaf-cutting antAtta laevigata were found to mark a territory around their nest and along trunk trails. Elsewhere, we reported that the territorial mark had orientation and agonistic functions. The presence of this mark induced an alarm behavior in intruder workers and stimulated the residents' aggressiveness. Of the parts of the body tested, only the extracts from gaster or Dufour gland were able to induce the same agonistic behavior. The compoundsn-heptadecane, (Z)-9-Nonadecene, 8,11-nonadecadiene, and (Z)-9-tricosene, secreted by Dufour gland were identified on foraging trails in the field as components of the territorial odor.

Sabulodes caberata guenee (Lepidoptera: Geometridae) : Components of its sex pheromone gland.[Pubmed:24306671]

J Chem Ecol. 1986 Dec;12(12):2107-16.

A 6,9-nonadecadiene, (Z)-9-Nonadecene, andn-nonadecane were identified in extracts of sex pheromone glands of femaleSabulodes caberata Guenee. Potential pheromonal activity of gland components was assessed by electroantennogram measurements of gas-chromatographic fractions of abdominal tip extracts. Chemical identification was based on gas chromatography and mass spectrometry of parent compounds, hydrogenation products, ozonolysis products, dimethyl disulfide adducts, and synthesis. The monoene was synthesized via coupling of alkyl and acetylenic intermediates. (Z,Z)-6,9-Nonadecadiene (Z6,Z9-19ratioH) was synthesized from methyl linoleate via chain lengthening. SyntheticZ6,Z9-19ratioH had the same retention times on polar and nonpolar capillary gas-chromatographic columns as the 6,9-nonadecadiene from the sex pheromone glands. In field testsZ6,Z9-19:H alone produced trap catch of maleS. caberata and addition of (Z)-9-Nonadecene orn-nonadecane had no effect on trap catch.