Ho

5-propylresorcinol

5-pentylresorcinol oh ch3

5-pentylresorcinol oh ch3

mellein ch3 ch3

8-hydroxyisocoumarin 2,3-dimethytphenol 2-methyl-5-ethylphenol oh oh

CI CI

CI CI

2,6-dichlorophenol guaiacol, 2-methoxyphenol or catechol monomethyl ether

2,6-dichlorophenol

Figure 8.10 Phenols and resorcinols from metapleural glands of an ant and from defensive glands of millipedes and opilionids. Their function is undetermined but is probably antibiotic and defensive. 2,6-Dichlorophenol is the sexualpheromone of a number of species of ticks a sexual pheromone. They incorporated 36C1 from Na36Cl into the pheromone, presumably by chlorination of tyrosine or another precursor. In all, 14 species from five genera of ticks use this one compound as a female-produced sexual attractant. The tick Amblyomma variegatum on the other hand uses o-nitrophenol, methyl salicylate and nonanoic acid (ratio 2:1:8 fig per female). The biosynthesis in ventral glands has been demonstrated to occur after feeding, but the source of the compounds has not been studied.

It is known that primitive insects like Collembola (springtails) do produce pheromones, but so far only the alarm pheromone of Neanura muscorum has been identified as 1,3-dimethoxybenzene. Its origin is unknown. Other simple aromatic compounds like 2,4-dimethoxyaniline, phenol and 2-aminophenol were also found in whole body extracts.

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