Tetradecenyl acetates

Identification of compounds in volatiles collected from hunting M. cornigera revealed three common components of moth sex pheromone blends (Z)-9-tetradecenal, (Z)-9-tetradecenyl acetate, and (Z)-ll-hexade-cenal [while there was insufficient material for mass spectrometry, gas chromatographic retention time evidence suggests that (Z)-ll-hexadece-... 

FIGURE 2 Relative proportions of three identified components of M. comigera spider volatiles (47). The variation in the ratios suggests that spiders change the moth-attracting blends they produce. Z11-16 AL, (Z)-ll-hexadecenal Z9-14-.AC, (Z)-9-tetradecenyl acetate Z9-14 AL, (Z)-9-tetradecenal. 

Collections of volatiles released by female carpenterworm moths, Cossus insularis (Lepidoptera Cossidae), showed that two compounds elicited EAG responses from the antennae of male moths. These compounds were identified as (E)-3-tetradecenyl acetate and (Z )-3-tetradecenyl acetate in a ratio of 95 5 respectively. ... 

The female sex pheromone of the cranberry blossom worm, Epiglaea apiata Grote (Lepidoptera Noctuidae), was identified as a blend of Z)-9-hexadecenyl acetate, (Z )-9-tetradecenyl acetate, and tetradeceyl acetate. They were present in the ratio of 65 2 33 respectively in the female pheromone gland. 

The female sex pheromone of the leaf-miner Phyllonorycter platini Staudinger (Lepidoptera Gracillariidae) has been identified as (Z IO)-tetradecenyl acetate. Activity of the synthetic compound was confirmed by field tests. ... 

The extracts of the female sex pheromone gland of the sandthorn car-penterworm moth, Holcocerus hippophaecolus Hua (Lepidoptera Cossi-dae), were found to contain ( )-3-tetradecenyl acetate, (Z )-3-tetradecenyl acetate, (Z )-7-tetradecenyl acetate, the corresponding alcohols and E)-9-tetradecenyl acetate. A combination of field trials and experiments were done to conclude that the sex pheromone of H. hippophaecolus is composed of (Z )-7-tetradecenyl acetate and (T)-3-tetradecenyl acetate. Optimal ratios and doses of these two and the possible role of other minor components remain to be determined. 

The sex pheromone of the South American tortricid moth, Argy-rotaenia sphaleropa, was identified as a mixture of (Z)-l 1-tetradecenal, (Z)-ll,13-tetradecadienal, (Z )-ll-tetradecenyl acetate and (Z )-ll,13-tetradecadienyl acetate in the ratio of 1 4 10 40. Best results for trapping were obtained with mixtures of (Z )-ll-tetradecenal and (Z )-ll,13-tetradecadienal in the ratio of 1 4 to 1 9. ... 

Fig. 4.7. Volatiles identified from the bolas spider Mastophora cornigera and Mastophora hutchinsoni (15-19) and the pheromone components of Tetano-lita myenesalis (20, 21). 15, (Z)-9-Tetradecenal 16, (Z)-9-tetradecenyl acetate 17, (Z)-ll-hexadecenal 18, (Z)-ll-hexadecenyl acetate 19, (9Z,12F)-9,12-tetradecadienyl acetate 20, (3Z,6Z,9Z)-3,6,9-henicosatriene 21, (3Z,9Z)-(6S, 1R) ...

Another example of pheromone diversification occurs in the larch budmoth, Zeiraphera diniana, complex. The two species use ( )-9- and (E)- 1-tetradecenyl acetates as a pheromone, the larch-feeding type in a 100 1 ratio and the pine-feeding... 

Fig. 8.2. Geographic variation in male attraction to pheromone in the turnip moth, Agrotis segetum as percentage capture at 11 localities in Eurasia and Africa. The numbers above each column indicate the highest catch of the best lure. Z5, (Z)-5-decenyl acetate Z7, (Z)-7-dodecenyl acetate and Z9, (Z)-9-tetradecenyl acetate. Within each diagram, differing letters indicated = 0.05. (FromToth et al, 1992.)...

A second example of geographically based differentiation is seen in the New Zealand torticid Planotortrix exessana (Foster el al., 1989). This species employs a mix of (Z)-5- and (Z)-7-tetradecenyl acetates. Initially, it was thought that there were two discrete, geographically based groups of females (Foster el al., 1986), one with... 

A second and perhaps more common possibility is suggested by the occasional attraction of male moths to compounds very closely related to actual constituents of a pheromone. For example, in wind tunnel trials, about 5% of the males of the strain of the European com borer (O. nubilalis) that uses (Z)- and ( )-l 1-tetradecenyl acetate in a 97 3 ratio are attracted to a 2 1 mix of (Z)- and ( )-12-tetradecenyl acetates, which is the mix of the Asian com borer, Ostrinia furnacalis (Roelofs et al, 2002). Such occasional mistakes also are found in many species when the attractancy of pheromone analogs are evaluated in the field small proportions of males are attracted to the wrong lures. The presumption is that there is a heritable basis for such deviance in at least some of these males. Again, these compounds could be recognized by forgiving receptors (Vickers et al., 1991 Baker,... 

An alternative, plausible scenario for the switch from 11- to A12-tetradecenyl acetates in O. furnacalis that cannot be excluded is a stepwise change. First, 12-tetradecenyl acetates would be added to the An-tetradecenyl acetates, followed by the elimination of the 1 -(etradecenyl acetates. The initial addition of the l2-componenis and the subsequent loss of the An-components could have been favored by either communication interference or reinforcement (sensu Butlin) in contact with other Ostrinia spp. using the ancestral An-components. 

Evidence from field experiments with many moth species, including cases cited above, shows that addition of very small amounts of pheromone components from a closely related species can abolish the attractiveness of a pheromone. For example, addition of as little as 1% (Z)-l 1-tetradecenyl acetate to the synthetic pheromone of the ermine moth Y. rorellus greatly reduces its attractiveness (Lofstedt et al, 1990,... 

Resistance to a mating disruptant composed of (Z)-l 1-tetradecenyl acetate in the smaller tea tortrix, Adoxophyes honmai (Yasuda) (Fepidoptera Tortricidae). Applied Entomology and Zoology 37 299-304. 

Zhao, C., Lofstedt, C. and Xuying, W. (1990). Sex pheromone biosynthesis in the Asian corn borer Ostrinia furnacalis (II) Biosynthesis of ( > and (Z)-12-tetradecenyl acetate involves delta-14 desaturation. Archives of Insect Biochemistry and Physiology 15 57-65. 

Insects make unsaturated as well as saturated hydrocarbons. The former as well as long-chain alcohols and their esters often form the volatile pheromones with which insects communicate. Thus, the female pink bollworm attracts a male with a sex pheromone consisting of a mixture of the cis,cis and cis,trans isomers of 7,11-hexadecadienyl acetate,13 and European corn borer males are attracted across the cornfields of Iowa by czs-ll-tetradecenyl acetate.14 Addition of a little of the trans isomer makes the latter sex attractant much more powerful. Since more than one species uses the same attractant, it is possible that the males can distinguish between different ratios of isomers or of mixtures of closely related substances. 

Insects communicate through the use of a great variety of volatile pheromones. As mentioned in Chapter 8, Section A,l, some moths utilize acetate esters of various isomers of A7 and A11 unsaturated C14 fatty acids as sex pheromones. Some other moths convert the trans-l 1 -tetradecenyl acetate into the corresponding C14 aldehyde or alcohol, while others use similar compounds of shorter (Cn - C12) chain length.143 Some ants use ketones, such as 4-methyl-3-heptanone, as well as various isoprenoid compounds and pyrazines as volatile signaling compounds.144 Other insects also utilize isoprenoids,145 alkaloids,146 and aromatic substances as pheromones. 

Z)-9-tetradecenyl acetate [16725-534] CH3(CH2)3CH=CH(CH2)8OOCCH3 southern armyworm, Spodoptera eridania (with (Z)-9,(E)-12-tetradecadienyl acetate) beet armyworm, Spodoptera exigua... 

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