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Figure 3.37 Defensive secretion macrocyclic lactones of Amitermes termites. Note the odd number of carbon atoms in two compounds

Figure 3.37 Defensive secretion macrocyclic lactones of Amitermes termites. Note the odd number of carbon atoms in two compounds

Figure 3.38 Macrocyclic lactones from beetle aggregation pheromones. Compound A is found in Cryptolestes pusillus, the flat grain beetle, compounds B and E in C. surinamensis, a mixture of enantiomers of C in C. turcicus, compound D and the R-enantiomer of E in C. ferrugineus, the rusty grain beetle

24-tetracosanolide have all been identified along with the a-hydroxy- and p-hydroxytetracosanolides shown in Figure 3.37.

Males of some stored grain beetles use macrolides for aggregation pheromones, making them from fatty acids by oxidation at the terminal or next-to-terminal carbon atom (Figure 3.38).

The Argentine ant Linepithema humile which has invaded Australia and Mediterranean Europe produces a macrolide evidently made from a fatty acid where synthesis begins with 2-methylbutyric acid (Figure 3.39). The Dufour glands of halictine and colletine bees frequently contain mixtures containing macrocyclic lactones. Colletes bees, for example,

13-(1 -methylpropyl)-tridecanolide

Linepithema humile

18-octadecanolide

20-eicosanolide

I O 18-octadec-9-enolide

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