Argentine ant

Akita and Ohta disclosed one of the earliest Sonogashira reactions of chloropyrazines and their A-oxides [24, 25]. The union of 2-chloro-3,6-dimethylpyrazine (23) and phenylacetylene led to 2,5-dimethyl-3-phenylethynylpyrazine (29). Subsequent Lindlar reduction of adduct 29 then delivered (Z)-2,5-dimethyl-3-styrylpyrazine (30), a natural product isolated from mandibular gland secretion of the Argentine ants, Iridomyrmex humilis. 

Chart 8.1.1 Isoprenoids (skeletons) widespread on land (5max=45, av=29 S/Hm x-0.60, av=0.47). Monoterp. men thane (Compositae, Ang. from temeperateand subtropical, not forested, areas and Bryoph. AY) thujane (Ang. AY) bomane camphor and bomeol (tropical and subtropical Lauraceae and Mediterranean Labiatae, Ang. AY) pinane (Ang. and Gymn. MI AY) iridoids (Ang. and Argentine ant, Iridomyrmex humilis Mayr., Ins. BR MI). 

Antimicrobial, insecticide/insectivorous animals isopr. (iridoid mwioterp.)/ iridomyrmecin r Argentine ant, Irichmyrmex huittilis Mayr., Ins. MI... 

Markin, G. P. (1970). Food distribution within laboratory colonies of argentine ant, Iridomyrmex humilis (Mayr). Insectes Sociaux 17 127-158. 

Liang D. and Silverman J. (2000) You are what you eat diet modifies cuticular hydrocarbons and nestmate recognition in the Argentine ant, Linepithema humile. Naturwissenschaften 87, 412-416. 

Torres, C. W., Brandt, M. and Tsutsui, N.D. (2007). The role of cuticular hydrocarbons as chemical cues for nestmate recognition in the invasive Argentine ant (Linepithema humile). Insect Soc., 54, 363-373. 

Vasquez, G.M., Schal, C. and Silverman, J. (2008). Cuticular hydrocarbons as queen adoption cues in the invasive Argentine ant../. Exp. Biol., 211,1249-1256. 

The structure for valerosidate is incorrect in the previous Report (Vol. 5, p. 17). A new valepotriate has been isolated from Valeriana officinalis and shown spectroscopically to be 7-epideacetylisovaltrate (103) 193 it is also shown to be related to didrovaltrate (104) stereochemically, but in view of the recently reported absolute configuration of didrovaltrate (104)192 this assignment must be questioned. The occurrence of iridoids in the Argentine ant Iridomyrmex humilis has been re-investigated.194... 

Trail pheromones of ants offer many opportunities for experimentation. For example, the Argentine ant s trail pheromone is (Z)-9-hexadecanal. Trail following can be disturbed by an overdose of pheromone. The investigators (Snckling et al. 2008) used the pheromone on wax-coated sand (1 g sand, 0.2 g wax, 25 mg pheromone per m ). 

Suckling DM, Peck RW, Manning LM, Stringer LD, Cappadonna J, El-Sayed AM (2008) Pheromone disruption of argentine ant trail integrity. J Chem Ecol 34 1602-1609 Travis H (2003) Pheromone caterpillar trails An easy lab exercise for the classroom. Am Biol Teacher 65 456-461... 

Van Vorhis Key, S.E. T.C. Baker. 1982. Specificity of laboratory trail following by the Argentine ant, Iridomyrmex humilis (Mayr), to Z-9-hexadecenal, analogs, and gaster extracts. J. Chem. Ecol. 8 1057-1063. 

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 coUetine bees frequently contain mixtures containing macrocyclic lactones. Colletes bees, for example. 

In 1949 Pavan isolated the substance he called iridomyrmecin from the Argentine ant Iridomyrmex humilis (now Linepithema humile). Iridomyrmecin, dolichodial and other monoterpenes with a methylcyclopen-tanoid structure are called iridoids (Figure 6.12). They act as defensive compounds in ants, stick insects, rove beetles and leaf beetle larvae. Some of the group (e.g. the isomer of nepetalactone shown in Figure 6.12) are also sex pheromones in aphids. Reaction of iridomyrmecin with... 

This lactone, which comprises about 1 % of the body weight of the Argentine ant, may be isolated by petroleum ether extraction or steam distillation. For a review of the literature on the isolation and structure determination of iridomyrmecin (I) and the related substances isoiridomyrmecin (II), iridodial (III) and dolichidial (IV), found in ants of the same genus, see Cavill (i960). 

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