Pheromone of ant

The third class of stereoisomers is diastereomers. One class of diastereomers arises from the disposition of equivalent groups on carbon-carbon double bonds. If the two groups are on the same side of the double bond, we refer to the isomer as cis if they are on opposite sides, we refer to the isomer as trans. These diastereomers have different physical, chemical, and, frequently, biological properties. Examples that we have seen include the female silkworm moth sex attractant (bombykol), the sex attractants of the brown algae, and the trail pheromones of ants. 

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 ). 

C oH,gO, Mr 154.25, [a] +38.8° (CH2CI2). An alarm pheromone of ants of the genus Manica. The corresponding methyl ketone normanicone (CsHuO, Mr 140.23) and the 4,6-dimethyl-4-nonene homomani-cone (C,H2oO, Mr 168.28) have also been identified, see also ants. 

Parry, K., and E.D. Morgan Pheromones of Ants A Review. Physiol. Entomol. 

Alkanes and alkenes containing about 30 C-atoms are constituents of plant cuti-cular waxes and the surface lipids of microorganisms and animals (D 3.2.4). These waxes play an important role in the hardiness and in the water economy of plants (E 2.2, E 5.4). Undecane, CH3(CH2)9CH3 tridecane, CH3(CH2)nCH3 and pentadecane, CH3(CH2)i3CH3 are alarm pheromones of ants. 7,8-Epoxy-2-methyl-octadecane is a sex pheromone of Lymantria dispar. In brown algae... 

Alkane derivatives Undecane, tridecane, pentadecane (D 3.2.2) Alarm pheromone of ants (Formica sp.)... 

The alarm pheromones of ants are often simple readily available ketones. Syntheses of some of the less trivial pheromones are described below. 

Banno, K., and T. Mukaiyama Stereoselective synthesis of optically-active manico-nes alarm pheromone of ant. Chem. Lett. 1976, 279—282. 

The Barton-Zard pyrrole synthesis has now been extensively applied to synthesis of naniral and unnaniral products containing pyrrole units Methyl 4-methylpyrrole-3-carboxylate is the trail-maker pheromone of the Texas leaf-aitting ant Arm lexaiia It is readily prepared by the Barton Zard method in 60% yield fEq 10 33 ... 

The reductive cleavage of the alkylcobalamine is facilitated by light irradiation and can then proceed at a much more positive potential. A demonstration photoelec-trochemical reactor for the Bij-catalyzed photoelectrochemical synthesis of Michael adduct 17, the alarm pheromone of the ant atta texana (Scheme 9) has been constructed where the complete device is driven solely by solar energy . Hopefully, mediated photoelectrochemical reactions of this type will also be realized at chemically modified electrodes. 

An alternative strategy for (1) would have been to reconnect both substituents into a ring to ensure their ais arrangement. This strategy was used in syntheses of the antibiotic methylenomycin (4) and the trail pheromone of pharaoh s ant, faranal (5). 

Mori reported an improved synthesis of (3S,4P,6 ,10Z)-faranal (37), the trail pheromone of the Pharaoh s ant (Monomorium pharaonis) [84]. As summarized in Scheme 55, the key-reaction was the coupling of iododiene A with iodide E. The geometrically pure A was prepared by the zirconocene-mediated carbo-alumination reaction, and E was prepared from B by the asymmetric cleavage of its epoxy ring to give C (77% ee), which could be purified via its crystalline 3,5-dinitrobenzoate D. 

Although not studied extensively, males of social hymenoptera certainly produce pheromones. Male ants produce aggregation pheromones that attract both sexes to mating areas [6] as well as cause virgin alates to disperse from their colony [ 6 ]. However, these have not been chemically elucidated. 

Glancey BM (1986) The queen recognition pheromone of Solenopsis invicta. In Lofgren CS, Vander Meer RK (eds) Fire ants and leaf-cutting ants biology and management. Westview Press, Boulder, p 223... 

Probably the best-studied communication behavior in ants is chemical communication, but other sensory modalities, such as mechanical cues, also play an important role in the formation of multicomponent signals in ant communication. Chemical releasers are produced in a variety of exocrine glands, and considerable progress has been made in chemically identifying many of these glandular secretions (for reviews see refs. 1 and 2). In this essay I will not emphasize, however, the natural product chemistry of ant pheromones, but rather concentrate on the proposition that communication in ant societies is often based on multicomponent signals, on nested levels of variation in chemical and other cues, which feature both anonymous and specific characteristics (3). 

The female produced sex pheromone of Aleochara curtula has been described to consist of a mixture of (Z)-7-henicosene and (Z)-7-tricosene [114]. The same compounds are reported to be used by young males as a kind of camouflage to avoid aggression from older males. Similarly, chemical camouflage by using hydrocarbons plays a role in the relations between the myrme-cophilous staphylinid beetle Zyras cones and the ant Lasius fuliginosus. The host worker ants never attack these beetles which show the same profiles of cuticular hydrocarbons as the ants [115]. 

Thirdly let ns consider ants. They are a social gronp and may forage across snbstantial distances as a group. Ants lay down a molecnlar trail for other ants to follow. The molecnles involved are termed trail pheromones. Now there are many species of ants and they nse different trail pheromones for the obvions reason of being able to follow the right trail as opposed to that of some other species. That for the hre ant, Solenopsis invicta, is a hydrocarbon of moderate complexity ... 

So far in our discussion, life has been simple in one respect each action of a pheromone has been the consequence of one or two, or a few in the case of the brown algae, molecules in one species. In nature, things can be more complex. One molecule can serve as a pheromone for multiple species benzaldehyde serves as a trail pheromone for bees, Trigona genus a defense pheromone for ants, Veromessor genus and as a male sex pheromone in the moth, Pseudaletia genus. 

The highly organized, emergent social behavior of ants reflects the action of a number of ant pheromones. 

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