Pheromones for insects

Peter Witzgall. Pheromones for Insect Control in Orchards and Vineyards, lOBC wprs. Bulletin 2001, VoL 24(2), pp. 114-122. 

The nomenclature of esters is relatively simple, because it is similar to the nomenclature of salts. For instance, the ester obtained from methanol and ethanoic acid (acetic acid) is called methyl ethanoate (methyl acetate). Esters are compounds that comprise a large number of structures depending on what the alcohol and acid components are. Esters with a small molecular mass are volatile substances, in most cases with a pleasant odor. For instance, butyl acetate is responsible for the odor of apples. In nature, some esters serve as pheromones for insects, for example isoamyl acetate which attracts butterflies. Other kinds of esters can be large molecules as for instanee waxes and fats where both the alcohol and the acid components can be long-ehained or eomplicated structures. These natural esters will be diseussed in the ehapter on lipids. In industry, esters are used in the fabrication of polymeric fibers for textile materials and plastic materials for various uses. The most common material is polyethylene terephthalate (PET), the ester prepared from terephthalic acid and ethylene glycol. 

Look up the use of pheromones for insect control. To what general class of biological materials do pheromones belong Are pheromones regarded as toxic to insects In what sense is their use to control insects a green technology ... 

Siddall s chapter in the ARI Proceedings is entitled Commercial Production of Insect Pheromones Problems and Prospects . This paper argues that industry in the USA is deterred from developing pheromones for insect control mainly because of the unrealistic and uncertain requirements of EPA — the very agency charged with the development of alternatives to hard pesticides. The participants in the ARI meeting resolved to request EPA to establish firm, realistic guidelines within one year. Siddall s chapter contains a number of recommendations that could form the basis for reasonable policy decisions. 

Hedin, P. a., R. C. Gueldner, and A. C. Thompson Utilization of the boll weevil pheromone for insect control. In M. Beroza, Ed., Pest Management with Insect Sex Attractants and other behavior-controlling chemicals. ACS Symposium Series N. 23. American Chemical Society, Washington, D. C. 1976. 

This is the first example of a reaction for which the presence of a chelating ligand was observed to facilitate rather than retard metal-catalysed epoxidation (Gao et al., 1987). It was found that the use of molecular sieves greatly improves this process by removing minute amounts of water present in the reaction medium. Water was found to deactivate the catalyst. All these developments led to an improved catalytic version that allows a five-fold increased substrate concentration relative to the stoichiometric method. Sensitive water-soluble, optically active glycidols can be prepared in an efficient manner by an in situ derivatisation. This epoxidation method appears to be competitive with enzyme-catalysed processes and was applied in 1981 for the commercial production of the gypsy moth pheromone, (-1-) disparlure, used for insect control (Eqn. (25)). 

The variation of the chemical structures in both Type I and Type II compounds results from differences in both biosynthetic enzyme systems and their starting material. This topic, however, has been judiciously described in the chapter by R. Jurenka. While the grouping employed in this chapter is based on biosynthetic origin, some chemicals were involuntarily classified considering their functional groups more sizably than the origin. Incidentally, taxonomic information is important for insect pheromone research. In this chapter, the family name (with the common suffix -idae) is associated with the species name. For those species whose family name is not listed in Figs. 1 and 2, the superfamily name (with the common suffix -oidea) is associated. The subfamily name (with the common suffix -inae) is also described for the species in Tor-tricidae, Pyralidae, and Noctuidae. 

All of the suborder Symphyta and many species in the superfamily Aculeata in the suborder Apocrita are solitary insects. Although not requiring the complex semiochemistry of parasitic or social insects, solitary insects employ pheromones for mating, territorial marking, and host marking. Unfortunately, very few of these have been chemically identified. The pheromones of sawflies and seed wasps were extensively reviewed in 1999 [ 14]. The semiochemicals recently identified in solitary hymenoptera, discussed below, are summarized in Table 2 and Fig. 1. 

The sex pheromone communication system basically involves the release of specific chemicals from a pheromone producer (emitter), the transmission of these chemicals in the environment to a receiver, and the processing of these signals to mediate appropriate behavioral responses in the receiver. The chemicals transmitted downwind have been the most obvious targets for characterization. The code was first broken with the publication in 1959 (3) of the sex pheromone for the domesticated silkworm Bombyx mori after extraction of a half million female silkworm pheromone glands and 30 years of classical chemical analyses. The pheromone was found to be (E10, Z12)-hexadecadien-l-ol, which was called bombykol. This work showed that there was nothing magical about the communication system, and chemists around the world were "attracted" to this area of research on insect pheromones. 

Kaissling KE, Thorson J (1980) In Sattelle DB, Hall LM, Hildebrand JG (eds) Receptors for transmitters, hormones and pheromones in insects. Elsevier/North-Holland, Amsterdam, p 261... 

Reproductive pheromones are powerful isolating agents between species, as is well known for insects such as moths and drosophilas (Wyatt, 2003). 

Throughout history, mankind has always been interested in naturally occurring compounds from prebiotic, microbial, plants and animals sources. Various extracts of flowers, plants and insects have been used for isolating compounds whose task, color and odor could be used for various purposes. Many natural products, such as plant hormones, have a regulatory role, while others function as chemical defense against pests. The role of certain compounds is to act as chemical messengers, such as sex-attractants (pheromones) in insects, terrestrial and marine animals and humans. What is the origin of natural products ... 

Pheromones, especially insect pheromones, have become common news stories in the popular press and hence are well known to most people. For instance, most elementary schools in the USA now include coverage of pheromones in general science and biology courses. Concomitant with this widespread coverage and inclusion in elementary school curricula is ongoing basic and applied research, which leads to important practical uses and beneficial applications. Since Butenandt s initial report on the pheromone of the silk worm moth, there have been many reviews of pheromones and recent ones are cited here. This review of the chemistry of insect pheromones will cover the isolation and identification of new pheromones and the synthesis of these compounds as well as other recently reported syntheses of important pheromones. 

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