Insect pheromones

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500,000 odor glands of the female silk moth ( Bombyx mori ) were needed to elucidate the molecular structure of the bombykol.
Structural formula of bombykol , the first clearly chemically identified insect pheromone

Insect pheromones are chemical messengers that the chemical communication between individuals of insects - kind serve. In this way they differ from kairomones , i.e. messenger substances that transmit information to alien organisms. Insects produce pheromones in special glands and release them into the environment. In the pheromone receptors of the recipient's sensory cells, even in very low concentrations, they generate a nerve stimulus that ultimately leads to a behavioral response . The intra-species communication of the insects via these substances takes place in a variety of ways and is used, among other things, to find sexual partners , to maintain harmony in a colony of socially living insects , to mark territories or to find nesting places and food sources.

In 1959, the German biochemist and Nobel Prize winner Adolf Butenandt identified and synthesized the unsaturated fatty alcohol bombykol , the sex pheromone of the silk moth ( Bombyx mori ), as the first known insect pheromone. The sex pheromones of female butterflies are mostly mono- or bis- olefinic fatty acids or their esters , fatty alcohols, their esters or the corresponding aldehydes . Male moths use a wide range of chemicals as sex pheromones, including pyrrolizidine alkaloids , terpenes, and aromatic compounds such as benzaldehyde .

Research into the chemical communication of insects broadens our understanding of how they find their sources of food or places to lay eggs. Beekeepers use an artificially produced Nasanov pheromone that contains terpenes such as geraniol and citral to lure bees to an unused beehive . The agricultural and forestry uses commercially insect pheromones in pest control by insect trap for the prevention of egg laying and in the practice of the disrupter . It is expected that in this way insect pheromones can also help to contain insect-borne infectious diseases such as malaria , dengue fever or African trypanosomiasis .

Etymology and classification

In 1959, Adolf Butenandt and Peter Karlson proposed the term pheromones for substances that serve intraspecific communication. The definition of the term pheromone was made in the same year by Karlson and the Swiss zoologist Martin Lüscher . So are pheromones

“ Substances that are released from one individual to the outside and trigger specific reactions in another individual of the same species. "

- Peter Karlson, Martin Lüscher, 1959.

The word pheromone consists of the ancient Greek parts φέρειν phérein, convey, report and ὁρμᾶν hormān, drive, excite. According to Karlson and Lüscher, the aim was to create an internationally understandable scientific term for a class of substances based on a clear definition. It should be a short word that can be spoken in many languages. The ending mon served as a suffix , as it occurs in the words Hormon , Kairomon and Allomon and thus underlined their relationship. The term pheromone replaced the term ectohormone or homoiohormone , which Albrecht Bethe had already proposed in 1932 with the same definition. The term Bethe did not catch on because the terms ecto and hormone were mutually exclusive, according to Butenandt. The mechanism of action of a pheromone also does not correspond to that of a hormone absorbed into the bloodstream by another individual and was therefore perceived as misleading.

The classification of the intraspecificly acting pheromones in the group of semiochemicals , i.e. the messenger substances that facilitate communication between organisms, is shown in the following graphic:

Semiochemicals1.svg

According to the type of reception, Karlson further subdivided them into olfactory and oral insect pheromones. In 1963, Edward O. Wilson , who had discovered the trace pheromones of ants the year before , and William H. Bossert introduced the terms releaser and primer pheromones. Releaser pheromones, which are mostly perceived olfactory, cause an instantly observable behavioral reaction, whereas primer pheromones, which often have an oral effect, trigger physiological changes in the recipient. Primer pheromones, for example, suppress the formation of the ovaries in worker bees .

Often, pheromones are defined according to their behavior-triggering function. In addition to the well-known sex attractants, they also act as aggregation pheromones , dispersion pheromones, alarm pheromones, track pheromones, marker pheromones, brood recognition pheromones, egg laying pheromones, recruiting pheromones or as box recognition substances.

Vincent Dethier divided the insect pheromones into six categories according to their general behavioral effect. These include the arrestants, which are normally only perceptible from a short distance , which cause an insect in motion to stop, as well as the locomotor stimulants, which increase the speed of the insect or reduce the number of changes in direction. Attractants are attractants that trigger an oriented movement towards the odor source, whereas repellents trigger an escape movement away from it. Feeding or oviposition stimulants trigger feeding or oviposition. Deterrents, on the other hand, inhibit eating or laying eggs.

Functionally defined insect pheromones often contain mixtures of different components in precisely defined proportions. These so-called pheromone cocktails often contain substances of various categories with a near and far orientation function. The aggregation pheromone cocktail of the German cockroach Blattella germanica contains both substances that act as an attractant and substances that act as an arrestant .

In some cases, insect pheromones are named after their place of biological production. Males of different types of butterfly, such as the banana butterfly, have so-called androconial organs in their abdomen that release pheromones. These insect pheromones are appropriately referred to as androconial pheromones. The queens of the western honey bee produce the queen bee pheromone in the mandible glands . In the English-speaking world, they are therefore often referred to as Queen Mandibular Gland Pheromones, queen mandibular gland pheromones .

history

First discoveries

John Ray

The English beekeeper Charles Butler observed in 1609 that a liquid was released when a bee stung. This liquid attracted other bees and they began to sting en masse. For the first time, Butler demonstrated the action of a bee alarm pheromone, which was identified as isoamyl acetate in the 1960s .

Sir John Ray suspected as early as 1690 that female birch moths attracted male conspecifics with a scent:

“It emerged out of a stick-shaped geometer caterpillar: it was a female and came out from its chrysalis shut up in my cage: the windows were open in the room or closet where it was kept, and two male moths flying round were caught by my wife who by a lucky chance were into the room in the night: they were attracted, as it seems to me, by the scent of the female and came in from outside. "

"It developed from a rod-shaped moth caterpillar: it was a female and came out of her pupa that was locked in my cage: the windows were open in the room or chamber where she was kept, and two male moths that were flying around, were caught by my wife, who was in the room that night by a happy coincidence: They were, it seems to me, attracted by the female's scent and came in from outside. "

- John Ray
Jean-Henri Fabre

The French entomologist Jean-Henri Fabre also reported in the middle of the 19th century on experiments with night peacock moths and oak spiders , in which females caught in wire cages attracted hundreds of males within a few days at certain times of the day. In experiments with marked silk spider males, 40% of the males found a captured female from a distance of four kilometers and 26% of the males from eleven kilometers.

In the case of many insect species, researchers puzzled for a long time about the mechanism by which the sexual partners found each other: visual or acoustic stimuli could neither explain the experiments carried out by Fabre nor how moths found females ready to mate with great certainty. Theories about attraction by infrared or other radiation were not confirmed. The organization of insect states remained just as inexplicable for a long time . The writer and bee researcher Maurice Maeterlinck speculated on the spirit of the hive, the (team) spirit of the beehive , without being able to determine its essence.

Bethe Definitions of Bethe

At the beginning of the 20th century discovered Ernest Starling , the hormones as the first biological messengers. In 1932 the neurophysiologist Albrecht Bethe , who at that time was head of the Institute for Animal Physiology at the University of Frankfurt am Main , published an article about an extended hormone concept in which he differentiated between endohormones and ectohormones . The endohormones therefore work in the producing organism itself and correspond to the classic hormone definition. In contrast, the organism releases ectohormones to the outside and transfers them to other individuals. As an example, Bethe cited the effects of the lactation hormone given by a fetus to the mother, causing the mammary gland to grow and then to produce milk . He proposed this concept for chemical communication among insects as well.

“With the bees z. For example, the workers (not the mothers) are able to raise a sexually capable queen from an egg or a young larva [...] through special food and the transfer of secretions from their salivary glands. There can hardly be any doubt (although it has not been proven) that ectohormones of the salivary gland secretion play the main role in this re-differentiation. "

- Albrecht Bethe

Bethe further subdivided the ectohormones into homoiohormones, which - according to the current definition of a pheromone - act on individuals of the same species, and alloiohormones, which act on individuals of a different species. In doing so, he coined the precursor term for allelochemicals .

Works by Butenandt

Adolf Butenandt also suspected that communication among insects was based on messenger substances, and in the 1940s began a project to identify the sex attractant of the silk moth ( Bombyx mori ). It is a butterfly from the family of the real spinner , originally native to China , which is used for silk construction and whose rearing and keeping were well known. It was only after almost 20 years of work that the final extraction and purification of a substance from more than 500,000 insects, which Butenandt later called Bombykol , was successful .

Butenandt determined the molecular formula of the substance by elemental analysis to be C 16 H 30 O. Infrared spectroscopic investigations indicated the presence of conjugated double bonds . Using methods common at the time, such as catalytic hydrogenation , determining the melting point and oxidative degradation by potassium permanganate , Butenandt showed that the substance in question was an unsaturated fatty alcohol , (10 E, 12 Z ) -10,12-hexadecadien-1-ol , acted.

Butenandt then synthesized bombycol from vernolic acid [(12 R , 13 S ) -epoxy-9- cis -octadecenoic acid] in several steps via diol formation, its cleavage into the aldehyde , double bond isomerization and Wittig olefination . He synthesized the four possible stereoisomers and tested them for their biological activity . Only one isomer showed the same activity as the extract. Butenandt thus provided evidence that communication among insects takes place on a material basis.

"However, through extraction and condensation experiments it has been shown convincingly that there must be a material principle that is secreted by the female butterflies from the olfactory organs of the last abdominal segments and perceived by the males with their antennae."

- Adolf Butenandt

Primer and releaser pheromones

EO Wilson

Towards the end of the 1950s, Edward O. Wilson defined substances that trigger the alarm and burrowing behavior of ants as chemical releasers. In 1961, the British biochemist Robert Kenneth Callow identified the compound ( E ) -9-oxo-dec-2-enoic acid , or 9-ODA for short , another pheromone, also known as the queen bee pheromone. The effect of this pheromone was obviously different from that of the alarm pheromones, as it had a long-term effect on the physiology of the recipient.

In 1963, Wilson, who had discovered the trace pheromones of ants the year before, and William H. Bossert introduced the term releaser and primer pheromones to describe the behavior-regulating effect of, for example, sex pheromones from the pheromones that are in the hormone system of the Intervene to distinguish.

Modern research directions

Through the extraction and analysis processes , which have been enormously refined over the years , chemists and biologists have identified numerous other pheromones. For the detection of the second component of the pheromone cocktails of Bombyx mori, the Bombykals [(10 Z, 12 E ) -Hexadecadienal] was enough in 1978 already an extract of 460 glands, of which 15  nanograms of the aldehyde was isolated.

Preparation from Helicoverpa zea

In addition to researching the function and reception of pheromones and chemical identification, scientists extensively studied the biochemistry of pheromone production. In 1984 Ashok Raina and Jerome Klun discovered that the production of the female sexual attractant of the owl butterfly Helicoverpa zea is controlled by hormonal substances, the so-called pheromone biosynthesis-activating neuropeptides (PBAN) in the brain of female moths. Other modern research focuses are the investigation of the reception of insect pheromones by means of the olfactory and taste senses, genetic factors and evolutionary biological issues such as the coevolution of female sex pheromone production and reception in males.

The fight against disease vectors such as the malaria mosquito is another focus of research. According to estimates by the World Health Organization , the number of malaria infections in 2012 was around 207 million with 627,000 deaths. Culex mosquitoes transmit the pathogen causing filariasis or the West Nile virus . One way to contain these populations is to use traps equipped with egg-laying pheromones. In order to optimize this, the odor-binding proteins in the antennae of the females, which play a decisive role in recognizing the egg-laying sites, are intensively examined.

Manufacturing

The secondary products of fatty acids , such as saturated and unsaturated hydrocarbons , fatty alcohols, esters and aldehydes, but also isoprenoids and other compounds , often serve as pheromones in insects . Pheromones are often not pure substances, but so-called pheromone cocktails, which consist of various components. Often only one particular enantiomer of a compound triggers a behavioral reaction, while the other enantiomer does not trigger any or a different reaction.

Sometimes the biosynthesis of the pheromone only takes place when the biochemical precursors have been absorbed from food plants in the form of certain alkaloids . In this case, the sexual attractant also signals the presence of food sources.

Due to the potential commercial application in crop protection , the intensity of the investigation of pheromones increased sharply after Butenandt's discovery and led to the development of highly sensitive analytical methods and the broad application of chemo- , regio- and stereoselective syntheses in organic chemistry.

biosynthesis

Male of the imperial coat with four elongated scented flakes (scented flakes) on each forewing

Insect pheromones are made by a large number of exocrine glands , which consist primarily of modified epidermal cells at various points on the insect's body. In addition to the sexual attractant bombykol, the abdomen glands of the silkworm female give off traces of the ( E , E ) isomer of alcohol as well as the analogous ( E , Z ) -aldehyde bombykal. Suitable surface geometries in the vicinity of the glands, such as grooved pore plates, can promote the effective evaporation of a leaked pheromone. Honey bees have 15  glands with which they produce and release a number of different substances and thus maintain a complex communication system based on pheromones . Males of different butterfly species have so-called androconial organs in their abdomen with which they can spread pheromones, other butterflies release these via scented scales or scented bristles on their front wings or the end of the abdomen. The scented bristles and scented scales serve to enlarge the surface and facilitate the evaporation of the insect pheromones.

Instead of developing a completely unique series of enzymes for pheromone biosynthesis, insects often modify normal metabolic products to pheromones with high regio-, chemo-, ( E / Z ) -, diastereo- or enantioselectivity and in precisely defined proportions. The biosynthesis of the insect pheromones takes place either de novo according to the scheme of fatty acid synthesis through successive cultivation of malonyl-CoA on an initial acetyl or through the ingestion of precursors from food. Many butterflies use the biosynthetic possibility of producing a certain mixture of derivatives of simple fatty acids. The development of the enzyme Δ-11- desaturase in combination with chain-shortening reactions allows them to produce a variety of unsaturated acetates , aldehydes and alcohols in various combinations.

Special enzyme systems may dehydrate the carbon chain and reduce the acid function to alcohol. Further steps can be the oxidation to the aldehyde or the acetylation to the acetic acid ester . In Bombyx mori , the biosynthesis of pheromones is activated every day by a neurohormone , the so-called pheromone biosynthesis-activating neuropeptide (PBAN).

The hormonal mechanisms of pheromone production differ significantly from species to species. Juvenile hormones, for example, control the pheromone production of the owl butterfly Mythimna unipuncta . These are formed in the corpora allata , usually in pairs, located behind the brain and released into the hemolymph . There they bind to certain transport proteins. When the corpora allata is removed, the females do not produce pheromones. Juvenile hormones, however, have an indirect effect on the circadian release of PBAN.

Pheromones made from plant ingredients

Retronecine from which many PAs by esterification of the hydroxy groups descended

Male fire beetles of the species Neopyrochroa flabellata and various other beetle species use the terpenoid cantharidin as a sex pheromone or aphrodisiac capheromone. This isoprenoid is ingested by Neopyrochroa flabellata with food and transferred to the females during the mating act and then to the brood. The females check the content of a gland on the head of the male before mating. The cantharidin acts as a food poison and makes the eggs inedible for predators; Females therefore prefer males with a high cantharidin content.

In the larval stage, moths such as Utetheisa ornatrix and Tirumala limniace ingest pyrrolizidine alkaloids from food plants such as crotalaria , solstices or yarrow liver balsam , which the adult male converts into pheromones such as hydroxydanaidal through oxidation . As with the fire beetle, the alkaloids, which are strong poisons and act against predators such as spiders , ants or netwings , are transferred to females and eggs. Adult monarch butterflies take up phytochemicals and thus increase their pheromonal attractiveness. Sometimes the biosynthesis of the pheromone only takes place when the biochemical precursors have been absorbed from food plants in the form of certain alkaloids . In this case, the sexual attractant also signals the presence of food sources.

The uptake of pheromone precursors from plants is also known for certain species of jewel bees and bored flies . Male bees collect a mixture of terpenoids from orchids and use them as an aggregation pheromone to form courtship areas . Sometimes the phytonutrients control the development of the pheromone glands of male butterflies.

Laboratory synthesis

Structure of cantharidine

Karl Ziegler and Günther Otto Schenck succeeded in synthesizing cantharidin as early as 1941. The preparation of the pheromones requires the use of highly chemo- , regio- and stereoselective syntheses . In the 1970s, asymmetric synthesis using the SAMP method succeeded in producing various pheromones in enantiomerically pure form. Furthermore, chemists used asymmetric epoxidation , asymmetric dihydroxylation , biocatalysis , olefin metathesis and many other stereoselective reactions to synthesize pheromones. The Wittig reaction is suitable for the synthesis of pheromones with (Z) - olefinic double bonds .

Genetically modified tobacco plants can also produce sex pheromones. The fatty alcohols obtained therefrom by extraction are then acetylated in order to obtain the respective target sex pheromones. This semi-synthetic route of manufacture produces insect pheromones in relatively large quantities and with a high degree of purity.

properties

Glass winged pheromone dispenser

Chemical communication between living beings using pheromones is based on the same principles as technical data transmission . A transmitter , for example the gland of a female insect, emits the signal in the form of a chemical substance . Both the chemical structure of the molecules and their proportions determine the information content and serve as a common repository of symbols for the species. The physical properties of the substances such as the vapor pressure determine the function of their molecules as carriers of short or long distance information.

The insect pheromone is transmitted through direct contact or through a medium such as water or air. The substance is received by the recipient , for example the pheromone receptors in the antenna of a male insect, and triggers a behavioral reaction. The term antenna was first used for the antennae of insects and then in technology. Insect pheromones have a highly species-specific effect, which means that they only cause the desired behavioral reaction in conspecifics , but not in individuals of other species. For example, although the chemical compounds that act as sex pheromones in butterflies may be the same in different species, the composition of the pheromone cocktail is different in all species. In addition, the pheromone cocktails often contain substances that act as behavior inhibitors for other species and, for example, considerably reduce the approach rate of males of foreign species to a luring female.

Physico-chemical properties

The pheromones are mostly produced as a liquid and either transferred through direct contact or released into the environment as a liquid or vapor . They can be of low or high volatility . The ability to diffuse significantly influences the function of the pheromone. Alarm pheromones are often highly volatile in order to spread quickly by diffusion . They are therefore often short-chain substances with a relatively high vapor pressure and low complexity. There are no high demands on the species-specific effect of the coding, as is the case with sex pheromones. Sex pheromones are more complex than most alarm pheromones, but have a lower molar mass than marker pheromones that permanently indicate an area.

In flying insects - such as butterflies - the pheromone as a molecule must not be too large, otherwise the vapor pressure and volatility are too low. Over 200 identified sexual attractants from butterfly species are mono- and bis-olefinic fatty aldehydes , fatty alcohols and their acetates with chains of 10 to 18 carbon atoms.

There are different emission and reception scenarios depending on the function. Ants, for example, emit alarm pheromones intermittently or continuously in the mostly windless environment of the ant den. Trace pheromones are sent out by an ant as a moving source. The silk moth's sex pheromones are expelled in a stream of air in discrete fragrances.

Male monarch butterfly with clearly visible scented pouches

Male monarch butterflies do not emit volatile pheromones, but pheromone-laden nanoparticles , known as pheromone transfer particles, which they use to transfer arrestants or aphrodisiac capheromones to the females. The males position the pheromone transfer particles on their brush hairs and scatter them during the courtship flight. The nanoparticles stick to the females' sensors equipped with pheromone receptors, where they slowly release the pheromones and thus lead to a long-lasting stimulus for the female.

Females of the arctic bear moth species Pyrrharctia isabella emit an aerosol that consists exclusively of droplets of sex pheromones. The amount of pheromone released is much larger than that of other known female butterflies. The apparent waste of the sex pheromone can be explained by the short period of time that an adult animal has to find a reproductive partner due to the short arctic spring.

Most recipients perceive pheromones in an environment that is characterized by the presence of many other chemicals. In order to guarantee a specific perception, the pheromone chemical must either be so complex that it does not occur repeatedly in nature, or the correct ratio of several individual components must trigger the stimulus . However, it has been shown that only in exceptional cases does a single substance convey the message . Often a mixture of substances has to be present in very precise proportions which, in addition to the chemical structure of the individual pheromones, determine the information content of the pheromone cocktail.

Periplanon B

The chemical structure of pheromones is directly related to their signal function and signal environment . Pheromones released into the air often have a carbon chain of 5 to 20 atoms and a molar mass of around 80 to 300  g · mol −1 . With a carbon chain of fewer than five carbon atoms, the number of possible isomers is low and specific species-specific coding is difficult. With longer carbon chains, the number of possible isomers increases rapidly.

Periplanon B , the sex pheromone of the American cockroach , is an example of a complex single substance to which males respond in extremely small quantities of 10 −5 nanograms .

Biological properties

Antenna of a woolly moth

The sex pheromone cocktail released by a female insect spreads downwind. In the recipient male, the molecules hit the antennae, where the pheromones are received by olfactory cells on the olfactory hair or sensillia . The antennas adsorb about 30% of the pheromone molecules contained in an air stream. The other molecules hit the outer body cover and are enzymatically broken down there.

The pheromone molecules first reach the cuticle of the olfactory hair and diffuse through pores into a pore vessel and from there into tubules . From there, the molecules diffuse on to the dendrite membrane . This membrane has receptors which, when a pheromone is received, cause a change in the electrical resistance via the opening of ion channels and generate an electrical potential that triggers a sensory stimulus . A single pheromone molecule can trigger a nerve impulse. The recognition of a special pheromone cocktail, however, requires a certain level of excitation of different cell types with different specificities . It is assumed that the characteristic excitations received from the various receptors in the central nervous system are modulated there to form an excitation pattern . If this excitation pattern , which depends on the quantity ratio of the pheromone molecules received, corresponds to the coding of an innate behavioral pattern , this leads to the triggering of a corresponding behavioral response, such as a headwind approach to a pheromone source.

Pheromone species

According to their effect, two classes of pheromones, the primer and the releaser pheromones, can be distinguished. Under certain conditions, certain pheromones act as both releaser and primer pheromones.

Releaser pheromones

Release pheromones have a brief, direct behavior-controlling effect. The first pheromone discovered, bombykol, is an example of this. In addition to the known sex attractants, the release pheromones typically include aggregation pheromones, dispersion pheromones, alarm pheromones, trace pheromones and marker pheromones.

Aggregation pheromones

Aggregation of stink bugs

Aggregation pheromones are produced by both sexes and serve to gender non-specific attraction of individuals of the same species. These include the bark beetles and other beetles, Diptera , Schnabelkerfen and grasshoppers known. Insects use aggregation pheromones to defend themselves against predators, when choosing a partner and to overcome the resistance of host plants in the event of a mass attack. A group of individuals in a location, regardless of gender, is called an aggregation . In addition to sex pheromones, aggregation pheromones play an important role in the development of pheromone traps for selective pest control.

Investigations using the electroantennogram technique showed that aggregation pheromones triggered relatively high receptor potentials in a gender-unspecific manner, whereas sex pheromones only triggered high receptor potentials in one gender. The aggregation pheromones are therefore possibly evolutionary precursors of the sex pheromones.

Sex pheromones

Copulating poplar hawk couple

Sex pheromones signal the willingness of the female animal to mate . Male animals also emit pheromones; they contain information about gender and genotype . Many insects release sex pheromones; some butterfly species perceive the pheromone at a distance of 10 kilometers. The sensory cell response in the male silk moth begins at a concentration of around 1000 molecules per cubic centimeter of air. As soon as a certain concentration limit is exceeded, the olfactory signal of a female initially triggers an oriented headwind flight in the male silkworm. In other species, such as the codling moth, on the other hand, the male checks the stereochemical purity of the attractant molecule. As soon as there is a small addition of another stereoisomer in the pheromone cocktail, there is no approach to the source. The other stereoisomer acts as a repellent in this case . In addition to the main components, some species also release so-called near-range components in small quantities, which influence behavioral reactions.

Foraging honey bees spread the scent of ( Z ) -11-eicosen-1-ol. Beewolf females use this scent to guide them to prey on honey bees. The male bees use this component and thus the existing sensory preference of the females for the scent of bees as part of their sex pheromone cocktail to attract them.

Aphrodisiac capheromones

Olean - the aphrodisiac capheromone of the olive fruit fly ( Bactrocera oleae )

Aphrodisiacs pheromones stimulate the willingness to mate. The spiroacetal olean, for example, is the aphrodisiac capheromone of the olive fruit fly ( Bactrocera oleae ). Only the ( R ) - enantiomer acts on the manikin ( S ) enantiomer is ineffective with them. The female produces the racemate , responds to ( R ) - and ( S ) -Olean and thus also stimulates herself.

So-called anti-aphrodisiacs have exactly the opposite effect. Nymphs of the bed bug protect themselves with such a pheromone which a certain mixing ratio of the aldehydes ( E ) -2-hexenal , ( E ) -2-octenal and 4-oxo- ( E ) -2-hexenal , against Begattungsversuche bed bug males. This drills a hole directly into the abdomen of sexually mature female bugs and injects its sperm there ( traumatic insemination ). However, such an injury can be fatal for mated nymphs.

Alarm pheromones

Some species of insect emit alarm pheromones when attacked. These trigger either flight or increased aggression. In the case of bees, for example, two alarm pheromone mixtures are known. One is released by the Koschevnikov gland near the sting and contains more than 40 different compounds, such as the isoamyl acetate already described in the effect by Butler , as well as butyl acetate , 1-hexanol , 1-butanol , 1-octanol , hexyl acetate , octyl acetate and 2-nonanol . These components have a low molar mass , are volatile, and are the most unspecific of all pheromones. Alarm pheromones are released when a bee stings another animal in order to attract other bees and induce them to attack. Smoke suppresses the effect of alarm pheromones, which beekeepers take advantage of.

The honeybees' other alarm pheromone mainly contains 2-heptanone , another volatile substance that is released by the jaw glands. This component has a repulsive effect on predatory insects. The bed bug alarm pheromone cocktail contains unsaturated hexene and octene aldehydes, which are perceived as a characteristic, sweet smell in rooms infested with bugs.

Marking and Dispersion Pheromones

Certain insects like the cherry fruit fly mark their egg-laying places in such a way that other females of the same species avoid the place and lay their eggs in other places in order to avoid competition for food among the offspring. Territorial social insects, such as colonies of ants, mark territories claimed by them with pheromones.

The marker pheromones include the dispersion pheromones with which, for example, bark beetles prevent over-colonization of a tree. The females and nymphs of the German cockroach transmit dispersion pheromones in direct contact via their saliva. In the nymph stage, these serve to deter adult cockroaches and thus to protect against cannibalism . In adult animals, they prevent the relocation of a habitat.

Trace pheromones

Fire ants use trace pheromones to mark the route from the colony to feeding grounds.

Trace pheromones are mainly known from insects living in colonies , which mark their paths with non-volatile substances such as high molecular weight hydrocarbons . Ants in particular often mark the path from a food source to the nest in this way. As long as the food source exists, the trail is renewed. When the food source runs dry, the ants spray the trace pheromone with a repellent pheromone. The American naturalist Charles William Beebe reported in 1921 on the phenomenon of the ant mill, which trace pheromones can trigger in wandering ants : If the animals are separated from the main trace of the colony, the blind ants follow the pheromone traces of ants running in front of them. These run in large circles to the point of complete exhaustion or death without finding their way back to the colony.

Recruiting Pheromones

Recruiting pheromones are widely used as an element of chemical communication among social insects and have been shown to be found in bees, termites, and ants. These pheromones are used by insects to encourage other members of the colony to forage from a food source. Bumblebees perform a dance similar to the bee dance, which is primarily used to distribute recruitment pheromones.

Primer pheromones

The hymenoptera is the largest group of eusocial insects, including many bees , especially the subfamily Apinae , ants and some species of wasps , especially the subfamily of the real wasps . The characteristics are often the presence of a reproductive queen and castes with specialized workers . Termites form the second large group of eusocial insects. The colonies are divided into different castes, with a queen and a king as reproductive individuals, workers, and soldiers defending the colony. Primer pheromones have a major influence on the organization of hymenoptera states and termite colonies formed by hymenoptera . These pheromones affect the recipient's hormonal system ; they often intervene in the metabolism via a signal cascade or activate proteins that can bind to the DNA . In contrast to the releaser pheromones, the primer pheromones are less well studied. For a long time, only one primer pheromone, 9-ODA, was known.

Primer pheromones of bees

A well-known example of primer pheromones are the queen bee pheromones. These pheromones control the social behavior, the maintenance of the honeycombs, the swarming and the formation of the ovaries of the worker bees. The components are carboxylic acids and aromatic compounds . For example, ( E ) -9-Oxo-dec-2-enoic acid (9-ODA) suppresses the further breeding of queens and inhibits the development of the ovaries of worker bees . It is also a powerful sex pheromone for drones on their wedding flight .

Brood detection pheromones are emitted by larvae and pupae and prevent worker bees from leaving the hive while there are still offspring to be cared for. Furthermore, they suppress the formation of the ovaries in the worker bees. The pheromones consist of a mixture of ten fatty acid esters , including glyceryl 1,2-dioleate-3-palmitate . Worker dolls contain 2 to 5 micrograms of the pheromone , drone dolls around 10, and queen dolls 30  micrograms .

Older, foraging worker bees release oleic acid ethyl ester , which inhibits the development of nurse bees and causes them to take longer to care for the brood. The oleic acid ester acts as a primer pheromone and stabilizes the relationship between brood-caring and food-procuring bees. The foragers produce it from nectar mixed with traces of ethanol , which they feed to the nurse bees. Their development is delayed until the number of older foragers decreases and thus the exposure of the nurse bees to oleic acid ethyl ester.

Box-terminating pheromones

The yellow-footed soil termite uses terpenes such as γ-cadinen and γ-cadinenal as primer pheromones that stimulate or inhibit box. These support the juvenile hormone in determining the position of totipotent workers in the caste system. In ants, the female larvae have bipotentiality for some time and thus the possibility of developing either as queens or workers. At a certain point in the larval development, further nutrition determines the fate of the larva. If the juvenile hormone titer is raised above a certain threshold, gynomorphs develop , otherwise workers. The larval feeding is controlled by a primer pheromone of the queen ant.

application

In the 19th century, the entomologist Étienne Léopold Trouvelot in Massachusetts escaped gypsy moths , which spread throughout the United States by the middle of the 20th century and are now among the most feared pests . As early as 1898, Edward Forbush and Charles Fernald made attempts to curb the gypsy moth population by attracting the males into traps that were occupied by attracting females. The United States Department of Agriculture continued these attempts through the 1930s, using extracts of female abdominal tips to attract male moths. The use of insect pheromones in plant protection has been intensively investigated, especially since the first syntheses, with the aim of developing environmentally friendly methods to control population dynamics .

Attractant trap for bark beetles

In crop protection, the use of pheromones in attractant traps to control insects is common practice. The insects can be attracted to kill them with an insecticide or physically, to catch them or for monitoring . Bark beetles are attracted with aggregation pheromones in order to trap them in traps. The attractant is usually released when drilling into the spruce wood and signals that the tree can be colonized. The bark beetle trap is an important tool for fighting bark beetles. The use of attractant traps, however, has the problem that the pheromone may act as a kairomone and thus attract predatory insects. By reducing the population of natural predators of the bark beetle, the pheromone trap is counterproductive in this case. Monitoring using attractant traps, such as window traps , is used to quantitatively record pests in order to control them more specifically with insecticides depending on the activity detected. They are also used to identify new species.

Catch trees work on the same principle as attractant traps. The bark beetles of the first infestation attract other conspecifics through aggregation pheromones. Storm wood , which can be equipped with pheromone dispensers to increase the attractiveness, is suitable as catching trees . The trees prepared in this way divert approaching bark beetles from the stand and bind them to controllable trunks. The use of trapping trees requires regular monitoring of the trees. When larval tunnels appear, the trees are debarked, with the larvae and pupae drying up. If necessary, the infested tree can be treated with insecticides or it is burned to prevent the next generation from outing.

Anti-egg-laying marker pheromones are widespread in the insect world. The possibility of controlling the population dynamics with these pheromones could be demonstrated in various experiments. The application of the egg-deposition-preventing marking pheromone of the cherry fruit flies , which can not be controlled with yellow tablets , for example , reduced the infestation of the cherries by 90%.

Another application is the confusion method or mating disorder. A high substance concentration of artificially produced pheromones is applied. As a result, it is no longer possible for the males to follow the pheromones of the females, which prevents the pest from multiplying. The confusion method is species-specific. With sufficient dispensers, it is usually successful with regard to one species, but in some cases related species occupy the ecological niche that is released .

Bees use the Nasanov pheromone to guide worker bees back to the hive. The pheromone contains terpenes such as geraniol and citral . Beekeepers use a man-made product to attract bees to an unused beehive. The method is suitable for catching Africanized honey bees in catch boxes.

toxicology

Toxicological studies were mainly carried out in connection with the approval of pheromone traps and dispensers. A health hazard cannot be assessed in general due to the great chemical diversity of the pheromones, but is usually ruled out because only small amounts are emitted. However, in higher doses, orally administered pheromones such as cantharidin rarely lead to death.

proof

Recording of an electroantennogram as a function of the odor flow concentration

The commercial application in crop protection intensified the investigation of pheromones and led to the development of highly sensitive analytical methods . There are several stages in identifying a pheromone. First, an extract of the pheromone is obtained. This is done according to the method already used by Butenandt of extracting glands or whole animals with an easily evaporable solvent , ideally at the time of high pheromone production. Alternatively, the pheromone is adsorbed on activated charcoal from the gas phase and an extract is obtained with a little solvent. Solid phase micro-extraction is suitable for very small traces . For identification, the extracts or the solid phase micro-extraction samples are examined by means of gas chromatography with mass spectrometry coupling .

The electroantennogram technique is suitable for investigating the biological activity of insect pheromones. An electrode placed in the main antenna trunk and an antenna branch measures the change in electrical voltage as a function of the concentration of pheromone molecules that hit the antenna and are transported to the antenna in a defined manner by an air stream. By varying the pheromone molecule, the influence of certain functional groups that interact with the chiral elements of the receptors can be determined .

The coupling of gas chromatography and electroantennogram allows the biological activity of the compounds present in an extract to be checked. The shape of the electroantennogram depends on the fragrance component in the air flow; the amplitude increases with the concentration and the flow speed of the air.

literature

Web links

Commons : Pheromones  - Collection of images, videos and audio files
Wiktionary: Pheromone  - explanations of meanings, word origins, synonyms, translations

Individual evidence

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