Semiochemical

{{main|Pheromone}}

A pheromone (from Greek phero "to bear" + hormone from Greek – "impetus") is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual.{{Cite web|title = Pheromone|url = http://www.medterms.com/script/main/art.asp?articlekey=12896|website = MedicineNet|access-date = 2015-11-05|archive-date = 2011-05-11|archive-url = https://web.archive.org/web/20110511134143/http://www.medterms.com/script/main/art.asp?articlekey=12896|url-status = dead}} There are alarm pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology.{{Cite journal|title = Peptide pheromone-dependent regulation of antimicrobial peptide production in Gram-positive bacteria: a case of multicellular behavior|journal = Peptides|date = 2001-10-01|pages = 1579–1596|volume = 22|series = Bacterial and anti bacterial peptides|issue = 10|doi = 10.1016/S0196-9781(01)00493-4|first1 = Michiel|last1 = Kleerebezem|first2 = Luis E.|last2 = Quadri|pmid=11587786| s2cid=38943224 }} Their use among insects has been particularly well documented. In addition, some vertebrates and plants communicate by using pheromones. A notable example of pheromone usage to indicate sexual receptivity in insects can be seen in the female Dawson's burrowing bee, which uses a particular mixture of cuticular hydrocarbons to signal sexual receptivity to mating, and then another mixture to indicate sexual disinterest. These hydrocarbons, in association with other chemical signals produced in the Dufour's gland, have been implicated in male repulsion signaling as well.{{Cite journal|title = The role of cuticular hydrocarbons in male attraction and repulsion by female Dawson's burrowing bee, Amegilla dawsoni|journal = Animal Behaviour|date = 2003-10-01|pages = 677–685|volume = 66|issue = 4|doi = 10.1006/anbe.2003.2240|first1 = Leigh W.|last1 = Simmons|first2 = John|last2 = Alcock|first3 = Anthony|last3 = Reeder| s2cid=53176275 }}

The term "pheromone" was introduced by Peter Karlson and Martin Lüscher in 1959, based on the Greek word pherein (to transport) and hormone (to stimulate).{{Cite journal|title = 'Pheromones': a New Term for a Class of Biologically Active Substances|journal = Nature|date = 1959-01-03|pages = 55–56|volume = 183|issue = 4653|doi = 10.1038/183055a0|language = en|first1 = P.|last1 = Karlson|first2 = M.|last2 = Lüscher|pmid=13622694| bibcode=1959Natur.183...55K | s2cid=4243699 }} They are also sometimes classified as ecto-hormones.{{Cite journal|title = Human pheromones: integrating neuroendocrinology and ethology|journal = Neuro Endocrinology Letters|date = 2001-10-01|issn = 0172-780X|pmid = 11600881|pages = 309–321|volume = 22|issue = 5|first1 = J. V.|last1 = Kohl|first2 = M.|last2 = Atzmueller|first3 = B.|last3 = Fink|first4 = K.|last4 = Grammer}} German Biochemist Adolf Butenandt characterized the first such chemical, Bombykol (a chemically well-characterized pheromone released by the female silkworm to attract mates).{{Cite journal|title = Über den Sexuallockstoff des Seidenspinners, I. Der biologische Test und die Isolierung des reinen Sexuallockstoffes Bombykol|journal = Hoppe-Seyler's Zeitschrift für Physiologische Chemie|pages = 71–83|volume = 324|issue = Jahresband|doi = 10.1515/bchm2.1961.324.1.71|first1 = Adolf|last1 = Butenandt|first2 = Rüdiger|last2 = Beckmann|first3 = Erich|last3 = Hecker|year = 2009|pmid = 13689417}}

{{main|Allomone}}

An allomone is any chemical substance released by an individual of one species that affects the behavior of a member of another species to the benefit of the originator but not the receiver.{{Cite encyclopedia

| contribution=Chemical Ecology

| author=Grasswitz, T.R. and G.R. Jones

| title=Encyclopedia of Life Sciences | date=2002 | publisher= John Wiley & Sons, Ltd

| doi=10.1038/npg.els.0001716

| title-link=Encyclopedia of Life Sciences

| isbn=978-0470016176

}} Production of allomones is a common form of defense, such as by plant species against insect herbivores or prey species against predators. Sometimes species produce the sex pheromones of the organisms they exploit as prey or pollinators (such as bolas spiders{{cite journal|author=Haynes, K.F., C. Gemeno, and K.V. Yeargan|year=2002|title=Aggressive chemical mimicry of moth pheromones by a bolas spider: how does this specialist predator attract more than one species of prey?|journal=Chemoecology|volume=12|issue=2|pages=99–105|doi=10.1007/s00049-002-8332-2|bibcode=2002Checo..12...99H |s2cid=41663936 }} and some orchids{{cite journal | last1 = Ayasse | first1 = M | year = 2010 | title = Chemical Ecology in deceptive orchids | journal = Chemoecology | volume = 20 | pages = 171–178 }}). Male sex pheromone of Dacini fruit flies, besides acting as aggregation pheromone to form lek, also acts as an allomone to deter lizard predation.Tan, K.H. (2000) Sex pheromonal components in the defense of the melon fly, Bactrocera cucurbitae, against Asian House gecko, Hemidactylus frenatus. Journal of Chemical Ecology, 26: 697-704. Wee, S.L. and Tan, K.H. (2001) Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus. Journal of Chemical Ecology, 27: 953-964. Wee, S. L. and Tan, K. H. (2005) Male endogenous pheromonal component of Bactrocera carambolae (Diptera:Tephritidae) deterred gecko predation. Chemoecology, 15: 199-203. The term "Allomone" was proposed by Brown, Eisner, and Whittaker{{cite journal | last1 = Brown | first1 = W.L. | last2 = Eisner | first2 = T. | last3 = Whittaker | first3 = W.H. | year = 1970 | title = Allomones and kairomones: Transspecific chemical messengers | journal = BioScience | volume = 20 | issue = 1| pages = 21–22 | doi=10.2307/1294753| jstor = 1294753 | citeseerx = 10.1.1.1018.593 }} to denote those substances which confer an advantage upon the emitter.

{{main|Kairomone}}

A kairomone is a semiochemical, emitted by an organism, which mediates interspecific interactions in a way that benefits an individual of another species which receives it, without benefitting the emitter. Two main ecological cues are provided by kairomones; they generally either indicate a food source for the receiver, or give warning of the presence of a predator. Often a pheromone may be utilized as a kairomone by a predator or parasitoid to locate the emitting organism.{{cite journal|author1=Zuk, M. |author2=Kolluru G.R. |name-list-style=amp |year=1998|title=Exploitation of sexual signals by predators and parasitoids|journal=The Quarterly Review of Biology|volume=73|issue=4 |pages=415–438|doi=10.1086/420412|s2cid=19287833 }}

A synomone is an interspecific semiochemical that is beneficial to both interacting organisms, the emitter and receiver, e.g. floral synomone of certain Bulbophyllum species (Orchidaceae) attracts fruit fly males (Tephritidae: Diptera) as pollinators, so can be classed as an attractant. In this true mutualistic inter-relationship, both organisms gain benefits in their respective sexual reproductive systems – i.e. orchid flowers are pollinated and the Dacini fruit fly males are rewarded with a sex pheromone precursor or booster. The floral synomone, also acts as a reward to pollinators, is either in the form of a phenylpropanoid (e.g. methyl eugenol{{cite journal|author=Tan, K.H., R. Nishida and Y.C. Toong|year=2002|title=Bulbophyllum cheiri's floral synomone lures fruit flies to perform pollination.|journal=Journal of Chemical Ecology|volume=28|issue=6|pages=1161–1172|doi=10.1023/A:1016277500007|pmid=12184394 |s2cid=36621985 }}{{cite journal|author1=Nishida, R., K.H. Tan, S.L. Wee, A.K.W. Hee and Toong, Y. C.|year=2004|title=Phenylpropanoids in the fragrance of the fruit fly orchid, Bulbophyllum cheiri, and their relationship to the pollinator, Bactrocera papayae.|journal= Biochemical Systematics and Ecology|volume=32|issue=3|pages=245–252|doi=10.1016/S0305-1978(03)00179-0|bibcode=2004BioSE..32..245N }}{{cite journal|author1=Tan, K.H., L.T. Tan, and R. Nishida|year=2006|title=Floral phenylpropanoid cocktail and architecture of Bulbophyllum vinaceum orchid in attracting fruit flies for pollination.|journal=Journal of Chemical Ecology|volume=32|issue=11|pages=2429–2441|doi=10.1007/s10886-006-9154-4|pmid=17082990|bibcode=2006JCEco..32.2429T |s2cid=15812115 }}) or a phenylbutanoid (e.g. raspberry ketone{{cite journal|author1=Tan, K.H. |author2= Nishida, R. |year=2005|title=Synomone or Kairomone? - Bulbophyllum apertum (Orchidaceae) flower releases raspberry ketone to attract Bactrocera fruit flies.|journal=Journal of Chemical Ecology|volume=31|issue= 3 |pages=509–519|pmid= 15898497|doi=10.1007/s10886-005-2023-8 |s2cid= 39173699 }} and zingerone{{cite journal|author1=Tan, K.H. and R. Nishida|year=2000|title=Mutual reproductive benefits between a wild orchid, Bulbophyllum patens, and Bactrocera fruit flies via a floral synomone.|journal=Journal of Chemical Ecology|volume=26|issue=2|pages=533–546|doi=10.1023/A:1005477926244|bibcode=2000JCEco..26..533T |s2cid=24971928 }}{{cite journal|author1=Tan, K.H. and R. Nishida |year=2007|title=Zingerone in the floral synomone of Bulbophyllum baileyi (Orchidaceae) attracts Bactrocera fruit flies during pollination|journal= Biochemical Systematics and Ecology|volume=35|issue=6|pages=334–341|doi=10.1016/j.bse.2007.01.013|bibcode=2007BioSE..35..334T }}).

Another example of a synomone is trans-2-hexenal, emitted by trees in the Mimosa / Acacia clade of the Fabaceae. These trees form distinctive hollow structures in which ants nest. When a leaf is disrupted by an herbivore, the damaged cells emit trans-2-hexenal (among other volatiles), which is detected by the ants. The ants swarm to the herbivore, biting and stinging to defend their host plant. The tree repays them in turn by providing sugary nectar and fat- and protein-rich Beltian bodies to feed the ant colony.

The goals of using semiochemicals in pest control are

1. to monitor pest populations to determine if control is warranted and
2. to alter the behavior of the pest or its enemies to the detriment of the pest. In general, the advantages of using semiochemicals are
3. they have adverse effects only on target pests,
4. they are relatively nontoxic and required in low amounts,
5. they are nonpersistent and environmentally safe
6. they appear difficult for insects to develop resistance against. Monitoring of pest populations with pheromones is often integrated in management programs.

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{{Wiktionary}}

• {{cite journal|title=A Survey of Identified Kairomones and Synomones Used by Insect Parasitoids to Locate and Accept Their Hosts | doi=10.1007/BF01245964 | volume=7|issue = 3|journal=Chemoecology|pages=121–131 | last1 = Rutledge | first1 = Claire E.|year = 1996| bibcode=1996Checo...7..121R | s2cid=40129088 }}
• [http://www.helsinki.fi/kemia/opettaja/aineistot/hyonteistenkemiaa/english/printable_semiochemicals.pdf Article on Semiochemicals], helsinki.fi

Category:Chemical ecology