View source for Chemistry:3-Amino-1,2,4-triazole

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477217939
| Reference =<ref>[http://pmep.cce.cornell.edu/profiles/extoxnet/24d-captan/amitrole-ext.html EXTOXNET] – Herbicide fact sheet for amitrole</ref>
| ImageFile = Aminotriazole.png
| ImageSize = 150px
| IUPACName = 1''H''-1,2,4-Triazol-3-amine
| OtherNames = 1,2,4-Triazol-3-amine<br/>aminotriazole<br/>Amitrol<br/>Amitrole<br/>3-Aminotriazole<br/>2-Amino-1,3,4-triazole
|Section1={{Chembox Identifiers
| Abbreviations = 3-AT
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1577
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZF80H5GXUF
| InChIKey = KLSJWNVTNUYHDU-UHFFFAOYAV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KLSJWNVTNUYHDU-UHFFFAOYSA-N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 232801
| CASNo = 61-82-5
| CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 200-521-5
| PubChem = 1639
| SMILES = n1c[nH]nc1N
| InChI = 1/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6)
| RTECS = XZ3850000
| MeSHName = Amitrole
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 40036
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11261
| Beilstein = 107687
| Gmelin = 200706
}}
|Section2={{Chembox Properties
| Formula = C<sub>2</sub>H<sub>4</sub>N<sub>4</sub>
| MolarMass = 84.08
| Appearance = colorless/white crystals or powder<ref name=NIOSH/>
| Odor = odorless
| Density = 1.138&nbsp;g/mol
| MeltingPtC = 157 to 159
| MeltingPt_notes = 
| BoilingPt = 347
| BoilingPt_notes = 
| Solubility = 28 g/100 mL
| SolubleOther = soluble in acetonirile, [[Chemistry:Chloroform|chloroform]], [[Chemistry:Ethanol|ethanol]], [[Chemistry:Methanol|methanol]], methylene chloride <br/> negligible in [[Chemistry:Ethyl acetate|ethyl acetate]]
| Solvent = 
| VaporPressure = 3.13x10<sup>−9</sup> mmHg
| pKa = 
| pKb = }}
|Section7={{Chembox Hazards
| MainHazards = potential occupational carcinogen
| NFPA-H = 1
| NFPA-F = 0
| NFPA-R = 0
| NFPA-S =
| GHSPictograms = {{GHS08}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|361|373|411}}
| PPhrases = {{P-phrases|201|202|260|273|281|308+313|314|391|405|501}}
| FlashPt = Non-flammable
| AutoignitionPtC = 
| ExploLimits = 
| PEL = none<ref name=NIOSH>{{PGCH|0027}}</ref>
| REL = Ca TWA 0.2 mg/m<sup>3</sup><ref name=NIOSH/>
| IDLH = Ca/N.D.<ref name=NIOSH/>
| LD50 = 1,100 to 2,500 mg/kg
 }}
}}

'''3-Amino-1,2,4-triazole''' ('''3-AT''') is a [[Chemistry:Heterocyclic compound|heterocyclic]] [[Chemistry:Organic compound|organic compound]] that consists of a 1,2,4-triazole substituted with an [[Chemistry:Amine|amino group]].

3-AT is a competitive inhibitor of the product of the [[Biology:HIS3|HIS3]] gene, [[Biology:Imidazoleglycerol-phosphate dehydratase|imidazoleglycerol-phosphate dehydratase]].<ref name="pmid6990004">{{cite journal |vauthors=Brennan MB, Struhl K |title=Mechanisms of increasing expression of a yeast gene in Escherichia coli |journal=J. Mol. Biol. |volume=136 |issue=3 |pages=333–8 |year=1980 |pmid=6990004 |doi= 10.1016/0022-2836(80)90377-0}}</ref><ref name="pmid10852947">{{cite journal |vauthors=Joung JK, Ramm EI, Pabo CO |title=A bacterial two-hybrid selection system for studying protein-DNA and protein-protein interactions |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=97 |issue=13 |pages=7382–7 |year=2000 |pmid=10852947 |pmc=16554 |doi=10.1073/pnas.110149297 |bibcode=2000PNAS...97.7382J |doi-access=free }}</ref> Imidazoleglycerol-phosphate dehydratase is an enzyme catalyzing the sixth step of histidine production.<ref>{{Cite web |url=http://db.yeastgenome.org/cgi-bin/locus.pl?locus=his3 |title=Yeastgenome.org |access-date=2006-12-01 |archive-url=https://web.archive.org/web/20060505213339/http://db.yeastgenome.org/cgi-bin/locus.pl?locus=his3 |archive-date=2006-05-05 |url-status=dead }}</ref>

3-AT is also a nonselective systemic [[Chemistry:Triazole|triazole]] [[Biology:Herbicide|herbicide]] used on nonfood croplands to control annual grasses and broadleaf and aquatic weeds. It is not used on food crops because of its carcinogenic properties. As an herbicide, it is known as ''aminotriazole'', ''amitrole'' or ''amitrol''.

Amitrol was included in a [[Biology:Biocide|biocide]] ban proposed by the Swedish Chemicals Agency<ref>{{cite web|url=http://www.kemi.se/templates/News____5415.aspx |title=Interpretation of criteria for approval of active substances in the proposed EU plant protection regulation |date=2008-09-23 |publisher=Swedish Chemicals Agency (KemI) |access-date=2009-01-14 |archive-url=https://web.archive.org/web/20090101024604/http://www.kemi.se/templates/News____5415.aspx |archive-date=1 January 2009 |url-status=dead }}</ref> and approved by the European Parliament on January 13, 2009.<ref>{{cite web|url=http://www.europarl.europa.eu/news/expert/infopress_page/066-45937-012-01-03-911-20090112IPR45936-12-01-2009-2009-false/default_en.htm |title=MEPs approve pesticides legislation |date=2009-01-13 |access-date=2009-01-14 |archive-url=https://web.archive.org/web/20090125031216/http://www.europarl.europa.eu/news/expert/infopress_page/066-45937-012-01-03-911-20090112IPR45936-12-01-2009-2009-false/default_en.htm |archive-date=25 January 2009 |url-status=dead }}</ref>

== Applications in microbiology ==
By applying 3-AT to a yeast [[Biology:Cell culture|cell culture]] which is dependent upon a plasmid containing HIS3 to produce [[Chemistry:Histidine|histidine]] (i.e. its own HIS3 analogue is not present or nonfunctional), an increased level of HIS3 expression is required in order for the yeast cell to survive. This has proved useful in various two-hybrid system, where a high-affinity binding between two proteins (i.e., higher expression of the HIS3 gene) will allow the yeast cell to survive in media containing higher concentrations of 3-AT. This selection process is performed using selective media, containing no histidine.

== 1959 cranberry contamination ==
On November 9, 1959, the secretary of the United States Department of Health, Education, and Welfare Arthur S. Flemming announced that some of the 1959 crop was tainted with traces of the herbicide aminotriazole.<ref>{{cite news|title=Safe Cranberries to Go on Sale|url=https://news.google.com/newspapers?id=8YRFAAAAIBAJ&sjid=ybwMAAAAIBAJ&dq=cranberry%20aminotriazole&pg=6720%2C2153163|access-date=10 February 2012|newspaper=Dubuque Telegraph-Herald|date=19 November 1959}}</ref> The market for cranberries collapsed and growers lost millions of dollars.<ref>[https://www.nytimes.com/2007/03/28/opinion/28blum.html?th&emc=th New York Times website - Opinion section]</ref> However, Ocean Spray recovered by expanding the market for cranberry juice, which, although widely available for sale, was before then not popular. This ensured cranberry growers would not have to rely mostly on Thanksgiving and Christmas for sales, which was the case until the notorious 1959 incident.

== References ==
{{reflist}}
{{Herbicides}}


{{DEFAULTSORT:Amino-1, 2, 4-Triazole, 3-}}
[[Category:Enzyme inhibitors]]
[[Category:Herbicides]]
[[Category:Endocrine disruptors]]
[[Category:Triazoles]]

{{Sourceattribution|3-Amino-1,2,4-triazole}}