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Revision as of 17:46, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 476145692 of page 3-Amino-1,2,4-triazole for the Chem/Drugbox validation project (updated: '').  Latest revision as of 12:31, 20 September 2024 edit RustyOldShip (talk | contribs)Extended confirmed users503 edits herbicide resistance group 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443317127
| Watchedfields = changed
⚫ | Reference = <ref> - Herbicide fact sheet for amitrole</ref>
⚫ | verifiedrevid = 477217939
⚫ | Reference =<ref> – Herbicide fact sheet for amitrole</ref>
| ImageFile = Aminotriazole.png | ImageFile = Aminotriazole.png
| ImageSize = 150px | ImageSize = 150px
| IUPACName = 3-Amino-1,2,4-triazole | IUPACName = 1''H''-1,2,4-Triazol-3-amine
| OtherNames = 1,2,4-Triazol-3-amine<br>aminotriazole<br>Amitrol<br>Amitrole | 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 |Section1={{Chembox Identifiers
| Abbreviations = 3-AT | Abbreviations = 3-AT
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChEMBL = 232801 | ChEMBL = 232801
| CASNo = 61-82-5 | CASNo = 61-82-5
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 200-521-5 | EINECS = 200-521-5
| PubChem = | PubChem = 1639
| SMILES = n1cnnc1N | SMILES = n1cnc1N
| InChI = 1/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6) | InChI = 1/C2H4N4/c3-2-4-1-5-6-2/h1H,(H3,3,4,5,6)
| RTECS = XZ3850000 | RTECS = XZ3850000
| MeSHName = | MeSHName = Amitrole
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 40036 | ChEBI = 40036
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11261 | KEGG = C11261
| Beilstein = 107687
| ATCCode_prefix =
| Gmelin = 200706
| ATCCode_suffix =
}}
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=2 | H=4 | N=4
| Formula = C<sub>2</sub>H<sub>4</sub>N<sub>4</sub>
| Appearance = colorless/white crystals or powder<ref name=NIOSH/>
| MolarMass = 84.08
| Odor = odorless
| Appearance =
| Density = 1.138 g/mol | Density = 1.138&nbsp;g/mL
| MeltingPt = 157 - 159 °C | MeltingPtC = 157 to 159
| MeltingPt_notes =
| Melting_notes =
| BoilingPt = | BoilingPt = 347
| Boiling_notes = | BoilingPt_notes =
| Solubility = 280 gm/liter | Solubility = 28 g/100 mL
| SolubleOther = soluble in ], ], ], ], ] <br/> negligible in ]
| SolubleOther =
| Solvent = | Solvent =
| VaporPressure = 3.13x10<sup>−9</sup> mmHg
| pKa = | pKa =
| pKb = }} | pKb = }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| MainHazards = potential occupational carcinogen
| EUClass =
| EUIndex = | NFPA-H = 1
| MainHazards = | NFPA-F = 0
| NFPA-H = | NFPA-R = 0
| NFPA-F = | NFPA-S =
| GHSPictograms = {{GHS08}}{{GHS09}}
| NFPA-R =
| GHSSignalWord = Warning
| NFPA-O =
| HPhrases = {{H-phrases|361|373|411}}
| RPhrases = {{R48/22}} {{R51/53}} {{R63}}
| PPhrases = {{P-phrases|201|202|260|273|281|308+313|314|391|405|501}}
| SPhrases = {{S2}} {{S13}} {{S36/37}} {{S61}}
⚫ | FlashPt = Non-flammable
| RSPhrases =
| AutoignitionPtC =
⚫ | FlashPt = Nonflammable
| Autoignition =
| ExploLimits = | ExploLimits =
| PEL = }} | 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 ] ] that consists of ] with an ] as a ].

3-AT is a competitive inhibitor of the product of the ] gene, ].<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 ] ] used on nonfood ]s to control ] grasses and ] and aquatic ]s. It is not used on ] ] because of its ] properties. As an herbicide, it is known as ''aminotriazole'', ''amitrole'' or ''amitrol''.

Amitrol was included in a ] ban proposed by the ]<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> Amitrol's mode of action is unknown, though it is classed as a ] Q herbicide.<ref>{{cite web |title=Australia Herbicide Classification Lookup |url=https://hracglobal.com/tools/australia-classification-lookup/ |website=Herbicide Resistance Action Committee |language=en}}</ref>

== Applications in microbiology ==
By applying 3-AT to a yeast ] which is dependent upon a plasmid containing HIS3 to produce ] (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 ], containing no histidine.

== 1959 cranberry contamination ==
On November 9, 1959, the secretary of the ], ], announced that ] 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></ref> However, ] 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 1959 incident.

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

{{Authority control}}

{{DEFAULTSORT:Amino-1, 2, 4-Triazole, 3-}}
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