3-Amino-1,2,4-triazole
Chemical compound / From Wikipedia, the free encyclopedia
3-Amino-1,2,4-triazole (3-AT) is a heterocyclic organic compound that consists of a 1,2,4-triazole substituted with an amino group.
Names | |
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IUPAC name
1H-1,2,4-Triazol-3-amine | |
Other names
1,2,4-Triazol-3-amine aminotriazole Amitrol Amitrole 3-Aminotriazole 2-Amino-1,3,4-triazole | |
Identifiers | |
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3D model (JSmol) |
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Abbreviations | 3-AT |
107687 | |
ChEBI | |
ChEMBL | |
ChemSpider |
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ECHA InfoCard | 100.000.474 |
EC Number |
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200706 | |
KEGG |
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MeSH | Amitrole |
PubChem CID |
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RTECS number |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C2H4N4 | |
Molar mass | 84.08 |
Appearance | colorless/white crystals or powder[2] |
Odor | odorless |
Density | 1.138 g/mol |
Melting point | 157 to 159 °C (315 to 318 °F; 430 to 432 K) |
Boiling point | 347 |
28 g/100 mL | |
Solubility | soluble in acetonirile, chloroform, ethanol, methanol, methylene chloride negligible in ethyl acetate |
Vapor pressure | 3.13x10−9 mmHg |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
potential occupational carcinogen |
GHS labelling: | |
Warning | |
H361, H373, H411 | |
P201, P202, P260, P273, P281, P308+P313, P314, P391, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | Non-flammable |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
1,100 to 2,500 mg/kg |
NIOSH (US health exposure limits): | |
PEL (Permissible) |
none[2] |
REL (Recommended) |
Ca TWA 0.2 mg/m3[2] |
IDLH (Immediate danger) |
Ca/N.D.[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3-AT is a competitive inhibitor of the product of the HIS3 gene, imidazoleglycerol-phosphate dehydratase.[3][4] Imidazoleglycerol-phosphate dehydratase is an enzyme catalyzing the sixth step of histidine production.[5]
3-AT is also a nonselective systemic triazole 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 biocide ban proposed by the Swedish Chemicals Agency[6] and approved by the European Parliament on January 13, 2009.[7]