Amitrole

Title: Amitrole
CAS Registry Number: 61-82-5
CAS Name: 1H-1,2,4-Triazol-3-amine
Additional Names: 3-amino-1H-1,2,4-triazole; aminotriazole; ATA
Manufacturers' Codes: ENT-25445
Trademarks: Amizol (CFPI); Cytrol; Weedazol (CFPI)
Molecular Formula: C2H4N4
Molecular Weight: 84.08
Percent Composition: C 28.57%, H 4.80%, N 66.64%
Literature References: Non-selective post-emergence, translocated herbicide. Prepn: G. Sjostedt, L. Gringas, Org. Synth. coll. vol. III, 95 (1955). Use as herbicide: Allen, US 2670282 (1954 to Am. Chemical Paint Co.). Antithyroid activity: T. H. Jukes, C. B. Shaffer, Science 132, 296 (1960). Review: E. Kröller, Residue Rev. 12, 163-192 (1966). Review of carcinogenicity studies: IARC Monographs 7, 31-43 (1974).
Properties: Crystals from abs ethanol, mp 159°. Soluble in water, methanol, ethanol, chloroform. Sparingly sol in ethyl acetate. Insol in ether, acetone. Aq solns are neutral. LD50 in mice, rats (g/kg): 14.7, 25.0 orally (Kröller).
Melting point: mp 159°
Toxicity data: LD50 in mice, rats (g/kg): 14.7, 25.0 orally (Kröller)
Derivative Type: Hydrochloride
Molecular Formula: C2H4N4.HCl
Molecular Weight: 120.54
Percent Composition: C 19.93%, H 4.18%, N 46.48%, Cl 29.41%
Properties: Crystals from alcohol, mp 153°.
Melting point: mp 153°
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin; dyspnea, muscle spasms, ataxia, anorexia, salivation, increased body temperature; lassitude, skin dryness and depression associated with thyroid function suppression. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 14. Amitrole is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-16.
Use: Herbicide.
Amixetrine Amlexanox Amlodipine Ammonia Ammonia Water

3-Amino-1,2,4-triazole[1]
Aminotriazole.png
Identifiers
Abbreviations 3-AT
CAS number 61-82-5 YesY
ChemSpider 1577 YesY
UNII ZF80H5GXUF YesY
EC number 200-521-5
KEGG C11261 YesY
ChEBI CHEBI:40036 YesY
ChEMBL CHEMBL232801 YesY
RTECS number XZ3850000
Jmol-3D images Image 1
Properties
Molecular formula C2H4N4
Molar mass 84.08
Density 1.138 g/mol
Melting point 157-159 °C
Solubility in water 280 g/liter
Hazards
R-phrases R48/22 R51/53 R63
S-phrases (S2) S13 S36/37 S61
Flash point Non-flammable
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.

3-AT is a competitive inhibitor of the product of the HIS3 gene, imidazoleglycerol-phosphate dehydratase.[2] Imidazoleglycerol-phosphate dehydratase is an enzyme catalysing the sixth step of histidine production.[3]

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 [4] and approved by the European Parliament on January 13, 2009.[5]