489. Amitrole

Nomenclature

CAS number: 61-82-5
1H-1,2,4-Triazol-5-amine; 3-amino-1H-1,2,4-triazole; 3-amino-s-triazole; aminotriazole; ATA; ENT-25445; Amizol (CFPI); Cytrol; Weedazol (CFPI).
C2H4N4; mol wt 84.08.
C 28.57%, H 4.80%, N 66.64%.

Description and 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. Krller, Residue Rev. 12, 163-192 (1966). Review of carcinogenicity studies: IARC Monographs 7, 31-43 (1974).

Chemical structure

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 (Krller).

Derivative

Hydrochloride.
C2H4N4.HCl; mol wt 120.54.
C 19.93%, H 4.18%, N 46.48%, Cl 29.41%.

Properties

Crystals from alcohol, 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.