871. Atrazine

Nomenclature

CAS number: 1912-24-9
6-Chloro-N2-ethyl-N4-(1-methylethyl)-1,3,5-triazine-2,4-diamine; 2-chloro-4-ethylamino-6-isopropylamine-s-triazine; G-30027; AAtrex (Syngenta); Atranex (Makhteshim-Agan); Gesaprim (Syngenta).
C8H14ClN5; mol wt 215.68.
C 44.55%, H 6.54%, Cl 16.44%, N 32.47%.

Description and references

Prepn: Gysin, Knüsli, CH 342784, CH 342785 (both 1960 to Geigy), C.A. 55, 5552d (1961); Mel'nikov et al., Khim. Prom. 1961, 703, C.A. 58, 526c (1963); Andriska et al., HU 149189 (1962 to Nehézvegyipari Kutato Intézet), C.A. 58, 13972c (1963); Mildner, FR 1317812 (1963 to Radonja Kemijska Ind.), C.A. 59, 8765h (1963). Toxicity study: S. Dalgaard-Mikkelsen, E. Poulsen, Pharmacol. Rev. 14, 225 (1962) PubMed. Review of toxicology and human exposure: Toxicological Profile for Atrazine (PB2004-100001, 2003) 262 pp.

Chemical structure

Properties

Crystals, mp 171-174°. Soly at 25° in water 34.5 ppm; ether 12,000 ppm; chloroform 52,000 ppm; methanol 18,000 ppm. Stable in slightly acidic or basic media; hydrolyzed to inactive hydroxy deriv by alkali or mineral acids. LD50 orally in mice: 1750 mg/kg (Dalgaard-Mikkelsen, Poulsen).

Caution

Potential symptoms of overexposure are irritation of eyes and skin; dermatitis, skin sensitization; dyspnea, weakness, incoordination, salivation; hypothermia; liver injury. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 22.

Use

Selective herbicide.