Atrazine

Title: Atrazine
CAS Registry Number: 1912-24-9
CAS Name: 6-Chloro-N-ethyl-N¢-(1-methylethyl)-1,3,5-triazine-2,4-diamine
Additional Names: 2-chloro-4-ethylamino-6-isopropylamine-s-triazine
Manufacturers' Codes: G-30027
Trademarks: AAtrex (Syngenta); Atranex (Makhteshim-Agan); Gesaprim (Syngenta)
Molecular Formula: C8H14ClN5
Molecular Weight: 215.68
Percent Composition: C 44.55%, H 6.54%, Cl 16.44%, N 32.47%
Literature 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). Review of toxicology and human exposure: Toxicological Profile for Atrazine (PB2004-100001, 2003) 262 pp.
Properties: Crystals, mp 171-174°. Soly at 25° in water 70 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).
Melting point: mp 171-174°
Toxicity data: 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.
Atrial Natriuretic Peptide Atrolactamide Atrolactic Acid Atropic Acid Attacins

Atrazine
Atrazine
Atrazine
Identifiers
CAS number 1912-24-9 YesY
PubChem 2256
ChemSpider 2169 YesY
UNII QJA9M5H4IM YesY
DrugBank DB07392
KEGG C06551 YesY
ChEBI CHEBI:15930 YesY
ChEMBL CHEMBL15063 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H14ClN5
Molar mass 215.68 g mol−1
Appearance colorless solid
Density 1.187 gcm−3
Melting point 175 °C; 347 °F; 448 K
Boiling point 200 °C; 392 °F; 473 K
Solubility in water 7 mg/100 mL
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Atrazine is a herbicide of the triazine class. It is the most widely used herbicide in the United States[1] and one of the most widely used herbicides in Australian agriculture.[2] It was banned in the European Union in 2004.[3] Atrazine is used to prevent pre and post-emergence broadleaf weeds in crops such as maize (corn) and sugarcane and on turf, such as golf courses and residential lawns.

Atrazine is the most commonly detected contaminant of drinking water in the United States. It is a potential endocrine disruptor, an agent that may alter the natural hormonal system in animals.[1][4] In 2006 the U.S. Environmental Protection Agency (EPA) stated that "the risks associated with the pesticide residues pose a reasonable certainty of no harm",[5] and in 2007 the EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted.[6] However, in 2009 the EPA began a new scientific evaluation of health effects on atrazine.[7] Numerous studies have stated that atrazine has substantial adverse reproductive effects even at levels said by the EPA to be safe.[8][9][4][10]