Atrazine

Atrazine

Names
IUPAC name 1-Chloro-3-ethylamino-5-isopropylamino-2,4,6-triazine
Other names Atrazine 2-Chloro-4-ethylamino-6-isopropylamino-s-triazine 6-Chloro-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine
Identifiers
CAS Number	1912-24-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15930 Y
ChEMBL	ChEMBL15063 Y
ChemSpider	2169 Y
DrugBank	DB07392 Y
ECHA InfoCard	100.016.017
KEGG	C06551 Y
PubChem	2256
UNII	QJA9M5H4IM Y
InChI InChI=1S/C8H14ClN5/c1-4-10-7-12-6(9)13-8(14-7)11-5(2)3/h5H,4H2,1-3H3,(H2,10,11,12,13,14) Y Key: MXWJVTOOROXGIU-UHFFFAOYSA-N Y InChI=1/C8H14ClN5/c1-4-10-7-12-6(9)13-8(14-7)11-5(2)3/h5H,4H2,1-3H3,(H2,10,11,12,13,14) Key: MXWJVTOOROXGIU-UHFFFAOYAJ
SMILES Clc1nc(nc(n1)NC(C)C)NCC
Properties
Chemical formula	C8H14ClN5
Molar mass	215.69 g·mol−1
Appearance	colorless solid
Density	1.187 g/cm3
Melting point	175 °C (347 °F; 448 K)
Boiling point	200 °C (392 °F; 473 K) decomposes
Solubility in water	7 mg/100 mL
Hazards
Flash point	noncombustible
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 5 mg/m3
IDLH (Immediate danger)	N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Atrazine is an herbicide of the triazine class. Atrazine is used to prevent pre- and postemergence broadleaf weeds in crops such as maize (corn) and sugarcane and on turf, such as golf courses and residential lawns. It is one of the most widely used herbicides in US and Australian agriculture. It was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could neither show that this could be prevented nor that these levels were safe.

As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the United States. Studies suggest it is an endocrine disruptor, an agent that can alter the natural hormonal system. In 2006 the U.S. Environmental Protection Agency (EPA) had stated that under the Food Quality Protection Act "the risks associated with the pesticide residues pose a reasonable certainty of no harm", and in 2007, the EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted. EPA's 2009 review concluded that "the agency’s scientific bases for its regulation of atrazine are robust and ensure prevention of exposure levels that could lead to reproductive effects in humans." EPA started a registration review in 2013.

The EPA's review has been criticized, and the safety of atrazine remains controversial.

Atrazine is an herbicide that is used to stop pre- and postemergence broadleaf and grassy weeds in crops such as sorghum, maize, sugarcane, lupins, pine, and eucalypt plantations, and triazine-tolerant canola.

In the United States as of 2014, atrazine was the second-most widely used herbicide after glyphosate, with 76 million pounds of it applied each year. Atrazine continues to be one of the most widely used herbicides in Australian agriculture. Its use was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe.