Atrazine

Atrazine is a chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer is Syngenta and it is one of the most widely used herbicides in the United States, Canadian, and 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.

Atrazine
Names
Preferred IUPAC name
6-Chloro-N2-ethyl-N4-(propan-2-yl)-1,3,5-triazine-2,4-diamine
Other names
Atrazine
1-Chloro-3-ethylamino-5-isopropylamino-2,4,6-triazine
2-Chloro-4-ethylamino-6-isopropylamino-s-triazine
6-Chloro-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.016.017
KEGG
UNII
  • 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
  • Clc1nc(nc(n1)NC(C)C)NCC
Properties
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
7 mg/100 mL
Hazards
Flash point noncombustible
NIOSH (US health exposure limits):
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 verify (what is YN ?)
Infobox references

At least two significant Canadian farm well studies showed that atrazine was the most common contaminant found. As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the U.S.: 44  Studies suggest it is an endocrine disruptor, an agent that can alter the natural hormonal system. However, 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". However, in their 2016 Refined Ecological Risk Assessment for Atrazine, it was stated that "it is difficult to make definitive conclusions about the impact of atrazine at a given concentration but multiple studies have reported effects to various endpoints at environmentally-relevant concentrations." EPA started a registration review in 2013.

The EPA's review has been criticized, and the safety of atrazine remains controversial. EPA has however stated that "If at any time EPA determines there are urgent human or environmental risks from atrazine exposure that require prompt attention, we will take appropriate regulatory action, regardless of the status of the registration review process."

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