Atrazine

Atrazine
Atrazine
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 Edit this at Wikidata
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) checkY
    Key: MXWJVTOOROXGIU-UHFFFAOYSA-N checkY
  • 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[1]
7 mg/100 mL
Hazards
Flash point Noncombustible[1]
NIOSH (US health exposure limits):
PEL (Permissible)
 None[1]
REL (Recommended)
 TWA 5 mg/m3[1]
IDLH (Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Atrazine is a chlorinated herbicide of the triazine class.[2] It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn),[3] soybean[3] 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,[2] Canadian,[4] and Australian agriculture.[5] 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.[6][7]

At least two significant Canadian farm well studies showed that atrazine was the most common contaminant found.[4] As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the U.S.[8]: 44  Studies suggest it is an endocrine disruptor, an agent that can alter the natural hormonal system.[9] 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",[10] and in 2007, the EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted.[11] The EPA's 2009 review[12] 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".[13] 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."[14] EPA started a registration review in 2013.[15]

The EPA's review has been criticized, and the safety of atrazine remains controversial.[16][17][18] 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."[2]

  1. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0043". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b c "Ingredients Used in Pesticide Products-Atrazine". US Environmental Protection Agency. Archived from the original on 2022-05-06. Retrieved 2021-08-08.
  3. ^ a b "Water Info : What's In My Water?: Atrazine". DrinkTap.org. Archived from the original on 1 January 2018.
  4. ^ a b "Guidelines for Canadian Drinking Water Quality: Guideline Technical Document – Atrazine". Health Canada. 1 November 2011. Archived from the original on 5 November 2022. Retrieved 5 November 2022.
  5. ^ "Chemical Review: Atrazine". Australian Pesticides and Veterinary Medicines Authority. 2014-05-28. Archived from the original on 2015-02-11. Retrieved 2015-02-11.
  6. ^ European Commission. 2004/248/EC: Commission Decision of 10 March 2004 concerning the non-inclusion of atrazine in Annex I to Council Directive 91/414/EEC and the withdrawal of authorisations for plant protection products containing this active substance (Text with EEA relevance) (notified under document number C(2004) 731) Archived 15 March 2022 at the Wayback Machine Decision 2004/248/EC - Official Journal L 078, Decision 2004/248/EC. March 16, 2004: Quote: "(9) Assessments made on the basis of the information submitted have not demonstrated that it may be expected that, under the proposed conditions of use, plant protection products containing atrazine satisfy in general the requirements laid down in Article 5(1)(a) and (b) of Directive 91/414/EEC. In particular, available monitoring data were insufficient to demonstrate that in large areas concentrations of the active substance and its breakdown products will not exceed 0,1 μg/L in groundwater. Moreover, it cannot be assured that continued use in other areas will permit a satisfactory recovery of groundwater quality where concentrations already exceed 0,1 μg/L in groundwater. These levels of the active substance exceed the limits in Annex VI to Directive 91/414/EEC and would have an unacceptable effect on groundwater." (10) Atrazine should therefore not be included in Annex I to Directive 91/414/EEC. (11) Measures should be taken to ensure that existing authorisations for plant protection products containing atrazine are withdrawn within a prescribed period and are not renewed and that no new authorisations for such products are granted."
  7. ^ Danny Hakimfeb for the New York Times. February 23, 2015. A Pesticide Banned, or Not, Underscores Trans-Atlantic Trade Sensitivities Archived 2016-12-23 at the Wayback Machine
  8. ^ Gilliom RJ et al. US Geological Survey The Quality of Our Nation's Waters: Pesticides in the Nation's Streams and Ground Water, 1992–2001 Archived 2013-11-26 at the Wayback Machine March 2006, Revised February 15, 2007
  9. ^ Atrazine: Chemical Summary. Toxicity and Exposure Assessment for Children's Health (PDF) (Report). U.S. Environmental Protection Agency. 2007-04-24. Archived from the original (PDF) on 2012-03-16.
  10. ^ Triazine Cumulative Risk Assessment and Atrazine, Simazine, and Propazine Decisions Archived June 1, 2013, at the Wayback Machine, June 22, 2006, EPA.
  11. ^ Atrazine Updates: Amphibians Archived 2015-09-30 at the Wayback Machine, April 2010, EPA.
  12. ^ EPA Begins New Scientific Evaluation of Atrazine Archived 2016-03-04 at the Wayback Machine, October 7, 2009, EPA.
  13. ^ EPA Atrazine Updates: Scientific Peer Review—Human Health Archived 2015-09-30 at the Wayback Machine Current as of January 2013. Accessed March 15, 2014
  14. ^ "Refined Ecological Risk Assessment for Atrazine". EPA. p. 184. Archived from the original on 11 September 2020. Retrieved 12 October 2020.
  15. ^ EPA [ww.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#amphibian Atrazine Updates: Scientific Peer Review—Amphibians] Current as of January 2013. Accessed March 15, 2014
  16. ^ "A Valuable Reputation: Tyrone Hayes said that a chemical was harmful, its maker pursued him" Archived 2014-07-02 at the Wayback Machine by Rachel Aviv, The New Yorker, 10 February 2014
  17. ^ Duhigg, Charles (August 22, 2009). "Debating How Much Weed Killer Is Safe in Your Water Glass". The New York Times. Archived from the original on 2018-11-07. Retrieved 2015-05-02.
  18. ^ Tillitt DE, Papoulias DM, Whyte JJ, Richter CA (2010). "Atrazine reduces reproduction in fathead minnow (Pimephales promelas)". Aquat. Toxicol. 99 (2): 149–59. doi:10.1016/j.aquatox.2010.04.011. PMID 20471700. Archived from the original on 2022-03-15. Retrieved 2020-09-01.