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'''Atrazine '''is a [[herbicide]] of the [[triazine]] class. Atrazine is used to prevent pre and post-emergence broadleaf [[weed]]s in crops such as [[maize]] (corn) and [[sugarcane]] and on turf, such as golf courses and residential lawns.
'''Atrazine '''is a [[herbicide]] of the [[triazine]] class. Atrazine is used to prevent pre and post-emergence broadleaf [[weed]]s 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<ref name=yorker/> and in Australian agriculture.<ref name="APVMAmain">{{cite web|url=http://apvma.gov.au/node/12371|title=Chemical Review: Atrazine|publisher=Australian Pesticides and Veterinary Medicines Authority|accessdate=2015-02-11}}</ref> It was banned in the [[European Union]] in 2004 because of persistent groundwater contamination.<ref name="EDEXIM Substance Information">{{cite web|url=http://edexim.jrc.ec.europa.eu/list_annex_chemical_details.php?type=S&annex=108&id_part=1 |title=EDEXIM Chemical Information for Atrazine |accessdate=2014-02-10}}</ref>
It is one of the most widely used herbicides in US<ref name=yorker/> and in Australian agriculture.<ref name="APVMAmain">{{cite web|url=http://apvma.gov.au/node/12371|title=Chemical Review: Atrazine|publisher=Australian Pesticides and Veterinary Medicines Authority|accessdate=2015-02-11}}</ref> It was banned in the [[European Union]] in 2004.


As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the United States.<ref name=USGS>Gilliom RJ et al. US Geological Survey [http://pubs.usgs.gov/circ/2005/1291/pdf/circ1291_chapter4.pdf The Quality of Our Nation’s Waters: Pesticides in the Nation’s Streams and Ground Water, 1992–2001] March 2006, Revised February 15, 2007</ref>{{rp|42}} Studies suggest it is an [[endocrine disruptor]], an agent that may alter the natural hormonal system in animals.<ref name=AtrazineChemSummEPA>{{Cite report | author= | date = 2007-04-24 | title = Atrazine: Chemical Summary. Toxicity and Exposure Assessment for Children’s Health | url = http://www.epa.gov/teach/chem_summ/Atrazine_summary.pdf| publisher = U.S. Environmental Protection Agency }}</ref><ref name="Hayes et al 2011">{{cite journal|last=Hayes|first=Tyrone B.|coauthors=Anderson, Lloyd L.; Beasley, Val R.; de Solla, Shane R.; Iguchi, Taisen; et al.|title=Demasculinization and feminization of male gonads by atrazine: Consistent effects across vertebrate classes|journal=The Journal of Steroid Biochemistry and Molecular Biology|year=2011|volume=127|issue=1–2|pages=64–73|doi=10.1016/j.jsbmb.2011.03.015|pmid=21419222}}</ref> In 2006 the U.S. [[United States Environmental Protection Agency|Environmental Protection Agency]] (EPA) stated that "the risks associated with the pesticide residues pose a reasonable certainty of no harm",<ref name="EPATriazine">[http://www.epa.gov/oppsrrd1/cumulative/triazine_fs.htm Triazine Cumulative Risk Assessment and Atrazine, Simazine, and Propazine Decisions], June 22, 2006, EPA.</ref> and in 2007 EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted.<ref name=EPAUpdateAmphib>[http://www.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#amphibian Atrazine Updates: Amphibians], April 2010, EPA.</ref> EPA opened a new review in 2009<ref name="EPAPress">[http://yosemite.epa.gov/opa/admpress.nsf/d0cf6618525a9efb85257359003fb69d/554b6abea9d0672f85257648004a88c1!OpenDocument EPA Begins New Scientific Evaluation of Atrazine], October 7, 2009, EPA.</ref> that 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."<ref name="AtraUpdateHealth">EPA [http://www.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#atrazine Atrazine Updates: Scientific Peer Review—Human Health] Current as of January 2013. Accessed March 15, 2014</ref>
As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the United States.<ref name=USGS>Gilliom RJ et al. US Geological Survey [http://pubs.usgs.gov/circ/2005/1291/pdf/circ1291_chapter4.pdf The Quality of Our Nation’s Waters: Pesticides in the Nation’s Streams and Ground Water, 1992–2001] March 2006, Revised February 15, 2007</ref>{{rp|42}} Studies suggest it is an [[endocrine disruptor]], an agent that may alter the natural hormonal system in animals.<ref name=AtrazineChemSummEPA>{{Cite report | author= | date = 2007-04-24 | title = Atrazine: Chemical Summary. Toxicity and Exposure Assessment for Children’s Health | url = http://www.epa.gov/teach/chem_summ/Atrazine_summary.pdf| publisher = U.S. Environmental Protection Agency }}</ref><ref name="Hayes et al 2011">{{cite journal|last=Hayes|first=Tyrone B.|coauthors=Anderson, Lloyd L.; Beasley, Val R.; de Solla, Shane R.; Iguchi, Taisen; et al.|title=Demasculinization and feminization of male gonads by atrazine: Consistent effects across vertebrate classes|journal=The Journal of Steroid Biochemistry and Molecular Biology|year=2011|volume=127|issue=1–2|pages=64–73|doi=10.1016/j.jsbmb.2011.03.015|pmid=21419222}}</ref> In 2006 the U.S. [[United States Environmental Protection Agency|Environmental Protection Agency]] (EPA) stated that "the risks associated with the pesticide residues pose a reasonable certainty of no harm",<ref name="EPATriazine">[http://www.epa.gov/oppsrrd1/cumulative/triazine_fs.htm Triazine Cumulative Risk Assessment and Atrazine, Simazine, and Propazine Decisions], June 22, 2006, EPA.</ref> and in 2007 EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted.<ref name=EPAUpdateAmphib>[http://www.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#amphibian Atrazine Updates: Amphibians], April 2010, EPA.</ref> EPA opened a new review in 2009<ref name="EPAPress">[http://yosemite.epa.gov/opa/admpress.nsf/d0cf6618525a9efb85257359003fb69d/554b6abea9d0672f85257648004a88c1!OpenDocument EPA Begins New Scientific Evaluation of Atrazine], October 7, 2009, EPA.</ref> that 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."<ref name="AtraUpdateHealth">EPA [http://www.epa.gov/pesticides/reregistration/atrazine/atrazine_update.htm#atrazine Atrazine Updates: Scientific Peer Review—Human Health] Current as of January 2013. Accessed March 15, 2014</ref>

Revision as of 13:13, 19 April 2015

Atrazine
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
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).

Atrazine is a herbicide of the triazine class. 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.

It is one of the most widely used herbicides in US[2] and in Australian agriculture.[3] It was banned in the European Union in 2004.

As of 2001, atrazine was the most commonly detected pesticide contaminating drinking water in the United States.[4]: 42  Studies suggest it is an endocrine disruptor, an agent that may alter the natural hormonal system in animals.[5][6] 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",[7] and in 2007 EPA said that atrazine does not adversely affect amphibian sexual development and that no additional testing was warranted.[8] EPA opened a new review in 2009[9] that 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."[10]

EPA's review was criticized,[2] and atrazine's safety remains controversial.[2][6][11][12]

Uses

Atrazine is an herbicide that is used to stop pre and post-emergence broadleaf and grassy weeds in crops such as sorghum, maize, sugarcane, lupins, pine and eucalypt plantations, and triazine tolerant (TT) canola.[3]

In the United States as of 2014, atrazine was the second most widely used herbicide after glyphosate,[2] with 76 million pounds of it applied each year.[13][14] Atrazine continues to be one of the most widely used herbicides in Australian agriculture.[3] Its use was banned in the European Union in 2004, when the EU found that the data provided by the manufacturer was insufficient to show that groundwater and soil contamination would not exceed acceptable limits under the intended uses for atrazine.[15][16]: 4 [17]

Its effect on corn yields has been estimated from 8% to 1%, with 3–4% being the conclusion of one economics review.[18][19] In another study looking at combined data from 236 university corn field trials from 1986–2005, atrazine treatments showed an average of 5.7 bushels more per acre than alternative herbicide treatments.[20] Effects on sorghum yields have been estimated to be as high as 20%, owing in part to the absence of alternative weed control products that can be used on sorghum.[21]

Chemistry and biochemistry

Atrazine was invented in 1958 in the Geigy laboratories as the second of a series of 1,3,5-triazines.[22]

Atrazine is prepared from cyanuric chloride, which is treated sequentially with ethylamine and isopropyl amine. Like other triazine herbicides, atrazine functions by binding to the plastoquinone-binding protein in photosystem II, which animals lack. Plant death results from starvation and oxidative damage caused by breakdown in the electron transport process. Oxidative damage is accelerated at high light intensity.[23]

Atrazine's effects in humans and animals primarily involve the endocrine system. Studies suggest that atrazine is an endocrine disruptor that can cause hormone imbalance.[5]

Biodegradation

Atrazine biodegradation. Atrazine chlorohydrolase pathway.

Atrazine remains in soil for a matter of months (although in some soils can persist to at least 4 years)[5] and can migrate from soil to groundwater; once in groundwater, it degrades slowly. It has been detected in groundwater at high levels in some regions of the U.S. where it is used on some crops and turf. The US Environmental Protection Agency expresses concern regarding contamination of surface waters (lakes, rivers, and streams).[5]

Atrazine degrades in soil primarily by the action of microbes. The half-life of atrazine in soil ranges from 13 to 261 days.[24] Atrazine biodegradation can occur by two known pathways:

  1. Hydrolysis of the C-Cl bond, followed by the ethyl and isopropyl groups, catalyzed by the hydrolase enzymes called AtzA, AtzB, and AtzC. The end product of this process is cyanuric acid, itself unstable with respect to ammonia and carbon dioxide. The best characterized organisms that use this pathway are of Pseudomonas sp. strain ADP.
  2. Dealkylation of the amino groups to give 2-chloro-4-hydroxy-6-amino-1,3,5-triazine, the degradation of which is unknown. This path also occurs in Pseudomonas species as well as a number of bacteria.[25][26]

Rates of biodegradation are affected by atrazine's low solubility, thus surfactants may increase the degradation rate. Though the two alkyl moieties readily support growth of certain microorganisms, the atrazine ring is a poor energy source due to the oxidized state of ring carbon. In fact, the most common pathway for atrazine degradation involves the intermediate, cyanuric acid, in which carbon is fully oxidized, thus the ring is primarily a nitrogen source for aerobic microorganisms. Atrazine may be catabolized as a carbon and nitrogen source in reducing environments, and some aerobic atrazine degraders have been shown to use the compound for growth under anoxia in the presence of nitrate as an electron acceptor,[27] a process referred to as a denitrification. When atrazine is used as a nitrogen source for bacterial growth, degradation may be regulated by the presence of alternative sources of nitrogen. In pure cultures of atrazine-degrading bacteria, as well as active soil communitites, atrazine ring nitrogen, but not carbon are assimilated into microbial biomass.[28] Low concentrations of glucose can decrease the bioavailability, whereas higher concentrations promote the catabolism of atrazine.[29]

The genes for enzymes AtzA-C have been found to be highly conserved in atrazine-degrading organisms worldwide. In Pseudomonas sp. ADP, the Atz genes are located noncontiguously on a plasmid with the genes for mercury catabolism. AtzA-C genes have also been found in a Gram-positive bacterium, but are chromosomally located.[30] The insertion elements flanking each gene suggest that they are involved in the assembly of this specialized catabolic pathway.[26] Two options exist for degradation of atrazine using microbes, bioaugmentation or biostimulation.[26] Recent research suggests that microbial adaptation to atrazine has occurred in some fields where the herbicide is used repetitively, resulting in more rapid biodegradation.[31] Like the herbicides trifluralin and alachlor, atrazine is susceptible to rapid transformation in the presence of reduced iron-bearing soil clays, such as ferruginous smectites. In natural environments, some iron-bearing minerals are reduced by specific bacteria in the absence of oxygen, thus the abiotic transformation of herbicides by reduced minerals is viewed as "microbially induced".[32]

Health and environmental effects

According to Extension Toxicology Network in the U.S., "The oral median Lethal Dose or LD50 for atrazine is 3090 mg/kg in rats, 1750 mg/kg in mice, 750 mg/kg in rabbits, and 1000 mg/kg in hamsters. The dermal LD50 in rabbits is 7500 mg/kg and greater than 3000 mg/kg in rats. The 1-hour inhalation LC50 is greater than 0.7 mg/L in rats. The 4-hour inhalation LC50 is 5.2 mg/L in rats." The maximum contaminant level is 0.003 mg/L and the reference dose is 0.035 mg/kg/day.[33]

Atrazine use in pounds per square mile by county. Atrazine is one of the most commonly used herbicides in the United States.[34]

Atrazine was banned in the European Union (EU) in 2004 because of its persistent groundwater contamination.[18]

Atrazine contamination of surface water (lakes, rivers, and streams) is monitored by EPA and has consistently exceeded levels of concern in 2 Missouri watersheds and 1 in Nebraska.[35] As of 2001, Atrazine was the most commonly detected pesticide in US drinking water.[4][5]: 2  Monitoring of atrazine levels in community water systems in 31 high use atrazine states found that atrazine levels exceeded levels of concern for infant exposure during at least one year between 1993-2001 in 34 of 3670 community water systems using surface water, and in none of 14,500 community water systems using groundwater.[36] Surface water monitoring data from 20 high atrazine use watersheds found peak atrazine levels of up to 147 parts per billion, with daily averages in all cases below 10 parts per billion.[37]

Mammals

In 2006 EPA stated that "the risks associated with the pesticide residues pose a reasonable certainty of no harm",[7][8] EPA opened a new review in 2009[9] that 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."[10]

In 2007 the U.S. EPA said that "studies thus far suggest that atrazine is an endocrine disruptor". The implications for children’s health are related to effects during pregnancy and during sexual development, though few studies are available. In people, risks for preterm delivery and intrauterine growth retardation have been associated with exposure. Atrazine exposure has been shown to result in delays or changes in pubertal development in female rats; conflicting results have been observed in males. Male rats exposed via milk from orally exposed mothers exhibited higher levels of prostate inflammation as adults; immune effects have also been seen in male rats exposed in utero or while nursing.[5]

A 2014 systematic review, funded by atrazine manufacturer Syngenta, assessed its relation to reproductive health problems. The authors concluded that the quality of most studies was poor and without good quality data the results were difficult to assess, though it was noted that no single category of negative pregnancy outcome was found consistently across studies. The authors concluded that a causal link between atrazine and adverse pregnancy outcomes was not warranted due to the poor quality of the data and the lack of robust findings across studies. Syngenta was not involved in the design, collection, management, analysis, or interpretation of the data and did not participation in the preparation of the manuscript.[38]

A 2011 review of the mammalian reproductive toxicology of atrazine jointly conducted by the World Health Organization and the Food and Agriculture Organization of the United Nations concluded that atrazine is not teratogenic. Reproductive effects in rats and rabbits were only seen at doses that were toxic to the mother. Observed adverse effects in rats included fetal resorption in rates (at doses > 50 mg/kg per day), delays in sexual development in female rats (at doses >30 mg/kg per day), and decreased birth weight (at doses >3.6 mg/kg per day).[39]

A Natural Resources Defense Council's Report said that the EPA is ignoring atrazine contamination in surface and drinking water in the central United States.[40]

Research results from the U.S. National Cancer Institute's 2011 Agricultural Health Study concluded that "there was no consistent evidence of an association between atrazine use and any cancer site." The study tracked 57,310 licensed pesticide applicators over 13 years.[41] EPA also determined in 2000 "that atrazine is not likely to cause cancer in humans."[42]

Amphibians

Atrazine is a suspected teratogen, with some studies reporting causing demasculinization in male northern leopard frogs even at low concentrations,[43][44] and an estrogen disruptor.[45] A 2002 study by Tyrone Hayes, of the University of California, Berkeley, found that exposure caused male tadpoles to turn into hermaphrodites – frogs with both male and female sexual characteristics.[46] An EPA review of this study concluded that overcrowding, questionable sample handling techniques and the failure of the authors to disclose key details including sample sizes, dose-response effects and the variability of observed effects made it difficult to assess the study's credibility and ecological relevance.[47] A 2005 Syngenta-funded study, requested by EPA and conducted under EPA guidance and inspection, was unable to reproduce these results.[48]

According to Hayes, all of the studies that rejected the hermaphroditism hypothesis were plagued by poor experimental controls and were funded by Syngenta, suggesting conflict of interest.[49] A recent EPA review article discussed the Hayes/Syngenta conflict to illustrate both financial and non-financial conflicts of interest. The authors concluded that "Statements by Hayes and Syngenta suggest that their scientific differences have developed a personal aspect that casts doubt on their scientific objectivity" and noted that "The inability of the scientific community to resolve this straightforward issue is an embarrassment." ([50]

EPA's Scientific Advisory Panel (SAP) examined all relevant studies and concluded that "atrazine does not adversely affect amphibian gonadal development based on a review of laboratory and field studies."[8] SAP made recommendations concerning proper study design for further investigation. As required by EPA, Syngenta conducted two experiments under Good Laboratory Practices (GLP) and inspection by EPA and German regulatory authorities. The paper concluded "These studies demonstrate that long-term exposure of larval X. laevis to atrazine at concentrations ranging from 0.01 to 100 microg/l does not affect growth, larval development, or sexual differentiation."[51] A 2008 report cited the independent work of researchers in Japan, who were unable to replicate Hayes' work. "The scientists found no hermaphrodite frogs; no increase in aromatase as measured by aromatase mRNA induction; and no increase in vitellogenin, another marker of feminization."[52]

A 2007 study examined the relative importance of environmentally relevant concentrations of atrazine on trematode cercariae versus tadpole defense against infection. Its principal finding was that susceptibility of wood frog tadpoles to infection by E. trivolvis is increased only when hosts were exposed to an atrazine concentration of 30 ng/L and not to 3 ng/L.[53]

A 2008 study reported that tadpoles developed deformed hearts and impaired kidneys and digestive systems when chronically exposed to atrazine concentrations of 10,000 ppb in their early stages of life. Tissue malformation may have been induced by ectopic programmed cell death, although a mechanism was not identified.[54]

A 2010 Hayes study concluded that atrazine rendered 75 percent of male frogs sterile and turned one in 10 into females.[55]

In 2010, the Australian Pesticides and Veterinary Medicines Authority (APVMA), tentatively concluded that environmental atrazine were not affecting amphibian populations in Australia:

The conclusion of the APVMA at that time, based on advice from DEWHA, was that atrazine is unlikely to have an adverse impact on frogs at existing levels of exposure. This advice was consistent with findings by the US EPA in 2007 (see below) that atrazine does not adversely affect amphibian gonadal development.[56]

Furthermore, the APVMA responded to Hayes' 2010 published paper,[57] by stating that his findings "do not provide sufficient evidence to justify a reconsideration of current regulations which are based on a very extensive dataset."[56]

Fish and insects

A 2004 study found no statistically significant reproductive effects in fathead minnow at atrazine levels up to 50 μg/L.[58] The study examined endpoints including survival, egg production, number of spawns, eggs/spawn, relative gonad weight, and gonad histology, among others. Trends were observed in relative testis weight, testis maturity, and percentage embryo fertilization in atrazine-exposed fish, the but were not statistically significant. In contrast, in fish exposed to estradiol at 0.5 ug/mL as a positive control all endpoints were significantly different from atrazine-exposed fish and control fish. The authors concluded that atrazine does not have strong estrogenic effects in adult fathead minnows or cause overt reproductive toxicity at environmentally relevant concentrations

A 2010 study conducted by scientists from the U.S. Geological Survey observed substantial adverse reproductive effects on fish from atrazine exposure at a threshold concentration of 0.5 μg/L, which is below the threshold levels previously defined for fish toxicity and within the surface water concentrations found in agricultural areas; the authors concluded: "The effects on egg production and spawning in fathead minnow suggest the reproductive risks of atrazine exposure to feral fish populations in high use, agricultural areas may be under estimated by current evaluations."[11] A 2014 study found similar results in Japanese medaka fish.[59]

Class action lawsuit

In 2012 Syngenta corporation, manufacturer of atrazine, was the defendant in a class action lawsuit concerning the levels of atrazine in human water supplies. Syngenta agreed to pay $105 million to reimburse more than one thousand water systems for "the cost of filtering atrazine from drinking water". The company denied all wrongdoing.[2] [60][61]

See also

References

  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 d e "A Valuable Reputation: Tyrone Hayes said that a chemical was harmful, its maker pursued him" by Rachel Aviv, The New Yorker, 10 February 2014
  3. ^ a b c "Chemical Review: Atrazine". Australian Pesticides and Veterinary Medicines Authority. Retrieved 2015-02-11.
  4. ^ a b 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 March 2006, Revised February 15, 2007
  5. ^ a b c d e f Atrazine: Chemical Summary. Toxicity and Exposure Assessment for Children’s Health (PDF) (Report). U.S. Environmental Protection Agency. 2007-04-24.
  6. ^ a b Hayes, Tyrone B. (2011). "Demasculinization and feminization of male gonads by atrazine: Consistent effects across vertebrate classes". The Journal of Steroid Biochemistry and Molecular Biology. 127 (1–2): 64–73. doi:10.1016/j.jsbmb.2011.03.015. PMID 21419222. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  7. ^ a b Triazine Cumulative Risk Assessment and Atrazine, Simazine, and Propazine Decisions, June 22, 2006, EPA.
  8. ^ a b c Atrazine Updates: Amphibians, April 2010, EPA.
  9. ^ a b EPA Begins New Scientific Evaluation of Atrazine, October 7, 2009, EPA.
  10. ^ a b EPA Atrazine Updates: Scientific Peer Review—Human Health Current as of January 2013. Accessed March 15, 2014
  11. ^ a b Tillitt; et al. (Aug 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. {{cite journal}}: Explicit use of et al. in: |last2= (help)
  12. ^ Duhigg, Charles (August 22, 2009). "Debating How Much Weed Killer Is Safe in Your Water Glass". The New York Times. Retrieved 2009-09-10.
  13. ^ Walsh, Edward (2003-02-01). "EPA Stops Short of Banning Herbicide". Washington Post. pp. A14. Retrieved 2007-04-27.
  14. ^ "Restricted Use Products (RUP) Report: Six Month Summary List". Environmental Protection Agency. Archived from the original on 11 January 2010. Retrieved 1 December 2009. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  15. ^ Danny Hakimfeb for the New York Times. February 23, 2015. A Pesticide Banned, or Not, Underscores Trans-Atlantic Trade Sensitivities
  16. ^ European Commission Health & Consumer Protection Directorate-General Directorate E – Food Safety: plant health, animal health and welfare, international questions E1 - Plant health. 3 October 2003 Review report for the active substance atrazine Finalised in the Standing Committee on the Food Chain and Animal Health
  17. ^ European Chemicals Agency Database: Atrazine Page accessed April 19, 2015
  18. ^ a b Ackerman, Frank (2007). "The economics of atrazine" (PDF). International Journal of Occupational and Environmental Health. 13 (4): 437–445. doi:10.1179/oeh.2007.13.4.437. PMID 18085057.
  19. ^ "BioOne Online Journals - A Rationale for Atrazine Stewardship in Corn".
  20. ^ Fawcett, Richard S. "Twenty Years of University Corn Yield Data: With and Without Atrazine", North Central Weed Science Society, 2008
  21. ^ "Market-level assessment of the economic benefits of atrazine in the United States - Mitchell - 2014 - Pest Management Science - Wiley Online Library".
  22. ^ Wolfgang Krämer (2007). Modern Crop Protection Compounds, Volume 1. Wiley-VCH. ISBN 9783527314966.
  23. ^ Appleby, Arnold P.; Müller, Franz; Carpy, Serge (2001). "Ullmann's Encyclopedia of Industrial Chemistry". doi:10.1002/14356007.a28_165. ISBN 3-527-30673-0. {{cite journal}}: |chapter= ignored (help); Cite journal requires |journal= (help)
  24. ^ Interim Reregistration Eligibility Decision for Atrazine, U.S. EPA, January, 2003.
  25. ^ Zeng Y, Sweeney CL, Stephens S, Kotharu P. (2004). Atrazine Pathway Map. Wackett LP. Biodegredation Database.
  26. ^ a b c Wackett, L. P.; Sadowsky, M. J.; Martinez, B.; Shapir, N. (January 2002). "Biodegradation of atrazine and related s-triazine compounds: from enzymes to field studies". Applied Microbiology and Biotechnology. 58 (1): 39–45. doi:10.1007/s00253-001-0862-y. PMID 11831474.
  27. ^ Crawford, J. J., G.K. Sims, R.L. Mulvaney, and M. Radosevich (1998). "Biodegradation of atrazine under denitrifying conditions". Appl. Microbiol. Biotechnol. 49 (5): 618–623. doi:10.1007/s002530051223. PMID 9650260.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  28. ^ Bichat, F., G.K. Sims, and R.L. Mulvaney (1999). "Microbial utilization of heterocyclic nitrogen from atrazine". Soil Science Society of America Journal. 63: 100–110. doi:10.2136/sssaj1999.03615995006300010016x.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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  30. ^ Cai B, Han Y, Liu B, Ren Y, Jiang S. (2003). "Isolation and characterization of an atrazine-degrading bacterium from industrial wastewater in China". Letters in Applied Microbiology. 36 (5): 272–276. doi:10.1046/j.1472-765X.2003.01307.x. PMID 12680937.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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