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Atrazine

From Wikipedia, the free encyclopedia
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 100.016.017Edit 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-NcheckY
  • 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 215.69g·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 theirstandard state(at 25 °C [77 °F], 100 kPa).

Atrazineis achlorinatedherbicideof thetriazineclass.[2]It is used to prevent pre-emergence broadleafweedsin crops such asmaize(corn),[3]soybean[3]andsugarcaneand on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer isSyngentaand 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 theEuropean Unionin 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 anendocrine disruptor,an agent that can alter the natural hormonal system.[9]However, in 2006 theU.S. Environmental Protection Agency(EPA) had stated that under theFood 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]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]

Uses

[edit]

Atrazine is aherbicidethat is used to stop pre- and post-emergence broadleaf and grassyweedsin crops such assorghum,maize,sugarcane,lupins,pine,andeucalyptplantations, and triazine-tolerantcanola.[5]

In theUnited Statesas of 2014, atrazine was the second-most widely used herbicide afterglyphosate,[16]with 76 million pounds (34 thousand metric tons) of it applied each year.[19][20]Atrazine continues to be one of the most widely used herbicides in Australian agriculture.[5]Its effect on corn yields has been estimated from 1% to 8%, with 3–4% being the conclusion of one economics review.[21][22]In another study looking at combined data from 236 university corn field trials from 1986 to 2005, atrazine treatments showed an average increase of 5.7 US bushels per acre (0.50 m3/ha) (~400 kilograms per hectare (360 lb/acre)) than alternative herbicide treatments.[23]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.[24]

Several teams havenanoencapsulatedthis herbicide to enhance usability.[25]Most notably Takeshitaet al.,2021, Oliveiraet al.2015,, Preisleret al.,2019 and Bragançaet al.,2023 improve atrazine'sefficacywithnanoparticlecombinations in field usage.[25]

Chemistry and biochemistry

[edit]

Atrazine was invented in 1958 in theGeigylaboratories as the second of a series of1,3,5-triazines.[26]

Atrazine is prepared fromcyanuric chloride,which is treated sequentially withethylamineandisopropylamine.Like other triazine herbicides, atrazine functions by binding to theplastoquinone-bindingproteininphotosystem II,which animals lack. Plant death results from starvation and oxidative damage caused by breakdown in theelectron transportprocess. Oxidative damage is accelerated at high light intensity.[27]

Atrazine's effects in humans and animals primarily involve theendocrine system.Studies suggest that atrazine is anendocrine disruptorthat can causehormone imbalance.[9]

Atrazine has been found to act as anagonistof theG protein-coupled estrogen receptor 1.[28]Atrazine has been shown to bind covalently to (chemically react with) a large number of mammalian proteins.[29]

Environment

[edit]

Levels

[edit]

Atrazine contamination of surface water (lakes, rivers, and streams) in the U.S. has been monitored by the EPA and has consistently exceeded levels of concern in two Missouri watersheds and one in Nebraska.[30]Monitoring of atrazine levels in community water systems in 31 high-use states found that levels exceeded levels of concern for infant exposure during at least one year between 1993 and 2001 in 34 of 3670 community water systems using surface water, and in none of 14,500 community water systems using groundwater.[31]Surface water monitoring data from 20 high atrazine use watersheds found peak atrazine levels up to 147 parts per billion, with daily averages in all cases below 10 parts per billion.

Biodegradation

[edit]
Biodegradation - atrazine chlorohydrolase pathway
Atrazine chlorohydrolasepathway

Atrazine remains in soil for a matter of months (although in some soils can persist to at least four years)[9]and can migrate from soil togroundwater;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 U.S. Environmental Protection Agency expresses concern regarding contamination of surface waters (lakes, rivers, and streams).[9]

Atrazine degrades insoilprimarily by the action ofmicrobes.Thehalf-lifeof atrazine in soil ranges from 13 to 261 days.[32]Atrazinebiodegradationcan occur by two known pathways:

  1. Hydrolysisof the C-Cl bond is followed by theethylandisopropylgroups, catalyzed by thehydrolaseenzymescalled AtzA, AtzB, and AtzC. The end product of this process iscyanuric acid,itself unstable with respect to ammonia and carbon dioxide. The best characterized organisms that use this pathway are ofPseudomonassp. strain ADP.
  2. Dealkylation of theamino groupsgives 2-chloro-4-hydroxy-6-amino-1,3,5-triazine, the degradation of which is unknown. This path also occurs inPseudomonasspecies, as well as a number of bacteria.[33][34]

Rates of biodegradation are affected by atrazine's low solubility; thussurfactantsmay 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 becatabolizedas 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,[35]a process referred to as adenitrification.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 communities, atrazine ring nitrogen, but not carbon are assimilated into microbial biomass.[36]Low concentrations ofglucosecan decrease the bioavailability, whereas higher concentrations promote the catabolism of atrazine.[37]

Thegenesfor enzymesAtzA-C have been found to be highly conserved in atrazine-degrading organisms worldwide. InPseudomonassp. ADP[clarification needed],the Atz genes are located noncontiguously on aplasmidwith the genes formercurycatabolism. AtzA-C genes have also been found in aGram-positive bacterium,but are chromosomally located.[38]The insertion elements flanking each gene suggest that they are involved in the assembly of this specialized catabolic pathway.[34]Two options exist for degradation of atrazine using microbes,bioaugmentationorbiostimulation.[34]Like the herbicidestrifluralinandalachlor,atrazine is susceptible to rapid transformation in the presence of reduced iron-bearing soil clays, such as ferruginoussmectites.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".[39]

Photolysis

[edit]

In 2016, photolytic degradation with 254 nmultravioletwas seen by the authors of a particular study as an efficient process, which could be used in pilot plants to reduce or eliminate compounds of the atrazine class or similar emerging contaminants, in effluents.[40]

Toxicology

[edit]

According to Extension Toxicology Network in the U.S., "The oral median Lethal Dose orLD50for atrazine is 3090 mg/kg inrats,1750 mg/kg inmice,750 mg/kg inrabbits,and 1000 mg/kg in hamsters. The dermal LD50in rabbits is 7500 mg/kg and greater than 3000 mg/kg in rats. The 1-hour inhalation LC50is greater than 0.7 mg/L in rats. The 4-hour inhalation LC50is 5.2 mg/L in rats. "Themaximum contaminant levelis 0.003 mg/L and thereference doseis 0.035 mg/kg/day.[41]

Atrazine use in the USA in 2019

Mammals

[edit]

A September 2003 review by theAgency for Toxic Substances and Disease Registry(ATSDR) stated that atrazine is "currently under review for pesticide re-registration by the EPA because of concerns that atrazine may cause cancer", but not enough information was available to "definitely state whether it causes cancer in humans." According to the ATSDR, one of the primary ways that atrazine can affect a person's health is "by altering the way that the reproductive system works. Studies of couples living on farms that use atrazine for weed control found an increase in the risk of preterm delivery, but these studies are difficult to interpret because most of the farmers were men who may have been exposed to several types of pesticides. Little information is available regarding the risks to children, however" [m]aternal exposure to atrazine in drinking water has been associated with low fetal weight and heart, urinary, and limb defects in humans ".[42]Incidence of a birth defect known asgastroschisisappears to be higher in areas where surface water atrazine levels are elevated especially when conception occurs in the spring, the time when atrazine is commonly applied.[43]

TheWorld Health Organization'sInternational Agency for Research on Cancerhas classified atrazine as "not classifiable as to its carcinogenicity to humans" (Group 3).[44]

The EPA determined in 2003 "that atrazine is not likely to cause cancer in humans".[45]

In 2006, the EPA stated, "the risks associated with the pesticide residues pose a reasonable certainty of no harm".[10][11]

In 2007, the EPA said, "studies thus far suggest that atrazine is anendocrine 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 inpubertaldevelopment 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.[9]EPA opened a new review in 2009[12]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."[13]Deborah A. Cory-Slechta, a professor at the University of Rochester in New York has said in 2014, "The way the E.P.A. tests chemicals can vastly underestimate risks." She has studied atrazine's effects on the brain and serves on the E.P.A.'s science advisory board. She further stated, "There's still a huge amount we don't know about atrazine."[16]

ANatural Resources Defense Councilreport from 2009 said that the EPA is ignoring atrazine contamination in surface and drinking water in the central United States.[46]

"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.[47]

A 2011 review of the mammalian reproductive toxicology of atrazine jointly conducted by theWorld Health Organizationand theFood and Agriculture Organizationof the United Nations concluded that atrazine was notteratogenic.Reproductive effects in rats and rabbits were only seen at doses that were toxic to the mother. Observed adverse effects in rats includedfetal resorptionin 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).[48]

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 participate in the preparation of the manuscript.[49]

Amphibians

[edit]

Atrazine has been a suspectedteratogen,with some studies reporting causing demasculinization in malenorthern leopard frogseven at low concentrations.[50]A 2002 study byTyrone Hayes,of the University of California, Berkeley, found that exposure caused maletadpolesto turn intohermaphrodites– frogs with both male and female sexual characteristics.[51][52]However, this study has not been able to bereplicated,[53]and a 2003 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.[53][54]A 2005 study, requested by EPA and conducted under EPA guidance and inspection, was unable to reproduce Hayes' results.[55]

In 2010, theAustralian Pesticides and Veterinary Medicines Authority(APVMA) tentatively concluded that environmental atrazine "at existing levels of exposure" was not affecting amphibian populations in Australia consistent with the 2007 EPA findings.[56]APVMA responded to Hayes' 2010 published paper,[57]that his findings "do not provide sufficient evidence to justify a reconsideration of current regulations which are based on a very extensive dataset."[56] The EPA's Scientific Advisory Panel examined relevant studies and concluded in 2010, "atrazine does not adversely affect amphibian gonadal development based on a review of laboratory and field studies".[11]It recommended proper study design for further investigation. As required by the EPA, two experiments were conducted under Good Laboratory Practices (GLP) and were inspected by EPA and German regulatory authorities, concluding 2009 that "long-term exposure of larvalX. laevisto atrazine at concentrations ranging from 0.01 to 100 μg/L does not affect growth, larval development, or sexual differentiation ".[58]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 invitellogenin,another marker of feminization. "[59] The Atrazine Saga has been chronicled.[60]

2012 Class action lawsuit

[edit]

In 2012, Syngenta, 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.[16][61][62]

2015 Canadian regulatory review

[edit]

Prompted by the EU's 2004 ban, a regulatory review of the product in Canada by thePMRAwas begun in 2015. On 31 March 2017 the review result was published and the PMRA decided to leave unchanged the product's registration. This was done because while the EU's ban was based on a legislated pollutant level of 0.1 μg/L, the Canadian regulations call for a home-grown "risk-based scientific approachin determining the risk to human health from pesticides in drinking water. "The US drinking water standard of 3 μg/L is approximately the same to the Canadian standard of 5 μg/L. Both maximum pollutant levels in North America were not exceeded by the maximum pollutant level in Canadian data of 2.32 μg/L.[63]

See also

[edit]

References

[edit]
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[edit]
  • Atrazine- PubChem(National library of medicine) - atrazine
  • Atrazine Fact Sheet- National Pesticide Information Center - Atrazine Fact Sheet
  • Atrazine- CDC - NIOSH Pocket Guide to Chemical Hazards
  • Atrazinein the Pesticide Properties DataBase (PPDB)
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