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									Atrazine
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                 Atrazine




              1-chloro-3-ethylamino-5-
  IUPAC
              isopropylamino-2,4,6-
  name
              triazine

  Other       Atrazine
  names       See also synonyms

                Identifiers

  CAS
              1912-24-9
  number

               [show]
  SMILES


                Properties

  Molecular C8H14ClN5
  formula

  Molar mass 215.68 g mol−1

  Appearance colorless solid

  Density       1.187 g/cm³

  Melting
  point         175 °C (448 K)

  Boiling
             200 °C (473 K)
  point
  Solubility
             0.007 g/100 mL (?°C)
  in water
  Except where noted otherwise, data are given
                       for
        materials in their standard state
              (at 25 °C, 100 kPa)
              Infobox references



Atrazine, 2-chloro-4-(ethylamine)-6-(isopropylamine)-s-triazine, an organic compound
consisting of an s-triazine-ring is a widely used herbicide. Its use is controversial due to its
effects on nontarget species, such as on amphibians.[1] Like many commercial products, it is sold
under numerous trade names. Its use is banned in the European Union but is still one of the most
widely used herbicides in the U.S. with 77 million lb applied in 2003.

Contents
[hide]

        1 Uses
        2 Biodegradation
        3 Controversy
        4 Toxicity
        5 References
        6 Further reading



[edit] Uses
Atrazine is used to stop pre- and post-emergence broadleaf and grassy weeds in major crops by
binding to the plastoquinone-binding protein in photosystem II, inhibiting electron transport.
Atrazine and its derivatives are also used in many industrial processes, including the production
of some dyes and explosives.[citation needed] Atrazine is the most widely used herbicide in
conservation tillage systems, which are designed to prevent soil erosion.

Its effect on yields has been estimated from 6% to 1%, with 3-4% being the conclusion of an
extensive review.[2]

[edit] Biodegradation
The half-life of atrazine in soil is 13 to 261 days.[3] Atrazine biodegradation can occur by two
known pathways:

1) Atrazine can be dechlorinated followed by removal the other ring substituents via
amidohydrolases by the enzymes AtzA, AtzB, and AtzC. The end product is cyanuric acid. The
best characterized organism that performs this pathway is Pseudomonas sp. strain ADP.

2) The other pathway involves dealkylation of the amino groups. Subsequent dechlorination
yields cyanuric acid. The end result is 2-chloro-4-hydroxy-6-amino-1,3,5-triazine, which
currently has no known path to further degradation. This path occurs in Pseudomonas species
and a number of bacteria.[4][5]

Atrazine degrades in soil by the action of microbes. Rates of biodegradation are affected by
atrazine's low solubility, thus surfactants increase the degradation rate. Atrazine itself is a poor
energy source due to the highly oxidized carbons in the ring. It is catabolized as a carbon and
nitrogen source in reducing environments. Inorganic nitrogen accelerates atrazine catabolism
whereas organic nitrogen decreases it. Low concentrations of glucose can decrease the
bioavailability, whereas higher concentrations promote the catabolism of atrazine.[6]

The genes for enzymes AtzA-C have been found to be highly conserved in atrazine-degrading
organisms worldwide. The prevalence of these genes could be due to the mass transfer of AtzA-
C on a global scale. In Pseudomonas sp. ADP, the Atz genes are located non-contiguously on a
plasmid with the genes for mercury catabolism. This plasmid is conjugatable to Gram negative
bacteria in the laboratory and could lead to the worldwide distribution, in view of the extensive
release of atrazine and mercury. AtzA-C have also been found in a Gram positive bacterium but
are chromosomally located.[7] The insertion elements flanking each gene suggests that they are
involved in the assembly of this specialized catabolic pathway.[5] Two options exist for
degradation of atrazine using microbes: bioaugmentation or biostimulation.[5]

[edit] Controversy
           It has been suggested that this article be split into articles entitled Atrazine
          controversy, accessible from a disambiguation page. (Discuss)




Atrazine use in pounds per square mile by county. Atrazine is one of the most commonly used
herbicides in the United States.[8]

Atrazine was banned in the European Union (EU) in 2004 because of its persistent groundwater
contamination[2] In the United States, however, atrazine is one of the most widely used
herbicides, with 76 million pounds of it applied each year.[9] It is probably the most commonly
used herbicide in the world, and is used in about 80 countries worldwide.[10] Its endocrine effects,
possible carcinogenic effect, and epidemiological connection to low sperm levels in men has led
several researchers to call for banning it in the US.[2]

Tyrone Hayes, a scientist at UC Berkeley, found evidence that it is a teratogen, causing
demasculinization in male frogs even at low concentrations,[11] and an estrogen disruptor.[12]
Male frogs affected by atrazine could reach testosterone levels below females.[10] However, at
least one study [13], was unable to reproduce the results.

The U.S. Environmental Protection Agency (EPA) and its independent Scientific Advisory Panel
(SAP) examined all available studies on this topic — including Hayes' work — and concluded
that there is "currently insufficient data" to determine if atrazine affects amphibian development.
Hayes, formerly part of the SAP panel, resigned in 2000 to continue studies independently.[14]
Hayes notes that all of the studies that failed to conclude that atrazine caused hermaphroditism
were plagued by poor experimental controls and were funded by Syngenta, the company that
produces the chemical.[15] In 2006 the U.S. EPA considered re-registration of Atrazine final
when it issued a cumulative risk assessments on the triazine herbicides, and concluded that they
posed "no harm that would result to the general U.S. population, infants, children or
other...consumers."[16] A former scientist working for the Minnesota Pollution Control Agency
believes he was fired for attempting to testify against atrazine.[17]

In a Tufts University study published in February 2008 it was reported that young tadpoles
undergoing organ morphogenesis were found to develop deformed hearts and impaired kidneys
and digestive systems when exposed to atrazine. Tissue malformation may be induced by ectopic
programmed cell death, although a mechanism was not identified.[18]

[edit] Toxicity
According to Extension Toxicology Network, "The oral 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." [19]

[edit] References
   1. ^ Jennifer Lee (2003-06-19). "Popular Pesticide Faulted for Frogs' Sexual
       Abnormalities", The New York Times.
   2. ^ a b c Frank Ackerman. (2007). [ase.tufts.edu/gdae/Pubs/rp/EconAtrazine.pdf The
       Economics of Atrazine]. Int J Occup Environ Health].
   3. ^ Interim Reregistration Eligibility Decision for Atrazine, U.S. EPA, January, 2003.
   4. ^ Zeng Y, Sweeney CL, Stephens S, Kotharu P. (2004). Atrazine Pathway Map. Wackett
       LP. Biodegredation Database.
   5. ^ a b c Wackett LP, Sadowsky MJ, Martinez B, Shapir N (January 2002). "Biodegradation
       of atrazine and related s-triazine compounds: from enzymes to field studies". Appl.
       Microbiol. Biotechnol. 58 (1): 39–45. doi:10.1007/s00253-001-0862-y. PMID 11831474.
   6. ^ Ralebitso TK, Senior E, van Verseveld HW (2002). "Microbial aspects of atrazine
       degradation in natural environments". Biodegradation 13: 11–19.
       doi:10.1023/A:1016329628618.
   7. ^ 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: 272–276. doi:10.1046/j.1472-765X.2003.01307.x.
   8. ^ USGS Pesticide Use Maps
   9. ^ Walsh, Edward (2003-02-01). "EPA Stops Short of Banning Herbicide", Washington
       Post, pp. A14. Retrieved on 27 April 2007.
   10. ^ a b Briggs H. (April 15, 2002), Pesticide 'causes frogs to change sex'. BBC News.
       Retrieved on 2007-10-16.
   11. ^ Tyrone Hayes, Kelly Haston, Mable Tsui, Anhthu Hoang, Cathryn Haeffele, and Aaron
       Vonk (2003). "Atrazine-Induced Hermaphroditism at 0.1 ppb in American Leopard
       Frogs" (Free full text). Environmental Health Perspectives 111. doi:10.1289/ehp.5932.
       http://www.ehponline.org/members/2003/5932/5932.html.
   12. ^ Mizota, K.; Ueda, H. (2006). "Endocrine Disrupting Chemical Atrazine Causes
       Degranulation through Gq/11 Protein-Coupled Neurosteroid Receptor in Mast Cells".
       Toxicological Sciences 90: 362. doi:10.1093/toxsci/kfj087. PMID 16381660.
       http://toxsci.oxfordjournals.org/cgi/content/full/90/2/362#BDY.
   13. ^ Jooste et al., 2005 Gonadal Development of Larval Male Xenopus laevis Exposed to
       Atrazine in Outdoor Microcosms Environ. Sci. Technol. 39, 5255-5261
   14. ^ Weedkiller 'threatens frogs', BBC News
   15. ^ Hayes, TB (2004). "There Is No Denying This: Defusing the Confusion about
       Atrazine". Bioscience 54 (112): 1138–1149. doi:10.1641/0006-
       3568(2004)054[1138:TINDTD]2.0.CO;2.
   16. ^ Triazine Cumulative Risk Assessment and Atrazine, Simazine, and Propazine
       Decisions, June 22, 2006, EPA.
   17. ^ Davidson C. (2007). Whistleblower Wotzka, legislators and researcher put Atrazine
       back in spotlight. Twin Cities Daily Planet.
   18. ^ Early Exposure To Common Weed Killer Impairs Amphibian Development
   19. ^ Pesticide Information Profile: Atrazine, Extension Toxicology Network (Cooperative
       Extension Offices of Cornell University, Oregon State University, the University of
       Idaho, and the University of California at Davis and the Institute for Environmental
       Toxicology, Michigan State University), June 1996.

[edit] Further reading
       Fan W, Yanase T, Morinaga H, et al (May 2007). "Atrazine-induced aromatase
        expression is SF-1 dependent: implications for endocrine disruption in wildlife and
        reproductive cancers in humans". Environ. Health Perspect. 115 (5): 720–7.
        doi:10.1289/ehp.9758. PMID 17520059.
       Tyrone Hayes' page about his research on Atrazine: atrazinelovers.com
       Synonyms and brand names

                                              [hide]
v•d•e
                                           Herbicides

                  acetochlor · alachlor · asulam · butachlor · diethatyl · diflufenican ·
Anilides/Anilines dimethenamid · flamprop · metazachlor · metolachlor · pendimethalin ·
                  pretilachlor · propachlor · propanil · trifluralin

                    aminopyralid · chloramben · clopyralid · dicamba · picloram · pyrithiobac ·
Aromatic acids
                    quinclorac · quinmerac

Arsenicals          cacodylic acid · copper arsenate · DSMA · MSMA

Organophosphorus bensulide · bilanafos · ethephon · fosamine · glufosinate · glyphosate ·
             piperophos

Phenoxy      2,4-D · 2,4-DB · dichlorprop · fenoprop · MCPA · MCPB · 2,4,5-T

Pyridines    dithiopyr · fluroxypyr · imazapyr · thiazopyr · triclopyr

Quaternary   diquat · MPP · paraquat

             ametryn · atrazine · cyanazine · hexazinone · prometon · prometryn ·
Triazines
             propazine · simazine · simetryn · terbuthylazine · terbutryn

Ureas        chlortoluron · DCMU · metsulfuron-methyl

             3-AT · bromoxynil · clomazone · DCBN · dinoseb · juglone · methazole ·
Others
             metham sodium · sulfentrazone

								
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