Atrazine
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| Atrazine | |
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| General | |
| Systematic name | 1-Chloro-3-ethylamino-5-isopropylamino-2,4,6-triazine |
| Other names | 2-Chloro-4-(2-propylamino)-6-ethylamino-s-triazine; 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine; 2-chloro-4-ethylamino-6-isopropylamino-s-triazine; 2-Chloro-4-(isopropylamino)-6-ethylamino-s-triazine; Ortho St. Augustine Weed and Feed; 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine; A 361; aatrex; AAtrex 4L; AAtrex 80W; aatrex nine-o; actinite pk; akticon; aktikon; aktikon pk; aktinit a; aktinit pk; argezin; atazinax; Atranex; atrasine; atrataf; Atratol; atratol a; Atrazine; Atrazine 4L; Atrazine 80W; Atrazine ; Atrazines; ATRAZINE (PRIMATOL); Atred; Atrex; Attrex; ATZ; Azinotox 500; Candex; cekuzina-t; chromozin; Crisamina; crisatrina; crisazine; Crisazina; Cyazine; Extrazine II; farmco atrazine; fenamine; Fenatrol; Fogard; g 30027; geigy 30,027; gesaprim; gesaprim 50; gesaprim 500; gesoprim; Griffex; Griffex 4L; hungazin; hungazin pk; inakor; Laddock; maizina; Mebazine; oleogesaprim; oleogesaprim 200; pitezin; primatol; Primatol A; primaze; radizine; Radazine; Scotts Bonus Type S; strazine; triazine a 1294; Vectal; Vectal SC; Vectral SC; Weedex; weedex a; Wonuk; zeaphos; zeapos; zeazin |
| Molecular formula | C8H14ClN5sub |
| SMILES | ClC1=NC(NC(C)C) =NC(NCC)=N1 |
| Molar mass | 215.685 g/mol |
| Appearance | Solid, colorless crystal |
| CAS number | [1912-24-9] |
| Properties | |
| Density and phase | 1.187 g/cm3, ? |
| Solubility in water | .007 g/100 ml (?°C) |
| Melting point | 175°C (? K) |
| Boiling point | 200°C (? K) |
| Acidity (pKa) | ? |
| Basicity (pKb) | ? |
| Chiral rotation [α]D | ?° |
| Viscosity | ? cP at ?°C |
| Structure | |
| Molecular shape | ? |
| Coordination geometry |
? |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ?°C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Other anions | ? |
| Other cations | ? |
| Related ? | ? |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
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Atrazine, 2-chloro-4-(ethylamine)-6-(isopropylamine)-s-triazine, is a s-triazine-ring herbicide that is used globally to stop pre and post emergence broadleaf and grassy weeds in major crops. Atrazine binds to the plastoquinone-binding protein in photosystem II, inhibiting electron transport. Atrazine is one of the most widely used herbicides and according to the Environmental Protection Agency (EPA) the U.S. used 77 million lb of Atrazine in 2003. In 2003, EPA classified the herbicide as "not likely" to cause cancer in humans, stating it did "not find any results among the available studies that would lead us to conclude that a potential cancer risk is likely from exposure to atrazine." After a 10-year science review, EPA recommended atrazine's re-registration in October 2003. A final re-registration decision is expected in late 2006. The half-life of atrazine in soil is 15 to 100 days. Atrazine and its derivatives are used in many industrial processes as well, including use in dyes and explosives. Hydroxyatrazine is unregulated and no negative effect is known. However, atrazine is the most widely used herbicide in conservation tillage systems, which means it helps prevent soil erosion and runoff by as much as 90 percent.
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.
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[edit] Biodegradation
The start of atrazine biodegradation can occur by three known ways. Atrazine can be dechlorinated and then the other ring substituents are removed by amidohydrolases. These steps are performed by AtzA-C respectively, which are commonly produced by a single organism. The end product, cyanuric acid, is then used as a carbon and nitrogen source. The most characterized organism that performs this pathway is Pseudomonas sp. ADP. The other mechanism involves dealkylation of the amino groups. In this mechanism dechlorination can be performed in the second step to eventually yield cyanuric acid, or 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 can occur by a single Pseudomonas species or by a number of bacteria (Zeng Y, et al) (Wackett LP, et al).
Sorption of atrazine in soil determines the bioavailability to degradation, which is performed mostly by microbes. Low atrazine biodegradation rates are a product of low solubility and sorption to areas inaccessible by bacteria. The addition of surfactants increases the solubility, increasing catalysis. Before use the surfactant must be evaluated for its effect on the environment as well as its use as a preferential carbon and energy source must be evaluated. 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 limiting environments although the optimum carbon and nitrogen availability is not known. It has been shown that inorganic nitrogen increases atrazine catabolism while organic nitrogen decreases it. Low concentrations of glucose can have the effect of decreasing bioavailability though formation of bound atrazine, while higher concentrations promote the catabolism of atrazine (Ralebitso TK, et al).
The genes AtzA-C have been found to be highly conserved in atrazine degrading organisms worldwide. This 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 mercury catabolism genes as well. This plasmid is conjugatable to Gram negative bacteria in the lab and could easily lead to the worldwide distribution with the amount of atrazine and mercury being produced. AtzA-C have also been found in a Gram positive bacterium, but chromosomally located (Cai B, et al). This is not surprising due to the presence of insertion elements flanking each gene and the detection of these genes on different plasmids. Their configurations on these different plasmids suggest the insertion elements are involved in the assembly of this specialized catabolic pathway (Wackett LP, et al). Two options exist for degradation of atrazine using microbes: bioaugmentation or biostimulation (Wackett LP, et al).
[edit] Controversy
UC Berkeley Professor Tyrone Hayes, James Carr at Texas Tech University and two other laboratories, found that even in very small levels atrazine was an endocrine disruptor. Syngenta. EPA and its independent Scientific Advisory Panel (SAP) examined all available studies on this topic - including Hayes' work - and concluded there is "currently insufficient data" to determine if atrazine may affect amphibian development. Hayes ,formerly part of the panel, resigned in 2000 to continue studies independently. [1]. A survey of animals in the wild has been published in the journal Nature. [2]
[edit] References
- Cai B, Han Y, Liu B, Ren Y, Jiang S. (2003). Isolation and characterization of an atrazine-degrading bacteriam from inductral wastewater in China. Lett Appl Microbiol. 36:272-276.
- Ralebitso TK, Senior E, van Verseveld HW. (2002). Microbial aspects of atrazine degradation in natural environments. B iodegradation. 13:11-19.
- Wackett LP, Sadowsky MJ, Martinez B. (2002). Biodegradation of atraxine and related s-triazine compounds: from enzymes to field studies. Appl Microbiol Biotechnol. 58:39-45.
- Zeng Y, Sweeney CL, Stephens S, Kotharu P. (2004). Atrazine Pathway Map. Wackett LP. Biodegredation Database. Online.
- http://umbbd.ahc.umn.edu/atr/atr_map.html
