Chemical, biochemical and environmental aspects of atrazine

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Research Paper 01/11/2014
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Chemical, biochemical and environmental aspects of atrazine

Vijay Kumar, Virender Kumar, Niraj Upadhyay, Sitansh Sharma
J. Bio. Env. Sci.5( 5), 149-165, November 2014.
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Atrazine herbicide is one of the primarily herbicide used for agricultural purposes worldwide. Amongst the different herbicide used more attention is paid to atrazine as it exhibit serious environmental problems including ecological risks and some human health damages. Due to their extensive usage and long half life period most of the actual evidence suggests that atrazine herbicide is omnipresent compounds found in different ecological compartments. Their highly hydrophilic character and low volatility have resulted in significant persistence in the aquatic environment. Very few studies describe the detailed study on fate and toxicity of atrazine herbicide in the environment. Here we review several important issues with regard to: (1) Laboratory based synthesis and mode of action on plant (2) the toxicity of atrazine herbicide (3) methods for determination in different biological systems and; (5) the by-products generated during chemical and biological decomposition. Based on recent research results the occurrence of atrazine herbicide in the environment inhibits the growth of some terrestrial aquatic species and leads to environmental risks. Most of the wastewater treatment plants are not capable of removing effectively the atrazine herbicide. Therefore there is a need to develop alternative processes to remove them from waters. Advanced oxidation processes have been proposed as alternative methods to ensure higher degradation and mineralization of atrazine herbicide are present in waters. Based on recent research results in the different biological media mass chromatography is considered as best tool for the determination of atrazine.


Acosta EJ, Steffensen MB, Tichy SE, Simanek EE. 2004. Removal of atrazine from water using covalent sequestration. Journal of Agriculture and Food Chemistry 52(3), 545-549.

Ahalya  N,  Ramchandra  TV,  Kanamadi  RD. 2003. Biosorption of Heavy Metals. Research Journal of Chemistry and Environment 7(4), 71-74.

Anipsitakis GP, Dionysiou DD. 2003. Degradation of organic contaminants in water with sulfate radicals generated by the conjunction of peroxymonosulfate with cobalt. Environment Science and Technology 37(20), 4790-4797.

Antonio JG, Maquieira NA, Puchades R. 2010. Determination of atrazine in vegetable samples using a dipstick immunoassay format. IJEAC 82(3), 145-155.

Appleby AP, Franz M, Serge C. 2001. “Weed Control”. Ullmann’s Encyclopedia of Industrial Chemistry. ISBN 3-527-30673-0.

Barchanska H, Jodo E, Price RG, Baranowska I, Abuknesha R. 2012. Monitoring of atrazine in milk using a rapid tube-based ELISA and validation with HPLC. Chemosphere 87(11), 1330-1334.

Baranowska I, Barchanska H, Pacak E. 2006. Determination of triazines herbicides by HPLC and metals by TCP-AES methods. Environment Pollution 143, 206-211.

Barreiro JC, Capelato MD, Martin-Neto L, Bruun Hansen HC. 2007. Oxidative decomposition of atrazine by a Fenton-like reaction in a H2O2/ferrihydrite system. Water Research 41(1), 55-62.

Brooks AJ, Lim HN, Kilduff JE. 2012. Adsorption uptake of synthetic organic chemicals by carbon nanotubes and activated carbons. Nanotechnology 23(29), 294008-294016.

Burken JG, Schnoor JL. 1996. Phytoremediation: plant uptake of atrazine and role of root exudates. Journal of Environment & Engineering 123(11), 958-963.

Castro CS, Guerreiro MC, Gonçalves M, Oliveira LC. Anastácio AS. 2009. Activated carbon/iron oxide composites for the removal of atrazine from aqueous medium. Journal of Hazard Material 164(2-3), 609-614.

Chan KH, Chu W. 2005. Atrazine removal by catalytic oxidation processes with or without UV irradiation Part II: an analysis of the reaction mechanisms using LC/ESI-tandem mass spectrometry. Applied Catalysis B: Environment 58,165-174.

Chen H, Bramanti E, Longo I, Onor M, Ferrari C. 2011. Oxidative decomposition of atrazine in water in the presence of hydrogen peroxide using an innovative microwave photochemical reactor. Journal of Hazard Material 186(2-3), 1808-1815.

Chen S, Lin D, Jiang Z, Zhao J, Gao B, Xiangdong M, Ning J, She D. 2013. Synthesis of C-13-labeled atrazine. Journal of Labell Compounds and Radiopharma 56(5), 305-306.

Chen Z, Wen Q, Lian J, Ren N. 2011. Preparation and characterization of a lipoid adsorption material and its atrazine removal performance. Journal of Environ Science 23(8), 1293-1298.

Cheng J, Liu M, Zhang X, Ding L, Yu Y, Wang X, Jin H, Zhang H. 2007. Determination of triazine herbicides in sheep liver by microwave-assisted extraction and high performance liquid chromatography. Anal Chim Acta 590(1), 34-39.

Collings AF, Gwan PB. 2010. Ultrasonic destruction of pesticide contaminants in slurries. Ultrasonics Sonochem 17, 1–3.

Cooper RL, Stoker TE, Tyrey L, Goldman JM, McElroy WK. 2000. Atrazine disrupts the hypothalamic control of pituitary–ovarian function. Toxicology Science 53, 297-307.

Crain DA, Guillette LJ, Jr, Rooney AA, Pickford DB. 1997. Alterations in steroidogenesis in alligators (Alligator mississippiensis) exposed naturally and experimentally to environmental contaminants. Environment Health Perspective 105, 528-33

Danzo BJ. 1997. Environmental xenobiotics may disrupt normal endocrine function by interfering with the binding of physiological ligands to steroid receptors and binding proteins. Environment Health Perspective 105, 294-301.

Dao YH, De Laat J. 2011. Hydroxyl radical involvement in the decomposition of hydrogen peroxide by ferrous and ferric-nitrilotriacetate complexes at neutral pH. Water Research 45(11), 3309-3317.

Da Silva G, Bozzelli JW, Asatryan R. 2009. Hydroxyl radical initiated oxidation of s-triazine: hydrogen abstraction is faster than hydroxyl addition. Journal of Physical Chemistry A 113(30), 8596-8606.

De Laat J, Truong Le G, Legube B. 2003. A comparative study of the effects of chloride sulfate and nitrate ions on the rates of decomposition of H2O2 and organic compounds by Fe(II)/H2O2 and Fe(III)/H2O2. Chemosphere 55(5), 715-723.

DeLorenzo ME, Scott GI, Ross PE. 2001. Toxicity of pesticides to aquatic microorganisms: a review. Environment Toxicology & Chemistry 20(1), 84-98.

De Souza ML, Sadowsky ML, Wackrtt LP. 1996. Atrazine chlorohydrolase from Pseudomonas sp. strain ADP: gene sequence enzyme purification and protein characterization. Journal of Bacteriology 178, 4894-4900.

De Souza ML, Seffernick ML, Martinez BJ, Sadowsky MJ, Wackett LP. 1998a. The atrazine catabolism genes atzABC are widespread and highly conserved. Journal of Bacteriology 180, 1951-1954.

De Veer I, Moriske HJ, Rüden H. 1994. Photochemical decomposition of organic compounds in water after UV-irradiation: investigation of positive mutagenic effects. Toxicology Letters 72(1-3), 113-119.

Di Corcia A, Marchetti M, Samperi R. 1987. Rapid determination of simazine and atrazine in water at the parts per trillion level. Extraction by a miniaturized carbopack B trap followed by high-performance liquid chromatography. Journal of Chromatography 405, 357-363.

Dong D, Li P, Li X, Zhao Q, Zhang Y, Jia C, Li P. 2010. Investigation on the photocatalytic degradation of pyrene on soil surfaces using nanometer anatase TiO2 under UV irradiation. Journal of Hazard. Material 174, 859–863.

Du Y, Zhao L, Su Y. 2011. Tantalum (oxy)nitrides: preparation characterisation and enhancement of photo-Fenton-like degradation of atrazine under visible light. Journal of Hazard Material 195, 291-297.

Du Y, Zhao L, Chang Y, Su Y. 2012. Tantalum (oxy)nitrides nanotube arrays for the degradation of atrazine in vis-Fenton-like process. Journal of Hazard Material 226, 21-27.

Environmental Protection Agency (EPA) 2003. Interim Reregistration Eligibility Decision for Atrazine pp 2005 (EPA-HQ-OPP-2003-0072-0002) U.S. Environmental Protection Agency Washington DC.

Fang C, Radosevich M, Fuhrmann JJ. 2001. Atrazine and phenanthrene degradation in grass rhizosphere soil. Soil Biology & Biochemistry 3, 671-678.

Gianessi LP, Marcelli MB. 2000. Pesticide use in U.S. crop production 1997: “National Summary Report” National Center for Food and Agricultural Policy.

Grennan K, Strachan G, Porter AJ, Killard AJ, Smyth MR. 2003. Atrazine analysis using an amperometric immunosensor based on single-chain antibody fragments and regeneration-free multi-calibrant measurment. Anal Chim. Acta. 500, 287-298.

Gupta VK, Gupta B, Rastogi A, Agarwal S, Nayak A. 2011. Pesticides removal from waste water by activated carbon prepared from waste rubber tire. Water Research 45(13), 4047-4055.

Hayes TB, Collins A, Lee M, Mendoza M, Noriega N, Stuart AA, Vonk A. 2002. Hermaphroditic demasculinized frogs after exposure to the herbicide atrazine at low ecologically relevant dose. PANS 99, 5476–5480.

Hayes T, Haston K, Tsui M, Hoang A, Haeffele C, Vonk A. 2003. Atrazine-induced hermaphroditism at 0.1 ppb in American leopard frogs (Rana pipiens): laboratory and field evidence. Environmental Health Perspective 111, 568-575.

Hiskia A, Ecke M, Troupis A, Kokorakis A, Hennig H, Papaconstantinou E. 2001. Sonolytic photolytic and photocatalytic decomposition of atrazine in the presence of polyoxometalates. Environment Science & Technology 35(11), 2358-2364.

Ho L, Grasset C, Hoefel D, Dixon MB, Leusch FD, Newcombe G, Saint CP, Brookes JD. 2011. Assessing granular media filtration for the removal of chemical contaminants from wastewater. Water Research 45(11), 3461-3472.

Howard PH. 1989. Handbook of Environmental Fate and Exposure Data for Organic Chemicals. Pesticides. Lewis Publishers Chelsea MI 8-22

Hromadová M, Sokolová R, Pospísil L, Fanelli N. 2006. Surface interactions of s-triazine-type pesticides. An electrochemical impedance study. Journal of Physical Chemistry B 110(10), 4869-4874.

Hutta M, Chalányová M, Halko R, Góra R, Dokupilová S, Rybár I. 2009. Reversed phase liquid chromatography trace analysis of pesticides in soil by on-column sample pumping large volume injection and UV detection. Journal of Sep Science 32(12), 2034-42.

Jones LR, Owen SA, Horrell P, Burns RG. 1998. Bacterial inoculation of granular activated carbon filters for the removal of atrazine from surface water. Water Research 32, 2542 – 2549.

Katz I, Dosoretz CG, Mandelbaum RT, Green M. 2001. Atrazine degradation under denitrifying conditions in continuous culture of Pseudomonas ADP. Water Research 35, 3272 – 3275.

Kidd H, James DR. 1991. The Agrochemicals Handbook Third Edition. Royal Society of Chemistry Information Services Cambridge UK 8-17.

Koal T, Asperger A, Efer J, Engewald W. 2003. Simultaneous determination of a wide spectrum of pesticides in water by means of fast on-line SPE-HPLC-MS-MS – a novel approach. Chromatographia. 57, 93-101.

Krämer W. 2007. Modern Crop Protection Compounds Volume 1. Wiley-VCH.

Kross BC, Vergara A, Raue LE. 1992. Toxicity assessment of atrazine alachlor and carbofuran and their respective environmental metabolites using Microtox. Journal of Toxicological Environment and Health 37, 149-159.

Kuklenyik Z, Panuwet P, Jayatilaka NK, Pirkle JL, Calafat AM. 2012. Two-dimensional high performance liquid chromatography separation and tandem mass spectrometry detection of atrazine and its metabolic and hydrolysis products in urine. Journal of Chromatography B 901, 1-8.

Kumar V, Upadhyay N, Wasit AB, Simranjeet S, Parvinder K. 2013a. Spectroscopic Methods for the Detection of Organophosphate Pesticides –A Preview. Current World Environment 8(2), 313-318.

Kumar V. 2013. Chemical and Biochemical Aspects Decomposition and Environmental Impacts of Monocrotophos-Preview. Journal of Applicable Chemistry 2, 832-840.

Kumar V, Upadhyay N. 2013. Chemical and Biochemical Mechanistic Fate of Acephate. IJSER. 4, 2674-2678.

Kumar V, Upadhyay N, Virender K. 2013b. Mechanistic Approach for the Chemical and Bio-Chemical Aspects of Organophosphate Pesticides. IJCS 11, 945-956.

Kumar V, Upadhyay N, Kumar V, Kaur S, Singh J, Singh S, Datta S. 2014. Environmental Exposure and Health Risks of the Insecticide Monocrotophos-A Review. J. Bio. Env. Sci. 5, 111-120.

Kumar V, Upadhyay N, Singh S, Singh J, Kaur P. 2013c.  Thin-Layer Chromatography: Comparative Estimation of Soil’s Atrazine. Current World Environment 8, 469-473.

Larson DL, McDonald S, Fivizzani AJ, Newton WE, Hamilton SJ. 1998. Effects of the herbicide atrazine on Ambystoma tigrinum metamorphosis: duration larval growth and hormonal response. Physiological Zoology 71, 671-679.

Macyk W, Burgeth G, Kisch H. 2003. Photoelectrochemical properties of platinum(IV) chloride surface modified TiO2. Photochemical & Photobiological Science 2(3), 322-328.

Maleki  N,  Absalan G,  Safavi  A,  Farjami E. 2007. Ultra trace adsorptive stripping voltammetric determination of atrazine in soil and water using mercury film electrode. Anal. Chim. Acta. 581, 37-41.

Mandelbaum RT, Allan DL, Wackett LP. 1995. Isolation and characterization of a Pseudomonas sp. That mineralizes the s-triazine herbicide atrazine. Applied Environmental Microbiology 61, 1451 – 1457.

Matthew K, Ross Toni L, Jones Nikolay M, Filipov. 2009. Disposition of the Herbicide 2-Chloro-4-(ethylamino)-6- (isopropylamino)-s-triazine (Atrazine) and Its Major Metabolites in Mice: A Liquid Chromatography/Mass Spectrometry Analysis of Urine Plasma and Tissue Levels. Drug Metabol. Dispos. 37(4), 776–786.

Nevado JJB, Cabanillas CG, Llerena MJV, Robledo VR. 2007. SPE GCMS-SIM screening of endocrine-disrupting herbicides and related degradation products in natural surface waters and robustness study. Microchemical Journal 87, 62-71.

Oettmeier W. 1999. Herbicide resistance and supersensitivity in photosystem II. Cell Molecular Life Science 55, 1255–1277.

Pearlman WM, Banks CK. 1948. “Substituted chlorodiaminostriazines” Journal of American Chemical Society 70, 3726-3732.

Pommery J, Mathieu M, Mathieu D, Lhermitte M. 1993. Atrazine in plasma and tissue following atrazine-aminotriazole-ethylene glycol-formaldehyde poisoning. Journal of Toxicological Clinical Toxicology 31(2), 323-331.

Pospisil L, Trskova, R, Zalis S, Colombini MP, Fuoco R. 1996. Decomposition Products of s-Triazine

Herbicides by Electron-Transfer in Acidic Aqueous Media. Microchemical Journal 54(4), 367-374.

Prasad R, Upadhyay N, Kumar V. 2013. Simultaneous determination of seven carbamate pesticide residues in gram, wheat, lentil, soybean, fenugreek leaves and apple matrices. Microchem Journal 111, 91-97.

Radosevich M, Traina SJ, Tuovinen OH. 1989. Biodegradation of atrazine in surface soils and subsurface sediments collected from an agricultural research farm. Biodegradation 7, 137 – 149.

Ralston-Hooper KJ, Adamec J, Jannash A, Mollenhauer R, Ochoa-Acuña H, Sepúlveda MS. 2011. Use of GC × GC/TOF-MS and LC/TOF-MS for metabolomic analysis of Hyalella azteca chronically exposed to atrazine and its primary metabolite desethylatrazine. Journal of Applied Toxicology 31(5), 399-410.

Regana F, Meaneya M, Vos JG, MacCraithb BD, Walshb JE. 1996. Determination of pesticides in water using ATR-FTIR spectroscopy on PVC chloroparaffin coatings. Anal. Chimica Acta. 334, 85-92.

Ribeiro AB, Rodríguez-Maroto JM, Mateus EP, Gomes H. 2005. Removal of organic contaminants from soils by an electrokinetic process: the case of atrazine. Chemosphere 59, 1229-1239.

Rhine ED, Fuhrmann JJ, Radosevich M. 2003. Microbial community responses to atrazine exposure and nutrient availability: linking degradation capacity to community structure. Microbial Ecology 46, 145 – 160.

Ross MK, Filipov NM. 2006. Determination of atrazine and its metabolites in mouse urine and plasma by LC-MS analysis. Anal Biochemistry 351(2), 161-173.

Rousseaux S, Hartmann A, Lagacherie B, PiuttiS, Andreux F, Soulas G. 2003. Inoculation of an atrazine-degrading strain Chelatobacter heintzii Cit1 in four different soils: effects of different inoculums densities. Chemosphere 51, 569 – 576.

Rusiecki JA, De Roos A, Lee WJ. 2004. Cancer incidence among pesticide applicators exposed to atrazine in the Agricultural Health Study. Journal of Natl. Cancer Inst. 96, 1375-1382.

Sadowski MJ, Tong Z, Souza MLD, Wackett LP. 1998. AtzC is a new member of the aminohydrolase protein superfamily and is homologous to other atrazine-metabolizing enzymes. Journal of Bacteriology 180, 152 – 158.

Sanderson JT, Letcher RJ, Heneweer M, Giesy JP, van den Berg M. 2001. Effects of chloro-s-triazine herbicides and metabolites on aromatase activity in various human cell lines and on vitellogenin production in male carp hepatocytes. Environtal Health Perspective 109, 1027-1031.

Sanderson JT, Seinen W, Giesy JP, van den Berg M. 2000. 2-Chloro-striazine herbicides induce aromatase (CYP19) activity in H295R human adrenocortical carcinoma cells: a novel mechanism for estrogenicity? Toxicological Science 54, 121-127.

Silva E, Fialho AM, Sa-Correia I, Burns RG, Shaw LJ. 2004. Combined bio-augmentation and bio-stimulation to cleanup soil contaminated with high concentrations of atrazine. Environmental Science & Technology 38, 632 – 637.

Singh P, Suri CR, Cameotra SS. 2004a. Isolation of a member of Acinetobacter species involved in atrazine degradation. Biochemistry Biophysics Research Communications 317, 697 – 702.

Smith D, Alvey S, Crowley DE. 2005. Cooperative catabolic pathways within an atrazine degrading enrichment culture isolated from soil. FEMS Microbiology & Ecology 53, 265 – 273.

Stalikas C, Knopp D, Niessner R. 2002. Sol-Gel Glass Immunosorbent-Based Determination of s-Triazines in Water and Soil Samples Using Gas Chromatography with Nitrogen Phosphorous Detection System. Environmental Science & Technology 36, 3372-3377.

Swan SH, Kruse RL, Liu F. 2003. Semen quality in relation to biomarkers of pesticide exposure. Environtal Health Perspective 111, 1478-84.

Takano A, Takahashi R, Suzuki H, Noguch T. 2008. Herbicide effect on the hydrogen-bonding interaction of the primary quinone electron acceptor QA in photosystem II as studied by Fourier transform infrared spectroscopy. Photosynthetic Research 98, 159–167.

Trebst A. 2007. Inhibitors in the functional dissection of the photosynthetic electron transport system. Photosynthetic Research 92, 217–224.

Turiel E, Fernandez P, Perez-Conde C, Gutierrez AM, Camara C. 1998. Flow-through fluorescence immunosensor for atrazine determination. Talanta 47, 1255-1261.

Usenko S, Hageman KJ, Schmedding DW, Wilson GR, Simonich SL. 2005. Trace analysis of semivolatile organic compounds in large volume samples of snow Lake. Water and Groundwater. Environmental Science & Technology 39, 6006-6015.

Vargha M, Takats Z, Márialigeti K. 2005. Degradation of atrazine in a laboratory scale model system with Danube river sediment. Water Research 39, 1560 – 1568.

Wackett LP, Sadowsky MJ, Martinez B, Shapir N. 2002. Biodegradation of atrazine and related striazine compounds: from enzymes to field studies. Applied Microbiology & Biotechnology 58, 39- 45.

Wert EC, Rosario-Ortiz FL, Snyder SA. 2009. Effect of ozone exposure on the oxidation of trace organic contaminants in wastewater. Water Research 43(4), 1005-1014.

Zadaka D, Nir S, Radian A, Mishael YG. 2011. Atrazine removal from water by polycation-clay composites: effect of dissolved organic matter and comparison to activated carbon. Water Research 43(3), 677-683.

Zhang CZ, Zhang ZY, Liu XJ, Jiang W, Wu Y. 2010. Dissipation and environmental fate of herbicide H-9201 in carrot plantings under field conditions. Food Chemistry 119, 874-879.

Zhang P, Sun H, Yu L, Sun T. 2013. Adsorption and catalytic hydrolysis of carbaryl and atrazine on pig manure-derived biochars: impact of structural properties of biochars. Journal of Hazard Material 245, 217-224.

Zheng W, Guo M, Chow T, Bennett DN, Rajagopalan N. 2010. Sorption properties of greenwaste biochar for two triazine pesticides. Journal of Hazard Material 181(1-3), 121-126.