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Atrazine: Comparison
Please note this is a comparison between Version 3 by Catherine Yang and Version 2 by JUNTING HONG.

Atrazine, an herbicide used to control grassy and broadleaf weed, has become an essential part of agricultural crop protection tools. It is widely sprayed on corn, sorghum and sugar cane, with the attendant problems of its residues in agri-food and washing water. If ingested into humans, this residual atrazine can cause reproductive harm, developmental toxicity and carcinogenicity. It is therefore important to find clean and economical degradation processes for atrazine.

  • atrazine
  • degradation
  • residue
  • agri-food
  • water

1. Introduction

Atrazine (Figure 1) is a triazine herbicide with a wide range of applications, for grassy and broadleaf weed control in corn, sugarcane, sorghum and certain other crops [1,2,3,4][1][2][3][4]. Due to of its efficiency and low cost, its average consumption worldwide is 70,000 to 90,000 tons per year [5]. If shopping for conventional groceries, consumers are likely to have eaten food that has been sprayed with atrazine. Since atrazine is applied to crops used as livestock feed, its residues are found not only in crops, but also in milk and meat. According to the consumer risk assessment performed by the European Food Safety Authority [6], atrazine input values used for the dietary chronic exposure calculation of maize and other cereals except maize are 0.025 mg/kg and 0.05 mg/kg, respectively, based on the mean consumption data representative for 22 national diets. Although not considered acutely toxic to people, atrazine affects long term human health. Atrazine can act as the endocrine disrupting chemicals (EDC) [7], that can produce damage to the endocrine system, and cause a series of pathological changes and reproductive abnormalities [8]. Additionally, atrazine is also a potential carcinogen due to negative impact on human health such as tumors, breast, ovarian, and uterine cancers as well as leukemia and lymphoma [9]. For these reasons, atrazine was banned in the European Union (EU) in 2003.However, the commercial formulations of the herbicide atrazine (such as Gesaprim 90% WG) are still widely employed in Latin America. For example, herbicides were the main pesticide class used in Brazil between 2009 and 2018, with oscillations from 52.4% (2011) to 62.5% (2012), and atrazine was the top two active ingredient in this period. [11][10]. Brazil is the world’s third biggest exporter of agricultural products and organic food market leader in Latin America [12][11]. In addition, Brazil’s main export markets are the European Union and the United States [13][12]. So, the residual problem of atrazine still remains a concern. Atrazine is chemically stable with long half-life in water (30–100 days) [14[13][14],15], and its microbial degradation in soil environments is a relatively slow process (the range of field half-lives is 18 to 148 days [16,17][15][16]). It is also slightly soluble in water (33 mg.L−1 at 22 °C) and has low adsorption in soil [18][17]. Thus, it contaminates both surface and ground water [19][18]. The upper limit for atrazine in drinking water is 3 μg/L in America whereas in Europe, it is fixed as 1 μg/L [20,21][19][20]. However, investigations [22,23,24][21][22][23] have shown that concentrations of atrazine exceed the authorized limit of water contamination in surface water and ground water. Lots of works [25,26,27,28][24][25][26][27]have been conducted on the detection and quantification of atrazine in water, which is important to the food safety and quality control. Controlling the pollution of residual atrazine in agri-food and washing water has become a major issue.

Figure 1.

Atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine).

2. Biodegradation

Biodegradation refers to the partial, and sometimes total, transformation or detoxification of contaminants by microbial, plants or enzymes [118][28]. It has advantages over physical and chemical methods in terms of low costs and environmental friendliness [119][29]. Since the discovery of biotic atrazine degradation [120[30][31],121], biodegradation has been a major method for atrazine catabolism [1].

2.1. Microbial Degradation

Microbial degradation exploits the ability of microorganisms for removal of pollutants from contaminated sites [122][32]. That is because indigenous microorganisms that are already present in polluted environments may transform pollutants to harmless products via reactions that take place as a part of their metabolic processes [123][33]. Generally, isolated microbes are selected for the degradation due to nature and type of pollutants. Different atrazine-degrading bacteria and fungi have been isolated (Table 5Table 1). Because microorganisms are easily drained in water making their effectiveness greatly reduced, Yu et al. [58][34] developed a self-immobilized biomixture (SIB) with biosorption and biodegradation properties, that can obtain better atrazine removal rate.

Table 51.

Microbial degradation of aqueous atrazine.

Strain Origin Removal Effect
Arthrobacter sp. DNS10 Black soil [54][35] The removal rate of 100 mg/L atrazine reached 95% and 86% in 0.05 mM Zn2+ and 1.0 mM Zn2+, respectively at 48 h [55][36].
Bacillus badius ABP6 Maize fields Response-surface-methodology (RSM) was used to optimize environmental factors such as pH, temperature, agitation speed and atrazine-concentration on atrazine degradation by utilizing Bacillus badius ABP6 strain. In the optimum conditions (pH 7.05, temperature 30.4 °C, agitation speed 145.7 rpm, and atrazine-concentration 200.9 ppm), the degradation rate of atrazine reaches a maximum value of 90% [56][37].
Bjerkanderaadusta Rotten wood surfaces In the optimum conditions (pH 4, temperature 28 °C, biomass 2 g, and atrazine-concentration 50 ppm), the removal rate of atrazine was up to 92% in 5 days [57][38].
Agrobacterium sp. WL-1, 
44],61], and the molecular mechanism for catabolism and detoxification of atrazine in plants is a major research topic (Table 62).
Table 62.
 Phytodegradation of aqueous atrazine.
Plant Gene/Enzymes Result
Pennisetum cladestinum Soil dehydrogenase Within 80 days, nearly 45% of atrazine was degraded [59][42].
Rice Two novel methyltransferases LOC_Os04g09604, LOC_Os11g15040 Atrazine degradation and detoxification are regulated [62][45]
Alfalfa (Medicago sativa) Genes encoding glycosyltransferases, glutathione S-transferases or ABC transporters Atrazine in alfalfa can be detoxified through different pathways [63][46].
Arthrobacter sp. ZXY-2 Jilin Pesticide Plant After adding biochar ZXY-2 pellets, the removal rate of atrazine reached 61% within 1 h, higher than that treated by ZXY-2 pellets without biochar. The addition of biochar could enhance the connection between ZXY-2 and pellets-based carrier, and the favorable biodegradation pH of ZXY-2 changed to 6 and 10 [58][34].
Chlorella sp. The Freshwater Algae Culture Collection at the Institute of Hydrobiology, China Atrazine with initial concentration of 5 mg/L was photocatalytic degraded for 60 min with degradation ratio of 31%. After an 8 d exposure of the microalga Chlorella sp., 83% and 64% of the atrazine were removed from the degraded solutions containing 40 μg/L and 80 μg/L of atrazine, respectively [124][39].
Myriophyllum spicatum Wuhan Botanical Garden Myriophyllum spicatum absorbed more than 18-fold the amount of atrazine in sediments and degraded atrazine to hydroxyatrazine (HA), deelthylatrazine (DEA), didealkylatrazine (DDA), cyanuric acid (CYA) and biuret. The formation of biuret suggested for the first time, the ring opening of atrazine in an aquatic plant. The residual rate of atrazine was 6.5 ± 2.0% in M. spicatum-grown sediment on day 60 [125][40].

2.2. Phytodegradation

The phytodegradation of organic compounds take place inside the plant or within the rhizosphere of the plant [126][41]. Rhizosphere, the immediate vicinity of plant roots, is a zone of intense microbial activity, and the use of vegetation at the waste sites can overcome the inherent limitations such as low microbial population or inadequate microbial activity [59][42]. It has been reported that atrazine can be degraded or detoxified in crops [60[43][
Generally, atrazine may be degraded within the plant biomass by plant enzymes as well as in its rhizosphere by microbial biotransformation [127,128][47][48].

3. Degradation Pathways, Atrazine Mineralization and Metabolites Toxicity

The degradation of atrazine is a complex process with different pathways through different biotic or abiotic water treatment processes. Regarding the biotic degradation processes, there are two stages [146][49] (Figure 32). In the first stage, hydrolytic dichlorination and N-dealkylation of atrazine generate cyanuric acid in the role of the enzymes that have broad substrate specificity [147][50]. For hydrolytic dichlorination of atrazine, enzyme atrazine chlorohydrolase (AtzA) [148][51] or hydrolase triazine (TrzN) [149][52] catalyzes hydrolytic dichlorination of atrazine, but they display substantial differences in their substrate ranges: AtzA is restricted to atrazine analogs with a chlorine substituent at carbon 2 and N-alkyl groups, ranging in size from methyl to t-butyl [150][53], and TrzN hydrolyzes a range of leaving groups (e.g., OCH3, –SCH3, –Cl, –F, –CN) from both triazines and pyrimidines [149][52]. For N-dealkylation of atrazine, hydroxyatrazine N-ethylaminohydrolase (AtzB) [151][54] catalyzes the hydrolytic conversion of hydroxyatrazine to N-isopropylammelide, and N-isopropylammelide isopropylaminohydrolas (AtzC) [152][55] catalyzes the hydrolysis of N-isopropylammelide to cyanuric acid. In the second stage, cyanuric acid is converted to ammonium and carbon dioxide by a set of enzymes AtzDEF [153,154][56][57] and TrzD [153,155][56][58].
Figure 32.
 Degradation pathway of atrazine through biotic treatment process.
The above discussion is based on the enzymatic steps catalyzed by the gene products. In actual operation, atrazine degradation may be achieved by a consortium of organisms harboring the appropriate combination of enzymes, for example, the enriched mixed culture as well as the isolated strain, designated as Arthrobacter sp. strain GZK-1, mineralized 14C-ring-labeled atrazine up to 88% to 14CO2 in a liquid culture within 14 d [156][59]. In addition, for abiotic water treatment processes, as shown in Section 2 and Section 3 of this article, many advanced oxidation processes (AOPs) have been involved in the degradation of atrazine in water. These AOPs can be used individually or in combination to improve efficiency such as US/UV [71[60][61],157], US/UV/O3 [114[62][63],158], electrochemistry (EC)/O3 [111][64], UV/H2O2 [159][65], UV/US/PS [160][66], UV/MW [161[67][68],162], UV/Fenton [83][69], etc. Generally, AOPs rely on the in situ formation of reactive species [78][70], such as hydroxyl radical (•OH) [163][71], sulfate radical (SO4•−) [164[72][73],165], singlet oxygen (1O2) [132][74], superoxide radical anions (O2•−) [37][75], hydrated electron (eaq−) [78][70] and hydrogen radical (H•) [78][70]. These reactive species have different redox potential and reaction selectivity. Therefore, the degradation pathways of atrazine vary from different AOPs. The general involved mechanisms were de-chlorination, hydroxylation of the s-triazine ring, de-alkylation of the amino groups, oxidation of the amino groups, de-amination and the opening of the s-triazine ring [71][60] (Figure 43). In most previous works [71[60][62][73][74][76],92,114,132,165], the final products of atrazine degradation tend to be cyanuric acid, ammelide and ammeline, because it is difficult to cleave the s-triazine ring [166][77]. At present, few studies [45,75,81,167,168][78][79][80][81][82] have reported the complete mineralization of atrazine, in which s-triazine ring-cleavage produced the less toxic compound biuret [167][81], and biuret hydrolyzed to allophanate, followed by the final generation of CO2, H2O, NH4+ and small acids. The complete mineralization of atrazine thus reduces the toxicity of the treated wastewater for subsequent release.

Figure 43. General involved degradation mechanisms of atrazine: (a) dealkylation of the amino groups; (b) dechlorination and hydroxylation of the s-triazine ring; (c) oxidation of the amino groups and deamination; (d) the opening of the s-triazine ring.

Toxicity studies on atrazine degradation are still incomplete, because some atrazine metabolites such as ammeline lack toxicological data. According to the book “Pesticide residues in food: 2007, toxicological evaluations”, published by the World Health Organization [169][83], atrazine, and its chloro-s-triazine metabolites are of moderate or low acute oral toxicity in male rats (LD50), 1870–3090, 1890, 2290 and 3690 mg/kg bw for ATZ, DEA, DIA and DDA, respectively; and the acute oral toxicity of hydroxyatrazine in male rats (LD50, >5050 mg/kg bw) is lower than that of atrazine or its chlorometabolites. However, toxicity comparisons based on these LD50 values are still inaccurate, as the results of toxicity tests vary based on different subjects (plants, animals, human cells, etc.) or different concerns (reproductive or developmental toxicity, liver toxicity, etc.). More toxicity tests data are shown above (Table 8Table 3). Combining these data, the following toxicity ranking can be roughly obtained: atrazine (ATZ) > deethylatrazine (DEA) > deisopropylatrazine (DIA) > ammeline (AM) > didealkylatrazine (DDA) > hydroxyatrazine (HA).

Table 83.

Chemical structures and toxicity tests data of atrazine and its metabolites.

Name Atrazine (ATZ) Deeth-Ylatrazine (DEA) Deisoprop-Ylatrazine (DIA) Ammeline (AM) Cyanuric Acid Dideal-Kylatrazine (DDA)

Hydroxy-Atrazine (HA)
Chemical structure 食品 11 02416 i001 食品 11 02416 i002 食品 11 02416 i003 食品 11 02416 i004 食品 11 02416 i005 食品 11 02416 i006 食品 11 02416 i007
Acute oral toxicity in male rats (LD50) [169][83] 1870–3090 mg/kg 1890 mg/kg 2290 mg/kg     3690 mg/kg >5050 mg/kg
Median lethal concentrations (LC50) for Pseudokirchneriella subcapitata in 96 h of exposure [170][84] 1600 μg/L 2000 μg/L >3000 μg/L        
Concentration for 50% of maximal effect (EC50) on algal photosynthesis for A. variabilis [171][85] 0.1 ppm 0.7 ppm 4.7 ppm     100 ppm >100 ppm
Acute oral toxicity in rats (LD50) [171][85]         >5000 mg/kg    
Adverse effects in sheep [172][86]       An average daily intake of ammeline 296 mg/kg body weight per day for 42 days for sheep caused half death. No adverse effects at doses from 198 to 600 mg/kg body weight per day for 77 days.    
In addition, Banghai Liu et.al. [90][87] used the ECOSAR program to predict the acute and chronic toxicity of atrazine and its transformation intermediates, and it was found that although the vast majority of detected products possessed lower toxicity compared to atrazine, they remained classified as very toxic compounds to aquatic organisms.

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