6190-65-4

Usage

Uses

ATRAZINE-DESETHYL has various applications across different industries, primarily due to its unique chemical properties. Here are some of the uses:
Used in Chemical Industry:
ATRAZINE-DESETHYL is used as an intermediate for the synthesis of various chemical compounds, including herbicides and other agrochemicals. Its unique structure allows for the creation of a wide range of products with different applications.
Used in Agricultural Industry:
ATRAZINE-DESETHYL is used as an active ingredient in herbicides for controlling the growth of unwanted plants in agricultural fields. Its effectiveness in controlling a broad spectrum of weeds makes it a valuable tool in modern agriculture.
Used in Environmental Science:
ATRAZINE-DESETHYL is used in environmental studies to understand its behavior in soil and water systems. This knowledge helps in assessing the potential environmental impact of its use in agriculture and developing strategies for minimizing its negative effects.
Used in Pharmaceutical Industry:
ATRAZINE-DESETHYL may also be used as a starting material for the development of new pharmaceutical compounds. Its unique chemical structure can be modified to create new drugs with potential therapeutic applications.

InChI:InChI=1/C6H10ClN5/c1-3(2)9-6-11-4(7)10-5(8)12-6/h3H,1-2H3,(H3,8,9,10,11,12)

Upstream product

• 1912-24-9 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine 

Downstream Products

• 3397-62-4 2-Chloro-4,6-diamino-1,3,5-triazine 

Relevant academic research and scientific papers

Factors affecting formation of deethyl and deisopropyl products from atrazine degradation in UV/H2O2 and UV/PDS

In this study, the formation of deethyl products (DEPs) (i.e., atrazine amide (Atra-imine) and deethylatrazine (DEA)) and deisopropyl product (i.e., deisopropylatrazine (DIA)) from parent atrazine (ATZ) degraded in UV/H2O2 and UV/PDS processes under various conditions was monitored. It was found that SO4- displayed a more distinctive preference to the ethyl function group of ATZ than HO, leading to the higher ratio of DEPs/DIA in UV/PDS system than that in UV/H2O2 system in pure water. The effects of water matrices (i.e., natural organic matter (NOM), carbonate/bicarbonate (HCO3-/CO32-), and chloride ions (Cl-)) on ATZ degradation as well as formation of DEPs and DIA were evaluated in detail. The degradation of ATZ by UV/PDS was significantly inhibited in the presence of NOM, HCO3-/CO32- or Cl-, because these components could competitively react with SO4- and/or HO to generate lower reactive secondary radicals (i.e., organic radicals, carbonate radicals (CO3-) or reactive chlorine radicals (RCs)). The yields of these DEPs and DIA products from ATZ degradation were not impacted by NOM or HCO3-/CO32-, possibly due to the low reactivity of organic radicals and CO3- toward the side groups of ATZ. Howbeit, the increase of DIA yield companied with the decrease of DEPs yield was interestingly observed in the presence of Cl-, which was attributed to the promotion of Cl- at moderate concentration (mM range) for the conversion of SO4- into HO. Comparatively, in the UV/H2O2 process, NOM and HCO3-/CO32- exhibited a similar inhibitory effect on ATZ degradation, while the influence of Cl- was negligible. Differing from UV/PDS system, all these factors did not change DEPs and DIA yields in UV/H2O2 process. Moreover, it was confirmed that RCs had a greater selectivity but a lower reactivity on attacking the ethyl function group than that of SO4-. These findings were also confirmed by monitoring the degradation of ATZ as well as the formation of DEPs and DIA in three natural waters.

The process of atrazine degradation, its mechanism, and the formation of metabolites using UV and UV/MW photolysis

The photolytic degradationmechanism of atrazine using a UV reactor andUV/MW (electrodeless discharge lamp (Hg-EDL)) was investigated. After 120?s of UV photolysis partial degradation of atrazine had been observed and a subsequent formation of degradation products of atrazine-2-hydroxy, therefore, defining the path of atrazine degradation through UV photolysis. This system after 1200?s of exposure to UV radiation had not reached full degradation of atrazine, and its metabolite (atrazine-2-hydroxy), was the main by-product obtained for the process. When performing photolysis through the UV/Microwave combined methodcomplete atrazine degradation was obtained within a 5?s interval, besides the formation of five (5) degradation products, which are HAT, DEAT, DIAT, DEHAT and DIHAT. Therefore, defining the path of the photolytic degradation process through the UV/Microwave combined method. The total degradation of its metabolite (HAT) was observed for the period of 120?s of exposure to UV/MW radiation, and after that time there had been no signcorresponding to the respective compounds. The tests with the isolated microwave radiation were not efficient in the degradation of the atrazine and, therefore, the respective isolated energy is not applicable.The control of atrazine degradation and consequent formation of metabolites were accompanied by a high-performance liquid chromatography with a UV/Vis detector.

Efficient removal of atrazine in water with a Fe3O4/MWCNTs nanocomposite as a heterogeneous Fenton-like catalyst

Fe3O4 and multi-walled carbon nanotube hybrid materials (Fe3O4/MWCNTs) were synthesized by a coprecipitation combined hydrothermal method. The nanocomposites were applied for adsorption and degradation of atrazine (ATZ) in the presence of H2O2. The obtained catalysts were characterized by TEM, XRD, BET, XPS and Raman spectroscopy. The effects of solution pH, catalysts dosage, H2O2 concentration and iron leaching on the degradation of ATZ were investigated. Fe3O4/MWCNTs showed a higher utilization efficiency of H2O2, higher ability of adsorption for ATZ and higher degradation efficiency of ATZ than Fe3O4 nanoparticles in the batch degradation experiment. The degradation efficiency increased with the solution pH decreasing from 8.0 to 3.0. The catalytic results showed that Fe3O4/MWCNTs presented good performance for the degradation of ATZ, achieving 81.4% decomposition of ATZ after 120 min at reaction conditions of H2O2 concentration 3.0 mmol L-1, catalysts dosage 0.1 g L-1, ATZ concentration 10.0 mg L-1, pH 5.0 and T 30 °C. Three degradation products (desethylatrazine, desisopropylatrazine, and 2-hydroxyatrazine) were detected during a heterogeneous Fenton reaction in solution. The stability, and reusability of Fe3O4/MWCNTs for ATZ degradation were also investigated.

Cytochrome P450-catalyzed dealkylation of atrazine by Rhodococcus sp. strain NI86/21 involves hydrogen atom transfer rather than single electron transfer

Cytochrome P450 enzymes are responsible for a multitude of natural transformation reactions. For oxidative N-dealkylation, single electron (SET) and hydrogen atom abstraction (HAT) have been debated as underlying mechanisms. Combined evidence from (i) product distribution and (ii) isotope effects indicate that HAT, rather than SET, initiates N-dealkylation of atrazine to desethyl- and desisopropylatrazine by the microorganism Rhodococcus sp. strain NI86/21. (i) Product analysis revealed a non-selective oxidation at both the αC and βC-atom of the alkyl chain, which is expected for a radical reaction, but not SET. (ii) Normal 13C and 15N as well as pronounced 2H isotope effects (εcarbon: -4.0‰ ± 0.2‰; εnitrogen: -1.4‰ ± 0.3‰, KIEH: 3.6 ± 0.8) agree qualitatively with calculated values for HAT, whereas inverse 13C and 15N isotope effects are predicted for SET. Analogous results are observed with the Fe(iv)O model system [5,10,15,20-tetrakis(pentafluorophenyl)porphyrin-iron(iii)- chloride + NaIO4], but not with permanganate. These results emphasize the relevance of the HAT mechanism for N-dealkylation by P450.

Metalloporphyrins as biomimetic models for cytochrome P-450 in the oxidation of atrazine

The aim of this work was to evaluate whether metalloporphyrin models could mimic the action of cytochrome P-450 in the oxidation of atrazine, a herbicide. The commercially available second-generation metalloporphyrins 5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrin metal(III) chloride [M(T-DCPP)Cl] and 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin metal(III) chloride [M(TFPP)Cl] (metal = Fe or Mn) and the oxidants iodosylbenzene and metachloroperbenzoic acid were employed in this study. Results showed that the metalloporphyrins used here can oxidize atrazine. Yields as high as 32% were obtained for the Mn(TFPP)Cl/PhIO system, which shows that these catalysts can mimic both the in vivo and the in vitro action of cytochrome P-450, with formation of the metabolites DEA and DIA. The formation of five other unknown products was also detected, but only one of them could be identified, since the other four were present in very low concentrations. The compound COA, identified by mass spectrometry, was the main product in most of the oxidation reactions.

Wet peroxide degradation of atrazine

The high temperature (150-200 °C), high pressure (3.0-6.0 MPa) degradation of atrazine in aqueous solution has been studied. Under these extreme conditions atrazine steadily hydrolyses in the absence of oxidising agents. Additionally, oxygen partial pressure has been shown not to affect atrazine degradation rates. In no case mineralisation of the parent compound was observed. The addition of the free radical generator hydrogen peroxide to the reaction media significantly enhanced the depletion rate of atrazine. Moreover, partial mineralisation of the organics was observed when hydrogen peroxide was used. Again, oxygen presence did not influence the efficiency of the promoted reaction. Consecutive injections of hydrogen peroxide throughout the reaction period brought the total carbon content conversion to a maximum of 65-70% after 40 min of treatment (suggesting the total conversion of atrazine to cyanuric acid). Toxicity of the effluent measured in a luminometer decreased from 93% up to 23% of inhibition percentage. The process has been simulated by means of a semi-empirical model.

Manganese dioxide as a catalyst for oxygen-independent atrazine dealkylation

The herbicide atrazine is widely distributed in the environment, and its reactivity with soil minerals is an important issue. We have studied atrazine degradation on the surface of synthetic hydrous (10% H2O) δ-MnO2 (birnessite) using UV resonance Raman spectroscopy and gas chromatography. The products are mainly mono-and didealkyl atrazine. Atrazine disappearance is rapid (τ(1/2) ~ 5 h at 30 °C), independent of whether O2 is present or not. MnO2 reduction is a minor reaction, and the alkyl chains are converted mainly to the alkenes, in a nonredox process. A novel dealkylation mechanism is proposed involving proton transfer to Mn(IV)-stabilized oxo and imido bonds. When O2 is present, olefin oxidation and ring mineralization are also observed as secondary reactions in addition to those discussed above. Thus δ-MnO2, a common soil constituent, is found to promote efficient N- dealkylation of the herbicide atrazine at 30 °C, via a nonoxidative mechanism. The herbicide atrazine is widely distributed in the environment, and its reactivity with soil minerals is an important issue. We have studied atrazine degradation on the surface of synthetic hydrous (10% H2O) δ-MnO2 (birnessite) using UV resonance Raman spectroscopy and gas chromatography. The products are mainly mono- and didealkyl atrazine. Atrazine disappearance is rapid (τ1/2 approximately 5 h at 30 °C), independent of whether O2 is present or not. MnO2 reduction is a minor reaction, and the alkyl chains are converted mainly to the alkenes, in a nonredox process. A novel dealkylation mechanism is proposed involving proton transfer to Mn(IV)-stabilized oxo and imido bonds. When O2 is present, olefin oxidation and ring mineralization are also observed as secondary reactions in addition to those discussed above. Thus δ-MnO2, a common soil constituent, is found to promote efficient N-dealkylation of the herbicide atrazine at 30 °C, via a nonoxidative mechanism.

Study of the mechanisms of the photodegradation of atrazine in the presence of two photocatalysts: TiO2 and Na4W10O32

The mechanisms of the photodegradation of atrazine under direct photolysis and in the presence of two different photocatalysts, TiO2 and Na4W10O32, are investigated by the means of GC/MS, total radioactivity counting, HPLC and TLC analysis on 14C ring-labelled atrazine solutions. Integration of photo- and biodegradation processes is studied.

Identification of Fenton's reagent-generated atrazine degradation products by high-performance liquid chromatography and megaflow electrospray ionization tandem mass spectrometry

High-performance liquid chromatography megaflow electrospray tandem mass spectrometry (HPLC/ES-MS/MS) with an on-line radioisotope detector was used to identify [2,4,6-14C]atrazine degradation products generated by treatment with Fenton's reagent (Fe2+ and H2O2). Fenton's reagent produced dealkylated and/or partially oxidized [2,4,6-14C]atrazine products in preference to dechlorinated products. Seven major products were identified by collision-induced dissociation spectra: 4-acetamido-2-chloro-6-(isopropylamino)-s-triazine, 4-amino-2-chloro-6-(isopropylamino)-s-triazine, 4-acetamido-2-chloro-6-(ethylamino)-s-triazine, 6-amino-2-chloro-4(ethylamino)-s-triazine, 4-acetamido-6-amino-2-chloro-s-triazine, 2-chloro-4,6-diamino-s-triazine and the first report of 4-acetamido-2-hydroxy-6-(isopropylamino)-s-triazine. HPLC/ES-MS/MS provided a rapid method for identifying a wide range of atrazine transformation products in aqueous samples and obviated the need for fraction collection, extraction, and chemical derivatization of the more polar atrazine products. Furthermore, because analyte retention times in HPLC/UV and HPLC/ES-MS/MS were similar, compound identities determined using the latter could be directly assigned to peaks in UV chromatograms.