2-Amino-4-chloro-6-isopropylamino-1,3,5-triazine

Janthinellum yielded 2-chloro-4-amino-6-isopropylamino-5-triazine and Rhizopus stolonifer yielded 2-chloro-4-(ethylamino)-6-amino-5-triazine (Paris and Lewis, 1973). Atrazine was transformed by the culture Nocardia forming 2-chloro-4-amino-5-triazine (Giardina et al, 1980,1982). 

Plant. In tolerant plants, atrazine is readily transformed to hydroxyatrazine which may degrade via dealkylation of the side chains and subsequent hydrolysis of the amino groups with some evolution of carbon dioxide (Castelfranco et al, 1961 Roth and Knuesli, 1961 Humburg et al, 1989). In corn juice, atrazine was converted to hydroxyatrazine (Montgomery and Freed, 1964). In both roots and shoots of young bean plants, atrazine underwent monodealkylation forming 2-chloro-4-amino-6-isopropylamino-s-triazine. This metabolite is less phytotoxic than atrazine (Shimabukuro, 1967). 

Chemical/Physical. The hydrolysis half-lives of atrazine in O.lM-HCl, buffer at pH 5.0, and O.lM-NaOH solutions at 20 °C were 9.5, 86, and 5.0 d, respectively. Atrazine degraded to 2-chloro-4-amino-6-isopropylamino-5-triazine (Burkhard and Guth, 1981). 

In the presence of hydroxy or perhydroxy radicals generated from Fenton s reagent, atrazine undergoes oxidative dealkylation in aqueous solutions (Kaufman and Kearney, 1970). Major products identified by GC/MS included deisopropylatrazine (2-chloro-4-ethylamino-6-amino-s-triazine), 2-chloro-4-amino-6-isopropylamino-5-triazine, and a dealkylated dealkylatrazine (2-chloro-4,6-diamino-s-triazine) (Kaufman and Kearney, 1970). 

The primary ozonation by-products of atrazine (15 mg/L) in natural surface water and synthetic water were deethylatrazine, deisopropylatrazine, 2-chloro-4,6-diamino-s-triazine, a deisopropylatrazine amide (4-acetamido-4-amino-6-chloro-5-triazine), 2-amino-4-hydroxy-6-isopropylamino-5-triazine, and an unknown compound. The types of compounds formed were pH dependent. At high pH, low alkalinity, or in the presence of hydrogen peroxide, hydroxyl radicals formed from ozone yielded 5-triazine hydroxy analogs via hydrolysis of the Cl-Cl bond. At low pH and low alkalinity, which minimized the production of hydroxy radicals, dealkylated atrazine and an amide were the primary byproducts formed (Adams and Randtke, 1992). 

Shimabukuro et al. (1966) identified 2-chloro-4-amino-6-isopropylamino-i-triazine (G-30033) as a major metabolite in shoots of mature pea plants. These results indicated that a second mechanism for tolerance to atrazine existed in some moderately susceptible plants. Later, Shimabukuro (1967a) was able to demonstrate that atrazine could be metabolized independently in both roots and shoots of young pea plants to 2-chloro-4-amino-6-isopropylamino-.t-triazine. This metabolite was much less phytotoxic than the parent compound. The metabolism of atrazine in resistant com and sorghum, in intermediately susceptible pea, and in highly susceptible wheat was reported by Shimabukuro (1967b). This study revealed two possible pathways for metabolism of atrazine in higher plants. All species studied were able to metabolize atrazine by TV-deal kyI ation of either of the two alkyl groups present. Com and wheat that contain the cyclic hydroxyamate (2,4-dihydroxy-7-methoxy-l,4-benzoxazine-3-one) also metabolized atrazine by conversion to hydroxy-atrazine (G-34048). Subsequent metabolism was postulated to be by conversion to more polar compounds. 

Synonyms 2-chloro-4-ethylamino-6-isopro-pylamino-1,3,5-triazine 1- chloro-3-ethyl-amino-5-isopropylamino-i-triazine Atra-tol Atrex Penatrol... 

Figure 11. Intermediates identified in the microbial degradation of atrazine a, in Aspergillus fumigatus Fres. [176] b, in Nocardia sp. [180] c, in Pseudomonas sp. [182]. I, 2-chloro-4-amino-6-isopropylamino-S-triazine II, 2-chloro-4-ethylamino-6-amino-S-triazine III, 4-amino-2-chloro-S-triasine IV, 2-hydro3y-4-amino-6-isopropylamino-S-triazine V, 2-hydroxy-4-ethylamino-6-amino-S-triazine VI, 2-hydroxy-4,6-diamino-S-triazine.

Atrazine and four metabolites generated from topical applications [2-hydroxy-4-ethylamino-6-isopropylamino-s-triazine, 2-chloro-4-ethylamino-6-amino-s-triazine, 2-chloro-4-amino-6-isopropylamino-s-triazine, 2-hydroxy-4,6-diamino-s-triazine) were resolved on a C g column (A = 223 nm). A 14-min 20/80 -> 50/50 acetonitrile/water gradient was used [996]. The assay was linear from 2 to 120pg/mL (20 pL injections). Peak shapes and resolution were good. 

Cotterill [100] studied the effect of ammonium nitrate fertilizer on the electron capture or nitrogen specific gas chromatographic determination of Triazine plus other types of herbicide (Atrazine(2-chloro-4-ethylamino-6-isopropylamino, 1,3,5 triazine), Simazine (2-chloro-4.6 bis ethyl amino 1,3,5 triazine), Linuron (3,4,-chlorophenyl-l-methoxy-l-methyl urea), Metribuzin, Triallate and Phorate) residues in soil. 

The dye-sensitized photodecomposition of atrazine was studied in aqueous, aerated solutions. When the solution was irradiated in sunlight for several hours, 2-chloro-4-(isopropyl-amino)-6-amino-s-triazine and 2-chloro-4-(isopropylamino)-6-acetamido-s-triazine formed in yields of 70 and 7%, respectively (Rejto et al, 1983). Continued irradiation of the solution led to the formation of 2-chloro-4,6-diamino-s-triazine which eventually degraded to unidentified products. Hydroxyatrazine was the major intermediate compound formed when atrazine (100 mg/L) in both oxygenated estuarine water (Jones, 1982 Mansour et ah, 1989) and estuarine sediments were exposed to sunlight. The rate of degradation was slightly greater in water (half-life 3-12 d) than in sediments (half-life 1-4 wk) (Jones et al., 1982). 

Purkayastha and Cochrane [155] compared electron capture and electrolytic conductivity detectors in the gas chromatographic determination of Prometon, Atraton (2-ethylamino-4-isopropylamino-6-methoxy-l,3,5-triazine), Propazine, Atrazine (2-chloro-4-ethylamino-6-isopropyl-amino-l,3,5-triazine), Prometryne, Simazine (2-chloro-4,6-6/s-ethylamino-l,3,5-triazine) and Ametryne (2-ethylamino-4-isopropylamino-6-methyl-thio-1,3,5-triazine) in inland water samples. They found that the electrolytic conductivity... 

Among the 2-chloro-4,6-bis(alkylamino)-i-triazines with two different substituent side-chains, 2-chloro-4-ethylamino-6-isopropylamino-i-triazine (atrazine, 8) is the most active, and followed, in decreasing order of activity, by 2-chloro-4-ethylamino-6-5ec-butylamino-i-triazine (sebuthylazine, 9) and 2-chloro-4-ethyl-amino-6-/-butylamino-j-triazine (terbuthylazine, 10). 

Among the 2-chloro-4-alkylamino-6-dialkylamino-5-triazines, 2-chloro-4-ethyl-amino-6-diethylamino-5-triazine (trietazine, II) and 2-chloro-4-isopropylamino-... 

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