4,6-Diamino-s-triazin

The catalytic effect of protons, of bifunctional catalysts, and of base is demonstrated in the amination of chloro derivatives of pyridazine, pyrimidine, and s-triazine (Tables V and VI). Anilino-s-triazines containing NH groups act as catalysts in their own formation. The catalytic action of protons on anhino-dechlorination of 2-chloro-4,6-diamino-s-triazine and of 2-amino-4-chloropyrimidine was reported in the classic paper by Banks. ... 

Chlorocatechol, see 4-Chlorophenol. 2,4-D, 2,4,5-T 4-Chloro-o-cresol, see MCPA 2-Chloro-4,6-diamino-s-triazine, see Atrazine. 

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). 

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). 

In the presence of hydroxy or perhydroxy radicals generated from Fenton s reagent, simazine undergoes dealkylation to give 2-chloro-4,6-diamino-s-triazine as the major product (Kaufman and Kearney, 1970). 

The conversion of biguanides into guanamines under the influence of acylating agents is well known (see also Section VII 12). Acetic anhydride or benzoyl chloride in conjunction with alkali react with the parent compound, gelding 2-methyl- 519) or 2-phenyl-4,6-diamino-s-triazine 17) (LXXXI R = Me or Ph) respectively. 

Diamino-s-triazine-2-oL See Ammeline in Yoi 1, p A273-R and its Dinitramino deriv, Dinitroammeline, p A274-L... 

Ammeline 4,6-Diamino-s-triazin-2-ol or 3, 4,5,6-Tetrabydro-4,6-diimino s-triazin-2( 1 Hi-one, called in Beil 6-Oxo-2.4-diimino-hexahydro-1.3.5-triazin Isocyaniirs ure-diimid or 2-Oxy 4.6-diamino-1.3.5-triazin,... 

Diamino-s-triazine-2-ol see Ammeline 1 A273 (4,6-Diamino-s-triazine-2-yl)-guanidine... 

Chloromethyl-4,6-diamino-s-triazine can be prepared in 82% yield by stirring a mixture of biguanide and ethyl chloroacetate in methanol in the same way. 

DP = dipolar aprotic solvent NMP = iV-methyl pyrrolidinone OAAT = 2-hydroxy-4,6-diamino-.s -triazine OIET = 2-hydroxy-4-(isopropylamino)-6-(ethylamino)-5-triazine OOAT = 2-hydroxy-4-hydroxy-6-amino-s-triazine PS = petroleum sulfide TBA = tetra-n-butylammonium TEA = tetraethylammonium TEOS = tetramethylorthosilicate TMA = tetramethylammonium TMU= tetramethylurea. c For reactions photoca-talyzed by POMs under anaerobic conditions, the reduced POM resulting from photooxidation of the substrate is reoxidized by reduction of protons generated in this initial substrate photooxidation step, forming H2. 

S Q a. o Menazon Saphos S- (4,6-diamino-s-triazin-2-ylmethyl) -0,0-dimethylphos-phorodithioate... 

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