1,3,5-Triazines hydroxy— from

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). 

Hydroxy butyrate dehydrogenase (from Rhodopseudomonas spheroides) [9028-38-0] Mf 85,000, [EC 1.1.1.30], amorphous. Purified by two sequential chromatography steps on two triazine dye-Sepharose matrices. [Scavan et al. Biochem J 203 699 7952.]... 

Direct bromination readily yields the 6-bromo derivative (111), just as with uracil. Analogous chlorination and iodination requires the presence of alkalies and even then proceeds in low yield. The 6-chloro derivative (113) was also obtained by partial hydrolysis of the postulated 3,5,6-trichloro-l,2,4-triazine (e.g.. Section II,B,6). The 6-bromo derivative (5-bromo-6-azauracil) served as the starting substance for several other derivatives. It was converted to the amino derivative (114) by ammonium acetate which, by means of sodium nitrite in hydrochloric acid, yielded a mixture of 6-chloro and 6-hydroxy derivatives. A modified Schiemann reaction was not suitable for preparing the 6-fluoro derivative. The 6-hydroxy derivative (115) (an isomer of cyanuric acid and the most acidic substance of this group, pKa — 2.95) was more conveniently prepared by alkaline hydrolysis of the 6-amino derivative. Further the bromo derivative was reacted with ethanolamine to prepare the 6-(2-hydroxyethyl) derivative however, this could not be converted to the corresponding 2-chloroethyl derivative. Similarly, the dimethylamino, morpholino, and hydrazino derivatives were prepared from the 6-bromo com-pound. ... 

The 1,2,4-triazine 4-oxides 55 were synthesized by the reaction of nitrones 158 (generated from a-hydroxylamino ketones and aldehydes) with an excess of hydrazine, followed by the oxidation of the intermediate 4-hydroxy-2,3,4,5-tetrahydro-l,2,4-triazines 159 with lead(TV) oxide (73KGS134). 

As previously described, die main intermediates generated from die initial reaction between ortho reactive sites on novolac resins and HMTA are hydroxy-benzylamines and benzoxazines.44 Triazines, diamines, and, in die presence of trace amounts of water, benzyl alcohols and ethers also form (Fig. 7.16). Similar intermediates, with the exception of benzoxazines, are also observed when para sites react with HMTA. 

DAST-type FBAs may contain by-products (such as 11.13) derived from hydrolysis of one or more of the chloro substituents in cyanuric chloride (11.10). One such troublesome byproduct is 2,4-bis(anilino)-6-hydroxy-s-triazine (11.62). Not only is this compound environmentally undesirable, it may also interact with certain bleaching agents and its presence can lead to the development of unpleasant odours on storage of a detergent... 

Pyrrolo[l,2-rf [l,2,4]triazinones 21 were synthesized from methyl ester of /ra j-4-hydroxy-L-proline 72. The synthetic route involved formation of hydrazones followed by cyclisation with orthoesters <1998BMC349>. Similar reactions have been developed with 3-benzylindole-2-carbohydrazides 73 in reaction with triethyl orthoformate, giving the corresponding ring systems indolo[l,2-r][ 1,2,4]triazin-4-oncs 74 <2004JHC7>. 

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). 

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). 

As can be seen, the pathway from the cyclohexadienone to the ortho-rearranged phenol does not imply a jump over an energy barrier (34 kcal/mol), but a tunneling from the vibrational energy levels located at E(vo) = 0 kcal/mol and E(vi) = 3.9 kcal/mol (4.4 kcal/mol for the deuterated compound). Analogous results have been reported for the photo-Fries rearrangement of 2,4-dimethoxy-6-( ara-tolyloxy)-v-triazine (28) to give 2,4-dimethoxy-6-(2-hydroxy-5-meth-ylphenyl)-v-triazine (29) (Scheme 11) [43]. 

The sediment concentrations of anthropogenic compounds in the cove were somewhat less variable than upstream this probably reflects the greater bottom uniformity of the cove. Fewer of the plant s compounds were detected in sediment from the channel where the cove leads into the brackish river (Point 18, Figure 1). Found at this location were various phenols (no. 28, 30a, 30b, 31, 33, 38, 39), di-t-butyl-benzoqui-none (no. 57), 3,5-di-t-butyl-4-hydroxy-benzaldehyde (no. 35), three benzotriazoles (no. 6, 10, 12), 4,4 -dichloro-3(trifluoromethyl) carbanilide (no. 77), and 2-chloro-4,6-bis-isopropylamino-s-triazine (no. 14). The only compounds from the plant detected in the sediment sample from the brackish river (Point 19) were the two high molecular weight benzotriazoles (no. 10 and 12) and methyl 3-(3 ,5 -di-t-butyl-4 -hydroxphenyl) propionate (no. 46). 

Data on the structures of monocyclic dihydro- or hexahydro-1,2,3-triazines, on 1,2,3-triazine tV-oxides and 1,2,3-triazinones are not yet available. From studies on the one-electron reduction of the tetrahydro-l,2,3-triazinium salts (7) it was concluded that the heterocyclic ring is flexible and not planar (80LA285). No detailed information on the structure of 3-benzyl-l,5-diphenyl-l,2-dihydro-l,2,3-triazine-4,6(3//,5f/)-dione (8) or of the 6-hydroxy-4-oxo-l,4-dihydro-l,2,3-triazinium hydroxide inner salts (9) seems to be available. 

As was mentioned already, 3- and 6-phenyl substituted l,2,4-triazin-5-ones exist in the solid state as the 5-hydroxy tautomers, as was shown by IR spectroscopy (74T3171). From UV spectroscopic studies it was suggested that the zwitterionic 2-methyldihydro-l,2,4-triazinium-6-olates (48a) are better formulated as such, rather than as the tautomeric alternatives (48b, 48c) (78JHC1271). 

Hydroxy-l-nitrohydrazones (809) react with primary amines and formaldehyde to give 2,3,4,5-tetrahydro-l,2,4-triazines (810) (64MI21901), and similar compounds (812) can be obtained from the reaction of aldehyde hydrazones (811) with primary amines and aldehydes (74KGS425, 75KGS1290, 74UKZ1220). 

Budziarek and Hampson <71JCS(C)ll67> reported that the reaction between cyanuric chloride and 3-hydroxy-2-naphthanilide occurs in base with an O- triazine to AA-triazine rearrangement (Scheme 42). A stable triazine peroxide (66) has been synthesized from (65) and hydrogen peroxide (77CI(L)232), and (65) forms a novel adduct with the cyclopentadienyl anion (Scheme 43) (68HCA249). 

Nitrogen-containing heterocycles are of obvious interest in the context of prebiotic chemistry. This is the reason why we will now consider this class of derivatives. The first so-called evidence for the presence of 4-hydroxypyrimidine and 4-hydroxy-methyl-pyrimidine in Murchison was published in 197158These results were divergent from those of previous studies performed on Orgueil samples where adenine, guanine, j-triazines and guanylurea were detected 59 60). 

Hydrolytic Dehalogenation Simazine was shown by Roth (1957) to degrade in the presence of com extracts, but was stable in the presence of extracts from a susceptible wheat crop. Castelfranco et al. (1961) described a similar nonenzyme constituent of expressed com sap that hydrolyzed simazine to hydroxysimazine [2,4-bis(ethylamino)-6-hydroxy-y-triazine]. Wahlroos and Virtanen (1959) and Hamilton (1964) have established that the catalytic conversion of simazine to hydroxysimazine in roots and shoots of resistant species is caused by 2,4-dihydroxy-7-methoxy-l,4-benzoxazin-3-one (benzoxazinone) or its 2-glucoside as follows ... 

Frear and Swanson (1970) isolated a soluble glutathione S-transferase from com leaves. Active enzyme preparations were also isolated from leaves of sorghum, sugarcane, johnsongrass, and sudangrass. Appreciable enzyme activity was found only with substituted 2-chloro-.v-triazincs. Substitution of a methoxy, methylmercapto, or hydroxy group in the 2-position of the triazine ring resulted in loss of weed control. 

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