1,3,5-Triazine, phenoxy-, amination

Chloro-4,6-diphenyl- and 2-chloro-4,6-dimethyl- -triazines (318) undergo facile nucleophilic displacements with ammonia, amines, and hydrazine, with alkoxide, or with hydrosulfide ions, A convenient synthesis of monoamino-s-triazines in high yield is the reaction of 2-phenoxy-s-triazine (319) with ammonia or aliphatic amines (30-70°) or with aniline (120°). Triphenoxy- -triazine (320) reacts with all classes of amines without side-reactions... 

The kinetics of the amination of 2-phenoxy-l,3,5-triazine with piperidine was investigated. Instead of the acid autocatalysis (Section 11), a cyclic mechanism is suggested in which a second piperidine, or much more effectively, valerolactam, acts as a catalyst for the amination (75AJI85I). Similar kinetic results are obtained with 3-phenoxyquinazoline (82G167) and 5-methyl-5-phenoxyquinazoline (85JPR865). 

Kaminski has noted that partial substitution of chlorine atoms in TCT 3 by methoxy or phenoxy groups changes the course of the reaction with carboxylic acids <1985TL2901>. In fact, instead of the expected acyl chlorides, the reaction between 2-chloro-4,6-dialkoxy-[l,3,5]-triazine 295 and carboxylic acids gave highly reactive 2-acyloxy-4,6-dialkoxy-[l,3,5]-triazine 296, which, under further treatment with amines, alcohols, and carboxylic acid anions, afforded amides, esters, and anhydrides, respectively (Scheme 57). 

A study with environmental samples was performed analyzing 26 non-acidic (e.g. organophosphorus, carbamate, triazine, anilide, N-substituted amine and phenylurea type) and 13 acidic (urea and phenoxy acid type) target pesticides simultaneously by ESI-LC-MS with recoveries of about 80% [500]. Drinking, ground and... 

In a study covering a wide range of polar and acidic pesticides deethylatrazine and atrazine besides anilide, phenoxy acid, phenylurea, carbamates and other types of specific pesticides in river water were determined by ESI-LC-MS and MS/MS. Recoveries, depending on preconcentration steps, obtained with different SPE materials (PLRS-S, Hyshere-1, LiChrolut EN and Isolute ENV -i-) and at different pH values were reported [502]. Sixteen of the most widely used pesticides in Southern Italy were monitored in surface water samples taken in the Calabria region. Triazines were determined quantitatively by LC-UV and ESI-LC-MS(-i-) and were confirmed by MS [537]. In another study the simultaneous determination of 26 non-acidic (base and neutral e.g. triazine, carbamate, anilide, N-substituted amine, urea and organophosphorus type) and 13 acidic (sulfuron and phenoxy acid type) pesticides in natural waters was performed using ESI-LC-MS. Recoveries... 

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