Triazine compounds

The half-lives for these four compounds taken from the literature allowed the estimation of the Four reaction rates necessai to model their degradation [18], As a first approximation, the rate of hydrolysis of the C-Cl bond of all Four, -triazine compounds was assumed to be the same and to be 5.0 x 10 s on the basis of literature precedence. This approximation seems reasonable as the four structures differ only in the alkyl groups at a site quite remote from the C-CI bond. Furthermore, among the Four reaction steps hydrolysis is the slowest anyway. 

Table 2 Chemical and physical data for commercially important triazine compound (from Refs. 3-5)...

A plefhora of methods developed for the determination of triazine compounds in water, soil, crops, biological fluids, etc., have been reported in the literature, and several excellent reviews are available for the interested reader. " More method papers are published on the determination of triazines in water than for all other sample matrices combined (water > soil > crop). The majority of the water method reports relate to the determination of parent triazine compounds plus compounds from one or more other chemical classes of pesticides (e.g., phenoxy acids, carbamates, pheny-lureas, acetanilides, acetamides, organophosphorus compounds, etc.) for generalized multi-residue screening or monitoring purposes. Addressed in other more selective... 

The most widely employed techniques for the extraction of water samples for triazine compounds include liquid-liquid extraction (LLE), solid-phase extraction (SPE), and liquid-solid extraction (LSE). Although most reports involving SPE are off-line procedures, there is increasing interest and subsequently increasing numbers of reports regarding on-line SPE, the goal of which is to improve overall productivity and safety. To a lesser extent, solid-phase microextraction (SPME), supercritical fluid extraction (SEE), semi-permeable membrane device (SPMD), and molecularly imprinted polymer (MIP) techniques have been reported. 

Several SPE procedures reported for triazine compounds are summarized in Table 3, and some are applicable to the quantitative extraction of parent triazine... 

Several reported SPE procedures for triazine compounds and some of their degradation products in water are also shown in Table Although the C-18 SPE... 

Pesticides may enter the atmosphere during spray applications of the formulated product, by volatilization, through management practices, via wind-distributed soil particles containing absorbed pesticides, etc. Several analytical methods have been reported over the last 30 years for the determination of pesticides in air, and all involve the passage of known volumes of air for a pre-defined time period through an adsorbent material to trap the desired analytes. These analytes are then extracted, concentrated, and analyzed. A few analytical methods have been reported for the determination of triazine compounds in air in the last decade. 

Early work relied on the use of packed columns, but all modern GC analyses are accomplished using capillary columns with their higher theoretical plate counts and resolution and improved sensitivity. Although a variety of analytical columns have been employed for the GC of triazine compounds, the columns most often used are fused-silica capillary columns coated with 5% phenyl-95% methylpolysiloxane. These nonpolar columns in conjunction with the appropriate temperature and pressure programming and pressure pulse spiking techniques provide excellent separation and sensitivity for the triazine compounds. Typically, columns of 30 m x 0.25-mm i.d. and 0.25-qm film thickness are used of which numerous versions are commercially available (e.g., DB-5, HP-5, SP-5, CP-Sil 8 CB, etc.). Of course, the column selected must be considered in conjunction with the overall design and goals of the particular study. 

The use of collision-induced dissociation (CID) and MS/MS techniques in conjunction with the API interfaces has dramatically impacted the fleld of environmental analysis. These techniques are now preferred for the determination of triazine compounds in water, soil, crops, etc., owing to the significant improvements in selectivity obtained via the monitoring of precursor-product ion pairs and increased sensitivity due to the reduction of chemical noise. 

Wackett LP, Sadowsky MJ, Martinez B et al (2002) Biodegradation of atrazine and related s-triazine compounds from enzymes to field studies. Appl Microbiol Biotechnol 58 39—45... 

The reaction sequence starts from tetrazolyldiazonium salt 42 prepared from aminotetrazole 41 by diazotation. This compound when reacted with arylformylacetonitrile 43 leads to the intermediate formation of the condensation product 44, which easily undergoes ring closure to 45. This tetrazolo[5,l-z][l,2,4]triazine compound, however, forms an equilibrium with the valence bond isomeric azide 46, which can participate in a different ring closure than the reverse route, and yields the tetrazolo[l,5-A][l,2,4]triazine product 47. The reaction was carried out with a series of various aryl derivatives and proceeded in good to excellent yields (68-87%). 

X-Ray investigation of the thiazolo[3,2-A][l,2,4]triazine compound 61 <2001H(55)2189> showed that this compound in the crystal phase exists as a solvate with dimethylformamide (DMF), the amide group is coplanar to the benzene ring (the respective torsion angles are below 4°), and intermolecular hydrogen bonds with the DMF molecules can be found. 

The condensation reaction of the spiro-substituted partially saturated thiazolo[3,2-3][l,2,4]triazine compound 149 was published by Abdel-Rahman et al. <1994PHA729>, as shown in Scheme 22. The transformation was carried out in glacial acetic acid under heating to yield the ethenyl derivative 150 in acceptable yields (55-60%). 

Most of the chemical transformations shown in Scheme 48 were described by an Irani research group during the past decade. All these efforts were aimed at elucidation of synthetic routes to thiazolo[2,3 ][l>2,4]triazine compounds and also to its selenazo analogues. 

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