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PubMed2004

Hollow fiber membrane-protected solid-phase microextraction of triazine herbicides in bovine milk and sewage sludge samples.

A porous polypropylene hollow fiber membrane (HFM)-protected solid-phase microextraction (HFM-SPME) procedure in conjunction with gas chromatography/mass spectrometric analysis for use in the determination of triazine herbicides in bovine milk samples is described. A 65-microm polydimethylsiloxane-divinylbenzne (PDMS-DVB) SPME fiber was protected by an HFM. HFM-SPME experimental parameters such as fiber type, extraction time, extraction temperature and salt concentration were investigated and optimized. The relative standard deviations for the reproducibility of the optimized HFM-SPME method varied from 4.30 to 12.37%. The correlation coefficients of the calibration curves were between 0.9799 and 0.9965 across a concentration range of 0-200 microg l(-1). The method detection limits for triazines in bovine milk were in the range of 0.003-0.013 microg l(-1) and limits of quantification were in the range of 0.006-0.021 microg l(-1). The suitability of HFM-SPME was extended to the analysis of the herbicides in sewage sludge samples. The results demonstrate that HFM-SPME was an efficient pretreatment and enrichment procedure for complex matrices.

Animals↗

PubMed2005

Application of artificial neural networks for prediction of retention factors of triazine herbicides in reversed-phase liquid chromatography.

In this paper a quantitative structure-retention relationship (QSRR) method is used to model reversed-phase high-performance liquid chromatography (HPLC) behaviour of a series of triazine herbicides and their metabolites. Accurate description of the retention factors in terms of four descriptors related to the analytes and to the mobile phase is achieved by means of an artificial neural network (ANN). For comparison, a QSRR model is derived by multilinear regression (MLR). Validation of the two models shows a better ability in prediction of the ANN as compared with the MLR method. A solid-phase extraction (SPE) procedure allowing the simultaneous determination of the five triazinic compounds in groundwater analysis is also presented. The observed recoveries from water samples range between 85 and 100% for ng/ml concentration levels of all analytes.

Chromatography, High Pressure Liquid↗

PubMed2005

Determination of triazines and dealkylated and hydroxylated metabolites in river water using a propazine-imprinted polymer.

A molecularly imprinted polymer (MIP) obtained by precipitation polymerisation using propazine as template has been employed as sorbent for the solid phase extraction of triazines and some of their hydroxylated and dealkylated metabolites from river water. Three configurations were studied: (a) use of the propazine-MIP as a selective sorbent for the extraction of triazines directly from water; (b) use of mixtures of LiChrolut EN (a polymeric sorbent of styrene divinylbenzene) and propazine-MIP as sorbent, and (c) use of propazine-MIP as a clean-up sorbent for organic extracts obtained in a prior SPE procedure with LiChrolut EN. The former two configurations imply that the analytes pass through the propazine-MIP in aqueous medium, whereas in the latter case the analytes percolate through the propazine-MIP in an organic medium coming from the previous SPE step. Different types of water were tested to assess matrix effects. The analytical characteristics of the three configurations were evaluated.

Alkylation↗

PubMed2006

Interaction of novel condensed triazine derivatives with central and peripheral type benzodiazepine receptors: synthesis, in vitro pharmacology and modelling.

Structurally related sets of triazino-quinoline, triazino-isoquinoline and pyrido-triazine derivatives were synthesised and their binding interactions with central (CBR)- and peripheral-type (PBR) benzodiazepine binding sites have been characterised. Of 33 compounds tested, a new compound, 2-(4-methylphenyl)-3H- [1,2,4] triazino [2, 3-a] quinolin-3-one (1 g) showed the lowest CBR binding inhibition constant (K(i) = 42 +/- 9 nM) and the highest CBR over PBR selectivity (>1300). All but the 4-methylphenyl (1 g) structural modifications decreased the affinity and selectivity of the parent compound, 2-phenyl-3H- [1,2,4]triazino[2,3-a]quinolin-3-one (1d) (K(i) = 69 +/- 9 nM, selectivity >890). Molecular interactions between selected ligands (standards and triazine derivatives) and alpha(1)gamma(2) subunit-interface residues in a GABA(A) receptor extracellular domain homology model have been calculated. Comparing data with calculations confirmed hydrogen bonding to gamma(2)Thr142 and hydrophobic interaction with alpha(1)His101 as being essential for high-affinity CBR binding.

Animals↗

PubMed2005

Synthesis and antiamoebic activity of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4] triazin-4-yl thiosemicarbazide derivatives.

A series of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4]triazin-4-yl thiosemicarbazide derivatives 3-22 were prepared and evaluated in vitro against HM1:1MSS strain of Entamoeba histolytica, to identify the compounds for antiamoebic activity. They exhibited antiamoebic activity in the range (IC50=0.81-7.31microM). The results were compared to the activity of known drug metronidazole. It is inferred from the in vitro studies that the compounds 10, 11, 17 and 18 were found to be significantly better inhibitors of E. histolytica since IC50 values in the muM range elicited by these compounds are much lower than metronidazole. Besides, compounds 11 and 17 have shown the most promising antiamoebic activity (IC50=0.81microM of 11, IC50=0.84 microM of 17 versus IC50=1.81microM of metronidazole). The study suggests the possibility of developing triazine analogues as potential drug candidates for antiamoebic activity.

Amebicides↗

PubMed2005

Seasonal exposures to triazine and other pesticides in surface waters in the western Highveld corn-production region in South Africa.

The objective of this study was to characterize concentrations of atrazine, terbuthylazine, and other pesticides in amphibian habitats in surface waters of a corn-production area of the western Highveld region (North-West Province) of South Africa. The study was conducted from November 2001 to June 2002, coinciding with the corn-production season. Pesticide residues were measured at regular intervals in surface water from eight ponds, three in a non-corn-growing area (NCGA) and five within the corn-growing area (CGA). Measured atrazine concentrations differed significantly among sites and between samples. In the five CGA sites, the maximum atrazine concentrations measured during the study ranged from 1.2 to 9.3 microg/L. Although no atrazine was recorded as being applied in the catchment of the three NCGA sites, maximum concentrations from 0.39 to 0.84 microg/L were measured during the study, possibly as a result of atmospheric transport. Maximum measured concentrations of terbuthylazine ranged from 1.22 to 2.1 microg/L in the NCGA sites and from 1.04 to 4.1 microg/L in the CGA sites. The source of terbuthylazine in the NCGA sites may have been in use other than in corn. The triazine degradation products, deisopropylatrazine (DIA) and deethylatrazine (DEA) and diaminochlorotriazine (DACT) were also found in water from both the CGA and NCGA sites. Concentrations of DIA were > or = 1 microg/L throughout the season, while DEA concentrations were mostly <0.5 microg/L before planting but increased after planting and application of herbicides to concentrations >2 microg/L in some locations. Concentrations of DACT were highly variable (LOD to 8 microg/L) both before and after planting and application, suggesting that they resulted from historical use of triazines in the area. Other herbicides such as simazine and acetochlor were only detected infrequently and pesticides such as S-metolachlor, cypermethrin, monocrotophos, and terbuphos, known to be used in the CGA, were not detected in any of the samples. Because of dilution by higher than normal rainfall in the study period, these concentrations may not be predictive of those in years of normal rainfall.

Agriculture↗

PubMed2005

Identification of a new Irgarol-1051 related s-triazine species in coastal waters.

A previously unknown s-triazine species present in commercially available Irgarol-1051, a booster biocide additive in copper-based antifouling paints for the replacement of organotin-based antifoulants, has been identified in the coastal aquatic environment. After careful isolation, purification and characterization by high resolution MS-MS and (1)H NMR, the molecular structure of that unknown species is found to be N,N'-di-tert-butyl-6-methylthiol-s-triazine-2,4-diamine (designated as M3). Levels of Irgarol-1051, its major degradation product (M1) and the newly identified M3 in the coastal waters of Hong Kong, one of the world's busiest ports located in the southern coast of China, were monitored by SPME-GC-MS and SPME-GC-FID. Water samples from five locations within Hong Kong waters were analysed and the levels of Irgarol-1051, M1 and M3 were found to be 0.1-1.6 microg l(-1), 36.8-259.0 microg l(-1) and 0.03-0.39 microg l(-1), respectively. Our results indicate that M3 is relatively stable against photo- and bio-degradation and may pose considerable risk to primary producer communities in the coastal marine environment.

Animals↗

PubMed2006

LC-ESI-MS/MS determination of phenylurea and triazine herbicides and their dealkylated degradation products in oysters.

A method was developed for the determination of several phenylurea and triazine herbicides and their transformation products in oysters at the low microg/kg level. Pressurised liquid extraction (PLE) of lyophilisated samples had required successive SPE combined with a liquid/liquid extraction to provide relatively clean extracts for the determination in LC-MS/MS. This procedure was validated according to the 2002/657/EC analytical decision. Efficiency of the analytical method led to confirmatory CCalpha values ranging from 0.1 to 14 microg/kg with an R.S.D. value ranging from 14% to 66% and a recovery yield ranging from 32% to 46% for phenylureas and from 29% to 75% for triazines.

Animals↗

PubMed2000

Solid-phase extraction with a dibutylmelamine-imprinted polymer as triazine herbicide-selective sorbent.

Triazine herbicide-selective polymer spheres were prepared by molecular imprinting using dibutylmelamine (DBM) as a template in suspension polymerization, and were utilized in solid-phase extraction (SPE) of atrazine. Atrazine-selective SPE was successfully demonstrated with a recovery of ca. 97% and an enrichment factor of 50, proving the good aptitude of DBM as the template species for developing a specific sorbent for triazine herbicides. It is also noteworthy that DBM-imprinted polymers have no possibility of disturbance in agrochemical analyses even if DBM remained in the polymer, which may occur by insufficient washing at the stage of removing the template to yield the binding sites, increasing the availability of imprinted polymers for practical applications.

Chemistry Techniques, Analytical↗

PubMed2001

Development and application of immunoaffinity chromatography for the determination of the triazinic biocides in seawater.

The development of an immunoaffinity chromatography (IAC) procedure for the selective extraction of the anti-fouling agent Irgarol 1051 [2-(tert.-butylamino)-4-(cyclopropylamino)-6-(methylthio)-1,3,5-triazine] from seawater is described. The anti-Irgarol 1051 antibodies were covalently bound to agarose-based beads support. IAC column capacities were higher than 400 ng and ethanol-water (70:30) was selected as eluting mixture. After percolation of 250 ml of water sample containing Irgarol 1051 at environmental levels (ng l(-1) ), the breakthrough volume was still not achieved. Other triazine herbicides percolated through the IAC column showed good recoveries. Thus, this IAC procedure may be useful to extract related compounds. The developed IAC column was applied to real seawater samples and compared with RP-C18 cartridges. The limit of detection (LOD) reached by using the IAC procedure was twenty times lower than the LOD achieved by the RP-C 18 cartridges using the same detection system. Irgarol 1051 was detected at ng l(-1) levels in the Barcelona marina (northwestern Mediterranean Sea). An acceptable correlation between enzyme-linked immunosorbent assay and gas chromatography with nitrogen-phosphorus detection was observed, thus analysis of Irgarol 1051 can be performed by either one of the methods. In this work, further confirmation of the analyte identity for real samples was accomplished by gas chromatography-electron impact mass spectrometry.

Chromatography, Affinity↗

PubMed1984

Purification of alpha 1-proteinase inhibitor by triazine dye affinity chromatography, ion-exchange chromatography and gel filtration on Fractogel TSK.

The purification of plasma proteins by affinity chromatography on triazine dye matrices can be optimised with regard to the triazine dye used as a group-specific ligand. A comparison by electrophoretic and immunological means of the results of affinity chromatography with human plasma on Fractogel TSK-Blue and Fractogel TSK-Red demonstrated that the Procion Red HE-3B-containing gel was able to adsorb more plasma constituents than the Cibacron Blue F3-GA gel. The preparation of alpha 1-proteinase inhibitor obtained after chromatography on Fractogel TSK-Red showed a higher degree of purity and could easily be further purified by ion-exchange chromatography on Fractogel TSK DEAE-650 and gel filtration on Fractogel TSK HW 55, without significant loss of biological activity.

Chromatography, Affinity↗

PubMed2003

Determination of triazines in soil by microwave-assisted extraction followed by solid-phase microextraction and gas chromatography-mass spectrometry.

A method for determining triazine herbicides in soil samples that combines microwave-assisted extraction with solid-phase microextraction is described. Water containing 1% methanol was employed as extractant. The parameters of solid-phase microextraction and microwave-assisted extraction were investigated. In solid-phase microextraction, particular attention was paid to the negative effect of salt on fiber stability. Our experiments showed that this effect could be effectively reduced by simply washing the fiber with deionized water. The selected triazines could be efficiently extracted by the aqueous extractant at 105 degrees C for 3 min, with 80% output of maximum power (1,200 W). The extraction procedure provided good precision (<7%) and recoveries (76.1-87.2%). The limits of detection were in the range 2-4 microg/kg. Compared with conventional liquid extraction, microwave-assisted extraction-solid-phase microextraction was more efficient, accurate and faster, and used a very small amount of organic solvent (only 250 microL methanol). The extraction of aged spiked soil samples indicated that, although the recoveries were lower than those of freshly spiked samples, they were nevertheless satisfactory for the quantitative analysis of real-world samples.

Gas Chromatography-Mass Spectrometry↗

PubMed2003

Design of chiral monochloro-s-triazine reagents for the liquid chromatographic separation of amino acid enantiomers.

A series of chiral derivatizing reagents (CDRs) was synthesized by nucleophilic replacement of one chlorine atom in cyanuric chloride (2,4,6-trichloro-1,3,5-triazine; s-triazine) by alkoxy (methoxy, butoxy, 1,1,1-trifluoroethoxy) or aryloxy groups (phenoxy, nitrophenoxy, phenylphenoxy, 4-methylcoumaryloxy), and displacement of a second chlorine by L-alanine amide, L-phenylalanine amide, L-proline tert.-butyl ester, or Boc-L-lysine tert.-butyl ester. Further, CDRs were investigated in which two chlorine atoms in cyanuric chloride were substituted consecutively by L-valine amide and L-phenylalanine amide. The resulting CDRs having a remaining reactive chlorine were tested for their capability of derivatizing DL-amino acids followed by liquid chromatographic separation of the resulting diastereomers.

Amino Acids↗

PubMed2003

Optimisation of a solid-phase microextraction procedure for the determination of triazines in water with gas chromatography-mass spectrometry detection.

A procedure based on solid-phase microextraction (SPME) and gas chromatography-mass spectrometry, operating in the chemical ionisation mode, was developed and optimised in order to determine 10 triazines in water samples. Five different SPME fibers available for analysis [polydimethylsiloxane (PDMS) 100 microm, polyacrylate (PA) 80 microm, PDMS-divinylbenzene (DVB) 65 microm, Carbowax (CW)-DVB 65 microm, and Carboxen (CAR)-PDMS 75 microm] were tested, and PDMS-DVB was selected. To enhance the sensitivity of the SPME, variables affecting adsorption and desorption steps such as temperature, time, pH and ionic strength of the solution were optimised. Detection limits obtained were ranged between 2 and 17 ng l(-1), and precision values were below 8% for the selected PDMS-DVB fiber. The optimised method was applied to real water samples and no triazines were detected.

Gas Chromatography-Mass Spectrometry↗

PubMed1999

On-line coupling of immunoaffinity-based solid-phase extraction and gas chromatography for the determination of s-triazines in aqueous samples.

The potential of immunoaffinity-based solid-phase extraction (IASPE) coupled on-line to gas chromatography (GC) for the determination of micropollutants was studied with emphasis on the interfacing of the immunoaffinity-based SPE and GC parts of the system. The cartridge containing the immobilized antibodies was coupled to the gas chromatograph via a reversed-phase cartridge (copolymer sorbent). After trace enrichment of the analytes on the immunoaffinity cartridge, they were desorbed and recollected on the reversed-phase cartridge by means of an acidic buffer. After clean-up and drying with nitrogen, desorption and transfer to the GC was done with ethyl acetate via an on-column interface in the partially concurrent solvent evaporation mode. The antibodies used in the immunoaffinity cartridge were raised against atrazine; several s-triazines were used as test compounds. Triazines that were structurally similar to atrazine, showed quantitative recovery. As an application, immunoaffinity SPE-GC was used for the analysis of river and waste water and orange juice. The selectivity of the system was such that non-selective flame ionization detection (FID) could be used to detect the analytes of interest in these complex matrices. The detection limits for 10-ml water samples were 15-25 ng/l for FID and about 1.5 ng/l for the nitrogen-phosphorus detection.

Atrazine↗

PubMed2000

Determination of triazines in soil leachates by solid-phase microextraction coupled to gas chromatography-mass spectrometry.

A solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS) method was developed for the evaluation of the leachability order of selected triazines (propazine, terbuthylazine, sebuthylazine, ametryn, prometryn and terbutryn) in soil/sediment samples (organic carbon content ranging from 0.19 to 0.42%), analysing fractions collected from a soil packed microcolumn elution experiments. The procedure is fast, simple, highly sensitive and solvent free. SPME-GC-MS was also employed for the quantitative determination of triazines in the soil leachate, since the method showed good recovery yield. Detection limits were always better than 1 ng ml(-1). The method was tested on a contaminated landfill top soil. Prometryn and ametryn were identified through their MS spectra and then quantified. Terbuthylazine was used to assess recovery. Results compared well with those obtained by solvent extraction followed by HPLC-UV detection.

Gas Chromatography-Mass Spectrometry↗

PubMed2000

Trace-level determination of triazines and several degradation products in environmental waters by disk solid-phase extraction and micellar electrokinetic chromatography.

An analytical method combining disk solid-phase extraction with micellar electrokinetic chromatography has been developed for the determination of atrazine, simazine, hydroxyatrazine, deisopropylatrazine, deethylatrazine, propazine and prometryn in water samples. The influence of the buffer and sodium dodecyl sulfate (SDS) concentration, pH and organic modifier on the separation has been studied. Baseline separation of the seven triazines was achieved under the following conditions: 10 mM borate buffer, 60 mM SDS, 20% methanol and pH 9.2. C18-bonded silica and poly(styrene-divinylbenzene) (PS-DVB) disks were evaluated for solid-phase extraction of the selected pesticides (11 of water sample). Using two PS-DVB disks, quantitative recoveries were obtained for all pesticides tested. The method was successfully applied for the determination of the seven triazines in drinking and well water at the 0.1 microg l(-1) and 0.5 microg l(-1) concentration levels, respectively. The detection limits for these analytes using the proposed analytical method were within the 0.02-0.06 microg l(-1) range in drinking water and the 0.06-0.30 microg l(-1) range in well water.

Buffers↗

PubMed2002

Effects of antifouling paint components (TBTO, copper and triazine) on the early development of embryos in cod (Gadus morhua L.).

To assess the risk of antifoulant use to the commercially important cod (Gadus morhua L.), fertilised cod eggs were exposed to triazine, copper and TBTO singly or combined in laboratory tests with running seawater. At the highest tested concentrations (11.5 microg Cu l(-1); 5 microg TBTO l(-1)) larval mortality was increased. The highest concentration of triazine (40 microg l(-1)) did not cause any significant mortality. Fertilised eggs that had been exposed to all the three chemicals singly for five days showed a higher buoyancy than the controls. No synergistic or antagonistic effects were indicated. Embryos/larvae exposed to 0.004-0.8 microg TBTO l(-1) did not show any changed respiration compared to the controls after hatching. It is concluded that existing known field concentrations of the three antifoulants are hardly expected to cause detectable effects on fish embryonic/larval development.

Animals↗