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PubMedDate not supplied

Production and characterization of monoclonal antibodies specific to atrazine group compounds: effects of coating ligand structure on the variation of sensitivity and specificity.

Hybridoma cells were prepared by immunizing mice with carboxylic derivatives of atrazine conjugate to bovine serum albumin. After the screening of culture supernatant of hybridomas, five cell lines producing monoclonal antibodies were established and 1.8-5.3 ml of ascitic fluid per mouse was obtained from each cell line. The protein A affinity purification yielded 0.35-0.65 mg per ml of ascitic fluid from each cell line. The characterization studies in terms of sensitivity and specificity indicate that MAb 2F9 and MAb 4B9 showed the best responses with atrazine and its group of ametryne and cyanazine, using microtiter plate coated with simazine derivative of 6-amino hexanoic acid; no cross-reactivity was shown with simazine and cyanuric chloride.

Animals↗

PubMed2005

Elimination of pesticides in olive oil by refining using bleaching and deodorization.

The effects of the processing steps on some pesticides during physical refining of olive oil were determined. Oil samples were spiked with four types of pesticides, i.e. endosulfan (alpha-endosulfan, beta-endosulfan and endosulfan sulphate), simazine, oxifluorfen and diflufenican, and subjected to physical refining (bleaching and deodorization). The removal of contaminants by bleaching earths was compared using five types of commercial earths. Deodorization assays under laboratory (10 kg) and discontinuous pilot plant (200 kg) conditions at different temperatures and treatment times were carried out. Bleaching seemed effective only for the elimination of simazine. For removal of the other pesticides tested, a physical refining treatment was required at 240 degrees C in the deodorizing stage for different periods (1 h for diflufenican, oxifluorfen and alpha-endosulfan, 2 h for beta-endosulfan and 3 h for endosulfan sulphate).

Food Analysis↗

PubMed2006

Monitoring of triazine and phenylurea herbicides in the surface waters of Greece.

A large-scale study was implemented to monitor triazine and phenylurea herbicides in the main surface water bodies of continental Greece from October 1998 to September 1999. Samples from 10 rivers and 7 lakes were analyzed for the presence of five triazine (atrazine, cyanazine, prometryne, simazine, terbuthylazine) and five phenylurea (chlorotoluron, diuron, linuron, metobromuron, monolinuron) herbicides. The samples were extracted with C18 cartridges and analyzed by high-performance liquid chromatography-diode array detection (HPLC-DAD). The most frequently detected herbicides were atrazine, followed by prometryne, cyanazine, and simazine. The concentrations of the compounds were generally low (< 0.78 micro g/L) and are not considered harmful for the freshwater ecosystem. Most of the positive samples were taken from the water bodies of northern Greece where agricultural activity is more intense.

Chromatography, High Pressure Liquid↗

PubMed2001

Organic pollutants in surface waters from Portugal using chemometric interpretation.

Surface water samples from 45 sampling points across Portugal have been analyzed monthly by automated Solid Phase Extraction (SPE) and Gas Chromatography-Mass Spectrometry (GC/MS) in SIM and SCAN modes. Sampling was carried out during a period of six months (April-September, 1999), in order to determine the levels of contamination of 72 organic compounds mainly selected from the EC Council Directive list (CEC 76/464/EEC). Atrazine, simazine, deethylatrazine, alachlor, metolachlor, Irgarol, terbuthylazine, tributhylphosphate, 2,4,6-trichlorophenol, 2-chlorophenol, 3-chlorophenol, pentachlorophenol, dimethoate, lindane, linuron, propanil, o,p'-DDD, o,p'-DDT, o,p'-DDE and malathion were the main detected compounds. Although Irgarol, terbuthylazine, deethylatrazine and deisopropylatrazine are not listed in the EC Directive, these herbicides and transformation products are currently in use and they were also included in the monitoring program and detected at some sites. Fifty-nine percent of the samples were below 0.1 microg l(-1), the detection limit required the EEC Drinking Water Directive (DWD). Some compounds were detected at values higher than the DWD, e.g. atrazine (2.7 microg l(-1)) and alachlor (5.43 microg l(-1)) in April. Simazine was also present with a high value (2.3 microg l(-1)) in September. Tributhylphosphate (5.40 microg l(-1)) and 2,4,6-trichlorophenol (2.31 microg l(-1)) were also found at high concentrations near industrial sites. Chemometric interpretation of the more representative contaminants was performed by means of Principal Component Analysis, allowing the resolution of the more relevant contamination sources and the description of their temporal and spatial (geographical) distributions.

Environmental Monitoring↗

PubMed2003

Degradation of soil environment in the post-flooding area: content of polycyclic aromatic hydrocarbons (PAHs) and s-triazine herbicides.

Impacts of flooding on the soil environment with regard to soil pollution with polycyclic aromatic hydrocarbons and s-triazine (cyanazine, simazine, atriazine, propazine, prometryn) herbicides have been evaluated. No clear differences in the sum of the PAHs content were observed in the present studies. Only changes in the levels of individual PAHs were noted. In soils covered with flooding both at a depth of 0-20 and 20-40 high molecular weight PAHs were predominant (especially mutagenic and carcinogenic 5-rings PAHs) whereas in non-flooded areas, 2- and 3-rings PAHs constituted over 80%. In the case of s-triazine herbicides, no influence of flooding on the changes in their content in agriculturally used soils was noted. On the other hand, clearly lower levels of cyanazine, simazine and atriazine were not in the flooded forest soil as compared to the non-flooded forest soil.

Biodegradation, Environmental↗

PubMed2003

Prostate cancer risk in California farm workers.

Previous studies have evaluated prostate cancer in farm-working populations and most, although not all, have found an elevated risk of this cancer in farmers and farm workers. Specific occupational risk factors have not been identified. A nested case-control study of prostate cancer was conducted within a large cohort of a predominantly Hispanic labor union in California, the United Farm Workers of America. By conducting an electronic record linkage between a roster of the union members and the California Cancer Registry for the years 1988 through 1999, newly diagnosed cases of prostate cancer were identified within the union. Age-matched controls were randomly selected from the remainder of the cancer-free cohort. Risk for prostate cancer was examined by examining the type of crops and commodities cultivated by the farm workers as well as by the date of first union activity and duration of union affiliation. In addition, the risk of prostate cancer was evaluated in association with use of several pesticides recorded by the California Department of Pesticide Regulation. Between 1988 and 1999, 222 newly diagnosed prostate cancer cases were identified for analysis and 1110 age-matched controls were selected. The risk of prostate cancer was not associated with patterns of employment in any crop/commodity. Increasing duration of union affiliation was associated with decreasing prostate cancer risk. Although risk was not associated with total pounds of pesticides applied in the years and counties where farm workers were employed, risk was increased with specific chemicals, including simazine, lindane, and heptachlor, and suggestive increases were observed with dichlorvos and methyl bromide. We concluded that Hispanic farm workers with relatively high levels of exposure to organochlorine pesticides (lindane and hepatachlor), organophosphate pesticides (dichlorvos), fumigants (methyl bromide), or triazine herbicides (simazine) experienced elevated risk of prostate cancer compared to workers with lower levels of exposure.

Aged↗

PubMed2005

Enzymatic activity, osmotic stress and degradation of pesticide mixtures in soil extract liquid broth inoculated with Phanerochaete chrysosporium and Trametes versicolor.

In this study we examined the extracellular enzymatic activity of two white rot fungi (Phanerochaete chrysosporium and Trametes versicolor) in a soil extract broth in relation to differential degradation of a mixture of different concentrations (0-30 p.p.m.) of simazine, dieldrin and trifluralin under different osmotic stress (-0.7 and -2.8 MPa) and quantified enzyme production, relevant to P and N release (phosphomonoesterase, protease), carbon cycling (beta-glucosidase, cellulase) and laccase activity, involved in lignin degradation. Our results suggest that T. versicolor and P. chrysosporium have the ability to degrade different groups of pesticides, supported by the capacity for expression of a range of extracellular enzymes at both -0.7 and -2.8 MPa water potential. Phanerochaete chrysosporium was able to degrade this mixture of pesticides independently of laccase activity. In soil extract, T. versicolor was able to produce the same range of enzymes as P. chrysoporium plus laccase, even in the presence of 30 p.p.m. of the pesticide mixture. Complete degradation of dieldrin and trifluralin was observed, while about 80% of the simazine was degraded regardless of osmotic stress treatment in a nutritionally poor soil extract broth. The capacity of tolerance and degradation of high concentrations of mixtures of pesticides and production of a range of enzymes, even under osmotic stress, suggest potential bioremediation applications.

Basidiomycota↗

PubMed1994

Purification and Characterization of an Inducible s-Triazine Hydrolase from Rhodococcus corallinus NRRL B-15444R.

The widespread use and relative persistence of s-triazine compounds such as atrazine and simazine have led to increasing concern about environmental contamination by these compounds. Few microbial isolates capable of transforming substituted s-triazines have been identified. Rhodococcus corallinus NRRL B-15444 has previously been shown to possess a hydrolase activity that is responsible for the dechlorination of the triazine compounds deethylsimazine (6-chloro-N-ethyl-1,3,5-triazine-2,4-diamine) (CEAT) and deethylatrazine (6-chloro-N-isopropyl-1,3,5-triazine-2,4-diamine) (CIAT). The enzyme responsible for this activity was purified and shown to be composed of four identical subunits of 54,000 Da. Kinetic experiments revealed that the purified enzyme is also capable of deaminating the structurally related s-triazine compounds melamine (2,4,6-triamino-1,3,5-triazine) (AAAT) and CAAT (2-chloro-4,6-diamino-1,3,5-triazine), as well as the pyrimidine compounds 2,4,6-triaminopyrimidine (AAAP) and 4-chloro-2,6-diaminopyrimidine (CAAP). The triazine herbicides atrazine and simazine inhibit the hydrolytic activities of the enzyme but are not substrates. Induction experiments demonstrate that triazine hydrolytic activity is inducible and that this activity rises approximately 20-fold during induction.

Journal Article↗

PubMed2002

Community exposures to airborne agricultural pesticides in California: ranking of inhalation risks.

We assessed inhalation risks to California communities from airborne agricultural pesticides by probability distribution analysis using ambient air data provided by the California Air Resources Board and the California Department of Pesticide Regulation. The pesticides evaluated include chloropicrin, chlorothalonil, chlorpyrifos, S,S,S-tributyl phosphorotrithioate, diazinon, 1,3-dichloropropene, dichlorvos (naled breakdown product), endosulfan, eptam, methidathion, methyl bromide, methyl isothiocyanate (MITC; metam sodium breakdown product), molinate, propargite, and simazine. Risks were estimated for the median and 75th and 95th percentiles of probability (50, 25, and 5% of the exposed populations). Exposure estimates greater than or equal to noncancer reference values occurred for 50% of the exposed populations (adults and children) for MITC subchronic and chronic exposures, methyl bromide subchronic exposures (year 2000 monitoring), and 1,3-dichloropropene subchronic exposures (1990 monitoring). Short-term chlorpyrifos exposure estimates exceeded the acute reference value for 50% of children (not adults) in the exposed population. Noncancer risks were uniformly higher for children due to a proportionately greater inhalation rate-to-body weight ratio compared to adults and other factors. Target health effects of potential concern for these exposures include neurologic effects (methyl bromide and chlorpyrifos) and respiratory effects (1,3-dichloropropene and MITC). The lowest noncancer risks occurred for simazine and chlorothalonil. Lifetime cancer risks of one-in-a-million or greater were estimated for 50% of the exposed population for 1,3-dichloropropene (1990 monitoring) and 25% of the exposed populations for methidathion and molinate. Pesticide vapor pressure was found to be a better predictor of inhalation risk compared to other methods of ranking pesticides as potential toxic air contaminants.

Adolescent↗

PubMed2003

Growth and nitrite and nitrous oxide accumulation of Paracoccus denitrificans ATCC 19367 in the presence of selected pesticides.

The effects of the application of eight pesticides (aldrin, lindane, dimetoate, methylparathion, methidation, atrazine, simazine, and captan) on growth, respiratory activity (as CO2 production), denitrifying activity (as N2O released), and nitrite accumulation in the culture medium by Paracoccus denitrificans strain ATCC 19367 were studied. The fungicide captan totally inhibited growth and biological activity of P. denitrificans, while the rest of the tested pesticides delayed the growth and CO2 release of P. denitrificans but did not drastically affect the bacterial growth or respiratory capacity after 96 h of culture. The denitrifying activity of P. denitrificans ATCC 19367 (as N2O released) was negatively affected by all tested pesticides. The release of N2O was strongly inhibited by several organochlorinated and organophosphorated insecticides (aldrin, lindane, dimetoate, and methidation), which led to high accumulation of nitrite in the surrounding medium. Atrazine decreased N2O release after 48 h of culture because of negative effects on growth, and methylparathion and simazine delayed the onset of N2O release by P. denitrificans. These three pesticides reduced the accumulation of NO2- compared to unamended control cultures.

Carbon Dioxide↗

PubMedDate not supplied

Differentiating nonpoint sources of deisopropylatrazine in surface water using discrimination diagrams.

Pesticide degradates account for a significant portion of the pesticide load in surface water. Because pesticides with similar structures may degrade to the same degradate, it is important to distinguish between different sources of parent compounds that have different regulatory and environmental implications. A discrimination diagram, which is a sample plot of chemical data that differentiates between different parent compounds, was used for the first time to distinguish whether sources other than atrazine (6-chloro-N2-ethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine) contributed the chlorinated degradate, deisopropylatrazine (DIA; 6-chloro-N-ethyl-1,3,5-triazine-2,4-diamine) to the Iroquois and Delaware Rivers. The concentration ratio of deisopropylatrazine to deethylatrazine [6-chloro-N-(1-methylethyl)1,3,5-triazine-2,4-diamine], called the D2R, was used to discriminate atrazine as a source of DIA from other parent sources, such as cyanazine (2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropionitrile) and simazine (6-chloro-N,N'-diethyl-1,3,5-triazine-2,4diamine). The ratio of atrazine to cyanazine (ACR) used in conjunction with the D2R showed that after atrazine, cyanazine was the main contributor of DIA in surface water. The D2R also showed that cyanazine, and to a much lesser extent simazine, contributed a considerable amount (approximately 40%) of the DIA that was transported during the flood of the Mississippi River in 1993. The D2R may continue to be a useful discriminator in determining changes in the nonpoint sources of DIA in surface water as cyanazine is currently being removed from the market.

Atrazine↗

PubMed2004

Weed control and persistence of two oxyfluorfen formulations in olive groves under non tillage conditions.

To obtain profitable yields in olive groves, residual preemergence herbicides are applied in October or November before the winter rains, and before the winter annual weeds germinate. Simazine, one of the herbicides most used for weed control in olive groves, has recently been banned. Oxyfluorfen is presented as a good alternative to simazine in olive fields. Experiments were carried out in 2002 and 2003 to evaluate the behaviour of two oxyfluorfen formulations, 2XL and G4F, at 480 g a.i. ha(-1) for three different soil management systems with three replications (1. bare soil; 2. bare soil and grassed buffer strips, chemically controlled and 3. bare soil and grassed buffer strips with controlled mowing; under non tillage conditions in all three cases). The most important species that survived 2XL and G4F treatments was Sagina apetala ARD. Oxyfluorfen residues were evaluated throughout 158 days after the applications. Three soil samples from each plot were collected, mixed and air dried. The herbicide extractions were made with methanol and the residues were analyzed by HPLC. We found no differences between the two formulations, but results showed that recoveries of oxyfluorfen were higher in plots with chemically controlled buffer grassed strips than in the other soil management types.

Agriculture↗

PubMed1996

The inhibition of estrogen receptor-mediated responses by chloro-S-triazine-derived compounds is dependent on estradiol concentration in yeast.

The chloro-S-triazine derived compounds atrazine, atrazine desisopropyl, cyanazine, and simazine are commonly used herbicides. These compounds do not have estrogenic activity in yeast expressing human estrogen receptor (hER) and an estrogen-sensitive reporter. In the presence of a concentration of estradiol (20 nM) that induced maximal reporter activity in yeast, the triazines did not inhibit reporter activity. However, the triazines decreased reporter activity in a dose dependent manner in the presence of a submaximal concentration of estradiol (0.5 nM). The estradiol-dependent activity of a mutant hER lacking the amino terminus was not inhibited by the triazines in yeast. Competition binding assays demonstrated that the triazines displaced radiolabeled estradiol from recombinant hER. These results suggest that the ability of the triazines to inhibit estrogen receptor-mediated responses in yeast occur through their interaction with hER and is dependent on the concentration of estradiol.

Atrazine↗

PubMed1988

Assessment of the mutagenicity of fractions from s-triazine-treated Zea mays.

A water-soluble extract from maize plants exposed to 3 s-triazine herbicides (atrazine, simazine and cyanazine) has been shown to be mutagenic in strain TA100 of Salmonella. No mutagenic activity was observed in any control plant extracts using either water or a variety of organic solvents. Gel permeation studies of the extracts suggest that the mutagen(s) are small molecules (less than 1000 MW). HPLC fractionation suggests that the mutagens formed from each of the 3 herbicides are similar in polarity and water solubility, eluting in a 50/50 water:methanol fraction. Approximately 89% of 14C-labeled HPLC chromatographable metabolites of atrazine were also associated with this fraction, suggesting a close chemical link between a labeled but unidentified metabolite and the mutagenic activity.

Atrazine↗

PubMed2006

Comparison of a non-aqueous capillary electrophoresis method with high performance liquid chromatography for the determination of herbicides and metabolites in water samples.

A method of capillary electrophoresis (CE) for the determination of triazine herbicides and some of their main metabolites in water samples has been developed. The proposed CE method includes an off-line solid-phase extraction (SPE) procedure with LiChrolut EN sorbent coupled to a non-aqueous capillary electrophoresis (NACE) separation with UV detection. The target compounds were the chloro-s-triazines simazine, atrazine, propazine; the methyltio-s-triazines ametryn and prometryn and three main derivatives from the atrazine degradation products; namely, deethylatrazine, deethylhydroxyatrazine and deisopropylhydroxyatrazine. The analytical characteristics of the CE method are reported. The repeatability of the method was studied considering the different steps of the method separately in order to determine the contributions of each step to the total variability of the method. The NACE-UV results are compared with those obtained with a high performance liquid chromatography with UV detection (HPLC-UV) method. The same off-line SPE procedure was applied to both techniques. The results obtained show that both methods afford the same results in the analysis of surface and drinking water samples, with a level of significance regarding the F- and t-tests greater than 0.05 in all the cases. The detection limits in surface water samples were in the 0.04-0.32 microg l(-1) and 0.11-1.2 microg l(-1) ranges for the NACE-UV and HPLC-UV methods, respectively. The recoveries (spiked/found) were significantly 100% in all cases.

Atrazine↗

PubMed2006

Continuous flow microextraction combined with high-performance liquid chromatography for the analysis of pesticides in natural waters.

Continuous flow microextraction (CFME) combined with high-performance liquid chromatography-ultraviolet (HPLC-UV) detection has been applied to the analysis of five widely used pesticides, simazine, fensulfothion, etridiazole, mepronil and bensulide, present at trace levels in water samples. CFME employs a single organic solvent drop positioned at the tip of a polyether ether ketone (PEEK) tubing, which is immersed in a continuous flowing aqueous sample solution in a 0.5-ml glass chamber. The PEEK tubing acts as the organic drop holder and fluid delivery duct. Analytes are partitioned between the organic drop and the bulk sample solution. Important extraction factors including type of solvent, its volume, sample solution flow rate, extraction time, its pH and addition of salt were investigated. All pesticides exhibit good linearity in the investigated concentration range of 25-250 ng ml(-1) with coefficients of determination (R2) ranging from 0.9879 to 0.9999 under the optimized conditions. Detection limits lower than 4 ng ml(-1) were obtained for all analytes. The method was evaluated by analyzing natural water sample collected from a reservoir in Singapore. This study for the first time demonstrated the compatibility of CFME procedure and HPLC separation.

Chromatography, High Pressure Liquid↗

PubMed2006

Source and persistence of pesticides in a semi-confined chalk aquifer of southeast England.

Pesticide contamination in groundwater is an increasing problem that poses a significant long-term threat to water quality. Following the detection of elevated concentrations of diuron in boreholes in a semi-confined chalk aquifer from southeast England, a sampling programme was undertaken. Between 2003 and 2004 diuron was observed in 90% of groundwaters analysed. In 60% of groundwater samples metabolites of diuron were more prevalent than the parent compound. Longer-term (1989-2005) monitoring shows that pollution of the aquifer by atrazine, simazine, and more recently diuron, shows a positive correlation with periods of high groundwater levels. Results from groundwater residence time indicators suggest that the highest diuron concentrations are associated with waters containing the greatest proportion of recent recharge. There is some evidence to indicate that diuron occurrence can be spatially related to areas of urban and industrial development and is probably correlated with amenity usage.

Atrazine↗

PubMed2006

Anthropogenic contaminants as tracers in an urbanizing karst aquifer.

Karst aquifers are uniquely vulnerable to contamination. In the Barton Springs segment of the karstic Edwards aquifer (Texas, U.S.A.), urban contaminants such as pesticides and volatile organic compounds frequently are detected in spring base flow. To determine whether contaminant concentrations change in response to storms, and if they therefore might act as tracers of focused recharge, samples were collected from Barton Springs at closely spaced intervals following three storms. Two herbicides (atrazine and simazine), two insecticides (carbaryl and diazinon), and a solvent (tetrachloroethene) described breakthrough curves over a 1-week period following one or more storms. The breakthrough curves were decomposed into two to five log-normal subcurves, which were interpreted as representing pulses of contaminants moving through the aquifer. Each subcurve could be used in the same way as an artificial tracer to determine travel time to and recovery at the spring. The contaminants have several advantages over artificial tracers: they represent the actual compounds of interest, they are injected essentially simultaneously at several points, and they are injected under those conditions when transport is of the most interest, i.e., following storms. The response of storm discharge, specific conductance, and contaminant loading at the spring depended on initial aquifer flow conditions, which varied from very low (spring discharge of 0.48 m3/s) to high (spring discharge of 2.7 m3/s): concentrations and recovery were the highest when initial aquifer flow conditions were low. This behavior provides information about aquifer structure and the influence of aquifer flow condition on transport properties.

Animals↗