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PubMed2001

Effects of chloro-s-triazine herbicides and metabolites on aromatase activity in various human cell lines and on vitellogenin production in male carp hepatocytes.

We investigated a potential mechanism for the estrogenic properties of three chloro-s-triazine herbicides and six metabolites in vitro in several cell systems. We determined effects on human aromatase (CYP19), the enzyme that converts androgens to estrogens, in H295R (adrenocortical carcinoma), JEG-3 (placental choriocarcinoma), and MCF-7 (breast cancer) cells; we determined effects on estrogen receptor-mediated induction of vitellogenin in primary hepatocyte cultures of adult male carp (Cyprinus carpio). In addition to atrazine, simazine, and propazine, two metabolites--atrazine-desethyl and atrazine-desisopropyl--induced aromatase activity in H295R cells concentration-dependently (0.3-30 microM) and with potencies similar to those of the parent triazines. After a 24-hr exposure to 30 microM of the triazines, an apparent maximum induction of about 2- to 2.5-fold was achieved. The induction responses were confirmed by similar increases in CYP19 mRNA levels, determined by reverse-transcriptase polymerase chain reaction. In JEG-3 cells, where basal aromatase expression is about 15-fold greater than in H295R cells, the induction responses were similar but less pronounced; aromatase expression in MCF-7 cells was neither detectable nor inducible under our culture conditions. The fully dealkylated metabolite atrazine-desethyl-desisopropyl and the three hydroxylated metabolites (2-OH-atrazine-desethyl, -desisopropyl, and -desethyl-desisopropyl) did not induce aromatase activity. None of the triazine herbicides nor their metabolites induced vitellogenin production in male carp hepatocytes; nor did they antagonize the induction of vitellogenin by 100 nM (EC(50) 17beta-estradiol. These findings together with other reports indicate that the estrogenic effects associated with the triazine herbicides in vivo are not estrogen receptor-mediated, but may be explained partly by their ability to induce aromatase in vitro.

Animals↗
PubMed2006

Triazine adsorption by saponite and beidellite clay minerals.

We investigated the sorption of three triazine herbicides (atrazine, simazine, and metribuzin) by saponite and beidellite clay minerals saturated with K+, Cs+, Na+, and Ca2+. Saponite clay sorbed a larger fraction of each pesticide from aqueous solution than did beidellite clay. The lower cation-exchange capacity in saponite compared to that in beidellite presumably results in a less crowded interlayer, with more siloxane surface being available for adsorption. Generally, Cs-saturated clays sorbed more triazines than did clays saturated by K+, Na+, or Ca2+. We attribute this to the smaller hydrated radius of Cs+, which again increases the siloxane surface that is available for sorption. Furthermore, the relatively weak hydration of Cs+ reduces the swelling of clay interlayers, thus making sorption domains less hydrated and more receptive to hydrophobic molecules. The Cs-saponite manifested a sorption of more than 1% atrazine by weight above equilibrium concentrations of 6 mg/L, which to our knowledge is the largest sorption of neutral atrazine from water yet reported for an inorganic sorbent. Molecular dynamics simulations indicate that atrazine interacts both with clay basal planes and with multiple cations in the clay interlayer.

Adsorption↗
PubMed2000

[A noninstrumental Immunoassay based on colloidal dyes].

Detecting labels based on water dispersions of colloidal textile dyes were developed that are useful in various analytical and diagnostic test systems for a simple visual assessment of the assay. Colored water-insoluble particles of dyes were used for the sorptional immobilization of streptavidin on their surface. The resulting streptavidin-dye (STR-DYE) complexes possessed a high visualizing capacity and were used for the combined detection of pesticides (simazine and 2,4-dichlorophenoxyacetic acid) by noninstrumental immunoassay (DYE-comb-assay, competitive dot-immunoassay in the comb format). The detection limits and the duration of our DYE-comb-assay (4 ng/ml, 20-25 min), HRP-comb-assay (competitive dot-immunoassay in the comb format using the enzymic conjugate of STR with horseradish peroxidase) (16 ng/ml), and the traditional competitive ELISA (12-16 ng/ml, 1.5 h) were compared. This DYE-comb-assay is simple enough and can be used under field conditions.

2,4-Dichlorophenoxyacetic Acid↗
PubMed2001

Determination of resistant biotypes of Amaranthus retroflexus L. on triazines.

Considering the fact that since 1966 in our country the mostly produced have been triazine herbicides on the bases of ametryn, simazine, atrazine and prometryn, we have studied resistance of Amaranthus retroflexus from different sites in regard to the above mentioned herbicides. Seed of weed species for which exist-possibility of resistance have been collected from different localities in Vojvodina, such as Backa Palanka, Backi Maglic and Becej. Studies were performed during 1999 and 2000 by whole plant studies (Thurnwachter, 1998) and by petri dish assays (Clay, Underwood, 1989). Plants were treated by range of atrazine rates (Atrazin S-50) including also susceptible, referent population. Results indicate atrazine resistance of Amaranthus retroflexus at Backa Palanka and Backi Maglic sites, which have been treated by triazine herbicides in many years lasting period.

Amaranthus↗
PubMed2002

[Analysis of carbaryl and other pesticides by capillary electrophoresis].

Five pesticides, i.e. carbaryl, simazine, atrazine, arnetryne and prometryn were separated by capillary electrophoresis technique. The effects of experimental parameters including pH, the concentration of surfactant and organic modifier on the separation were investigated. From the experiments, we found the optimum electrophoretic conditions were as follows: 20 mmol/L borate-50 mmol/L sodium dodecyl sulfate-10% methanol (volume fraction) as the running buffer (pH 9.2), applied voltage of 25 kV, detection wavelength of 225 nm. Under the optimum conditions, baseline-separation of each component has been obtained using anionic surfactant for micellar electrokinetic chromatography. The results indicated that the calibration curve of carbaryl was linear in the range of concentrations 30 mg/L-200 mg/L. This method has been applied to the determination of real sample with satisfactory results obtained, and the recovery of carbaryl was 93.4%-101.3%, and the relative standard deviation of peak area was 2.59%.

Atrazine↗
PubMed1990

[The toxicity of a prometryne/simazine combination in the lactation stage of rats].

The postnatal effect of a combination of Prometryne and Simazine was analyzed in rats. Lactating rats were administered from 5 through 10 d pp. The effect on rat pups were characterized by reflex development, behavioural toxicological tests, and selected biochemical investigations. Distinct effects were observed on body weight, neuro-muscular maturation, and somatic development. There were also significant differences in the content of C-reactive protein and the number of white blood cells.

Animals↗
PubMed1980

[Chemical weed control in the cropping of medicinal plants. Part 1: Valerian (Valeriana officinalis L.) (author's transl)].

More than 40 herbicides have been tested in field trials with valerian over a period of several years. The following herbicidies have proved best suited: chloropham for application in autumn after planting, metobromurone for spraying in the early spring at the commencement of sprouting, nitrofen or a nitrofen-simazine compound preparation for application in May. The utilization of a sequence of herbicides led to a 90% reduction of the weed cover and a 65% reduction of the manual work needed for weed control. The yield and the essential oil and valepotriate contents of valerian were not impaired. The results from residue analyses are presented.

Chlorpropham↗
PubMed1996

Assessing the estrogenic and dioxin-like activities of chemicals and complex mixtures using in vitro recombinant receptor-reporter gene assays.

In vitro recombinant receptor-reporter gene assays have been used to assess and rank the potency of chemicals and complex mixtures suspected of possessing estrogen and (or) aryl hydrocarbon receptor (AhR) mediated activity. The environmental estrogen (E2) bioassay consists of a Gal4-human estrogen receptor chimeric construct (Gal4-HEGO) and a Gal4-regulated luciferase reporter gene (17m5-G-Luc) that have been stably integrated into HeLa cells. The assay exhibits 10-fold induction in luciferase reporter gene activity following treatment with 1 nM 17 beta-estradiol and has a detection limit of approximately 5 pg of 17 beta-estradiol/mL. The AhR bioassay uses Hepa 1c1c7 wild-type cells transiently transfected with a dioxin response element regulated luciferase reporter gene. These assays were used to assess the estrogen and dioxin-like activities of naringenin, atrazine, and simazine and complex mixtures such as pulp and paper mill black liquor and urban air particulates. The activities of these chemicals and complex mixtures are confirmed using the pure antiestrogen ICI 164,384 and in in vitro gel retardation assays. Results of this study demonstrate the utility of in vitro recombinant receptor-reporter gene assays in identifying and assessing the estrogenic and dioxin-like activities of chemicals and complex mixtures.

Air Pollutants↗
PubMed1997

[Simple immunoassays of pesticides based on the biotin-streptavidin system].

A simple method was developed for the preparation of a highly active streptavidin-peroxidase conjugate that enhances fourfold the sensitivity of bioassays. Using this conjugate, a quantitative assay of simazine and 2,4-dichlorophenoxyacetic acid (competitive ELISA) and a noninstrumental express method for simultaneous detection of these pesticides (dot-immunofiltration assay) were developed. The detection limit of the pesticides is 3-4 and 2 ng/ml and the duration of the assays is 1.5 h and 5 min for ELISA and dot-immunofiltration, respectively. The express method is easy and straightforward and enables the assay to be performed outside the laboratory.

2,4-Dichlorophenoxyacetic Acid↗
PubMed2002

A biosensor for the detection of triazine and phenylurea herbicides designed using Photosystem II coupled to a screen-printed electrode.

A biosensor for the detection of triazine- and phenylurea-type herbicides was constructed using isolated Photosystem II (PS II) complexes as a biosensing element. PSII isolated from the thermophilic cyanobacterium Synechococcus elongatus was immobilized on the surface of a screen-printed sensor composed of a graphite working electrode and Ag/AgCl reference electrode deposited on a polymeric substrate. The biosensor was mounted in a flow microcell with illumination. The principle of the detection was based on the fact that herbicides selectively block PSII electron transport activity in a concentration-dependent manner. Changes of the activity were registered amperometrically as the rate of photoreduction of an artificial electron acceptor. The setup resulted in a reusable herbicide biosensor with a good stability (half-life of 24 h) and limit of detection of approximately 10(-9) M for diuron, atrazine and simazine.

Biosensing Techniques↗
PubMed2006

Determination of pesticides in washing waters of olive processing by gas chromatography-tandem mass spectrometry.

A simple and rapid SPE-GC method for the determination of 30 organochlorine, organophosphorus, and organonitrogen pesticides at ng/L levels in washing water of olive processing has been developed. Twenty-nine samples of water were collected directly in the inlet and outlet of the washing machines of three olive mills at various locations in Spain. Preconcentration and clean-up were performed by elution of the pesticides from a C18 SPE cartridge using dichloromethane. The target compounds were determined in the final extract by GC-MS/MS. The most frequently encountered pesticide residues were terbuthylazine, simazine, and diuron. In some of the water samples, coming from the inlet of the washing machines, terbuthylazine and diuron concentrations were above the maximum residue limit.

Food Handling↗
PubMed2006

psbA mutation (Asn266 to Thr) in Senecio vulgaris L. confers resistance to several PS II-inhibiting herbicides.

DNA sequence analysis of the psbA gene encoding the D1 protein of photosystem II (PS II), the target site of PS II-inhibiting herbicides, identified a point mutation (Asn266 to Thr) in a bromoxynil-resistant Senecio vulgaris L. population collected from peppermint fields in Oregon. Although this mutation has been previously reported in Synechocystis, this is the first report of this particular point mutation in a higher plant exhibiting resistance to PS II-inhibiting herbicides. The resistant population displayed high-level resistance to bromoxynil and terbacil (R/S ratio 10.1 and 9.3, respectively) and low-level resistance to metribuzin and hexazinone (R/S ratio 4.2 and 2.6, respectively) when compared with the susceptible population. However, the population was not resistant to the triazine herbicides atrazine and simazine or to the urea herbicide diuron. A chlorophyll fluorescence assay confirmed the resistance levels and patterns of cross-resistance of the whole-plant studies. The resistant S. vulgaris plants produced fewer seeds. Differences in cross-resistance patterns to PS II-inhibiting herbicides and the difference in fitness cost could be exploited in a weed management program.

DNA Mutational Analysis↗
PubMed2002

Computational chemistry study of the environmentally important acid-catalyzed hydrolysis of atrazine and related 2-chloro-s-triazines.

Many chlorine-containing pesticides, for example 2-chloro-s-triazines, are of great concern both environmentally and toxicologically. As a result, ascertaining or predicting the fate and transport of these compounds in soils and water is of current interest. Transformation pathways for 2-chloro-s-triazines in the environment include dealkylation, dechlorination (hydrolysis), and ring cleavage. This study explored the feasibility of using computational chemistry, specifically the hybrid density functional theory method, B3LYP, to predict hydrolysis trends of atrazine (2-chloro-N4-ethyl-N6-isopropyl-1,3,5-triazine-2,4-diamine) and related 2-chloro-s-triazines to the corresponding 2-hydroxy-s-triazines. Gas-phase energetics are described on the basis of calculations performed at the B3LYP/6-311++G(d,p)//B3LYP/6-31G* level of theory. Calculated free energies of hydrolysis (delta h G298) are nearly the same for simazine (2-chloro-N4,N6-diethyl-1,3,5-triazine-2,4-diamine), atrazine, and propazine (2-chloro-N4,N6-di-isopropyl-1,3,5-triazine-2,4-diamine), suggesting that hydrolysis is not significantly affected by the side-chain amine-nitrogen alkyl substituents. High-energy barriers also suggest that the reactions are not likely to be observed in the gas phase. Aqueous solvation effects were examined by means of self-consistent reaction field methods (SCRF). Molecular structures were optimized at the B3LYP/6-31G* level using the Onsager model, and solvation energies were calculated at the B3LYP/6-311++G(d,p) level using the isodensity surface polarizable continuum model (IPCM). Although the extent of solvent stabilization was greater for cationic species than neutral ones, the full extent of solvation is underestimated, especially for the transition state structures. As a consequence, the calculated hydrolysis barrier for protonated atrazine is exaggerated compared with the experimentally determined one. Overall, the hydrolysis reactions follow a concerted nucleophilic aromatic substitution (SNAr) pathway.

Acids↗
PubMed2002

Activity of mesotrione on resistant weeds in maize.

Mesotrione is a new callistemone herbicide that inhibits the HPPD enzyme (p-hydroxyphenylpyruvate dioxygenase) and introduces a new naturally selective tool into weed-management programmes for use in maize. Mesotrione provides control of the major broad-leaved weeds, and it can be used in integrated weed-management programmes depending on the grower's preferred weed-control strategy. At post-emergence rates of 150 g AI ha-1 or less, mesotrione provides naturally selective control of key species that may show triazine resistance (TR), e.g. Chenopodium album L, Amaranthus species, Solanum nigrum L, as well as species of weed that show resistance to acetolactase synthase (ALS) inhibitors e.g. Xanthium strumarium L, Amaranthus spp and Sonchus spp. The data presented show that resistant and susceptible biotypes of these species with resistance to triazine herbicides, such as atrazine, simazine, terbutylazine and metribuzin, or ALS-inhibitor herbicides, such as imazethepyr, remain susceptible to mesotrione. These results confirm that there is no cross-resistance in biotypes with target site resistance to triazine or ALS-inhibiting herbicides. It is important that herbicide choice and rotation becomes an integral part of planning weed management, so as to minimise the risks of crop losses from weed competition, build-up of weed seed in the soil and the further development of weed resistance across a range of herbicide modes of action.

Agriculture↗
PubMed2007

An electrospray membrane probe for the analysis of volatile and semi-volatile organic compounds in water.

A new membrane probe incorporating electrospray ionization (ESI) was designed, built and coupled to an ion trap mass spectrometer to detect low levels of semi-volatile organic compounds (SVOCs) in water. Similar to other membrane introduction mass spectrometry (MIMS) systems, the probe contains a capillary polydimethylsiloxane (PDMS) membrane to allow for the preferential permeation of small molecules but, in contrast, the interface uses a liquid/membrane/liquid interface rather than liquid/membrane/gas. The ESI source allows the probe to be operated at atmospheric pressure in positive or negative ionization mode and the lack of fragmentation in ESI allows for the simultaneous screening of many analytes with high sensitivity. The interface allows for the addition of additives to both the external and the internal liquid mobile phases to selectively improve permeation and/or the ionization efficiency of various classes of compounds. Characterization of the probe with methanol as the internal mobile phase showed that the signal for aniline optimized at 60 degrees C and an internal flow rate between 2-5 microL/min. The transfer of analyte through the membrane from water to methanol ensures a strong signal and robust electrospray for both positive and negative ion mode which is not typical when spraying pure water. Detection limits for aniline, pyridine and pentachlorophenol, and for the herbicides alachlor, atrazine, butachlor, metolachlor and simazine, were in the ppb to pptr range.

Environmental Monitoring↗
PubMed2000

High affinity ScFvs from a single rabbit immunized with multiple haptens.

We report the generation of single-chain Fv (scFv) fragments with high affinities against four different hapten molecules from a single immunised rabbit. The rabbit was immunised with a mixture of protein conjugates of four different haptens, namely the herbicide mecoprop and derivatives of the herbicides atrazine, simazine, and isoproturon. An scFv phage display library was constructed, and several scFvs with high affinity against each hapten were isolated. For each hapten, a single binder was selected by k(off) ranking and used for affinity determination. The affinities were in sub-nanomolar range and the lowest K(d) value obtained was 6.75 x 10(-10) M. An unusual feature of one of the anti-isoproturon scFvs was its ability to retain binding activity at pH1.7. The utility and potential of using a single animal and immunisation with multiple antigens for the production of multiple, specific, high affinity scFvs by phage display is discussed.

Amino Acid Sequence↗
PubMed1999

Biodegradation of s-triazine compounds by a stable mixed bacterial community.

The potential for biodegradation of s-triazine pesticides was investigated in laboratory batch and sequence batch experiments using a stable mixed bacterial community enriched on atrazine. The experiments were performed aerobically in a mineral salt solution complemented with a mixture of s-triazines as sole carbon and energy sources. Comparisons were made between the efficiency of the inoculum for atrazine degradation in mineral salt solution and in wastewater. In batch cultivation, atrazine, simazine, hydroxyatrazine, and terbutylazine were degraded to concentrations below 0.1 mg/liter after 6 days; evidence of the mineralization was the detection of 14CO2 from [U-ring-14C] atrazine and the production of nitrate and chloride ions. The low degradation rate observed for cyanuric acid and desethylatrazine suggests that degradation proceeded via N-dealkylation and dechlorination. Nevertheless, degradation of ametryne and cyromazine presume the involvement of other degradation pathways. Evidence was given that presence of other additional carbon sources is not an obstacle to atrazine biodegradation, since better results were obtained using wastewater.

Alcaligenes↗
PubMed2000

Fiber optic biosensor using Chlorella vulgaris for determination of toxic compounds.

A new biosensor is constructed for the detection of some herbicides based on kinetic measurements of chlorophyll-a fluorescence in Chlorella vulgaris cells. The microalgae are immobilized on removable membranes placed in front of the tip of an optical fiber bundle inside a homemade microcell. C. vulgaris was easily cultivated in laboratory and very sensitive to herbicides that effect the photosynthesis process. The response of the algal biosensor is studied in terms of detection limits, reversibility, and long-term activity. The effects of temperature and pH are also reported. The biosensor can be used to measure the concentration of a toxic chemical in the form of a single drop or dissolved in a continuous flow. The detection of 0.1 microg small middle dotL(-1) of a single herbicide as is required by European Community legislation for drinking water is possible with this algal biosensor especially for atrazine, simazine, and diuron.

Biosensing Techniques↗