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PubMed1989

Tumour initiatory activity of a herbicide diuron on mouse skin.

In the present investigation, the tumour initiating activity of a herbicide diuron 3-(3,4 dichlorophenyl)-1,1 dimethyl urea has been observed following multiple topical applications at a dose of 250 mg/kg body weight in a standard two-stage initiation-promotion protocol on mouse skin for carcinogenicity testing. It was found that 9 applications of the herbicide given on the interscapular region in a thrice weekly schedule up to 3 weeks and followed, after 1 week, by the repeated 3 times per week application of a known skin tumour promoter 12-O-tetradecanoyl phorbol 13-acetate (TPA), 5 micrograms dissolved in 100 microliters of acetone in the same initiated area, led to the development of benign skin tumours. However, a single dose of diuron, used for each application as above and followed by repeated TPA applications, with the same dose and painting schedule as in the case of multiple applications, failed to initiate tumour development.

Animals↗
PubMed1995

Sequences of the cDNAs encoding the heavy- and light-chain Fab region of an antibody to the phenylurea herbicide diuron.

The cDNAs from a hybridoma (mAb 481.1) specific for diuron, a widely used phenylurea herbicide, were cloned into the phage display vector pComb8. Antigen-binding clones were selected by panning on diuron-hapten-BSA conjugates. The nucleotide and deduced amino-acid sequences encoding the Fab regions of the light (kappa) and heavy (gamma) chains were determined. The light chain was from mouse kappa chain subgroup III and the heavy chain was a member of the mouse H chain subgroup III(d).

Amino Acid Sequence↗
PubMed2006

On-line immunoaffinity column-liquid chromatography-tandem mass spectrometry method for trace analysis of diuron in wastewater treatment plant effluent sample.

An on-line immunoaffinity column with liquid chromatography/tandem mass spectrometry (IAC-LC-MS/MS) method for the determination of diuron in water matrices was described. This method used a sol-gel immunoaffinity column (20 mm x 4 mm I.D.) for on-line sample cleanup and enrichment, a monolithic analytical column (100 mm x 4.6 mm I.D.) for separation, and a triple quadrupole mass spectrometer for quantitation. The major challenges for the on-line set-up were discussed. The optimized on-line protocol was emphasized by the fact that low limit of quantitation (LOQ) of 1.0 ng/L was achieved with only 2.5-mL sample. In addition, a satisfactory accuracy ( approximately 90% of recovery) and precision (<6% of relative standard deviation) at 50 ng/L concentration were also obtained. Due to the ability of the sol-gel immunoaffinity column to eliminate matrix effect, the on-line IAC-LC-MS/MS analysis method can reliably determine diuron in wastewater treatment plant effluent sample.

Chromatography, Affinity↗
PubMed2006

Fate of Irgarol 1051, diuron and their main metabolites in two UK marine systems after restrictions in antifouling paints.

Two major antifouling biocides used worldwide, Irgarol 1051 and diuron, and their degradation products in Shoreham Harbour and Brighton Marina, UK were studied during 2003-2004. The highest concentrations of Irgarol 1051 were 136 and 102 ng L(-1) in water and 40 and 49 ng g(-1) dry weight in sediments for Shoreham Harbour and Brighton Marina, respectively. As the degradation product of Irgarol 1051, M1 was also widespread, with the highest concentration of 59 ng L(-1) in water and 23 ng g(-1) in sediments in Shoreham Harbour, and 37 ng L(-1) in water and 5.6 ng g(-1) in sediments in Brighton Marina. The target compounds showed enhanced concentrations during the boating season (May-July), when boats were being re-painted (January-February), and where the density of pleasure crafts was high. Overall, the concentration of Irgarol 1051 decreased significantly from late 2000 to early 2004, indicating the effectiveness of controlling its concentrations in the marine environment following restricted use. Diuron was only detected in 14% of water samples, and mostly absent from sediment samples.

Biotransformation↗
PubMed2005

Degradation and leaching of the herbicides metolachlor and diuron: a case study in an area of Northern Italy.

In this work the degradation of the herbicides metolachlor, diuron, monuron and of the metabolites 2-ethyl-6-methylaniline (EMA), and 3,4-dichloroaniline (DCA) was assessed in laboratory experiments on microbiologically active and sterilized soils. Their leaching potentials were calculated, using Gustafson's equation, by determining their mobility (as Koc) and persistence (expressed as DT50). Lysimeter experiments were also conducted to assess the actual leaching of the studied herbicides in a cereal crop tillage area vulnerable to groundwater contamination. The data obtained from the field were compared to the laboratory results. Moreover, some compounds of particular concern were searched for in the groundwater located near the experimental area in order to evaluate actual contamination and to test the reliability of the leaching potential. The GUS index, computed on data from microbiologically active soil, shows monuron as a leacher compound, EMA and DCA as non-leachers, metolachlor and diuron as transient ones. The presence of metolachlor in the groundwater monitored, even at concentrations up to 0.1 mug/l, confirms the possibility that transient compounds can be leached if microbial activity has not completely occurred in active surface soil.

Acetamides↗
PubMed2002

Biotransformation of phenylurea herbicides by a soil bacterial strain, Arthrobacter sp. N2: structure, ecotoxicity and fate of diuron metabolite with soil fungi.

In order to assess the influence of the aromatic substitution on the ability of a soil bacterial strain, Arthrobacter sp. N2, to degrade phenylurea herbicides, biotransformation assays were performed in mineral medium with resting cells of this soil bacterial strain on three phenylurea herbicides (diuron, chlorotoluron and isoproturon). Each herbicide considered, led to the formation of only one metabolite detected by HPLC analysis. After isolation, the metabolites were identified by NMR and MS, as the corresponding substituted anilines. According to the Microtox test (realized on the bacterium Vibrio fischeri), these metabolites presented non-target toxicity far more important (up to 600 times higher for 4-isopropylaniline) than the parent molecule. For isoproturon and chlorotoluron, the amount of substituted anilines obtained at the end of the biotransformation was very low, whereas the biotransformation of diuron into 3,4-dichloroaniline was almost quantitative. In this last case, the degradation product accumulated in the medium. In soil, other microorganisms are present that might degrade it. So the biotransformation of 3,4-dichloroaniline was then tested with four fungal strains: Aspergillus niger, Beauveria bassiana, Cunninghamella echinulata var. elegans and Mortierella isabellina. The aniline was further transformed with all the microorganisms tested. Only one metabolite was detected by HPLC analysis and after isolation, it was identified to be 3,4-dichloroacetanilide. This acetylated compound led to biological effects less important on V. fischeri than 3,4-dichloroaniline. These results stress the importance of identifying the degradation products to assess the impact of a polluting agent. Indeed, the pollutant may undergo transformation yielding compounds more toxic than the parent molecule.

Arthrobacter↗
PubMed2003

Photocatalytic treatment of diuron by solar photocatalysis: evaluation of main intermediates and toxicity.

The technical feasibility, mechanisms, and performance of degradation of aqueous diuron (22 mg/L) have been studied at pilot scale in two well-defined photocatalytic systems of special interest because natural UV light can be used: heterogeneous photocatalysis with titanium dioxide and homogeneous photocatalysis by photo-Fenton. Equivalent pilot-scale (made up of Compound Parabolic Collectors (CPCs) specially designed for solar photocatalytic applications) and field conditions used for both allowed adequate comparison of the degree of mineralization and toxicity achieved as well as the transformation products generated en route to mineralization by both systems. Total disappearance of diuron is attained by both phototreatments in 45 min. 100% of chlorine was recovered as chloride, but total recovery of nitrogen as inorganic ions was not attained. 90% of mineralization was reached after 200 min of photocatalytic treatment, but toxicity measured by two different bioassays (Daphnia magna and a Microalga) was reduced to below the threshold (EC50%) in a shorter time. Transformation products evaluated by LC-IT-MS by direct injection of the samples were the same in both cases. The main differences between the two processes were in the amount of transformation products (DPs) generated, not in the DPs detected, which were always the same.

Animals↗
PubMed2006

Sorption of carbofuran and diuron pesticides in 43 tropical soils of Sri Lanka.

To better understand the environmental fate of pesticides in Sri Lankan soils, we studied the sorption behavior of two commonly used pesticides (carbofuran and diuron) in 43 surface soils representing a range of soil physicochemical properties from dry and wet zones of Sri Lanka. For carbofuran, the K(d) (L/kg) values varied from 0.11 to 4.1 (mean, 0.83; median, 0.62) and K(oc) ranged from 7.3 to 120.6 (mean, 41.65; median, 36.1), whereas for diuron K(d) values varied from 0.5 to 75 (mean, 9.6; median, 5.15) and K(oc) ranged from 55.3 to 962 (mean, 407; median, 328). A comparison of sorption data on these tropical soils with published studies (mostly European and north American soils) showed that the ranges of sorption coefficients from Sri Lankan soils were within the wide range of K(oc) values reported in the literature. However, these values for both pesticides in soils from dry zones of Sri Lanka were consistently higher (up to two times) than those from the wet zone. The wide range of K(oc) values in Sri Lankan soils may be due to the possible difference in the nature of soil organic carbon, which needs to be further investigated.

Adsorption↗
PubMed2006

Sorption and desorption behaviors of diuron in soils amended with charcoal.

Charcoal derived from the partial combustion of vegetation is ubiquitous in soils and sediments and can potentially sequester organic contaminants. To examine the role of charcoal in the sorption and desorption behaviors of diuron pesticide in soil, synthetic charcoals were produced through carbonization of red gum (Eucalyptus spp.) wood chips at 450 and 850 degrees C (referred to as charcoals BC450 and BC850, respectively, in this paper). Pore size distribution analyses revealed that BC850 contained mainly micropores (pores approximately 0.49 nm mean width), whereas BC450 was essentially not a microporous material. Short-term equilibration (< 24 h) tests were conducted to measure sorption and desorption of diuron in a soil amended with various amounts of charcoals of both types. The sorption coefficients, isotherm nonlinearity, and apparent sorption-desorption hysteresis markedly increased with increasing content of charcoal in the soil, more prominently in the case of BC850, presumably due to the presence of micropores and its relatively higher specific surface area. The degree of apparent sorption-desorption hystersis (hysteresis index) showed a good correlation with the micropore volume of the charcoal-amended soils. This study indicates that the presence of small amounts of charcoal produced at high temperatures (e.g., interior of wood logs during a fire) in soil can have a marked effect on the release behavior of organic compounds. Mechanisms of this apparent hysteretic behavior need to be further investigated.

Adsorption↗
PubMed2004

Characterization of aqueous and solid inclusion complexes of diuron and isoproturon with beta-cyclodextrin.

The interaction of diuron and isoproturon herbicides with beta-cyclodextrin is conducive to the formation of inclusion compounds in aqueous solution as well as in the solid state. The physico-chemical study of these complexes was carried out by various analytical techniques such as ultraviolet (UV), Fourier transform infrared (FT-IR), Raman, X-ray diffraction, and 1H-NMR (nuclear magnetic resonance) spectroscopies. The existence of inclusion complexes in water solution between the beta-cyclodextrin and each of the herbicides was revealed by electronic absorption and 1H-NMR spectroscopies. A 1:1 stoichiometry was determined for both complexes in aqueous medium from UV absorption spectra by using the Benesi-Hildebrand method; the relative stability constants at room temperature were calculated at 2700 +/- 300 L mol(-1) and 750 +/- 50 L mol(-1) for isoproturon and diuron, respectively. In the solid state, inclusion processes with beta-cyclodextrin were characterized by means of infrared and Raman techniques and confirmed by X-ray diffraction spectra.

Cyclodextrins↗
PubMed1997

Effect of diuron on germ cells of mice.

Diuron in both, acute (340 and 170 mg/kg body wt) and chronic (3400 ppm) doses induced dominant lethal mutations in male Swiss albino mice. The results suggest that diuron is mutagenic in dominant lethal test system.

Animals↗
PubMed2002

Evaluation of the effects of diuron and its derivatives on Lemna gibba using a fluorescence toxicity index.

The herbicide diuron (DCMU) [3-(3,4-dichlorophenyl)-1,1-dimethylurea] is largely used in agricultural practices which contribute to water pollution in large areas. Its degradation induced by light or microbial activity is known to be a slow process, and may result in the accumulation of DCMU derivatives in the environment. In this report we used the yield of PSII variable fluorescence of Lemna gibba affected by the DCMU derivatives DCPMU [1-(3,4-dichlorophenyl)-3-methylurea], DCPU [1-(3,4-dichlorophenyl)urea], and DCA [3,4-dichloroaniline] to calculate the fluorescence toxicity index. We found the fluorescence toxicity index to be a useful parameter to evaluate the inhibitory effect on PSII electron transport in L. gibba exposed to DCMU and its derivatives. The variations observed for the inhibitory effect between DCMU and its derivatives seem to be caused by the modification of the dimethylurea group within the DCMU molecule. The fluorescence toxicity index demonstrated a strong quantitative dependency between the inhibitory effect of PSII electron transport and pollutant concentrations. We propose the fluorescence toxicity index to be a useful tool for future bioassays in evaluating the quality of water polluted with herbicides that induce an inhibition to PSII photochemistry.

Araceae↗
PubMed1979

Genetic localization of diuron- and mucidin-resistant mutants relative to a group of loci of the mitochondrial DNA controlling coenzyme QH2-cytochrome c reductase in Saccharomyces cerevisiae.

Diuron-resistance, DIU (Colson et al., 1977), antimycin-resistance, ANA (Michaelis, 1976; Burger et al., 1976), funiculosin-resistance, FUN (Pratje and Michaelis, 1977; Burger et al., 1977) and mucidin-resistance, MUC (Subik et al., 1977) are each coded by a pair of genetic loci on the mit DNA of S. cerevisiae. In the present paper, these respiratiory-competent, drug-resistant loci are localized relative to respiratory-deficient BOX mutants deficient in coenzyme QH2-cytochrome c reductase (Kotylak and Slonimski, 1976, 1977) using deletion and recombination mapping. Three drug-resistant loci possessing distinct mutated allelic forms are distinguished. DIU1 is allelic or closely linked to ANA2, FUN1 and BOX1; DIU2 is allelic or closely linked to ANA1, MUC1 and BOX4/5; MUC2 is allelic to BOX6. The high recombinant frequencies observed between the three loci (13% on the average for 33 various combinations analyzed) suggest the existence of either three genes coding for three distinct polypeptides or of a single gene coding for a single polypeptide but subdivided into three easily separable segments. The resistance of the respiratory-chain observed in vitro in the drug-resistant mutants and the allelism relationships between respiratory-competent, drug-resistant loci and coQH2-cyt c reductase deficient, BOX, loci strongly suggest that each of the three drug-resistant loci codes for a structural gene-product which is essential for the normal coQH2-cyt c reductase activity and is obviously a good candidate for a gene product of the drug-resistant loci mapped in this paper. Polypeptide length modifications of cytochrome b were observed in mutants deficient in the coQH2-cyt c red and localized at the BOX1, BOX4 and BOX6 genetic loci (Claisse et al., 1977, 1978) which are precisely the loci allelic to drug resistant mutants as shown in the present work. Taken together these two sets of data provide a strong evidence in favor of the idea that there exist three non contiguous segments of the mitochondrial DNA sequence which code for a single polypeptide sequence of cytochrome b. In each segment mutations which modify the polypeptide sequence can occur leading to the loss (BOX mutants) or to a modification (drug resistant mutants) of the enzyme activity.

Antifungal Agents↗
PubMed1977

Induction of hepatic microsomal enzymes by diuron, phenobenzuron, and metabolites in rats.

Microsomal liver enzymes are induced in rats which are fed a diet containing 1000 ppm of phenobenzuron, a phenylurea herbicide, for 7 days: All parameters measured are about 50% higher than control values. This increase is lower after 14 feeding days. Diuron and 3,4-dichloroaniline have a similar, although lower, effect than phenobenzuron. Two other metabolites have no action on microsomal enzymes. The transitory and weak inducing effect of these phenylureas is interesting when compared to other organochlorine pesticides.

Animals↗
PubMed1984

3,3',4,4'-Tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene in technical grade herbicides: propanil, diuron, linuron, and neburon.

The levels of 3,3',4,4'-tetrachloroazobenzene (TCAB) and 3,3',4,4'-tetrachloroazoxybenzene (TCAOB) were determined by gas chromatography-electron capture detection in 20 samples of 3,4-dichloroaniline-derived herbicides. The concentrations of TCAB in technical grade propanil, diuron, linuron, and neburon from a variety of manufacturers ranged from 0.10 to 28.40 mg/kg. No relevant difference was found between the two different herbicide classes analyzed.

Azo Compounds↗
PubMed1990

Dose-related induction of rat hepatic drug-metabolizing enzymes by diuron and chlorotoluron, two substituted phenylurea herbicides.

Dose-related induction of various hepatic drug-metabolizing enzymes has been investigated after short-term treatment of rats by diuron and chlorotoluron, a dichlorinated and a monochlorinated phenylurea herbicide, respectively. Results suggest that 'saturation' of the induction system of benzo(a)pyrene monooxygenase, 7-ethoxycoumarin O-deethylase and 7-ethoxyresorufin O-deethylase activities may occur in the same range of the molar doses of both compounds, and with the dichlorinated herbicide at much higher activities. Induction of epoxide hydrolase, UDP-glucuronyltransferase and glutathione S-transferases also shows saturation curves in the function of molar doses. However, the structural difference is not reflected in the enhancement of enzyme activities.

7-Alkoxycoumarin O-Dealkylase↗
PubMed2004

A new, versatile field immunosensor for environmental pollutants: development and proof of principle with TNT, diuron, and atrazine.

This paper presents a new, versatile, portable miniaturized flow-injection immunosensor which is designed for field analysis. The temperature-controlled field prototype can run for 6h without external power supply. The bio-recognition element is an analyte-specific antibody immobilized on a gold surface of pyramidal structures inside an exchangeable single-use chip, which hosts also the enzyme-tracer and the sample reservoirs. The competition between the enzyme-tracer and the analyte for the antigen-binding sites of the antibodies yields in the final step a chemiluminescence signal that is inversely proportional to the concentration of analyte in the given range of detection. A proof of principle is shown for nitroaromatics and pesticides. The detection limits (DL; IC20) reached with the field prototype in the laboratory was below 0.1 microg l(-1) for 2,4,6-trinitrotoluene (TNT), and about 0.2 microg l(-1) for diuron and atrazine, respectively. Important aspects in this development were the design of the competition between analyte and enzyme-tracer, the unspecific signal due to unspecific binding and/or luminescence background signal, and the flow pattern inside the chip.

Atrazine↗