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PubMed2005

A psbA mutation in Kochia scoparia (L) Schrad from railroad rights-of-way with resistance to diuron, tebuthiuron and metribuzin.

Kochia [Kochia scoparia (L) Schrad] has become resistant to many herbicides used in cropland and railroad rights-of-way in North Dakota and Minnesota. Kochia scoparia plants that had survived annual treatments with diuron and tebuthiuron were sampled along railroad rights-of-way in North Dakota and Minnesota. The samples were screened in the greenhouse for resistance to diuron, tebuthiuron, metribuzin and bromoxynil from 0.5x to 32x the recommended use rates. A resistant K scoparia accession (MN-3R) was confirmed with resistance up to 16-fold higher than recommended use rates for tebuthiuron and diuron and up to 4-fold higher for metribuzin. However, the resistant K scoparia accession was susceptible to bromoxynil even at 50% of the recommended use rate. The herbicide binding region of the psbA gene fragment of eight resistant (R) and seven susceptible (S) K scoparia accessions was PCR-amplified and sequenced for detection of mutations. The psbA gene of four R K scoparia accessions was mutated at residue 219 with substitution of isoleucine for valine (GenBank accession number AY251265). The seven S K scoparia accession sequences were wild-type at this residue (GenBank accession number AY251266). The other four R accessions sequences showed a previously known triazine R mutation with substitution of glycine for serine at residue 264. All 15 K scoparia accessions were wild-type at all other psbA residues within the region analyzed. Resistance to diuron, tebuthiuron and metribuzin among the railroad rights-of-way K scoparia is probably due to the mutation at residue 219 of the psbA gene in some plants, but due to the previously reported Ser(264)Gly substitution in other plants. Target-site resistance associated with a change of valine to isoleucine at residue 219 of the psbA target-site in weeds has previously been reported for Poa annua L selected in diuron-treated grass seed fields, and for Amaranthus powelli S Wats selected in linuron-treated carrot fields. This is the first report of the mutation in herbicide-resistant K scoparia.

Animals↗

PubMed2001

Evaluation of uncalibrated preferential flow models against data for isoproturon movement to drains through a heavy clay soil.

The uncalibrated predictive ability of four preferential flow models (CRACK-NP, MACRO/MACRO_DB, PLM, SWAT) has been evaluated against point rates of drainflow and associated concentrations of isoproturon from a highly structured and heterogeneous clay soil in the south of England. Data were available for four plots for a number of storm events in each of three successive growing seasons. The mechanistic models CRACK-NP and MACRO generally gave reasonable estimates of drainflow over the three seasons, but under-estimated concentrations of isoproturon over a prolonged period in the first season and over-estimated them in the two remaining seasons. CRACK-NP simulated maximum concentrations of isoproturon over the first two events of each of the three seasons of 156, 527 and 24.4 micrograms litre-1, respectively, and matched the observed data (465, 65.1 and 0.65 micrograms litre-1) slightly better than MACRO (69.1, 566 and 58.5 micrograms litre-1). Automatic selection of parameters from soils information within MACRO_DB reduced the emphasis on preferential flow relative to the stand-alone version of MACRO. This gave a poor simulation of isoproturon breakthrough and simulated maximum concentrations were 0, 50.1 and 35.1 micrograms litre-1, respectively. The capacity model PLM gave the best overall simulation of total drainflow for the first two events in each season, but over-estimated concentrations of isoproturon (967, 808 and 51.3 micrograms litre-1). The simple model SWAT represented total drainflow reasonably well and gave the best simulation of maximum isoproturon concentrations (140, 80.2 and 8.2 micrograms litre-1). There was no clear advantage here in using the mechanistic models rather than the simpler models. None of the models tested was able to simulate consistently the data set, and uncalibrated modelling cannot be recommended for such artificially drained heavy clay soils.

Aluminum Silicates↗

PubMed2001

Resistance to ACCase-inhibiting herbicides and isoproturon in UK populations of Lolium multiflorum: mechanisms of resistance and implications for control.

Herbicide-resistant Lolium multiflorum (Italian rye-grass) was first reported in the UK in 1993 and had been confirmed on 25 farms by 1999. In this study, resistance to five herbicides belonging to the aryloxyphenoxypropionate, cyclohexanedione and phenyl-urea classes was determined in six populations of L multiflorum from the UK under glasshouse and simulated field conditions. Glasshouse conditions tended to exaggerate the degree of resistance, but experiments performed in both environments detected resistance in four populations of L multiflorum. Four populations (Essex A1, Lincs A1, Wilts B1, Yorks A2) were resistant to diclofop-methyl, fluazifop-P-butyl, tralkoxydim and partially resistant to isoproturon, but only the population from Yorkshire (Yorks A2) showed resistance to cycloxydim. Biochemical analyses of acetyl coenzyme A carboxylase (ACCase) activity, oxygen consumption by thylakoids, diclofop metabolism and glutathione S-transferase activity showed that, in three of the resistant populations, an enhanced rate of herbicide metabolism conferred resistance. This is the first report world-wide of an enhanced metabolism mechanism of diclofop resistance in L multiflorum. In the Yorks A2 population, an insensitive ACCase was detected (target-site resistance) which also conferred cross-resistance to all of the other ACCase inhibitors investigated.

Acetyl-CoA Carboxylase↗

PubMed2001

Phototransformation of metoxuron [3-(3-chloro-4-methoxyphenyl)-1,1-dimethylurea] in aqueous solution.

UV irradiation of metoxuron in aerated aqueous solution at 254 nm or between 300 and 450 nm led initially to an almost specific photohydrolysis of the C-Cl bond, resulting in the formation of 3-(3-hydroxy-4-methoxyphenyl)-1,1-dimethylurea (MX3) and hydrogen chloride. The quantum yield was determined to be 0.020 (+/- 0.005) in solutions irradiated at 254 nm. Five minor photoproducts were also identified, in particular the dihydroxydimethoxybiphenyl derivatives resulting from the phototransformation of MX3. Irradiation increased the toxicity of an aqueous solution of metoxuron to the marine bacterium Vibrio fischeri.

Herbicides↗

PubMed2002

Spatial variability in herbicide degradation in the subsurface environment of a groundwater protection zone.

The aim of this study was to investigate the spatial variability in degradation and mineralization of atrazine and isoproturon in subsurface samples taken from sandy loam soils overlying gravel terraces which form part of a groundwater protection zone. Percussion drilling was used to obtain samples from 11 boreholes (maximum depth 3 m). Unlabelled atrazine or isoproturon, and ring-14C-labelled atrazine or isoproturon were added to samples, incubated at 25 degrees C for up to 16 weeks, and analyzed for the residual herbicide or [14C]carbon dioxide. All samples showed the potential to degrade these herbicides, although the percentage degradation decreased by a factor of 2-3 from the surface soil to a depth of 3 m. This was associated with a decrease in organic matter content, but there was no change in the potential to mineralize acetate, indicating that specific changes in the catabolic ability of the microbial population occurred with depth. The capacity of samples to mineralize atrazine and isoproturon to carbon dioxide decreased markedly with depth, with no mineralization potential observed at a depth of 80 cm.

Acetates↗

PubMed2001

Influence of topsoil tilth and soil moisture status on losses of pesticide to drains from a heavy clay soil.

Twelve lysimeters with a surface area of 0.5 m2 and a length of 60 cm were taken over mole drains from a Denchworth heavy clay soil and divided into two groups with either a standard agricultural tilth or a finer topsoil tilth. The influence of topsoil tilth on leaching of the herbicide isoproturon and a bromide tracer was evaluated over a winter season. The effect of variations in soil moisture status in the immediate topsoil on leaching of isoproturon, chlorotoluron and linuron was investigated in the following winter season. Here, water inputs were controlled such that lysimeters received 50 mm at a maximum intensity of 2 mm h-1 over a 4-week period with herbicides applied on day 15. Three treatments received the water either all prior to application, all after application, or evenly spread over the 4-week period. Leaching losses of the three herbicides were monitored for a subsequently drainage event. Analysis of covariance showed a significant effect of topsoil tilth and total flow on both the maximum concentrations (P = 0.034) and total losses (P = 0.012) of isoproturon in drainflow. Both concentrations and losses were c 35% smaller from lysimeters with the finer tilth. However, generation of the fine tilth in the field was restricted by a wet autumn and this is not considered a reliable management option for reducing pesticide losses from heavy clay soils. In the second experiment, variation in soil moisture content prior to and after application did not have any significant effect (P < 0.05) upon subsequent losses of the three herbicides to drains.

Aluminum Silicates↗

PubMed2002

New, quick tests for herbicide resistance in black-grass (Alopecurus myosuroides Huds) based on increased glutathione S-transferase activity and abundance.

Black-grass (Alopecurus myosuroides Huds) is a major grass weed in winter cereals in Europe. It reduces yields and can act as a secondary host for a range of diseases. Herbicide resistance in this species was first detected in the UK in the early 1980s, and has now been reported in thirty counties. To successfully manage herbicide resistance it is vital that suspect populations are tested so that appropriate action can be taken. Ideally, a test will be quick, cheap and easy to use. Furthermore, it should provide an unequivocal result before post-emergence herbicides are to be applied, allowing alternative strategies to be adopted where necessary. This paper reports the development of new tests for herbicide resistance based on our observation that the resistant black-grass biotype Peldon contains approximately double the activity of the enzyme glutathione S-transferase (GST) compared with susceptible biotypes. Data are presented on the production of a monoclonal antiserum to a novel 30 kDa GST polypeptide purified from the biotype Peldon. An ELISA using this antiserum is described and the utility of this assay to detect resistant black-grass biotypes in plants grown under glass and in the field is presented. In addition, a microtitre assay for GST activity is described, which allows the rapid assessment of GST activities of plants. Both abundance and activity of GSTs are discussed as markers for herbicide resistance in black-grass.

Drug Resistance↗

PubMed2002

Lysimeter study to investigate the effect of rainfall patterns on leaching of isoproturon.

The influence of five rainfall treatments on water and solute leaching through two contrasting soil types was investigated. Undisturbed lysimeters (diameter 0.25 m, length 0.5 m) from a sandy loam (Wick series) and a moderately structured clay loam (Hodnet series) received autumn applications of the radio-labelled pesticide isoproturon and bromide tracer. Target rainfall plus irrigation from the end of November 1997 to May 1998 ranged from drier to wetter than average (235 to 414 mm); monthly rainfall was varied according to a pre-selected pattern or kept constant (triplicate lysimeters per regime). Leachate was collected at intervals and concentrations of the solutes were determined. Total flow (0.27-0.94 pore volumes) and losses of bromide (3-80% of applied) increased with increasing inputs of water and were larger from the Wick sandy loam than from the Hodnet clay loam soil. Matrix flow appeared to be the main mechanism for transport of isoproturon through the Wick soil whereas there was a greater influence of preferential flow for the Hodnet lysimeters. The total leached load of isoproturon from the Wick lysimeters was 0.02-0.26% of that applied. There was no clear variation in transport processes between the rainfall treatments investigated for this soil and there was an approximately linear relationship (r2 = 0.81) between leached load and total flow. Losses of isoproturon from the Hodnet soil were 0.03-0.39% of applied and there was evidence of enhanced preferential flow in the driest and wettest treatments. Leaching of isoproturon was best described by an exponential relationship between load and total flow (r2 = 0.62). A 45% increase in flow between the two wettest treatments gave a 100% increase in leaching of isoproturon from the Wick soil. For the Hodnet lysimeters, a 35% increase in flow between the same treatments increased herbicide loss by 325%.

Aluminum Silicates↗

PubMed2003

Variation of pesticide sorption isotherm in soil at the catchment scale.

The variation of the sorption isotherm of pesticides has seldom been explored at the catchment scale. Such a study was conducted at the scale of a 187-ha agricultural catchment for three herbicides: atrazine, isoproturon and metamitron. Partition coefficient (Kd) values were measured in batch experiments on 51 topsoil samples, and showed moderate variability at the catchment scale (coefficient of variation CV approximately 30%). Values of Kd ranged from 0.47 to 1.70 litre kg(-1) for atrazine, 0.47 to 1.81 for isoproturon, and 0.55 to 2.21 for metamitron. A clustering method was used to reduce the number of samples on which to measure sorption isotherms to 14. Sorption isotherms agreed with the Freundlich rather than the linear model. Kf parameters had CV values similar to those for Kd, with values ranging from 0.78 to 2.13 mg(1 - Nf) litre(Nf) kg(-1) for atrazine, 0.61 to 1.82 for isoproturon, and 0.69 and 2.58 for metamitron. Nf exponents showed little variation (CV < 5%). Nf values were between 0.86 and 0.98 for atrazine, 0.85 and 0.90 for isoproturon, and 0.82 and 0.87 for metamitron. More than 97% of the Kf catchment-scale variations could be explained by the variations of the soil organic carbon content.

Agriculture↗

PubMed2003

Capacity of model biobeds to retain and degrade mecoprop and isoproturon.

Biobeds are used to increase the adsorption and degradation of pesticide spillage on sites used for mixing and loading and for cleaning of sprayers. The adsorption and the rate of degradation of 14C-labelled isoproturon and mecoprop (MCPP) at concentrations from 0.0005 to 25 000 mgkg(-1) were determined in biobed soil. Further leaching of the two herbicides was determined in a model biobed with a surface area of 2 m2. The biobed material showed enhanced ability to adsorb the two herbicides. Kd was 5.2 litre kg(-1) for isoproturon and 1.6 litre kg(-1) for MCPP in biobed material, which is higher than in natural soil. In different experiments with natural soil, Kd ranges from 0.07 to 0.6 litrekg(-1) for MCPP and from 1.5 to 4.6 litre kg(-1) for isoproturon in soils with varying organic carbon content. Degradation of MCPP was rapid at concentrations from 0.0005 to 500 mg kg(-1), delayed at 5000 mg kg(-1), and very slow at 25 000 mg kg(-1). For isoproturon, the relative degradation was most rapid at the lowest concentration and decreasing with increasing concentrations. After 120 days, between 55% and 8% 14C was evolved as 14CO2 at concentrations between 0.0005 and 25 000 mg kg(-1). The rate of evolution of 14CO2 indicated that degradation rates at low concentrations were of first-order and at higher concentrations of zero-order. Leaching of MCPP and isoproturon was determined in a newly established model biobed during a 2-year period. About 13% of applied MCPP and 1.4% of applied isoproturon leached out during the winter following the first autumn application (worst-case scenario). Leaching was completely prevented when the biobed had a well-developed grass cover and was covered during the winter.

2-Methyl-4-chlorophenoxyacetic Acid↗

PubMed2003

The ability of indigenous micro-organisms to degrade isoproturon, atrazine and mecoprop within aerobic UK aquifer systems.

The potential for the herbicides isoproturon, atrazine and mecoprop to degrade in the major UK aquifers of chalk, sandstone and limestone was studied using laboratory microcosms spiked at 100 microg litre(-1). Significant mecoprop degradation was only observed in sandstone groundwater samples. Atrazine transformation, based on the formation of metabolites, did occur in most groundwater samples, but only at a rate of 1-3% per year. A potential to degrade isoproturon was observed in groundwater samples from each of the aquifer types, with the most rapid and consistent degradation occurring at the sandstone field site. Biodegradation was confirmed by the formation of monodesmethyl- and didesmethyl-isoproturon. Isoproturon degradation potential rates obtained from the groundwater microcosms could not be correlated with either dissolved organic carbon or numbers of bacteria in the groundwater. It was noted that the ability of the groundwater at a field site to degrade a pesticide was not related to performance of the soil above.

2-Methyl-4-chlorophenoxyacetic Acid↗

PubMed2004

Climate change and decreasing herbicide persistence.

A herbicide degradation model, using real weather data for the period 1980-2001, has been used to estimate the change in persistence of autumn-applied isoproturon over this period. The results suggest that soil residues fell to the minimum for weed control on average approximately 30 days earlier over the last 5 years of this period than in the first 5 years, equivalent to a reduction of approximately 25% in the duration of weed control. This decline in persistence is attributed to increasing soil temperature. The results are discussed in relation to recent observations and predictions on climate change. The relevance of the findings to other pesticides and future weed control is considered.

Climate↗

PubMed2004

Metallothionein induction in aquatic oligochaete tubifex tubifex exposed to herbicide isoproturon.

Metallothioneins (MTs) are low-molecular-weight proteins mainly involved in metal ion detoxification. Recently it has been demonstrated that MTs participate in several cellular functions such as regulation of growth and antioxidative defenses. Moreover, pesticides can induce their synthesis. The aim of the current work was to determine the effects of isoproturon, either pure or formulated as Matin (suspension containing an isoproturon concentration of 500 g. L(-1)), on the metallothionein and total protein contents of the aquatic worm Tubifex tubifex. MT levels in exposed worms increased significantly after 7 and 15 days of exposure to a concentration of the herbicide of 50 mg. L(-1). Isoproturon reduced the metal (Cu, Zn, and Cd) content of metallothioneins, and it also increased the total protein content of the worms. These results suggest that MT induction may not be considered a specific biomarker of metal exposure but that it can be used as a nonspecific biomarker of the effect of isoproturon effect in aquatic worms.

Animals↗

PubMed2000

Increased sensitivity of tryptic peptide detection by MALDI-TOF mass spectrometry is achieved by conversion of lysine to homoarginine.

Mass spectrometric techniques for identification of proteins by "mass fingerprinting" (matching the masses of tryptic peptides from a protein digest to the theoretical peptides in a database) such as matrix-assisted laser desorption ionization-time of flight (MALDI-TOF) are rapidly growing in popularity as the demand for high throughput analysis of the proteome increases. This is due, in part, to the ability to automate the technique and the rapid rate with which mass spectra may be acquired. An important factor in the accuracy of the technique is the number of tryptic peptides that are identified in the various searching algorithms that exist. The greater sequence coverage of the parent protein that is obtained, the higher the level of confidence in the identification that is determined. One impediment to high levels of sequence coverage is the bias of MALDI-TOF mass spectrometry to arginine-containing peptides. Increasing the sensitivity to lysine-containing peptides should increase the sequence coverage obtained. In order to achieve this result we have developed conditions to modify the epsilon-amine group of lysine in tryptic peptides with O-methylisourea. The conditions utilized result in the conversion of lysine to homoarginine with no modification of the amine terminus of the peptides. The sensitivity of MALDI-TOF mass spectrometry detection of peptides was increased dramatically following modification. The modification chemistry may be applied to tryptic peptide mixtures prior to desalting and spotting onto MALDI-TOF plates. This technique will be particularly useful for identifying proteins with a high lysine/arginine ratio.

Amino Acid Sequence↗

PubMed1995

Herbicide isoproturon-specific binding in the freshwater macrophyte Elodea densa--a single-cell fluorescence study.

The experimental approach to the effects of the phenylurea herbicide Isoproturon (IPU), on the photosynthesis activity of leaf cells of the freshwater macrophyte Elodea densa was based on the fast induction kinetics of the PSII chlorophyll a in vivo fluorescence. FI/FP ratios determined on the induction curves exhibited a noticeable effect at 5 micrograms IPU.liter-1. They appeared to be the most reliable parameter for the quantitative evaluation of the dissociation constant of the complex "IPU/D1 protein" (Kd = 1.2 x 10(-7) M) and of the concentration of free IPU either at the thylakoid level or in the surrounding medium of the leaf epithelial cells. Total IPU bioaccumulation at the whole plant level as a function of [IPU] in the medium indicated that the D1 protein represented the main binding site for IPU in this aquatic plant species.

Binding Sites↗

PubMed1996

Availability and persistence of isoproturon under field and laboratory conditions.

Field and laboratory tests were conducted to investigate the disappearance and decrease in availability of the herbicide isoproturon in soil with time. Monitoring the fate of 14C-labeled isoproturon gave the persistence of the herbicide under different conditions. The calculated half-life (DT50) of the extractable parent product was close to 19 days for the two experiments, whereas half-lives of exhaustive extractable 14C-residues averaged 22 days under controlled conditions versus 48 days in the field. Moreover, if nonextractable 14C-residues were taken into account in estimating isoproturon fate, the DT50 of radioactive residues in soil (extractable parent and degradation products + nonextractable residues) reached 1 to 1.4 years under field and controlled conditions, respectively. The variability of disappearance rates for the different kinds of residues is discussed within a wider definition of persistence.

Biodegradation, Environmental↗

PubMed1997

Role of temperature on isoproturon bioaccumulation and effects on two freshwater rooted macrophytes: Elodea densa and Ludwigia natans.

The effects of temperature on the bioaccumulation of the phenylurea herbicide isoproturon (IPU) and on the growth inhibition induced on two freshwater rooted macrophytes--Elodea densa and Ludwigia natans--were investigated using indoor microcosms. The experimental protocol was based on five temperatures (12, 16, 20, 24, and 28 degrees C) and two contamination levels of the water column (30 and 60 micrograms IPU.liter-1), plus a control condition. Variations in temperature had little effect on the decrease in [IPU] in the water column during the 21-day experiment. The IPU concentration in the two macrophyte species was not significantly modified by the large range of temperatures when results were expressed using the concentration criterion. IPU burdens in the E. densa cuttings, on the other hand, increased significantly when the temperature rose from 12 to 28 degrees C; small differences were observed between the two exposure conditions, in relation to the antagonistic effects of IPU and temperature on the growth of the cuttings. Bioconcentration factors in the plants (stems + leaves) were close to 10 and 13 after exposure to 30 and 60 micrograms IPU.liter-1, respectively.

Anaerobiosis↗

PubMed2002

Uptake, metabolism, and effects on detoxication enzymes of isoproturon in spawn and tadpoles of amphibians.

Using ring-(14)C-labeled isoproturon (1 microg/L), the uptake into spawn and tadpoles of Bombina bombina and Bombina variegata was investigated. Two percent of the applied radioactivity was found per gram fresh weight in the embryo after 24h. Results indicate that the jelly mass of the spawn does not act as a sufficient physical barrier for protection against the uptake and influence of isoproturon (IPU) on the embryo. In vivo metabolism of ring-14C-labeled IPU by the cytochrome P-450 system was analyzed in tadpoles. Different metabolites of IPU, such as N-demethylated and C-hydroxylated derivatives, and the olefinic metabolite were detected. In tadpoles of B. variegata, the activity of microsomal and soluble glutathione-S-transferase (sGSTs) toward different model substrates was measured after treatment with IPU. Activities of sGST increased corresponding to elevated stress by IPU dependent on exposure time and dose. Compared to the pure active ingredient IPU, the commercial phenyl-urea herbicide Tolkan Flo, consisting of IPU and an emulsifier, also caused significantly elevated enzymatic response.

Animals↗