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PubMed2006

An in vitro screening assay to discover novel inhibitors of 4-coumarate:CoA ligase.

4-Coumarate:CoA ligase (4CL, EC 6.2.1.12) exists only in plants and plays an important role in the phenylpropanoid pathway. Identification of inhibitors targeting 4CL provides a novel approach for developing effective plant growth inhibitors (PGIs). The full-length gene of tobacco 4CL (Nt4CL1) was cloned and expressed in Escherichia coli Cast & Chalm. The recombinant 4CL protein was extracted and purified by several purification steps including gel-filtration and anion-exchange chromatography. 4CL activity assay was miniaturized and optimized using a 96-well microplate and a reader. Among 28 existing herbicides, propanil and swep strongly inhibited in vitro 4CL enzyme activity, and they were selected for further studies. The process of this assay can be developed into a high-throughput screening system of PGI targeting 4CL in the phenylpropanoid pathway.

Amino Acid Sequence↗
PubMed2006

The role of altered acetyl-CoA carboxylase in conferring resistance to fenoxaprop-P-ethyl in Chinese sprangletop (Leptochloa chinensis (L.) Nees).

From paddy field observations in 2002 and 2004, fenoxaprop-P-ethyl resistance in Chinese sprangletop (Leptochloa chinensis (L.) Nees) has been studied using information collected from 11 sites in the Saphan-Sung district of Bangkok, Thailand. The resistant Chinese sprangletop was found in nine rice fields, whereas the susceptible Chinese sprangletop was found in only two rice fields. In greenhouse experiments, both fenoxaprop-P-ethyl-resistant and susceptible Chinese sprangletop from the same location were investigated for 50% growth reduction based on phytotoxicity, plant height and fresh and dry weight. The resistant Chinese sprangletop showed apparent resistance at 14-21 days after herbicide application at a rate of 21.1-337.6 g AI ha(-1). The resistance index of resistant Chinese sprangletop was 10-25 times higher than that of the susceptible Chinese sprangletop. In addition, Chinese sprangletop did not exhibit multiple resistance to oxadiazon, propanil and quinclorac. According to acetyl-CoA carboxylase (ACCase) assays, the level of ACCase specific activity in the resistant Chinese sprangletop was significantly higher than that in the susceptible Chinese sprangletop. Similarly, the ACCase activity of the resistant Chinese sprangletop was 10 times less sensitive to fenoxaprop-P-ethyl than that of the susceptible Chinese sprangletop, based on the I50 values. The present study of the mechanism responsible for resistance in the biotypes investigated indicated that there was a close association between the concentration-response at the whole-plant level and ACCase sensitivity to fenoxaprop-P-ethyl, and resistance to fenoxaprop-P-ethyl was conferred by a modified ACCase at the target site, as suggested by higher specific activity and less sensitivity to the herbicide.

Acetyl-CoA Carboxylase↗
PubMed1977

Acute toxicities of selected herbicides to fingerling channel catfish, Ictalurus punctatus.

A scan of the acute toxicities of eighteen common herbicides to one-year-old channel catfish (Ictalurus punctatus) was conducted. Herbicides causing less than 10% mortality in 48 hr at 10 ppm were: alanap, chloramben, 2,4-D acid, 2,4-D dimethyl amine salt, dalapon, diuron, DSMA, EPTC, fluometuron, metribuzin, monuron, MSMA, nitralin and 2,4,5,-T. The 96-hr LC50 values in pp6 for four nerbicides found toxic were: propanil, 3796; trifluralin, 417; bensulide, 379; and DNBP 118. The toxicity of Dyanap, a mixture of DNBP and alanap, was lower than that of DNBP; there was no apparent synergism between DNBP and alanap in the mixture.

Animals↗
PubMed2005

Fully automated multianalyte determination of different classes of pesticides, at picogram per litre levels in water, by on-line solid-phase extraction-liquid chromatography-electrospray-tandem mass spectrometry.

This paper reports the development of a fully automated method for the multianalyte determination of twenty pesticides belonging to different classes (triazines, phenylureas, organophosphates, anilines, acidic, propanil, and molinate) in natural and treated waters. The method, based on on-line solid-phase extraction-liquid chromatography-electrospray-tandem mass spectrometry, is highly sensitive (limits of detection between 0.004 and 2.8 ng L(-1)), precise (relative standard deviations between 2.0 and 12.1%), reliable (two selected reaction-monitoring transitions are monitored per compound), rapid (45 min per sample), and simple. The application of this method to the monitoring of the target compounds in a waterworks revealed the presence of the pesticides investigated at concentrations up to 516 and 82 ng L(-1) (total pesticide concentration) in river water and ground water, respectively, used as sources, and their gradual removal through the purification process.

Automation↗
PubMed1994

Effects of two herbicidal wastewaters on Chlorella sp. and Phaeodactylum tricornutum.

The effects on Chlorella sp. and Phaeodactylum tricornutum of two industrial wastewaters known to contain the herbicide residues of Trifluralin and Propanil have been determined by monitoring the number of cells, the chlorophyll fluorescence and the carbon dioxide assimilation simultaneously for a period of 14 days. The growth of the diatom, Phaeodactylum tricornutum, was inhibited by concentrations of herbicidal waste of the order of 0.1-0.5%, apparently because the rate of reproduction was reduced. Chlorella sp. cells, on the other hand, whilst dramatically inhibited by 1% concentrations of herbicidal waste, were able to recover over a period of 14 days. If discharged at concentrations below 0.01%, the industrial wastes appeared not to affect phytoplankton.

Journal Article↗
PubMed1988

The impairment of mobility and development in freshwater snails (Physa fontinalis and Lymnaea stagnalis) caused by herbicides.

1. The pulmonate freshwater snails Physa and Lymnaea and the earthworms Eisenia and Lumbricus can take up and concentrate a carbamate herbicide (chlorpropham). 2. The mobility of freshwater snails was diminished in the presence of the herbicides chlorpropham (carbamate), cycloate (thiocarbamate), pentanochlor (amide) and chloroxurone (urea derivate). 3. The egg-assemblies of Lymnaea stagnalis turned out to be suitable objects for testing the influences of herbicides upon embryonic development. 4. In the presence of chlorpropham, chloroxurone, cycloate, propanil, simazine and terbutryne, all applied in concentrations lower than in practical use, the period of egg-maturing was delayed and the total number of dead embryos increased. 5. Developing snail eggs were very sensitive towards triazine herbicides (simazine, terbutryne) reflecting in an ED50-value lower than 10(-7) M. 6. Similar herbicidal-induced effects suggested that the developing stages of snail embryos may be suitable models for the ecologically more important but experimentally less accessible earthworms.

Animals↗
PubMed2004

Liquid chromatography-electrospray quadrupole ion-trap mass spectrometry of nine pesticides in fruits.

A liquid chromatographic method, with electrospray ionization tandem mass spectrometry (LC-ESI-MS-MS), has been developed for determining acrinathrin, carbosulfan, cyproconazole, lambda-cyhalothrin, kresoxim methyl, pyrifenox, pyriproxyfen, propanil, and tebufenpyrad in fruits. The ions prominent in ESI spectra were [M + H]+ and [M + Na]+. In the mass analyzer, collision-induced dissociation fragmentation involved common pathways, for example, product ions of [M + H]+ resulted from the cleavage of the carbamic group or an oxygen bound. The utility of the method is demonstrated by the analysis of crude extracts obtained by matrix solid-phase dispersion (MSPD) using C18 as dispersant and dichloromethane-methanol as eluent, and by solid-liquid extraction (SLE) with ethyl acetate and anhydrous sodium sulfate. Mean recoveries ranged from 51.5 to 108%, with relative standard deviations <16%, were obtained for MSPD and from 59 to 101% with relative standard deviation <17% for SLE. However, for most compounds, limits of quantification are better by SLE (0.01-4.4 mg kg(-1)) than by MSPD (0.05-2 mg kg(-1)). During the validation process, the procedure was tested for matrix effects, blanks and stability of the system. Considerably matrix effects in the ESI ionization process were detected by comparing standard calibration, and matrix calibration. Because of this, detected residues were quantified from interpolation against calibration data obtained using matrix matched standards.

Calibration↗
PubMed2005

Aquatic risk assessment of the new rice herbicide profoxydim.

A tiered protocol for assessing ecological risks has been applied to the rice pesticide profoxydim. The initial assessment (Tier I) was based on toxicity exposure ratio (TER) calculations based on laboratory data using a worst-case rice scenario. The first refinement (Tier II) was based on direct toxicity assessment (DTA) of water samples collected during a field-mesocosm study. Finally, a higher-tier assessment on the in situ assessment of paddy community responses (field-mesocosm-Tier III) was performed. A successive application of three pesticides, the herbicides azimsulfuron, propanil and the insecticide malathion, was used as reference controls. The refined assessments indicated a lower risk than that predicted from TER estimations. DTA-based Tier II showed toxicity effects only for concentrations above the recommended dose of profoxydim. Effects for reference controls were observed in DTA which were not expected from Tier I. The field-mesocosm study confirmed these effects but also showed that they were transient and of low relevance.

Agriculture↗
PubMed2004

The potential of pesticides to contaminate the groundwater resources of the Axios river basin in Macedonia, Northern Greece. Part I. Monitoring study in the north part of the basin.

The Axios river basin is an area of high agricultural importance for Macedonia, Northern Greece. High priced crops such as cotton, corn, sugarbeets, vegetables and rice are rotated with cereals and alfalfa and thus a great variety of pesticides are used annually for the control of pests and diseases. Moreover, the groundwater resources of the specific area constitute the main source of potable water for the surrounding cities and villages. Therefore, a study was initiated to investigate the probable risks of groundwater contamination with pesticides. The leaching of pesticides from agricultural soils was monitored in the phreatic horizon as well as in soil water samples collected with suction lysimeters. In parallel studies, the presence of pesticides in the irrigation water and the water of Axios river was also monitored. Pesticides like carbofuran, atrazine, alachlor and prometryne, which were regularly applied in the northern part of the basin during 1992-1994 were detected at concentrations occasionally exceeding 1 microg/l in soil water from the deeper soil layers and in the phreatic horizon. Residues of pesticides others than the ones applied in the studied area like propanil, terbufos and paraoxon-methyl were also detected at the deeper soil layers and in the phreatic horizon. The latter pesticides were also detected at significant concentrations in the irrigation water which mainly consisted of riverine water. The lack of an independent soil draining system and the use of riverine water for irrigation purposes resulted in the redistribution of residual amounts of these pesticides in the phreatic horizon beneath the agricultural area.

Agriculture↗
PubMed2004

The potential of pesticides to contaminate the groundwater resources of the Axios river basin. Part II. Monitoring study in the south part of the basin.

A monitoring study was conducted during 1992-1994 in the south part of the Axios river basin, which constitutes one of the main rice-cultivated basins of Greece. The potential of pesticides to contaminate groundwater resources was assessed under realistic agricultural conditions using suction lysimeters. Pesticide residues were also measured in local drainage canals, the phreatic horizon and Axios river. Carbofuran, atrazine, alachlor, prometryne and propanil were regularly detected at concentrations exceeding 1 microg/l in the soil water of deeper soil layers and in the phreatic horizon of the fields. Residues of those pesticides were measured in the soil water and the phreatic horizon of all the studied fields even though they had only been applied in certain fields. This almost uniform distribution of pesticide residues across the whole of the studied area was attributed to rice cultivation. Soil water and its pesticidal content was horizontally transported from saturated soil conditions beneath rice paddies to adjacent corn or cotton-cultivated fields with lower soil moisture contents. The presence of high pesticide concentrations in the water of the Axios river, which was used for the irrigation of the studied area, had probably contributed to the generalized pesticide contamination of the soil water in the studied area. These results suggest that there is a high risk for groundwater contamination in the basin.

Agriculture↗
PubMed2000

Determination of rice herbicides, their transformation products and clofibric acid using on-line solid-phase extraction followed by liquid chromatography with diode array and atmospheric pressure chemical ionization mass spectrometric detection.

A simultaneous method for the trace determination of acidic, neutral herbicides and their transformation products in estuarine waters has been developed through an on-line solid-phase extraction method followed by liquid chromatography with diode array and mass spectrometric detection. An atmospheric pressure chemical ionization (APCI) interface was used in the negative ionization mode after optimization of the main APCI parameters. Limits of detection ranged from 0.1 to 0.02 ng/ml for 50 ml of acidified estuarine waters preconcentrated into polymeric precolumns and using time-scheduled selected ion monitoring mode. Two degradation products of the acidic herbicides (4-chloro-2-methylphenol and 2,4-dichlorophenol) did not show good signal response using APCI-MS at the concentration studied due to the higher fragmentor voltage needed for their determination. For molinate and the major degradation product of propanil, 3,4-dichloroaniline, positive ion mode was needed for APCI-MS detection. The proposed method was applied to the determination of herbicides in drainage waters from rice fields of the Delta del Ebro (Spain). During the 3-month monitoring of the herbicides, 8-hydroxybentazone and 4-chloro-2-methylphenoxyacetic acid were successively found in those samples.

Atmospheric Pressure↗
PubMed2000

Monitoring of priority pesticides and other organic pollutants in river water from portugal by gas chromatography-mass spectrometry and liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.

Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-atmospheric pressure chemical ionization mass spectrometry (LC-APCI-MS) were optimized and applied for the trace-level determination of 42 priority pesticides and 33 priority organic pollutants from European Union Directive EC 76/464. First, off-line solid-phase extraction of 200 ml of river water using an OASIS solid-phase extraction cartridge, followed by GC-MS was used. Next, selected samples that were positive to GC-MS were analyzed by LC-APCI-MS in order to detect further polar byproducts or to improve the determination of previously detected polar analytes. The transformation products of triazine pesticides like deethylatrazine (DEA) and deisopropylatrazine (DIA) and compounds such as diuron and several chlorophenols were positively identified by LC-APCI-MS. The present methodology has also been used for searching for new analytes not included in the EC 76/464 list, like Irgarol, DEA and DIA. In addition it was applied to target pollutants in 43 river water samples from Portugal during a pilot survey from April to July 1999. Atrazine followed by simazine and 2,4,6-trichlorophenol were the most ubiquitous compounds detected in this area. The levels detected of the different compounds were in the range of: 0.01-2.73 microg/l, 0.05-0.74 microg/l, 0.02-1.65 microg/l, 0.02-5.43 microg/l, 0.01-0.40 microg/l, 0.01-0.26 microg/l, 0.02-0.61 microg/l, 0.01-3.90 microg/l, 0.01-1.24 microg/l, 0.02-2.3 microg/l, 0.01-0.13 microg/l and 0.01-0.5 microg/l for atrazine, simazine, terbuthylazine, alachlor, metolachlor, Irgarol, propanil; tributhylphosphate, diuron, 2,4,6-trichlorophenol, deisopropylatrazine and deethylatrazine, respectively.

Atmospheric Pressure↗
PubMed1991

Simultaneous separation and determination of hydrocarbons and organochlorine compounds by using a two-step microcolumn.

The simultaneous separation and determination of a mixture of hydrocarbons and organochlorine compounds was successfully carried out by using sorption chromatography on a two-step microcolumn of silica and aluminium oxide for their fractionation, and a dual detector system. In addition to the separation and identification of hydrocarbons and heterocompounds containing nitrogen, oxygen and sulphur atoms, separation and identification of chlorinated hydrocarbons (dichlorobenzenes, p-chlorotoluene, hexachlorobutadiene, 1,2,4-trichlorobenzene and 2-chloronaphthalene), pesticides (chlorpicrin, aldrin, lindane, alpha- and beta-benzene hexachloride (BHC), endrin, dieldrin, endosulphan, methoxychlor) and herbicides (propanil, dichlobenil, trifluralin, difolatan) were achieved in mixtures containing polychlorinated biphenyl, strobane and chlordane.

Chromatography↗
PubMed1998

Monitoring of pesticide residues and their metabolites in surface and underground waters of Imathia (N. Greece) by means of solid-phase extraction disks and gas chromatography.

Seasonal variations of pesticide residues in surface waters and ground waters of the Imathia area of Central Mecedonia (N. Greece) were determined for the period from May 1996 to April 1997. The sampling cruises included eight sites in rivers Aliakmon, Loudias, Tripotamos, Arapitsa and Canal-66, seven water springs in the mountain Vermion, seven rainfall water collection stations and one hundred underground points. Solid-phase extraction disks followed by gas chromatographic techniques with flame thermionic detection, electron capture detection and mass-selective detection were used for the monitoring of various pesticides their transformation products in environmental waters. The most commonly encountered pesticides in underground waters, were alachlor, atrazine, desethylatrazine (DEA), metolachlor, molinate, propanil, simazine, carbofuran, diazinon and parathion methyl. The above compounds including propazine, trifluralin, malathion, parathion ethyl, lindane, alpha-benzene hexachloride (alpha-BHC), beta-BHC, 4,4'-DDE and heptachlor were determined in river waters. The higher concentrations in underground waters were measured during the period from May to August, 1996, following seasonal application and diminished significantly during the autumn and winter. Water pollution by triazine and chloroacetanilides was highest in the estuarine areas; showing that many of these compounds are transported significant distances from their application sites. The major inputs of atrazine, alachlor, simazine and metolachlor occurred in May and June just after their application. Atrazine, DEA, diazinon and metolachlor were also detected in spring waters at concentration levels below 0.006 microgram/l. Finally, atrazine, DEA, carbofuran, simazine, diazinon, parathion ethyl and parathion methyl were detected in rainfall water samples collected in the agricultural area of Imathia (central part of the plain).

Agriculture↗
PubMed2001

3,4-Dichlorophenylhydroxylamine cytotoxicity in renal cortical slices from Fischer 344 rats.

3,4-Dichlorophenylhydroxylamine (3,4-CPHA) is the N-hydroxyl metabolite of 3,4-dichloroaniline. 3,4-Dichloroaniline is a breakdown product of the herbicide Propanil. Previous work has shown that 3,4-dichloroaniline is acutely toxic to the kidney and bladder. The purpose of this study was to examine the in vitro toxicity of 3,4-dichlorophenylhydroxylamine. Renal cortical slices were prepared from male Fischer 344 rats (190-250 g) and were incubated with 0-0.5 mM 3,4-CPHA for 30-120 min under oxygen and constant shaking. 3,4-CPHA produced a concentration and time dependent alteration in lactate dehydrogenase (LDH) leakage, organic ion accumulation and pyruvate stimulated gluconeogenesis. Glutathione levels were diminished within 60 min below control values by 0.1 and 0.5 mM 3,4-CPHA. A 30 min pretreatment with 0.1 mM deferoxamine did not alter 3,4-CPHA toxicity. Alterations in pyruvate stimulated gluconeogenesis and LDH leakage were comparable between vehicle and deferoxamine pretreated tissues. Other studies examined the effect of (1 mM) glutathione, 2 mM ascorbic acid and 1 mM dithiothreitol (DTT) on toxicity. Pretreatment for 30 min with vehicle or 1 mM DTT induced comparable changes in LDH leakage and pyruvate stimulated gluconeogenesis. Pretreatment for 30 min with 1 mM glutathione or 2 mM ascorbic acid reduced 3,4-CPHA toxicity. LDH leakage was not elevated as markedly in renal slices pretreated with glutathione relative to slices pretreated with vehicle. These results indicate that 3,4-CPHA toxicity is through an iron independent mechanism. 3,4-CPHA cytotoxicity was reduced by pretreatment with glutathione or ascorbic acid suggesting formation of a reactive intermediate.

Analysis of Variance↗
PubMed1997

Baker's yeast biomass (Saccharomyces cerevisae) for selective on-line trace enrichment and liquid chromatography of polar pesticides in water.

Baker's yeast cells (Saccharomices cerevisae) were successfully immobilized onto silica gel and used in the on-line isolation and trace enrichment of desisopropylatrazine, desethylatrazine, hydroxyatrazine, simazine, cyanazine, atrazine, carbaryl, propanil, linuron, and fenamiphos. Since humic and fulvic acids were not coextracted, no cleanup was necessary. The pesticides were spiked at 0.1-1 microgram L-1 in tap water, groundwater, and seawater and were preconcentrated using on-line solid-phase extraction into a yeast immobilized on silica gel precolumn followed by liquid chromatography with diode array detection. All the variables that affect the enrichment step, such as amount of yeast immobilized, dimensions of the precolumn, sample pH, and preconcentration flow rate, were optimized. The degree of selectivity was evaluated by comparing the chromatograms obtained after on-line sample preconcentration on the yeast precolumn with those obtained by on-line solid-phase extraction using a precolumn filled with C18 material. The relative standard deviation for the whole procedure in the determination of the selected pesticides at the 0.3 microgram L-1 concentration level ranged from 1 to 9%, depending on the pesticide and the type of water. Detection limits within the range 0.01-0.5 microgram L-1 were obtained by percolating only 25 mL of water sample without any additional cleanup step.

Biomass↗
PubMed1999

Hydrolysis of naptalam and structurally related amides: inhibition by dissolved metal ions and metal (hydr)oxide surfaces.

In metal ion-free solutions, the secondary amide naptalam hydrolyzes more rapidly as the pH is decreased; intramolecular nucleophilic attack by a carboxylate side group is very likely involved. Millimolar levels of dissolved Cu(II) and Zn(II) inhibit hydrolysis between pH 3.6 and pH 6.5. Metal ion-naptalam complex formation is important since addition of the competitive ligand citrate lessens the inhibitory effect. The metal (hydr)oxide surfaces Al(2)O(3) and FeOOH inhibit naptalam hydrolysis to a lesser degree; inhibition is proportional to the extent of naptalam adsorbed. Secondary amides (propanil, salicylanilide, and N-1-naphthylacetamide) and tertiary amides (N-methyl-N-1-naphthylacetamide, furalaxyl, and N, N-diethylsalicylamide) that lack carboxylate side groups do not hydrolyze within 45 days of reaction, even when millimolar Cu(II) concentrations are present. Tertiary amides possessing carboxylate side groups (N,N-diethyl-3,6-difluorophthalamic acid and N, N-dimethylsuccinamic acid) do hydrolyze but are insensitive to the presence or absence of Cu(II). The inhibitory effect is believed to occur via metal coordination of (1) the carbonyl group of naptalam, which induces deprotonation of the amide group and makes the substrate less reactive toward nucleophilic attack; (2) the free carboxylate group of naptalam, which blocks intramolecular nucleophilic attack; or (3) a combination of the two.

Agrochemicals↗
PubMed1989

WHO drinking water quality guidelines for selected herbicides.

Following the successful introduction of its Guidelines for Drinking-Water Quality in 1984, the WHO Regional Office for Europe was approached by the Government of Italy to develop, as a matter of urgency, recommendations for guidelines levels of certain herbicides found in drinking water supplies. Realizing the extent of the problem, the Regional Office for Europe organized two consultations to develop drinking water quality guidelines for the following 11 herbicides most commonly used in Italy: alachlor, metolachlor, pyridate, atrazine, molinate, simazine, bentazon, pendimethalin, trifluralin, MCPA and propanil. The presence of these and other herbicides in ground and surface water has been reported in several countries. Although the main purpose of these guidelines is to provide guidance to the Government of Italy in making risk management decisions, the information given was also intended to assist the other countries of the European Region in setting standards or in developing alternative control procedures where the implementation of standards is not feasible. The purpose of this paper is to review the process of health risk assessment used in the development of the WHO drinking water quality guidelines for selected herbicides. It will also reveal the major dilemmas and concerns expressed by the participating experts during the process of scientific deliberations, in the interests of understanding the complex issues involved in reaching the bare figures of the recommended guidelines.

Herbicides↗