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PubMed2001

Pesticide poisoning initially suspected as a natural death.

A pesticide poisoning victim suspected initially as having died a natural death was autopsied. The victim was a 47-year-old male. Macroscopically, signs of acute death and, in particular, general erosion in the mucosa of the airways and esophagus were observed. In the gastric contents, which had a pungent smell and a greenish-brown color, 5.00 g/L of propanil, 1.27 g/L of carbaryl, 0.38 g/L of ethylbenzene, and 0.32 g/L of xylene were detected. In the blood (serum), 21.6 mg/L of propanil, 8.1 mg/L of carbaryl, 1.7 mg/L of ethylbenzene, and 4.0 mg/L of xylene were identified. Postmortem methemoglobinemia (45%) was recognized. The cause of death was considered to have been pesticide poisoning; propanil was probably most responsible for his death. The police considered the case to be "death with illness as the suspected cause." By performing an autopsy, however, we were able to clarify that the cause of death was pesticide poisoning.

Carbaryl↗

PubMed1970

Herbicide transformation. I. Studies with whole cells of Fusarium solani.

A strain of Fusarium solani isolated from soil by enrichment techniques used propanil (3', 4'-dichloropropionanilide) as a sole source of organic carbon and energy for growth in pure culture. The primary product of the transformation of propanil by F. solani was isolated and identified as 3,4-dichloroaniline (DCA). This compound accumulated in the medium to a level (80 mug/ml) which stopped further herbicide utilization. Herbicide utilization by F. solani was influenced by various environmental and nutritional factors. It was more sensitive to acid than alkaline pH. Added glucose and yeast extract increased the rate of propanil decomposition, and the reduced aeration retarded growth of the fungus and herbicide utilization. The growth of F. solani on propionate was inhibited by added DCA.

Anilides↗

PubMed1997

Acute and chronic toxicity of the herbicide Stam M-4 in field and laboratory exposures.

Propanil (3',4'-dichloropropionanilide), the active ingredient in the herbicide Stam M-4, is possibly the most extensively used herbicide for rice production in the world. Propanil and its metabolites are transported within characteristic ditch ecosystems in the production landscape of northeast Arkansas. Runoff from these ditch ecosystems is further transported to a river or other water body supplied by the Mississippi River Alluvial aquifer. Forty-eight-hour acute toxicity tests with Ceriodaphnia dubia (cladoceran) and Pimphales promelas (fathead minnow) were conducted on stormwater runoff, laboratory synthetic water, and irrigation (ground) water. No effects on survival were observed in this study following 48-h toxicity testing with the stormwater. Survival studies indicated assimilative capacity in irrigation (ground) water as opposed to laboratory synthetic water. Mean 48-h LC50s of C. dubia increased from 2.94 mg/L Stam M-4 in laboratory synthetic water to 8.01 mg/L Stam M-4 in irrigation water. Likewise, P. promelas mean 48-h LC50s increased from 23.76 (laboratory synthetic water) to 33.52 mg/L Stam(R)M-4 (ground water). In 7-d chronic tests, there was an increase in mean LC50s of C. dubia when comparing synthetic water to irrigation water (0.48 to 1.24 mg/L Stam M-4, respectively). P. promelas, however, had less tolerance for Stam M-4 in irrigation water (4.45 mg/L) than in synthetic water (5.93 mg/L) in 7-d chronic toxicity tests. Forty-eight-hour toxicity tests indicate that ground water affords organisms some assimilative capacity that laboratory synthetic water does not. Since herbicides and most other pesticides are manufactured to elicit rapid responses, 48-h toxicity results best describe potential nontarget organism effects in aquatic ecosystems.

Herbicides↗

PubMed2001

Cyanobacteria in Uruguayan rice fields: diversity, nitrogen fixing ability and tolerance to herbicides and combined nitrogen.

It has been established that cyanobacteria play a vital role in the maintenance of flooded rice field fertility. To evaluate the potential use of nitrogen-fixing cyanobacteria as a natural biofertilizer for rice in Uruguay, the diversity, abundance and nitrogen fixing ability of these microorganisms were studied in the field and in the laboratory. The effect of urea fertilization on population density and diversity of heterocystous cyanobacteria was determined on a 3-year assay. The highest number of cyanobacteria, 1.6x10(4) CFU x m(-2), was found at the control 8 weeks after flooding. About 90% of the heterocystous cyanobacteria found in both treatments belong to the genera Nostoc and Anabaena. Maximal nitrogenase activity was reached after 12 weeks of flooding in both treatments, with an average of about 20 micromol C2H4 x m(-2) x h(-1). To improve the understanding of the environmental factors that can limit nitrogenase activity in rice fields, two of the most abundant cyanobacteria isolates were tested for tolerance to combined nitrogen and two herbicides. In both isolates 0.2 mM ammonium inhibited nitrogenase activity after 24 h of culture. The addition of field-recommended doses of quinclorac and propanil affected oxygen photoevolution but nitrogenase activity was only inhibited by propanil.

Acetylene↗

PubMed1976

A comparison of electron-capture GLC, electrolytic-conductivity GLC and UV-absorption HPLC for the analysis of some herbicides in foods.

A comparison of gas chromatography with electron-capture or electrolytic-conductivity (nitrogen mode) detection, and high-pressure liquid chromatography (HPLC) with UV-absorption detection (254 nm) was carried out for the analysis of several herbicides in foods. Linuron, propanil, terbacil, benzoylprop-ethyl, and the fungicide DCNA in samples of cabbage, corn, potato, and wheat spiked at 2 and 0.2 ppm were examined. The pesticides were extracted with acetone, partitioned into petroleum ether-methylene chloride, and cleaned up on a 2% deactivated Florisil column before direct chromatographic analysis. Electron-capture gas-liquid chromatography (GLC) was most suitable for DCNA and benzoylprop-ethyl while UV-absorption HPLC was best for terbacil analysis. Linuron and propanil gave similar results for both electron-capture GLC and HPLC. Electrolytic-conductivity GLC could detect all pesticides at the 0.2 ppm level and exhibited the least number of extraneous peaks in the chromatograms.

Aniline Compounds↗

PubMed2000

Use of the Drosophila wing spot test in the genotoxicity testing of different herbicides.

Four herbicides, namely propanil, maleic hydrazide, glyphosate, and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), were investigated for genotoxicity in the wing spot test of Drosophila melanogaster. The herbicides were administered by chronic feeding to 3-day-old larvae. Two different crosses, a standard (ST) and a high-bioactivation (HB) cross, involving the flare-3 (flr(3)) and the multiple wing hairs (mwh) markers, were used. The HB cross uses flies characterized by an increased cytochrome P-450-dependent bioactivation capacity, which permits a more efficient biotransformation of promutagens and procarcinogens. In both crosses, the wings of the two types of progeny, which are inversion-free marker heterozygotes and balancer heterozygotes, were analyzed. Maleic hydrazide and glyphosate proved to be more genotoxic in the ST cross, whereas propanil appeared to be slightly more genotoxic in the HB cross. On the other hand, the herbicide 2,4,5-T increased the mutation frequency for only the small single spots in the ST cross.

2,4,5-Trichlorophenoxyacetic Acid↗

PubMedDate not supplied

Biodegradation: selection of suitable model.

Biodegradation of five herbicides, two acetanilides (propanil and propachlor), and three phenylureas (diuron, monuron, and fenuron) was analyzed in samples of river water during a period of 6-8 weeks. Concentrations of 0.2-5.0 mg/liter of the herbicides were used for biodegradation. Two types of river water samples with different numbers of microorganisms were collected from the Neris River: upstream and downstream of the city of Vilnius. The initial concentration of microorganisms varied from 4.7 x 10(5) to 2.7 x 10(6) cells/liter and from 1.4 x 10(8) to 5.3 x 10(8) cells/liter in water samples from the Neris River upstream and downstream of Vilnius, respectively. Chemical analysis was performed by the HPLC technique, using standards of herbicides and likely degradation products. Chemical parameters of different river water samples used in biodegradation experiments were analyzed. A second-order reaction rate model was used for the analysis of biodegradation data. Values of the first-order rate constants (Ka) revealed the following decrease in the biodegradation rate of herbicides: propanil >> diuron > or = monuron = propachlor > fenuron. This sequence was constant for all water samples analyzed. The set of decreasing value of second-order biodegradation rate constants (Kb) differed from the set of first-order constants (Ka) because the total number of bacteria in the water samples varied by up to two orders of magnitude, and this variation influenced the calculated values of Kb. Thus, different sets of Kb values were obtained for the water samples from the river upstream and downstream of the city. Schemes of a variety of biodegradation models are presented, and the suitability of the second-order reaction rate model for the description of biodegradation of xenobiotics is discussed.

Biodegradation, Environmental↗

PubMed2006

Compliance analysis of phenylurea and related compounds in drinking water by liquid chromatography/electrospray ionization/mass spectrometry coupled with solid-phase extraction.

A liquid chromatography/electrospray ionization/mass spectrometry method was reported for the compliance analysis of seven phenylurea compounds and two related herbicides (tebuthiuron and propanil) in drinking water. The volumes of the sample and final extract used in the method were 500 mL and 10 mL, respectively. The obtained method detection limits were less than 0.03 microg/L, and the mean recoveries were 74-128% with a relative standard deviation of 2.6-8.3% for all the studied compounds. The peak-to-peak signal-to-noise ratios ranged from 3.3 for cis-siduron to 34.2 for fluometuron. The accuracy and precision resulting from reagent and drinking water samples fortified at higher concentration levels were similar to these results. Several analytes were detected in the drinking water samples, including tebuthiuron at 0.5 microg/L, propanil at 0.7 microg/L, diuron at 0.1-2.1 microg/L, and linuron at 0.1-0.8 microg/L.

Calibration↗

PubMed2007

The use of Chironomus riparius larvae to assess effects of pesticides from rice fields in adjacent freshwater ecosystems.

A bioassay with Chironomus riparius larvae, using larval development and growth as endpoints, was carried out inside a rice field and in the adjacent wetland channel in Portugal, during pesticide treatments (molinate, endosulfan and propanil) to determine impact caused by pesticide contamination in freshwater ecosystems. The bioassay was also performed under laboratory conditions, to assess whether in situ and laboratory bioassays demonstrated comparable results. Growth was inhibited by concentrations of endosulfan (2.3 and 1.9 microgL(-1) averages) in water from rice field in both the field and laboratory, and by concentrations of endosulfan (0.55 and 0.76 microgL(-1) averages) in water from the wetland channel in the laboratory bioassay, while development was not affected. C. riparius larvae were not affected by molinate and propanil concentrations. The results indicate that endosulfan treatments in rice fields may cause an ecological impairment in adjacent freshwater ecosystems. The results also indicate that laboratory testing can be used to assess in situ toxicity caused by pesticide contamination.

Animals↗

PubMed2000

Adsorption-desorption studies of selected herbicides in soil-Fly ash mixtures.

Fly ash and soil mixtures with a range of fly ash content from 0 to 100% were used to study the adsorption and desorption of herbicides atrazine, propazine, prometryne, propanil, and molinate in batch experiments. The isotherms shapes according to Giles classification (Giles et al., 1960) were S, L, and H as the substrate changed from sandy clay loam (SCL) to fly ash, depending on the percent of fly ash in the mixture. The adsorption isotherms fit the Freundlich equation x/m = K(f) C(1/)(n)(). The K(f) values increase with the increase of the fly ash content. The mean percent amounts of herbicides, for a range of concentration 1-20 mg L(-)(1), adsorbed on the soil were 21.9% for atrazine, 50.7% for propazine, 29.04% for prometryne, 43.14% for molinate, 31.35% for propachlor, and 46.34% for propanil. Mass balance estimations show that the adsorbed amounts of the herbicides increase along with the fly ash content in the sorbent mixture and reach the 99% in the "pure" fly ash. In contrast, the amounts desorbed with water decrease as the fly ash content increases. The n values ranged from 0.82 to 3.05 indicating that the carbon content of fly ash plays a significant role during the sorption process and an increase of heterogenity of solid substrate. The increase of the amounts desorbed with acetone indicates that the sorption of organic compounds onto fly ash is believed to occur principally via the weak induction forces of London or dispersion forces which are characteristic of the physical adsorption process. The results of this research demonstrate that the fly ash shows a significant capacity for adsorption of organic compounds from aqueous solution.

Adsorption↗

PubMed1970

Herbicide transformation. II. Studies with an acylamidase of Fusarium solani.

Replacement cultures liberated 3,4-dichloroaniline (DCA) from 3,4-dichloropropionanilide (propanil). The kinetics of the conversion suggest a requirement for de novo enzyme synthesis, but the system was not influenced by chloramphenicol or puromycin. Enzyme activity was detected when acetanilide (K(m) = 0.195 mm) was used to replace propanil as substrate. Fungal acylamidase (E.C. 3.5.1., an aryl acylamine amidohydrolase) was concentrated by salt precipitation and characterized. The Fusarium solani acylamidase exhibited an optimum at pH 7.5 to 9.0 and was inactivated in 10 min at 50 C. The enzyme was not sensitive to methyl-carbamate or organophosphate insecticides, but the herbicide, Ramrod (N-isopropyl-2-chloroacetanilide), acted as a competitive inhibitor of acetanilide hydrolysis (K(i) = 0.167 mm). Hydrolysis rates were decreased by various para substitutions of acetanilide. Chloro substitution in the acyl moiety of acetanilide also reduced the rate of hydrolysis. 3,4-Dichloroacetanilide was less susceptible to enzyme action than acetanilide, but 3,4-dichloropropionanilide was hydrolyzed much more rapidly than propionanilide. The fungal acylamidase was highly specific for N-acetylarylamines. It did not catalyze hydrolysis of formanilide, butyranilide, dicryl, Karsil, fenuron, monuron, or isopropyl-N-phenylcarbamate. It appears to differ from acylamidases that have been isolated from rice, rat liver, chick kidney, and Neurospora.

Acetanilides↗

PubMed1985

The effects of selected rice and soybean pesticides on the eggs of Psorophora columbiae.

Twenty-five pesticides used in the production of rice and soybeans in Texas were tested in the laboratory to determine their toxicity to the eggs of Psorophora columbiae. A reduction in hatching rate occurred when eggs were treated with a herbicide formulation containing thiobencarb and with one containing a tank mixture of propanil and molinate. A carbaryl formulation induced hatching of eggs prior to their exposure to the hatching stimulus. Reduced survival to second instar of larvae hatching from treated eggs was observed with insecticide formulations of acephate, carbofuran, malathion, methyl parathion and toxaphene; a fungicide formulation of triphenyltin hydroxide and the tank mixture of the herbicides, propanil and molinate.

Animals↗

PubMedDate not supplied

Glutathione depletion induced in rat liver fractions by seven pesticides.

Glutathione (GSH) plays a central role in the chemical detoxication. Xenobiotics which induce GSH depletion, either via GSH conjugation or via oxidation of GSH to glutathione disulfide (GSSG), alter the mechanism of natural cellular defence against toxicants. The aim of this study was to evaluate the ability of seven widely used pesticides (Alachlor, Atrazine, Benomyl, Captan, Linuron, Methyl Parathion and Propanil) and/or of their metabolites to deplete GSH in rat liver fractions. In our experimental conditions, Atrazine, Linuron and Propanil failed to interact with rat liver GSH. Conversely, Alachlor, Benomyl and Methyl Parthion were able to deplete GSH in rat liver, probably by forming GSH conjugates. The fungicide Captan rapidly reduced the rat liver concentration of GSH by converting it to the oxidized form GSSG. But a longer incubation of Captan with rat hepatic enzymes produced the formation of metabolites which depleted GSH via conjugation. Our results suggest that exposure to the pesticides Alachlor, Benomyl, Captan and Methyl Parathion may induce an alteration of natural mechanisms of defence against toxicants in mammals, including humans.

Amino Acid Sequence↗

PubMed1999

Analysis of some pesticides in water samples using solid-phase microextraction-gas chromatography with different mass spectrometric techniques.

A solid-phase microextraction (SPME)-GC procedure has been developed for the analysis of four selected pesticides (propanil, acetochlor, myclobutanil and fenoxycarb) in water samples. Mass spectrometry (MS) was used and two different instruments, a quadrupole MS system and an ion trap operating in the MS-MS mode, were compared. A Carbowax-divinylbenzene SPME fiber was used. The performances of the two GC-MS instruments were comparable in terms of linearity (in the range of 0.1-10 microg/l in water samples) and sensitivity (limits of detection were in the low ng/l range); the quadrupole MS instrument gave better precision than the ion trap MS-MS system, but generally the relative standard deviations for replicates were acceptable for both instruments (<15%). Specificity with these two instruments was comparable in the analysis of ground water samples. Recovery tests were made to assess the applicability of the SPME procedure in the quantitative analysis of contaminated groundwaters.

Carbamates↗

PubMed2001

Determination of dichloroanilines in human urine by GC-MS, GC-MS-MS, and GC-ECD as markers of low-level pesticide exposure.

Methods for the determination of 3,4-dichloroaniline (3,4-DCA) and 3,5-dichloroaniline (3,5-DCA) as common markers of eight non-persistent pesticides in human urine are presented. 3,5-DCA is a marker for the exposure to the fungicides vinclozolin, procymidone, iprodione, and chlozolinate. Furthermore the herbicides diuron, linuron, neburon, and propanil are covered using their common marker 3,4-DCA. The urine samples were treated by basic hydrolysis to degrade all pesticides, metabolites, and their conjugates containing the intact moieties completely to the corresponding dichloroanilines. After addition of the internal standard 4-chloro-2-methylaniline, simultaneous steam distillation extraction (SDE) followed by liquid-liquid extraction (LLE) was carried out to produce, concentrate and purify the dichloroaniline moieties. Gas chromatography (GC) with mass spectrometric (MS) and tandem mass spectrometric (MS-MS) detection and also detection with an electron-capture detector (ECD) after derivatisation with heptafluorobutyric anhydride (HFBA) were employed for separation, detection, and identification. Limit of detection of the GC-MS-MS and the GC-ECD methods was 0.03 and 0.05 microg/l, respectively. Absolute recoveries obtained from a urine sample spiked with the internal standard, 3,5-, and 3,4-DCA, ranged from 93 to 103% with 9-18% coefficient of variation. The three detection techniques were compared concerning their performance, expenditure and suitability for their application in human biomonitoring studies. The described procedure has been successfully applied for the determination of 3,4- and 3,5-DCA in the urine of nonoccupationally exposed volunteers. The 3,4-DCA levels in these urine samples ranged between 0.13 and 0.34 microg/g creatinine or 0.11 and 0.56 microg/l, while those for 3,5-DCA were between 0.39 and 3.33 microg/g creatinine or 0.17 and 1.17 microg/l.

Aminoimidazole Carboxamide↗

PubMed2000

Modeling and predicting selected immunological effects of a chemical stressor (3,4-dichloropropionanilide) using the area under the corticosterone concentration versus time curve.

Many chemicals and drugs can induce a neuroendocrine stress response that can be immunosuppressive. Mathematical models have been developed that allow prediction of the immunological impact of such stress responses in mice on the basis of exposure to the important stress-related mediator corticosterone. The area under the corticosterone concentration vs. time curve (AUC) has been used as an indicator of cumulative corticosterone exposure in these modeling studies. In the present study, an immunotoxicant known to induce a stress response, 3,4-dichloropropionanilide (propanil), was evaluated to determine if corticosterone AUC values are related to suppression of immunological parameters in mice treated with this chemical. Linear relationships between corticosterone AUC values and suppression of the following parameters were noted in B6C3F1 female mice: thymus cellularity and thymus subpopulation percentages, splenic subpopulation percentages, natural killer cell activity, MHC class II protein expression, and IgG1 and IgG2a antibody responses to antigen. Linear models derived in previous studies using mice treated with exogenous corticosterone or with restraint stress effectively predicted the immunological effects of 3, 4-dichloropropionanilide on the basis of corticosterone AUC values. The models derived using immobilization stress were more effective (r(2) for observed vs. predicted = 0.90) than the models derived using mice treated with exogenous corticosterone (r(2) for observed vs. predicted = 0.65). This was expected, because most stressors induce a variety of immunomodulatory mediators, not just corticosterone. These findings have implications for risk assessment in immunotoxicology.

Animals↗

PubMed2004

Modeling and predicting stress-induced immunosuppression in mice using blood parameters.

Previous studies have shown that the area under the corticosterone concentration vs. time curve (AUC) can be used to model and predict the effects of restraint stress and chemical stressors on a variety of immunological parameters in the mouse spleen and thymus. In order to complete a risk assessment parallelogram, similar data are needed with blood as the source of immune system cells, because this is the only tissue routinely available from human subjects. Therefore, studies were conducted using treatments for which the corticosterone AUC values are already known: exogenous corticosterone, restraint, propanil, atrazine, and ethanol. Immunological parameters were measured using peripheral blood from mice treated with a series of dosages of each of these agents. Flow cytometry was used to quantify MHC II, B220, CD4, and CD8 cells. Leukocyte and differential counts were done. Spleen cell number and NK cell activity were evaluated to confirm similarity to previous studies. Immune parameter data from mouse blood indicate that MHC II expression has consistent quantitative relationships to corticosterone AUC values, similar to but less consistent than those observed in the spleen. Other immune parameters tended to have greater variability in the blood than in the spleen. The pattern observed in the spleen in which the chemical stressors generally produced very similar effects as noted for restraint stress (at the same corticosterone AUC values) was not observed for blood leukocytes. Nevertheless, MHC class II expression seems to provide a reasonably consistent indication of stress exposure in blood and spleen.

Animals↗

PubMed1982

[Microbial side chain splitting of phenylurea and carbonic acid anilides].

A Gram- negative rod-shaped bacterium 28/1 isolated by enrichment cultures is able to hydrolyze the amide bond of some phenylurea herbicides and acid anilide herbicides by an inducible amidase. 7.5% of 0.3 mumol.ml-1 linuron (3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea) are hydrolyzed after 16 hours. 1,1-Dimethylphenylureas are not degraded. Acid anilides are hydrolyzed at a higher rate, 80% of 0.5 mumol.ml-1 N-(4-chlorophenyl)-propionamide and N-(4-nitrophenyl)-propionamide are transformed after 6 hours. The 1-methoxy-1-methyl phenylureas are effective inducers. Linuron-induced cells have a specific activity of 3-4 nmol per mg dry weight per min on the substrate N-(3,4-dichlorophenyl)-propionamide (Propanil). The rate of hydrolysis is influenced by substituents of the aniline ring and by the structure of the side chain of the acid anilides.

Amidohydrolases↗