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International Journal of Environmental... Dec 2022Organophosphates (OPPs) are an important element of modern agriculture; however, because they are being used excessively, their residues are leaching and accumulating in...
Organophosphates (OPPs) are an important element of modern agriculture; however, because they are being used excessively, their residues are leaching and accumulating in the soil and groundwater, contaminating aquatic and terrestrial food chains. An important OPP called disulfoton is frequently used to eradicate pests from a wide range of crops, including Brazil's coffee crops. Additionally, it does not easily degrade in the environment, and as such, this compound can slowly build up in living organisms such as humans. Moreover, this compound has been classified as "extremely hazardous" by the World Health Organization. This study evaluated the degradation efficiency of disulfoton using a Fenton-like reaction catalyzed by magnetite nanoparticles and determined the toxicity of the by-products of the degradation process using the bioindicator . Further, the removal efficiency of disulfoton was determined to be 94% under optimal conditions. On the other hand, the bioassay showed different toxic, cytotoxic, genotoxic, and mutagenic outcomes even after the remediation process. In conclusion, the Fenton process catalyzed by magnetite nanoparticles presents great efficiency for the oxidation of disulfoton. However, it is important to highlight that the high degradation efficiency of the Fenton-based process was not sufficient to achieve detoxification of the samples.
Topics: Humans; Disulfoton; Oxidation-Reduction; Agriculture; Soil; Crops, Agricultural
PubMed: 36613108
DOI: 10.3390/ijerph20010786 -
Se Pu = Chinese Journal of... Feb 2022Disulfoton, an organophosphorus pesticide, is used to control cotton, beet, potato, and other seedling period aphids, leaf moths, underground pests, etc., with internal...
[Determination of disulfoton and its metabolites in agricultural products by dispersive soild phase extraction-ultra high performance liquid chromatography-tandem mass spectrometry].
Disulfoton, an organophosphorus pesticide, is used to control cotton, beet, potato, and other seedling period aphids, leaf moths, underground pests, etc., with internal absorption, killing, gastric poisoning, and fumigation. Disulfoton is a highly toxic organophosphate pesticide, which can inhibit cholinesterase activity, resulting in neurophysiological disorders by inhalation, feeding, and transdermal absorption. Disulfoton is difficult to degrade in the environment, which leads to enrichment in organisms and interference with endocrine. This compound is harmful to the ecological environment and human health. To ensure the quality and safety of food, it is important to develop a detection method for disulfoton and its metabolites in agricultural products. A reliable method based on dispersive solid phase extraction (d-SPE) with ultra high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) was developed for the determination of disulfoton and its metabolites (disulfoton sulfone, disulfoton sulfoxide, demeton-, demeton- sulfone, and demeton- sulfoxide) in agricultural products (pea, asparagus, wheat, coffee bean, and peanut). The optimal extraction method was as follows: 5.0 g the samples were extracted with acetonitrile (wheat, coffee bean, and peanut presoaked in 5 mL water) in a 50 mL centrifuge tube, followed by 10 min vortex. Before 30 s vortex, 4 g NaCl was added. After 5 min centrifugation, 1.5 mL of the supernatant was cleaned up with 50 mg octadecylsilane bonded silica (C), 50 mg primary secondary amine (PSA), and 50 mg aminopropyl (NH) adsorbents. The analytes were separated on a Thermo Syncronis C column (150 mm×2.1 mm, 5 μm) with gradient elution using water and acetonitrile at a column temperature of 40 ℃. The injection volume was 2 μL. Disulfoton and its metabolites were analyzed in multiple reaction monitoring (MRM) mode with positive electrospray ionization (ESI) for the selective quantification. Qualitative and quantitative analyses were accorded to the retention times and characteristic ion pairs with one parent ion and two fragment ions. Quantitative analysis was performed by an external standard method using matrix-matched calibration curves. All the parameters that affected the extraction efficiencies were optimized. C, PSA, and NH gave good recoveries of 87.9%-109.0%. Other adsorbents, multiwalled carbon nanotubes (MWCNTs), hydroxylated multiwalled carbon nanotubes (OH-MWCNTs), carboxylated multiwalled carbon nanotubes (COOH-MWCNTs), octylsilane bonded silica (C), strong cation exchange (SCX) and neutral alumina (-AlO), led to recoveries below 56.2%. The combination of adsorbents was also considered. Seven different combinations of 50 mg C, 50 mg PSA, and 50 mg NH were chosen for the optimization experiments. There were no obvious differences in these combinations, and the target analytes recoveries ranged from 81.0% to 109.3% with relative standard deviations (RSDs) between 0.6% and 12.5%. The matrix effect could affect the extraction efficiency. The adsorbents of 50 mg C, 50 mg PSA, and 50 mg NH showed weaker matrix effects as compared with other combinations of adsorbents in the instrument. The results for the matrix effect showed that peanuts and asparagus exceeded 20%, requiring matrix-matched calibration curves. Under the optimized conditions, disulfoton and its metabolites showed good linearities (≥0.9981) in the range of 2.0-200.0 μg/L. The average spiked recoveries of disulfoton and its metabolites in peas, asparagus, wheat, peanuts, and coffee beans ranged from 75.0% to 110.0%, with RSDs of 0.7% to 14.9%. The limits of detection (LODs) were between 0.02 and 2.0 μg/kg, and the limits of quantification (LOQs) were 5.0 μg/kg. The method was applied for the detection of 80 commercial productions, and neither disulfoton nor its metabolites were found. The proposed method is rapid, accurate, highly selective, and sensitive, and it is suitable for the simultaneous determination of disulfoton and its metabolites in grain, oil crops, vegetables, and other matrices.
Topics: Chromatography, High Pressure Liquid; Disulfoton; Humans; Nanotubes, Carbon; Organophosphorus Compounds; Pesticides; Solid Phase Extraction; Tandem Mass Spectrometry
PubMed: 35080159
DOI: 10.3724/SP.J.1123.2021.04028 -
The Journal of General Psychology Oct 1973
Topics: Acetylcholinesterase; Animal Nutritional Physiological Phenomena; Animals; Behavior, Animal; Brain; Chronic Disease; Diet; Disulfoton; Drug Tolerance; Insecticides; Learning; Male; Rats
PubMed: 4795234
DOI: 10.1080/00221309.1973.9710833 -
Fundamental and Applied Toxicology :... 1983Previous studies have shown that subchronic treatment of mice with the organophosphate insecticide, disulfoton, or the carbamate insecticide, propoxur, leads to the...
Previous studies have shown that subchronic treatment of mice with the organophosphate insecticide, disulfoton, or the carbamate insecticide, propoxur, leads to the development of tolerance to their toxicity. Tolerance to disulfoton was due to a decrease in the number of muscarinic cholinergic receptors, while tolerance to propoxur appeared to be due to an induction of hepatic microsomal enzymes. In the present study we investigated if cross-tolerance between disulfoton and propoxur would occur. Cross-tolerance was evaluated by measuring acute toxicities, cholinesterase and carboxylesterase inhibition and hypothermic and antinociceptive effects. Mice tolerant to propoxur were cross-tolerant to the hypothermic and anticholinesterase effects of disulfoton. Similarly, when mice were pretreated with the microsomal enzyme inducer, phenobarbital, the toxicity of disulfoton was decreased. Mice made tolerant to disulfoton were cross-tolerant to the organophosphate chlorpyrifos, but were more sensitive than controls to the toxicity of propoxur. The acute toxicity of the organophosphate malathion was also increased in disulfoton-tolerant mice. Propoxur is metabolized by mixed function oxidases and possibly by a carboxylesterase. While hepatic microsomal enzymes appeared to be unchanged in disulfoton-tolerant mice, brain and liver carboxylesterase activities were significantly inhibited. Pretreatment of mice with the specific carboxylesterase inhibitor triorthotolylphosphate is known to greatly potentiate the toxicity of malathion and also potentiated, to a lesser extent, the toxicity of propoxur.(ABSTRACT TRUNCATED AT 250 WORDS)
Topics: Animals; Carboxylic Ester Hydrolases; Disulfoton; Drug Tolerance; Insecticides; Mice; Mice, Inbred Strains; Mixed Function Oxygenases; Phenobarbital; Propoxur
PubMed: 6642106
DOI: 10.1016/s0272-0590(83)80024-4 -
Determination of disulfoton and its metabolites in the body fluids of a Di-Syston intoxication case.Forensic Science International Dec 1990Disulfoton and its metabolites, two sulfoxides and two sulfones, in the body fluids of a patient who had ingested Di-Syston were analyzed by FPD-GC and GC/MS. After the...
Disulfoton and its metabolites, two sulfoxides and two sulfones, in the body fluids of a patient who had ingested Di-Syston were analyzed by FPD-GC and GC/MS. After the chemicals in the extract (Fraction 1) obtained by Extrelut column extraction were analyzed, disulfoton and sulfoxides in Fraction 1 were oxidized into sulfones. The sulfones in the extract (Fraction 2) obtained by Extrelut column extraction were analyzed and the estimated concentrations of metabolite were calculated. The concentrations of disulfoton and the sum of the metabolites in the blood collected on admission were 0.093 nmol/g (25.4 ng/g) and 4.92 nmol/g (corresponding to 1.35 micrograms/g of disulfoton), respectively. These concentrations appear to indicate a severe level of disulfoton intoxication.
Topics: Aged; Chromatography, Gas; Disulfoton; Gas Chromatography-Mass Spectrometry; Gastrointestinal Contents; Humans; Male; Poisoning
PubMed: 2283138
DOI: 10.1016/0379-0738(90)90107-a -
Legal Medicine (Tokyo, Japan) Nov 2012A liquid chromatography-tandem mass spectrometry method was developed and validated for simultaneous determination of disulfoton and five of its oxidative metabolites...
Rapid determination of disulfoton and its oxidative metabolites in human whole blood and urine using QuEChERS extraction and liquid chromatography-tandem mass spectrometry.
A liquid chromatography-tandem mass spectrometry method was developed and validated for simultaneous determination of disulfoton and five of its oxidative metabolites (disulfoton-sulfoxide, disulfoton-sulfone, demeton-S, demeton-S-sulfoxide and demeton-S-sulfone) in human whole blood and urine. Extraction was undertaken using a QuEChERS method, which is commonly used in food analysis. D10-Disulfoton was used as the internal standard. Separation was carried out using a CAPCELL-PAK MG II column (35×2.0 mm i.d., 5 μm, Shiseido) with a mobile phase of 10 m mol/L ammonium formate and methanol. This method was applied in an autopsy case, and disulfoton and its oxidative metabolites were successfully detected in both blood and urine. The concentrations of disulfoton in the blood and urine were 360 and 23.8 ng/mL, respectively. There was a relatively low concentration of demeton-S in both the blood (4.0 ng/mL) and urine (45.7 ng/mL). To date, there have been no reported cases of detection of demeton-S in human samples.
Topics: Aged; Chromatography, Liquid; Disulfoton; Humans; Insecticides; Male; Suicide; Tandem Mass Spectrometry
PubMed: 22818267
DOI: 10.1016/j.legalmed.2012.06.005 -
Fundamental and Applied Toxicology :... Feb 1993These experiments examined the relationship between behavioral alterations and neurochemical changes in rats exposed repeatedly to disulfoton, an organophosphate...
These experiments examined the relationship between behavioral alterations and neurochemical changes in rats exposed repeatedly to disulfoton, an organophosphate cholinesterase inhibitor. Male Long-Evans rats were injected ip for 30 days with 0, 0.5, 1, or 2 mg/kg of disulfoton in corn oil. Clinical signs and motor activity were measured during the course of repeated exposure. Cognitive function, as measured in the Morris water maze, and passive avoidance procedures were assessed near the end of the dosing regimen. Regional brain acetylcholinesterase (AChE) activity was measured during the course of dosing while the total number of muscarinic receptors was measured at the end of the dosing regimen. Tolerance developed rapidly to the clinical signs produced by disulfoton, but not to the disulfoton-induced decrease in motor activity. Disulfoton affected the acquisition of water maze performance, but had no effect on passive avoidance acquisition or retention. Repeated exposure to disulfoton decreased brain AChE activity and the number of [3H]quinuclidinyl benzilate binding sites. These data indicate that, in spite of muscarinic receptor down-regulation that followed repeated exposure to disulfoton, animals become tolerant to only some of the functional effects produced by this chemical.
Topics: Animals; Behavior, Animal; Body Weight; Brain; Cholinesterase Inhibitors; Cognition; Disulfoton; Dose-Response Relationship, Drug; Down-Regulation; Drug Administration Schedule; Male; Motor Activity; Quinuclidinyl Benzilate; Rats; Rats, Inbred Strains; Receptors, Muscarinic; Tritium
PubMed: 8449387
DOI: 10.1006/faat.1993.1022 -
Journal of Agricultural and Food... Oct 2006The reactions of thiometon and its ethyl analogue, disulfoton, with reduced sulfur species [e.g., bisulfide (HS-), polysulfide (S(n)2-), thiophenolate (PhS-), and...
The reactions of thiometon and its ethyl analogue, disulfoton, with reduced sulfur species [e.g., bisulfide (HS-), polysulfide (S(n)2-), thiophenolate (PhS-), and thiosulfate (S2O3(2-))] were examined in well-defined aqueous solutions under anoxic conditions. The role of reduced sulfur species was investigated in the abiotic degradation of thiometon and disulfoton. Experiments at 25 degrees C demonstrated that HS-, S(n)2-, PhS-, and S2O3(2-) promoted the degradation of thiometon to a great extent while only S(n)2- and PhS- showed a small accelerating effect in the degradation of disulfoton. Reactions were monitored at varying concentrations of reduced sulfur species to obtain the second-order rate constants. The reactivity of the reduced sulfur species decreased in the following order: S(n)2- > PhS- > HS- approximately S2O3(2-). Transformation products were confirmed by standards or characterized by gas chromatography mass spectrometry. The results illustrate that multiple pathways occur in the reactions with reduced sulfur species, among which the nucleophilic attack at the alpha-carbon of the alkoxy group was the predominant pathway. Activation parameters of the reaction of thiometon and disulfoton with HS- were also determined from the measured second-order rate constants over a temperature range. DeltaH( not equal) values indicated that the reactivity of thiometon toward HS- was much greater than for disulfoton. Nucleophilic attack at the alkoxy group was more important for thiometon than disulfoton. When the measured second-order rate constants at 25 degrees C are multiplied by [HS-] and Sigma[S(n)2-] reported in saltmarsh porewaters, predicted half-lives show that reduced sulfur species present at environmentally relevant concentrations may present an important sink for thiometon in coastal marine environments.
Topics: Chemical Phenomena; Chemistry, Physical; Disulfoton; Hydrogen-Ion Concentration; Hydrolysis; Insecticides; Kinetics; Organothiophosphates; Oxidation-Reduction; Sulfur Compounds
PubMed: 17002449
DOI: 10.1021/jf061019+ -
Ecotoxicology and Environmental Safety Jun 1996Mature male rainbow trout (Oncorhynchus mykiss) were exposed for 28 days to 0, 1, 5, and 20 micrograms/liter disulfoton, i.e., to concentrations well below any...
Sublethal effects of prolonged exposure to disulfoton in rainbow trout (Oncorhynchus mykiss): cytological alterations in the liver by a potent acetylcholine esterase inhibitor.
Mature male rainbow trout (Oncorhynchus mykiss) were exposed for 28 days to 0, 1, 5, and 20 micrograms/liter disulfoton, i.e., to concentrations well below any macroscopically visible effect due to the primary acute toxic mechanism of acetylcholine esterase inhibition. In an attempt to reveal sublethal injury of disulfoton in rainbow trout, ultrastructural and stereological parameters were recorded in the liver as the central organ of xenobiotic metabolism in fish. Quantitative methods were definitely not able to replace qualitative techniques because, except for mitochondria, peroxisomes, and hepatocellular lipid inclusions, stereological analysis revealed only insignificant variations of hepatocellular components, whereas hepatocytes displayed a complex pattern of numerous delicate qualitative alterations. Effects were most evident within cisternae of the rough endoplasmic reticulum (RER), thus suggesting modifications of protein metabolism. Structural alterations included degenerative effects such as dilation and vesiculation of RER cisternae, formation of concentric RER arrays and augmentation of smooth endoplasmic reticulum, dilation of Golgi cisternae, and the development of cytoplasmic myelinated bodies as well as stacks of membranous material within mitochondria. Structural integrity and augmentation of peroxisomes and mitochondria as well as increased activity of the Golgi system were indicative of adaptive/compensative reactions following disulfoton treatment. In fact, adaptive effects seemed more pronounced than degenerative phenomena resulting in only minor disturbances in hepatocyte structure following disulfoton exposure. Because most effects had to be classified as unspecific responses to environmental or xenobiotic stressors, no distinct mode of sublethal action can be suggested for disulfoton.
Topics: Animals; Cholinesterase Inhibitors; Cytoplasm; Disulfoton; Endoplasmic Reticulum, Rough; Endoplasmic Reticulum, Smooth; Golgi Apparatus; Insecticides; Liver; Male; Microscopy, Electron; Mitochondria, Liver; Oncorhynchus mykiss; Water Pollutants, Chemical
PubMed: 8793319
DOI: 10.1006/eesa.1996.0043