Disulfoton
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Basic Info
| Common Name | Disulfoton(F03297) |
| 2D Structure | |
| Description | Disulfoton is a manufactured organophosphate used as a pesticide. It is used mainly in agriculture to protect field and vegetable crops. (L123) |
| FRCD ID | F03297 |
| CAS Number | 298-04-4 |
| PubChem CID | 3118 |
| Formula | C8H19O2PS3 |
| IUPAC Name | diethoxy-(2-ethylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane |
| InChI Key | DOFZAZXDOSGAJZ-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H19O2PS3/c1-4-9-11(12,10-5-2)14-8-7-13-6-3/h4-8H2,1-3H3 |
| Canonical SMILES | CCOP(=S)(OCC)SCCSCC |
| Isomeric SMILES | CCOP(=S)(OCC)SCCSCC |
| Wikipedia | Disulfoton |
| Synonyms |
disulfoton
Thiodemeton
Di-syston
298-04-4
Dithiodemeton
Dithiosystox
Glebofos
Solvigran
Solvirex
Dution
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic dithiophosphoric acids and derivatives |
| Subclass | Dithiophosphate O-esters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dithiophosphate O-esters |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Dithiophosphate o-ester - Dithiophosphate s-ester - Dialkylthioether - Sulfenyl compound - Thioether - Organothiophosphorus compound - Organic oxygen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 274.392 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 9 |
| Complexity | 168 |
| Monoisotopic Mass | 274.028 |
| Exact Mass | 274.028 |
| XLogP | 4 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9729 |
| Human Intestinal Absorption | HIA+ | 0.9970 |
| Caco-2 Permeability | Caco2+ | 0.5000 |
| P-glycoprotein Substrate | Non-substrate | 0.6960 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6571 |
| Non-inhibitor | 0.9114 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8936 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4414 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7873 |
| CYP450 2D6 Substrate | Non-substrate | 0.8363 |
| CYP450 3A4 Substrate | Non-substrate | 0.6055 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8043 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7652 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8959 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7399 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7846 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.5822 |
| Non-inhibitor | 0.7463 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Carcinogens | 0.6602 |
| Fish Toxicity | High FHMT | 0.8542 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8225 |
| Honey Bee Toxicity | High HBT | 0.9243 |
| Biodegradation | Not ready biodegradable | 0.8942 |
| Acute Oral Toxicity | I | 0.9358 |
| Carcinogenicity (Three-class) | Non-required | 0.6921 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.1674 | LogS |
| Caco-2 Permeability | 0.9408 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.9623 | LD50, mol/kg |
| Fish Toxicity | 1.6856 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1308 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ... | 0260010 | European Union | 0.01* | 26/04/2013 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.05* | 26/04/2013 | |
| Aril spices | 0870000 | European Union | 0.05* | 26/04/2013 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 26/04/2013 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 26/04/2013 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 26/04/2013 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 26/04/2013 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 26/04/2013 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 26/04/2013 | |
| Others (2) | 0110990 | European Union | 0.01* | 26/04/2013 | |
| Tree nuts | 0120000 | European Union | 0.02* | 26/04/2013 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 26/04/2013 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 26/04/2013 | |
| Cashew nuts | 0120030 | European Union | 0.02* | 26/04/2013 | |
| Chestnuts | 0120040 | European Union | 0.02* | 26/04/2013 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.02* | 26/04/2013 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.02* | 26/04/2013 | |
| Macadamias | 0120070 | European Union | 0.02* | 26/04/2013 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.02* | 26/04/2013 | |
| Pistachios | 0120100 | European Union | 0.02* | 26/04/2013 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Agrochemical loading in drains and rivers and its connection with pollution in coastal lagoons of the Mexican Pacific. | Environ Monit Assess | 2017 Jun | 28510105 |
| Dissipation kinetics of organophosphorus pesticides in milled toasted maize andwheat flour (gofio) during storage. | Food Chem | 2017 Aug 15 | 28372254 |
| Polycyclic aromatic hydrocarbons and pesticides in milk powder. | J Dairy Res | 2016 May | 27210498 |
| [Validation study on a multi-residue method for determination of pesticides inagricultural products by LC-MS/MS]. | Shokuhin Eiseigaku Zasshi | 2014 | 25743592 |
| Total diet study on pesticide residues in France: levels in food as consumed and chronic dietary risk to consumers. | Environ Int | 2012 Sep 15 | 22595191 |
| Application of the molecularly imprinted solid-phase extraction to theorganophosphate residues determination in strawberries. | Anal Bioanal Chem | 2012 Oct | 22968680 |
| Rapid determination of disulfoton and its oxidative metabolites in human wholeblood and urine using QuEChERS extraction and liquid chromatography-tandem massspectrometry. | Leg Med (Tokyo) | 2012 Nov | 22818267 |
| Development of a broad-specificity monoclonal antibody-based immunoaffinitychromatography cleanup for organophosphorus pesticide determination inenvironmental samples. | J Agric Food Chem | 2012 Jun 13 | 22612520 |
| Pesticide residue analysis in cereal-based baby foods using multi-walled carbonnanotubes dispersive solid-phase extraction. | Anal Bioanal Chem | 2012 Jul | 22623047 |
| Pesticide analysis in toasted barley and chickpea flours. | J Sep Sci | 2012 Jan | 25940740 |
| Determination of pesticides and their metabolites in processed cereal samples. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2012 | 22043870 |
| Levels and seasonal variability of pesticides in the rural atmosphere of SouthernOntario. | J Agric Food Chem | 2010 Jan 27 | 20039708 |
| Assessment of the stability of pesticides during the cryogenic processing offruits and vegetables. | Food Addit Contam | 2007 Nov | 17852403 |
| Reaction of thiometon and disulfoton with reduced sulfur species in simulatednatural environment. | J Agric Food Chem | 2006 Oct 4 | 17002449 |
| [Degradation of thiometon in ethyl acetate]. | Shokuhin Eiseigaku Zasshi | 2001 Apr | 11486375 |
| Comparative toxicity of selected organophosphate insecticides against resistantand susceptible clones of the greenbug, Schizaphis graminum (Homoptera:aphididae). | J Agric Food Chem | 2000 Oct | 11052723 |
| The effect of multiple soil applications of disulfoton on enhanced microbialdegradation in soil and subsequent uptake of insecticidal chemicals by potatoplants. | J Environ Sci Health B | 1994 May | 8201175 |
Targets
- General Function:
- Cytokine activity
- Specific Function:
- Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
- Gene Name:
- IL1A
- Uniprot ID:
- P01583
- Molecular Weight:
- 30606.29 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
- Mechanism of Action:
- The toxic metabolites of disulfoton, mainly disulfoton sulfoxide, disulfoton sulfone, demeton S-sulfoxide and demeton S-sulfone, inhibit acetylcholinesterase in nervous tissue. The inhibition of acetylcholinesterase results in the accumulation of acetylcholine at the muscarinic and nicotinic cholinergic receptors of nerve synapses, which causes an overstimulation of cholinergic nerves and effector organs.
References
- ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for disulfoton. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp65.html
- General Function:
- Type iii transforming growth factor beta receptor binding
- Specific Function:
- Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
- Gene Name:
- TGFB1
- Uniprot ID:
- P01137
- Molecular Weight:
- 44340.685 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]