Dimethoate
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Basic Info
| Common Name | Dimethoate(F03442) |
| 2D Structure | |
| Description | Dimethoate is an organophosphate insecticide used to kill mites and insects systemically and on contact. It is used against a wide range of insects, including aphids, thrips, planthoppers and whiteflies on ornamental plants, alfalfa, apples, corn, cotton, grapefruit, grapes, lemons, melons, oranges, pears, pecans, safflower, sorghum, soybeans, tangerines, tobacco, tomatoes, watermelons, wheat and other vegetables. It is also used as a residual wall spray in farm buildings for house flies. Dimethoate has been administered to livestock for control of botflies. Dimethoate is moderately toxic and severe poisoning affects the central nervous system. (L1188) |
| FRCD ID | F03442 |
| CAS Number | 60-51-5 |
| PubChem CID | 3082 |
| Formula | C5H12NO3PS2 |
| IUPAC Name | 2-dimethoxyphosphinothioylsulfanyl-N-methylacetamide |
| InChI Key | MCWXGJITAZMZEV-UHFFFAOYSA-N |
| InChI | InChI=1S/C5H12NO3PS2/c1-6-5(7)4-12-10(11,8-2)9-3/h4H2,1-3H3,(H,6,7) |
| Canonical SMILES | CNC(=O)CSP(=S)(OC)OC |
| Isomeric SMILES | CNC(=O)CSP(=S)(OC)OC |
| Wikipedia | Dimethoate |
| Synonyms |
Aadimethoal
Phosphamid
dimethoate
Phosphamide
60-51-5
Rogor
Fosfamid
Fosfotox
Perfecthion
Perfekthion
|
| 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 s-ester - Dithiophosphate o-ester - Carboxamide group - Secondary carboxylic acid amide - Sulfenyl compound - Organothiophosphorus compound - Carboxylic acid derivative - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Carbonyl group - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen 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 | 229.249 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Complexity | 191 |
| Monoisotopic Mass | 229 |
| Exact Mass | 229 |
| XLogP | 0.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| 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+ | 0.9903 |
| Human Intestinal Absorption | HIA+ | 0.9916 |
| Caco-2 Permeability | Caco2- | 0.5363 |
| P-glycoprotein Substrate | Non-substrate | 0.8379 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8033 |
| Non-inhibitor | 0.9898 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9312 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6717 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7250 |
| CYP450 2D6 Substrate | Non-substrate | 0.7973 |
| CYP450 3A4 Substrate | Substrate | 0.5159 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7207 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7943 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9169 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7308 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8404 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9902 |
| Non-inhibitor | 0.9235 | |
| AMES Toxicity | AMES toxic | 0.7852 |
| Carcinogens | Non-carcinogens | 0.5908 |
| Fish Toxicity | Low FHMT | 0.7762 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6309 |
| Honey Bee Toxicity | High HBT | 0.8933 |
| Biodegradation | Not ready biodegradable | 0.8421 |
| Acute Oral Toxicity | II | 0.7671 |
| Carcinogenicity (Three-class) | Non-required | 0.7097 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.5332 | LogS |
| Caco-2 Permeability | 0.9033 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.5514 | LD50, mol/kg |
| Fish Toxicity | 1.8134 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3249 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Poultry - Fat | Korea | 0.05ppm | |||
| Kiwifruit | Japan | 1ppm | |||
| Banana | Japan | 1ppm | |||
| Grape | Japan | 1ppm | |||
| Celery | CAC | 0. 5mg/kg | |||
| Limes | Britain | 0.02mg/kg | |||
| Cardoons | Britain | 0.02mg/kg | |||
| Other Leafy Brassicas | Britain | 0.02mg/kg | |||
| Other Berries | Japan | 1ppm | |||
| Japanese Plum(Including Prune) | Japan | 1ppm | |||
| Mizuna | Australia | 2mg/kg | |||
| Citrus Fruits | ICMSF | 5mg/kg | |||
| Other Umbelliferous Vegetables | Japan | 1ppm | |||
| Komatsuna(Japanese Mustard Spinach) | Japan | 1ppm | |||
| Soybeans,Dry | Japan | 1ppm | |||
| Tomato | Japan | 1.0ppm | |||
| Potato | Japan | 1.0ppm | |||
| Strawberries | Australia | 5mg/kg | |||
| Potatoes | Belgium | 0.05mg/kg | |||
| Vegetable | Austria | 1.00/0.40 mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Pesticide residues in honey bees, pollen and beeswax: Assessing beehive exposure. | Environ Pollut | 2018 Oct | 29803024 |
| Effect of temperature and selected sugars on dilute solution properties of twohairless canary seed starches compared with wheat starch. | Int J Biol Macromol | 2018 Mar | 29137998 |
| Spectral Characterization and Molecular Dynamics Simulation of Pesticides Basedon Terahertz Time-Domain Spectra Analyses and Density Functional Theory (DFT)Calculations. | Molecules | 2018 Jul 2 | 30004436 |
| Antioxidant enzyme responses to the oxidative stress due to chlorpyrifos,dimethoate and dieldrin stress in palak (Spinacia oleracea L.) and their toxicityalleviation by soil amendments in tropical croplands. | Sci Total Environ | 2018 Jul 15 | 29499539 |
| Fish can smell trace metals at environmentally relevant concentrations infreshwater. | Chemosphere | 2018 Jul | 29614402 |
| Omethoate treatment mitigates high salt stress inhibited maize seed germination. | Pestic Biochem Physiol | 2018 Jan | 29463412 |
| Residual degradation and toxicity of insecticides against Bactrocera oleae. | Environ Sci Pollut Res Int | 2018 Jan | 29047054 |
| Probabilistic dietary risk assessment of pesticide residues in foods for theGerman population based on food monitoring data from 2009 to 2014. | J Expo Sci Environ Epidemiol | 2018 Jan | 28677675 |
| Greenhouse and field-based studies on the distribution of dimethoate in cottonand its effect on Tetranychus urticae by drip irrigation. | Pest Manag Sci | 2018 Jan | 28834288 |
| Evaluation of an acute oral gavage method for assessment of pesticide toxicity interrestrial amphibians. | Environ Toxicol Chem | 2018 Feb | 28865127 |
| Ambient mass spectrometry: Direct analysis of dimethoate, tebuconazole, andtrifloxystrobin on olive and vine leaves by desorption electrospray ionizationinterface. | J Mass Spectrom | 2017 Nov | 28762560 |
| Efficacy of Chemicals for the Potential Management of the Queensland Fruit FlyBactrocera tryoni (Froggatt) (Diptera: Tephritidae). | Insects | 2017 May 9 | 28486404 |
| Evaluation of Matrix Effects in Multiresidue Analysis of Pesticide Residues inVegetables and Spices by LC-MS/MS. | J AOAC Int | 2017 May 1 | 28300025 |
| Metabonomic analysis of the protective effect of quercetin on the toxicity induced by mixture of organophosphate pesticides in rat urine. | Hum Exp Toxicol | 2017 May | 27251765 |
| Oxidized multiwalled carbon nanotubes decorated with silver nanoparticles forfluorometric detection of dimethoate. | Food Chem | 2017 Jun 1 | 28159279 |
| Surveillance of pesticide residues in fruits and vegetables from Accra Metropolismarkets, Ghana, 2010-2012: a case study in Sub-Saharan Africa. | Environ Sci Pollut Res Int | 2017 Jul | 28589271 |
| Determination of pesticide and phthalate residues in tea by QuEChERS method andtheir fate in processing. | Environ Sci Pollut Res Int | 2017 Jan | 27854062 |
| Assessing the impact of intervention strategies against Taenia soliumcysticercosis using the EPICYST transmission model. | Parasit Vectors | 2017 Feb 9 | 28183336 |
| Food safety in Thailand. 3: Pesticide residues detected in mangosteen (Garciniamangostana L.), queen of fruits. | J Sci Food Agric | 2017 Feb | 27185538 |
| Investigation of degradation and penetration behaviors of dimethoate on and inspinach leaves using in situ SERS and LC-MS. | Food Chem | 2017 Dec 15 | 28764001 |
Targets
- General Function:
- Hydroxymethylglutaryl-coa synthase activity
- Specific Function:
- This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
- Gene Name:
- HMGCS2
- Uniprot ID:
- P54868
- Molecular Weight:
- 56634.915 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
References
- Rios JC, Repetto G, Galleguillos I, Jos A, Peso AD, Repetto M: High concentrations of pralidoxime are needed for the adequate reactivation of human erythrocyte acetylcholinesterase inhibited by dimethoate in vitro. Toxicol In Vitro. 2005 Oct;19(7):893-7. Epub 2005 Aug 19. [16112538 ]
- 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:
- Transmembrane signaling receptor activity
- Specific Function:
- Thrombomodulin is a specific endothelial cell receptor that forms a 1:1 stoichiometric complex with thrombin. This complex is responsible for the conversion of protein C to the activated protein C (protein Ca). Once evolved, protein Ca scissions the activated cofactors of the coagulation mechanism, factor Va and factor VIIIa, and thereby reduces the amount of thrombin generated.
- Gene Name:
- THBD
- Uniprot ID:
- P07204
- Molecular Weight:
- 60328.72 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-type endopeptidase activity
- Specific Function:
- Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
- Gene Name:
- PLAU
- Uniprot ID:
- P00749
- Molecular Weight:
- 48507.09 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:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 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:
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
- Gene Name:
- CYP2A6
- Uniprot ID:
- P11509
- Molecular Weight:
- 56501.005 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:
- Identical protein binding
- Specific Function:
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name:
- BCHE
- Uniprot ID:
- P06276
- Molecular Weight:
- 68417.575 Da
References
- Dell'Omo G, Shore RF: Behavioral and physiological effects of acute sublethal exposure to dimethoate on wood mice, Apodemus sylvaticus. Arch Environ Contam Toxicol. 1996 Jul;31(1):91-7. [8687995 ]
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 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 ]