Diazinon
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Basic Info
| Common Name | Diazinon(F03312) |
| 2D Structure | |
| Description | Nonsystemic insecticide for rice and fruit trees. Cholinesterase inhibitor. Diazinon is used against animal ectoparasites Diazinon has been shown to exhibit apoptotic and antibiotic functions (A7691, A7692). |
| FRCD ID | F03312 |
| CAS Number | 333-41-5 |
| PubChem CID | 3017 |
| Formula | C12H21N2O3PS |
| IUPAC Name | diethoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane |
| InChI Key | FHIVAFMUCKRCQO-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3 |
| Canonical SMILES | CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C |
| Isomeric SMILES | CCOP(=S)(OCC)OC1=NC(=NC(=C1)C)C(C)C |
| Synonyms |
diazinon
Dimpylate
333-41-5
Diazinone
Oleodiazinon
Neocidol
Ciazinon
Dassitox
Diazitol
Ektoband
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic thiophosphoric acids and derivatives |
| Subclass | Thiophosphoric acid esters |
| Intermediate Tree Nodes | Aryl thiophosphates |
| Direct Parent | Pyrimidinyl phosphorothioates |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Pyrimidinyl phosphorothioate - Thiophosphate triester - Pyrimidine - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 304.345 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Complexity | 307 |
| Monoisotopic Mass | 304.101 |
| Exact Mass | 304.101 |
| XLogP | 3.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| 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+ | 0.9623 |
| Human Intestinal Absorption | HIA+ | 0.9965 |
| Caco-2 Permeability | Caco2- | 0.5486 |
| P-glycoprotein Substrate | Non-substrate | 0.8155 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6836 |
| Non-inhibitor | 0.9968 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9118 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7216 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7520 |
| CYP450 2D6 Substrate | Non-substrate | 0.6616 |
| CYP450 3A4 Substrate | Non-substrate | 0.5139 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5378 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6426 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8985 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5590 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7960 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8359 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9680 |
| Non-inhibitor | 0.9176 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.7546 |
| Fish Toxicity | Low FHMT | 0.5095 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7625 |
| Honey Bee Toxicity | High HBT | 0.8861 |
| Biodegradation | Not ready biodegradable | 0.9184 |
| Acute Oral Toxicity | II | 0.7374 |
| Carcinogenicity (Three-class) | Non-required | 0.6941 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.7028 | LogS |
| Caco-2 Permeability | 1.1302 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.6326 | LD50, mol/kg |
| Fish Toxicity | 1.8250 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2954 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| (g) other farmed terrestrial animals (Alpaca, Bactrian camel, Capybara, Cottontail/American rabbit, Dromedary, Eland, Elk/moose, Emu, Fallow deer, Guinea pig, Hare (farmed), Llama, Nandu/greater rh... | 1017000 | European Union | 0.01* | 26/04/2013 | |
| Kidney | 1013040 | European Union | 0.03 | 26/04/2013 | |
| Wild fungi (Ceps/porcino mushrooms, Chanterelles, Hedgehog mushrooms, Horns of plenty/black trumpets, Morels, Périgord black truffles, Piemont white truffles, Saint George's mushrooms, Scotch bonne... | 0280020 | European Union | 0.01* | 26/04/2013 | |
| Others (2) | 1013990 | European Union | 0.01* | 26/04/2013 | |
| Others (2) | 0251990 | European Union | 0.01* | 26/04/2013 | |
| (b) spinaches and similar leaves | 0252000 | European Union | 0.01* | 26/04/2013 | |
| Purslanes (Agretti, Glassworts/samphires, Rock samphires, Sea asters, Sea lavenders, Winter purslanes/miner's lettuces, Karkallas/Hottentot figs/Iceplant leaves,) | 0252020 | European Union | 0.01* | 26/04/2013 | |
| Chards/beet leaves (Beetroot leaves, Swiss chards,) | 0252030 | European Union | 0.01* | 26/04/2013 | |
| Others (2) | 0252990 | European Union | 0.01* | 26/04/2013 | |
| (c) grape leaves and similar species (Climbing wattle/acacia shoots, Malabar nightshades,) | 0253000 | European Union | 0.01* | 26/04/2013 | |
| (d) watercresses (Morning glory/Chinese convolvolus/water convolvolus/kangkung, Water clovers, Water mimosas,) | 0254000 | European Union | 0.01* | 26/04/2013 | |
| (e) witloofs/Belgian endives (Dandelion leaves (forced),) | 0255000 | European Union | 0.01* | 26/04/2013 | |
| (f) herbs and edible flowers | 0256000 | European Union | 0.02* | 26/04/2013 | |
| Chervil | 0256010 | European Union | 0.02* | 26/04/2013 | |
| Chives (Chinese chives/oriental garlic/garlic chives, Ramson/wild garlic/bear's garlic,) | 0256020 | European Union | 0.02* | 26/04/2013 | |
| Celery leaves (Angelica (leaves and stems), Burnet, Caraway leaves, Coriander leaves, Culantro/false coriander leaves, Dill leaves, Fennel leaves, Fenugreek leaves, Herb of grace/rue, Lovage leaves... | 0256030 | European Union | 0.02* | 26/04/2013 | |
| Parsley (Root parsley leaves,) | 0256040 | European Union | 0.02* | 26/04/2013 | |
| Sage (Borage, Curry herb, Greek sage, Jamé's sage/Mexican sage, Other species and hybrids of genus Salvia, not elsewhere mentioned,) | 0256050 | European Union | 0.02* | 26/04/2013 | |
| Rosemary (Santolina/green lavander cotton, Green santolina,) | 0256060 | European Union | 0.02* | 26/04/2013 | |
| Thyme (Creeping thyme, Cretan oregano/Turkish oregano, Lemon savory, Lemon thyme/citrus thyme, Marjoram, Mastic thyme, Oregano, Summer savory, Syrian oregano/bible hyssop/za'atar, Winter savory,) | 0256070 | European Union | 0.02* | 26/04/2013 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Aptasensor based on fluorophore-quencher nano-pair and smartphone spectrum readerfor on-site quantification of multi-pesticides. | Biosens Bioelectron | 2018 Oct 15 | 29886189 |
| Influence of sex on biomarkers of oxidative stress in the kidney, lungs, and liver of rabbits after exposure to diazinon. | Environ Sci Pollut Res Int | 2018 Nov | 30232776 |
| Occurrence of multiclass pesticide residues in tomato samples collected fromdifferent markets of Iran. | J Environ Health Sci Eng | 2018 May 7 | 29983989 |
| Simultaneous determination of organophosphorus pesticides and phthalates in baby food samples by ultrasound-vortex-assisted liquid-liquid microextraction andGC-IT/MS. | Anal Bioanal Chem | 2018 May | 29549507 |
| Evaluation of attenuative effect of tert-butylhydroquinone againstdiazinon-induced oxidative stress on hematological indices in male Wistar rats. | Biomed Rep | 2018 Jun | 29774145 |
| Can Rice (Oryza sativa) Mitigate Pesticides and Nutrients in Agricultural Runoff? | Bull Environ Contam Toxicol | 2018 Jan | 29196795 |
| Degradation of Organophosphorus and Pyrethroid Insecticides in Beverages:Implications for Risk Assessment. | Toxics | 2018 Feb 2 | 29393904 |
| Evaluation of abamectin, diazinon and chlorpyrifos pesticide residues in appleproduct of Mahabad region gardens: Iran in 2014. | Food Chem | 2017 Sep 15 | 28449991 |
| Decline patterns and risk assessment of 10 multi-class pesticides in young sproutamaranth (Amaranthus mangostanus) under greenhouse growing conditions. | Environ Sci Pollut Res Int | 2017 Nov | 28918593 |
| Human health risk assessment of organophosphorus pesticide in rice crop fromselected districts of Anzali International Wetland basin, Iran. | Hum Exp Toxicol | 2017 May | 27417637 |
| Evaluation of residue risk and toxicity of different treatments with diazinoninsecticide applied to mushroom crops. | J Environ Sci Health B | 2017 Mar 4 | 28121277 |
| Agrochemical loading in drains and rivers and its connection with pollution in coastal lagoons of the Mexican Pacific. | Environ Monit Assess | 2017 Jun | 28510105 |
| Mitigation of atrazine, S-metolachlor, and diazinon using common emergent aquaticvegetation. | J Environ Sci (China) | 2017 Jun | 28571845 |
| Field Evaluation of Insecticides for Control of Cabbage Maggot (Diptera:Anthomyiidae) in Rutabaga in Canada. | J Econ Entomol | 2017 Feb 1 | 28031474 |
| Food safety in Thailand. 3: Pesticide residues detected in mangosteen (Garciniamangostana L.), queen of fruits. | J Sci Food Agric | 2017 Feb | 27185538 |
| Simultaneous determination of 35 ultra-trace level organophosphorus pesticideresidues in Sanjie Zhentong capsules of traditional Chinese medicine using ultra high performance liquid chromatography with tandem mass spectrometry. | J Sep Sci | 2017 Feb | 27935251 |
| Catalytic polymer-clay composite for enhanced removal and degradation of diazinon. | J Hazard Mater | 2017 Aug 5 | 28437697 |
| An evaporation-assisted dispersive liquid-liquid microextraction technique as asimple tool for high performance liquid chromatography tandem-mass spectrometrydetermination of insecticides in wine. | J Chromatogr A | 2017 Aug 25 | 28728929 |
| Simultaneous determination of pesticide residues and antioxidants in blended oil using a liquid-liquid extraction combined with dispersive solid phase extraction method. | Food Chem | 2017 Aug 15 | 28372183 |
| Preparation of magnetic mesoporous silica composite for the solid-phasemicroextraction of diazinon and malathion before their determination byhigh-performance liquid chromatography. | J Sep Sci | 2017 Apr | 28195398 |
Targets
- General Function:
- Vitamin d 24-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.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 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
- Tacal O, Lockridge O: Methamidophos, dichlorvos, O-methoate and diazinon pesticides used in Turkey make a covalent bond with butyrylcholinesterase detected by mass spectrometry. J Appl Toxicol. 2010 Jul;30(5):469-75. doi: 10.1002/jat.1518. [20229498 ]
- General Function:
- Arylformamidase activity
- Specific Function:
- Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites.
- Gene Name:
- AFMID
- Uniprot ID:
- Q63HM1
- Molecular Weight:
- 33991.5 Da
- Mechanism of Action:
- Diazoxon inhibits liver kynurenine formamidase.
References
- Seifert J, Pewnim T: Alteration of mice L-tryptophan metabolism by the organophosphorous acid triester diazinon. Biochem Pharmacol. 1992 Dec 1;44(11):2243-50. [1282004 ]
- General Function:
- Vitamin d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 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 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 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:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 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:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name:
- SULT2A1
- Uniprot ID:
- Q06520
- Molecular Weight:
- 33779.57 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 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:
- 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:
- Diazoxon the main toxic intermediate of diazinon, inhibits acetylcholinesterase in the central and peripheral nervous system. This results in the accumulation of acetylcholine, causing excessive stimulation of cholinergic fibers in the postganglionic parasympathetic nerve endings, neuromuscular junctions of the skeletal muscles, and cells of the central nervous system that results in hyperpolarization and receptor desensitization. This produces muscarinic, nicotinic, and CNS effects.
References
- ATSDR - Agency for Toxic Substances and Disease Registry (2008). Toxicological profile for diazinon. U.S. Public Health Service in collaboration with U.S. : http://www.atsdr.cdc.gov/toxprofiles/tp86.html
- 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 ]