Dichlorvos
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Basic Info
| Common Name | Dichlorvos(F03449) |
| 2D Structure | |
| Description | Dichlorvos is used as a household and public health fumigant, for crop protection and as an anthelmintic in animal feeds.Dichlorvos or 2,2-dichlorovinyl dimethyl phosphate (DDVP) is a highly volatile organophosphate, widely used as a insecticide to control household pests, in public health, and protecting stored product from insects. It is effective against mushroom flies, aphids, spider mites, caterpillars, thrips, and whiteflies in greenhouse, outdoor fruit, and vegetable crops. (Wikipedia) Dichlorvos has been shown to exhibit neurotransmitter and relaxant functions (A7732, A7733). |
| FRCD ID | F03449 |
| CAS Number | 62-73-7 |
| PubChem CID | 3039 |
| Formula | C4H7Cl2O4P |
| IUPAC Name | 2,2-dichloroethenyl dimethyl phosphate |
| InChI Key | OEBRKCOSUFCWJD-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H7Cl2O4P/c1-8-11(7,9-2)10-3-4(5)6/h3H,1-2H3 |
| Canonical SMILES | COP(=O)(OC)OC=C(Cl)Cl |
| Isomeric SMILES | COP(=O)(OC)OC=C(Cl)Cl |
| Wikipedia | Dichlorvos |
| Synonyms |
Divipan
dichlorvos
DDVP
62-73-7
Dichlorophos
Vapona
Chlorvinphos
Brevinyl
Canogard
Dichlorphos
|
| Classifies |
Illegal Additives
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic phosphoric acids and derivatives |
| Subclass | Phosphate esters |
| Intermediate Tree Nodes | Alkyl phosphates |
| Direct Parent | Dialkyl phosphates |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Dialkyl phosphate - Chloroalkene - Haloalkene - Vinyl halide - Vinyl chloride - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 220.97 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Complexity | 181 |
| Monoisotopic Mass | 219.946 |
| Exact Mass | 219.946 |
| XLogP | 1.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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+ | 0.9407 |
| Human Intestinal Absorption | HIA+ | 0.9801 |
| Caco-2 Permeability | Caco2- | 0.5670 |
| P-glycoprotein Substrate | Non-substrate | 0.8353 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8842 |
| Non-inhibitor | 0.9790 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9483 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7534 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8187 |
| CYP450 2D6 Substrate | Non-substrate | 0.8682 |
| CYP450 3A4 Substrate | Non-substrate | 0.5097 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7935 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8433 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9190 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6278 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8981 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8319 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8899 |
| Non-inhibitor | 0.9360 | |
| AMES Toxicity | AMES toxic | 0.9108 |
| Carcinogens | Carcinogens | 0.7405 |
| Fish Toxicity | High FHMT | 0.7290 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8842 |
| Honey Bee Toxicity | High HBT | 0.9385 |
| Biodegradation | Not ready biodegradable | 0.9342 |
| Acute Oral Toxicity | I | 0.7847 |
| Carcinogenicity (Three-class) | Danger | 0.7193 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.3467 | LogS |
| Caco-2 Permeability | 0.4947 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.0826 | LD50, mol/kg |
| Fish Toxicity | 1.0594 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0119 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Peaches (Flat peaches/saturn peaches/paraguayas, Nectarines, Other hybrids of Persica vulgaris; syn: Prunus persica, not elsewhere mentioned,) | 0140030 | European Union | 0.01* | 01/09/2008 | |
| Plums (American plums, Beach plums, Cherry plums /myrabolans, Chickasaw plums, Chinese jujubes/red dates/Chinese dates, Damsons/ bullaces, Gages/greengages/Reine Claudes, Japanese plums, Klamath pl... | 0140040 | European Union | 0.01* | 01/09/2008 | |
| Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E... | 0154010 | European Union | 0.01* | 01/09/2008 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 01/09/2008 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 01/09/2008 | |
| 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* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 01/09/2008 | |
| 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* | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.01* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.01* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.01* | 01/09/2008 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 01/09/2008 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.01* | 01/09/2008 | |
| Macadamias | 0120070 | European Union | 0.01* | 01/09/2008 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Feeding inhibition in Corbicula fluminea (O.F. Muller, 1774) as an effectcriterion to pollutant exposure: Perspectives for ecotoxicity screening andrefinement of chemical control. | Aquat Toxicol | 2018 Mar | 29328973 |
| Investigation of the Nucleophilic Attack of Dichlorvos by Reduced Sulfur Species Using 1H NMR. | J Agric Food Chem | 2018 Jan 17 | 29224357 |
| Role of induced glutathione-S-transferase from Helicoverpa armigera (Lepidoptera:Noctuidae) HaGST-8 in detoxification of pesticides. | Ecotoxicol Environ Saf | 2018 Jan | 28923727 |
| 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 |
| Enantioseparation and enantioselective behavior of trichlorfon enantiomers in sediments. | Chirality | 2017 Mar | 28321927 |
| Determination of pesticide and phthalate residues in tea by QuEChERS method andtheir fate in processing. | Environ Sci Pollut Res Int | 2017 Jan | 27854062 |
| Essential oil optimizes the susceptibility of Callosobruchus maculatus andenhances the nutritional qualities of stored cowpea Vigna unguiculata. | R Soc Open Sci | 2017 Aug 23 | 28879012 |
| Oxidative injury caused by individual and combined exposure of neonicotinoid, organophosphate and herbicide in zebrafish. | Toxicol Rep | 2017 | 28959645 |
| Residue levels of five grain-storage-use insecticides during the productionprocess of sorghum distilled spirits. | Food Chem | 2016 Sep 1 | 27041292 |
| Haematological, Biochemical and Antioxidant Changes in Wistar Rats Exposed to Dichlorvos Based Insecticide Formulation Used in Southeast Nigeria. | Toxics | 2016 Nov 29 | 29051431 |
| Determination of dichlorvos residue levels in vegetables sold in Lusaka, Zambia. | Pan Afr Med J | 2016 Mar 16 | 27279940 |
| Biodegradation of the Organophosphate Trichlorfon and Its Major DegradationProducts by a Novel Aspergillus sydowii PA F-2. | J Agric Food Chem | 2016 Jun 1 | 27161040 |
| A sensitive fluorescent sensor for selective determination of dichlorvos based onthe recovered fluorescence of carbon dots-Cu(II) system. | Food Chem | 2016 Jul 1 | 26920268 |
| Evaluation of Quechers Sample Preparation and GC Mass Spectrometry Method for theDetermination of 15 Pesticide Residues in Tomatoes Used in Salad ProductionPlants. | Iran J Public Health | 2016 Feb | 27114988 |
| Application of elevated temperature-dispersive liquid-liquid microextraction for determination of organophosphorus pesticides residues in aqueous samples followedby gas chromatography-flame ionization detection. | Food Chem | 2016 Dec 1 | 27374524 |
| Protective Effects of Intralipid and Caffeic Acid Phenethyl Ester (CAPE) onHepatotoxicity and Pancreatic Injury Caused by Dichlorvos in Rats. | Biochem Genet | 2016 Dec | 27365043 |
| Brain acetylcholinesterase of jaguar cichlid (Parachromis managuensis): Fromphysicochemical and kinetic properties to its potential as biomarker ofpesticides and metal ions. | Aquat Toxicol | 2016 Aug | 27288599 |
| Dichlorvos exposure results in large scale disruption of energy metabolism in theliver of the zebrafish, Danio rerio. | BMC Genomics | 2015 Oct 24 | 26499117 |
| Degradation of four organophosphorous pesticides catalyzed by chitosan-metalcoordination complexes. | Environ Sci Pollut Res Int | 2015 Oct | 26003089 |
Targets
- 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:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- Specific Function:
- Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
- Gene Name:
- FBF1
- Uniprot ID:
- Q8TES7
- Molecular Weight:
- 125445.19 Da
References
- Li B, Schopfer LM, Hinrichs SH, Masson P, Lockridge O: Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry assay for organophosphorus toxicants bound to human albumin at Tyr411. Anal Biochem. 2007 Feb 15;361(2):263-72. Epub 2006 Dec 4. [17188226 ]
- General Function:
- Transferrin receptor binding
- Specific Function:
- Transferrins are iron binding transport proteins which can bind two Fe(3+) ions in association with the binding of an anion, usually bicarbonate. It is responsible for the transport of iron from sites of absorption and heme degradation to those of storage and utilization. Serum transferrin may also have a further role in stimulating cell proliferation.
- Gene Name:
- TF
- Uniprot ID:
- P02787
- Molecular Weight:
- 77063.195 Da
References
- Li B, Schopfer LM, Grigoryan H, Thompson CM, Hinrichs SH, Masson P, Lockridge O: Tyrosines of human and mouse transferrin covalently labeled by organophosphorus agents: a new motif for binding to proteins that have no active site serine. Toxicol Sci. 2009 Jan;107(1):144-55. doi: 10.1093/toxsci/kfn211. Epub 2008 Oct 16. [18930948 ]
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 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:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 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:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]