ContaminantDB: Dichlorvos

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:21 UTC

Update Date

2026-04-14 18:14:47 UTC

Accession Number

CHEM000209

Identification

Common Name

Dichlorvos

Class

Small Molecule

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 (1, 2).

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2B
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Food Toxin
Household Toxin
Insecticide
Metabolite
Organic Compound
Organochloride
Organophosphate
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,2-Dichloroethenyl dimethyl phosphate	ChEBI
DDVP	ChEBI
Dimethyl 2,2-dichlorovinyl phosphate	ChEBI
Dimethyl-2,2-dichlorovinyl phosphate	ChEBI
Phosphoric acid, 2,2-dichloroethenyl dimethyl ester	ChEBI
Phosphoric acid, 2,2-dichlorovinyl dimethyl ester	ChEBI
Atgard	Kegg
2,2-Dichloroethenyl dimethyl phosphoric acid	Generator
Dimethyl 2,2-dichlorovinyl phosphoric acid	Generator
Dimethyl-2,2-dichlorovinyl phosphoric acid	Generator
Phosphate, 2,2-dichloroethenyl dimethyl ester	Generator
Phosphate, 2,2-dichlorovinyl dimethyl ester	Generator
Dichlofos	MeSH
Dichlorophos	MeSH
Dimethyl dichlorovinyl phosphate	MeSH
Divipan	MeSH
Novotox	MeSH
Phosphoric acid 2,2 dichloroethenyl dimethyl ester	MeSH
Phosphoric acid 2,2-dichloroethenyl dimethyl ester	MeSH
2,2-Dichloroethenol dimethyl phosphate	HMDB
2,2-Dichloroethenyl phosphoric acid dimethyl ester	HMDB
2,2-Dichlorovinyl alcohol dimethyl phosphate	HMDB
2,2-Dichlorovinyl dimethyl phosphate, 8ci	HMDB
2,2-Dichlorovinyl dimethyl phosphoric acid ester	HMDB
2,2-Dichlorovinyl-O,O-dimethyl phosphate	HMDB
2,2-Dimethyldichlorovinyl phosphate	HMDB
Algard	HMDB
Apavap	HMDB
Aquaguard	HMDB
Astrobot	HMDB
Benfos	HMDB
Bibesol	HMDB
Brevinyl	HMDB
Canogard	HMDB
Cekusan	HMDB
Chlorvinphos	HMDB
Cyanophos	HMDB
Cypona	HMDB
DDVP (Insecticide)	HMDB
Dichloroethenyl dimethyl phosphate	HMDB
Diclorvos	HMDB
Dimethyl 2,2-dichloroethenyl phosphate	HMDB
Dimethyl O,O-dichlorovinyl-2,2-phosphate	HMDB
Dimethyldichlorovinyl phosphate	HMDB
Duravos	HMDB
Equigand	HMDB
Equigard	HMDB
Equigel	HMDB
Equiguard	HMDB
Ethenol, 2,2-dichloro-, dimethyl phosphate	HMDB
Fecama	HMDB
Herkal	HMDB
Herkol	HMDB
Insectigas D	HMDB
Krecalvin	HMDB
Lindan	HMDB
Lindanmafu	HMDB
Nerkol	HMDB
Nogos	HMDB
NSC 6738	HMDB
Nuvan	HMDB
O,O-Dimethyl 2,2-dichlorovinyl phosphate	HMDB
O,O-Dimethyl dichlorovinyl phosphate	HMDB
O-(2,2-Dichloroethenyl) O,O-dimethyl phosphate, 9ci	HMDB
O-(2,2-Dichlorvinyl)-O,O-dimethylphosphate	HMDB
Panaplate	HMDB
Phosphoric acid 2,2-dichlorovinyl dimethyl ester	HMDB
Phosvit	HMDB
Tetravos	HMDB
Topanol	HMDB
Unifos	HMDB
Unitox	HMDB
Vapona	HMDB
Verdican	HMDB
Verdipor	HMDB
Verdisol	HMDB

Chemical Formula

C₄H₇Cl₂O₄P

Average Molecular Mass

220.976 g/mol

Monoisotopic Mass

219.946 g/mol

CAS Registry Number

62-73-7

IUPAC Name

2,2-dichloroethenyl dimethyl phosphate

Traditional Name

dichlorvos

SMILES

COP(=O)(OC)OC=C(Cl)Cl

InChI Identifier

InChI=1S/C4H7Cl2O4P/c1-8-11(7,9-2)10-3-4(5)6/h3H,1-2H3

InChI Key

OEBRKCOSUFCWJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Dialkyl phosphates

Alternative Parents

Substituents

Dialkyl phosphate
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine acaricide (CHEBI:34690 )
dialkyl phosphate (CHEBI:34690 )
organophosphate insecticide (CHEBI:34690 )
alkenyl phosphate (CHEBI:34690 )
Organophosphorus insecticides (C14430 )
a small molecule (CPD-10185 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Liquid

Appearance

Colorless liquid.

Experimental Properties

Property	Value
Melting Point	-60°C
Boiling Point	> 184°C (363°F )
Solubility	8 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	9.77 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.37	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-9.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.19 m³·mol⁻¹	ChemAxon
Polarizability	16.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-1900000000-09877a8cb478a3cc6839	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-1900000000-09877a8cb478a3cc6839	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-7950000000-d8cdc825bf993c643600	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-0900000000-f98de9faf1be0bb7aa83	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-0900000000-93c62701332435cee993	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-0900000000-f922e6ba3c6c6b90775a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-1900000000-40a51b0033ce31d71432	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-1900000000-9ef61f0d99a23257c13d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-3900000000-c65f2474371722a3bcc8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00fr-0690000000-26446ccc45ba04ecd6a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-0930000000-5337a3d357153a9b46f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-0900000000-65501644b18b2b26ba71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-2900000000-051c8cc88647cdf4959e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-4900000000-dccb667225335d52f6d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-6900000000-8c14f2901d28ffb6e55a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0900000000-cc2455ee44a59b12a9f4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-2900000000-c792ae223d6916b397d8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4l-0900000000-ca0ee2a0d7d29061a4c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052f-0900000000-347f95538a81149f9317	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-0930000000-62f725b3cb5b2d33fd64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-001i-0900000000-f922e6ba3c6c6b90775a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-004i-0900000000-a16d9953cbbf3ee35661	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-e298d1b1b9fbe49cdf07	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0290000000-d903963507fb14645616	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-7920000000-49744b7423eca8f5c83d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0390000000-739bd76ae4f970ffb5dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1970000000-20c951792dc55918ff70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fai-4900000000-f04c27c6490895d5cc16	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-7900000000-0efae19e253ed849b729	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (7) ; inhalation (7) ; dermal (7)

Mechanism of Toxicity

Dichlorvos is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

Metabolism

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Toxicity Values

LD50: 56 mg/kg (Oral, Rat) (6) LC50: 198 mg/m3 (Inhalation, Rat) (6) LD50: 205 mg/kg (Dermal, Rabbit) (6)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (3)

Uses/Sources

Organophosphates are used in agriculture, in the home, in gardens, and in veterinary practice. (7)

Minimum Risk Level

Not Available

Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Symptoms

The effects of organophosphate poisoning are recalled using the mnemonic SLUDGEM (Salivation, Lacrimation, Urination, Diaphoresis (or Defecation), Gastrointestinal motility, Emesis, Miosis). (5)

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Concentrations

Not Available

External Links

DrugBank ID

DB11397

HMDB ID

HMDB0033956

FooDB ID

FDB012175

Phenol Explorer ID

Not Available

KNApSAcK ID