Dichlorvos CAS 62-73-7
Introduction：Basic information about Dichlorvos CAS 62-73-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Dichlorvos Basic informationDescription References
| Product Name: | Dichlorvos |
| Synonyms: | MAFU(R);DDVP (dichlorvos);dichlorvos (ISO) 2,2-dichlorovinyl dimethyl phosphate;ddvp (jmaf);dichlorvos (bsi,iso,ban,esa);dichlorvos solution;Dichlorvos，DDV;DICLORPHOS |
| CAS: | 62-73-7 |
| MF: | C4H7Cl2O4P |
| MW: | 220.98 |
| EINECS: | 200-547-7 |
| Product Categories: | SURITAL;Aliphatics;Phosphorylating and Phosphitylating Agents;AcaricidesPesticides&Metabolites;Alpha sort;D;DAlphabetic;DIA - DICMethod Specific;Endocrine Disruptors (Draft)Pesticides;EPA;Insecticides;Organophorous;Pesticides;Pesticides&Metabolites;AcaricidesAlphabetic;INSECTICIDE;Herbicide |
| Mol File: | 62-73-7.mol |
Dichlorvos Chemical Properties
| Melting point | -60°C |
| Boiling point | 140°C |
| density | 1.415 |
| vapor pressure | 1.2 x 10-2 mmHg at 20 °C (quoted, Windholz et al., 1983:Kawamoto and Urano, 1989)5.27 x 10-2 mmHg at 25 °C (gas saturation method-GC, Kim et al., 1984) |
| refractive index | nD25 1.451 |
| Fp | 100 °C |
| storage temp. | 0-6°C |
| solubility | Miscible with alcohol and most nonpolar solvents (Windholz et al., 1983) |
| Water Solubility | Slightly soluble. 1 g/100 mL |
| Merck | 13,3105 |
| BRN | 1709141 |
| Henry's Law Constant | 3.38 at 10.00 °C, 3.62 at 11.00 °C, 3.73 at 12.00 °C, 5.05 at 13.00 °C, 6.99 at 15.00 °C, 10.8 at18.00 °C, 15.5 at 20.00 °C, 17.9 at 22.50 °C, 22.7 at 23.00 °C, 24.8 at 25.00 °C (dynamicequilibrium system-GC, Gautier et al., 2003) |
| Exposure limits | NIOSH REL: TWA 1 mg/m3, IDLH 100 mg/m3; OSHA PEL: TWA 1ppm; ACGIH TLV: TWA 0.1 ppm. |
| Major Application | agriculture environmental |
| InChI | 1S/C4H7Cl2O4P/c1-8-11(7,9-2)10-3-4(5)6/h3H,1-2H3 |
| InChIKey | OEBRKCOSUFCWJD-UHFFFAOYSA-N |
| SMILES | COP(=O)(OC)O\C=C(\Cl)Cl |
| NIST Chemistry Reference | Dimethyl-2,2-dichlorovinyl phosphate(62-73-7) |
| IARC | 2B (Vol. Sup 7, 53) 1991 |
| EPA Substance Registry System | Dichlorvos (62-73-7) |
Safety Information
| Hazard Codes | T;N,N,T,T+,Xn,F |
| Risk Statements | 24/25-26-43-50-28-24-36-20/21/22-11 |
| Safety Statements | 1/2-28-36/37-45-61-16 |
| OEB | C |
| OEL | TWA: 1 mg/m3 [skin] |
| RIDADR | 2786 |
| WGK Germany | 3 |
| RTECS | TC0350000 |
| TSCA | TSCA listed |
| HazardClass | 6.1(a) |
| PackingGroup | II |
| HS Code | 29199000 |
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 2 Dermal Acute Tox. 2 Inhalation Acute Tox. 2 Oral Aquatic Acute 1 Skin Sens. 1 |
| Hazardous Substances Data | 62-73-7(Hazardous Substances Data) |
| Toxicity | LD50 orally in male, female rats: 80, 56 mg/kg (Gaines) |
| IDLA | 100 mg/m3 |
| Description | Dichlorvos is a famous organophosphate insecticide that widely used to control household pests, in public health, and protecting stored product from insects. The compound has been commercially available since 1961. It can be used for the treatment of mushroom flies, aphids, spiders, caterpillars, thrips and whiteflies in fruits and crops as well as many kinds of parasitic worm in dogs and livestock as well as human beings. Its primary target, like other kinds of organophosphate insecticide, is the acetylcholinesterase. Therefore, it blocks the normal function of the nervous systems of insects. However, its application has been under controversy due to its potential toxicity on human beings and animals. Exposure to it can cause multiple adverse reactions of respiratory, cardiovascular, eye, skin, and muscle, nervous and so on. It is also known that Dichlorvos is extremely toxic to fishes, being capable of impairing fish health through impairing normal metabolism and even leading to death. |
| References | Das, Suchismita. "A review of Dichlorvos toxicity in fish." Current World Environment 8.1(2013):143-149.Booth, Ed, and E. B. Jones. "Review of the in vitro and in vivo genotoxicity of dichlorvos. " Regulatory Toxicology & Pharmacology 49.3(2007):316.Ero?lu HE. "Toxic nuclear effects of the organophosphorus insecticide Dichlorvos (DDVP) in human peripheral blood lymphocytes." Acta Biologica Hungarica 60.4(2009):409-16. |
| Description | Cases of sensitization to dichlorvos have been seen inchrysanthem growers, horticulturists, technicians andin a chemist. |
| Description | Dichlorvos is an organophosphate insecticide and inhibitor of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE; IC50s = 269 and 44 nM, respectively). It also binds to the M2 muscarinic receptor in rat heart homogenates. Dichlorvos is lethal to 4-week old German cockroach (B. germanica) nymphs (LD50 = 0.108 μg per insect) and silkworms (B. mori) in third instar (LC50 = 6.63 mg/L) after 24 hours. It is lethal to zebrafish (D. rerio) embryos (LC50 = 39.75 mg/L after 24 hours) and decreases swimming activity of larvae 6 days after fertilization when administered at a concentration of 25 mg/L in tank water. Dichlorvos (150 ppm for 80 weeks) also increases the incidence of benign and malignant neoplasms in male rats from 47 to 88% as compared to controls. |
| Chemical Properties | Dichlorvos is available as an oily colourless to amber liquid with an aromatic chemical odour. It is slightly soluble in water but soluble in kerosene, ethanol, chloroform, and acetone and miscible with alcohol, aromatic and chlorinated hydrocarbon solvents, aerosol propellants, and other non-polar solvents. Dichlorvos in contact with strong acids or alkalis undergoes decomposition and releases hazardous products toxic gases and vapours such as phosphorus, chlorinated oxides, and carbon monoxide. |
| Chemical Properties | Dichlorvos occurs as an oily colorless to amber liquid with slight solubility in water. It hasan aromatic chemical odor. Dichlorvos is used as an agricultural insecticide for the controlof crop pests, such as fl ies, aphids, spider mites, caterpillars, and thrips, and also pests instore grains, and parasitic worms in animals, in fl ea collars for dogs. Occupational workersand the general public can be exposed to dichlorvos while working with the manufacture,formulation, and application on agricultural crops, and when used as a fumigant, and aspest strips. Human exposures also occur through food contamination. |
| Chemical Properties | Dichlorvos is a colorless to amber liquid witha mild aromatic odor. |
| Physical properties | Colorless to yellow liquid with a mild aromatic odor |
| Uses | Dichlorvos is used for the control of household and public healthinsect pests and the control of sucking and chewing pests in a wide rangeof crops. It is used as a veterinary anthelmintic, as an ectoparasiticide onfish and domestic pets and a vapour phase domestic insecticide as well forthe control of phorid and sciarid flies in mushroom compost. |
| Uses | Organophosphorus insecticide and fumigant used against flies, mosquitoes andmoths. |
| Uses | Cholinesterase inhibitor. Anthelmintic, insecticide. |
| Uses | anesthetic |
| Definition | ChEBI: An alkenyl phosphate that is the 2,2-dichloroethenyl ester of dimethyl phosphate. |
| Brand name | Atgard (Boehringer Ingelheim Animal Health); Equigard (Boehringer Ingelheim Animal Health); Equigel (Boehringer Ingelheim Animal Health); TASK Tabs (Boehringer Ingelheim Animal Health). |
| General Description | An aromatic colorless to amber liquid absorbed in a dry carrier. Denser than water and slightly soluble in water. Toxic by inhalation, skin absorption, absorption, or ingestion. Flash point 175°F or higher. When heated to high temperatures may emit toxic chloride fumes and phosgene gas. Used as a pesticide. |
| Air & Water Reactions | Slightly soluble in water. |
| Reactivity Profile | DICHLORVOS MIXTURE is incompatible with strong acids and bases. Dichlorvos is slowly hydrolyzed in acidic media and rapidly hydrolyzed by alkalis. Dichlorvos is corrosive to iron and mild steel. . Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. |
| Health Hazard | Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. |
| Health Hazard | Exposures to dichlorvos through all routes, namely, oral, dermal, and respiratory,cause adverse effects to species of laboratory animals, such as rats, mice, and rabbits.The symptoms of poisoning include perspiration, nausea, salivation, vomiting, diarrhea,drowsiness, fatigue, headache, and in severe cases, tremors, ataxia, convulsions,and coma. Humans exposed to dichlorvos show many symptoms of poisoning that include, butare not limited to, irritability, confusion, headache, speech diffi culties, sweating, blurredvision, drowsiness or insomnia, numbness, tingling sensations, incoordination, tremor,abdominal cramps, diffi culty in breathing or respiratory depression and slow heart beat,impaired memory concentration, disorientation, and severe depressions. |
| Health Hazard | Highly toxic by all routes of exposure;exhibits acute, delayed, and chronic poison-ing; cholinesterase inhibitor; signs and symp-toms of exposure are similar to those ofother organophosphates; toxic effects includesweating, twitching of muscle, constrictionof pupils, lacrimation, salivation, tightnessin the chest, wheezing, slurred speech, nau-sea, vomiting, abdominal pain, and diarrhea;high exposure can result in coma, cessationof breathing, and death. Oral LD50 valuein rodents reported in the literature varieswidely from 17 to 80 mg/kg in rat and61–275 mg/kg in mouse. LC50 inhalation (mouse): 13 mg/m3 /4 h LD50 skin (mouse): 206 mg/kg LD50 oral (wild bird): 12 mg/kg. |
| Fire Hazard | Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. |
| Agricultural Uses | Insecticide, Acaricide, Nematicide: Dichlorvos is used for insect control in food-storageareas, green-houses, and barns, and control of insectson livestock. It is not generally used on outdoor crops.Dichlorvos is sometimes used for insect control in workplacesand in the home. Dichlorvos used in pest controlis diluted with other chemicals and used as a spray. It canalso be incorporated into plastic that slowly releases thechemical. Veterinarians use it to control parasites on pets.Dichlorvos is effective against mushroom flies, aphids, spidermites, caterpillars, thrips, and white flies in greenhouse,outdoor fruit, and vegetable crops. It is used to treat a varietyof parasitic worm infections in dogs, livestock, and humans.Dichlorvos can be fed to livestock to control botflylarvae in the manure. It acts against insects as both a contactand a stomach poison. It is used as a fumigant and hasbeen used to make pet collars and pest strips. It is availableas an aerosol and soluble concentrate. Not approved for usein EU countries. A U.S. EPA restricted Use Pesticide(RUP). Dichlorvos also exists as a breakdown product. |
| Trade name | ALCO® Dichlorvos; APAVAP®;ASTROBOT®; ATGARD®; BAY 19149®; BAYER 19149®;BENFOS®; BIBESOL®; BREVINYL®; BREVINYLE 50®; CANOGARD®; CEKUSAN®; CYPONA®;DEDEVAP®; DERRIBAN®; DERRIBANTE®; DES®;DEVIKOL®; DICLORCAL 50®; DIDIVANE; DIVIPAN®;DOOM®; DQUIGARD®; DUO-KILL®; DURAVOS®;ELASTREL®; EQUIGARD®[C]; EQUIGEL®[C];ESTROSEL®; ESTROSOL®; FECAMA®; FEKAMA®;FLY-DIE®; FLY FIGHTER®; HERKOL®; INSECTIGASD®; KRECALVIN®; LINDAN®; MAFU®; MARVEX®;MOPARI®; NEFRAFOS®; NERKOL®; NOGOS®; NOPEST®;NOVOTOX®; NUVA®; NUVAN®; OKO®;OMS 14®; PANAPLATE®; PHOSVIT®; PRENTOX®;SD 1750®; SUCHLOR®; SZKLARNIAK®; TAP9VP®; TASK®; TENAC®; TETRAVOS®; UNIFOS(PESTICIDE)®; UNITOX®; VAPONA® et al.[C]; VAPONITE®; VERDICAN®; VERDIPOR®;VERDISOL®; VINYLOFOS®; VINYLOPHOS®;WINYLOPHOS® |
| Contact allergens | Cases of sensitization to this organophosphorus compound with several commercial names (Benfos, Brevinyl, Chlorvinphos, DDVP, Equigard, Fly fghte, Nogos, and Unifos) were occupationally seen in chry-santhem growers, horticulturists, technicians, and in a chemist. |
| Safety Profile | Confirmed carcinogen with carcinogenic and tumorigenic data. Poison by ingestion, inhalation, skin contact, subcutaneous, intravenous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. Human mutation data reported. A cholinesterase inhibitor, it is used in flea (pest) collars for pets. No neurotoxicity has been observed. It is very rapidly metabolized and excreted. When heated to decomposition it emits very toxic fumes of Cl and POx. See also PARATHION. |
| Potential Exposure | A potential danger to those involvedin manufacture, formulation and application of this fumigant insecticide in household, public health and agriculturaluses. Used as an insecticide and as an anthelminthic forswine and dogs. |
| Veterinary Drugs and Treatments | Dichlorvos is effective in swine against Ascaris, Trichuris, Ascaropsstrongylina and Oesophagostomum spp. Dichlorvos as a “No Pest Strip” is used as an ectoparasiticideforsmall mammals. It is also used as a premise spray to keep fly populationscontrolled. In horses, dichlorvos is labeled as beingeffective for the treatmentand control of bots, pinworms, large and small bloodworms,and large roundworms, but no systemic equine products are currentlybeing marketed in the USA. Dichlorvos was available for use internally in dogs and cats forthe treatment of roundworms and hookworms, but no productsare currently being marketed since newer, safer and more effectiveanthelmintics have replaced dichlorvos. |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Speed in removing material from skinis of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If thischemical has been inhaled, remove from exposure, beginrescue breathing (using universal precautions, includingresuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24-48 h following overexposure. |
| Carcinogenicity | Two epidemiological studiesreporting an association between exposure to dichlorvosresin strips and childhood cancer were reviewedby EPA and found to have biases and confounders thatcould explain the observed associations. Additional studiesthat correct for the control of potential biases and problems ofexposure determination are needed before an associationbetween dichlorvos and childhood cancer can be established. |
| Environmental Fate | Biological. When dichlorvos was incubated with sewage sludge for one week at 29°C,it was converted to dichloroethanol, dichloroacetic acid, ethyl dichloroacetate and aninorganic phosphate. In addition, dimethyl phosphate formed in the presence or absenceof microorganisms (Lieberman and Alexander, 1983). Dichlorvos degraded fastest innonsterile soils and decomposed faster in soils that were sterilized by gamma radiationthan in soils that were sterilized by autoclaving. After one day of incubation, the percentof dichlorvos degradation that occurred in autoclaved, irradiated and nonsterile soils were17, 88 and 99, respectively (Getzin and Rosefield, 1968). Soil. In a silt loam and sandy loam, reported Rf values were 0.79 and 0.80, respectively(Sharma et al., 1986). Plant. Metabolites identified in cotton leaves include dimethyl phosphate, phosphoricacid, methyl phosphate and O-demethyl dichlorvos (Bull and Ridgway, 1969). Photolytic. Dichlorvos should not undergo direct photolysis since it does not absorbUV light at wavelengths >240 nm (Gore et al., 1971). Chemical/Physical. Releases very toxic fumes of phosphorus oxides and chlorine whenheated to decomposition (Sax and Lewis, 1987). Slowly hydrolyzes in water and in acidic media but is more rapidly hydrolyzed underalkaline conditions to dimethyl hydrogen phosphate and dichloroacetaldehyde (Capel etal., 1988; Hartley and Kidd, 1987; Worthing and Hance, 1991). In the Rhine River (pH7.4), the hydrolysis half-life of dichlorvos was 6 hours (Capel et al., 1988). Atkinson and Carter (1984) estimated a half-life of 320 days for the reaction ofdichlorvos with ozone in the atmosphere. |
| Metabolic pathway | The metabolism of dichlorvos has been extensively studied particularlyin mammals. Dichlorvos is rapidly transformed in both environmentaland biological situations via a hydrolytic mechanism to yielddimethyl phosphate and dichloroacetaldehyde which is further metabolisedto 2,2-dichloroethanol or dechlorinated to glycolic acid. An additionalimportant route in mammals involves demethylation catalysedby glutathione-S-methyl transferase to yield methylglutathione anddesmethyldichlorvos. |
| storage | Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with dichlorvos you should be trained on its proper handling and storage. Store in tightly closed containers in a cool, wellventilated area away from strong acids; strong alkalis.Dichlorvos will attack some forms of mild iron, plastics,rubber, and coatings. |
| Shipping | UN3018 Organophosphorus pesticides, liquid,toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials |
| Toxicity evaluation | Acute oral LD50 for rats: ca. 50 mg /kg |
| Degradation | Dichlorvos is slowly hydrolysed in water and in acidic media and rapidlyhydrolysed by alkali to dichloroacetaldehyde (2) and dimethyl phosphate(3) (PM) |
| Incompatibilities | Contact with oxidizers may cause therelease of phosphorous oxides. Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such ashydrideds and active metals. Partial oxidation by oxidizingagents may result in the release of toxic phosphorus oxides Corrosive to iron, mild steel, some forms of plastics, rubber, and coatings |
| Toxics Screening Level | The initial threshold screening level (ITSL) for dichlorvos is 0.5 μg/m3 with an annual averaging time (AT). |
| Waste Disposal | 50% hydrolysis is obtainedin pure water in 25 minutes @ 70_x0003_°C and in 61.5 days @20C. A buffered solution yields 50% hydrolysis (37.5°C) in301 minutes at pH 8, 462 minutes at pH 7, 620 minutes atpH 5.4. Hydrolysis yields no toxic residues. Incineration in afurnace equipped with an afterburner and alkaline scrubber isrecommended as is alkaline hydrolysis followed by soilburial. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.Must be disposed properly by following package label directions or by contacting your local or federal environmentalcontrol agency, or by contacting your regional EPA office. |
| References | [1] G A PETROIANU. Weak inhibitors protect cholinesterases from stronger inhibitors (dichlorvos): in vitro effect of tiapride.[J]. International Journal of Toxicology, 2005, 24 2: 79-86. DOI: 10.1080/10915810590921360 [2] CARMEN L.P. SILVEIRA Mohyee E E Amira T Eldefrawi. Putative M2 muscarinic receptors of rat heart have high affinity for organophosphorus anticholinesterases[J]. Toxicology and applied pharmacology, 1990, 103 3: Pages 474-481. DOI: 10.1016/0041-008x(90)90320-t [3] ZHI-YONG ZHANG. Acute toxicity of organophosphorus and pyrethroid insecticides to Bombyx mori.[J]. Journal of Economic Entomology, 2008, 101 2: 360-364. DOI: 10.1603/0022-0493(2008)101[360:atooap]2.0.co;2 [4] SI?MAN T. Dichlorvos-induced developmental toxicity in zebrafish.[J]. Toxicology and Industrial Health, 2010, 26 9: 567-573. DOI: 10.1177/0748233710373089 [5] REUBER M D. Carcinogenicity of dichlorvos.[J]. Clinical Toxicology, 1981, 18 1: 47-84. DOI: 10.3109/15563658108990013 |
Dichlorvos Preparation Products And Raw materials
| Raw materials | Sodium hydroxide-->Methanol-->Sulfuric acid-->Toluene-->Benzene-->Chlorine-->Xylene-->EMULSIFIER-->Chloral-->Trichloroethylene-->White phosphorus-->SULPHOSUCCINIC ACID ESTER-->Trimethyl phosphite-->Trichlorfon-->2-Fluoro-5-iodotoluene |
| Preparation Products | Naled-->CALVINPHOS |
