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Coumaphos

Coumaphos Basic information
Product Name:Coumaphos
Synonyms:3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioate;3-chloro-4-methyl-7-coumarinyldiethylphosphorothioate;3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphoric acid ester;3-chloro-4-methyl-7-hydroxycoumarindiethylthiophosphoricacidester;3-Chloro-4-methylumbelliferone o-ester with O,O-diethyl phosphorothioate;3-chloro-4-methylumbelliferoneo-esterwitho,o-diethylphosphorothioate;3-chloro-7-diethoxyphosphinothioyloxy-4-methylcoumarin;3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioate
CAS:56-72-4
MF:C14H16ClO5PS
MW:362.77
EINECS:200-285-3
Product Categories:Insecticide, nematocide.;MELDANE;Agro-Products;Heterocycles;Phosphorylating and Phosphitylating Agents;Sulfur & Selenium Compounds;AcaricidesAlphabetic;C;CO - CZPesticides;Insecticides;Oeko-Tex Standard 100;AcaricidesPesticides&Metabolites;Alpha sort;CAlphabetic;INSECTICIDE;OrganophorousMethod Specific;Pesticides;Pesticides&Metabolites
Mol File:56-72-4.mol
Coumaphos Structure
Coumaphos Chemical Properties
Melting point 95-97oC
Boiling point 449.9±55.0 °C(Predicted)
density 1.4740
vapor pressure 1.3 x 10-5 Pa (20 °C)
Fp 100 °C
storage temp. APPROX 4°C
form solid
Water Solubility 1.5 mg l-1 (20 °C)
Merck 13,2584
BRN 327083
Stability:Stable. Combustible. Incompatible with alkalies, strong oxidising agents.
CAS DataBase Reference56-72-4(CAS DataBase Reference)
NIST Chemistry ReferenceCoumaphos(56-72-4)
EPA Substance Registry SystemCoumaphos (56-72-4)
Safety Information
Hazard Codes T+,N,Xn,F
Risk Statements 21-28-50/53-36-20/21/22-11
Safety Statements 28-36/37-45-60-61-36-26-16
RIDADR 2783
WGK Germany 3
RTECS GN6300000
HazardClass 6.1(a)
PackingGroup II
Hazardous Substances Data56-72-4(Hazardous Substances Data)
ToxicityLD50 in female, male rats (mg/kg): 16, 41 orally (Gaines)
MSDS Information
Coumaphos Usage And Synthesis
DescriptionTechnical coumaphos is a tan crystalline solid with a slight sulphur odour. It is insoluble in water; slightly soluble in acetone, chloroform, and ethanol; and soluble in organic solvents. Coumaphos when heated undergoes decomposition and releases very toxic fumes of sulphur oxides, phosphorous oxides, and chlorides. It is used for the control of a wide variety of livestock insects, including cattle grubs, screwworms, lice, scabies, flies, and ticks. It is used against ectoparasites, which are insects that live on the outside of host animals such as sheep, goats, horses, pigs, and poultry. Coumaphos is incompatible with alkalis, strong oxidising agents, pyrethroids, and piperonyl butoxide. The U.S. EPA has grouped coumaphos as RUP.
Chemical Propertiescoumaphos is a tan crystalline solid with a slight sulfur odor. It is insoluble in water, slightly soluble in acetone, chloroform, and ethanol, and soluble in organic solvents. It is used for the control of a wide variety of livestock insects, including cattle grubs, screwworms, lice, scabies, fl ies, and ticks. It is used against ectoparasites, which are insects that live outside the host animals, such as sheep, goats, horses, pigs, and poultry. Coumaphos is incompatible with pyrethroids and piperonyl butoxide. The US EPA has grouped coumaphos as an RUP. Acute dermal exposures to occupational workers occur during mixing, loading, and application of coumaphos, especially in the livestock dip-vat and hand-held sprayer uses
Chemical PropertiesCoumaphos is a white to brownish crystalline solid with a slight sulfurous odor
Chemical Propertiestan or beige solid
UsesInsecticide, nematocide.
Usesinsecticide, cholinesterase inhibitor
UsesCoumaphos is used to control larvae of Diptera and ticks on cattle. It has also recently been used to control Varroa mite in honeybees.
Brand nameBaymix (Bayer AnimalHealth); Meldane (Bayer Animal Health).
General DescriptionSlightly brownish crystals with a slight sulfurous odor. Used for the control of a wide variety of livestock insects including cattle grubs, lice, scabies, flies, and ticks; the common ectoparasites of sheep, goats, horse, swine, and poultry as well as for screwworms in all these animals.
Air & Water ReactionsInsoluble in water. Coumaphos hydrolyzes slowly under alkaline conditions.
Reactivity ProfileOrganothiophosphates, such as Coumaphos, 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. Coumaphos reacts with strong oxidizing agents and alkaline materials.
HazardUse may be restricted; cholinesterase inhibitor. Questionable carcinogen.
Health HazardHighly toxic compound; choline stearaseinhibitor; toxic symptoms include headache,dizziness, blurred vision, muscle spasm,vomiting, abdominal pain, diarrhea, chestpain, and shortness of breath; high dose maycause seizure, respiratory paralysis, comaand death; ingestion of 15–20 g can be fatalto adult humans.
LD50 oral (rat): 13 mg/kg
LD50 skin (rat): 860 mg/kg
LC50 inhalation (rat): ~300 mg/m3.
Health HazardVery toxic, probable oral lethal dose is 50-500 mg/kg, or between 1 teaspoonful and 1 oz. for a 70 kg (150 lb.) person. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes.
Health HazardExposures to coumaphos cause signs of poisoning such as diarrhea, drooling, diffi culty in breathing, leg and neck stiffness among occupational workers. Acute inhalation of coumaphos causes headaches, dizziness, and incoordination. Moderate poisoning causes muscle twitching and vomiting while severe poisoning leads to fever, toxic psychosis, lung edema, and high blood pressure. Repeated exposures cause irritability, confusion, headache, speech diffi culties, effects on memory concentration, disorientation, severe depressions, sleepwalking, and drowsiness or insomnia among occupational workers. Coumaphos has been classifi ed as non-carcinogenic to humans
Fire HazardWhen heated to decomposition, Coumaphos emits very toxic fumes of sulfur oxides, phosphorus oxides, and chlorides. Incompatible with piperonyl butoxide. Stable in water.
Agricultural UsesInsecticide, Nematocide; Veterinary medication: The U.S. EPA classifies the formulations 11.6% EC and 42% flowable concentrate end-use products as Restricted Use Pesticides (RUPs) because they pose a hazard of acute poisoning from ingestion. Coumaphos is an insecticide/acaricide used to control a wide variety of liver stock insects including cattle grubs, fleeceworms, lice scabies, flies, and ticks; the common ectoparasites of beef cattle, dairy cows, sheep, goats, horse, swine, and poultry as well as for screw worms in all these animals. The USDA uses coumaphos in dip vats along the U.S.-Texas border to control ticks that carry Texas Cattle Fever. It is added to cattle and poultry feed to control the development of fly larvae that breed in manure. It has applications in beekeeping.
Trade nameAGRIDIP®; ASUNTOL®; AZUNTHOL®; BAY® 21/199; BAYER® 21/199; BAYMIX®; BAYMIX® 50; CHECKMITE®; CO-RAL®[C]; DELICE®; MELDANE®; MELDONE®; MUSCATOX®; NEGASHUNT®; DIOLICE®; RESITOX®; SUNTOL®; UMBETHION®
Safety ProfilePoison by ingestion, sktn contact, inhalation, and intraperitoneal routes. Mutation data reported. When heated to decomposition, it emits very toxic fumes of SOx, PO,, and Cl-. See also COUMARIN.
Potential ExposureA potential danger to those involved in the manufacture, formulation, and application of this material which is used for control of a wide variety of livestock insects including cattle grubs, lice scabies, flies, and ticks; the common ectoparasites of sheep, goats, horse, swine, and poultry; as well as for screw worms in all these animals.
CarcinogenicityThere was no evidence of carcinogenicity at any dose in rats fed diets that contained 1, 5, or 25 ppm coumaphos (0.05, 0.25, or 1.22 mg/kg/day (males); 0.07, 0.36, or 1.70 mg/kg/day (females)) for 2 years . There was no evidence of carcinogenicity in another study when rats were given diets that contained 10 or 20 ppm coumaphos for 103 weeks .
Metabolic pathwayBy UV irradiation of coumaphos in solutions, three dimeric products are isolated and identified as the head-to-tail anti-dimer, its oxidation product, and the head-to-tail syn-dimer.
MetabolismDegradation occurs rapidly in the liver of the cow and rat. The principal metabolite excreted in urine is diethyl hydrogen phosphorothioate. Deethylation products are also found in lesser amounts. Photolytic DT50 on soil surface is 23.8 d.
ShippingUN2783 Organo phosphorus pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material. UN3018 Organophosphorus pesticides, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Toxicity evaluationThe acute oral LD50 values for male and female rats are 41 and 16 mg/kg, respectively. Inhalation LC50 values (1 h) for male and female rats are >1081 and 341 mg/m3 air. In 2-yr trials, rats tolerated 100 mg/kg diet.
DegradationNote that technical coumaphos may contain the dechlorinated analogue 'Potasan' (O-4-methyl-2-oxo-2H-chromen-7-yl O,O-diethyl phosphorothioate) (2) as an impurity (Waleski, 1966; Volpk and Mallet, 1976).
Coumaphos is stable to hydrolysis in aqueous media although the pyrone ring opens in dilute alkali and re-closes on acidification (PM). In water at pH 4.0, 5.5, 6.3, 7.0 and 8.5, the DT50 values were 33, 67, 124, 347 and 29 days, respectively. Coumaphos degraded first to coroxon (coumaphos oxon) (3), presumably by an oxidative mechanism and this was hydrolysed to chlorferon (3-chloro-4-methyl-7-hydroxycoumarin)(4). The analysis was by TLC (Mallet and Volpe,1978).
IncompatibilitiesOrganophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrideds and active metals. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Keep away from piperonyl butoxide, oxidizers, strong bases, water, and heat
Waste DisposalCoumaphos can be decomposed by heating with concentrated alkali. Large amounts should be incinerated in a unit equipped with effluent gas scrubbing. Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (>=100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration with effluent gas scrubbing is recommended. 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 environmental control agency, or by contacting your regional EPA office
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