56-72-4 Usage
Uses
Used in Agricultural Applications:
Coumaphos is used as an insecticide and acaricide for the control of a wide variety of livestock insects, including cattle grubs, screwworms, lice, scabies, flies, and ticks. It is also used against ectoparasites that live on the outside of host animals such as sheep, goats, horses, pigs, and poultry.
Used in Veterinary Medicine:
Coumaphos is used as a veterinary medication to control larvae of Diptera and ticks on cattle. It has also been used to control Varroa mite in honeybees.
Used in Beekeeping:
Coumaphos has applications in beekeeping, where it is used to control Varroa mites, which are harmful parasites of honeybees.
Used in Control of Texas Cattle Fever:
The USDA uses coumaphos in dip vats along the U.S.-Texas border to control ticks that carry Texas Cattle Fever.
Used in Poultry and Cattle Feed:
Coumaphos is added to cattle and poultry feed to control the development of fly larvae that breed in manure.
Air & Water Reactions
Insoluble in water. Coumaphos hydrolyzes slowly under alkaline conditions.
Reactivity Profile
Organothiophosphates, 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.
Hazard
Use may be restricted; cholinesterase
inhibitor. Questionable carcinogen.
Health Hazard
Highly 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/kgLD50 skin (rat): 860 mg/kgLC50 inhalation (rat): ～300 mg/m3.
Health Hazard
Very 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 Hazard
Exposures 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 Hazard
When heated to decomposition, Coumaphos emits very toxic fumes of sulfur oxides, phosphorus oxides, and chlorides. Incompatible with piperonyl butoxide. Stable in water.
Trade name
AGRIDIP?; 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 Profile
Poison 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 Exposure
A 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.
Carcinogenicity
There 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 pathway
By 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.
Metabolism
Degradation 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.
Shipping
UN2783 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 evaluation
The 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.
Degradation
Note 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).
Incompatibilities
Organophosphates 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 Disposal
Coumaphos 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
Check Digit Verification of cas no
The CAS Registry Mumber 56-72-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 56-72:
(4*5)+(3*6)+(2*7)+(1*2)=54
54 % 10 = 4
So 56-72-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3
56-72-4Relevant articles and documents
Analogues with fluorescent leaving groups for screening and selection of enzymes that efficiently hydrolyze organophosphorus nerve agents
Brise?o-Roa, Luis,Hill, Jim,Notman, Stuart,Sellers, David,Smith, Andy P.,Timperley, Christopher M.,Wetherell, Janet,Williams, Nichola H.,Williams, Gareth R.,Fersht, Alan R.,Griffiths, Andrew D.
, p. 246 - 255 (2007/10/03)
Enzymes that efficiently hydrolyze highly toxic organophosphorus nerve agents could potentially be used as medical countermeasures. As sufficiently active enzymes are currently unknown, we synthesized twelve fluorogenic analogues of organophosphorus nerve agents with the 3-chloro-7-oxy-4- methylcoumarin leaving group as probes for high-throughput enzyme screening. This set included analogues of the pesticides paraoxon, parathion, and dimefox, and the nerve agents DFP, tabun, sarin, cyclosarin, soman, VX, and Russian-VX. Data from inhibition of acetylcholinesterase, in vivo toxicity tests of a representative analogue (cyclosarin), and kinetic studies with phosphotriesterase (PTE) from Pseudomonas diminuta, and a mammalian serum paraoxonase (PON1), confirmed that the analogues mimic the parent nerve agents effectively. They are suitable tools for high-throughput screens for the directed evolution of efficient nerve agent organophosphatases.
Compositions against wood-destroying insects
-
, (2008/06/13)
The present invention relates to long-acting compositions against wood-destroying insects, characterized in that they contain a) insecticidally active compounds, b) organic natural compounds or organic synthetic compounds or mixtures thereof as carrier material, c) optionally microbicidally active compounds, d) optionally attractants or development-inhibitory compounds for insects, e) and optionally formulation auxiliaries.
Synthesis of new O,O -dialkyl-O-coumarinophosphorothioates and their pesticidal bioassay against Helicoverpa armigera
Chavan, Vishal P.,Mane, Avinash S.,Shingare, Murlidhar S.
, p. 339 - 341 (2007/10/03)
A series of compounds O,O-dialkyl-O-coumarinophosphorothioates have been synthesized and screened for pesticidal activities against Helicoverpa armigera. Some of the compounds (3,4,6 and 7) show significant activities while rest of the compounds show moderate activities.
Liquid formulations
-
, (2008/06/13)
A pour-on formulation comprising one or more ectoparasiticides in a solvent system comprising 80 to 98% w/v of a fixed oil and 2 to 20% w/v of a volatile silicone, a method for its preparations and its use in the control of ectoparasiticides on animals.
Biocidal macroemulsions containing polyvinyl alcohol
-
, (2008/06/13)
The present invention relates to new macroemulsions which contain 0.001 to 60 percent by weight of at least one active compound from the class comprising the phosphates and/or carbamates, 0 to 50 percent by weight of aromatic diluents, 0.001 to 20 percent by weight of polyvinyl alcohol having a mean molecular weight of between 5,000 and 150,000 and a content of acetate groups of between 2 and 30 mol %, and/or 0.001 to 20 percent by weight of a nonlphenol/propylene oxide/ethylene oxide adduct of the formula STR1 in which X represents integers from 10 to 50 and Y represents integers from 15 to 65, and/or 0.001 to 20 percent by weight of ethylene oxide/propylene oxide/ethylene oxide block copolymers having a mean molecular weight of between 2,000 and 8,000 and HLB values of between 8 and 30, and water and, if appropriate, additives, and in which the oil phase is dispersed in the aqueous phase in the form of droplets having a mean particle diameter of 0.1 to 3.0 μm.
Process for formulating a synthetic drug for use in animal feed, and resulting formulation
-
, (2008/06/13)
A method of formulating a synthetic drug for use in animal feed, for the purpose of reducing carry-over of the synthetic drug to subsequent lots of animal feed in the feed mill.
Method of controlling insects and parasites with an aqueous localized pour-on formulation
-
, (2008/06/13)
An aqueous pour-on formulation for localized external application to animals comprises an aqueous carrier, an effective amount of a water-insoluble anti-parasitic agent suspended or dispersed in the aqueous carrier, and a colored dye to enable the application to be observed. Preferred water-insoluble agents include pyrethroids, organophosphorus compounds, formamidines, thiazoles and avermectins. Use of an aqueous system avoids skin reactions sometimes found when non-aqueous solvent systems are used.
Oil-in-water emulsions, and their use
-
, (2008/06/13)
Novel oil-in-water emulsions, which contain (a) 0.1 to 80% by weight of at least one sparingly water-soluble active compound (as herein defined) selected from agrochemical active compounds, active compounds for combating pests in the domestic field and hygiene field and/or pharmacologically active compounds, (b) 1 to 20% by weight of at least one alkylaryl polyglycol ether of the general formula STR1 wherein R1 represents a hydrogen atom or an alkyl group having 1 to 16 carbon atoms, R3 represents a hydrogen atom or a methyl group, m is 1, 2 or 3, and n is an integer from 10 to 50, if appropriate in a mixture with an alkylarylsulphonic acid salt of the general formula STR2 wherein R3 represents an alkyl group having 8 to 35 carbon atoms and Me≈ represents an alkali metal cation, an equivalent of an alkaline earth metal cation or a cation of the general formula STR3 wherein R', R", R'" and RIV independently of one another represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms, (c) water, (d) if necessary, 1 to 30% by weight of at least one poorly water-miscible organic solvent and/or a solubilizer, and (e) if appropriate 0.05 to 15% by weight of one or more additives, the sum of the components being 100% by weight in each case, a process for the preparation of these emulsions and their use in the field appropriate to the active compound.
