COUMAPHOS

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H16ClO5PS
Molecular Weight	362.766
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOP(=S)(OCC)OC1=CC2=C(C=C1)C(C)=C(Cl)C(=O)O2

InChI

InChIKey=BXNANOICGRISHX-UHFFFAOYSA-N

InChI=1S/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

HIDE SMILES / InChI

Molecular Formula	C14H16ClO5PS
Molecular Weight	362.766
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.iasj.net/iasj?func=fulltext&aId=56885 | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=558.185

Coumaphos is an organophosphate insecticide used against ectoparasites. It was approved by FDA for the control of gastrointestinal roundworms in cattle (Purina brand name). It was also used in medicated feed against internal parasites (Ascaidia galli, Capilleria obsignata and Heterakis gallinarum) in layer chickens (Meldane brand name). However, coumaphos is highly toxic to birds. Sever acute toxicity and eventual death were caused in hens after they were given oral doses of 10mg/kg for 1-8 days.The oral LD50 for coumaphos is 3mg/kg in wildbirds, 29.4mg/kg in mallard ducks, 7.94mg/kg in pheasants and 14mg/kg in chicken. Due to its toxicity, coumaphos is no longer available as a drug.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Worm infection 4 Sources: https://www.gpo.gov/fdsys/pkg/CFR-1996-title21-vol6/pdf/CFR-1996-title21-vol6-sec558-185.pdf	Curative		Approved 8583	PURINA Approved Use Control of gastrointestinal roundworms (Haemonchus spp., Ostertagia spp., Cooperia spp., Nematodirus spp., Trichostrongylus spp.).

PubMed

Title	Date	PubMed
Miticide residues in Virginia honeys.	2009-12	19565169
Pesticide use and adult-onset asthma among male farmers in the Agricultural Health Study.	2009-12	19541724
Molecular survey of pyrethroid resistance mechanisms in Mexican field populations of Rhipicephalus (Boophilus) microplus.	2009-10	19565267
Combined use of GC-TOF MS and UHPLC-(Q)TOF MS to investigate the presence of nontarget pollutants and their metabolites in a case of honeybee poisoning.	2009-05-27	19382786
Longitudinal trends in organophosphate incidents reported to the National Pesticide Information Center, 1995-2007.	2009-04-20	19379510
Synergistic interactions between in-hive miticides in Apis mellifera.	2009-04	19449624
Cancer incidence among pesticide applicators exposed to permethrin in the Agricultural Health Study.	2009-04	19440497
First detection of Varroa destructor resistance to coumaphos in Argentina.	2009-04	19009360
Biodegradation of chlorpyrifos by lactic acid bacteria during kimchi fermentation.	2009-03-11	19199784
An immobilized ortho-palladated dimethylbenzylamine complex as an efficient catalyst for the methanolysis of phosphorothionate pesticides.	2009-02-02	19105733
Transient expression of organophosphorus hydrolase to enhance the degrading activity of tomato fruit on coumaphos.	2009-02	19235273
Biodegradation of coumaphos, chlorferon, and diethylthiophosphate using bacteria immobilized in Ca-alginate gel beads.	2009-02	18845433
Effect of rainfall exposure immediately after a single dip treatment with coumaphos on the control of Rhipicephalus (Boophilus) microplus (Acari: Ixodidae) on infested cattle.	2009-01	19198522
Depression and pesticide exposures among private pesticide applicators enrolled in the Agricultural Health Study.	2008-12	19079725
Microarray analysis of acaricide-inducible gene expression in the southern cattle tick, Rhipicephalus (Boophilus) microplus.	2008-12	18834453
New multiresidue method using solid-phase extraction and gas chromatography-micro-electron-capture detection for pesticide residues analysis in royal jelly.	2008-10-31	18804771
Bee honey as an environmental bioindicator of pesticides' occurrence in six agricultural areas of Greece.	2008-10	18231699
Beta-cyclodextrins as carriers of monoterpenes into the hemolymph of the honey bee (Apis mellifera) for integrated pest management.	2008-09-24	18710247
Differential response to diazinon and coumaphos in a strain of Boophilus microplus (Acari: Ixodidae) collected in Mexico.	2008-09	18826034
Survival of honey bee (Hymenoptera: Apidae) spermatozoa incubated at room temperature from drones exposed to miticides.	2008-08	18767713
Multi-residue analysis of traces of pesticides and antibiotics in honey by HPLC-MS-MS.	2008-06	18425645
Incident diabetes and pesticide exposure among licensed pesticide applicators: Agricultural Health Study, 1993-2003.	2008-05-15	18343878
Dietary intake and its contribution to longitudinal organophosphorus pesticide exposure in urban/suburban children.	2008-04	18414640
Better than eating worms? Children's dietary exposure to OP pesticides.	2008-04	18414618
Residue distribution of the acaricide coumaphos in honey following application of a new slow-release formulation.	2008-02	18069655
Pesticides and atopic and nonatopic asthma among farm women in the Agricultural Health Study.	2008-01-01	17932376
Pesticide residues in beeswax samples collected from honey bee colonies (Apis mellifera L.) in France.	2007-11	17879980
Global comparative analysis of ESTs from the southern cattle tick, Rhipicephalus (Boophilus) microplus.	2007-10-12	17935616
Characterization of permethrin-resistant Boophilus microplus (Acari: Ixodidae) collected from the state of Coahuila, Mexico.	2007-09	17915523
Acaricide rotation strategy for managing resistance in the tick Rhipicephalus (Boophilus) microplus (Acarina: Ixodidae): laboratory experiment with a field strain from Costa Rica.	2007-09	17915514
[Control of Rhipicephalus sanguineus (Latrielle, 1806) (Acari: Ixodidae) in the kennel of the UFMG Veterinary School, Belo Horizonte, Minas Gerais, Brazil].	2007-08-13	18554440
Pesticide urinary metabolite levels of children in eastern North Carolina farmworker households.	2007-08	17687456
Biodegradation of chlorferon and diethylthiophosphate by consortia enriched from waste cattle dip solution.	2007-07	16987656
What's killing American honey bees?	2007-06	17564497
Critical evaluation of the modified-adult immersion test with discriminating dose bioassay for Boophilus microplus using American and Australian isolates.	2007-05-31	17433549
[Determination of organic phosphorus pesticide residues in scallion by gas chromatography coupled with microwave clean-up].	2007-05	17679438
Effect of UV radiation and temperature on mineralization and volatilization of coumaphos in water.	2007-05	17474015
Effect of coumaphos on cholinesterase activity, hematology, and biochemical blood parameters of bovines in tropical regions of Mexico.	2007-05	17474014
Gene silencing of the tick protective antigens, Bm86, Bm91 and subolesin, in the one-host tick Boophilus microplus by RNA interference.	2007-05	17196597
Gas chromatography mass spectrometry determination of acaricides from honey after a new fast ultrasonic-based solid phase micro-extraction sample treatment.	2007-03-30	19071541
First report of permethrin-resistant Boophilus microplus (Acari: Ixodidae) collected within the United States.	2007-03	17427702
Therapeutic and persistent efficacy of spinosad applied as a pour-on or a topical spray against natural infestations of chewing and sucking lice on cattle.	2007-02-28	17027158
Serial analysis of gene expression in the southern cattle tick following acaricide treatment of larvae from organophosphate resistant and susceptible strains.	2007-02	17257208
Determination of synthetic acaricides residues in beeswax by high-performance liquid chromatography with photodiode array detector.	2007-01-02	17386431
Phorate exposure and incidence of cancer in the agricultural health study.	2006-08	16882526
[Resolution of synchronous fluorimetric spectrum for carbaryl and coumaphos and its application study].	2006-06	16961238
A survey of pesticide residues in pollen loads collected by honey bees in France.	2006-04	16686121
Organic diets significantly lower children's dietary exposure to organophosphorus pesticides.	2006-02	16451864
Analysis of organophosphorus pesticides in whole milk by solid phase microextraction gas chromatography method.	2006	16753956
Acute poisoning from food contaminated by coumaphos.	2006	16538949

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose is 27.2 and 36,3 grams per ton of feed (0.003 and 0.004 percent) for laying chickens and replacement pullets, respectively. In cattles, coumaphos is given at a dose of 0.0002 pound (0.091 gram) per 100 pounds of body weight per day.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:15 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:15 GMT 2025`
Record UNII	L08SZ5Z5JC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COUMAPHOS

Common Name

English

COUMAFOS

Preferred Name

English

O-3-CHLORO-4-METHYL-7-COUMARINYL O,O-DIETHYL PHOSPHOROTHIOATE

Systematic Name

English

COUMAFOS [MART.]

Common Name

English

BAYER-21199

Code

English

O-(3-CHLORO-4-METHYL-2-OXO-2H-1-BENZOPYRAN-7-YL) O,O-DIETHYL PHOSPHOROTHIOATE

Systematic Name

English

O-3-CHLORO-4-METHYL-2-OXO-2H-CHROMEN-7-YL O,O-DIETHYL PHOSPHOROTHIOATE

Systematic Name

English

NSC-8944

Code

English

COUMAPHOS [ISO]

Common Name

English

COUMAPHOS [GREEN BOOK]

Common Name

English

coumafos [INN]

Common Name

English

COUMAPHOS [HSDB]

Common Name

English

COUMAPHOS [MI]

Common Name

English

BAYER 21199

Code

English

Classification Tree Code System Code

WHO-VATC

QP53AF08