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Coumachlor

PubChem CID
54682651
Structure
Coumachlor_small.png
Coumachlor_3D_Structure.png
Molecular Formula
Synonyms
  • COUMACHLOR
  • 81-82-3
  • Tomorin
  • Cumachlor
  • Ratilan
Molecular Weight
342.8 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2011-12-26
  • Modify:
    2024-12-28
Description
Coumachlor is a hydroxycoumarin.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Coumachlor.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxychromen-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C19H15ClO4/c1-11(21)10-15(12-6-8-13(20)9-7-12)17-18(22)14-4-2-3-5-16(14)24-19(17)23/h2-9,15,22H,10H2,1H3
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

DEKWZWCFHUABHE-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC(=O)CC(C1=CC=C(C=C1)Cl)C2=C(C3=CC=CC=C3OC2=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.11.20)

2.2 Molecular Formula

C19H15ClO4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Nikkaji Number

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-1-benzopyran-2-one
  • 3-(alpha-acetonyl-p-chlorobenzyl)-4-hydroxycoumarin
  • coumachlor

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
342.8 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
3.3
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
342.0658866 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
342.0658866 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
63.6Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
533
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Colorless solid; [HSDB]

3.2.2 Color / Form

Colorless, crystalline solid
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA23 (1993) 215
Crystals
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 447

3.2.3 Melting Point

169-171 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 447

3.2.4 Solubility

Soluble in alcohol, acetone, chloroform. Slightly soluble in Benzene, ether
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 447
In water, 5 mg/l @ 20 °C.
Shiu WY et al; Rev Environ Contam Toxicol 116: 15-187 (1990)

3.3 Chemical Classes

3.3.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.3.2 Pesticides

Rodenticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Rodenticides, Anticoagulant

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 4
View All
NIST Number
239470
Library
Main library
Total Peaks
226
m/z Top Peak
299
m/z 2nd Highest
301
m/z 3rd Highest
342
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
52562
Library
Replicate library
Total Peaks
128
m/z Top Peak
299
m/z 2nd Highest
43
m/z 3rd Highest
121
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 15
View All
Authors
Beck B, Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
Instrument
Q Exactive Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
12.4 min
Precursor m/z
343.0732
Precursor Adduct
[M+H]+
Top 5 Peaks

163.039 999

343.0733 862

285.0313 240

181.0414 98

325.063 7

Thumbnail
Thumbnail
License
CC BY
2 of 15
View All
Authors
Beck B, Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
Instrument
Q Exactive Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30 (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
12.4 min
Precursor m/z
343.0732
Precursor Adduct
[M+H]+
Top 5 Peaks

163.039 999

285.0313 862

181.0414 127

189.0546 18

343.0733 7

Thumbnail
Thumbnail
License
CC BY

4.2 IR Spectra

4.2.1 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
189219
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3 Raman Spectra

Catalog Number
189219
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Pesticide active substances -> Rodenticides

7.2 EU Pesticides Data

Active Substance
coumachlor
Status
Not approved [Reg. (EC) No 1107/2009]
Legislation
2004/129/EC

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Anticoagulants
Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)
Rodenticides
Substances used to destroy or inhibit the action of rats, mice, or other rodents. (See all compounds classified as Rodenticides.)

8.2 Mechanism of Action

Both 4-hydroxycoumarin derivatives and indandiones (also known as oral anticoagulants) are antagonists of vitamin K. Their use as rodenticides is based on the inhibition of the vitamin K-dependent step in the synthesis of a number of blood coagulation factors. The vitamin K-dependent proteins involved in the coagulation cascade (Fig. 1) are the procoagulant factors II (prothrombin), VII (proconvertin), IX (Christmas factor) and X (Stuart-Prower factor), and the coagulation-inhibiting proteins C and S. All these proteins are synthesized in the liver. Before they are released into the circulation the various precursor proteins undergo substantial (intracellular) post-translational modification. Vitamin K functions as a co-enzyme in one of these modifications, namely the carboxylation at well-defined positions of 10-12 glutamate residues into gamma-carboxyglutamate (Gla). The presence of these Gla residues is essential for the procoagulant activity of the various coagulations factors. Vitamin K hydroquinone (KH2) is the active co-enzyme, and its oxidation to vitamin K 2,3-epoxide (KO) provides the energy required for the carboxylation reaction. The epoxide is than recycled in two reduction steps mediated by the enzyme KO reductase (Fig. 2). The latter enzyme is the target enzyme for coumarin anticoagulants. Their blocking of the KO reductase leads to a rapid exhaustion of the supply of KH2, and thus to an effective prevention of the formation of Gla residues. This leads to an accumulation of non-carboxylated coagulation factor precursors in the liver. In some cases these precursors are processed further without being carboxylated, and (depending on the species) may appear in the circulation. At that stage the under-carboxylated proteins are designated as descarboxy coagulation factors. Normal coagulation factors circulate in the form of zymogens, which can only participate in the coagulation cascade after being activated by limited proteolytic degradation. Descarboxy coagulation factors have no procoagulant activity (i.e. they cannot be activated) and neither they can be converted into the active zymogens by vitamin K action. Whereas in anticoagulated humans high levels of circulating descarboxy coagulation factors are detectable, these levels are negligible in warfarin-treated rats and mice. /Anticoagulant rodenticides/
WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.46 (1995)
Similar to warfarin, with delayed actions on prothrombin level and blood clotting, resulting in death by hemorrhage.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 447

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Used as anticoagulant rodenticide (structural analog of warfarin); [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Restricted Notes
No longer registered as a pesticide for use in the US; [HSDB]
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
Rodenticide.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 447
For coumachlor (USEPA/OPP Pesticide Code: 224200) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Coumachlor (81-82-3). Available from, as of February 26, 2003: https://npirspublic.ceris.purdue.edu/ppis/

9.2 Methods of Manufacturing

Preparation: F. Litvan, W. Stoll, US 2648682 (1953 to J. R. Geigy).
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 447
Coumachlor is made by the condensation of 3-carbethoxy-4-hydroxycoumarin and p-chlorobenzalacetone.
Sittig, M. (ed.) Pesticide Manufacturing and Toxic Materials Control Encyclopedia. Park Ridge, NJ: Noyes Data Corporation. 1980., p. 211

9.3 Formulations / Preparations

Trade Names: Tomorin, Ratilan, G 23133.
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Coumachlor (81-82-3). Available from, as of February 26, 2003: https://npirspublic.ceris.purdue.edu/ppis/

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 4
View All
Pictogram(s)
Health Hazard
Signal
Warning
GHS Hazard Statements

H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H412 (100%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P273, P319, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

STOT RE 2 (100%)

Aquatic Chronic 3 (100%)

Specific target organ toxicity (repeated exposure) - category 2

Hazardous to the aquatic environment (chronic) - category 3

10.1.3 Hazards Summary

A vitamin K antagonist; In human poisoning cases after ingestion, causes disruption of clotting factors (lower doses) and hemorrhages (higher doses); [HSDB] First generation anticoagulant rodenticide; Discontinued by Ciba-Geigy in 1984; [INCHEM] See Warfarin.

10.2 Accidental Release Measures

10.2.1 Disposal Methods

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

10.3 Transport Information

10.3.1 Shipping Name / Number DOT/UN/NA/IMO

UN 3024; Coumarin derivative pesticides, liquid, flammable, toxic, NOS, flashpoint less than 23 °C
UN 3025; Coumarin derivative pesticides, liquid, toxic, flammable, NOS, flashpoint 23 °C or more
UN 3026; Coumarin derivative pesticides, liquid, toxic, NOS
UN 3027; Coumarin derivative pesticides, solid, toxic, NOS
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for COUMACHLOR (6 total), please visit the HSDB record page.

10.3.2 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 22, 2002: https://www.ecfr.gov
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
International Air Transport Association. Dangerous Goods Regulations 44th ed. 2003. International Air Transport Association, Montreal, Canada., p. 167
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
IMDG; International Maritime Dangerous Goods Code; International Maritime Organization p.3270, 6219-21 (1998)

10.4 Regulatory Information

Status Regulation (EC)
2004/129/EC

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

11.1.2 Interactions

The following drugs ... may increase ... response to coumarin or indandione derivatives: alcohol (acute intoxication), allopurinol, aminosalicylic acid, amiodarone, anabolic steroids, chloral hydrate, chloramphenicol, cimetidine, clofibrate, co-trimoxazole, danazol, dextrothyroxine sodium, diazoxide, diflunisal, disulfiram, erythromycin, ethacrynic acid, fenoprofen calcium, glucagon, ibuprofen, indomethacin, influenza virus vaccine, isoniazid, meclofenamate, mefenamic acid, methylthiouracil, metronidazole, miconazole, nalidixic acid, neomycin (oral), pentoxifylline, phenylbutazone, propoxyphene, propylthiouracil, quinidine, quinine, salicylates, streptokinase, sulfinpyrazone, sulfonamides, sulindac, tetracyclines, thiazides, thyroid drugs, tricyclic antidepressants, urokinase, vitamin E. /Coumarin & indandione derivatives/
American Hospital Formulary Service-Drug Information 88. Bethesda, MD: American Society of Hospital Pharmacists, 1988 (Plus supplements)., p. 731
The following drugs ... may ... decrease ... response to coumarin or indandione derivatives: alcohol (chronic alcoholism), barbiturates, carbamazepine, corticosteroids, corticotropin, ethchlorvynol, glutethimide, griseofulvin, mercaptopurine, methaqualone, oral contraceptives containing estrogen, rifampin, spironolactone, vitamin K. /Coumarin & indandione derivatives/
American Hospital Formulary Service-Drug Information 88. Bethesda, MD: American Society of Hospital Pharmacists, 1988 (Plus supplements)., p. 732

11.1.3 Antidote and Emergency Treatment

Human exposure to second-generation and indandione anticoagulants produces symptoms consistent with anticoagulation effects (e.g., hematomas, hematemesis, hematuria, easy bruisability). Treatment of cases of exposure, particularly of substantial and repeated exposure, may require vitamin K1 therapy and monitoring of prothrombin times for periods of many months.
WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.67 (1995)
Vitamin K1. ... For suicidal ingestions with large amounts taken, if there is uncertainty about the amount of bait ingested or the general health of the patient, phytonadione (vitamin K1) given orally protects against the anticoagulant effect of these rodenticides, with essentially no risk to the patient. In accidental ingestions with healthy children involving only a taste or single swallow, no medical treatment is required, but children should be observed for bleeding and bruising. If a larger amount may have been ingested, prothrombin time (PT) should be monitored at 24 and 48 hours, with phytonadione therapy initiated for elevated PT or clinical signs of bleeding. CAUTION: Phytonadione, specificaly, is required. Neither vitamin K3 (menadione, Hykinone) nor vitamin K4 (menadiol) is an antidote for these anticoagulants. /Coumarins and Indandiones/
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 171
Gastrointestinal decontamination. If large amounts of anticoagulant have been ingested within several hours prior to treatment, consider gastric decontamination procedures ... . /Coumarins and Indandiones/
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 171
Determine prothrombin time. If anticoagulant has been ingested any time in the preceding 15 days, determination of the prothrombin time (PT) provides a basis for judging the severity of poisoning. Patients who ingest large amounts, particularly of the superwarfarin compounds, will likely have a very prolonged period of decreased prothrombin activity. Patients may need to be treated for as long as 3 or 4 months. If the PT is significantly lengthened, give Aquamephyton intramuscularly. ... /Coumarins and Indandiones/
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 171
Caution: Adverse reactions, some fatal, have occurred from intravenous phytonadione injections, even when recommended dosage limits and injection rates were observed. For this reason, the intravenous route should be used only in cases of severe poisoning. Flushing, dizziness, hypotension, dyspnea, and cyanosis have characterized adverse reactions. Antidotal therapy in cases of severe bleeding should be supplemented with transfusion of fresh blood or plasma. Use of fresh blood or plasma represents the most rapidly effective method of stopping hemorrhage due to these anticoagulants, but the effect may not endure. Therefore, the transfusions should be given along with phytonadione therapy. Determine prothrombin time (PT) and hemoglobin concentrations every 6-12 hours to assess effectiveness of antihemorrhagic measures. When normal blood coagulation is restored, it may be advisable to drain large hemotomata. Ferrous sulfate therapy may be appropriate in the recuperative period to rebuild lost erythrocyte mass. /Coumarins and Indandiones/
U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 172

11.1.4 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ Typical features of poisoning result from increased bleeding tendency and include: minor poisoning: coagulation disturbance detected only by laboratory analyses; moderate poisoning: coagulation disturbance resulting in hematomata, hematuria, blood in feces or excessive bleeding from minor cuts or abrasions, gum bleeding; severe poisoning: retroperitoneal hemorrhage, severe GI bleeding, cerebrovascular accidents, massive hemorrhage (internal bleeding) resulting in shock. If anaemia or liver disease is present then the above features may be more severe and persistent and the poisoning may be more difficult to control. The onset of the signs of poisoning may not be evident until a few days after ingestion. /Anticoagulant rodenticides/
WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.68 (1995)

11.1.5 Non-Human Toxicity Values

LD50 Rat (albino Norway) oral 900.0 mg/kg
WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.53 (1995)

11.1.6 Populations at Special Risk

SRP: Persons with bleeding disorders or who are taking anticoagulants should be protected from exposure.

11.2 Ecological Information

11.2.1 Ecotoxicity Excerpts

/BIRDS and MAMMALS/ Min lethal dose in dog, swine (mg/kg): <5, <5 orally.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 447
/AQUATIC SPECIES/ An experimental study was carried out on the toxic effects of technical coumachlor and Tomorin (coumachlor 1%) on the fresh water fish Gambusia affinis. The results are compared with the effects caused by technical warfarin on the same species. The toxicity of these substances follows a decreasing order: Tomorin, coumachlor and warfarin. Symptoms were similar for all 3, hemorrhages and cutaneous lesions being predominant features when coumarin concentration in the water medium was low, neurological and asphyxia symptoms appearing when concentration was high.
Fernandez Bernaldo de Quiros C; Bol R Soc Esp Hist Nat Secc Biol 76 (1-2): 109-122 (1978)
/ACCIDENTAL POISONINGS/ /In domestic animals,/ signs of poisoning occur after a latent period of 12 hr to several days and may include: bruising easily with occasional nose or gum bleeds; blood in stools or urine; excessive bleeding from minor cuts or abrasions; laboured breathing; pale mouth and cold gums; anorexia and general weakness. A reliable indication of an anticoagulant effect is the determination of prothrombin time. /Anticoagulant rodenticides/
WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.65 (1995)

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Wiley References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 KEGG: Pesticides

16.4 ChemIDplus

16.5 UN GHS Classification

16.6 NORMAN Suspect List Exchange Classification

16.7 EPA DSSTox Classification

16.8 EPA Substance Registry Services Tree

16.9 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Hazardous Substances Data Bank (HSDB)
  7. ChEBI
  8. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  9. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  10. EU Pesticides Database
  11. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  12. Hazardous Chemical Information System (HCIS), Safe Work Australia
  13. NITE-CMC
    coumachlor (ISO); 3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxycoumarin - FY2008 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/08-mhlw-0011e.html
  14. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
    coumachlor (ISO); 3-[1-(4-chlorophenyl)-3-oxobutyl]-4-hydroxycoumarin
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  15. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  16. Japan Chemical Substance Dictionary (Nikkaji)
  17. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  18. MassBank Europe
  19. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  20. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  21. SpectraBase
  22. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  23. Springer Nature
  24. Wikidata
  25. Wikipedia
  26. Wiley
  27. PubChem
  28. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  29. GHS Classification (UNECE)
  30. EPA Substance Registry Services
  31. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  32. PATENTSCOPE (WIPO)
CONTENTS