An official website of the United States government

Coumatetralyl

PubChem CID
54678504
Structure
Coumatetralyl_small.png
Coumatetralyl_3D_Structure.png
Molecular Formula
Synonyms
  • COUMATETRALYL
  • 5836-29-3
  • Racumin
  • Endrocid
  • Endrocide
Molecular Weight
292.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2011-12-26
  • Modify:
    2024-12-28
Description
Yellowish-white crystalline powder; colorless when pure; odorless. This material is used as a rodenticide, functioning as an anticoagulant that does not induce bait-shyness. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
Coumatetralyl is a hydroxycoumarin.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Coumatetralyl.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-yl)chromen-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C19H16O3/c20-18-15-9-3-4-11-16(15)22-19(21)17(18)14-10-5-7-12-6-1-2-8-13(12)14/h1-4,6,8-9,11,14,20H,5,7,10H2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ULSLJYXHZDTLQK-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1CC(C2=CC=CC=C2C1)C3=C(C4=CC=CC=C4OC3=O)O
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C19H16O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

5836-29-3

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 UN Number

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • coumateralyl
  • coumatetralyl

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
292.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
292.109944368 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
292.109944368 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
46.5Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
481
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
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

Yellowish-white crystalline powder; colorless when pure; odorless. This material is used as a rodenticide, functioning as an anticoagulant that does not induce bait-shyness. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
Yellowish-white odorless solid; Colorless when pure; [CAMEO] Colorless powder; [MSDSonline]

3.2.2 Color / Form

Colorless crystals
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)

3.2.3 Odor

ODORLESS
Martin, H. and C.R. Worthing (eds.). Pesticide Manual. 4th ed. Worcestershire, England: British Crop Protection Council, 1974., p. 130

3.2.4 Taste

TASTELESS
Martin, H. and C.R. Worthing (eds.). Pesticide Manual. 4th ed. Worcestershire, England: British Crop Protection Council, 1974., p. 130

3.2.5 Melting Point

349 °F (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
172-176 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
Yellowish crystals. MP: 166-172 °C /Technical/
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)

3.2.6 Solubility

In water, 425 mg/L at 20 °C and pH 7
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
Soluble in alcohols and acetone; slightly soluble in benzene, toluene, and diethyl ether.
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
SOL IN DIL ALKALI & MOST ORG SOLVENTS
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 137
Practically insoluble in benzene, moderately soluble in alcohols, and readily soluble acetone and dioxane. The sodium salt is fully soluble in water.
Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 1291
For more Solubility (Complete) data for COUMATETRALYL (6 total), please visit the HSDB record page.

3.2.7 Vapor Pressure

8.5X10-6 mPa /6.38X10-11 mm Hg/ at 20 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)

3.2.8 LogP

log Kow = 3.46
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)

3.2.9 Stability / Shelf Life

Thermally stable up to at least 150 °C. Not hydrolysed by water over 5 days (25 °C).
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 234

3.2.10 Decomposition

When heated to decomposition it emit acird smoke and fumes.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1571
... DT50 >1 yr (pH 4-9). Rapidly decomposed in aq soln exposed to sunlight or u.v. light; DT50 about 1 hr.
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 234

3.2.11 Dissociation Constants

pKa = 4.5 to 5.0
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)

3.2.12 Other Experimental Properties

ENOLIC FORM OF COMPD HAS ACIDIC PROPERTIES AND CAN FORM SALTS WITH METALS
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 137

3.3 Chemical Classes

3.3.1 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
291854
Library
Main library
Total Peaks
207
m/z Top Peak
292
m/z 2nd Highest
121
m/z 3rd Highest
188
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
120582
Library
Replicate library
Total Peaks
40
m/z Top Peak
292
m/z 2nd Highest
121
m/z 3rd Highest
188
Thumbnail
Thumbnail

4.1.2 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

141.071 100

143.0502 30.75

106.0424 28.68

93.0346 22.63

135.0452 22.15

Thumbnail
Thumbnail
2 of 6
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

141.071 100

291.1027 72.88

247.1128 41.46

106.0424 32.97

135.0452 22.93

Thumbnail
Thumbnail

4.1.3 LC-MS

1 of 40
View All
Authors
B. Beck [dtc,com], J. Hollender [dtc]
Instrument
Exploris 240 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
10.203 min
Precursor m/z
293.1172
Precursor Adduct
[M+H]+
Top 5 Peaks
293.1171 999
Thumbnail
Thumbnail
License
CC BY-SA
2 of 40
View All
Authors
B. Beck [dtc,com], J. Hollender [dtc]
Instrument
Exploris 240 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
10.203 min
Precursor m/z
293.1172
Precursor Adduct
[M+H]+
Top 5 Peaks

293.1173 999

175.039 267

91.0543 58

131.0856 49

163.0389 39

Thumbnail
Thumbnail
License
CC BY-SA

4.2 IR Spectra

4.2.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich
Lot Number
BCCJ5797
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3 Other Spectra

Intense mass spectral peaks: 91 m/z, 121 m/z, 130 m/z, 188 m/z, 292 m/z
Pfleger, K., H. Maurer and A. Weber. Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Parts I and II. Mass Spectra Indexes. Weinheim, Federal Republic of Germany. 1985., p. 508

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Pesticide active substances -> Rodenticides

7.2 EU Pesticides Data

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

8 Pharmacology and Biochemistry

8.1 Biological Half-Life

Eight groups of mice dosed orally with a different anticoagulant rodenticide in a /single oral/ dose equal to one-half the lethal dose 50 (LD(50)), were killed at various times up to 21 days after administration. The eight anticoagulant rodenticides /brodifacoum, bromadiolone, chlorophacinone, coumatetralyl, difenacoum, difethialone, flocoumafen and warfarin/ were assayed in plasma and liver by an LC-ESI-MS/MS method. Depending on the compound, the limit of quantification was set at 1 or 5 ng/mL in plasma. In liver, the limit of quantification was set at 250 ng/g for coumatetralyl and warfarin and at 100 ng/g for the other compounds. The elimination half-lives in plasma for first-generation rodenticides were shorter than those for second-generation rodenticides. Coumatetralyl, a first-generation product, had a plasma elimination half-life of 0.52 days. ... The elimination half-lives in liver varied from 15.8 days for coumatetralyl to 307.4 days for brodifacoum.
Vandenbroucke V et al; J Vet Pharmacol Ther. 2008 Oct;31(5):437-45 (2008)

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Used as anticoagulant rodenticide; Not currently produced or used in the US; [HSDB]
Restricted Notes
Not registered as a pesticide for use in the US; [HSDB]
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
For coumatetralyl (USEPA/OPP Pesticide Code: 496100) 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./PEER REVIEWED**
Anticoagulant rodenticide... . Does not induce bait shyness.
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
Rodenticide
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 347
Effective rat killers, odorless and flavorless, they cause spontaneous hemorrhages in the rodent which ingests them, causing death from hypoxia. They are effective against brown, and black rats, mouse, field mouse, field vole, and hamster. ...They are also used in pulverized form or as fumigants for moles. /Coumarin derivatives/
International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 560
In holes and runs and as a powder for mixing with baits.
Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 1291

9.1.1 Use Classification

Hazard Classes and Categories ->

9.1.2 Household Products

California Safe Cosmetics Program (CSCP)

Cosmetics product ingredient: Coumatetralyl (ISO) (4- hydroxy-3-(1,2,3,4-tetrahydro-1-naphthyl) coumarin)

Reason for Listing: Classified by the European Union as a reproductive toxicant Category 1B in Annex VI to Regulation (EC) 1272/2008

Potential Health Impacts: Reproductive Toxicity

Product count: 1

9.2 Methods of Manufacturing

Coumatetralyl is produced by the condensation of 4-hydroxycoumarin and 1,2,3,4-tetrahydro-1-naphthol.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed. Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present,p. V31 435 (2003)

9.3 Formulations / Preparations

'RACUMIN 57' (7.5 G AI/KG), USED AS TRACKING POWDER OR AS A BAIT CONCENTRATE (1 PART 'RACUMIN 57' + 19 PARTS BAIT MATERIAL); READY-PREPARED BAITS (375 MG/KG).
Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987., p. 193
Liquid, bait concentrate, ready-made bait, powder.
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 347
Formulators' Trade Names: Couma Wax, Super Couma Rat (Chema Industries); Cumakil (Zapi Industrie Chimiche S.p.A); Ratryl (VAPCO); Wopro-coumatetralyl (Simonis).
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 347
Bay 25634
U.S. Department of Health and Human Services, Public Health Service, Center for Disease Control, National Institute for Occupational Safety Health. Registry of Toxic Effects of Chemical Substances (RTECS). National Library of Medicine's current MEDLARS file., p. 85/8309
For more Formulations/Preparations (Complete) data for COUMATETRALYL (6 total), please visit the HSDB record page.

9.4 General Manufacturing Information

The WHO Recommended Classification of Pesticides by Hazard identifies coumatetralyl (technical grade) as Class IB: highly hazardous; Main Use: rodenticide.
WHO International Programme on Chemical Safety; The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2009 p.21 (2010)
First introduced in 1956, coumatetralyl is one of the most widely used first-generation anticoagulants. It is not, however, available in the United States.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed. Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present,p. V31 435 (2003)
USA: Not registered.
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 347

10 Identification

10.1 Analytic Laboratory Methods

Analysis is by UV spectroscopy, particulars from Bayer AG.
Worthing, C.R. and S.B. Walker (eds.). The Pesticide Manual - A World Compendium. 8th ed. Thornton Heath, UK: The British Crop Protection Council, 1987., p. 193
Methods for handling residue analysis of pesticides such as coumatetralyl by TLC with fluorometric detection are discussed.
MALLET VN; QUANTITATIVE THIN-LAYER CHROMATOGRAPHY OF PESTICIDES BY IN SITU FLUOROMETRY; ACS SYMP SER 136 (CHO8): 127-57 (1980)
A method for determination of racumin rodenticide in soil and water by high performance liquid chromatography.
Mollhoff E; Pflanzenschutz-Nachrichten Bayer 36 (1): 54-62 (1983)
Residues of warfarin, coumatetralyl, difenacoum, brodifacoum, bromadiolone, diphacinone, and chlorophacinone in animal tissues were extracted with CHCl3-MeCO. Extracts were cleaned-up by an integrated gel permeation and adsorption chromatography procedure which divided the rodenticides into 2 groups. Residues were then determined and confirmed using normal-phase, ion-pair and weak ion-exchange HPLC techniques. Ion-pair gradient separation resolved all 7 rodenticides in a single chromatographic analysis. UV detection methods were employed for all 7 rodenticides. Use of a diode array detection system permitted additional confirmation of residues down to 0.1 mg/kg by matching UV spectra and derivations of spectra. Sensitive fluorescence detection was possible for the coumarin-based rodenticides, but not for diphacinone and chlorophacinone. Post-column pH-switching fluorescence detection methods were superior to other methods of fluorescence detection of coumarin-based rodenticides. Recoveries from spiked liver tissue were around 90% at levels from 0.05 to 1 mg/kg. Detection limits of around 0.002 mg/kg for most rodenticides and of 0.01 mg/kg for warfarin could be achieved with animal tissue extracts.
Hunter K; High-performance liquid chromatographic strategies for the determination and confirmation of anticoagulant rodenticide residues in animal tissues; J Chromatogr 321(2): 255-72 (1985)

10.2 Clinical Laboratory Methods

A method is described for detection of coumarin anticoagulants in biological fluids by gas liquid chromatography-mass spectrometry.
VON MEYER L ET AL; THE DETECTION OF COUMARIN ANTICOAGULANTS IN BIOLOGICAL FLUIDS BY GAS LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; FORENSIC TOXICOL, PROC EUR MEET INT ASSOC FORENSIC TOXICOL: 245-51 (1980)
Analyte: Coumatetralyl; Matrix: Animal tissues; Procedure: HPLC/FD; Detection Level: 2 ug/kg. /from table/
WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.43 (1995)
Analyte: Coumatetralyl; Matrix: Serum; Procedure: HPLC; Detection Level: 10 ug/l. /from table/
WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.43 (1995)
This paper presents a fully validated method for the qualitative identification of bromadiolone, brodifacoum, coumachlor, coumatetralyl, difenacoum and warfarin in whole blood specimens. Samples are protein precipitated with acetonitrile, processed via solid-phase extraction and analyzed by high-performance liquid chromatography with high resolution tandem mass spectrometric detection. Limits of detection were 10 ng/mL or better for all analytes.
Schaff JE, Montgomery MA; J Anal Toxicol 37 (6): 321-5 (2013)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 3
View All
Pictogram(s)
Acute Toxic
Health Hazard
Signal
Danger
GHS Hazard Statements

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

H310 (97.7%): Fatal in contact with skin [Danger Acute toxicity, dermal]

H372 (100%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

H412 (97.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P319, P321, P330, P361+P364, P405, 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 43 reports by companies from 4 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.

11.1.2 Hazard Classes and Categories

Acute Tox. 2 (100%)

Acute Tox. 2 (97.7%)

STOT RE 1 (100%)

Aquatic Chronic 3 (97.7%)

Reproductive toxicity - category 1B

Acute toxicity - category 2

Acute toxicity - category 2

Acute toxicity - category 3

Specific target organ toxicity (repeated exposure) - category 1

Hazardous to the aquatic environment (chronic) - category 1

11.1.3 Health Hazards

Overdosage with anticoagulants may cause acute bleeding. Pre-existing blood clotting disease or liver disease may be aggravated by exposure. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

11.1.4 Fire Hazards

(Non-Specific -- Coumarin Derivative Pesticide, Solid, n.o.s.) This material may burn but does not ignite readily. Fire and runoff from fire control water may produce irritating or poisonous gases. Runoff from fire control water may give off poisonous gases. Container may explode in heat of fire. Enolic form of compound has acidic properties and can form salts with metals. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

11.1.5 Hazards Summary

A vitamin K antagonist--causes clotting factor disruption and bleeding; Absorbed through skin; [HSDB] First generation anticoagulant rodenticide; [INCHEM] Registered for use in the EU; Not irritating to skin or eyes of rabbits; Not sensitizing to skin of guinea pigs; No evidence of mutagenic effects; No evidence of teratogenicity in rats or rabbits (although all anti-vitamin K rodenticides classified by this commission May cause harm to the unborn child based on the known human developmental toxicity of Warfarin); The commercial product Racumin® Paste showed potential for skin sensitization in a Magnusson and Kligman study; [eChemPortal: ESIS] See Warfarin.

11.1.6 Fire Potential

Not flammable or combustible.
Sigma-Aldrich; Material Safety Data Sheet for Coumatetralyl, Product Number: 45404, Version 4.3 (Revision Date 12/19/2012). Available from, as of September 27, 2013: https://www.sigmaaldrich.com/catalog/product/fluka/45404?lang=en&region=US

11.2 First Aid Measures

11.2.1 First Aid

Signs and Symptoms of Coumatetralyl Exposure: Coumatetralyl is an anticoagulant. Hemorrhage is the most common sign and may be manifested by hemorrhagic skin rashes and lip, nose, and upper airway bleeding. Upper airway pain, difficulty in speaking and swallowing, and dyspnea (shortness of breath) may occur. Vomiting, abdominal pain, and bloody stools are common. Back pain may be noted.

Emergency Life-Support Procedures: Acute exposure to coumatetralyl exposure may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination.

Inhalation Exposure:

1. Move victims to fresh air. Emergency personnel should avoid self-exposure to coumatetralyl.

2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.

3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

4. RUSH to a health care facility.

Dermal/Eye Exposure:

1. Remove victims from exposure. Emergency personnel should avoid self-exposure to coumatetralyl.

2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.

3. Remove contaminated clothing as soon as possible.

4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes.

5. Wash exposed skin areas THOROUGHLY with soap and water.

6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

7. RUSH to a health care facility.

Ingestion Exposure:

1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.

2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures.

3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of coumatetralyl is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step

4. Ipecac should not be administered to children under 6 months of age.Warning: Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step

4.The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal.

4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water.

5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3- 1/2 oz) is recommended for adults.

6. RUSH to a health care facility. (EPA, 1998)

U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

11.3 Fire Fighting

(Non-Specific -- Coumarin Derivative Pesticide, Solid, n.o.s.) Stay upwind; keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

(Non-Specific -- Coumarin Derivative Pesticide, Solid, n.o.s.) Small fires: dry chemical, carbon dioxide, water spray or foam. Large fires: water spray, fog or foam. (EPA, 1998)

U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

11.3.1 Fire Fighting Procedures

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.
Sigma-Aldrich; Material Safety Data Sheet for Coumatetralyl, Product Number: 45404, Version 4.3 (Revision Date 12/19/2012). Available from, as of September 27, 2013: https://www.sigmaaldrich.com/catalog/product/fluka/45404?lang=en&region=US

11.4 Accidental Release Measures

11.4.1 Isolation and Evacuation

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

11.4.2 Cleanup Methods

Personal precautions: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Sigma-Aldrich; Material Safety Data Sheet for Coumatetralyl, Product Number: 45404, Version 4.3 (Revision Date 12/19/2012). Available from, as of September 27, 2013: https://www.sigmaaldrich.com/catalog/product/fluka/45404?lang=en&region=US

11.4.3 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Incineration: 1) Stuff a package with paper or flammable materials. Burn in the furnace. 2) Dissolve in a combustible solvent. Burn in the furnace by spraying the soln.
United Nations. Treatment and Disposal Methods for Waste Chemicals (IRPTC File). Data Profile Series No. 5. Geneva, Switzerland: United Nations Environmental Programme, Dec. 1985., p. 146

11.4.4 Preventive Measures

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.
Sigma-Aldrich; Material Safety Data Sheet for Coumatetralyl, Product Number: 45404, Version 4.3 (Revision Date 12/19/2012). Available from, as of September 27, 2013: https://www.sigmaaldrich.com/catalog/product/fluka/45404?lang=en&region=US
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.
Sigma-Aldrich; Material Safety Data Sheet for Coumatetralyl, Product Number: 45404, Version 4.3 (Revision Date 12/19/2012). Available from, as of September 27, 2013: https://www.sigmaaldrich.com/catalog/product/fluka/45404?lang=en&region=US

11.5 Handling and Storage

11.5.1 Nonfire Spill Response

(Non-Specific -- Coumarin Derivative Pesticide, Solid, n.o.s.) Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Remove and isolate contaminated clothing at the site. Do not touch spilled material. Use water spray to reduce vapors. With clean shovel place material into clean, dry container and cover. Dike far ahead of large spills for later disposal. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

11.5.2 Storage Conditions

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.
Sigma-Aldrich; Material Safety Data Sheet for Coumatetralyl, Product Number: 45404, Version 4.3 (Revision Date 12/19/2012). Available from, as of September 27, 2013: https://www.sigmaaldrich.com/catalog/product/fluka/45404?lang=en&region=US

11.6 Exposure Control and Personal Protection

11.6.1 Personal Protective Equipment (PPE)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.
Personal protective equipment: Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Hand protection: Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. Full contact Material: Nitrile rubber (minimum layer thickness: 0.11 mm, break through time: 480 min). Splash protection: Material: Nitrile rubber (minimum layer thickness: 0.11 mm Break through time: 480 min). ... Eye protection: Face shield and safety glasses: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin and body protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Sigma-Aldrich; Material Safety Data Sheet for Coumatetralyl, Product Number: 45404, Version 4.3 (Revision Date 12/19/2012). Available from, as of September 27, 2013: https://www.sigmaaldrich.com/catalog/product/fluka/45404?lang=en&region=US

11.7 Stability and Reactivity

11.7.1 Air and Water Reactions

No rapid reaction with air. No rapid reaction with water.

11.7.2 Reactive Group

Alcohols and Polyols

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

11.7.3 Reactivity Profile

Ketones, such as COUMATETRALYL, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

11.8 Transport Information

11.8.1 DOT Emergency Guidelines

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Coumarin derivative pesticide, liquid, flammable, poisonous; Coumarin derivative pesticide, liquid, flammable, toxic; Coumarin derivative pesticide, liquid, poisonous, flammable; Coumarin derivative pesticide, liquid, toxic, flammable/
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Coumarin derivative pesticide, liquid, flammable, poisonous; Coumarin derivative pesticide, liquid, flammable, toxic; Coumarin derivative pesticide, liquid, poisonous, flammable; Coumarin derivative pesticide, liquid, toxic, flammable/
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Coumarin derivative pesticide, liquid, flammable, poisonous; Coumarin derivative pesticide, liquid, flammable, toxic; Coumarin derivative pesticide, liquid, poisonous, flammable; Coumarin derivative pesticide, liquid, toxic, flammable/
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Coumarin derivative pesticide, liquid, flammable, poisonous; Coumarin derivative pesticide, liquid, flammable, toxic; Coumarin derivative pesticide, liquid, poisonous, flammable; Coumarin derivative pesticide, liquid, toxic, flammable/
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
For more DOT Emergency Guidelines (Complete) data for COUMATETRALYL (16 total), please visit the HSDB record page.

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

UN 3024; Coumarin derivative pesticides, liquid, flammable, toxic, flashpoint less than 23 °C
UN 3025; Coumarin derivative pesticides, liquid, toxic, flammable, flashpoint not less than 23 °C
UN 3026; Coumarin derivative pesticides, liquid, toxic
UN 3027; Coumarin derivative pesticides, solid, toxic
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for COUMATETRALYL (6 total), please visit the HSDB record page.

11.8.3 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 (USDOT); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of November 18, 2013: 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. 47th Edition. Montreal, Quebec Canada. 2006., p. 170
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.
International Maritime Organization. IMDG Code. International Maritime Dangerous Goods Code Volume 2 2006, p. 149

11.8.4 DOT Label

Poison

11.9 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Reproductive Toxicity

Authoritative List - EC Annex VI CMRs - Cat. 1B

Report - if used as a fragrance or flavor ingredient

Status Regulation (EC)
2004/129/EC
New Zealand EPA Inventory of Chemical Status
Coumatetralyl: HSNO Approval: HSR002777 Approved with controls

11.9.1 CERCLA Reportable Quantities

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Coumatetralyl is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .
40 CFR 355 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of November 15, 2013: https://www.ecfr.gov

11.10 Other Safety Information

Chemical Assessment

IMAP assessments - 2H-1-Benzopyran-2-one, 4-hydroxy-3-(1,2,3,4-tetrahydro-1-naphthalenyl)-: Environment tier I assessment

IMAP assessments - 2H-1-Benzopyran-2-one, 4-hydroxy-3-(1,2,3,4-tetrahydro-1-naphthalenyl)-: Human health tier I assessment

11.10.1 Toxic Combustion Products

Hazardous decomposition products formed under fire conditions. - Carbon oxides
Sigma-Aldrich; Material Safety Data Sheet for Coumatetralyl, Product Number: 45404, Version 4.3 (Revision Date 12/19/2012). Available from, as of September 27, 2013: https://www.sigmaaldrich.com/catalog/product/fluka/45404?lang=en&region=US

12 Toxicity

12.1 Toxicological Information

12.1.1 Acute Effects

12.1.2 Toxicity Data

LC50 (rat) = 39 mg/m3/4h

12.1.3 Interactions

Resistance to 4-hydroxycoumarin anticoagulant rodenticides has been a problem in some local foci for a number of years. One method of managing resistance could be to use synergists in conjunction with anticoagulants. /The researchers/ investigated the effect of administering cholecalciferol and coumatetralyl alone and in a synergistic mixture to anticoagulant-resistant rats by monitoring plasma factor X concentrations. The study showed that the efficacy of the compounds was significantly improved when they were used together. This synergistic effect led to an increased mortality in female rats that had been treated with both compounds compared to both a control group and groups of rats that had received the compounds singly. An unexpected result from this work was that cholecalciferol when given on its own to rats caused a decrease in plasma factor X concentration. /The researchers/ hypothesize that this effect was due to a vitamin D-induced increase in production of vitamin K-dependent proteins leading to a saturation of the carboxylation process and hence to a significant number of factor X molecules being under-carboxylated and therefore dysfunctional. It is suggested that the reduction in factor X levels is a major component of the increased efficacy of the anticoagulant/calciferol mixture and also that effects on other vitamin K-dependent proteins, e.g. matrix GLA protein, may play a role in the increased mortality seen in female rats.
Kerins GM et al; Comparative Clinical Pathology 11 (1): 59-64 (2002)
Coumatetralyl was admin orally to produce fatal hemorrhage in 32 adult dogs. Dogs used as control group received only lactose. Treated dogs were divided into 4 groups & medicated with vitamin K: group 1, 3 mg/kg first day, 1 mg/kg/day for 5 days; group 2, 3 mg/kg first day only; group 3, 1 mg/kg/day for 6 days; group 4, as control only saline 0.3 ml/kg/day. Mortality rate was 12.5%, 25.0%, 62.5%, and 100%, respectively.
Masaoka T et al; Azabu Daigaku Juigakubu Kenkyu Hokoku 2 (1): 109-17 (1981)

12.1.4 Antidote and Emergency Treatment

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
For more Antidote and Emergency Treatment (Complete) data for COUMATETRALYL (10 total), please visit the HSDB record page.

12.1.5 Human Toxicity Excerpts

/CASE REPORTS/ A healthy man in his 40s presented with a 1-month history of haemoptysis and was unexpectedly found to have an elevated international normalised ratio (INR). He denied any known exposures to anticoagulants. Testing for the possible aetiologies of a high INR revealed coumarin poisoning with coumatetralyl as the cause. The approach to an elevated INR and management and diagnosis of suspected coumarin poisoning is reviewed.
Kay A et al; BMJ Case Rep. 2011 Apr 13;2011

12.1.6 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Lactating female albino rats have been treated with coumatetralyl rodenticide. The lethal effect on mothers was of 40% (using a maximum concentration of toxic substance) while it was of 54% in offsprings.
Marchini S, et al; Parassitologia 20(1-3): p 59-70 (1978)
/LABORATORY ANIMALS: Acute Exposure/ A case study in which pigs were poisoned by coumatetralyl was examined. A total of 18 piglets were first noticed to have pale skin at 2 weeks of age, and 5 died within the next 2 weeks. Another 14 pigs about 10 weeks old turned pale; some were lame and hemorrhaged from the nose and eyes. Eventually 10 of these pigs died. One of the mothers also showed these symptoms but eventually recovered without treatment. Postmortems of three pigs showed severe hemorrhage and edema with hematomas in the lumbar region and hemorrhage into the pleural cavity of one animal. Over an 8 week period, approximately 2 kilograms of the 0.8 percent coumatetralyl commercial powder had been spread along ledges both in the feeding mixing shed and in the two pens containing affected pigs. Experimental pigs were given 0.10, 0.25, 0.50, or 1.00 milligram (mg) coumatetralyl per kilogram (kg) body weight and observed to see if symptoms were similar to those observed in poisoned pigs. Vitamin-K1 therapy was used and its effectiveness as an antidote was evaluated. Lameness was noted in pigs between 3 and 6 days after starting treatment, and the main source of external hemorrhage was from the hole punched for the eartag; this was seen soon after lameness. Difficulty in rising or paralysis often preceded death. Predominant postmortem findings in pigs which died were subcutaneous and interstitial hemorrhages, with edema of the skeletal musculature. The heart, lungs, liver, spleen, kidneys, and skeletal musculature showed no evidence of hemorrhage. A single dose of 1.5 to 2.5 mg/kg vitamin-K1 was effective in curing pigs.
Dobson KJ; Australian Veterinary Journal 49(2): p 98-100 (1973)
/LABORATORY ANIMALS: Acute Exposure/ Cmpd acts as an anticoagulant and causes internal hemorrhages. /rats, oral/
Spencer, E. Y. Guide to the Chemicals Used in Crop Protection. 7th ed. Publication 1093. Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1982., p. 137
/LABORATORY ANIMALS: Acute Exposure/ In warfarin-resistant rats coumatetralyl (0.5 mg/100 g, ip) blocked prothrombin formation and almost completely blocked reformation of vitamin K1 from its epoxide; warfarin had no effect at the same dose level.
Bell RG et al; Biochem Pharmacol 25 (9): 1067-70 (1976)
For more Non-Human Toxicity Excerpts (Complete) data for COUMATETRALYL (12 total), please visit the HSDB record page.

12.1.7 Non-Human Toxicity Values

LD50 Rat oral 16.5 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1570
LD50 Rat dermal 40 mg/kg
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 347
LD50 Mouse oral >1,000 mg/kg
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 235
LD50 Rabbit oral >500 mg/kg
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 235
For more Non-Human Toxicity Values (Complete) data for COUMATETRALYL (6 total), please visit the HSDB record page.

12.2 Ecological Information

12.2.1 Ecotoxicity Values

LC50; Species: Guppy; Concentration: about 1,000 mg/L for 96 hr /Conditions of bioassay not specified/
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 235
LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout); Concentration: 48 mg/L for 96 hr /Conditions of bioassay not specified/
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 235
LC50; Species: Golden orfe; Concentration: 67 mg/L for 96 hr /Conditions of bioassay not specified/
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 235
LD50; Species: Japanese quail oral >2,000 mg/kg bw /Conditions of bioassay not specified/
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 235
LC50; Species: Hen oral >50 mg/kg/day for 8 days
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 235

12.2.2 Environmental Fate / Exposure Summary

Although not currently used in the US, coumatetralyl's production and use as a rodenticide may have result in its direct release to the environment. If released to air, a vapor pressure of 6.38X10-11 mm Hg at 25 °C indicates coumatetralyl will exist solely in the particulate phase in the atmosphere. Particulate-phase coumatetralyl will be removed from the atmosphere by wet or dry deposition. Coumatetralyl contains chromophores that absorb at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, coumatetralyl is expected to have slight mobility based upon an estimated Koc of 3900. The pKa of coumatetralyl is 4.75, indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization of the neural form from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 5.8X10-14 atm-cu m/mole. Volatilization of the anion form from moist soil is not expected because anions do not volatilize. Coumatetralyl is not expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, coumatetralyl is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant and pKa. An estimated BCF of 285 suggests the potential for bioconcentration in aquatic organisms is high. Hydrolysis is not expected to be an important environmental fate process based on experimental data. Coumatetralyl was rapidly decomposed in aqueous solutions which were exposed to sunlight or UV with a half-life of about 1 hour, suggesting a potential for direct photolysis. Occupational exposure and general population exposure should be low or non-existent since coumatetralyl is no longer produced or used in the US. (SRC)

12.2.3 Natural Pollution Sources

Coumarin and its derivatives are synthesized by plants in nearly all families(1). /Coumarin/
(1) Kupidlowska E et al; Annals Botany 73: 525-30 (1994). Available from, as of Apr 11, 2014: https://aob.oxfordjournals.org/content/73/5/525.full.pdf

12.2.4 Artificial Pollution Sources

Although not currently used in the US(1), coumatetralyl's production and use as a rodenticide(2) may have result in its direct release to the environment(SRC).
(1) Farm Chemicals Handbook 2002. Meister Publishing Co., p. C-117 (2002)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)

12.2.5 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3900(SRC), determined from a structure estimation method(2), indicates that coumatetralyl is expected to have slight mobility in soil(SRC). The pKa of coumatetralyl is 4.75(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of coumatetralyl from moist soil surfaces of the neutral form is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-14 atm-cu m/mole(SRC), based upon its vapor pressure, 6.38X10-11 mm Hg(3), and water solubility, 425 mg/L(3). Volatilization from moist soil of the anion form is not expected because anions do not volatilize(SRC). Coumatetralyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not available(SRC, 2013).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Nov 14, 2013: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3900(SRC), determined from a structure estimation method(2), indicates that coumatetralyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral form from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.8X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 6.38X10-11 mm Hg(4), and water solubility, 425 mg/L(4). A pKa of 4.75(4) indicates coumatetralyl will exist partially in the anion form at pH values of 5 to 9 and, therefore, volatilization of the ion form from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(5), an estimated BCF of 285(SRC), from its log Kow of 3.46(4) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Coumatetralyl is not expected to undergo hydrolysis in the environment based on a 5 day experiment(4). Coumatetralyl was rapidly decomposed in aqueous solutions which were exposed to sunlight or UV with a half-life of about 1 hour(4). Biodegradation data in water were not available(SRC, 2013).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Nov 14, 2013: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 15-1 to 15-29 (1990)
(4) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), coumatetralyl, which has a vapor pressure of 6.38X10-11 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase coumatetralyl may be removed from the air by wet or dry deposition(SRC). Coumatetralyl contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

12.2.6 Environmental Abiotic Degradation

Coumatetralyl contains chromophores that absorb at wavelengths >290 nm(1) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Coumatetralyl was not hydrolyzed by water after 5 days at 25 °C(2). The compound was rapidly decomposed in aqueous solutions which were exposed to sunlight or UV with a half-life of about 1 hour(2).
(1) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)

12.2.7 Environmental Bioconcentration

An estimated BCF of 285 was calculated in fish for coumatetralyl(SRC), using a log Kow of 3.46(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). [
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Nov 14, 2013: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

12.2.8 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of coumatetralyl can be estimated to be 3900(SRC). According to a classification scheme(2), this estimated Koc value suggests that coumatetralyl is expected to have slight mobility in soil. The pKa of coumatetralyl is 4.75(3), indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Nov 14, 2014: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)

12.2.9 Volatilization from Water / Soil

A pKa of 4.75(1) indicates coumatetralyl will exist partially in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces of the ionized form is not expected to be an important fate process(SRC). The Henry's Law constant for coumatetralyl is estimated as 5.8X10-14 atm-cu m/mole(SRC) derived from its vapor pressure, 6.38X10-11 mm Hg(1), and water solubility, 425 mg/L(1). This Henry's Law constant indicates that neutral coumatetralyl is expected to be essentially nonvolatile from water and moist soil surfaces(2). Coumatetralyl's is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Coumatetryl (5836-29-3) (2008-2010)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)

12.2.10 Plant Concentrations

Plants containing coumarin(1). /Coumarin/
Genus species
Dipteryx odorata
Common name
Tonka bean
Part
Seed
Concn (ppm)
35,000
Genus species
Galium odoratum
Common name
Woodruff
Part
Plant
Concn (ppm)
13,000
Genus species
Myroxylon balsamum
Common name
Peru balsum
Part
Seed
Concn (ppm)
4,000
Genus species
Zizyphus jujuba
Common name
Ta-Tsao
Part
Leaf
Concn (ppm)
3,000
Genus species
Melitus officinalis
Common name
Yellow sweetclover
Part
Plant
Concn (ppm)
2,000
Genus species
Lavandula angustifola
Common name
English lavender
Part
Plant
Concn (ppm)
1,500
Genus species
Lycopus europeus
Common name
European bugle
Part
Plant
Concn (ppm)
1,200
Genus species
Zea mays
Common name
Corn
Part
Leaf
Concn (ppm)
2,000
Genus species
Ageratum conzyoides
Common name
Mexican ageratum
Part
Shoot
Concn (ppm)
0-1,040
Genus species
Peumus boldus
Common name
Boldo
Part
Leaf
Concn (ppm)
125
Genus species
Tecoma stans
Common name
Yellow elder
Part
Bark
Concn (ppm)
80
Genus species
Eupatorium triplinerve
Common name
Trilinerved eupatorium
Part
Plant
Concn (ppm)
0-150
Genus species
Lavandula latifolia
Common name
Spike lavender
Part
Plant
Concn (ppm)
22
Genus species
Mentha x piperita subsp nothosubsp piperita
Common name
Peppermint
Part
Leaf
Genus species
Acacia farnesiana
Common name
Sweet acacia
Part
Flower
Genus species
Ageratum conyzoides
Common name
Mexican ageratum
Part
Plant
Genus species
Aloe vera
Common name
Aloe
Part
Plant
Genus species
Ammi visnaga
Common name
Visnaga
Part
Plant
Genus species
Apium graveolens
Common name
Celery
Part
Plant
Genus species
Artemisia annua
Common name
Sweet wormwood
Part
Plant
Genus species
Artemisia cappilaris
Common name
Capillary wormwood
Part
Plant
Genus species
Artemisia dracunculus
Common name
Tarragon
Part
Plant
Genus species
Capparis spinosa
Common name
Caper
Part
Plant
Genus species
Cinnamomum aromaticum
Common name
Chinese cinnamon
Part
Bark
Genus species
Cinnamomum verum
Common name
Cinnamon
Part
Bark
Genus species
Citrus aurantium
Common name
Bitter orange
Part
Fruit
Genus species
Daucus carota
Common name
Carrot
Part
Root
Genus species
Ferula alliacea
Common name
Garlic ferula
Part
Plant
Genus species
Filipendula ulmaria
Common name
Meadowsweet
Part
Plant
Genus species
Hordeum vulgare
Common name
Barley
Part
Plant
Genus species
Hyoscyamus niger
Common name
Henbane
Part
Plant
Genus species
Justicia pectoralis
Common name
Curia
Part
Plant
Genus species
Lavandula x intermedia
Common name
Dutch lavender
Part
Plant
Genus species
Levisticum officinale
Common name
Lovage
Part
Root
Genus species
Petiveria alliacea
Common name
Mucura
Part
Root
Genus species
Phoenix dactylifera
Common name
Date palm
Part
Leaf
Genus species
Prunus cerasus
Common name
Sour cherry
Part
Plant
Genus species
Psoralea corylifolia
Common name
Malaya tea
Part
Seed
Genus species
Theobroma caco
Common name
Caco
Part
Seed
Genus species
Trifolium pratense
Common name
Red clover
Part
Flower
Genus species
Trigonella foenum-graesum
Common name
Greek clover
Part
Plant
Genus species
Verbascum thaspus
Common name
Flannelleaf
Part
Leaf
Genus species
Vitis vinifera
Common name
European grape
Part
Fruit
(1) Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical. Coumarin. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of Apr 11, 2014: https://www.ars-grin.gov/duke/
Coumarin and its derivatives are synthesized by plants in nearly all families(1). /Coumarin/
(1) Kupidlowska E et al; Annals Botany 73: 525-30 (1994). Available from, as of Apr 11, 2014: https://aob.oxfordjournals.org/content/73/5/525.full.pdf

12.2.11 Animal Concentrations

Coumatetralyl was not detected (detection limit <0.08 ug/g) in the liver of 11 common buzzards, 4 kestrel falcon, 5 tawny owl, 15 mallard, 13 black coot, or 1 common moorhen; but was detected in 1 of 10 barn-owl at 0.64 ug/g(1). The raptors and water birds were collected in 2003 from Loire Atlantique, France(1). Coumatetralyl was not detected (detection limit <0.02 mg/kg) in the livers of 20 Eurasian otters (Lutra lutra) from the upper Loire River catchment, France(2). Coumatetralyl was detected in 6 of 40 stoats (Mustela erminea) at 0.0046-0.0097 mg/kg and in 3 of 10 weasels (Mustela nivalis) at 0.0085-0.06 mg/kg; animals were collected from central and eastern England from Aug 1996 to Mar 1997(3).
(1) Lambert O et al; Bull Environ Contam Toxicol 79: 91-4 (2007)
(2) Lemarchand C et al; Chemosphere 80: 1120-4 (2010)
(3) McDonald RA et al; Environ Pollut 103: 17-23 (1998)

12.2.12 Probable Routes of Human Exposure

Occupational exposure and general population exposure should be low or non-existent since coumatetralyl is no longer produced or used in the US. (SRC)

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 KEGG: Pesticides

17.4 ChemIDplus

17.5 CAMEO Chemicals

17.6 UN GHS Classification

17.7 NORMAN Suspect List Exchange Classification

17.8 EPA DSSTox Classification

17.9 EPA Substance Registry Services Tree

17.10 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    2H-1-Benzopyran-2-one, 4-hydroxy-3-(1,2,3,4-tetrahydro-1-naphthalenyl)-
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. 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/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
  7. 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
  8. Hazardous Substances Data Bank (HSDB)
  9. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  10. NJDOH RTK Hazardous Substance List
  11. California Safe Cosmetics Program (CSCP) Product Database
    Coumatetralyl (ISO) (4- hydroxy-3-(1,2,3,4-tetrahydro-1-naphthyl) coumarin)
    https://cscpsearch.cdph.ca.gov/search/detailresult/1909
  12. EU Pesticides Database
  13. 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
  14. ChEBI
  15. 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
  16. 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
  17. Hazardous Chemical Information System (HCIS), Safe Work Australia
  18. 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
    coumatetralyl (ISO); 4-hydroxy-3-(1,2,3,4-tetrahydro-1-naphthyl)coumarin
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  19. 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
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. 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
  22. MassBank Europe
  23. 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
  24. 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
    2H-1-Benzopyran-2-one, 4-hydroxy-3-(1,2,3,4-tetrahydro-1-naphthalenyl)-
    http://www.nist.gov/srd/nist1a.cfm
  25. SpectraBase
  26. Springer Nature
  27. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  28. Wikidata
  29. Wikipedia
  30. PubChem
  31. 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
  32. GHS Classification (UNECE)
  33. 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/
  34. EPA Substance Registry Services
  35. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  36. PATENTSCOPE (WIPO)
CONTENTS