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Hexaflumuron

PubChem CID
91741
Structure
Hexaflumuron_small.png
Hexaflumuron_3D_Structure.png
Molecular Formula
Synonyms
  • Hexaflumuron
  • 86479-06-3
  • Recruit
  • Hexaflumuron [ISO]
  • N-[[3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]carbamoyl]-2,6-difluorobenzamide
Molecular Weight
461.1 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
Hexaflumuron is an N-acylurea that is urea in which a hydrogen attached to one of the nitrogens is replaced by a 2,6-difluorobenzoyl group, while a hycrogen attached to the other nitorgen is replaced by a 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl group. It is a benzoylurea insecticide, an organofluorine insecticide, an organochlorine insecticide, a dichlorobenzene, a N-acylurea and an aromatic ether.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Hexaflumuron.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[[3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]carbamoyl]-2,6-difluorobenzamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C16H8Cl2F6N2O3/c17-7-4-6(5-8(18)12(7)29-16(23,24)14(21)22)25-15(28)26-13(27)11-9(19)2-1-3-10(11)20/h1-5,14H,(H2,25,26,27,28)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C(=C2)Cl)OC(C(F)F)(F)F)Cl)F
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H8Cl2F6N2O3
C16H8Cl2F6N2O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

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 ICSC Number

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 Nikkaji Number

2.3.13 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • hexaflumuron
  • hexafluoron
  • insecticide Sonet
  • N-(((3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-2,6-difluorobenzamide
  • XRD 473
  • XRD-473

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
461.1 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
5.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
459.9816165 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
459.9816165 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
67.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
581
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
0
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 or white solid; [ICSC]
WHITE CRYSTALS OR POWDER.

3.2.2 Color / Form

White solid
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. 676

3.2.3 Melting Point

202-205 °C
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 676

3.2.4 Solubility

Methanol 11.3, xylene 5.2 (both g/l @ 20 °C)
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 676
In water, 0.027 mg/l @ 18 °C
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 676
Solubility in water, mg/l at 18 °C: 0.027 (practically insoluble)

3.2.5 Density

Relative density (water=1): 1.7
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm
Density (at 20 °C): 1.68 g/cm³

3.2.6 Vapor Pressure

0.00000044 [mmHg]
4.43X10-7 mm Hg @ 25 °C
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 676
Vapor pressure at 25 °C: negligible

3.2.7 LogP

log Kow = 5.68
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 676
5.46

3.2.8 Stability / Shelf Life

Undergoes 60% hydrolysis in 35 days (pH 9). Photolysis DT50 6.3 days (pH 5.0, 25 °C).
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 564

3.2.9 Decomposition

Photolysis DT50 6.3 days (pH 5.0, 25 °C).
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 564
The substance decomposes on burning producing toxic and corrosive fumes including nitrogen oxides, hydrogen chloride, hydrogen fluoride.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm
below boiling point

3.2.10 Collision Cross Section

188.22 Ų [M+H]+ [CCS Type: TW]

202.62 Ų [M+Na]+

187.85 Ų [M+H]+

S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

3.3 Chemical Classes

3.3.1 Pesticides

Insecticides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Active substance -> EU Pesticides database: Not approved
Pesticides -> Other Insecticides

3.3.2 PFAS

PFAS -> Other/unspecified
S14 | KEMIPFAS | PFAS Highly Fluorinated Substances List from KEMI | DOI:10.5281/zenodo.2621524
PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
S100 | PFASREACH | List of PFAS identified in REACH 2019 | DOI:10.5281/zenodo.7426856

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 19F NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 MS-MS

NIST Number
1186976
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
460.9889
Total Peaks
11
m/z Top Peak
158
m/z 2nd Highest
140.9
m/z 3rd Highest
277.9
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4.2.2 LC-MS

1 of 32
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Authors
F. Jud [dtc], K. Arturi [dtc], J. Hollender [dtc], A. Dax [com]
Instrument
Q Exactive Plus
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
13.338 min
Precursor m/z
460.9889
Precursor Adduct
[M+H]+
Top 5 Peaks

158.041 999

141.0146 58

277.9756 21

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License
CC BY-SA
2 of 32
View All
Authors
F. Jud [dtc], K. Arturi [dtc], J. Hollender [dtc], A. Dax [com]
Instrument
Q Exactive Plus
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
13.338 min
Precursor m/z
460.9889
Precursor Adduct
[M+H]+
Top 5 Peaks

158.041 999

141.0145 238

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License
CC BY-SA

4.2.3 Other MS

1 of 6
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Authors
Rennie E, McEachran A, Agilent Technologies
Instrument Type
ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
40
Precursor m/z
458.9743403
Precursor Adduct
[M-H]-
Top 5 Peaks

174.959231 999

199.953665 130

113.02083 86

93.014602 85

96.990673 73

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License
CC BY
2 of 6
View All
Authors
Rennie E, McEachran A, Agilent Technologies
Instrument Type
ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
40
Precursor m/z
460.9888932
Precursor Adduct
[M+H]+
Top 5 Peaks

141.014648 999

158.040054 471

142.017307 51

113.019733 38

140.030632 37

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License
CC BY

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Insecticide
Pesticide active substances -> Insecticides
Insecticides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

7.2 EU Pesticides Data

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

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Insecticides
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

8.2 Absorption, Distribution and Excretion

The substance can be absorbed into the body by inhalation.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Used as insecticide (inhibits chitin production); [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.
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
For Hexaflumuron (USEPA/OPP Pesticide Code: 118202) ACTIVE products with label matches. /SRP: Registered for 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 Hexaflumuron (86479-06-3). Available from, as of June 26, 2002: https://npirspublic.ceris.purdue.edu/ppis/
/Control of Lepidoptera, Coleoptera, Homoptera, and Diptera on top fruit, cotton, and potatoes/
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. 836
Insecticide
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. 836

9.1.1 Use Classification

Insecticides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

9.1.2 Household Products

Household & Commercial/Institutional Products

Information on 1 consumer products that contain Hexafluoron in the following categories is provided:

• Pesticides

9.2 Methods of Manufacturing

RH Rigterink, RJ Sbragia, EP 71279; eidem, US 4,468,405 (1983, 1984 both to Dow)
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. 836

9.3 Formulations / Preparations

USEPA/OPP Pesticide Code 118202; Trade Names: DE-473, NAF-46.
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Hexaflumeron (86479-06-3). Available from, as of June 26, 2002: https://npirspublic.ceris.purdue.edu/ppis/
Mixtures: [hexaflumuron] chloropyrifos
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 676
Emulsifiable concentrate; suspension concentrate
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 676
Recruit (0.1% Hexaflumuron), Recruit AG (0.5% Hexaflumuron, 99.5% inert ingredients), Recruit 50% Concentrate, Recruit II (0.5% Hexaflumuron, 99.5% inert ingredients)
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Hexaflumuron (86479-06-3). Available from, as of April 23, 2003: https://npirspublic.ceris.purdue.edu/ppis/

9.4 General Manufacturing Information

Mode of action: Systemic insecticide. Inhibits chitin synthesis.
Blacow, N. W. (ed.). Martindale: The Extra Pharmacopoeia. 26th ed. London: The Pharmaceutical Press, 1972., p. 564
The Sentricon Termite Colony Elimination System ... was launched commercially in 1995 after receiving EPA registration as a reduced risk pesticide. Sentricon represents truly novel technology employing an Integrated Pest Management approach using monitoring and targeted delivery of a highly specific bait. ... The properties of hexaflumuron as a termite control agent are attractive from an environmental and human risk perspective, but more importantly, the potential for adverse affects is dramatically reduced since it is present only in very small quantities in stations with termite activity. The comparisons to barrier methods show significant reduction in the use of hazardous materials and substantial reduction in potential impacts on human health and the environment.[
Environmental Protection Agency; 2000 Presidential Green Chemistry Challenge; Dow AgroSciences Sentricon Termite Colony Elimination System, A New Paradigm for Termite Control. Available from: https://www.epa.gov/opptintr/greenchemistry/dsca00.htmlas of May 27, 2003]

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 4
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Pictogram(s)
Irritant
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H332 (40.9%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P261, P271, P273, P304+P340, P317, P391, 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 93 reports by companies from 2 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

Acute Tox. 4 (40.9%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

Acute Tox. 4 (97.4%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

10.1.3 Fire Hazards

Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

10.1.4 Hazards Summary

Rats were given orally up to 100 mg/kg for 28 days; No overt signs of toxicity, but reticulocyte counts were increased; [HSDB] May induce methemoglobinemia; [ICSC] May cause irritation; [MSDSonline]

10.1.5 Fire Potential

Liquid formulations containing organic solvents may be flammable.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

10.1.6 Skin, Eye, and Respiratory Irritations

Evaporation at 20 °C is negligible; a nuisance-causing concn of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

10.2 First Aid Measures

Inhalation First Aid
Fresh air, rest.
Skin First Aid
Rinse and then wash skin with water and soap.
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Rinse mouth.

10.3 Fire Fighting

In case of fire in the surroundings, use appropriate extinguishing media.

10.3.1 Fire Fighting Procedures

In case of fire in the surroundings: all extinguishing agents allowed.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

10.4 Accidental Release Measures

10.4.1 Spillage Disposal

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

10.4.2 Cleanup Methods

Do NOT wash away into sewer. Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. ... Provision to contain effluent from fire extinguishing.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

10.4.3 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.

10.4.4 Preventive Measures

Do not eat, drink, or smoke during work. Wash hands before eating.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

10.5 Handling and Storage

10.5.1 Safe Storage

Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

10.5.2 Storage Conditions

/Keep/ separated from food and feedstuffs. Well closed.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

10.6 Exposure Control and Personal Protection

10.6.1 Inhalation Risk

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

10.6.2 Effects of Long Term Exposure

The substance may have effects on the blood. This may result in the formation of methaemoglobin.

10.6.3 Personal Protective Equipment (PPE)

Protective gloves. Safety spectacles. ...Extra personal protection /for cleanup/: P2 filter respirator for harmful particles).
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

10.6.4 Preventions

Exposure Prevention
PREVENT DISPERSION OF DUST!
Inhalation Prevention
Avoid inhalation of dust.
Skin Prevention
Protective gloves.
Eye Prevention
Wear safety spectacles.
Ingestion Prevention
Do not eat, drink, or smoke during work.

10.7 Transport Information

10.7.1 Packaging and Labelling

Do not transport with food and feedstuffs.

10.7.2 UN Classification

UN Hazard Class: 9; UN Pack Group: III

10.8 Regulatory Information

Status Regulation (EC)
2004/129/EC
REACH Registered Substance

10.8.1 FIFRA Requirements

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 118202; Tpye of Pesticide: conventional-insecticide/termiticide; Use Site: non-food use, wood, ornamentals; Year: 1994.
USEPA/OPP; Status of Pesticides in Registration, Reregistration and Special Review p.373 (Spring, 1998) EPA 738-R-98-002

10.9 Other Safety Information

10.9.1 Toxic Combustion Products

Gives off irritating or toxic fumes (or gases) in a fire.
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

11 Toxicity

11.1 Toxicological Information

11.1.1 Exposure Routes

The substance can be absorbed into the body by ingestion and by inhalation of dust.

11.1.2 Adverse Effects

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

11.1.3 Acute Effects

11.1.4 Toxicity Data

LC50 (rat) > 2,500 mg/m3/4h

11.1.5 Antidote and Emergency Treatment

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139
First Aid: Inhalation exposure: Fresh air, rest. Skin exposure: Rinse skin with plenty of water or shower. Eyes exposure: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. /from table/
IPCS, CEC; International Chemical Safety Card on Hexaflumuron. (October 1995). Available from, as of April 23, 2003: https://www.inchem.org/documents/icsc/icsc/eics1266.htm

11.1.6 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The effects of five benzoylphenylurea insecticides /including/ ...hexaflumuron... were comparatively evaluated on hematological parameters in rats. Sixty adult Wistar-rats were divided into five dose groups and a control group. Daily doses of 100 mg/kg of each tested insecticide were administered by gavage for 28 days, after which rats were sacrificed and blood was taken for examination. Parameters measured were red blood cell count, hemoglobin (Hb), hematocrit, mean corpuscular volume, mean corpuscular Hb concentration, methemoglobin (metHb), and reticulocyte counts. Results showed that treatment with insecticides at the dose given did not produce any overt signs of toxicity. ...The reticulocyte level was increased in all treated groups, even at dose levels of 50mg/kg. The authors conclude that the metHb level incr and reticulocyte incr are the most sensitive parameters, but that one might be independent of the other.
Tasheva M, Hristeva V; Journal of Applied Toxicology 13 (1): 67-68 (1993).

11.1.7 Non-Human Toxicity Values

LD50 Rat oral >5000 mg/kg
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 564
LD50 Rat percutaneous >5000 mg/kg
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 564

11.2 Ecological Information

11.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

11.2.2 Ecotoxicity Values

LD50 Mallard ducks oral >2000 mg/kg
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 564
LD50 Bee oral & contact >0.1 mg/bee
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 564

11.2.3 Ecotoxicity Excerpts

/AQUATIC SPECIES/ Hexaflumuron, an insect growth regulator (IGR), was found to be nonlethal to four species of larvivorous fish, Poecilia reticulata, Gambusia affinis, Aplocheilus blochii and Tilapia mossambica at | 1.0 mg/l. These species were found to be tolerant with higher LD50 values ranging from 2.21-3.097 mg/l. Absolute survival (100%) was observed in all the four species at 1.0 mg/l for more than 8 days. Fish safety factor or suitability index computed for each fish species against the three vector mosquitoes showed maximum value for P. reticulata which indicated its higher tolerance than other species. Fishes that exhibited decreased swimming activity on exposure at 1.0 mg/l regained normal activity on withdrawal of exposure. No adverse effect was noticed in the reproduction of G. affinis.
Vasuki V; Indian J Exp Biol 30 (12): 1163-1165 (1992).

11.2.4 ICSC Environmental Data

The substance is very toxic to aquatic organisms. Bioaccumulation of this chemical may occur in fish. The substance may cause long-term effects in the aquatic environment. Avoid release to the environment in circumstances different to normal use.

11.2.5 Environmental Fate / Exposure Summary

Hexaflumuron's production may result in its release to the environment through various waste streams; it's use as an insecticide will result in its direct release to the environment. If released to air, a vapor pressure of 4.43X10-7 mm Hg at 25 °C indicates hexaflumuron will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase hexaflumuron will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 18.3 hrs. Particulate-phase hexaflumuron will be removed from the atmosphere by wet and dry deposition. Hexaflumuron absorbs light in the environmental UV spectrum and has the potential for direct photolysis. If released to soil, hexaflumuron is expected to have no mobility based upon an estimated Koc of 29,300. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 1.0X10-5 atm-cu m/mole. However, adsorption to soil is expected to attenuate volatilization. In soil, the biodegradation half-life for hexaflumuron ranged from 56 to 190 days under aerobic conditions. Under anaerobic conditions, the biodegradation half-life for hexaflumuron ranged from 40-64 days. If released into water, hexaflumuron is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 2.2 hrs and 8.5 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. An estimated BCF of 4,700 suggests the potential for bioconcentration in aquatic organisms is very high. The hydrolysis of hexaflumuron in natural water was a first order process with a mean half-life of 42.3 days. Photodegradation in water was a first order process with a half-life of approx 6.3 days. Occupational exposure to hexaflumuron may occur by dermal contact with this compound at workplaces where hexaflumuron is produced or used. (SRC)

11.2.6 Artificial Pollution Sources

Hexaflumuron's production may result in its release to the environment through various waste streams; it's use as an insecticide(1,2) will result in its direct release to the environment(SRC).
(1) Tomlin CDS, ed; The Pesticide Manual World Compendium. 11th ed, Surrey, England: British Crop Protection Council, p 676 (1997)
(2) Budavari S, ed; The Merck Index. Whitehouse Station, NJ: Merck and Co Inc, p. 836 (2001)

11.2.7 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 29,300(SRC), determined from a log Kow of 5.68(2) and a regression-derived equation(3), indicates that hexaflumuron is expected to be immobile in soil(SRC). Volatilization of hexaflumuron from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 4.43X10-7 mm Hg(2), and water solubility, 0.027 mg/l(2). Hexaflumuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). However, adsorption to soil is expected to attenuate volatilization(SRC). In soil, the aerobic biodegradation half-life for hexaflumuron ranged from 56 to 190 days under different moisture and temperature conditions(4). Under anaerobic conditions, the biodegradation half-life for hexaflumuron ranged from 40-64 days at 25 °C(4). Photodegradation of hexaflumuron may be important since it has a half-life in water of 6.3 days(4).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Tomlin CDS, ed; The Pesticide Manual World Compendium. 11th ed, Surrey, England: British Crop Protection Council, p 676 (1997)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(4) Yon D et al; pp. 907-12 in Brighton Crop Prot Conf. Pest Dis (1992)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 29,300(SRC), determined from a log Kow of 5.68(2) and a regression-derived equation(3), indicates that hexaflumuron is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 4.4X10-7 mm Hg(2), and water solubility, 0.027 mg/l(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.2 hrs and 8.5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 290 months if adsorption is considered(4). According to a classification scheme(5), an estimated BCF of 4,700(SRC), from its log Kow (2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Based on soil biodegradation studies, hexaflumuron is expected to biodegrade in water under aerobic and anaerobic conditions(SRC). In soil the aerobic biodegradation half-life for hexaflumuron ranged from 56 to 190 days under different moisture and temperature conditions(7). Under anaerobic conditions in soil, the biodegradation half-life for hexaflumuron ranged from 40-64 days at 25 °C(7). The hydrolysis of hexaflumuron in natural water was a first order process with a mean half-life of 42.3 days(7). The aqueous photolysis of hexaflumuron resulted in 2,6-difluorobenzamide, 3,5-dichloro-4-hydroxyaniline, and CO2 as the major degradation products. The photodegradation was a first order process with a half-life of approx 6.3 days(7).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Tomlin CDS, ed; The Pesticide Manual World Compendium. 11th ed, Surrey, England: British Crop Protection Council, p. 676 (1997)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) US EPA; EXAMS II Computer Simulation (1987)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(7) Yon D et al; pp. 907-12 in Brighton Crop Prot Conf. Pest Dis (1992)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexaflumuron, which has a vapor pressure of 4.43X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase hexaflumuron is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 18.3 hrs(SRC), calculated from its rate constant of 21X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase hexaflumuron may be removed from the air by wet and dry deposition(SRC). Based on aqueous photolysis studies(2), hexaflumuron has the potential for direct photolysis(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Tomlin CDS, ed; The Pesticide Manual World Compendium. 11th ed, Surrey, England: British Crop Protection Council, p. 676 (1997)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

11.2.8 Environmental Biodegradation

AEROBIC: Hexaflumuron biodegrades under aerobic conditions(SRC). Levels of radioactivity in the 14CO2 traps from and aerobic soil degradation experiment were very low with a total of only 0.7-2.1% of the applied activity observed 84 days after treatment with (14C-aniline)hexaflumuron(1). However, previous investigations using benzoyl 14C-labeled hexaflumuron have shown greater amounts of 14CO2 suggesting that this part of the molecule is more readily degraded to CO2(1). TLC of the extracts of the soil samples incubated under aerobic conditions showed the presence of two metabolites, 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline and 2,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenylurea in addition to the parent(1). Levels of both metabolites generally increased with incubation time, and the greatest levels were observed at the higher temperatures and moisture contents(1). The half-life of (14C-aniline)hexaflumuron in Castle Rising soil under different temperature and moisture regimes were as follows: 159 days (moisture, 50% of 0.33 bar; 25 °C); 90 days (moisture, 75% of 0.33 bar; 25 °C); 64 days (moisture, 100% of 0.33 bar; 25 °C); 190 days (moisture, 75% of 0.33 bar; 10 °C); 90 days (moisture, 75% of 0.33 bar; 25 °C); 56 days (moisture, 75% of 0.33 bar; 35 °C)(1).
(1) Yon D et al; pp. 907-12 in Brighton Crop Prot Conf. Pest Dis (1992)
ANAEROBIC: Analysis of the anaerobic soils showed the presence of 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline as the major metabolite (8-18% of applied activity), with an unknown metabolite of greater polarity than any of the reference standards observed at levels up to 5% of applied radioactivity(1). Half-lives of (14C-aniline)hexaflumuron at 25 °C under anaerobic conditions were in the range 40-64 days(1).
(1) Yon D et al; pp. 907-12 in Brighton Crop Prot Conf. Pesti Dis (1992)

11.2.9 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of hexaflumuron with photochemically-produced hydroxyl radicals has been estimated as 21X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18.3 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hexaflumuron is hydrolytically stable in sterile buffers at pH 5.0, is slowly degraded at pH 7.0 (6% breakdown in 33 days) and is more rapidly degraded at pH 9.0 (approx 60% breakdown in 33 days)(2). Hydrolysis at pH 9.0 proceeds by 2 separate routes, with the more facile producing 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenylurea and 2,6-difluorobenzoic acid, and the slower producing 3,5-dicloro-4-(1,1,2,2-tetrafluoroethoxy)phenylurea and 2,6-difluorobenzamide(2). The overall disappearance of hexaflumuron was a first order process with a half-life of 22 days(2). The hydrolysis of hexaflumuron in natural water was also a first order process with a mean half-life of 42.3 days and resulted in the formation of 2,6-difluorobenzoic acid and two unknown products, one of which was tentatively identified as 3,5-dicloro-4-(1,1,2,2-tetrafluoroethoxy)phenylurea(2). The aqueous photolysis of hexaflumuron resulted in 2,6-difluorobenzamide, 3,5-dichloro-4-hydroxyaniline, and CO2 as the major degradation products. The photodegradation was a first order process with a half-life of approx 6.3 days(2).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Yon D et al, pp. 907-12 in Brighton Crop Prot Conf. Pest Dis (1992)

11.2.10 Environmental Bioconcentration

An estimated BCF of 4,700 was calculated for hexaflumuron(SRC), using a log Kow of 5.68(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).
(1) Tomlin CDS, ed; The Pesticide Manual World Compendium. 11th ed, Surrey, England: British Crop Protection Council, p. 676 (1997)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.11 Soil Adsorption / Mobility

Hexaflumuron is strongly adsorbed on a wide range of soils(1,4). The Koc of hexaflumuron is estimated as 29,300(SRC), using a log Kow of 5.68(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that hexaflumuron is expected to be immobile in soil(SRC). Soil Kd (desorption constants) values ranged from 147 to 1,326(4) and soil Kom values ranged from 3,096 to 41,170(1).
(1) Tomlin CDS, ed; The Pesticide Manual World Compendium. 11th ed, Surrey, England: British Crop Protection Council, p. 676 (1997)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 17-28 (1983)
(4) Yon D et al, pp. 907-12 in Brighton Crop Prot Conf. Pest Dis (1992)

11.2.12 Volatilization from Water / Soil

The Henry's Law constant for hexaflumuron is estimated as 1.0X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 4.43X10-7 mm Hg(1), and water solubility, 0.027 mg/l(1). This Henry's Law constant indicates that hexaflumuron is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 2.2 hrs(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 8.5 days(SRC). Hexaflumuron's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from moist soil and water surfaces is expected to be attenuated by adsorption(SRC). The estimated volatilization half-life from a model pond is 290 months if adsorption is considered(3). Hexaflumuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
(1) Tomlin CDS, ed; The Pesticide Manual World Compendium. 11th ed, Surrey, England: British Crop Protection Council, p. 676 (1997)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) US EPA; EXAMS II Computer Simulation (1987)

11.2.13 Probable Routes of Human Exposure

Occupational exposure to hexaflumuron may occur by dermal contact with this compound at workplaces where hexaflumuron is produced or used. (SRC)

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Chemical Co-Occurrences in Literature

13.5 Chemical-Gene Co-Occurrences in Literature

13.6 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 UN GHS Classification

17.6 NORMAN Suspect List Exchange Classification

17.7 CCSBase Classification

17.8 EPA DSSTox Classification

17.9 Consumer Product Information Database Classification

17.10 PFAS and Fluorinated Organic Compounds in PubChem

17.11 EPA Substance Registry Services Tree

17.12 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
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    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)
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    https://echa.europa.eu/web/guest/legal-notice
    hexaflumuron (ISO); 1-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)-3-(2,6-difluorobenzoyl)urea
    https://chem.echa.europa.eu/100.100.333
    hexaflumuron (ISO); 1-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)-3-(2,6-difluorobenzoyl)urea (EC: 401-400-1)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/70428
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  7. ILO-WHO International Chemical Safety Cards (ICSCs)
  8. Risk Assessment Information System (RAIS)
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    Hexaflumuron
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    https://www.norman-network.com/nds/SLE/
  11. ChEBI
  12. ChEMBL
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    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  15. EPA Pesticide Ecotoxicity Database
  16. EU Pesticides Database
  17. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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  19. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
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  25. Metabolomics Workbench
  26. NIST Mass Spectrometry Data Center
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    https://www.nist.gov/srd/public-law
  27. SpectraBase
    N-[[3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]carbamoyl]-2,6-difluorobenzamide
    https://spectrabase.com/spectrum/7XazzPPfvUz
  28. Springer Nature
  29. Wikidata
  30. PubChem
  31. Medical Subject Headings (MeSH)
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  32. GHS Classification (UNECE)
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  34. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  35. PATENTSCOPE (WIPO)
CONTENTS