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Imiprothrin

PubChem CID
123622
Structure
Imiprothrin_small.png
Imiprothrin_3D_Structure.png
Molecular Formula
Synonyms
  • Imiprothrin
  • 72963-72-5
  • Pralle
  • Pralle T
  • Imiprothrin [ISO]
Molecular Weight
318.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-11
Description
Imiprothrin is mixture of 20% (1R)-cis- (CHEBI:39372) and 80% (1R)-trans- (CHEBI:39373) isomers. It has a role as a pyrethroid ester insecticide. It is a member of cyclopropanes and an imidazolidinone. It contains a (1R)-cis-imiprothrin and a (1R)-trans-imiprothrin. It is functionally related to a chrysanthemic acid.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Imiprothrin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2,5-dioxo-3-prop-2-ynylimidazolidin-1-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C17H22N2O4/c1-6-7-18-9-13(20)19(16(18)22)10-23-15(21)14-12(8-11(2)3)17(14,4)5/h1,8,12,14H,7,9-10H2,2-5H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CC(=CC1C(C1(C)C)C(=O)OCN2C(=O)CN(C2=O)CC#C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C17H22N2O4
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 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 KEGG ID

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

imiprothrin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
318.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
318.15795719 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
318.15795719 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
66.9 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
622
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
2
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

Viscous brown liquids or solids; [EXTOXNET]

3.2.2 Color / Form

Viscous liquid
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 712

3.2.3 Flash Point

110 °C
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf

3.2.4 Solubility

In water, 93.5 mg/l @ 25 °C
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 712

3.2.5 Density

1.1 g/cu cm
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 712
Liquid; color: golden yellow (amber); odor: sweet (slightly sweet); density: 0.979 g/ml; vp: 1.39 mm Hg @ 25 °C; log Kow= 2.9; pH=5.22; viscosity: 60 cP; Corrosion: non-corrosive to its commercial packaging, steel cans; stability: stable to metals, metal ions, sunlight and elevated temperature. /Technical grade/
US EPA; Pesticide Fact Sheet. Imiprothrin. Washington, DC: USEPA-737-F-98. Available from, as of Feb 28, 2003: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf

3.2.6 Vapor Pressure

0.00000001 [mmHg]
1.35X10-8 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. 712

3.2.7 LogP

log Kow = 2.9
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 712

3.2.8 Stability / Shelf Life

Stable to metals, metal ions, sunlight & elevated temperature. ... Stable when stored in commercial package (steel cans) for 1 yr.
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf

3.3 Chemical Classes

3.3.1 Pesticides

Pesticides -> Pyrethrins/Pyrethroids
Pesticide (Imiprothrin) -> USDA PDB

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 3
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NIST Number
378573
Library
Main library
Total Peaks
156
m/z Top Peak
123
m/z 2nd Highest
81
m/z 3rd Highest
151
Thumbnail
Thumbnail
2 of 3
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Source of Spectrum
Prof. L. Mondello (Chromaleont s.r.l./Univ. Messina, Italy)
Source of Sample
Sigma-Aldrich Cat. #33442
Copyright
Database Compilation Copyright © 2023-2024 John Wiley and Sons, Inc. Copyright © 2023-2024 John Wiley and Sons, Inc., Portions Copyright Wiley-VCH GmbH, Adams Library under license from Diablo Analytical. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 9
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Authors
Beck B, Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
Instrument
Q Exactive Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
11.7 min
Precursor m/z
319.1652
Precursor Adduct
[M+H]+
Top 5 Peaks

151.1118 999

123.1168 574

163.1117 225

135.1168 193

301.1544 112

Thumbnail
Thumbnail
License
CC BY
2 of 9
View All
Authors
Beck B, Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
Instrument
Q Exactive Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30 (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
11.7 min
Precursor m/z
319.1652
Precursor Adduct
[M+H]+
Top 5 Peaks

123.1168 999

151.1118 377

135.1168 354

163.1117 290

81.0699 193

Thumbnail
Thumbnail
License
CC BY

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Insecticide

7.2 USDA Pesticide Data Program

8 Pharmacology and Biochemistry

8.1 Absorption, Distribution and Excretion

Male and female rats receiving a single oral dose of labeled imiprothrin at 1 or 200 mg/kg eliminated almost all of the radioactivity within 7 days. More than 83% of the radioactivity was excreted in the urine. 14C-residues were generally low in all dosed groups with no marked sex-related differences in excretion rates or tissue residues.
Saito K et al; J Pesticide Sci 20(4): 529-540 (1995)

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Pyrethrins are insecticides used mainly in households; Also used to kill insects on pets and in grain storage bins and poultry pens. Dusts containing 0.3% to 0.5% pyrethrins are used on crops. [EXTOXNET]
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
For Imiprothrin (USEPA/OPP Pesticide Code: 004006) 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 Imiprothrin (72963-72-5). Available from, as of April 21, 2003: https://npirspublic.ceris.purdue.edu/ppis/
Insecticide
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium, 11 th ed., British Crop Protection Council, Surrey, England 1997, p. 712

9.1.1 Household Products

Household & Commercial/Institutional Products

Information on 32 consumer products that contain Imiprothrin in the following categories is provided:

• Inside the Home

• Pesticides

9.2 Formulations / Preparations

Pralle (50.5% imiprothrin)
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet - Imiprothrin. EPA 737-F-98 March 1998. Available from, as of April 21, 2003: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
Multicide Intermediate 2734 (16% imiprothrin, 11.2% d-phenothrin, 52.8% MGK 264)
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet - Imiprothrin. EPA 737-F-98 March 1998. Available from, as of April 21, 2003: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
Multicide Pressurized Roach Spray 27341 (0.4% imiprothrin, 0.5% d-phenothrin, 1% MGK 264)
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet - Imiprothrin. EPA 737-F-98 March 1998. Available from, as of April 21, 2003: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
Raid Ant & Roach 17 (0.1% imiprothrin, 0.1% cypermethrin)
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet - Imiprothrin. EPA 737-F-98 March 1998. Available from, as of April 21, 2003: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf

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

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

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

P264, P270, P273, P301+P317, P330, 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 51 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

Acute Tox. 4 (100%)

Acute Tox. 4 (28.4%)

Carc. 2 (28.4%)

STOT SE 2 (28.4%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

10.1.3 Hazards Summary

Pyrethroids have low toxicity to humans after dermal exposure. Of 573 dermal or ingestion poisoning cases in China, 51 patients had disturbed consciousness and 34 had seizures. Of those, only five were occupationally exposed. Seizures are more commonly related to exposures to fenvalerate, flucythrinate, cypermethrin, deltapermethrin, and fluvalinate. Seizures have not been reported after exposure to permethrin. Pyrethroids may also cause paresthesias after skin contact. Paresthesias (stinging and numbness) usually begin 1-2 hours after contact and resolve within 24 hours. [EPA Pesticides, p. 87-8] Pyrethrins cause liver injury when fed to animals at high doses. [EXTOXNET]

10.2 Accidental Release Measures

10.2.1 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.

10.3 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Environmental tox

Authoritative List - CWA 303(d)

Report - if used as a fragrance or flavor ingredient

REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Imiprothrin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

11 Toxicity

11.1 Toxicological Information

11.1.1 Adverse Effects

Neurotoxin - Other CNS neurotoxin

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

11.1.2 Antidote and Emergency Treatment

Basic treatment: . Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. 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. Administer activated charcoal ... . /Pyrethrins, pyrethroids, and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 269
Advanced treatment: Consider orotracheal or nasotracheal intubation for air way control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias if 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 ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Pyrethrins, pyrethroids, and related compounds/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 269-70

11.1.3 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Technical grade: Primary eye irritation: rabbit, non-irritating. Primary skin irritation: rabbit, non-irritating.
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ A 13-wk oral rat study showed significant body weight loss and suppression of feeding rate at doses of 3,000, 6,000 or 10,000 ppm. Hematology and blood chemistry values were also altered at these doses as compared to the lowest dose (100 ppm) and the control group. The weights of the liver and other organs increased in the three highest dose groups. The NOEL was judged to be 100 ppm and the LOEL to be 3,000 ppm.
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ A 21 day dermal study with rats conducted at 100, 300 or 1,000 mg/kg bw showed an incr in the incidence of dermal acanthosis and hyperkeratosis in the high dose group. The NOEL was 300 mg/kg bw based on these effects and the LOEL was 1,000 mg/kg bw/day.
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ A 4-wk inhalation study exposed rats to 2.4, 22.0 or 186 mg/cu m of imiprothrin with a median aerodynamic diameter of 0.80-0.86 um. The NOEL was 22.0 mg/cu m based on lower total body weight gain, changes in hematology and clinical chemistry parameters, and changes in liver and the salivary glands. The LOEL was 186 mg/m3.
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
For more Non-Human Toxicity Excerpts (Complete) data for IMIPROTHRIN (15 total), please visit the HSDB record page.

11.1.4 Non-Human Toxicity Values

LD50 Rat dermal >2000 mg/kg
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
LD50 Rat (female) oral 900 mg/kg
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
LD50 Rat (male) oral 1800 mg/kg
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
LD50 Rat (male) oral 4500 mg/kg /Pralle (50.0% imiprothrin)/
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf
For more Non-Human Toxicity Values (Complete) data for IMIPROTHRIN (9 total), please visit the HSDB record page.

11.2 Ecological Information

11.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

11.2.2 Ecotoxicity Values

EC50 Daphnia magna 0.051 ppm /Conditions of bioassay not specified/
US EPA; Pesticide Fact Sheet. Imiprothrin. EPA-737-F-98 March 1998. Washington, DC: USEPA, Off Prev Pest Tox Sub (7505C). Available from, as of April 15, 2002: https://www.epa.gov/opprd001/factsheets/imiprothrin.pdf

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: Risk Category of Japanese OTC Drugs

17.4 KEGG: OTC drugs

17.5 ChemIDplus

17.6 UN GHS Classification

17.7 EPA CPDat Classification

17.8 NORMAN Suspect List Exchange Classification

17.9 EPA DSSTox Classification

17.10 Consumer Product Information Database Classification

17.11 EPA Substance Registry Services Tree

17.12 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. California Safe Cosmetics Program (CSCP) Product Database
  2. 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
    imiprothrin (ISO); reaction mass of [2,5-dioxo-3-(prop-2-yn-1-yl)imidazolidin-1-yl]methyl (1R,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate and [2,5-dioxo-3-(prop-2-yn-1-yl)imidazolidin-1-yl]methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate
    https://chem.echa.europa.eu/100.102.716
    imiprothrin (ISO); reaction mass of [2,5-dioxo-3-(prop-2-yn-1-yl)imidazolidin-1-yl]methyl (1R,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate and [2,5-dioxo-3-(prop-2-yn-1-yl)imidazolidin-1-yl]methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate (EC: 428-790-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/92389
  3. 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/
  4. 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/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. Hazardous Substances Data Bank (HSDB)
  8. ChEBI
  9. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  10. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. 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://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  11. EPA Chemical and Products Database (CPDat)
  12. 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
  13. EPA Pesticide Ecotoxicity Database
  14. Hazardous Chemical Information System (HCIS), Safe Work Australia
  15. 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
    imiprothrin (ISO); reaction mass of:...
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  16. USDA Pesticide Data Program
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. 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
    Risk category of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08312.keg
    Classification of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08313.keg
  19. MassBank Europe
  20. 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
  21. Metabolomics Workbench
  22. 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
  23. SpectraBase
  24. Springer Nature
  25. Wikidata
  26. Wikipedia
  27. PubChem
  28. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  29. GHS Classification (UNECE)
  30. 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/
  31. EPA Substance Registry Services
  32. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  33. PATENTSCOPE (WIPO)
  34. NCBI
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