An official website of the United States government

Permethrin

PubChem CID
40326
Structure
Permethrin_small.png
Permethrin_3D_Structure.png
Molecular Formula
Synonyms
  • Permethrin
  • 52645-53-1
  • Pounce
  • Permethrine
  • Permetrina
Molecular Weight
391.3 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-18
Description
Permethrin is a pale brown liquid. Relatively water insoluble. Used as an insecticide.
Permethrin is a cyclopropanecarboxylate ester in which the esterifying alcohol is 3-phenoxybenzyl alcohol and the cyclopropane ring is substituted with a 2,2-dichlorovinyl group and with gem-dimethyl groups. It has a role as a pyrethroid ester insecticide, a pyrethroid ester acaricide, an agrochemical, an ectoparasiticide and a scabicide. It is a member of cyclopropanes and a cyclopropanecarboxylate ester. It is functionally related to a 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid.
A pyrethroid insecticide commonly used in the treatment of lice infestations and scabies. It is a yellow to light orange-brown, low melt-ing solid or viscous liquid.
See also: Pediculicide (subclass of); trans-Permethrin (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Permethrin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

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

2.1.4 SMILES

CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H20Cl2O3
Computed by PubChem 2.2 (PubChem release 2024.11.20)
C21Cl2H20O3
C21H20Cl2O3

2.3 Other Identifiers

2.3.1 CAS

52645-53-1
52341-32-9
52341-33-0
93389-07-2

2.3.2 Deprecated CAS

57608-04-5, 60018-94-2, 63364-00-1, 75497-64-2, 93388-66-0
60018-94-2, 63364-00-1, 75497-64-2, 93388-66-0

2.3.3 European Community (EC) Number

2.3.4 UN Number

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 ICSC Number

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 NSC Number

2.3.16 PharmGKB ID

2.3.17 RXCUI

2.3.18 Wikidata

2.3.19 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (m-Phenoxybenzyl)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • 3-Phenoxybenzyl-(+-)-cis,trans-2,2-dichlorovinyl-2,2-dimethyl-cyclopropylcarboxylic acid, ester
  • 3-Phenoxybenzyl-cis,trans-(1RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
  • Ambush
  • cis permethrin
  • cis-(1RS)-permethrin
  • cis-permethrin
  • Cyclopropanecarboxylic Acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
  • Elimite
  • FMC 33297
  • FMC-33297
  • FMC33297
  • NIA 33297
  • NIA-33297
  • NIA33297
  • Nittifor
  • NRDC 143
  • NRDC 147
  • NRDC-143
  • NRDC-147
  • NRDC143
  • NRDC147
  • Permethrin
  • Permethrin, (1R-cis)-Isomer
  • Permethrin, (1R-trans)-Isomer
  • Permethrin, (1S-cis)-Isomer
  • Permethrin, (1S-trans)-Isomer
  • Permethrin, (cis)-Isomer
  • Permethrin, (cis-(+-))-Isomer
  • Permethrin, (trans)-Isomer
  • Permethrin, (trans-(+-))-Isomer
  • permethrin, cis-(1RS)-isomer
  • Permethrin, trans-(1RS)-Isomer
  • PP 557
  • PP-557
  • PP557
  • S 3151
  • S-3151
  • S3151
  • trans permethrin
  • trans-(1RS)-Permethrin
  • trans-permethrin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
391.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
6.5
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
390.0789499 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
390.0789499 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
35.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
26
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
521
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
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

Permethrin is a pale brown liquid. Relatively water insoluble. Used as an insecticide.
Colorless to pale yellow solid or liquid; [Merck Index] Yellow-brown to brown viscous liquid or solid; [ICSC] Solid; mp = 34 deg C; [MSDSonline]
Solid
YELLOW-BROWN-TO-BROWN VISCOUS LIQUID OR CRYSTALS.

3.2.2 Color / Form

Colorless crystals to a viscous liquid; Color, white to pale yellow
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 592
Pure permethrin cis-isomer forms colorless crystals at room temperature but a mixture of cis and trans isomers normally occurs as a liquid, with its appearance depending on the ratio of isomers. Pure permethrin (40:60) is a colorless, viscous liquid, whereas the technical compound is a yellow to yellow-brown viscous liquid.
World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009). Available from, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf

3.2.3 Boiling Point

220 °C at 5.00E-02 mm Hg
PhysProp
>290 °C at 760 mm Hg
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Permethrin (52645-53-1) (2008-2010)
BP: 200 °C at 0.1 mm Hg
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Permethrin (52645-53-1) (2008-2010)

3.2.4 Melting Point

34 °C
PhysProp
<20 °C (OECD Method 102)
World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009). Available from, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
MP: cis-isomers, 63-65 °C; trans-isomers, 44-47 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Permethrin (52645-53-1) (2008-2010)
34 °C
34-39 °C

3.2.5 Solubility

0.006 mg/L (at 20 °C)
USDA PESTICIDE PROP DATABASE
In water, 0.0111 mg/L at 20 °C, pH 7.0-9.3 (OECD Method 105)
World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009). Available from, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
In water, 6.00X10-3 mg/L (pH 7, 20 °C); cis-isomers 0.20 mg/L (25 °C); trans-isomers 0.13 mg/L (25 °C)
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Permethrin (52645-53-1) (2008-2010)
In xylene and hexane >1000, methanol 258 (all in g/kg at 25 °C)
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Permethrin (52645-53-1) (2008-2010)
Soluble in most organic solvents except ethylene glycol. Soluble in acetone, ethanol, ether, and xylene
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 592
In water, 6.00X10-3 mg/ml @ 20 °C.
USDA; Agric Res Service. ARS Pesticide Properties Database on Permethrin (52645-53-1). May 1995. Available from, as of Jan 12, 2001: https://www.usda.gov/wps/portal/usda/usdahome
6.91e-05 g/L
Solubility in water: none

3.2.6 Density

1.19 - 1.27 at 20 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Permethrin (52645-53-1) (2008-2010)
Relative density (water = 1): 1.2

3.2.7 Vapor Pressure

0.00000002 [mmHg]
Vapor pressure: cis-isomers 2.9X10-3 mPa at 25 °C, trans-isomers 9.2X10-4 Pa at 25 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Permethrin (52645-53-1) (2008-2010)
5.18X10-8 mm Hg at 25 °C (OECD Method 104)
World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009). Available from, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
Vapor pressure, Pa at 20 °C:

3.2.8 LogP

6.5
HANSCH,C ET AL. (1995)
log Kow = 6.50
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 171
6.50
HANSCH,C ET AL. (1995)
6.5

3.2.9 Stability / Shelf Life

Stable to heat (> or = 2 yr at 50 °C), more stable in acid than alkaline media with optimum stability ca. pH 4; some photochemical degradation has been observed in laboratory studies but field data indicate this does not adversely affect biological performances.
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 784

3.2.10 Decomposition

When heated to decomp it emits toxic fumes of /hydrogen chloride/.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 122

3.2.11 Corrosivity

Does not corrode aluminum
Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A316/Aug 87

3.2.12 Other Experimental Properties

Mixture of approx 60% trans- and 40% cis-isomers; colorless crystals to a pale yellow viscous liquid; mp: ca 35 °C; bp: 220 °C at 0.05 mm Hg; sp gr: 1.190-1.272 at 20 °C/4 °C; vapor pressure: < 1X10-6 mm Hg at 50 °C; solubility in water: < 1 ppm; sol or miscible with organic solvents except ethylene glycol. /Technical permethrin/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1337
Stable to heat (> 2 yrs at 50 °C), more stable in acid than alkaline media with optimum stability ca. pH 4.
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Permethrin (52645-53-1) (2008-2010)
log Kow: >6.50 at 40 °C (OECD Method 117)
World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009). Available from, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antiparasitic Agents; Insecticides
Human drug -> Prescription
Human drug -> Prescription; Over-the-counter; Discontinued; Active ingredient (PERMETHRIN)
Dermatological medicines &gt; Scabicides and pediculicides
3.3.1.2 Animal Drugs
Veterinary drugs -> permethrin, combinations, Ectoparasiticides for topical use, incl. insecticides -> Veterinary pharmacotherapeutic group -> EMA Drug Category
Pharmaceuticals -> UK Veterinary Medicines Directorate List
S104 | UKVETMED | UK Veterinary Medicines Directorate's List | DOI:10.5281/zenodo.7802119

3.3.2 Endocrine Disruptors

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

3.3.3 Pesticides

Insecticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Pyrethrins/Pyrethroids
Pesticide
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Instrument Name
Bruker WH-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker WH-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 2
Technique
GC/MS
Source of Spectrum
H.H.Maurer, M.Meyer, K.Pfleger, A.A. Weber / University of Saarland, D-66424 Homburg Germany
Copyright
Copyright © 2023-2024 Wiley-VCH GmbH. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
GC/MS
Source of Spectrum
H.H.Maurer, M.Meyer, K.Pfleger, A.A. Weber / University of Saarland, D-66424 Homburg Germany
Copyright
Copyright © 2023-2024 Wiley-VCH GmbH. All Rights Reserved.
Thumbnail
Thumbnail

4.2.2 MS-MS

1 of 6
View All
Spectra ID
Instrument Type
LC-ESI-QFT
Ionization Mode
positive
Top 5 Peaks

149.0233 100

167.0338 46.13

71.0854 24.03

355.1093 5.54

183.0803 5.38

Thumbnail
Thumbnail
Notes
instrument=Q Exactive Orbitrap Thermo Scientific
2 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

149.0234 100

71.0855 6.30

57.0699 4.43

121.0284 4.26

168.057 2.06

Thumbnail
Thumbnail

4.2.3 LC-MS

1 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
15 (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
18.0 min
Precursor m/z
391.0862
Precursor Adduct
[M+H]+
Top 5 Peaks

149.0233 999

167.0338 460

71.0854 240

355.1093 55

183.0803 53

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
18.0 min
Precursor m/z
391.0862
Precursor Adduct
[M+H]+
Top 5 Peaks

149.0234 999

71.0855 119

167.0339 78

57.0699 43

183.0805 42

Thumbnail
Thumbnail
License
CC BY

4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
FILM (CAST FROM ACETONE)
Source of Sample
Riedel-De Haen AG
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Crescent Chemical Co.
Catalog Number
PS758
Lot Number
972100
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Crescent Chemical Co.
Catalog Number
PS758
Lot Number
972100
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5 Other Spectra

IR Spectrum, Mass Spectrum (electron ionization)
NIST; Chemistry WebBook. National Institute of Standards and Technology Standard Reference Database Number 69 - March 2003 Release, Available from the query page at https://webbook.nist.gov/chemistry

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For the treatment of infestation with Sarcoptes scabiei (scabies).
Treatment of flea infestations (Ctenocephalides felis); the product has persistent insecticidal efficacy for up to 4 weeks against Ctenocephalides felis. The product has persistent acaricidal efficacy for up to 5 weeks against Ixodes ricinus and up to 3 weeks against Rhipicephalus sanguineus. One treatment provides repellent (anti-feeding) activity against sand flies (Phlebotomus perniciosus) for up to 3 weeks. ,

7.2 Drug Classes

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antiparasitic Agents; Insecticides

7.3 WHO Essential Medicines

Drug
Drug Classes
Dermatological medicines &gt; Scabicides and pediculicides
Formulation
(1) Local - Topical - Lotion: 1%; (2) Local - Topical - Cream: 5%
Indication
(1) Pediculosis corporis; (2) Pediculosis capitis; (3) Scabies

7.4 FDA Approved Drugs

7.5 FDA Orange Book

7.6 FDA National Drug Code Directory

7.7 Drug Labels

Drug and label
Active ingredient and drug
Homeopathic product and label

7.8 Clinical Trials

7.8.1 ClinicalTrials.gov

7.8.2 EU Clinical Trials Register

7.9 EMA Drug Information

Category
Veterinary drugs
Active Substance
indoxacarb, permethrin
INN/Common name
indoxacarb, permethrin
Pharmacotherapeutic Classes
permethrin, combinations, Ectoparasiticides for topical use, incl. insecticides
Status
Withdrawn
Company
Intervet International BV
Market Date
2012-01-09

7.10 Therapeutic Uses

MEDICATION (VET)
Crusted (Norwegian) scabies, a rare variant of ordinary scabies, is a highly contagious infection in which the skin is infested with thousands to millions of mites. The infection is frequently overlooked because of its atypical presentations. Patients with cognitive deficiency or an immunodeficiency disorder (including immunosuppressive therapy) are predisposed to developing crusted scabies. The infection often presents as generalized dermatitis with crusted hyperkeratosis on the palms and soles. Diagnosis is made by examining skin scrapings from the crusted lesions. Lindane is the scabicide most widely used in the treatment of crusted scabies. Eradication frequently requires repeated applications, and care must be taken to avoid lindane toxicity. Permethrin cream is as efficacious as lindane in the treatment of ordinary scabies. Because of its wider margin of safety, permethrin may become the preferred treatment for crusted scabies.
Kolar KA, Rapini RP; Am Fam Physician 44 (4): 1317-21 (1991)
Permethrin is a synthetic pyrethroid that has low mammalian toxicity and an insecticidal effectiveness higher that of the natural pyrethrins. Because of its high ovicidal activity and persistence on hair, a properly applied 1% cream rinse preparation eliminates head lice infestation after a single application. Fewer than 1% of patients have required retreatment after seven days.
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1436
Permethrin exerts ovicidal effects against lice, and some activity may result from residues that remain on the hair for 2 weeks or longer that kill nymphs as they emerge from eggs.In one in vitro study using live lice and viable nits obtained from healthy lice-infested children in Panama, exposure to permethrin 1% cream rinse killed 30% of the lice within 5 minutes, 53% within 10 minutes, and 100% within 1 hour; 89% of the nits were killed within 10 minutes. However, when permethrin 1% was diluted 10:1 in water to approximate the dilution that occurs when the drug is applied to wet hair, 11% of the lice were killed within 5 minutes, 44% within 10 minutes, and 94% within 1 hour; 81% of the nits were killed within 10 minutes when exposed to the diluted solution.
American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 84:04.12
For more Therapeutic Uses (Complete) data for PERMETHRIN (19 total), please visit the HSDB record page.

7.11 Drug Warnings

The safety and effectiveness of permethrin in children less than 2 years of age have not been established.
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1436
Patients who cannot tolerate chrysanthemums, pyrethrins, and other synthetic pyrethroids may not tolerate permethrin.
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1436

8 Food Additives and Ingredients

8.1 Food Additive Classes

JECFA Functional Classes
Veterinary Drug -> INSECTICIDE;

8.2 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

Chemical Name
PERMETHRIN
Evaluation Year
2001
ADI
Not established
Comments
An ADI of 0-50 mg/kg bw for technical grade permethrin with cis:trans ratios of 25:75 to 40:60 was established by the 1999 Joint FAO/WHO Meeting on Pesticide Residues (JMPR; FAO Plant Production and Protection Paper 153, Rome, 2000). At its fifty-forth meeting (2000), the Committee was unable to establish an ADI for the 80:20 cis:trans isomeric mixture proposed for use as a veterinary drug because of the lack of information on toxicity and the fact that the cis-isomer is substantially more toxic than the trans isomer.

9 Agrochemical Information

9.1 Agrochemical Category

Insecticide
Pesticide active substances -> Insecticides

9.2 EU Pesticides Data

Active Substance
permethrin
Status
Not approved [Reg. (EC) No 1107/2009]
Legislation
00/817/EC

10 Pharmacology and Biochemistry

10.1 Pharmacodynamics

Permethrin, a pyrethroid, is active against a broad range of pests including lice, ticks, fleas, mites, and other arthropods.

10.2 MeSH Pharmacological Classification

Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
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.)

10.3 FDA Pharmacological Classification

1 of 3
Non-Proprietary Name
PERMETHRIN
Pharmacological Classes
Pyrethroid [EPC]; Pyrethrins [CS]
2 of 3
Non-Proprietary Name
PERMETHRIN 5% W/W
Pharmacological Classes
Pyrethroid [EPC]; Pyrethrins [CS]
3 of 3
Non-Proprietary Name
PERMETHRIN CREAM 5% W/W
Pharmacological Classes
Pyrethroid [EPC]; Pyrethrins [CS]

10.4 ATC Code

QP53AC54
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

P - Antiparasitic products, insecticides and repellents

P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents

P03A - Ectoparasiticides, incl. scabicides

P03AC - Pyrethrines, incl. synthetic compounds

P03AC04 - Permethrin

10.5 Absorption, Distribution and Excretion

Absorption
Poorly absorbed through the skin.
Route of Elimination
Permethrin is rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.
Lactating cows (three/group) fed permethrin at dose levels of 0, 0.2, 1.0, 10, 50 mg/kg diet for 28 days showed no mortality, and growth and milk production were normal. Permethrin residues were observed in the milk within 3 days at the two highest dietary levels; levels appeared to reach a plateau rapidly and not to increase with time. Analysis of individual cis and trans isomers showed that the ratio of permethrin isomers in milk appeared to change during the course of the study with the cis isomer predominating. Permethrin residues were not found in the tissues of animals that received doses of 1 mg/kg or less. At dose levels of 10 or 50 mg/kg, residues were detected in the tissues, predominantly in the fat. Low levels were also present in the muscle and kidney at the highest dose level. Permethrin did not appear to accumulate in the fat but to reach a plateau rapidly.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
(14)C-cis-Permethrin was applied to the clipped skin of mice at a level of 1 mg/kg body weight in 0.1 mL of acetone. The mice were restrained until the solvent had evaporated and then placed in mouse metabolism cages. They were sacrificed at 1, 5, 15, 50, 480, and 2880 min after treatment and examined for absorption, distribution, and excretion of the insecticide. About 40% of the applied permethrin had moved from the site of application within 5 min and appeared to move rapidly to other parts of the body.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
When ten consecutive oral doses of (14)C-trans- or (14)C-cis- permethrin (labelled in the acid or alcohol moieties) at 0.2-0.3 mg/kg bw/day were given to lactating goats, they excreted 72-79% and 25-36% of the trans and cis isomer doses, respectively, in urine & 12-15%, respectively, in the feces. The amounts of the radiocarbon appearing in the milk were <0.7% with any one of the four (14)C-labelled preparations. Concerning the tissue residues 24 hr after the last dose, detectable levels of radiocarbon were found in most tissue, but none was >0.04 mg/kg for the trans isomer or 0.25 mg/kg for the cis isomer.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
Two human volunteers, who consumed about 2 and 4 mg of permethrin (25:75), respectively, excreted 18-37% and 32-39% of the administered dose, detected as the metabolite Cl2CA, after acid hydrolysis of their urine collected over 24 hr.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
For more Absorption, Distribution and Excretion (Complete) data for PERMETHRIN (37 total), please visit the HSDB record page.

10.6 Metabolism / Metabolites

Rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.
When the four (14)C-preparations of (IRS)-trans-, (IR)-trans- , (IRS)-cis, and (IR)-cis-permethrin labeled in the alcohol and acid moieties were administered orally to male rats at 1.6-4.8 mg/kg, the compounds were rapidly metabolized and the (14)C from the acid and alcohol moeity was almost completely eliminated from the body within a few days. ... The major metabolic reactions of both permethrin isomers /(trans and cis)/ were oxidation at the trans and cis portions of the gem-dimethyl group of the acid moiety and at the 2'- and 4'-positions of the alcohol moiety, ester cleavage, and the conjugation of the resulting carboxylic acids, alcohols, and phenols with glucuronic acid, glycine, and sulfuric acid. The cis isomer is more stable than the tans isomer, and the cis isomer yielded four fecal ester metabolites which resulted from hydroxylation at the 2'- and 4'-positions of the phenoxy group, at the trans- methyl group, and at both of the two latter sites. The ester-cleaved metabolites were extensively excreted into the urine, whereas the metablites retaining ester linkage were found only in the feces. There were no significant differences in metabolism between the (IRS)-isomers and (IR)-isomers.
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1280
When White Leghorn hens were treated orally three consecutive days with one of four (14)C-trans- and cis-permethrin isomers labelled in the alcohol or acid at 10 mg/kg body weight, they showed no signs of poisoning. More than 87% of the radiocarbon from the four labelled perparations was found in the excreta 9 days after the initial dose, 0.7-4.7% of the dose was exhaled as (14)CO2, and 0.12-0.47% and 0.06-0.66% of the radiocarbon was recovered in egg yolk and fat (subcutaneous and visceral fat), respectively. Both the cis isomers labelled in the alcohol and acid moieties showed recoveries 3 to >10 times higher in the fat and egg yolk than those shown by the corresponding trans isomers. The excreta (0-72 hr) contained 1.7 times more cis-permethrin than trans-permethrin. Hydroxylated ester metabolites of trans-permethrin were not excreted, but four monohydroxy and dihydroxy esters (i.e. trans-OH-permethrin, 4'-OH-permethrin, 4'-OH, trans-OH-permethrin and trans-OH-permethrin sulfate) of cis-permethrin were found. Metabolites from the acid moieties of both isomers were the Cl2CA isomers in free, glucuronide, and taurine conjugate forms, trans-OH-Cl2CA, cis-OH-Cl2CA, cis-OH-Cl2CA lactone, and cis-OH-Cl2CA sulfate. trans-OH-Cl2CA was obtained from the cis isomer to larger extents than from the trans isomer, whereas the amounts of cis-OH-Cl2-CA were larger with the trans isomer than with the cis isomer. The metabolites from the alcohol moiety included PBalc, PBacid, their 4'-hydroxy-derivatives and the corresponding sulfate the glucuronide of PBalc, and a variety of unidentified conjugates of 4'-OH-PBalc and 4'-OH-PBacid. The taurine conjugate of PBacid was not detected. The metabolites produced in largest amounts were the unidentified conjugates of 4'-OH-PBalc (6-13% of the dose) and 4'-OH-PBacid (2-11%). The yolk of eggs 5 and 6 days after initial dosing contained 4.4 times cis-perethrin than trans-permethrin in unchanged form and the same ester metabolites of cis-permethrin as those found in the excreta. Other metabolites in the yolk were generally the same as those in the excreta. Overall, cis-permethrin appeared at higher levels than trans-permethrin in the egg yolk, fatty tissues, and excreta. Radiocarbon from cis-permethrin preparations also persisted longer in the blood than that from trans-permethrin preparations. It probably resulted from more rapid ester cleavage of the trans isomer than the cis isomer, based on the relative amounts of hydrolysis products form the two isomers in hen excreta.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
Two human volunteers, who consumed about 2 and 4 mg of permethrin (25:75), respectively, excreted 18-37% and 32-39% of the administered dose, detected as the metabolite Cl2CA, after acid hydrolysis of their urine collected over 24 hr.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
The permethrin metabolites in goats were formed through cleavage of the ester linkage, hydroxylation at the cis- or trans-methyl of the geminal dimethyl group, and hydroxylation at the 4'-position of the phenoxybenzyl moiety. Some of these metabolic products were further oxidized and/or conjugated with glycine, glutamic acid and glucuronic acid. The major compounds found in feces after dosing with cis-permethrin were unmetabolized parent compound 4'-OH-permethrin, trans-OH-permethrin, PBalc, cis-OH-cis-Cl2CA-lactone and eight unidentified ester metabolites. The feces of goats treated with the trans isomer contained large amounts of the parent compound (41-79% of the fecal (14)C and of PBalc (8-25%) and cis-OH-trans-Cl2CA-lactone. Also, three unidentified ester metabolites were found (8-23%). On the other hand, major urinary metabolites from the alcohol moiety of both isomers were PBacid-glycine (7-9% of the urinary (14)C) and r'-OH-PBacid-glycine (4-12%). PBalc, PBacid, 4'-OH-PBalc, 4'-OH-PBacid, PBacid-glutamic acid and 4'-OH-PBacid-glutamic acid were also identified as minor metabolites. The urine of goats treated with both isomers contained as major components, Cl2CA in the free form (2-4% of the urinary (14)C) and as a glucuronide (27-71%). Cl2CA-glucuronide was obtained to a larger extent with the trans isomer than with the cis isomer. Other major metabolites of the cis isomer were cis-OH-Cl2CA (33) (9-11%) and cis-OH-cis-Cl2CA-lactone (11-16%). trans-OH-Cl2CA was detected as a minor metabolite of both isomers. The milk of goats contained the parent compounds, PBacid-glycine, and 4'-OH-PBacide-glycine. On administration of the cis isomer, a large amount of the parent compund was excreted in the milk than in the case of the trans isomer. Comparatively, when the trans isomer was administered, PBacid-glycine was detected in the milk to a larger extent than with the cis isomer. Most of the radioactivity in the fat was attributed to the parent compound or ester metabolites such as trans-OH-permethrin and trans-OH-permethrin conjugate.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
For more Metabolism/Metabolites (Complete) data for PERMETHRIN (25 total), please visit the HSDB record page.
The proposed metabolic pathway for cis- and trans-permethrin are as follows. The five principle sites of metabolic attack in both permethrin isomers is ester cleavage, oxidation at the trans- and cis-methyl of the geminal dimethyl group of the acid moiety, and oxidation at 2'- and 4'- position of the phenoxy group. Conjugation of the resultant carboxylic acids, alcohols, and phenols with glucuronic acid, glycine, and sulfuric acid occurs to varying extent. cis-Permethrin is more stable then trans-permethrin, and the cis isomer yields four faecally excreted ester metabolites that results from hydroxylation at the 2'- or 4'-position of the phenoxy group or at the trans- or cis methyl group on the cyclopropane ring. The estercleaved metabolites are extensively excreted into the urine whereas the metabolites retaining an ester bond are found only in the feces. The major metabolite from the acid moiety of both isomers was Cl2CA in free (1-8%) and glucuronide (14-42%) forms. Other significant metabolites are trans-OH-Cl2CA (1-5%) and cis-OH-Cl2CA in the free (3-5%), lactone (0-4%) and glucuronide (1-2%) forms. On the other hand, the alcohol moiety released after cleavage of the ester bond of both isomers is converted mainly to the sulfate of 3-(4'-hydroxyphenoxy)benzoic acid (4'-OH-PBacid) (29-43% of the dose) and PBacid in the free (1-10%) and glucuronide (7-15%) forms. Other significant metabolites of the alcohol moiety are PBalc, PBacid-glycine and the sulfate of 3-(2'-hydroxyphenoxy) benzoic acid (2'-OH-PBacid). A study by Nakamura et al. proposed that permethrin was hydrolyzed by CES (carboxylesterase), then PBAlc formed was oxidized to PBAld, and further, PBAld was oxidized to PBAcid by the P450 system in rat liver microsomes. (A559, A256) Route of Elimination: Permethrin is rapidly metabolized by ester hydrolysis to inactive metabolites which are excreted primarily in the urine.
A256: Nakamura Y, Sugihara K, Sone T, Isobe M, Ohta S, Kitamura S: The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats. Toxicology. 2007 Jun 25;235(3):176-84. Epub 2007 Mar 19. PMID:17451859
A559: Vogel JS, Bullen EC, Teygong CL, Howard EW: Identification of the RLBP1 gene promoter. Invest Ophthalmol Vis Sci. 2007 Aug;48(8):3872-7. PMID:17652763

10.7 Biological Half-Life

The toxicokinetics of permethrin after single 460 mg/kg oral and 46 mg/kg intravenous doses were studied in male Sprague-Dawley rats. Serial blood samples after oral and intravenous dosage, and brain, medulla oblongata, sciatic nerve, and liver samples after oral administration were collected. Plasma, hypothalamus, cerebellum, frontal cortex, caudate putamen, hippocampus, medulla oblongata, sciatic nerve, and liver concentrations of permethrin and its metabolites, m-phenoxybenzyl alcohol and m-phenoxybenzoic acid, were determined by a high-performance liquid chromatographic assay. The permethrin plasma profile could be adequately described by a two-compartment open model. For permethrin, the elimination half-life (t1/2 beta) and the mean residence time from plasma were 8.67 and 11.19 hr after i.v. and 12.37 and 17.77 hr after /peroal/ administration. The total plasma clearance was not influenced by dose concentration or route and reached a value of 0.058 liter/hr. After the single oral dose, permethrin was absorbed slowly with a Tmax of 3.52 hr. The maximum plasma concentration was 49.46 micrograms/ml. The oral bioavailability of permethrin was found to be 60.69%. The plasma concentration-time data for permethrin metabolites as well as the tissue concentration-time data for permethrin and its metabolites after an oral dose of permethrin were found to fit a one-compartment open model. The elimination half-life (t1/2el) of permethrin was greater for the hippocampus, medulla oblongata, frontal cortex, and sciatic nerve (23.10, 22.36, 13.86, and 16.27 hr, respectively) than for plasma (t1/2 beta, 12.37 hr). The maximum amounts of permethrin in cerebellum, hippocampus, caudate putamen, frontal cortex, hypothalamus, and sciatic nerve were about 1.5, 2, 2, 2.7, 4.8, and 7.5 times higher than in plasma, respectively, indicating an accumulation of pyrethroid by nervous tissue itself. Nervous tissue accumulation of permethrin was also reflected by the area under the concentration curve ratios of tissue/plasma (1.16, 3.71, 1.57, 4.27, 3.48, and 8.77, respectively). The metabolites of permethrin, m-phenoxy-benzyl alcohol and m-phenoxybenzoic acid, were detected in plasma and in all selected tissues for 48 hr after dosing, suggesting that a combination of metabolism by the tissues and diffusion into it from the blood may be present.
Anadon A et al; Toxicol Appl Pharmacol 110 (1): 1-8 (1991)
In studies, the half-life of (+)-trans- and (+)-cis-permethrin applied to the leaf surface of bean plants was 7 and 9 days, respectively.
Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 483

10.8 Mechanism of Action

Permethrin acts on the nerve cell membrane to disrupt the sodium channel current by which the polarization of the membrane is regulated. Delayed repolarization and paralysis of the pests are the consequences of this disturbance.
Permethrin is pediculocidal by disrupting in sodium channel current in the louse's nerve cell membrane; this action causes delayed polarization of the membrane and paralysis of the insect.
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1436
Like natural pyrethrins, permethrin acts as a neurotoxin by depolarizing nerve cell membranes of parasites. The drug disrupts the sodium channel current by which membrane repolarization is regulated. Delayed repolarization results in paralysis of the nerves in the exoskeletal respiratory muscles of the parasite leading to death.
American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 84:04.12
The synthetic pyrethroids delay closure of the sodium channel, resulting in a sodium tail current that is characterized by a slow influx of sodium during the end of depolarization. Apparently the pyrethroid molecule holds the activation gate in the open position. Pyrethroids with an alpha-cyano group (e.g., fenvalerate) produce more prolonged sodium tail currents than do other pyrethroids (e.g., permethrin, bioresmethrin). The former group of pyrethroids causes more cutaneous sensations than the latter. /Synthetic pyrethroids/
Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 1081
Trans- and cis-permethrin were irradiated in sunlight and at gamma>290 nm in hexane, methanol, water and water acetone. Isomerization and ester cleavage occurred primarily. Observed products included monochloropermethrin and the monochlorovinyl acid from cleavage, 3-phenoxybenzyl 3,3-dimethylacrylate, 3-phenoxybenzaldehyde, 3-phenoxybenzoic acid, benzyl alcohol, benzaldehyde, 3-hydroxybenzyl alcohol, benzoic acid, 3-hydroxybenzoic acid, and 3-phenoxybenzyl alcohol.
Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 484
For more Mechanism of Action (Complete) data for PERMETHRIN (10 total), please visit the HSDB record page.

10.9 Human Metabolite Information

10.9.1 Cellular Locations

  • Extracellular
  • Membrane

10.10 Transformations

11 Use and Manufacturing

11.1 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
Used as an ectoparasiticide in humans and animals; [Merck Index] Used as a nematocide, acaricide, and insecticide; [Hawley]
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.
Hawley - Lewis RJ. _Hawley's Condensed Chemical Dictionary, _15th Ed. New York: John Wiley & Sons, 2007.
Industrial Processes with risk of exposure
Farming (Pesticides) [Category: Industry]
For permethrin (USEPA/OPP Pesticide Code: 109701) 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./
National Pesticide Information Retrieval System's Database on Permethrin (52645-53-1). Available from, as of January 24, 2014: https://npirspublic.ceris.purdue.edu/ppis/
The pyrethroids are the most widely used class of insecticides in wood preservation because of their broad-spectrum activity, high efficacy especially against wood boring beetle, and high resistance to leaching. /Synthetic pyrethroids/
Pommer E-H, Jaetsch T; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2014). NY, NY: John Wiley & Sons; Wood, Preservation. Online Posting Date: April 15, 2007.
Insecticide, seed treatment/protectant.
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 592
It has a potential application for forest protection and vector control for the control of noxious insects in the household and on cattle, for the control of body lice, and in mosquito nets.
WHO; Environmental Health Criteria 94: Permethrin p.21 (1990)
For more Uses (Complete) data for PERMETHRIN (12 total), please visit the HSDB record page.

Use (kg; approx.) in Germany (2009): >250

Consumption (g per capita; approx.) in Germany (2009): 0.00305

Calculated removal (%): 97.4

For the treatment of infestation with <i>Sarcoptes scabiei</i> (scabies). Pyrethroids are used as insecticides. (L857)
L857: ATSDR - Agency for Toxic Substances and Disease Registry (2003). Toxicological profile for pyrethrins and pyrethroids. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp155.html

11.1.1 Use Classification

Veterinary drugs -> permethrin, combinations, Ectoparasiticides for topical use, incl. insecticides -> Veterinary pharmacotherapeutic group -> EMA Drug Category
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Veterinary Drug -> INSECTICIDE; -> JECFA Functional Classes
Hazard Classes and Categories ->
INSECTICIDES

11.1.2 Household Products

California Safe Cosmetics Program (CSCP)

Cosmetics product ingredient: Permethrin (including cis- and trans-)

Source: Permethrin is a synthetic chemical used as a pesticide and insect repellent. It is used in agriculture, veterinary health, and medication. Permethrin may be added to lotions intended to treat scabies (a skin infection caused by mites), and to sprays and shampoos used for lice control.

Potential health impacts: People may be exposed to permethrin by inhalation, ingestion, or through skin contact. Studies of scabies patients have found that dermal absorption of permethrin is low, but permethrin application may cause skin irritation. Inhaling permethrin may cause headache, nasal and respiratory irritation, dizziness, and nausea or vomiting. Studies of mice fed permethrin found increased rates of benign lung and liver tumors. The U.S. Environmental Protection Agency (U.S. EPA) classifies permethrin as likely to be carcinogenic to humans when ingested.

Product count: 2

Household & Commercial/Institutional Products

Information on 256 consumer products that contain Permethrin in the following categories is provided:

• Commercial / Institutional

• Inside the Home

• Landscaping/Yard

• Personal Care

• Pesticides

• Pet Care

11.2 Methods of Manufacturing

Permethrin can be produced by condensation of 3-phenoxybenzyl alcohol with (1RS)-cis/trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid.
Muller F et al; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2014). NY, NY: John Wiley & Sons; Acaricides. Online Posting Date: July 15, 2009.
The starting acid is prepared by a variation of the conventional chrysanthemic acid synthesis using ethyldiazoacetate in which 1,1-dichloro-4-methyl-1,3-pentadiene is reacted with ethyldiazoacetate in the presence of a copper catalyst and the resulting ethyl (+,-)- cis,trans-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate hydrolysed to the free acid. The cis- and trans-isomers can be separated from one another by selective crystallization from n-hexane in which the cis-isomer is more soluble. The starting acid is then reacted with 3-phenoxybenzyl alcohol to give permethrin.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V53 332 (1991)
Preparation of the racemic mixture: T. Mizutani et al, German patent 2437882 (1975 to Sumitomo); F. Mori et al; German patent 2544150; eidem, United States of America patent 4113968 (1976, 1978, both to Kuraray).
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1336

11.3 Formulations / Preparations

Dust, emulsifiable concentrate, smokes, ULV /ultra low volume/, wettable powder.
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 592
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 592
Technical material is a mixture of ~60% trans- and 40% cis-isomers.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1337
Permethrin is typically a mixture of (+) cis and (+) trans esters ... in either a 40:60 or 25:75 ratio.
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V53 329 (1991)
For more Formulations/Preparations (Complete) data for PERMETHRIN (46 total), please visit the HSDB record page.

11.4 Consumption Patterns

In 1992, the estimated agricultural use of permethrin in the United States was about 1,055,097 pounds.
USGS; Pesticide 1992 Annual Use Map for Permethrin 52645-53-1). March 20, 1998. Available from, as of Jan 12, 2001: https://ca.water.usgs.gov/pnsp/use92/

11.5 General Manufacturing Information

The WHO Recommended Classification of Pesticides by Hazard identifies permethrin (technical grade) as Class II: moderately hazardous; Main Use: insecticide.
WHO International Programme on Chemical Safety; The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2009 p.30 (2010)
Synthetic pyrethroid insecticide. ... Of the four possible isomers, the (1R,trans)- and the (1R,cis)-isomers are the two esters primarily responsible for insecticidal activity.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1336
Permethrin was first registered and tolerances established in the United States in 1979 for use on cotton (April 29, 1979 44FR 24287). The registration was made conditional due to the need for additional toxicology data to fully evaluate carcinogenicity and the need for additional ecological effects data to fully evaluate aquatic risk. Laboratory studies indicated that permethrin was highly toxic to fish and aquatic invertebrates and the use on cotton was classified as Restricted Use pesticide (RUP). In making its decision to conditionally register the product, EPA considered the beneficial role of this compound in cotton pest management, the reduction of use of other cotton insecticides with known carcinogenic potentials, and the absence of suitable and sufficient supplies of alternatives for control of resistant insect strains.
USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Permethrin p.3 EPA 738-R-09-306 (May 2009). Available from, as of January 27, 2014: https://www.epa.gov/pesticides/reregistration/status.htm
Permethrin is a restricted use pesticide for crop and wide area applications (i.e. nurseries, sod farms) due to high toxicity to aquatic organisms. It is a general use pesticide for residential and industrial applications.
USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Permethrin p.5 EPA 738-R-09-306 (May 2009). Available from, as of January 27, 2014: https://www.epa.gov/pesticides/reregistration/status.htm
For more General Manufacturing Information (Complete) data for PERMETHRIN (7 total), please visit the HSDB record page.

12 Identification

12.1 Analytic Laboratory Methods

Method: Abraxis 500201; Procedure: immunoassay, magnetic particle; Analyte: permethrin; Matrix: water (groundwater, surface water, well water); Detection Limit: 0.75 ppb.
National Environmental Methods Index; Analytical, Test and Sampling Methods. Permethrin (52645-53-1). Available from, as of January 24, 2014: https://www.nemi.gov
Method: EPA-OW/OST 1699; Procedure: high resolution gas chromatography combined with high resolution mass spectrometry; Analyte: permethrin; Matrix: multi-media environmental samples; Detection Limit: not provided.
National Environmental Methods Index; Analytical, Test and Sampling Methods. Permethrin (52645-53-1). Available from, as of January 24, 2014: https://www.nemi.gov
Analytical methods for determining ... pyrethroids in environmenal samples.
Sample Matrix
Air
Analyte
Permethrin
Preparation Method
Air samples collected on filter paper or Tenax tubes; extract with acetone
Analytical Method
Gas chromatography/mass spectrometry
Sample Detection Limit
1 ng/cu m
Sample Matrix
Air (dust)
Analyte
Permethrin
Preparation Method
Dust samples are homogenized in a blender or food processor; extract with acetone
Analytical Method
Gas chromatography/mass spectrometry
Sample Detection Limit
50 ng/g
Sample Matrix
Fatty and non fatty foods
Analyte
Permethrin
Preparation Method
Dissolve fat in petroleum ether; extract with acetonitrile; dilute with water; cleanup on Florisil column; elute with a series of eluants - methylene chloride, hexane, and acetonitrile
Analytical Method
Gas liquid chromatography/electron capture detector
Sample Detection Limit
No data
Sample Matrix
Non-fatty foods
Analyte
Permethrin
Preparation Method
Extract with acetonitrile or acetonitrile/water mixture; dilute with water; extract with petroleum ether; cleanup on Florisil column; elute with petroleum ether/ethyl ether
Analytical Method
Gas chromatography/flame ionization detector
Sample Detection Limit
No data
Sample Matrix
Fruits, vegetables, grains
Analyte
Permethrin
Preparation Method
Homogenize in acetonitrile and filter; extract with hexane; wash with 4% NaCl; dry over anhydrous sodium sulfate; evaporate to dryness; redissolve in hexane; extract with acetonitrile; evaporate to dryness; redissolve in hexane; cleanup on Florisil column; elute with a mixture of petroleum ether and ethyl ether.
Analytical Method
Gas chromatography/electron capture detector
Sample Detection Limit
No data
U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Pyrethrins and Pyrethroids p.210 (September 2003) PB2004-100004. Available from, as of March 11, 2014: https://www.atsdr.cdc.gov/toxprofiles/index.asp
Residue and environmental analyses are performed using a gas chromatograph equipped with an electron capture detector (minimum detectable concentration of 0.005 mg/kg). Technical products are analyzed using a gas chromatograph with a flame ionization detector.
WHO; Environ Health Criteria 94: Permethrin (1990). Available from, as of January 27, 2014: https://www.inchem.org/pages/ehc.html
For more Analytic Laboratory Methods (Complete) data for PERMETHRIN (10 total), please visit the HSDB record page.

12.2 Clinical Laboratory Methods

Method: EPA-OW/OST 1699; Procedure: high resolution gas chromatography combined with high resolution mass spectrometry; Analyte: permethrin; Matrix: tissue; Detection Limit: not provided.
National Environmental Methods Index; Analytical, Test and Sampling Methods. Permethrin (52645-53-1). Available from, as of January 24, 2014: https://www.nemi.gov
Methods for the analysis of permethrin:
Sample Matrix
Milk, animal tissue
Sample Preparation
Extract with acetone:hexane (1:1); partition into dimethylformamide (in 1% aqueous sodium sulfate solution); back-extract into hexane; clean-up on activated Florisil column
Assay Procedure
Gas chromatography/ electron capture detection. Method is suitable for determining total permethrin or the individual cis- and trans-permethrin isomers.
Limit of Detection
0.01 ppm (mg/L or mg/kg)
Sample Matrix
Eggs
Sample Preparation
Extract with acetone/hexane (1:1); wash with 10% sodium chloride solu-tion; partition into dimethylformamide (in 1% aqueous sodium sulfate solution); back-extract into hexane; clean-up on activated Florisil column plus Merckogel or Fractosil
Assay Procedure
Gas chromatography/ electron capture detection. Method is suitable for determining total permethrin or the individual cis- and trans-permethrin isomers.
Limit of Detection
0.02 ppm (mg/kg), (0.01 ppm for isomers)
IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V53 332 (1991)
Analytical methods for determining ... pyrethroids in biological materials.
Sample Matrix
Plasma
Analyte
Permethrin
Preparation Method
Precipitation of proteins followed by liquid-liquid extraction
Analytical Method
Gas chromatography/electron capture detector
Sample Detection Limit
5 ug/L
Sample Matrix
Plasma, urine
Analyte
Permethrin
Preparation Method
Mix samples with 70% methanol; pour on to Sep-Pak C18 columns pretreated with chloroform, methanol, methanol/water, and water; wash with water; elute with chloroform; evaporate to dryness under stream of N2; redissolve in ethanol.
Analytical Method
Gas chromatography/flame ionization detector
Sample Detection Limit
2 mg/L
U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Pyrethrins and Pyrethroids p.207 (September 2003) PB2004-100004. Available from, as of March 11, 2014: https://www.atsdr.cdc.gov/toxprofiles/index.asp

13 Safety and Hazards

13.1 Hazards Identification

13.1.1 GHS Classification

1 of 4
View All
Note
Pictograms displayed are for 99.8% (531 of 532) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 0.2% (1 of 532) of reports.
Pictogram(s)
Irritant
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H302+H332 (11.8%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

H302 (99.8%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (88.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H332 (99.8%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H400 (99.6%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (99.8%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P362+P364, 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 532 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 1 of 532 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 18 notifications provided by 531 of 532 reports by companies with hazard statement code(s).

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.

13.1.2 Hazard Classes and Categories

Acute Tox. 4 (99.8%)

Skin Sens. 1 (88.9%)

Acute Tox. 4 (99.8%)

Aquatic Acute 1 (99.6%)

Aquatic Chronic 1 (99.8%)

Acute toxicity (Oral) - Category 4

Specific target organ toxicity - Single exposure - Category 2 (nervous system)

Hazardous to the aquatic environment (Acute) - Category 1

Hazardous to the aquatic environment (Long-term) - Category 1

13.1.3 Health Hazards

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or asphyxiation. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

13.1.4 Fire Hazards

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, Capacitor, asymmetric, be aware of possible short circuiting as this product is transported in a charged state. Polymeric beads, expandable (UN2211) may evolve flammable vapours. (ERG, 2024)

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

13.1.5 Hazards Summary

A skin, eye, and respiratory tract irritant; [ICSC] May be a skin sensitizer; [eChemPortal: ESIS] May cause irritation; May cause skin sensitization; Targets the CNS in high-dose animal studies; [MSDSonline] Rapidly metabolized; Does not accumulate in body; Causes hyperactivity and tremors in high-dose feeding studies of experimental animals; Exposed workers complain of skin and eye irritation; No skin sensitization in animal studies; [INCHEM PDS: Permethrin] See Imiprothrin.

13.1.6 Skin, Eye, and Respiratory Irritations

Mild irritant to skin and eyes.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1337
The chief effect from exposure ... is skin rash particularly on moist areas of the skin. ... May irritate the eyes. /Pyrethroids/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 1
Permethrin is classified as category III for eye irritation potential and category IV for dermal irritation potential.
USEPA; Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) for Permethrin (52645-53-1). EPA738-R-09-306 p. 9 (May 2009). Available from, as of January 31, 2014: https://www.epa.gov/pesticides/reregistration/status_page_b.htm
In rabbits, technical permethrin produced mild primary skin irritation following 24- hour application of 0.5 mL to intact and abraded skin and mild primary eye irritation (conjunctivitis) following ocular instillation of 0.1 mL without rinsing.
International Program on Chemical Safety/Commission of the European Union; Data Sheets of Pesticides No. 51 Permethrin (VBC/DS/84.51). Available from, as of february, 2014: https://www.inchem.org/pages/pds.html

13.2 First Aid Measures

Inhalation First Aid
Fresh air, rest.
Skin First Aid
Remove contaminated clothes. 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. Refer for medical attention .

13.2.1 First Aid

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Refer to the "General First Aid" section. (ERG, 2024)

13.3 Fire Fighting

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

CAUTION: Fire involving Safety devices (UN3268) and Fire suppressant dispersing devices (UN3559) may have a delayed activation and a risk of hazardous projectiles. Extinguish the fire at a safe distance.

SMALL FIRE: Dry chemical, CO2, water spray or regular foam.

LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.

FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

13.4 Accidental Release Measures

13.4.1 Isolation and Evacuation

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

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)

13.4.2 Spillage Disposal

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT wash away into sewer. 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.

13.4.3 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

13.4.4 Preventive Measures

Avoid contact with eyes, skin, or clothing. Avoid breathing vapor or spray mist. Wash thoroughly after handling.
Crop Protection Handbook Volume 99, Meister Media Worldwide, Willoughby, OH 2013, p. 593
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Mixing /of permethrin/, if not mechanical, should always be carried out with a paddle of appropriate length. Avoid contact with mouth and eyes. Before eating, drinking or smoking, hands and other exposed skin should be thoroughly washed with alkaline soap.
International Program on Chemical Safety/Commission of the European Union; Data Sheets of Pesticides No. 51 Permethrin (VBC/DS/84.51). Available from, as of february, 2014: https://www.inchem.org/pages/pds.html

13.5 Handling and Storage

13.5.1 Nonfire Spill Response

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. For Asbestos, avoid inhalation of dust. Cover spill with plastic sheet or tarp to minimize spreading. Do not clean up or dispose of, except under supervision of a specialist.

SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area.

SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal.

LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2024)

13.5.2 Safe Storage

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.

13.6 Exposure Control and Personal Protection

13.6.1 Inhalation Risk

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

13.6.2 Effects of Short Term Exposure

The substance is irritating to the eyes, skin and respiratory tract.

13.6.3 Acceptable Daily Intakes

OPP RfD= 0.05 mg/kg; EPA RfD= 0.05 mg/kg;
USEPA/OPP; Health Effects Div RfD/ADI Tracking Report p.44 (8/26/91)
FAO/WHO ADI: 0.05 mg/kg bw
FAO/WHO; Pesticide Residues in Food - 1991. Joint Meeting of the FAO Panel of Experts on Pesticide Residues in Food and the Environment and the WHO Expert Group on Pesticide Residues. Geneva, September 16-22, 1991. Evaluations Part 1 - Residues. p.639 FAO Plant & Prod Protect Paper 113/1 (1992)

13.6.4 Allowable Tolerances

Tolerances are established for the combined residues of the insecticide cis- and trans-permethrin isomers [cis-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate] and [trans-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate] in/on the following food commodities:
Commodity
Alfalfa, forage
Parts per million
20
Commodity
Alfalfa, hay
Parts per million
45
Commodity
Almond
Parts per million
0.05
Commodity
Almond, hulls
Parts per million
20
Commodity
Artichoke, globe
Parts per million
5.0
Commodity
Asparagus
Parts per million
2.0
Commodity
Avocado
Parts per million
1.0
Commodity
Broccoli
Parts per million
2.0
Commodity
Brussels sprouts
Parts per million
1.0
Commodity
Cabbage
Parts per million
6.0
Commodity
Cattle, fat
Parts per million
1.5
Commodity
Cattle, meat
Parts per million
0.10
Commodity
Cattle, meat byproducts
Parts per million
0.10
Commodity
Cauliflower
Parts per million
0.5
Commodity
Cherry, sweet
Parts per million
4.0
Commodity
Cherry, tart
Parts per million
4.0
Commodity
Corn, field, forage
Parts per million
50
Commodity
Corn, field, grain
Parts per million
0.05
Commodity
Corn, field, stover
Parts per million
30
Commodity
Corn, pop, grain
Parts per million
0.05
Commodity
Corn, pop, stover
Parts per million
30
Commodity
Corn, sweet, forage
Parts per million
50
Commodity
Corn, sweet, kernel plus cob with husks removed
Parts per million
0.10
Commodity
Corn, sweet, stover
Parts per million
30
Commodity
Egg
Parts per million
0.10
Commodity
Eggplant
Parts per million
0.50
Commodity
Fruit, pome, group 11
Parts per million
0.05
Commodity
Garlic, bulb
Parts per million
0.10
Commodity
Grain, aspirated fractions
Parts per million
0.50
Commodity
Goat, fat
Parts per million
1.5
Commodity
Goat, meat
Parts per million
0.10
Commodity
Goat, meat byproducts
Parts per million
0.10
Commodity
Hazelnut
Parts per million
0.05
Commodity
Hog, fat
Parts per million
0.05
Commodity
Hog, meat
Parts per million
0.05
Commodity
Hog, meat byproducts
Parts per million
0.05
Commodity
Horse, fat
Parts per million
1.5
Commodity
Horse, meat
Parts per million
0.10
Commodity
Horse, meat byproducts
Parts per million
0.10
Commodity
Horseradish
Parts per million
0.50
Commodity
Kiwifruit
Parts per million
2.0
Commodity
Leaf petioles subgroup 4B
Parts per million
5.0
Commodity
Leafy greens subgroup 4A
Parts per million
20
Commodity
Lettuce, head
Parts per million
20
Commodity
Milk, fat (reflecting 0.88 ppm in whole milk)
Parts per million
3.0
Commodity
Mushroom
Parts per million
5.0
Commodity
Onion, bulb
Parts per million
0.10
Commodity
Peach
Parts per million
1.0
Commodity
Pepper, bell
Parts per million
0.50
Commodity
Pistachio
Parts per million
0.10
Commodity
Potato
Parts per million
0.05
Commodity
Poultry, fat
Parts per million
0.15
Commodity
Poultry, meat
Parts per million
0.05
Commodity
Poultry, meat byproducts
Parts per million
0.05
Commodity
Sheep, fat
Parts per million
1.5
Commodity
Sheep, meat
Parts per million
0.10
Commodity
Sheep, meat byproducts
Parts per million
0.10
Commodity
Soybean, seed
Parts per million
0.05
Commodity
Spinach
Parts per million
20
Commodity
Tomato
Parts per million
2.0
Commodity
Vegetable, cucurbit, group 9
Parts per million
1.5
Commodity
Walnut
Parts per million
0.05
Commodity
Watercress
Parts per million
5.0
40 CFR 180.378(a) (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of January 24, 2014: https://www.ecfr.gov/cgi-bin/ECFR?page=browse
Tolerances with regional registration, as defined in section 180.1(l) are established for the combined residues of the insecticide cis- and trans-permethrin isomers [cis-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate] and [trans-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate] in/on the following food commodities:
Commodity
Collards
Parts permillion
15
Commodity
Grass, forage
Parts permillion
15
Commodity
Grass, hay
Parts permillion
15
Commodity
Papaya
Parts permillion
1.0
Commodity
Turnip, tops
Parts permillion
10
Commodity
Turnip, roots
Parts permillion
0.20
40 CFR 180.378(c) (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of January 24, 2014: https://www.ecfr.gov/cgi-bin/ECFR?page=browse

13.6.5 Personal Protective Equipment (PPE)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024)

Employees should be provided with and required to use dust- and splash-proof safety goggles where /pyrethroids/ ... may contact the eyes. /Pyrethroids/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 3
Employees should be provided with and be required to use impervious clothing, gloves, and face shields (eight-inch minimum). /Pyrethroids/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 2
the /Environmental Protection/ Agency believes that double layer PPE /(Personal Protective Equipment)/ (coveralls over long pants and long sleeved shirt with socks and shoes) with chemical-resistant gloves will be protective because the dermal exposure an individual will receive from using a cold fogger is likely equivalent to the dermal exposure he/she will receive when applying a liquid-based spray of permethrin via any high pressure handheld application method.
USEPA; Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) for Permethrin (52645-53-1). EPA738-R-09-306 p. 76 (May 2009). Available from, as of January 31, 2014: https://www.epa.gov/pesticides/reregistration/status_page_b.htm
The /Environmental Protection/ Agency believes that based on the non-cancer and cancer risk estimates for occupational handlers using the liquid formulation of permethrin for agricultural crop uses, which involve much higher volume of product, baseline PPE /(Personal Protective Equipment)/ and chemical-resistant gloves will be adequately protective for all dip applications as well. However, to reduce additional exposure that may result from potential splashing of the product onto the individual during the dip application, the Agency is additionally requiring chemical-resistant aprons to be worn for animal use.
USEPA; Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) for Permethrin (52645-53-1). EPA738-R-09-306 p. 76 (May 2009). Available from, as of January 31, 2014: https://www.epa.gov/pesticides/reregistration/status_page_b.htm
For more Personal Protective Equipment (PPE) (Complete) data for PERMETHRIN (10 total), please visit the HSDB record page.

13.6.6 Preventions

Fire Prevention
NO open flames.
Exposure Prevention
PREVENT DISPERSION OF DUST!
Inhalation Prevention
Use ventilation, local exhaust or breathing protection.
Skin Prevention
Protective gloves. Protective clothing.
Eye Prevention
Wear face shield.
Ingestion Prevention
Do not eat, drink, or smoke during work. Wash hands before eating.

13.7 Stability and Reactivity

13.7.1 Air and Water Reactions

Insoluble in water.

13.7.2 Reactive Group

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

Ethers

Halogenated Organic Compounds

Hydrocarbons, Aliphatic Unsaturated

13.7.3 Reactivity Profile

A pyrethroid derivative.

13.8 Transport Information

13.8.1 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. /Pyrethroid pesticide, liquid, flammable, poisonous;Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid 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. /Pyrethroid pesticide, liquid, flammable, poisonous;Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid 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. /Pyrethroid pesticide, liquid, flammable, poisonous;Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid 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. /Pyrethroid pesticide, liquid, flammable, poisonous;Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid 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 PERMETHRIN (16 total), please visit the HSDB record page.

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

UN 3349; Pyrethroid pesticide, solid, toxic
UN 3350; Pyrethroid pesticide, liquid, flammable, toxic, flash point less than 23 degrees C
UN 3351; Pyrethroid pesticide, liquid, toxic, flammable, flash point not less than 23 degree C
UN 3352; Pyrethroid pesticide, liquid, toxic
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for PERMETHRIN (6 total), please visit the HSDB record page.

13.8.3 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 February 13, 2014: 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. /Pyrethroid pesticide, liquid, flammable, toxic, flash point less than 23 °C; Pyrethroid pesticide, liquid, toxic; Pyrethroid pesticide, liquid, toxic, flammable, flash point not less than 23 °C; Pyrethroid pesticide, solid toxic/
International Air Transport Association. Dangerous Goods Regulations. 47th Edition. Montreal, Quebec Canada. 2006., p. 244
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. /Pyrethroid pesticide, liquid, flammable, toxic, flash point less than 23 °C; Pyrethroid pesticide, liquid, toxic; Pyrethroid pesticide, liquid, toxic, flammable, flash point not less than 23 °C; Pyrethroid pesticide, solid toxic/
International Maritime Organization. IMDG Code. International Maritime Dangerous Goods Code Volume 2 2006, p. 175, 176
Should be transported and stored in clearly labelled, leakproof containers out of reach of children, away from food and drink. Avoid contact with metals other than aluminium and tin.
International Program on Chemical Safety/Commission of the European Union; Data Sheets of Pesticides No. 51 Permethrin (VBC/DS/84.51). Available from, as of february, 2014: https://www.inchem.org/pages/pds.html

13.8.4 DOT Label

Class 9

13.8.5 Packaging and Labelling

Do not transport with food and feedstuffs.

13.8.6 EC Classification

Symbol: Xn, N; R: 20/22-43-50/53; S: (2)-13-24-36/37/39-60-61

13.8.7 UN Classification

UN Hazard Class: 6.1; UN Pack Group: III

13.9 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
Status Regulation (EC)
00/817/EC
New Zealand EPA Inventory of Chemical Status
Permethrin: HSNO Approval: HSR003111 Approved with controls

13.9.1 State Drinking Water Guidelines

(FL) FLORIDA 350 ug/L
USEPA/Office of Water; Federal-State Toxicology and Risk Analysis Committee (FSTRAC). Summary of State and Federal Drinking Water Standards and Guidelines (11/93) To Present

13.9.2 FIFRA Requirements

Tolerances are established for the combined residues of the insecticide cis- and trans-permethrin isomers [cis-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate] and [trans-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate] in/on the following food commodities:
Commodity
Alfalfa, forage
Commodity
Alfalfa, hay
Commodity
Almond
Commodity
Almond, hulls
Commodity
Artichoke, globe
Commodity
Asparagus
Commodity
Avocado
Commodity
Broccoli
Commodity
Brussels sprouts
Commodity
Cabbage
Commodity
Cattle, fat
Commodity
Cattle, meat
Commodity
Cattle, meat byproducts
Commodity
Cauliflower
Commodity
Cherry, sweet
Commodity
Cherry, tart
Commodity
Corn, field, forage
Commodity
Corn, field, grain
Commodity
Corn, field, stover
Commodity
Corn, pop, grain
Commodity
Corn, pop, stover
Commodity
Corn, sweet, forage
Commodity
Corn, sweet, kernel plus cob with husks removed
Commodity
Corn, sweet, stover
Commodity
Egg
Commodity
Eggplant
Commodity
Fruit, pome, group 11
Commodity
Garlic, bulb
Commodity
Grain, aspirated fractions
Commodity
Goat, fat
Commodity
Goat, meat
Commodity
Goat, meat byproducts
Commodity
Hazelnut
Commodity
Hog, fat
Commodity
Hog, meat
Commodity
Hog, meat byproducts
Commodity
Horse, fat
Commodity
Horse, meat
Commodity
Horse, meat byproducts
Commodity
Horseradish
Commodity
Kiwifruit
Commodity
Leaf petioles subgroup 4B
Commodity
Leafy greens subgroup 4A
Commodity
Lettuce, head
Commodity
Milk, fat (reflecting 0.88 ppm in whole milk)
Commodity
Mushroom
Commodity
Onion, bulb
Commodity
Peach
Commodity
Pepper, bell
Commodity
Pistachio
Commodity
Potato
Commodity
Poultry, fat
Commodity
Poultry, meat
Commodity
Poultry, meat byproducts
Commodity
Sheep, fat
Commodity
Sheep, meat
Commodity
Sheep, meat byproducts
Commodity
Soybean, seed
Commodity
Spinach
Commodity
Tomato
Commodity
Vegetable, cucurbit, group 9
Commodity
Walnut
Commodity
Watercress
40 CFR 180.378(a) (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of January 24, 2014: https://www.ecfr.gov/cgi-bin/ECFR?page=browse
Tolerances with regional registration, as defined in section 180.1(l) are established for the combined residues of the insecticide cis- and trans-permethrin isomers [cis-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate] and [trans-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate] in/on the following food commodities:
Commodity
Collards
Commodity
Grass, forage
Commodity
Grass, hay
Commodity
Papaya
Commodity
Turnip, tops
Commodity
Turnip, roots
40 CFR 180.378(c) (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of January 24, 2014: https://www.ecfr.gov/cgi-bin/ECFR?page=browse
The Agency has completed its assessment of the dietary, occupational, residential, and ecological risk associated with the use of pesticide products containing the active ingredient permethrin. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient permethrin, the Agency has sufficient information on the human health and ecological effects to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that permethrin-containing products are eligible for reregistration provided that: (i) the risk mitigation measures outlined in this document are adopted and (ii) label amendments are made to reflect these measures. ... Based on its evaluation of permethrin, the Agency has determined that permethrin products, unless labeled and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the risk mitigation measures identified in this document, the Agency may take regulatory action to address the risk concerns from the use of permethrin. If all changes outlined in this document are incorporated into the product labels, then all current risks for permethrin will be adequately mitigated for the purposes of this determination under FIFRA.
USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Permethrin p.57 EPA 738-R-09-306 (May 2009). Available from, as of January 27, 2014: https://www.epa.gov/pesticides/reregistration/status.htm
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Permethrin is found on List B. Case No: 2510; Pesticide type: Insecticide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 3-(Phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; Data Call-in (DCI) Date(s): 08/09/91, 01/02/92, 04/11/94, 03/03/95, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
United States Environmental Protection Agency/ Prevention, Pesticides and Toxic Substances; Status of Pesticides in Registration, Reregistration, and Special Review. (1998) EPA 738-R-98-002, p. 198

13.9.3 FDA Requirements

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including permethrin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
DHHS/FDA; Electronic Orange Book-Approved Drug Products with Therapeutic Equivalence Evaluations. Available from, as of January 27, 2014: https://www.fda.gov/cder/ob/

13.10 Other Safety Information

13.10.1 History and Incidents

An outbreak of typhoid fever in rural Malawi triggered an investigation by the Malawi Ministry of Health and the Centers for Disease Control and Prevention in July 2009. During the investigation, villagers were directly consuming washed, donated, pesticide-treated wheat seed meant for planting. The objective of this study was to evaluate the potential for pesticide exposure and health risk in the outbreak community. A sample of unwashed (1430 g) and washed (759 g) wheat seed donated for planting, but which would have been directly consumed, was tested for 365 pesticides. Results were compared with each other (percentage change), the US Environmental Protection Agency's (EPA) health guidance values and estimated daily exposures were compared with their Reference dose (RfD). Unwashed and washed seed samples contained, respectively: carboxin, 244 and 57 / parts per billion / (ppm); pirimiphos methyl, 8.18 and 8.56 ppm; total permethrin, 3.62 and 3.27 ppm; and carbaryl, 0.057 and 0.025ppm. Percentage change calculations (unwashed to washed) were as follows: carboxin, -76.6%; pirimiphos methyl, +4.6%; total permethrin, -9.7%; and carbaryl -56.1%. Only carboxin and total permethrin concentration among washed seed samples exceeded US EPA health guidance values (285 x and seven times, respectively). Adult estimated exposure scenarios (1 kg seed) exceeded the RfD for carboxin (8 x ) and pirimiphos methyl (12 x ). Adult villagers weighing 70 kg would have to consume 0.123, 0.082, 1.06, and 280 kg of washed seed daily to exceed the RfD for carboxin, pirimiphos methyl, permethrins, and carbaryl, respectively. Carboxin, pirimiphos methyl, permethrins, and carbaryl were detected in both unwashed and washed samples of seed. Carboxin, total permethrin, and carbaryl concentration were partially reduced by washing. Health risks from chronic exposure to carboxin and pirimiphos methyl in these amounts are unclear. The extent of this practice among food insecure communities receiving relief seeds and resultant health impact needs further study.
Schier JG et al; J Expo Sci Environ Epidemiol 22 (6): 569-73 (2012)

13.10.2 Special Reports

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Permethrin EPA 738-R-09-306 (May 2009). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of January 27, 2014: http://www.epa.gov/pesticides/reregistration/status.htm]
U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Pyrethrins and Pyrethroids (September 2003) PB2004-100004). The ATSDR toxicological profile succinctly characterizes the toxicologic and adverse health effects information for the hazardous substance described here. Each peer-reviewed profile identifies and reviews the key literature that describes a hazardous substance's toxicologic properties. Other pertinent literature is also presented, but is described in less detail than the key studies.[Available from, as of March 11, 2014: http://www.atsdr.cdc.gov/toxprofiles/index.asp]
Clark JR et al; Toxicity of Pyrethroids to Marine Invertebrates and Fish: A Literature Review and Test Results with Sediment-Sorbed Chemicals. Environ Toxicol Chem 8 (5): 393-401 (1989). Data on acute and chronic toxicity of permethrin, fenvalerate, cypermethrin, and flucythinate to marine invertebrates and fishes are reviewed.
Mian LS, Mulla MS; Effects of Pyrethroid Insecticides on Nontarget Invertebratesin Aquatic Ecosystems. J Agric Entomol 9 (2): 73-98 (1992). This review presents data on the impacts of pyrethroid insecticides on nontarget aquatic invertebrates.
For more Special Reports (Complete) data for PERMETHRIN (10 total), please visit the HSDB record page.

14 Toxicity

14.1 Toxicological Information

14.1.1 Toxicity Summary

Pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. (T18, L857)
L857: ATSDR - Agency for Toxic Substances and Disease Registry (2003). Toxicological profile for pyrethrins and pyrethroids. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp155.html
T18: Hayes WJ Jr. and Laws ER Jr. (eds) (1991). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc.

14.1.2 EPA IRIS Information

Substance
Toxicity Summary
EPA IRIS Summary PDF (Update: Mar-31-1987 )
Critical Effect Systems
Hepatic
Reference Dose (RfD), chronic
5 x 10 ^-2 mg/kg-day

14.1.3 RAIS Toxicity Values

Oral Acute Reference Dose (RfDoa)(mg/kg-day)
0.44
Oral Acute Reference Dose Reference
OPP
Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.05
Oral Chronic Reference Dose Reference
IRIS Current
Oral Subchronic Chronic Reference Dose (RfDos) (mg/kg-day)
0.2
Oral Subchronic Chronic Reference Dose Reference
ATSDR Final
Short-term Oral Reference Dose (RfDot) (mg/kg-day)
0.2
Short-term Oral Reference Dose Reference
ATSDR Final

14.1.4 EPA Human Health Benchmarks for Pesticides

Chemical Substance
Acute or One Day PAD (RfD) [mg/kg/day]
0.44
Acute or One Day HHBPs [ppb]
2900
Acute HHBP Sensitive Lifestage/Population
Children

14.1.5 USGS Health-Based Screening Levels for Evaluating Water-Quality

Chemical
Permethrin
Chemical Classes
Pesticide
Chronic Noncancer HHBP (Human Health Benchmarks for Pesticides)[μg/L]
2900
Benchmark Remarks
Acute HHBP for children; the acute PAD adequately accounts for all chronic toxicity, including carcinogenicity
Reference
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

14.1.6 Evidence for Carcinogenicity

The /Environmental Protection/ Agency classified permethrin as "Likely to be Carcinogenic to Humans" by the oral route. This classification was based on two reproducible benign tumor types (lung and liver) in the mouse, equivocal evidence of carcinogenicity in Long-Evans rats, and supporting structural activity relationships (SAR) information. For the purpose of risk characterization, a low dose extrapolation model (Q1*) was used. The Q1* is 9.6 x 10-3 (mg/kg/day)-1 and was derived from the female mouse lung (adenoma and/or carcinoma) tumors
USEPA; Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) for Permethrin (52645-53-1). EPA738-R-09-306 p. 12 (May 2009). Available from, as of January 31, 2014: https://www.epa.gov/pesticides/reregistration/status_page_b.htm

14.1.7 Carcinogen Classification

1 of 2
IARC Carcinogenic Agent
Permethrin
IARC Carcinogenic Classes
Group 3: Not classifiable as to its carcinogenicity to humans
IARC Monographs
Volume 53: (1991) Occupational Exposures in Insecticide Application, and Some Pesticides
2 of 2
Carcinogen Classification
3, not classifiable as to its carcinogenicity to humans. (L135)

14.1.8 Health Effects

As for every type I pyrethroids , permethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis can also occur following permethrin poisoning. (L857)
L857: ATSDR - Agency for Toxic Substances and Disease Registry (2003). Toxicological profile for pyrethrins and pyrethroids. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp155.html

14.1.9 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Because less than 2% is absorbed after topical application, rapid metabolism to inactive metabolites and safe application directly on infants' skin, topical permethrin products are acceptable in nursing mothers. Extensive exposure, such as from agricultural use or malaria control might have long-term health concerns because residues can be found in breastmilk. Only water-miscible cream, gel or liquid products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.

◉ Effects in Breastfed Infants

In a telephone follow-up study, 5 mothers who used permethrin during breastfeeding reported no adverse reactions in their breastfed infants.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

14.1.10 Exposure Routes

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857). Poorly absorbed through the skin.
L857: ATSDR - Agency for Toxic Substances and Disease Registry (2003). Toxicological profile for pyrethrins and pyrethroids. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp155.html

14.1.11 Symptoms

Inhalation Exposure
Cough.
Skin Exposure
Redness. Burning sensation.
Eye Exposure
Redness. Pain.
Ingestion Exposure
Burning sensation. Diarrhoea. Vomiting.
Following oral exposure, severe fine tremor, marked reflex hyperexcitability, sympathetic activation can occur. Nausea, vomiting and abdominal pain commonly occur and develop following ingestion. Sudden bronchospasm, swelling of oral and laryngeal mucous membranes, and anaphylactoid reactions have been reported after inhalation. Hypersensitivity reactions characterized by pneumonitis, cough, dyspnea, wheezing, chest pain, and bronchospasm may occur too . Dermatitis is the main effect of a dermal exposure to permethrin. (T36)
T36: Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.

14.1.12 Target Organs

Hepatic

14.1.14 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.

14.1.15 Acute Effects

14.1.16 Toxicity Data

LC50 (rat) = 485 mg/m3
Oral, rat LD<sub>50</sub>: 430 - 4000 mg/kg Skin, rabbit LD<sub>50</sub>: 2000 mg/kg LD50: 3 801 mg/kg (Oral, Rat) (L857)
L857: ATSDR - Agency for Toxic Substances and Disease Registry (2003). Toxicological profile for pyrethrins and pyrethroids. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp155.html

14.1.17 Minimum Risk Level

Intermediate Oral: 0.2 mg/kg/day (Rat) (L857)
L857: ATSDR - Agency for Toxic Substances and Disease Registry (2003). Toxicological profile for pyrethrins and pyrethroids. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp155.html

14.1.18 Treatment

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (T36)
T36: Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.

14.1.19 Interactions

The effects of pyrethroids were studied on phosphoinositide breakdown in guinea pig synaptoneurosomes. Similar to other agents that activate voltage-dependent sodium channels, type I and type II pyrethroids stimulated phosphoinositide breakdown. Type II pyrethroids, like deltamethrin and fenvalerate, were more potent and, at least for deltamethrin, more efficacious than type I pyrethroids, like allethrin, resmethrin and permethrin. The effects of type II pyrethroids could be partially inhibited by the sodium channel blocker tetrodotoxin. The effects of allethrin and resmethrin were not affected by 5 microM tetrodotoxin. Stimulation of phosphoinositide breakdown by fenvalerate was additive to the stimulation elicited by the receptor agonists carbamylcholine and norepinephrine, but not to the stimulation elicited by sodium channel agents (batrachotoxin, scorpion venom and pumiliotoxin B). Stimulation by allethrin was not additive to the stimulation elicited either by receptor agonists or sodium channel agents. A submaximal concentration of allethrin, a type I pyrethroid, did not greatly affect the dose-dependent stimulation elicited by a type II pyrethroid, deltamethrin, while a higher concentration of allethrin prevented further stimulation by type II pyrethroids. A local anesthetic, dibucaine, which inhibits sodium channel activation, inhibited phosphoinositide breakdown induced by type II, but not by type I pyrethroids, except at higher concentrations. Thus, type II pyrethroids appear to stimulate phosphoinositide breakdown in synaptoneurosomes in a manner analogous to other sodium channel agents, while type I pyrethroids elicit phosphoinositide breakdown by a different mechanism, probably not involving sodium channels.
Gusovsky F et al; Brain Res. 492(1-2): 72-8 (1989)
/Pyrethroid/ detoxification ... important in flies, may be delayed by the addition of synergists ... organophosphates or carbamates ... to guarantee a lethal effect. ... /Pyrethroid/
Buchel KH (ed); Chemistry of Pesticides p.19 (1983)
Piperonyl butoxide potentiates /insecticidal activity/ of pyrethrins by inhibiting the hydrolytic enzymes responsible for pyrethrins' metabolism in arthropods. When piperonyl butoxide is combined with pyrethrins, the insecticidal activity of the latter drug is increased 2-12 times /Pyrethrins/
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2000.Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2000 (Plus Supplements)., p. 3203
At dietary level of 1000 ppm pyrethrins and 10000 ppm piperonyl butoxide ... /enlargement, margination, and cytoplasmic inclusions in liver cells of rats/ were well developed in only 8 days, but ... were not maximal. Changes were proportional to dosage and similar to those produced by DDT. Effects of the 2 ... were additive. /Pyrethrins/
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 78
/Nuclear magnetic resonance/ (NMR) combined with pattern recognition was recently introduced as a new technique for rapid xenobiotic toxicity evaluation. In this article, metabolic changes in the biofluid of rats after 90-day oral treatment with propoxur, permethrin and a combination of these two pesticides were investigated. Propoxur dosing induced increased urinary taurine, creatinine and glucose, whereas urinary lactate and acetate were increased in the highest permethrin dose group. Urinary acetate, alanine, lactate and trimethylamine levels were increased in the mixture group, accompanied by decreased urinary tricarboxylic acid cycle intermediates. In addition, the highest dose of the mixture displayed raised 3-D-hydroxybutyrate, acetate and lactate levels in the serum sample. Chronic exposure to a combination of propoxur and permethrin may induce hepatotoxicity and nephrotoxicity. An increase in acetate, alanine and formate in the urine could be a potentially sensitive biomarker of the chronic, combined effects of permethrin and propoxur.
Liang YJ et al; Bioanalysis 4 (24): 2897-907 (2012)

14.1.20 Antidote and Emergency Treatment

Skin decontamination. Wash skin promptly with soap and water ... . If irritant or paresthetic effects occur, obtain treatment by a physician. Because volatilization of pyrethroids apparently accounts for paresthesia affecting the face, strenuous measures should be taken (ventilation, protective face mask and hood) to avoid vapor contact with the face and eyes. Vitamin E oil preparations (dL-alpha tocopheryl acetate) are uniquely effective in preventing and stopping the paresthetic reaction. They are safe for application to the skin under field conditions. Corn oil is somewhat effective, but possible side effects with continuing use make it less suitable. Vaseline is less effective than corn oil. Zinc oxide actually worsens the reaction. /Pyrethroids/
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. 88
Eye contamination. Some pyrethroid compounds can be very corrosive to the eyes. Extraordinary measures should be taken to avoid eye contamination. the eye should be treated immediately by prolonged flushing of the eye with copious amounts of clean water or saline. If irritation persists, obtain professional ophthalmologic care. /Pyrethroids/
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. 88
Gastrointestinal decontamination. If large amounts of pyrethroids, especially the cyano-pyrethroids, have been ingested and the patient is seen soon after exposure, consider gastrointestinal decontamination ... . Based on observations in laboratory animals and humans, large ingestions of allethrin, cismethrin, fluvalinate, fenvalerate, or deltamethrin would be the most likely to generate neurotoxic manifestations. If only small amounts of pyrethroid have been ingested, or if treatment has been delayed, oral administration of activated charcoal and cathartic probably represents optimal management. Do not give cathartic if patient has diarrhea or on ileus. /Pyrethroids/
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. 88-9
Other treatments. Several drugs are effective in relieving the pyrethroid neurotoxic manifestations observed in deliberately poisoned laboratory animals, but none has been tested in human poisonings. Therefore, neither efficacy nor safety under these circumstances is known. Furthermore, moderate neurotoxic symptoms and signs are likely to resolve spontaneously if they do occur. /Pyrethroids/
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. 89
For more Antidote and Emergency Treatment (Complete) data for PERMETHRIN (10 total), please visit the HSDB record page.

14.1.21 Medical Surveillance

Initial medical screening: Employees should be screened for history of certain medical conditions ... which might place the employee at increased risk from /pyrethroid/ exposure. Chronic respiratory disease: In persons with chronic respiratory disease, especially asthma, the inhalation of /pyrethroids/ might cause exacerbation of symptoms due to its sensitizing properities. Skin disease: /Pyrethroids/ can cause dermatitis which may be allergic in nature. Persons with pre-existing skin disorders may be more susceptible to the effects of this agent. Any employee developing the above-listed conditions should be referred for further medical examination. /Pyrethrum/
Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 1

14.1.22 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ To assess the human tolerance, absorption, and persistence of permethrin when used against human lice, 10 adult volunteers (four men, six women) were treated with 15-40 mL of permethrin (25:75) (1%) head louse solution. Their hair was allowed to dry naturally and then washed with baby shampoo. Urine samples were collected at 0-24, 24-48, 120-144, and 336-360 hr to measure dermal absorption. On assessment, 3 out of 10 volunteers developed mild, patchy erythema, which faded between days 4-7. Permethrin excretion during the first 24 hr was only about 1% of the applied dose, while the cumulative maximum over 14 days was only about 5.5 mg.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
/HUMAN EXPOSURE STUDIES/ In a study to assess the degree the dermal absorption of permethrin from impregnated clothing, a group of 10 male volunteer soldiers for 48 hr wore military clothing that had previously been treated with an aqueous suspension of permethrin (0.2% w/v). Subsequent analysis showed that the mean permethrin (25:75) concn of the shirts & trousers was 0.32 g/100 g. However, the average individual exposure to permethrin was 3.8 mg/day. No volunteers complained of irritation & there were no abnormal findings on physical examination.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
/HUMAN EXPOSURE STUDIES/ The difference in the degree of paraesthesia induced by a number of pyrethroids /was studied/. On five occasions, 0.05 mL of field-strength-formulated permethrin (0.13 mg/cu m) was applied to a 4 cu cm area of earlobe. The opposite earlobe received distilled water. Participant evaluation after each application continued for 48 hr and involved description of the cutaneous sensations. Each participant was treated after each application with one of the remaining compounds. Permethrin, like the other pyrethroids, induced skin sensations. Paraesthesia developed with a latency period of approximately 30 min, peaked by 8 hr, and deteriorated within 24 hr. In the case of permethrin these sensations were approximately four times less marked than those induced by cypermethrin and fenvalerate, which both contain an alpha-cyano-group. It was also found that local application of di-alpha-tocopheryl acetate markedly inhibited the occurrence of skin sensations.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
/HUMAN EXPOSURE STUDIES/ When dermally exposed to permethrin (25:75) 1% w/w in soft paraffin for up to 9 days using a patch test, 2 out of 17 volunteers developed mild erythema.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
For more Human Toxicity Excerpts (Complete) data for PERMETHRIN (29 total), please visit the HSDB record page.

14.1.23 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ In a study 0.1 mL of undiluted technical permethrin (91.35 purity) was applied to the eyes of Japanese White rabbits. The eyes were washed with distilled water 5 min or 24 hr after the application of permethrin. No eye irritation was observed.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
/LABORATORY ANIMALS: Acute Exposure/ Even though permethrin is about 30 times more toxic to houseflies than pyrethrinI, it is substantially less toxic to rats. The oral and intravenous LD50 values in rats are 1,500 and >270 mg/kg, respectively. Other studies indicate oral LD50 values of 3800 and 410 mg/kg in female rats for the undiluted compound and for the active ingredient dissolved in an unsaturated oil, respectively. Dermal application for 21 days elicited no toxicity.
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 81
/LABORATORY ANIMALS: Acute Exposure/ Permethrin has a low acute toxicity to rats, mice, rabbits, and guinea-pigs, though the LD50 value varies considerably according to the vehicle used and the cis-trans isomeric ratio. Signs of acute poisoning become apparent within 2 hr of dosing and persist for up to 3 days. (1R,cis)- and (1R,trans)-permethrin belong to the type I group of pyrthroids, which typically cause tremor (T-syndrome), incoordination, hyperactivity, prostration, and paralysis. Core temperature is markedly incr during poisoning.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 11, 2014: https://www.inchem.org/pages/ehc.html
/LABORATORY ANIMALS: Acute Exposure/ Permethrin caused a mild primary irritation of the intact and abraded skin of rabbits but did not cause a photochemical irritation reaction after exposure of treated areas of rabbit skin to uv light. Permethrin did not cause a sensitization reaction in guinea-pigs.
WHO; Environmental Health Criteria 94: Permethrin (1990). Available from, as of August 6, 2014: https://www.inchem.org/pages/ehc.html
For more Non-Human Toxicity Excerpts (Complete) data for PERMETHRIN (82 total), please visit the HSDB record page.

14.1.24 Non-Human Toxicity Values

LD50 Rat oral 1,500 mg/kg
Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 81
LD50 Rat oral 600 mg/kg
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V13 458 (1981)
LD50 Rat oral 1,300 mg/kg
Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-261
LD50 Rat oral 430-4000 mg/kg /cis:trans-isomer ratio of 40:60/
Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 785
For more Non-Human Toxicity Values (Complete) data for PERMETHRIN (30 total), please visit the HSDB record page.

14.1.25 Ongoing Test Status

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; See the data in Chemical Explorer/[USEPA; ICSS Dashboard Application; Available from, as of March 28, 2014: http://actor.epa.gov/dashboard/]

14.2 Ecological Information

14.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

14.2.2 Ecotoxicity Values

LD50; Species: Anas platyrhynchos (Mallard Duck) age 19 months; oral via capsule >2000 mg/kg
USEPA/Office of Pesticide Programs; Pesticide Ecotoxicity Database (2013) as cited in the ECOTOX database. Available from, as of August 14, 2014
LC50; Species: Anas platyrhynchos (Mallard Duck) age 7 days; diet (chemical incorporated into food) >5200 ppm for 8 days
USEPA/Office of Pesticide Programs; Pesticide Ecotoxicity Database (2013) as cited in the ECOTOX database. Available from, as of August 14, 2014
LD50; Species: Anas platyrhynchos (Mallard Duck) adult; oral via capsule >9868 mg/kg
USEPA/Office of Pesticide Programs; Pesticide Ecotoxicity Database (2013) as cited in the ECOTOX database. Available from, as of August 14, 2014
LD50; Species: Anas platyrhynchos (Mallard Duck) age 14 days; oral via capsule >4640 mg/kg
USEPA/Office of Pesticide Programs; Pesticide Ecotoxicity Database (2013) as cited in the ECOTOX database. Available from, as of August 14, 2014
For more Ecotoxicity Values (Complete) data for PERMETHRIN (55 total), please visit the HSDB record page.

14.2.3 Ecotoxicity Excerpts

/BIRDS and MAMMALS/ The highest acute Risk Quotient is approximately 0.03 for birds feeding on short grass and 0.04 for the smallest mammals feeding on short grass.
USEPA; Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision (RED) for Permethrin (52645-53-1). EPA738-R-09-306 p. 78 (May 2009). Available from, as of January 31, 2014: https://www.epa.gov/pesticides/reregistration/status_page_b.htm
/AQUATIC SPECIES/ Pyrethroids, the widely used pesticides, are highly toxic to aquatic organisms. However, little information is so far available regarding the joint toxicity of type I and type II pyrethroids to fish. Zebrafish is a well-accepted aquatic vertebrate model for toxicity assessment due to small size, easy husbandry, high fecundity and transparent embryos. In this study, embryo-larval zebrafish /was utilized/ to elucidate the combined effects of sublethal concentrations of permethrin (PM) and cypermethrin (CP), which are the most frequently used type I and type II pyrethroids, respectively. Fish were exposed from 3hr postfertilization (hpf) to 144 hpf to binary mixtures of nominal concentrations of 100, 200, 300ug/L PM (PM100, PM200, PM300) and 10, 20, 30ug/L CP (CP10, CP20, CP30). Analytical data of the real concentrations of the chemicals showed a significant degradation of the pyrethroids but an obvious recovery after the renewal of the exposure solution. Defect rates of embryos exposed to these low concentrations of single PM or CP exhibited no statistically significant difference from the control, while the application of combination of PM and CP resulted in deleterious effects on zebrafish embryonic development. In all PM200 and PM300 exposure groups, increasing CP concentrations acted additively to the action of PM in terms of all sublethal endpoints. Co-treatment of embryos with the specific sodium channel blocker MS-222 and pyrethroids (individuals or the mixture) caused a decline in the incidences of body axis curvature and spasms compared to treatment of animals with pyrethroids alone, suggesting that the developmental toxicity of PM and CP to zebrafish was related to disruption of ion channels. We further revealed that mixture of the two pyrethroids caused greater down-regulation in the mRNA levels of proneural genes. The individual pesticides had no effect on the activity of superoxide dismutase (SOD), while the mixture exposure caused significant induction. Treatment with CP or the mixture increased the activity of catalase (CAT). Taken together, our data indicated that the mixture of PM and CP caused higher incidence of morphological defects, greater inhibition in proneural gene expression and more oxidative stress, compared to the single chemical at the corresponding doses. Our findings suggest that the combination of type I and type II pyrethroids poses a greater risk to fish in the water column. /Pyrethroids/
Yang Y et al; Chemosphere 96: 146-54 (2014)
/AQUATIC SPECIES/ While the lethal toxicity of pyrethroid insecticides to fish is well documented, their sublethal physio-behavioral effects remain poorly characterized. Known pyrethroid-associated changes to insect neuromuscular function may translate into similar effects in fish, thereby altering swimming ability and affecting foraging, predator avoidance, and migration. Three experiments were conducted using critical (Ucrit) and burst (Umax) swimming speeds to assess the sublethal effects of the pyrethroids permethrin and deltamethrin in juvenile rainbow trout (Oncorhynchus mykiss). Fish were exposed to deltamethrin (100, 200, or 300 ng/L) or permethrin (1, 2, or 3 ug/L) in water for 4 d, and assessed for swimming performance. Deltamethrin (200 and 300 ng/L) reduced Ucrit, but not Umax, while both swim performance measurements were unaffected by permethrin. Subsequent experiments used only Ucrit to assess deltamethrin exposure. In a time course experiment, deltamethrin (300 ng/L) reduced Ucrit after 1 and 4 d of exposure, but after 7 d of exposure Ucrit was fully recovered. Finally, deltamethrin (1, 2, or 3 ug/L) reduced Ucrit after 1h bath exposures similar to recommended protocols for deltamethrin based sea-lice treatment in aquaculture. The real-world implications of the revealed pyrethroid-associated swimming ability reductions in salmon may be important in areas close to aquaculture facilities.
Goulding AT et al; Comp Biochem Physiol C Toxicol Pharmacol 157 (3): 280-6 (2013)
/AQUATIC SPECIES/ Pyrethroid insecticides are widely used on agricultural crops, as well as for nurseries, golf courses, urban structural and landscaping sites, residential home and garden pest control, and mosquito abatement. Evaluation of sensitive marine and estuarine species is essential for the development of toxicity testing and risk-assessment protocols. Two estuarine crustacean species, Americamysis bahia (mysids) and Palaemonetes pugio (grass shrimp), were tested with the commonly used pyrethroid compounds, lambda-cyhalothrin, permethrin, cypermethrin, deltamethrin, and phenothrin. Sensitivities of adult and larval grass shrimp and 7-day-old mysids were compared using standard 96-h LC(50) bioassay protocols. Adult and larval grass shrimp were more sensitive than the mysids to all the pyrethroids tested. Larval grass shrimp were approximately 18-fold more sensitive to lambda-cyhalothrin than the mysids. Larval grass shrimp were similar in sensitivity to adult grass shrimp for cypermethrin, deltamethrin, and phenothrin, but larvae were approximately twice as sensitive to lambda-cyhalothrin and permethrin as adult shrimp. Acute toxicity to estuarine crustaceans occurred at low nanogram per liter concentrations of some pyrethroids, illustrating the need for careful regulation of the use of pyrethroid compounds in the coastal zone. /Pyrethroid/
E Delorenzo M et al; Environ Toxicol (2013)
For more Ecotoxicity Excerpts (Complete) data for PERMETHRIN (11 total), please visit the HSDB record page.

14.2.4 US EPA Regional Screening Levels for Chemical Contaminants

Resident Soil (mg/kg)
3.20e+03
Industrial Soil (mg/kg)
4.10e+04
Tapwater (ug/L)
1.00e+03
MCL (ug/L)
1.5E+01(G)
Risk-based SSL (mg/kg)
2.40e+02
Chronic Oral Reference Dose (mg/kg-day)
5.00e-02
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

14.2.5 US EPA Regional Removal Management Levels for Chemical Contaminants

Resident Soil (mg/kg)
9.50e+03
Industrial Soil (mg/kg)
1.20e+05
Tapwater (ug/L)
3.00e+03
MCL (ug/L)
1.5E+01 (G)
Chronic Oral Reference Dose (mg/kg-day)
5.00e-02
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

14.2.6 ICSC Environmental Data

The substance is very toxic to aquatic organisms. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.

14.2.7 Environmental Fate / Exposure Summary

Permethrin's production may result in its release to the environment through various waste streams; its use as a broad spectrum insecticide will result in its direct release to the environment. If released to air, a vapor pressure of 5.18X10-8 mm Hg at 25 °C indicates permethrin will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase permethrin will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone; the half-lives for these reactions in air are estimated to be 17 hours and 49 days, respectively. Particulate-phase permethrin will be removed from the atmosphere by wet and dry deposition. Permethrin is susceptible to direct photolysis in sunlight. If released to soil, permethrin is expected to have no mobility based upon a Koc range from 10,471 to 86,000. Volatilization from moist soil surfaces is possible based upon an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole. However, adsorption to soil is expected to attenuate soil volatilization. Permethrin degrades in soil through biodegradation and abiotic hydrolysis. Direct photolysis can occur on soil surfaces exposed to sunlight. Trans-permethrin has been shown to degrade faster in soil and sediment than the cis-isomer. Field dissipation half-lives for permethrin generally fall in the range from 6 to 106 days. Under aerobic conditions, the field dissipation half-life is roughly 30 days (4-40 day range) and under anaerobic conditions, the field dissipation half-life is roughly 108 days (3-204 day range). If released into water, permethrin is expected to adsorb to suspended solids and sediment based upon its Koc values. Volatilization from water surfaces is possible based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 39 days and 289 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. BCF values for rainbow trout and sheepshead minnow of approx 560 and 480, respectively, suggest bioconcentration in aquatic organisms is high. At pH 4, pH 5 and pH 7 (25 °C), permethrin is stable towards abiotic hydrolysis; at pH 9, the abiotic hydrolysis half-life is in the range of 37-50 days. The direct photolysis half-life in water is about 23 to 37 days. Reaction with photo-oxidant species in natural waters can decrease the photodegradation half-life. The biodegradation half-life of permethrin in a sediment-seawater solution was less than 2.5 days. Occupational exposure to permethrin may occur through inhalation and dermal contact with this compound at workplaces where permethrin is produced or used. Monitoring/use data indicate that the general population may be exposed to permethrin via inhalation of ambient air and ingestion of food and drinking water, and dermal contact through the household use of consumer products containing permethrin. (SRC)

14.2.8 Artificial Pollution Sources

Permethrin's production and registered for use in/on modes of transportation, structures, buildings, pets, and clothing (impregnated and ready to use formulations) may result in its release to the environment through various waste streams(SRC). Additionally, permethrin has non-FIFRA pharmaceutical uses as a pediculicide for the treatment of head lice and scabies(1). Its use in/on numerous food/feed crops, livestock and livestock housing, Public Health Mosquito abatement programs, and numerous indoor and outdoor residential spaces(1) will result in its direct release to the environment(SRC).
(1) USEPA/OPPTS; Reregistration Eligibility Decisions (REDs) for Permethrin (Revised May 2009). EPA 738-R-09-306. Available from, as of Mar 3, 2014: https://www.epa.gov/pesticides/reregistration/status.htm

14.2.9 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 10,471 to 86,000(2), indicate that permethrin is expected to be immobile in soil(SRC). Volatilization of permethrin from moist soil surfaces is possible(SRC) given an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 5.18X10-8 mm Hg(3), and water solubility, 0.0111 mg/L(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Permethrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Permethrin is susceptible to biodegradation in soil and sediment as demonstrated by incubation studies using sterile and non-sterile conditions(4,5). Degradation in soil and sediments occurs through biodegradation and abiotic hydrolysis(6). Permethrin is susceptible to direct photolysis on soil surfaces exposed to sunlight(3); cis- and trans-permethrin photolysis half-lives of 23.1 and 36.8 days have been measured in water respectively(3). The degradation half-life of permethrin in aerobically incubated soil was less than 4 weeks, and the degradation of the trans-isomer was more rapid than the cis-isomer(7). Faster degradation of the trans-isomers versus the cis-isomers was also observed in soil and sediment studies(8). In two Japanese soils, both the 1R, trans- and 1R, cis-isomers were rapidly degraded under dry conditions with half-lives of less than 2 days(9). Under anaerobic conditions in flooded silt loam soils, degradation half-lives were 32-34 days for 14C-labeled trans-permethrin and greater than 64 days for 14C-labeled cis-permethrin(7). Field dissipation half-lives for permethrin generally fall in the range from 6 to 106 days with 42 days as a selected value for modeling(2). Under aerobic conditions, the field dissipation half-life is roughly 30 days (4-40 day range) and under anaerobic conditions, the field dissipation half-life is roughly 108 days (3-204 day range)(2).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) USDA; Agric Res Service. ARS Pesticide Properties Database. Last Updated Nov 6, 2009. Permethrin (52645-53-1). Available from, as of Mar 4, 2014: https://www.epa.gov/reg3hwmd/risk/human/rb-concentration_table/userguide/ARSPesticideDatabaseUSDA2009.pdf
(3) World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009); Available, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
(4) Schimmel SC et al; J Agric Food Chem 31: 104-13 (1983)
(5) Qin S et al; J Agric Food Chem 54: 5040-5045 (2006)
(6) USEPA/OPPTS; Reregistration Eligibility Decisions (REDs) for Permethrin (Revised May 2009). EPA 738-R-09-306. Available from, as of Mar 3, 2014: https://www.epa.gov/pesticides/reregistration/status.htm
(7) Jordan EG and Kaufman DD; J Agric Food Chem 34: 880-4 (1986)
(8) Qin S, Gan J; J Agric Food Chem 54: 9145-9151 (2006)
(9) Crosby DG; pp. 194-213 in Pyrethrum Flowers. Casida JE, Quidstad GB, eds. New York, NY: Oxford Univ Press (1995)
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 10,471 to 86,000(2), indicate that permethrin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is possible(3) based upon an estimated Henry's Law constant of 2.2X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 5.18X10-8 mm Hg(4), and water solubility, 0.00111 mg/L(4). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 39 days and 289 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond exceeds 100 years if adsorption is considered(6). According to a classification scheme(7), BCF values of approximately 560 and 480 for rainbow trout (Oncorhynchus mykiss) and sheepshead minnow (Cyprinodon vagiegatus), respectively(8,9), suggests the potential for bioconcentration in aquatic organisms is high(SRC). At pH 4, pH 5 and pH 7 (25 °C), permethrin is stable towards abiotic hydrolysis(2,4). At pH 9, the abiotic hydrolysis rate constant is 0.0139 per day at 25 °C(2) which corresponds to a half-life of 50 days(SRC). The hydrolysis half-lives of cis- and trans-permethrin at pH 9(25 °C, sterile water) have been measured as 42.3 and 37.7 days respectively(4). In water, a photolysis rate constant of 0.021 per day has been reported(2) which corresponds to photodegradation half-life of 33 days(SRC). In sterile buffer solutions (pH 4) exposed to irradiation equivalent to natural sunlight (Tokyo, 35 deg N, April-June), cis- and trans-permethrin had photolysis half-lives of 23.1 and 38.6 days respectively(4); using synthetic humic water, the photolysis half-lives decreased to 14.6 and 25.5 days respectively(2). The photolysis half-life of permethrin in seawater exposed to outdoor light was determined to be 14 days(9). Photolysis half-lives of 27.1 and 19.6 hrs were determined for respective cis- and trans-isomers in 800 mL pond water exposed to sunlight(10). Faster photodegradation in humic and natural waters can result from reaction with photo-oxidant species such hydroxyl radicals, peroxy radicals and singlet oxygen(11). Permethrin is susceptible to biodegradation as demonstrated by incubation studies using sterile and non-sterile conditions(9,12). The biodegradation half-life of permethrin in a sediment-seawater solution was less than 2.5 days(9); under sterile conditions there was no significant change in permethrin concentration(9).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) USDA; Agric Res Service. ARS Pesticide Properties Database. Last Updated Nov 6, 2009. Permethrin (52645-53-1). Available from, as of Mar 4, 2014: https://www.epa.gov/reg3hwmd/risk/human/rb-concentration_table/userguide/ARSPesticideDatabaseUSDA2009.pdf
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(4) World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009). Available from, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
(5) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 4, 2014: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(6) USEPA; EXAMS II Computer Simulation (1987)
(7) Franke C et al; Chemosphere 29: 1501-14 (1994)
(8) Haitzer M et al; Chemosphere 37: 1335-62 (1998)
(9) Schimmel SC et al; J Agric Food Chem 31: 104-13 (1983)
(10) Rawn GP et al; J Environ Sci Health B17: 463-86 (1982)
(11) Mill T; p. 368 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(12) Qin S et al; J Agric Food Chem 54: 5040-5045 (2006)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), permethrin, which has a vapor pressure of 5.18X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase permethrin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-life for reaction with hydroxyl radicals in air is estimated to be 17 hours(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule-sec at 25 °C(3); the half-life for reaction with ozone in air is estimated to be 49 days(SRC), calculated from its rate constant of 2.3X10-19 cu cm/molecule-sec at 25 °C(3). Particulate-phase permethrin may be removed from the air by wet and dry deposition(SRC). Permethrin absorbs light in the environmental spectrum(4) and has been shown to photodegrade in sunlight(2); therefore, permethrin can degrade through direct photolysis(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009); Available, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
(3) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 4, 2014: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(4) Chen ZM et al; Ind Eng Chem Prod Res Dev 23: 5-11 (1984)

14.2.10 Environmental Biodegradation

AEROBIC: The half-life of permethrin in aerobically incubated soil is less than 4 weeks, and the degradation of the trans isomer is more rapid than the cis isomer(1). Permethrin was stable in sterile Hagerstown silty clay loam indicating that any degradation probably was microbial(2); as expected ester hydrolysis predominated in non-sterile soil(2). In two Japanese soils, both the 1R, trans- and 1R, cis-isomers were rapidly degraded under dry conditions with half-lives of less than 2 days(2). The half-life in a sediment-seawater solution was less than 2.5 days; under sterile conditions there was no significant change in permethrin concentration(3). Aerobic incubation of 14C-labeled cis- and trans-isomers and stereo-isomers of permethrin in turfgrass soil and coverground soil from California resulted in losses of 68.6-78.9% and 86.3-90.4% after 14 days for the cis- and trans-isomers respectively, and 93.0-99.2% and 95.4-98.5% after 56 days for the cis- and trans-isomers respectively(4); degradation products included cyclopropanoic acid, 3-phenoxybenzoic acid and 3-phenoxybenzyl alcohol(4); degradation losses in sediment were greater under aerobic conditions compared to anaerobic conditions after 14 days (trans-isomers had 76.2-81.2% loss under aerobic conditions and 65.7-74.1% loss under anaerobic conditions)(4). Stereo-isomers of cis-permethrin had half-lives of 139-141 days when incubated in sterilized soil or sediments and half-lives of 99-126 days in non-sterile aerobic or anaerobic soil or sediments(5).
(1) Jordan EG, Kaufman DD; J Agric Food Chem 34: 880-4 (1986)
(2) Crosby DG; pp. 194-213 in Pyrethrum Flowers. Casida JE, Quidstad GB, eds. New York, NY: Oxford Univ Press (1995)
(3) Schimmel SC et al; J Agric Food Chem 31: 104-13 (1983)
(4) Qin S, Gan J; J Agric Food Chem 54: 9145-9151 (2006)
(5) Qin S et al; J Agric Food Chem 54: 5040-5045 (2006)
ANAEROBIC: Under anaerobic conditions in flooded silt loam soils, degradation half-lives were 32-34 days for 14C-labeled trans-permethrin and greater than 64 days for 14C-labeled cis-permethrin(1). Anaerobic incubation of 14C-labeled cis- and trans-isomers and stereo-isomers of permethrin in San Diego Creek sediment from California resulted in losses of 46.7-54.8% and 65.7-74.1% after 14 days for the cis- and trans-isomers respectively, and 69.7-75.2% and 75.6-86.6% after 56 days for the cis- and trans-isomers respectively(2).
(1) Jordan EG, Kaufman DD; J Agric Food Chem 34: 880-4 (1986)
(2) Qin S, Gan J; J Agric Food Chem 54: 9145-9151 (2006)
PURE CULTURE: Pure cultures of Bacillus cereus, Pseudomonas fluorescens, and Achromobacter sp. transformed permethrin to 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid, 3-phenoxybenzyl alcohol, 3-phenoxy benzoic acid, and 4-hydroxy-3-phenoxybenzoic acid; half-life of less than 5 days(1).
(1) Maloney SE et al; Appl Environ Microb 54: 2874-6 (1988)

14.2.11 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of permethrin with photochemically-produced hydroxyl radicals has been estimated as 2.30X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of permethrin with photochemically-produced ozone has been estimated as 2.33X10-19 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 49 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). In sterile buffer solutions at pH 4, 7 and 9 (25 °C), both cis- and trans-isomers of permethrin were found to be stable at pH 4 and pH 7(2); at pH 9, cis-permethrin had a hydrolysis half-life of 42.3 days and trans-permethrin had a half-life of 37.7 days(2). At pH 5 and pH 7, permethrin was stable towards abiotic hydrolysis(3); at pH 9, the abiotic hydrolysis rate constant is 0.0139 per day at 25 °C(3) which corresponds to a half-life of 50 days(SRC). In water and soil, the photolysis rate constants are reported to be 0.021 and 0.023 per day, respectively(3); these correspond to photodegradation half-lives of 33 and 30 days, respectively(SRC). In sterile buffer solutions (pH 4) exposed to irradiation equivalent to natural sunlight (Tokyo, 35 deg N, April-June) for 30 days, cis- and trans-permethrin had photolysis half-lives of 23.1 and 38.6 days respectively(2); using synthetic humic water, the photolysis half-lives decreased to 14.6 and 25.5 days respectively(2). The photodegradation rate of permethrin on thin films in the 295-305 nm wavelength region was determined to range from 15.9X10-7 to 4.7X10-7 1/sec-1 which corresponds to a half-life of 5-17 days, respectively(4). Photolysis half-lives of 27.1 and 19.6 hrs were determined for respective cis- and trans-isomers in 800 mL pond water exposed to sunlight(5). The photolysis half-life of permethrin in seawater exposed to outdoor light was determined to be 14 days(6).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 4, 2014: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009); Available, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
(3) USDA; Agric Res Service. ARS Pesticide Properties Database. Last Updated Nov 6, 2009. Permethrin (52645-53-1). Available from, as of Mar 4, 2014: https://www.epa.gov/reg3hwmd/risk/human/rb-concentration_table/userguide/ARSPesticideDatabaseUSDA2009.pdf
(4) Chen ZM et al; Ind Eng Chem Prod Res Dev 23: 5-11 (1984)
(5) Rawn GP et al; J Environ Sci Health B17: 463-86 (1982)
(6) Schimmel SC et al; J Agric Food Chem 31: 104-13 (1983)

14.2.12 Environmental Bioconcentration

The BCF values for permethrin in rainbow trout (Oncorhynchus mykiss) and sheepshead minnow (Cyprinodon vagiegatus) were approximately 560 and 480, respectively(1,2). According to a classification scheme(3), these BCF values suggest the potential for bioconcentration in aquatic organisms is high(SRC). A BCF of 1,900 was also reported for oysters(2). Insect BCF values after 6 hr of exposure to sublethal permethrin concentrations were 18, 30, 7, 4, and 24 for black fly, caddisfly, damsefly, water scavenger, and mayfly, respectively(4).
(1) Haitzer M et al; Chemosphere 37: 1335-62 (1998)
(2) Schimmel SC et al; J Agric Food Chem 31: 104-13 (1983)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)
(4) Tang JX, Siegfried BD; Bull Environ Contam Toxicol 57: 993-998 (1996)

14.2.13 Soil Adsorption / Mobility

Koc values for permethrin range from 10,471 to 86,000 that were measured in a variety of different soils including silt loam, sandy loam, sediments and sand(1); the selected Koc value (for use in modeling) is 39,300(1). Koc values for silt loam (Ohio), sandy loam (Wisconsin), sediment (Georgia), and sand (Florida) were 19,300 (Kd = 236; organic matter, 0.71%), 20,900 (Kd = 217; organic matter, 0.60%), 44,700 (Kd = 401; organic matter, 0.91%), and 60,900 (Kd = 140; organic matter, 0.13%), respectively(1). The Kd for permethrin was measured to be 400 on a red earth soil from Australia with an organic matter content of 1.09%(2) which corresponds to a Koc of about 63,100(SRC). According to a classification scheme(3), these Koc values suggest that permethrin is expected to be immobile in soil(SRC). The distribution coefficients (Kd) for permethrin on clean (i.e., without organic matter) montomorillonite, aluminum oxide and kaolinite clay mineral surfaces were 61, 41, and 5 ml/g, respectively(4).
(1) USDA; Agric Res Service. ARS Pesticide Properties Database. Last Updated Nov 6, 2009. Permethrin (52645-53-1). Available from, as of Mar 4, 2014: https://www.epa.gov/reg3hwmd/risk/human/rb-concentration_table/userguide/ARSPesticideDatabaseUSDA2009.pdf
(2) Briggs GG; J Agric Food Chem 29: 1050-9 (1981)
(3) Swann RL et al; Res Rev 85: 17-28 (1983)
(4) Zhou JL et al; Wat Res 29: 1023-31 (1995)

14.2.14 Volatilization from Water / Soil

The Henry's Law constant for permethrin is estimated as 2.4X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 5.18X10-8 mm Hg(1), and water solubility, 0.0111 mg/L(1). This Henry's Law constant indicates that permethrin is expected to volatilize from water surfaces(2). 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 39 days(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 289 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond exceeds 100 years if adsorption is considered(3). Permethrin's Henry's Law constant and adsorption to soil indicates that volatilization from moist soil surfaces is not expected to be an important fate process(SRC). Permethrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure.
(1) World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009); Available, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) USEPA; Exams II Computer Simulation (1987)

14.2.15 Environmental Water Concentrations

GROUNDWATER: As part of the National Drinking Water Contaminant Occurrence Database (NDOD), permethrin was detected in 3 of 5,728 ambient groundwater samples at an average concentration of 0.011 ug/L (max, 0.02; min, 0.006)(1). [
(1) USEPA; National Drinking Water Contaminant Occurrence Database (NDOD) for Permethrin (52645-53-1). May 4, 2000. Available from, as of Mar 5, 2014: https://water.epa.gov/scitech/datait/databases/drink/ncod/databases-index.cfm
SURFACE WATER: As part of the National Drinking Water Contaminant Occurrence Database (NDOD), permethrin was detected in 3 of 73 ambient spring water samples at an average concentration for positive samples of 0.0133 ug/L (max, 0.02; min, 0.01)(1); permethrin was also detected in 24 of 12,253 other ambient surface water samples at an average concentration for positive samples of 0.0137 ug/L (max, 0.03; min, 0.005)(1). Permethrin was detected 6 hrs post-application at concentrations of 17 and 18 ng/L in 2 of 6 samples from a creek approximately 60-100 m from a potato field where permethrin was applied via aerial spraying(2). In 1996, permethrin concentration in surface waters from agricultural areas in Thailand was 2.81 ug/L(3). The percentage of freshwater samples in England and Wales (UK) with concentrations of permethrin exceeding 0.01 ug/L in 1992 and 1993 were 6% of 816 samples(4). Following rainfall events in Feb 2009, permethrin was detected in the Alamo Creek CA at a concentration of 10.9 ng/L and in the San Joaquin River CA at 6.8 ng/L(5).
(1) USEPA; National Drinking Water Contaminant Occurrence Database (NDOD) for Permethrin (52645-53-1). Available from, as of Mar 5, 2014: https://water.epa.gov/scitech/datait/databases/drink/ncod/databases-index.cfm
(2) Frank R et al; Environ Monit Assess 16: 137-50 (1991)
(3) Thapinta A, Hudak PF; Environ Monit Assess 60: 103-114 (2000)
(4) Eke KR; Pestic Outlook 7: 15-20 (1996)
(5) Weston DP, Lydy MJ; Environ Sci Technol 44: 1833-1840 (2010)

14.2.16 Sediment / Soil Concentrations

SEDIMENT: Suspended sediment samples collected from five locations in California in the fall of 2009 contained permethrin concentrations of 1.8-9.6 ng/L(1); permethrin was not detected in the water-phase (detection limit of 0.6 ng/l)(1).
(1) Hladik ML, Kuivila KM; J Agric Food Chem 57: 9079-9085 (2009)
SOIL: Permethrin was detected in the hydrosoil of a model outdoor pond at a concentration of 1 ug/kg one year after treatment with 15 ug/L permethrin(1). Permethrin was detected 30 days post-application at a concentration of 10 ug/kg in 1 of 3 sediment samples from a creek approximately 60-100 m from a potato field where permethrin was applied via aerial spraying(2). Between 1996-1997, the concentration of permethrin in soil samples from cultivated areas in Thailand ranged from 62.41 to 1,178.40 ug/kg (24 samples)(3). The average concentration of permethrin in the soil collected from 49 agrichemical facilities located throughout Illinois was 190 ug/kg (range, 11 to 4.22X10+5 ug/kg)(4). Yard soil samples collected from 11 homes in Atlanta GA during Jan-April 2006 contained positive cis- and trans-permethrin concentrations of 2.42-7.78 ng/g dry wt(5).
(1) Rawn GP et al; J Environ Sci Health B17: 463-86 (1982)
(2) Frank R et al; Environ Monit Assess 16: 137-50 (1991)
(3) Thapinta A, Hudak PF; Environ Monit Assess 60: 103-114 (2000)
(4) Krapac IG et al; J Soil Contam 43: 209-226 (1995)
(5) Riederer AM et al; Arch Environ Contam Toxicol 58: 908-917 (2010)

14.2.17 Atmospheric Concentrations

URBAN: The mean concentration of permethrin residues in air particulates after use of the pesticide in the Muna Valley region of Saudi Arabia ranged from 6.35 to 15.67 ug/cu m(1).
(1) Badawy MI; Bull Environ Contam Toxicol 60: 693-701 (1998)
INDOOR AIR: According to a pilot investigation of pesticides in 9 homes in Jacksonville, FL during August of 1985, permethrin was qualitatively detected in the outdoor air (porch or patio) of 2 homes(1). The concentration of cis- and trans-permethrin in household dust ranged between 255-2850 and 365-3850 ug/kg, respectively, for 4 of 7 NJ homes in 1985(2). In 1993, permethrin was detected in the ambient air of insecticide storage and office rooms of a commercial pest control building in North Carolina at a mean concentration of 0.45 ug/cu m(3).
(1) Lewis RG et al; Environ Monit Assess 10: 59-73 (1988)
(2) Roinstad KS et al; J AOAC Int 76: 1121-26 (1993)
(3) Wright CG et al; Bull Environ Contam Toxicol 56: 21-28 (1996)

14.2.18 Food Survey Values

During October 1, 1981 and September 30, 1986, permethrin was found in 309 U.S. agricultural commodity samples at a concentration range of >0-0.05 ppm, 155 samples at 0.05-0.1 ppm, 283 samples at 0.1-0.5 ppm, 104 samples at 0.5-1.0 ppm, 51 samples at 1.0-2.0 ppm, and 17 agricultural commodity samples at a concentration >2.0 ppm(1). This study does not distinguish between domestic and imported commodities or between surveillance and compliance samples(1). During October 1, 1981 and September 30, 1986, permethrin was found in 89 U.S. domestic agricultural commodities conducted by surveillance sampling at a concentration range of >0-0.05 ppm, 75 samples at 0.05-0.1 ppm, 217 samples at 0.1-0.5 ppm, 100 samples at 0.5-1.0 ppm, 47 samples at 1.0-2.0 ppm, and 11 domestic agricultural commodities at a concentration >2.0 ppm(2). During October 1, 1981 and September 30, 1986, permethrin was found in 234 U.S. imported agricultural commodities conducted by surveillance sampling at a concentration range of >0-0.05 ppm, 97 samples at 0.05-0.1 ppm, 36 samples at 0.1-0.5 ppm,1 sample at 0.5-1.0 ppm, and 1 imported agricultural commodity sample at a concentration 1.0-2.0 ppm(2). As part of the FDA Total Diet Study in 1992-1993, the max concentration of permethrin (total) in domestic and imported tomatoes was 0.28 ppm (24% of samples) and 0.38 ppm (26% of samples), respectively(3); the average concentration (weighted) in imported tomatoes was 0.03 ppm(3).
(1) Luke MA et al; J Assoc Off Anal Chem 71: 415-20 (1988)
(2) Hundley HK et al; J Assoc Off Anal Chem 71: 875-92 (1988)
(3) Roy RR et al; J AOAC Int 78: 930-40 (1995)
cis-Permethrin Concentrations - FDA Total Diet Study Market Baskets (1991-93) (1).
Commodity
ham, baked
Concn (ppm)
0.001
Commodity
peaches, strained/junior
Concn (ppm)
0.0185
Commodity
eggs, fried
Concn (ppm)
0.001
Commodity
pears, strained/junior
Concn (ppm)
0.0013
Commodity
peanuts, dry roasted
Concn (ppm)
0.006
Commodity
fruit dessert/pudding, strained/junior
Concn (ppm)
0.0045
Commodity
popcorn, popped in oil
Concn (ppm)
0.007
Commodity
veal cutlet, pan-cooked
Concn (ppm)
0.002
Commodity
rye bread
Concn (ppm)
0.0099
Commodity
cracked wheat bread
Concn (ppm)
0.0009
Commodity
peach, raw
Concn (ppm)
0.0107
Commodity
peach, canned
Concn (ppm)
0.0004
Commodity
cantaloupe, raw
Concn (ppm)
0.0045
Commodity
tomato, stewed/canned
Concn (ppm)
0.0015
Commodity
sweet cherries, raw
Concn (ppm)
0.022
Commodity
Brussels sprouts, boiled
Concn (ppm)
0.0154
Commodity
prunes, dried
Concn (ppm)
0.002
Commodity
mushrooms, raw
Concn (ppm)
0.0285
Commodity
spinach, boiled
Concn (ppm)
0.6283
Commodity
turnip, boiled
Concn (ppm)
0.001
Commodity
collards, boiled
Concn (ppm)
0.3331
Commodity
okra, boiled
Concn (ppm)
0.002
Commodity
iceberg lettuce, raw
Concn (ppm)
0.0104
Commodity
beef stroganoff
Concn (ppm)
0.018
Commodity
sauerkraut, canned
Concn (ppm)
0.0005
Commodity
green peppers, stuffed
Concn (ppm)
0.0138
Commodity
broccoli, boiled
Concn (ppm)
0.0047
Commodity
tuna noddle casserole
Concn (ppm)
0.0014
Commodity
celery, raw
Concn (ppm)
0.0113
Commodity
cheeseburger, fast-food
Concn (ppm)
0.005
Commodity
asparagus, boiled
Concn (ppm)
0.0862
Commodity
taco or tostada, carry-out
Concn (ppm)
0.0015
Commodity
cauliflower, boiled
Concn (ppm)
0.004
Commodity
cheese pizza, carry-out
Concn (ppm)
0.0006
Commodity
red tomato, raw
Concn (ppm)
0.0072
Commodity
pepperoni pizza, carry-out
Concn (ppm)
0.0006
Commodity
green beans, boiled
Concn (ppm)
0.005
Commodity
beef chow mein, carry-out
Concn (ppm)
0.0016
Commodity
green pepper, raw
Concn (ppm)
0.0332
Commodity
split peas with vegetables and ham
Concn (ppm)
0.0008
Commodity
radish, raw
Concn (ppm)
0.001
Commodity
squash, strained/junior
Concn (ppm)
0.0009
Commodity
meatloaf, homemade
Concn (ppm)
0.0006
Commodity
creamed spinach (strained/junior
Concn (ppm)
0.0372
Commodity
butter, salted
Concn (ppm)
0.002
Commodity
green beans, strained/junior
Concn (ppm)
0.0035
Commodity
half/half cream
Concn (ppm)
0.0003
Commodity
vegetables and chicken, strained/junior
Concn (ppm)
0.001
Commodity
tomato catsup
Concn (ppm)
0.0009
Commodity
chicken, strained/junior
Concn (ppm)
0.001
Commodity
pumpkin pie
Concn (ppm)
0.0024
(1) FDA; FDA Total Diet Study. Sept 2000. Available from, as Mar 6, 2014: https://www.fda.gov/Food/FoodScienceResearch/TotalDietStudy/ucm184293.htm
Permethrin food detections(1-4).
Commondity
apples, fresh
Concn
0.1 to >2 ppm
Notes
32 month period ending Dec 1991, domestic Canadian agricultural commodities conducted by surveillance sampling
Ref No.
1
Commondity
celery, fresh
Concn
<0.5 to 0.5 ppm
Notes
32 month period ending Dec 1991, imported Canadian agricultural commodities
Ref No.
1
Commondity
lettuce, fresh
Concn
<0.05-0.5 ppm
Ref No.
1
Commondity
pepper, fresh
Concn
<0.05 ppm
Ref No.
1
Commondity
spinach, fresh
Concn
<0.05-2.0 ppm
Ref No.
1
Commondity
apples, fresh
Concn
0.5-2> ppm
Notes
January 1, 1992 and March 31, 1994, domestic Canadian agricultural commodities conducted by surveillance sampling
Ref No.
2
Commondity
celery, fresh
Concn
0.5-1.0 ppm
Ref No.
2
Commondity
head lettuce, fresh
Concn
0.50 to >2.0 ppm
Ref No.
2
Commondity
spinach, fresh
Concn
0.10-0.50 ppm
Ref No.
2
Commondity
artichokes, fresh
Concn
>2.0 ppm
Notes
January 1, 1992 and March 31, imported Canadian agricultural commodities
Ref No.
2
Commondity
beets, fresh
Concn
0.1-0.5 ppm
Ref No.
2
Commondity
celery, fresh
Concn
2.0 ppm
Ref No.
2
Commondity
cucumbers, fresh
Concn
0.1-0.5 ppm
Ref No.
2
Commondity
head lettuce, fresh
Concn
2.0 ppm
Ref No.
2
Commondity
pears, fresh
Concn
0.05-0.5 ppm
Ref No.
2
Commondity
peppers, fresh sweet
Concn
2.0 ppm
Ref No.
2
Commondity
spinach, fresh
Concn
0.50 to >2.0 ppm
Ref No.
2
Commondity
tomatoes, fresh
Concn
<0.05-2.0 ppm
Ref No.
2
Commondity
tomato (1 sample)
Concn
0.79 mg/kg
Notes
Ministry of Agriculture of Egypt's Residue Monitoring Program in 1995
Ref No.
3
Commondity
peach (1 sample)
Concn
0.11 mg/kg
Ref No.
3
Commondity
lettuce
Concn
avg, 0.048 ppm; max 1.02 ppm; 3.6% of samples)
Notes
Ministry of Agriculture of Belgium's Total Diet Study between 1991-1993
Ref No.
4
Commondity
peppers
Concn
avg, 0.078 ppm; max, 1.06 ppm; 0.8% of samples
Ref No.
4
Commondity
Lamb's lettuce
Concn
avg, 0.037 ppm; max, 0.75 ppm; 3.0% of samples
Ref No.
4
(1) Neidert W et al; J AOAC Int 77: 18-33 (1994)
(2) Neidert E, Saschenbrecker PW; J AOAC Int 79: 549-66 (1996)
(3) Dogheim SM et al; J AOAC Int 82: 948-54 (1999)
(4) Dejonckheere W et al; J AOAC Int 79: 97-110 (1996)

14.2.19 Plant Concentrations

In a 1986 field study, the average permethrin concentrations found on strawberry flowers or young fruit were 0.637, 0.463, 0.0142, 0.071, 0.039, and 0.015 ppm at 0, 2, 4, 7, 11, and 18 days after treatment, respectively(1); the average concentrations in 1987 were 2.180, 0.090, 0.143, 0.083, 0.089, and 0.027 ppm at 0, 2, 4, 7, 11, and 18 days after treatment, respectively(1). Imported wheat was found to contain permethrin concentrations of 0.014-0.048 ug/g(2).
(1) Belanger A et al; J Environ Sci Health B25: 615-25 (1990)
(2) Riazuddin R et al; Bull Environ Contam Toxicol 87: 303-306 (2011)
Permethrin was not detected at concentrations greater than 10 ug/kg in 182 fish taken from 2 creeks approximately 60-100 m from potato fields where permethrin was applied via aerial spraying(1).
(1) Frank R et al; Environ Monit Assess 16: 137-50 (1991)

14.2.20 Milk Concentrations

Very small amounts /of permethrin/ are distributed into milk in animals.
American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 84:04.12

14.2.21 Other Environmental Concentrations

In a nationwide survey of 1,131 public and private residential homes conducted by the USEPA and US Dept of Housing and Urban Development, permethrin isomers were detected (detection limit of 0.0018-0.0024 ng/sq cm) in 88-89% of 448-459 floor wipe samples collected between June 2005 and March 2006 at a maximum concentrations of 68 (cis-isomer) and 102 (trans-isomer) ng/sq cm and mean concentrations of 1.4 (cis-isomer) and 2.2 (trans-isomer) ng/sq cm(1). Mean surface concentrations of permethrin measured in a variety of residential homes and child care centers ranged from 0.03 to 3.06 ng/sq cm with 68-100% detection frequencies(1). In 2006, two dust samples were collected 5-8 days apart from each of 13 urban homes in Oakland, California and 15 farmworker homes in Salinas, California, an agricultural community (54 samples total)(2); permethrin was detected (detection limit of 4 ng/g) in 100% of samples from the farmworker homes with a concentration range of 45.9-9690 ng/g(2); permethrin was detected in 100% of samples from Oakland homes with a concentration range of 11.6-46800 ng/g(2).
(1) Stout DM et al; Environ Sci Technol 43: 4294-4300 (2009)
(2) Quiros-Alcala L et al; Environ Health 10: 19 (2011). Available from, as of Feb 28, 2014: https://www.ehjournal.net/content/10/1/19

14.2.22 Probable Routes of Human Exposure

Occupational exposure to permethrin may occur through inhalation and dermal contact with this compound at workplaces where permethrin is produced or used(SRC). The EPA has determined that there are potential exposures to mixers, loaders, applicators, and other handlers during usual use-patterns associated with permethrin via inhalation and dermal contact(1,2). In Japan, the concentration of permethrin in the air near a spreader's mouth area was 14.6 ug/cu m during application of the pesticide(3). Monitoring/use data indicate that the general population may be exposed to permethrin via inhalation of ambient air and ingestion of food and drinking water, and dermal contact through the household use of consumer products containing permethrin(SRC).
(1) USEPA; Pyrethrins/Pyrethroid Cumulative Risk Assessment, October 4, 2011; Available, as of Feb 28, 2014: https://www.epa.gov/oppsrrd1/reevaluation/pyrethroids-pyrethrins.html
(2) USEPA/OPPTS; Reregistration Eligibility Decisions (REDs) for Permethrin (Revised May 2009). EPA 738-R-09-306. Available from, as of Mar 3, 2014: https://www.epa.gov/pesticides/reregistration/status.htm
(3) Asakawa F et al; Bull Environ Contam Toxicol 56: 42-49 (1996)
Permethrin has application involving aerial or ground spraying(1). In pesticide formulating plants, exposure to permethrin may be from spillage; furthermore, there is a high potential for exposure at mixing and bagging stations(2). Crop workers may be exposed during application; however, their main exposure results from contact with treated foliage or to pesticide or pesticide-contaminated material made airborn through agitation of foliage during work activity(2). Incidental to treating a crop, some pesticides, such as permethrin, may drift onto workers in neighboring fields or in nearby suburban areas without there being any intent to treat those areas(2). Therefore exposure of the general population to permethrin may occur through inhalation and dermal contact resulting from spraying nearby areas(2).
(1) World Health Org; WHO Specifications and Evaluations for Public Health Pesticides, Permethrin (40:60 cis:trans isomer ratio) (March 2009). Available from, as of Mar 3, 2014: https://www.who.int/whopes/quality/en/Permethrin_specs_eval_WHO_March_2009.pdf
(2) Wolfe HR; pp. 137-63 in Air Pollut Pest and Agric Processes. Lee RI Jr, ed. CRC Press (1976)
According to a pilot investigation of pesticides in 9 homes in Jacksonville, FL during August of 1985, potential respiratory exposure to permethrin was estimated in 1 home using a personal monitor carried by a resident of each household(1).
(1) Lewis RG et al; Environ Monit Assess 10: 59-73 (1988)

14.2.23 Average Daily Intake

The average daily intake (AVDI) of permethrin in 8 population groups in 1982-1984 was determined according to the FDA's monitoring program for chemical contaminants in the U.S. food supply (Total Diet Study or Market Basket Study). In 6-11 month old infants, the AVDI was 1.2 ng/kg-body weight-per day. In 2 yr old toddlers, the AVDI was 5.6 ng/kg-body weight-per day. In 14-16 year old females, the AVDI was 3.3 ng/kg-body weight-per day. In 14-16 year old males, the AVDI was 3.0 ng/kg-body weight-per day. In 25-30 year old females, the AVDI was 5.0 ng/kg-body weight-per day. In 25-30 year old males, the AVDI was 4.1 ng/kg-body weight-per day. In 60-65 year old females, the AVDI was 6.5 ng/kg-body weight-per day. In 60-65 year old males, the AVDI was 5.4 ng/kg-body weight-per day(1).
(1) Gunderson EL; J Assoc Off Anal Chem 71: 1200-9 (1988)
The average daily intake (AVDI) of permethrin (total) in 8 population groups in 1986-1991 was determined according to the FDA's monitoring program for chemical contaminants in the U.S. food supply (Total Diet Study or Market Basket Study). In 6-11 month old infants, the AVDI was 4.7 ng/kg-body weight-per day. In 2 yr old toddlers, the AVDI was 7.1 ng/kg-body weight-per day. In 14-16 year old females, the AVDI was 3.6 ng/kg-body weight-per day. In 14-16 year old males, the AVDI was 4.2 ng/kg-body weight-per day. In 25-30 year old females, the AVDI was 5.7 ng/kg-body weight-per day. In 25-30 year old males, the AVDI was 4.6 ng/kg-body weight-per day. In 60-65 year old females, the AVDI was 5.9 ng/kg-body weight-per day. In 60-65 year old males, the AVDI was 5.9 ng/kg-body weight-per day(1).
(1) FDA; J AOAC Int 76: 127A-148A (1993)
The average daily intake (AVDI) of permethrin (total) in 8 population groups in 1984-1996 was determined according to the FDA's monitoring program for chemical contaminants in the U.S. food supply (Total Diet Study or Market Basket Study). In 6-11 month old infants, the AVDI was 44.1 ng/kg-body weight-per day. In 2 yr old toddlers, the AVDI was 12.8 ng/kg-body weight-per day. In 14-16 year old females, the AVDI was 5.5 ng/kg-body weight-per day. In 14-16 year old males, the AVDI was 7.6 ng/kg-body weight-per day. In 25-30 year old females, the AVDI was 7.7 ng/kg-body weight-per day. In 25-30 year old males, the AVDI was 7.0 ng/kg-body weight-per day. In 60-65 year old females, the AVDI was 12.4 ng/kg-body weight-per day. In 60-65 year old males, the AVDI was 11.5 ng/kg-body weight-per day(1).
(1) Gunderson EL; J AOAC Int 78: 910-21 (1995)

14.2.24 Body Burden

The concentration of permethrin in the urine of an agricultural worker exposed to the pesticide during application to cabbage was 0 (before application), 0 (after application), 1.8 (6 hrs), 2.8 (17 hrs), 1.4 (26 hrs), 1.9(30 hrs), and 1.6 (40 hrs) ng/mg(1). A person who packed conifer seedlings for 6 hrs in a tunnel in Sweden (whose face was close to the plants) excreted 0.26 ug/mL permethrin acid metabolite in the urine the following morning; in the afternoon, excretion was below the detection limit(2).
(1) Asakawa F et al; Bull Environ Contam Toxicol 56: 42-49 (1996)
(2) IARC; IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans 53: 329-49 (1991)

15 Associated Disorders and Diseases

16 Literature

16.1 Consolidated References

16.2 NLM Curated PubMed Citations

16.3 Springer Nature References

16.4 Wiley References

16.5 Chemical Co-Occurrences in Literature

16.6 Chemical-Gene Co-Occurrences in Literature

16.7 Chemical-Disease Co-Occurrences in Literature

17 Patents

17.1 Depositor-Supplied Patent Identifiers

17.2 WIPO PATENTSCOPE

17.3 Chemical Co-Occurrences in Patents

17.4 Chemical-Disease Co-Occurrences in Patents

17.5 Chemical-Gene Co-Occurrences in Patents

18 Interactions and Pathways

18.1 Chemical-Target Interactions

18.2 Drug-Drug Interactions

19 Biological Test Results

19.1 BioAssay Results

20 Taxonomy

21 Classification

21.1 MeSH Tree

21.2 NCI Thesaurus Tree

21.3 ChEBI Ontology

21.4 KEGG: EDC

21.5 KEGG: Pesticides

21.6 KEGG: USP

21.7 KEGG: ATC

21.8 KEGG: Risk Category of Japanese OTC Drugs

21.9 KEGG: OTC drugs

21.10 KEGG: Animal Drugs

21.11 WHO ATC Classification System

21.12 ChemIDplus

21.13 CAMEO Chemicals

21.14 ChEMBL Target Tree

21.15 UN GHS Classification

21.16 EPA CPDat Classification

21.17 NORMAN Suspect List Exchange Classification

21.18 EPA DSSTox Classification

21.19 International Agency for Research on Cancer (IARC) Classification

21.20 Consumer Product Information Database Classification

21.21 FDA Drug Type and Pharmacologic Classification

21.22 EPA Substance Registry Services Tree

21.23 MolGenie Organic Chemistry Ontology

22 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester
    https://services.industrialchemicals.gov.au/search-inventory/
  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. ILO-WHO International Chemical Safety Cards (ICSCs)
  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. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  7. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  8. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  9. EPA Integrated Risk Information System (IRIS)
  10. EPA Safe Drinking Water Act (SDWA)
  11. 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
    m-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.052.771
    m-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (EC: 258-067-9)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/59336
  12. Hazardous Substances Data Bank (HSDB)
  13. 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
  14. 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/
  15. NJDOH RTK Hazardous Substance List
  16. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  17. EU Pesticides Database
  18. California Safe Cosmetics Program (CSCP) Product Database
    Permethrin (including cis- and trans-)
    https://cscpsearch.cdph.ca.gov/search/detailresult/555
  19. 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/
  20. 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
  21. ChEBI
  22. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  23. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  24. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB 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 (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  25. 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
  26. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  27. 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
  28. Therapeutic Target Database (TTD)
  29. DailyMed
  30. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  31. Drugs and Lactation Database (LactMed)
  32. Drugs@FDA
    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
  33. WHO Model Lists of Essential Medicines
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) license.
    https://www.who.int/about/policies/publishing/copyright
  34. EPA Chemical and Products Database (CPDat)
  35. 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/
    PERMETHRIN
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  36. EPA Pesticide Ecotoxicity Database
  37. EPA Regional Screening Levels for Chemical Contaminants at Superfund Sites
  38. EU Clinical Trials Register
  39. USGS Health-Based Screening Levels for Evaluating Water-Quality Data
  40. NITE-CMC
    3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate - FY2006 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/06-imcg-0464e.html
    3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (synonym: Permethrin) - FY2021 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/21-meti-2023e.html
  41. 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
    permethrin (ISO); m-phenoxybenzyl...
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  42. FDA Orange Book
    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
  43. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  44. USGS Columbia Environmental Research Center
  45. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  46. International Agency for Research on Cancer (IARC)
    LICENSE
    Materials made available by IARC/WHO enjoy copyright protection under the Berne Convention for the Protection of Literature and Artistic Works, under other international conventions, and under national laws on copyright and neighbouring rights. IARC exercises copyright over its Materials to make sure that they are used in accordance with the Agency's principles. All rights are reserved.
    https://publications.iarc.fr/Terms-Of-Use
    IARC Classification
    https://www.iarc.fr/
  47. Japan Chemical Substance Dictionary (Nikkaji)
  48. 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
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    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
  49. MassBank Europe
  50. 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
  51. Metabolomics Workbench
  52. National Drug Code (NDC) Directory
    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
  53. Natural Product Activity and Species Source (NPASS)
  54. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  55. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  56. SpectraBase
    trans-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid, 3-phenoxy-benzyl ester
    https://spectrabase.com/spectrum/17yCiV8hTs2
    cis-3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid, 3-phenoxy-benzyl ester
    https://spectrabase.com/spectrum/Er9P39Ws5Lp
  57. Springer Nature
  58. Wikidata
  59. Wikipedia
  60. Wiley
  61. 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
  62. PubChem
  63. GHS Classification (UNECE)
  64. EPA Substance Registry Services
  65. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  66. PATENTSCOPE (WIPO)
  67. NCBI
CONTENTS