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permethrin (Ref: OMS 1821)
** permethrine ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
Further data may be found in the VSDB

SUMMARY

Permethrin is a contact insecticide that is not approved for use in the EU. It is not highly soluble in water, has a low volatility and is not normally expected to leach to groundwater. It would also not be expected to persist in soil or water systems. It is moderately toxic to humans, is an irritant and may be a CNS toxicant. It is highly toxic to most aquatic species and honey bees but is not highly toxic to birds or earthworms.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for permethrin

Description: An insecticide active against a wide range of pests including Lepidoptera and Coleoptera in crops and various animal ectoparasites

Example pests controlled: Cockroaches; Termites; Ticks; Mosquitoes; Aphids; Fleas; Ants

Example applications: Fruit; Vegetables; Cotton; Ornamentals; Potatoes; Cereals

Efficacy & activity: -

Availability status: Current

Introduction & key dates: circa 1973

EC Regulation 1107/2009 (repealing 91/414):
Status Not approved
Dossier rapporteur/co-rapporteur Ireland
Date inclusion expires Expired
EU Candidate for substitution (CfS) Not applicable
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism A chiral molecule
Chemical formula C21H20Cl2O3
Canonical SMILES CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) RLLPVAHGXHCWKJ-UHFFFAOYSA-N
International Chemical Identifier (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/t17-,19-/m0/s1
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Insecticide, Veterinary substance
Substance group Pyrethroid
Minimum active substance purity -
Known relevant impurities -
Substance origin Synthetic
Mode of action Broad spectrum with contact and stomach action. Slight repellant effect. Sodium channel modulator.
CAS RN 52645-53-1
EC number 258-067-9
CIPAC number 331
US EPA chemical code 109701
PubChem CID 40326
Molecular mass (g mol-1) 391.3
PIN (Preferred Identification Name) -
IUPAC name 3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CAS name (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Other status information Chemical subject to PIC regulations
Relevant Environmental Water Quality Standards UK statutory standard for the protection of aquatic life: freshwater and saltwater: 0.01 ug/L
Herbicide Resistance Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) 3
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Aedes aegypti
Bemisia tabaci
Chrysoperla carnea
Culex pipiens pipiens
Diadegma insulare
Helicoverpa zea
many others
Physical state Colourless crystalline solid to brown viscous liquid depending upon purity
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Agropharm
  • ICI Plant Protection
  • Mitchell Cotts
  • FMC
Example products using this active
  • Fortefog P Fumer
  • Ambush
  • Exmin
  • Kestril
  • Ectiban
  • Pynosect
  • Corsair
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Available in a variety of formulations including fumigants, shampoos and spot-on treatments.


ENVIRONMENTAL FATE

for permethrin

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 0.2 G4 Low
Solubility - In organic solvents at 20oC (mg l-1) 1000000 L3 - Hexane -
258000 L3 - Methanol -
1000000 L3 - Xylene -
Melting point (oC) 34.5 E3 -
Boiling point (oC) 200 E3 -
Degradation point (oC) - - -
Flashpoint (oC) 100 L3 -
Octanol-water partition coefficient at pH 7, 20oC P 1.26 X 1006 Calculated -
Log P 6.1 G4 High
Bulk density (g ml-1)/Specific gravity 1.29 L3 -
Dissociation constant (pKa) at 25oC - - -
Note:
Vapour pressure at 20oC (mPa) 0.007 R4 - @25DegC Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.89 X 10-01 H4 Moderately volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index -1.11 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 5.35 X 10-03 Calculated -
Note Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 - - -
Surface tension (mN m-1) - - -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 13 K4 Non-persistent
DT50 (lab at 20oC) 13 K4 Non-persistent
DT50 (field) 42 H4 Moderately persistent
DT90 (lab at 20oC) - - -
DT90 (field) - - -
DT50 modelling endpoint - - -
Note: -
Dissipation rate RL50 on plant matrix Value 6.7 R4 -
Note Published literature RL50 range 2.5-20.0 days, 8 field & undercover grown crops, various matrices, n=9
Dissipation rate RL50 on and in plant matrix Value 11.1 R4 -
Note Published literature RL50 range 9.5-13.9 days, 3 field & undercover grown crops, various matrices, n=3
Aqueous photolysis DT50 (days) at pH 7 Value 1 K4 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 31 K4 Moderately persistent
Note -
Water-sediment DT50 (days) 40 K4 Moderately fast
Water phase only DT50 (days) 23 K4 Slow

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - G4 Non-mobile
Koc 100000
Notes and range -
Freundlich Kf 1.87 R4 -
Kfoc -
1/n 0.99
Notes and range Soil with 68% loam, 24% silt, 8% clay, pH 6.5, OC=2.1%
pH sensitivity -


ECOTOXICOLOGY

for permethrin

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 300 P4 (Other literature Log BCF range 1.4-3.3 (R3)) Threshold for concern
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) > 430 G4 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) - L2 Rat, 2 year -
(ppm diet) 100 -
Birds - Acute LD50 (mg kg-1) > 9800 G4 Anas platyrhynchos Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.0125 G4 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.00012 Q2 Unknown species High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.0006 E3 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) - - -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.00002 F3 Americamysis bahia High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) 0.0029 F4 Chironomus riparius High
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) - - -
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.0125 K3 Unknown species Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.0009 Q2 Unknown species High
Honeybees Contact acute 48 hour LD50 (μg bee-1) 0.024 F4 Apis mellifera High
Oral acute 48 hour LD50 (μg bee-1) 0.13 F4 Apis mellifera High
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 1440 Q3 Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect Harmful Q2 Parasitoids -
Other arthropod (2) LR50 g ha-1 - - -
% Effect Harmful AA2 Typhlodromus pyri -
Soil micro-organisms - - -
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for permethrin

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 430 G4 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 F4 Rabbit -
Mammals - Inhalation LC50 (mg l-1) > 0.685 L3 Rat -
Other Mammal toxicity endpoints Intraperitoneal LD50 = 429 mg kg-1 V3 Mouse -
Intravenous LD50 = 31.0 mg kg-1 V3 Mouse -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.05 JMPR 1999 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 1.5 JMPR 2003 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) - - -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public -
Occupational -
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards Non-statutory WHO drinking water guideline 0.3 mg/L UK EA QS database, 2018 -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

-

General human health issues Harmful
Estrogenic
IARC Group 3 carcinogen; USEPA - probable human carcinogen
Endocrine issues - Inhibition of estrogen-sensitive cells proliferation

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes IMDG Transport Code is usually 6.1
CLP classification 2013 Health: H302, H332, H335
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R20/22, R43
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S13, S24, S36/37/39, S60, S61
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II, III - Warning - Moderately toxic, Caution - Slightly toxic
UN Number 3352 for active, products usually 1230
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (medium danger)


TRANSLATIONS

for permethrin

Language Name
English permethrin
French permethrine
German Permethrin
Danish permethrin
Italian permetrina
Spanish permetrin
Greek permethrin
Slovenian permetrin
Polish permetryna
Swedish permetrin
Hungarian permetrin
Dutch permethrin

Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk