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

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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
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)	-
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

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

General status:

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
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
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	kaolin

Formulations:

Property	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		Value	Source/Quality Score/Other Information	Interpretation
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		-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	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		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		-	-	-
Surface tension (mN m-1)		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (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		Value	Source/Quality Score/Other Information	Interpretation
General		IMDG Transport Code is usually 6.1
CLP classification 2013		Health: H302, H332, H335 Environment: H400, H410
EC Risk Classification		Xn - Harmful: R20/22, R43 N - Dangerous for the environment: R50, R53
EC Safety Classification		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		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

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Record last updated: Friday 15 June 2018
Contact: aeru@herts.ac.uk