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cypermethrin (Ref: OMS 2002)
** cypermethrine ** Translations

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

SUMMARY

Cypermethrin is an insecticide that has approval for use in the EU. It has a low aqueous solubility and is non-volatile. Whilst its chemical properties suggest that it should not leach to groundwater it has been found to pollute some groundwater bodies. It is considered a serious marine pollutant. It is moderately persistent is soils but is likley to degrade moderately fast in water systems under day light conditions. It is moderately toxic to mammals and their is some concern regarding its potential to bioaccumulate. Whilst it is an irritant no serious human health issues have been identified. It is highly toxic to most aquatic species and honeybees. it is moderately toxic to earthworms but there is little risk to birds.

GENERAL INFORMATION
for cypermethrin

Description: An insecticide used to control a broad spectrum of pests especially Lepidoptera

Introduction: 1975, first reported

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Belgium
Date inclusion expires 28/02/2016

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia, USA

General status:
Pesticide type Insecticide, Veterinary Treatment
Substance group Pyrethroid
Substance origin Synthetic
Mode of action Non-systemic with contact and stomach action. Sodium channel modulator.
CAS RN 52315-07-8
EC number 257-842-9
CIPAC number 332
US EPA chemical code 109702/129064
Chiral molecule Chiral or specific isomer of chiral molecule
Chemical formula C22H19Cl2NO3
SMILES Cl/C(Cl)=C/C3C(C(=O)OC(C#N)c2cccc(Oc1ccccc1)c2)C3(C)C
International Chemical Identifier (InChI) InChI=1/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3
Structure diagram/image available? Yes
Molecular mass (g mol-1) 416.3
PIN (Preferred Identification Name) (E)-cyano(3-phenoxyphenyl)methyl (1E,3E)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
IUPAC name (RS)-α-cyano-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CAS name cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Other status information Severe Marine Pollutant, Surface and Groundwater Pollutant
Herbicide Resistance Classification (HRAC) Not applicable
Insecticide Resistance Classification (IRAC) 3
Fungicide Resistance Classification (FRAC) Not applicable
Physical state Liquid
Related substances & organisms

Formulations:
Property Value
Example manufacturers of products using this active
  • AgriGuard
  • Fargro
  • Nufarm
Example products using this active
  • Permasect C
UK LERAP status LERAP Category A, Broadcast Air Assisted LERAP
Formulation and application details Often supplied as an emulsifiable concentrate which is mixed with water and applied as a spray for crop use and in topically applied formulations for animals.


ENVIRONMENTAL FATE

for cypermethrin

Property Value Source/Quality Score/Other Information Interpretation
Solubility - In water at 20oC (mg l-1) 0.009 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 2000000 A5 - Ethyl acetate -
450000 A5 - Acetone -
450000 A5 - Methanol -
142000 A5 - Hexane -
Melting point (oC) 41.2 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) - - -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 2.00 X 1005 Calculated -
Log P 5.3 A5 High
Bulk density (g ml-1)/Specific gravity 1.3 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 25oC (mPa) 0.00023 A5 Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) 2.00 X 10-02 L3 Non-volatile
Henry's law constant at 20oC (dimensionless) 3.70 X 10-06 K3 Moderately volatile
GUS leaching potential index -2.12 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 High
Maximum UV-vis absorption L mol-1 cm-1 204nm = 43217, 278nm = 2368 A5 -
Surface tension (mN m-1) - - -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 60 K4 Moderately persistent
DT50 (lab at 20oC) 68 A5 Moderately persistent
DT50 (field) 69 A5 Moderately persistent
DT90 (lab at 20oC) 273 A5 -
DT90 (field) 126 A5 -
Note EU dossier Lab studies DT50 (1) cis-isomer 31-107 days (2) trans-isomer 13-58 days, DT90 (1) cis-isomer 102-792 days (2) trans-isomer 69-251 days; field studies DT50 range 14-199 days, DT90 range 28-375 days
Aqueous photolysis DT50 (days) at pH 7 Value 13 A4 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 179 A3 Persistent
Note pH sensitive and varies with isomer: stable pH 3 to pH 7, DT50 21.2 days pH 8 cis-isomer, 9.1 days pH 8 trans-isomer, ~30 mins at pH 11.
Water-sediment DT50 (days) 17 A5 Fast
Water phase only DT50 (days) 3 A5 Moderately fast

Soil adsorption and mobility:
Property Value Source/Quality Score/Other Information Interpretation
Linear Kd 1875 A4 Non-mobile
Koc 156250
Notes and range EU dossier see alpha cypermethrin for more data
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity -

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy
3-phenoxybenzoic acid Clay soil   0.480   Major fraction, Not relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
3-(4-hydroxyphenoxy)benzoic acid 4'HO3PBA Soil - -
4-hydroxycypermethrin - Soil; Animal - -
3-(2,2-dichloroethenyl(-2,2-dimethyl cyclopropane carboxylic acid (cis- and trans-) - Soil (Aerobic) - -
3-phenoxybenzoic acid
(Ref: )
Note: Major fraction, Not relevant
- Soil (Aerobic) - -
(RS)-Carbamoyl(3-phenoxyphenyl)-methyl (1RS)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate - Soil - -
3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid
(Ref: )
Note: Major fraction, Not relevant
- Soil (Photolysis) - -


ECOTOXICOLOGY

for cypermethrin

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF 1204 A5 Threshold for concern
CT50 (days) Not available -
Bioaccumulation potential - Calculated High
Mammals - Acute oral LD50 (mg kg-1) 287 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) 7.5 L2 Rat, 2 year High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 10000 A5 Anas platyrhynchos Low
Birds - Short term dietary (LC50/LD50) > 5620 mg kg feed-1 A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 0.0028 A5 Salmo gairdneri High
Fish - Chronic 21 day NOEC (mg l-1) 0.00003 A4 Pimephales promelas, 34 day -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.0003 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.00004 A5 Daphnia magna -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.0128 F3 Americamysis bahia High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
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) - - -
Algae - Acute 72 hour EC50, growth (mg l-1) > 0.1 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) 1.3 Q2 Unknown species Low
Honeybees - Acute 48 hour LD50 (μg bee-1) 0.02 A5 Contact High
Earthworms - Acute 14 day LC50 (mg kg-1) > 100 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect 16.0 A5 Folsomia candida, 21 day EC50 Mortality mg kg-1 -
Other arthropod (1) LR50 g ha-1 - - -
% Effect Harmful AA2 Typhlodromus pyri Harmful
Other arthropod (2) LR50 g ha-1 - - -
% Effect Moderately harmful AA2 Chrysoperla carnea Moderately harmful
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.15 kg ha-1; 28 days
-
Mesocosm study data NOEAEC mg l-1 0.00005 A5 Aquatic invertebrates and algae -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for cypermethrin

General:
Property Value Source/Quality Score/Other Information Interpretation
Mammals - Acute oral LD50 (mg kg-1) 287 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 3.28 A5 Rat -
Other Mammal toxicity endpoints Intraperitoneal LD50 = 404 mg kg-1 V3 Rat -
Intravenous LDLo = 6.0 mg kg-1 V3 Rat -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.05 A5 Rat, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.2 A5 Rat, SF=100 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.06 A5 -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public -
Occupational -
Examples of European MRLs (mg kg-1) Value Lettuce, citrus, apricots, nectarines and peaches: 2.0; Pomes, cherries and plums: 1.0; Brassicas, peas (with pods), beans (with pods), canefruit and grapes: 0.5; Curcubits, barley and oat grains: 0.2; Asparugus, onions and garlic: 0.1; Other vegetables, other fruit and other cereal grains: 0.05
Note Current May 2007.
For the EU pesticides database click here
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

General human health issues Highly toxic

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

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General Not explosive
IMDG Transport Code is variable depending upon product, often either 3 or 9
CLP classification 2013 Warning: H302; H332; H335
Environment: H400, H410
EC Risk Classification T - Toxic: R22
Xn - Harmful: R48/22
Xi - Irritant: R37
N - Dangerous for the environment: R50, R53 Note: for cis/trans ratio 40:60
EC Safety Classification S1/2, S36/37/39, S45, S60, S61
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II - Warning - Moderately toxic
UN Number 3352 as active, variable with product, usually 1993, 3082 or 3295
Waste disposal & packaging Packaging Group III (minor danger)


TRANSLATIONS

for cypermethrin

Language Name
English cypermethrin
French cypermethrine
German Cypermethrin
Danish cypermethrin
Italian cipermetrina
Spanish cipermetrin
Greek -
Slovenian cipermetrin
Polish cypermetryna
Swedish cypermetrin
Hungarian cypermethrin
Dutch cypermetrine

Record last updated: Monday 30 June 2014
Contact: aeru@herts.ac.uk