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beta-cypermethrin (Ref: OMS 3068)
** beta-cipermetrin ** cypermethrinbeta ** Translations

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

SUMMARY

A pyrethroid insecticide currently within the EU regulatory review process. It has a low aqueous solubility, in relatively volatile and, based on its chemical properties, is not expected to leach to groundwater. It is non-persistent in soil systems. It is highly toxic to mammals and there is some concern regarding its ability to bioconcentrate. It is moderately toxic to birds, earthworms and highly toxic to honey bees and most aquatic species except for algae where there is a reduced risk.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for beta-cypermethrin

Description: A broad spectrum insecticide used to control common pests in crops, public health and veterinary situations.

Example pests controlled: Aphids; Cockroaches; Fleas; Ticks; Flies; Mosquitoes

Example applications: Oilseed rape; Wheat; Barley; Maize; Livestock; Public health situations

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1989

EC Regulation 1107/2009 (repealing 91/414):
Status Not approved
Dossier rapporteur/co-rapporteur United Kingdom
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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism Cypermethrin is a chiral molecule and consists of eight isomers, four cis and four trans. Beta -cypermethirn is a reaction mixture of two enantiomeric forms.
Chemical formula C22H19Cl2NO3
Canonical SMILES CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
Isomeric SMILES CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
International Chemical Identifier key (InChIKey) GUQZCTLEJXHSIH-RZAVTOELSA-N
International Chemical Identifier (InChI) InChI=1S/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/t17-,18+,20-/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 >960mg/kg
Known relevant impurities EU dossier: none declared
Substance origin Synthetic
Mode of action Non-systemic with contact and stomach action. Sodium channel modulator.
CAS RN 65731-84-2
EC number 265-898-0
CIPAC number 632
US EPA chemical code 109702
PubChem CID 6455379
Molecular mass (g mol-1) 416.3
PIN (Preferred Identification Name) reaction mixture comprising the enantiomeric pair rac-(R)-cyano(3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate in ratio approximately 2:3 with the enantiomeric pair rac-(R)-cyano(3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
IUPAC name (R)-α-cyano-3-phenoxybenzyl (1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (S)-α-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CAS name cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Other status information -
Relevant Environmental Water Quality Standards UK Environment Agency non-statutory standard for the protection of aquatic life in freshwater and saltwater annual average 0.0002 ug/L, max acceptable conc 0.002 ug/L
UK statutory standard for water quality: ‘Good’ for fresh, transitional & saltwater: 0.1 ng/L as annual mean conc, 0.4 ng/L 95th percentile
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 Musca domestica
Triatoma infestans
Physical state White powder
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
  • Bonide Products
  • Syngenta
  • NuFarm
Example products using this active
  • Cymbush 3E Insecticide
  • Siperin
  • Barricade
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Usually supplied as an emulsifiable concentrate.


ENVIRONMENTAL FATE

for beta-cypermethrin

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) 0.9 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 14000 A5 - n-Heptane -
45000 A5 - Methanol -
26000 A5 - Octanol -
1000000 A5 - Ethyl acetate -
Melting point (oC) 63 A5 -
Boiling point (oC) 253 A5 - Decomposes -
Degradation point (oC) 253 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 6.31 X 1005 Calculated -
Log P 5.8 A5 High
Bulk density (g ml-1)/Specific gravity 1.34 L3 -
Dissociation constant (pKa) at 25oC n/d A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.02 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 9.1 X 10-08 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index -1.52 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 Acidic: 204nm=44881, 277nm=714
Neutral: 203nm-61241
Basic: 208nm=39764, 310nm=2756
A5 -
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) 27.1 A5 Non-persistent
DT50 (lab at 20oC) 27.1 A5 Non-persistent
DT50 (field) - - -
DT90 (lab at 20oC) - - -
DT90 (field) - - -
DT50 modelling endpoint - - -
Note EU dossier DT50 lab studies range 15.2-43.4 days days ; DT90 range 257-734 days
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value 4.9 R4 -
Note Published literature RL50 range 3.7-6.0 days, 2 field crops, various matrices, n=2
Aqueous photolysis DT50 (days) at pH 7 Value - - -
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value - - -
Note -
Water-sediment DT50 (days) 22.2 A5 Fast
Water phase only DT50 (days) - - -

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 - - -
Koc -
Notes and range -
Freundlich Kf 1369 A5 Non-mobile
Kfoc 114676
1/n 1.001
Notes and range EU dossier Kf range 889-1622 mL/g, Kfoc range 41167-249607 mL/g, 1/n range 0.946-1.072, Soils=4
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
3-phenoxybenzoic acid This metabolite may cause environmental pollution, click here for further information Soil   0.171   Major fraction; Relevant
3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate This metabolite may cause environmental pollution, click here for further information Soil   0.271   Major fraction; Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
3-phenoxybenzaldehyde - Aqueous and soil photolysis - -
3-phenoxybenzylactetic acid - Aqueous photolysis - -
Phenol - Aqueous photolysis - -
Cyperamide - Aqueous and soil photolysis; Hydrolysis - -
alpha-carbamoyl-3-phenoxybenzyl-alcohol - Soil photolysis - -
2-OH-PBAcid - - - -
PBAlcohol - - - -
N-(3-phenoxybenzoyl)glycerine - - - -
N-(3-phenoxybenzoyl)glutamic acid - - - -
3-(4-hydroxyphenoxy)benzoic acid O-sulfate - - - -
taurine-PBA - Mouse - -


ECOTOXICOLOGY

for beta-cypermethrin

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) 846 A5 Threshold for concern
CT50 (days) 2.0 -
Mammals - Acute oral LD50 (mg kg-1) 93.0 A5 Rat High
Mammals - Short term dietary NOEL (mg kg-1) - L3 Rat -
(ppm diet) > 250 -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Collinus virginians Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.00039 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.00037 A5 Pimephales promelas, 34 days High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.00042 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) - - -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.0000059 A5 Mysidopsis 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) 0.00006 A5 Chironomus riparius High
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) - - -
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) > 0.053 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) 0.014 A5 High
Oral acute 48 hour LD50 (μg bee-1) 0.05 A5 High
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 150 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 0.243 A5 Eisenia foetida, corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 100 Mortality,
Dose 12.5g ha-1
A5 Aphidius rhopalosiphi
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 100 Mortality,
Dose 12.5g ha-1
A5 Typhlodromus pyri
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 0.67mg kg-1, 28days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for beta-cypermethrin

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) 93.0 A5 Rat High
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 1.06 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.0016 A5 Dog, SF=300 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.0016 A5 Dog, SF=300 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.0008 A5 Dog, SF=600 -
Dermal penetration studies (%) 5-7 A5 Concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Risk from vapour exposure risk identified for bystanders in the vicinity
Occupational PPE/PPC required to reduce exposure risk
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
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 Risk of serious damage to the eye

: 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 class 6.1
Not explosive or oxidising
CLP classification 2013 Health: H301, H318, H332, H335
Environment: H410
EC Risk Classification Click here to view information omn the EU risk phrases T - Toxic: R25
Xn - Harmful: R20, R41
Xi - Irritant: R37
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S22, S26, S39, S60, S61
WHO Classification NL - Not listed
US EPA Classification (formulation) - -
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for beta-cypermethrin

Language Name
English beta-cypermethrin
French betacypermethrine
German beta-Cypermethrin
Danish betacypermethrin
Italian beta-cipermetrina
Spanish beta-cipermetrina
Greek -
Slovenian beta-cipermetrin
Polish beta-cypermetryna
Swedish -
Hungarian beta-cypermethrin
Dutch -

Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk