Beta-cypermethrin (Ref: OMS 3068)

Beta-cypermethrin (Ref: OMS 3068)	Last updated: 15/03/2024
(Also known as: beta-cipermetrin ; cypermethrinbeta)

SUMMARY

A pyrethroid broad-spectrum insecticide. 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 honeybees and most aquatic species except for algae where there is a reduced risk.

GENERAL INFORMATION

Description

Pyrethroid ester insecticide which is no longer used in veterinary medicine

Availability status

Current

Introduction & key dates

1989, introduced

Examples of veterinary uses

Used to control ectoparasites such as flies ticks and lice

Examples of species treated

Cattle

Approval status

VMR 2013/2033 approval status (GB/UK)

Not approved

EU Regulatory approval status

Not approved

Chemical structure

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)

KAATUXNTWXVJKI-NSHGMRRFSA-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

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
beta-cypermethrin	-

General status

Veterinary substance type

Antiparasitic

Substance groups

Pyrethroid ester insecticide

Minimum active substance purity

>960mg kg⁻¹

Known relevant impurities

EU dossier: none declared

Substance origin

Synthetic

Mode of action

Non-systemic with contact and stomach action. Sodium channel modulator.

Molecular targets

[Sodium channel, Modulator]

CAS RN

65731-84-2

Alternative/old CAS RN

1224510-29-5

EC number

265-898-0

CIPAC number

632

US EPA chemical code

109702

PubChem CID

93357

CLP index number

No data found

Therapeutic Class

Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents

ATCvet Code

QP53AC08

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

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 µg l⁻¹, max acceptable conc 0.002 µg l⁻¹
UK statutory standard for water quality: ‘Good’ for fresh, transitional & saltwater: 0.1 ng l⁻¹ as annual mean conc, 0.4 ng l⁻¹ 95th percentile

Physical state

White powder

Related substances & organisms

cypermethrin

alpha-cypermethrin

theta-cypermethrin

zeta-cypermethrin

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.9

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

14000

n-Heptane

45000

Methanol

26000

Octanol

1000000

Ethyl acetate

Melting point (°C)

Boiling point (°C)

253

Decomposes

Degradation point (°C)

253

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

6.31 X 10⁰⁵

Calculated

Log P

5.8

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies, residues measured in fat of lactating cow

Density (g ml⁻¹)

1.34

Dissociation constant pKa) at 25 °C

n/d

No dissociation

Vapour pressure at 20 °C (mPa)

0.02

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

9.1 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Acidic: 204nm=44881, 277nm=714
Neutral: 203nm-61241
Basic: 208nm=39764, 310nm=2756

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

27.1

Non-persistent

DT₅₀ (lab at 20 °C)

27.1

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

EU dossier DT₅₀ lab studies range 15.2-43.4 days days ; DT₉₀ range 257-734 days

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Note

Water-sediment DT₅₀ (days)

22.2

Fast

Water phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

1369

Non-mobile

K_foc (mL g⁻¹)

114676

¹/_n

1.001

Notes and range

EU dossier K_f range 889-1622 mL g⁻¹, K_foc range 41167-249607 mL g⁻¹, ¹/_n range 0.946-1.072, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.52

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

846

Threshold for concern

CT₅₀ (days)

2.0

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate

Major fraction

0.271

alpha-carbamoyl-3-phenoxybenzyl-alcohol

Photolysis

3-phenoxybenzaldehyde

Photolysis

cyperamide

Photolysis

3-phenoxybenzoic acid

Major fraction

0.171

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate

CPA

Surface water; Sediment

3-phenoxybenzoic acid

Surface water (Photolysis)

3-phenoxybenzoic acid

PBA

Mammal; Surface water; Sediment

2-OH-PBAcid

PBAlcohol

N-(3-phenoxybenzoyl)glycerine

N-(3-phenoxybenzoyl)glutamic acid

Animal

3-(4-hydroxyphenoxy)benzoic acid O-sulfate

taurine-PBA

Mouse

Phenol

Surface water (Photolysis)

cyperamide

Surface water

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

93.0

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

> 250

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 150

Eisenia foetida corr

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

0.243

Eisenia foetida corr

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 0.67 mg kg⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.014

Apis mellifera

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.05

Apis mellifera

High

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) as % Mortality at dose 3.74 g ha⁻¹

33.8

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as % Mortality at dose 12.5 g ha⁻¹

100

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as % Mortality at dose 12.5 g ha⁻¹

100

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00039

Oncorhynchus mykiss

High

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00037

Pimephales promelas 34 day

High

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.00042

Daphnia magna

High

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0000059

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

Chironomus riparius

High

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 0.053

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

93.0

Rat

High

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.06

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.0016

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.0016

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.0008

Dermal penetration studies (%)

5-7

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Risk from vapour exposure risk identified for bystanders in the vicinity

Occupational

PPE/PPC required to reduce exposure risk

Mammalian dose elimination route and rate

Eliminated via the urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Risk of serious damage to the eye

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 9
Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H301, H318, H332, H335
Environment: H410

WHO Classification

Not listed (Not listed)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

beta-cypermethrin

French

betacypermethrine

German

beta-Cypermethrin

Danish

betacypermethrin

Italian

beta-cipermetrina

Spanish

beta-cipermetrina

Greek

Polish

beta-cypermetryna

Swedish

Hungarian

beta-cypermethrin

Dutch

Norwegian

Record last updated:	15/03/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242