Beta-cypermethrin (Ref: OMS 3068)

Beta-cypermethrin (Ref: OMS 3068)	Last updated: 05/01/2021
(Also known as: beta-cipermetrin ; cypermethrinbeta)

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

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

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

United Kingdom

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece

ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg

LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia

Also used in

Australia

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)

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

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
beta-cypermethrin	-

General status

Pesticide type

Insecticide, Veterinary substance

Substance group

Pyrethroid

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.

CAS RN

65731-84-2

EC number

265-898-0

CIPAC number

632

US EPA chemical code

109702

PubChem CID

6455379

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

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Musca domestica, Triatoma infestans

Physical state

White powder

Related substances & organisms

alpha-cypermethrin

cypermethrin

zeta-cypermethrin

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Cymbush 3E Insecticide
Siperin
Barricade

Example products using this active

Bonide Products
Syngenta
NuFarm

Formulation and application details

Usually supplied as an emulsifiable concentrate

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)

Not expected to self ignite; Not highly flammable

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

6.31 X 10⁰⁵

Calculated

Log P

5.8

High

Bulk 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

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)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

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)

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

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 20 °C and pH 7

Value

Note

Water-sediment DT₅₀ (days)

22.2

Fast

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

1369

Non-mobile

K_foc

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

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

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

3-phenoxybenzoic acid

Soil

0.171

Major fraction; Relevant

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

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

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

846

Threshold for concern

CT₅₀ (days)

2.0

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

Collinus virginians

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00039

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00037

Pimephales promelas 34 day

High

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

0.00042

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (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)

Non-target plants

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

> 0.053

Pseudokirchneriella subcapitata

Moderate

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

Honeybees (Apis spp.)

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

0.014

High

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

0.05

High

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

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 pollinators (1)

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

Mode of exposure

Other pollinators (2)

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

Mode of exposure

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

100

Mortality, [Dose 12.5g ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

100

Mortality, [Dose 12.5g ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 0.67mg kg⁻¹ 28days

Mesocosm study data

NOEAEC mg l⁻¹

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

Dog SF=300

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

0.0016

Dog SF=300

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

Dog SF=600

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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 class 6.1
Not explosive or oxidising

CLP classification 2013

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

EC Risk Classification

T - Toxic: R25
Xn - Harmful: R20, R41
Xi - Irritant: R37
N - Dangerous for the environment: R50, R53

EC Safety Classification

S22, S26, S39, S60, S61

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

Packaging Group III (minor danger)

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

Record last updated:	05/01/2021
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