Beta-cyfluthrin (Ref: OMS 3051)

Beta-cyfluthrin (Ref: OMS 3051)	Last updated: 13/01/2021
(Also known as: FCR 4545)

SUMMARY

Beta-cyfluthrin is a pyrethroid insecticide approved for use in the EU. It has a low aqueous solubility, semi-volatile and is not expected to leach to groundwater. It is highly toxic to mammals and may be a neurotoxin. It is also highly toxic to fish, aquatic invertebrates, aquatic plants and honeybees but slightly less toxic to birds, algae and earthworms.

GENERAL INFORMATION

Description

A pyrethroid insecticide effective against a range of common pests including locusts in a many different crops

Example pests controlled

Migratory locusts; Grasshoppers; Mosquitoes; Bedbugs; Loopers; Cutworms; Spittlebugs; Leaf hoppers; Caterpillars; Armyworms; Weevils; Stinkbugs

Example applications

Alfalfa; Corn; Cotton; Peanuts; Sorghum; Sugarcane; Sugarbeet; Tobacco; Wheat; Brassicas; Sweetcorn; Potatoes; Tomatoes; Stone fruit; Root vegetables

Efficacy & activity

Field trials have adequately demonstrated efficiacy.

Availability status

Current

Introduction & key dates

1993, first reported

UK regulatory status

UK COPR regulatory status

Phasing out

Date COPR inclusion expires

Expired

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Germany/Hungary

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

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, USA

Chemical structure

Isomerism

An isomeric mixture of the two biologically active diastereoisomeric pairs of cyfluthrin. Diastereomer II 300-400 g/kg; Diastereomer IV 570-670 g/kg.

Chemical formula

C₂₂H₁₈Cl₂FNO₃

Canonical SMILES

CC1(C(C1C(=O)OC(C#N)C2=CC(=C(C=C2)F)OC3=CC=CC=C3)C=C(Cl)Cl)C

Isomeric SMILES

CC1([C@H](C1C=C(Cl)Cl)C(=O)O[C@@H](C#N)C2=CC(=C(C=C2)F)OC3=CC=CC=C3)C

International Chemical Identifier key (InChIKey)

OFHFONYRMVKULH-WNYJFNBPSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance group

Pyrethroid

Minimum active substance purity

>=965 g 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

1820573-27-0

EC number

269-855-7

CIPAC number

482

US EPA chemical code

118831

PubChem CID

56608859

Molecular mass

434.29

PIN (Preferred Identification Name)

reaction mixture comprising the enantiomeric pair rac-(R)-cyano(4-fluoro-3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate in ratio 1:2 with the enantiomeric pair rac-(R)-cyano(4-fluoro-3-phenoxyphenyl)methyl (1S,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

IUPAC name

(R)-α-cyano-4-fluoro-3-phenoxybenzyl (1S,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate and (S)-α-cyano-4-fluoro-3-phenoxybenzyl (1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarbox

CAS name

cyano(4-fluoro-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 freshwater and saltwater aquatic life 0.001 µg l⁻¹

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

Helicoverpa armigera, Musca domestica, Triatoma infestans

Physical state

White crystalline powder

Related substances & organisms

clothianidin

imidacloprid

Formulations

Property

Value

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

Chinook Blue
Modesto
Hawk
Acilothrin B
Bulldog 25EC
Baythroid

Example products using this active

Bayer CropScience
Bayer Environmental Science
AgroCare

Formulation and application details

Available in a wide variety of formulations including emulsifiable concentrates, granules, oil in water emulsions, suspension concentrates, ULVs and wettable powders.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.0019

(isomer mean)

Low

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

150000

Toluene

10000

n-Hexane

200000

Dichloromethane

Melting point (°C)

(82-96 °C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

210

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

7.08 X 10⁰⁵

Calculated

Log P

5.85

(isomer mean)

High

Bulk density (g ml⁻¹)

1.35

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

2.8 X 10^-05

(isomer mean)

Low volatility

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

0.347

(isomer mean)

Moderately volatile

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

ISOMER II Neutral pH; 204nm=41366, 269nm=2129, 276nm=2008, 291nm=80
Acidic pH: 203nm=44498, 269nm=2129, 276nm=2008, 291nm=80
Basic pH: 220nm=29639, 295nm=1486 ISOMER IV Neutral pH 204nm=42545, 269nm=2127, 276nm=2000, 291nm=85
Acidic pH: 204nm=42503, 269nm=2042, 276nm=1957, 291nm=43
Basic pH: 219nm=28888, 294nm=1617

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

28.0

Non-persistent

DT₅₀ (lab at 20 °C)

28.0

Non-persistent

DT₅₀ (field)

93.3

Moderately persistent

DT₉₀ (lab at 20 °C)

677

Very persistent

DT₉₀ (field)

192

DT₅₀ modelling endpoint

Note

EU 2018 Dossier lab studies DT₅₀ (normalised) range 16.7-89.5 days, DT₉₀ (measured) range 66-194 days, Soils =4, Field studies DT₅₀ (measured) range 3.3-297 days, DT₉₀ (measured) range 52-359 days, Soils=4; EU 2002 Dossier Lab studies DT₅₀ range 4-54 days, DT₉₀ range 53-1664 days, field study DT₅₀ range 5-21 days (Germany), DT₉₀ range 70-133 days

Dissipation rate RL₅₀ on plant matrix

Value

1.4

Note

Published literature RL₅₀ range 0.8-1.7 days,2 field crops, various matrices, n=3

Dissipation rate RL₅₀ on and in plant matrix

Value

3.9

Note

Published literature RL₅₀ range 3.0-4.7 days, 2 field crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

5.5

Moderately fast

Note

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

Value

160

Persistent

Note

pH sensitive: DT₅₀: >1 year at pH 4, 33 hours at pH 9

Water-sediment DT₅₀ (days)

27.6

Fast

Water phase only DT₅₀ (days)

0.5

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

1216

Non-mobile

K_oc

104491

Notes and range

EU 2018 dossier K_d range 810-1793 mL g⁻¹, K_oc range 64286-180290 mL g⁻¹, Soils=5

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-2.01

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

4-fluoro-3-phenoxybenzoic acid

Soil

0.127

Major fraction, Relevant

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

Soil

0.405

Major fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

506

Threshold for concern

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 14.3

Rat (as cyfluthrin)

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

1.5

Rat

High

(ppm diet)

100

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

26.7

Unknown species Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 170

Serinus canaria

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 ppm

Colinus virginianus as cyfluthrin

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

2.6

Anas platyrhynchos NOAEL

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.000068

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000032

Oncorhynchus mykiss 72 day

High

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

0.00029

Daphnia magna

High

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

0.00014

Daphnia magna

High

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

0.0000022

Americamysis bahia

High

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00045

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)

0.00004

Chironomus riparius

High

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

> 0.00084

Lemna gibba

High

Non-target plants

> 60

Cabbage cucumber sunflower barley rye
Vegatitive vigour, ER₅₀
as g ha⁻¹

> 60

-
Seedling emergence, ER₅₀
A5 Cabbage, cucumber, sunflower, barley, rye

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

> 0.002

Scenedemus subspicatus

High

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

0.01

Unknown species

Moderate

Honeybees (Apis spp.)

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

0.012

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)

Bumblebees (Bombus spp.)

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

0.46

Bombus terrestris

High

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

0.12

Bombus terrestris

High

Mason bees (Osmia spp.)

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

0.035

Osmia bicornis

High

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)

0.565

Eisenia foetida as EC10 corr

High

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

> 0.825

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

0.163

Mortality
Aphidius rhopalosiphi

% Effect

100

Mortality [Dose: 1.675 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

0.0025

Mortality
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 0.18 g as/ha

Mesocosm study data

NOEAEC mg l⁻¹

0.00005

Aquatic community

NOEAEC mg l⁻¹

0.00001

NOEC Aquatic community

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)

> 14.3

Rat (as cyfluthrin)

High

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.081

Rat (aerosol)

Other Mammal toxicity endpoints

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

0.01

Rat 4wk SF=100

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

0.01

Rat SF=100

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

0.01

Rat 4wk SF=100

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

0.00024

Rat 13wk SF=100

Dermal penetration studies (%)

0.1-13.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

MRLs

European

EU MRL pesticide database

Notes

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

May cause metabolic or neurological disturbances

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 6.1

CLP classification 2013

Health: H300, H330, H362, H361d, H362, H335
Environment: H400, H410

EC Risk Classification

T+ - Very toxic: R26/28
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S36/37/39, S45, S60, S61

WHO Classification

Ib (Highly hazardous / Highly hazardous)

UN Number

Usually 2588

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

beta-cyfluthrin

French

betacyflutrine

German

beta-Cyfluthrin

Danish

betacyfluthrin

Italian

beta-ciflutrina

Spanish

beta-ciflutrina

Greek

beta-cyfluthrin

Polish

beta-cyflutryna

Swedish

betacyflutrin

Hungarian

beta-ciflutrin

Dutch

Record last updated:	13/01/2021
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