Cyfluthrin (Ref: OMS 2012)

Cyfluthrin (Ref: OMS 2012)	Last updated: 05/01/2021
(Also known as: cyfluthrine; cyfoxylate; BAY FCR 1272)

GENERAL INFORMATION

Description

An insecticide effective against a range of chewing & sucking pests including Lepidoptera, Coleoptera and Hemiptera

Example pests controlled

Corn rootworm; Cutworms; Wireworms; Maggots; Seedcorn beetles; White grubs; Thrips; Cockroaches; Mosquitoes; Silverfish; Corn borer

Example applications

Field corn; Sweetcorn; Popcorn; Silage corn; Citrus; Public health situations

Efficacy & activity

Availability status

Current

Introduction & key dates

1983

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

Germany

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

Chiral, existing as four diastereoisomer pairs (8 enantiomers)

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

No data

International Chemical Identifier key (InChIKey)

QQODLKZGRKWIFG-UHFFFAOYSA-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

920 +/- 25 g kg⁻¹

Known relevant impurities

EU dossier - Only 1% water declared

Substance origin

Synthetic

Mode of action

Non-systemic with contact and stomach action and rapid knock-down effect. Sodium channel modulator.

CAS RN

68359-37-5

EC number

269-855-7

CIPAC number

385

US EPA chemical code

128831

PubChem CID

104926

Molecular mass

434.29

PIN (Preferred Identification Name)

(E)-cyano(4-fluoro-3-phenoxyphenyl)methyl (1E,3E)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

IUPAC name

(RS)-α-cyano-4-fluoro-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

CAS name

cyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Other status information

Chemical subject to PIC regulations

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

Aedes aegypti, Aphis gossypii, Musca domestica, Spodoptera litura, Heliothis virescens, many others

Physical state

Amber coloured viscous part crystalline / part oil paste like substance

Formulations

Property

Value

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

Baythroid
Solfac
Tempo
Aztec

Example products using this active

Makhteshim
Bayer CropScience
Scotts Company

Formulation and application details

Often supplied as an emulsifiable concentrate which is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.0066

Low

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

200000

Toluene

10000

n-Hexane

200000

Dichloromethane

Melting point (°C)

Isomer specific

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

1.00 X 10⁰⁶

Calculated

Log P

High

Bulk density (g ml⁻¹)

1.28

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0003

Low volatility

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

5.30 X 10^-02

Non-volatile

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

No absorption above 290nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

680

Very persistent

DT₉₀ (field)

133

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 48-54 days, DT₉₀ range 53-1664 days, field study DT₅₀ range 26-40 days (Germany)

Dissipation rate RL₅₀ on plant matrix

Value

6.7

Note

Published literature RL₅₀ range 1.7-21.5 days, 4 field crops, various matrices, n=5

Dissipation rate RL₅₀ on and in plant matrix

Value

2.2

Note

Published literature RL₅₀ range 0.8-5.9 days, 10 field & undercover grown crops, various matrices, n=15

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

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

Value

215

Persistent

Note

Stable pH 4 to pH 7, DT₅₀ 1.6 days at pH 9, 20 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

1369

Non-mobile

K_oc

123930

Notes and range

EU dossier K_d range 1116-1793 mL g⁻¹, K_oc range 73484-180290 mL g⁻¹, Soils=4

Freundlich

K_f

1.02

K_foc

¹/_n

1.1

Notes and range

Soil with 68% loam, 24% silt, 8% clay, pH 6.5, OC=2.1%

pH sensitivity

Adsorption decreases with increasing pH and increasing organic carbon

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.66

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

0.100

Major fraction, Relevant

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

Soil

0.100

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2-amino-1-(4-fluoro-3-phenoxyphenyl)-2 oxoethyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Soil (aerobic)

4-fluro-3-phenoxybenamide

Soil (aerobic)

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)

> 16.2

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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)

> 5000 mg kg feed⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00047

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00001

Oncorhynchus mykiss

High

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

0.00016

Daphnia magna

High

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

0.00002

Daphnia magna

High

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

0.000002

Americamysis bahia

High

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

0.00011

Chironomus riparius EC5

High

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)

Non-target plants

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

> 10

Scenedemus subspicatus

Low

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)

0.001

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)

> 0.36

Bombus terrestris

High

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

> 0.11

Bombus terrestris

High

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)

0.008

Megachile rotundata

High

Mode of exposure

Contact

Other pollinators (2)

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

0.003

Nomia melanderi

High

Mode of exposure

Contact

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

> 1000

Eisenia foetida

Low

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

1.63

48 hour
Aphidius rhopalosiphi protonymph

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

0.42

7 day
Typhlodromus pyri protonymph

% Effect

Soil micro-organisms

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

Dose: 0.75 kg as/ha

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)

> 16.2

Rat

High

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

4.05

Rat

Other Mammal toxicity endpoints

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

0.003

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

0.02

Rat SF=100

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

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

0.02

Rat 90 day SF=100

Dermal penetration studies (%)

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

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Highly toxic
Possible liver or kidney toxicant

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 6.1

CLP classification 2013

Health: H300, H331
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

cyfluthrin

French

cyfluthrine

German

Cyfluthrin

Danish

cyfluthrin

Italian

ciflutrin

Spanish

ciflutrin

Greek

cyfluthrin

Polish

cyflutryna

Swedish

cyflutrin

Hungarian

ciflutrin

Dutch

cyfluthrin

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