Cyflumetofen (Ref: OK-5101)

Cyflumetofen (Ref: OK-5101)	Last updated: 15/01/2023
(Not known by any other names)

SUMMARY

Cyflumetofen is an acracide and insecticide. It has a low aqueous solubility and is non-toxic. It tends not to be persistent in the environment. Whilst its toxicity to honeybees is low it t has a moderate to high toxicity to most other biodiversity. Its oral mammalian toxicity is low.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health Moderate alert: Possible Carcinogen; Possible Reproduction/development effects Warning: Significant data are missing

GENERAL INFORMATION

Description

An acaricide active against phytophagous mites at all development stages suitable for use in IPM systems

Example pests controlled

Citrus red mite; Spruce spider mite; Carmine mite; Glover mite; Pacific spider mite; Two-spotted spider mite

Example applications

Fruit including citrus, grapes, apples, pears, plums, strawberries; Tomatoes; Cucumber; Tree nuts

Efficacy & activity

Availability status

Current

Introduction & key dates

2007, first registered, Japan

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/05/2026

UK LERAP status

Cat B

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands

Date EC 1107/2009 inclusion expires

31/05/2023

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
		✓	✓	✓

Additional information

Also used in

Iran

Chemical structure

Isomerism

Cyflumetofen is a chiral molecule. The technical material is an isomeric mixture of the R- and S-forms.

Chemical formula

C₂₄H₂₄F₃NO₄

Canonical SMILES

CC(C)(C)C1=CC=C(C=C1)C(C#N)(C(=O)C2=CC=CC=C2C(F)(F)F)C(=O)OCCOC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

AWSZRJQNBMEZOI-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C24H24F3NO4/c1-22(2,3)16-9-11-17(12-10-16)23(15-28,21(30)32-14-13-31-4)20(29)18-7-5-6-8-19(18)24(25,26)27/h5-12H,13-14H2,1-4H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Acaricide, Insecticide

Substance groups

Bridged diphenyl insecticide

Minimum active substance purity

>975 g kg⁻¹

Known relevant impurities

Substance origin

Synthetic

Mode of action

Highly selective with good knockdown effect and causes loss of motor coordination leading to paralysis and death. Mitochondrial complex II electron transport inhibitor.

CAS RN

400882-07-7

EC number

642-974-5

CIPAC number

721

US EPA chemical code

138831

PubChem CID

11496052

CLP index number

No data found

Molecular mass

447.45

PIN (Preferred Identification Name)

rac-2-methoxyethyl (2R)-2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate

IUPAC name

2-methoxyethyl (RS)-2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-(α,α,α-trifluoro-o-tolyl)propionate

CAS name

2-methoxyethyl α-cyano-α-[4-(1,1-dimethylethyl)phenyl]-β-oxo-2-(trifluoromethyl)benzenepropanoate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

25A

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

White powder

Formulations

Property

Value

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

Otsuka Chemical Co.

Example products using this active

Danisaraba
Scelta 20SC
OK-5101
Sultan

Formulation and application details

Usually formulated as a suspension concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.0281

Low

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

500000

Acetone

500000

Dichloromethane

5160

n-Hexane

98700

Methanol

Melting point (°C)

77.9

Boiling point (°C)

293

Degradation point (°C)

>293

Flashpoint (°C)

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

2.00 X 10⁰⁴

Calculated

Log P

4.3

at 25 °C

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.21

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.0059

Low volatility

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

9.4 X 10^-02

Non-volatile

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

No maxima above 290nm, significant absorption at pH less than 7

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

8.8

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 1.5-153.4 days; Manufacturers published data gives DT₅₀ 0.4-1.8 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.04

Fast

Note

1.3 hours at pH5

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

Value

0.4

Non-persistent

Note

7.7 days at pH4; 6.0 days at pH5; 10mins at pH9

Water-sediment DT₅₀ (days)

1.32

Fast

Water phase only DT₅₀ (days)

1.39

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

2090

Non-mobile

K_oc

173900

Notes and range

EU dossier K_d range 120-4600 mL g⁻¹; K_oc range 6200-450000 mL g⁻¹, Soils=4

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

-1.17

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

Bio-concentration factor

BCF (l kg⁻¹)

170

Whole fish

Threshold for concern

CT₅₀ (days)

2.2

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

cyflumetofen metabolite AB-1

Major fraction

0.216

2-(trifluoromethyl)benzoic acid

Major fraction

0.630

2-(trifluoromethyl)benzamide

Major fraction

0.230

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹)

alpha,alpha,alpha--trifluoro-o-toluic acid (Ref: B1)

Not relevant

2-(trifluoromethyl)benzoic acid

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

A-12

Rat (faeces); Plant

A-20

Rat (faeces)

AB-6

Plant

2-methoxyethyl (RS) – [4-tert-butyl-2-(alpha, alpha, alpha--trifluoro-o-toluoyl)phenyl] cyanoacetate

AB-7

Plant; Water

isopropyl (RS)-2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-(α,α,α-trifluoro-o-tolyl)proprionate

AB-11

Water

(4-tert-butylphenyl) acetonitrile

A-2

Water

5-tert-butyl-2-(2-cyano-1-(2-(trifluoromethyl)phenyl)-4-methoxy-1-oxobutan-2-yl)benzoic acid

AB-15

Water

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(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)

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

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

> 1000

Eisenia foetida

Low

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

Soil micro-organisms

Nitrogen mineralisation NOEC >= 1.36 mg kg⁻¹ soil
Carbon mineralisation NOEL >= 1.36 mg kg⁻¹ soil

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)

> 102

Apis mellifera

Low

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

> 116

Apis mellifera

Low

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 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

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 1400

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 1400

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.63

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 0.072

Cyprinus carpio

Moderate

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

> 0.063

Daphnia magna

High

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

> 0.065

Daphnia magna

Moderate

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

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

> 0.064

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)

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

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

0.037

Pseudokirchneriella subcapitata

Moderate

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

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)

> 2000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.65

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.17

Rat SF=100

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

None allocated

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

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

0.11

Rat SF=147

Dermal penetration studies (%)

21-28

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk considering intended uses

Occupational

PPE advised

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL expected to deviate from the EU MRL in mid-2023

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapidly excreted in the faeces and urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to autoignite; Not highly flammable

CLP classification 2013

Health: H317, H332
Environment: H400

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

cyflumetofen

French

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	15/01/2023
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