Flufenoxuron (Ref: BAS 3071)

Flufenoxuron (Ref: BAS 3071)	Last updated: 18/12/2020
(Also known as: AC 811678; WL 115110)

SUMMARY

Flufenoxuron is an insectide no longer approved for use in the EU. It has a low aqueous solubility, is non-volatile and is not expected to leach to groundwater. It is moderately persistent in soils but will degrade quickly in aquatic systems in the presence of sunlight. Whilst it has a low mammalian toxicity it does have a high potential to bioaccumulate. It is a know respiratory tract irritant but no other significant human health issues have been identified. It is highly toxic to most aquatic organisms and moderately toxic to birds, honeybees and earthworms.

GENERAL INFORMATION

Description

An insecticide used to control immature stages of phytophagous mites and other insect pests

Example pests controlled

Phytophagous mites (including Aculus, Brevipalpus, Panonychus, Phyllocoptruta, Tetranychus spp.)

Example applications

Fruit including apples, cherry, grape, citrus, strawberry; Vegetables including brassicas, onions, leeks, eggplant; Cotton; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1986, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France

Date EC 1107/2009 inclusion expires

Not applicable

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, Japan, Philippines, South Africa

Chemical structure

Isomerism

None

Chemical formula

C₂₁H₁₁ClF₆N₂O₃

Canonical SMILES

C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=C(C=C(C=C2)OC3=C(C=C(C=C3)C(F)(F)F)Cl)F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

RYLHNOVXKPXDIP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H11ClF6N2O3/c22-12-8-10(21(26,27)28)4-7-17(12)33-11-5-6-16(15(25)9-11)29-20(32)30-19(31)18-13(23)2-1-3-14(18)24/h1-9H,(H2,29,30,31,32)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
flufenoxuron	-

General status

Pesticide type

Insecticide, Acaricide

Substance group

Benzoylurea

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU Dossier - 4-(2-chloro-4-(trifluoromethyl)phenoxy)-2-fluoroaniline hydrochloride <1g/Kg; Toluene <2 g kg⁻¹

Substance origin

Synthetic

Mode of action

Growth regulator with contact and stomach action. Inhibitors of chitin biosynthesis.

CAS RN

101463-69-8

EC number

417-680-3

CIPAC number

470

US EPA chemical code

108203

PubChem CID

91766

Molecular mass

488.77

PIN (Preferred Identification Name)

IUPAC name

1-[4-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-fluorophenyl]-3-(2,6-difluorobenzoyl)urea

CAS name

N-(((4-(2-chloro-4-(trifluoromethyl)phenoxy)-2-fluorophenyl)amino)carbonyl)-2,6-difluorobenzamide

Other status information

Chemical subject to PIC regulations, Banned 2011; PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

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

None identified

Physical state

White crystalline solid

Related substances & organisms

alpha-cypermethrin

propylene glycol

Formulations

Property

Value

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

Tenopa
BAS 307 02I
Casette
Cascade

Example products using this active

BASF
Agro-Care Chemical Industry Group Limited
American Cyanamid

Formulation and application details

Available in a variety of formulations including dispersible powders, emulsifiable concentrates and suspension concentrates.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.0043

Low

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

83000

Acetone

3500

Toluene

6000

Xylene

16000

Dichloromethane

Melting point (°C)

167

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

184

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.29 X 10⁰⁵

Calculated

Log P

5.11

at 25 °C

High

Bulk density (g ml⁻¹)

1.58

Dissociation constant pKa) at 25 °C

10.1

Very weak acid

Vapour pressure at 20 °C (mPa)

6.52 X 10^-09

Low volatility

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

2.64 X 10^-06

Non-volatile

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

Neutral solution: 206nm = 31741, 252nm = 17403, 274nm = 18589
Acidic solution: 220nm = 12073, 258nm = 9424, 297nm = 1064
Basic solution: 224nm = 19830, 237nm = 19571

Surface tension (mN m⁻¹)

49.4

at 20°C

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)

72.5

Moderately persistent

DT₅₀ (field)

42.9

Moderately persistent

DT₉₀ (lab at 20 °C)

363

Persistent

DT₉₀ (field)

2052

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 28-130 days, DT₉₀ range 138-477 days, Field studies DT₅₀ 5.8-91.6 days, DT₉₀ range 84.5-8547 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

21.1

Note

Published literature RL₅₀ range 2.1-64.2 days, 4 field & undercover grown crops, various matrices, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

Continuous irradiation

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

Value

267

Persistent

Note

pH sensitive: DT₅₀ 112 days at pH 5, 104 days at pH 7, 36.7 days at pH 9, 2.7 days at pH 12, all at 25 °C (L3)

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

0.7

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

3078

Non-mobile

K_oc

157643

Notes and range

EU dossier K_d range 1738-4250 mL g⁻¹, K_oc range 88240-289747 mL g⁻¹, Soils=5

Freundlich

K_f

9743

Non-mobile

K_foc

486092

¹/_n

1.07

Notes and range

EU dossier K_f range 3021-22898 mL g⁻¹, kfoc range 167874-738650 mL g⁻¹, ¹/_n range 0.99-1.156, Soils=3

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-2.75

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

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

N-(4-(2-chloro-4-(trifluoromethyl)phenoxy)-2-fluorophenyl) urea (Ref: CL 932338)

Soil

0.156

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

unknown (Ref: Reg. no 4110958; WL 132612)
Note: Minor metabolite

Rat

4-[2-chloro-4-(trifluoromethyl]phenoxy]-2-fluorobenzenamine (Ref: Registration no: 241208, CL 359882)
Note: Mol Wt = 305.6; Log P = 3.32; Kow = 4169; Toxicologically relevant

Rat; Soil; Water

difluorobenzoic acid (Ref: Registration no: 206925; CL 245508)
Note: Mol Wt = 158.1

Rat: Surface water; Groundwater

2,6-difluorobenzamide (Ref: Registration no: 102719; CL 21558)
Note: Mol wt = 157.12; Log P = -0.86; Kow = 0.138

Rat; Surface Water

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

700500

High potential

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 3000

Rat

Low

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)

> 1243 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.0049

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00082

Pimephales promelas

High

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

0.000043

Daphnia magna

High

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

0.00007

Daphnia magna

High

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

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

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.000036

Chironomus riparius

High

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

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

Non-target plants

> 80

Avena sativa Allium cepa Pisum sativum Brassica oleracea
Vegetative vigour, ER₅₀
as g ha⁻¹

> 40

Brassica napus Cucumis sativus Pisum sativum Allium cepa
Seedling emergence, ER₅₀
as g ha⁻¹

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

5.11

Pseudokirchneriella subcapitata Biomass

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)

> 100

Low

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

> 109.1

Low

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)

> 500

Eisenia foetida corr

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

0.055

Folsomia candida 28d corr

Other arthropod (1)

LR₅₀ g ha⁻¹

Mortality
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

386

>, Mortality
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 1.28 kg ha⁻¹ 28 days

Mesocosm study data

NOEAEC mg l⁻¹

0.000025

Aquatic insects and zooplankton

NOEAEC mg l⁻¹

0.000010

Aquatic insects and zooplankton

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)

> 3000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.3

Rat

Other Mammal toxicity endpoints

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

0.01

Dog SF=300 Provisional

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)

0.01

Dog SF=250 Provisional

Dermal penetration studies (%)

0.02-2.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

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

Bioaccumulates
May cause anemia
Possible blood, liver, kidney and spleen toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising however fine dust clouds may present an explosive mix
IMDG Transport Code is usually 9

CLP classification 2013

Health: H362
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R20
N - Dangerous for the environment: R50, R53

EC Safety Classification

S22

WHO Classification

III (Slightly hazardous)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

flufenoxuron

French

flufenoxuron

German

Flufenoxuron

Danish

flufenoxuron

Italian

flufenoxuron

Spanish

flufenoxuron

Greek

Polish

flufenoksuron

Swedish

Hungarian

flufenoxuron

Dutch

Record last updated:	18/12/2020
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