flufenoxuron (Ref: BAS 3071) ** AC 811678 ** WL 115110 ** Translations

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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
for flufenoxuron

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

EC Regulation 1107/2009 (repealing 91/414):

Status	Not approved
Dossier rapporteur/co-rapporteur	France
Date inclusion expires	Not applicable
EU Candidate for substitution (CfS)	Not applicable
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

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
Known relevant impurities	EU Dossier - 4-(2-chloro-4-(trifluoromethyl)phenoxy)-2-fluoroaniline hydrochloride <1g/Kg; Toluene <2 g/kg
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 (g mol-1)	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)	15
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	None recorded
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	BASF Agro-Care Chemical Industry Group Limited American Cyanamid
Example products using this active	Tenopa BAS 307 02I Casette Cascade
UK LERAP status	None
Formulation and application details	Available in a variety of formulations including dispersible powders, emulsifiable concentrates and suspension concentrates.

ENVIRONMENTAL FATE
for flufenoxuron

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		0.0043	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		83000	A5 - Acetone	-
		3500	A5 - Toluene	-
		6000	L3 - Xylene	-
		16000	A5 - Dichloromethane	-
Melting point (oC)		167	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		184	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.29 X 1005	Calculated	-
	Log P	5.11	A5 - @ 25 DegC	High
Bulk density (g ml-1)/Specific gravity		1.58	B5	-
Dissociation constant (pKa) at 25oC		10.1	A5	-
		Note: Very weak acid
Vapour pressure at 20oC (mPa)		6.52 X 10-09	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		2.64 X 10-06	A5	Non-volatile
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		-	Calculated	High
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	A5	-
Surface tension (mN m-1)		49.4	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	42	B5	Moderately persistent
	DT50 (lab at 20oC)	72.5	A5	Moderately persistent
	DT50 (field)	42.9	A5	Moderately persistent
	DT90 (lab at 20oC)	363	A5	-
	DT90 (field)	2052	A3	-
	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	R4	-
	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	6	A5	Moderately fast
	Note	Continuous irradiation
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	267	B5	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 degC (L3)
Water-sediment DT50 (days)		53	A5	Moderately fast
Water phase only DT50 (days)		0.7	A5	Fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	3078	A5	Non-mobile
	Koc	157643
	Notes and range	EU dossier Kd range 1738-4250 mL/g, Koc range 88240-289747 mL/g, Soils=5
Freundlich	Kf	9743	A5	Non-mobile
	Kfoc	486092
	1/n	1.07
	Notes and range	EU dossier Kf range 3021-22898 mL/g, kfoc range 167874-738650 mL/g, 1/n range 0.99-1.156, Soils=3
pH sensitivity		No

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	-	-
2,6-difluorobenzamide (Ref: Registration no: 102719; CL 21558) Note: Mol wt = 157.12; Log P = -0.86; Kow = 0.138	-	Rat; Surface Water	-	-
difluorobenzoic acid (Ref: Registration no: 206925; CL 245508) Note: Mol Wt = 158.1	-	Rat: Surface water; Groundwater	-	-
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	-	-

ECOTOXICOLOGY
for flufenoxuron

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	700500	A5	High potential
	CT50 (days)	21		-
Mammals - Acute oral LD50 (mg kg-1)		> 3000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	5	B5 Rat	High
	(ppm diet)	50		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		> 1243 mg kg bw-1 day-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		> 0.0049	A5 Oncorhynchus mykiss	High
Fish - Chronic 21 day NOEC (mg l-1)		0.00082	A5 Pimephales promelas	High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.000043	A5 Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.00007	A5 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	A5 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	A5 Avena sativa, Allium cepa, Pisum sativum, Brassica oleracea Vegetative vigour, ER50 as g/ha	-
		> 40	A5 Brassica napus, Cucumis sativus, Pisum sativum, Allium cepa Seedling emergence, ER50 as g/ha	-
Algae - Acute 72 hour EC50, growth (mg l-1)		5.11	A5 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	A5	Low
	Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	> 109.1	A5	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	A5 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	A5 Folsomia candida, 28d corr	-
Other arthropod (1)	LR50 g ha-1	73	Mortality A5 Typhlodromus pyri	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	386	>, Mortality A5 Aphidius rhopalosiphi	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 1.28 kg ha-1, 28 days	-
Mesocosm study data	NOEAEC mg l-1	0.000025	A5 Aquatic insects and zooplankton	-
	NOEAEC mg l-1	0.000010	A5 Aquatic insects and zooplankton	-

HUMAN HEALTH AND PROTECTION
for flufenoxuron

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		> 3000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 3.3	A5 Rat	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.01	A5 Dog, SF=300 Provisional	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.01	A5 Dog, SF=250 Provisional	-
Dermal penetration studies (%)		0.02-2.0	A5 concentration dependent	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Routes	Public	Acceptable for proposed uses
	Occupational	Acceptable for proposed uses
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Genotoxic	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	A3; B3; C3; D0; E3				-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
		-		-
General human health issues		Bioaccumulates May cause anemia Possible blood, liver, kidney and spleen toxicant
Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative			Key: Other : Yes, known to cause a problem : No, known not to cause a problem : Possibly, status not identified - : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	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
for flufenoxuron

Language	Name
English	flufenoxuron
French	flufenoxuron
German	Flufenoxuron
Danish	flufenoxuron
Italian	flufenoxuron
Spanish	flufenoxuron
Greek	-
Slovenian	flufenoksuron
Polish	flufenoksuron
Swedish	-
Hungarian	flufenoxuron
Dutch	-

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Record last updated: Tuesday 03 March 2020
Contact: aeru@herts.ac.uk