lufenuron (Ref: CGA 184699) ** Translations

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Further data may be found in the VSDB

GENERAL INFORMATION
for lufenuron

Description: An insect growth regulator used to control biting and sucking insects . Also has some veterinary applications.

Example pests controlled: Lepidoptera and Coleoptera larvae; Fleas; Leaf miners; Fruit flies; Rust mites

Example applications: Cotton; Maize; Sugarbeet; Potatoes; Other vegetables; Grapes; Citrus; Other fruit; Ornamentals

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1989, first reported; 1990, first introduced

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

Status	Approved
Dossier rapporteur/co-rapporteur	Spain/Hungary
Date inclusion expires	31/12/2019
EU Candidate for substitution (CfS)	Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
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

Chemical structure:

Isomerism	Lufenuron consists of a pair of enantiomers. A chiral centre exists at the 2-position of the hexafluoropropoxy side-chain.
Chemical formula	C17H8Cl2F8N2O3
Canonical SMILES	C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=CC(=C(C=C2Cl)OC(C(C(F)(F)F)F)(F)F)Cl)F
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	PWPJGUXAGUPAHP-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C17H8Cl2F8N2O3/c18-6-5-11(32-17(26,27)14(22)16(23,24)25)7(19)4-10(6)28-15(31)29-13(30)12-8(20)2-1-3-9(12)21/h1-5,14H,(H2,28,29,30,31)
Structure diagram/image available?	Yes

General status:

Pesticide type	Insecticide, Acaricide, Veterinary substance
Substance group	Benzoylurea
Minimum active substance purity	-
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Systemic, selective, stomach acting, chitin synthesis inhibitor
CAS RN	103055-07-8
EC number	410-690-9
CIPAC number	704
US EPA chemical code	-
PubChem CID	71777
Molecular mass (g mol-1)	511.16
PIN (Preferred Identification Name)	-
IUPAC name	(RS)-1-[2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6-difluorobenzoyl)urea
CAS name	N-(((2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)amino)carbonyl)-2,6-difluorobenzamide
Other status information	-
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	Drosophila melanogaster
Physical state	White solid
Related substances & organisms	fenoxycarb profenofos

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Syngenta AgroCare
Example products using this active	Match 50 EC Libertad Ferfenuron
UK LERAP status	No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details	Usually supplied as an emulsifiable concentrate that is used as an aqueous spray for crop use or as a suspension for injection when used with livestock.

ENVIRONMENTAL FATE
for lufenuron

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		0.046	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		460000	A5 - Acetone	-
		330000	A5 - Ethyl acetate	-
		100	A5 - Hexane	-
		66000	A5 - Toluene	-
Melting point (oC)		169.1	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		242	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.32 X 1005	Calculated	-
	Log P	5.12	A5 - @ 25 degC	High
Bulk density (g ml-1)/Specific gravity		1.66	L3	-
Dissociation constant (pKa) at 25oC		10.2	A5	-
		Note: Very weak acid
Vapour pressure at 20oC (mPa)		4.00 X 10-03	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		3.41 X 10-02	A5	Non-volatile
GUS leaching potential index		-0.81	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	Medium
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: 210nm = 37293; [Acidic solution: 210nm = 30588; [Basic solution: 295nm = 4871; [No absorption between 295-750nm	A5	-
Surface tension (mN m-1)		68.3-72.8	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	16.3	A5	Non-persistent
	DT50 (lab at 20oC)	20.8	A5	Non-persistent
	DT50 (field)	256	A5	Persistent
	DT90 (lab at 20oC)	100.3	A5	-
	DT90 (field)	937	A5	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier lab studies DT50 range 11.1-75.7 days, DT90 range 45.2-276.1 days; field studies DT50 range 151-434 days, DT90 range 503-1444 days
Dissipation rate RL50 on plant matrix	Value	9.8	R3	-
	Note	Spring onion leavers, n=1
Dissipation rate RL50 on and in plant matrix	Value	10.4	R4	-
	Note	Published literature RL50 range 3.0-53.1 days, 7 field & undercover grown crops, various matrices, n=8
Aqueous photolysis DT50 (days) at pH 7	Value	0.75	A4	Fast
	Note	DT50 111-1781 days in natural light, summer to winter 40 deg N
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 5 to pH 9
Water-sediment DT50 (days)		112	A5	Slow
Water phase only DT50 (days)		112	A5	Stable

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	1056	A5	Non-mobile
	Kfoc	41182
	1/n	0.98
	Notes and range	EU dossier Kf range 166-2350 mL/g, Kfoc range 11888-74833 mL/g, 1/n range 0.81-1.06, Soils=5
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
(2,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-propoxy)-phenyl)-urea (Ref: CGA 238277)		Soil	0.318	Major fraction, Relevancy unknown
2,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-propoxy)-phenylamine (Ref: CGA 224443)		Soil	0.328	Major, Relevancy unknown

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
2,6-difluorobenzamide (Ref: CGA 149772) Note: Mol wt = 157; DT50 = 4.4 days	-	Soil (Aerobic)	0.11	-

ECOTOXICOLOGY
for lufenuron

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	5300	A5	High potential
	CT50 (days)	36		-
Mammals - Acute oral LD50 (mg kg-1)		> 2000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	2	L2 Rat, 2 year	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		2000	A5 Anas platyrhynchos	Moderate
Birds - Short term dietary (LC50/LD50)		966 mg kg bw-1 day-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		> 29	A5 Lepomis macrochirus	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		0.02	A5 Pimephales promelas	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.0013	A5 Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.0001	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)		0.002	A5 Chironomus riparius	High
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		0.04	A5 Chironomus riparius	High
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		8.8	A5 Pseudokirchneriella subcapitata, Growth	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 200	A5	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 197	A5	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 500	A5 Eisenia foetida, corr	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	0.2	A5 Folsomia candida, 28 day NOEC	-
Other arthropod (1)	LR50 g ha-1	100	>, 7 day A5 Typhlodromus pyri	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	21	7 day A4 Coccinella septempunctata	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 1.5 kg ha-1, 28 days	-
Mesocosm study data	NOEAEC mg l-1	0.0001	A5	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for lufenuron

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)		> 2000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 2.35	A5 Rat, 4 hr (nose only, aerosol)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.015	A5 Dog, 1year, SF=100	-
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, 1year, SF=100	-
Dermal penetration studies (%)		2-13	A5 concentration dependent	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Negligible risk to bystanders
	Occupational	Farm workers should use protective clothing and equipment
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		0.053	A5	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
				-
General human health issues		Possible liver and thyroid toxicant

: 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 IMDG Transport Code is usually 9
CLP classification 2013		Health: H317 Environment: H400, H410
EC Risk Classification		Xn - Harmful: R43, R48/22 N - Dangerous for the environment: R50, R53
EC Safety Classification		S2, S24, S37, S60, S61
WHO Classification		NL	-	Not listed
US EPA Classification (formulation)		-	-
UN Number		Usually 3077
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for lufenuron

Language	Name
English	lufenuron
French	lufenuron
German	Lufenuron
Danish	lufenuron
Italian	lufenuron
Spanish	lufenuron
Greek	-
Slovenian	lufenuron
Polish	lufenuron
Swedish	-
Hungarian	lufenuron
Dutch	-

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Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk