Lufenuron (Ref: CGA 184699)

Lufenuron (Ref: CGA 184699)	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

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

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

Spain/Hungary

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Yes

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

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)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
lufenuron	-

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

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)

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

Match 50 EC
Libertad
Ferfenuron

Example products using this active

Syngenta
AgroCare

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

Property

Value

Source; quality score; and other information

Interpretation

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

0.046

Low

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

460000

Acetone

330000

Ethyl acetate

100

Hexane

66000

Toluene

Melting point (°C)

169.1

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

242

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.32 X 10⁰⁵

Calculated

Log P

5.12

at 25 °C

High

Bulk density (g ml⁻¹)

1.66

Dissociation constant pKa) at 25 °C

10.2

Very weak acid

Vapour pressure at 20 °C (mPa)

4.00 X 10^-03

Low volatility

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

3.41 X 10^-02

Non-volatile

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

Surface tension (mN m⁻¹)

68.3-72.8

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

16.3

Non-persistent

DT₅₀ (lab at 20 °C)

20.8

Non-persistent

DT₅₀ (field)

256

Persistent

DT₉₀ (lab at 20 °C)

100.3

Persistent

DT₉₀ (field)

937

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

Note

Spring onion leavers, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

10.4

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

Fast

Note

DT₅₀ 111-1781 days in natural light, summer to winter 40 deg N

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

Value

Stable

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

112

Slow

Water phase only DT₅₀ (days)

112

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

1056

Non-mobile

K_foc

41182

¹/_n

0.98

Notes and range

EU dossier K_f range 166-2350 mL g⁻¹, K_foc range 11888-74833 mL g⁻¹, ¹/_n range 0.81-1.06, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.48

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

(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

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

5300

High potential

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

2000

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

966 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)

> 29

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.02

Pimephales promelas

Moderate

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

0.0013

Daphnia magna

High

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

0.0001

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

Chironomus riparius

High

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

0.04

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

Pseudokirchneriella subcapitata Growth

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)

> 200

Low

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

> 197

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)

0.2

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

100

>, 7 day
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

7 day
Coccinella septempunctata

% Effect

Soil micro-organisms

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

Dose: 1.5 kg ha⁻¹ 28 days

Mesocosm study data

NOEAEC mg l⁻¹

0.0001

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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.35

Rat 4 hr (nose only aerosol)

Other Mammal toxicity endpoints

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

0.015

Dog 1year 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)

0.01

Dog 1year SF=100

Dermal penetration studies (%)

2-13

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Negligible risk to bystanders

Occupational

Farm workers should use protective clothing and equipment

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.053

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver and thyroid toxicant

Handling issues

Property

Value and 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)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

lufenuron

French

lufenuron

German

Lufenuron

Danish

lufenuron

Italian

lufenuron

Spanish

lufenuron

Greek

Polish

lufenuron

Swedish

Hungarian

lufenuron

Dutch

Record last updated:	12/01/2021
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