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lufenuron (Ref: CGA 184699)
** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
Further data may be found in the VSDB

GENERAL INFORMATION
for lufenuron

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

Introduction: 1989, first reported; 1990, first introduced

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Portugal
Date inclusion expires 31/12/2019

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia

General status:
Pesticide type Insecticide, Acaricide, Veterinary treatment
Substance group Benzoylurea
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 -
Chiral molecule Chiral or specific isomer of a chiral molecule
Chemical formula C17H8Cl2F8N2O3
SMILES Clc1cc(c(Cl)cc1OC(F)(F)C(F)C(F)(F)F)NC(=O)NC(=O)c2c(F)cccc2F
International Chemical Identifier (InChI) InChI=1/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
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 -
Herbicide Resistance Classification (HRAC) Not applicable
Insecticide Resistance Classification (IRAC) 15
Fungicide Resistance Classification (FRAC) Not applicable
Physical state White solid
Related substances & organisms

Formulations:
Property Value
Example manufacturers of products using this active
  • Syngenta
  • AgroCare
Example products using this active
  • Match 50 EC
  • Libertad
  • Ferfenuron
UK LERAP status No UK approval for use or outside scope
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 25oC (mPa) 4.00 X 10-03 A5 Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) 3.41 X 10-02 A5 Non-volatile
Henry's law constant at 20oC (dimensionless) 1.83 X 10-05 Calculated Moderately volatile
GUS leaching potential index -0.75 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 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
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 -
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
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 Very persistent
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 91/414 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 5300 A5 High potential
CT50 (days) 36 -
Bioaccumulation potential - Calculated High
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Moderate
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 -
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 -
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) - - -
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 - Acute 48 hour LD50 (μg bee-1) > 197 A5 Oral Low
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
Moderately harmful at 1 kg ha-1
Harmless at 0.1 kg ha-1
Harmless at 0.01 kg ha-1
% Effect - - -
Other arthropod (2) LR50 g ha-1 21 7 day
A4 Coccinella septempunctata
Harmful at 1 kg ha-1
Moderately harmful at 0.1 kg ha-1
Harmless at 0.01 kg ha-1
% 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
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Moderate
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) 0.0155 A5 Dog, 1year, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) None allocated A5 -
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 dependant -
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
Examples of European MRLs (mg kg-1) Value Grapes: 1.0; Tomatoes: 0.3
Note A5 EU dossier proposals
For the EU pesticides database click here
Drinking Water MAC (μg l-1) 0.053 A5 -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

General human health issues Skin sensitiser
Possible liver and thyroid toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 -
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 -

Record last updated: Monday 09 September 2013
Contact: aeru@herts.ac.uk