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diflufenican (Ref: AE 088657)
** diflufenicanil ** DFF ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for diflufenican

Description: A herbicide used to control grasses and broad-leaved weeds often used in mixtures

Example pests controlled: Wild radish; Hedge mustard; Charlock; Prickly lettuce; Chickweed; Loosestrife; Stinging nettles

Example applications: Clover-based pastures; Field peas; Lentils; Lupins; Winter cereals

Efficacy & activity: Efficacy demonstrated from extensive use and field trials

Availability status: Current

Introduction & key dates: 1985, first reported

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK/Czech Republic
Date inclusion expires 31/12/2018
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: Click to access a note on the approvals information on this site

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: Click here for further information on the general chemical status information used on this site
Isomerism -
Chemical formula C19H11F5N2O2
Canonical SMILES C1=CC(=CC(=C1)OC2=C(C=CC=N2)C(=O)NC3=C(C=C(C=C3)F)F)C(F)(F)F
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) WYEHFWKAOXOVJD-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C19H11F5N2O2/c20-12-6-7-16(15(21)10-12)26-17(27)14-5-2-8-25-18(14)28-13-4-1-3-11(9-13)19(22,23)24/h1-10H,(H,26,27)
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Substance group Carboxamide
Minimum active substance purity 970 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Selective contact and residual action. Bleaching: inhibition of carotenoid biosynthesis.
CAS RN 83164-33-4
EC number -
CIPAC number 462
US EPA chemical code -
PubChem CID 91735
Molecular mass (g mol-1) 394.29
PIN (Preferred Identification Name) N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide
IUPAC name 2',4'-difluoro-2-(α,α,α-trifluoro-m-tolyloxy)nicotinanilide
CAS name N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]-3-pyridinecarboxamide
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) F1
Herbicide Resistance Classification (WSSA) 12
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance Raphanus raphanistrum
Physical state Colourless crystals
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Bayer CropScience
  • DuPont
  • Headland
  • Makhteshim-Agan
  • Nufarm UK
  • Sipcam
Example products using this active
  • Absolute
  • Ardent
  • Bacara
  • Firebird
  • Graduate
  • Ingot
  • Javelin Gold
  • Hurricane SC
  • Othello
  • Pelican
  • Regatta
  • Herold SC600
  • AG-D1-500
UK LERAP status Buffer probably required in UK - see product label
Formulation and application details Often supplied as a soluble concentrate which is mixed with water and applied as a spray.


ENVIRONMENTAL FATE

for diflufenican

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 0.05 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 4700 A5 - Methanol -
65300 A5 - Ethyl acetate -
72200 A5 - Acetone -
114000 A5 - Dichloromethane -
Melting point (oC) 159.5 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 304.6 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 1.58 X 1004 Calculated -
Log P 4.2 A5 High
Bulk density (g ml-1)/Specific gravity 1.54 L3 -
Dissociation constant (pKa) at 25oC - - -
Note:
Vapour pressure at 20oC (mPa) 4.25 X 10-03 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.18 X 10-02 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.29 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 3.07 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 205.5nm = 35616, 282.5nm = 11155, 292.5nm = 9402 A5 -
Surface tension (mN m-1) 71.46 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability Not readily biodegradable
Soil degradation (days) (aerobic) DT50 (typical) 94.5 A5 Moderately persistent
DT50 (lab at 20oC) 94.5 A5 Moderately persistent
DT50 (field) 64.6 A5 Moderately persistent
DT90 (lab at 20oC) 409.7 A5 -
DT90 (field) 540.8 A5 -
DT50 modelling endpoint 94.5 A5 normalised geometric mean -
Note EU 2018 dossier lab studies DT50 (normalised) range 41.4-318 days, DT90 (normalised) range 138-409.7 days Soils=18; field studies DT50 range 224-621 days; Other field studies DT50 range 64.6-571 days, DT90 range 127-1900 days, Soils=9
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value - - -
Note -
Aqueous photolysis DT50 (days) at pH 7 Value 133 A5 Stable
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 9 over 30 days
Water-sediment DT50 (days) 175 A5 Slow
Water phase only DT50 (days) - - -

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd 134.3 A5 Non-mobile
Koc 5504
Notes and range EU 2018 dossier kd range 50.96-210.93 mL/g, Koc range 3841-6598 mL/g, Soils=8
Freundlich Kf 65.9 A5 Slightly mobile
Kfoc 2215
1/n 0.87
Notes and range EU 2018 dossier Kf range 7.87-267.51 mL/g, Kfoc range 1531.6-7431 mL/g, 1/n range 0.68-1.0, Soils=18
pH sensitivity Yes

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
2-(3-trifluoromethylphenoxy)nicotinamide (Ref: AE-0542291) This metabolite may cause environmental pollution, click here for further information Soil   0.263   Major fraction, Relevant
2-(3-trifluoromethylphenoxy)nicotinic acid (Ref: AE-B107137) This metabolite may cause environmental pollution, click here for further information Soil   0.191   Major fraction, Not relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
2,4-difluoroaniline
(Ref: AE C522392)
- Soil (Anaerobic) - -


ECOTOXICOLOGY

for diflufenican

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 1276 A5 Threshold for concern
CT50 (days) 2.4 -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - L2 Rat, 2 year -
(ppm diet) > 40 -
Birds - Acute LD50 (mg kg-1) > 2150 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) > 0.099 A5 Cyprinus carpio High
Fish - Chronic 21 day NOEC (mg l-1) 0.015 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 0.24 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.052 A5 Daphnia magna Moderate
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) 0.1 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) 2.0 A5 Chironomus riparius Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.056 A5 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.00025 A5 Scenedemus subspicatus High
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.0001 A5 Scenedesmus subspicatus High
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Apis meliifera Low
Oral acute 48 hour LD50 (μg bee-1) > 107.4 A5 Apis meliifera 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 438 A5 Folsomia candida, 28 day NOEC mg kg-1 -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 7.7 Mortality
Dose: 187.5 g ha-1
A5 Typhlodromus pyri, adult
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 2.8 Mortality
Dose: 187.5 g ha-1
A5 Aphidius rhopalosiphi, protonymph
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: Not given
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for diflufenican

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.12 A5 Rat, 4 hr (whole body) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.2 A5 Rat, 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) None allocated A5 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.11 A5 Rat, SF=100 -
Dermal penetration studies (%) 0.15-5.0 A5 concentration dependent -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public Negligible risks for bystanders
Occupational No significant risks identified for operators or other farm workers
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

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 No further information available

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

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Environment: H412
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R52, R53
EC Safety Classification Click here to view information omn the EU safety phrases S60, S61
WHO Classification III - Slightly hazardous
US EPA Classification (formulation) No consensus across products or no products available - -
UN Number Variable with product, usually 3077 or 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for diflufenican

Language Name
English diflufenican
French diflufenican
German Diflufenican
Danish diflufenican
Italian diflufenican
Spanish diflufenican
Greek diflufenican
Slovenian diflufenikan
Polish diflufenikan
Swedish diflufenikan
Hungarian -
Dutch diflufenican

Record last updated: Thursday 01 November 2018
Contact: aeru@herts.ac.uk