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flufenacet (Ref: FOE 5043)
** fluthiamide ** fluofenacet ** thiafluamide ** Translations

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

SUMMARY

Flufenacet is an EU approved oxyacetamide herbicide. It is moderately soluble in water, is not highly volatile but may, under certain conditions, be persistent in soil and water/sediment systems. It is moderately toxic to humans via the oral route and is considered to be a skin sensitiser. With the exception of honeybees where the toxicity is low, flufenacet is either moderately or highly toxici to most fauna and flora.

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

Description: A broad spectrum soil herbicide, often used in conjunction with other herbicides, used, post-emergence, to control grasses and some broad-leaved weeds

Example pests controlled: Certain annual grasses including black-grass, Broad-leaved weeds including velvet leaf, morning glory and common cocklebur

Example applications: Corn; Soybeans; Winter wheat; Winter barley; Potatoes; Sunflowers; Asparagus; Cotton; Chilli; Tobacco

Efficacy & activity: Efficiacy suuported by data derived from field experiments and extensive global use.

Availability status: Current

Introduction & key dates: 1998, USA; 2004, EU

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Poland/France
Date inclusion expires 31/10/2019
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: 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: Philippines; US, Canada, Chile, Kenya, China, iIsrael

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism -
Chemical formula C14H13F4N3O2S
Canonical SMILES CC(C)N(C1=CC=C(C=C1)F)C(=O)COC2=NN=C(S2)C(F)(F)F
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) IANUJLZYFUDJIH-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C14H13F4N3O2S/c1-8(2)21(10-5-3-9(15)4-6-10)11(22)7-23-13-20-19-12(24-13)14(16,17)18/h3-6,8H,7H2,1-2H3
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 Oxyacetamide
Minimum active substance purity 970 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Selective with meristematic activity. Inhibition of VLCFA (inhibition of cell division).
CAS RN 142459-58-3
EC number -
CIPAC number 588
US EPA chemical code 121903
PubChem CID 86429
Molecular mass (g mol-1) 363.33
PIN (Preferred Identification Name) N-(4-fluorophenyl)-N-(propan-2-yl)-2-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}acetamide
IUPAC name 4'-fluoro-N-isopropyl-2-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yloxy]acetanilide
CAS name N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) K3
Herbicide Resistance Classification (WSSA) 15
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state White to tan coloured, odourless solid
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
  • BASF
  • Standon
Example products using this active
  • Artist
  • Cadu Star
  • Firebird
  • Shooter
  • Regatta
  • Axiom
  • Herold SC
  • Fosbury
UK LERAP status None
Formulation and application details Usually supplied as a suspension concentrate and used as a foliar spray.


ENVIRONMENTAL FATE

for flufenacet

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) 51 A5 Moderate
Solubility - In organic solvents at 20oC (mg l-1) 280000 A5 - Acetone -
200000 A5 - Toluene -
8700 A5 - Hexane -
170000 A5 - Propanol -
Melting point (oC) 76 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 150 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 3.16 X 1003 Calculated -
Log P 3.5 A5 High
Bulk density (g ml-1)/Specific gravity 1.45 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.09 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.3 X 10-03 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 2.02 Calculated Transition state
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 6.56 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 Low
Maximum UV-vis absorption L mol-1 cm-1 pH 2: 201nm=18131, 235nm=7307
pH 7: 235nm=7106
pH 10: 235nm=7161
A5 -
Surface tension (mN m-1) 59.4 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 -
Soil degradation (days) (aerobic) DT50 (typical) 19.7 A5 Non-persistent
DT50 (lab at 20oC) 19.7 A5 Non-persistent
DT50 (field) 39.0 A5 Moderately persistent
DT90 (lab at 20oC) 77.5 A5 -
DT90 (field) 132.4 A5 -
DT50 modelling endpoint 57.6 A5 worse case, not normalised. -
Note EU 2017 dossier lab studies DT50 range 7.04-37.4 days, DT90 range 24.4-191.4 days, Soils=10; field studies DT50 range 14.2-68.1 days, DT90 range 53.4-132.4, Soils=16 days
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 Stable A5 -
Note Not a significant degradation route
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 9
Water-sediment DT50 (days) 81 A4 Moderately fast
Water phase only DT50 (days) 54 A4 Stable

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 - DW3 Moderately mobile
Koc 401
Notes and range -
Freundlich Kf 4.38 A4 Moderately mobile
Kfoc 273.3
1/n 0.92
Notes and range EU 2017 dossier Kf range 1.48-8.96 mL/g, kfoc range 161.6-643.5 mL/g, 1/n range 0.848-0.980, Soils=10
pH sensitivity None

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
FOE sulphonic acid (Ref: AE 0841914) This metabolite may cause environmental pollution, click here for further information Soil   0.263   Major fraction, Relevant
FOE oxalate (Ref: AE 0841913) This metabolite may cause environmental pollution, click here for further information Soil   0.265   Major fraction, Relevant
FOE alcohol (Ref: AND 1403) This metabolite may cause environmental pollution, click here for further information Soil   0.212   Major fraction, Relvant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfinyl)acetamide FOE methylsulfoxide Soil; Water; Plant; Rat - -
N-acetyl-S-{2-[(4-fluorophenyl)(isopropyl)amino]-2-oxoethyl}cysteine FOE acetyl cysteine Animal - -
N-acetyl-S-{2-[(4-fluorophenyl)amino]-2- oxoethyl}cysteine FOE des-i-propyl cysteine Rat - -
N-acetyl-3-({2-[(4- fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfinyl)alanine FOE S-oxo cysteine Rat - -
N-(4-fluorophenyl)-N-isopropylacetamide FOE amine acetate Animal; Plant - -
N-(4-fluorophenyl)-2- (methylsulfinyl)acetamide FOE des-i-propyl methylsulfoxide Rat - -
N-(4-fluorophenyl)-2- (methylsulfonyl)acetamide FOE des-i-propyl methylsulfone Animal - -
fluoro-hydroxy-des-i-propyl methylsulfone - Rat - -
N-acetyl-S-(2-fluoro-5-{[(methylsulfonyl)acetyl]amino}phenyl)cysteine hydroxy-des-i-propyl methylsulfone Rat - -
hydroxy-des-i-propyl methylsulfone-glutaminic acid - Rat - -
2,2'-disulfanediylbis[N-(4-fluorophenyl)-Nisopropylacetamide] FOE disulfide Rat - -
N-(4-hydroxyphenyl)acetamide hydroxy-des-i-propyl amine acetate Rat - -
2-amino-5-fluorophenol 2-A-5-FP Rat - -
gamma-glutamyl-S-{2-[(4- fluorophenyl)(isopropyl)amino]-2- oxoethyl}cysteinylglycine FOE glutathione Rat; Animal - -
S-{2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}cysteine FOE cysteine Rat; Animal; Plant - -
5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl hexopyranosiduronic acid thiadone glucuronide Rat; Animal - -
3-hexopyranosyl-5-(trifluoromethyl)-2,3- dihydro-1,3,4-thiadiazol-2-one ThN glucoside Plant - -
2,4-dioxo-4-{[5-(trifluoromethyl)-1,3,4- thiadiazol-2-yl]oxy}butanoic acid Th oxalyl acetic acid Rat - -
N-(4-fluorophenyl)acetamide DIFAAC: BCS-AA22989 Hen - -
N-(4-fluorophenyl)-N-(1-hydroxypropan-2-yl)- 2-(methylsulfonyl)acetamide HOIFAMSO2 Rat; Hen - -
N-(4-hydroxyphenyl)-N-(1-hydroxypropan-2- yl)-2-(methylsulfinyl)acetamide LMeOH-3 Hen - -
N-(4-fluorophenyl)-2-hydroxy-N-acetamide Des-isopropyl-FOE alcohol Rat - -
4-fluoro-N-isopropylaniline 4-Fluoro-N-(1- methylethyl)benzamine Rat - -
3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfinyl)-2-hydroxypropanoic acid FOE sulfinyl lactic acid Plant - -
N-(carboxyacetyl)-3-[2-oxo-5-(trifluoromethyl)-1,3,4-thiadiazol-3(2H)- Th-malonylalanyl conjugate Soybean - -
[(4-fluorophenyl)amino](oxo)acetic acid FOE des-isopropyl oxalate Plant - -
[(4-fluoro-3-hydroxyphenyl)amino](oxo)acetic acid FOE 3-OH-des-isopropyl oxalate Plant - -
3-({2-[(4-fluorophenyl)(isopropyl)amino]-2-oxoethyl}sulfinyl)-2-(hexopyranosyloxy)propanoic acid FOE sulfinyl lactic acid glucoside Plant - -
3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfinyl)-2- (hexopyranosyloxy)propanoic acid FOE sulfonyl lactic acid Plant - -
3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfinyl)alanine FOE cysteine sulfoxide Fish; Plant - -
3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfanyl)-2-hydroxypropanoic acid FOE sulfanyl lactic acid Plant - -
3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfanyl)-2- (hexopyranosyloxy)propanoic acid FOE sulfanyl lactic acid glucoside Plant - -
N-(carboxyacetyl)-S-{2-[(4- fluorophenyl)(isopropyl)amino]-2- oxoethyl}cysteine FOE malonylcysteine conjugate FAM-MalCys IUPAC: N-(carboxyacetyl)-S-{2-[(4- fluorophenyl)(isopropyl)amino]-2- oxoethyl}cysteine Corn - -
N-(4-fluorophenyl)-N-isopropyl-2- sulfanylacetamide FOE free sulfide Animal; Corn - -
2,2,2-trifluoroethanesulfonic acid FOE 5043- trifluoroethanesulfonic acid Soil - -
trifluoroacetic acid - Rat; Plant; Soil - -
4-fluoro-N-methylethylaniline thiodiacetic acid amide FOE thioglycolate sulfide Soil; Water - -
3-({2-[(4-fluorophenyl)(1-hydroxypropan-2- yl)amino]-2-oxoethyl}sulfinyl)alanine isopropyl hydroxy cysteine Fish - -
({2-[(4-fluorophenyl)(isopropyl)amino]-2-oxoethyl}sulfinyl)acetic acid
(Ref: AE 0841915)
FOE thioglycolate sulfoxide Soil; Plants; Water - -
5-(trifluoromethyl)-1,3,4-thiadiazol-2-ol
(Ref: BCS-AA41715)
FOE-thiadone Rat; Plant; Soil; Water - -
2-chloro-N-(4-fluorophenyl)-N-isopropylacetamide
(Ref: BCS-AA70824)
FOE chloroacetanilide Rat; Plant; Soil - -
N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfonyl)acetamide
(Ref: BCS-CO62475)
FOE methylsulfone Rat; Plant; Soil; Water - -
N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfanyl)acetamide
(Ref: BCS-CP38571)
FOE methylsulfide Water; Animal; Corn - -


ECOTOXICOLOGY

for flufenacet

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) 71.4 A5 Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) 598 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) 1.67 A5 Rat High
(ppm diet) 97.5 -
Birds - Acute LD50 (mg kg-1) 1608 A5 Colinus virginianus Moderate
Birds - Short term dietary (LC50/LD50) > 4970 ppm A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 2.13 A5 Lepomis macrochirus Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.2 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 30.9 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 3.26 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 1.78 F3 Americamysis bahia Moderate
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.002 A5 Lemna gibba High
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.00204 A4 Raphidocelis subcapitata, 72 hour High
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 109.2 A5 Apis melifera Low
Oral acute 48 hour LD50 (μg bee-1) > 100 A5 Apis melifera Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 219 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) > 1.2 A5 Eisenia foetida, corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 29 Mortality
Fecundity
Parasitism
Dose: 0.06 kg ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 100 Mortality and Reproduction
Dose: 0.06 kg ha-1
A5 Typhlodromus pyri, protonymph
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 4 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for flufenacet

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) 598 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 3.74 A5 Rat (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.005 A5 Rat, SF=200 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.017 A5 Dog, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.017 A4 Dog, 90 day, SF=100 -
Dermal penetration studies (%) 0.2-4.7 A5 concentration dependent -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded
Occupational No unacceptable risks to operators or other workers identified
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 Potential liver, spleen 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 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 Health: H302, H317, H373
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R22, R43, R48/22
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S13, S24, S37, S60, S61
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) III - Caution - Slightly toxic
UN Number Usually 3077
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for flufenacet

Language Name
English flufenacet
French flufenacet
German Flufenacet
Danish flufenacet
Italian flufenacet
Spanish flufenacet
Greek flufenacet
Slovenian flufenacet
Polish flufenacet
Swedish flufenacet
Hungarian flufenacet
Dutch flufenacet

Record last updated: Monday 05 November 2018
Contact: aeru@herts.ac.uk