| flufenacet (Ref: FOE 5043) |
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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 
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: 
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 |
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Also used in: Philippines; US, Canada, Chile, Kenya, China, iIsrael
Chemical structure:
| 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:
| 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 |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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  |
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 |
Value | 6.56 X 10-02 | Calculated | - |
| Note | - | |||
| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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 |
|
| FOE sulphonic acid (Ref: AE 0841914) |
Soil | 0.263 | Major fraction, Relevant | |
| FOE oxalate (Ref: AE 0841913) |
Soil | 0.265 | Major fraction, Relevant | |
| FOE alcohol (Ref: AND 1403) |
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 | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (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 |
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| 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 | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| 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 |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Not explosive or oxidising IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H302, H317, H373 Environment: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R22, R43, R48/22 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
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 |
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| 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