| pyraflufen-ethyl (Ref: ET 751) |
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Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for pyraflufen-ethyl
Description: A herbicide used to control broad-leaved weeds and grasses in crops
Example pests controlled: Black nightshade; Clover; Dandelion; Cleavers; Groundsel; Fat hen; Field bindweed; Field pansy; Knotgrass; Shepherd's purse; Volunteer OSR
Example applications: Potatoes; Vines; Non-cropped areas; Turf
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1993, first reported; 1999, first introduced
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Netherlands/Lithuania |
| Date inclusion expires | 31/03/2031 |
| EU Candidate for substitution (CfS) | No |
| 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: Australia
Chemical structure:
| Isomerism | - |
| Chemical formula | C13H9Cl2F3N2O4 |
| Canonical SMILES | CCOC(=O)COC1=C(C=C(C(=C1)C2=NN(C(=C2Cl)OC(F)F)C)F)Cl |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | APTZNLHMIGJTEW-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C15H13Cl2F3N2O4/c1-3-24-11(23)6-25-10-4-7(9(18)5-8(10)16)13-12(17)14(22(2)21-13)26-15(19)20/h4-5,15H,3,6H2,1-2H3 |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide, Dessicant | |
| Substance group | Phenylpyrazole | |
| Minimum active substance purity | 956 g/kg | |
| Known relevant impurities | EU dossier - None declared | |
| Substance origin | Synthetic | |
| Mode of action | Selective with contact action. Inhibition of protoporphyrinogen oxidase (PPO). | |
| CAS RN | 129630-19-9 | |
| EC number | - | |
| CIPAC number | 605.202 | |
| US EPA chemical code | 030090 | |
| PubChem CID | 182951 | |
| Molecular mass (g mol-1) | 413.18 | |
| PIN (Preferred Identification Name) | - | |
| IUPAC name | ethyl 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxyacetate | |
| CAS name | ethyl [2-chloro-5-[4-chloro-5-(difluoromethoxy)-1-methyl-1H-pyrazol-3-yl]-4-fluorophenoxy]acetate | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | E | |
| Herbicide Resistance Classification (WSSA) | 14 | |
| Insecticide Resistance Classification (IRAC) | Not applicable | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | - | |
| Physical state | Cream powder | |
| 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 | Buffer probably required in UK - see product label | |||
| Formulation and application details | Usually supplied as an emulsifiable concentrate. | |||
ENVIRONMENTAL FATE
for pyraflufen-ethyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.082 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 234 | A5 - n-Heptane | - | |
| 7390 | A5 - Methanol | - | ||
| 175000 | A4 - Acetone | - | ||
| 107000 | A4 - Ethyl acetate | - | ||
| Melting point (oC) | 126.8 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 240 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 3.09 X 1003 | Calculated | - |
| Log P | 3.49 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.57 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 4.30 X 10-06 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 2.20 X 10-05 | A5 | Non-volatile | |
GUS leaching potential index  |
-0.35 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 1.43 X 10-05 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | 203nm = 28700, 243nm = 12800, 291nm = 5900, No further maxima between 291 and 700nm | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 0.32 |
A5 | Non-persistent |
| DT50 (lab at 20oC) | 0.32 | A5 | Non-persistent | |
| DT50 (field) | 1.2 | A5 | Non-persistent | |
| DT90 (lab at 20oC) | 3.6 | A5 | - | |
| DT90 (field) | 4.0 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies: DT50 range 0.22-0.41 days, DT90 range 0.73-10.4 days; Field studies DT50 range 0.4-1.4 days, DT90 range 0.9-13.1 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 | 1.4 | A5 | Moderately fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 13.1 | A5 | Non-persistent |
| Note | pH sensitive: Stable at pH 4, rapid at pH 9 | |||
| Water-sediment DT50 (days) | 0.1 | A5 | Fast | |
| Water phase only DT50 (days) | 0.1 | A5 | Fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | A3 | Slightly mobile |
| Koc | 1949 | |||
| Notes and range | EU dossier Koc estimated value | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenoxyacetic acid |
Soil | 0.940 | Major fraction, Relevant | |
| 2-chloro-5-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)-4-fluorophenol |
Soil | 0.190 | Major fraction, Relevant | |
| 4-chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-5-difluoromethoxy-1-methylpyrazole |
Soil | 0.690 | Major fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| ethyl 2-chloro-5-(4-chloro-5-difluoromethoxylpyrazole-3yl)-4-fluorophenoxyacetate | pyrafluthren-ethyl metabolite E-8 | Rat | - | - |
| 2-chloro-5-(4-chloro-5-difluoromethoxylpyrazole-3yl)-4-fluorophenoxyacetic acid | pyrafluthren-ethyl metabolite E-9 | Rat; Plant | - | - |
| 2-chloro-5-(4-chloro-5-difluoromethoxylpyrazole-3yl)-4-fluorophenol | pyrafluthren-ethyl metabolite E-10 | Rat | - | - |
| 4-chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-5-difluoromethoxylpyrazole | pyrafluthren-ethyl metabolite E-11 | Rat | - | - |
ECOTOXICOLOGY
for pyraflufen-ethyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | - | - | - |
| CT50 (days) | - | - | ||
| 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) | > 2000 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5000 mg kg feed-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 0.100 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 10 | A5 Pimephales promelas | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 0.100 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 100 | A5 Daphnia magna | Low | |
| 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) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | 0.0026 | A5 Lemna gibba | High | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.00023 | A4 Raphidocelis subcapitata, 72 hour | High | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 223 | A5 | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | A5 Eisenia foetida | Low | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 1.6 | <, as L product ha-1 (OS-169: Conc 26.5g l-1) A5 Typhlodromus pyri |
- |
| % Effect | 2.1 | Beneficial capacity Dose: 1.33 l ha-1 A5 Aphidius rhopalosiphi, adult |
- | |
| Other arthropod (2) | LR50 g ha-1 | 1.6 | <, as L product ha-1 (OS-169: Conc 26.5g l-1) A5 Aphidius rhopalosiphi |
- |
| % Effect | 100 | Beneficial capacity Dose: 1.33 l ha-1 A5 Typhlodromus pyri, protonymph |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 0.1 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for pyraflufen-ethyl
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) | > 5000 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 5.03 | A5 Rat, 4 hr (nose only) | - | |
| 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) | 0.2 | A5 Rabbit, 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) | 0.112 | A4 Mouse, 90 day, SF=100 | - | |
| Dermal penetration studies (%) | 4-56.0 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | List II | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | No unacceptable risks to bystanders identified | ||
| 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 | Possible kidney, liver and blood toxicant USEPA - some evidence to suggest possible human carcinogen |
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: 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 |
Corrosive Not explosive or oxidising |
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| CLP classification 2013 | Environment: H400, H410 | |||
| EC Risk Classification |
N - Dangerous for the environment: R50, R53 | |||
| EC Safety Classification |
S60, S61 | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | No consensus across products or no products available | - | - | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
TRANSLATIONS
for pyraflufen-ethyl
| Language | Name |
| English | pyraflufen-ethyl |
| French | pyraflufen-ethyl |
| German | Pyraflufen-ethyl |
| Danish | pyraflufen-ethyl |
| Italian | piraflufen-etil |
| Spanish | piraflufen-etil |
| Greek | pyraflufen-ethyl |
| Slovenian | piraflufen-etil |
| Polish | pyraflufen etylu |
| Swedish | - |
| Hungarian | piraflufen-etil |
| Dutch | pyraflufen-ethyl |
Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk