| penflufen (Ref: BYF-14182) |
 |
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GENERAL INFORMATION 
for penflufen
Description: A new fungicidal seed treatment of numerous crops including potatoes
Example pests controlled: Black scurf; Stem & stolon canker; Fusarium rot
Example applications: Potatoes; Cereal grains including wheat, barley; Oilseeds; Alfalfa; Legumes; Rice
Efficacy & activity: -
Availability status: Current
Introduction & key dates: -
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | UK |
| Date inclusion expires | 31/01/2024 |
| 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: USA; Canada
Chemical structure:
| Isomerism | - |
| Chemical formula | C18H24FN3O |
| Canonical SMILES | CC1=NN(C(=C1C(=O)NC2=CC=CC=C2C(C)CC(C)C)F)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | GOFJDXZZHFNFLV-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C18H24FN3O/c1-11(2)10-12(3)14-8-6-7-9-15(14)20-18(23)16-13(4)21-22(5)17(16)19/h6-9,11-12H,10H2,1-5H3,(H,20,23) |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Fungicide | |||
| Substance group | Pyrazolium | |||
| Minimum active substance purity | 980 g/kg | |||
| Known relevant impurities | EU dossier - None declared | |||
| Substance origin | Synthetic | |||
| Mode of action | Succinate DeHydrogenase Inhibitor. | |||
| CAS RN | 494793-67-8 | |||
| EC number | - | |||
| CIPAC number | 826 | |||
| US EPA chemical code | 100249 | |||
| PubChem CID | 11674113 | |||
| Molecular mass (g mol-1) | 317.41 | |||
| PIN (Preferred Identification Name) | rac-5-fluoro-1,3-dimethyl-N-{2-[(2R)-4-methylpentan-2-yl]phenyl}-1H-pyrazole-4-carboxamide | |||
| IUPAC name | 2'-[(RS)-1,3-dimethylbutyl]-5-fluoro-1,3-dimethylpyrazole-4-carboxanilide | |||
| CAS name | N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide | |||
| Other status information | Potential marine pollutant; PAN listed Highly Hazardous Chemical | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | 7 | |||
| Examples of recorded resistance | None identified | |||
| Physical state | Off-white coloured powder | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically | - | |||
| Example products using this active |
|
|||
| UK LERAP status | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | Usually applied as a seed treatment. | |||
ENVIRONMENTAL FATE
for penflufen
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 10.9 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 126000 | A5 - Methanol | - | |
| 1600 | A5 - n-Heptane | - | ||
| 62000 | A5 - Toluene | - | ||
| 139000 | A5 - Acetone | - | ||
| Melting point (oC) | 111 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 320 | A4 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.00 X 1003 | Calculated | - |
| Log P | 3.3 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | - | - | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 4.1 X 10-04 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.05 X 10-05 | A5 | Non-volatile | |
GUS leaching potential index  |
3.55 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 7.10 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | Neutral soln: 209nm=23724, 232nm=10939 shoulder; [Acidic soln: 202nm=25030, 230nm=11784 shoulder; [Basic soln: 204nm=23010, 234nm=9868 shoulder | A5 | - | |
| Surface tension (mN m-1) | 61.6 | A5 | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 192 | A5 | Persistent |
| DT50 (lab at 20oC) | 192 | A5 | Persistent | |
| DT50 (field) | 113 | A5 | Persistent | |
| DT90 (lab at 20oC) | 837 | A5 | - | |
| DT90 (field) | 595 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 115-458 days, DT90 range 382-1521 days; Field studies DT50 range 68-224 days, DT90 range 331->1000 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 | 17.3 | A5 | Slow |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable at pH 4,7 & 9 @ 50 DegC | |||
| Water-sediment DT50 (days) | 21 | A5 | Fast | |
| Water phase only DT50 (days) | 246 | A5 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 4.78 | A5 | Moderately mobile |
| Kfoc | 279.9 | |||
| 1/n | 0.920 | |||
| Notes and range | EU dossier Kf range 2.705-6.10 mL/g, Kfoc range 209.6-409.5 mL/g, 1/n range 0.875-0.974, soils=5 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| penflufen-3-hydroxy-butyl |
Soil | 0.17 | Major fraction, Relevant | |
| penflufen-pyrazolyl-AAP |
Soil | 0.115 | Major fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| - | BYF-14182-3,4-dihydroxy-keto-glucuronide | Animal | - | - |
| - | BYF-14182-3,4-dihydroxy-ketone | Animal | - | - |
| - | BYF-14182-homoglutathione | Plant | - | - |
| - | BYF-14182-pyrazole-4-carboximide | Plant | - | - |
| - | BYF-14182-bis-desmethyl-3-carboxylic acid | Plant | - | - |
| - | BYF-14182-4-hydroxy-butyl-malonyl-glucoside | Plant | - | - |
| - | BYF-14182-2,3,4-trihydroxy | Animal | - | - |
| - | BYF-14182-3,4-dihydroxy-glucuronide | Animal | - | - |
| - | BYF-14182-3,4-dihydroxy | Animal | - | - |
| - | BYF-14182-pentanoic acid | Animal | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 142 | A5 | Threshold for concern |
| CT50 (days) | 0.53 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 2000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 4000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 1697 mg kg-1 BW/day | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.103 | A5 Cyprinus carpio | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.023 | A4 Pimephales promelas, 35 days | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 4.66 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 1.53 | 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) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | > 4.7 | A5 |
Moderate | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 5.1 | A5 Pseudokirchneriella subcapitata | Moderate | |
| 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) | > 108.2 | A5 | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 500 | A5 |
Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 16.5 | A5 |
Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | 250 | > A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 250 | > A5 Aphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Carbon mineralisation: No significant adverse effect | A5 Dose: 3.18 mg kg-1 soil, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for penflufen
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) | > 2000 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 2.02 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.04 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.5 | A5 Rat, 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) | 0.077 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | 0.21-1.45 | A5 Concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Acceptable for intended uses | ||
| Occupational | Acceptable with PPC/PPE | |||
| 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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- |
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- |
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| General human health issues | Possible liver and thyroid toxicant USEPA - some evidence to suggest possible human carcinogen |
|||||||
: 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 | |||
| CLP classification 2013 | Health: H351 Environment: H400, H410 |
|||
| EC Risk Classification |
Carcinogen category 3: R40 N - Dangerous for the environment: R50/53 |
|||
| EC Safety Classification |
- | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | - | - | ||
| UN Number | 3082 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| Language | Name |
| English | penflufen |
| French | - |
| German | - |
| Danish | - |
| Italian | - |
| Spanish | - |
| Greek | - |
| Slovenian | - |
| Polish | - |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Friday 14 September 2018
Contact: aeru@herts.ac.uk