| flupyradifurone (Ref: BYI 02960) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for flupyradifurone
Description: A novel insecticide used to control sucking pests in a variety of cropping situations.
Example pests controlled: Aphids, Hoppers, Whiteflies, Cicadas
Example applications: Vegetables; Fruits; Grapes; Date palm; Coffee; Cocoa
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 2012 discovered
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Netherlands |
| Date inclusion expires | 09/12/2025 |
| 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
Chemical structure:
| Isomerism | - |
| Chemical formula | C12H11ClF2N2O2 |
| Canonical SMILES | C1C(=CC(=O)O1)N(CC2=CN=C(C=C2)Cl)CC(F)F |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | QOIYTRGFOFZNKF-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C11H9ClF2N2O2/c12-9-2-1-7(4-15-9)16(5-10(13)14)8-3-11(17)18-6-8/h1-4,10H,5-6H2 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide | |||
| Substance group | Butenolide | |||
| Minimum active substance purity | >960 g/kg | |||
| Known relevant impurities | EU Dossier: none delcared | |||
| Substance origin | Synthetic | |||
| Mode of action | Systemic, a nicotinic AChR agonist active via ingestion and contact. It is an adult knockdown product that also offers some control of nymph and egg stages. | |||
| CAS RN | 951659-40-8 | |||
| EC number | - | |||
| CIPAC number | - | |||
| US EPA chemical code | 122304 | |||
| PubChem CID | 16752772 | |||
| Molecular mass (g mol-1) | 288.68 | |||
| PIN (Preferred Identification Name) | 4-([(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino)furan-2(5H)-one | |||
| IUPAC name | 4-((6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino)furan-2(5H)-one | |||
| CAS name | 4-(((6-chloro-3-pyridinyl)methyl)(2,2-difluoroethyl)amino)-2(5H)-furanone | |||
| Other status information | - | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | Unknown | |||
| Fungicide Resistance Classification (FRAC) | Not applicable | |||
| Examples of recorded resistance | - | |||
| Physical state | White powder with weak, uncharacteristic odour at 99.4% purity | |||
| 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 | No UK approval for use as a pesticide under EC Regulation 1107/2009 | |||
| Formulation and application details | The main available formulations are those for foliar and drench/drip use and a seed treatment. | |||
ENVIRONMENTAL FATE
for flupyradifurone
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 3200 | A5 | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | 0.05 | E4 - n-Heptane | - | |
| 3700 | E4 - Toluene | - | ||
| 250000 | E4 - Ethyl acetate | - | ||
| 250000 | E4 - Methanol | - | ||
| Melting point (oC) | 69.0 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 270 | A5 | - | |
| Flashpoint (oC) | Not expected to self-ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.58 X 1001 | Calculated | - |
| Log P | 1.2 | A5 - @ 25 DegC | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.43 | A5 | - | |
| Dissociation constant (pKa) at 25oC | - | n/ - | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 9.1 X 10-04 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 8.2 X 10-08 | A5 | Non-volatile | |
GUS leaching potential index  |
3.53 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 6.15 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | pH 7.0: 213nm=9615; 259nm=25800 pH 2.0: 214nm=9389, 259nm=26577 pH 10.0: 213nm=9996; 259nm=25955 |
A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 57.1 | A5 | Moderately persistent |
| DT50 (lab at 20oC) | 57.1 | A5 | Moderately persistent | |
| DT50 (field) | 130 | R4 | Persistent | |
| DT90 (lab at 20oC) | 522.5 | A5 | - | |
| DT90 (field) | - | - | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 38.6-210 days, DT90 range 209-898 days, Soils =16; Manufacturers data DT50 lab studies range 33-371 days; DT50 field ranges 8.3 - 251 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 | 0.35 | E3 | Fast |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | - | - | - |
| Note | - | |||
| Water-sediment DT50 (days) | 230 | E4 | Slow | |
| Water phase only DT50 (days) | 31.4 | E4 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | E4 | Moderately mobile |
| Koc | 98.4 | |||
| Notes and range | Data for European and US soils; Brazilian soils Koc = 333 mL/g | |||
| Freundlich | Kf | 2.26 | A5 | Moderately mobile |
| Kfoc | 98.4 | |||
| 1/n | 0.866 | |||
| Notes and range | EU dossier Kf range 0.597-3.822 mL/g, Kfoc range 85.2-132.2 mL/g, 1/n range 0.845-0.902, Soils=6 | |||
| pH sensitivity | None | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 6-chloronicotinic acid |
Soil | 0.171 | Major fraction; Relevant | |
| difluoroacetic acid |
Soil | 0.339 | Major fraction; Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| 4-[(2,2-difluoroethyl)amino]furan-2(5H)-one | DFEAF | Plants; Livestock; Soil; Water | - | - |
| (6-chloropyridin-3-yl)methanol | CHMP | - | - | - |
| flupyradifuronehydroxy | BYI 02960-hydroxy | - | - | - |
| flupyradifuronesuccinamide | BYI 02960-succinamide | - | - | - |
| flupyradifuroneazabicyclosuccinamide | BYI 02960-azabicyclosuccinamide | - | - | - |
ECOTOXICOLOGY
for flupyradifurone
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | - | - | - |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 300 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | 232 | A5 Colinus virgianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 70.5 | A5 Pimephales promelas | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 4.4 | E4 Pimephales promelas | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 77.6 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 3.2 | E4 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) | > 67.7 | A5 Lemna gibba | Low | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 100 | A5 Pseudokirchneriella subcapitata | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 200 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | 1.2 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 185.6 | A5 Eisenia foetida | Moderate | |
| 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 | 0.5 | < E4 Aphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 17.3 | E4 Typhlodromus pyri | - |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 3.34 mg kg-1 soil, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for flupyradifurone
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) | > 300 | A5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 4.67 | A5 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.064 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.15 | 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) | 0.06 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 0.4-17 | A4 Concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | - | |||
| 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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| General human health issues | Liver and thyroid target organs | |||||||
: 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 | None allocated at this time | |||
| EC Risk Classification |
None allocated at this time | |||
| EC Safety Classification |
- | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | - | - | ||
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
TRANSLATIONS
for flupyradifurone
| Language | Name |
| English | flupyradifurone |
| French | flupyradifurone |
| German | - |
| Danish | - |
| Italian | - |
| Spanish | - |
| Greek | - |
| Slovenian | - |
| Polish | - |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Thursday 31 May 2018
Contact: aeru@herts.ac.uk