| bifenthrin (Ref: FMC 54800) |
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Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
SUMMARY
Bifenthrin is a pyrethroid insecticide used to control a range of pests. It has a low aqueous solubility and is volatile. There is a low risk of groundwater contamination based on its chemical properties and it is not persistent in soil. There are some concerns about bioaccumulation and the pesticide shows a high oral toxicity to mammals as well as being an endocrine distupter and a neurotoxicant. It is toxic to birds, most aquatic organisms, honeybees and earthworms. GENERAL INFORMATION 
for bifenthrin
Description: A pyrethroid acaricide/insecticide for use in a wide range of crops to control sucking and biting foliar pests
Example pests controlled: Fire ants; Blue grass weevil; Armyworms; Cutworms; centipedes; Crickets; earwigs; Millipedes; Sowbugs; Mole crickets; Ticks; Fleas; Grasshoppers
Example applications: Non-cropped situations including lawns, athletic fields, ornamentals, residences and commercial buildings
Efficacy & activity: -
Availability status: Current
Introduction & key dates: circa 1984
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Belgium/Hungary |
| Date inclusion expires | 31/07/2021 |
| 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: Australia, USA
Chemical structure:
| Isomerism | Bifenthrin is chiral molecule and is a mixture of the Z-isomer (~99.7%) and the E-isomer (~0.3%). |
| Chemical formula | C23H22ClF3O2 |
| Canonical SMILES | CC1=C(C=CC=C1COC(=O)C2C(C2(C)C)C=C(C(F)(F)F)Cl)C3=CC=CC=C3 |
| Isomeric SMILES | CC1=C(C=CC=C1COC(=O)[C@@H]2[C@@H](C2(C)C)/C=C(/C(F)(F)F)\Cl)C3=CC=CC=C3 |
| International Chemical Identifier key (InChIKey) | OXCDWLBJSLVWHB-LKRLXIKPSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C23H22ClF3O2/c1-14-16(10-7-11-17(14)15-8-5-4-6-9-15)13-29-21(28)20-18(22(20,2)3)12-19(24)23(25,26)27/h4-12,18,20H,13H2,1-3H3/b19-12- |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide, Acaricide | |
| Substance group | Pyrethroid | |
| Minimum active substance purity | 930 g/kg | |
| Known relevant impurities | EU dossier - Toluene <5 g/kg | |
| Substance origin | Synthetic | |
| Mode of action | Contact and stomach action with some residual effect. Sodium channel modulator. | |
| CAS RN | 82657-04-3 | |
| EC number | - | |
| CIPAC number | 415 | |
| US EPA chemical code | 128825 | |
| PubChem CID | 6442842 | |
| Molecular mass (g mol-1) | 422.88 | |
| PIN (Preferred Identification Name) | rac-(2-methyl[1,1'-biphenyl]-3-yl)methyl (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate | |
| IUPAC name | 2-methyl-3-phenylbenzyl (1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate | |
| CAS name | (2-methyl(1,1'-biphenyl)-3-yl)methyl (1R,3R)-rel-3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | 3 | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | Bemisia argentifolii Frankliniella occidentalis Plutella xylostella Tetranychus turkestani plus others |
|
| Physical state | Off-white waxy 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 | Buffer probably required in UK - see product label | |||
| Formulation and application details | Often supplied as a soluble or emulsifiable concentrate which is mixed with water and applied as a spray. | |||
ENVIRONMENTAL FATE
for bifenthrin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.001 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 735700 | A5 - Acetone | - | |
| 144500 | A5 - n-Heptane | - | ||
| 48000 | A5 - Methanol | - | ||
| 556300 | A5 - Xylene | - | ||
| Melting point (oC) | 79.6 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 280 | A5 | - | |
| Flashpoint (oC) | 151 | L3 - (closed cup) | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 3.98 X 1006 | Calculated | - |
| Log P | 6.6 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.26 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | H3 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 0.0178 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 7.74 X 10-05 | A5 | Non-volatile | |
GUS leaching potential index  |
-2.76 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 5.35 X 10-03 | Calculated | - |
| Note | Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | All pH's: 250nm = 3282.9, sigificant absorption 290-300nm | A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 26 | Q3 | Non-persistent |
| DT50 (lab at 20oC) | 102.2 | A5 | Persistent | |
| DT50 (field) | 86.8 | A5 | Moderately persistent | |
| DT90 (lab at 20oC) | 346.5 | A5 | - | |
| DT90 (field) | 3410.8 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 54.2-173.7 days, DT90 range 223-577 days, field studies DT50 range 5.4-267 days, DT90 range 135.3-965.2 days; Other studies DT50 (1) range 65-125 days, (2) range 2-6 months depending on soil type. | |||
| Dissipation rate RL50 on plant matrix | Value | 6.1 | R4 | - |
| Note | Published literature RL50 range 1.3-27.0 days, 5 field & undercover grown crops, various matrices, n=6 | |||
| Dissipation rate RL50 on and in plant matrix | Value | 4.5 | R4 | - |
| Note | Published literature RL50 range 0.8-14.0 days, 11 field & undercover grown crops, various matrices, n=20 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 12 | B5 | Moderately fast |
| Note | DT50: 255 days in natural sunlight, 12 days in artifical light | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable pH 5 to pH 9 at 25 degC. Hydrolysis occurs at elevated temperatures e.g. DT50 20 mins at pH 4, 90 degC | |||
| Water-sediment DT50 (days) | 161 | A5 | Slow | |
| Water phase only DT50 (days) | 8 | K4 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 3567 | A5 | Non-mobile |
| Koc | 236610 | |||
| Notes and range | EU dossier Kd range 992-5429 mL/g, Koc range 130526-301611 mL/g, Soils=4 | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| (1RS,3RS)-3-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid |
Soil | 0.116 | Major fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| (2-methylbiphenyl-3-yl)methyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2-(hydroxymethyl)-2-methylcyclopropanecarboxylate | OH-methyl bifenthrin | Animal; Hens (eggs); Soil | - | - |
| (4'-hydroxy-2-methylbiphenyl-3-yl)methyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylate | 4'-OH bifenthrin | (a) Sediment; (b) Soil | b=0.08 | - |
| 2-methyl-3-phenylbenzoic acid | BP acid | Plant; Animal; Soil | - | - |
| 2-methyl-3-phenylbenzyl alcohol | BP alcohol | Plant; Soil; Water | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 1703 | E4 | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 54.5 | A5 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | > 5 | B5 Rat | High |
| (ppm diet) | > 100 | - | ||
| Birds - Acute LD50 (mg kg-1) | 1800 | A5 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | 4450 mg kg feed-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.00026 | A5 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.000012 | A5 Salmo gardneri | High | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.00011 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.0000013 | A5 Daphnia magna, LOEC | High | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 0.0000012 | A5 Americamysis bahia | High | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 0.00032 | A5 Chironomus riparius | High | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.822 | A5 Scenedemus subspicatus | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 10 | Q2 Unknown species | Low | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 0.015 | F2 Apis mellifera, Unclear if data is for product or active | High |
| Oral acute 48 hour LD50 (μg bee-1) | 0.1 | A5 | High | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 8.0 | A5 Eisenia foetida, corr | High | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 1.065 | A5 Eisenia foetida, 56 days corr | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | 100 | Mortality Dose: 60g ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | 0.113 | A5 Typhlodromus pyri | - |
| % Effect | 100 | Mortality Dose: 60g ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 0.128 mg kg-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | 0.000015 | A5 Gammarids, copepods & chaoboridae | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for bifenthrin
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) | 54.5 | A5 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 1.01 | A5 Rat, 4 hr | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.015 | A5 Dog, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.03 | 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) | 0.0075 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | 18 | A5 | - | |
| Dangerous Substances Directive 76/464 | List II | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Bystanders should not access orchards or vineyards during spraying | ||
| Occupational | Some risk identified especially during orchard spraying - PPE advised | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | 0.1 | EU Dir 89/778/EC limit; Calc MAC=45.0 μg l-1; A5 | - | |
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 | May cause tremors and staggered gait USEPA - 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 |
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| General |
Not explosive or oxidising IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H300, H317, H331, H351, H372 Environment: H400, H410 |
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| EC Risk Classification |
Carcinogen category 3: R40 T - Toxic: R25, R23 Xn - Harmful: R22, R48 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
- | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | II | - | Warning - Moderately toxic | |
| UN Number | 3349 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| Language | Name |
| English | bifenthrin |
| French | bifenthrine |
| German | Bifenthrin |
| Danish | bifenthrin |
| Italian | bifentrin |
| Spanish | bifentrin |
| Greek | - |
| Slovenian | bifentrin |
| Polish | bifentryna |
| Swedish | - |
| Hungarian | bifenthrin |
| Dutch | - |
Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk