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bifenthrin (Ref: FMC 54800)
** bifenthrine ** biphenthrin ** biphentrin ** biphenate ** Translations

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 Click here for an explantaion of the general chemical status 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: Click to access a note on the approvals information on this site

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

Also used in: Australia, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
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-
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
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 Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Belchim
  • Certis
  • FMC Chemicals
  • Lapafarm INC
  • United Phosphorus
Example products using this active
  • Gala 10 EC
  • Gyro
  • Starion Flo
  • Talstar Flo
  • Brigade
  • Talstar 8 SC
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 Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
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 Click here for a note on the limitations of the GUS 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 Click here for a note on the limitations of the SCI-GROW index 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 Click here for a note on the limitations of the 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 Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
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 Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
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 Click here for further information on 1107/2009 relevancy
(1RS,3RS)-3-((Z)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid This metabolite may cause environmental pollution, click here for further information 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 - -


ECOTOXICOLOGY

for bifenthrin

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
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 Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the 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

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues May cause tremors and staggered gait
USEPA - 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 Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Health: H300, H317, H331, H351, H372
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Carcinogen category 3: R40
T - Toxic: R25, R23
Xn - Harmful: R22, R48
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification II - Moderately hazardous
US EPA Classification (formulation) II - Warning - Moderately toxic
UN Number 3349
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for bifenthrin

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