Bifenthrin (Ref: FMC 54800)

Bifenthrin (Ref: FMC 54800)	Last updated: 12/01/2021
(Also known as: bifenthrine; biphenthrin; biphentrin; biphenate)

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

Description

A broad spectrum 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

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Belgium/Hungary

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece

ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg

LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia

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⁻¹

Known relevant impurities

EU dossier - Toluene <5 g kg⁻¹

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

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)

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

malathion

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Gala 10 EC
Gyro
Starion Flo
Talstar Flo
Brigade
Talstar 8 SC
Bifenture
Capture

Example products using this active

Belchim
Certis
FMC Chemicals
Lapafarm INC
United Phosphorus

Formulation and application details

Often supplied as a soluble or emulsifiable concentrate which is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.001

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

735700

Acetone

144500

n-Heptane

48000

Methanol

556300

Xylene

Melting point (°C)

79.6

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

280

Flashpoint (°C)

151

(closed cup)

Octanol-water partition coefficient at pH 7, 20 °C

3.98 X 10⁰⁶

Calculated

Log P

6.6

High

Bulk density (g ml⁻¹)

1.26

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0178

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

7.74 X 10^-05

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

All pH's: 250nm = 3282.9, sigificant absorption 290-300nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

102.2

Persistent

DT₅₀ (field)

86.8

Moderately persistent

DT₉₀ (lab at 20 °C)

346.5

Persistent

DT₉₀ (field)

3410.8

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

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

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

Moderately fast

Note

DT₅₀: 255 days in natural sunlight, 12 days in artifical light

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable pH 5 to pH 9 at 25 °C. Hydrolysis occurs at elevated temperatures e.g. DT₅₀ 20 mins at pH 4, 90 °C

Water-sediment DT₅₀ (days)

161

Slow

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

3567

Non-mobile

K_oc

236610

Notes and range

EU dossier K_d range 992-5429 mL g⁻¹, K_oc range 130526-301611 mL g⁻¹, Soils=4

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-2.66

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

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1703

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

54.5

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 5

Rat

High

(ppm diet)

> 100

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

1800

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

4450 mg kg feed⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

6.63

Colinius virginianus NOED

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00026

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000012

Salmo gardneri

High

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.00011

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.0000013

Daphnia magna LOEC

High

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0000012

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

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

Scenedemus subspicatus

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Unknown species

Low

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.016

Apis mellifera

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.1

Apis mellifera

High

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.36

Bombus terrestris

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.34

Bombus terrestris

High

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

0.006

Megachile rotundata

High

Mode of exposure

Contact

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 8.0

Eisenia foetida corr

High

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

1.065

Eisenia foetida 56 days corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

100

Mortality [Dose: 60g ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

0.113

Typhlodromus pyri

% Effect

100

Mortality [Dose: 60g ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 0.128 mg kg⁻¹

Mesocosm study data

NOEAEC mg l⁻¹

0.000015

Gammarids copepods & chaoboridae

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

54.5

Rat

High

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.01

Rat 4 hr

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.015

Dog SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.03

Rat SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.0075

Dog SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Bystanders should not access orchards or vineyards during spraying

Occupational

Some risk identified especially during orchard spraying - PPE advised

European MRLs

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

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May cause tremors and staggered gait
USEPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

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

Carcinogen category 3: R40
T - Toxic: R25, R23
Xn - Harmful: R22, R48
N - Dangerous for the environment: R50, R53

EC Safety Classification

WHO Classification

II (Moderately hazardous)

UN Number

3349

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

bifenthrin

French

bifenthrine

German

Bifenthrin

Danish

bifenthrin

Italian

bifentrin

Spanish

bifentrin

Greek

Polish

bifentryna

Swedish

Hungarian

bifenthrin

Dutch

Record last updated:	12/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242