Bifenox

Bifenox	Last updated: 17/07/2024
(Also known as: C11066; MC-4379)

SUMMARY

Bifenox is a herbicide for the control of broad-leaved weeds and some grasses. It has a low aqueous solubility, is volatile and would not be expected to leach to groundwater. It would also not be expected to persistent in soil or water systems. It has a low mammalian toxicity and no serious health concerns have been identified. Bifenox is moderately toxic to fish, aquatic invertebrates and earthworms but is highly toxic to algae.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish chronic ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health Moderate alert: Mammals chronic toxicity: Moderate Warning: Significant data are missing

GENERAL INFORMATION

Description

A diphenyl ether herbicide for the control of broad-leaved weeds and some grasses

Example pests controlled

Brome; Barnyard grass; Nutsedge; Cleavers; Fathen; Sprangletop; Charlock; Kochia scoparia; Daucus carota

Example applications

Cereals including wheat, barley, corn; Soybeans; Peanuts; Sugarbeet; Rice; Sorghum; OSR; Sunflowers

Efficacy & activity

Availability status

Current

Introduction & key dates

2000, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2029

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Poland/Belgium

Date EC 1107/2009 inclusion expires

31/03/2027

EU Candidate for substitution (CfS)

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
✓		✓	✓		✓	✓		✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₄H₉Cl₂NO₅

Canonical SMILES

COC(=O)C1=C(C=CC(=C1)OC2=C(C=C(C=C2)Cl)Cl)[N+](=O)[O-]

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

SUSRORUBZHMPCO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H20N2O3/c1-12(2)22-17(20)19-18-15-11-14(9-10-16(15)21-3)13-7-5-4-6-8-13/h4-12,18H,1-3H3,(H,19,20)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
bifenox	-

General status

Pesticide type

Herbicide

Substance groups

Nitrophenol ether herbicide

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - 2,4-dichlorophenol < 3 g kg⁻¹, 2,4-dichloroanisole < 6 g kg⁻¹

Substance origin

Synthetic

Mode of action

Selective, absorbed by foliage, new shoots and roots to inhibit protoporphyrinogen oxidase

CAS RN

42576-02-3

EC number

255-894-7

CIPAC number

413

US EPA chemical code

104301

PubChem CID

39230

CLP index number

No data found

Molecular mass

342.1

PIN (Preferred Identification Name)

methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate

IUPAC name

methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate

CAS name

methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate

Other status information

OSPAR soc

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Pale yellow crystals

Formulations

Property

Value

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

Adama
Makhteshim-Agan
Rhone-Poulenc

Example products using this active

Fox
Sabine
Modown
Alibi
Chipco Ronstar Plus

Formulation and application details

Often supplied as a soluble concentrate or wettable powder which were 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)

0.1

Low

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

261000

Xylene

23000

Methanol

1000000

Dichloromethane

320000

Toluene

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

398.6

Flashpoint (°C)

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

4.37 X 10⁰³

Calculated

Log P

3.64

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

0.65

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

4.74 X 10^-05

Low volatility

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

1.62 X 10^-04

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

1.3

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

1.0

24 hr

Volatilisation is not considered critical for air pollution

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

In methanol: 284.5nm = 8980, 436nm = 174
17.6% methanol in water: 301.5nm = 8633, 437nm = 290

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)

8.3

Non-persistent

DT₅₀ (field)

17.3

Non-persistent

DT₉₀ (lab at 20 °C)

36.6

Moderately persistent

DT₉₀ (field)

57.6

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 4-18 days, DT₉₀ range 13.3-59.8 days; field studies DT₅₀ range 8.3-32.1 days, USA, DT₉₀ range 27.7-106.6 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

2.2

Moderately fast

Note

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

Value

265

Persistent

Note

Stable pH 4 to pH 7, DT₅₀ 4 days at pH 9

Water-sediment DT₅₀ (days)

0.11

Fast

Water phase only DT₅₀ (days)

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

69.2

Non-mobile

K_foc (mL g⁻¹)

6475

¹/_n

0.967

Notes and range

EU dossier kf range 0.93-169 mL g⁻¹, K_foc range 500-23000 mL g⁻¹, ¹/_n range 0.766-1.117, Soils=8

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.23

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

6.83 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

Calculated using the Atkinson method. Assumed 5.0E+05 OH/cm³

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

1500

Threshold for concern

CT₅₀ (days)

1.4

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

bifenox acid

Major fraction

0.787

Adama verified

5-(2,4-dichlorophenoxy)-2-aminobenzoic acid methyl ester

2,4-dichlorophenol

5-(2,4-dichlorophenoxy)-2-anthranilate acid

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

bifenox acid

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

5-(2,4-dichlorophenoxy)-2-aminobenzoic acid methyl ester

aminobifenox

Sediment; Animal (faeces)

2,4-dichlorophenol

Sediment

5-(2,4-dichloro-5-hydroxy-phenoxy)-2-nitrobenzoic acid

5-hydroxybifenox acid

Plant

5-(2,4-dichloro-?-hydroxy-phenoxy)-2-nitrobenzoic acid (Ref: LS-825055)

hydroxybifenox acid

Plant

5-(2,4-dichlorophenoxy)-2-anthranilate acid

aminobifenox acid

Water

bifenox acid

Rat (urine)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 80

Rat 2 yr

High

(ppm diet)

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

44.5

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 677 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

290

Coturnix japonica NOEC

Low

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

> 500

Eisenia foetida corr

Moderate

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

> 2.55

Eisenia foetida corr

Moderate

Soil micro-organisms

Nitrogen mineralisation: Up to -21.9%
Carbon mineralisation: No significant adverse effect

Dose: 3.1 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

> 200

Apis mellifera

Low

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

> 200

Apis mellifera

Low

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

Chronic

Notes

Bumblebees (Bombus 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)

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 bee species (1)

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

Mode of exposure

Other bee species (2)

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

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) as % Mortality at dose 0.786 kg ha⁻¹

12.5

Chrysoperla carnea Larva corr

Beneficial insects (Parasitic wasps) as % Mortality at dose 0.69 kg ha⁻¹

Aphidius rhopalosiphi Adult corr

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

24.0

Typhlodromus pyri Protonymph

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.67

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.009

Oncorhynchus mykiss

High

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

0.66

Daphnia magna

Moderate

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

0.00015

Daphnia magna

High

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

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

0.033

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)

0.015

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.0021

Lemna gibba

High

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.00018

Scenedesmus subspicatus

High

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

0.000175

Desmodesmus subspicatus

High

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.91

Rat 4 hr

Other Mammal toxicity endpoints

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

0.3

Mouse SF=100

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

0.5

Rabbit 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)

0.125

Rabbit SF=400

Dermal penetration studies (%)

1-4

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to bystanders

Occupational

Possible risk to operators - PPE advised
Low risk to other farm workers

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Moderately toxic

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Environment: H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

bifenox

French

bifenox

German

Bifenox

Danish

bifenox

Italian

bifenox

Spanish

bifenox

Greek

Polish

bifenoks

Swedish

bifenox

Hungarian

bifenox

Dutch

Norwegian

Record last updated:	17/07/2024
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