Bromoxynil (Ref: ENT 20852)

Bromoxynil (Ref: ENT 20852)	Last updated: 22/08/2024
(Also known as: butil chlorofos; bromotril; bromoxynil phenol)

SUMMARY

A widely used herbicide. It has a high aqueous solubility and is not considered to be volatile. The potential for leaching to groundwater is considered low, and it is not expected to be persistent in soil or water systems. It is highly toxic to mammals, is an endocrine disrupter and may cause negative reproduction or development effects. It is moderately toxic to most aquatic and terrestrial biodiversity. The main exceptions are a low toxicity to algae and honeybees by the contact route (not the oral route).

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: Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Endocrine disrupter; Reproduction/development effects

GENERAL INFORMATION

Description

An HBN herbicide used for post-emergence control of annual broad-leaved weeds. it is also a pesticide transformation product

Example pests controlled

Pigweed; Mayweed; Knotweed; Shepherd's purse; Goosefoot; Morning glory; Dwarf marigold; Stinkweed; Cocklebur; Wild radish

Example applications

Cereals including wheat, barley, oats; Lucerne; Corn; Sorghum; Onions; Flax; Mint; Turf; Non-crop land

Efficacy & activity

Proved as effective by extensive use over a prolonged period and via field experiments

Availability status

Current

Introduction & key dates

1963, first reported.

UK regulatory status

UK COPR regulatory status

Phasing out

Date COPR inclusion expires

Expired

UK LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France/Germany

Date EC 1107/2009 inclusion expires

Expired

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

Australia

Chemical structure

Isomerism

None

Chemical formula

C₇H₃Br₂NO

Canonical SMILES

C1=C(C=C(C(=C1Br)O)Br)C#N

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UPMXNNIRAGDFEH-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
bromoxynil	-

General status

Pesticide type

Herbicide, Metabolite

Metabolite Type

Soil

Substance groups

Hydroxybenzonitrile herbicide; Nitrile herbicide

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, contact action with some systemic activity. Inhibits photosynthesis (photosystem II).

CAS RN

1689-84-5

EC number

216-882-7

CIPAC number

US EPA chemical code

035301

PubChem CID

15531

CLP index number

608-006-00-0

Molecular mass

276.9

PIN (Preferred Identification Name)

3,5-dibromo-4-hydroxybenzonitrile

IUPAC name

3,5-dibromo-4-hydroxybenzonitrile

CAS name

3,5-dibromo-4-hydroxybenzonitrile

Other status information

Marine Pollutant; PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

UK Environment Agency non-statutory standard for the protection of aquatic life: freshwater and saltwater annual average 100 µg l⁻¹; max acceptable conc: 1000 µg l⁻¹

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

Clear to white crystalline solid

Related substances & organisms

bromoxynil-butanoate

bromoxynil-heptanoate

bromoxynil-octanoate

bromoxynil-potassium

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

bromoxynil-butanoate

Soil

0.379

Major fraction

bromoxynil-butanoate

Groundwater

Relevant

bromoxynil-octanoate

Soil

0.446

Major fraction

bromoxynil-octanoate

Groundwater

Relevant

bromoxynil-heptanoate

Groundwater

Relevant

bromoxynil-heptanoate

Soil

0.317

Major fraction

bromoxynil-potassium

Groundwater

Relevant

bromoxynil-potassium

Soil

Formulations

Property

Value

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

Barclay
Nufarm
Dow AgroSciences

Example products using this active

Emblem
Brominex
Chipco Buctril
Brominal Plus

Formulation and application details

Spray application

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

38000

High

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

186000

Acetone

80500

Methanol

46700

n-Octanol

51100

Acetonitrile

Melting point (°C)

190.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

270

Flashpoint (°C)

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

1.86 X 10⁰⁰

Calculated

Log P

0.27

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.63

Dissociation constant pKa) at 25 °C

3.86

Weak acid

Vapour pressure at 20 °C (mPa)

0.12

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

8.7 X 10^-07

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

16.4

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

7.7

24 hr

Volatilisation is not considered critical for air pollution

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

In methanol: 221.2nm = 30343, 286.8nm = 18302, 295.0nm=16215

Surface tension (mN m⁻¹)

73.0

at 20 °C 90%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.04

Non-persistent

DT₅₀ (lab at 20 °C)

1.04

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

5.16

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2017 dossier lab studies DT₅₀ range 0.15-4.42 days, DT₉₀ range 0.60-24.17 days, Soils=17; Other sources: field studies from literature (R3), generally DT₅₀ 7-10 days (Q3)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

2.2

Note

Published literature RL₅₀ range 1.1-3.2 days, 2 field crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.5

Fast

Note

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

Value

Stable

Note

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Moderately fast

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)

Moderately mobile

K_oc (mL g⁻¹)

302

Notes and range

Freundlich

K_f (mL g⁻¹)

2.84

Moderately mobile

K_foc (mL g⁻¹)

127.2

¹/_n

0.98

Notes and range

EU 2017 dossier kf range 0.8-5.9 mL g⁻¹; K_foc range 57-256 mL g⁻¹; ¹/_n range 0.937-1.009, Soils=5

pH sensitivity

Yes - lower mobility at low pH

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.71

Calculated

Low leachability

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

Value

1.80 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

1224

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Substance of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

No data

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3,5-di-bromo-4-hydroxybenzoic acid

Major fraction

0.348

3,5-di-bromo-4-hydroxybenzamide

Major fraction

0.216

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2,6-dibromohydroquinone glucoside

Plant

2-bromo-4-cyanophenyl octanoate

M09

Surface water; Sediment

3,4-dihydroxybenzonitrile

M13

Surface water; Sediment

3,5-dibromo-4-hydroxybenzamide

M01

Plant; Surface water; Sediment

3,5-dibromo-4-hydroxybenzoic acid

M02

Mammal; Plant

3,5-dibromo-4-hydroxyphenyl D-glucopyranoside

3-bromo-4,5-dihydroxybenzonitrile

M03

Surface water; Sediment

3-bromo-4-hydroxybenzonitrile

Surface water; Sediment

4-hydroxybenzonitrile

M06

Surface water; Sediment

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

130

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

16.6

Rat 2 yr

High

(ppm diet)

100

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

> 17.75

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

217

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

1380 mg kg feed⁻¹

Anas platyrhynchos

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

15.9

Anas platyrhynchos NOAEL

Moderate

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

Eisenia foetida

Moderate

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

4.5

Eisenia foetida

Moderate

Soil micro-organisms

Nitrogen mineralisation: Low, transient effect
Carbon mineralisation: Low, transient effect

Dose: 3.73 mg kg⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

150

Apis mellifera

Low

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

10.9

Apis mellifera

Moderate

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

14.5

Apis mellifera as bromoxynil

Bumblebees (Bombus spp.)

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

> 100

Bombus terrestris

Low

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)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

30.0

Aphidius rhopalosiphi as octanate

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

9.47

Typhlodromus pyri as octanate

Beneficial insects (Ground beetles) as Mortality LR₅₀ g ha⁻¹

> 655

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

29.2

Lepomis macrochirus

Moderate

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

2.0

Oncorhynchus mykiss

Moderate

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

3.21

Danio rerio

Moderate

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

12.5

Daphnia magna

Moderate

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

3.1

Daphnia magna

Moderate

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

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

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

1.9

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

> 0.286

Chironomus atrella

Moderate

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

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

0.033

Lemna gibba

Moderate

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

0.12

Navicula pelliculosa

Moderate

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

3.13

Green algae population study

Low

Mesocosm study data

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)

130

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.15

Rat

Other Mammal toxicity endpoints

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

0.03

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

0.013

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

0.013

Rat SF=300

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

0.003

Dermal penetration studies (%)

3.5

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded

Occupational

Low risk from registered uses with PPE/PPC, High risk without PPE/PPC

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL expected to deviate from the EU MRL in mid-2023

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Mostly eliminated in the urine as bromoxynil phenol (free and conjugates)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

US EPA - possible human carcinogen
Possible liver and thyroid toxicant

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Health: H301, H317, H330, H360d
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

bromoxynil

French

bromoxynil

German

Bromoxynil

Danish

bromoxynil

Italian

bromoxinil

Spanish

bromoxinil

Greek

bromoxynil

Polish

bromoksynil

Swedish

Hungarian

bromoxynil

Dutch

bromoxynil

Norwegian

Record last updated:	22/08/2024
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