Bromofenoxim (Ref: C9122)

Bromofenoxim (Ref: C9122)	Last updated: 02/01/2021
(Also known as: bromophenoxim)

GENERAL INFORMATION

Description

An obsolete phenoxy selective herbicide once used for grass and broad-leaved weed control especially in cereal crops

Example pests controlled

Brome grass; Barnyardgrass; Crabgrass; Fat hen; Lambsquarters

Example applications

Cereals; Miaze; Grass seed crops; New turf; Linseed (post-emergence)

Efficacy & activity

Availability status

Obsolete

Introduction & key dates

1969, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

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

Also used in

Chemical structure

Isomerism

Chemical formula

C₁₃H₇Br₂N₃O₆

Canonical SMILES

C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])ONC=C2C=C(C(=O)C(=C2)Br)Br

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

XTFNPKDYCLFGPV-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H7Br2N3O6/c14-9-3-7(4-10(15)13(9)19)6-16-24-12-2-1-8(17(20)21)5-11(12)18(22)23/h1-6,19H/b16-6-

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Dinitrophenyl oxime

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Photosynthesis inhibitor with contact action, generates bromoxynil

CAS RN

13181-17-4

EC number

236-129-6

CIPAC number

269

US EPA chemical code

287200

PubChem CID

5360414

Molecular mass

461.0

PIN (Preferred Identification Name)

2,6-dibromo-4-[(E)-N-(2,4-dinitrophenoxy)methanimidoyl]phenol

IUPAC name

3,5-dibromo-4-hydroxybenzaldehyde 2,4-dinitrophenyloxime

CAS name

3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl)oxime

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Off-white coloured crystals

Formulations

Property

Value

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

Dicoprime
Faneron

Example products using this active

Ciba AG
Novartis

Formulation and application details

Usually supplied as a wettable powder, a suspension concentrate or as a soluble concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

9.0

at 25 °C

Low

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

200.0

Hexane

400

Isopropanol

9900

Acetone

200

n-Octanol

Melting point (°C)

196

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

2.00 X 10⁰³

Calculated

Log P

3.3

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

5.46

Weak acid

Vapour pressure at 20 °C (mPa)

1.16 X 10^-06

at 25 °C

Low volatility

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

1.10 X 10^-09

at 25 °C

Non-volatile

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

2.5

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

2.5

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General literature DT₅₀: 0.7-145 days (R3)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Non-persistent

Note

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

1100

Notes and range

Best available data

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

0.38

Calculated

Low leachability

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

Value

1.01 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

bromoxynil (Ref: ENT 20852)

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Estimated

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 1100

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 5560

Coturnix japonica

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.18

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

1.2

Daphnia magna

Moderate

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

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

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

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

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)

2.3

Unknown species

Moderate

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

Honeybees (Apis 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)

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)

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 pollinators (1)

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

Mode of exposure

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)

1300

Unknown species

Low

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Harmful

[Dose: 5100 g ha⁻¹]
Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Harmless

[Dose: 5100 g ha⁻¹]
Chrysoperla carnea

Soil micro-organisms

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)

> 1100

Rat

Moderate

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

3000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

Harmful if swallowed

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H302
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S25, S60, S61

WHO Classification

O/III (Slightly hazardous / Obsolete substance)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

bromofenoxim

French

bromophenoxyme

German

Bromofenoxim

Danish

bromofenoxim

Italian

bromofenoxim

Spanish

bromofenoxim

Greek

bromofenoxim

Polish

bromofenoksym

Swedish

Hungarian

Dutch

bromofenoxim

Record last updated:	02/01/2021
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