Bromadiolone (Ref: LM 637)

Bromadiolone (Ref: LM 637)	Last updated: 12/01/2021
(Also known as: broprodifacoum; bromodiolone)

GENERAL INFORMATION

Description

An anti-coagulant coumarin-derivative rodenticide mainly used for indoor applications

Example pests controlled

Rats; Mice

Example applications

Houses; Commercial buildings; Industrial sites

Efficacy & activity

Availability status

Current

Introduction & key dates

1976, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Italy/Romania

Date EC 1107/2009 inclusion expires

31/05/2021

EU Candidate for substitution (CfS)

Yes - low ADI / ARfD / AOEL

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

A chiral molecule which is a mixture of the two isomeric diastereomers (1RS,3RS) and (1RS,3SR) both of which are toxicologically active

Chemical formula

C₃₀H₂₃BrO₄

Canonical SMILES

C1=CC=C(C=C1)C(CC(C2=CC=C(C=C2)C3=CC=C(C=C3)Br)O)C4=C(C5=CC=CC=C5OC4=O)O

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

OWNRRUFOJXFKCU-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C30H23BrO4/c31-23-16-14-20(15-17-23)19-10-12-22(13-11-19)26(32)18-25(21-6-2-1-3-7-21)28-29(33)24-8-4-5-9-27(24)35-30(28)34/h1-17,25-26,32-33H,18H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Rodenticide

Substance group

Coumarin anticoagulant

Minimum active substance purity

970

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

Second generation anticoagulant which blocks prothrombin formation, inhibits blood coagulation

CAS RN

28772-56-7

EC number

249-205-9

CIPAC number

371

US EPA chemical code

112001

PubChem CID

54680085

Molecular mass

527.40

PIN (Preferred Identification Name)

3-[(1E,3E)-3-(4'-bromo[1,1'-biphenyl]-4-yl)-3-hydroxy-1-phenylpropyl]-4-hydroxy-2H-1-benzopyran-2-one

IUPAC name

3-[(1RS,3RS;1RS,3SR)-3-(4'-bromobiphenyl-4-yl)-3-hydroxy-1-phenylpropyl]-4-hydroxycoumarin

CAS name

3-[3-(4'-bromo[1,1'-biphenyl]-4-yl)-3-hydroxy-1-phenylpropyl]-4-hydroxy-2H-1-benzopyran-2-one

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Odourless white powder

Formulations

Property

Value

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

Maki
Coumarin
Tomcat
Sarakat Bromabait
Contrac
Bromone
Maki
Super-Caid

Example products using this active

Certis
Killgerm
Luxan
LiphaTech

Formulation and application details

Usually supplied in ready-to-use bait formulations such as granules, blocks and pellets

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

18.4

Low

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

10000

Ethyl acetate

12000

Acetone

8200

Ethanol

5600

Methanol

Melting point (°C)

199

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.17 X 10⁰⁴

Calculated

Log P

4.07

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

4.04

Weak acid

Vapour pressure at 20 °C (mPa)

2.13 X 10^-05

Low volatility

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

8.99 X 10^-07

Non-volatile

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

Neutral solution: 206-214nm = 74211, 260-266nm = 29157, 312-314nm = 13895
Acidic solution: 206-214nm = 64736, 250-266nm = 33316, 313-314nm = 12263
Alkaline solution: 206-214nm = 127895, 260-266nm = 28526, 312-314nm = 13895

Surface tension (mN m⁻¹)

71.2

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)

Non-persistent

DT₅₀ (field)

4.6

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 2.8-269 days, DT₉₀ range14-658 days

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

0.1

Fast

Note

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

Value

Moderately persistent

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

7.9

Slightly mobile

K_foc

1636

¹/_n

0.77

Notes and range

EU dossier K_d range 5.3-10.4 mL g⁻¹, K_foc range 1563-1709 mL g⁻¹, ¹/_n range 0.652-0.887, Soils=2

pH sensitivity

Lower adsoption under alkaline conditions than under acidic.

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.52

Calculated

Low leachability

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

Value

3.04 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

3-[(1RS)-3-(4'-bromobiphenyl-4-yl)-3-oxo-1-phenylpropyl]-4-hydroxy-2H-chromen-2-one
Note: Moderately persistent

bromadiolone ketone

Soil

0.40

(1RS,3RS)-5-(4'-bromobiphenyl-4-yl)-1,3-diphenylpentan-1-ol

Soil

0.19

(1RS,3RS,5RS)-1-(4'-bromobiphenyl-4-yl)-3,5-diphenylpentane-1,5-diol

Soil

0.25

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

867

Estimated

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 0.56

Rat

High

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)

138

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 8.0

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

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)

0.017

Scenedemus subspicatus

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)

> 4.74

High

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

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

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)

> 0.56

Rat

High

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

1.30

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.0043

Rat 4 hr

Other Mammal toxicity endpoints

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

Not relevant

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

Not relevant

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

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

0.0012

Rabbit SF=857

Dermal penetration studies (%)

1.6

Dangerous Substances Directive 76/464

Exposure Routes

Public

Small risk identified from possible bait contact

Occupational

Absorbed from the gastrointestinal tract, from intact skin, and the respiratory system - PPE/PPC advised

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.016

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

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

Anticoagulant and may cause haemorrhaging
It is very toxic by inhalation, contact with the skin and by ingestion
Slight eye irritant

Handling issues

Property

Value and interpretation

General

Not oxidising or explosive

CLP classification 2013

Health: H300, H310, H330, H360d, H372
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R21, R22

EC Safety Classification

S13, S21/22, S24, S36/37, S46

WHO Classification

Ia (Extremely hazardous)

UN Number

3027

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

bromadiolone

French

bromadiolone

German

Bromadiolon

Danish

bromadiolon

Italian

bromadiolone

Spanish

bromadiolona

Greek

Polish

bromadiolon

Swedish

bromadiolon

Hungarian

Dutch

bromadiolon

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