Bromuconazole (Ref: LS 860263)

Bromuconazole (Ref: LS 860263)	Last updated: 02/01/2021
(Also known as: bromoconazole; LS 850646; LS 850647)

GENERAL INFORMATION

Description

A foliar applied conazole fungicide for a range of crops including cereals

Example pests controlled

Rusts; Powdery mildew; Septoria tritici; Leaf spot; Eyespot

Example applications

Cereals including barley, wheat; Fruit; Vegetables; Grapevines; Turf; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1990, first reported; 1992, first marketed France

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2024

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Belgium/Czech Republic

Date EC 1107/2009 inclusion expires

31/01/2024

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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

Chemical structure

Isomerism

A chiral molecule - isomeric mixture of the cis- and trans-form

Chemical formula

C₁₃H₁₂BrCl₂N₃O

Canonical SMILES

C1C(COC1(CN2C=NC=N2)C3=C(C=C(C=C3)Cl)Cl)Br

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

HJJVPARKXDDIQD-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H12BrCl2N3O/c14-9-4-13(20-5-9,6-19-8-17-7-18-19)11-2-1-10(15)3-12(11)16/h1-3,7-9H,4-6H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Triazole

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic. Sterol biosynthesis inhibitor.

CAS RN

116255-48-2

EC number

408-060-3

CIPAC number

680

US EPA chemical code

120503

PubChem CID

3444

Molecular mass

377.06

PIN (Preferred Identification Name)

1-{[(2?,4?)-4-bromo-2-(2,4-dichlorophenyl)oxolan-2-yl]methyl}-1H-1,2,4-triazole

IUPAC name

1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetrahydrofurfuryl]-1H-1,2,4-triazole

CAS name

1-[[4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl]methyl]-1H-1,2,4-triazole

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)

Examples of recorded resistance

Physical state

White to beige powder

Formulations

Property

Value

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

Grannit 200SC
Jazz

Example products using this active

Bayer CropScience
Interfarm

Formulation and application details

Often available as suspension concentrate that is diluted with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

48.3

Low

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

1790

n-Hexane

187000

Toluene

269.2

Acetone

50000

n-Octanol

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

194

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.74 X 10⁰³

Calculated

Log P

3.24

High

Bulk density (g ml⁻¹)

1.72

Dissociation constant pKa) at 25 °C

2.75

Strong acid, pKa (2) -4.02 Very strong acid

Vapour pressure at 20 °C (mPa)

0.004

at 25 °C

Low volatility

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

1.31 X 10^-05

Non-volatile

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

Neutral solution: 202.5nm = 43936, 220nm = 10762
Acidic solution: 202.5nm = 38527, 220nm = 11157
Basic solution: 221.5nm = 9915

Surface tension (mN m⁻¹)

59.8

at 21°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

190

Persistent

DT₅₀ (lab at 20 °C)

679

Very persistent

DT₅₀ (field)

123

Persistent

DT₉₀ (lab at 20 °C)

2253

Very persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 329-1028 days, DT₉₀ range 1091-3414 days; Various other studies lab range 119-1279 days, field studies DT₅₀ range 5-214 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

Stable

Note

No photolytic degradation in pH range 5 to 9

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

Value

Moderately persistent

Note

Not sensitive to pH

Water-sediment DT₅₀ (days)

275

Slow

Water phase only DT₅₀ (days)

1.7

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

872

Notes and range

EU dossier K_oc range isomer LS850646 range 474-1086, LS850647 range 627-1539 mL g⁻¹, Soils=4

Freundlich

K_f

12.51

Slightly mobile

K_foc

860

¹/_n

0.82

Notes and range

UK dossier K_f range 4.75-32.0 mL g⁻¹, K_foc range 575-1333 mL g⁻¹, ¹/_n - no data, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.23

Calculated

Transition state

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

Value

1.13 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

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

Ref: LS850920

hydroxylated metabolite

Plant

Ref: RPA 406117

hydroxylated metabolite

Plant

2-(2,4-dichlorophenyl-2-(1,2,4-triazol-1-yl methyl)) tetrahydrofuran (Ref: LS871387)

Soil (Anaerobic, dark)

1-[2-(2,4-dichlorophenyl)-2,5-dihydrofuran-2-ylmethyl]-1H-1,2,4-triazole (Ref: LS860364)

Rat; Plant; Soil; Fish

Ref: LS860550

3-hydroxy metabolite

Plant

Ref: LS860551

3-hydroxy metabolite

Plant

Ref: LS870353

2-ketone metabolite

Plant

Ref: RPA 401527

5-H-2-ketone metabolite

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

131

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

328

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.99

Rat

High

(ppm diet)

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

> 141

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2150

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Colinus virginianus

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

26.5

Coturnix japonica

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.7

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.21

Oncorhynchus mykiss

Moderate

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

> 8.9

Daphnia magna

Moderate

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

0.02

Daphnia magna

Moderate

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)

0.250

Chironomus riparius

Moderate

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

3.125

Chironomus riparius

Moderate

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

0.12

Lemna gibba

Moderate

Non-target plants

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

> 3.3

Pseudokirchneriella subcapitata

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)

> 500

Apis mellifera

Low

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

> 100

Apis mellifera

Low

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)

> 500

Eisenia foetida corr

Moderate

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

18.6

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

-19.2

Beneficial capacity [Dose: 62.5 mL/ha]
Aphidius rhopalosiphi adults

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

-35.3

Beneficial capacity [Dose: 62.5 mL/ha]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 0.667 mg kg⁻¹ 28days

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)

328

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.0

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.01

Rat SF=100

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

0.1

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)

0.025

Dog SF=100

Dermal penetration studies (%)

5.0-45.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable risks for proposed uses

Occupational

Acceptable risks for proposed uses with PPE

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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

Moderately toxic
Possible liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H302, H361
Environment: H400, H410

EC Risk Classification

Reproduction risk category 3: R63
Xn - Harmful: R22

EC Safety Classification

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

bromuconazole

French

bromuconazole

German

Bromuconazol

Danish

bromuconazol

Italian

bromuconazolo

Spanish

bromuconazol

Greek

Polish

bromukonazol

Swedish

Hungarian

bromukunazol

Dutch

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