Fuberidazole

Fuberidazole	Last updated: 20/11/2020
(Also known as: furidazol; furidazole; fuberidazole (MBC))

GENERAL INFORMATION

Description

A fungicide used mainly as a seed treatment to control a variety of soil and seed borne diseases in cereals

Example pests controlled

Fusarium spp.; Snow mould; Stinking smut

Example applications

Cereals

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1970

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

UK/Finland

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

C₁₁H₈N₂O

Canonical SMILES

C1=CC=C2C(=C1)NC(=N2)C3=CC=CO3

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UYJUZNLFJAWNEZ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H8N2O/c1-2-5-9-8(4-1)12-11(13-9)10-6-3-7-14-10/h1-7H,(H,12,13)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide, Seed treatment

Substance group

Benzimidazole

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with specific action against Fusarium spp. Inhibition of mitosis and cell division (Beta-tubulin assembly in mitosis).

CAS RN

3878-19-1

EC number

223-404-0

CIPAC number

525

US EPA chemical code

PubChem CID

19756

Molecular mass

184.19

PIN (Preferred Identification Name)

IUPAC name

2-(2'-furyl)benzimidazole

CAS name

2-(2-furanyl)-1H-benzimidazole

Other status information

PAN listed Highly Hazardous Chemical

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

Light brown to colourless crystalline powder

Related substances & organisms

imidacloprid

triadimenol

bitertanol

Formulations

Property

Value

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

Tripod Plus
Baytan FS
Voronit

Example products using this active

Makhteshim-Agan
Bayer

Formulation and application details

Usually supplied as a flowable concentrate for use as a seed dressing

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Moderate

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

350

Toluene

14000

Acetone

7900

Ethyl acetate

6600

Dichloromethane

Melting point (°C)

Decomposes on melting

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

292

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

5.13 X 10⁰²

Calculated

Log P

2.71

Moderate

Bulk density (g ml⁻¹)

1.246

Dissociation constant pKa) at 25 °C

Weak base

Vapour pressure at 20 °C (mPa)

9.00 X 10^-04

Low volatility

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

2.00 X 10^-06

Non-volatile

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

298.7nm = 26651, 306.3nm = 33982, 321.5nm = 26243

Surface tension (mN m⁻¹)

72.35

at 20°C

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)

24.6

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

88.7

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 6.3-56.5 days (normalised), DT₉₀ range 20.8-187.7 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

0.15

Fast

Note

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

Value

Stable

Note

Stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

15.1

Fast

Water phase only DT₅₀ (days)

0.59

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

9.84

Slightly mobile

K_foc

605

¹/_n

0.82

Notes and range

EU dossier K_f range 6.24-16.89 mL g⁻¹, K_foc range 420-698 mL g⁻¹, ¹/_n range 0.750-0.866, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.95

Calculated

Low leachability

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

Value

5.12 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

1H-benzimidazole-2-carboxylic acid

Soil

0.147

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

(2E)-4-(1H-benzimidazol-2-yl)-4-oxobut-2-enoic acid

trans-oxobutenoic acid; fuberidazole metabolite M17

Water (Photolysis)

1H-benzimidazole-2-carboxylic acid

fuberidazole metabolite M01

Soil

4-(1H-benzimidazol-2-yl)-4-hydroxybutanoic acid

fuberidazole metabolite M09

Plant

hydroxyfuberidazole glucoside

Rate (Bile)

1-(1H-benzimidazole-2-yl)ethanone
Note: Possible groundwater contaiminant

fuberidazole metabolite M11

Soil

4-(1H-benzimidazol-2-yl)-4-oxobutanal

oxobutanal benzimidazole; fuberidazole metabolite M15

Soil (Photolysis)

(2Z)-4-(1H-benzimidazol-2-yl)-4-oxobut-2-enoic acid

cis-oxobutenoic acid; fuberidazole metabolite M16

Water (Photolysis)

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)

> 300

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 20

Rat 2 year

High

(ppm diet)

> 80

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

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

> 750

Coturnix japonica

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 930 mg kg bw⁻¹ day⁻¹

Coturnix japonica

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

76.9

Colinius virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.91

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

4.7

Daphnia magna

Moderate

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

0.12

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)

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)

1.4

Pseudokirchneriella subcapitata

Moderate

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

0.5

Unknown species

Moderate

Honeybees (Apis spp.)

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

> 200

Low

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

> 187.2

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)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

260.6

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Mortality [Dose: 26 g ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

8.9

Mortality [Dose: 26 g ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 0.07 g kg⁻¹ soil

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)

> 300

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.458

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.0072

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

0.08

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

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

0.0072

Dermal penetration studies (%)

1.0-6.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk of exposure considering patterns of use

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

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 Code is usually 6.1

CLP classification 2013

Health: H302, H317, H351, H373
Environment: H400, H410

EC Risk Classification

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

EC Safety Classification

S2, S22, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 2588

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fuberidazole

French

fuberidazole

German

Fuberidazol

Danish

fuberidazole

Italian

fuberidazolo

Spanish

fuberidazol

Greek

fuberidazole

Polish

fuberidazol

Swedish

fuberidazol

Hungarian

fuberidazol

Dutch

fuberidazool

Record last updated:	20/11/2020
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