Bitertanol (Ref: KWG 0599)

Bitertanol (Ref: KWG 0599)	Last updated: 23/08/2024
(Also known as: biloxazol; baycor)

SUMMARY

Bitertanol is a fungicide that has a low solubility, semi-volatile and has a low risk of leaching to groundwater based on its chemical properties. It is non-persistent in soil and slightly mobile but very persistent in water. There is a moderate risk of bioaccumulation. It is non-toxic to humans but may cause adverse reproduction or developmental effects. It is moderately toxic to most animal and insects but is non-toxic to honeybees.

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: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity High alert: Birds chronic ecotoxicity: High; Fish chronic ecotoxicity: High	Human health High alert: Endocrine disrupter; Reproduction/development effects

GENERAL INFORMATION

Description

A conazole fungicide used to control a range of diseases including scab, powder mildew, rusts and blackspot

Example pests controlled

Scab; Leafspot; Rusts; Mildews; Black spot; Carnation rust;

Example applications

Fruit including bananas; Cereals; Peanuts; Ornamentals and flowers; Beans; Soybeans

Efficacy & activity

Availability status

Current

Introduction & key dates

1980, introduced

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

Sweden/Czech Republic

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, Brazil, Chile, Argentina, Algeria, Costa Rica, Columbia, Ecuador, Indonesia, Mexico, Malaysia, Syria

Chemical structure

Isomerism

A chiral molecule that exists in two diastereomeric forms

Chemical formula

C₂₀H₂₃N₃O₂

Canonical SMILES

CC(C)(C)C(C(N1C=NC=N1)OC2=CC=C(C=C2)C3=CC=CC=C3)O

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

VGPIBGGRCVEHQZ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C20H23N3O2/c1-20(2,3)18(24)19(23-14-21-13-22-23)25-17-11-9-16(10-12-17)15-7-5-4-6-8-15/h4-14,18-19,24H,1-3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Triazole fungicide

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic, protective and curative, inhibiting ergosterol biosynthesis.

CAS RN

55179-31-2

EC number

259-513-5

CIPAC number

386

US EPA chemical code

117801

PubChem CID

91656

CLP index number

No data found

Molecular mass

337.42

PIN (Preferred Identification Name)

reaction mixture of 80% rac-(1R,2S)-1-([1,1'-biphenyl]-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol and 20% rac-(1R,2R)-1-([1,1'-biphenyl]-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

IUPAC name

(1RS,2RS;1RS,2SR)-1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

CAS name

β-([1,1'-biphenyl]-4-yloxy)-a-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

White to grey coloured powder

Formulations

Property

Value

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

Bayer CropScience
King Tech Corp
Mobay

Example products using this active

Sibutol FS398
Sibutol SC500
Bacseal
Baycor
Baycoral
Baymat
Zaron

Formulation and application details

Formulations include suspension concentrates foliar sprays and flowable suspensions for seed treatments

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

3.8

Low

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

250000

Dichloromethane

200000

Acetone

18000

Xylene

53000

n-Octanol

Melting point (°C)

118

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

300

Flashpoint (°C)

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

1.26 X 10⁰⁴

Calculated

Log P

4.1

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.16

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.36 X 10^-06

Low volatility

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

2.6 X 10^-07

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

24 hr

Volatilisation is not considered critical for air pollution

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

Maxima at 255nm, no absorbance above 290nm

Surface tension (mN m⁻¹)

64.0

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)

8.5

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 4-20.4 days, DT₉₀ range 14-42 days; Other studies: lab DT₅₀ range 17-179 days, field DT₅₀ range 19-27 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

9.7

Note

Published literature RL₅₀ range 2.5-16.9 days, 2 field and undercover grown crops, various matrices, n=2

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.4

Note

Published literature RL₅₀ range 2.9-7.8 days, 2 field crops, various matrices, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

DT₅₀: 18 days sterile water, 11 days natural water

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

Value

Stable

Note

Stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

39.2

Moderately fast

Water phase only DT₅₀ (days)

Slow

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

31.8

Slightly mobile

K_foc (mL g⁻¹)

2461

¹/_n

0.88

Notes and range

EU dossier K_f range 19.6-49.3; K_foc range 1766-3751 mL g⁻¹, ¹/_n range 0.79-0.96, n-5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.83

Calculated

Low leachability

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

Value

1.50 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

2.5

Calculated using the Atkinson method. Assumed 5.0E+05 OH/cm³

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

170

Whole fish

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

1H-1,2,4-triazol-1-ylacetic acid (Ref: CGA 142856)

Minor fraction

0.06

4-[2-hydroxy-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butoxy]-benzoic acid (Ref: BUE 2684)

Minor fraction

3-(1H-1,2,4-triazol-1-yl)-alanine (Ref: CGA 131013)

Minor fraction

1,2,4-triazole (Ref: CGA 71019)

Major fraction

0.440

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

α-(1,1-dimethylethyl)-β-[(4'-hydroxy[1,1'-biphenyl]-4-yl)oxy]-1H-1,2,4-triazole-1-ethanol

4-hydroxy btertanol

Surface water

0.24

butyl acetyl triazole

Surface water

0.08

salicylic acid

Surface water

bitertanol ketone

Surface water

3,3-dimethyl-hydroxy-butanol

Surface water

3,3-dimethyl-hydroxy-butyric acid

Surface water

bitertanol malonyl glucoside

Plant

3-(1H-1,2,4-triazol-1-yl)-alanine (Ref: CGA 131013)

triazole alanine

Plant

1,2,4-triazole (Ref: CGA 71019)

Surface water; Sediment

4'-{[(1RS,2RS;1RS,2SR)-2-hydroxy-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butyl]oxy}biphenyl-4-ol

p-hydroxy bitertanol

Animal (Milk, Fat, Eggs)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

8.16

Rat

High

(ppm diet)

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

776

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

222 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

0.8

Colinus virginianus

High

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

> 1000

Eisenia foetida

Low

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

2.7

Eisenia foetida 56 day

Moderate

Soil micro-organisms

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

Dose: 11.0 mg kg⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 6840

Amaranthus retroflexus
Vegetative vigour, ER₅₀
as g ha⁻¹

> 6840

Amaranthus retroflexus
Seedling emergence, ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 200

Apis mellifera

Low

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

> 104.4

Apis mellifera

Low

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

Chronic

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 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

> 1000

Aphidius rhopalosiphi

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

> 6000

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

2.14

Oncorhynchus mykiss

Moderate

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

0.0076

Oncorhynchus mykiss

High

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

> 3.22

Danio rerio

Moderate

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

4.46

Daphnia magna

Moderate

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

0.15

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)

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

0.56

Chironomus riparius

Moderate

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

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

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

1.38

Scenedesmus subspicatus

Moderate

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

Unknown species

Moderate

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.25

Rat 4 hr

Other Mammal toxicity endpoints

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

0.003

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

0.01

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

Not applicable

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

0.01

Dermal penetration studies (%)

3-17

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risks for bystanders

Occupational

No unacceptable risks for operators or other farm workers identified

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=3.0 µg l⁻¹

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

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

Possible liver, adrenals & thymus toxicant
Endocrine issues - Inhibition of aromatase activity, decrease of strogens production

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health; H302, H330
Environment: H411

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

bitertanol

French

bitertanol

German

Bitertanol

Danish

bitertanol

Italian

bitertanolo

Spanish

bitertanol

Greek

Polish

bitertanol

Swedish

bitertanol

Hungarian

bitertanol

Dutch

Norwegian

Record last updated:	23/08/2024
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