Epoxiconazole (Ref: BAS 480F)

Epoxiconazole (Ref: BAS 480F)	Last updated: 18/01/2021
(Also known as: epoxyconazole)

SUMMARY

Epoxiconazole is a broad-spectrum fungicide that has regulatory approval for use in the EU. It has a low aqueous solubility and is relatively volatile. It may persist in both soil and water systems. It is not highly toxic to mammals and is not expected to bioaccumulate. Epoxiconazole is moderately toxic to birds, honeybees, earthworms and most aquatic organisms.

GENERAL INFORMATION

Description

A broad-spectrum fungicide for control of diseases caused by Ascomycetes, Basidiomycetes and Deuteromycetes

Example pests controlled

Black & yellow Sigatoka, Coffee rust; Septoria leaf blotch; Stem rust

Example applications

Sugarbeet; Cereals including wheat, barley, rye, oats and triticale; Coffee; Bananas

Efficacy & activity

Wheat/Eyespot=Low; Wheat/Mildew=Low; Wheat/Septoria=Moderate; Wheat/Rust=High; Wheat/Ear blight=Low; Barley/Rhynchosporium=Low; Barley/Mildew=Low; Barley/Rust=Moderate; Barley/Net blotch=Low; Barley/Ramularia=Low

Availability status

Current

Introduction & key dates

1993, first registered

UK regulatory status

UK COPR regulatory status

Phasing out

Date COPR inclusion expires

Not applicable

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

UK/Poland

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

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 molecule with 2 chiral centres resulting in four stereoisomers

Chemical formula

C₁₇H₁₃ClFN₃O

Canonical SMILES

C1=CC=C(C(=C1)C2C(O2)(CN3C=NC=N3)C4=CC=C(C=C4)F)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

FEVYAAHIKWPJNV-TYDMEHBZSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H13ClFN3O/c18-15-4-2-1-3-14(15)16-17(23-16,9-22-11-20-10-21-22)12-5-7-13(19)8-6-12/h1-8,10-11,16H,9H2/t16-,17-/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Triazole

Minimum active substance purity

920 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Preventative and curative action. Sterol biosynthesis inhibitor.

CAS RN

135319-73-2

Alternative/old CAS RN

formerly 106325-08-0

EC number

406-850-2

CIPAC number

609

US EPA chemical code

123909

PubChem CID

3317081

Molecular mass

329.76

PIN (Preferred Identification Name)

rac-1-{[(2R,3S)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole

IUPAC name

(2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole

CAS name

rel-1-(((2R,3S)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiranyl)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

Colourless crystalline solid

Related substances & organisms

boscalid

carbendazim

dimoxystrobin

kresoxim-methyl

metrafenone

pyraclostrobin

Formulations

Property

Value

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

Epic
Opus
Splice
Swing Gold
Tango super
Venture

Example products using this active

AgriGuard
BASF
Bayer Environ
Landgold
Standon

Formulation and application details

Often supplied as a soluble concentrate which is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

7.1

Low

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

100000

Ethyl acetate

140000

Acetone

28800

Ethanol

40000

Toluene

Melting point (°C)

136.2

Boiling point (°C)

310

Degradation point (°C)

310

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.00 X 10⁰³

Calculated

Log P

3.3

High

Bulk density (g ml⁻¹)

1.38

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

3.5 X 10^-04

Low volatility

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

1.649 X 10^-05

Non-volatile

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

204nm = 32000, 263nm = 390; No absorption above 290nm

Surface tension (mN m⁻¹)

72.9

at 20°C 6.4mg l⁻¹

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

353.5

Persistent

DT₅₀ (lab at 20 °C)

353.5

Persistent

DT₅₀ (field)

97.7

Moderately persistent

DT₉₀ (lab at 20 °C)

1000

Very persistent

DT₉₀ (field)

2960

DT₅₀ modelling endpoint

Note

EU 2019 dossier lab studies DT₅₀ (normalised) range 127.1-1000 days, DT₉₀ (measured) > 1000 days, Soils=20. Field studies DT₅₀ (measured) range 0.75-247.8 days, DT₉₀ (measured) range 183.7->10,000 days, Soils=12; Other studies: lab DT₅₀ range 224-2236 days, field range 52-226 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

11.8

Note

Published literature RL₅₀ range 3.1-26.5 days, 5 field crops, various matrices, n=5

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 9 at 25 °C, some hydrolysis at elevated temperatures

Water-sediment DT₅₀ (days)

103.6

Slow

Water phase only DT₅₀ (days)

1000

(default)

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

12.2

Slightly mobile

K_foc

894

¹/_n

0.86

Notes and range

EU 2019 dossier K_f range 8.24-17.8 mL g⁻¹, K_foc range 702-1962 mL g⁻¹, ¹/_n range 0.83900.882, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.09

Calculated

Transition state

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

Value

9.22 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.066

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

triazole alanine

Plant

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

TAA

Plant

triazoly hydroxyl propionic acid (Ref: 480M50)

THPA

Plant

triazole acetic acid

Plant

1-[(2Z)-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2 propenyl]-1H-1,2,4-triazole (Ref: BF480-entriazole)

Water/sediment; Soil

1-(2-chlorophenyl)-2-(4-fluorophenyl)-1-hydroxy-3-(1H-1,2,4-triazol-1-yl)propane (Ref: BF480-alcohol)

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

0.8

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

3160

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

7.5

Rat

High

(ppm diet)

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

2.3

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 907 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

0.91

Colinius virginianus NOAEL

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.92

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.01

Oncorhynchus mykiss 28 day

Moderate

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

> 3.13

Daphnia magna

Moderate

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

0.63

Daphnia magna

Moderate

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

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

0.0625

Chironomus riparius emergence

High

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

>= 0.00625

Chironomus riparius

High

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

0.03

Chironomus riparius dry sediment

High

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

0.014

Lemna gibba

Moderate

Non-target plants

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

> 10.69

Pseudokirchneriella subcapitata

Low

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

0.0078

Pseudokirchneriella subcapitata

Moderate

Honeybees (Apis spp.)

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

> 100

Apis mellifera

Low

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

> 83

Apis mellifera

Moderate

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)

> 200

Bombus terrestris

Low

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

> 165.5

Bombus terrestris

Low

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)

>= 3.24

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

3.58

Mortality. 48hr LR₅₀
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

0.057

Mortality 7d LR₅₀
Typhlodromus pyri

% Effect

Soil micro-organisms

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

28 days

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)

3160

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.3

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.008

Mouse SF=100

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

0.023

Rat SF=100

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

0.011

Rat SF=200

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

0.008

Rat SF=100

Dermal penetration studies (%)

2-36

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Acceptable risk for proposed uses

Occupational

Acceptable risk for proposed uses

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible liver toxicant
USEPA - probable human carcinogen
Endocrine issues - Inhibition of aromatase activity, decrease of estrogen production

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H351, H360Df
Environment: H411

EC Risk Classification

Carcinogen category 3: R40
Reproduction risk category 3: R62, R63
N - Dangerous for the environment: R51, R53

EC Safety Classification

S2, S36/37, S46, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3077 or 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

epoxiconazole

French

epoxiconazole

German

Epoxiconazol

Danish

epoxiconazol

Italian

epossiconazolo

Spanish

epoxiconazol

Greek

epoxiconazole

Polish

epoksykonazol

Swedish

Hungarian

epoxikonazol

Dutch

epoxiconazool

Record last updated:	18/01/2021
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