Tetraconazole (Ref: M 14360)

Tetraconazole (Ref: M 14360)	Last updated: 12/01/2021
(Also known as: tetraconazol)

GENERAL INFORMATION

Description

A fungicide used to control a range of fungal infections such as Septoria, and Rhynchosporium on cereals, sugarbeet and other crops

Example pests controlled

Powdery mildew; Rusts; Bunt; Loose smut; Scab; Leafspot

Example applications

Sugarbeet; Wheat; Grapes; Apple

Efficacy & activity

Corn/Grey leaf spot=High; Corn/Southern rust=Moderate; Soybean/Anthracnose=Moderate; Soybean/Brown spot=High; Soybean/Rust=High; Soybean/White mould=Moderate

Availability status

Current

Introduction & key dates

circa 1990

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

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

France/Germany

Date EC 1107/2009 inclusion expires

31/12/2021

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

Australia, USA

Chemical structure

Isomerism

A chiral molecule. The technical material is an isomeric mixture of the R (+) and S (-) forms.

Chemical formula

C₁₃H₁₁Cl₂F₄N₃O

Canonical SMILES

C1=CC(=C(C=C1Cl)Cl)C(CN2C=NC=N2)COC(C(F)F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

LQDARGUHUSPFNL-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H11Cl2F4N3O/c14-9-1-2-10(11(15)3-9)8(4-22-7-20-6-21-22)5-23-13(18,19)12(16)17/h1-3,6-8,12H,4-5H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Triazole

Minimum active substance purity

950 g kg⁻¹ racemic mixture

Known relevant impurities

EU dossier - toluene 13g kg⁻¹

Substance origin

Synthetic

Mode of action

Systemic with protectant, eradicant and curative properties. Sterol biosynthesis inhibitor, acts mainly on the vegetative stages of fungi by blocking the mycelial growth either inside or on the surface of the host plant.

CAS RN

112281-77-3

EC number

407-760-6

CIPAC number

726

US EPA chemical code

120603

PubChem CID

80277

Molecular mass

372.15

PIN (Preferred Identification Name)

rac-1-[(2R)-2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole

IUPAC name

(RS)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl 1,1,2,2-tetrafluoroethyl ether

CAS name

1-(2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl)-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 viscous liquid

Related substances & organisms

ethylene glycol

Formulations

Property

Value

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

Trident
Eminent 40ME

Example products using this active

AgriGuard
Isagro
Sipcam

Formulation and application details

Formulations include microemulsions

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

156.6

Moderate

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

300000

Xylene

300000

Acetone

300000

Ethyl acetate

15000

n-Hexane

Melting point (°C)

-29.2

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

235

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.63 X 10⁰³

Calculated

Log P

3.56

High

Bulk density (g ml⁻¹)

1.459

Dissociation constant pKa) at 25 °C

0.65

pKa range 0.8-0.5, Strong acid

Vapour pressure at 20 °C (mPa)

0.18

Low volatility

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

3.60 X 10^-04

Non-volatile

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

281nm < 310, No significant aborption at >290 nm

Surface tension (mN m⁻¹)

49.94

at 20°C 111.8mg l⁻¹

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)

83.8

Moderately persistent

DT₅₀ (field)

430

Very persistent

DT₉₀ (lab at 20 °C)

Stable

DT₉₀ (field)

1428

DT₅₀ modelling endpoint

Note

EU dossier states no degradation during lab studies, field studies DT₅₀ range 136-1688 days, DT₉₀ range 453-5606 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

5.5

Note

Published literature RL₅₀ range 4.0-7.0 days, 7 field & undercover grown crops, various matrices, n=11

Aqueous photolysis DT₅₀ (days) at pH 7

Value

217

Stable

Note

Not expected to be an important degradation rate

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

Value

Stable

Note

Stable pH 4 to pH 9, 120 hrs

Water-sediment DT₅₀ (days)

340

Slow

Water phase only DT₅₀ (days)

Moderately 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

145

Slightly mobile

K_foc

1152

¹/_n

0.92

Notes and range

EU dossier kf range 8.53-548.9 mL g⁻¹, K_foc range 531-1922 mL g⁻¹, ¹/_n range 0.88-0.99, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.47

Calculated

Transition state

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

Value

1.63 X 10^-01

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propanoic acid (Ref: M14360-acid)

Soil

0.089

Minor fraction, relevancy unknown

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

Soil

0.049

Minor fraction, relevancy unknown

2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-ol (Ref: M14360-alcohol)

Soil

0.470

Major fraction, relevancy unknown

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

35.7

Whole fish

Low potential

CT₅₀ (days)

0.189

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1031

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 0.8

Rat

High

(ppm diet)

> 10

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

Birds - Acute LD₅₀ (mg kg⁻¹)

132

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

55.5 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

4.3

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.3

Pimephales promelas growth

Moderate

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

3.0

Daphnia magna

Moderate

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

0.19

Daphnia magna

Moderate

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

0.42

Mysidopsis bahia

Moderate

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

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

4.45

Chironomus riparius

Moderate

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

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

0.52

Lemna gibba

Moderate

Non-target plants

> 112

10 tested species
Vegetative vigour, ER₅₀
as g ha⁻¹

> 112

10 tested species
Seedling emergence, ER₅₀
as g ha⁻¹

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

2.4

Ankistodesmus bibaiamus<

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)

Moderate

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

> 130

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)

Eisenia foetida

Moderate

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

8.2

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Harmless

[Dose: 40 g ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Harmful

[Dose: 40 g ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 0.5 mg kg⁻¹ soil 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)

1031

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.66

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.004

Rat SF=100

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

0.05

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)

0.03

Dog SF=100

Dermal penetration studies (%)

1.0-20.0

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified with PPE/PPC

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Liver toxicant
USEPA - possible human carcinogen at high doses

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H302, H332
Environment: H411

EC Risk Classification

Xn - Harmful: R20/22
N - Dangerous for the environment: R51, R53

EC Safety Classification

S2, S36, S61

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

tetraconazole

French

tetraconazole

German

Tetraconazol

Danish

tetraconazol

Italian

tetraconazolo

Spanish

tetraconazol

Greek

Polish

tetrakonazol

Swedish

Hungarian

tetrakonazol

Dutch

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