Triadimenol (Ref: BAY KWG 0519)

Triadimenol (Ref: BAY KWG 0519)	Last updated: 23/08/2024
(Not known by any other names)

SUMMARY

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: Moderately persistent; GUS: Transition state; Drainflow: Slightly mobile	Ecotoxicity High alert: Birds chronic ecotoxicity: High	Human health High alert: Mammals chronic toxicity: High; Endocrine disrupter; Reproduction/development effects

GENERAL INFORMATION

Description

A fungicide for cereals and other crops used to control a range of diseases

Example pests controlled

Powdery mildew; Rusts; Bunts; Smuts; Eyespot

Example applications

Cereals including wheat, rye, triticale, oats, barley; Beet crops; Brassicas; Grapes

Efficacy & activity

Availability status

Current

Introduction & key dates

1978, first reported & marketed

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Spain/Latvia

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

Chemical structure

Isomerism

A chiral molecule. The technical material is a mixture of two diastereoisomeric forms.The ratio of these is usually: diastereoisomers RS + SR: 78-88%; diastereoisomers RR + SS: 12-22%.

Chemical formula

C₁₄H₁₈ClN₃O₂

Canonical SMILES

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

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

BAZVSMNPJJMILC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H18ClN3O2/c1-14(2,3)12(19)13(18-9-16-8-17-18)20-11-6-4-10(15)5-7-11/h4-9,12-13,19H,1-3H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
triadimenol	-
(1R,2S)-(+)-A Triadimenol	-

General status

Pesticide type

Fungicide, Metabolite

Metabolite Type

Soil, Plant

Substance groups

Triazole fungicide; Conazole fungicide

Minimum active substance purity

970 g kg⁻¹ isomer mix

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective with curative, protective and eradicant action. Disrupts membrane function. Sterol biosynthesis inhibitor.

CAS RN

55219-65-3

EC number

259-537-6

CIPAC number

398

US EPA chemical code

127201

PubChem CID

41368

CLP index number

No data found

Molecular mass

295.76

PIN (Preferred Identification Name)

(1E,2E)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

IUPAC name

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

CAS name

β-(4-chlorophenoxy)-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

Colourless crystals

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

triadimefon

Soil

0.9

Major fraction

Formulations

Property

Value

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

Bayer CropScience
Makhteshim-Agan
Mobay

Example products using this active

Baytan Flowable
Bayfidin EC250
Tripod Plus
Silvacur

Formulation and application details

Available in a variety of formulations including emulsifiable concentrates for spray application and flowable concentrates for seed treatments

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)

250000

Dichloromethane

18000

Xylene

140000

2-Propanol

450

n-Heptane

Melting point (°C)

132.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

270

Flashpoint (°C)

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

1.51 X 10⁰³

Calculated

Log P

3.18

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.27

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0005

Low volatility

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

3.5 X 10^-06

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

Negligible

24 hr

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

Surface tension (mN m⁻¹)

54.4

at 20°C 90% soln

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

250

Persistent

DT₅₀ (lab at 20 °C)

136.7

Persistent

DT₅₀ (field)

36.5

Moderately persistent

DT₉₀ (lab at 20 °C)

455.3

Very persistent

DT₉₀ (field)

215.7

DT₅₀ modelling endpoint

Note

EU dossier lab study DT₅₀ range 47.3-158.4 days (normalised), DT₉₀ range 191-591 days; field studies DT₅₀ range 24.1-83.7 days (normalised), DT₉₀ range 76.3-423.9 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

7.4

Note

Literature studies 3.2-11.7 days, field and undercover, 2 crops, various matrices, n-2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

9.0

Moderately fast

Note

Data for continuous irradiation, stable under dark conditions

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

Value

Stable

Note

Stable pH 4 to pH 9 at 20 and 40 °C

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Stable

Sediment phase only DT₅₀ (days)

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)

Slightly mobile

K_oc (mL g⁻¹)

750

Notes and range

Various sources: (1) 500 (H3), (2) 1000 mL g⁻¹ (US3)

Freundlich

K_f (mL g⁻¹)

2.8

Moderately mobile

K_foc (mL g⁻¹)

273

¹/_n

0.890

Notes and range

EU dossier kf range 0.91-5.66, K_foc range 108-702 mL g⁻¹, ¹/_n range 0.841-0.963, Soils=14

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.44

Calculated

Transition state

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

Value

1.35 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

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 0.5E+06 OH/cm³, 24 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

0.42

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

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

Major fraction

1.00

(R,S)-2-amino-3-(1H-1,2,4-triazol-1-yl)propanoic acid

1H-1,2,4-triazol-1-ylacetic acid

(4-chlorophenoxy)(1H-1,2,4-triazol-1-yl)acetic acid

1,2-dihydro-1,2,4-triazol-3-one (is the tautomer of 1H-1,2,4-triazol-3-ol

4-(4-chlorophenoxy)-3-hydroxy-2,2-dimethyl-4-(1H-1,2,4-triazol-1-yl)butanoic acid

4-chlorophenol

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoic acid

triadimenol metabolite M11

Plant

(R,S)-2-amino-3-(1H-1,2,4-triazol-1-yl)propanoic acid

triadimenol metabolite M05

Plant

1H-1,2,4-triazol-1-ylacetic acid

triadimenol metabolite M06

Plant

4-(4-chlorophenoxy)-3-hydroxy-2,2-dimethyl-4-(1H-1,2,4-triazol-1-yl)butyl glucuronide

triadimenol metabolite M23

Animal

1-O-[4-(4-chlorophenoxy)-3-hydroxy-2,2-dimethyl-4-(1H-1,2,4-triazol-1-yl)butanoyl] glucuronide

triadimenol metabolite M30

Animal

4-(4-chlorophenoxy)-2-methyl-4-(1H-1,2,4-triazol-1-yl)butane-1,3-diol

triadimenol metabolite M18

Animal

1-(4-chlorophenoxy)-3-methyl-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol

triadimenol metabolite M31

Animal

4-(4-chlorophenoxy)-3-hydroxy-2,2-dimethyl-4-(1H-1,2,4-triazol-1-yl)butyl glucoside

triadimenol metabolite M12

Plant

1-(4-chlorophenoxy)-4-hydroxy-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

triadimenol metabolite M09

Animal

4-(4-chlorophenoxy)-2,2-dimethyl-4-(1H-1,2,4-triazol-1-yl)butane-1,3-diol

triadimenol metabolite M10; triadimenol-hydroxy

Plant; Animal; Rat

4-(4-chlorophenoxy)-3-hydroxy-2,2-dimethyl-4-(1H-1,2,4-triazol-1-yl)butanoic acid

triadimenol metabolite M02

Animal; Rat

1-(4-chlorophenoxy)-4-hydroxy-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-yl hydrogen sulfate

triadimenol metabolite M28

Animal

4-chlorophenol

triadimenol metabolite M07

Plant

1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-yl glucoside

triadimenol metabolite M15

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

721

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 8

Rat 2 yr

High

(ppm diet)

> 125

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

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 705 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

7.5

Colinus virginianus NOEL

High

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

> 390.5

Eisenia candida corr

Moderate

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

Soil micro-organisms

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

Dose: 1.71 mg kg⁻¹ 100 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

> 500

Folsomia foetida corr

Non-target plants

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)

> 224.8

Apis mellifera

Low

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

Chronic

Notes

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

> 1250

Aphidius rhopalosiphi

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

> 1250

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)

21.3

Oncorhynchus mykiss

Moderate

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

3.13

Oncorhynchus mykiss

Moderate

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

> 50.87

Danio rario Embryo

Moderate

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

Daphnia magna

Moderate

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

0.1

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)

0.1

Chironomus riparius sediment present

Moderate

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

0.667

Chironomus riparius

Moderate

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

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

9.6

Pseudokirchneriella subcapitata

Moderate

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

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

721

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.954

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.05

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)

0.05

Rat SF=100

Dermal penetration studies (%)

2.0-17.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks for intended uses

Occupational

No unacceptable risks for intended uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL expected to deviate from the EU MRL in mid-2023

Drinking Water Standards

Drinking Water MAC (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

May cause dermatitis
Liver toxicant
Estrogenic
US EPA - possible human carcinogen
Endocrine issues - Estrogenic effect

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302

WHO Classification

II (Moderately hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

triadimenol

French

triadimenol

German

Triadimenol

Danish

triadimenol

Italian

triadimenol

Spanish

triadimenol

Greek

Polish

triadimenol

Swedish

Hungarian

triadimenol

Dutch

triadimenol

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