Prothioconazole (Ref: JAU 6476 )

Prothioconazole (Ref: JAU 6476 )	Last updated: 12/01/2021
(Also known as: AMS 21619)

GENERAL INFORMATION

Description

A fungicide for use both as a seed treatment and foliar spray to treat a variety of diseases in cereals

Example pests controlled

Phoma leaf spot; Phoma stem canker; Powdery mildew; Yellow rust; Brown rust; Tan spot; Septoria leaf and glume blotch

Example applications

Cereals including barley, rye, wheat, oats

Efficacy & activity

Wheat/Eyespot=High; Wheat/Mildew=Moderate; Wheat/Septoria=Moderate; Wheat/Yellow rust=High; Wheat/Brown rust=Low; Wheat/Ear blight=Moderate; Barley/Rhynchosporium=Moderate; Barley/Mildew=Moderate; Barley/Rust=Low; Barley/Net blotch=Moderate; Barley/Ramularia=Moderate; Corn/Northern leafblight=Moderate; Corn/Rust=Moderate; Corn/Eyespot=High; Soybean/Rust=High; Soybean/White mould=Moderate

Availability status

Current

Introduction & key dates

circa 2002

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

32/07/2024

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

UK/France

Date EC 1107/2009 inclusion expires

32/07/2021

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

Chemical structure

Isomerism

A chiral molecule. The technical material is a racemate comprising equal amounts of (R)- and (S)-prothioconazole.

Chemical formula

C₁₄H₁₅Cl₂N₃OS

Canonical SMILES

C1CC1(C(CC2=CC=CC=C2Cl)(CN3C(=S)N=CN3)O)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

MNHVNIJQQRJYDH-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H15Cl2N3OS/c15-11-4-2-1-3-10(11)7-14(20,13(16)5-6-13)8-19-12(21)17-9-18-19/h1-4,9,20H,5-8H2,(H,17,18,21)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
prothioconazole	Unstated isomer

General status

Pesticide type

Fungicide

Substance group

Triazolinthione

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - Toluene 5g kg⁻¹; other substances, including prothioconazole-desthio & triazole-1-ethanol, at undefined levels

Substance origin

Synthetic

Mode of action

Systemic with protective, curative and eradicative action. Long lasting activity. Sterol biosynthesis inhibitor.

CAS RN

178928-70-6

EC number

CIPAC number

745

US EPA chemical code

1133961

PubChem CID

6451142

Molecular mass

344.26

PIN (Preferred Identification Name)

IUPAC name

(RS)-2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-1,2,4-triazole-3-thione

CAS name

2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione

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

White to beige crystalline powder

Related substances & organisms

clothianidin

tebuconazole

triazoxide

fluoxastrobin

spiroxamine

tebuconazole

Formulations

Property

Value

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

Cello
Fandango
Helix
Jaunt
Kestrel
Proline
Rivet
Aviator Xpro

Example products using this active

AgriGuard
Bayer CropScience
Clayton
Makhteshim
Standon

Formulation and application details

Often supplied as an emuslifiable concentrate that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

22.5

Low

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

215000

Ethyl acetate

280000

Acetone

n-Heptane

8000

Xylene

Melting point (°C)

140.3

Boiling point (°C)

No boiling point under normal conditions

Degradation point (°C)

220

Flashpoint (°C)

403

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

1.00 X 10⁰²

Calculated

Log P

2.0

Low

Bulk density (g ml⁻¹)

1.36

Dissociation constant pKa) at 25 °C

6.9

Weak acid

Vapour pressure at 20 °C (mPa)

7.4 X 10^-06

Low volatility

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

1.1 X 10^-08

Non-volatile

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

Neutral: 202nm=26235, 216nm=13521, 255nm=11850
pH2: 202nm=28193, 216nm=13561, 255nm=12568
pH10: 219nm=14261, 248nm=8972

Surface tension (mN m⁻¹)

67.4

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

14.1

Non-persistent

DT₅₀ (lab at 20 °C)

0.44

Non-persistent

DT₅₀ (field)

0.77

Non-persistent

DT₉₀ (lab at 20 °C)

14.1

Non-persistent

DT₉₀ (field)

4.71

DT₅₀ modelling endpoint

1.8

worse case field value

Note

EU 2018 dossier lab studies DT₅₀ range 0.04-1.1 days, DT₉₀ range 0.9-46.9 days, Soils = 4; Field studies DT₅₀ range 0.49-1.4 days, DT₉₀ range 3.9-5.9 days, Soils=8

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

2.1

Moderately fast

Note

Data for sterile solution pH7 simulated sunlight equivalent to DT₅₀ ~9 days solar summer conditions

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

Value

Stable

Note

Stable pH 4 to pH 9 at 25 and 50 °C

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

15.2

Slightly mobile

K_oc

1765

Notes and range

Freundlich

K_f

44.2

Slightly mobile

K_foc

2556

¹/_n

0.88

Notes and range

EU dossier data for S-methyl variant K_f range 15.6-64.1 mL g⁻¹, K_foc range 1974-2995 mL g⁻¹, ¹/_n range 0.85-0.91, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.07

Calculated

Low leachability

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

Value

7.17 X 10^-05

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

2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(4,5-dihydro-5-methylthio-1,2,4-triazolyl-1)-propan-2-ol

Soil

0.146

Major fraction, Relevant

alpha-(1-chlorocyclopropyl)-alpha-o(2-chlorophenyl)methyl-1H-1,2,4-triazole-1-ethanol

Soil

0.494

Major fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

43.9

Low potential

CT₅₀ (days)

0.47

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 6200

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 25

Dog

High

(ppm diet)

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

95.6

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Anas platyrhynchos

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

Anas platyrhynchos NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.83

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.308

Oncorhynchus mykiss

Moderate

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

1.3

Daphnia magna

Moderate

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

0.56

Daphnia magna

Moderate

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

> 1,01

Americamysis bahia

Low

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

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

9.14

Chironomus riparius

Moderate

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

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

> 0.18

Lemna gibba

Moderate

Non-target plants

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

2.18

Pseudokirchneriella subcapitata

Moderate

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

2.92

Pseudokirchneriella subcapitata

Low

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)

> 71

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)

> 100

Bombus terrestris

Low

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)

> 1000

Eisenia foetida

Low

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

1.33

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

98.1

48 hour mortality
Aphidius rhopalosiphi as ml Aviator EC 225/ha

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

402

>, mortality
Typhlodromus pyri as ml Aviator EC 225/ha

% Effect

Soil micro-organisms

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

Dose: 2 kg ha⁻¹ 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)

> 6200

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.99

Rat

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)

0.8

Rat SF=100

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

0.8

Rat SF=100

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

0.25

Mice SF=100

Dermal penetration studies (%)

5-35

concentration and formulation dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified for intended uses

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit

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 & kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Environment: H400, H410, H411

EC Risk Classification

Reproduction risk category 3: R63
Xn - Harmful: R43
N - Dangerous for the environment: R51, R53

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

prothioconazole

French

prothioconazole

German

Prothioconazole

Danish

prothioconazol

Italian

protioconazolo

Spanish

protioconazol

Greek

Polish

protiokonazol

Swedish

protiokonazol

Hungarian

Dutch

prothioconazool

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