Propiconazole (Ref: CGA 64250)

Propiconazole (Ref: CGA 64250)	Last updated: 03/03/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A systemic fungicide with a broad range of activity and a wide range of agricultural cropping applications

Example pests controlled

Diseases caused by Erysiphe graminis; Leptosphaeria nodorum; Pseudocerosporella herpotrichoides; Puccinia spp.; Pyrenophora teres; Rhynchosporium secalis; Septoria spp.

Example applications

Mushrooms; Corn; Wild rice; Peanuts; Amonds; Sorghum; Oats; Pecan; Fruit including apricots, plums, prunes, peaches & nectarines

Efficacy & activity

Wheat/Eyespot=Low; Wheat/Mildew=Low; Wheat/Septoria=Low; Wheat/Rust=Low; Barley/Rust=Low; Corn/Northern Leaf blight=Moderate; Corn/Rust=Moderate; Corn/Eyespot=High; Soybean/Blight=Low; Soybean/Anthracnose=High; Soybean/Brown spot=Moderate; Soybean/Rust=High

Availability status

Current

Introduction & key dates

1980

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Finland/UK

Date EC 1107/2009 inclusion expires

Expired

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

Chemical structure

Isomerism

A molecule with 2 chiral features leading to four stereoisomers.

Chemical formula

C₁₅H₁₇Cl₂N₃O₂

Canonical SMILES

CCCC1COC(O1)(CN2C=NC=N2)C3=C(C=C(C=C3)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

STJLVHWMYQXCPB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H17Cl2N3O2/c1-2-3-12-7-21-15(22-12,8-20-10-18-9-19-20)13-5-4-11(16)6-14(13)17/h4-6,9-10,12H,2-3,7-8H2,1H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
propiconazole	Unstated isomer

General status

Pesticide type

Fungicide

Substance group

Triazole

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with curative and protective action, works via the demethylation of C-14 during ergosterol biosynthesis

CAS RN

60207-90-1

EC number

262-104-4

CIPAC number

408

US EPA chemical code

122101

PubChem CID

43234

Molecular mass

342.22

PIN (Preferred Identification Name)

IUPAC name

(2RS,4RS;2RS,4SR)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole

CAS name

1-((2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl)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

Clear to pale yellow viscous liquid depending on the ratio of isomers

Related substances & organisms

cyproconazole

prochloraz

chlorothalonil

cis-propiconazole

trans-propiconazole

Formulations

Property

Value

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

Bumper 250EC
Cherokee
Menara
Tilt
Mantis
Banner Maxx

Example products using this active

Greencrop
Makhteshim-Agan
Syngenta
Ciba Geigy

Formulation and application details

Often supplied as emulsifiable concentrates or wettable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

150

Moderate

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

1585

n-Heptane

Miscible

Acetone

Miscible

Methanol

Miscible

Xylene

Melting point (°C)

-23

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

355

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

5.25 X 10⁰³

Calculated

Log P

3.72

High

Bulk density (g ml⁻¹)

1.09

Dissociation constant pKa) at 25 °C

1.09

Very weak base

Vapour pressure at 20 °C (mPa)

0.056

Low volatility

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

9.20 X 10^-05

Non-volatile

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

220 nm = 11666

Surface tension (mN m⁻¹)

55.0

at 20 °C 90%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

71.8

Moderately persistent

DT₅₀ (lab at 20 °C)

71.8

Moderately persistent

DT₅₀ (field)

35.2

Moderately persistent

DT₉₀ (lab at 20 °C)

344.8

Persistent

DT₉₀ (field)

478

DT₅₀ modelling endpoint

Note

EU 2016 dossier lab studies DT₅₀ range 26.6-115 days, DT₉₀ range 107-1000 days, Soils=12; field studies DT₅₀ range 15.3-96.3 days, DT₉₀ range 108-525 days, Soils=6

Dissipation rate RL₅₀ on plant matrix

Value

6.4

Note

Published literature RL₅₀ range 4.6-8.2 days, 2 field crops, various matrices, n=2

Dissipation rate RL₅₀ on and in plant matrix

Value

7.4

Note

Published literature RL₅₀ range 1.0-16.9 days, 7 field crops, various matrices, n=10

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Not a significant degradation route

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

Value

53.5

Moderately persistent

Note

Water-sediment DT₅₀ (days)

561

Stable

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

33.7

Slightly mobile

K_oc

1086

Notes and range

EU 2003 dossier K_oc range 382-1789, Soils=9

Freundlich

K_f

15.0

Slightly mobile

K_foc

955

¹/_n

0.86

Notes and range

EU 2016 dossier: K_f range 1.20-59.0 mL g⁻¹, K_foc range 387-1817 mL g⁻¹, ¹/_n range 0.81-0.89, Soils=9; Literature data: K_f range 27-1277 mL g⁻¹, K_foc range 1440-3387 mL g⁻¹, ¹/_n range 0.75-0.88, Soils=3 (R4)

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.58

Calculated

Low leachability

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

Value

4.25 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

0.430

Major fraction, Relevant

(2S,4S-2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-carboxylic acid (Ref: SYN 547889)

Soil

0.154

Major fraction, Relevant

1H-1,2,4-triazole-1-ethanol, alpha-(2,4-dichlorophenyl)- 2-(1,2,4) triazol-1-yl-ethanol (Ref: CGA 91305)

Soil

0.08

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

NOA 436613

Soil

0.123

2-(2,4-dichlorophenyl)-á-ethyl-2-(1H-1,2,4-riazol-1-yl-methyl)-1,3-dioxolane-4-methanol
Note: CAS Number:119725-85-8

CGA136735

Plant

3-chloro-4-(4-propyl-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-2-yl)-phenol

GB-XLIII-42-1

Plant

1,3-dioxolane-4-ethanol, 2-(2,4-dichlorophenyl)-á-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-
Note: CAS Number 104390-57-0

CGA118244; CSAA107724

Plant; Rat; Livestock

3-[2-(2,4-dichlorophenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-yl]-2-hydroxy-propionic acid

SYN542636

Lactating goat

3-[2-(2,4-dichlorophenyl)-2-[1,2,4]triazol-1-yl-methyl-[1,3]dioxolan-4-yl]-propan-1-ol

CGA118245

Wheat; Lactating goat

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

116

Whole fish

Threshold for concern

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

550

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

2.7

Mice

High

(ppm diet)

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

43.7

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2510

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Anas platyrhynchos

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

25.5

Anas platyrhynchos NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

2.6

Leiostomus xanthurus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.068

Oncorhynchus mykiss

Moderate

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

10.2

Daphnia magna

Moderate

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

0.31

Daphnia magna

Moderate

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

0.37

Americamysis bahia

Moderate

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

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

8.0

Chironomus riparius

Moderate

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

25.0

Chironomus riparius

Moderate

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

4.9

Lemna gibba

Moderate

Non-target plants

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

0.093

Navicula seminulum 11 day

Moderate

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

0.32

Unknown species

Moderate

Honeybees (Apis spp.)

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

> 100

Low

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

> 100

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)

33.3

Osmia lignaria

Moderate

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)

686

Moderate

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

0.833

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

100

Mortality [Dose: 0.25 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

100

Beneficial capacity [Dose: 0.125 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 6.7 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)

550

Rat

Moderate

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

4000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.8

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.04

Rat SF=100

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

0.3

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)

9-14

Rat SF=100

Dermal penetration studies (%)

0.9-2.4

concentration 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

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

USEPA - possible human carcinogen, EU - unlikely to pose a hazard to humans
Possible liver toxicant
Endocrine issues - Weak estrogen and aromatase activity inhibition

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H302, H317, H360D
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22, R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S36/37, S46, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

propiconazole

French

propiconazol

German

Propiconazol

Danish

propiconazol

Italian

propiconazolo

Spanish

propiconazol

Greek

Polish

propikonazol

Swedish

propikonazol

Hungarian

propikonazol

Dutch

propiconazool

Record last updated:	03/03/2021
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