Ipconazole (Ref: KNF 317)

Ipconazole (Ref: KNF 317)	Last updated: 21/08/2024
(Also known as: ipoconazole)

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 High alert: Persistent; Potential for particle bound transport: High	Ecotoxicity High alert: Birds chronic ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Genotoxic; Reproduction/development effects

GENERAL INFORMATION

Description

Used to control a range of soil and seed borne seed diseases in a wide range of crops including root and leafy vegetables, cereals and rice

Example pests controlled

Various fungal pathogens including Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes

Example applications

Root vegetables including beet, carrot, parsnip and radish; Leafy vegetables including celery, fennel, lettuce, spinach and Swiss chard; Brassicas including broccoli, cabbage and kale; Rice; Cereal grains, Cotton; Sunflower

Efficacy & activity

Availability status

Current

Introduction & key dates

1994, registered Japan

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/11/2025

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Belgium/France

Date EC 1107/2009 inclusion expires

Not applicable

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

USA

Chemical structure

Isomerism

Ipconazole is a chiral molecule with 3 stereocenters and 4 diastereoisomers, however the commercial material is a mixture of just two (cis-,cis- and cis-, trans) in the ratio 9 :1.

Chemical formula

C₁₈H₂₄ClN₃O

Canonical SMILES

CC(C)C1CCC(C1(CN2C=NC=N2)O)CC3=CC=C(C=C3)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

QTYCMDBMOLSEAM-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H24ClN3O/c1-13(2)17-8-5-15(9-14-3-6-16(19)7-4-14)18(17,23)10-22-12-20-11-21-22/h3-4,6-7,11-13,15,17,23H,5,8-10H2,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Triazole fungicide

Minimum active substance purity

955 g kg⁻¹

Known relevant impurities

EU dossier - ipconazole cc 875-930g kg⁻¹; ipconazole ct 65-95g kg⁻¹

Substance origin

Synthetic

Mode of action

Systemic, broad-spectrun, inhibits sterol synthesis in fungi.

CAS RN

125225-28-7

EC number

603-038-1

CIPAC number

798

US EPA chemical code

125628

PubChem CID

86211

CLP index number

603-237-00-3

Molecular mass

333.9

PIN (Preferred Identification Name)

(1E,2E,5E)-2-[(4-chlorophenyl)methyl]-5-(propan-2-yl)-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol

IUPAC name

(1RS,2SR,5RS;1RS,2SR,5SR)-2-(4-chlorobenzyl)-5-isopropyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol

CAS name

2-[(4-chlorophenyl)methyl]-5-(1-methylethyl)-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol

Other status information

PAN listed Highly Hazardous Chemical

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

Formulations

Property

Value

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

Chemtura Europe
Kureha Corp

Example products using this active

Crusoe
Vortex
Rancona

Formulation and application details

Usually available as a microemulsion but also available as emulsifiable concentrates and suspension concentrates. Often used as a seed dressing.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

9.34

Low

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

570000

Acetone

425000

1,2-Dichloroethane

428000

Ethyl acetate

679000

Methanol

Melting point (°C)

Boiling point (°C)

400

Degradation point (°C)

Flashpoint (°C)

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

2.00 X 10⁰⁴

Calculated

Log P

4.3

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.2

Dissociation constant pKa) at 25 °C

-5.43

Vapour pressure at 20 °C (mPa)

0.003

Low volatility

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

3.0 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral: 276nm=315
Acidic: 276nm=304
Basic: 276nm=312

Surface tension (mN m⁻¹)

56.5

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)

213

Persistent

DT₅₀ (field)

131

Persistent

DT₉₀ (lab at 20 °C)

709

Very persistent

DT₉₀ (field)

390

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 170-294 days, DT₉₀ range 564-977 days, Field studies DT₅₀ range 66-228 days, DT₉₀ range 219-757 days; Other sources: DT₅₀ range 330 - 1386 days anaerobic, 136 to 210 days in aerobic soils & 89 to 121 days in paddy fields (F4); Other literature values DT₅₀ range 45-54 days for upland soils and 76-80 days submerged soils (F4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

495

Stable

Note

pH sensitive: pH5 = 330 days, pH7 = 495 days, pH9 = 257 days, all at 25° C

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

Value

(natural sunlight)

Moderately persistent

Note

No degradation in the dark

Water-sediment DT₅₀ (days)

344

Slow

Water phase only DT₅₀ (days)

2.4

Moderately fast

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

Slightly mobile

K_foc (mL g⁻¹)

2431

¹/_n

0.81

Notes and range

K_f range 5.2-108 mL g⁻¹, K_foc range 1724-3124 mL g⁻¹, ¹/_n range 0.78-0.86, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.30

Calculated

Low leachability

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

Value

3.13 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

5.1

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

350

Threshold for concern

CT₅₀ (days)

Not available

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

0.237

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

triazole alanine

Plant

Ref: KNF-317-M-21

triazole acetic acid

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

888

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

> 22

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 962

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 300 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

4.3

Colinus virginianus NOEL

High

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

298.8

Eisenia foetida corr

Moderate

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

0.39

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 2.88 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

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)

> 100

Apis mellifera

Low

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

Chronic

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 48 hr

35.1

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

17.4

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)

> 1.5

Oncorhynchus mykiss

Moderate

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

> 0.76

Oncorhynchus mykiss LOAEC

Moderate

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

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

1.7

Daphnia magna

Moderate

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

0.13

Daphnia magna LOAEC

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)

3.52

Chironomus riparius

Moderate

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

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

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

0.62

Pseudokirchneriella subcapitata

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

888

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.53

Rat

Other Mammal toxicity endpoints

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

0.015

Dog SF=100

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

0.015

Rat SF=200

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

Not applicable

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

0.015

Rat SF=200

Dermal penetration studies (%)

Undiluted & co-applied with water

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low for proposed uses

Occupational

Calculated risks for seed treatment handlers are low

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Extensively metabolised, 70% excreted, mostly in the faeces, within 24 hours.

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

Eye irritant

Phototoxicant

No data found

General human health issues

Possible stomach toxicant
May cause eye damage

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H332, H361, H373
Environment: H400, H410, H411

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

ipconazole

French

German

Danish

Italian

Spanish

Greek

Polish

ipkonazol

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	21/08/2024
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