Ipconazole (Ref: KNF 317)

Ipconazole (Ref: KNF 317)	Last updated: 21/10/2020
(Also known as: ipoconazole)

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, Japan

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/08/2024

UK LERAP status

None (may vary with mixtures)

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

31/08/2024

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

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 group

Triazole

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

CIPAC number

789

US EPA chemical code

125628

PubChem CID

86211

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 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 crystals

Formulations

Property

Value

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

Crusoe
Vortex
Rancona

Example products using this active

Chemtura Europe
Kureha Corp

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)

Not expected to self ignite; Not highly flammable

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

2.00 X 10⁰⁴

Calculated

Log P

4.3

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

Slightly mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.237

Relevant, Major fraction

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

triazole alanine

Plants

Ref: KNF-317-M-21

triazole acetic acid

Plants

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

350

Threshold for concern

CT₅₀ (days)

Not available

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⁻¹ BW/day

Colinus virginianus

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

4.3

Colinius virginianus NOEL

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 1.5

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 0.76

Oncorhynchus mykiss LOAEC

Moderate

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

1.7

Daphnia magna

Moderate

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

0.13

Daphnia magna LOAEC

Moderate

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)

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

3.25

Chironomus riparius

Moderate

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

Non-target plants

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

0.62

Pseudokirchneriella subcapitata

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)

> 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)

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)

298.8

Eisenia foetida corr

Moderate

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

0.39

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

17.4

7-day
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

35.1

48 hours
Aphidius rhopalosphophi

% Effect

Soil micro-organisms

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

Dose: 2.88mg 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)

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)

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

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

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

CLP classification 2013

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

EC Risk Classification

Reproduction risk category 3: R63
Xn - Harmful: R22
Xi - Irritant: R48

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

ipconazole

French

German

Danish

Italian

Spanish

Greek

Polish

ipkonazol

Swedish

Hungarian

Dutch

Record last updated:	21/10/2020
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