Cyproconazole (Ref: SAN 619)

Cyproconazole (Ref: SAN 619)	Last updated: 31/10/2024
(Also known as: CGA 221949; SAN 751; A-9898A)

SUMMARY

Cyproconazole is a commonly used fungicide. It is moderately soluble in water and readily soluble in many organic solvents. It is a volatile substance. Based on its physico-chemical properties, cyproconazole has a high risk of leaching to groundwater. It can be persistent in both soil and water systems. It is moderately toxic to mammals. It is highly toxic to birds and moderately toxic to most aquatic organisms, earthworms and honeybees.

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; GUS: High leachability	Ecotoxicity High alert: Birds acute ecotoxicity: High; Birds chronic ecotoxicity: High	Human health High alert: Mammals chronic toxicity: High; Endocrine disrupter; Reproduction/development effects

GENERAL INFORMATION

Description

A broad spectrum fungicide for cereals and other field crops used to control Septoria, rust, powdery mildew and other diseases

Example pests controlled

Spetoria; Net blotch; Brown rust; Yellow rust; Eyespot; Powdery mildews; Chocolate spot; Ear disease; Glume blotch

Example applications

Cereals including wheat, barley, oats, rye; Vegetables including peas & beans, asparagus; Oilseed rape; Sugarbeet; Fruit including apples, peach; Almonds

Efficacy & activity

Wheat/Eyespot=Low; Wheat/Mildew=Low; Wheat/Septoria=Low; Wheat/Rust=Moderate-High; Barley/Mildew=Low; Barley/Rust=Moderate; Soybean/Brown spot=High; Soybean/Leaf blight=Moderate; Soybean/Rust=High

Availability status

Current

Introduction & key dates

1986, first reported; 1989, first introduced France & Switzerland

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Withdrawn

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Ireland

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

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

Australia

Chemical structure

Isomerism

A chiral molecule that is an approximately equal mixture of the two diastereomers, each of which is exactly a 1:1 mixture of the enantiomers.

Chemical formula

C₁₅H₁₈ClN₃O

Canonical SMILES

CC(C1CC1)C(CN2C=NC=N2)(C3=CC=C(C=C3)Cl)O

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UFNOUKDBUJZYDE-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H18ClN3O/c1-11(12-2-3-12)15(20,8-19-10-17-9-18-19)13-4-6-14(16)7-5-13/h4-7,9-12,20H,2-3,8H2,1H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
cyproconazole	Unstated isomer

General status

Pesticide type

Fungicide, Other substance

Other bioactivity & uses

Biocide, Wood preservative

Substance groups

Conazole fungicide; Triazole fungicide

Minimum active substance purity

940 g kg⁻¹

Known relevant impurities

EU dossier - may contain diastereomers of cyproconazole

Substance origin

Synthetic

Mode of action

Systemic with protective, curative and eradicant action. Disrupts membrane function. An ergosterol-biosynthesis inhibitor.

CAS RN

94361-06-5

EC number

619-020-1

CIPAC number

600

US EPA chemical code

128993

PubChem CID

86132

CLP index number

650-032-00-X

Molecular mass

291.78

PIN (Preferred Identification Name)

mixture of the 2 enantiomeric pairs rac-(2R,3R)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol and rac-(2R,3S)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol in the ratio 1:1

IUPAC name

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

CAS name

α-(4-chlorophenyl)-α-(1-cyclopropylethyl)-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

Fine white powder

Formulations

Property

Value

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

Bayer CropScience
Dow AgroSciences
Syngenta

Example products using this active

Alto Elite
Cabaret
Caddy 240EC
Cherokee
Excelsior
Menara
Priori Xtra
Quadris Xtra

Formulation and application details

Often supplied as soluble concentrates that are mixed with water and applied as a spray

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)

360000

Acetone

240000

Ethyl acetate

1300

Hexane

410000

Methanol

Melting point (°C)

106.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

299

Flashpoint (°C)

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

1.23 X 10⁰³

Calculated

Log P

3.09

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.26

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.026

Low volatility

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

5.00 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

17.0

Beans 24 hr

Volatilisation is not considered critical for air pollution

From soil surface

Beans 24 hr

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

Neutral solution: 297nm = 0.7
Acidic solution: 295nm = 0.4
Basic solution: 295nm = 0.8

Surface tension (mN m⁻¹)

65.2

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

142

Persistent

DT₅₀ (lab at 20 °C)

142

Persistent

DT₅₀ (field)

129

Persistent

DT₉₀ (lab at 20 °C)

422

Very persistent

DT₉₀ (field)

579

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 44.9-191 days, DT₉₀ range 149-1000 days, field studies DT₅₀ range 62.1-501.2 days, DT₉₀ range 179->1000 days; Other data: DT₅₀ 144 days (DW4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

13.9

Note

Tomato fruit, undercover, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

11.5

Note

Published literature RL₅₀ range 3.5-16.0 days, 5 field crops, various matrices, n=5

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable pH 4 to pH 9, 50 °C

Water-sediment DT₅₀ (days)

1000

Stable

Water phase only DT₅₀ (days)

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

8.7

Moderately mobile

K_foc (mL g⁻¹)

364

¹/_n

0.862

Notes and range

EU dossier kf range 4.1-17.0, K_foc range 173-711 mL g⁻¹, ¹/_n range 0.84-0.90, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.04

Calculated

High leachability

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

Value

3.46 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

1.0

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)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

1H-1,2,4-triazol-1-ylacetic acid (Ref: CGA 142856)

Minor fraction

0.067

1H-1,2,4-triazol-3-ol (Ref: NOA 457654)

Minor fraction

2-amino-3-[1,2,4] triazol-1-yl-propionic acid (Ref: CGA 131013)

Minor fraction

triazole lactic acid

Minor fraction

triazole pyruvic acid

Minor fraction

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

Major fraction

0.170

triazole acetic acid (Ref: NOA 142856)

Minor fraction

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

5-(4-chlorophenyl)-5-hydroxy-4-methyl-6-(1H-1,2,4-triazol-1-yl)-2-hexanoic acid (Ref: NOA 405870)

M21/21a

Rat

5-(4-chloro-phenyl)-3,5-dihydroxy-4-methyl-6-[1,2,4]triazol-1-yl-hexanoic acid (Ref: NOA 405872)

M36(Z2)

Rat

1-[(E)-2-(4-chloro-phenyl)-3-cyclopropyl-but-1-enyl]-1H-[1,2,4]triazole (Ref: NOA 421155)

M38(Z1)

Ref: NOA 421152

Rat (Faeces)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

< 350

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

1.84

Mice

High

(ppm diet)

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

8.3

Unknown species Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

Colinus virginianus

High

Birds - Short term dietary (LC₅₀/LD₅₀)

> 146 mg kg⁻¹

Anas platyrhynchos

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

1.4

Anas platyrhynchos

High

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

168

Eisenia foetida corr

Moderate

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

0.75

Eisenia foetida as product corr

Moderate

Soil micro-organisms

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

Dose: 2.5 mg kg⁻¹ soil 35 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

55.8

Folsomia candida

Non-target plants

> 400

Beta vulgaris
Vegetative vigour, ER₅₀
as g ha⁻¹

> 400

Beta vulgaris
Seedling emeregnce, ER₅₀
as g ha⁻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)

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) as Mortality LR₅₀ g ha⁻¹

> 200

Chrysoperla carnea 1st instar

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹ 48 hr

< 80

Aphidius rhopalosiphi Adult

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

29.4

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)

19.0

Oncorhynchus mykiss

Moderate

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

0.65

Oncorhynchus mykiss

Moderate

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

> 20.58

Danio rerio Embryo

Moderate

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

> 22

Daphnia magna

Moderate

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

0.023

Daphnia magna

Moderate

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

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

8.3

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)

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

5.0

Chironomus riparius

Moderate

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

0.059

Lemna gibba

Moderate

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

0.099

Scenedesmus subspicatus

Moderate

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

0.021

Scenedesmus subspicatus

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)

< 350

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.47

Rat (nose only)

Other Mammal toxicity endpoints

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

0.02

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

0.02

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

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

0.02

Dermal penetration studies (%)

1-10

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Main route of exposure of bystanders is by spray drify but risk is considered low

Occupational

No unacceptable risks to operators or other workers identified

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

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 toxicant
Endocrine issues - Inhibition of aromatase activity, decrease of estrogens production
CLP data - limited evidence of carcinogenicity; US EPA - probable human carcinogen

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: H301, H373, H360D
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Stable under ambient conditions

TRANSLATIONS

Language

Name

English

cyproconazole

French

cyproconazole

German

Cyproconazol

Danish

cyproconazol

Italian

ciproconazolo

Spanish

ciproconazol

Greek

cyproconazole

Polish

cyprokonazol

Swedish

Hungarian

cyproconazole

Dutch

cyproconazool

Norwegian

Record last updated:	31/10/2024
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