Cyprodinil (Ref: CGA 219417)

Cyprodinil (Ref: CGA 219417)	Last updated: 21/08/2024
(Not known by any other names)

SUMMARY

Cyprodinil is a systemic, broad-spectrum fungicide. It has a low solubility, is unlikely to leach to groundwater and is volatile. In soils it is moderately persistent but may be persistent in water systems depending on local conditions. It is moderately toxic to mammals and there is some concern that it may bioaccumulate. Whilst it is a recognised irritant no serious human health concerns have been identified. It is moderately toxic to birds, most aquatic organisms and earthworms. It is not considered toxic to 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: Potential for particle bound transport: High	Ecotoxicity High alert: Daphnia chronic ecotoxicity: High	Human health Moderate alert: Mammals chronic toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A broad spectrum foliar fungicide used to control a range of pathogens mainly on fruit

Example pests controlled

Grey mould; Scab; Powdery mildew; Botrytis; Eyespot

Example applications

Fruit including grapes, apples, pears, plums, strawberries; Almonds; Ornamentals; Cereals

Efficacy & activity

Wheat/Eyespot=High; Wheat/Mildew=Low; Barley/Rhynchosporium=Low; Barley/Net blotch=Low; Barley/Ramularia=Low

Availability status

Current

Introduction & key dates

1994, first reported & marketed

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2028

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France/Belgium

Date EC 1107/2009 inclusion expires

15/03/2025

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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, USA, Iran, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₄H₁₅N₃

Canonical SMILES

CC1=NC(=NC(=C1)C2CC2)NC3=CC=CC=C3

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

HAORKNGNJCEJBX-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H15N3/c1-10-9-13(11-7-8-11)17-14(15-10)16-12-5-3-2-4-6-12/h2-6,9,11H,7-8H2,1H3,(H,15,16,17)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
cyprodinil	-

General status

Pesticide type

Fungicide

Substance groups

Anilinopyrimidine fungicide; Aminopyrimidine fungicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic, absorbed through foliage. Inhibits protein synthesis.

CAS RN

121552-61-2

EC number

601-785-8

CIPAC number

511

US EPA chemical code

288202

PubChem CID

86367

CLP index number

612-242-00-X

Molecular mass

225.29

PIN (Preferred Identification Name)

4-cyclopropyl-6-methyl-N-phenylpyrimidin-2-amine

IUPAC name

4-cyclopropyl-6-methyl-N-phenylpyrimidin-2-amine

CAS name

4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidinamine

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

Beige powder

Formulations

Property

Value

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

DuPont
Syngenta
Ciba

Example products using this active

Acanto Prima
Kayak
Switch
Unix

Formulation and application details

Often supplied as an emulsifiable concentrate or wettable granules which 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)

Low

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

500000

Acetone

440000

Toluene

500000

Dichloromethane

26000

n-Hexane

Melting point (°C)

75.9

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

1.00 X 10⁰⁴

Calculated

Log P

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.21

Dissociation constant pKa) at 25 °C

4.44

Weak base

Vapour pressure at 20 °C (mPa)

5.10 X 10^-01

at 25°C

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

6.60 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Volatilisation is potentially a concern for short and long range air transport

From soil surface

Negligible

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

Neutral solution: 270.8nm = 29200
Acidic solution: 271.6nm = 23400, 316.8nm = 5700
Basic solution: 270.8nm = 28400

Surface tension (mN m⁻¹)

57.7 - 62.6

at 20°C

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)

Moderately persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

120

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 31-41 days, DT₉₀ range 103-135 days, field studies DT₅₀ range 11-98 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

8.3

Note

Published literature RL₅₀ range 2.6-25.0 days, 7 field & undercover grown crops, various matrices, n=10; Grapes in cold storage RL₅₀=30 days.

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

8.0

Note

Published literature RL₅₀ range 2.3-16.7 days, 5 field & undercover grown crops, various matrices, n=9; Peppers in cold storage RL₅₀=49 days.

Aqueous photolysis DT₅₀ (days) at pH 7

Value

13.5

Moderately fast

Note

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

Value

Stable

Note

Stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

142

Slow

Water phase only DT₅₀ (days)

12.5

Moderately fast

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

[Lettuce: 9.6 days @ 4 DegC, dark; Field study], [Table grapes: 29.8 days @ 4 DegC, dark; Field study], [White grape juice: 44 days @ 40 DegC; Lab study]

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)

21.27

Slightly mobile

K_foc (mL g⁻¹)

2277

¹/_n

0.888

Notes and range

EU dossier kf range 12.3-355.55, K_foc range 1618-4393 mL g⁻¹, ¹/_n range 0.839-0.931, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.06

Calculated

Low leachability

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

Value

2.17 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

0.5

Calculated using the Atkinson method, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

393

Whole fish

Threshold for concern

CT₅₀ (days)

0.5

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

4-cyclopropyl-6-methyl-pyrimidine-2-ylamine (Ref: CGA 249287)

Minor fraction

0.098

3-(4-cyclopropyl-6-methylpyrimidin-2-ylamino)phenol (Ref: CGA 275535)

Major fraction

0.230

4-cyclopropyl-6-methyl-2-phenylamino-pyrimidin-5-ol (Ref: CGA 304076)

Minor fraction

4-(4-cyclopropyl-6-methyl-pyrimidin-2-yl-amino)-phenol (Ref: CGA 304075)

Minor fraction

4-cyclopropyl-6-methyl-pyrimidin-2-ol (Ref: CGA 321915)

Minor fraction

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

(2-amino-6-cyclopropyl-pyrimidin-4-yl)-methanol (Ref: NOA 422054)
Note: LD50 rat > 2000 mg/kg bw

Plant; Animal

4-(4-cyclopropyl-6-methyl-pyrimidin-2-yl-amino)-phenol (Ref: CGA 304075)

Plant; Animal

4-cyclopropyl-6-methyl-pyrimidin-2-ol (Ref: CGA 321915)
Note: LD50 rat > 2000 mg/kg bw

Plant; Animal

6-cyclopropyl-2-phenylamino-pyrimidin-4-yl)-methanol (Ref: CGA 232449)

Rat; Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

High

(ppm diet)

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

72.7

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 500

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1534 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

Colinus virginianus NOEL

Moderate

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

192

Eisenia foetida

Moderate

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

Soil micro-organisms

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

Dose: 26.7 mg kg⁻¹ soil

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)

> 75

Apis mellifera

Moderate

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

112.5

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) as % Mortality at dose 0.75 kg ha⁻¹

30.7

Coccinella septempunctata

Beneficial insects (Lacewings)

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

1470

Aphidius rhopalosiphi Adult

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

2250

Typhlodromus pyri Protonymph

Beneficial insects (Ground beetles) as % Mortality at dose 0.75 kg ha⁻¹

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

2.41

Oncorhynchus mykiss

Moderate

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

0.083

Oncorhynchus mykiss

Moderate

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

5.07

Danio rerio Embryo

Moderate

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

0.22

Daphnia magna

Moderate

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

0.0088

Daphnia magna

High

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)

0.24

Chironomus riparius

Moderate

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

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

7.71

Lemna gibba

Moderate

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

2.6

Pseudokirchneriella subcapitata

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

0.013

Aquatic community

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.2

Rat

Other Mammal toxicity endpoints

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

0.03

Rat SF=100

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

None allocated

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

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

0.03

Rat SF=100

Dermal penetration studies (%)

0.5-6.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL's amended for berries July 2023

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

; ; ; ;

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

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317
Environment: H400, H410

WHO Classification

III (c) (Slightly hazardous / Company classification)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

cyprodinil

French

cyprodinil

German

Cyprodinil

Danish

cyprodinil

Italian

cyprodinil

Spanish

ciprodinil

Greek

Polish

cyprodynil

Swedish

cyprodinil

Hungarian

cyprodinil

Dutch

cyprodinil

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