Cyprodinil (Ref: CGA 219417)

Cyprodinil (Ref: CGA 219417)	Last updated: 01/05/2020
(Not known by any other names)

SUMMARY

Cyprodinil is a systemic, broad-spectrum fungicide that has approval for use in the EU. It has a low solubility, is unlikely to leach to groundwater and is volatile. It soils it is moderately persistent in water systems its persistent depends upon local conditions and it is likely to degrade quickly in daylight. It is moderately toxic to mammals and their 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.

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

UK regulatory status

UK approval status

Approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Approved

Dossier rapporteur/co-rapporteur

France/Belgium

Date inclusion expires

30/04/2021

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

Listed in EU database

Yes

Approved for use (✓) or known to be used (#) in the following EU-27 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

Australia, USA

Chemical structure

Isomerism

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 group

Anilinopyrimidine

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

CIPAC number

511

US EPA chemical code

288202

PubChem CID

86367

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 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

Beige powder

Related substances & organisms

cyproconazole

fludioxonil

picoxystrobin

Formulations

Property

Value

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

Acanto Prima
Kayak
Switch
Unix

Example products using this active

DuPont
Syngenta
Ciba

UK LERAP status

Buffer probably required in UK - see product label

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)

Not expected to self ignite; Not highly flammable

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

1.00 X 10⁰⁴

Calculated

Log P

High

Bulk 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

Low volatility

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

6.60 X 10^-03

Non-volatile

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

Medium

Calculated

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 on plant matrix

Value

8.1

Note

Published literature RL₅₀ range 2.6-9.7 days, 6 field & undercover grown crops, various matrices, n=9; Grapes in cold storage RL₅₀=30 days.

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

21.27

Slightly mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.098

Minor fraction, Relevant

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

Soil

0.230

Major fraction, Relevant

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

Plant

Non relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

Soil

(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; Soil

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

Plant; Animal; Soil

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

Rat; Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

393

Whole fish

Threshold for concern

CT₅₀ (days)

0.5

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

High

(ppm diet)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

2.41

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.083

Oncorhynchus mykiss

Moderate

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

0.22

Daphnia magna

Moderate

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

0.0088

Daphnia magna

High

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

Non-target plants

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

2.6

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)

> 784

Low

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

112.5

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)

192

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

1470

48 hour
Aphidius rhopalosiphi adult

% Effect

Mortality [Dose: 0.75 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

2250

7 day
Typhlodromus pyri protonymph

% Effect

Mortality [Dose: 0.75 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 26.7 mg kg⁻¹ soil

Mesocosm study data

NOEAEC mg l⁻¹

0.013

Aquatic community

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)

> 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

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

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Code is usually 9

CLP classification 2013

Health: H317
Environment: H400, H410

EC Risk Classification

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

EC Safety Classification

S2, S24, S37, S46, S60, S61

WHO Classification

III (c) (Slightly hazardous / Company classification)

UN Number

Variable with product, usually 3077 or 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

cyprodinil

French

cyprodinil

German

Cyprodinil

Danish

cyprodinil

Italian

cyprodinil

Spanish

ciprodinil

Greek

Polish

cyprodynil

Swedish

cyprodinil

Hungarian

cyprodinil

Dutch

cyprodinil

Record last updated:	01/05/2020
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