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cyprodinil (Ref: CGA 219417)
** Translations

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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 Click here for an explantaion of the general chemical status information
for cyprodinil

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

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur France/Belgium
Date inclusion expires 30/04/2019
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 European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
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)
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Anilinopyrimidine
Minimum active substance purity 980 g/kg
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 (g mol-1) 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) 9
Examples of recorded resistance -
Physical state Beige powder
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site 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
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

for cyprodinil

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 13 B5 Low
Solubility - In organic solvents at 20oC (mg l-1) 500000 A5 - Acetone -
440000 A5 - Toluene -
500000 A5 - Dichloromethane -
26000 A5 - n-Hexane -
Melting point (oC) 75.9 A5 -
Boiling point (oC) - - -
Degradation point (oC) - - -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 1.00 X 1004 Calculated -
Log P 4 B5 High
Bulk density (g ml-1)/Specific gravity 1.21 A5 -
Dissociation constant (pKa) at 25oC 4.44 B5 -
Note: Weak base
Vapour pressure at 20oC (mPa) 5.10 X 10-01 B5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 6.60 X 10-03 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.11 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 2.33 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
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 A5 -
Surface tension (mN m-1) 57.7 - 62.6 A5 at 20oC -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 37 A5 Moderately persistent
DT50 (lab at 20oC) 53 A5 Moderately persistent
DT50 (field) 45 A5 Moderately persistent
DT90 (lab at 20oC) 120 A5 -
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 R4 -
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 R4 -
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 A5 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 4 to pH 9
Water-sediment DT50 (days) 142 A5 Slow
Water phase only DT50 (days) 12.5 A5 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 21.27 A5 Slightly mobile
Kfoc 2277
1/n 0.888
Notes and range EU dossier kf range 12.3-355.55, Kfoc range 1618-4393 mL/g, 1/n range 0.839-0.931, Soils=5
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 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) This metabolite may cause environmental pollution, click here for further information 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
(6-cyclopropyl-2-phenylamino-pyrimidin-4-yl)-methanol
(Ref: CGA 232449)
- Rat; Plant - -
4-(4-cyclopropyl-6-methyl-pyrimidin-2-yl-amino)-phenol
(Ref: CGA 304075)
- Plant; Animal; Soil - -
4-cyclopropyl-6-methyl-2-phenylamino-pyrimidin-5-ol
(Ref: CGA 304076)
- Soil - -
4-cyclopropyl-6-methyl-pyrimidin-2-ol
(Ref: CGA 321915)
Note: LD50 rat > 2000 mg kg-1 bw
- Plant; Animal; Soil - -
(2-amino-6-cyclopropyl-pyrimidin-4-yl)-methanol
(Ref: NOA 422054)
Note: LD50 rat > 2000 mg kg-1 bw
- Plant; Animal - -


ECOTOXICOLOGY

for cyprodinil

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 393 A5 Whole fish Threshold for concern
CT50 (days) 0.5 -
Mammals - Acute oral LD50 (mg kg-1) > 2000 B5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 3 L2 Rat, 2 year High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 500 A5 Anas platyrhynchos Moderate
Birds - Short term dietary (LC50/LD50) > 1534 mg kg bw-1 day-1 A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 2.41 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.083 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.22 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.0088 A5 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 A5 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 A5 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 2.6 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 784 A5 Low
Oral acute 48 hour LD50 (μg bee-1) 112.5 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 192 B5 Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 1470 48 hour
A5 Aphidius rhopalosiphi, adult
-
% Effect 46 Mortality
Dose: 0.75 kg ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 2250 7 day
A5 Typhlodromus pyri, protonymph
-
% Effect 10 Mortality
Dose: 0.75 kg ha-1
A5 Typhlodromus pyri, protonymph
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 26.7 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 0.013 A5 Aquatic community -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for cyprodinil

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 2000 B5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 1.2 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.03 A5 Rat, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) None allocated A5 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.03 A5 Rat, SF=100 -
Dermal penetration studies (%) 0.5-6.0 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public No unacceptable risks to bystanders identified
Occupational -
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

General human health issues No further information available

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive
IMDG Transport Code is usually 9
CLP classification 2013 Health: H317
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R43
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S24, S37, S46, S60, S61
WHO Classification III - company classification - Slightly hazardous
US EPA Classification (formulation) III, IV - Caution - Slightly toxic, Caution - Not acutely toxic
UN Number Variable with product, usually 3077 or 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for cyprodinil

Language Name
English cyprodinil
French cyprodinil
German Cyprodinil
Danish cyprodinil
Italian cyprodinil
Spanish ciprodinil
Greek -
Slovenian ciprodinil
Polish cyprodynil
Swedish cyprodinil
Hungarian cyprodinil
Dutch cyprodinil

Record last updated: Tuesday 30 October 2018
Contact: aeru@herts.ac.uk
© University of Hertfordshire