cyprodinil (Ref: CGA 219417) |
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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
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:
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
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 | - | ![]() |
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:
ENVIRONMENTAL FATE
for cyprodinil
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 |
(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 | - | - |
HUMAN HEALTH AND PROTECTION
for cyprodinil
General:
Property ![]() |
Value | Source/Quality Score/Other Information ![]() |
Interpretation ![]() |
|
Threshold of Toxicological Concern (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 | ||||
- |
|
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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:
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
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