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
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

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
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	cyproconazole fludioxonil picoxystrobin

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
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		Value	Source/Quality Score/Other Information	Interpretation
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		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	Value	2.33 X 10-02	Calculated	-
	Note	-
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		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
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
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	-	-

ECOTOXICOLOGY
for cyprodinil

Property		Value	Source/Quality Score/Other Information	Interpretation
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		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
				-
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		Value	Source/Quality Score/Other Information	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 - 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		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

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Record last updated: Tuesday 30 October 2018
Contact: aeru@herts.ac.uk
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