cyprodinil (Ref: CGA 219417) ** Translations

Environmental Fate - Ecotoxicology - Human Health

GENERAL INFORMATION

Description: A broad spectrum fungicide used to control a range of pathogens including Tapesia yallundae, Botrytis spp., Alternaria spp. and Rhynchospium secalis

Introduction: 1994, first reported & marketed

EC Directive 1107/2009 (repealing 91/414):

Status	Annex 1
Dossier rapporteur/co-rapporteur	France
Date inclusion expires	30/04/2017

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia, USA

General status:

Pesticide type	Fungicide
Substance group	Anilinopyrimidine
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
Chemical formula	C14H15N3
SMILES	n1c(cc(nc1Nc2ccccc2)C3CC3)C
International Chemical Identifier (InChI)	InChI=1/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
Molecular mass (g mol-1)	225.29
IUPAC Name	4-cyclopropyl-6-methyl-N-phenylpyrimidin-2-amine
CAS Name	4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidinamine
Other status information	-
Herbicide Resistance Classification (HRAC)	Not applicable
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	9
Physical state	Beige powder
Related substances & organisms	cyproconazole fludioxonil picoxystrobin

Formulations:

Property	Value
Example manufacturers of products using this active	DuPont Syngenta
Example products using this active	Acanto Prima Kayak Switch Unix
UK LERAP status	LERAP Category B
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/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 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 25oC (mPa)		5.10 X 10-01	B5	Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1)		6.60 X 10-03	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		2.46 X 10-06	Q2	Moderately volatile
GUS leaching potential index		1.01	Calculated	Low leachability
SCI-GROW groundwater index (µg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.99 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
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)	-	-	-
	Note	EU dossier lab studies DT50 range 31-41 days, DT90 range 103-135 days, field studies DT50 range 11-98 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	Very persistent
	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	91/414 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

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	393	A5 Whole fish	Threshold for concern
	CT50 (days)	0.5		-
Bioaccumulation potential		-	Calculated	Moderate
Mammals - Acute oral LD50 (mg kg-1)		> 2000	B5 Rat	Moderate
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	-
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	-
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
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 - Acute 48 hour LD50 (µg bee-1)		113	A4 Oral	Low
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	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	14700	48 hour A5 Aphidius rhopalosiphi, adult	Harmless at 1 kg ha-1
	% Effect	46	Mortality Dose: 0.75 kg ha-1 A5 Aphidius rhopalosiphi, adult	Moderately harmful
Other arthropod (2)	LR50 g ha-1	2250	7 day A5 Typhlodromus pyri, protonymph	Harmless at 1 kg ha-1
	% Effect	10	Mortality Dose: 0.75 kg ha-1 A5 Typhlodromus pyri, protonymph	Harmless
Soil micro-organisms		Nitrogen mineralisation: No significant effect Carbon mineralisation: No significant effect	A5 Dose: 26.7 mg/kg soil	-
Mesocosm study data	NOEAEC mg l-1	0.013	A5 Aquatic community	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Mammals - Acute oral LD50 (mg kg-1)		> 2000	B5 Rat	Moderate
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	-
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 dependant	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	[No unacceptable risks to bystanders identified]
	Occupational	-
Examples of European MRLs (mg kg-1)	Value	Apples: 0.05; Wheat: 0.02
	Note	[A5 EU dossier proposals] For the EU pesticides database click here
Drinking Water MAC (µg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
	-	-
General human health issues		[Skin sensitiser]

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

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		[Not explosive], [IMDG Transport Code is usually 9]
EC Risk Classification		[Xi - Irritant: 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		[Usually Packaging Group III (minor danger)]

TRANSLATIONS