Cyprofuram (Ref: SN 78314)	Last updated: 07/01/2021
(Also known as: stanza)

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GENERAL INFORMATION

Description	A largely obsolete fungicide that was formerly used on vines and potatoes to control Oomycetes
Example pests controlled	Downey mildew; Late blight
Example applications	Vines; Potatoes; Vegetables including broccoli, lettuce, curcubits, peas, onions; Some ornamentals; Cotton
Efficacy & activity	-
Availability status	Obsolete
Introduction & key dates	1982, first reported

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
UK LERAP status	No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Not approved
Dossier rapporteur/co-rapporteur	Not applicable
Date EC 1107/2009 inclusion expires	Expired
EU Candidate for substitution (CfS)	Not applicable
Listed in EU database	Yes
Approved for use (✓) under EC 1107/2009 in the following EU 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

Also used in	-

Chemical structure

Isomerism	Cyprofuram is a chiral molecule.
Chemical formula	C₁₄H₁₄ClNO₃
Canonical SMILES	C1CC1C(=O)N(C2CCOC2=O)C3=CC(=CC=C3)Cl
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	KRZUZYJEQBXUIN-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C14H14ClNO3/c15-10-2-1-3-11(8-10)16(13(17)9-4-5-9)12-6-7-19-14(12)18/h1-3,8-9,12H,4-7H2
2D structure diagram/image available?	Yes

General status

Pesticide type	Fungicide
Substance group	Anilide
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Systemic, inhibits zoospore release
CAS RN	69581-33-5
EC number	274-050-9
CIPAC number	556
US EPA chemical code	-
PubChem CID	50590
Molecular mass	279.72
PIN (Preferred Identification Name)	rac-N-(3-chlorophenyl)-N-[(3R)-2-oxooxolan-3-yl]cyclopropane-1-carboxamide
IUPAC name	(RS)-α-[N-(3-chlorophenyl)cyclopropanecarboxamido]-γ-butyrolactone
CAS name	N-(3-chlorophenyl)-N-(tetrahydro-2-oxo-3-furanyl)cyclopropanecarboxamide
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)	Not known
Examples of recorded resistance	-
Physical state	-

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Vinicur
Example products using this active	Schering
Formulation and application details	Usually formulated as a suspension concentrate or wettable powder

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		574	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source at 25 °C	High
Solubility - In organic solvents at 20 °C (mg l⁻¹)		500000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Acetone	-
		500000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Dichloromethane	-
		330000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Cyclohexanone	-
		50000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Ethanol	-
Melting point (°C)		95	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.45 X 1001	Calculated	-
	Log P	1.16	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source	Low
Bulk density (g ml⁻¹)		-	-	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		-	-	-
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		-	-	-
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		-	-	-
Surface tension (mN m⁻¹)		-	-	-

Degradation

Property		Value	Source; quality score; and other information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT₅₀ (typical)	-	-	-
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	-
Dissipation rate RL₅₀ on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	-	-	-
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	-	-	-
	Note	-
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		-	-	-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		-	-	-
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	Cannot be calculated	-	-
	Note	-
Potential for particle bound transport index		-	-	-
Potential for loss via drain flow		-	-	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	Low risk	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source Based on LogP < 3	Low risk
	CT₅₀ (days)	-		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		174	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	-	-
	(ppm diet)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		2000	V2 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 2 = Unverified data of unknown source Wild bird	Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		-	-	-
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
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)		-	-	-
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)		-	-	-
Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		-	-	-
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)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	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)		-	-	-
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	-	-	-
	% Effect	-	-	-
Other arthropod (2)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	-	-	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	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)		174	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Rat	Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		1000	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Rabbit	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		-	-	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		-	-	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		-	-	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)		-	-	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Routes	Public	-
	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 A0 A = Chromosome aberration (EFSA database) 0 = No data ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant No data found XNo, known not to cause a problem No data found Respiratory tract irritant Skin irritant Skin sensitiser No data found XNo, known not to cause a problem No data found Eye irritant Phototoxicant   ?Possibly, status not identified No data found
General human health issues		Toxic

Handling issues

Property	Value and interpretation
General	Not compatible with strong alkaline materials including Bordeaux mixture & lime sulphur
CLP classification 2013	Health: H301, H312 Environment: H400, H410
EC Risk Classification	T - Toxic: R25 Xn - Harmful: R21 N - Dangerous for the environment: R50, R53
EC Safety Classification	S1/2, S36/37, S60, S61
WHO Classification	II (Moderately hazardous)
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	cyprofuram
French	-
German	-
Danish	-
Italian	-
Spanish	-
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-

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Record last updated:	07/01/2021
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