fenpropidin (Ref: CGA 114900) ** fenpropadine ** Ro-123049/000 ** Translations

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GENERAL INFORMATION
for fenpropidin

Description: A piperidine contact fungicide used to control a range of diseases in cereals

Example pests controlled: Powdery mildew, Rhynchosporium, Brown and yellow rusts, Leaf spots

Example applications: Cereals including wheat and barley

Efficacy & activity: Wheat/Mildew=Moderate; Wheat/Septoria=Low; Wheat/Rust=Low; Barley/Rhynchosporium=Low; Barley/Mildew=Low; Barley/Rust=Low; Barley/Net blotch=Low

Availability status: Current

Introduction & key dates: 1986

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

Status	Approved
Dossier rapporteur/co-rapporteur	Czech Republic/Germany
Date inclusion expires	31/12/2018
EU Candidate for substitution (CfS)	No
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

Chemical structure:

Isomerism	A chiral molecule, fenpropidin is an isomeric mixture.
Chemical formula	C19H31N
Canonical SMILES	CC(CC1=CC=C(C=C1)C(C)(C)C)CN2CCCCC2
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	MGNFYQILYYYUBS-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C19H31N/c1-16(15-20-12-6-5-7-13-20)14-17-8-10-18(11-9-17)19(2,3)4/h8-11,16H,5-7,12-15H2,1-4H3
2D structure diagram/image available?	Yes

General status:

Pesticide type	Fungicide
Substance group	Unclassified
Minimum active substance purity	960 g/kg
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Systemic with curative and protective action. Inhibits sterol biosynthesis in membranes.
CAS RN	67306-00-7
EC number	-
CIPAC number	520
US EPA chemical code	012305
PubChem CID	91694
Molecular mass (g mol-1)	273.46
PIN (Preferred Identification Name)	rac-1-[(2R)-3-(4-tert-butylphenyl)-2-methylpropyl]piperidine
IUPAC name	1-[(RS)-3-(4-tert-butylphenyl)-2-methylpropyl]piperidine
CAS name	1-(3-(4-(1,1-dimethylethyl)phenyl)-2-methylpropyl)piperidine
Other status information	PAN listed Highly Hazardous Chemical
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)	5
Examples of recorded resistance	-
Physical state	Pale yellow viscous liquid
Related substances & organisms	difenoconazole

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Headland Makhteshim-Agan Syngenta
Example products using this active	Alpha Fenpropidin Instinct Spyrale Tern
UK LERAP status	None
Formulation and application details	Often supplied as an emulsifiable concentrate that is mixed with water and applied as a spray.

ENVIRONMENTAL FATE
for fenpropidin

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		530	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		250000	A5 - Heptane	-
		250000	A5 - Xylene	-
		250000	A5 - Acetone	-
		250000	A5 - Ethyl acetate	-
Melting point (oC)		-64.6	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		243	A5	-
Flashpoint (oC)		156	L3	-
Octanol-water partition coefficient at pH 7, 20oC	P	3.98 X 1002	Calculated	-
	Log P	2.6	B5	Low
Bulk density (g ml-1)/Specific gravity		0.91	L3	-
Dissociation constant (pKa) at 25oC		10.13	A5	-
		Note: Very weak acid
Vapour pressure at 20oC (mPa)		17.0	A5	Highly volatile
Henry's law constant at 25oC (Pa m3 mol-1)		10.7	A5	Moderately volatile
GUS leaching potential index		0.85	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.68 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	High
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: Maxima at 218.2 & 263.7nm; [Acidic solution: Maxima at 217.9 & 262.9nm; [Basic solution: Maxima at 219.2 & 263.9; [No absorbance maxima >290nm	A5	-
Surface tension (mN m-1)		51.6-52.1	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		R3
Soil degradation (days) (aerobic)	DT50 (typical)	90	B4	Moderately persistent
	DT50 (lab at 20oC)	109	A5	Persistent
	DT50 (field)	49.2	A5	Moderately persistent
	DT90 (lab at 20oC)	289	A5	-
	DT90 (field)	-	-	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier lab studies DT50 range 58-217 days, DT90 range 192-365 days, field studies DT50 range 7-116 days; Other studies: DT50 lab 87-98 days, field 89-112 days
Dissipation rate RL50 on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL50 on and in plant matrix	Value	-	Wh - at straw, n=1	-
	Note	3.2
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	-
	Note	Insignificant route of degradation
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 3 to pH 9 at 50 degC
Water-sediment DT50 (days)		34	A5	Moderately fast
Water phase only DT50 (days)		1.8	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	51.1	A5	Slightly mobile
	Kfoc	3808
	1/n	0.71
	Notes and range	EU dossier Kf range 17.4-117.1, Kfoc range 2105-5194 mL/g, 1/n 0.56-0.80, Soils=6
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
2-methyl-2-(4-(2-methyl-3-piperidin-1-yl-propyl)-phenyl)-propionic acid (Ref: CGA 289267)		Soil	0.106	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
1-[3-(4-tert-butyl-phenyl)-2-methyl-propyl]-piperidine-1-oxide (Ref: CGA 289263)	-	Soil	-	-
2-methyl-2-[4-(2-methyl-3-piperidin-1-yl-propyl)-phenyl]-propan-1-ol (Ref: CGA 289268)	-	a = Rat (Faeces, Bile); b= Animal	a=0.270	-
3-hydroxy-2-methyl-2-[4-(2-methyl-3-piperidin-1-yl-propyl)-phenyl]-propionic acid (Ref: SYN 515213)	-	Animal (Tissue)	-	-

ECOTOXICOLOGY
for fenpropidin

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	163	A5	Threshold for concern
	CT50 (days)	0.7		-
Mammals - Acute oral LD50 (mg kg-1)		1452	A5 Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg-1)	20	B5 Rat	High
	(ppm diet)	60		-
Birds - Acute LD50 (mg kg-1)		1899	A5 Anas platyrhynchos	Moderate
Birds - Short term dietary (LC50/LD50)		> 1417 mg kg bw-1 day-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		1.9	A5 Lepomis macrochirus	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		0.32	A5 Salmo gairdneri	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.54	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.32	A5 Daphnia magna	Moderate
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)		1.0	A5 Chironomus riparius	Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		40.0	A5 Chironomus riparius	Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.0057	A5 Scenedemus subspicatus, 96 hour	High
Algae - Chronic 96 hour NOEC, growth (mg l-1)		0.0014	Q2 Unknown species	Moderate
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	-	-	-
	Oral acute 48 hour LD50 (μg bee-1)	> 10	A5	Moderate
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 500	A4 Eisenia foetida	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		10	A5 Eisenia foetida, 56 days	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	93.0	A5 Folsomia candida, 28 day NOEC mg kg-1	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	Harmless	AA2 Typhlodromus pyri	-
Other arthropod (2)	LR50 g ha-1	750	A5 Aphidius rhopalosiphi	-
	% Effect	100	Mortality Dose: 750 g ha-1 A5 Aphidius rhopalosiphi	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 1.1 mg kg-1, 28 days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for fenpropidin

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)		1452	A5 Rat	Moderate
Mammals - Dermal LD50 (mg kg-1 body weight)		> 4000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		1.22	A5 Rat, 4 hr	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.02	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.02	A5 Dog, SF=100	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.02	A5 Dog, SF=100	-
Dermal penetration studies (%)		2.5-6.4	A5 concentration dependent	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Minimal risk to bystanders
	Occupational	Possible risk to operators and other farm workers - PPE advised
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		Harmful by inhalation, in contact with skin and if swallowed USEPA - some evidence to suggest possible human carcinogen

: 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 or oxidising IMDG Transport Code is variable depending upon product, often either 6.1 or 9
CLP classification 2013		Health: H302, H317, H318, H332, H335, H373 Environment: H400, H410
EC Risk Classification		Xn - Harmful: R20/22, R41, R43, R48/22 Xi - Irritant: R36/38
EC Safety Classification		-
WHO Classification		II	-	Moderately hazardous
US EPA Classification (formulation)		No consensus across products or no products available	-	-
UN Number		Variable with product, usually 2902 or 3082
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for fenpropidin

Language	Name
English	fenpropidin
French	fenpropidine
German	Fenpropidin
Danish	fenpropidin
Italian	fenpropidin
Spanish	fenpropidin
Greek	-
Slovenian	fenpropidin
Polish	fenpropidyna
Swedish	fenpropidin
Hungarian	-
Dutch	-

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Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk