Fenpropidin (Ref: CGA 114900)

Fenpropidin (Ref: CGA 114900)	Last updated: 19/01/2021
(Also known as: fenpropadine; Ro-123049/000)

GENERAL INFORMATION

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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Czech Republic/Germany

Date EC 1107/2009 inclusion expires

31/12/2021

EU Candidate for substitution (CfS)

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

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⁻¹

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

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)

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

Alpha Fenpropidin
Instinct
Spyrale
Tern

Example products using this active

Headland
Makhteshim-Agan
Syngenta

Formulation and application details

Often supplied as an emulsifiable concentrate that is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

530

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

250000

Heptane

250000

Xylene

250000

Acetone

250000

Ethyl acetate

Melting point (°C)

-64.6

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

243

Flashpoint (°C)

156

Octanol-water partition coefficient at pH 7, 20 °C

3.98 X 10⁰²

Calculated

Log P

2.6

Low

Bulk density (g ml⁻¹)

0.91

Dissociation constant pKa) at 25 °C

10.13

Very weak acid

Vapour pressure at 20 °C (mPa)

17.0

Highly volatile

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

10.7

Moderately volatile

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

Surface tension (mN m⁻¹)

51.6-52.1

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

109

Persistent

DT₅₀ (field)

49.2

Moderately persistent

DT₉₀ (lab at 20 °C)

289

Persistent

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

3.2

Note

Wheat straw, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Insignificant route of degradation

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable pH 3 to pH 9 at 50 °C

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

1.8

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

51.1

Slightly mobile

K_foc

3808

¹/_n

0.71

Notes and range

EU dossier K_f range 17.4-117.1, K_foc range 2105-5194 mL g⁻¹, ¹/_n 0.56-0.80, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.71

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

1.35 X 10^-02

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

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)

1-[3-(4-tert-butyl-phenyl)-2-methyl-propyl]-piperidine-1-oxide (Ref: CGA 289263)

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

163

Threshold for concern

CT₅₀ (days)

0.7

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1452

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Unknown species Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

1899

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1417 mg kg bw⁻¹ day⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

14.6

Colinius virginianus NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.9

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.32

Salmo gairdneri

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.54

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.32

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

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

40.0

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

Scenedemus subspicatus 96 hour

High

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

0.0014

Unknown species

Moderate

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

46.0

Apis mellifera

Moderate

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 10

Apis mellifera

Moderate

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)

> 500

Eisenia foetida corr

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Eisenia foetida 56 days corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

93.0

Folsomia candida 28d corr

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Harmless

Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

750

Aphidius rhopalosiphi

% Effect

100

Mortality [Dose: 750 g ha⁻¹]
Aphidius rhopalosiphi

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 1.1 mg kg⁻¹ 28 days

Mesocosm study data

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)

1452

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

4000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.22

Rat 4 hr

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.02

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.02

Dog SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.02

Dog SF=100

Dermal penetration studies (%)

2.5-6.4

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk to bystanders

Occupational

Possible risk to operators and other farm workers - PPE advised

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Harmful by inhalation, in contact with skin and if swallowed
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and 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)

UN Number

Variable with product, usually 2902 or 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fenpropidin

French

fenpropidine

German

Fenpropidin

Danish

fenpropidin

Italian

fenpropidin

Spanish

fenpropidin

Greek

Polish

fenpropidyna

Swedish

fenpropidin

Hungarian

Dutch

Record last updated:	19/01/2021
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