Fenpropidin (Ref: CGA 114900)

Fenpropidin (Ref: CGA 114900)	Last updated: 17/07/2024
(Also known as: fenpropadine; Ro-123049/000)

SUMMARY

Fenpropidin is a cereal fungicide. It is highly soluble in water and highly volatile. It may be moderately persistent in soil systems and can also be persistent in water depending on local conditions. It is not expected to leach to groundwater. Whilst fenpropidin is highly toxic to algae, it is moderately toxic to most other organisms. It is also moderately toxic to mammals via the oral route. There is some evidence to suggest it may be carcinogenic but this is not a widespread conclusion.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: Potential for particle bound transport: High	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Mammals chronic toxicity: High

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. introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2029

GB LERAP status

Crop over 5m DRT - See Authorisation for Crop LERAP Details

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

15/05/2027

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
✓		✓	✓	✓	✓	✓	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Chemical structure

Isomerism

A chiral molecule; fenpropidin is a racemate

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 groups

Piperidine fungicide

Minimum active substance purity

960 g kg⁻¹ as racemate

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

614-049-6

CIPAC number

520

US EPA chemical code

012305

PubChem CID

91694

CLP index number

No data found

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 Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

Pale yellow viscous liquid

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

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

7.94 X 10⁰²

Calculated

Log P

2.9

at 25 °C

Moderate

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

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. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

3.39

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is potentially a concern for short and long range air transport

From soil surface

24 hr

Volatilisation is potentially a concern for short and long range air transport

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)

65.0

at 20 °C 99.5% purity

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

93.1

Moderately persistent

DT₅₀ (field)

49.2

Moderately persistent

DT₉₀ (lab at 20 °C)

478.4

Very persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2020 dossier lab studies DT₅₀ (normalised) range 10-551.4 days, DT₉₀ (measured) range 33.1-1832 days, Soils=14; field studies DT₅₀ range 7-116 days; Other studies: DT₅₀ lab 87-98 days, field 89-112 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) 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

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

632

Non-mobile

K_oc (mL g⁻¹)

71790

Notes and range

EU 2020 dossier K_f range 72-2431 mL g⁻¹, K_oc range 33210-317455 mL g⁻¹, Soils=5

Freundlich

K_f (mL g⁻¹)

172.3

Non-mobile

K_foc (mL g⁻¹)

18088

¹/_n

0.76

Notes and range

EU 2020 dossier K_f range 17.4-1644, K_foc range 953-210769 mL g⁻¹, ¹/_n 0.70=0.94, Soils=14

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.44

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

3.4

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

163

Danio rero

Threshold for concern

CT₅₀ (days)

0.7

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

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

2-methyl-2-(4-(2-methyl-3-piperidin-1-yl-propyl)-phenyl)-propionic acid (Ref: CGA 289267)

Major fractio

0.106

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

2-methyl-2-(4-(2-methyl-3-piperidin-1-yl-propyl)-phenyl)-propionic acid (Ref: CGA 289267)

Relevancy unknown

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

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

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

Colinus virginianus NOAEL

Moderate

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 500

Eisenia foetida corr

Moderate

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

Eisenia foetida 56 day corr

Moderate

Soil micro-organisms

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

Dose: 1.1 mg kg⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

93.0

Folsomia candida corr

Non-target plants

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)

Chronic

Notes

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds) as Mortality ER₅₀ range 750-1500 g ha⁻¹

1100

Coccinella septempunctata Larva

Beneficial insects (Lacewings) as Mortality ER₅₀ g ha⁻¹

> 750

Chrysoperla carnea Larva

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 750

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

< 400

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.93

Lepomis macrochirus

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.32

Salmo gairdneri

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

0.54

Daphnia magna

Moderate

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

0.54

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

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)

0.079

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.0057

Scenedesmus subspicatus 96 hr

High

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

> 0.001

Desmodesmus subspicatus

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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 (nose only)

Other Mammal toxicity endpoints

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

0.02

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

0.02

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

0.05

Rat SF=100

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

0.02

Dermal penetration studies (%)

1.1-18.0%

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

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapid elimination mainly via urine (77-86%) within 24 hr

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
US EPA - weak evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
May self-ignite at 265 DegC

CLP classification 2013

Health: H302, H317, H318, H332, H335, H373
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

fenpropidin

French

fenpropidine

German

Fenpropidin

Danish

fenpropidin

Italian

fenpropidin

Spanish

fenpropidin

Greek

Polish

fenpropidyna

Swedish

fenpropidin

Hungarian

Dutch

Norwegian

Record last updated:	17/07/2024
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