Fenpropimorph (Ref: CGA 101031)

Fenpropimorph (Ref: CGA 101031)	Last updated: 23/10/2024
(Also known as: fenpropimorphe; BAS 421F)

SUMMARY

Fenpropimorph is a morpholine fungicide used to control various pathogens on a variety of crops including cereals. It has a low aqueous solubility and a low volatility. It is moderately persistent in soil systems but my ne more persistent in water systems depending on local conditions. Based on its physico-chemical properties it is not expected to leach to groundwater. Toxicity to biodiversity tends to be low to moderate. It is moderately toxic to humans via the oral route. No information on its potential to cause chronic health effects have been identified.

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 Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A fungicide used to control various fungal pathogens

Example pests controlled

Powdery mildew; Scald; Yellow & brown rusts; Mycosphaerella spp.

Example applications

Cereals including wheat, barley, oats, rye and tritical; Bananas and plantains

Efficacy & activity

Wheat/Mildew=Low; Wheat/Septoria=Low; Wheat/Rust=Moderate-low; Barley/Rhynchosporium=Low; Barley/Mildew=Low; Barley/Rust=Low; Barley/Ramularia=Low

Availability status

Current

Introduction & key dates

1983, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Latvia/Slovenia

Date EC 1107/2009 inclusion expires

Expired

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, fenpropimorph is an isomeric mixture where both enantiomers are similarly active

Chemical formula

C₂₀H₃₃NO

Canonical SMILES

CC1CN(CC(O1)C)CC(C)CC2=CC=C(C=C2)C(C)(C)C

Isomeric SMILES

C[C@@H]1CN(C[C@@H](O1)C)CC(C)CC2=CC=C(C=C2)C(C)(C)C

International Chemical Identifier key (InChIKey)

KXTJYESBRKJMKP-CPZRZBMISA-N

International Chemical Identifier (InChI)

InChI=1S/C20H33NO/c1-15(12-21-13-16(2)22-17(3)14-21)11-18-7-9-19(10-8-18)20(4,5)6/h7-10,15-17H,11-14H2,1-6H3/t15?,16-,17+

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide, Other substance

Other bioactivity & uses

Biocide, Anti-fouling substance, Slimicide, Wood preservative

Substance groups

Morpholine fungicide

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

Substance origin

Synthetic

Mode of action

Systemic with protective and curative action. Disrupts membrane function.

CAS RN

67564-91-4

EC number

266-719-9

CIPAC number

427

US EPA chemical code

121402

PubChem CID

93365

CLP index number

613-124-00-0

Molecular mass

303.48

PIN (Preferred Identification Name)

rac-(2R,6S)-4-[(2E)-3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine

IUPAC name

cis-4-[(RS)-3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine

CAS name

(2R,6S)-rel-4-(3-(4-(1,1-dimethylethyl)phenyl)-2-methylpropyl)-2,6-dimethylmorpholine

Other status information

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

Colourless oily liquid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

BASF
Dow AgroSciences
DuPont
Greencrop
Syngenta
Maag
May & Baker

Example products using this active

Amistar Pro
Corbel
Colstar
Jackdraw
Mantra
Orka
Pluton
Tango super
Volley 880L

Formulation and application details

Often supplied as an emulsifiable concentrate or suspension concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

4.32

Low

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

7604000

Acetone

7646000

Toluene

7780000

Ethyl acetate

7892000

Methanol

Melting point (°C)

-44

Boiling point (°C)

Degradation point (°C)

310

Flashpoint (°C)

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

3.16 X 10⁰⁴

Calculated

Log P

4.5

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

0.93

Dissociation constant pKa) at 25 °C

6.98

Weak acid

Vapour pressure at 20 °C (mPa)

3.5

Low volatility. 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)

2.74 X 10^-04

Non-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

203nm = 11000, 219nm = 11000, 242nm = 210, 464nm = 420, 270nm = 320, 272nm = 420, no absorption above 290nm

Surface tension (mN m⁻¹)

49.0

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)

19.6

Non-persistent

DT₅₀ (field)

25.5

Non-persistent

DT₉₀ (lab at 20 °C)

72.4

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 9.5-124 days, DT₉₀ range 49.5-411.2 days, field studies DT₅₀ 8.8-50.6 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

2.2

Note

Published literature RL₅₀ range 1.9-2.5 days, sugarbeet leaves, wind tunnel expt., n=2

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable pH 3 to pH 9 at 25 °C

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

2.65

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

44.2

Non-mobile

K_foc (mL g⁻¹)

4382

¹/_n

1.050

Notes and range

EU dossier K_f range 22.2-74.8 mL g⁻¹, K_foc range 2772-5943 mL g⁻¹, ¹/_n range 0.867-1.340, Soils=3

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.50

Calculated

Low leachability

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

Value

9.90 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

2.9

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

428

Mean of several studies

Threshold for concern

CT₅₀ (days)

3.8

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

fenpropimorph carboxylic acid (Ref: CGA 294975)

Minor fraction

0.080

cis-2,6-dimethylmorpholine

Minor fraction

0.090

4-[3-(4-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine-3-one (Ref: BF-421-15)

4-[3-(4-tert-butylphenyl)-2-methyl-1-oxopropyl]-cis-2,6-dimethylmorpholine (Ref: BF-421-13)

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

4-[3-(4-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine-3-one (Ref: BF-421-15)
Note: CAS no: 264957

Plan

3-[4-(1-carboxy-1-methylethyl)phenyl]-2-methylpropionic acid (Ref: BF-421-17)

Rat (Urine, Faceces)

Ref: BF-421-18

Animal

Ref: BF-421-19

Animal

Ref: BF-421-20

Plant

Ref: BF-421-21

Animal

Ref: BF-421-24

Animal

2-{4-[3-(2,6-dimethylmorpholin-4-yl)-2-methylpropyl]phenyl}-2-methylpropan-1-ol (Ref: BF-421-1)
Note: CAS no: 246719

Ro14-8156

Plant; Animal

BF-421-1-sulfate

Animal

BF-421-1-glucoside

Plant

BF-421-1-diglucoside

Plant

2-{4-[3-(2-hydroxymethyl-6-methylmorpholin-4-yl)-2-methylpropyl]phenyl}-2-methylpropionic acid (Ref: BF-421-3)

Ro15-6374

Rat (Urine, Faceces); Animal

2-{4-[3-(2-hydroxypropylamino)-2-methylpropyl]phenyl}-2-methylpropionic acid (Ref: BF-421-4)

Ro15-1289

Animal

[3-(4-tert-butylphenyl)-2-methylpropyl](2-hydroxypropyl)amine (Ref: BF-421-7)

Ro15-4422

Plant

2-methyl-2-(4-carboxyphenyl)propionic acid (Ref: BF-421-12)

Animal

4-[3-(4-tert-butylphenyl)-2-methyl-1-oxopropyl]-cis-2,6-dimethylmorpholine (Ref: BF-421-13)
Note: CAS no: 131051

Plant

4-(2-hydroxy-1,1-dimethylethyl)benzoic acid (Ref: BF-421-16)

Rat (Urine, Faceces); Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1670

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.3

Rat

High

(ppm diet)

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 881 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

> 30.3

Colinus virginianus NOEL

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

> 4.7

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 7.5 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

> 100

Apis mellifera

Low

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

> 95.6

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)

Beneficial insects (Lacewings)

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

25.7

Aphidius rhopalosiphi

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

468

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)

2.3

Lepomis macrochirus

Moderate

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

0.1

Oncorhynchus mykiss

Moderate

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

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

2.24

Daphnia magna

Moderate

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

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)

0.13

Chironomus riparius 20 day

Moderate

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

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

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

0.327

Pseudokirchneriella subcapitata

Moderate

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

0.058

Pseudokirchneriella subcapitata Growth

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)

1670

Rat

Moderate

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

4000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.9

Rat 4 hr

Other Mammal toxicity endpoints

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

0.003

Rat SF=100

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

0.03

Rat SF=500

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

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

None allocated

Dermal penetration studies (%)

10.0

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for registered uses

Occupational

PPE required

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

EU expected to amend MRL in early 2023

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H315, H361d
Environment: H411

WHO Classification

III (Slightly hazardous)

UN Number

UN3082

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

fenpropimorph

French

fenpropimorphe

German

Fenpropimorph

Danish

fenpropimorph

Italian

fenpropimorf

Spanish

fenpropimorf

Greek

fenpropimorph

Polish

fenpropimorf

Swedish

fenpropimorf

Hungarian

fenpropimorf

Dutch

fenpropimorf

Norwegian

Record last updated:	23/10/2024
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