Valifenalate (Ref: IR5885)

Valifenalate (Ref: IR5885)	Last updated: 18/03/2024
(Also known as: valiphenal)

SUMMARY

Valifenalate is a fungicide used to control various infections in grapes and other crops. It has a low aqueous solubility but is soluble in most organic solvents. It is not considered to be volatile and is not persistent in soil systems but may be in water-sediment systems depending on local conditions. Based on its physicochemical properties valifenalate is not expected to leach to groundwater. Toxicity to biodiversity is relatively low. Valifenalate has a low oral toxicity but there is some evidence that it may be carcinogenic.

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: Drainflow: Slightly mobile	Ecotoxicity Moderate alert: Daphnia chronic ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

An anti-peronosporic fungicide that controls various types of fungal infections in many crops, including grapes

Example pests controlled

Downy mildew; Crown rot; Late blight

Example applications

Grapes; Tomatoes; Potatoes; Tobacco; Some vegetables; Lettuce

Efficacy & activity

Availability status

Current

Introduction & key dates

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/09/2029

GB LERAP status

Crop 5m - See Authorisation for Crop LERAP Details

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Hungary/Slovenia

Date EC 1107/2009 inclusion expires

30/09/2024

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

USA

Chemical structure

Isomerism

Valifenalate is a diastereoisomeric mixture of (R)- and (S)-valifenalate.

Chemical formula

C₁₉H₂₇ClN₂O₅

Canonical SMILES

CC(C)C(C(=O)NC(CC(=O)OC)C1=CC=C(C=C1)Cl)NC(=O)OC(C)C

Isomeric SMILES

CC(C)[C@@H](C(=O)NC(CC(=O)OC)C1=CC=C(C=C1)Cl)NC(=O)OC(C)C

International Chemical Identifier key (InChIKey)

DBXFMOWZRXXBRN-LWKPJOBUSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H27ClN2O5/c1-11(2)17(22-19(25)27-12(3)4)18(24)21-15(10-16(23)26-5)13-6-8-14(20)9-7-13/h6-9,11-12,15,17H,10H2,1-5H3,(H,21,24)(H,22,25)/t15?,17-/m0/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Acylamino acid fungicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Cellulose synthesis inhibitor. Absorbed and translocated throughout the plant

CAS RN

283159-90-0

EC number

608-192-3

CIPAC number

857

US EPA chemical code

PubChem CID

11338509

CLP index number

No data found

Molecular mass

398.89

PIN (Preferred Identification Name)

methyl N-(isopropoxycarbonyl)-L-valyl-(3RS)-3-(4-chlorophenyl)-β-alaninate

IUPAC name

methyl 3-(4-chlorophenyl)-3-[[(2S)-3-methyl-2-(propan-2-yloxycarbonylamino)butanoyl]amino]propanoate

CAS name

methyl N-[(1-methylethoxy)carbonyl]-L-valyl-3-(4-chlorophenyl)-β-alaninate

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

None identified

Physical state

White fine opaque powder when pure (>99.6%)

Formulations

Property

Value

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

Isagrow USA

Example products using this active

Java F
Compass

Formulation and application details

Usually supplied as water dispersible granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

24.1

Low

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

25.5

n-Heptane

29300

Acetone

25400

Ethyl Acetate

28800

Methanol

Melting point (°C)

147

Boiling point (°C)

367

Degradation point (°C)

367

Flashpoint (°C)

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

1.29 X 10⁰³

Calculated

Log P

3.11

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.25

Dissociation constant pKa) at 25 °C

-1.78

Vapour pressure at 20 °C (mPa)

9.6 X 10^-05

Low volatility

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

1.6 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

<240nm=221nn
No absorption >=290nm

Surface tension (mN m⁻¹)

66.0

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.15

Non-persistent

DT₅₀ (lab at 20 °C)

0.15

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

0.61

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2013 dossier lab studies DT₅₀ (normalised) range 0.6-0.37 days, DT₉₀ (measured) range 0.19-1.22 days, Soils=4

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) 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

7.62

Non-persistent

Note

pH4: stable at 55 °C, pH9: 0.33 days at 50 °C

Water-sediment DT₅₀ (days)

4.6

Fast

Water phase only DT₅₀ (days)

1000

Stable

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)

Slightly mobile

K_oc (mL g⁻¹)

753

Notes and range

EU dossier kd range 8-54 mL g⁻¹, K_oc range 375-1686 mL g⁻¹, soils=5

Freundlich

K_f (mL g⁻¹)

23.2

Slightly mobile

K_foc (mL g⁻¹)

735

¹/_n

0.961

Notes and range

EU dossier K_f range 7-73 mL g⁻¹, K_foc range 381-2135 mL g⁻¹, ¹/_n range 0.905-1.017, soils=5

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.93

Calculated

Low leachability

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

Value

8.04 X 10^-06

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

7.5

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

RS-beta-alanine, N-((1-methylethoxy)carbonyl)-L-valyl-3-(4-chlorophenyl)acid) (Ref: IR5839)

Major fraction

0.753

4-chlorobenzoic acid

Major fraction

0.502

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

(N-((1-methylethoxy)carbonyl)-L-valyl-3-(4-chlorophenyl)

Animal

3-amino-3-(4-chlorophenyl) propionic acid

Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

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)

> 2250

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5260 ppm

Anas platyrhynchos

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

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

> 1000

Eisenia foetida

Low

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

Soil micro-organisms

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

Dose: 26.67 mg kg⁻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)

> 106.6

Apis mellifera

Low

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

Chronic

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

> 9000

Aphidius rhopalosiphi

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

> 6400

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)

> 100

Oncorhynchus mykiss

Low

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

100

Oncorhynchus mykiss

Low

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

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

> 100

Daphnia magna

Low

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

3.2

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)

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)

> 100

Scenedesmus subspicatus

Low

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.12

Rat

Other Mammal toxicity endpoints

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

0.07

Dog SF=100

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

None allocated

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

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

0.07

Dog SF=100

Dermal penetration studies (%)

4.0-20.0%

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No chronic consumer intake concerns have been identified

Occupational

Acceptable for proposed uses

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 and extensive excretion mainly via bile (48-65%), urine (12-31%) and faeces (15-17%)

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

Possible liver, kidney and thyroid toxicant
CLP data - suspected of causing cancer

Handling issues

Property

Value and interpretation

General

Not oxidising, explosive or shock
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H351
Environment: H411

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

valifenalate

French

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	18/03/2024
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