Pyriofenone (Ref: IKF-309)

Pyriofenone (Ref: IKF-309)	Last updated: 26/08/2024
(Not known by any other names)

SUMMARY

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; 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; Daphnia chronic ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A preventative and curative fungicide for the control of powdery mildew

Example pests controlled

Powdery mildew

Example applications

Wheat; Barley; Grape vines; Curcubits

Efficacy & activity

Availability status

Current

Introduction & key dates

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2030

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Latvia/Germany

Date EC 1107/2009 inclusion expires

31/01/2025

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

None

Chemical formula

C₁₈H₂₀ClNO₅

Canonical SMILES

CC1=CC(=C(C(=C1C(=O)C2=C(C(=CN=C2OC)Cl)C)OC)OC)OC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

NMVCBWZLCXANER-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H20ClNO5/c1-9-7-12(22-3)16(23-4)17(24-5)13(9)15(21)14-10(2)11(19)8-20-18(14)25-6/h7-8H,1-6H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Aryl phenol ketone fungicide

Minimum active substance purity

965 g kg⁻¹

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

Inhibits the formation of appressoria and the subsequent penetration of the hyphae in the plant cells

CAS RN

688046-61-9

EC number

692-456-8

CIPAC number

827

US EPA chemical code

PubChem CID

23082663

CLP index number

No data found

Molecular mass

365.81

PIN (Preferred Identification Name)

(5-chloro-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone

IUPAC name

(5-chloro-2-methoxy-4-methyl-3-pyridyl)(4,5,6-trimethoxy-o-tolyl)methanone

CAS name

(5-chloro-2-methoxy-4-methyl-3-pyridinyl)(2,3,4-trimethoxy-6-methylphenyl)methanone

Other status information

Possible marine pollutant

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

White crystalline powder

Formulations

Property

Value

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

ISK Biosciences Europe NV
Belchim Crop Protection

Example products using this active

IKF-309 180SC
property

Formulation and application details

Usually formulated as a soluble concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.56

Low

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

9200

n-Heptane

250000

Xylene

250000

Acetone

17800

n-Octanol

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

100

Flashpoint (°C)

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

1.58 X 10⁰³

Calculated

Log P

3.2

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data - observations of feeding and metabolism studies

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0019

Low volatility

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

0.00019

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral: 298nm=495

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

72.6

Moderately persistent

DT₅₀ (lab at 20 °C)

72.6

Moderately persistent

DT₅₀ (field)

19.0

Non-persistent

DT₉₀ (lab at 20 °C)

355

Persistent

DT₉₀ (field)

1330

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 50.9-189 days DT₉₀ range 160-787 days, Field data DT₅₀ 10.5-32.8 days, DT₉₀ 413-2415 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.6

Note

Oriental melon fruit, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.1

Purified water

Moderately fast

Note

33 days in natural water

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

Value

Stable

Note

Stable pH4 to pH9

Water-sediment DT₅₀ (days)

8.4

Fast

Water 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)

21.9

Slightly mobile

K_foc (mL g⁻¹)

1485

¹/_n

0.91

Notes and range

EU dossier K_f range 12.9-13.6 mL g⁻¹, K_foc range 705-2720 mL g⁻¹, ¹/_n range 0.86-0.98, Soils=5

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.06

Calculated

Low leachability

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

Value

1.94 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

0.63

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)

160

Threshold for concern

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

(5-chloro-2-methoxy-4-methyl-3-pyridinyl)(3,4-dihydroxy-2-methoxy-6-methylphenyl)methanone (Ref: 2MDPM)

Major fraction

0.225

Anaerobic

(5-chloro-2-methoxy-4-methyl-3-pyridinyl)(3-hydroxy-2,4-dimethoxy-6-methylphenyl)methanone (Ref: 3HDPM)

Major fraction

0.320

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

(5-chloro-2-methoxy-4-methyl-3-pyridyl)(4-(6-O-malonyl-beta-D-glucopyranosyloxy)-2,3-dimethoxy-6-methylphenyl)ketone (Ref: None)

4MGDPM

Plant

(5-chloro-2-methoxy-4-methyl-3-pyridyl)(3-hydroxy-2,4-dimethoxy-6-methylphenyl)ketone (Ref: None)

3HDHP

Plant

2-(5-chloro-2-methoxy-4-methyl-nictotinoyl)-3,4,5-trimethoxybenzaldehyde (Ref: None)

PTBA

Plant

(5-chloro-2-methoxy-4-methyl-3-pyridyl)(3-hydroxy-2,4-dimethoxy-6-methylphenyl)ketone (Ref: None)

3HDPM

Animal (Faeces); Plant; Surface water; Sediment

(5-chloro-2-methoxy-4-methyl-3-pyridyl)(2,3-dihydroxy-4-methoxy-6-methylphenyl)ketone (Ref: None)

4MDPM

Plant

(5-chloro-2-methoxy-4-methyl-3-pyridyl)(2,4-dimethoxy-6-methyl-3-(beta-D-glucopyranosyloxy)phenyl)ketone (Ref: None)

3GDPM

Plant

(5-chloro-2-methoxy-4-methyl-3-pyridyl)(2,3-dimethoxy-6-methyl-4-(beta-D-glucopyranosyloxy)phenyl)ketone (Ref: None)

4GDPM

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

334

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 980 mg kg bw⁻¹ day⁻¹

Unknown species

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

Colinus virginianus

Moderate

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

> 1000

Eisenia foetida

Low

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

32.0

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 1.33 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

1000

range of tested species
Seedling emergence, NOEC
as mg kg⁻¹ soil

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)

> 100

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

> 1035

Aphidius rhopalosiphi

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

> 1000

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)

> 1.44

Oncorhynchus mykiss

Moderate

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

1.27

Pimephales promelas

Moderate

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

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

> 1.55

Daphnia magna

Moderate

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

0.0899

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)

1.6

Chironomus riparius

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)

1.77

Pseudokirchneriella subcapitata Growth

Moderate

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.18

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.07

Rat 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)

Not applicable

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

0.15

Dog SF=100

Dermal penetration studies (%)

0.2-12%

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low for the proposed uses

Occupational

Low for the 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

Rapidly excreted

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver, kidney and blood toxicant
US EPA - not likely to be human carcinogen; CLP data - suspected carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising; Release of toxic and corrosive gases/vapours may occur on combustion; IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H351
Environment: H411

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

pyriofenone

French

pyriofenone

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	26/08/2024
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