Pyriofenone (Ref: IKF-309)

Pyriofenone (Ref: IKF-309)	Last updated: 11/11/2019
(Not known by any other names)

GENERAL INFORMATION

Description

A novel 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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

31/01/2024

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
✓		✓	✓	✓	✓	✓	✓

Also used in

Chemical structure

Isomerism

Chemical formula

C₁₈H₂₀ClNO₅

Canonical SMILES

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

Isomeric SMILES

No data

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 group

Benzoylpyridine

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

CIPAC number

827

US EPA chemical code

PubChem CID

23082663

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 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

White crystalline powder

Formulations

Property

Value

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

IKF-309 180SC
property

Example products using this active

ISK Biosciences Europe NV
Belchim Crop Protection

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)

Not expected to self ignite; Not highly flammable

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

1.58 X 10⁰³

Calculated

Log P

3.2

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

21.9

Slightly mobile

K_foc

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

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.225

Major fraction, No relevant

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

Soil

0.320

Major fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

(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; Soil; 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

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

160

Threshold for concern

CT₅₀ (days)

Not available

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

Collinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 980 mg kg⁻¹ BW/day

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

Colinus virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 1.44

Oncorhynchus mkkiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

1.27

Pimephales promelas

Moderate

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

> 1.55

Daphnia magna

Moderate

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

0.0899

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)

1.6

Chironomus riparius

Moderate

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

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

Non-target plants

1000

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

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

1.77

Pseudokirchneriella subcapitata growth

Moderate

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

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)

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)

> 1000

Eisenia foetida

Low

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

32.0

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

1000

>
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

1035

>
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 1.33mg kg⁻¹ soil 28days

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)

> 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)

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

European MRLs

EU MRL pesticide database

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

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
USEPA - not likley to be human 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 Code is usually 9

CLP classification 2013

Environment: H411

EC Risk Classification

Carcinogen category 3: R40
N - Dangerous for the environment: R51, R52, R53

EC Safety Classification

S13, S35, S36, S37, S57

WHO Classification

NL (Not listed)

UN Number

3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

pyriofenone

French

pyriofenone

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	11/11/2019
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