Pydiflumetofen (Ref: SYN 545794)

Pydiflumetofen (Ref: SYN 545794)	Last updated: 31/10/2024
(Also known as: adepidyn )

SUMMARY

Pydiflumetofen is a broad-spectrum fungicide. It has a low aqueous solubility and a low volatility. It may be persistent in both soil and water systems depending upon local conditions. It is not highly toxic to mammals but it may be a liver and/or thyroid toxicant. It is highly toxic to most aquatic species.

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: Very persistent; Potential for particle bound transport: High	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Possible Carcinogen; Reproduction/development effects

GENERAL INFORMATION

Description

A broad spectrum fungicide for use on various field crops for treating a wide range of plant diseaes

Example pests controlled

Powdery mildew (Uncinula necator); Septoria, Cercospora leaf spot; Alternaria; Scab (venturia pyrina); Grey mould (Botrytis cinerea)

Example applications

Soybeans; Cereals including barley, oats, wheat, rye, triticale; Vegetables including carrots, parsnip; Corn; Peanut; Curcubits; Potato; Top fruit; Grapes; Melon; Yam

Efficacy & activity

Syngenta claims it provides long-lasting disease control and crop enhancement benefits to enable higher potential yield.

Availability status

Current

Introduction & key dates

2016, introduced; 2024, first UK approval

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

02/04/2031

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Pending

Dossier rapporteur/co-rapporteur

France/Austria

Date EC 1107/2009 inclusion expires

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

Argentina, Uruguay, Argentina, Australia, Canada, New Zealand, USA

Chemical structure

Isomerism

Two enantiomers (SYN546968 and SYN546969) marketed as a racemate

Chemical formula

C₁₆H₁₆Cl₃F₂N₃O₂

Canonical SMILES

CC(CC1=C(C=C(C=C1Cl)Cl)Cl)N(C(=O)C2=CN(N=C2C(F)F)C)OC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

DGOAXBPOVUPPEB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H16Cl3F2N3O2/c1-8(4-10-12(18)5-9(17)6-13(10)19)24(26-3)16(25)11-7-23(2)22-14(11)15(20)21/h5-8,15H,4H2,1-3H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
pydiflumetofen	-

General status

Pesticide type

Fungicide, Plant Growth Regulator

Substance groups

Carboxamide fungicide; Pyrazole fungicide; Pyrazolecarboximide fungicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier: None declared

Substance origin

Synthetic

Mode of action

Succinate Dehydrogenase Inhibitor (SDHI)

CAS RN

1228284-64-7

EC number

817-852-1

CIPAC number

999

US EPA chemical code

PubChem CID

56933411

CLP index number

No data found

Molecular mass

426.67

PIN (Preferred Identification Name)

3-(difluoromethyl)-N-methoxy-1-methyl-N-((2E)-1-(2,4,6-trichlorophenyl)propan-2-yl)-1H-pyrazole-4-carboxamide

IUPAC name

3-(difluoromethyl)-N-methoxy-1-methyl-N-((RS)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl)pyrazole-4-carboxamide

CAS name

3-(difluoromethyl)-N-methoxy-1-methyl-N-(1-methyl-2-(2,4,6-trichlorophenyl)ethyl)-1H-pyrazole-4-carboxamide

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

Off-white coloured powdery solid

Formulations

Property

Value

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

Syngenta

Example products using this active

Miravis Plus
Adepidyn

Formulation and application details

Usually formulated as a suspension or emulsifiable concentrate and applied as a foliar spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.5

at 25 °C

Low

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

220000

Acetone

130000

Ethyl acetate

26000

methanol

7200

Octanol

Melting point (°C)

112.7

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

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

6.31 X 10⁰³

Calculated

Log P

3.8

at 25 °C

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.84 X 10^-04

Low volatility

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

1.51 X 10^-07

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Acidic soln: 230nm=18267
Neutral soln: 230nm=17736
Basic soln: 230nm=17850

Surface tension (mN m⁻¹)

71.5

at 21°C 99.5%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradeable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

930

Very persistent

DT₅₀ (lab at 20 °C)

930

Very persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

3210

Very persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

930

geometric mean

Note

GB HSE 2023 dossier: Lab studies DT₅₀ (normalised) range 398-1690 days, DT₉₀ (measured) range 1320-5600 days, Soils=5; EU 2017 dossier Lab studies DT₅₀ range 398-2380 days, DT₉₀ range 1320-7640 days, Soils=5

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

Stable

Note

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

Value

Stable

Note

Stable at all environmentally relevant pH values

Water-sediment DT₅₀ (days)

662

Stable

Water phase only DT₅₀ (days)

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)

25.2

Slightly mobile

K_foc (mL g⁻¹)

1738

¹/_n

0.88

Notes and range

EU 2017 dossier K_f range 11.76-36.1 mK/g, K_foc range 1165-2206 mL g⁻¹, ¹/_n range 0.84-0.89, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.26

Calculated

Transition state

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

Value

1.21 X 10^-01

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

5.85

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)

CT₅₀ (days)

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-[[3-(difluoromethyl)-1-methyl-pyrazole-4-carbonyl]amino]butanoic acid (Ref: SYN548262)

Water (aqueous photolysis)

3-[[3-(difluoromethyl)-1-methyl-pyrazole-4-carbonyl]-methoxy-amino]butanoic acid (Ref: SYN548261)

Surface water (photolysis)

3-(difluoromethyl)-N-[2-hydroxy-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-N-methoxy-1-methyl-pyrazole-4-carboxamide (Ref: SYN547948)

CSCY608054

Rat; Animal

3-(difluoromethyl)-N-methoxy-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide Glucuronide conjugate (Ref: SYN547891)

Rat (minor); Animal

3-(difluoromethyl)-N-(2-hydroxy-1-methyl-ethyl)-N-methoxy-1-methyl-pyrazole-4-carboxamide (Ref: SYN548265)

Rat

N-[2-(2,4-dichlorophenyl)-1-methyl-ethyl]-3-(difluoromethyl)-N-methoxy-1-methyl-pyrazole-4-carboxamide (Ref: SYN547893)

CSCD677133

Rat

N-[2-(2,6-dichloro-4-hydroxy-phenyl)-1-methyl-ethyl]-3-(difluoromethyl)-N-methoxy-1-methyl-pyrazole-4-carboxamide (Ref: SYN547894)

CSCV764141

Rat

3-(difluoromethyl)-1-methyl-N-(1-methyl-2- (2,4,6-trichlorophenyl) ethyl) pyrazole-4-carboxamide (Ref: SYN545547)

Plant; Water

3-difluoromethyl-1-methyl-1H-pyrazole-4- carboxylic acid amide (Ref: SYN508272)

Animal; Rat

(R)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-amide (Ref: SYN546969)

CSCD746375

Enantiomer of pydiflumetofen

(S)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-amide (Ref: SYN546968)

CSCD746374

Enantiomer of pydiflumetofen

2,4,6-trichlorphenol

2,4,6-TCP

Rat: Animal

3-difluoromethyl-1-methyl-1H-pyrazole-4- carboxylic acid (Ref: NOA449410)

Rat; Water

2-((3-(difluoromethyl)-1-methyl-pyrazole-4- carbonyl)-methoxy-amino)propanoic acid (Ref: SYN548263)

Rat; Animal

2-((3-(difluoromethyl)-1-methyl-pyrazole-4- carbonyl) amino)propanoic acid (Ref: SYN548264)

Milk; Animal

3-difluoromethyl-1-methyl-1H-pyrazole-4- carboxylic acid methoxy-(1-methyl-2- (2,4,6-trichloro-3-hydroxy-phenyl)-ethyl)- amide (Ref: SYN547897)

Animal commodities; Rat

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)

3776

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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)

31.81

Eisenia foetida 56 day

Moderate

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

186.0

Folsomia candida

Non-target plants

> 200

Brassica oleracea Beta vulgaris Brassica napus Lycopersicon esculentum Lactuca sativa
Vegetative vigour, ER₅₀
as g ha⁻¹

> 200

Brassica oleracea Beta vulgaris Brassica napus Lycopersicon esculentum Lactuca sativa
Seedling emergence, ER₅₀
as g ha⁻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)

> 116

Apis mellifera

Low

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

Chronic as 10-day LC₅₀ µg bee⁻¹ day⁻¹

> 138.2

Apis mellifera

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

> 408

Aphidius rhopalosiphi

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

> 408

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)

0.18

Oncorhynchus mykiss

Moderate

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

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

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

0.42

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)

0.16

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.69

Chironomus riparius

Moderate

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)

> 6.3

Lemna gibba

Moderate

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

> 5.9

Pseudokirchneriella subcapitata

Moderate

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

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.11

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.09

Mouse SF=100

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

0.3

Rat SF=100

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

0.15

Rat SF=100

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

0.05

Rabbit SF=100

Dermal penetration studies (%)

0.4-11.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Changes to GB MRL implemented April 2024

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapidly excreted via faeces, bile & urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible liver & thyroid toxicant
CLP & GB HSE data: suspected of causing cancer

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Health: H351, H361f
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

pydiflumetofen

French

pydiflumetofene

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	31/10/2024
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