Pydiflumetofen (Ref: SYN 545794)

Pydiflumetofen (Ref: SYN 545794)	Last updated: 10/12/2020
(Also known as: adepidyn )

SUMMARY

Pydiflumetofen is a new fungicide currently being assessed for safety and efficacy in the EU. It has a low aquesous 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.

GENERAL INFORMATION

Description

A new broad spectrum fungicide for use on various field crops

Example pests controlled

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

Example applications

Soybeans; Cereals; Vegetables; 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

Novel

Introduction & key dates

2016

UK regulatory status

UK COPR regulatory status

Pending

Date COPR inclusion expires

UK LERAP status

No UK approval for use

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

Also used in

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

Chemical structure

Isomerism

Two enantiomers marketed as a racemate mixture

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

No data

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

Substance group

Carboxamide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier: None declared

Substance origin

Synthetic

Mode of action

Succinate dehydrogenase inhibitor

CAS RN

1228284-64-7

EC number

CIPAC number

US EPA chemical code

PubChem CID

56933411

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 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

Off-white coloured powdery solid

Formulations

Property

Value

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

Miravis

Example products using this active

Syngenta

Formulation and application details

Usually formulated as a suspension 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)

113

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

6.31 X 10⁰³

Calculated

Log P

3.8

at 25 °C

High

Bulk 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)

1.05 X 10^-04

Non-volatile

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

Acidic soln: 230nm=18267

Surface tension (mN m⁻¹)

71.5

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradeable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

2416

Very persistent

DT₅₀ (lab at 20 °C)

2416

Very persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

7300

Very persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

1440

geometric mean

Note

EU 2017 dossier Lab studies DT₅₀ range 469-4170 days,, DT₉₀ range 1560 - >10000 days, Soils=5

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ 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)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

25.2

Slightly mobile

K_foc

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

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.57

Calculated

Transition state

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

Value

1.51 X 10^-01

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2,4,6-trichlorphenol

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

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

Animal; Rat

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

Plant; Water

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 500

Rat

Moderate

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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.18

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.42

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (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

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

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

> 5.9

Pseudokirchneriella subcapitata

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 meliifera

Low

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

> 100

Apis meliifera

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)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

408

>
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

408

>
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 500

Rat

Moderate

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

500

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)

0.092

Mouse SF=100

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

0.1

Rabbit SF=100

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

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

0.1

Rabbit SF=100

Dermal penetration studies (%)

0.2-1.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

General human health issues

Possible liver & thyroid toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

EC Safety Classification

WHO Classification

High (class III)

UN Number

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

pydiflumetofen

French

pydiflumetofene

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	10/12/2020
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