Penthiopyrad (Ref: MTF 753)

Penthiopyrad (Ref: MTF 753)	Last updated: 31/10/2024
(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: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

Used to control rust, Rhizoctonia diseases and other fungal diseases on cereals and other crops

Example pests controlled

Rust; Rhizoctonia diseases; Grey mould; Powdery mildew; Applie scab; Septoria leaf blotch

Example applications

Cereals including wheat; Potatoes; Sugarbeet; Turf; Legumes; Vegetables; Soybeans

Efficacy & activity

Wheat/Septoria=High; Wheat/Rust=Moderate; Barley/Rhynchosporium=Moderate; Barley/Mildew=Low; Barley/Rust=Moderate; Barley/Net blotch=Moderate; Barley/Ramularia=Moderate

Availability status

Current

Introduction & key dates

circa 2003, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/05/2031

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Sweden/Czech Republic

Date EC 1107/2009 inclusion expires

31/05/2025

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

USA

Chemical structure

Isomerism

Penthiopyrad is a chiral molecule. The technical material is an isomeric mixture of the R- and S-enantiomers..

Chemical formula

C₁₆H₂₀F₃N₃OS

Canonical SMILES

CC(C)CC(C)C1=C(C=CS1)NC(=O)C2=CN(N=C2C(F)(F)F)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

PFFIDZXUXFLSSR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H20F3N3OS/c1-9(2)7-10(3)13-12(5-6-24-13)20-15(23)11-8-22(4)21-14(11)16(17,18)19/h5-6,8-10H,7H2,1-4H3,(H,20,23)/f/h20H

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Carboxamide fungicide; Pyrazolecarboximide fungicide; Thiophene fungicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

Broad spectrum, preventative and curative; inhibits mitochondrial functions - Succinate Dehydrogenase Inhibitor (SDHI)

CAS RN

183675-82-3

EC number

606-001-8

CIPAC number

824

US EPA chemical code

PubChem CID

11388558

CLP index number

616-222-00-1

Molecular mass

359.4

PIN (Preferred Identification Name)

rac-1-methyl-N-{2-[(2R)-4-methylpentan-2-yl]thiophen-3-yl}-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide

IUPAC name

(RS)-N-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide

CAS name

N-(2-(1,3-dimethylbutyl)-3-thienyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide

Other status information

PAN listed Highly Hazardous Chemical

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 powder

Formulations

Property

Value

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

DuPont
Mitsui Chemicals

Example products using this active

Aphet
Affet
Fontelis
Vertisan
Velista
Gaia

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.375

Low

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

402000

Methanol

557000

Acetone

349000

Ethyl acetate

67000

Toluene

Melting point (°C)

108.7

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

314

Flashpoint (°C)

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

4.17 X 10⁰⁴

Calculated

Log P

4.62

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data - studies show residues do not accumulate in fat

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

10.0

Vapour pressure at 20 °C (mPa)

0.00643

at 25 °C

Low volatility

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

7.66 X 10^-03

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 soln.: 226nm=14922
Acidic soln.: 226nm=14460

Surface tension (mN m⁻¹)

56.7

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

121.5

Persistent

DT₅₀ (lab at 20 °C)

121.5

Persistent

DT₅₀ (field)

9.2

Non-persistent

DT₉₀ (lab at 20 °C)

544

Very persistent

DT₉₀ (field)

47.6

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 50.8-340.5 days, DT₉₀ range 217->1000 days; Field studies DT₅₀ range 0.8-33.3 days, DT₉₀ range 7.2-169 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.2

Note

Published literature RL₅₀ range 3.1-5.4 days, 2 field crops, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Stable

Note

Stable at all relevant pH's

Water-sediment DT₅₀ (days)

269

Slow

Water phase only DT₅₀ (days)

9.9

Moderately fast

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

[Pear homogenate: No observed residue decay @ <=20 DegC after 7 days; Lab study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

13.2

Slightly mobile

K_oc (mL g⁻¹)

804

Notes and range

EU dossier K_d range 10-17 mL g⁻¹, K_oc range 610-1050 mL g⁻¹, soils=5

Freundlich

K_f (mL g⁻¹)

12.52

Slightly mobile

K_foc (mL g⁻¹)

761

¹/_n

0.96

Notes and range

EU dossier K_f range 9.37-14.9 mL g⁻¹, K_foc range 546-919 mL g⁻¹, ¹/_n range 0.94-0.97, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.08

Calculated

Low leachability

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

Value

1.36 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

3.096

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)

186

Threshold for concern

CT₅₀ (days)

0.65

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

N-[2-(1-hydroxymethyl-1,3-dimethylbutyl)thiophen-3-yl]-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide

Minor fraction

0.043

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide

Major fraction

0.182

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid

Major fraction

0.345

3-trifluoromethyl-1H-pyrazole-4-carboxylic acid

Major fraction

0.388

3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Ref: IN DRJ75)

Major fraction

0.280

N-(2-(3-hydroxy-1,3-dimethyl-butyl)thiophen-3-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide (Ref: 753-A-OH)

Minor fraction

0.072

3-methyl-1-{3-[(1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]thiophen-2-yl}pentanoic acid

Minor fraction

0.054

N-(5-hydroxy-5-(1,3-dimethylbutyl)-2-oxo-2,5-dihydrothiophen-4-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide (Ref: 753-T-DO)

Minor fraction

0.081

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide (Ref: IN-PGH45)

Not relevant

0.006

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Ref: IN-MR507)

Not relevant

3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Ref: IN-DRJ75)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Ref: IN-MR507)
Note: MW=194.11

PCA

Water; Plant; Animal; Rat

-
Note: MW=375.41

hydroxy-MTF-753

Animal; Rat

Ref: IN-PGH60
Note: MW=345.39

dihydroxy-753

Plant; Rat; Animal

-
Note: MW=389.40

753-A-COOH

Rat

-
Note: MW=375.37

DM-753-A-COOH

Rat

Ref: IN-PGH32
Note: MW=179.10

DM-PAM

Rat; Plant; Animal

Ref: IN-DRJ75
Note: MW=180.08

DM-PCA

Water; Plant; Rat; Animal

-
Note: MW=98.10

PDA

Rat

-
Note: MW=551.53

hydroxy-MTF-753-glucuronide

Rat

-
Note: MW=537.51

hydroxy-DM-MTF-753-glucuronide

Rat

-
Note: MW=698.73

GSH-T-DO

Rat

-
Note: MW=554.60

N-acetyl-cys-T-DO

Rat

-
Note: MW=496.50

cys-F-Do

Rats; Animals

-
Note: MW=478.49

dehydro-cys-F-Do

Rats; Animals

-
Note: MW=512.50

hydroxy-cys-F-DO

Rats; Animals

-
Note: MW=511.57

cys-T-DO

Animal

-
Note: MW=528.57

hydroxy-cys-T-DO

Rat

-
Note: MW=544.57

dihydroxy-cys-T-DO

Animal

-
Note: MW=523.52

hydroxy-DM-MTF-753-glucoside

Plant

-
Note: MW=609.58

hydroxy-MTF-753-malonyl-glucoside

Plant

1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide (Ref: IN-PGH45)
Note: MW=193.13

PAM

Plant; Animal; Rat

Ref: IN-PGH59
Note: MW=375.34

753-F-DO

Water; Plant; Animal; Rat

-
Note: MW=357.39

dehydro-753-A-OH

Rat

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)

278

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

206.8

Anas platyrhynchos NOAEL

Low

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

> 500

Eisenia foetida corr

Moderate

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

> 48

Eisenia foetida

Moderate

Soil micro-organisms

Nitrogen mineralisation: EC25 100-333 mg kg⁻¹
Carbon mineralisation: No significant adverse effect

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 1563

Lolium perenne
Seedling emergence, EC₅₀
as g ha⁻¹

> 1563

Triticum aestivum
Vegetative vigour, EC₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 500

Apis mellifera

Low

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

> 500

Apis mellifera

Low

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

Chronic

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) as Mortality LR₅₀ g ha⁻¹

> 2340

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 3504.5

Aphidius rhopalosiphi

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

327.1

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)

0.29

Pimephales promelas

Moderate

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

0.051

Pimephales promelas

Moderate

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

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

> 1.38

Daphnia magna

Moderate

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

0.47

Daphnia magna as NOAEC

Moderate

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

1.7

Mysidopsis bahia

Moderate

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)

50.0

Chironomus riparius 21 day NOAEC

Moderate

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

1.21

Lemna gibba Chronic

Moderate

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

> 1.58

Pseudokirchneriella subcapitata 96 hr

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.59

Rat

Other Mammal toxicity endpoints

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

0.1

Rat SF=100

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

0.75

Rat SF=100

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)

0.1

Rat SF=100

Dermal penetration studies (%)

Up to 53%

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Acceptable for proposed uses

Occupational

PPE/PPC recommended

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL expected to deviate from the EU MRL in mid-2023

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapid and extensive via bile & faeces

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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 toxicant
US EPA - weak evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

penthiopyrad

French

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