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penthiopyrad (Ref: MTF 753)
** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for penthiopyrad

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

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK
Date inclusion expires 30/04/2024
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: USA

Chemical structure: Click here for further information on the general chemical status information used on this site
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: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Carboxamide
Minimum active substance purity 980 g/kg
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 -
CIPAC number 824
US EPA chemical code -
PubChem CID 11388558
Molecular mass (g mol-1) 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 Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) 7
Examples of recorded resistance -
Physical state White powder
Related substances & organisms -

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • DuPont
  • Mitsui Chemicals
Example products using this active
  • Aphet
  • Fontelis
  • Vertisan
  • Velista
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details -


ENVIRONMENTAL FATE

for penthiopyrad

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 1.375 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 402000 A5 - Methanol -
557000 A5 - Acetone -
349000 A5 - Ethyl acetate -
67000 A5 - Toluene -
Melting point (oC) 108.7 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 314 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 4.17 X 1004 Calculated -
Log P 4.62 A5 High
Bulk density (g ml-1)/Specific gravity - - -
Dissociation constant (pKa) at 25oC 10.0 A5 -
Note:
Vapour pressure at 20oC (mPa) 0.000643 A4 - @25 degC Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 7.66 X 10-03 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 2.33 Calculated Transition state
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 1.31 X 10-01 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 Neutral soln.: 226nm=14922
Acidic soln.: 226nm=14460
A5 -
Surface tension (mN m-1) 56.7 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 121.5 A5 Persistent
DT50 (lab at 20oC) 121.5 A5 Persistent
DT50 (field) 9.2 A5 Non-persistent
DT90 (lab at 20oC) 544 A5 -
DT90 (field) 47.6 A5 -
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 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value 3.1 R3 -
Note Oriental melon fruit, n=1
Aqueous photolysis DT50 (days) at pH 7 Value - - -
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable at all relevant pH's
Water-sediment DT50 (days) 269 A5 Slow
Water phase only DT50 (days) 9.9 A5 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd 13.2 A5 Slightly mobile
Koc 804
Notes and range EU dossier Kd range 10-17 mL/g, Koc range 610-1050 mL/g, soils=5
Freundlich Kf 12.52 A5 Slightly mobile
Kfoc 761
1/n 0.96
Notes and range EU dossier Kf range 9.37-14.9 mL/g, Kfoc range 546-919 mL/g, 1/n range 0.94-0.97, Soils=5
pH sensitivity -

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (Ref: IN-DRJ75) This metabolite may cause environmental pollution, click here for further information Soil   0.168   Major fraction; Relevant
N-(2-(3-hydroxy-1,3-dimethyl-butyl)thiophen-3-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide (Ref: 753-T-OH) Soil   0.072   Minor fraction, Relevant
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) Soil   0.081   Minor fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
- dehydro-753-A-OH Rats - -
- hydroxy-MTF-753 Animals; Rats - -
- 753-A-COOH Rats - -
- DM-753-A-COOH Rats - -
- PDA Rats - -
- hydroxy-MTF-753-glucuronide Rats - -
- hydroxy-DM-MTF-753-glucuronide Rats - -
- hydroxy-DM-MTF-753-glucoside Plants - -
- hydroxy-MTF-753-malonyl-glucoside Plants - -
- cys-T-DO Animals - -
- hydroxy-cys-T-DO Rats - -
- dihydroxy-cys-T-DO Animals - -
- GSH-T-DO Rats - -
- N-acetyl-cys-T-DO Rats - -
- cys-F-Do Rats; Animals - -
- dehydro-cys-F-Do Rats; Animals - -
- hydroxy-cys-F-DO Rats; Animals - -
(Ref: IN-DRJ75)
Note: MW=180.08
DM-PCA Soil; Water; Plants; Rats; Animals - -
1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid
(Ref: IN-MR507)
Note: MW=194.11
PCA Soil; Water; Plants; Animals; Rats - -
(Ref: IN-PGH32)
Note: MW=179.10
DM-PAM Rats; Plants; Animals - -
1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide
(Ref: IN-PGH45)
Note: MW=193.13
PAM Soil; Plant; Animal; Rats - -
(Ref: IN-PGH59)
Note: MW=375.34
753-F-DO Soil; Water; Plants; Animals; Rats - -
(Ref: IN-PGH60)
Note: MW=345.39
dihydroxy-753 Plants; Rats; Animals - -


ECOTOXICOLOGY

for penthiopyrad

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 186 A5 Threshold for concern
CT50 (days) 0.65 -
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2250 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 0.29 A5 Pimephales promelas Moderate
Fish - Chronic 21 day NOEC (mg l-1) - - -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 1.38 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (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) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) - - -
Non-target plants > 1563 A5 Lolium perenne
Seedling emergence, EC50
as g/ha
-
> 1563 A5 Triticum aestivum
Vegetative vigour, EC50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) > 1.58 A5 Pseudokirchneriella subcapitata 96hr 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) > 500 A5 Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 500 A5 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) > 500 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) > 48 A5 Eisenia foetida Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 327.1 A5 Typhlodromus pyri, as product -
% Effect - - -
Other arthropod (2) LR50 g ha-1 2800 A5 Aphidius rhopalosiphi -
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: EC25 100-333 mg kg-1
Carbon mineralisation: No significant adverse effect
A5 -
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for penthiopyrad

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.59 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.1 A5 Rat, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.75 A5 Rat, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.1 A5 Rat, SF=100 -
Dermal penetration studies (%) Up to 53% A5 -
Dangerous Substances Directive 76/464 List II - -
Exposure Routes Public Acceptable for proposed uses
Occupational PPE/PPC recommended
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A3; B3; C3; D0; E3

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Possible liver toxicant
USEPA - some evidence to suggest possible human carcinogen
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative
Key: Other
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
CLP classification 2013 Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Carcinogen category 2: R40
N - Dangerous for the environment: R50/53
EC Safety Classification Click here to view information omn the EU safety phrases None allocated at this time
WHO Classification NL - Not listed
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for penthiopyrad

Language Name
English penthiopyrad
French -
German -
Danish -
Italian -
Spanish -
Greek -
Slovenian -
Polish -
Swedish -
Hungarian -
Dutch -

Record last updated: Wednesday 26 June 2019
Contact: aeru@herts.ac.uk