Page last updated: 2024-11-12

penthiopyrad

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

penthiopyrad: a fungicide [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

penthiopyrad : A racemate comprising equimolar amounts of (R)- and (S)-penthiopyrad. Used to control rust and Rhizoctonia diseases and also shows activity against grey mould, powdery mildew and apple scab. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide : An aromatic amide obtained by formal condensation of the carboxy group of 1-methyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid with the amino group of 2-(4-methylpentan-2-yl)thiophen-3-amine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID11388558
CHEMBL ID2251844
CHEBI ID83138
SCHEMBL ID18701
MeSH IDM0533701

Synonyms (37)

Synonym
penthiopyrad
chebi:83138 ,
bdbm50079600
1-methyl-n-[2-(4-methylpentan-2-yl)thiophen-3-yl]-3-(trifluoromethyl)pyrazole-4-carboxamide
183675-82-3
fat7900e5h ,
unii-fat7900e5h
penthiopyrad [iso]
C18482
AKOS015914702
1135441-67-6
n-(2-(1,3-dimethylbutyl)-3-thienyl)-1-methyl-3-(trifluoromethyl)-1h-pyrazole-4-carboxamide
dpx-lem 17
penthiopyrad [mi]
1h-pyrazole-4-carboxamide, n-(2-(1,3-dimethylbutyl)-3-thienyl)-1-methyl-3-(trifluoromethyl)-
vertisan
mtf-753
gaia
HY-17520
CS-3306
SCHEMBL18701
CHEMBL2251844
1-methyl-n-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)-1h-pyrazole-4-carboxamide
1-methyl-n-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide
DTXSID6058005
AC-25642
mfcd11973641
n-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-1h-pyrazole-4-carboxamide
penthiopyrad, pestanal(r), analytical standard
(rs)-n-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide
J-011771
PFFIDZXUXFLSSR-UHFFFAOYSA-N ,
BCP13108
penthiopyrad 100 microg/ml in acetonitrile
Q14075651
MS-25662
1h-pyrazole-4-carboxamide, n-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-

Research Excerpts

Overview

Penthiopyrad is a broad-spectrum fungicide with wide application in agriculture with preferential degradation of the S (+)-stereoisomer in soil. It is a widely used chiral fungicide for controlling rust and Rhizoctonia diseases.

ExcerptReferenceRelevance
"Penthiopyrad is a widely used succinate dehydrogenase inhibitor (SDHI) fungicide and frequently detected in natural environments. "( Degradation pathways of penthiopyrad by δ-MnO
An, T; Chen, Z; Gao, Z; Gu, F; Song, H; Xu, R; Zhao, M; Zheng, S, 2021
)
2.37
"Penthiopyrad is a broad-spectrum fungicide with wide application in agriculture with preferential degradation of the S (+)-stereoisomer in soil. "( Dissipation, residue, stereoselectivity and dietary risk assessment of penthiopyrad and metabolite PAM on cucumber and tomato in greenhouse and field.
Dou, L; Lan, T; Li, J; Yang, G; Zhang, K, 2022
)
2.4
"Penthiopyrad is a widely used chiral fungicide for controlling rust and Rhizoctonia diseases. "( Fertilization can modify the enantioselective persistence of penthiopyrad in relation to the co-influence on soil ecological health.
Chen, K; Li, Y; Liu, H; Liu, M; Shan, M, 2023
)
2.59
"Penthiopyrad is a widely used succinic dehydrogenase inhibitor fungicide with two enantiomers, while the data on its enantioselective behaviors in crops are limited. "( Enantioselective Behaviors of Chiral Fungicide Penthiopyrad in Five Kinds of Crops and Whole-Age Dietary Risk Assessments.
Cang, T; Di, S; Diao, Z; Liu, Z; Qi, P; Wang, X; Wang, Z; Xu, H; Zhang, C; Zhao, H, 2023
)
2.61
"Penthiopyrad is a novel chiral succinate dehydrogenase inhibitor (SDHI) fungicide with two enantiomers. "( Rational understanding of chiral fungicide penthiopyrad stereoselectivity: Bioactivity, aquatic toxicity and cytotoxicity.
An, X; Dong, F; Guo, P; Pan, X; Wu, X; Xu, J; Zheng, Y, 2023
)
2.62
"Penthiopyrad is a chiral carboxamide fungicide with a broad spectrum of fungicidal activity. "( Stereoselective degradation behavior of the novel chiral antifungal agrochemical penthiopyrad in soil.
Chen, D; Chen, Y; Han, J; Liu, Z; Zhang, K, 2021
)
2.29

Dosage Studied

ExcerptRelevanceReference
"The results indicated that at the same efficacy, the optically pure S-(+)-PEN could lower the dosage of racemate by 20-96%."( Systemic enantioselectivity study of penthiopyrad: enantioselective bioactivity, acute toxicity, degradation and influence on tomato.
Deng, Y; Diao, J; Liu, R; Liu, Y; Nie, Y; Wang, Z; Wu, D; Yu, S; Zhou, Z; Zhu, W, 2023
)
1.18
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
aromatic amideAn amide in which the amide linkage is bonded directly to an aromatic system.
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
pyrazoles
thiophenesCompounds containing at least one thiophene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrialSus scrofa (pig)IC50 (µMol)0.52700.52700.52700.5270AID1202116
Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrialSus scrofa (pig)Ki0.32700.32700.32700.3270AID1202117
Succinate dehydrogenase cytochrome b560 subunit, mitochondrialSus scrofa (pig)IC50 (µMol)0.52700.52700.52700.5270AID1202116
Succinate dehydrogenase cytochrome b560 subunit, mitochondrialSus scrofa (pig)Ki0.32700.32700.32700.3270AID1202117
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1112880Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1202113Inhibition of porcine heart SQR in SCR complex assessed as reduction in ubiquinol-cytochrome c reductase (complex 3) activity by measuring cytochrome c level using succinate and DCIP substrate by spectrophotometry2015European journal of medicinal chemistry, May-05, Volume: 95Discovery of N-benzoxazol-5-yl-pyrazole-4-carboxamides as nanomolar SQR inhibitors.
AID1202118Inhibition of porcine heart electron transport protein complex 3 in SCR complex at 10 uM using DBH2 and cytochrome c substrate by spectrophotometry2015European journal of medicinal chemistry, May-05, Volume: 95Discovery of N-benzoxazol-5-yl-pyrazole-4-carboxamides as nanomolar SQR inhibitors.
AID1112891Fungicidal activity against Oculimacula yallundae assessed as inhibition of germ tube elongation incubated at 19 degC in dark for 48 hr2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112878Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1666590Inhibition of porcine succinate-ubiquinone oxidoreductase using succinate and 2,6-dichloroindophenol as substrates by spectrophotometric based assay2020Bioorganic & medicinal chemistry, 03-01, Volume: 28, Issue:5
N-(3,5-Dichloro-4-(2,4,6-trichlorophenoxy)phenyl)benzenesulfonamide: A new dual-target inhibitor of mitochondrial complex II and complex III via structural simplification.
AID1666592Inhibition of porcine cytochrome b-c1 complex at 10 uM using DBH2 and cytochrome c as substrates by spectrophotometric based assay relative to control2020Bioorganic & medicinal chemistry, 03-01, Volume: 28, Issue:5
N-(3,5-Dichloro-4-(2,4,6-trichlorophenoxy)phenyl)benzenesulfonamide: A new dual-target inhibitor of mitochondrial complex II and complex III via structural simplification.
AID1666589Inhibition of porcine succinate-cytochrome c reductase using succinate and cytochrome c as substrates by spectrophotometric based assay2020Bioorganic & medicinal chemistry, 03-01, Volume: 28, Issue:5
N-(3,5-Dichloro-4-(2,4,6-trichlorophenoxy)phenyl)benzenesulfonamide: A new dual-target inhibitor of mitochondrial complex II and complex III via structural simplification.
AID1375027Inhibition of porcine succinate-cytochrome c reductase using succinate and cytochrome c as substrate by spectrophotometric analysis2018Bioorganic & medicinal chemistry letters, 05-01, Volume: 28, Issue:8
Synthesis of new 4-aryloxy-N-arylanilines and their inhibitory activities against succinate-cytochrome c reductase.
AID1375030Inhibition of porcine succinate-cytochrome c reductase complex 3 at 10 uM using decylubiquinol and cytochrome c as substrate by spectrophotometric analysis relative to control2018Bioorganic & medicinal chemistry letters, 05-01, Volume: 28, Issue:8
Synthesis of new 4-aryloxy-N-arylanilines and their inhibitory activities against succinate-cytochrome c reductase.
AID1112881Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 to EC50 for wild type Oculimacula yallundae TriS by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1202116Inhibition of porcine heart SQR in SCR complex assessed as reduction in ubiquinol-cytochrome c reductase (complex 3) activity by measuring cytochrome c level using succinate and DCIP substrate at 23 degC by spectrophotometry2015European journal of medicinal chemistry, May-05, Volume: 95Discovery of N-benzoxazol-5-yl-pyrazole-4-carboxamides as nanomolar SQR inhibitors.
AID1202115Non-competitive inhibition of porcine heart SCR with respect to cytochrome c substrate at 23 degC by double-reciprocal plot2015European journal of medicinal chemistry, May-05, Volume: 95Discovery of N-benzoxazol-5-yl-pyrazole-4-carboxamides as nanomolar SQR inhibitors.
AID1375028Inhibition of porcine succinate-cytochrome c reductase at 10 uM using succinate and cytochrome c as substrate by spectrophotometric analysis relative to control2018Bioorganic & medicinal chemistry letters, 05-01, Volume: 28, Issue:8
Synthesis of new 4-aryloxy-N-arylanilines and their inhibitory activities against succinate-cytochrome c reductase.
AID1202117Non-competitive inhibition of porcine heart SQR in SCR complex with respect to DCIP substrate at 23 degC by double-reciprocal plot2015European journal of medicinal chemistry, May-05, Volume: 95Discovery of N-benzoxazol-5-yl-pyrazole-4-carboxamides as nanomolar SQR inhibitors.
AID1202114Inhibition of porcine heart SCR using succinate and cytochrome c substrate at 23 degC by spectrophotometry2015European journal of medicinal chemistry, May-05, Volume: 95Discovery of N-benzoxazol-5-yl-pyrazole-4-carboxamides as nanomolar SQR inhibitors.
AID1375029Inhibition of porcine succinate-cytochrome c reductase complex 2 at 10 uM using succinate and dichlorophenolindophenol as substrate by spectrophotometric analysis relative to control2018Bioorganic & medicinal chemistry letters, 05-01, Volume: 28, Issue:8
Synthesis of new 4-aryloxy-N-arylanilines and their inhibitory activities against succinate-cytochrome c reductase.
AID1112877Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112879Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 by germ tube elongation assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (34)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (2.94)29.6817
2010's15 (44.12)24.3611
2020's18 (52.94)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.78

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.78 (24.57)
Research Supply Index3.56 (2.92)
Research Growth Index6.19 (4.65)
Search Engine Demand Index56.78 (26.88)
Search Engine Supply Index3.17 (0.95)

This Compound (31.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other32 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]