Page last updated: 2024-12-11

prothioconazole

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

Description

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

prothioconazole : A racemate comprising equal amounts of (R)- and (S)-prothioconazole. A fungicide for use both as a seed treatment and foliar spray to treat a variety of diseases in cereals. [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]

2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione : A member of the class of triazoles that is 1,2,4-triazole-3-thione substituted at position 2 by a 2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl group. [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 CID6451142
CHEMBL ID2251446
CHEBI ID84008
SCHEMBL ID21497
MeSH IDM0547223

Synonyms (50)

Synonym
prothioconazole
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1h-1,2,4-triazole-3-thione
prothioconazole (2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1,2-dihydro-3h-1,2,4-triazole-3-thione)
2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1,2-dihydro-3h-1,2,4-triazole-3-thione
27b9fv58iy ,
jau 6476
prothioconazole [iso:bsi]
unii-27b9fv58iy
proline 480 sc fungicide
hsdb 7893
178928-70-6
C18888
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxy-propyl]-4h-1,2,4-triazole-3-thione
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-3h-1,2,4-triazole-3-thione
chebi:84008 ,
CHEMBL2251446
prothioconazole [mi]
prothioconazole [iso]
jau-6476
3h-1,2,4-triazole-3-thione, 2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1,2-dihydro-
(rs)-2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-2,4-dihydro-1,2,4-triazole-3-thione
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione
2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1h-1,2,4-triazole-3(2h)-thione
SCHEMBL21497
2-(1-chloro-cyclopropyl)-1(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol
2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1 ,2,4-triazol-1-yl)-propan-2-ol
2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol
2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol
tox21_303849
NCGC00357118-01
cas-178928-70-6
dtxsid4034869 ,
dtxcid2014869
AKOS024462906
FT-0696709
3h-1,2,4-triazole-3-thione, 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-
mfcd08273847
J-011412
pesticide5_prothioconazole_c14h15cl2n3os_redigo
DS-9631
Q10816580
AMY3562
D78065
hsdb7893
hsdb-7893
A902200
2-[2-(1-chloro-cyclopropyl)-3-(2-chlorophenyl)-2-hydroxy-propyl]-1,2-dihydro-3h-1,2,4-triazol-3-thione;2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1h-1,2,4-triazole-3(2h)-thione
CS-0065913
c14h15cl2n3os
AKOS040744510

Research Excerpts

Overview

Prothioconazole (PTC) is a widely used chiral triazole fungicide. Its parent and metabolite prothiconazole-desthio (dPTC), have been detected in diverse environmental media. ProthiConazole is a new type of triazolinthione fungicide used worldwide.

ExcerptReferenceRelevance
"Prothioconazole (PTC) is a high effective systemic fungicide, and one of its major metabolites is prothioconazole-desthio (PTC-d). "( Toxicological effects of acute prothioconazole and prothioconazole-desthio administration on liver in male Chinese lizards (Eremias argus).
Chang, J; Hao, W; Li, J; Pan, Y; Xie, Y, 2022
)
2.45
"Prothioconazole (PTC) is a new broad-spectrum triazole antibacterial agent that is being widely used in agriculture. "( Prothioconazole induces cell cycle arrest by up-regulation of EIF4EBP1 in extravillous trophoblast cells.
Dong, G; Du, G; Hu, Q; Lu, C; Martin, EM; Qin, Y; Wang, X; Xia, Y; Zhang, R, 2022
)
3.61
"Prothioconazole is a widely used chiral triazole fungicide, and its residue pollution has attracted wide attention in recent years. "( Isolation of Sphingomonas sp. AJ-1 and its enantioselective S-methylation of the triazole fungicide prothioconazole.
Huang, J; Jin, F; Li, M; Li, QX; Li, W; Pan, D; Wang, Z; Wu, X, 2022
)
2.38
"Prothioconazole (PTC) is a widely used agricultural fungicide. "( NMR-based metabolomics approach to assess the ecotoxicity of prothioconazole on the earthworm (Eisenia fetida) in soil.
Bao, X; Chen, X; Cui, J; Meng, Z; Wang, J; Xu, W; Yan, Z, 2023
)
2.59
"Prothioconazole (PTC) is a widely used agricultural fungicide, and its parent and metabolite prothioconazole-desthio (dPTC) have been detected in diverse environmental media. "( Intergenerational reproductive toxicity of parental exposure to prothioconazole and its metabolite on offspring and epigenetic regulation associated with DNA methylation in zebrafish.
Diao, J; Huang, S; Jia, M; Li, L; Sun, W; Sun, X; Tian, S; Yan, S; Yue, Y; Zhou, Z; Zhu, W, 2023
)
2.59
"Prothioconazole (PTC) is a broad-spectrum triazole fungicide with one asymmetric center and consists of two enantiomers, "( Enantioselective Toxic Effects of Prothioconazole toward
Tan, C; Xiang, Q; Zhou, Y, 2023
)
2.63
"Prothioconazole (PTC) is a widely used triazolinthione fungicide with low toxicity and short residual period. "( Comparative toxicokinetics and tissue distribution of prothioconazole and prothioconazole-desthio in Chinese lizards (Eremias argus) and transcriptional responses of metabolic-related genes.
Chang, J; Guo, B; Hao, W; Li, J; Li, LYZ; Wang, H; Xie, Y; Xu, P, 2019
)
2.21
"1. Prothioconazole (PTC) is a new type of triazolinthione fungicide used worldwide. "( Toxicokinetics and tissue distribution of prothioconazole in male adult Sprague-Dawley rats following a single oral administration.
Cheng, G; Dai, L; Li, L; Wei, S; Zhou, F, 2015
)
1.3
"Prothioconazole is a broad-spectrum thiocarbamate fungicide."( Approach for Pesticide Residue Analysis for Metabolite Prothioconazole-desthio in Animal Origin Food.
Liu, C; Liu, D; Liu, H; Liu, X; Wang, P; Yao, G; Zhan, J; Zhou, Z, 2017
)
1.42
"Prothioconazole is a new triazolinthione fungicide used in agriculture. "( Prothioconazole and prothioconazole-desthio activities against Candida albicans sterol 14-α-demethylase.
Cools, HJ; Fraaije, BA; Griffiths, WJ; Kelly, DE; Kelly, SL; Lucas, JA; Parker, JE; Rigdova, K; Warrilow, AG, 2013
)
3.28

Effects

ExcerptReferenceRelevance
"Prothioconazole (PTC) has been widely utilized for plant fungal disease control, but its metabolite prothioconazole-desthio (PTC-d) exhibits reproductive toxicity. "( Bioactivity, Uptake, and Distribution of Prothioconazole Loaded on Fluorescent Double-Hollow Shelled Mesoporous Silica in Soybean Plants.
Li, R; Wang, J; Wang, Y; Zhao, Z; Zhu, M, 2023
)
2.62

Toxicity

ExcerptReferenceRelevance
"Triazole fungicides are widely used in agriculture production and have adverse impacts on aquatic organisms."( Toxicity effects in zebrafish embryos (Danio rerio) induced by prothioconazole.
Jia, M; Li, R; Liu, L; Meng, Z; Teng, M; Tian, S; Yan, J; Yan, S; Zhou, Z; Zhu, W, 2019
)
0.75
" In recent years, studies have confirmed that it exerts adverse effects on various species, including aquatic organisms, mammals, and reptiles."( NMR-based metabolomics approach to assess the ecotoxicity of prothioconazole on the earthworm (Eisenia fetida) in soil.
Bao, X; Chen, X; Cui, J; Meng, Z; Wang, J; Xu, W; Yan, Z, 2023
)
1.15
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (5)

ClassDescription
monochlorobenzenesAny member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine.
triazolesAn azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
cyclopropanesCyclopropane and its derivatives formed by substitution.
thiocarbonyl compoundAny compound containing the thiocarbonyl group, C=S.
[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 (16)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency70.97990.007215.758889.3584AID1224835
hypoxia-inducible factor 1 alpha subunitHomo sapiens (human)Potency47.15743.189029.884159.4836AID1224846; AID1224894
RAR-related orphan receptor gammaMus musculus (house mouse)Potency52.47010.006038.004119,952.5996AID1159521; AID1159523
SMAD family member 2Homo sapiens (human)Potency48.96620.173734.304761.8120AID1346924
SMAD family member 3Homo sapiens (human)Potency48.96620.173734.304761.8120AID1346924
GLI family zinc finger 3Homo sapiens (human)Potency45.50110.000714.592883.7951AID1259369; AID1259392
AR proteinHomo sapiens (human)Potency54.48270.000221.22318,912.5098AID1259243; AID1259247
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency68.58960.000657.913322,387.1992AID1259378
progesterone receptorHomo sapiens (human)Potency27.48720.000417.946075.1148AID1346784; AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency64.75280.003041.611522,387.1992AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency34.24320.001530.607315,848.9004AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403
pregnane X nuclear receptorHomo sapiens (human)Potency30.63790.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency64.86010.000229.305416,493.5996AID1259244; AID1259248
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency23.20680.057821.109761.2679AID1159526; AID1159528
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency68.58960.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency68.58960.001551.739315,848.9004AID1259244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1112873Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR2 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112890Selectivity index, ratio of EC50 for Oculimacula acuformis to EC50 for Oculimacula yallundae by germ tube elongation inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112871Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR2 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by germ tube elongation inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
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.
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.
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.
AID1112893Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR2 to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112895Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae MDR to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1413392Antifungal activity against Fusarium graminearum infected in wheat plant assessed as contamination of wheat heads and kernels with deoxynivalenol at 5.5 ml/L (Rvb = 1.2 ppm)2018MedChemComm, Jun-01, Volume: 9, Issue:6
Antifungal amphiphilic kanamycins: new life for an old drug.
AID1112875Fungicidal activity against prochloraz-susceptible Oculimacula yallundae isolate ProS 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.
AID1112887Selectivity index, ratio of EC50 for Oculimacula acuformis to EC50 for Oculimacula yallundae in presence of 10 g glucose by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112885Resistance index, ratio of EC50 for sterol 14alpha-demethylation inhibitor-resistant Oculimacula yallundae TriR1 to EC50 for wild type Oculimacula yallundae TriS by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112894Resistance 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 mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112874Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR1 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112889Fungicidal activity against Oculimacula acuformis assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112892Fungicidal activity against Oculimacula acuformis 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.
AID1112872Resistance index, ratio of EC50 for prochloraz-resistant Oculimacula yallundae isolate ProR1 to EC50 for prochloraz-susceptible Oculimacula yallundae isolate ProS by germ tube elongation inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112876Fungicidal activity against prochloraz-susceptible Oculimacula yallundae isolate ProS assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks2013Pest 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.
AID1112888Fungicidal activity against Oculimacula yallundae assessed as inhibition of mycelial growth in presence of 10 g glucose incubated at 19 degC in dark for 4 weeks2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
AID1112882Resistance 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 mycelial growth inhibition assay2013Pest management science, Jan, Volume: 69, Issue:1
Fungicide resistance status in French populations of the wheat eyespot fungi Oculimacula acuformis and Oculimacula yallundae.
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.
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.
AID1413391Antifungal activity against Fusarium graminearum infected in wheat plant assessed as contamination of wheat heads and kernels with deoxynivalenol at 2.8 ml/L (Rvb = 1.2 ppm)2018MedChemComm, Jun-01, Volume: 9, Issue:6
Antifungal amphiphilic kanamycins: new life for an old drug.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (78)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (1.28)29.6817
2010's35 (44.87)24.3611
2020's42 (53.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 39.20

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index39.20 (24.57)
Research Supply Index4.37 (2.92)
Research Growth Index5.98 (4.65)
Search Engine Demand Index84.49 (26.88)
Search Engine Supply Index3.17 (0.95)

This Compound (39.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.56%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other76 (97.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]