Page last updated: 2024-11-06

bupirimate

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

Description

Bupirimate is a fungicide used to control powdery mildew diseases in various crops, including grapes, apples, and cucumbers. It acts as a systemic fungicide, meaning it is absorbed by the plant and translocated throughout its tissues. Bupirimate inhibits the biosynthesis of ergosterol, an essential component of fungal cell membranes, leading to cell death. The compound was first synthesized in the 1970s and has been widely used in agriculture since then. Bupirimate is effective in controlling powdery mildew in both preventive and curative applications. It is also known for its long-lasting activity, providing protection for extended periods. Due to its efficacy and broad-spectrum activity, bupirimate remains an important fungicide in crop protection. However, concerns have been raised about its potential environmental impact, particularly regarding its persistence in soil and its potential to accumulate in aquatic organisms. Research on bupirimate focuses on developing alternative fungicides with reduced environmental risks, as well as exploring new applications and optimizing its use in crop protection.'

bupirimate : A member of the class of aminopyrimidines that is 2-ethylaminopyrimidine carrying methyl, butyl and dimethylaminosulfooxy substituents at posiitons 4, 5 and 6 respectively. [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 CID38884
CHEMBL ID3183902
CHEBI ID81952
SCHEMBL ID22961
MeSH IDM0194649

Synonyms (45)

Synonym
pp588
dimethylsulfamic acid 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl ester
nanogen index code bpt (1-011)
bupirimate [ansi:bsi:iso]
5-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulphamate
5-butyl-2-ethylamino-6-methylpyrimidin-4-yldimethylsulphamate
bupirimate
2-aethylamino-5-butyl-4-yl-dimethylsulfamat [german]
sulfamic acid, n,n-dimethyl-, ester with 5-butyl-2-ethylamino-6-methylpyrimidin-4-ol
5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl dimethylsulfamate
nimrod
brn 0758056
einecs 255-391-2
sulfamic acid, dimethyl-, 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl ester
41483-43-6
2-aminoethyl-5-butyl-4(n)-methylsulfonate-6-methylpyrimidine
[5-butyl-2-(ethylamino)-6-methylpyrimidin-4-yl] n,n-dimethylsulfamate
C18776
NCGC00255539-01
dtxcid4021688
dtxsid6041688 ,
cas-41483-43-6
tox21_301427
unii-mcj121rioi
mcj121rioi ,
2-aethylamino-5-butyl-4-yl-dimethylsulfamat
SCHEMBL22961
pp-588
bupirimate [mi]
n,n-dimethylsulfamic acid 5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl ester
bupirimate [iso]
5-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulfamate
5-butyl-2-(ethylamino)-6-methylpyrimidin-4-yl dimethylsulfamate
CHEBI:81952 ,
buprimate
DSKJPMWIHSOYEA-UHFFFAOYSA-N
5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl dimethylsulfamate #
CHEMBL3183902
bupirimate, pestanal(r), analytical standard
AKOS030242088
bupirimate 100 microg/ml in acetonitrile
58694-46-5
Q2928285
AMY8988
n,n-dimethyl-, 5-butyl-2-(ethylamino)-6-methyl-4-sulfamic acid

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The purpose of this retrospective study was to determine whether epidural fentanyl-bupivacaine patient-controlled analgesia (PCA) was more efficacious and had fewer adverse effects than epidural or intravenous morphine PCA."( Efficacy and adverse effects of patient-controlled epidural or intravenous analgesia after major surgery.
Hu, JS; Liew, C; Lui, PW; Teng, YH; Tsai, SK, 2004
)
0.32
" Adverse effects including nausea, vomiting, pruritus, urinary retention, sedation, motor block, and respiratory depression (< 8 breaths per minute) were recorded."( Efficacy and adverse effects of patient-controlled epidural or intravenous analgesia after major surgery.
Hu, JS; Liew, C; Lui, PW; Teng, YH; Tsai, SK, 2004
)
0.32
" There were no differences in other adverse events such as urinary retention, sedation, and motor block among the three groups."( Efficacy and adverse effects of patient-controlled epidural or intravenous analgesia after major surgery.
Hu, JS; Liew, C; Lui, PW; Teng, YH; Tsai, SK, 2004
)
0.32
" It is considered safe to use continuous epidural PCA with fentanyl-bupivacaine in patients receiving major elective surgery."( Efficacy and adverse effects of patient-controlled epidural or intravenous analgesia after major surgery.
Hu, JS; Liew, C; Lui, PW; Teng, YH; Tsai, SK, 2004
)
0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
androgen antagonistA compound which inhibits or antagonises the biosynthesis or actions of androgens.
antifungal agrochemicalAny substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties.
[role 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]

Drug Classes (4)

ClassDescription
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
sulfamate ester
aminopyrimidineA member of the class of pyrimidines that is pyrimidine substituted by at least one amino group and its derivatives.
pyrimidine fungicideAny pyrimidine antifungal agent that has been used as a fungicide.
[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 (17)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency70.97990.002541.796015,848.9004AID1347398
RAR-related orphan receptor gammaMus musculus (house mouse)Potency30.63790.006038.004119,952.5996AID1159521; AID1159523
GLI family zinc finger 3Homo sapiens (human)Potency61.13060.000714.592883.7951AID1259369; AID1259392
AR proteinHomo sapiens (human)Potency37.49290.000221.22318,912.5098AID1259243; AID1259247; AID743035; AID743042; AID743053; AID743054; AID743063
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency20.66080.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency27.30600.000417.946075.1148AID1346795
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency27.53570.000214.376460.0339AID720692
retinoid X nuclear receptor alphaHomo sapiens (human)Potency48.96620.000817.505159.3239AID1159531
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency37.77670.001530.607315,848.9004AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403
pregnane X nuclear receptorHomo sapiens (human)Potency9.68850.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency37.45300.000229.305416,493.5996AID1259244; AID1259248; AID743069; AID743075; AID743080; AID743091
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency43.64120.001019.414170.9645AID743191
aryl hydrocarbon receptorHomo sapiens (human)Potency16.40340.000723.06741,258.9301AID743085; AID743122
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency54.48270.000323.4451159.6830AID743065; AID743067
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency30.84110.000627.21521,122.0200AID743202; AID743219
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency27.30600.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency27.30600.001551.739315,848.9004AID1259244
[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]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (11.11)18.7374
1990's3 (33.33)18.2507
2000's2 (22.22)29.6817
2010's1 (11.11)24.3611
2020's2 (22.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.06

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 Index41.06 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.11 (4.65)
Search Engine Demand Index59.14 (26.88)
Search Engine Supply Index2.17 (0.95)

This Compound (41.06)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (10.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (10.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]