Compounds > cyenopyrafen
Page last updated: 2024-11-12

cyenopyrafen

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

Description

cyenopyrafen: an acaricide; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cyenopyrafen : A member of the class of pyrazoles that is ethene in which the hydrogens at position 1 have been replaced by p-tert-butylphenyl and cyano groups, while the hydrogens at position 2 have been replaced by pivaloyloxy and 1,3,4-trimethylpyrazol-5-yl groups (the E isomer). A proacaricide (by hydrolysis of the pivalate ester linkage to give the corresponding enol), it was formerly used for the control of mites in fruit, vegetables and tea. [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 CID18772482
CHEMBL ID2287243
CHEBI ID81820
SCHEMBL ID728428
SCHEMBL ID26300
MeSH IDM000598401

Synonyms (27)

Synonym
unii-1s67w8bou3
cyenopyrafen [iso]
1s67w8bou3 ,
C18545
560121-52-0
cyenopyrafen
SCHEMBL728428
SCHEMBL26300
chebi:81820 ,
CHEMBL2287243
propanoic acid, 2,2-dimethyl-, (1e)-2-cyano-2-(4-(1,1-dimethylethyl)phenyl)-1-(1,3,4-trimethyl-1h-pyrazol-5-yl)ethenyl ester
nc-512
(1e)-2-cyano-2-[4-(1,1-dimethylethyl)phenyl]-1-(1,3,4-trimethyl-1h-pyrazol-5-yl)ethenyl 2,2-dimethylpropanoate
cyenopyrafene
(e)-2-(4-tert-butylphenyl)-2-cyano-1-(1,3,4-trimethyl-1h-pyrazol-5-yl)vinyl pivalate
(1e)-2-(4-tert-butylphenyl)-2-cyano-1-(1,3,4-trimethyl-1h-pyrazol-5-yl)ethenyl 2,2-dimethylpropanoate
(e)-2-(4-tert-butylphenyl)-2-cyano-1-(1,3,4-trimethylpyrazol-5-yl)vinyl 2,2-dimethylpropionate
DTXSID7058127
(2e)-3-(2,2-dimethylpropanoyloxy)-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl) acrylonitrile
(2e)-3-(2,2-dimethylpropanoyloxy)-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl)acrylonitrile
APJLTUBHYCOZJI-VZCXRCSSSA-N
cyenopyrafen 100 microg/ml in acetonitrile
Q27155617
2-(4-(tert-butyl)phenyl)-2-cyano-1-(1,3,4-trimethyl-1h-pyrazol-5-yl)vinyl pivalate
(e)-2-(4-(tert-butyl)phenyl)-2-cyano-1-(1,3,4-trimethyl-1h-pyrazol-5-yl)vinyl pivalate
268743-66-4
[(e)-2-(4-tert-butylphenyl)-2-cyano-1-(2,4,5-trimethylpyrazol-3-yl)ethenyl] 2,2-dimethylpropanoate

Research Excerpts

Overview

Cyenopyrafen is a Mitochondrial Electron Transport Inhibitor (METI) acaricide with a novel mode of action at complex II. Recently developed for the control of the spider mite Tetranychus urticae.

ExcerptReferenceRelevance
"Cyenopyrafen is an inhibitor of complex II of the mitochondrial electron transport chain. "( Cross-resistance between cyenopyrafen and pyridaben in the twospotted spider mite Tetranychus urticae (Acari: Tetranychidae).
Osakabe, M; Sugimoto, N, 2014)		2.15
"Cyenopyrafen is a recently developed acaricide with a new mode of action as a complex II inhibitor. "( Molecular analysis of cyenopyrafen resistance in the two-spotted spider mite Tetranychus urticae.
Bajda, S; Dermauw, W; Khalighi, M; Osakabe, M; Tirry, L; Van Leeuwen, T; Wybouw, N, 2016)		2.19
"Cyenopyrafen is a Mitochondrial Electron Transport Inhibitor (METI) acaricide with a novel mode of action at complex II, which has been recently developed for the control of the spider mite Tetranychus urticae, a pest of eminent importance globally. "( Functional characterization of the Tetranychus urticae CYP392A11, a cytochrome P450 that hydroxylates the METI acaricides cyenopyrafen and fenpyroximate.
Douris, V; Morou, E; Myridakis, A; Nauen, R; Riga, M; Stephanou, EG; Tsakireli, D; Van Leeuwen, T; Vontas, J, 2015)		2.07
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
proacaricideA compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active insecticide for which it is a proacaricide.
agrochemicalAn agrochemical is a substance that is used in agriculture or horticulture.
[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 (3)

ClassDescription
nitrileA compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it.
pivalate esterA carboxylic ester of pivalic acid.
pyrazoles
[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]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1111788Resistance ratio, LC50 for adult Panonychus ulmi HS to LC50 for adult Panonychus ulmi PSR TK2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID1111794Insecticidal activity against Panonychus ulmi HS in plum tree leaf assessed as mortality at adult stage compound treated by spray application measured after 7 to 8 days treatment2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
AID1111791Insecticidal activity against Panonychus ulmi PSR-TK in plum tree leaf assessed as mortality at adult stage compound treated by spray application measured after 7 to 8 days treatment2011Pest management science, Oct, Volume: 67, Issue:10
Monitoring of spirodiclofen susceptibility in field populations of European red mites, Panonychus ulmi (Koch) (Acari: Tetranychidae), and the cross-resistance pattern of a laboratory-selected strain.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (60.00)24.3611
2020's4 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.58

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 Index29.58 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index51.30 (26.88)
Search Engine Supply Index3.26 (0.95)

This Compound (29.58)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		2.2110amino-acid anion
acrylonitrile
[no description available]		3.6780aliphatic nitrile;
volatile organic compound		antifungal agent;
carcinogenic agent;
fungal metabolite;
mutagen;
polar aprotic solvent
hydrazine
diamine : Any polyamine that contains two amino groups.		2.2110azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
clofentezine
clofentezine: acaricide, primarily a mite ovicide; structure given in first source. clofentezine : A tetrazine that is 1,2,4,5-tetrazine in which both of the hydrogens have been replaced by o-chlorophenyl groups.		2.0610monochlorobenzenes;
organochlorine acaricide;
tetrazine		mite growth regulator;
tetrazine acaricide
4-chloro-n-((4-(1,1-dimethylethyl)phenyl)methyl)-3-ethyl-1-methyl-1h-pyrazole-5-carboxamide
[no description available]		2.0610pyrazole acaricide;
pyrazole insecticide		mitochondrial NADH:ubiquinone reductase inhibitor
pyridaben
[no description available]		7.5220organochlorine acaricide;
organochlorine insecticide;
pyridazinone		mitochondrial NADH:ubiquinone reductase inhibitor
acequinocyl
acequinocyl: structure in first source. acequinocyl : An acetate ester consisting of 1,4-naphthoquinone bearing acetoxy and dodecyl substituents at positions 2 and 3 respectively.		2.06101,4-naphthoquinones;
acetate ester		acaricide;
mitochondrial cytochrome-bc1 complex inhibitor
borneo
Borneo: An island in the Malay Archipelago, east of Sumatra, north of Java, and west of Celebes. It is the third largest island in the world. Its name is a Portuguese alteration of BRUNEI, located on it. (From Webster's New Geographical Dictionary, 1988, p163; Room, Brewer's Dictionary of Names, 1992, p73)		2.0610organofluorine acaricide
bifenazate
bifenazate: an acaricide. bifenazate : A carboxylic ester obtained by formal condensation of 2-(4-methoxy[1,1'-biphenyl]-3-yl)hydrazinecarboxylic acid with 2-propanol.		7.5220carboxylic esteracaricide
spirodiclofen
spirodiclofen: an acaricide		2.0610dichlorobenzene;
gamma-lactone;
organochlorine acaricide;
oxaspiro compound
fenpyroximate
fenpyroximate: structure in first source		7.1110pyrazole acaricide;
tert-butyl ester		mitochondrial NADH:ubiquinone reductase inhibitor
spiromesifen
spiromesifen: insecticide; structure in first source. spiromesifen : A butenolide that is but-2-en-4-olide bearing a 2,4,6-trimethylphenyl group at position 3, a 3,3-dimethylbutyryloxy group at position 4 and a spiro-fused cyclopentyl ring at position 5.		2.0610butenolideinsecticide
medigoxin
spirotetramat: for the control of a broad spectrum of sucking insects; structure in first source. spirotetramat : An azaspiro compound that is methoxycyclohexane which is fused at position 4 to the 5-position of a 1,5-dihydro-2H-pyrrol-2-one that is substituted at positions 3 and 4 by 2,5-dimethylphenyl and (ethoxycarbonyl)oxy groups, respectively (the cis isomer). It is a proinsecticide (via hydrolysis of the ethyl carbonate group to give the corresponding 4-hydroxypyrrol-2-one, "spirotetramat-enol") and is used for the control of a wide range of sucking insects on fruit and potato crops.		2.0610
cyflumetofen
cyflumetofen: acaricide; structure in first source. cyflumetofen : A racemate comprising equimolar amounts of (R)- and (S)-cyflumetofen. A proacaricide (via ester hydrolysis and subsequent decarboxylation), it is used to control phytophagous mites at all development stages in a variety of fruit crops. It acts as an inhibitor of complex II of mitochondrial electron transport chain.. 2-methoxyethyl 2-(4-tert-butylphenyl)-2-cyano-3-oxo-3-[2-(trifluoromethyl)phenyl]propanoate : A nitrile that is acetonitrile in which the methyl hydrogens have been replaced by o-trifluoromethylbenzoyl, p-tert-butylphenyl, and (2-methoxyethoxy)carbonyl groups.		3.3150(trifluoromethyl)benzenes;
2-methoxyethyl ester;
beta-ketoester;
nitrile
ConditionIndicatedRelationship StrengthStudiesTrials