Page last updated: 2024-11-12

cyantraniliprole

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

Description

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

cyantraniliprole : A carboxamide that is chlorantraniliprole in which the chlorine atom attached to the phenyl ring has been replaced by a cyano group. A ryanodine receptor agonist, it is used as insecticide for the control of whitefly, thrips, aphids, fruitflies, and fruit worms in crops such as onions, potatoes and tomatoes. It is highly toxic to honeybees. [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 CID11578610
CHEMBL ID2286761
CHEBI ID132300
SCHEMBL ID166640
MeSH IDM0557719

Synonyms (43)

Synonym
3-bromo-1-(3-chloropyridin-2-yl)-n-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-1h-pyrazole-5-carboxamide
cyantraniliprole
3-bromo-1-(3-chloro-2-pyridyl)-4'-cyano-2'-methyl-6'-(methylcarbamoyl)pyrazole-5-carboxanilide
3-bromo-1-(3-chloro-2-pyridinyl)-n-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-1h-pyrazole-5-carboxamide
zyrox
CHEBI:132300
736994-63-1
lo6k6h48fd ,
unii-lo6k6h48fd
cyantraniliprole [iso]
1h-pyrazole-5-carboxamide, 3-bromo-1-(3-chloro-2-pyridinyl)-n-(4-cyano-2-methyl-6-((methylamino)carbonyl)phenyl)-
3-bromo-1-(3-chloro-2-pyridinyl)-n-(4-cyano-2-methyl-6-((methylamino)carbonyl)phenyl)-1h-pyrazole-5-carboxamide
dpx-hgw 86
cyazypyr
SCHEMBL166640
CHEMBL2286761
syn-545377
3-bromo-1-(3-chloropyridin-2-yl)-n-(4-cyano-2-methyl-6-(n-methylcarbamoyl)phenyl)-1h-pyrazole-5-carboxamide
exirel (insecticide)
1372152-11-8
benevia
cyantraniliprole [mi]
DTXSID2058174
DVBUIBGJRQBEDP-UHFFFAOYSA-N
3-bromo-1-(3-chloro-2-pyridinyl)-n-[4-cyano-2-methyl-6-[(methylamino)-carbonyl]phenyl]-1h-pyrazole-5-carboxamide
HY-12779
AKOS027322013
cyantraniliprole, pestanal(r), analytical standard
mfcd28053506
bdbm50488570
NCGC00485938-01
5-bromo-2-(3-chloropyridin-2-yl)-n-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]pyrazole-3-carboxamide
BCP24173
EX-A1458
Q17073330
N10852
1h-pyrazole-5-carboxamide,3-bromo-1-(3-chloro-2-pyridinyl)-n-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-
1ST20489
MS-28788
1h-pyrazole-5-carboxamide, 3-bromo-1-(3-chloro-2-pyridinyl)-n-[4-cyano-2-methyl-6-[(methylamino)carbonyl]phenyl]-
EN300-7492747
3-bromo-1-(3-chloropyridin-2-yl)-n-(4-cyano-2-methyl-6-(methylcarbamoyl)phenyl)-1h-pyrazole-5-carboxamide
Z3244811253

Research Excerpts

Overview

Cyantraniliprole is a synthetic insecticide used to control pests of up to 23 different types of crops. It acts on a broad spectrum of insect pests, exclusively by activating their ryanodine receptors.

ExcerptReferenceRelevance
"Cyantraniliprole is a synthetic insecticide used to control pests of up to 23 different types of crops. "( Cyantraniliprole impairs reproductive parameters by inducing oxidative stress in adult female wistar rats.
Beu, CCL; da Silva Scarton, SR; Dos Santos, AC; Dos Santos, DP; Fernades, GSA; Guerra, MT; Guimarães, ATB; Simão, ANC; Tsuzuki, F, 2022
)
3.61
"Cyantraniliprole is a novel diamide insecticide that acts upon the ryanodine receptor (RyR) and has broad application prospects. "( Transcriptomics and enzymology combined five gene expressions to reveal the responses of earthworms (Eisenia fetida) to the long-term exposure of cyantraniliprole in soil.
Du, Q; Jiang, X; Li, X; Liu, X; Qiao, Z; Yao, X; Zhang, F; Zhang, J, 2021
)
2.26
"Cyantraniliprole is a novel anthranilic diamide insecticide that acts on a broad spectrum of insect pests, exclusively by activating their ryanodine receptors. "( Baseline susceptibility of Mediterranean strains of Trialeurodes vaporariorum (Westwood) to cyantraniliprole.
Belando, A; Bielza, P; Grávalos, C; Moreno, I, 2018
)
2.14
"Cyantraniliprole is an anthranilic diamide insecticide, belonging to the ryanoid class, with a broad range of applications against several pests. "( Magnitude of cyantraniliprole residues in tomato following open field application: pre-harvest interval determination and risk assessment.
Kasiotis, KM; Malhat, F; Shalaby, S, 2018
)
2.29
"Cyantraniliprole is a second-generation diamide insecticide that exhibited excellent biological efficacy against a variety of pests. "( Growth, DNA damage and biochemical toxicity of cyantraniliprole in earthworms (Eisenia fetida).
Jiang, X; Li, X; Qiao, Z; Sun, S; Yao, X; Yu, H; Zhang, F; Zhang, J, 2019
)
2.21
"Cyantraniliprole is a novel insecticide for control of multiple chewing and sucking insect pest species including the sweetpotato whitefly Bemisia tabaci (Gennadius), which is one of the most important polyphagous pests in tropical, subtropical, and Mediterranean regions. "( An EPG study of the probing behavior of adult Bemisia tabaci biotype Q (Hemiptera: Aleyrodidae) following exposure to cyantraniliprole.
Alvarez, JM; Annan, IB; Bassi, A; Cassanelli, S; Chicca, M; Civolani, S; Fano, EA; Giorgini, M; Parrella, G; Rison, JL, 2014
)
2.05

Treatment

ExcerptReferenceRelevance
"Cyantraniliprole-treated females of the mated pairs with the lower dose laid more eggs."( Lethal and sublethal effects of cyantraniliprole on Bactrocera dorsalis (Hendel) (Diptera: Tephritidae).
Chen, J; He, S; Jang, EB; Zhang, R, 2015
)
1.42

Toxicity

ExcerptReferenceRelevance
"Cyantraniliprole, the second generation of diamide insecticides, is widely used to control various pests, which will certainly result in adverse effects on earthworms in soil."( Effect of different exposure times and doses of cyantraniliprole on oxidative stress and genotoxicity in earthworms (Eisenia fetida).
Li, Z; Liu, C; Liu, D; Wang, J; Xia, X; Xue, Y, 2023
)
2.61

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" An increased dosage of cyantraniliprole did not influence on its translocation in plant tissues, however, it influenced on the present amount of active ingredient."( Translocation of chlorantraniliprole and cyantraniliprole applied to corn as seed treatment and foliar spraying to control Spodoptera frugiperda (Lepidoptera: Noctuidae).
Carús Guedes, JV; Melo, AA; Perini, CR; Pes, MP; Silva, FMA; Stacke, RS; Zanella, R, 2020
)
1.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
ryanodine receptor agonistA ryanodine receptor modulator which activates the receptor. Ryanodine receptors (RyRs) act as selective ion channels, modulating the release of calcium. Activating the receptors causes the release of calcium, so depleting internal calcium and ultimately preventing further muscle contraction.
[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 (6)

ClassDescription
pyrazole insecticide
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.
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
organobromine compoundA compound containing at least one carbon-bromine bond.
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
secondary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1).
[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 (20)

Assay IDTitleYearJournalArticle
AID1111785Insecticidal activity against adult Dendroctonus ponderosae assessed as mortality after 12 hr by filter paper assay2011Pest management science, May, Volume: 67, Issue:5
Laboratory assays of select candidate insecticides for control of Dendroctonus ponderosae.
AID1111784Insecticidal activity against adult Dendroctonus ponderosae assessed as mortality after 24 hr by filter paper assay2011Pest management science, May, Volume: 67, Issue:5
Laboratory assays of select candidate insecticides for control of Dendroctonus ponderosae.
AID1112581Insecticidal activity against Myzus persicae (green peach aphid) assessed as mortality by greenhouse assay2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Novel diamide insecticides: sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives.
AID1111782Insecticidal activity against adult Dendroctonus ponderosae assessed as mortality applied topically to ventral surface of insect mesothorax after 24 hr2011Pest management science, May, Volume: 67, Issue:5
Laboratory assays of select candidate insecticides for control of Dendroctonus ponderosae.
AID1111783Insecticidal activity against adult Dendroctonus ponderosae assessed as mortality applied topically on the ventral surface of insect mesothorax after 12 hr2011Pest management science, May, Volume: 67, Issue:5
Laboratory assays of select candidate insecticides for control of Dendroctonus ponderosae.
AID1111781Insecticidal activity against adult female Dendroctonus ponderosae assessed as mortality after 24 hr by filter paper assay2011Pest management science, May, Volume: 67, Issue:5
Laboratory assays of select candidate insecticides for control of Dendroctonus ponderosae.
AID1111779Insecticidal activity against adult female Dendroctonus ponderosae assessed as mortality applied topically to ventral surface of insect mesothorax after 24 hr2011Pest management science, May, Volume: 67, Issue:5
Laboratory assays of select candidate insecticides for control of Dendroctonus ponderosae.
AID1112582Insecticidal activity against Plutella xylostella (diamondback moth) assessed as mortality by greenhouse assay2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Novel diamide insecticides: sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives.
AID1111778Insecticidal activity against adult male Dendroctonus ponderosae assessed as mortality applied topically to ventral surface of insect mesothorax after 24 hr2011Pest management science, May, Volume: 67, Issue:5
Laboratory assays of select candidate insecticides for control of Dendroctonus ponderosae.
AID1111780Insecticidal activity against adult male Dendroctonus ponderosae assessed as mortality after 24 hr by filter paper assay2011Pest management science, May, Volume: 67, Issue:5
Laboratory assays of select candidate insecticides for control of Dendroctonus ponderosae.
AID1112590Aqueous solubility of the compound at pH 72012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Novel diamide insecticides: sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives.
AID1112591Displacement of [3H]-Tritium-N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide from Myzus persicae (green peach aphid) ryanodine receptor2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Novel diamide insecticides: sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives.
AID1112592Displacement of [3H]-Tritium-N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide from Spodoptera littoralis ryanodine receptor2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Novel diamide insecticides: sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives.
AID1112589Lipophilicity, log P of the compound2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Novel diamide insecticides: sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives.
AID1112583Insecticidal activity against Spodoptera littoralis assessed as mortality by greenhouse assay2012Bioorganic & medicinal chemistry letters, Jun-01, Volume: 22, Issue:11
Novel diamide insecticides: sulfoximines, sulfonimidamides and other new sulfonimidoyl derivatives.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (107)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's59 (55.14)24.3611
2020's48 (44.86)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 40.58

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

MetricThis Compound (vs All)
Research Demand Index40.58 (24.57)
Research Supply Index4.70 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index97.71 (26.88)
Search Engine Supply Index3.27 (0.95)

This Compound (40.58)

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%
Other109 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]