Page last updated: 2024-11-12

flupyradifurone

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

Description

flupyradifurone: has insecticidal activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

flupyradifurone : A tertiary amino compound that is ammonia in which the nitrogens have been replaced by (6-chloropyridin-3-yl)methyl, 2,2-difluoroethyl, and 5-oxo-2,5-dihydrofuran-3-yl groups, respectively. A nicotinic acetylcholine receptor (AChR) agonist, it is used as an insecticide to control sucking pests in a variety of crops. [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 CID16752772
CHEMBL ID5206787
CHEBI ID133997
SCHEMBL ID123283

Synonyms (35)

Synonym
951659-40-8
CHEBI:133997
4-[[(6-chloro-3-pyridinyl)methyl](2,2-difluoroethyl)amino]-2(5h)-furanone
flupyradifuron
4-[(6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino]furan-2(5h)-one
4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5h)-one
flupyradifurone
sivanto
8h7jt159d0 ,
flupyradifurone [iso]
unii-8h7jt159d0
4-(((6-chloropyridin-3-yl)methyl)(2,2-difluoroethyl)amino)furan-2(5h)-one
byi-02960
2(5h)-furanone, 4-(((6-chloro-3-pyridinyl)methyl)(2,2-difluoroethyl)amino)-
SCHEMBL123283
4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5h)-one
4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5h)one
4[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5h)-one
4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5h)-one
4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan- 2(5h)-one
DTXSID10872811
flupyradifurone, pestanal(r), analytical standard
3-[(6-chloropyridin-3-yl)methyl-(2,2-difluoroethyl)amino]-2h-furan-5-one
Q21050747
3-[2,2-bis(fluoranyl)ethyl-[(6-chloranylpyridin-3-yl)methyl]amino]-2~{h}-furan-5-one
A901267
AT26716
MS-24124
2(5h)-furanone, 4-[[(6-chloro-3-pyridinyl)methyl](2,2-difluoroethyl)amino]-; 3-[[(6-chloro-3-pyridyl)methyl](2,2-difluoroethyl)amino]-2h-furan-5-one; 4-[[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino]furan-2(5h)-one; byi 02960; flupyradifurone
HY-145295
4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-2,5-dihydrofuran-2-one
CS-0370911
2(5h)-furanone, 4-[[(6-chloro-3-pyridinyl)methyl](2,2-difluoroethyl)amino]-
Z3664682052
CHEMBL5206787

Research Excerpts

Overview

Flupyradifurone is a novel neonicotinoid insecticide, mainly used in okra in subtropical conditions for controlling whitefly and jassids. It is thought to be relatively 'bee safe' but can be present in the nectar and pollen of bee-attractive crops.

ExcerptReferenceRelevance
"Flupyradifurone is a novel systemic insecticide that is thought to be relatively 'bee safe' although it can be present in the nectar and pollen of bee-attractive crops."( Exposure to the novel insecticide flupyradifurone impairs bumblebee feeding motivation, learning, and memory retention.
Muth, F; Siviter, H, 2022
)
1.72
"Flupyradifurone (FPF) is a novel neonicotinoid insecticide that is replacing traditional neonicotinoids over a large geographical range to control pests."( Exposure to flupyradifurone affect health of biocontrol parasitoid Binodoxys communis (Hymenoptera: Braconidae) via disrupting detoxification metabolism and lipid synthesis.
Cui, J; Gao, X; Ji, J; Li, D; Luo, J; Niu, L; Wang, L; Zhang, K; Zhao, L; Zhu, X, 2023
)
2.01
"Flupyradifurone is a novel insecticide against sucking pests."( Characterization of flupyradifurone resistance in the whitefly Bemisia tabaci Mediterranean (Q biotype).
Che, W; Feng, H; Luo, C; Wang, J; Wang, R; Zhang, J, 2020
)
1.6
"Flupyradifurone is a novel neonicotinoid insecticide, mainly used in okra in subtropical conditions for controlling whitefly and jassids. "( Effect of Organic Amendment on Mobility Behavior of Flupyradifurone in Two Different Indian Soils.
Mukherjee, I; Sarkar, S, 2021
)
2.31
"Flupyradifurone is shown to be an extremely useful, fast-acting, new chemical tool in integrated crop management offering simultaneous control of whiteflies and strong suppression of viral infections via its rapid knockdown action and good residual activity. "( Flupyradifurone effectively manages whitefly Bemisia tabaci MED (Hemiptera: Aleyrodidae) and tomato yellow leaf curl virus in tomato.
Achimastou, A; Grispou, M; Nauen, R; Roditakis, E; Stavrakaki, M; Tsagkarakou, A; Van Waetermeulen, X, 2017
)
3.34
"Flupyradifurone is a member of a novel class of insecticides that possess excellent insecticidal activities. "( Design, synthesis, and insecticidal activity evaluation of novel 4-(N, N-diarylmethylamines)furan-2(5H)-one derivatives as potential acetylcholine receptor insecticides.
Chen, J; He, W; Liu, D; Liu, Z; Qi, P; Shi, J; Song, B; Tian, P, 2019
)
1.96
"Flupyradifurone is a novel butenolide pesticide; its toxicity on A."( Toxicity and Sublethal Effects of Flupyradifurone, a Novel Butenolide Insecticide, on the Development and Fecundity of Aphis gossypii (Hemiptera: Aphididae).
Chen, XW; Chi, H; Gao, XW; Liang, PZ; Ma, KS; Tang, CY; Xia, J, 2019
)
1.51
"Flupyradifurone (Sivanto) is a novel systemic insecticide from the butenolide class developed by Bayer. "( An Evaluation of the Honey Bee (Hymenoptera: Apidae) Safety Profile of a New Systemic Insecticide, Flupyradifurone, Under Field Conditions in Florida.
Cabrera, AR; Campbell, JW; Ellis, JD; Stanley-Stahr, C, 2016
)
2.09

Effects

ExcerptReferenceRelevance
"Flupyradifurone has been marketed as an alternative to non-fluorinated neonicotinoids."( Synthesis, molecular docking studies, and larvicidal activity evaluation of new fluorinated neonicotinoids against Anopheles darlingi larvae.
Bezdudnyy, A; da Silva Mesquita, R; Grafov, A; Grafova, I; Kliukovskyi, D; Kyrylchuk, A; Leskelä, M; Rozhenko, A; Tadei, WP, 2020
)
1.28

Treatment

ExcerptReferenceRelevance
"Flupyradifurone-treated bees were also less motivated to feed."( Exposure to the novel insecticide flupyradifurone impairs bumblebee feeding motivation, learning, and memory retention.
Muth, F; Siviter, H, 2022
)
1.72

Toxicity

Flupyradifurone was shown in acute toxicity tests to be several orders of magnitude less toxic to western honey bee. Within the conditions set forth by our experimental design, our collective data suggest no adverse effects on honey bee colonies when following label directions.

ExcerptReferenceRelevance
"An effective analytical method for the simultaneous determination of a novel insecticide flupyradifurone and its two metabolites was developed using ultra high performance liquid chromatography with tandem mass spectrometry coupled with a quick, easy, cheap, effective, rugged, and safe procedure."( Simultaneous determination of flupyradifurone and its two metabolites in fruits, vegetables, and grains by a modified quick, easy, cheap, effective, rugged, and safe method using ultra high performance liquid chromatography with tandem mass spectrometry.
Dong, F; Li, Y; Liu, X; Wu, X; Xu, J; Zheng, Y, 2016
)
0.94
" Within the conditions set forth by our experimental design, our collective data suggest no adverse effects of flupyradifurone on honey bee colonies when following label directions."( An Evaluation of the Honey Bee (Hymenoptera: Apidae) Safety Profile of a New Systemic Insecticide, Flupyradifurone, Under Field Conditions in Florida.
Cabrera, AR; Campbell, JW; Ellis, JD; Stanley-Stahr, C, 2016
)
0.86

Bioavailability

ExcerptReferenceRelevance
" Such activity is connected to a unique binding pattern of the synthesized compounds to insect's nAChR and to their enhanced bioavailability owing to introduction of fluorinated amino-moieties."( Synthesis, molecular docking studies, and larvicidal activity evaluation of new fluorinated neonicotinoids against Anopheles darlingi larvae.
Bezdudnyy, A; da Silva Mesquita, R; Grafov, A; Grafova, I; Kliukovskyi, D; Kyrylchuk, A; Leskelä, M; Rozhenko, A; Tadei, WP, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
nicotinic acetylcholine receptor agonistAn agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
insecticideStrictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
[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 (5)

ClassDescription
butenolideA gamma-lactone that consists of a 2-furanone skeleton and its substituted derivatives.
monochloropyridineA chloropyridine in which only one chlorine is attached to the pyridine ring.
organofluorine insecticide
enamineAn amine RNR'R'' where R has a double bond adjacent to the amine nitrogen.
tertiary amino compoundA compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
[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 (5)

Assay IDTitleYearJournalArticle
AID1850564Toxicity in Aphis craccivora assessed as mortality at 100 mg/ml relative to control2022Bioorganic & medicinal chemistry, 08-01, Volume: 67Synthesis and medicinal chemistry of tetronamides: Promising agrochemicals and antitumoral compounds.
AID1850565Toxicity in Nilaparvata lugens assessed as mortality at 100 mg/ml relative to control2022Bioorganic & medicinal chemistry, 08-01, Volume: 67Synthesis and medicinal chemistry of tetronamides: Promising agrochemicals and antitumoral compounds.
AID1850567Toxicity in Myzus persicae assessed as mortality at 0.80 mg/L relative to control2022Bioorganic & medicinal chemistry, 08-01, Volume: 67Synthesis and medicinal chemistry of tetronamides: Promising agrochemicals and antitumoral compounds.
AID1850566Toxicity in Anopheles darlingi larvae measured after 48 hrs2022Bioorganic & medicinal chemistry, 08-01, Volume: 67Synthesis and medicinal chemistry of tetronamides: Promising agrochemicals and antitumoral compounds.
AID1850568Toxicity in Aphis gossypii assessed as mortality at 4 mg/L relative to control2022Bioorganic & medicinal chemistry, 08-01, Volume: 67Synthesis and medicinal chemistry of tetronamides: Promising agrochemicals and antitumoral compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (64)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's21 (32.81)24.3611
2020's43 (67.19)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.93

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 Index35.93 (24.57)
Research Supply Index4.19 (2.92)
Research Growth Index4.85 (4.65)
Search Engine Demand Index89.85 (26.88)
Search Engine Supply Index3.68 (0.95)

This Compound (35.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.54%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other64 (98.46%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]