ChemicalBook--->CAS DataBase List--->951659-40-8

951659-40-8

951659-40-8 Structure

951659-40-8 Structure
IdentificationBack Directory
[Name]

Flupyradifurone
[CAS]

951659-40-8
[Synonyms]

Flupyradifurone
Flupyradifurone Solution
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
2(5H)-Furanone, 4-[[(6-chloro-3-pyridinyl)methyl](2,2-difluoroethyl)amino]-
4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl) amino}-2,5-dihydrofuran-2-one
[Molecular Formula]

C12H11ClF2N2O2
[MDL Number]

MFCD22373627
[MOL File]

951659-40-8.mol
[Molecular Weight]

288.68
Chemical PropertiesBack Directory
[Melting point ]

69 - 71°C
[Boiling point ]

457.7±45.0 °C(Predicted)
[density ]

1.41±0.1 g/cm3(Predicted)
[storage temp. ]

Refrigerator
[solubility ]

DMSO (Slightly, Sonicated), Methanol (Slightly)
[form ]

neat
[pka]

0.22±0.10(Predicted)
[color ]

White to Pale Brown
[BRN ]

19518067
[Henry's Law Constant]

6.5×106 mol/(m3Pa) at 25℃, Ebert et al. (2023)
[InChI]

1S/C12H11ClF2N2O2/c13-10-2-1-8(4-16-10)5-17(6-11(14)15)9-3-12(18)19-7-9/h1-4,11H,5-7H2
[InChIKey]

QOIYTRGFOFZNKF-UHFFFAOYSA-N
[SMILES]

FC(F)CN(Cc1ccc(Cl)nc1)C2=CC(=O)OC2
[LogP]

1.110 (est)
[EPA Substance Registry System]

2(5H)-Furanone, 4-[[(6-chloro-3-pyridinyl)methyl](2,2-difluoroethyl)amino]- (951659-40-8)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[WGK Germany ]

2
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
STOT RE 2
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Tetronic acid-->p-Toluenesulfonic acid-->2-Chloro-5-(chloromethyl)pyridine
Hazard InformationBack Directory
[Description]

Flupyradifurone(FPF) is a novel butenolide insecticide developed for foliar, soil and seed treatment applications (Nauen et al., 2015). FPF was commercially introduced to the market in 2014 as an integrated pest management (IPM)-friendly tool (Bordini et al., 2021), and is registered for use in a wide variety of fruit and vegetable crops and defined broad acre crops. It targets some of the world′s most destructive sucking pests including aphids, psyllids, scales, leafhoppers, mealy bugs, and is particularly important for the control of whiteflies such as Bemisia tabaci, a vector of serious phytopathogenic viruses such as tomato yellow leaf curl virus and cucurbit yellow stunting disorder virus (Castle et al., 2017; Roditakis et al., 2017).
[Uses]

Flupyradifurone, can be used as an insecticide.
[Definition]

ChEBI: Flupyradifurone is 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. It has a role as a nicotinic acetylcholine receptor agonist and an insecticide. It is a butenolide, a monochloropyridine, an organofluorine insecticide, an enamine and a tertiary amino compound.
[Preparation]

Two different pathways for the synthesis of flupyradifurone
Starting from tetronic acid, one approach consists in two consecutive reactions. Where the tetronic acid reacts firstly with a difluoroethane-1-amine and secondly with 2-Chloro-5- (chloromethyl)pyridine.
synthesis of flupyradifurone
And the other approach, where the tetronic acid reacts with difluoroethane-1-amine derivative in the presence of 4-toluenesulfonic acid in a “one pot” approach to yield flupyradifurone.
[Mechanism of action]

Systemic. It is an adult knockdown product that also offers some control of nymph and egg stages. Nicotinic acetylcholine receptor (nAChR) channel blocker.
[in vivo]

The half-life of Flupyradifurone in peppers is 2.6-3.8 days. The national estimated daily intake of Flupyradifurone is 0.00094 mg/kg[3].

[storage]

4°C, protect from light
[Pesticide Type]

Insecticide
Spectrum DetailBack Directory
[Spectrum Detail]

Flupyradifurone(951659-40-8)1HNMR
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