129558-76-5

Basic information

• Product Name: TOLFENPYRAD
• Synonyms: TOLFENPYRAD;omi-88;tolfenpyrad (bsi, pa iso);TOLFENPYRAD STANDARD;HATI-HATI;4-chloro-3-ethyl-1-Methyl-N-(4-(p-tolyloxy)benzyl)-1H-pyrazole-5-carboxaMide;1H-Pyrazole-5-carboxaMide, 4-chloro-3-ethyl-1-Methyl-N-[[4-(4-Methylphenoxy)phenyl]Methyl]-;4-Chloro-3-ethyl-1-methyl-N-[4-(p-tolyloxy)benzyl]pyrazole-5-carboxamide
• CAS NO: 129558-76-5
• Molecular Formula: C₂₁H₂₂ClN₃O₂
• Molecular Weight: 383.87
• Product Categories: Agro-Products;Amines;Aromatics;Heterocycles;Pharmaceutical intermediates
• Mol File: 129558-76-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 87～89℃
• Boiling Point: 539.982 °C at 760 mmHg
• Flash Point: 280.371 °C
• Appearance: /
• Density: 1.216 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: 0-6°C
• PKA: 13.11±0.46(Predicted)
• BRN: 13666608
• CAS DataBase Reference: TOLFENPYRAD(CAS DataBase Reference)
• NIST Chemistry Reference: TOLFENPYRAD(129558-76-5)
• EPA Substance Registry System: TOLFENPYRAD(129558-76-5)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20/22-50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 129558-76-5(Hazardous Substances Data)

Usage

Description

Tolfenpyrad is a pyrazole insecticide developed by Mitsubishi Chemical. It was first approved in 2002 in Japan under the trade name of Hachi-hachi. It has broad insecticidal activity against a variety of pests such as Hemiptera, Coleoptera, Diptera, Lepidoptera, Thysanoptera and Acarina. It is especially effective against pests that are resistant to existing insecticides such as organophosphates and carbametes, because it supposedly possesses a new mode of action: inhibition of Complex I in the respiratory electron-transfer chain of mitochondria. It is applied for vegetables particularly cruciferous leafy varieties, cucurbits, cole crops, tea, fruits & nuts, selected row crops, and indoor ornamentals except cut flowers.

References

[1] http://sitem.herts.ac.uk/aeru/iupac/Reports/1687.htm ? [2] Koji Yamaguchi,? Wakako Hikiji, Masahiko Takino, Kanju Saka, Makiko Hayashida, Tatsushige Fukunaga, Youkichi Ohno (2012) Analysis of Tolfenpyrad and its Metabolites in Plasma in a Tolfenpyrad Poisoning Case, 36, 529-537

Uses

Tolfenpyrad

Definition

ChEBI: An aromatic amide obtained by formal condensation of the carboxy group of 4-chloro-3-ethyl-1-methylpyrazole-5-carboxylic acid with the amino group of 1-[4-(4-methylphenoxy)phenyl]methylamine.

InChI:InChI=1/C21H22ClN3O2/c1-4-18-19(22)20(25(3)24-18)21(26)23-13-15-7-11-17(12-8-15)27-16-9-5-14(2)6-10-16/h5-12H,4,13H2,1-3H3,(H,23,26)

Upstream product

• 129560-03-8 (4‐(p‐tolyloxy)phenyl)methanamine 
• 37563-42-1 4-(4'-methylphenoxy)benzonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 106-44-5 p-cresol 
• 129560-00-5 1-methyl-3-ethyl-4-chloro-1H-pyrazol-5-ylformylic acid chloride 
• 262862-66-8 4-(4-methylphenoxy)benzylamine hydrochloride 

Relevant articles and documents

Preparation method of substituted phenoxy benzylamine compound and preparation method of pyrazole carboxamide compound

The invention discloses a preparation method of a substituted phenoxy benzylamine compound. P-halobenzonitrile is taken as an initial raw material, R'OH is taken as a solvent in the presence of R'OM, the substituted phenoxy benzylamine compound is obtained through hydrogen reduction, and the preparation method has the advantages of high yield and high purity. The invention also discloses a preparation method of pyrazole carboxamide. The preparation method of pyrazole carboxamide comprises the following steps: salifying the substituted phenoxy benzylamine compound, and reacting with a substituted pyrazole acyl chloride compound to prepare the pyrazole carboxamide compound at an expected high yield. The preparation methods provided by the invention have the advantages of high product purity, high yield, low solvent loss and low production cost.

Pyrazole amides and insecticide and miticide containing them as active ingredient

Novel pyrazole amide and an insecticidal and miticidal composition containing the pyrazole amide as an active ingredient are described. The pyrazole amide according to the present invention shows excellent insecticidal and miticidal activities.