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, developed by Mitsubishi Chemical, is a pyrazole insecticide first approved in 2002 in Japan under the trade name Hachi-hachi. It is 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. Tolfenpyrad exhibits broad insecticidal activity against various pests, including Hemiptera, Coleoptera, Diptera, Lepidoptera, Thysanoptera, and Acarina. It is particularly effective against pests resistant to conventional insecticides like organophosphates and carbamates due to its unique mode of action, which involves the inhibition of Complex I in the respiratory electron-transfer chain of mitochondria.

Uses

Used in Agriculture:
Tolfenpyrad is used as an insecticide for various crops to control a wide range of pests. Its application reason is its broad-spectrum activity and effectiveness against insecticide-resistant pests.
Used in Vegetable Production:
Tolfenpyrad is used as an insecticide for vegetables, particularly cruciferous leafy varieties, to protect them from pests and ensure a healthy yield.
Used in Cucurbit Production:
Tolfenpyrad is used as an insecticide for cucurbits, such as cucumbers, melons, and gourds, to control pests and maintain crop quality.
Used in Cole Crop Production:
Tolfenpyrad is used as an insecticide for cole crops, including cabbage, broccoli, and cauliflower, to prevent pest damage and improve yield.
Used in Tea Production:
Tolfenpyrad is used as an insecticide in tea cultivation to protect the tea plants from pests and ensure the quality of the final product.
Used in Fruit and Nut Production:
Tolfenpyrad is used as an insecticide for fruits and nuts to control pests and maintain the quality and yield of these crops.
Used in Selected Row Crops:
Tolfenpyrad is used as an insecticide for selected row crops to protect them from pests and ensure a healthy harvest.
Used in Indoor Ornamental Plants (except cut flowers):
Tolfenpyrad is used as an insecticide for indoor ornamental plants to control pests and maintain the plants' health and appearance.

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

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

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

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.