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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.

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  • 129558-76-5 Structure
  • Basic information

    1. Product Name: TOLFENPYRAD
    2. 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
    3. CAS NO:129558-76-5
    4. Molecular Formula: C21H22ClN3O2
    5. Molecular Weight: 383.87
    6. EINECS: N/A
    7. Product Categories: Agro-Products;Amines;Aromatics;Heterocycles;Pharmaceutical intermediates
    8. Mol File: 129558-76-5.mol
  • Chemical Properties

    1. Melting Point: 87~89℃
    2. Boiling Point: 539.982 °C at 760 mmHg
    3. Flash Point: 280.371 °C
    4. Appearance: /
    5. Density: 1.216 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.6
    8. Storage Temp.: 0-6°C
    9. Solubility: N/A
    10. PKA: 13.11±0.46(Predicted)
    11. BRN: 13666608
    12. CAS DataBase Reference: TOLFENPYRAD(CAS DataBase Reference)
    13. NIST Chemistry Reference: TOLFENPYRAD(129558-76-5)
    14. EPA Substance Registry System: TOLFENPYRAD(129558-76-5)
  • Safety Data

    1. Hazard Codes: Xn,N
    2. Statements: 20/22-50/53
    3. Safety Statements: 60-61
    4. RIDADR: UN 3077 9 / PGIII
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 129558-76-5(Hazardous Substances Data)

129558-76-5 Usage

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

Check Digit Verification of cas no

The CAS Registry Mumber 129558-76-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,9,5,5 and 8 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 129558-76:
(8*1)+(7*2)+(6*9)+(5*5)+(4*5)+(3*8)+(2*7)+(1*6)=165
165 % 10 = 5
So 129558-76-5 is a valid CAS Registry Number.
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)

129558-76-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name tolfenpyrad

1.2 Other means of identification

Product number -
Other names 4-chloro-3-ethyl-1-methyl-N-[[4-(4-methylphenoxy)phenyl]methyl]-1H-pyrazole-5-carboxamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:129558-76-5 SDS

129558-76-5Downstream Products

129558-76-5Relevant articles and documents

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

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, (2021/06/26)

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.

Method for preparing pyrazole amide compounds by using microreactor

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Paragraph 0029-0039, (2020/07/02)

The invention relates to a method for preparing pyrazole amide compounds by using a microreactor. Specifically, a solution obtained by dissolving a compound shown in a formula (A) in an organic solvent and a solution obtained by dissolving a compound shown in a formula (B) in an organic solvent are mixed through a micro-mixer and then input into a micro-channel reactor for reaction, and a reactionsolution is subjected to aftertreatment to prepare the pyrazole amide compound shown in a formula (C). According to the technical scheme, the micro-channel reactor is adopted, so that the mass transfer and heat transfer efficiency is effectively improved, the reaction rate can be effectively increased, the reaction time is greatly shortened, and the production efficiency is improved; continuous production operation can be achieved, the product quality stability is improved, the equipment integration degree is high, and the occupied space can be reduced; an acid-binding agent does not need tobe additionally added, product aftertreatment is simple, no waste salt is generated, and the product is high in yield, high in purity, safe and environmentally friendly.

Pyrazole amides and insecticide and miticide containing them as active ingredient

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, (2008/06/13)

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.

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