119168-77-3

Basic information

• Product Name: 4-Chloro-N-(4-tert-butylbenzyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide
• Synonyms: TEBUFENPYRAD;PYRANICA;OSCAR;1h-pyrazole-5-carboxamide,4-chloro-n-((4-(1,1-dimethylethyl)phenyl)methyl)-3-e;4-chloro-n-((4-(1,1-dimethylethyl)phenyl)methyl)-3-ethyl-1-methyl-1h-pyrazol;4-chloro-n-((4-(1,1-dimethylethyl)phenyl)methyl)-3-ethyl-1-methyl-1h-pyrazole-5-carboxamid;ac801757;e-5-carboxamide
• CAS NO: 119168-77-3
• Molecular Formula: C₁₈H₂₄ClN₃O
• Molecular Weight: 333.86
• EINECS: 242-070-7
• Product Categories: Herbicide;INSECTICIDE;Agro-Products;Aromatics;Heterocycles;NULL
• Mol File: 119168-77-3.mol

Chemical Properties

• Melting Point: 61-62°
• Boiling Point: 468.4 °C at 760 mmHg
• Flash Point: 237.1 °C
• Appearance: /
• Density: 1.1639 (rough estimate)
• Vapor Pressure: 5.99E-09mmHg at 25°C
• Refractive Index: 1.5790 (estimate)
• Storage Temp.: 0-6°C
• PKA: 13.19±0.46(Predicted)
• BRN: 8636471
• CAS DataBase Reference: 4-Chloro-N-(4-tert-butylbenzyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-N-(4-tert-butylbenzyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide(119168-77-3)
• EPA Substance Registry System: 4-Chloro-N-(4-tert-butylbenzyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide(119168-77-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• RIDADR: 2588
• WGK Germany: 3
• RTECS: UQ6276400
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 119168-77-3(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
4-Chloro-N-(4-tert-butylbenzyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide is used as an acaricide for controlling and eliminating mites and other small arthropods that are harmful to crops. Its effectiveness in targeting these pests helps to protect plants and increase agricultural yields.
Used in Pest Control:
In the pest control industry, 4-Chloro-N-(4-tert-butylbenzyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide is used as an insecticide to manage and reduce insect populations that can cause damage to various environments, including residential, commercial, and industrial settings.
Used in Commercial Greenhouses:
4-Chloro-N-(4-tert-butylbenzyl)-3-ethyl-1-methyl-1H-pyrazole-5-carboxamide is also utilized in commercial greenhouses as a means to protect valuable plant species from infestations of mites and insects. Its application in this context helps maintain the health and quality of the plants being grown, ensuring a consistent supply of high-quality produce for consumers.
Chemical Properties:
The compound is described as a tan solid, which indicates its physical appearance and state at room temperature. This characteristic is important for its formulation and application methods in various industries.

Metabolic pathway

By incubation of tebufenpyrad with rat liver homogenate, tebufenpyrad undergoes biotransformation to yield the major metabolites N-(4- tert-butylbenzyl)-4-chloro-3-(1-hydroxyethyl)-1- methylpyrazole-5-carboxamide via hydroxylation of the w-1-carbon of the ethyl group and N-[4-(1-carboxy-1- methylethyl)benzyl]-4-chloro-3-ethyl-1-methylpyrazole- 5-carboxamide via oxidation of the methyl group in the tert-butyl moiety to the carboxylic acid derivatives.When the rat is orally dosed tebufenpyrad, the major metabolism pathway is via both hydroxylation and oxidation reactions to yield N-[4-(1-carboxy-1- methylethyl)benzyl]-4-chloro-3-(1-hydroxyethyl)-1- methylpyrazole-5-carboxamide which is mainly excreted in the urine.

InChI:InChI=1/C18H24ClN3O/c1-6-14-15(19)16(22(5)21-14)17(23)20-11-12-7-9-13(10-8-12)18(2,3)4/h7-10H,6,11H2,1-5H3,(H,20,23)

Synthetic route

1-methyl-3-ethyl-4-chloro-1H-pyrazol-5-ylformylic acid chloride + 4-(1,1-dimethylethyl)-benzenemethanamine (39895-55-1) → tebufenpyrad (119168-77-3)

Conditions	Yield
In toluene at 50℃; for 0.138889h; Time; Temperature;	95.8%

4-chloro-5-ethyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester + 4-(1,1-dimethylethyl)-benzenemethanamine (39895-55-1) → tebufenpyrad (119168-77-3)

Conditions	Yield
Stage #1: 4-(1,1-dimethylethyl)-benzenemethanamine With sodium hydride In tetrahydrofuran Inert atmosphere; Stage #2: 4-chloro-5-ethyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester In tetrahydrofuran at 25℃; for 3h; Inert atmosphere;	75%

ethyl 4-chloro-3-ethyl-1-methylpyrazole-5-carboxamide + 4-(1,1-dimethylethyl)-benzenemethanamine (39895-55-1) → tebufenpyrad (119168-77-3)

Upstream product

• 39895-55-1 4-(1,1-dimethylethyl)-benzenemethanamine 
• 129560-00-5 1-methyl-3-ethyl-4-chloro-1H-pyrazol-5-ylformylic acid chloride 

Relevant articles and documents

Method for preparing pyrazole amide compounds by using microreactor

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.

ACTIVE COMPOUND COMBINATIONS HAVING INSECTICIDAL AND ACARICIDAL PROPERTIES

The novel active compound combinations comprising a compound of the formula (I-1) or (I-2) and the active compounds (1) to (26) listed in the description have very good insecticidal and acaricidal properties.

Synthesis of fully substituted pyrazoles via regio- and chemoselective metalations

The full functionalization of the pyrazole ring was achieved by successive regioselective metalations using TMPMgCI-LiCI and TMP2Mg.2LiCI. Trapping with various electrophiles led to trisubstituted pyrazoles. An application to the synthesis of the acaricide Tebufenpyrad is reported.

Stabilized AGchemical concentrate and use thereof

The present invention relates to the stabilization of an agricultural chemical concentrate in aqueous solution and the stabilized concentrate which comprises: (a) between about 0.1 and about 20 wt. % of a stabilizer composition comprising: (1) a C1 to C12 alkyl vinyl ether/organic acid ester copolymer, and (2) a polymer solubilizing amount of an aromatic petroleum distillate or an oxygen-containing solvent of an N-alkyl pyrrolidone, a C3 to C8 alkanol, a dibasic acid lower alkyl ester, an ether having a boiling point above 150° C. or mixtures thereof and (b) between about 80 and about 99.9 wt. % concentrate containing a water-insoluble active agricultural chemical, a solvent for said agricultural chemical and a surfactant for said concentrate. The invention also relates to the use of said stabilized concentrate.

Stabilized agchemical concentrate and use thereof

The present invention relates to the stabilization of an agricultural chemical concentrate in aqueous solution and the stabilized concentrate which comprises: (a) between about 0.1 and about 20 wt. % of a stabilizer composition comprising: (1) between about 10 and about 90 wt. % of a water-insoluble, non-crosslinked, film forming polymer, and (2) a polymer solubilizing amount of an aromatic petroleum distillate or an oxygen-containing solvent of an N-alkyl pyrrolidone, a C3 to C8 alkanol, a dibasic acid lower alkyl ester, an ether having a boiling point above 150° C. or mixtures thereof and (b) between about 80 and about 99.9 wt. % concentrate containing a water-insoluble active agricultural chemical, a solvent for said agricultural chemical and a surfactant for said concentrate. The invention also relates to the use of said stabilized concentrate.

Insecticidal and synergistic miticidal compositions

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