3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole as well as synthetic process and application thereof

A trifluoromethylaniline-based, synthetic process technology, applied in the fields of application, botanical equipment and methods, insecticides, etc., can solve the problem that the skeleton structure is not a triazole ring, etc.

Active Publication Date: 2015-04-29
南雄汇星化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in pesticide research, although compounds containing triazole rings are used as pesticides, the skeleton structure is not a triazole ring.

Method used

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  • 3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole as well as synthetic process and application thereof
  • 3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole as well as synthetic process and application thereof
  • 3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole as well as synthetic process and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016]

[0017] Preparation of intermediate benzoyl isothiocyanate (3)

[0018] Add 2.10 g (21.6 mmol) of potassium thiocyanate into a 100 ml three-necked flask, and add 60 ml of acetone to dissolve. Raise the temperature to 45-50°C, slowly add dropwise a mixed solution of 2.1ml (18mmol) of benzoyl chloride and 20ml of acetone, and continue the reaction for 3-4h after the dropwise addition. Let cool to room temperature. Suction filtration, washing with acetone, the collected filtrate can be directly used in the next step. Dissolve 2.9g (18mmol) of p-trifluoromethylaniline in 20ml of acetone, and add it dropwise to benzoyl isothiocyanate (2) within 30min, and heat up to reflux for 8-9h. TLC tracking. After the reaction was completed, the solvent was evaporated to dryness, diluted with ice water, stirred evenly, and the solid was collected by suction filtration, and recrystallized with ethanol to obtain 1-benzoyl-3-(4-trifluoromethylphenyl)thiourea (3), white Needle cryst...

Embodiment 2

[0022] Preparation of intermediate benzoyl isothiocyanate (3)

[0023] Add 2.10 g (21.6 mmol) of potassium thiocyanate into a 100 ml three-necked flask, and add 60 ml of acetone to dissolve. Raise the temperature to 45-50°C, slowly add dropwise a mixed solution of 2.1ml (18mmol) of benzoyl chloride and 20ml of acetone, and continue the reaction for 3-4h after the dropwise addition. Let cool to room temperature. Suction filtration, washing with acetone, the collected filtrate can be directly used in the next step. 6.0g (36mmol) of p-trifluoromethylaniline was dissolved in 20ml of acetone, and was added dropwise to benzoyl isothiocyanate (2) within 30min, and the temperature was raised to reflux for 12h. TLC tracking. After the reaction was completed, the solvent was evaporated to dryness, diluted with ice water, stirred evenly, and the solid was collected by suction filtration, and recrystallized with ethanol to obtain 1-benzoyl-3-(4-trifluoromethylphenyl)thiourea (3), white...

Embodiment 3

[0027] The preparation of intermediate benzoyl isothiocyanate (3) is the same as in Example 1.

[0028] Add 3.0 g (9 mmol) of 1-benzoyl-3-(4-trifluoromethylphenyl)thiourea (3), 50 ml of ethanol and 5 ml of acetic anhydride into a 100 ml three-necked flask. Heat to completely dissolve the solid, and add 80% hydrazine hydrate (46 mmol) in ethanol dropwise to the above solution. Reflux for 10 hours. After the reaction was completed, a white solid was precipitated after standing for cooling. Suction filtration, the collected solid was recrystallized with absolute ethanol to obtain 0.8 g of the target compound 3-phenyl-5-(4-trifluoromethylanilino)-4H-1,2,4-triazole (4). rate 29%.

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Abstract

The invention relates to 3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole as well as a synthetic process and an application thereof. A synthetic process of 3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole comprises the following steps: 1) carrying out reaction on benzoyl chloride which is taken as a raw material and potassium thiocyanate to generate benzoyl isothiocyanate; 2) carrying out reaction on benzoyl isothiocyanate and p-trifluoromethyl phenylamine to produce an intermediate 1-benzoyl-3-(4-trifluoromethyl phenylamino) thiourea; and 3) carrying out reaction on the intermediate 1-benzoyl-3-(4-trifluoromethyl phenylamino) thiourea and hydrazine hydrate to produce a target product 3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole. The 3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole has the beneficial effects that a new compound is determined by adopting a spray method when concentration of a target compound is 200ppm, the efficiency of protecting malt in 24 hours is 60%, the efficiency of protecting malt in 48 hours is 70%, and the 3-phenyl-5-(4-trifluoromethyl phenylamino)-4H-1,2,4-triazole has a potential of being further developed into an insecticide.

Description

technical field [0001] The invention relates to triazole compounds, specifically 3-phenyl-5-(4-trifluoromethylanilino)-4H-1,2,4-triazole and its synthesis process and application. technical background [0002] Triazole compounds have a wide range of physiological activities. In the 1970s, the high-efficiency bactericidal activity of triazole compounds attracted great attention from the international pesticide industry. It was found that the substituent group on the N-methyl carbon can be widely used by other groups. The biological activity remained unchanged or improved. Through the transformation of substituent groups (for example, phenyl can be substituted by five-membered or six-membered heterocyclic rings, various types of saturated or unsaturated alkyl groups, esters, ketones and other functional groups or bridge benzyl groups), synthesize and screen out a A batch of triazole compounds with fungicidal activity. These include highly active triazolyl-O, N-acetal compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/14A01N43/653A01P7/04
CPCA01N43/653C07D249/14
Inventor 巨修练乔恒余勇
Owner 南雄汇星化工科技有限公司
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