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1,2,4-triazole compounds and their salts and applications

A compound and triazole technology, applied in the field of 1,2,4-triazole compounds and their salts and applications, can solve problems such as limited applications

Active Publication Date: 2020-10-27
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the serious resistance problem caused by its excessive and frequent use and the cross-resistance between insecticides caused by structural similarity, the application of this type of compound is limited to a certain extent.

Method used

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  • 1,2,4-triazole compounds and their salts and applications
  • 1,2,4-triazole compounds and their salts and applications
  • 1,2,4-triazole compounds and their salts and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazole (1)

[0028] Add 0.5g of key intermediate a and 20mL of hydrazine hydrate to a 100mL three-necked flask in turn, and heat to reflux for 2 hours. After the reaction, add an appropriate amount of water to the reaction solution, and a white solid precipitates out. Filter and recrystallize with ethanol to obtain a powder Solid, melting point 309-310°C.

Embodiment 2

[0030] Preparation of 3,5-bis(2-hydroxyphenyl)-1-phenyl-1,2,4-triazole (2)

[0031] In a 150mL three-necked flask, add 20mL of absolute ethanol, 1mL of phenylhydrazine (d), 0.5g of key intermediate a, and 0.5mL of acetic acid as a catalyst. Heated to reflux for 2 hours. After the reaction, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain a white solid with a melting point of 150-151°C.

Embodiment 3

[0033] Preparation of 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid (3)

[0034] Dissolve 1.75g ​​of 4-hydrazinobenzoic acid (e) and 1.16g of NEt3 completely in 30mL of hot ethanol solution, add 2.50g of key intermediate a, and heat to reflux for 2-3h. After the reaction, concentrate under reduced pressure to half the volume, add an appropriate amount of water, adjust the pH to 5 with hydrochloric acid, a white floc is formed, and filter and purify to obtain a light yellow solid with a melting point of 261-262°C.

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Abstract

The invention discloses a 1,2,4-triazole compound, salt thereof and applications of the compound and salt. The compound has a structural formula shown in the description, wherein R represents hydrogen, phenyl or substituted phenyl, and a substituted group of substituted phenyl is selected from carboxyl, an ester group, C1-4 alkyl, C1-4 alkoxy groups, C1-4 halogenated alkyl, C1-4 halogenated alkoxygroups, C2-4 alkynyl, halogen, cyano groups, acyl, nitryl or hydroxyl. The compound has high insecticidal activity for aphids, part of compound has the insecticidal activity for aphids equivalent tothat of a commercial insecticide dinotefuran, and the compound can be used for controlling lepidoptera pests, coleoptera pests, heteropteran pests, diptera pests, orthoptera pests and homoptera pests.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to 1,2,4-triazole compounds and their salts and applications. Background technique [0002] Neonicotinoid insecticides are insecticides that have developed very rapidly in recent years. There have been three generations of commercial products, among which are representative Fipronil (common name imidacloprid, trade name Hailier Jiaqiao), Thiamethoxam (generic Name thiamethoxam, trade name Ruisheng), Dinotefuran (common name dinotefuran, trade name Nurui) their structural formulas are as follows: [0003] [0004] The first-generation neonicotinoid insecticide imidacloprid was discovered by Bayer in Switzerland in 1985 and commercialized in 1991. Imidacloprid has broad-spectrum, high-efficiency, good systemic, stomach-killing, antifeedant effects, low toxicity to mammals, and environmental safety. It can effectively control a variety of piercing-sucking and chewing...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08A01N43/653A01P7/04
CPCA01N43/653C07D249/08
Inventor 邹志红范长春秦敏王岩焦淑琳
Owner SOUTHEAST UNIV
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