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Triazinone compound containing thiazole rings and preparation method and application thereof

A triazinone-containing technology containing a thiazole ring, applied in the field of agricultural and forestry insecticides, can solve the problems of no obvious lethality and resistance of moth pests, achieve good insecticidal activity, solve the problem of resistance, and high The effect of insecticidal activity

Inactive Publication Date: 2016-01-20
SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims to solve the problem that existing products have no obvious lethality and resistance to moth pests such as diamondback moth, and provides a new triazine containing a thiazole ring with the characteristics of high activity, resistance, broad spectrum, and low toxicity. Ketone organic compound and its preparation method and application

Method used

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  • Triazinone compound containing thiazole rings and preparation method and application thereof
  • Triazinone compound containing thiazole rings and preparation method and application thereof
  • Triazinone compound containing thiazole rings and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Example 1: Preparation of 2-methyl-4-acetonyl-1,3,4-oxadiazol-5-one

[0029] Add 49.6g of bromine dropwise to 85mL of acetone, after the solution becomes clear, add 90mL of triethylamine and stir for 30min, filter off triethylamine hydrogen bromide, and then add 29g (0.3mol) of 2-methyl- 1,3,4-Oxadiazol-5(4H)-one was added into the solution and refluxed for 3 hours. Desolvation gave 43g of 2-methyl-4-acetonyl-1,3,4-oxadiazol-5-one.

Embodiment 2

[0030] Example 2: Preparation of 4-amino-6-methyl-3-ketone-2,5,5-trihydro-1,2,4-triazine

[0031] Dissolve 33g (0.2mol) of 2-methyl-4-acetonyl-1,3,4-oxadiazol-5-one in 40mL of methanol, add 13g of 80% hydrazine hydrate dropwise at room temperature, reflux for 3 hours after dropping, and evaporate Remove most of the solvent, cool in an ice bath to 10°C, slowly drop into 19.5g of concentrated hydrochloric acid, react at 40°C for 4 hours, cool, and remove the solvent to obtain 17.9g of 4-amino-6-methyl-3-ketone-2, 5,5-Trihydro-1,2,4-triazine.

Embodiment 3

[0032] Embodiment 3: Preparation of 2-chloro-5-formaldehyde base thiazole

[0033] Add 33.6g (0.24mol) of hexamethylene iminium to 303g of chloroform, heat to reflux, then slowly add 32.4g (0.2mol) of 2-chloro-5-chloromethylthiazole dropwise, keep reflux after dropping 3 hours. After cooling to below 0°C with an ice bath, the obtained solid was first dissolved with 17% hydrochloric acid solution and stirred for 30 minutes, then added with 48% glacial acetic acid and heated to 60-70°C for 3 hours. Then 3×50 mL of ethyl acetate was added for extraction, and the extract was washed with 3% aqueous sodium carbonate solution, dried and precipitated to obtain 21.1 g of light yellow solid. IR(KBr) displayed at 1674cm －1 There is a strong absorption peak.

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Abstract

The invention relates to a triazinone compound containing thiazole rings and a preparation method and application thereof. The problem that an existing product does not have the obvious lethality and resistance on moth pests such as plutella xylostella is solved. The invention discloses a molecular formula, the preparation method and the application of the triazinone compound. The triazinone compound can be used for preventing and controlling insect attacks on various crops.

Description

technical field [0001] The invention belongs to the field of insecticides for agriculture and forestry, and in particular relates to a triazone compound containing a thiazole ring and a preparation method and application thereof. Background technique [0002] Triazinones are an important class of heterocyclic compounds widely used in pharmaceutical and agricultural production. It not only has remarkable curative effect in anti-cancer, anti-ulcer and anti-inflammation, but also shows good activity in agricultural fields such as weeding, desiccation, defoliation, plant growth regulation and insecticide. The series of compounds based on 1,2,4-triazin-3-one have high efficacy and unique mode of action. [0003] For example: Pymetrozine, an insecticide developed by Novartis in Switzerland, is well received by the general public due to its unique mode of action of "oral penetration steric hindrance effect", high-efficiency and long-lasting insecticidal properties, low toxicity to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/12C07D417/12A01N43/78A01N43/707A01P7/04
CPCC07D409/12A01N43/707A01N43/78C07D417/12
Inventor 岳德仁蔡琨郭伟
Owner SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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