1, 2, 4-oxadiazole-5-formamide derivative as well as preparation method and application thereof

A technology of carboxamides and oxadiazoles, which is applied to 1,2,4-oxadiazole-5-carboxamide derivatives and the fields of preparation and application thereof, can solve the problem of unknown killing effect of plant nematodes and reduce drug consumption. The flexibility of small molecules, the lack of nematicidal activity of pine wood nematodes, etc., achieve the effects of not easy drug resistance, good environmental compatibility, and simple structure

Active Publication Date: 2022-03-22
GUIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned 1,2,4-oxadiazole derivatives have the following problems: first, in terms of antifungal activity, some compounds have good antifungal activity in vitro, but lack the evaluation of in vivo experiments, and in vivo experiments At that time, it was found that the dosage of such compounds was high, and it was difficult to apply in the field; secondly, in terms of nematodes, the nematodes targeted were relatively single, and the main target was

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  • 1, 2, 4-oxadiazole-5-formamide derivative as well as preparation method and application thereof
  • 1, 2, 4-oxadiazole-5-formamide derivative as well as preparation method and application thereof
  • 1, 2, 4-oxadiazole-5-formamide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: The preparation method of N-(2-(pyridin-2-yl) ethyl)-3-phenyl-1,2,4-oxadiazole-5-carboxamide (compound number is F1), including The following steps:

[0073] (1) Preparation of N-hydroxybenzamide:

[0074] Hydroxylamine hydrochloride (4.04g, 58.18mmol), sodium hydroxide (2.33g, 58.18mmol), and ethanol (48.48mL) were mixed in a 100mL three-necked flask, and substituted formylnitrile (5g, 48.48mmol) was added dropwise at room temperature, and heated after dropping Reflux for 6 hours; after the reaction, the reaction system was washed with water, separated, dried, suction filtered and desolvated under reduced pressure to obtain 5.54 g of N-hydroxybenzamide intermediate, with a yield of 83.92%;

[0075] (2) Preparation of ethyl 3-phenyl-1,2,4-oxadiazole-5-carboxylate:

[0076] Add N-hydroxybenzamide (5g, 36.72mmol), triethylamine (4.45g, 55.08mmol), and acetonitrile (36.72mL) into a three-necked flask, and add monoethyl oxalyl chloride (6.02g, 44.06mmol), c...

Embodiment 2

[0083] Example 2: N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl)-3-phenyl-1,2,4-oxadiazole-5-methan The preparation method of amide (compound number is F2), comprises the following steps:

[0084] Steps (1)~(4) are the same as in Example 1;

[0085] (5) The target compound N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl)-3-phenyl-1,2,4-oxadiazole-5- Preparation of formamide:

[0086] 2-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl-1-amine (0.32 g, 1.44 mmol), triethylamine (0.22 g, 2.16 mmol) and 2.88 mL were dried Add dichloromethane into a one-necked bottle, stir evenly, add 3-phenyl-1,2,4-oxadiazole-5-carbonyl chloride (0.30g, 1.44mmol) at room temperature, and keep the temperature for 9h, After the reaction system was washed with water, washed with saturated sodium bicarbonate, washed with saturated brine, separated, dried, filtered with suction and precipitated under reduced pressure, it was subjected to column chromatography using petroleum ether: ethyl ...

Embodiment 3

[0087] Embodiment 3: The preparation method of N-(2,4-difluorobenzyl)-3-phenyl-1,2,4-oxadiazole-5-carboxamide (compound number is F3), comprising the following steps:

[0088] Steps (1)~(4) are the same as in Example 1;

[0089] (5) Preparation of target compound N-(2,4-difluorobenzyl)-3-phenyl-1,2,4-oxadiazole-5-carboxamide:

[0090] Add 2,4-difluorobenzylamine (0.21g, 1.44mmol), triethylamine (0.22g, 2.16mmol) and 2.88mL of dry dichloromethane into a single-necked flask, stir well, then add 3-benzene Base-1,2,4-oxadiazole-5-carbonyl chloride (0.30g, 1.44mmol), after maintaining the temperature for 9h, the reaction system was washed with water, washed with saturated sodium bicarbonate, washed with saturated brine, separated and dried , suction filtration and desolvation under reduced pressure, using petroleum ether: ethyl acetate = 30:1 as the mobile phase through column chromatography to obtain white solid N-(2,4-difluorobenzyl)-3-phenyl- 0.24 g of 1,2,4-oxadiazole-5-carbo...

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Abstract

The invention relates to the field of chemical engineering and pesticides, in particular to a 1, 2, 4-oxadiazole-5-formamide derivative, a preparation method of the 1, 2, 4-oxadiazole-5-formamide derivative, a preparation method of the 1, 2, 4-oxadiazole-5-formamide derivative and a preparation method of the 1, 2, 4-oxadiazole-5-formamide derivative. The invention discloses application of a 1, 2, 4-oxadiazole-5-formamide derivative to preparation of drugs for preventing and treating plant diseases such as rice sheath blight disease, tomato gray mold, sclerotinia rot of colza, meloidogyne incognita, pine wood nematode, aphelenchoides besseyi and caenorhabditis elegans. The derivative is synthesized by taking substituted aromatic nitrile, hydroxylamine hydrochloride, sodium hydroxide, oxalyl chloride monoethyl ester, triethylamine, lithium hydroxide, oxalyl chloride and primary amine as raw materials through five steps of addition, cyclization, hydrolysis, chloroacylation and substitution reaction, and has the advantages of low toxicity, high yield, easiness in degradation and good environmental compatibility; the composition has the characteristics of high safety, simple preparation process, low production cost, simple structure and low possibility of generating drug resistance.

Description

technical field [0001] The present invention relates to the fields of chemical engineering and pesticides, specifically to 1,2,4-oxadiazole-5-carboxamide derivatives, and to the 1,2,4-oxadiazole-5-carboxamide derivatives The preparation method, and the 1,2,4-oxadiazole-5-carboxamide derivatives are used in the preparation and control of rice sheath blight, tomato gray mold, rape sclerotinia, root-knot nematode incognita, pine wood nematode, Application in medicines for plant diseases such as rice stem sharp nematode and Caenorhabditis elegans. Background technique [0002] In recent years, plant diseases caused by fungi and nematodes have become more and more serious, which greatly threatens the viability and health of plants. To make matters worse, the combination of fungi and nematodes often produces synergistic effects, resulting in greater crop losses than each pathogen alone or both pathogens combined. Up to now, more than 8,000 kinds of fungi are known to cause plant...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D271/10C07D413/14A01N43/82A01P3/00A01P5/00
CPCC07D413/12C07D271/10C07D413/14A01N43/82
Inventor 甘秀海刘丹王正兴曾华南袁婷梁峻铖罗领耿望
Owner GUIZHOU UNIV
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