Heterocyclic substituted 1, 3, 4-oxadiazole hydrazide compound and preparation method and application thereof

A technology of oxadiazole hydrazide and compounds, applied in the field of medicinal chemistry, can solve the problems of farmers' economic losses, quality reduction, and crop yield decline

Pending Publication Date: 2021-04-06
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In recent years, plant fungi and bacteria have seriously affected the yield and quality of crops around the world.

Method used

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  • Heterocyclic substituted 1, 3, 4-oxadiazole hydrazide compound and preparation method and application thereof
  • Heterocyclic substituted 1, 3, 4-oxadiazole hydrazide compound and preparation method and application thereof
  • Heterocyclic substituted 1, 3, 4-oxadiazole hydrazide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: Preparation of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid methyl ester

[0051] Dissolve 10.0g (56.8mmol) of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid in 100mL of methanol, then add concentrated sulfuric acid (8.0mL, 85.2mmol), at 75°C The reaction was stopped after reacting for 8 hours. After desolventization, 200 mL of ethyl acetate was added, washed with water 50 mL×3 times, dried over anhydrous sodium sulfate, and 10.5 g of a colorless oil was obtained after desolventization, with a yield of 97.2%.

[0052] For other ester intermediate compounds, corresponding raw materials or substituents are used, and are synthesized with reference to the steps of Example 1.

Embodiment 2

[0053] Example 2: Preparation of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbohydrazide

[0054] Dissolve 10.5 g (55.2 mmol) of methyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate in 50 mL of anhydrous methanol, and add hydrazine hydrate (6.0 mL, 82.8 mmol) , 0 ° C reaction 10h to stop the reaction, add petroleum ether after precipitation, and then filter the solid, dry the solid to obtain a white solid 8.7g, yield 82.9%.

[0055] Other hydrazide intermediate compounds are synthesized by referring to the steps of Example 2 using corresponding raw materials or substituents.

Embodiment 3

[0056] Example 3: Preparation of 5-(3-(difluoromethyl)-1-methyl-1H-pyrazolyl)-1,3,4-oxadiazole-2-carboxylic acid methyl ester

[0057] Dissolve 5.0g (26.3mmol) of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbohydrazide in 20mL of phosphorus oxychloride, then add methyl oxalyl chloride (3.6mL, 39.4 mmol), react at 85°C for 4h to stop the reaction, add 200mL of ethyl acetate after precipitation, wash 50mL×3 times, dry with anhydrous sodium sulfate, precipitation to obtain a brown solid, add ethanol to recrystallize to obtain a white solid 3.5g, yield 51.5 %. The melting point is 112.2-113.7°C.

[0058] For other ester intermediate compounds, corresponding raw materials or substituents are used, and are synthesized with reference to the steps of Example 3.

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Abstract

The invention relates to heterocyclic substituted 1, 3, 4-oxadiazole hydrazide compounds and a preparation method and application thereof. The compound has a structure shown as a general formula (I). The compound has a relatively good inhibition effect on pathogenic fungi and bacteria; and the compound has good inhibition effects onfusarium graminearum, potato late blight bacteria, blueberry root rot bacteria, pepper fusarium wilt, sclerotinia sclerotiorum, colletotrichum gloeosporioides, botryosphaeria dothidea, rhizoctonia solani, xanthomonas oryzae pv., ralstonia solannacearum, Xanthomonas citri, kiwi canker bacteria, Xanthomonas oryzae cucumber, Xanthomonas oryza konjak, Botryosphaeria dothidea, tomato canker pathogens, apple canker pathogens and the like.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a 1,3,4-oxadiazole hydrazide compound containing an N heterocyclic group or a 1,3,4-oxadiazole hydrazide group substitution and a preparation method thereof and application. Background technique [0002] In recent years, plant fungi and bacteria have seriously affected the yield and quality of crops around the world. Plant fungal diseases directly cause crop yield and quality reduction, and bring huge economic losses to farmers. For example, Gibberellazeae. Retch is a filamentous ascomycete, which is caused by a variety of Fusarium infection and occurs on wheat. The pathogen can cause wheat seedling rot, stalk rot, stem rot and ear rot, and it brings at least 10-20% yield reduction to wheat-growing countries every year. In addition, rice bacterial blight (Xanthomonas oryzaepv.Oryzae) is a rod-shaped Gram-negative bacterium, which can cause the leaves of rice to with...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D417/04C07D231/14A01N43/824A01N43/56A01P3/00
CPCC07D413/04C07D417/04C07D231/14A01N43/82A01N43/56
Inventor 杨松龙周卿王培义朱建军柳立伟
Owner GUIZHOU UNIV
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