Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Thiazole hydrazide compound as well as preparation method and application thereof

A technology for thiazole hydrazides and compounds, which is applied in the field of thiazole hydrazides and their preparations, and can solve the problems of crop yield decline, farmers' economic losses, and quality reduction, etc.

Active Publication Date: 2021-10-01
GUIZHOU UNIV
View PDF2 Cites 0 Cited by
  • 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. Plant fungal diseases directly cause crop yield and quality reduction, which have brought huge economic losses to farmers.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Thiazole hydrazide compound as well as preparation method and application thereof
  • Thiazole hydrazide compound as well as preparation method and application thereof
  • Thiazole hydrazide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: Preparation of ethyl 4-methyl-2-phenylthiazole-5-carboxylate

[0049] Take 5g (36.44mmol) of thiobenzamide and add it to a 150mL round-bottomed flask, then add 6.05mL (43.73mmol) of ethyl 2-chloroacetoacetate and 60mL of ethanol and raise the temperature to 100°C for about 6 hours under reflux. TLC monitors the reaction process. After the reaction is completed, the reaction is stopped; ethanol is removed by distillation under reduced pressure, and the 200mL EA dissolving system is washed 3 times with 100mL water. / EA=30 / 1) to obtain the product, 5.69 g of yellow liquid, the yield was 63.2%.

[0050] 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

[0051] Embodiment 2: Preparation of 4-methyl-2-phenylthiazole-5-carboxylic acid

[0052] Take 1g (36.44mmol) of ethyl 4-methyl-2-phenylthiazole-5-carboxylate and put it into a 100mL round bottom flask, add 2 times the amount of sodium hydroxide solution, and use 20mL of methanol as a solvent. After reacting for about 6 hours, TLC monitored the reaction process. After the reaction was completed, the reaction was stopped; methanol was distilled and desolvated under reduced pressure, concentrated hydrochloric acid was added to the system, the pH was adjusted to 2-3, suction filtered, and washed 3 times with ice water (5mL* 3), the filter cake was dried under an infrared lamp to obtain 0.61 g of a white solid with a yield of 68.8%.

[0053] Other carboxylic acid intermediate compounds are synthesized with reference to the steps of Example 2 using corresponding raw materials or substituents.

Embodiment 3

[0054] Example 3: Preparation of 4-methyl-2-phenylthiazole-N'-phenyl-5-formylhydrazide

[0055] Take 0.2g (0.91mmol) 4-methyl-2-phenylthiazole-5-carboxylic acid and add it to a 15mL pressure bottle, then add 0.35g (1.83mmol) EDCI, 0.15g (1.09mmol) HOBT, 3mL DCM Dissolve the system, add 0.14g (0.92mmol) phenylhydrazine at last, stir and react at room temperature, react for about 5h, monitor the reaction process by TLC, stop the reaction after the reaction is completed; dissolve the compound in 150mL DCM system, wash 3 times with 50mL water, add the organic phase Dry over anhydrous sodium sulfate, filter with suction, distill under reduced pressure to obtain a light yellow solid, add absolute ethanol for recrystallization, and precipitate a light yellow solid, filter with suction, wash with a small amount of absolute ethanol, and dry the compound under an infrared lamp After drying, it was weighed to obtain 0.08 g, and the yield was 28.4%. The melting point is 166.5-167.8°C.

...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Ec50aaaaaaaaaa
Login to View More

Abstract

The invention relates to a thiazole hydrazide compound as well as a preparation method and an application thereof. The compound has a structure as shown in a general formula (I). The compound has a relatively good inhibition effect on pathogenic fungi and bacteria; and has a good inhibition effect onfusarium graminearum, potato late blight bacteria, blueberry root rot bacteria, pepper fusarium oxysporum, sclerotinia sclerotiorum, colletotrichum oryzae, botryosphaeria dothidea, rhizoctonia solani, xanthomonas oryzae pv. Oryzae, ralstonia solanacearum, citrus canker germs, kiwi fruit canker germs, cucumber xanthomonas oryzae pv. Cucumerinum, Xanthomonas oryzae of konjac, Botryosphaeria dothidea, tomato canker pathogen, apple canker pathogen and the like.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a thiazole-containing hydrazide compound and a preparation method and application thereof. 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, Gibberella saubinetii 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 wither and turn white, and it brings at least 10-50% of the rice-growing countries every...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D277/56A01N43/78A01P1/00A01P3/00
CPCC07D277/56A01N43/78Y02A50/30
Inventor 王培义朱建军黄正春陈亚珍宿芬邵明政程祖红李楚楚
Owner GUIZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com