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

Derivative of 1-acyl benzimidazolone and use thereof as agricultural fungicide

A technology of acylbenzimidazolone and derivatives, applied in the field of new 1-acylbenzimidazolone derivatives and agricultural fungicides, can solve the problems of few research reports on benzimidazolone derivatives, and achieve strong inhibition Bacterial activity, inhibition of mycelium growth, and inhibition of spore germination

Inactive Publication Date: 2014-03-26
PESTICIDE INST XIBEI AGRI & FORESTRY TECHUNIV
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, with the in-depth study of pharmacological activity, the research of benzimidazolone derivatives in the field of medicine has also received extensive attention, but there are few research reports on the activity of benzimidazolone derivatives against plant pathogenic fungi

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
  • Derivative of 1-acyl benzimidazolone and use thereof as agricultural fungicide
  • Derivative of 1-acyl benzimidazolone and use thereof as agricultural fungicide
  • Derivative of 1-acyl benzimidazolone and use thereof as agricultural fungicide

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0042] The following specific preparation examples and biological examples are helpful to understand the present invention, but do not limit the content of the present invention.

[0043] The following preparation examples 1-18 further illustrate the preparation method of the compound of general formula (I) and the preparation of the present application, but are not limited thereto.

Embodiment 1

[0045] Synthesis of 3-isopropyl-2-oxo-1-pentanoyl-2,3-dihydro-1H-benzimidazole-4-carboxylic acid ethyl ester

[0046]

[0047] Weigh Ia (1.82g, 10mmol), ethanol (4.6g, 100mmol), 30mL of toluene was placed in a 100mL eggplant-shaped flask, then 3mL of concentrated sulfuric acid was added and heated to reflux for 3h, after cooling to room temperature, saturated sodium bicarbonate was added to neutralize the reaction The liquid was transferred to a separatory funnel, extracted with ethyl acetate (20 mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain Intermediate Ib (1.81 g) with a yield of 86.0%;

[0048] Weigh Ib (1.05g, 5mmol), 1.68g (30mmol) potassium hydroxide, 10mL dimethylformamide (DMF) in a 100mL eggplant flask, stir at room temperature for 30min, add 1.02g (6mmol) isopropane iodide, Continue to stir the reaction at room temperature for 15h. Add 50 mL of ethyl acetate / water (volume ratio 2 / 1)...

Embodiment 2

[0054] Synthesis of 3-allyl-1-(3-methylbenzoyl)-2-thio-2,3-dihydro-1H-benzimidazole-5-carboxylic acid ethyl ester

[0055]

[0056] Weigh IIa (1.82g, 10mmol), ethanol (4.6g, 100mmol), 30mL of toluene is placed in a 100mL eggplant-shaped bottle, then 3mL of concentrated sulfuric acid is added and heated to reflux for 3h, and intermediate IIb is obtained according to the method in Example 1 ( 1.92g), yield 91.4%;

[0057] Weigh IIb (1.05 g, 5 mmol), Boc anhydride (1.31 g, 6 mmol), 30 mL of toluene in a 100 mL eggplant-shaped flask, add triethylamine (1 mL) dropwise at room temperature, and continue stirring at room temperature for 12 h after the addition. Add 50 mL of ethyl acetate / water (volume ratio 2 / 1), stir for 10 min, transfer to a separatory funnel and let stand for layers, extract the aqueous phase with 10 mL of ethyl acetate again, combine the organic phases, and concentrate under reduced pressure to obtain an intermediate body IIc. Transfer to a 250mL three-necked...

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

No PUM Login to View More

Abstract

The invention relates to a novel derivative of 1-acyl benzimidazolone, a preparation method of the compound and use of the compound as an agricultural fungicide. The compound has the structure shown as the formula (I) in which R1, R2, R3 and X have implications referred to the specification.

Description

technical field [0001] The present invention relates to a new class of 1-acyl benzimidazolone derivatives, a preparation method of the compound, and the use of the compound as an agricultural fungicide; The field of pesticide technology. Background technique [0002] Plant disease is one of the natural disasters that seriously damage agricultural production. According to the statistics of the United Nations Food and Agriculture Organization, the global annual crop yield reduction caused by diseases is more than 10%, and more than 80% of the diseases are caused by the infection of plant pathogenic fungi. Agricultural fungicides have been used for many years in the field of crop disease control. However, with the increase in the resistance (or drug resistance) of pathogens to existing fungicides, there is an urgent need to develop fungicides with novel chemical structures. [0003] Benzimidazolone derivatives are a class of intermediates widely used in the dye industry. In ...

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): C07D235/26C07D235/28A01N43/52A01P3/00
CPCA01N43/52C07D235/26C07D235/28
Inventor 魏少鹏姬志勤吴文君
Owner PESTICIDE INST XIBEI AGRI & FORESTRY TECHUNIV
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