Pentadienone compound containing quinazolinone aryloxy group, preparation method and application

A technology containing quinazolinone aryloxy group and pentadienone is applied in the field of pentadienone derivatives and their preparation, and can solve the problem that no pentadienone derivatives have ever been synthesized and have less resistance to plant viruses. And other issues

Inactive Publication Date: 2016-01-13
GUIZHOU UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Known from background technology, quinazolinone compound and 1,4-pentadien-3-ketone compound all have the biological activity of respect such as anti-plant virus preferably, but about containing quinazolinone aryloxyl group Pentadienone derivatives have not yet been synthesized, and there are few domestic and foreign research reports on the anti-plant virus of this type of compound

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
  • Pentadienone compound containing quinazolinone aryloxy group, preparation method and application
  • Pentadienone compound containing quinazolinone aryloxy group, preparation method and application
  • Pentadienone compound containing quinazolinone aryloxy group, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1, (1E,4E)-3-((2-(3-oxo-5-phenyl-1,4-pentadien-1-yl)phenoxy)methyl)quinazoline- Synthesis of 4-(3H)-ketone (A1)

[0066] (1) Synthesis of quinazolin-4-(3H)-one

[0067]Add 27.5g (0.2mol) of anthranilic acid and 36.1g (0.8mol) of formamide into a 250mL three-necked flask equipped with a thermometer and a condenser to keep the temperature at 135-150°C. During this process, the system turns from light gray to turbid The liquid turns into a yellow-brown clear liquid, TLC followed the reaction, and the reaction was complete in about 5 hours. Slowly add 100mL of water to the system after cooling down to 100°C naturally to decompose excess formamide, and a light gray solid precipitates out at the same time. After natural cooling Transfer to a large beaker, then add a large amount of water and there is still off-white solid precipitation, suction filtration, drying to obtain 28.88g of the product, recrystallization with absolute ethanol to obtain 27.5g of brown-white n...

Embodiment 2

[0078] Embodiment 2, the synthesis of compound (A2)

[0079] Steps (1)-(4) are the same as the steps (1)-(4) of Embodiment 1;

[0080] The difference between step (5) and step (5) of Example 1 is that: add 0.78g (5.56mmol) p-chlorobenzaldehyde instead of 0.58g (5.5mmol) benzaldehyde, react for 10h, and obtain 1.23g yellow solid, melting point ° C, yield Rate 86.5%;

[0081] The difference between step (6) and Example 1 step (6) is: add 0.37g (1.31mmol) 1-(4-chlorophenyl)-5-(2-hydroxyphenyl)-1,4-pentadiene -3-one, replace 0.33g (1.31mmol) 1-(2-hydroxyphenyl)-1,4-pentadien-3-one, react for 8h, recrystallize to get 0.23g white solid, melting point 195-197℃ , yield 39.6%.

Embodiment 3

[0082] Embodiment 3, the synthesis of compound (A3)

[0083] Step (1)-(4) is the same as embodiment 1(1)-(4);

[0084] Step (5) is the same as embodiment 1 (5) method and condition. The difference is that 0.68g (5.49mmol) 1-(2-fluorophenyl)-5-(2-hydroxyphenyl)-1,4-pentadien-3-one was added and reacted for 10h to obtain 1.10g yellow solid, Yield 82.1%.

[0085] Step (6) is the same as embodiment 1 (6) method and condition. The difference is that 0.35g (1.31mmol) 1-(2-fluorophenyl)-5-(2-hydroxyphenyl)-1,4-pentadien-3-one was added, reacted for 5h, and recrystallized to obtain 0.25g yellow Solid, melting point 142-144°C, yield 44.7%.

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
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to view more

Abstract

The invention discloses a compound of resisting plant viruses: a pentadienone compound containing quinazolinone aryloxy and a preparation method and biological activity. The invention introduces a series of novel pentadienone derivatives containing quinazolinone aryloxy which are synthesized by six steps by taking substituted o-aminobenzoic acid, formamide, 35% formalin, 1, 4-dioxane, thionyl chloride, hydroxyl benzaldehyde, acetone, sodium hydroxide, hydrochloric acid, potassium carbonate, potassium iodide, substituted aromatic aldehyde, substituted heterocyclic aldehyde and the like as raw materials. The compound disclosed by the invention further has higher treating, protecting and passivating and inhibiting effects to cucumber mosaic virus (CMV), tobacco mosaic virus (TMV), southern rice black streaked dwarf virus (SRBSDV) and rice stripe virus (RSV), shows higher anti-plant virus activity, and can be used for preparing anti-plant virus pesticides.

Description

technical field [0001] The invention relates to pentadienone derivatives containing quinazolinone aryloxy group with anti-plant virus effect and a preparation method thereof. Background technique [0002] Quinazolinone compounds have good biological activity and environmental friendliness, and have become one of the hotspots of pesticide and pharmaceutical research at home and abroad in recent years. In terms of pesticides, quinazolinone compounds have biological activities such as antibacterial, antiviral, and acaricidal. Wherein fenazaquin (EL-436) is a kind of efficient novel acaricide with simple structure that Wright of U.S. Dow-Elanco Company (Dow AgroSciences) released in the late 1980s; commercialized fluquinazole ( Fluquinconazole) is a triazole fungicide with a quinazolinone structure developed by Schering, which has a good inhibitory effect on the biosynthesis of ergosterol. At the same time, it has protective, therapeutic and systemic activities, and is very eff...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/88C07D409/12C07D405/12C07D417/12C07D401/12A01P1/00
CPCA01N43/54A01N43/78C07D239/90C07D401/12C07D405/12C07D409/12C07D417/12
Inventor 胡德禹马娟宋宝安薛伟万治华金林红贺鸣陈卓李向阳
Owner GUIZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap