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Preparation method and application of 6-fluoroquinazoline derivatives containing disulfide structures

A kind of fluoroquinazoline, disulfide technology, applied in the field of pesticides, can solve the problem of low antibacterial activity and the like

Pending Publication Date: 2021-12-07
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The structure-activity relationship shows that the substituted amino groups at positions 2 and 4 are necessary for anti-Staphylococcus aureus. In addition, when the 6 / 7 / 8 positions of the benzene ring are substituted by chlorine, its antibacterial activity is lower than that of unsubstituted compounds

Method used

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  • Preparation method and application of 6-fluoroquinazoline derivatives containing disulfide structures
  • Preparation method and application of 6-fluoroquinazoline derivatives containing disulfide structures
  • Preparation method and application of 6-fluoroquinazoline derivatives containing disulfide structures

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Synthesis of 4- (ethyl di-sulfide) -6-fluorozoline

[0042] (1) Preparation of 6-fluoroquinate-4-sulfhydryl group

[0043] 30 g2-amino 5-fluorobenzoic acid, 60 ml of formamide was added to 150 ml of round bottom flask, and the stirring was raised to 120 ° C, and the reflux reaction was about 5 h, TLC tracking, after the reaction, fell to room temperature, poured into the appropriate amount of ice water The pH was adjusted to a weak alkaline, filtered to give 5-fluofluorozolinone crude. 3.8 g (23.15 mmol) was added to 100 ml round bottom flask, and chlorinated sulfoxide (16.79 mL, 231.51 mmol) was added to stir up to 84 ° C for reflux reaction, and the catalytic amount of DMF was added dropwise during the temperature rise. After 4 hours, the heating was stopped, and most of the solvent was removed, quenched in batches, precipitated the white solid, filtered to give 4-chloro-6-fluoroquinazoline. Take tetrahydrofuran as a solvent, taking 4 g (21.91 mmol) 4-chloro-6-...

Embodiment 2

[0048] Example 2: Synthesis of 4- (propyl di-sulfide ether) -6-fluorozoline

[0049] Preparation of 6-fluoroquinazoline-4-mercapto group Example 1 Example 1; Preparation of propyl apropanine and preparation of 4- (propactiacyl ether) -6-fluoroquanoline Refer to Example 1, of which sulfonyl chloride , The molar ratio of propyl alcohol and 6-fluoroquinazoline-4-mercapto group is 4: 2: 1.

Embodiment 3

[0050] Example 3: Synthesis of 4- (butyl dithiosis ether) -6-fluorozoline

[0051] Preparation of 6-fluoroquinazoline-4-Sulfhydryl group Example 1 Example 1 Example 1 Example 1 Example 1 Preparation of Butyl Sulfonia and Preparation of 4- (Butyl Disborne Eester) -6-Fluoroquanoline Refer to Example 1, of which sulfonyl chloride However, the molar ratio of butylthiol and 6-fluoroquinazoline-4-mercapto group is 4: 2: 1.

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Abstract

The invention relates to a preparation method and application of 6-fluoroquinazoline derivatives containing disulfide structures. The compound has a structure as shown in a general formula (I) which is described in the specification. According to the invention, 6-fluoroquinazoline is taken as a parent structure, disulfanyl (heterocyclic) structures are introduced into a system, so a series of 6-fluoroquinazoline derivatives containing the disulfide structures are synthesized; and the series of compounds have a very good inhibition effect on plant pathogenic bacteria such as rice bacterial leaf blight, ralstonia solanacearum, Pseudomonas syringae pv. actinidiae, Xanthomonas axonopodis pv. citri and the like.

Description

Technical field [0001] The present invention relates to the technical field of pesticide, it is a kind of preparation and use of 6-fluoro quinazoline derivatives containing a disulfide structure. Background technique [0002] Plant pathogens seriously affecting the yield and quality of agricultural products around the world, more and more types of bacteria are found by people year after year, but the main cause of decline in crop yield and quality priority pathogens we need to consider, for example, R. solanacearum eggplant (Ralstonia solanacearum, Rs), its host involves more than 200 kinds of plants, including potatoes, tobacco, tomato, eggplant, peanuts and other important crops. Xanthomonas pathogen is a large class of metal, comprising 27 plants pathogens, the host about 400 species of plants (monocots relates and dicots), colony morphology is yellow, the yellow cells always protect themselves by secreting from light. Xanthomonas after leaving the host, can survive for some t...

Claims

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Application Information

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IPC IPC(8): C07D239/93A01N43/54A01P3/00A01P1/00
CPCC07D239/93A01N43/54
Inventor 欧阳贵平朱梅王贞超李焱樊思莉陶世林
Owner GUIZHOU UNIV
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