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A kind of thiazole bisamide compound and its preparation method and application

A technology of thiazole bisamide and compound is applied in the field of novel thiazole bisamide compound and its preparation, and achieves the effect of good bactericidal activity

Inactive Publication Date: 2018-03-20
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such fungicides have serious resistance problems due to long-term use

Method used

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  • A kind of thiazole bisamide compound and its preparation method and application
  • A kind of thiazole bisamide compound and its preparation method and application
  • A kind of thiazole bisamide compound and its preparation method and application

Examples

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preparation example Construction

[0033] In a second aspect, the present invention provides a method for preparing thiazole bisamides, the method comprising the following steps:

[0034] (1) The intermediate shown in formula (II), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole and N,N- Dimethylformamide for the first contact;

[0035] (2) put R 3 -NH 2 Shown intermediate carries out second contact with the product after step (1), wherein, R 3 is a substituted or unsubstituted diphenyl ether group, 2-biphenyl, 3-biphenyl, 4-biphenyl or phenyl; R 3 Substituents in include fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, methoxy, ethoxy, n-propoxy, isopropoxy and cyano At least one of the radicals and methyl, ethyl, n-propyl, isopropyl, cyclopropyl, methoxy, ethoxy, n-propoxy and isopropoxy substituted by halogen elements at least one; and

[0036] (3) purifying the product after step (2);

[0037] where, in formula (II), R 1 is ...

preparation example 1-5

[0082] This preparation example is used to illustrate the preparation of the intermediate represented by formula (III) according to the method I of the present invention.

[0083] Under nitrogen protection, the R 1 The reactant (10mmol) shown in -CHO, the reactant (10mmol) shown in the formula (IV), the reactant (10mmol) shown in the formula (V) and the reactant (10mmol) shown in the formula (VI) dissolve In 10mL of anhydrous methanol, react at a temperature of 25°C for 24 hours; after the reaction is complete, remove the solvent from the reaction product under reduced pressure and directly use it in the next reaction;

[0084] The crude product obtained in the previous step was dissolved in 10 mL of trifluoroacetic acid, and reacted at 50°C for 12 hours; after the reaction was complete, the solvent was removed under reduced pressure, and purified by column chromatography to obtain product intermediates marked as III-1~III-5 .

[0085] Among them, R 1 As shown in Table 1;

...

preparation example 6-20

[0092] This preparation example is used to illustrate the preparation of the intermediate represented by formula (III) according to the method II of the present invention.

[0093] Under nitrogen protection, the R 1 The reactant (10mmol) represented by -CHO, R 2 -NH 2 The reactant (10mmol) shown, the reactant (10mmol) shown in formula (V) and the reactant (10mmol) shown in formula (VI) were dissolved in 10mL of anhydrous methanol and reacted at a temperature of 25°C for 24h ; After the reaction is complete, the reaction product is desolvated under reduced pressure, and purified by column chromatography to obtain product intermediates marked as III-6~III-20.

[0094] Among them, R 1 and R 2 As shown in table 2;

[0095] Specifically, the reaction process is shown in reaction formula (4); and

[0096] Results The prepared products and their yields are shown in Table 2.

[0097] Table 2

[0098] serial number

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Abstract

The invention relates to the fields of pesticide science and organic chemistry, and discloses a thiazole bisamide compound, a preparation method and an application thereof, the compound has the structure as shown in the formula (I), wherein R1 is H, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl or 3,4,5-trifluorophenyl; R2 is H, methyl, n-propyl or benzyl; R3 is a substituted or unsubstituted diphenyl ether group, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl or phenyl. The novel compound disclosed by the invention can be used as a high-activity cytochrome bc1 compound inhibitor and has certain bactericidal activity.

Description

technical field [0001] The invention relates to the fields of pesticide science and organic chemistry, in particular to a novel thiazole bisamide compound and its preparation method and application. Background technique [0002] mitochondrial cytochrome bc 1 The complex, also called cytochrome c reductase, also known as mitochondrial respiratory chain complex III, is an important part of the mitochondrial and most bacterial respiration electron transport chains, and catalyzes the transfer of electrons from ubiquinone to cytochrome c (bacterial cytochrome c 2 ) reaction is one of the most promising agricultural fungicide targets. [0003] cytochrome bc 1 Compound-targeted fungicides have become the most important type of fungicides at present, and are the research hotspots of major pesticide companies. However, such fungicides have serious resistance problems due to long-term use. Therefore, a cytochrome bc with novel structure and high activity was designed and synthesi...

Claims

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Application Information

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IPC IPC(8): C07D277/56A01N43/78A01P3/00
CPCA01N43/78C07D277/56
Inventor 杨光富陈宬沈艳青熊茂钱
Owner HUAZHONG NORMAL UNIV
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