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A kind of (s)-1,3-thiazole phenylfuryl thiocarbamate compound and its preparation method and application

A technology of thiazole phenylfuran thiocarboxylate and ester compounds, which is applied in the field of preparation of heterocyclic compounds, and achieves the effects of broad application prospects, prevention of drug resistance, and long effective service life

Active Publication Date: 2022-01-25
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although there are many studies on heterocyclic compounds at present, such compounds still have unlimited research and development space, and further research can be carried out to develop more application values ​​and prospects

Method used

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  • A kind of (s)-1,3-thiazole phenylfuryl thiocarbamate compound and its preparation method and application
  • A kind of (s)-1,3-thiazole phenylfuryl thiocarbamate compound and its preparation method and application
  • A kind of (s)-1,3-thiazole phenylfuryl thiocarbamate compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of compound III-1

[0036] The specific preparation process of compound III-1 is as follows:

[0037] Add 0.44g 5-(2-chlorophenyl)-2-furancarboxylic acid (2mmol) and 5mL thionyl chloride successively to a 50mL single-necked bottle; heat to reflux for 1.5 hours, stop heating, wait for the reaction solution to cool to room temperature, evaporate under reduced pressure Except the remaining thionyl chloride, the obtained furoyl chloride intermediate is directly used in the next step without purification;

[0038] In another 50 mL three-necked flask, 0.23 g (2.0 mmol) of mercaptothiazole, 0.55 g of potassium carbonate (4.0 mmol), and 20 mL of acetonitrile were sequentially added. Stir at room temperature for half an hour under nitrogen protection; cool to 0°C in an ice bath, slowly add a solution of furoyl chloride in acetonitrile (≈20 mL), and transfer to room temperature for reaction after the addition is complete. Thin-layer chromatography (T...

Embodiment 2

[0042] Embodiment 2: the synthesis of compound III-2

[0043] The method is the same as in Example 1, except that 5-(3-chlorophenyl)-2-furoyl chloride is used instead of 5-(2-chlorophenyl)-2-furoyl chloride to obtain pink solid compound III-2 .

[0044] 1 H NMR (400MHz, Chloroform-d) δ8.00(dd, J=7.9,1.6Hz,1H),7.97(d,J=3.3Hz,1H),7.60(d,J=3.3Hz,1H),7.50 (dd, J=8.0,1.2Hz,1H),7.44(d,J=3.8Hz,1H),7.41(td,J=7.7,1.3Hz,1H),7.35(dd,J=7.5,1.7Hz, 1H), 7.33(d, J=3.8Hz, 1H).

[0045]

Embodiment 3

[0046] Embodiment 3: the synthesis of compound III-3

[0047] The method is the same as in Example 1, except that 5-(4-chlorophenyl)-2-furoyl chloride is used instead of 5-(2-chlorophenyl)-2-furoyl chloride to obtain pink solid compound III-3 .

[0048] 1 H NMR (400MHz, Chloroform-d) δ7.97(d, J=3.3Hz, 1H), 7.77–7.73(m, 2H), 7.60(d, J=3.4Hz, 1H), 7.46–7.43(m, 2H), 7.42(d, J=3.8Hz, 1H), 6.84(d, J=3.8Hz, 1H).

[0049]

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Abstract

The invention discloses a (S)-1,3-thiazole phenylfuryl thiocarbamate compound, a preparation method and an application thereof. The compounds of the present invention have a strong inhibitory effect on the hpa1 gene promoter in the T3SS system of pathogenic bacteria, and the inhibition rate of some compounds exceeds 97%, which can be used as T3SS system inhibitors; wherein some compounds can strongly inhibit the T3SS system of plant pathogens. At the same time, it does not affect the growth of plant pathogenic bacteria, but only significantly reduces the pathogenicity of plant pathogenic bacteria, so as to prevent and / or treat plant diseases caused by plant pathogenic bacteria; the compound can be used as a type III secretion system inhibitor of plant pathogenic bacteria, Or it can be prepared as a medicine for related plant diseases, which is used to prevent and / or treat plant diseases, and also has the effect of reducing and delaying the generation of resistance of plant pathogenic bacteria to the compound, and has a relatively long history in the prevention and / or treatment of plant diseases. The effective service life, the application prospect is broad.

Description

technical field [0001] The present invention relates to the technical field of preparation of heterocyclic compounds, more specifically, to a (S)-1,3-thiazolylphenylfuran thiocarbamate compound and its preparation method and application. Background technique [0002] In recent years, heterocyclic compounds have played an important role in the creation of new ultra-high-efficiency pesticides. When looking for compounds with novel structures and biological activities, designing and synthesizing various heterocyclic compounds is a very important way, among which thiazole compounds have been used. It has become one of the most active heterocyclic compounds in the field of pesticides. Many thiazole pesticides, such as the fungicides thiathiocyanate and thiazil, the insecticides chlorfenapyr, thiazofos, clothianidin, the herbicides thiafenprop, mefenacet, thiazopyr, plant growth Modulators such as thiazolon, thiadizuron, and fluthiazate all occupy an indispensable position in the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12A01N43/78A01P3/00
CPCC07D417/12A01N43/78
Inventor 崔紫宁何敏姜珊李宇豪陈恺宏向绪稳
Owner SOUTH CHINA AGRI UNIV