(S)-1,3-thiazolyl phenyl furan thioformate compounds and preparation method and application thereof

A technology of thiazolylphenylfuranthiocarboxylic acid and ester compounds, which is applied in the field of preparation of heterocyclic compounds, to achieve the effects of reducing pathogenicity, reducing drug resistance, and delaying drug resistance

Active Publication Date: 2019-10-01
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 rese

Method used

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  • (S)-1,3-thiazolyl phenyl furan thioformate compounds and preparation method and application thereof
  • (S)-1,3-thiazolyl phenyl furan thioformate compounds and preparation method and application thereof
  • (S)-1,3-thiazolyl phenyl furan thioformate compounds and preparation method and application thereof

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 (S)-1,3-thiazolyl phenyl furan thioformate compounds and a preparation method and application thereof. The compounds have a strong inhibitory effect on a hpa1 gene promoter ina pathogen T3SS system, and the inhibition rate of some compounds exceeds 97%, and the compounds can be used as a T3SS system inhibitor; some of the compounds strongly inhibit the plant pathogen T3SSsystem, does not affect the growth of plant pathogenic bacteria meanwhile, but only significantly reduces the pathogenicity of the plant pathogenic bacteria to achieves the prevention and/or treatmentof plant diseases caused by the plant pathogenic bacteria; the compounds can be used as a plant pathogen type III secretion system inhibitor, or used for preparing a drug for related the plant diseases for preventing and/or treating the plant diseases, also have the effect of reducing and delaying the resistance of the plant pathogenic bacteria to the compounds, and have a longer effective life for prevention and/or treatment of the plant diseases and broad application prospects..

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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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
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