A kind of cyanofluoroamide compound with antibacterial activity and its preparation method and application

A technology of cyanofluoramide and antibacterial activity, which is applied in the field of chemical synthesis of drugs, can solve the problems of decreased efficacy of fungicides, and achieve excellent bactericidal and antibacterial effects

Active Publication Date: 2020-07-31
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, under normal circumstances, continuous use of the same fungicide for many years will result in a decline in the efficacy of the fungicide

Method used

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  • A kind of cyanofluoroamide compound with antibacterial activity and its preparation method and application
  • A kind of cyanofluoroamide compound with antibacterial activity and its preparation method and application
  • A kind of cyanofluoroamide compound with antibacterial activity and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the synthesis of compound 2-(2-cyanophenoxy)-2-fluoro-N-methyl-N-phenylacetamide (6a)

[0031]

[0032] 2-(2-cyanophenoxy)-2-fluoroacetic acid was prepared by referring to the method disclosed in literature (Nature, 2014, 507, 215–220.).

[0033] 2-(2-cyanophenoxy)-2-fluoroacetic acid (compound 4), N-methylaniline, DCC (dicyclohexylcarbodiimide) and 4-DMAP (4-dimethylaminopyridine) , according to the molar ratio of 1:1.2:1.1:0.2 into the reaction flask, the amount of compound 4 is 1.5mmol. The reaction system was stirred and reacted in DCM solvent (dichloromethane) at room temperature for 16 hours. After the reaction, cool down, filter under reduced pressure with a short silica gel column, and rotate the filtrate to remove the solvent. The residue is chromatographed on a silica gel column, rinsed with PE:EtOAc=1:1 developer, detected by TLC, and the effluents containing the product are combined. solution, the solvent was distilled off by a rotary evap...

Embodiment 2

[0036] Example 2: Synthesis of compound 2-(2-cyanophenoxy)-2-fluoro-N-phenylacetamide (6b).

[0037] The synthesis method was the same as in Example 1, and 2-(2-cyanophenoxy)-2-fluoroacetic acid was reacted with aniline to obtain light yellow solid compound (6b) with a yield of 86%.

[0038]

[0039] Compound (6b) NMR analysis data are as follows:

[0040] 1 H NMR (600MHz, CDCl 3 )δ8.56(s,1H),7.78–7.56(m,4H),7.42–7.33(m,3H),7.30(t,J=7.6Hz,1H),7.19(t,J=7.4Hz,1H ),6.08(d,J=59.0Hz,1H). 13 C NMR (151MHz, CDCl 3 )δ160.4(d,J C-F =25.5Hz,1C),156.7(d,J C-F =2.7Hz,1C),136.3,135.0,133.6,129.2,125.5,125.0,120.1,116.2,115.7,104.1,103.1(d,J C-F =236.6Hz,1C).

Embodiment 3

[0041] Example 3: Synthesis of compound N-(2-bromophenyl)-2-(2-cyanophenoxy)-2-fluoroacetamide (6c).

[0042] The synthesis method was the same as that in Example 1, and 2-(2-cyanophenoxy)-2-fluoroacetic acid was reacted with 2-bromoaniline to obtain light yellow solid compound (6c), with a yield of 63%.

[0043]

[0044] Compound (6c) NMR analysis data are as follows:

[0045] 1 H NMR (600MHz, CDCl 3 )δ8.89(s,1H),8.37(dd,J=8.2,1.4Hz,1H),7.71–7.63(m,2H),7.59(dd,J=8.0,1.3Hz,1H),7.39–7.32 (m,2H),7.29(t,J=7.6Hz,1H),7.07(td,J=7.9,1.5Hz,1H),6.18(d,J=59.0Hz,1H). 13 C NMR (151MHz, CDCl 3 )δ160.5(d,J C-F =25.3Hz,1C),156.1(d,J C-F =2.6Hz,1C),134.8,134.2,134.1,132.6,128.4,126.5,124.9,122.1,116.0,115.1,114.4,104.2,103.0(d,J C-F =237.3Hz,1C).

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Abstract

The invention belongs to the field of chemical synthesis medicine, and particularly relates to a tetraniliprole compound with antibacterial activity as well as a preparation method and application thereof. The structure formula of the tetraniliprole compound with antibacterial activity is shown as the following formula, wherein R1 is H or F; R2 is H or alkyls of C1-C12; R3 is substitutional-group-free or F, Cl, Br, methyl, -CH2OH, CO2Et or NO2-containing or ester group substituted aromatic ring, pyridine, pyrimidine, thiazole or parazole. The tetraniliprole compound has the inhibition activityon penicillum italicum, gibberella saubinetii, gloeosporium musarum, lychee anthrax, tomato blight and magnaporthe oryzae. The tetraniliprole compound provided by the invention has good sterilizationand antibacterial activity. The formula is shown in the description.

Description

technical field [0001] The invention belongs to the field of chemically synthesized drugs, and in particular relates to a cyanofluoroamide compound with antibacterial activity, a preparation method and application thereof. Background technique [0002] Amide fungicides are an ancient class of fungicides, which account for a considerable proportion of fungicides, accounting for about a quarter of all fungicides. These compounds have been used as fungicides for nearly fifty years, and there have been reports of novel structures. Numerous research results have shown that amide antibacterial agents mainly inhibit the growth of pathogenic bacteria and eventually lead to their death by affecting the respiratory chain electron transport system of pathogenic bacteria. Nippon Pesticide Co., Ltd. has developed Flutolanil containing trifluoromethyl. Flutolanil is a systemic fungicide used to prevent diseases caused by certain basidiomycete fungi and rice caused by Rhizoctonia Sheath ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/54C07D213/75C07D239/42C07D231/40C07D277/46C07D277/56A01N37/36A01N43/40A01N43/54A01N43/56A01N43/78A01P3/00
CPCA01N37/36A01N43/40A01N43/54A01N43/56A01N43/78C07C255/54C07D213/75C07D231/40C07D239/42C07D277/46C07D277/56
Inventor 汤日元邓建超林非徐莉朱柱
Owner SOUTH CHINA AGRI UNIV
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