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Tetraniliprole compound with antibacterial activity as well as preparation method and application thereof

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: 2018-09-04
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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  • Tetraniliprole compound with antibacterial activity as well as preparation method and application thereof
  • Tetraniliprole compound with antibacterial activity as well as preparation method and application thereof
  • Tetraniliprole compound with antibacterial activity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Synthesis of compound 2-(2-cyanophenoxy)-2-fluoro-N-methyl-N-phenylacetamide (6a)

[0031]

[0032] Refer to the method disclosed in the literature (Nature, 2014, 507, 215-220.) to prepare 2-(2-cyanophenoxy)-2-fluoroacetic acid.

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

Embodiment 2

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

[0037] The synthesis method is the same as in Example 1. The reaction between 2-(2-cyanophenoxy)-2-fluoroacetic acid and aniline yields a pale yellow solid compound (6b) with a yield of 86%.

[0038]

[0039] The NMR analysis data of compound (6b) 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 is the same as in Example 1. The reaction of 2-(2-cyanophenoxy)-2-fluoroacetic acid and 2-bromoaniline to obtain a pale yellow solid compound (6c) with a yield of 63%.

[0043]

[0044] The NMR analysis data of compound (6c) 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 = 7.6 Hz, 1H), 7.07 (td, J = 7.9, 1.5 Hz, 1H), 6.18 (d, J = 59.0 Hz, 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 specifically relates to a cyanofluoroamide compound with antibacterial activity and a preparation method and application thereof. Background technique [0002] Amide fungicides are an ancient type of fungicides, and their quantity occupies a considerable proportion of the fungicides, accounting for about a quarter of all fungicides. Such compounds have been used as fungicides for nearly 50 years, and there have been reports of varieties with novel structures. Numerous research results indicate that amide antibacterial agents mainly affect the electron transport system of the respiratory chain of pathogenic bacteria, thereby inhibiting the growth of pathogenic bacteria and ultimately leading to their death. Japan Pesticide Co., Ltd. has developed Flutolanil containing trifluoromethyl. Flutolanil is a systemic fungicide used to prevent diseases caused by certain Basidiomycetes and rice c...

Claims

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Application Information

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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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