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3,4(6)-disubstitued-1,3-benzoxazine-2-ketone compound with bactericidal acitivity

A ketone compound and benzoxazine technology, applied in the field of pesticides, can solve the problems of few studies on agricultural bactericidal activity and no reports, and achieve the effect of simple synthesis method and good bactericidal activity

Inactive Publication Date: 2014-09-17
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Based on the above research background, it has been fully demonstrated that 1,3-benzoxazin-2-one and its derivatives have a wide range of biological activities, but as far as we know, the above-mentioned compounds are mainly for medical bactericidal and anticancer activities, while There are very few studies on the fungicidal activity in agriculture, and there are almost no reports

Method used

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  • 3,4(6)-disubstitued-1,3-benzoxazine-2-ketone compound with bactericidal acitivity
  • 3,4(6)-disubstitued-1,3-benzoxazine-2-ketone compound with bactericidal acitivity
  • 3,4(6)-disubstitued-1,3-benzoxazine-2-ketone compound with bactericidal acitivity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: 6-Methyl-3-phenyl-3,4-2 H Synthesis of -1,3-Benzoxazin-2-one

[0035] Add 0.426g of 4-methyl-2-((anilino)methyl)phenol into a 100 mL round bottom flask, add 40 mL of solvent tetrahydrofuran, dropwise add 0.606 g of triethylamine, and slowly drop 10 mL of tetrahydrofuran solution containing 0.300 g of triphosgene was reacted at room temperature for 30 min, and then the reaction system was transferred to an oil bath and heated to 60 °C for 2 h. After the reaction was complete (TLC detection), 10 mL of ethyl acetate was added, and suction filtered. The filter cake was washed with ethyl acetate, desolvated under reduced pressure, separated and purified by column chromatography to obtain a white solid, yield: 91.0%. Melting point: 158.7-159.27°C.

[0036] 1 H NMR (CDCl 3 , 500 MHz) δ: 7.43-7.46 (m, 2H), 7.38-7.40 (m, 2H), 7.30-7.33 (m, 1H), 7.11 (d, J=10 Hz, 1H), 7.01 (d, J =10 Hz, 1H), 6.93 (s, 1H), 4.79 (s, 2H), 2.33 (s, 3H)

[0037] 13 C NMR (CDCl 3 , ...

Embodiment 2

[0039] Example 2: 6-methyl-3-(2-methoxyphenyl)-3,4-2 H Synthesis of -1,3-Benzoxazin-2-one

[0040] Add 0.365g of 4-methyl-2-((2-methoxyanilino)methyl)phenol into a 100 mL round-bottomed flask, add 40 mL of solvent tetrahydrofuran, add dropwise 0.455 g of triethylamine, and place in an ice bath Slowly add 10 mL of tetrahydrofuran solution containing 0.222 g of triphosgene dropwise, react at room temperature for 30 min, then transfer the reaction system into an oil bath and heat to 60 °C for 2 h, after the reaction is complete (TLC detection), add ethyl acetate 10 mL, suction filtered, the filter cake was rinsed with ethyl acetate, desolvated under reduced pressure, separated and purified by column chromatography to obtain a white solid, yield: 79.8%. Melting point: 182.8-184.0°C.

[0041] 1 H NMR (CDCl 3 , 500 MHz) δ: 7.35 (td, J 1 =1.5 Hz, J 2 =8 Hz, 1H), 7.31 (dd, J 1 =1.5 Hz, J 2=8 Hz , 7.09 (d, J=5 Hz, 1H), 6.99-7.03 (m, 3H), 6.89 (s, 1H), 4.71 (d, J=3.5 Hz, 2H), ...

Embodiment 3

[0044] Example 3: 6-methyl-3-(3-methylphenyl)-3,4-2 H Synthesis of -1,3-Benzoxazin-2-one

[0045] Add 0.341 g of 4-methyl-2-((3-methylanilino)methyl)phenol into a 100 mL round-bottomed flask, add 40 mL of solvent tetrahydrofuran, and dropwise add 0.455 g of triethylamine. , slowly drop 10 mL of tetrahydrofuran solution containing 0.222 g of triphosgene, react at room temperature for 30 min, then transfer the reaction system into an oil bath and heat to 60 °C for 2 h, after the reaction is complete (TLC detection), add 10 mL of ethyl acetate, After suction filtration, the filter cake was rinsed with ethyl acetate, desolvated under reduced pressure, separated and purified by column chromatography to obtain a white solid with a yield of 89.5%. Melting point: 133.2-134.3°C.

[0046] 1 H NMR (CDCl 3 , 500 MHz) δ: 7.26 (dd, J 1 =8.5 Hz, J 2 =15.5 Hz, 4H), 7.11 (d, J=8.5 Hz, 1H), 7.0 (d, J=8 Hz, 1H), 6.92 (s, 1H), 4.77 (s, 2H), 2.37 (s, 3H ), 2.33 (s, 3H).

[0047] 13 C NM...

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Abstract

The invention provides a 3,4(6)-disubstituted-1,3-benzoxazine-2-ketone compound shown in a formula (I). In the formula (I), when a substituent group R1 is -CH3 and a substituent group R2 is H, R3 is H, or 3-CH3, or 4-CH3, or 2-OCH3, or 4-Cl; when the substituent group R1 is H and the substituent group R2 is -CH3, R3 is 3-CH3, or 4-CH3, 2-OCH3, or 3-OCH3, or 4-Cl. The 3,4(6)-disubstituted-1,3-benzoxazine-2-ketone compound has good bactericidal activity on pathogenic bacteria of crops. The formula (I) is described in the specification.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to the synthesis of a novel 3,4(6)-disubstituted-1,3-benzoxazin-2-one compound with bactericidal activity and its bactericidal activity. Background technique [0002] Heterocyclic compounds have a wide range of biological activities and have become one of the hot spots in the research of new pesticide creation. 1,3-Benzoxazin-2-one compounds usually have a wide range of biological activities and occupy a very important position in the field of medicine. For example, in 1982, Latif et al reported the synthesis and antibacterial activity of a series of 1,3-benzoxazinone compounds, showing that the compounds were effective against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Bacillus, and Bacillus subtilis , Bacillus cereus, Sarcina luteus, Candida albicans, Aspergillus niger, Aspergillus flavus, Botrytis cinerea, Fusarium oxysporum, etc. exhibited a wide rang...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/18A01N43/86A01P3/00
CPCA01N43/86C07D265/18
Inventor 唐子龙焦文杰王恋颜林
Owner HUNAN UNIV OF SCI & TECH
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