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Compound having isothiazolinone and N-arylpyrazole structure and preparation method and application thereof

A technology for isothiazolinone and benzisothiazolinone sodium salt, which is applied to compounds with isothiazolinone and N-arylpyrazole structures and their preparation and application fields, and achieves simple and convenient reaction operation and reaction yield. High and good biological activity

Active Publication Date: 2019-02-12
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And most of them are easy to photolyze under natural conditions to produce low-toxic substances

Method used

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  • Compound having isothiazolinone and N-arylpyrazole structure and preparation method and application thereof
  • Compound having isothiazolinone and N-arylpyrazole structure and preparation method and application thereof
  • Compound having isothiazolinone and N-arylpyrazole structure and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] 2-(Benzisothiazoline-3-oxyl)-N-(3-cyano-1-phenylpyrazol-5-yl)acetamide

[0029] In a 100mL four-neck flask, 3-cyano-5-amino-1-phenylpyrazole chloroacetamide and benzisothiazolinone sodium salt were dissolved in the organic solvent DMF according to the molar ratio of 1:1.1, and a small amount of potassium iodide was added As a catalyst, react in an oil bath at 100°C for 5h. After the reaction, the solvent was concentrated, poured into water, a large amount of solids precipitated, suction filtered, washed, and dried to obtain a crude product. Column chromatography (ethyl acetate:petroleum ether=1:1.2) gave the target product 2-(benzoiso Thiazolin-3-oxy)-N-(3-cyano-1-phenylpyrazol-5-yl)acetamide. Yield: 72%. Melting point: 155-157°C. The structural formula and spectrum analysis of the product are as follows:

[0030]

[0031] 1 H NMR (CDCl 3 ,500MHz)δ:5.15(s,2H,CH 2 ),7.15(s,1H,C–H),7.08~7.88(m,9H,Ar–H), 8.60(s,1H,N–H);

[0032] IR(KBr) v: 3177(N–H), 3058(C–H), ...

Embodiment 2

[0038] 2-(Benzisothiazolin-3-oxyl)-N-(3-cyano-1-(2-methoxyphenyl)pyrazol-5-yl)acetamide:

[0039] In a 100mL four-necked flask, 3-cyano-5-amino-1-2-methoxyphenylpyrazole chloroacetamide and benzisothiazolinone sodium salt were dissolved in the organic solvent DMF at a molar ratio of 1:1.4 , add a small amount of potassium iodide as a catalyst, and react in an oil bath at 100°C for 5h. After the reaction, the solvent was concentrated and poured into water. A large amount of solids precipitated out. Suction filtration, washing, and drying gave the crude product. Column chromatography (ethyl acetate:petroleum ether=1:1.3) gave the target product. Yield: 70%. Melting point: 152-154°C. The structural formula and spectrum analysis of the product are as follows:

[0040]

[0041] 1 H NMR (CDCl 3 ,500MHz)δ:3.84(s,3H,CH 3O),5.17(s,2H,CH 2 ),7.14(s,1H,C–H),6.78~7.87 (m,8H,Ar–H),8.31(s,1H,N–H);

[0042] IR(KBr) v: 3295(N–H), 3170(C–H), 2241(C≡N), 1713(C=O), 1596(C=N), 1557(C=C...

Embodiment 3

[0048] 2-(Benzisothiazolin-3-oxyl)-N-(3-cyano-1-(4-methoxyphenyl)pyrazol-5-yl)acetamide:

[0049] In a 100mL four-neck flask, 3-cyano-5-amino-1-p-benzyloxypyrazole chloroacetamide and benzisothiazolinone sodium salt were dissolved in the organic solvent DMF at a molar ratio of 1:1.1, Add a small amount of potassium iodide as a catalyst, and react for 5 hours in an oil bath at 100°C. After the reaction, the solvent was concentrated and poured into water. A large amount of solids precipitated out. Suction filtration, washing, and drying gave the crude product. Column chromatography (ethyl acetate:petroleum ether=1:1.2) gave the target product. Yield: 68%. Melting point: 171-172°C. The structural formula and spectrum analysis of the product are as follows.

[0050]

[0051] 1 H NMR (CDCl 3 ,500MHz)δ:3.85(s,3H,CH 3 O),5.14(s,2H,CH 2 ),6.99(s,1H,C–H),7.01~7.82(m,8H,Ar–H),8.34(s,1H,N–H);

[0052] IR(KBr) v: 3383(N–H), 3167(C–H), 2241(C≡N), 1717(C=O), 1597(C=N), 1557(C=C),...

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Abstract

The invention discloses a compound having an isothiazolinone and N-arylpyrazole and a preparation method and application thereof. The method for preparing the compound having the isothiazolinone and N-arylpyrazole structure according to the invention comprises the following steps: enabling a compound represented by the formula (II) to react with a benzisothiazolone sodium salt in an organic solvent by using potassium iodide as a catalyst in an oil bath at a temperature of 100 to 105 DEG C for 4.5 to 5 h; after the reaction is completed, concentrating a solvent, pouring into water, precipitating a large amount of solid, performing suction filtration, washing, drying to obtain a crude product, and obtaining a target product of the formula (I) by column chromatography. The compound disclosedby the invention is a compound having the isothiazolinone and N-arylpyrazole structure, has good biosuppressive activity, has good biological activity in sterilizing, controlling algae and killing mollusc, has a certain corrosion inhibition effect, and has broad application prospects in seawater circulating cooling water. The formula (I) is shown in the specification.

Description

technical field [0001] The invention relates to a compound with isothiazolinone and N-arylpyrazole structures, a preparation method and application thereof. Background technique [0002] Since pyrazole exists in many natural products, it has high efficiency, low toxicity, certain hydrophilicity, and the variability of substituents on the pyrazole ring, especially N-arylpyrazole, is widely used in the fields of medicine and pesticides. play a very important role. At the same time, people have gradually found that pyrazole compounds containing two N have good corrosion inhibition effect on copper. [0003] Most of the pyrazole compounds have biological activity, are widely used in pesticides, medicine, etc., and have broad research prospects. And most of them are easy to photolyze under natural conditions to produce low-toxic substances. [0004] In the application of antibacterial aspects, the currently commercialized pyrazole antibacterial agents include: Maoyening, Luyen...

Claims

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Application Information

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IPC IPC(8): C07D417/12A01N43/80A01P1/00A01P3/00A01P9/00A01P13/00C02F1/50C02F103/02
CPCA01N43/80C02F1/50C07D417/12C02F2103/023C02F2303/08
Inventor 于鹏潘建刘璧铭徐炎华
Owner NANJING UNIV OF TECH
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