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(2-oxo-benzothiazole)-3-diacetyl hydrazone compound as well as preparation method and application thereof

A technology of benzothiazole and oxo generation, applied in the direction of botany equipment and methods, applications, chemicals for biological control, etc., can solve problems such as structure and preparation method that have not been reported, and achieve good insecticide and sterilization Active, easy to prepare effects

Active Publication Date: 2011-04-06
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The (2-oxobenzothiazole)-3-acetylhydrazone compound designed and synthesized by the present invention has no report on its structure, preparation method and its research as insecticide and bactericide

Method used

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  • (2-oxo-benzothiazole)-3-diacetyl hydrazone compound as well as preparation method and application thereof
  • (2-oxo-benzothiazole)-3-diacetyl hydrazone compound as well as preparation method and application thereof
  • (2-oxo-benzothiazole)-3-diacetyl hydrazone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 (2-oxobenzothiazole)-3-acetylhydrazone compound I-1 (R 1 = Methyl, R 2 =Methyl) Synthesis

[0027] 2.25 g (10 mmol) (2-oxobenzothiazole)-3-acetylhydrazine and 0.58 g (10 mmol) acetone were dissolved in 20 mL of absolute ethanol, stirred to dissolve, heated to 78° C., and reacted under reflux for 1 hour. Following TLC tracking, the reaction was completed, the reaction solution was cooled and filtered, and the filter cake was recrystallized with 15 mL of ethyl acetate to obtain 2.39 g of white crystals, namely compound I-1. The melting point is 243~245°C and the yield (calculated as (2-oxobenzothiazole)-3-acetylhydrazine, the same below) is 90.7%.

[0028]

[0029] 1 The H NMR and IR spectrum analysis are as follows:

[0030] 1 H NMR(CDCl 3 )δ: 1.83(s, 3H, -CCH 3 CH 3 ), 2.04(s, 3H, -C CH 3 CH 3 ), 5.06(s, 2H, -CH 2 -), 6.91~7.44 (m, 4H, -Ph), 8.83 (s, 1H, -NH-);

[0031] IR v(cm -1 ): 3453, 3191, 3041, 1679, 1596, 1550, 1476, 1412, 1332, 1306, 1276, 1223, 1187, 10...

Embodiment 2

[0032] Example 2 (2-oxobenzothiazole)-3-acetylhydrazone compound I-2 (R 1 = Methyl, R 2 = Ethyl) Synthesis

[0033] Dissolve 2.25 g (10 mmol) (2-oxobenzothiazole)-3-acetylhydrazine and 1.08 g (15 mmol) butanone in 30 mL of absolute ethanol, stir to dissolve, heat to 78°C, and react under reflux for 1.5 hours. After the reaction was completed, the reaction solution was cooled and filtered, and the filter cake was recrystallized with 15 mL of petroleum ether to obtain 2.42 g of white crystals, namely compound 1-2. The melting point is 170-172°C, and the yield is 87.3%.

[0034]

[0035] 1 The H NMR and IR spectrum analysis are as follows:

[0036] 1 H NMR(CDCl 3 )δ: 1.14(t, 3H, J=7.5Hz, -CH 2 CH 3 ), 1.83(s, 3H, = C CH 3 C 2 H 5 ), 2.32~2.36(q, 2H, = CCH 3 CH 2 CH 3 ), 5.08(s, 2H, -CH 2 -), 6.92~7.47 (m, 4H, -Ph), 8.52 (s, 1H, -NH-);

[0037] IR v(cm -1 ): 3454, 3203, 3042, 2939, 1695, 1670, 1555, 1476, 1415, 1374, 1266, 1224, 1189, 1042, 986, 748.

Embodiment 3

[0038] Example 3 (2-oxobenzothiazole)-3-acetylhydrazone compound I-3 (R 1 = Methyl, R 2 =Phenyl) Synthesis

[0039] 2.25g (10mmol) (2-oxobenzothiazole)-3-acetylhydrazine and 1.32g (11mmol) of acetophenone were dissolved in 40mL of absolute ethanol, stirred to dissolve, heated to 78°C, and reacted under reflux for 2.5 hours. After the reaction was completed, the reaction solution was cooled and filtered, and the filter cake was recrystallized with 20 mL of n-hexane to obtain 2.80 g of white crystals, namely compound I-3. The melting point is 244-245°C, and the yield is 86.0%.

[0040]

[0041] 1 The H NMR and IR spectrum analysis are as follows:

[0042] 1 H NMR(CDCl 3 )δ: 2.20(s, 3H, =CPh CH 3 ), 5.23(s, 2H, -CH 2 -), 6.94~7.77 (m, 9H, -Ph), 9.12 (s, 1H, -NH-);

[0043] IR v(cm -1 ): 3451, 3192, 3036, 1694, 1663, 1556, 1474, 1420, 1366, 1333, 1265, 1235, 1178, 1103, 992, 763.

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Abstract

The invention discloses a (2-oxo-benzothiazole)-3-diacetyl hydrazone compound as shown in formula (I) as well as a preparation method and application thereof. The preparation method comprises the following steps: adding (2-oxo-benzothiazole)-3-acethydrazide as shown in formula (II) and ketone as shown in formula (III) in an absolute ethyl alcohol solvent, stirring and heating to 78 DEG C, performing refluxing reaction for 1-5h, tracking the reaction by a thin layer chromatography, postprocessing the reaction solution after the reaction is finished to obtain the compound as shown in formula (I), wherein the compound has good insecticidal and bacteriostatic activity, and can be utilized as an insecticide and a bactericidal agent.

Description

(1) Technical field [0001] The invention relates to a (2-oxobenzothiazole)-3-acetylhydrazone compound and a preparation method and application thereof. (2) Background technology [0002] In recent years, due to the long-term use of insecticides and disinfectants, disease and insect pests have developed resistance, so it has become difficult to use existing insecticides and disinfectants for control. Therefore, it is very urgent to develop new-type insecticides and disinfectants or precursors. [0003] Because heterocyclic compounds (especially fused heterocyclic compounds) have a wide range of biological activities, coupled with their low toxicity, high efficiency, and environmental friendliness, they have become a hot spot for pesticide development today. As an important member of fused heterocyclic compounds, benzothiazole and its derivatives have a wide range of pesticide biological activities, and they have also received great attention in the creation of new pesticides and st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/68A01N43/78A01P7/04A01P7/02A01P3/00
Inventor 翁建全刘会君高宗锦刘幸海谭成侠曹耀艳
Owner ZHEJIANG UNIV OF TECH
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