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Aryl substituted thiosemicarbazone compound and preparation method and application thereof

A technology of thiosemicarbazones and compounds, which is applied in the field of aryl-substituted thiosemicarbazones and their preparation, and can solve the problem of less thiosemicarbazones

Active Publication Date: 2019-05-07
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] But, the kind of thiosemicarbazone compounds with above-mentioned activity is less, therefore, it is necessary to develop a kind of effective thiosemicarbazone compounds

Method used

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  • Aryl substituted thiosemicarbazone compound and preparation method and application thereof
  • Aryl substituted thiosemicarbazone compound and preparation method and application thereof
  • Aryl substituted thiosemicarbazone compound and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0048] Embodiment 1, the preparation of aryl-substituted thiosemicarbazone compound I-07

[0049]

[0050] Weigh aldehyde (0.33g, 1.19mmol) and dissolve it in 10mL of absolute ethanol, add thiosemicarbazide (0.11g, 1.19mmol) to the aldehyde, and add 2 drops of glacial acetic acid as a catalyst, stir at room temperature (25°C) until the raw material The reaction was complete (12 hours of reaction). Purified by filtration, washed with ethanol, collected solid, and dried to obtain 0.37 g of white solid. Yield 90.4%. 1H NMR(300MHz,DMSO)δ11.24(s,1H),8.19(s,1H),7.72(d,J=9.8Hz,1H),7.65(s,1H),7.55(d,J=8.4Hz , 2H), 7.44 (d, J = 8.6Hz, 2H), 7.33–7.20 (m, 4H), 6.80 (d, J = 9.8Hz, 1H).

[0051] According to the same method as the above preparation of compound I-07, only R1 and R5 in formula I are replaced with the corresponding substituents as shown in Table 1 to obtain products I-01 ~ I-11, I- 15 to I-20.

Embodiment 2

[0052] Embodiment 2, the preparation of aryl-substituted thiosemicarbazone compound I-14

[0053]

[0054] Aldehyde (0.94g, 2mmol) was dissolved in 10mL of absolute ethanol and added to a 50mL three-necked flask, thiosemicarbazide (0.19g, 2mmol) was added to the reaction solution, 3 drops of glacial acetic acid were added dropwise, and stirred at room temperature (25°C) for 12 Hour. Filtration, 0.95 g of white solid after drying, yield 88%. 1H NMR(300MHz,DMSO)δ11.16(s,1H),8.09(s,1H),7.72(d,J=9.8Hz,1H),7.54(s,1H),7.19–7.11(m,2H) ,7.09–7.01(m,2H),6.94–6.86(m,2H),6.85–6.77(m,2H),6.59(d,J=9.8Hz,1H),0.94(d,18H),0.20(d ,12H).

Embodiment 3

[0055] Embodiment 3, the preparation of compound 1-12

[0056]

[0057] Preparation of Intermediate 1:

[0058] Dissolve TBS aldehyde (1.11 g, 2.36 mmol) in 10 mL of tetrahydrofuran, and stir in an ice-salt bath. Tetrabutylammonium fluoride (5 mL, 5 mmol, 1 M) was added dropwise to the reaction solution in an ice-salt bath. With the addition of tetrabutylammonium fluoride, the reaction solution began to turn black, and finally the color turned brownish yellow. React in an ice bath for 2 hours, add 7 mL of water for post-treatment, then add 10 mL of 10% aqueous sodium bicarbonate solution, extract with a separatory funnel, and collect chloroform (3×40 mL) to collect the organic phase. After desolvation under reduced pressure, it was purified by column using ethyl acetate as the eluent to obtain 0.52 g of yellow liquid with a yield of 100%.

[0059] Preparation of target compound I-12:

[0060] Intermediate 1 (0.52g, 2.36mmol) was dissolved in 5mL ethanol and added to a 2...

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Abstract

The invention discloses an aryl-substituted thiosemicarbazone compound and a preparation method and application thereof. The structural formula of the compound is as shown in Formula I. The preparation method comprises the steps of: mixing a compound of the formula II and a compound of the formula III in an organic solvent to carry out a condensation reaction to obtain the compound of the formulaI. A salt of the aryl-substituted thiosemicarbazone compound is obtained by reacting the aryl-substituted thiosemicarbazone compound with an acid. The compound and the salt thereof are used in the preparation of a medicament for controlling phytopathogen which is harmful to agricultural production or controlling the phytopathogen which is harmful to agricultural production. The compound has novelstructure and simple preparation method, and has a broad spectrum of bactericidal activity.

Description

technical field [0001] The invention relates to an aryl-substituted thiosemicarbazone compound, a preparation method and application thereof, and belongs to the technical field of pathogenic bacteria control. Background technique [0002] The extensive use of pesticides has reduced the loss of agricultural products caused by pests and weeds, and has made outstanding contributions to ensuring the quality and safety of agricultural products and reducing the labor intensity of farmers. However, the wide-scale use of pesticides inevitably produces a series of problems such as drug resistance and ecological environment pollution. Therefore, it is urgent to develop new green pesticides with high efficiency, broad spectrum and environmental friendliness to replace the existing pesticide varieties. Thiosemicarbazone compounds are important intermediates of organic synthetic drugs, which have a wide range of physiological activities such as antibacterial, antiviral, antitumor, insec...

Claims

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Application Information

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IPC IPC(8): C07C337/08C07F7/18A01N47/34A01N55/10A01P3/00
Inventor 凌云张学博杨新玲孙腾达马航宇张晓鸣
Owner CHINA AGRI UNIV
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