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N'-substituted benzal-1,2,3,4-tetrahydroquinoline base-1-(sulfo)hydrazide compound and preparation method and application thereof

A compound, phenoxy technology, applied in the field of pathogenic bacteria control, achieves obvious inhibitory effect, broad-spectrum bactericidal activity, and novel structure effect

Inactive Publication Date: 2015-11-11
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report of introducing 1,2,3,4-tetrahydroquinoline, a natural product active fragment with excellent biological activity, into its skeleton structure. Therefore, the present invention discloses a class of novel N'-substituted Benzylidene-1,2,3,4-tetrahydroquinolinyl-1-(thio)hydrazide compound and its preparation method and application as agricultural fungicide

Method used

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  • N'-substituted benzal-1,2,3,4-tetrahydroquinoline base-1-(sulfo)hydrazide compound and preparation method and application thereof
  • N'-substituted benzal-1,2,3,4-tetrahydroquinoline base-1-(sulfo)hydrazide compound and preparation method and application thereof
  • N'-substituted benzal-1,2,3,4-tetrahydroquinoline base-1-(sulfo)hydrazide compound and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0025] Add 0.96g (5mmol) of 1,2,3,4-tetrahydroquinolinyl-1-carboxylhydrazide, 0.58g (5.5mmol) of benzaldehyde, and 10mL of absolute ethanol into a 25mL single-necked bottle, and stir at room temperature for 30 minutes. After the reaction was completed, it was suction-filtered and washed with ethanol to obtain 0.94 g of white solid with a yield of 67.2%. The appearance and melting point of this white solid product are shown in Table 1, 1 HNMR spectrum data are shown in Table 2.

Embodiment 2

[0027] Add 0.96g (5mmol) of 1,2,3,4-tetrahydroquinolinyl-1-carboxylhydrazide, 0.63g (6mmol) of benzaldehyde, and 10mL of anhydrous methanol into a 25mL single-necked bottle, and stir at 0°C for 60 minutes. After the reaction was completed, it was filtered with suction and washed with methanol to obtain 0.84 g of white solid with a yield of 59.7%. The appearance and melting point of this white solid product are shown in Table 1, 1 HNMR spectrum data are shown in Table 2.

[0028] According to the same method as above for the preparation of compound I-01, only R in formula III is replaced by various substituents, and reacted with the compound shown in formula II to obtain the corresponding products I-02 ~ I-30, the appearance of the compound, Melting point and yield are listed in Table 1, 1 HNMR spectral data are listed in Table 2.

[0029] Preparation of compound N'-(3-methylbenzylidene)-1,2,3,4-tetrahydroquinolinyl-1-thiocarbohydrazide (I-31)

[0030]

Embodiment 3

[0032] In a 25mL single-necked bottle, add 0.41g (2mmol) 1,2,3,4-tetrahydroquinolyl-1-thiocarbohydrazide, 0.26g (2.2mmol) 3-methylbenzaldehyde, 5mL absolute ethanol , stirred at room temperature for 30 minutes. After the reaction was completed, it was suction filtered and washed with ethanol to obtain 0.39 g of a yellow solid with a yield of 62.9%. The appearance and fusing point of this product are shown in Table 1, 1 HNMR spectrum data are shown in Table 2.

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Abstract

The invention belongs to the technical field of pathogenic bacterium control, and particularly relates to an N'-substituted benzal-1,2,3,4-tetrahydroquinoline base-1-(sulfo)hydrazide compound and a preparation method and application thereof. By substituting 1,2,3,4-tetrahydroquinoline fragments excellent in biological activity into a substituted benzaldehyde thiosemicarbazone compound, the N'-substituted benzal-1,2,3,4-tetrahydroquinoline base-1-(sulfo)hydrazide compound novel in structure is obtained. The structure of the compound is seen in the formula I (please see the formula in the specification). The preparation method is easy to operate and free of harmful by-products, and raw materials are easy to obtain. The compound has broad-spectrum bactericidal activity, particularly has an obvious restraining effect on Valsa mali, rhizoctonia solani and gaeumannomyces gramini, and can be used as a bactericide for preventing and curing plant diseases.

Description

technical field [0001] The invention belongs to the technical field of pathogenic bacteria control, and specifically relates to N'-substituted benzylidene-1,2,3,4-tetrahydroquinolyl-1-(thio)hydrazide compounds and their preparation methods and applications. Background technique [0002] The growing population urgently needs more food supply, and reducing the production reduction of food crops caused by diseases, insects, and weeds is a more effective means to increase food production. To achieve this purpose, the most effective method at present is the use of chemical pesticides. 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. [0003] Tetrahydroquinoline widely exists in natural plants, and its derivatives have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/08A01N47/34A01P3/00
CPCA01N47/34C07D215/08
Inventor 凌云雷鹏杨新玲徐焱张学博张小河徐高飞
Owner CHINA AGRI UNIV
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