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N-substituent benzaldehyde thiosemicarbazone derivative and preparation method and application thereof

A technology for benzaldehyde aminosulfide and derivatives, which is applied in botanical equipment and methods, chemicals for biological control, applications, etc. Simple, improved efficacy, enhanced lipid solubility

Inactive Publication Date: 2019-11-29
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, following it, there are also problems such as the abuse of pesticides leading to serious environmental pollution, and the single variety making bacteria resistant to pesticides.

Method used

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  • N-substituent benzaldehyde thiosemicarbazone derivative and preparation method and application thereof
  • N-substituent benzaldehyde thiosemicarbazone derivative and preparation method and application thereof
  • N-substituent benzaldehyde thiosemicarbazone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1. Get 2.5mL (0.02mol) of 4-ethylaniline and dissolve it in a three-necked round-bottomed flask filled with 40mL of 95% ethanol aqueous solution, and add 4.2mL (0.08mol) of 25% concentrated Ammonia, then slowly dropwise added 2.0mL (0.02mol) carbon disulfide, then the reaction mixture was stirred at 30°C for 2 hours, then added 2.3296g (0.02mol) sodium chloroacetate, stirred for 1 hour, then dropwise Add 2.6 mL (0.02 mol) of hydrazine hydrate aqueous solution with a volume concentration of 85%, and stir under reflux for 2 hours. After the reaction is completed, vacuum filter and wash with a large amount of deionized water to remove impurities, and dry in an oven at 60° C. to obtain N-(4-ethylphenyl)thiosemicarbazide shown in formula I. Concrete reaction formula is as follows:

[0029]

[0030] 2. Dissolve 0.1950 g (1 mmol) of N-(4-ethylphenyl) thiosemicarbazide in 35 mL of aqueous ethanol solution with a volume concentration of 95%, then add 0.11 mL (1 mmol) of benz...

Embodiment 2

[0038] In this example, the benzaldehyde in Step 2 of Example 1 was replaced with equimolar p-bromobenzaldehyde, and the other steps were the same as in Example 1 to obtain white powder compound 2, which was named (E)-2-(4 -Bromobenzylidene)-N-(4-ethylphenyl)thiosemicarbazone, yield 86.7%, melting point: 194.6~195.1°C, structural characterization data are as follows:

[0039] Elemental analysis: The theoretical value is C% 53.04, H% 4.45, N% 11.60, the measured value is C% 53.21, H% 4.37, N% 11.57.

[0040] Infrared spectrum (KBr, cm -1 ): 3535 (N-H), 758 (C=S), 1617 (C=N).

Embodiment 3

[0042]In this example, the benzaldehyde in Step 2 of Example 1 was replaced with equimolar p-methoxybenzaldehyde, and the other steps were the same as in Example 1 to obtain a white powder compound 3, which was named (E)-2- (4-Methoxybenzylidene)-N-(4-ethylphenyl)thiosemicarbazone, yield 86.7%, melting point: 194.8-195.3°C, structural characterization data are as follows:

[0043] Elemental analysis: The theoretical value is C% 65.15, H% 6.11, N% 13.41, and the measured value is C% 65.27, H% 6.42, N% 13.29.

[0044] Infrared spectrum (KBr, cm -1 ): 3307 (N-H), 1206 (C=S), 1625 (C=N).

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Abstract

The invention discloses an N-substituent benzaldehyde thiosemicarbazone derivative and a preparation method and application thereof. The structural formula of the derivative is shown as follows: in the formula, R1 and R2 independently represent hydrogen atom, halogen, C1-C3 alkyl, C1-C3 alkoxy, trifluoromethyl, nitro, hydroxyl or cyano. The preparation method of the N-substituent benzaldehyde thiosemicarbazone derivative is simple, the reaction conditions are mild, the yield is high, and the industrial production is easy. The N-substituent benzaldehyde thiosemicarbazone derivative has simple structure and good biological activity, has good prevention and control effect on plant pathogenic fungi, has strong inhibitory activity, and has great value significance in preparing anti-plant pathogenic fungi.

Description

technical field [0001] The invention belongs to the technical field of novel green medicine synthesis, and specifically relates to N-substituent benzaldehyde thiosemicarbazone derivatives and a preparation method and application thereof. Background technique [0002] Pesticides have a long history. Since humans began to use pesticides, a large number of fungicides, insecticides, and herbicides have emerged, which have become a major research direction for many scholars and have contributed a lot to agricultural production. But following it, there are also problems such as the abuse of pesticides leading to serious environmental pollution, and the single variety of bacteria causing drug resistance. Therefore, it is imminent to develop green pesticides with high efficiency, low toxicity, low residue and novel mechanism of action. [0003] The existence of the central thiourea group (-HN-CS-NH-) in the thiourea derivatives is the key to the good biological activity of these co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C337/08A01N47/34A01P3/00
CPCA01N47/34C07C337/08
Inventor 黄洁张星齐帆王思凡
Owner NORTHWEST UNIV