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Novel substituted phenylpropionaldehyde (benzylideneacetaldehyde) thiosemicarbazone compounds and applications of the compounds as agricultural bactericides

A compound, multi-substituted technology, used in fungicides, applications, biocides, etc.

Inactive Publication Date: 2014-04-02
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Previous work in this laboratory has synthesized a series of substituted phenylfuran formaldehyde thiosemicarbazone compounds and substituted phenylpropionaldehyde thiosemicarbazone compounds, and found that they have inhibitory effect on cotton bollworm tyrosinase (CN201010100979.1, CN201110099255 .4), but has not been reported as an antifungal agent

Method used

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  • Novel substituted phenylpropionaldehyde (benzylideneacetaldehyde) thiosemicarbazone compounds and applications of the compounds as agricultural bactericides
  • Novel substituted phenylpropionaldehyde (benzylideneacetaldehyde) thiosemicarbazone compounds and applications of the compounds as agricultural bactericides
  • Novel substituted phenylpropionaldehyde (benzylideneacetaldehyde) thiosemicarbazone compounds and applications of the compounds as agricultural bactericides

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Experimental program
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Effect test

Embodiment 1

[0013] Embodiment 1: the preparation of 4-bromophenylacrylaldehyde thiosemicarbazone (I-5)

[0014] Add 1.06g (5mmol) 4-bromophenylacrolein, 25mL organic solvent ethanol and 0.41g (4.5mmol) thiosemicarbazide to a 50mL three-neck flask, add 3.0mg (0.05mmol) acidic compound acetic acid in one batch, and heat to 78°C The condensation reaction was carried out under reflux for 1 hour, and the reaction was stopped. The reaction solution was spin-dried and recrystallized from ethanol to obtain 0.98 g of a yellow solid, yield: 77%. The appearance and fusing point of this yellow solid product are shown in Table 1, and its 1 H NMR spectrum data are shown in Table 2. As can be seen from Table 2, the structure of the product is correct.

[0015] According to the same method as above for the preparation of compound I-5, only the compound shown in formula I is replaced according to the R group shown in Table 1 to obtain the corresponding products I-1, I-2, I-3 and I-4 , the appearance, ...

Embodiment 2

[0021] Embodiment 2: the inhibitory activity of formula I compound to 4 kinds of plant pathogenic bacteria

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Abstract

The invention provides novel substituted phenylpropionaldehyde (benzylideneacetaldehyde) thiosemicarbazone compounds shown as the formula I and applications of the compounds as agricultural bactericides, wherein R is C1-C4 alkyl, C1-C4 alkoxy, halogen, trifluoromethyl, trifluoromethoxy and nitro; the substitution position of the R is mono-substituted, di-substituted or multi-substituted; the R refers in particular to 2-fluro, 4-bromo, 3-trifluoromethyl, 3-methyl and 3,4,5-trimethoxy, and -A- is -CH2-CH2- or -CH=CH-. Bactericidal activity tests show that the compounds shown in the formula I have good inhibition functions for four plant pathogens (botrytis cinerea, sclerotinia rot of colza, fusarium wilt of cotton and rice sheath blight disease), and can be used for controlling the plant pathogens as bactericides.

Description

technical field [0001] The invention relates to a class of novel substituted phenylacrylic (enyl) aldehyde thiosemicarbazone compounds and the application of the compounds as agricultural fungicides. Background technique [0002] There are more than 1 million species of fungi on the earth, which have a great impact on human life. Fungicides have been widely used since the early 20th century. However, with the continuous expansion of the scope of application and the rapid reproduction and mutation of fungi, the existing fungicides inevitably have problems such as phytotoxicity and drug resistance. Therefore, it is urgent to develop new high-efficiency, broad-spectrum, and environmentally safe fungicides. [0003] Thiosemicarbazone compounds have multiple biological activities, and their antibacterial, antifungal, antiviral, anti-tuberculosis, anti-tumor, anti-leprosy, anti-parasitic and other activities have been extensively studied. In 1946, Domagk et al. (Naturwissenscha...

Claims

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Application Information

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IPC IPC(8): C07C337/08A01N47/34A01P3/00
Inventor 杨新玲徐焱凌云李慧苗宏健雷鹏
Owner CHINA AGRI UNIV
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