3-pyridyl-3-amino-2-cyanoacrylate compound, and preparation method and application thereof

A technology of cyanoacrylate and compound, which is applied in the field of 3-pyridyl-3-amino-2-cyanoacrylate compound and its preparation, can solve the problem of narrow action spectrum of cyanostrobin and the use of dosage is not very high. Efficiency and other issues, to achieve the effect of outstanding prevention and control effect

Active Publication Date: 2019-06-11
JIANGSU PESTICIDE RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no second fungicide with this type of action mechanism has been found. During use, it was found that cyclostrobin has a narrow action spectrum, and the dosage has not reached a very efficient level.

Method used

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  • 3-pyridyl-3-amino-2-cyanoacrylate compound, and preparation method and application thereof
  • 3-pyridyl-3-amino-2-cyanoacrylate compound, and preparation method and application thereof
  • 3-pyridyl-3-amino-2-cyanoacrylate compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0058] The synthetic route of general formula (1) compound is:

[0059]

[0060]

[0061] Compound NO.001 (R=pyridin-4-yl, R 1 = ethyl, R 2 =ethyl): Synthesis of ethyl 2-cyano-3-amino-3-(pyridin-4-yl)acrylate

[0062] Add 5.0g (48mmol) of 4-cyanopyridine and 2.2g (48mmol) of absolute ethanol into 20ml of dichloromethane, cool down to 0°C, and pass in 5.26g (144mmol) of hydrochloric acid gas until the reaction solution is clarified, and keep it warm for the reaction until the raw materials are consumed. Add 10% sodium carbonate aqueous solution dropwise under stirring until pH = 7-8, let stand to separate the oil layer, and remove the solvent to obtain 7.7 g of ethyl pyridine-4-carboximidate, content: 92.0%, yield: 98.4% .

[0063] Add 8.0g (53mmol) of ethyl pyridine-4-carboximidate and 0.3g (3mmol) of triethylamine into 40ml of absolute ethanol, heat to reflux at about 78°C, and dropwise add 6.0g (53mmol) of ethyl cyanoacetate Esters, after dropping the heat preserv...

preparation Embodiment 1

[0076] Formulation Example 1: emulsion in water

[0077] 20 parts of the compound of the present invention, 12 parts of toluene, 6 parts of ethylene oxide-propylene oxide block copolymer, 6 parts of xanthan gum, 4.5 parts of ethylene glycol antifreeze, 4 parts of propylene glycol antifreeze, and 0.8 parts of organic silicon , 46.7 parts of water, obtain the water emulsion that active ingredient is 20% by water emulsion processing technology.

preparation Embodiment 2

[0078] Formulation Example 2: Suspending agent:

[0079]25 parts of the compound of the present invention, 6 parts of wetting agent sodium p-methyl fatty amidobenzene sulfonate, 2 parts of dispersant alkylphenol polyoxyethylene ether formaldehyde condensate, 6 parts of thickener carboxymethylcellulose sodium, 1 part of preservative sodium salicylate, 2 parts of antifreeze agent propylene glycol, 1 part of antifoaming agent silicone oil, 57 parts of water, according to the suspending agent processing technology to obtain a suspending agent with an active ingredient of 25%.

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PUM

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Abstract

The invention discloses a 3-pyridyl-3-amino-2-cyanoacrylate compound, and a preparation method and application thereof. The structure of the compound is shown in a general formula (1). The preparationmethod of the compound comprises the following steps: taking a compound shown in a formula (II) as a raw material to carry out a reaction with a fatty alcohol in an organic solvent in the presence ofhydrogen chloride to obtain pyridyl imidate, and carrying out a reaction on the pyridyl imidate with cyanoacetate in an organic solvent under catalysis of a catalyst for condensation to prepare the 3-pyridyl-3-amino-2-cyanoacrylate compound. The compound has bactericidal activity and can be used for preventing and treating diseases.

Description

technical field [0001] The invention relates to a pesticide fungicide, in particular to a 3-pyridyl-3-amino-2-cyanoacrylate compound and a preparation method and application thereof. Background technique [0002] Bioactive acrylic acid derivatives are currently one of the goals of new pesticide development and research, and have considerable scalability and structural modification potential. Among them, 2-cyano-3-aminoacrylate derivatives are used as pesticide fungicides. , achieved good results in recent years. [0003] ZL01115593.0 reports 2-cyano-3-substituted phenyl acrylate compounds, compositions and their preparation methods, and their application in crop fungicides, among which the successfully developed fungicide cyclostrobin is effective against Fusarium Pesticide diseases have excellent control effects, and can greatly reduce the disease toxins that are harmful to the human body due to these diseases. The team of Professor Zhou Mingguo from Nanjing Agricultural ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/57A01N43/40A01P3/00
Inventor 曹庆亮马海军张洪全蔡义强刁亚梅
Owner JIANGSU PESTICIDE RES INST
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