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3-amino-2-cyanoacrylate type compound and application thereof

A technology of cyanoacrylates and compounds, applied in the field of 3-amino-2-cyanoacrylate compounds, which can solve the problems of limited application range and low solubility

Inactive Publication Date: 2019-06-14
JIANGSU PESTICIDE RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is one of the few domestically invented pesticide varieties, but cyclostrobin, like other 3-amino-2 amino-acrylates, has its insurmountable problem, that is, the general solubility is very small, which limits its Application range

Method used

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  • 3-amino-2-cyanoacrylate type compound and application thereof
  • 3-amino-2-cyanoacrylate type compound and application thereof
  • 3-amino-2-cyanoacrylate type compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078]

[0079] In a four-neck flask equipped with a thermometer, mechanical stirring, reflux condenser, and dropping funnel, suspend 21.2 g (0.1 mol) of cyclostrobin (2-cyano-3-amino-3-phenylacrylate ethyl ester) In 600g of ethylene dichloride solution, 17.4g (0.2mol) morpholine joins in this solution, and system is warmed up to 70 ℃, and at this temperature, the formaldehyde (0.2mol) aqueous solution of 17.5g35% in 30 minutes is added dropwise to In the reaction solution, after the dropwise addition is completed, the reaction is continued at this temperature for 1 hour, the temperature is lowered to 0 degrees, the unreacted substances are filtered off, the phases are separated, and the dichloroethane phase is concentrated to obtain the Mannich base of cyclostrobin. Recrystallization obtained 10 g of morpholine Mannich base of cyclostrobin, ie compound NO.1.

Embodiment 2

[0081]

[0082] In a four-necked flask equipped with a thermometer, mechanical stirring, reflux condenser and dropping funnel, 2.12g (0.01mol) cyclostrobin (2-cyano-3-amino-3-phenylacrylate ethyl ester) Suspended in 60g of toluene solution, 1.42g (0.02mol) tetrahydropyrrole was added to the solution, the system was heated up to 110°C, at this temperature, 1.92g of furfural (0.2mol) was added dropwise to the reaction solution within 30 minutes After the dropwise addition, the reaction was continued at this temperature for 1 hour, the temperature was lowered to 0°C, the unreacted substances were filtered off, the phases were separated, and the toluene phase was concentrated and separated by column chromatography to obtain 0.5 g of compound NO.8.

Embodiment 3

[0084]

[0085] In a four-neck flask equipped with a thermometer, mechanical stirring, reflux condenser, and dropping funnel, suspend 2.12 g (0.01 mol) of cyclostrobin (2-cyano-3-amino-3-phenylacrylate ethyl ester) In 60g of toluene solution, 1.74g (0.02mol) of morpholine was added to the solution, and the system was heated to 110°C. At this temperature, 2.14g (0.2mol) of pyridine-4 formaldehyde was added dropwise to the reaction within 30 minutes. solution, after the dropwise addition was completed, the reaction was continued at this temperature for 4 hours, the temperature was lowered to 0°C, the unreacted substances were filtered off, the phases were separated, and the toluene phase was concentrated and then separated by column chromatography to obtain 0.6g of Mannystrobin of cyclostrobin. Xi base, compound NO.15.

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PUM

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Abstract

The invention discloses a 3-amino-2-cyanoacrylate type compound and application thereof. The compound has a general formula shown in a formula (I). According to the invention, a cyanoacrylate type mannich alkali type bactericide is prepared. The bactericide has an excellent prevention and control effect on fusaria; and due to the alkalinity of mannich alkali, the bactericide can be combined with common inorganic acid and organic acid to generate salt capable of being dissolved in water. The formula (I) is shown in the description.

Description

technical field [0001] The invention belongs to agricultural fungicides and the same, in particular to 3-amino-2-cyanoacrylate compounds and applications thereof. Background technique [0002] Compounds with enaminoester structure have special biological activity, and can usually be used as medicine, veterinary medicine, pesticide and antibacterial agent. Cyanoacrylate compounds, due to their special killing activity against Fusarium, unique mechanism of action, and the characteristics of reducing Fusarium toxin, [0003] Cyclostrobin, (Z) ethyl 2-cyano-3 amino-3 phenylacrylate (pesticide name Cyclostrobin) is a cyanoacrylate fungicide independently created by Jiangsu Pesticide Research Institute Co., Ltd. Apply for a patent (CN1317483A) in 2001. The compound is highly efficient, slightly toxic, broad-spectrum, low-residue, and environmentally friendly. It has protective and therapeutic effects on plant diseases caused by Fusarium, and can be applied to the prevention and ...

Claims

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Application Information

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IPC IPC(8): C07D295/13C07D405/06C07D213/38C07C255/42C07C253/30C07D307/52C07D417/06C07D413/06C07D277/04C07D263/04C07D233/02A01N43/84A01N43/60A01N43/36A01N43/76A01N43/50A01N43/78A01N37/44A01N55/10A01N47/12A01N41/10A01N41/08A01N41/06A01N43/08A01N43/28A01P3/00
Inventor 谭波王洪雷曹杨马海军刁亚梅蔡义强
Owner JIANGSU PESTICIDE RES INST
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