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2-thiazolyl acrylonitrile compounds and synthesis and application thereof

A technology of thiazolyl acrylonitrile and compound is applied in the field of 2-thiazolyl acrylonitrile compounds and their synthesis, and can solve the problem that 2-thiazolyl acrylonitrile compounds are not widely used and the like

Inactive Publication Date: 2010-06-09
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Thiazole compounds play a very important role in pesticides, but 2-thiazolyl acrylonitrile compounds are rarely used in pesticides

Method used

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  • 2-thiazolyl acrylonitrile compounds and synthesis and application thereof
  • 2-thiazolyl acrylonitrile compounds and synthesis and application thereof
  • 2-thiazolyl acrylonitrile compounds and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 4.72g (20mmol) 2-cyanomethyl-4-(2,6-difluorophenyl) thiazole and 3.05g (30mmol) triethylamine to 20mL tetrahydrofuran, add dropwise 2.76g (24mmol) chloroacetyl chloride , 40min dripping, then reacted at 66°C for 12h, after the reaction was completed, filtered, and the filter cake was recrystallized with chloroform to obtain light green crystal 2-[4-(2,6-difluorophenyl)-2-thiazolyl]- 4.40g of 3-hydroxy-3-chloromethylacrylonitrile, melting point 193-195°C, yield 70%.

[0027] of the compound 1 HNMR and IR are as follows,

[0028] 1 HNMR (CDCl 3 )δ=4.43(H, s, CH 2 Cl), 7.09~7.13 (2H, m, Ar- CH -CH- CH ), 7.40 (H, s, Triazole), 7.42~7.50 (H, m, Ar-CH- CH -CH), 14.67 (H, OH) IR (KBr, cm -1 )3378, 3155, 2201, 1524, 1610~1450, 1233, 783, 727

Embodiment 2

[0030] 4.72g (20mmol) 2-cyanomethyl-4-(2,6-difluorophenyl) thiazole and 1.13g (28mmol) sodium hydroxide were added to 25mL 1,4-dioxane, and 2.10g ( 26mmol) of acetyl chloride, dripping for 40min, then reacted at 100°C for 6h, after the reaction was completed, filtered, and the filter cake was recrystallized with chloroform to obtain white flaky crystals 2-[4-(2,6-difluorophenyl)-2 -Thiazolyl]-3-hydroxy-3-methacrylonitrile 4.36g, melting point 197-198°C, yield 78%.

[0031] of the compound 1 HNMR and IR are as follows,

[0032] 1 HNMR (CDCl 3 )δ=2.41(3H, s, CH 3 ), 7.05~7.09 (2H, m, Ar- CH -CH- CH ), 7.36~7.46 (2H, m, Ar-CH- CH -CH& Triazole)

[0033] IR (KBr, cm -1 )3453, 3179, 2191, 1513, 1610~1450, 1378, 1246, 790, 712

Embodiment 3

[0035] Add 4.72g (20mmol) 2-cyanomethyl-4-(2,6-difluorophenyl) thiazole and 3.22g (30mmol) sodium carbonate to 20mL dichloromethane, add dropwise 2.27g (24mmol) propionyl chloride , 40min dripping, and then reacted at 40°C for 12h, after the reaction was completed, filtered, and the filter cake was recrystallized with chloroform to obtain a light green solid 2-[4-(2,6-difluorophenyl)-2-thiazolyl]- 4.21 g of 3-hydroxy-3-ethylacrylonitrile, melting point 172-174°C, yield 72%.

[0036] of the compound 1 HNMR and IR are as follows,

[0037] 1 HNMR (CDCl 3 ) δ = 1.25 ~ 1.28 (3H, t, CH 3 ), 2.70~2.75 (2H, m, CH 2 ), 7.05~7.09 (2H, t, Ar- CH -CH- CH ), 7.37~7.41 (2H, m, Ar-CH- CH -CH& Triazole), 14.67 (H, OH)

[0038] IR (KBr, cm -1 )3450, 3161, 2194, 1513, 1620~1480, 1459, 1237, 997

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Abstract

The invention discloses 2-thiazolyl acrylonitrile compounds and a synthesis method and application thereof. The structure of the 2-thiazolyl acrylonitrile compounds is shown in a formula (I), wherein R is phenyl. The synthesis method for the 2-thiazolyl acrylonitrile compounds comprises the following steps: performing nucleophilic substitution reaction on 2-cyanomethyl-4-(2', 6'-difluoropheny) thiazole shown in a formula (II) and acyl chloride shown in a formula (III) in the presence of an acid binding agent in a protic organic solvent or non-protonic organic solvent at the temperature of between 0 and 100 DEG C for 1 to 20 hours to obtain reaction liquid; and processing the reaction liquid to obtain the 2-thiazolyl acrylonitrile compounds. The 2-thiazolyl acrylonitrile compounds can be used as weedicides and bactericides, and new substances are added for screening the weedicides and bactericides.

Description

technical field [0001] The invention relates to a 2-thiazolyl acrylonitrile compound and its synthesis method and application. Background technique [0002] Thiazole compounds play a very important role in pesticides, but 2-thiazolylacrylonitrile compounds are rarely used in pesticides. Due to the high efficiency, low toxicity and structural diversity shown by 2-thiazolyl acrylonitrile compounds, they have very broad research and development prospects. In the present invention, a series of 2-thiazolyl acrylonitrile compounds are obtained by substituting the 3-position hydrogen with alkane and an aromatic ring. Contents of the invention [0003] The technical problem to be solved by the present invention is to provide a biologically active 2-thiazolylacrylonitrile compound, its synthesis method and its application. [0004] The structure of the 2-thiazolyl acrylonitrile compound of the present invention is shown in formula (I) [0005] [0006] where R is C 1 ~C 10 ...

Claims

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Application Information

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IPC IPC(8): C07D277/30A01N43/78A01P13/00A01P3/00
Inventor 沈德隆杨鹏谭成侠翁建全曹耀艳刘会君
Owner ZHEJIANG UNIV OF TECH
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