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2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot

A technology of wheat take-all and benzoyl arylamine, which is applied in the field of compounds for preventing and controlling crop diseases and insect pests, can solve the problems that there are few varieties of fungicides for various root diseases of wheat, and achieve easy popularization and application, short synthesis steps, and easy raw materials The effect

Pending Publication Date: 2022-03-29
HENAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, in the prior art, there are still few fungicide varieties that can efficiently prevent and treat multiple root diseases of wheat, especially wheat take-all and wheat stem rot.

Method used

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  • 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot
  • 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot
  • 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of isopropyl 4-[(2-imidazol-1-yl)-6-fluorobenzamido]benzoate

[0030]

[0031] Step 1: Put 5.7 mmol of 2,6-difluorobenzoic acid into a three-necked reaction flask filled with 50 mL of dichloromethane and equipped with a reflux and gas absorption device, and slowly add 22.7 mmol of chlorinated chlorinated under normal temperature conditions Sulfone (SOCl 2 ) and 1ml DMF, heated to 40 o C continued to heat the reaction for 4 h. TLC detects that the reaction is complete, remove the solvent and excess thionyl chloride under negative pressure, then add 50 mL of fresh toluene to the reaction flask, and weigh 6.1 mmol 4-aminobenzoic acid isopropyl ester in batches to add to the reaction bottle, at 100 o Reaction 4 h under the temperature of ℃; TLC detects that after the reaction finishes, the reaction solution obtains the crude product of 4-(2,6-difluorobenzamido) isopropyl benzoate through neutralization, water washing and precipitation, and then passes throug...

Embodiment 2

[0034] Synthesis of isopropyl 4-[(2-imidazol-1-yl)-6-chlorobenzamido]benzoate

[0035]

[0036] Step 1: Put 5 mmol of 2-fluoro-6-chlorobenzoic acid into a three-necked reaction flask filled with 50 mL of dichloromethane and equipped with a reflux and gas absorption device, and slowly add 6 mmol of oxalyl chloride at room temperature (COCl) 2 and a few drops of DMF and incubated for 4 h. TLC detection until the reaction is complete, remove the solvent and excess oxalyl chloride under negative pressure, then add 50 mL of fresh toluene to the reaction flask, and weigh 10 mmol 4-aminobenzoic acid isopropyl ester in batches , at 100 o Reaction 4 h under ℃ temperature; After TLC detects that reaction finishes, reaction solution obtains the crude product of 4-(2-fluoro-6-chlorobenzamido) isopropyl benzoate through neutralization, water washing, stripping, then passes column Chromatographic separation gives a white solid;

[0037] Step 2: Mix 2 mmol 4-(2-fluoro-6-chlorobenzamid...

Embodiment 3

[0039] Synthesis of isopropyl 4-[(2-imidazol-1-yl)-6-bromobenzamido]benzoate

[0040]

[0041] Step 1: Put 5 mmol of 2-fluoro-6-bromobenzoic acid into a three-necked reaction flask filled with 50 mL of dichloromethane and equipped with a reflux and gas absorption device, and slowly add 6 mmol of chlorinated Sulfoxide SOCl 2 and a few drops of DMF, and incubated for 6 h. TLC detects that until the reaction is complete, remove the solvent and excess thionyl chloride under negative pressure, then add 50 mL of fresh toluene to the reaction flask, and weigh 7.5 mmol of isopropyl 4-aminobenzoate to add to the reaction in batches. bottle, at 100 o Reaction at temperature of C for 6 h; after TLC detection of the reaction, the reaction solution was neutralized, washed with water, and stripped to obtain the crude product of 4-(2-fluoro-6-bromobenzamido) isopropyl benzoate, and then passed through the column Chromatography afforded a white solid.

[0042] Step 2: Mix 2 mmol 4-(2-f...

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Abstract

The invention discloses a 2-imidazole benzoyl arylamine active compound for preventing and treating wheat take-all and wheat stem rot, which is characterized in that the 2-imidazole benzoyl arylamine active compound has a structure as shown in formula I: R1 and R2 are-H,-F,-Cl,-Br,-I,-CN,-CF3,-CHO,-C1-C4 alkyl or-C1-C4 halogenated alkyl or-O-R3, and R1 and R2 are not H at the same time; r < 3 > is alkyl of-C < 1 > to C < 4 > or halogenated alkyl or aryl of-C < 1 > to C < 4 >; the compound I has excellent inhibitory activity on wheat take-all bacteria and fusarium graminearum and fusarium pseudograminearum which can cause wheat stem rot, and can be applied to prevention and treatment of wheat take-all and wheat stem rot at the same time. The compound I is few in synthetic reaction steps, simple, smooth and safe in process, easy to purify and suitable for large-scale synthesis and development.

Description

technical field [0001] The invention relates to the field of compounds for preventing and controlling crop diseases and insect pests, in particular to a 2-imidazole benzoyl arylamide active compound used for the prevention and treatment of wheat take-all and wheat stem rot and a preparation method thereof. Background technique [0002] The development of agricultural modernization has brought about great changes in the agricultural farming mode, and returning straw to the field has become the main mode of operation in agriculture. However, because crop straw itself has the characteristics of breeding and carrying pathogenic bacteria, the return of straw to the field increases the risk and incidence of crop diseases to a certain extent. [0003] Therefore, in recent years, the occurrence and damage of wheat take-all and wheat stem rot have been increasing year by year, and have become a major threat to high-quality and high-yield wheat. The development and application of new...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/56A01N43/50A01P3/00
CPCC07D233/56A01N43/50
Inventor 程绎南李洪连孟颢光孙连省蒋振华闫景铭
Owner HENAN AGRICULTURAL UNIVERSITY
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