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2-(1,2,4-triazolyl)benzoyl arylamine active compound for inhibiting pathogens causing take-all disease of wheat

A technology for wheat take-all disease and benzoyl arylamide, which is applied in the field of compounds for preventing and controlling crop diseases and insect pests, can solve the problems of limited control effect of wheat take-all disease and few varieties, and achieves excellent inhibitory effect, smooth synthesis process, and guaranteed production safety. Effect

Active Publication Date: 2020-05-22
HENAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for the control of wheat take-all disease due to the limited control effect, there are few varieties available for selection.

Method used

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  • 2-(1,2,4-triazolyl)benzoyl arylamine active compound for inhibiting pathogens causing take-all disease of wheat
  • 2-(1,2,4-triazolyl)benzoyl arylamine active compound for inhibiting pathogens causing take-all disease of wheat
  • 2-(1,2,4-triazolyl)benzoyl arylamine active compound for inhibiting pathogens causing take-all disease of wheat

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 2-Chloro-N-(4-chlorophenyl)-6-(1H-1, 2, 4-triazol-1-yl)benzamide

[0046] 2-chloro-N-(4-chlorophenyl)-6-(1H-1,2,4-triazol-1-yl)benzamide

[0047]

[0048]Step 1 Mix 0.17 g (1 mmol) 2, 6-dichlorobenzonitrile, 0.09 g (1.3 mmol) technical grade 1, 2, 4-triazole, 0.43 g (1.3 mmol) anhydrous cesium carbonate and 9.5 mg (0.05 mmol) CuI and 8.1 mg (0.05 mmol) 8-hydroxyquinoline-N-oxide ligand were added to a 20 mL small reaction vial, and then 3 mL of N, N-dimethylformamide was measured, Add it to the reaction flask, place it in an oil bath at 85 °C, stir and heat for 12 h. After the reaction was complete as detected by TLC, potassium carbonate and unreacted triazole were filtered under reduced pressure, the filtrate was washed with water, extracted, concentrated, and separated by thin-layer chromatography to obtain 133 mg of off-white solid. 2-Chloro-6-(1H-1, 2, 4-triazol-1-yl)benzonitrile, off-white solid, melting point: 170℃-172 ℃ Yield: 65%. 1 H NMR (400 MHz, CDCl 3...

Embodiment 2～23

[0053] Synthesized according to the same method as in Example 1. The intermediate 2-chloro-6-(1H-1,2,4-triazol-1-yl)benzoic acid synthesized in Example 1 was used as a raw material, reacted with different substituted anilines, synthesized and separated. Compound structure, some physical and chemical parameters and characterization data such as figure 1 shown.

Embodiment 24～25

[0055] Using 2-chlorobenzonitrile and 2,3-dichlorobenzonitrile as raw materials respectively, the corresponding 2-(1H-1,2,4-triazol-1-yl) was synthesized according to the same method as in step 1 of Example 1 Benzonitrile and 3-chloro-2-(1H-1,2,4-triazol-1-yl)benzonitrile; ) benzonitrile and 3-chloro-2-(1H-1,2,4-triazol-1-yl) benzonitrile are intermediates, according to the same method as in Example 1 step 2,3, the substituted cyanide is hydrolyzed Obtain 2-(1H-1,2,4-triazol-1-yl) benzoic acid and 3-chloro-2-(1H-1,2,4-triazol-1-yl) benzoic acid respectively; In the same manner as in step 4 of Example 1, the obtained acid was condensed with isopropyl 4-aminobenzoate to obtain the target compound. Compound structure, some physical and chemical parameters and characterization data such as figure 2 shown.

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Abstract

The invention discloses a 2-(1,2,4-triazolyl)benzoyl arylamine active compound for inhibiting pathogens causing the take-all disease of wheat. The active compound is characterized in that the active compound has a structure shown as a formula I which is described in the specification. In the formula I, R1, R2, R3 and R4 are selected from the group consisting of -H, -F, -Cl, -Br, -I, -CN, -NO2, -CF3, -CHO, C1-C4 alkyl groups, C1-C4 haloalkyl groups and -O-R5; X and Y are selected from the group consisting of -H, -F, -Cl, -Br, -I, -CN, -NO2, -CF3 and -COOR6; R5 is selected from the group consisting of C1-C4 alkyl groups and C1-C4 haloalkyl groups or aryl groups; and R6 is selected from the group consisting of C1-C4 alkyl groups and C1-C4 haloalkyl groups or aryl groups. The compound I has anexcellent inhibition effect on the pathogens causing the take-all disease of wheat and can be applied to prevention and treatment of the take-all disease of wheat; the synthesis reaction process of the compound I is simple, smooth and safe; the produced compound I is easy to purify; and the synthesis reaction process is 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 novel 2-(1,2,4-triazole)benzoylarylamine compound for sterilization and a preparation method thereof, and a composition containing these compounds For the control of wheat take-all disease. Background technique [0002] With the development of society, especially the continuous progress of science and technology, the development of social productivity has been greatly promoted; With more modernization, agricultural farming patterns are also undergoing tremendous changes. [0003] Straw returning to the field has become the main mode of operation in agriculture. Since plant straw itself has the characteristics of breeding and carrying pathogenic bacteria, returning straw to the field will increase the risk and severity of crop diseases to some extent. Therefore, the prevention and control of crop diseases and the developme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08A01N43/653A01P3/00
CPCC07D249/08A01N43/653A01P3/00
Inventor 程绎南李洪连郭线茹蒋振华苏子洋张蒙萌孙连省申国富马艺超
Owner HENAN AGRICULTURAL UNIVERSITY
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