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Amide compound containing 3-trifluoromethylpyridine, preparation method and applications thereof, and a bactericide

A technology for trifluoromethyl pyridine amide and compound, which is applied in the field of trifluoromethyl pyridine amide-containing compounds and their preparation, can solve the problems of undisclosed trifluoromethyl pyridine amide-containing compounds and the like, and achieves simple post-processing , the raw materials are cheap and easy to obtain, and the reaction conditions are mild.

Active Publication Date: 2020-02-11
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Disclosed in CN1226244A is the purposes of N-carboxanilide as herbicide and insecticide, and specifically discloses the use of N-carboxanilide in the clubroot, oosporium, chytrid, zygomycetes, ascomycetes, basidiomycetes and deuteromycetes However, there is no specific disclosure that the compounds containing trifluoromethylpyridinamide have obvious inhibitory activity on succinate dehydrogenase and are effective against soybean rust, corn rust, wheat powdery mildew, melon powdery mildew, rice sheath blight, wheat Sheath blight, strawberry botrytis, peanut blight, cotton blight, wheat head blight, wheat take-all and cucumber target spot all have certain inhibitory activities

Method used

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  • Amide compound containing 3-trifluoromethylpyridine, preparation method and applications thereof, and a bactericide
  • Amide compound containing 3-trifluoromethylpyridine, preparation method and applications thereof, and a bactericide
  • Amide compound containing 3-trifluoromethylpyridine, preparation method and applications thereof, and a bactericide

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0063] Preparation Example 1: For the preparation of the compound shown in the intermediate formula (2-2)

[0064] Add 3mmol of the compound represented by formula (2-3), 3.6mmol of 2-aminophenol and 4.5mmol of potassium carbonate to a 50mL round bottom flask, then add 20mL of N,N-dimethylformamide, and heat up to 100 ℃, TLC monitors that the reaction of raw materials is stopped after the completion of the reaction, adding 50mL of ethyl acetate, washing with 50mL of saturated brine twice, adding anhydrous sodium sulfate to dry, removing the solvent under reduced pressure and column chromatography to obtain the intermediate (2-2). The compound shown, the structure of the compound shown in formula (2-2) is as shown in table 1.

[0065] Table 1

[0066] compound Substituent situation I1 R 11 for CF 3

Embodiment 1

[0067] Embodiment 1: for the compound shown in preparation formula (1)

[0068] Add 2-(7-azobenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate (15mmol), N,N-diiso Propylethylamine (15mmol) was dissolved in 50mL of dichloromethane, stirred evenly, then added 2-(trifluoromethyl)nicotinic acid (12mmol), and after stirring at room temperature for 2h, the formula (2- 2) The compound shown (10mmol) was added to the above solution, and TLC was used to monitor the reaction of the raw materials. After 4 hours of reaction at room temperature, the reaction was stopped. The system was washed twice with 50mL saturated brine, the organic phase was dried with sodium sulfate, and the solvent was removed under reduced pressure. Column chromatography The target compound was obtained as a yellow solid (the yield of the target product is the yield of one-step reaction).

[0069] Specifically, the structure and characterization data of the target compound are as follows:

[0070] Co...

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Abstract

The invention relates to the field of pesticide bactericides, and discloses an amide compound containing 3-trifluoromethylpyridine, a preparation method and applications thereof, and a bactericide, wherein the amide compound containing 3-trifluoromethylpyridine has a structure represented by a formula (1). According to the invention, by introducing the structure containing 3-trifluoromethylpyridine and the diphenyl ether fragment, the amide compound containing 3-trifluoromethylpyridine with wide activity is designed, and can be used as a completely-new succinate dehydrogenase inhibitor or bactericide.

Description

technical field [0001] The invention relates to the field of pesticide fungicides, in particular to a compound containing trifluoromethyl pyridine amides, a preparation method and application thereof, and a fungicide. Background technique [0002] Succinate dehydrogenase inhibitor fungicides have become the most promising class of fungicides in recent years because of their high efficiency, broad-spectrum fungicidal activity and environmental friendliness, and have attracted the attention of major pesticide companies in the world. [0003] The currently commercialized categories of fungicides that can be used as succinate dehydrogenase inhibitors mainly include: pyrazole amides, pyrazinamides, benzamides, tofuramide, oxathione amides, Thiazole amides, pyridine amides. In 2003, BASF launched the first broad-spectrum succinate dehydrogenase inhibitor - boscalid, which is active against almost all types of fungal diseases, and is effective in the control of powdery mildew, gra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/87A01N43/40A01P3/00
CPCC07D213/87A01N43/40
Inventor 杨光富李华
Owner HUAZHONG NORMAL UNIV
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