Preparation method and application of thiochroman-4-one derivative containing amide and oxime or oxime ether structure

A thiochroman and derivative technology is applied in the field of preparation and application of thiochroman-4-one derivatives containing amide and oxime or oxime ether structure, and can solve agricultural production loss, unfavorable ecological environment sustainable development, problems such as rapid onset

Active Publication Date: 2021-11-02
KAILI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Plant bacterial diseases have the characteristics of fast onset, great harm and wide distribution. So far, there are no effective control agents and control methods. Once the disease occurs, it will cause huge losses to agricultural production and seriously affect the increase of farmers' income and the development of the agricultural industry.
[0003] At present, the use of chemical agents to prevent and treat citrus canker is a method commonly used in production practice, but the long-term use of traditional chemical pesticides has also brought many problems: (1) The mode of action of most traditional chemical fungicides is non-specific Yes, while killing pathogenic bacteria, it also poisons beneficial microorganisms and insects, thereby endangering biodiversity and destroying ecological balance; (2) The long-term use of traditional chemical pesticides makes pathogenic bacteria gradually develop resistance, forcing people to continuously increase pesticides The amount of use will make the ecological problem more serious, which is not conducive to the sustainable development of the ecological environment

Method used

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  • Preparation method and application of thiochroman-4-one derivative containing amide and oxime or oxime ether structure
  • Preparation method and application of thiochroman-4-one derivative containing amide and oxime or oxime ether structure
  • Preparation method and application of thiochroman-4-one derivative containing amide and oxime or oxime ether structure

Examples

Experimental program
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Effect test

Embodiment 1

[0052] The present invention takes compound (Z)-6-chloro-2-(N-(4-fluorophenyl))formamide-4-methyloxime ether group thiochroman-4-one (compound 4e) as an example to illustrate the target The preparation of the compound, other different substituents take this as an example for reference synthesis;

[0053] The preparation method of (Z)-6-chloro-2-(N-(4-fluorophenyl)) formamide-4-methyl oxime ether group thiochroman-4-one (compound 4e), comprises the following steps:

[0054] (1) Synthesis of 6-chloro-2-carboxythiochroman-4-one

[0055] Add 4-chlorothiophenol, maleic anhydride, and toluene successively in a round-bottomed three-neck flask, and add 5 mL of toluene solution containing 2 drops of triethylamine dropwise in an oil bath at 50°C. After the addition is completed, The oil bath was reacted at 70°C for 4h. After the reaction was over, the toluene was removed under reduced pressure, and the residue was dissolved in 60 mL of dichloromethane. Under ice-bath conditions, 156 ...

Embodiment 2

[0061] The preparation method of (Z)-6-chloro-2-(N-phenyl)formamide-4-oximinothiochroman-4-one (compound 4a), comprises the following steps:

[0062] Referring to the steps of Example 1, the corresponding reactants and reaction parameters were modified to obtain compound 4a.

Embodiment 3

[0064] The preparation method of (Z)-6-chloro-2-(N-phenyl)formamide-4-methyl oxime ether group thiochroman-4-one (compound 4b), comprises the following steps:

[0065] Referring to the steps of Example 1, the corresponding reactants and reaction parameters were modified to obtain compound 4b.

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Abstract

The invention discloses a preparation method and application of a thiochroman-4-ketone derivative containing an amide and oxime or oxime ether structure. The compound can be used for effectively preventing and treating crop bacterial diseases such as rice bacterial leaf blight, rice bacterial streak, citrus canker and the like, wherein the EC50 values of the compound (Z)-6-chloro-2-(N-(4-fluorophenyl))formamide-4-methyl oxime ether thiochroman-4-one on pathogenic bacteria of rice bacterial blight, rice bacterial leaf streak and citrus canker are respectively 15 mu g / mL, 19 mu g / mL and 23 mu g / mL, so that the control effect is the best. The thiochroman-4-one derivative containing the amide and oxime or oxime ether structure is applied to prevention and treatment of bacterial diseases of crops, and is simple in structure, simple in preparation process, low in production cost and wide in application prospect. The general formula is shown in the specification.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to thiochroman-4-one derivatives containing amide and oxime or oxime ether structure, and also to the thiochroman-4-one containing amide and oxime or oxime ether structure The preparation method of the derivative, and the application of the thiochroman-4-one derivative containing amide and oxime or oxime ether structure in the preparation of medicines for preventing and treating bacterial and fungal diseases of plants. Background technique [0002] As a large agricultural country in my country, pesticides play a pivotal role in ensuring agricultural production. Plant bacterial disease is a third type of plant disease caused by bacteria infecting plants, second only to fungal diseases and viral diseases, such as citrus canker, rice bacterial blight, rice bacterial streak and tobacco Bacterial diseases such as bacterial wilt are important diseases worldwide. Plant bacteria...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/06A01N43/18A01P1/00
CPCC07D335/06A01N43/18Y02A50/30
Inventor 李培王翔
Owner KAILI UNIV
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