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Amide derivative containing alpha-aminoketone structure and preparation method and application thereof

The technology of amide derivatives and amino ketones is applied in the field of amide derivatives containing an α-amino ketone structure and the preparation thereof, which can solve the problems of outstanding pest resistance and other problems, and achieve the effects of simple and easy preparation process and easy availability of raw materials.

Active Publication Date: 2017-08-18
HUBEI BIOPESTICIDE ENG RES CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, with the excessive and frequent use of such insecticides, the problem of pest resistance will become increasingly prominent

Method used

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  • Amide derivative containing alpha-aminoketone structure and preparation method and application thereof
  • Amide derivative containing alpha-aminoketone structure and preparation method and application thereof
  • Amide derivative containing alpha-aminoketone structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The structural formula of some amide derivatives containing α-aminoketone structure of the present invention is one of the specific compounds listed in Table 1:

[0034] Table 1: Representative compounds shown in structural formula I

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

Embodiment 2

[0046] Numbering is the preparation of the compound of I1 among the embodiment 1, and its reaction formula is:

[0047]

[0048] Its preparation method comprises the following steps:

[0049] a) Using anthranilic acid (compound 1a) and 3-bromo-2-methylbenzoic acid (compound 2a) as starting materials, the heterocyclization reaction was carried out under the combined action of methanesulfonyl chloride and pyridine to obtain intermediate 2 -(3-bromo-2-methylphenyl)-4H-benzoxazin-4-one (compound 3a), the reaction temperature is 20°C, and the reaction solvent is 1,2-dichloroethane;

[0050]b) Using the intermediate 2-(3-bromo-2-methylphenyl)-4H-benzoxazin-4-one (compound 3a) as the starting material, it undergoes a substitution reaction with isopropanolamine 4a to obtain Ring-opening intermediate 5a, the reaction temperature is 30°C, and the reaction solvent is acetonitrile;

[0051] c) The intermediate 5a was oxidized under the action of oxidant m-chloroperoxybenzoic acid (MC...

Embodiment 3

[0053] Numbering is the preparation of the compound of I9 among the embodiment 1, and its reaction formula is:

[0054]

[0055] Its preparation method comprises the following steps:

[0056] a) Starting with 2-amino-5-chloro-3-methylbenzoic acid (compound 1b) and 2-chloro-4-thiamphenicol benzoic acid (compound 2b), in the common combination of methanesulfonyl chloride and pyridine The heterocyclization reaction under the influence of The reaction temperature is 25°C, and the reaction solvent is tetrahydrofuran;

[0057] b) starting from the intermediate 6-chloro-2-(2-chloro-4-thiamphenicolphenyl)-8-methyl-4H-benzoxazin-4-one (compound 3b), and Isopropanolamine 4a is subjected to substitution reaction to obtain ring-opening intermediate 5b, the reaction temperature is 30°C, and the reaction solvent is dichloromethane;

[0058] c) Dissolving the intermediate 5b in an appropriate amount of tetrahydrofuran, and performing an oxidation reaction using Sarrett reagent (PCC) to...

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Abstract

The invention discloses an amide derivative containing an alpha-aminoketone structure and a preparation method and application thereof. A structural formula of the amide derivative is shown in the attached figure. The preparation method comprises the following step of using substituted o-aminobenzoic acid and substituted carboxylic acid R3COOH as initial raw materials, and performing a series of reactions, so as to obtain the amide derivative. When the amide derivative is used for preparing an insecticide, the amide derivative containing the alpha-aminoketone structure is dissolved into a thinner, so as to obtain the insecticide; the weight percentage of the amide derivative containing the alpha-aminoketone structure in the insecticide is 0.001 to 99.99%. During specific application, the insecticide is a conventional preparation, such as a water emulsion, a suspension agent, wettable powder and a water dispersible granule.

Description

technical field [0001] The invention belongs to the technical field of organic medicine synthesis, and specifically relates to an amide derivative containing an α-aminoketone structure, a preparation method and application thereof. Background technique [0002] At present, agricultural modernization, environmental protection, resistance management, and intellectual property protection all require strengthening research on the creation and research of new pesticides from different aspects, and the development of highly efficient and environmentally friendly "green ecological pesticides"; The discovery of bisamide insecticides is another major breakthrough in the history of chemical pesticide development following the neonicotinoid insecticides represented by imidacloprid. It is a new type of green insecticide with low animal toxicity, safety, unique mechanism of action, no cross-resistance and environmental friendliness. At present, Flubendiamide (Nihon Nohyaku and Bayer), Z...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D231/14C07D233/90C07C237/42C07C317/44A01N43/56A01N43/50A01N37/46A01N41/10A01P7/04A01P7/02
CPCA01N37/46A01N41/10A01N43/50A01N43/56C07C237/42C07C317/44C07D231/14C07D233/90C07D401/04
Inventor 柯少勇张志刚石丽桥王开梅张亚妮龙同黄大野梁英江爱兵杨自文
Owner HUBEI BIOPESTICIDE ENG RES CENT
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