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M-diamide compound and application thereof

A technology of meta-diamide and compound, applied in the field of meta-diamide compounds, can solve the problems of poor quick-acting, poor insecticidal effect, restricted promotion and application, etc.

Pending Publication Date: 2021-08-31
CAC NANTONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the meta-diamide compounds such as KC1 and KC2 show certain insecticidal activity, their insecticidal effect at low doses is not good, and their quick-acting properties are not good, which limits their further promotion in the field of pesticides. and application

Method used

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  • M-diamide compound and application thereof
  • M-diamide compound and application thereof
  • M-diamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0158] This example provides a kind of intermediate diamide compound, that is, N-{3-[(2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)- Preparation of 6-trifluoromethylphenyl)carbamoyl]-2-fluorophenyl}-N-ethylbenzamide (compound 1), the structure is as follows:

[0159]

[0160] The preparation method comprises the following steps:

[0161] (1) Synthesis of 3-ethylamino-2-fluorobenzoic acid methyl ester

[0162]

[0163] Dissolve methyl 2-fluoro-3-aminobenzoate (5.00g, 29.56mmol) in N,N-dimethylformamide (50mL), add bromoethane (6.44g, 59.12mmol) and potassium carbonate in sequence (12.26g, 88.68mmol), reflux for 16h. Thin-layer chromatography (TLC) monitored that when the reaction no longer proceeded, the reaction was terminated. Cool the reaction solution to room temperature, add ethyl acetate (200mL), water (100mL), extract and separate the layers, take the organic layer, wash the organic layer with saturated brine, dry over anhydrous sodium sulfate, concentrate un...

Embodiment 2

[0180] This example provides an intermediate diamide compound, namely N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-trifluoro Preparation of methylphenyl]-3-[N-(ethyl)-2-chloro-isonicotinamide]-2-fluorobenzamide (compound 46) with the following structure:

[0181]

[0182] The preparation method comprises the following steps:

[0183] (1) N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-trifluoromethylphenyl]-3-(ethyl Synthesis of (amino)-2-fluorobenzamide

[0184]

[0185] 3-Amino-N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-trifluoromethylphenyl]-2- Fluorobenzamide (3.00g, 5.55mmol) was dissolved in methanol (50mL), acetaldehyde (610mg, 5.50mmol) and acetic acid (2.0g, 33.0mmol) were added successively, stirred for 4 hours under ice bath, and cyano Sodium borohydride (1.0 g, 16.5 mmol). When TLC monitors that the reaction no longer proceeds, the reaction is terminated. Add saturated aqueous sodium bicarbonate solution to the reaction solution, ad...

Embodiment 3

[0195] This example provides an intermediate diamide compound, namely N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-trifluoro Preparation of methylphenyl]-3-[N-(n-butyl)-benzamido]-2-fluorobenzamide (compound 82) with the following structure:

[0196]

[0197] The preparation method comprises the following steps:

[0198] (1) N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-trifluoromethylphenyl]-3-(n Synthesis of Butylamino)-2-Fluorobenzamide

[0199]

[0200] 3-Amino-N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-trifluoromethylphenyl]-2- Fluorobenzamide (1.82g, 3.30mmol) was dissolved in 1,2-dichloroethane (30mL), and n-butyraldehyde (264mg, 3.60mmol) and acetic acid (1.2g, 20.0mmol) were added successively, and stirred under ice bath After 2 hours, sodium triacetoxyborohydride (1.4 g, 6.60 mmol) was added in portions. When TLC monitors that the reaction no longer proceeds, the reaction is terminated. Add saturated aqueous sodium bicarbonate solutio...

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Abstract

The invention provides a m-diamide compound and application thereof. The m-diamide compound has a structure as shown in a formula I. Through screening and special design of molecular structures and functional groups, the m-diamide compound has a remarkable effect on prevention and control of diseases and insect pests and nematodes in agriculture and forestry and pests in the field of sanitation; and the m-diamide has excellent insecticidal effect at a low dosage, fast acts, has insecticidal activity after being applied for 1 day and very high insecticidal activity within 3 days, has good fast-acting property, can be applied at a low dosage, is more beneficial to environmental protection, and is simple and efficient in preparation method, easy for large-scale production and wide in application prospect.

Description

technical field [0001] The invention belongs to the technical field of insecticides, and in particular relates to a meta-diamide compound and its application. Background technique [0002] In the production of crops such as agriculture, forestry and horticulture, the yield reduction of crops and commercial crops caused by pests is still very significant. Due to the resistance of pests to existing insecticides and the environmental unfriendliness of existing pesticides, it is always necessary to develop new insecticides with better activity, lower dosage, and more environmental friendliness. [0003] Diamide insecticides have been hot products in the market since their inception, and their representative compounds include flubendiamide and chlorbendiamide. However, with the increasing pressure on environmental protection and the increasing problem of pest resistance, phthalamide insecticides such as flubendiamide and chlorbendiamide have been unable to meet the application r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/42C07C255/57C07D213/82C07D213/81A01N37/46A01N43/40A01P7/04
CPCC07C237/42C07C255/57C07D213/82C07D213/81A01N37/46A01N43/40
Inventor 刘吉永王锐之相君成陈晨周丽琪吕亮丁福栋庄彩霞倪珏萍
Owner CAC NANTONG CHEM
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