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Medicine composition containing m-diamide compound and application of medicine composition

A technology for metadiamide and compound, which is applied in the field of pharmaceutical compositions containing metadiamide compounds, can solve the problem of incomplete insecticidal activity and the like, achieve good effect, reduce damage to plants and humans, and reduce drug residues. Effect

Active Publication Date: 2020-02-21
CAC NANTONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the continuous use of pesticides, pests and diseases will develop resistance to some existing pesticide products, and the insecticidal activity of existing pesticide varieties does not always meet the needs of many agricultural practices

Method used

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  • Medicine composition containing m-diamide compound and application of medicine composition
  • Medicine composition containing m-diamide compound and application of medicine composition
  • Medicine composition containing m-diamide compound and application of medicine composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] N-[2-Bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-(trifluoromethyl)phenyl]-3-[N- (Cyclopropylmethyl)-benzamido]-2-fluorobenzamide (compound number 1):

[0085] (1) Synthesis of 2-fluoro-[3-(cyclopropylmethyl)amino]benzoic acid methyl ester

[0086]

[0087] Add methyl 2-fluoro-3-aminobenzoate (20g, 118.23mmol), bromomethylcyclopropane (20.75g, 153.70mmol), potassium carbonate (21.24g, 153.70mmol), N, N-dimethylformamide (200 mL) was stirred under reflux for 16 h. When TLC monitored that the reaction did not proceed, the heating was turned off to terminate the reaction. After the reaction solution was cooled to room temperature, water (200 mL) was added to the reaction solution, extracted with ethyl acetate (100 mL), the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was washed with Purified by column chromatography (eluent is petroleum ether: ethyl acetate = 10:1), the produ...

Embodiment 2

[0100] N-[2-Bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-trifluoromethoxyphenyl]-3-[N-( Synthesis of cyclopropylmethyl)benzamido]-2-fluorobenzamide (compound number 3)

[0101]

[0102] Add 2-fluoro-3-(N-(cyclopropylmethyl)benzamide)benzoic acid (0.50g, 1.60mmol), toluene (6mL), thionyl chloride (1.07g, 9.00mmol) to the reaction flask successively ), the reaction was stirred under reflux for 2 h, the toluene was concentrated under reduced pressure, and the concentrated residue was dissolved in tetrahydrofuran (3 mL) for use.

[0103] 2-Bromo-4-heptafluoroisopropyl-6-trifluoromethoxyaniline (0.68g, 1.60mmol) was dissolved in tetrahydrofuran (4mL), and 2M lithium diisopropylamide was added dropwise at -70°C Tetrahydrofuran solution (0.96mL, 1.93mmol) was added dropwise after 5min with the tetrahydrofuran solution to be used in the next step, stirred at -70°C for 30min, then raised to room temperature and continued to stir for 30min. Thin-layer chromatography (TLC) monitor...

Embodiment 3

[0106] N-[2-Bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-(trifluoromethyl)phenyl]-3-[N- Preparation of (cyclopropylmethyl)-4-cyanobenzamido]-2-fluorobenzamide (compound number 4):

[0107] (1) Synthesis of methyl 2-fluoro-3-[N-(cyclopropylmethyl)-4-cyanobenzamido]benzoate

[0108]

[0109] Add 4-cyanobenzoic acid (0.80g, 5.38mmol), toluene (6mL), and thionyl chloride (3.2g, 26.9mmol) to the reaction flask successively, stir the reaction under reflux for 2h, and concentrate the toluene under reduced pressure , the concentrated residue was dissolved in THF (3 mL) for use. Dissolve 2-fluoro-[3-(cyclopropylmethyl)amino]methyl benzoate (1.0g, 4.48mmol) in tetrahydrofuran (6mL), add triethylamine (0.74g, 5.38mmol), dropwise add 4 -The tetrahydrofuran solution of cyanobenzoyl chloride was stirred at room temperature for 4h. When TLC monitors that the reaction no longer proceeds, the reaction is terminated. Water (20 mL) was added to the reaction solution, extracted with ethy...

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PUM

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Abstract

The invention provides a medicine composition containing an m-diamide compound and application of the medicine composition. The medicine composition comprises an effective component A and an effectivecomponent B, wherein the effective component A is an m-diamide compound of a structure of a formula I shown in the description; and the effective component B comprises any one or a combination of twoof other insecticides. The composition with the effective component A and the effective component B, which is provided by the invention, has unique functions of synergism, resistant insect control, activity spectrum expansion, virus transmission insect control, and the like, and is capable of effectively preventing and treating a diversity of diseases and insects of crops such as rice, corn, wheat, vegetables, fruit trees, flowers, oil plants and sugar plants, and gardening and forestry as well.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical compositions for preventing and controlling harmful organisms, and relates to a pharmaceutical composition containing diacids and applications thereof. Background technique [0002] In the production of crops such as agriculture and horticulture, the damage caused by diseases and insect pests is still very significant. Due to the resistance of pests to existing pesticides and the unfriendly environment of existing pesticides, it is always necessary to develop products with better activity and lower dosage. , A new insecticide or insecticide composition that is more environmentally friendly. [0003] For example, CN101208009A discloses that a composition containing a meta-diamide compound has an insecticidal effect, and various insecticides and fungicides of different structural types are widely used in various crops in the prior art. With the continuous use of pesticides, pests and disease...

Claims

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Application Information

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IPC IPC(8): A01N37/22A01N47/34A01N41/02A01N47/24A01N47/22A01N57/12A01N57/16A01N57/14A01N53/08A01P7/04A01P3/00A01P1/00A01P7/02
CPCA01N57/16A01N37/46A01N41/10A01N43/82A01N51/00A01N43/90A01N57/28A01N43/76A01N43/56A01N43/36
Inventor 倪珏萍相君成吕亮洪湖刘吉永邵佳礼周丽琪刘叙杆
Owner CAC NANTONG CHEM
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