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M-diamide compound and preparation method and application thereof

A technology of isodiamide and compound, which is applied in the field of compound and its preparation in which the 3-position of isodiamide is substituted by N-cyclopropylmethyl derivatives, can solve the problems of poor quick-acting property and poor insecticidal effect, and achieve High insecticidal activity, fast onset, and reduced dosage

Active Publication Date: 2019-03-22
CAC NANTONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These disclosed compounds are insecticidally active, however at low doses they are not effective or readily available

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0155] N-[2-Bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-(trifluoromethyl)phenyl]-3-[N- (Cyclopropylmethyl)-benzamido]-2-fluorobenzamide (compound No. 4):

[0156] (1) Synthesis of 2-fluoro-[3-(cyclopropylmethyl)amino]benzoic acid methyl ester

[0157]

[0158] 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 product ...

Embodiment 2

[0171] N-[2-Bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-(trifluoromethyl)phenyl]-3-[N- (Cyclopropylmethyl)-4-cyanobenzamido]-2-fluorobenzamide (compound number 23):

[0172] (1) Synthesis of methyl 2-fluoro-3-[N-(cyclopropylmethyl)-4-cyanobenzamido]benzoate

[0173]

[0174] 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 ethyl acetate (20 ...

Embodiment 3

[0184] N-[2-Bromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)-6-(trifluoromethyl)phenyl]-3-[N- Preparation of (cyclopropylmethyl)-4-(trifluoromethyl)benzamido]-2-fluorobenzamide (compound number 37):

[0185]

[0186] (1) Add 2-fluoro-3-[N-(cyclopropylmethyl)-4-trifluoromethylbenzamide]benzoic acid (0.45g, 1.12mmol) and toluene (6mL) successively to the reaction flask, Thionyl chloride (0.67 g, 5.60 mmol) 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 further use.

[0187] (2) Dissolve 2-bromo-6-trifluoromethyl-4-heptafluoroisopropylaniline (0.46g, 1.12mmol) in tetrahydrofuran (4mL), and add lithium diisopropylamide dropwise at -70°C (0.70mL, 1.42mmol), after 5min, add the tetrahydrofuran solution to be used dropwise, stir at -70°C for 30min, warm to room temperature and continue stirring for 30min. When TLC monitors that the reaction no longer proceeds, the reactio...

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PUM

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Abstract

The invention provides an m-diamide compound and a preparation method and application thereof. The m-diamide compound has a structure as shown in a formula I. The m-diamide compound has high insecticidal activity at a low dosage, is quick to take effect, can exert the insecticidal activity if being applied one day, can reach very high insecticidal activity if being applied three days, and has a good quick effect. As the m-diamide compound is good in effect at the low dosage, damage to plants and human as the drug concentration is too high is reduced, and generated drug residues are few duringapplication, so that the m-diamide compound is more environment-friendly and wide in application prospect.

Description

technical field [0001] The present invention belongs to the field of insecticides, and relates to a methanediamide compound and its preparation method and application, in particular to a compound whose 3-position of methanediamide is substituted by an N-cyclopropylmethyl derivative, and its preparation method and application . Background technique [0002] In the production of crops such as agriculture and horticulture, the damage caused by 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 better activity and lower dosage. , New insecticides that are more environmentally friendly. [0003] The insecticidal activity of intermediate diamide compounds has been reported, as CN102119143A discloses compound KC1 (i.e. compound 7-1574 in CN102119143A) and KC2 (i.e. compound 7-1595 in CN102119143A) and its insecticidal activity, wherein KC1 has been commercia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N37/46A01N41/10A01N37/48A01P7/04
CPCA01N37/18A01N37/34A01N43/82C07C237/42C07C255/50C07D271/06C07C2601/02C07C233/88C07C255/57A01N37/46A01N37/48A01N41/10
Inventor 吕亮刘吉永相君成马文静周丽淇侯爽倪珏萍李宗成
Owner CAC NANTONG CHEM
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