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Anthranilic diamide compound containing dichloropropene base and application

A technology of o-formamidobenzamide and dichloropropenyl, applied in the field of o-formamidobenzamide compounds, can solve the problems of reduced productivity and increased consumer costs, achieve high insecticidal activity, and alleviate drug resistance Questions, rich variety of effects

Inactive Publication Date: 2015-12-30
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Invertebrate pest damage to growing and stored crops can cause significant reductions in productivity and consequently increased costs to consumers

Method used

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  • Anthranilic diamide compound containing dichloropropene base and application
  • Anthranilic diamide compound containing dichloropropene base and application
  • Anthranilic diamide compound containing dichloropropene base and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] N-[2-(methylcarbamoyl)-4-chloro-6-methyl-phenyl]-1-(3-chloro-2-pyridyl)-3-[(3,3-dichloropropene Base) Oxygen]-1H-pyrazole-5-carboxamide Synthesis:

[0042] Step A: Synthesis of 2-amino-5-chloro-3-methylbenzoic acid

[0043] Add 2-amino-3-methylbenzoic acid (5g, 33mmol) and DMF20mL into a 50mL three-necked flask, stir to dissolve, the solution is purple, then add NCS (4.4g, 33mmol), and heat the reaction solution to 100°C for 1h , after the completion of the reaction, cool to room temperature, then slowly pour the reaction solution into ice water and keep stirring (purple red solids are precipitated during the process), after stirring for half an hour, suction filter to obtain purple red solid 2-amino-5-chloro-3 -Methylbenzoic acid, weighing 7g after drying.

[0044] Step B: Synthesis of ethyl 1-(3-chloro-2-pyridyl)-3-hydroxy-1H-pyrazole-5-carboxylate

[0045] Add 1-(3-chloro-2-pyridyl)-3-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxylic acid ethyl ester (11 g, 40.7 mmol) ...

Embodiment 2

[0054] N-[2-(cyclopropylcarbamoyl)-4-chloro-6-methyl-phenyl]-1-(3-chloro-2-pyridyl)-3-[(3,3-dichloro Synthesis of propenyl)oxy]-1H-pyrazole-5-carboxamide:

[0055] In a 100 mL round bottom flask, add 1.0 g of 6-chloro-2-[1-(3-chloro-2-pyridyl)-3-[(3,3-dichloropropenyl)oxy]-1H-5- Pyrazolyl]-8-methyl-4H-[d][1,3]benzoxazin-4-one (the product of step D in Example 1), dissolved in 30 mL of acetonitrile (turbid), then add cyclopropylamine solution , the molar ratio was 1:3, and reacted at 30°C for 4h. After the reaction, the solvent was removed under reduced pressure, then dissolved with ethyl acetate, washed with dilute hydrochloric acid, water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the residue was subjected to silica gel column chromatography, and the eluent was a mixed solvent of ethyl acetate and petroleum ether to obtain the target compound.

Embodiment 3

[0057] N-[2-(carbamoyl)-4-chloro-6-methyl-phenyl]-1-(3-chloro-2-pyridyl)-3-[(3,3-dichloropropenyl) Synthesis of oxy]-1H-pyrazole-5-carboxamide:

[0058] In a 100 mL round bottom flask, add 1.0 g of 6-chloro-2-[1-(3-chloro-2-pyridyl)-3-[(3,3-dichloropropenyl)oxy]-1H-5- Pyrazolyl]-8-methyl-4H-[d][1,3]benzoxazin-4-one (the product of Step D of Example 1), dissolved in 30 mL of acetonitrile (turbid), and then added ammonia solution, The molar ratio was 1:3, and the reaction was carried out at 30°C for 4h. After the reaction, the solvent was removed under reduced pressure, then dissolved with ethyl acetate, washed with dilute hydrochloric acid, water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the residue was subjected to silica gel column chromatography, and the eluent was a mixed solvent of ethyl acetate and petroleum ether to obtain the target compound.

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Abstract

The invention discloses an anthranilic diamide compound containing dichloropropene based on a pyrazolone ring and synthesis and application thereof. The structure of the anthranilic diamide compound is shown in the general formula I shown in the specification. The compound is very effective for lepidoptera pests such as plutella xylostella and oriental armyworms and can be used for preparing insecticide in the fields of agriculture and gardening.

Description

technical field [0001] The invention relates to the field of agricultural chemical insecticides, in particular to o-formamidobenzamide compounds. Background technique [0002] Control of invertebrate pests is extremely important in achieving high planting efficiency. Damage to growing and stored crops by invertebrate pests can cause significant reductions in productivity and, consequently, increased costs to consumers. At the same time, the control of pests is also very important in forestry, animal husbandry, sideline, fishery and public health. Although some new pest control agents have appeared on the market, due to the continuous expansion of the market, the resistance of pests, the service life of drugs and other issues and people's increasing emphasis on environmental ecology, scientists need to continue to study, and then develop more effective, Insecticide varieties with low cost, low toxicity, environmental ecological safety and new mode of action. [0003] The r...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/56A01P7/04
CPCC07D401/04A01N43/56
Inventor 王海洋宁斌科毛明珍王威王列平何琦文郑晓蕊魏乐黄晓瑛苏天铎张建功张晓光
Owner XIAN MODERN CHEM RES INST
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