O-formammidotiazol-benzamide derivatives based on ryanodine receptor, and preparation method and applications thereof

A technology of o-formamidobenzamide and derivatives, applied in the field of o-formamidobenzamide derivatives, can solve problems such as the limited number of pesticide varieties

Inactive Publication Date: 2014-02-26
JIANGXI TIANREN ECOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although bisamide insecticides have shown outstanding advantages in terms of activity, pests have shown varying degrees of resistance due to frequent over-application in some areas, and the number of commercialized varieties of this type of insecticides is very limited so far.

Method used

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  • O-formammidotiazol-benzamide derivatives based on ryanodine receptor, and preparation method and applications thereof
  • O-formammidotiazol-benzamide derivatives based on ryanodine receptor, and preparation method and applications thereof
  • O-formammidotiazol-benzamide derivatives based on ryanodine receptor, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1: 3-Bromo-1-(3-chloropyridin-2-yl)-N-(4-cyano-2-(methoxycarbamoyl)-6-methylphenyl)-1H- Preparation of pyrazole-5-carboxamide (Compound I-10)

[0059]

[0060] Compound I-10 can be prepared by the following method, and the specific steps are as follows:

[0061]

[0062] Preparation of intermediate 3-bromo-1-(3-chloro-pyridyl)-1H-pyrazole-5-carboxylic acid III-1

[0063]

[0064] Preparation of 2-(3-bromo-pyrazol-1-yl)-3-chloropyridine:

[0065] 3-Bromo-1H-pyrazole was dissolved in DMF (80 mL), 2,3-dichloro-pyridine (13.8 g) and potassium carbonate (57.3 g) were added, and the mixture was stirred at 100°C for 8 hours. After adding water, the mixture was extracted twice with ethylamine, and the combined organic layer was washed twice with water and brine, and then washed with Na 2 SO 4 Dry and concentrate in vacuum. The residue was purified by column chromatography (propylamine / ethylamine 6:1) to obtain 7 g of the title compound 2-(3-bromo-pyrazol-1-yl)-3-chloropyridin...

Embodiment 2

[0079] Example 2: 3-Bromo-N-(4-chloro-2-methyl-6-(carboxycarbamoyl)phenyl)-1-(3,5-dichloropyridin-2-yl)-1H- Preparation of pyrazole-5-carboxamide (Compound I-2)

[0080]

[0081] Compound I-2 can be prepared by the following method, and the specific steps are as follows:

[0082] Preparation of 2-(3-bromo-1H-pyrazol-1-yl)-3,5-dichloropyridine:

[0083]

[0084] This compound is carried out in the same way as the preparation of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine, which is prepared from 3-bromo-1H-pyrazole and 2,3,5-trichloropyridine To prepare.

[0085] Preparation of 3-bromo-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid (III-2):

[0086]

[0087] Compound III-2 was prepared from 2-(3-bromo-1H-pyrazol-1-yl)-3,5-dichloropyridine and carbon dioxide using the same method as preparation III-1.

[0088] Preparation of 2-amino-5-chloro-3-methylbenzoic acid (Compound IV-2):

[0089] Use the same method for preparing 2-amino-5-iodo-3-methylbenzoic acid, in which N-chlorosu...

Embodiment 3

[0096] Example 3: 3-Bromo-1-(3-chloropyridin-2-yl)-N-(4-cyano-2-(hydroxycarbamoyl)-6-methylphenyl)-1H-pyrazole Preparation of -5-carboxamide (Compound I-9):

[0097]

[0098] Compound I-9 was prepared from Intermediate V-1) through the above route using the same steps as Preparation Example 1, and the reagent compound VI) was prepared with NH 2 OH·HCl instead of CH 3 ONH 2 ·HCl.

[0099] To 2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-8-methyl-4-oxo-4H-benzo[d][1 , 3] Oxazine-6-carbonitrile (V-1) (50 mg, 0.11 mmol) dissolved in CH 3 Add NH to the solution in CN (5mL) 2 OH·HCl (159.8 mg, 2.3 mmol) and Et 3 N (319.3uL, 2.3mmol), stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filtrate was concentrated in vacuo and subjected to flash chromatography (dichloromethane: methanol = 10:1) to obtain a colorless solid (15 mg, yield: 28%); 1 H NMR(DMSO-d 6 , 300MHz), δ: 2.14 (s, 3H), 7.36 (s, 1H), 7.61-7.65 (dd, 1H, J = 7.8 Hz, J = 4.8 Hz), 7.75 (s, ...

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Abstract

The invention provides o-formammidotiazol-benzamide derivatives, and a preparation method and applications thereof. The o-formammidotiazol-benzamide derivatives have the chemical structure general formula represented by the formula I or the formula II. The invention discloses the structure general formula of the compounds, the synthesis method and the applications of the compounds as insecticides, acaricides and bactericides; the compounds are mixed with agriculturally acceptable auxiliary agents or synergistic agents for use in processing crafts of preparing the insecticides, the acaricides and the bactericides. The invention also discloses the applications of the compounds in combination with the commercial insecticides, the acaricides, the bactericides, anti-plant virus agents and plant activators for prevention and treatment of agriculture, forestry, horticulture plant diseases, insect attacks, acarus attacks and virus diseases, and the preparation method of the compounds.

Description

Technical field [0001] The present invention relates to certain o-formylaminobenzamide derivatives, to methods for preparing them, to their use as active agents for insecticides, acaricides and fungicides, and to the use of these compounds and their The method and application of the composition in the prevention and control of pests, mites, diseases and virus diseases in agriculture, forestry and horticulture environments. Background technique [0002] Harm to growing crops and stored crops by pests will result in a significant decrease in yield, which in turn will increase production costs. Pest control is very important in forestry, greenhouse crops, ornamental plants, crop seedlings, stored food and fiber products, animal husbandry, households, lawns, wood products, and sanitation. The new super efficient insecticide bisamide has a novel structure, unique mechanism of action, and is safe for mammals. The main phthalimide insecticides are flubendiamide (EP1006107); phthalimide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D409/14C07D405/14C07D401/14A01N43/40A01P1/00A01P3/00A01P7/02A01P7/04
CPCA01N43/56C07D401/04C07D401/14C07D405/14C07D409/14
Inventor 梁小文王根豪陈晓燕李源刘丽君朱湘盛程学恒房丽燕李娜周晶董婧刘智潇叶志雄蔡建华谢东升刘井宝傅磊马忠岩李肖宇周立峰曾升华曾繁富肖筱成熊建生
Owner JIANGXI TIANREN ECOLOGY
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