Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof

A technology of o-formamidobenzamide and monofluoromethoxypyrazole, applied in the field of o-formamidobenzamide compounds

Active Publication Date: 2013-06-05
SINOCHEM LANTIAN +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many products are commercially available for the control of invertebrate pests, there is still a need for new compounds that are more effective, less toxic, lower cost, and environmentally safe

Method used

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  • Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof
  • Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof
  • Fluoro methoxylpyrazole-containing o-formylaminobenzamide compound, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] Example 1N-[2-(tert-butylcarbamoyl)-4-chloro-6-methyl-phenyl]-1-(3-chloro-2-pyridyl)-3-fluoromethoxy- Synthesis of 1H-pyrazole-5-carboxamide (compound 8)

[0139] Step 1: Synthesis of 3-fluoromethoxy-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid

[0140] In a 500ml three-neck round bottom flask, add 1-(3-chloro-2-pyridyl)-3-hydroxyl-1H-pyrazole-5-carboxylic acid ethyl ester (13.35g, 0.05mol), 300ml acetonitrile, solid carbonic acid Potassium (8.28g, 0.06mol), bromofluoromethane (8.48g, 0.075mol), then heated to reflux, reacted until the raw materials completely disappeared, cooled to room temperature, filtered, the filter cake was rinsed with acetonitrile 2*50ml, and the filtrate was concentrated Add 200ml of methanol to dissolve it, then slowly add 50ml of aqueous solution containing sodium hydroxide (2.4g, 0.06mol) dropwise at room temperature, stir at room temperature for about 30min, the reaction is complete, distill off the solvent, add water, and diethyl e...

Embodiment 2

[0145] Example 2N-[2-(methylcarbamoyl)-4-chloro-6-methyl-phenyl]-1-(3-chloro-2-pyridyl)-3-fluoromethoxy-1H- Synthesis of Pyrazole-5-Carboxamide (Compound 3)

[0146] In a 50ml single-necked round bottom flask, add 6-chloro-2-[3-fluoromethoxy-1-(3-chloro-2-pyridyl)-1H-5-pyrazolyl]-8-methyl Add methylamine hydrochloride (0.19g, 0.00286mol) and anhydrous sodium acetate (0.24g, 0.00286mol), after stirring overnight at room temperature, the reaction was complete, the THF was evaporated under reduced pressure, water was added to the residue, extracted with ethyl acetate, and the organic phase was dried with anhydrous sodium sulfate. Filtration, concentration to obtain a crude product, and recrystallization with ethanol to obtain 0.87 g of a white solid, which is N-[2-(methylcarbamoyl)-4-chloro-6-methyl-phenyl]-1-(3-chloro -2-pyridyl)-3-fluoromethoxy-1H-pyrazole-5-carboxamide, melting point 236.0-237.4°C, yield 82.7%; 1 HNMR (400MHz, DMSO-d 6 )δ2.18(s, 3H), 2.93-2.94(d, 2H), 5.83...

Embodiment 3

[0147] Example 3N-[2-(ethylcarbamoyl)-4-cyano-6-methyl-phenyl]-1-(3-chloro-2-pyridyl)-3-fluoromethoxy-1H -Synthesis of pyrazole-5-carboxamide (compound 33)

[0148] The first step: 6-cyano-2-[3-fluoromethoxy-1-(3-chloro-2-pyridyl)-1H-5-pyrazolyl]-8-methyl-4H-[ d] Synthesis of [1,3] benzoxazin-4-one

[0149]In a 250ml three-neck round-bottomed flask, 3-fluoromethoxy-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid (5g, 0.0185mol) (Example 1-Synthesis No. One-step product), 2-amino-5-cyano-3-methylbenzoic acid (3.24g, 0.0185mol), acetonitrile 150ml, pyridine 15ml, stirring to dissolve all the solids, cooling the system, at -5°~- Add methanesulfonyl chloride (4ml, 5.98g, 0.052mol) / 20ml of acetonitrile solution dropwise at 10°. After the dropwise addition, keep it at -5°~-10° for 1h, then naturally rise to room temperature for 3h, after the reaction is complete , add 30ml of water, stir for 30min, filter, filter the cake successively with 2:1 acetonitrile / water (2*40ml), ac...

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Abstract

Fluoromethoxypyrazole anthranilamide compounds of formula (I) or agrochemical salts thereof, as well as synthesization methods and uses thereof. The compounds of formula (I) have broad-spectrum insecticidal activities and are effective to pests of lepidopteron (such as Plutella xylostella), hemipteran (such as Aphis medicaginis), homopteran (such as Nilaoarvata lugens) and the like. Agricultural preparations including compounds of formula (I) and methods of preventing and controlling pests are involved.

Description

technical field [0001] The invention provides an o-formamidobenzamide compound. Background technique [0002] O-formamidobenzamide compounds (ryanodine receptor inhibitors) are effective insecticides developed in recent years to control invertebrate pests. [0003] PCT patent application WO2003 / 015519 discloses the following compounds having insecticidal activity: [0004] [0005] R=CF 3 , Cl, Br or OCH 2 CF 3 [0006] PCT patent application WO2004 / 033468 discloses the following compounds having insecticidal activity: [0007] [0008] PCT patent application WO2004 / 067528 discloses the following compounds with insecticidal activity: [0009] [0010] PCT patent application WO2006 / 080311 discloses the following compounds with insecticidal activity: [0011] [0012] PCT patent application WO2006 / 023783 discloses the following compounds with insecticidal activity: [0013] [0014] PCT patent application WO2008 / 134969 discloses the following compounds w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D231/22C07D413/14C07D413/12A01N43/56A01P7/04A01P7/02
CPCC07D401/14C07D413/14C07D231/22C07D413/12C07D401/04A01N43/56
Inventor 窦花妮陈杰郑昀红许天明刑家华郑志文彭伟立许勇华董德臻魏优昌孔小林袁静刘刚
Owner SINOCHEM LANTIAN
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