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1,4- dihydropyridine ring-containing cis-nitenpyram compound, preparation method and application thereof

A dihydropyridine ring cis-nitenpyram and compound technology, which is applied in the field of cis-nitenpyram compounds and their preparation, can solve problems such as poor hydrophobicity and light instability, achieve low toxicity, and use methods Simplicity and significant practical effect

Inactive Publication Date: 2011-11-02
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But its application is limited by its photoinstability and poor hydrophobicity

Method used

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  • 1,4- dihydropyridine ring-containing cis-nitenpyram compound, preparation method and application thereof
  • 1,4- dihydropyridine ring-containing cis-nitenpyram compound, preparation method and application thereof
  • 1,4- dihydropyridine ring-containing cis-nitenpyram compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] cis-1-methyl-4-phenyl-3-ethoxycarbonyl-2-amino-6-[N-(6'-chloro-3'-pyridylmethyl)-N-ethyl]amino-5- Nitro-1,4-dihydropyridine (Ia);

[0043] Dissolve benzaldehyde (1.06g, 10mmol) in absolute ethanol (30mL) at room temperature, add ethyl cyanoacetate (1.4ml, 10mmol), add dropwise 0.5ml of piperidine and stir at room temperature for 2 hours, then add The compound nitenpyram (10mmol, 2.707g) was heated to reflux, and the reaction was tracked by TLC. After the reaction was completed, it was cooled, and the solvent was distilled off under reduced pressure, dissolved in 10mL of water and extracted three times with 60mL of ethyl acetate. The combined extracts were dried overnight with anhydrous magnesium sulfate, and the solvent was distilled off to obtain a yellow oil. Column chromatography with ethyl acetate:petroleum ether=2:1 gave a yellow solid with a yield of 81.23%.

[0044] Elemental Analysis: Calculated C% 58.53 H% 5.55 N% 14.84

[0045] Measured value C% 58.12 H% 6....

Embodiment 2

[0050] Preparation of cis-1-methyl-4-(4'-bromophenyl)-3-ethoxycarbonyl-2-amino-6-[N-(6'-chloro-3'-pyridylmethyl)-N- Ethyl]amino-5-nitro-1,4-dihydropyridine (Ib);

[0051] Dissolve p-bromobenzaldehyde (1.83g, 10mmol) in absolute ethanol (30mL) at room temperature, add ethyl cyanoacetate (1.4ml, 10mmol), dropwise add 0.5ml of piperidine and stir at room temperature for 2 hours, Then the compound nitenpyram (10mmol, 2.707g) was added and heated to reflux, and the reaction was tracked by TLC. After the reaction was completed, it was cooled, and the solvent was distilled off under reduced pressure, dissolved in 10mL of water and extracted three times with 60mL of ethyl acetate. The combined extracts were dried overnight with anhydrous magnesium sulfate, and the solvent was distilled off to obtain a yellow oil. Column chromatography with ethyl acetate:petroleum ether=2:1 gave a yellow solid with a yield of 51.73%.

[0052] Elemental analysis: found value C% 50.18 H% 4.54 N% 12.74 ...

Embodiment 3

[0058] Preparation of cis-1-methyl-4(-2'-chlorophenyl)-3-ethoxycarbonyl-2-amino-6-[N-(6'-chloro-3'-pyridylmethyl)-N- Ethyl]amino-5-nitro-1,4-dihydropyridine (Ic);

[0059] Dissolve 2-chlorobenzaldehyde (1.41g, 10mmol) in absolute ethanol (30mL) at room temperature, add ethyl cyanoacetate (1.4ml, 10mmol), add dropwise 0.5ml of piperidine and stir at room temperature for 2 hours , then add the compound nitenpyram (10mmol, 2.707g) and heat to reflux, TLC tracking reaction, after the reaction is cooled, evaporate the solvent under reduced pressure, add 10mL water to dissolve and extract three times with 60mL ethyl acetate. The combined extracts were dried overnight with anhydrous magnesium sulfate, and the solvent was distilled off to obtain a yellow oil. Column chromatography with ethyl acetate:petroleum ether=2:1 gave a yellow solid with a yield of 65.49%.

[0060] Elemental Analysis: Calculated C% 54.55 H% 4.98 N% 13.83

[0061] Found value C% 54.49 H% 4.98 N% 13.96

[0062...

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Abstract

The invention belongs to agricultural insecticide, and discloses a 1,4- dihydropyridine ring-containing cis-nitenpyram compound, a preparation method and an application thereof. A structure of the compound is represented by a general formula (I). The preparation method is characterized by: adopting alcohol or methyl cyanides as a solvent and adding cyanoacetate, aromatic alcohol and nitenpyram; adding a catalyst of piperidine; carrying out a reflux reaction for 12-16 hours. The 1,4- dihydropyridine ring-containing cis-nitenpyram prepared from the method can be adopted as a insecticide. The 1,4- dihydropyridine ring-containing cis-nitenpyram compound provided by the present invention has advantages of good insecticidal effect, low toxicity, safety for human and livestocks, improvement for crop growth, convenient operation, short reaction time and simple preparation.

Description

technical field [0001] The invention belongs to pesticides and insecticides, in particular to a class of neonicotinoid insecticides containing 1,4-dihydropyridine rings with insecticidal activity, especially cis-enes containing 1,4-dihydropyridine rings Acetamid compound, preparation method and application. Background technique [0002] Neonicotinoid insecticides are the fourth generation of insecticides following organophosphorus, carbamate, and pyrethroid insecticides. Neonicotinoids are highly active insecticides with low toxicity to mammals. The main reason is that it has a strong electronegative pharmacophore, including nitroguanidine, nitrosoimino, cyanourea, etc. Compounds with these pharmacophore can selectively interact with the unique nAChR subunit of insects. type interaction without vertebrate α 4 beta 2 nAChR role. Due to the unique mechanism of action of this type of insecticide, there is no cross-resistance with conventional insecticides. It not only has ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D405/14A01N43/40A01P7/04
Inventor 薛思佳刘天雁
Owner SHANGHAI NORMAL UNIVERSITY