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Cis nitenpyram analog containing 1,4-dihydropyridine ring and preparation method thereof

A technology of dihydropyridine ring cis-nitenpyram and dihydropyridine ring, which is applied in the field of pesticides and insecticides, can solve the problems of light instability and poor hydrophobicity, and achieve simple use, low toxicity and high efficiency The effect of insecticidal activity

Inactive Publication Date: 2011-05-25
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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  • Cis nitenpyram analog containing 1,4-dihydropyridine ring and preparation method thereof
  • Cis nitenpyram analog containing 1,4-dihydropyridine ring and preparation method thereof
  • Cis nitenpyram analog containing 1,4-dihydropyridine ring and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: cis-1-methyl-4-phenyl-3-ethoxycarbonyl-2-amino-6-[N-(6'-chloro-3'-pyridylmethyl)-N-ethyl] Amino-5-nitro-1,4-dihydropyridine (Ia);

[0041] Dissolve benzaldehyde (1.06g, 10mmol) in absolute ethanol (30mL) at room temperature, add ethyl cyanoacetate (1.4ml, 10mmol), add a catalytic amount of piperidine dropwise, 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%.

[0042] Elemental Analysis: Calculated C% 58.53 H% 5.55 N% 14.84

[0043] ...

Embodiment 2

[0049] 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);

[0050] Dissolve p-bromobenzaldehyde (1.83g, 10mmol) in absolute ethanol (30mL) at room temperature, add ethyl cyanoacetate (1.4ml, 10mmol), add a catalytic amount of piperidine dropwise 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 evaporated 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%.

[0051] Elemental analysis: found value C% 50.18 H% 4.54...

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 a catalytic amount of piperidine dropwise 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 C% 54.49 H% 4.98 ...

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Abstract

The invention belongs to a pesticide, in particular to a cis nitenpyram analog containing 1,4-dihydropyridine ring and a preparation method thereof. The application of the existing nitenpyram pesticide is limited because of light instability and poor hydrophobicity. The cis nitenpyram analog containing the 1,4-dihydropyridine ring has the general formula (I). The preparation method comprises the following steps: adding alcohol or acetonitrile in a round-bottomed three-necked flask to serve as solvent; adding ethyl cyanoacetate, aromatic aldehyde, nitenpyram and catalyst piperidine, wherein the molar ratio of the nitenpyram to the ethyl cyanoacetate to the aromatic aldehyde is 1:1.2:1.2; heating and warming to 65DEG C; carrying out reflux reaction for 12-16 hours; and preparing the cis nitenpyram analog containing 1,4-dihydropyridine ring, which has the general formula (I). The cis nitenpyram analog containing 1,4-dihydropyridine ring has the advantages of good insecticidal effect, low toxicity and short reaction time and is convenient to use and simple in operation, is safe for people and livestock, and accelerates the growth of crops.

Description

technical field [0001] The invention belongs to pesticides and insecticides, in particular to a class of neonicotinoid insecticides containing 1,4-dihydropyridine rings and cis-nitenpyram containing 1,4-dihydropyridine rings. Analogues and preparation methods. 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 high efficiency, broad spectrum and good root sy...

Claims

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Application Information

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