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1,4-dihydropyridine ring-containing cis-neonicotinoid compounds and preparation thereof

A technology of dihydropyridine rings and neonicotinoids, which is applied in the fields of botany equipment and methods, organic chemistry, animal repellants, etc., and can solve the problems of popularization and application limitations, light instability and poor hydrophobicity, and pest resistance Serious and other problems, to achieve the effect of good insecticidal effect, significant practicability, and short reaction time

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

However, due to the shortcomings of light instability and poor hydrophobicity, the promotion and application are limited; meanwhile, the resistance of pests to it is becoming more and more serious

Method used

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  • 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds and preparation thereof
  • 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds and preparation thereof
  • 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Preparation of cis-1-methyl-4-(4-chlorophenyl)-3-cyano-2-amino-6-[N-(6-chloro-3-pyridylmethyl)-N-ethyl]amino -5-nitro-1,4-dihydropyridine.

[0046] Add 30 mL of absolute ethanol to a 250 mL three-necked flask, then add 12 mmol of malononitrile, 12 mmol of p-chlorobenzaldehyde, and 10 mmol of nitenpyram in sequence, and then add 6 drops of piperidine as a catalyst. Put the round-bottomed three-neck flask containing the above solution into a microwave reactor, control the temperature at about 65°C, microwave for 30 minutes, remove absolute ethanol under reduced pressure, add 10 mL of water to dissolve and extract three times with 60 mL 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=3:1 gave a light yellow solid with a yield of 85.5%.

[0047] Elemental analysis: found value C% 54.80 H% 4.25 N% 18.35

[0048] ...

Embodiment 2

[0053] Preparation of cis-1-methyl-4-phenyl-3-cyano-2-amino-6-[N-(6-chloro-3-pyridylmethyl)-N-ethyl]amino-5-nitro- 1,4-Dihydropyridine.

[0054]Add 30 mL of absolute ethanol to a 250 mL three-necked flask, then add 12 mmol of malononitrile, 12 mmol of benzaldehyde, and 10 mmol of nitenpyram in sequence, and then add 6 drops of piperidine as a catalyst. Put the round-bottomed three-neck flask containing the above solution into a microwave reactor, control the temperature at about 65°C, microwave for 30 minutes, remove absolute ethanol under reduced pressure, add 10 mL of water to dissolve and extract three times with 60 mL 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=3:1 gave a pale yellow solid with a yield of 86.0%.

[0055] Elemental analysis: found value C% 59.28 H% 4.34 N% 19.62

[0056] Calculated...

Embodiment 3

[0060] Preparation of cis-1-methyl-4-(2,4-dichlorophenyl)-3-cyano-2-amino-6-[N-(6-chloro-3-pyridylmethyl)-N- Ethyl]amino-5-nitro-1,4-dihydropyridine.

[0061] Add 30 mL of absolute ethanol to a 250 mL three-necked flask, then add 12 mmol of malononitrile, 12 mmol of 2,4-dichlorobenzaldehyde, 10 mmol of nitenpyram, and then add 6 drops of piperidine as a catalyst. Put the round-bottomed three-neck flask containing the above solution into a microwave reactor, control the temperature at about 65°C, microwave for 30 minutes, remove absolute ethanol under reduced pressure, add 10 mL of water to dissolve and extract three times with 60 mL 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=3:1 gave a light yellow solid with a yield of 79.1%.

[0062] Elemental analysis: found value C% 50.57 H% 3.67 N% 17.08

[0063] ...

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Abstract

The invention belongs to pesticides, in particular to 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds and preparation thereof. Nitenpyram has the disadvantages of optical instability and poor hydrophobicity. The 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds have the structural general formula (I) shown in the specification. The preparation method of the 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds comprises the following steps of: adding the solution of ethanol or acetonitrile into a round bottom three-neck flask; adding malononitrile, aromatic aldehyde and nitenpyram into the solution of the ethanol or the acetonitrile; adding catalyst piperidine, wherein the nitenpyram, the malononitrile and the aromatic aldehyde are in the molar ratio of 1:1.2:1.2; and placing the round bottom three-neck flask filled with the mixed solution into a microwave reactor for performing a microwave reaction for 30 minutes at the temperature of 65 DEG C to prepare the 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds having the general formula (I). The 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds have the advantages that: the 1,4-dihydropyridine ring-containing cis-neonicotinoid compounds have high-efficiency insecticidal activity, a good insecticidal effect, low toxicity, people and livestock safety, a simple and convenient using method, a simple preparation method, and short reaction time.

Description

technical field [0001] The invention belongs to pesticides and insecticides, in particular to a class of cis-neonicotinoid compounds with insecticidal activity containing 1,4-dihydropyridine ring and the preparation thereof. Background technique [0002] The discovery of neonicotinoid insecticides can be considered a milestone in agrochemical research over the past three decades. Neonicotinoid insecticides are the fourth generation of insecticides following organophosphorus, carbamate, and pyrethroid insecticides. As nicotinic acetylcholine receptors (nAChRs) agonists that act selectively on the nervous system (nAChRs) of insects, neonicotinoids not only show high affinity for (nAChRs), but also show non-ionizing Physicochemical properties such as high temperature resistance and moderate water solubility. Because of its unique insecticidal mechanism and high efficiency and low toxicity performance, it has quickly become a new type of high efficiency and low toxicity pestic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A01N43/40A01P7/04
Inventor 薛思佳陈燕霞
Owner SHANGHAI NORMAL UNIVERSITY
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