Cis-nitenpyram compound including 1,3-dicarbonyl, preparation method and use

A technology of nitenpyram and dicarbonyl, which is applied in the field of cis-nitenpyram analogs and their preparation, can solve the problems of light instability and poor hydrophobicity, limitations in promotion and application, serious pest resistance, etc. Significant practicability, good insecticidal effect, and short response time

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

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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  • Cis-nitenpyram compound including 1,3-dicarbonyl, preparation method and use
  • Cis-nitenpyram compound including 1,3-dicarbonyl, preparation method and use
  • Cis-nitenpyram compound including 1,3-dicarbonyl, preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Preparation of cis-{3-[N-(6-chloro-3-pyridylmethyl)-N-ethyl]amino-3-N-methylamino-2-nitro-1-(2,4-dichloro phenyl)-allyl}-2,4-pentanedione.

[0047] Add 30mL of absolute ethanol to a 250mL three-necked flask, then add 15mmol of acetylacetone, 15mmol of 2,4-dichlorobenzaldehyde, 10mmol of nitenpyram, and then add 6 drops of piperidine as a catalyst. Heat the round-bottomed three-neck flask containing the above solution in an oil bath, control the temperature at about 78°C, reflux for 6 hours, remove absolute ethanol under reduced pressure, add 10mL of water to dissolve and extract 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=1:2 gave a pale yellow solid with a yield of 82%.

[0048] Elemental analysis: found value C% 55.94 H% 5.28 N% 11.32

[0049] Calculated C% 55.99 H% 5.31...

Embodiment 2

[0053] Preparation of cis-{3-[N-(6-chloro-3-pyridylmethyl)-N-ethyl]amino-3-N-methylamino-2-nitro-1-(3,4-dichloro phenyl)-allyl}-2,4-pentanedione.

[0054] Add 30 mL of absolute ethanol to a 250 mL three-necked flask, then add 15 mmol of malononitrile, 15 mmol of 3,4 dichlorobenzaldehyde, 10 mmol of nitenpyram, and then add 6 drops of piperidine as a catalyst. Heat the round-bottomed three-neck flask containing the above solution in an oil bath, control the temperature at about 78°C, reflux for 6 hours, remove absolute ethanol under reduced pressure, add 10mL of water to dissolve and extract 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=1:1 gave a light yellow solid with a yield of 76.0%.

[0055] Elemental analysis: found value C% 52.28 H% 4.74 N% 10.62

[0056] Calculated C% 52...

Embodiment 3

[0060] Preparation of cis-{3-[N-(6-chloro-3-pyridylmethyl)-N-ethyl]amino-3-N-methylamino-2-nitro-1-phenyl-allyl} -2,4-pentanedione.

[0061] Add 30 mL of absolute ethanol to a 250 mL three-necked flask, then add 15 mmol of acetylacetone, 15 mmol of benzaldehyde, and 10 mmol of nitenpyram in sequence, and then add 6 drops of piperidine as a catalyst. Heat the round-bottomed three-neck flask containing the above solution in an oil bath, control the temperature at about 78°C, reflux for 6 hours, remove absolute ethanol under reduced pressure, add 10mL of water to dissolve and extract 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=1:1 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] Calculated C% 51.08 H% 3.88 N...

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PUM

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Abstract

The invention discloses a cis-nitenpyram compound including 1,3-dicarbonyl, a preparation method and use. The structural general formula (I) of the cis-nitenpyram compound including 1,3-dicarbonyl is as follows: FORMULA. The preparation method comprises the following steps of: back flowing, heating and reacting a 1,3-dicarbonyl compound, aromatic aldehyde, nitenpyram and piperidine. The compound disclosed by the invention has the advantages that: the compound has efficient insecticidal activity, good desinsection effect and low toxicity; the compound is safe for human and animal and can promote the growth of crops; the use method is simple and convenient; the preparation method is simple; and the reaction time is short.

Description

technical field [0001] The invention belongs to pesticides and insecticides, in particular to a class of 1,3-dicarbonyl-containing cis-nitenpyram analogues with insecticidal activity and their preparation. 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 pesticide required by mod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61A01N43/40A01P7/04
Inventor 薛思佳吴颖
Owner SHANGHAI NORMAL UNIVERSITY
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