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3,4-dihydropyridine-2-ketone heterocyclic compound and application thereof

A compound, six-membered heterocycle technology, applied in the field of nicotinic compounds, can solve problems such as limited application

Inactive Publication Date: 2010-12-08
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, due to the resistance problem of imidacloprid and the cross-resistance between neonicotinoid insecticides due to structural similarity, the application of this type of compound is limited to a certain extent.

Method used

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  • 3,4-dihydropyridine-2-ketone heterocyclic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Synthesis of compound (Aa-1):

[0093]

[0094] Under nitrogen protection, add 94.38mg (0.39mmol) compound (a-1), 68mg (0.47mmol) compound (b), 1mL anhydrous acetonitrile, 0.05mL (0.47mmol) compound (c) to a 10mL Schlenk tube successively -1), 0.005 mL (0.04 mmol) triethylamine. The temperature of the reaction solution was slowly raised to 80°C-90°C under stirring, and the reaction was stopped after reflux for 4 hours. A large amount of solvent was removed by a rotary evaporator, and the reaction solution was concentrated and then directly separated by column chromatography (eluent: ethyl acetate) to obtain 100 mg of light yellow solid powder. The yield was 69%. Melting point: 213°C-214°C.

[0095] Note: All reagents, reaction vials and condenser tubes in this reaction were dried, and benzaldehyde was redistilled.

[0096] 1H NMR (400MHz, DMSO): δ8.95(s, 1H), 8.17(d, J=2.8Hz, 1H), 7.29-7.26(m, 3H), 7.12(d, J=8.0Hz, 1H), 7.10-7.08(m, 2H), 4.95(t, J=4.4Hz, 1H), 4...

Embodiment 2

[0099] Synthesis of compound (Aa-2):

[0100]

[0101] Under nitrogen protection, add 99.84mg (0.39mmol) compound (a-1), 68mg (0.47mmol) compound (b), 1mL anhydrous acetonitrile, 0.05mL (0.47mmol) compound (c) to a 10mL Schlenk tube successively -2), 0.005 mL (0.04 mmol) triethylamine. The temperature of the reaction solution was slowly raised to 80°C-90°C under stirring, and the reaction was stopped after reflux for 4 hours. A large amount of solvent was removed by a rotary evaporator, and the reaction solution was concentrated and separated by column chromatography (eluent: ethyl acetate) to obtain 96 mg of light yellow solid powder. The yield is 66%. Melting point: 83°C-84°C.

[0102] Note: All reagents, reaction flasks and condenser tubes in this reaction were dried, and furfural was redistilled.

[0103] 1 H NMR (400MHz, DMSO): δ8.95(s, 1H), 8.18(d, J=2.8Hz, 1H), 7.74(d, J=7.2, 1H), 7.21(d, J=8.0Hz, 1H ), 7.10-7.08(m, 2H), 4.89(t, J=3.2Hz, 1H), 4.83(d, J=2.4Hz, 2...

Embodiment 3

[0106] Synthesis of compound (Aa-3):

[0107]

[0108] Under nitrogen protection, add 86.58mg (0.39mmol) compound (a-2), 68mg (0.47mmol) compound (b), 1mL anhydrous acetonitrile, 61.57mg (0.47mmol) compound (c) to a 10mL Schlenk tube successively -3), 0.005 mL (0.04 mmol) triethylamine. The temperature of the reaction solution was slowly raised to 80°C-90°C under stirring, and the reaction was stopped after reflux for 4 hours. A large amount of solvent was removed by a rotary evaporator, and the reaction solution was concentrated and separated by column chromatography (eluent: ethyl acetate) to obtain 112 mg of light yellow solid powder. The yield was 76%. Melting point: 203°C-204°C.

[0109] Note: All reagents, reaction vials and condenser tubes for this reaction were dried.

[0110] 1 H NMR (400MHz, DMSO): δ8.98(s, 1H), 8.28(d, J=2.8Hz, 1H), 7.64(d, J=7.2, 1H), 7.29-7.26(m, 3H), 7.12 (d, J=8.0Hz, 1H), 5.12(t, J=3.2Hz, 1H), 4.86(d, J=2.8Hz, 2H), 3.93-3.83(m, 2H), 2.7...

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Abstract

The invention relates to a nicotine compound and application thereof. The nicotine compound is a 3,4-dihydropyridine-2-ketone heterocyclic compound or an optical isomer, a cis-trans isomer or acceptable salt on the pesticide science thereof. The nicotine compound in the invention has higher insecticidal activity on agroforestry pests, sanitary pests and pests harming the health of animals.

Description

technical field [0001] The present invention relates to a kind of nicotinic compound and its use, in particular to a 3,4-dihydropyridin-2-one heterocyclic compound and its use. technical background [0002] In the past thirty years, the discovery of neonicotinoid insecticides is a milestone innovation in the field of insecticide research. In the mid-1980s, Bayer developed imidacloprid, the first neonicotinoid insecticide, and became one of the most successful new insecticides. Neonicotinoid insecticides represented by imidacloprid have high insecticidal activity, wide insecticidal spectrum, low toxicity to mammals and aquatic animals, good system properties, appropriate field stability and environmental friendliness, and become An important hot spot for the creation of new pesticides. Later, a series of neonicotinoid insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, and dinotefuran were developed successively (European patents 247477, 2...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D405/14C07D471/04A01N43/40A01N43/90A01P7/00A01P7/04
Inventor 李忠邓卫平周懿悦吴宁波徐晓勇须志平
Owner EAST CHINA UNIV OF SCI & TECH
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