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Pyridine-ethylbenzene-ether oxime esterPyrene ethylbenzene oxime-ethers esters compound, and preparation method and application thereof

A technology of pyrididine and compound, which is applied in the field of pyrididine oxime ester compound and its preparation, and achieves the effects of high pesticide research value, simple reaction route, and cheap raw materials

Inactive Publication Date: 2016-04-20
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The oxime ester structure widely exists in various pesticide pharmaceutical molecules, among which trifloxystrobin is a typical representative, but there is no compound containing pyridine, phenyl and oxime ester groups at the same time for the development of pesticides

Method used

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  • Pyridine-ethylbenzene-ether oxime esterPyrene ethylbenzene oxime-ethers esters compound, and preparation method and application thereof
  • Pyridine-ethylbenzene-ether oxime esterPyrene ethylbenzene oxime-ethers esters compound, and preparation method and application thereof
  • Pyridine-ethylbenzene-ether oxime esterPyrene ethylbenzene oxime-ethers esters compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation and structural identification of CAU-PD-19 (R=3-pyridyl) in the pyrididine oxime ester compound (CAU-PD):

[0032]

[0033] In a 250mL round bottom flask, add 10g (82.0mmol) p-Hydroxybenzaldehyde, dissolve in 30mL DMF, then add 22.6g (163.8mmol) potassium carbonate and 12.3g (98.3mmol) 2-bromoethanol, react at 100°C for 12h; TLC ( V (petroleum ether): V (ethyl acetate) = 5: 1) After confirming that the raw materials have reacted completely, cool to room temperature, pour the reaction solution into water, extract 3 times with 200mL ethyl acetate, dry over anhydrous sodium sulfate, concentrate, Column chromatography (V (petroleum ether): V (ethyl acetate) = 10: 1) separated and obtained 11.3 g of a white product with a yield of 83%.

[0034] (2) Add 5.0g (30.1mmol) of the product obtained in step (1) to a 500mL round-bottomed flask, dissolve it with 40mL of dry DMF, add 1.4g (36.1mmol) of sodium hydride in an ice bath and stir for half an hour, t...

Embodiment 2

[0052] Example 2: The preparation method of the CAU-PD-19 (R=phenyl) preparation in the pyrididine oxime ester compound (CAU-PD).

[0053] (1) EC: Add 1-10g of compound CAU-PD-19, 5-15g of emulsifier, 0.1-1g of penetrant into a 100mL volumetric flask, and then dilute to the volume with a solvent (such as toluene, xylene, etc.) to obtain CAU-PD -19 EC with a mass fraction of 1-10%.

[0054] Other emulsifiable concentrates whose general formula is CAU-PD series compounds can be prepared according to the above method.

[0055] (2) Wettable powder: take 15-50g compound CAU-PD-19, 10-20g surfactant, 30-75g white carbon black, mix and pulverize to get CAU-PD-19 mass fraction is 15-50% wettable powder.

[0056] The wettable powders of other series of compounds with general formula CAU-PD can be prepared according to the above method.

Embodiment 3

[0057] Example 3: Determination of the insecticidal and ovicidal activities of a series of compounds with the general formula CAU-PD.

[0058] (1) Peach aphid killing test: soak the leaves with peach aphid in the liquid medicine for 5 seconds, record the number of peach aphids after drying and put them into a petri dish with moisturizing filter paper, put the petri aphid into a 25± in a light incubator at 1°C. Treat more than 30 heads with each drug, check the results after 24-48 hours, calculate the corrected mortality rate (%), and compare it with the control drug (pyriproxyfen) to determine the toxicity of the drug. See Table 3 for the insecticidal activity data of the series of compounds with the general formula CAU-PD against green peach aphid.

[0059] Table 3: Insecticidal activity of compounds with the general formula CAU-PD against peach aphids

[0060]

[0061] Note: the control drug pyriproxyfen and the sample are both 600mg / L

[0062] From the results in Tabl...

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Abstract

The invention discloses a pyridine-ethylbenzene-ether oxime esterpyrene ethylbenzene oxime-ethers esters compound, and a preparation method and application thereof, belonging to the technical field of agricultural chemistry. The preparation method comprises the following steps of adopting p-hydroxy benzaldehyde as a raw material, and reacting with potassium carbonate in DMF (Dimethyl Formamide) to obtain an intermediate product II; reacting enabling the intermediate product II to react with sodium hydride to obtain sodium alkoxide and then reacting with 2-fluoropyridine to obtain an intermediate product III; reacting enabling the intermediate product III to react with pyridine and hydroxylamine hydrochloride in methyl alcohol to obtain an intermediate product IV; reacting enabling the intermediate product IV to react with various carboxylic acid, DCC and pyridine in dichloromethane to obtain the pyridine-ethylbenzene-ether oxime esterpyrene ethylbenzene oxime-ethers esters compound as shown by an end product I. The compound and a preparation thereof provided by the invention has have insecticide and mite ovicidal activity, favorable ovum killing activity, and higher pesticide research value.

Description

technical field [0001] The invention belongs to the technical field of agricultural chemistry, and in particular relates to a pyrididine oxime ester compound and a preparation method and application thereof. Background technique [0002] Heterocyclic compounds, especially nitrogen-containing heterocyclic compounds, have become a research hotspot in the development of pesticides and medicines due to their high biological activity, good environmental compatibility, and novel targets. Pyridine is a very important heterocycle in organic synthesis, and benzene is a bioisostere, but the hydrophobicity of the two is quite different. The hydrophobic constant of benzene is 1.96, and that of pyridine is 0.65. Therefore, the new compound obtained by replacing the benzene ring with pyridine Often have higher biological activity and systemic, lower toxicity and other advantages. [0003] Alkoxypyridine compounds mainly have the activity of killing insects, killing acarids, killing nemat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/78C07D213/64C07D409/12C07D405/12A01N53/00A01N43/40A01N25/02A01N25/14A01P7/04
CPCA01N25/02A01N25/14A01N43/40A01N53/00C07D213/64C07D213/78C07D405/12C07D409/12
Inventor 张建军孙国绍林乐金淑惠王道全
Owner CHINA AGRI UNIV
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