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A kind of pyrididine oxime ester compound and its preparation method and application

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 cheap raw materials, good killing activity and simple reaction route

Inactive Publication Date: 2019-01-18
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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  • A kind of pyrididine oxime ester compound and its preparation method and application
  • A kind of pyrididine oxime ester compound and its preparation method and application
  • A kind of pyrididine oxime ester compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0032]

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

[0034] (2) Add 5.0 g (30.1 mmol) of the product obtained in step (1) into a 500 mL round bottom flask, dissolve it with 40 mL of dry DMF, add 1.4 g (36.1 mmol) of sodium hydride and stir for half an hour under ice bath, then add 3...

Embodiment 2

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

[0053] (1) Emulsifiable concentrate: add 1-10g compound CAU-PD-19, 5-15g emulsifier, 0.1-1g penetrant in a 100mL volumetric flask, and then use solvent (such as toluene, xylene, etc.) to make CAU-PD. -19 EC with a mass fraction of 1-10%.

[0054] Other emulsifiable concentrates with the general formula of CAU-PD series compounds can be prepared according to the above methods.

[0055] (2) Wettable powder: take 15-50g compound CAU-PD-19, 10-20g surfactant, 30-75g white carbon black, after mixing and pulverizing, the mass fraction of CAU-PD-19 is 15-50% Wettable powder.

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

Embodiment 3

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

[0058] (1) Test for killing peach aphid: immerse the leaves with green peach aphid in the chemical solution for 5 seconds, and record the number of green peach aphid after drying and put them in a petri dish with moisturizing filter paper. After the petri dish is covered, put 25± In a light incubator at 1°C. Each drug treated more than 30 heads, check the results after 24-48 hours, calculate the corrected mortality (%), and compare with the control drug (pyriproxyfen) to determine the toxicity of the drug. Table 3 shows the insecticidal activity data of the series of compounds with the general formula CAU-PD against Myzus persicae.

[0059] Table 3: Insecticidal activity of CAU-PD series compounds against Myzus persicae

[0060]

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

[0062] From the results in Table 3, the compoun...

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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 particularly relates to a pyriphenone 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 creation of pesticides and medicines due to their high biological activity, good environmental compatibility, and novel target. Pyridine is a very important heterocyclic ring in organic synthesis. It is a biological isostere with benzene, 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, pyridine is a new compound obtained by replacing the benzene ring. It often has the advantages of higher biological activity, systemicity and lower toxicity. [0003] Alkoxypyridine compounds mainly have insecticidal, acaricidal, nematicidal and anti-phytopathog...

Claims

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Application Information

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Patent Type & Authority Patents(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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