Preparation method and use of compound with high insecticidal activity

A compound and plant technology, applied in the field of nitromethylene derivatives, can solve the problems of complex preparation process, high cost and the like

Inactive Publication Date: 2007-10-03
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preferred compound preparation process in the above-mentioned patent application is relatively complicated and expensive, thus limiting the application of these compounds

Method used

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  • Preparation method and use of compound with high insecticidal activity
  • Preparation method and use of compound with high insecticidal activity
  • Preparation method and use of compound with high insecticidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] 1-(6-Chloro-3-methylpyridinyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine- Synthesis of 5-alcohol (Compound 1):

[0069] (1) Synthesis of 2-nitro-ethylene-1,1-disulfide potassium

[0070]

[0071] Put 4.0g (0.03mol) of nitromethane and 6ml (0.05mol) of carbon disulfide in a 100ml three-necked flask, add 10ml of ethanol as a solvent, and start stirring. Weigh 8g (0.14mol) of potassium hydroxide and dissolve it with 40ml of ethanol, and slowly add it dropwise to the above solution at room temperature (about 30min). Because the reaction process is exothermic, the dropping rate depends on the reaction temperature at the time, and the temperature should be controlled between 30 and 35°C. After the addition is complete, let the reaction continue to stir for 2 hours. Finally, the solid was filtered out, and the crude product was obtained as a brown-yellow powdery solid with a yield of 72%.

[0072] (2) Synthesis of 1,1-Dithiomethyl-2-nitroethylene

[0073]

...

Embodiment 2

[0089] 1-(6-Chloro-3-methylpyridyl)-5-methoxy-7-methyl-8nitro-1,2,3,5,6,7-hexahydroimidazole [1,2- ] Synthesis of Pyridine (Compound 2)

[0090] (1) Synthesis of 1,1-dichloro-2-nitroethylene

[0091]

[0092] In a three-necked flask equipped with stirring, a mixture of 20.85 g (0.2055 mol) of 36% hydrochloric acid and 19.9 g (0.2055 mol) of 65% nitric acid was added. 15.5g (0.1575mol) of vinylidene chloride was added dropwise, the temperature of the dropwise addition was controlled between 20-25°C, and the temperature was kept and stirred for 3 hours. Add 50ml of dichloromethane to extract, wash with water, and control the pH of the oil layer to about 3-4. Add 5-6 grams of alkali to 120ml of water to dissolve, cool to 0°C, gradually add to the oil layer, and keep the temperature at 0°C. After the addition is complete, stir vigorously for another 5 minutes. Extraction with dichloromethane, separate layers, wash the oil layer with water, dry and filter to obtain about 13.5-17.5 g ...

Embodiment 3

[0107] 1-(6-Chloro-3-methylpyridinyl)-5-ethoxy-7-methyl-8nitro-1,2,3,5,6,7-hexahydroimidazole [1,2- ] The synthesis of pyridine (compound 3), the reaction equation is as follows:

[0108]

[0109] Combine 10.16g (0.04mol) of 2-chloro-5-(2-nitromethylene-imidazolidine-1-ylmethyl)-pyridine, 100ml of absolute ethanol, about 5ml of crotonaldehyde, catalytic amount of AcOH Placed in a 250ml round-bottomed flask, refluxed, TLC followed the reaction, after the reaction, the solvent was removed, column chromatography was separated to obtain a pure yellow powder, and the pure product was separated by column chromatography as a yellow powder solid with a yield of 75 %, mp = 138.8-140.3°C. 1 H NMR(500MHz, CDCl 3 ): 8.31(d, J=2Hz, 1H, pyridine-H), 7.87(dd, J 1 = 2Hz, J 2 = 8Hz, 1H, pyridine-H), 7.33 (d, J=8Hz, 1H, pyridine-H), 4.76 (dd, J 1 =15Hz, J 2 =15Hz, 2H, -CH 2 -N-), 4.56(t, J 1 =3Hz, J 2 = 3Hz, 1H, -CHO-), 3.60 (m, 4H, imidazolidine-H), 3.57 (m, 2H, -O-CH 2 -), 3.53(m, 1H, -CHCH 2 -...

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Abstract

This invention relates to a kind of nitryl methylene ramification, and its preparation method and application. Anthelminthic activity test indicate: this ramification has very high insecticidal activity to thorn-suck type, scrape-suck type gnathite pest, such as aphid, leafhopper, planthoppers, thrips, aleyrodids and resistant strain, also possess prevention and cure action to rice water weevil, acarid cochineal spider, hygiene pest and termite.

Description

Technical field [0001] The invention relates to nitromethylene derivatives, a preparation method and application thereof. technical background [0002] Nicotine (alkaloid of tobacco leaf extract) has long been used as a natural insecticide with a unique mechanism of action. Its target is the postsynaptic nicotinic acetylcholine receptors (nAChRs), but it is highly toxic to humans and kills Insect activity is low. In the mid-1980s, Bayer of Germany successfully developed the first neonicotinoid insecticide-imidacloprid. A series of nicotinic insecticides such as thiacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram and dinotefuran have been developed one after another. Due to their high insecticidal activity, broad insecticidal spectrum, low toxicity to mammals and aquatic animals, good system properties and appropriate field stability, neonicotinoid insecticides have become an important hot spot in the creation of pesticides. [0003] Compared with imidacloprid, nitrom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/02A01N43/90
Inventor 李忠钱旭红邵旭升徐晓勇田忠贞黄青春吴重言孙琴
Owner EAST CHINA UNIV OF SCI & TECH
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