1-(1,2-epoxy propyl)-n-nitroimidazolene amine-2, preparation and use thereof
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A technology of nitroimidazolidine and glycidyl ethylenediamine, applied to 1-(1,2-epoxypropyl)-N-nitroimidazolidine-2-ylamine and its preparation and application It can solve problems such as difficulty in governance and synthesis methods that have not yet been reported in the literature.
Inactive Publication Date: 2009-08-12
河北艾林化工科技有限公司
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In addition, because imidacloprid contains a large amount of pollutants in the production process of pyridine ring, it is difficult to control
[0003] As a new compound, 1-(1,2-epoxypropyl)-N-nitroimidazolidin-2-ylamine and its synthetic method have not been reported in the literature
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Embodiment 1
[0025] (1) synthesis of epoxypropyl ethylenediamine
[0026] Add 24g of ethylenediamine into a 250ml three-necked bottle, dissolve 37g of epichlorohydrin in 120ml of acetonitrile solvent, put it into a constant pressure titration funnel, add dropwise to the bottle while stirring, react at 45°C for 2.5h, cool, evaporate Go out acetonitrile and obtain epoxypropyl ethylenediamine;
[0027] (2) Synthesis of 1-(1,2-epoxypropyl)-N-nitroimidazolidin-2-ylamine
[0028] Dissolve 27.8g of epoxypropyl ethylenediamine and 15.6g of nitroguanidine in 200ml of water, slowly add 14.8g of concentrated hydrochloric acid (37%) dropwise under stirring, react at 85°C for 2.5h, cool with dichloro The crude product was obtained by extraction with methane and precipitation, and recrystallized with butanone to obtain 15.8 g of white crystals, yield 56.6%, m.p.98-99°C. 1 HNMR (CDCl 3 , 300MHz) δ: 2.561~3.667 (s, 4H, -N-CH 2 -CH 2 -N-), 3.680~4.095(s, 5H, -CH 2 -O-CH-CH 2 -), 8.146 (s, 1H, -NH); ...
Embodiment 2
[0030] Synthesis of 1-(1,2-epoxypropyl)-N-nitroimidazolidin-2-ylamine
[0031] Add 13.0g of N-nitroimidazolidine, 13.8g of potassium carbonate and 200ml of acetone solvent into the reaction flask, heat to 80°C, and after the N-nitroimidazolidine is basically dissolved, add 10.1g of epoxy chloride dropwise Propane, after heating, continue to react for 4h. After the reaction is completed, after the reactant is cooled, filter, evaporate the filtrate to dryness, add 50ml of water (can be properly heated to make it dissolve), extract with dichloromethane, and remove the solvent to obtain the crude product. The ketone was recrystallized to obtain 11.5 g of white crystals, with a yield of 61.8%.
[0032] Biological activity evaluation
[0033] 1. Determination of toxicity to aphids
[0034] spray method
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Abstract
The invention relates to 1-(1,2-epoxypropyl)-N-nitroimidazoline-2-amine which has a structural formula as shown in the picture. A preparation method of the compound comprises the steps of adding ethylenediamine to a reaction container, dropwise adding epoxy chloropropane in the reaction container while stirring, reacting for 2-3h, cooling, and vaporizing out acetonitrile to obtain epoxypropyl ethylenediamine; taking and dissolving nitroguanidine and the epoxypropyl ethylenediamine into water, dropwise adding hydrochloric acid solution while stirring, reacting for 2-3h, cooling, extracting, desolventizing to obtain crude product, and recrystallizating to obtain the product; or adding N-nitroimidazoline, potassium carbonate and organic solvent to the reaction container, heating to 75-81.6 DEG C, dropwise adding epoxy chloropropane in the reaction container after dissolving the N-nitroimidazoline, continuously heating until completing the reaction after dropwise adding, cooling reaction products, filtering, vaporizing filtrate to dry, adding water to residues, extracting by using methylene dichloride, desolventizing to obtain phase product, and recrystallizating by using butanone to obtain the product.
Description
technical field [0001] The present invention relates to 1-(1,2-epoxypropyl)-N-nitroimidazolidin-2-ylamine and its preparation method and application. Background technique [0002] As one of the best insecticides in the world today, imidacloprid has made great contributions to the control of piercing-sucking aphids, planthoppers and leafhoppers since it was put on the market in 1991. It can be said that there is currently no crop that does not use imidacloprid, especially the two major crops of rice and vegetables, which are used at least twice a season, effectively solving the long-standing problems of piercing-sucking aphids, planthoppers, and leafhoppers. prevention issues. Imidacloprid is a new type of nitroimine insecticide. Its insecticidal mechanism is mainly a nicotinic acetylcholine receptor agonist in the insect nervous system, thereby blocking the normal conduction of the insect central nervous system and causing the death of the pest. It is currently the most so...
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