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The New Technology of Pymetrozine and Study on the Synthesis and Biological Activity of New Triazone Compounds

Author: LiHongXin
Tutor: XuLiangZhong
School: Qingdao University of Science and Technology
Course: Physical and chemical
Keywords: pymetrozine synthesis triazone biological activity
CLC: TQ453.2
Type: Master's thesis
Year: 2011
Downloads: 164
Quote: 1
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Abstract


The broad spectrum acaricides, Pymetrozine, discovered at Ciba-Geigy Corporation during the 1988, were feature of high efficiency, low toxicity, environmentally friendly and unique mode of action has caused widespread concern. Base on the literature researched, the study on the new technology of Pymetrozine and 25 novel triazone compounds were synthesized in detail through two part in this article.The synthesis of the intermediate 5-methyl-3-(2-oxopropyl)-1,3,4-oxadiazol-2 -one and nicotinaldehyde were two crucial steps in the synthesis of pymetrozine. Ethyl acetate was used as initial material then was carried out hydrazine hydrate, phosgene, bromoacetone respectively for synthesis of the intermediate 5-methyl-3-(2-oxopropyl)-1,3,4-oxadiazol-2-one. 3-Chloromethylpyridine was used as initial material for synthesis of the intermediate nicotinaldehyde. Lastly, the intermediate 5-methyl-3-(2-oxopropyl)-1,3,4-oxadiazol-2-one carried out hydrazine hydrate and deaminative hydrolysis for amidetriazinone. The amidetriazinone and intermediate nicotinaldehyde were reacted for pymetrozine with the yiled of 63.3%( base on the ethyl acetate). The factor that may affect each step is anatomized and each reaction conditions are optimized. One-pot synthesis reaction was established for the intermediate 5-methyl-3-(2-oxopropyl)-1,3,4-oxadiazol-2-one. Moreover, a new synthetic method was established for the intermediate nicotinaldehyde, which lead to reduced cost and requirement to the equipment compare to the present literature.The second part mainly discussed the preparation triazone compounds in two series. The structures are listed as follows: Twenty-five new triazone compounds containing amidetriazinone were designed and synthesized with the isosteric principl. Their structures were confirmed with IR, ~1H NMR and EA. The structure of several compounds were determined by X-ray determination. Spectral properties and biological activities were also analyzed. The results of biological test show that several compounds possess good activity and have high potential value as novel pesticide.

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