氟吡菌酰胺的合成工藝研究
發(fā)布時(shí)間:2018-04-27 04:34
本文選題:殺菌劑 + 氟吡菌酰胺; 參考:《河北科技大學(xué)》2017年碩士論文
【摘要】:農(nóng)藥在現(xiàn)代農(nóng)業(yè)生產(chǎn)里占有舉足輕重的地位。其中,吡啶基乙基苯甲酰胺類農(nóng)藥更是成為近幾年來(lái)大家研究的熱點(diǎn)。該類殺菌劑具有新奇的結(jié)構(gòu),與眾不同的作用機(jī)制,還有廣譜、療效高、毒性低、殘留少、活性高、環(huán)境友好等好處,具有很大的發(fā)展空間。拜耳作物科學(xué)公司開發(fā)出一種全新的吡啶基乙基苯甲酰胺類的殺菌劑:氟吡菌酰胺,其原藥2010年在美國(guó)首次登記,可用于防治70多種作物的多種病害,無(wú)論單用或混用均表現(xiàn)出較高活性。氟吡菌酰胺是一個(gè)極具潛力的殺菌劑品種,隨著科技的不斷推進(jìn),該產(chǎn)品在未來(lái)會(huì)有更大的市場(chǎng)應(yīng)用價(jià)值。本文主要研究氟吡菌酰胺的合成工藝優(yōu)化。本課題對(duì)氟吡菌酰胺及其關(guān)鍵中間體鄰三氟甲基苯甲酰氯的合成路線進(jìn)行了詳細(xì)的闡述和優(yōu)劣比較,從中篩選出合成目標(biāo)產(chǎn)物的最佳工藝。最終確定了以2,3-二氯-5-三氟甲基吡啶和氰乙酸甲酯作為起始原料,經(jīng)過(guò)親核取代、去烷氧羰基化、氰基還原、再與中間體鄰三氟甲基苯甲酰氯酰胺化反應(yīng)制得目標(biāo)產(chǎn)物,總收率為51.4%,含量≥95.8%。其中,中間體的合成是以鄰三氟甲基氯苯作為起始原料,經(jīng)過(guò)格氏化反應(yīng)、成酸、酰氯化反應(yīng)最終合成鄰三氟甲基苯甲酰氯。該工藝具有合成步驟短,操作簡(jiǎn)單、高收率高純度的特點(diǎn),適合工業(yè)化生產(chǎn)。氟吡菌酰胺及其部分中間體的化學(xué)結(jié)構(gòu)經(jīng)核磁共振氫譜確證。
[Abstract]:Pesticides play an important role in modern agricultural production. Among them, pyridyl ethyl benzoyl amine pesticides have become the focus of research in recent years. These fungicides have novel structure, distinctive mechanism, broad spectrum, high curative effect, low toxicity, low residue, high activity and environmental friendliness. Bayer crop Science has developed a new pyridyl ethyl benzoamide fungicide, flumiramide, which was first registered in the United States in 2010 and can be used to control multiple diseases in more than 70 crops. Both single and mixed use showed high activity. Flumiramide is a potential bactericide variety, with the development of science and technology, the product will have greater market value in the future. In this paper, the synthesis process optimization of flumiramide was studied. In this paper, the synthetic route of flumiramide and its key intermediate, o-trifluoromethyl benzoyl chloride, was described and compared in detail. Finally, the target product was prepared by the reaction of 2-trichloro-5-trifluoromethyl pyridine and methyl cyanoacetate as starting materials through nucleophilic substitution, decarbonylation, reduction of cyanide, and reaction with the intermediate o-trifluoromethyl benzoyl chloride amide. The total yield was 51.4 and the content was 鈮,
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