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Studies on Synthesis and Properties of Spiro-heterocyclic Compounds with Biological Activities

Author: ZhuXiaoXing
Tutor: XuGuangYu;LiuAiPing
School: Hunan Normal University
Course: Organic Chemistry
Keywords: Organic Synthesis Biological activity Spiroheterocyclic
CLC: TQ450.41
Type: Master's thesis
Year: 2010
Downloads: 104
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Pesticides in the 21st century must have efficient, safe, economic, environment-friendly features. Heterocyclic compounds with broad-spectrum, high efficiency active characteristics, in recent years, it has become the mainstream of the pesticide discovery, more than 90% of the world's pesticides patents on heterocyclic compounds. Spiro heterocyclic compounds is an important branch of heterocyclic compounds, have occupied an important position in today pesticide and pharmaceutical research and development. In this paper, containing a spiro structure pesticide research progress and spiro quarter acids to the pesticide on the latest research and development progress in a spiro quarter acids of the bioactive compounds for the pilot, the sub-structure connection method \The synthesis of the objective compound according to the structure can be divided into the following two categories: (1) 3 - (2 - methylphenyl) -2 - oxo-1 - oxaspiro [4,5] - dec-3 - em-4 - 13 alcohol derivative (I a to I m): (2) 3 - (2 - methylphenyl) -2 - oxygen-dioxo-1 - oxaspiro [4,4] - non-3 - ene -4 - of alcohol derivatives II (Ⅰ a ~ Ⅰ n): the synthesis conditions of the various intermediates and target compounds more detailed discussion of all target compounds were purified and characterized by IR, 1H NMR, LC / MS structure characterization. Pesticide bioassay standard operating procedures for testing the biological activity of the synthesized compounds. The compound I and compound II are compounds Ⅰ a test concentration of 1000 mg / L Ⅰ and d, Ⅰ e Ⅰ m armyworm lethal activity are 100% to higher than Spirodiclofen lethal activity showed varying degrees of insecticidal activity: , compound Ⅰ f the lethal activity to 95%, and Spirodiclofen ester lethal activity fairly; test concentration of 500 mg / L compound Ⅰ b, Ⅰ g, Ⅰ l on aphids lethal activity, respectively, to 97.5%, 97.22%, 98.99%, than Spirodiclofen lethal activity slightly higher; under test concentration of 500 mg / L, the compound Ⅰ d Ⅰ g Ⅰ m of red spider's lethal activity for 97.06%, 92.37%, 97.16%, higher than the Spirodiclofen lethal activity; overall to said target compound I have relatively high insecticidal activity. Compound II armyworms, aphids and spider mites showed insecticidal activity, lethal activity of compounds Ⅱ a, Ⅱ j armyworm test concentration of 1000 mg / L, are 100% higher than the lethal activity of Spirodiclofen compounds Ⅱ e Ⅱ l the lethal activity of 95%, 95.45%, and Spirodiclofen ester lethal activity fairly; under test concentration of 500 mg / L, the compound Ⅱ b, Ⅱ e Ⅱ l on aphids lethal activity of 100%, Ⅱ a Ⅱ c Ⅱ i on aphids lethal activity were 98.57%, 99.44%, 97.46%, than Spirodiclofen lethal activity to be high; under test concentration of 500 mg / L, the compound Ⅱ d Ⅱ g of red spider's lethal activity 89.02 %, 88.56%, than Spirodiclofen lethal activity slightly higher; Generally speaking, the target compound II is also a relatively high insecticidal activity.

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