Furan glucosyl triazole type compound and preparation method and bactericide thereof
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A glucofuranose and triazole-based technology, which is applied in the preparation of sugar derivatives, botanical equipment and methods, fungicides, etc., to achieve good antibacterial activity and remarkable antibacterial effect
Active Publication Date: 2018-03-30
BEIJING UNIV OF AGRI
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However, the existing agricultural insecticides and fungicides targeting the enzymes of the chitin biosynthesis pathway mainly act on chitin synthase or chitinase, and there is no primary and key agent in chitin biosynthesis at home and abroad. Research reports on agricultural fungicidal compounds targeting glucosamine-6-phosphate synthase, only preliminary research in medicine
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Embodiment 1
[0051] Glucofuranosyl triazole compounds, with target (R 1 = Me,R 2 =C 6 h 4 The synthesis of -) is an example, and the preparation method is as follows:
[0052] 1. Synthesis of Compound 2
[0053] Add 20 g of diacetone glucose into a 500 mL round bottom flask, dissolve in anhydrous DMF, slowly add 3.7 g of NaH at room temperature, react for a while, then slowly add 12 mL of methyl iodide dropwise, and react for 6 h at room temperature, TLC [V (petroleum ether): V (ethyl acetate) = 4:1] detection + complete reaction, use diatomaceous earth to filter to remove insoluble matter, dissolve with dichloromethane after concentration under reduced pressure, wash with water, separate liquid, dry, and obtain white powdery solid after concentration The target product compound 2. Yield 98%.
[0054] 2. Synthesis of compound 3
[0055] Add 15g of compound 2 and 50mL of 60% acetic acid into a 500mL round bottom flask, stir at room temperature for 10h, TLC [V (petroleum ether): V (et...
Embodiment 2
[0065] R 1 is methyl, R 2 4-Cl-C 6 h 4 -or 4-F-C 6 h 4 -;
[0066] Other steps are the same as in Example 1, except that in the synthesis method of compound 7, phenylacetylene is replaced by 4-Cl-phenylacetylene or 4-F-phenylacetylene.
Embodiment 3
[0068] R 1 is methyl, R 2 4-NO 2 -C 6 h 4 -;
[0069] Other steps are the same as in Example 1, except that in the synthetic method of compound 7, phenylacetylene is replaced by 4-NO 2 - Phenylacetylene.
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Abstract
The invention relates to the field of bactericidal compounds, in particular to a furan glucosyl triazole type compound and a preparation and a bactericide thereof. The molecular formula of the furan glucosyl triazole type compound is shown in the following description, wherein R1 is methyl or benzyl, and R2 are phenyl and derivative of the phenyl or ethyl derivatives. Based on structural characteristics of the substrate fructose-6-phosphate and an ISOM catalytic hypothesis mechanism, the inventor adopts a five-membered furan glucose derivative with a similar structure as a basic skeleton, introduces an effective active group triazole structure of pesticides, designs a series of novel furan glucosyl triazole type compounds for the first time, studies the biological activities of the furan glucosyl triazole type compound, examines structure-activity relationships of the furan glucosyl triazole type compound, and lays the foundation for selecting better inhibitors.
Description
technical field [0001] The invention relates to the field of bactericidal compounds, in particular to a glucofuranosyl triazole compound, a preparation method thereof and a bactericide. Background technique [0002] Agriculture is the foundation of the national economy, a top priority concerning national security, and a long-term challenge and strategic issue facing economic security and social stability. As an indispensable material for agricultural production, pesticides play a key role in resisting pests and diseases. As the country that ranks first in the world in terms of pesticide usage and output, with the entry into the WTO, we can no longer imitate existing foreign varieties. my country's pesticide industry is facing huge challenges. How to develop new pesticides with independent intellectual property rights is a current priority. The most important. [0003] The discovery of lead compounds is the first and crucial step in the development of new pesticides. Only w...
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