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A kind of methyl guanidinourea derivative and its preparation method and application

A technology of methyl guanidinourea and its derivatives, which is applied in the field of pesticide compound preparation, and can solve the problems of difficult synthesis, high acquisition cost and large-scale application

Active Publication Date: 2022-05-06
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the chitinase inhibitors with ideal activity are mainly Argifin and Argadin, the natural products of cyclic pentapeptides, and Allosamidin, a pseudotrisaccharide. Difficult, high cost of acquisition and large-scale application, and so far no new pesticides targeting chitinase that can be applied to the control of agricultural pests and diseases have appeared on the market. In order to find a new small molecule chitin Massase inhibitors, the present invention uses the key active fragment methyl guanidinyl urea shared by the natural products Argifin and Argadin as the basic structure, designs and synthesizes a series of methyl guanidinyl urea derivatives, and tests their target enzyme inhibitory activity and Insecticidal activity

Method used

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  • A kind of methyl guanidinourea derivative and its preparation method and application
  • A kind of methyl guanidinourea derivative and its preparation method and application
  • A kind of methyl guanidinourea derivative and its preparation method and application

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Embodiment 1

[0042] Embodiment 1: the preparation of compound 2-(3-(methylcarbamoyl)guanidine)-N-(3-nitrophenyl)acetamide

[0043]

[0044] Take 0.02 mol of Boc-glycine formula III and 0.02 mol of CDI in a 100 ml single-necked flask and dissolve in 20 ml of tetrahydrofuran solution. After stirring at room temperature for 5 hours, add 0.02 mol of 3-nitroaniline compound formula II and heat at 60°C Stir under the conditions to continue the reaction for 24-30h. After the reaction, remove the solvent by rotary evaporation under reduced pressure, extract the reactant with ethyl acetate and water, collect the ethyl acetate phase, dry it with anhydrous sodium sulfate, and remove the ethyl acetate by rotary evaporation , recrystallized from methanol, and collected the solid product tert-butyl (2-(3-nitroaniline)-2-oxyethyl)carbamate by filtration, with a yield of 86%.

[0045]The structural confirmation data are as follows:

[0046] 1 H NMR (500MHz, CDCl 3 )δ9.07(s,1H),8.40(s,1H),7.91(dd,J=2...

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Abstract

The invention discloses a methyl guanidinourea derivative, a preparation method and application thereof. The structural formula of this type of compound is shown in Formula I. The compound has high-efficiency inhibitory activity on chitinases from the Asian corn borer and Serratia marcescens, and has application value in the prevention and control of agricultural pests such as the Asian corn borer, diamondback moth, and nematodes.

Description

technical field [0001] The invention relates to a class of methylguanidinourea compounds, a preparation method and application thereof, and belongs to the field of pesticide compound preparation. Background technique [0002] Chitin, also known as chitin, is a structural polysaccharide formed by the polymerization of N-acetylglucosamine through β-linkages. It is an important component of the shell of crustaceans, the outer skin of insects and the cell wall of fungi. Chitinases mostly belong to the glycosyl hydrolase family 18 (GH18), and chitinases from different species have a high degree of structural similarity, and these chitinases have N-acetylglucosamine linked by β-1,4- (GlcNAc) is hydrolyzed into chitin oligosaccharides. In insects, chitinase is the most abundant chitinase secreted protein in molting fluid or molting. Its main function is to hydrolyze and digest the old cuticle of insects after pupae; In bacteria, it provides a sugar source for the life activities o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/24C07C277/08C07C335/38C07C231/12C07C237/04C07C269/06C07C271/22C07D213/75A01N47/44A01P1/00A01P5/00A01P7/04
CPCC07C279/24C07C277/08C07C335/38C07C231/12C07C269/06C07D213/75A01N47/44C07C271/22C07C237/04
Inventor 张建军赵志祥
Owner CHINA AGRI UNIV