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Synthesis of compound containing aryl ether triazole

A technology of bactericidal activity and compounds, applied in the directions of fungicides, biocides, organic chemistry, etc., can solve the problems of inhibition of strawberry growth, single action mechanism and action site, loss of high efficiency, etc., and achieve significant specific killing activity. Effect

Inactive Publication Date: 2008-07-23
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But on the other hand, triazole fungicides are systemic fungicides with a single action mechanism and action site. After long-term and frequent use, the disease has developed serious drug resistance, and many varieties have lost their original properties due to resistance problems. Some efficiency
For example, triadimefon is used to control strawberry powdery mildew, and the control effect is low if the dosage is small. If the dosage is large, it will easily cause phytotoxicity and inhibit the growth of strawberries.

Method used

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  • Synthesis of compound containing aryl ether triazole
  • Synthesis of compound containing aryl ether triazole
  • Synthesis of compound containing aryl ether triazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 2-(2-chloro-4-(4-chlorophenoxy)phenyl)-2-styryl propylene oxide

[0018] Take 3.68g (0.01mol) of 1-(2-chloro-4-(4-chlorophenoxy)phenyl)-3-phenylprop-2-en-1-alcohol, 2.26g ( 0.012mol) and 40 mL of diethyl ether were put into a 100 mL three-necked flask, and 2.69 g of potassium hydroxide powder was added under cooling and stirring in an ice bath, and then refluxed and stirred for 6 hours, and the reaction solution was neutralized to PH=7 with 30% dilute sulfuric acid, diethyl ether Extracted, dried and evaporated to obtain 3.59 g of light yellow solid 2-(2-chloro-4-(4-chlorophenoxy)phenyl)-2-styryl propylene oxide, yield 94.1%, melting point: 79 ~82°C.

Embodiment 2

[0019] Example 2: 2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-phenyl-1-(1H-1,2,4-triazol-1-ylmethyl) - Preparation of but-3-en-2-ol

[0020] Add 3.82g (0.01mol) of 2-(2-chloro-4-(4-chlorophenoxy)phenyl)-2-styryl propylene oxide, 0.8g (0.012mol) of triazole into a 50mL single-necked flask ), catalyst A and N,N-dimethylformamide 20mL, reflux reaction for 6h, the reaction solution was poured into water, the solvent was extracted, subtracted and evaporated to obtain a yellow viscous liquid, and recrystallized with acetone to obtain a yellow solid 2-(2- Chloro-4-(4-chlorophenoxy)phenyl)-4-phenyl-1-(1H-1,2,4-triazol-1-ylmethyl)-but-3-ene-2- Alcohol, 3.52g, yield 78.0%, melting point 142-145°C.

[0021] Other target compounds (I) can be prepared by a method similar to the above. Listed in Table 1 are some compounds synthesized by the present invention.

[0022]

[0023]

[0024] The aryl ether triazole compounds synthesized by the present invention have very slight specific in...

Embodiment 3

[0025] Embodiment 3 antibacterial activity test

[0026] (1) Experimental method: using the isolated plate method

[0027] 1. Materials and methods

[0028] (1) Test strain

[0029] In this experiment, the following common agricultural plant fungal diseases were selected: wheat head blight (G.Zease), tomato early blight (A.Solani), asparagus stem blight (R.Solani), apple ring spot (P.Pircola), peanut Brown spot (C. Arachidicata).

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Abstract

The invention relates to a synthesis and fungicidal activity of an aryl ether based triazole compound which comprises a structural formula I, the general expression is shown in the figure, in which R represents a hydrogen atom, an alkyl, a methoxyl, a nitro or a halogen. The synthesis and fungicidal activity of an aryl ether based triazole compound has the advantages of strong specificity inhibitory activity to peanut brown spot pathogen at 50ppm to 200ppm and ability to be used for preparing agricultural fungicides.

Description

technical field [0001] The invention belongs to an agricultural fungicide, and relates to an aryl ether-based triazole compound and its preparation method and application. The compound provided by the invention has high biological activity against peanut brown spot fungus. Background technique [0002] The harmful organisms that harm animals and plants and make them disease are mainly fungi, bacteria and viruses. For plants, the main diseases of plants are fungal diseases. The vast majority of commercialized bactericidal and disease-preventing agents are fungicides, only a handful of bactericides, and very few antiviral agents. One of the factors is that fungal diseases are widespread, causing the greatest damage and loss. Among the numerous fungal disease control agents, triazole fungicides are typical types of fungicides. In the past 30 years, triazole fungicides have been favored for their high efficiency, low toxicity, and broad spectrum. Not only that, most triazole ...

Claims

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Application Information

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IPC IPC(8): C07D249/08A01N43/653A01P3/00
Inventor 建方方许良忠胡志强朱琪于观平
Owner QINGDAO UNIV OF SCI & TECH
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