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A kind of 1-trifluoromethyl cinnamyl alcohol derivative and its preparation method and application

A technology of trifluoromethyl and cinnamyl alcohol, applied in the field of pesticides, can solve the problems of less research on fungicides, and achieve the effects of broad-spectrum anti-phytopathogenic fungi and bacteria activity and good control effect

Active Publication Date: 2022-06-17
HAINAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few studies on fungicides with bidirectional conduction

Method used

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  • A kind of 1-trifluoromethyl cinnamyl alcohol derivative and its preparation method and application
  • A kind of 1-trifluoromethyl cinnamyl alcohol derivative and its preparation method and application
  • A kind of 1-trifluoromethyl cinnamyl alcohol derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] 1-Trifluoromethyl cinnamyl alcohol derivatives, whose structural formulas are shown in (I-1) to (I-4).

[0085] The preparation method of the 1-trifluoromethyl cinnamyl alcohol derivative comprises the following steps: under nitrogen conditions, 1 mmol of isopropyl titanate (Ti(O-i-Pr) 4 ) was slowly added to 1 mmol of 3-bromo-1,1,1-trifluoroacetone, 1 mmol of benzaldehyde derivative and 1 mmol of triphenylphosphine (Ph 3 P) in the mixture. After stirring the reaction at 80°C for 24 hours, the reaction product was obtained; the reaction product was treated with 5% HCl (10ml), and then extracted with ethyl acetate (3×20ml). After the extraction, the organic layer was washed with water (3×10ml). Add anhydrous sodium sulfate to dry, and evaporate the solvent to obtain a crude product; the crude product is separated and eluted by a chromatographic column to obtain the target compound; the eluent of the chromatographic column is petroleum ether and ethyl acetate at 20:1 Mi...

Embodiment 2

[0097] 1-Trifluoromethyl cinnamyl alcohol derivatives, whose structural formulas are shown in (I-5) to (I-12).

[0098] The preparation method of the 1-trifluoromethyl cinnamyl alcohol derivative includes the following steps: adding 1 mmol of 1-trifluoromethyl cinnamaldehyde derivative and 1.2 mmol of Grignard reagent to 5 mL of tetrahydrofuran (THF) at room temperature , stirred, heated to 66°C under reflux for 2 h, then the reaction was cooled to room temperature, added to 2M HCl (15 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with water (3 x 10 ml), dried over anhydrous sodium sulfate, and the solvent was removed in vacuo to give the crude product. The crude product is separated and eluted by a chromatographic column to obtain the product; the eluent of the chromatographic column is obtained by mixing petroleum ether and ethyl acetate in a volume ratio of 20:1.

[0099] The reaction formula of this reaction is as follows:

[0...

Embodiment 3

[0119] A 1-trifluoromethyl cinnamyl alcohol derivative, the structure of which is shown in (I-13):

[0120] The preparation method of the 1-trifluoromethyl cinnamyl alcohol derivative includes the following steps: dissolving 1 mmol of 1-trifluoromethyl cinnamaldehyde derivative and 1.2 mmol of trifluoromethyl trimethyl silane in ethylene glycol in methyl ether (5 mL). 0.02 mmol of cesium fluoride was added at 0 °C, and the reaction was carried out at room temperature for 4 h. Then, 1.2 mmol of tetrabutylammonium fluoride and 5M HCl (5 mL) were added, and the reaction was continued for 2 h at room temperature to obtain the reaction product. The reaction product was treated with water (10 mL) and extracted with ethyl acetate (3 x 20 mL). The organic layer was washed with water (3×10 mL), dried and evaporated to remove the solvent to obtain a crude product; the crude product was separated and eluted by a chromatographic column to obtain the target compound; the eluents of the c...

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Abstract

The invention provides a 1-trifluoromethyl cinnamyl alcohol derivative and its preparation method and application. The 1-trifluoromethyl cinnamyl alcohol derivative of the present invention has excellent broad-spectrum antifungal activity against plant pathogenic bacteria in agricultural production , at the same time, it also has a good control effect on bacterial diseases, and there is no cross-resistance with commercial fungicides; among them, 1-trifluoromethyl cinnamyl alcohol derivatives are effective against cowpea powdery mildew, Wheat stripe rust, corn rust, and rubber powdery mildew have achieved more than 90% control effect; 1-trifluoromethyl cinnamyl alcohol derivatives can effectively control rice bacterial blight in pot experiments, and the commercial fungicide Zhongshengmycin quite active. In addition, the 1-trifluoromethylcinnamyl alcohol derivative of the present invention has the ability of two-way conduction in plants. In actual production and application, it can prevent above-ground diseases through seed treatment or root application, and can also be applied through foliage. Prevent root diseases.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a 1-trifluoromethyl cinnamyl alcohol derivative and a preparation method and application thereof. Background technique [0002] Plant pathogenic fungi infect crops and grains, seriously threatening their yield, and the application of fungicides has effectively controlled the occurrence and prevalence of plant pathogenic fungi. However, plant resistance and environmental problems are easily caused by the abuse of fungicides, so it is necessary to develop an excellent fungicide with high antifungal activity, good systemic conductivity and low resistance. Among them, the systemic conductivity of fungicides determines whether the fungicides can be quickly absorbed by plants and transmitted to various tissues. Good systemic conductivity is the key to the antifungal effect of fungicides in plants. However, there are few studies on fungicides with bidirectional conduction. [0003]...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/48C07C29/38C07C29/40A01N31/04A01P3/00A01P1/00
CPCC07C33/483A01N31/04
Inventor 孙然锋张萌胡展窦孟兰谢佳
Owner HAINAN UNIV
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