Monoterpene phenolic derivative, synthetic method of monoterpene phenolic derivative and application of monoterpene phenolic derivative in pesticides

A synthesis method and monoterpene phenol technology are applied in the field of pesticides and achieve the effects of good bactericidal effect, simple structure and easy synthesis.

Active Publication Date: 2019-06-28
YUNNAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no report of this monoterpene phenolic compound as an agricultural fungicide

Method used

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  • Monoterpene phenolic derivative, synthetic method of monoterpene phenolic derivative and application of monoterpene phenolic derivative in pesticides
  • Monoterpene phenolic derivative, synthetic method of monoterpene phenolic derivative and application of monoterpene phenolic derivative in pesticides
  • Monoterpene phenolic derivative, synthetic method of monoterpene phenolic derivative and application of monoterpene phenolic derivative in pesticides

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preparation example Construction

[0033] Its synthetic steps of the synthetic method of monoterpene phenol compound of the present invention are as follows:

[0034]

[0035] The application of the monoterpene phenolic compound of the present invention in pesticides is used to inhibit or kill phytopathogenic fungi, and the phytopathogenic fungi that are inhibited or killed are tomato early blight, tomato cinerea, cucumber fusarium wilt, and rice blast fungus or rice sheath blight.

Embodiment 1

[0036] Embodiment 1: monoterpene phenolic compound (C 12 h 15 ClO 2 )Synthesis.

[0037] The concrete steps of the synthetic method of this monoterpene phenol compound are as follows:

[0038] (1) Synthesis of intermediate 5-methyl-2-isopropyl-4-chlorophenol

[0039] 1.5 g of thymol was dissolved in 20 mL of dichloromethane, and the resulting solution was cooled to 0°C. A solution of 1.6 g of sulfonyl chloride in dichloromethane (5 mL) was slowly added within 20 min using a constant pressure dropping funnel, and the resulting mixture was continued to react at room temperature after the addition was complete. TLC monitors the progress of the reaction. After the reaction is completed, add 30 mL of distilled water, extract three times with 30 mL of ethyl acetate, combine the organic phases, dry and concentrate, and use eluent (petroleum ether: ethyl acetate=50:1) column chromatography to obtain the compound 5-Methyl-2-isopropyl-4-chlorophenol, yield 78%, pale yellow oil. ...

Embodiment 2

[0050] Embodiment 2: monoterpene phenolic compound (C 12 h 15 BrO 2 )Synthesis.

[0051] The concrete steps of the synthetic method of this monoterpene phenol compound are as follows:

[0052] (1) Synthesis of intermediate 5-methyl-2-isopropyl-4-bromophenol

[0053] 1.218 g of thymol was dissolved in 20 mL of acetic acid, and the resulting solution was cooled to 0°C. Add 0.51 mL of Br slowly within 20 min using a constant pressure dropping funnel 2 , After the dropwise addition was completed, the resulting mixture was stirred at room temperature for 6 h. The reaction was poured into 50 mL of ice water, extracted three times with 30 mL of dichloromethane, the organic phases were combined, dried and concentrated, and the intermediate 5-methanol was obtained by column chromatography with eluent (petroleum ether: ethyl acetate=40:1). 2-isopropyl-4-bromophenol, yield 82%, pale yellow oil.

[0054] (2) Synthesis of the target compound

[0055] Take 229mg of the intermediat...

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PUM

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Abstract

The invention relates to a monoterpene phenolic derivative, a synthetic method of the monoterpene phenolic derivative and application of the monoterpene phenolic derivative in pesticides, in particular to application of the monoterpene phenolic derivative in the aspect of fungicide pesticides, and belongs to the technical field of pesticides. The technical aims of a new monoterpene phenolic derivative, a synthetic method of the new monoterpene phenolic derivative and application of the new monoterpene phenolic derivative in pesticides are achieved, and the structure of the compound is shown inthe formula I. The compound is simple in structure, novel, easy to synthesize, also has the fungicidal activity, and has a good bacteriostatic or sterilizing effect on important plant pathogenic fungi such as alternaria solani, botrytis cinerea, cucumber fusarium wilt, magaporthe grisea and rice sheath blight fungi.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a monoterpene phenol derivative, a synthesis method thereof and an application in pesticides. Background technique [0002] At present, the commonly used prior art in the industry is as follows: plant disease is one of the main factors affecting agricultural production, and the prevention and treatment of plant disease in various countries in the world mainly uses chemical agents. The resistance of plant pathogens to fungicides is one of the main problems in the chemical control of plant diseases. Under the long-term selection of single agents, the resistance of plant pathogens is becoming more and more serious and common. Therefore, new low-resistance agents are constantly being developed. Species are a challenge in pesticide research. [0003] Monoterpene phenolic derivatives represented by carvacrol and thymol widely exist in plants, and are one of the main com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/63C07C67/14C07C253/30C07C255/55A01N37/40A01N37/02A01P3/00
Inventor 苏发武叶敏王凯博范黎明查友贵
Owner YUNNAN AGRICULTURAL UNIVERSITY
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