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Diphenyl ether ester compound and application thereof, and pesticide bactericide

An ester compound and compound technology, applied in the field of organic chemical drugs, can solve problems such as drug resistance and environmental pollution, and achieve the effects of strong bactericidal activity, high safety and strong inhibitory activity

Active Publication Date: 2021-11-23
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a green high-efficiency and low-toxic fungicide for the prevention and control of rice blast for the problems of drug resistance and environmental pollution in the existing rice blast fungicides

Method used

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  • Diphenyl ether ester compound and application thereof, and pesticide bactericide
  • Diphenyl ether ester compound and application thereof, and pesticide bactericide
  • Diphenyl ether ester compound and application thereof, and pesticide bactericide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Embodiment 1: the synthesis of compound II-1

[0070] The intermediate I used in this embodiment can be purchased directly, and the structure is as follows:

[0071]

[0072] Add intermediate I (5 mmol) to a 50 mL single-necked bottle, add 18 mL of dichloromethane, and slowly add (COCl) dropwise at room temperature 2 (8mmol), after the dropwise addition, the reaction was refluxed for about 1.5h, and the reaction progress was tracked by TLC, and the solvent was removed after the reaction. Add 20 mL of dry CH 2 Cl 2 , phenylpropanol (6 mmol), Et 3 N (10 mmol), reacted for about 0.5 h, followed by TLC until the acid chloride disappeared. After the reaction, wash once with 20 mL of water, wash twice with 10 mL of 1 mol / L HCl each time, wash with 10 mL of saturated NaHCO each time 3 Wash 2 times, recover the combined organic phase and wash with anhydrous Na 2 SO 4 After drying, petroleum ether ethyl acetate mixture was used as the eluent, separated and purified by ...

Embodiment 2

[0073] Embodiment 2: the synthesis of compound FY21001

[0074] The intermediate II-1 (5 mmol) prepared in Example 1, DMF (40 mL), potassium carbonate (10 mmol) and hydroquinone (10 mmol) were added into the flask, stirred and heated to 100°C. The reaction was monitored by TLC. After the reaction was completed, water (100ml) was added to the reaction system, ethyl acetate (30mL) was extracted three times, the organic layers were combined, and the organic phase was dried and concentrated for column chromatography to obtain compound FY21001, whose NMR spectrum was as follows :

[0075] 1 H NMR (500 MHz, DMSO- d 6 ) δ 9.47 (s, 1H), 7.90 – 7.84 (m, 2H), 7.27 –7.22 (m, 2H), 7.21 – 7.17 (m, 2H), 7.17 – 7.13 (m, 1H), 6.95 – 6.88 (m , 4H),6.81 – 6.76 (m, 2H), 4.18 (t,J = 6.5 Hz, 2H), 2.71 – 2.65 (m, 2H), 2.00 –1.91 (m, 2H).

Embodiment 3

[0076] Embodiment 3: the synthesis of compound FY21002

[0077] The intermediate II-1 (5 mmol) prepared in Example 1, DMF (40 mL), potassium carbonate (10 mmol) and o-cresol (10 mmol) were added into the flask, stirred and heated to 100°C. The reaction was monitored by TLC. After the reaction was completed, water (100ml) was added to the reaction system, ethyl acetate (30mL) was extracted three times, the organic layers were combined, and the organic phase was dried and concentrated for column chromatography to obtain compound FY21002.

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Abstract

The invention discloses a diphenyl ether ester compound and application thereof in preventing and treating rice blast caused by magnaporthe oryzae. The compound has a structural formula as shown in a formula (I) which is described in the specification. The compound shown in the formula (I) has very strong inhibitory activity and specificity on pathogenicity of magnaporthe oryzae, and has a great application value.

Description

technical field [0001] The invention belongs to the fields of organic chemical medicine and plant protection, and in particular relates to the use of a diphenyl ether ester compound as a fungicide, in particular to its application in preventing and treating rice blast caused by blast fungus. Background technique [0002] Rice is one of the most widely planted and most important food crops in the world, feeding more than half of the world's population. With the explosion of the global population, the demand and safety of rice production has become more and more important. Magnaporthe grisea ( Magnaporthe oryzae ) caused by rice blast is the most important destructive fungal disease that occurs widely in rice fields in my country and even in the world, and seriously threatens the safety of global food production. Rice blast causes 3 billion kilograms of grain loss in my country every year, and the annual output loss to the world can feed 60 million people. At present, the p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/76C07C67/08C07C67/31C07D213/65A01N37/10A01N43/40A01P3/00
CPCC07C69/76C07C67/08C07C67/31C07D213/65A01N37/10A01N43/40C07C69/92A01P3/00
Inventor 张正光何波刘木星郑小波
Owner NANJING AGRICULTURAL UNIVERSITY
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