Diphenyl ether structure-containing pyrazolecarboxamide compound and its preparation method and use

A technology of pyrazole amide and diphenyl ether, applied in the field of pyrazole amide compounds, can solve the problems of no control effect and zero control effect on cucumber powdery mildew

Active Publication Date: 2017-01-18
ZHEJIANG RES INST OF CHEM IND CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] From the data disclosed in the examples of the description, it can be known that compounds CN-1 and CN-2 have a certain control effect on rice sheath blight, but have almost no control effect on cucumber powdery mildew, and compound CN-2 has the best control effect on cucumber powdery mildew It is more than 66.67% (dosage is more than 12.5mg / L), but when the dosage drops below 12.5mg / L, the control effect on cucumber powdery mildew is 0

Method used

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  • Diphenyl ether structure-containing pyrazolecarboxamide compound and its preparation method and use
  • Diphenyl ether structure-containing pyrazolecarboxamide compound and its preparation method and use
  • Diphenyl ether structure-containing pyrazolecarboxamide compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1: compound 1 is synthesized

[0084]

[0085] Step (1): Synthesis of 1-methyl-3-difluoromethyl-5-hydroxy-1H-pyrazole

[0086] In a 500ml three-neck flask, add 42 grams of ethyl difluoroacetoacetate in 300ml of toluene, add 10 grams of acetic acid, cool, add 1.1 times the molar amount of 40% methylhydrazine aqueous solution under stirring, and drop it for about 1 hour. , the reaction system was raised to room temperature, and reacted overnight. The next day, 100ml of water was added to the system, the toluene layer was separated, the organic layer was dried with anhydrous magnesium sulfate, and the toluene was distilled off under reduced pressure to obtain 32 grams of a light red solid. The light red solid is 1-methyl-3-difluoromethyl-5-hydroxy-1H-pyrazole, with a melting point of 130-132°C, and it is used in the next reaction without purification.

[0087] Step (2): Synthesis of 1-methyl-3-difluoromethyl-5-chloro-4-formaldehyde-1H-pyrazole

[0088] Add ...

Embodiment 2

[0100] Embodiment 2: compound 2 is synthesized

[0101]

[0102] Step (1): 2-bromo-4-trifluoromethyl-phenol synthesis

[0103] Dissolve 32 g of p-trifluoromethylphenol in 200 ml of dichloromethane, add equimolar liquid bromine dropwise under cooling, and the dropwise addition is completed in about 2 hours, then stir at room temperature for 12 hours, and wash the system with saturated sodium bicarbonate until it becomes neutral. After drying, the solvent was distilled off to obtain 40 g of viscous liquid. The obtained viscous liquid is 2-bromo-4-trifluoromethyl-phenol, and its NMR data is: 1 HNMR (600MHZ, CDCl3 / TMS) δ = 7.75 (1H, s), 7.47 ~ 7.49 (1H, d), 7.08 ~ 7.10 (1H, d), 6.21 (1H, s) ppm, used for the next reaction without purification .

[0104] Step (2): Synthesis of 2-bromo-1-(2-nitro-phenoxy)-4-trifluoromethylbenzene

[0105] Add 14.1 grams (0.1mol) of 2-fluoronitrobenzene into a 150ml single-necked bottle, add 70ml N, N-dimethylformamide, add 1.5 times the molar...

Embodiment 3

[0111] Embodiment 3: compound 4 is synthesized

[0112]

[0113] Step (1): Synthesis of 2-chloro-1-(2-nitro-5-fluoro-phenoxy)-4-trifluoromethylbenzene

[0114] Add 15.9 grams (0.1mol) of 2,4-difluoronitrobenzene into a 150ml single-necked bottle, add 150ml N,N-dimethylformamide, add 1.5 times the molar amount of potassium carbonate, and cool the system to 10°C. Then slowly add 19.6 grams (0.1mol) of 2-chloro-4-trifluoromethylphenol for about 1 hour, keep the temperature and react for 2 hours, then pour the system into 500 ℃ of water, extract with ethyl acetate, and dry with anhydrous magnesium sulfate , evaporated the solvent, and purified by column chromatography to obtain 10 g of the product. The product is 2-chloro-1-(2-nitro-5-fluoro-phenoxy)-4-trifluoromethylbenzene with a melting point of 118-120°C and the NMR data are as follows:

[0115] 1 HNMR (600MHZ, CDCl3 / TMS): δ=8.13~8.16(1H,q), 7.80(1H,s), 7.56~7.58(1H,d), 7.14~7.15(1H,d), 6.99~7.02(1H ,m), 6.62~6.64(1H,q)...

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Abstract

The invention discloses a diphenyl ether structure-containing pyrazolecarboxamide compound. A general structural formula and substituent groups are defined in the specification. The diphenyl ether structure-containing pyrazolecarboxamide compound is suitable for agricultural sterilization and is especially suitable for prevention of sheath blight, damping-off, powdery mildew or rust diseases.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides and relates to a class of pyrazole amide compounds containing a diphenyl ether structure. Background technique [0002] Rice and wheat are the main food crops in the world, but due to diseases such as sheath blight, their yields decrease every year. Powdery mildew is also commonly found in various crops, seriously affecting the growth of crops. Due to the long-term use of pesticides in agriculture, the diseases on crops have developed resistance to them, which significantly reduces the control effect of existing pesticides. For example, crops have developed resistance to pesticides used to control sheath blight and powdery mildew. In order to improve the control effect, the use of pesticides must be increased, which has caused serious harm to the environment. Therefore, it is necessary to continuously discover new varieties of pesticides with new mechanisms of action. [0003] In recent y...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/16A01N43/56A01P3/00
CPCA01N43/56C07D231/16
Inventor 许天明胡伟群孔小林张蕊蕊郑志文朱卫刚陈杰黄红英袁静
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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