Pyrazole compound, salt and uses thereof,

Abstract

The invention discloses a pyrazole compound and a salt thereof, wherein the structural formula of the pyrazole compound is represented by a formula (I). According to the invention, the pyrazole compound has good prevention and control effect on various gramineous weeds and broadleaf weeds in agriculture or other fields, can achieve good prevention and control effect at a low concentration, has wide weed control spectrum, can kill weeds in crops by using only one herbicide, and is safe and reliable; and the pyrazole compound provided by the invention has the advantages of low toxicity, less residue in crops and small harm to human and livestock, well solves the problems of high toxicity and more residue in crops in the existing herbicides, and enhances the safety of agricultural production.

Description

technical field

[0001] The invention relates to the technical field of herbicides, in particular to a pyrazole compound and its salt and use. Background technique

[0002] Weeds in farmland are the enemy of crops. Weeds have strong reproductive ability and compete with crops for sunlight, water and fertilizer. According to statistics, crops in the world lose an average of 12% of their output every year due to weed damage. Therefore, the control of weeds is the most important An important part of efficient farming. The use of chemical agents to weed control is the most effective and labor-saving method among many weed control methods. Although there are various types of herbicides on the market, due to the continuous expansion of the market, the resistance of weeds and the service life of drugs, and people's increasing attention to the environment, people still need to continuously develop new high-efficiency, safe and economical herbicides New varieties. Therefore, new he...

Examples

Embodiment 1

[0245] 4-(2-Chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-dimethyl-1H- Preparation of pyrazol-5-ylquinoline-8 carboxylate (compound 1)

[0246]

[0247] The first step reaction: the preparation of 1,3-dimethyl-1 hydrogen-pyrazol-5-ol: add methyl acetoacetate (13.0g, 0.1mol) dropwise to methanol (70ml) solution at room temperature A solution of hydrazine (4.66 g, 0.101 mol) in methanol (6 ml) was added dropwise for 20 minutes, during which the temperature of the solution rose to 45°C. The reaction solution was heated to reflux, dehydrated by a dehydrator, and reacted at reflux for 2 hours, monitored by a TLC plate, and a small amount of raw materials remained. An appropriate amount of solvent was removed under reduced pressure, ethyl acetate / petroleum ether (1:2) was added to make a slurry, and filtered to obtain 10.6 g of a red solid product, yield: 93%. LC-MS [M+H]+=113.07, [M+Na]+=135.05, [M+K]+=151.02.

[0248] The second step reaction: the p...

Embodiment 2

[0256] 4-(2-Chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-dimethyl-1H- Preparation of pyrazol-5-yl 3,7-dichloroquinoline-8-carboxylate (compound 9)

[0257]

[0258] The first step reaction: the preparation of 3,7-dichloroquinoline-8-acyl chloride: at room temperature, 3,7-dichloroquinoline-8-carboxylic acid (2.85g, 0.01mol), dichloroethane (60ml) and N, N-dimethylformamide (0.1 g) were added into a three-necked flask, and thionyl chloride (2.38 g, 0.02 mol) was added dropwise to the above mixture. Heat to reflux for 5 hours. Heating was stopped, and the solvent and residual thionyl chloride were removed under reduced pressure to obtain 2.2 g of the product with a yield of 86%.

[0259] The second step reaction: 4-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-di Preparation of methyl-1H-pyrazol-5-yl 3,7-dichloroquinoline-8-carboxylate: at room temperature, (2-chloro-4-(methylsulfonyl)-3-((2 ,2,2-trifluoroethoxy)meth...

Embodiment 3

[0261] 4-(2-Chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-dimethyl-1H- Preparation of pyrazol-5-yl 7-chloro-3-methylquinoline-8-carboxylate (compound 10)

[0262]

[0263] The first step reaction: the preparation of 7-chloro-3-methylquinoline-8-acid chloride: at room temperature, 7-chloro-3-methylquinoline-8-carboxylic acid (2.33g, 0.01mol), di Ethyl chloride (60ml) and N,N-dimethylformamide (0.1g) were added into a three-necked flask, and thionyl chloride (2.38g, 0.02mol) was added dropwise to the above mixture. Heat to reflux for 5 hours. Heating was stopped, and the solvent and residual thionyl chloride were removed under reduced pressure to obtain 2.2 g of the product with a yield of 90%.

[0264]The second step reaction: 4-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-di Preparation of methyl-1H-pyrazol-5-yl 7-chloro-3-methylquinoline-8-carboxylate: at room temperature, (2-chloro-4-(methylsulfonyl)-3- ((2,2,2-t...

technical field

[0001] The invention relates to the technical field of herbicides, in particular to a pyrazole compound and its salt and use. Background technique

[0002] Weeds in farmland are the enemy of crops. Weeds have strong reproductive ability and compete with crops for sunlight, water and fertilizer. According to statistics, crops in the world lose an average of 12% of their output every year due to weed damage. Therefore, the control of weeds is the most important An important part of efficient farming. The use of chemical agents to weed control is the most effective and labor-saving method among many weed control methods. Although there are various types of herbicides on the market, due to the continuous expansion of the market, the resistance of weeds and the service life of drugs, and people's increasing attention to the environment, people still need to continuously develop new high-efficiency, safe and economical herbicides New varieties. Therefore, new he...

Examples

Embodiment 1

[0245] 4-(2-Chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-dimethyl-1H- Preparation of pyrazol-5-ylquinoline-8 carboxylate (compound 1)

[0246]

[0247] The first step reaction: the preparation of 1,3-dimethyl-1 hydrogen-pyrazol-5-ol: add methyl acetoacetate (13.0g, 0.1mol) dropwise to methanol (70ml) solution at room temperature A solution of hydrazine (4.66 g, 0.101 mol) in methanol (6 ml) was added dropwise for 20 minutes, during which the temperature of the solution rose to 45°C. The reaction solution was heated to reflux, dehydrated by a dehydrator, and reacted at reflux for 2 hours, monitored by a TLC plate, and a small amount of raw materials remained. An appropriate amount of solvent was removed under reduced pressure, ethyl acetate / petroleum ether (1:2) was added to make a slurry, and filtered to obtain 10.6 g of a red solid product, yield: 93%. LC-MS [M+H]+=113.07, [M+Na]+=135.05, [M+K]+=151.02.

[0248] The second step reaction: the p...

Embodiment 2

[0256] 4-(2-Chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-dimethyl-1H- Preparation of pyrazol-5-yl 3,7-dichloroquinoline-8-carboxylate (compound 9)

[0257]

[0258] The first step reaction: the preparation of 3,7-dichloroquinoline-8-acyl chloride: at room temperature, 3,7-dichloroquinoline-8-carboxylic acid (2.85g, 0.01mol), dichloroethane (60ml) and N, N-dimethylformamide (0.1 g) were added into a three-necked flask, and thionyl chloride (2.38 g, 0.02 mol) was added dropwise to the above mixture. Heat to reflux for 5 hours. Heating was stopped, and the solvent and residual thionyl chloride were removed under reduced pressure to obtain 2.2 g of the product with a yield of 86%.

[0259] The second step reaction: 4-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-di Preparation of methyl-1H-pyrazol-5-yl 3,7-dichloroquinoline-8-carboxylate: at room temperature, (2-chloro-4-(methylsulfonyl)-3-((2 ,2,2-trifluoroethoxy)meth...

Embodiment 3

[0261] 4-(2-Chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-dimethyl-1H- Preparation of pyrazol-5-yl 7-chloro-3-methylquinoline-8-carboxylate (compound 10)

[0262]

[0263] The first step reaction: the preparation of 7-chloro-3-methylquinoline-8-acid chloride: at room temperature, 7-chloro-3-methylquinoline-8-carboxylic acid (2.33g, 0.01mol), di Ethyl chloride (60ml) and N,N-dimethylformamide (0.1g) were added into a three-necked flask, and thionyl chloride (2.38g, 0.02mol) was added dropwise to the above mixture. Heat to reflux for 5 hours. Heating was stopped, and the solvent and residual thionyl chloride were removed under reduced pressure to obtain 2.2 g of the product with a yield of 90%.

[0264]The second step reaction: 4-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-di Preparation of methyl-1H-pyrazol-5-yl 7-chloro-3-methylquinoline-8-carboxylate: at room temperature, (2-chloro-4-(methylsulfonyl)-3- ((2,2,2-t...

Images