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4-benzoyl pyrazole compound with herbicidal activity

A technology of benzoylpyrazoles and herbicidal activity is applied in the directions of organic chemistry, herbicides and algicides, chemicals used for biological control, etc., and can solve the problems of insufficient herbicidal activity and crop safety, etc., achieve good selectivity

Active Publication Date: 2014-08-13
QINGDAO KINGAGROOT CHEM COMPOUNDS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, these known benzoylpyrazoles generally do not have sufficient herbicidal activity or sufficient crop safety

Method used

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  • 4-benzoyl pyrazole compound with herbicidal activity
  • 4-benzoyl pyrazole compound with herbicidal activity
  • 4-benzoyl pyrazole compound with herbicidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The synthesis of 4-(2-methylsulfonyl-4-trifluoromethylphenyl)-1,3-dimethyl-5-ethoxyacyloxypyrazole (compound number 001) is as follows:

[0047]

[0048] Add 2.5 g (0.022 mol) of 1,3-dimethyl-5-hydroxypyrazole and 30 mL of toluene into a three-necked flask, and add 9.0 g of triethylamine (0.09 mol) while stirring. Control the temperature in an ice bath at 5-10°C, add dropwise a toluene solution of 6.3g (0.022mol) of 2-methylsulfonyl-4-trifluoromethylbenzoyl chloride, and control the reaction temperature not to exceed 15°C. Ice-water bath, stirred at room temperature for 30min, TLC detection reaction (ethyl acetate:petroleum ether=4:1, GF254, UV color development), after the reaction is complete, add 0.2g of 2-methyl-2-hydroxypropionitrile, stir Slowly heat up to 45-50°C for reaction, TLC detection reaction (ethyl acetate:petroleum ether=2:1, GF254, UV color development), after the reaction is complete, cool to room temperature, dropwise add ethyl chloroformate 2.5g (...

Embodiment 2

[0049]Example 2: 4-(2-methylsulfonyl-4-trifluoromethylphenyl)-1-methyl-3-trifluoromethyl-5-(2-chloronicotinoyloxy)pyrazole (compound number 002 ), the synthetic reaction formula is as follows:

[0050]

[0051] Add 3.0 g (0.018 mol) of 1-methyl-3-trifluoromethyl-5-hydroxypyrazole and 30 mL of acetonitrile into a three-necked flask, and add 8.0 g of triethylamine (0.08 mol) while stirring. Control the temperature in an ice bath at 5-10°C, add dropwise acetonitrile solution of 5.0g (0.018mol) of 2-methylsulfonyl-4-trifluoromethylbenzoyl chloride, control the reaction temperature not to exceed 15°C, remove the Ice-water bath, stirred at room temperature for 30min, TLC detection reaction (ethyl acetate:petroleum ether=4:1, GF254, UV color development), after the reaction is complete, add 0.1g of sodium cyanide, and slowly heat up to 35-45°C under stirring Reaction, TLC detection reaction (ethyl acetate:petroleum ether=2:1, GF254, UV color development), after the reaction is co...

Embodiment 3

[0052] Example 3: 4-(2-methylsulfonyl-4-trifluoromethylphenyl)-1-methyl-3-difluoromethyl-5-(4-methoxyphenoxyacetoxy)pyrazole ( Synthesis of Compound No. 003)

[0053] The synthetic reaction formula is as follows:

[0054]

[0055] Add 3.0 g (0.02 mol) of 1-methyl-3-difluoromethyl-5-hydroxypyrazole and 50 mL of dichloromethane into a three-necked flask, and add 9.0 g of triethylamine (0.09 mol) while stirring. Control the temperature in an ice bath at 5-10°C, add dropwise a solution of 5.7g (0.02mol) of 2-methylsulfonyl-4-trifluoromethylbenzoyl chloride in dichloromethane, control the reaction temperature not to exceed 15°C, and complete the dropwise addition , remove the ice-water bath, stir at room temperature for 30 minutes, TLC detection reaction (ethyl acetate:petroleum ether=4:1, GF254, UV color development), after the reaction is complete, add 0.2g of 2-methyl-2-hydroxypropionitrile, While stirring, the temperature was slowly raised to reflux reaction, and the react...

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Abstract

The invention relates to a 4-benzoyl pyrazole compound with herbicidal activity. The structural formula of the 4-benzoyl pyrazole compound with the herbicidal activity is as shown in specifications, wherein R1 in the structural formula is selected from hydrogen, methyl or ethyl, R2 in the structural formula is selected from methylsulfonyl, methoxyl, methylthio, fluorine, chlorine or cyan, R3 in the structural formula is selected from hydrogen, methyl, methyl fluoride, difluoromethyl or trifluoromethyl, R in the structural formula is selected from a five-membered heteroaromatic ring, a six-membered heteroaromatic ring, C1-C6 alkoxyl, aromatic hetero-oxy, six-membered aryloxy or six-membered aromatic amino, and hydrogen in the C1-C6 alkoxyl can be replaced by fluorine or chlorine; m and n are selected from 0 or 1 and cannot be 1 at the same time. A series of relatively efficient weed killers and plant growth regulators with relative good selectivity and safety are synthesized by introducing a fluorine-containing functional group to a pyrazole 3-site and chemically modifying a pyrazole 5-site.

Description

technical field [0001] The invention relates to a 4-benzoylpyrazole compound as an active ingredient of a herbicide. Background technique [0002] U.S. Patent No. 4,643,757 discloses 1-methyl-4 benzoylpyrazole as a herbicide, preferably with halogen, nitro or sulfonylmethyl at the 2-position of the benzene ring, and with hydrogen, halogen, or methyl at the 3-position of the benzene ring. group, and the 4th position has a halogen or sulfonylmethyl group. Chinese patent CN01807555.X discloses a class of benzoylpyrazoles and their application as herbicides for the control of some broad-leaved weeds in grains. Chinese patent CN97194093.2 discloses a class of benzoylpyrazole herbicides, preferably the 3-position of pyrazole is a cyclopropanyl group. [0003] However, these known benzoylpyrazoles generally do not have sufficient herbicidal activity or sufficient crop safety. Contents of the invention [0004] The object of the present invention is to provide a new 4-benzoylpy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/18C07D401/12C07D405/12A01N47/06A01N43/40A01N43/56A01P13/00A01P21/00
CPCA01N43/56A01N47/06C07D231/20C07D401/12C07D405/12
Inventor 沈园园连磊征玉荣彭学岗金涛
Owner QINGDAO KINGAGROOT CHEM COMPOUNDS CO LTD
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