Uracil weeding compounds introducing amide structure

A technology of uracil and compounds, which is applied in the field of uracil herbicidal compounds and can solve problems such as poor activity

Inactive Publication Date: 2008-07-30
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Trifluoromethyl is a very important substituting group, and its introduction is greatly beneficial to the improvement of activity. As reported in US 4927451, EP 473551, JP 03215476, and EP 3712782, the 6-position is methyl, phenyl or ring-connected The activities of compounds 5, 6, 7, and 8 are all worse than those of trifluoromethyl analogues

Method used

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  • Uracil weeding compounds introducing amide structure
  • Uracil weeding compounds introducing amide structure
  • Uracil weeding compounds introducing amide structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Example 1: 3-chloro-N-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidine Preparation of -1(6H)-yl)phenyl)-2,2-dimethylpropanamide (compound 1-05).

[0084] 1.35 g (4.0 mmol) of intermediate 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2 was added to a 100 mL round bottom flask, 4(1H,3H)-diketone, 30mL dichloroethane and 0.45g (4.4mmol) triethylamine, magnetically stirred, under ice-water cooling, slowly added dropwise 0.62g (4.0mmol) chloropivaloyl chloride, Dropwise reaction at room temperature for 2h. 100 mL of water was added to the reaction solution, and the organic layer was separated. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, precipitated under reduced pressure, and subjected to silica gel column chromatography to obtain 1.34 g of light yellow solid 3-chloro-N -(2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydrop...

Embodiment 2

[0086] Example 2: N-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidine-1(6H )-yl)phenyl)-2-(3-fluorophenoxy)propionamide (compound 1-09).

[0087] 1.35 g (4.0 mmol) of intermediate 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2 was added to a 100 mL round bottom flask, 4(1H,3H)-diketone, 30mL dichloroethane and 0.45g (4.4mmol) triethylamine, magnetically stirred, under ice water cooling, slowly drop 0.8g (4.0mmol) 2-m-fluorophenoxy Propionyl chloride, dropwise reaction at room temperature for 2h. 100mL of water was added to the reaction solution, and the organic layer was separated. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, precipitated under reduced pressure, and subjected to silica gel column chromatography to obtain 1.44g of a light yellow viscous substance, N- (2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1...

Embodiment 3

[0089] Example 3: N-(4-chloro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl) Preparation of phenyl)-2-(2,4-di-chlorophenoxy)propanamide (compound 1-21).

[0090] Into a 100 mL round bottom flask was added 1.28 g (4.0 mmol) of the intermediate 3-(5-amino-4-di-chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl)pyrimidine- 2,4(1H,3H)-diketone, 30mL dichloroethane and 0.45g (4.4mmol) triethylamine, magnetically stirred, under ice-water cooling, slowly add 1.01g (4.0mmol) 2-(2 , 4-di-chlorophenoxy) propionyl chloride, dropwise reaction at room temperature for 2h. 100 mL of water was added to the reaction solution, and the organic layer was separated. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, precipitated under reduced pressure, and subjected to silica gel column chromatography to obtain 1.64 g of light yellow solid N-(4- Chloro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimi...

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Abstract

The invention discloses a uracil herbicidal compound introducing amide structure shown by the general formula (I). X are hydrogen, fluorin, and chlorine; Y are hydrogen, fluorin, and chlorine; R<1> is hydrogen, C1-C4 alkyl, C1-C4 halogenated alkyl; R<2> is hydrogen, C1-C4 alkyl, C1-C4 halogenated alkyl; Q is C1-C4 halogenated alkyl, phenyl, substituted phenyl, C1-C4 dilute oxyl, C1-C4 alkyne, C1-C4 alkyl, alkoxy, C1-C4 alkylthio, C1-C4 alkoxycarbonyl, halogen, nitryl, substituted phenoxy, substituted pyridyloxy, Alpha- naphthyloxy. The compound of the general formula (I) exhibits better herbicidal activity against broadleaf weeds such as abutilon, pigweed, and emarginate amaranth and has a control efficiency of more than 80 percent at the dosage of 75g ai/ha in soil treatment before seedling or stem treatment after seedling; the product can also prevent monocotyledonous weeds such as crabgrass, barnyard grass, green bristlegrass, etc.

Description

technical field [0001] The invention relates to a uracil herbicidal compound introduced with an amide structure and a preparation method thereof. Background technique [0002] It has been reported in the literature that uracil protoporphyrinogen oxidase inhibitors have high-efficiency herbicidal activity, and there have been many patent reports abroad. The development of this type of herbicide began in the 1960s, when Du-pont developed a series of new varieties in this field, such as bromacil (bromacil, 1) and isocil (isocil, 2) in 1962. Developed, specific grass set (terbacil, 3) and so on were developed in 1966. In 1986, EP 0195346 reported DCMD (4), which introduced a trifluoromethyl group at the 6-position of uracil and a multifunctional phenyl group at the 3-position. Trifluoromethyl is a very important substituting group, and its introduction is greatly beneficial to the improvement of activity. As reported in US 4927451, EP 473551, JP 03215476, and EP 3712782, the 6...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54A01N43/54A01P13/00
Inventor 黄明智任叶果黄路雷满香胡礼柳爱平欧晓明项军王晓光刘兴平
Owner HUNAN CHEM RES INST
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