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Aryluracil compound or its pesticide acceptable salt, its preparation method, and herbicide composition

A technology of phenyluracil and compound, applied in the field of organic compounds, can solve the problems of narrow weed removal range, poor weed control effect and the like

Active Publication Date: 2021-11-02
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are some related new phenyluracil herbicides in recent years, there are disadvantages such as poor control effect on weeds and narrow range of weed removal.

Method used

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  • Aryluracil compound or its pesticide acceptable salt, its preparation method, and herbicide composition
  • Aryluracil compound or its pesticide acceptable salt, its preparation method, and herbicide composition
  • Aryluracil compound or its pesticide acceptable salt, its preparation method, and herbicide composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] The preparation method of the phenyluracil compound shown in compound number (1) in the table 1 of embodiment 1:

[0093] The phenyluracil compound shown in the compound number (1) is shown in formula (1), Its preparation process includes:

[0094] (1) Preparation of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidine-1(6H)- base) benzoyl chloride, the 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidine-1 (6H)-base) benzoyl chloride such as the compound shown in chemical formula A1:

[0095]

[0096] 2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzene Add formic acid (Ⅴ) (1.83g, 0.005mol) into 30mL of dichloromethane, stir for half an hour; then slowly add oxalyl chloride (1.90g, 0.015mol) dropwise, and then slowly add a few drops of N,N-dimethyl Methyl formamide (DMF), heated to reflux at room temperature for 3-5 hours, and spin-dried to obtain the target p...

Embodiment 2

[0113] The preparation method of the phenyluracil compound shown in compound number (27) in embodiment 2 table 1:

[0114]The phenyluracil compound shown in the compound number (27) is shown in formula (2), Its preparation process includes:

[0115] (1) Preparation of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidine-1(6H)- base) benzoyl chloride (A2):

[0116] 2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzene Formyl chloride (A2) (1.59g, 0.0041mol) was dissolved in 20mL of dichloromethane to prepare A2 solution.

[0117] (2) Preparation of 3-chloro-benzenesulfonamide (B2)

[0118] Add 3-chloro-benzenesulfonyl chloride (0.9g, 0.0043mol) into 15mL of tetrahydrofuran, stir with a magnetic stirrer for half an hour, then slowly add 5mL of ammonia water dropwise, and react at room temperature for 3h; 3-Chloro-benzenesulfonamide (B2) was obtained as a white solid (0.78 g, 0.0041 mol, yield 95%). T...

Embodiment 3

[0121] The preparation method of the phenyluracil compound shown in compound number (37) in the table 1 of embodiment 3:

[0122] The phenyluracil compound shown in the compound number (37) is shown in formula (3), Its preparation process includes:

[0123] (1) Preparation of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidine-1(6H)- base) benzoyl chloride (A3):

[0124] 2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzene Formyl chloride (0.335g) was dissolved in dichloromethane to form A3 solution;

[0125] (2) Preparation of 3-(aminosulfonyl) methyl benzoate (B3):

[0126] Wherein, the preparation process of the 3-(aminosulfonyl) methyl benzoate (B3) refers to the reaction formula (C2), including:

[0127]

[0128] Add 3-(chlorosulfonyl)benzoic acid (3.97g) into a one-necked flask equipped with a magnetic stirrer, add a small amount of dichloromethane, then add 6.9g of oxalyl chloride, add 5...

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Abstract

The present invention provides a phenyluracil compound or a pesticide acceptable salt thereof as shown in formula I: wherein, R 1 , R 2 independently selected from hydrogen, amino, C 1 -C 4 Alkyl or C 1 -C 4 Haloalkyl; X, Y are independently selected from hydrogen, halogen, nitro, amino, cyano, C 1 -C 4 Alkyl or substituted C 1 -C 4 the alkyl group; R 3 selected from hydrogen, cyano or C 1 -C 4 the alkyl group; R 4 Selected from cyano, nitro, substituted or unsubstituted phenyl, substituted or unsubstituted five-membered or six-membered aromatic heterocyclic groups or substituents shown in formula II; wherein, R 5 selected from halogen; R 6 , R 7 independently selected from hydrogen, halogen, C 1 -C 4 Alkyl or C 1 -C 4 haloalkyl. The compound has the characteristics of broad herbicidal spectrum and high herbicidal activity. The invention also provides a preparation method and herbicide composition of an aryl uracil compound or a pesticide acceptable salt thereof.

Description

technical field [0001] The invention relates to the technical field of organic compounds, in particular to aryl uracil compounds or their pesticide acceptable salts, their preparation method and herbicide composition. Background technique [0002] Because weeds compete with crops for glory and fertilizer, weeds cause great losses to crop production every year. The current method of controlling weeds is mainly to spray pesticides. With the widespread use of herbicides such as glyphosate, a large number of weeds have developed resistance, especially in plantations in southern China, goosegrass has become resistant to glyphosate and has become a dominant and malignant weed , in order to solve the increasingly serious weed problem, there is an urgent need to develop new herbicides with good weeding effect and low toxicity. Although there are some related new phenyluracil herbicides in recent years, they have disadvantages such as poor control effect on weeds and narrow range of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/54C07D405/12C07D409/12C07D401/12C07D413/12C07D403/12A01N43/54A01N43/80A01P13/00
CPCA01N43/54A01N43/80C07D239/54C07D401/12C07D403/12C07D405/12C07D409/12C07D413/12
Inventor 王明良尹春慧何雅慧罗秋晗阎思彤
Owner SHENZHEN UNIV