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Aryl uracil compounds, preparation method thereof and pesticide composition

A technology of aryl uracils and compounds, which is applied in the field of aryl uracil compounds and their preparation methods and pesticide compositions, can solve the problems of adverse effects on crop growth, narrow weed removal range, and poor killing effect, and achieve breastfeeding Low animal toxicity, strong herbicidal effect, and good control effect

Active Publication Date: 2019-08-02
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many kinds of herbicides on the market, which are generally used as non-selective herbicides, and generally have the characteristics of poor control effect, narrow weed removal range and high dosage, especially for malignant weeds such as goosegrass and barnyard grass The killing effect is poor
At the same time, as a selective herbicide, it often has adverse effects on the growth of crops, causing huge economic losses.

Method used

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  • Aryl uracil compounds, preparation method thereof and pesticide composition
  • Aryl uracil compounds, preparation method thereof and pesticide composition
  • Aryl uracil compounds, preparation method thereof and pesticide composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] The preparation method of the aryl uracil compounds shown in compound number 4 in table 1:

[0086] The aryluracil compound shown in the compound number 4 is shown in formula (1),

[0087] Its preparation process includes:

[0088] (1) 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoic acid (1.0g , 0.0026mol) into thionyl chloride, heated to reflux at room temperature for 6h, and spin-dried to obtain the target product 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-di Oxy-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride (0.8387 g, 0.0022 mol), 84% yield. The NMR hydrogen of the 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride The spectrum is characterized by: 1 H-NMR (600MHz, DMSO), the data is as follows, δ: 8.544 (d, J = 7.6Hz, 1H, Ar), 8.072 (d, J = 9.6Hz, 1H, Ar), 6.876 (s, 1H, CH) , 3.984(s,3H,-CH 3 ). Take 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluorometh...

Embodiment 2

[0093] The preparation method of the aryl uracil compounds shown in compound number 8 in table 1:

[0094] The aryluracil compound shown in the compound number 8 is shown in formula (2),

[0095] Its preparation method includes:

[0096] (1) 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoic acid (1.0g , 0.0026mol) into thionyl chloride, heated to reflux at room temperature for 6h, and spin-dried to obtain the target product 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-di Oxy-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride (0.8387 g, 0.0022 mol), 84% yield. The NMR hydrogen of the 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride The spectrum is characterized by: 1H-NMR (400MHz, DMSO), the data is as follows, δ: 8.544 (d, J = 7.6Hz, 1H, Ar), 8.072 (d, J = 9.6Hz, 1H, Ar), 6.876 (s, 1H,CH), 3.984(s,3H,-CH 3 ).

[0097] (2) Take 2-nitroethanol (0.0911g, 0.0010mol), 2-chloro-4-fluoro-5-...

Embodiment 3

[0100] The preparation method of the aryl uracil compounds shown in compound number 12 in table 1:

[0101] The aryluracil compound shown in the compound number 12 is shown in formula (3),

[0102] Its preparation method includes:

[0103] (1) Take 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoic acid (0.366g , 1mmol) was mixed with 3-aminopropanol (0.0751g, 1mmol), methanesulfonic acid (1mL, 15mmol) and alumina (0.27g, 3mmol) were added as a catalyst, heated to 80°C, and refluxed for 1h.

[0104] (2) Add ethyl acetate or dichloromethane to the crude product obtained in step (1), filter, wash three times with saturated sodium chloride and saturated sodium bicarbonate solution (1:1), separate liquids, and use anhydrous chlorinated Calcium was dried, filtered, and spin-dried to obtain a light yellow powdery solid (0.06g, 0.00014mol, yield 14.2% as shown in formula (3).

[0105] H NMR spectrum characterization: 1 H-NMR (400MHz, CDCl ...

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Abstract

The invention provides aryl uracil compounds shown in a formula I, wherein R1 and R2 are independently selected from hydrogen, amino, alkyl or halogenated alkyl, the carbon number of alkyl or halogenated alkyl is 1-4; X and Y are independently selected from hydrogen, halogen or cyano groups; Z is selected from oxygen atom or sulfur atom; when Z is the oxygen atom, R3 is C1-C8 alkyl substituted byfirst substituent groups, C2-C8 alkenyl substituted by the first substituent groups or C2-C8 alkynyl substituted by the first substituent groups; the first substituent groups comprise hydroxyl, nitryl, amino or alkyl amino; when Z is the sulfur atom, R3 is C1-C8 alkyl substituted by second substituent groups, C2-C8 alkenyl substituted by the second substituent groups or C2-C8 alkynyl substituted by the second substituent groups; the second substituent groups comprise hydroxyl, nitryl, amino, alkyl amino or alkoxycarbonyl. The aryl uracil compounds have high selectivity, wide weeding spectrum and good control effect on worst weed such as eleusine indica and the like. The invention also provides a preparation method of the aryl uracil compounds and pesticide composition.

Description

technical field [0001] The invention relates to the technical field of organic compounds, in particular to an aryl uracil compound, a preparation method thereof and a pesticide composition. Background technique [0002] Because weeds compete with crops for glory and fertilizer, weeds cause great losses to crop production every year. At present, the main method for controlling weeds is to spray herbicides. However, with the widespread application of herbicides (such as glyphosate), a large number of weeds have developed resistance, especially weeds such as goosegrass and barnyardgrass have developed into a dominant weed and a malignant weed. [0003] There are many kinds of herbicides on the market, which are generally used as non-selective herbicides, and generally have the characteristics of poor control effect, narrow weed removal range and high dosage, especially for malignant weeds such as goosegrass and barnyard grass The killing effect is poor. At the same time, as a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54A01N43/54A01P13/00A01P21/00
CPCA01N43/54C07D239/54
Inventor 王明良阎思彤尹春慧何雅慧谢晗鑫常超凡朱才镇徐坚马晨生
Owner SHENZHEN UNIV
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