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Uracil-based compounds, and herbicides comprising same

A compound, uracil technology, applied in the field of novel uracil compounds and their preparation, can solve the problem of herbicide loss and achieve high selective herbicidal effect and excellent herbicidal activity

Active Publication Date: 2011-09-28
FARMHANNONG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, research and development of new herbicides are continuing due to the occurrence of various weeds that still cause damage to agriculture.

Method used

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  • Uracil-based compounds, and herbicides comprising same
  • Uracil-based compounds, and herbicides comprising same
  • Uracil-based compounds, and herbicides comprising same

Examples

Experimental program
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Effect test

Embodiment approach

[0029] The uracil compound represented by the chemical formula 1 according to the present invention includes agrochemically acceptable salts, racemates, enantiomers or diastereomeric compounds of the compound represented by the chemical formula 1.

[0030] In addition, the uracil-based compound represented by the chemical formula 1 according to the present invention may be used in the form of an agrochemically acceptable salt. The agrochemically acceptable salts may include, for example, salts with metal salts, organic bases, inorganic acids, organic acids, basic or acidic amino acids, and the like. Suitable metal salts may include, for example, alkali metal salts such as sodium salts, potassium salts and the like; alkaline earth metal salts such as calcium salts, magnesium salts, barium salts and the like; aluminum salts and the like. Salts with organic bases may include, for example, with trimethylamine, triethylamine, pyridine, picoline, 2,6-lutidine, ethanolamine, diethano...

preparation example 1

[0114] [Preparation Example 1: Synthesis of 2-chloropropionyl chloride]

[0115] To a solution obtained by dissolving 10.8 g of 2-chloropropionic acid in 0.5 mL of dimethylformamide, 17.8 g of thionyl chloride (SOCl2) chloride was added dropwise at 50° C. for 30 minutes. After stirring at the same temperature for 7 hours, distillation was carried out at 112° C. to obtain 9.4 g of pale yellow oil.

[0116] 1 H NMR (CDCl 3 , 300MHz) δ 4.68 (q, 1H, J=7.0Hz), 1.84 (d, 3H, J=7.0Hz).

preparation example 2

[0117] [Preparation Example 2: Synthesis of 3-(2-chloropropionylamino)propionic acid methyl ester]

[0118] To a suspension in which 2.25 g of β-alanine methyl ester hydrochloride was suspended in 10 mL of methylene chloride was added 1.63 g of triethylamine, followed by stirring for 30 minutes. After adding 1.27 g of pyridine and cooling the reaction mixture to 0° C., 2.04 g of 2-chloropropionyl chloride was dissolved in 10 mL of methylene chloride and added dropwise for 20 minutes. The reaction mixture was stirred at room temperature for 2 hours, washed successively with water, 1N hydrochloric acid, saturated sodium bicarbonate, dehydrated, filtered, and concentrated to give 2.9 g of a yellow oil in 93% yield.

[0119] 1 H NMR (CDCl3 , 300MHz) δ7.15(br s, 1H), 4.41(q, 1H, J=7.0Hz), 3.74(s, 3H), 3.58(q, 2H, J=6.1Hz), 2.59(t, 2H, J=6.0 Hz), 1.74 (d, 3H, J=7.1 Hz).

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Abstract

The present invention relates to uracil-based compounds, to a method for producing the compounds, and to herbicides comprising the compounds as active ingredients. R1, R2, R3, R4, R5, X, Y, Z, and W are as defined in the detailed description of the invention. [Keywords] uracil, herbicides, pyrimidinedione.

Description

【Technical field】 [0001] The present invention relates to a novel uracil compound, a preparation method thereof, and a herbicide comprising the same. 【Background technique】 [0002] In general, control of weeds is very important for improving agricultural productivity, and various herbicides have been used in the past. [0003] Triazine-based herbicides such as Atrazine or anilide-based herbicides such as Alachlor or Metolachlor have been used in corn cultivation in the past. On the other hand, conventional herbicides such as paraquat and glyphosate have been used as non-selective herbicides. [0004] However, research and development of new herbicides are continuing due to the occurrence of various weeds that still cause damage to agriculture. [0005] A compound represented by the following chemical formula A is disclosed in Japanese Laid-Open Patent No. 2000-302,764 in relation to an active substance of a herbicide. [0006] [0007] In said formula A, R1 is a hydro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/54
CPCC07D239/54A01N43/54A01N41/06
Inventor 高荣宽郑谨会柳在旭禹在春丘桐完金大璜金台埈崔寅永金荣权吴泰铉崔埈赫石美英金庚星郑奉真
Owner FARMHANNONG CO LTD
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