[N-(2-pyrimidine oxy) benzylamino phenyl] sulfamine compound, and its preparing method and use

A kind of technology of benzylaminophenyl and sulfonamide, applied in the field of new [N-benzylaminophenyl]sulfonamide compounds

Inactive Publication Date: 2007-10-17
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although pyrimidine salicylates have high herbicidal activity, they are currently only suitable for weed control in cotton fields and rice fields

Method used

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  • [N-(2-pyrimidine oxy) benzylamino phenyl] sulfamine compound, and its preparing method and use
  • [N-(2-pyrimidine oxy) benzylamino phenyl] sulfamine compound, and its preparing method and use
  • [N-(2-pyrimidine oxy) benzylamino phenyl] sulfamine compound, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesis of [N-(2-pyrimidinoxy)benzylaminophenyl]sulfonamides

[0050] Take I-4 synthesis as an example:

[0051] The first step: sulfonylation: add (5mmol) saturated potassium carbonate solution, 221.5mg (1.0mmol) p-nitrobenzenesulfonyl chloride and 123mg (1.0mmol) o-methoxyaniline in a three-necked flask of a 100mL dropping funnel, and heat To 60-70°C, stir for about 2 hours after the addition is complete, filter the filter cake to obtain 292 mg of 4-nitrobenzenesulfonyl (2'-methoxy) aniline, with a yield of 95%.

[0052] Step 2: Nitro reduction: Dissolve 292 mg of 4-nitrobenzenesulfonyl (2'-methoxy) aniline in 20 mL of anhydrous methanol, and add 30 mg (equivalent to 4-nitrobenzenesulfonyl (2'-methyl) The mass of oxy)aniline 10%) Raney Ni, 100 mg (1.5 mmol) of 80% hydrazine hydrate was added dropwise to the reaction solution, stirred at room temperature until the reaction was complete, and TLC controlled the end of the reaction. After filtration, the filtrate was spin-d...

Embodiment 2

[0066] For the synthesis of I-1, the detailed experimental procedure is the same as that of Example 1: (1) Sulfonylation: the feeding amount is 6 mmol n-butylamine to obtain 1.4 g of the product, and the yield is 90%. (2) Nitro reduction: 6mmol of sulfonylated product was added in the feed amount, and the product was spin-dried directly into the next step with a yield of 99%. (3) Condensation with salicylaldehyde: the feeding amount is 6mmol of amino compound, which is spin-dried directly to the next step, the yield is 99%. (4) Reduction with Schiff base: 6 mmol imines were charged to obtain 1.82 g (5.44 mmol) of product, with a yield of 90%. (5) Condensation with 4,6-dimethoxy-2-methylsulfonyl pyrimidine: Using acetonitrile as solvent, synthesize at 40-50°C, feed amount 1.82g (5.44mmol) product of imine reduction, column layer After analysis (petroleum ether: ethyl acetate = 3:1), the pure product was obtained, and the yield was 95%.

[0067] Solid

[0068] m.p.: 132.2±0.5°C

[0...

Embodiment 3

[0075] For the synthesis of I-2, the detailed experimental procedure is the same as in Example 1: (1) Sulfonylation: The feed amount is 6 mmol di-n-butylamine to obtain 1.82 g of the product, with a yield of 97%. (2) Nitro reduction: 6mmol of sulfonylated product was added. In this step, when RaneyNi was filtered, it was washed several times with chloroform, and the yield was 99%. (3) Condensation with salicylaldehyde: the feeding amount is 6mmol of amino compound, which is spin-dried directly to the next step, the yield is 99%. (4) Reduction with Schiff base: 6mmol of imine was added to obtain 2.214g (5.671mmol) of product with a yield of 95%. (5) Condensation with 4,6-dimethoxy-2-methylsulfonyl pyrimidine: Using acetonitrile as a solvent, synthesis at 40-50°C, the amount of charge is 2.214 g (5.671 mmol) of the product of imine reduction, column layer After analysis (petroleum ether: ethyl acetate=2:1), the pure product was obtained, and the yield was 87%.

[0076] Solid

[0077...

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Abstract

This invention relates to a group of compounds [N-(2-pyrimidinyloxy) benzyl amino phenyl] sulfonamide. In the general formula as shown right, D or E = C1~C4 alkoxyl or C1~C4 halogenated alkyloxyl; X= H, halogens, nitro, C1~C8 alkyl, C1~C8 halogenated alkyl and C1~C8 alkyloxyl; R1, R2= H, halogens, nitro, phenyl, halogenated or C1~C4 alkyl-substituted phenyl or heterocyclic radical which includes pyridyl, thienyl, thiazyl and pyrimidinyl.

Description

Technical field [0001] The invention relates to a new class of [N-(2-pyrimidinoxy)benzylaminophenyl]sulfonamide compounds, a preparation method and their use as agrochemical herbicides. Background technique [0002] Pesticides are an indispensable means of production for humans to obtain food and ensure stable and high yields in agriculture. In the past century, pesticides such as pesticides, fungicides, and herbicides have made great contributions to mankind. In recent years, with the continuous growth of the world’s population, human needs for food are also increasing, but the growth rate of arable land is far behind the rate of population growth. To solve this worldwide problem, we must rely on increasing the amount of food per unit area. Yield and improvement of crop quality require various methods, such as breeding, cultivation, fertilization, etc., and the application of pesticides is also one of the indispensable methods. However, it should be noted that while pesticides h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/34A01N43/54
Inventor 吕龙陈杰唐庆红吕强徐小燕金志平景竹黄玉
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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