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2-pyrimidine oxy-n-ureido phenyl-benzyl amide compound, preparing method and use thereof

A technology of ureidophenylbenzylamine and pyrimidinyloxy, which is applied in the field of agricultural chemical herbicides and can solve the problems of limited varieties of new pesticides

Inactive Publication Date: 2005-06-29
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, at present, there are very limited varieties of new pesticides with independent intellectual property rights in my country. Therefore, the development of new pesticides is still a research topic for people.

Method used

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  • 2-pyrimidine oxy-n-ureido phenyl-benzyl amide compound, preparing method and use thereof
  • 2-pyrimidine oxy-n-ureido phenyl-benzyl amide compound, preparing method and use thereof
  • 2-pyrimidine oxy-n-ureido phenyl-benzyl amide compound, preparing method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] 1. Synthesis of intermediate (II)

[0054] (a) Synthesis of intermediate (II-1)

[0055] The first step: Take the synthesis of 1-p-nitrophenyl-3-diethylurea as an example: under the protection of argon, add 0.82 grams (5 mmol) of para Dissolve nitrophenyl isocyanate and 5 mL of anhydrous benzene, 0.57 mL (5.5 mmol) of diethylamine in 5 mL of anhydrous benzene, cool to 0-10 ° C, add dropwise to the reaction solution, stir for about 30 minutes after the addition, and spin dry , The pure product was obtained by column chromatography with a yield of 98%.

[0056] The second step: Nitro reduction: Dissolve 5 mmol 1-p-nitrophenyl-3-diethylurea in 20 mL of anhydrous methanol, add 90 mg (equivalent to 1-p-nitrophenyl-3-diethylurea The mass of 7.5%) Raney Ni, 0.469 g (7.5 mmol) of 80% hydrazine hydrate was added dropwise to the reaction solution, stirred at room temperature until the reaction was complete, and the end of the reaction was controlled by TLC. After filtration, t...

Embodiment 2

[0078] The synthesis of I-2, the detailed experimental steps are the same as in Example 1: (1) Condensation with salicylaldehyde: feeding amount 5.21mmol1-m-aminophenyl-3-diethylurea, filtered to obtain 1.620 grams of imines, yield 99%. (2) Schiff base reduction: the amount of imine charged was 5.21 mmol, and 1.630 g (5.21 mmol) of the product was obtained, with a yield of 99%. (3) Condensation with pyrimidine sulfone: 1.630 g (5.21 mmol) of the imine-reduced product was obtained by column chromatography (petroleum ether: ethyl acetate = 2:1) to obtain a pure product with a yield of 85%.

[0079] solid

[0080] m.p.: 100.4±0.5℃

[0081] 1 H NMR (300MHz, CDCl 3 / TMS): δ1.21 (6H, t, CH 3 , J=7.14Hz), 3.36 (4H, q, CH 2 , J=7.14Hz), 3.80 (6H, s, OCH 3 ), 4.34 (2H, s, CH 2 ,), 5.77 (1H, s, CH), 6.21-7.47 (8H, m, CH) MS (EI): 45 (m / z, 100), 452 (M+1, 2.01)

[0082] IR (KBr / cm -1 ): 3406 (γ N-H ), 3309 (γ N-H), 1639 (γ C＝O ), 1598, 1539, 1484 (γ C＝C ), 1572 (γ C＝N ), 1...

Embodiment 3

[0086] The synthesis of I-3, the detailed experimental procedure is the same as that of Example 1: (1) Condensation with 6-chlorosalicylaldehyde: feed amount 4mmol amino, spin dry and go directly to the next step, the yield is 99%. (2) Schiff base reduction: the amount of imine was 4 mmol, and 1.39 g (4 mmol) of the product was obtained, with a yield of 99%. (4) Condensation with pyrimidine sulfone: Synthesize by method b, feed amount 1.39 g (4 mmol) imine reduction product, column chromatography (petroleum ether: ethyl acetate=5: 1) to obtain pure product, yield 90% .

[0087] solid

[0088] m.p.: 153.6±0.5℃

[0089] 1 H NMR (300MHz, CDCl 3 / TMS): δ1.21 (6H, t, CH 3 , J=6.9Hz), 3.35 (4H, q, CH 2 , J=6.9Hz), 3.78 (6H, s, OCH 3 ), 4.43 (2H, d, CH 2 , J=2.7Hz), 5.75 (1H, s, CH), 6.17-7.30 (7H, m, CH)

[0090] MS (EI): 157 (m / z, 100), 485 (M + , 3.97)

[0091] IR (KBr / cm -1 ): 3418 (γ N-H ), 3300 (γ N-H ), 1637 (γ C＝O ), 1607, 1568, 1541 (γ C＝C ), 1694 (γ C＝N ), ...

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Abstract

The invention relates to a 2-pyrimidinyloxy-N-ureidophenylbenzylamine compound, a preparation method and an application as an agricultural chemical herbicide. Its structural formula is as follows: ∴ Among them: D or E = hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 haloalkoxy; X = hydrogen, halogen, nitro, Cyanide, carboxyl, ester, sulfonyl, C1-C8 alkanoylamino, C1-C8 haloalkanoylamino, C1-C8 alkanoyl, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, Phenyl, benzo, substituted phenyl or heterocyclic; R1, R2 = hydrogen, ester, sulfonyl, C1-C8 alkyl, C1-C8 substituted alkyl (halogen or alkoxy, etc. substituted alkyl) , C1-C8 alkanoyl, phenyl, substituted phenyl or heterocyclic groups such as pyridyl, thienyl, thiazolyl, pyrimidinyl; X' is H, ureido (the substituents on the ureido are R1 and R2), halogen atom, carboxyl, ester group, C1-C8 alkanoyl, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, phenyl, substituted phenyl or heterocyclic group, etc.; R3= Hydrogen, C1-C8 alkanoyl, C1-C8 haloalkanoyl, benzoyl, substituted benzoyl, C1-C8 alkyl.

Description

technical field [0001] The present invention relates to a new class of 2-pyrimidinyloxy-N-ureidophenylbenzylamine compounds, a preparation method and its use as an agrochemical herbicide. Background technique [0002] Pesticides are an indispensable means of production for human beings to obtain food and ensure stable and high yields in agriculture. In the past century, pesticides such as insecticides, fungicides, and herbicides have made great contributions to human beings. In recent years, with the continuous growth of the world population, human beings' demand for food is also increasing, but the growth rate of cultivated land is far behind the speed of population growth. To solve this worldwide problem, we must rely on increasing the food production per unit area. To increase yield and improve crop quality, various means must be adopted, such as breeding, cultivation, fertilization, etc., and the application of pesticides is also one of the essential means. However, it ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/34A01N47/36A01N47/30C07D239/62
CPCC07D239/62A01N47/30
Inventor 吕龙陈杰吴勇金志平徐小燕袁军张艳王永华
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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