(2-pyrimidine oxygen base)benzaldehyde hydrazone compounds, preparation method and uses thereof

A kind of technology of benzaldehyde hydrazone and pyrimidineoxy, applied in the field of agrochemical herbicides

Inactive Publication Date: 2009-02-18
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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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

Method used

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  • (2-pyrimidine oxygen base)benzaldehyde hydrazone compounds, preparation method and uses thereof
  • (2-pyrimidine oxygen base)benzaldehyde hydrazone compounds, preparation method and uses thereof
  • (2-pyrimidine oxygen base)benzaldehyde hydrazone compounds, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of (2-pyrimidinyloxy)benzaldehyde hydrazones

[0046] Take 1 synthesis as an example:

[0047] The first step: Condensation with 4,6-dimethoxy-2-thiamphenicol pyrimidine: 15.6g (0.1mol) 6-chloro salicylaldehyde, 21.8g (0.1mol) 4,6-dimethoxy - 2-thiamphenicol pyrimidine, react with 41.4g (0.3mol) of anhydrous potassium carbonate in 150mL of acetonitrile in an oil bath at 40°C for 8-9h, and control the end point of the reaction by TLC. After filtration and spin-drying, petroleum ether and ethyl acetate were recrystallized to obtain 15.4 g of pure product with a yield of 69.3%.

[0048] The second step: Condensation with pyrimidine salicylaldehyde: Dissolve 286mg (1.6mmol) m-chlorophenylhydrazine hydrochloride in a mixed solvent of ethanol and water, add dropwise 0.25ml (1.8mmol) triethylamine to dissolve m-chlorophenylhydrazine free out. Then 470mg (1.6mmol) of 6-chloropyrimidine salicylaldehyde was added to the reaction solution, and stirred at room temperat...

Embodiment 2

[0055] 2, the detailed experimental steps are the same as in Example 1: (1) Condensation with 4,6-dimethoxy-2-thiamphenicol pyrimidine: 0.1mol6-chloro salicylaldehyde in charge, 15.4g of product is obtained, yield 69.3%. (2) Condensation with pyrimidine salicylaldehyde: feed amount 1.6 mmol o-chlorophenylhydrazine hydrochloride, recrystallization from petroleum ether and ethyl acetate to obtain 230 mg of pure product, yield 36.1%.

[0056] solid

[0057] m.p.: 133.6±0.5℃

[0058] 1 H NMR (300MHz, DMSO): δ 3.74 (6H, s, OCH 3 ), 5.96 (1H, s, CH), 6.73-7.48 (7H, m, CH), 8.53 (1H, s, CH), 10.12 (1H, s, NH)

[0059] MS (ESI): 419 (M+H + ), 441 (M+Na + ), 473 (M+MeOH+Na + )

[0060] E.A. for C 19 h 16 Cl 2 N 4 o 3

Embodiment 3

[0062] 3, the detailed experimental steps are the same as in Example 1: (1) condensation with 4,6-dimethoxyl-2-thiamphenicol pyrimidine: feeding amount 0.1mol6-chloro salicylaldehyde, product 15.4g, yield 69.3%. (2) Condensation with pyrimidine salicylaldehyde: feed amount 1.6 mmol p-chlorophenylhydrazine hydrochloride, recrystallization from petroleum ether and ethyl acetate to obtain 257 mg of pure product, yield 40.3%.

[0063] 1 H NMR (300MHz, DMSO): δ 3.74 (6H, s, OCH 3 ), 5.96 (1H, s, CH), 6.71-7.44 (7H, m, CH), 8.53 (1H, s, CH), 10.14 (1H, s, NH)

[0064] MS (ESI): 419 (M+H + ), 441 (M+Na + ), 473 (M+MeOH+Na + )

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Abstract

The present invention relates to a (2-pyrimidinyloxy) benzaldehyde hydrazone compound, a preparation method thereof, and an application thereof as a chemical weed killer in the agriculture. The compound has a general structural formula as shown on the right, wherein, D or E is halogen, hydroxyl, C1-C4 alkoxyl or C1-C4 halogenating alkoxyl; X is hydrogen, halogen, nitryl, C1-C8 alkyl, C1-C8 halogenating alkyl, or C1-C8 alkoxyl; and R1 or R2 is hydrogen, C1-C8 alkyl, benzyl, R3 substituted benzyl, R3 substituted heterocyclic group, alkyl acyl, R3 substituted heterocyclic acyl group, alkyl sulphonyl. R3 substituted benzene or R3 substituted heterocyclic sulphonyl. R1R2N can also be cyclohexylamine or n-amylamine. R3 is hydrogen, halogen, nitryl, cyano, carboxyl, ester group, sulphonyl, C1-C8 alkoxy amido, C1-C8 halogenating alkoxy amido, C1-C8 alkyloxyacyl, C1-C8 alkyl, C1-C8 halogenating alkyl, C1-C8 alkoxyl, benzyl, benzo or heterocyclic group.

Description

technical field [0001] The invention relates to a new class of (2-pyrimidinyloxy) benzaldehyde hydrazone compounds, a preparation method and an application 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 indispensable means. However, i...

Claims

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Application Information

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IPC IPC(8): C07D239/34A01N43/54A01P13/00
Inventor 吕龙吕强唐庆红戴明付群梅
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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