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N-(2-pyrimidine oxygen based) benzyl amide compounds, preparation method and uses thereof

A technology of benzylamide and pyrimidinyloxy, 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

Pyrimidine salicylates have high herbicidal activity and are currently only suitable for weed control in cotton and rice fields

Method used

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  • N-(2-pyrimidine oxygen based) benzyl amide compounds, preparation method and uses thereof
  • N-(2-pyrimidine oxygen based) benzyl amide compounds, preparation method and uses thereof
  • N-(2-pyrimidine oxygen based) benzyl amide compounds, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of N-(2-pyrimidinyloxy)benzylamides

[0049] Take the synthesis of I-5 as an example: (o-chlorobenzoyl chloride)

[0050] Add 9.92g (81.3mmol) salicylaldehyde, 5.93g (85.3mmol) hydroxylamine hydrochloride and 7.51g (89.4mmol) sodium bicarbonate, ethyl acetate 100ml and about 8ml water in a 250mL three-necked flask, at room temperature, stir about overnight. Filtered, washed with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain 10 g with a yield of 89.7%.

[0051] Reduction to benzylamine: Dissolve 13.7g (0.1mol) of the product in 20mL of anhydrous methanol, pour it into a 250ml three-neck flask, add 40.8g (0.624mol) of zinc powder while stirring, and finally add 28.9g (0.458mol) of ammonium formate methanol solution. React overnight at room temperature. Adjust the pH to 3, filter, and adjust the filtrate to neutral with ammonia water, and a light yellow solid appears. Filter and dry. Obtained 7.9...

Embodiment 2

[0062] The synthesis of I-1, the detailed experimental steps are the same as in Example 1: (1) Reaction of 2-hydroxybenzylamine and isobutyryl chloride: feed 6 mmol of isobutyryl chloride to obtain 1.065 g of the product, with a yield of 92%. (2) Condensation with 4,6-dimethoxy-2-thiamphenicol pyrimidine, using acetonitrile as solvent, synthesized at 40-50°C. The pure product was obtained by column chromatography (petroleum ether: ethyl acetate = 3:1), with a yield of 90%.

[0063] solid

[0064] m.p.: 118-120°C

[0065] 1 H NMR (300MHz, CDCl 3 / TMS): δ 7.37-6.85 (4H, m, CH), 6.634 (1H, s, NH), 5.768 (1H, s, CH), 4.61-4.63 (2H, d, J=5.1Hz), 4.20 ( 1H, m, CH), 3.81 (6H, s, OCH 3 ), 2.52 (6H, s, CH 3 , J=7.2Hz)

[0066] MS (EI): 332 (M + , 100), 354 (M+Na + , 20)

[0067] E.A. for C 17 h 21 N 3 o 4

[0068] Calcd: C 61.62, H 6.39, N 12.68

[0069] Found: C 61.76, H 6.54, N 12.76

Embodiment 3

[0071] The synthesis of I-2, the detailed experimental steps are the same as in Example 1: (1) Reaction of 2-hydroxy-6-chlorobenzylamine with isobutyryl chloride: 6 mmol of isobutyryl chloride was fed to obtain 1.294 g of the product, with a yield of 95%. (2) Condensation with 4,6-dimethoxy-2-thiamphenicol pyrimidine, using acetonitrile as solvent, synthesized at 40-50°C. The pure product was obtained by column chromatography (petroleum ether: ethyl acetate = 3:1), with a yield of 85%.

[0072] solid

[0073] m.p.: 140-142°C

[0074] 1 H NMR (300MHz, CDCl 3 / TMS): δ 7.43-7.05 (3H, m, CH), 6.63 (1H, s, NH), 5.87 (1H, s, CH), 4.61-4.63 (2H, d, J=5.1Hz), 4.20 ( 1H, m, CH), 3.81 (6H, s, OCH 3 ), 2.52 (6H, s, CH 3 , J=7.2Hz)

[0075] MS(EI): 366(M + , 100), 388 (M+Na + , 20)

[0076] E.A. for C 17 h 20 ClN 3 o 4

[0077] Calcd: C 55.82, H 5.51, N 11.49

[0078] Found: C 55.90, H 5.65, N 11.65

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Abstract

The present invention relates to an N-(2-pyrimidinyloxy) benzyl amide compound, a preparation method thereof and an application thereof as a chemical weed killer in the agriculture. The compound has a 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; R is C1-C8 alkyl, R1 substituted benzyl or R1 substituted heterocyclic group, C1-C8 alkoxyl, R1 substituted benzyl or R1 substituted heterocyclic oxyl, R2 substituted amidogen and R3 substituted amidogen, R1 substituted benzyl or R1 substituted heterocyclic sulfonic acid amido; wherein, the R1 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, benzoyl, benzo, phenyl or heterocyclic group; R2 is hydrogen, C1-C8 alkyloxyacyl, C1-C8 halogenating alkyloxyacyl, benzoyl, benzoyl or C1-C8 alkyl; and R3 is ester group, sulphonyl, C1-C8 alkyl, C1-C8 halogenating alkyl, C1-C8 alkoxyl, C1-C8 alkyloxyacyl, phenyl or heterocyclic group.

Description

technical field [0001] The present invention relates to a new class of N-(2-pyrimidinyloxy)benzylamide compounds, a preparation method and its use as an agricultural chemical herbicide. Background technique [0002] Pyrimidinyloxybenzene derivatives can be used as chemical herbicides and have been reported in the literature for a long time, and representative examples include pyrithiobac-sodium (Pyrithiobac-sodium, KIH-2031, European patent 315889), bispyribac-sodium (Bispyribac- Sodium, KIH-2023, European patent 321846), pyriminobac-methyl (KIH-6127, Japanese patent 04368361), pyrimidine saflufenacil (Pyribenzoxim, European patent 658549) and cycloalifluoride (Pyriftalid, European patent 768034 ), [0003] Lu Long and others reported a new class of pyrimidinyloxybenzyl substituted arylamine derivatives, preparation methods and their application as agrochemical herbicides (ZL00130735.5, ZL01112689.2, ZL01113199.3, CN1513321A and CN1488626A ), which have very high herbicida...

Claims

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Application Information

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IPC IPC(8): C07D239/60C07D239/34A01N43/54A01P13/00
Inventor 吕龙唐庆红吕强许波苏强
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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