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Bispyribac derivative, and preparation method and application of bispyribac derivative

A technology of bispyribac and derivatives, applied in the field of bispyribac derivatives and their preparation, can solve the problems of no research and development reports on herbicidal activity and the like

Inactive Publication Date: 2017-11-03
武汉华邦化学新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] There is no research and development report on the herbicidal activity of 2-(pyridin-2-yl)ethyl-2,6-bis((4,6-dimethoxypyridin-2-yl)oxy)benzoate

Method used

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  • Bispyribac derivative, and preparation method and application of bispyribac derivative
  • Bispyribac derivative, and preparation method and application of bispyribac derivative
  • Bispyribac derivative, and preparation method and application of bispyribac derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The m.p.63-65°C of intermediate 1 (literature value m.p.64-66°C), yield: 45.5%, the m.p.146-149°C of intermediate 2 (literature value m.p.146-148°C), yield: 90.0%; The m.p. of intermediate 3 is 151-152°C, yield: 70.0% (literature melting point value: 150-152°C).

Embodiment 2

[0026] Synthesis of intermediate 4: 4.3g (10.0mmol) of intermediate 3 was dissolved in 60mL of toluene, 3.54g (30.0mmol) of thionyl chloride was added, refluxed for 4.0h, after cooling, toluene and excess Thionyl chloride was used directly in the next step.

Embodiment 3

[0028] Synthesis of compound 2-(pyridin-2-yl)ethyl-2,6-bis((4,6-dimethoxypyridin-2-yl)oxy)benzoate: 0.61g (5.0mmol) 2-Pyridyl ethanol was dissolved in 30 mL of dichloromethane, 5.0 mmol of triethylamine and a catalytic amount of 4-dimethylaminopyridine (DMAP) were added, and after stirring for 5 min, 2.69 g (5.0 mmol) of acid chloride 4 was added dropwise. 10mL of dichloromethane solution, TLC detection of raw material reaction is complete, the organic layer was washed with dilute hydrochloric acid, washed with saturated brine, dried, and solvent removal. Column chromatography of the crude product yielded 1.40 g of white solid 2-(pyridin-2-yl)ethyl-2,6-bis((4,6-dimethoxypyridin-2-yl)oxy)benzoate , m.p.82-85°C, yield 86.3%. 1 H NMR (400MHz, CDCl 3 )δ: 8.58 (s, 1H, pyridine), 7.94 (s, 1H, pyrimidine), 7.64 (dd, J = 19.4, 11.5Hz, 2H, C 6 h 3 , pyridine), 7.36 (s, 1H, C 6 h 3 ), 7.26–7.18 (m, 3H, pyrimidine), 6.97 (s, 1H), 5.76 (s, 2H), 4.83 (t, J = 6.6Hz, 2H, CH 2 ),3.80(s...

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PUM

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Abstract

The invention discloses a bispyribac derivative, and a preparation method and an application of the bispyribac derivative. The bispyribac derivative has the following structure as shown in the specification. The preparation method particularly comprises the following steps of: taking 2,6-dihydroxy-benzoic acid as a raw material for multi-step reactions to synthesize bispyribac (acid), then preparing bispyribac acyl chloride, further performing esterification reaction with 2-pyridyl ethanol to synthesize the bispyribac derivative, namely 2-(pyridine-2-yl) ethyl-2,6-bi((4,6-dimethoxy pyridine-2-yl) oxy) benzoate. The compound has better weeding activity and especially has better removal activity on a dicotyledonous weed, namely sisymbrium sophia, and the preparation method is simple to operate and higher in yield.

Description

technical field [0001] The present invention relates to a class of new compounds and their uses, specifically a bispyribac derivative and its preparation method and application. Background technique [0002] Pyrimidine salicylate herbicides are new inhibitors of acetolactate synthase (ALS) developed in the 1990s, with super high efficiency (the dosage is only 30-80ga.i. / hm 2 ), good safety and wide herbicidal spectrum. It was discovered through structural optimization on sulfonylurea herbicides, which overcomes the disadvantages of slow degradation of sulfonylurea herbicides and causing phytotoxicity to subsequent crops. , Sumitomo Chemical, Korea Institute of Chemical Technology and Syngenta have successively launched new varieties of pyriflubacin, bispyribac, saflufenacil and cyclopyramid. [0003] Shenyang Research Institute of Chemical Industry [Chinese patents CN101279950, CN101279951] developed compounds A1 and A2 based on the structure of pyrimidine salicylic acid in...

Claims

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Application Information

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IPC IPC(8): C07D401/14A01P13/00
CPCC07D401/14
Inventor 杨子辉田昊杨公振
Owner 武汉华邦化学新材料有限公司