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Amide compound and preparation method and application thereof

An amide compound and reaction technology, applied in the field of pesticides, can solve the problems of poor control effect on broad-leaved weeds, and achieve the effect of simple operation, high yield and good herbicidal activity

Active Publication Date: 2014-07-09
LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The common feature of existing amide herbicides is that almost all varieties control annual grassy weeds (monocotyledonous plants), and their control effect on broad-leaved weeds (including all dicotyledonous plants and some monocotyledonous plants) is poor

Method used

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  • Amide compound and preparation method and application thereof
  • Amide compound and preparation method and application thereof
  • Amide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Synthesis of compound I

[0022] Add 2 g of 2,4-dichlorophenoxyacetic acid and 8.8 mL of thionyl chloride into a 50 mL single-necked round-bottom flask, and carry out a reflux reaction at about 67°C under a magnetic stirrer for 3 hours to obtain a pungent PALE YELLOW LIQUID WITH ODOR. The reaction solution was distilled under reduced pressure in a water bath at 40°C under a vacuum of -0.07 Mpa to remove excess thionyl chloride to obtain 1.84 g of light yellow oily liquid, which was 2,4-dichlorophenoxyacetyl chloride (compound I: ).

[0023] (2) Synthesis of Compound II

[0024] Dissolve 1.84 g of 2,4-dichlorophenoxyacetyl chloride in 10 mL of tetrahydrofuran solvent, add 0.5 g of urea, heat on a constant temperature heating magnetic stirrer, and reflux at 70 °C for 5 h to obtain a yellow-white emulsion. Distill under reduced pressure in a water bath at 40°C under a vacuum of -0.07 Mpa to remove tetrahydrofuran and obtain white crystals. Dissolve the crystals wi...

Embodiment 2

[0026] Dissolve 1.84 g of 2,4-dichlorophenoxyacetyl chloride in 3.5 mL of pyridine solvent, add 0.75 g of urea, heat to 90°C in a water bath under a magnetic stirrer, and reflux for 5 hours to obtain a reddish-brown sticky substance. Distill under reduced pressure in a water bath at 70°C and a vacuum of -0.07 Mpa to remove pyridine to obtain a dark red solid, which was extracted 5 times with ethyl acetate. Ethyl acetate was removed by distillation under pressure to obtain white crystals. Dissolve the crystals with 20 mL of pyridine under the system conditions of 60°C, remove incompatible impurities by hot suction filtration, carry out vacuum distillation again at 75°C in a water bath, and vacuum -0.07 Mpa to remove pyridine, and recondense in dichloromethane to obtain the target product ( Compound II) 1.07 g, the yield is 60%.

Embodiment 3

[0028] Dissolve 1.84 g of 2,4-dichlorophenoxyacetyl chloride in 5 mL of tetrahydrofuran solvent, add 1.5 g of urea, heat to 70 °C, stir and reflux for 5 h, and obtain a yellow-white emulsion. Distill under reduced pressure in a water bath at 40°C under a vacuum of -0.07 Mpa to remove tetrahydrofuran and obtain white crystals. Dissolve the crystals with 20 mL of pyridine under the system conditions of 60°C, remove incompatible impurities by hot suction filtration, conduct vacuum distillation again at 75°C in a water bath, and vacuum degree -0.07 Mpa to remove pyridine, recrystallize in dichloromethane, and dry to obtain The target product (compound II) was 1.25 g, and the yield was 70%.

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Abstract

The invention discloses an amide compound. The amide compound has the following chemical structural formula. The structural formula is as shown in the specification. The preparation method comprises the following steps: reacting 2,4-dichlorbenzoxy acetyl chloride and urea to obtain the amide compound. The amide compound has excellent herbicidal activity, particularly the herbicidal activity on dicotyledon weeds is obviously superior to that of monocotyledon weeds. The preparation method of the amide compound is simple in operation and high in yield.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to an amide compound which can be used for weeding and its preparation method and application. Background technique [0002] Amide compounds are a class of herbicides widely used in production at present, with high efficiency and high selectivity. Judging from the period of use, amide herbicides can be divided into two categories: stem and leaf treatment agents, such as propanil and new swallow Ling, Fluoxachlor; soil treatment agents, such as alachlor, acetochlor, metolachlor, pretilachlor, gram chloramine, napropionamide, chlorpyramide, toxachlor, etc. The common feature of existing amide herbicides is that almost all varieties control annual grassy weeds (monocotyledonous plants), and their control effect on broad-leaved weeds (including all dicotyledonous plants and some monocotyledonous plants) is poor . Contents of the invention [0003] The object of the present inve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/88C07C231/14A01N47/34A01P13/00
Inventor 刘宇郝宝成梁剑平尚若峰王学红程富胜华兰英
Owner LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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