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Pyridinooxazone-pyridinopyrimidone compounds and preparation method and application thereof

The technology of a compound and oxazinone, which is applied in the application field of weed control, can solve problems such as bio-ecological safety problems, and achieve the effects of good herbicidal activity, novel structure, and growth inhibition.

Inactive Publication Date: 2014-04-02
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the long-term use of some herbicide varieties, the problem of weed resistance to herbicides has also become prominent, and increasing the amount of use for this will also lead to problems in biological ecological safety

Method used

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  • Pyridinooxazone-pyridinopyrimidone compounds and preparation method and application thereof
  • Pyridinooxazone-pyridinopyrimidone compounds and preparation method and application thereof
  • Pyridinooxazone-pyridinopyrimidone compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of various phenoxyacetyl chlorides (Formula 4)

[0034]

[0035] The phenoxyacetyl chloride (formula 4) in the present invention is prepared from the corresponding substituted phenoxyacetic acid by a conventional acid chloride method. The general method of its synthesis is as follows: Dissolve phosphorus pentachloride in dichloromethane, add substituted phenoxyacetic acid under ice bath, heat and reflux reaction in oil bath for 10h, until no gas is released, remove dichloromethane by normal pressure distillation, and distill under reduced pressure Phosphorus oxychloride is removed to obtain a brownish-yellow liquid, which is substituted phenoxyacetyl chloride (Formula 4).

Embodiment 2

[0037] Preparation of 2-(2,4-dichlorophenoxymethyl)-4H-pyridin[2,3-d][1,3]oxazin-4-one (EQN1)

[0038]

[0039] Dissolve 2-aminonicotinic acid (3a, 0.3g, 2.2mmol) in 10mL DMF solution, add dropwise 2,4-dichlorophenoxyacetyl chloride (4a, 0.35mL, 2.2mmol) under ice-cooling, add Triethylamine (0.32mL, 2.2mmol), continue to react at room temperature for 12h. Filtered, washed with saturated saline and sodium bicarbonate solution successively, the organic layer was dried over anhydrous sodium sulfate, and then silica gel column chromatography was obtained to obtain light yellow solid 2-(2,4-dichlorophenoxymethyl)-4H-pyridine [2,3-d][1,3]oxazin-4-one (EQN1), yield 75%, m.p.198.8-199.6°C.

[0040] 1 H NMR(600MHz,DMSO-d6):δ9.03(d,J=3.0Hz,1H),8.56(d,J=7.2Hz,1H),7.56(q,J=7.2Hz,1H),7.40( s,1H),7.18(d,J=6.6Hz,1H),7.05(d,J=8.4Hz,1H),5.10(s,2H).EI-MSm / z,(%):321.93(M + ,1.03),286.96(100.00).

Embodiment 3

[0042] Preparation of 2-(4-chlorophenoxymethyl)-4H-pyridin[2,3-d][1,3]oxazin-4-one (EQN2)

[0043]

[0044] The compound 2-(4-chlorophenoxymethyl)-4H-pyridin[2,3-d][1,3]oxazin-4-one (EQN2) was obtained by a synthetic method similar to Example 2, light yellow Solid, yield 70%, m.p.184.5-185.5°C.

[0045] 1 H NMR (400MHz, CDCl 3 ):δ9.03(d,J=2.8Hz,H),8.55(d,J=6.4Hz,H),7.56( q,J=3.2Hz,H),7.25(d,J=2.0Hz,2H),7.01(d,J=2.4Hz,2H),5.07(s,2H).EI-MS m / z,(%) :287.98(M + ,47.98), 146.93(100.00).

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Abstract

The invention discloses pyridinooxazone-pyridinopyrimidone compounds and a preparation method and an application thereof. The pyridinooxazone-pyridinopyrimidone compounds have the following structures shown in formulae 1 and 2: R1 is hydrogen or chlorine; R2 is hydrogen, chlorine or fluorine; R3 is hydrogen, amido, methyl or carboxymethyl; X, Y and Z are nitrogen or hydrocarbon. The synthetic line comprises the following steps: dissolving amino substituted picolinic acid in an organic solvent; in the presence of organic alkali, carrying out reaction with substituted phenoxyacetyl chloride to obtain the pyridinooxazone compounds; and reacting the pyridinooxazone compounds with substituted amine in an organic solvent to obtain the pyridinopyrimidone compounds. The pyridinooxazone-pyridinopyrimidone compounds are used for preventing and treating weed. Part of the pyridinooxazone and pyridinopyrimidone compounds has high herbicidal activity and can effectively inhibit growth of dicotyledon.

Description

technical field [0001] The invention relates to a pyridoxazinone compound and a pyridopyrimidinone compound, a preparation method thereof, and an application of the two compounds in controlling weeds. Background technique [0002] Weeds are one of the main hazards in crop production, and the use of herbicides to control the growth of weeds plays an important role in modern agricultural production. The growth of weeds consumes nutrients in the soil, blocks sunlight, and hinders the growth of crops; some weeds will release inhibitory factors, or accommodate pathogens that are harmful to crops, reducing the yield or economic value of surrounding crops. The development of herbicides in the world has gone from high-dose, broad-spectrum herbicides to today's ultra-low-dose, selective herbicides. The development of herbicides in the world is of great significance to improving agricultural productivity, ensuring biosafety, and protecting the ecological environment. [0003] There ...

Claims

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Application Information

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IPC IPC(8): C07D498/04C07D471/04A01N43/90A01P13/00
CPCC07D498/04A01N43/90C07D471/04
Inventor 涂海洋高建宏戴舒翔张爱东
Owner HUAZHONG NORMAL UNIV
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