Cyclohexanetrione compound, preparation method and application thereof, and herbicide

A technology of cyclohexatrione and compounds, applied in the field of cyclohexatrione compounds and their preparation, herbicides containing the cyclohexatrione compounds, to achieve good control effect

Active Publication Date: 2021-03-23
SHANDONG CYNDA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, nearly 20 kinds of commercialized HPPD herbicides that have been developed so far still have certain limitations. HPPD herbicide for millet, peanut, soybean and other crops
Further, in view of the actual agricultural production in my country, there is no HPPD herbicide that can effectively control gramineous weeds such as brome, wild oat, and barley, which seriously damage the growth of wheat.

Method used

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  • Cyclohexanetrione compound, preparation method and application thereof, and herbicide
  • Cyclohexanetrione compound, preparation method and application thereof, and herbicide
  • Cyclohexanetrione compound, preparation method and application thereof, and herbicide

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preparation example Construction

[0050] According to the method for the cyclohexanetrione compound of the structure shown in the preparation formula (I) of the present invention, those skilled in the art can mix the compound of the structure shown in the formula (II) and the catalyst according to the conventional conditions and operation of the rearrangement reaction The contacting is carried out in the presence of a base and a solvent.

[0051] Preferably, the molar ratio of the compound of the structure shown in the formula (II) to the catalyst and the base is 1: (0.01-1): (0.5-4); more preferably, the compound of the structure shown in the formula (II) and the catalyst The molar ratio to base is 1:(0.05-1):(1-3).

[0052] Preferably, the contact conditions include: the reaction temperature is 0-100°C; the reaction time is 0.5-24h; more preferably, the contact conditions include: the reaction temperature is 20-40°C; the reaction time is 5- 12h.

[0053] It should be understood by those skilled in the art ...

preparation example

[0074] Preparation example (Y is methyl)

[0075]

[0076] Add 50mmol of the compound shown in 1-1 into a 100mL reaction flask at room temperature, add 100mL of glacial acetic acid (dosage 1mmol = 2mL) while stirring, then dissolve 50mmol of ICl into 10mL of glacial acetic acid, drop it within 15min while stirring Add it to the above reaction system, after the dropwise addition, continue to stir and react for about 2.5h. After the reaction was completed, the reaction solution was suction-filtered under reduced pressure, and the obtained solid was washed with 100 mL of acetonitrile and 100 mL of glacial acetic acid, respectively, and dried to obtain Intermediate 1-2, melting point: 186-188°C. 1 H NMR (600MHz, DMSO-d 6): δ8.97 (brs, 3H), 7.72 (d, J = 8.4Hz, 1H), 6.75 (d, J = 7.8Hz, 1H), 2.40 (s, 3H).

[0077] Add 10mmol of intermediate 1-2 into a 100mL two-neck flask, add 36mL of pyridine, and slowly add 11mmol of the substituted isocyanate shown in 1-3 into the system whil...

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Abstract

The invention relates to the field of pesticide herbicides, and discloses a cyclohexanetrione compound and a preparation method and an application thereof, and a herbicide; the compound has a structure represented by a formula (I). The cyclohexanetrione compound provided by the invention can be used as an HPPD herbicide for controlling and killing gramineous weeds, and has a good control effect onbrome, wild oat, aegilops tauschii, alopecurus amurensis, alopecurus japonicus and other gramineous weeds which are difficult to control.

Description

technical field [0001] The invention relates to the field of pesticide herbicides, in particular to a cyclohexanetrione compound, its preparation method and application, and a herbicide containing the cyclohexanetrione compound. Background technique [0002] The explosive growth of weed resistance has become a key challenge for the sustainable development of modern agriculture, and the creation of new ultra-efficient herbicides is the fundamental way to solve this challenge. [0003] In research and practical field application in recent years, it has been found that herbicides inhibiting p-hydroxyphenylpyruvate dioxygenase (HPPD) have the characteristics of low toxicity and side effects, and environmental friendliness. More importantly, compared with AHAS, ACCase , PSII herbicides are extremely serious and exponentially increasing weed resistance problem, but there are few reports of resistance to HPPD-inhibiting herbicides, and its resistance problem is the least serious am...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D403/04C07D239/96C07D405/04C07D413/04C07D417/04A01N43/54A01N43/58A01N43/76A01N43/78A01N43/56A01N43/84A01N43/836A01N43/824A01N43/828A01P13/00
CPCA01N43/54A01N43/56A01N43/58A01N43/76A01N43/78A01N43/82A01N43/84C07D239/96C07D401/04C07D403/04C07D405/04C07D413/04C07D417/04
Inventor 杨光富曲仁渝严耀超南甲戌王现全陈恩昌张天柱杜晨
Owner SHANDONG CYNDA CHEM
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