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Triketone compound containing quinazolinedione fragment, preparation method and application of triketone compound, and herbicide

A technology of quinazoline diones and compounds, applied in the field of herbicides of triketones, capable of solving problems such as the lack of HPPD-inhibiting herbicides

Active Publication Date: 2020-04-07
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
[0008] Further, in view of the fact that there is no HPPD herbicide that can effectively control gramineous weeds such as brome, wild oats, and barley that seriously endangers the growth of wheat in my country's agricultural production; and for the cash crop peanut, there is still a lack of usable HPPD-inhibiting herbicides are used to control grassy weeds such as barnyardgrass, crabgrass, and foxtail in peanut fields

Method used

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  • Triketone compound containing quinazolinedione fragment, preparation method and application of triketone compound, and herbicide
  • Triketone compound containing quinazolinedione fragment, preparation method and application of triketone compound, and herbicide
  • Triketone compound containing quinazolinedione fragment, preparation method and application of triketone compound, and herbicide

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preparation example Construction

[0129] According to the method for preparing the triketone compound of the structure shown in the 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 in the base according to the conventional conditions and operation of the rearrangement reaction. Contact is carried out in the presence of a solvent.

[0130] 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).

[0131] 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.

[0132] It should be understood by those skilled in the art that the method...

preparation example

[0152] Preparation example (X is OH, Y is methyl)

[0153]

[0154] Add 50mmol of the compound shown in 1-1 into a 250mL reaction flask at room temperature, add 100mL of glacial acetic acid while stirring, then dissolve 50mmol of ICl into 30mL of glacial acetic acid, and add dropwise to the above reaction system within 15min while stirring , After the dropwise addition, continue to stir the reaction 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).

[0155] 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 while sti...

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Abstract

The invention relates to the field of pesticides and herbicides, and discloses a triketone compound containing a quinazolinedione fragment, a preparation method and an application of the triketone compound, and a herbicide; the triketone compound has a structure represented by a formula (I). The triketone compound containing the quinazolinedione fragment and provided by the invention can be used as a broad-spectrum HPPD herbicide for preventing and killing gramineous weeds; in addition, the triketone compound containing the quinazolinedione fragment and provided by the invention has a good control effect on barnyard grass, green bristlegrass, crab grass, brome, wild oat, aegilops tauschii, alopecurus aequalis, alopecurus japonicus and other gramineous weeds which are difficult to control.

Description

technical field [0001] The present invention relates to the field of pesticide herbicides, in particular to a triketone compound containing a quinazolinedione fragment, a preparation method and application thereof, and a herbicide containing the triketone compound containing a quinazolinedione fragment agent. Background technique [0002] 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 among all targeted herbicides and One of the slowest developing herbicides and has no cross-resistance with other types of herbicides. It can be see...

Claims

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Application Information

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IPC IPC(8): C07D239/96C07F7/08C07D405/04C07D405/06A01N43/54A01N55/10A01P13/00
CPCC07D239/96C07F7/0812C07D405/04C07D405/06A01N43/54A01N55/00Y02P20/55
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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