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Pyrazole-based derivative containing quinazolinedione fragment, and applications thereof, and pesticide herbicide

A technology of quinazolinediones and pyrazoles, which is applied in the direction of sugar derivatives, sugar derivatives, biocides, etc., can solve the problems of loss of control effect and weed resistance of malignant weeds, and achieve good crops Safety, excellent prevention effect, good safety effect

Pending Publication Date: 2019-10-22
SHANDONG CYNDA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] During the use of pesticides and herbicides, due to the repeated overuse of a single type of herbicide and the mutation of the weed's own genes, the weeds have serious drug resistance
For example, ACCase and AHAS herbicides, due to the serious resistance of weeds in the field, even if the dosage of these herbicides is increased, they have lost the control effect on some malignant weeds

Method used

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  • Pyrazole-based derivative containing quinazolinedione fragment, and applications thereof, and pesticide herbicide
  • Pyrazole-based derivative containing quinazolinedione fragment, and applications thereof, and pesticide herbicide
  • Pyrazole-based derivative containing quinazolinedione fragment, and applications thereof, and pesticide herbicide

Examples

Experimental program
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Effect test

preparation example 1

[0055] Preparation Example 1: Synthesis of Compound 1-3a

[0056]

[0057] Add intermediate I-1a (5mmol) to a 50mL single-necked bottle, add 18mL dry THF, and slowly add SOCl dropwise at room temperature 2 (8mmol), after the dropwise addition, reflux at 75°C for about 1.5h, follow the reaction progress by TLC, and remove the solvent after the reaction. Add 20 mL of dry CHCl 3 , 1,3-Dimethyl-5-pyrazolone (6mmol), Et 3 N (10mmol), reacted for about 0.5h, followed by TLC until the acid chloride disappeared. After the reaction is completed, wash once with 20 mL of water, wash twice with 10 mL of 1 mol / L HCl each time, and wash twice with 10 mL of saturated NaHCO each time. 3 Wash 2 times, anhydrous Na 2 SO 4 Dry and pass through the column to obtain intermediate I-2b.

[0058] Intermediate I-2b (1mmol) was added to a 50mL two-necked bottle, 28mL of anhydrous acetonitrile was added, and N 2 Join Et under protection 3 N (2 mmol), acetone cyanohydrin (0.1 mmol). The react...

preparation example 2

[0059] Preparation Example 2: Synthesis of Compound 8

[0060] At 0°C, dissolve compound I-3a (1.5mmol) in anhydrous dichloromethane, add triethylamine (3mmol), stir and dissolve, then add cyclopropylformyl chloride (2mmol) to the reaction system, continue Stir for 3-6h. After the reaction was completed, a saturated sodium bicarbonate solution (15 ml) was slowly added to the reaction system, the reaction solution was extracted with dichloromethane, and the organic phase was washed twice with saturated brine. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product, which was then separated and purified by column chromatography.

preparation example 3

[0061] Preparation Example 3: Synthesis of Compound 46

[0062] At 0 °C, intermediate I-3a (1 mmol) was dissolved in ultra-dry DCM, and Et 3 N (1.5mmol) was stirred for 15min, and a solution of 2-thiophenesulfonyl chloride (1.5mmol) was slowly added dropwise to the reaction system, stirring was continued at 0°C for 30min, and then returned to room temperature for 3h. After the reaction was completed, a saturated sodium bicarbonate solution (15 ml) was added to the reaction system to separate and collect the organic phase, which was washed twice with saturated brine. The organic phase was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product, which was then separated and purified by column chromatography.

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Abstract

The present invention relates to the field of pesticide herbicides, and discloses a pyrazole-based derivative containing a quinazolinedione fragment, and applications thereof, and a pesticide herbicide, wherein the pyrazole-based derivative has a structure represented by a formula (I). According to the present invention, the pyrazole-based derivative has advantages of broad herbicidal spectrum andhigh safety to crops.

Description

technical field [0001] The invention relates to the field of pesticides and herbicides, in particular to a pyrazole derivative containing a quinazolinedione fragment, an application of the pyrazole derivative, and a pesticide and herbicide containing the pyrazole derivative. Background technique [0002] 4-Hydroxyphenylpyruvate dioxygenase (4-HPPD) was identified as the target of herbicides in the 1990s. [0003] 4-HPPD widely exists in aerobic organisms, and it is mainly involved in the metabolism of tyrosine in organisms. In plants, the metabolite of tyrosine, p-hydroxyphenylpyruvate, generates homogentisic acid under the action of 4-HPPD, and homogentisic acid is further converted into plastoquinone and tocopherol. Plastoquinone and tocopherol are important precursors for plant photosynthesis. Therefore, by inhibiting the synthesis of plastoquinone and tocopherol in plants, it hinders the normal photosynthesis of plants, causing albino symptoms and death of plants. [...

Claims

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Application Information

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IPC IPC(8): C07D403/06C07F9/6558C07D403/14C07D409/14C07H17/02C07H1/00C07D401/14C07D405/14C07D413/14A01N47/18A01N57/16A01N43/84A01N43/56A01N43/60A01N43/80A01P13/00
CPCC07D403/06A01N43/54A01N47/18A01N43/56C07D405/14A01N43/80A01N43/60A01N43/84A01N57/16C07D401/14C07D403/14C07D409/14C07D413/14C07F9/6558C07H1/00C07H17/02
Inventor 杨光富何波王现全
Owner SHANDONG CYNDA CHEM
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