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A kind of quinazoline dione compound containing unsaturated group and its application and a kind of pesticide herbicide

A quinazolinedione and compound technology, which is applied in the field of pesticides and herbicides, can solve the problems of not providing the biological activity test results of the compounds, not being able to directly use the control of weeds in paddy fields, and not showing sufficient safety, etc.

Active Publication Date: 2020-09-04
SHANDONG CYNDA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Subsequently, WO2017 / 140612A1 further disclosed a series of HPPD inhibitor molecules on this basis, however, the biological activity test results of specific compounds were not provided in this prior art
Moreover, it has been confirmed by experiments that the compounds specifically recorded in the prior art do not show sufficient safety to crops such as rice and wheat, so they cannot be directly used in paddy fields for the control of weeds

Method used

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  • A kind of quinazoline dione compound containing unsaturated group and its application and a kind of pesticide herbicide
  • A kind of quinazoline dione compound containing unsaturated group and its application and a kind of pesticide herbicide
  • A kind of quinazoline dione compound containing unsaturated group and its application and a kind of pesticide herbicide

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0194] Preparation Example 1: The raw material compound 8a was synthesized using the following synthetic route

[0195]

[0196] Preparation of compound 2a: Dissolve 2-methyl-6-aminobenzoic acid (i.e., compound 1a) (100mmol) in acetic acid (1200ml), add 1mol / L ICl acetic acid solution dropwise under stirring, and continue stirring after the addition is complete Reaction 2h. A large amount of solids will be precipitated during the reaction, and TLC will track the reaction process, after the reaction is completed. The filtrate was removed by suction filtration under reduced pressure, the obtained solid was washed twice with 500 mL of acetic acid, and after drying, an off-white solid was obtained with a yield of 93%.

[0197] Preparation of compound 3a: under nitrogen protection, compound 2a (20 mmol) and 30 ml of pyridine were added into a 100 mL two-necked bottle. After stirring until the solid was completely dissolved, m-chlorophenylisocyanate (25 mmol) was slowly added t...

preparation example 2

[0204] Preparation Example 2: Preparation of Compound 1 and Compound 2

[0205] Compound 8a (1.2mmol) was dissolved in acetonitrile, followed by adding K 2 CO 3 (1.44mmol), 3-bromopropyne (or 3-bromopropynene) (2.4mmol). Raise the temperature to 60°C and react overnight. After the reaction was completed, after cooling to return to room temperature, the solid was removed by suction filtration, and the filtrate was collected and subjected to column chromatography for separation and purification to obtain the final product.

preparation example 3

[0206] Preparation Example 3: Preparation of Compound 3

[0207]

[0208] Add 10mmol of compound 3a into a 50mL single-necked bottle, add 18mL of dry THF, and slowly add 15mmol of SOCl dropwise at room temperature 2 , After the dropwise addition was completed, the reaction was refluxed at 75°C for about 1.5h, and the reaction progress was tracked by TLC, and the solvent was removed after the reaction. Add 20 mL of dry CHCl 3 , 15 mmol of 2,5-dimethyl-2,4-dihydro-3H-pyrazol-3-one, 15 mmol of Et 3 N, reacted for about 0.5h, followed by TLC until the acid chloride disappeared. After the reaction was completed, wash with 20 mL of water once, CH 2 Cl 2 Extraction, wash twice with 10 mL of 1 mol / L HCl each time, wash with 10 mL of saturated NaHCO each time 3 Wash 2 times, anhydrous Na 2 SO 4 After drying, pass through the column to obtain compound 3b.

[0209] Add 5mmol of compound 3b into a 50mL two-necked bottle, add 28mL of anhydrous acetonitrile, N 2 Add 10mmol of Et...

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Abstract

The invention relates to the field of pesticides and herbicides, and discloses a quinazolinedione compound containing an unsaturated group and its application and a pesticide herbicide. The quinazolinediones compound containing an unsaturated group of the present invention has The structure shown in formula (I). The unsaturated group-containing quinazolinedione compound provided by the invention has good control effect and excellent safety.

Description

technical field [0001] The present invention relates to the field of pesticide herbicides, in particular to an unsaturated group-containing quinazolinediones compound and the application of the unsaturated group-containing quinazolinediones compound and a compound containing the unsaturated group Pesticide herbicides of the class of quinazolinediones. 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 nor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06A01N43/54A01P13/00
CPCC07D403/06A01N43/54A01N47/18A01N43/56C07D405/14A01N43/80A01N43/60A01N43/84A01N57/16C07D401/14C07D403/14C07D409/14C07D413/14C07F9/6558C07H1/00C07H17/02
Inventor 杨光富曲仁渝何波南甲戌严耀超王现全
Owner SHANDONG CYNDA CHEM
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