Quinazolinedione compound and applications thereof, and pesticide herbicide

A technology of quinazolinediones and compounds, which is applied in the field of pesticides and herbicides, can solve the problems of not providing the biological activity test results of compounds, etc., and achieve the effects of excellent crop safety, subsequent crop safety, and high safety

Active Publication Date: 2019-10-22
辽宁先达农业科学有限公司
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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

Method used

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  • Quinazolinedione compound and applications thereof, and pesticide herbicide
  • Quinazolinedione compound and applications thereof, and pesticide herbicide
  • Quinazolinedione compound and applications thereof, and pesticide herbicide

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0042] Preparation Example 1: Compound 1 was synthesized using the following synthetic route

[0043]

[0044] 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%.

[0045] 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 to the reaction sys...

preparation example 2

[0052] Preparation example 2: the preparation method of compound 2

[0053] Compound 1 (91.3mmol) was dissolved in THF (457ml), and triethylamine (182.7mmol), N,N-diethylformyl chloride (182.7mmol) and DMAP (27.4mmol) were added in sequence. Raise the temperature to reflux for 5 hours. After the reaction is completed, cool to return to room temperature, and stand at 0°C for 2 hours. The solid is removed by suction filtration. Methyl chloride was dissolved and the organic phase of dichloromethane was washed twice with water, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with diethyl ether, with a yield of 91%.

[0054] For the preparation methods of the compounds in the above reference samples, refer to the aforementioned Preparation Example 1 and Preparation Example 2.

[0055] The characterization data of the above-mentioned reference sample and the compound of the present invention are listed in Table 1 respectively:

[005...

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PUM

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Abstract

The present invention relates to the field of pesticide herbicides, and discloses a quinazolinedione compound and applications thereof, and a pesticide herbicide, wherein the quinazolinedione compoundhas a structure represented by a formula (I), and R is H or a group represented by a formula (I-1). According to the present invention, the quinazolinedione compound has excellent weeding activity and excellent crop safety.

Description

technical field [0001] The invention relates to the field of pesticides and herbicides, in particular to a quinazolinedione compound, the application of the quinazolinedione compound and a pesticide and herbicide containing the quinazolinedione compound. 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. Herbicides targeting HPP...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06A01N43/56A01N47/18A01P13/00
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 辽宁先达农业科学有限公司
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