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A compound containing a benzotriazinone structure, its preparation method and application, and a herbicide

A benzotriazinone and compound technology, applied in the field of herbicides, can solve the problems of increasing the dosage of herbicides in wheat fields, increasing the control cost, exceeding the standard of pesticide residues, etc., and achieving excellent herbicidal activity, excellent HPPD inhibitory activity, and good safety. Effect

Active Publication Date: 2022-03-01
SHANDONG CYNDA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the resistant populations of major weeds such as Artemisia soprano, Shepherd's Purse, Aurantium japonica, Japanese kangaroo, brome, barley, and wild oats in wheat fields have developed into dominant weeds, resulting in the occurrence of The continuous increase in the use of herbicides in wheat fields not only increases the cost of control, but also leads to frequent incidents of pesticide damage and excessive pesticide residues; resistant weeds such as barnyardgrass and chinensis in rice fields have also reached the point where no medicine can be applied

Method used

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  • A compound containing a benzotriazinone structure, its preparation method and application, and a herbicide
  • A compound containing a benzotriazinone structure, its preparation method and application, and a herbicide
  • A compound containing a benzotriazinone structure, its preparation method and application, and a herbicide

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0085] Preparation Example 1: Preparation of Compound 1

[0086]

[0087] Add 75.5g of the compound shown in 1-1 to a 2L reaction flask at room temperature, add 1L of glacial acetic acid while stirring, then dissolve 88.5g of ICl into 300mL of glacial acetic acid, and add dropwise to the above reaction within 30min while stirring In the system, after the dropwise addition was completed, the stirring reaction was continued for about 3 hours. After the reaction was completed, the reaction solution was suction-filtered, and the obtained solid was washed with 500 mL of glacial acetic acid and dried to obtain Intermediate 1-2 with a yield of 98%.

[0088] Add 135g of intermediate 1-2 to a 2L flask, add 1L of tetrahydrofuran, then add 145.5g of triphosgene, then react overnight, wash with saturated sodium carbonate solution after the reaction, extract with ethyl acetate, combine the organic phases, anhydrous Drying over sodium sulfate and dehydration gave Intermediate 1-3 with a...

preparation example 2

[0096] Preparation Example 2: Preparation of Compound 50

[0097]

[0098] Add 5.7g of intermediate 1-5 into a 200mL single-neck flask, add 50mL of DMF, and add 7.2g of Cs under stirring 2 CO 3 The stirring reaction was continued for about 30 min. Then 3.7 g of benzyl bromide was slowly added dropwise into the reaction system, and after the dropwise addition was completed, the reaction was stirred at room temperature overnight. After the reaction was completed, 100 mL of water was added to the system, and the reaction system was extracted 3 times with 50 mL of ethyl acetate each time. The organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain intermediate 1-11 in a yield of 90%.

[0099] 6.8 g of Intermediate 1-11, 3.2 g of CuCN were added to a 200 mL two-neck flask, and 60 mL of dry DMF was added. The reaction was refluxed for 12 hours. After the reaction was completed, DMF was distilled off un...

preparation example 3

[0103] Preparation Example 3: Preparation of Compound 77

[0104]

[0105] Add 885 mg of intermediate 1-13 to a 50 mL single-necked bottle, add 15 mL of dry THF, and slowly add 714 mg 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 CH 2 Cl 2 , 378 mg of compound 1-9b, 606 mg of Et 3 N, 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 Drying and passing through the column gave intermediate 1-15 with a yield of 90%.

[0106] 1.1g of intermediate 1-15 was added to a 50mL two-necked bottle, 25mL of anhydrous acetonitrile was added, and N 2 Add 545 m...

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Abstract

The invention relates to the field of pesticide compounds, and discloses a compound containing a benzotriazinone structure, a preparation method and application thereof, and a herbicide. The compound has a structure represented by formula (I). The compounds containing the benzotriazinone structure provided by the present invention have excellent HPPD inhibitory activity, and are especially resistant to weeds in bulk crops such as rice and wheat and some important economic crops (such as peanuts, soybeans, cotton, etc.). Excellent herbicidal activity against sexual weeds and good safety profile on non-target crops.

Description

technical field [0001] The present invention relates to the field of pesticide compounds, in particular to a compound containing a benzotriazinone structure, a method for preparing the compound containing a benzotriazone structure, and the application of the compound as an HPPD inhibitor. Use in controlling weeds and a herbicide containing said compound. Background technique [0002] In today's world, a series of problems such as the reduction of available arable land, diseases, insect pests and weeds all hinder the sustainable development of modern agriculture. Among them, various types of weeds have become the number one problem affecting crop yield. [0003] Although there are various herbicides on the market for controlling weeds, the ensuing problem of herbicide resistance has far exceeded people's expectations. Taking my country as an example, more than 40 kinds of resistant weeds have been officially reported, and China is one of the five countries most seriously aff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D253/08C07D405/06C07D405/04C07D409/04C07D401/04C07D403/06C07D405/14A01N43/707A01P13/00
CPCC07D253/08C07D405/06C07D405/04C07D409/04C07D401/04C07D403/06C07D405/14A01N43/707
Inventor 杨光富严耀超曲仁渝吴微王现全陈恩昌张天柱杜晨
Owner SHANDONG CYNDA CHEM
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