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3-arylpyridazinone compound, preparation method, pesticide composition and use

A compound, pyridazinone technology, applied in the field of 3-arylpyridazinone compounds, can solve the problems of low herbicide activity, impact on subsequent crops, narrow herbicidal spectrum, etc.

Active Publication Date: 2020-03-10
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the low herbicidal activity of herbicides in the prior art, narrow herbicidal spectrum, poor crop safety, narrow application period, long soil residue period, serious impact on subsequent crops, ecological toxicity and environmental problems. 3-aryl pyridazinone compounds, preparation method, pesticide composition and use are provided due to defects such as poor compatibility

Method used

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  • 3-arylpyridazinone compound, preparation method, pesticide composition and use
  • 3-arylpyridazinone compound, preparation method, pesticide composition and use
  • 3-arylpyridazinone compound, preparation method, pesticide composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0151] intermediate synthesis

[0152] Synthesis of 3-chloro-1-methyl-6-trifluoromethylpyridazin-4(1H)-one

[0153]

[0154] 300g (3.04mol, 1eq.) of maleic anhydride was suspended in 900mL of carbon tetrachloride, and then 513g (3.2mol, 1.05eq.) of liquid bromine was slowly added dropwise under light, and after the addition of liquid bromine was completed, the reaction was 32 -40h, proton nuclear magnetic spectrum tracking reaction process. After the reaction was completed, the solvent carbon tetrachloride and excess liquid bromine were distilled off under reduced pressure to obtain 750 g of light yellow solid 2,3-dibromosuccinic anhydride 2 with a yield of 95%.

[0155] 1 H-NMR (300MHz, CDCl 3 ):δ4.88(s,2H)

[0156] Weigh 300g (1.16mol, 1eq.) of compound 2 in a 2L three-neck flask, add 500mL of glacial acetic acid at room temperature to dissolve 2, slowly add 105g (1.28mol, 1.1eq.) of anhydrous sodium acetate, and reflux for 5h. After the reaction was completed, the r...

Embodiment 2

[0171] FQ-71

[0172]

[0173] 2.9g (73.2mmol, 1.2eq.) of sodium hydroxide was dissolved in 200ml of water, and 10.0g (61mmol, 1.0eq.) of compound 1-2 was added in batches to aqueous sodium hydroxide solution. 6.9g (73.2mmol, 1.2eq.) of methyl chloroformate, after dropping, warmed up to room temperature and reacted for 3 hours. After the reaction was complete, it was suction filtered, and the filter cake was dried to obtain 12.7 g of white solid 2-2, with a yield of 93.7%.

[0174] 10.0g (45.2mmol, 1.0eq.) of compound 2-2 was dissolved in 40ml of 98% concentrated sulfuric acid, cooled to 0°C in an ice-water bath, and 3.0g (47.4mmol, 1.05eq.) of 65% concentrated nitric acid was added dropwise. React for 5 hours. After the reaction was complete, the reaction solution was slowly poured into ice water, a yellow solid precipitated out, filtered with suction, and the filter cake was dried to obtain 9.2 g of yellow solid 3-2 with a yield of 76.4%.

[0175] 10.0g (37.6mmol, 1.0e...

Embodiment 3

[0182] FQ-67

[0183]

[0184] 339mg (1.0mmol, 1.0eq.) Compound FQ-71 was dissolved in 40ml of acetonitrile, 207mg (1.5mmol, 1.5eq.) of potassium carbonate was added, 255mg (1.5mmol, 1.5eq.) of iodoisopropane was added, and the reaction was carried out at 50°C 4 hours. After the reaction was complete, cool, filter with suction, and spin dry the filtrate to obtain a crude product, which was purified by column chromatography to obtain 320 mg of FQ-67 with a yield of 83.9%.

[0185] Solid, m.p.: 99-100°C; HPLC: 99.4%; 1 H-NMR (300MHz, CDCl 3 ):δ7.49(s,1H),6.99(d,2H),4.43-4.60(m,1H),4.08(s,3H),1.38(d,6H); 19 F-NMR (282MHz, CDCl 3 ):δ-70.64(s,3F); MS(ESI):m / z 380(M + ),403(M+Na) +

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PUM

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Abstract

Provided are 3-aryl pyridazinone as shown by formula I, and a preparation method, pesticide composition and use. The 3-aryl pyridazinone provided has a highly-efficient herbicidal activity, a relatively broad phytocidal range, good crop safety, a relatively wide drug application period, and a short residual life in the soil; the 3-aryl pyridazinone exhibits good pre-emergence and post-emergence herbicidal activity at low doses, has control effects on all of farmland broadleaved weeds, farmland gramineae weeds and Cyperaceae weeds, and has a certain safety for crops such as corn, rice, wheat, cotton and soybeans at high doses; the 3-aryl pyridazinone can effectively inhibit the germination of weeds, and at the same time has a good herbicidal activity on 3-6 leaf-stage sensitive large weeds and no harmful effects on the growth of succeeding crops; and the 3-aryl pyridazinone has a reasonable toxicity, ecotoxicity and environmental capability, belonging to environmentally friendly low-toxic pesticides with good market prospects.

Description

technical field [0001] The invention relates to 3-aryl pyridazinone compounds, a preparation method, a pesticide composition and use. Background technique [0002] Protoporphyrinogen oxidase is the target of many types of herbicides, such as diphenyl ether, N-phthalimide, oxadiazole, phenylpyrazole, oxazolidinedione, triazolone, imine, pyrimidinedione etc. Since the protoporphyrinogen oxidase inhibitor herbicide uses the chlorophyll of plant cells as the point of action, it ensures the selective toxicity between animals and plants, and has the characteristics of ultra-high efficiency, low toxicity, and no cross-resistance. This type of herbicide has Good prospects for development. Kixor (saflufenacil, saflufenacil), launched by BASF in recent years, can effectively control more than 70 kinds of weeds in corn, sorghum, soybean, small grains, cotton, fruit trees and nuts, and is safe for crops. In 2009, it was authorized to be registered in Argentina, Chile, Nicaragua and t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D237/14C07D417/04C07D413/04C07F5/02A01N43/58A01N43/76A01N43/78A01N43/84A01P13/00
CPCA01N43/58A01N43/76A01N43/78A01N43/84C07D237/14C07D413/04C07D417/04C07F5/025
Inventor 吕龙吕强唐庆红付群梅张基胜刘世梦戴明张志国沈娟芦昕婷
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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