Sulfonylurea compound, preparation method thereof and use in preparing herbicide

A technology of compound and sulfonylurea, which is applied in the field of preparation of herbicides for the control of barnyardgrass, a malignant weed, can solve the problems of unselected safety and poor control effect of crops

Active Publication Date: 2020-01-03
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Since the advent of chlorsulfuron in the 1970s, there have been dozens of commercialized sulfonylurea herbicides targeting AHAS. Well, or the herbicides that are destructive are not safe for cro

Method used

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  • Sulfonylurea compound, preparation method thereof and use in preparing herbicide
  • Sulfonylurea compound, preparation method thereof and use in preparing herbicide
  • Sulfonylurea compound, preparation method thereof and use in preparing herbicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1. Preparation of compound FMO

[0022] Dissolve 8.65g (50mmol) of o-hydroxybenzenesulfonamide in 150mL of N,N-dimethylformamide, then add 34.5g (250mmol) of potassium carbonate, and stir the system at room temperature for 30 minutes. Then, 4.1 mL (50 mmol) of 1-fluoro-2-iodoethane was added dropwise to the reaction liquid, the temperature was raised to 100° C., and the reaction was refluxed overnight. Then filter and take the filtrate, add 300mL water and ethyl acetate (100mL×3) for extraction, dry the organic phase, and separate the product by column chromatography to obtain white to light yellow solid 2-(2-fluoroethoxy)benzenesulfonamide 3.7 g, yield 34%. of the intermediate 1 H NMR data is: (400MHz, CDCl 3 )δ7.94(dd, J=7.8,1.3Hz,1H,ArH),7.55(td,J=8.1,1.2Hz,1H,ArH),7.13(t,J=7.6Hz,1H,ArH),7.03 (d,J=8.3Hz,1H,ArH),5.11(s,2H,NH),4.89(ddd,J=47.2,4.9,3.0Hz,2H,CH 2 CH 2 F), 4.49–4.32 (m, 2H, CH 2 CH 2 F).

[0023] 7.0g (50mmol) of 2-amino-4-methoxyl-6-me...

Embodiment 2

[0029] Embodiment 2, compound are to the herbicidal effect of four kinds of model weeds on the pot test model

[0030] Liquid preparation

[0031] Preparation of emulsified water: first prepare a water emulsion with a content of 1‰, weigh 1g emulsifier with a beaker, add a small amount of distilled water to fully dissolve it, put it into a 1000mL volumetric flask, wash the beaker with distilled water several times, and pour it all into the volumetric flask , and finally add to the mark by distillation, shake well and set aside.

[0032] Mother liquor preparation: Weigh 30 mg of the test sample, add 1 mL of DMSO to fully dissolve it, and prepare a 30 mg / mL mother liquor. After calculating the dosage according to the spray area, pipette the required volume into a 10mL small beaker, and add the corresponding volume of emulsified water to make an aqueous emulsion for spraying. If necessary, serially dilute to obtain the desired aqueous emulsion for later use.

[0033] Spray equ...

Embodiment 3

[0040] Embodiment 3, the broad-spectrum herbicidal effect of compound to various weeds

[0041] The specific experimental details of the soil treatment method and the stem and leaf treatment method are the same as in Example 2. The compounds tested in the experiment are FMO, CMO, and the commercial herbicide trisulfuron-methyl, and the weed types are thrush, barnyardgrass, and amansia Wheat, goosegrass, foxtail, soda, echinacea, chrysanthemum, bittern, purslane, morning glory, velvetleaf, alfalfa, shepherd's, ashweed, dandelion, polygonum, and barnyardgrass at a dose of 1 g / mu. Table 3 shows the broad-spectrum herbicidal effects of the compounds.

[0042] Table 3, the broad-spectrum control effect of test compound on various weeds (1 gram / mu dose, percent inhibition rate)

[0043]

[0044]

[0045] * - Indicates that the herbicidal results under this condition were not measured due to insufficient crop seeds tested.

[0046] It can be seen from the table that FMO and ...

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PUM

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Abstract

The invention relates to a kind of sulfonylurea compound and its use in preparing herbicides. The compound has good control effects on rape, retroflexus amaranth, Echinochloa crusgalli(L.)Beauv, common crabgrass herb, eragrostis curvula, barnyard grass, bromus inermis, Eleusine indica, Setaria viridis, Puccinellia distans, Elymus dahuricus, Flaveria bidentis, Ixeris sonchifolia, purslane, morningglory, Abutilon theophrasti, alfalfa, water chestnut, Chenopodium album Linn, dandelion and Polygonum hydropiper, at a dose of 0.5-1g/mu. At a dose of 1g/mu, when stem and leaf treatment or soil treatment is performed, the herbicide has reasonable biological safety for soybean and peanut. These compounds can be used as herbicides in soybean and peanut fields, or broad-spectrum herbicides in non-crop fields such as forest farms or wasteland. The chemical structural formula of the sulfonylurea compound is as follows.

Description

technical field [0001] The invention belongs to the technical field of agrochemicals, and relates to a class of sulfonylurea compounds, a preparation method thereof and an application in the preparation of herbicides, in particular to an application in the preparation of herbicides for preventing and eliminating malignant weed barnyardgrass. [0002] technical background [0003] Acetolactate synthase (acetohydroxyacid synthase, AHAS, E.C.2.2.1.6) is the first key enzyme that plays a catalytic role in the biosynthesis pathway of leucine, valine and isoleucine. This biochemical process only exists in plants And in microorganisms, animals themselves cannot synthesize these branched-chain amino acids and need to obtain them from food to maintain life. Therefore, inhibitors targeting AHAS have natural biosafety for humans, animals and other mammals (McCourt JA, etal.Amino Acids, 2006, 31(2), 173-210). [0004] The crystal structure of AHAS-herbicide complexes from the model plan...

Claims

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Application Information

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IPC IPC(8): C07D239/47A01N47/36A01P13/00
CPCC07D239/47A01N47/36
Inventor 王建国李永红
Owner NANKAI UNIV
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