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Acetolactate synthetase AHAS restrainer combination

A technology of acetolactate and composition, applied in the field of small molecule inhibitors

Inactive Publication Date: 2008-08-20
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there has never been any literature reporting that such compounds have AHAS inhibitory effects and herbicidal activity

Method used

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  • Acetolactate synthetase AHAS restrainer combination
  • Acetolactate synthetase AHAS restrainer combination
  • Acetolactate synthetase AHAS restrainer combination

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: the preparation of 5-chloro-indole-2,3-dione

[0021]

[0022] Add 4.0ml (40mmol) of chloral hydrate and 45.9g (324mmol) of anhydrous sodium sulfate to 120mL of water, raise the internal temperature to 40°C, stir until clear, and prepare the prepared aqueous solution of p-chloroaniline hydrochloric acid [p-chloroaniline 4.59g ( 36.0mmol) dissolved in 54mL 2.5% hydrochloric acid] was added dropwise to the reaction solution, and the addition was completed in 10-15 minutes. The reaction was continued for 0.5h, and a large amount of white precipitate was precipitated. At this time, 7.5g (108mmol) of hydroxylamine hydrochloride was quickly added, and the temperature was raised to 75°C , reacted for 4 hours, cooled to room temperature, suction filtered, and dried to obtain 6.78 g of khaki-colored 4-chloro-1-isonitroso-acetanilide (A) powder, with a yield of 95%.

[0023] Preheat 40ml of concentrated sulfuric acid to 75°C, add 6.00g (30mmol) of 4-chloro-1-ison...

Embodiment 2

[0025] Example 2: Inhibition of AHAS enzymes

[0026] The Arabidopsis AHAS gene (pET-ATAHAS: T86-CHis) was overexpressed in Escherichia coli (BL21(DE3)), and pure AHAS was obtained after IMAC purification by immobilized metal affinity chromatography (Chang A.K., et al.Biochem.J. , 327, 161-169). When measuring the activity, the pH value of the reaction solution is 7.0, the volume is 250 μL, and contains 50 mM Na 2 HPO 4 / NaH 2 PO 4Buffer system, 50mM sodium pyruvate, 10mM magnesium chloride, 1mM thiamine diphosphate (ThDP), 10μM flavin adenine dinucleotide (FAD), 100μg / mL test compound, react at 37°C Initiate for 30 min, add 25 μL of 10% HO 2 SO 4 Stop responding. Heat the system at 60°C for 15 min to convert all the acetolactate generated into 3-hydroxy-2-butanone, then add 250 μL of 0.5% creatine and 250 μL of 5% α-naphthol (in 4M NaOH), in Reheat at 60°C for 15 minutes, cool for 15 minutes, read the absorbance at 525nM, and calculate the inhibition of chlorine with ...

Embodiment 3

[0027] Example 3: Inhibition of Rapeseed Root Length

[0028] The test target is rapeseed (Brassica napus). Spread a piece of filter paper with a diameter of 5.6 cm in a petri dish with a diameter of 6 cm, add 2 ml of a 100 μg / mL or 10 μg / mL solution of the test compound (Table 1), repeat each concentration twice, and set clear water as a control. Sow 15 rapeseeds soaked for 4-6 hours, and measure the length of the embryo after culturing in the dark at 30±1°C for 48 hours. Compared with the blank control, the percentage inhibition was calculated. Summarized in Table 1. Table 1 shows the molecular structure and in vivo and in vitro biological activity test results of the series of compounds.

[0029] Table 1 Biological activity data of a series of compounds

[0030]

[0031]

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Abstract

The invention relates to an inhibitor compound for acetolactate synthetase AHAS, which is indoline diketone compound (I); wherein, R1 is H or CH3, R2 is O or N-OH, R3 is F, Cl, Br, I, CH3, OCH3, NO2, SO3H, OCF3 or CF3, R4 is F, Cl, Br, I, CH3 or OCH3. The inhibitor compounds for acetolactate synthetase has the advantages of having herbicidal activity, having inhibiting action upon arabidopis thaliana aceto-lactic acidsynzymeas well as upon growth of rape root and being used for designing new environmentally friendly herbicide molecule.

Description

technical field [0001] The present invention relates to a new class of small-molecule inhibitors mainly based on indolinediones with acetolactate synthase AHAS as the target, and specifically relates to the effect of this type of compound on Arabidopsis thaliana (Arabidopsis thaliana) in vitro. ) inhibitory activity of AHAS, and the inhibitory activity of these compounds on rapeseed root growth in vivo (in vivo). technical background [0002] Since entering the 21st century, food and environmental issues facing mankind have become increasingly prominent. On the one hand, the total population of the world continues to grow, and the global food supply is becoming more and more tense; on the other hand, the serious problems caused by chemical pollution in the natural environment on which human beings depend have also become a problem that cannot be ignored. Therefore, it has become an urgent historical task to ensure the maximum food supply while minimizing the negative impact...

Claims

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Application Information

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IPC IPC(8): A01N43/38A01P13/00
Inventor 王建国李正名李永红谭海忠
Owner NANKAI UNIV
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