Piperazinone derivatives, preparation method thereof, inhibitor, and method for preventing and controlling root parasitic weeds

The technology of a derivative, piperazinone, is applied in the field of pesticides, which can solve the problems of unstable ingredients and high cost of compounds, and achieve the effects of stable ingredients, low preparation costs, and inhibition of germination

Active Publication Date: 2019-08-20
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to provide piperazinone derivatives and preparation methods thereof, and inhibitors for inhibiting root parasitic weed strigold receptor proteins in order to overcome the problems of high compound cost and unstable components in the prior art , and methods for controlling root parasitic weeds

Method used

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  • Piperazinone derivatives, preparation method thereof, inhibitor, and method for preventing and controlling root parasitic weeds
  • Piperazinone derivatives, preparation method thereof, inhibitor, and method for preventing and controlling root parasitic weeds
  • Piperazinone derivatives, preparation method thereof, inhibitor, and method for preventing and controlling root parasitic weeds

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preparation example Construction

[0033] The second aspect of the present invention provides a method for preparing piperazinone derivatives, comprising the following steps:

[0034] (A) In the presence of the first solvent and reducing agent, the R 1 -CHO and tert-butoxycarbonylpiperazine carry out reductive amination reaction to obtain synthetic amine; wherein, R 1 is cyclohexenyl, norbornyl, norbornenyl or adamantyl;

[0035] (B) in the presence of a second solvent and an acid, subjecting the synthetic amine to a tert-butoxycarbonyl removal reaction to obtain an intermediate represented by formula (V), Formula (V);

[0036] (C) in the presence of a third solvent, a base and an optional condensing agent, subjecting the intermediate to a compound having a structure shown in formula (VI), formula (VII), formula (VIII) or formula (IX) condensation reaction, Formula (VI), Formula (VII), Formula (VIII), Formula (IX),

[0037] Wherein, Z is hydroxyl, chlorine atom or bromine atom; R 2 is methylene, met...

Embodiment 1

[0076] (A) Preparation of intermediate C: 1-(cyclohexane-3-en-1-ylmethyl)piperazine

[0077]

[0078] 3-cyclohexene-1-carbaldehyde (represented by A, 5g, 45.5mmol), tert-butoxycarbonylpiperazine (represented by B, 8.46g, 45.5mmol) and dichloromethane (150mL) were added to the reaction flask , and cooled to 0°C. Sodium triacetoxyborohydride (14.45 g, 68.2 mmol) was added under stirring, and after 30 min, the system was moved to room temperature and the reaction was stirred overnight. After the reaction was completed, water (100 mL) was added to the system and vigorously stirred for 15 min. Separate the organic layer, wash the aqueous layer with 50 mL of dichloromethane, combine the organic layers, wash the organic layer with water and saturated brine successively, dry with anhydrous sodium sulfate, remove the organic solvent under reduced pressure, and the obtained synthetic amine is not After separation, it was directly used in the next reaction, wherein the yield of the ...

Embodiment 2

[0087] (A) Preparation of intermediate C: 1-(cyclohexan-3-en-1-ylmethyl)piperazine. Prepared according to the method of Example 1.

[0088] (B) Preparation of Compound I-2: 1-(4-(3-cyclohexene-1-methylene)piperazin-1-yl)-2-(2,4-dichlorophenoxy)ethanone

[0089]

[0090] 1-(3-cyclohexene-1-methylene)piperazine (expressed as C, 0.2g, 1.11mmol), 2-(7-oxybenzotriazole)-N,N,N', N'-tetramethyluronium hexafluorophosphate (HATU, 0.55g, 1.44mmol), 2,4-dichlorophenoxyacetic acid (expressed as E, 0.25g, 1.11mmol) and dichloromethane (30mL) were added to in the reaction vial. N,N-Diisopropylethylamine (DIPEA, 0.287g, 2.22mmol) was added dropwise under stirring and the reaction was stirred at room temperature for 10h. After the reaction was completed, 20 mL of water was added to the system and vigorously stirred for 10 min. The organic layer was separated, the aqueous layer was extracted once again with 20mL of dichloromethane, the organic layers were combined, the organic layer was...

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Abstract

The invention relates to the field of pesticides, and discloses piperazinone derivatives, a preparation method thereof, an inhibitor, and a method for preventing and controlling root parasitic weeds.The piperazinone derivatives have a structure represented by a formula (I) shown in the description, wherein R<1> is cyclohexenyl, norbornyl, norbornenyl or adamantyl, R<0> is a group having a structure represented by a formula (II), a formula (III) or a formula (IV) shown in the description, R<2> is methylene, methine, difluoromethyl, amino or phenyl, R<3> is an oxygen atom, and R<4> is substituted or unsubstituted phenyl, substituted or unsubstituted p-(methylsulphonyl)tolyl, substituted or unsubstituted phenoxy, substituted or unsubstituted naphthyl, a substituted or unsubstituted group shown in the description, a substituted or unsubstituted group shown in the description, or substituted or unsubstituted pyridyl. The piperazinone derivatives provided by the invention have high stability, can efficiently inhibit activity of striga asiatica receptor proteins, and can inhibit germination of root parasitic weed seeds in the presence of strigolactone analogue GR24.

Description

technical field [0001] The present invention relates to the field of pesticides, in particular to piperazinone derivatives and a preparation method thereof, an inhibitor containing the above-mentioned piperazinone derivatives for inhibiting root parasitic weed strigold receptor proteins, and using the above-mentioned inhibitors for Methods of controlling root parasitic weeds. Background technique [0002] Striga and letang are root parasitic weeds, which parasitize the roots of crops, such as corn, sorghum, sunflower, melon, tomato and cereals, etc., absorb water and nutrients from the host roots, causing severe crop yield reduction, or even failure . Striga and Liedang are distributed all over the world, among which Striga is mainly distributed in subtropical and tropical regions, and Liedang is mainly distributed in subpolar and temperate regions. At present, there is no effective herbicide for controlling root parasitic weeds, and the annual economic loss caused by root...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/192C07D295/185C07D209/18C07D295/215A01N43/60A01P13/00
CPCC07D295/192C07D295/185C07D209/18C07D295/215A01N43/60
Inventor 席真王大伟庞智黎
Owner NANKAI UNIV
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