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Dehydrozingerone derivative and preparation method and application thereof

A technology of dehydrozingerone and derivatives, applied in the field of pesticides, can solve the problem of less dehydrozingerone and achieve excellent broad-spectrum antifungal activity

Active Publication Date: 2019-11-05
HAINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, there are few reports on the use of dehydrozingerone as an insecticide and / or fungicide

Method used

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  • Dehydrozingerone derivative and preparation method and application thereof
  • Dehydrozingerone derivative and preparation method and application thereof
  • Dehydrozingerone derivative and preparation method and application thereof

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preparation example Construction

[0048] The present invention also provides a kind of preparation method of above-mentioned dehydrozingerone derivative, comprising:

[0049] The substituted benzaldehyde shown in formula (1) is reacted with the substituted acetone shown in formula (2) to obtain dehydrozingerone derivatives shown in formula (I).

[0050]

[0051] Among them, R 1 ~R 5 each independently selected from hydrogen, halogen, nitro, alkyl, substituted alkyl, alkoxy or hydroxyl; the substituents in the substituted alkyl are selected from one or more of halogen, nitro and hydroxyl;

[0052] R 8 selected from alkyl, alkoxy or substituted alkyl; the substituent in the substituted alkyl is selected from one or more of halogen, nitro and hydroxyl.

[0053] In the present invention, the R 1 ~R 5 and R 8 All are the same as above, and will not be repeated here.

[0054] The substituted benzaldehyde shown in the formula (1) and the substituted acetone shown in the formula (2) are preferably carried ou...

Embodiment 1

[0084] Embodiment 1: Preparation of Target Compounds I-1~I-24

[0085] Dissolve morpholine (1mmol) in ether (10mL), cool to 0°C in an ice bath, absorb trifluoroacetic acid (1mmol) and dissolve in 5mL ether solution, then slowly add the ether solution of trifluoroacetic acid to morpholine ether In the solution, after incubation for 1 h, return to room temperature, quickly filter off the solvent with a Buchner funnel under reduced pressure, and wash the white solid with diethyl ether (20 mL), repeat 3 times, and use it as a catalyst for the next reaction after drying. Take the prepared catalyst (1mmol), dissolve 3,4-dimethoxybenzaldehyde (5mmol) in 10mL acetone solution, and after reflux reaction for 48h, cool to room temperature, dilute with 20mL ethyl acetate, and wash with saturated NaHCO 3 solution and brine washing (20mL×3), liquid separation, after the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporator under reduced press...

Embodiment 2

[0112] Embodiment 2: the preparation of target compound II-25, II-26

[0113] At 0°C, trimethyl phosphonoacetate (2 mmol) and 2,4-dichlorobenzaldehyde (2.1 mmol) were dissolved in 10 mL of DMF (N,N-dimethylformamide), followed by the slow addition of 28% sodium methoxide dropwise Methanol solution (2mmol), after incubation for 2h, diluted with 20mL distilled water, extracted with ethyl acetate (20mL×3), the organic phase was washed with anhydrous Na 2 SO 4 After drying, the solvent was removed under reduced pressure to obtain a crude product, which was separated by column chromatography (petroleum ether: ethyl acetate = 20:1) to obtain a total of 0.45 g (1.93 mmol) of the target compound II-25 as a white solid. The yield was 92%, m.p. 113-115°C. 1 H NMR (500MHz, Chloroform-d) δ8.01 (d, J = 16.0Hz, 1H), 7.55 (d, J = 8.5Hz, 1H), 7.44 (d, J = 2.1Hz, 1H), 7.28–7.25 (m,1H),6.41(d,J=16.0Hz,1H),3.82(s,3H). 13 C NMR (125MHz, Chloroform-d) δ166.7, 139.4, 136.4, 135.5, 131.3, 130.0,...

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Abstract

The invention provides a dehydrozingerone derivative as shown in the description. R<1>-R<5> are each independently selected from hydrogen or halogen or a nitro group or an alkyl group or a substitutedalkoxy group or an alkoxy group or a hydroxyl group; the substituent in the substituted alkoxy group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; R<6> and R<7> areeach independently selected from hydrogen or halogen or nitrogen-containing heterocycle; R<8> is selected from an alkyl group or an alkoxy group or a substituted alkoxy group; the substituent in thesubstituted alkyl group is selected from one or multiple of halogen, a nitro group and a hydroxyl group; X is selected from a hetero atom or a hydroxylamine group. The dehydrozingerone derivative hasbroad-spectrum activity against plant pathogenic fungi and bacteria, and has certain nematicidal activity, and is a lead compound with the broad biological activity.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a dehydrozingerone derivative, its preparation method and application. Background technique [0002] The research and development costs of pesticides have increased significantly over the past few years. Finding active lead compounds from natural products followed by structural modification or derivatization has proven to be a successful approach to discover pesticides with new modes of action, such as pyrethroid insecticides, neonicotinoid insecticides, and methoxyacrylic acid Ester fungicides. The fresh rhizome of ginger (zingiber officinale Rosc) is recognized as a plant resource for medicine and food by the Ministry of Health of the People's Republic of China. Dehydrozingerone (A, figure 1 ) is one of the chemical constituents in ginger, which was first isolated from African soybean in 1976. Subsequently, its pharmacological activities such as antifungal ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/248C07C49/235C07C49/217C07C49/255C07C205/45C07C69/65C07C251/40C07C45/74C07C67/343C07C249/08C07C201/12A01P1/00A01P3/00A01P5/00
CPCC07C49/248C07C49/235C07C49/217C07C49/255C07C205/45C07C69/65C07C251/40
Inventor 孙然锋宋祥民朱新月梁财张萌
Owner HAINAN UNIVERSITY
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