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Osthole ester derivatives, preparation method and application thereof

A technology of osthole and its derivatives, which is applied in the direction of botany equipment and methods, applications, biocides, etc., can solve the problems of general activity and narrow spectrum of insecticidal action, and achieve simple preparation process, high yield, and excellent killing effect. The effect of insect activity

Active Publication Date: 2020-10-02
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the parent body of osthole has certain insecticidal activity, its insecticidal action spectrum is narrow and its activity is average, which is difficult to meet the market demand. Therefore, its structure is optimized in order to develop better osthole derivatives for insecticidal, preparation Natural Product Insecticides with Better Effects

Method used

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  • Osthole ester derivatives, preparation method and application thereof
  • Osthole ester derivatives, preparation method and application thereof
  • Osthole ester derivatives, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The synthesis of embodiment 1 osthole ester derivatives

[0037] (1) Synthesis of Thioosthole (b)

[0038] Dissolve 486mg of osthole and 809mg of Lawson's reagent in anhydrous tetrahydrofuran, heat to reflux at 66°C, and detect by TLC. After 24 hours, the reaction is completed. The reaction solution is concentrated under reduced pressure and separated by column chromatography to obtain 351mg of thiocnidium. prime (b).

[0039] Physicochemical properties of compound (b):

[0040] 1), yellow solid, melting point 118-120°C;

[0041] 2), the infrared spectrogram feature (IR) feature of compound (b):

[0042] Using potassium bromide tablet method: 2964, 2927cm -1 Stretching vibration absorption for saturated hydrocarbons, 1597, 1549, 1504cm -1 For the absorption of aromatic ring stretching vibration, 1130, 1255cm -1 It is C-O-C stretching vibration absorption.

[0043] 3), the nuclear magnetic resonance spectrum characteristic of compound (b): 1 H NMR (400MHz, CDCl ...

Embodiment 2

[0059] The synthesis (compound 2) of embodiment 2 osthole ester derivatives

[0060] Using the method described in Example 1, compound (c) reacts with 3-bromobenzoic acid to synthesize compound 2. The structure and physicochemical properties of compound 2 are as follows:

[0061]

[0062] 1), pale yellow solid, melting point 140-142°C;

[0063] 2), the infrared spectrogram feature (IR) feature of this compound:

[0064] Using potassium bromide tablet method: 3069cm -1 It is unsaturated hydrocarbon stretching vibration absorption, 2924cm -1 Stretching vibration absorption for saturated hydrocarbons, 1747cm -1 Absorbing stretching vibration for ester carbonyl group, 1583cm -1 It is the vibration absorption of aromatic ring C-C skeleton, 1240, 1090cm -1 It is C-O-C stretching vibration absorption.

[0065] 3), the nuclear magnetic resonance spectrum characteristic of this compound: 1 H NMR (400MHz, CDCl 3 )δ:8.33(s,1H,-Ar),8.11(d,J=8.0Hz,1H,-Ar),7.70-7.73(m,1H,-Ar),7.3...

Embodiment 3

[0066]Synthesis of embodiment 3 osthole ester derivatives (compound 3)

[0067] Using the method described in Example 1, compound (c) reacts with 2-methoxybenzoic acid to synthesize compound 3. The structure and physicochemical properties of compound 3 are as follows:

[0068]

[0069] 1), white solid, melting point 150-152°C;

[0070] 2), the infrared spectrogram feature (IR) feature of this compound:

[0071] Using potassium bromide tablet method: 3075, 3004cm -1 Stretching vibration absorption for unsaturated hydrocarbons, 2928, 2838cm -1 Stretching vibration absorption for saturated hydrocarbons, 1735cm -1 Absorbing stretching vibration for ester carbonyl group, 1582cm -1 It is the vibration absorption of aromatic ring C-C skeleton, 1259,1063cm -1 It is C-O-C stretching vibration absorption.

[0072] 3), the nuclear magnetic resonance spectrum characteristic of this compound: 1 H NMR (400MHz, CDCl 3 )δ: 8.14(d,J=8.8Hz,2H,-Ar),7.09-7.14(m,2H,-Ar),6.92(d,J=8.8Hz,2...

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Abstract

The invention discloses osthole ester derivatives, a preparation method of the derivatives and an application of the derivatives as an insecticide. A chemical structural general formula of the derivatives is represented by a general formula (I) shown in the specification, wherein R is selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl or n is 0 to 3; the substituted phenyl is phenyl substituted with C1-C4 alkyl, C1-C4 alkoxy, halogen, nitro, an aldehyde group or cyano; the substituted pyridyl is pyridyl substituted with C1-C4 alkyl, C1-C4 alkoxy, halogen, nitro, an aldehyde group or cyano; and the R1 is one or more selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, halogen, nitro, an aldehyde group and cyano. Compared with the prior art, the novel osthole ester derivatives provided by the invention have excellent insecticidal activity and high efficiency and low toxicity, and especially has strong growth and development inhibition and toxic activityon third-instar early-stage armyworms, and are expected to be used to prepare the novel natural product insecticide; and in addition, the preparation process is simple, the cost is low, and the yieldis high.

Description

technical field [0001] The invention belongs to the technical field of osthole ester derivatives, and in particular relates to an osthole ester derivative, a preparation method and application thereof. Background technique [0002] [0003] Osthole (Osthole, structural formula above), also known as methoxyparsrol or parsrol, is the first natural coumarin compound extracted and isolated from Umbelliferae plants, in Cnidium [Cnidium monnieri (L.) Cuss] is the most abundant in the dry mature fruit, and it exists in Cnidium, Angelica, Lovage, Parsley, etc. of Umbelliferae, as well as Citrus, Citrus and other plants of Rutaceae ( Yin, Q.J., Sun, H.F. Pharmacological effects and research of osthole as a biological pesticide. Information on Traditional Chinese Medicine. 2009, 26(2), 13-15.). [0004] In terms of structure optimization and derivative synthesis of osthole, the C-3 trifluoromethoxy substituted osthole derivatives prepared by You et al. Has a good inhibitory effec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/60C07D401/12A01N43/40A01P7/04
CPCA01N43/40C07D215/60C07D401/12
Inventor 杨瑞阁郭勇刘芝延侯恩华马楠楠
Owner ZHENGZHOU UNIV
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