Quinoline derivative, preparation method and application thereof in prevention and treatment of plant viruses and sterilization

A kind of derivative, quinoline technology, applied in the field of pesticides

Active Publication Date: 2021-04-09
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although alkenyl borocoppers are considered as possible reaction intermediates, coupling reactions utilizing this intermediate with azaarenes have not been reported

Method used

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  • Quinoline derivative, preparation method and application thereof in prevention and treatment of plant viruses and sterilization
  • Quinoline derivative, preparation method and application thereof in prevention and treatment of plant viruses and sterilization
  • Quinoline derivative, preparation method and application thereof in prevention and treatment of plant viruses and sterilization

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preparation example Construction

[0040]The present invention provides a method of preparing a 2-position alkenyl substituted quinoline derivative, including: in the presence of a catalyst, boron reagent, ligand, base, in an organic solvent, a quine (II) The arylioxide represented by the nitride formula to the formula (III) to obtain a compound represented by the formula (I) by selective hydrocarbon bonding.

[0041]

[0042]According to the invention, the compound represented by the formula (II) and the formula (III) can be specifically selected according to the desired formula (I), and R1R2R3R4R5R6And R as described above, the present invention will not be described later.

[0043]Among them, the molar ratio of the quinoline nitrogen oxide shown in the formula (II) and the dirylene of formula (III) is from 1 to 3: 1, preferably from 1 to 2: 1;

[0044]Preferably, the catalyst is Cucl, Cubr, Cui, Cu (OAC)2Cu (OTF)2, Cu (Acac)2One or more of IMES-CUCL, IPR-CUCL;

[0045]The amount of the catalyst can fluctuate in a wider range, su...

Embodiment 1

[0079](E) -2- (1,2-dimstyrene) quinoline (IAA) synthesis

[0080]Quinoline nitrogen oxide IIA (1.5 eq), alkyne (10 mol%), Cucl (10 mol%), Cucl (10 mol%), Cucl (10 mol%), Cucl (10 mol%)3(12 mol%), B2Pin2(1.5 eq), Buok (2.0 eq), 2-methf (0.2 M), after the air was replaced with AR 3 times, heated to 80 ° C, and the reaction was 24 h. After the reaction is complete, the solvent is evaporated and chromatography directly. White solid, melting point 114-115 ° C, 126.0 mg of mass, and 82% yield.1H NMR (400MHz, CDCL3Δ8.17 (D, J = 8.4 Hz, 1H), 7.98 (D, J = 8.8 Hz, 1H), 7.96 (S, 1H), 7.75 (D, J = 8.0 Hz, 1H), 7.74-7.69 ( M, 1H), 7.52-7.47 (m, 1H), 7.44-7.37 (m, 3H), 7.34-7.28 (m, 2H), 7.17-7.12 (m, 5H), 7.10 (D, J = 8.8 Hz, 1h);13C NMR (100MHz, CDCL3Δ159.3, 148.1, 141.1, 139.4, 137.0, 136.1, 132.6, 130.8, 130.3, 129.8, 127.8, 127.6, 127.5, 127.4, 126.3, 121.0.HRMS (ESI): Calcdfor C23Hide18N [m + h]+: 308.1434; Found: 308.1439.

[0081](E) -2- (1,2-double (4-fluorophenyl) vinyl) quinoline (IAB)

[0082]...

Embodiment 2

[0126]Example 2: Determination of anti-tobacco leaf virus activity, as follows:

[0127]1. Virus purification and concentration measurement:

[0128]Refer to the Tobacco Flower Leaf Virus SOP Specification Computed by Nankai University Elements. After the virus crude liquid was centrifuged by 2 polyethylene glycol, the concentration was measured, then reflected at 4 ° C.

[0129]2. Compound solution formulated:

[0130]After weighing, the primary drug was dissolved with DMF with 1 × 105 μg / ml of mother liquor, which was then diluted with 1 ‰ Tween 80 aqueous solution to the desired concentration; Ningnamycin formulation Dilution directly against water.

[0131]3. Friction vaccination of Shanxi smoked blade, rinse with water, virus concentration 10 μg / ml. After cutting, cut, along the leaf medal, and the left and solenoids were immersed in 1 ‰ Temperature water and the medicament. After 30 minutes, the moisturizing culture was moisturized at a suitable illumination temperature, each three leave...

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Abstract

The invention relates to a 2-alkenyl substituted quinoline derivative, a preparation method and application thereof in prevention and treatment of plant viruses and sterilization. The significance of each group in the general formula is shown as the specification. The 2-alkenyl substituted quinoline derivative disclosed by the invention has anti-plant virus activity and broad-spectrum bactericidal activity.

Description

Technical field[0001]The present invention relates to 2 alkenyl substituted quinoline derivatives and preparation methods thereof and in the field of prevention and treatment of plant viruses, sterilization, and is a pesticide technology.Background technique[0002]Quinoline derivatives and their associated nitrogen-containing heterocycles are widely present in natural products, pharmaceutical molecules, and functional materials, and their synthesis and derivatization have always been a hot spot for organic synthesis. Alkenylation in quinoline ring nitrogen atoms typically require pre-functional grouping, including introducing a halogen atom or forming a carbon metal bond, which undoubtedly increases the step of reacting, generating unnecessary by-products, atoms do not meet the reaction Economic. Transition metal catalyzed pyridine rings Direct hydrocarbon bonding is also a common method for introducing a substituent in pyridine or quinoline cyclic nucleus atoms, but the method usual...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/12C07D215/14C07D409/14C07D215/18C07D221/10A01N43/42A01P1/00A01P3/00
CPCC07D215/12C07D215/14C07D409/14C07D215/18C07D221/10A01N43/42
Inventor 汪清民黄源琼宋红健张静静刘玉秀李永强
Owner NANKAI UNIV
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