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Phenanthrene-containing heterocyclic compounds, preparation method thereof and anti-plant virus application

An anti-plant virus agent and heterocyclic technology, applied in the field of pesticides, can solve the problems of high price of original drugs, easy resistance of viruses, and limited application range, and achieve significant anti-plant virus activity and excellent anti-plant virus activity , good environmental compatibility

Active Publication Date: 2016-12-28
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because ribavirin interferes with GMP biosynthesis in plants, consumes GTP in plant cells and interferes with hormone balance in plants, it causes certain phytotoxicity to plants.
Moreover, due to the short duration of the drug effect (only when the drug is applied within 48 hours before the virus infection), it is difficult to grasp the best timing of application in production and application. The original drug is expensive and the virus is prone to drug resistance. The scope of practical application in our country is not wide (An Derong, Life Science, 1994, 6(2), 15-18.)

Method used

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  • Phenanthrene-containing heterocyclic compounds, preparation method thereof and anti-plant virus application
  • Phenanthrene-containing heterocyclic compounds, preparation method thereof and anti-plant virus application
  • Phenanthrene-containing heterocyclic compounds, preparation method thereof and anti-plant virus application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: Synthesis of phenanthrene-containing heterocyclic compound 1:

[0026]

[0027] Synthesis of 2,3,6,7-tetramethoxy-9-phenanthroyl chloride (37)

[0028] Add 0.80g (2.34mmol) of 2,3,6,7-tetramethoxy-9-phenanthroic acid (36) and 20mL oxalyl chloride into a 100mL single-necked bottle; add 2 drops of DMF in a water bath; then naturally rise to room temperature, After reacting for another 3 h, oxalyl chloride was evaporated under normal pressure to obtain 0.82 g of yellow solid 37; it was directly used in the next reaction without further treatment.

[0029] Synthesis of 1-(2,3,6,7-tetramethoxy-9-phenanthroyl)-3-methylpyrazole (1)

[0030] Add 0.23g 3-methylpyrazole, 25mL CH 2 Cl 2 , 0.34g Et 3 N, slowly dropwise add 0.82g of 2,3,6,7-tetramethoxy-9-phenanthroyl chloride (37) prepared above to CH 2 Cl 2 The solution was 20 mL, and after the dropwise addition was completed, it was slowly raised to room temperature and reacted for 2 hours, and TLC detected t...

Embodiment 2

[0031] Embodiment 2: Synthesis of phenanthrene-containing heterocyclic compound 19:

[0032]

[0033] Synthesis of 2,3,6,7-tetramethoxy-9-phenanthrenemethanol (38)

[0034] Add 1.03g of 2,3,6,7-tetramethoxy-9-phenanthroic acid (36) and 20mL THF into a 100mL single-necked bottle; add 0.28g of LiAlH in batches under cooling in an ice-water bath 4 , After the addition is complete, heat to reflux for 1.5h, then cool naturally to room temperature. Add 20 mL of CH to the reaction solution 2 Cl 2 , and then slowly add 1mol / L HCl dropwise in an ice-water bath until the white flocculent precipitate disappears; 2 Cl 2 (10mL×3) extraction; combined organic phase, washed once with saturated NaCl solution, anhydrous NaCl 2 SO 4 dry. Filtrate under reduced pressure and then concentrate to obtain a solid, which is then recrystallized with ethyl acetate to obtain a white solid with a yield of 95.0% and a melting point of 183-185°C. 1 H NMR (400MHz, CDCl 3 )δ7.83(s, 1H), 7.78(s, 1H...

Embodiment 3

[0039] Example 3: Synthesis of phenanthrene-containing heterocyclic compounds 2-18 and 20-35: by repeating the methods of Examples 1 and 2.

[0040] Synthesis of 1-(2,3,6,7-tetramethoxy-9-phenanthroyl)pyrazole (2)

[0041] Yellow solid, yield: 66.7%, melting point: 214-215°C. 1 H NMR (400MHz, CDCl 3 )δ8.47(d, J=2.8Hz, 1H), 7.99(s, 1H), 7.83-7.82(m, 2H), 7.80(s, 1H), 7.57(s, 1H), 7.26(s, 1H ), 6.59-6.58(m, 1H), 4.16(s, 3H), 4.14(s, 3H), 4.03(s, 3H), 3.95(s, 3H); 13 C NMR (100MHz, CDCl 3 I (m / z): calcd.for C 22 h 20 N 2 o 5 Na[M+Na] + 415.1264; found 415.1266.

[0042] Synthesis of 1-(2,3,6,7-tetramethoxy-9-phenanthroyl)imidazole (3)

[0043] Light yellow solid, yield: 79.0%, melting point: 209-210°C. 1 H NMR (400MHz, CDCl 3 )δ8.12(s, 1H), 7.84(s, 2H), 7.81(s, 1H), 7.66(s, 1H), 7.61(s, 1H), 7.24(s, 1H), 7.23(s, 1H ), 4.18(s, 3H), 4.16(s, 3H), 4.04(s, 3H), 3.98(s, 3H); 13 C NMR (100MHz, CDCl 3 I (m / z): calcd.for C 22 h 21 N 2 o 5 [M+H] + 393.1445; found 393....

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Abstract

Disclosed are phenanthrene-containing heterocyclic compounds shown as general formula (I) and preparation method therefor and application thereof on pesticides. The synthetic method of the compounds is simple and easy to industrialize. The phenanthrene-containing heterocyclic compounds can be used as plant virucides to inhibit tobacco mosaic virus, pepper virus, rice virus, tomato virus, sweet potato virus, potato virus, melon virus, maize dwarf mosaic virus and the like, particularly to inhibit tobacco mosaic virus. R1, R2, R3, X1-X7, m and n in general formula (I) are as defined in description.

Description

technical field [0001] The invention relates to a novel anti-plant virus agent and its preparation and application, in particular to a phenanthrene-containing heterocyclic compound as an anti-plant virus agent, and belongs to the technical field of pesticides. Background technique [0002] There are many kinds of plant viruses and their distribution is very wide. In agricultural production, virus diseases are the second largest type of plant diseases after fungi. The vast majority of economic crops are affected by plant viruses, resulting in varying degrees of yield reduction or quality degradation, which is extremely difficult to control and is known as "plant cancer". [0003] At present, antiviral agents are mainly used for the prevention and treatment of plant virus diseases. Many virus inhibitors can only reduce the severity of symptoms. At present, there are not many effective and satisfactory plant virus inhibitors in practical use, especially less effective therapeut...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/56A01N43/50A01N43/52A01N43/78A01N43/76A01N43/40A01N43/653A01N43/647A01N33/10A01P1/00C07D231/12C07D233/60C07D235/30C07D277/46C07D277/82C07D277/74C07D235/28C07D263/58C07D213/75C07D249/14C07D249/12C07D249/18C07D295/096
CPCA01N33/10A01N43/40A01N43/50A01N43/52A01N43/56A01N43/647A01N43/653A01N43/76A01N43/78C07D213/75C07D231/12C07D233/56C07D235/28C07D235/30C07D249/12C07D249/14C07D249/18C07D263/58C07D277/46C07D277/74C07D277/82C07D295/096
Inventor 汪清民王兹稳魏朋王蕾刘玉秀郑彦龙马双王力钟
Owner NANKAI UNIV
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