CN108794471A - The synthetic method and its agricultural biological activity of benzimidazoles compound - Google Patents
The synthetic method and its agricultural biological activity of benzimidazoles compound Download PDFInfo
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- CN108794471A CN108794471A CN201810983322.0A CN201810983322A CN108794471A CN 108794471 A CN108794471 A CN 108794471A CN 201810983322 A CN201810983322 A CN 201810983322A CN 108794471 A CN108794471 A CN 108794471A
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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Abstract
The present invention proposes a kind of synthetic method and its agricultural biological activity of benzimidazoles compound, belong to organic synthesis field, this method is raw materials used at low cost, reaction system without heating, low energy consumption, it is environmental-friendly, products collection efficiency is high, provide a kind of brand-new method for the synthesis of benzimidazoles compound.The technical solution includes that phenylimidazole compounds and phenolic compound are separately added into reaction vessel, under palladium and isopropanol effect, is reacted 4-6 hours under blue LED lamp illumination condition at 20-25 DEG C；After reaction, pillar layer separation is carried out, benzimidazoles compound is obtained.The present invention can be applied in the preparation of benzimidazoles compound and the bacteria-treating of crops.
Description
Technical field
The invention belongs to the synthetic methods of organic synthesis field more particularly to a kind of benzimidazoles compound and its agricultural
Bioactivity.
Background technology
Benzimidazoles compound is widely present in various natural products, has a variety of biologies such as antimicrobial, antibacterial
Activity is the important intermediate of synthetic perfume, medicine, pesticide and dyestuff.
The existing synthetic method about benzimidazoles compound has very much, such as：With halobenzene and phenylimidazole class
Conjunction object is raw material, is acted in palladium diacetate, potassium carbonate, tricyclohexyl phosphine tetrafluoro boric acid and trimethylace tonitric, in N, N- dimethyl
It is reacted 16 hours at 100 DEG C in ether, products collection efficiency is 95% (Marhadour Sophie et al, Tetrahedron
Letters,2012,vol.53,#3,p.297-300)；Using phenyl boric acid and phenylimidazole compounds as raw material, in four (triphens
Base phosphine) palladium, sodium carbonate effect, in 1,2- ethanedioic acids dimethyl ether, water 100 DEG C react 2 hours, products collection efficiency be 88% (Xiao
Xinsheng et al,Organic Letters,2015,vol.17,#16,p.3998-4001)。
But when using above method synthesizing benzimidazole class compound, it is both needed to using difficulties such as phenylhydrazine, phenyl boric acid or halobenzenes
The raw material of synthesis, and reaction system needs to heat, and not only cost is higher, but also environment is unfriendly.
Invention content
The present invention proposes a kind of synthetic method and its agricultural biological activity of benzimidazoles compound, former used in this method
Expect it is at low cost, reaction system without heating, low energy consumption, environmental-friendly, products collection efficiency is high, be the synthesis of benzimidazoles compound
Provide a kind of brand-new method.
In order to achieve the above object, the present invention provides a kind of synthetic method of benzimidazoles compound, including it is as follows
Step：
It is separately added into phenylimidazole compounds and phenolic compound into reaction vessel, is acted in palladium and isopropanol
Under, it is reacted 4-6 hours under blue LED lamp illumination condition at 20-25 DEG C；
After reaction, pillar layer separation is carried out, benzimidazoles compound is obtained.
Preferably, the phenylimidazole compounds have following (A) structural formula：
Wherein, R1Selected from-OCH3Or-H, R2Selected from-CH3Or-H, R3Selected from-CH3,-H or-Cl.
Preferably, the phenolic compound is phenol or p-trifluoromethyl-phenol.
Preferably, the benzimidazoles compound has following (B) structural formula：
Wherein, R1Selected from-Ph or-H, R2Selected from OCH3Or-H, R3Selected from-CF3Or-H, R4Selected from-CH3Or-H, R5Selected from-
CH3,-H or-Cl.
Preferably, mM ratio of the phenylimidazole compounds and phenolic compound is 1:1-1:2.
Preferably, the phenylimidazole compounds are 1 with mM ratio of palladium and isopropanol:0.001:2-1:
0.002:3。
Preferably, the chromatographic column used in the pillar layer separation is silicagel column, the eluant, eluent used is ethyl acetate
With the mixed solvent of petroleum ether, volume ratio 1:5-2:1.
The present invention also provides a kind of chemical combination that the synthetic method according to any of the above-described technical solution synthesizes
Application of the object in preventing crops germ.
Compared with prior art, the advantages and positive effects of the present invention are：
Synthetic method provided by the present invention directly uses phenylimidazole compounds and phenolic compound cheap and easy to get
Facilitate the synthetic reaction of such compound for raw material, it is raw materials used at low cost, reaction system without heating, low energy consumption, environment
Friendly, products collection efficiency height, a kind of brand-new method is provided for the synthesis of benzimidazoles compound.
Specific implementation mode
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
The every other embodiment that technical staff is obtained without making creative work belongs to the model that the present invention protects
It encloses.
An embodiment of the present invention provides a kind of synthetic methods of benzimidazoles compound, include the following steps：
S1：Phenylimidazole compounds and phenolic compound are separately added into reaction vessel, in palladium and isopropanol
Under effect, reacted 4-6 hours under blue LED lamp illumination condition at 20-25 DEG C.
In this step, using phenylimidazole compounds and phenolic compound come synthesizing benzimidazole class compound, tool
Body, under illumination condition, palladium catalyst is reacted with phenolic compound generates aryl palladium intermediate, this intermediate and phenylimidazole
The reaction of class compound generates target product.What needs to be explained here is that the step reaction is without heating, catalyst amount is extremely low,
Energy consumption can be reduced while reducing cost of material, kept environmental-friendly；In addition, this method is selectively good, products collection efficiency can be high
Up to 95% or more.It is understood that being in the illumination condition that LED light is 10W for the reaction time set in the step
Lower setting, those skilled in the art can adjust the reaction time according to LED light illumination condition combination real reaction situation, as long as ensuring
Reaction raw materials reaction is abundant.
S2：After reaction, pillar layer separation is carried out, benzimidazoles compound is obtained.
In a preferred embodiment, the phenylimidazole compounds have following (A) structural formula：
Wherein, R1Selected from-OCH3Or-H, R2Selected from-CH3Or-H, R3Selected from-CH3,-H or-Cl.
In a preferred embodiment, the phenolic compound is phenol or p-trifluoromethyl-phenol.
In a preferred embodiment, the benzimidazoles compound has following (B) structural formula：
Wherein, R1Selected from-Ph or-H, R2Selected from OCH3Or-H, R3Selected from-CF3Or-H, R4Selected from-CH3Or-H, R5Selected from-
CH3,-H or-Cl.
The concrete structure formula of phenylimidazole compounds used in specifically being defined in above-described embodiment, it is possible to understand that
It is that the phenylimidazole compounds defined in the present embodiment are the compound being derived based on phenylimidazole, structure
It is relatively simple, but be not precluded in the present embodiment and finally obtained by the more complicated phenylimidazole derivatives of structure to prepare the present invention
The benzimidazoles compound obtained.
In a preferred embodiment, mM ratio of the phenylimidazole compounds and phenolic compound is 1:1-1:2.
In the present embodiment, the addition for participating in reaction raw materials is shown in particular, wherein the addition of phenolic compound is relative to phenyl miaow
Azole compounds can be equivalent or it is excessive be added, can ensure that the abundant anti-of phenylimidazole compounds and phenolic compound in this way
It answers；In a preferred embodiment, the phenylimidazole compounds and mM ratio of palladium and isopropanol are 1:0.001:
2-1:0.002:3.In the present embodiment, the addition of palladium and isopropanol relative to phenylimidazole compounds can be equivalent or
It is excessive to be added, it can ensure that the reaction was complete for whole system in this way, expected compound be prepared.
In a preferred embodiment, the chromatographic column used in the pillar layer separation is silicagel column, and the eluant, eluent used is
The mixed solvent of ethyl acetate and petroleum ether, volume ratio 1:5-2:1.In the present embodiment, silicon is utilized to reaction products therefrom
Rubber column gel column carries out gradient elution, to isolated expected synthetic product.According to the similar principle and in view of synthetic product of mixing
Polarity size, it is 1 that volume ratio is selected in the present embodiment:5-2:1 ethyl acetate and the mixed solvent of petroleum ether carry out gradient and wash
De-, in the range, those skilled in the art can be adjusted according to actual conditions.
The embodiment of the present invention additionally provides what a kind of synthetic method according to any of the above-described embodiment synthesized
Application of the compound in preventing crops germ.Specifically, the above-mentioned compound being prepared can be efficiently applied to apple corruption
In the prevention of rotten germ and botrytis cinerea, optional medication alone or in combination as needed.
In order to become apparent from introduce in detail the benzimidazoles compound that the embodiment of the present invention is provided synthetic method and
Its agricultural biological activity, is described below in conjunction with specific embodiment.
Embodiment 1
1mmol 2- phenylimidazoles simultaneously [1,2- α] pyridine, 1mmol phenol, 0.001mmol are separately added into reaction vessel
Palladium and 2ml isopropanols react 4 hours at 20-25 DEG C under 10W blue LED lamps illumination condition；After reaction, it carries out
Pillar layer separation obtains following (1) compound：
Magnetic resonance spectroscopy analysis is carried out to above-mentioned white solid powder, data are as follows：
1HNMR(400MHz,CDCl3)：δ 7.96 (d, J=6.9Hz, 1H), 7.77-7.58 (m, 3H), 7.60-7.46 (m,
5H), 7.38-7.19 (m, 4H), 6.79 (ddd, J=6.8,6.8,1.2Hz, 1H)；
13CNMR(100MHz,CDCl3)：δ144.9,142.6,134.0,130.8,129.9,129.6,128.6,128.3,
128.1,128.0,127.3,124.7,123.0,121.2,117.5,112.7；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 2,3- bisbenzimidazoles simultaneously [1,2- α pyrroles
Pyridine], yield 98%.
Embodiment 2
1mmol 3- (2- methoxyphenyls) imidazo [1,2- α] pyridine, 1mmol benzene are separately added into reaction vessel
Phenol, 0.001mmol palladiums and 2ml isopropanols react 4 hours at 20-25 DEG C under 10W blue LED lamps illumination condition；Reaction
After, pillar layer separation is carried out, following (2) compound is obtained：
Magnetic resonance spectroscopy analysis is carried out to above-mentioned brown solid powder, data are as follows：
1HNMR(400MHz,CDCl3)：δ 8.26 (ddd, J=7.0,1.2,1.1Hz, 1H), 7.70 (ddd, J=9.1,
1.2,1.1Hz, 1H), 7.63 (dd, J=7.5,1.8Hz, 1H), 7.46-7.33 (m, 5H), 7.20 (ddd, J=9.1,6.7,
1.3Hz, 1H), 7.02 (ddd, J=7.5,7.4,1.1Hz, 1H), 6.82 (dd, J=8.3,1.0Hz, 1H), 6.78 (ddd, J=
6.9,6.8,1.2Hz,1H),3.36(s,3H)；
13CNMR(100MHz,CDCl3)：δ156.8,144.6,140.8,132.0,130.9,129.4,129.2,128.7,
127.9,124.3,123.8,123.2,122.9,120.7,118.0,112.5,111.0,54.9；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 2- phenyl -3- (2- methoxyphenyls) miaow
Azoles simultaneously [1,2- α] pyridine, yield 97%.
Embodiment 3
Be separately added into reaction vessel 1mmol 3- phenylimidazoles simultaneously [1,2- α] pyridine, 1mmol to trifluoromethylbenzene
Phenol, 0.001mmol palladiums and 2ml isopropanols react 6 hours at 20-25 DEG C under 10W blue LED lamps illumination condition；Reaction
After, pillar layer separation is carried out, following (3) compound is obtained：
Magnetic resonance spectroscopy analysis is carried out to above-mentioned brown solid powder, data are as follows：
1HNMR(400MHz,CDCl3)：δ 8.02 (d, J=6.9Hz, 1H), 7.76 (d, J=8.1Hz, 2H), 7.72 (d, J
=9.1Hz, 1H), 7.66-7.54 (m, 4H), 7.36-7.16 (m, 4H), 6.77 (dd, J=6.7,6.5Hz, 1H)；
13CNMR(100MHz,CDCl3)：δ145.2,143.6,133.8,131.0,130.8,128.6,128.4,127.9,
126.6,126.2,125.2,123.0,121.9,119.7,117.9,117.5,112.9；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 2- (4- trifluoromethyls) -3- benzos
Imidazo [1,2- α] pyridine, yield 96%.
Embodiment 4
Be separately added into reaction vessel 1mmol 7- methyl -3- phenylimidazoles simultaneously [1,2- α] pyridine, 1mmol phenol,
0.001mmol palladiums and 2ml isopropanols react 6 hours at 20-25 DEG C under 10W blue LED lamps illumination condition；Reaction knot
Shu Hou carries out pillar layer separation, obtains following (4) compound：
Magnetic resonance spectroscopy analysis is carried out to above-mentioned brown solid powder, data are as follows：
1HNMR(400MHz,CDCl3)：δ 7.85 (d, J=7.0Hz, 1H), 7.68 (d, J=7.6Hz, 2H), 7.59-7.36
(m, 6H), 7.34-7.24 (m, 3H), 6.59 (d, J=6.8Hz, 1H), 2.43 (s, 3H)；
13CNMR(100MHz,CDCl3)：δ145.5,142.1,135.8,134.4,130.9,130.1,129.6,128.8,
128.4,128.1,127.4,122.8,120.6,115.7,115.0,21.6；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis be 7- methyl -2,3- bisbenzimidazole simultaneously
[1,2- α] pyridine, yield 95%.
Embodiment 5
1mmol 8- trifluoromethyl -3- phenylimidazoles simultaneously [1,2- α] pyridine, 1mmol benzene are separately added into reaction vessel
Phenol, 0.001mmol palladiums and 2ml isopropanols react 5 hours at 20-25 DEG C under 10W blue LED lamps illumination condition；Reaction
After, pillar layer separation is carried out, following (5) compound is obtained：
Magnetic resonance spectroscopy analysis is carried out to above-mentioned yellow solid powder, data are as follows：
1HNMR(400MHz,CDCl3)：δ8.26(s,1H),7.82-7.71(m,1H),7.70-7.65(m,2H),7.58-
7.52(m,3H),7.48-7.43(m,2H),7.39-7.25(m,4H)；
13CNMR(100MHz,CDCl3)：δ144.8,144.4,133.5,130.6,130.0,129.8,128.9,128.6,
128.2,128.2,125.9,122.4,121.8,120.6,118.4,116.8；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis is 8- trifluoromethyl -2,3- bisbenzimidazoles
And [1,2- α] pyridine, yield 98%.
Embodiment 6
Be separately added into reaction vessel the chloro- 3- phenylimidazoles of 1mmol 8- simultaneously [1,2- α] pyridine, 1mmol phenol,
0.001mmol palladiums and 2ml isopropanols react 5 hours at 20-25 DEG C under 10W blue LED lamps illumination condition；Reaction knot
Shu Hou carries out pillar layer separation, obtains following (6) compound：
Magnetic resonance spectroscopy analysis is carried out to above-mentioned yellow solid powder, data are as follows：
1HNMR(400MHz,CDCl3)：δ 7.98 (dd, J=2.0,0.9Hz, 1H), 7.67-7.58 (m, 3H), 7.57-
7.49 (m, 3H), 7.46-7.40 (m, 2H), 7.32-7.21 (m, 3H), 7.15 (dd, J=9.5,2.0Hz, 1H)；
13CNMR(100MHz,CDCl3)：δ143.7,143.2,133.6,130.7,129.8,129.4,129.4,128.4,
128.1,127.9,126.3,121.7,121.1,120.7,118.2；
After identified, spectral data is corresponding with structural formula, it was demonstrated that synthesis be chloro- 2, the 3- bisbenzimidazoles of 8- simultaneously [1,
2- α] pyridine, yield 95%.
Performance test
The untested compound of above-mentioned synthesis is weighed into 30mg respectively, 3mL acetone is then added, dissolving respectively is configured to
The liquid mother liquor of 10000mg/L concentration；The above-mentioned mother liquors of 0.5mL are taken, are separately added into 2mL acetone, molten even to be configured to 2000mg/L dense
The liquid of degree.Two kinds of liquids respectively take 1mL to be added separately in the PDA culture medium of 100mL meltings, mix well, and band poison training is made
Base is supported, which is distributed equally and is poured in 6 6cm culture dishes, tablet is cooled into.1mL acetone is taken to be added to 100mL meltings
Blank control (CK) is done in PDA culture medium.Bacteria cake is coupled in the above-mentioned PDA culture medium containing liquid and is cultivated, it is each to locate
Reason is in triplicate.Plate seal after inoculation is put into culture in incubator (28 DEG C), when blank control strain bacterium colony grows to training
When foster ware about 3/4, colony diameter is measured, calculates bacterium colony growth inhibition ratio, measurement result is shown in Table 1.
Bacterium colony growth inhibition ratio：Inhibiting rate/%=[control colony diameter-processing colony diameter]/control colony diameter ×
100
1 each compound of table is in 20mg/L to the inhibition percentage of growth of pathogenic bacteria
| Compound | Valsa mali | Botrytis cinerea |
| Embodiment 1 | 93 | 86 |
| Embodiment 2 | 99.6 | 98 |
| Embodiment 3 | 96 | 88.2 |
| Embodiment 4 | 76 | 81 |
| Embodiment 5 | 85.8 | 98.3 |
| Embodiment 6 | 99 | 97 |
From the data in table 1, it can be seen that by the compound prepared by the above embodiment of the present invention 1-6 for Valsa mali and kind
Solanum cinerea bacterium has preferable bacteriostasis, wherein embodiment 2,6 can reach the bacteriostasis of Valsa mali
99% or more, embodiment 2,5 can reach 98% or more for the bacteriostasis of botrytis cinerea.Therefore, in order to effectively inhibit
The compound that above-described embodiment preparation is used alone or in combination may be selected, to obtain better fungistatic effect in above-mentioned germ.
Claims (8)
1. a kind of synthetic method of benzimidazoles compound, which is characterized in that include the following steps：
Phenylimidazole compounds and phenolic compound are separately added into reaction vessel, under palladium and isopropanol effect,
It is reacted 4-6 hours under blue LED lamp illumination condition at 20-25 DEG C；
After reaction, pillar layer separation is carried out, benzimidazoles compound is obtained.
2. synthetic method according to claim 1, which is characterized in that the phenylimidazole compounds have following (A)
Structural formula：
Wherein, R1Selected from-OCH3Or-H, R2Selected from-CH3Or-H, R3Selected from-CH3,-H or-C l.
3. synthetic method according to claim 1, which is characterized in that the phenolic compound is for phenol or to trifluoromethyl
Phenol.
4. synthetic method according to claim 1, which is characterized in that the benzimidazoles compound has following (B)
Structural formula：
Wherein, R1Selected from-Ph or-H, R2Selected from OCH3Or-H, R3Selected from-CF3Or-H, R4Selected from-CH3Or-H, R5Selected from-CH3、-
H or-C l.
5. synthetic method according to claim 1, which is characterized in that the phenylimidazole compounds and phenolic compound
MM ratio be 1:1-1:2.
6. synthetic method according to claim 1, which is characterized in that the phenylimidazole compounds and palladium and different
MM ratio of propyl alcohol is 1:0.001:2-1:0.002:3.
7. synthetic method according to claim 1, which is characterized in that the chromatographic column used in the pillar layer separation is silicon
Rubber column gel column, the eluant, eluent used are the mixed solvent of ethyl acetate and petroleum ether, volume ratio 1:5-2:1.
8. the compound synthesized according to claim 1-7 any one of them synthetic methods is in preventing crops germ
Using.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002048146A2 (en) * | 2000-12-13 | 2002-06-20 | Basf Aktiengesellschaft | Use of substituted imidazoazines, novel imidazoazines, methods for the production thereof, and agents containing these compounds |
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2018
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002048146A2 (en) * | 2000-12-13 | 2002-06-20 | Basf Aktiengesellschaft | Use of substituted imidazoazines, novel imidazoazines, methods for the production thereof, and agents containing these compounds |
Non-Patent Citations (2)
| Title |
|---|
| JOANA F. CAMPOS ET AL.: "Direct Arylation of Imidazo[1,2-a]pyridine at C-3 with Aryl Iodides, Bromides, and Triflates via Copper(I)-Catalyzed C-H Bond Functionalization", 《ORGANIC LETTERS》 * |
| SARADHI KALARI ET AL.: "On water direct arylation of imidazo[1,2-a]pyridines with aryl halides", 《TETRAHEDRON LETTERS》 * |
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