CN103918669A - Application of benzofuroxan derivatives to medicines resisting plant pathogenic fungi - Google Patents
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Abstract
The invention provides an application of benzofuroxan derivatives to medicines resisting plant pathogenic fungi. According to the invention, the benzofuroxan derivatives are used for resisting plant pathogenic fungi, and compounds with good activities are provided, thus providing new selection for plant fungicidal agents, and being beneficial to solution of the problem that the control effect of the fungicidal agent is reduced or lost due to the factor that the pathogenic bacteria are resistant to the fungicidal agent singly used for a long time.
Description
Technical field
The present invention relates to the application of a kind of benzofuraxan derivative in the medicine as anti-plant pathogenic fungi, belong to plant antifungal drug technical field.
Background technology
China is a populous large agricultural country, and grain security is produced concerning national economy and social stability.Plant disease is one of important restriction factor of crops good quality and high output always.In plant disease, it is caused that 70%～80% disease is that disease fungus infects.Fungal diseases of plants not only directly causes crop yield to decline to reduce with quality, and part disease fungus is in infection crops process, can secrete to produce multiplely to the harmful toxin of people and animals and metabolite, and the safety of agricultural product is formed to great threat.
Chemical method is the major measure of control plant epiphyte always, but the preparation of application much has certain limitation or caused germ to develop immunity to drugs to it at present.As: China mainly adopts antibiotic jinggangmeisu to prevent and treat rice sheath blight disease at present, and basic controlling the serious harm of banded sclerotial blight, still, jinggangmeisu is not because have an interior suction therapeutic action, and in the natural world inefficacy of easily degrading, so it is unstable usually to show as control efficiency; Along with the medicaments such as phenylamide, methoxy acrylic, carboxylic acyloxy amine are in succession for the improvement of Phytophthora capsici disease, As time goes on, pathogen produces gradually to the resistance of various medicaments; Equally, for fusarium graminearum, mainly utilize at present the benzimidazole germicides such as carbendazim to spray to prevent and treat at jan flowering wheat, but such pharmacy effect target is single, long-term single use is easy to make pathogen to develop immunity to drugs, and then causes effect of chemical control to reduce or lose.So need to seek the compound of other plant epiphyte resisting.
Benzofuraxan had just been synthesized application very early.In recent years, to the Study on Physiological Activity of its derivative find they to cancer cell, bacterium, parasite, leukemia, make chemotherapy medicament sensitive aspect have good activity.
Although have document and patent report to cross the anti-bacterial effect of this compounds, in bacterium and fungi structure, difference is very large, to the activated compound of bacterium tool, not necessarily has antimycotic activity; And different benzofuraxan derivatives, the activity in antimycotic application is not identical yet.
Summary of the invention
In view of the defect of above-mentioned prior art existence, the object of the invention is to propose the application of a kind of benzofuraxan derivative in the medicine as anti-plant pathogenic fungi, can there is good bacteriostatic activity, can solve the problem of plant epiphyte to existing antibacterial agent generation resistance.
Object of the present invention is achieved by the following technical programs:
The application of a kind of benzofuraxan derivative in the medicine as anti-plant pathogenic fungi.
In above-mentioned application, preferably, described plant pathogenic fungi comprises fusarium graminearum (Fusariumgraminearum), Sclerotinia sclerotiorum (Sclerotiniasclerotiorum), Phytophthora capsici germ (Phytophthoracapsici) and Rhizoctonia solani Kuhn (Rhizoctoniasolani).
In above-mentioned application, preferred, described benzofuraxan derivative has formula I structure:
Wherein R
1comprise H ,-Cl, C
2h
5o-, CH
3s-,
R
2comprise-H ,-F ,-Cl or-Br;
R
3comprise-F ,-Cl ,-Br ,-CH
3, C
2h
5-,-CH
3o ,-C
2h
5o,
R
4comprise-H or-NO
2.
Above-mentioned application, preferred, described benzofuraxan derivative is:
wherein R
1for-Cl,
-H, C
2h
5o-, CH
3s-,
or
or described benzofuraxan derivative is:
wherein R
2for-Cl, R
3for
or R
2for-Cl, R
3for
or R
2for-F, R
3for
or R
2for-Cl, R
3for-Cl, or R
2for-Cl, R
3for-CH
3, R
2for-Cl, R
3for-CH
3o, or R
2for-F, R
3for-CH
3o.
Above-mentioned benzofuraxan derivative is to prepare by paranitrochlorobenzene furazan monomeric compound back flow reaction in organic solvent corresponding with substituting group.Embodiment will provide the synthetic method of the benzofuraxan noval chemical compound that has no report in detail.The benzofuraxan compound of having reported, adopts the method for bibliographical information synthetic.
Outstanding effect of the present invention is:
Benzofuraxan derivative is used for anti-plant pathogenic fungi by the present invention, and provide the compound with better activity, thereby for plant antimicrobial provides new selection, be conducive to solve a kind of antibacterial agent of long-term single use and pathogen developed immunity to drugs and the problem that causes pharmacy control efficacy to reduce or lose.
Embodiment
Below just by specific embodiment, method of the present invention is described, but the present invention is not limited thereto.Experimental technique described in following embodiment, if no special instructions, is conventional method; Described reagent and material, if no special instructions, all can be from commercial channels or conventional method prepare.
Embodiment
The present embodiment provides the application of a kind of benzofuraxan derivative in the medicine as anti-plant pathogenic fungi, comprise synthetic benzofuraxan derivative A1-A9, the B1-B3 that has no report, with existing benzofuraxan derivative A10-A18, B4-B7, and benzofuraxan derivative A1-A18, the effect of B1-B7 in anti-plant pathogenic fungi are carried out to test evaluation.
Benzofuraxan derivative A1:
The preparation of benzofuraxan derivative A2:
By compd A 1(50mg, 0.25mmol) be dissolved in (5mL) in acetonitrile, add the chloro-4-fluoroaniline of 3-2.5mmol, reactant liquor refluxes until reacted in acetonitrile.After acetonitrile is removed in decompression, crude product is carried out to column chromatography purification (eluent is carrene/benzinum=1/1), obtain red solid product (70mg, productive rate 91%).The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative A2.Its data are as follows:
HRMS（CI-）m/z?calcd?for?C
12H
6N
4O
3ClF308.0112，found308.0114；
R
f0.3（PE/EA：5/1）；mp：213℃-214℃；
1H?NMR（400MHz，Acetone-d
6）δ9.83（brs，1H），8.55（d，J=8.8Hz，1H），7.76（dd，J=6.4，2.4Hz，1H），7.68–7.56（m，1H），7.49（dd，J=8.8Hz，1H），6.89（d，J=8.8Hz，1H）；
13C?NMR（101MHz，DMSO-d
6）δ155.2（d，J=247.5Hz），144.9，144.0，141.9，137.4，135.1（d，J=3.0Hz），125.9，124.7（d，J=7.1Hz），123.8，120.3（d，J=18.2Hz），117.8（d，J=22.2Hz），102.3。
The preparation of benzofuraxan derivative A3:
By compd A 1(50mg, 0.25mmol) be dissolved in (5mL) in acetonitrile, add 4-bromaniline 2.5mmol, reactant liquor refluxes until reacted in acetonitrile, and decompression is removed and crude product carried out to column chromatography purification (eluent is carrene/benzinum=1/1) after acetonitrile and obtain red solid product (76mg, productive rate 91%).The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative A3.Its data are as follows:
HRMS（CI+）m/z?calcd?for?C
12H
8N
4O
3 79Br334.9780and?C
12H
8N
4O
3 81Br336.9759，found334.9758and336.9756；
R
f0.2（CH
2Cl
2/PE：1/1）；mp：213℃-214℃；
1H?NMR（400MHz，Acetone-d
6）δ9.85（brs，1H），8.52（d，J=8.8Hz，1H），7.69（d，J=8.0Hz，2H），7.56（d，J=8.0Hz，2H），6.92（d，J=8.8Hz，1H）；
13CNMR（75MHz，DMSO-d
6）δ145.0，144.1，141.7，137.4，137.3，132.5，125.7，123.6，118.4，102.2。
The preparation of benzofuraxan derivative A4:
By compd A 1(50mg, 0.25mmol) be dissolved in (5mL) in acetonitrile, add 2-chloroaniline 2.5mmol, reactant liquor refluxes until reacted in acetonitrile.Decompression is removed and crude product is carried out to column chromatography purification (eluent is carrene/benzinum=1/1) after acetonitrile and obtain red solid product (70mg, productive rate 96%).The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative A4.Its data are as follows:
HRMS（CI-）m/z?calcd?for?C
12H
7N
4O
3Cl290.0207，found292.0208；
R
f0.3（PE/EA：5/1）；mp：194℃-196℃；
1H?NMR（400MHz，CDCl
3）δ8.46（d，J=8.8Hz，1H），7.76（brs，1H），7.61（dd，J=14.0，8.0Hz，2H），7.44（dd，J=7.6Hz，1H），7.32（dd，J=7.6Hz，1H），6.67（d，J=8.8Hz，1H）；
13C?NMR（101MHz，DMSO-d
6）δ144.3，144.1，143.1，137.3，134.7，130.7，130.6，129.6，129.2，128.7，123.4，102.4。
The preparation of benzofuraxan derivative A5:
Under stirring by compd A 1(100mg, 0.50mmol) be dissolved in the acetone of 5mL, then add pyrazoles (5.00mmol) in system.Under nitrogen protection, being warming up to 60 DEG C of stirring reactions finished after 3 days.Solvent acetone in pressure reducing and steaming system, residue dry method obtains yellow solid (76mg, productive rate 65%) after mixing sample taking carrene as eluant, eluent column chromatography.The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative A5.Its data are as follows:
HRMS（CI-）m/z?calcd?for?C
9H
5N
5O
3231.0392，found231.0392；
R
f0.7（CH
2Cl
2）；mp：187℃-188℃；
1H?NMR（400MHz，CDCl
3）δ9.02（s，1H），8.64（d，J=8.4Hz，1H），8.22（d，J=8.4Hz，1H），7.92（s，1H），6.68（s，1H）；
13C?NMR（101MHz，DMSO-d
6）δ144.8，144.3，144.0，134.0，133.2，132.5，132.3，116.1，110.9。
The preparation of benzofuraxan derivative A6:
Under stirring by compd A 1(100mg, 0.50mmol) be dissolved in the acetone of 5mL, then add 1,2,4-triazole (5.00mmol) in system.Under nitrogen protection, being warming up to 60 DEG C of stirring reactions finished after 3 days.Solvent acetone in pressure reducing and steaming system, residue dry method obtains yellow solid (80mg, productive rate 69%) after mixing sample taking carrene as eluant, eluent column chromatography.The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative A6.Its data are as follows:
HRMS（CI-）m/z?calcd?for?C
8H
4N
6O
3232.0345，found232.0341；
R
f0.5（CH
2Cl
2）；mp：156℃-158℃；
1H?NMR（400MHz，CDCl
3）δ9.63（s，1H），8.68（d，J=8.4Hz，1H），8.29（d，J=8.0Hz，1H），8.27（s，1H）；
13C?NMR（101MHz，DMSO-d
6）δ153.9，145.9，144.3，143.8，134.1，133.6，130.1，118.5。
The preparation of benzofuraxan derivative A7:
Under stirring, compound (A1) (50mg, 0.25mmol) is dissolved in the ethanol of 5mL, then adds (4-chlorphenyl) methyl mercaptan 0.38mmol, dissolve sodium methoxide (20.3mg, 0.38mmol) with the ethanol of 0.5mL and also dropwise add in reaction system.Under room temperature, stirring reaction after 1 hour finishes.By ethyl acetate (2 times × 50mL) extractive reaction system, after saturated common salt washing organic facies, anhydrous sodium sulfate drying organic facies.After being spin-dried for organic facies, dry method is mixed sample, with PE/EA=5/1 and CH
2cl
2for eluant, eluent column chromatography obtains yellow solid (78mg, productive rate 97%).The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative A7.Its data are as follows:
MS（+ESI）m/z322.2[M+H]
+；
R
f0.3（PE/EA：5/1）；mp：157℃-159℃；
1H?NMR（400MHz，CDCl
3）δ8.35（d，J=7.6Hz，1H），7.35（dd，J=21.6，8.0Hz，4H），7.18（d，J=7.6Hz，1H），4.50（s，3H）；
13C?NMR（101MHz，DMSO-d
6）δ148.9，142.6，138.8，134.1，132.5，132.1，130.9，128.7，122.8，34.0。
The preparation of benzofuraxan derivative A8:
Under stirring, compound (A1) (50mg, 0.25mmol) is dissolved in the ethanol of 5mL, then adds (4-bromophenyl) methyl mercaptan 0.38mmol, dissolve sodium methoxide (20.3mg, 0.38mmol) with the ethanol of 0.5mL and also dropwise add in reaction system.Under room temperature, stirring reaction after 1 hour finishes.By ethyl acetate (2 times × 50mL) extractive reaction system, after saturated common salt washing organic facies, anhydrous sodium sulfate drying organic facies.After being spin-dried for organic facies, dry method is mixed sample, with PE/EA=5/1 and CH
2cl
2for eluant, eluent column chromatography obtains yellow solid (85mg, productive rate 93%).The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative A8.Its data are as follows:
MS（+ESI）m/z366.0[M+H]
+；
R
f0.4（PE/EA：5/1）；mp158℃-160℃；
1H?NMR（400MHz，CDCl
3）δ8.35（d，J=8.0Hz，1H），7.49（d，J=8.0Hz，2H），7.32（d，J=7.6Hz，2H），7.18（d，J=7.6Hz，1H），4.49（s，2H）；
13C?NMR（101MHz，DMSO-d
6）δ148.9，142.5，138.8，134.5，132.5，132.1，131.6，131.2，122.8，121.0，34.1。
The preparation of benzofuraxan derivative A9:
Under stirring, compound (A1) (50mg, 0.25mmol) is dissolved in the ethanol of 5mL, then adds thiophene-2-mercaptan 0.38mmol, dissolve sodium methoxide (20.3mg, 0.38mmol) with the ethanol of 0.5mL and also dropwise add in reaction system.Under room temperature, stirring reaction after 1 hour finishes.By ethyl acetate (2 times × 50mL) extractive reaction system, after saturated common salt washing organic facies, anhydrous sodium sulfate drying organic facies.After being spin-dried for organic facies, dry method is mixed sample, with PE/EA=5/1 and CH
2cl
2for eluant, eluent column chromatography obtains yellow solid (63mg, productive rate 90%).The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative A9.Its data are as follows:
HRMS（CI-）m/z?calcdfor?C
10H
5N
3O
3S
2278.9772，found278.9774；
R
f0.5（PE/EA：5/1）；mp：174℃-176℃；
1H?NMR（400MHz，CDCl
3）δ8.29（d，J=7.6Hz，1H），7.77（d，J=5.2Hz，1H），7.51（d，J=2.8Hz，1H），7.31–7.27（m，1H），6.78（d，J=7.6Hz，1H）；
13C?NMR（101MHz，DMSO-d
6）δ148.0，142.7，140.0，139.5，135.8，133.2，132.4，129.5，123.4，121.4。
The preparation of benzofuraxan derivative B1, B2, B3:
Benzo furoxan b1 50mg is dissolved in the carrene of 2mL, then to the triphenylphosphine that adds 1.5 times of equivalents in system.System heat up and in carrene back flow reaction after 1 hour, finish.Solvent in pressure reducing and steaming system, residue dry method obtains yellow solid (39mg, productive rate 83%) after mixing sample taking PE/EA=5/1 as eluant, eluent column chromatography.The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative B1.Its data are as follows:
HRMS（CI-）calcd?for?C
11H
12ClN
3O?237.0669，found?237.0662；
R
f?0.8（PE/EA：5/1）；mp：77℃-79℃；
1H?NMR（400MHz，CDCl
3）δ7.85（s，1H），7.07（s，1H），3.05（s，4H），1.92–1.69（m，4H），1.69–1.45（m，2H）；
13C?NMR（75?MHz，CDCl
3）δ153.5，149.1，146.9，138.5，116.8，101.2，53.4，25.9，24.0。
Benzo furoxan b2 50mg is dissolved in the carrene of 2mL, then to the triphenylphosphine that adds 1.5 times of equivalents in system.System heat up and in carrene back flow reaction after 1 hour, finish.Solvent in pressure reducing and steaming system, residue dry method obtains yellow solid (40mg, productive rate 85%) after mixing sample taking PE/EA=5/1 as eluant, eluent column chromatography.The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative B2.Its data are as follows:
HRMS（CI-）m/z?calcd?for?C
10H
10N
3O
2Cl?239.0462，found232.0464；
R
f0.3（PE/EA：5/1）；mp：118℃-120℃；
1HNMR（400MHz，CDCl
3）δ7.89（s，1H），7.14（s，1H），4.14–3.69（m，4H），3.34–2.95（m，4H）；
13C?NMR（101MHz，CDCl
3）δ152.1，148.7，146.8，137.5，117.1，101.9，66.6，52.2。
Benzo furoxan b350mg is dissolved in the carrene of 2mL, then to the triphenylphosphine that adds 1.5 times of equivalents in system.System heat up and in carrene back flow reaction after 1 hour, finish.Solvent in pressure reducing and steaming system, residue dry method obtains yellow solid (40mg, productive rate 86%) after mixing sample taking PE/EA=5/1 as eluant, eluent column chromatography.The solid product of gained is carried out to Structural Identification, be defined as benzofuraxan derivative B3.Its data are as follows:
HRMS（CI-）m/z?calcd?for?C
11H
12N
3OF221.0964，found221.0963；
R
f0.5（PE/EA：5/1）；mp：66℃-68℃；
1H?NMR（400MHz，CDCl
3）δ7.32（d，J=11.6Hz，1H），6.92（d，J=7.6Hz，1H），3.22–3.05（m，4H），1.84–1.70（m，4H），1.70–1.58（m，2H）；
13C?NMR（101MHz，CDCl
3）δ160.5（d，J=265.6Hz），148.0，147.8（d，J=16.2Hz），146.4（d，J=15.2Hz），99.3（d，J=27.3Hz），98.5（d，J=3.0Hz），52.1，52.0，25.9，24.1。
The compound that does not provide synthetic route in the present embodiment foregoing is all the known compounds that have report in synthetic method.These compounds adopt the synthetic method of bibliographical information to synthesize, in the hydrogen spectrum with nuclear-magnetism, carbon stave is levied structure and is carried out bacteriostatic activity test below after correct, benzofuraxan derivative A1-A18, B1-B7 is carried out to test evaluation (being bacteriostatic activity test) at the effect of anti-plant pathogenic fungi below.
Bacteriostatic activity test method: adopt respectively paper dish method and mycelial growth inhibition method to carry out primary dcreening operation and the multiple sieve of compound antibacterial activity.
Paper dish method: test strain is made to the bacterium cake that diameter is 0.5cm, be placed in the culture dish central authorities containing PDA medium, 25 DEG C of constant temperature culture to bacterial strain diameters are about 3cm.On the filter paper that the acetone soln of getting 2 μ L concentration and be 10 μ g/ μ L compounds is 0.5cm in diameter, after volatilizing, right-angled intersection is placed in culture dish apart from 1cm place, test strain edge, 4, every ware.Get 10 μ L distilled water on paper dish, constant temperature culture at 25 DEG C, observes strains tested growing state, measures inhibition zone size, gets its mean value as bacteriostatic activity relative strength index: inhibition zone is larger, and bacteriostatic activity is stronger.Repeat 3 times, using acetone as negative control, the positive contrast of cycloheximide.Test strain comprises fusarium graminearum (Fusariumgraminearum), Sclerotinia sclerotiorum (Sclerotiniasclerotiorum), Phytophthora capsici germ (Phytophthoracapsici) and Rhizoctonia solani Kuhn (Rhizoctoniasolani).
Mycelial growth suppresses method: the PDA pastille flat board that primary dcreening operation (paper dish method) the activated compound of tool is configured to serial gradient concentration, test strain bacterium cake is placed in to pastille culture dish central authorities, when 25 DEG C of constant temperature culture to test strain of blank ware are grown to culture dish edge, right-angled intersection method is measured the colony diameter of each pastille flat board, calculate the inhibiting rate of compound to mycelial growth, taking compound concentration as abscissa, inhibiting rate is ordinate, make calibration curve, the concentration of compound when calculating inhibiting rate is 50%, i.e. IC50 value.Repeat to average for 3 times.With carbendazim and the positive contrast of tpn.
Benzofuraxan derivative A1-A18 is as shown in table 1 below to the inhibitory action of several plant disease fungus, uses IC
50value (μ g/mL) represents, suppresses the concentration of half disease fungus growth needs.Numerical value is less, shows that compound is better to the inhibition of plant pathogenic fungi.
Table 1
Benzofuraxan derivative B1-B7 is as shown in table 2 below to the inhibitory action of several plant disease fungus, uses IC
50value (μ g/mL) represents, suppresses the concentration of half disease fungus growth needs.Numerical value is less, shows that compound is better to the inhibition of plant pathogenic fungi.
Table 2
As seen from table, benzofuraxan derivative A1-A18, B1-B7 have demonstrated good antibacterial effect in the application of anti-plant pathogenic fungi.Therefore, benzofuraxan derivative is used for anti-plant pathogenic fungi by the present invention, and provide the compound with better activity, thereby for plant antimicrobial provides new selection, be conducive to solve a kind of antibacterial agent of long-term single use and pathogen developed immunity to drugs and the problem that causes pharmacy control efficacy to reduce or lose.
Claims (4)
1. the benzofuraxan derivative application in the medicine as anti-plant pathogenic fungi.
2. application according to claim 1, is characterized in that: described plant pathogenic fungi comprises one or more in fusarium graminearum, Sclerotinia sclerotiorum, Phytophthora capsici germ and Rhizoctonia solani Kuhn.
3. application according to claim 1, is characterized in that: described benzofuraxan derivative has formula I structure:
Wherein R
1comprise H ,-Cl, C
2h
5o-, CH
3s-,
R
2comprise-H ,-F ,-Cl or-Br;
R
3comprise-F ,-Cl ,-Br ,-CH
3, C
2h
5-,-CH
3o ,-C
2h
5o,
R
4comprise-H or-NO
2.
4. application according to claim 3, is characterized in that: described benzofuraxan derivative is:
wherein R
1for-Cl,
-H, C
2h
5o-, CH
3s-,
or
or described benzofuraxan derivative is:
wherein R
2for-Cl, R
3for
or R
2for-Cl, R
3for
or R
2for-F, R
3for
or R
2for-Cl, R
3for-Cl, or R
2for-Cl, R
3for-CH
3, R
2for-Cl, R
3for-CH
3o, or R
2for-F, R
3for-CH
3o.
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| JPS527055B1 (en) * | 1970-11-27 | 1977-02-26 | ||
| CN103004799A (en) * | 2013-01-06 | 2013-04-03 | 苏州大学 | Application of benzofuroxan derivative to resisting plant pathogenic fungi |
-
2014
- 2014-04-11 CN CN201410145219.0A patent/CN103918669B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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