CN106831635B - A kind of benzo oxygen azatropylidene class bacteriostatic agent and its synthetic method - Google Patents
A kind of benzo oxygen azatropylidene class bacteriostatic agent and its synthetic method Download PDFInfo
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- CN106831635B CN106831635B CN201710103539.3A CN201710103539A CN106831635B CN 106831635 B CN106831635 B CN 106831635B CN 201710103539 A CN201710103539 A CN 201710103539A CN 106831635 B CN106831635 B CN 106831635B
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- SIHWGZGMFDDQBL-UHFFFAOYSA-N O=C(C(C(c(cc1)ccc1Cl)=Nc1c2cccc1)OC2=O)NC1CCCCC1 Chemical compound O=C(C(C(c(cc1)ccc1Cl)=Nc1c2cccc1)OC2=O)NC1CCCCC1 SIHWGZGMFDDQBL-UHFFFAOYSA-N 0.000 description 1
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- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
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Abstract
The present invention relates to a kind of benzo oxygen azatropylidene class bacteriostatic agents and preparation method thereof, and chemical structural formula is：Wherein, substituent R1、R2And R3It is not fixed for chloro or bromo or methyl or normal-butyl or rubigan or methyl acetate base or tert-butyl or cyclohexyl, substituting group position, number and conjugate position.Synthetic method is reacts with a kind of adjacent triazobenzene formic acid compound with the Passerini that aryl ketones aldehyde compound and generated in-situ different nitrile compounds occur, and the product continuation of generation is reacted with triphenyl phosphorus generation Staudinger, intramolecular aza-Wittig reaction cyclization generates the important heterocyclic compounds such as polysubstituted benzo oxygen azatropylidene.The invention key point is the provision of the new synthetic method that a kind of step is few, yield is high to synthesize a kind of novel benzo oxygen azatropylidene class compound.Above compound has preferable inhibitory activity to Rhizoctonia solani, penicillium digitatum and penicillium italicum, can be used as fungicide.
Description
Technical field
The present invention relates to a kind of benzo oxygen azatropylidene analog derivative and its applications as the effective component of fungicide.
Background technique
The invention and application of bacteriostatic agent greatly enhance the ability that the mankind resist bacterium infection.Since nineteen twenty-nine section of Britain
Since scholar's Fleming finds penicillin, bacteriostatic agent is constantly in booming.The type of bacteriostatic agent is by initial penicillin
One kind having risen to thousands of kinds, and application range also extends in livestock and agricultural production from the mankind.However, along with bacteriostatic agent
Extensive extensive use, also there is apparent drug resistance in corresponding germ.Therefore, new bacteriostatic agent is constantly researched and developed
Drug improves the ability that the mankind resist disease caused by the microorganisms such as bacterium, virus, it appears be even more important.
Summary of the invention
The main purpose of the present invention is to provide a kind of benzo oxygen azatropylidene class bacteriostatic agent and its synthetic methods.
Technical scheme is as follows：
A kind of benzo oxygen azatropylidene class bacteriostatic agent, the bacteriostatic agent chemical structural formula are：
Wherein, substituent R1、R2And R3For chloro or bromo or methyl or normal-butyl or rubigan or methyl acetate base or
Tert-butyl or cyclohexyl, R1、R2And R3Substituting group position, number and conjugate position are not fixed.
The method of the synthesis benzo oxygen azatropylidene class bacteriostatic agent, the method includes following synthesis paths：
It the described method comprises the following steps：
(1) under room temperature, adjacent triazobenzene formic acid derivates are added into reaction flask, weighs aryl keto-aldehyde and isonitrile adds
Enter into methylene chloride；
(2) reaction system in the step (1) is placed in and is reacted at room temperature, that is, it is derivative to produce triazobenzene formic acid esters
Object；
(3) reaction solution for taking the step (2) without isolation, it is anti-to issue raw intramolecular Wittig in triphenyl phosphine catalyst
It answers；Residue carries out column chromatographic isolation and purification through silicagel column and obtains target compound；
Complete the synthesis of benzo oxygen azatropylidene class bacteriostatic agent.
The molar feed ratio of the step (1) step (1) neighbour's triazobenzene formic acid derivates, aryl keto-aldehyde and isonitrile
It is 1:1:1.Change feed ratio, the yield of triazobenzene carbamate derivatives can improve a lot；The range of feed ratio is larger, has
Conducive to the production of fine chemicals.
Step (2) reaction temperature is room temperature.Be conducive to reacting balance progress under this reaction temperature, reduce by-product
It generates.It will aggravate higher than the reaction of this reaction temperature, product decomposes.
Described step (2) reaction time 24 hours.Reaction time, then reaction was incomplete less than 24 hours.
Described step (3) reaction time 4~12 hours.Reaction time, then reaction not exclusively, was more than 12 hours less than 4 hours
Then by-product increases.
The present invention has the beneficial effect that：
1. the present invention is with adjacent triazobenzene formic acid derivates and the generation of aryl keto-aldehyde and generated in-situ isonitrile
Passerini reaction, the product of generation without isolation directly with triphenyl phosphorus occur Staudinger react, intramolecular azepine
Wittig reaction cyclization generates the new method of polysubstituted benzo oxygen azatropylidene class bacteriostatic agent；
2. a kind of bacteriostatic agent that the present invention synthesizes is to a variety of gibberella saubinetiis (Gibberella saubinetii), rice blast
Bacterium (Magnaporthegrisea), penicillium italicum (Penicillium italicum) etc. have obvious inhibiting effect；
3. a kind of novel polysubstituted benzo oxygen azatropylidene class different from traditional commerce bacteriostatic agent of present invention synthesis is antibacterial
Agent provides the new synthetic method that a kind of preparation cost is low, easy to operate and high reaction efficiency.
Specific embodiment
The present invention is further illustrated below with reference to embodiment, but the scope of protection of present invention is not limited to implement
The range of example statement.
Instrument and reagent：
Fusing point is measured with X4 type melting point apparatus (production of Beijing third optical instrument factory), and thermometer is not calibrated；1H NMR and13600 type 600MHz core of C NMR 400 type 400MHz Nuclear Magnetic Resonance of Varian Mercury or Varian Mercury
Magnetic resonance device measurement, deuterated chloroform (CDCl3) or deuterated dimethyl sulfoxide (DMSO-d6) it is solvent, TMS is internal standard；MS is used
The measurement of FinniganTrace mass spectrograph；Elemental analysis is measured using Vario ELIII elemental analyser；Agents useful for same is domestic
(or import) chemistry is pure or analysis is pure.Methylene chloride is dried.
Embodiment 1
A kind of synthesis N- (tert-butyl) -2- (4- chlorphenyl) -5- oxo -3,5- dihydrobenzo [e] [1,4] oxygen azepine -3-
The method of formamide, including following experimental procedure：
Adjacent triazobenzene formic acid 1 (0.16g, 1mmol) is weighed, parachloroacetophenone aldehyde 2 (0.17g, 1mmol) and tertiary fourth are weighed
Base isonitrile 3 (0.08g, 1mmol) is added in 5ml methylene chloride, is placed in and is reacted at room temperature 24 hours, that is, produces triazobenzene
Carbamate derivatives；Reaction solution without isolation, is added triphenylphosphine (3.15g, 1.2mmol), occurs under triphenyl phosphine catalyst
Intramolecular wittig reaction；Column chromatographic isolation and purification, which is carried out, through silicagel column after the reaction was completed obtains target compound 4a：
Elemental analysis：64.97 H% of measured value C%, 5.02 N% 7.76
64.78 H% of calculated value C%, 5.16 N% 7.55
1H NMR(CDCl3, 600MHz) and δ (ppm) 7.98 (d, J=6.6Hz, 1H, Ar-H), 7.76-7.69 (m, 3H, Ar-
H),7.46-7.39(m,4H,Ar-H),6.79(s,1H,NH),5.16(s,1H,CH),1.38(s,9H,CH3).
HRMS Calculatedfor[C20H19ClN2O3+H]+:371.1162,Found:371.1157.
Embodiment 2
A kind of synthesis (4- bromophenyl)-N- (tert-butyl) -5- oxo -3,5- dihydrobenzo [e] [1,4] oxygen azepine -3- first
The method of amide, including following experimental procedure：
Adjacent triazobenzene formic acid 1 (0.16g, 1mmol) is weighed, parabromoacetophenone aldehyde 2 (0.21g, 1mmol) and tertiary fourth are weighed
Base isonitrile 3 (0.08g, 1mmol) is added in 5ml methylene chloride, is placed in and is reacted at room temperature 24 hours, that is, produces triazobenzene
Carbamate derivatives；Reaction solution without isolation, is added triphenylphosphine (3.15g, 1.2mmol), occurs under triphenyl phosphine catalyst
Intramolecular wittig reaction；Column chromatographic isolation and purification, which is carried out, through silicagel column after the reaction was completed obtains target compound 4b：
Elemental analysis：57.88 H% of measured value C%, 4.37 N% 6.79
57.84 H% of calculated value C%, 4.61 N% 6.75
1H NMR(CDCl3, 600MHz) and δ (ppm) 7.97 (d, J=7.8Hz, 1H, Ar-H), 7.70-7.56 (m, 5H, Ar-
H),7.45-7.38(m,2H,Ar-H),6.77(s,1H,NH),5.16(s,1H,CH),1.37(s,9H,CH3).
HRMS Calculatedfor[C20H19BrN2O3+H]+:415.0657,Found:415.0670.
Embodiment 3
A kind of synthesis (4- chlorphenyl)-N- cyclohexyl -5- oxo -3,5- dihydrobenzo [e] [1,4] oxygen azepine -3- formyl
The method of amine, including following experimental procedure：
Adjacent triazobenzene formic acid 1 (0.16g, 1mmol) is weighed, parachloroacetophenone aldehyde 2 (0.17g, 1mmol) and hexamethylene are weighed
Base isonitrile 3 (0.11g, 1mmol) is added in 5ml methylene chloride, is placed in and is reacted at room temperature 24 hours, that is, produces triazobenzene
Carbamate derivatives；Reaction solution without isolation, is added triphenylphosphine (3.15g, 1.2mmol), occurs under triphenyl phosphine catalyst
Intramolecular wittig reaction；Residue carries out column chromatographic isolation and purification through silicagel column and obtains target compound 4c：
Elemental analysis：66.82 H% of measured value C%, 5.24 N% 7.33
66.58 H% of calculated value C%, 5.33 N% 7.06
1H NMR(CDCl3, 600MHz) and δ (ppm) 7.98 (d, J=7.8Hz, 1H, Ar-H), 7.74-7.69 (m, 3H, Ar-
H),7.46-7.40(m,4H,Ar-H),6.91(s,1H,NH),5.24(s,1H,CH),3.79(s,1H,CH),1.97-1.74
(m,4H,CH2),1.34-1.17(m,6H,CH2).
HRMS Calculatedfor[C22H21ClN2O3+H]+:397.1319,Found:397.1341.
Embodiment 4
A kind of synthesis (4- bromophenyl)-N- cyclohexyl -5- oxo -3,5- dihydrobenzo [e] [1,4] oxygen azepine -3- formyl
The method of amine, including following experimental procedure：
Adjacent triazobenzene formic acid 1 (0.16g, 1mmol) is weighed, parabromoacetophenone aldehyde 2 (0.21g, 1mmol) and hexamethylene are weighed
Base isonitrile 3 (0.11g, 1mmol) is added in 5ml methylene chloride, is placed in and is reacted at room temperature 24 hours, that is, produces triazobenzene
Carbamate derivatives；Reaction solution without isolation, is added triphenylphosphine (3.15g, 1.2mmol), occurs under triphenyl phosphine catalyst
Intramolecular wittig reaction；Column chromatographic isolation and purification, which is carried out, through silicagel column after the reaction was completed obtains target compound 4d：
Elemental analysis：59.96 H% of measured value C%, 4.91 N% 6.54
59.87 H% of calculated value C%, 4.80 N% 6.35
1H NMR(CDCl3, 600MHz) and δ (ppm) 7.98 (d, J=7.8Hz, 1H, Ar-H), 7.71-7.56 (m, 5H, Ar-
H),7.46-7.39(m,2H,Ar-H),6.90(s,1H,NH),5.24(s,1H,CH),3.79(s,1H,CH),1.95-1.73
(m,4H,CH2),1.34-1.20(m,6H,CH2).
HRMS Calculatedfor[C22H21BrN2O3+H]+:441.0814,Found:441.0856.
Embodiment 5
A kind of synthesis (4- bromophenyl) -8- chloro- N- (4- chlorphenyl) -5- oxo -3,5- dihydrobenzo [e] [1,4] oxygen nitrogen
The method of miscellaneous -3- formamide, including following experimental procedure：
Weigh to chlorine neighbour's triazobenzene formic acid 1 (0.20g, 1mmol), weigh parabromoacetophenone aldehyde 2 (0.21g, 1mmol) and
Rubigan isonitrile 3 (0.14g, 1mmol) is added in 5ml methylene chloride, is placed in and is reacted at room temperature 24 hours, that is, produces folded
Benzaminic acid ester derivant；Reaction solution without isolation, is added triphenylphosphine (3.15g, 1.2mmol), in triphenyl phosphine catalyst
Issue raw intramolecular wittig reaction；Column chromatographic isolation and purification, which is carried out, through silicagel column after the reaction was completed obtains target compound 4d：
Elemental analysis：52.75 H% of measured value C%, 2.81 N% 5.70
52.41 H% of calculated value C%, 2.60 N% 5.56
1H NMR(CDCl3, 600MHz) and δ (ppm) 8.20 (s, 1H, Ar-H), 8.07 (d, J=8.0Hz, 2H, Ar-H),
7.96 (d, J=8.0Hz, 1H, Ar-H), 7.67 (d, J=8.4Hz, 2H, Ar-H), 7.49 (d, J=8.4Hz, 2H, Ar-H),
7.34 (t, J=8.0Hz, 1H, Ar-H), 6.73-6.67 (m, 2H, Ar-H), 6.54 (s, 1H, NH), 5.68 (s, 1H, CH)
.HRMS Calculatedfor[C22H13BrCl2N2O3+H]+:502.9565,Found:502.9588.
Embodiment 6
A kind of synthesizing methyl (2- (4- bromophenyl) -5- oxo -3,5- dihydrobenzo [e] [1,4] oxygen azepine -3- carbonyl) is sweet
The method of propylhomoserin ethyl ester, including following experimental procedure：
Adjacent triazobenzene formic acid 1 (0.16g, 1mmol) is weighed, methyl acetophenone aldehyde 2 (0.15g, 1mmol) and acetic acid are weighed
Carbomethoxy isonitrile 3 (0.10g, 1mmol) is added in 5ml methylene chloride, is placed in and is reacted at room temperature 24 hours, that is, produces nitrine
Yl benzoic acid ester derivant；Reaction solution without isolation, is added triphenylphosphine (3.15g, 1.2mmol), under triphenyl phosphine catalyst
Intramolecular wittig reaction occurs；Column chromatographic isolation and purification, which is carried out, through silicagel column after the reaction was completed obtains target compound 4d：
Elemental analysis：65.86 H% of measured value C%, 5.10 N% 7.77
65.57 H% of calculated value C%, 4.95 N% 7.65
1H NMR(CDCl3, 400MHz) and δ (ppm) 7.98 (d, J=8.0Hz, 1H, Ar-H), 7.76 (d, J=7.6Hz, 2H,
), Ar-H 7.69 (t, J=7.6Hz, 1H, NH), 7.46 (d, J=8.4Hz, 2H, Ar-H), 7.38 (t, J=7.6Hz, 1H, Ar-
), H 7.25 (d, J=8.4Hz, 2H, Ar-H), 5.37 (s, 1H, CH), 4.17-3.99 (m, 2H, CH2),3.77(s,3H,CH3),
2.39(s,3H,CH3).
HRMS Calculatedfor[C20H18N2O5+H]+:367.1294,Found:367.1266.
The biological activity test of target compound benzo oxygen azatropylidene 4
Equipment and material：
Desk-top high-pressure high-temperature steam sterilization case (YXQ.DY type), the electronic balance (Sartorius of sensibility reciprocal a ten thousandth
BT25S), aseptic operating platform (will is sincere, ZHJH-C1109B), transfer needle, glass bar, graduated scale, lighter, sealed membrane, triangular flask
(75mL), graduated cylinder (20mL), microsyringe (100 μ L, 200 μ L, 500 μ L, 1000 μ L), culture dish (diameter 6cm), mould training
It supports case (MJX-250 type), crocus cloth, alcolhol burner, diameter 5mm punch.
PDA powder (Qingdao Haiyang chemical industry), distilled water, DMSO, Tween-80, gibberella saubinetii
(Gibberellasaubinetii), rice blast fungus (Magnaporthegrisea), penicillium digitatum (Penicillium
Digitatum), penicillium italicum (Penicillium italicum), Rhizoctonia solani (Rhizoctonia solani).
Experimental method (using toxic medium method is contained)
The preparation of PDA culture medium
PDA powder 46g is weighed, distilled water 1000mL is added, shakes up and is configured to solution, cover bottleneck with cotton gauze.This is trained
Feeding base is put into high-pressure sterilizing pot to be sterilized 0.5h using wet heating at 125 DEG C.
5.7.2.2 the preparation (50mg/L) of sample
2~3mg sample to be tested is weighed with assay balance to be put in the sample cell sterilized, and a few drop DMSO are added and dissolve the sample
Product are added appropriate distilled water and a drop Tween-80, are configured to the solution that uniform concentration is 1000mg/L, take 1000 μ of this solution
L is quickly adding into (40~50 DEG C) culture medium of 9.0mL heat, shakes up the training for being configured to that sample to be tested concentration is 100mg/L
Base is supported, ultraviolet-sterilization 15min in aseptic operating platform is lain in a horizontal plane in.
5.7.2.3 Antibacterial Activity
Strain agar block is taken with diameter 5mm punch, mycelia is inoculated with down will be containing the PDA culture medium of candidate drug
On, it is placed in the center of round culture medium, cutting not slide strain agar block, in order to avoid pollution culture medium.Each sample to be tested connects
Kind three is to blank photo, with the commodity chemical drug containing same concentrations with the culture medium without drug but containing same concentrations DMSO
The conduct control of object olefin conversion, triazolone, is placed on after cultivating 3~5 days at 25 DEG C in biochemical cultivation case, measures on culture medium
Bacterium colony diameter.Sample to be tested is observed to bacterium by the comparison with above-mentioned blank control group and commercial pharmaceutical control group
The influence of silk growth calculates sample to be tested at 100mg/L to the inhibiting rate of bacterium colony growth.
Inhibiting rate (%)=[(blank control colony diameter-sample to be tested colony diameter)/(blank colony diameter-punching
Device diameter)] × 100%
The bacteriostatic activity test result of target compound benzo oxygen azatropylidene 4
Table 1：The bacteriostatic activity test result of compound 4
Note：Compound concentration is 50mg/L；Data are duplicate average value three times.
As can be seen from the above Table 1, the compound of the present invention Isosorbide-5-Nitrae-Benzoxazepin is at 100mg/L to rice banded sclerotial blight
Bacterium (Rhizoctonia solani), penicillium digitatum (Penicillium digitatum), penicillium italicum
(Penicillium italicum) shows preferable bacteriostatic activity.It is wherein best with compound 4e effect.
The compound of the present invention is as fungicide in use, the load that can will allow in the compound of the present invention and other plant protection
Body or diluent mixing, are modulated into usually used various dosage forms, such as mixture, granule, aqueous emulsion whereby to use,
It can also be used in mixed way or be used in combination simultaneously with other pesticides such as fungicide, Insecticides (tech) & Herbicides (tech) and plant growth regulator.
Claims (4)
1. a kind of benzo oxygen azatropylidene class bacteriostatic agent, which is characterized in that the chemical structural formula of the bacteriostatic agent is：
Wherein, substituent R1、R2And R3For chloro or bromo or methyl or normal-butyl or rubigan or methyl acetate base or tertiary fourth
Base or cyclohexyl.
2. the method for synthesizing benzo oxygen azatropylidene class bacteriostatic agent described in claim 1, which is characterized in that the method includes with
Lower synthesis path：
(1) under room temperature, adjacent triazobenzene formic acid derivates are added into reaction flask, weighs aryl keto-aldehyde and isonitrile is added to
In methanol；
(2) reaction system in the step (1) is placed in and is reacted at room temperature 4-12 hours, that is, produce triazobenzene formic acid esters
Derivative；
(3) reaction solution for taking the step (2) without isolation, issues raw intramolecular wittig reaction in triphenyl phosphine catalyst；It is surplus
Excess carries out column chromatographic isolation and purification through silicagel column and obtains target compound；
Complete the synthesis of benzo oxygen azatropylidene class bacteriostatic agent.
3. according to the method described in claim 2, it is characterized in that：The adjacent triazobenzene formic acid derivates of the step (1), aryl
The molar feed ratio of keto-aldehyde and isonitrile is 1:1:1.
4. benzo oxygen azatropylidene class bacteriostatic agent described in claim 1 as gibberella saubinetii, rice blast fungus, penicillium italicum,
Penicillium digitatum, Rhizoctonia solani fungicide on application.
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| 1,5-苯并二氮杂卓内酯类化合物的合成及抑菌活性研究;安晓然;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20160916(第10期);第B014-49页 * |
| 2-位酯基取代-1，5-苯并氧氮杂卓衍生物的合成、抑菌活性及γ-丁內酯酯交换反应的研究;赵利飞;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20150815(第8期);第B014-61页 * |
| Two new compounds from marine-derived fungus Penicillium sp. F11;P. Zhuang et al.;《Journal of Asian Natural Products Research》;20120331;第14卷(第3期);第197-203页 * |
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