CN104356062A - Preparation method of p-hydroxybenzaldehyde condensed isoniazide and application thereof - Google Patents
Preparation method of p-hydroxybenzaldehyde condensed isoniazide and application thereof Download PDFInfo
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- CN104356062A CN104356062A CN201410564617.6A CN201410564617A CN104356062A CN 104356062 A CN104356062 A CN 104356062A CN 201410564617 A CN201410564617 A CN 201410564617A CN 104356062 A CN104356062 A CN 104356062A
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- hydroxybenzaldehyde
- vazadrine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/88—Nicotinoylhydrazones
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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Abstract
The invention discloses a preparation method of p-hydroxybenzaldehyde condensed isoniazide and application thereof, and belongs to the field of plant disease control. According to the method, p-hydroxybenzaldehyde condensed isoniazide is utilized to research the inhibitory effect on cucumber damping-off fungi and phyricularia grisea by p-hydroxybenzaldehyde condensed isoniazide through a mycelial growth rate method. Agent concentration is set to be five gradients which are 1 microgram/ml, 2 microgram/ml, 4 microgram/ml, 6 microgram/ml and 8 microgram/ml to perform tests, the bacterial colony inhibitory effect is measured through the growth rate method, and the median lethal concentration EC50 and inhibition ratio of germs are obtained by processing diameter data of the bacterial colony. Being contrasted from the point of the EC50 value, the sensitive degree of germs on p-hydroxybenzaldehyde condensed isoniazide is cucumber damping-off fungi and phyricularia grisea. Experimental results show that p-hydroxybenzaldehyde condensed isoniazide has an inhibitory effect on both cucumber damping-off fungi and phyricularia grisea, wherein the inhibitory effect on cucumber damping-off fungi is the best.
Description
Technical field
The invention belongs to field of plant disease control, particularly a kind of preparation method of p-Hydroxybenzaldehyde contracting vazadrine and application thereof.
Background technology
Cucumber samping off occurs in seedling stage, is world-renowned destructive disease.This germ strong adaptability, harm weigh, and cause very large loss to Vegetable produce for a long time, general nursery sickness rate is 20-50%, and serious reaches more than 80%.For cucumber samping off, scientific research personnel has carried out large quantity research.From domestic and foreign literature report, find that beneficial agents has metaxanin, fenaminosulf, Difolatan, second manganese, metalaxyl, hymexazol etc., in production, main metaxanin seed dressing and the soil of adopting processes cucumber at seedling stage samping off, but due to drug-fast generation, calendar year 2001 just has report metaxanin to prevent and treat failed example, in the urgent need to the new medicament of control cucumber at seedling stage samping off in therefore producing.
Rice blast, in the Exploitation of the Works of Nature of SONG Yingxing work in 1637, is called as " inflammation fire ".It and bacterial leaf spot and banded sclerotial blight are listed as the large Major Diseases of paddy rice three.Rice blast, due to its popularity occurred and destructiveness, brings huge loss to grain-production.Along with the expansion of paddy field area, disadvantageous weather condition and irrational cultivation step etc., make the harm of rice blast increase the weight of year by year.Since the nineties in 20th century, China's rice blast year occurring area all at 3,800,000 hm
2above, year loss paddy reaches several hundred million kilograms.Within 2005, Guangxi District occurring area is more than 66.67 ten thousand hm
2, grain drop in production 7.68 hundred million kilograms, financial loss reaches 12.5 hundred million yuan.There is generation rice blast in each paddy rice producing region, the whole nation, especially occurs heavy with mountain area, knob, as long as condition is suitable for, easily popularly to cause disaster, the general underproduction 10% ~ 20% of popular time, the heavy underproduction 40% ~ 50%, even No kernels or seeds are gathered, as in a year of scarcity.Mainly contain for the medicament preventing and treating Pyricularia oryzae at present: tricyclazole, Fujione, Kitazine, iprobenfos and Hinosan etc.But because onset area is large, be in a bad way, the antiseptic-germicide kind of use is few, and Pyricularia oryzae has developed immunity to drugs to most disinfectant use in agriculture.
In current chemical pesticide, antibacterial kind is single, also brings the series of problems such as environmental pollution and resistance simultaneously.So, in the urgent need to developing pharmaceutical preparations, and be used alternatingly the different medicament of the mechanism of action as much as possible, to alleviate the development of germ resistance problems.
Summary of the invention
For overcoming the shortcoming and deficiency that exist in prior art, primary and foremost purpose of the present invention is the preparation method providing a kind of p-Hydroxybenzaldehyde contracting vazadrine.
Another object of the present invention is to the p-Hydroxybenzaldehyde contracting vazadrine providing aforesaid method to prepare.
Another object of the present invention is the application of p-Hydroxybenzaldehyde contracting vazadrine in controlling plant diseases providing above-mentioned acquisition.
Object of the present invention is achieved through the following technical solutions: a kind of preparation method of p-Hydroxybenzaldehyde contracting vazadrine, specifically comprises the following steps:
Being joined the 10mmol vazadrine weighed up fills in the 100ml three-necked flask of 10ml dehydrated alcohol in advance, makes it to dissolve at temperature constant magnetic stirring water-bath constant temperature 65 DEG C of stirring and refluxing 10min; The p-Hydroxybenzaldehyde separately taking 10mmol is placed in 50ml beaker, and the mouth of pipe from three-necked flask after adding 10ml anhydrous alcohol solution dropwise adds in three-necked flask; Solution becomes clarification after first becoming muddiness, has pale yellow precipitate to separate out after 10min, continues backflow 4.5h, solution is cooled to room temperature, filter, obtain faint yellow fine powdered solid, carry out recrystallization with dehydrated alcohol, namely obtain p-Hydroxybenzaldehyde contracting vazadrine.
The building-up reactions formula of above-mentioned p-Hydroxybenzaldehyde contracting vazadrine is such as formula shown in I:
A kind of p-Hydroxybenzaldehyde contracting vazadrine is prepared by aforesaid method.The molecular structure of described p-Hydroxybenzaldehyde contracting vazadrine as shown in Figure 1.
The p-Hydroxybenzaldehyde contracting vazadrine of above-mentioned acquisition is applied in the control of cucumber samping off.
The p-Hydroxybenzaldehyde contracting vazadrine of above-mentioned acquisition is applied in the control of rice blast.
The present invention has following advantage and effect relative to prior art:
The present invention tests proof, the germ that the medicament p-Hydroxybenzaldehyde contracting vazadrine of new synthesis is corresponding to rice blast, tomato late childbirth disease and cucumber samping off has good restraining effect, inhibition particularly for Cucumber damping-off is best, and the p-Hydroxybenzaldehyde contracting vazadrine in the present invention can well be applied in the control of rice blast and cucumber samping off.
Accompanying drawing explanation
Fig. 1 is the molecular structure of p-Hydroxybenzaldehyde contracting vazadrine.
Fig. 2 is the structure cell accumulation graph of p-Hydroxybenzaldehyde contracting vazadrine.
Fig. 3 is that after cultivating 7d, p-Hydroxybenzaldehyde contracting vazadrine is on the impact of Cucumber damping-off mycelial growth, and wherein, a is contrast, and colony diameter is 2.3299 ㎝; B concentration is 1 μ g/mL, and colony diameter is 2.0102 ㎝; C concentration is 2 μ g/mL, and colony diameter is 1.9857 ㎝; D concentration is 4 μ g/mL, and colony diameter is 1.7493 ㎝; E concentration is 6 μ g/mL, and colony diameter is 1.7497 ㎝; F concentration is 8 μ g/mL, and colony diameter is 1.5883 ㎝.
Fig. 4 p-Hydroxybenzaldehyde contracting vazadrine on the impact of rice Pyricularia grisea mycelial growth, wherein: a for contrast, bacterium cake diameter is 2.3299 ㎝; B concentration is 1 μ g/mL, and colony diameter is 2.238 ㎝; C concentration is 2 μ g/mL, and colony diameter is 1.767 ㎝; D concentration is 4 μ g/mL, and colony diameter is 1.741 ㎝; E concentration is 6 μ g/mL, and bacterium cake diameter is 1.718 ㎝; F concentration is 8 μ g/mL, and bacterium cake diameter is 1.669 ㎝.
Fig. 5 p-Hydroxybenzaldehyde contracting vazadrine is to paddy rice sick Pyricularia oryzae toxicity test regression curve.
Fig. 6 p-Hydroxybenzaldehyde contracting vazadrine is to Cucumber damping-off toxicity test regression curve.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
Embodiment 1
One, the synthesis of p-Hydroxybenzaldehyde contracting vazadrine and structure are determined
1. the synthesis of p-Hydroxybenzaldehyde contracting vazadrine
Being joined the 10mmol weighed up (about 1.3714g) vazadrine fills in the 100ml three-necked flask of 10ml dehydrated alcohol in advance, makes it to dissolve at HJ-3 temperature constant magnetic stirring water-bath constant temperature 65 DEG C of stirring and refluxing 10min; The p-Hydroxybenzaldehyde separately taking equimolar amount 10mmol (about 1.2212g) is placed in 50ml beaker, and the mouth of pipe from three-necked flask after adding 10ml anhydrous alcohol solution dropwise adds in three-necked flask; Solution becomes clarification after first becoming muddiness, has pale yellow precipitate to separate out after 10min, continues backflow 4.5h, solution is cooled to room temperature, filters, obtain faint yellow fine powdered solid, carry out recrystallization with dehydrated alcohol, products therefrom is p-Hydroxybenzaldehyde contracting vazadrine.The building-up reactions formula of above-mentioned p-Hydroxybenzaldehyde contracting vazadrine is such as formula shown in I:
2. the cultivation of p-Hydroxybenzaldehyde contracting vazadrine monocrystalline
Take the product of the above-mentioned Reactive Synthesis of 0.2mmol, be placed in the reactor that 9ml methyl alcohol is housed, be placed on after stirring in electric drying oven with forced convection, in 80 DEG C of isothermal reaction 48h, hold over night after electric drying oven with forced convection temperature being down to 36 DEG C by lowering the temperature step by step, opens reactor for second day, yellow crystals is had to separate out in still, filter, naturally dry, obtain p-Hydroxybenzaldehyde contracting vazadrine monocrystalline.
3. the crystal structure determination of p-Hydroxybenzaldehyde contracting vazadrine
Choosing size is that the p-Hydroxybenzaldehyde contracting vazadrine monocrystalline of 0.570nm × 0.400nm × 0.300nm is installed on the glass fibers, is placed on (SMART APEX II) X-ray single crystal diffractometer, with graphite monochromatised MOK alpha-ray (
) radiation is light source, at 296 (2) K temperature, collect point diffraction, collect 2018 diffraction datas altogether, wherein 1758 is independent diffraction data.X-ray single crystal diffraction measures p-Hydroxybenzaldehyde contracting vazadrine monocrystalline crystallographic data, non-hydrogen atom coordinate, thermal parameter and crystalline structure, closest packing respectively in table 1, table 2, table 3 and Fig. 1, Fig. 2.Known by test result, schiff bases crystal belongs to oblique system, P21/c spacer.
The partial crystals data of table 1 p-Hydroxybenzaldehyde contracting vazadrine crystal
aR
1＝Σ||F
o|–|F
c||/Σ|F
o|.
bwR
2＝[Σw(F
o 2–F
c 2)
2/Σw(F
o 2)
2]
1/2.
Non-hydrogen atom coordinate (× 10 in table 2 p-Hydroxybenzaldehyde contracting vazadrine
4) and thermal parameter (A
2× 10
3)
The main bond distance of table 3 p-Hydroxybenzaldehyde contracting vazadrine and bond angle
Two, the applying detection of p-Hydroxybenzaldehyde contracting vazadrine
1. experimental strain
Cucumber damping-off (Bythium deliense Meurs) (provided by Shanghai academy of agricultural sciences ecology);
Rice blast fungus (Magnaporthe grisea, M.grisea) (is provided by Hunan agricultural university Biosafety technical college; Wu Zhihua, rice blast fungus to the preliminary study [D] of the resistant determination of six kinds of sterilant and anti-isoprothiolane mechanism, 2011, Agricultural University Of Hunan, Chinese large Ph D dissertation full-text database in 2011)
Acetone (content >=99.5% analytical pure, Chengdu Ke Long chemical reagent factory produces);
Electro-heating standing-temperature cultivator (model: HH.B11600-S-II, Shanghai leap medical apparatus and instruments factory), Bechtop (model: SW-CJ-2FD), high-pressure sterilizing pot (model: Canon.PowerShot A650 IS)
2 experimental techniques
The preparation of 2.1 substratum
PDA substratum (potato dextrose agar) (1000mL): potato 200g, sucrose 20g, agar 15g; Peeling potatoes cuts fritter, boils 30min, with filtered through gauze sugaring and agar again, supplies water to 1000mL after dissolving; Packing, for subsequent use after 121 DEG C of autoclaving 30min.
The isolation and purification of 2.2 pathogenic fungies
The Cucumber damping-off strain, the rice blast fungi isolates that supply examination in Bechtop, first streak inoculation on PDA substratum in culture dish, at being placed in 30 DEG C, after constant temperature culture 5 ~ 7d, picking inoculates purifying again containing bacterium sample, repeats 2 ~ 3 times, obtains purebred for trying bacterium.
2.3 pastille substratum configurations
With acetone as solvent, take acetone as blank, reagent agent is dissolved in acetone, be mixed with the p-Hydroxybenzaldehyde contracting vazadrine sample mother liquor that concentration is 0.1mg/mL, by the mother liquor prepared and substratum according to 1: 100 volume ratio join in the PDA substratum melted, the diameter pouring sterilizing after mixing into is in the culture dish of 90mm, makes the pastille culture medium flat plate of substratum containing reagent agent and reagent agent series concentration gradient (1 μ g/mL, 2 μ g/mL, 4 μ g/mL, 6 μ g/mL, 8 μ g/mL).
2.4 measure project
Mycelial growth rate is adopted to suppress method; Be that the punch tool of 1.00cm is beaten and got bacterium cake on above-mentioned cultured bacterium colony with diameter, then bacterium cake shifted, be upside down on the culture medium flat plate of above-mentioned pastille.Every plating 3 ferfas cake, the arrangement in " product " font, each concentration of often kind of medicament is 1 process, often processes 3 times and repeats, and cultivates 7 days for 30 DEG C, and the bacterium colony measuring each process with " ten " word interior extrapolation increases diameter.
Bacterium colony increases diameter (cm)=colony growth diameter-1.00 (bacterium cake diameter)
Calculate medicament as follows to the inhibiting rate of mycelial growth.
2.5 data processing
Utilize Excel form, mycelial growth inhibition rate is converted to probability value (y), drug concentration (μ g/mL) converts denary logarithm value (x) to, do regression straight line, obtain virulence regression equation (y=a+bx) and relation conefficient (r), calculate the 50 1.143851e-144ffective concentration (EC that p-Hydroxybenzaldehyde contracting vazadrine suppresses rice blast fungus mycelial growth
50), EC
50value is carried out medicament virulence size and is compared, and represents that p-Hydroxybenzaldehyde contracting vazadrine is to the inhibiting power of Pyricularia oryzae with this.
SPSS17.0 statistical software is utilized to carry out whether there are differences significance between one-way analysis of variance inspection different treatment.
3 experimental results and analysis
3.1 p-Hydroxybenzaldehyde contracting vazadrine are to the restraining effect of two kinds of germ mycelial growths
As shown in Figure 3, for cultivating after 7 days mycelial growth situation under each concentration, along with the increase of drug concentration, Cucumber damping-off colony diameter reduces.What colony diameter was maximum is control group, and after cultivating 7d, colony diameter reaches 2.33cm, and 8 μ g/mL treatment group are less by 126.06% than the diameter of control group 0 μ g/mL.
As shown in Figure 4, rice blast colony diameter reduces along with the increase of drug concentration the upgrowth situation of the rice blast fungus bacterium colony under different concns process.All process obvious difference compared with the control, when concentration is 8 μ g/mL, bacterium colony increases diameter is 0.669 ㎝, than increment (1.3299 ㎝) little 0.653 ㎝ of control group 0 μ g/mL and little by 50.03%.2 μ g/mL treatment group bacterium colonies increase diameters than little 0.471 ㎝ of 1 μ g/mL group (1.238 ㎝).Concentration 8 μ g/mL inhibition is best.
3.2 p-Hydroxybenzaldehyde contracting vazadrine are to the inhibiting rate of two kinds of germ mycelial growths
The inhibiting rate of p-Hydroxybenzaldehyde contracting vazadrine to Cucumber damping-off and rice blast fungus mycelial growth is shown in Table 4:
Table 4 p-Hydroxybenzaldehyde contracting vazadrine is to the inhibiting rate of two kinds of germ mycelial growths
Note: capitalization represents that between process, difference extremely significantly (P < 0.01); Lowercase represents significant difference between process (P < 0.05).
Can be obtained by table 4, in p-Hydroxybenzaldehyde contracting vazadrine in the restraining effect of cucumber samping off germ, concentration is that 8 μ g/mL process inhibiting rates are the highest, remarkable with other concentration difference heteropoles; Show the inhibition test result of Pyricularia oryzae, 8 μ g/mL process inhibiting rates are nearly 50%, and remarkable with other concentration difference heteropoles, 1 μ g/mL treatment effect is poor, reaches pole significant difference with other concentration.
In sum, all there is restraining effect p-Hydroxybenzaldehyde contracting vazadrine to Cucumber damping-off, rice blast fungus, and the higher then inhibition of concentration is better.From the inhibiting rate of two kinds of germs, the effect of p-Hydroxybenzaldehyde contracting vazadrine to Cucumber damping-off is better than the effect to rice blast.
3.3 p-Hydroxybenzaldehyde contracting vazadrine are to the toxicity test of germ indoor
Hydroxy benzaldehyde contracting vazadrine the results are shown in Table shown in 5 to cucumber samping off germ, tomato late blight and rice Pyricularia grisea Toxicity Determination:
Table 5 p-Hydroxybenzaldehyde contracting vazadrine is to two kinds of germ Toxicity Determination results
Medicament EC
50the size of value weighs the important indicator of medicament virulence size, EC
50value is less shows that the virulence of this medicament is stronger.P-Hydroxybenzaldehyde contracting vazadrine suppresses EC to Cucumber damping-off as shown in Table 5
50value is 0.829; EC is suppressed to rice blast fungus
50value is 7.598.Then in these two kinds of bacterium, the suppression sterilization effect of p-Hydroxybenzaldehyde contracting vazadrine to Cucumber damping-off is better than rice blast fungus.
The drafting of 3.4 p-Hydroxybenzaldehyde contracting vazadrine toxicity regression curves
According to the data in table 5, take the logarithm as X-coordinate respectively to each chemicals treatment concentration, suppress probability value to be ordinate zou, draw the toxicity regression curve of germ respectively, see Fig. 5 and Fig. 6.
4 conclusions and discussion
This experiment is the test that research p-Hydroxybenzaldehyde contracting vazadrine medicament is prevented and treated rice blast and Cucumber damping-off.Result shows: there is certain restraining effect p-Hydroxybenzaldehyde contracting vazadrine to the two kind of plant pathogenic fungies for examination, and along with the increase of medicament working concentration, reagent agent improves the fungistatic effect of germ.The results show, the inhibition of reagent agent to cucumber samping off is better than rice blast.
Above-described embodiment is the present invention's preferably embodiment; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from spirit of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (4)
1. a preparation method for p-Hydroxybenzaldehyde contracting vazadrine, is characterized in that, specifically comprises the following steps:
Being joined the 10mmol vazadrine weighed up fills in the 100ml three-necked flask of 10ml dehydrated alcohol in advance, makes it to dissolve at temperature constant magnetic stirring water-bath constant temperature 65 DEG C of stirring and refluxing 10min; The p-Hydroxybenzaldehyde separately taking 10mmol is placed in 50ml beaker, and the mouth of pipe from three-necked flask after adding 10ml anhydrous alcohol solution dropwise adds in three-necked flask; Solution becomes clarification after first becoming muddiness, has pale yellow precipitate to separate out after 10min, continues backflow 4.5h, solution is cooled to room temperature, filter, obtain faint yellow fine powdered solid, carry out recrystallization with dehydrated alcohol, namely obtain p-Hydroxybenzaldehyde contracting vazadrine.
2. a p-Hydroxybenzaldehyde contracting vazadrine is prepared by method according to claim 1.
3. p-Hydroxybenzaldehyde contracting vazadrine according to claim 2 is applied in the control of cucumber samping off.
4. p-Hydroxybenzaldehyde contracting vazadrine according to claim 2 is applied in the control of rice blast.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4100290A (en) * | 1975-05-14 | 1978-07-11 | Ciba-Geigy Corporation | Pyridine-4-carboxylic acid hydrazones for combatting phytopathogenic microorganisms |
| GB2325932A (en) * | 1997-06-04 | 1998-12-09 | Bayer Agrochem Kk | Isonicotinic Acid Hydrazide Derivatives |
-
2014
- 2014-10-22 CN CN201410564617.6A patent/CN104356062A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4100290A (en) * | 1975-05-14 | 1978-07-11 | Ciba-Geigy Corporation | Pyridine-4-carboxylic acid hydrazones for combatting phytopathogenic microorganisms |
| GB2325932A (en) * | 1997-06-04 | 1998-12-09 | Bayer Agrochem Kk | Isonicotinic Acid Hydrazide Derivatives |
Non-Patent Citations (4)
| Title |
|---|
| HITESH KUMAR，ET AL.: "Synthesis, Characterization and Evaluation of Isoniazid Analogues as Potent Anticancer Agents", 《PHARMACOLOGYONLINE》 * |
| MARCELLE DE L. FERREIRA，ET AL.: "Synthesis and Antitubercular Evaluation of N"-[(E)-(hydroxy,methoxy and ethoxy-substituted-phenyl) Methylidene]isonicotinohydrazide Derivatives", 《LETTERS IN DRUG DESIGN & DISCOVERY》 * |
| QI-LIANG DENG，ET AL.: "N’-(4-Hydroxybenzylidene)isonicotinohydrazide", 《ACTA CRYSTALLOGRAPHICA SECTION E》 * |
| S. RAMACHANDRAN，ET AL.: "SYNTHESIS & ANTI- MICROBIAL EVALUATION OF N-(2-(4-SUBSTITUTED PHENYL)-4-OXOTHIAZOLIDIN-3-YL) ISONICOTINAMIDE DERIVATIVES", 《INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH》 * |
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