CN103626748A - Oxadiazole compound containing pyridine, and preparation method and application of oxadiazole compound containing pyridine - Google Patents

Oxadiazole compound containing pyridine, and preparation method and application of oxadiazole compound containing pyridine Download PDF

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CN103626748A
CN103626748A CN201310663884.4A CN201310663884A CN103626748A CN 103626748 A CN103626748 A CN 103626748A CN 201310663884 A CN201310663884 A CN 201310663884A CN 103626748 A CN103626748 A CN 103626748A
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formula
compound
phenyl
containing pyridine
oxadiazole
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CN103626748B (en
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刘幸海
孙召慧
杨明艳
谭成侠
翁建全
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Guangdong Gaohang Intellectual Property Operation Co ltd
Nantong Xinyong Textile Technology Co ltd
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Zhejiang University of Technology ZJUT
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/72—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
    • A01N43/82—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 five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention discloses an oxadiazole compound containing pyridine, a preparation method of the oxadiazole compound containing pyridine and application of the oxadiazole compound containing pyridine in prevention and control of tomato bacterial speck, cucumber fusarium wilt and botrytis cinerea, wherein the compound is shown in a formula (I). The compound provided by the invention is a new compound with bactericidal activity and provides a base for research and development of new pesticides. The formula (I) is shown in the specification.

Description

A kind of containing pyridine oxadiazole compounds and preparation and application thereof
Technical field
The present invention relates to a kind of is 2-(4-pyridin-2-yl-)-5-(substituted alkane sulphur base)-1,3 containing pyridine oxadiazole compounds, 4-oxadiazole derivative and preparation and application thereof.
background technology
Heterogeneous ring compound has been the main flow of novel pesticide development, and in heterogeneous ring compound, take again nitrogen heterocyclic ring as main.1,3,4-oxadiazole compounds also has very important biological activity, comprises anti-inflammatory, anticancer, antiviral, bacteriostasis and herbicides isoreactivity.As synthetic 2-substituted pyrazolecarboxylic-5-methylthio group-1,3,4-oxadiazole shows good inhibition activity to Rhizoctonia solani Kuhn when 100 mg/L; 2-methyl-5-replaces benzylthio--1, and 3,4-oxadiazole has good inhibition to rape under 100ppm.
Yet, there is not yet relevant 2-(4-pyridin-2-yl-)-5-(substituted alkane sulphur base)-1,3, the bibliographical information of the synthetic and bioactivity research of 4-oxadiazole derivative.
Summary of the invention
The object of the invention is to provide a kind of 2-(4-pyridin-2-yl-)-5-(substituted alkane sulphur base)-1,3 with fungicidal activity, 4-oxadiazole derivative and preparation method thereof and application.
The object of the present invention is achieved like this:
Shown in formula (I) containing pyridine oxadiazole compounds:
Figure 2013106638844100002DEST_PATH_IMAGE001
（I）
In formula (I): R is C1-C6 alkyl, C1-C6 carbalkoxy, C2-C6 thiazolinyl, the optional phenyl replacing, optional 5 yuan or 6 yuan of heteroaryls that replace, and described replacement is selected from one or more hydrogen, C1-C6 alkyl, C1-C6 alkoxyl group, C1-C6 alkylthio, cyano group, halogen.
Formula of the present invention (I) compound can make by the following method: formula (II) compound and formula (III) compound are mixed with organic solvent, under the existence of alkaline matter, 0 ~ 25 ℃ of (preferably 25 ℃) stirring reaction, TLC follows the tracks of reaction, and (sherwood oil and the ethyl acetate mixture of volume ratio 1:1 ~ 5 of take is developping agent, following the tracks of raw material point disappears for reacting completely), after reacting completely, reaction solution is placed in to frozen water, separate out solid, filter, filtrate is carried out silica gel column chromatography, and (sherwood oil that the volume ratio of take is 5:1 and ethyl acetate mixture are eluent, collect the elutriant containing target components, dry) or carry out recrystallization with recrystallization solvent, shown in acquisition formula (I) containing pyridine oxadiazole compounds,
Recrystallization solvent is one or more in sherwood oil, ethyl acetate, normal hexane or ethanol, preferably the mixing solutions of sherwood oil and ethyl acetate;
Organic solvent is one or more in DMF, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane or acetone, is preferably DMF (DMF);
Alkaline matter is one or more in salt of wormwood, sodium bicarbonate, sodium hydroxide, potassium hydroxide or sodium hydride, is preferably salt of wormwood;
The ratio of the amount of substance of formula (II) compound, formula (III) compound and alkaline matter is 1:1.0 ~ 1.5:1.0 ~ 1.5, is preferably 1:1.0:1.2; Organic solvent volumetric usage is counted 2-10ml/mmol with formula (II) compound amount of substance, preferably 4ml/mmol.
Figure 743282DEST_PATH_IMAGE002
In formula (I) and formula (III): as previously mentioned, X is halogen in the definition of R.
The present invention also provide shown in formula (I) containing the application of pyridine oxadiazole compound in preventing and treating bacterial spot of tomato, cucumber fusarium axysporum, graw mold of tomato.
The present invention also provides and contains the sterilant containing pyridine oxadiazole compound shown in formula (I), and it also comprises acceptable auxiliary agent at least one agricultural chemicals.
Compared with prior art, beneficial effect of the present invention is mainly reflected in: the invention provides a kind of its preparation method and application containing pyridine oxadiazole compounds and intermediate, this compound is the new compound with fungicidal activity, for the research and development of novel pesticide provide the foundation.
Embodiment
Below in conjunction with specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in this:
It is of the present invention that containing pyridine oxadiazole compounds (I), method is synthetic as follows:
In 25 mL round-bottomed flasks, add 2 mmol Compound I I, 2 mmol to replace the K of benzyl chloride, 8mL DMF and 2.4mmol 2cO 3, stirring at room, TLC detection reaction progress.After completion of the reaction, in reaction solution impouring 30mL frozen water, separate out solid, filter, precipitation, silica gel column chromatography, obtains solid product.
Embodiment 1
2-(4-pyridin-2-yl-)-5-(4-methoxybenzyl sulfenyl)-1,3,4-oxadiazole (1): productive rate 88%, fusing point 126-128 ℃; 1h NMR (CDCl 3, 400 MHz), d:3.77 (s, 3H, OMe), 4.50 (s, 2H, SCH 2), 6.84 (d, j=8.6Hz, 2H, ArH), 7.36 (d, j=8.6Hz, 2H, ArH), 7.82 (d, j=4.8Hz, 2H, Py), 8.77 (d, j=2.8Hz, 2H, Py).
Embodiment 2
2-(4-pyridin-2-yl-)-5-(2-fluorine benzylthio-)-1,3,4-oxadiazole (2): productive rate 84%, fusing point 119-122 ℃; 1h NMR (CDCl 3, 400 MHz), d:4.51 (s, 2H, SCH 2), 7.30 (s, 2H, ArH), 6.99-7.05 (m, 2H, ArH), 7.19-7.25 (m, 1H, ArH). 7.46-7.49 (m, 1H, Py), 7.83 (s, 2H, Py), 8.74 (s, 2H, Py).
Embodiment 3
2-(4-pyridin-2-yl-)-5-(4-tertiary butyl benzylthio-)-1,3,4-oxadiazole (3): productive rate 86%, fusing point 114-115 ?c; 1h NMR (CDCl 3, 400 MHz), d:1.31 (s, 9H, Bu), 4.55 (s, 2H, SCH 2), 7.30 (q, j=8.6Hz, 4H, ArH), 7.86 (d, j=5.7Hz, 2H, Py), 8.81 (d, j=5.3Hz, 2H, Py).
Embodiment 4
2-(4-pyridin-2-yl-)-5-(3-cyano group benzylthio-)-1,3,4-oxadiazole (4): productive rate 88%, fusing point 110-112 ℃; 1h NMR (CDCl 3, 400 MHz), d:4.57 (s, 2H, SCH 2), 7.47 (t, j=7.7Hz, 1H, ArH), 7.60 (d, j=7.7Hz, 1H, ArH), 7.76 (d, j=7.7Hz, 1H, ArH), 7.80 (s, 1H, ArH), 7.96 (s, 2H, Py), 8.84 (s, 2H, Py).
Embodiment 5
2-(4-pyridin-2-yl-)-5-(2-benzyl chloride sulfenyl)-1,3,4-oxadiazole (5): productive rate 85%, fusing point 86-88 ℃; 1h NMR (CDCl 3, 400 MHz), d:4.68 (s, 2H, SCH 2), 7.28-7.30 (m, 2H, ArH), 7.44 (d, j=8.4Hz, 1H, ArH), 7.67 (d, j=8.4Hz, 1H, ArH), 7.86 (d, j=5.9Hz, 2H, Py), 8.82 (d, j=5.7Hz, 2H, Py).
Embodiment 6
2-(4-pyridin-2-yl-)-5-(2-chloropyridine methylene sulfenyl)-1,3,4-oxadiazole (6): productive rate 87%, fusing point 141-143 ℃; 1h NMR (CDCl 3, 400 MHz), d:4.50 (s, 2H, SCH 2), 7.30 (d, j=8.2Hz, 1H, ArH), 7.82-7.85 (m, 3H, ArH), 8.50 (d, j=2.8Hz, 2H, Py), 8.88 (d, j=5.3Hz, 2H, Py).
Embodiment 7
2-(4-pyridin-2-yl-)-5-(4-cyano group benzylthio-)-1,3,4-oxadiazole (7): productive rate 90%, fusing point 178-180 ℃; 1h NMR (CDCl 3, 400 MHz), d:4.57 (s, 2H, SCH 2), 7.64 (q, j=8.3Hz, 4H, ArH), 7.78 (s, 2H, Py), 8.82 (s, 2H, Py).
Embodiment 8
2-(4-pyridin-2-yl-)-5-(ethoxycarbonyl methylene sulfenyl)-1,3,4-oxadiazole (8): productive rate 88%, fusing point 98-100 ℃; 1h NMR (CDCl 3, 400 MHz), d:1.31 (t, 3H, Me), 4.14 (s, 2H, SCH 2), 4.28 (q, 2H, CH 2), 7.87 (s, 2H, Py), 8.82 (s, 2H, Py).
Embodiment 9
Fungicidal activity test
Subjects: bacterial spot of tomato, cucumber fusarium axysporum, graw mold of tomato.
Test method: adopt pot experiment method.Respectively by cucumber seeds and tomato seeds after 50 ℃ of immersions, after vernalization, be seeded in pot for growing seedlings, wait to grow to 2 true leaves for test.
Medicament is prepared: for reagent: get it filled and be made into 100ppm, get 89 kinds of each 5mg of compound, add 10% POLYSORBATE 80 after adding acetone solution again, finally add water and fully dissolve.Because so 100ppm is 100mg/L amount of water=5mg*1000/100mg=50ml, so add the amount=50ml*1%=0.5ml(of acetone dissolves because of final content≤1% of organic solvent), so because the final content of tween is should have tween 0.05 ml in 0.1% 50 ml water, that is: should add 10% tween 0.05 ml.
Application method: in the experiment of bacterial spot of tomato and graw mold of tomato, when tomato seedling grows two compound leaves, with watering can by reagent agent with contrast medicament and evenly sprays in confession and try on plant.
In cucumber fusarium axysporum experiment, cucumber seeds is soaked in after respectively will processing 2h and inoculates processing.
Inoculation method:
Bacterial spot of tomato adopts the inoculation of bacteria suspension spray method: cultured bacterial spot of tomato bacterium is converted to distilled water diluting and become 3 * 107cfu/ml bacteria suspension, use watering can spray inoculation.After inoculation, moisturizing is cultivated.
Graw mold of tomato adopts plays mycelium inoculation inoculation: by filtered through gauze, liquid nutrient medium and bacterium piece are separated, with crusher, the bacterium piece of the substratum with a small amount of liquid is smashed, with the liquid nutrient medium having filtered, mix and be made into certain density solution with the bacterium piece of smashing again, and with spectrophotometric determination solution transmittance (λ=630nm, OD=9.8).
Cucumber fusarium axysporum adopts the inoculation of Baconic's method for soaking seed: will in PD substratum, use filtered through gauze mycelia by cultured cucumber fusarium axysporum, and regulate spore concentration to 1 * 106cfu/ml to soak seed.
After clear water is fully fallen ill, carry out state of an illness investigation, and calculate disease index and prevention effect.
Figure 535789DEST_PATH_IMAGE004
table 1the live body fungicidal activity of target compound
Compound Bacterial spot of tomato Cucumber fusarium axysporum Graw mold of tomato
1 54.76 64.44 31.11
2 55.36 68.89 16.67
3 18.15 62.59 18.89
4 76.19 67.78 25.56
5 59.52 71.11 15.00
6 63.10 66.67 31.11
7 77.38 60.00 15.56
8 82.54 48.89 41.11

Claims (5)

  1. Shown in formula (I) containing the oxadiazole compounds of pyridine,
    Figure 2013106638844100001DEST_PATH_IMAGE001
    In formula (I), R is C1-C6 alkyl, C1-C6 carbalkoxy, C2-C6 thiazolinyl, the optional phenyl replacing, optional 5 yuan or 6 yuan of heteroaryls that replace, and described replacement is selected from one or more hydrogen, C1-C6 alkyl, C1-C6 alkoxyl group, C1-C6 alkylthio, cyano group, halogen.
  2. 2. compound as claimed in claim 1, is characterized in that in described formula (I), R is 2-chloro-phenyl-, 3-cyano-phenyl, 2-fluorophenyl, 4-tert-butyl-phenyl, 4-cyano-phenyl, 4-p-methoxy-phenyl, 2-chloropyridine base or ethoxycarbonyl.
  3. 3. the method for the compound of preparation described in claim 1 or 2, it comprises the steps: formula (II) compound and formula III compound to mix with organic solvent, under the effect of alkaline matter, 0 ~ 25 ℃ of stirring reaction, TLC follows the tracks of reaction, after reacting completely, reaction solution is placed in to frozen water, separates out solid, filter, filter cake carries out silica gel column chromatography or carries out recrystallization with recrystallization solvent, shown in acquisition formula (I) containing pyridine oxadiazole compounds;
    Described recrystallization solvent is one or more in sherwood oil, ethyl acetate, normal hexane or ethanol;
    One or more in described organic solvent DMF, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane or acetone;
    Described alkaline matter is one or more in salt of wormwood, sodium bicarbonate, sodium hydroxide, potassium hydroxide or sodium hydride;
    The ratio of the amount of substance of formula (II) compound and formula (III) compound and alkaline matter is 1:1.0 ~ 1.5:1.0 ~ 1.5, and organic solvent volumetric usage is counted 2-10ml/mmol with the amount of substance of formula (II) compound;
    Figure 867177DEST_PATH_IMAGE002
    R in formula (I), (III) is as defined in claim 1 or 2, and X is halogen.
  4. 4. a compound as claimed in claim 1 or 2 is prevented and treated the application in bacterial spot of tomato, cucumber fusarium axysporum, graw mold of tomato sterilant in preparation.
  5. 5. sterilant, contains acceptable auxiliary agent on compound described in claim 1 or 2 and at least one agricultural chemicals.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104177350A (en) * 2014-07-28 2014-12-03 天津普茂科技发展有限公司 Bitriazole phenyl-substituted oxadiazole compound and preparation method and application thereof
CN107033134A (en) * 2017-05-03 2017-08-11 贵州大学 Bisamide class compound containing pyridiniujm and 1,3,4 oxadiazolyls and preparation method and application
CN108218848A (en) * 2018-01-22 2018-06-29 贵州大学 A kind of trifluoromethyl pyridine oxadiazoles（Ether）Analog derivative and its application
CN114989155A (en) * 2021-03-01 2022-09-02 河北农业大学 1,3, 4-oxadiazole thioether derivative and preparation method and application thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101914094A (en) * 2010-07-29 2010-12-15 南京大学 1,3,4-oxadiazole derivative, preparation method and application thereof in preparing antitumor drug
CN102079730A (en) * 2010-09-06 2011-06-01 贵州大学 Derivatives containing 2, 5-substituted heterocyclic radical sulphone and synthesis method and application thereof
WO2012051601A2 (en) * 2010-10-14 2012-04-19 Epiomed Therapeutics, Inc. Heteroarylthio compounds
WO2012065065A1 (en) * 2010-11-12 2012-05-18 Follica, Inc. Methods and compositions for modulating hair growth, wound healing and scar revision
CN102499247A (en) * 2011-10-17 2012-06-20 贵州大学 Oxadiazole sulfone compound for controlling bacterial crop diseases
WO2013007663A1 (en) * 2011-07-08 2013-01-17 Technische Universität Darmstadt 2-benzylsulfanyl[1,3,4]-oxadiazole derivatives, and medical use thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101914094A (en) * 2010-07-29 2010-12-15 南京大学 1,3,4-oxadiazole derivative, preparation method and application thereof in preparing antitumor drug
CN102079730A (en) * 2010-09-06 2011-06-01 贵州大学 Derivatives containing 2, 5-substituted heterocyclic radical sulphone and synthesis method and application thereof
WO2012051601A2 (en) * 2010-10-14 2012-04-19 Epiomed Therapeutics, Inc. Heteroarylthio compounds
WO2012065065A1 (en) * 2010-11-12 2012-05-18 Follica, Inc. Methods and compositions for modulating hair growth, wound healing and scar revision
WO2013007663A1 (en) * 2011-07-08 2013-01-17 Technische Universität Darmstadt 2-benzylsulfanyl[1,3,4]-oxadiazole derivatives, and medical use thereof
CN102499247A (en) * 2011-10-17 2012-06-20 贵州大学 Oxadiazole sulfone compound for controlling bacterial crop diseases

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
FABIO LO MONTE ET AL.: "Identification of Glycogen Synthase Kinase-3 Inhibitors with a Selective Sting for Glycogen Synthase Kinase-3α", 《J. MED. CHEM.》, vol. 55, 25 April 2012 (2012-04-25), XP029064992, DOI: 10.1016/j.jmgm.2014.06.013 *
FABIO LO MONTE: "Structure-bas ed optimization of oxadiazole-based GSK-3 inhibitors", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》, vol. 61, 12 June 2012 (2012-06-12), XP028991140, DOI: 10.1016/j.ejmech.2012.06.006 *
HACER BAYRAK ET AL.: "Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》, vol. 44, 28 May 2009 (2009-05-28) *
HACER BAYRAK ET AL.: "Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》, vol. 44, 28 May 2009 (2009-05-28), pages 4362 - 4366 *
KAI LIU, ET AL.: "Synthesis, molecular modeling and biological evaluation of 2-(benzylthio)-5-aryloxadiazole derivatives as anti-tumor agents", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》, vol. 47, 18 November 2011 (2011-11-18), XP028442424, DOI: 10.1016/j.ejmech.2011.11.015 *
QIAN-RU DU ET AL.: "Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents", 《BIOORGANIC & MEDICINAL CHEMISTRY》, vol. 21, 19 February 2013 (2013-02-19), XP028524316, DOI: 10.1016/j.bmc.2013.02.008 *
孙娜波等: "含吡唑环的1,3,4-噁二唑类衍生物的合成及杀菌活性研究", 《有机化学》, vol. 33, no. 1, 31 January 2013 (2013-01-31) *
张成仁等: "噁唑、苯并噁唑及1，3，4噁二唑硫醚的合成及抗肿瘤活性研究", 《有机化学》, 30 November 2007 (2007-11-30) *
雷英杰等: "超声波辐射下5-芳基-1，3，4-噁二唑-2-硫醚的合成及其抗菌活性研究", 《化学试剂》, 30 September 2013 (2013-09-30) *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104177350A (en) * 2014-07-28 2014-12-03 天津普茂科技发展有限公司 Bitriazole phenyl-substituted oxadiazole compound and preparation method and application thereof
CN107033134A (en) * 2017-05-03 2017-08-11 贵州大学 Bisamide class compound containing pyridiniujm and 1,3,4 oxadiazolyls and preparation method and application
CN107033134B (en) * 2017-05-03 2020-02-21 贵州大学 Bisamide compound containing pyridinium and 1,3, 4-oxadiazolyl and preparation method and application thereof
CN108218848A (en) * 2018-01-22 2018-06-29 贵州大学 A kind of trifluoromethyl pyridine oxadiazoles（Ether）Analog derivative and its application
CN114989155A (en) * 2021-03-01 2022-09-02 河北农业大学 1,3, 4-oxadiazole thioether derivative and preparation method and application thereof
CN114989155B (en) * 2021-03-01 2024-04-02 河北农业大学 1,3, 4-oxadiazole thioether derivative, and preparation method and application thereof

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