CN108440519A - Oxadiazole neighbour's benzene ethoxy base class compound and purposes - Google Patents
Oxadiazole neighbour's benzene ethoxy base class compound and purposes Download PDFInfo
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- CN108440519A CN108440519A CN201810285435.3A CN201810285435A CN108440519A CN 108440519 A CN108440519 A CN 108440519A CN 201810285435 A CN201810285435 A CN 201810285435A CN 108440519 A CN108440519 A CN 108440519A
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- compound
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- oxadiazole
- base class
- ethoxy base
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 18
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 230000001069 nematicidal effect Effects 0.000 claims abstract description 3
- 241000244206 Nematoda Species 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 3
- 239000003905 agrochemical Substances 0.000 claims 1
- 230000000975 bioactive effect Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000005645 nematicide Substances 0.000 abstract description 3
- 241000238631 Hexapoda Species 0.000 abstract description 2
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000005959 Fosthiazate Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- DUFVKSUJRWYZQP-UHFFFAOYSA-N fosthiazate Chemical compound CCC(C)SP(=O)(OCC)N1CCSC1=O DUFVKSUJRWYZQP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical group OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 2
- 0 CCOc1ccccc1C(N=C(*)C*)=N Chemical compound CCOc1ccccc1C(N=C(*)C*)=N 0.000 description 2
- PPCUNNLZTNMXFO-ACCUITESSA-N Imicyafos Chemical compound CCCSP(=O)(OCC)N1CCN(CC)\C1=N/C#N PPCUNNLZTNMXFO-ACCUITESSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000243786 Meloidogyne incognita Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- XSNMWAPKHUGZGQ-UHFFFAOYSA-N fluensulfone Chemical compound FC(F)=C(F)CCS(=O)(=O)C1=NC=C(Cl)S1 XSNMWAPKHUGZGQ-UHFFFAOYSA-N 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NWIJESGVOATQTP-UHFFFAOYSA-N C#N.C(C)OC1=CC=CC=C1 Chemical compound C#N.C(C)OC1=CC=CC=C1 NWIJESGVOATQTP-UHFFFAOYSA-N 0.000 description 1
- 241000244203 Caenorhabditis elegans Species 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical class Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 241000243785 Meloidogyne javanica Species 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- OYVABZRZDZPVQD-UHFFFAOYSA-N [F].C=1C=CSC=1 Chemical compound [F].C=1C=CSC=1 OYVABZRZDZPVQD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses oxadiazole neighbour's benzene ethoxy base class compounds, and structure is as shown in formula I：
Description
The invention belongs to field of pesticides in pesticide for technical field, and in particular to oxadiazole neighbour's benzene ethoxy base class
Close object and purposes.
Background technology harmful nematode can lead to crop production reduction or influence plant growth, and the harmful nematode that China is found is
There is more than 40 kinds, mainly has Rhabdictid, pratylenchus, cyst roundworm, root-knot nematode etc., countries in the world strengthened and killed recent years
The research and development of nematode agent, principal item have fosthiazate (fosthiazate) (Formula II), fluorine thiophene worm sulfone (fluensulfone)
(formula III), imicyafos (formula IV), they all have good eelworm-killing activity.But due to fosthiazate and fluensulfone
All there is thiazole ring structure, will produce the compounds such as organophosphor and organic sulfur in production process, seriously pollute environment；Due to closing
Dipropyl sulphur can be used during at imicyafos, the compounds such as phosphorus trichloride also have environment certain harm.Existing
In some technologies, the oxadiazole neighbour's benzene ethoxy base class compound (Formulas I) and its eelworm-killing activity such as Ben Faming are not disclosed.
The purpose of the present invention is to provide a kind of structure novel, efficient, safety, cost accounting Di Evil bis- for invention content
The agricultural nematicide of azoles neighbour's benzene ethoxy base class compound.
Technical scheme is as follows：
Oxadiazole neighbour's benzene ethoxy base class compound, structure are shown in formula I：
Compound of formula I can be prepared by following reaction step：
(1) compound VI is made in reflux in toluene in compound V：
(2) using potassium carbonate or sodium carbonate as acid binding agent, compound VI is with 2- cyanoiminos -1,3-thiazoles alkane in acetic acid second
It is reacted at room temperature in ester and compound I is made：
Advantages of the present invention and good effect：
Mu Qian oxadiazole insecticides commercial varieties are considerably less, the compounds of this invention in the structure simultaneously Han You oxadiazoles
It is novel one kind, wide spectrum, absorbability nematicide, the eelworm-killing activity with superelevation with thiazole cyanogen imine structure.To southern root
The insecticidal activity test result of tie lines worm shows：Compound of formula I, up to 95%, and only has 85% in 1ppm with fosthiazate under concentration；
In 0.1ppm, the compounds of this invention still has 75% suppression to kill rate, and fosthiazate only has 20% suppression to kill rate under the concentration.This
Invention compound is nitrogen cyclics, is had the characteristics that beneficial organism hypotoxicity, degradable, environmental-friendly.This compound
Production process is simple, and reaction condition is mild, does not generate by-product, and production cost is low.Meanwhile it is short to make up oxadiazole insecticides
Scarce problem has very positive meaning to the improvement of China's resistant insect.Therefore, the compounds of this invention is as pesticides discovery
New varieties have ultra high efficiency, low resistance, simple production process, low cost and advantages of environment protection, have and are killed as initiative property
The great potential of nematode agent new varieties industrialization.
Nematicidal composition the invention also includes compound of formula I as active component further includes agricultural in the composition
With acceptable carrier in forestry.
The compounds of this invention can be used alone, can also be used with other active compounds when preventing nematode evil, with
Improve the comprehensive performance of product.
The composition of the compounds of this invention can be made preparation use, the compounds of this invention be scattered in as active component or
It is dissolved in carrier or solvent, adds suitable surfactant that suspending agent, microemulsion, missible oil and aqueous emulsion etc. is made.
It should be clear that in scope defined by the claims of the present invention, various transformation and change can be carried out.
Specific implementation mode：
Example is synthesized below and raw result of surveying can be used to further illustrate the present invention, but is not intended to limit the present invention.
Synthesize example
The preparation of example 1, compound of formula I
(1) synthesis of compound VII：
Be separately added into 250mL there-necked flasks the adjacent cyanophenols of 5.95g (0.05mol), 20mL 10%NaOH aqueous solutions and
80mL toluene is heated to 70 DEG C, at this temperature insulation reaction 1h.After 1h, 60 DEG C are cooled to, 9.24g sulfuric acid two is slowly added dropwise
Ethyl ester, drop, which finishes, is warming up to 70 DEG C the reaction was continued 2h, and the adjacent cyanophenol of TLC detections disappears, and cool down liquid separation, and toluene layer is taken to rotate light
Yellow oily liquid 2- ethoxybenzene formonitrile HCN 6.98g, yield 95%.
(2) synthesis of compound VIII：
150mL ethyl alcohol, 4.14g (0.06mol) hydroxylamine hydrochlorides and 6g (0.06mol) three are added into 250mL three-necked flasks
Ethamine is heated to 50-60 DEG C of reaction 1h.7.2g compound VII are added after 1h into flask, temperature rising reflux reacts 4h, TLC detections
Compound VII disappears, and revolving removes ethyl alcohol, and 150mL water is added into flask, dissolves triethylamine hydrochloride, and residue filters, filter
Cake is compound VIII, and white solid 9.61g, yield 89% are obtained after drying.
(3) synthesis of compound IX
150mL ethyl acetate, tri- second of 9.00g (0.05mol) compound VIII and 6g are added into 250mL three-necked flasks
6.78g (0.06mol) chloracetyl chloride is slowly added dropwise under ice-water bath stirring condition for amine, after reacting 4h, TLC detection compounds VIII
It disappears.Liquid separation is washed, takes ethyl acetate layer, revolving removes after ethyl acetate to obtain dark red oil thick liquid, with methanol or different
Faint yellow solid 9.75g, yield 76% are obtained after propyl alcohol recrystallization.
(4) synthesis of compound X
12.7g (0.05mol) compound IX, 150mL toluene is added into 150mL three-necked flasks, temperature rising reflux dehydration is anti-
Answer 6h, TLC detection compounds IX disappears, and revolving obtains dark red oil thick liquid to get compound X except toluene, with methanol or
Recrystallisation from isopropanol obtains faint yellow solid 10.37g, yield 87%.
(5) synthesis of compound I
11.8g (0.05mL) compounds X, 150mLDMF, 8.28g (0.05mL) K is added into 150mL three-necked flasks2CO3
And 6.35g thiazolidines, 4h is reacted at 80 DEG C, TLC detection compounds X disappears.It filters, takes filtrate, 300mL is added after cooling
Water has a large amount of solids to be precipitated, and is filtered after stirring a period of time, filter cake is product Compound I.White solid is obtained after drying
14.15g yield 86%.
The characterization of compound of formula I：
1H-NMR (500MHz, DMSO)：δ/ppm 1.312-1.3929(t,3H),3.563-3.637(t,2H),4.094-
4.191(m,4H),5.08(s,2H),7.065-7.135(t,1H),7.188-7.245(d,1H),7.508-7.583(m,1H),
7.793-7.852(q,1H).Fusing point：175.6-179.4℃
Biological activity determination embodiment
Example 2, insecticidal activity assay
The live body active testing that Meloidogyne incognita has been carried out to the compounds of this invention, is measured using the method for tagging, will
30 nematodes are respectively put into the compound of formula I of prepared various concentration and fosthiazate liquid, after 48h is handled,
The death of nematode and the case where going down, calculate virulence, experiment is repeated 3 times, is averaged under microscope.Result is summarized in table
1。
Table 1 is to Meloidogyne incognita activity killing rate
By test result it is found that compound I has excellent eelworm-killing activity, in 10ppm, the activity of compound I is same
In fosthiazate, up to 100%；In 1ppm or less, the activity of compound I is significantly higher than fosthiazate.
Claims (3)
1. oxadiazole neighbour's benzene ethoxy base class compound, structure is as shown in formula I：
2. the purposes of oxadiazole neighbour benzene ethoxy base class compound according to claim 1, it is characterised in that I chemical combination of formula
Object is used as agricultural chemical insecticide, single use or is applied in combination with other bioactive compound, is used as prevention agricultural or forestry
Nematode does harm to.
3. a kind of nematicidal composition, being containing type I compound described in claim 1 can in active component and agricultural or forestry
The carrier of receiving.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810285435.3A CN108440519B (en) | 2018-04-03 | 2018-04-03 | Oxadiazole o-phenylethoxy compound and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810285435.3A CN108440519B (en) | 2018-04-03 | 2018-04-03 | Oxadiazole o-phenylethoxy compound and application thereof |
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| Publication Number | Publication Date |
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| CN108440519B CN108440519B (en) | 2020-10-23 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109320471A (en) * | 2018-11-08 | 2019-02-12 | 青岛科技大学 | 3- (2,6- difluorophenyl) -1,2,4- furodiazole compound and its application |
| CN109336882A (en) * | 2018-11-07 | 2019-02-15 | 青岛科技大学 | A kind of fluorine-containing pyridine acyl piperazine compounds and its application |
| CN111635397A (en) * | 2020-06-23 | 2020-09-08 | 南通大学 | Preparation and application of 3- (4-trifluoromethylphenyl) -1,2, 4-oxadiazole derivative containing five-membered nitrogen heterocycle |
| CN111675704A (en) * | 2020-06-23 | 2020-09-18 | 南通大学 | 2-substituent imidazole alkane compound containing oxadiazole heterocyclic structure and preparation method and application thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109336882A (en) * | 2018-11-07 | 2019-02-15 | 青岛科技大学 | A kind of fluorine-containing pyridine acyl piperazine compounds and its application |
| CN109336882B (en) * | 2018-11-07 | 2021-08-17 | 青岛科技大学 | Fluorine-containing pyridine acyl piperazine compound and application thereof |
| CN109320471A (en) * | 2018-11-08 | 2019-02-12 | 青岛科技大学 | 3- (2,6- difluorophenyl) -1,2,4- furodiazole compound and its application |
| CN109320471B (en) * | 2018-11-08 | 2021-09-21 | 青岛科技大学 | 3- (2, 6-difluorophenyl) -1,2, 4-oxadiazole compound and application thereof |
| CN111635397A (en) * | 2020-06-23 | 2020-09-08 | 南通大学 | Preparation and application of 3- (4-trifluoromethylphenyl) -1,2, 4-oxadiazole derivative containing five-membered nitrogen heterocycle |
| CN111675704A (en) * | 2020-06-23 | 2020-09-18 | 南通大学 | 2-substituent imidazole alkane compound containing oxadiazole heterocyclic structure and preparation method and application thereof |
| CN111635397B (en) * | 2020-06-23 | 2022-10-25 | 南通大学 | Preparation and application of 3- (4-trifluoromethylphenyl) -1,2,4-oxadiazole derivative containing five-membered nitrogen heterocycle |
| CN111675704B (en) * | 2020-06-23 | 2022-11-01 | 南通大学 | 2-substituent imidazole alkane compound containing oxadiazole heterocyclic structure and preparation method and application thereof |
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