CN113061120B - Styryl oxadiazole compound and preparation method and application thereof - Google Patents
Styryl oxadiazole compound and preparation method and application thereof Download PDFInfo
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- -1 Styryl oxadiazole compound Chemical class 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000003899 bactericide agent Substances 0.000 claims abstract description 8
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 241000123650 Botrytis cinerea Species 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 241000223602 Alternaria alternata Species 0.000 claims description 3
- 241001480061 Blumeria graminis Species 0.000 claims description 3
- 241000223195 Fusarium graminearum Species 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 241001123567 Puccinia sorghi Species 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 3
- 238000012360 testing method Methods 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000003814 drug Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000233616 Phytophthora capsici Species 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- LDPXOYHMGOQPIV-JLHYYAGUSA-N methyl (2e)-2-[2-(bromomethyl)phenyl]-2-methoxyiminoacetate Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CBr LDPXOYHMGOQPIV-JLHYYAGUSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- ZEOMRHKTIYBETG-UHFFFAOYSA-N 2-phenyl-1,3,4-oxadiazole Chemical class O1C=NN=C1C1=CC=CC=C1 ZEOMRHKTIYBETG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- PQTOEMDZBASDHQ-DUXPYHPUSA-N 5-[(e)-2-(2,4-dichlorophenyl)ethenyl]-3h-1,3,4-oxadiazole-2-thione Chemical compound ClC1=CC(Cl)=CC=C1\C=C\C1=NNC(=S)O1 PQTOEMDZBASDHQ-DUXPYHPUSA-N 0.000 description 1
- KNRDDHQQKURIEX-VOTSOKGWSA-N 5-[(e)-2-phenylethenyl]-3h-1,3,4-oxadiazole-2-thione Chemical compound O1C(=S)NN=C1\C=C\C1=CC=CC=C1 KNRDDHQQKURIEX-VOTSOKGWSA-N 0.000 description 1
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 description 1
- XFZZDIHCNHYESF-UHFFFAOYSA-N 7-amino-1-bromo-4-phenyl-5,7,8,9-tetrahydrobenzo[7]annulen-6-one Chemical compound C=12CC(=O)C(N)CCC2=C(Br)C=CC=1C1=CC=CC=C1 XFZZDIHCNHYESF-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 1
- 239000005588 Oxadiazon Substances 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241001123668 Verticillium dahliae Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention relates to styryl oxadiazole compounds shown as a structural formula I, a preparation method thereof and application of the styryl oxadiazole compounds as bactericides.
Wherein R is1～R2Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl or C3-C5 allyl; r is selected from: hydrogen, 4-bromo, 2, 4-dichloro.
Description
Technical Field
The invention relates to a preparation method and application of a new compound, in particular to a styryl oxadiazole compound and application thereof in preparing a bactericide.
Background
The pesticide is famone, herbicide oxadiazon, oxadiargyl and the like.
Ihaojiao et al [ CN104592216B, 2017.2.15 grant ] describe the preparation of 5-phenyl-1, 3, 4-oxadiazole derivatives (A). The 5-phenyl-1, 3, 4-oxadiazole derivative is used as a bactericide for killing rhizoctonia solani, sclerotinia sclerotiorum, botrytis cinerea, erysiphe graminis and phytophthora capsici.
In 2006, Li et al [ Bioorganic & Medicinal Chemistry Letters,2006,16(8): 2278-.
R＝H，4-OCH3，4-OCH2C6H5，3-Cl，2,3-Cl2，2,4-Cl2，2,5-Cl2，2,4-Cl2-5-F，2-F，4-F，2-F-4-Br，2,3-F2，4-CF3，2-I，4-NO2
Wherein compound B (R ═ 4-F, 2-F-4-Br, 2,3-F250mg/L) of the inhibitor, the inhibition rates of the verticillium dahliae and the botrytis cinerea are both 100 percent.
The invention aims to develop a styryl oxadiazole compound bactericide with a novel structure.
Disclosure of Invention
The invention aims to provide styryl oxadiazole compounds, a preparation method thereof and application of the styryl oxadiazole compounds as bactericides.
In order to solve the technical problem, the invention provides the following technical scheme:
the first aspect of the technical scheme of the invention provides a styryl oxadiazole compound shown as a structural formula I:
wherein R is1～R2Selected from: C1-C2 alkyl, C3-C4 straight-chain alkyl or C3-C5 allyl; r is selected from: hydrogen, 4-bromo, 2, 4-dichloro.
In a second aspect of the technical scheme of the present invention, a preparation method of styryl oxadiazole compounds is provided, wherein the preparation reaction of the compound represented by formula I is as follows:
wherein R is1～R2Selected from the group consisting of: C1-C2 alkyl, C3-C4 straight-chain alkyl or C3-C5 allyl; r is selected from: hydrogen, 4-bromo, 2, 4-dichloro; x is selected from: chlorine, bromine or iodine.
The third aspect of the technical scheme of the invention is to provide an application of the styryl oxadiazole compound in the preparation of bactericides.
The beneficial technical effects are as follows:
the styryl oxadiazole compound is a compound with bactericidal activity or insecticidal activity.
Detailed Description
The following examples are intended to illustrate the invention without further limiting it.
Example 1
(E) Preparation of methyl (E) -2- (methoxyimino) -2- (2- (((5- ((E) -styryl) -1,3, 4-oxadiazol-2-yl) mercapto) methyl) phenyl) acetate (I1)
1.0mmol of (E) -5-styryl-2-mercapto-1, 3, 4-oxadiazole, 1.1mmol of potassium carbonate, 5mL of acetonitrile and 0.6mmol of potassium iodide, adding 1.05mmol of (E) -2-bromomethyl-alpha-methoxyimino phenylacetic acid methyl ester in batches under stirring at room temperature, heating to reflux, reacting for 3h, desolventizing under reduced pressure, extracting with ethyl acetate, washing with water, drying with anhydrous sodium sulfate, desolventizing, and separating by column chromatography (V)Petroleum ether∶VEthyl acetate10: 1) to give methyl (E) -2- (methoxyimino) -2- (2- (((5- ((E) -styryl) -1,3, 4-oxadiazol-2-yl) mercapto) methyl) phenyl) acetate (I1) in 83.8% yield; white solid with a melting point of 140-142 ℃;1H NMR(400MHz，CDCl3)δ：7.55～6.94(m，9H，Ar-H)，7.62(d，J＝6.8Hz，1H，CH＝CH)，7.18(d，J＝6.8Hz，1H，CH＝CH)，4.39(s，2H，SCH2)，4.09(s，3H，NOCH3)，3.90(s，3H，OCH3)；13C NMR(101MHz，CDCl3)δ：165.46，163.50，163.24，149.05，138.70，134.72，133.99，130.57，130.22，129.94，129.86，129.00，128.66，128.09，127.46，109.58，63.93，53.16，34.72。
example 2
(E) Preparation of methyl (E) -2- (2- (((5- ((E) -4-bromophenylvinyl) -1,3, 4-oxadiazol-2-yl) mercapto) methyl) phenyl) -2- (methoxyimino)) acetate (I19)
Prepared according to the method of example 1, 1.0mmol of (E) -5- (4-bromostyreneReaction of yl) -2-mercapto-1, 3, 4-oxadiazole and 1.05mmol of (E) -2-bromomethyl- α -methoxyiminophenylacetic acid methyl ester for 3h to give (E) -methyl 2- (2- (((5- ((E) -4-bromostyryl) -1,3, 4-oxadiazol-2-yl) mercapto) methyl) phenyl) -2- (methoxyimino)) acetate (I19) in 78.9% yield;1H NMR(400MHz，CDCl3)δ：7.65～7.35(m，8H，2×C6H4)，7.18(d，J＝16.4Hz，1H，CH＝CH)，6.97(d，J＝16.4Hz，1H，CH＝CH)，4.39(s，2H，CH2)，4.08(s，3H，NOCH3)，3.90(s，3H，OCH3)。
example 3
(E) Preparation of methyl (l) -2- (2- (((5- ((E) -2, 4-dichlorostyryl) -1,3, 4-oxadiazol-2-yl) mercapto) methyl) phenyl) -2- (methoxyimino)) acetate (I3)
Prepared according to the method of example 1, 1.0mmol of (E) -5- (2, 4-dichlorostyryl) -2-mercapto-1, 3, 4-oxadiazole and 1.05mmol of (E) -2-bromomethyl- α -methoxyiminophenylacetic acid methyl ester were reacted for 3h to give (E) -methyl 2- (2- (((5- ((E) -2, 4-dichlorostyryl) -1,3, 4-oxadiazol-2-yl) mercapto) methyl) phenyl) -2- (methoxyimino)) acetate (I3) in 74.5% yield; yellow solid with melting point of 129-131 ℃;1H NMR(400MHz，CDCl3)δ：7.74(d，J＝16.4Hz，1H，CH＝CH)，7.65～7.15(m，4H，C6H4)，7.44(m，3H，C6H3)，6.97(d，J＝16.4Hz，1H，CH＝CH)，4.40(s，2H，SCH2)，4.09(s，3H，NOCH3)，3.90(s，3H，OCH3)；13C NMR(101MHz，CDCl3)δ：164.97，164.15，163.24，149.06，136.03，134.99，133.91，133.16，131.52，130.59，130.24，130.03，129.87，128.70，128.15，127.73，112.44，63.95，53.19，34.74。
example 4
Determination of bactericidal activity of styryl oxadiazole compound
Purpose of the test
The toxicity of the new compound to various pathogenic bacteria under the test concentration is measured indoors, and the bactericidal activity of the new compound is preliminarily evaluated.
2 conditions of the test
2.1 test target
Cucumber Botrytis cinerea (Botrytis cinerea), Alternaria tabaci (Alternaria alternata), wheat gibberellic disease (Gibberella zeae), Sclerotinia sclerotiorum (Sclerotinia sclerotiorum) and Phytophthora capsici (Phytophthora capsicii), all of which are stored in a refrigerator (4-8 ℃), inoculated into a culture dish from a test tube slant for 2-3 days before the test, and cultured at a proper temperature for the test. The culture medium for experiments is potato agar medium (PDA).
2.2 culture conditions
The culture conditions of the test target and the tested target are that the temperature is 25 +/-5 ℃ and the relative humidity is 65 +/-5 percent
2.3 instrumentation
A beaker, a pipette, a measuring cylinder, a culture dish, an autoclave, a constant temperature biochemical incubator and the like.
Design of the experiment
3.1 test agents: the compounds of the examples.
3.2 test concentrations
The concentration of the in vitro medicament is set to be 25 mg/L; the concentration of the corn rust disease germ and wheat powdery mildew disease medicament is set to be 500 mg/L.
3.3 preparation of the medicament
Raw materials: weighing the required amount by using a ten-thousandth electronic balance; solvent: n, N-Dimethylformamide (DMF), 0.2%; emulsifier: tween80, 0.1%;
and (3) ordinary sieve determination: accurately weighing 0.0500g of sample, dissolving with 0.20mL of DMMF, adding 98.8mL of sterile water containing 0.1% of Tween80 emulsifier, stirring uniformly, and preparing into 500mg/L concentration solution for later use.
4 test method
Refer to "evaluation of biological Activity of pesticides SOP".
Botrytis cinerea, alternaria alternata, fusarium graminearum, sclerotinia sclerotiorum and phytophthora capsici: according to the raw measurement standard method NY/T1156.2-2006, a drug-containing culture medium method is adopted: 2mL of each 500mg/L compound solution was added to 38mL of PDA cooled to 45 ℃ to prepare a drug-containing medium plate with a final concentration of 25 mg/L. Then, 6.5mm diameter hypha blocks are taken from the edge of the cultured test germ colony and transferred to a culture medium containing the medicine, and the treatment is repeated for 4 times. After the treatment, the cells were cultured in a constant temperature biochemical incubator at 28 ℃ for 4 days, and the diameter of the colonies was measured to calculate the growth inhibition rate.
5 evaluation of Fungicide Activity
After treatment, the morbidity and the hypha growth of the leaves and the plants are regularly observed and recorded, and the control effect and the inhibition rate are calculated according to the disease index and the hypha diameter.
The in vitro bactericidal activity (25. mu.g/mL) and in vivo bactericidal activity (500mg/L) of styryl oxadiazole compounds are shown in Table 1 below:
TABLE 1 fungicidal Activity of Compounds I1-I3 (25. mu.g/mL)
The bactericidal activity (control effect) of the compound I3(500mg/L) on the living bodies of erysiphe graminis and corn rust is 50% and 95% respectively.
The activity results show that: the styryl oxadiazole compound has good bactericidal activity and can be used for preparing bactericides and applied to agriculture.
Claims (3)
1. A styryl oxadiazole compound shown as a structural formula I:
wherein R is1～R2Selected from: C1-C2 alkyl or C3-C4 straightA chain alkyl group; r is selected from: hydrogen, 4-bromo, 2, 4-dichloro.
2. The process for producing a styryl oxadiazole compound according to claim 1, characterized by the following reaction:
wherein, R, R1And R2Is as defined in claim 1; x is selected from: chlorine, bromine or iodine.
3. Use of the styryl oxadiazole compound of claim 1 for preparing a bactericide against Alternaria alternata, Fusarium graminearum, Botrytis cinerea, Blumeria graminis, or Puccinia zeae.
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| BR0007822A (en) * | 1999-01-15 | 2002-02-19 | Bayer Ag | Derivatives of n-alkoxy-phenylcarbamates |
| MXPA03002442A (en) * | 2000-09-19 | 2004-05-05 | Dow Agrosciences Llc | Thiazole derivatives of 2-methoxyimino-2-(pyridinyloxymethyl)-phenyl-acetamides useful as fungicides. |
| CN102603669B (en) * | 2012-04-05 | 2014-10-22 | 南开大学 | Derivatives of alpha-methoxyl imino-5-methyl-1,2,3-thiadiazole-4- carboxylic acid methyl ester and preparation methods and uses thereof |
| CN103980223B (en) * | 2014-05-23 | 2016-11-09 | 贵州大学 | 2-substituent group-5-substituted anilinic-1,3,4-diazoles derivant and synthetic method thereof and application |
| CN109535144A (en) * | 2019-01-08 | 2019-03-29 | 贵州大学 | A kind of 1,3,4- oxadiazoles thio-ether type compounds and its preparation method and application |
| CN109651350B (en) * | 2019-01-11 | 2022-05-24 | 贵州大学 | Heterocyclic substituted 1,3,4-oxa (thia) diazoles compound and preparation method and application thereof |
| CN110367265B (en) * | 2019-08-26 | 2022-02-15 | 浙江工业大学 | Application of stilbene analogue containing phenylthiazole structure as bactericide |
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2021
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