CN103626737A - 一种含吡啶的三唑类化合物作为杀菌剂的应用 - Google Patents
一种含吡啶的三唑类化合物作为杀菌剂的应用 Download PDFInfo
- Publication number
- CN103626737A CN103626737A CN201310663929.8A CN201310663929A CN103626737A CN 103626737 A CN103626737 A CN 103626737A CN 201310663929 A CN201310663929 A CN 201310663929A CN 103626737 A CN103626737 A CN 103626737A
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- Prior art keywords
- phenyl
- compound
- formula
- pyridine
- arh
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 45
- -1 triazole compound Chemical class 0.000 title claims abstract description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 4
- 239000003899 bactericide agent Substances 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 240000008067 Cucumis sativus Species 0.000 claims abstract description 10
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims abstract description 10
- 235000007688 Lycopersicon esculentum Nutrition 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 241000223218 Fusarium Species 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003852 triazoles Chemical class 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 241000293040 Xanthomonas gardneri Species 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical group ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 2
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 241000227653 Lycopersicon Species 0.000 claims 1
- 239000012065 filter cake Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 240000003768 Solanum lycopersicum Species 0.000 abstract description 8
- 241000123650 Botrytis cinerea Species 0.000 abstract 1
- 101100117236 Drosophila melanogaster speck gene Proteins 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 7
- 238000011081 inoculation Methods 0.000 description 7
- 229940073608 benzyl chloride Drugs 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000136 polysorbate Polymers 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 description 1
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005760 Difenoconazole Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LXMQMMSGERCRSU-UHFFFAOYSA-N Fluotrimazole Chemical compound FC(F)(F)C1=CC=CC(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)N2N=CN=C2)=C1 LXMQMMSGERCRSU-UHFFFAOYSA-N 0.000 description 1
- 239000005787 Flutriafol Substances 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003020 moisturizing effect Effects 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
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
化合物 | 番茄细菌性斑点病 | 黄瓜枯萎病 | 番茄灰霉病 |
1 | 53.57 | 66.67 | 24.44 |
2 | 5.21 | 64.86 | 20.42 |
3 | 50.30 | 65.56 | 28.89 |
4 | 43.15 | 64.44 | 24.44 |
5 | 46.23 | 66.94 | 14.44 |
6 | 71.43 | 63.93 | 20.00 |
7 | 73.51 | 63.33 | 16.67 |
8 | 62.20 | 66.67 | 15.56 |
9 | 66.98 | 64.44 | 17.78 |
10 | 65.67 | 48.89 | 13.33 |
11 | 67.86 | 53.33 | 22.22 |
12 | 75.00 | 53.33 | 15.56 |
13 | 79.76 | 55.56 | 12.22 |
14 | 75.89 | 48.89 | 20.00 |
Claims (5)
Priority Applications (1)
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CN201310663929.8A CN103626737B (zh) | 2013-12-10 | 2013-12-10 | 一种含吡啶的三唑类化合物作为杀菌剂的应用 |
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CN201310663929.8A CN103626737B (zh) | 2013-12-10 | 2013-12-10 | 一种含吡啶的三唑类化合物作为杀菌剂的应用 |
Publications (2)
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CN103626737A true CN103626737A (zh) | 2014-03-12 |
CN103626737B CN103626737B (zh) | 2015-10-28 |
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Country Status (1)
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CN (1) | CN103626737B (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105017247A (zh) * | 2015-06-16 | 2015-11-04 | 浙江工业大学 | 一种[1,2,4]三唑[4,3-α]吡啶-3(2H)-硫酮衍生物的制备方法 |
CN105017248A (zh) * | 2015-06-16 | 2015-11-04 | 浙江工业大学 | 一种[1,2,4]三唑[4,3-α]吡啶-3(2H)-硫酮类化合物的制备方法及其应用 |
CN106135228A (zh) * | 2016-07-28 | 2016-11-23 | 浙江工业大学 | 一种含甲基吡唑的三唑类化合物在制备杀菌剂中的应用 |
CN106220610A (zh) * | 2016-07-28 | 2016-12-14 | 浙江工业大学 | 一种含甲基吡唑的三唑类化合物及其制备方法和应用 |
EP3210469A1 (de) | 2016-02-23 | 2017-08-30 | Bayer Cropscience AG | Verwendung von substituierten thio-1,2,4-triazolen zur steigerung der stresstoleranz in pflanzen |
Citations (2)
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CN102850341A (zh) * | 2012-09-05 | 2013-01-02 | 浙江工业大学 | 一种噻二唑类化合物及其制备与应用 |
CN103183662A (zh) * | 2011-12-30 | 2013-07-03 | 江苏天晟药业有限公司 | 一类含吡啶环的三氮唑衍生物及其制法 |
-
2013
- 2013-12-10 CN CN201310663929.8A patent/CN103626737B/zh not_active Expired - Fee Related
Patent Citations (2)
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CN103183662A (zh) * | 2011-12-30 | 2013-07-03 | 江苏天晟药业有限公司 | 一类含吡啶环的三氮唑衍生物及其制法 |
CN102850341A (zh) * | 2012-09-05 | 2013-01-02 | 浙江工业大学 | 一种噻二唑类化合物及其制备与应用 |
Non-Patent Citations (6)
Title |
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HACER BAYRAK ET AL.: "Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》, vol. 44, 26 June 2008 (2008-06-26), pages 1057 - 1066, XP025989456, DOI: doi:10.1016/j.ejmech.2008.06.019 * |
SEYED ADEL MOALLEM ET AL.: "Synthesis and Evaluation of Pyridinyltriazoles as Inhibitors of p38 MAP Kinase", 《IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES》, vol. 15, no. 4, 31 August 2012 (2012-08-31), pages 945 - 950 * |
STN: "REGISTRY", 《STN COLUMBUS》, 15 March 2004 (2004-03-15), pages 1 - 3 * |
YAN-BIN ZHANG ET AL.: "Synthesis, molecular modeling,and biological evaluation of 1,2,4-triazole derivatives containing pyridine as potential anti-tumor agents", 《MED CHEM RES》, vol. 22, 15 November 2012 (2012-11-15), pages 3193 - 3203 * |
晁淑军等: "含均三唑环的新型联苯四唑衍生物的合成及抗菌活性", 《化学学报》, vol. 63, no. 6, 31 December 2005 (2005-12-31), pages 525 - 532 * |
童建颖等: "含邻氟苯基的1,2,4-三唑类衍生物的合成及杀菌活性研究", 《有机化学》, vol. 32, 15 August 2012 (2012-08-15), pages 2373 - 2377 * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105017247A (zh) * | 2015-06-16 | 2015-11-04 | 浙江工业大学 | 一种[1,2,4]三唑[4,3-α]吡啶-3(2H)-硫酮衍生物的制备方法 |
CN105017248A (zh) * | 2015-06-16 | 2015-11-04 | 浙江工业大学 | 一种[1,2,4]三唑[4,3-α]吡啶-3(2H)-硫酮类化合物的制备方法及其应用 |
EP3210469A1 (de) | 2016-02-23 | 2017-08-30 | Bayer Cropscience AG | Verwendung von substituierten thio-1,2,4-triazolen zur steigerung der stresstoleranz in pflanzen |
CN106135228A (zh) * | 2016-07-28 | 2016-11-23 | 浙江工业大学 | 一种含甲基吡唑的三唑类化合物在制备杀菌剂中的应用 |
CN106220610A (zh) * | 2016-07-28 | 2016-12-14 | 浙江工业大学 | 一种含甲基吡唑的三唑类化合物及其制备方法和应用 |
CN106135228B (zh) * | 2016-07-28 | 2018-11-13 | 浙江工业大学 | 一种含甲基吡唑的三唑类化合物在制备杀菌剂中的应用 |
CN106220610B (zh) * | 2016-07-28 | 2019-03-05 | 浙江工业大学 | 一种含甲基吡唑的三唑类化合物及其制备方法和应用 |
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