CN108477170A - A kind of quinolines and preparation method thereof and the purposes in controlling plant diseases - Google Patents
A kind of quinolines and preparation method thereof and the purposes in controlling plant diseases Download PDFInfo
- Publication number
- CN108477170A CN108477170A CN201810291712.1A CN201810291712A CN108477170A CN 108477170 A CN108477170 A CN 108477170A CN 201810291712 A CN201810291712 A CN 201810291712A CN 108477170 A CN108477170 A CN 108477170A
- Authority
- CN
- China
- Prior art keywords
- quinolines
- chloride
- 400mhz
- esi
- chloroform
- 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
- 201000010099 disease Diseases 0.000 title claims abstract description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 20
- 150000003248 quinolines Chemical class 0.000 title claims abstract description 13
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 241000221785 Erysiphales Species 0.000 claims abstract description 15
- 241000223218 Fusarium Species 0.000 claims abstract description 14
- 241000196324 Embryophyta Species 0.000 claims abstract description 12
- 241000221696 Sclerotinia sclerotiorum Species 0.000 claims abstract description 12
- 241000813090 Rhizoctonia solani Species 0.000 claims abstract description 11
- 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 10
- 241001330975 Magnaporthe oryzae Species 0.000 claims abstract description 10
- 240000001980 Cucurbita pepo Species 0.000 claims abstract description 9
- 235000000832 Ayote Nutrition 0.000 claims abstract description 7
- 235000009854 Cucurbita moschata Nutrition 0.000 claims abstract description 7
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 claims abstract description 7
- 235000015136 pumpkin Nutrition 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000000843 powder Substances 0.000 claims abstract description 4
- 244000052616 bacterial pathogen Species 0.000 claims description 2
- 244000052769 pathogen Species 0.000 claims description 2
- 244000241257 Cucumis melo Species 0.000 claims 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 240000008067 Cucumis sativus Species 0.000 abstract description 13
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 10
- 238000012360 testing method Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000000855 fungicidal effect Effects 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract description 2
- 238000002474 experimental method Methods 0.000 description 33
- 239000007787 solid Substances 0.000 description 28
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 21
- 241000894006 Bacteria Species 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- 239000005822 Propiconazole Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 239000000575 pesticide Substances 0.000 description 8
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 8
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 7
- 241000157855 Cinchona Species 0.000 description 6
- 235000001258 Cinchona calisaya Nutrition 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 6
- 229960000948 quinine Drugs 0.000 description 6
- 241000223195 Fusarium graminearum Species 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 150000003851 azoles Chemical class 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000005760 Difenoconazole Substances 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 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 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical class C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 235000009852 Cucurbita pepo Nutrition 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 239000005811 Myclobutanil Substances 0.000 description 2
- 241000317981 Podosphaera fuliginea Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229960001076 chlorpromazine Drugs 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- 201000004792 malaria Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-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
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- -1 2- bromo propionyl chloros Chemical compound 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- MQZNDDUMJVSIMH-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropanoyl chloride Chemical compound ClCC(C)(C)C(Cl)=O MQZNDDUMJVSIMH-UHFFFAOYSA-N 0.000 description 1
- 241000288027 Chrysolophus pictus Species 0.000 description 1
- 241001660788 Cinchona calisaya Species 0.000 description 1
- 235000021515 Cinchona ledgeriana Nutrition 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000015220 Febrile disease Diseases 0.000 description 1
- 241000879806 Fusarium oxysporum f. sp. vasinfectum Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241001582888 Lobus Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VTVABQISWDLHRQ-UHFFFAOYSA-N O=C(C1CC1)Oc1cc(C(F)(F)F)nc2c1cccc2C(F)(F)F Chemical compound O=C(C1CC1)Oc1cc(C(F)(F)F)nc2c1cccc2C(F)(F)F VTVABQISWDLHRQ-UHFFFAOYSA-N 0.000 description 1
- KDFWZVGEWQMCAZ-UHFFFAOYSA-N O=C(Oc1ccccc1)Oc1cc(C(F)(F)F)nc2c1cccc2C(F)(F)F Chemical compound O=C(Oc1ccccc1)Oc1cc(C(F)(F)F)nc2c1cccc2C(F)(F)F KDFWZVGEWQMCAZ-UHFFFAOYSA-N 0.000 description 1
- 241000123069 Ocyurus chrysurus Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000016127 added sugars Nutrition 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229960001962 mefloquine Drugs 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- 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
- A01N43/42—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 condensed with carbocyclic rings
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (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)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Purposes the invention discloses a kind of quinolines and preparation method thereof and in controlling plant diseases.Test result shows:Such compound has excellent control effect to plant disease caused by cotton-wilt fusarium, gibberella saubinetii, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn and Pyricularia oryzae and to Pumpkin powdery mildew and cucumber white powder.Preparation process of the present invention is simple, raw material is cheap and easy to get, and product purity is high, and it is new fungicide to be expected to exploitation.
Description
Technical field
The invention belongs to field of natural medicinal chemistry and technical field of pesticide, disclose the new use of one kind of quinoline
On the way, and in particular to quinoline is in prevention by cotton-wilt fusarium (Fusarium oxysporum f.sp.vasinfectum
(Atk.) Snyder&Hansen), gibberella saubinetii (Fusarium graminearum), Sclerotinia sclerotiorum (Sclerotinia
Sclerotiorum), Rhizoctonia solani Kuhn (Rhizoctonia solani) and Pyricularia oryzae (Magnaporthe oryzae) draw
The plant disease risen and the field control effect to Pumpkin powdery mildew and cucumber white powder.
Background technology
Currently, being mainly controlled by chemical pesticides by fungus-caused plant disease, although many commercialization fungicide at present
Control effect is preferable, but being widely used due to these chemical pesticides, and leading to " 3R ", (residue residuals, resistance are anti-
Property, resurgence it is rampant once again) problem is on the rise, caused the very big concern of society.Therefore, research and development are efficient
Safety pesticide comes the important topic that the prevention and control plant disease person that has become plant protection work faces and sustainable development of agricultural production
Only way, and a part of the botanical pesticide as biogenic pesticide, because generally acknowledge its have low toxicity, noresidue, high selectivity,
The advantages that easily decomposition, pest are not likely to produce drug resistance, and receive researcher's favor.Therefore, it finds and screens from plant resources
Potential sterilization secondary metabolite, and becoming new type bactericide initiative using it as guide structure progress Optimal Structure Designing
One of important channel.
Quinine is very famous alkaloids natural drug, is commonly called as quinine, is from madder wort golden pheasant earliest
Extraction obtains in Na Shu (Cinchona ledgeriana (Howard) Moens ex Trim) and its bark of congener.
Quinine is to treat the specific drug of malaria, and the life of countless malaria patients has once been saved in its discovery and application.Seminar early period
It was found that quinine to Sclerotinia sclerotiorum at 50ppm, be 69.58% to the inhibitory activity of germ, we are further to similitude
Molecule Mefloquine (antimalarial) has done carry out active testing evaluation, it is found that its antibacterial activity is obviously improved.According to its activity
The selection result, we carry out derivative synthesis at its 4, have synthesized a series of new quinolines using it as parent nucleus guide structure
Object is closed, its bactericidal activity is made to have significantly more raising, also more simple in its synthetic method, economical, synthesis cost is aobvious
Writing reduces.Although the research report about quinine is more, text is had not yet to see to its application in terms of inhibiting agriculture germ
Offer report.
The present invention is using quinine as clue, and by its structure optimization and derivative synthesis, design has synthesized a series of recruits, and
It was found that target compound has preferably cotton-wilt fusarium, gibberella saubinetii, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn and Pyricularia oryzae
Fungistatic effect find that it has preferable control effect to Pumpkin powdery mildew and cucumber white powder by field trial, can be used as
A kind of novel wide-spectrum bactericide.
Invention content
The present invention provides following technical methods:One kind is for cotton-wilt fusarium, fusarium graminearum, sclerotinia sclerotiorum
The drug of bacterium, Rhizoctonia solani Kuhn and Pyricularia oryzae, wherein any compound institute in KL-1~KL-26 containing therapeutically effective amount
The quinoline (figure -2) shown.
Quinoline synthetic method of the present invention is shown in embodiment, is detached through conventional methods such as multiple silica gel column chromatographies
Sterling is obtained, through the spectroscopic techniques such as mass spectrum and nuclear magnetic resonance, it is determined that right wants quinolines KL-1~KL-26, knot
Structure formula is as shown in Figure 2.Show that quinoline of the present invention is red to cotton-wilt fusarium, wheat through active ingredients result
Mildew bacterium, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn and Pyricularia oryzae show stronger inhibiting effect, can be used for preparing sterilization
Agent.
Description of the drawings
Fig. 1 compounds are found and optimization process
Fig. 2 quinoline derivatives
Specific implementation mode
Embodiment 1
The synthesis of quinoline (KL-1)
Method one:
Method two:
Its specific synthetic operation is as follows:
Method one:By raw material 2,0.247 gram of bis- Trifluoromethylquinocarboxylics of 8- are added in 50mL single port bottles, molten with 20mL acetone
Equimolar potassium carbonate is first added in solution, and equimolar benzyl chloroformate is then added, is heated to reflux 3 hours, filters to get filtrate, boil off
Solvent purifies solvent (ethyl acetate with column chromatography:Petroleum ether=1:5) white solid is obtained.
Method two:By raw material 2,0.247 gram of bis- Trifluoromethylquinocarboxylics of 8- are added in 50mL single port bottles, and 5mL acetic acid is added
Acid anhydride is heated to reflux 3h, and plate layer chromatography tracking reaction is completed, and extra acetic anhydride is boiled off under decompression, (solvent is detached with plate layer chromatography:
Ethyl acetate:Petroleum ether=1:5) white solid is obtained.
KL-1:White solid, yield 85%;1H NMR (400MHz, Chloroform-d) δ 8.23 (dd, J=17.4,
7.9Hz, 2H), 7.80 (s, 1H), 7.75 (t, J=7.9Hz, 1H), 2.17 (s, 3H) .ESI-MS m/z:346.06[M+Na]+.
Embodiment 2
The synthesis of KL-2:Experimental procedure is changed to propionyl chloride with embodiment 1, by chloroacetic chloride.
KL-2 white solids, yield 83%;1H NMR (400MHz, Chloroform-d) δ 8.15 (dd, J=14.6,
7.9Hz, 2H), 7.74 (s, 1H), 7.67 (s, 1H), 2.77 (d, J=7.5Hz, 2H), 1.32 (t, J=7.6Hz, 3H) .ESI-
MS m/z:360.08[M+Na]+.
Embodiment 3
The synthesis of KL-3:Experimental procedure is changed to chloracetyl chloride with embodiment 1, by chloroacetic chloride.
KL-3 white solids, yield 72%;1H NMR (400MHz, Chloroform-d) δ 8.19 (dd, J=20.8,
7.9Hz, 2H), 7.79 (s, 1H), 7.72 (t, J=7.9Hz, 1H), 4.43 (s, 2H) .ESI-MS m/z:380.02[M+Na]+.
Embodiment 4
The synthesis of KL-4:Experimental procedure is changed to n-butyryl chloride with embodiment 1, by chloroacetic chloride.
KL-4 white solids, yield 84%;1H NMR(400MHz,Chloroform-d)δ8.16(s,2H),7.73(s,
1H), 7.68 (s, 1H), 2.71 (t, J=7.4Hz, 2H), 1.90-1.75 (m, 2H), 1.06 (t, J=7.4Hz, 3H) .ESI-MS
m/z:374.09[M+Na]+.
Embodiment 5
The synthesis of KL-5:Experimental procedure is changed to n-amyl chloride with embodiment 1, by chloroacetic chloride.
KL-5:White solid, yield 88%;1H NMR(400MHz,Chloroform-d)δ8.20–8.10(m,2H),
7.72 (s, 1H), 7.68 (s, 1H), 2.73 (t, J=7.5Hz, 2H), 1.79 (t, J=7.5Hz, 2H), 1.48-1.40 (m,
2H), 0.96 (t, J=7.3Hz, 3H) .ESI-MS m/z:388.11[M+Na]+.
Embodiment 6
The synthesis of KL-6:Experimental procedure is changed to isoveryl chloride with embodiment 1, by chloroacetic chloride.
KL-6 white solids, yield 89%;1H NMR (400MHz, Chloroform-d) δ 8.15 (dd, J=14.8,
7.9Hz, 2H), 7.72 (s, 1H), 7.67 (t, J=7.9Hz, 1H), 2.60 (d, J=7.1Hz, 2H), 2.34-2.22 (m, 1H),
1.07 (d, J=6.6Hz, 6H) .ESI-MS m/z:388.11[M+Na]+.
Embodiment 7
The synthesis of KL-7:Experimental procedure is changed to positive caproyl chloride with embodiment 1, by chloroacetic chloride.
KL-7 white solids, yield 86%;1H NMR (400MHz, Chloroform-d) δ 8.15 (dd, J=13.0,
7.9Hz, 2H), 7.73 (s, 1H), 7.67 (t, J=7.9Hz, 1H), 2.72 (t, J=7.5Hz, 2H), 1.80 (p, J=7.4Hz,
2H), 1.47-1.29 (m, 4H), 0.90 (t, J=6.9Hz, 3H) .ESI-MS m/z:402.13[M+Na]+..
Embodiment 8:
The synthesis of KL-8:Experimental procedure is changed to chlorobenzoyl chloride with embodiment 1, by chloroacetic chloride.
KL-8 white solids, yield 84%;1H NMR (400MHz, Chloroform-d) δ 8.24 (d, J=7.5Hz,
2H), 8.14 (d, J=7.3Hz, 1H), 8.12-8.00 (m, 1H), 7.83 (s, 1H), 7.68 (td, J=7.8,4.7Hz, 2H),
7.54 (t, J=7.7Hz, 2H) .ESI-MS m/z:408.09[M+Na]+..
Embodiment 9
The synthesis of KL-9:Experimental procedure is changed to phenyl chloroformate with embodiment 1, by chloroacetic chloride.
KL-9 white solids, yield 80%;1H NMR (400MHz, Chloroform-d) δ 8.40 (d, J=8.5Hz,
1H), 8.18 (d, J=7.3Hz, 1H), 8.00 (s, 1H), 7.75 (t, J=7.9Hz, 1H), 7.46-7.38 (m, 2H), 7.38-
7.32(m,1H),7.30–7.27(m,2H).ESI-MS m/z:441.57[M+K]+.
Embodiment 10
The synthesis of KL-10:Experimental procedure is changed to benzyl chloroformate with embodiment 1, by chloroacetic chloride.
KL-10 white solids, yield 88%;1H NMR (400MHz, Chloroform-d) δ 8.26 (dd, J=8.4,
1.4Hz, 1H), 8.13 (d, J=7.2Hz, 1H), 7.89 (s, 1H), 7.67 (t, J=7.9Hz, 1H), 7.42 (dq, J=4.5,
2.5Hz,2H),7.40–7.35(m,3H),5.32(s,2H).ESI-MS m/z:438.08[M+Na]+..
Embodiment 11
The synthesis of KL-11:Experimental procedure is changed to mesyl chloride with embodiment 1, by chloroacetic chloride.
KL-11 white solids, yield 74%;1H NMR (400MHz, Chloroform-d) δ 8.33 (d, J=8.5Hz,
1H), 8.19 (d, J=7.3Hz, 1H), 7.80 (s, 1H), 7.76 (s, 1H), 3.36 (s, 3H) .ESI-MS m/z:360.06[M+
H]+.
Embodiment 12
The synthesis of KL-12:Experimental procedure is changed to tosylate chloride with embodiment 1, by chloroacetic chloride.
KL-12 white solids, yield 79%;1H NMR(400MHz,Chloroform-d)δ8.14–8.07(m,2H),
7.93-7.87 (m, 2H), 7.69 (td, J=7.4,1.4Hz, 1H), 7.62 (t, J=7.9Hz, 1H), 7.57-7.50 (m, 3H)
.ESI-MSm/z:444.06[M+Na]+..
Embodiment 13
The synthesis of KL-13:Experimental procedure is changed to tert-butyl chloro-silicane with embodiment 1, by chloroacetic chloride.
KL-13 white solids, yield 50%;1H NMR (400MHz, Chloroform-d) δ 8.13 (d, J=7.3Hz,
1H), 8.04 (d, J=7.6Hz, 1H), 7.54 (t, J=7.9Hz, 1H), 6.77-6.69 (m, 1H), 1.10 (s, 9H), 0.40
(s,2H).ESI-MS m/z:418.13[M+Na]+.
Embodiment 14
KL-14 is synthesized:Experimental procedure is changed to 1- chlorpromazine chlorides with embodiment 1, by chloroacetic chloride.
KL-14 white solids, yield 82%;1H NMR (400MHz, Chloroform-d) δ 8.21 (d, J=8.6Hz,
1H), 8.15 (d, J=7.3Hz, 1H), 7.76-7.67 (m, 2H), 3.91 (t, J=6.3Hz, 2H), 3.22 (t, J=6.3Hz,
2H).
ESI-MS m/z:409.98[M+K]+.
Embodiment 15
KL-15 is synthesized:Experimental procedure is changed to 2- chlorpromazine chlorides with embodiment 1, by chloroacetic chloride.
KL-15 white solids, yield 34%;1H NMR (400MHz, Chloroform-d) δ 8.52 (d, J=8.5Hz,
1H), 8.14 (d, J=7.3Hz, 1H), 7.65 (t, J=7.8Hz, 1H), 7.31 (s, 1H), 4.12 (s, 1H), 1.58 (s, 3H)
.ESI-MSm/z:494.00[M+Na]+.
Embodiment 16
KL-16 is synthesized:Experimental procedure is changed to 1- chlorine n-butyryl chlorides with embodiment 1, by chloroacetic chloride.
KL-16 white solids, yield 68%;1H NMR(400MHz,Chloroform-d)δ8.28–8.18(m,2H),
7.81 (s, 1H), 7.76 (s, 1H), 3.74 (t, J=6.1Hz, 2H), 3.04 (t, J=7.2Hz, 2H), 2.43-2.24 (m,
2H).ESI-MSm/z:408.02[M+Na]+.
Embodiment 17
KL-17 is synthesized:Experimental procedure is changed to 1- chlorine n-amyl chlorides with embodiment 1, by chloroacetic chloride.
KL-17 white solids, yield 70%;1H NMR(400MHz,Chloroform-d)δ8.26–8.18(m,2H),
7.80 (s, 1H), 7.75 (t, J=7.9Hz, 1H), 3.65 (t, J=6.0Hz, 2H), 2.86 (t, J=7.1Hz, 2H), 2.16-
1.86(m,4H).ESI-MS m/z:422.07[M+Na]+.
Embodiment 18
KL-18 is synthesized:Experimental procedure is changed to isobutyryl chloride with embodiment 1, by chloroacetic chloride.
KL-18 white solids, yield 83%;1H NMR (400MHz, Chloroform-d) δ 8.21 (t, J=8.2Hz,
2H), 7.78 (s, 1H), 7.75 (t, J=8.4Hz, 1H), 1.47 (d, J=7.0Hz, 6H) .ESI-MS m/z:374.09[M+
Na]+.
Embodiment 19
KL-19 is synthesized:Experimental procedure is changed to 2- bromo propionyl chloros with embodiment 1, by chloroacetic chloride.
KL-19 white solids, yield 45%;1H NMR (400MHz, Chloroform-d) δ 8.60 (d, J=8.1Hz,
1H), 8.02 (d, J=7.5Hz, 1H), 7.52 (t, J=7.9Hz, 1H), 6.69 (d, J=1.9Hz, 1H), 4.87-4.74 (m,
2H), 2.06 (d, J=6.9Hz, 3H) .ESI-MS m/z:388.11[M+Na]+.
Embodiment 20
KL-20 is synthesized:Experimental procedure is changed to chloro-pivalyl chloride with embodiment 1, by chloroacetic chloride.
KL-20 white solids, yield 75%;1H NMR (400MHz, Chloroform-d) δ 8.28 (dd, J=8.5,
1.3Hz, 1H), 8.21 (d, J=7.3Hz, 1H), 7.77 (d, J=7.9Hz, 1H), 7.70 (s, 1H), 3.86 (s, 2H), 1.60
(s,6H).
ESI-MS m/z:422.07[M+Na]+.
Embodiment 21
KL-21 is synthesized:Experimental procedure is changed to isobutyryl chloride with embodiment 1, by chloroacetic chloride.
KL-21 white solids, yield 78%;1H NMR(400MHz,Chloroform-d)δ8.21(s,1H),8.19(s,
1H),7.78–7.71(m,2H),1.51(s,9H).ESI-MS m/z:388.11[M+Na]+.
Embodiment 22
KL-22 is synthesized:Experimental procedure is changed to ring propionyl chloride with embodiment 1, by chloroacetic chloride.
KL-22 white solids, yield 75%;1H NMR (400MHz, Chloroform-d) δ 8.20 (d, J=8.5Hz,
1H), 8.13 (d, J=7.3Hz, 1H), 7.72 (s, 1H), 7.69 (d, J=7.9Hz, 1H), 1.99 (tt, J=7.9,4.6Hz,
1H),1.30–1.22(m,2H),1.23–1.09(m,2H).ESI-MS m/z:372.07[M+Na]+.
Embodiment 23
KL-23 is synthesized:Experimental procedure is changed to ring butyl chloride with embodiment 1, by chloroacetic chloride.
KL-23 white solids, yield 73%;1H NMR (400MHz, Chloroform-d) δ 8.21 (dd, J=7.7,
5.4Hz, 2H), 7.80 (s, 1H), 7.74 (s, 1H), 3.62 (p, J=8.5Hz, 1H), 2.71-2.37 (m, 4H), 2.32-2.00
(m,2H).ESI-MS m/z:386.09[M+Na]+.
Embodiment 24
KL-24 is synthesized:Experimental procedure is changed to ring valeric chloride with embodiment 1, by chloroacetic chloride.
KL-24 white solids, yield 68%;1H NMR (400MHz, Chloroform-d) δ 8.22 (dd, J=13.5,
7.9Hz, 2H), 7.78 (s, 1H), 7.74 (s, 1H), 3.22 (p, J=8.0Hz, 1H), 2.21-2.13 (m, 3H), 2.11-2.02
(m,1H),1.89–1.82(m,2H),1.81–1.71(m,2H).ESI-MS m/z:400.11[M+Na]+.
Embodiment 25
KL-25 is synthesized:Experimental procedure is changed to Cyclohexanoyl chloride with embodiment 1, by chloroacetic chloride.
KL-25 white solids, yield 76%;1H NMR(400MHz,Chloroform-d)δ8.18–8.10(m,2H),
7.69 (s, 1H), 7.66 (d, J=7.9Hz, 1H), 2.72 (tt, J=11.3,3.7Hz, 1H), 2.20-2.07 (m, 2H), 1.83
(dt, J=12.9,3.6Hz, 2H), 1.76-1.54 (m, 3H), 1.33 (dtdd, J=29.2,17.0,7.7,4.4Hz, 3H)
.ESI-MS m/z:414.13[M+Na]+.
Embodiment 26
KL-26 is synthesized:Experimental procedure is changed to methacrylic chloride with embodiment 1, by chloroacetic chloride.
KL-26 white solids, yield 82%;1H NMR (400MHz, Chloroform-d) δ 8.22 (dd, J=11.6,
7.9Hz, 2H), 7.82 (s, 1H), 7.75 (s, 1H), 6.57 (s, 1H), 6.09-5.92 (m, 1H), 2.18 (t, J=1.3Hz,
3H).ESI-MSm/z:372.08[M+Na]+.
Embodiment 27
Indoor antibacterial determination of activity and result
1) experiment material:
Chemical formula KL-1~KL-26 quinoline derivatives synthesize for this laboratory.
Phytopathogen used in this experiment is the strain of the 4 DEG C of preservations in laboratory, and the culture medium used is trained for potato
Support base (abbreviation PDA).
PDA culture medium formula:Potato (peeling) 200g, glucose 20g, agar 15g, tap water 1000mL, natural PH.
Preparation method:Potato is cleaned into peeling, 200g is claimed to be cut into small pieces, adds boiling is rotten (to boil 20-30 minutes, energy quilt
Glass bar is poked), with eight layers of filtered through gauze in beaker, is needed to add 15-20g agar according to experiment, 20g grapes are added
Sugar stirs evenly, and slightly cooling water of supplying sterilizes 20 minutes for 121 DEG C to 1000mL after packing fully after dissolving, spare after cooling.
2) experimental method
Using growth rate method.
1, first by 5 kinds of phytopathogens, 25 DEG C of culture 6d or so are for use on PDA plate.
2, PDA culture medium heating is dissolved, is cooled to 45-50 DEG C, is separately added into the quinoline derivatives system of various concentration
At the culture medium containing 50,25,10,5 and 2.5 μ g/mL liquids, and pour into respectively cooling in culture dish.
3, it with sterile working formality, is beaten at each bacterial strain mycelia edge (upgrowth situation is consistent as possible) of culture 6d with card punch
Round bacteria cake (diameter 0.50cm) is taken, then is chosen to drug containing tablet center with transfer needle, culture dish is then inverted in incubator (25
DEG C) in culture.
4, after processing different time Observe and measure mycelia growing state, and measure diameter and locate using crossing method
Data are managed, inhibiting rate is calculated.
5, inhibiting rate (%)=(control hyphal diameter-processing hyphal diameter)/control hyphal diameter × 100
6, each processing is repeated 3 times.
3) quinoline derivatives are to cotton-wilt fusarium, fusarium graminearum, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn and rice
The fungistatic effect of seasonal febrile diseases bacterium mycelia growth
Cotton-wilt fusarium, fusarium graminearum, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn and Pyricularia oryzae are with reference to raw mark
Quasi- method NY/T1156.2-2006 carries out indoor biological determination of activity using growth rate method, specifies quinoline derivatives
Inhibitory activity of the KL-1~KL-26 to this five kinds of germs.Table 1 is quinoline derivatives to cotton-wilt fusarium, wheat scab
The inhibitory activity test result that bacterium, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn and Pyricularia oryzae mycelia grow.
1 quinoline derivatives of table to cotton-wilt fusarium, fusarium graminearum, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn and
The inhibitory activity test result of Pyricularia oryzae mycelia growth
Note:It each handles to set in experiment and repeat three times, data are the average value repeated three times in table, and "-" expression does not carry out
Bacteriostatic experiment.
Embodiment 28
Field control effect evaluation to Pumpkin powdery mildew and powdery mildew of cucumber.
1) Pumpkin powdery mildew
1, experiment material:Cucurbita pepo, kind ' advantage '.Monofilament shell powdery mildew (Sphaerotheca fuliginea
(Schl.) poll.) pick up from spontaneous bacterium source on Gansu Academy of Agricultural Science's temperature indoor pot cucurbita pepo.
2, control and reagent agent:Propiconazole, bulk myclobutanil, propiconazole, KL-1 compounds.
3, experimentation:
(1) sowing of cultivation management experimental plot, fertilizer and water management, the pervious insect pest preventing and controlling of experimental stage are consistent with local production.1
It is secondary
Other pesticides influential on powdery mildew are not applied before dispenser in 10d.
(2) bacterium method is connect:On September 16th, 2017, the fresh sick leaf of Pumpkin powdery mildew smash filtering to pieces, and spore suspension is in west
Cucurbit face of blade carries out even spraying and connects bacterium.
(3) medicament is arranged:15%KL-1 missible oil setting dilution 1500 times of liquid, 1 concentration, 12.5% nitrile bacterium azoles of comparison medicament
Breast
Oil and 25% propiconazole emulsifiable concentrate set dilution 1500 times of liquid, 1 concentration, separately set clear water control.
(4) application method:September in 2017 connects dispenser in 48 hours after bacterium on the 18th.Every dispenser in 7 days 1 time, continuous 3 (Septembers
18 days, September 25 days, October 3).
(5) investigation method:(October 21) investigation disease refers to 18 days after last 1 dispenser, calculates preventive effect.It investigates simultaneously
Safety.Disease severity grade scale is:
0 grade-disease-free spot;
1 grade-lesion area accounts for 2% or less leaf area;
3 grades-lesion area accounts for the 2%~5% of leaf area;
5 grades-lesion area accounts for the 6%~20% of leaf area;
7 grades-lesion area accounts for the 21%~40% of leaf area;
9 grades-lesion area accounts for 40% of leaf area or more.
(6) control effect
(7) 1500 times of liquid blades of safety evaluatio propiconazole thicken be hardened, the green, petiole that darkens shortens, growing point is bad
Extremely.The same propiconazole of nitrile bacterium azoles symptom of chemical damage only shows relatively light.KL-1 safety, blade variation without exception.
2) powdery mildew of cucumber
1, experiment material:Cucumber variety is the close thorn in Xintai City.Cucumber powdery mildew's pathogen (Sphaerotheca fuliginea) is adopted
From spontaneous bacterium source on Gansu Academy of Agricultural Science temperature indoor pot cucumber.
2, control and reagent agent:Bulk myclobutanil, propiconazole, Original Tebuconazole, difenoconazole, KL-1 chemical combination
Object.
3, experimentation:
(1) sowing of cultivation management experimental plot, fertilizer and water management, the pervious insect pest preventing and controlling of experimental stage are consistent with local production.
Other pesticides influential on powdery mildew of cucumber are not applied before 1 dispenser in 10d.
(2) bacterium method on October 7th, 2017 is connect, the fresh sick leaf of powdery mildew of cucumber smashs filtering to pieces, and spore suspension is in cucumber
Face of blade carries out even spraying and connects bacterium.
(3) medicament setting 15%KL-1 missible oil, 12.5% nitrile bacterium azoles missible oil, 25% propiconazole emulsifiable concentrate, 430g/L Tebuconazoles
Suspending agent, 25% difenoconazole missible oil are respectively provided with dilution 2500 times of liquid, 1 concentration (preparation dosage), separately set clear water control.
(4) application method temperature indoor pot cucumber, October 9 cucumber florescence powdery mildew initial phase (natural occurrence, put down
Equal disease index:0 grade 56,1 grade 35,3 grades 4,7 grades 1, disease referred to 6.25) the 1st dispenser of beginning, every dispenser 1 in 7 days
3 times secondary, continuous (on October 9,16,23 days), 10 days after the 3rd dispenser (November 2) by 9 grades classification standard surveys fall ill feelings
Condition calculates disease and refers to, and refers to calculating preventive effect according to disease.
(5) investigation on 10 days (November 22) disease refers to after last 1 dispenser of investigation method, calculates preventive effect.Investigate safety simultaneously
Property.Disease severity grade scale is:
0 grade-disease-free spot;
1 grade-lesion area accounts for 2% or less leaf area;
3 grades-lesion area accounts for the 2%~5% of leaf area;
5 grades-lesion area accounts for the 6%~20% of leaf area;
7 grades-lesion area accounts for the 21%~40% of leaf area;
9 grades-lesion area accounts for 40% of leaf area or more.
(6) control effect
(7) safety evaluatio propiconazole dispenser blade thicken be hardened, darken, petiole shortens, leaf margin not yellow;Penta
Azoles alcohol, nitrile bacterium azoles dispenser blade thicken and are hardened, and darken, petiole shortens, leaf margin yellow;Difenoconazole safety.KL-1 is applied
Medicine plant lobus cardiacus leaf margin last volume has irregularly withered hickie, and symptoms are mild.
Claims (3)
1. a kind of application of the quinolines of the present invention in controlling plant diseases, compound structure feature is such as
Under:
2. application of a kind of quinolines in preparing pathogenic bacteria inhibitor according to claim 1.
3. application according to claim 2, it is characterised in that:The plant disease is the plant caused by following pathogens
Disease:Cotton-wilt fusarium, gibberella saubinetii, Sclerotinia sclerotiorum, Rhizoctonia solani Kuhn, Pyricularia oryzae, Pumpkin powdery mildew and Huang
One or more of melon white powder arbitrarily combines.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810291712.1A CN108477170B (en) | 2018-03-30 | 2018-03-30 | Quinoline compound, preparation method thereof and application thereof in preventing and treating plant diseases |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810291712.1A CN108477170B (en) | 2018-03-30 | 2018-03-30 | Quinoline compound, preparation method thereof and application thereof in preventing and treating plant diseases |
Publications (2)
Publication Number | Publication Date |
---|---|
CN108477170A true CN108477170A (en) | 2018-09-04 |
CN108477170B CN108477170B (en) | 2020-07-14 |
Family
ID=63317834
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201810291712.1A Expired - Fee Related CN108477170B (en) | 2018-03-30 | 2018-03-30 | Quinoline compound, preparation method thereof and application thereof in preventing and treating plant diseases |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108477170B (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109467533A (en) * | 2018-12-14 | 2019-03-15 | 兰州大学 | A kind of 8-hydroxyquinoline class compound and preparation method thereof and the purposes in prevention and treatment agricultural disease |
CN110156678A (en) * | 2019-05-27 | 2019-08-23 | 兰州大学 | A kind of purposes of the derivatives of bis- (trifluoromethyl) the quinolines 4- modifications of 2,8- in controlling plant diseases |
CN110437146A (en) * | 2019-07-17 | 2019-11-12 | 兰州大学 | A kind of preparation of quinoline 4- hydroxy methacrylates class compound and its application in controlling plant diseases |
CN110938034A (en) * | 2018-09-21 | 2020-03-31 | 东莞市东阳光农药研发有限公司 | Quinoline derivatives and their use in agriculture |
CN112493244A (en) * | 2019-09-16 | 2021-03-16 | 兰州大学 | Application of quinoline 2-position derivative in preparation of agricultural plant disease prevention and treatment medicines |
CN112608275A (en) * | 2020-12-29 | 2021-04-06 | 兰州大学 | Application of 2, 8-bis (trifluoromethyl) -4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases |
CN112939942A (en) * | 2020-12-24 | 2021-06-11 | 聊城大学 | Heterocyclic ester compound containing quinoline structure and preparation method and application thereof |
CN114957116A (en) * | 2022-07-01 | 2022-08-30 | 浙江工业大学 | 2, 3-dimethyl-8-fluoroquinoline-4-ester compound and preparation method and application thereof |
CN115466212A (en) * | 2022-10-26 | 2022-12-13 | 河南农业大学 | 2-trifluoromethyl quinoline compound and synthetic method and application thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105994314A (en) * | 2016-07-13 | 2016-10-12 | 兰州大学 | Application of Luotonin A to prevention and treatment of aphid |
CN107711855A (en) * | 2017-09-11 | 2018-02-23 | 兰州大学 | Application of the peaceful alkali A derivatives of camel in the medicine of preventing and treating or anti-plant disease is prepared |
-
2018
- 2018-03-30 CN CN201810291712.1A patent/CN108477170B/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105994314A (en) * | 2016-07-13 | 2016-10-12 | 兰州大学 | Application of Luotonin A to prevention and treatment of aphid |
CN107711855A (en) * | 2017-09-11 | 2018-02-23 | 兰州大学 | Application of the peaceful alkali A derivatives of camel in the medicine of preventing and treating or anti-plant disease is prepared |
Non-Patent Citations (3)
Title |
---|
XIAO-FEI SHANG等: "Biologically active q uinoline and quinazoline alkaloids part I", 《MEDICINAL RESEARCH REVIEWS》 * |
XIAO-FEI SHANG等: "Biologically active q uinoline and quinazoline alkaloids part II", 《MEDICINAL RESEARCH REVIEWS》 * |
YE-FENG FAN等: "Facile three-component synthesis and insecticidal evaluation of hexahydroimidazo[1,2-a]pyridine derivatives", 《CHINESE CHEMICAL LETTERS》 * |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110938034A (en) * | 2018-09-21 | 2020-03-31 | 东莞市东阳光农药研发有限公司 | Quinoline derivatives and their use in agriculture |
CN110938034B (en) * | 2018-09-21 | 2021-05-11 | 东莞市东阳光农药研发有限公司 | Quinoline derivatives and their use in agriculture |
CN109467533A (en) * | 2018-12-14 | 2019-03-15 | 兰州大学 | A kind of 8-hydroxyquinoline class compound and preparation method thereof and the purposes in prevention and treatment agricultural disease |
CN110156678A (en) * | 2019-05-27 | 2019-08-23 | 兰州大学 | A kind of purposes of the derivatives of bis- (trifluoromethyl) the quinolines 4- modifications of 2,8- in controlling plant diseases |
CN110437146A (en) * | 2019-07-17 | 2019-11-12 | 兰州大学 | A kind of preparation of quinoline 4- hydroxy methacrylates class compound and its application in controlling plant diseases |
CN112493244A (en) * | 2019-09-16 | 2021-03-16 | 兰州大学 | Application of quinoline 2-position derivative in preparation of agricultural plant disease prevention and treatment medicines |
CN112939942A (en) * | 2020-12-24 | 2021-06-11 | 聊城大学 | Heterocyclic ester compound containing quinoline structure and preparation method and application thereof |
CN112939942B (en) * | 2020-12-24 | 2023-11-07 | 聊城大学 | Heterocyclic ester compound containing quinoline structure, and preparation method and application thereof |
CN112608275A (en) * | 2020-12-29 | 2021-04-06 | 兰州大学 | Application of 2, 8-bis (trifluoromethyl) -4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases |
CN114957116A (en) * | 2022-07-01 | 2022-08-30 | 浙江工业大学 | 2, 3-dimethyl-8-fluoroquinoline-4-ester compound and preparation method and application thereof |
CN115466212A (en) * | 2022-10-26 | 2022-12-13 | 河南农业大学 | 2-trifluoromethyl quinoline compound and synthetic method and application thereof |
CN115466212B (en) * | 2022-10-26 | 2023-09-22 | 河南农业大学 | 2-trifluoromethyl quinoline compound and synthetic method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN108477170B (en) | 2020-07-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108477170A (en) | A kind of quinolines and preparation method thereof and the purposes in controlling plant diseases | |
CN107711855B (en) | Application of camelinine A derivative in preparation of medicines for preventing and treating or resisting plant diseases | |
CN109467533A (en) | A kind of 8-hydroxyquinoline class compound and preparation method thereof and the purposes in prevention and treatment agricultural disease | |
CN109717198B (en) | Application of A-ring modified neohederazine derivative in prevention and treatment of agricultural plant diseases | |
CN110156678A (en) | A kind of purposes of the derivatives of bis- (trifluoromethyl) the quinolines 4- modifications of 2,8- in controlling plant diseases | |
CN110437146A (en) | A kind of preparation of quinoline 4- hydroxy methacrylates class compound and its application in controlling plant diseases | |
CN107721956B (en) | Benzobutyrolactone derivative, synthesis method and application thereof in preparing bactericide | |
CN109503562A (en) | 2- [4- (2- thienyl)] pyrimidine radicals urea derivative and its preparation method and application | |
CN109942561A (en) | 4- (2- thienyl) pyrimidine derivatives and its preparation method and application | |
CN111377870B (en) | 2, 4-dioxoimidazolines cyclohexane sulfonamide compounds, process for their preparation and their use as fungicides or bactericides | |
CN110372588B (en) | 4-aminoquinoline compound and preparation method and application thereof | |
CN111937886A (en) | Preparation of 8-hydroxyquinoline complex and application thereof in preventing and treating plant diseases | |
CN103524418B (en) | One group of 3-methylpyrazole compound | |
CN106220558B (en) | N-4- pyridine acyl-dehydroabietylamine derivatives and its preparation method and application | |
CN110447651B (en) | Quinazolinone compound and application thereof in preparation or prevention and treatment of agricultural plant diseases | |
CN103788119A (en) | Thiadiazole metal complex and application thereof in control of agricultural plant diseases | |
CN103232447A (en) | 3-acetyl-5-acetylimino-2-(N-phenothiazinyl)-1,3,4-thiadiazole, and preparation method and application thereof | |
CN103554026B (en) | One group of 3-trifluoromethyl-4-formyl pyrazole compound | |
CN110437099B (en) | Aromatic hydrazide compound and preparation method and application thereof | |
CN109535136A (en) | 2- [4- (2- furyl)] pyrimidine radicals carbamide compounds and its preparation method and application | |
CN106800534B (en) | A kind of cinnamic acid naphthalimide ester type compound and application thereof | |
CN114957215B (en) | Methylene bridged quinoline and 1,2, 3-triazole diheterocyclic compound and preparation method and application thereof | |
CN105541706B (en) | A kind of chloro- 2- diazanyls -5- trifluoromethyl pyridines derivative of 3- and its preparation and application | |
CN109897005B (en) | Phenyl pyrimidine analogue containing substituted phenoxy, preparation method and application thereof | |
CN113788800B (en) | Preparation method and application of 5-trifluoromethyl substituted oxadiazole compound containing diphenyl ether group |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20200714 Termination date: 20210330 |
|
CF01 | Termination of patent right due to non-payment of annual fee |