CN1204330A - 杂环杀菌剂 - Google Patents
杂环杀菌剂 Download PDFInfo
- Publication number
- CN1204330A CN1204330A CN96198881A CN96198881A CN1204330A CN 1204330 A CN1204330 A CN 1204330A CN 96198881 A CN96198881 A CN 96198881A CN 96198881 A CN96198881 A CN 96198881A CN 1204330 A CN1204330 A CN 1204330A
- Authority
- CN
- China
- Prior art keywords
- arh
- compound
- optionally substituted
- formula
- mixture
- 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
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 17
- 239000000417 fungicide Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000002252 acyl group Chemical group 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 239000001301 oxygen Chemical group 0.000 claims abstract description 8
- 125000004429 atom Chemical group 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 6
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 71
- -1 Benzyl Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 241000233866 Fungi Species 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract description 3
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 abstract 1
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 41
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000000284 extract Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 6
- PLQGWBZUQFSURJ-UHFFFAOYSA-N 6-bromo-4-chloro-3-propylchromen-2-one Chemical compound BrC1=CC=C2OC(=O)C(CCC)=C(Cl)C2=C1 PLQGWBZUQFSURJ-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229910015900 BF3 Inorganic materials 0.000 description 5
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 241000209094 Oryza Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 description 3
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241000233679 Peronosporaceae Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000001671 coumarin Nutrition 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- NRNFKRFWZQQDMD-UHFFFAOYSA-M dichloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=C(Cl)Cl NRNFKRFWZQQDMD-UHFFFAOYSA-M 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- HUTHNFFTMFGSDJ-UHFFFAOYSA-N 1-(4-bromo-2-hydroxyphenyl)pentan-1-one Chemical compound CCCCC(=O)C1=CC=C(Br)C=C1O HUTHNFFTMFGSDJ-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000005133 alkynyloxy group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004777 chromones Chemical class 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940125810 compound 20 Drugs 0.000 description 2
- 229940126208 compound 22 Drugs 0.000 description 2
- 229940125961 compound 24 Drugs 0.000 description 2
- 229940125851 compound 27 Drugs 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical class C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- AYDARZZGWLLFEX-UHFFFAOYSA-N (3-bromophenyl) pentanoate Chemical compound CCCCC(=O)OC1=CC=CC(Br)=C1 AYDARZZGWLLFEX-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- IXMJLAJRNXEJTQ-UHFFFAOYSA-N (4-bromophenyl) 2-(4-chlorophenyl)acetate Chemical compound C1=CC(Cl)=CC=C1CC(=O)OC1=CC=C(Br)C=C1 IXMJLAJRNXEJTQ-UHFFFAOYSA-N 0.000 description 1
- WHUOBOZCUKCBMA-UHFFFAOYSA-N (4-bromophenyl) 2-phenylacetate Chemical compound C1=CC(Br)=CC=C1OC(=O)CC1=CC=CC=C1 WHUOBOZCUKCBMA-UHFFFAOYSA-N 0.000 description 1
- SCJRDNZFWLRXDR-UHFFFAOYSA-N (4-bromophenyl) heptanoate Chemical compound CCCCCCC(=O)OC1=CC=C(Br)C=C1 SCJRDNZFWLRXDR-UHFFFAOYSA-N 0.000 description 1
- XDIFYXKFWPNGRV-UHFFFAOYSA-N (4-methylphenyl) pentanoate Chemical compound CCCCC(=O)OC1=CC=C(C)C=C1 XDIFYXKFWPNGRV-UHFFFAOYSA-N 0.000 description 1
- KRQNCNHFVJIFOO-UHFFFAOYSA-N (6-bromo-2-oxo-3-propylchromen-4-yl) n,n-diethylcarbamodithioate Chemical compound BrC1=CC=C2OC(=O)C(CCC)=C(SC(=S)N(CC)CC)C2=C1 KRQNCNHFVJIFOO-UHFFFAOYSA-N 0.000 description 1
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 description 1
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- NOEJTXWXNXGXQN-UHFFFAOYSA-N 1-(4-bromo-2-hydroxyphenyl)-2-[chloro(dimethylamino)methylidene]pentan-1-one Chemical compound CCCC(=C(Cl)N(C)C)C(=O)C1=CC=C(Br)C=C1O NOEJTXWXNXGXQN-UHFFFAOYSA-N 0.000 description 1
- NXARXMWFJHBSQB-UHFFFAOYSA-N 1-(5-bromo-2-hydroxyphenyl)-2-(4-chlorophenyl)ethanone Chemical compound OC1=CC=C(Br)C=C1C(=O)CC1=CC=C(Cl)C=C1 NXARXMWFJHBSQB-UHFFFAOYSA-N 0.000 description 1
- GVURCXUQMQBAFD-UHFFFAOYSA-N 1-(5-bromo-2-hydroxyphenyl)-2-phenylethanone Chemical compound OC1=CC=C(Br)C=C1C(=O)CC1=CC=CC=C1 GVURCXUQMQBAFD-UHFFFAOYSA-N 0.000 description 1
- IATLKSVXOSQVIQ-UHFFFAOYSA-N 1-(5-bromo-2-hydroxyphenyl)-3-chloro-3-(dimethylamino)-2-phenylprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(=C(Cl)N(C)C)C(=O)C1=CC(Br)=CC=C1O IATLKSVXOSQVIQ-UHFFFAOYSA-N 0.000 description 1
- HQCCNFFIOWYINW-UHFFFAOYSA-N 1-(5-bromo-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(Br)=CC=C1O HQCCNFFIOWYINW-UHFFFAOYSA-N 0.000 description 1
- UDHLQEFLGYLJDD-UHFFFAOYSA-N 1-(5-bromo-2-hydroxyphenyl)heptan-1-one Chemical compound CCCCCCC(=O)C1=CC(Br)=CC=C1O UDHLQEFLGYLJDD-UHFFFAOYSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical class C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- ZROILLPDIUNLSE-UHFFFAOYSA-N 1-phenyl-1h-pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC=CC=C1 ZROILLPDIUNLSE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
- PWQUWRNJTZVMCZ-UHFFFAOYSA-N 2,6-dimethoxy-3-propylchromen-4-one Chemical compound C1=C(OC)C=C2C(=O)C(CCC)=C(OC)OC2=C1 PWQUWRNJTZVMCZ-UHFFFAOYSA-N 0.000 description 1
- UMQUIRYNOVNYPA-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1 UMQUIRYNOVNYPA-UHFFFAOYSA-N 0.000 description 1
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 1
- NHLHEMXKFXSKHV-UHFFFAOYSA-N 2-(dimethylamino)-6-methoxy-3-propylchromen-4-one Chemical compound C1=C(OC)C=C2C(=O)C(CCC)=C(N(C)C)OC2=C1 NHLHEMXKFXSKHV-UHFFFAOYSA-N 0.000 description 1
- WNAJXPYVTFYEST-UHFFFAOYSA-N 2-Amino-3-methylbenzoate Chemical compound CC1=CC=CC(C(O)=O)=C1N WNAJXPYVTFYEST-UHFFFAOYSA-N 0.000 description 1
- UYDGECQHZQNTQS-UHFFFAOYSA-N 2-amino-4,6-dimethylpyridine-3-carboxamide Chemical compound CC1=CC(C)=C(C(N)=O)C(N)=N1 UYDGECQHZQNTQS-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
- XIQFRRICNGTFKG-UHFFFAOYSA-N 2-methoxy-6-methyl-3-phenylchromen-4-one Chemical compound COC=1OC2=CC=C(C)C=C2C(=O)C=1C1=CC=CC=C1 XIQFRRICNGTFKG-UHFFFAOYSA-N 0.000 description 1
- CHSGNSSBMXELKJ-UHFFFAOYSA-N 2-methoxy-6-methylchromen-4-one Chemical compound CC1=CC=C2OC(OC)=CC(=O)C2=C1 CHSGNSSBMXELKJ-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- VWQNKCBIQVYYPS-UHFFFAOYSA-N 3-bromo-2-methoxy-6-methylchromen-4-one Chemical compound C1=C(C)C=C2C(=O)C(Br)=C(OC)OC2=C1 VWQNKCBIQVYYPS-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- WIEGPFGKWNTTJC-UHFFFAOYSA-N 4-butoxy-6-methyl-3-propylchromen-2-one Chemical compound C1=CC(C)=CC2=C1OC(=O)C(CCC)=C2OCCCC WIEGPFGKWNTTJC-UHFFFAOYSA-N 0.000 description 1
- VYEJRHXLEHYKFO-UHFFFAOYSA-N 4-butoxy-8-methyl-3-propylchromen-2-one Chemical compound CC1=CC=CC2=C1OC(=O)C(CCC)=C2OCCCC VYEJRHXLEHYKFO-UHFFFAOYSA-N 0.000 description 1
- OQKKIDWORWDGKQ-UHFFFAOYSA-N 4-hydroxy-6-methyl-3-propylchromen-2-one Chemical compound CC1=CC=C2OC(=O)C(CCC)=C(O)C2=C1 OQKKIDWORWDGKQ-UHFFFAOYSA-N 0.000 description 1
- NKGBGJLEHWQNML-UHFFFAOYSA-N 4-hydroxy-8-methyl-3-propylchromen-2-one Chemical compound C1=CC(C)=C2OC(=O)C(CCC)=C(O)C2=C1 NKGBGJLEHWQNML-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 1
- JFBZVFQKVDWVLF-UHFFFAOYSA-N 6-bromo-2-(dimethylamino)-3-ethylchromen-4-one Chemical compound C1=C(Br)C=C2C(=O)C(CC)=C(N(C)C)OC2=C1 JFBZVFQKVDWVLF-UHFFFAOYSA-N 0.000 description 1
- VYYZNGKVXWAQTK-UHFFFAOYSA-N 6-bromo-2-(dimethylamino)-3-phenylchromen-4-one Chemical compound CN(C)C=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=CC=C1 VYYZNGKVXWAQTK-UHFFFAOYSA-N 0.000 description 1
- DANIPIQLQABHGU-UHFFFAOYSA-N 6-bromo-2-phenylmethoxy-3-propylchromen-4-one Chemical compound O1C2=CC=C(Br)C=C2C(=O)C(CCC)=C1OCC1=CC=CC=C1 DANIPIQLQABHGU-UHFFFAOYSA-N 0.000 description 1
- ZDGSMYLAKSUWPV-UHFFFAOYSA-N 6-bromo-2-sulfanylchromen-4-one Chemical compound BrC1=CC=C2OC(S)=CC(=O)C2=C1 ZDGSMYLAKSUWPV-UHFFFAOYSA-N 0.000 description 1
- CVYWPJYLWXGVOK-UHFFFAOYSA-N 6-bromo-3-(4-chlorophenyl)-2-methylsulfanylchromen-4-one Chemical compound CSC=1OC2=CC=C(Br)C=C2C(=O)C=1C1=CC=C(Cl)C=C1 CVYWPJYLWXGVOK-UHFFFAOYSA-N 0.000 description 1
- KZCAYXXFMWNOGC-UHFFFAOYSA-N 6-bromo-3-(5-bromothiophen-2-yl)-4-butoxychromen-2-one Chemical compound O=C1OC=2C=CC(Br)=CC=2C(OCCCC)=C1C1=CC=C(Br)S1 KZCAYXXFMWNOGC-UHFFFAOYSA-N 0.000 description 1
- FVNHDUNSDOZFBM-UHFFFAOYSA-N 6-bromo-3-(5-bromothiophen-2-yl)-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC(Br)=CC=2C(O)=C1C1=CC=C(Br)S1 FVNHDUNSDOZFBM-UHFFFAOYSA-N 0.000 description 1
- NKOJSNHOSBYGRX-UHFFFAOYSA-N 6-bromo-3-ethyl-2-(propan-2-ylamino)chromen-4-one Chemical compound C1=C(Br)C=C2C(=O)C(CC)=C(NC(C)C)OC2=C1 NKOJSNHOSBYGRX-UHFFFAOYSA-N 0.000 description 1
- UNAHBTOMWYLQGO-UHFFFAOYSA-N 6-bromo-3-ethyl-2-methylsulfanylchromen-4-one Chemical compound C1=C(Br)C=C2C(=O)C(CC)=C(SC)OC2=C1 UNAHBTOMWYLQGO-UHFFFAOYSA-N 0.000 description 1
- OTYCZAAJCPOTNZ-UHFFFAOYSA-N 6-bromo-3-ethyl-2-sulfanylchromen-4-one Chemical compound C1=C(Br)C=C2C(=O)C(CC)=C(S)OC2=C1 OTYCZAAJCPOTNZ-UHFFFAOYSA-N 0.000 description 1
- YZYCQWQFDSCICR-UHFFFAOYSA-N 6-bromo-4-(2-methoxyethylamino)-3-propylchromen-2-one Chemical compound BrC1=CC=C2OC(=O)C(CCC)=C(NCCOC)C2=C1 YZYCQWQFDSCICR-UHFFFAOYSA-N 0.000 description 1
- BZVYZHPNBCKSQK-UHFFFAOYSA-N 6-bromo-4-(4-methoxyphenoxy)-3-propylchromen-2-one Chemical compound C12=CC(Br)=CC=C2OC(=O)C(CCC)=C1OC1=CC=C(OC)C=C1 BZVYZHPNBCKSQK-UHFFFAOYSA-N 0.000 description 1
- ZQMUBGQZRHDHTH-UHFFFAOYSA-N 6-bromo-4-(butylamino)-3-propylchromen-2-one Chemical compound C1=CC(Br)=CC2=C1OC(=O)C(CCC)=C2NCCCC ZQMUBGQZRHDHTH-UHFFFAOYSA-N 0.000 description 1
- JDSGUOSWYCSGBP-UHFFFAOYSA-N 6-bromo-4-[butyl(methyl)amino]-3-propylchromen-2-one Chemical compound C1=CC(Br)=CC2=C1OC(=O)C(CCC)=C2N(C)CCCC JDSGUOSWYCSGBP-UHFFFAOYSA-N 0.000 description 1
- QXLZAUQDZXSBOK-UHFFFAOYSA-N 6-bromo-4-butoxy-3-pentylchromen-2-one Chemical compound BrC1=CC=C2OC(=O)C(CCCCC)=C(OCCCC)C2=C1 QXLZAUQDZXSBOK-UHFFFAOYSA-N 0.000 description 1
- NDOBDUPGIFCVNI-UHFFFAOYSA-N 6-bromo-4-butoxy-3-phenylchromen-2-one Chemical compound O=C1OC=2C=CC(Br)=CC=2C(OCCCC)=C1C1=CC=CC=C1 NDOBDUPGIFCVNI-UHFFFAOYSA-N 0.000 description 1
- LLECVAFIGGKDHK-UHFFFAOYSA-N 6-bromo-4-butylsulfanyl-3-propylchromen-2-one Chemical compound C1=CC(Br)=CC2=C1OC(=O)C(CCC)=C2SCCCC LLECVAFIGGKDHK-UHFFFAOYSA-N 0.000 description 1
- SNDYPRDZOHNKQK-UHFFFAOYSA-N 6-bromo-4-butylsulfinyl-3-propylchromen-2-one Chemical compound C1=CC(Br)=CC2=C1OC(=O)C(CCC)=C2S(=O)CCCC SNDYPRDZOHNKQK-UHFFFAOYSA-N 0.000 description 1
- AVZZSMFIILKAGE-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-pentylchromen-2-one Chemical compound BrC1=CC=C2OC(=O)C(CCCCC)=C(O)C2=C1 AVZZSMFIILKAGE-UHFFFAOYSA-N 0.000 description 1
- BZJHYZCPJGLGEQ-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-phenylchromen-2-one Chemical compound O=C1OC=2C=CC(Br)=CC=2C(O)=C1C1=CC=CC=C1 BZJHYZCPJGLGEQ-UHFFFAOYSA-N 0.000 description 1
- CRXWPILWJOBCFJ-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-propylchromen-2-one Chemical compound BrC1=CC=C2OC(=O)C(CCC)=C(O)C2=C1 CRXWPILWJOBCFJ-UHFFFAOYSA-N 0.000 description 1
- MBFAYPWMTQDWDG-UHFFFAOYSA-N 6-bromo-4-phenylmethoxy-3-propylchromen-2-one Chemical compound C12=CC(Br)=CC=C2OC(=O)C(CCC)=C1OCC1=CC=CC=C1 MBFAYPWMTQDWDG-UHFFFAOYSA-N 0.000 description 1
- GLFGHLCDDUDQQN-UHFFFAOYSA-N 6-methoxy-2-methylsulfanyl-3-propylchromen-4-one Chemical compound C1=C(OC)C=C2C(=O)C(CCC)=C(SC)OC2=C1 GLFGHLCDDUDQQN-UHFFFAOYSA-N 0.000 description 1
- GGOLJASEKSRRSM-UHFFFAOYSA-N 6-methoxy-2-methylsulfonyl-3-propylchromen-4-one Chemical compound C1=C(OC)C=C2C(=O)C(CCC)=C(S(C)(=O)=O)OC2=C1 GGOLJASEKSRRSM-UHFFFAOYSA-N 0.000 description 1
- MVURPLJGGBWPPP-UHFFFAOYSA-N 6-methyl-2-methylsulfanylchromen-4-one Chemical compound CC1=CC=C2OC(SC)=CC(=O)C2=C1 MVURPLJGGBWPPP-UHFFFAOYSA-N 0.000 description 1
- FXQYWDZAVNPYQR-UHFFFAOYSA-N 7-bromo-4-hydroxy-3-propylchromen-2-one Chemical compound C1=C(Br)C=C2OC(=O)C(CCC)=C(O)C2=C1 FXQYWDZAVNPYQR-UHFFFAOYSA-N 0.000 description 1
- VDWXKHAQHIFAMW-UHFFFAOYSA-N 7-bromo-4-propoxy-3-propylchromen-2-one Chemical compound C1=C(Br)C=CC2=C1OC(=O)C(CCC)=C2OCCC VDWXKHAQHIFAMW-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N Isophorone Natural products CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241001617088 Thanatephorus sasakii Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- QCJQWJKKTGJDCM-UHFFFAOYSA-N [P].[S] Chemical compound [P].[S] QCJQWJKKTGJDCM-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000001931 aliphatic group Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229950004394 ditiocarb Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- PMBGHMBDWGNJJE-UHFFFAOYSA-N ethyl 2-(5-bromothiophen-2-yl)-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CC=C(Br)S1 PMBGHMBDWGNJJE-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 125000004468 heterocyclylthio group Chemical group 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N o-cresotic acid Natural products CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 239000002157 polynucleotide Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/54—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 substituted in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
结构式(Ⅰ)的化合物具有杀菌活性,其中许多化合物是新的。式中,Z和Y之一是CO,另一个是C-W-R2,虚线表示为了满足价键需要而存在的双键,W是O,S(O)n,N(R3),N(R3)N(R4),N(R3)O,或ON(R3);R1是氢,或是一个可任意选择取代的烷基,烯基,炔基,环烷基,苯基或杂环基;R2,R3和R4可以是相同的,也可以是不相同的,它们的含义如R1,或是酰基,或是R2和R3,或是R2和R4,或是R3和R4,和连接它们的氮或氧一起形成可任意选择取代的环,这些环可以含有其它杂原子;每个X可以是相同的,也可以是与其它X不同的,它们是卤素,CN,NO2,SF5,B(OH)2,三烷基硅烷基,或基团E,OE或S(O)nE,此处E是含义如R2的基团,或是可任意选择取代的氨基;或者两个邻近的X和连接它们的其它原子一起,形成可任意选择取代的碳环或杂环;n是0,1或2;p是0至4。
Description
本发明的领域
本发明涉及用作杀菌剂的新的双环杂环化合物。
先有技术
具有杀菌活性的一些色酮,以及它们的异构体香豆素已有报道。
美国专利USP 4065574报道了具有杀菌活性的2-取代色酮,取代基为羟基等各种基团。
欧洲专利EP 567828报道了具有杀菌活性的苯基丙烯酸酯衍生物,其中,在苯环的2-位上有香豆素氧甲基或色酮氧甲基。本专利认为分子中的苯基丙烯酸酯部分是发毒基团。
美国专利USP 4380649报道了仅在4-位被异佛尔酮氧基取代的香豆素。
本发明的说明
现在我们已经发现一些色酮和香豆素具有特别有价值的杀菌特性。
其中,
Z和Y之一是CO,另一个是C-W-R2,虚线表示为了满足价键需要时存在的双键,
W是O,S(O)n,N(R3),N(R3)N(R4),N(R3)O,或ON(R3);
R1是氢,或可任意选择取代的烷基,烯基,炔基,环烷基,苯基或杂环基;
R2,R3和R4可以是相同的,也可以是不相同的,其含义同R1,或是酰基,或是R2和R3,或R2和R4,或R3和R4与连接它们的氮或氧一起形成可任意选择取代的环,该环可以含有其它杂原子;
每个X可以是相同的,也可以是不相同的,它们是卤素,CN,NO2,SF5,B(OH)2,三烷基硅烷基,或是E,OE或S(O)nE,其中E是含义如R2的基团,或是可任意选择取代的氨基;或是两个邻近的X与连接它们的其它原子一起形成可任意选择取代的碳环或杂环;
n是0,1或2;和
p是0至4,
附带条件:
a)当W是0时,R2不能是邻位取代的苄基,和
b)当p是0时,R1不能是氢。
本发明所包括的式Ⅰ的化合物中,许多化合物是新的。式中,Z和Y之一是CO,另一个是C-W-R2,虚线表示为了满足价键需要时存在的双键;
W是O,S(O)n,N(R3),N(R3)N(R4),N(R3)O,或ON(R3);
R1是可任意选择取代的烷基,烯基,炔基,环烷基或苯基;
R2,R3和R4可以是相同的,也可以是不相同的,其含义同R1,或是酰基,或是可任意选择取代的杂环,或是R2和R3,或R2和R4,或R3和R4与连接它们的氮或氧一起形成可任意选择取代的环,该环可以含有其它杂原子;
每个X可以是相同的,也可以是不相同的,它们是卤素,CN,NO2,SF5,B(OH)2,三烷基硅烷基或是E,OE或S(O)nE,其中E的含义如R2,或是可任意选择取代的氨基;或是两个邻近的X和连接它们的其它原子一起形成可任意选择取代的碳环或杂环;
n是0,1或2;和
p是1或2,一个X基是在6-位的。
附带条件:
a)当Z是CO和WR2是甲氧基时,R1不是1-甲基苄基或1,1-二甲基烯丙基,
b)当Z是CO和WR2是N(CH3)2时,两个X基团不能形成在5、6位稠合的苯并环,和
c)当Y是CO时,W-R2不是甲氧基。
在分子中的任一烷基,最好是1-10个碳原子,尤其是1-7个碳原子,特别是1-5个碳原子的烷基,可以是直链的或支链的烷基。
在分子中的任一烯基或炔基,可以是直链的或支链的,最好是2-7个碳原子的,例如烯丙基,乙烯基,丙炔基。
在分子中的任一环烷基,最好是3-7个碳原子的,特别是环丙烷基,环戊烷基,或环己烷基。
在任一烷基、烯基、炔基或环烷基上的取代基可以是卤素,氰基,三烷基硅烷基,可任意选择取代的烷氧基,可任意选择取代的烷硫基,羟基,硝基,可任意选择取代的氨基,酰基,酰氧基,可任意选择取代的苯基,可任意选择取代的杂环基,可任意选择取代的苯硫基,可任意选择取代的苯氧基,可任意选择取代的杂环氧基,可任意选择取代的杂环硫基或含硫基团的氧化衍生物。环烷基也可以被烷基取代。
所说的杂环基包括下述的杂芳基和非芳香杂环基。杂芳基一般指最多含有4个杂原子的5元或6元环,杂原子选自氮、氧和硫,也可以是苯并环。杂芳基的实例有噻吩、呋喃、吡咯、噻唑、噁唑、咪唑、异噻唑、异噁唑、吡唑、1,3,4-噁二唑、1,3,4-噻二唑、1,2,4-噁二唑、1,2,4-噻二唑、1,2,4-三唑、1,2,3-三唑、四唑、苯并[b]噻吩、苯并[b]呋喃、吲哚、苯并[c]噻吩、苯并[c]呋喃、异吲哚、苯并噁唑、苯并噻唑、苯并咪唑、苯并异噁唑、苯并异噻唑、吲唑、苯并噻二唑、苯并三唑、二苯并呋喃、二苯并噻吩、咔唑、吡啶、吡嗪、嘧啶、哒嗪、1,3,5-三嗪、1,2,4-三嗪、1,2,4,5-四嗪、喹啉、异喹啉、喹噁啉、喹唑啉、邻二氮杂萘、1,8-二氮杂萘、1,5-二氮杂萘、1,6-二氮杂萘、1,7-二氮杂萘、2,3-二氮杂萘、吡啶并嘧啶、嘌呤、蝶啶和衍生基团。
非芳香杂环基一般是最多含有3个杂原子的3、5、6或7元环,杂原子选自氮、氧的硫,例如环氧乙烷基、环硫乙烷基、噻唑啉基、二噁茂烷基、1,3-苯并噁嗪基、1,3-苯并噻嗪基、吗啉基、吡唑啉基、环丁砜基、二氢喹唑啉基、哌啶基、苯二甲酰亚氨基、四氢呋喃基、四氢吡喃基、吡咯烷基、二氢吲哚基、2-氧吡咯烷基、2-氧苯并噁唑啉-3-基、或四氢氮杂基。
出现在任一个苯基或杂环基上的取代基,可以是例如卤素、CN、NO2、SF5、B(OH)2、三烷基硅烷基、酰基、O-酰基或基团E、OE或S(O)nE,其含义如上述的R2,或是可任意选择取代的氨基;或在环上的两个邻近的基团和连接它们的原子一起形成一个碳环或杂环,这些环可以是类似地被取代的。
所说的酰基,包括含硫和含磷的酸,以及羰酸的残基。酰基的实例有-COR5、-COOR5、-CLNR5R6、-CON(R5)OR6、-COONR5R6、-CON(R5)NR6R7、-COSR5、-CSSR5、-S(O)qR5、-S(O)2OR5、-S(O)qNR5R6、-P(=L)(OR5)(OR6)或-COOR5,其中R5、R6和R7可以是相同的,也可以是不相同的,它们是氢,可任意选择取代的烷基,可任意选择取代的环烷基,可任意选择取代的环烯基,可任意选择取代的烯基,可任意选择取代的炔基,可任意选择取代的苯基或杂环基,或R5和R6,或R6和R7,与连接它们的原子一起形成环,q是1或2和L是O或S。
氨基可以被一个或2个可任意选择取代的烷基或酰基所取代,或两个取代基可以形成一个环,最好是5元至7元环,这些环可以被取代并可以含有其它杂原子,如吗啉。
p一般是1或2。
X最好是卤素;烷基,如C1-5烷基,特别是甲基;烯基,如C2-4烯基;炔基,如C2-4炔基,并可被三烷基硅烷基任意选择取代;烷氧基,如C1-5烷氧基,特别是甲氧基;卤烷氧基,如卤-C1-5烷氧基;烯氧基;如C2-4烯氧基;炔氧基;如C2-4炔氧基;环烷氧基,如C3-6环烷氧基;或烷硫基,如C1-5烷硫基,特别是甲硫基,或两个X基连在一起,形成一个甲撑二氧基。
W最好是O、S、SO、SO2、NH或N-烷基,如N-甲基。
R1最好是C3-6环烷基;C2-4烯基;苯基或烷基,如C1-6烷基,可任意被羟基,羟亚胺基、C1-6烷氧亚胺基或C1-6烷酰氧基取代。
R2最好是C3-6环烷基;苯基或烷基,如C1-6烷基,并可被C1-6烷氧基,C3-6环烷基或苯基任意选择取代。
在本发明的化合物中,X最好是在环上的6位,或6和8位上。
本发明也包括在实施例中所报道的化合物,但应除去WR2为羟基的化合物,这些化合物是作为中间体而合成的。
本发明的化合物具有杀菌活性,特别是可以防治植物的以下菌病,如霉病,特别是谷物白粉病、葡萄白粉病、葡萄霜霉病、稻瘟病、禾谷类眼斑病、稻纹枯病、灰霉病、茄苗丝核菌立枯病、隐匿柄锈病、蕃茄或马铃薯免疫病、苹果黑星病、麦类颖斑病。这些化合物具有活性的其它真菌有:其它白粉病,其它锈病,以及半知菌纲,子囊菌纲,藻状菌纲和担子菌纲病原菌引起的病害。
本发明也提供了在侵染点,或易被侵染的地点包括施用式Ⅰ化合物以防治真菌的方法。
本发明也提供了含有式Ⅰ化合物与农业上可接受的稀释剂或载体的农用组合物。
当然,本发明的组合物可以包含一种以上本发明的化合物。
另外,组合物也可以含有一种或更多种其它活性成分,如具有植物生长调节剂、除草剂、杀菌剂、杀虫剂或杀瞒剂性质的已知化合物。本发明的化合物也可与其它活性成分依次使用。
在本发明的组合物中的稀释剂和载体可以是固体或液体,并含有可任意选择的表面活性剂,如分散剂、乳化剂或湿润剂。适合的表面活性剂包括如羧酸根的阴离子化合物,例如长链脂肪酸的金属羧酸盐;N-酰基肌氨酸酯;磷酸与脂肪醇乙氧化物的单酯或双酯,或这些酯的盐;脂肪醇的硫酸酯,例如硫酸十二烷基酯钠,硫酸十八烷基酯钠或硫酸十六烷基酯钠;乙氧基化脂肪醇的硫酸酯;乙氧基化烷基酚的硫酸酯;木质素磺酸盐;石油磺酸盐;磺酸烷基-芳基酯,如磺酸烷基苯酯或磺酸低烷基萘酯,例如磺酸丁基萘酯;磺化萘-甲醛缩合物的盐;磺化酚-甲醛缩合物的盐;或更复杂的磺酸酯,如酰胺磺酸酯,例如油酸与N-甲基牛磺酸或磺基丁二酸二烷基酯的磺化缩合产物,丁二酸二辛酯的磺酸钠。非离子试剂包括脂肪酸酯、脂肪醇、脂肪酸酰胺或脂肪烷基-或烯基-取代的酚,与环氧乙烷、多元醇醚的脂肪酯,如山梨糖醇脂肪酸酯的缩合产物,这些酯与环氧乙烷的缩合产物,如聚氧乙撑山梨糖醇脂肪酸酯,环氧乙烷和环氧丙烷的嵌段共聚物,炔(属)乙二醇,如2,4,7,9-四甲基-5-癸炔-4,7-二醇或乙氧化炔(属)乙二醇。
阳离子表面活性剂包括例如乙酸,环烷酸或油酸的脂肪一胺、二胺或多胺的盐;含氧的胺,例如氧化胺,或多氧乙撑烷基胺;由脂肪酸与二胺,或多胺缩合生成的酰胺连接的胺;或季铵盐。
本发明的组合物可以采用任一种本技术领域熟知的农用化学品的剂型,例如溶液,分散剂,水乳剂,粉剂,浸种剂。熏蒸剂,烟剂,可分散性粉剂、乳油和颗粒剂。而且可以以适当的形式直接施用,或者作为一个浓制剂或初级组合物,在施用前用适量的水或其它稀释剂稀释后施用。
乳油的组成包括溶于与水不混溶溶剂中的本发明化合物,在乳化剂存在下,它能与水形成乳液。
粉剂的组成包括本发明的化合物以及与该化合物易混合的粉末状的固体填料,如高岭土。
颗粒剂的组成包括本发明的化合物和与粉剂中使用的,相类似的稀释剂,混合物以已知工艺进行造粒。此外,也可以是将活性成分吸附在预先造粒的稀释剂上,稀释剂的酸性白土,硅镁土或石灰石粒。
可温性粉剂,颗粒剂和细粒剂的组成通常有活性成分,与之混合的适当的表面活性剂以及惰性的粉剂稀释剂,如陶土。
另一个适当的浓制剂是浓悬浮剂,它是通过研磨化合物与水或其它液体,湿润剂和悬浮剂制成的。
本发明的组合物中的活性成分浓度,用于植物时,最好是0.0001~1.0%(重量),特别是0.0001~0.01%(重量)。在原始组合物中,活性成分的含量范围可以很宽,如组合物重量的5%~95%。
在本发明的方法中,化合物一般是施用于种子、植物或它们的栖息地。该化合物可在播种前播种时或播种后直接施于土壤,这样,在土壤里的活性成分就可以防止可能进攻种子的真菌的生长。在进行土壤直接处理时,只要活性化合物能与土壤充分混合,可用任一方式施用:如喷雾,撒播固体颗粒,或在播种的同时将活性成分与种子一同播入土壤中。适当的施药量范围是5~1000克/公顷,更合适的是10-500克/公顷。
此外,活性化合物也可以直接施用到植物上,例如真菌开始在植物上出现时,或是真菌出现之前,作为保护性措施,进行喷雾或喷粉。这两种情况下,最好的施用方式是叶面喷雾,为了获得防治真菌的良好的效果,重要的是要在植物生长的早期阶段用药,因为这时期的植物可能受到最严重的侵害。如果需要的话,喷雾或喷粉时可以含有一种芽前或芽后除草剂。有时在种植前或种植期间处理根部是可行的,例如在适当的液体或固体组合物中浸根。当活性化合物直接施于植物时,适当的用药量是0.025~5公斤/公顷,最好是0.05~1公斤/公顷。
本发明的新化合物可通过已知的多种方法来制备。典型的方法以如下反式图式所示。
式Ⅰ化合物的合成路线,式中Z为CO,Y为CWR2。
正如文献J.Org.Chem1960,25 677中所述,在无水氯化锌和氧氯化磷存在下,该反应可能受到加热的影响。如果反应试剂过量,在此过程中可能得到式Ⅴ的化合物。
此外,其中Y为CO,Z为COH的式Ⅰ化合物,可通过下法制得:式Ⅱ的酚先用通式为R1CH2COCl的酰氯酰化得到相应的酚酯,再重排成相应的通式Ⅳ的邻酰基酚,该反应通常在三氯化铝存在下,加热进行。然后,与三氟化硼醚化物反应生成式Ⅳ化合物的三氟化硼复合物,它与氯化二氯亚甲基二甲基铵反应生成相应的二甲胺基氯亚甲基化合物。然后在乙腈/水中环化生成式Ⅰ的化合物,Y为CO,Z为COH。
可是,由化合物Ⅳ环化生成其Y为CO,Z为COH的式Ⅰ化合物的反应,最好采用碳酸二乙酯和氢化钠来进行。
其中Y为CO,Z为COR2而R2不是氢的式Ⅰ化合物,可以在碱存在下通过上述化合物与通式R2Q的化合物反应制得,其中Q为离去基团,如卤素,或对甲苯磺酰氧基,或者通过与通式R2OH的醇,在Mitsunobu条件下(pph3,DEAD)反应制得。
式Ⅱ和Ⅲ的化合物或是已知的,或是可以通过已知的制备类似化合物的类似方法来制得其中Y为CO,Z为C-W-R2而W不是O的式Ⅰ的化合物,可以在碱存在下,由式Ⅴ的化合物与相应的亲核试剂,如R2SH,R2R3NH,R2R4NN(R3)H,R2ON(R3)H或R2R3NOH反应制得,其中R2-R4的含义如前所述。
其中Y为CO,Z为C-W-R2,W为N(R3)的式Ⅰ化合物,可以例如按Synfhesis 1987,303所述方法,由其中WR2为OH的式Ⅰ化合物与通式HNR2R3的胺反应制得。
式Ⅴ的化合物可由相应的其中WR2为OH的式Ⅰ化合物与氧氯化磷(Monatsh Chem,1986,117 1305-23)反应制得。
其中Y为CO,Z为C-W-R2和W为S的式Ⅰ的化合物,可以被氧化成W为SO或SO2的化合物。
其中Z为CO,Y为C-SH的式Ⅰ的化合物,可以在碱存在下,由式Ⅳ的化合物与硫化碳环化制得。
该化合物然后在碱存在下,通过已知的方法烷基化,酰基化,得到R2不是氢的化合物。
烷基化的化合物可以通过适当的方法氧化成Z为CO和Y为CS(O)nR2,n为1或2的化合物。式Ⅰ的化合物,其中Z为CO,Y为CH-W-R2和W不是硫,可以在碱存在下,从W为SO或SO2的化合物与相应的亲核试剂,如R2OH,R2R3NH,R2R4NN(R3)H,R2ON(R3)H或R2R3NOH反应制得,其中R2-R4的定义如前所述。所用的方法例如见J.Het.Chem1981,18,679。
此外,这些化合物也可以通过类似于以下文献报道的方法来制得,Chemistry and Industry 1980,116;J.ChemSoc.Chem.Com.11981,282和J.Org.Chem.1992,57,6502。
对于熟悉该技术领域的化学家来说,其它方法,包括制备起始原料和中间体的方法将是显而易见的。实例中也显然给出了制备本发明化合物以及起始原料和中间体的不同方法。
以下实例进一步阐明本发明,阐明本发明化合物以及羟基中间体的制备。
分离出的新化合物的结构已通过核磁共振谱和/或其它相应的分析方法给予证实。
实例1
在10℃,将2-乙酰基-4-溴酚(20克)和二硫化碳(7毫升)的甲苯(400毫升)溶液滴加到叔丁醇钾(31.4克)的甲苯(500毫升)悬浮液中。该混合物在室温下搅拌72小时。加入冰醋酸(35毫升),在减压下将该混合物蒸发。用水(200毫升)和冰醋酸(20毫升)处理残余物,沉淀出油状固体。加入石油醚(沸点40-60℃),混合物搅拌1小时,过滤,收集固体,用石油醚洗涤,得到6-溴-2-巯基-4H-1-苯并吡喃-4-酮,熔点230℃(化合物1)。
用类似的方法,制得6-溴-3-乙基-2-巯基-4H-1-苯并吡喃-4-酮(化合物1a)。
实例2
将化合物1a(1.8克)的丙酮(50亳升)溶液与碳酸钾(0.92克)搅拌和加碘甲烷(0.8毫升)。该混合物再搅拌15分钟,过滤,减压蒸发。残余物用乙酸乙酯溶解,用水洗该溶液,干燥,过滤,蒸发,残余物用石油醚(沸点40-60℃)研细,得到6-溴-3-乙基-2-甲硫基-4H-1-苯并吡喃-4-酮,熔点142~3℃(化合物2)。
实例3
将化合物2(1.44克)和二氯甲烷(10毫升)的溶液冷却至0℃,慢慢加入间氯过苯甲酸(20毫升)的无水二氯甲烷溶液(该溶液通过溶解50%纯度的原料1.66克于二氯甲烷中,再经硫酸镁干燥制得)。该混合物于0℃下搅拌过夜,用碳酸钠水溶液洗涤,干燥、蒸发。所得固体用乙酸乙酯研细,过滤,收集固体,得到6-溴-3-乙基-2-甲基亚磺酰基-4H-1-苯并吡喃-4-酮,熔点169~70℃(化合物3)。
实例4
采用类似于实例3的方法,用两倍化学计算量的间-氯过苯甲酸,6-甲氧基-2-甲硫基-3-丙基-4H-1-苯并吡喃-4-酮,得到6-甲氧基-2-甲基磺酰基-3-丙基-4H-1-苯并吡喃-4-酮,熔点153-155℃(化合物4)。
实例5
用异丙胺(1毫升)处理化合物3(0.3克)的乙腈溶液。该混合物于室温下搅拌过夜,减压蒸发,残余物经过硅胶色谱净化,然后用石油醚(沸点40-60℃)研细,得到6-溴-3-乙基-2-异丙胺基-4H-1-苯并吡喃-4-酮,熔点189-90℃(化合物5)。
实例6
将二甲胺通入化合物3(0.3克)的乙腈(5毫升)溶液中10分钟。该混合物在室温下搅拌过夜,减压蒸去溶剂。残余物经过硅胶色谱净化,得到6-溴-2-二甲胺基-3-乙基-4H-1-苯并吡喃-4-酮,熔点107-8℃(化合物6)。
实例7
将二甲胺通入化合物4(0.4克)的乙腈(20毫升)溶液中10分钟。将溶液减压蒸发,残余物溶解于二氯甲烷中。萃取液用盐水洗涤,干燥、过滤,蒸发,得到2-二甲胺基-6-甲氧基-3-丙基-4H-1-苯并吡喃-4-酮,棕色油(化合物7)。
实例8
将间-氯过苯甲酸(50%纯度,50.72克)溶解于二氯甲烷(250毫升)中,分去水,有机相用无水硫酸镁干燥。然后将该溶液于冷却下加到6-甲基-2-甲硫基-4H-1-苯并吡喃-4-酮(化合物110,见后)(10.13克)的二氯甲烷(50毫升)溶液中。该混合物于室温下搅拌过夜。加入在甲醇(250毫升)中的甲醇钠(20.11克),在室温下搅拌混合物1小时,然后减压蒸发。加入水(500毫升),用乙酸乙酯萃取混合物,萃取液用水洗涤,干燥,减压蒸发。产品在甲醇中重结晶,得到2-甲氧基-6-甲基-4H-1-苯并吡喃-4-酮,熔点166-7℃(化合物8)。
实例9
将甲醇钠(0.08克)加到化合物4(0.4克)的无水甲醇(8毫升)溶液中。该混合物搅拌5分钟。减压下蒸去溶剂,加入水。收集固体物质,干燥,得到2,6-二甲氧基-3-丙基-4H-1-苯并吡喃-4-酮,熔点78-80℃(化合物9)。
实例10
在搅拌下,将N-溴丁二酰亚胺(3.97克)加到化合物8(3.85克)的二氯甲烷(50毫升)溶液中,该混合物搅拌3小时。加入水(200毫升)并用二氯甲烷萃取混合物。萃取液用水洗涤,硫酸镁干燥,减压蒸发。残余物用甲苯重结晶,得到3-溴-甲氧基-6-甲基-4H-1-苯并吡喃-4-酮,熔点158-66℃(化合物10)。
实例11
将化合物10(0.51克)苯基硼酸(0.25克),四(三苯基膦)钯(O)(0.11克),碳酸钾(1.05克),甲苯(6毫升),乙醇(2毫升)和水(4毫升)的混合物,加热回流过夜,冷却,加到水中并用乙酸乙酯萃取。萃取液用水洗,干燥,蒸发,残余物用硅胶柱色谱净化,然后用石油醚(沸点40-60℃)研细,得到2-甲氧基-6-甲基-3-苯基-4H-1-苯并吡喃-4-酮,熔点112-5℃(化合物11)。
实例12
将苯乙酰氯(9.4克)滴加到4-溴苯酚(10克)的吡啶溶液中,反应混合物在室温下搅拌1小时,然后减压蒸发至干。残余物用乙酸乙酯萃取,水洗,硫酸镁干燥,过滤,减压蒸发,得到苯乙酸4-溴苯基酯。
将三氯化铝(5.5克)在搅拌下分批加到上述化合物(8克)中。将反应混合物加热到160℃,1小时。将所产生的热的粘油倒入冰/浓盐酸(100毫升)中,水相用二氯甲烷萃取。有机层用盐水洗涤2次,硫酸镁干燥,过滤,蒸发,得到5′-溴-2′-羟基-2-苯基苯乙酮。
将三氟化硼醚合物(1.6毫升)加到在乙醚(30毫升)中的上述产品(3.2克)中,反应混合物搅拌1小时,然后真空除去乙醚,得到三氟化硼复合物。
将二氯亚甲基-二甲基氯化铵(1.8克)加到在二氯乙烷(45毫升)中的上述产品(3.2克)中。将反应混合物加热到80℃,2小时,然后冷却,真空除去溶剂,得到5′-溴-2-〔氯(二甲胺基)亚甲基〕-2′-羟基-2-苯基苯乙酮的三氟化硼复合物。
将乙腈/水(5∶1)加到上述产品中,将反应混合物加热到50℃,1小时。然后真空除去溶剂,用乙醚将固体物研细,过滤,在空气中干燥,得到6-溴-2-二甲胺基-3-苯基-4H-1-苯并吡喃-4-酮,熔点118-120℃(化合物12)。
实例13
将戊酰氯(12.7克)滴加到在吡啶(50毫升)中的3-溴酚(9.0克)中,反应混合物在室温搅拌1小时。按实例12所述的后处理,得到戊酸3-溴苯酯。
将三氯化铝(12.74克)在搅拌下分批加到上述产品(16.5克)中,反应混合物加热到160℃,1小时。将所产生的热的粘油倒入冰/浓盐酸(100毫升)中,水相用二氯甲烷萃取,用盐水洗涤2次,硫酸镁干燥,过滤,蒸发,得到1-(4-溴-2-羟苯基)1-戊酮。
将三氟化硼醚合物(3.75克)加到在乙醚(30毫升)中的上述产品(6.5克)中,反应混合物搅拌1小时,然后减压除去乙醚,得到1-(4-溴-2-羟苯基)-1-戊酮的三氟化硼复合物。
将二氯亚甲基-二甲基氯化铵(4.4克)加到在二氯乙烷(50毫升)中的上述产品(8.0克)中。反应混合物加热至80℃,2小时,然后冷却,减压下除去溶剂,得到1-(4-溴-2-羟苯基)-2-[氯-(二甲胺基)亚甲基]-1-戊酮的三氟化硼复合物。
将乙腈/水(5∶1,60毫升)加到上述产品(7.0克)中,该反应混合物加热到50℃,1小时。然后减压下除去溶剂,用乙醚将固体物研细,过滤,在空气中干燥,得到7-溴-4-羟基-3-丙基-2H-苯并吡喃-2-酮,熔点138-40℃(化合物13)。
用类似的方法得到6-溴-4-羟基-3-丙基-2H-苯并吡喃-2-酮,熔点216-8℃(化合物13a)。
实例14
将在丙酮(5毫升)中的化合物13(0.5克),溴丙烷(0.23克)和碳酸钾(0.22克)的混合物回流过夜,然后减压除去溶剂,残余物用乙醚萃取,水洗,盐水洗,硫酸镁干燥,过滤,蒸发,得到7-溴-4-丙氧基-3-丙基-2H-苯并吡喃-2-酮,熔点73-5℃(化合物14)。
实例15
将1-丁硫醇(0.39毫升)滴加到钠(0.08克)的乙醇(3毫升)溶液中。该溶液搅拌半小时,然后慢慢加到回流的6-溴-4-氯-3-丙基-2H-1-苯并吡喃-2-酮(1克)在乙醇(4毫升)的溶液中。该混合物加热回流4.5小时,通过硅藻土热滤,冷却滤液。沉淀物通过硅胶色谱柱净化,得到6-溴-4-丁硫基-3-丙基-2H-1-苯并吡喃-2-酮,熔点62-4°(化合物15)。
原料的制备
将三丁基胺(12毫升)滴加到搅拌下的化合物13a(5克)和氯化磷酰(80.2毫升)在甲苯(50毫升)中的混合物中。该混合物在100-10℃加热过夜,然后倒入冰水中并用乙酸乙酯萃取。萃取液用水、盐水洗涤,干燥,蒸发。残余物通过硅胶色谱柱净化,得到6-溴-4-氯-3-丙基-2H-1-苯并吡喃-2-酮,熔点96-7℃。
实例16
用二乙基二硫代氨基甲酸钠(0.34克)处理6-溴-4-氯-3-丙基-2H-1-苯并吡喃-2-酮(0.5克)的二甲基甲酰胺(2毫升)溶液。该混合物于室温和氮气保护下搅拌过夜,然后倒入水中,用乙醚萃取。萃取液用盐水洗涤,干燥,减压蒸发,得到6-溴-4-二乙基硫代氨基甲酰基硫-3-丙基-2H-1-笨并吡喃-2-酮,熔点135-7°(化合物16)。
实例17
将丁胺(3毫升)与化合物13a(0.5克)的混合物加热回流45分钟。将该混合物溶于甲醇,加入氢氧化钠水溶液(0.1摩尔),再加热回流混合物36小时。再加入丁胺(10毫升),该混合物在压力容器内于100℃加热20小时。用乙酸乙酯稀释反应混合物,萃取液用水洗涤,干燥,减压蒸发。残余物通过硅胶色谱净化,得到6-溴-4-丁胺基-3-丙基-2H-1-苯并吡喃-2-酮,熔点153-4°(化合物17)。
实例18
将6-溴-4-氯-3-丙基-2H-1-苯并吡喃-2-酮(0.4克)和N-甲基丁胺(3毫升)的二甲基甲酰胺(2毫升)溶液加热回流30分钟,然后冷却过夜。蒸发,经柱色谱分离,得到6-溴-4-(丁基甲基氨基)-3-丙基-2H-1-苯并吡喃-2-酮,油状物(化合物18)。
实例19
在0℃,将间-氯过苯甲酸(0.29克,50%水悬浮液)加到化合物15(0.3克)的二氯甲烷(3毫升)溶液中。该混合物温热至10℃,用二氯甲烷稀释,用碳酸氢钠水溶液洗涤,干燥,蒸发。用石油醚研细,得到6-溴-4-丁基亚磺酰基-3-丙基-2H-1-苯并吡喃-2-酮,熔点122-3℃(化合物19)。
实例20
在室温和氮气保护下,将6-溴-4-氯-3-丙基-2H-1-苯并吡喃-2-酮(0.5克)与在干燥二甲基甲酰胺(5毫升)中的氢化钠(0.8克,在油中,60%含量)和4-甲氧基酚(0.24克)混合物搅拌过夜。然后将该混合物倒入稀盐酸中,用乙醚萃取。萃取液用氢氧化钠、盐水洗涤,干燥,减压蒸发。残余物用石油醚(沸点40-60℃)研细,得到6-溴-4-(4-甲氧基苯氧基)-3-丙基-2H-1-苯并吡喃-2-酮,熔点104-6℃(化合物20)。
用类似的方法制得6-溴-4-苯硫基-3-丙基-2H-1-苯并吡喃-2-酮,熔点84-5℃(化合物20a)。
实例21
先将三乙胺加到6-溴-4-氯-3-丙基-2H-1-苯并吡喃-2-酮(0.5克)的无水乙醇(10毫升)溶液中,然后加入2-乙氧基乙胺(0.16毫升)。该混合物在氮气保护下加热回流过夜,蒸发,残余物用乙酸乙酯萃取,萃取液用稀盐酸,盐水洗涤,干燥,减压蒸发。残余物用乙醇和石油醚(沸点40-60℃)研细,得到6-溴-4-(2-甲氧基乙胺基)-3-丙基-2H-1-苯并吡喃-2-酮,熔点75-7℃(化合物21)。
实例22
在0℃和搅拌下,将3-甲基邻氨基苯甲酸(12.5克)慢慢加到硫酸(61毫升,7.5克分子)中。维持在5℃以下,滴加亚硝酸钠(5.7克)水(19毫升)溶液。该混合物在室温搅拌半小时,在79-80℃加热1小时,然后冷却。加入水,放置过周末。过滤该混合物,收集沉淀,用水洗涤。将固体溶解在乙酸乙酯中,用水洗涤该溶液,并与氯化钡一起搅拌2小时以除去任何残留的硫酸,过滤,水洗,干燥,减压蒸发,得到3-甲基水杨酸,熔点160-2℃。
用丁基锂(92毫升,2.5摩尔的己烷溶液)处理上述化合物(10.6克)的四氢呋喃(60毫升)溶液。丁基锂加入的速度以维持回流为度。在氮气保护下继续加热回流过夜,冷却,倒入6N盐酸,冰和氯化钠的混合物中,用乙酸乙酯萃取该混合物,萃取液用盐水洗涤,干燥,减压蒸发,残余物用石油醚(沸点40-60℃)研细。过滤该混合物,滤液减压蒸发,得到2′-羟基-3′-甲基戊苯酮(valerophenone)为一种棕色的胶体。
将该化合物(6克)溶解于碳酸二乙酯(20毫升)中,再将该溶液滴加到搅拌下的氢化钠(3.75克,在油中浓度60%)的碳酸二乙酯(21.5毫升)悬浮液中。将该混合物在氮气保护下缓慢加温至120℃,3.5小时,冷却,倒入水中,酸化至pH1,搅拌1小时,放置过夜。过滤该混合物,用水和环己烷洗涤。将固体溶解在乙酸乙酯中,用水洗涤该溶液,干燥,减压蒸发,得到4-羟基-8-甲基-3-丙基-2H-1-苯并吡喃-2-酮,熔点180-2℃(化合物22)。
实例23
在氮气保护下,将在二甲基甲酰胺(5毫升)中的化合物22(1克),碳酸钾(0.76克)和1-溴丁烷(0.59毫升)的混合物搅拌过夜。减压下蒸出溶剂,残余物用乙酸乙酯萃取。萃取液用水洗涤,干燥,蒸发,残余物通过硅胶色谱柱净化,得到4-丁氧基-8-甲基-3-丙基-2H-1-苯并吡喃-2-酮,熔点35-7℃(化合物23)。
实例24
将4-溴酚(20克)无水吡啶(75毫升)溶液冷却到0℃,再滴加入庚酰氯(18.79毫升)。该混合物在室温搅拌2.5小时,加水(10毫升)溶解沉淀物,然后将该混合物进行减压蒸发。残余物溶解于乙醚中,用水,盐酸,水,饱和碳酸氢钠水溶液,水洗涤,干燥,减压蒸发,得到4-溴苯基庚酸酯。
将三氯化铝(22.44克)一份一份加到上述化合物(32克)中,在油浴上将该混合物加热到160℃,3.5小时。然后冷至室温,搅拌下倒入冰/1克分子盐酸(600毫升)中。加入二氯甲烷,水层用二氯甲烷萃取。合并的萃取液用水洗涤,干燥,减压蒸发,得到4-溴-2-庚酰基酚,为棕色油。以类似于实例22的方法,用在碳酸二乙酯中的氢化钠处理该化合物,得到6-溴-4-羟基-3-戊基-2H-1-苯并吡喃-2-酮,熔点176-8℃(化合物24)。
以类似于实例23的方法,用1-溴丁烷处理,可得到6-溴-4-丁氧基-3-戊基-2H-1-苯并吡喃-2-酮,熔点56-8℃(化合物24a)。
实例25
用在二氯甲烷(50毫升)中的4-氯苯基乙酰氯(3.3克)处理冷的(10℃),在搅拌下的4-溴酚(3克)和三乙胺(2.5毫升)的二氯甲烷(100毫升)溶液。将该混合物于室温下搅拌过夜。用水洗涤该溶液,硫酸镁干燥,过滤,减压蒸发。残余物通过硅胶色谱净化,得到4-氯苯基乙酸4-溴苯酯。
将上述化合物(5.8克)和三氯化铝的邻二氯苯溶液搅拌并加热至130℃,2小时。冷至室温,小心地倒入冷的稀盐酸(500毫升)中。用二氯甲烷萃取混合物,分出有机层,用硫酸镁干燥,色谱净化,得到5′-溴-2′-羟基-2-(4-氯苯基)乙酰苯,一种白色固体。
用二硫化碳处理上述化合物(5.1克)的无水甲苯(100毫升)溶液。将该混合物冷至大约10℃,并在维持温度的情况下加入特丁醇钾(6克)。在室温下,将该混合物搅拌过夜。用冰醋酸酸化,减压下蒸发至干。残余物用水(100毫升)处理,搅拌1小时。过滤沉淀物,用五氧化磷干燥,得到6-溴-2-巯基-3-(4-氯苯基)-4H-1-苯并吡喃-2-酮(化合物25)。
在室温下,将上述化合物(2.1克)置于无水丙酮(100毫升)中,与碳酸钾(0.5克)一起搅拌15分钟。加入碘甲烷,在蒸干前继续搅拌2小时。残余物分配在二氯甲烷和水中。分出有机相,硫酸镁干燥,过滤,减压蒸发。残余物用甲苯结晶,得到6-溴-2-甲硫基-3-(4-氯苯基)-4H-1-苯并吡喃-4-酮,熔点205-6℃。
实例26
在冰冷却下,将在二氯甲烷(50毫升)中的戊酰氯(39.8克)慢慢加到对甲苯酚(32.4克)和三乙胺(36.4克)的二氯甲烷(250毫升)溶液中。1小时后,用盐水洗涤反应混合物,硫酸镁干燥,过滤,减压蒸发,得到戊酸4-甲基苯酯。
将三氯化铝(45克)慢慢加到前述化合物(43克)的邻二氯苯(100毫升)溶液中。将该混合物加热至165℃,2.5小时,然后冷却过夜。将该混合物倒入含浓盐酸(40毫升)的冰(600毫升)中,搅拌至冰融化。用二氯甲烷萃取混合物,萃取液用盐水洗涤,硫酸镁干燥,减压蒸发,得到2′-羟基-4′-甲基戊酰苯,为二氯苯溶液。
在室温下将将前述溶液(84克,相当于20克化合物)慢慢加到氢化钠(12.5克,在油中的60%分散液)在碳酸二乙酯(125毫升)中的悬浮液中。将该混合物加热回流3小时,冷至室温,慢慢倒入冰/水中。分出有机层,水层用二氯甲烷洗涤,水层用浓盐酸酸化,过滤收集沉淀物,得到4-羟基-6-甲基-3-丙基-2H-1-苯并吡喃-2-酮,熔点184-6℃(化合物26)。
用实例23类似的方法,用1-溴丁烷处理该产品,得到4-丁氧基-6-甲基-3-丙基-2H-苯并吡喃-2-酮,熔点49℃(化合物26a)。
实例27
在4℃和搅拌下,将三氯化钛(7.71克)的水(50毫升)溶液加到(5-溴-2-噻吩基)二羟醋酸乙酯(5.0克)和5-溴-2-羟基苯甲醛(4.36克)的无水醋酸(50毫升)溶液中,继续搅拌该混合物1.5小时。用乙酸乙酯提取反应物,提取液用水、盐水洗涤,硫酸镁干燥,减压蒸发。将残留物溶于甲苯中并加对-甲苯磺酸(2.5g),加热回流混合物2.5小时。在室温下放置过夜,减压蒸发。残余物用硅胶柱色谱净化,得到6-溴- 3-(5-溴-2-噻吩基)-4-羟基-2H-1-苯并吡喃-2-酮,熔点234-6℃(化合物27)。
实例28
将碳酸钾(0.2克)和溴丁烷(0.11毫升)加到化合物27(0.25克)的二甲基甲酰胺(5毫升)溶液中,将该混合物加热至75℃,2.5小时。加入溴丁烷(0.11毫升),该混合物于室温放置2天。加入水(20毫升),用乙酸乙酯萃取。萃取液干燥,减压蒸发。残余物通过硅胶色谱柱净化,得到6-溴-3-(5-溴-2-噻吩基)-4-丁氧基-2H-1-苯并吡喃-2-酮,熔点104-5℃(化合物28)。
实例29
搅拌下,将溴丁烷(0.05毫升)加到6-溴-4-羟基-3-苯基-2H-1-苯并吡喃-2-酮(80毫克)(Synthesis 1993,99)的无水二甲基甲酰胺(0.5毫升)溶液和碳酸钾(70毫克)的混合物中。将该混合物搅拌48小时,加入水(5毫升),用乙醚萃取该混合物,萃取液用水洗涤,干燥,减压蒸发。残余物用水洗涤,干燥,得到6-溴-4-丁氧基-3-苯基-2H-1-苯并吡喃-2-酮,熔点87-9℃(化合物29)。
实例30
在室温和氮气保护下,将偶氮二羧酸二乙酯(0.83毫升,5.3毫摩尔)的无水四氢呋喃(3.5毫升)溶液慢慢加到化合物13a(1克),三苯基膦(1.39克)和苄醇(10.55毫升)的四氢呋喃(14毫升)溶液中。将该混合物搅拌4小时,减压蒸发。残余物通过硅胶色谱柱净化,得到4-苄氧基-6-溴-3-丙基-2H-1-苯并吡喃-2-酮,熔点121-3℃(化合物30a)和2-苄氧基-6-溴-3-丙基-4H-1-苯并吡喃-4-酮,熔点50-2℃(化合物30b)。
前述各实例中熔点没有被利用的化合物,它们的核磁共振资料如下:
Cod 1HNMR(CDCl3)
18 2构象异构体0.95(6H,m,2xCH3),1.2-1.65(4H,m,2xCH2),2.0(2H,m,CH2),2.95 and 3.1(3H,s,CH3),3.15 and 3.5(2H,m,CH2),4.2-4.4(2H,m,CH2)6.9(1H,d,ArH),7.5(1H,dd,ArH),7.7 and 7.85(1H,d,ArH)
45 1.0(6H,m,2xCH3),1.4(2H,m,CH2),1.58(2H,m,CH2)1.7(2H,m,CH2),2.55(2H,m,CH2),3.1(3H,s,NCH3)3.4(2H,t,CH2),7.18(1H,d,ArH),7.6(1H,dd,ArH)8.28(1H,d,ArH)
58 0.98(6H,m,2xCH3),1.58(2H,m,CH2),1.7(2H,m,CH2)2.55(2H,m,CH2),3.1(3H,s,NCH3),3.35(2H,t,CH2)7.15(1H,d,ArH),7.58(1H,dd,ArH),8.28(1H,d,ArH)
61 0.9(3H,t,CH3),1.0(3H,t,CH3),1.25-1.6(6H,m,3xCH2),1.8(2H,m,CH2),2.5(2H,t,CH2),4.4(2H,t,OCH2),7.17(1H,d,ArH),7.65(1H,dd,ArH),8.3(1H,d,ArH)
62 0.9(3H,t,CH3),1.1(3H,t,CH3),1.4(4H,m,2xCH2)1.8(2H,m,CH2),2.5(2H,q,CH2),4.4(2H,t,OCH2)7.25(1H,d,ArH),7.65(1H,dd,ArH), 8.35(1H,d,ArH)
63 0.9(3H,t,CH3),1.4(3H,t,CH3),1.6(6H,m,3xCH2)2.6(2H,t,CH2),4.15(2H,q,OCH2),7.25(1H,d,ArH)7.6(1H,dd,ArH),7.8(1H,d,ArH)
76 2.9(3H,s,SOCH3),7.2(2H,m,2ArH),7.4(3H,m,3ArH)7.6(1H,d,ArH),7.8(1H,dd,ArH),8.4(1H,d,ArH)
85 0.82(3H,t,CH3),1.35(3H,t,CH3),1.4(2H,m,CH2)2.32(3H,s,ArCH3),2.38(2H,m,CH2),4.4(2H,q,OCH2)7.15(1H,d,ArH),7.25(1H,dd,ArH),7.9(1H,d,ArH)
89 0.9(6H,t,2xCH3),1.35(3H,d,CH3),1.4(2H,m,CH2)1.7(2H,m,CH2),2.4(2H,t,CH2),4.95(1H,m,CH)7.2(1H,d,ArH),7.6(1H,dd,ArH),8.25(1H,d,ArH)
90 0.85(3H,t,CH3),1.4(2H,m,CH2),2.4(2H,t,CH2)2.5(2H,m,CH2),4.4(2H,t,CH2),5.1(2H,t,CH2)5.8(1H,m,CH),7.15(1H,d,ArH),7.6(1H,dd,ArH)8.25(1H,d,ArH)
93 0.95(3H,t,CH3),1.5(2H,m,CH2),1.7-2.1(4H,m,2×CH2)2.5(2H,t,CH2),3.9(2H,m,CH2),4.3(1H,m,CH),4.4(2H,d,OCH2)7.25(1H,d,ArH),7.65(1H,dd,ArH),8.3(1H,d,ArH)
111 0.9(3H,t,CH3),1.6(2H,m,CH2),2.6(2H,m,CH2),3.3(2H,t,CH2)3.4(3H,s,OCH3),3.7(2H,t,CH2),7.3(1H,m,ArH),7.7(1H,m,ArH)8.3(1H,d,ArH)
125 3.52(3H,s,SO2CH3),7.0(1H,s,CH),7.82(1H,d,ArH)8.1(1H,dd,ArH),8.18(1H,d,ArH)
128 1.0(3H,t,CH3),1.5(2H,m,CH2),2.5(2H,m,CH2)4.1(3H,s,OCH3),7.4(1H,d,ArH),7.8(1H,d,ArH)8.5(1H,s,ArH)
133 1.0(3H,t,CH3),1.6(2H,m,CH2),2.8(2H,m,CH2)5.2(2H,s,OCH2),6.9(1H,d,ArH),7.2(1H,d,ArH)7.4(6H,s,ArHx6),9.9(1H,bs,SH)
134 1.0(3H,t,CH3),1.5(2H,m,CH2),2.5(2H,m,CH2)2.6(3H,s,SCH3),5.2(2H,s,OCH2),6.8(1H,d,ArH)6.9(1H,d,ArH),7.3(1H,m,ArH),7.4(3H,m,3xArH)7.6(2H,d,2xArH)
135 1.1(3H,t,CH3),1.6-1.7(2H,m,CH2),2.9(2H,m,CH2),3.2(3H,s,SO2CH3),5.2(2H,s,OCH2),6.8(1H,d,ArH)7.1(1H,d,ArH),7.3-7.4(4H,m,4xArH),7.6(2H,m,2xArH)
136 0.3(9H,s,3xSiCH3),0.9(3H,t,CH3),1.5(2H,m,CH2)2.5(2H,m,CH2),4.1(3H,s,OCH3),7.3(1H,m,ArH)7.7(1H,m,ArH),8.3(1H,d,ArH)
148 0.8-1.0(6H,m,2xCH3),1.4-1.9(8H,m,4xCH2),2.5(2H,m,CH2)4.4(2H,m,OCH2),7.1(1H,d,ArH),7.6(1H,dd,ArH),8.3(1H,d,ArH)
186 0.9(3H,t,CH3),1.03(3H,t,CH3),1.53(4H,m,2xCH2)1.82(2H,m,CH2),2.49(2H,t,CH2),4.44(2H,t,CH2)7.39(2H,m,2xArH),7.6(1H,m,ArH),8.22(1H,m,ArH)
171 0.8-1.1(6H,m,2xCH3),1.3-1.5(4H,m,2xCH2),1.7-1.9(2H,m,CH2)2.3(2H,m,CH2),4.4(2H,t,OCH2),6.6(2H,m,ArH)7.4(1H,t,ArH)
172 0.9-1.1(6H,m,2xCH3),1.5-1.65(4H,m,2xCH2)1.8-1.9(2H,m,CH2),2.5(2H,m,CH2),4.4(2H,t,OCH2)5.3(2H,s,OCH2Ph),6.8(1H,d,ArH),6.9(1H,d,ArH)7.3(1H,m,ArH),7.35-7.45(3H,m,3xArH),7.6(2H,m,2xArH)
174 0.9(3H,m,CH3),1.5(2H,m,CH2),1.7(4H,m,2xCH2),1.9(4H,m,2xCH2),2.5(2H,t,CH2),3.9(3H,s,OCH3),5.4(1H,m,OCH),7.1(1H,d,ArH),7.3(1H,dd,ArH),7.6(1H,d,ArH)
175 0.9(3H,t,CH3),1.5(2H,m,CH2),2.5(2H,m,CH2),3.0(6H,s,NMe2)3.9(3H,s,OCH3),7.1(1H,d,ArH),7.3(1H,dd,ArH),7.6(1H,d,ArH)
182 0.95(3H,t,CH3),1.5(4H,m,2xCH2),1.7-1.95(6H,m,3xCH2),2.4(2H,m,CH2),5.35(1H,m,CH),7.26(1H,d,ArH),7.5(1H,dd,ArH),8.16(1H,d,ArH)
159 0.98(3H,t,CH3),1.0(3H,t,CH3),1.54(4H,m,2xCH2),1.8(2H,m,CH2),2.5(2H,t,CH2),4.4(2H,t,CH2),5.32(1H,d,CH),5.83(1H,d,CH),6.78(1H,m,CH),7.32(1H,d,ArH),7.63(1H,dd,ArH),8.2(1H,d,ArH)
190 1.0(3H,t,CH3),1.5-1.6(2H,m,CH2)2.5(2H,m,CH2),2.6(3H,s,SCH3)4.6(2H,m,CH2),5.3-5.5(2H,m,CH2)5.9-6.1(1H,m,CH),6.7(1H,d,ArH)7.0(1H,dd,ArH),8.1(1H,d,ArH)
210 0.85(3H,t,CH3),1.45(2H,m,CH2),235(2H,m,CH2),4.4(2H,d,OCH2),5.2(1H,d,CH),5.3(1H,d,CH),5.92(1H,m,CH),7.0(1H,d,ArH),7.38(1H,dd,ArH),7.58(1H,d,ArH)
220 1.0(6H,t,2xCH3),1.6(4H,m,2xCH2),1.8(2H,m,CH2),2.6(2H,m,CH2),4.1(2H,t,OCH2),7.6(1H,d,ArH),7.8(1H,d,ArH)
221 0.8(3H,t,CH3),1.4-1.5(2H,m,CH2),2.4(2H,m,CH2),3.8(3H,s,OCH3),7.0(1H,d,ArH),7.4(1H,dd,ArH),7.6(1H,d,ArH)
222 1.0(9H,m,3xCH3),1.6-2.0(3H,m,CH2+CH),2.6(4H,m,2xCH2),4.05(2H,t,CH2),7.1(1H,d,ArH),7.6(1H,dd,ArH),7.8(1H,d,ArH)
229 1.0(3H,t,CH3),1.5-2.0(1OH,m,CH2x5),2.6(2H,m,CH2),4.8(1H,bs,OCH),7.2(1H,d,ArH),7.6(1H,dd,ArH),7.8(1H,d,ArH)
232 1.0(3H,t,CH3),1.6(2H,m,CH2),1.7(3H,d,CH3),2.6(2H,m,CH2)4.65(2H,d,CH2),5.8(2H,m,2xCH),7.2(1H,d,ArH),7.58(1H,dd,ArH)7.78(1H,d,ArH)
246 2 异构体0.6(6H,t,2xCH3),0.85(3H,t,CH3),1.0-1.2(11H,m,CH3+4xCH2),3.85(2H,q,OCH2 肟 ),4.0(6H,m,2xOCH2+OCH2 肟),6.25(1H,d,ArH),7.05(1H,d,ArH),7.15(1H,dd,ArH),7.3(1H,d,ArH),7.5(1H,d,ArH),7.7(1H,d,ArH),7.9(1H,s,CH=NOR)8.05(1H,s,CH=NOR)
247 2 isomers0.8(6H,t,2xCH3),1.25(4H,m,2xCH2),1.45(4H,m,2xCH2),4.15(4H,t,2xOCH2),4.5(2H,d,OCH2),4.65(2H,d,OCH2),5.1(2H,m,2xC=CH),5.25(2H,m,2xC=CH),5.75(1H,m,CCH=C),6.0(1H,m,CCH=C),6.45(1H,d,ArH),7.25(1H,d,ArH),7.35(1H,dd,ArH),7.55(1H,d,ArH),7.7(1H,dd,ArH),7.95(1H,d,ArH),8.15(1H,s,CH=NOR),8.3(1H,s,CH=NOR)
257 1.0(6H,m,2xCH3),1.6(4H,m,2xCH2),1.9(2H,m,CH2),2.6(2H,m,CH2)4.15(2H,t,OCH2),7.45(1H,d,ArH),8.35(1H,dd,ArH),8.6(1H,d,ArH)
267 1.05(6H,m,2xCH3),1.3(3H,d,CH3),1.55-1.95(4H,m,2xCH2),2.5(2H,m,CH2),4.4(1H,m,CH),7.2(1H,d,ArH),7.55(1H,dd,ArH),7.8(1H,d,ArH)
283 1.0(6H,m,2xCH3),1.5-1.7(4H,m,2xCH2),1.85(2H,m,CH2),2.55(2H,t,CH2),4.85(3H,s,OCH3),4.05(2H,m,CH2),6.85(2H,m,2ArH),7.55(1H,d,ArH)
310 0.9(3H,t,CH3),1.5(2H,m,CH2),2.4(2H,m,CH2),5.2(2H,s,OCH2),6.9(1H,d,ArH),7.1(1H,d,ArH),7.4-7.5(6H,bs,ArH),9.7(1H,bs,OH)
315 0.9(3H,t,CH3),1.2(9H,t,3xCH3),1.5(2H,m,CH2),2.4(2H,m,CH2),3.0(6H,q,3xCH2),7.0(1H,d,ArH),7.4(1H,dd,ArH),8.0(1H,d,ArH)
317 1.02(3H,t,CH3),1.6(2H,m,CH2),1.9(2H,m,CH2),2.43(3H,s,Ar CH3),4.1(2H,t,OCH2),5.6(1H,m,CH),6.4(1H,m,CH),6.8(1H,m,CH),7.2(1H,m,ArH),7.3(1H,dd,ArH),7.5(1H,d,ArH)
199c 1.9(3H,t,CH3),1.3(6H,d,2xCH3),1.5(6H,d,2xCH3),1.6(2H,m,CH2),2.4(2H,m,CH2),4.1(1H,m,CH),4.3(2H,t,CH2),4.5-4.8(3H,m,3xCH),5.5(1H,d,CH),7.3(1H,d,ArH),7.5(1H,dd,ArH),8.1(1H.d,ArH)
199g 1.0(3H,t,CH3),1.4-1.65(8H,m,4xCH2),1.7-1.9(2H,m,CH2),1.95-2.05(2H,m,CH2),2.5(2H,m,CH2),2.6(3H,s,SCH3),4.3-4.4(1H,m,OCH),6.8(1H,d,ArH),6.9(1H,dd,ArH),8.1(1H,d,ArH)
试验实例
这些化合物对以下一种或多种真菌的活性已作了评价:
蕃茄晚疫病
葡萄霜霉病
大麦白粉病
小麦白粉病
水稻稻瘟病
灰霉病
苹果黑星病
颖枯病
水稻纹枯病
这些化合物配成所需浓度的水溶液或含有湿润剂的分散液,通过喷雾或浸润试验植物的茎底部而施用,然后在植株或植株的部分接种上适当的试验病原菌,并保持适宜于植物生长的病害发展的防治环境条件下。经过一段适当的时间之后,对植物侵染部分的侵染程度进行目测。这些化合物的活性评价分为1-3级。1为低效或无效,2为中等防治,3为防治好至完全防治。在500ppm(重量/体积)或低于此浓度情况下,以下化合物对特定的真菌具有2级或更高的防治效果:蕃茄晚疫病:75,201葡萄霜霉病:12,24a,42,47,49,65,75-6,82,92,107,118-20,146-9,158,202,204-5,213,217-8,241-2,247,252,318。大麦白粉病:12,14,41,42,44-5,49-50,201-2,205-5。小麦白粉病:2,5,6,11,23,26a,44-5,47,49-54,56-59,61-64,66-69,71,74-5,77-9,82,84-5,87-95,97,101,107,109,111,113-4,116,119,122,124,129,136,138,143,145,148-9,151-2,155-62,216-8,221-2,232,236,239,241,250,256,258-9,261,265-9,271-2,278-9,283,289-290,306,316。稻瘟病:56,69,71,73,79,86,106,114,251,316灰霉病:50,87,109,112,123,213,222,227,229,241,250,306。苹果黑星病:78,205,208,217,226,237,259。颖枯病:43,90,117,129,202,232,272,296水稻纹枯病:14,88,202
Claims (4)
其中,
Z和Y之一是CO,另一个是C-W-R2,虚线表示为了满足价键需要时存在的双键,
W是O,S(O)n,N(R3),N(R3)N(R4),N(R3)O,或ON(R3);
R1是氢,或可任意选择取代的烷基,烯基,炔基,环烷基,苯基或杂环基;
R2,R3和R4可以是相同的,也可以是不相同的,其含义同R1,或是酰基,或是R2和R3,或R2和R4,或R3和R4与连接它们的氮或氧一起形成可任意选择取代的环,该环可以含有其它杂原子;
每个X可以是相同的,也可以是不相同的,它们是卤素,CN,NO2,SF5,B(OH)2,三烷基硅烷基,或是E,OE或S(O)nE,其中E是含义如R2的基团,或是可任意选择取代的氨基;或是两个邻近的X与连接它们的其它原子一起形成可任意选择取代的碳环或杂环;
n是0,1或2;和
p是0至4,
附带条件:
a)当W是0时,R2不能是邻位取代的苄基,和
b)当p是0时,R1不能是氢。
2.式Ⅰ的化合物,
式中,
Z和Y之一是CO,另一个是C-W-R2,虚线表示为了满足价键需要时存在的双键,
W是O,S(O)n,N(R3),N(R3)N(R4),N(R3)O,或ON(R3);
R1是可任意选择取代的烷基,烯基,炔基,环烷基或苯基;
R2,R3和R4可以是相同的,也可以是不相同的,其含义同R1,或是酰基,或是可任意选择取代的杂环,或是R2和R3,或R2和R4,或R3和R4与连接它们的氮或氧一起形成可任意选择取代的环,该环可以含有其它杂原子;
每个X可以是相同的,也可以是不相同的,它们是卤素,CN,NO2,SF5,B(OH)2,三烷基硅烷基或是E,OE或S(O)nE,其中E的含义如R2,或是可任意选择取代的氨基;或是两个邻近的X和连接它们的其它原子一起形成可任意选择取代的碳环或杂环;
n是0,1或2;和
p是1或2,一个X基是在6-位的。
附带条件:
a)当Z是CO和WR2是甲氧基时,R1不是1-甲基苄基或1,1-二甲基烯丙基,
b)当Z是CO和WR2是N(CH3)2时,两个X基团不能形成在5、6位稠合的苯并环,和
c)当Y是CO时,W-R2不是甲氧基。
3.一种杀菌组合物,其组成包括一种权利要求1或2要求的式Ⅰ化合物和农业上可接受的稀释剂或载体。
4.在侵染地点或易被侵染的地点防治病源真菌的方法,该方法包括向该地点施用权利要求1或2的通式(Ⅰ)化合物。
Applications Claiming Priority (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9521023.3 | 1995-10-13 | ||
GBGB9521023.3A GB9521023D0 (en) | 1995-10-13 | 1995-10-13 | Fungicides |
GBGB9524152.7A GB9524152D0 (en) | 1995-11-25 | 1995-11-25 | Fungicides |
GB9524152.7 | 1995-11-25 | ||
GB9525525.3 | 1995-12-14 | ||
GBGB9525526.1A GB9525526D0 (en) | 1995-12-14 | 1995-12-14 | Fungicides |
GBGB9525525.3A GB9525525D0 (en) | 1995-12-14 | 1995-12-14 | Fungicides |
GB9525514.7 | 1995-12-14 | ||
GB9525524.6 | 1995-12-14 | ||
GBGB9525524.6A GB9525524D0 (en) | 1995-12-14 | 1995-12-14 | Fungicides |
GBGB9525514.7A GB9525514D0 (en) | 1995-12-14 | 1995-12-14 | Fungicides |
GB9525526.1 | 1995-12-14 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1204330A true CN1204330A (zh) | 1999-01-06 |
CN1117741C CN1117741C (zh) | 2003-08-13 |
Family
ID=27547250
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96198881A Expired - Fee Related CN1117741C (zh) | 1995-10-13 | 1996-10-11 | 杂环杀菌剂 |
Country Status (19)
Country | Link |
---|---|
US (1) | US6034121A (zh) |
EP (1) | EP0861242B1 (zh) |
JP (1) | JP2000500739A (zh) |
KR (1) | KR100428274B1 (zh) |
CN (1) | CN1117741C (zh) |
AT (1) | ATE201674T1 (zh) |
AU (1) | AU7223896A (zh) |
BR (1) | BR9610970A (zh) |
CA (1) | CA2233666C (zh) |
DE (1) | DE69613139T2 (zh) |
DK (1) | DK0861242T3 (zh) |
ES (1) | ES2157462T3 (zh) |
GR (1) | GR3036017T3 (zh) |
HU (1) | HUP9900753A3 (zh) |
IL (1) | IL123701A (zh) |
PL (1) | PL187175B1 (zh) |
PT (1) | PT861242E (zh) |
TW (1) | TW420671B (zh) |
WO (1) | WO1997013762A1 (zh) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101456853B (zh) * | 2009-01-05 | 2011-09-21 | 江苏省农业科学院 | 仿生系列化合物7-取代-8-(3,3’-二取代丙基)苯并吡喃-2-酮类合成及其作为农药的应用 |
CN103524471A (zh) * | 2013-10-31 | 2014-01-22 | 青岛农业大学 | 一种n-烷(酰)基取代的氨基香豆素及其杀虫活性 |
CN106900712A (zh) * | 2016-12-05 | 2017-06-30 | 青岛农业大学 | N‑硬脂酰基‑6‑氨基香豆素的制剂及其应用 |
CN109053660A (zh) * | 2018-07-13 | 2018-12-21 | 青岛农业大学 | 含三氟甲硫基香豆素类化合物、其合成方法及其应用 |
CN109134444A (zh) * | 2018-02-11 | 2019-01-04 | 陕西师范大学 | 3-(2-呋喃)-4-羟基香豆素类化合物及其制备方法和抗植物真菌的应用 |
CN112939919A (zh) * | 2021-03-11 | 2021-06-11 | 西华大学 | 2-氨基苯并吡喃类化合物及其在农药中的应用 |
CN113004240A (zh) * | 2021-03-11 | 2021-06-22 | 西华大学 | 苯并吡喃类化合物及其在农药中的用途 |
CN113024500A (zh) * | 2021-03-11 | 2021-06-25 | 西华大学 | 6,8-二溴苯并吡喃衍生物及其在农药中的应用 |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998027080A1 (en) * | 1996-12-19 | 1998-06-25 | Agrevo Uk Limited | Chromones useful as fungicides |
AU4694999A (en) * | 1998-08-06 | 2000-02-28 | Warner-Lambert Company | Use of thiazolidinedione derivatives for the treatment or prevention of cataracts |
US6169185B1 (en) | 1999-02-25 | 2001-01-02 | Day-Glo Color Corp. | Ink jet printing inks |
DE19935963A1 (de) * | 1999-07-30 | 2001-02-01 | Bayer Ag | Biphenylsubstituierte cyclische Ketoenole |
EP1416799A4 (en) * | 2001-07-23 | 2004-11-10 | Univ Ramot | METHODS AND COMPOSITIONS FOR TREATING FUNGAL INFECTIONS |
FR2828196A1 (fr) * | 2001-08-03 | 2003-02-07 | Aventis Cropscience Sa | Derives de chromone a action fongicide, procede de preparation et application dans le domaine de l'agriculture |
US7148253B2 (en) * | 2002-05-14 | 2006-12-12 | Xtl Biopharmaceuticals Ltd. | 4-thio coumarins |
AU2003241429A1 (en) * | 2002-05-14 | 2003-12-02 | Vivoquest, Inc. | 4-thio coumarins |
MXPA05001785A (es) * | 2002-08-13 | 2005-04-25 | Warner Lambert Co | Derivados de cromona como inhibidores de las metaloproteinasas de matriz. |
EP1443044A1 (fr) * | 2003-02-03 | 2004-08-04 | Bayer CropScience SA | Procédés de préparation de dérivés de iodo-chromones fongicides |
CN1281599C (zh) * | 2003-05-15 | 2006-10-25 | 中国科学院上海有机化学研究所 | 香豆素类化合物和合成方法 |
US7538233B2 (en) * | 2003-09-05 | 2009-05-26 | Aventis Pharmaceuticals Inc. | Coumarins as iNOS inhibitors |
CN1310899C (zh) * | 2003-11-11 | 2007-04-18 | 沈阳化工研究院 | 具有杀虫、杀菌活性的苯并吡喃酮类化合物及制备与应用 |
EP1614685A1 (en) * | 2004-07-07 | 2006-01-11 | Bayer CropScience AG | Process for preparing 2-chloro-6-Halogeno-3-alkyl-4H-chrom en-4-one or 2-chloro-3-alkyl-4H-chromen-4-one derivatives |
JP4561245B2 (ja) * | 2004-08-31 | 2010-10-13 | 住友化学株式会社 | クロモン化合物及びその用途 |
BRPI0515261A (pt) * | 2004-09-30 | 2008-07-15 | Neurosearch As | composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, uso do composto quìmico ou de qualquer um de seus isÈmeros ou de qualquer mistura de seus isÈmeros, ou um sal farmaceuticamente aceitável do mesmo, e, método para o tratamento, a prevenção ou o alìvio de uma doença ou de um distúrbio ou de uma condição de um corpo de animal vivo |
MX2007002384A (es) * | 2004-09-30 | 2007-05-11 | Neurosearch As | Nuevos derivados de cromen-2-ona y su uso como inhibidores de la reabsorcion del neurotransmisor de monoamina. |
US7617092B2 (en) * | 2004-12-01 | 2009-11-10 | Microsoft Corporation | Safe, secure resource editing for application localization |
WO2006066756A1 (en) * | 2004-12-21 | 2006-06-29 | F. Hoffmann-La Roche Ag | Chroman derivatives and uses thereof in the treatment of cns disorders |
AU2006343604A1 (en) * | 2006-05-15 | 2007-11-22 | Xtl Biopharmaceuticals, Ltd. | 3,4-disubstituted coumarin and quinolone compounds |
MX2009000148A (es) * | 2006-07-07 | 2009-10-26 | Kalypsys Inc | Inhibidores heteroaril biciclicos de fosfodiesterasa 4. |
EP2121677B1 (en) | 2006-12-20 | 2010-11-03 | NeuroSearch A/S | Novel chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
TW200904815A (en) * | 2007-05-09 | 2009-02-01 | Neurosearch As | Novel compounds |
JP2012526744A (ja) | 2009-05-15 | 2012-11-01 | ノイロサーチ アクティーゼルスカブ | クロメン−2−オン誘導体及びモノアミン神経伝達物質再取り込み阻害剤としてのそれらの使用 |
WO2011092061A1 (en) | 2010-01-29 | 2011-08-04 | Neurosearch A/S | Chromen-2-one derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
US8318953B2 (en) * | 2010-06-23 | 2012-11-27 | Aat Bioquest, Inc. | Reactive coumarin derivatives and their use in cellular analyses |
US20130079394A1 (en) * | 2011-09-23 | 2013-03-28 | Cnrs (Centre National Recherche Scientifique) | Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods |
US8933239B1 (en) | 2013-07-16 | 2015-01-13 | Dow Global Technologies Llc | Bis(aryl)acetal compounds |
US9410016B2 (en) | 2013-07-16 | 2016-08-09 | Dow Global Technologies Llc | Aromatic polyacetals and articles comprising them |
US9063420B2 (en) | 2013-07-16 | 2015-06-23 | Rohm And Haas Electronic Materials Llc | Photoresist composition, coated substrate, and method of forming electronic device |
US8962779B2 (en) | 2013-07-16 | 2015-02-24 | Dow Global Technologies Llc | Method of forming polyaryl polymers |
WO2017115333A1 (en) * | 2015-12-30 | 2017-07-06 | Investigaciones Biológicas En Agroquímicos Rosario S.A. | Herbicidal composition comprising chromone derivatives and a method for weed control |
CN107556296B (zh) * | 2017-09-06 | 2020-10-02 | 南京工业大学 | 一种2-羟基-3-氮杂环色酮类化合物及其合成方法和在抗真菌药物中的应用 |
EP4015512A1 (en) | 2020-12-16 | 2022-06-22 | AMO Ireland | Optically active devices |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1225658B (de) * | 1960-11-15 | 1966-09-29 | Geigy Ag J R | Verfahren zur Herstellung von Cumarinderivaten |
US3141893A (en) * | 1960-11-15 | 1964-07-21 | Geigy Chem Corp | 4-amino-coumarins |
FR2321M (fr) * | 1962-01-16 | 1964-02-10 | Lipha | Nouveaux médicaments cholérétiques de la série des hydroxy-coumarines. |
CA978977A (en) * | 1971-05-31 | 1975-12-02 | Yasuo Makisumi | Coumarin derivatives and production thereof |
US4065574A (en) * | 1975-08-29 | 1977-12-27 | The Upjohn Company | New method for controlling fungi using 4-chromone, 4-chromanone, 4-chromone oxime and 4-chromanone oxime compounds |
FR2368952A1 (fr) * | 1976-02-25 | 1978-05-26 | Lipha | Nouveaux aminoalcoxy-4 (2 h) pyranone-2,3 substitues-5,6 condenses |
ZA873745B (en) * | 1986-06-04 | 1988-10-26 | Daiichi Seiyaku Co | Benzopyran derivatives |
AU8612491A (en) * | 1990-09-07 | 1992-03-30 | Schering Corporation | Antiviral compounds |
DE69128481T2 (de) * | 1990-09-07 | 1998-04-09 | Schering Corp | Antivirale und antihypertensive verbindungen |
JPH05331009A (ja) * | 1992-06-01 | 1993-12-14 | Asahi Denka Kogyo Kk | 水中有害生物防除剤 |
US5510375A (en) * | 1993-11-19 | 1996-04-23 | Warner-Lambert Company | Coumarin derivatives as protease inhibitors and antiviral agents |
US5563280A (en) * | 1994-07-25 | 1996-10-08 | American Cyanamid Co. | 4-Phenoxycoumarins as herbicidal agents |
-
1996
- 1996-10-11 IL IL12370196A patent/IL123701A/en not_active IP Right Cessation
- 1996-10-11 BR BR9610970A patent/BR9610970A/pt not_active Application Discontinuation
- 1996-10-11 WO PCT/GB1996/002491 patent/WO1997013762A1/en active IP Right Grant
- 1996-10-11 KR KR10-1998-0702689A patent/KR100428274B1/ko not_active IP Right Cessation
- 1996-10-11 PT PT96933541T patent/PT861242E/pt unknown
- 1996-10-11 CN CN96198881A patent/CN1117741C/zh not_active Expired - Fee Related
- 1996-10-11 DK DK96933541T patent/DK0861242T3/da active
- 1996-10-11 PL PL96326159A patent/PL187175B1/pl not_active IP Right Cessation
- 1996-10-11 ES ES96933541T patent/ES2157462T3/es not_active Expired - Lifetime
- 1996-10-11 AT AT96933541T patent/ATE201674T1/de not_active IP Right Cessation
- 1996-10-11 EP EP96933541A patent/EP0861242B1/en not_active Expired - Lifetime
- 1996-10-11 AU AU72238/96A patent/AU7223896A/en not_active Abandoned
- 1996-10-11 CA CA002233666A patent/CA2233666C/en not_active Expired - Fee Related
- 1996-10-11 DE DE69613139T patent/DE69613139T2/de not_active Expired - Fee Related
- 1996-10-11 JP JP9514831A patent/JP2000500739A/ja not_active Ceased
- 1996-10-11 HU HU9900753A patent/HUP9900753A3/hu unknown
- 1996-10-17 TW TW085112706A patent/TW420671B/zh not_active IP Right Cessation
-
1998
- 1998-04-01 US US09/051,135 patent/US6034121A/en not_active Expired - Fee Related
-
2001
- 2001-06-13 GR GR20010400495T patent/GR3036017T3/el not_active IP Right Cessation
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101456853B (zh) * | 2009-01-05 | 2011-09-21 | 江苏省农业科学院 | 仿生系列化合物7-取代-8-(3,3’-二取代丙基)苯并吡喃-2-酮类合成及其作为农药的应用 |
CN103524471A (zh) * | 2013-10-31 | 2014-01-22 | 青岛农业大学 | 一种n-烷(酰)基取代的氨基香豆素及其杀虫活性 |
CN106900712A (zh) * | 2016-12-05 | 2017-06-30 | 青岛农业大学 | N‑硬脂酰基‑6‑氨基香豆素的制剂及其应用 |
CN109134444A (zh) * | 2018-02-11 | 2019-01-04 | 陕西师范大学 | 3-(2-呋喃)-4-羟基香豆素类化合物及其制备方法和抗植物真菌的应用 |
CN109053660A (zh) * | 2018-07-13 | 2018-12-21 | 青岛农业大学 | 含三氟甲硫基香豆素类化合物、其合成方法及其应用 |
CN109053660B (zh) * | 2018-07-13 | 2022-04-26 | 青岛农业大学 | 含三氟甲硫基香豆素类化合物、其合成方法及其应用 |
CN112939919A (zh) * | 2021-03-11 | 2021-06-11 | 西华大学 | 2-氨基苯并吡喃类化合物及其在农药中的应用 |
CN113004240A (zh) * | 2021-03-11 | 2021-06-22 | 西华大学 | 苯并吡喃类化合物及其在农药中的用途 |
CN113024500A (zh) * | 2021-03-11 | 2021-06-25 | 西华大学 | 6,8-二溴苯并吡喃衍生物及其在农药中的应用 |
CN113024500B (zh) * | 2021-03-11 | 2023-02-03 | 西华大学 | 6,8-二溴苯并吡喃衍生物及其在农药中的应用 |
CN112939919B (zh) * | 2021-03-11 | 2023-02-03 | 西华大学 | 2-氨基苯并吡喃类化合物及其在农药中的应用 |
CN113004240B (zh) * | 2021-03-11 | 2023-02-03 | 西华大学 | 苯并吡喃类化合物及其在农药中的用途 |
Also Published As
Publication number | Publication date |
---|---|
IL123701A (en) | 2002-03-10 |
IL123701A0 (en) | 1998-10-30 |
WO1997013762A1 (en) | 1997-04-17 |
DE69613139T2 (de) | 2001-09-13 |
ES2157462T3 (es) | 2001-08-16 |
CA2233666A1 (en) | 1997-04-17 |
KR19990064203A (ko) | 1999-07-26 |
MX9802858A (es) | 1998-11-30 |
HUP9900753A3 (en) | 2000-04-28 |
TW420671B (en) | 2001-02-01 |
EP0861242A1 (en) | 1998-09-02 |
US6034121A (en) | 2000-03-07 |
DK0861242T3 (da) | 2001-08-06 |
AU7223896A (en) | 1997-04-30 |
PL326159A1 (en) | 1998-08-31 |
PL187175B1 (pl) | 2004-05-31 |
CN1117741C (zh) | 2003-08-13 |
ATE201674T1 (de) | 2001-06-15 |
CA2233666C (en) | 2006-05-09 |
GR3036017T3 (en) | 2001-09-28 |
JP2000500739A (ja) | 2000-01-25 |
BR9610970A (pt) | 1999-04-06 |
PT861242E (pt) | 2001-10-30 |
EP0861242B1 (en) | 2001-05-30 |
DE69613139D1 (de) | 2001-07-05 |
HUP9900753A2 (hu) | 1999-07-28 |
KR100428274B1 (ko) | 2005-01-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1117741C (zh) | 杂环杀菌剂 | |
CN1050355C (zh) | 稠合双环嘧啶酮类化合物、含有它们的杀真菌组合物及其应用 | |
CN1147456C (zh) | 杀真菌的2-甲氧基二苯甲酮类化合物 | |
CN1255380C (zh) | 吡咯酰胺和吡咯硫代酰胺杀菌剂 | |
CN1025649C (zh) | 杀真菌组合物 | |
CN1044369C (zh) | 吡啶甲酸及除草组合物 | |
CN1020901C (zh) | 杀真菌剂组合物其制备方法及用途 | |
CN1019260B (zh) | 含喹唑啉衍生物的杀真菌剂 | |
CN1255043A (zh) | 杀真菌剂 | |
CN1279027C (zh) | 杀真菌的5-苯基取代的2-(氰氨基)嘧啶化合物 | |
CN1131947A (zh) | 吡唑衍生物 | |
CN1147193A (zh) | 杀虫剂n-(取代芳甲基)-4-[双(取代苯基)哌啶 | |
CN1027125C (zh) | 杀真菌剂的组合物 | |
CN1081674A (zh) | 杀菌剂1,2,4-三唑化合物 | |
CN1063101A (zh) | 哌啶衍生物 | |
CN1036571A (zh) | 苯并恶嗪酮化合物和含有这种化合物的除草组合物 | |
CN1051556A (zh) | 嘧啶衍生物及其制备和应用 | |
CN1452458A (zh) | 除草的5-苄氧基甲基-1,2-异噁唑啉衍生物 | |
CN1040437C (zh) | 除草的喹啉基噁二唑衍生物,它们的制备方法和含有它们的除草组合物 | |
CN1274697C (zh) | 具有杀菌除草活性的取代苯氧乙酰氧基芳杂环基烃基膦酸酯盐及制备 | |
CN86101080A (zh) | 咪唑衍生物的制备方法和作为杀菌剂的应用 | |
CN1199640C (zh) | 1,2,4-三嗪-3-酮,其衍生物取代的4,5-二氢-1,2,4-三嗪-3-酮,以及它们作为杀菌剂和杀虫剂的用途 | |
CN1095067A (zh) | 噁(噻)-二唑-氧-苯基丙烯酸酯类 | |
CN1043888C (zh) | 杀真菌和除草三唑 | |
CN1268206C (zh) | 用作杀真菌剂的噻唑并[4,5-b]吡啶 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |