CN1249752A - 用作杀微生物剂的稠合的唑类衍生物 - Google Patents
用作杀微生物剂的稠合的唑类衍生物 Download PDFInfo
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- CN1249752A CN1249752A CN98803033A CN98803033A CN1249752A CN 1249752 A CN1249752 A CN 1249752A CN 98803033 A CN98803033 A CN 98803033A CN 98803033 A CN98803033 A CN 98803033A CN 1249752 A CN1249752 A CN 1249752A
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- 239000002855 microbicide agent Substances 0.000 title claims abstract description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 claims abstract description 44
- 239000002253 acid Substances 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 150000007980 azole derivatives Chemical class 0.000 claims abstract description 22
- -1 thiocarbamoyl Chemical group 0.000 claims description 130
- 229910052799 carbon Inorganic materials 0.000 claims description 102
- 239000002585 base Substances 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 239000001301 oxygen Substances 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 239000005864 Sulphur Substances 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 150000001345 alkine derivatives Chemical class 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 230000003641 microbiacidal effect Effects 0.000 claims description 6
- JYLLSRXJCBEPFX-UHFFFAOYSA-N 1h-imidazole-2-carbothioamide Chemical class NC(=S)C1=NC=CN1 JYLLSRXJCBEPFX-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 230000002152 alkylating effect Effects 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 4
- 229940124561 microbicide Drugs 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000005108 alkenylthio group Chemical group 0.000 claims description 3
- 244000005700 microbiome Species 0.000 claims description 3
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 8
- 229910052751 metal Chemical class 0.000 abstract description 2
- 239000002184 metal Chemical class 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 101
- 125000005843 halogen group Chemical group 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000011737 fluorine Substances 0.000 description 18
- 229910052731 fluorine Inorganic materials 0.000 description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000003851 azoles Chemical class 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 241000589516 Pseudomonas Species 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000012973 diazabicyclooctane Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- AGEBJYJJWHBPJT-UHFFFAOYSA-N $l^{1}-oxidanylsulfonylmethane Chemical compound CS([O])(=O)=O AGEBJYJJWHBPJT-UHFFFAOYSA-N 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 241000228452 Venturia inaequalis Species 0.000 description 4
- 235000009754 Vitis X bourquina Nutrition 0.000 description 4
- 235000012333 Vitis X labruscana Nutrition 0.000 description 4
- 240000006365 Vitis vinifera Species 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 4
- 150000005826 halohydrocarbons Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 4
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- 229940031815 mycocide Drugs 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000005946 Cypermethrin Substances 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical class CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 241001223281 Peronospora Species 0.000 description 3
- 241000233614 Phytophthora Species 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 241000228453 Pyrenophora Species 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 241000722133 Tilletia Species 0.000 description 3
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004176 ammonification Methods 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 150000003868 ammonium compounds Chemical class 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
Abstract
本发明公开了式(Ⅰ)的新的稠合的唑类衍生物,其中R1,R2,A和G具有说明书中给出的定义,以及其酸加成盐和金属盐配合物,制备它们的几种方法,以及它们作为植物保护和材料保护中杀微生物剂的用途。
Description
本发明涉及新的稠合的唑类衍生物,其多种制备方法,以及其作为农作物保护和材料保护中的杀微生物剂的用途。
一些稠合的唑类衍生物具有杀真菌性能(参见DE-A19523446)。例如1-(3,5-二甲基异噁唑-4-磺酰基)-1H-苯并三唑可以用来防治真菌。该物质活性好,但是在某些情况下以低施用比例时不令人满意。
因此,本发明提供下式新的稠合的唑类衍生物以及它们的酸加成盐和金属盐配合物,其中R1和R2与它们所连接的碳原子一起代表任选被取代的杂环或者代表任选被取代的苯稠合的杂环,G代表氮或者基团其中R3 代表氢,卤素,氰基,硝基,三氟甲基,硫代氨基甲酰基,氰硫基或者基团其中R4代表烷基,A代表下面基团之一
-SO2-R5,
其中Y代表氧或硫,R5代表任选被取代的不饱和的杂环基团,R6和R7各自独立地代表烷基,卤代烷基,烷氧基,卤代烷氧基,烷硫基,卤代烷硫基,链烯基,卤代链烯基,链烯基氧基,链烯基硫基,炔烃基,炔烃基氧基,炔烃基硫基,任选被烷基-、环烷基-或芳基-取代的氨基,任选被取代的芳基,任选被取代的芳基氧基,任选被取代的芳基硫基,任选被取代的环烷基,任选被取代的环烷基氧基,任选被取代的环烷基硫基或者代表任选被取代的饱和的或不饱和的杂环基团,或者R6和R7与它们所连接的磷原子一起代表任选被取代的杂环基团。
在这些定义中,饱和的或不饱和的烃链,例如烷基,链烯基或炔烃基,在各种情况下是直链或支链的,包括与杂原子结合的情况,例如在烷氧基,烷硫基或烷基氨基中。
此外,发现进行下面的反应时得到了式(I)的稠合的唑类衍生物以及它们的酸加成盐和金属盐配合物:
A-X1 (III)其中A如上定义,和X1代表卤素,或者
R4-X2 (IV)其中R4如上定义,和X2代表离去基团,如果适当,向得到的式(I)的化合物中加入酸或金属盐。
最后发现,式(I)的稠合的唑类衍生物以及它们的酸加成盐和金属盐配合物具有非常好的杀微生物性能,可以用于农作物保护和材料保护中。
令人惊奇地,本发明物质具有比1-(3,5-二甲基异噁唑-4-磺酰基)-1H-苯并三唑更好的杀真菌活性,1-(3,5-二甲基异噁唑-4-磺酰基)-1H-苯并三唑是先前技术中具有相似结构和相同作用方向的活性化合物。
式(I)提供了本发明物质的一般定义。
R1和R2与它们所连接的碳原子一起优选代表含有一个、两个或三个相同或不同的例如氧、硫和/或氮的杂原子,并且可以被相同或不同的选自下组的取代基一至三取代的5-或6-元杂环:
卤素,氰基,硝基,羟基,氨基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,具有1-4个碳原子的烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷氧基,烷氧基部分中具有1-4个碳原子的烷氧羰基,具有3-6个碳原子的环烷基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基亚磺酰基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基磺酰基,具有1-4个碳原子的烷基氨基,具有1-4个碳原子的羟基烷基氨基,各烷基中具有1-4个碳原子的二烷基氨基,在烷基部分中具有1-4个碳原子的烷基羰基,在烷基部分中具有1-4个碳原子的肟基烷基,在烷氧基部分中具有1-4个碳原子和在烷基部分中具有1-4个碳原子的烷氧基亚氨基烷基,在烷基部分中具有1-4个碳原子的烷基羰基氧基和在卤代烷基中具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基羰基氧基,或者R1和R2与它们所连接的碳原子一起优选代表含有一个或两个相同或不同的例如氧,硫和/或氮的杂原子,并且可以被相同或不同的选自下组的取代基一至三取代的苯稠合的5-或6-元杂环:
卤素,氰基,硝基,羟基,氨基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,具有1-4个碳原子的烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷氧基,烷氧基部分中具有1-4个碳原子的烷氧羰基,具有3-6个碳原子的环烷基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基亚磺酰基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基磺酰基,具有1-4个碳原子的烷基氨基,具有1-4个碳原子的羟基烷基氨基,各烷基中具有1-4个碳原子的二烷基氨基,在烷基部分中具有1-4个碳原子的烷基羰基,在烷基部分中具有1-4个碳原子的肟基烷基,在烷氧基部分中具有1-4个碳原子和在烷基部分中具有1-4个碳原子的烷氧基亚氨基烷基,在烷基部分中具有1-4个碳原子的烷基羰基氧基和在卤代烷基中具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基羰基氧基,
其中,如果杂环或苯稠合杂环含有多于一个的氧原子,则氧原子是不邻接的。
-SO2-R5,其中Y也优选代表氧或硫,R5优选代表含有5或6个成环原子和1-3个相同或不同的例如氧,硫和/或氮的杂原子,并且可以被相同或不同的选自下组的取代基一或二取代的不饱和的杂环基团:卤素,氰基,硝基,羟基,氨基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,具有1-4个碳原子的烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷氧基,烷氧基部分中具有1-4个碳原子的烷氧羰基,具有3-6个碳原子的环烷基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基亚磺酰基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基磺酰基,具有1-4个碳原子的烷基氨基,具有1-4个碳原子的羟基烷基氨基,各烷基中具有1-4个碳原子的二烷基氨基,在烷基部分中具有1-4个碳原子的烷基羰基,在烷基部分中具有1-4个碳原子的肟基烷基,在烷氧基部分中具有1-4个碳原子和在烷基部分中具有1-4个碳原子的烷氧基亚氨基烷基,在烷基部分中具有1-4个碳原子的烷基羰基氧基和在卤代烷基中具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基羰基氧基,R6和R7各自独立地优选代表直链或支链的具有1-4个碳原子的烷基,直链或支链的具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基,直链或支链的具有1-4个碳原子的烷氧基,直链或支链的具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷氧基,直链或支链的具有1-4个碳原子的烷硫基,直链或支链的具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷硫基,直链或支链的具有2-4个碳原子的链烯基,直链或支链的具有2-4个碳原子和1-5个相同或不同的卤原子的卤代链烯基,直链或支链的具有2-4个碳原子的链烯基氧基,直链或支链的具有2-4个碳原子的链烯基硫基,直链或支链的具有2-4个碳原子的炔烃基,直链或支链的具有2-4个碳原子的炔烃基氧基,直链或支链的具有2-4个碳原子的炔烃基硫基,任选被相同或不同的选自具有1-4个碳原子的烷基,具有3-7个碳原子的环烷基和苯基的取代基一或二取代的氨基,或者代表苯基,苯氧基,苯基氨基或苯基硫基,其中这些基团的每一个可以被相同或不同的选自下面的取代基一至三取代:氟,氯,溴,具有1-4个碳原子的烷基,具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷基,具有1-4个碳原子的烷氧基和具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基,或者代表具有3-7个碳原子的环烷基,具有3-7个碳原子的环烷基氧基,具有3-7个碳原子的环烷基硫基,具有3-7个碳原子的环烷基氨基,吡咯烷基,哌啶基或吗啉基,其中每一个上述基团可以被相同或不同的选自氟,氯,溴,具有1-4个碳原子的烷基和具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷基的取代基一至三取代,或者代表含有5或6个成环原子和1-3个相同或不同的例如氧,硫和/或氮的杂原子,并且其每一个可以被相同或不同的选自下组的取代基一或二取代的饱和的或不饱和的杂环基团:卤素,氰基,硝基,羟基,氨基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,具有1-4个碳原子的烷基,具有1-4个碳原子的烷氧基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷氧基,烷氧基部分中具有1-4个碳原子的烷氧羰基,具有3-6个碳原子的环烷基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基亚磺酰基,具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基磺酰基,具有1-4个碳原子的烷基氨基,具有1-4个碳原子的羟基烷基氨基,各烷基中具有1-4个碳原子的二烷基氨基,在烷基部分中具有1-4个碳原子的烷基羰基,在烷基部分中具有1-4个碳原子的肟基烷基,在烷氧基部分中具有1-4个碳原子和在烷基部分中具有1-4个碳原子的烷氧基亚氨基烷基,在烷基部分中具有1-4个碳原子的烷基羰基氧基和在卤代烷基中具有1-4个碳原子和1-5个相同或不同的卤原子的卤代烷基羰基氧基,此外,R6和R7与它们所连接的磷原子一起优选代表含有一个或两个其它相同或不同的杂原子例如氧,硫和/或氮,并且可以被相同或不同的选自氟,氯,溴,具有1-4个碳原子的烷基,具有1-4个碳原子的烷氧基和具有1-4个碳原子和1-5个氟、氯和/或溴的卤代烷氧基的取代基一至三取代的5-或6-元杂环基团。R1和R2与它们所连接的碳原子一起特别代表呋喃二基,噻吩二基,吡咯二基,噁唑二基,噻唑二基,咪唑二基,异噁唑二基,异噻唑二基,吡唑二基,1,2,3-噁二唑二基,1,2,3-噻二唑二基,1,2,3-三唑二基,吡啶二基,哒嗪二基,吡嗪二基,嘧啶二基,1,2,4-三嗪二基,吲哚-2,3-二基,苯并呋喃-2,3-二基,苯并噻吩-2,3-二基,喹啉-2,3-二基,喹唑啉-2,3-二基,苯并[1,4]二噁英(dioxin)-2,3-二基,苯并[1,4]二噻英(dithiin)-2,3-二基,4H-苯并[1,4]噁嗪-2,3-二基,4H-苯并[1,4]噻嗪-2,3-二基,其中这些基团可以被相同或不同的选自下面的基团一或二取代:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,乙基磺酰基,三氟甲基,二氟甲氧基,三氟甲氧基,二氟甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基和乙氧基亚氨基乙基,或者R1和R2一起代表下式基团: 其中这些基团的每一个可以被甲基一或二取代。G还特别代表氮或者基团R3还特别代表氢,氟,氯,溴,碘,氰基,硝基,三氟甲基,硫代氨基甲酰基,氰硫基或者基团R4特别代表甲基或乙基。A还特别代表下面基团之一:
-SO2-R5,Y也特别代表氧或硫。R5特别代表吡咯基,呋喃基,吡唑基,咪唑基,噻唑基,异噻唑基,噁唑基,异噁唑基,噁二唑基,噻二唑基,1,2,3-三嗪基,1,2,4-三嗪基,1,3,5-三嗪基,吡啶基,嘧啶基,吡嗪基或哒嗪基,这些基团的每一个可以被相同或不同的选自下面的取代基一或二取代:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,乙基磺酰基,三氟甲基,二氟甲氧基,三氟甲氧基,二氟甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基和乙氧基亚氨基乙基。R6和R7各自独立地特别代表甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,三氟甲基,三氟乙基,甲氧基,乙氧基,正-或异-丙氧基,正-、异-、仲-或叔-丁氧基,二氟甲氧基,三氟甲氧基,二氟氯代甲氧基,三氟乙氧基,甲硫基,乙硫基,正-或异-丙硫基,二氟甲硫基,三氟甲硫基,二氟氯代甲硫基,烯丙基,正-或仲-丁烯基;烯丙基氧基,正-或仲-丁烯基氧基,烯丙基硫基,正-或仲-丁烯基硫基;炔丙基,正-或仲-丁炔基;炔丙基氧基;炔丙基硫基;氨基;甲基氨基,乙基氨基,正-或异-丙基氨基,正-、异-、仲-或叔-丁基氨基;二甲基氨基,二乙基氨基,二-正-或异-丙基氨基,甲基乙基氨基,甲基正丙基氨基,甲基异丙基氨基,环丙基氨基,苯基氨基或甲基苯基氨基,代表苯基,苯氧基或苯硫基,这些基团的每一个可以被相同或不同的选自下面的取代基一至三取代:氟,氯,溴,甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,三氟甲基和三氟甲氧基;或者代表环丙基,环戊基,环己基,环丙基氧基,环戊基氧基,环己基氧基,环丙基硫基,环戊基硫基,环己基硫基,环丙基氨基,环戊基氨基,环己基氨基,1-吡咯烷基,1-哌啶基和1-吗啉基,这些基团的每一个可以被相同或不同的选自下面的取代基一至三取代:氟,氯,溴,甲基,乙基,正-或异-丙基和三氟甲基,或者代表吡咯基,呋喃基,噻吩基,吡唑基,咪唑基,噻唑基,异噻唑基,噁唑基,异噁唑基,噁二唑基,噻二唑基,1,2,3-三嗪基,1,2,4-三嗪基,1,3,5-三嗪基,吡啶基,嘧啶基,吡嗪基或哒嗪基,这些基团的每一个可以被相同或不同的选自下面的取代基一或二取代:氟,氯,溴,氰基,硝基,氨基,羟基,甲酰基,羧基,氨基甲酰基,硫代氨基甲酰基,甲基,乙基,正-或异-丙基,正-、异-、仲-或叔-丁基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,甲基磺酰基,乙基磺酰基,三氟甲基,二氟甲氧基,三氟甲氧基,二氟甲硫基,三氟甲硫基,三氟甲基亚磺酰基或三氟甲基磺酰基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基,二乙基氨基,乙酰基,丙酰基,乙酰氧基,甲氧羰基,乙氧羰基,甲基磺酰基氧基,乙基磺酰基氧基,肟基甲基,肟基乙基,甲氧基亚氨基甲基,乙氧基亚氨基甲基,甲氧基亚氨基乙基和乙氧基亚氨基乙基,或者代表吡咯烷基,哌啶基,吗啉基或者哌嗪基,这些基团各自任选被甲基一或二取代。此外,R6和R7与它们所连接的磷原子一起特别代表含有一个或两个其它相同或不同的杂原子例如氧,硫和/或氮,并且可以被相同或不同的选自甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,氯和三氟甲基的取代基一至三取代的5-或6-元杂环基团。
上述一般或优选的基团定义适用于式(I)终产物并且相应地适用于在各种制备情况下需要的起始物或中间体。
本发明优选的化合物还有其中R1,R2,G和A具有上面已经提及的作为优选的这些基团的定义的式(I)的稠合的唑类衍生物与酸的酸加成盐。
可以加入的酸优选包括氢卤酸,例如盐酸和氢溴酸,特别是盐酸,还有磷酸,硫酸,硝酸,一官能和二官能羧酸和羟基羧酸,例如乙酸,马来酸,琥珀酸,富马酸,酒石酸,柠檬酸,水杨酸,山梨酸和乳酸,还有磺酸,例如对甲苯磺酸,1,5-萘二磺酸,糖精和硫代糖精。
优选的本发明化合物还有其中R1,R2,G和A具有上面已经提及的作为优选的这些基团的定义的式(I)的元素周期表主族II至IV和副族I和II和IV至VIII的金属盐与稠合的唑类衍生物的加成产物。
这里特别优选的是铜,锌,锰,镁,锡,铁和镍的盐。这些盐的合适的阴离子是从导致生理耐受加成产物的酸产生的那些。在本发明中特别优选的这类酸是氢卤酸,例如盐酸和氢溴酸,还有磷酸,硝酸和硫酸。
可以提到的本发明物质的例子是下面表1-11中列出的稠合的唑类衍生物。表1其中A代表下面的取代基: 表2其中A代表表1中提到的取代基。表3其中A代表表1中提到的取代基。表4其中A代表表1中提到的取代基。表5其中A代表表1中提到的取代基。表6其中A代表表1中提到的取代基。表7其中A代表表1中提到的取代基。表8其中A代表表1中提到的取代基。表9其中A代表表1中提到的取代基。表10其中A代表表1中提到的取代基。表11其中A代表表1中提到的取代基。
式(II)提供了进行本发明方法(a)需要用作起始物的唑类的一般定义。在式(II)中,R1,R2和G优选或特别具有已经提到的与描述本发明式(I)化合物相关的作为优选的或者作为特别优选的R1,R2和G的那些定义。
式(II)的唑类是已知的(比较,例如Chem.Ber.85(1952)1012,1020;Arch.Pharm.290(1957)20,31;Chem.Ber.60(1927),773;和FR-A2542742)。
式(III)提供了进行本发明方法(a)也需要用作起始物的卤化物的一般定义。在式(III)中,A优选或特别具有已经提到的与描述本发明式(I)化合物相关的作为优选的或者作为特别优选的A的那些定义。X1优选代表氨。
式(III)的卤化物是已知的或者可以通过本身已知的方法制备(比较,例如杂环化学(J.Heterocyclic Chem.)1981,997-1006)。
进行本发明方法(a)合适的稀释剂是所有的惰性有机溶剂。优选使用的是脂肪族、脂环族或芳香族烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或十氢化萘;卤代烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷;醚类,例如乙醚,异丙醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷或茴香醚;酮类,例如丙酮,丁酮,甲基异丁基酮或环己酮;腈类,例如乙腈,丙腈,正-或异-丁腈或苄腈;酰胺类,例如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基甲酰苯胺,N-甲基吡咯烷酮或六甲基磷三酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲亚砜;砜,例如环丁砜,或胺类,例如吡啶。
进行本发明方法(a)的合适的酸结合剂是所有常规无机碱或有机碱。可使用的优选是碱土金属或碱金属的氢化物,氢氧化物,氨化物,醇盐,乙酸盐,碳酸盐或碳酸氢盐,例如氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,乙酸钠,乙酸钾,乙酸钙,碳酸钠,碳酸钾,碳酸氢钾或碳酸氢钠,还有铵化合物,例如氢氧化铵,乙酸铵或碳酸铵,还有叔胺类,例如三甲基胺,三乙基胺,三丁基胺,N,N-二甲基苯胺,N,N-二甲基苯甲胺,吡啶,N-甲基哌啶,N-甲基吗啉,N,N-二甲基氨基吡啶,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
进行本发明方法(a)时,反应温度可以在相当宽的范围内变化。一般情况下,在0℃至150℃之间的温度下进行该反应,优选在20℃至120℃之间的温度下。
进行本发明方法(a)时,对于每摩尔式(II)唑类一般使用1摩尔至15摩尔,优选1至2摩尔,特别优选1至1.3摩尔式(III)的卤化物。通过常规方法进行后处理。
式(I-a)提供了进行本发明方法(b)需要用作起始物的氰基咪唑的一般定义。在该结构式中,R1,R2和A优选或特别具有已经提到的与描述本发明式(I)化合物相关的作为优选的或者作为特别优选的R1,R2和A的那些定义。
式(I-a)的氰基咪唑是本发明化合物,并且可以通过本发明方法(a)制备。
进行本发明方法(b)合适的稀释剂是所有的常规惰性有机溶剂以及水。优选使用的是脂肪族、脂环族或芳香族烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或十氢化萘;卤代烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷;醚类,例如乙醚,异丙醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷或茴香醚;酰胺类,例如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基甲酰苯胺,N-甲基吡咯烷酮或六甲基磷三酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲亚砜;砜,例如环丁砜;胺类,例如吡啶;醇类,例如甲醇,乙醇,正-或异-丙醇,正-、异-、仲-或叔-丁醇,乙二醇,丙烷-1,2-二醇,乙氧基乙醇,甲氧基乙醇,二甘醇一甲基醚,二甘醇一乙基醚,其与水的混合物或者纯水。
进行本发明方法(b)的合适的碱也是所有常规无机或有机酸结合剂。优选使用的是碱土金属或碱金属的氢化物,氢氧化物,氨化物,醇盐,乙酸盐,碳酸盐或碳酸氢盐,例如氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,乙酸钠,乙酸钾,乙酸钙,碳酸钠,碳酸钾,碳酸氢钾或碳酸氢钠,还有铵化合物,例如氢氧化铵,乙酸铵或碳酸铵,还有叔胺类,例如三甲基胺,三乙基胺,三丁基胺,N,N-二甲基苯胺,N,N-二甲基苯甲胺,吡啶,N-甲基哌啶,N-甲基吗啉,N,N-二甲基氨基吡啶,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
进行本发明方法(b)时,反应温度可以在相当宽的范围内变化。一般情况下,在0℃至150℃之间的温度下进行该反应,优选在20℃至120℃之间的温度下。
进行本发明方法(b)时,对于每摩尔式(I-a)氰基咪唑一般使用1摩尔至1000摩尔,优选1至50摩尔的硫化氢。通过常规方法进行反应和后处理。
使用例如1-(噻吩-2-磺酰基)-1H-咪唑并[4,5-b]吡啶-2-硫代甲酰胺和碘甲烷为起始物,则本发明方法(c)的过程可以通过下面的反应式说明:
式(I-b)提供了进行本发明方法(c)需要用作起始物的硫代氨基甲酰基咪唑的一般定义。在该结构式中,R1,R2和A优选或特别具有已经提到的与描述本发明式(I)化合物相关的作为优选的或者作为特别优选的R1,R2和A的那些定义。
式(I-b)的硫代氨基甲酰基咪唑是本发明化合物并且可以通过本发明方法(b)制备。
式(IV)提供了进行本发明方法(c)也需要用作起始物的烷基化试剂的一般定义。在该结构式中,R4优选或特别具有已经提到的与描述本发明式(I)化合物相关的作为优选的或者作为特别优选的R4的那些定义。X2优选代表卤素,甲磺酰基氧基,甲苯磺酰基氧基,R4-O-SO2-O-或R4-O-CO-O-。
式(IV)的烷基化试剂是常规实验室化合物。
进行本发明方法(c)合适的稀释剂是所有的惰性有机溶剂。优选使用的是脂肪族、脂环族或芳香族烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或十氢化萘;卤代烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷或三氯乙烷;醚类,例如乙醚,异丙醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷或茴香醚;酮类,例如丙酮,丁酮,甲基异丁基酮或环己酮;腈类,例如乙腈,丙腈,正-或异-丁腈或苄腈;酰胺类,例如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基甲酰苯胺,N-甲基吡咯烷酮或六甲基磷三酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲亚砜;砜,例如环丁砜,或胺类,例如吡啶。
进行本发明方法(c)的合适的酸结合剂是所有常规无机碱或有机碱。优选使用的是碱土金属或碱金属的氢化物,氢氧化物,氨化物,醇盐,乙酸盐,碳酸盐或碳酸氢盐,例如氢化钠,氨化钠,甲醇钠,乙醇钠,叔丁醇钾,氢氧化钠,氢氧化钾,乙酸钠,乙酸钾,乙酸钙,碳酸钠,碳酸钾,碳酸氢钾或碳酸氢钠,还有铵化合物,例如氢氧化铵,乙酸铵或碳酸铵,还有叔胺类,例如三甲基胺,三乙基胺,三丁基胺,N,N-二甲基苯胺,N,N-二甲基苯甲胺,吡啶,N-甲基哌啶,N-甲基吗啉,N,N-二甲基氨基吡啶,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
进行本发明方法(c)时,反应温度可以在相当宽的范围内变化。一般情况下,在0℃至150℃之间的温度下进行该反应,优选在20℃至120℃之间的温度下。
进行本发明方法(c)时,对于每摩尔式(I-b)硫代氨基甲酰基咪唑一般使用1摩尔至10摩尔,优选1至5摩尔的式(IV)的烷基化试剂。通过常规方法进行后处理。
本发明方法(a),(b)和(c)一般在大气压下进行,但是也可以在高压或低压下进行--一般在0.1巴和10巴之间。
式(I)的稠合的唑类衍生物可以转化为酸加成盐或者金属盐配合物。
为了制备式(I)的化合物的酸加成盐,优选使用已经提到的与描述本发明酸加成盐相关的作为优选的酸的那些酸。
式(I)的化合物的酸加成盐可以以简单的方式通过常规的生成盐的方法获得,例如通过将式(I)的化合物溶解于合适的惰性溶剂中并且加入酸,例如盐酸,其可以用已知的方法分离,例如通过过滤,和,如果适当,通过用惰性有机溶剂洗涤纯化。
为了制备式(I)的化合物的金属盐配合物,优选使用已经提到的与描述本发明金属盐配合物相关的作为优选的金属盐的那些金属盐。
式(I)的化合物的金属盐配合物可以以简单的方式通过常规方法获得,例如通过将金属盐溶解于醇例如乙醇中并且将其加入到式(I)的化合物中。金属盐配合物可以用已知的方法分离,例如通过过滤,和,如果适当,通过重结晶将其纯化。
本发明化合物具有强的杀微生物活性,并且可以用来在农作物保护和材料保护中防治不期望的微生物,例如真菌和细菌。
农作物保护中使用杀真菌剂来防治根肿菌(Plasmodiophoromycetes),卵孢真菌(Oomycetes),壶菌(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌纲(Deutermycetes)。
农作物保护中使用杀细菌剂来防治假单孢菌科(Pseudomonadaceae),根瘤菌科(Rhizobiaceae),肠杆菌科(Enterobacteriaceae),棒状杆菌科(Corynebacteriaceae)和链霉菌科(Streptomycetaceae)。
作为例子可以提到上述属名下的真菌病和细菌病的一些病原体,但是不受此限制:黄单孢菌属种类(Xanthomonas),例如田野稻黄单孢菌变种(Xanthomonas campestris pv.oryzae);假单孢菌属种类(Pseudomonas),例如丁香黄瓜角斑病假单孢菌变种(Pseudomonas syringae pv.lachrymans);欧文氏杆菌属种类(Erwinia),例如解淀粉欧文氏杆菌(Erwiniaamylovora);腐霉属种类(Pythium),例如终极腐霉(Pythium ultimum);疫霉属种类(Phytophthora),例如蔓延疫霉(Phytophthorainfestans);假霜霉属种类(Pseudoperonospora),例如律草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);单轴霉属种类(Plasmopara),例如葡萄生单轴霉(Plasmoparaviticola);盘梗霉属种类(Bremia),例如莴苣盘梗霉(Bremia lactucae);霜霉属种类(Peronospora),例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(Peronospora brassicae);白粉菌属种类(Erysiphe),例如禾白粉菌(Erysiphe graminis);单丝壳菌属种类(Sphaerotheca),例如苍耳单丝壳菌(Sphaerothecafuliginea);柄球菌属种类(Podosphaera),例如苹果白粉病柄球菌(Podosphaeraleucotricha);黑星菌属种类(Venturia),例如苹果黑星菌(Venturia inaequalis);核腔菌属种类(Pyrenophora),例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(Pyrenophora graminea)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));旋孢菌属种类(Cochliobolus),例如禾旋孢菌(Cochliobolussativus)(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));单胞锈菌属种类(Uromyces),例如疣顶单胞锈菌(Uromycesappendiculatus);柄锈菌属种类(Puccinia),例如隐匿柄锈菌(Puccinia recondita);核盘菌属种类(Sclerotinia),例如油菜核盘菌(SclerotiniaSclerotiorum);腥黑粉菌属种类(Tilletia),例如小麦网腥黑粉菌(Tilletiacaries);黑粉菌属种类(Ustilago),例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);薄膜革菌属种类(Pellicularia),例如佐佐木氏薄膜革菌(Pellicularia sasakii);Pyricularia种类,例如Pyricularia oryzae;镰孢属种类(Fusarium),例如大刀镰孢(Fusarium culmorum);葡萄孢属种类(Botrytis),例如灰色葡萄孢(Botrytis cinerea);壳针孢属种类(Septoria),例如颖枯壳针孢(Septoria nodorum);小球腔菌属种类(Leptosphaeria),例如颖枯小球腔菌(Leptosphaeria nodorum);尾孢属种类(Cercospora),例如Cercospora canescens;链格孢属种类(Alternaria),例如甘蓝黑斑病链格孢(Alternariabrassicae);假尾孢属种类(Pseudocercosporella),例如Pseudocercosporellaherpotrichoides。
植物对在防治植物病害所需要的浓度时的活性化合物具有好的耐受性的事实允许处理植物的地上部分,植物繁殖根株和种子,和处理土壤。
本发明活性化合物特别成功地用于防治水果和蔬菜生长和葡萄栽培中的病害,例如抗疫霉(Phytophthora)属。
本发明化合物也可以用来提高农作物产量。此外,它们表现出减小的毒性并且为植物所很好耐受。
根据其特定的物理和/或化学性质,活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂,包裹在聚合物中和在用于种子的包被组合物中的细微胶囊以及ULV冷雾和热雾制剂。
这些型剂可以用已知的方式制备,例如,通过将活性化合物与扩充剂即液体溶剂,加压液化气体和/或固体载体混合,任选地使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。如果使用的扩充剂是水,则也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳香族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲亚砜,以及水;液化气体扩充剂或载体理解为指常温常压下是气体的液体,例如气雾抛射剂,例如卤代烃,还有丁烷,丙烷,氮和二氧化碳。适合的固体载体是:例如磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的适合的固体载体是:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂是:例如,木素亚硫酸盐废液和甲基纤维素。
制剂中,可以使用增粘剂如羧甲基纤维素、天然和合成的粉状、颗粒或乳胶形式的聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它可能的添加剂是矿物油和植物油。
也可以使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%之间。
根据其特定的物理和/或化学性质,活性化合物可以配制成常规制剂,例如溶液、乳剂、悬浮剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂,包裹在聚合物中和在用于种子的包被组合物中的细微胶囊以及ULV冷雾和热雾制剂。
本发明活性化合物可以以本身使用,或者以其制剂使用,也可以与已知的杀真菌剂,杀细菌剂,杀螨剂、杀线虫剂或杀昆虫剂混合使用,例如以扩大作用范围或者防止抗药性产生。在很多情况下这样会导致增效作用,即混合物的活性超过了各个组分的活性。
混合物中共同成分的例子是下面的化合物:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoprim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacril-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,epoxyconazole,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,ipconazole,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,coppernaphthenate,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,氯吡呋醚,
Quinconazel,五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,调环烯,氟嘧唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
zarilamide,代森锌,福美锌,还有
Dagger G,
OK-8705,
OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-a-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基]-氨基甲酸异丙酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)乙酮-O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘代甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷酮,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-N-碳酰苯胺,
2,6-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
硫代氰酸2,6-二氯-5-(甲硫基)-4-嘧啶酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]苯甲酰胺,
2-(2,3,3-三碘代-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-a-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴代甲基)戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫氰酸根合甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)-氧基]-甲基]苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈),
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-噻吩二羧酸酯,
顺-1-(4-氯代苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉]盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲亚氨酰胺,
N-甲酰基-N-羟基-DL-丙氨酸一钠盐,
硫代氨基磷酸[2-(二丙基氨基)-2-氧代乙基]-乙酯O,O-二乙酯,
硫代氨基磷酸O-甲酯S-苯酯苯酯丙酯,
1,2,3-苯并噻二唑-7-硫代甲酸S-甲酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
杀细菌剂:
bronopol,双氯酚,氯甲基吡啶,二甲基二硫代氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,阿凡曼菌素,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,
苏云金杆菌,4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-1H-吡咯-3-腈,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,chloethocarb,chlorethoxyfos,chlorfenapyr,毒虫畏,定虫隆,氯甲硫磷,N-[(6-氯-3-吡啶基)-甲基]-N’-氰基-N-甲基-乙亚胺酰胺,毒死蜱,甲基毒死蜱,顺式-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,
甲基毒虫畏,敌噁磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,噁唑磷,异阿凡曼菌素,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,
二溴磷,NC184,nitenpyram,
氧乐果,杀线威,亚砜吸磷,异砜磷,
对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyradaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,
tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,zetamethrin。
也可以是与其它已知的活性化合物例如除草剂,肥料和生长促进剂的混合物。
活性化合物可以使用其自身或者以其制剂形式使用或者以从中制备的使用形式使用,例如即用型溶液,混悬剂,可湿粉剂,糊剂,可溶粉剂,细粉剂和颗粒剂。以常规方法使用,例如通过浇灌,喷雾,弥雾,散播,发泡,刷涂在其上等。此外还能通过超低体积方法施用活性化合物,或者将活性化合物制剂或活性化合物本身注入土壤。也可以处理植物的种子。
当使用本发明活性化合物作为杀真菌剂时,施用比例可以在相当宽的范围内变化,取决于施用方法。处理植物部分时,活性化合物施用比例一般是0.1和10000g/ha之间,优选在10-1000g/ha之间。在处理种子时,活性化合物施用比例一般是每千克种子用0.001-50g,优选0.01-10g。处理土壤情况下,活性化合物施用比例一般是0.1和10000g/ha之间,优选在1和5000g/ha之间。
向40ml无水四氢呋喃中2.5g(15mmol)1H-咪唑并[4,5-b]吡啶的溶液中加入0.3g(10mmol)氢化钠(80%强度的矿物油悬浮液),混合物在20℃下搅拌10分钟。然后加入3.0g(15mmol)3,5-二甲基异噁唑-4-磺酰氯,混合物在20℃下又搅拌20小时,将反应混合物倒入200ml水中,得到的混合物萃取两次,每次用150ml乙醚。合并的有机相用硫酸钠干燥并减压浓缩。残余物经硅胶色谱,用乙醚洗脱。得到1.3g(理论量的46%)1-(3,5-二甲基-异噁唑-4-磺酰基)-1H-咪唑并[4,5-b]吡啶,为白色固体,熔点为77-80℃。实施例2方法(a)
向30ml乙腈中1.2g(10mmol)1H-咪唑并[4,5-c]吡啶的溶液中加入1.4g(10mmol)碳酸钾,混合物在20℃下搅拌10分钟。然后混合物与1.9g(10mmol)3,5-二甲基异噁唑-4-磺酰氯混合并且在20℃下又搅拌20小时,将反应混合物接着倒入150ml水中,得到的混合物萃取两次,每次用70ml乙酸乙酯。合并的有机相用硫酸钠干燥并减压浓缩。残余物与20ml石油醚搅拌,过滤得到的固体并干燥。得到1.6g(理论量的57%)1-(3,5-二甲基-异噁唑-4-磺酰基)-1H-咪唑并[4,5-c]吡啶,为黄色固体,熔点是130-135℃。
通过上面给出的方法制备下面表12中列出的化合物:表12: 表12:(续) *)1H-NMR谱是在氘代氯仿(CDCl3)或六氘代二甲亚砜(DMSO-d6)中,使用四甲基硅烷(TMS)为内标记录的。化学位移δ值以ppm表示。应用实施例实施例A单轴霉(Phasmopara)试验(葡萄)/保护性的溶剂: 47份重量丙酮乳化剂: 3份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和乳化剂混合,用水将乳油稀释到需要的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂对幼小植物喷雾。喷雾层风干后,用葡萄生单轴霉(Phasmopara viticola)的孢子水悬浮液接种植物。然后将植物放置在大约20℃和100%相对空气湿度的培养室中一天。然后将植物放置在大约21℃和大约90%相对空气湿度的温室中五天。然后弄温植物并在培养室中放置一天。
接种后6天进行评估。0%指相当于对照物的效力,而100%的效力指没有发现侵染。
下面的表中给出了活性化合物,施用比例和试验结果。
为了制备活性化合物的合适的制剂,将1份重量活性化合物与所述量溶剂和乳化剂混合,用水将乳油稀释到需要的浓度。
为了试验保护活性,以所述施用比例用活性化合物制剂对幼小植物喷雾。喷雾层风干后,用苹果黑星菌(Venturia inaequalis)的致病生物体的分生孢子水悬浮液接种植物。然后将植物放置在大约20℃和100%相对空气湿度的培养室中一天。
然后将植物放置在大约21℃和大约90%相对空气湿度的温室中。
接种后12天进行评估。0%指相当于对照物的效力,而100%的效力指没有发现侵染。
下面的表中给出了活性化合物,施用比例和试验结果。
表B黑星菌试验(苹果)/保护性的
Claims (10)
其中
R1和R2与它们所连接的碳原子一起代表任选被取代的杂环或者代表任选被取代的苯稠合的杂环,
G代表氮或者基团
其中
其中
Y代表氧或硫,
R5代表任选被取代的不饱和的杂环基团,
R6和R7各自独立地代表烷基,卤代烷基,烷氧基,卤代烷氧基,烷硫基,卤代烷硫基,链烯基,卤代链烯基,链烯基氧基,链烯基硫基,炔烃基,炔烃基氧基,炔烃基硫基,任选被烷基-、环烷基-或芳基-取代的氨基,任选被取代的芳基,任选被取代的芳基氧基,任选被取代的芳基硫基,任选被取代的环烷基,任选被取代的环烷基氧基,任选被取代的环烷基硫基或者代表任选被取代的饱和的或不饱和的杂环基团,或者
R6和R7与它们所连接的磷原子一起代表任选被取代的杂环基团。
2.制备权利要求1的式(I)的稠合的唑类衍生物以及它们的酸加成盐和金属盐配合物的方法,特征在于
其中
R1,R2和A如上定义,
或者
R4-X2 (IV)
其中
R4如上定义,和
X2代表离去基团,
以及如果适当,向得到的式(I)的化合物中加入酸或金属盐。
3.杀微生物组合物,特征在于,其中除了含扩充剂和/或表面活性剂外还含有至少一种权利要求1的式(I)的稠合的唑类衍生物或者式(I)的稠合的唑类衍生物的酸加成盐或金属盐配合物。
4.权利要求1的式(I)的稠合的唑类衍生物或者其酸加成盐或金属盐配合物作为杀微生物剂在农作物保护和材料保护中的用途。
5.在农作物保护和材料保护中防治不期望微生物的方法,特征在于对微生物和/或其栖息地施用权利要求1的式(I)的稠合的唑类衍生物或者其酸加成盐或金属盐配合物。
6.制备杀微生物剂组合物的方法,特征在于,将权利要求1的式(I)的稠合的唑类衍生物或者其酸加成盐或金属盐配合物与扩充剂和/或表面活性剂混合。
8.权利要求1的稠合的唑类衍生物,特征在于,其具有下面的结构式
9.权利要求1的稠合的唑类衍生物,特征在于,其具有下面的结构式
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19708688A DE19708688A1 (de) | 1997-03-04 | 1997-03-04 | Annellierte Azolderivate |
DE19708688.8 | 1997-03-04 |
Publications (1)
Publication Number | Publication Date |
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CN1249752A true CN1249752A (zh) | 2000-04-05 |
Family
ID=7822140
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN98803033A Pending CN1249752A (zh) | 1997-03-04 | 1998-02-19 | 用作杀微生物剂的稠合的唑类衍生物 |
Country Status (11)
Country | Link |
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US (3) | US6214840B1 (zh) |
EP (1) | EP0966467A1 (zh) |
JP (1) | JP2001513783A (zh) |
KR (1) | KR20000071079A (zh) |
CN (1) | CN1249752A (zh) |
AU (1) | AU6297298A (zh) |
BR (1) | BR9808142A (zh) |
CZ (1) | CZ312699A3 (zh) |
DE (1) | DE19708688A1 (zh) |
PL (1) | PL335462A1 (zh) |
WO (1) | WO1998039331A1 (zh) |
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DE10063116A1 (de) * | 2000-12-18 | 2002-06-20 | Bayer Ag | Azinylsulfonylimidazole |
US6990912B2 (en) | 2001-02-28 | 2006-01-31 | Arysta Lifescience North America Corporation | Subsurface soil injection apparatus |
US7998500B2 (en) | 2005-08-04 | 2011-08-16 | Vertical Pharmaceuticals, Inc. | Nutritional supplement for women |
US7901710B2 (en) | 2005-08-04 | 2011-03-08 | Vertical Pharmaceuticals, Inc. | Nutritional supplement for use under physiologically stressful conditions |
US8202546B2 (en) | 2005-08-04 | 2012-06-19 | Vertical Pharmaceuticals, Inc. | Nutritional supplement for use under physiologically stressful conditions |
US8263137B2 (en) | 2005-08-04 | 2012-09-11 | Vertical Pharmaceuticals, Inc. | Nutritional supplement for women |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2542742B1 (fr) | 1983-03-16 | 1985-06-28 | Rhone Poulenc Agrochimie | Nouveaux derives de cyano-2 imidazo (4,5-b) pyridine. leur preparation et leur utilisation comme fongicides |
DE3605714A1 (de) | 1986-02-22 | 1987-08-27 | Bayer Ag | Mikrobizide mittel |
ATE104286T1 (de) * | 1990-06-21 | 1994-04-15 | Ciba Geigy Ag | Benzotriazol-1-sulfonylderivate mit mikrobiziden eigenschaften. |
US5322853A (en) | 1990-06-21 | 1994-06-21 | Ciba-Geigy Corporation | Microbicidal benzotriazole compounds |
DE4302461A1 (de) | 1993-01-29 | 1994-08-04 | Bayer Ag | Fluorierte Benzotriazole |
US5369086A (en) | 1993-04-28 | 1994-11-29 | Zeneca Limited | N-benzotriazoles |
DE19513990A1 (de) * | 1995-04-13 | 1996-10-17 | Bayer Ag | Benzimidazol-Derivate |
DE19523446A1 (de) * | 1995-06-28 | 1997-01-02 | Bayer Ag | Benzotriazole |
HUP9802822A3 (en) * | 1995-08-10 | 1999-04-28 | Bayer Ag | Halobenzimidazol derivatives, intermediates, preparation thereof and microbocide compositions containing these compounds as active ingredients |
-
1997
- 1997-03-04 DE DE19708688A patent/DE19708688A1/de not_active Withdrawn
-
1998
- 1998-02-19 US US09/380,502 patent/US6214840B1/en not_active Expired - Fee Related
- 1998-02-19 WO PCT/EP1998/000942 patent/WO1998039331A1/de not_active Application Discontinuation
- 1998-02-19 CZ CZ993126A patent/CZ312699A3/cs unknown
- 1998-02-19 EP EP98906961A patent/EP0966467A1/de not_active Withdrawn
- 1998-02-19 JP JP53809998A patent/JP2001513783A/ja active Pending
- 1998-02-19 KR KR1019997007366A patent/KR20000071079A/ko not_active Application Discontinuation
- 1998-02-19 CN CN98803033A patent/CN1249752A/zh active Pending
- 1998-02-19 BR BR9808142-0A patent/BR9808142A/pt not_active IP Right Cessation
- 1998-02-19 AU AU62972/98A patent/AU6297298A/en not_active Abandoned
- 1998-02-19 PL PL98335462A patent/PL335462A1/xx unknown
-
2001
- 2001-01-29 US US09/772,042 patent/US6387922B2/en not_active Expired - Fee Related
-
2002
- 2002-03-18 US US10/100,419 patent/US6569869B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
BR9808142A (pt) | 2000-03-28 |
DE19708688A1 (de) | 1998-09-10 |
EP0966467A1 (de) | 1999-12-29 |
JP2001513783A (ja) | 2001-09-04 |
PL335462A1 (en) | 2000-04-25 |
WO1998039331A1 (de) | 1998-09-11 |
US6387922B2 (en) | 2002-05-14 |
US6214840B1 (en) | 2001-04-10 |
US20020143184A1 (en) | 2002-10-03 |
CZ312699A3 (cs) | 1999-12-15 |
US20010029237A1 (en) | 2001-10-11 |
KR20000071079A (ko) | 2000-11-25 |
US6569869B2 (en) | 2003-05-27 |
AU6297298A (en) | 1998-09-22 |
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