TW318829B - - Google Patents
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- TW318829B TW318829B TW084102527A TW84102527A TW318829B TW 318829 B TW318829 B TW 318829B TW 084102527 A TW084102527 A TW 084102527A TW 84102527 A TW84102527 A TW 84102527A TW 318829 B TW318829 B TW 318829B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- coome
- pyridyl
- alkyl
- meo
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 241000233866 Fungi Species 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- -1 benzyloxy, morpholinyl Chemical group 0.000 claims description 39
- 238000011049 filling Methods 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- 125000005554 pyridyloxy group Chemical group 0.000 claims 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000004354 sulfur functional group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 abstract description 4
- 230000000120 cytopathologic effect Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000002184 metal Chemical class 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 108
- 230000008018 melting Effects 0.000 description 19
- 238000002844 melting Methods 0.000 description 19
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 241000123650 Botrytis cinerea Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002079 cooperative effect Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- NVDJVEQITUWZDT-UHFFFAOYSA-N 6-Methoxy-pyridine-3-carboxylic acid Chemical compound COC1=CC=C(C(O)=O)C=N1 NVDJVEQITUWZDT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 241000233614 Phytophthora Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 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 2
- 238000010410 dusting Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000003147 glycosyl group Chemical group 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 1
- KHMNCHDUSFCTGK-UHFFFAOYSA-N 2-aminophenylacetic acid Chemical compound NC1=CC=CC=C1CC(O)=O KHMNCHDUSFCTGK-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- BQKCABNKOFEHEG-UHFFFAOYSA-N 5H-dioxazole Chemical compound O1ON=CC1 BQKCABNKOFEHEG-UHFFFAOYSA-N 0.000 description 1
- UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 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 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000162682 Heterogen Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 238000012351 Integrated analysis Methods 0.000 description 1
- 241000228456 Leptosphaeria Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000201282 Limonium Species 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
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- 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
- A01N43/06—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 five-membered rings
- A01N43/10—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 five-membered rings with sulfur as the ring hetero atom
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
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- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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Description
318829 Α7 Β7 i、發明説明( 本發明闞於用作殺真菌劑的新穎鄰胺基苯甲酸衍生物。 前吐坊越 GB 1,563,664及日本公告(Japanese Kokai> —53130655 號掲示鄰胺基苯甲酸酯的殺真菌劑。發明人發現特定的新 穎鄰胺基笨甲酸衍生物也具有價值的殺真菌活性’且其優 點勝於此等公告所揭示的化合物。 太發明根示 根據本發明,提供一種式I化合物
(I) (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局負工消費合作社印製 其中 X是 A是 R1是 0或S ; 含至少一個氮原子的6員的雜芳基,視需要可被一 或多個R 2基圑取代; 烷基,環烷基,環烯基,烯基*炔基或胺基’(每 一此等基圑可視需要經取代)、η ,鹵素’氰 基,硝基,醯基,醯氧基,視需要經取代的苯基; 或二個相鄱基圑與其相聯的碳原子共同形成苯并環 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(2 ) 9 R2之 意義與R1同,或二僩相鄰的與其相脚的碳原子共同 形成視需要取代的雜環; Y是 烷基•環烷基,環烯基,烯基或炔基,每一此等基 團可視需要經取代,氫或醢基; Y1之 意義與Y同*或是視需要經取代的苯基或是視需要 取代的雜瑁; Z是 CkXM-X^-R3,氰基,硝基,胺基•醣基•視需要 取代的雜環,-(:(1?6)=1^-01^或-(:(1^>=»1-«1^117; R3是 烷基,環烷基,環烯基> 烯基》炔基》苯基或雜環 •每一此等基團可視需要經取代,氫或無機或有機 陽離子基團; X1及 X2,可相同或相異•是0或S; R6, Re&R7,可相同或相異,是烷基,環烷基,瑁烯基 ,烯基,炔基,笨基或雜瓖,每一此等基圈可視需 要經取代·或氫或Re&R7與其相聯的碳原子共同形 成一環; η是 0至4 ; 及與金鼸鼸形成的錯合物,Μ及與_所成的《(當化合物 為酸)及與酸所成的篇(當化合物為,前題是在Υ為 氫且 i ) ζ為羧基,甲氧羰基或乙氧羰基時,環Α不是未經取 代的吡啶基或吡畊基;而 ϋ >在ζ為羧基且1»是0時,A不是2-氣-4-吡啶基· &-( 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) I-----:--------iT (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印裝 A7 B7 五、發明説明(5 ) 2-二乙胺乙氧基)-3-吡啶基或2-吡啶基。 烷基較佳是1至20個•例如1至6個•破原子的。烯基及 炔基一般是3至6個碳原子。環烷基或環烯基較佳是3至6個 碳原子。 取代基,在見於烷基、環烷基、環烯基、烯基或炔基上 時,包括鹵素,叠篦基,氰基,視需要取代的烷氧基,視 需要取代的烷硫基,羥基,硝基,視需要取代的胺基*醣 基,醣氧基*視裔要取代的苯基,視需要取代的雜環,視 需要取代的苯氧基及視需要取代的_環氧基。 瑁烷基及環烯基也可K烷基取代。 見於任何苯基上的取代基一般是一或多僩如R1所界定的 基團。 雑環一詞包括芳香族及非芳香族雑瓖基團。雜環基團一 般是5,6或7員的環,含達4個選自氮,氧,及硫的雜原 子。雜瑁基圈的例是呋喃基,噻盼基*吡咯基•吡咯啉基 ,吡咯啶基,眯唑基*二氧戊瓌基·噚唑基*噻唑基,眯 唑基,咪唑啉基,咪唑啶基,吡唑基,吡唑啉基,吡唑啶 基,異嗶唑基,異噻唑基,嗶二唑基•三唑基,_二唑基 *吡喃基•吡啶基,六氫吡啶基•二嗶烷基,嗎福啉基· 吡畊基,六氫吡畊基,三畊基*噻唑啉基》苯并眯唑基, 四唑基,苯并噚唑基*眯唑吡啶基,1,3-笨并噚畊基· 1,3-苯并噻畊基,嗶唑吡啶基,笨并呋哺基,《明:基•枝 唑啉基,晻喔唞基,環丁礪基•二簋_唑啉基,苯并_唑 基,酞皤亞胺基•苯并呋喃基•吖庚因基及苯并二13 丫庚因 -6 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210 X 297公嫠) -------:—:士衣— (請先閲讀背面之注意事項再填寫本頁) 訂 318629 at Β7 i、發明説明(4 ) 基° 雜瑁基團本身也可是取代的,如取代的苯基。 胺基可由,例如•一或二個視霈要取代的烷基或醢基所 取代,或二個取代基形成一環,較佳是5 -至7 -員的環,而 此等環也可是取代的,並含其他雜原子,例如嗎福啉*硫 代嗎福啉或六氫吡啶。 醮基一詞包括硫及含磷的酸或羧酸的殘基。釀基的例是 -CORB · -COOR8 · -CXHRBRe · -CON (RB)ORe · -C00NRBRe ,-COH (RB)HReR7 ,-COSR6,-CSSRB ♦ -S (0)PRB · -S(0)z0R5 » -S(0)pNRBRe » -P ( =X) (0RB) (0Re) · -C0-C00Re ,其中RB· ReRR7之定義如前述*或1^及1{7與 其相聪的原子共同形成一環,P是1或2,而X是OSS。 A —般較佳是吡啶(尤其是3-吡啶基>·嘧啶(尤其是 5-嘧啶基),或吡畊環。A也可是,例如四畊*吡畊或三 畊環。 R2較佳是選自鹵素,尤其是氟,或烷基,尤其是甲基。 f較佳是(ΜζΧΜ-Χ2-!?3,X1及X2較佳都是0,R—般是烷基 ,烯基或炔基•每一此等基團是視需要取代的•特別是甲 基。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) Υ較佳是氫•烷基,尤其是甲基或醮基*尤其是烷醣基 或烷氧醣基。 X較佳是0 。 η較佳是0 。 本發明的此等化合物一般是由式Han 2的Μ形成*其中Μ 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X297公釐) 經濟部中央橾準局員工消貧合作社印製 A7 B7 五、發明説明(5 ) 為二價金靨陽離子,例如網錳、鈷,鏵、嫌或鋅,而An為 陰雄子,例如氯化合物,硝酸嬲或碕酸鹽。 本發明化合物對多種原自半知菌類、子囊菌類、藻狀菌 類、及擔子菌類的病原菌都有抗菌活性•特別是對植物的 真菌疾病*如霉病*特別是大麥白粉病(Erysiphe graeinia) * 黃瓜白粉病(Erysiphe cichoracaeruB) 及葡 萄箱霉病 (Plasaopara viticola及 Uncinula necator) · 稻瘟病(Pyricularia oryzae),毅 BBSS (P s e u d o c e r c o s p o r e 1 1 a h e r* p o t r i c h i d o s ),稻鞴疫病 (Pellicularia sasakii),灰霉病(Botrytis cinerea), 小麥棟銹病(Pucinia recondita) *晩期蕃S3或馬铃薯疫 病(P h y t o p h t h o r a i n f e s t a n s ) * 蘋果瘡痂病(V e n t u r* i a inaequalis)及穎斑病(Leptosphaeria nodorum)。可能 有些化合物只對幾種病原菌有效,其他的有廣效活性· 有些式I化合物具有弱殺蟲活性·但仍可用作中間»· 而此類化合物也是本發明的一方面。 本發明化合物一般調配成殺真菌的傅統姐合物。此等姐 合物可含一種或多種農藥,例如具餘草性質的、殺真菌性 質的、殺昆盡性質的、殺滿性霣的或殺線蟲性質的化合物 Ο 本發明姐合物中的稀釋劑或載劑可以是固體或液體,視 需要加有界面活性劑,例如分散劑•乳化劑或增湄劑。合 適的界面活性劑包括陰離子化合物*例如羧酸化合物•長 - 8 - 本紙張尺度適用中國國家梯準(CNS > A4規格(210X297公釐) -------:---A------1T (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(6 ) 鏈腊肪酸的羧酸金靨;釀基肌胺酸鹽,帶有脂肪酵乙氧 基化合物的單一或二一磷酸酯或此等酯的鼸;硫酸麵腊肪 酵,如十二烷基疏酸納•十八烷基硫酸納或十六烷基硫酸 納;乙氣化腊肪酵疏酸獼•,乙氧化烷酚基醃酸釀;磺酸木 素;磺酸石油;磺酸烷基芳基酯如烷基笨磺酸酯或低烷基 奈磺酸酯,例如丁基奈磺酸酯;磺酸奈一甲醛箱合物;磺 酸化酚一甲醛縮合物的鹽;或更複嫌的磺酸酿如纗胺磺酸 _,例如油酸及H -甲基牛磺酸磺酸化縮合物或二烷基磺基 丁二酸_,例如二辛基丁二酸磺酸納。非鐮子劑包括脂肪 酸酯、脂肪醇、脂肪酸醯胺或脂肪烷基或烯基取代的酚與 環氧乙烷的縮合產物*多羥基酵酯的脂肪《,例如山梨糖 酵脂肪酸酯*此等酯與環氧乙烷的縮合物*例如聚環氧乙 烷山梨糖醇脂肪酸酯•環氧乙烷輿氧化丙烯的嵌共聚物, 炔靨二酵如2,4,7,9-四甲基-5-癸炔-4,7-二酵,或乙氧 化炔二酵。陽離子界面活性麵的例包括•例如,胞肪族單 一、二一或多胺醋酸酷•環烷酸酯、或油酸醮;含氧的胺 如氧化胺或聚氧乙烯烷基胺;由羧酸輿二-或多胺縮合製 成的聯结釀胺的胺;或四级銨鼸。 本發明姐合物可Μ此技藉所已知的任何雇蕖爾形*如溶 液·分散液•水性乳液,撒粉,種子包衣(seed dressing),滅蒸劑》煙霧劑(3«1〇156),可分散的粉,可 乳化的湄縮物*或頼粒。此外,也可Μ是通於直接使用的 形式,或者是澹縮物或初鈒姐合物,在使用前遴量的水或 其他稀釋劑稀釋。 -9 - 本紙張尺度適用中國國家橾準(CNS ) Α4規格(210X297公嫠) -------:---*衣------、訂 (請先閲讀背面之注意事項再填寫本頁) 318829 A7 _B7_ 五、發明説明(7 ) 作為分散液時,此類姐合物係由本發明化合物分散於液 體介質(較佳是水)内構成。供應使用者時較佳是初鈒姐 合物*此姐合物可用水稀釋成所需溻度的分散液。初級姐 合物可以下述任何形式供應。可Μ是含有溶於可與水混溶 的溶劑内的本發明化合物,並加有分散爾。另一種是含有 磨成细粉的本發明化合物及分散劑•與水均勻混合物成期 或霜*必要時可加於水包油的乳液中,形成水性油乳液内 有有效成分的分散液。 可乳化的濃縮物含有不與水混溶的溶麵内的本發明化合 物及乳化劑•與水混合物時形成乳液。 撒粉含有本發明化合物及與其均勻混合的粉末稀釋_ * 例如高領土。 顆粒固體含有本發明化合物及類似用於擔粉的稀釋劑· 但此混合物係用已知方法製成頼粒。或者是將有效成分吸 附於預先製成的顆粒稀釋劑上*例如吸附於傅勒式土 (Ful. ler’s earth>±,美 _活性白土(attagulgite)上或 石灰石沙上。 可濕的粉一般含有效成分、合缠的界面活性劑及惰性粉 稀釋劑(如瓷土)。 經濟部中央橾準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 另一合4的濃縮物*特別是在產物為固體時*是可流動 的懸浮液濃縮物,此係由磨碎此化合物、水、增濕爾及懸 浮劑製成。 本發明組合物中有效成分的濃度較佳是在1至30重量百 分比範圔内,尤佳是在5至30重量百分比範画内。初級姐 -10 - 本紙張尺度適用中國國家梂準(CNS ) A4规格(210Χ:297公釐)
A7 B7 五、發明説明(8 ) 合物中有效成分的量的變化範圍很大,例如,可佔姐合物 重量的百分之5至95。 本發明化合物可用已知方式製備,例如,用式II化合物 (II) 與式111化合物反應 0
II (III) ---.I^-- (請先閱讀背面之注意事項再填寫本頁) 訂 其中Q是離去基,較佳是鹵素,尤其是氯*產生式I化合 物,其中X是0,Y是氫,如有必要將此化合物用已知方法 修改,生成另一化合物,其中X及 /或γ有另外所需的值, 如有必要再將式I化合物用已知方法改成另一化合物,其 中R1,R2及Z有其他值。 化合物II及III之間的反應一般是在有鹼(例如有機三 级胺〉之存在下在溶劑(如醚)内進行。 化合物II及III是已知的或可用已知方法製備的。 所得式I化合物可用已知方式修改成另一式1化合物, 即是將基團之一修改成另一所需基團° 例如,可用已知方法將醋轉化成自由態的酸或鹽。 11 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) -良· 經濟部中央標準局負工消費合作社印装 Α7 Β7 五、發明説明(9 ) 疏代基圄可用氧化劑•如-氯過苯甲酸,氧化成亞磺釀 基或磺醯基。 炭基可藉已知方法*例如用勞孫式(Lawesson)試劑或五 碲化磷,硫化成硫代炭基。 以合缠的羥基或氫碕基化合物反應,A環上的烷磺醢基 可由合遘的親核基(如芳氧基或芳确基 > 代替。 本發明Μ下述實例說明。分雕出的新穎化合物構造係用 元素及/或其他合遘的分析箱實。溫度Kt:表示。 ------------ 装-- (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 將三乙基胺(28.4克)加於6-氯菸_酸(40克> 於無水 二氣甲烷( 900毫升)内之溶液中。此混合物於冰浴内冷 卻,滴加氛甲酸甲_( 26.8克)。此混合物於室通播拌過 夜*輪流用水、碳酸氫納水溶液及鹽水洗。有機相於碲酸 鎂上乾嫌,遇濾•蒸發,得6-菸_酸甲_。 將10克此產物加於甲酵納(由1.61克納及100毫升甲酵 製得)中。此混合物於回流下加熱3小時·於室溫靜置過 夜。加氫氧化鉀水溶液(10克氫氧化鉀於30奄升水内> * 再將此混合物於回流加熱8小時。再於室溫靜置過夜,蒸 發*將殘餘物加於水(120毫升)内。用鹽酸將混合物酸 化至出3。遇濾沉澱物,乾煉,得6-甲氧基菸_酸*熔點 175 — 177 υ 〇 將此酸(6克)與超董之亞硫醢氣於回流加熱2小時。 將混合物冷卻,蒸發•將殘餘物(含粗製6-甲氧基菸鐮醣 -12 - 本紙張尺度適用中國國家標準(CNS ) Α4规格(210X297公釐> 、?τ 經濟部中央揉準局員工消費合作社印製 A 7 B7 五、發明説明(10 ) 氛)溶於無水四氫呋喃(10奄升)内。將此溶液滴加於鄰 胺基笨甲酸甲酯(6.22克)及三乙基胺(7.92克)於四氫 呋喃( 200毫升)内之溶液中。此混合物於室通攪半《夜 ,蒸發* 酸乙_萃取。萃取物用水洗*乾嫌並蒸發, 殘餘物於二氧化矽膠柱上作色層分析純化*製得(6 -甲 氧基菸《8(醣基 > 鄰胺基笨甲酸甲醮•熔黏121-3。(化合物 1) ° Μ類似方式製得Η- (2-甲磙基-5-唯啶羰基)鄹胺基苯 甲酸甲«,熔點166-8。(化合物la> 。 奮例___2. 將氫化納(0.15克*60X的於油内之溶液)加於由實例 1所得化合物(1克)於無水四氫呋喃(25毫升)内之已 於冰浴上冷卻之溶液中。將此混合物攪拌2 0分鐘·然後加 甲基碘(0.44毫升 > 。此混合物於室溫播拌48小時*蒸發 •用_酸乙酷萃取。萃取物輪流用水及鹽水洗,於确酸鎂 上乾嫌,蒸發。殘餘物於二氧化矽膠柱上作色層分析純化 ,製得N- ( 6-甲氧菸鐮醣基> 甲基邮胺基苯甲酸甲酯 ,熔黏68-70。。(化合物2) 於由實例2所製化合物2 (0.6克)於乙酵(20毫升) 内之溶液中加氯化鋦(11)(0.134克 > 。將混合物靜置過 夜,蒸發,殘餘物用酷酸乙醏研磨,製得贰一〔甲基N-( -13 - 本紙張尺度適用中國國家橾準(CNS ) Α4規格(210X297公釐) --------I Λ-- (請先閲讀背面之注意事項再填寫本頁) 訂 良. 318829 at Β7 五、發明説明(11) 6 -甲氧基菸鹺醐基> -N-甲基郾胺基笨甲酸_〕氛化鋦 (II)錯合物*熔點196-8β。(化合物3> 例-^ 將B-氯遇苯甲酸(13.7克)在播拌下加於化合物la(6 克)於二氛甲烷内之溶液中。此混合物於室溫攪拌過夜· 加硫酸納,用二氮甲烷萃取。萃取物經處理後得N- (2 -甲 磺醣基-5-嘧啶羰基)鄰胺基笨甲_甲_ *熔點187-9°。 (化合物4) 將氫化納(0.24克*60X内的於油内之溶液)加於2-駑 硫基吡啶(0.33克)於無水二甲基甲釀胺(20亳升)内之 溶液中。此混合物於室溫攪拌半小時。在攫拌下滴加化合 物4 (1克)於無水二甲基甲醣胺(20毫升)内之溶液。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 此混合物於室溫攪拌遇夜。冷卻,用甲酵使停止反應。將 混合物倒入水内,用稀鹽酸使成酸性。收取沉澱物,溶於 二氯甲烷内,此溶液用蘧水洗,蒸發,得H-〔2- (2-吡啶 碕基)-5-嘧啶羰基〕一鄰胺基笨甲_甲_,熔點145-147° (化合物 5) 以類似方式,使用碳酸鉀代替氫化納作_,製得N-〔 2- (4-甲氧苯氧基> -5-嘧啶羰基)一鄰胺基苯甲酸甲酯 *為油體(化合物5a)。 一 14 - 本紙張尺度適用中國國家揉準(CNS ) Α4規格(210X297公釐) Α7 Β7 五、發明説明(彳2 ) 啻俐 fi 將化合物1輿等莫耳量的氫氧化納加热•製得N- (6-甲 氧菸鐮醢基)一鄰胺基苯甲酸•熔點224-3。(化合物6) 再將此化合物用氫氧化納處理*製得製得N- (6-甲氧转 齙醣基 鄰胺基笨甲酸納,熔點>250。(化合物6a> 奮俐 7 將勞孫氏試_ (2,4-贰(4-甲氧苯基> -1,3-二_ -2.4-二鼷2.4-二碴化物;5.09克)加於化合物1 (3克 >於四氬呋_ (100毫升)内之溶液中。此混合物於氮氣 下搢拌20小時。再加勞孫氏轼瘌(2.6克)*此混合物於 回流加熱13小時*蒸發,殘餘物於二氧化矽腰柱上作色臛 分析鈍化,製得N- (6 -甲氧基-3-吡啶磓羰基)鄹胺基苯 甲酸甲酯*熔點133-4°。(化合物7> 。 Μ類似前面揭示的實例之一之製法,製得下列式I化合 物0 ----------------、訂------^ (請先閲讀背面之注意事項再填寫本頁) 經濟部中央榡準局*:工消費合作社印製 5 ix 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公嫠) 318829 A7 B7 五、發明説明(15 Y Ο Ν—-G—ί (I) 經濟部中央標準局員工消費合作社印製 化合物 Z Y A 熔點Ο S CCOMe H 5-£^〇-3-啦咱基 150-2 9 — COOEt H 6-Meow 喷基 129-30 10 - coost Me 6 -MeO - 3 -% 喷基 31-2 11 - COOne -CH2CN 6-14£:〇-3_耻0^ 基 oil 12 - COOMe -COOMe 6-MeC-3-吡啶基 gum 13 3-Me cooMe n 6-MeO-3.-B比啶基 111-2 14 5-C1 COOMe K 63 —啦症基 172-3 15 4,5-(MeO)2 COOMe H 6-MeO* 3-¾¾¾ 173-5 16 一 coo苄基 Me 6-Me。-3-¾ 口定基 110-3 17 5-Cl COOMe Me 6-MeO-3-吡啶基 89-91 IS 4 r5-(MeO)2 COOMe Me 6-MeO-3-吡啶基 147-50 19 5-Mes cooMe H 6-MeO-3 胃Pit 喷基 135-7 20 5-MeS COOMe Me 6-1^0-3-¾0¾ 基 78-SO 2_ι CN 6-MeO-3-tft 啶基 163 — δ 22 — CN Me 6-MeO - 3 -啦症基 90,5-3 23 - COMe ΣΙ 6-MSO-3-:吡啶基 131-5-4 24 — N〇2 H 6-MeCX -:¾ 陡基 125-7 25 — COOMe K 5-MeO-2-吡哄基 169-70 26 6-Me c〇〇Me H 6 —ΪΊ©0—3 — 1¾ 1¾ ^ 102.5-5 27 - CCOHe Ή 5-Cl-6-MeO- 165-6 3-吡啶基 16 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X297公釐) I--------:——士衣------ir------&K. (請先閲讀背面之注意事項再填寫本頁) 318829 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明(U ) ib合物 (-)η η Y A 熔點(°) 2δ - CCOMe Me 5-C1-6-Me〇— 3-¾:喷基 110-2 29 6-Me COOMe Me 6 —MeO — 3 — 0¾ B定基 1;Ι7·5_3·5 30 一 COOPrj K 6-HeO-3-吡啶基 :107-9 31 場 COOMe H 6-MeS - 3、0¾ 喃基 102.5-5 32 擊 COOMe Me S-StO-3-耻啶基 oil 33 » CCCMe H 4,6-(MeO)2-5-嘧啶基 125-7 34 - COOMe H 5^6—(M^O)2" 2-吡阱基 156-9 35 Μ COCMe He 3-吡啶基 36-S 36 一 SO-Me II 6-MeO-3-吡啶基 143 * 5-50.5 37 SOMe H 6-Me〇-3-吡啶基 111-3 38 4-NCH COOMe Me 6 —- 3 —耻陡基 110-2 39 - COOH 2-F-苄基 6-Me〇-3-啦喷基 195-7 40 4-MeOCO COCMe Me 6-MeO-2,(ft 啶基 109-12 41 CONH-OMe H 6 —MeO * 3 —眼艇基 152-3 42 - COOMe H 5-(3-唪吩基 )_ 3-吡啶基 149-50 43 一 COOMe Me 6-*NH〇*~3-耻®基 119-22 44 COOMe H S_pr!Ci-3-社啶基 15-7 45 - 四唑. 5_基 -Me 6-MeO-3-败陡基 19S-200 45 — SO^Me He e-MeO-3-Dtti^g 100-2 47 COOMe H S-MeCOO-3“吡啶基 109-12 43 3-C1 COOMe H 6-MeO-3-lft 唯基 106-10 49 COOMe H 4-C1-2-吡啶基 15S-οϋ 50 COOPr H 6_舶〇-3』比咱基: 107-9 51 _ COOBu H 6-贴〇-3-口比唯基 57-60 S2 COOPr Me 6-MeO-3-ft 暗基 81.5-4 53 _ COOBu Me 6-MeO-3-吡啶基 72-6 54 3-C1 COOMe Me 6-MeO-3-吡啶基 S4-7 (請先閱讀背面之注意事項再填寫本頁) -17 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X2.97公釐) 經濟部中央標準局員工消費合作社印製 A7 _____B7 五、發明説明(15 ) 化合物 z Y Λ 瑢點. 55 mm CON-OMe ί Me 6-HeO - 3-口比0^基 147^50 l Mo 56 — CKC H 6-^0-3-¾¾¾ 117-20 57 ·*· COO-allyl u 6 -Μ©0 - 3 - p比陡基 93-5.5 53 4-C1 COOMe 陡基 98-100 59 - COOMe -CK2C=CH 6-MeO-3-耻症基 84*5-87 60 •Η C=N-NHMe I H 6-MeO-3-p^ 喷基 124-34 1 Me 61 C=N-〇Me 1 H 6-Me〇-3-卩比嗤基 115-6 Me 62 4-F COOMe H 6-MeO-3-% 啶基 125-6 63 _ coonh4 H 6-1^^0-3-¾1¾¾ 250-2 64 5,6—本并 COOMe H δ, 157-61 65 4-CF- COOMe H 6-MeO-3-%^S 139-42 66 » COOMe 4_CF3_苄基 6 -MeC- 3 -;Plt ^ ® 111-3 67 — CON-OMe [ K 6-MeO-3-吡啶基 102-4 Me 68 COOMe H 6-MeNH-3-吡啶基 I87-S9 69 - COOMe 2 - Me-苄基 6_贴0-3場?吡啶基 112-4 70 - COOMe 4™MeO一 节基 6-MeO-3 一 基 115-21 71 CONK K 6 -MeO-3 w 1¾ 植基 165-7 CH-7Ph 72 一 COOMe Me 2-吡啶基 3〇-a 73 _ COOMe Η 2-MeO-4-姬旋基. 132-5 74 邏 COOMe Η 5,6-012-3-¾ 陡基 161-2 75 — COO- N 十 Bu4 H 6-MeO-3-吡啶基 250-2 76 . · COOMe Η 2-C1-3- ’耻陡基 120-1 77 COOMe Η 2 -MeO- 3 —阳:陡基 7S-S1 -18 - (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家檬準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明(16) 化合物⑺Μη 2 經濟部中央標準局屬工消費合作社印製 78 - CKO Me 6-Meo-3 - 0比陡基: 83-4 79 - CH=N-〇H h 咱基 145-6 80 - I * H 6_5^0_3_啦啶基— 87-9 1 Me 81 - I H 嗤基. 140-2 82 - COOMe H 2-MCS-3-吡啶基. 117-9 83 - COOMe 5-Br-6-MeO~ 164-3 3-吡啶基, 34 - COCNe Me 5—Br-^ —MeO ^ 112-4 3-毗啶基 3 5 — COGMc H 5-ΜθΟ-2 基 141-3 36 - COO^ie H 6*-Μθ-3 -基 125-6 37 5-Me COOMe H 2-MeO-3-吡啶基 13S-40 33 - COOCjH^ K 6-MeO-3-¾¾ 基 4S-52 S3 — CC〇Cr〇- H 6-MeO-3_.吡啶基 125-7 COOMe 90 ~ COOCK-j- H 6-MeO«3-〇lt〇£S 129-32 91 — COOBu1 H 6 -MeCW 3 - % 哺基. S1-3 32 _ COOHe H 5-Ph-6-Mc〇- 159-61 3 -啦腔基、 93 - COOKe -CII: ?C〇OHe 6-MeO-3-基 oil 94 * cootoenzyl .H 2-MeO-3—% 症基 79-30 95 ~ CONKHe H 6 - - Oft 陡基, 162-4 96 - C—N-OMe 1 MO 6-MGO-3-吡啶基: oil 1 Me 97 - Ph H 6-^6〇-3-:0比°^基: 107-9 - 5-(4-Cl- H 6 -MeG - 3 "眼喷基 193-7 Ph)-i,3,4- 二啤-2-基 (請先閱讀背面之注意事項再填寫本頁) -19 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) A7 B7 五、發明説明(17)
化合物(RA)n Z 99 - 100 4-F^S-Me 101 -102 - 103 ^
104 5-F 105 - 10 6 -107 -* 102 - 109 一 110 - 111 -112 - 113 - 114 - 115 — llo 4-He 117 一 IIS - 119 5-Me 120 -121 G-Cl
A 經濟部中央標準局員工消費合作社印装 環己基 COO· Ν + Η] H S-MeO-O-吡啶基.. 203-5 環己基. COOMe Η 2-MeO—3 —阳;0¾ 基. glass 2-furyl H 6-MeO-3-吡啶基. 112-7 cooch2- K 6-MeO-3-吡啶基 155-δ CK-,G1 cookie Me ,2—MeO-3-耻喷基 oil COCHe H 6-MeO-3·% 晚基 125-6 COOMe 稀丙基 oil COOMe 乙醯基 色 3 -1¾唯基 oil COOMe 苯甲醯基 6-14^0-3-¾¾¾ 117-S COOMe 3,4~Ήβ〇2" 6-MeO-3·吡啶基‘ 116-8 COOMe ph.—CH-sCH.^ -Η 5 eO— 3 _ (¾ D定基 117-9 COOMe -CH2Ph S-Cl-6—Me〇- 126-8 COOMe Me 3-吡啶基‘ 5,S-Cl2-3-吡啶基.. 103-4 COOMe II 5—C1 — 6 —M©S — 167-9 COOMe K 3-吡啶基 比啼基 122-3 5-(4-CI- Me 6-MeO-3 - Pfci:喷基 13S-91 Ph)-1,2,4-晖二唑-2-基 COCM^ Μβ 4,6-(ΜβΟ)2" 111-3 COOMe H 2-嘧啶基. 6-MeO-3-'卩比η定基 116-9 COOMe Me 5_MeO—2 — 基 ^ 82*4 SO^NHMe u 6-MeO-3-®:喃基 sclid COOMe H 6_Me〇-3 -ift嗤基 丄 5G-2 COOM^ Mg 5—Me〇一 3 一 Ptti® 基 ¢0-2 COOMe K 6-Me〇-3-吡啶基 160-2 -------Γ--------ίτ------良 (請先閲讀背面之注意事項再填寫本頁) 20 本紙張尺度適用中國國家標準 (CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 __B7 五、發明説明(18 ) 化合物 (Rl)n Z V A 熔點.(3) 122 cc〇Me H 5,6_(MeO)2_ 3-吡啶基 155-7 123 一 5-(4-01-PhJ-1,3,4-_二唑-2-基 H 6-ile〇-3-吡啶基 215-7 124 - C0NH COOMe H 6-MeO-3-1¾ 嗤基 140-2 125 4-C1 COOMe H 2-(MeS〇2)" 啶基 183-5 126 5-NO, •COOMe K 6-ΜβΟ-3 -啦唯基 197-9 127 3,5-Me? C00MC H 咱基: 131-3 123 - COOMe SO舞 6-Μθ:0·3 -啦陡基 125-8 129 - COOHe II 4 —Hg〇"~2 — MsSO·^ w 5-啼陡基 lS7_9〇 130 i·吡咯基 H 5-Me〇-3-Dtt 唯基 113-6 131 4—Cl COOMe H 剛定基 175-7 132 cooMe H S-Me〇-3-吡啶基 177-9 133 4-MeO COOMe H 6-Mg〇-3 -啦嗦基 164-5 134 — COOMC -CH(M$)Ph 6 '"MoO- 3 _ 〇H: 1¾ 基 132-3 135 - COOMe Me 5/6-(ΜβΟ)2" 3-吡啶基. 110-2 136 一 C〇CH?0Me H 6-MeO-3-吡啶基: 110-2 137 - CONH, H 6-MeO-姬陡基< 224-S 138 一 COOMe H 4· wCl-6 —〔N_ (2—MeOCO— Ph)HHCO]-2* 吡啶基. 210-2 139 CCOMe H 4—McO—β— [ N— (2 -M.eO— CO-Pii)NHCO]-2-吡啶基 195-9 140 - COOMe H 6-[N-(2-Me〇CO-Ph)-NFCO] -3*·阳:唯基 198-200 141 一 COOMe H 6-CF3CH2〇-3-吡啶基. 173-4 (請先閱讀背面之注意事項再填寫本頁) -21 - 本紙張尺度適用中國國家標準(CNS ) A4規格(2IOX297公釐) A7 經濟部中央標準局員工消費合作社印製 318829 B7 五、發明説明(19 ) 化合物(ν)η 2 Y A 诏點.(。 142 替 co〇Me H 2,5-(MeO)2_6-[N— (2 -MeOCD-Ptl) NHCO ] ^ 3-%¾基 195-9 143 麵 COOHe 4,6-(EtO)2-2-吡啶基 115-6 144 - C〇NEt2 H 6-Me〇-3-吡啶基 oil 145 conhnh2 K 6-Me〇-3-吡啶基 183-9 145 - CONH- N=CMe2 H 6-Me〇-3-吡啶基 174-7 147 - COOM 白 2-Me-苄基 2-MeO-3-吡啶基.. 101-3 14S ?-νη2 COOMe H 6-MeO-3-吡啶基 171-3 149 - COOMe H 6-(2,3, pyrrol.yl〉*-3-吼喃基 1S3 150 — SCH〇CH?CN !l 0 l·: S-MeO-3-吡啶基 113-5 151 2-benz— R imidasolyl o 6 —M eQ—3 - 1】比P定基 272—5 152 - li SCH^CH-^CN il 0 H 6-MeO-3-吡啶基. I41-3 153 COMHNH- COMe H 6 一 Me〇一 3 參 1¾ 0¾ 基 193-7 154 一 C〇〇-ally丄 H 5-Cl-6-MeO-3-吡啶基 113-5 155 — COOCHo- C^CH H 5-Cl-6-MeO- 3-吡啶基. 10 3 — 5 156 3-F CCOMe u 6 -MeO — 3 _口比 基 107-9 157 5-ΟΗ co〇Me H 6-MeO-3-吡啶基 203-5 15S 5-1 CCOMe H (3-Me〇-3-吡啶基 154—0 159 5-Me〇C〇 COOMe H 6-MeO-3-pttng 基 155—β (請先閲讀背面之注意事項再填寫本頁) -22 -本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A 7 __B7 五、發明説明(20 ) 化合物(R1)^ Z Y 熔點(3) 160 5-MeCONH COOMe H 2S2-6 161 - GOOMe -CH(Me)-COCHe 6-MeO-3-吡啶基· 134-5 152 - COCMc 节基 5-Cl-6-MeO-3-吡啶基. oil 163 — COOEt H 5-Cl-6-MeO-3-吡啶基. 136-3 164 - COOH H 5-Cl-6-Me0-3'- Ptt 喃基_ 247-50 165 5-MSSO-7NH .COOMe H 6〜ΜβΟ-3-败症基 184-5 1S6 C00M° H 5-氣基:-3-¾咱基_ ISC*2 167 COOiMe H 卜甲酿基-3-¾啼基 153-7 16S CONH- (4-Cl»Ph) H 6-HeO-3-D(£D$g ias-90 159 - COOMe K 5-3r-2-Me〇-3-吡啶基 180-2 17C 4-Cl cooKe Me 2-MeO-5-暗症基 S 6 —δ 171 COOMe H 2-01-4-¾ 暗基 10S-1C 172 一 COOMe H 2- G1-6-MOO- 3- 吡啶基 144-5 173 - COOHe H 6-(2r3f4,5-Cl4-1-¾略基-)-3-吼陡基 2S9 174 _ COONa H 6-C1-3-PH:咱基. 300 175 一 COOMe H 6-MeOCH,-3-% 啶基 117-8 176 - COOMe H 5-氮基 3-吡啶基 247-50 177 - 5-Me-1,3,4-噻二唑-2-基 H β—M©〇—3 — 〇比唯基 143-5 173 - COOM^ H 3-吡啶基. iy〇-2 179 — COOMe H 5—MeSO,〇—3 _眼旋基. 149-51 (請先閲讀背面之注意事項再填寫本頁) -23 麵 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 318329 Α7 Β7 五、發明説明(21 ) 化台物 熔點(°)
130 - COOMe H 181 - COGMe H 132 - COOHe H 133 - COOKe H 184 - COOHe II 185 - COOHe H 18 6 - CCOHe H 1S7 - cocHe H 183 * COOMe Me 1S9 - COOMe H 19 0 · CCCMe Me 191 - COOMe H 192 一 C00H ti 193 - COOMe Π 194 - COOHe H 19 5 - COOHe H 196 - COOMe H 197 - cooHe H 19S - COOMe H 199 - -CO-COOMe II 200 - COCMe He 201 - C〇〇Me Me 202 _ CCOMe He 203 - COOH H 6-(2,3,5-CI3- 134-5 卜吡咯基 )-3-吡啶基 6-MeOCO_3_ 耻1® 基 141 5-P定基. 123-31 5 —He £—3 — ft 0¾ S. 122-3 5-MeOCO-2-吡啶基. 1S7_S 2 f 6- (MeO) 2** 141-3 3-吡啶基 5--社啼基_ 155-70 5-MeS〇-3 -ρ%1® S' 120-2 基 oil (N^C—CH-^O)— so?Lid 3-吡啶基 5—HcSO〇"3 —社啼基 109-11 5-C lCIi2S - 3 -毗啶基· 6-C1-3- Ptt1® ®, 240 5->MeOCO-3 -附‘啶基 14 7-3 6-[N-(2-HeOCO-Ph)- 195-9 KHCO 陡基 5 - Me-3 -pi% 唯基 116-7 NO7— 15 0—1 3-吡啶基, 6-Ph〇-3- 'ftBiS, 97-s 5 f (MeS) 2* 157—8 3—吡啶基 6-KeO“3-耻症基 13 3-6 2 f 6- (HeO>2^ 103-5 3-吡啶基. Pth^E® oil 5-Me-3-吡啶基. 114-5 5 -aoco- 3 啶基 275 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印策 _ 24 — 本紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ297公釐) 五、發明説明(22 ) A7 B7 經濟部中央標準局員工消費合作社印製 化合物(R1、 z Y A 熔點(°) 204 - COOMe H S-乙醯基-S-Me- 3-吡啶基 144-5 205 - COOMG H 5-Ph-3- 〇tt 唯基: 12A-5 206 - COOMe Me 6-PhO-3-吡啶基i 114-5 207 - COOMe H 5**[N-(2-Me0C0-Ph)-NHC0 ;] - 3 -耻 _ 硫基 180-2 202 - cooMe H S-phCH^jS-S-吡啶基 104-6 209 - cooMe Me 5 - MeO-2-W:畊基 81-3 210 4-? COOHe Me 6 - % 症基 102-4 211 - COOMfit Et 6-Me〇-3-Pft 啶基. 53-5 212 - COOMe H 2-Me〇-5-喷症基 164-S 213 - COOMe Me 2-Me〇-5"嘧B定基. 125-30 214 - COOMe H 4, 6-(MeO)2_2-PhCH2〇- 5-嘧啶基 127-$ 215 - cooMe H 2-C1-4C?:'-5-嘧啶基 139-40 2 IS - COOMe H 2-Me-;N-4CF3-5-嘧啶基 133-6 217 - COOMe H 2-MeO-4CF3™ 5-嘧啶基: 13940 21S · COOMe H 6-Cl-5-MeO-2-〇ttn井基 163-71 219 - COCMe H 5-Br-2-Me- 4-嘧啶基 165-6 220 - COOMe H 2,4,6-(MeO)3-5-嘧啶基 153-5 221 » COOMe He 6β1-3-吡啶基. 8 4 — 6 222 - COOMe H 2-C1-4-嘧啶基 159-61 223 - COOTie 5-Me-2-吡畊基 224 一 c〇GMe H 2-MeO-4 -喃唯基 135-6 225 - co〇Pr H 2 -HeSO-7— 5-嗯喃基 — 129-31 —25 — 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X 297公漦) -----------i衣-- (請先閱讀背面之注意事項再填寫本頁) ,ιτ 經濟部中央標準局員工消費合作社印製 318829 A7 B7 五、發明説明(25 ) 226 - COOPr H 2-MeSO- 5-嘧啶基 116-3 227 - COOPr H 2-Me〇-5-嘧啶基,. 1U4-5 228 - COOEt H 2WtO-5-啼陡基. 134-5 229 - COOH H 2-Et〇-5-嘧啶基 150*62 230 - COOMe H 2-Me-5-p:啼唯基 141 — 3 231 - coOMe H 5-嘧啶基 15S-61 232 · co〇Me Me 2-Me-5-嘧啶基. 83-90 233 - COOMe U 2-C1-5—嘧啶基 _ 159-61 234 - COOHe H 2-Br-5-嘧啶基 177—3 2 J 5 - 'COOMe H 2-PhCH2NH-5-嘧啶基 192-4 236 一 COOMe H 2-嗎福啉基 5-〇g症基 222-3 237 - COOMe K 5-Br-2-MeS- 嘧啶基 192-4 23S - cooMe H 4-嘧啶基 178-30 239 - COOMft H 2-MeCC〇CH2NH-5-嘧啶基 194-7 240 - cooMe H 2 , δ-ΟΙο"* 4-嘧啶基 170-5 241 - C00MO H 2-CF3**5-暗啶基. 143-5 242 - COOMg H 2-Ph*5-赠啼基, .151-5 243 - COOMq H 2,6-(MeO)2" 4-嘧啶基 167—9 244 - COOMe Me 2-Ph-5-嘧啶基 gura 245 - COOMe H 2; 6-Cl2~ 5-嘧啶基 135-7 246 - COOMe H 2-NC-5-嘧啶基 136-3 247 - COCMc H 4,5- (MeO) 2" 2-嘧啶基 1S2-3 (請先閱讀背面之注意事項再填寫本頁) * 26 -本紙張尺度適用中國國家梂準(CNS ) A4规格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A7 __B7 五、發明説明(24 ) 化合物(w)n 2 V A ‘熔點(。) 243 - COOMe H 4/6-(MeO)2-2-嘧啶基 163 — 4 249 - CCOMe H 2-MeONK-5-嘧啶基 19 4 — β 250 - COOMe H 5-嘧啶基 230-1 251 - COOMe H 2-CI-4-(2-MeOCO-PMH) - 5-嘧啶基 190-2 252 - COOMe 5-Ci-6wMe-2-吡畊基 136-41 2B3 - 'COOMe K 5-HeO-5-Me_ 2-吡畊基 16 6 — 9 254 — COOMe u 2-(N-甲氧基 一 N#甲氧猿基 _ 胺基 )-5-嘧啶基 151-2 255 COOlie K 2-環丙基 S--嘧啶基. 112-^ 256 3-MeOCO COOMe u 6 _MeO - 3 — 口比喷基 111-4 257 COOMe H 2-MeS-5-嘧啶基 160-2 25S 一 COOMe H 5,2-阳:哄基 143-S 259 - COOMe H 5-(2-_噻吩基)-3-吡啶基_ 143-9 260 - COOMe H 5-(i-CF3-Ph)-3-吡啶基: 155-6 261 — COOMe H 5-(ClS〇2)-3-吡啶基. 144-3 252 - COOMe H 5-(CL2CHS)» 3-吡啶基 120-2 263 COOMe H 5-(NH2S〇2) -3-吡啶基. 135-7 264 COOMe H 5-Br-6-Cl~3- 157-9 265 - COOMe He 5 - NO。一 6—MeO-3-吡啶基 9S-100 I----------1¾衣------?τ------ (請先閲讀背面之注意事項再填寫本頁) -27 - 本紙張尺度適用中國國家標準(CNS ) A4規格(2IOX297公釐) 318S29 A7 B7 五、發明説明(25 經濟部中央標準局員工消費合作社印製 化合物(y)n 2 V A 熔點(5) 256 辦 COCHe K 2-(l-眯唑基 Ιό-嘧啶基 193-5 267 _ COOMe H 4 ♦HeO-2—MeS·"-5-喑啶基 140-2 258 — COOMe Me 2 f 6- (Me〇) 啤婉基 101-3 269 情 COOH 3, r 4-(HeO)2" 苄基 社啼基 123-4 . 270 — COOMe H 5-(Me?NS〇2 卜 3 - 旋基 169—70_ 271 — COOMe H 5-Br—S^MeO— 3-基. 169-70 272 一 COOMG H 5—6—MgS〇7_ 3-吡啶基 223-5 273 - COOMe H 5—Sr—6.SC— 3-吡啶基. 160-2 274 — cooc5hu H 2-MeO-3-吡歧基 47-3 275 — COO-ally1 H 2-ΜβΟ-3-ϋίΡ定基. 80-1 276 - COOMe 2-Me-苄基 6-(2-Me-节基.)- 3-吡啶基 oil 277 一 COOMo H 2-C1-4-B奎睹咐基 163^4 27S 一 COOMe -CH2Ph 6-MeO-3-吡啶基 101-2 279 4,5-Me〇2 COOMe H 2-MeO~3-tft啶基: 152-4 2S0 COOMe n 5 —WH^ ^ 6 -Μβ〇·* 3-吡啶基. 202-3 231 — COOHe He 2,4- (MeO) 2" 5-嘧啶基 7S-S1 282 - COOMe 2-MeO-苄基喃症基 gum 233 COCMc 4-Me-2-MeS-' 78-Sl 5-嘧啶基 28 良紙張尺度適用中國國家橾準(CNS ) A4規格(210X297公釐) (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 318329 A7 A7 B7 五、發明説明(26 ) 化合物(R1):! S Y A 熔點(°) 234 - COOMe H 2-(3-:¾咱氧基 )- l2d~6 5-嘧啶基. 2S5 * COOMe H 2-F-3-吡啶基 130-1 236 - COCMe 2 — S,6-(MeO)2- oil benzyl 3-吡啶基 2S7 - COCKe H 5 , S-伸甲基二氧基 w 168—79 3-吡啶基 233 _ COOMe H 5 -1 - 6 -MeO-卩比症基 173-5 289 3,4-Me2 COOM0 H 2 -MeO - 3 -卩tfc卩定基. 126-7 290 4-C1 COOMe H 2-MeO-3-吡陡基 128-30 -------:--------.訂------2 I (請先閲讀背面之注意事項再頊寫本頁) -29 - 本紙張尺度適用中國國家揉準(CNS ) A4^格(210X297公釐) 經濟部中央標準局員工消費合作社印製 A7 _____B7 五、發明説明(2?) 也製備了下述化合物: a>H- (6 -甲氧基-3-吡啶硪代炭基)鄰胺基苯甲酸乙_ * 為油體,(化合物291 ) b>N- (5,6-二甲氧基-3-吡啶碕代炭基)鄰胺基苯甲酸甲 酯,熔點154-5。,(化合物292 ) c>H- <2-甲氧基-5-嘧啶硫代炭基 > 鄰胺基笨甲酸甲酿, 熔點135-7。,<化合物293 >,及 d)N- <6-甲氧基-3-吡啶硫代炭基)鄰胺基苯甲酸異丁 _ ,為油體·(化合物294 >。 試驗奮例 評估各化合物對下列一或多種疾病之活性: P h y t 〇 p h t h o r a i n f e s t a n s :晩期蕃 S5 疫病 Plasaiopara viticola:葡萄霜霉病 Erysiphe graminis··大麥白粉病 Pyr丨cular丨a oryzae:招瘟病 Pellicularia sasakii:稻销疫病 B o t r y t i s c i n e r e a :灰霉病 V e n t u r i a ί n a e q u a 1 i s :顔果瘡痛病 Leptosphaeria nodorua:類斑病 M此等化合物所懦湄度的水溶液或分散液•包括增獮薄 *噴或浸於試驗植物的莖下部。然後將植物或植物的一部 分以合逋的試驗病原菌培養•使植物在受控制的條件下生 -30 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) I I I I— fA (請先閣讀背面之注意事項再填寫本頁)
第84102Γ)27號專利申請案 中文說明書修正頁(86年1月 五、發明説明( ----------裝—I----訂 (請先閱讀背面之注意事項再填寫本頁) 長,Μ便植物及病原菌都能發育。過一段合適的時間後* 肉眼估許植物感染部位的程度。評估真菌病害之控制程度 W分數0-4表示,其中各代表之意義如下: 〇= 0-24% 控制 1 = 25-49¾ 控制 2 = 50-74% 控制 3 = 75-98¾ 控制 4= 99-1003;控制 在化合物濃度為500 ppm (重量/容積)或更少時如分數 為2或2M上,即認為化合物對該疾病有活性。 於濃度500 ppm或更少: 化合物 30, 36, 43, 47, 58, 112, 115, 180, 242,及 289 之分數為 2或 2M 上 Μ 抗 Phytophthora infestans; 化合物 9, 30, 36, 40, 42, 57, 58, 59, 62, 63, 67-70. 76, 77, 82, 83, 96, 112, 115, 127, 129, 130, 132, 138, 139, 161, 163, 166, 181, 186, 200-204, 210, 213, 234, 248, 249, 261, 267, 268, 經濟部中央標準局員工消費合作社印製 271,及 2*77 之分數為 2 或 2M 上 Μ抗 Plasmopara viticola • 化合物 1-3,9-12,20, 23,25, 27-29,32, 33,34, 38, 39, 41, 46, 50, 52, 62, 66, 70, 73, 83, 84, 90, 91, 104-104, 110, 113, 115, 121-123, 132, 135, 145, 154, 155, 163, 176, 177, 196, 200, 208, -31 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐)
81妁 中文說明書修正頁(86年1月)T 02527號專利申謫案 A7 子月 3
Wi-i補充j 五、發明説明(Y) 209, 210-2, 213, 218, 228, 239, 243, 249, 150, 252-4, 258, 265, 268, 271-3, 275, 276, 278,及 286 之分數為2或2M上K抗Erysiphe graminis ; 化合物 1, la, 2, 6a, 48, 29, 54-56, 65,68, 72. 74, 75, 126, 129, 145, 146, 169, 171, 197, 230, 23 2,249,及 277 之分數為 2或 2K 上 Μ抗 Pyricularia 〇 r y z a e ; 化合物 14, 44, 49, 62, 1 14, 1 15 , 152, 21 1, 215, 216,及278之分數為2或2K上K抗Pellicularia sasaki i ; 化合物 48, 51, 52, 53, 61, 63, 1 21,129,195, 228 及 251 之分數為 2或 2M 上 Μ 抗 Botrytis cinerea; 化合物 1, 8, 12, 17, 45, 63, 86, 104, 112, 119, 146, 149, 150, 151, 187, 204, 211, 219, 224, 239, 244,245, 248,及250之分數為2或2M上以抗Venturia i n a e q u a 1 is ; 化合物 24, 35, 60, 61, 71, 204, 216, 220,及 249 之 分數為 2或 2M 上 M 抗 Leptosphaeria nodorum 。 ^^1-^^^1 m nn m m· m * 1^^1- 1^1^9J (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標隼局員工消費合作社印製 32 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐)
Claims (1)
- 第84102527號專利申請案 丨專利範圍條正太(86年1月) A8 . B8 ' 六、申請專利範圍 .一種式I之化合物 (R1) XN—C—A. (I) 其中 X是 A是 R1是 R2是 經濟部中央標準局員工消費合作社印製 0或S ; 吡啶基,吡阱基或嘧啶基,視需要可被一或多個 1?2基團取代; Cl-4综基,Cl-4齒fes基* Cl-Λ综氧基* Cl-4·院硫 基,咹基,酵烷基,(:烷磺醯胺基,鹵素 ,羥基,硝基,烷氧羥基,或二個相鄰的基 團與其相聯的碳原子共同形成茏并環; Cx-4烷氧基* Ck烷基,C!—鹵烷基,Ci-4烷氧 _Cl-4综基> Cl-4®烧氧基,Cl-a综硫基,Cl-4 鹵烷碲基,吡啶硫基,吡啶氧基,鹵吡咯基, (Ca-4烷氧羰茏基)胺羰基,Cx-4烷氧羰基, 烷氧羰-Ct-a烷胺基*苄氧基,嗎福啉基, 氟基,烷氧基•胺基,Ci-4烷胺基,C:L-4烷 氢睽基,N - C i - <1烷氧-N - C 1 - 4烷羰胺基,C i - 4醇 基,氧基,Ci-4烷碣臨·氧基,Ct-4烷磺醯 基’ Cl - 4综亞碌藤基,商素,哮吩基,硝基,梭 * /碏醻胺撐,N.N-Ci-A二烷磺藤胺撐,眯唑基 n^n ^1^11 HH «^—^1 n* fti^i— nil— ^mfl 1J 、va (請先閏讀背面之注意事-^再填寫本頁) 本纸張尺度速用中國國家標準(CNS ) A4洗格(210X297公釐) 31S829 公告‘本 A8ΰά -DS、 經濟部中央標準局員工消費合作社印製 申請專利範圍 ,或二個相鄰的基團與其相聯的碳原子共同形成 茏并或亞甲基二氧基; Y是 氫,C Λ - Λ烷基(:視需要羥氰基取代1,C t - 4烷氧羰 基,C2-4炔基,苄基(視裔要羥鹵素或Cl-4烷基 ,鹵-CP4烷基或烷氧基取代),醇基, 笮氧基*笼乙基,Ca-4 -烷磺醯基或α-甲基苄基 » Ζ是 氟基,硝基,Ci-4醇基(視需要經烷氧基取代), C 1 - a -烷磺酵基(視需要經氰基取代),c i 4烷亞 磺醯基(視需要羥氰基取代),Ci-4垸磺醯胺撐, Crt-d-垸氧羰基,或選自四唑基,晖二唑(視需要 涇鹵呆基取代),噻二唑基(視需要羥鹵苯基或 C- 4垸基取代),呋喃基,吡咯基或茏并眯唑基 ,或基團COOR3,其中烷基(視需要經茏 基,Cl-4L综氧截基或鹵素),Cz-Λ -烯基,C2-4块 基,茏基,氫或一無機或有機陽離子基團; 或基薄!-CiRs)=N-R3;其中R5是氫,Ct-4垸基及 Re是羥基,C^-4 -二烷胺基或Ct-4烷氧基,或基 團-CONR7R8,其中R7是氫,烷基,R8是氫, Ck烷氧基,C^-4烷基,胺基,(:τ-4酵胺基, C,-4烷氧羰基,苄基,Ct-4-烷亞胺基或鹵苯基 η是 0,1或2 ; 及與金覉鹽形成的錯合物,以及與鹼所成的鹽(當化合 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) n 1n^ ntn 1^1 —Bui V^ ^mn Inti n (請先閲讀背面之注意事項再填寫本頁) 3iS8% 4 本 A8 B8 C8 D8 年Λ β 補充 申請專利範圍 2 . 3 . 物為酸)及與酸所成的鹽(當化合物為鹼),前題是在 Y為氫旦 i ) z為羧基,甲氧羰基或乙氧羰基時,環A並非未經 取代的吡啶基或吡哄基;而 y ii)在z為羧基且η是0時,ί\不是2 -氯-4-吡啶基, 6- (2 -二乙胺乙氧基)-3-吡啶基或2 -吡啶基。 一種殺真菌姐合物,其含有與展業上可接受的稀釋劑或 截體摻和的根據申請專利範圍第1項之化合物。 一種於植物感染部位或可能感染部位克服植物病原性真 菌的方法,其包括於該部位使用根據申請專利範圍第1 頂之化合物。 1 — n HI —i— n ft - l m ____ In - m T ·ν5 (請先閲讀背面之注意事1再填寫本頁) 經濟部中央標隼局員工消費合作社印製 本紙張尺度逋用中國國家橾準(CNS ) Α4规格(210Χ297公釐)
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GB9405347A GB9405347D0 (en) | 1994-03-18 | 1994-03-18 | Fungicides |
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EP (1) | EP0750611B1 (zh) |
JP (1) | JPH09510471A (zh) |
CN (1) | CN1143954A (zh) |
AT (1) | ATE168099T1 (zh) |
AU (1) | AU688473B2 (zh) |
BR (1) | BR9507105A (zh) |
CZ (1) | CZ269096A3 (zh) |
DE (1) | DE69503365T2 (zh) |
GB (1) | GB9405347D0 (zh) |
HU (1) | HU214292B (zh) |
IL (1) | IL113027A0 (zh) |
PL (1) | PL316289A1 (zh) |
TW (1) | TW318829B (zh) |
WO (1) | WO1995025723A1 (zh) |
ZA (1) | ZA952205B (zh) |
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DE2417216A1 (de) | 1974-04-09 | 1975-11-06 | Basf Ag | Fungizide |
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1994
- 1994-03-18 GB GB9405347A patent/GB9405347D0/en active Pending
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1995
- 1995-03-16 TW TW084102527A patent/TW318829B/zh active
- 1995-03-16 PL PL95316289A patent/PL316289A1/xx unknown
- 1995-03-16 JP JP7524455A patent/JPH09510471A/ja active Pending
- 1995-03-16 WO PCT/GB1995/000570 patent/WO1995025723A1/en not_active Application Discontinuation
- 1995-03-16 US US08/714,149 patent/US5756524A/en not_active Expired - Fee Related
- 1995-03-16 AT AT95911403T patent/ATE168099T1/de active
- 1995-03-16 EP EP95911403A patent/EP0750611B1/en not_active Expired - Lifetime
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- 1995-03-16 DE DE69503365T patent/DE69503365T2/de not_active Expired - Lifetime
- 1995-03-16 AU AU18981/95A patent/AU688473B2/en not_active Ceased
- 1995-03-16 HU HU9602547A patent/HU214292B/hu not_active IP Right Cessation
- 1995-03-16 BR BR9507105A patent/BR9507105A/pt not_active Application Discontinuation
- 1995-03-16 CZ CZ962690A patent/CZ269096A3/cs unknown
- 1995-03-17 ZA ZA952205A patent/ZA952205B/xx unknown
- 1995-03-17 IL IL11302795A patent/IL113027A0/xx unknown
Also Published As
Publication number | Publication date |
---|---|
HU214292B (hu) | 1998-03-02 |
AU688473B2 (en) | 1998-03-12 |
WO1995025723A1 (en) | 1995-09-28 |
ZA952205B (en) | 1995-10-31 |
AU1898195A (en) | 1995-10-09 |
HU9602547D0 (en) | 1996-11-28 |
IL113027A0 (en) | 1995-06-29 |
CZ269096A3 (en) | 1996-12-11 |
BR9507105A (pt) | 1997-09-09 |
US5756524A (en) | 1998-05-26 |
CN1143954A (zh) | 1997-02-26 |
JPH09510471A (ja) | 1997-10-21 |
EP0750611B1 (en) | 1998-07-08 |
ATE168099T1 (de) | 1998-07-15 |
DE69503365D1 (de) | 1998-08-13 |
MX9603735A (es) | 1997-12-31 |
DE69503365T2 (de) | 1999-01-07 |
PL316289A1 (en) | 1997-01-06 |
GB9405347D0 (en) | 1994-05-04 |
EP0750611A1 (en) | 1997-01-02 |
HUT74778A (en) | 1997-02-28 |
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