KR19990028230A - 살절지동물성 및 살진균성 시클릭 아미드 - Google Patents
살절지동물성 및 살진균성 시클릭 아미드 Download PDFInfo
- Publication number
- KR19990028230A KR19990028230A KR1019970709541A KR19970709541A KR19990028230A KR 19990028230 A KR19990028230 A KR 19990028230A KR 1019970709541 A KR1019970709541 A KR 1019970709541A KR 19970709541 A KR19970709541 A KR 19970709541A KR 19990028230 A KR19990028230 A KR 19990028230A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- chr
- haloalkyl
- alkoxy
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 230000000855 fungicidal effect Effects 0.000 title claims description 11
- 150000003950 cyclic amides Chemical class 0.000 title description 3
- -1 C 2 -C 6 Haloalkynyl Chemical group 0.000 claims abstract description 517
- 150000001875 compounds Chemical class 0.000 claims abstract description 428
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 128
- 150000002367 halogens Chemical class 0.000 claims abstract description 127
- 239000000203 mixture Substances 0.000 claims abstract description 92
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 89
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 82
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 80
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 79
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 78
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 77
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 74
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims abstract description 72
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 51
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 43
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 17
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 15
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 7
- 238000007667 floating Methods 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 138
- 238000000034 method Methods 0.000 claims description 89
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 80
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 69
- 239000007787 solid Substances 0.000 claims description 57
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 40
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 33
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 30
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 29
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 29
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 23
- 241000238421 Arthropoda Species 0.000 claims description 23
- 239000003085 diluting agent Substances 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 22
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 17
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 229910018540 Si C Inorganic materials 0.000 claims description 14
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 239000012071 phase Substances 0.000 claims description 13
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 230000009969 flowable effect Effects 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 6
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 239000007790 solid phase Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 claims description 4
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 3
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000003828 azulenyl group Chemical group 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- XTBBNHNLZSAXIZ-UHFFFAOYSA-N 4-[2-[[3-(3-ethynylphenyl)-1,2,4-thiadiazol-5-yl]oxy]phenyl]-5-methoxy-2-methyl-1,2,4-triazol-3-one Chemical compound COC1=NN(C)C(=O)N1C1=CC=CC=C1OC1=NC(C=2C=C(C=CC=2)C#C)=NS1 XTBBNHNLZSAXIZ-UHFFFAOYSA-N 0.000 claims 1
- 244000000005 bacterial plant pathogen Species 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 47
- 239000000417 fungicide Substances 0.000 abstract description 25
- 239000004480 active ingredient Substances 0.000 abstract description 12
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- 239000000543 intermediate Substances 0.000 abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 90
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 85
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 45
- 229940093499 ethyl acetate Drugs 0.000 description 44
- 235000019439 ethyl acetate Nutrition 0.000 description 44
- 238000012360 testing method Methods 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- 229920006395 saturated elastomer Polymers 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 241000196324 Embryophyta Species 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- 239000012044 organic layer Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- 239000003153 chemical reaction reagent Substances 0.000 description 20
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 241000607479 Yersinia pestis Species 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 239000011780 sodium chloride Substances 0.000 description 15
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229960004397 cyclophosphamide Drugs 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000005767 Epoxiconazole Substances 0.000 description 10
- 241000238631 Hexapoda Species 0.000 description 10
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 229960000485 methotrexate Drugs 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- 239000012038 nucleophile Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 150000001728 carbonyl compounds Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- 241000238876 Acari Species 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- 239000005839 Tebuconazole Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 231100000676 disease causative agent Toxicity 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 244000052769 pathogen Species 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- 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
- A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N43/82—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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34195P | 1995-06-20 | 1995-06-20 | |
| US60/000341 | 1995-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR19990028230A true KR19990028230A (ko) | 1999-04-15 |
Family
ID=21691089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019970709541A Withdrawn KR19990028230A (ko) | 1995-06-20 | 1996-06-13 | 살절지동물성 및 살진균성 시클릭 아미드 |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0836384A1 (cs) |
| JP (1) | JPH11508257A (cs) |
| KR (1) | KR19990028230A (cs) |
| AU (1) | AU6177096A (cs) |
| BR (1) | BR9609001A (cs) |
| CZ (1) | CZ394097A3 (cs) |
| HU (1) | HUP9901228A3 (cs) |
| IL (1) | IL122670A0 (cs) |
| MX (1) | MX9710259A (cs) |
| NZ (1) | NZ310884A (cs) |
| PL (1) | PL324291A1 (cs) |
| WO (1) | WO1997000612A1 (cs) |
| ZA (1) | ZA965196B (cs) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9615831D0 (en) * | 1996-07-27 | 1996-09-11 | Agrevo Uk Ltd | Fungicides |
| JP2000516583A (ja) * | 1996-08-01 | 2000-12-12 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 殺節足動物性および殺菌・殺カビ性の環状アミド類 |
| AU4660397A (en) * | 1996-11-01 | 1998-05-29 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
| WO1998023156A1 (en) * | 1996-11-26 | 1998-06-04 | E.I. Du Pont De Nemours And Company | Methyl substituted fungicides and arthropodicides |
| AU6040398A (en) * | 1997-01-30 | 1998-08-25 | E.I. Du Pont De Nemours And Company | Fungicidal compositions |
| ZA9711323B (en) * | 1997-01-30 | 1999-06-17 | I E Du Pont De Nemours And Com | Fungicidal mixtures |
| EP1310169A3 (en) * | 1997-01-30 | 2003-08-27 | E.I. Du Pont De Nemours And Company | Fungicidal mixture |
| WO1999011129A1 (en) * | 1997-09-04 | 1999-03-11 | E.I. Du Pont De Nemours And Company | Enantiomerically enriched compositions and their pesticidal use |
| WO1999018102A1 (en) * | 1997-10-08 | 1999-04-15 | E.I. Du Pont De Nemours And Company | Fungicidal and arthropodicidal cyclic amides |
| DE19745650A1 (de) * | 1997-10-16 | 1999-04-22 | Basf Ag | Substituierte Phenylcarbamate, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen |
| EP0934935A1 (de) | 1998-02-05 | 1999-08-11 | Basf Aktiengesellschaft | Heterocyclylsubstituierte Phenylverbindungen, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen |
| DE19813354A1 (de) * | 1998-03-26 | 1999-09-30 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
| TW536387B (en) | 1998-04-23 | 2003-06-11 | Sumitomo Chemical Co | Pyrazolinone compound |
| WO2000007999A1 (fr) | 1998-08-03 | 2000-02-17 | Sumitomo Chemical Company, Limited | Derives de triazolone, leur utilisation, et produits intermediaires obtenus a partir de ces derives |
| WO2001019803A1 (de) * | 1999-09-15 | 2001-03-22 | Basf Aktiengesellschaft | Ungesättigte oximether und ihre verwendung zur bekämpfung von schadpilzen und tierischen schädlingen |
| GB9924692D0 (en) * | 1999-10-20 | 1999-12-22 | Hoechst Schering Agrevo Gmbh | Wood treatment |
| RS20050161A (en) | 2002-08-08 | 2007-09-21 | Amgen Inc., | Vanilloid receptor ligands and their use in treatments |
| EP1745034A1 (en) | 2004-02-11 | 2007-01-24 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| MY139645A (en) | 2004-02-11 | 2009-10-30 | Amgen Inc | Vanilloid receptor ligands and their use in treatments |
| DOP2005000123A (es) | 2004-07-02 | 2011-07-15 | Merck Sharp & Dohme | Inhibidores de cetp |
| US7301022B2 (en) | 2005-02-15 | 2007-11-27 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| EA028392B1 (ru) * | 2007-08-13 | 2017-11-30 | Монсанто Текнолоджи Ллс | Композиции и способы контроля нематод |
| JP5788404B2 (ja) | 2009-12-11 | 2015-09-30 | アウトイフオンイ トヘラペウトイクス リミテッド | イミダゾリジンジオン誘導体 |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| WO2011133920A1 (en) | 2010-04-23 | 2011-10-27 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| PL2649066T3 (pl) | 2010-12-06 | 2017-04-28 | Autifony Therapeutics Limited | Pochodne hydantoiny przydatne jako inhibitory KV3 |
| US8759380B2 (en) | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| US9193704B2 (en) | 2011-06-07 | 2015-11-24 | Autifony Therapeutics Limited | Hydantoin derivatives as KV3 inhibitors |
| AR086744A1 (es) * | 2011-06-28 | 2014-01-22 | Nippon Soda Co | Compuesto heterociclico conteniendo nitrogeno y fungicida para el uso en agricultura y jardineria |
| WO2013058256A1 (ja) * | 2011-10-17 | 2013-04-25 | 日本曹達株式会社 | 含窒素ヘテロ環化合物および農園芸用殺菌剤 |
| JP6075182B2 (ja) * | 2012-04-27 | 2017-02-08 | 住友化学株式会社 | テトラゾリノン化合物及びその用途 |
| US9422252B2 (en) | 2012-05-22 | 2016-08-23 | Autifony Therapeutics Limited | Triazoles as Kv3 inhibitors |
| JP2015517563A (ja) | 2012-05-22 | 2015-06-22 | アウトイフオンイ トヘラペウトイクス リミテッド | Kv3阻害剤としてのヒダントイン誘導体 |
| TW201609710A (zh) * | 2013-12-10 | 2016-03-16 | 杜邦股份有限公司 | 除草用經取代嘧啶氧基苯化合物 |
| DK3683215T3 (da) * | 2017-09-11 | 2023-08-28 | Sumitomo Chemical Co | Tetrazolinonforbindelse og anvendelse deraf |
| JP7050075B2 (ja) * | 2017-09-11 | 2022-04-07 | 住友化学株式会社 | テトラゾリノン化合物およびその用途 |
| WO2020177729A1 (zh) * | 2019-03-06 | 2020-09-10 | 江苏恒瑞医药股份有限公司 | 稠合芳香环类衍生物、其制备方法及其在医药上的应用 |
| GB201916676D0 (en) * | 2019-11-15 | 2020-01-01 | Syngenta Crop Protection Ag | Improvements in or relating to organic compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69211841T2 (de) * | 1991-03-19 | 1997-01-09 | Ciba Geigy Ag | Verbindungen mit herbiziden,acarizider und insektizider wirkung |
| DE4109208A1 (de) * | 1991-03-21 | 1992-09-24 | Bayer Ag | 3-hydroxy-4-aryl-5-oxo-pyrazolin-derivate |
| DE4413669A1 (de) * | 1993-07-05 | 1995-01-12 | Bayer Ag | Substituierte Aryl-ketoenolheterocyclen |
| HU215648B (hu) * | 1993-11-19 | 1999-01-28 | E.I. Du Pont De Nemours And Company | Ciklusos amidszármazékok, hatóanyagként ezeket tartalmazó fungicid készítmények és alkalmazásuk |
| IL115894A0 (en) * | 1994-12-08 | 1996-01-31 | Du Pont | Organosilanes and organogermanes and their use |
| JPH11501015A (ja) * | 1995-02-24 | 1999-01-26 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 殺菌・殺カビ性環式アミド |
-
1996
- 1996-06-13 NZ NZ310884A patent/NZ310884A/en unknown
- 1996-06-13 KR KR1019970709541A patent/KR19990028230A/ko not_active Withdrawn
- 1996-06-13 JP JP9503876A patent/JPH11508257A/ja active Pending
- 1996-06-13 BR BR9609001A patent/BR9609001A/pt unknown
- 1996-06-13 WO PCT/US1996/010326 patent/WO1997000612A1/en not_active Application Discontinuation
- 1996-06-13 MX MX9710259A patent/MX9710259A/es unknown
- 1996-06-13 HU HU9901228A patent/HUP9901228A3/hu unknown
- 1996-06-13 PL PL96324291A patent/PL324291A1/xx unknown
- 1996-06-13 AU AU61770/96A patent/AU6177096A/en not_active Abandoned
- 1996-06-13 CZ CZ973940A patent/CZ394097A3/cs unknown
- 1996-06-13 IL IL12267096A patent/IL122670A0/xx unknown
- 1996-06-13 EP EP96919422A patent/EP0836384A1/en not_active Withdrawn
- 1996-06-19 ZA ZA9605196A patent/ZA965196B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11508257A (ja) | 1999-07-21 |
| IL122670A0 (en) | 1998-08-16 |
| WO1997000612A1 (en) | 1997-01-09 |
| ZA965196B (en) | 1997-12-19 |
| HUP9901228A2 (hu) | 1999-07-28 |
| CZ394097A3 (cs) | 1998-09-16 |
| AU6177096A (en) | 1997-01-22 |
| PL324291A1 (en) | 1998-05-11 |
| BR9609001A (pt) | 1999-06-29 |
| HUP9901228A3 (en) | 2001-11-28 |
| EP0836384A1 (en) | 1998-04-22 |
| NZ310884A (en) | 1999-04-29 |
| MX9710259A (es) | 1998-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 19971219 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |