CA1332060C - Arylpyrrole insecticidal acaricidal and nematicidal agents and method for the preparation thereof - Google Patents
Arylpyrrole insecticidal acaricidal and nematicidal agents and method for the preparation thereofInfo
- Publication number
- CA1332060C CA1332060C CA 573124 CA573124A CA1332060C CA 1332060 C CA1332060 C CA 1332060C CA 573124 CA573124 CA 573124 CA 573124 A CA573124 A CA 573124A CA 1332060 C CA1332060 C CA 1332060C
- Authority
- CA
- Canada
- Prior art keywords
- pyrrole
- alkyl
- alkoxy
- alpha
- carbonitrile
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 42
- 230000000895 acaricidal effect Effects 0.000 title abstract description 9
- 230000000749 insecticidal effect Effects 0.000 title abstract description 9
- 239000005645 nematicide Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 241000238631 Hexapoda Species 0.000 claims abstract description 18
- 241000244206 Nematoda Species 0.000 claims abstract description 17
- 239000002689 soil Substances 0.000 claims abstract description 13
- 230000002633 protecting effect Effects 0.000 claims abstract description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 98
- 239000000203 mixture Substances 0.000 claims description 91
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- 229910001868 water Inorganic materials 0.000 claims description 72
- 229910052794 bromium Inorganic materials 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- 229910052731 fluorine Inorganic materials 0.000 claims description 51
- PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 33
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- -1 R4 is H Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims description 21
- 229910052740 iodine Inorganic materials 0.000 claims description 20
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 20
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 241000238876 Acari Species 0.000 claims description 16
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 11
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 claims description 10
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 10
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 10
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical compound N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 claims description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 claims description 6
- JTWHVBNYYWFXSI-UHFFFAOYSA-N 2-nitro-1-phenylethanone Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1 JTWHVBNYYWFXSI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- GWDQLAOKLMLQSJ-UHFFFAOYSA-N 4,5-dichloro-2-(3,4-dichlorophenyl)-1h-pyrrole-3-carbonitrile Chemical compound ClC1=C(Cl)NC(C=2C=C(Cl)C(Cl)=CC=2)=C1C#N GWDQLAOKLMLQSJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- OWFIVIKUVQYGSV-UHFFFAOYSA-N 2,3-dichloro-5-(3,4-dichlorophenyl)-4-nitro-1h-pyrrole Chemical compound ClC1=C(Cl)NC(C=2C=C(Cl)C(Cl)=CC=2)=C1[N+](=O)[O-] OWFIVIKUVQYGSV-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 238000009395 breeding Methods 0.000 claims description 2
- 230000001488 breeding effect Effects 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- QLIJLXJQOZCMJD-UHFFFAOYSA-N 2,4-dibromo-5-(4-chlorophenyl)-1h-pyrrole-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1=C(Br)C(C#N)=C(Br)N1 QLIJLXJQOZCMJD-UHFFFAOYSA-N 0.000 claims 1
- QPGRRLAHBIMLIS-UHFFFAOYSA-N 3,4-dibromo-5-(3,4-dichlorophenyl)-1h-pyrrole-2-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=C(Br)C(Br)=C(C#N)N1 QPGRRLAHBIMLIS-UHFFFAOYSA-N 0.000 claims 1
- WZUSKVBYPYISLI-UHFFFAOYSA-N 3-[4-(trifluoromethoxy)phenyl]prop-2-enenitrile Chemical compound FC(F)(F)OC1=CC=C(C=CC#N)C=C1 WZUSKVBYPYISLI-UHFFFAOYSA-N 0.000 claims 1
- FKDDGCAEIOTEOK-UHFFFAOYSA-N 3-bromo-5-(3,4-dichlorophenyl)-1h-pyrrole-2,4-dicarbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=C(C#N)C(Br)=C(C#N)N1 FKDDGCAEIOTEOK-UHFFFAOYSA-N 0.000 claims 1
- FZSPJLQLJBQRLP-UHFFFAOYSA-N 3-bromo-5-(4-chlorophenyl)-1h-pyrrole-2,4-dicarbonitrile Chemical compound C1=CC(Cl)=CC=C1C1=C(C#N)C(Br)=C(C#N)N1 FZSPJLQLJBQRLP-UHFFFAOYSA-N 0.000 claims 1
- MKOQJYIFQIHDQK-UHFFFAOYSA-N 4-bromo-2-(3,4-dichlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical compound BrC1=C(C(F)(F)F)NC(C=2C=C(Cl)C(Cl)=CC=2)=C1C#N MKOQJYIFQIHDQK-UHFFFAOYSA-N 0.000 claims 1
- DHWIGRQOEXDARJ-PXNMLYILSA-N C(C)OC(C1=C(C=C(C=C1)/C(=C/C#N)/NCC=O)C)(O)OCC Chemical compound C(C)OC(C1=C(C=C(C=C1)/C(=C/C#N)/NCC=O)C)(O)OCC DHWIGRQOEXDARJ-PXNMLYILSA-N 0.000 claims 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- XNFIRYXKTXAHAC-UHFFFAOYSA-N tralopyril Chemical compound BrC1=C(C(F)(F)F)NC(C=2C=CC(Cl)=CC=2)=C1C#N XNFIRYXKTXAHAC-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 230000001069 nematicidal effect Effects 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 description 249
- 239000007787 solid Substances 0.000 description 136
- 239000000243 solution Substances 0.000 description 94
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
- 125000001309 chloro group Chemical group Cl* 0.000 description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- 229940030966 pyrrole Drugs 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
- BQMPGKPTOHKYHS-UHFFFAOYSA-N 1h-pyrrole-2-carbonitrile Chemical compound N#CC1=CC=CN1 BQMPGKPTOHKYHS-UHFFFAOYSA-N 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 238000012360 testing method Methods 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 39
- 229910052799 carbon Inorganic materials 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 238000003756 stirring Methods 0.000 description 36
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 235000019439 ethyl acetate Nutrition 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 25
- 229940093499 ethyl acetate Drugs 0.000 description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 21
- 229960001701 chloroform Drugs 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 150000002825 nitriles Chemical class 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 10
- 125000001246 bromo group Chemical group Br* 0.000 description 10
- 125000000068 chlorophenyl group Chemical group 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
- SRTONGWZJVFIHQ-UHFFFAOYSA-N 2-phenyl-1h-pyrrole-3-carbonitrile Chemical compound C1=CNC(C=2C=CC=CC=2)=C1C#N SRTONGWZJVFIHQ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- RYQGPAMUUQAEEM-UHFFFAOYSA-N 1h-pyrrole-2,4-dicarbonitrile Chemical compound N#CC1=CNC(C#N)=C1 RYQGPAMUUQAEEM-UHFFFAOYSA-N 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- SCOVCVNURFOLTQ-RJRFIUFISA-N (z)-2-bromobut-2-enedinitrile Chemical compound N#CC(/Br)=C/C#N SCOVCVNURFOLTQ-RJRFIUFISA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 241001521235 Spodoptera eridania Species 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- SUHPVIWAYJQMBD-UHFFFAOYSA-N [C].N1C=CC=C1 Chemical compound [C].N1C=CC=C1 SUHPVIWAYJQMBD-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
- 230000004899 motility Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000012258 stirred mixture Substances 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- JNDNHVBXLNJBJB-UHFFFAOYSA-N 2-phenyl-1h-pyrrole-3,4-dicarbonitrile Chemical compound N#CC1=CNC(C=2C=CC=CC=2)=C1C#N JNDNHVBXLNJBJB-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000005708 Sodium hypochlorite Substances 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 238000004452 microanalysis Methods 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000001376 precipitating effect Effects 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 5
- 229960005076 sodium hypochlorite Drugs 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 4
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 4
- MCUUCXWPDYKXRS-UHFFFAOYSA-N 2-bromo-5-phenyl-1h-pyrrole-3,4-dicarbonitrile Chemical compound N#CC1=C(Br)NC(C=2C=CC=CC=2)=C1C#N MCUUCXWPDYKXRS-UHFFFAOYSA-N 0.000 description 4
- BCVRADPAEJGQFB-UHFFFAOYSA-N 3-nitro-2-phenyl-1h-pyrrole Chemical compound C1=CNC(C=2C=CC=CC=2)=C1[N+](=O)[O-] BCVRADPAEJGQFB-UHFFFAOYSA-N 0.000 description 4
- 244000045232 Canavalia ensiformis Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 4
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
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- 101100296027 Streptomyces rimosus oxyL gene Proteins 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000208241 Tropaeolum Species 0.000 description 1
- 240000001260 Tropaeolum majus Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- WQOWSAAWOLTKIL-UHFFFAOYSA-N chloroform ethyl acetate hexane Chemical compound C(C)(=O)OCC.C(Cl)(Cl)Cl.CCCCCC.C(Cl)(Cl)Cl WQOWSAAWOLTKIL-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- RQSAOSHNBJFBJS-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=CNC=C1C1=CC=C(Cl)C=C1 RQSAOSHNBJFBJS-UHFFFAOYSA-N 0.000 description 1
- CXFFDOOXLATWGW-UHFFFAOYSA-N ethyl 5-bromo-4-(4-chlorophenyl)-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=CNC(Br)=C1C1=CC=C(Cl)C=C1 CXFFDOOXLATWGW-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- UTUYRHZFTRKAIR-UHFFFAOYSA-N methyl 2-[3-(3-bromophenyl)-2-chloro-4,5-dicyanopyrrol-1-yl]acetate Chemical compound N#CC1=C(C#N)N(CC(=O)OC)C(Cl)=C1C1=CC=CC(Br)=C1 UTUYRHZFTRKAIR-UHFFFAOYSA-N 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229940049018 mycostatin Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BFNYNEMRWHFIMR-UHFFFAOYSA-N tert-butyl 2-cyanoacetate Chemical compound CC(C)(C)OC(=O)CC#N BFNYNEMRWHFIMR-UHFFFAOYSA-N 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7954587A | 1987-07-29 | 1987-07-29 | |
| US07/079,543 | 1987-07-29 | ||
| US07/079,545 | 1987-07-29 | ||
| US07/079,543 US4857651A (en) | 1987-07-29 | 1987-07-29 | α-(2,3-Di(C1 -C4 alkoxy)ethylamino)-β-cyanostyrene and β-nitrostyrene compounds useful as intermediates in the preparation of insecticidal, acaricidal and nematicidal arylpyrroles and method for the preparation thereof |
| US07/208,841 | 1988-06-23 | ||
| US07/208,841 US5010098A (en) | 1987-07-29 | 1988-06-23 | Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1332060C true CA1332060C (en) | 1994-09-20 |
Family
ID=27373499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 573124 Expired - Lifetime CA1332060C (en) | 1987-07-29 | 1988-07-27 | Arylpyrrole insecticidal acaricidal and nematicidal agents and method for the preparation thereof |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JP2553156B2 (cs) |
| AU (1) | AU610915B2 (cs) |
| CA (1) | CA1332060C (cs) |
| CZ (1) | CZ280795B6 (cs) |
| DK (1) | DK173853B1 (cs) |
| EG (1) | EG19185A (cs) |
| FI (1) | FI91523C (cs) |
| HU (1) | HU204971B (cs) |
| IE (1) | IE62489B1 (cs) |
| IL (1) | IL87222A (cs) |
| NZ (1) | NZ225582A (cs) |
| SK (1) | SK279269B6 (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2087099T3 (es) * | 1989-08-11 | 1996-07-16 | American Cyanamid Co | Agentes arilpirrolicos insecticidas, acaricidas y nematicidas y procedimientos. |
| IL98235A (en) * | 1990-07-31 | 1999-07-14 | American Cyanamid Co | Process for the preparation of insecticidal acaridical and nematicidal 2-aryl-5-(trifluoromethyl) pyrrole compounds and intermediates thereof |
| US5157047A (en) * | 1990-10-18 | 1992-10-20 | American Cyanamid Company | Bis- and tris(trifluoromethyl)arylpyrrole insecticidal and acaricidal agents |
| US5151536A (en) * | 1990-12-17 | 1992-09-29 | American Cyanamid Company | Process for the manufacture of pesticidal 1-(alkoxymethyl) pyrrole compounds |
| US5130328A (en) * | 1991-09-06 | 1992-07-14 | American Cyanamid Company | N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole insecticidal and acaricidal agents |
| US5496845A (en) * | 1994-05-25 | 1996-03-05 | American Cyanamid Co. | Suspension concentrate compositions of arylpyrrole insecticidal and acaricidal agents |
| KR100275222B1 (ko) * | 1995-06-07 | 2001-02-01 | 이노세 히로시 | 피롤 유도체 및 의약 조성물 |
| WO2011161040A1 (en) * | 2010-06-21 | 2011-12-29 | Basf Se | Pesticidal composition comprising a benzoylurea compound and chlorfenapyr and their uses. |
| WO2019131695A1 (ja) * | 2017-12-27 | 2019-07-04 | 日本ケミファ株式会社 | １－［５－（２－フルオロフェニル）－１－（ピリジン－３－イルスルホニル）－１ｈ－ピロ－ル－３－イル］－ｎ－メチルメタンアミンモノフマル酸塩の製造法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3065675D1 (en) * | 1979-06-28 | 1983-12-29 | Ciba Geigy Ag | Stabilizers for thermoplasts that contain chlorine |
-
1988
- 1988-07-26 IL IL87222A patent/IL87222A/xx not_active IP Right Cessation
- 1988-07-27 NZ NZ22558288A patent/NZ225582A/en unknown
- 1988-07-27 CA CA 573124 patent/CA1332060C/en not_active Expired - Lifetime
- 1988-07-28 AU AU20117/88A patent/AU610915B2/en not_active Expired
- 1988-07-28 FI FI883554A patent/FI91523C/fi active IP Right Grant
- 1988-07-28 CZ CS885360A patent/CZ280795B6/cs not_active IP Right Cessation
- 1988-07-28 IE IE231588A patent/IE62489B1/en not_active IP Right Cessation
- 1988-07-28 SK SK5360-88A patent/SK279269B6/sk unknown
- 1988-07-28 DK DK422488A patent/DK173853B1/da not_active IP Right Cessation
- 1988-07-28 HU HU401688A patent/HU204971B/hu unknown
- 1988-07-29 JP JP63190485A patent/JP2553156B2/ja not_active Expired - Lifetime
- 1988-07-31 EG EG40988A patent/EG19185A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| AU2011788A (en) | 1989-02-09 |
| DK422488A (da) | 1989-01-30 |
| SK536088A3 (en) | 1998-08-05 |
| AU610915B2 (en) | 1991-05-30 |
| CZ280795B6 (cs) | 1996-04-17 |
| CZ536088A3 (en) | 1996-01-17 |
| DK422488D0 (da) | 1988-07-28 |
| FI91523B (fi) | 1994-03-31 |
| IL87222A0 (en) | 1988-12-30 |
| JPH01104042A (ja) | 1989-04-21 |
| NZ225582A (en) | 1992-01-29 |
| HUT48797A (en) | 1989-07-28 |
| FI91523C (fi) | 1994-07-11 |
| FI883554A0 (fi) | 1988-07-28 |
| HU204971B (en) | 1992-03-30 |
| IE882315L (en) | 1989-01-29 |
| IE62489B1 (en) | 1995-02-08 |
| SK279269B6 (sk) | 1998-08-05 |
| IL87222A (en) | 1993-04-04 |
| JP2553156B2 (ja) | 1996-11-13 |
| EG19185A (en) | 1994-09-29 |
| DK173853B1 (da) | 2001-12-27 |
| FI883554A7 (fi) | 1989-01-30 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |