DK173853B1 - 2,3,4,5-Tetrasubstituerede pyrroler, fremgangsmåde til deres fremstilling, alfa,beta-disubstituerede styrener til brug ved udøvelse af fremgangsmåden samt pyrrolernes anvendelse som insecticider, acaricider og nematodicider - Google Patents
2,3,4,5-Tetrasubstituerede pyrroler, fremgangsmåde til deres fremstilling, alfa,beta-disubstituerede styrener til brug ved udøvelse af fremgangsmåden samt pyrrolernes anvendelse som insecticider, acaricider og nematodicider Download PDFInfo
- Publication number
- DK173853B1 DK173853B1 DK422488A DK422488A DK173853B1 DK 173853 B1 DK173853 B1 DK 173853B1 DK 422488 A DK422488 A DK 422488A DK 422488 A DK422488 A DK 422488A DK 173853 B1 DK173853 B1 DK 173853B1
- Authority
- DK
- Denmark
- Prior art keywords
- pyrrole
- carbonitrile
- dichloro
- dichlorophenyl
- chlorophenyl
- Prior art date
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- -1 2,3,4,5-Tetra-substituted pyrroles Chemical class 0.000 title claims description 73
- 238000002360 preparation method Methods 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 38
- 230000000895 acaricidal effect Effects 0.000 title claims description 10
- 239000002917 insecticide Substances 0.000 title claims description 7
- 239000000642 acaricide Substances 0.000 title claims description 6
- 150000003233 pyrroles Chemical class 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 51
- 229910052794 bromium Inorganic materials 0.000 claims description 49
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 18
- PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 241000238876 Acari Species 0.000 claims description 16
- 241000238631 Hexapoda Species 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 15
- 241000244206 Nematoda Species 0.000 claims description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 239000002689 soil Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 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 8
- GWDQLAOKLMLQSJ-UHFFFAOYSA-N 4,5-dichloro-2-(3,4-dichlorophenyl)-1h-pyrrole-3-carbonitrile Chemical group ClC1=C(Cl)NC(C=2C=C(Cl)C(Cl)=CC=2)=C1C#N GWDQLAOKLMLQSJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical compound N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 230000001069 nematicidal effect Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 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 description 4
- 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 description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 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 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 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 description 4
- 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 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- FWKJYENLIDAWOS-SDQBBNPISA-N (z)-3-(4-methylphenyl)-3-(2-oxoethylamino)prop-2-enenitrile Chemical compound CC1=CC=C(C(\NCC=O)=C\C#N)C=C1 FWKJYENLIDAWOS-SDQBBNPISA-N 0.000 claims description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 201000002266 mite infestation Diseases 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 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 3
- JJESCIWXHPTJKY-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-(trifluoromethyl)-1h-pyrrole-2,4-dicarbonitrile Chemical compound FC(F)(F)C1=C(C#N)NC(C=2C=CC(Cl)=CC=2)=C1C#N JJESCIWXHPTJKY-UHFFFAOYSA-N 0.000 claims 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 3
- AEEUNGBWCIBCJF-VZUCSPMQSA-N (E)-3-(4-chlorophenyl)-3-(2-oxoethylamino)prop-2-enenitrile Chemical group ClC1=CC=C(C(\NCC=O)=C/C#N)C=C1 AEEUNGBWCIBCJF-VZUCSPMQSA-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
- 238000009395 breeding Methods 0.000 claims 1
- 230000001488 breeding effect Effects 0.000 claims 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims 1
- 150000003440 styrenes Chemical class 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 207
- 239000007787 solid Substances 0.000 description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- 239000000243 solution Substances 0.000 description 90
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 69
- 125000001309 chloro group Chemical group Cl* 0.000 description 63
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 33
- 238000012360 testing method Methods 0.000 description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000011282 treatment Methods 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
- 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 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 238000000746 purification Methods 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
- 230000000694 effects Effects 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241001521235 Spodoptera eridania Species 0.000 description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 230000004899 motility Effects 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000012258 stirred mixture Substances 0.000 description 6
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 5
- SCOVCVNURFOLTQ-RJRFIUFISA-N (z)-2-bromobut-2-enedinitrile Chemical compound N#CC(/Br)=C/C#N SCOVCVNURFOLTQ-RJRFIUFISA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- AYHPEZVIRQXWOM-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-pyrrole-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1=C(C#N)C=CN1 AYHPEZVIRQXWOM-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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 5
- 244000045232 Canavalia ensiformis Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- SUHPVIWAYJQMBD-UHFFFAOYSA-N [C].N1C=CC=C1 Chemical compound [C].N1C=CC=C1 SUHPVIWAYJQMBD-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
- 238000004452 microanalysis Methods 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- BQMPGKPTOHKYHS-UHFFFAOYSA-N 1h-pyrrole-2-carbonitrile Chemical compound N#CC1=CC=CN1 BQMPGKPTOHKYHS-UHFFFAOYSA-N 0.000 description 4
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-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
- 241001674044 Blattodea Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000010438 heat treatment Methods 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
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- 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
- 108010072897 transcription factor Brn-2 Proteins 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- PIAOLBVUVDXHHL-VOTSOKGWSA-N β-nitrostyrene Chemical compound [O-][N+](=O)\C=C\C1=CC=CC=C1 PIAOLBVUVDXHHL-VOTSOKGWSA-N 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 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 |
| US7954587 | 1987-07-29 | ||
| US7954387 | 1987-07-29 | ||
| US07/208,841 US5010098A (en) | 1987-07-29 | 1988-06-23 | Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof |
| US20884188 | 1988-06-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK422488D0 DK422488D0 (da) | 1988-07-28 |
| DK422488A DK422488A (da) | 1989-01-30 |
| DK173853B1 true DK173853B1 (da) | 2001-12-27 |
Family
ID=27373499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK422488A DK173853B1 (da) | 1987-07-29 | 1988-07-28 | 2,3,4,5-Tetrasubstituerede pyrroler, fremgangsmåde til deres fremstilling, alfa,beta-disubstituerede styrener til brug ved udøvelse af fremgangsmåden samt pyrrolernes anvendelse som insecticider, acaricider og nematodicider |
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 |
|---|---|---|---|---|
| ATE137745T1 (de) * | 1989-08-11 | 1996-05-15 | American Cyanamid Co | Arylpyrrol enthaltende insekticidale, acaricidale und nematicidale mittel sowie verfahren zu ihrer herstellung |
| 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 |
| RU2166941C2 (ru) * | 1995-06-07 | 2001-05-20 | Ниппон Синяку Ко., Лтд. | Производные пиррола и фармацевтическая композиция на их основе |
| KR101847665B1 (ko) * | 2010-06-21 | 2018-04-10 | 바스프 에스이 | 벤조일우레아 화합물 및 클로르페나피르를 포함하는 살충 조성물 및 그의 용도 |
| JP7227925B2 (ja) * | 2017-12-27 | 2023-02-22 | 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 |
|---|---|---|---|---|
| EP0022087B1 (de) * | 1979-06-28 | 1983-11-23 | Ciba-Geigy Ag | Stabilisatoren für chlorhaltige Thermoplaste |
-
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 IE IE231588A patent/IE62489B1/en not_active IP Right Cessation
- 1988-07-28 DK DK422488A patent/DK173853B1/da not_active IP Right Cessation
- 1988-07-28 CZ CS885360A patent/CZ280795B6/cs not_active IP Right Cessation
- 1988-07-28 SK SK5360-88A patent/SK279269B6/sk unknown
- 1988-07-28 HU HU401688A patent/HU204971B/hu unknown
- 1988-07-28 FI FI883554A patent/FI91523C/fi active IP Right Grant
- 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 |
|---|---|
| AU610915B2 (en) | 1991-05-30 |
| CZ280795B6 (cs) | 1996-04-17 |
| HU204971B (en) | 1992-03-30 |
| DK422488A (da) | 1989-01-30 |
| DK422488D0 (da) | 1988-07-28 |
| SK536088A3 (en) | 1998-08-05 |
| IL87222A0 (en) | 1988-12-30 |
| FI883554A0 (fi) | 1988-07-28 |
| FI91523B (fi) | 1994-03-31 |
| IL87222A (en) | 1993-04-04 |
| HUT48797A (en) | 1989-07-28 |
| FI883554A7 (fi) | 1989-01-30 |
| AU2011788A (en) | 1989-02-09 |
| IE882315L (en) | 1989-01-29 |
| NZ225582A (en) | 1992-01-29 |
| CA1332060C (en) | 1994-09-20 |
| SK279269B6 (sk) | 1998-08-05 |
| FI91523C (fi) | 1994-07-11 |
| EG19185A (en) | 1994-09-29 |
| CZ536088A3 (en) | 1996-01-17 |
| JPH01104042A (ja) | 1989-04-21 |
| JP2553156B2 (ja) | 1996-11-13 |
| IE62489B1 (en) | 1995-02-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |