HU204971B - Insecticidal, acaricidal and nematocidal compositions comprising arylpyrrole derivatives as active ingredient and process for producing arylpyrrole derivatives - Google Patents

Info

Publication number

HU204971B

HU204971B HU401688A HU401688A HU204971B HU 204971 B HU204971 B HU 204971B HU 401688 A HU401688 A HU 401688A HU 401688 A HU401688 A HU 401688A HU 204971 B HU204971 B HU 204971B

Authority

HU

Hungary

Prior art keywords

pyrrole

carbonitrile

trifluoromethyl

chlorophenyl

dichloro

Prior art date

1987-07-29

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 14
• 239000004480 active ingredient Substances 0.000 title claims description 11
• 230000000749 insecticidal effect Effects 0.000 title claims description 8
• 230000000895 acaricidal effect Effects 0.000 title claims description 7
• 239000000203 mixture Substances 0.000 title description 84
• 230000001069 nematicidal effect Effects 0.000 title description 3
• 239000007787 solid Substances 0.000 claims description 151
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 80
• 239000000460 chlorine Substances 0.000 claims description 64
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• 229910052794 bromium Inorganic materials 0.000 claims description 52
• -1 chloro, bromo, iodo Chemical group 0.000 claims description 51
• 150000001875 compounds Chemical class 0.000 claims description 51
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 44
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 44
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 38
• 229910052801 chlorine Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 125000001246 bromo group Chemical group Br* 0.000 claims description 23
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000002346 iodo group Chemical group I* 0.000 claims description 8
• JTWHVBNYYWFXSI-UHFFFAOYSA-N 2-nitro-1-phenylethanone Chemical class [O-][N+](=O)CC(=O)C1=CC=CC=C1 JTWHVBNYYWFXSI-UHFFFAOYSA-N 0.000 claims description 7
• ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical group N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 claims description 7
• 239000007788 liquid Substances 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 230000002140 halogenating effect Effects 0.000 claims description 5
• 239000005645 nematicide Substances 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 239000003960 organic solvent Substances 0.000 claims description 3
• 239000004094 surface-active agent Substances 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• 239000011707 mineral Substances 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
• 125000001424 substituent group Chemical group 0.000 claims description 2
• 150000002367 halogens Chemical group 0.000 claims 7
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 1
• PIAOLBVUVDXHHL-UHFFFAOYSA-N 2-nitroethenylbenzene Chemical class [O-][N+](=O)C=CC1=CC=CC=C1 PIAOLBVUVDXHHL-UHFFFAOYSA-N 0.000 claims 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
• 239000000969 carrier Substances 0.000 claims 1
• 239000003085 diluting agent Substances 0.000 claims 1
• 150000007522 mineralic acids Chemical class 0.000 claims 1
• 150000007524 organic acids Chemical class 0.000 claims 1
• KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 167
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 118
• 239000000243 solution Substances 0.000 description 111
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 98
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
• 239000011541 reaction mixture Substances 0.000 description 62
• 235000019439 ethyl acetate Nutrition 0.000 description 56
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 53
• 229910052757 nitrogen Inorganic materials 0.000 description 50
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 44
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 238000003756 stirring Methods 0.000 description 35
• 238000012360 testing method Methods 0.000 description 35
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 34
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
• 239000000741 silica gel Substances 0.000 description 30
• 229910002027 silica gel Inorganic materials 0.000 description 30
• 239000002244 precipitate Substances 0.000 description 28
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 24
• PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 235000019341 magnesium sulphate Nutrition 0.000 description 23
• 238000002844 melting Methods 0.000 description 22
• 230000008018 melting Effects 0.000 description 22
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000000047 product Substances 0.000 description 21
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 19
• 239000000725 suspension Substances 0.000 description 19
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 18
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 18
• 229960000583 acetic acid Drugs 0.000 description 18
• 238000000921 elemental analysis Methods 0.000 description 18
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
• 239000003921 oil Substances 0.000 description 17
• 235000019198 oils Nutrition 0.000 description 17
• 230000000694 effects Effects 0.000 description 15
• 239000012044 organic layer Substances 0.000 description 15
• 241000196324 Embryophyta Species 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• 241001465754 Metazoa Species 0.000 description 14
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 14
• 239000000706 filtrate Substances 0.000 description 13
• 238000010992 reflux Methods 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
• 238000004458 analytical method Methods 0.000 description 11
• 238000001816 cooling Methods 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 150000002825 nitriles Chemical class 0.000 description 11
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 11
• 125000003118 aryl group Chemical group 0.000 description 10
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 10
• FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 10
• 239000012071 phase Substances 0.000 description 10
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 10
• ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 9
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• 239000002689 soil Substances 0.000 description 9
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
• 238000005160 1H NMR spectroscopy Methods 0.000 description 8
• SRTONGWZJVFIHQ-UHFFFAOYSA-N 2-phenyl-1h-pyrrole-3-carbonitrile Chemical class C1=CNC(C=2C=CC=CC=2)=C1C#N SRTONGWZJVFIHQ-UHFFFAOYSA-N 0.000 description 8
• 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 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 229910052938 sodium sulfate Inorganic materials 0.000 description 8
• 235000011152 sodium sulphate Nutrition 0.000 description 8
• 238000004809 thin layer chromatography Methods 0.000 description 8
• BCVRADPAEJGQFB-UHFFFAOYSA-N 3-nitro-2-phenyl-1h-pyrrole Chemical class C1=CNC(C=2C=CC=CC=2)=C1[N+](=O)[O-] BCVRADPAEJGQFB-UHFFFAOYSA-N 0.000 description 7
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 7
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
• 238000005481 NMR spectroscopy Methods 0.000 description 7
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
• 241001521235 Spodoptera eridania Species 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 230000009885 systemic effect Effects 0.000 description 7
• 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 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 241000238631 Hexapoda Species 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• 239000005708 Sodium hypochlorite Substances 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 239000003814 drug Substances 0.000 description 6
• 239000000839 emulsion Substances 0.000 description 6
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 6
• 238000001953 recrystallisation Methods 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
• 241000238876 Acari Species 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
• 241000244206 Nematoda Species 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 239000012267 brine Substances 0.000 description 5
• 150000001721 carbon Chemical group 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 239000012362 glacial acetic acid Substances 0.000 description 5
• 125000005843 halogen group Chemical group 0.000 description 5
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• 239000012299 nitrogen atmosphere Substances 0.000 description 5
• 239000000123 paper Substances 0.000 description 5
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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 4
• SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
• HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 4
• ROKJAOFULHUNSQ-UHFFFAOYSA-N 2,3-dichloro-4-nitro-5-phenyl-1h-pyrrole Chemical compound ClC1=C(Cl)NC(C=2C=CC=CC=2)=C1[N+](=O)[O-] ROKJAOFULHUNSQ-UHFFFAOYSA-N 0.000 description 4
• IOOIRDCQSWZIRT-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-1h-pyrrole-3-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=C(C#N)C=CN1 IOOIRDCQSWZIRT-UHFFFAOYSA-N 0.000 description 4
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
• 241000288178 Autoba abrupta Species 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• 241000256244 Heliothis virescens Species 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
• 238000003556 assay Methods 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 239000000284 extract Substances 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 238000003818 flash chromatography Methods 0.000 description 4
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 238000011835 investigation Methods 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 235000016709 nutrition Nutrition 0.000 description 4
• 239000002002 slurry Substances 0.000 description 4
• 239000000126 substance Substances 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
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
• RYQGPAMUUQAEEM-UHFFFAOYSA-N 1h-pyrrole-2,4-dicarbonitrile Chemical compound N#CC1=CNC(C#N)=C1 RYQGPAMUUQAEEM-UHFFFAOYSA-N 0.000 description 3
• LEXPMHCGHUCQSN-UHFFFAOYSA-N 2,3-dibromo-4-nitro-5-phenyl-1h-pyrrole Chemical compound BrC1=C(Br)NC(C=2C=CC=CC=2)=C1[N+](=O)[O-] LEXPMHCGHUCQSN-UHFFFAOYSA-N 0.000 description 3
• OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 3
• AZTYHYHSDPMHRA-UHFFFAOYSA-N 2-formamido-2-phenylacetic acid Chemical compound O=CNC(C(=O)O)C1=CC=CC=C1 AZTYHYHSDPMHRA-UHFFFAOYSA-N 0.000 description 3
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