BR122017015898B1 - Composto, composições fungicidas e método para controlar doenças de planta - Google Patents

Info

Publication number

BR122017015898B1

BR122017015898B1 BR122017015898-8A BR122017015898A BR122017015898B1 BR 122017015898 B1 BR122017015898 B1 BR 122017015898B1 BR 122017015898 A BR122017015898 A BR 122017015898A BR 122017015898 B1 BR122017015898 B1 BR 122017015898B1

Authority

BR

Brazil

Prior art keywords

compound

formula

chloro

fungicides

methyl

Prior art date

2010-09-01

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 677
• 239000000203 mixture Substances 0.000 title claims abstract description 156
• 238000000034 method Methods 0.000 title claims abstract description 57
• 201000010099 disease Diseases 0.000 title claims abstract description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 36
• 150000003839 salts Chemical class 0.000 claims abstract description 33
• 239000000417 fungicide Substances 0.000 claims description 253
• -1 2-chloro-4-fluorophenyl Chemical group 0.000 claims description 233
• 125000001424 substituent group Chemical group 0.000 claims description 133
• 230000000855 fungicidal effect Effects 0.000 claims description 98
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
• 229910052736 halogen Inorganic materials 0.000 claims description 51
• 239000007787 solid Substances 0.000 claims description 41
• 125000005843 halogen group Chemical group 0.000 claims description 38
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• 239000007788 liquid Substances 0.000 claims description 34
• 229910052794 bromium Inorganic materials 0.000 claims description 27
• 229910052801 chlorine Inorganic materials 0.000 claims description 27
• 239000004094 surface-active agent Substances 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 244000000004 fungal plant pathogen Species 0.000 claims description 7
• VAGLJWYKXJYGHQ-UHFFFAOYSA-N 3-chloro-4-[4-(2-chloro-4-fluorophenoxy)-2,5-dimethylpyrazol-3-yl]benzonitrile Chemical compound CC1=NN(C)C(C=2C(=CC(=CC=2)C#N)Cl)=C1OC1=CC=C(F)C=C1Cl VAGLJWYKXJYGHQ-UHFFFAOYSA-N 0.000 claims description 2
• VPTVABWVTXURCW-UHFFFAOYSA-N 3-chloro-4-[5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]oxybenzonitrile Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1OC1=CC=C(C#N)C=C1Cl VPTVABWVTXURCW-UHFFFAOYSA-N 0.000 claims description 2
• YBCRYNSCGIUVLE-UHFFFAOYSA-N 4-(2-chloro-4-fluorobenzoyl)-5-(2,4-difluorophenyl)-1-methylpyrazole-3-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C=1N(C)N=C(C#N)C=1C(=O)C1=CC=C(F)C=C1Cl YBCRYNSCGIUVLE-UHFFFAOYSA-N 0.000 claims description 2
• UTFCFZSOUVJAAZ-UHFFFAOYSA-N 4-[[5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]amino]-3,5-difluorobenzonitrile Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1NC1=C(F)C=C(C#N)C=C1F UTFCFZSOUVJAAZ-UHFFFAOYSA-N 0.000 claims description 2
• HZMFFXSDUMADLO-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenoxy)-5-(2-chloro-4-methoxyphenyl)-1,3-dimethylpyrazole Chemical compound ClC1=CC(OC)=CC=C1C(N(N=C1C)C)=C1OC1=CC=C(F)C=C1Cl HZMFFXSDUMADLO-UHFFFAOYSA-N 0.000 claims 1
• NREHVHRBQIIGAJ-UHFFFAOYSA-N 5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1N NREHVHRBQIIGAJ-UHFFFAOYSA-N 0.000 claims 1
• KAICHMJALBRCMR-UHFFFAOYSA-N 5-(2-chloro-4-methoxyphenyl)-4-(2,4-difluorophenoxy)-1,3-dimethylpyrazole Chemical compound ClC1=CC(OC)=CC=C1C(N(N=C1C)C)=C1OC1=CC=C(F)C=C1F KAICHMJALBRCMR-UHFFFAOYSA-N 0.000 claims 1
• JLUJLAXFYSMHCJ-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4-difluorophenyl)methanone Chemical compound CC1=NN(C)C(C=2C(=CC(Cl)=CC=2)Cl)=C1C(=O)C1=CC=C(F)C=C1F JLUJLAXFYSMHCJ-UHFFFAOYSA-N 0.000 claims 1
• 244000053095 fungal pathogen Species 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
• 230000009471 action Effects 0.000 description 68
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
• 239000011541 reaction mixture Substances 0.000 description 47
• 125000000217 alkyl group Chemical group 0.000 description 46
• 238000002360 preparation method Methods 0.000 description 45
• 241000196324 Embryophyta Species 0.000 description 43
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 230000002829 reductive effect Effects 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
• 125000004970 halomethyl group Chemical group 0.000 description 35
• 239000000126 substance Substances 0.000 description 34
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
• 125000003545 alkoxy group Chemical group 0.000 description 32
• 239000000460 chlorine Substances 0.000 description 31
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 31
• 239000000463 material Substances 0.000 description 31
• 230000015572 biosynthetic process Effects 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• 230000012010 growth Effects 0.000 description 28
• 239000000047 product Substances 0.000 description 28
• 241000233866 Fungi Species 0.000 description 27
• 229910052799 carbon Inorganic materials 0.000 description 27
• 238000012360 testing method Methods 0.000 description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• 125000004432 carbon atom Chemical group C* 0.000 description 26
• 238000009472 formulation Methods 0.000 description 26
• 125000001188 haloalkyl group Chemical group 0.000 description 26
• 239000000243 solution Substances 0.000 description 26
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 25
• HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 25
• 229940125773 compound 10 Drugs 0.000 description 25
• 229940126543 compound 14 Drugs 0.000 description 25
• 229940126214 compound 3 Drugs 0.000 description 25
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 25
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
• PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 24
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 24
• 235000019441 ethanol Nutrition 0.000 description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
• 239000000725 suspension Substances 0.000 description 24
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 23
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 23
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 23
• OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 23
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 23
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 23
• 229940126657 Compound 17 Drugs 0.000 description 23
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 23
• 238000006243 chemical reaction Methods 0.000 description 23
• 229940125797 compound 12 Drugs 0.000 description 23
• 229940125877 compound 31 Drugs 0.000 description 23
• 229940125878 compound 36 Drugs 0.000 description 23
• ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 22
• 229940126639 Compound 33 Drugs 0.000 description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 description 22
• 229920006395 saturated elastomer Polymers 0.000 description 22
• QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 21
• UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 21
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 21
• 229940126086 compound 21 Drugs 0.000 description 21
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 20
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 20
• 238000005160 1H NMR spectroscopy Methods 0.000 description 20
• 239000003480 eluent Substances 0.000 description 20
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 19
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 19
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 19
• 125000004414 alkyl thio group Chemical group 0.000 description 19
• 229940125807 compound 37 Drugs 0.000 description 19
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• 238000005481 NMR spectroscopy Methods 0.000 description 18
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• 125000000623 heterocyclic group Chemical group 0.000 description 18
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• YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 18
• 238000003786 synthesis reaction Methods 0.000 description 18
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• 229930182558 Sterol Natural products 0.000 description 17
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• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 16
• 150000003432 sterols Chemical class 0.000 description 16
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 15
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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• 239000003085 diluting agent Substances 0.000 description 15
• 230000002538 fungal effect Effects 0.000 description 15
• 150000002367 halogens Chemical class 0.000 description 15
• 125000004076 pyridyl group Chemical group 0.000 description 15
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
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• 125000004448 alkyl carbonyl group Chemical group 0.000 description 14
• 125000004966 cyanoalkyl group Chemical group 0.000 description 14
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 14
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
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• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 13
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• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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