BR112017011667B1 - Compostos bicíclicos como agentes de controle de pragas - Google Patents

Info

Publication number

BR112017011667B1

BR112017011667B1 BR112017011667-7A BR112017011667A BR112017011667B1 BR 112017011667 B1 BR112017011667 B1 BR 112017011667B1 BR 112017011667 A BR112017011667 A BR 112017011667A BR 112017011667 B1 BR112017011667 B1 BR 112017011667B1

Authority

BR

Brazil

Prior art keywords

alkyl

radical

group

spp

alkoxy

Prior art date

2014-12-02

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 177
• 239000000203 mixture Substances 0.000 claims abstract description 47
• 238000000034 method Methods 0.000 claims abstract description 42
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 29
• 241000607479 Yersinia pestis Species 0.000 claims abstract description 15
• 241001465754 Metazoa Species 0.000 claims abstract description 12
• -1 C1 -C6-alkoxy Chemical group 0.000 claims description 327
• 229910052739 hydrogen Inorganic materials 0.000 claims description 192
• 239000001257 hydrogen Substances 0.000 claims description 189
• 229910052736 halogen Inorganic materials 0.000 claims description 179
• 229910052760 oxygen Inorganic materials 0.000 claims description 133
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 130
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 128
• 239000001301 oxygen Substances 0.000 claims description 128
• 150000002431 hydrogen Chemical class 0.000 claims description 127
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 101
• 229910052757 nitrogen Inorganic materials 0.000 claims description 96
• 229910052717 sulfur Inorganic materials 0.000 claims description 95
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 62
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 60
• 150000002367 halogens Chemical group 0.000 claims description 55
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
• 229910052731 fluorine Inorganic materials 0.000 claims description 40
• 239000011737 fluorine Substances 0.000 claims description 40
• 125000001188 haloalkyl group Chemical group 0.000 claims description 40
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 239000000460 chlorine Chemical group 0.000 claims description 34
• 229910052801 chlorine Inorganic materials 0.000 claims description 34
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
• 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 32
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
• 229910052794 bromium Inorganic materials 0.000 claims description 30
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 28
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
• VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 16
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 239000004606 Fillers/Extenders Substances 0.000 claims description 7
• 240000000543 Pentas lanceolata Species 0.000 claims description 6
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 239000004094 surface-active agent Substances 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
• 150000001721 carbon Chemical group 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 22
• 230000008569 process Effects 0.000 abstract description 11
• 239000000543 intermediate Substances 0.000 abstract description 6
• 150000003254 radicals Chemical class 0.000 description 398
• 125000005843 halogen group Chemical group 0.000 description 126
• 125000000217 alkyl group Chemical group 0.000 description 118
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 105
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 76
• 239000011593 sulfur Chemical group 0.000 description 76
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 70
• 125000005842 heteroatom Chemical group 0.000 description 63
• 238000006243 chemical reaction Methods 0.000 description 52
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 49
• 125000003545 alkoxy group Chemical group 0.000 description 48
• 125000001072 heteroaryl group Chemical group 0.000 description 46
• 125000004430 oxygen atom Chemical group O* 0.000 description 42
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 40
• 125000000304 alkynyl group Chemical group 0.000 description 38
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 37
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 36
• 125000003342 alkenyl group Chemical group 0.000 description 35
• 125000003118 aryl group Chemical group 0.000 description 35
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 33
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 32
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 31
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 31
• 125000000753 cycloalkyl group Chemical group 0.000 description 31
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 30
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 29
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 27
• 229920006395 saturated elastomer Polymers 0.000 description 27
• 125000000623 heterocyclic group Chemical group 0.000 description 26
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 24
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 23
• 125000006350 alkyl thio alkyl group Chemical group 0.000 description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 22
• 125000004432 carbon atom Chemical group C* 0.000 description 22
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 21
• 239000000575 pesticide Substances 0.000 description 21
• 150000003839 salts Chemical class 0.000 description 21
• 125000004434 sulfur atom Chemical group 0.000 description 21
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 20
• 238000009472 formulation Methods 0.000 description 20
• 239000003112 inhibitor Substances 0.000 description 20
• 125000003226 pyrazolyl group Chemical group 0.000 description 20
• 239000002904 solvent Substances 0.000 description 20
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 19
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 19
• 125000003710 aryl alkyl group Chemical group 0.000 description 19
• 125000002971 oxazolyl group Chemical group 0.000 description 19
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• 125000002541 furyl group Chemical group 0.000 description 18
• 125000004438 haloalkoxy group Chemical group 0.000 description 18
• 125000001544 thienyl group Chemical group 0.000 description 18
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 17
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 17
• 125000000392 cycloalkenyl group Chemical group 0.000 description 17
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 125000000714 pyrimidinyl group Chemical group 0.000 description 15
• 125000000335 thiazolyl group Chemical group 0.000 description 15
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 14
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 14
• 125000003277 amino group Chemical group 0.000 description 14
• 125000004966 cyanoalkyl group Chemical group 0.000 description 14
• 125000004076 pyridyl group Chemical group 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 13
• 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 13
• 125000003373 pyrazinyl group Chemical group 0.000 description 13
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 125000004414 alkyl thio group Chemical group 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 12
• 239000003085 diluting agent Substances 0.000 description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 241000196324 Embryophyta Species 0.000 description 11
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 229910001413 alkali metal ion Inorganic materials 0.000 description 11
• 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 11
• 150000001768 cations Chemical class 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• 125000003831 tetrazolyl group Chemical group 0.000 description 11
• 125000001113 thiadiazolyl group Chemical group 0.000 description 11
• 125000004306 triazinyl group Chemical group 0.000 description 11
• 125000001425 triazolyl group Chemical group 0.000 description 11
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 10
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
• 229910052791 calcium Inorganic materials 0.000 description 10
• 239000011575 calcium Substances 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 125000002757 morpholinyl group Chemical group 0.000 description 10
• 125000001715 oxadiazolyl group Chemical group 0.000 description 10
• 125000003884 phenylalkyl group Chemical group 0.000 description 10
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
• 150000001340 alkali metals Chemical class 0.000 description 9
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 9
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 9
• 125000002883 imidazolyl group Chemical group 0.000 description 9
• 229910052700 potassium Inorganic materials 0.000 description 9
• 239000011591 potassium Substances 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 125000003107 substituted aryl group Chemical group 0.000 description 9
• BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical group ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• YKOWBJJOJNGCAD-SHYZEUOFSA-N [(2r,3s,5r)-3-hydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate Chemical group O=C1N=C(NO)C=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1 YKOWBJJOJNGCAD-SHYZEUOFSA-N 0.000 description 8
• 125000003302 alkenyloxy group Chemical group 0.000 description 8
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
• 125000005133 alkynyloxy group Chemical group 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 239000000969 carrier Substances 0.000 description 8
• 125000000000 cycloalkoxy group Chemical group 0.000 description 8
• ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 8
• 235000019441 ethanol Nutrition 0.000 description 8
• 125000000547 substituted alkyl group Chemical group 0.000 description 8
• 241000894006 Bacteria Species 0.000 description 7
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 7
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
• 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 description 7
• 150000002170 ethers Chemical class 0.000 description 7
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 7
• 229910052744 lithium Inorganic materials 0.000 description 7
• 229910052749 magnesium Inorganic materials 0.000 description 7
• 239000011777 magnesium Substances 0.000 description 7
• 239000003960 organic solvent Substances 0.000 description 7
• 125000005880 oxathiolanyl group Chemical group 0.000 description 7
• 125000004269 oxiran-2-yl group Chemical group [H]C1([H])OC1([H])* 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 6
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• 241000193388 Bacillus thuringiensis Species 0.000 description 6
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• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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• 230000009471 action Effects 0.000 description 6
• 150000001298 alcohols Chemical class 0.000 description 6
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
• 125000005108 alkenylthio group Chemical group 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
• 239000008187 granular material Substances 0.000 description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 description 6
• 229910052500 inorganic mineral Inorganic materials 0.000 description 6
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 6
• 235000010755 mineral Nutrition 0.000 description 6
• 125000005968 oxazolinyl group Chemical group 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 125000006513 pyridinyl methyl group Chemical group 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 6
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• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 5
• XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 5
• 241001663470 Contarinia <gall midge> Species 0.000 description 5
• 241000238631 Hexapoda Species 0.000 description 5
• 239000005799 Isopyrazam Substances 0.000 description 5
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• 125000003282 alkyl amino group Chemical group 0.000 description 5
• 229940097012 bacillus thuringiensis Drugs 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 230000008878 coupling Effects 0.000 description 5
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• 238000006476 reductive cyclization reaction Methods 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 229910052723 transition metal Inorganic materials 0.000 description 5
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 4
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• 241000995023 Empoasca Species 0.000 description 4
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• 241000244206 Nematoda Species 0.000 description 4
• 241000488557 Oligonychus Species 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• 241000562493 Pegomya Species 0.000 description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
• LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 description 4
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• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 4
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
• 125000004465 cycloalkenyloxy group Chemical group 0.000 description 4
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 4
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 4
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• 125000005114 heteroarylalkoxy group Chemical group 0.000 description 4
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