TW200918539A - Novel herbicides - Google Patents

Info

Publication number

TW200918539A

TW200918539A TW097124068A TW97124068A TW200918539A TW 200918539 A TW200918539 A TW 200918539A TW 097124068 A TW097124068 A TW 097124068A TW 97124068 A TW97124068 A TW 97124068A TW 200918539 A TW200918539 A TW 200918539A

Authority

TW

Taiwan

Prior art keywords

group

formula

compound

hydrogen

alkyl

Prior art date

2007-08-09

Links

• Espacenet
• Global Dossier
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• 239000004009 herbicide Substances 0.000 title claims abstract description 20
• 150000001875 compounds Chemical class 0.000 claims abstract description 840
• 229910052739 hydrogen Inorganic materials 0.000 claims description 533
• 239000001257 hydrogen Substances 0.000 claims description 531
• 150000002431 hydrogen Chemical group 0.000 claims description 326
• -1 cyclopropylethyl n-propyl Chemical group 0.000 claims description 264
• 125000000217 alkyl group Chemical group 0.000 claims description 257
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 159
• 239000000203 mixture Substances 0.000 claims description 116
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 104
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 94
• 125000003545 alkoxy group Chemical group 0.000 claims description 91
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 88
• 229910052736 halogen Inorganic materials 0.000 claims description 80
• 239000002585 base Substances 0.000 claims description 78
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
• 125000001072 heteroaryl group Chemical group 0.000 claims description 77
• 150000002367 halogens Chemical group 0.000 claims description 76
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 64
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 58
• 238000000034 method Methods 0.000 claims description 51
• 239000002904 solvent Substances 0.000 claims description 49
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 125000001424 substituent group Chemical group 0.000 claims description 43
• 125000001188 haloalkyl group Chemical group 0.000 claims description 41
• 125000003342 alkenyl group Chemical group 0.000 claims description 40
• 125000000304 alkynyl group Chemical group 0.000 claims description 40
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 38
• 239000002253 acid Substances 0.000 claims description 37
• 239000000460 chlorine Substances 0.000 claims description 35
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 34
• 239000003054 catalyst Substances 0.000 claims description 34
• 238000006243 chemical reaction Methods 0.000 claims description 32
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• 239000001301 oxygen Substances 0.000 claims description 26
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 24
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
• 229910052801 chlorine Inorganic materials 0.000 claims description 23
• 125000003282 alkyl amino group Chemical group 0.000 claims description 21
• 125000004414 alkyl thio group Chemical group 0.000 claims description 21
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 20
• 241000196324 Embryophyta Species 0.000 claims description 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
• 150000001412 amines Chemical class 0.000 claims description 17
• 230000002363 herbicidal effect Effects 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 16
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 15
• 239000011593 sulfur Substances 0.000 claims description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
• 238000009472 formulation Methods 0.000 claims description 14
• 150000002923 oximes Chemical class 0.000 claims description 13
• 229910052751 metal Inorganic materials 0.000 claims description 12
• 239000002184 metal Substances 0.000 claims description 12
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
• 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 9
• 125000003277 amino group Chemical group 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 8
• 244000025254 Cannabis sativa Species 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 229920002554 vinyl polymer Chemical group 0.000 claims description 7
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• PNDKCRDVVKJPKG-WHERJAGFSA-N cenicriviroc Chemical compound C1=CC(OCCOCCCC)=CC=C1C1=CC=C(N(CC(C)C)CCC\C(=C/2)C(=O)NC=3C=CC(=CC=3)[S@@](=O)CC=3N(C=NC=3)CCC)C\2=C1 PNDKCRDVVKJPKG-WHERJAGFSA-N 0.000 claims description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 150000001336 alkenes Chemical class 0.000 claims description 4
• 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000001624 naphthyl 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
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
• 239000007983 Tris buffer Substances 0.000 claims description 3
• 150000001340 alkali metals Chemical class 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• 125000004969 haloethyl group Chemical group 0.000 claims description 3
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
• 229920006395 saturated elastomer Polymers 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
• 229910052783 alkali metal Inorganic materials 0.000 claims description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
• 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
• KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 2
• JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004354 sulfur functional group Chemical group 0.000 claims description 2
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
• 150000001721 carbon Chemical group 0.000 claims 2
• 125000004970 halomethyl group Chemical group 0.000 claims 2
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical group FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
• 229910052684 Cerium Inorganic materials 0.000 claims 1
• 241000790917 Dioxys <bee> Species 0.000 claims 1
• 235000004279 alanine Nutrition 0.000 claims 1
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
• 239000003708 ampul Substances 0.000 claims 1
• 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
• 230000003796 beauty Effects 0.000 claims 1
• ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 1
• 125000005265 dialkylamine group Chemical group 0.000 claims 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
• 125000000879 imine group Chemical group 0.000 claims 1
• 125000000468 ketone group Chemical group 0.000 claims 1
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
• 244000045561 useful plants Species 0.000 claims 1
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 171
• XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 93
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
• 239000007789 gas Substances 0.000 description 46
• 239000000243 solution Substances 0.000 description 43
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• 238000002360 preparation method Methods 0.000 description 39
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
• 239000011541 reaction mixture Substances 0.000 description 32
• 235000019439 ethyl acetate Nutrition 0.000 description 30
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
• 239000004480 active ingredient Substances 0.000 description 28
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
• 125000001309 chloro group Chemical group Cl* 0.000 description 26
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
• 239000003921 oil Substances 0.000 description 23
• 235000019198 oils Nutrition 0.000 description 23
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• 239000003446 ligand Substances 0.000 description 20
• 239000003795 chemical substances by application Substances 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• 239000000654 additive Substances 0.000 description 17
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 17
• 229910052763 palladium Inorganic materials 0.000 description 17
• 150000003839 salts Chemical class 0.000 description 17
• 239000007787 solid Substances 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• 238000004440 column chromatography Methods 0.000 description 16
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 16
• 239000000499 gel Substances 0.000 description 15
• 239000000284 extract Substances 0.000 description 13
• 239000000052 vinegar Substances 0.000 description 13
• 235000021419 vinegar Nutrition 0.000 description 13
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 229910052707 ruthenium Inorganic materials 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
• 230000000996 additive effect Effects 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• 125000005843 halogen group Chemical group 0.000 description 11
• 238000006460 hydrolysis reaction Methods 0.000 description 11
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 11
• 230000009467 reduction Effects 0.000 description 11
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
• 230000007062 hydrolysis Effects 0.000 description 10
• 229910052740 iodine Inorganic materials 0.000 description 10
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
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• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
• 239000011630 iodine Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 229910052744 lithium Inorganic materials 0.000 description 9
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 8
• 101150041968 CDC13 gene Proteins 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 8
• 239000002671 adjuvant Substances 0.000 description 8
• 244000038559 crop plants Species 0.000 description 8
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
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• 238000003786 synthesis reaction Methods 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 7
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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
• 240000008042 Zea mays Species 0.000 description 7
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
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• 125000001246 bromo group Chemical group Br* 0.000 description 7
• 235000005822 corn Nutrition 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 150000002576 ketones Chemical class 0.000 description 7
• 239000011777 magnesium Substances 0.000 description 7
• 229910052749 magnesium Inorganic materials 0.000 description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 7
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• 238000003756 stirring Methods 0.000 description 7
• WRFWAYDBNCOWRA-UHFFFAOYSA-N 3,4-dichloro-1-(6-iodo-4-oxo-2-thiophen-2-ylquinazolin-3-yl)pyrrole-2,5-dione Chemical compound O=C1C(Cl)=C(Cl)C(=O)N1N1C(=O)C2=CC(I)=CC=C2N=C1C1=CC=CS1 WRFWAYDBNCOWRA-UHFFFAOYSA-N 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• 150000003973 alkyl amines Chemical class 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
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• 238000001816 cooling Methods 0.000 description 6
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 239000008187 granular material Substances 0.000 description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 6
• 239000012299 nitrogen atmosphere Substances 0.000 description 6
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