BRPI0814926B1 - composto de ciclopentanodiona herbicidamente ativo, seu processo de preparação, sua composição herbicida e método para controlar gramas em colheitas de plantas úteis - Google Patents

Info

Publication number

BRPI0814926B1

BRPI0814926B1 BRPI0814926A BRPI0814926A BRPI0814926B1 BR PI0814926 B1 BRPI0814926 B1 BR PI0814926B1 BR PI0814926 A BRPI0814926 A BR PI0814926A BR PI0814926 A BRPI0814926 A BR PI0814926A BR PI0814926 B1 BRPI0814926 B1 BR PI0814926B1

Authority

BR

Brazil

Prior art keywords

formula

hydrogen

compound

alkyl

covers

Prior art date

2007-08-09

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• 239000000203 mixture Substances 0.000 title claims description 123
• 238000000034 method Methods 0.000 title claims description 62
• 238000002360 preparation method Methods 0.000 title claims description 43
• 230000002363 herbicidal effect Effects 0.000 title claims description 20
• 241000209504 Poaceae Species 0.000 title claims 2
• -1 cyclopentanedione compound Chemical class 0.000 title description 145
• 150000001875 compounds Chemical class 0.000 claims description 665
• 229910052739 hydrogen Inorganic materials 0.000 claims description 584
• 239000001257 hydrogen Substances 0.000 claims description 583
• 150000002431 hydrogen Chemical class 0.000 claims description 368
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 194
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 125
• 125000000217 alkyl group Chemical group 0.000 claims description 99
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 92
• 229910052736 halogen Inorganic materials 0.000 claims description 78
• 150000002367 halogens Chemical class 0.000 claims description 75
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
• 239000002904 solvent Substances 0.000 claims description 48
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• 125000001188 haloalkyl group Chemical group 0.000 claims description 33
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 239000003054 catalyst Substances 0.000 claims description 24
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 239000004009 herbicide Substances 0.000 claims description 20
• 241000196324 Embryophyta Species 0.000 claims description 19
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
• 238000009472 formulation Methods 0.000 claims description 19
• 230000001012 protector Effects 0.000 claims description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 14
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
• 229910052740 iodine Inorganic materials 0.000 claims description 10
• 238000002156 mixing Methods 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 239000002841 Lewis acid Substances 0.000 claims 1
• 150000007517 lewis acids Chemical class 0.000 claims 1
• XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 94
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 70
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
• 239000000243 solution Substances 0.000 description 49
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 41
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 40
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 37
• 239000011541 reaction mixture Substances 0.000 description 36
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
• 239000002585 base Substances 0.000 description 33
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 32
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 32
• 239000000460 chlorine Substances 0.000 description 31
• 229910052801 chlorine Inorganic materials 0.000 description 31
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
• 125000001309 chloro group Chemical group Cl* 0.000 description 30
• 239000004480 active ingredient Substances 0.000 description 29
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• 125000003118 aryl group Chemical group 0.000 description 27
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 27
• 239000003921 oil Substances 0.000 description 27
• 235000019198 oils Nutrition 0.000 description 27
• 125000000753 cycloalkyl group Chemical group 0.000 description 26
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 26
• 239000000706 filtrate Substances 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 24
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 24
• 239000007787 solid Substances 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 21
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 20
• 229910052717 sulfur Inorganic materials 0.000 description 19
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• 125000000623 heterocyclic group Chemical group 0.000 description 18
• 238000010898 silica gel chromatography Methods 0.000 description 18
• 239000002253 acid Substances 0.000 description 17
• 239000000654 additive Substances 0.000 description 17
• 150000003839 salts Chemical class 0.000 description 16
• ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 16
• 238000007792 addition Methods 0.000 description 15
• 125000003342 alkenyl group Chemical group 0.000 description 14
• 229910052757 nitrogen Inorganic materials 0.000 description 14
• 229910052763 palladium Inorganic materials 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 13
• 125000000304 alkynyl group Chemical group 0.000 description 13
• 239000003153 chemical reaction reagent Substances 0.000 description 13
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 12
• 230000015572 biosynthetic process Effects 0.000 description 12
• NUOXSJGIRWCWNR-UHFFFAOYSA-N decane-3,5-dione Chemical compound CCCCCC(=O)CC(=O)CC NUOXSJGIRWCWNR-UHFFFAOYSA-N 0.000 description 12
• 239000000284 extract Substances 0.000 description 12
• 229920002554 vinyl polymer Chemical group 0.000 description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
• 239000005909 Kieselgur Substances 0.000 description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
• 239000011593 sulfur Substances 0.000 description 11
• 239000004094 surface-active agent Substances 0.000 description 11
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 10
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 10
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 10
• 239000011230 binding agent Substances 0.000 description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
• 229910052794 bromium Inorganic materials 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 125000005842 heteroatom Chemical group 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 239000013543 active substance Substances 0.000 description 9
• 239000002671 adjuvant Substances 0.000 description 9
• 150000001543 aryl boronic acids Chemical class 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• 239000011630 iodine Substances 0.000 description 9
• 229910052744 lithium Inorganic materials 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 8
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
• 230000000996 additive effect Effects 0.000 description 8
• 125000003282 alkyl amino group Chemical group 0.000 description 8
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 8
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 230000009467 reduction Effects 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 239000003981 vehicle Substances 0.000 description 8
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 7
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 7
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• 239000002202 Polyethylene glycol Substances 0.000 description 7
• 240000008042 Zea mays Species 0.000 description 7
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
• 244000038559 crop plants Species 0.000 description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 description 7
• ZYPBKYCUPQQMKH-UHFFFAOYSA-N dec-8-ene-3,5-dione Chemical compound CCC(=O)CC(=O)CCC=CC ZYPBKYCUPQQMKH-UHFFFAOYSA-N 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 125000005241 heteroarylamino group Chemical group 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• 239000012299 nitrogen atmosphere Substances 0.000 description 7
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 7
• 229920001223 polyethylene glycol Polymers 0.000 description 7
• 239000007921 spray Substances 0.000 description 7
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 6
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 6
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• 229920000742 Cotton Polymers 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• 150000001336 alkenes Chemical class 0.000 description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
• 238000013459 approach Methods 0.000 description 6
• 150000001502 aryl halides Chemical class 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• 125000001153 fluoro group Chemical group F* 0.000 description 6
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 description 6
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
• 230000002378 acidificating effect Effects 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 5
• 239000012141 concentrate Substances 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 239000006184 cosolvent Substances 0.000 description 5
• 125000005240 diheteroarylamino group Chemical group 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 125000005843 halogen group Chemical group 0.000 description 5
• 230000026030 halogenation Effects 0.000 description 5
• 238000005658 halogenation reaction Methods 0.000 description 5
• 150000002576 ketones Chemical class 0.000 description 5
• 239000011968 lewis acid catalyst Substances 0.000 description 5
• 235000009973 maize Nutrition 0.000 description 5
• UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 5
• 239000003094 microcapsule Substances 0.000 description 5
• 239000002480 mineral oil Substances 0.000 description 5
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
• WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 5
• 235000015112 vegetable and seed oil Nutrition 0.000 description 5
• 239000008158 vegetable oil Substances 0.000 description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
• 238000005406 washing Methods 0.000 description 5
• 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
• ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
• SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• 229910015900 BF3 Inorganic materials 0.000 description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
• 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 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
• 229910052783 alkali metal Inorganic materials 0.000 description 4
• 229910000272 alkali metal oxide Inorganic materials 0.000 description 4
• 150000001340 alkali metals Chemical class 0.000 description 4
• 125000005907 alkyl ester group Chemical group 0.000 description 4
• 150000001350 alkyl halides Chemical class 0.000 description 4
• 125000005103 alkyl silyl group Chemical group 0.000 description 4
• 125000004414 alkyl thio group Chemical group 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 125000001246 bromo group Chemical group Br* 0.000 description 4
• 229910052799 carbon Inorganic materials 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 238000005859 coupling reaction Methods 0.000 description 4
• 238000006880 cross-coupling reaction Methods 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
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