KR20050111648A - 3-헤테로시클릴로 치환된 벤조일 유도체 - Google Patents

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Publication number

KR20050111648A

KR20050111648A KR1020057020499A KR20057020499A KR20050111648A KR 20050111648 A KR20050111648 A KR 20050111648A KR 1020057020499 A KR1020057020499 A KR 1020057020499A KR 20057020499 A KR20057020499 A KR 20057020499A KR 20050111648 A KR20050111648 A KR 20050111648A

Authority

KR

South Korea

Prior art keywords

alkyl

hydrogen

formula

substituted

alkoxy

Prior art date

1997-01-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

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• 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 title claims abstract description 78
• -1 alkoxy halide Chemical class 0.000 claims abstract description 688
• 239000001257 hydrogen Substances 0.000 claims abstract description 380
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 380
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 114
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 92
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 73
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 64
• 150000002367 halogens Chemical class 0.000 claims abstract description 64
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 46
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
• 238000000034 method Methods 0.000 claims abstract description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 25
• 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims abstract description 18
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 14
• 238000002360 preparation method Methods 0.000 claims abstract description 7
• 150000001875 compounds Chemical class 0.000 claims description 596
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 283
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 173
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 123
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 96
• 239000000203 mixture Substances 0.000 claims description 56
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 49
• 239000001301 oxygen Substances 0.000 claims description 49
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 44
• 229910052757 nitrogen Chemical group 0.000 claims description 35
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 28
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 27
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 26
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 25
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 24
• 241000196324 Embryophyta Species 0.000 claims description 23
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 20
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 15
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 238000006243 chemical reaction Methods 0.000 claims description 11
• 150000001558 benzoic acid derivatives Chemical group 0.000 claims description 10
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 8
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 229910021386 carbon form Inorganic materials 0.000 claims description 6
• IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 5
• CPLDIWZIQNXJME-UHFFFAOYSA-N CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2CC(ON=2)C#N)=C1Cl Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2CC(ON=2)C#N)=C1Cl CPLDIWZIQNXJME-UHFFFAOYSA-N 0.000 claims description 5
• PXVQWKUYBMZLRB-UHFFFAOYSA-N CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2SCCN=2)=C1Cl Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2SCCN=2)=C1Cl PXVQWKUYBMZLRB-UHFFFAOYSA-N 0.000 claims description 5
• IUCXCDBYRBQAJD-UHFFFAOYSA-N CCN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CCN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O IUCXCDBYRBQAJD-UHFFFAOYSA-N 0.000 claims description 5
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
• 239000003054 catalyst Substances 0.000 claims description 5
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
• JHRWYMSHFLHBCR-UHFFFAOYSA-N CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2CCON=2)=C1Cl Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(S(C)(=O)=O)C(C=2CCON=2)=C1Cl JHRWYMSHFLHBCR-UHFFFAOYSA-N 0.000 claims description 4
• PYKSVIGIFCAYLQ-UHFFFAOYSA-N Cc1nn(C)c(O)c1C(=O)c1ccc(c(C2=NC(=O)C(=O)S2)c1Cl)S(C)(=O)=O Chemical compound Cc1nn(C)c(O)c1C(=O)c1ccc(c(C2=NC(=O)C(=O)S2)c1Cl)S(C)(=O)=O PYKSVIGIFCAYLQ-UHFFFAOYSA-N 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• CMHAHZIWNCFHFL-UHFFFAOYSA-N methyl 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=2CCON=2)=C1Cl CMHAHZIWNCFHFL-UHFFFAOYSA-N 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• FCODLBLEKSFOLV-UHFFFAOYSA-N CN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O FCODLBLEKSFOLV-UHFFFAOYSA-N 0.000 claims description 3
• 238000009472 formulation Methods 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 235000012054 meals Nutrition 0.000 claims description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• OSEPKGABXAAEAW-UHFFFAOYSA-N COC(=O)C1=C(C(=C(C=C1)S(=O)(=O)C)N2CCCO2)Cl Chemical compound COC(=O)C1=C(C(=C(C=C1)S(=O)(=O)C)N2CCCO2)Cl OSEPKGABXAAEAW-UHFFFAOYSA-N 0.000 claims description 2
• 150000007942 carboxylates Chemical class 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
• ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
• JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims 1
• IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 claims 1
• 125000003545 alkoxy group Chemical group 0.000 abstract description 6
• 239000004009 herbicide Substances 0.000 abstract description 6
• 125000004414 alkyl thio group Chemical group 0.000 abstract description 4
• 239000000126 substance Substances 0.000 abstract description 3
• 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
• 239000003814 drug Substances 0.000 abstract 2
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 abstract 1
• 150000001350 alkyl halides Chemical class 0.000 abstract 1
• 125000005265 dialkylamine group Chemical group 0.000 abstract 1
• 229940079593 drug Drugs 0.000 abstract 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
• 239000013067 intermediate product Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 54
• 239000000460 chlorine Substances 0.000 description 37
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 36
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
• 229910052801 chlorine Inorganic materials 0.000 description 35
• 239000000243 solution Substances 0.000 description 34
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 32
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 239000004480 active ingredient Substances 0.000 description 23
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
• 239000002904 solvent Substances 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• 229910052794 bromium Inorganic materials 0.000 description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
• 230000002363 herbicidal effect Effects 0.000 description 17
• 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 16
• 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• 239000002585 base Substances 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 13
• 238000002844 melting Methods 0.000 description 12
• 230000008018 melting Effects 0.000 description 12
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 12
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
• 239000012074 organic phase Substances 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• 239000011737 fluorine Substances 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• 150000002825 nitriles Chemical class 0.000 description 9
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-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
• 239000002253 acid Substances 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 8
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• 235000010233 benzoic acid Nutrition 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• 229910052727 yttrium Inorganic materials 0.000 description 7
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• 239000005711 Benzoic acid Substances 0.000 description 6
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 239000012141 concentrate Substances 0.000 description 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
• 125000001153 fluoro group Chemical group F* 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
• 240000008042 Zea mays Species 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
• 229910000288 alkali metal carbonate Chemical group 0.000 description 5
• 150000008041 alkali metal carbonates Chemical group 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 239000004359 castor oil Substances 0.000 description 5
• 235000019438 castor oil Nutrition 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
• 239000011630 iodine Substances 0.000 description 5
• GTXHAHDFJJTAKY-UHFFFAOYSA-N methyl 3-carbonochloridoyl-2-chloro-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C(Cl)=O)=C1Cl GTXHAHDFJJTAKY-UHFFFAOYSA-N 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 239000001632 sodium acetate Substances 0.000 description 5
• 235000017281 sodium acetate Nutrition 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• JURLTYXSZFLINT-UHFFFAOYSA-N 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=C(C(Cl)=O)C(Cl)=C1C1=NOCC1 JURLTYXSZFLINT-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
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