CA2481793A1 - 3-heteroaryl substituted 5-methyloxymethyl isoxazolines used as herbicides - Google Patents

Info

Publication number

CA2481793A1

CA2481793A1 CA002481793A CA2481793A CA2481793A1 CA 2481793 A1 CA2481793 A1 CA 2481793A1 CA 002481793 A CA002481793 A CA 002481793A CA 2481793 A CA2481793 A CA 2481793A CA 2481793 A1 CA2481793 A1 CA 2481793A1

Authority

CA

Canada

Prior art keywords

alkyl

formula

alkoxy

methyl

amino

Prior art date

2002-04-25

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000004009 herbicide Substances 0.000 title claims description 6
• AMCUCJRYPFDOCU-UHFFFAOYSA-N 5-(methoxymethyl)-4,5-dihydro-1,2-oxazole Chemical class COCC1CC=NO1 AMCUCJRYPFDOCU-UHFFFAOYSA-N 0.000 title 1
• -1 benzo[1,3]dioxolanyl Chemical group 0.000 claims abstract description 1303
• 239000001257 hydrogen Substances 0.000 claims abstract description 118
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 118
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 66
• 150000002547 isoxazolines Chemical class 0.000 claims abstract description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 43
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
• 239000001301 oxygen Substances 0.000 claims abstract description 31
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 26
• 238000000034 method Methods 0.000 claims abstract description 23
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 10
• 238000004519 manufacturing process Methods 0.000 claims abstract description 5
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000005605 benzo group Chemical group 0.000 claims abstract description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 125
• 125000001424 substituent group Chemical group 0.000 claims description 83
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 81
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 69
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 67
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 55
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 49
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 239000000203 mixture Substances 0.000 claims description 35
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 31
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 125000004434 sulfur atom Chemical group 0.000 claims description 28
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 23
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 14
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
• 150000002825 nitriles Chemical class 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000005002 aryl methyl group Chemical group 0.000 claims description 11
• JHCKZGSCVJRFHY-UHFFFAOYSA-N 3-methyl-4,5-dihydro-1,2-oxazole Chemical class CC1=NOCC1 JHCKZGSCVJRFHY-UHFFFAOYSA-N 0.000 claims description 8
• 150000003254 radicals Chemical class 0.000 claims description 8
• 125000006772 (C1-C6) haloalkylsulfonyloxy group Chemical group 0.000 claims description 5
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
• 239000011814 protection agent Substances 0.000 claims description 4
• 238000002156 mixing Methods 0.000 claims description 3
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
• DIYXRDINNSPDFJ-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazol-5-ylmethanol Chemical compound OCC1CN=CO1 DIYXRDINNSPDFJ-UHFFFAOYSA-N 0.000 claims 2
• 150000001875 compounds Chemical class 0.000 abstract description 191
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 8
• 239000003795 chemical substances by application Substances 0.000 abstract description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 5
• 125000000217 alkyl group Chemical group 0.000 abstract description 5
• 125000003226 pyrazolyl group Chemical group 0.000 abstract description 4
• 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
• 125000001544 thienyl group Chemical group 0.000 abstract description 2
• 239000013067 intermediate product Substances 0.000 abstract 1
• 125000003107 substituted aryl group Chemical group 0.000 abstract 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 133
• 150000002431 hydrogen Chemical class 0.000 description 62
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 43
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 42
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 27
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 27
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
• 239000000460 chlorine Substances 0.000 description 21
• 229910052757 nitrogen Inorganic materials 0.000 description 21
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 20
• 125000003971 isoxazolinyl group Chemical group 0.000 description 20
• PHVFVPURCHVDBP-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazol-5-ylmethanol Chemical compound OCC1CC=NO1 PHVFVPURCHVDBP-UHFFFAOYSA-N 0.000 description 18
• 229910052794 bromium Inorganic materials 0.000 description 18
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
• 125000005842 heteroatom Chemical group 0.000 description 17
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
• 241000196324 Embryophyta Species 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 16
• 229910052801 chlorine Inorganic materials 0.000 description 16
• 125000004076 pyridyl group Chemical group 0.000 description 14
• 229910052799 carbon Inorganic materials 0.000 description 13
• 230000002363 herbicidal effect Effects 0.000 description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
• 229910052731 fluorine Inorganic materials 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 11
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• 150000001721 carbon Chemical group 0.000 description 10
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
• 239000011737 fluorine Substances 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 125000001153 fluoro group Chemical group F* 0.000 description 8
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• 229910052740 iodine Inorganic materials 0.000 description 7
• 125000000842 isoxazolyl group Chemical group 0.000 description 7
• 125000001624 naphthyl group Chemical group 0.000 description 7
• 125000000335 thiazolyl group Chemical group 0.000 description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
• 239000004359 castor oil Substances 0.000 description 6
• 235000019438 castor oil Nutrition 0.000 description 6
• 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 6
• 239000011630 iodine Substances 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 125000003373 pyrazinyl group Chemical group 0.000 description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 5
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 5
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 5
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 5
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 5
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 5
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 5
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
• 239000012141 concentrate Substances 0.000 description 5
• 244000038559 crop plants Species 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 125000002541 furyl group Chemical group 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 125000001786 isothiazolyl group Chemical group 0.000 description 5
• 125000002971 oxazolyl group Chemical group 0.000 description 5
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
• 125000000168 pyrrolyl group Chemical group 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 239000000243 solution Substances 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 238000011282 treatment Methods 0.000 description 5
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 5
• IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
• 240000005498 Setaria italica Species 0.000 description 4
• 239000013543 active substance Substances 0.000 description 4
• 150000001340 alkali metals Chemical class 0.000 description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 125000004414 alkyl thio group Chemical group 0.000 description 4
• 125000004429 atom Chemical group 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 125000004663 dialkyl amino group Chemical group 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 235000012054 meals Nutrition 0.000 description 4
• CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
• 229920000151 polyglycol Polymers 0.000 description 4
• 239000010695 polyglycol Substances 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
• FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 3
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• 125000004564 2,3-dihydrobenzofuran-2-yl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 3
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 3
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
• 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 3
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 3
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 235000007226 Setaria italica Nutrition 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 230000003213 activating effect Effects 0.000 description 3
• 125000003282 alkyl amino group Chemical group 0.000 description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
• 150000004808 allyl alcohols Chemical class 0.000 description 3
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
• 150000001450 anions Chemical class 0.000 description 3
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 235000013877 carbamide Nutrition 0.000 description 3
• 125000004432 carbon atom Chemical group C* 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 150000001768 cations Chemical class 0.000 description 3
• 230000006378 damage Effects 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
• 238000002955 isolation Methods 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
• 239000002480 mineral oil Substances 0.000 description 3
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