MXPA04010099A - Isoxazolinas sustituidas por 3 - heteroarilo. - Google Patents

Info

Publication number

MXPA04010099A

MXPA04010099A MXPA04010099A MXPA04010099A MXPA04010099A MX PA04010099 A MXPA04010099 A MX PA04010099A MX PA04010099 A MXPA04010099 A MX PA04010099A MX PA04010099 A MXPA04010099 A MX PA04010099A MX PA04010099 A MXPA04010099 A MX PA04010099A

Authority

MX

Mexico

Prior art keywords

alkyl

formula

methyl

alkoxy

heteroaryl

Prior art date

2002-04-25

Links

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• 239000004009 herbicide Substances 0.000 title claims description 5
• 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 1023
• 150000001875 compounds Chemical class 0.000 claims abstract description 172
• 239000001257 hydrogen Substances 0.000 claims abstract description 119
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 119
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 70
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 66
• 150000002547 isoxazolines Chemical class 0.000 claims abstract description 49
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
• 239000001301 oxygen Substances 0.000 claims abstract description 28
• 238000000034 method Methods 0.000 claims abstract description 25
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
• 150000003839 salts Chemical class 0.000 claims abstract description 18
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 4
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
• 239000013067 intermediate product Substances 0.000 claims abstract description 3
• 238000004519 manufacturing process Methods 0.000 claims abstract 4
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract 3
• 125000005605 benzo group Chemical group 0.000 claims abstract 3
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 81
• 125000001424 substituent group Chemical group 0.000 claims description 76
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 229910052717 sulfur Inorganic materials 0.000 claims description 31
• 125000004434 sulfur atom Chemical group 0.000 claims description 31
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 25
• 239000000047 product Substances 0.000 claims description 23
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
• 239000000203 mixture Substances 0.000 claims description 21
• 238000006243 chemical reaction Methods 0.000 claims description 18
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 150000002825 nitriles Chemical class 0.000 claims description 14
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000005002 aryl methyl group Chemical group 0.000 claims description 10
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 150000003254 radicals Chemical class 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• JHCKZGSCVJRFHY-UHFFFAOYSA-N 3-methyl-4,5-dihydro-1,2-oxazole Chemical class CC1=NOCC1 JHCKZGSCVJRFHY-UHFFFAOYSA-N 0.000 claims description 5
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
• 125000004453 alkoxycarbonyl 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
• 125000004438 haloalkoxy group Chemical group 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
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
• 238000002156 mixing Methods 0.000 claims description 4
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 3
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000004966 cyanoalkyl 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
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
• 239000003223 protective agent Substances 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
• 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• 125000004103 aminoalkyl group Chemical group 0.000 claims 1
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 1
• 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
• 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims 1
• 125000000232 haloalkynyl group Chemical group 0.000 claims 1
• 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
• 125000003884 phenylalkyl group Chemical group 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 abstract description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
• 150000002431 hydrogen Chemical class 0.000 description 67
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 61
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 42
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 22
• 125000003971 isoxazolinyl group Chemical group 0.000 description 20
• 241000196324 Embryophyta Species 0.000 description 18
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• 229910052757 nitrogen Inorganic materials 0.000 description 16
• PHVFVPURCHVDBP-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazol-5-ylmethanol Chemical compound OCC1CC=NO1 PHVFVPURCHVDBP-UHFFFAOYSA-N 0.000 description 15
• 125000005842 heteroatom Chemical group 0.000 description 15
• 230000002363 herbicidal effect Effects 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
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 239000013543 active substance Substances 0.000 description 11
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 11
• 239000004480 active ingredient Substances 0.000 description 10
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
• 230000008569 process Effects 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
• 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
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 125000001246 bromo group Chemical group Br* 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 8
• 125000001309 chloro group Chemical group Cl* 0.000 description 8
• 125000001153 fluoro group Chemical group F* 0.000 description 8
• 125000002346 iodo group Chemical group I* 0.000 description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• 125000001624 naphthyl group Chemical group 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
• 239000011575 calcium Substances 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
• 230000012010 growth Effects 0.000 description 6
• 125000000842 isoxazolyl group Chemical group 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 238000005507 spraying 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
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• 239000012141 concentrate Substances 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 125000002541 furyl group Chemical group 0.000 description 5
• 125000005843 halogen group Chemical group 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 239000011630 iodine Substances 0.000 description 5
• 125000001786 isothiazolyl group Chemical group 0.000 description 5
• 239000003446 ligand Substances 0.000 description 5
• 125000002971 oxazolyl group Chemical group 0.000 description 5
• 125000003373 pyrazinyl group Chemical group 0.000 description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 239000007787 solid Substances 0.000 description 5
• 125000000335 thiazolyl group Chemical group 0.000 description 5
• 238000011282 treatment Methods 0.000 description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 4
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 4
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 4
• IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-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
• 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
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 244000038559 crop plants Species 0.000 description 4
• 125000004663 dialkyl amino group Chemical group 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• 230000000269 nucleophilic effect Effects 0.000 description 4
• CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 4
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 3
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 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
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
• 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
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 240000005498 Setaria italica Species 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
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• 150000001340 alkali metals 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
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
• 230000035784 germination Effects 0.000 description 3
• 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 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 238000002955 isolation Methods 0.000 description 3
• 229920005610 lignin Polymers 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
• 235000010446 mineral oil Nutrition 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 239000006072 paste Substances 0.000 description 3
• 229920003023 plastic Polymers 0.000 description 3
• 238000012545 processing Methods 0.000 description 3
• 159000000000 sodium salts Chemical class 0.000 description 3
• 241000894007 species Species 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
• 238000005160 1H NMR spectroscopy Methods 0.000 description 2
• PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 2
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• 239000005995 Aluminium silicate Substances 0.000 description 2
• 235000021533 Beta vulgaris Nutrition 0.000 description 2
• 241000335053 Beta vulgaris Species 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 235000010469 Glycine max Nutrition 0.000 description 2
• 244000068988 Glycine max Species 0.000 description 2
• 244000299507 Gossypium hirsutum Species 0.000 description 2
• 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 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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