HRP20041120A2 - 3-heteroaryl substituted 5-methyloxymethyl-isoxazolines used as herbicides - Google Patents

Info

Publication number

HRP20041120A2

HRP20041120A2 HR20041120A HRP20041120A HRP20041120A2 HR P20041120 A2 HRP20041120 A2 HR P20041120A2 HR 20041120 A HR20041120 A HR 20041120A HR P20041120 A HRP20041120 A HR P20041120A HR P20041120 A2 HRP20041120 A2 HR P20041120A2

Authority

HR

Croatia

Prior art keywords

alkyl

formula

alkoxy

methyl

haloalkyl

Prior art date

2002-04-25

Links

• Espacenet
• Global Dossier
• Discuss

• 239000004009 herbicide Substances 0.000 title claims description 7
• 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 854
• 239000001257 hydrogen Substances 0.000 claims abstract description 114
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 114
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 68
• 150000002547 isoxazolines Chemical class 0.000 claims abstract description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 44
• 239000000203 mixture Substances 0.000 claims abstract description 33
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 32
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 31
• 238000000034 method Methods 0.000 claims abstract description 28
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 25
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
• 239000001301 oxygen Substances 0.000 claims abstract description 22
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract description 20
• 150000003839 salts Chemical class 0.000 claims abstract description 19
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 17
• 238000002360 preparation method Methods 0.000 claims abstract description 16
• 230000008569 process Effects 0.000 claims abstract description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 4
• 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
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
• 239000000126 substance Substances 0.000 claims description 160
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 134
• 125000001424 substituent group Chemical group 0.000 claims description 84
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 72
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
• 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
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 20
• 238000006243 chemical reaction Methods 0.000 claims description 20
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
• 125000003601 C2-C6 alkynyl group Chemical group 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 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 150000002825 nitriles Chemical class 0.000 claims description 16
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
• 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
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 8
• 239000003153 chemical reaction reagent Substances 0.000 claims description 8
• 150000003254 radicals Chemical class 0.000 claims description 8
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 230000000269 nucleophilic effect Effects 0.000 claims description 7
• 125000006772 (C1-C6) haloalkylsulfonyloxy group Chemical group 0.000 claims description 6
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
• 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
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
• 238000002156 mixing Methods 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 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
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract description 8
• 239000000543 intermediate Substances 0.000 abstract description 6
• 125000000217 alkyl group Chemical group 0.000 abstract description 5
• 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
• 125000003107 substituted aryl group Chemical group 0.000 abstract 1
• 125000004093 cyano group Chemical group *C#N 0.000 description 72
• 150000002431 hydrogen Chemical class 0.000 description 56
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 54
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 46
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 43
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 43
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 41
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 33
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 31
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 29
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 28
• 239000013543 active substance Substances 0.000 description 27
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
• 241000196324 Embryophyta Species 0.000 description 22
• 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 group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
• 239000000460 chlorine Chemical group 0.000 description 17
• 229910052801 chlorine Inorganic materials 0.000 description 17
• 125000005842 heteroatom Chemical group 0.000 description 17
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 15
• 125000004076 pyridyl group Chemical group 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 13
• 125000004430 oxygen atom Chemical group O* 0.000 description 13
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 12
• 125000002373 5 membered heterocyclic 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
• 230000002363 herbicidal effect Effects 0.000 description 12
• 230000008901 benefit Effects 0.000 description 11
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 11
• 229910052731 fluorine Inorganic materials 0.000 description 11
• 229910052799 carbon Inorganic materials 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
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 10
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000004615 ingredient 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
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• 125000001153 fluoro group Chemical group F* 0.000 description 7
• 125000000842 isoxazolyl group Chemical group 0.000 description 7
• 125000001624 naphthyl group Chemical group 0.000 description 7
• 239000000047 product Substances 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 group [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
• 239000002253 acid Substances 0.000 description 6
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
• 239000002585 base 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
• 239000011630 iodine Chemical group 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 125000003373 pyrazinyl group Chemical group 0.000 description 6
• 125000000714 pyrimidinyl group Chemical group 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
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 5
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• 239000012141 concentrate Substances 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
• 239000008187 granular material Substances 0.000 description 5
• 125000002883 imidazolyl group Chemical group 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 group 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
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 150000001340 alkali metals Chemical class 0.000 description 4
• 150000001342 alkaline earth metals Chemical class 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
• 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
• 238000005507 spraying Methods 0.000 description 4
• 239000011593 sulfur 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
• 125000004741 (C1-C6) haloalkylsulfonyl 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
• 125000006113 1,2-dimethylbutyl sulfinyl group Chemical group 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• 125000006140 3-methylpentyl sulfonyl group Chemical group 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
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
• 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
• 230000009471 action 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
• 150000001450 anions 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
• 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
• 238000002474 experimental method Methods 0.000 description 3
• 235000013312 flour Nutrition 0.000 description 3
• 230000035784 germination Effects 0.000 description 3
• 238000002955 isolation Methods 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 239000007788 liquid Substances 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
• 239000006072 paste Substances 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
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
• 125000006127 1-methylpropyl sulfonyl group Chemical group 0.000 description 2
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
• NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-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
• 125000006139 2-methylpentyl sulfonyl group Chemical group 0.000 description 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=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
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-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
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
• 235000010469 Glycine max Nutrition 0.000 description 2
• 244000068988 Glycine max Species 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
• 229910002651 NO3 Inorganic materials 0.000 description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 240000006394 Sorghum bicolor Species 0.000 description 2
• 244000098338 Triticum aestivum Species 0.000 description 2
• 240000008042 Zea mays Species 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 230000003213 activating effect Effects 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
• 125000002877 alkyl aryl group Chemical group 0.000 description 2
• 150000005215 alkyl ethers Chemical class 0.000 description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
• 235000012211 aluminium silicate Nutrition 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
• 150000001555 benzenes Chemical class 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 description 2
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
• OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 235000013339 cereals Nutrition 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
• 239000002270 dispersing agent Substances 0.000 description 2
• 238000009826 distribution Methods 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 150000002191 fatty alcohols Chemical class 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• 150000004820 halides Chemical class 0.000 description 2
• 150000008282 halocarbons Chemical class 0.000 description 2
• 230000002140 halogenating effect Effects 0.000 description 2
• 239000003906 humectant Substances 0.000 description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 description 2
• 150000002500 ions Chemical class 0.000 description 2
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
• 239000011707 mineral Substances 0.000 description 2
• 235000010755 mineral Nutrition 0.000 description 2
• 235000010446 mineral oil Nutrition 0.000 description 2
• 150000002790 naphthalenes Chemical class 0.000 description 2
• 239000012074 organic phase Substances 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• 150000002923 oximes Chemical class 0.000 description 2
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
• 229920003023 plastic Polymers 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 230000001681 protective effect Effects 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 239000000377 silicon dioxide Substances 0.000 description 2
• 159000000000 sodium salts Chemical class 0.000 description 2
• 239000002689 soil Substances 0.000 description 2
• 239000000758 substrate Substances 0.000 description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 235000013311 vegetables Nutrition 0.000 description 2
• 239000002699 waste material Substances 0.000 description 2
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• 125000006112 1, 1-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000006079 1,1,2-trimethyl-2-propenyl group Chemical group 0.000 description 1
• 125000006150 1,1,2-trimethylpropyl sulfonyl group Chemical group 0.000 description 1
• 125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
• 125000006060 1,1-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000006142 1,1-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000006098 1,1-dimethylethyl sulfinyl group Chemical group 0.000 description 1
• 125000004711 1,1-dimethylethylthio group Chemical group CC(C)(S*)C 0.000 description 1
• 125000006103 1,1-dimethylpropyl sulfinyl group Chemical group 0.000 description 1
• 125000006133 1,1-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
• 125000006121 1,2,2-trimethylpropyl sulfinyl group Chemical group 0.000 description 1
• 125000006151 1,2,2-trimethylpropyl sulfonyl group Chemical group 0.000 description 1
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
• 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
• 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
• 125000006061 1,2-dimethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006034 1,2-dimethyl-1-propenyl group Chemical group 0.000 description 1
• 125000006062 1,2-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
• 125000006063 1,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
• 125000006143 1,2-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000006104 1,2-dimethylpropyl sulfinyl group Chemical group 0.000 description 1
• 125000006134 1,2-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
• 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
• 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
• 125000006064 1,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006066 1,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000006114 1,3-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000006144 1,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical class OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
• 125000006073 1-ethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006080 1-ethyl-1-methyl-2-propenyl group Chemical group 0.000 description 1
• 125000006122 1-ethyl-1-methylpropyl sulfinyl group Chemical group 0.000 description 1
• 125000006152 1-ethyl-1-methylpropyl sulfonyl group Chemical group 0.000 description 1
• 125000006036 1-ethyl-1-propenyl group Chemical group 0.000 description 1
• 125000006074 1-ethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006081 1-ethyl-2-methyl-1-propenyl group Chemical group 0.000 description 1
• 125000006082 1-ethyl-2-methyl-2-propenyl group Chemical group 0.000 description 1
• 125000006123 1-ethyl-2-methylpropyl sulfinyl group Chemical group 0.000 description 1
• 125000006153 1-ethyl-2-methylpropyl sulfonyl group Chemical group 0.000 description 1
• 125000004736 1-ethyl-2-methylpropylthio group Chemical group C(C)C(C(C)C)S* 0.000 description 1
• 125000006037 1-ethyl-2-propenyl group Chemical group 0.000 description 1
• 125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
• 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000006148 1-ethylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000006106 1-ethylpropyl sulfinyl group Chemical group 0.000 description 1
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
• 125000006039 1-hexenyl group Chemical group 0.000 description 1
• 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
• 125000006044 1-methyl-1-pentenyl group Chemical group 0.000 description 1
• 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
• 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
• 125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
• 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
• 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
• 125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 1
• 125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
• 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
• 125000006100 1-methylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000006130 1-methylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000006094 1-methylethyl sulfinyl group Chemical group 0.000 description 1
• 125000006138 1-methylpentyl sulfonyl group Chemical group 0.000 description 1
• 125000006096 1-methylpropyl sulfinyl group Chemical group 0.000 description 1
• 125000006023 1-pentenyl group Chemical group 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• 125000004338 2,2,3-trimethylbutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
• 125000006067 2,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000006115 2,2-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000003562 2,2-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000006105 2,2-dimethylpropyl sulfinyl group Chemical group 0.000 description 1
• LMCBYQIBQXKCLN-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid;naphthalene Chemical compound C1=CC=CC2=CC=CC=C21.C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 LMCBYQIBQXKCLN-UHFFFAOYSA-N 0.000 description 1
• SCLSKOXHUCZTEI-UHFFFAOYSA-N 2,3-dihydropyrazol-1-yl Chemical group C1C=[C]N=N1 SCLSKOXHUCZTEI-UHFFFAOYSA-N 0.000 description 1
• 125000006068 2,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006070 2,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
• 125000006116 2,3-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
• MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
• 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
• PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
• KLGTXQOZQXTQPQ-UHFFFAOYSA-N 2-benzyl-1,2-oxazolidin-3-one Chemical class O=C1CCON1CC1=CC=CC=C1 KLGTXQOZQXTQPQ-UHFFFAOYSA-N 0.000 description 1
• ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
• 125000005999 2-bromoethyl group Chemical group 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
• 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
• VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
• KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
• 125000006076 2-ethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006077 2-ethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006078 2-ethyl-3-butenyl group Chemical group 0.000 description 1
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000006149 2-ethylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000006040 2-hexenyl group Chemical group 0.000 description 1
• 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 1
• 125000006045 2-methyl-1-pentenyl group Chemical group 0.000 description 1
• 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
• 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
• 125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 1
• 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
• 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
• 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
• 125000006056 2-methyl-4-pentenyl group Chemical group 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000006101 2-methylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000006131 2-methylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000005916 2-methylpentyl group Chemical group 0.000 description 1
• 125000006109 2-methylpentyl sulfinyl group Chemical group 0.000 description 1
• BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
• 125000006097 2-methylpropyl sulfinyl group Chemical group 0.000 description 1
• 125000006128 2-methylpropyl sulfonyl group Chemical group 0.000 description 1
• 125000006024 2-pentenyl group Chemical group 0.000 description 1
• QBGQIMOGHUXVKB-UHFFFAOYSA-N 2-phenyl-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical class O=C1C(CCCC2)=C2C(=O)N1C1=CC=CC=C1 QBGQIMOGHUXVKB-UHFFFAOYSA-N 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• 125000004326 2H-pyran-2-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])(*)O1 0.000 description 1
• REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
• JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
• 125000006071 3,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
• 125000006072 3,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
• 125000006117 3,3-dimethylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000004336 3,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• GXORHMWHEXWRDU-UHFFFAOYSA-N 3,4-dihydrooxazol-5-yl Chemical group C1[N-]C[O+]=C1 GXORHMWHEXWRDU-UHFFFAOYSA-N 0.000 description 1
• CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
• FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000006041 3-hexenyl group Chemical group 0.000 description 1
• 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
• 125000006046 3-methyl-1-pentenyl group Chemical group 0.000 description 1
• 125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 1
• 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
• 125000006054 3-methyl-3-pentenyl group Chemical group 0.000 description 1
• 125000006057 3-methyl-4-pentenyl group Chemical group 0.000 description 1
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000006102 3-methylbutyl sulfinyl group Chemical group 0.000 description 1
• 125000006132 3-methylbutyl sulfonyl group Chemical group 0.000 description 1
• 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000005917 3-methylpentyl group Chemical group 0.000 description 1
• 125000006110 3-methylpentyl sulfinyl group Chemical group 0.000 description 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000001963 4 membered heterocyclic group Chemical group 0.000 description 1
• 125000004581 4,5-dihydroimidazol-1-yl group Chemical group N1(C=NCC1)* 0.000 description 1
• 125000004580 4,5-dihydroimidazol-2-yl group Chemical group N1C(=NCC1)* 0.000 description 1
• CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
• BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 description 1
• 125000006042 4-hexenyl group Chemical group 0.000 description 1
• 125000006047 4-methyl-1-pentenyl group Chemical group 0.000 description 1
• 125000006051 4-methyl-2-pentenyl group Chemical group 0.000 description 1
• 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
• 125000006111 4-methylpentyl sulfinyl group Chemical group 0.000 description 1
• 125000006141 4-methylpentyl sulfonyl group Chemical group 0.000 description 1
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
• ZGRZRTPZTSFZCT-UHFFFAOYSA-N 5-[5-[(2,6-difluorophenyl)methoxymethyl]-5-methyl-4h-1,2-oxazol-3-yl]-3-propyl-1,2-oxazole Chemical compound O1N=C(CCC)C=C1C(C1)=NOC1(C)COCC1=C(F)C=CC=C1F ZGRZRTPZTSFZCT-UHFFFAOYSA-N 0.000 description 1
• 125000006043 5-hexenyl group Chemical group 0.000 description 1
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 241000219144 Abutilon Species 0.000 description 1
• 235000005255 Allium cepa Nutrition 0.000 description 1
• 244000291564 Allium cepa Species 0.000 description 1
• 239000004254 Ammonium phosphate Substances 0.000 description 1
• 235000011446 Amygdalus persica Nutrition 0.000 description 1
• 244000099147 Ananas comosus Species 0.000 description 1
• 235000007119 Ananas comosus Nutrition 0.000 description 1
• 235000003911 Arachis Nutrition 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 244000003416 Asparagus officinalis Species 0.000 description 1
• 235000005340 Asparagus officinalis Nutrition 0.000 description 1
• 235000007320 Avena fatua Nutrition 0.000 description 1
• 241000209764 Avena fatua Species 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 244000060924 Brassica campestris Species 0.000 description 1
• 235000005637 Brassica campestris Nutrition 0.000 description 1
• 244000178924 Brassica napobrassica Species 0.000 description 1
• 235000011297 Brassica napobrassica Nutrition 0.000 description 1
• 235000006008 Brassica napus var napus Nutrition 0.000 description 1
• 240000000385 Brassica napus var. napus Species 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 1
• SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical group CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 244000052707 Camellia sinensis Species 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 241001049165 Caria Species 0.000 description 1
• 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
• 244000020518 Carthamus tinctorius Species 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• 235000005979 Citrus limon Nutrition 0.000 description 1
• 244000131522 Citrus pyriformis Species 0.000 description 1
• 235000009088 Citrus pyriformis Nutrition 0.000 description 1
• 235000005976 Citrus sinensis Nutrition 0.000 description 1
• 240000002319 Citrus sinensis Species 0.000 description 1
• 241000723377 Coffea Species 0.000 description 1
• 235000007460 Coffea arabica Nutrition 0.000 description 1
• 240000007154 Coffea arabica Species 0.000 description 1
• 241000228031 Coffea liberica Species 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229920000742 Cotton Polymers 0.000 description 1
• 235000009849 Cucumis sativus Nutrition 0.000 description 1
• 240000008067 Cucumis sativus Species 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
• 244000000626 Daucus carota Species 0.000 description 1
• 235000002767 Daucus carota Nutrition 0.000 description 1
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
• 240000003133 Elaeis guineensis Species 0.000 description 1
• 235000001950 Elaeis guineensis Nutrition 0.000 description 1
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 235000016623 Fragaria vesca Nutrition 0.000 description 1
• 244000307700 Fragaria vesca Species 0.000 description 1
• 241000233866 Fungi Species 0.000 description 1
• 244000299507 Gossypium hirsutum Species 0.000 description 1
• 235000003222 Helianthus annuus Nutrition 0.000 description 1
• 244000020551 Helianthus annuus Species 0.000 description 1
• 244000043261 Hevea brasiliensis Species 0.000 description 1
• 235000007340 Hordeum vulgare Nutrition 0.000 description 1
• 240000005979 Hordeum vulgare Species 0.000 description 1
• 235000008694 Humulus lupulus Nutrition 0.000 description 1
• 244000025221 Humulus lupulus Species 0.000 description 1
• 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 1
• 244000017020 Ipomoea batatas Species 0.000 description 1
• 235000002678 Ipomoea batatas Nutrition 0.000 description 1
• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
• 235000009496 Juglans regia Nutrition 0.000 description 1
• 240000007049 Juglans regia Species 0.000 description 1
• 239000005909 Kieselgur Substances 0.000 description 1
• 240000004322 Lens culinaris Species 0.000 description 1
• 235000010666 Lens esculenta Nutrition 0.000 description 1
• 235000019738 Limestone Nutrition 0.000 description 1
• 235000004431 Linum usitatissimum Nutrition 0.000 description 1
• 240000006240 Linum usitatissimum Species 0.000 description 1
• 244000100545 Lolium multiflorum Species 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 241000220225 Malus Species 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000004456 Manihot esculenta Nutrition 0.000 description 1
• 235000010624 Medicago sativa Nutrition 0.000 description 1
• 240000004658 Medicago sativa Species 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 241000234295 Musa Species 0.000 description 1
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
• 241000208134 Nicotiana rustica Species 0.000 description 1
• 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
• 244000061176 Nicotiana tabacum Species 0.000 description 1
• IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
• JZTPOMIFAFKKSK-UHFFFAOYSA-N O-phosphonohydroxylamine Chemical compound NOP(O)(O)=O JZTPOMIFAFKKSK-UHFFFAOYSA-N 0.000 description 1
• 235000002725 Olea europaea Nutrition 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 240000007594 Oryza sativa Species 0.000 description 1
• 235000007164 Oryza sativa Nutrition 0.000 description 1
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
• 244000193463 Picea excelsa Species 0.000 description 1
• 235000008124 Picea excelsa Nutrition 0.000 description 1
• 235000005205 Pinus Nutrition 0.000 description 1
• 241000218602 Pinus <genus> Species 0.000 description 1
• 235000010582 Pisum sativum Nutrition 0.000 description 1
• 240000004713 Pisum sativum Species 0.000 description 1
• 241000209504 Poaceae Species 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 239000004721 Polyphenylene oxide Substances 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 244000007021 Prunus avium Species 0.000 description 1
• 235000010401 Prunus avium Nutrition 0.000 description 1
• 240000005809 Prunus persica Species 0.000 description 1
• 235000014443 Pyrus communis Nutrition 0.000 description 1
• 240000001987 Pyrus communis Species 0.000 description 1
• 241001506137 Rapa Species 0.000 description 1
• 235000011483 Ribes Nutrition 0.000 description 1
• 241000220483 Ribes Species 0.000 description 1
• 240000000528 Ricinus communis Species 0.000 description 1
• 235000004443 Ricinus communis Nutrition 0.000 description 1
• 235000007201 Saccharum officinarum Nutrition 0.000 description 1
• 240000000111 Saccharum officinarum Species 0.000 description 1
• 235000007238 Secale cereale Nutrition 0.000 description 1
• 244000082988 Secale cereale Species 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000007230 Sorghum bicolor Nutrition 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• 235000006468 Thea sinensis Nutrition 0.000 description 1
• 244000299461 Theobroma cacao Species 0.000 description 1
• 235000009470 Theobroma cacao Nutrition 0.000 description 1
• 206010044278 Trace element deficiency Diseases 0.000 description 1
• 235000015724 Trifolium pratense Nutrition 0.000 description 1
• 240000002913 Trifolium pratense Species 0.000 description 1
• 235000021307 Triticum Nutrition 0.000 description 1
• 235000007264 Triticum durum Nutrition 0.000 description 1
• 241000209143 Triticum turgidum subsp. durum Species 0.000 description 1
• 235000010749 Vicia faba Nutrition 0.000 description 1
• 240000006677 Vicia faba Species 0.000 description 1
• 235000014787 Vitis vinifera Nutrition 0.000 description 1
• 240000006365 Vitis vinifera Species 0.000 description 1
• 241000607479 Yersinia pestis Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• GPUBQFLWXMSJJA-UHFFFAOYSA-N [3-(2-chloropyridin-3-yl)-5-methyl-4h-1,2-oxazol-5-yl]methanol Chemical compound O1C(C)(CO)CC(C=2C(=NC=CC=2)Cl)=N1 GPUBQFLWXMSJJA-UHFFFAOYSA-N 0.000 description 1
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 230000002411 adverse Effects 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910001413 alkali metal ion Inorganic materials 0.000 description 1
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
• 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
• 125000005037 alkyl phenyl group Chemical group 0.000 description 1
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
• 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
• 235000019289 ammonium phosphates Nutrition 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
• 235000011130 ammonium sulphate Nutrition 0.000 description 1
• 230000003698 anagen phase Effects 0.000 description 1
• HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
• 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
• 150000003931 anilides Chemical class 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 239000000010 aprotic solvent Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
• XUMDNHCCUNPEEY-UHFFFAOYSA-N bis(2-hydroxyethylidene)azanium Chemical compound OCC=[N+]=CCO XUMDNHCCUNPEEY-UHFFFAOYSA-N 0.000 description 1
• 238000009395 breeding Methods 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 235000014633 carbohydrates Nutrition 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
• 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 238000011097 chromatography purification Methods 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 239000003245 coal Substances 0.000 description 1
• 239000007931 coated granule Substances 0.000 description 1
• UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 125000004966 cyanoalkyl group Chemical group 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
• MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
• 150000004891 diazines Chemical class 0.000 description 1
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
• 239000002283 diesel fuel Substances 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 230000029087 digestion Effects 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
• LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
• 239000010459 dolomite Substances 0.000 description 1
• 229910000514 dolomite Inorganic materials 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 238000010410 dusting Methods 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 229940052303 ethers for general anesthesia Drugs 0.000 description 1
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 239000003337 fertilizer Substances 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 235000004426 flaxseed Nutrition 0.000 description 1
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 238000010353 genetic engineering Methods 0.000 description 1
• 235000002532 grape seed extract Nutrition 0.000 description 1
• 239000003630 growth substance Substances 0.000 description 1
• 125000004438 haloalkoxy group Chemical group 0.000 description 1
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
• 125000004995 haloalkylthio group Chemical group 0.000 description 1
• 150000003977 halocarboxylic acids Chemical class 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 230000026030 halogenation Effects 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 238000003306 harvesting Methods 0.000 description 1
• 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 150000004761 hexafluorosilicates Chemical class 0.000 description 1
• 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 1
• 239000003864 humus Substances 0.000 description 1
• YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 150000002430 hydrocarbons Chemical group 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 150000004679 hydroxides Chemical class 0.000 description 1
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
• 150000002460 imidazoles Chemical class 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000003350 kerosene Substances 0.000 description 1
• 238000004898 kneading Methods 0.000 description 1
• 239000006028 limestone Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
• XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
• 229910052808 lithium carbonate Inorganic materials 0.000 description 1
• 229910000103 lithium hydride Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000000395 magnesium oxide Substances 0.000 description 1
• CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
• WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• WNPVAXLJVUXYFU-UHFFFAOYSA-N n-cyclohex-2-en-1-ylidenehydroxylamine Chemical compound ON=C1CCCC=C1 WNPVAXLJVUXYFU-UHFFFAOYSA-N 0.000 description 1
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
• 239000012875 nonionic emulsifier Substances 0.000 description 1
• 231100001184 nonphytotoxic Toxicity 0.000 description 1
• SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
• 230000001473 noxious effect Effects 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 235000015097 nutrients Nutrition 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000004533 oil dispersion Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000004866 oxadiazoles Chemical class 0.000 description 1
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 238000005191 phase separation Methods 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 229960003424 phenylacetic acid Drugs 0.000 description 1
• 239000003279 phenylacetic acid Substances 0.000 description 1
• 150000008048 phenylpyrazoles Chemical class 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 230000003032 phytopathogenic effect Effects 0.000 description 1
• PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 239000002798 polar solvent Substances 0.000 description 1
• 229920000570 polyether Polymers 0.000 description 1
• 239000004848 polyfunctional curative Substances 0.000 description 1
• 229920001451 polypropylene glycol Polymers 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
• 229910000105 potassium hydride Inorganic materials 0.000 description 1
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000002203 pretreatment Methods 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
• 150000003217 pyrazoles Chemical class 0.000 description 1
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
• 150000004892 pyridazines Chemical class 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
• LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 235000013526 red clover Nutrition 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 210000000614 rib Anatomy 0.000 description 1
• 235000009566 rice Nutrition 0.000 description 1
• 239000012266 salt solution Substances 0.000 description 1
• 239000004576 sand Substances 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
• 239000004071 soot Substances 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
• 125000005537 sulfoxonium group Chemical group 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 229920002994 synthetic fiber Polymers 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
• HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
• 229910052723 transition metal Inorganic materials 0.000 description 1
• 150000003624 transition metals Chemical class 0.000 description 1
• 150000003918 triazines Chemical class 0.000 description 1
• GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
• 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• 238000009736 wetting Methods 0.000 description 1
• 239000002023 wood Substances 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1