BG64389B1 - 4-(3-хетероциклил-1-бензоил) пиразоли и използването им като хербициди - Google Patents

Info

Publication number

BG64389B1

BG64389B1 BG103663A BG10366399A BG64389B1 BG 64389 B1 BG64389 B1 BG 64389B1 BG 103663 A BG103663 A BG 103663A BG 10366399 A BG10366399 A BG 10366399A BG 64389 B1 BG64389 B1 BG 64389B1

Authority

BG

Bulgaria

Prior art keywords

alkyl

compounds

alkoxy

methyl

formula

Prior art date

1997-01-17

Links

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• 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 26
• 239000004009 herbicide Substances 0.000 title claims abstract description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 1922
• -1 C1-C6-halogenalkoxy Chemical group 0.000 claims abstract description 1865
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 99
• 125000001424 substituent group Chemical group 0.000 claims abstract description 62
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 60
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
• 239000001257 hydrogen Substances 0.000 claims abstract description 53
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 52
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 49
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 47
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 46
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 43
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 27
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
• 239000001301 oxygen Substances 0.000 claims abstract description 27
• 150000002367 halogens Chemical class 0.000 claims abstract description 25
• 238000000034 method Methods 0.000 claims abstract description 24
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 20
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 19
• 150000003839 salts Chemical class 0.000 claims abstract description 16
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 15
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims abstract description 10
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 7
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 7
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 4
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 38
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 239000011593 sulfur Substances 0.000 claims description 19
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 12
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 12
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 11
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 7
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 150000007942 carboxylates Chemical class 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 230000000269 nucleophilic effect Effects 0.000 claims description 3
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
• 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 2
• 230000008569 process Effects 0.000 claims description 2
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 9
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
• 239000002671 adjuvant Substances 0.000 claims 2
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 1
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 1
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 1
• 238000006073 displacement reaction Methods 0.000 claims 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 4
• 239000005864 Sulphur Substances 0.000 abstract 1
• 238000009313 farming Methods 0.000 abstract 1
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 abstract 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 383
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 319
• 239000000460 chlorine Substances 0.000 description 227
• 229910052801 chlorine Inorganic materials 0.000 description 186
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 182
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 57
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
• 239000000203 mixture Substances 0.000 description 52
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 46
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 45
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• 239000000243 solution Substances 0.000 description 40
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 38
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 36
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 36
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 35
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 34
• 239000002904 solvent Substances 0.000 description 33
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
• 239000002585 base Substances 0.000 description 26
• 239000012074 organic phase Substances 0.000 description 26
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 238000010992 reflux Methods 0.000 description 23
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• 238000003756 stirring Methods 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• 229910052794 bromium Inorganic materials 0.000 description 21
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 20
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 18
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 16
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 15
• 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 15
• 239000008346 aqueous phase Substances 0.000 description 14
• 238000005160 1H NMR spectroscopy Methods 0.000 description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• 150000002148 esters Chemical class 0.000 description 13
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 11
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 239000003480 eluent Substances 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• 239000011737 fluorine Substances 0.000 description 10
• 229910052731 fluorine Inorganic materials 0.000 description 10
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 10
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 10
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 10
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
• 239000007858 starting material Substances 0.000 description 10
• FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 9
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
• 150000001299 aldehydes Chemical class 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 238000001704 evaporation Methods 0.000 description 9
• 230000008020 evaporation Effects 0.000 description 9
• 125000001153 fluoro group Chemical group F* 0.000 description 9
• 150000002825 nitriles Chemical class 0.000 description 9
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 7
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 7
• 241000219146 Gossypium Species 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 7
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 235000009438 Gossypium Nutrition 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 125000005843 halogen group Chemical group 0.000 description 6
• 230000002363 herbicidal effect Effects 0.000 description 6
• 229940095102 methyl benzoate Drugs 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• JMARSTSWTFXHMC-UHFFFAOYSA-N 2-methyl-1h-pyrazol-3-one Chemical compound CN1NC=CC1=O JMARSTSWTFXHMC-UHFFFAOYSA-N 0.000 description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
• 239000005711 Benzoic acid Substances 0.000 description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 239000000470 constituent Substances 0.000 description 5
• 238000010438 heat treatment Methods 0.000 description 5
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 5
• 229910052763 palladium Inorganic materials 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 4
• 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 4
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 4
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 4
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 4
• KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• 241000196324 Embryophyta Species 0.000 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 125000003282 alkyl amino group Chemical group 0.000 description 4
• 235000010233 benzoic acid Nutrition 0.000 description 4
• 125000005997 bromomethyl group Chemical group 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 125000001188 haloalkyl group Chemical group 0.000 description 4
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 4
• 150000002576 ketones Chemical class 0.000 description 4
• 150000002923 oximes Chemical class 0.000 description 4
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 4
• 229910052723 transition metal Inorganic materials 0.000 description 4
• 150000003624 transition metals Chemical class 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• ZSHNSXSONOHWNB-UHFFFAOYSA-N 1-(2-chloro-3-methyl-4-methylsulfanylphenyl)ethanone Chemical compound CSC1=CC=C(C(C)=O)C(Cl)=C1C ZSHNSXSONOHWNB-UHFFFAOYSA-N 0.000 description 3
• 125000004743 1-methylethoxycarbonyl group Chemical group CC(C)OC(=O)* 0.000 description 3
• JURLTYXSZFLINT-UHFFFAOYSA-N 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=C(C(Cl)=O)C(Cl)=C1C1=NOCC1 JURLTYXSZFLINT-UHFFFAOYSA-N 0.000 description 3
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• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
• 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
• 239000008158 vegetable oil Substances 0.000 description 1
• 235000013311 vegetables Nutrition 0.000 description 1
• 238000010792 warming Methods 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1