NZ583033A - Tricyclic bridged cyclopentanedione derivatives as herbicides - Google Patents

Info

Publication number

NZ583033A

NZ583033A NZ583033A NZ58303308A NZ583033A NZ 583033 A NZ583033 A NZ 583033A NZ 583033 A NZ583033 A NZ 583033A NZ 58303308 A NZ58303308 A NZ 58303308A NZ 583033 A NZ583033 A NZ 583033A

Authority

NZ

New Zealand

Prior art keywords

formula

halogen

compound

optionally substituted

cyano

Prior art date

2007-08-08

Links

• Espacenet
• Global Dossier
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• 239000004009 herbicide Substances 0.000 title claims description 16
• CIISBNCSMVCNIP-UHFFFAOYSA-N cyclopentane-1,2-dione Chemical class O=C1CCCC1=O CIISBNCSMVCNIP-UHFFFAOYSA-N 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 807
• 241000196324 Embryophyta Species 0.000 claims abstract description 17
• 241000209504 Poaceae Species 0.000 claims abstract description 3
• -1 phenylaminocarbonyl Chemical group 0.000 claims description 1074
• 229910052739 hydrogen Inorganic materials 0.000 claims description 233
• 239000001257 hydrogen Substances 0.000 claims description 230
• 229910052736 halogen Inorganic materials 0.000 claims description 170
• 150000002367 halogens Chemical group 0.000 claims description 170
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 153
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 135
• 239000000203 mixture Substances 0.000 claims description 119
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 108
• 125000001072 heteroaryl group Chemical group 0.000 claims description 105
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 96
• 125000000217 alkyl group Chemical group 0.000 claims description 89
• 238000000034 method Methods 0.000 claims description 87
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 81
• 150000002431 hydrogen Chemical class 0.000 claims description 70
• 125000001424 substituent group Chemical group 0.000 claims description 63
• 239000002904 solvent Substances 0.000 claims description 62
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 238000002360 preparation method Methods 0.000 claims description 52
• 125000000623 heterocyclic group Chemical group 0.000 claims description 47
• 229920002554 vinyl polymer Chemical group 0.000 claims description 42
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 37
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 36
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 36
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 229910052760 oxygen Inorganic materials 0.000 claims description 30
• 239000000460 chlorine Substances 0.000 claims description 26
• 229910052717 sulfur Inorganic materials 0.000 claims description 26
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
• 239000003054 catalyst Substances 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
• 238000009472 formulation Methods 0.000 claims description 20
• 239000001301 oxygen Substances 0.000 claims description 20
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 230000002363 herbicidal effect Effects 0.000 claims description 15
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 239000011593 sulfur Substances 0.000 claims description 14
• 239000002671 adjuvant Substances 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 12
• 125000005240 diheteroarylamino group Chemical group 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 240000008042 Zea mays Species 0.000 claims description 9
• 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 8
• 125000005103 alkyl silyl group Chemical group 0.000 claims description 8
• 235000009973 maize Nutrition 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 150000001340 alkali metals Chemical class 0.000 claims description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 229910052783 alkali metal Inorganic materials 0.000 claims description 5
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
• 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
• KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 5
• COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 5
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
• PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 4
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
• 235000021307 Triticum Nutrition 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
• 125000004969 haloethyl group Chemical group 0.000 claims description 4
• 125000004970 halomethyl group Chemical group 0.000 claims description 4
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 4
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 3
• UKSLKNUCVPZQCQ-UHFFFAOYSA-N Fluxofenim Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)=NOCC1OCCO1 UKSLKNUCVPZQCQ-UHFFFAOYSA-N 0.000 claims description 3
• 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Chemical group 0.000 claims description 3
• 125000005107 alkyl diaryl silyl group Chemical group 0.000 claims description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 3
• 125000005110 aryl thio group Chemical group 0.000 claims description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims description 3
• OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 3
• 229910052701 rubidium Inorganic materials 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
• 125000005106 triarylsilyl group Chemical group 0.000 claims description 3
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
• 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims description 2
• YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 2
• 240000005979 Hordeum vulgare Species 0.000 claims description 2
• 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
• 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 2
• ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 229940126062 Compound A Drugs 0.000 claims 3
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 3
• 241000209140 Triticum Species 0.000 claims 3
• 102220598877 DNA-directed RNA polymerases I, II, and III subunit RPABC4_R15A_mutation Human genes 0.000 claims 2
• 102220598964 DNA-directed RNA polymerases I, II, and III subunit RPABC4_R22A_mutation Human genes 0.000 claims 2
• 102220503972 Endogenous retrovirus group K member 6 Rec protein_R16A_mutation Human genes 0.000 claims 2
• 102220587413 N-acetylserotonin O-methyltransferase-like protein_R23A_mutation Human genes 0.000 claims 2
• 208000027418 Wounds and injury Diseases 0.000 claims 2
• 230000006378 damage Effects 0.000 claims 2
• 208000014674 injury Diseases 0.000 claims 2
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
• 102220473072 Chemerin-like receptor 2_R14Q_mutation Human genes 0.000 claims 1
• 102220473068 Chemerin-like receptor 2_R17Q_mutation Human genes 0.000 claims 1
• 102220503974 Endogenous retrovirus group K member 6 Rec protein_R13A_mutation Human genes 0.000 claims 1
• 102220503970 Endogenous retrovirus group K member 6 Rec protein_R18A_mutation Human genes 0.000 claims 1
• 102220595577 Major vault protein_R24A_mutation Human genes 0.000 claims 1
• ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical group CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims 1
• 230000001419 dependent effect Effects 0.000 claims 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 102220482205 tRNA pseudouridine synthase A_R21A_mutation Human genes 0.000 claims 1
• 244000045561 useful plants Species 0.000 claims 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 97
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
• 239000011651 chromium Substances 0.000 description 60
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 57
• 239000000243 solution Substances 0.000 description 50
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 46
• 239000002585 base Substances 0.000 description 40
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 39
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
• 239000011541 reaction mixture Substances 0.000 description 34
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 29
• 229910052794 bromium Inorganic materials 0.000 description 29
• 239000003921 oil Substances 0.000 description 29
• 235000019198 oils Nutrition 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
• 239000004480 active ingredient Substances 0.000 description 27
• 238000005160 1H NMR spectroscopy Methods 0.000 description 26
• 239000000706 filtrate Substances 0.000 description 26
• 239000000741 silica gel Substances 0.000 description 25
• 229910002027 silica gel Inorganic materials 0.000 description 25
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 125000001246 bromo group Chemical group Br* 0.000 description 24
• 229910052801 chlorine Inorganic materials 0.000 description 24
• 238000004440 column chromatography Methods 0.000 description 24
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 24
• 125000001309 chloro group Chemical group Cl* 0.000 description 23
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 20
• 229910052763 palladium Inorganic materials 0.000 description 20
• 239000000654 additive Substances 0.000 description 18
• NUOXSJGIRWCWNR-UHFFFAOYSA-N decane-3,5-dione Chemical compound CCCCCC(=O)CC(=O)CC NUOXSJGIRWCWNR-UHFFFAOYSA-N 0.000 description 16
• 239000007787 solid Substances 0.000 description 15
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
• 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 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 239000003153 chemical reaction reagent Substances 0.000 description 13
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 13
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 13
• 239000012267 brine Substances 0.000 description 12
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
• 230000009467 reduction Effects 0.000 description 12
• 238000006722 reduction reaction Methods 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 11
• 150000003839 salts Chemical class 0.000 description 11
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• 239000013543 active substance Substances 0.000 description 10
• 150000001336 alkenes Chemical class 0.000 description 10
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical group [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 9
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
• 239000005909 Kieselgur Substances 0.000 description 9
• 230000000996 additive effect Effects 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 239000000284 extract Substances 0.000 description 9
• 230000026030 halogenation Effects 0.000 description 9
• 238000005658 halogenation reaction Methods 0.000 description 9
• 150000002576 ketones Chemical class 0.000 description 9
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
• 239000004094 surface-active agent Substances 0.000 description 9
• PAEVMTYBHARJPO-CMDGGOBGSA-N (E)-dec-4-en-3-one Chemical compound CCCCC\C=C\C(=O)CC PAEVMTYBHARJPO-CMDGGOBGSA-N 0.000 description 8
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 8
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 8
• 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 8
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 8
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 8
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 8
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 8
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 8
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 8
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 8
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 8
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 8
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