TW202116737A - 除草化合物 - Google Patents
除草化合物 Download PDFInfo
- Publication number
- TW202116737A TW202116737A TW109124089A TW109124089A TW202116737A TW 202116737 A TW202116737 A TW 202116737A TW 109124089 A TW109124089 A TW 109124089A TW 109124089 A TW109124089 A TW 109124089A TW 202116737 A TW202116737 A TW 202116737A
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- alkoxy
- methyl
- group
- haloalkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 195
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 238000000034 method Methods 0.000 claims abstract description 21
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 182
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 239000004009 herbicide Substances 0.000 claims description 21
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 15
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 15
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 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 claims description 13
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 12
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 11
- 239000002671 adjuvant Substances 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002790 naphthalenes Chemical class 0.000 claims description 10
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 9
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000000575 pesticide Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 6
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims description 6
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 6
- DNNVRTZJRKIUFK-UHFFFAOYSA-N 3,4-dihydroquinoline Chemical compound C1=CC=C2N=CCCC2=C1 DNNVRTZJRKIUFK-UHFFFAOYSA-N 0.000 claims description 6
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 6
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 4
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 4
- 230000000361 pesticidal effect Effects 0.000 claims description 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 3
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 2
- 230000012010 growth Effects 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 36
- 238000002360 preparation method Methods 0.000 abstract description 10
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000008635 plant growth Effects 0.000 abstract description 2
- TVKFDBOFBKXOQT-UHFFFAOYSA-N 5-phenyl-1h-pyridazin-6-one Chemical class O=C1NN=CC=C1C1=CC=CC=C1 TVKFDBOFBKXOQT-UHFFFAOYSA-N 0.000 abstract 1
- GXZLRCBECYMKCZ-UHFFFAOYSA-N 5-phenylpyridazine-3,4-dione Chemical class C1(=CC=CC=C1)C=1C(C(N=NC=1)=O)=O GXZLRCBECYMKCZ-UHFFFAOYSA-N 0.000 abstract 1
- 244000045561 useful plants Species 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1017
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 70
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 62
- 238000005481 NMR spectroscopy Methods 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 51
- 239000002585 base Substances 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000000460 chlorine Substances 0.000 description 46
- 229910052801 chlorine Inorganic materials 0.000 description 42
- 239000002904 solvent Substances 0.000 description 40
- 150000002148 esters Chemical group 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 239000011737 fluorine Substances 0.000 description 33
- 229910052731 fluorine Inorganic materials 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 230000003197 catalytic effect Effects 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
- 229920002554 vinyl polymer Polymers 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 20
- 238000011065 in-situ storage Methods 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 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 14
- 235000017016 Setaria faberi Nutrition 0.000 description 13
- 241001355178 Setaria faberi Species 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 240000007218 Ipomoea hederacea Species 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000007921 spray Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 11
- 241000894007 species Species 0.000 description 11
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 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
- 229920001213 Polysorbate 20 Polymers 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000000468 ketone group Chemical group 0.000 description 8
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 8
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 240000006995 Abutilon theophrasti Species 0.000 description 7
- 244000058871 Echinochloa crus-galli Species 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 235000005822 corn Nutrition 0.000 description 7
- 244000038559 crop plants Species 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 239000012041 precatalyst Chemical group 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000004327 boric acid Substances 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 150000007857 hydrazones Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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Abstract
本發明關於具有式 (I) 之除草劑經取代的苯基-嗒𠯤-二酮和經取代的苯基-嗒𠯤酮衍生物,以及用於製備此類衍生物之方法和中間體。本發明進一步延伸到包含此類衍生物的除草組成物,以及此類化合物和組成物在有用植物的作物中控制不希望的植物生長之用途:特別地控制雜草如闊葉雙子葉雜草之用途。
Description
本發明關於具有式 (I) 之除草劑經取代的苯基-嗒𠯤-二酮和經取代的苯基-嗒𠯤酮衍生物,以及用於製備此類衍生物之方法和中間體。本發明進一步延伸到包含此類衍生物之除草組成物,以及此類化合物和組成物在有用植物的作物中控制不希望的植物生長之用途:特別地控制雜草如闊葉雙子葉雜草之用途。
除草劑嗒𠯤酮係從WO 2009/086041已知的。此外,除草劑5/6員雜環基取代的嗒𠯤酮係從WO 2011/045271已知的。同時WO 2013/160126描述了吲哚基-嗒𠯤酮衍生物,該等衍生物展示出除草活性。
本發明係基於以下發現:具有式 (I) 之經取代的苯基-嗒𠯤-二酮和經取代的苯基-嗒𠯤酮衍生物展示了出人意料地良好的除草活性。
因此,在第一方面,提供了一種具有式 (I) 之化合物(I),
或其鹽或N-氧化物,其中,
R1
選自由以下組成之群組:C1
-C4
烷基、C3
-C6
環烷基、C3
-C6
烷氧基、C1
-C2
烷氧基-C1
-C2
烷基-、C2
-C4
烯基、C1
-C4
鹵代烷基、氰基-C1
-C4
烷基、C2
-C4
鹵代烯基、C2
-C4
炔基和C2
-C4
鹵代炔基;
R2
選自由以下組成之群組:氫、鹵素、氰基、C1
-C6
烷基、C1
-C6
鹵代烷基、C1
-C6
鹵代烷氧基、C1
-C3
鹵代烷氧基-C1
-C3
烷基-、C1
-C6
烷氧基、C1
-C3
烷氧基-C1
-C3
烷基、C1
-C3
烷氧基-C1
-C3
烷氧基-C1
-C3
烷基-、C3
-C6
環烷基、C2
-C6
烯基、C2
-C6
鹵代烯基、C2
-C6
炔基、C1
-C6
羥基烷基-、C1
-C6
烷基羰基-、-S(O)m
C1
-C6
烷基、胺基、C1
-C6
烷基胺基、C1
-C6
二烷基胺基、-C(C1
-C3
烷基)=N-O-C1
-C3
烷基和C2
-C6
鹵代炔基;
G係氫、或C(O)R3
;
R3
選自由以下組成之群組:C1
-C6
烷基、C2
-C6
烯基、C2
-C6
炔基、C1
-C6
烷基-S-、C1
-C6
烷氧基、-NR4
R5
和視需要被一個或多個R6
取代的苯基;
R4
和R5
各自獨立地選自由以下組成之群組:氫、C1
-C6
烷基、C1
-C6
烷氧基和C3
-C6
環烷基,或者R4
和R5
一起可以形成𠰌啉基環;並且,
R6
選自由以下組成之群組:鹵素、氰基、硝基、C1
-C3
烷基、C1
-C3
鹵代烷基、C1
-C3
烷氧基以及C1
-C3
鹵代烷氧基;
X和Y各自獨立地是氫、C1
-C3
烷基、環丙基、C1
-C3
烷氧基、C1
-C3
鹵代烷基、C1
-C3
鹵代烷氧基、或鹵素;
D係經取代或未經取代的萘環系統,或包含1、2、3或4個獨立地選自氧、氮和硫的雜原子的經取代或未經取代的8-10員二環飽和、部分飽和或不飽和的雜環系統,並且其中當D被取代時,其在至少一個環碳原子上被R8
取代和/或在至少一個環氮原子上被R9
取代;
每個R8
獨立地是氧、羥基、鹵素、氰基、C1
-C6
烷基、C1
-C6
鹵代烷基、C3
-C6
-環烷基、C1
-C6
烷氧基、C1
-C6
鹵代烷氧基、C1
-C3
烷氧基-C1
-C3
烷基、C1
-C3
鹵代烷氧基-C1
-C3
烷基-、C1
-C3
烷氧基-C1
-C3
烷氧基-C1
-C3
烷基-、C2
-C6
烯基、C2
-C6
鹵代烯基、C2
-C6
炔基、C2
-C6
鹵代炔基、C1
-C6
羥基烷基-、C1
-C6
烷基羰基-、C1
-C6
鹵代烷基羰基-、C3
-C6
環烷基羰基-、C1
-C6
烷基-S(O)m
-、-S(O)m
-C1
-C6
鹵代烷基、-S(O)m
-C3
-C6
環烷基、-O-S(O)2
C1
-C3
烷基、-C1
-C3
烷基-S(O)m
-C1
-C6
烷基、-C1
-C3
烷基-S(O)m
-C1
-C6
鹵代烷基、-C1
-C3
烷基-S(O)m
-C3
-C6
環烷基、氰基-C1
-C6
-烷基-、-NR4
R5
、-C(C1
-C3
烷基)=N-O-C1
-C3
烷基、-C(S)NH2
、C1
-C6
烷基胺基硫代羰基-、二(C1
-C6
烷基)胺基硫代羰基-、C3
-C6
-環烷基胺基-硫代羰基-S(O)2
NH2
、-S(O)2
NHC(O)C1
-C3
烷基、C1
-C6
烷基胺基磺醯基-、二(C1
-C6
烷基)胺基磺醯基-、C3
-C6
-環烷基胺基-磺醯基-、-C(O)OH、-C(O)OC1
-C6
烷基、-C(O)NHS-(O)2
C1
-C6
烷基、-C(O)NR4
R5
、-NR4
C(O)NR4
R5
、C1
-C6
烷基羰基(C1
-C6
烷基)胺基-、C1
-C6
鹵代烷基羰基胺基-、C1
-C6
鹵代烷基羰基(C1
-C6
烷基)胺基-、C1
-C6
烷氧基羰基胺基-、C1
-C6
烷氧基羰基(C1
-C6
烷基)胺基-、C1
-C6
烷基磺醯基胺基-、C1
-C6
烷基磺醯基(C1
-C6
烷基)胺基-、C1
-C6
鹵代烷基磺醯基胺基-、C1
-C6
鹵代烷基磺醯基(C1
-C6
烷基)胺基-、C3
-C6
環烷基磺醯基胺基-、C3
-C6
環烷基磺醯基(C1
-C6
烷基)胺基-、C1
-C6
烷基胺基羰基胺基-、C1
-C6
烷基胺基羰基(C1
-C6
烷基)胺基、二(C1
-C6
烷基)胺基羰基胺基-、C1
-C6
鹵代烷基胺基羰基胺基-、C1
-C6
鹵代烷基胺基羰基(C1
-C6
烷基)胺基、二(C1
-C6
鹵代烷基)胺基羰基胺基-、二(C1
-C6
鹵代烷基)胺基羰基(C1
-C6
烷基)胺基-、羥基胺基-、羥基(C1
-C6
烷基)胺基、C1
-C6
烷氧基胺基、C1
-C6
烷氧基(C1
-C6
烷基)胺基、C1
-C6
鹵代烷氧基胺基、C1
-C6
鹵代烷氧基(C1
-C6
烷基)胺基、或選自由苯基環、5-6員雜芳基環和3-6員雜環基環組成的組的環系統,其中所述環系統被0至5個R16
取代;
m係0、1或2的整數;
每個R9
獨立地是C1
-C6
烷基、C1
-C6
鹵代烷基、羥基、C1
-C4
烷氧基、C1
-C4
烷硫基、C3
-C6
-環烷基、C1
-C3
烷氧基-C1
-C3
烷基、C1
-C3
鹵代烷氧基-C1
-C3
烷基-、C1
-C3
烷氧基-C1
-C3
烷氧基-C1
-C3
烷基-、C1
-C6
羥基烷基-、-C1
-C3
烷基-S(O)m
-C1
-C6
烷基、-C1
-C3
烷基-S(O)m
-C1
-C6
鹵代烷基、-C1
-C3
烷基-S(O)m
-C3
-C6
環烷基、氰基-C1
-C6
-烷基-、或選自由苯基環、5-6員雜芳基環和3-6員雜環基環組成之群組的環系統,其中所述環系統被0至5個R16
取代;
每個R16
獨立地是鹵素、氰基、C1
-C6
烷基、C1
-C6
鹵代烷基、C1
-C6
烷氧基或C1
-C6
鹵代烷氧基;並且,
W係W1或W2、或W3,
其中
「a」表示與苯基-嗒𠯤酮/苯基-嗒𠯤二酮部分的附接點,
「b」表示與環D的附接點,
R10
、R12
、R14
和R15
各自獨立地是氫、C1
-C3
烷基或C1
-C3
鹵代烷基;或者R10
和R12
與它們所連接的碳原子一起形成C3
-C6
碳環;並且
R11
和R13
各自獨立地是氫、鹵素、C1
-C3
烷基、或C1
-C3
鹵代烷基,其前提係當R11
或R13
之一係鹵素、C1
-C3
烷基或C1
-C3
鹵代烷基時,另一個係氫。
具有式 (I) 之化合物可以含有不對稱中心並且可以作為單一鏡像異構物、以任何比例的鏡像異構物對而存在,或其中存在多於一個不對稱中心,含有所有可能比率的非鏡像異構物。典型地,與其他可能性相比,該鏡像異構物之一具有增強的生物活性。
類似地,在存在雙取代烯烴的情況下,該等可以以E或Z形式或作為任何比例的二者的混合物而存在。
應當理解的是,所有互變異構形式(單一互變異構物或其混合物)、外消旋混合物和單一異構物被包括在本發明之範圍內。
每個烷基部分單獨或者作為較大基團(如烷氧基、烷硫基、烷氧基羰基、烷基羰基、烷基胺基羰基或二烷基胺基羰基等)的一部分可為直鏈或支鏈的。典型地,該烷基係例如甲基、乙基、正丙基、異丙基、正丁基、二級丁基、異丁基、三級丁基、正戊基、新戊基、或正己基。烷基通常是C1
-C6
烷基(除了在已經更狹窄地定義時),但較佳的是C1
-C4
烷基或C1
-C3
烷基,並且更較佳的是C1
-C2
烷基(如甲基)。
烯基與炔基部分可以處於直鏈或支鏈的形式,並且該等烯基部分適當時可為具有 (E
)-或 (Z
)-組態。烯基或炔基部分典型地是C2
-C4
烯基或C2
-C4
炔基,更確切地說係乙烯基、烯丙基、乙炔基、炔丙基或丙-1-炔基。烯基與炔基部分能以任何組合包含一個或多個雙和/或三鍵;但是較佳的是僅包含一個雙鍵(對於烯基)或僅包含一個三鍵(對於炔基)。
較佳的是,術語環烷基係指環丙基、環丁基、環戊基或環己基。
在本說明書的背景下,術語「芳基」較佳的是意指苯基。如本文使用的,術語「雜芳基」意指包含至少一個環雜原子的單環或二環的芳香族環系統。較佳的是,單環環系統將包含1、2或3個環雜原子,並且二環環系統將包含1、2、3或4個環雜原子,每個雜原子獨立地選自氮、氧和硫。
典型地,單環雜芳基環選自由以下組成之群組:呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、㗁唑基、異㗁唑基、噻唑基、異噻唑基、1,2,4-㗁二唑基、1,3,4-㗁二唑基、1,2,5-㗁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、嗒𠯤基、吡𠯤基、1,2,3-三𠯤基、1,2,4-三𠯤基、或1,3,5-三𠯤基環。
典型地,二環雜芳基環系統選自由以下組成之群組:吲口巾、吲哚、異吲哚、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、嘌呤、4H-喹口巾、喹啉、異喹啉、口辛啉、酞𠯤、喹㗁啉、1-8-口奈啶、或喋啶環系統。
雜環基以及雜環(單獨的或作為更大基團(如雜環基-烷基-)的一部分)係包含至少一個雜原子的環系統並且可為處於單環或雙環形式,並且可為部分飽和或完全飽和的。較佳的是,雜環基將包含最多達兩個雜原子,該等雜原子將較佳的是選自氮、氧以及硫。雜環基團的實例包括氧雜環丁烷基、硫雜環丁烷基、氮雜環丁烷基以及7-氧雜-雙環[2.2.1]庚-2-基。包含單個氧原子作為雜原子的雜環基係最較佳的。
鹵素(或鹵代)涵蓋了氟、氯、溴或碘。該鹵素對應地應用於其他定義背景下的鹵素,如鹵代烷基或鹵代苯基。
具有從1至6個碳原子鏈長的鹵代烷基係,例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基和2,2,2-三氯乙基、七氟正丙基以及全氟正己基。
烷氧基較佳的是具有從1至6個碳原子的鏈長。烷氧基係,例如甲氧基、乙氧基、丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基或三級丁氧基或戊氧基或己氧基異構物,較佳的是甲氧基和乙氧基。還應當理解的是,兩個烷氧基取代基可以存在於相同碳原子上。
鹵代烷氧基係,例如氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、2-氟乙氧基、2-氯乙氧基、2,2-二氟乙氧基或2,2,2-三氯乙氧基,較佳的是二氟甲氧基、2-氯乙氧基或三氟甲氧基。
C1
-C6
烷基-S-(烷硫基)係,例如甲硫基、乙硫基、丙硫基、異丙硫基、正丁硫基、異丁硫基、二級丁硫基或三級丁硫基,較佳的是甲硫基或乙硫基。
C1
-C6
烷基-S(O)-(烷基亞磺醯基)係,例如,甲基亞磺醯基、乙基亞磺醯基、丙基亞磺醯基、異丙基亞磺醯基、正丁基亞磺醯基、異丁基亞磺醯基、二級丁基亞磺醯基或三級丁基亞磺醯基,較佳的是甲基亞磺醯基或乙基亞磺醯基。
C1
-C6
烷基-S(O)2
-(烷基磺醯基)係,例如,甲基磺醯基、乙基磺醯基、丙基磺醯基、異丙基磺醯基、正丁基磺醯基、異丁基磺醯基、二級丁基磺醯基或三級丁基磺醯基,較佳的是甲基磺醯基或乙基磺醯基。
本發明還包括農藝學上可接受的鹽,具有式 (I) 之化合物可以與胺(例如氨、二甲胺和三乙胺)、鹼金屬和鹼土金屬鹼或季銨鹽鹼形成該等鹽。在用作成鹽物的鹼金屬和鹼土金屬氫氧化物、氧化物、烷氧化物以及碳酸氫鹽和碳酸鹽之中,強調的是鋰、鈉、鉀、鎂和鈣的氫氧化物、烷氧化物、氧化物以及碳酸鹽,但尤其是鈉、鎂和鈣的那些。還可以使用對應的三甲基鋶鹽。根據本發明之具有式 (I) 之化合物還包括在鹽形成期間可以形成的水合物。
R1
、R2
、R3
、R4
、R5
、R6
、R8
、R9
、R10
、R11
、R12
、R13
、R14
、R15
、W、D、G、X、Y、Z和m的較佳的值係如以下列出的,並且根據本發明之具有式 (I) 之化合物可以包括所述值的任何組合。技術人員將理解,用於任何指定組的實施方式的值可以與用於任何其他組的實施方式的值組合,其中此類組合不相互排斥。
較佳的是,R1
選自由以下組成之群組:甲基、乙基、丙基(具體地是正丙基或環丙基)、炔丙基或C1
鹵代烷基。更較佳的是,R1
係甲基、乙基、環丙基、炔丙基或C1
氟烷基。還更較佳的是,R1
係甲基、乙基、環丙基或炔丙基。最較佳的是,R1
係甲基。
較佳的是,R2
選自由以下組成之群組:氫、鹵素、C1
-C6
烷基、C1
-C6
鹵代烷基、C1
-C6
烷氧基、C1
-C3
烷氧基-C1
-C3
烷基、C3
-C6
環烷基、C2
-C6
烯基、C2
-C6
鹵代烯基、C2
-C6
炔基和C2
-C6
鹵代炔基。更較佳的是,R2
選自由以下組成之群組:氯、氟、甲基、乙基、環丙基、三氟甲基和甲氧基甲基;還更較佳的是,氯、環丙基、三氟甲基或甲基;最較佳的是,氯或甲基。在本發明之一組實施方式中,R2
係氫。在另外一組實施方式中,R2
係環丙基;在第三組實施方式中,R2
係甲基,在第四組實施方式中,R2
係三氟甲基,並且在第五組實施方式中,R2
係氯。如本文所述,G可為氫或–C(O)-R3
,並且R3
選自由以下組成之群組:C1
-C6
烷基、C2
-C6
烯基、C2
-C6
炔基、C1
-C6
烷基-S-、C1
-C6
烷氧基、-NR4
R5
以及視需要被一個或多個R6
取代的苯基。如本文所定義的,R4
和R5
各自獨立地選自由以下組成之群組:氫、C1
-C6
烷基、C1
-C6
烷氧基-和C3
-C6
環烷基;或者它們可以一起形成𠰌啉基環。較佳的是,R4
和R5
各自獨立地選自由以下組成之群組:甲基、乙基、丙基、甲氧基、乙氧基和丙氧基。R6
選自由以下組成之群組:鹵素、氰基、硝基、C1
-C3
烷基、C1
-C3
鹵代烷基、C1
-C3
烷氧基以及C1
-C3
鹵代烷氧基。較佳的是,R6
選自由以下組成之群組:鹵素、甲基、乙基、三氟甲基、甲氧基和乙氧基。
較佳的是,R3
係C1
-C4
烷基、C2
-C3
烯基、C2
-C3
炔基、C1
-C4
烷氧基、或-NR4
R5
,其中R4
和R5
一起形成𠰌啉基環。更較佳的是,R3
係異丙基、三級丁基、甲基、乙基、炔丙基、甲氧基、乙氧基或三級丁氧基
在一組實施方式中,G係氫或-C(O)-R3
,其中R3
係C1
-C4
烷基、C2
-C3
烯基、C2
-C3
炔基或-C1
-C3
烷氧基。在另外一組實施方式中,G係氫或-C(O)-R3
,其中R3
係異丙基、三級丁基、甲基、乙基、炔丙基或甲氧基。然而,特別較佳的是,G係氫、或-C(O)-R3
,其中R3
係異丙基。
X較佳的是氫、鹵素、或C1
鹵代烷基,更較佳的是氫、氟、氯、溴、或C1
氟烷基並且還更較佳的是氫、氟、氯或三氟甲基。在一組實施方式中,較佳的是,相對於嗒𠯤酮/嗒𠯤二酮部分(基團Q),X係在鄰位(6位)。特別較佳的是,X係氟、氯或C1
-鹵代烷基(特別是C1
氟烷基)並且相對於嗒𠯤酮/嗒𠯤二酮部分(基團Q)係在鄰位(6位)。最較佳的是,X係氟並且相對於嗒𠯤酮/嗒𠯤-二酮部分係在鄰位(6位)。
Y較佳的是氫、C1
-C3
烷基、環丙基、C1
-C3
鹵代烷基、或鹵素。更較佳的是,Y係氫、氯、氟、或溴。
在一組實施方式中,較佳的是相對於-W-D部分,Y係在鄰位(3位)。在另外一組實施方式中,相對於嗒𠯤酮/嗒𠯤二酮部分(基團Q),Y係在對位。
特別較佳的是,相對於-W-D部分,Y係在鄰位(3位),並且是鹵素,特別是氯或氟;更較佳的是氯。
在一組特別較佳的實施方式中,X係氟並且相對於嗒𠯤酮/嗒𠯤-二酮部分係在鄰位(6位)並且Y係氯並且相對於-W-D部分係在鄰位(3位)。
如本文所述,D係經取代或未經取代的萘環系統,或包含1、2、3或4個獨立地選自氧、氮和硫的雜原子的經取代或未經取代的8-10員二環飽和、部分飽和或不飽和的雜環系統,並且其中當D被取代時,其在至少一個環碳原子上被R8
取代和/或在適當時在環氮原子上被R9
取代。在一組較佳的實施方式中,環系統D藉由環碳原子連接到分子的剩餘部分。
較佳的是,D係經取代或未經取代的萘環系統或係包含1、2、3或4個獨立地選自氧、氮和硫的雜原子的經取代或未經取代的8-10-員二環雜環。更較佳的是,D係經取代(被至少一個R8
和/或R9
,如本文所述)或未經取代的萘、吲口巾、吲哚、異吲哚、吲哚啉、異吲哚啉、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并㗁唑、苯并間二氧雜環戊烯(benzodioxole)、嘌呤、4H-喹口巾、喹啉、異喹啉、四氫喹啉、口辛啉、酞𠯤、喹㗁啉、1-8-口奈啶、喋啶、1H-吡咯并[2,3-b]吡啶、咪唑并[1,2-a]吡𠯤或1H-苯并三唑環系統。
甚至更較佳的是,D係經取代(被至少一個R8
和/或R9
,如本文所述)或未經取代的萘、吲口巾、吲哚、異吲哚、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并㗁唑、嘌呤、4H-喹口巾、喹啉、異喹啉、四氫喹啉、口辛啉、酞𠯤、喹㗁啉、1-8-口奈啶、或喋啶環系統。
更較佳的是,在此類實施方式中,D係經取代(如本文所述)或未經取代的萘、喹啉、四氫喹啉、吲哚、或苯并㗁唑環。
較佳的是,每個R8
獨立地是氧、羥基、鹵素、氰基、C1
-C6
烷基、C1
-C6
鹵代烷基、C3
-C6
-環烷基、C1
-C6
烷氧基、C1
-C6
鹵代烷氧基、C1
-C3
烷氧基-C1
-C3
烷基、C1
-C3
鹵代烷氧基-C1
-C3
烷基-、C1
-C3
烷氧基-C1
-C3
烷氧基-C1
-C3
烷基-、C2
-C6
烯基、C2
-C6
鹵代烯基、C2
-C6
炔基、C2
-C6
鹵代炔基、C1
-C6
羥基烷基-、C1
-C6
烷基羰基-、C1
-C6
鹵代烷基羰基-、C3
-C6
環烷基羰基-、C1
-C6
烷基-S(O)m
-、-S(O)m
-C1
-C6
鹵代烷基、-S(O)m
-C3
-C6
環烷基、-O-S(O)2
C1
-C3
烷基、-C1
-C3
烷基-S(O)m
-C1
-C6
烷基、-C1
-C3
烷基-S(O)m
-C1
-C6
鹵代烷基、-C1
-C3
烷基-S(O)m
-C3
-C6
環烷基、氰基-C1
-C6
-烷基-、-NR4
R5
、-C(C1
-C3
烷基)=N-O-C1
-C3
烷基、-C(S)NH2
、C1
-C6
烷基胺基硫代羰基-、二(C1
-C6
烷基)胺基硫代羰基-、C3
-C6
-環烷基胺基-硫代羰基-S(O)2
NH2
、-S(O)2
NHC(O)C1
-C3
烷基、C1
-C6
烷基胺基磺醯基-、二(C1
-C6
烷基)胺基磺醯基-、C3
-C6
-環烷基胺基-磺醯基-、-C(O)OH、-C(O)OC1
-C6
烷基、-C(O)NHS-(O)2
C1
-C6
烷基、-C(O)NR4
R5
、-NR4
C(O)NR4
R5
、C1
-C6
烷基羰基(C1
-C6
烷基)胺基-、C1
-C6
鹵代烷基羰基胺基-、C1
-C6
鹵代烷基羰基(C1
-C6
烷基)胺基-、C1
-C6
烷氧基羰基胺基-、C1
-C6
烷氧基羰基(C1
-C6
烷基)胺基-、C1
-C6
烷基磺醯基胺基-、C1
-C6
烷基磺醯基(C1
-C6
烷基)胺基-、C1
-C6
鹵代烷基磺醯基胺基-、C1
-C6
鹵代烷基磺醯基(C1
-C6
烷基)胺基-、C3
-C6
環烷基磺醯基胺基-、C3
-C6
環烷基磺醯基(C1
-C6
烷基)胺基-、C1
-C6
烷基胺基羰基胺基-、C1
-C6
烷基胺基羰基(C1
-C6
烷基)胺基、二(C1
-C6
烷基)胺基羰基胺基-、C1
-C6
鹵代烷基胺基羰基胺基-、C1
-C6
鹵代烷基胺基羰基(C1
-C6
烷基)胺基、二(C1
-C6
鹵代烷基)胺基羰基胺基-、二(C1
-C6
鹵代烷基)胺基羰基(C1
-C6
烷基)胺基-、羥基胺基-、羥基(C1
-C6
烷基)胺基、C1
-C6
烷氧基胺基、C1
-C6
烷氧基(C1
-C6
烷基)胺基、C1
-C6
鹵代烷氧基胺基、C1
-C6
鹵代烷氧基(C1
-C6
烷基)胺基。
更較佳的是,每個R8
獨立地是氧、羥基、鹵素、氰基、C1
-C6
烷基、C1
-C6
鹵代烷基、C1
-C6
鹵代烷氧基、C1
-C3
鹵代烷氧基-C1
-C3
烷基-、C1
-C6
烷氧基、C1
-C3
烷氧基-C1
-C3
烷基、C1
-C3
烷氧基-C1
-C3
烷氧基-C1
-C3
烷基-、C3
-C6
環烷基、C2
-C6
烯基、C2
-C6
鹵代烯基、C2
-C6
炔基、C1
-C6
羥基烷基-、C1
-C6
烷基羰基-、C1
-C6
烷基-S(O)m
-、胺基、C1
-C6
烷基胺基、C1
-C6
二烷基胺基、-C(C1
-C3
烷基)=N-O-C1
-C3
烷基或C2
-C6
鹵代炔基。
甚至更較佳的是,每個R8
獨立地是羥基、鹵素、C1
-C6
烷基、C1
-C6
鹵代烷基、C1
-C6
烷氧基。甚至還更較佳的是,每個R8
獨立地是C1
-C3
烷基、C1
-C3
鹵代烷基、氯、氟、羥基、或C1
-C3
烷氧基。
較佳的是,每個R9
獨立地是C1
-C4
烷基、C1
-C4
鹵代烷基、羥基、C1
-C4
烷氧基、或C1
-C4
烷硫基。更較佳的是,每個R9
獨立地是C1
-C4
烷基、或C1
-C4
烷氧基。甚至更較佳的是,每個R9
獨立地是C1
-C4
烷基。最較佳的是,每個R9
係甲基。
m係0、1或2的整數。較佳的是,m係0或2。
W充當連接基部分,將環系統D連接到分子的剩餘部分(即,連接到苯基-嗒𠯤酮/苯基-嗒𠯤二酮部分)。具有式 (I) 之化合物(其中連接基係W1和W3)係除草劑,而具有式 (I) 之化合物(其中連接基係W2)可以不僅是除草劑,還是可用於生產攜帶W1連接基的具有式 (I) 之化合物的中間體。因此,在一組實施方式中,W係W1或W3(較佳的是W1),而在第二組實施方式中,W係W2。
較佳的是,R10
、R11
、R12
和R13
各自獨立地選自氫或C1
-C3
烷基。在一組實施方式中,R10
、R11
、R12
和R13
皆為氫。
較佳的是,R14
和R15
各自獨立地選自氫或C1
-C3
烷基。在一組實施方式中,R14
和R15
皆為氫。
在一組較佳的實施方式中,在具有式 (I) 之化合物中,
R1
係甲基、乙基、環丙基、炔丙基或C1
氟烷基;
R2
係氯、環丙基、三氟甲基或甲基;
G係氫或-C(O)-R3
,其中R3
係異丙基、三級丁基、甲基、乙基、炔丙基、甲氧基、乙氧基、或三級丁氧基;
X係氟、氯或C1
-鹵代烷基並且相對於嗒𠯤酮/嗒𠯤-二酮部分係在鄰位;
Y係氫、氯、氟或溴並且相對於-W-D部分係在鄰位;
D係經取代或未經取代的萘環系統,或包含1、2、3或4個獨立地選自氧、氮和硫的雜原子的經取代或未經取代的8-10員二環飽和、部分飽和或不飽和的雜環系統,並且其中當D被取代時,其在至少一個環碳原子上被R8
取代和/或在至少一個環氮原子上被R9
取代;
每個R8
獨立地是羥基、鹵素、C1
-C6
烷基、C1
-C6
鹵代烷基或C1
-C6
烷氧基;
每個R9
獨立地是C1
-C4
烷基、或C1
-C4
烷氧基;
W係W1;並且
R10
、R11
、R12
和R13
皆為氫。
在一組甚至更較佳的實施方式中,在具有式 (I) 之化合物中,
R1
係甲基;
R2
係甲基;
G係氫或-C(O)-R3
,其中R3
係異丙基、三級丁基、甲基、乙基、炔丙基、甲氧基、乙氧基、或三級丁氧基;
X係氟並且相對於嗒𠯤酮/嗒𠯤-二酮部分係在鄰位;
Y係氯並且相對於-W-D部分係在鄰位;
D係經取代或未經取代的萘、吲口巾、吲哚、異吲哚、吲哚啉、異吲哚啉、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并㗁唑、苯并間二氧雜環戊烯、嘌呤、4H-喹口巾、喹啉、異喹啉、四氫喹啉、口辛啉、酞𠯤、喹㗁啉、1-8-口奈啶、喋啶、1H-吡咯并[2,3-b]吡啶、咪唑并[1,2-a]吡𠯤或1H-苯并三唑環系統,並且其中當D被取代時,其在一個或兩個環碳原子上被R8
取代和/或在一個環氮原子上被R9
取代;
每個R8
獨立地是C1
-C3
烷基、C1
-C3
鹵代烷基、氯、氟、羥基、或C1
-C3
烷氧基;
R9
係C1
-C4
烷基;
W係W1;並且
R10
、R11
、R12
和R13
皆為氫。
下表1至4說明了本發明之具有式 (I) 之化合物的2752種具體實例。
[ 表 1]
提供了688種具有如上示出的式 (I) 之化合物A-1.001至A-1.688,其中G係氫,W係-CH2
-CH2
-並且R1
、R2
、X、Y、D係如下表A中分別對於化合物編號1.001至1.688所定義的。
[
表
A]
具有式
(I)
之化合物的
R1
、
R2
、
X
、
Y
和
D
的取代基定義
化合物編號 | R1 | R2 | X | Y | D |
1.001 | -Me | -Me | 6-F | 3-F | 1,2,3,4-四氫喹啉-6-基- |
1.002 | -Me | -Me | 6-F | 3-F | 1H-吲哚-4-基- |
1.003 | -Me | -Me | 6-F | 3-F | 1H-吲哚-5-基- |
1.004 | -Me | -Me | 6-F | 3-F | 1H-吲哚-6-基- |
1.005 | -Me | -Me | 6-F | 3-F | 1-甲基吲哚-4-基- |
1.006 | -Me | -Me | 6-F | 3-F | 1-甲基吲哚-5-基- |
1.007 | -Me | -Me | 6-F | 3-F | 1-甲基吲哚-6-基- |
1.008 | -Me | -Me | 6-F | 3-F | 1-萘基- |
1.009 | -Me | -Me | 6-F | 3-F | 2-(三氟甲基)-4-喹啉基- |
1.010 | -Me | -Me | 6-F | 3-F | 2-乙基-1,3-苯并㗁唑-6-基- |
1.011 | -Me | -Me | 6-F | 3-F | 2-甲基-1,3-苯并㗁唑-6-基- |
1.012 | -Me | -Me | 6-F | 3-F | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.013 | -Me | -Me | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.014 | -Me | -Me | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.015 | -Me | -Me | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.016 | -Me | -Me | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.017 | -Me | -Me | 6-F | 3-F | 2-萘基- |
1.018 | -Me | -Me | 6-F | 3-F | 4-喹啉基- |
1.019 | -Me | -Me | 6-F | 3-Cl | 1,2,3,4-四氫喹啉-6-基- |
1.020 | -Me | -Me | 6-F | 3-Cl | 1H-吲哚-4-基- |
1.021 | -Me | -Me | 6-F | 3-Cl | 1H-吲哚-5-基- |
1.022 | -Me | -Me | 6-F | 3-Cl | 1H-吲哚-6-基- |
1.023 | -Me | -Me | 6-F | 3-Cl | 1-甲基吲哚-4-基- |
1.024 | -Me | -Me | 6-F | 3-Cl | 1-甲基吲哚-5-基- |
1.025 | -Me | -Me | 6-F | 3-Cl | 1-甲基吲哚-6-基- |
1.026 | -Me | -Me | 6-F | 3-Cl | 1-萘基- |
1.027 | -Me | -Me | 6-F | 3-Cl | 2-(三氟甲基)-4-喹啉基- |
1.028 | -Me | -Me | 6-F | 3-Cl | 2-乙基-1,3-苯并㗁唑-6-基- |
1.029 | -Me | -Me | 6-F | 3-Cl | 2-甲基-1,3-苯并㗁唑-6-基- |
1.030 | -Me | -Me | 6-F | 3-Cl | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.031 | -Me | -Me | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.032 | -Me | -Me | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.033 | -Me | -Me | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.034 | -Me | -Me | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.035 | -Me | -Me | 6-F | 3-Cl | 2-萘基- |
1.036 | -Me | -Me | 6-F | 3-Cl | 4-喹啉基- |
1.037 | -Me | -Me | 6-Cl | 3-F | 1,2,3,4-四氫喹啉-6-基- |
1.038 | -Me | -Me | 6-Cl | 3-F | 1H-吲哚-4-基- |
1.039 | -Me | -Me | 6-Cl | 3-F | 1H-吲哚-5-基- |
1.040 | -Me | -Me | 6-Cl | 3-F | 1H-吲哚-6-基- |
1.041 | -Me | -Me | 6-Cl | 3-F | 1-甲基吲哚-4-基- |
1.042 | -Me | -Me | 6-Cl | 3-F | 1-甲基吲哚-5-基- |
1.043 | -Me | -Me | 6-Cl | 3-F | 1-甲基吲哚-6-基- |
1.044 | -Me | -Me | 6-Cl | 3-F | 1-萘基- |
1.045 | -Me | -Me | 6-Cl | 3-F | 2-(三氟甲基)-4-喹啉基- |
1.046 | -Me | -Me | 6-Cl | 3-F | 2-乙基-1,3-苯并㗁唑-6-基- |
1.047 | -Me | -Me | 6-Cl | 3-F | 2-甲基-1,3-苯并㗁唑-6-基- |
1.048 | -Me | -Me | 6-Cl | 3-F | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.049 | -Me | -Me | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.050 | -Me | -Me | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.051 | -Me | -Me | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.052 | -Me | -Me | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.053 | -Me | -Me | 6-Cl | 3-F | 2-萘基- |
1.054 | -Me | -Me | 6-Cl | 3-F | 4-喹啉基- |
1.055 | -Me | -Me | 6-Cl | 3-Cl | 1,2,3,4-四氫喹啉-6-基- |
1.056 | -Me | -Me | 6-Cl | 3-Cl | 1H-吲哚-4-基- |
1.057 | -Me | -Me | 6-Cl | 3-Cl | 1H-吲哚-5-基- |
1.058 | -Me | -Me | 6-Cl | 3-Cl | 1H-吲哚-6-基- |
1.059 | -Me | -Me | 6-Cl | 3-Cl | 1-甲基吲哚-4-基- |
1.060 | -Me | -Me | 6-Cl | 3-Cl | 1-甲基吲哚-5-基- |
1.061 | -Me | -Me | 6-Cl | 3-Cl | 1-甲基吲哚-6-基- |
1.062 | -Me | -Me | 6-Cl | 3-Cl | 1-萘基- |
1.063 | -Me | -Me | 6-Cl | 3-Cl | 2-(三氟甲基)-4-喹啉基- |
1.064 | -Me | -Me | 6-Cl | 3-Cl | 2-乙基-1,3-苯并㗁唑-6-基- |
1.065 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-1,3-苯并㗁唑-6-基- |
1.066 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.067 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.068 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.069 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.070 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.071 | -Me | -Me | 6-Cl | 3-Cl | 2-萘基- |
1.072 | -Me | -Me | 6-Cl | 3-Cl | 4-喹啉基- |
1.073 | -Me | -Cl | 6-F | 3-F | 1,2,3,4-四氫喹啉-6-基- |
1.074 | -Me | -Cl | 6-F | 3-F | 1H-吲哚-4-基- |
1.075 | -Me | -Cl | 6-F | 3-F | 1H-吲哚-5-基- |
1.076 | -Me | -Cl | 6-F | 3-F | 1H-吲哚-6-基- |
1.077 | -Me | -Cl | 6-F | 3-F | 1-甲基吲哚-4-基- |
1.078 | -Me | -Cl | 6-F | 3-F | 1-甲基吲哚-5-基- |
1.079 | -Me | -Cl | 6-F | 3-F | 1-甲基吲哚-6-基- |
1.080 | -Me | -Cl | 6-F | 3-F | 1-萘基- |
1.081 | -Me | -Cl | 6-F | 3-F | 2-(三氟甲基)-4-喹啉基- |
1.082 | -Me | -Cl | 6-F | 3-F | 2-乙基-1,3-苯并㗁唑-6-基- |
1.083 | -Me | -Cl | 6-F | 3-F | 2-甲基-1,3-苯并㗁唑-6-基- |
1.084 | -Me | -Cl | 6-F | 3-F | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.085 | -Me | -Cl | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.086 | -Me | -Cl | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.087 | -Me | -Cl | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.088 | -Me | -Cl | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.089 | -Me | -Cl | 6-F | 3-F | 2-萘基- |
1.090 | -Me | -Cl | 6-F | 3-F | 4-喹啉基- |
1.091 | -Me | -Cl | 6-F | 3-Cl | 1,2,3,4-四氫喹啉-6-基- |
1.092 | -Me | -Cl | 6-F | 3-Cl | 1H-吲哚-4-基- |
1.093 | -Me | -Cl | 6-F | 3-Cl | 1H-吲哚-5-基- |
1.094 | -Me | -Cl | 6-F | 3-Cl | 1H-吲哚-6-基- |
1.095 | -Me | -Cl | 6-F | 3-Cl | 1-甲基吲哚-4-基- |
1.096 | -Me | -Cl | 6-F | 3-Cl | 1-甲基吲哚-5-基- |
1.097 | -Me | -Cl | 6-F | 3-Cl | 1-甲基吲哚-6-基- |
1.098 | -Me | -Cl | 6-F | 3-Cl | 1-萘基- |
1.099 | -Me | -Cl | 6-F | 3-Cl | 2-(三氟甲基)-4-喹啉基- |
1.100 | -Me | -Cl | 6-F | 3-Cl | 2-乙基-1,3-苯并㗁唑-6-基- |
1.101 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-1,3-苯并㗁唑-6-基- |
1.102 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.103 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.104 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.105 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.106 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.107 | -Me | -Cl | 6-F | 3-Cl | 2-萘基- |
1.108 | -Me | -Cl | 6-F | 3-Cl | 4-喹啉基- |
1.109 | -Me | -Cl | 6-Cl | 3-F | 1,2,3,4-四氫喹啉-6-基- |
1.110 | -Me | -Cl | 6-Cl | 3-F | 1H-吲哚-4-基- |
1.111 | -Me | -Cl | 6-Cl | 3-F | 1H-吲哚-5-基- |
1.112 | -Me | -Cl | 6-Cl | 3-F | 1H-吲哚-6-基- |
1.113 | -Me | -Cl | 6-Cl | 3-F | 1-甲基吲哚-4-基- |
1.114 | -Me | -Cl | 6-Cl | 3-F | 1-甲基吲哚-5-基- |
1.115 | -Me | -Cl | 6-Cl | 3-F | 1-甲基吲哚-6-基- |
1.116 | -Me | -Cl | 6-Cl | 3-F | 1-萘基- |
1.117 | -Me | -Cl | 6-Cl | 3-F | 2-(三氟甲基)-4-喹啉基- |
1.118 | -Me | -Cl | 6-Cl | 3-F | 2-乙基-1,3-苯并㗁唑-6-基- |
1.119 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-1,3-苯并㗁唑-6-基- |
1.120 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.121 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.122 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.123 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.124 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.125 | -Me | -Cl | 6-Cl | 3-F | 2-萘基- |
1.126 | -Me | -Cl | 6-Cl | 3-F | 4-喹啉基- |
1.127 | -Me | -Cl | 6-Cl | 3-Cl | 1,2,3,4-四氫喹啉-6-基- |
1.128 | -Me | -Cl | 6-Cl | 3-Cl | 1H-吲哚-4-基- |
1.129 | -Me | -Cl | 6-Cl | 3-Cl | 1H-吲哚-5-基- |
1.130 | -Me | -Cl | 6-Cl | 3-Cl | 1H-吲哚-6-基- |
1.131 | -Me | -Cl | 6-Cl | 3-Cl | 1-甲基吲哚-4-基- |
1.132 | -Me | -Cl | 6-Cl | 3-Cl | 1-甲基吲哚-5-基- |
1.133 | -Me | -Cl | 6-Cl | 3-Cl | 1-甲基吲哚-6-基- |
1.134 | -Me | -Cl | 6-Cl | 3-Cl | 1-萘基- |
1.135 | -Me | -Cl | 6-Cl | 3-Cl | 2-(三氟甲基)-4-喹啉基- |
1.136 | -Me | -Cl | 6-Cl | 3-Cl | 2-乙基-1,3-苯并㗁唑-6-基- |
1.137 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-1,3-苯并㗁唑-6-基- |
1.138 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.139 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.140 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.141 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.142 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.143 | -Me | -Cl | 6-Cl | 3-Cl | 2-萘基- |
1.144 | -Me | -Cl | 6-Cl | 3-Cl | 4-喹啉基- |
1.145 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1,2,3,4-四氫喹啉-6-基- |
1.146 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1H-吲哚-4-基- |
1.147 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1H-吲哚-5-基- |
1.148 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1H-吲哚-6-基- |
1.149 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1-甲基吲哚-4-基- |
1.150 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1-甲基吲哚-5-基- |
1.151 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1-甲基吲哚-6-基- |
1.152 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1-萘基- |
1.153 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-(三氟甲基)-4-喹啉基- |
1.154 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-乙基-1,3-苯并㗁唑-6-基- |
1.155 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-1,3-苯并㗁唑-6-基- |
1.156 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.157 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.158 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.159 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.160 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.161 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-萘基- |
1.162 | -CH2 -C≡CH | -Me | 6-F | 3-F | 4-喹啉基- |
1.163 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1,2,3,4-四氫喹啉-6-基- |
1.164 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1H-吲哚-4-基- |
1.165 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1H-吲哚-5-基- |
1.166 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1H-吲哚-6-基- |
1.167 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1-甲基吲哚-4-基- |
1.168 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1-甲基吲哚-5-基- |
1.169 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1-甲基吲哚-6-基- |
1.170 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1-萘基- |
1.171 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-(三氟甲基)-4-喹啉基- |
1.172 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-乙基-1,3-苯并㗁唑-6-基- |
1.173 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-1,3-苯并㗁唑-6-基- |
1.174 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.175 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.176 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.177 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.178 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.179 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-萘基- |
1.180 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 4-喹啉基- |
1.181 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1,2,3,4-四氫喹啉-6-基- |
1.182 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1H-吲哚-4-基- |
1.183 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1H-吲哚-5-基- |
1.184 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1H-吲哚-6-基- |
1.185 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1-甲基吲哚-4-基- |
1.186 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1-甲基吲哚-5-基- |
1.187 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1-甲基吲哚-6-基- |
1.188 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1-萘基- |
1.189 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-(三氟甲基)-4-喹啉基- |
1.190 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-乙基-1,3-苯并㗁唑-6-基- |
1.191 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-1,3-苯并㗁唑-6-基- |
1.192 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.193 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.194 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.195 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.196 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.197 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-萘基- |
1.198 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 4-喹啉基- |
1.199 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1,2,3,4-四氫喹啉-6-基- |
1.200 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1H-吲哚-4-基- |
1.201 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1H-吲哚-5-基- |
1.202 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1H-吲哚-6-基- |
1.203 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1-甲基吲哚-4-基- |
1.204 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1-甲基吲哚-5-基- |
1.205 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1-甲基吲哚-6-基- |
1.206 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1-萘基- |
1.207 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-(三氟甲基)-4-喹啉基- |
1.208 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-乙基-1,3-苯并㗁唑-6-基- |
1.209 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-1,3-苯并㗁唑-6-基- |
1.210 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.211 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.212 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.213 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.214 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.215 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-萘基- |
1.216 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 4-喹啉基- |
1.217 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1,2,3,4-四氫喹啉-6-基- |
1.218 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1H-吲哚-4-基- |
1.219 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1H-吲哚-5-基- |
1.220 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1H-吲哚-6-基- |
1.221 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1-甲基吲哚-4-基- |
1.222 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1-甲基吲哚-5-基- |
1.223 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1-甲基吲哚-6-基- |
1.224 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1-萘基- |
1.225 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-(三氟甲基)-4-喹啉基- |
1.226 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-乙基-1,3-苯并㗁唑-6-基- |
1.227 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-1,3-苯并㗁唑-6-基- |
1.228 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.229 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.230 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.231 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.232 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-6-喹啉基- |
1.233 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-萘基- |
1.234 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 4-喹啉基- |
1.235 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1,2,3,4-四氫喹啉-6-基- |
1.236 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1H-吲哚-4-基- |
1.237 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1H-吲哚-5-基- |
1.238 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1H-吲哚-6-基- |
1.239 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1-甲基吲哚-4-基- |
1.240 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1-甲基吲哚-5-基- |
1.241 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1-甲基吲哚-6-基- |
1.242 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1-萘基- |
1.243 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-(三氟甲基)-4-喹啉基- |
1.244 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-乙基-1,3-苯并㗁唑-6-基- |
1.245 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-1,3-苯并㗁唑-6-基- |
1.246 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.247 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.248 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.249 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.250 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-6-喹啉基- |
1.251 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-萘基- |
1.252 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 4-喹啉基- |
1.253 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1,2,3,4-四氫喹啉-6-基- |
1.254 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1H-吲哚-4-基- |
1.255 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1H-吲哚-5-基- |
1.256 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1H-吲哚-6-基- |
1.257 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1-甲基吲哚-4-基- |
1.258 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1-甲基吲哚-5-基- |
1.259 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1-甲基吲哚-6-基- |
1.260 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1-萘基- |
1.261 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-(三氟甲基)-4-喹啉基- |
1.262 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-乙基-1,3-苯并㗁唑-6-基- |
1.263 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-1,3-苯并㗁唑-6-基- |
1.264 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.265 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.266 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.267 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.268 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-6-喹啉基- |
1.269 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-萘基- |
1.270 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 4-喹啉基- |
1.271 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1,2,3,4-四氫喹啉-6-基- |
1.272 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1H-吲哚-4-基- |
1.273 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1H-吲哚-5-基- |
1.274 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1H-吲哚-6-基- |
1.275 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1-甲基吲哚-4-基- |
1.276 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1-甲基吲哚-5-基- |
1.277 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1-甲基吲哚-6-基- |
1.278 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1-萘基- |
1.279 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-(三氟甲基)-4-喹啉基- |
1.280 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-乙基-1,3-苯并㗁唑-6-基- |
1.281 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-1,3-苯并㗁唑-6-基- |
1.282 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-1,2,3,4-四氫喹啉-6-基- |
1.283 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.284 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.285 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.286 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-6-喹啉基- |
1.287 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-萘基- |
1.288 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 4-喹啉基- |
1.289 | -Me | -Me | 6-F | 3-F | 2-甲基-5-1,3-苯并噻唑基- |
1.290 | -Me | -Me | 6-F | 3-F | 2,2-二甲基-6-3H-苯并呋喃基- |
1.291 | -Me | -Me | 6-F | 3-F | 2-甲基-6-1,3-苯并㗁唑基- |
1.292 | -Me | -Me | 6-F | 3-F | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.293 | -Me | -Me | 6-F | 3-F | 3-甲基-5-苯并三唑基- |
1.294 | -Me | -Me | 6-F | 3-F | 1-甲基-3-吲唑基- |
1.295 | -Me | -Me | 6-F | 3-F | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.296 | -Me | -Me | 6-F | 3-F | 5-苯并呋喃基- |
1.297 | -Me | -Me | 6-F | 3-F | 6-苯并噻吩基- |
1.298 | -Me | -Me | 6-F | 3-F | 5-苯并噻吩基- |
1.299 | -Me | -Me | 6-F | 3-F | 6-1,3-苯并噻唑基- |
1.300 | -Me | -Me | 6-F | 3-F | 5-1,3-苯并噻唑基- |
1.301 | -Me | -Me | 6-F | 3-F | 3-甲基-6-1,2-苯并㗁唑基- |
1.302 | -Me | -Me | 6-F | 3-F | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.303 | -Me | -Me | 6-F | 3-F | 6-1-甲基吲唑基- |
1.304 | -Me | -Me | 6-F | 3-F | 5-1-甲基吲唑基- |
1.305 | -Me | -Me | 6-F | 3-F | 6-1-甲基吲哚基- |
1.306 | -Me | -Me | 6-F | 3-F | 5-1-甲基吲哚基- |
1.307 | -Me | -Me | 6-F | 3-F | 5-2-側氧基吲哚啉基- |
1.308 | -Me | -Me | 6-F | 3-F | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.309 | -Me | -Me | 6-F | 3-F | 2-1,3-苯并㗁唑基- |
1.310 | -Me | -Me | 6-F | 3-F | 2-1,3-苯并噻唑基 |
1.311 | -Me | -Me | 6-F | 3-F | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.312 | -Me | -Me | 6-F | 3-F | 6-2,2-二甲基-3H-苯并呋喃基- |
1.313 | -Me | -Me | 6-F | 3-F | 6-咪唑并[1,2-a]吡𠯤基- |
1.314 | -Me | -Me | 6-F | 3-Cl | 2-甲基-5-1,3-苯并噻唑基- |
1.315 | -Me | -Me | 6-F | 3-Cl | 2,2-二甲基-6-3H-苯并呋喃基- |
1.316 | -Me | -Me | 6-F | 3-Cl | 2-甲基-6-1,3-苯并㗁唑基- |
1.317 | -Me | -Me | 6-F | 3-Cl | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.318 | -Me | -Me | 6-F | 3-Cl | 3-甲基-5-苯并三唑基- |
1.319 | -Me | -Me | 6-F | 3-Cl | 1-甲基-3-吲唑基- |
1.320 | -Me | -Me | 6-F | 3-Cl | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.321 | -Me | -Me | 6-F | 3-Cl | 5-苯并呋喃基- |
1.322 | -Me | -Me | 6-F | 3-Cl | 6-苯并噻吩基- |
1.323 | -Me | -Me | 6-F | 3-Cl | 5-苯并噻吩基- |
1.324 | -Me | -Me | 6-F | 3-Cl | 6-1,3-苯并噻唑基- |
1.325 | -Me | -Me | 6-F | 3-Cl | 5-1,3-苯并噻唑基- |
1.326 | -Me | -Me | 6-F | 3-Cl | 3-甲基-6-1,2-苯并㗁唑基- |
1.327 | -Me | -Me | 6-F | 3-Cl | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.328 | -Me | -Me | 6-F | 3-Cl | 6-1-甲基吲唑基- |
1.329 | -Me | -Me | 6-F | 3-Cl | 5-1-甲基吲唑基- |
1.330 | -Me | -Me | 6-F | 3-Cl | 6-1-甲基吲哚基- |
1.331 | -Me | -Me | 6-F | 3-Cl | 5-1-甲基吲哚基- |
1.332 | -Me | -Me | 6-F | 3-Cl | 5-2-側氧基吲哚啉基- |
1.333 | -Me | -Me | 6-F | 3-Cl | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.334 | -Me | -Me | 6-F | 3-Cl | 2-1,3-苯并㗁唑基- |
1.335 | -Me | -Me | 6-F | 3-Cl | 2-1,3-苯并噻唑基 |
1.336 | -Me | -Me | 6-F | 3-Cl | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.337 | -Me | -Me | 6-F | 3-Cl | 6-2,2-二甲基-3H-苯并呋喃基- |
1.338 | -Me | -Me | 6-F | 3-Cl | 6-咪唑并[1,2-a]吡𠯤基- |
1.339 | -Me | -Me | 6-Cl | 3-F | 2-甲基-5-1,3-苯并噻唑基- |
1.340 | -Me | -Me | 6-Cl | 3-F | 2,2-二甲基-6-3H-苯并呋喃基- |
1.341 | -Me | -Me | 6-Cl | 3-F | 2-甲基-6-1,3-苯并㗁唑基- |
1.342 | -Me | -Me | 6-Cl | 3-F | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.343 | -Me | -Me | 6-Cl | 3-F | 3-甲基-5-苯并三唑基- |
1.344 | -Me | -Me | 6-Cl | 3-F | 1-甲基-3-吲唑基- |
1.345 | -Me | -Me | 6-Cl | 3-F | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.346 | -Me | -Me | 6-Cl | 3-F | 5-苯并呋喃基- |
1.347 | -Me | -Me | 6-Cl | 3-F | 6-苯并噻吩基- |
1.348 | -Me | -Me | 6-Cl | 3-F | 5-苯并噻吩基- |
1.349 | -Me | -Me | 6-Cl | 3-F | 6-1,3-苯并噻唑基- |
1.350 | -Me | -Me | 6-Cl | 3-F | 5-1,3-苯并噻唑基- |
1.351 | -Me | -Me | 6-Cl | 3-F | 3-甲基-6-1,2-苯并㗁唑基- |
1.352 | -Me | -Me | 6-Cl | 3-F | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.353 | -Me | -Me | 6-Cl | 3-F | 6-1-甲基吲唑基- |
1.354 | -Me | -Me | 6-Cl | 3-F | 5-1-甲基吲唑基- |
1.355 | -Me | -Me | 6-Cl | 3-F | 6-1-甲基吲哚基- |
1.356 | -Me | -Me | 6-Cl | 3-F | 5-1-甲基吲哚基- |
1.357 | -Me | -Me | 6-Cl | 3-F | 5-2-側氧基吲哚啉基- |
1.358 | -Me | -Me | 6-Cl | 3-F | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.359 | -Me | -Me | 6-Cl | 3-F | 2-1,3-苯并㗁唑基- |
1.360 | -Me | -Me | 6-Cl | 3-F | 2-1,3-苯并噻唑基 |
1.361 | -Me | -Me | 6-Cl | 3-F | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.362 | -Me | -Me | 6-Cl | 3-F | 6-2,2-二甲基-3H-苯并呋喃基- |
1.363 | -Me | -Me | 6-Cl | 3-F | 6-咪唑并[1,2-a]吡𠯤基- |
1.364 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-5-1,3-苯并噻唑基- |
1.365 | -Me | -Me | 6-Cl | 3-Cl | 2,2-二甲基-6-3H-苯并呋喃基- |
1.366 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-6-1,3-苯并㗁唑基- |
1.367 | -Me | -Me | 6-Cl | 3-Cl | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.368 | -Me | -Me | 6-Cl | 3-Cl | 3-甲基-5-苯并三唑基- |
1.369 | -Me | -Me | 6-Cl | 3-Cl | 1-甲基-3-吲唑基- |
1.370 | -Me | -Me | 6-Cl | 3-Cl | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.371 | -Me | -Me | 6-Cl | 3-Cl | 5-苯并呋喃基- |
1.372 | -Me | -Me | 6-Cl | 3-Cl | 6-苯并噻吩基- |
1.373 | -Me | -Me | 6-Cl | 3-Cl | 5-苯并噻吩基- |
1.374 | -Me | -Me | 6-Cl | 3-Cl | 6-1,3-苯并噻唑基- |
1.375 | -Me | -Me | 6-Cl | 3-Cl | 5-1,3-苯并噻唑基- |
1.376 | -Me | -Me | 6-Cl | 3-Cl | 3-甲基-6-1,2-苯并㗁唑基- |
1.377 | -Me | -Me | 6-Cl | 3-Cl | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.378 | -Me | -Me | 6-Cl | 3-Cl | 6-1-甲基吲唑基- |
1.379 | -Me | -Me | 6-Cl | 3-Cl | 5-1-甲基吲唑基- |
1.380 | -Me | -Me | 6-Cl | 3-Cl | 6-1-甲基吲哚基- |
1.381 | -Me | -Me | 6-Cl | 3-Cl | 5-1-甲基吲哚基- |
1.382 | -Me | -Me | 6-Cl | 3-Cl | 5-2-側氧基吲哚啉基- |
1.383 | -Me | -Me | 6-Cl | 3-Cl | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.384 | -Me | -Me | 6-Cl | 3-Cl | 2-1,3-苯并㗁唑基- |
1.385 | -Me | -Me | 6-Cl | 3-Cl | 2-1,3-苯并噻唑基 |
1.386 | -Me | -Me | 6-Cl | 3-Cl | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.387 | -Me | -Me | 6-Cl | 3-Cl | 6-2,2-二甲基-3H-苯并呋喃基- |
1.388 | -Me | -Me | 6-Cl | 3-Cl | 6-咪唑并[1,2-a]吡𠯤基- |
1.389 | -Me | -Cl | 6-F | 3-F | 2-甲基-5-1,3-苯并噻唑基- |
1.390 | -Me | -Cl | 6-F | 3-F | 2,2-二甲基-6-3H-苯并呋喃基- |
1.391 | -Me | -Cl | 6-F | 3-F | 2-甲基-6-1,3-苯并㗁唑基- |
1.392 | -Me | -Cl | 6-F | 3-F | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.393 | -Me | -Cl | 6-F | 3-F | 3-甲基-5-苯并三唑基- |
1.394 | -Me | -Cl | 6-F | 3-F | 1-甲基-3-吲唑基- |
1.395 | -Me | -Cl | 6-F | 3-F | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.396 | -Me | -Cl | 6-F | 3-F | 5-苯并呋喃基- |
1.397 | -Me | -Cl | 6-F | 3-F | 6-苯并噻吩基- |
1.398 | -Me | -Cl | 6-F | 3-F | 5-苯并噻吩基- |
1.399 | -Me | -Cl | 6-F | 3-F | 6-1,3-苯并噻唑基- |
1.400 | -Me | -Cl | 6-F | 3-F | 5-1,3-苯并噻唑基- |
1.401 | -Me | -Cl | 6-F | 3-F | 3-甲基-6-1,2-苯并㗁唑基- |
1.402 | -Me | -Cl | 6-F | 3-F | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.403 | -Me | -Cl | 6-F | 3-F | 6-1-甲基吲唑基- |
1.404 | -Me | -Cl | 6-F | 3-F | 5-1-甲基吲唑基- |
1.405 | -Me | -Cl | 6-F | 3-F | 6-1-甲基吲哚基- |
1.406 | -Me | -Cl | 6-F | 3-F | 5-1-甲基吲哚基- |
1.407 | -Me | -Cl | 6-F | 3-F | 5-2-側氧基吲哚啉基- |
1.408 | -Me | -Cl | 6-F | 3-F | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.409 | -Me | -Cl | 6-F | 3-F | 2-1,3-苯并㗁唑基- |
1.410 | -Me | -Cl | 6-F | 3-F | 2-1,3-苯并噻唑基 |
1.411 | -Me | -Cl | 6-F | 3-F | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.412 | -Me | -Cl | 6-F | 3-F | 6-2,2-二甲基-3H-苯并呋喃基- |
1.413 | -Me | -Cl | 6-F | 3-F | 6-咪唑并[1,2-a]吡𠯤基- |
1.414 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-5-1,3-苯并噻唑基- |
1.415 | -Me | -Cl | 6-F | 3-Cl | 2,2-二甲基-6-3H-苯并呋喃基- |
1.416 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-6-1,3-苯并㗁唑基- |
1.417 | -Me | -Cl | 6-F | 3-Cl | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.418 | -Me | -Cl | 6-F | 3-Cl | 3-甲基-5-苯并三唑基- |
1.419 | -Me | -Cl | 6-F | 3-Cl | 1-甲基-3-吲唑基- |
1.420 | -Me | -Cl | 6-F | 3-Cl | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.421 | -Me | -Cl | 6-F | 3-Cl | 5-苯并呋喃基- |
1.422 | -Me | -Cl | 6-F | 3-Cl | 6-苯并噻吩基- |
1.423 | -Me | -Cl | 6-F | 3-Cl | 5-苯并噻吩基- |
1.424 | -Me | -Cl | 6-F | 3-Cl | 6-1,3-苯并噻唑基- |
1.425 | -Me | -Cl | 6-F | 3-Cl | 5-1,3-苯并噻唑基- |
1.426 | -Me | -Cl | 6-F | 3-Cl | 3-甲基-6-1,2-苯并㗁唑基- |
1.427 | -Me | -Cl | 6-F | 3-Cl | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.428 | -Me | -Cl | 6-F | 3-Cl | 6-1-甲基吲唑基- |
1.429 | -Me | -Cl | 6-F | 3-Cl | 5-1-甲基吲唑基- |
1.430 | -Me | -Cl | 6-F | 3-Cl | 6-1-甲基吲哚基- |
1.431 | -Me | -Cl | 6-F | 3-Cl | 5-1-甲基吲哚基- |
1.432 | -Me | -Cl | 6-F | 3-Cl | 5-2-側氧基吲哚啉基- |
1.433 | -Me | -Cl | 6-F | 3-Cl | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.434 | -Me | -Cl | 6-F | 3-Cl | 2-1,3-苯并㗁唑基- |
1.435 | -Me | -Cl | 6-F | 3-Cl | 2-1,3-苯并噻唑基 |
1.436 | -Me | -Cl | 6-F | 3-Cl | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.437 | -Me | -Cl | 6-F | 3-Cl | 6-2,2-二甲基-3H-苯并呋喃基- |
1.438 | -Me | -Cl | 6-F | 3-Cl | 6-咪唑并[1,2-a]吡𠯤基- |
1.439 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-5-1,3-苯并噻唑基- |
1.440 | -Me | -Cl | 6-Cl | 3-F | 2,2-二甲基-6-3H-苯并呋喃基- |
1.441 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-6-1,3-苯并㗁唑基- |
1.442 | -Me | -Cl | 6-Cl | 3-F | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.443 | -Me | -Cl | 6-Cl | 3-F | 3-甲基-5-苯并三唑基- |
1.444 | -Me | -Cl | 6-Cl | 3-F | 1-甲基-3-吲唑基- |
1.445 | -Me | -Cl | 6-Cl | 3-F | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.446 | -Me | -Cl | 6-Cl | 3-F | 5-苯并呋喃基- |
1.447 | -Me | -Cl | 6-Cl | 3-F | 6-苯并噻吩基- |
1.448 | -Me | -Cl | 6-Cl | 3-F | 5-苯并噻吩基- |
1.449 | -Me | -Cl | 6-Cl | 3-F | 6-1,3-苯并噻唑基- |
1.450 | -Me | -Cl | 6-Cl | 3-F | 5-1,3-苯并噻唑基- |
1.451 | -Me | -Cl | 6-Cl | 3-F | 3-甲基-6-1,2-苯并㗁唑基- |
1.452 | -Me | -Cl | 6-Cl | 3-F | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.453 | -Me | -Cl | 6-Cl | 3-F | 6-1-甲基吲唑基- |
1.454 | -Me | -Cl | 6-Cl | 3-F | 5-1-甲基吲唑基- |
1.455 | -Me | -Cl | 6-Cl | 3-F | 6-1-甲基吲哚基- |
1.456 | -Me | -Cl | 6-Cl | 3-F | 5-1-甲基吲哚基- |
1.457 | -Me | -Cl | 6-Cl | 3-F | 5-2-側氧基吲哚啉基- |
1.458 | -Me | -Cl | 6-Cl | 3-F | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.459 | -Me | -Cl | 6-Cl | 3-F | 2-1,3-苯并㗁唑基- |
1.460 | -Me | -Cl | 6-Cl | 3-F | 2-1,3-苯并噻唑基 |
1.461 | -Me | -Cl | 6-Cl | 3-F | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.462 | -Me | -Cl | 6-Cl | 3-F | 6-2,2-二甲基-3H-苯并呋喃基- |
1.463 | -Me | -Cl | 6-Cl | 3-F | 6-咪唑并[1,2-a]吡𠯤基- |
1.464 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-5-1,3-苯并噻唑基- |
1.465 | -Me | -Cl | 6-Cl | 3-Cl | 2,2-二甲基-6-3H-苯并呋喃基- |
1.466 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-6-1,3-苯并㗁唑基- |
1.467 | -Me | -Cl | 6-Cl | 3-Cl | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.468 | -Me | -Cl | 6-Cl | 3-Cl | 3-甲基-5-苯并三唑基- |
1.469 | -Me | -Cl | 6-Cl | 3-Cl | 1-甲基-3-吲唑基- |
1.470 | -Me | -Cl | 6-Cl | 3-Cl | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.471 | -Me | -Cl | 6-Cl | 3-Cl | 5-苯并呋喃基- |
1.472 | -Me | -Cl | 6-Cl | 3-Cl | 6-苯并噻吩基- |
1.473 | -Me | -Cl | 6-Cl | 3-Cl | 5-苯并噻吩基- |
1.474 | -Me | -Cl | 6-Cl | 3-Cl | 6-1,3-苯并噻唑基- |
1.475 | -Me | -Cl | 6-Cl | 3-Cl | 5-1,3-苯并噻唑基- |
1.476 | -Me | -Cl | 6-Cl | 3-Cl | 3-甲基-6-1,2-苯并㗁唑基- |
1.477 | -Me | -Cl | 6-Cl | 3-Cl | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.478 | -Me | -Cl | 6-Cl | 3-Cl | 6-1-甲基吲唑基- |
1.479 | -Me | -Cl | 6-Cl | 3-Cl | 5-1-甲基吲唑基- |
1.480 | -Me | -Cl | 6-Cl | 3-Cl | 6-1-甲基吲哚基- |
1.481 | -Me | -Cl | 6-Cl | 3-Cl | 5-1-甲基吲哚基- |
1.482 | -Me | -Cl | 6-Cl | 3-Cl | 5-2-側氧基吲哚啉基- |
1.483 | -Me | -Cl | 6-Cl | 3-Cl | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.484 | -Me | -Cl | 6-Cl | 3-Cl | 2-1,3-苯并㗁唑基- |
1.485 | -Me | -Cl | 6-Cl | 3-Cl | 2-1,3-苯并噻唑基 |
1.486 | -Me | -Cl | 6-Cl | 3-Cl | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.487 | -Me | -Cl | 6-Cl | 3-Cl | 6-2,2-二甲基-3H-苯并呋喃基- |
1.488 | -Me | -Cl | 6-Cl | 3-Cl | 6-咪唑并[1,2-a]吡𠯤基- |
1.489 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-5-1,3-苯并噻唑基- |
1.490 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2,2-二甲基-6-3H-苯并呋喃基- |
1.491 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-6-1,3-苯并㗁唑基- |
1.492 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.493 | -CH2 -C≡CH | -Me | 6-F | 3-F | 3-甲基-5-苯并三唑基- |
1.494 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1-甲基-3-吲唑基- |
1.495 | -CH2 -C≡CH | -Me | 6-F | 3-F | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.496 | -CH2 -C≡CH | -Me | 6-F | 3-F | 5-苯并呋喃基- |
1.497 | -CH2 -C≡CH | -Me | 6-F | 3-F | 6-苯并噻吩基- |
1.498 | -CH2 -C≡CH | -Me | 6-F | 3-F | 5-苯并噻吩基- |
1.499 | -CH2 -C≡CH | -Me | 6-F | 3-F | 6-1,3-苯并噻唑基- |
1.500 | -CH2 -C≡CH | -Me | 6-F | 3-F | 5-1,3-苯并噻唑基- |
1.501 | -CH2 -C≡CH | -Me | 6-F | 3-F | 3-甲基-6-1,2-苯并㗁唑基- |
1.502 | -CH2 -C≡CH | -Me | 6-F | 3-F | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.503 | -CH2 -C≡CH | -Me | 6-F | 3-F | 6-1-甲基吲唑基- |
1.504 | -CH2 -C≡CH | -Me | 6-F | 3-F | 5-1-甲基吲唑基- |
1.505 | -CH2 -C≡CH | -Me | 6-F | 3-F | 6-1-甲基吲哚基- |
1.506 | -CH2 -C≡CH | -Me | 6-F | 3-F | 5-1-甲基吲哚基- |
1.507 | -CH2 -C≡CH | -Me | 6-F | 3-F | 5-2-側氧基吲哚啉基- |
1.508 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.509 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-1,3-苯并㗁唑基- |
1.510 | -CH2 -C≡CH | -Me | 6-F | 3-F | 2-1,3-苯并噻唑基 |
1.511 | -CH2 -C≡CH | -Me | 6-F | 3-F | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.512 | -CH2 -C≡CH | -Me | 6-F | 3-F | 6-2,2-二甲基-3H-苯并呋喃基- |
1.513 | -CH2 -C≡CH | -Me | 6-F | 3-F | 6-咪唑并[1,2-a]吡𠯤基- |
1.514 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-5-1,3-苯并噻唑基- |
1.515 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2,2-二甲基-6-3H-苯并呋喃基- |
1.516 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-6-1,3-苯并㗁唑基- |
1.517 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.518 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 3-甲基-5-苯并三唑基- |
1.519 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1-甲基-3-吲唑基- |
1.520 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.521 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 5-苯并呋喃基- |
1.522 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 6-苯并噻吩基- |
1.523 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 5-苯并噻吩基- |
1.524 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 6-1,3-苯并噻唑基- |
1.525 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 5-1,3-苯并噻唑基- |
1.526 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 3-甲基-6-1,2-苯并㗁唑基- |
1.527 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.528 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 6-1-甲基吲唑基- |
1.529 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 5-1-甲基吲唑基- |
1.530 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 6-1-甲基吲哚基- |
1.531 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 5-1-甲基吲哚基- |
1.532 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 5-2-側氧基吲哚啉基- |
1.533 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.534 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-1,3-苯并㗁唑基- |
1.535 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 2-1,3-苯并噻唑基 |
1.536 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.537 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 6-2,2-二甲基-3H-苯并呋喃基- |
1.538 | -CH2 -C≡CH | -Me | 6-F | 3-Cl | 6-咪唑并[1,2-a]吡𠯤基- |
1.539 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-5-1,3-苯并噻唑基- |
1.540 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2,2-二甲基-6-3H-苯并呋喃基- |
1.541 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-6-1,3-苯并㗁唑基- |
1.542 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.543 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 3-甲基-5-苯并三唑基- |
1.544 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1-甲基-3-吲唑基- |
1.545 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.546 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 5-苯并呋喃基- |
1.547 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 6-苯并噻吩基- |
1.548 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 5-苯并噻吩基- |
1.549 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 6-1,3-苯并噻唑基- |
1.550 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 5-1,3-苯并噻唑基- |
1.551 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 3-甲基-6-1,2-苯并㗁唑基- |
1.552 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.553 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 6-1-甲基吲唑基- |
1.554 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 5-1-甲基吲唑基- |
1.555 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 6-1-甲基吲哚基- |
1.556 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 5-1-甲基吲哚基- |
1.557 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 5-2-側氧基吲哚啉基- |
1.558 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.559 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-1,3-苯并㗁唑基- |
1.560 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 2-1,3-苯并噻唑基 |
1.561 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.562 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 6-2,2-二甲基-3H-苯并呋喃基- |
1.563 | -CH2 -C≡CH | -Me | 6-Cl | 3-F | 6-咪唑并[1,2-a]吡𠯤基- |
1.564 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-5-1,3-苯并噻唑基- |
1.565 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2,2-二甲基-6-3H-苯并呋喃基- |
1.566 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-6-1,3-苯并㗁唑基- |
1.567 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.568 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 3-甲基-5-苯并三唑基- |
1.569 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1-甲基-3-吲唑基- |
1.570 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.571 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 5-苯并呋喃基- |
1.572 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 6-苯并噻吩基- |
1.573 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 5-苯并噻吩基- |
1.574 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 6-1,3-苯并噻唑基- |
1.575 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 5-1,3-苯并噻唑基- |
1.576 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 3-甲基-6-1,2-苯并㗁唑基- |
1.577 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.578 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 6-1-甲基吲唑基- |
1.579 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 5-1-甲基吲唑基- |
1.580 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 6-1-甲基吲哚基- |
1.581 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 5-1-甲基吲哚基- |
1.582 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 5-2-側氧基吲哚啉基- |
1.583 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.584 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-1,3-苯并㗁唑基- |
1.585 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 2-1,3-苯并噻唑基 |
1.586 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.587 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 6-2,2-二甲基-3H-苯并呋喃基- |
1.588 | -CH2 -C≡CH | -Me | 6-Cl | 3-Cl | 6-咪唑并[1,2-a]吡𠯤基- |
1.589 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-5-1,3-苯并噻唑基- |
1.590 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2,2-二甲基-6-3H-苯并呋喃基- |
1.591 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-6-1,3-苯并㗁唑基- |
1.592 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.593 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 3-甲基-5-苯并三唑基- |
1.594 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1-甲基-3-吲唑基- |
1.595 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.596 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 5-苯并呋喃基- |
1.597 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 6-苯并噻吩基- |
1.598 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 5-苯并噻吩基- |
1.599 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 6-1,3-苯并噻唑基- |
1.600 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 5-1,3-苯并噻唑基- |
1.601 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 3-甲基-6-1,2-苯并㗁唑基- |
1.602 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.603 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 6-1-甲基吲唑基- |
1.604 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 5-1-甲基吲唑基- |
1.605 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 6-1-甲基吲哚基- |
1.606 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 5-1-甲基吲哚基- |
1.607 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 5-2-側氧基吲哚啉基- |
1.608 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.609 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-1,3-苯并㗁唑基- |
1.610 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 2-1,3-苯并噻唑基 |
1.611 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.612 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 6-2,2-二甲基-3H-苯并呋喃基- |
1.613 | -CH2 -C≡CH | -Cl | 6-F | 3-F | 6-咪唑并[1,2-a]吡𠯤基- |
1.614 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-5-1,3-苯并噻唑基- |
1.615 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2,2-二甲基-6-3H-苯并呋喃基- |
1.616 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-6-1,3-苯并㗁唑基- |
1.617 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.618 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 3-甲基-5-苯并三唑基- |
1.619 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1-甲基-3-吲唑基- |
1.620 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.621 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 5-苯并呋喃基- |
1.622 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 6-苯并噻吩基- |
1.623 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 5-苯并噻吩基- |
1.624 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 6-1,3-苯并噻唑基- |
1.625 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 5-1,3-苯并噻唑基- |
1.626 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 3-甲基-6-1,2-苯并㗁唑基- |
1.627 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.628 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 6-1-甲基吲唑基- |
1.629 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 5-1-甲基吲唑基- |
1.630 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 6-1-甲基吲哚基- |
1.631 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 5-1-甲基吲哚基- |
1.632 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 5-2-側氧基吲哚啉基- |
1.633 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.634 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-1,3-苯并㗁唑基- |
1.635 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 2-1,3-苯并噻唑基 |
1.636 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.637 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 6-2,2-二甲基-3H-苯并呋喃基- |
1.638 | -CH2 -C≡CH | -Cl | 6-F | 3-Cl | 6-咪唑并[1,2-a]吡𠯤基- |
1.639 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-5-1,3-苯并噻唑基- |
1.640 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2,2-二甲基-6-3H-苯并呋喃基- |
1.641 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-6-1,3-苯并㗁唑基- |
1.642 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.643 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 3-甲基-5-苯并三唑基- |
1.644 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1-甲基-3-吲唑基- |
1.645 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.646 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 5-苯并呋喃基- |
1.647 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 6-苯并噻吩基- |
1.648 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 5-苯并噻吩基- |
1.649 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 6-1,3-苯并噻唑基- |
1.650 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 5-1,3-苯并噻唑基- |
1.651 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 3-甲基-6-1,2-苯并㗁唑基- |
1.652 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.653 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 6-1-甲基吲唑基- |
1.654 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 5-1-甲基吲唑基- |
1.655 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 6-1-甲基吲哚基- |
1.656 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 5-1-甲基吲哚基- |
1.657 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 5-2-側氧基吲哚啉基- |
1.658 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.659 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-1,3-苯并㗁唑基- |
1.660 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 2-1,3-苯并噻唑基 |
1.661 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.662 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 6-2,2-二甲基-3H-苯并呋喃基- |
1.663 | -CH2 -C≡CH | -Cl | 6-Cl | 3-F | 6-咪唑并[1,2-a]吡𠯤基- |
1.664 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-5-1,3-苯并噻唑基- |
1.665 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2,2-二甲基-6-3H-苯并呋喃基- |
1.666 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-6-1,3-苯并㗁唑基- |
1.667 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- |
1.668 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 3-甲基-5-苯并三唑基- |
1.669 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1-甲基-3-吲唑基- |
1.670 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 1-甲基-5-吡咯并[2,3-b]吡啶基- |
1.671 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 5-苯并呋喃基- |
1.672 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 6-苯并噻吩基- |
1.673 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 5-苯并噻吩基- |
1.674 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 6-1,3-苯并噻唑基- |
1.675 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 5-1,3-苯并噻唑基- |
1.676 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 3-甲基-6-1,2-苯并㗁唑基- |
1.677 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 5-2-側氧基-3H-1,3-苯并㗁唑基- |
1.678 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 6-1-甲基吲唑基- |
1.679 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 5-1-甲基吲唑基- |
1.680 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 6-1-甲基吲哚基- |
1.681 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 5-1-甲基吲哚基- |
1.682 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 5-2-側氧基吲哚啉基- |
1.683 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-甲基-1,3-二側氧基-異吲哚啉-5-基 |
1.684 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-1,3-苯并㗁唑基- |
1.685 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 2-1,3-苯并噻唑基 |
1.686 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 5-2,2-二甲基-1,3-苯并間二氧雜環戊烯基- |
1.687 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 6-2,2-二甲基-3H-苯并呋喃基- |
1.688 | -CH2 -C≡CH | -Cl | 6-Cl | 3-Cl | 6-咪唑并[1,2-a]吡𠯤基- |
[ 表 2]
提供了688種具有如上示出的式 (I) 之化合物A-2.001至A-2.688,其中G係氫,W係 (E)-CH=CH-並且R1
、R2
、X、Y、D係如上表A中分別對於化合物編號1.001至1.688所定義的。
[ 表 3]
提供了688種具有如上示出的式 (I) 之化合物A-3.001至A-3.688,其中G係-(C=O)iPr,W係-CH2
-CH2
-並且R1
、R2
、X、Y、D係如上表A中分別對於化合物編號1.001至1.288所定義的。
[ 表 4]
提供了688種具有如上示出的式 (I) 之化合物A-4.001至A-4.688,其中G係-(C=O)iPr,W係 (E)-CH=CH-並且R1
、R2
、X、Y、D係如上表A中分別對於化合物編號1.001至1.288所定義的。
本發明之化合物可以根據以下流程製備,其中取代基R1
、R2
、R3
、R4
、R5
、R6
、R8
、R9
、R10
、R11
、R12
、R13
、R14
、R15
、R16
、W、D、G、X、Y、Z和m具有(除非另外明確說明)在上文中所述之定義。
如在反應流程 1
中所示,可以由化合物 (2) 製備本發明之某些化合物 (I-ii)。化合物 (I-ii) 係具有式 (I) 之化合物,其中W係-CH2
-CH2
-。
化合物 (I-ii) 可以藉由化合物 (2) 與氫氣在合適的溶劑 [如四氫呋喃、甲醇、乙醇、乙酸或乙酸乙酯] 中在合適的催化劑 [如Pd/C、Pd/CaCO3
、Rh/Al2
CO3
或海綿鎳] 存在下在-10°C與100°C之間的溫度下的催化氫化來製備。
可替代地,化合物 (I-ii) 還可以藉由在合適的溶劑中在合適的催化劑存在下在-10°C與100°C之間的溫度下用合適的氫源處理藉由化合物 (2) 之催化轉移氫化來製備。合適的系統的實例係在Pd/C、Pd(OAc)2
或Pd(OH)2
/C存在下在二氯甲烷/水或二氯甲烷/甲醇混合物中的四羥基二硼(J. Am. Chem. Soc
.
[美國化學會誌],2016
,138
, 6107-6110)或在Pd/C存在下在乙醇中的1,4-二氫-2,6-二甲基-3,5-吡啶二甲酸二乙酯(Tetrahedron Letters
[四面體通訊],2009
,50
, 1026)。
可替代地,化合物 (I-ii) 還可以藉由用由合適的先質原位生成的二醯亞胺在合適的溶劑中在-10°C與200°C之間的溫度下還原製備。用於生成二醯亞胺的合適的試劑的實例包括視需要在合適的鹼存在下經取代的芳基磺醯基醯肼,如2,4,6-三異丙基苯磺醯基醯肼。合適的鹼的實例包括三乙胺、二異丙基乙胺、碳酸鉀和碳酸鈉。合適的溶劑包括四氫呋喃、1,4-二㗁𠮿、乙酸乙酯、乙腈和二甲基甲醯胺。
如在反應流程 2
中所示,化合物 (2) 可以由化合物 (3) 和化合物 (4) 根據所述之鈴木方案(Suzuki Protocol)或赫克方案(Heck Protocol)來製備。當採用鈴木方案時,化合物 (4) 係有機硼化合物,如硼酸、硼酸酯或三氟硼酸鉀鹽。當採用赫克方案時,化合物 (4) 係苯乙烯。
鈴木方案
化合物 (2) 可以藉由在合適的鹼和合適的催化劑存在下在合適的溶劑中在10°C與150°C之間的溫度下用化合物 (4) 處理化合物 (3) 來製備。合適的鹼的實例係碳酸鉀、磷酸鉀、碳酸鈉、碳酸氫鈉和氟化鉀。合適的催化劑的實例係1,1′-雙(二苯基膦基)二茂鐵]二氯鈀(II)二氯甲烷錯合物 [PdCl2
(dppf).DCM]、四(三苯基膦)鈀(0) [Pd(PPh3
)4
]、以及由乙酸鈀(II) 和三苯基膦的混合物原位形成的催化系統。合適的溶劑的實例係水、1,4-二㗁𠮿、2-甲基四氫呋喃、四氫呋喃、乙腈和甲苯。許多化合物 (4) 係可商購的 [如4,4,5,5-四甲基-2-[(E)-2-(2-萘基)乙烯基]-1,3,2-二氧雜環戊硼烷(dioxaborolane)] 或者可以藉由已知之方法製得。在鈴木方案中具有特定效用的化合物 (3) 之實例係異丁醯酯 (3-i),其中G係異丁醯基。
技術人員將理解,鈴木方案的條件易於裂解酯基,使得反應流程2也可以描述以下反應,在該反應中起始材料 (3) 含有酯部分 [使得G為醯基],但產物 (2) 不含 [使得G為氫]。
赫克方案
化合物 (2) 可以藉由在合適的鹼和合適的催化劑存在下在10°C與150°C之間的溫度下用化合物 (4) 處理化合物 (3) 來製備。可以視需要包括額外的溶劑。合適的鹼的實例係三乙胺、𠰌啉、N
-甲基𠰌啉、二異丙基乙胺和吡啶。合適的催化劑的實例係四(三苯基膦)鈀(0) [Pd(PPh3
)4
]、由乙酸鈀(II) 和三苯基膦的混合物原位形成的催化系統、由三(二亞苄基丙酮)二鈀(0) 和三三級丁基鏻四氟硼酸鹽的混合物原位形成的催化系統以及由環鈀錯合物(palladacycle)預催化劑(如氯[(三三級丁基膦)-2-(2-胺基聯苯基)]鈀(II))原位形成的催化系統。視需要的額外的溶劑的實例係1,4-二㗁𠮿、四氫呋喃、乙腈和甲苯。許多化合物 (4) 係可商購的 [如2-乙烯基萘] 或者可以藉由已知之方法製得。在赫克方案中具有特定效用的化合物 (3) 之實例係異丁醯酯 (3-i),其中G係異丁醯基。
如在反應流程 3
中所示,可以由化合物 (5) 製備化合物 (3-i)。
化合物 (3-i) 可以藉由在合適的溶劑 [如二氯甲烷、乙腈或甲苯] 中在合適的鹼 [如三乙胺、二異丙基乙胺或吡啶] 存在下在-10°C與60°C之間的溫度下用異丁醯氯處理化合物 (5) 來製備。可以視需要包括催化劑 [如4-(二甲基胺基)吡啶]。
如在反應流程 4
中所示,化合物 (5) 可以由化合物 (6) 藉由在溶劑 [如乙腈、N,N
-二甲基甲醯胺或甲苯] 中在50°C與200°C之間的溫度下加熱化合物 (6) 與鹼(如1,8-二氮雜二環[5.4.0]十一碳-7-烯、六甲基二矽氮烷鈉或六甲基二矽氮烷鋰)來製備。可以使用常規加熱或微波加熱。
如在反應流程 5
中所示,化合物 (6) 可以由苯乙酸 (7) 製備。
關於反應流程 5
,肼 (8) 之實例係甲基肼,並且酮酯 (10) 之實例係丙酮酸乙酯。腙 (9) 之實例係(2E/Z)-2-(甲基亞肼基)丙酸乙酯,根據PCT專利申請WO 2016/008816中描述之方法製備。苯乙酸 (7) 之實例係(2-溴-6-氟-苯基)乙酸,其可以根據反應流程 10
來合成。苯乙酸 (7) 之另外的實例係(2-溴-3-氯-6-氟-苯基)乙酸,其可以根據反應流程 11
來合成。
本發明之某些化合物 (I-iii) 可以由化合物 (11)(如在反應流程 6
中所示)或化合物 (I-iv)(如在反應流程 12
中所示)製備。化合物 (I-iii) 係具有式 (I) 之化合物,其中W係-CH2
-CH2
-並且G係氫。
化合物 (I-iii) 可以藉由在溶劑 [如乙腈、N,N
-二甲基甲醯胺或甲苯] 中在50°C與200°C之間的溫度下加熱化合物 (11) 與鹼(如1,8-二氮雜二環[5.4.0]十一碳-7-烯、六甲基二矽氮烷鈉或六甲基二矽氮烷鋰)來製備。可以使用常規加熱或微波加熱。
如在以下反應流程 7
中所示,可以由化合物 (12) 製備化合物 (11)。
如在反應流程 8
中所示,可以由化合物 (13) 製備化合物 (12)。許多化合物 (13) 係可商購的 [如2-苯基乙酸甲酯和2-(2-氟苯基)乙酸甲酯]。
關於反應流程 8
,可以根據反應流程 9
來製備正膦 (15)。
關於反應流程 9
,合適的鹼的實例係氫化鈉、六甲基二矽氮烷鈉和三級丁醇鉀。化合物 (16) 係親電體,其中LG係脫離基 [如氯化物、溴化物、碘化物、甲苯磺酸酯或甲磺酸酯]。許多化合物 (16) 係可商購的 [如4-氯苄基溴或2-氯-5-氯甲基噻唑]。
關於反應流程 10
,可以如Lundgren等人JACS 2016
,138
, 13826-13829中所述之製備(2-溴-6-氟-苯基)乙酸乙基酯。
關於反應流程 11
,2-溴-1-氯-4-氟-苯係可商購的。
化合物 (I-iii) 可以藉由以下方式製備:在水和合適的溶劑 [如甲醇、乙醇或四氫呋喃] 的混合物中用金屬氫氧化物 [如氫氧化鈉、氫氧化鋰或氫氧化鉀] 處理化合物 (I-iv);或在0°C與100°C之間的溫度下在醇溶劑 [如甲醇或乙醇] 中用金屬碳酸鹽 [如碳酸鈉或碳酸鉀] 處理化合物 (I-iv)。化合物 (I-iv) 係具有式 (I) 之化合物,其中W係-CH2
-CH2
-並且G係C(O)R3
。
如在反應流程 13
中所示,化合物 (2) 可以由化合物 (14) 和化合物 (15) 根據所述之鈴木方案或赫克方案來製備。當採用鈴木方案時,化合物 (14) 係有機硼化合物,如硼酸、硼酸酯或三氟硼酸鉀鹽並且化合物 (15) 係鹵化物或擬鹵化物化合物,如氯化物、溴化物、碘化物或三氟甲磺酸鹽。當採用赫克方案時,化合物 (14) 係苯乙烯並且化合物 (15) 係鹵化物或擬鹵化物化合物,如氯化物、溴化物、碘化物或三氟甲磺酸鹽。
鈴木方案
化合物 (2) 可以藉由在合適的鹼和合適的催化劑存在下在合適的溶劑中在10°C與150°C之間的溫度下用化合物 (15) 處理化合物 (14) 來製備。合適的鹼的實例係碳酸鉀、磷酸鉀、碳酸鈉、碳酸氫鈉和氟化鉀。合適的催化劑的實例係1,1′-雙(二苯基膦基)二茂鐵]二氯鈀(II)二氯甲烷錯合物 [PdCl2
(dppf).DCM]、四(三苯基膦)鈀(0) [Pd(PPh3
)4
]、以及由乙酸鈀(II) 和三苯基膦的混合物原位形成的催化系統。合適的溶劑的實例係水、1,4-二㗁𠮿、2-甲基四氫呋喃、四氫呋喃、乙腈和甲苯。許多化合物 (15) 係可商購的或者可以藉由已知之方法製得。在鈴木方案中具有特定效用的化合物 (14) 之實例係異丁醯酯 (14-i),其中G係異丁醯基。
技術人員將理解,鈴木方案的條件易於裂解酯基,使得反應流程13也可以描述以下反應,在該反應中起始材料 (14) 含有酯部分 [使得G為醯基],但產物 (2) 不含 [使得G為氫]。
赫克方案
化合物 (2) 可以藉由在合適的鹼和合適的催化劑存在下在10°C與150°C之間的溫度下用化合物 (15) 處理化合物 (14) 來製備。可以視需要包括額外的溶劑。合適的鹼的實例係三乙胺、𠰌啉、N
-甲基𠰌啉、二異丙基乙胺和吡啶。合適的催化劑的實例係四(三苯基膦)鈀(0) [Pd(PPh3
)4
]、由乙酸鈀(II) 和三苯基膦的混合物原位形成的催化系統、由三(二亞苄基丙酮)二鈀(0) 和三三級丁基鏻四氟硼酸鹽的混合物原位形成的催化系統以及由環鈀錯合物預催化劑(如氯[(三三級丁基膦)-2-(2-胺基聯苯基)]鈀(II))原位形成的催化系統。視需要的額外的溶劑的實例係1,4-二㗁𠮿、四氫呋喃、乙腈和甲苯。許多化合物 (15) 係可商購的或者可以藉由已知之方法製得。在赫克方案中具有特定效用的化合物 (14) 之實例係異丁醯酯 (14-i),其中G係異丁醯基。
如在反應流程 14
中所示,可以由化合物 (3) 和化合物 (16) 製備化合物 (14-ii),其中J係有機硼物種,如硼酸酯。
化合物 (14-ii) 可以藉由在合適的鹼和合適的催化劑存在下在10°C與150°C之間的溫度下用化合物 (16) 處理化合物 (3) 來製備。可以視需要包括額外的溶劑。合適的鹼的實例係三乙胺、𠰌啉、N
-甲基𠰌啉、二異丙基乙胺和吡啶。合適的催化劑的實例係四(三苯基膦)鈀(0) [Pd(PPh3
)4
]、由乙酸鈀(II) 和三苯基膦的混合物原位形成的催化系統和由三(二亞苄基丙酮)二鈀(0) 和三三級丁基鏻四氟硼酸鹽的混合物原位形成的催化系統。視需要的額外的溶劑的實例係1,4-二㗁𠮿、四氫呋喃、乙腈和甲苯。許多化合物 (16) 係可商購的,如乙烯基硼酸MIDA酯或乙烯基硼酸酉品(pinacol)酯,或者可以藉由已知之方法製得。在赫克方案中具有特定效用的化合物 (3) 之實例係異丁醯酯 (3-i),其中G係異丁醯基。
如在以上反應流程 15
中所示,可以由化合物 (3) 製備化合物 (14-iii)(其中J係氫)。
化合物 (14-iii) 可以藉由視需要在合適的鹼存在下,在合適的催化劑存在下,在10°C與150°C之間的溫度下在合適的溶劑中用三丁基(乙烯基)錫烷處理化合物 (3) 來製備。視需要的鹼的實例係三乙胺、𠰌啉、N
-甲基𠰌啉、二異丙基乙胺和吡啶。合適的催化劑的實例係1,1′-雙(二苯基膦基)-二茂鐵]二氯鈀(II)二氯甲烷錯合物 [PdCl2
(dppf).DCM]、四(三苯基膦)鈀(0) [Pd(PPh3
)4
]、由乙酸鈀(II) 和三苯基膦的混合物原位形成的催化系統、由三(二亞苄基丙酮)二鈀(0) 和三三級丁基鏻四氟硼酸鹽的混合物原位形成的催化系統以及由環鈀錯合物預催化劑(如氯[(三三級丁基膦)-2-(2-胺基聯苯基)]鈀(II))原位形成的催化系統。合適的溶劑的實例係1,4-二㗁𠮿、四氫呋喃、乙腈和甲苯。具有特定效用的化合物 (3) 之實例係異丁醯酯 (3-i),其中G係異丁醯基。
如在反應流程 16
中所示,可以由化合物 (3) 藉由薗頭(Sonogashira)反應製備化合物 (18)。
化合物 (18) 可以藉由在合適的鹼和一種或多種合適的催化劑存在下在10°C與150°C之間的溫度下用化合物 (17) 處理化合物 (3) 來製備。視需要,可以添加額外的溶劑。合適的鹼的實例係三乙胺、𠰌啉、N
-甲基𠰌啉、二異丙胺、二異丙基乙胺和吡啶。合適的催化劑的實例係雙(三苯基膦)鈀(II)二氯化物 [Pd(PPh3
)Cl2
]、由乙酸鈀(II) 和三苯基膦的混合物原位形成的催化系統、由三(二亞苄基丙酮)二鈀(0) 和三三級丁基鏻四氟硼酸鹽的混合物原位形成的催化系統以及由環鈀錯合物預催化劑(如氯[(三三級丁基膦)-2-(2-胺基聯苯基)]鈀(II))原位形成的催化系統。視需要還可以添加銅催化劑,如碘化銅 (I)。合適的額外的溶劑的實例係1,4-二㗁𠮿、四氫呋喃、乙腈、甲苯和N,N-二甲基甲醯胺。具有特定效用的化合物 (3) 之實例係異丁醯酯 (3-i),其中G係異丁醯基。
技術人員將理解,薗頭反應的條件易於裂解酯基,使得反應流程16也可以描述以下反應,在該反應中起始材料 (3) 含有酯部分 [使得G為醯基],但產物 (18) 不含 [使得G為氫]。
如在反應流程 17
中所示,化合物 (19) 可以由化合物 (3) 和化合物 (20) 藉由鈴木反應製備,其中化合物 (20) 係合適的有機硼物種,如硼酸、硼酸酯或三氟硼酸鉀鹽。
化合物 (19) 可以藉由在合適的鹼和合適的催化劑存在下在合適的溶劑中在10°C與150°C之間的溫度下用化合物 (20) 處理化合物 (3) 來製備。合適的鹼的實例係碳酸鉀、磷酸鉀、碳酸鈉、碳酸氫鈉和氟化鉀。合適的催化劑的實例係1,1′-雙(二苯基膦基)二茂鐵]二氯鈀(II)二氯甲烷錯合物 [PdCl2
(dppf).DCM]、由三(二亞苄基丙酮)二鈀(0) 和三三級丁基鏻四氟硼酸鹽的混合物原位形成的催化系統、由三(二亞苄基丙酮)二鈀(0) 和三環己基膦的混合物原位形成的催化系統、由環鈀錯合物預催化劑(如氯[(三三級丁基膦)-2-(2-胺基聯苯基)]鈀(II))原位形成的催化系統、以及由環鈀錯合物預催化劑(如氯[(三環己基膦)-2-(2′-胺基聯苯基)]鈀(II))原位形成的催化系統。合適的溶劑的實例係水、1,4-二㗁𠮿、2-甲基四氫呋喃、四氫呋喃、乙腈和甲苯。一些化合物 (20) 係可商購的或者可以藉由已知之方法製得(參見例如Org.Process Res. Dev. [有機過程研究與發展], 2012, 16, 87-95中描述之方法)。在鈴木反應中具有特定效用的化合物 (3) 之實例係苄基醚 (3-ii),其中G係苄基。
化合物 (I9-ii) 可以藉由化合物 (19-i) 與氫氣在合適的溶劑 [如四氫呋喃、甲醇、乙醇、乙酸或乙酸乙酯] 中在合適的催化劑 [如Pd/C、Pd/CaCO3
、Rh/Al2
CO3
或海綿鎳] 存在下在-10°C與100°C之間的溫度下的催化氫化來製備。
如在反應流程 19
中所示,可以由化合物 (21) 製備本發明之某些化合物 (I-ii)。化合物 (I-ii) 係具有式 (I) 之化合物,其中W係-CH2
-CH2
-。
化合物 (I-ii) 可以藉由在合適的鹼和合適的催化劑存在下在合適的溶劑中在10°C與150°C之間的溫度下用化合物 (15) 處理化合物 (21)(其中 [B] 可為三烷基硼烷、烷基硼酸、烷基硼酸酯或烷基三氟硼酸鉀鹽)來製備。合適的鹼的實例係碳酸鉀、磷酸鉀、碳酸鈉、碳酸銫、碳酸氫鈉和氟化鉀。合適的催化劑的實例係1,1′-雙(二苯基膦基)二茂鐵]-二氯鈀(II)二氯甲烷錯合物 [PdCl2
(dppf).DCM]、[1,3-雙(2,6-二-3-戊基苯基)咪唑-2-亞基](3-氯吡啶基)二氯鈀(II) [Pd-PEPPSI™-IPent]、由環鈀錯合物預催化劑(如氯(2-二環己基膦基-2′,6′-二異丙氧基-1,1′-聯苯基)[2-(2′-胺基-1,1′-聯苯基)]鈀(II) [RuPhos-Pd-G2])原位形成的催化系統、[二環己基[2',4',6'-三(1-甲基乙基)[1,1'-聯苯基]-2-基]膦](甲烷磺酸基-κO)[2'-(甲基胺基-κN)[1,1'-聯苯基]-2-基-κC]鈀 [XPhos-Pd-G4]、以及 [(4-(N,N-二甲基胺基)苯基)二-三級丁基膦](甲烷磺酸基-κO)[2'-(甲基胺基-κN)[1,1'-聯苯基]-2-基-κC]鈀 [APhos-Pd-G4]。合適的溶劑的實例係水、1,4-二㗁𠮿、2-甲基四氫呋喃、四氫呋喃、乙腈和甲苯。許多化合物 (15) 係可商購的或者可以藉由已知之方法製得。在鈴木方案中具有特定效用的化合物 (21) 之實例係異丁醯酯 (21-i),其中G係異丁醯基。
技術人員將理解,鈴木方案的條件易於裂解酯基,使得反應流程19也可以描述以下反應,在該反應中起始材料 (21) 含有酯部分 [使得G為醯基],但產物 (I-ii) 不含 [使得G為氫]。
化合物 (21) 可以藉由在合適的溶劑中視需要添加合適的催化劑的情況下在0°C與100°C之間的溫度下使用合適的硼氫化試劑 (22) 進行烯烴 (14-iii) 之硼氫化來製備。硼氫化試劑的實例包括硼烷、二氯硼烷、二溴硼烷、4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷 [酉品硼烷]、1,3,2-苯并二氧雜戊硼烷 [兒茶酚硼烷]或9-硼基雙環[3.3.1]壬烷 [9-BBN]。合適的溶劑的實例包括四氫呋喃、2-甲基四氫呋喃、1,4-二㗁𠮿、2-甲氧基-2-甲基-丙烷 [MTBE) 和二乙醚。合適的催化劑的實例包括由雙(1,5-環辛二烯)二銥(I)二氯化物[[Ir(COD)Cl]2
]原位形成的催化系統、和4-二苯基磷烷基丁基(二苯基)磷烷[DPPB] [J. Am. Chem. Soc.
[美國化學會誌],2004
,126
, 9200-9201]。
在 [B] 係烷基硼酸酯時,這可以藉由在合適的溶劑如二氯甲烷 [DCM] 中在0°C與40°C之間的溫度下用甲基硼酸 [MeB(OH)2
] 和三氟乙酸處理而轉化為相應的硼酸 [Org.Lett
.
[有機快報],2019
,21
, 3048-3052]。在 [B] 係烷基硼酸或酯時,這可以藉由在合適的溶劑如甲醇或丙酮中在0°C與40°C之間的溫度下用氟氫化鉀處理而轉化為相應的烷基三氟硼酸鉀鹽。
根據本發明之化合物可以按未經修飾的形式用作除草劑,但它們通常以多種方式使用配製佐劑(如載體、溶劑和表面活性物質)被配製成組成物。該等配製物可以處於不同的實體形式,例如,處於以下形式:撒粉劑、凝膠、可濕性粉劑、水可分散性顆粒劑、水可分散性片劑、發泡顆粒、可乳化的濃縮物、微可乳化濃縮物、水包油乳劑、可流動油、水性分散體、油性分散體、懸乳劑、膠囊懸浮液、可乳化的顆粒劑、可溶性液體、水可溶性濃縮物(以水或水混溶性有機溶劑作為載體)、浸漬的聚合物膜或處於已知的其他形式,例如從Manual on Development and Use of FAO and WHO Specifications for Pesticides [關於殺有害生物劑的FAO和WHO標準的發展和使用的手冊],聯合國,第1版,二次修訂 (2010) 中已知的。此類配製物可以直接使用或者使用前進行稀釋。可以用例如水、液體肥料、微量營養素、生物有機體、油或溶劑來進行稀釋。
可以藉由例如將活性成分與配製佐劑混合來製備該等配製物以便獲得處於精細分散固體、顆粒、溶液、分散體或乳劑形式的組成物。該等活性成分還可以與其他佐劑(如精細分散固體、礦物油、植物或動物來源的油、改性的植物或動物來源的油、有機溶劑、水、表面活性物質或其組合)來一起配製。
該等活性成分還可以被包含於非常精細的微膠囊中。微膠囊在多孔載體中含有活性成分。這使活性成分能以受控的量釋放(例如,緩慢釋放)到環境中。微膠囊通常具有從0.1至500微米的直徑。它們包含的活性成分的量按重量計係膠囊重量的約從25%至95%。該等活性成分可以處於整體性的固體的形式、處於固體或液體分散體中的精細顆粒的形式或處於適合溶液的形式。包囊的膜可以包括例如天然的或合成的橡膠、纖維素、苯乙烯/丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚醯胺、聚脲、聚胺酯或化學改性的聚合物以及澱粉黃原酸酯、或熟悉該項技術者已知的其他聚合物。可替代地,可以形成非常精細的微膠囊,其中活性成分在基礎物質的固體基質中是以精細分散顆粒的形式被包含的,但該等微膠囊本身未經包裹。
適合於製備根據本發明之組成物的配製佐劑本身係已知的。作為液體載體可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、環己酮、酸酐、乙腈、乙醯苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、氯苯、環己烷、環己醇、乙酸烷基酯、二丙酮醇、1,2-二氯丙烷、二乙醇胺、對-二乙基苯、二甘醇、松脂酸二乙二醇酯、二甘醇丁基醚、二甘醇乙基醚、二甘醇甲醚、N,N
-二甲基甲醯胺、二甲基亞碸、1,4-二㗁𠮿、二丙二醇、二丙二醇甲基醚、雙丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯啶酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-薴烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁內酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸異戊基酯、乙酸異冰片基(isobornyl)酯、異辛烷、異佛耳酮、異丙苯、肉豆蔻酸異丙酯、乳酸、月桂胺、亞異丙基丙酮、甲氧基丙醇、甲基異戊基酮、甲基異丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、間二甲苯、正己烷、正辛胺、十八烷酸、辛胺乙酸酯、油酸、油胺、鄰二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸丙烯酯、丙二醇、丙二醇甲基醚、對-二甲苯、甲苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石蠟、礦物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、異丙醇以及更高分子量的醇,如戊醇、四氫呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、N
-甲基-2-吡咯啶酮等。
適合的固體載體係例如滑石、二氧化鈦、葉蠟石黏土、矽石、凹凸棒石黏土、矽藻土、石灰石、碳酸鈣、膨潤土、鈣蒙脫土、棉籽殼、小麥粉、大豆粉、浮石、木粉、經研磨的胡桃殼、木質素和類似的物質。
許多表面活性物質可以有利地用在固體和液體配製物兩者中,尤其是在使用前可被載體稀釋的那些配製物中。表面活性物質可為陰離子的、陽離子的、非離子的或聚合的並且它們可以用作乳化劑、濕潤劑或懸浮劑或用於其他目的。典型的表面活性劑包括,例如,烷基硫酸鹽,如二乙醇銨硫酸月桂基酯;烷芳基磺酸鹽,如十二烷基苯磺酸鈣;烷基酚/氧化烯加成產物,如壬基酚乙氧基化物;醇/烯烴氧化物加成產物,如十三烷醇乙氧基化物;皂,例如硬脂酸鈉;烷基萘磺酸鹽,如二丁基萘磺酸鈉;磺基琥珀酸鹽的二烷基酯,如二(2-乙基己基)磺基琥珀酸鈉;山梨糖醇酯,如山梨糖醇油酸酯;季胺類,如十二烷基三甲基氯化銨;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;環氧乙烷和環氧丙烷的嵌段共聚物;以及單烷基與二烷基磷酸酯的鹽;以及還有描述在例如McCutcheon's Detergents and Emulsifiers Annual [麥卡琴的洗滌劑和乳化劑年報], MC Publishing Corp. [MC出版公司], Ridgewood New Jersey [新澤西州裡奇伍德] (1981) 中的其他物質。
可以用於殺有害生物配製物的另外的佐劑包括結晶抑制劑、黏度調節劑、懸浮劑、染料、抗氧化劑、發泡劑、光吸收劑、混合助劑、消泡劑、錯合劑、中和或改變pH的物質和緩衝液、腐蝕抑制劑、香料、濕潤劑、吸收增強劑、微量營養素、塑化劑、助滑劑、潤滑劑、分散劑、增稠劑、防凍劑、殺微生物劑、以及液體和固體肥料。
根據本發明之組成物可以包括添加劑,該添加劑包括植物或動物來源的油、礦物油、此類油的烷基酯或此類油與油衍生物的混合物。在根據本發明之組成物中的油添加劑的量通常是基於該待施用的混合物的從0.01%到10%。例如,可以在噴霧混合物已經製備之後將油添加劑以所希望的濃度添加到噴霧罐中。較佳的油添加劑包括礦物油或植物來源的油,例如菜籽油、橄欖油或葵花籽油;乳化的植物油;植物來源的油的烷基酯,例如甲基衍生物;或動物來源的油,如魚油或牛脂。較佳的油添加劑包括C8
-C22
脂肪酸的烷基酯,尤其是C12
-C18
脂肪酸的甲基衍生物,例如月桂酸、棕櫚酸以及油酸的甲基酯(分別為月桂酸甲酯、棕櫚酸甲酯和油酸甲酯)。許多油衍生物從Compendium of Herbicide Adjuvants [除草劑佐劑綱要], 第10版, Southern Illinois University [南伊利諾大學], 2010中是已知的。
該除草組成物總體上包含按重量計從0.1%至99%、尤其是按重量計從0.1%至95%的具有式 (I) 之化合物和按重量計從1%至99.9%的配製佐劑,該配製佐劑較佳的是包括按重量計從0至25%的表面活性物質。該等本發明組成物總體上包括按重量計從0.1%至99%,尤其是按重量計從0.1%至95%的本發明之化合物以及按重量計從1%至99.9%的配製佐劑,該配製佐劑較佳的是包括按重量計從0至25%的表面活性物質。而商業產品可以較佳的是被配製為濃縮物,最終使用者將通常使用稀釋配製物。
施用率在寬範圍之內變化並且取決於土壤的性質、施用方法、作物植物、待控制的有害生物、主要氣候條件、以及受施用方法、施用時間和目標作物支配的其他因素。一般來講,可以將化合物以從1 l/ha至2000 l/ha、尤其是從10 l/ha到1000 l/ha的比率施用。
較佳的配製物可以具有以下組成(重量%):
可乳化的濃縮物:
活性成分: 1%至95%、較佳的是60%至90%
表面活性劑: 1%至30%、較佳的是5%至20%
液體載體: 1%至80%、較佳的是1%至35%
粉塵劑:
活性成分: 0.1%至10%、較佳的是0.1%至5%
固體載體: 99.9%至90%、較佳的是99.9%至99%
懸浮液濃縮物:
活性成分: 5%至75%、較佳的是10%至50%
水: 94%至24%、較佳的是88%至30%
表面活性劑: 1%至40%、較佳的是2%至30%
可濕性粉劑:
活性成分: 0.5%至90%、較佳的是1%至80%
表面活性劑: 0.5%至20%、較佳的是1%至15%
固體載體: 5%至95%、較佳的是15%至90%
顆粒劑:
活性成分: 0.1%至30%、較佳的是0.1%至15%
固體載體: 99.5%至70%、較佳的是97%至85%
本發明之組成物可以進一步包含至少一種另外的殺有害生物劑。例如,根據本發明之化合物也可以與其他除草劑或植物生長調節劑組合使用。在較佳的實施方式中,該另外的殺有害生物劑係除草劑和/或除草劑安全劑。
因此,具有式 (I) 之化合物可以與一種或多種其他除草劑組合使用以提供各種除草混合物。此類混合物的具體實例包括(其中「I」表示具有式 (I) 之化合物):- I + 乙草胺(acetochlor);I + 三氟羧草醚(acifluorfen)(包括三氟羧草醚-鈉);I + 苯草醚(aclonifen);I + 莠滅淨(ametryn);I + 胺唑草酮(amicarbazone);I + 氯胺基吡啶酸(aminopyralid);I + 殺草強(aminotriazole);I + 莠去津(atrazine);I + beflubutamid-M;I + benquitrione;I + 苄嘧磺隆(bensulfuron)(包括苄嘧磺隆-甲基);I + 噻草平(bentazone);I + 二環哌喃酮(bicyclopyrone);I + 雙丙胺膦(bilanafos);I + 雙草醚-鈉(bispyribac-sodium);I + bixlozone(bixlozone);I + 除草定(bromacil);I + 溴苯腈(bromoxynil);I + 丁草胺(butachlor);I + 氟丙嘧草酯(butafenacil);I + 唑酮草酯(carfentrazone)(包括唑酮草酯-乙基);氯酯磺草胺(cloransulam)(包括氯酯磺草胺-甲基);I + 氯嘧磺隆(chlorimuron)(包括氯嘧磺隆-乙基);I + 綠麥隆(chlorotoluron);I + 氯磺隆(chlorsulfuron);I + 環庚草醚(cinmethylin);I + 氯醯草膦(clacyfos);I + 烯草酮(clethodim);I + 炔草酸(clodinafop)(包括炔草酸-炔丙基);I + 異㗁草酮(clomazone);I + 二氯吡啶酸(clopyralid);I + 環吡拉尼(cyclopyranil);I + 環吡瑞莫(cyclopyrimorate);I + 環丙嘧磺隆(cyclosulfamuron);I + 氰氟草酯(cyhalofop)(包括氰氟草酯-丁基);I + 2,4-D(包括其膽鹼鹽和2-乙基己酯);I + 2,4-DB;I + 甜菜安(desmedipham);I + 麥草畏(dicamba)(包括其鋁;胺基丙基;雙-胺基丙基甲基;膽鹼;二氯丙;二甘醇胺;二甲胺;二甲基銨;鉀和鈉鹽);I + 雙氯磺草胺(diclosulam);I + 吡氟草胺(diflufenican);I + 氟吡草腙(diflufenzopyr);I + 二甲草胺(dimethachlor);I + 精二甲吩草胺(dimethenamid-P);I + 敵草快二溴化物(diquat dibromide);I + 敵草隆(diuron);I + epyrifenacil;I + 丁氟消草(ethalfluralin);I + 乙氧呋草黃(ethofumesate);I + 㗁唑禾草靈(fenoxaprop)(包括精㗁唑禾草靈-乙基);I + 異㗁苯碸(fenoxasulfone); I + fenquinotrione;I + 四唑醯草胺(fentrazamide);I + 啶嘧磺隆(flazasulfuron);I + 雙氟磺草胺(florasulam);I + 氯氟吡啶酯(florpyrauxifen)(包括氯氟吡啶酯-苄基);I + 吡氟禾草靈(fluazifop)(包括精吡氟禾草靈-丁基);I + 氟酮磺隆(flucarbazone)(包括氟酮磺隆-鈉);I + 氟噻草胺(flufenacet);I + 唑嘧磺草胺(flumetsulam);I + 丙炔氟草胺(flumioxazin);I + 氟草隆(fluometuron);I + 氟啶嘧磺隆(flupyrsulfuron)(包括氟啶嘧磺隆-甲基-鈉);I + 氟草煙(fluroxypyr)(包括氯氟吡氧乙酸(fluroxypyr-meptyl));I + 氟磺胺草醚(fomesafen);I + 甲醯胺磺隆(foramsulfuron);I + 草丁膦(glufosinate)(包括其銨鹽);I + 草甘膦(glyphosate)(包括其二銨;異丙基銨和鉀鹽);I + 氟氯吡啶酯(halauxifen)(包括氟氯吡啶酯-甲基);I + 吡氟氯禾靈(haloxyfop)(包括吡氟氯禾靈-甲基);I + 環𠯤酮(hexazinone);I + hydantocidin;I + 甲氧咪草煙(imazamox);I + 甲基咪草煙(imazapic);I + 滅草煙(imazapyr);I + 咪草煙(imazethapyr);I + 三𠯤茚草胺(indaziflam);I + 碘甲磺隆(iodosulfuron)(包括碘甲磺隆-甲基-鈉);I + iofensulfuron(包括I + iofensulfuron-鈉);I + 碘苯腈(ioxynil);I + 異丙隆(isoproturon);I + 異㗁唑草酮(isoxaflutole);I + lancotrione;I + MCPA;I + MCPB;I + 高二甲四氯丙酸(mecoprop-P);I + 甲基二磺隆(mesosulfuron)(包括I + 甲基二磺隆-甲基);I + 甲基磺草酮(mesotrione);I + 苯𠯤草酮(metamitron);I + 吡草胺(metazachlor);I + 異㗁噻草醚(methiozolin);I + 異丙甲草胺(metolachlor);I + 磺草唑胺(metosulam);I + 𠯤草酮(metribuzin);I + 甲磺隆(metsulfuron);I + 敵草胺(napropamide);I + 煙嘧磺隆(nicosulfuron);I + 達草滅(norflurazon);I + 㗁草酮(oxadiazon);I + 環氧嘧磺隆(oxasulfuron);I + 乙氧氟草醚(oxyfluorfen);I + 二氯化百草枯(paraquat dichloride);I + 二甲戊樂靈(pendimethalin);I + 五氟磺草胺(penoxsulam);I + 苯敵草(phenmedipham);I + 毒莠定(picloram);I + 唑啉草酯(pinoxaden);I + 丙草胺(pretilachlor);I + 氟嘧磺隆-甲基(primisulfuron-methyl);I + 撲草淨(prometryne);I + 敵稗(propanil);I + 喔草酯(propaquizafop);I + 丙𠯤嘧磺隆(propyrisulfuron),I + 戊炔草胺(propyzamide);I + 苄草丹(prosulfocarb);I + 氟磺隆(prosulfuron);I + 雙唑草腈(pyraclonil);I + 吡草醚(pyraflufen)(包括吡草醚-乙基);I + 磺醯草吡唑(pyrasulfotole);I + 噠草特(pyridate);I + 環酯草醚(pyriftalid);I + pyrimisulfan,I + 吡咯磺隆(pyroxasulfone);I + 啶磺草胺(pyroxsulam);I + 二氯喹啉酸(quinclorac);I + 氯甲喹啉酸(quinmerac);I + 喹禾靈(quizalofop)(包括精喹禾靈-乙基和喹禾糠酯(quizalofop-P-tefuryl));I + 碸嘧磺隆(rimsulfuron);I + 嘧啶肟草醚(saflufenacil);I + 烯禾啶(sethoxydim);I + 西瑪津(simazine);I + S-異丙甲草胺(S-metalochlor);I + 甲磺草胺(sulfentrazone);I + 磺醯磺隆(sulfosulfuron);I + 特丁噻草隆(tebuthiuron);I + 特呋三酮(tefuryltrione);I + 環磺酮(tembotrione);I + 特丁津(terbuthylazine);I + 特丁淨(terbutryn);I + tetflupyrolimet;I + 噻酮磺隆(thiencarbazone);I + 噻吩磺隆(thifensulfuron);I + 地芬納噻(tiafenacil);I + 托比利特(tolpyralate);I + 苯吡唑草酮(topramezone);I + 三甲苯草酮;I + 氟酮磺草胺(triafamone);I + 野麥畏(triallate);I + 醚苯磺隆(triasulfuron);I + 苯磺隆(tribenuron)(包括苯磺隆-甲基);I + 綠草定(triclopyr);I + 三氟啶磺隆(trifloxysulfuron)(包括三氟啶磺隆-鈉);I + 三氣草嗦(trifludimoxazin);I + 氟樂靈(trifluralin);I + 氟胺磺隆(triflusulfuron);I + 3-(2-氯-4-氟-5-(3-甲基-2,6-二側氧基-4-三氟甲基-3,6-二氫嘧啶-1(2H)-基)苯基)-5-甲基-4,5-二氫異㗁唑-5-甲酸乙酯;I + 4-羥基-1-甲氧基-5-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啶-2-酮;I + 4-羥基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啶-2-酮;I + 5-乙氧基-4-羥基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啶-2-酮;I + 4-羥基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啶-2-酮;I + 4-羥基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-基]咪唑啶-2-酮;I + (4R)1-(5-三級丁基異㗁唑-3-基)-4-乙氧基-5-羥基-3-甲基-咪唑啶-2-酮;I + 3-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]雙環[3.2.1]辛烷-2,4-二酮;I + 2-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]-5-甲基-環己烷-1,3-二酮;I + 2-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]環己烷-1,3-二酮;I + 2-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]-5,5-二甲基-環己烷-1,3-二酮;I + 6-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]-2,2,4,4-四甲基-環己烷-1,3,5-三酮;I + 2-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]-5-乙基-環己烷-1,3-二酮;I + 2-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]-4,4,6,6-四甲基-環己烷-1,3-二酮;I + 2-[6-環丙基-2-(3,4-二甲氧基苯基)-3-側氧基-嗒𠯤-4-羰基]-5-甲基-環己烷-1,3-二酮;I + 3-[6-環丙基-2-(3,4-二甲氧基苯基)-3-側氧基-嗒𠯤-4-羰基]雙環[3.2.1]辛烷-2,4-二酮;I + 2-[6-環丙基-2-(3,4-二甲氧基苯基)-3-側氧基-嗒𠯤-4-羰基]-5,5-二甲基-環己烷-1,3-二酮;I + 6-[6-環丙基-2-(3,4-二甲氧基苯基)-3-側氧基-嗒𠯤-4-羰基]-2,2,4,4-四甲基-環己烷-1,3,5-三酮;I + 2-[6-環丙基-2-(3,4-二甲氧基苯基)-3-側氧基-嗒𠯤-4-羰基]環己烷-1,3-二酮;I + 4-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]-2,2,6,6-四甲基-四氫哌喃-3,5-二酮;I + 4-[6-環丙基-2-(3,4-二甲氧基苯基)-3-側氧基-嗒𠯤-4-羰基]-2,2,6,6-四甲基-四氫哌喃-3,5-二酮;I + 4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸(包括其農用化學上可接受的酯,例如,4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸甲酯、4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸丙-2-炔酯和4-胺基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸氰基甲酯);I + 3-乙基氫硫基-N-(1,3,4-㗁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲醯胺;I + 3-(異丙基氫硫基甲基)-N-(5-甲基-1,3,4-㗁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲醯胺;I + 3-(異丙基磺醯基甲基)-N-(5-甲基-1,3,4-㗁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲醯胺;I + 3-(乙基磺醯基甲基)-N-(5-甲基-1,3,4-㗁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲醯胺;I + 2-[[3-[[3-氯-5-氟-6-[3-甲基-2,6-二側氧基-4-(三氟甲基)嘧啶-1-基]-2-吡啶基]氧基]乙酸乙酯;I + 6-氯-4-(2,7-二甲基-1-萘基)-5-羥基-2-甲基-嗒𠯤-3-酮;I + 1-[2-氯-6-(5-氯嘧啶-2-基)氧基-苯基]-4,4,4-三氟-丁-1-酮以及I + 5-[2-氯-6-(5-氯嘧啶-2-基)氧基-苯基]-3-(二氟甲基)異㗁唑。具有式 (I) 之化合物的混合配伍物還可以呈酯或鹽的形式,如例如在The Pesticide Manual [殺有害生物劑手冊], 第十四版, British Crop Protection Council [英國作物保護委員會], 2006中所提到的。
具有式 (I) 之化合物還可以在與其他農用化學品(如殺真菌劑、殺線蟲劑或殺昆蟲劑)的混合物中使用,該等農用化學品的實例在殺有害生物劑手冊中給出。
具有式 (I) 之化合物與混合配伍物的混合比較佳的是從1 : 100至1000 : 1。
該等混合物可以有利地用於以上提到的配製物中(在這種情況下「活性成分」涉及具有式 (I) 之化合物與混合配伍物的對應混合物)。
本發明之具有式 (I) 之化合物也可以與除草劑安全劑組合。較佳的組合(其中「I」表示具有式 (I) 之化合物)包括:- I + 解草𠯤(benoxacor),I + 解草酯(cloquintocet)(包括解草喹(cloquintocet-mexyl));I + 環丙磺醯胺(cyprosulfamide);I + 二氯丙烯胺(dichlormid);I + 解草唑(fenchlorazole)(包括解草唑-乙基);I + 解草啶(fenclorim);I + 氟草肟(fluxofenim);I + 解草㗁唑(furilazole) I + 雙苯㗁唑酸(isoxadifen)(包括雙苯㗁唑酸-乙基);I + 吡唑解草酸(mefenpyr)(包括吡唑解草酸-二乙基);I + metcamifen;I + N-(2-甲氧基苯甲醯基)-4-[(甲基胺基羰基)胺基]苯磺醯胺和I + 解草腈(oxabetrinil)。
特別較佳的是具有式 (I) 之化合物與環丙磺醯胺、雙苯㗁唑酸(包括雙苯㗁唑酸-乙基)、解草酯(包括解草喹)和/或N-(2-甲氧基苯甲醯基)-4-[(甲基-胺基羰基)胺基]苯磺醯胺的混合物。
具有式 (I) 之化合物的安全劑還可以處於酯或鹽的形式,例如像在殺有害生物劑手冊,第14版(BCPC),2006中所提到的。對解毒喹的提及還適用於鋰、鈉、鉀、鈣、鎂、鋁、鐵、銨、季銨、鋶或其鏻鹽(如在WO 02/34048中揭露的),並且對解草唑乙酯的提及還適用於解草唑等。
較佳的是,具有式 (I) 之化合物與安全劑的混合比係從100 : 1至1 : 10,尤其是從20 : 1至1 : 1。
該等混合物可有利地用於以上提到的配製物中(在這種情況下「活性成分」涉及具有式 (I) 之化合物與安全劑的對應混合物)。
本發明之具有式 (I) 之化合物作為除草劑係有用的。因此,本發明還包括用於控制不想要的植物之方法,包括向所述植物或包含它們的場所施用有效量的本發明化合物或含有所述化合物的除草組成物。「控制」意指殺死、減少或延遲生長或防止或減少發芽。通常有待控制的植物係不想要的植物(雜草)。「場所」意指植物正生長或將生長的區域。
具有式 (I) 之化合物的施用率可以在寬範圍之內變化並且取決於土壤的性質、施用方法(出苗前;出苗後;施用至種子壟溝;免耕施用等)、作物植物、一種或多種有待控制的雜草、主要氣候條件、以及受施用方法、施用時間以及目標作物支配的其他因素。根據本發明之具有式 (I) 之化合物通常以從10 g/ha至2000 g/ha,尤其是從50 g/ha到1000 g/ha的比率施用。
通常藉由噴灑該組成物進行施用,典型地是藉由用於大面積的裝在拖拉機上的噴灑機,但是還可以使用其他方法如撒粉(針對粉末)、滴加或浸濕。
可以使用根據本發明之組成物的有用植物包括作物如穀物,例如大麥和小麥、棉花、油菜籽油菜、向日葵、玉米、稻、大豆、甜菜、甘蔗以及草皮。
作物植物還可以包括樹,如果樹、棕櫚樹、椰子樹或其他堅果。還包括藤本植物(如葡萄)、灌木果樹、果實植物和蔬菜。
作物應被理解為還包括藉由常規的育種方法或藉由基因工程已經賦予對除草劑或多種類別的除草劑(例如ALS-抑制劑、GS-抑制劑、EPSPS-抑制劑、PPO-抑制劑、ACC酶-抑制劑以及HPPD-抑制劑)的耐受性的那些作物。藉由常規育種方法已經賦予其對咪唑啉酮(例如,甲氧咪草煙)的耐受性的作物的實例係Clearfield®夏季油菜(卡諾拉(canola))。藉由基因工程方法而賦予對除草劑的耐受性的作物的實例包括例如草甘膦和草丁膦抗性的玉米品種,該玉米品種在RoundupReady®和LibertyLink®商標名下是可商購的。
作物還應被理解為藉由基因工程方法已經賦予其對有害昆蟲的抗性的那些作物,例如Bt玉米(對歐洲玉米螟有抗性)、Bt棉花(對棉鈴象鼻蟲有抗性)以及還有Bt馬鈴薯(對科羅拉多甲蟲有抗性)。Bt玉米的實例係NK®的Bt 176玉米雜交體(先正達種子公司(Syngenta Seeds))。Bt毒素係由蘇雲金芽孢桿菌土壤細菌天然形成的蛋白質。毒素或能夠合成此類毒素的轉基因植物的實例被描述在EP-A-451 878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073和EP-A-427 529中。包含一個或多個編碼殺昆蟲劑抗性和表現一種或多種毒素的基因的轉基因植物的實例係KnockOut®(玉米)、Yield Gard®(玉米)、NuCOTIN33B®(棉花)、Bollgard®(棉花)、NewLeaf®(馬鈴薯)、NatureGard®以及Protexcta®。植物作物或其種子材料均可為抗除草劑的並且同時係抗昆蟲攝食的(「疊加的」轉基因結果)。例如,種子可以在具有表現殺昆蟲的Cry3蛋白的能力的同時係耐草甘膦的。
作物還應被理解為包括藉由常規育種方法或基因工程獲得並且含有所謂輸出性狀(例如改進的儲存穩定性、更高的營養價值以及改進的香味)的那些作物。
其他有用的植物包括例如在高爾夫球場、草地、公園以及路旁的或者商業上種植用於草地的草皮草,以及觀賞植物,如花卉或灌木。
本發明之具有式 (I) 之化合物和組成物通常可以用於控制多種單子葉和雙子葉雜草物種。典型地可以被控制的單子葉物種的實例包括大穗看麥娘(Alopecurus myosuroides
)、野燕麥(Avena fatua
)、車前臂形草(Brachiaria plantaginea
)、旱雀麥(Bromus tectorum
)、油莎草(Cyperus esculentus
)、馬唐(Digitaria sanguinalis
)、稗草(Echinochloa crus-galli
)、多年生黑麥草(Lolium perenn
)、多花黑麥草(Lolium multiflorum
)、黍稷(Panicum miliaceum
)、一年生早熟禾(Poa annua
)、狗尾草(Setaria viridis
)、大狗尾草(Setaria faberi
)和兩色蜀黍(Sorghum bicolor
)。可以被控制的雙子葉物種的實例包括:苘麻(Abutilon theophrasti
)、反枝莧(Amaranthus retroflexus
)、鬼針草、藜草(Chenopodium album
)、白苞猩猩草、豬殃殃、牽牛花、地膚(Kochia scoparia
)、卷莖蓼(Polygonum convolvulus
)、刺金午時花(Sida spinosa
)、新疆野生油菜(Sinapis arvensis
)、龍葵、繁縷(Stellaria media
)、波斯婆婆納(Veronica persica
)和蒼耳(Xanthium strumarium
)。雜草還可以包括可被認為係作物植物但是在作物區外生長的植物(「逃逸者(escapes)」),或從先前栽培的不同作物留下的種子生長的植物(「志願者(volunteers)」)。此類志願者或逃逸者可為對某些其他除草劑耐受的。
現在藉由舉例更詳細地說明本發明之不同方面和實施方式。應當理解的是,在不偏離本發明範圍的情況下,可以對細節做出修改。
製備實施例
實施例
1 2-
甲基丙酸
[5-[3-
氯
-6-
氟
-2-[2-(2-
甲基
-6-
喹啉基
)
乙基
]
苯基
]-1,3-
二甲基
-6-
側氧基
-
嗒
𠯤
-4-
基
]
酯
(A-3.034)
之製備
1.1 3-
烯丙基
-2-
溴
-1-
氯
-4-
氟
-
苯
將二異丙基胺基鋰的溶液(在四氫呋喃中2 M,3.6 ml,7.2 mmol)在N2
下冷卻至-78°C。在-78°C下,逐滴地添加2-溴-1-氯-4-氟-苯(1.0 g,4.8 mmol)在四氫呋喃中的溶液。將混合物在用烯丙基溴(0.3 ml,5.7 mmol)處理之前在同一溫度下攪拌45分鐘。將反應在-78°C下繼續進行2 h,然後升溫至室溫。將反應用飽和NH4
Cl(水性)淬滅並且用乙酸乙酯萃取。將有機物分離並保留,然後將其用鹽水洗滌。將有機物經硫酸鈉乾燥並在減壓下濃縮,以給出呈油狀物的3-烯丙基-2-溴-1-氯-4-氟-苯(1.2 g,100%)。
1
H NMR (400 MHz, CDCl3
) δH
: 7.34-7.30 (m, 1H), 7.01-6.96 (m, 1H), 5.94-5.83 (m, 1H), 5.10-5.00 (m, 2H), 3.64-3.58 (m, 2H)。
1.2 2-(2-
溴
-3-
氯
-6-
氟
-
苯基
)
乙酸
將3-烯丙基-2-溴-1-氯-4-氟-苯(15.0 g,60.1 mmol)於二氯甲烷(200 mL)中的溶液在2頸燒瓶中冷卻至-78°C。將一側頸連接到包含KI的水溶液的收集器上。將臭氧鼓泡通過該溶液,直至起始材料被完全消耗(5小時)。將空氣鼓泡通過該溶液持續10分鐘,以除去過量的臭氧。添加二甲基硫醚(44 ml,601 mmol),並將混合物升溫至室溫。將該反應在室溫下繼續16 h。
將混合物用鹽水(2 × 100 mL)洗滌,並保留有機層。將有機物經Na2
SO4
乾燥、過濾並在減壓下濃縮,以給出粗的2-(2-溴-3-氯-6-氟-苯基)乙醛(15.3 g),將其不經進一步純化用於下一步驟。
將粗的2-(2-溴-3-氯-6-氟-苯基)乙醛(15.3 g,60.8 mmol)溶於三級丁醇(92 mL)和水(46 mL)的混合物中,然後冷卻至0°C。添加2-甲基丁-2-烯(64.5 mL,608 mmol)、磷酸二氫鈉(34.6 g,243 mmol)和亞氯酸鈉(16.5 g,163 mmol)。將混合物攪拌2 h,然後用鹽水(150 mL)和2 M鹽酸(150 mL)稀釋。將混合物用乙酸乙酯(3 × 100 mL)萃取。將合併的有機萃取物用飽和焦亞硫酸鈉水溶液(100 mL)洗滌,然後經Na2
SO4
乾燥、過濾並在減壓下濃縮以提供淡黃色固體。將粗固體溶解水(100 mL)和2.0 M NaOH(30 mL)的混合物中。將水溶液用乙酸乙酯(100 mL)洗滌並丟棄有機物。藉由添加濃鹽酸(20 mL)將水層酸化,導致形成白色懸浮液。將混合物用乙酸乙酯(3 × 200 mL)萃取。將合併的有機物用鹽水洗滌、經Na2
SO4
乾燥、過濾並蒸發,以提供呈白色固體的2-(2-溴-3-氯-6-氟-苯基)乙酸(8.0 g,49%)。
1
H NMR (400 MHz, DMSO-d6
) δH
: 12.79 (br.s, 1H), 7.67-7.59 (m, 1H), 7.39-7.31 (m, 1H), 3.82 (s, 2H)。
1.3 2-(2-
溴
-3-
氯
-6-
氟
-
苯基
)-N
-
甲基
-
乙醯肼
向0°C下的2-(2-溴-3-氯-6-氟-苯基)乙酸(2.0 g,7.5 mmol)在二氯甲烷(20 ml)中的攪拌溶液中添加N
-(3-二甲基胺基丙基)-N
′-乙基碳二亞胺鹽酸鹽 [EDC.HCl](1.4 g,9.0 mmol),接著逐滴地添加甲基肼(0.4 ml,7.5 mmol)。將反應混合物的溫度維持在0°C持續3 h。然後將反應用水淬滅並萃取至二氯甲烷中。將有機物分離、用鹽水洗滌並經Na2
SO4
乾燥。在減壓下濃縮給出粗的2-(2-溴-3-氯-6-氟-苯基)-N
-甲基-乙醯肼(1.8 g,81%),將其不經進一步純化用於下一步驟。
1
H NMR (400 MHz, DMSO-d6) δH
: 7.59 (dd, J=8.9和5.4, 1H), 7.30 (t, J=8.9, 1H), 4.91 (s, 2H), 4.10 (br. s, 2H), 3.02 (s, 3H)。
1.4 2-{[2-(2-
溴
-3-
氯
-6-
氟
-
苯基
)-
乙醯基
]-
甲基
-
亞肼基
}-
丙酸乙基酯
向2-(2-溴-3-氯-6-氟-苯基)-N
-甲基-乙醯肼(1.8 g,6.09 mmol)在乙醇(5 ml)中的攪拌溶液中逐滴地添加丙酮酸乙酯(0.7 ml,6.7 mmol)。將反應在80°C下加熱4 h。然後將反應混合物冷卻至室溫,並在減壓下蒸發。將殘餘物藉由矽膠管柱層析法(洗提液:乙酸乙酯/己烷梯度)純化,以給出呈灰白色固體的所希望的化合物2-{[2-(2-溴-3-氯-6-氟-苯基)-乙醯基]-甲基-亞肼基}-丙酸乙基酯(1.8 g,75%)。
1
H NMR (400 MHz, CDCl3
) δH
: 7.40-7.35 (m, 1H), 7.04-6.98 (m, 1H), 4.32 (q, J=7.1, 2H), 4.24 (s, 2H), 3.41 (s, 3H), 2.32 (s, 3H), 1.36 (t, J=7.1, 3H)。
1.5 4-(2-
溴
-3-
氯
-6-
氟
-
苯基
)-5-
羥基
-2,6-
二甲基
-
嗒
𠯤
-3-
酮
將2-{[2-(2-溴-3-氯-6-氟-苯基)-乙醯基]-甲基-亞肼基}-丙酸乙基酯(500 mg,1.27 mmol)溶解於乙腈(2.5 ml)中並用1,8-二氮雜二環[5.4.0]十一碳-7-烯 [DBU](0.47 ml,3.2 mmol)處理。使用微波輻射將混合物加熱至125°C持續1 h。然後將反應混合物在減壓下蒸發。將殘餘物溶解於水中並用2 N鹽酸酸化至pH 1。將混合物用DCM萃取,將有機物分離並用鹽水溶液洗滌。將有機溶液經Na2
SO4
乾燥並在減壓下濃縮以給出粗產物。將該粗產物藉由矽膠管柱層析法(洗提液:乙酸乙酯/己烷梯度)純化以給出呈灰白色固體的4-(2-溴-3-氯-6-氟-苯基)-5-羥基-2,6-二甲基-嗒𠯤-3-酮(340 mg,77.1%)。
1
H NMR (400 MHz, DMSO-d6) δH
: 11.01 (s, 1H), 7.77-7.73 (m, 1H), 7.39 (t, J=8.7, 1H), 3.58 (s, 3H), 2.24 (s, 3H)。
1.6 2-
甲基丙酸
[5-(2-
溴
-3-
氯
-6-
氟
-
苯基
)-1,3-
二甲基
-6-
側氧基
-
嗒
𠯤
-4-
基
]
酯
向室溫下的4-(2-溴-3-氯-6-氟-苯基)-5-羥基-2,6-二甲基-嗒𠯤-3-酮(1.4 g,4.02 mmol)在二氯甲烷(32 ml)中的攪拌溶液中添加三乙胺(1.1 ml,8.06 mmol)、4-(二甲基胺基)吡啶 [DMAP](49 mg,0.40 mmol)和異丁醯氯(0.6 ml,4.83 mmol)。
一旦判斷完成,將反應用二氯甲烷和水稀釋。將有機層分離、經Na2
SO4
乾燥並在減壓下濃縮以給出粗產物。將該粗產物藉由矽膠管柱層析法(洗提液:乙酸乙酯/己烷梯度)純化以給出2-甲基丙酸[5-(2-溴-3-氯-6-氟-苯基)-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(1.47 g,87%)。
1
H NMR (400 MHz, CDCl3
) δH
: 7.51-7.47 (m, 1H), 7.10-7.05 (m, 1H), 3.82 (s, 3H), 2.60-2.55 (m, 1H), 2.25 (s, 3H), 1.02-0.98 (m, 6H)。
1.7 2-
甲基
-6-[(E)-2-(4,4,5,5-
四甲基
-1,3,2-
二氧雜環戊硼烷
-2-
基
)
乙烯基
]
喹啉
將4,4,5,5-四甲基-2-乙烯基-1,3,2-二氧雜環戊硼烷(0.73 mL,4.32 mmol)和N,N-二異丙基乙胺(1.25 mL,7.20 mmol)添加到6-溴-2-甲基-喹啉(800 mg,3.6 mmol)和氯[(三三級丁基膦)-2-(2-胺基聯苯基)]鈀(II)(92 mg,0.18 mmol)在甲苯(14 mL)中的攪拌溶液中。將反應混合物在氮氣下加熱至95°C持續4 h。
完成後將反應混合物冷卻至室溫,然後通過Celite®過濾(用DCM洗提)。將濾液在真空中濃縮,然後藉由快速管柱層析法(二氧化矽,洗提液:乙酸乙酯/異己烷梯度)純化以給出2-甲基-6-[(E)-2-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)乙烯基]喹啉(886 mg,83%產率)。
1
H NMR (400 MHz, 溶劑) δ ppm 1.34 (s, 12 H) 2.74 (s, 3 H) 6.29 (d, J=18.46 Hz, 1 H) 7.26 - 7.29 (m, 1 H) 7.55 (d, J=18.4 Hz, 1 H) 7.77 (d, J=1.47 Hz, 1 H) 7.85 - 7.92 (m, 1 H) 7.94 - 7.99 (m, 1 H) 8.02 (d, J=8.4 Hz, 1 H)。
1.8 2-
甲基丙酸
[5-[3-
氯
-6-
氟
-2-[(E)-2-(2-
甲基
-6-
喹啉基
)
乙烯基
]
苯基
]-1,3-
二甲基
-6-
側氧基
-
嗒
𠯤
-4-
基
]
酯
(A-4.034)
將2-甲基丙酸[5-(2-溴-3-氯-6-氟-苯基)-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(1.03 g,2.47 mmol)、Cs2
CO3
(2.43 g,7.40 mmol)、2-甲基-6-[(E)-2-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)乙烯基]喹啉(0.874 g,2.96 mmol)和Pd(dppf)Cl2
.DCM(0.101 g,0.123 mmol)在1,4-二㗁𠮿(21 mL)和水(6 mL)中的攪拌溶液在回流下加熱。
16 h後,將反應混合物在真空中濃縮以除去大部分的該二㗁𠮿,然後用水和EtOAc稀釋。分離有機層並且用多個部分的EtOAc(2 X)萃取水相。然後用2 M HCl(水性)將水相的pH調節至pH 2,然後用另外部分的EtOAc萃取。
將粗產物藉由快速管柱層析法(二氧化矽,洗提液:乙酸乙酯/異己烷梯度)純化以給出2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(2-甲基-6-喹啉基)乙烯基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(86 mg,7%產率,A-4.034
)和4-[3-氯-6-氟-2-[(E)-2-(2-甲基-6-喹啉基)乙烯基]苯基]-5-羥基-2,6-二甲基-嗒𠯤-3-酮(51 mg,5%產率,A
-2.034
)。
1
H NMR (400 MHz, CDCl3
) δ ppm 1.11 (app t, J=7.1 Hz, 6 H) 2.23 (s, 3 H) 2.63 - 2.71 (m, 1 H) 2.74 (s, 3 H) 3.69 (s, 3 H) 6.81 (d, J=16.4 Hz, 1 H) 7.04 (t, J=8.7 Hz, 1 H) 7.15 (d, J=16.5 Hz, 1 H) 7.27 (s, 1 H) 7.45 (dd, J=8.9, 5.07 Hz, 1 H) 7.63 (d, J=1.7 Hz, 1 H) 7.75 - 7.81 (m, 1 H) 7.94 (d, J=8.8 Hz, 1 H) 8.01 (d, J=8.3 Hz, 1 H)。
1
H NMR (400 MHz, CDCl3
) δ ppm 2.24 (s, 3 H) 2.66 (s, 3 H) 3.66 (s, 3 H) 6.72 (d, J=16.4 Hz, 1 H) 6.93 - 7.07 (m, 2 H) 7.26 (s, 1 H) 7.38 (dd, J=8.9, 5.14 Hz, 1 H) 7.55 (d, J=1.7 Hz, 1 H) 7.66 (dd, J=8.8, 2.0 Hz, 1 H) 7.84 (d, J=8.8 Hz, 1 H) 7.99 (d, J=8.4 Hz, 1 H)
1.9 2-
甲基丙酸
[5-[3-
氯
-6-
氟
-2-[2-(2-
甲基
-6-
喹啉基
)
乙基
]
苯基
]-1,3-
二甲基
-6-
側氧基
-
嗒
𠯤
-4-
基
]
酯
(A-3.034)
使2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(2-甲基-6-喹啉基)乙烯基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(56 mg,0.12 mmol,4.034
)在3巴H2
下在四氫呋喃(0.3 mL)中在5% Pd/C催化劑(24 mg)上經受催化氫化。
完成後,將反應混合物通過Celite®墊過濾,用DCM洗提。將濾液在真空中濃縮以得到粗殘餘物。
將殘餘物吸附到二氧化矽上並藉由快速管柱層析法(二氧化矽,洗提液:乙酸乙酯/異己烷)純化以給出2-甲基丙酸[5-[3-氯-6-氟-2-[2-(2-甲基-6-喹啉基)乙基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(15 mg,27%產率,A-3.034
)以及進一步還原的產物的混合物(將其藉由質量定向的逆相製備型HPLC進一步純化以給出2-甲基丙酸[5-[3-氯-6-氟-2-[2-(2-甲基-1,2,3,4-四氫喹啉-6-基)乙基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(6 mg,11%產率,A-3.030
))。
1
H NMR (400 MHz, CDCl3
) δ ppm 0.97 (dd, J=7.0, 4.4 Hz, 6 H) 2.24 (s, 3 H) 2.47 - 2.57 (m, 1 H) 2.73 (s, 3 H) 2.79 - 3.09 (m, 4 H) 3.84 (s, 3 H) 7.00 (t, J=8.6 Hz, 1 H) 7.25 (d, J=8.3 Hz, 1 H) 7.49 (app d, J=1.1 Hz, 3 H) 7.90 (d, J=8.4 Hz, 1 H) 7.96 (d, J=8.3 Hz, 1 H)。
1
H NMR (400 MHz, CDCl3
) δ ppm 0.96 (dd, J=7.03, 2.02 Hz, 6 H) 1.25 (d, J=6.24 Hz, 3 H) 1.58 - 1.69 (m, 1 H) 1.90 - 1.98 (m, 1 H) 2.24 (s, 3 H) 2.54 (dt, J=13.94, 6.97 Hz, 1 H) 2.63 - 2.84 (m, 6 H) 3.39 (td, J=6.51, 3.12 Hz, 1 H) 3.83 (s, 3 H) 6.52 (br d, J=6.48 Hz, 1 H) 6.72 - 6.79 (m, 2 H) 6.96 (t, J=8.62 Hz, 1 H) 7.40 (dd, J=8.80, 5.14 Hz, 1 H)。
2.1 5-
苄氧基
-4-(2-
溴
-3-
氯
-6-
氟
-
苯基
)-2,6-
二甲基
-
嗒
𠯤
-3-
酮
將苄基溴(0.19 mL,1.58 mmol)添加到4-(2-溴-3-氯-6-氟-苯基)-5-羥基-2,6-二甲基-嗒𠯤-3-酮(500 mg,1.44 mmol)和K2
CO3
(0.22 g,1.58 mmol)在丙酮(2.9 mL)中的攪拌懸浮液中並且將混合物在回流下加熱2小時。
完成後將反應混合物冷卻至室溫,然後過濾(用丙酮洗提)。將濾液在真空中濃縮,然後藉由快速管柱層析法(二氧化矽,洗提液:乙酸乙酯/異己烷梯度)純化以給出5-苄氧基-4-(2-溴-3-氯-6-氟-苯基)-2,6-二甲基-嗒𠯤-3-酮(560 mg,89%產率)。
1
H NMR (400 MHz, CDCl3
) δ ppm 2.29 (s, 3 H) 3.77 (s, 3 H) 4.59 - 4.76 (m, 2 H) 7.09 (dd, J=8.93, 7.95 Hz, 1 H) 7.13 - 7.20 (m, 2 H) 7.29 - 7.36 (m, 3 H) 7.52 (dd, J=8.93, 5.38 Hz, 1 H)。
2.2 2-[(E)-2-[2-(5- 苄氧基 -2,6- 二甲基 -3- 側氧基 - 嗒 𠯤 -4- 基 )-6- 氯 -3- 氟 - 苯基 ] 乙烯基 ]-6- 甲基 -1,3,6,2- 二氧氮硼雜八環 -4,8- 二酮
將5-苄氧基-4-(2-溴-3-氯-6-氟-苯基)-2,6-二甲基-嗒𠯤-3-酮(1.00 g,2.28 mmol)、氯[(三三級丁基膦)-2-(2-胺基聯苯基)]鈀(II)(59 mg,0.11 mmol)、N,N-二異丙基乙胺(0.80 mL,4.57 mmol)和6-甲基-2-乙烯基-1,3,6,2-二氧氮硼雜八環-4,8-二酮(0.50 g,2.74 mmol)在THF(23 mL)中的攪拌溶液在90°C下加熱5小時,然後在70°C下加熱另外16小時。
將反應混合物冷卻至室溫,然後用DCM稀釋並通過Celite®過濾,用另外部分的DCM洗提。將濾液在真空中濃縮,然後藉由快速管柱層析法(二氧化矽,洗提液:乙酸乙酯/甲醇梯度)純化以給出5-苄氧基-4-(2-溴-3-氯-6-氟-苯基)-2,6-二甲基-嗒𠯤-3-酮;2-[(E)-2-[2-(5-苄氧基-2,6-二甲基-3-側氧基-嗒𠯤-4-基)-6-氯-3-氟-苯基]乙烯基]-6-甲基-1,3,6,2-二氧氮硼雜八環-4,8-二酮(904 mg,74%產率)。
1
H NMR (400 MHz, CDCl3
) δ ppm 2.26 (s, 3 H) 2.79 (s, 3 H) 3.73 (s, 7 H) 4.60 (s, 2 H) 5.97 (d, J=18.6 Hz, 1 H) 6.76 (d, J=18.5 Hz, 1 H) 7.02 (t, J=8.6 Hz, 1 H) 7.09 (dd, J=6.7, 3.00 Hz, 2 H) 7.29 - 7.34 (m, 3 H) 7.44 (dd, J=8.9, 5.1 Hz, 1 H)。
2.3 5-
苄氧基
-4-[3-
氯
-6-
氟
-2-[(E)-2-(1H-
吲哚
-5-
基
)
乙烯基
]
苯基
]-2,6-
二甲基
-
嗒
𠯤
-3-
酮
向微波小瓶中添加2-[(E)-2-[2-(5-苄氧基-2,6-二甲基-3-側氧基-嗒𠯤-4-基)6-氯-3-氟-苯基]乙烯基]-6-甲基-1,3,6,2-二氧氮硼雜八環-4,8-二酮(300 mg,0.56 mmol)、5-溴-1H-吲哚(163 mg,0.84 mmol)、Pd(dppf)Cl2
.DCM(23 mg,0.028 mmol)和K3
PO4
.H2
O(512 mg,2.22 mmol)。然後將小瓶加蓋並用N2
吹掃,然後添加THF(5.6 mL)和水(0.2 mL)。然後在微波輻射下,將反應混合物加熱至90°C持續30分鐘。
將反應混合物冷卻至室溫,然後在水(20 mL)與EtOAc(20 mL)之間分配。分離有機層並且用EtOAc(2 × 20 mL)萃取水層。將合併的有機物收集、乾燥(MgSO4)、過濾並在真空中濃縮以給出粗產物。
將粗產物藉由質量定向的逆相製備型HPLC純化以給出5-苄氧基-4-[3-氯-6-氟-2-[(E)-2-(1H-吲哚-5-基)乙烯基]苯基]-2,6-二甲基-嗒𠯤-3-酮(45 mg,16%產率)。
1
H NMR (400 MHz, CDCl3
) δ ppm 2.20 (s, 3 H) 3.76 (s, 3 H) 4.70 (d, J=5.3 Hz, 2 H) 6.53 (t, J=2.1 Hz, 1 H) 6.78 - 6.86 (m, 1 H) 6.88 - 6.94 (m, 1 H) 7.01 (t, J=8.6 Hz, 1 H) 7.12 - 7.17 (m, 2 H) 7.19 (t, J=2.8 Hz, 1 H) 7.21 - 7.25 (m, 1 H) 7.29 - 7.35 (m, 4 H) 7.47 (dd, J=8.9, 5.3 Hz, 1 H) 7.55 (s, 1 H) 8.25 - 8.44 (m, 1 H)。
2.4 4-[3-
氯
-6-
氟
-2-[2-(1H-
吲哚
-5-
基
)
乙基
]
苯基
]-5-
羥基
-2,6-
二甲基
-
嗒
𠯤
-3-
酮
(A-1.021)
使5-苄氧基-4-[3-氯-6-氟-2-[(E)-2-(1H-吲哚-5-基)乙烯基]苯基]-2,6-二甲基-嗒𠯤-3-酮(45 mg,0.09 mmol)在3巴H2
下在四氫呋喃(0.23 mL)中在5% Pd/C催化劑(38 mg × 2)上經受催化氫化。
完成後,將反應混合物通過Celite®墊過濾,用DCM洗提。將濾液在真空中濃縮以得到粗殘餘物。
將殘餘物吸附到二氧化矽上並藉由快速管柱層析法(二氧化矽,洗提液:乙酸乙酯/異己烷)純化以給出4-[3-氯-6-氟-2-[2-(1H-吲哚-5-基)乙基]苯基]-5-羥基-2,6-二甲基-嗒𠯤-3-酮(24 mg,65%產率,A-1.021
)。
1
H NMR (400 MHz, CDCl3
) δ ppm 2.18 (s, 3 H) 2.70 - 2.96 (m, 4 H) 3.69 (s, 3 H) 6.44 (ddd, J=3.0, 2.0, 0.7 Hz, 1 H) 6.78 (dd, J=8.3, 1.6 Hz, 1 H) 6.89 (t, J=8.6 Hz, 1 H) 7.14 - 7.18 (m, 1 H) 7.18 - 7.26 (m, 2 H) 7.37 (dd, J=8.8, 5.14 Hz, 1 H) 8.21 (br s, 1 H)。
3.1 2-
甲基丙酸
[5-[3-
氯
-6-
氟
-2-[(E)-2-(6-
甲基
-4,8-
二側氧基
-1,3,6,2-
二氧氮硼雜八環
-2-
基
)
乙烯基
]
苯基
]-1,3-
二甲基
-6-
側氧基
-
嗒
𠯤
-4-
基
]
酯
將2-甲基-丙酸[5-(2-溴-3-氯-6-氟-苯基)-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(5.00 g,11.97 mmol,1.0當量)、6-甲基-2-乙烯基-1,3,6,2-二氧氮硼雜八環-4,8-二酮(2.63 g,14.36 mmol,1.2當量)和氯[(三三級丁基膦)-2-(2-胺基聯苯基)]鈀(II)(307 mg,0.60 mmol,0.05當量)裝入裝配有冷凝器、攪拌棒和氮氣鼓泡器的250 ml圓底燒瓶中。添加THF(100 mL),接著針對氮氣流添加N,N-二異丙基乙胺(4.2 mL,23.94 mmol,2.0當量)並將混合物加熱至回流持續3 h。
將反應混合物冷卻至室溫,然後在DCM中稀釋並通過Celite®過濾,用另外部分的DCM洗滌。然後將洗提液濃縮至乾燥。
將粗產物藉由快速管柱層析法進行純化,以得到呈灰白色固體的2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(6-甲基-4,8-二側氧基-1,3,6,2-二氧氮硼雜八環-2-基)乙烯基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(5.91 g,11.4 mmol,95%產率)。
1
H NMR (400 MHz, DMSO-d6
) δ = 7.63 (dd, J = 5.1, 8.9 Hz, 1H), 7.31 (t, J = 8.9 Hz, 1H), 6.65 (d, J = 18.3 Hz, 1H), 5.68 (d, J = 18.3 Hz, 1H), 4.24 (dd, J = 11.9, 17.2 Hz, 2H), 3.95 - 3.83 (m, 2H), 3.70 (s, 3H), 2.66 (spt, J = 7.0 Hz, 1H), 2.16 (s, 3H), 0.90 (d, J = 7.0 Hz, 3H), 0.89 (d, J = 7.0 Hz, 3H)
3.2 2-
甲基丙酸
[5-[3-
氯
-6-
氟
-2-[(E)-2-(3-
甲基苯并三唑
-5-
基
)
乙烯基
]
苯基
]-1,3-
二甲基
-6-
側氧基
-
嗒
𠯤
-4-
基
]
酯
(4.343)
將2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(6-甲基-4,8-二側氧基-1,3,6,2-二氧氮硼雜八環-2-基)乙烯基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(700 mg,1.35 mmol)、1,1-雙(二苯基膦基)二茂鐵]二氯鈀(II)二氯甲烷錯合物 [PdCl2(dppf).DCM](55 mg,0.067 mmol)、6-溴-1-甲基-苯并三唑(371 mg,1.75 mmol)和磷酸鉀(1.17 g,5.39 mmol)添加到10-20 ml微波小瓶中。添加2-甲基四氫呋喃(10 ml)和水(0.5 ml),然後藉由抽空將反應混合物脫氣並且回填氮氣(X3)。在微波輻射下,將反應混合物加熱至120°C持續60分鐘。
將反應混合物通過Celite®塞過濾,用EtOAc和EtOH洗滌。將濾液在減壓下濃縮以給出棕色膠狀物(853 mg)。將粗材料藉由自動矽膠快速層析法(用環己烷/乙酸乙酯梯度洗提)純化以給出呈橙色膠狀物的2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(3-甲基苯并三唑-5-基)乙烯基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(4.343)
(622 mg,87%產率)
將經純化的材料溶解於乙腈(10 ml)並在室溫下用SiliCycle SiliaMetS®硫醇(SH)金屬清除劑樹脂(622 mg)進行處理。將懸浮液在室溫下攪拌1.5 h,然後過濾以除去樹脂,用另外的乙腈洗滌。將濾液在真空中濃縮以提供呈白色固體的2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(3-甲基苯并三唑-5-基)乙烯基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(4.343)
(583 mg,87%產率)
1
H NMR(400 MHz, 氯仿) 7.96 (d, J=9.0 Hz,1H), 7.39 - 7.49 (m, 3H), 7.15 (d, J=16.3 Hz,1H), 7.05 (t, J=8.7 Hz, 1H), 6.81 (d, J=16.3 Hz, 1H), 4.29 (s, 3H), 3.68 (s, 3H), 2.67(spt, J=7.0 Hz, 1H), 2.23 (s, 3H), 1.13 (d, J=7.0 Hz, 3H), 1.09 (d, J=7.0 Hz, 3H)
3.3 2-
甲基丙酸
[5-[3-
氯
-6-
氟
-2-[2-(3-
甲基苯并三唑
-5-
基
)
乙基
]
苯基
]-1,3-
二甲基
-6-
側氧基
-
嗒
𠯤
-4-
基
]
酯
使2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(3-甲基苯并三唑-5-基)乙烯基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(496 mg,1.00 mmol)在3巴H2
下在EtOAc(10 mL)中在5% Pd/C(50%濕)催化劑(0.21 g)上經受催化氫化持續18 h。
將反應混合物通過Celite®墊過濾,用乙酸乙酯洗滌。將濾液在真空中濃縮以得到粗殘餘物(503 mg),將其藉由質量定向的逆相HPLC純化以得到呈無色膠狀物的2-甲基丙酸[5-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(332 mg,67%產率)
1
H NMR (400 MHz, 氯仿) δ = 7.92 (d, J = 8.6 Hz, 1H), 7.43 (dd, J = 5.1, 8.7 Hz, 1H), 7.24 (br s, 1H), 7.17 (dd, J = 1.3, 8.6 Hz, 1H), 7.01 (t, J = 8.7 Hz, 1H), 4.26 (s, 3H), 3.81 (s, 3H), 3.11 - 2.91 (m, 3H), 2.86 - 2.72 (m, 1H), 2.54 (spt, J = 7.0 Hz, 1H), 2.25 (s, 3H), 0.98 (d, J = 7.1 Hz, 3H), 0.96 (d, J = 7.0 Hz, 3H)
3.4 4-[3-
氯
-6-
氟
-2-[2-(3-
甲基苯并三唑
-5-
基
)
乙基
]
苯基
]-5-
羥基
-2,6-
二甲基
-
嗒
𠯤
-3-
酮
(1.343)
的製備
在室溫下在乙醇(5 ml)中攪拌2-甲基丙酸[5-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(332 mg,0.67 mmol)。逐滴地添加氫氧化鋰一水合物(85 mg,2.00 mmol)在水中(2 ml)的溶液,並將反應在室溫下攪拌21 h。
將乙醇溶劑在減壓下除去,然後用水(20 ml)稀釋殘餘物。藉由添加2 M HCl(水性)將水相酸化至大約pH 3-4,然後將其用EtOAc(3 × 10 ml)萃取。將合併的有機萃取物在減下壓濃縮以給出白色固體(240 mg)。將粗殘餘物藉由自動矽膠快速層析法(用環己烷/乙酸乙酯梯度洗提)純化以得到呈白色固體的4-[3-氯-6-氟-2-[2-(3-甲基苯并三唑-5-基)乙基]苯基]-5-羥基-2,6-二甲基-嗒𠯤-3-酮(1.343)
(196 mg,69%)
1
H NMR (400 MHz, 乙腈) δ ppm 7.83 (d, J=8.6 Hz, 1H), 7.57 (dd, J=5.2, 8.8 Hz, 1H), 7.33 (s, 1H), 7.10 - 7.18 (m, 2H), 4.22 (s, 3H), 3.64 (s, 3H), 2.84 - 3.07 (m, 4H) 2.21 (s, 3H)
4.1 4-[2-[(E)-2-(1,3-
苯并噻唑
-5-
基
)
乙烯基
]-3-
氯
-6-
氟
-
苯基
]-5-
羥基
-2,6-
二甲基
-
嗒
𠯤
-3-
酮
將2-甲基丙酸[5-[3-氯-6-氟-2-[(E)-2-(6-甲基-4,8-二側氧基-1,3,6,2-二氧氮硼雜八環-2-基)乙烯基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(500 mg,0.96 mmol)、5-溴-1,3-苯并噻唑(309 mg,1.44 mmol)、1,1-雙(二苯基膦基)二茂鐵]二氯鈀(II)二氯甲烷錯合物 [PdCl2(dppf).DCM](4 mg,0.05 mmol)和碳酸鉀(403 mg,2.89 mmol)在氮氣氣氛下添加到10-20 ml微波小瓶中。添加經脫氣的乙腈(8 ml)和水(2 ml)並將混合物在微波輻射下加熱至150°C持續30分鐘。
將反應混合物濃縮至乾燥。將殘餘物用水(10 ml)處理,並藉由添加1 M HCl(水性)將水相酸化至pH 4。添加DCM(20 ml)並且分離層。將水相用DCM/MeOH(8 : 1)(2 × 10 ml)進一步萃取,然後將合併的有機萃取物乾燥並濃縮以給出棕色油狀物。將粗材料藉由自動矽膠快速層析法(用環己烷/乙酸乙酯梯度洗提)純化以給出呈白色固體的4-[2-[(E)-2-(1,3-苯并噻唑-5-基)乙烯基]-3-氯-6-氟-苯基]-5-羥基-2,6-二甲基-嗒𠯤-3-酮(302 mg,73%產率)。
將獲得的產物溶解在甲醇/乙酸乙酯的3 : 2混合物(25 ml)中。將溶液用活性炭(100 mg)處理,然後在室溫下攪拌1 h。將混合物通過celite®過濾,然後用額外的3 : 2 MeOH/EtOAc(10 ml)洗滌。將濾液用SiliCycle SiliaMetS®硫醇(SH)金屬清除劑樹脂(300 mg)處理,然後在室溫下攪拌16 h。過濾混合物以除去樹脂,然後將濾液在真空中濃縮以給出灰白色固體(286 mg)。
1
H NMR (400 MHz, DMSO-d6) δ = 10.84 (br s, 1H), 9.41 (s, 1H), 8.14 (d, J = 8.4 Hz, 1H), 8.00 (d, J = 1.5 Hz, 1H), 7.62 (dd, J = 5.1, 8.7 Hz, 1H), 7.54 (dd, J = 1.5, 8.4 Hz, 1H), 7.29 (t, J = 8.7 Hz, 1H), 7.09 (d, J = 16.5 Hz, 1H), 6.74 (d, J = 16.5 Hz, 1H), 3.54 (s, 3H), 2.18 (s, 3H)
4.2 4-[2-[2-(1,3-
苯并噻唑
-5-
基
)
乙基
]-3-
氯
-6-
氟
-
苯基
]-5-
羥基
-2,6-
二甲基
-
嗒
𠯤
-3-
酮
(1.350)
向氮氣氛下的4-[2-[(E)-2-(1,3-苯并噻唑-5-基)乙烯基]-3-氯-6-氟-苯基]-5-羥基-2,6-二甲基-嗒𠯤-3-酮(835 mg,1.95 mmol)在四氫呋喃(30 ml)中的溶液中添加N,N-二異丙基乙胺(2.70 ml,16.0 mmol)。將攪拌的反應混合物加熱至70°C並將2,4,6-三異丙基苯磺醯基醯肼(5.17 g,15.6 mmol)在4 h內分批添加,然後將混合物加熱至回流持續16 h。將額外的N,N-二異丙基乙胺(1.70 ml,9.80 mmol)添加到反應混合物中,接著添加2,4,6-三異丙基苯磺醯基醯肼(3.24 g,9.77 mmol),並將混合物加熱至回流持續另外的6 h。
將反應混合物冷卻至室溫,然後直接濃縮到二氧化矽上。將粗材料藉由自動矽膠快速層析法(用環己烷/乙酸乙酯梯度洗提)部分純化。將所獲得的材料藉由質量定向的逆相HPLC進一步純化以得到呈淡黃色固體的4-[3-氯-6-氟-2-[2-[4-(甲基氫硫基甲基)苯基]乙基]苯基]-5-羥基-2,6-二甲基-嗒𠯤-3-酮(1.350)
(227 mg,27%產率)
1HNMR (500 MHz,DMSO-d6) δ ppm 10.84 (br. s,1H), 9.35 (s,1H), 8.03 (d, J=8.3 Hz,1H), 7.71 (d, J=1.0 Hz,1H), 7.55 (dd, J=5.2, 8.8 Hz,1H), 7.23 (t, J=8.8 Hz,1H), 7.16 (dd, J=1.0, 8.3 Hz, 1H), 3.62 (s, 3H), 2.93 - 2.70 (m,4 H), 2.26 (s, 3H)
實施例
5 [3-
氯
-2-[2-(2,2-
二甲基
-1,3-
苯并間二氧雜環戊烯
-5-
基
)
乙基
]-6-
氟
-
苯基
]-5-
羥基
-2,6-
二甲基
-
嗒
𠯤
-3-
酮
(1.361)
之製備
5.1 2-
甲基丙酸
[5-[3-
氯
-6-
氟
-2-[2-(4,4,5,5-
四甲基
-1,3,2-
二氧雜環戊硼烷
-2-
基
)
乙基
]
苯基
]-1,3-
二甲基
-6-
側氧基
-
嗒
𠯤
-4-
基
]
酯
將經烘箱乾燥的圓底燒瓶然後裝入Ir(COD)Cl2
(299 mg,0.45 mmol)和4-二苯基磷烷基丁基(二苯基)磷烷(0380 mg,0.89 mmol)。將燒瓶排空並回填氮氣(x 3),然後添加THF(75 mL)並將反應在室溫下攪拌30分鐘。逐滴地添加2-甲基丙酸[5-(3-氯-6-氟-2-乙烯基-苯基)-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯[如在實施例4中所述之製備](6.7 g,17.8 mmol)在THF中的溶液並將混合物攪拌10分鐘,接著逐滴地添加4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷(3.02 mL,20.8 mmol)。將反應在60°C下攪拌過夜。
24 h後,將反應冷卻至室溫,然後在真空中濃縮。將粗產物藉由矽膠管柱層析法(用環己烷/乙酸乙酯梯度洗提)純化以給出呈黃色固體的2-甲基丙酸[5-[3-氯-6-氟-2-[2-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)乙基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(4.50 g,51%產率)。
1
H NMR (500 MHz, 氯仿) δ = 7.35 (dd, J = 5.2, 8.9 Hz, 1H), 6.90 (t, J = 8.6 Hz, 1H), 3.81 (s, 3H), 2.59 (t, J = 8.5 Hz, 2H), 2.53 (spt, J = 7.0 Hz, 1H), 2.24 (s, 3H), 1.32 - 1.16 (m, 12H), 1.08 - 1.00 (m, 2H), 0.98 (d, J = 7.0 Hz, 3H), 0.94 (d, J = 7.0 Hz, 3H)。
5.2 [3-
氯
-2-[2-(2,2-
二甲基
-1,3-
苯并間二氧雜環戊烯
-5-
基
)
乙基
]-6-
氟
-
苯基
]-5-
羥基
-2,6-
二甲基
-
嗒
𠯤
-3-
酮
(1.361)
將5-溴-2,2-二甲基-1,3-苯并間二氧雜環戊烯(70 mg,0.30 mmol)裝入2-5 ml的微波小瓶中。作為在1,4-二㗁𠮿(2 ml)中的溶液添加2-甲基丙酸[5-[3-氯-6-氟-2-[2-(4,4,5,5-四甲基-1,3,2-二氧雜環戊硼烷-2-基)乙基]苯基]-1,3-二甲基-6-側氧基-嗒𠯤-4-基]酯(100 mg,0.20 mmol),接著作為在1,4-二㗁𠮿(2 ml)中的溶液添加氯(2-二環己基膦基-2’,6’-二異丙氧基-1,1’-聯苯基)[2-(2’-胺基-1,1’-聯苯基)]鈀(II)(RuPhos Pd-G2)(26 mg,0.03 mmol)。添加碳酸鉀的2 M水溶液(0.30 ml,0.61 mmol),並將混合物在微波輻射下加熱至140°C持續80分鐘。
將反應混合物冷卻至室溫,然後藉由預先潤濕的0.5 g Silica-TMT管柱過濾,用乙腈(2 × 2 ml)洗滌。將濾液濃縮至乾燥,然後藉由質量定向的逆相HPLC純化以得到呈白色固體的[3-氯-2-[2-(2,2-二甲基-1,3-苯并間二氧雜環戊烯-5-基)乙基]-6-氟-苯基]-5-羥基-2,6-二甲基-嗒𠯤-3-酮(1.361)
(15 mg,17%產率)。
1
H NMR (500 MHz, 氯仿) δ ppm 7.43 (dd, J = 5.2, 8.7 Hz, 1H), 6.99 (t, J = 8.7 Hz, 1H), 6.56 (d, J = 7.7 Hz, 1H), 6.40 - 6.36 (m, 2H), 3.74 (s, 3H), 2.85 - 2.78 (m, 1H), 2.77 - 2.61 (m, 3H), 2.30 (s, 3H), 1.65 (s, 3H), 1.64 (s, 3H)
使用如上所述之通用方法製備化合物1.019、1.021、1.027、1.028、1.036、2.034、3.030、3.034、4.034、1.339、1.340、1.341、1.342、、1.344、1.345、1.346、1.347、1.348、1.349、1.351、1.352、1.353、1.354、1.355、1.356、1.044、1.053、1.357、1.358、1.359、1.360、2.362、2.363、和4.342。下表5示出了該等化合物的結構和NMR表徵數據。
[ 表 5]
具有式 (I) 之化合物的製備實施例。用於描述X和Y的位置的編號系統僅為清楚起見而示出。
化合物編號 | R1 | R2 | G | X | Y | W | D | NMR 詳情 |
1.019 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 1,2,3,4-四氫喹啉-6-基- | 1 H NMR (400 MHz, 氯仿) δ ppm 1.91 (br d, J=5.26 Hz, 3 H) 2.30 (s, 3 H) 2.50 - 2.84 (m, 5 H) 3.19 - 3.30 (m, 2 H) 3.46 (s, 1 H) 3.73 (s, 3 H) 6.35 (d, J=8.56 Hz, 1 H) 6.57 - 6.65 (m, 2 H) 6.97 (t, J=8.56 Hz, 1 H) 7.41 (dd, J=8.80, 5.14 Hz, 1 H) |
1.021 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 1H-吲哚-5-基- | 1 H NMR (400 MHz, 氯仿) δ ppm 2.18 (s, 3 H) 2.70 - 2.96 (m, 4 H) 3.69 (s, 3 H) 6.44 (ddd, J=3.00, 2.02, 0.73 Hz, 1 H) 6.78 (dd, J=8.31, 1.59 Hz, 1 H) 6.89 (t, J=8.56 Hz, 1 H) 7.14 - 7.18 (m, 1 H) 7.18 - 7.26 (m, 2 H) 7.37 (dd, J=8.80, 5.14 Hz, 1 H) 8.21 (br s, 1 H) |
1.027 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2-(三氟甲基)-4-喹啉基- | 1 H NMR (400 MHz, 氯仿) δ ppm 2.28 (s, 3 H) 2.81 - 2.94 (m, 1 H) 3.01 (br d, J=6.11 Hz, 1 H) 3.35 (s, 2 H) 3.75 (s, 3 H) 7.04 (t, J=8.56 Hz, 1 H) 7.42 - 7.49 (m, 2 H) 7.58 (ddd, J=8.31, 6.97, 1.10 Hz, 1 H) 7.79 (ddd, J=8.41, 6.94, 1.28 Hz, 1 H) 7.86 (d, J=8.07 Hz, 1 H) 8.20 (d, J=8.56 Hz, 1 H) |
1.028 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2-乙基-1,3-苯并㗁唑-6-基- | 1 H NMR (400 MHz, 甲醇) δ = 7.49 (dd, J = 5.3, 8.8 Hz, 1H), 7.40 (d, J = 8.3 Hz, 1H), 7.26 (d, J = 1.2 Hz, 1H), 7.08 (t, J = 8.8 Hz, 1H), 7.02 (dd, J = 1.2, 8.3 Hz, 1H), 3.73 (s, 3H), 2.96 (q, J = 7.6 Hz, 2H), 2.91 - 2.74 (m, 4H), 2.33 (s, 3H), 1.42 (t, J = 7.6 Hz, 3H) |
1.036 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 4-喹啉基- | 1 H NMR (400 MHz, 氯仿) δ ppm 2.28 (s, 3 H) 2.88 - 3.02 (m, 2 H) 3.24 (ddd, J=19.47, 10.48, 6.24 Hz, 2 H) 3.74 (s, 3 H) 7.00 (t, J=8.56 Hz, 1 H) 7.17 (d, J=4.52 Hz, 1 H) 7.38 - 7.51 (m, 2 H) 7.64 - 7.79 (m, 2 H) 8.03 (d, J=8.19 Hz, 1 H) 8.65 (d, J=4.40 Hz, 1 H) |
2.034 | -Me | -Me | -H | 6-F | 3-Cl | (E)-CH=CH- | 2-甲基-6-喹啉基- | 1 H NMR (400 MHz, 溶劑) δ ppm 1.11 (t, J=7.15 Hz, 6 H) 2.23 (s, 3 H) 2.63 - 2.71 (m, 1 H) 2.74 (s, 3 H) 3.69 (s, 3 H) 6.81 (d, J=16.38 Hz, 1 H) 7.04 (t, J=8.68 Hz, 1 H) 7.15 (d, J=16.51 Hz, 1 H) 7.27 (s, 1 H) 7.45 (dd, J=8.86, 5.07 Hz, 1 H) 7.63 (d, J=1.71 Hz, 1 H) 7.75 - 7.81 (m, 1 H) 7.94 (d, J=8.80 Hz, 1 H) 8.01 (d, J=8.31 Hz, 1 H) |
3.030 | -Me | -Me | -(C=O)iPr | 6-F | 3-Cl | -CH2 -CH2 - | 2-甲基-1,2,3,4-四氫喹啉-6-基- | 1 H NMR (400 MHz, 溶劑) δ ppm 0.96 (dd, J=7.03, 2.02 Hz, 6 H) 1.25 (d, J=6.24 Hz, 3 H) 1.58 - 1.69 (m, 1 H) 1.90 - 1.98 (m, 1 H) 2.24 (s, 3 H) 2.54 (dt, J=13.94, 6.97 Hz, 1 H) 2.63 - 2.84 (m, 6 H) 3.39 (td, J=6.51, 3.12 Hz, 1 H) 3.83 (s, 3 H) 6.52 (br d, J=6.48 Hz, 1 H) 6.72 - 6.79 (m, 2 H) 6.96 (t, J=8.62 Hz, 1 H) 7.40 (dd, J=8.80, 5.14 Hz, 1 H) |
3.034 | -Me | -Me | -(C=O)iPr | 6-F | 3-Cl | -CH2 -CH2 - | 2-甲基-6-喹啉基- | 1 H NMR (400 MHz, 溶劑) δ ppm 0.97 (dd, J=6.97, 4.40 Hz, 6 H) 2.24 (s, 3 H) 2.47 - 2.57 (m, 1 H) 2.73 (s, 3 H) 2.79 - 3.09 (m, 4 H) 3.84 (s, 3 H) 7.00 (t, J=8.62 Hz, 1 H) 7.25 (d, J=8.31 Hz, 1 H) 7.49 (d, J=1.10 Hz, 3 H) 7.90 (d, J=8.44 Hz, 1 H) 7.96 (d, J=8.31 Hz, 1 H) |
4.034 | -Me | -Me | -(C=O)iPr | 6-F | 3-Cl | (E)-CH=CH- | 2-甲基-6-喹啉基- | 1 H NMR (400 MHz, 溶劑) δ ppm 2.24 (s, 3 H) 2.66 (s, 3 H) 3.66 (s, 3 H) 6.72 (d, J=16.38 Hz, 1 H) 6.93 - 7.07 (m, 2 H) 7.26 (s, 1 H) 7.38 (dd, J=8.93, 5.14 Hz, 1 H) 7.55 (d, J=1.71 Hz, 1 H) 7.66 (dd, J=8.80, 1.96 Hz, 1 H) 7.84 (d, J=8.80 Hz, 1 H) 7.99 (d, J=8.44 Hz, 1 H) |
1.339 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2-甲基-5-1,3-苯并噻唑基- | 1 H NMR (500 MHz, 氯仿) δ ppm 7.64 (d, J = 8.1 Hz, 1H), 7.52 (br s, 1H), 7.19 (dd, J = 5.1, 8.6 Hz, 1H), 7.01 (br d, J = 8.1 Hz, 1H), 6.92 (t, J = 8.6 Hz, 1H), 3.80 (s, 3H), 2.90 - 2.74 (m, 4H), 2.69 (s, 3H), 2.32 (s, 3H) |
1.340 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2,2-二甲基-6-3H-苯并呋喃基- | 1 H NMR (400 MHz, 甲醇) δ ppm 7.50 (dd, J=5.1, 8.8 Hz,1H), 7.08 (t, J=8.8 Hz,1H), 6.97(d, J=7.5 Hz,1H), 6.44(dd, J=1.2, 7.5 Hz,1H), 6.29 (d, J=1.2 Hz,1H), 3.73 (s, 3H), 2.93 (s, 2H), 2.79 - 2.50 (m, 4H), 2.33 (s, 3H), 1.41 (s, 6H) |
1.341 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2-甲基-6-1,3-苯并㗁唑基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.83 (br.s, 1H), 7.54 (dd,J=5.2, 8.9 Hz,1H), 7.50 (d, J=8.1 Hz, 1H), 7.24 (d, J=1.4 Hz, 1H), 7.22 (t, J=8.9 Hz, 1H), 6.96 (dd, J=1.4, 8.1 Hz, 1H), 3.61 (s, 3H), 2.87 - 2.66 (m, 4H) ,2.57 (s, 3H), 2.25 (s, 3H) |
1.342 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- | 1 H NMR (400 MHz, 氯仿) δ ppm 7.38 (dd, J=8.8, 5.1 Hz, 1H), 6.94 (t, J=8.8 Hz, 1H), 6.87 (d, J=8.1 Hz, 1H), 6.70-6.63 (m, 2H), 3.68 (s, 3H), 2.76 - 2.65 (m, 4H), 2.26 (s, 3H) |
1.344 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 1-甲基-3-吲唑基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.86 (s, 1H), 7.59 - 7.53 (m, 2H), 7.34 (t, J=7.2 Hz, 1H), 7.27 - 7.21 (m, 2H), 7.02 (t, J=7.2 Hz, 1H), 3.93 (s, 3H), 3.58 (s, 3H), 2.99 - 2.92 (m, 2H), 2.87 - 2.83 (m, 2H), 2.23 (s. 3H) |
1.345 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 1-甲基-5-吡咯并[2,3-b]吡啶基- | 1 H NMR (400 MHz, 甲醇) δ ppm 8.12 (d, J=1.7 Hz, 1H), 7.95 (d, J=1.7 Hz, 1H), 7.52 (d, J=3.5 Hz, 1H), 7.46 (dd, J=5.1, 8.8 Hz, 1H), 7.10 (t, J=8.8 Hz, 1H), 6.64 (d, J=3.5 Hz, 1H), 3.93 (s, 3H), 3.63 (s, 3H), 3.11 - 2.99 (m, 2H), 2.98 - 2.82 (m, 2H), 2.30 (s, 3H) |
1.346 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 5-苯并呋喃基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.82 (s, 1H), 7.93 (d, J=1.8 Hz,1H), 7.57-7.53 (m, 1H), 7.45 (d, J=8.4 Hz,1H), 7.28 (br. s, 1H), 7.21 (t, J=8.5 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 6.87 (br. s, 1H), 3.61 (s, 3H), 2.76-2.67 (m, 4H), 2.25 (s, 3H) |
1.347 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 6-苯并噻吩基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.83 (s, 1H), 7.87 (d, J=8.24 Hz, 1H), 7.72 (d, J=5.4 Hz,1H), 7.58 - 7.54 (m, 1H), 7.52 (s, 1H), 7.37 (d, J=5.4 Hz, 1H), 7.22 (t, J=8.8 Hz, 1H), 7.00 (d, J=8.24 Hz, 1H), 3.61 (s, 3H), 2.79 - 2.69 (m, 4H), 2.25 (s. 3H) |
1.348 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 5-苯并噻吩基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.83 (s, 1H), 7.86 (m, 1H), 7.72 (m, 1H), 7.58-7.52 (m, 2H), 7.37 (m, 1H), 7.22 (m, 1H), 7.01 - 6.98 (m, 1H), 3.61 (s, 3H), 2.79 - 2.71 (m, 4H), 2.25 (s, 3H) |
1.349 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 6-1,3-苯并噻唑基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.81 (s, 1H), 9.30 (s, 1H), 7.95 (d, J=8.3 Hz, 1H), 7.81 (s, 1H), 7.57 - 7.53 (m, 1H), 7.24 - 7.16 (m, 2H), 3.59 (s, 3H), 2.82-2.73 (m, 4H), 2.24 (s. 3H) |
1.351 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 3-甲基-6-1,2-苯并㗁唑基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.81 (s, 1H), 7.70 (d, J=8.04 Hz, 1H), 7.54 (m, 1H), 7.29 (s, 1H), 7.21 (t, J=8.7 Hz, 1H), 7.01 (d, J=8.04 Hz, 1H), 3.60 (s, 3H), 2.86 - 2.73 (m, 4H), 2.50 (s, 3H), 2.24 (s. 3H) |
1.352 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 5-2-側氧基-3H-1,3-苯并㗁唑基- | 1 H NMR (400 MHz, 甲醇) δ ppm 7.49 (dd, J=5.1, 8.8 Hz, 1H), 7.09 (t, J=8.8 Hz, 1H), 7.04 (d, J=8.2 Hz, 1H), 6.74 (dd, J=1.5, 8.2 Hz, 1H), 6.71 (d, J=1.5 Hz, 1H), 3.72 (s, 3H), 2.88 - 2.65 (m, 4H), 2.32 (s, 3H) |
1.353 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 6-1-甲基吲唑基- | 1 H NMR (400 MHz, 甲醇) δ ppm 7.90 (d, J=1.0 Hz, 1H), 7.58 (dd, J=0.6, 8.3 Hz, 1H), 7.51 (dd, J=5.1, 8.8 Hz, 1H), 7.10 (br. s, 1H), 7.11 (t, J=8.8 Hz, 1H), 6.81 (dd, J=1.0, 8.3 Hz, 1H), 3.98 (s, 3H), 3.68 (s, 3H), 2.99 - 2.77 (m, 4H), 2.27 (s, 3H) |
1.354 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 5-1-甲基吲唑基- | 1 H NMR (400 MHz, 甲醇) 7.86 (s, 1H), 7.49 (dd, J=5.1, 8.8 Hz, 1H), 7.38 (d, J=8.6 Hz, 1H), 7.35 (s, 1H), 7.09 (t, J=8.8 Hz, 1H), 7.07 (d, J=8.6 Hz, 1H), 4.00 (s, 3H), 3.70 (s, 3H), 2.92-2.74 (m, 4H), 2.30 (s, 3H) |
1.355 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 6-1-甲基吲哚基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.85 (s, 1H), 7.58 - 7.55 (m, 1H), 7.40 (d,1H), 7.23 - 7.20 (m, 2H), 6.93 (s, 1H), 6.66 (d, 1H), 6.33 (d, 1H), 3.71 (s, 3H), 3.62 (s, 3H), 2.76 - 2.68 (m, 4H), 2.26 (s, 3H) |
1.356 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 5-1-甲基吲哚基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.83 (s, 1H), 7.57 - 7.54 (m, 1H), 7.33 - 7.29 (m,1H), 7.26 (d,1H), 7.21 (t, 1H), 7.15 (s, 1H), 6.76 (d, 1H), 6.31 (d, 1H), 3.73 (s, 3H), 3.61 (s, 3H), 2.72 - 2.64 (m, 4H), 2.27 (s, 3H) |
1.044 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 1-萘基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.96 (s, 1H), 7.91 (d, J=8.2 Hz, 1H), 7.77 (d, J=8.2 Hz, 1H), 7.63 - 7.59 (m, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.50 (t, J=7.6 Hz, 1H), 7.44-7.36 (m, 2H), 7.28-7.23 (m, 2H), 3.64 (s, 3H), 3.12 - 3.03 (m, 2H), 2.80 - 2.72 (m, 2H), 2.28 (s. 3H) |
1.053 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2-萘基- | 1 H NMR (400 MHz, DMSO-d6) δ ppm 10.85 (s, 1H), 7.86 - 7.78 (m, 3H), 7.58-7.55 (m, 1H), 7.51 - 7.42 (m, 3H), 7.23 (t, J=8.7 Hz, 1H), 7.16-7.14 (1H), 3.61 (s, 3H), 2.88 - 2.72 (m, 4H), 2.25 (s, 3H) |
1.357 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 5-2-側氧基吲哚啉基- | 1 HNMR (400 MHz, DMSO-d6) 10.82 (br. s, 1H), 10.28 (s, 1H), 7.55 (dd, J=5.3, 8.7 Hz, 1H), 7.21 (t, J=8.7 Hz, 1H), 6.85 (br. s, 1H), 6.79 (br.d, J=7.8 Hz, 1H), 6.68 (d, J=7.8 Hz, 1H), 3.61 (s, 3H), 3.40 (s, 2H), 2.73 - 2.52 (m, 4H), 2.26 (s, 3H) |
1.358 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2-甲基-1,3-二側氧基-異吲哚啉-5-基- | 1 H NMR (500 MHz, 氯仿) δ ppm 7.68 (d, J = 7.6 Hz, 1H), 7.52 (br s, 1H), 7.45 (dd, J = 5.2, 8.7 Hz, 1H), 7.39 - 7.34 (m, 1H), 7.05 (t, J = 8.7 Hz, 1H), 3.78 (s, 3H), 3.15 (s, 3H), 3.04 - 2.85 (m, 3H), 2.82 - 2.71 (m, 1H), 2.32 (s, 3H) |
1.359 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2-1,3-苯并㗁唑基- | 1 H NMR (400 MHz, d6-DMSO), δ ppm 10.81 (s,1H), 7.65 - 7.57 (m, 3H), 7.36 - 7.30 (m, 2H), 7.28 - 7.23 (t,1H), 3.53 (s, 3H), 3.09 - 2.99 (m, 4H), 2.19 (s, 3H) |
1.360 | -Me | -Me | -H | 6-F | 3-Cl | -CH2 -CH2 - | 2-1,3-苯并噻唑基 | 1 H NMR (400 MHz, DMSO-D6) δ ppm 10.85 (br. s,1H), 8.04 - 8.02 (d, 1H), 7.91 - 7.89 (d, 1H), 7.61 - 7.58 (dd, 1H), 7.49 - 7.46 (t, 1H), 7.41 - 7.37 (t, 1H), 7.28 - 7.23 (t, 1H), 3.57 (s, 3H), 3.26 - 3.13 (m, 2H), 3.07 - 2.92 (m, 2H), 2.21 (s, 3H) |
2.362 | -Me | -Me | -H | 6-F | 3-Cl | (E)-CH=CH- | 6-2,2-二甲基-3H-苯并呋喃基- | 1 H NMR (400 MHz, 甲醇) 7.52 (dd, J=5.1, 8.8 Hz,1H), 7.12 (t, J=8.8Hz, 1H), 7.05 (d, J=7.6 Hz, 1H), 6.91 (d, J=16.4 Hz, 1H), 6.70 (dd, J=1.3, 7.6 Hz, 1H), 6.62 (s, 1H), 6.47 (d, J=16.4 Hz, 1H), 3.66 (s, 3H), 2.97 (s, 2H), 2.26 (s, 3H), 1.42 (s, 6H) |
2.363 | -Me | -Me | -H | 6-F | 3-Cl | (E)-CH=CH- | 6-咪唑并[1,2-a]吡𠯤基- | 1 H NMR (400 MHz, DMSO-d6) 10.83 (br. s,1H), 9.06 (s, 1H), 8.55 (d, J=1.1 Hz, 1H), 8.07 (s, 1H), 7.79 (d, J=1.1 Hz, 1H), 7.63 (dd, J=5.3, 8.8 Hz, 1H), 7.48 (d, J=15.9 Hz, 1H), 7.28 (t, J=8.8 Hz, 1H), 6.65 (d, J=15.9 Hz, 1H), 3.56 (s, 3H), 2.20 (s, 3H) |
4.342 | -Me | -Me | -(C=O)iPr | 6-F | 3-Cl | (E)-CH=CH- | 2,2-二氟-5-1,3-苯并間二氧雜環戊烯基- | 1 H NMR (400 MHz, 氯仿) δ = 7.43 (dd, J = 5.1, 8.9 Hz, 1H), 7.12 (d, J = 1.6 Hz, 1H), 7.05 - 6.95 (m, 3H), 6.91 (d, J = 16.5 Hz, 1H), 6.60 (d, J = 16.5 Hz, 1H), 3.71 (s, 3H), 2.64 (spt, J = 7.0 Hz, 1H), 2.23 (s, 3H), 1.10 (d, J = 7.0 Hz, 3H), 1.07 (d, J = 7.0 Hz, 3H) |
生物學實施例
B1
出苗後功效
-
測試
1
將以下多種測試物種的種子播種在盆中的標準土壤中:- 龍葵(Solanum nigrum
)(SOLNI)、反枝莧(Amaranthus retoflexus
)(AMARE)、大狗尾草(Setaria faberi
)(SETFA)、稗草(Echinochloa crus-galli
)(ECHCG)、碗仔花(Ipomoea hederacea
)(IPOHE)、多年生黑麥草(Lolium perenne
)(LOLPE)。在溫室中在受控條件(在24°C/16°C白天/夜晚下;14小時光照;65%濕度)下培養八天後(出苗後),用水性噴霧溶液噴灑該等植物,該水性噴霧溶液源自工業級活性成分在丙酮/水(50 : 50)溶液中的配製物,該溶液含有0.5%吐溫(Tween)20(聚氧乙烯脫水山梨糖醇單月桂酸酯,CAS RN 9005-64-5)。以250 g/ha施用化合物。然後使測試植物在溫室中在受控條件(在24°C/16°C白天/夜晚下;14小時光照;65%濕度)下生長,並且每日澆水兩次。在13天之後,對該測試給植物造成的損害百分比進行評價。以五分制評估生物活性(5
= 80%-100%;4
= 60%-79%;3
= 40%-59%;2
= 20%-39%;1
= 0-19%)。在表中的空白值表明那種化合物未在那種物種上進行測試。
[
表
6]
出苗後施用後具有式
(I)
之化合物對雜草物種的控制
化合物 | AMARE | SOLNI | SETFA | LOLPE | ECHCG | IPOHE |
1.019 | 4 | 5 | 5 | 5 | 3 | 5 |
1.027 | 2 | 4 | 4 | 4 | 5 | |
1.028 | 5 | 5 | 5 | 5 | 5 | 5 |
1.036 | 5 | 5 | 5 | 5 | 5 | 5 |
2.034 | 1 | 5 | 2 | 2 | 3 | |
3.030 | 5 | 5 | 5 | 5 | 5 | 5 |
3.034 | 4 | 5 | 5 | 5 | 4 | 4 |
4.034 | 1 | 5 | 2 | 1 | 3 | |
1.357 | 5 | 5 | 5 | 5 | 4 | 5 |
4.342 | 0 | 4 | 1 | 2 | 1 | 3 |
B2
出苗後功效
-
測試
2
將以下多種測試物種的種子播種在盆中的標準土壤中:- 反枝莧(Amaranthus retoflexus
)(AMARE)、大狗尾草(Setaria faberi
)(SETFA)、稗草(Echinochloa crus-galli
)(ECHCG)、碗仔花(Ipomoea hederacea
)(IPOHE)、玉蜀黍(Zea Mays
)(ZEAMX)、苘麻(Abutilon theophrasti
)(ABUTH)。在溫室中在受控條件(在24°C/16°C白天/夜晚下;14小時光照;65%濕度)下培養八天後(出苗後),用水性噴霧溶液噴灑該等植物,該水性噴霧溶液源自工業級活性成分在丙酮/水(50 : 50)溶液中的配製物,該溶液含有0.5%吐溫20(聚氧乙烯脫水山梨糖醇單月桂酸酯,CAS RN 9005-64-5)。以250 g/ha施用化合物。然後使測試植物在溫室中在受控條件(在24°C/16°C白天/夜晚下;14小時光照;65%濕度)下生長,並且每日澆水兩次。在13天之後,對該測試給植物造成的損害百分比進行評價。以五分制評估生物活性(5
= 80%-100%;4
= 60%-79%;3
= 40%-59%;2
= 20%-39%;1
= 0-19%)。在表中的空白值表明那種化合物未在那種物種上進行測試。
[
表
7]
出苗後施用後具有式
(I)
之化合物對雜草物種的控制
化合物 | AMARE | ZEAMX | SETFA | ABUTH | ECHCG | IPOHE |
1.339 | 4 | 0 | 4 | 3 | 5 | 4 |
1.340 | 5 | 5 | 5 | 5 | 5 | 4 |
1.341 | 5 | 4 | 4 | 5 | 5 | 5 |
1.342 | 5 | 4 | 4 | 5 | 5 | 5 |
1.318 | 4 | 2 | 5 | 4 | 4 | 4 |
1.344 | 3 | 1 | 4 | 2 | 3 | |
1.345 | 4 | 2 | 4 | 4 | 3 | 4 |
1.346 | 2 | 2 | 0 | 4 | 4 | 3 |
1.347 | 4 | 4 | 4 | 4 | 4 | 4 |
1.348 | 4 | 4 | 4 | 3 | 4 | 4 |
1.349 | 4 | 2 | 4 | 4 | 4 | 4 |
1.350 | 4 | 3 | 4 | 5 | 4 | 3 |
1.351 | 5 | 5 | 4 | 5 | 4 | 5 |
1.352 | 4 | 3 | 4 | 4 | 4 | 3 |
1.353 | 4 | 3 | 4 | 4 | 4 | 3 |
1.354 | 4 | 4 | 4 | 4 | 5 | 4 |
1.355 | 4 | 1 | 2 | 3 | 1 | 4 |
1.356 | 5 | 2 | 5 | 4 | 4 | 4 |
1.044 | 3 | 1 | 0 | 3 | 0 | 4 |
1.053 | 4 | 4 | 4 | 3 | 3 | 4 |
1.357 | 2 | 5 | 4 | 4 | 4 | |
1.359 | 3 | 1 | 3 | 4 | 3 | 2 |
1.361 | 3 | 4 | 5 | 5 | 4 | 5 |
2.363 | 1 | 0 | 0 | 0 | 0 | 2 |
B3
出苗前功效
-
測試
1
將以下多種測試物種的種子播種在盆中的標準土壤中:龍葵(Solanum nigrum
)(SOLNI)、反枝莧(Amaranthus retoflexus
)(AMARE)、大狗尾草(Setaria faberi
)(SETFA)、稗草(Echinochloa crus-galli
)(ECHCG)、碗仔花(Ipomoea hederacea
)(IPOHE)、多年生黑麥草(Lolium perenne
)(LOLPE)。在溫室中在受控條件(在24°C/16°C白天/夜晚下;14小時光照;65%濕度)下培養一天之後(出苗前),用水性噴霧溶液噴灑該等植物,該水性噴霧溶液源自工業級活性成分在丙酮/水(50 : 50)溶液中的配製物,該溶液含有0.5%吐溫20(聚氧乙烯脫水山梨糖醇單月桂酸酯,CAS RN 9005-64-5)。以250 g/ha施用化合物。然後使測試植物在受控制的條件(在24°C/16°C白天/夜晚下;14小時光照;65%濕度)下生長於溫室中,並且每天澆水兩次。在13天之後,對該測試給植物造成的損害百分比進行評價。以五分制評估生物活性(5
= 80%-100%;4
= 60%-79%;3
= 40%-59%;2
= 20%-39%;1
= 0-19%)。在表中的空白值表明那種化合物未在那種物種上進行測試。
[
表
8]
在出苗前施用之後具有式
(I)
之化合物對雜草物種的控制
化合物 | AMARE | SOLNI | SETFA | LOLPE | ECHCG | IPOHE |
1.019 | 5 | 5 | 4 | 3 | 1 | 1 |
1.027 | 1 | 4 | 1 | 3 | 3 | 3 |
1.028 | 5 | 5 | 5 | 5 | 1 | 5 |
1.036 | 5 | 5 | 5 | 5 | 5 | 5 |
2.034 | 1 | 2 | 1 | 1 | 1 | 0 |
3.030 | 5 | 5 | 5 | 5 | 5 | 5 |
3.034 | 5 | 5 | 5 | 5 | 5 | 2 |
4.034 | 0 | 1 | 0 | 0 | 0 | 0 |
4.342 | 1 | 3 | 0 | 0 | 0 | 1 |
B4
出苗前功效
-
測試
2
將以下多種測試物種的種子播種在盆中的標準土壤中:反枝莧(Amaranthus retoflexus
)(AMARE)、大狗尾草(Setaria faberi
)(SETFA)、稗草(Echinochloa crus-galli
)(ECHCG)、碗仔花(Ipomoea hederacea
)(IPOHE)、玉蜀黍(Zea Mays
)(ZEAMX)、苘麻(Abutilon theophrasti
)(ABUTH)。在溫室中在受控條件(在24°C/16°C白天/夜晚下;14小時光照;65%濕度)下培養一天之後(出苗前),用水性噴霧溶液噴灑該等植物,該水性噴霧溶液源自工業級活性成分在丙酮/水(50 : 50)溶液中的配製物,該溶液含有0.5%吐溫20(聚氧乙烯脫水山梨糖醇單月桂酸酯,CAS RN 9005-64-5)。以250 g/ha施用化合物。然後使測試植物在受控制的條件(在24°C/16°C白天/夜晚下;14小時光照;65%濕度)下生長於溫室中,並且每天澆水兩次。在13天之後,對該測試給植物造成的損害百分比進行評價。以五分制評估生物活性(5
= 80%-100%;4
= 60%-79%;3
= 40%-59%;2
= 20%-39%;1
= 0-19%)。在表中的空白值表明那種化合物未在那種物種上進行測試。
[
表
9]
在出苗前施用之後具有式
(I)
之化合物對雜草物種的控制
化合物 | AMARE | ZEAMX | SETFA | ABUTH | ECHCG | IPOHE |
1.339 | 5 | 1 | 5 | 4 | 5 | 2 |
1.340 | 5 | 3 | 5 | 5 | 5 | 5 |
1.341 | 5 | 4 | 5 | 5 | 5 | 5 |
1.342 | 5 | 1 | 5 | 4 | 5 | |
1.318 | 5 | 2 | 5 | 3 | 5 | 4 |
1.344 | 3 | 0 | 2 | 4 | 2 | 3 |
1.345 | 5 | 1 | 5 | 4 | 2 | 5 |
1.346 | 3 | 1 | 0 | 4 | 0 | 3 |
1.347 | 5 | 3 | 3 | 5 | 2 | 5 |
1.348 | 5 | 1 | 3 | 3 | 4 | 5 |
1.349 | 5 | 4 | 5 | 4 | 5 | 5 |
1.350 | 5 | 4 | 5 | 5 | 5 | 5 |
1.351 | 5 | 5 | 5 | 5 | 5 | 5 |
1.352 | 5 | 4 | 5 | 4 | 3 | 3 |
1.353 | 5 | 4 | 5 | 4 | 5 | 5 |
1.354 | 4 | 4 | 5 | 4 | 5 | 5 |
1.355 | 3 | 1 | 1 | 0 | 0 | 2 |
1.356 | 3 | 0 | 1 | 1 | 1 | 2 |
1.044 | 2 | 1 | 0 | 3 | 0 | 3 |
1.053 | 4 | 1 | 2 | 2 | 2 | 1 |
1.357 | 4 | 1 | 4 | 4 | 4 | 3 |
1.359 | 5 | 3 | 5 | 5 | 5 | 4 |
1.361 | 4 | 1 | 5 | 5 | 3 | 4 |
2.363 | 5 | 2 | 4 | 5 | 5 | 5 |
1.339 | 1 | 0 | 1 | 0 | 1 | 0 |
無
無
Claims (20)
- 一種具有式 (I) 之化合物,(I), 或其鹽或N-氧化物,其中, R1 選自由以下組成之群組:C1 -C4 烷基、C3 -C6 環烷基、C3 -C6 烷氧基、C1 -C2 烷氧基-C1 -C2 烷基-、C2 -C4 烯基、C1 -C4 鹵代烷基、氰基-C1 -C4 烷基、C2 -C4 鹵代烯基、C2 -C4 炔基和C2 -C4 鹵代炔基; R2 選自由以下組成之群組:氫、鹵素、氰基、C1 -C6 烷基、C1 -C6 鹵代烷基、C1 -C6 鹵代烷氧基、C1 -C3 鹵代烷氧基-C1 -C3 烷基-、C1 -C6 烷氧基、C1 -C3 烷氧基-C1 -C3 烷基、C1 -C3 烷氧基-C1 -C3 烷氧基-C1 -C3 烷基-、C3 -C6 環烷基、C2 -C6 烯基、C2 -C6 鹵代烯基、C2 -C6 炔基、C1 -C6 羥基烷基-、C1 -C6 烷基羰基-、-S(O)m C1 -C6 烷基、胺基、C1 -C6 烷基胺基、C1 -C6 二烷基胺基、-C(C1 -C3 烷基)=N-O-C1 -C3 烷基和C2 -C6 鹵代炔基; G係氫、或C(O)R3 ; R3 選自由以下組成之群組:C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基、C1 -C6 烷基-S-、C1 -C6 烷氧基、-NR4 R5 和視需要被一個或多個R6 取代的苯基; R4 和R5 各自獨立地選自由以下組成之群組:氫、C1 -C6 烷基、C1 -C6 烷氧基和C3 -C6 環烷基,或者R4 和R5 一起可以形成𠰌啉基環;並且, R6 選自由以下組成之群組:鹵素、氰基、硝基、C1 -C3 烷基、C1 -C3 鹵代烷基、C1 -C3 烷氧基以及C1 -C3 鹵代烷氧基; X和Y各自獨立地是氫、C1 -C3 烷基、環丙基、C1 -C3 烷氧基、C1 -C3 鹵代烷基、C1 -C3 鹵代烷氧基、或鹵素; D係經取代或未經取代的萘環系統,或包含1、2、3或4個獨立地選自氧、氮和硫的雜原子的經取代或未經取代的8-10員二環飽和、部分飽和或不飽和的雜環系統,並且其中當D被取代時,其在至少一個環碳原子上被R8 取代和/或在至少一個環氮原子上被R9 取代; 每個R8 獨立地是氧、羥基、鹵素、氰基、C1 -C6 烷基、C1 -C6 鹵代烷基、C3 -C6 -環烷基、C1 -C6 烷氧基、C1 -C6 鹵代烷氧基、C1 -C3 烷氧基-C1 -C3 烷基、C1 -C3 鹵代烷氧基-C1 -C3 烷基-、C1 -C3 烷氧基-C1 -C3 烷氧基-C1 -C3 烷基-、C2 -C6 烯基、C2 -C6 鹵代烯基、C2 -C6 炔基、C2 -C6 鹵代炔基、C1 -C6 羥基烷基-、C1 -C6 烷基羰基-、C1 -C6 鹵代烷基羰基-、C3 -C6 環烷基羰基-、C1 -C6 烷基-S(O)m -、-S(O)m -C1 -C6 鹵代烷基、-S(O)m -C3 -C6 環烷基、-O-S(O)2 C1 -C3 烷基、-C1 -C3 烷基-S(O)m -C1 -C6 烷基、-C1 -C3 烷基-S(O)m -C1 -C6 鹵代烷基、-C1 -C3 烷基-S(O)m -C3 -C6 環烷基、氰基-C1 -C6 -烷基-、-NR4 R5 、-C(C1 -C3 烷基)=N-O-C1 -C3 烷基、-C(S)NH2 、C1 -C6 烷基胺基硫代羰基-、二(C1 -C6 烷基)胺基硫代羰基-、C3 -C6 -環烷基胺基-硫代羰基-S(O)2 NH2 、-S(O)2 NHC(O)C1 -C3 烷基、C1 -C6 烷基胺基磺醯基-、二(C1 -C6 烷基)胺基磺醯基-、C3 -C6 -環烷基胺基-磺醯基-、-C(O)OH、-C(O)OC1 -C6 烷基、-C(O)NHS-(O)2 C1 -C6 烷基、-C(O)NR4 R5 、-NR4 C(O)NR4 R5 、C1 -C6 烷基羰基(C1 -C6 烷基)胺基-、C1 -C6 鹵代烷基羰基胺基-、C1 -C6 鹵代烷基羰基(C1 -C6 烷基)胺基-、C1 -C6 烷氧基羰基胺基-、C1 -C6 烷氧基羰基(C1 -C6 烷基)胺基-、C1 -C6 烷基磺醯基胺基-、C1 -C6 烷基磺醯基(C1 -C6 烷基)胺基-、C1 -C6 鹵代烷基磺醯基胺基-、C1 -C6 鹵代烷基磺醯基(C1 -C6 烷基)胺基-、C3 -C6 環烷基磺醯基胺基-、C3 -C6 環烷基磺醯基(C1 -C6 烷基)胺基-、C1 -C6 烷基胺基羰基胺基-、C1 -C6 烷基胺基羰基(C1 -C6 烷基)胺基、二(C1 -C6 烷基)胺基羰基胺基-、C1 -C6 鹵代烷基胺基羰基胺基-、C1 -C6 鹵代烷基胺基羰基(C1 -C6 烷基)胺基、二(C1 -C6 鹵代烷基)胺基羰基胺基-、二(C1 -C6 鹵代烷基)胺基羰基(C1 -C6 烷基)胺基-、羥基胺基-、羥基(C1 -C6 烷基)胺基、C1 -C6 烷氧基胺基、C1 -C6 烷氧基(C1 -C6 烷基)胺基、C1 -C6 鹵代烷氧基胺基、C1 -C6 鹵代烷氧基(C1 -C6 烷基)胺基、或選自由苯基環、5-6員雜芳基環和3-6員雜環基環組成的組的環系統,其中所述環系統被0至5個R16 取代; m係0、1或2的整數; 每個R9 獨立地是C1 -C6 烷基、C1 -C6 鹵代烷基、羥基、C1 -C4 烷氧基、C1 -C4 烷硫基、C3 -C6 -環烷基、C1 -C3 烷氧基-C1 -C3 烷基、C1 -C3 鹵代烷氧基-C1 -C3 烷基-、C1 -C3 烷氧基-C1 -C3 烷氧基-C1 -C3 烷基-、C1 -C6 羥基烷基-、-C1 -C3 烷基-S(O)m -C1 -C6 烷基、-C1 -C3 烷基-S(O)m -C1 -C6 鹵代烷基、-C1 -C3 烷基-S(O)m -C3 -C6 環烷基、氰基-C1 -C6 -烷基-、或選自由苯基環、5-6員雜芳基環和3-6員雜環基環組成之群組的環系統,其中所述環系統被0至5個R16 取代; 每個R16 獨立地是鹵素、氰基、C1 -C6 烷基、C1 -C6 鹵代烷基、C1 -C6 烷氧基或C1 -C6 鹵代烷氧基;並且, W係W1或W2、或W3, 其中 「a」表示與苯基-嗒𠯤酮/苯基-嗒𠯤二酮部分的附接點, 「b」表示與環D的附接點, R10 、R12 、R14 和R15 各自獨立地是氫、C1 -C3 烷基或C1 -C3 鹵代烷基;或者R10 和R12 與它們所連接的碳原子一起形成C3 -C6 碳環;並且 R11 和R13 各自獨立地是氫、鹵素、C1 -C3 烷基、或C1 -C3 鹵代烷基,其前提係當R11 或R13 之一係鹵素、C1 -C3 烷基或C1 -C3 鹵代烷基時,另一個係氫。
- 如請求項1所述之化合物,其中,G係氫或C(O)R3 ,其中R3 係異丙基、三級丁基、甲基、乙基、炔丙基、甲氧基、乙氧基、或三級丁氧基。
- 根據前述請求項中任一項所述之化合物,其中,X係氫、鹵素、或C1 鹵代烷基。
- 根據前述請求項中任一項所述之化合物,其中,Y係氫、C1 -C3 烷基、環丙基、C1 -C3 鹵代烷基、或鹵素。
- 如前述請求項中任一項所述之化合物,其中,相對於該嗒𠯤酮/嗒𠯤-二酮部分,X係在鄰位。
- 如前述請求項中任一項所述之化合物,其中,相對於-W-D部分,Y係在鄰位。
- 如前述請求項中任一項所述之化合物,其中,R1 係甲基、乙基、正丙基、環丙基、炔丙基或C1 鹵代烷基。
- 如前述請求項中任一項所述之化合物,其中,R2 選自由以下組成之群組:氫、鹵素、C1 -C6 烷基、C1 -C6 鹵代烷基、C1 -C6 烷氧基、C1 -C3 烷氧基-C1 -C3 烷基、C3 -C6 環烷基、C2 -C6 烯基、C2 -C6 鹵代烯基、C2 -C6 炔基和C2 -C6 鹵代炔基。
- 如前述請求項中任一項所述之化合物,其中,D係經取代或未經取代的萘、吲口巾、吲哚、異吲哚、吲哚啉、異吲哚啉、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并㗁唑、苯并間二氧雜環戊烯、嘌呤、4H-喹口巾、喹啉、異喹啉、四氫喹啉、口辛啉、酞𠯤、喹㗁啉、1-8-口奈啶、喋啶、1H-吡咯并[2,3-b]吡啶、咪唑并[1,2-a]吡𠯤或1H-苯并三唑環系統,並且其中當D被取代時,其在至少一個環碳原子上被R8 取代和/或在至少一個環氮原子上被R9 取代。
- 如前述請求項中任一項所述之化合物,其中,D係經取代或未經取代的萘、吲口巾、吲哚、異吲哚、3-H-吲哚、苯并呋喃、苯并噻吩、1H-吲唑、苯并咪唑、苯并噻唑、苯并㗁唑、嘌呤、4H-喹口巾、喹啉、異喹啉、四氫喹啉、口辛啉、酞𠯤、喹㗁啉、1-8-口奈啶、或喋啶環系統,並且其中當D被取代時,其在至少一個環碳原子上被R8 取代和/或在至少一個環氮原子上被R9 取代。
- 如前述請求項中任一項所述之化合物,其中,每個R8 獨立地是氧、羥基、鹵素、氰基、C1 -C6 烷基、C1 -C6 鹵代烷基、C1 -C6 鹵代烷氧基、C1 -C3 鹵代烷氧基-C1 -C3 烷基-、C1 -C6 烷氧基、C1 -C3 烷氧基-C1 -C3 烷基、C1 -C3 烷氧基-C1 -C3 烷氧基-C1 -C3 烷基-、C3 -C6 環烷基、C2 -C6 烯基、C2 -C6 鹵代烯基、C2 -C6 炔基、C1 -C6 羥基烷基-、C1 -C6 烷基羰基-、C1 -C6 烷基-S(O)m -、胺基、C1 -C6 烷基胺基、C1 -C6 二烷基胺基、-C(C1 -C3 烷基)=N-O-C1 -C3 烷基或C2 -C6 鹵代炔基。
- 如前述請求項中任一項所述之化合物,其中,每個R9 獨立地是C1 -C4 烷基、C1 -C4 鹵代烷基、羥基、C1 -C4 烷氧基、或C1 -C4 烷硫基。
- 如前述請求項中任一項所述之化合物,其中,W係W1並且R10 、R11 、R12 和R13 各自係氫。
- 如請求項1至12中任一項所述之化合物,其中,W係W2並且R14 和R15 各自係氫。
- 一種除草組成物,其包含如請求項1-15中任一項所述之除草化合物、和農業上可接受的配製佐劑。
- 如請求項16所述之除草組成物,其進一步包含至少一種額外的殺有害生物劑。
- 如請求項17所述之除草組成物,其中,該額外的殺有害生物劑係除草劑或除草劑安全劑。
- 一種控制不想要的植物生長之方法,該方法包括將如請求項1至15中任一項所定義的具有式 (I) 之化合物或如請求項16至18中任一項所述之除草組成物施用至不想要的植物或其場所。
- 一種如請求項1至15中任一項所定義的具有式 (I) 之化合物之用途,其作為除草劑。
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ZA202109504B (en) | 2022-09-28 |
UY38788A (es) | 2021-02-26 |
KR20220035372A (ko) | 2022-03-22 |
EP3999503C0 (en) | 2024-04-03 |
AU2020313369A1 (en) | 2022-01-27 |
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