TW200526672A - Chemical compounds - Google Patents
Chemical compounds Download PDFInfo
- Publication number
- TW200526672A TW200526672A TW093126017A TW93126017A TW200526672A TW 200526672 A TW200526672 A TW 200526672A TW 093126017 A TW093126017 A TW 093126017A TW 93126017 A TW93126017 A TW 93126017A TW 200526672 A TW200526672 A TW 200526672A
- Authority
- TW
- Taiwan
- Prior art keywords
- me3si
- cf2h
- formula
- optionally substituted
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 208
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 60
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004480 active ingredient Substances 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004429 atom Chemical group 0.000 claims abstract description 8
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 4
- 244000005700 microbiome Species 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract 2
- 150000001204 N-oxides Chemical class 0.000 claims abstract 2
- -1 methyl amidino Chemical group 0.000 claims description 76
- 239000000460 chlorine Substances 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000004575 stone Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 238000002360 preparation method Methods 0.000 abstract description 14
- 125000005282 allenyl group Chemical group 0.000 abstract description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 9
- 239000000543 intermediate Substances 0.000 abstract description 5
- 241000233866 Fungi Species 0.000 abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 230000000855 fungicidal effect Effects 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 206010061217 Infestation Diseases 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 238000003898 horticulture Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 241000196324 Embryophyta Species 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- 238000012360 testing method Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 19
- WANLLPADDCXPGO-WMKJBNATSA-N (6r,9s,12s)-3-[(2s)-butan-2-yl]-6-[(4-methoxyphenyl)methyl]-9-[6-(oxiran-2-yl)-6-oxohexyl]-1,4,7,10-tetrazabicyclo[10.4.0]hexadecane-2,5,8,11-tetrone Chemical compound C([C@@H]1C(=O)NC(C(N2CCCC[C@H]2C(=O)N[C@@H](CCCCCC(=O)C2OC2)C(=O)N1)=O)[C@@H](C)CC)C1=CC=C(OC)C=C1 WANLLPADDCXPGO-WMKJBNATSA-N 0.000 description 14
- WANLLPADDCXPGO-UHFFFAOYSA-N Cyl-2 Natural products N1C(=O)C(CCCCCC(=O)C2OC2)NC(=O)C2CCCCN2C(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(OC)C=C1 WANLLPADDCXPGO-UHFFFAOYSA-N 0.000 description 14
- 108010063406 Cyl-2 Proteins 0.000 description 14
- 101100112677 Mus musculus Ccnd3 gene Proteins 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 239000003480 eluent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 235000013399 edible fruits Nutrition 0.000 description 9
- 208000015181 infectious disease Diseases 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 6
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 6
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 238000004891 communication Methods 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 244000070406 Malus silvestris Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 239000005745 Captan Substances 0.000 description 2
- 241001432959 Chernes Species 0.000 description 2
- 235000002787 Coriandrum sativum Nutrition 0.000 description 2
- 244000018436 Coriandrum sativum Species 0.000 description 2
- 241000219112 Cucumis Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 239000006002 Pepper Substances 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 239000012872 agrochemical composition Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229940117949 captan Drugs 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 210000004268 dentin Anatomy 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- IGUYEXXAGBDLLX-UHFFFAOYSA-N ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-1,3-oxazolidine-5-carboxylate Chemical compound O=C1C(C(=O)OCC)(C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 IGUYEXXAGBDLLX-UHFFFAOYSA-N 0.000 description 2
- JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 125000005630 sialyl group Chemical group 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005533 tritiation Methods 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical group [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
200526672 九、發明說明: 【發明所屬之技術領域】 本‘明仏有關於一種新穎的含矽醯胺衍生物,其具有 殺微生物活性,特別是殺真菌活性。本發明亦有關於二種 使用於製備這些化合物的新穎中間體,一種包含至少其中 :種新穎化合物做為活性成分的農化組成物,及一種將該 寺活性成分或組成物在農業或園藝中使用為控制或防止植 物文植物病原微生物,較佳為真菌,感染的用途。 【先前技術】 一些苯基醯胺和暖吩醯胺,其等係經將於下文中特別 述及之έ石夕取代基取代,已揭示於9。 【發明内容】 本發明係提供一種式(I)化合物··
其中X為Ο或S ,· RING為苯基或_吩基;Het為含有 至二個雜原子係個別獨立地選自氧、氮和硫的5 _或6-員 錶環,該環經一至四個R4基取代;R1為氫,選擇性經取代 之(Cl·4)烷基,甲醯基,選擇性經取代之烷基C卜⑺, 4擇丨生經取代之((^_4)烧基C(=〇)〇,選擇性經取代之(q 4) ^氧基(CN4)烷基,選擇性經取代之烯丙基,選擇性經取代 7 200526672 之块^基或選擇性經取代之丙二婦基;每個r2獨立地為虐 素乙擇性玺取代之(c!_4)烧基,選擇性經取代之(c丨_4)燒氧 基f f擇性經取代之(CM烷氧基(Ci4)烷基;r3為 (CR R )m-Cy_(CRCRd)n_Y ;每個r4獨立地選自齒素,[Μ炫 基,齒烷基,CN3烷氧基(C,_3)烷基和氰基;Ra,Rb, R和R A別獨立地為氫或選擇性經取代之U烧基;Cy 為選擇性經取代之碳賴或料狀3_7貞環且可為飽和、不 飽和或芳香性並選擇性地含有石夕原子做為環員;(cm 和(C^)n可與〇内之相同的碳或石夕原子鍵結,或經卜2 或3員環分離的不同原子鍵結;γ為s w)(q/)(⑽, 唯其:艮制為當^含有矽原子為環員時則Y亦可為氫;Z為 c,-4烧基或c2_4埽基(每個均可選擇性地經一個選自〇、s和 N的雜原子插人並可選擇性地經—至三個獨立選自函素之 ^取代及Z2獨立地為甲基或乙基;個別獨立 0 ’ 1 ’ 2或3 ; ρ ’ # s個別獨立地為〇或及『為 ’ 1或2,或為它的N•氧化物,唯其限制為當一均為 〇且RING^cy均為苯基時YJt非為三%•收基甲梦烧基。 I、為亂飞,溴或碘,較佳為氟,氯或溴。 母個炫基部分為分枝或未分枝且例如為甲基,乙基, 丙基’ML異丙基’第二丁基’異· 丁基或第三丁 每個烯基部分為分枝或未分枝。 每個烯基部㈣當地為㈤_或迎構形。 田心基4刀、埽丙基、块丙基和丙二稀基存有個別選 200526672 擇性取代基時,可獨立地選自齒素,經基,氛基基, 甲乳基碳基,乙氧基幾基’甲氧基,乙氧基,甲基錯醯基, 乙基石黃醯基,二氟甲氧基,三敦甲氧基和三氣甲基硫基; 在發明的另一個範圍中,當烧基部分、烯丙基、块丙基和 丙二烯基存有個別選擇性取代基時,可獨立地選自函素, 羥基,氰基,敌基,甲氧基幾基,乙氧基幾基,甲氧基, 乙氧基,甲基確醯基,乙基姐基,二氟 氧基和三氟硫基甲氧基。 一乳τ 當在cy #有個別選擇性取代基時,可獨立地選自齒 :,(C,-4)燒基,(C2-4)婦基’ (c]-4)齒燒基,(Cl屬氧基和 鹵(Cl-4)烷氧基。 較佳之X為氧。 較佳者為,f『RING』為噻吩基時,貝4 N(R,)cxHet 基接在位置3。 較佳者為Het為®唾基’毗咯基,硫笨基,呋喃基,噬 唑基’異噻唑基,噁唑基’異噁唑基,三唑基,毗啶基, 毗嗪基’嘧啶基,噠嗪基,5,6-二氫D比喃基或5,m,4_ 氧硫雜環己二烯基(更佳為心基,㈣基,硫笨基,肤喃 基’唑基’噁唑基,U3-三唑基’吡啶基,嘧啶基,噠 嗪基5,6-二氫卩比喃基或5,6·二氫-I,4-氧硫雜環己二烯基; 最佳為毗唑基,毗咯基,噻唑基,丨,2,3-三唑基或毗啶基), 個別地經一至三個R4基取代且經由碳原子與C( = x)_N(Ri) 基相連接。 曱醯基, 較it者為為氫,快丙基,丙二稀義, 9 200526672 CH3c(=0),c2H5C(=〇)或 CH3〇CH2C(=〇);更佳為氫炔内 基,丙二烯基,曱醯基,CH3C(=〇)或C2H5C(=0)。 最佳為R1為氫。 車乂佺者為R2獨立地選自鹵素,甲基,三氟甲基和三氟 甲氧基。 較佳者為R4獨立地選自自素,甲基,CF3,CF2H,CH2F, CF2C1 和 ch2〇CH3。 較佳者為在Het環中並未與它們的鄰近原子藉由雙鍵 連接的氮原子係個別獨立地未經取代或經R4取代(更佳為 它們個別獨立地經R4取代);其中每個R4獨立地選自Ch 烷基,Cw鹵烷基和曱氧基亞甲基;更佳地係選自C12燒3 基,CF3, CFK卜CHF2, CHJ和甲氧基亞甲基;甚至更佳 地係選自甲基,CHF2和甲氧基亞f S ;及最佳為甲基。 較佳者為在Het環中並未與經c(=x)_N(Rl)基取代的原 子鍵結的碳原子係個別獨立地未經取代或經R4取代;其中 每個R4獨立地選自齒素’ C丨·3烧基’ c“3論烷基和甲氧基 亞甲基;更佳地係選自氯,甲氧基亞甲基,CF3, CHF2和 CF3 ;甚至更佳地係選自CH3,CHF2和CF3。 其中會有一或兩個在Het環中與經c(=x)_N(Ri)基取代 的原子鍵結,較佳為這些碳原子的其中—個經R4取代;其 係獨立地選自鹵素,C, -3烷基和c ] 3鹵烷基;更佳地係選自 氯’氟,溴’ C】.2烧基,CF3 ’ CF2n,CHF2和CH2f ;甚至 更佳地係選自氯,氟,溴,曱基,Cp3,CHF2和CH2F。若 存有與經CXNR1基取代的原子鍵結的第二個碳原子時,其 200526672 或經r4取代;其係獨立 為選自氟和氯。 地選自 鹵素;更佳 接…*佳者為(CRaRb)m-Cy-(CRCR〜-Y與『觸』相 的石^位於與攜有N(Rl)c(=x)Het基的碳相鄰(鄰位)。 者為R,Rb,RC和Rd個別獨立地為氫或甲基,最 當Cy為矽雜環時〔亦即其含有矽原子做為環員〕,較 。,為〇或1 (更佳為0),η為1或2(更佳為1)且γ為氫。 田Cy非為石夕雜環時,較佳為m為〇或^(更佳為 〇 為0,1或2。 車乂佺者為Cy為飽和的3-7員碳環且選擇性地經至多4 们取代基取代(較佳為個別取代基獨立地選自cU4烷基;更 :為:別為甲基),含有-個雙鍵的5_7員碳環且選擇性地 、、二至夕4個取代基取代(較佳為個別取代基獨立地選自Cy ^基,更佳為個別為曱基),飽和或未飽和的4-7員矽雜環 且選擇性地經至多4個取代基取代(較佳為個別取代基獨立 地選自Cw烷基;(:24烯基和Ci.4烷氧基;更佳為選自甲基, 乙基,丙基,異丙基,烯丙基,乙烯基,甲氧基和乙氧基) 或Cy為苯基,硫苯基,呋喃或吡啶基且選擇性地經至多4 個取代基取代(其較佳為個別為il素,曱基,曱氧基或三氟 曱氣基)。 更佳者為Cy係選自下列的環: 200526672
Cy20 Cy21 Cy22
b
Cy卜 Cy2,Cy4,Cy5,Cy7,Cy8,Cyl 卜 Cyl2,Cyl3,
Cyl6,Cy20,Cy21和Cy22的對稱性質意為那一個箭頭表 不與(CRaRb)m部分的鍵結及那一個箭頭表示與(CRCRd)n部 分的鍵結並沒有關係。但是Cy3,Cy6, Cy9,Cyi(),^4, Ο15 和Cy24並不具對稱性因 此那一個前頭表示盘部八 干愈咖… 的鍵結及那-個箭頭表 二右『 的鍵結即有所關係;對於此較佳
广㈣頭係表示與(CRaR 標不有『b』的箭頭係表示與 璲、口〔因而 說明書中,Cy3a係A ” n 一分的鍵結〕。於此 ”中箭頭a』代表與(cw)m部分鍵 12 200526672
同時Cy3b係為其中箭頭 b』代表與(CReRd) 可依所需變化地應用至Cy6, 相间地,可依所需變化地應用至 ⑽,Cyl7, Cyl8, Cvl9, 較佳者為ζι為甲基。 較佳者為Z2為甲基。 較佳者為z為Ck4烷基 ,Cyl8,Cyl9,Cy23 和 』基較佳為相對應至『b』基。 ,更佳為甲基。 較佳者為P為〇。 較佳者為q為0。 較佳者為!*為〇或!;更佳者為4 〇。 較佳者為S為〇。 當式⑴化合物為氧化物時,較佳者為W為經一至 三個R4基取代之毗啶基。 在所有的敘述中,Me係使用來代表甲基。同樣地Et 代表乙基。 式(Π )化合物
其中RING ’r’R和r3猶如上文中之定義,及a為 NH2,NHCH(O) ’選擇性經取代的((^·4)烷基c(=0)NH,選 擇性經取代的(C〗-4)烷基〇c(=0)NH,鹵素,n02,0S02CF3 13 200526672 或n=c(c6h5)2,其為有用 4用方;製備式⑴化合物的中間體。 其中R3是在盘A支东r? / 一 為郴位的位置與碳原子鍵結的式(m )
化合物具有新藉Η “ JSA 、 車乂仏為做為製備式(I)化合物的中間 因此,本發明的另一個㈣係提供一種式(n)化合物 其中RING,r,R2涞口 r3絲丄 矛R猶如上文中之定義,及A為Nh2 NHCH(O),選擇性經取代的(Ci_4)烧基c卜〇师,選擇性海
取代的(Ck4)烧基〇C( = 〇)NH,Br,j,N〇2,⑽必或 N C(C6H5)2,且R3是在與A為鄰位的位置與碳原子鍵結。 式(I)和(Π )化合物的存在可為不同的幾何或光學異構 物或為不同的互變異構物形式。本發明係包括這些異構物 和互變異構物和它們的所有比例混合物,以及同位素形 例如氘化化合物。 μ ^工 於下歹j表1至2 9中的化合物說明本發明中特別佳的化 合物,其中R5,r6和r7,r4之例子個別獨立地如上所定義。
表Aa係為表ia(當a為i時),表2a(當a為2時),表 3a(當A為3時)及表4a(當A為4時)。 14 .200526672 表Aa
Compound No. τη η Cy Y Rf 5 R6 R7 X A.l H 0 0 Cyl Me3Si H Me cf3 0 A.2 H 0 0 Cyl Me3Si H Me cf2h 0 A.3 H 0 0 Cy2 Me3Si H Me cf3 0 A.4 H 0 0 Cy2 Me3Si H Me cf2h 0 A.5 H 0 0 Cy2 Me3Si H Me cf2ci 0 A.6 H 0 0 Cyl Me3Si H Me cf3 s A.7 炔丙基 0 0 Cy2 Me3Si H Me cf3 0 A. 8 丙二烯基 0 0 Cy2 Me3Si H Me cf3 0 A.9 c〇ch3 0 0 Cy2 Me3Si H Me cf3 0 A.10 Η 0 0 Cy2 Me3Si H CH2OMe cf3 〇 A.ll Η 0 0 Cy2 Me3Si H Me cf2h s A.12 炔丙基 0 0 Cy2 Me3Si H Me cf2h 0 A.13 丙二烯基 0 0 Cy2 Me3Si H Me cf2h 0 A.14 coch3 0 0 Cy2 Me3Si H Me cf2h 〇 A.15 Η 0 0 Cy2 Me3Si H CH2〇Me cf2h 0 A.16 Η 0 0 Cy2 Me3Si F Me Me 〇 A.17 Η 0 0 Cy2 Me3Si F Me cf3 〇 A.18 Η 0 0 Cy2 Me3Si H Me ch2f 〇 A.19 Η 0 0 Cy2 Me3Si Cl Me Me 〇 A.20 Η 0 0 Cyl Me2SiEt H Me cf3 〇 A.21 Η 0 0 Cy2 Me2SiEt H Me cf2h 〇 A.22 Η 0 0 Cy2 Me2SiCHMe2 H Me cf3 〇 A.23 Η 0 0 Cy2 Me2SiCHMe2 H Me cf2h 〇 A.24 Η 1 0 Cy2 Me3Si H Me cf3 〇 A.25 Η 1 0 Cy2 Me3Si H Me cf2h 〇 A.26 Η 0 1 Cy2 Me3Si H Me cf3 〇 A.27 Η 0 1 Cy2 Me3Si H Me cf2h 〇 A.28a Η 0 0 Cy3a Me3Si H Me cf3 〇 A.29a Η 0 0 Cy3a Me3Si H Me cf2h 〇
15 200526672 A.30 H 0 0 Cy4 MesSi H Me cf3 〇 A.31 H 0 0 Cy4 MesSi H Me cf2h 〇 A.32 H 0 0 Cy5 Me3Si H Me cf3 〇 A.33 H 0 0 Cy5 Me3Si H Me cf2h 0 A.34a —H 0 0 Cy6a Me3Si H Me cf3 0 A.35a H 0 0 Cy6a M^Si H Me cf2h 0 A.36 H 0 0 Cy7 Me3Si H Me cf3 〇 A.37 H 0 0 Cy7 Me3Si H Me cf2h 0 A.38 H 0 0 Cy8 Me3Si H Me cf3 0 A.39 H 0 0 Cy8 MesSi H Me cf2h 〇 A.40a H 0 0 Cy9a Me3Si H Me cf3 〇 A.41a H 0 0 Cy9a MesSi H Me cf2h 〇 A.42a H 0 0 CylOa Me3Si H Me cf3 〇 A.43a H 0 0 CylOa Me3Si H Me cf2h 〇 A.44 H 0 1 Cyll H H Me cf3 〇 A.45 H 0 1 Cyll H H Me cf2h 〇 A.46 H 0 1 Cyl2 H H Me cf3 〇 A.47 H 0 1 Cyl2 H H * Me cf2h 〇 A.48 H 0 1 Cyl3 H H Me cf3 〇 A.49 H 0 1 Cyl3 H H Me cf2h 〇 A.50a H 0 1 Cyl4a H H Me cf3 〇 A.51a H 0 1 Cyl4a H H Me cf2h 〇 A.52a 炔丙基 0 1 Cyl4a H H Me cf3 〇 A.53a 丙二烯基 0 1 Cyl4a H H Me cf2h 〇 A.54a 炔丙基 0 1 Cyl4a H H Me cf2h 〇 A.55a 丙二烯基 0 1 Cyl4a H H Me cf3 〇 A.56a Η 0 1 Cyl5a H H Me cf3 〇 A.57a Η 0 1 Cyl5a H H Me cf2h 〇 A.58 Η 0 1 Cyl6 H H Me cf3 〇 A.59 Η 0 1 Cyl6 H H Me cf2h 〇
16 200526672 A.60a H 0 1 Cyl7a H H Me cf3 0 A.61a H 0 1 Cyl7a H H Me CF2H 0 A. 62a 炔丙基 0 1 Cyl7a H H Me cf3〇 A.63a 丙二烯基 0 1 Cyl7a H H Me CF2H 0 A.64a 炔丙基 0 1 Cyl7a H H Me CF2H 0 A.65a 丙二烯基 0 1 Cyl7a H H Me cf3 0 A.66a Η 0 1 Cyl7a H H Me CH2F 0 A.67a Η 0 1 Cyl7a H F Me Me O A.68a Η 0 1 Cyl8a H H Me CF2H 0 A.69a Η 0 1 Cyl8a H H Me cf3 o A.70a Η 0 1 Cyl9a H H Me cf3 0 A.71a Η 0 1 Cyl9a H H Me cf2h o A.72a 炔丙基 0 1 Cyl9a H H Me cf3 o A.73a 丙二烯基 0 1 Cyl9a H H Me cf2h o A.74a 炔丙基 0 1 Cyl9a H H Me cf2h o A.75a 丙二烯基 0 1 Cyl9a H H Me cf3 0 A. 76a Η 0 1 Cyl9a H H Me ch2f o A. 77a Η 0 1 Cyl9a H F Me Me O A.78a Η 0 2 Cyl7a H H Me cf3 o A. 79 Η 0 0 Cy2 Me3Si H cf2h cf3 o A.80 Η 0 0 Cy20 Me2SiCMe3 H Me cf3 o A.81 Η 0 0 Cy20 Me2SiCMe3 H Me cf2h o A.82 Η 0 1 Cy20 Me3Si H Me cf3 o A.83 Η 0 1 Cy20 Me3Si H Me cf2h 0 A.84 Η 0 2 Cy20 Me3Si H Me cf3 0 A.85 Η 0 2 Cy20 Me3Si H Me CF2H 0 A.86 Η 0 0 Cy21 Me3Si H Me cf3 0 A.87 Η 0 0 Cy21 Me3Si H Me CF2H 0 A.88 Η 0 0 Cy22 Me3Si H Me cf3〇 A.89 Η 0 0 Cy22 Me3Si H Me CF2H 〇
17 200526672 A.90 CEO 0 0 Cy22 Me3Si H Me cf3 〇 A.91 CHO 0 0 Cy22 Me3Si H Me cf2h 〇 A.92a H 0 0 Cy23a Me3Si H Me cf3 〇 A.93a H 0 0 Cy23a Me3Si H Me cf2h 〇 A.94a H 0 1 Cy24a H H Me cf3 〇 A.95a H 0 1 Cy24a H H Me cf2h 0 A.96a H 0 2 Cyl7a H H Me cf2h 〇 A.97a H 1 1 Cyl9a H H Me cf3 〇 A.98a H 1 1 Cyl9a H H Me cf2h 0 表Ab係為表lb(當A為1時),表2b(當A為2 時),表3b(當A為3時)及表4b(當A為4時)。 表Ab
Compound No· R1 m η Cy Y R5 R6 R7 X A.28b H 0 0 Cy3b Me3Si H Me cf3 〇 A.29b H 0 0 Cy3b Me3Si H Me cf2h 〇 A.34b H 0 0 Cy6b Me3Si H Me cf3 〇 A.35b H 0 0 Cy6b Me3Si H Me cf2h 〇 A.40b H 0 0 Cy9b Me3Si H Me cf3 〇 A.41b H 0 0 Cy9b Me3Si H Me cf2h 〇 A.42b H 0 0 CylOb Me3Si H Me cf3 〇 A.43b H 0 0 CylOb Me3Si H Me cf2h 〇 A.50b H 0 1 Cyl4b H H Me cf3 〇 A.51b H 0 1 Cyl4b H H Me cf2h 〇 A.52b 炔丙基 0 1 Cyi4b H H Me cf3 〇 A.53b 丙二烯基 0 1 Cyl4b H H Me cf2h 〇 A.54b 炔丙基 0 1 Cyl4b H H Me cf2h 〇 A.55b 丙二烯基 0 1 Cyl4b H H Me cf3 〇 A.56b Η 0 1 Cyl5b H H Me cf3 〇 A.57b Η 0 1 Cyl5b H H Me cf2h 〇 18 200526672 A.60b H 0 1 I Cyl7b H H Me cf3 〇 A.61b H 0 1 Cyl7b H H Me cf2h 〇 A.62b 炔丙基 0 1 Cyl7b H H Me cf3 0 A.63b 丙二烯基 0 1 Cyl7b H H Me cf2h 0 A.64b 炔丙基 0 1 Cyl7b H H Me cf2h 〇 A.65b 丙二烯基 0 1 Cyl7b H H Me cf3 〇 A.66b Η 0 1 Cyl7b H H Me ch2f 〇 A.67b Η 0 1 Cyl7b H F Me Me 〇 A.68b Η 0 1 Cyl8b H H Me cf2h 〇 A.69b Η 0 1 Cyl8b H H Me cf3 〇 A.70b Η 0 1 Cyl9b H H Me cf3 〇 A.71b · Η 0 1 Cyl9b H H Me cf2h 〇 A.72b 炔丙基 0 1 Cyl9b H H Me cf3 〇 A.73b 丙二烯基 0 1 Cyl9b H H Me cf2h 〇 A.74b 炔丙基 0 1 Cyl9b H H Me cf2h 〇 A.75b 丙二烯基 0 1 Cyl9b H H Me cf3 〇 A. 76b Η 0 1 Cyl9b H H Me ch2f 〇 A. 77b Η 0 1 Cyl9b H F .Me Me o A.78b Η 0 2 Cyl7b H H Me cf3 〇 A.92b Η 0 0 Cy23b Me3Si H Me cf3 〇 A.93b Η 0 0 Cy23b Me3Si H Me cf2h 〇 A.94b Η 0 1 Cy24b H H Me cf3 〇 A.95b Η 0 1 Cy24b H H Me cf2h 〇 19 200526672
表la提供98個式(I a)化合物,其中R1,m,η,Cy, R5,R6,R7,Υ和X如表1 a中之定義。 表lb提供39個式(I a)化合物,其中R1,m,η, Cy,R5,R6,R7,Υ和X如表lb中之定義。
(CH2)m-Cy-(CH2)n-Y
表2a提供98個式(I aa)化合物,其中R1,m,η,Cy, R5,R6,R7,Υ和X如表2a中之定義。 表2b提供39個式(I aa)化合物,其中R1,m,η, Cy,R5,R6,R7,Υ和X如表2b中之定義。 20 200526672
表3a提供98個式(I b)化合物,其中R1,m,η,Cy, R5,R6,R7,Υ和X如表3a中之定義。 表3b提供39個式(I b)化合物,其中R1,m,η,
Cy,R5,R6,R7,Υ和X如表3b中之定義。
CH2)m-Cy-(CH2)n-Y
Jo 1 (lb) 表4a提供98個式(I bb)化合物,其中R1,m,n,Cy, R5,R6,R7,Y和X如表4a中之定義。 表4b提供39個式(I bb)化合物,其中R1,m,η, ^
Cy,R5,R6,R7,Υ和X如表4b中之定義。
表Bb係為表5a(當B為5時),表6a(當B為6時),表 7a(當B為7時),表8a(當B為8時),表9a(當B為9時) 21 200526672 時)及表l〇a(當B為10時)。 表Ba
Compound No. R1 m η Cy Y R5 R6 X B.l Η 0 0 Cyl Me3Si Me cf3 o B.2 Η 0 0 Cyl Me3Si Me cf2h 0 Β·3 Η 0 0 Cy2 Me3Si Me cf3 〇 Β·4 Η 0 0 Cy2 Me3Si Me cf2h 0 Β·5 Η 0 0 Cy2 Me3Si Me cf2ci o Β·6 Η 0 0 Cy2 MesSi Me cf3 s Β.7 炔丙基 0 0 Cyl Me3Si Me cf3 〇 Β.8 丙二烯基 0 0 Cy2 Me3Si Me cf3 o Β·9 c〇ch3 0 0 Cyl Me3Si Me cf3 〇 Β.10 Η 0 0 Cy2 Me3Si CH2OMe cf3 o Β.11 Η 0 0 Cy2 Me3Si Me cf2h s Β.12 炔丙基 0 0 Cy2 Me3Si Me cf2h 〇 Β.13 丙二烯基 0 0 Cy2 Me3Si Me cf2h 〇 Β.14 c〇ch3 0 0 Cy2 MesSi Me cf2h 〇 Β.15 Η 0 0 Cy2 Me3Si CH2〇Me cf2h 〇 Β.16 Η 0 0 C.y2 Me3Si Me Me 〇 Β.17 Η 0 0 Cy2 MesSi cf3 Me 〇 Β.18 Η 0 0 Cy2 Me3Si Me ch2f 〇 Β.19 Η 0 0 Cy2 Me3Si Me ch2f 〇 Β.20 Η 0 0 Cy2 Me2SiEt Me cf3 〇 Β.21 Η 0 0 Cy2 Me2SiEt Me cf2h 〇 Β.22 Η 0 0 Cy2 Me2SiCHMe2 Me cf3 〇 Β.23 Η 0 0 Cyl Me2SiCHMe2 Me cf2h 〇 Β.24 Η 1 0 Cy2 Me3Si Me cf3 〇 Β.25 Η 1 0 Cyl Me3Si Me cf2h 〇
22 200526672 B.26 H 0 1 Cy2 Me3Si Me cf3 〇 B.27 H 0 1 Cy2 Me3Si Me cf2h 〇 B.28a H 0 0 Cy3a Me3Si Me cf3 〇 B.29a H 0 0 Cy3a MC3S1 Me cf2h 〇 B.30 H 0 0 Cy4 M^Si Me cf3 〇 B.31 H 0 0 Cy4 MesSi Me cf2h 〇 B.32 H 0 0 Cy5 MesSi Me cf3 〇 B.33 H 0 0 Cy5 MesSi .Me cf2h 〇 B.34a H 0 0 Cy6a MesSi Me cf3 〇 B.35a H 0 0 Cy6a MesSi Me cf2h 〇 B.36 H 0 0 Cy7 MesSi Me cf3 〇 B.37 H 0 0 Cy7 Me3Si Me cf2h 〇 B.38 H 0 0 Cy8 Me3Si Me cf3 〇 B.39 H 0 0 Cy8 , Me3Si Me cf2h 〇 B.40a H 0 0 Cy9a MesSi Me cf3 0 B.41a H 0 0 Cy9a MeaSi Me cf2h 〇 B.42a H 0 0 CylOa Me3Si Me cf3 〇 B.43a H 0 0 CylOa Me3Si Me cf2h 〇 B.44 H 0 1 Cyll H Me cf3 〇 B.45 H 0 1 Cyll H Me cf2h 〇 B.46 H 0 1 Cyl2 H Me cf3 〇 B.47 H 0 1 Cyl2 H Me cf2h 〇 B.48 H 0 1 Cyl3 H Me cf3 〇 B.49 H 0 1 Cyl3 H Me cf2h 〇 B.50a H 0 1 Cyl4a H Me cf3 〇 B.51a H 0 1 Cyl4a H Me cf2h 〇 B.52a 炔丙基 0 ] Cyl4a H Me cf3 〇 B.53a 丙二烯基 0 Cyl4a H Me cf2h 〇 B.54a 炔丙基 0 Cyl4a H Me cf2h 〇 B.55a 丙二烯基 0 1 Cyl4a H Me cf3 〇 23 200526672 B.56a H 0 1 Cyl5a H Me cf3 〇 B.57a H 0 1 Cyl5a H Me cf2h 0 B.58 H 0 1 Cyl6 H Me cf3 〇 B.59 H 0 1 Cyl6 H Me cf2h 〇 B.60a H 0 1 Cyl7a H Me cf3 〇 B.61a H 0 1 Cyl7a H Me cf2h 〇 B.62a 炔丙基 0 1 Cyl7a H Me cf3 〇 B.63a 丙二烯基 0 1 Cyl7a H Me cf2h 〇 B.64a 炔丙基 0 1 Cyl7a H Me cf2h 〇 B.65a 丙二烯基 0 1 Cyl7a H Me cf3 〇 B.66a Η 0 1 Cyl7a H Me ch2f 〇 B.67a Η 0 1 Cyl7a H Me Me 〇 B.68a Η 0 1 Cyl8a H Me cf2h 〇 B.69a Η 0 1 CylSa H Me cf3 〇 B.70a Η 0 1 Cyl9a H Me cf3 〇 B.71a Η 0 1 Cyl9a H Me cf2h 〇 B.72a 炔丙基 0 1 Cyl9a H Me cf3 〇 B.73a 丙二烯基 0 1 Cyl9a H Me cf2h 〇 B.74a 炔丙基, 0 1 Cyl9a H Me cf2h 〇 B.75a 丙二烯基: 0 1 Cyl9a H Me cf3 〇 B.76a Η 0 1 Cyl9a H Me ch2f 〇 B.77a Η 0 1 Cyl9a H Me Me 〇 B.78a Η 0 2 Cyl7a H Me cf3 〇 B.79a Η 0 2 Cyl7a H Me cf2h 〇 B.80 Η 0 0 Cy20 Me2SiCMe3 Me cf3 〇 B.81 Η 0 0 Cy20 Me2SiCMe3 Me cf2h 〇 B.82 Η 0 1 Cy20 Me3Si Me cf3 〇 B.83 Η 0 1 Cy20 Me3Si Me cf2h 〇 B.84 Η 0 2 Cy20 Me3Si Me cf3 〇 B.85 Η 0 2 Cy20 Me3Si Me cf2h 〇
24 200526672 B.86 H 0 0 Cy21 Me3Si Me cf3 〇 B.87 H 0 0 Cy21 Me3Si Me cf2h 〇 B.88 H 0 0 Cy22 Me3Si Me cf3 〇 B.89 H 0 0 Cy22 Me3Si Me cf2h 〇 B.90 CH〇 0 0 Cy22 Me3Si Me cf3 〇 B.91 CHO 0 0 Cy22 Me3Si Me cf2h 〇 B.92a H 0 0 Cy23a Me3Si Me . cf3 〇 B.93a H 0 0 Cy23a Me3Si Me cf2h 〇 B.94a H 0 1 Cy24a H Me cf3 〇 B.95a H 0 1 Cy24a H Me cf2h 〇 B.96a H 0 2 Cyl7a H Me cf2h 〇 B.97a H 1 1 Cyl9a H Me cf3 〇 B.98a H 1 1 Cyl9a H Me cf2h 〇
表Bb係為表5b(當B為5時),表6b(當B為6時), 表7b(當B為7時),表8b(當B為8時),表9b(當B為9 時)及表10b(當B為10時)。 表Bb
Compound No. R1 IB u Cy Y R5 R6 X B.28b H 0 0 Cy3b Me3Si Me cf3 〇 B.29b H 0 0 Cy3b Me3Si Me cf2h 〇 B.34b H 0 0 Cy6b Me3Si Me cf3 〇 B.35b H 0 0 Cy6b Me3Si Me cf2h 〇 B.40b H 0 0 Cy9b Me3Si Me cf3 〇 B.41b H 0 0 Cy9b Me3Si Me cf2h 〇 B.42b H 0 0 CylOb Me3Si Me cf3 〇 B.43b H 0 0 CylOb Me3Si Me cf2h 〇 B.50b H 0 1 Cyl4b H Me cf3 〇 B.51b H 0 1 Cyl4b H Me cf2h 〇 B.52b 炔丙基 0 1 Cyl4b H Me cf3 〇 B.53b 丙二烯基 0 1 Cyl4b H Me cf2h 〇 : 25 200526672 B.54b 炔丙基 0 1 Cyl4b H Me CF2H 0 B.55b 丙二烯基 0 1 Cyl4b H Me cf3 〇 B.56b Η 0 1 Cyl5b H Me cf3 〇 B.57b Η 0 1 Cyl5b H Me cf2h 〇 B.60b Η 0 1 Cyl7b H Me cf3 0 B.61b Η 0 1 Cyl7b H Me cf2h 〇 B.62b 炔丙基 0 1 Cyl7b H Me cf3 〇 B.63b 丙二烯基 0 1 Cyl7b H Me cf2h 〇 B.64b 炔丙基 0 1 Cyl7b H Me cf2h 0 B.65b 丙二烯基 0 1 Cyl7b H Me cf3 〇 B.66b Η 0 1 Cyl7b H Me ch2f 〇 B.67b Η 0 1 Cyl7b H Me Me 〇 B.68b Η 0 1 Cyl8b H Me cf2h 〇 B.69b Η 0 1 Cyl8b H Me cf3 〇 B.70b Η 0 1 Cyl9b H Me cf3 o B.71b Η 0 1 Cyl9b H Me cf2h 〇 B.72b 炔丙基 0 1 Cyl9b H Me cf3 〇 B.73b 丙二烯基 0 1 Cyl9b H Me . cf2h 〇 B.74b 炔丙基 0 1 Cyl9b H Me cf2h 〇 B.75b 丙二烯基, 0 1 Cyl9b H Me cf3 〇 B.76b Η 0 1 Cyl9b H Me ch2f 〇 B.77b Η 0 1 Cyl9b H Me Me 〇 B.78b Η 0 2 Cyl7b H Me cf3 〇 B.79b Η 0 2 Cyl7b H Me cf2h 〇 B.92b Η 0 0 Cy23b Me3Si Me cf3 〇 B.93b Η 0 0 Cy23b Me3Si Me cf2h 〇 B.94b Η 0 1 Cy24b H Me cf3 〇 B.95b Η 0 1 Cy24b H Me cf2h 〇
26 200526672 表5a提供98個式(I c)化合物,其中R1,m,η,Cy, R5,R6,Υ和X如表5a中之定義。 表5b提供40個式(I c)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表5b中之定義。
(CH2)m-Cy-(CH2)n-Y
表6a提供98個式(I cc)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表6a中之定義。 表6b提供40個式(I cc)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表6b中之定義。
(CH2)m-Cy>(CH2)n-Y
表7a提供98個式(I d)化合物,其中R1,m,η,Cy, R5,R6,Υ和X如表7a中之定義。 表7b提供40個式(I d)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表7b中之定義。 27 200526672
(CH2)m-Cy-(CH2)n-Y
表8a提供98個式(I dd)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表8a中之定義。 表8b提供40個式(I dd)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表8b中之定義。
(CH2)m-Cy-(CH2)n-Y
表9a提供98個式(I e)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表9a中之定義。 表9b提供40個式(I e)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表9b中之定義。 (CH2)m-Cy-(CH2)n•丫
表1 Oa提供98個式(I ee)化合物,其中R1,m,η,Cy, R5,R6,Y和X如表1 Oa中之定義。 28 200526672 表l〇b提供40個式(I ee)化合物,其中R1,m,n,Cy, R5,R6,Υ和X如表1 Ob中之定義。
(CH2)m-Cy-(CH2)n-Y
4 (lee) 表Ca係為表11a(當C為11時),表12a(當C為12時), 表13a(當C為13時),及表14a(當C為14時)。 籲 表Ca
Compound No. R】 m n Cy Y R5 R6 R7 X C.l H 0 0 Cyl Me3Si H Me cf3 〇 C.2 H 0 0 Cyl Me3Si H Me cf2h 〇 C.3 H 0 0 Cyl Me3Si H Me cf3 〇 C.4 H 0 0 Cy2 Me3Si H Me cf2h 〇 C.5 H 0 0 Cy2 Me3Si H Me cf2ci 0
29 200526672 C.6 H 0 0 Cy2 Me3Si H Me cf3 s C.7 H 0 0 Cy2 Me3Si Me Me cf3 〇 C.8 H 0 0 Cy2 Me3Si H H cf3 〇 C.9 H 0 0 Cy2 Me3Si Me H cf3 〇 C.10 H 0 0 Cy2 Me3Si Me Me Me 〇 C.ll H 0 0 Cy2 Me3Si Me Me H 0 C.12 炔丙基! 0 0 Cy2 Me3Si H Me cf3 〇 C.13 丙土烯塞 0 0 Cy2 Me3Si H Me cf3 〇 C.14 c〇ch3 0 0 Cy2 Me3Si H Me cf3 〇 C.15 Η 0 0 Cy2 Me3Si H Me ch2f 〇 C.16 Η 1 0 Cy2 Me3Si H Me cf3 〇 C.17 Η 1 0 Cy2 Me3Si H Me cf2h 〇 C.18 Η 0 1 Cy2 Me3Si H Me cf3 〇 C.19 Η 0 1 Cy2 Me3Si H Me cf2h 〇 C.20a Η 0 0 Cy3a Me3Si H Me cf3 0 C.21a Η 0 0 Cy3a Me3Si H Me cf2h 〇 C.22 Η 0 0 Cy4 Me3Si H Me cf3 0 C.23 Η 0 0 Cy4 Me3Si H Me cf2h 0 C.24 Η 0 0 Cy5 Me3Si H Me cf3 〇 C.25 Η 0 0 Cy5 Me3Si H Me cf2h 〇 C.26a Η 0 0 Cy6a Me3Si H Me cf3 〇 C.27a Η 0 0 Cy6a Me3Si H Me cf2h o C.28 Η 0 0 Cy7 Me3Si H Me cf3 〇 C.29 Η 0 0 Cy7 Me3Si H Me cf2h 〇 C.30 Η 0 0 Cy8 Me3Si H Me cf3 〇 C.31 Η 0 0 Cy8 Me3Si H Me cf2h 0 C.32a Η 0 0 Cy9a Me3Si H Me cf3 〇 C.33a Η 0 0 Cy9a Me3Si H Me cf2h 〇 C.34a Η 0 0 CylOa Me3Si H Me cf3 〇 C.35a Η 0 0 CylOa Me3Si H Me cf2h 〇
30 200526672 C.36 H 0 !1 Cyll H H Me cf3 0 C‘37 H 0 1 Cyll H H Me cf2h 〇 C.38 H 0 1 Cyl2 H H Me cf3 0 C.39 H 0 1 Cyl2 H H Me cf2h 0 C.40 H 0 1 Cyl3 H H Me cf3 0 C.41 H 0 1 Cyl3 H H Me cf2h 〇 C.42a H 0 1 Cyl4a H H Me cf3 〇 C.43a H 0 1 Cyl4a H H Me cf2h 〇 C.44a H 0 1 Cyl4a H Me Me cf3 〇 C.45a H 0 1 Cyl4a H H H cf3 〇 C.46a H 0 1 Cyl4a H Me H cf3 〇 C.47a H 0 1 Cyl4a H Me Me Me 〇 C.48a H 0 1 Cyl4a H Me Me H 〇 C.49a H 0 1 Cyl5a H Me Me cf3 〇 C.50a H 0 1 Cyl5a H H Me cf2h 〇 C.51 H 0 1 Cyl6 H H Me cf3 〇 C.52 H 0 1 Cyl6 H H Me cf2h 〇 C.53a H 0 1 Cyl7a H H Me cf3 〇 C.54a H 0 1 Cyl7a H H Me cf2h 〇 C.55a H 0 1 Cyl7a H Me Me cf3 〇 C.56a H 0 1 Cyl7a H H H cf3 〇 C.57a H 0 1 Cyl7a H Me H cf3 〇 C.58a H 0 1 Cyl7a H Me Me Me 〇 C.59a H 0 1 Cyl7a H Me Me H 〇 C.60a H 0 1 Cyl8a H H Me CF2H 〇 C.61a H 0 1 Cyl8a H H Me cf3 〇 C.62a H 0 1 Cyl9a H H Me cf3 〇 C.63a H 0 1 Cyl9a H H Me cf2h 〇 C.64a H 0 1 Cyl9a H Me Me cf3 〇 C.65a H 0 1 Cyl9a H H H cf3 〇 31 200526672 C.66a H 0 1 Cyl9a H Me H cf3 〇 C.67a H 0 1 Cyl9a H Me Me Me 0— —C.68a H 0 1 Cyl9a H Me Me H 〇一 C.69a H 0 2 Cyl7a H H Me cf3 0— C.70a H 0 2 Cyl7a H H Me cf2h 〇 C.71 H 0 0 Cy20 Me2SiCMe3 H Me cf3 〇 C.72 H 0 0 Cy20 Me2SiCMe3 H Me cf2h 〇 C.73 H 0 1 Cy20 Me3Si H Me cf3 〇 C.74 H 0 2 Cy20 Me3Si H Me cf3 0 C.75 H 0 0 Cy21 Me3Si H Me cf3 〇 C.76 H 0 0 Cy22 Me3Si H Me cf3 〇 C.77 CHO 0 0 Cy22 ’丨 Me3Si H Me cf3 〇 C.78a H 0 0 Cy23a Me3Si H Me cf3 〇 C.79a H 0 1 Cy24a H H Me cf2h 〇 C.80a H 0 1 Cy24a H Me Me cf3 〇 表Cb係為表lib(當C為11時),表12b(當C為12 時),表13b(當C為13時),及表14b(當C為14時)。 表Cb
Compound No. R] m n Cy Y R5 R6 R7 X C.20b H 0 0 Cy3b Me3Si H Me cf3 〇 C.21b H 0 0 Cy3b Me3Si H Me cf2h 〇 C.26b H 0 0 Cy6b Me3Si H Me cf3 〇 C.27b H 0 0 Cy6b Me3Si H Me cf2h 〇 C.32b H 0 0 Cy9b MesSi H Me cf3 〇 C.33b H 0 0 Cy9b Me3Si H Me cf2h 〇 C.34b H 0 0 CylOb Me3Si H Me cf3 〇 C.35b H 0 0 CylOb MaSi H Me cf2h 〇 C.42b H 0 1 Cyl4b H H Me cf3 〇 C.43b H 0 1 Cyl4b H H Me cf2h 〇 C.44b H 0 1 Cyl4b H Me Me cf3 0 32 200526672 C.45b H 0 1 Cyl4b H H H cf3 〇 C.46b H 0 1 Cyl4b H Me H cf3 〇 C.47b H 0 1 Cyl4b H Me Me Me 〇 C.48b H 0 1 Cyl4b H Me Me H 〇 C.49b H 0 1 Cyl5b H Me Me cf3 〇 C.50b H 0 1 Cyl5b H H Me cf2h 〇 C.53b H 0 1 Cyl7b H H Me cf3 〇 C.54b H 0 1 Cyl7b H H Me cf2h 〇 C.55b H 0 1 Cyl7b H Me Me cf3 o C.56b H 0 1 Cyl7b H H H cf3 〇 C.57b H 0 1 Cyl7b H Me H cf3 〇 C.58b H 0 1 Cyl7b H Me Me Me 〇 C.59b H _ 0 1 Cyl7b H Me Me H 〇 C.60b H 0 1 Cyl8b H H Me CF2H 〇 C.61b H 0 1 Cyl8b H H Me cf3 〇 C.62b H 0 1 Cyl9b H H Me cf3 〇 C.63b H 0 1 Cyl9b H H Me cf2h 〇 C.64b H 0 1 Cyl9b H Me Me cf3 〇 C.65b H 0 1 Cyl9b H H H cf3 〇 C.66b H 0 1 Cyl9b H Me H cf3 〇 C.67b H 0 1 Cyl9b H Me Me Me 〇 C.68b H 0 1 Cyl9b H Me Me H 〇 C.69b H 0 2 Cyl7b H H Me cf3 〇 C.70b H 0 2 Cyl7b H H Me cf2h 〇 C.78b H 0 0 Cy23b Me3Si H Me cf3 〇 C.79b H 0 1 Cy24b H H Me cf2h 〇 C.80b H 0 1 Cy24b H Me Me cf3 〇 33 200526672 表lla提供80個式(I f)化合物,其中R],m,η,Cy, R5,R6,R7,Υ和X如表1 1 a中之定義。 表lib提供38個式(I f)化合物,其中R1,m,η,Cy, R5,R6,R7,Y和X如表1 1 b中之定義。
(CH2)m-Cy-(CH2)n-Y
• 表12a提供80個式(I ff)化合物,其中R1,m,η,Cy, R5,R6,R7,Υ和X如表12a中之定義。 表12b提供38個式(I f)化合物,其中R1,m,η,Cy, R5,R6,R7,Y和X如表12b中之定義。
(CH2)m-Cy-(CH2)n-Y
表13a提供80個式(I g)化合物,其中R1,!)!,n,Cy, R5,R6,R7,Y和X如表13a中之定義。 表13b提供38個式(I g)化合物,其中R1,!!!,n,Cy, R5,R6,R7,Y和X如表13b中之定義。 34 200526672
(CH2)m-C-(CH2)n-Y
表14a提供80個式(I gg)化合物,其中R1,m,n,Cy, R5,R6,R7,Y和X如表14a中之定義。 表14b提供38個式(I gg)化合物,其中R1,!!!,n,Cy, R5,R6,R7,Y和X如表14b中之定義。
(CH2)m-Cy-(CH2)n-Y
R7 X
表Da係為表15a(當D為15時),表16a(當D為16 時),表17a(當D為17時),表18a(當D為18時),表19a(當 D為19時)及表20a(當D為20時)。 35 200526672 表Da
Compound No. R1 m η Cy Y R5 X D.l H 0 0 Cyl Me3Si cf3 〇 D.2 H 0 0 Cyl Me3Si Me 〇 D.2 H 0 0 Cy2 Me3Si cf3 〇 D.3 H 0 0 Cy2 Me3Si Me 〇 D.4 H 0 0 Cyl Me3Si CF2C1 〇 D.5 H 0 0 Cy2 Me3Si cf3 s D.7 炔丙基 0 0 Cy2 Me3Si cf3 0 D.8 丙二烯基 0 0 Cy2 Me3Si cf3 〇 D.9 coch3 0 0 Cy2 Me3Si cf3 〇 D.10 Η 0 0 Cy2 Me3Si Me s D.ll 炔丙基 0 0 Cy2 Me3Si Me 0 D.12 丙二烯基 0 0 Cy2 Me3Si Me 〇 D.13 coch3 0 0 Cy2 Me3Si Me 〇 D.14 Η 1 0 Cy2 Me3Si cf3 0 D.15 Η 1 0 Cy2 Me3Si Me 〇 D.16 Η 0 1 Cy2 Me3Si cf3 〇 D.17 Η 0 1 Cy2 Me3Si Me 〇 D.18a Η 0 0 Cy3a Me3Si cf3 〇 D.19a Η 0 0 Cy3a M&Si Me 〇 D.20 Η 0 0 Cy4 Me3Si cf3 〇 D.21 Η 0 0 Cy4 Me3Si cf2h 〇 D.22 Η 0 0 Cy5 Me3Si cf3 〇 36 200526672 D.23 H 0 0 Cy5 Me3Si Me 〇 D.24a H 0 0 Cy6a Me3Si cf3 〇 D.25a H 0 0 Cy6a Me3Si Me 〇 D.26 H 0 0 Cy7 Me3Si cf3 〇 D.27 H 0 0 Cy7 Me3Si Me 〇 D.28 H 0 0 Cy8 Me3Si CF? 〇 D.29 H 0 0 Cy8 Me3Si Me 〇 D.30a H 0 0 Cy9a Me3Si cf3 〇 D.31a H 0 0 Cy9a Me3Si Me 〇 D.32a H 0 0 CylOa Me3Si cf3 〇 D.33a H 0 0 CylOa Me3Si Me 〇 D.34 H 0 1 Cyll H cf3 0 D.35 H 0 1 Cyll H Me 0 D.36 H 0 1 Cyl2 H cf3 〇 D.37 H 0 1 Cyl2 H Me o D.38 H 0 1 Cyl3 H cf3 〇 D.39 H 0 1 Cyl3 H Me 〇 D.40a H 0 1 Cyl4a H cf3 〇 D.41a H 0 1 Cyl4a H Me 〇 D.42a 炔丙基 0 1 Cyl4a H cf3 〇 D.43a 丙二烯基 0 1 Cyl4a H Me 〇 D.44a 炔丙基 0 1 Cyl4a H Me 〇 D.45a 丙二烯基 1 0 1 Cyl4a H cf3 〇 D.46a Η 0 1 Cyl5a H cf3 〇 D.47a Η 0 1 Cyl5a H Me 〇 D.48 Η 0 1 Cyl6 H cf3 〇 D.49 Η 0 1 Cyl6 H Me 〇 D.50a Η 0 1 Cyl7a H cf3 〇 D.51a Η 0 1 Cyl7a H Me 〇 D.52a 炔丙基 0 1 Cyl7a H cf3 〇 37 200526672 D.53a 丙二烯基 0 1 Cyl7a H Me 〇 D.54a 炔丙基 0 1 Cyl7a H Me 〇 D.55a 丙二烯基 0 1 Cyl7a H cf3 〇 D.56a Η 0 1 Cyl8a H Me 〇 D.57a Η 0 1 Cyl8a H cf3 〇 D.58a Η 0 1 Cyl9a H cf3 〇 D.59a Η 0 1 Cyl9a H Me 〇 D.60a 炔丙基 0 1 Cyl9a H cf3 〇 D.61a 丙二烯基 0 1 Cyl9a H Me 〇 D.62a 炔丙基‘ 0 1 Cyl9a H Me 〇 D.63a 丙二烯基 0 1 Cyl9a H cf3 〇 D.64a Η 0 2 Cyl7a H cf3 〇 D.65a Η 0 2 CyI7a H Me 〇 D.66 Η 0 0 Cy20 Me2SiCMe3 cf3 0 D.67 Η 0 0 Cy20 Me2SiCMe3 Me 〇 D.68 Η 0 1 Cy20 Me3Si cf3 〇 D.69 Η 0 1 Cy20 Me3Si Me 〇 D.70 Η 0 2 Cy20 Me3Si cf3 〇 D.71 Η 0 2 Cy20 Me3Si Me 〇 D.72 Η 0 0 Cy21 Me3Si cf3 〇 D.73 Η 0 0 Cy21 Me3Si Me 〇 D.74 Η 0 0 Cy22 Me3Si cf3 〇 D.75 Η 0 0 Cy22. Me3Si Me 〇 D.76 CHO 0 0 Cy22 Me3Si cf3 〇 D.77 CHO 0 0 Cy22 Me3Si Me 〇 D.78a Η 0 0 Cy23a Me3Si cf3 〇 D.79a Η 0 0 Cy23a Me3Si Me 〇 D.80a Η 0 1 Cy24a H cf3 〇 D.81a Η 0 1 Cy24a H Me 〇
38 200526672 表Db係為表15b(當D為15時),表16b(當D為16 時),表17b(當D為17時),表18b(當D為18時),表19b(當 D為19時)及表20b(當D為20時)。 表Db
Compound No. R1 m η Cy Y R5 X D.18b H 0 0 Cy3b Me3Si cf3 〇 D.19b H 0 0 Cy3b Me3Si Me 〇 D.24b H 0 0 Cy6b Me3Si cf3 〇 D.25b H 0 0 Cy6b Me3Si Me 〇 D.30b H 0 0 Cy9b Me3Si cf3 〇 D.31b H 0 0 Cy9b Me3Si Me 〇 D.32b H 0 0 CylOb Me3Si cf3 〇 D.33b H 0 0 CylOb Me3Si Me 〇 D.40b H 0 1 Cyl4b H cf3 〇 D.41b H 0 1 Cyl4b H Me 〇 D.42b 炔丙基1 0 1 Cyl4b H cf3 〇 D.43b 丙二烯基 0 1 Cyl4b H Me 〇 D.44b 炔丙基 0 1 Cyl4b H Me 〇 D.45b 丙二烯基 0 1 Cyl4b H cf3 〇 D.46b Η 0 1 Cyl5b H cf3 〇 D.47b Η 0 1 Cyl5b H Me 〇 D.50b Η 0 1 Cyl7b H cf3 〇 D.51b Η 0 1 Cyl7b H Me 〇 D.52b 炔丙基1: 0 1 Cyl7b H cf3 〇 D.53b 丙二烯基 0 1 Cyl7b H Me 〇 D.54b 炔丙基 0 1 Cyl7b H Me 〇 D.55b 丙二烯基 0 1 Cyl7b H cf3 〇 D.56b Η 0 1 Cyl8b H Me 〇 D.57b Η 0 1 Cyl8b H cf3 〇 D.58b Η 0 1 Cyl9b H cf3 〇 D.59b Η 0 1 Cyl9b H Me 〇 39 200526672 D.60b 炔丙基 0 1 Cyl9b H cf3 〇 D.61b 丙二烯基 0 1 Cyl9b H Me 0 D.62b :炔丙基 0 1 Cyl9b H Me 〇 D.63b 丙二烯基 0 1 Cyl9b H cf3 0 D.64b Η 0 2 Cyl7b H cf3 〇 D.65b Η 0 2 Cyl7b H Me 〇 D.78b Η 0 0 Cy23b Me3Si cf3 〇 D.79b Η 0 0 Cy23b Me3Si Me 〇 D.80b Η 0 1 Cy24b H cf3 〇 D.81b Η 0 1 Cy24b H Me 〇
表15a提供81個式(I h)化合物,其中R1,m,η,Cy, R5,Υ和X如表15a中之定義。 表15b提供36個式(I h)化合物,其中R1,m,η,Cy, R5,Y和X如表1 5b中之定義。
表16a提供81個式(I hh)化合物,其中 R5,Y和X如表1 6a中之定義。 表16b提供36個式(Ihh)化合物,其中Rhun^Cy, R5,Y和X如表1 6b中之定義。 40 200526672
(CH2)m-C-(CH2)n-Y
R* R· 表17a提供81個式(I j)化合物,其中R1,m,n,Cy Y和X如表17a中之定義。 表17b提供36個式(I j)化合物,其中R1,m,η,Cy Υ和X如表17b中之定義。 (CH2)m-C,(CH2),丫
R- R- 表18a提供81個式(I jj)化合物,其中R1,m,η,Cy Y和X如表18a中之定義。 表18b提供36個式(I jj)化合物,其中R1,m,η,Cy Y和X如表18b中之定義。
(CH2)m-C-(CH2)n-Y
(IJJ) 表19a提供81個式(I k)化合物,其中R1,m,η,Cy 41 -200526672 R5,Y和X如表1 9a中之定義。 表19b提供36個式(I k)化合物,其中R1,m,η,Cy, R5,Y和X如表1 9b中之定義。
(CH2)m-Cy-(CH2)n-Y
表20a提供81個式(I kk)化合物,其中R1,m,n,Cy, R5,Y和X如表20a中之定義。 表20b提供36個式(I kk)化合物,其中R1,m,n,Cy, R5,Y和X如表20b中之定義。
(CH2)m-Cy-(CH2)n-Y
表Ea係為表21a(當E為21時),表22a(當E為22時), 表23a(當E為23時),表24a(當E為24時),表25a(當E 為25時)及表26a(當E為26時)。 42 •200526672 表Ea
Compound No. R1 m η cy Y R5 X E.l H 0 0 Cyl Me^Si cf3 〇 E.2 H 0 0 Cyl Me3Si Cl 〇 E.3 H 0 0 Cy2 Me3Si Cl 〇 E.4 H 0 0 Cy2 Me3Si CF2C1 〇 E.5 H 0 0 Cy2 Me3Si cf3 〇 E.7 炔丙基 0 0 Cy2 Me3Si cf3 〇 E.8 丙二烯基 0 0 Cy2 Me3Si cf3 〇 E.9 c〇ch3 0 0 Cy2 Me3Si cf3 〇 E.10 Η 0 0 Cy2 Me3Si Cl s E.ll :炔丙基 0 0 Cy2 Me3Si Cl 〇 E.12 丙二烯基 0 0 Cy2 Me3Si Cl 〇 E.13 c〇ch3 0 0 Cy2 Me3Si Cl 〇 E.14 Η 1 0 Cy2 Me3Si cf3 〇 E.15 Η 1 0 Cy2 Me3Si Cl 〇 E.16 Η 0 1 Cy2 Me3Si cf3 〇 E.17 Η 0 1 Cy2 Me3Si Cl 〇 E.18a Η 0 〇 Cy3a Me3Si cf3 〇 E.19a Η 0 0 Cy3a Me3Si Cl 〇 E.20 Η 0 0 Cy4 Me3Si cf3 〇 E.21 Η 0 0 Cy4 Me3Si Cl 〇 E.22 Η 0 0 Cy5 Me3Si cf3 〇 E.23 Η 0 0 Cy5 Me3Si c] 〇 43 200526672 E.24a H 0 0 Cy6a Me3Si cf3 〇 E.25a H 0 0 Cy6a Me3Si Cl 0 E.26 H 0 0 Cy7 Me3Si cf3 〇 E.27 H 0 0 Cy7 Me3Si Cl 0 E.28 H 0 0 Cy8 Me3Si cf3 〇 E.29 H 0 0 Cy8 Me3Si Cl 〇 E.30a H 0 0 Cy9a Me3Si cf3 〇 E.31a H 0 0 Cy9a Me3Si Cl 〇 E.32a H 0 0 CylOa Me3Si cf3 · 〇 E.33a H 0 0 CylOa Me3Si Cl 〇 E.34 H 0 1 Cyll H cf3 〇 E.35 H 0 1 Cyll H Cl 〇 E.36 H 0 1 Cyl2 H CFs 〇 E.37 H 0 1 Cyl2 H Cl 〇 E.38 H 0 1 Cyl3 H cf3 〇 E.39 H 0 1 Cyl3 H Cl 〇 E.40a H 0 1 Cyl4a H cf3 〇 E.41a H 0 1 Cyl4a H Cl 〇 E.42a :炔丙基 0 1 Cyl4a H cf3 〇 E.43a 丙二烯基 0 1 Cyl4a H Cl 〇 E.44a ;炔丙S 0 1 Cyl4a H Cl 〇 E.45a 丙二讎 0 1 Cyl4a H cf3 〇 E.46a Η 0 1 Cyl5a H cf3 〇 E‘47a Η 0 j Cyl5a H Cl 〇 E.48 Η 0 1 Cyl6 H cf3 〇 E.49 Η 0 1 Cyl6 H Cl 〇 E.50a Η 0 1 Cyl7a H cf3 〇 E.51a Η 0 1 Cyl7a H Cl 〇 E.52a ;炔丙基 0 1 Cyl7a H cf3 〇 E.53a 丙二烯基 0 1 Cyl7a H Cl 〇
44 200526672 E.54a :炔丙基 0 1 Cyl7a H Cl 〇 E.55a 丙二烯基 :0 1 Cyl7a TT CF3 Q E.56a Η 0 1 Cyl8a H Cl 〇 E.57a Η 0 1 Cyl8a H cf3 〇 E.58a Η 0 1 Cyl9a H cf3 〇 E.59a Η 0 1 Cyl9a H Cl 〇 E.60a :炔丙基 0 1 .Cyl9a H cf3 〇 E.61a 丙二烯基 0 1 Cyl9a H Cl 〇 E.62a :炔丙基 0 1 Cyl9a H Cl 〇 E.63a 丙二烯基 0 1 Cyl9a H CFs 〇 E.64a Η 0 2 Cyl7a H cf3 〇 E.65a Η 0 2 Cyl7a H Cl 〇 E.66 Η 0 0 Cy20 Me2SiCMe3 cf3 〇 E.67 Η 0 0 Cy20 Me2SiCMe3 Cl 〇 E.68 Η 0 1 Cy20 Me3Si cf3 〇 E.69 Η 0 1 Cy20 Me3Si Cl 〇 E.70 Η 0 2 Cy20 Me3Si cf3 〇 E.71 Η 0 2 Cy20 Me3Si Cl 〇 E.72 Η 0 0 Cy21 Me3Si cf3 〇 E.73 Η 0 0 Cy21 Me3Si Cl 〇 E.74 Η 0 0 Cy22 Me3Si cf3 〇 E.75 Η 0 0 Cy22 Me3Si Cl 〇 E.76 CHO 0 0 Cy22 Me3Si cf3 〇 E.77 CHO 0 0 Cy22 Me3Si Cl 〇 E.78a Η 0 0 Cy23a Me3Si cf3 〇 E.79a Η 0 0 Cy23a Me3Si Cl 〇 E.80a Η 0 1 Cy24a H cf3 0 E.81a Η 0 1 Cy24a H Cl 〇 E.82a Η 0 2 Cyl7a H Cl 〇 E.83a Η 1 1 Cyl9a H Cl 〇
45 200526672 表Eb係為表21b(當E為21時),表22b(當E為22時), 表23b(當E為23時),表24b(當E為24時),表25b(當E 為25時)及表26b(當E為26時)。 表Eb
Compound No. R1 m η Cy Y R5 X E.18b H 0 0 Cy3b Me3Si cf3 〇 E.19b H 0 0 Cy3b Me3Si Cl 〇 E.24b H 0 0 Cy6b Me3Si cf3 〇 E.25b H 0 0 Cy6b Me3Si Cl 〇 E.30b H 0 0 Cy9b Me3Si cf3 〇 E.31b H 0 0 Cy9b Me3Si Cl 〇 E.32b H 0 0 CylOb Me3Si cf3 〇 E.33b H 0 0 CylOb Me3Si Cl 〇 E.40b H 0 1 Cyl4b H cf3 〇 E.41b H 0 1 Cyl4b H Cl 〇 E.42b :炔丙基 0 1 Cyl4b H cf3 〇 E.43b 丙二烯基 0 1 Cyl4b H Cl 〇 E.44b :炔丙基1 0 1 Cyl4b H c] 〇 E.45b 丙二烯基 0 1 Cyl4b H cf3 〇 E.46b Η 0 1 Cyl5b H cf3 〇 E.47b Η 0 1 Cyl5b H Cl 0 E.50b Η 0 1 Cyl7b H cf3 〇 E.5ib Η 0 1 Cyl7b H Cl 〇 E.52b :炔丙基 0 1 Cyl7b H cf3 〇 E.53b 丙二烯基 0 1 Cyl7b H Cl 〇 E.54b :炔丙基 0 1 Cyl7b H Cl 〇 E.55b 丙二烯基 0 1 Cyl7b H cf3 〇 E.56b Η 0 1 Cyl8b H Cl 〇 E.57b Η 0 1 Cyl8b H cf3 〇 E.58b Η 0 1 Cyl9b H cf3 〇 E.59b 1 Η 0 1 Cyl9b H C] 〇 46 200526672 E.60b :诀丙基 0 1 Cyl9b H 1 cf3 〇 E.61b 丙二烯基 0 1 Cyl9b H Cl 〇 E.62b :炔丙基 0 1 Cyl9b H Cl 〇 E.63b 丙二烯基 0 1 Cyl9b H cf3 〇 E.64b Η 0 2 Cyl7b H cf3 0 E.65b Η 0 2 Cyl7b H Cl 〇 E.78b Η 0 0 Cy23b Me3Si cf3 〇 E.79b Η 0 0 Cy23b Me3Si Cl 〇 E.80b Η 0 1 Cy24b H cf3 〇 E.81b Η 0 1 Cy24b H C1 〇 表21a提供83個式(I m)化合物,其中R1,m,η,Cy, R5,Y和X如表21a中之定義。 表21b提供36個式(I m)化合物,其中R1,m,η,Cy, R5,Y和X如表21b中之定義。
(CH2)m-C-(CH2)n-Y
表22a提供83個式(I mm)化合物,其中r1, Cy,R5,Y和X如表22a中之定義。 表22b提供36個式(I mm)化合物,其中R1, Cy,R5,Y和X如表22b中之定義。 47 200526672
(CH2)m-Cy-(CH2)n-Y
表23a提供83個式(I n)化合物,其中R1,!!!,n,Cy, R5,Y和X如表23a中之定義。 表23b提供36個式(I η)化合物,其中R1,!!!,n,Cy, R5,Y和X如表23b中之定義。
(CH2)m-Cy-(CH2)n-Y
表24a提供83個式(I nn)化合物,其中R1,m,η,Cy, R5,Y和X如表24a中之定義。 表24b提供36個式(I nn)化合物,其中Rhm^rMCy, R5,Y和X如表24b中之定義。
(CH2)m-Cy-(CH2)n-Y
表25a提供83個式(I 〇)化合物,其中R1,m,η,Cy, 48 200526672 R5,Y和X如表25a中之定義。 表25b提供36個式(I 〇)化合物,其中Rhm’n^Cy R5,Y和X如表25b中之定義。
(CH2)m-Cy-(CH2)n>Y
表26a提供83個式(I 〇〇)化合物,其中R1,m,n,Cy R5,Y和X如表26a中之定義。 表26b提供36個式(I 〇〇)化合物,其中R1,m,n,Cy R5,Y和X如表26b中之定義。
(loo)
(CH2)m-Cy-(CH2)n-Y S 表27a提供72個式(I p)化合物,其中m,η,Cy,R: P、7和Y如表27a中之定義。 表27b提供24個式(I p)化合物,其中m,η,Cy,R/ R7和Y如表27b中之定義。
(CH丄-Cy-(CH2)n-Y
49 200526672 表27a
Compound No. R2 m n Cy 1 一一 y R7 27.1 3-F 0 0 Cy2 Me3Si cf3 27.2. 4-F 0 0 Cy2 Me3Si cf3 27.3 5-F 0 0 Cy2 Me3Si cf3 27.4 6-F 0 0. Cy2 Me3Si cf3 27.5 3-F 0 0 Cy2 Me3Si cf2h 27.6 4-F 0 0 Cy2 Me3Si cf2h 27.7 5-F 0 0 Cy2 Me3Si cf2h 27.8 6-F 0 0 Cy2 Me3Si cf2h 27.9 3-C1 0 0 Cy2 Me3Si cf3 27.10 4-C1 0 0 Cy2 Me3Si cf3 27.11 5-C1 0 0 Cy2 Me3Si cf3 27.12 6-C1 0 0 Cy2 Me3Si cf3 27.13 3-C1 0 0 Cy2 Me3Si cf2h 27.14 4-C1 0 0 .Cy2 Me3Si cf2h 27.15 5-C1 0 0 Cy2 Me3Si cf2h 27.16 6-C1 0 0 Cy2 Me3Si cf2h 27.17 3-Br 0 0 Cy2 Me3Si cf3 27.18 4-Br 0 0 Cy2 Me3Si cf3 27.19 5-Br 〇 0 Cy2 Me3Si cf3 27.20 6-Br 0 0 Cy2 Me3Si cf3 27.21 3-Br 0 0 Cy2 Me3Si cf2h 50 200526672 27.22 4-Br 0 0 Cy2 Me3Si cf2h 27.23 5-Br 0 0 Cy2 Me3Si cf2h 27.24 6-Br 0 0 Cy2 Me3Si cf2h 27.25a 3-F 0 1 Cyl7a H cf3 27.26a 4-F 0 1 Cyl7a H cf3 27.27a 5-F 0 1 Cyl7a H cf3 27.28a 6-F 0 1 Cyl7a H cf3 27.29a 3-F 0 1 Cyl7a H cf2h 27.30a 4-F 0 1 Cyl7a H cf2h 27.31a 5-F 0 1 Cyl7a H cf2h 27.32a 6-F 0 1 Cyl7a H cf2h 27.33a 3-C1 0 1 Cyl7a H cf3 27.34a 4-C1 0 1 Cyl7a H cf3 27.35a 5-C1 0 1 Cyl7a H cf3 27.36a 6 - Cl 0 1 Cyl7a H cf3 27.37a 3-C1 0 1 Cyl7a H cf2h 27.38a 4-C1 0 1 Cyl7a H cf2h 27.39a 5-C1 0 1 Cyl7a H cf2h 27.40a 6-C1 0 1 Cyl7a H cf2h 27.41a 3-Br 0 1 Cyl7a H cf3 27.42a 4-Br 0 1 Cyl7a H cf3 27.43a 5-Br 0 1 Cyl7a H cf3 27.44a 6-Br 0 1 Cyl7a H cf3 27.45a 3-Br 0 1 Cyl7a H cf2h 27.46a 4-Br 0 1 Cyi7a H cf2h 27.47a 5-Br 0 1 Cyl7a H cf2h 27.48a 6-Br 0 1 Cyl7a H cf2h 27.49a 3-F 0 1 Cyl9a H cf3 27.50a 4-F 0 1 Cyl9a H cf3 27.51a 5-F 0 1 Cyl9a H cf3 51 200526672 27.52a 6孑 0 1 Cyl9a H cf3 27.53a 3-F 0 1 Cyl9a H cf2h 27.54a 4-F 0 1 Cyl9a H cf2h 27.55a 5-F 0 1 Cyl9a H cf2h 27.56a 6-F 0 1 Cyl9a H cf2h 27.57a 3-C1 0 1 Cyl9a H cf3 27.58a 4-C1 0 1 Cyl9a H cf3 27.59a 5-C1 0 1 Cyl9a H cf3 27.60a 6-Cl 0 1 Cyl9a H cf3 27.61a 3-C1 0 1 Cyl9a H cf2h 27.62a 4-C1 0 1 Cyl9a H cf2h 27.63a 5-C1 0 1 Cyl9a H cf2h 27.64a 6-C1 0 1 Cyl9a H cf2h 27.65a 3-Br 0 1 Cyl9a H cf3 27.66a 4-Br 0 1 Cyl9a H cf3 27.67a 5-Br 0 1 Cyl9a H cf3 27.68a 6-Br 0 1 Cyl9a H cf3 27.69a 3-Br 0 1 Cyl9a H cf2h 27.70a 4-Br 0 1 Cyl9a H cf2h 27.71a 5-Br 0 1 Cyl9a H cf2h 27.72a 6-Br 0 1 Cyl9a H cf2h 表27b
Compound No. R2 m n Cy Y R7 27.25b 3-F 0 1 Cyl7b H cf3 27.26b 4-F 0 1 Cyl7b H cf3 27.27b 5-F 0 1 Cyl7b H cf3 27.28b 6-F 0 1 Cyl7b H cf3 27.29b 3-F 0 1 Cyl7b H cf2h 27.30b 4-F 0 1 Cyl7b H cf2h 27.31b 5-F 0 1 Cyl7b H cf2h 52 200526672 27.32b 6-F 0 1 Cyl7b H CF2H 27.33b 3-C1 0 1 Cyl7b H cf3 27.34b 4-CI 0 | Cyl7b H cf5 27.35b 5-C1 0 1 Cyl7b H cf3 27.36b 6~C1 0 1 Cyl7b H cf3 27.37b 3-C1 0 1 Cyl7b H cf2h 27.38b 4-CI 0 1 Cyl7b H cf2h 27.39b 5-C1 0 1 Cyl7b H cf2h 27.40b 6-C1 0 1 Cyl7b H cf2h 27.41b 3-Br 0 1 Cyl7b H cf3 27.42b 4-Br 0 1 Cyl7b H cf3 27.43b 5-Br 0 1 Cyl7b H cf3 27.44b 6-Br 0 1 Cyl7b H cf3 27.45b 3-Br 0 1 Cyl7b H cf2h 27.46b 4-Br 0 1 Cyl7b H cf2h 27.47b 5-Br 0 1 Cyl7b H cf2h 27.48b 6-Br 0 1 Cyl7b H cf2h
表Fa係為表28a(當F為28時)及表29a(當F為29時)。 表Fa
Compound No. A m n Cy Y F.l nh2 0 0 Cyl Me3Si F.2 nh2 0 0 Cy2 Me3Si F.3 N〇2 0 0 Cy2 Me3Si F.4 oso2cf3 0 0 Cy2 Me3Si F.5 n=ch(c6h5)2 0 0 Cy2 Me3Si F.7 Br 0 0 Cy2 Me3Si F.l 8a νή2 0 0 Cy3a Me3Si F.l 9a N〇2 0 0 Cy3a Me3Si F.20a OS02CF3 0 0 Cy3a Me3Si F.21 νή2 0 0 Cy4 Me3Si 53 200526672
F.22 N02 0 0 Cy4 Me3Si F.23 OSO2CF3 0 0 Cy4 Me3Si F.24 nh2 0 0 Cy5 Me3Si F.25 N〇2 0 0 Cy5 Me3Si F.26 OS02CF3 0 0 Cy5 Me3Si F.27 N=CH(C6H5)2 0 0 Cy5 Me3Si F.28a nh2 0 0 Cy6a Me3Si F.29a N〇2 0 0 Cy6a Me3Si F.30a 〇s〇2cf3 0 0 Cy6a Me3Si F.31 nh2 0 0 Cy7 Me3Si F.32 N〇2 0 0 Cy7 Me3Si F.33 OS02CF3 0 0 Cy7 Me3Si F.34 n=ch(c6h5)2 0 0 Cy7 Me3Si F.35 nh2 0 0 Cy8 Me3Si F.36 N〇2 0 0 Cy8 —Me3Si F.37 OS02CF3 0 0 Cy8 Me3Si F.38 N=CH(C6H5)2 0 0 Cy8 Me3Si F.39a nh2 0 0 Cy9a Me3Si F.40a nh2 0 0 CylOa Me3Si F.41a N〇2 0 0 CylOa Me3Si F.42a OS02CF3 0 0 CylOa Me3Si F.43a N=CH(C6H5)2 0 0 CylOa Me3Si F.44 nh2 0 0 Cyll H F.45 N〇2 0 1 Cyil H F.46 nh2 0 1 Cyl2 H F.47 OS02CF3 0 3 Cyl2 H F.48 N=CH(C6H5)2 0 1 Cyl2 H F.49 nh2 0 1 Cyl3 H F.50 OS02CF3 0 1 Cyl3 H F.51 N-CH(C6H5)2 0 1 Cyl3 H 54 200526672 F.52a N〇2 0 1 Cyl4a H F.53a nh2 0 1 Cyl4a H F.54a 〇s〇2cf3 0 1 Cyl4a H F.55a n=ch(c6h5)2 0 1 Cyl4a H F.56a nh2 0 1 Cyl5a H F.57a OS02CF3 0 1 Cyl5a H F.58a N 二 CH(C6H5)2 0 1 Cyl5a H F.59 nh2 0 1 Cyl6 H F.60 os〇2cf3 0 1 Cyl6 H F.61 n=ch(c6h5)2 0 1 Cyl6 . H F.62a N〇2 0 1 Cyl7a H F.63a nh2 0 1 Cyl7a H F.64a OS02CF3 0 1 Cyl7a H F.65a n=ch(c6h5)2 0 1 Cyl7a H F.66a N02 0 1 Cyl8a H F.67a nh2 0 1 Cyl8a H F.68a OS02CF3 0 1 Cyl8a H F.69a n=ch(c6h5)2 0 1 Cyl8a H F.70a N〇2 0 1 Cyl9a H F.71a nh2 0 1 Cyl9a H F.72a OS02CF3 0 1 Cyl9a H F.73a N=CH(C6H5)2 0 1 Cyl9a H F.74 N〇2 0 0 Cyl Me3Si F.75 OS02CF3 0 0 Cyl Me3Si F.76 N〇2 0 0 Cy21 Me3Si F.77 νή2 0 0 Cy21 Me3Si F.78 N〇2 0 0 Cy22 Me3Si F.79 nh2 0 0 Cy22 Me3Si F.80a N〇2 0 0 Cy23a Me3Si F.81a nh2 0 0 Cy23a •Me3Si
55 200526672
F.82a nh2 0 1 Cy24a H F.83a N〇2 0 1 Cy24a H F.84a nh2 1 1 Cyl9a H F.85a 、T 1NU2 1 Cyl 9a T_T F.86a nh2 0 2 Cyl7a H — F.87a N〇2 0 2 Cyl 7a H F.88 OSO2CF3 0 1 Cy2 H F.89 n=ch(c6h5)2 0 1 Cy2 H F.90 nh2 0 1 Cy2 H 表Fb係為表28b(當F為28時)及表29b(當F為29時)。 表Fb ·
Compound No. A m n Cy Y F.18b nh2 0 0 Cy3b Me3Si F.19b N02 0 0 Cy3b Me3Si F.20b OS02CF3 0 0 Cy3b Me3Si F.28b nh2 0 0 Cy6b Me3Si F.29b N〇2 0 0 Cy6b Me3Si F.30b OS02CF3 0 0 Cy6b Me3Si F.39b nh2 0 0 Cy9b Me3Si F.40b nh2 0 0 Cyl Ob Me3Si F.41b N02 0 0 Cyl Ob Me3Si F.42b OS02CF3 0 0 Cyl Ob Me3Si F.43b n=ch(c6h5)2 0 0 Cyl Ob Me3Si F.52b N〇2 0 1 Cyl4b H F.53b nh2 0 1 Cyl4b H F.54b OS02CF3 0 1 Cyl 4b H F.55b n=ch(c6h5)2 0 1 Cyl 4b H F.56b nh2 0 1 Cyl5b H F.57b OS02CF3 0 1 Cyl5b H F_58b n=ch(c6h5)2 0 1 Cyl 5b H 56 200526672
F.62b N〇2 0 1 Cyl7b H F.63b νή2 0 1 Cyl7b H F.64b oso2cf3 0 1 Cyl7b H F.65b N=CH(C6H5)2 0 1 Cyl7b H F.66b N02 0 1 CylSb H F.67b nh2 0 1 Cyl8b H F.68b oso2cf3 0 1 Cyl8b H F.69b n=ch(c6h5)2 0 1 Cyl8b H F.70b N〇2 0 1 Cyl9b H F.71b nh2 0 1 Cyl9b H F.72b OS02CF3 0 1 Cyl9b H F.73b n=ch(c6h5)2 0 1 Cyl9b H F.80b N〇2 0 0 Cy23b Me3Si F.81b nh2 0 0 Cy23b Me3Si F.82b nh2 0 1 Cy24b H F.83b N〇2 0 1 Cy24b H
表28a提供90個式(Π a)化合物,其中A,m,η,Cy, 和Υ如表28a中之定義。 表28b提供34個式(Π a)化合物,其中A,m,η,Cy, 和Y如表28b中之定義。
(CH2)m-Cy-(CH2)n-Y
(Ha) 表29a提供90個式(Π b)化合物,其中A,m,η,Cy, 57 200526672 和Y如表29a中之定義。 表29b提供34個式(H b)化合物,其_ A,m 和Y如表29b中之定義。
(CH2)m-Cy-(CH2)n-Y A (Hb) 在所有的敘述中,所示之溫度為攝氏;『nmr』意為 核磁共振光譜;MS意、為質譜;除非㈣應之濃度以其他 單位表示,否則『%』為重量百公查. 里臼刀率,及旋光率係為在特 疋丨辰度,C,下由納線波長的角唐 心 π」月度,除非特別提及否則溶劑 為四氫咲喃。 下列簡寫使用於所有的敘述中: m. p.=嫁點 b*P·=沸點 s =單峰 br=寬峰 d=雙峰 dd=雙重雙峰 t ==三峰 q =四峰 m =多重峰 ppm =每百萬部分 qd=雙重峰之四峰 sext=六重峰 表30顯示表1至29仆人铷々、眩从w ^ 1匕σ物之遥錄熔點及使用cdci3 為溶劑(否則將特別提及;#存有混合溶劑則以例如 (CDChAVDMSO)表示)的選錄NMR數據,及特徵質譜訊 58 200526672 號(在所有案例中均未完全列出鑑定數據)。 表30 化合物號碼 】H=NMR數據:(ppm/波峰數/H數)或質譜訊號 m.p./( C) 1.3 107-111 1.4 0.0(s?9); 0.25(m5l); 0.7(m?l); 0.9(m?l); 1.7(m?l); 3.95(s?3); 6.85(t?l); 7.05(m?2); 7.2(m?2); 8.0(s5l); 8.1(d5l); 8.35(s?l). 94-95 1.4A-參見實施例7 0.0(s,9); 0.25(m,l); 0.7(m,l); 0.9(m,l); 1.7(m,l); 3.95(s,3); 6.85(t?l); 7.05(m?2); 7.2(m?2); 8.0(s?l); 8.1(d?l); 8.35(s5l). 油狀體 1.4B-參見實施例7 0.0(s?9); 0.25(m?l); 0.7(m?l); 0.9(m?l); 1.7(m?l); 3.95(s?3); 6.85(t,l); 7.05(m,2); 7.2(m,2); 8.0(s,l); 8.1(d,l); 8.35(s,l)· 油狀體
59 200526672
1.12 -0.18 (s,1.5); 0.0 (s,1.5); 0.0-0.2(m,l); 0.7(m,0.5);0.8(na,0.5); 0.95(m5l); 1.8(m,l); 2.3(m,l); 3.65(s?3); 4.2-4.35 and 4.8-4.95(m52); 5.85(s?0.5); 5.95(s?0.5); 6.9-7.6(m?5). 1.13 -0.18 (s,1.5); 0.0 (s,1.5); -0.1-0.2(m,l); 0.75(m,l);0.9 (m,0.5); 1.0(m0.5); 1.75(m,l); 3.7(s,3); 5.1(m,2); 5.75(s,0.5); 5.9 (s,0.5); 6.9-7.6(m,5); 7.85(t?l). 1.27 Mass spectrum: 378 (M+l; corresponds to M+H+); 441 (M+64; corresponds to M+MeCN+Na+) 1.60a 132-135 1.61a 117-119 1.63a Mass spectrum 416 (M+l; corresponds to M+H+). 1.78a 140 -141 1.84 119 -121 1.85 13M33 1.94a 74-77 1.96a 0.0(d,3); 0.4-2.1(m,13); 2.9(m,l); 3.9(s,3); 6.85(t,l); 7.1-7.2(m?2); 7.3(m?l); 7.6(br.l); 7.8(br.l); 8.0(br.l) 1.98a 0.0(s,3); 0.05(s,3); 0.45(m,2); 0.75(m,2); 1.2-2.0(m,5); 2.55(d,2); 4.0(s,3); 6.9(t,l); 7.1-7.3(m,3); 7.9-8.0(m,br,2); 8.1(br.s,l) 3.3 0.0(s,9); 0.22(m,l);0.7(m,l); 1.8(m,l); 7.15(m,2),7.3(m,l), 7.45(m,l); 8.2(d,l),8.3(d,l); 8.55(broad s + m,2). 5.3 61-64 5.60a 118-119 13.3 98-99 21.3 0.0(s,9); 0.22(m,l);0.9(m,2); 0.9(m,l); ].7(irU); 3.72(s,3); 6.95(s,l); 7.05(m,2),7.2(m,l),7.3(s,l); 8.05(broad s,1); 8.15(d,l). 21.51a 88-92 28.2 -0.1(m,l); 0.0(s,9); 0.75(m,2),1.6(m?l); 3.95(broad,2); 6.65(m,2);7.0(m,2). 60 200526672 28.4 0.0(s,9); 0.1(m,l); 0.9(m,2); 2.0(m,l); 6.9(d,l); 7.2(m,3). - 28.5 0· 0(s,9); 0.1(m,l); 0.9(m,l); l.l(m5l); 2.0(m,l); 6.5(m,l); 1 6.9(m,3); 7.2(m?2); 7.3(m?3); 7.5(m?3); 7.9(d?2). 28.24a 質譜:234(M+1 ;相當於M+H+) ; 275(M+42 ;相當於 M+MeCN+H+)· ^ ^ 28.63a 0.0(s,3); 0.1(s,3); 0.45(d 之 t,l); 0.7(t,2); 0.9(m,l); 1.2(m,l); 1.5(m?l); 1.85(m?l); 2.1(m?l); 2.5(m5l); 3.65(bs?2); 6.65(d?l); 6.75(t5l); 6.95(t,l); 7.1(d5l). —— 28.82a 0.0(s,6); 0.6(m,2); 1.8(m,2); 2.2(m,2); 3.9(極寬之 s,2); 5.6(M); 6.6(m,2); 6.85(m,l); 6·95(χη,1)· '-Ss 28.83a 0.0(s,6); 0.6(m,2); 1.8(m,2); 2.2(m,2); 5.4(s,l); 7.15-7.8(m,4). 28.86a -0.0(s,6); 0.6(m,1.5); 0.4-2.1(m,13); 2.6(m,l); 3.4(br,2); 6.6(d,l); 6.7(t,l);6.9(t,l);7.1(d,l). '—— 28.88 黃色油狀靜 28.89 質譜·· 384(M+1 ;相當於 M+H+). ----— 28.90 質譜:220(M+1 ;相當於 M+H+). ~ —-- 本發明化合物可依據下列之反應方案製備,其中若_ 特別提及,每種變數的定義一如上文式(I)化合物之定義。 亦可有數種不同方法可用於製備式(I)化合物。
方法A 式(I)化合物之製備可藉由式(Π)化合物〔其中A NH2,NHCH(O),選擇性經取代的(CV4)烷基C(=〇)NH或 選擇性經取代的((^_4)烷基OC( = 0)NH〕與式^ 化合物反應〔其中^為Cl·4烷基〕,反應在強鹼下〔例如 NaH或穴曱基二石夕氮烧納〕進行於無水極性溶劑〔較佳為 THF〕及溫度在-丨至溶劑沸點之間〔較佳為環境溫度〕。 於J.Wang等人之文獻〔synlett 2001,1485〕提供了詳細 的相類似製備方法。當A為NHCH(O),選擇性經取代的 烧基C( = 〇)NH或選擇性經取代的((γ4)烷基0C卜g〇nh, 且欲得到其中R】為Η之式⑴化合物時,則必需接著依據 61 200526672 下文之方法E進行水解。 方法1 上文二方去物之製備可藉由式(π)化合物〔其中A為 上文之方法八中 ^ 〔其中R,,為土 、式H叫=〇)〇R”化合物反應 烷基〕,反岸進二於基’例如⑴6…或0C(=0)Ck4 曱烧,二錢::惰:有機溶劑〔例如乙酸乙醋,二氯 之間〔較佳為環境溫度〕=二在 存有活化劑〔例如BQp⑴/ 4 H’収應係進行於 無機碳酸鹽或碳酸:Γ:兩當量的驗〔例如三級胺, 烧基C(=0)NH或、^心_ CH(〇)、選擇性經取代的(C】-4) 擇性經取代的烷基〇 則使用強鹼,例如NaH A 匕 κ川Η日守
NaHu基二錢㈣〕。若欲得到 ’’’、之式(1)化合物時,則必需接著依據下文之方 法E進行水解。
方法C
式(I )化合物〔其中R1為上文中之定義但並非為氫〕 之製備可藉由式(1)化合物〔其巾R,為氫〕與式R] L、 ::反應〔其巾R〗為上文中之定義但並非為氫;及L1為 方基約如' Br ’ 1 ’磺酸鹽(例如甲磺醯酸鹽戋田楚 石黃酸鹽)或0C(0)C1.4烧基〕,反應進行於溶劑中〔例如: 化溶劑(如二氯甲燒),⑽,乙酸乙g旨,DMF或甚至水(做為 兩相混合#’選擇性地存有相轉移催化劑如四丁基硫酸氣 銨)〕並存有鹼〔例如三級胺,鹼性碳酸鹽’鹼性碳酸氫鹽7 鹼性氫氧化物或NaH;但當1^為〇(c〇)Ci_4烷基時則;能 62 200526672 在無需鹼下簡易地加熱〕。 方法互 式(I )化合物之製備可藉由式(Π )化合物〔其中a為 鹵素,較佳為溴或碘〕與式Het-C(=〇)NH2化合物反鹿, 反應於存有Cu(I)化合物及非質子溶劑下〔例如環峻,如 二噁烷〕進行於提高的溫度且較佳為迴流。較佳者為cw 之使用為相對於式(Π)化合物之2%至1〇〇%莫耳/莫耳 並存有1,2-二胺(例如1,2-二胺基環己烷或乙烯二胺)做為 配位體形成物質及至少一當量之鹼(例如鹼性碳酸鹽或鹼性 磷酸鹽)。A. Klapars 等人於 J· Αιη· chem· Soc. 7727(2001)的文獻提供了詳細的相類似製備方法。
方法E 式(I )化合物〔其中R1為Η〕之製備可藉由式(j )化 合物〔其中R1為上文中之定義但並非為氫〕以酸性或驗性 水解。為此目的,該化合物在較佳為可與水混合的適當溶 劑中〔例如THF,二噁烷,低碳醇或水本身〕,於環境溫 度或提高溫度下以水性酸或鹼處理,例如HC1,HBr或有 機性氫氧化物〔例如氫氧化鈉、鉀、_或鎖〕。
方法F 式(I )化合物〔其巾R1為Η〕之製備可藉由式(n )化 合物〔其中A為N^C^5)2〕依據例如由Ahman等人 述於 Tetrahedron Letter 38,6363〇997)之方法,並依據方 法A或方法Μ A轉換成顺2 ’其中較佳為無需分離或純 化中間體。 63 200526672 為上文中之定義),其中在 ,已揭示於該文獻内。 許多式(m)或(ιν)化合物(r3 苯或噻吩環上並未有額外取代基
(III)
R …w μ喝虽吕跪性質之A,道
式叫或(IV)化合物中,並在必要時轉換成所 二另外地且為較佳地’式⑴化合物的 = 中製備式(m)和(IV)化合物相類 使用與文 已在所需位晉卜呈古、在A 具中之起始物 在所而位置上具有適當取代基A’;這些 a)和(IV a)。通常盆中之;5 _片^ 奶料之為( 外的取代“,來;:改= 化合物所述之習知方法轉換成二)依據式⑶ 列方案且將進一步於下文中描述:…成形態述於-
Ilia.
與製備III相類似之方法
lla
lla
64 200526672 步驟1 : 部分使用於製備式(m )化合物的適當方法可利用適當 起始物質在修正的條件下用來製備式(na,)化合物,並係 述於下列文件·· 有機化學期刊(J· 〇rg. Chern.)65,8919(2000);四面體 (Tetrahedr〇n)49,8487(1993);有機化學期刊 51, 2206(1986);有機化學期刊 56,3 1〇9(1991); Acta chem Scand. 53 ’ 493(1999);美國化學學會期刊123,i〇899(2〇〇1);有 鲁 機通訊(Org. Lett. )4,2225(2002);四面體 57,2847(2001); 四面體通訊42,6137(2001);四面體通訊36,3119(1995); EP 6965 92; EP 713878; FR 2689893;日本化學學會會報(Bull·
Chem. Soc. Jpn.) 64,1461(1991) ; W0 9214692 ;有機化學 期刊 67 ’ 6869(2002);殺蟲劑科學(pesticide science) 52, 138(1998) ; Izv. Akad. Nauk,Ser· Khim. 1996,955 ; 1995, 2475);四面體通訊 33 ,2295(1992);有機金屬 (Organometallics) 1 1,1428(1992); 10, 528(1991); Ann· Chem· · 1979,1915 ; J. Orgmet. Chem· 341,133(1988) ; Zeitschrift f· Anorg· Allg· Chern· 459 5 37(1979);四面體通訊 22, 4449(1981) ; US 3125637 ;有機化學期刊 65,3 135(2000)。 A’為如上文中所定義之A基團,或A的前驅物基團, 其可與步驟1的反應條件相容且可藉由習知的化學方法轉 換成A。尤其有價值的前驅物基團為自由形式且為經保護 之OH和經保護之胺基。苯酚和苯胺的較佳保護基團參考 65 200526672 文獻示於例如T.W. Green和P.G.M· Wuts,有機合成中的 保護基第三版,p.5 03-614( Wiley 1999)。 步驟2 : 依據A’的性質,式(Π a’)化合物可變換成式(n a)化合 物(其中A = NH2)〔例如催化性氫化作用或化學反應(a,為 硝基)或去保護作用(A’為經保護胺基)〕。式(jja)化合物(A = 〇S〇2CF3)的製備可藉由將經保護〇H進行去保護作用(如 果A’為經保護OH)並將所得到之式(&,)化合物(a = 〇H) 利用三氟甲基磺酸酐和適當的鹼轉換成三氟曱基磺酸鹽 鲁 (triflate)。式(na)化合物(A為〇s〇2cF3或鹵素)可在進一 步的步驟中變換成式(Ua)化合物(A=Nh2),所使用之方法 有J. Ahman等人述於四面體通訊38, 6363〇997)和χ h仙% 等人述於有機通訊(0rg.Lett〇i,3417(2〇〇1)及於本文中所 引用之參考文獻。 令人驚訝者為,
的絕佳活性範圍。
同時亦可保護後 同作用植物或植物部位(果 根)的有害生物,同睹 66 200526672 續長成的植物部位免於植物病原微生物感染。 式(I)化合物亦可能使用為種衣劑來處理植物繁植物 負’特別是種子(果實,塊莖,種粒)和植株插穗(例如米), 保護其免於真菌感染以及免於生成於土壤中的植物病原性 真菌感染。 本發明化合物可進一步使用於控制在相關領域之真 菌,例如在加工材料之保護包括木料和與木料相關的加工 產品、食物儲藏、衛生保健管理等方面。式⑴化合物可有 效地阻抗下列綱分類的植物病原真菌:不完全真菌綱(例如 φ 葡萄菌屬(Botrytis) ’稻瘟菌屬(pyricularia),長蠕孢菌屬 (Helminthosporium),鐮刀菌屬(—μ·),腐爛菌屬 (Sept〇ria) ’尾形孢子菌屬(Cerc〇sp〇ra)和又鏈孢子菌屬 (Altemaria))的擔子菌綱(例如絲核菌屬(Rhiz〇ct〇nia),半平 菌屬(Hemileia),柄鏽菌屬(Puccinia))。除此之外,它們亦 可有效地阻抗囊菌(八%〇11^(^“)綱(例如彎脈菌屬(Benturia) 和紅管菌屬(Erysiphe),球足菌屬(Pod〇sphaera),褐腐病菌 屬(Monilinia) ’ 角菌屬(Uncinula))和卵菌綱(〇〇mycetes)(例 φ 如疫菌屬(Phytophthora),腐霉菌屬(Pythium),單軸霉菌屬 (Plasmopara))。已觀察到其等具有極佳的活性可阻抗白粉 菌(紅管菌屬)。此外,新穎的式I化合物可有效地阻抗植 物病原細菌和病毒(例如阻抗黃單膜菌屬(Xanth〇m〇nas spp·),假單胞菌屬(Pseudomonas spp.),梨火病病菌(Erwinia amylovora)以及阻抗煙草錦紋病毒)。 在本發明範圍中,可受到保護的標的農作物典型包含 67 200526672 下列植株種類:縠類(小麥,大麥,裸麥,燕麥, 高梁和相關物種);甜菜(食用甜菜和飼 :、二米’ 果和軟果r葙® -I ^ a j ^果’核 果"人果(頻果,梨,李,桃,杏仁’櫻 和黑莓豆科植物(豆,爲豆,f宛豆,大草母後盆子 菜,芥太,堀㊉ )’油性植物(油 可豆,落花生二,撖欖,向曰葵’椰子q麻油植物,可 亞广/’s瓜植物(南瓜’黃瓜,甜瓜);纖維植物(棉 麻,麻,黃麻);柑橘果實(柳撥,择樣 馬鈴著,、-椒”樟科(鱷梨,掉腦)或例如煙草::加: Ή,甘薦,茶,胡椒,藤,蛇麻草,香 膠的植物,以及園藝植物。 、 方技=合物係以未改質形式使用,或較佳與習用於配 Π二 同使用。有關此點,t們可方便地以習知 乂 可礼化/辰縮液,可塗覆糊,可直接喷霧或稀釋 浴液:稀釋乳液,可濕性粉末,可溶解粉末,塵劑,顆粒, :在例如聚合性物質内。組成物類型,應用方法如 喷霧、務化、撒粉、散射、塗佈或濟鑄係依據所欲達到之 目的以及所在環境而選擇。此等組成物亦可進一步含有輔 劑、’例如穩定劑,抗發泡劑,黏度調節劑,黏合劑或增黏 M]以及肥料、极營養施體或得到特別效果的其他配方。 適當的載體和輔劑可為固體或液體且為有用於配方技 術之物質,例如天然或再生的礦物質、溶劑、分散劑、滿 潤劑、增黏劑, _ . θ稠劑,黏合劑或肥料。這些載體例如述 於 WO 97/33890。 68 200526672 式(I)化合物通¥以組成物形式使用,並且係與其他化 合物同時地或依序地施加至農作物區域或欲處理的植物 上。這些其他化合物可例如為肥料或微營養施體或其他可 影響植物成長的配製物。它們亦可選自除草劑和殺蟲劑、 殺真菌劑、殺細菌劑、殺線蟲劑、殺軟體動物劑或數種此 類配製物的混合物,如果需要時可共同與其他載體、界面 活性劑或習用於配方技藝之加強應用性輔劑。
式(I)化合物可與其他殺菌劑混合,在一些案例中可造 成料想不到的協同活性。混合成分中特別佳者為卩比略類, 例如氧環唑(azaconazole),BAY 14120,比多農(bitertan〇1), 溴克座(bromuconazole),環克座(cyproconaz〇le),待克利
(difenoconazole),達克利(diniconazole),依普座 (epoxiconazole),芬克座(fenbuconazole),氫喹 口坐 (fluquinconazole),護矽得(flusilazole),護汰芬(fiutriaf〇1), 菲克利(hexaconazole),依滅列(imazaiii),易胺座 (imibenconazole),種菌唑(ipconazole),經菌嗤 (metconazole),米可甫坦尼(mycolobutanil),披扶座 (pefurazoate),平克座(penconazole),比芬諾(pyriferiox), 撲克拉(prochioraz),普克利(propiconazoie),氮氟嗤 (simeconazole),得克矛 J (tebuconazole),四克禾j (tetraconazole),三泰芬(triadimefon),三泰隆(triadimenol), 赛福座(triflumizole),環菌唾(triticonazole);。密唆基卡賓 諾(carbinole)類,例如。密咬醇(ancymidol),芬瑞莫 (fenarimol),尼瑞莫(nuarimol) ; 2-胺基嘧啶類,例如布瑞 69 200526672 莫(bupirimate) ’ 二曱。密吩(dimethirimol),依瑞莫 (ethirimol);嗎啉類,例如十二環嗎啉(d〇dem〇rph),芬波 皮、’丁(fenpropidine),芬普福(fenpr〇pim〇rph),史拜羅沙明 (spiroxamine),三得芬(tridem〇rph);苯胺基嘧啶類,例如 赛普洛(cyprodinil),滅派林(mepanipyrim),派美尼 (pyrimethanil);毗咯類,例如拌種咯(fenpicl〇nil),護汰寧 (fludioxonil),本基酿胺類,例如苯達樂(benaiaXyi),咲霜 靈(furalaxyl),滅達樂(metaiaXyi),滅達樂,呋酿胺 (ofurace),歐殺斯(〇XadiXyi);苯並咪唑類,例如免賴得 (benomyl) ’ 貝分替(carbendazim),口米菌威(debacarb),麥 穗 f (fuberidazole) ’ 腐絕(thiabendazole);二甲醯胺,例如 克氯得(chlozolinate),二克氯得(dichlozolinate),依普同 (iprodione) ’ 米可諾玲(myclozoline),撲滅寧 (procymidone) ’免克寧(vinci〇z〇iine);緩醢胺類,例如萎 鐘篮(carboxin) ’甲咲酿苯胺(fenfuram),福多寧 (flutolanil),滅普靈(mepronil),嘉保信(oxycarboxin),赛 氟滅(thifluzamide);胍類,例如克熱淨(guazatine),多寧 (dodine) ’伊米歐達丁(iminoctadine);嗜球果傘素類 (strobilurines) ’ 例如亞托敏(azoxystrobin),克收欣 (kresoxim-methyl),苯氧菌胺(metominostrobin),SSF -1 29, 三氟敏(trifloxystrobin),啶氧菌酯(piCOXyStrobin),BAS 5 00卩(提議名稱百克敏(1^1^(:1〇价〇|^11)),3人8 520;二硫胺 基甲酸酯類,例如富爾邦(ferbam),鋅锰乃浦(mancozeb), 猛乃浦(maneb),免得爛(metiram),甲基鋅乃浦(propineb), 200526672 得恩地(thiram),鋅乃浦(zineb),福美鋅(ziram) ; N鹵甲 基硫四氳-鄰苯二甲醯亞胺類,例如四氯丹(captaf〇1),蓋 普丹(captan),益發靈(dichl〇nuanid),氟氯菌核利 (fluoromides),福爾培(f0lpet),甲基益發寧(t〇lyfluanid);
銅-化合物’例如波爾多(Bordeaux)混合物,氫氧化銅,氯 氧化銅,石瓜銅自文,氧化亞銅,代森猛銅(manc〇pper),心經 基喹啉-銅;硝基酚-衍生物,例如白粉克(din〇cap),酞菌 酯(nitrothal-isopropyl);有機-P-衍生物,例如護拉松 (edifenphos),異稻瘟淨(iprobenph〇s),亞賜圃 (isoprothiolane),米松(phosdiphen),白粉松(pyrazoph〇s),
脫克松(tolclofos-methyl);各種之其他類,例如艾西苯諾 爾(acibenzolar)-S-甲基,敵菌靈(aniiazine),苯噻菌胺 (benthiavalicarb),保米黴素(blasticidin-S),來蟎猛 (chinomethionate),二氣甲氧苯(chloroneb),四氯異苯腈 (chlorothalonil),喜佛分拿米(Cyflufenamid),克絕 (cymoxanil),二氯苯醌(dichlone),達滅淨(diclomezine), 大克爛(dicloran),代艾索芬卡(diethofencab),達滅芬 (dimethomorph),SYP-LI90(提議名稱:氟嗎啉(flumorph)), 腈硫 (dithianon),艾沙伯辛(ethaboxam),依得利 (etridiazole),凡殺(famoxadone),口米唾菌酮(fenamidone), 禾草靈(fenoxanil),三苯錫(fentin),富米綜(ferimzone), 扶吉胺(fluazinam),氟硫滅(flusulfamide),環 gi 菌胺 (fenhexamid),福赛得(fosetyl-aluminum),殺紋寧 (hymexazol),丙森鋅(iprovalicarb),IKF-916(赛座滅 71 200526672 (cyazofarnid)) ’ 嘉賜徽素(kasugamycin),滅速克 (methasulfocarb),美沙芬歐(metrafenone),尼可比芬 (nicobifen),賽克隆(pencycuron),熱必斯(phthalide),保 粒黴素(polyoxins),撲殺熱(pr〇benaz〇ie),伯朋諾卡 (propanocarb) ’ 百快隆(pyroquiIon),快諾芬(quinoxyfen), 五氯硝基苯(quintozene),硫,氧化疊氮,三環毗咯,賽福 寧(triforine),維利黴素(validamycin),羅醯胺 (zoxamide)(RH7281) °
式(I)化合物,或含有至少其中一個化合物之農化組成 物,的較佳W用方法為葉式施用。施用的的頻率及施用比 率則依受相對應病原感染的風險而定。然而,式J化合物 亦可藉由將植物所在地浸潤於液態配方中再經由土壤由根 滲透至植物(系統作用),或藉由將固態形式,例如顆粒形 式,之化合物施加至土壤(土壤施用)。在水稻作物中此類 顆粒可施加至充滿水的水田中。式J化合物亦可施用(涂覆)
广上’其係藉由將種子或根莖浸潰至殺菌劑的液態配 製物中或以固態配製物塗覆。 丄 ,6 π叭、i )化合物〜組力乂初J及選; 存有之固態或液態輔劑可使用習知方法製冑,蛊型地: 化合物與增量劑’例如溶劑、固體載體及視情況選用: 面活性化合物(界面活性劑),完全混合及/或研磨。 農化配製物通常含有U化合物為由〇1纟9 :較佳由°,1至95重量%,固態或液態輔劑為由99 9 j 重ϊ%且較佳由99·8至5重量%, ·- 里彳及界面活性劑為由〇 72 200526672 25重夏%且較佳由〇·1至25重量%。 有利者為施用比率通常為每公(ha)由5g至2kg之活性 成刀(a i·)較佳為由1 〇g至1kg a.i./ha,最佳為由20g至600g a.i./ha。當做為種子浸潤劑使用時,一般的劑量為每公斤 種子使用l〇mg至lg之活性物質。 然而較佳為將商用產品配製成濃縮物,消費者通常是 使用稀釋配製物。 【實施方式】 下列非限制性實施例係更詳細地說明上述之本發明。 實施例 該實施例係說明化合物號碼28.8;3a、2S.63a和丨61a 的製備方法。 盘二甲基-3-(2’-硝基)苯里己基_2ί化 合物 28,83a1 2-石肖基苯基乙炔(依據合成(Synthesis) 1980,627之方
法製備)(2Sg),1,1-二甲基-1-矽雜環己烷(219ml)和 PdCl2(Ph3P)2(9.5g)在450ml無水甲烷中於氮氣圍下迴流3 小時。冷卻至室溫之後將溶劑蒸發移除,殘餘物(5 1.8g)經 由1.3kg之矽膠進行色層分析(沖提液:己烷··乙酸乙醋: 39:1)。分離出橄攬綠顏色的油狀物(19.9g),其含有6〇% 之化合物28.83a(依據nmr)。此物質可直接使用至下一個 步驟。 步驟Β: 1·1-二曱基-3- (2’-胺基)苯暮己美化 合物 28.63a] 73 200526672 下在THF中由鈀(碳 ,蒸發出溶劑及經矽 於步驟A之產物在大氣壓及室溫 上之10%)進行氳化。過濾出催化劑 己烷:乙酸乙酯·· 19:1)生成化合物 膠之色層分析(沖提液: 28.63a (5.75g) 〇 兔驟C :化合物號碼i.6ia 將化合物號碼28.63a(0.17g)溶解於THF(5ml)。在冰的
冷卻下加人N-T基-3-二氟甲基_4·氯幾基_〇比。坐(〇」5g),然 後加入毗啶(0.062ml)。所得到之白色懸浮液攪拌隔夜再 將之倒至水内,經乙酸乙酯萃取後以硫酸鈉乾燥。蒸發移 除溶劑且殘餘物(0.3g)經矽膠進行色層分析(沖提液:己烷: 乙酸乙酯:2:1)生成化合物號碼,熔點為ιΐ7_ 119〇C。 可使用相類似的反應順序〔但使用丨_甲基_ ^乙基-矽 雜環丁烷或1-甲基-1-乙烯基-矽雜環丁烷取代二甲基_ 1-矽雜環丁烷起始〕進行化合物號碼28.87a、28 8仏和l 96a 之製備。 實施例2 該實施例係說明化合物號碼28.82a和1.94a的製備方 法0 ^AULL-二甲基-3-(2’-胺基丄 il# 28.82a1 將得自實施例A之產物(1.5g)溶解於乙醇(5〇ml ; 5〇 體積%)並於其中加入粉末化鐵(1.5§)。所得到之懸浮液加 熱至迴流。在此溫度下,溶於乙醇(3.5ml,50體積%)之 74 200526672 HCl(0.3 5ml,2N)在超過i〇分鐘下加入,並將所得到之混 合物迴流隔夜。冷卻至室溫後,過濾懸浮液,以碳酸氫鹽 中和、經乙酸乙酯萃取及以硫酸鈉乾燥。將溶劑蒸發移除, 經矽膠進行色層分析(沖提液:己烷:乙酸乙酯:9:1)得到化 合物 28.82a(〇.14g)。 亦分離得到2-胺基苯乙烯(〇.06§)和丨_烯丙基__二曱基 曱矽烷基·2-(2,-胺苯基乙烯(0el2g)為副產物。 匕合物號礁1.94a 此化合物係依據實施例1之步驟C,製備自丨,^二曱 馨 基-3_(2’-胺基)苯基-矽雜環己烯-2〔化合物28.82a〕(〇 12g) 和N-甲基-3-三氟曱基氯羰基_吡唑(〇12§)。產率為 之灰白色結晶,熔點為74-77°C。 實施你 該實施例係說明化合物號碼28·4、28·5、28·2和5·3 的製備方法。 ^^1^_^-1-(2,:三氟甲基磺醯氫甚苹其19_二甲早 甲矽炼基丙烷「化合物28.4 Ί · 反式·1-(羥苯基)-2-三甲基甲矽烷基環丙烷(2.9g)〔依 據有機通訊4, 2225(2002)之方法製備〕溶解於毗啶(15mi) 中並在〇-5°C下以三氟甲基磺酸酐(2.55ml)處理。混合物先 在此溫度下攪拌90分鐘然後再於室溫下攪拌9〇分鐘。以 水/月洗,經乙酸乙酯萃取,再經硫酸鈉乾燥,移除溶劑及 經矽膠進行色層分析(沖提液:己烷:乙酸乙酯:19:1)生成 化合物28.4 (4.4g),其可直接使用至下一步驟。 75 200526672 亞胺基_茉^^ 甲基甲逆^基」^— 無水THF(40mi)小心地藉由通入氮氣ls分鐘進行除 軋。在虱《I圍下’依序地加入二乙酸鈀(〇 i5g)、外消旋性 BINAP(0.65g)和一苯甲酮亞胺(2 3mi)。在室溫下授拌 刀鈿之後,加入奴酸鉋(5 · i g)且混合物在迴流下攪拌隔夜。 冷卻之後,將懸浮液倒入水(8〇ml),以乙酸乙酯萃取兩次, 經硫酸納乾燥後移除溶劑。殘餘物(6.05g暗綠色油狀體)經 石夕膠進灯色層分析(沖提液:己烧:乙酸乙酉旨:m)生成化 合物28.5 (3.55g),其可直接使用至下一步驟。 之驟C ·么立二胺基苯某V2-三曱基曱矽、 否烷〔化合物28.? 將化合物28.5(3.5g)溶解於甲醇(95ml),然後依序加 入乙酸鈉(1.9g)和羥基胺氫氣酸鹽(1.2g)。在室溫下攪拌75 刀^之後,將混合物倒入氫氧化鈉(5〇〇ml,〇 1N水溶液), 、乙S文乙S曰萃取兩次。如步驟B所述地純化並將半固態殘 餘物(3.8g)經矽膠進行色層分析(沖提液:己烷:乙酸乙酯: 9·1)彳于到化合物28.2 (1.9g)為油狀體。 該化合物之製備如同於實施例丨之步驟c,並得自反 式胺基_笨基)_2_三曱基曱矽烷基-環丙烷〔化合物 28.2〕(〇.25g)& 2_曱基_4_三氟甲基_4_氯羰基噻唑㈧.28g)。 產率為0.45g之灰色結晶,熔化於61_64〇c。 賁施例4 76 200526672 該實施例係說明化合物號碼3·3的製備方法。 將Ν-甲基-4·三氟曱基_3-吡咯羧酸(〇_24§)、化合物 28.2(0.25g)和三乙胺(〇 34ml)溶解於無水二氯甲浐 (25ml),用冰冷卻且以雙氧基-3-噁唑烷基_膦酸氯化物 (〇.31g)處理。所得到的懸浮液在冰浴内攪拌丨小時再於室 溫下攪拌15小時。然後混合物以乙酸乙酯(25〇mi)稀釋, 再加入飽和的碳酸氫鈉溶液(丨25ml)。分離出有機相且以硫 酸鈉乾燥。移除溶劑並將殘餘物(〇_45g之黃色油狀體)經矽 膠進行色層分析(沖提液:己烧:乙酸乙醋:2:丨)生成化合物 _ 2·3(0.2g)為油狀體。 實施例5 該實施例係說明化合物號碼1 · 84的製備方法。 使用與Sonagashira所述(合成i980,627)之相似方法, 由2-胺基-4’-溴聯苯製備而得胺基_(4,_三甲基曱矽烧基 乙炔基)聯苯。該化合物使用述於實施例1步驟c之類似 方法與N-甲基-3-二氟曱基-4-氯魏基-p比唾反應,得到酿胺 (m.p.l51-153°C )。將此醯胺(〇.5g)溶解於 THF(l〇ml),且在 _ 室溫和大氣壓下由鈀(O.lg ;碳上之1〇%)進行氫化。過濾 反應庇合物而移除如化劑,及蒸發出溶劑。將殘餘物(〇 · 5 2 g 之灰色晶體)經矽膠進行色層分析(沖提液:己烷:乙酸乙 酯:2:1)生及化合物 。 實施例6 該實施例係說明化合物號碼1 ·丨2和1 ·丨3的製備方法。 化合物號碼1 ·4( 1 g)〔使用與實施例3步驟〇的相似方 77 •200526672 法製備並使用N-甲基-3-二氟甲* / 土、'氣羰基毗唑做為化合 物號碼28.2的偶合共用劑〕被 鮮於無水丁HF(50ml)並小 心地加入氫化鈉(0.13g在礦物油中 、 T的55%懸浮液)。反鹿 混a物在環境溫度下攪拌2 · 5小時。缺 . 守。然後加入炔丙基溴 (0.23g)及將反應混合物在氮氣圍 ^ Γ償拌隔仪。所得到之縣 浮液以乙酸乙酯(200ml)稀釋並以大、、主 心 ^ 水/月洗,經硫酸鈉乾燥然 後蒸發移除溶劑。殘餘物經石夕膠淮 /胗進仃色層分析(沖提液··己 燒··乙酸乙酯·· 2··1)生成化合物铼m , 珉化口物麵和化合物號 碼1.13(0.52g),兩者均為淺黃色油狀體。 實施例7 該實施例係說明化合物铗踩,/ ^ 法 口物唬碼丨·4的純對映體製備方 消旋性之化合物號碼Μ〔製備方法參見實施例6〕(每 次注射為(Mg)由製備性掌性Ηριχ管柱分離出,所使用之 條件如下:管柱:ChiracelTM〇D (DaiceiTM) “Μ ;沖提液·· 正-己烷/2-丙醇70:30 ;流量:3〇 ml/min。經手動分離2個 波峰之後溶劑被蒸發掉。殘餘物溶解於二異丙基醚中並過鲁 濾^蒸發移除溶劑而得到純的對映體;化合物號碼14A〔旋 光率.-89.i(c = iz.4g/i)〕及化合物號碼14B〔旋光率: + ,兩者均為無色油狀體。 式丄丄_1化合物的配方實施.例 式(I)化合物之配方,例如可乳化濃縮液、溶液、顆粒、 塵知和可潤濕粉末’其製備方法之操作步驟述於w〇 97/33890 〇 78 ,200526672 生物性實施例:殺詰劑作用 作用 貫遞,.例B-1 :阻抗隱匿柄鐘_菌/小__^^小麥的華」、之 1星期齡的阿玲娜(Arina)品種小麥植株在喷霧室内以 配製成的測试化合物(〇 ·02 %活性成分)處理。施加一天 後’小麥植株藉由喷霧孢子懸浮液(lx 1 〇5夏孢子/毫升)至則 試植株上進行接種。在20°C及95%相對濕度下2天的培 育期後’將植株留存在2(TC及60%相對濕度的溫室中°8 天。接種10天後評估罹病度。 使用化合物 1.3、1.4、1.60a、1.61a、1 84 《,十 1、5.3 和 21.3 可實質完全地避免感染(0-5%感染率)。 室M^-又:阻抗白叉絲單嚢殼 之作用 内 5星期齡的麥金塔(McIntosh)品種蘋果幼苗在喷霧室 以配製成的測試化合物(〇·〇2%活性成分)處理。一 ^ 大之後, 完成施加的蘋果植株藉由將感染蘋果白粉病的植株在測試 植株上方搖動進行接種。在22t及60%相對濕度下12 的培育期後,在14/10小時(光/暗)的光照處理下評估罹病
度。 A 3和21.3均 化合物 1.3、1.4、1.60a、l_61a、1.84、 顯現出高效率(< 20%感染率)。 t施例B-3 :阻抗白粉病菌/大來Γ女 1 1星期齡的瑞金娜(Regina)品種大麥植株在喷霧室内以 79 200526672 配製成的測試化合物(0.02%活性成分)處理。施加—天之 後,大麥植株藉由將感染白粉病的植株在測試植株上方搖 動進行接種。在2(rc/18t;(日/夜)及60%相對濕度下6天 的培育期後,在溫室中評估罹病度。 化合物1.3、1.4、Uh、uu、丨84、53和2丨3均 顯現出高效率(< 20%感染率)。 ί乍用 4星期齡的羅特歌諾(R()ter Gn_)品種蕃#植株在喷霧 室内以配製成的測試化合物(〇·〇2%活性成分)處理。施加 二天之後,蕃茄植株藉由喷霧孢子懸浮液(1χ1〇5分生孢子/ 毫升)至測試植株上進行接種。纟抓及95%相對濕度下 4天的培育期後,在成長室中評估罹病度。 化口物1.3 1.4、i.6〇a、i_6la和184均顯現出高效 率(< 50%罹病度)。 實施例 丄乍用
4生期齡的羅特歌諾品種蕃茄植株在喷霧室内以配製 成的測試化合物(0.02%活性成分)處理。施加二天之後: 蕃蘇植株藉由冑霧孢子懸浮液0,1〇5分生孢子/毫物測試 植株上進行接種。纟2GtA 95%相對濕度下3天的培育 期後,在成長室中評估罹病度。 化。物1.3、1.4、16〇a和} 61a在此測試中 良好的活性(<2G%罹病度)。 ^見出 ^ 200526672 且抗殼針孢蓋/小
J_ ,2星期齡的雷本(Riband)品種小麥植株在噴霧室内以配 製成的測試化合物(〇〇2%活性成分)處理。施加—天之後, 小麥植株藉由噴霧孢子懸浮液(lx 105》生孢子./毫升)至^試 植株上進行接種。纟23U 95%相對濕度下丨天的培: 期後,將植株留存在23。〇及6〇%相對濕度的溫室中b / 接種1 8天後評估罹病度。 :合物U、1·4、1.6…在此測試中均顯現出 良好的活性(<20%罹病度)。 粉病菌 / 葡 用 、5星期齡的古天典(Gutedel)品種葡萄幼苗在喷霧室内 以配製成的測試化合物(〇〇2%活性成分)處理。施加一天 萄植株藉由將感染㈣白粉病的植株在測試植株 方搖動進行接種。在26t& 6G%相對濕度下7立 育期後,在14m小時(光/暗)的光照處理下評估羅病度。口 …匕t::/.3、“、⑽和Wa在此測試中均顯現出 PL妤的浓性(<2〇%罹病度)。 4星期齡的麥金塔品種蘋果幼苗在嘴霧室内以配製成 的測試化合物(0.02%活性成分)處理。施加一天 果植株藉由藉㈣霧孢子懸浮液(4xlQ5分生 至、 測試植株上進行接種…rc一目對濕度下4天: 81 200526672 培育期後,將植株留存在2 PC及60%相對濕度的溫室中 天。再於2 1 °C及95%相對濕度下4天後評估罹病度。 化合物1.3、1.4、1.60a和在此測試中均顯現古 效率(<20%感染率)。 阿 2施例~H · _降抗隱匿柄鐘菌/小春(小^ 在施加配製物之前的兩天,i星期齡的阿玲娜品種小 麥植株藉由喷霧孢子懸浮液(1x1 05夏孢子/毫升)至測試植株 上進行接種。在2(TC及95%相對濕度下培育i天,及在2〇 °C及60%相對濕度的溫室!天後,經接種植株在喷霧室内 以配;|L成的測试化合物處理。在溫室中於2 〇。〇 /18。匚(曰/夜) 及60%相對濕度的額外8天培育期後評估罹病度。 2 1.3 均 化合物 1.3' 1.4、1.60a、1.6la、184、5 3 和 顯現出高效率(< 20%感染率)。 【圖式簡單說明】 Μ 【主要元件符號說明】 無 82
Claims (1)
- .200526672 十、申請專利範圍: 1. 一種式(I)化合物, ΧΛ etw Ν (R 其中X為Ο或S ; RING為苯基或 一至三個雜原子係個別獨立地選自氧、氮和硫的5_或6_員 雜環,該環經一至四個R4基取代;Ri為氫,選擇性經取 代之(C〗_4)烧基,甲醯基,選擇性經取代之(ci 4)烷基c(=〇), 遥擇性經取代之(U烧基c(=o)〇,選擇性經取代之(c ) 烧氧基(c^4)烧基,選擇性經取代之烯丙基,選擇性經取代 之炔丙基或選擇性經取代之丙二烯基;每個R2獨立地為鹵 素遥擇性經取代之(Cl·4)烧基,選擇性經取代之(C〗4)烧 氧基或選擇性經取代之(Cl.4)烷氧基(Ci4)烷基;^ ^ (CRaRb)m-Cy-(CRcRd)n-Y ;每個R4獨立地選自鹵素,c】3 烷基,Cw鹵烷基,c〗·3烷氧基(Ci j烧基和氰基;Ra,Rb'·3 和Rd分別冑立地為氫或選擇性經取代之(c“)烧基:G 為選擇性經取代之碳環狀或雜魏3·7員環且可為飽和、 不飽和或芳香性並選擇性地含有矽原子做為環員 和(CReRd)n可與Cy内之相同的碳或石夕原子鍵結,或經^ 2或3員環分離的不同原子鍵结;γ或 必好 為 Sl(0〆)(〇qz2)(〇sz), 唯其限制為當Cy含有矽原子Ag & ?于為%貝時則Υ亦可為氫;Ζ 83 200526672 為c】_4烷基或烯基(每個均可選擇性地經一個選自〇、 s和N的雜原子插入並可選擇性地經一至三個獨立選自齒 素之原子取代” Z1及z”蜀立地為甲基或乙基;历和打個 別獨立地為〇,卜2或和s個別獨立地為〇或1; 及r為〇 ’ 1或2,或為它的N-氧化物;唯其限制為當仍 和η均為〇且RING和Cy均為苯基時γ並非為三 基甲矽烷基。 其中X 2·根據申請專利範圍第}項之式(1)化合物 為氧。3·根據申請專利範圍帛1或2項之式⑴化合物,其 中Het為D比嗤基,D比咯基,硫苯基,呋喃基,噻唑基異 噻。坐基,ϋ基,異嚼哇基,三唾基,I定基義基, ㈣基,噠嗪基,5,6-二氫W喃基或5,6_二氫从氧硫雜環 己二烯基(〇Xathiinyl),其個別地經一至三個Μ基取代且經 由碳原子與CpXhNOl1)基相連接。。 二 】4.根據申請專利範圍帛i < 2項之式⑴化合物,其 中R1為氫,炔丙基’丙二烯基,f醯基,CH3C(=〇),C2H^卜⑺ 或 ch3och2c(=o) 〇 5·根據申請專利範圍帛i或2項之式⑴化合物,其 中R2係獨立地選㈣素,甲基,三㈣基和三氟甲氧基。 6.根據申請專利範圍第1或2項之式⑴化合物,其 令(CRR)m-Cy-(CRcRd)n-Y 在與攜有 N(Rl)c(=x)Het 基的 碳為鄰位處與『ring』 7·根據申請專利範 上的碳相鍵結。 圍第1或2項之式(I )化合物,其 84 200526672 中r為0或1。 8·—種式(Π )化合物, A W (丨丨)r3 其中RING,r,R2和R3如申請專利範圍第1項之定 義;A為NH2,NHCH(O),選擇性經取代的(I 4)烷基 C( = 〇)NH,選擇性經取代的(Cl_4)烷基 〇c(===〇)NH,Br,j, N〇2,〇S〇2CF3或N=C(C6H5)2 ;及R3在與A為對位處與碳 原子相鍵結。 9·一種使用於控制微生物及避免植物受其攻擊與感染 之組成物,其中該活性成分為根據申請專利範圍第〗項之 式(I )化合物及適當之載體。 1 0. —種控制或預防栽培植物受植物病原性微生物感染 之方法,其係將根據申請專利範圍第丨項之式(ι)化合物 或根據中請專利範圍第9項之組成物施加至植物、其部位 或其所在地。 十一、圖式: 益 85 200526672 七、 指定代表圖: (一) 本案指定代表圖為:第(無)圖。 (二) 本代表圖之元件符號簡單說明: 無 八、 本案若有化學式時,請揭示最能顯示發明特徵的化學式:6
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IL173470A0 (en) | 2006-06-11 |
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RU2006112856A (ru) | 2007-11-10 |
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AU2004274153A1 (en) | 2005-03-31 |
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AR045669A1 (es) | 2005-11-02 |
BRPI0414542A (pt) | 2006-11-07 |
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CO5700831A2 (es) | 2006-11-30 |
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