TW201014819A - Novle herbicides - Google Patents
Novle herbicides Download PDFInfo
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- TW201014819A TW201014819A TW98122383A TW98122383A TW201014819A TW 201014819 A TW201014819 A TW 201014819A TW 98122383 A TW98122383 A TW 98122383A TW 98122383 A TW98122383 A TW 98122383A TW 201014819 A TW201014819 A TW 201014819A
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- alkyl
- compound
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- 239000004009 herbicide Substances 0.000 title abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 730
- 125000000217 alkyl group Chemical group 0.000 claims description 227
- 238000000034 method Methods 0.000 claims description 164
- -1 n-diyl Chemical group 0.000 claims description 135
- 229910052739 hydrogen Inorganic materials 0.000 claims description 109
- 239000001257 hydrogen Substances 0.000 claims description 108
- 125000003545 alkoxy group Chemical group 0.000 claims description 101
- 229910052736 halogen Inorganic materials 0.000 claims description 97
- 150000002367 halogens Chemical class 0.000 claims description 95
- 125000001188 haloalkyl group Chemical group 0.000 claims description 89
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 82
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 82
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 76
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
- 125000004414 alkyl thio group Chemical group 0.000 claims description 57
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 241000196324 Embryophyta Species 0.000 claims description 33
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 20
- 230000002363 herbicidal effect Effects 0.000 claims description 19
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000002671 adjuvant Substances 0.000 claims description 9
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000006612 decyloxy group Chemical group 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 241000209504 Poaceae Species 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
- 125000004969 haloethyl group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical class 0.000 claims description 3
- 125000001425 triazolyl group Chemical class 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 238000009333 weeding Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims 1
- 150000002545 isoxazoles Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000000276 sedentary effect Effects 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- 125000005555 sulfoximide group Chemical group 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 79
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 239000002585 base Substances 0.000 description 63
- 239000000243 solution Substances 0.000 description 51
- 239000002904 solvent Substances 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
- 239000004480 active ingredient Substances 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 31
- 239000007789 gas Substances 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 20
- 239000000654 additive Substances 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
- 125000003282 alkyl amino group Chemical group 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 238000007796 conventional method Methods 0.000 description 15
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 14
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 230000035784 germination Effects 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 229910052763 palladium Inorganic materials 0.000 description 11
- 239000007921 spray Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000005864 Sulphur Substances 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 235000021419 vinegar Nutrition 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000003643 water by type Substances 0.000 description 9
- 241001621841 Alopecurus myosuroides Species 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 244000058871 Echinochloa crus-galli Species 0.000 description 8
- 240000004296 Lolium perenne Species 0.000 description 8
- 235000011999 Panicum crusgalli Nutrition 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000052 vinegar Substances 0.000 description 8
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- ZXBMIRYQUFQQNX-UHFFFAOYSA-N (4-fluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C=C1 ZXBMIRYQUFQQNX-UHFFFAOYSA-N 0.000 description 6
- UQPKIBHPQJMLMI-UHFFFAOYSA-N (4-phenylphenyl)hydrazine Chemical compound C1=CC(NN)=CC=C1C1=CC=CC=C1 UQPKIBHPQJMLMI-UHFFFAOYSA-N 0.000 description 6
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
- 241000209140 Triticum Species 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
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- 244000038559 crop plants Species 0.000 description 6
- 125000004966 cyanoalkyl group Chemical group 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- FTQYIDWPRGDBFN-UHFFFAOYSA-N (2-methylsulfonylphenyl)hydrazine Chemical compound CS(=O)(=O)C1=CC=CC=C1NN FTQYIDWPRGDBFN-UHFFFAOYSA-N 0.000 description 5
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- JFILLLZWNHOVHV-UHFFFAOYSA-N (3-nitrophenyl)hydrazine Chemical compound NNC1=CC=CC([N+]([O-])=O)=C1 JFILLLZWNHOVHV-UHFFFAOYSA-N 0.000 description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 5
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
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- 229910052708 sodium Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- PENWGQNPFRRVQI-UHFFFAOYSA-N (2-fluorophenyl)hydrazine Chemical compound NNC1=CC=CC=C1F PENWGQNPFRRVQI-UHFFFAOYSA-N 0.000 description 4
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- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Description
201014819 六、發明說明: 【發明所屬之技術領域】 本發明關於新穎的除草活性環狀二嗣類及其衍生物, 彼等之製備方法,含有該等化合物的組合物及彼等在控制 雜草,尤其在有用植物的作物中的雜草,或抑制植物生長 中的用途。 【先前技術】 具有除草作用的環狀二輞化合物被敘述在例如w〇 01/74770 以及 WO96/03366 中。 頃發現具有除草性及生長抑制性質的新穎環戊二酮化 合物以及其衍生物。 【發明内容】 本發明因此係關於式⑴化合物
其中 R1係為氫,甲基,乙基,正丙基,異丙基,鹵甲基, 鹵乙基,鹵素’乙烯基,乙炔基,甲氧基,乙氧基,鹵甲 氧基’函乙氧基,環丙基或齒環丙基, 201014819 ^ r2及r3獨立地為氫、齒素、(^-(:6烷基、Ci-Ce函烷基、 CVC6烷氧基、Cl_c6鹵烷氧基、c2-c6烯基、c2-c6鹵烯基、 C2-C6快基、C2-C6齒快基、C3-C6稀氧基、C3_C6由稀氧基 c3-c6炔氧基、。3_。6環烷基、Cl_c6烷硫基、Cl_c6烷基亞 磺醯基、C^-Ce烷基磺醯基、Ci-Ce烷氧基磺醯基、Ci-C6鹵 烷氧基磺醯基、氰基、硝基、苯基、經Cl-C4烷基、CrC3 鹵烷基、CVC3烷氧基、CVC3鹵烷氧基、氰基、硝基、函 素、CrC〗烷硫基、C/C3烷基亞磺醯基或C^-Cs烷基磺醯基 0 取代的苯基,或雜芳基或經CVCU烷基、CVC3鹵烷基、Ci_C3 烷氧基、鹵烷氧基、氰基、硝基、鹵素、CrG烷硫 基、CrCs烷基亞磺醯基或Ci-Cs烷基磺醯基取代的雜芳基’ R4為氫、cvc6烷基、CVC6鹵烷基、CVC6烷氧基 鹵烷氧基、c2-c6烯基、c2-c6鹵烯基、c2-c6炔基、c3-c6 烯氧基、c3-c6鹵烯氧基、c3-c6炔氧基、c3-c6環烷基、CVC6 烷硫基、CrCe烷基亞磺醯基、Ci-Ce烷基磺醯基、Ci-C:6烷 氧基磺醯基、鹵烷氧基磺醯基或氰基, ❹ R5、R6、R7、R8及R9獨立地為氫、函素、Ci-C6烷基、
Ci-C6鹵烷基、CrCe烷氧基、CVC6鹵烷氧基、C2-C6烯基、 C 2 · C 6 _稀基、C 2 _ C6快基、C3 - C 6婦氧基、C 3 _ C 6 _稀氧基、 C3-C6炔氧基、C3-C6環烷基、CVC6烷硫基、CVC6烷基亞 磺醯基、Ci-Ce烷基磺醯基、CfCe鹵烷基磺醯基、Ci-Ce烷 氧基續醯基、C^-Ce鹵炫氧基績醯基、氰基、琐基、苯基、 經Ci-CU烷基、(VC3鹵烷基、CVC3烷氧基、c〗-c3鹵烷氧 基、氰基、石肖基、鹵素、C!-C3烧硫基、C1-C3烧基亞確酿 5 201014819 基或c,-c3烧基確醯基取代的苯基,或雜芳基或經烧 基、Cl_C3齒燒基、㈣烧氧基、C”c3函烧氣基、氣基、 确基、幽素、CVCA硫基、Ci_Cj基亞續酿基、Ci_Cj 基磧酿基取代的雜芳基,或苯甲基或經Ci C4烧基、Ci C3 函烷基、CVC3烷氧基、Ci_C3函燒氧基、氰基、确基、齒 素、CVC3烧硫基、Cl_c3燒基亞續酿基或Ci_c3烧基續酿基 取代的苯甲基,或C3-C6環烧基Ci_C3燒基,其中環或鍵亞 甲基團視需要被氧原子或硫原子置換或 ❹ R與R或R與R —起與其所連接的碳原子形成視 需要取代的…員環’其視需要包含氧原子、硫原子或 氮原子,或 R5與R6 —起形成鍵, ❹ Q為包含至少-個選自雜原子的飽和 或單不飽和雜環基,纟未經取代或經為殘基的式=〇、=n_r10 或cvc4烧基、Cl-c4南燒基、Ci_C4燒氧基Ci_c2院基、c3_c6 環燒基苯基、、經燒基、Ci_c3由烧基、Ci_c氧基、 CVC3由烷氧基、氰基、硝基、函素、Ci_C3垸硫基、Ci_C3 烷基亞磺醯基或C,-C3烷基磺醯基取代的苯基,其中Rl0為 cvc6 烧基、Cl_c6 _ 貌基、C3_CyX院基、Ci_Cj氧基、 CrC6鹵烷氧基、Cl_C6烷基亞磺醯基、烷基磺醯基、 CVC6齒烧基幾基、Cl_C6燒氧基羰基、烷基胺基羰基、 CVCs 一烧基胺基幾基、Ci_c6鹵烷基亞磺醯基或Ci_c6鹵烷 基續醯基, m為1、2或3, 6 201014819 二 其中當m為2或3時,R6或R7可具有不同意義,及 G為氫或農業上可接受之金屬、銕、銨、或潛伏化基團 (latentiating group) 〇 【實施方式】
式I化合物的取代基定義中,各烷基部分—單獨抑或是 作為較大型基團(例如烷氧基、烷硫基、烷基羰基、烷基 胺基羰基及二烷基胺基羰基)的一部分係為直鏈或支鏈且 為,舉例來說,甲基、乙基、正丙基、正丁基、正戊基、 正己基、異丙基、正丁基、二級丁基、異丁基、三級丁基 或新戊基。烷基基團係適宜為〇1至C6烷基基團,但較佳為 CrC4烷基基困,更佳為Ci_Cz烷基基團。烯基與炔基部分 可為直鏈或支鏈形式,而烯基部分一適當的話一可呈(E) -或(Z) 構形。例子有乙烯基、烯丙基與块丙基。稀基與 炔基邛刀可含有呈任何組合之一或多個雙鍵及/或參鍵。可 理解到的是丙二稀基與炔基縣純括錢㈣詞内。 鹵素為氣、氣、溴或硬。
函烷基是被-或多個相同或不同的_素原子取代的 基且為,舉例來說,CF3、CF2C1、CF2H、CC12HFCH
⑽2、BrCH2、CH3CHF、(CH3)2CF,CF3CH2^HF2CH 雜方基语較佳意指包含至少一個雜原子且由單 環組成。較佳者’單環將包含多至三個 個將較佳選自氮、“及硫的雜環 子。該類基團的例子包括…基、嗟吩 7 201014819 唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、異噁 唑基、噻唑基、異噻唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、 1,2,5-噁二唑基、丨,2,3·噻二唑基、1,2,4-噻二唑基、1,3,4· 嗔二唾基、1,2,5-嗟二》坐基、咐*咬基、嘴咬基、"荅嗓基 '。比 嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、苯幷呋 _基、笨幷異β夫味基、苯幷嗟吩基、苯幷異嘆吩基、t^|n朵 基、異吲哚基、吲唑基、笨幷噻唑基、笨幷異噻唑基、苯 幷噁唑基、苯幷異噁唑基、苯幷咪唑基、2,1,3-苯幷噁二唑、 喹琳基、異啥琳基、嗜淋基、吹嗓基、喧唾蛛基、啥喔琳 基、萘咬基、苯幷三唤基、嘌吟基、嗓咬基以及朵嗓基。 雜芳香基的較佳例子係包括吡啶基、嘧啶基、三嗪基、 噻吩基、呋喃基、噁唑基、異噁唑基、213_苯幷噁二唑及 嘆β坐基。 較佳雜芳香基的另外基團包括呋喃基、噻吩基吼唑 基、1,2,3-三唑基、1,2,4-三唑基、吡啶基、嘧啶基、嗒嗪基、 他嗪基、喹啉基、異喹啉基、口辛啉基(cinn〇linyl)、喹唑 淋基或啥喔嚇·基。 雜環基用詞較佳指的是合右s^ ^ J3有至多8個原子的非芳香 族、較佳單環或雙環系統,其句括5 ,丨、加,^ a 丹巴栝至少一個(較佳為一或 二個)選自於0、S與N的雜屌;分此β _ J雠原子。該類環的實例包括13_ 二噻烷、1,3-二噁炫;' 1,4-二喔燒、 四氫吡喃、六氫吡啶、嗟炫^ ’ (l,3-dioxolane)、四氫呋喃、四氫嗟吩 嗎琳、硫代嗎琳、β辰嗪、 三亞甲亞胺(azetidine)、 1,3- —氧雜戊環 0比略咬、味唾琳、 氧雜環丁烷(oxetane) 環硫烷 201014819 (thietane)、吖丙烧(aziridine)、環氧化物及噻喃(thiirane)。 較佳的雜環基圓實例包括1,3 -二鳴烧、嗎嚇、硫代嗎 啉、四氫吡喃、1,3-二氧雜戊環、四氫呋喃及四氫噻吩。 環烷基較佳包括環丙基,環丁基,環戊基和環己基。 對經取代的雜環基團例如分別由R6與R7,以及R8與 R9所形成的環而言,較佳為一或多個取代基係獨立地選自 鹵素、烧基、鹵炫基、Ci-C^烧氧基、C^-Ce鹵 烧氧基、CVC:6烷硫基、CVC6烷基亞磺醯基、CVC6烷基磺
醯基、氰基或硝基。欲被理解的是二烷基胺基取代基係包 括該等其中二烷基基團和其所連接的N原子共同形成五、 六或七員雜環’該雜環可含有一或二個選自於〇、N或s 的其他雜原子並可視需要的地被一或二個獨立選定的(Ci 6) 烧基基團所取代《當雜環係藉由使N原子上的兩基團聯接 而形成時,則所生成的環係適宜為吡咯啶、六氫吡啶以及 硫代嗎啉及嗎啉,其各別可被一或二個獨立選定的(Ci 烷 基基團取代。 本發明亦關於該等式I化合物能夠與胺,鹼金屬以及鹼 土金屬驗或四級銨鹼形成的鹽類。 在作為鹽形成者的鹼金屬及鹼土金屬氫氧化物當中, 應該特別要提到的是氫氧化鋰,氫氧化鈉,氫氧化鉀,氫 虱化鎂,以及氫氧化鈣,但是特別的是氫氧化鈉以及氫氧 化鉀。本發明的式!化合物亦包括水合物’其係 間所形成者。 取朋 適合於銨鹽形成的胺的實例包括氨與一級、二級及 9 201014819 級烷基胺、Ci-C^羥基烷基胺以及c2-c4烷氧基烷基 胺,例如甲胺、乙胺、正-丙胺、異丙胺、四種丁胺異構物、 正-戊胺、異戊胺、己胺、庚胺、辛胺、壬胺、癸胺、十五 烷胺、十六烷胺、十七烷胺、十八烷胺、甲基乙胺、甲基 異丙胺、甲基己胺、甲基壬胺、甲基十五烷胺'曱基十八 烷胺、乙基丁胺、乙基庚胺、乙基辛胺、己基庚胺、己基 辛胺、二甲胺、二乙胺、二-正-丙胺、二異丙胺、二·正-丁 胺、二-正-戊胺、二異戊胺、二己胺、二庚胺、二辛胺、乙 醇胺、正-丙醇胺、異丙醇胺、N,N-二乙醇胺、N-乙基丙醇 胺、N-丁基乙醇胺、稀丙胺、正-丁-2-婦胺、正-戊-2-稀胺、 2,3-二曱基丁-2-烯胺、二丁-2-烯胺、正-己-2-烯胺、丙稀二 胺、三甲胺、三乙胺、三-正-丙胺、三異丙胺、三·正_ 丁胺、 三異丁胺、三-二級丁胺、三-正-戊胺、甲氧基乙胺及乙氧 基乙胺;雜環胺,例如Π比咬、啥啭、異啥琳、嗎琳、六氫 «比啶、吡咯啶、吲哚啉、琨啶及氮雜卓;一級芳胺,例如 苯胺、曱氧基苯胺、乙氧基苯胺、鄰-、間-和對-曱苯胺、 伸苯二胺、聯苯胺、萘胺及鄰-、間-和對-氣苯胺,但是尤 其為三乙胺、異丙胺及二異丙胺。 適合於鹽形成的較佳的四級銨鹼對應於例如式 [N(RaRbRcRd)]〇H,其中 Ra、Rb、Rc 及 Rd 彼此獨立為 Cl_c4 烧基。更多具有其他陰離子的適合的四烷基銨鹼可藉由例 如陰離子交換反應而獲得。 農業上可接受之金屬為鹼金屬或鹼土金屬離子,例如 納、鉀、鎂及鈣離子,以及過渡金屬離子’例如鋼及鐵離 201014819 子。合適的絲子為NH4+,烧基錢,二坑基錄,三烧基錄 以及四烧基錢離子。合適的锍離子為三烧基疏離子,例如 三甲基疏離子。 理應了解的是,那些式1化合物(其巾G為如以上所述 的金屬銨或錡且如此代表陽離子,相對應的負電荷大部 分於橫越〇-c=c-c=o單元離域化。 k些潛伏化基團G的選擇允許其在施予處理之區域或 植物之前、期間或之後以生化、化學或物理法中的一種或 © 、組合移除,以供給其中(^H之式J化合物。這些方法的 實例包括料裂解法、化學水解法及光分解法帶該等 潛伏化基團G的化合物可提供某些優點,例如被處理之植 物經改進之角質層穿透;增加之作物耐受性;在含有其他 除草劑、除草劑安全劑(safener)、植物生長調節劑、殺真菌 劑或殺尾蟲劑之調配混合物中經改進之相容性或穩定性; 或減少在土壤中被濾掉。 潛伏化基團G較佳地選自Ci_Cs烷基、C2_C8鹵烷基、 © 苯基q-C8烷基(其中苯基可視需要被Ci_C3烷基、Ci_C3 齒烧基、CVC3炫氧基、CVC:3鹵烷氧基、CVC3烷硫基、CVC3 烷基亞磺醯基烷基磺醯基、鹵素、氰基或硝基取代)、 雜芳基C]-C8烷基(其中雜芳基可視需要被Ci_c3烷基、 CVC3鹵烷基、(VC3烷氧基、Ci_c3鹵烷氧基、c丨_c3烷硫 基、CrC3烷基亞磺醯基、Cl_c3烷基磺醯基、鹵素、氰基 或硝基取代)、C3-C8烯基、c3_c8鹵烯基、C3_C8炔基、 C(Xa)-Ra - C(Xb)-Xc-Rb Λ C(Xd)-N(Rc)-Rd ^ -S02-Re > 11 201014819 -p(xe)(Rf)-Rg 或 cH2-xf-Rh,其中 xa、xb、xc、xd、x 及 xf彼此獨立為氧或硫;
Ra 為 H、C!-Ci8 院基、C2-C18 稀基、C2-C18 炔基、Ci-Ci〇 鹵烷基、〇ν(:10氰基烷基、Ci-Ci〇硝基烧基、炫基、 C^-Cs烷基胺基C「C5燒基'二(C2-C8烧基)胺基CrCs炫基、 C3-C7環烷基Ci-Cs烷基、CkCs烷氧基CrCs烧基、c3-c5 烯氧基Ci-Cs烷基、C3-C5炔基CVC5氧基烧基、CVC5炫硫 基Ci-Cs烷基、C1-C5烷基亞磺醯基Ci-Cs烷基、CVC5炫基 磺醯基Ci-Cs烷基、C2-C8亞烷基胺基氧基Ci-Cs烷基、C1-C5 烷基羰基CrCs烷基、CfCs烷氧基羰基CrCs烷基、胺基 幾·基C 1 - C 5烧基、C 1 - c 5燒基胺基幾基C 1 - C 5烧基、C 2 - C 8 — 烷基胺基羰基Ci-Cs烷基、CrCs烷基羰基胺基CrCs烷基、 N-Ci-Cs烷基羰基-N-Ci-C5烷基胺基(:丨-(:5烷基、C3-C6三烷 基甲矽烷基CrCs烷基、苯基Ci-Cs烷基(其中苯基可視需 要被CVC3烷基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷 氧基、Ci-Cs烷硫基、Crq烷基亞磺醯基、Ci-C^烷基磺醯 基、鹵素、氰基或硝基取代)、雜芳基(^-(:5烷基(其中雜 芳基可視需要被C1-C3烷基、(^-(:3鹵烷基、CrCs烷氧基、 CVC3鹵烷氧基、CVC3烷硫基、Ci-Cs烷基亞磺醯基、CVC3 烷基磺醯基、鹵素、氰基或硝基取代)、C2-C5鹵烯基' c3-c8 環烷基、苯基或被CrC3烷基、C^-Cs鹵烷基、Ci_C3烷氧基、 G-C3鹵烷氧基、鹵素、氰基或硝基取代之苯基、雜芳基或 被(VC3烧基、CVC3 _院基、CVC3烧氧基、CVC3自烷氧 基、齒素、氰基或硝基取代之雜芳基; 201014819 : Rb 為 C^-Cu 烧基、C3-C18 烯基、C3-C18 炔基、c2-c10 鹵烷基、(VCio氰基烷基、CVCw硝基烷基、C2_C10胺基烧 基、CVC5烷基胺基CVC5烷基、c2-c8二烷基胺基CVC5烷 基、C3-C7環烷基CVC5烷基、Ci-C5烷氧基c「c5烷基、c3-c5 烯氧基CVC5烷基、C3-C5炔氧基CVC5烷基、c「c5烷硫基 CVC5烷基、CrCs烷基亞磺醯基CrCs烷基、CVC5烷基磺 醯基CVC5烷基、C2-C8亞烷基胺基氧基CVC5烷基、CVC5 烷基羰基CrCs烷基、CrCs烷氧基羰基CrCs烷基、胺基 @ 羰基Ci-C5烷基、CVCs烷基胺基羰基CVC5烷基、c2-c8二 烷基胺基羰基Ci-Cs烷基、Ci-Cs烷基羰基胺基CrCs烷基、 N-CrCs烷基羰基-N-C丨-C5烷基胺基CrCs烷基、C3-C6三烷 基矽烷基CrCs烷基、苯基Ci-Cs烷基(其中苯基可視需要 被CVC3烷基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧 基、CVC3烷硫基、CVC3烷基亞磺醯基、CVC3烷基磺醯基、 鹵素、氰基或硝基取代)、雜芳基C^-Cs烷基(其中雜芳基 可視需要被CVC3烷基、CVC3鹵烷基、cvc3烷氧基、CVC3 Ο 鹵烷氧基、烷硫基、c^-Cs烷基亞磺醯基、(vq烷基 磺醯基、鹵素、氰基或硝基取代)、c3-c5鹵烯基、c3_c8 環烷基、苯基或被Ci-C:3烷基、c^-Cs鹵烷基、Ci-Cs烷氧基、 Cj-C3鹵烷氧基、鹵素、氰基或硝基取代之苯基、雜芳基或 被Crq烷基、CVC3鹵烷基、Cl-C3烷氧基、Cl-c3鹵烷氧 基、由素、氰基或硝基取代之雜芳基, 1^及Rd彼此獨立為氫、Cl-Cl。烷基、C3_Cl。烯基、C3_Ci〇 炔基、C2-C10鹵烷基' eve”氰基烷基、cVCw硝基烷基、 13 201014819
Ci-Ci〇胺基烧基、C1-C5烧基胺基Ci-Cs烧基、C2-C8二烧基 胺基C1-C5烧基、C3-C7環烧基Ci-C5烧基、Ci-C5烧氧基 Ci-C5烧基、C3-C5稀氧基CrCs烧基、C3-C5炔氧基Ci-Cs 烧基、CrCs烧硫基Ci-C5烧基、Ci-Cs烧基亞確醢基Ci-C5 烧基、C1-C5炫•基確酿基C1-C5烧基、C^-C8亞烧基胺基氧基 Ci-C5烧基、Ci-C〗烧基幾基C1-C5烧基、C^-Cs烧氧基幾基 Ci-C5统基、胺基幾基C1-C5炫基、C^-Cs烧基胺基獄基C1-C5 统基、C2-C8二烷基胺羰基Ci-C5烷基' Ci-C5烷基羰基胺基 C1-C5烧基、N-C1-C5燒基幾·基-N-C2-C5院基胺基烧基、C3-C6 三烷基矽烷基CrCs烷基、苯基CrCs烷基(其中苯基可視 需要被CVC3烷基、CVC3卤烷基、(VC3烷氧基、CVC3鹵 烷氧基、Ci-q烷硫基、CrCs烷基亞磺醯基、Ci-Cs烷基磺 醯基、鹵素、氰基或硝基取代)、雜芳基CkCs烷基(其中 雜芳基可視需要被Ci-Cs烷基、(^-(:3鹵烷基、CrCs烷氧基、 CU-C3鹵烷氧基、CrCs烷硫基、(VC3烷基亞磺醯基、CJ-C3 烷基磺醯基、鹵素、氰基或硝基取代)、c2-c5鹵烯基、c3-c8 環烷基、苯基或被(^-(:3烷基、Ci-Cs鹵烷基烷氧基、 Ci-C:3鹵烷氧基、鹵素、氰基或硝基取代之苯基、雜芳基或 被CrCs烷基、CVC3鹵烷基、CVC3烷氧基、(VC3鹵烷氧 基、鹵素、氰基或硝基取代之雜芳基、雜芳基胺基或被d-Cs 烧基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧基、鹵素、 氣基或墙基取代之雜芳基胺基、二雜芳基胺基或被Cl-C3 烷基、CVC3鹵烷基、CVC3烷氧基、鹵烷氧基、鹵素、 II基或碗基取代之二雜芳基胺基、苯胺基或被Cl-C3烷基、 201014819 : CVC3鹵烷基、CVC3烷氧基、Ci-q鹵烷氧基、鹵素、氰基 或硝基取代之苯胺基、二苯胺基或被Ci-Cs烷基、鹵 烷基、Ci-C^烷氧基、(^-(:3鹵烷氧基、鹵素、氰基或硝基 取代之二苯胺基、或C3-C7環院基胺基、二- C3-C7環烧基胺 基或〇3-(:7環烷氧基,或1^與Rd可連結在一起形成3-7員 環,視需要包括一個選自〇或s之雜原子;
Re 為 Ci-Ci〇 烧基、C2_Ci〇 稀基、C2-C10 快基、Ci_Ci〇 鹵烷基、Ci-Cw氰基烷基、G-Cw硝基烷基、Ci-Cw胺基烷 g 基、CrCs烷基胺基Ci-Cs烷基、C2-C8二烷基胺基C^-Cs 烧基、C3-C7環烧基C1-C5烧基、C1-C5烧氧基Ci-C5烧基、 C3-C5稀氧基C1-C5烧基、C3-C5快氧基C1-C5烧基、C1-C5 烧硫基C1-C5烧基、C1-C5烧基亞績酿基C1-C5烧基、C1-C5 烧基績酿基C1-C5烧基、C2-C8亞烧基胺氧基C1-C5烧基、 CVC5烷羰基CVC5烷基、CVC5烷氧基羰基CrCs烷基、胺 基羰基CrCs烷基、CVC5烷基胺基羰基CVC5烷基、c2-c8 二烷基胺基羰基Ci-Cs烷基、CrCs烷基羰基胺基CrCs烷 φ 基、N-CVC5烷基羰基-N-CrCs烷基胺基CVC5烷基、C3-C6 三烷基矽烷基烷基、苯基CrCs烷基(其中苯基可視 需要被C1-C3院基、C1-C3鹵烧基、C1-C3烧氧基、C1-C3鹵 烷氧基、CrCs烷硫基、CrC3烷基亞磺醯基、CrCs烷基磺 醯基、鹵素、氰基或硝基取代)、雜芳基C^-Cs烷基(其中 雜芳基可視需要被CrG烷基、Ci-Cs鹵烷基、(^-(:3烷氧基、 Ci-C3 _烧氧基、C1-C3烧硫基、C1-C3烧基亞罐酿基、C1-C3 烷基磺醯基、鹵素、氰基或硝基取代)、c2-c5鹵烯基、c3-c8 15 201014819 . 環烷基、苯基或被CrCs烷基、CrCs鹵烷基'CrCs烷氧基、 Q-C3鹵烷氧基、鹵素、氰基或硝基取代之苯基、雜芳基或 被CVC3烷基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧 基、鹵素、氰基或硝基取代之雜芳基、雜芳基胺基或被Ci-C^ 烧基、C 1 - C3 _院基、C 1 - C3烧氧基、.C 1 - C3 ί炫》氧基、齒素、 氰基或硝基取代之雜芳基胺基、二雜芳基胺基或被Ci-Cj 烷基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧基、鹵素、 氰基或硝基取代之二雜芳基胺基、苯胺基或被CrCs烷基、 CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧基、鹵素、氰基 或硝基取代之苯胺基、二苯胺基或被(^-(^3烷基、CrC3鹵 烷基、烷氧基' 鹵烷氧基、鹵素、氰基或硝基 取代之二苯胺基;或c3-c7環烷基胺基、二(c3-c7環烷基) 胺基或C3-C7環烧氧基、Cl_Cl〇烧氧基、Cl-ClQ_烧氧基、 Ct-Cs烷基胺基或C2-C8二烷基胺基, R/及Rg彼此獨立為CVCm烷基、C2-C1()烯基、C2-C10 炔基、C1-C10烧氧基、C1-C10鹵烧基、C1-C10氰基烧基、C1-C10 石肖基烧基、Ci-CiG胺基烧基、C1-C5烧基胺基Ci_C5院基、 C2-Cs二烧基胺基C1-C5烧基、C3-C7環烧基C1-C5烧基、C1-C5 烧氧基C1-C5烧基、C3-C5稀氧基C1-C5烧基、C3-C5炔氧基 CVC5烷基、CrCs烷硫基CVC5烷基、CVC5烷基亞磺醯基 C1-C5炫基、Ci-C5烧基確醯基C1-C5烧基、C2-C8亞院基胺 氧基C1-C5炫基、C1-C5烧幾·基C1-C5烧基、Ci-C5烧氧基幾· 基Ci-C5烷基、胺基羰基C1-C5烷基、CrC:5烷基胺基羰基 C 1 - C 5烧基、C 2 - C 8二烧基胺幾基C 1 - C 5烧基、C 1 - C 5烧無·基 201014819 胺基CVC5烷基、N-CVC5烷基羰基-N-C2-C5烷基胺基烷基、 C3-C6三烷基矽烧基(VCs烧基、苯基CVC5炫基(其中苯 基可視需要被CVC3烷基、Ci-C^鹵烷基、Ci-Cs烷氧基、CVC3 鹵烷氧基、Ci-C:3烷硫基、CrCs烷基亞磺醯基、c!-c3烷基 磺醯基、鹵素、氰基或硝基取代)、雜芳基Ci-Cs烷基(其 中雜芳基可視需要被C1-C3烧基、C1-C3鹵烧基、C1-C3烧氧 基、CVC3鹵烷氧基、(VC3烷硫基、(^-(:3烷基亞磺醯基、 Cl-c3烷基磺醯基、鹵素、氰基或硝基取代)、c2-c5鹵烯 Φ 基、c3-c8環烷基、苯基或被CVC3烷基、CVC3鹵烷基、CVC3 烷氧基、(^-(:3鹵烷氧基、鹵素、氰基或硝基取代之苯基、 雜芳基或被CVC3烷基、CVC3鹵烷基、CVC3烷氧基、(VC3 鹵烷氧基、i素、氰基或硝基取代之雜芳基、雜芳基胺基 或被Ci-Cs烷基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷 氧基、齒素、氰基或硝基取代之雜芳基胺基、二雜芳基胺 基或被cvc3烷基、Crq鹵烷基、烷氧基、CVC3鹵 烷氧基、i素、氰基或硝基取代之二雜芳基胺基、苯胺基 Ο 或被CVC3烷基、CVC3鹵烷基、CVC3烷氧基、(^-(:3鹵烷 氧基、鹵素、氰基或硝基取代之苯胺基、二苯胺基或被Ci-Cs 烧基、C1-C3鹵烧基、C1-C3烧氧基'Ci-Cs鹵烧氧基、鹵素、 氰基或硝基取代之二苯胺基、或c3-c7環烷基胺基、c3-c7 二環烧基胺基或C3-C7環烧氧基、Ci-Cto鹵烧氧基、C^-Cs 烷基胺基或c2-c5二烷基胺基、苯甲氧基或苯氧基,其中苯 甲基及苯基可依次被Ci-Cs烷基、(^-〇:3鹵烷基、C^-Cs烷氧 基、CrG鹵烷氧基、鹵素、氰基或硝基取代,及 17 201014819
Rh 為 Ci-Ci〇 烧基、C3-Ci〇 烯基、C3-Ci〇 炔基、Ci-Ci〇 鹵烧基、C1-C10氰基烧基、Ci-Ci〇碗基烧基、C2-Ci〇胺基炫> 基、CVC5烷基胺基CVC5烷基、C2-C8二烷基胺基CVC5烷 基、C 3 - C 7環炫•基C 1 - C 5烧基、C 1 - C 5烧氧基c 1 - C 5烧基、C 3 - c 5 稀氧基C1-C5烧基、C3-C5快氧基C1-C5烧基、C1-C5烧硫基 CVC5烷基、CVC5烷基亞磺醯基CrCs烷基、CVC5烷基磺 醯基CVC5烷基、C2-C8亞烷基胺基氧基CrCs烷基、Ci-Cs 烷基羰基CrCs烷基、CrCs烷氧基羰基CrCs烷基、胺基 羰基CVC5烷基、CVC5烷基胺基羰基CU-C5烷基、(:2-<:8二 ❹ 烷基胺羰基CrCs烷基、CrCf;烷基羰基胺基Ct-Cs烷基、 N-q-Cs烷基羰基-N-CpCs烷基胺基CVC5烷基、C3-C6三烷 基矽烷基C^-Cs烷基、苯基烷基(其中苯基可視需要 被CVC3烷基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧 基、CrCs烷硫基、Crq烷基亞磺醯基、CrCs烷基磺醯基、 鹵素、氰基或硝基取代)、雜芳基Ci-Cs烷基(其中雜芳基 可視需要被CVC3烷基、CVC3鹵烷基、CVC3烷氧基、CVC3 鹵烷氧基、CVC3烷硫基、CVC3烷基亞磺醯基、CVC3烷基 ◎ 磺醯基、鹵素、氰基或硝基取代)、苯氧基C^-Cs烷基(其 中苯基可視需要被CrCs烷基、Ci-C^鹵烷基、CrCs烷氧基、 CVC3鹵烷氧基、CJ-C3烷硫基、CVC3烷基亞磺醯基、CVC3 烧基磺酿基、鹵素、氰基或硝基取代)、雜芳氧基Ci_C5 烧基(其中雜芳基可視需要被Cl-C3烷基、(^-0:3鹵烷基、 CVC3烧氧基、(:,-(^3鹵烷氧基、Cl_c3烷硫基、c丨-c3烷基 亞續酿基、CrCs烷基磺醢基、鹵素、氰基或硝基取代)、 18 201014819 c3-c5齒烯基、c3_c8環烷基、苯基或被Ci_c3烷基、Ci_c3 鹵烷基C^c:3烷氧基、Ci-C^鹵烷氧基、鹵素或硝基取代 之苯基、或雜芳基或被C1-C3烷基、CVC3鹵烷基、(:「C3 烷氧基C^c:3鹵烷氧基、鹵素、氰基或硝基取代之雜芳基。 特别的疋,潛伏化基團G係為C(Xa)-Ra或c:(Xb)-Xc-Rb 且X R、xb、xc、以及Rb的意義係如以上所定義。 較佳者,G係為氫,鹼金屬或鹼土金屬,其中以氫為最 佳。
物形式存在。當G為氫時,則式(1)化合物可以不同的互變 異構物形式存在:
依據取代基的本性而定,式⑴化合物可以不同的異構
本發明涵蓋以所有比例的所有這些異構物與互變異構 式及異其構’ #取代基包括雙㈣1順式-及反 的範:: 這些異構物也在所請求之式⑴化合物 在式⑴化合物的較佳基團中D甲基、乙基或甲氧 較佳者,R2及R3獨立地為氫、_素、 鹵烷基、c2-c6烯基、c c炔基、 6、元基、Cl-Ce …基、—一、硝…4:= 19 201014819 取代之苯基,以及,更佳者,R2及R3獨立地為氫、氣、溴、 , 甲基、甲氧基、乙基、乙氧基、乙烯基、乙烯基、笨基或 經甲基、二氟甲基、氰基、硝基、氟、氣或甲基磺醯基取 代的苯基。 在式(I)化合物的另外較佳基團中,R2及R3獨立地為嗟 吩基、經(VC3烷基、鹵烷基、Ci-C3烷氧基、Ci_c3 鹵烧氧基、氰基、硝基、鹵素、Ci-C:3娱;硫基、烧基 亞確酿基或C1-C3烧基績酿基取代的售吩基,吱味基 '經 CrG烷基、Ci-Cs鹵烷基、CVC3烷氧基、CVC3鹵烷氧基、 g 氰基、硝基、鹵素、C^-C:3烷硫基、C^-Cs烷基亞磺醯基或 Ci-C3炫基續酿基取代的吱鳴基,。比〇坐基,經燒基、 CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧基、氰基、硝基、 鹵素、C^C:3烷硫基、CrC3烷基亞磺醯基或C!-C3烷基續醯 基取代的吡唑基,噻唑基,經Ci-C^烷基、(^-(:3鹵烷基、 C1-C3烷氧基、CVC3鹵烷氧基、氰基、硝基、鹵素、Ci-C^ 烷硫基、C^C:3烷基亞磺醯基或Crq烷基磺醯基取代的噻 唾基,噁唑基,經CVC3烷基、c〗-c3鹵烷基、c〗-c3烷氧基、 © Ci-C3鹵烷氧基、氰基、硝基、鹵素、c^-Cs烷硫基、CVC3 烧基亞確酿基或C1-C3烧基績酿基取代的《•惡β坐基,異°塞β生 基’經CVC3烷基、CVC3鹵烷基、(VC3烷氧基、CVC3鹵 燒氧基、氰基、硝基、鹵素、CVC3烷硫基、cvc3烷基亞 磺醯基或C!-C3烷基磺醯基取代的異噻唑基,異噁唑基,經 Crq烷基、CVC3鹵烷基、(VC3烷氧基、CVC3鹵烷氧基、 氡基、硝基、鹵素、烷硫基、Ci-Cs烷基亞磺醯基或 20 201014819 ' C^-Cs烷基磺醯基取代的異噁唑基,三唑基’經CrCs烷基、 CVC3鹵院基、CVC3烧氧基、CVC3鹵烧氧基、氰基、硝基、 鹵素、C!-C3烷硫基、Crq烷基亞磺醯基或CrCs烷基磺醯 基取代的三唑基,噁二唑基,經CrG烷基、Crq鹵烷基、 C1-C3烧氧基、C1-C3齒烧氧基、氰基、石肖基、由素、C1-C3 烧硫基、C1-C3烧基亞續酿基或C1-C3烧基續酿基取代的°惡 二唑基,噻二唑基,經(VC3烷基、CVC3鹵烷基、CVC3 烧氧基、C1-C3鹵烧氧基、氰基、瑞基、鹵素、C1-C3烧硫 φ 基、CrCs烷基亞磺醢基或Crq烷基磺醯基取代的噻二唑 基,四唑基,經(VC3烷基、CVC3鹵烷基、CVC3烷氧基、 C1-C3鹵烧氧基、氰基、頌基、卤素、C1-C3烧硫基、C1-C3 烷基亞磺醯基或Ci-Cs烷基磺醯基取代的四唑基,"比啶基, 經CVC3烷基、CVC3鹵烷基、κ3烷氧基、鹵烷氧 基、氰基、硝基、鹵素、CVC3烷硫基、c「c3烷基亞磺醯 基或烷基磺醯基取代的吡啶基,嘧啶基,經(^-(:3烷 基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧基、氰基、 Θ 硝基、鹵素、cvc3烷硫基、CVC3烷基亞磺醯基或c!-c3 烷基磺醯基取代的嘧啶基,嗒嗪基,經CrC3烷基、CrC:3 鹵烷基、CVC3烷氧基、(VC3鹵烷氧基、氰基、硝基、齒 素、CrCs烷硫基、Ci-C^烷基亞磺醯基或Ci-Cs烷基磺醯基 取代的嗒嗪基,吡嗪基,經Ci-Cs烷基、C^-Cs鹵烷基、CrC3 烷氧基、CVC3鹵烷氧基、氰基、硝基、鹵素、CVC3炕琉 基、Ci-q烷基亞磺醯基或Ci-Cs烷基磺醯基取代的°比°桊 基,三嗪基,經CVC3烷基、CVC3鹵烷基、CVC3烷氧基、 21 201014819
Ci-C3鹵燒氧基 '氰基、硝基、鹵素、CKC3貌硫基、 烷基亞磺醯基或Ci-C:3烷基磺醯基取代的三》秦基。 較佳者,R3為氫。 較佳者’R4為氫、曱基、乙基、正丙基、異丙基、邊 甲基、齒乙基、蟲素、乙烯基、乙炔基、甲氧基、乙氧基、 鹵曱氧基或鹵乙氧基,以及R4更佳為氫、甲基、乙基、氣、; 溴、乙烯基、乙炔基、曱氧基或乙氧基。 較佳者’ R1、R2以及R4、為曱基且R3為氫。
在式(I)化合物的另外較佳基團中,R5為氫、鹵素、Ci_C6 烷基、q-C5齒烷基、Cl_Ce烷氧基或Ci_C6齒烷氧基且更 佳者’ R5及為氫或甲基。 較佳者,在式⑴化合物中,R6以及R7獨立地為氫、函 素、Ci-c6烷基、Cl_c5 _燒基、Ci_c^氧基或Cl ^齒炫 氧基’且更佳者,R6以及R7獨立地為氫或甲基。。 在式⑴化合物的較佳基團中,r8以及r9獨立地為氮、 鹵素、CA燒基、Cl_c5 _燒基、Ci_Cd氧基或鹵 燒氧基,且更佳者’ R8以及r9獨立地為氫或甲基。
較佳的飽和或單不飽和環Q為下式者
Qe β (¾ 22 201014819
23 201014819
24 201014819
❹ 其中 R為氫、鹵素、CVC6烷基、CVC6鹵烷基、crC6炫氧 基、CVC6鹵烷氧基、c2-C6烯基、c2-c6鹵烯基、C2-C6快 基、c2-c6鹵炔基、c3-c6烯氧基、C3-C6鹵烯氧基、C3-C6 炔氧基、CVC6環烷基、〇^_(:6烷硫基、(^-(^烷基亞磺醯基、 Ci-Ce烷基磺醢基、(^-(:6烷氧基磺醯基、C^-Ce鹵烷氧基磺 醯基、氰基、硝基、苯基、經q-CU烷基、C1-C3鹵烷基、 φ Cl_C3烷氧基、CVC3鹵烷氧基、氰基、硝基、鹵素、Cl-C3 烷硫基、Ci-q烷基亞磺醯基或Ci-Cs烷基磺酿基取代的苯 基,或雜芳基或經烷基、鹵烷基、CrC3烷氧基、 Ci-C3鹵烷氧基、氰基、硝基、鹵素、CVC3烷硫基、CrG 烷基亞磺醯基或Ci-Cs烷基磺醯基取代的雜芳基, R’為氫、CVC6烷基、CVC6 i烷基、C3-C7環烷基、Ci-Ce 烷氧基、鹵烷氧基、CrCe烷基亞磺醯基、烷基 磺醯基、烷基羰基、C!-C6鹵烷基羰基、CrCe烷氧基 羰基、CrCe烷基胺基羰基、C2-C8二烷基胺基羰基、c6-c10 25 201014819 芳基磺醯基、c6-c10芳基羰基、c6-c1()芳基胺基羰基、c7-c16 芳基烷基胺基羰基、雜芳基磺醯基、雜芳基羰 基、雜芳基胺基羰基、(:2-(:15雜芳基烷基胺基羰基, R”為氫、CVC6烷基、CVC6鹵烷基、C3-C7環烷基、CVC6 烷氧基、CrCe鹵烷氧基' Ci-Ce烷基亞磺醯基、(^-(:6烷基 磺醯基、烷基羰基、C丨-C6鹵烷基羰基、Ci-C6烷氧基 羰基、(^-(:6烷基胺基羰基、C2-C8二烷基胺基羰基、 鹵烷基亞磺醯基或Ci-Ce鹵烷基磺醯基, η為0、1、2、3或4,以及 Α代表連接至-(CR6R7)m-部分的位置。 以基團 Qi、Q2、Q3、Q4、q5、q6、q7、q25、q26、q27、 Q28、Q29、Q86、Q87、Q88、Q89、Q90 更佳,且以 Ql 至 Q7 特佳。 較佳者’ R以及R,獨立地為氫、Cl-C4烷基、C丨-C4鹵 烧基、(VC4烷氧基或cvc^鹵烷氧基,以r”為氫、Ci_C4 烷基、CVC4鹵烷基、Ci-C^烷氧基、(VC4鹵烷氧基或Cl_c6 鹵烷氧基羰基。 較佳者’η為〇、1及2。 較佳者’在式(I)化合物中’ 111為1或2,最佳者,mg 1 0 某些式(I)化合物為烯類且根據習知程序進行烯類的典 型反應而得到額外的式⑴化合物。此類反應的實例包括, 但不限於,齒化反應或氫化反應。 26 201014819
其中R及R6形成鍵。 式⑴化口物(其巾r5及r6形成鍵且r7為函素(較佳為 ❹氯化物或溴化物)或RU Cl-c6院基續酸鹽(較佳為曱績酸 鹽)或cvC6齒烧基續酸鹽(較佳為三說甲確酸鹽)或芳基續 酸鹽(較佳為曱笨確酸鹽)可與合適的偶合配對於敛述於文 獻中關於铃木-宮浦(Suzuki_Miyaura)、8〇等咖及相 關交叉偶合反應之條件下進行交又偶合反應而製得額外的 式⑴化合物(參見’例如0,Brien,c及〇rgan,M G Angew
Chem. Int. Ed.(2007),46,2768-2813;Suzuki, A. Jounal of
Organometallic Chemisty (2002), 653,83; Miyaura N and ❹ Suzuki, A. Chem. Rev. (1995) 95 2457 2483)。 所屬技術領域中具有通常知識者將會理解式⑴化合物 可包含含有-或多個能夠在習知條件下被轉型成為替換取 代基的方香族部分,且這些化合物本身可作為製備額外式⑴ 化合物的中間體。 例如,式⑴化合物(其中R、r2、尺3或R4為烯基或烘 基)可在習知條件下被還原成式⑴化合物(其中r1、r2 、r3 或R4為烷基)且式⑴化合物(其中Ri、R2、…或R4為鹵素, 較佳為溴化物或碘化物)可與合適的偶合配對於敘述於文獻 27 201014819 中關於鈴木-宮浦(Suzuki-Miyaura) 、Sonogashira及相關 交叉偶合反應之條件下進行交叉偶合反應而製得額外的式 (I)化合物(參見,例如 O’Brien,C.及 Organ,M. G.Angew.
Chem. Int. Ed.(2007),46,2768-2813;Suzuki, A. Jounal of
Organometallic Chemisty (2002), 653,83; Miyaura N and Suzuki, A. Chem. Rev. (1995),95,2457-2483) °
其中G為CVCs烷基、c2-C8鹵烷基、苯基C丨-C8烷基 (其中苯基可視需要被Ci_c3烷基、Ci_c3鹵烷基、Ci_C3 烧氧基、CVC3画坑氧基、Cl_C3烷硫基、Cl-C3烷基亞磺醯 基、C^-C:3烷基磺醯基、鹵素、氰基或硝基取代)、雜芳基 Ci-cs燒基(其中雜芳基可視需要被Ci_c3烷基、鹵烷 基烧氧基、_烧氧基、炫•硫基、CVC3 烷基亞磺醯基'C^C3烷基磺醯基、鹵素、氰基或硝基取代)、 C3-C/ 稀基、C3_C8 自稀基、C3_C8 炔基、c(xa) Ra、 C(X )-X -R、C(Xd)-N(Rc)_Rd、_s〇2_Re、_p(xe)(Rf) Rg 或 CH2-X _Rh ’ 其中 xa、Xb、、χά、χβ、xf、Ra、Rb、RC、
Rd ' Re Ph_L„ *
如上述所定義之式(I)化合物可藉由將 弋()化〇物’其為其中之式⑴化合物,以試劑GZ, 其中G-Z為烷基化劑,例如烷基“烷基幽的定義包括簡 單的C! c8烧基函’例如甲基破及乙基蛾;經取代之烧基 例如其中X為氧之氣甲基烷基醚Cl_cH2_xf _Rh,及其
中為硫之氣甲基以硫CKCH2_xf_Rh)、魏C1_CJ S日或硫酸二(C C烷基) ϋ 丞曰,或以C3-C8烯基鹵;或以c3-c8 诀基齒,或以酿化劑,例如甘丄 _ 如其中X為氧之羧酸HO-C(Xa)Ra, 28 201014819 -其中Xa為氧之酸氣Cl-C(Xa)Ra,或其中Xa為氧之羧酐 [RaC(Xa)h〇,或異氰酸酯RcN=c = 〇,或胺基甲醯氣 Cl-C(Xd)-N(Re)-Rd (其中Xd為氧,而其先決條件係rc或 Rd不為氫),或硫代胺基甲醯氣cl_(xd)_N(RC)-Rd (其中 Xd為硫,而其先決條件係尺。或“不為氫),或氣基曱酸 酯Cl-C(Xb)-Xc-Rb (其中以及xc為氧),或氣基硫代甲酸 酯Cl-C(Xb)-X、Rb (其中Xb為氧及Xc為硫),或氣基二硫 代甲酸酯ci-c(xb)-XC_Rb (其中Xb及Xc為硫),或異硫代 ❹氰酸酯RCN=c=s處理;或以二硫化碳及烷基化劑;或以磷 酸化劑,例如磷醯氣C1_P(Xe)(Rf)_Rg ;或以磺酸化劑,例如 磺醯氣Cl-S〇2_Re相繼處理而製備,較佳者該處理係在至少 1當量鹼的存在下進行。 可形成式(I)異構化合物。例如,式(A)化合物可導致二 種式⑴異構化合物,或式⑴化合物的異構混合物。本發明 涵蓋二種式⑴異構化合物,以及此等化合物以任何比率之 混合物。
方法例如於US4436666所敘述。替換步驟由Pizzorno,JV[及 Alb〇nico,S.M 於 Chem. Ind.(倫敦),(1972),425 ; B〇rn,H 等人於 J. Chem. Soc., (1953),1779 ; Μ· Constantino 等人 29 201014819 於 Synth· Commun.,(1992),22 (19),2859 ; Y. Tian 等人於 Synth. Commun.,(1997),27 (9),1577 ; S. Chandra Roy 等人 於 Chem. Letters, (2006), 35 (1), 16 ; P. K. Zubaidha 等人於 Tetrahedron Lett”(2004),45,7187 以及 Zwanenburg, B 等 人於 Tetrahedron(2005),45(22),7109 所提出。 環狀 1,3-二酮類之醯化反應可由類似於那些例如於 US4551547、US4175135、US4422870、US4659372 及 US4436666所述之步驟而完成。典型地,式(A)之二酮類可 以醯化劑在至少1當量適合的鹼存在下,視需要在適合的 溶劑存在下處理。該鹼可為無機鹼,例如鹼金屬碳酸鹽或 氫氧化物,或鹼金屬氫化物,或有機鹼,例如三級胺或金 屬烷醇化物。適合的無機鹼的實例包括碳酸鈉、氫氧化鈉 或負^氧化斜、氫化納,而適合的有機驗包括三烧基胺,例 如三甲胺及三乙胺、吡啶或其他胺鹼類,例如1,4-二偶氮雙 環[2.2.2]-辛烷及1,8-二偶氮雙環[5.4.0]十一-7-烯。較佳的 鹼包括三乙胺及吡啶。適合於該反應的溶劑係選自與試劑 相容者,並包括醚類,例如四氫呋喃及1,2-二曱氧基乙烷; 及鹵化溶劑,例如二氯甲烷及氣仿。某些鹼類,例如吡啶 及三乙胺可成功地被用作鹼及溶劑二者。關於其中醯化劑 為羧酸的例子中,醯化反應較佳者在已知的偶合劑,例如 碘化2-氣-1-甲基吡錠、N,N’-二環己基碳化二醯亞胺、1-(3-二甲胺基丙基)-3-乙基碳化二醯亞胺及N,N’-碳化二醯亞胺 的存在下及視需要在鹼,例如三乙胺或吡啶的存在下於適 合的溶劑中,例如四氫呋喃、二氣甲烷或乙腈中完成。適 30 201014819 合的程序由例如 Zhang W.和 Pugh,G.於 Tetrahedron Lett., (1999),40 (43),7595 以及 Isobe,T 和 Ishikawa,T.於 J. Org. Chem. (1999),64 (19),6984 所敘述。 環狀1,3-二酮類的磷酸化反應可使用磷醯_或硫代磷 醯鹵及鹼以類似於那些由L. Hodakowski於US4409153所述 之步驟而完成。 式(A)化合物的磺酸化反應可使用烷基或芳基磺醯鹵而 達成’較佳者在至少1當量驗的存在下,以例如Kowalski,C.J ❿ 和 Fields,K,W 於 J. 〇rg. Chem”(198 1),46,197 之步驟進 行。 式(A)化合物可在習用加熱或在微波照射之下、較於25 C及1500 C之間、較佳在酸觸媒例如氫鹽酸存在下及視 需要在合適溶劑例如四氫呋喃或丙酮存在下、藉由水解製 備於式(I)化合物。
在另外方案中’式(A)化合物可經由式化合物或式(c) 化合物(其中R”’為氳或烷基)之環化反應而製備其較佳在 酸或鹼的存在下及視需要在適合的溶劑存在下,以類彳又、 那些由T. Wheeler於US4209532所述之方沐冰/ 成延行。式(B) 化合物或式(C)化合物(其中R,,’為氫)可在酸性條件, 下較佳 31 201014819 在強酸’例如硫酸、多磷酸或伊頓(Eaton )氏試劑的存在 下,視需要在適合的溶劑,例如乙酸、甲苯或二氣曱烧的 存在下進行環化。
其中R”’為烷基(較佳者為甲基或乙基)之式(B)化/ 物或式(C)化合物可在酸性或鹼性條件下較佳者在至少 當量強驗,例如三級丁醇鉀、二異丙基醢㈣或氫化紹
存在下及在溶劑(例如四氫吱淹、甲苯、二甲基亞颯或W 一甲基甲醯胺中)環化。 其中R”’為氫之式(B)化合物或式(c)化合物可在標準4 件下’在酸觸媒存在下、例如藉由與縣醇丽加熱而d 別被醋化成其巾R”’為烧基之式(B)化合物或式(c)化合物 其中R”’為氫之式(B)化合物或式(c)化合物可在㈣ ::藉由其中R’’,’,為烧基(較佳者為甲基或乙基)卿 。或式⑻化合物的醋化,接著藉由類似於那些由例如, 32 201014819
Wheeler於US4209532所述之方法酸化反應混合物,以完成
去羧基化反應而製備。
OR'
(E)
其中R’’’’為烷基之式(D)化合物及式(E)化合物可藉由分 別將式(F)化合物在鹼性條件下以適合的式(G)之羧酸氣或 ® 適合的式(H)羧酸氣處理而製備》適合的鹼包括三級丁醇 鉀、雙(二甲基矽烷基)醯胺鈉及二異丙基醯胺鋰而且反應 較佳者在適合的溶劑中(例如四氫呋喃或甲苯)以介於_8〇 °〇與3(TC之間的溫度下進行。可替換的,其中R,,”為氫之 式(D)化合物或式(E)化合物可藉由在介於_8〇它與3〇。匚之間 的溫度下、於適合的溶劑中(例如四氫呋喃或甲笨)以合 適的鹼(例如三級丁醇鉀、雙(三甲基矽烷基)醯胺鈉及二異 丙基醢胺鋰)處理式(F)化合物以及使所製得陰離子與合適 33 201014819 的式(J)的酐反應而製備。
式(F)化合物為習知化合物,或者可藉習知方法自習知 化合物加以製備。 Ο 式化合物可藉由類似於BaUini,R等人於
Synthesis(2002),(5),681-685;Bergmeier,S.C·及 Ismali,Κ· A. 於 Synthesis(2000),(10),1369-1371;Groutas,W.C 等人於了· Med. Chem.(1989),32(7),1607-ll 以及 Bernhard, K 及 Lincke, H. Helv.於 Chim.Acta (1946),19,1457-1466 中所述之方法加 以製備。 式(G)化合物或式(η)化合物可在鹼例如二甲基胺基°比 啶或鹼金屬烷醇存在下以烷基醇R”’-〇H處理式(J)化合物 34 201014819 (參見,例如 S. Buser 以及 A. Vasella,Helv. Chim. Acta, (2005), 88,3151 ; M. Hart 等人於 Bioorg. Med. Chem. Letters,(2004),14, 1969),接著在習知條件下以氣化劑例如 草醯氯或亞硫醯氯處理所得到的酸加以製備(參見,例如C. Santelli-Rouvier 於 Tetrahedron Lett·,(1984),25(39),4371 ; D. Walba 以及 Μ· Wand 於 Tetrahedron Lett”(1982),23 (48),4995; J. Cason 於 Org. Synth. Coll.Vol. III,169 (1955)。
〇 氣化劑 式(G)化合物及式(H)化合物可藉習知方法自習知化合 物加以製備。例如,得到式(G)化合物及式(H)化合物之類似 方法被敘述於 Bergmeier,S. C.及 Ismali, Κ· A.於 Synthesis (2000),(10),1369-1371。 在另外之方案中,式(I)化合物可在鹼性條件下以式(L) 化合物(其中LG為離去基例如鹵素,較佳為碘化物或溴化 物)或活性醇(較佳為甲磺酸鹽或甲苯磺酸鹽)處理式(K)化 合物而加以製備。適合的鹼包括二異丙基醯胺鈉、六曱基 二矽疊氮、三級丁醇鉀且反應較佳係在於-80°C與30°C之間 的溫度下進行。 35 201014819
式(L)化合物為習知,或可藉習知方法自習知化合物加 以製備(參見,例如W02006016178 ; Ueno, Η等人於J. Med. Chem. (2005),48(10),25 88-3604;Kanosh, S 等人於 Tetrahedron (2002),58(35),7049-7064;Strachan, J.-P 等人於 Org. Chem· (2006),71(26),9909-991 1。 式(K)化合物為習知化合物,或可藉習知方法自習知化 合物加以製備(參見,例如Song,Y. S. S等人Tetrahedron Lett,(2005),46(46),5987-5990; Kuethe, J. T 等人 Org.Chem.(2002),67(l 7),5993-6000)。 可替代的,式(K)化合物(其中G為Ci-G烷基)可在習 知條件下藉式(K)化合物(其中G為氫)的烷基化或藉由習知 方法(參見,例如 Eberhardi,U 等人,Chem· Ber. (1983),1 16(1),119-135)加以製備。 式(K)化合物(其中G為氫)為習知化合物,或可藉習知 方法自習知化合物加以製備(參見,例如Nguyen,Η. N等人 J. Am. Chem. Soc.(2003), 125(39), 1 181 8-11 8 1 9 ; Bonjoch, J 等人.Tetrahedron (2001),57(28),6011-6017 ; Fox,J. M.等人 J. Am. Chem. Soc.(2000),122(7),1360-13 70 ; US4338 122 ; US4283348) ° 36 201014819 e 可替代的,式(I)化合物(其中R5及R6形成鍵)可藉由習 知方法由式(M)化合物製備(參見,例如Nagaoka,H等人 Tetrahedron Letters(1985),26(41),5053-5056;Nagaoka,Η 等 人 J. Am. Chem. Soc(1986),108(16),5019-5021; Zuki,Μ 等 人 Bull. Chem· Soc. Japan(1988),614(4),1299-1312;Enholm, E. J 等人 J. Org. Chem.(1996),61(16),5384-5390; Clive,D. L· J 等人 Tetrahedron (2001),57(18),2845-3858 ; Bartoli,G 等 人 J. Org. Chem.(2002),67(25),9111-9114. Jung,M.E.等人 Chem. Comm. (2003),(2),196-197 ; EP1433772 ; JP2004203844 ; IN194295)。
其中R5及R6形成鍵 式(Μ)化合物可在鹼性條件下以式(N)化合物處理式(K) Q 化合物(其中R5為氫)而加以製備。適合的鹼包括二異丙基 醯胺鈉、六曱基二矽疊氮、三級丁醇鉀且反應較佳係在於-80 。(:與30°C之間的溫度及較佳在適合溶劑(例如四氫呋喃)下 進行* 37 201014819
_ 或可藉習知方法自習知化 式(N)化合物為習知化合物 合物加以製備。
式()化。物(其中G為C丨-C4烷基)可製備於式⑼化合 (其中G為c丨-c4烷基’且Hal為鹵素,較佳為溴或碘)與 () (〇ΪΙ)2芳基硼酸或芳基蝴酸酯於適合纪觸媒(例 如相對於化合物⑼為G侧至㈣乙酸師…及驗(例如相 對於化合物(〇)為i至10當量磷酸鉀)存在下、較佳在適合 配位體(例如相對於化合物(0)為0 001至50%(2二環己基 膦)-2·,6·-二甲氧基聯苯)及適合溶劑(例如曱苯或,2二甲氧 基乙烷)存在下、較佳介於25t:& 2〇{rc之間及在習知加熱 或微波照射之下反應(參見,例如S〇ng,Y.S.S等人
Tetrahedron Lett.(2005),46(46),5987-5990 ; Kuethe,J. Τ·等 人 J. Org. Chem. (2002),67(17),5993-6000)。
式(0)化合物可製備於鹵化式(Q)化合物,接著在習知條 件下以C!-CU烧基_化物或三-Ci-CU烧基原甲酸自旨燒化所得 38 201014819 式(R)鹵化物,例如藉由Shepherd R. G.等人J. Chem. Soc. Perkin Trans. 1(1987),2153-2155 及 Lin Y. -L 等人 Bioorg. Med. Chem· (2002),10, 685-690 所述程序。可替代的,式(O) 化合物可製備於以烷基鹵化物或三-Ci-C^烷基原曱酸 酯烷化式(Q)化合物,以及在習知條件下以鹵化所得式(S) 稀酮(參見,例如 Song, Y.S.S 等人 Tetrahedron Lett.(2005),46(46),5987-5990 ; Kuethe,J. Τ·等人 J. Org. Chem. (2002),67(17),5993-6000 ; Belmont,D.T 等人 JL Org. Chem· 1985,50(21),4102·4107)。
式(S)化合物可在鹼性條件下以式(L)化合物(其中LG 為離去基例如函素,較佳為碘化物或溴化物)或活性醇(較佳 為曱磺酸鹽或甲苯磺酸鹽)處理式(T)化合物而加以製備。適 合的鹼包括二異丙基醯胺鈉、六甲基二矽疊氮、三級丁醇 39 201014819 鉀且反應較佳係在於-80°C與30°C之間的溫度下及在適合 溶劑(例如四氫呋喃)中進行(參見,例如Gulias,Μ等人&呂· Lett. (2003),5(1 1),1975-1977 ; Altenbach,R. J 等人 J. Med. Chem. (2006), 49(23), 6869-6887 ; Snowden, R. L.
Tetrahedron (1986),42(12),3277-90; Oppolzer,W 等人 Helv. Chim. Acta (1980),63(4),788-92;Mellor,M 等人 Synth. Commun. 1979,9(1),1-4)。
式(T)化合物為習知化合物,或可藉習知方法自習知化 合物加以製備。 可替代的,式(S)化合物(其中R5及R6形成鍵)可藉由習 知方法由式(U)化合物製備(參見,例如Nagaoka,H等人 Tetrahedron Letters(l985),26(41 ),5053-5056;Nagaoka, Η 等 人 J. Am. Chem. Soc(1986),108(16),5019-5021; Zuki, Μ 等 人 Bull. Chem. Soc. Japan(1988),614(4),1299-1312;Enholm, E. J 等人 J· Org. Chem.(1996),61(16),5384-5390; Clive, D. L. J 等人 Tetrahedron (2001),57(18),2845-3858 ; Bartoli,G 等 人 J. Org· Chem.(2002),67(25),9111-9114. Jung,M.E.等人 Chem. Comm. (2003),(2),196-197 ; EP1433772 ; JP2004203844 ; IN194295) » 201014819
m
其中R5及R6形成鍵 式⑼化合物可在鹼性條件下M(NMb合物處理式(τ) 化°物而加m適合的驗包括二異丙基醯胺納、六甲 基·^疊氮'三級丁醇鉀錢應較佳係在於镇與賊之
間的溫度及較佳在適合溶劑(例如四氫吱鳴)下進行(參見, 例如 Aleman.
式(P)化合物可藉由習知方法製備於式(v)之芳基鹵化 ◎ 物’其中Hal為漠或蛾(參見’例如Thompson W等人j 〇rg
Chem.(1984),40, 5237 及 R. Hawkins 等人 J. Am· Chem. Soc (1960),82, 3053)。例如,式(V)之芳基鹵化物可經燒基經或 烧基鎂鹵化物於合適溶劑,較佳為二乙謎或四氫咬脅,於-80 °C與30°C之間的溫度處理,以及然後所得到的芳基鎂或芳 基鋰試劑經三烷基硼酸酯(較佳三甲基硼酸酯)反應以得到 芳烷二烷基硼酸酯,其可在酸性條件下被水解而提供式(p) 棚酸。 201014819
1. 烷基鋰或格納德 2. 三烷基硼酸鹽 3. H30+ fommtoi (V)
可替代的,式(v)化合物可與衍生自12或丨,3-烷二 醇,例如頻哪醇(pinacol)、2,2·二甲基_13·丙二醇以及2甲 基-2’4-戊二醇的環硼酸酯在習知條件下反應(參見,例如 Miyaura N.等人 J· 0rg. Chem. (1995),6〇 75〇8 及 zhu w 等人
Org. Lett· (2006),8(2),261) ’且所得硼酸酯可在酸性條件下 被水解而得到式(P)硼酸。 式(V)之芳基鹵化物係為習知,或者可藉習知方法自習 知化合物加以製備。例如,式(v)的芳基齒化物可從式(w) 之苯胺經由對應之重氮鹽以習知方法(例如山德梅爾 (Sandmeyer)反應)加以製備。
式(W)之苯胺係為習知,或者可藉習知方法自習知化合 物加以製備。 可替代的,式(V)之化合物可藉相對應習知化合物藉習 知方法加以製備。 式(Q)化合物可藉水解製備於式(s)化合物,其較佳在酸 觸媒例如氩氣酸存在下,以及視需要在合適溶劑例如四氫 °夫%或丙酮存在下’較佳在介於25〇C及l5〇t之間於傳 42 201014819 統加熱或在微波照射下進行。
可替換的,式(Q)化合物可藉由習知方法製備於習知化 合物(參見 Manukina,T 等人 Zhurnal Organicheskoi Khimii (1986),22(4),873_4; Mellor,Μ.等人.Synth. Commun. 1979,9(l),l-4)。 在另外方案中,式(A)化合物可製備於使式(Q)化合物與 合適的芳基鹵化物(例如芳基-碘化物、芳基-溴化物或芳基-氯化物),式(V)之Ar-Hal,或合適的CrCe烷基磺酸鹽(較 佳為甲磺酸鹽)或鹵烷基磺酸鹽(較佳為三氟甲磺酸鹽) 或芳基磺酸鹽(較佳為甲苯磺酸鹽),於合適鈀觸媒(例如相 對於式(Q)化合物0.001至50%乙酸鈀(II)及鹼(例如相對於 式(Q)化合物1至10當量磷酸鉀)存在下,以及較佳在合適 配位體(例如相對於式(Q)化合物0.001至50%(2-二環己基 膦)-2',4’,6’-三異丙基聯苯)存在下,以及在合適溶劑(例如二 噁烷或1,2-二甲氧基乙烷)中,較佳介於25°C及200°C之間 反應。類似偶合反應在文獻中係習知者(參見,例如Belmont, D.T.等人 J. Org. Chem. 1985,50(21),4102-4107; Fox,J. Μ. 等人· J. Am. Chem. Soc.(2000),122(7),1360-1370;B. Hong 等人.WO 2005/000233)。可替代的,式(A)化合物可製備於 使式(Q)化合物與合適的芳基鹵化物(例如芳基-碘化物)’式 43 201014819 (V)之Ar-Hal,於合適銅觸媒(例如相對於式(Q)化合物0_001 至50%碘化銅(I)及鹼(例如相對於式(Q)化合物1至10當量 碳酸鉀)存在下,以及較佳在合適配位體(例如相對於式(Q) 化合物0.001至50%L-脯胺酸)存在下,以及在合適溶劑(例 如二甲基亞颯)中,較佳介於25°C及200°C之間反應。類似 偶合反應對芳基鹵化物之文獻中係習知者(參見,例如Jiang, Y.等人 Synlett (2005),18,2731-2734)。
觸媒,配位體 R* 鹼,溶劑 (V) (A) 額外式(A)化合物可製備於式(Q)化合物與式(X)之有機 錯試劑在敘述於例如 Pinhey, J. Pure and Appl· Chem. (1996),68(4),819 及 Moloney Μ·等人 Tetrahedron Lett.(2002),43,3407中之條件下反應。
式(X)之有機鉛試劑可製備於式(P)硼酸,式(Y)錫烷(其 中R””’為Ci-C4烷基),或式(Ζ)化合物與四乙酸鉛根據習知 44 201014819 程序之直接船酸鹽化(plumbation)。
Pb(〇AcJ 寿
(?) 另外式(A)化合物可製備於式(Q)化合物與合適的三芳 基祕化合物於例如Fedorov, A. U等人Russ. Chem· Bull. Int. Ed.(2005),54(l 1),2602 以及 Koech Ρ·等人 J. Am. Chem. Soc. (2004),126( 17),5 3 50及其中參考文獻之條件下之反應。 額外式(A)化合物可製備於式(AA)之蛾内鏽(iodonium ylide)(其中Ar為視需要經取代的苯基)及式(P)之芳基硼酸 於合適鈀觸媒、鹼之存在下及合適溶劑中之反應。
合適的鈀觸媒大致上為鈀(II)或鈀(0)錯合物,例如二鹵 化鈀(II)、乙酸鈀(II)、硫酸鈀(II)、雙(三苯基膦)-二氯化鈀 (II)、雙(三環戊基膦)二氯化鈀(II)、雙(三環己基-膦)二氯化 45 201014819 鈀(π)、雙(二苯亞基丙鲷)鈀(0)或四(三苯基膦)鈀(〇)。鈀觸 ' 媒亦可藉由與所欲配位體原地製備於鈀(π)或鈀(〇)化合物 與所欲配位體,例如藉由混合鈀(π)鹽至即將被錯合之者, 例如二氣化鈀(II)(PdCl2)或乙酸鈀(II)(Pd(0Ac)2),與所欲配 位體,例如二笨基膦(pph3),三環戊基膦,三環己基膦,2_ —環己基膦基-2’-6’-二甲氧基聯苯或2_二環己基膦基 -2,4’,6’-三異丙基聯苯及所選定溶劑,與式(AA)化合物、 式(P)芳基硼酸及鹼。亦合適的二配位配位體例如為丨丨,雙 (二苯基麟基)苐或1,2-雙(二苯基膦基)乙烷。藉由加熱反應 ❹ 媒介,因此原地形成C-C偶合反應所欲之鈀(11)錯合物或鈀 (0)錯合物’以及然後起始C_C偶合反應。 把觸媒被使用之數量為自0.001至50莫耳% ,較佳數 量為自0.1至15莫耳%,係以式(AA)化合物為基準。反應 亦可在其他添加劑存在下進行,添加劑例如為四烷基銨 鹽,諸如四丁基溴化銨。較佳者,鈀觸媒為乙酸鈀,鹼為 氫氧化鋰以及溶劑為水性1,2_二甲氧基乙烧。 式(AA)化合物可製備於式(Q)化合物,其係藉由高價試 ◎ 劑例如(二乙醯氧基)碘苯或氧碘基苯及鹼例如水性碳酸 納、氫氧化鐘或氫氧化納於溶劑例如水或水性醇例如水性 乙醇處理’其係根據Schank K等人Synthesis (1983) 392
Moriarty R. Μ 等人 J. Am. Chem. Soc. (1985),1〇7,1375 戍
Yang Z.等人 〇rg. Lett. (2002),4(19),3333 中之程序進行。 46 201014819
額外的式(A)化合物可製備於在酸性條件下藉由式(AB) 化合物或式(AC)化合物的頻哪醇(pinacol)(其中為 C1-C4烷基(較佳為甲基))重排作用(參見,例如Eberhardt,U 等人 Chem. Ber.(1983),1 16(l),119-35 及 Wheeler,T.N.
US4283348) °
式(AB)化合物及式(AC)化合物可藉由在酸(例如四氯化 鈦或碘化鎂)存在下、視需要在合適溶劑中(例如二氣甲烷) 於介於-80°C及30°C以式(AE)化合物處理式(AD)化合物而 製備(參見,例如 Li,W.-D.Z 及 Zhang,X.-X.Org. Lett. (2002),4(20), 3485-3488; Shimada, J·等人 J. Am. Chem. Soc.(l 984), 106(6), 1759-73; Eberhardt, U 等人 Chem. Ber.(1983),116(1), 119-35 及 Wheeler, T.N. US4283348)。 47 201014819
R9 Η2
化合物(AD)係習知者或可者可藉由習知方法自式(V) 化合物或式(Z)化合物加以製備。
式(AE)化合物可在氣三-q-C^烷基矽烷基及金屬(較佳 為鈉)存在下、於合適溶劑(例如曱苯或二乙醚)中、於介於 20°C及150°C之間製備於式(AF)化合物(其中R”’為烷基(較 佳為甲基))(參見,例如 Blanchard,A. N &Burnell,D.J. Tetrahedron Lett· (2001),42(29), 4779-4781 及 Salaun,J·等 人 Tetrahedron (1989),45(10),3 151-62)。
Q
R 48 201014819 式(AF)化合物係類似於式(Η)化合物及式(G)化合物,且 可藉類似於式(H)化合物及式(G)化合物所述習知方法加以 製備。 額外的式(I)化合物(其中R5及R6形成鍵且R7及R7為 CJ-C6烷基磺酸鹽(較佳為甲磺酸鹽)或CrCe鹵烷基磺酸鹽 (較佳為三氟甲磺酸鹽)或芳基磺酸鹽(較佳為曱苯磺酸鹽)) 可依照習知程序(Specklin 等人 J. Org. Chem. 2008,73( 19),7845-7 848)製備於式(AG)化合物。
(AG)
其中R5及R6形成鍵 式(AG)化合物可在鹼性或酸性條件下製備於式(AH)化 合物。例如參見 G. Quinkert 等人 Helv. Chim. Acta, 1986, ❹ 69(3),469-537 之程序。
式(AH)化合物可製備於式(K)化合物(其R5為氫)與式 (AJ)酸氣化物於鹼存在下之反應而製備。 49 201014819
R* 式(AJ)化合物為習知者啖 ^ 4可藉習知方法自習知化合物 加以製備。 可替代的,式(AG)化合物可6„ 切可自式(M)化合物使用習知氧 C. Martin J. Org. Chem. ❹ 化程序(參見’例如D_ B. Dess及j 1983, 48 (22),4155-4156)加以製備
Ra
R* ❹ 根據本發明的式⑴化合物可以如合成法中所獲得的未 經修佛之形式被用作除草劑’但是彼等通常以各種方式使 '例如載劑、溶劑及表面活性物質而調配成除 草組。物。調配物可具有各種物理形式,例如具有粉劑、 凝膠'可濕性粉劑、水分散性顆粒、水分散性錠劑、泡騰 壓製錠劑、可乳化濃縮劑、可微乳化濃縮劑、纟包油型乳 50 201014819 ' 液、油懸劑、水性分散劑、油性分散劑、懸乳劑、膠囊懸 浮劑、可乳化顆粒、可溶性液體、水溶性濃縮劑(具有水 與水互溶之有機溶劑作為載劑)、浸潰型聚合物膜的型式 或從例如1999年的第5版植物保護產品的發展及fa〇規格
的使用手冊(Manual on Development and Use of FAO
Specifications for Plant Protection Products )已知的其他型 式。該等調配物可直接被使用或在使用之前被稀釋。稀釋 之調配物可以例如水、液體肥料、微營養素、生物有機體、 φ 油或溶劑製備。 調配物可以例如藉由將活性成分與調配佐劑混合而製 備,以便獲得具有細碎的固體、顆粒、溶液、懸浮液或乳 液型式的組合物。活性成分也可與其他佐劑調配,例如細 碎的固體、礦物油、植物油、修飾之植物油、有機溶劑、 水、表面活性物質或其組合。活性成分也可包括在由聚人 物所組成的非常細微膠囊中。微膠囊包括在多孔載劑中的 活性成分。該載劑能夠使活性成分以受控制的量释放至其 Ο 周圍中(例如,緩慢釋放)。微膠囊經常具有從〇. 1至 微米的直徑。彼等包括具有以膠囊重量計從約25至95%之 量的活性成分。活性成分可以單片固體形式、在固邀或液 體分散劑中的粒子形式或適合的溶液形式存在。封膠膜包 含例如天然及合成膠、纖維素、笨乙烯-丁二烯共聚物、聚 丙烯腈、聚丙烯酸酯、聚酯、聚醯胺、聚尿素、聚胺基甲 酸醋或化學修飾之聚合物及黃原酸殿粉或熟習所屬相關技 術領域者已知的其他聚合物。或者,有可能形成其中活性 51 201014819 成分以細碎的粒子形成存在於基底物質的固體基質中的非 --常細微膠囊’但是在該例子中,微膠囊未經封膠。 , 適合於製備根據本發明的組合物的調配佐劑就其本身 而言為已知的。可使用下列者作為液體载劑:水、甲苯、 一甲本、石油謎、植物油、丙嗣、甲乙_、環己_、酸奸、 乙腈、乙酿苯、乙酸戍酯'2-丁酮、碳酸丁烯酯、氣苯、環 己烧、環己醇、乙酸之烷酯、二丙酮醇、丨,2_二氣丙烷、二 乙醇胺、對-二乙苯、二乙二醇、松脂酸二乙二醇酯、二乙 一醇丁醚、二乙二醇乙醚、二乙二醇曱醚、N,N_:曱基甲 ^ 酿胺、二甲基亞艰、1,4-二嗯烧、二丙二醇、二丙二醇甲謎、 一苯甲酸一丙二醇醋、二普西托(diproxit〇i )、烧基〇比洛 咬嗣、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、ι,ι,i-三氣乙 烧、2-庚酮、α_蒎烯、心葶、乳酸乙酯、乙二醇、乙二酵 丁謎、乙二醇甲醚、1Τ -丁内酯、甘油、乙酸甘油酯、二乙 酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸異戊酯、 乙酸異莰酯、異辛烷、異佛酮、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、曱基異戊酮、 〇 甲基異丁酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲 燒 間-一曱笨、正-己烧、正-辛胺、十八烧酸、乙酸辛胺 醋、油酸、油胺、鄰-二甲苯、酚、聚乙二醇(PEG 400 ) ' 丙酸、乳酸丙酯、碳酸丙烯酯、丙二醇、丙二醇甲醚、對-二甲笨、曱苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石 壤、礦物油、三氣乙烯、過氣乙烯、乙酸乙酯、乙酸戊酯、 乙酸丁酯、丙二醇甲醚、二乙二醇甲醚、甲醇、乙醇、異 52 201014819 丙醇及較高分子量醇m 辛醇、乙-醢 j如戍醇、四氫呋喃醇、己醇、 —醇、丙二醇、甘 物。水通當县接雄‘ 曲、曱基_2_吡咯啶酮與類似
疋稀釋浪縮劑的I 例如滑石粉、二童 4幻戰劑選擇。適合的固體載劑為 泡石黏土、矽藻土、石六蠟石黏土、二氧化矽、鎂鋁海 綿籽殼、小麥粉、大::石、碳酸約、膨土、㈣脫石、 木質素及類似的材料,例如::、木粉、研磨之核桃殼、 所述。 j如例在 CRF 180.1001. (c) & (d)中 大多數表面活性物皙姑 _ ., 貝被:有利地用在固體及液鱧調配物 一 中’尤其在那班1在俊用 ,^ 、 —彳更用之前可以載劑稀釋的調配物 *活11物質可為陰離子陽離子非離子或聚合物, 、被用作乳化'濕潤或懸浮劑或其他目的。典型的表面活 性物質包括例如貌基硫酸 吸t鹽類,例如月桂基硫酸二乙醇 ❿ 錢烷芳基磺奴之鹽類,例如十二烷基苯磺酸鈣;烷酚環 氧烷烴加成產物’例如壬酚乙氧基化合物丨醇-環氧烷烴加 成產物,例如二癸醇乙氧基化合物;皂類例如硬脂酸鈉; 烧萘續酸之鹽類,例如二丁蔡績酸納;績基丁二酸鹽之二 烷酯,例如二(2-乙己基)磺基丁二酸鈉;山梨醇酯,例如油 酸山梨醇酯’·四級胺,例如氣化月桂基三甲基銨;脂肪酸 之聚乙二醇酯’例如聚硬脂酸乙二醇酯;環氧乙烷與環氧 丙烷之嵌段共聚物;及單-及二_烷基磷酸酯之鹽類;及也在 例如紐澤西州Ridgewood之MC出版公司於1981年之” McCutcheon s Detergents and Emulsifiers Annuals” 中所 述之另外的物質。 53 201014819 經常可用在殺害蟲調配物中的更多佐劑包括結晶抑制 劑、黏度修飾物質、懸浮劑、染料、抗氧化劑、起泡劑、 光吸收劑、混合輔助劑、除泡劑 '複合劑、中和或pH_修飾 物質與緩衝劑、腐蝕抑制劑、香料、濕潤劑、吸收改良劑、 微營養素、增塑劑、助滑劑、潤滑劑、分散劑、增稠劑' 抗冷凝劑、微生物殺菌劑及也為液體與固體肥料。
〇 調配物也可包含額外的活性物質,例如更多的除草 劑、除草劑安全劑、植物生長調節劑、殺真菌劑或殺尾蟲 劑。根據本發明的組合物可另外包括含有植物或動物來源 之油、礦物油'該等油的烷酯或該等油及油衍生物之混合 物的添加劑。在根據本發明的組合物中所使用的添加劑之 量通常係以喷霧混合物為基準計從0 01至1〇%。例如,在 已製備好噴霧混合物之後’可將油添加劑以所欲之濃度加 入喷霧槽中》較佳的油添加劑包含礦物油或植物來源之 油’例如油菜籽油、橄欖油或向日葵油;乳化之植物油, 例如 AMIGO® ( Rh0ne-P〇ulenc Canada Inc );植物來源之 油的烷酯,例如甲基衍生物,或動物來源之油的烷酯例 如魚油或牛肉脂。較佳的添加劑包括例如基本上8〇重量% 之魚油之烷酯& 15 *量%之甲基化油菜籽油作為活性組 伤並也包括5重量%之習知的乳化劑及修飾劑。尤其 佳的油添加劑包含c8-C22脂肪酸之烷醋,尤其為Ci2_Ci8脂 肪酸之甲基衍生物’例如月桂酸、棕櫚酸及油酸之甲醋為 重要的添加劑。那些醋已知為月桂酸甲s|(cas⑴_82 〇)、 棕櫚酸甲醋(cAS-112-39_0)及油酸甲醋(CAS112·62 9)。 54 201014819 較佳的脂肪酸甲酯衍生物為Emery® 2230及223 1 ( C〇gnis GmbH )。那些及其他的油衍生物也從南伊利諾大學於2〇时 年的第 5 版之 Compendium of Herbicide Adjuvants 已知。 油添加劑的施予及作用可藉由將彼等與表面活性物 質’例如非離子、陰離子或陽離子界面活性劑組合而進一 步改進。適合的陰離子、非離子及陽離子界面活性劑的實 例陳列在WO 97/34485的第7及8頁中。較佳的表面活性 物質為十二烷基苯磺酸鹽類型,尤其為其鈣鹽之陰離子界 ® 面活性劑,並也為脂肪醇乙氧基化合物類型之非離子界面 活性劑。特別優先選擇具有從5至40之乙氧基化程度之乙 氧基化Cu-C22脂肪醇。市售可取得的界面活性劑的實例為
Genapol類型(ciariant AG ) ^也較佳的是聚矽氧界面活性 劑,尤其為聚烷基氧化物修飾之七甲基三矽氧烷,其為市 售可取得的例如SilwetL_77(g),並也為全氟化界面活性劑。 與總添加劑有關的表面活性物質之濃度通常從」至3〇重量 /6由油或礦物油或其衍生物與界面活性劑之混合物所組 參成的油添加劑的實例$ Eden〇r ME su@、加咖rge⑧ (snygenta AG,CH)及 Actipr〇n⑧(BP 〇il UK Limite(i GB)。 ’ 該表面活性物質也可單獨用在調配物中,換言之,沒 有油添加劑。 入油添加劑/界面活性劑混合物中的有機溶 劑可貢獻另外的作用拗afe A ,. 曰金性。適σ的溶劑為例如S〇ivesso⑧ (ESSO )及 Aromatic Slni , _ mauc s〇lvent® ( Εχχ〇η 公司)^ 該等溶劑 55 201014819 的濃度可以總重量計從10至80重量%。可與溶劑摻合的 該等油添加劑的濃度被欽述在例如US-A-4 834 908中。在 本文所揭示之市售可取得的油添加劑係以名稱MERGE® (BASF公司)已知。根據本發明較佳的另外的 油添加劑為 SCORE® ( Syngenta Crop Protecti〇n Canada)。 除了上述所列之油添加劑之外,為了增強根據本發明 的組合物之活性,故也有可能將烷基吡咯啶酮之調配物(例 如,Agrimax® )加入喷霧混合物中。也可使用合成乳膠之 調配物,像是例如聚丙稀醯胺、聚乙烯基化合物或聚·丨_對_ 孟烯(例如’ Bond®、Courier®或Emerald®)。包括丙酸 之溶液,例如Eurogkem Pen-e-trate®也可混合至喷霧混合 物中,作為活性增強劑。 除草調配物通常包從0.1至99重量%,尤其從〇.1至 95重量%之式ϊ化合物及從1至99 9重量%之調配佐劑, 其較佳地包括從〇至25重量%之表面活性物質。然而,市 售商品較佳地被調配成濃縮劑,而最終使用者一般係使用 稀釋的調配物。 式I化合物的施予率可在寬廣的限度内改變,並依據土 壤性質、施予方法(萌芽前或後、種子披覆、施予種溝、 非耕種作物上的施予等)、作物植物、欲控制之雜草或禾 草、當時的氣候條件及由施予方法、施予時間與標的作物 所支配的其他因素而定。根據本發明的式I化合物通常以i 至2000公克/公頃之施予率施予,較佳1至looo公克/ 公頃以及最佳在1至500公克/公頃。 56 201014819 較佳的調配物尤其具有下列組合物: (% =重量百分比) 可乳化濃縮劑: 活性成分: 1至95%,較佳地為60至90% 表面活性劑: 1至30%,較佳地為5至20% 液體載劑: 1至80%,較佳地為1至35% 粉劑: 活性成分: 0.1至10%,較佳地為1至35%
固體載劑: 99.9至90%,較佳地為99.9至99% 懸浮濃縮劑: 活性成分: 5至75%,較佳地為10至50% 水: 94至24%,較佳地為88至30% 表面活性劑: 1至40%,較佳地為2至30% 可濕性粉劑: 活性成分: 0.5至90%,較佳地為1至80% 表面活性劑: 0.5至20%,較佳地為1至15% 固體載劑: 5至95%,較佳地為15至90% 顆粒· 活性成分: 0_1至30%,較佳地為0.1至15% 固體載劑: 99.5至70%,較佳地為97至85% 下列的實施例進一 步說明 、但不是限制本發明 J 0 F 1.可乳化濃縮劑 a) b) c) d) 活性成分 5% 10% 25% 50% 十二烷基苯磺酸鈣6% 8% 6% 8% 57 201014819 蓖麻油聚乙二醇醚4% (36莫耳之環氧乙烷) 4% 4% 辛酚聚乙二醇醚 -(7-8莫耳之環氧乙烷) 4% 2% NMP - 芳香族烴混合物 10% 20% C9-C12 85% 78% 55% 16% 任何所欲濃度之乳劑可從該濃縮劑藉由以水稀釋而製 備0 F2.溶液 a) b) c) d) 活性成分 5% 10% 50% 90% 1-甲氧基-3-(3-甲氧 基丙氧基)-丙烧 - 20% 20% - 聚乙二醇MW 400 20% 10% - NMP - - 30% 10% 芳香族烴混合物 C9-C 1 2 75% 60% - 該溶液適合以微滴形式施予 0 F3.可濕性粉劑 a) b) c) d) 活性成分 5% 25% 50% 80% 木質績酸納 4% - 396 月桂基硫酸鈉 2% 3% - 4% 二異丁基萘磺酸鈉 6% 5% 6% 辛酚聚乙二醇醚 - 1% 2% 58 201014819
(7-8莫耳之環氧乙烷) 高分散性矽酸 1% 3% 5% 10% 高嶺土 88% 62% 35% . 將活性成分與,佐劑徹底混合及將混合物在適合的磨碎 機中徹底研磨,得到可濕性粉劑 ',其可以水稀釋,得到任 何所欲濃度的懸浮劑。 F4.包膜顆粒 a) b) c) 活性成分 0.1% 5% 15% 高分散性碎酸 0.9% 2% 2% 無機載劑 99.0% 93% 83 (直徑0 · 1 -1毫米) ,例如 CaC03 或 Si〇2 將活性成分溶解在 二氣甲烷中, 將溶液喷霧在載劑上 及接著將溶劑在真空中蒸發。 F5.包膜顆粒 a) b) c) 活性成分 0.1% 5% 15% 聚乙二醇MW 200 1.0% 2% 3% 高分散性碎酸 0.9% 1% 2% 無機載劑 98.0% 92% 80% (直徑0.1-1毫米) ’例如 CaC〇3 或 Si〇2 將細研磨之活性成分在混合器中均勻地塗覆於以聚乙 二醇弄濕的載劑上。以該方式獲得無粉塵之包膜顆粒。 F6.擠壓器顆粒 a) b) c) d) 59 201014819 活性成分 0.1% 3% 5% 15% 木質磺酸鈉 1.5% 2% 3% 4% 羧甲基纖維素 1.4% 2% 2% 2% 高嶺土 97.0% 93% 90% 79% 將活性成分與佐劑混合及研磨, 並將混合物以水弄 /"、。將所得混合物擠壓及接著在空氣流中乾燥。 F7.粉劑 a) b) c) 活性成分 0.1% 1% 5% 滑石 39.9% 49% 35% 高嶺土 60.0% 50% 60% 即用型粉劑係藉由將活性成分與載劑混合及在適合的 磨碎機中研磨混合物而獲得。 F8.懸浮濃縮劑 a) b) c) d) 活性成分 3% 10% 25% 50% 乙二醇 5% 5% 5% 5% 辛酚聚乙二醇醚 (15莫耳之環氧 乙烷) 1% 2% 木質磺酸鈉 3% 3% 4% 5% 羧甲基纖維素 1% 1% 1% 1% 3 7 %曱媒水溶液 0.2% 0.2% 0.2% 0.2% 聚矽氧油乳液 0.8% 0.8% 0.8% 0.8% 水 87% 79% 62% 38% 將細研磨之活性成分與佐劑緊密混合,得到懸浮濃縮 劑,可藉由以水稀釋而從該濃縮劑製備任何所欲濃度之懸 201014819 浮劑。 毋 本發明也關於一種選擇性控制在有用植物之作物中的 禾草及雜草之方法’其包含以式I化合物處理有用植物或在 栽種下的面積或其所在地。 其中可使用根據本發明的組合物的有用植物之作物包 括特別是毅類’尤其是大麥、小麥、稻米、玉米、油菜、 甜菜、甘蔗、大豆、棉、向曰葵、花生以及農園作物。 應瞭解術語'"作物〃也包括由於習知的繁殖或基因工 ❹ 程方法而成為耐受於除草劑或除草劑類別(例如,ALS、 GS、EPSPS、PPO、以及HPPD抑制劑)之作物。已藉由習 知的繁殖方法而成為耐受於例如味嗤嗣,例如甲氧味草 煙(imazamox )之作物的實例為 Clearfield®夏日油菜 (Canola )。已藉由基因工程方法而成為耐受於除草劑之作 物的實例包括例如抗嘉破塞(glyphosate )及抗固殺草 (glufosinate )之粟米變種,其以商標名稱R0un<hipReady® 及LibertyLink®可於市場上取得。欲控制之雜草可為單子葉 Φ 及雙子葉雜草二者,例如例繁縷屬(Stellaria)、豆瓣菜屬 (Nasturtium)、剪股穎屬(Agrostis)、馬唐屬(Digitaria)、 燕麥屬(Avena)、狗尾草屬(Setaria)、白芥屬(Sinapis)、黑麥 草屬(Lolium)、蘇屬(Solanum)、稗屬(Echinochloa) ' 薦 草屬(Scirpus)、雨久花屬(Monochoria)、慈姑屬(Sagittaria)、 麥屬(Bromus )、看麥娘屬(Alopecurus)、蜀黍屬(Sorghum)、 羅氏草屬(Rottboellia )、莎草屬(Cyperus)、白麻屬 (Abutilon)、黃花捻屬(Sida)、蒼耳屬(Xanthium)、莧屬 61 201014819 (Amaranthus)、餐屬(Chenopodium)、番薯屬(Ipomoea)、菊 * 屬(Chrysanthemum )、豬块硖屬(Galium)、堇菜屬(Viola) 及婆婆納屬(Veronica)。控制單子葉雜草,特別是剪股穎屬、 燕麥屬、狗尾草屬、黑麥草屬、稗屬、麥屬、看麥娘屬以 及蜀黍屬,非常廣泛。 也應瞭解作物為那些藉由基因工程法而成為對抗有害 昆蟲的作物,例如,Bt粟米(對抗歐洲玉米模(corn borer ))、
Bt棉(對抗棉鈴象鼻蟲(boll weevil))及也為Bt馬铃薯 (對抗科羅拉多甲蟲(Colorado beetle ))。Bt粟米的實例 _ 為NK®之Bt-176粟米混種(Syngenta Seeds) 。Bt毒素為 蘇力菌(Bacillus thuringiensis ) 土壤細菌天然形成的蛋白 質。毒素及能夠合成該等毒素之轉基因植物的實例被敘述 在 EP-A-451 878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073 及 EP-A-427 5 29 中。包括編碼昆 蟲抗性及表現一或多種毒素的一或多種基因的轉基因植物 的實例為 KnockOut® (粟米)、Yield Gard® (粟米)、 NuCOTIN33B® (棉)、Bollgard® (棉)、NewLeaf® (馬 〇 鈴薯)、NatureGard®及Protexcta®。植物作物及彼之種子 材料可對抗除草劑,且同時也可對抗昆蟲取食(A堆疊式" 轉基因品項)。種子可以,例如,具有表現殺昆蟲活性Cry3 蛋白質的能力,且同時耐受於嘉磷塞。應瞭解術語 '"作物" 也包括由於的習知的繁殖或基因工程方法,包括又稱為出 產特性的方法(例如,經改進之氣味、貯存穩定性、營養 素含量)所獲得的作物。 62 201014819 . 應、瞭解在栽種下的面積包括農作植物已生長之土地與 意圖栽種該等作物植物的土地。 根據本發明的式丨化合物也可與其他的除草劑組合使 用。。較佳地,在這些混合物中,式〗化合物為那些在下列 表1至102中所列之化合物中之一。式j化合物的下列混合 物特別重要: 式I化合物+乙草胺(acet〇chl〇r)、式I化合物+三 氟羧草醚(acifluorfen )、式I化合物+三氟羧草醚_鈉、式 Ο 1化合物+苯草醚(aclonifen )、式I化合物+丙烯醛 (acrolein)、式I化合物+拉草(aiachi〇r)、式I化合物 +枯殺達(alloxydim )、式I化合物+烯丙醇、式I化合物 +草殺淨(ametryn )、式I化合物+胺唑草酮 (amicarbazone)' 式 I 化合物 + 磺胺磺隆(amidosulfuron)、 式I化合物+二氯胺基〇比咬酸(aminopyralid )、式I化合 物+阿米托(amitrole)、式I化合物+胺基磺酸銨、式I 化合物+、;多稗填(anilofos )、式I化合物+亞速爛(asulam)、 參 式I化合物+草脫淨(atrazine)、式I化合物+艾維激素 (aviglycine )、式 I 化合物 + 草芬定(azafenidin)、式 I 化合物+阿日姆沙風(azimsulfurone )、式I化合物+ BCPC、 式I化合物+畢氟布它密德(beflubutamid)、式I化合物 +草除靈(benazolin )、式 I化合物+倍卡貝容 (bencarbazone)、式 I 化合物 + 倍尼芬(benfluralin)、 式I化合物+倍氟沙特(benfuresate )、式I化合物+免速 隆(bensulfuron)、式I化合物+免速隆-甲基、式I化合 63 201014819 - 物+地散構(bensulide )、式I化合物+滅草松(bentazone )、 · * 式I化合物+雙苯嘴草明(benzfendizone )、式I化合物+ 倍柔畢塞隆(benzobicyclon)、式I化合物+倍柔分奈普 (benzofenap)、式I化合物+必芬諾(bifenox)、式I化 合物+雙丙胺膦(bilanafos )、式I化合物+雙草醚 (bispyribac )、式I化合物+雙草謎-納、式I化合物+棚 砂(borax)、式I化合物+克草(bromacil)、式I化合物 +漠丁草胺(bromobutide )、式I化合物+溴分諾希姆 (bromofenoxim )、式 I 化合物+溴苯亞琐酸鹽 ⑬ (bromoxynil )、式 I 化合物 + 丁基拉草(butachlor )、式 I化合物+布它分奈希爾(butafenacil)、式I化合物+布 它密服斯(butamifos )、式I化合物+ 丁樂靈(butralin )、 式I化合物+布托西定(butroxydim )、式I化合物+ 丁草 特(butylate )、式 I 化合物 + 二甲基胂酸(cacodylic acid )、 式I化合物+氣酸鈣、式I化合物+凱分司托爾 (cafenstrole )、式 I化合物 + 雙醯草胺(carbetamide )、 式I化合物+克繁草(carfentrazone )、式I化合物+克繁 ❹ 草乙基、式I化合物+ CDEA、式I化合物+ CEPC、式I 化合物+整形醇(chlorflurenol )、式I化合物+整形醇-甲基、式I化合物+克洛達柔(chloridazon )、式I化合物 +氣嘴續隆(chlorimuron )、式I化合物+氣嘴續隆-乙基、 式 I 化合物+氣基乙酸、式 I化合物+綠麥隆 (chlorotoluron )、式 I 化合物 + 氣苯胺靈(chlorpropham )、 式I化合物+綠績隆(chlorsulfuron )、式I化合物+二甲 64 201014819
* 基氯酞酸(chlorthal )、式I化合物+二甲基氯敌酸-二甲 基、式I化合物+吲哚酮草酯(cinidon )-乙基、式I化合 物+環庚草醚(cinmethylin )、式I化合物+西速隆 (cinosulfuron)、式 I化合物 + 咯草隆(cisaniHde)、式! 化合物+勉草同(clethodim )、式I化合物+可洛丁那福普 (clodinafop)、式I化合物+可洛丁那福普-丙炔基、式j 化合物+異惡草酮(Clomazone )、式I化合物+克普草 (clomeprop)、式 I 化合物 + 畢克草(cl〇pyralid)、式 I ❹ 化合物+可洛拉蘇蘭(cloransulam)、式I化合物+可洛拉 蘇蘭-甲基、式I化合物+ CMA、式I化合物+ 4-CPB、式I 化合物+ CPMF、式I化合物+ 4-CPP、式I化合物+ CPPC、 式I化合物+甲盼、式I化合物+庫密路若(cuniyluron )、 式I化合物+氰胺(cyanamide )、式I化合物+氰乃淨 (cyanazine)、式I化合物+環草特(CyCi〇ate )、式I化 合物+環丙,績隆(cyclosulfamuron)、式I化合物+環殺 草(cycloxydim)、式I化合物+赛伏草(Cyhalofop )、式 〇 1化合物+赛伏草-丁基、式I化合物+ 2,4-D、式I化合物 + 3,4-DA、式I化合物+殺草隆(daimuron)、式I化合物 +得拉本(dalapon)、式I化合物+邁隆(daz〇met)、式 I化合物+ 2,4_DB、式I化合物+ 34_DB、式j化合物+ 2,4-DEB、式I化合物+甜菜安(desmedipham)、式j化合 物+狄斯密退恩(desmetryn )、式I化合物+殺草畏 (dicamba)、式 I化合物 + 二氣苯睛(dichl〇benil)、式 I 化合物+鄰-二氣苯、式j化合物+對-二氣苯、式I化合物 65 201014819 +滴丙酸(dichlorprop )、式I化合物+滴丙酸-P、式I化 合物+禾草靈(diclofop )、式I化合物+禾草靈-甲基、式 I化合物+雙氣績草胺(diclosulam)、式I化合物+野燕 枯 (difenzoquat )、式 I 化合物+曱硫野燕枯 (difenzoquat-metilsulfate )、式 I 化合物 + 此°比草胺 (diflufenican )、式 I 化合物+狄氟陸分柔皮 (diflufenzopyr)、式 I化合物 + 惡唾隆(dimefuron)、式 I化合物+略草丹(dimepiperate )、式I化合物+狄麥赛可 樂(dimethachlor )、式 I化合物+狄麥赛密退恩 ❹ (dimethametryn )、式 I 化合物 + 汰草滅(dimethenamid )、 式I化合物+汰草滅-P、式I化合物+穫萎得(dimethipin )、 式 I化合物+二曱基胂酸、式 I化合物+撻乃安 (dinitramine )、式 I化合物 + 狄諾特伯(dinoterb )、式 I 化合物+大芬滅(diphenamid )、式I化合物+異丙淨 (dipropetryn)、式I化合物+敵草快(diquat)、式I化 合物+敵草快二漠化物、式I化合物+汰硫草(dithiopyr )、 式I化合物+達有龍(diuron )、式I化合物+ DNOC、式I ◎ 化合物+ 3,4-DP、式I化合物+ DSMA、式I化合物+ EBEP、 式I化合物+草多索(endothal)、式I化合物+ EPTC、式 I化合物+抑死夫(esprocarb )、式I化合物+伊赛氟拉林 (ethalfluralin )、式 I 化合物 +胺苯項隆 (ethametsulfuron )、式I化合物+胺苯項隆-曱基、式I 化合物+益收生長素(ethephon)、式I化合物+益覆滅 (ethofumesate )、式 I 化合物 + 氣氟苯謎(ethoxyfen )、 66 201014819 • 式I化合物+亞速隆(ethoxysulfuron)、式I化合物+伊 托班尚尼德(etobenzanid )、式 I化合物+芬殺草 (fenoxaprop ) -P、式I化合物+芬殺草-P-乙基、式I化合 物+四β坐草胺(fentrazamide )、式I化合物+硫酸亞鐵、 式I化合物+氟燕靈(flamprop ) -M、式I化合物+伏速隆 (flazasulfuron)、式 I 化合物 + 麥喜為(florasulam)、式 I化合物+伏寄普(fluazifop)、式I化合物+伏寄普-丁基、 式I化合物+伏寄普-P、式I化合物+伏寄普-P-丁基、式I ❹ 化合物+異丙α比草醋(fluazolate)、式I化合物+氣酮確 隆(flucarbazone )、式I化合物+氟酮績隆-納、式I化合 物+氣咬乙續隆(Hucetosulfuron)、式I化合物+氟消草 (fluchloralin)、式 I 化合物 + 氟嗟草胺(flufenacet)、 式I化合物+氟達11秦草酯(flufenpyr )、式I化合物+氟建 唤草酯-乙基、式I化合物+氟節胺(flumetralin )、式I化 合物+氟滅索侖(flumetsulam)、式I化合物+氟米克拉 (flumiclorac )、式I化合物+氟米克拉-戊基、式I化合物 參 +氟米沙立(flumioxazin )、式I化合物+氟米羅必 (flumipropin)、式 I 化合物 + 伏草隆(fluometuron)、式 I化合物+氟羅格賴可芬(fiuoroglycofen)、式I化合物+ 氟羅格賴可芬-乙基、式I化合物+氟杉普(fluoxaprop )、 式I化合物+弗拉頗沙(flupoxam )、式I化合物+氟普帕 希耳 (flupropacil )、式 I化合物+氟普洛奈特 (fluproanate )、式 I 化合物 + 氟咬,績隆(flupyrsulfuron )、 式I化合物+氟啶嘧磺隆-甲基-鈉、式I化合物+芴丁酯 67 201014819 (flurenol)、式I化合物+氟立得酮(fiurid〇ne)、式i 化合物+氟氣得酮(flurochloridone )、式I化合物+氟氣 比(fluroxypyr)、式 I 化合物 + 呋草酮(fiurtain〇ne )、式 I化合物+氟噻乙草酯(fluthiacet)、式I化合物+氟噻乙 草酯-甲基、式I化合物+福美沙芬(fomesafen)、式I化 合物+醯胺績隆(foramsulfuron)、式I化合物+福殺胺 (fosamine)、式 I 化合物 + 固殺草(giuf0Sinate)、式 I 化合物+固殺草-敍、式I化合物+嘉鱗塞(glyphosate )、 式I化合物+鹵殺福隆(halosulfuron)、式I化合物+鹵 殺福隆-甲基、式I化合物+鹵斯弗(haloxyfop)、式I化 合物+鹵斯弗-P、式I化合物+ HC-252、式I化合物+環己 基二曱胺基甲基三牌二嗣(hexazinone )、式I化合物+依 馬扎沙苯(imazamethabenz )、式I化合物+依馬扎沙苯-曱基、式I化合物+甲氧咪草煙(imazamox )、式I化合物 +曱咪唑煙酸(imazapic )、式I化合物+依滅草 (imazapyr )、式I化合物+嗎紮奎(imazaquin )、式I化 合物+嗎茲紮比(imazethapyr )、式I化合物+嗎殺福隆 (imazosulfuron )、式 I化合物 + 茚草嗣(indanofan)、式 I化合物+碘基甲烷、式I化合物+碘甲磺隆 (iodosulfuron)、式I化合物+峨曱續隆-甲基-鈉、式I化 合物+碘苯亞硝酸鹽(ioxynil )、式I化合物+異丙土隆 (isoproturon)、式I化合物+依索隆(isouron )、式I化 合物+依索苯(isoxaben )、式I化合物+異咢氣托 (isoxachlortole )、式 I 化合物 + 異夸氟草(isoxaflutole )、 201014819 式I化合物+依索比立福(isoxapyrifop )、式I化合物+ 卡靈草(karbutilate )、式I化合物+累托芬(lactofen )、 式I化合物+環草定(lenacil )、式I化合物+利倫 (linuron)、式I化合物+ MAA、式I化合物+ MAMA、式 I化合物+ MCPA、式I化合物+ MCPA-硫乙基、式I化合 物+ MCPB、式I化合物+甲氣丙酸(mecoprop )、式I化 合物+甲氣丙酸-P、式I化合物+美芬司特(mefenacet)、 式I化合物+氟草磺(mefluidid)、式I化合物+磺胺磺隆 ❹ (mesosulfuron )、式I化合物+績胺續隆-甲基、式I化合
物+甲基續草酮(mesotrione )、式I化合物+米塔姆 (metam)、式I化合物+咢唆醯草胺(metamifop )、式I 化合物+滅得群(metamitron)、式I化合物+美他佐克羅 (metazachlor )、式 I 化合物+ 甲基苯嘆隆 (methabenzthiazuron )、式 I 化合物 + 滅草0坐(methazole )、 式 I化合物+甲基胂酸、式I化合物+甲基代隆 (methyldymron )、式I化合物+異硫代氰酸曱酯、式I化 〇 合物+美他笨隆(metabenzuron)、式I化合物+秀谷隆 (metobromuron )、式 I 化合物 + 美托克羅(metolachlor )、 式I化合物+ S-美托克羅、式I化合物+美托沙泣 (metosulam)、式I化合物+美托斯隆(metoxuron)、式 I化合物+赛克津(metribuzin )、式I化合物+美殺福隆 (metsulfuron)、式I化合物+美殺福隆-甲基、式I化合 物+ MK-616、式I化合物+莫立那特(molinate )、式I化 合物+莫那立得(monalide )、式I化合物+ MSMA、式I 69 201014819 化合物+那普苯胺(naproanilide)、式I化合物+那普醯 胺(napropamide)、式I化合物+抑草生(naptalam)、式 I化合物+ NDA-402989、式I化合物+草不隆(neburon )、 式I化合物+尼可殺福隆(nicosulfuron )、式I化合物+ 尼比拉西芬(nipyraciophen)、式I化合物+正-甲基嘉填 塞、式I化合物+壬酸、式I化合物+達草滅(norflurazon )、 式I化合物+油酸(脂肪酸)、式I化合物+奥貝卡 (orbencarb )、式 I 化合物 + 歐索確目洛(othosulfamuron )、 式I化合物+黃草消(oryzalin )、式I化合物+奥沙地奇 (oxadiargyl)、式 I 化合物 + 惡草靈(oxadiazon)、式 I 化合物+環氧嘧績隆(oxasulfuron)、式I化合物+咢嗪草 酮(oxaziclomefone )、式 I 化合物 + 奥 I芬(oxyfluorfen )、 式I化合物+巴拉刈(paraquat)、式I化合物+巴拉刈二 氣化物、式I化合物+克草敵(pebulate )、式I化合物+ 培那西林(pendimethalin )、式 I化合物+確醯膝 (penoxulam)、式I化合物+五氣盼、式I化合物+甲氣 草胺(pentanochlor )、式 I化合物+環戊咢草酮 (pentoxazone)、式 I化合物 + 烯草胺(pethoxamid)、式 I化合物+石油、式I化合物+甜菜寧(phenmedipham )、 式I化合物+甜菜寧_乙基、式I化合物+毒赛定 (picloram)、式 I 化合物+ β比氟醜草胺(picolinafen)、 式I化合物+ °比諾山登(pinoxaden )、式I化合物+派羅福 (piperophos )、式I化合物+亞胂酸斜、式I化合物+疊 氮化鉀、式I化合物+普立拉克(pretilachlor)、式I化合 201014819 物+撲滅續曱酯(primisulfuron )、式I化合物+撲滅績甲 酯-曱基、式I化合物+普魯二胺(prodiamine )、式I化合 物+普氟吐(profluazol )、式 I化合物+環苯草嗣 (profoxydim )、式 I 化合物 + 調環酸(prohexadione ) 約、 式I化合物+撲滅通(prometon)、式I化合物+撲草淨 (prometryn)、式 I 化合物 + 毒草安(propachlor)、式 I 化合物+敵稗(propanil )、式 I化合物+西帕奎 (propaquizafop )、式 I 化合物 + 撲滅津(propazine )、式 ❿ I化合物+苯胺靈(propham)、式I化合物+普羅比索克 (propisochlor )、式 I 化合物 + 丙苯績隆 (propoxycarbazone )、式I化合物+丙苯績隆-納、式I化 合物+氣曱丙炔基苯甲醯胺(propyzamide)、式I化合物 +撲沙福卡(prosulfocarb )、式I化合物+撲沙殺福隆 (prosulfuron )、式 I 化合物 + 雙唆草腈(pyraclonil )、式 I化合物+ °比草謎(pyraflufen )、式I化合物+ "比草謎-乙 基、式I化合物+ °比拉蘇福托(pyrasulfotole ) 、_式I化合 Ο 物+ π比唑林特(pyrazolinate )、式I化合物+必拉若殺福 隆-乙基(pyrazosulfuron ) '式I化合物+必拉若殺福隆-乙基、式I化合物+比拉若西芬(pyrazoxyfen )、式I化合 物+峨咬將草謎(pyribenzoxim)、式I化合物+稗草畏 (pyributicarb)、式 I化合物+ »比達夫醇(pyridafol)、式 I化合物+ "比達特(pyridate )、式I化合物+環酯草醚 (pyriftalid )、式 I化合物+ 〇比嘴多巴克(pyrimidobac )、 式I化合物+吡嘧多巴克-甲基、式I化合物+吡嘧蘇發 71 201014819 (pyrimisulfan )、式 I 化合物 + 比立塞巴克(pyrithiobac )、 式I化合物+比立塞巴克-鈉、式I化合物+吡洛山蘇風 (pyroxasulfone ) ( KIH-485 )、式 I 化合物 + °比洛殊蘭 (pyroxulam)、式I化合物+昆多拉克(quindorac )、式 I化合物+昆美拉克(quinmerac )、式I化合物+滅藻 (quinoclamine )、式 I化合物 + 奎拉弗(quizalofop )、式 I化合物+奎拉弗-P、式I化合物+力殺福隆(rimsulfuron )、 式I化合物+稀禾定(sethoxydim)、式I化合物+環草隆 (siduron)、式I化合物+西瑪三拼(simazine )、式I化 ❹ 合物+西草淨(simetryn )、式I化合物+ SMA、式I化合 物+亞胂酸鈉、式I化合物+疊氮化鈉、式I化合物+氣酸 納、式I化合物+項草酮(sulcotrione )、式I化合物+沙 芬曲諾(sulfentrazon )、式 I化合物+殺福美隆 (sulfometuron )、式I化合物+殺福美隆-甲基 '式I化合 物+沙弗司特(sulfosate )、式I化合物+續醯續隆 (sulfosulfuron )、式I化合物+硫酸、式I化合物+焦油、 式I化合物+2,3,6-TBA、式I化合物+ TCA、式I化合物+ 〇 TCA-納、式I化合物+替布他(tebutam)、式I化合物+ 替布塞隆(tebuthiuron )、式 I化合物+替咬退酮 (tefuryltrione )、式 I化合物 + 提波退嗣(tembotrione )、 式I化合物+得殺草(tepraloxydim)、式I化合物+特草 定(terbacil)、式I化合物+甲氧去草淨(terbumeton )、 式I化合物+特丁津(terbuthylazine )、式I化合物+去草 淨(terbutryn )、式 I 化合物 + 西尼克羅(thenylchlor )、 72 201014819 式I化合物+雀殺福隆(thiazafluron )、式I化合物+喧諾 比(thiazopyr )、式 I 化合物 + 逢吩殺福隆(thifensulfuron )、 式I化合物+售卡倍容(thiencarbazone )、式I化合物+ 嗟吩殺福隆-甲基、式I化合物+嗟歐苯卡(thiobencarb )、 式I化合物+替歐卡巴力(tiocarbazil)、式I化合物+托 普米容(topramezone )、式 I 化合物+曲考昔地 (tralkoxydim)、式 I 化合物 + 野麥畏(triallate)、式 I 化合物+三阿蘇殺福隆(triasulfuron )、式I化合物+三牌 e 氟草胺(triaziflam )、式I化合物+三苯那隆(tribenuron )、 式I化合物+三苯那隆-甲基、式I化合物+殺草畏 (tricamba)、式I化合物+定草醋(triclopyr)、式I化 合物+草達津(trietazine)、式I化合物+三氟氧殺福隆 (trifloxysulfuron)、式I化合物+三氟氧殺福隆-鈉、式I 化合物+氟樂靈(trifluralin )、式I化合物+三氟殺福隆 (triflusulfuron)、式I化合物+三氟殺福隆·甲基、式I 化合物+三經基三啡、式I化合物+抗倒醋(trinexapac )-❹ 乙基、式I化合物+三氟甲確隆(tritosulfuron)、式I化 合物+ [3-[2-氣基-4-氟基-5-(1-甲基-6-三氟曱基-2,4-二酮 -1,2,3,4-四氫嘧啶-3-基)苯氧基]-2-°比啶氧基]乙酸乙酯 (CAS RN 353292-31-6)、式 I化合物 +4-羥基-3-[[2-[(2- 甲氧基乙氧基)甲基]-6-(三氟曱基)-3-"比啶基]羰基]雙環 [3.2.1]辛-3-烯-2-酮(CAS RN 372010-68-5 )以及式 I 化合 物+ 4-羥基-3-[[2-(3-曱氧基丙基)_6-(二氟曱基)-3-吼啶基] 幾基]雙環[3.2.1]辛-3-烯-2-酮。 73 201014819 式i化合物的混合伙伴也可具有酯類或鹽類形式,例如 例在2000年的第12版殺蟲劑手冊(The Pesticide Manual ) (BCPC)中所說明者。 根據本發明的式I化合物也可與安全劑組合使用。較佳 地,在這些混合物中,式I化合物為那些在下列表1至102 中所列之化合物中之一。特別考慮下列的具有安全劑的混 合物: 式(I)化合物 + 解毒喧(cloquintocet-methyl)、式(I)化 合物+解毒喹酸及其酯、式(I)化合物+解草唑 (fenchlorazole-ethyl )、式(I)化合物+解草0坐酸及其醋、 式(I)化合物+ °比0坐解草酯(mefenpyr-diethyl)、式(I)化合 物+ D比嗤解草醋二酸、式(I)化合物+雙苯°惡°坐酸 (isoxadifen-ethyl )、式(I)化合物+雙苯°惡°坐酸 (isoxadifen-acid )、式(I)化合物 + 解草 °惡嗤(furilazole )、 式(I)化合物+解草噁唑R異構物、式(I)化合物+解草嗪 (benoxacor)、式(I)化合物 + 二氣丙稀胺(dichlormid)、 式(I)化合物+ AD-67、式(I)化合物+解草腈(oxabetrinil )、 式(I)化合物+解草胺腈(cyometrinil )、式(I)化合物+解 草胺腈Z-異構物、式(I)化合物+解草啶(fenclorim )、式 ⑴化合物+賽普蘇法麥得(cyprosulfamide)、式(I)化合物 +萘酸酐、式(I)化合物+解草安(flurazole )、式(I)化合物 + N-(2-曱氧基苯甲醯基)-4-[(曱胺基羰基)胺基]苯磺醯胺、 式⑴化合物+ CL 304,415、式⑴化合物+二賽可羅諾 (dicyclonon )、式(I)化合物 + 氟草肪(fluxofenim )、式 74 201014819 • (I)化合物+ DKA-24、式(I)化合物+R-29148及式(I)化合物 + PPG-1292。安全化效果也可於式(I)化合物+汰草龍 (dymTon )、式(I)化合物+ MCPA、式(I)化合物+米可迫普 (mecoprop )及式(I)化合物+米可迫普-P之混合物而觀察 到。 上述安全劑及除草劑被述敘在,例如,英國作物保護 委員會(British Crop Protection Council)於 2000 年的第 12版殺蟲劑手冊中。R-29148係由例如P. B. Goldsbrough ❹ 等人於 Plant Physiology,(2002),Vol. 130,pp. 1497-1505 與 其中的參考文獻所敘述。PPG-1292係從WO09211761已知 及N-(2-甲氧基苯曱醯基)-4-[(甲胺基羰基)胺基]苯磺醯胺 係從EP365484已知。 解草 °秦(benoxacor )、解毒啥(cloquintocet-mexyl) ’、 赛普蘇法麥得 (cyprosulfamide ) 、°比嗤解草醋 (mefenpyr-diethyl)以及N-(2-甲氧基苯甲醯基)-4-[(甲基 胺基羰基)胺基]苯磺醯胺為特佳,其中以解毒喹最有價值。 φ 安全劑相對於除草劑之施用率大半地視施用模態而 定。在田間處理之情形中,施用通常從0.001至5.0公斤安 全劑/公頃’較佳從〇·〇〇1至0.5公斤安全劑/公頃,和通 常從0.001至2公斤除草劑/公頃,但較佳地從0.005至1 公斤/公頃。 根據本發明之除草組合物適合於所有農業中習知的施 用方法,如例如,萌芽前施用、萌芽後施用和浸種。視所 欲的用途而定,安全劑可用於預處理作物植物之種子物質 75 201014819 (浸種子或苗木)或在播種之前或之後引入土壤内,接著 施用(未安全化)之式(I)化合物,視需要與共-除草劑合併。 然而,也可在植物的萌芽之前或之後單獨施用或與除草劑 一起施用。用安全劑處理植物或種子物質可因此原則上與 除草劑之施用時間獨立地發生。植物藉由同時施用除草劑 和安全劑之處理(例如於桶混劑(tank mixture )之形式) 通常為較佳。安全劑相對於除草劑之施用率大半地視施用 模式而定。在田間處理的情況中,施用通常從〇.〇〇丨至5.〇 公斤的安全劑/公頃,較佳從0.001至0.5公斤的安全劑/ 公頃。在浸種之情形中,施用通常從0.001至1〇克之安全 劑/公斤之種子,較佳從0.05至2克之安全劑/公斤之種 子。當以液體形式施用安全劑,且在播種之前不久,浸泡 種子時,使用包含從1至10000 ppm,較佳從100至1〇〇〇 ppm 之濃度的活性成分之安全劑溶液是有利的。 較佳將其他除草劑與上述一種安全劑一起施用。 下列的實施例進一步說明本發明,但不是限制本發明。 製備實施例: 那些熟習所屬技術領域者將理解下述的某些化合物為 /3-酮稀類,並照其原樣子可以單一互變異構物或以酮基· 烯醇與二酮互變異構物之混合物存在,例如例由j March 於 John Wiley and Sons 的第 3 版 Advanced 〇rganic
Chemistry所述。在表T1中所示之化合物係以任意的單一 烯醇互變異構物所描繪’但是應做出該說明涵蓋二酮型式 及可經由互變異構現象引起的任何可能的烯醇二者的推 76 201014819 斷。再者,為了簡化起見,表T1及表ρι 繪成單一互變異構物,但是除非被特定為些化合物被 物’這些結構應該被解讀為代表 單一互變異構 細的實驗章節之内,二綱互變昱搂札於 成合物。在詳 笑兵構物係以命 擇,即使主要的互變異構物為稀醇 為目的而選 在質子NMR中觀察到—個以上之互變異 示數據為互變異構物混合物。 '構物中’所顯 實施例1 Φ 2,2-二甲基·丙酸3-側氧基(四氫·吡 基)-2-(2,4,6-三甲。基-苯基).環戊烯醋之製傷比K基甲
步驟1 : 2-(2,4,6-三甲基苯基)_3·甲氧基-環戊烯蜩之製備
對2-溴-3-甲氧基-環戊-2-烯酮(6.75克,35.3毫莫耳), 2,4,6-三甲基苯基硼酸(6.99克,42.6毫莫耳)及剛研磨之麟 酸鉀(15克’ 70.6毫莫耳)於脫氣體甲苯(180毫升)中之懸浮 液加入Pd(OAc)2(159毫克,0_71毫莫耳)及S-Phos(579毫 克,1.41毫莫耳),且反應在氮氣下及攪拌下被加熱至90°C 77 201014819 達4小時。反應混合物被乙酸乙酯(150毫升)及水(15〇毫升) 之間分層’且有機層被移除。將石夕膠加入有機層,在減壓 下蒸發溶劑’且殘留物於石夕膠上經快速層析術純化而得到 2-(2,4,6-三甲基苯基)-3-甲氧基-環戊-2-稀酮(6.2克)。 步驟2 : 5-[經基-(四氫比味-4-基)-甲基]·3_甲氧基]_2(2,4,6-三 曱基-苯基)-環戊-2-烯酮之製備
Ν-乙基-Ν,Ν-二異丙基胺(527微升,3.76毫莫耳)於四氫 吱锋(5毫升)中之溶液於氮氣下於_78<t被滴加2 5Μ 丁鋰於 己烷中之溶液(1.32毫升,3_3毫莫耳),以及讓反應於_78。〇 攪拌20分鐘。然後,在氮氣之下於1〇分鐘將此淺黃色溶 液滴加入2-(2,4,6-三甲基苯基)-3 -甲氧基-環戊·2_烯酮(691 毫升’ 3毫莫耳)於四氫呋喃(5毫升)令之溶液(被預熱至·78 Q °C)。讓所得溶液於_78〇C攪拌4〇分鐘。然後一次加入四氫 吡喃-4-甲醛(377毫克,3 _3毫莫耳)於四氫呋喃(1毫升)中之 溶液’ όο分鐘内被回溫至室溫之前,反應混合物於於_78它 被攪拌30分鐘。藉添加飽和氣化銨水溶液毫升)使反應 驟冷且以乙酸乙酯(2x50毫升)進行萃取。混合的有機物經 快速層析術純化而得到5•[羥基_(四氫·吡喃_4基)_曱基]_3_ 曱氧基]-2(2,4,6-三甲基-苯基)·環戊_2_烯酮(648毫克)。 78 201014819 * 步驟3 : 4-[1-(四氫〇比味·4·基)-亞-(E)-甲基]-2-(2,4,6-三甲基 苯基)-環戊烷-1,3-二酮之製備
對5-[羥基-(四氫比喃-4-基)-甲基]-3-曱氧基]_2(2,4,6_ φ 三甲基-苯基)-環戊-2-烯酮(408毫克’ 1.18毫莫耳)於丙酮(2 毫升)中之溶液加入2N氫氣酸(2毫升)且所得溶液被微波加 熱90分鐘至130°C。反應混合物被2N氫氣酸(25毫升)稀 釋,且經乙酸乙酯(2x25毫升)萃取。經混合之有機物被鹽 水(25毫升)沖洗,經硫酸鎮乾燥,過渡及在真空下濃縮而 得到4-[1-(四氫- η比喊-4-基)-亞- (E) -甲基]-2-(2,4,6-三曱基-苯基)-環戊烷-l,3-二酮(302毫克)。 步驟4 : Q 4-(四氫·η比喃-4-基甲基)-2(2,4,6-三甲基-苯基)_環戊烧 -1,3-二酮之製備
對4_[1·(四氫-ο比喃-4-基)-亞-(E)-曱基]-2-(2,4,6-三曱基 -苯基)-環戊烷-1,3•二酮(270毫克,0.86毫莫耳)於乙醇(1〇 毫升)中之溶液加入10%碳上鈀(27毫克),且所得溶液在氫 79 201014819 氣(3巴)及室溫下攪拌5小時。然後,反應混合物經矽藻土 墊過濾’其經甲醇沖洗,且濾液在真空下經濃縮而得到心(四 氫-吡喃-4-基曱基)_2(2,4 6_三甲基_笨基)環戊烷_13二酮 (258毫克)。 步驟5 : 2,2-二曱基丙酸3_側氧基_4_(四氫吡喃_4甲 基)-2-(2,4,6-三甲基_苯基)_環戊_1_稀酯之製備
對4-(四氫-吡喃-4-基甲基)·2(2,4,6-三甲基-苯基)·環戊 烷-1,3-二酮(100毫克,0.25毫莫耳)於二氣甲烷(5毫升)及 三乙胺(140微升,1毫莫耳)中之溶液於室溫下被加入三甲 基乙酿基氣化物(91微升’ 1毫莫耳)。反應混合物於室溫下 經攪拌隔夜。將矽膠加入粗反應混合物,在減壓下蒸發溶 劑,且殘留物於矽膠上經快速層析術純純化而得到2,2-二甲 基-丙酸3-側氧基-4_(四氫-吡喃-4-甲基)_2J2,4,6-三甲基_笨 基)-環戊-1-烯酯(102毫克)。 實施例2 : 2-(3,5-二甲基聯苯-4-基)-4-(四氫咳喃-3-基甲基)環戊 烷-1,3-二酮之製備 80 201014819
2 (3’5 —甲基聯苯_4_基)_3·甲氧基環戊_2稀嗣之製備
對2-(4->臭_2,6_二甲基笨基氧基環戊-2稀嗣 毫莫耳)、氟化絶(1.5克,9.87毫莫耳)、苯基蝴酸 4·1毫莫耳)及以,1’·雙(二苯基膦基)苐]二氣-把(II) •44 0.54毫莫耳)之混合物加人脫氣之二甲氧基乙烧(1〇 毫升)且所件懸浮液於氮氮下被授拌Μ分鐘錢被加熱至 〇 C ^ 4小時。在冷卻至室溫之後,反應混合物被…水性 氣化虱酸化。水相進一步經乙酸乙酯(3χΐ〇〇毫升)萃取以 及然後所有有機部分經混合,經無水硫酸鈉乾燥以及在真 空中經濃縮。所得材料於矽膠上經管柱層析術純化而提供 為白色固體之2-(3,5-二甲基聯苯_4_基)_3_甲氧基環戊_2_烯 酮(0.7克)。 步驟2 : 2-(3,5-二甲基聯苯-4-基)-5-[經基·(四氫〇夫喃基)甲 基]-3-甲氧基-環戊-2-烯酮之製備 81 201014819
在-75°C及在氮氣下對2-(3,5·二甲基聯苯_4•基)_3_甲氧 基環戊-2·烯酮(0.6克’ 2.05毫莫耳)於四氣咬喃(12毫升)中 之溶液加入雙(三甲基矽烷基)醯胺鋰於四氫呋喃(25毫 升’ 2·5毫莫耳)中之1莫耳溶液。所得到的溶液於-75。(:攪 拌40分鐘,且於20分鐘對此混合物加入3四氫呋喃甲醛 (0.42克,4.1毫莫耳)在四氫呋喃中之溶液。所得溶液於_75 φ °C攪拌2小時。移走冷卻浴且讓混合物達到室溫,然後攪 拌2小時。反應混合物經冰冷水(1〇〇毫升)驟冷且經乙酸乙 酯(3x75毫升)萃取,經無水硫酸鈉乾燥,過濾且濾液於真 空下經濃縮而得到殘留物(1>1克),其本身供下一道步驟使 用0 步驟3 : 2-(3,5 - 一曱基聯苯基)_4_[ι_(四氫呋喃_3•基)亞曱 基]-環戊统-1,3-二酮之製備 ❹
2-(3,5-二曱基聯苯_4-基)_5_[經基_(四氫吱喃_3_基)甲 基]-3-甲氧基-環戊-2-烯酮(1.1克,2.8毫莫耳)、丙嗣(21毫 升)及2N氫氣酸(10毫升)之混合物在n(rc微波下經加熱 40分鐘。在真空下蒸發有機溶劑’經水(1〇〇毫升)稀釋以及 82 201014819 經混合的有機萃取物經混 經乙酸乙酯(3xl〇〇毫升)萃取 合,經水及鹽水沖洗,經無太访Α ^ 热水硫酸鈉乾燥,過濾且濾液在 真空下經濃縮。殘留物於矽膠上姐垃h a i 修上經管柱層析術純化而得到 2_(3,5_二甲基聯苯-4-基丄上 u (四氫呋喃-3-基)亞曱基]-環 戊烷-1,3-二酮(0.29 克)。 步驟4 : 2-(3,5-二曱基聯苯-4-基、_4 fnn & i ^ I) 4-(四氫呋喃-3_基甲基)_環戊 烷-1,3-二酮之製備
Ο 對2-(3,5·二曱基聯苯(四氫吱喃_3_基)亞曱 基]-環錢-U3-二酮(0.29克,〇·8毫莫耳)於甲醇〇〇毫升) 中之溶液加入10%碳上把(0.06克),接著在1巴氮大氣之下 攪拌8小時。然後反應混合物經矽藻土過濾及經濃縮而得 Q 到粗產物,其經快速層析術(己烷/乙酸乙酯)純化而提供 2-(3,5-一甲基聯苯_4_基)_4_(四氫呋喃基甲基)_環戊烷 -1’3 -一 綱(〇·ΐ2 克)。 實施例3 : 2-(4-氟_2,6_二曱基苯基)_4_(四氫呋喃_4基甲基)環戊 燒-1,3-二_之製備 83 201014819
步驟1 : (4-氟-2,6-二甲基苯基)呋喃基甲醇
於-75°C及氮氣大氣下 η -氟·2-碘·1,3-二曱苯(1 克,44毫莫耳)於四氫呋喃(11〇毫 丌)甲之溶液加入1.6莫3 正丁基㈣己即3毫升,52毫莫耳)。所得溶液於-75U 拌60分鐘’且於20分鐘對此混合物加入糠链(63克,Μ
毫莫耳)於四氫吱喃(2〇毫升)中之溶液。所得溶液於孩相 授拌2小時。移走冷卻浴且讓混合物達到室溫,且然後利 拌5小時。以冰冷水(1000毫升)使反應混合物驟冷,且趟 乙酸乙酯萃取(3x250毫升),經無水硫酸鈉乾燥,過濾且级 液在真空下經濃縮而得到殘留物,其經快速層析術(己烷 乙酸乙酯)純化而提供(4-氟-2,6·二甲基苯基)呋喃_2•基甲g (6 克)。 步驟2 : 5-(4-氟-2,6-二曱基苯基)-4-羥基環戊-2-烯酮之製備 84 201014819
(4-氟-2,6-二甲基苯基)呋喃-2-基曱醇(6克,27毫莫 耳)、丙鋼(150毫升)、水(24毫升)及正磷酸(0.6毫升)之混 合物於120C在微波條件下被加熱50分鐘。在真空下蒸發 有機溶劑’經水(150毫升)稀釋且經乙酸乙酯萃取(3χ1〇〇毫 升)°經混合的有機萃取物經混合,經水及鹽水沖洗,以無 水硫酸鈉乾燥,過濾且濾液於真空下經濃縮。殘留物於矽 膠上經管柱層析術純化而得到5_(4_氟_2,6_二甲基苯基)_4_ 幾基環戊-2-烯酮(3克)。 步驟3 : 2-(4-氟-2,6-二甲基苯基)環戊_4•烯-丨,3二酮之製備
於〇°C對 ' 5-(4-氟-2,6_二Τ基苯基)-4-羥基環戊-2-烯酮 rx 古,13 6 铽甘•人——
85 201014819 步驟4 : 2 (4氟-2,6-二甲基笨基)·環戊烷_13二酮之製備
於 25-30 C _ 2-(4·氟_2,6-二曱基苯基)環戊·4_稀.i,3 •二 嗣(9克13·3毫莫耳)於乙酸(116毫升)中之溶液加入鋅粉 (6克’ 91.7毫莫耳)。所得溶液於25-3(TC攪拌16小時。然 後’反應混合物經矽藻土過濾且經濃縮而得到粗產物(29 克)’其供下一道步驟使用。 步驟5 : (氟2,6 —甲基笨基)-3 -曱氧基-環戊·2_烯酮之製備 對2-(4-氟-2,6-二甲基苯基)_環戊烷二酮(29克 13.3毫莫耳)於四氫呋喃(20毫升)中之溶液加入碳酸鉀(22 克,159毫莫耳)及碘甲烷(22.6克,159毫莫耳)。所得混合 物於25-3G°C經攪# 16小時。有機層經蒸發,反應混合物 經水(150毫升)驟冷且經乙酸乙酯萃取(3χ1〇〇毫升)。經混合 的有機萃取物經混合,經水及鹽水沖洗,以無水硫酸鈉乾 燥’過遽且溏液於真空下經濃縮。殘留物於珍膠上經管柱 層析術純化而得到2-(4-氟-2,6-二甲基苯基;)_3_甲氧基_環戊 -2-烯酮(2克)。 201014819 步驟6 : _2-烯鲷之製備 2-(4- ^ -2,6-一甲基苯基)-3 -甲氧基_環戊
在-75°C及在氮氣下對2-(4-氟-2,6-二甲基苯基)_3
基環戊·2-稀酮(0·5克,2<1 *莫耳)於四氫吱喃(1〇毫升甲)$ 之溶液加入雙(三甲基矽烷基)醯胺鋰於四氫吱味(2 7毫 升,2.5毫莫耳)中之1莫耳溶液。所得到的溶液於75它攪 拌40分鐘’且於20分鐘對此混合物加入3_四氫吱味甲醒 (0.5克’ 4·38毫莫耳)在四氫呋喃中之溶液。所得溶液於_75 C檟:拌2小時。移走冷卻浴且讓混合物達到室溫,然後授 拌2小時。反應混合物經冰冷水(1 〇〇毫升)驟冷且經乙酸乙 酯(3χ75毫升)萃取,經無水硫酸納乾燥,過瀘且滤液於真 空下經濃縮而得到殘留物(0.7克),其本身供下一道步驟使 用。 步驟7 : 2-(4-氟-2,6-二甲基苯基)-4-[四氫〇比〇南_4_基]_亞甲基]-環戊烧-1,3 -二酮之製備
2-(4-氟-2,6-二甲基苯基)-3 -甲氧基-5-[1-四氫〇夫鳴-4- 87 201014819 基]-乙基h環戊-2-烯酮(0.7克,2毫莫耳)、丙酮(i〇毫升) 及2N氫氣酸(10毫升)之混合物在130°c微波下經加熱4〇 分鐘。在真空下蒸發有機溶劑’經水(丨00毫升)稀釋以及經 乙酸乙醋(3 X 7 5毫升)萃取。經混合的有機萃取物經混合, 經水及鹽水沖洗’經無水硫酸鈉乾燥,過濾且渡液在真空 下經濃縮。殘留物於矽膠上經管柱層析術純化而得到2_(4_ 氟-2,6·二甲基苯基)-4-[四氫吡喃-4·基]-亞甲基]-環戊烧 1,3_二酮(0.23 克)。 步驟8 : 2-(4-氟-2,6-二甲基苯基)-4-[四氫"比喃-4-基甲基]-環戊 烷-1,3-二酮之製備
對2-(4-氟-2,6-二甲基苯基)-4-[四氫吡喃-4-基]-亞甲 基]-環戊烷-1,3-二酮(0.14克,0.44毫莫耳)於曱醇(3毫升) 中之溶液加入10%碳上鈀(1.5毫克),接著在1巴氫大氣之 © 下攪拌8小時。然後反應混合物經矽藻土過濾及經濃縮而 得到粗產物,其經快速層析術(己烷/乙酸乙酯)純化而提供 2-(4-氟-2,6-二甲基苯基)-4-[四氫°比喃-4-基甲基]-環戊烷 -1,3-二鲖(0.13 克)。 實施例3 : 2-(4-溴-2,6-二甲基苯基)-4-(四氫吡喃-4-基甲基)環戊 烷-1,3-二嗣之製備 88 201014819 .0 .
Br 在20巴氫氣大氣之下使用10%鉑碳及在H-Cube條件 下使2-(4_溴-2,6_二甲基苯基)_4_[1_(四氫吡喃-4_基)_亞甲 基]-環戊烷-1,3-二酮(0.1克,0·26毫莫耳)於甲醇(1〇〇毫升) φ 中之溶液進行 氫化。然後,使反應混合物濃縮而得到粗產 物’其經快速層析術(己烧/乙酸乙酯)純化而提供2-(4-漠 _2,6_二甲基苯基)-4-(四氫吡喃-4-基甲基)環戊烷4,3_二酮 (〇.〇9 克) 實施例4 : 2_(2,6 -二曱基苯基)-4-(四氫"比喃-4-基甲基)環戊燒 _1,3-二酿I之製備
對2-(4-溴-2,6-二甲基苯基)-4-[1-(四氫0比喃_4_基)_亞甲 基]·環戊烷-1,3-二酮(〇.3克,0.8毫莫耳)於曱醇(5毫升)中 之溶液加入10%碳上鈀(0.06克),接著在丨巴氫大氣之下攪 拌8小時。然後反應混合物經矽藻土過濾及經濃縮而得到 粗產物,其經快速層析術(己烷/乙酸乙酯)純化而提供 2·(2,6-二曱基苯基)_4_(四氫吡喃_4基甲基)環戊烷n 一 89 201014819 酮(0.12 克)。 實施例5 : (環丙基_2,6-—甲基-笨基)_心(四氫〇比味_4_基甲基)-環戊烷-1,3-二酮之製備
對2-(4-漠-2,6_二曱基苯基)_4 (四氫吡喃_4基甲基)環 戊烷_1,3_二酮(0.1克,〇·2ό毫莫耳)、磷酸鉀(〇·ιι毫克,0.53 毫莫耳)、環丙基硼酸(0.09克,1 〇5毫莫耳)及四(三苯基膦) 鈀(0) (0.06克’ 0 053毫莫耳)、甲苯(2毫升)、二甲氧基乙 烧(〇·5毫升)及水(〇.5毫升)之混合物於130〇C微波條件下被 加熱22分鐘《在真空下蒸發有機溶劑,以水稀釋且經乙酸 乙醋萃取(3x25毫升)。經混合之有機萃取物被混合,經水 及鹽沖洗’經無水硫酸鈉乾燥,過濾且濾液在真空下濃縮。 殘留物於碎膠上經管柱層析術純化,接著在矽膠上經製備 HPLC純化而得到2·(4_環丙基·2,6-二甲基-苯基)_4-(四氫吡 喃-4-基甲基)-環戊烧_ι,3_二酮(0.012克)。 實施例6 : (4-(1-環丙烷羰基-六氫吡啶-4-基甲基)_2_(2,4,6-三甲 基-苯基)-環戊烷-1,3-二酮之製備 201014819
步驟1 : 4-[4-甲氧基-2-側氧基-3-(2,4,6-三甲基-苯基)-亞環戊 -3-烯-(E)-基曱基]-六氫吡啶_1_羧酸三級丁酯之製備
於30分鐘期間在_78。〇及氮氣下對2-(2,4,6-三甲基苯 基)-3 -甲氧基-環戊-2-烯酮(9.05克,39.21毫莫耳)於四氫呋 喃(150毫升)中之溶液滴加二異丙基醯胺(24毫升,43.24毫 莫耳,1.8M於己烷/四氫呋喃/乙基苯中),讓反應在此溫度 下另外攪拌30分鐘。然後一次加入4-甲酿基·六氫吡啶-1-羧酸三級丁酯(10克,3.24毫莫耳),在被容許在6〇分鐘期 間回溫至至室溫之前,使反應保持在°C達30分鐘。然 後,一次加入三級丁氧化鉀(7.28克,64_86毫莫耳),在室 溫下另外攪拌反應2小時。 藉添加飽和氯化銨水溶液(5〇〇毫升)使反應驟冷,以及 經乙酸乙酯萃取(500毫升)。移除有機層,將矽膠加入有機 層,在減壓下蒸發溶劑,殘留物於矽膠上經快速層析術純 化而得到4-[4-甲氧基-2-侧氧基_3_(2 4 6三甲基苯基)亞 環戊-3-烯调-基甲基]-六氫。比咬小綾酸三級丁醋(15 33 克)。 步驟2 : 201014819
4-[4-甲氧基-2-側氧基-3-(2,4,6-三甲基_苯基)_環戊_3 烯甲基]-六氫吡啶-1-羧酸三級丁酯之製備 對4-[4-甲氧基-2-側氧基- 3-(2,4,6-三甲基-苯基)-亞環 戍-3·烤-(E)-基甲基]-六氮比咬_ 1 _竣酸三級丁醋(15 33克, 36.02毫莫耳)於乙醇(150毫升)中之溶液添加1〇%活性炭上 鈀(1.53克),反應在氫(4巴)下經攪拌數小時。反應經矽藻 土塾過遽,在減壓下除去溶劑而得到[4-甲氧基-2-侧氧基 -3-(2,4,6-二甲基-苯基)_環戊_3_烯甲基]_六氫吼啶_1_羧酸三 級丁酯(15.4克)。 步驟3 : 4-[2,4-二側氧基d_(2,4,6_三甲基苯基)環戊基甲基卜 六氫吡錠鹽酸鹽之製備
對4_[4·甲氧基-2·側氧基-3-(2,4,6-三甲基-苯基)-環戊 -3-烯曱基]-六氫吡啶羧酸三級丁酯(15 4克,36毫莫耳) 於丙酮(1〇〇毫升)中之溶液加入2NHC1(1〇〇毫升),反應被 加熱至回流達4小時。在減壓下除去溶劑而得到4_[2,4_二 側氧基-3_(2,4,6-三甲基-苯基)·環戊基曱基]•六氫吡錠鹽酸 鹽(12.58 克)。 92 201014819 步驟4 :
環丙烧缓酸4-(1-環丙烧幾基-六氫β比咬基甲基)_3_ 側乳基- 2- (2,4,6-二甲基-本基)_環戍_1_稀基醋之製備 對4-[2,4-二侧氧基_3-(2,4,6-三甲基-苯基)_環戊基甲 基]-六氫n比鍵鹽酸鹽(175毫克,0.5毫莫耳)於DCM(5毫升) 中之懸浮液加入三乙胺(697微升,5毫莫耳),接著加入環 丙基羰基氣化物(608微升,4.5毫莫耳),且反應在室溫下 經攪拌5小時。將矽膠加入粗反應,在減壓下蒸發溶劑, 且殘留物在矽膠上經快速層析術純化而得到環丙烷幾酸 4-(1-環丙烷羰基-六氫》比啶_4_基甲基)-3-側氧基-2-(2,4 6-= 曱基-苯基)_環戊-1_烯基酯(162毫克)。 步驟5 : 4-(1-環丙烷羰基-六氫吡啶-4-基甲基)_2_(2,4,6-三甲基 -苯基)-環戊烧-1,3-二酮之製備
對4-(1-環丙烷羰基·六氫吡啶_4_基曱基)_3_侧氧基 -2-(2,4,6-三甲基·苯基)_環戊_丨_烯基酯(162毫克,〇 %毫莫 耳)在甲醇中之懸浮液加入碳酸鉀(149毫克,1.08毫莫耳) 以及反應在室溫下經攪拌4小時。在減壓下除去溶劑,且 93 201014819 殘留物經溶於水(2毫升)中。然後加入2N HCl(3毫升),以 及所仔沉殿物被過滤,經己燒沖洗,以及經空氣乾燥而得 到4-(1-環丙烧羰基-六氫吡啶-4-基曱基)_2-(2,4,6-三甲基_ 苯基)-環戊烷-1,3-二酮(72毫克)。 實施例7 : 4_(四氫-吡喃-4-基甲基)-2·(2,4,6-三甲基-苯基)-環戊烷 -1,3-二酮之鈉鹽之製備
在氮氣及室溫下,將0.5Μ甲氧化鈉在甲醇(2毫升,1 毫莫耳)中之溶液加入4-(四氫-吡喃-4-基甲基)-2-(2,4,6-三 甲基-苯基)-環戊烷-1,3-二酮(3 14毫克,1毫莫耳)。反應混 合物於室溫下經攪拌15分鐘。反應混合物於減壓下蒸發而 得到4-(四氫比喃-4-基曱基)-2-(2,4,6-三曱基-苯基)-環戊 烷-1,3-二酮之鈉鹽(336毫克)。 在質子NMR中觀察到一個以上之互變異構物或旋轉構 像異構物中,所顯示數據為異構物及構像異構物之混合物。 除非另外陳明,在環境溫度記錄質子NMR光譜。 化合物藉HPLC-MS之特徵化係使用以下所述三種方法 之一加以分析。
方法A 使用配備Waters Atlantis dC18管柱(管柱長20毫米, 201014819 " 管柱内徑3毫米,粒子尺寸3微米,溫度為40°C )、Waters t 光二極體陣列及 Micromass ZQ2000 之 Waters 2795 HPLC 分析以HPLC-MS特徵化之化合物。根據以下梯度表,分析 係使用三分鐘操作時間進行: 時間(分鐘) 溶劑A(%) 溶劑B(%) 流量(毫升/mn) 0.00 90.0 10.0 2.00 0.25 90.0 10.0 2.00 2.00 10.0 90.0 2.00 2.50 10.0 90.0 2.00 2.60 90.0 10.0 2.00 3.0 90.0 10.0 2.00
溶劑A :含有0.1%HCOOH之H20 溶劑 B :含有 0.1%HCOOH 之 CH3CN
方法B 使用具有配備Waters Atlantis dC 18 IS管柱(管柱長20 毫米,管柱内徑3毫米,粒子尺寸3微米)、Waters2996光 二極體陣列、Waters 2420ELSD 及 Micromass ZQ2000 之 1525微泵HPLC之Waters 2777注射器分析以HPLC-MS特 徵化之化合物。根據以下梯度表,分析係使用三分鐘操作 時間進行: 95 201014819 時間(分鐘) 溶劑A(%) 溶劑B(°/〇) 流量(毫升/mn) 0.00 95.0 5 1.300 2.50 0.00 100 1.300 2.80 0.00 100 1.300 2.90 95.0 5 1.300
溶劑A :含有0.05%TFA之H20 溶劑B :含有0.05%TFA之CH3CN 方法C © 使用具有配備Waters Xterra管柱(管柱長50毫米,管 柱内徑4.6毫米,粒子尺寸3.5微米,溫度40°C)、Waters 光二極體陣列及 Micromass ZQ2000 之 Finnigan Surveyor MSQ Plus以分析HPLC-MS特徵化之化合物。根據以下梯 度表,分析係使用六分鐘操作時間進行: 時間(分鐘) 溶劑A(%) 溶劑B(%) 流量(毫升/mn) 0.00 90.0 10.0 1.30 3.80 0.00 100 1.30 4.80 0.00 100 1.30 5.00 90.0 10.0 1.30 6.00 90.0 10.0 1.30
溶劑A :含有0_05%HCOOH之H20 溶劑 B :含有 0.05%HCOOH 之 CH3CN 96 201014819 化合物 編號 結構 ^nmr (CDC13,除非有另外陳 述),LC/MS或其他的物理數據
T1 δ wwn 1.05-1.10 (m, 6H), 1.^-145 <m, 3H), 1,4S-lS7(m, 1H), 1,62-1.72 im, 3H). 1.90-1.^ (m, 2H)T 2.32-2,39 (m, 8H), S.36-343 (m, 2H). 3,93-3.8© (m, 2H) T2 〇i^X 8 pjwn t.14 (t, 3H}, 1.28-1.43 {m( 3H), 1S8-1J4 imf 3H), 1.85-197 (m, 1H}r 2,50 (qt 2H)4 2.61-3,10 (m, 3 H), 3.30-3,47 {m, 2H), 3,89-4.02 (mt 2H), 7.24 (d, 1H), 7.3&-7.41 (mt 2H>, 7.42 (d, 1H), 7.45-7.49 (m, 2H>. 7M <dd, 1H) T3 6 ppm 1 JO-1.58 (m, 2H), 1.86-1.82 (mt 3H)f 2.09 (b, 6H). 2.27 (s, 3H), 2.32-2.43 (m, 1H), 2.69-2.82 (mt 1H), 2,9&(&, 1H), 3.35-3,40 Cm, 2H), 3,67-3.76 (m, 1H), 3J9-4.11 (mt 2H), 6.90 (s, 2H) T4 5 ppm 129-146 {m. 3H), 1.61-1.76 (m, 3H), 1.86-1.98 {m, 1H)f 2,08 (d, 6H), 2.28 (s, 3H), 2.37 (d (br), 1H}, 2.80-2.95 〇^° (m, 2H), 3.36-3,47 (m, 2H)( 3.92-4.04 <m, 2H}t 6.92 (s, 2H) TS $ ppm 1.4&-1.68 (m. 2H), 2.0S-2.13 (m, 8H), 2.28 (S, 3H), 2,33-2.46 (m, 2H), 2.80-2.S6 (m (br), 2H), 3,38-3.47 (m, 1H), 3J8 (dd. 1H), 3.86-3.92 (m, 1H), 3,95 (dd,1H>, 6.92 {S, 2H) T6 δ ppm 1.46-1.61 (m, 2H), 1,66-1.86 (m, 1H), 193-2,05 (m, 2H), 2,07-2.09 (m, 6H), 2.27 (s, 3H), 2.65-2J3 (m, 6H), 2^91-3.05 (ms 1H), 3.67 (d+ 1H), 6.90 (s, 2H) 97 201014819 了 7 δ upm 1.41-163 (m, 1H>, 1JS-2.02 (m, 4H), 2.05-2J0 (m, m}, 2,12-2.25 (m, 2H), 2.28 (s, 3H), 2,30-2.38 (m, 1H)t 2.83-3,14 (m, 6H), 6.93 (s. 2H) T8 〇DW δ ppm 1.51-1.73 (m. 4H), 2.10 (s, 6H), 2.29 (s, 3H>, 2.40-2.55 (m, 1H), 3,13 (s, 2H), 3.48 (tdt 2H), 3.02-4.06 (m, 2H), 6.01 8.94 (S, 2H) T9 δ ppm 1.67 (m, 2H). 1,98-2,08 (m, 2H), 2.10 (s, 6H), 2J7-2.30 (m, 4H), 2.63-2.83 (m, 4H), 3.09 (fh 2H), 6,00 (d, 1H), 6.94 (s,2H) Τ10 S ppm 2.10 <s, 6H), 2,13-2.25 (m, 5H), 2.29 (s, 3H), 2.44*2.62 (m, tH), 2.99-3.27 (m, m), 6.02 {d, 1H), 6.84 (s, 2H) Τ11 LOMS (方法 A) MH+ = 34S rt* 1.17分鐘 τ« LC4«S(方法 A) ES4: MHT:441 Τ13 LC*MS (方法 A) ES+: MH+ = 402 rt=1.31分鐘 98 201014819
T14 〇i^ LOWS《方法 A 〇 ES": = 313 rt篇1,39分鐘 T15 VO^ LC4yiS (方法 A) ES+: Μβ = 354 rt = 1.27分鐘 T16 LG^S (方法 a) ES’: ΜΗ,·31δ rt=1.34 分鐘 117 o^y LC*MS (方法人)EST: MIT = 200 rt=1,27 分鐘 ns iC"MS(方法 λ) ES·: MlT = 3t>1 rtM,36分鐘 ΤΪ9 b i U>MS (方法 A) ES,: MH,= 299 rt* 1.32分鐘 99 201014819 T20 Ο—7 δ ppm 1.19-1.38 {m, 2Η), 1.52-1,72 (m, 3Η), 2Μ <s, 6H), 2.03^2,07 {m, 2H), 2.25 (8, m), 2.84 (8, 2H)t 3.24-3.30 <ηι( 2H), 3,79-2.83 (m, 2H), 6.21 <t 1H), 6.87(s*2H> 121 严 U>MS (方法 B) ES,: ΜΙ·Γ* 敦8~~~ it = 1.34 T22 LC*MS (万法r A) iS*: MfT = 344 rtM.27分鐘 T23 L&MS (方法 A) ES+: ΜΗ* = 344 rt=M.19 分鐘 t24 LC"MS (方法 A) ES’: MM、356 rt =1,29分鐘 T25 LOMS (方法 B) ES*:MH* = 343 It = 1,33 分鐘
100 201014819
ne LC.MS (方法_ A) EST: MH* = 315 It = 1,46 分鐘 127 oW LC*MS (方法 B) es*:MH* = 34S rt= 1,10 分鐘 12B LC-MS(方法 A) ES+: MW**329 ft =1.52^# T2B 0^/ LC*MS(方法 B) i ES' MH+ = 315 rt**1.24 分鐘 m 0^/ LX>MS (方法 A) ES+:MH’ = 315 j rt = 1J1分鐘 T31 LC^IS (方法入)ES,: ΜΗ* = 376 ! rt =1.28分鐘 101 201014819 Τ32 LC*MS (方法 A) ES+: ΜΗ+ = 356 rt = 1.36 分鐘 Τ33 LC-MS (方法 A) ES+: ΜΗ" = 386 rt* 1.51分鐘 Τ34 0 Ld(;方法 A) EST: MH+ = 402 ft =142 分鐘 , Τ35 Ύ LC-MS (方法 A) ES' ΜΗ* * 342 rt = 1.21分鐘 Τ36 0 〇 LC-MS (方法 A) ES+: MH* = 378 rt =129分鐘 Τ37 LC^MS(方法 A) ES*: MH,= 341 ft = 144分鐘 Ο Ο 102 201014819
T38 LOWS (方法 A) ES*: MH+ = 359 ft = 1,22 分鐘 T39 LOMS(方法人)EST: MHT=343 rtM.42分鐘 T40 LG*MS (方法 A) ES,ΜΗ· = 317 rt=1,22分鐘 T41 J?7 〇/>^° 0 LC*MS (方法 A) ES+: MH、404 rt=1,41 分鐘 T42 UMI4S(方法 A) ES+. ΜΗΓ = 44β rt-166分鐘 T43 D LC-MS (方法 A) ES,: ΜΗ· = 358 rt = 1.34分鐘 103 201014819 T44 bMS(方法人)ES*: MH+ = 32S It-159^# T4S δ (ΟΜΒΟκίΒ) ppm 1.4S (m, 2H>, 1 ,Sfi (mf 2H>, 2.01 (s, 6H)T 3.0β φτ, s)( 3.37 (m, 2H), 3.87 (m, 2HK 6.75 (a, 1H), 6.04 {brs,1H),7.27(s,2H>. 146 V-N LC-MS (方法 A) ESVlWH* = 354 rt=1.32分鐘 T47 LOMS (方法 A)—.isr: ΜΗ* « 390 rt=1.38分鐘 丨 T4S LC-MS (方法 A) ES+: Μί?*35β It =1.38 T49 0^/ U>hs (;方法 B) ES*: MH+= 31S rt = 1.34分鐘 ❹ ❹ 104 201014819
TSO O^。 LOWS(方法 B) ES*:MH,*329 it =1屈分鐘 T51 /0 卜0 LC~MS(方各 A) ES+: MHT«392 rt=1.36分鐘 T52 LOMS (方法 C) ES*:M4T»299 Rt=4;T5 分鐘 熔點·· Ι65·167 °C T53 cf LC"MS (方法 A) ES,:瞻Γ = 314 rt* 1-09 分鐘 TS4 LC*MS (方法 A) ES·: MH" = 412 rtsl63分鐘 T55 LC«MS(方法 A) ES4: MFT=414 rts 1,61分鐘 105 201014819
106 201014819
107 201014819 Τ67 Ο#3 LOM8(方法 C) ES*:MHT = 37T rtMJS分鐘 ΎΒ8 Ld^is (方法 B) est Μβ = 434 rtM,61分鐘 rm 法 B)政:mh’ s414 rt«1.64分鐘 170 LOMS(方法 B) ES*: MH* = 418 Λ = 1·44分鐘 Τ71 LC^IS(方法 B) ES+: (ΛΙΓ*490, 488, 486 (tM.61分鐘 Τ72 LC*MS(方法 B) ES+: MH+ = 432 rt= 1,49分鐘 Τ73 0 1€也3(方法 B) EST: MH、454,452 rt = 1,55 分鐘 Τ74 LC*MS (方法 B) ES,MhT = 490r 488, 4m rt;1j4分鐘 Ο
108 201014819
175 (方法 B) ET: MH、436 rt=1,48分鐘 T76 [CiS (方法 B) ES’: MH+ = 454r 452 rt*1J6分鐘 T77 LC^MS (方法 B) ES’: ΜΗ* * 494 rts17〇分鐘 T78 L(>MS (方法 B) ES+: ΜΗ·Μ32 rtM.52分鐘 T7§ LC44S (方法 β) E_i*: MH+ -挪 rt =1.47 分鐘 j T8D LOl/IS(方法 B) ES' MH* = 384 rt* 1.38分鐘 m Lc-MS(方法 B) ES、= 3δβ rt=1,2S分鐘 . .......... 109 201014819 782 LOMS (方法 13) ES": ΜΗ,= 432 rt=1,49分鐘 T83 LC>MS (方法 Β) EST: ΜΗ’ = 370 rt = 1.32分鐘 T84 LC*MS (方法 B) ES": ΜΗ4 * 384 rt » 1.39分鐘 TBS &MS(方法 B) £S’: MH+ = 3S8 rt; 1.48分鐘 T86 LCMWIS(方法 0) ESS MH+ = 4S2, 490, m rt-1.71分鐘 T87 LC-MS (方法 B) ES·: MHT = 406,404 rt* 1,42 分鐘 T88 LC-MS (方灰 B) ES’: MH‘ = 382 rt=136分鐘
110 201014819
T89 LC*MS(方法 B) es+: Mtr = 424 rt=i.邱分鐘 卿 LC*MS (方法:B) ES+: ΜΗ" = 408 rt =1,38 分鐘 T91 IG-MS (方法 B)献 MK" = 454 rtsl60分鐘 T92 LC*MS (方法 B) ET: 490,488 rt* 1.70分鐘 T93 T94 LC4/IS (方法 B)l8*: ΜΗ、392 rt^M-34分鐘 T95 A-, LC*MS(方法 B) EST: Ι\#Γ = 406 rt = 1.39 分鐘 111 201014819 T96 o^Nv-/ LC*MS (方法 B) ES’: MH’ = 434 rtM.60分鐘 197 LC*MS (方法 B) ES,: _·Γ = 448 n =1,47 T98 LOMS(方法 Ε;) ES5 MHTs372 ft =1.40 分鐘 m LC"MS (方法·Β) ES’: MH+ = 486 rt=1-60分鐘 TlOO LOWS (方法 B) ES4: _T » 427 rt-1.31 Tioi io^ LC*MS (方法 B) ES,: ΜΗ· = 39β rt = 1.51分鐘 Π02 U>MS (方法 B) EST: ΜΗ1 = 384 rt*1.51分鐘
112 201014819
Γ103 LC*MS(方法 13) ES4: MH* = 422i 420 rt=1,S2分鐘 T104 id*MS (方法 B) ET: MHS3S6 rt=t,41 T105 LC>MS (方法 B) ES5 MH、462,460, 45β rt» 1,64分鐘 Π06 LOMS (方法 B) ES^ MfT=SQ9t§07t 606 | rtw 1*S8 分鐘 T107 >vo^ LC4A$(^r yt B) ES^ MH+ ^ 400 丨 rtss 1,54 分鐘 T1D8 LOWS (方法 B) ES+: ΜΗ、3邸 rt = 1.46分鐘 T109 1 LC*MS (方法 B) ES': = 468 rts=1.e5 分鐘 113 201014819 mo LOMS (方法 B) ES,: MH* = 424 rt=1.44 分鐘 mi U>MS(方法 β) ES*: MhT = 455,453 分鐘 Π12 iC4^(方法 B〗ES*: MHT = 446 rt 要 *L86 分 T113 LC-MS(方法 B) ES,MH,*398 it = 1-44 分鐘 T114 Lt^i^S (方法 B) ES’: MHT * 410 rt = *LS0分鐘 ms Ld~MS〔方法 B) KT: MH、402 rt«1.56 分鐘 Tllf LG涵(方1去 B) ES,MH,= 444 rt= t55分鐘
114 201014819
TU7 LOWS(方法 B) ES+: MH+ = 478 ft»1,54 分鐘 T118 LC^/IS (¾法 B) EST: _4 == 437 rt = 1.35 分鐘 T119 LC*MS(方法 B) ES*: MhT = 423 ft =1.42 分鐘 T120 LC^MS(方法 B) 藿425 一 rt®1,51 分鐘 T121 [C»MS (方法 B) ES*: ΜΗ* = 436 rt=1,36 分鐘 T122 LC-MS (方法 1) ES,: MH+ = 432 rt = 1J52 分 T123. I LC*MS (方法 B) ES+: MH’ *416— rtMJg分鐘 115 201014819 T124 ϋ>Μ8 (^^·ΰ) ES*. MH^-472 «*1,35 T125 (方各运)ES^ MH’:45& 一 rt»1,87分鐘 T126 T127 0 LCMMS(方法 A) ES〜MHV =的e rt* 1-12分鐘 T12S 0 LC*MS(方法 A) ES*: MH,= 41«3 rt=1.21 分鐘 · Π29 0 LC*MS (-方法 A) ES*: ΜΗ’ = 412 rt = 1J4分鐘
116 201014819
117 201014819 LOWS (方法 C) , es,MH* = 446 rt=4.43分鐘 TI36 δ (CD^OD) ppm 1.8-1.5 (m, 6H), 2.07 (s, ocr^ 3H)t 2.08 (s, 3H), 2.67-2.S9 (m, 2H), 3.2 (m, 2H)t 3.35 (m, 2H), 3.9 (m, 2H), 7.22 〇o^° {s, 2H), 7.5S (dr 2H), 7.6? (d, 2H). T137 δ ppm 1,33 (m, 3H), 1.66 (m, 3H), 1^8 (m. 1H), 2.0S (s, 8H), 2.^ {m, 1H), 2,78 (mf 2H), 3.38 (m, 2H), 3.9 (m. 2H), 7.21 ΠΜ O^。 is,2H). δ ppm 1.4 (m, 4H)t t.7 (m, 2H), 1.9 {m. 1H), 2J8 (2 x s, 6H), 2,4 〇>r, 1H), 2,9 (br, 2H>, 3.4 (m, 2H), 3.S7 (m, 2H), 7,14 (m, 1H), 7.2 (m, IN), 7.^ (s, 2H)t 7,32 Τ139 (d, 1H). 7,4 (m, 1H). i〇y? LOMS (方法 C) ES+: MH,s 380 i ft* 3.S8 分鐘 ΤΧ40 UMW1S(方法 A) ES' ΜΗ’ = 368 rt=1,29分鐘 A ί>^° I Τ141
118 201014819
T142 0 LC*MS (方法 A) ES5 MH* = 370 rt»1.昶分鐘 T143 0 LOWS(方法 A) ES\ MH’ = 384 分鐘 T144 n [C^IS(方法 a) ES*: ΜΗ* = 382 rt=1.36分鐘 T14S α々0^。 o 方法 A) es4: MH*s42〇,458 rt= 1.41分鐘 T146 <v°^° o LC*MSi(方备 A) EB,: MH^^O it = 1.33 分鐘 T147 0 LOMS (牙法 A) EST: =沾4 rt=1.31 119 201014819 T148 %, LOMS (方法 A) ES,: MH* = 423 rt*1_27分鐘 T149 LOMS (方法 A) ES,: ΜΗ* * 421 rt-1.66分鐘 TiSO LC^IS (方法 A) · ΕΚ ΜΗ+ = 301 rt=1-82分鐘 nsi ▼ LOMS (方法 A) ES,: ΜΗ* = 391 rt«1.65分鐘 T152 LOWS (方法 A) IES*: ΜΗ* = 329 丨 rt»1.45分鐘 T1S3 L&MS (方法 A)丨 ES·: MH+ = 345 it* 1.38 分鐘
120 201014819
T1S4 —〇 LOMS (方法 A)_ ESYmH、421 it = 1朋分鐘 TI55 —Si LOWS (方法 A) Ε#:ΜΗ+ = 411 rt = 1,81分鐘 use LOMS (方法 A) ES*: rtM.37分鐘 T15? δ ppm 1.6 (m, 2H), 2.10 (m, 2H), 2.20 (s. QH), 2.40 (m, 2H), 2.90 (br, 2H), 3.40 (m, f HJ, 3.76 {m, tH>, 3.90 (m, 2H), 7 J1 (s, 2H), 7.66 {m, 4H}. T1S8 S ppm 1,60 (m, 2H>, 2.05 2H>, 2·10 (s, 6H), 2.40 (m, 2H), 2.90 (m, 2H), 3.40 (m, 1H), 3 J& <m, 1H), 3.9 (mt 2H)t 7.10 (tt 2H), 7.2S (s, 2H), 75 (mf 2H). T159· δ ppm 1-4 (ibr, iH>, 1 .S (br, 2H), 2.09 (s. 3H), 2.1 (s, 3H), 222 {ύ, 2H), 2.6 (m, 2H), 3.2 {m, 1H), 3.62 {m, 1H), 3.76 (m, 2H), 7.25 <s. 2H), 7.32 (d, 1H), 7.39 (% 2H)p7.52(d,2H). 121 201014819 ηβο δ ppm 1.33 (m, 3H), 1.4 (m, 1H), 1.56 (m, 1H), 1.95 (m, 1H)t 2.01 (8,3H), 2,03 {s( 3H>, 2.10 (m, 1H), 2.29-2J7 (m, 2H), 2.75-2.S7 (m, 2H), 3.3 (m, 1H)t 3.69 (m, 1H). 3.82《m, 2H), 7J7 (s, 2H}, Τ16Ι TC^1S(^r^ A) ES": MH* -442 rt=166分鐘 Τ162 ? rv/^° (方法 A) ES’: MH’*396 rt =1.51分鐘 Τ163 LC*MS (方法 A) ES,: MH+ = h〇 rt = 1.59分鐘 Τ164 LOMS (方法 A) l ES*: =含01 ft· 1.31 分鐘 了 16S LG4/1S (方法 A) ES·: MH+ = 331 ft =1.27 分鐘 Τ166 LOMS (方法 A) Er:MhT = 341, ~ 343,345 rt* 1.39分鐘
122 201014819
了 167 LC4iS (方法 A) 1ES+: ΜΗ* = 321 · 323 It* 1.39 分鐘 Ties 00-MS(方法 A) ES+: MH,s273 rtM.26分鐘 T169 δ p(OT 1J3 (m, 3H), 1 朋(m,3H), 1,8 cm, 1H), 2,08 (s, 3H), 2,09 (s, 3H), 2,35 (d, 1H), 2.85 <d, 2H), 3 J9 (m, 2H), 3,97 (m, 2H), 7,09 (st 2H). Τ17Θ S pfsm 1.42 (mt 3H), 1.70 (m. 3H), 1.89 (in, 1H), 2.08 (st 3H>, 2.10 (s, 3H), 2,34 (d. 1H), 2.85 (d, 2H), 3,39 (m, 2H>, 3.97 (m, 2H)( m <d, 2H). 1171 104胳(方法 C) Ε#:ΜΗ" = 305 rt = 3,37分鐘 7172 LC-WS (方法 A) ES": ΜΗ* * 425 rt=1.83分鐘 T173 0J^ δ ppm 0.65 (m, 2H), 0.9 (m, 2H), 141 (m, 3H), 1.68 (m, 3H), 1.80 (m, 1H), 1 JO (m, 1H), 2Λ7 {s, 6H>, 2.35《br, 1H}, 2.8 (br, 2H), 3.3B (m, 2H), 3,96 (m, 2H), 6.7δ (β,2Η) 123 201014819
表pi 化合物 編號 結構 ^nmr (CDCI3,除非有另外陳 述),或其他的物理數據 124 201014819
P1 δ ppm 1,21 (t, 3H), 1.32-1.47 (m, 3H), 1.61-1.70 (m, 2H), 1.72-1.82 (m, 1H), 1.91-2.02 (m, 1H), 2.42-2.58 (m, 3H), 2.65^2,77 (m, 1H), 3.00 (dd, 1H), 3.35-3.45 (m, 2H), 3.84 (s, 3H), 3.95-4.04 (m, 2H), 7.24 (d, 1H), 7.38-7.41 (m, 2H), 7.42 (<J, 1H), 7.45-7.49 (m, 2H). 7.55 (dd, 1H) P2 〇W S ppm 1.53 (d, 2H),170-1.79 (m, 2H), 1.85 (td, 1H), 2.09 (d, 6H), 2.26 (s, 3H), 2.50 (dd, 1H), 2.73-2,81 (m, 1H), 2.83-2.94 (m, 1H), 3.33-3.48 (m, 2H), 3.61 (d, 1H), 3.74 (s, 3H), 4,01-4.10 (m, 2H), 4.58 (s, 1H), 6.87 (s, 2H) P3 δ ppm t.11 (s, 9H), 1.53 (<J, 2H), 1.69-1.91 (m, 3H), 2.06 (d, 6H), 2.26 (s, 3H), 2.78-2,88 (m, 3H), 2.89 (ddd, 1H), 3.13 (dd, 1H>, 3.33-3.47 (m, 2H), 3.69 (d, 1H), 4.05 (td, 2H)t 4.13 (S, 3H), 6.85 (S, 2H) P4 δ ppm 1.28-1.46 (m, 3H), 1.61-1.70 (m, 2H), 1.70-1.79 (m, 1H), 1.94 (ddd, 1H), 2.08 (d, 6H), 2.26 (s, 3H), 2.44 (<id, 1H), 2.66-2,77 <m, 1H), 2.97 (dd, 1H), 3.35-3.48 (m, 2H), 3 J3 (s, 3H), 3.95-4.05 (m, 2H),6.87<s,2H) P5 δ ppm 1.09 (s, 9H), 1.28-1.46 (m, 3H), 1.59-1.69 (m, 2H), 1.70-1.77 (m, 1H), 1.94 (ddd, 1H), 2,05 (d, 6H), 2.25 (s, 3H), 2.70 (dd, 1H), 276-2,86 {m, 1H), 3.16 (dd, 1H), 3.33-3.45 (m, 2H), 3.91-4.07 (mt 2H), 6.84<$,2H) 125 201014819 Ρβ 0〇^ δ ppm 1.68-1.68 (m, 4Η>, 2.12 (s, βΗ), 227 (s, 3Η), 2.37-2.54 (mt 1Η), 3.09 (d, 2H). 3.49 Ctd, 2H), 3.55 (s, 3H), 3.96-4.07 (m, 2H), 5.92 (d, 1H), β,88 (s, 2H) Ρ7 5 ppm 1.09 (s, 9H)( 1.08-1,86 (m, 2H), 2·昉(d, 6H), 2.07么 15 {mt 2H), 2_2S (s, 3H), 2.35-2,45 (m, 1H), 2,64-2*79 <m, 2H), 3.17 (dd, 1H), 3,40 «it, 1H)S 3.79 (ddd, 1H), 3,89 (ddd, 1H), 3.97 (t, 1H)t 6.84(δ,2Η) Ρ8 δ ppm 1.44-1 .S2 (m, 1H>, (cfdd, 1H), 1.88-185 (m, IH), 1.96-2.03 (m, 2H), 2JQB (d, 6H), 2.26 (s, 3H), 2.44 (ild, 1H), 2.66-2.74 (m, 4H), 2.?6-2,β1 (m, 1H}, 2.82-2.92 (m, 1H). 3.59 (dd, 1H), 3.74 (s, 3H), 4.75 (β, 1H), 6 J7 (s, 2H> Ρ9 5 ppm 1,11 {sf 9H)( 1.70 (ddtJ, 2H), t.97*2.06 (m, 2H), 2.07 (s, 6H)r 2.26 (s, 3H), 2.28-2^0 (m, 1H), 2.62-2.80 (m, 4H), 3.59 (d, 2N), 6.57 (d, 1H), 6.85 (st 2H) ! Ρ10 δ ppm 1.11 (s, 9H), 1.48-1,53 (m, 1H), 174-1.84 (m, 1H), 1.88-1.95 〇ti, 1H), 1.96-2.02 (ro. 2H), 2,05 <d, 6H), 2.26 (st 3H), 2.63-2.73 (m, 4H), 2.T4-2.82 (m, 1H), 2.90 (ddd, 1H), 3.10 (dd, 1H), 3.67 (dd, 1H). 4,32 (s, 1H), 6.8S (s, 2H)
126 201014819
127 201014819
P16 P17 pm P19 P20
O’
'9
LC*MS (方法 A) est ΜΗ· 11 = 1.81 分鐘 LC*MS (方法 A) ES+: MH" = 435 It = 181分鐘 LOMS(方法 A) ES’: MH* = 359 rt = 1,56分鐘
128 201014819
P21 LC-MS (方法 A) iMST: MIT = 373 P22 \ LC4AS (方法 A) ES+: MH,= 415 P23 LOMS (方法 A) ESV MH,= 401 P24 V LC-MS (方法 A) i ES*: MH,= 415 P25 LOMS (方法 A) t ES+: MH<= 385 129 201014819 P26 α〇 LC-MS (方法 A) ES〜ΜΙ·Γ = 421 rt= 1.83 分鐘 P27 LC-MS (方法 A) l Εέ*: MH+ = 393 rt = 1,64 分鐘 P28 LC-N/IS (方法 A) ES' MH+ = 405 rt = 1.66分鐘 P29 〇 O-V LC-IWS (方法 A) ES’: ΜΗ* = 412 rt=1.73 分鐘 P30 (方法 A) ES+: MH+ = 389 rt=1.83 分鐘 ❹
130 201014819
P31 (方法 A) ET: ΜΗΓ**387 Λ=1,7β分鐘 PS2 〇OH LC-MS(^^: B) i ES4: ΜΗ+ = 35Θ~^ rt« 1,26分鐘 P3S LC*MS (方法 A) ET: ΜΙ·Γ = 345 ; P34 d tOMS(方法 A) ES*: ΜΗΤ=Μ1:3 rt = 2.03分鐘 P35 〇r lOMS (方法 B) i ES·: MH+ = 357 rt» 1*44分鐘 一 131 201014819
132 201014819
133 201014819
134 201014819
P52 〇W LC*MS (方沄 A) EST: ΜΗ* * 359 rt=i·艏分鐘 P53 LC*MS (方法 A) ES,: ΜΗ* = 512 it = 2.03 分鐘 P64 LC4s«S(方法 A) ESt MhT = S14 rt=2.03分鐘 PSS Q E〇*MS (方法 A) ES*: MH+ = 448 ft =1.78 分鐘 PS6 Λρ LOMS (方法 A) Ε$·:Μ#β43ΰ rt* 1,54分鐘 135 201014819 P57 LC-MS A) ES*: ΜΗ" = 436 rt* 1,56分鐘 P58 LC-MS (方法 A) ES' _Η,= 440 rt«1.7f分鐘 pm LC*MS (方法 A) ES’: ΜΗ、468 ft = 1,85 分鐘 ΡβΟ !0·«§ (方法 A) £@r: MH+ s 540. 538. 536 rtMJS分鐘 P61 D LC^MS(方法:A) ESVMH* = S20 It* 1.76 分鐘
136 201014819
137 201014819 P67 δ ppm <D20" ·2(Η—40 ㈣,1 胳 185 (mt 4H)( 2,01 (s3 6Η)β 2,15-2.25 (m, 4H)( 2,60-2.70 (m, 2H)# 3^10-3.55 (mf 2H% 3.90-4Ό5 (mr 2H), 6.91 (s, 2H) Ρββ δ ppm fl52〇) 1.20-1.40 (m, 3H), 1,60-1.85 <m, 4H), 2.01 (s, 6H), 2,15-2.25 (m, 2.60>2;70 (m, 2H), 3.40-3.55 {m. 2H), 3.9iW.0S (m, 2H). 6.91 (s, 2H) Ρ69 (方法 A) ES*: Έη· = 327 ~ rt=1.54分鐘 ΡΤ0 LOWS (方法 A) ES,: MHT»405 ~ ft =1.75 分鐘 Ρ71 ? LC-MS (方沄 A) ES*: ΜΗ’ = 435 it = 1.81 分鐘
下表1至102之化合物可以類似方式獲得。 表1涵蓋262種下列類型的化合物: 138 201014819
R2 R3 及R4皆係如下表1所述:
其中 G,R5 ’ R6,R7,R8 及 R9 皆為氮,且 R1,R2,R3 化合物編號 R1 R2 R3 R4 1.001 ch3 H H H 1.002 ch3 ch3 H H 1.003 ch3 H ch3 H 1.004 ch3 H H ch3 1.005 ch3 ch3 ch3 H 1.006 ch3 ch3 H ch3 1.007 ch3 ch3 ch3 ch3 1.008 ch3 Cl H H 1.009 ch3 Cl H ch3 1.010 ch3 Cl H och3 1.011 ch3 H Cl H 1.012 ch3 H H Cl 1.013 ch3 ch3 Cl H 1.014 ch3 ch3 H Cl 1.015 ch3 H Cl ch3 139 201014819 1.016 ch3 ch3 Cl ch3 1.017 ch3 Br H H 1.018 ch3 Br H ch3 1.019 ch3 Br H och3 1.020 ch3 H Br H 1.021 ch3 H H Br 1.022 ch3 ch3 Br H 1.023 ch3 ch3 H Br 1.024 ch3 H Br ch3 1.025 ch3 ch3 Br ch3 1.026 ch3 ch3o H H 1.027 ch3 ch3o H ch3 1.028 ch3 ch3o H Cl 1.029 ch3 ch3o H Br 1.030 ch3 ch3 ch2o H H 1.031 ch3 ch3 ch2o H ch3 1.032 ch3 ch3 ch2o H Cl 1.033 ch3 ch3 ch2o H Br 1.034 ch3 H ch3o H 1.035 ch3 H H CH3 0 1.036 ch3 ch3 CH3〇 H 1.037 ch3 ch3 H CH3 0 1.038 ch3 H CH3〇 ch3 1.039 ch3 ch3 ch3o ch3 140 201014819
1.040 ch3 -ch=ch2 Η ch3 1.041 ch3 ch3 Η -ch=ch2 1.042 ch3 -C.CH Η ch3 1.043 ch3 ch3 Η -C.CH 1.044 ch3 -ch=ch2 Η -ch=ch2 1.045 ch3 ch2 ch3 Η ch3 1.046 ch3 苯基 Η ch3 1.047 ch3 2-氟苯基 Η ch3 1.048 ch3 2-氣苯基 Η ch3 1.049 ch3 2-三氟曱基 苯基 Η ch3 1.050 ch3 2 -硝基苯基 Η ch3 1.051 ch3 2-曱基苯基 Η ch3 1..052 ch3 2-甲磺醯基 苯基 Η ch3 1.053 ch3 2-氰基苯基 Η ch3 1.054 ch3 3-氟苯基 Η ch3 1.055 ch3 3-氯苯基 Η ch3 1.056 ch3 3-三氟曱基 苯基 Η ch3 1.057 ch3 3-硝基苯基 Η ch3 1.058 ch3 3-甲基苯基 Η ch3 1.059 ch3 2-甲磺醯基 苯基 Η ch3 141 201014819
1.060 ch3 3-氰基苯基 Η ch3 1.061 ch3 4-氟苯基 Η ch3 1.062 ch3 4-氣苯基 Η ch3 1.063 ch3 4-溴苯基 Η ch3 1.064 ch3 4-二氟甲氧 基苯基 Η ch3 1.065 ch3 2-氟-4-氣 苯基 Η ch3 1.066 ch3 2-氣-4-氣 苯基 Η ch3 1.067 ch3 2-甲基-4-氣苯基 Η ch3 1.068 ch3 4-三氟甲基 苯基 Η ch3 1.069 ch3 4-硝基苯基 Η ch3 1.070 ch3 4-甲基苯基 Η ch3 1.071 ch3 4-甲磺醯基 苯基 Η ch3 1.072 ch3 4-氰基苯基 Η ch3 1.073 ch3 Η 苯基 H 1.074 ch3 Η 2-氟苯基 H 1.075 ch3 Η 2-氣苯基 H 1.076 ch3 Η 2-三氟甲基 苯基 H
142 201014819
1.077 ch3 H 2-硝基苯基 Η 1.078 ch3 H 2-曱基苯基 Η 1.079 ch3 H 2-甲磺醯基 苯基 Η 1.080 ch3 H 2-氰基苯基 Η 1.081 ch3 H 3-氟苯基 Η 1.082 ch3 H 3-氣苯基 Η 1.083 ch3 H 3-三氟曱基 苯基 Η 1.084 ch3 H 3-硝基笨基 Η 1.085 ch3 H 3-曱基苯基 Η 1.086 ch3 H 2-甲磺醢基 苯基 Η 1.087 ch3 H 3-氰基苯基 Η 1.088 ch3 H 4-氟苯基 Η 1.089 ch3 H 4-氣苯基 Η 1.090 ch3 H 4-溴苯基 Η 1.091 ch3 H 4-二氟曱氧 基苯基 Η 1.092 ch3 H 2-氟-4-氣 苯基 Η 1.093 ch3 H 2-氣-4-氯 苯基 Η 1.094 ch3 H 2-曱基-4- Η 143 201014819 氣苯基 1.095 ch3 H 4-三氟甲基 笨基 Η 1.096 ch3 H 4-硝基苯基 Η 1.097 ch3 H 4-曱基苯基 Η 1.098 ch3 H 4-甲磺醯基 苯基 Η 1.099 ch3 H 4-氰基苯基 Η 1.100 ch2 ch3 H Η Η 1.101 ch2 ch3 ch3 Η Η 1.102 ch2 ch3 H ch3 Η 1.103 ch2 ch3 H Η ch3 1.104 ch2 ch3 ch3 ch3 Η 1.105 ch2 ch3 ch3 Η ch3 1.106 ch2 ch3 ch3 ch3 ch3 1.107 ch2 ch3 Cl Η Η 1.108 ch2 ch3 Cl Η ch3 1.109 ch2 ch3 Cl Η och3 1.110 ch2 ch3 H C1 Η 1.111 ch2 ch3 H Η Cl 1.112 ch2 ch3 ch3 C1 Η 1.113 ch2 ch3 ch3 Η Cl 1.114 ch2 ch3 H C1 ch3 1.115 ch2 ch3 ch3 C1 ch3
144 201014819 1.116 ch2 ch3 Br H H 1.117 ch2 ch3 Br H ch3 1.118 ch2 ch3 Br H och3 1.119 ch2 ch3 H Br H 1.120 ch2 ch3 H H Br 1.121 ch2 ch3 ch3 Br H 1.122 ch2 ch3 ch3 H Br 1.123 ch2 ch3 H Br ch3 1.124 ch2 ch3 ch3 Br ch3 1.125 ch2 ch3 ch3o H H 1.126 ch2 ch3 ch3o H ch3 1.127 ch2 ch3 ch3o H Cl 1.128 ch2 ch3 ch3o H Br 1.129 ch2 ch3 ch3 ch2o H H 1.130 ch2 ch3 ch3 ch2o H ch3 1.131 ch2 ch3 ch3 ch2o H Cl 1.132 ch2 ch3 ch3 ch2o H Br 1.133 ch2 ch3 H ch3o H 1.134 ch2 ch3 H H CH3 0 1.135 ch2 ch3 ch3 ch3o H 1.136 ch2 ch3 ch3 H CH3 0 1.137 ch2 ch3 H ch3o ch3 1.138 ch2 ch3 ch3 ch3o ch3 1.139 ch2 ch3 -ch=ch2 H ch3 145 201014819
1.140 ch2 ch3 ch3 Η -ch=ch2 1.141 ch2 ch3 -C.CH Η ch3 1.142 ch2 ch3 ch3 Η -C.CH 1.143 ch2 ch3 -ch=ch2 Η -ch=ch2 1.144 ch2 ch3 ch2 ch3 Η ch3 1.145 ch2 ch3 苯基 Η ch3 1.146 ch2 ch3 2-氟苯基 Η ch3 1.147 ch2 ch3 2-氣苯基 Η ch3 1.148 ch2 ch3 2-三氟曱基 苯基 Η ch3 1.149 ch2 ch3 2-硝基苯基 Η ch3 1.150 ch2 ch3 2-甲基苯基 Η ch3 1.151 ch2 ch3 2-曱磺醯基 苯基 Η ch3 1.152 ch2 ch3 2-氰基苯基 Η ch3 1.153 ch2 ch3 3-氟苯基 Η ch3 1.154 ch2 ch3 3-氣苯基 Η ch3 1.155 ch2 ch3 3 -三氟甲基 苯基 Η ch3 1.156 ch2 ch3 3-硝基苯基 Η ch3 1.157 ch2 ch3 3-甲基苯基 Η ch3 1.158 ch2 ch3 2-曱磺醯基 笨基 Η ch3 1.159 ch2 ch3 3-氰基苯基 Η ch3 146 201014819
1.160 ch2 ch3 4-氟苯基 Η ch3 1.161 ch2 ch3 4-氣苯基 Η ch3 1.162 ch2 ch3 4-溴苯基 Η ch3 1.163 ch2 ch3 4-二氟甲氧 基苯基 Η ch3 1.164 ch2 ch3 2-氣-4-氣 苯基 Η ch3 1.165 ch2 ch3 2-氣-4-氯 苯基 Η ch3 1.166 ch2 ch3 2-甲基-4-氣苯基 Η ch3 1.167 ch2 ch3 4-三氟甲基 苯基 Η ch3 1.168 ch2 ch3 4-硝基苯基 Η ch3 1.169 ch2 ch3 4-曱基苯基 Η ch3 1.170 ch2 ch3 4-曱磺醯基 苯基 Η ch3 1.171 ch2 ch3 4-氰基苯基 Η ch3 1.172 ch2 ch3 Η 苯基 H 1.173 ch2 ch3 Η 2-氟苯基 H 1.174 ch2 ch3 Η 2-氣苯基 H 1.175 ch2 ch3 Η 2-三氟甲基 苯基 H 1.176 ch2 ch3 Η 2-硝基苯基 H 147 201014819
1.177 ch2 ch3 H 2-曱基苯基 Η 1.178 ch2 ch3 H 2-曱磺醯基 苯基 Η 1.179 ch2 ch3 H 2-氟基苯基 Η 1.180 ch2 ch3 H 3-氟笨基 Η 1.181 ch2 ch3 H 3-氣苯基 Η 1.182 ch2 ch3 H 3-三氟甲基 苯基 Η 1.183 ch2 ch3 H 3-硝基苯基 Η 1.184 ch2 ch3 H 3 -甲基苯基 Η 1.185 ch2 ch3 H 2-甲磺醯基 苯基 Η 1.186 ch2 ch3 H 3-氰基苯基 Η 1.187 ch2 ch3 H 4-氟苯基 Η 1.188 ch2 ch3 H 4-氣苯基 Η 1.189 ch2 ch3 H 4-溴苯基 Η 1.190 ch2 ch3 H 4-二氟甲氧 基苯基 Η 1.191 ch2 ch3 H 2-氟-4-氣 苯基 Η 1.192 ch2 ch3 H 2 -氣-4 -氯 苯基 Η 1.193 ch2 ch3 H 2-曱基-4-氣苯基 Η 148 201014819 1.194 ch2 ch3 H 4-三氟甲基 苯基 Η 1.195 ch2 ch3 H 4-硝基苯基 Η 1.196 ch2 ch3 H 4-甲基苯基 Η 1.197 ch2 ch3 H 4-甲磺醯基 苯基 Η 1.198 ch2 ch3 H 4-氰基苯基 Η 1.199 ch2 ch3 ch3 Η ch2 ch3 1.200 ch2 ch3 ch2 ch3 Η ch2 ch3 1.201 ch2 ch3 Cl Η ch2 ch3 1.202 ch2 ch3 Br Η ch2 ch3 1.203 ch2 ch3 N〇2 Η ch2 ch3 1.204 ch2 ch3 ch3o Η ch2 ch3 1.205 ch2 ch3 ch3s Η ch2 ch3 1.206 ch2 ch3 ch3so2 Η ch2 ch3 1.207 ch2 ch3 ch2= ch Η ch2 ch3 1.208 ch2 ch3 -C.CH Η ch2 ch3 1.209 ch2 ch3 苯基 Η ch2 ch3 1.210 ch2 ch3 2-氟苯基 Η ch2 ch3 1.211 ch2 ch3 2-氣苯基 Η ch2 ch3 1.212 ch2 ch3 2-三氣*曱基 苯基 Η ch2 ch3 1.213 ch2 ch3 2-硝基苯基 Η ch2 ch3 1.214 ch2 ch3 2-甲基苯基 Η ch2 ch3 149 201014819 1.215 ch2 ch3 2-甲磺醯基 苯基 Η ch2 ch3 1.216 ch2 ch3 2-氰基苯基 Η ch2 ch3 1.217 ch2 ch3 3-氟苯基 Η ch2 ch3 1.218 ch2 ch3 3-氣苯基 Η ch2 ch3 1.219 ch2 ch3 3-三氟甲基 苯基 Η ch2 ch3 1.220 ch2 ch3 3-硝基苯基 Η ch2 ch3 1.221 ch2 ch3 3-曱基苯基 Η ch2 ch3 1.222 ch2 ch3 2-甲磺醯基 苯基 Η ch2 ch3 1.223 ch2 ch3 3-氟基苯基 Η ch2 ch3 1.224 ch2 ch3 4-氟苯基 Η ch2 ch3 1.225 ch2 ch3 4-氣苯基 Η ch2 ch3 1.226 ch2 ch3 4-溴苯基 Η ch2 ch3 1.227 ch2 ch3 4-二氟曱氧 基苯基 Η ch2 ch3 1.228 ch2 ch3 2-氟-4-氣 苯基 Η ch2 ch3 1.229 ch2 ch3 2-氣-4-氣 苯基 Η ch2 ch3 1.230 ch2 ch3 2-甲基-4-氣苯基 Η ch2 ch3 1.231 ch2 ch3 4-三氟曱基 Η ch2 ch3 150 201014819
苯基 1.232 ch2 ch3 4-硝基苯基 Η ch2 ch3 1.233 ch2 ch3 4-甲基苯基 Η ch2 ch3 1.234 ch2 ch3 4-甲磺醯基 苯基 Η ch2 ch3 1.235 ch2 ch3 4-氰基苯基 Η ch2 ch3 1.236 och3 Η 苯基 H 1.237 och3 Η 2-氟苯基 H 1.238 och3 Η 2-氣苯基 H 1.239 och3 Η 2-三氟甲基 苯基 H 1.240 och3 Η 2-硝基苯基 H 1.241 och3 Η 2-曱基苯基 H 1.242 och3 Η 2-曱磺醯基 苯基 H 1.243 och3 Η 2-氰基苯基 H 1.244 OCHs Η 3-氟苯基 H 1.245 och3 Η 3-氣苯基 H 1.246 och3 Η 3-三氟曱基 苯基 H 1.247 och3 Η 3-硝基苯基 H 1.248 och3 Η 3-曱基苯基 H 1.249 och3 Η 2-曱磺醯基 苯基 H 151 201014819 1.250 och3 H 3-氰基苯基 Η 1.251 och3 H 4-氟苯基 Η 1.252 och3 H 4-氣苯基 Η 1.253 och3 H 4 - >臭苯基 Η 1.254 och3 H 4-二氟曱氧 基苯基 Η 1.255 och3 H 2-氟-4-氣 苯基 Η 1.256 och3 H 2-氣-4-氣 苯基 Η 1.257 och3 H 2-曱基-4-氣苯基 Η 1.258 och3 H 4-三氟曱基 苯基 Η 1.259 och3 H 4-硝基苯基 Η 1.260 och3 H 4-曱基苯基 Η 1.261 och3 H 4-曱磺醯基 笨基 Η 1.262 och3 H 4-氱基苯基 Η
表2涵蓋262種下列類型的化合物: 152 201014819
R2 R3 其中G,R5,R6,R8及R9皆為氫,R7為甲基且R1, R2,R3及R4皆係如表1所述。 表3涵蓋262種下列類型的化合物:
其中G,R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表4涵蓋262種下列類型的化合物:
其中 σ,R5,R6,R7,R8 及 R9 皆為氯,且 R1,R2,R3 及R4皆係如表1所述。 表5涵蓋262種下列類型的化合物: 153 201014819
其中G,R5,R6,R8及R9為氫,R7為曱基且R1,R2, R3及R4皆係如表1所述。 表6涵蓋262種下列類型的化合物:
❹ 其中G,R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表7涵蓋262種下列類型的化合物:
R2 R3
其中 G,R5,R6,R7,R8 及 R9 皆為氫且 R1,R2,r3 及R4皆係如表1所述。 表8涵蓋262種下列類型的化合物: 154 201014819
其中G,R5,R6,R8及R9為氫,R7為曱基且R1,R2, R3及R4皆係如表1所述。 表9涵蓋262種下列類型的化合物:
R2,R3及R4皆係如表1所述。
表1 0涵蓋262種下列類型的化合物:
其中 G , R5 , R6,R7 ’ R8 及 R9 皆為氫且 R1,R2,r3 及R4皆係如表1所述。 表11涵蓋262種下列類型的化合物: 155 201014819
其中G,R5 ’ R6,R8及R9為氫,R7為曱基且R1,R2, R3及R4皆係如表1所述。
表12涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。
表13涵蓋262種下列類型的化合物:
R2 其中 G,R5,R6 , R7,R8 及 R9 皆為氮,且 R1,R2,R3 及R4皆係如表1所述。 表14涵蓋262種下列類型的化合物: 156 201014819
其中G,R5,R6,R8及R9為氯,R7為曱基且R1,R2, R3及R4皆係如表1所述。 表1 5涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表1 6涵蓋262種下列類型的化合物:
其中 G,R5 , R6,R7 , R8 及 R9 皆為氮,且 R1,R2,R3 及R4皆係如表1所述。 表1 7涵蓋262種下列類型的化合物: 157 201014819
其中G,R5,R6,R8及R9為氫,R7為曱基且R1,R2, R3及R4皆係如表1所述。 表1 8涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表19涵蓋262種下列類型的化合物:
其中 <3,R5,R6,R7,R8 及 R9 皆為氮,且 R1,R2,R3 及R4皆係如表1所述。 表20涵蓋262種下列類型的化合物: 158 201014819
其中σ,R5,R6,R8及R9為氮,R7為曱基且R1,R2, R3及R4皆係如表1所述。 表21涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為曱基且R1,R2, R3及114皆係如表1所述。 表22涵蓋262種下列類型的化合物:
R2,R3 及R4皆係如表1所述 表23涵蓋262種下列類型的化合物: 159 201014819
I
R3及R4皆係如表1所述。 表24涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表25涵蓋262種下列類型的化合物:
其中 G,R5,R6,R7,R8 及 R9 皆為氮,且 R1,R2 , R3 及R4皆係如表1所述。 表26涵蓋262種下列類型的化合物: 160 201014819
其中G,R5,R6,R8及R9為氫,R7為曱基且R1,R2 R3及R4皆係如表1所述。 表27涵蓋262種下列類型的化合物:
❹ 其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表28涵蓋262種下列類型的化合物:
R2,R— 及R4皆係如表1所述 表29涵蓋262種下列類型的化合物: 161 201014819
R3 其中G,R5,R6,r8及R9為氫’ R7為甲基且Ri,r2, R3及R4皆係如表1所述。 表30涵蓋262種下列類型的化合物:
Q r3及R4皆係如表1所述。 表3 1涵蓋262種下列類型的化合物:
且R1 R2,R: ❹ 表32涵蓋262種下列類型的化合物: 162 201014819
R2 R3 \^o 其中G,R5,R6,R8及R9為氮,R7為甲基且R1,R2 , R3及R4皆係如表1所述。 表33涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為曱基且R1,R2, R3及R4皆係如表1所述。 表34涵蓋262種下列類型的化合物:
其中 G,R5,R6,R7,R8 及 R9 皆為氮,且 R1,R2,R3 及R4皆係如表1所述。 表35涵蓋262種下列類型的化合物: 163 201014819
曱基且R1,R2, 其中G,R5,R6,R8及R9為氮,R7為 R3及R4皆係如表1所述。 表36涵蓋262種下列類型的化合物:
R2 R3 甲基且R1,R2, 其中G及R5,R8及R9為氫,R6及R7 J R3及R4皆係如表1所述。 表37涵蓋262種下列類型的化合物: 一 R2
R3 其中σ,R5,R6,R7,R8及R9皆為氮 及R4皆係如表1所%。 ,且 Ri,R2,R3 ◎ 表38涵蓋262種下列類型的化合物: 164 201014819
其中G,R5,R6,R8及R9為氮,R7為甲基且R1 , R2, R3及R4皆係如表1所述。 表39涵蓋262種下列類型的化合物:
R3及R4皆係如表1所述。 表40涵蓋262種下列類型的化合物:
R2 R3 其中 G,R5,R6,R7,Rs 及 R9 皆為氮,且 R1,R2,R3 及R4皆係如表1所述。 表41涵蓋262種下列類型的化合物: 165 201014819
R2 R3 其中G,R5,R6 , R8及R9為氮,R7為甲基且R1,R2, R3及R4皆係如表1所述。 表42涵蓋262種下列類型的化合物:
R2 R3 其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表43涵蓋262種下列類型的化合物:
R2 R3
其中 G,R5,R6,R7,R8 及 R9 皆為氮,且 R1,r2 ’ R3 及R4皆係如表1所述。 表44涵蓋262種下列類型的化合物: 166 201014819
其中G,R5,R6 ’ R8及R9為氮,R7為甲基且R1,R = R3及R4皆係如表1所述。 表45涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為曱基且R1,R: R3及R4皆係如表1所述。 表46涵蓋262種下列類型的化合物:
❹ 其中 G,R5,R6,R7,R8 及 R9 皆為氯,且 R1,R2,R3 及R4皆係如表1所述。 表47涵蓋262種下列類型的化合物: 167 201014819
R2 R3 s 曱基且R1,R2, 其中G,R5,R6,R8及R9為氮,R7為 R3及R4皆係如表1所述。 表48涵蓋262種下列類型的化合物:
❹ 其中G及R5,R8及R9為氫,R6及R7 R3及R4皆係如表1所述。 表49涵蓋262種下列類型的化合物: 甲基且R1,R2,
,且 R1,R2,R3 及R4皆係如表1所述。 表50涵蓋262種下列類型的化合物: 168 201014819
R2 R3 其中G,R5,R6,R8及R9為氫,R7為甲基且R1,R2 R3及R4皆係如表1所述。 表5 1涵蓋262種下列類型的化合物:
R3及R4皆係如表1所述。
G 表52涵蓋262種下列類型的化合物: rO «2
其中(3,R5,R6,R7,R8 及 R9 皆為氫,且 R1,R2,R3 及R4皆係如表1所述。 169 201014819 表53涵蓋262種下列類型的化合物:
其中G,R5,R6,R8及R9為氮,R7為曱基且R1 ’ R2, R3及R4皆係如表1所述。 表54涵蓋262種下列類型的化合物: ©
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表55涵蓋262種下列類型的化合物:
其中 G,R5,,R7,r8 及 R9 皆為氫,且 R1,R2,r3 170 201014819 及R4皆係如表1所述。 表56涵蓋262種下列類型的化合物:
R2 R3 0々 其中G,R5,R6,R8及R9為氮,R7為甲基且R1,R2, φ R3及R4皆係如表1所述。 表57涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為f基且R1,R2, R3及R4皆係如表1所述。 表58涵蓋262種下列類型的化合物: 171 201014819
其中 G,R5,R6,R7,R8 及 R9 皆為氫,且 R1,R2,R3 及R4皆係如表1所述。 表59涵蓋262種下列類型的化合物:
其中G,R5,R6,R8及R9為氫,R7為曱基且R1,R2, R3及R4皆係如表1所述。 ◎ 表60涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為曱基且R1,R2 ’ R3及R4皆係如表1所述。 表61涵蓋262種下列類型的化合物: 172 201014819
其中 G,R5 ’ R6,R7,R8 及 R9 皆為氮,且 R1,R2,R3 及R4皆係如表1所述。 表62涵蓋262種下列類型的化合物:
Ο 其中G,R5,R6,Rs及R9為氯,R7為甲基且R1,R2, R3及R4皆係如表1所述。 d 表63涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為曱基且R1,R2, R3及R4皆係如表1所述。 173 201014819 表64涵蓋262種下列類型的化合物:
,且 R1,R2,R3 及R4皆係如表1所述。 表65涵蓋262種下列類型的化合物:
R2 R3 曱基且R1,R2, 其中σ,R5,R6,R8及R9為氫’ R7為 R3及R4皆係如表1所述。 表66涵蓋262種下列類型的化合物:
Ο R2 R3 曱基且R1,R2,
其中G及R5,R8及R9為氫,R6及R7 J 174 201014819 R3及R4皆係如表1所述。 表67涵蓋262種下列類型的化合物:
R2 R3 © 沒 R2,R3 其中G,R5,R6,R7,R8及R9皆為氮,且R1 及R4皆係如表1所述。 表68涵蓋262種下列類型的化合物:
R2 R3 其中G,R5,R6,R8及R9為氮,R7為甲基且R1,R2, R3及R4皆係如表1所述。 表69涵蓋262種下列類型的化合物: 175 201014819
// O R2 R3 其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表70涵蓋262種下列類型的化合物:
其中(3,R5,R6,R7,R8 及 R9 皆為氫,且 R1,R2,r3 及R4皆係如表1所述。
表71涵蓋262種下列類型的化合物:
其中G,R5,R6,R8及R9為氮,R7為甲基且R1,R2, R3及R4皆係如表1所述。 表72涵蓋262種下列類型的化合物: 176 201014819
其中G及R5,R8及R9為氫,R6及R7為曱基且R1,R2, R3及R4皆係如表1所述。
表73涵蓋262種下列類型的化合物:
其中 G,R5,R6,R7,R8 及 R9 皆為氮,且 R1 , R2,R3 及R4皆係如表1所述。
表74涵蓋262種下列類型的化合物:
其中G,R5,R6,R8及R9為氫,R7為曱基且R1,R2, R3及R4皆係如表1所述。 177 201014819 表75涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。
表76涵蓋262種下列類型的化合物:
R2 R3 ° 〇 其中(},R5,R6,R7,R8 及 R9 皆為氫,且 R1,R2,R3 及R4皆係如表1所述。 表77涵蓋262種下列類型的化合物:
R2 R3 其中G,R5,R6,R8及R9為氫,R7為甲基且R1 ’ R2 ’ 178 201014819 Λ R3及R4皆係如表1所述。 表78涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7」 R3及R4皆係如表1所述。 表79涵蓋262種下列類型的化合物: 曱基且R1,R2,
R2 R3 其中G,R5,R6,R7,R8及R9皆為 及R4皆係如表1所述。 表80涵蓋262種下列類型的化合物 氫 ,且 R1,R2,R3
其中G,R5,R6,R8及R9為氮,R7為 甲基且R1,R2, 179 201014819 R3及R4皆係如表1所述。 表8 1涵蓋262種下列類型的化合物:
,R2 R3及R4皆係如表1所述。 表82涵蓋262種下列類型的化合物:
R3 R2 ◎ 其中 G,R5,R6 , R7,R8 及 R9 皆為氫,且 R1,R2,r3 及R4皆係如表1所述。 表83涵蓋262種下列類型的化合物:
R2 180 201014819 , 其中G,R5,R6 , R8及R9為氫,R7為甲基且R1,R2, R3及R4皆係如表1所述。 表84涵蓋262種下列類型的化合物:
R2 R3 e 其中G及R5,R8及R9為氫,R6及R7為曱基且R1,R2, R3及R4皆係如表1所述。 表85涵蓋262種下列類型的化合物:
R2 ❿ 〜0' 其中 G,R5,R6,R7,R8 及 R9 皆為氮,且 Rl , R2,R3 及R4皆係如表1所述。 表86涵蓋262種下列類型的化合物: 181 201014819
l ' R2 R0 --〇 曱基且R1,R2, 其中G,R5,R6,R8及R9為氫,R7為 R3及R4皆係如表1所述。 表87涵蓋262種下列類型的化合物:
R2 R3 甲基且R1,R2, 其中G及R5,R8及R9為氫,R6及R7 ^ R3及R4皆係如表1所述。 表88涵蓋262種下列類型的化合物:
,且 Ri,R2,R3 其中G,R5,R6,R7,R8及R9皆為氮 及R4皆係如表1所述。 表89涵蓋262種下列類型的化合物: 182 201014819
其中G,R5,R6,R8及R9為氮,R7為甲基且R1,R2, R3及R4皆係如表1所述。
表90涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表91涵蓋262種下列類型的化合物:
R2 R3 其中 G,R5,R6,R7,R8 及 R9 皆為氯,且 R1,R2,R3 及R4皆係如表1所述。 183 201014819 表92涵蓋262種下列類型的化合物:
其中G,R5,R6,R8及R9為氫,R7為甲基且R1,R2, R3及R4皆係如表1所述。 表93涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表94涵蓋262種下列類型的化合物:
其中 G,R5,R6,R7,R8 及 R9 皆為氯,且 R1,R2,R3 184 201014819 ' 及R4皆係如表1所述。 ' 表95涵蓋262種下列類型的化合物:
其中σ,R5,R6,Rs及R9為氯,R7為甲基且R1 , R2, R3及R4皆係如表1所述。 表96涵蓋262種下列類型t巧化合物:
其中G及R5,R8及R9為氫,R6及R7為甲基且R1,R2, R3及R4皆係如表1所述。 表97涵蓋262種下列類型的化合物:
其中 G,R5,R6,R7,R8 及 R9 皆為氯,且 R1,R2,R3 185 201014819 及R4皆係如表1所述。 表98涵蓋262種下列類型的化合物:
R2 R3
其中G,R5,R6,R8及R9為氫,R7為甲基且R1,R2, R3及R4皆係如表1所述。 表99涵蓋262種下列類型的化合物:
R2 R3 〇 其中G及R5,R8及R9為氫,R6及R7為曱基且R1 ’ R2, R3及R4皆係如表1所述。 表100涵蓋262種下列類型的化合物: 186 201014819
R2 ,且 Ri,R2,R3 其中σ,R5,R6,R7,Rs及R9皆為氯 及R4皆係如表1所述。 © 表101涵蓋262種下列類型的化合物:
曱基且R1,R2, 其中G,R5,R6,R8及R9為氫,R7為 R3及R4皆係如表1所述。 © 表102涵蓋262種下列類型的化合物:
其中G及R5,R8及R9為氫,R6及R7為 R3及R4皆係如表1所述。 曱基且R1,R2, 187 201014819 生物實施例
實施例A 將各種試驗物種的種子播種在罐子内的標準土壤中。 在溫室内受控制的條件下栽種1天之後(萌芽前)或在栽 種10天之後(萌穿後)’將植物以在0.6毫升丙酮及含有 10.6%Emulsogen EL (登錄號碼 61791-12-6) 、42·2%Ν-甲 基吡咯啶酮、42.2 %二伸丙甘醇單甲醚(登錄號碼 34590-94-8 )及 0·2%Χ-77 (登錄號碼 11097-66-8)之 45 毫 升調配溶液中的技術級活性成分之調配物所衍生之水性喷 霧溶液喷霧。接著使試驗植物在適宜的條件下在溫室中生 長,直到經萌芽後之後14或15天及經萌芽前19或20天 為止,評估試驗(100=對植物完全損害;〇=對植物沒有任 何損害)。 試驗植物: 大穗看麥娘(Alopecurusmyosuroides) (ALOMY)、 燕麥草(Avena fatua ) ( AVEFA )、黑麥草(Lolium perenne ) (LOLPE )、大狗尾草(Setaria faberi ) ( SETFA )、雞窩 草(Digitaria sanguinalis ) ( DIGSA)、稗草(Echinochloa crus-galli ) ( ECHCG ) 萌芽前活性 化合物 編號 施予率 公克/ 公頃 ALOMY AVEFA LOLPE SETFA DIGSA ECHCG τι 500 100 90 100 70 100 80 Τ2 500 70 10 90 70 80 70 201014819 萌芽粵活性 化合物 編號 施予率 公克/ 公頃 ALOMY AVEFA LOLPE SETFA DIGSA ECHCG T1 125 100 90 100 70 100 100 T2 125 80 40 20 100 100 100 T4 250 100 90 100 90 90 100 T5 250 100 80 100 30 50 80 T8 250 100 90 100 100 80 100 P5 250 100 100 100 80 70 100
實施例B 將各種試驗物種的種子播種在罐子内的標準土壤中。 在溫室内受控制的條件下(在白天/夜晚的24°C / 16^ 下;14小時曰照;65%濕度)栽種1天之後(萌芽前)或 在栽種8天之後(萌芽後),將植物以在含有0.5% Tween (聚氧乙烯山梨醇酐單月桂酸酯,CAS RN 9005-64-5 ) % 丙酮/水(5 0 : 5 0 )溶液中的技術級活性成分之調配物所 衍生之水性喷霧溶液喷霧。 接著使試驗植物在溫室内受控制的條件下(在白天/ 夜晚的24°C / 16°C下;14小時日照;65%濕度)在溫室中 生長及每天澆水兩次。在經萌芽前及後1 3天之後,評估# 驗(100 =對植物完全損害;0 =對植物沒有任何損害)。 試驗植物: 黑麥草(Lolium perenne) ( LOLPE )、大穂看麥娘 189 201014819 (Alopecurus myosuroides) ( ALOMY )、稗草(Echinochloa crus-galli) (ECHCG)、燕麥草(Avenafatua) (AVEFA) 萌芽前活性
化合物編號 施予率 公克/ 公頃 LOLPE ALOMY ECHCG AVEFA T3 250 60 50 20 50 Τ4 250 100 100 100 90 Τ5 250 100 100 100 80 Τ7 250 80 70 100 50 Τ8 250 100 100 100 100 T9 250 60 20 20 0 Τ10 250 90 70 70 40 ΤΙ 1 250 70 30 20 0 Τ12 250 100 100 100 100 Τ13 250 30 30 10 0 Τ14 250 100 100 100 100 Τ15 250 100 70 100 100 Τ16 250 100 100 100 80 Τ17 250 100 100 100 100 Τ18 250 100 100 100 70 Τ21 250 100 100 90 70 Τ22 250 100 100 100 90 Τ23 250 100 100 100 100 190 201014819
T24 250 100 100 100 90 T26 250 100 70 100 60 T27 250 100 90 80 60 T29 250 100 70 90 50 T30 250 90 60 80 30 T31 250 90 80 80 90 T32 250 100 70 100 90 T33 250 90 60 90 50 T34 250 90 70 100 70 T35 250 70 30 40 10 T36 250 90 90 100 90 T37 250 100 10 100 90 T38 250 70 90 100 40 T3 9 250 100 100 100 100 T40 250 100 100 100 80 T41 250 90 70 100 90 T42 250 0 0 20 0 T43 250 100 80 100 100 T44 250 100 90 60 20 T46 250 10 50 10 10 T47 250 60 20 40 50 T48 250 90 90 100 90 T50 250 100 100 100 100 T51 250 100 80 80 90 191 201014819 T52 250 100 100 80 80 T53 250 40 30 0 0 T54 250 100 80 100 50 T55 250 100 80 90 60 T58 250 100 90 100 90 T59 250 100 90 100 90 T60 250 10 10 0 0 T61 250 90 70 90 80 T62 250 100 80 100 70 T63 250 100 70 100 90 T64 250 100 50 100 90 T65 250 80 70 100 80 T66 250 80 90 100 80 T67 250 100 90 100 90 T68 250 90 30 50 40 T69 250 10 0 20 10 T70 250 70 20 60 70 T71 250 30 20 10 20 T72 250 60 30 80 20 T73 250 80 40 80 80 T74 250 30 30 50 20 T75 250 80 30 70 70 T76 250 60 30 60 20 T77 250 0 0 0 0
192 201014819
T78 250 30 20 30 0 T79 250 90 60 60 20 T80 250 100 70 70 70 T81 250 80 80 60 80 T82 250 90 50 60 50 T83 250 90 60 90 70 T84 250 90 50 60 50 T85 250 60 60 30 20 T86 250 100 60 50 30 T87 250 100 90 60 90 T8 8 250 100 90 80 90 T89 250 70 50 60 10 T90 250 60 40 50 60 T91 250 70 20 60 40 T92 250 30 30 40 10 T93 250 90 60 90 60 T94 250 90 90 80 90 T95 250 100 90 60 90 T96 250 60 20 20 10 T97 250 70 30 60 30 T98 250 90 70 90 80 T99 250 60 20 60 30 T100 250 90 60 70 60 T101 250 50 20 50 30 193 201014819
T102 250 70 50 50 30 T103 250 30 30 10 20 T104 250 70 60 90 60 T105 250 60 20 40 30 T106 250 20 20 20 30 T107 250 70 80 70 60 T108 250 50 10 60 40 T109 250 0 0 0 0 ΤΙ 10 250 50 30 70 30 Till 250 90 40 80 40 ΤΙ 12 250 50 40 30 20 ΤΙ 13 250 70 60 90 70 ΤΙ 14 250 40 50 60 20 ΤΙ 18 250 40 40 30 20 ΤΙ 19 250 80 40 100 30 Τ120 250 20 30 30 10 Τ121 250 80 30 90 60 Τ122 250 50 20 70 20 Τ123 250 60 60 60 60 Τ124 250 20 20 30 10 Τ126 250 60 30 50 40 Τ128 250 50 70 60 40 Τ130 250 100 70 30 10 Τ131 250 90 70 100 70 194 201014819
T132 250 70 20 90 70 T135 250 40 0 60 30 T138 250 90 80 90 70 T139 250 80 70 90 60 T140 250 70 60 90 50 T141 250 80 80 80 80 T142 250 70 90 90 80 T143 250 100 80 100 50 T144 250 70 80 90 70 T145 250 50 60 20 30 T146 250 90 70 70 50 T147 250 30 50 40 10 T148 250 50 70 30 40 T149 250 20 30 30 10 T15 1 250 30 20 40 10 T156 250 100 80 100 70 T157 250 10 10 40 0 T158 250 90 80 100 70 T159 250 70 50 100 30 T160 250 90 30 70 40 T161 250 90 30 100 60 T162 250 70 40 50 50 T163 250 80 50 60 60 P5 250 100 100 100 80 195 201014819 P7 250 100 100 100 90 P9 250 40 30 20 0 PI 1 250 100 100 100 100 P13 250 100 100 100 90 P14 250 100 100 100 80 P15 250 100 100 100 90 P16 250 100 100 100 90 P17 250 100 100 90 90 P18 250 100 100 90 80 P20 250 100 100 80 90 P23 250 100 100 100 80 P24 250 100 100 90 90 P25 250 90 100 90 80 P26 250 100 100 90 80 P27 250 100 100 80 80 P28 250 100 70 20 30 P29 250 90 50 0 20 P30 250 100 100 80 90 P31 250 100 100 100 90 P34 250 140 90 100 90 P37 250 100 100 70 70 P42 250 40 30 30 0 P43 250 100 100 100 100 P44 250 100 100 100 90 196 201014819
P45 250 100 100 100 100 P46 250 90 70 100 60 P47 250 60 30 60 50 P48 250 80 70 40 60 P49 250 100 80 100 60 P50 250 100 100 100 100 P51 250 100 100 100 100 P53 250 100 60 90 70 P54 250 100 80 100 70 P55 250 100 100 100 90 P56 250 100 100 100 90 P57 250 60 50 30 70 P58 250 80 70 80 70 P59 250 80 50 70 30 P60 250 80 30 50 0 P61 250 90 50 80 30 P63 250 70 50 70 40 P64 250 80 70 80 70 P65 250 90 60 80 60 P67 250 100 80 90 90 P68 250 100 90 100 90 P71 250 100 90 100 100 197 201014819 萌芽後活性
化合物編號 施予率 公克/ 公頃 LOLPE ALOMY ECHCG AVEFA T3 250 70 40 70 70 T4 250 100 100 100 100 T5 250 100 100 100 90 T6 250 10 20 10 0 T7 250 80 100 90 90 T8 250 100 100 100 100 T9 250 80 60 80 30 T10 250 70 70 80 80 T1 1 250 50 60 70 30 T12 250 100 100 100 100 T13 250 30 10 40 0 T14 250 100 100 100 100 T15 250 100 70 100 100 T16 250 100 100 100 100 T17 250 100 90 100 100 T18 250 100 80 90 70 T21 250 90 90 80 90 T22 250 100 90 100 100 T23 250 100 90 100 100 T24 250 100 90 100 100 198 201014819
T26 250 80 60 60 70 T27 250 80 70 80 70 T29 250 90 70 80 60 T30 250 80 80 80 70 T31 250 70 90 80 90 T32 250 90 90 90 90 T33 250 60 60 60 70 T34 250 90 90 100 100 T35 250 70 70 70 60 T36 250 80 80 90 90 T37 250 100 90 100 100 T38 250 100 100 100 100 T39 250 100 90 100 100 T40 250 100 80 100 90 T41 250 100 100 100 100 T42 250 20 0 30 0 T43 250 100 90 80 90 T44 250 70 60 80 40 T46 250 40 60 60 50 T47 250 30 30 60 50 T48 250 70 90 100 90 T50 250 100 100 100 100 T51 250 60 70 70 80 T52 250 90 90 100 80 199 201014819 T54 250 70 80 80 80 T55 250 60 70 70 50 T58 250 90 100 100 90 T59 250 100 90 90 100 T60 250 20 30 10 10 T61 250 90 90 100 100 T62 250 90 90 100 100 T63 250 90 90 90 100 T64 250 90 90 100 100 T65 250 90 90 100 100 T66 250 60 90 100 90 T67 250 100 90 100 100 T68 250 90 60 90 90 T69 250 30 30 20 30 T70 250 80 70 80 100 T71 250 40 30 70 80 T72 250 80 50 90 80 T73 250 80 90 90 100 T74 250 40 70 100 90 T75 250 100 90 90 100 T76 250 40 90 90 100 T77 250 40 30 20 40 T78 250 50 40 70 40 T79 250 60 60 70 80 200 201014819
T80 250 90 90 80 100 T81 250 90 90 80 100 T82 250 90 90 80 100 T83 250 90 80 70 100 T84 250 100 90 90 100 T85 250 90 90 80 90 TB6 250 70 40 80 80 T87 250 90 70 70 90 T88 250 90 90 90 100 T89 250 40 30 40 20 T90 250 80 70 80 100 T91 250 50 40 50 90 T92 250 20 30 40 60 T93 250 70 60 60 70 T94 250 90 100 90 100 T95 250 100 90 70 100 T96 250 60 60 40 40 T97 250 60 70 80 70 T98 250 100 100 90 100 T99 250 50 70 90 90 T100 250 80 90 60 90 T101 250 40 40 20 40 T102 250 80 90 40 90 T103 250 50 50 30 60 201 201014819 T104 250 80 70 70 90 T105 250 50 30 30 40 T106 250 30 40 30 10 T107 250 90 70 60 90 T108 250 70 70 40 70 ΤΙ 10 250 50 30 40 80 Till 250 80 80 70 90 ΤΙ 12 250 30 40 30 30 ΤΙ 13 250 100 90 70 100 ΤΙ 14 250 50 40 30 40 ΤΙ 16 250 90 60 50 90 Τ118 250 30 60 40 80 ΤΙ 19 250 90 90 90 80 Τ120 250 30 30 10 20 Τ121 250 90 30 80 100 Τ122 250 80 60 70 30 Τ123 250 70 80 60 90 Τ124 250 20 30 20 30 Τ126 250 70 50 60 70 Τ127 250 20 20 20 10 Τ128 250 50 40 50 90 Τ130 250 90 60 60 70 Τ131 250 100 90 90 90 Τ132 250 70 70 100 80
202 201014819
T133 250 0 20 90 30 T135 250 70 80 90 80 T136 250 30 50 60 70 T138 250 90 90 70 90 T139 250 90 90 100 90 T140 250 90 90 90 60 T141 250 70 80 60 90 T142 250 70 90 60 90 T143 250 60 60 60 80 T144 250 80 80 80 90 T145 250 40 60 30 50 T146 250 80 80 70 90 T147 250 40 60 50 70 T148 250 70 80 60 100 T149 250 40 30 20 40 T151 250 20 30 40 10 T152 250 30 20 10 10 T153 250 20 10 10 20 T156 250 100 90 70 90 T157 250 30 30 60 50 T158 250 100 100 100 100 T159 250 100 90 100 90 T160 250 100 40 70 60 T161 250 100 70 90 90 203 201014819 T162 250 90 60 70 80 T163 250 100 90 90 100 P4 250 30 60 20 40 P5 250 100 100 100 90 P7 250 100 100 90 80 P9 250 40 30 50 10 PI 1 250 100 90 100 90 P13 250 100 90 100 90 P14 250 100 90 90 90 P15 250 100 100 100 90 P16 250 100 100 100 100 P17 250 100 100 100 90 P18 250 100 90 90 90 P20 250 100 100 100 90 P23 250 100 90 90 90 P24 250 100 90 90 90 P25 250 100 90 100 90 P26 250 100 100 100 90 P27 250 1 00 80 90 80 P28 250 100 70 60 70 P29 250 100 80 30 70 P30 250 100 100 90 100 P31 250 100 90 100 90 P34 250 100 80 60 90
204 201014819
P37 250 90 90 90 90 P42 250 40 60 70 70 P43 250 100 100 100 90 P44 250 100 100 100 100 P45 250 100 100 90 100 P46 250 80 90 70 90 P47 250 60 70 50 60 P48 250 90 90 90 100 P49 250 100 80 100 90 P50 250 100 100 100 100 P51 250 100 100 100 100 P53 250 20 60 70 40 P54 250 40 70 80 50 P55 250 100 90 100 100 P56 250 100 90 90 100 P57 250 60 80 70 80 P58 250 90 90 70 90 P59 250 80 90 70 80 P60 250 70 80 40 80 P61 250 90 90 90 90 P62 250 80 70 70 70 P63 250 80 90 70 90 P64 250 90 100 90 100 P65 250 90 90 90 90 205 201014819 P67 250 100 100 100 100 P68 250 100 90 100 90 j P69 250 40 0 80 20 P71 250 100 100 100 90 實施例c
將冬小麥物種’’Hereward”的種子播種在罐子内的標準 土壤中。在溫室内受控制的條件下(在白天/夜晚的24。〇 / 16°C下;14小時曰照;65%濕度)栽種8天之後,將植 物以在含有0.5% Tween 20 (聚氧乙烯山梨醇酐單月桂酸 S曰,CAS RN 9005-64-5 )的丙綱/水(5〇: 50)溶液中的 技術級活性成分之調配物所衍生之水性喷霧溶液喷霧。
在溫至測試之前,冬小麥物種,’Hereward”的種子以〇.5 克/公斤乾燥種子的施予率經縠類除草劑安全劑解毒喹 (cloquintocet-methyl )之可濕潤粉末調配物處理。在施用 試驗化合物前8天將一個種子播種在每個15吋塑膠盆中之 砂壤土内1公分深度,且被澆水及在溫室内受控制的條件 下(在白天/夜晚的24°C / 16。(:下;14小時日照;65%濕 度)栽種。將植物以在含有0.5% Tween 20 (聚氧乙缔山架 醇肝單月桂酸酯,CAS RN 9005-64-5 )的丙網/水(5〇 5〇 )溶液中的技術級活性成分之調配物所衍生之水性嘴霧 溶液作萌芽後喷霧。 接著使試驗植物在溫室内受控制的條件下(在白天 65%濕度)在溫室中 夜晚的24°C / 16°C下;14小時日照; 206 201014819 生長及每天澆水兩次。在經萌芽前及後13天之後,評估試 ' 驗(1〇〇=對植物完全損害;0=對植物沒有任何損害)。
化合物編號 施予率 公克/ 公頃 冬小麥 (Hereward) 冬小麥(Hereward) +解毒喹 T4 250 70 40 T5 250 80 20 T8 250 90 80 T10 250 60 20 T12 250 70 60 T14 250 80 60 T16 250 80 20 T17 250 70 50 T22 250 80 70 T37 250 80 70 T39 250 80 70 T40 250 60 10 T41 250 90 80 T62 250 80 70 T64 250 80 70 T66 250 50 20 T67 250 70 30 T75 250 60 50 207 201014819 T84 250 70 60 T88 250 70 50 T98 250 90 60 P5 250 60 30 P7 250 70 0 P1 1 250 80 70 P13 250 70 10 P16 250 70 0 P17 250 70 0 P20 250 40 0 P43 250 50 40 P44 250 70 40 P56 250 90 60 【圖式簡單說明】 無 【主要元件符號說明】
Claims (1)
- 201014819 • 七、申請專利範圍: - 1. 一種式I化合物α) 其中 © R1係為氫,甲基,乙基,正兩基,異丙基,鹵曱基, 鹵乙基,齒素,乙烯基,乙炔基,甲氧基,乙氧基,鹵甲 氧基’齒乙氧基,環丙基或幽環丙基, R及R3獨立地為氫、鹵素、Ci-Cg烧基、C〗-C6鹵烧基、 Ci-C6烧氧基、鹵烧氧基、C2-C6稀基、〇2-C6鹵稀基、 C2-C6快基、C2-C6鹵块基、C3-C6嫦氧基、C3-C6鹵稀氧基、 C3-C6炔氧基、c3-C6環烷基、CrCe烷硫基、Ct-C6烷基亞 磺醯基、烷基磺醯基、Cl-C6烷氧基磺醯基、Ci-Ce鹵 Ο 烷氧基磺醯基、氰基、硝基、苯基、經CVC4烷基、(VC3 鹵烷基、CU-C3烷氧基、Cl_c3鹵烷氧基、氰基、硝基、鹵 素、CrC3烧硫基、Cl_c3烷基亞磺醯基或CrCs烷基磺醯基 取代的苯基’或雜芳基或經Cl_c4烷基、CrCs鹵烷基 烷氧基、Ci-C3鹵烷氧基、氰基、硝基、鹵素、Ci-Cs烷硫 基、C「C3烧基亞磺醯基或Ci_C3烷基磺酿基取代的雜芳基, r4為氯、Cl_C6烷基、c〗-C6鹵烷基、C丨-c6烷氧基、C丨·c6 齒嫁氧基、c2-c6烯基、c2-c6由烯基、c2_c6块基、c3_c6 209 201014819 烯氧基、c3-c6鹵烯氧基、C3-C6炔氧基、C3-C6環烷基' (VC6 * 烷硫基、c!-c6烷基亞磺醯基、CrCe烷基磺醯基、(^-(:6烷 · 氧基磺醯基、C^-Ca鹵烷氧基磺醯基或氱基, R5、R6 ' R7、R8及R9獨立地為氫、函素、CrQ烷基、 Ci_C6 ώ炫基、Ci-Ce炫*氧基、Ci-Ce鹵烧氧基、C2-C6稀基、 C2-C6鹵烯基、C2-C6炔基' c3-c6烯氧基、c3-c6鹵烯氧基、 C3-C6快氧基、C3-C6環烧基、Ci-Ce烧硫基、Ci-C6境基亞 磺醢基、烷基磺醯基、鹵烷基磺醯基、烷 氧基磺醯基、CrQ鹵烷氧基磺醯基、氰基、硝基、苯基、 ◎ 經CrG烷基、CVC3鹵烷基、CVC3烷氧基、(ν〇3鹵烷氧 基 '氰基、硝基、鹵素、CVC3烷硫基' (VC3烷基亞確醯 基或CrC3烷基磺醢基取代的苯基,或雜芳基或經烧 基、CVC3鹵烷基、C「C3烷氧基、(VC3鹵烷氧基、氰基、 石肖基、鹵素、C1-C3烧硫基、CVC3烧基亞續醯基、Ci-C^烧 基磺醯基取代的雜芳基,或苯甲基或經CrCU烷基、 鹵烧基、C1-C3烧氧基、Ci-C:3鹵烧氧基、氰基、硝基、齒 素、CVC3烷硫基、CVC3烷基亞磺醯基或CVC3烷基確醯基 〇 取代的苯甲基,或Cs-C6環烷基(^-Cs烷基,其中環或鏈亞 甲基團視需要被氧原子或硫原子置換,或 R6與R7 ’或R8與R9 —起與其所連接的碳原子形成視 需要取代的3至8員環,其視需要包含氧原子、硫原子或 氮原子,或 R5與R6 —起形成鍵, Q為包含至少一個選自〇、N及S雜原子的C3-C8飽和 210 201014819 或單不飽和雜環基,其未經取代或經為殘基的式=〇、=N-R10 或cvq烷基、Ci-c4齒烷基、Ci_C4烷氧基Ci_C2烷基、C3_C6 環烷基、苯基、經c^c:4烷基、Ci_C3鹵烷基、Cl_C3燒氧基、 CVC3鹵烷氧基、氰基、硝基 '鹵素、Ci_C3烷硫基、Ci_C3 烷基亞磺醯基或c〗-c:3烷基磺醯基取代的苯基,其中Ri〇為 CVC6烧基、CVC6 _烧基、c3_c7環烧基、Ci_c6烧氧基、 C「C6鹵烷氧基、CrC6烷基亞磺醯基、Cl-c6烷基磺醯基、 CVC6鹵烧基幾基、CVC6烷氧基羰基、Cl-C6烷基胺基羰基、 ® C2_C8二烧基胺基幾基、CVC6鹵烷基亞磺醯基或CVC6鹵烷 基磺醯基, m為1、2或3, 其中當m為2或3時,R6或R7可具有不同意義,及 G為氫或農業上可接受之金屬、鈒、銨、或潛伏化基團。 2. 根據申請專利範圍第1項之化合物,其中Ri為甲基、 乙基或甲氧基。 3. 根據申請專利範圍第1項之化合物,其中R2及R3獨 © 立地為氫、鹵素、CVC6烷基、CVC6鹵烷基、C2_C6烯基、 c2-c6炔基、c2-c6鹵炔基、苯基或經CVC4烷基、c〗-c3鹵 烧基、氰基、硝基或Crq烷基磺醯基取代之苯基。 4. 根據申請專利範圍第1項之化合物,其中R2及R3獨 立地為噻吩基、經¢^-(^烷基、C^-Cs鹵烷基烷氧基、 cvc3鹵烷氧基、氰基、确基、鹵素、Cl_c3烷硫基、Cl_c3 炫基亞磺醯基或Ct-Cs烷基磺醯基取代的噻吩基,呋喃基、 經CVC3烷基、CVC3鹵烷基' Ci-Cs烷氧基、(VC3鹵烷氧 211 201014819 基、氰基、硝基、鹵素、CVC3烷硫基、CrCs烷基亞磺醯 -基或C1-C3烧基續酿基取代的β夫喃基,„比。坐基,經-基、CVC3齒烧基、CVC3烷氧基、CVC3鹵烷氧基、氰基、 硝基 '鹵素、CVC3烷硫基、CVC3烷基亞磺醯基或C「C3 烷基磺醯基取代的吡唑基’噻唑基,經Cl_c3烧基、CrCs 鹵烧基、CVC3烷氧基、C^C:3鹵烷氧基、氰基、硝基、鹵 素、C1-C3烷硫基、C^-C3烷基亞磺醯基或Cl-C3烷基磺酿基 取代的噻唑基’噁唑基,經Ci-C3烷基、CrCs鹵烷基、 烷氧基、CrC3鹵烷氧基、氰基、硝基、鹵素、Cl_c3烷硫 ® 基、Ci-C3烷基亞磺醯基或Ci-C^烷基確醯基取代的噁唑 基,異噻唑基,經(VC3烷基、CVC3鹵烷基、CVC3烷氧基、 Ci-C3鹵烷氧基、氰基、硝基、鹵素、Cl-C3烷硫基' Ci-C3 烧基亞績醯基或CkC3娱;基續醯基取代的異嘆。坐基,異》惡喷 基,經cvc3烷基、CVC3鹵烷基、Ci-Cs烷氧基、(VC3鹵 燒氧基、氟基、硝基、鹵素、CVC3烧硫基、CKC3院基亞 磺醢基或CrCs烷基磺醯基取代的異噁唑基,三唑基,經 (VC3烷基、CVC3鹵烷基、CVC3烷氧基、CVC3鹵烷氧基、 © 氰基、硝基、鹵素、CkCs烷硫基、烷基亞磺醯基或 c 1-C3烧基墙醮基取代的三唾基,噁二嗤基,經ci -C3烧基、 CVC3鹵烷基、CVC3烷氧基、(VC3鹵烷氧基、氰基、硝基、 鹵素、C^-Cs烷硫基' Ci-Cs烷基亞磺醯基或烷基磺醯 基取代的噁二唑基,噻二唑基,經烷基、鹵烷 基、C〗-C3烷氧基、CVC3鹵烷氧基、氰基、硝基、鹵素、 Ci-C3烷硫基、Ci-Cs烷基亞磺醯基或C^-Cs烷基磺醯基取代 212 201014819 的嗟二唾基,四坐基,經撰;基、C1-C3鹵炫•基、C丨-C3 烷氧基、鹵烷氧基、氰基、硝基、鹵素、Ci-C3烷硫 基、CrG烷基亞磺醯基或C^-Cs烷基磺醢基取代的四唑 基,吡啶基,經CVC3烷基、c丨-C3鹵炫基、Cl-C3烷氧基、 CVC3鹵烷氧基、氰基、硝基、鹵素、CVC3烷硫基、CVC3烷基亞磺醯基或Ci-C^烷基磺醯基取代的吡啶基’嘧啶基, 經CVC3烷基、(VC3鹵烷基、Cl-C3烷氧基、Ci-q鹵烷氧 基、氰基、石肖基、鹵素、院硫基、C1-C3烧基亞續醢 基或Ci-C3烷基續醯基取代的嘧啶基,嗒嗪基,經ci-c3烷 基、cvc3鹵烧基、cvc3烷氧基、Cl-C3鹵烷氧基、氰基、 硝基、鹵素、C1-C3烷硫基、Ci_c3烷基亞磺醯基或Ci_c3 烷基磺醢基取代的嗒嗪基,吡嗪基,經C1_C3烷基、C1_C3 鹵烷基、CVC3烷氧基、CVc3鹵烷氧基、氰基、硝基、鹵 素、CrC3烷硫基、CrC3烷基亞磺醯基或€ι·(:3烷基磺醯基 取代的吡嗪基,二嗪基,經C^-C3烷基、鹵烷基、Ci-Cs氦基、硝基、鹵素、Ci-Cs烷硫 烷氧基、Ci-C^鹵烷氧基 基、烷基亞磺醯基或Ci -C3烷基磺酿基取代的三嗪基。 鹵乙基、鹵素、 213 201014819 8. 根據申請專利範圍第1項之化合物,其中r6以及r7 獨立地為氫、鹵素、C1-C6烧基、C1-C6齒炫•基、Ci-C6烧乳 基或c「c6鹵烷氧基。 9. 根據申請專利範圍第1項之化合物,其中r8以及r9 獨立地為氯、鹵素、Ci_Ce炫•基、Ci-Cg画烧基、C!-C6烧氧 基或鹵烷氧基。 10. 根據申請專利範圍第1項之化合物’其中Q為下式 者214 201014819215 201014819其中 R為氮、鹵素、Ci_C6^基、Ci_C6 _烧基、C「C6烧氧 基、CVC6鹵烷氧基、c2-c6烯基、c2-c6鹵烯基、c2-c6炔 基、c2-c6鹵炔基、c3-c6烯氧基、c3-c6鹵烯氧基、C3-C6 炔氧基、C3-C6環烷基、Ci-Ce烷硫基、Ci-C6烷基亞磺醯基、 CVC6烷基績醯基、C「c6烷氧基磧醯基、C「C6鹵烧氧基確 216 201014819 醯基、氰基、确基、苯基、經C1-C4炫基、.C1-C3鹵烧基、 • (VC3炫氧基、Ci-C^鹵烧氧基、氰基、硝基、鹵素、CVC3 烷硫基、CrCs烷基亞磺醯基或Ci-Cs烷基磺醯基取代的苯 基,或雜芳基或經CrG烷基、CrCs鹵烷基、(^-(:3烷氧基、 CVC3鹵烷氧基、氰基、硝基、鹵素、CVC3烷硫基、(VC3 烷基亞磺醯基或Ci-Cs烷基磺醯基取代的雜芳基, R’為氳、CVC6烷基、CVC6 _烷基、C3-C7環烷基、(VC6 烷氧基、C^-Ce鹵烷氧基、CrCe烷基亞磺醯基、(^-匕烷基 Ο 磺醯基、CVC6烷基羰基、CVC6鹵烷基羰基、CVC6烷氧基 羰基、<^-(:6烷基胺基羰基、C2-C8二烷基胺基羰基、c6-c10 芳基磺醯基、c6-c1G芳基羰基、c6-c1()芳基胺基羰基、c7-c16 芳基烷基胺基羰基、Ci-C^雜芳基磺醯基、C^-Cs雜芳基羰 基、Crq雜芳基胺基羰基、(:2-(:15雜芳基烷基胺基羰基, R”為氫、CVC6烷基、CVC6鹵烷基、C3-C7環烷基'CVC6 烷氧基、CrCe鹵烷氧基、烷基亞磺醯基、(^-(:6烷基 績醢基、CVC6烷基羰基、CVC6鹵烷基羰基、Ci-Q烷氧基 ® 幾基、c「c6烷基胺基羰基、C2-C8二烷基胺基羰基、C!-C6 鹵烧基亞績醯基或心-匕鹵燒基續醯基, η為〇、1、2、3或4,以及 Α代表連接至_CR6R7-部分的位置。 u. 一種製備根據前述申請專利範圍第1項所述之化合 物之方法。 12.—種式(B)化合物, 217 201014819其R1至R9係定義於申請專利範圍第1項且R,,’為氫或 烷基。 13.—種式(C)化合物’其至R9係定義於申請專利範圍第1項且R’,,為氫或 烷基。14. 一種除草組合物,其除了包含調配物佐劑之外,包 含除草有效量之式I化合物。 15. —種控制有用植物之作物中的禾草及雜草之方法, 其包含將除草有效量之式!化合物,或含有該化合物之組合 物施予植物或其所在地。 八、圖式: 無 218
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-
2008
- 2008-07-03 GB GB0812310A patent/GB0812310D0/en not_active Ceased
-
2009
- 2009-07-01 AU AU2009265680A patent/AU2009265680B2/en active Active
- 2009-07-01 NZ NZ590055A patent/NZ590055A/en not_active IP Right Cessation
- 2009-07-01 CN CN2009801294512A patent/CN102112439B/zh active Active
- 2009-07-01 HU HUE09772473A patent/HUE028084T2/en unknown
- 2009-07-01 ES ES09772473.6T patent/ES2553418T3/es active Active
- 2009-07-01 PL PL09772473T patent/PL2313370T3/pl unknown
- 2009-07-01 AR ARP090102459 patent/AR072459A1/es active IP Right Grant
- 2009-07-01 KR KR20117002737A patent/KR20110031221A/ko not_active Application Discontinuation
- 2009-07-01 BR BRPI0914107-3A patent/BRPI0914107B1/pt active IP Right Grant
- 2009-07-01 JP JP2011515449A patent/JP5524959B2/ja not_active Expired - Fee Related
- 2009-07-01 CA CA2729724A patent/CA2729724C/en active Active
- 2009-07-01 EA EA201170132A patent/EA021735B1/ru not_active IP Right Cessation
- 2009-07-01 DK DK09772473.6T patent/DK2313370T3/en active
- 2009-07-01 US US13/002,343 patent/US9096560B2/en active Active
- 2009-07-01 MX MX2010014311A patent/MX2010014311A/es not_active Application Discontinuation
- 2009-07-01 UA UAA201101185A patent/UA103625C2/ru unknown
- 2009-07-01 WO PCT/EP2009/058250 patent/WO2010000773A1/en active Application Filing
- 2009-07-01 EP EP09772473.6A patent/EP2313370B1/en active Active
- 2009-07-02 TW TW98122383A patent/TW201014819A/zh unknown
- 2009-07-02 CL CL2009001513A patent/CL2009001513A1/es unknown
-
2010
- 2010-12-22 ZA ZA2010/09220A patent/ZA201009220B/en unknown
- 2010-12-23 IL IL210202A patent/IL210202A0/en unknown
-
2011
- 2011-01-18 CO CO11004798A patent/CO6341609A2/es not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
MX2010014311A (es) | 2011-02-15 |
KR20110031221A (ko) | 2011-03-24 |
IL210202A0 (en) | 2011-03-31 |
CN102112439A (zh) | 2011-06-29 |
PL2313370T3 (pl) | 2016-01-29 |
ZA201009220B (en) | 2011-09-28 |
HUE028084T2 (en) | 2016-11-28 |
CA2729724C (en) | 2016-04-19 |
US9096560B2 (en) | 2015-08-04 |
NZ590055A (en) | 2012-06-29 |
CO6341609A2 (es) | 2011-11-21 |
JP5524959B2 (ja) | 2014-06-18 |
WO2010000773A1 (en) | 2010-01-07 |
EP2313370A1 (en) | 2011-04-27 |
AU2009265680A1 (en) | 2010-01-07 |
ES2553418T3 (es) | 2015-12-09 |
JP2011526597A (ja) | 2011-10-13 |
CN102112439B (zh) | 2013-07-24 |
EA021735B1 (ru) | 2015-08-31 |
DK2313370T3 (en) | 2015-11-30 |
EA201170132A1 (ru) | 2011-08-30 |
US20110263428A1 (en) | 2011-10-27 |
BRPI0914107B1 (pt) | 2022-01-11 |
AR072459A1 (es) | 2010-09-01 |
UA103625C2 (en) | 2013-11-11 |
BRPI0914107A2 (pt) | 2021-04-27 |
AU2009265680B2 (en) | 2014-05-22 |
EP2313370B1 (en) | 2015-08-19 |
CL2009001513A1 (es) | 2009-10-23 |
CA2729724A1 (en) | 2010-01-07 |
GB0812310D0 (en) | 2008-08-13 |
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