TW202132273A - 唑衍生物及其用途 - Google Patents
唑衍生物及其用途 Download PDFInfo
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- TW202132273A TW202132273A TW109137441A TW109137441A TW202132273A TW 202132273 A TW202132273 A TW 202132273A TW 109137441 A TW109137441 A TW 109137441A TW 109137441 A TW109137441 A TW 109137441A TW 202132273 A TW202132273 A TW 202132273A
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- Prior art keywords
- alkyl
- group
- compound
- amino
- compound represented
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- 150000007980 azole derivatives Chemical class 0.000 title description 10
- -1 C 6 alkane Chemical group 0.000 claims description 751
- 150000001875 compounds Chemical class 0.000 claims description 370
- 150000003839 salts Chemical class 0.000 claims description 111
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 96
- 241000607479 Yersinia pestis Species 0.000 claims description 95
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 239000003795 chemical substances by application Substances 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000000575 pesticide Substances 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 230000000895 acaricidal effect Effects 0.000 claims description 9
- 239000000642 acaricide Substances 0.000 claims description 9
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 9
- 239000002917 insecticide Substances 0.000 claims description 9
- 239000005645 nematicide Substances 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000006798 recombination Effects 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 4
- 238000009395 breeding Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000002420 orchard Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 238000005215 recombination Methods 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 241000209094 Oryza Species 0.000 claims 2
- 239000003905 agrochemical Substances 0.000 claims 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
- 230000000856 effect on pests Effects 0.000 claims 1
- 125000000232 haloalkynyl group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 161
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 68
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 56
- 229910052751 metal Inorganic materials 0.000 description 54
- 239000002184 metal Substances 0.000 description 54
- 239000002904 solvent Substances 0.000 description 47
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 239000002585 base Substances 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 29
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 24
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 24
- 125000000753 cycloalkyl group Chemical group 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 229910052783 alkali metal Inorganic materials 0.000 description 21
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 21
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- 150000001298 alcohols Chemical class 0.000 description 20
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 20
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 19
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 18
- 239000003446 ligand Substances 0.000 description 18
- 239000011734 sodium Substances 0.000 description 18
- 229910052708 sodium Inorganic materials 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 16
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- 238000004821 distillation Methods 0.000 description 15
- 239000011591 potassium Substances 0.000 description 15
- 229910052700 potassium Inorganic materials 0.000 description 15
- 229960003975 potassium Drugs 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 15
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 13
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 13
- 150000008282 halocarbons Chemical class 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 235000011181 potassium carbonates Nutrition 0.000 description 13
- 239000008096 xylene Substances 0.000 description 13
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 12
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 12
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 12
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 12
- 150000002825 nitriles Chemical class 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 239000007800 oxidant agent Substances 0.000 description 12
- 239000002798 polar solvent Substances 0.000 description 12
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 11
- 150000001340 alkali metals Chemical class 0.000 description 11
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 235000015497 potassium bicarbonate Nutrition 0.000 description 11
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 11
- 239000011736 potassium bicarbonate Substances 0.000 description 11
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 11
- 150000003222 pyridines Chemical class 0.000 description 11
- 150000003512 tertiary amines Chemical class 0.000 description 11
- 241000254173 Coleoptera Species 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 description 10
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 10
- 150000008041 alkali metal carbonates Chemical class 0.000 description 10
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
- 229910000024 caesium carbonate Inorganic materials 0.000 description 10
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 10
- 239000000920 calcium hydroxide Substances 0.000 description 10
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 150000004679 hydroxides Chemical class 0.000 description 10
- 150000007529 inorganic bases Chemical class 0.000 description 10
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 10
- 229910052808 lithium carbonate Inorganic materials 0.000 description 10
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 10
- 229910000103 lithium hydride Inorganic materials 0.000 description 10
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 10
- 239000000347 magnesium hydroxide Substances 0.000 description 10
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 10
- 229910052987 metal hydride Inorganic materials 0.000 description 10
- 150000004681 metal hydrides Chemical class 0.000 description 10
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 10
- 229910000105 potassium hydride Inorganic materials 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 239000011775 sodium fluoride Substances 0.000 description 10
- 235000013024 sodium fluoride Nutrition 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 10
- 235000019798 tripotassium phosphate Nutrition 0.000 description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 9
- YJUUZFWMKJBVFJ-UHFFFAOYSA-N 1,3-dimethylimidazolidin-4-one Chemical compound CN1CN(C)C(=O)C1 YJUUZFWMKJBVFJ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- 125000002619 bicyclic group Chemical group 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000010586 diagram Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 8
- 230000000749 insecticidal effect Effects 0.000 description 8
- 229910000000 metal hydroxide Inorganic materials 0.000 description 8
- 150000004692 metal hydroxides Chemical class 0.000 description 8
- 125000003226 pyrazolyl group Chemical group 0.000 description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- 241000254171 Curculionidae Species 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 229910052791 calcium Inorganic materials 0.000 description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 7
- YQFFHPXGRDVLLR-UHFFFAOYSA-N (2,3,4-triphenylphenyl)phosphane Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC=CC=2)C(P)=CC=C1C1=CC=CC=C1 YQFFHPXGRDVLLR-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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Abstract
本發明課題為提供優異的有害生物防治劑。提供一種有害生物防治劑,其特徵在於,作為有效成分而含有式[I]
[式中,R1
係表示:氫原子;氰基;或是未取代或以鹵素原子取代的C1
~C7
醯基;R2
係表示:C1
~C6
烷基等;A3
, A4
, A5
, A6
, A7
, A8
及A9
分別獨立地表示氮原子,或是分別以R3
, R4
, R5
, R6
, R7
, R8
及R9
取代的碳原子;R3
, R4
, R5
, R6
, R7
, R8
及R9
分別獨立地表示:氫原子;鹵素原子;R1 0
係表示氫原子;C1
~C12
烷基;C1
~C6
烷氧基C1
~C6
烷基;C1
~C12
鹵代烷基等;R11
係表示鹵素原子;疊氮基;氰基等]所示的唑衍生物或是其農藥上可允許的鹽。
Description
本發明係關於一種新穎的唑衍生物或是其農業上允許的鹽、以及以含有該衍生物或是其鹽以作為有效成分的有害生物防治劑及製造中間體。
專利文獻1當中記載具有除草活性的N-1(1,3,4-惡二唑-2-基)芳基羧酸醯胺衍生物。然而,專利文獻1當中並沒有關於殺蟲活性之記載。
專利文獻2記載具有除草活性的嘧啶基氧基(硫代)苯衍生物。專利文獻2中所記載的化合物係僅限於:其苯環之第2位由吡唑環取代且第3位由甲磺醯基取代的化合物。此外,專利文獻2當中並沒有關於殺蟲活性之記載。
專利文獻3當中記載具有除草活性的N-(1,3,4-惡二唑-2-基)苯甲醯胺衍生物。專利文獻3中所記載的化合物係僅限於:其苯甲醯胺之第3位由吡唑環取代,而第2位係甲基及氯基,第4位由甲磺醯基取代的化合物。此外,專利文獻3中並沒有關於殺蟲活性之記載。
專利文獻4當中記載一種N-(1,2,5-惡二唑-3-基)苯甲酸醯胺衍生物。專利文獻4中記載的化合物僅限於:其苯甲醯胺之第3位由吡唑取代,而在第2位係甲基及氯基,且甲磺醯基鍵合至第4位的化合物。此外,專利文獻4中並沒有關於殺蟲活性之記載。
專利文獻5當中記載具有除草活性的N-(四唑-5-基)芳基羧酸醯胺衍生物和N-(1,2,4-三唑-5-基)芳基羧酸醯胺衍生物。專利文獻5中記載的化合物僅限於:其苯甲醯胺之第3位由吡唑取代,第2位係甲基及氯基,甲磺醯基鍵合至第4位的化合物。此外,專利文獻5中並沒有關於殺蟲活性之記載。
專利文獻6當中記載具有除草活性的N-(1,2,5-惡二唑-3-基)苯甲醯胺衍生物。專利文獻6中所記載的化合物僅限於:其苯甲醯胺之第3位由吡唑環取代,而第2位係甲基,第4位由甲磺醯基取代的化合物。此外,專利文獻6中並沒有關於殺蟲活性之記載。
專利文獻7當中記載3-環丙基-4-(3-氨基-2-甲基苯甲醯基)吡唑衍生物。專利文獻7中所記載的化合物係僅限於:其作為苯甲醯基上第3位的氨基之一係由吡唑環所取代,而第2位係甲基,第4位由甲磺醯基取代的化合物。此外,專利文獻7中並沒有關於殺蟲活性之記載。
[先前技術文獻]
[專利文獻]
[專利文獻1] 國際公開第2018/177871號
[專利文獻2] 國際公開第2015/089003號
[專利文獻3] 國際公開第2012/126932號
[專利文獻4] 國際公開第2012/123420號
[專利文獻5] 國際公開第2012/028579號
[專利文獻6] 國際公開第2011/035874號
[專利文獻7] 國際公開第2006/061074號
[發明所欲解決問題]
人們對於用在有用作物上的害蟲防治劑,希望其為施用到土壤或樹葉並以低劑量表現出足夠的害蟲防治效果的藥劑。另外,對化學物質的安全性及其對環境的影響的需求日益增加,因而期望開發更安全的害蟲防治劑。此外,近年來,由於長年使用諸如殺蟲劑、殺蟎劑和殺線蟲劑的關係,已經出現了對殺蟲劑具有抗性的有害生物,因此,完全防治有害生物已經變得困難。此外,就使用對人畜具有高毒性的有害生物防治劑上,也存在著對在對於作業者的安全性等方面的問題。
本發明的課題在於,提供一種有害生物防治劑及為了該目的的新穎化合物,其係解決了上述事項當中,傳統的有害生物防治劑所具有的上述問題,並且還具有優異的安全性、防治效果、殘留性等。
[解決問題之手段]
本案發明人為了要開發具有上述優異特性的有害生物防治劑,合成了各種的唑衍生物,並致力研究其生理活性。其結果為,發現到以下述通式[I]所示的唑衍生物(以下稱為本發明之化合物)具有對各種有害生物的優異防治功效,並且進一步持續研究而完成本發明。
也就是說,本發明係關於下述事項。
(1)一種化合物或是其鹽,係表示為:
通式[I]
[式中,
m及n係分別獨立且表示0、1或2的整數,且m及n的總和係在為0~2的整數之範圍內,
R1
係表示:氫原子;氰基;或是未取代或以鹵素原子取代的C1
~C7
醯基;
R2
係表示:C1
~C6
烷基;C1
~C6
烷氧基C1
~C6
烷基;C1
~C6
鹵代烷基;C1
~C6
烷氧基C1
~C6
鹵代烷基;C1
~C6
鹵代烷氧基C1
~C6
烷基;C1
~C6
鹵代烷氧基C1
~C6
鹵代烷基;C3
~C6
環烷基;C3
~C6
鹵代環烷基;C3
~C6
環烷基C1
~C6
烷基;C3
~C6
鹵代環烷基C1
~C6
烷基;氰基C1
~C6
烷基;未取代或以R11
任意取代的C7
~C1 4
芳烷基;或未取代或以R11
任意取代的C6
~C12
雜芳烷基;
A3
, A4
, A5
, A6
, A7
, A8
及A9
分別獨立地表示氮原子,或是分別以R3
, R4
, R5
, R6
, R7
, R8
及R9
取代的碳原子;
R3
, R4
, R5
, R6
, R7
, R8
及R9
分別獨立地表示:氫原子;鹵素原子;疊氮基;氰基;硝基;C1
~C6
烷基、C1
~C6
烷氧基C1
~C6
烷基;C1
~C6
鹵代烷氧基C1
~C6
烷基;氰基C1
~C6
烷基;C1
~C6
鹵代烷基;C3
~C6
環烷基;氰基C3
~C6
環烷基;C3
~C6
鹵代環烷基;C3
~C6
環烷基C1
~C6
烷基;C3
~C6
鹵代環烷基C1
~C6
烷基;C2
~C6
烯基;C2
~C6
鹵代烯基;C2
~C6
炔基;C2
~C6
鹵代炔基;C3
~C6
環烷基C2
~C6
炔基;未取代或以R11
任意取代的雜環基;未取代或以R11
任意取代的C6
~C12
芳基;未取代或以R11
任意取代的C5
~C12
雜芳基;未取代或以R11
任意取代的C7
~C1 4
芳烷基;未取代或以R11
任意取代的C6
~C12
雜芳烷基;羥基;C1
~C6
烷氧基;C1
~C6
鹵代烷氧基;氰基C1
~C6
烷氧基;羥基C1
~C6
烷氧基;C1
~C6
鹵代烷氧基C1
~C6
烷氧基;C1
~C6
烷氧基C1
~C6
鹵代烷氧基;C1
~C6
鹵代烷氧基C1
~C6
鹵代烷氧基;C3
~C6
環烷基氧基;C3
~C6
環烷基C1
~C6
烷氧基;C3
~C6
鹵代環烷基氧基;C3
~C6
鹵代環烷基C1
~C6
烷氧基;C1
~C6
鹵代烷硫基C1
~C6
烷氧基;C1
~C6
鹵代烷基亞磺醯基C1
~C6
烷氧基;C1
~C6
鹵代烷基磺醯基C1
~C6
烷氧基;未取代或以R11
任意取代的C7
~C1 4
芳烷氧基;未取代或以R11
任意取代的C6
~C12
雜芳烷氧基;未取代或以R11
任意取代的C6
~C12
芳氧基;或未取代或以R11
任意取代的C5
~C12
雜芳氧基;硫烷基;五鹵硫烷基;C1
~C6
烷硫基;C1
~C6
烷基亞磺醯基;C1
~C6
烷基磺醯基;C1
~C6
鹵代烷基硫磺基;C1
~C6
鹵代烷基亞磺醯基;C1
~C6
鹵代烷基磺醯基;C3
~C6
環烷基硫基;C3
~C6
環烷基磺醯基;C3
~C6
環烷基磺醯基;C3
~C6
鹵代環烷基硫基;C3
~C6
鹵代環烷基亞磺醯基;C3
~C6
鹵代環烷基磺醯基,C3
~C6
環烷基C1
~C6
烷硫基;C3
~C6
環烷基C1
~C6
烷基亞磺醯基;C3
~C6
環烷基C1
~C6
烷基磺醯基;C3
~C6
鹵代環烷基C1
~C6
烷硫基;C3
~C6
鹵代環烷基C1
~C6
烷基亞磺醯基;C3
~C6
鹵代環烷基C1
~C6
烷基磺醯基;C6
~C12
芳硫基;C6
~C12
芳基亞磺醯基;C6
~C12
芳基磺醯基;C5
~C12
雜芳硫基;C5
~C12
雜芳基亞磺醯基;C5
~C12
雜芳基亞磺醯基;氨基;單(C1
~C6
烷基)氨基;二(C1
~C6
烷基)氨基;C1
~C6
烷基羰基氨基;N-(C1
~C6
烷基羰基)-N-(C1
~C6
烷基)氨基;C1
〜C6
烷氧基羰基氨基;C1
~C6
烷氧基羰基氨基;N-(C1
~C6
烷氧基羰基羰基)-N-(C1
~C6
烷基)氨基;N-(C1
~C6
烷氧基羰基)-N-(C1
~C6
烷基)氨基;氨基羰基氨基;N-(氨基羰基)-N-(C1
~C6
烷基)氨基;N-(單(C1
~C6
烷基)氨基羰基)氨基;N-(單(C1
~C6
烷基)氨基羰基)-N-(C1
~C6
烷基)氨基;N-(二(C1
~C6
烷基)氨基羰基)氨基;N-(二(C1
~C6
烷基)氨基羰基羰基)氨基;N-(二(C1
~C6
烷基)氨基羰基)-N-(C1
~C6
烷基)氨基;N-(二(C1
~C6
烷基)氨基羰基羰基)-N-(C1
~C6
烷基)氨基;氨基(硫代羰基)氨基;N-(二(C1
~C6
烷基)氨基(硫代羰基))氨基;N-(二(C1
~C6
烷基)氨基(硫代羰基))-N-(C1
~C6
烷基)氨基;C1
~C6
烷基磺醯基氨基;C1
~C6
鹵代烷基磺醯基氨基;N-(C1
~C6
烷基磺醯基)-N-(C1
~C6
烷基)氨基;N-(C1
~C6
鹵代烷基磺醯基)-N-(C1
~C6
烷基)氨基;二(C1
~C6
烷基磺醯基)氨基;二(C1
~C6
鹵代烷基磺醯基)氨基;氨基磺醯基氨基;N-(氨基磺醯基)-N-(C1
~C6
烷基)氨基;N-(單(C1
~C6
烷基)氨基磺醯基)氨基;N-(單(C1
~C6
烷基)氨基磺醯基)-N-(C1
~C6
烷基)氨基;N-(二(C1
~C6
烷基)氨基磺醯基)氨基;N-(二(C1
~C6
烷基)氨基磺醯基)-N-(C1
~C6
烷基)氨基;(二(C1
~C6
烷基)亞硫烷基)氨基((di(C1
~C6
alkyl)sulfinylidene)amino);C1
~C7
醯基;C1
~C7
鹵代醯基;羥基亞氨基C1
〜C6
烷基;羥基亞氨基(氨基)C1
〜C7
烷基;C1
〜C6
烷氧基亞氨基C1
〜C6
烷基;C1
〜C6
鹵代烷氧基亞氨基C1
〜C6
烷基;羧基;C1
〜C6
烷氧基羰基;氨基羰基;單(C1
~C6
烷基)氨基羰基;二(C1
~C6
烷基)氨基羰基;單(C1
~C6
鹵代烷基)氨基羰基;單(C3
~C6
環烷基)氨基羰基;(C1
〜C6
烷氧基)(C1
~C6
烷基)氨基羰基;氨基硫代羰基;單(C1
~C6
烷基)氨基硫代羰基;二(C1
~C6
烷基)氨基硫代羰基;或N-(C1
~C6
烷氧基)-N-(C1
~C6
烷基)氨基羰基,且,R3
與R4
、R4
與R5
、或是R5
與R6
係可分別地形成具有將其鍵合的碳原子及3〜6元的碳環或是具有選自氧原子、硫原子、氮原子的1〜4個雜原子的3〜6元的雜環,該碳環及該雜環係可分別以鹵素原子;氰基;硝基;C1
〜C6
烷基;C1
〜C6
烷氧基;C1
〜C6
鹵代烷基;C1
〜C6
鹵代烷氧基;C3
~C6
環烷基;C1
~C6
烷氧基亞氨基C1
~C6
烷基;C1
~C6
鹵代烷氧基亞氨基C1
~C6
烷基;羥基;氧代基;或硫氧基(thioxy)取代,
R1 0
係表示:氫原子;C1
~C12
烷基;C1
~C6
烷氧基C1
~C6
烷基;C1
~C12
鹵代烷基;C1
~C6
烷氧基C1
~C6
鹵代烷基;C1
~C6
鹵代烷氧基C1
~C6
烷基;C1
~C6
鹵代烷氧基C1
~C6
鹵代烷基;C2
~C6
烯基;C2
~C6
鹵代烯基;C2
~C6
炔基;C3
~C6
環烷基C2
~C6
炔基;C2
~C6
鹵代炔基;C3
~C6
環烷基;C3
~C6
鹵代環烷基;C3
~C6
環烷基C1
~C6
烷基;C3
~C6
鹵代環烷基C1
~C6
烷基;C1
~C6
烷硫基C1
~C6
烷基;C1
~C6
烷基亞磺醯基C1
~C6
烷基;C1
~C6
烷基磺醯基C1
~C6
烷基;C1
~C6
鹵代烷硫基C1
~C6
烷基;C1
~C6
鹵代烷基亞磺醯基C1
~C6
烷基;C1
~C6
鹵代烷基磺醯基C1
~C6
烷基;C1
~C6
烷基羰基C1
~C6
烷基;C1
~C6
鹵代烷基羰基C1
~C6
烷基;C1
~C6
烷氧基羰基C1
~C6
烷基;氨基羰基C1
~C6
烷基;單(C1
~C6
烷基)氨基羰基C1
~C6
烷基;單(C3
~C6
環烷基)氨基羰基C1
~C6
烷基;單(C1
~C6
鹵代烷基)氨基羰基C1
~C6
烷基;二(C1
~C6
烷基)氨基羰基C1
~C6
烷基;單(C1
~C6
烷基羰基)氨基C1
~C6
烷基;單(C1
~C6
烷氧基羰基)氨基C1
~C6
烷基;單(C1
~C6
烷基磺醯基)氨基C1
~C6
烷基;單(C1
〜C6
鹵代烷基磺醯基)氨基C1
~C6
烷基;羥基C1
~C6
烷基;羥基亞氨基C1
~C6
烷基;C1
~C6
烷氧基亞氨基C1
~C6
烷基;C1
~C6
鹵代烷氧基亞氨基C1
~C6
烷基;氨基羰基;單(C1
~C6
烷基)氨基羰基;單(C3
~C6
環烷基)氨基羰基;單(C1
~C6
鹵代烷基)氨基羰基;二(C3
~C6
環烷基)氨基羰基; (C1
~C6
鹵代烷基)(單(C1
~C6
鹵代烷基)氨基羰基)氨基羰基;(C1
~C6
鹵代烷基)(C1
~C6
鹵代烷基亞氨基C1
~C6
鹵代烷基)氨基羰基;C1
~C7
醯基;C1
~C7
鹵醯基;未取代或是以R11
任意取代的C6
~C12
芳基羰基;C1
~C6
烷基磺醯基;C1
~C6
鹵代烷基磺醯基;未取代或以R11
任意取代C7
~C1 4
的芳烷基;未取代或以R11
任意取代的C6
~C12
雜芳烷基;未取代或以R11
任意取代的C6
~C12
芳基;或是未取代或以R11
任意取代的C5
~C12
雜芳基,
R11
係表示:鹵素原子;疊氮基;氰基;硝基;C1
~C6
烷基;C1
~C6
鹵代烷基;C1
~C6
烷氧基;C1
~C6
鹵代烷氧基;C3
~C6
環烷基;五鹵硫烷基;C1
~C6
烷硫基;C1
~C6
烷基亞磺醯基;C1
~C6
烷基磺醯基;C1
~C6
鹵代烷硫基;C1
~C6
鹵代烷基亞磺醯基;C1
~C6
鹵代烷基磺醯基;氨基;單(C1
~C6
烷基)氨基;或是二(C1
~C6
烷基)氨基]。
(2)如(1)所述之化合物或是其鹽,其中,A7
係表示氮原子,
A8
及A9
係分別表示以R8
及R9
取代的碳原子。
(3)如(1)所述之化合物或是其鹽,其中,A7
係表示氮原子,
且A3
, A4
, A5
, A6
, A8
及A9
係分別表示以R3
, R4
, R5
, R6
, R8
及R9
取代的碳原子。
(4)如(3)所述之化合物或是其鹽,其中,R3
, R4
, R5
, R6
, R8
及R9
係分別獨立且表示氫原子、鹵素原子、C1
~C6
鹵代烷基、C1
~C6
鹵代烷氧基、或未取代或以R11
任意取代的雜環基。
(5)如(1)~(4)中任一項所述之化合物或是其鹽,其中,R2
係表示C1
~C6
烷基。
(6)如(1)~(5)中任一項所述之化合物或是其鹽,其中,R1 0
係表示C1
~C12
鹵代烷基。
(7)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(A)
(式中,n, R4
, R8
, R9
及R1 0
係與在(1)中具相同意義)
所表示的化合物。
(8)如(7)所述之化合物或是其鹽,其中,n為2,R4
為C1
~C6
鹵代烷基、C1
~C6
鹵代烷氧基、或是未取代或以R11
任意取代的雜環基,R8
及R9
係分別獨立為氫原子或鹵素原子,R1 0
為C1
~C6
鹵代烷基。
(9)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(B)
(式中,n, R3
, R5
, R6
, R8
, R9
及R1 0
係與(1)中具相同意義)
所表示的化合物。
(10)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(C)
(式中,n, R3
, R4
, R5
, R6
, R8
, R9
及R1 0
係與(1)中具相同意義)
所表示的化合物。
(11)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(D)
(式中,R3
, R4
, R5
, R6
, R8
及R9
係與請求項1中具相同意義)
所表示的化合物。
(12)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(E)
(式中,m, n, R1
, R2
, R4
, R5
, R8
, R9
及R1 0
係與(1)中具相同意義)
所表示的化合物。
(13)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(F)
(式中,n, R2
, R4
, R5
, R8
, R9
及R1 0
係與(1)中具相同意義)
所表示的化合物。
(14)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(G)
(G
)
(式中,n, R2
, R4
, R8
, R9
及R1 0
係與(1)中具相同意義)
所表示的化合物。
(15)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(H)
(式中,n, R2
, R5
, R6
, R8
, R9
及R1 0
係與(1)中具相同意義)
所表示的化合物。
(16)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(I)
(式中,n, R2
, R4
, R5
, R8
, R9
及R1 0
係與請求項1中具相同意義)
所表示的化合物。
(17)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(J)
(式中,n, A3
, A4
, A5
, A6
, R2
, R8
, R9
及R1 0
係與(1)中具相同意義)
所表示的化合物。
(18)如(1)所述之化合物或是其鹽,其中,以通式[I]所表示的化合物係為以通式(K)
(式中,n, A6
, A7
, A8
, A9
, R2
, R4
及R1 0
係與(1)中具相同意義)
所表示的化合物。
(19)一種農藥組合物,其中含有如(1)~(18)所述之化合物或是其農業上可允許的鹽以作為有效成分。
(20)如請求項19所述之農藥組合物,其中,農藥組合物還含有表面活性劑。
(21)一種有害生物防治劑,其中含有如(1)~(18)所述之化合物或是其鹽,以作為活性成分。
(22)如(21)所述之有害生物防治劑,其中,有害生物防治劑係為殺蟲劑、殺線蟲劑及殺蟎劑。
(23)如(22)所述之有害生物防治劑,其對於用於栽培農園藝用植物的稻田、田地、草皮、果園、非農耕地、溫室、育苗設施、植物工廠中的有害生物具有防治效力。
(24)如(23)所述之有害生物防治劑,其中,所述農園藝用植物係為透過育種方法或基因重組技術而被賦予抗性的植物。
(25)一種有害生物的防治方法,其係使用如(1)~(18)所述之化合物或是其鹽的有效成分量。
(26)一種有害生物的防治方法,其係使含有如(1)~(18)所述之化合物或是其鹽為有效成分的農藥組合物,同時地或是分開地,對於使農園藝用作物;或是欲使生長或已生長著農園藝用作物的場所,產生作用。
(27)如(25)或(26)所述之有害生物的防治方法,其中,施用有害生物防治劑的場所係為稻田、田地、草皮、果園、非農耕地、溫室、育苗設施、植物工廠。
(28)如(25)~(27)中任一項所述之有害生物的防治方法,其中,使用如(1)~(18)所述之化合物或是其鹽,以作為殺蟲劑、殺線蟲劑及殺蟎劑使用。
(29)一種有害生物防治劑的使用方法,其係將如(21)~(24)中任一項所述之有害生物防治劑,使用於防治農園藝用作物的有害生物。
(30)一種化合物或是其鹽,其中,於所述通式[I]當中,R1 0
為氫原子的化合物或是其鹽。
(31)一種化合物的製造方法,其特徵在於,所述化合物係為如(1)所述之通式[I]所表示的化合物,且係以如(30)所述之化合物或是其鹽為原料。
[發明功效]
本發明的以通式[I]所表示的化合物係具有優異的有害生物防治作用,於例如龜甲蟲目害蟲、蝶目害蟲、甲蟲目害蟲、蠅目害蟲、蜂目害蟲、蝙蝠目害蟲、薊馬目害蟲、蜘蛛目害蟲、植物寄生線蟲等廣範圍的有害生物具有優異的防治功效。此外,也可防治已具抗藥性的有害生物。
尤其是,含有本發明化合物之有害生物防治劑係對於以下有害生物具有卓越的功效:蜘蛛蟎類,其係以例如娜美蜘蛛蟎、金澤蜘蛛蟎、柑橘葉蟎等作為代表;龜甲目害蟲類,其係以例如褐飛蝨、偽黑尾葉蟬、綿蚜為代表;甲蟲目害蟲類,其係以例如稻水象蟲、稻負泥蟲、金龜子為代表;線蟲類,例如紅薯線蟲等;以及蝶目害蟲,其係以例如小菜蛾、二化螟、番茄夜蛾作為代表。此外,由於其具有優異的滲透傳遞性,因此可進行基於土壤處理所作的安全且省力的施用方法。
針對本說明中所記載之元件符號及用語進行說明。
於本發明當中,「有害生物防治劑」係意指用於農業園藝領域、家畜寵物等動物、家用或防疫用的:殺蟲劑、殺蟎劑,殺線蟲劑等。
於本發明當中,「鹵素原子」係指氟原子、氯原子、溴原子、碘原子。
於本發明當中,關於「C1
~C6
」等描述,接在元素符號後的數字係表示碳原子數,例如,於此情況下碳原子數可為1~6範圍內中的任一者。
在本發明中,除非另有限定,否則「C1
~C6
烷基」係指具有1~6個碳原子的直鏈或支鏈的烷基,可列舉例如:甲基、乙基、正丙基、異丙基、正丁基、仲丁基、異丁基、叔丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、新戊基、正己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1-乙基丁基、2-乙基丁基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基,3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、或1-乙基-2-甲基丙基等基團。
於本發明中,除非另有限定,「C1
~C12
烷基」係表示具有1~12個碳原子的直鏈狀或支鏈狀的烷基,例如:甲基、乙基、丙基、異丙基、丁基、仲丁基、異丁基、叔丁基、戊基、1-甲基丁基、2-甲基丁基、異戊基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、新戊基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、異己基、1-乙基丁基、2-乙基丁基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、庚基、1-甲基己基、2-甲基己基、3-甲基己基、4-甲基己基、異庚基、1,1-二甲基戊基、2,2-二甲基戊基、4,4-二甲基戊基、1-乙基戊基、2-乙基戊基、1,1,3-三甲基丁基、1,2,2-三甲基丁基、1,3,3-三甲基丁基、2,2,3-三甲基丁基、2,3,3-三甲基丁基、1-丙基丁基、1,1,2,2-四甲基丙基、辛基、1-甲基庚基、3-甲基庚基、異辛基、2-乙基己基、5,5-二甲基己基、2,4,4-三甲基戊基、1-乙基-1-甲基戊基、1-丙基戊基、壬基、1-甲基辛基、2-甲基辛基、3-甲基辛基、異壬基、1-乙基庚基、1,1-二甲基庚基、6,6-二甲基庚基、癸基、1-甲基壬基、2-甲基壬基、6-甲基壬基、異癸基、1-乙基辛基、1-丙基庚基、十一烷基、1-甲基癸基、異十六烷基、十二烷基、1-甲基十一烷基、異十二烷基等。
於本發明中,除非另有限定,「C1
~C6
鹵代烷基」係表示由具有相同或相異1~13個鹵素原子所取代,且碳原子數量為1~6的直鏈狀或支鏈狀的鹵代烷基,例如:氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、碘甲基、氯二氟甲基、二氯氟甲基、1-氟乙基、2-氟乙基、 1,1-二氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、1,1,2,2-四氟乙基、五氟乙基、1-氯乙基、2-氯乙基、1,1-二氯乙基、2,2-二氯乙基、2,2,2-三氯乙基、1,1,2,2-四氯乙基、五氯乙基、1-溴乙基、2-溴乙基、2,2,2-三溴乙基、1-碘乙基、2-碘乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2-三氯乙基、1-氟丙基、2-氟丙基、3-氟丙基、1,1-二氟丙基、2,2-二氟丙基、3,3-二氟丙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-氟丙烷-2-基、2-氟丙烷-2-基、1,1-二氟丙烷-2-基、1,2-二氟丙烷-2-基、1,3-二氟丙烷-2-基、1,2,3-三氟丙烷-2-基、1,1,3,3-四氟丙烷-2-基、1,1,1,3,3,3-六氟丙烷-2-基、七氟丙烷-2-基、1-氯丙基、2-氯丙基、3-氯丙基、1,1-二氯丙基、2,2-二氯丙基、3,3-二氯丙基、3,3,3-三氯丙基、2,2,3,3,3-五氯丙基、七氯丙基、1-氯丙烷-2-基、2-氯丙烷-2-基、1,1-二氯丙烷-2-基、1,2-二氯丙烷-2-基、1,3-二氯丙烷-2-基、1,2,3-三氯丙烷-2-基、1,1,3,3-四氯丙烷-2-基、1,1,1,3,3,3-六氯丙烷-2-基、七氯丙烷-2-基、1-溴丙基、2-溴丙基、3-溴丙基、1-溴丙烷-2-基、2-溴丙烷-2-基、1-碘丙基、2-碘丙基、3-碘丙基、1-碘丙烷-2-基、2-碘丙烷-2-基、1-氟丁基、2-氟丁基、3-氟丁基、4-氟丁基、4,4-二氟丁基、4,4,4-三氟丁基、3,3,4,4,4-五氟丁基、2,2,3,3,4,4,4-七氟丁基、九氟丁基、1,1,1-三氟丁烷-2-基、4,4,4-三氟丁烷-2-基、3,3,4,4,4-五氟丁烷-2-基、九氟丁烷-2-基、1,1,1,3,3,3-六氟-2-(三氟甲基)丙烷-2-基、1-氯丁基、2-氯丁基、3-氯丁基、4-氯丁基、4,4-二氯丁基、4,4,4-三氯丁基、九氯丁基、1,1,1-三氯丁烷-2-基、4,4,4-三氯丁烷-2-基、九氯丁烷-2-基、1-溴丁基、2-溴丁基、3-溴丁基、4-溴丁基、1-碘丁基、2-碘丁基、3-碘丁基、4-碘丁基、4-氯-1,1,2,2,3,3,4,4-八氟丁基、4-溴-1,1,2,2,3,3,4,4-八氟丁基、1-氟戊基、2-氟戊基、3-氟戊基、4-氟戊基、5-氟戊基、5,5,5-三氟戊基、4,4,5,5,5-五氟戊基、3,3,4,5,5,5-七氟戊基、2,2,3,3,4,4,5,5,5-壬氟戊基、十一氟戊基、1-氯戊基、2-氯戊基、3-氯戊基、4-氯戊基、5-氯戊基、5,5,5-三氯戊基、4,4,5,5,5-五氯戊基、3,3,4,4,5,5,5-七氯戊基、2,2,3,3,4,4,5,5,5-九氯戊基、十一氯戊基、1-溴戊基、2-溴戊基、3-溴戊基、4-溴戊基、5-溴戊基、5-碘戊基、1-氟己基、2-氟己基、3-氟己基、4-氟己基、5-氟己基、6-氟己基、6,6,6-三氟己基、5,5,6,6,6-五氟己基、4,4,5,5,6,6,6-七氟己基、3,3,4,4,5,5,6,6,6-九氟己基、2,2,3,3,4,4,5,5,6,6,6-十一碳氟己基、十三氟己基、1-氯己基、2-氯己基、3-氯己基、4-氯己基、5-氯己基、6-氯己基、5-溴己基、6-溴己基、5-碘己基,或是6-碘己基等之基團。
於本發明中,除非另有限定,「C1
~C12
鹵代烷基」係表示由具有相同或相異的1~25個鹵素原子所取代且碳原子數量為1~12的直鏈狀或支鏈狀的烷基,例如:前述「C1
~C6
鹵代烷基」中的示例、2,2,3,4,4,6,6,6-八氟-3,5,5-三(三氟甲基)己基、1H,1H-全氟庚基、1H,1H,2H,2H-全氟庚基、1H,1H,2H,2H,3H,3H-全氟庚基、1H,1H,7H-全氟庚基、全氟庚基、2-(全氟-3-甲基丁基)乙基、1H,1H-全氟辛基、1H,1H,2H,2H-全氟辛基、1H,1H,2H,2H,3H,3H-全氟辛基、6-(全氟己基)乙基、1H,1H,8H-全氟辛基、全氟辛基、1H,1H-全氟壬基、1H,1H,2H,2H-全氟壬基、1H,1H,2H,2H,3H,3H-全氟壬基、6-(全氟-1-甲基乙基)己基、1H,1H,9H-全氟壬基、全氟壬基、1H,1H-全氟癸基、1H,1H,2H,2H-全氟癸基、1H,1H,2H,2H,3H,3H-全氟癸基、6-(全氟丁基)己基、1H,1H,9H-全氟癸基、全氟癸基等。
於本發明中,除非另有限定,「C3
~C6
環烷基」係表示碳原子數量為3~6的環烷基,可列舉例如環丙基、環丁基、環戊基、環己基等。
於本發明中,除非另有限定,「C3
~C6
鹵代環烷基」係表示由相同或不同的1~11個鹵素原子所取代,且碳原子數量為3~6的環烷基,例如:
1-氟環丙基、2-氟環丙基、2,2-二氟環丙基、2,2,3,3-四氟環丙基、1-氯環丙基、2-氯環丙基、2,2-二氯環丙基、2,2,3,3-四氯環丙基、2,2-二溴環丙基、2,2-二碘環丙基、1-氟環丁基、2-氟環丁基、3-氟環丁基、3,3-二氟環丁基、七氟環丁基、2-氯環丁基、3-氯環丁基、3,3-二氯環丁基、3,3-二溴環丁基、3,3-二碘環丁基、1-氟環戊基、2-氟環戊基、3-氟環戊基、2,2-二氟環戊基、3,3-二氟環戊基、九氟環戊基、2,2-二氯環戊基、3,3-二氯環戊基、2,2-二溴環戊基、3,3-二溴環戊基、2,2-二碘環戊基、3,3-二碘環戊基、1-氟環己基、2-氟環己基、3-氟環己基、4-氟環己基、2,2-二氟環己基、3,3-二氟環己基、4,4-二氟環己基、1-氯環己基、2-氯環己基、3-氯環己基、4-氯環己基、2,2-二氯環己基、3,3-二氯環己基、4,4-二氯環己基、3,3-二溴環己基、4,4-二溴環己基、3,3-二碘環己基、或是4,4-二碘環己基等基團。
於本發明中,除非另有限定,「C2
~C6
烯基」係表示碳原子數量為2~6的直鏈狀或支鏈狀的烯基,例如:乙烯基、1-丙烯基、異丙烯基、2-丙烯基、1-丁烯基、1-甲基-1-丙烯基、2-丁烯基、1-甲基-2-丙烯基、3-丁烯基、2-甲基-1-丙烯基、 2-甲基-2-丙烯基、1,3-丁二烯基、1-戊烯基、1-乙基-2-丙烯基、2-戊烯基、1-甲基-1-丁烯基、3-戊烯基、1-甲基-2-丁烯基、4-戊烯基、1-甲基-3-丁烯基、3-甲基-1-丁烯基、1,2-二甲基-2-丙烯基、1,1-二甲基-2-丙烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1,2-二甲基-1-丙烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,3-戊二烯基、1-乙烯基-2-丙烯基、1-己烯基、1-丙基-2-丙烯基、2-己烯基、1-甲基-1-戊烯基、1-乙基-2-丁烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-4-戊烯基、1-乙基-3-丁烯基、1-(異丁基)乙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-2-丙烯基、1-(異丙基)-2-丙烯基、2-甲基-2-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1,3-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1,5-己二烯基、1-乙烯基-3-丁烯基或是2,4-己二烯基等之基團。
於本發明中,除非另有限定,「C2
~C6
鹵代烯基」係表示由相同或不同的1~11個鹵素原子所取代,且碳原子數量為2~6的直鏈狀或支鏈狀的烯基,例如:1-氟乙烯基、2-氟乙烯基、1,2-二氟乙烯基、2,2-二氟乙烯基、三氟乙烯基、1-氯乙烯基、2-氯乙烯基、1,2-二氯乙烯基、2,2-二氯乙烯基、三氯乙烯基、1,2-二溴乙烯基、2,2-二溴乙烯基、三溴乙烯基、1,2-二碘乙烯基、2,2-二碘乙烯基、三碘乙烯基、1-氟-2-丙烯基、2-氟-2-丙烯、3-氟-2-丙烯基、2,3-二氟-2-丙烯基、3,3-二氟-2-丙烯基、3,3-二氟-1-丙烯基、2,3,3-三氟-2-丙烯基、3,3,3-三氟-1-丙烯基、2-氯-3,3,3-三氟-1-丙烯基、1,2,3,3,3-五氟-1-丙烯基、1-氯-2-丙烯基、2-氯-2-丙烯基、3-氯-2-丙烯基、2,3-二氯-2-丙烯基、3,3-二氯-2-丙烯基、3,3-二氯-1-丙烯基、2,3,3-三氯-2-丙烯基、3,3,3-三氯-1-丙烯基、3-溴-2-丙烯基、3,3-二溴-2-基丙烯基、3,3-二碘-2-丙烯基、2,2-二氟-1-丙烯-2-基、3,3,3-三氟-1-丙烯-2-基、3,3,3-三氯-1-丙烯-2-基、4-氟-3-丁烯基、4,4-二氟-3-丁烯基、4,4-二氟-3-丁烯-2-基、4,4,4-三氟-2-丁烯基、3,4,4-三氟-3-丁烯基、2-三氟甲基-2-丙烯基、2-三氟甲基-3,3-二氟-2-丙烯基、4,4,4-三氟-3-氯-2-丁烯基、4,4-二氯-3-丁烯基、4,4,4-三氯-2-丁烯基、2-三氯甲基-2-丙烯基、5,5-二氟-4-戊烯基、4,5,5-三氟-4-戊烯基、5,5,5-三氟-3-戊烯基、4,4,4-三氟-3-甲基-2-丁烯基、4,4,4-三氟-3-三氟甲基-2-丁烯基、5,5-二氯-4-戊烯基、4,4,4-三氯-3-甲基-2-丁烯基、6,6-二氟-5-己烯基、5,6,6-三氟-5-戊烯基、6,6,6-三氟-4-戊烯基、5,5,5-三氟-4-甲基-3-戊烯基、5,5,5-三氟-4-三氟甲基-3-戊烯基、6,6-二氯-5-己烯基、或是5,5,5-三氯-4-甲基-3-戊烯基等之基團。
於本發明中,除非另有限定,「C2
~C6
炔基」係表示碳原子數量為2~6的直鏈狀或支鏈狀的炔基,例如:乙炔基、1-丙炔基、2-丙炔基、1-丁基、1-甲基-2-丙炔基、2-丁炔基、3-丁炔基、1-戊炔基、1-乙基-2-丙炔基、2-戊炔基、3-戊炔基、1-甲基-2-丁炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-己炔基、1-(正丙基)-2-丙炔基、2-己炔基、1-乙基-2-丁炔基、3-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、4-甲基-1-戊炔基、3-甲基-1-戊炔基、5-己炔基、1-乙基-3-丁炔基、1-乙基-1-甲基-2-丙炔基、1-(異丙基)-2-丙炔基、1,1-二甲基-2-丁炔基、或是2,2-二甲基-3-丁炔基等之基團。
於本發明中,除非另有限定,「C2
~C6
鹵代炔基」係表示由相同或是不同的1~9個鹵素原子所取代,且碳原子數量為2~6的直鏈狀或支鏈狀的炔基,例如:氟乙炔基、氯乙炔基、溴乙炔基、碘乙炔基、3-氟-2-丙炔基、3-氯-2-丙炔基、3-溴-2-丙炔基、3-碘-2-丙炔基、4-氟-3-丁炔基、4-氯-3-丁炔基、4-溴-3-丁炔基、4-碘-3-丁炔基、4,4-二氟-2-丁炔基、4,4-二氯-2-丁炔基、4,4,4-三氟-2-丁炔基、4,4,4-三氯-2-丁炔基、3-氟-1-甲基-2-丙炔基、3-氯-1-甲基-2-丙炔基、5-氟-4-戊炔基、5-氯-4-戊炔基、5,5,5-三氟-3-戊炔基、5,5,5-三氯-3-戊炔基、4-氟-2-甲基-3-丁炔基、4-氯-2-甲基-3-丁炔基、6-氟-5-己炔基、6-氯-5-己炔基、6,6,6-三氟-4-己炔基、6,6,6-三氯-4-己基、5-氟-3-甲基-4-戊炔基、或是5-氯-3-甲基-4-戊炔基等之基團。
於本發明中,除非另有限定,「C3
~C6
環烷基C2
~C6
炔基」係表示環烷基部分及炔基部分為上述意義的(C3
~C6
環烷基)-(C2
~C6
炔基)之基團,可列舉例如上述「C3
~C6
環烷基」及「C2
~C6
炔基」中示例內容的任意組合。
於本發明當中,除非另有限定,「C1
~C6
烷氧基」係表示烷基部分為上述意義的(C1
~C6
烷基)-O-基,例如:甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、仲丁氧基、叔丁氧基、正戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、1-乙基丙氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、或是正己氧基等之基團。
於本發明中,除非另有限定,「C1
~C6
鹵代烷氧基」係表示鹵代烷基部分係為上述意義的(C1
~C6
鹵代烷基)-O-基,例如:二氟甲氧基、二氯甲氧基、三氟甲氧基、三氯甲氧基、三溴甲氧基、氯二氟甲氧基、溴二氟甲氧基、2-氟乙氧基、1-氯乙氧基、2-氯乙氧基、1-溴乙氧基、2-溴乙氧基、2,2-二氟乙氧基、1,2-二氯乙氧基、2,2-二氯乙氧基、2,2,2-三氟乙氧基、2,2,2-三氯乙氧基、1,1,2,2-四氟乙氧基、五氟乙氧基、2-溴-2-氯乙氧基、2-氯-1,1,2,2-四氟乙氧基、1-氯-1,2,2,2-四氟乙氧基、1-氯丙氧基、2-氯丙氧基、3-氯丙氧基、2-溴丙氧基、3-溴丙氧基、2-溴-1-甲基乙氧基、3-碘丙氧基、2,3-二氯丙氧基、2,3-二溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氟-2-丙氧基、3,3,3-三氯丙氧基、3-溴-3,3-二氟丙氧基、 2,2-二氟丙氧基、3,3-二氯-3-氟丙氧基、2,2,3,3-四氟丙氧基、1-溴-3,3,3-三氟丙氧基、2,2,3,3,3-五氟丙氧基、2,2,2-三氟-1-三氟甲基乙氧基、七氟丙氧基、七氟-2-丙氧基、1,2,2,2-四氟-1-三氟甲基乙氧基、1,1,2,3,3,3-六氟丙氧基、2-氯丁氧基、3-氯丁氧基、4-氯丁氧基、2-氯-1,1-二甲基乙氧基、4-溴丁氧基、3-溴-2-甲基丙氧基、2-溴-1,1-二甲基乙氧基、2,2-二氯-1,1-二甲基乙氧基、2-氯-1-氯甲基-2-甲基乙氧基、4,4,4-三氟丁氧基、3,3,3-三氟-1-甲基丙氧基、3,3,3-三氟-2-甲基丙氧基、2,3,4-三氯丁氧基、2,2,2-三氯-1,1-二甲基乙氧基、4-氯-4,4-二氟丁氧基、4,4-二氯-4-氟丁氧基、4-溴- 4,4-二氟丁氧基、2,4-二溴-4,4-二氟丁氧基、3,4-二氯-3,4,4-三氟丁氧基、3,3-二氯-4,4,4-三氟丁氧基、4-溴-3,3,4,4-四氟丁氧基、4-溴-3-氯-3,4,4-三氟丁氧基、2,2,3,3,4,4-六氟丁氧基、2,2,3,4,4,4-六氟丁氧基、2,2,2-三氟-1-甲基-1-三氟甲基乙氧基、3,3,3-三氟-2-三氟甲基丙氧基、2,2,3,3,4,4,4-七氟丁氧基、3,3,4,4,4-五氟-2-丁氧基、2,3,3,3-四氟-2-三氟甲基丙氧基、1,1,2,2,3,3,4,4-八氟丁氧基、九氟丁氧基、全氟叔丁氧基、4-氯-1,1,2,2,3,3,4,4-八氟丁氧基、5,5,5-三氟戊氧基、4,4,5,5,5-五氟戊氧基、3,3,4,4,5,5,5-七氟戊氧基、3,3,4,4,5,5,5-七氟-2-戊氧基、2,2,3,3,4,4,5,5,5-九氟戊氧基、2,2,3,3,4,4,5,5-八氟戊氧基、全氟戊氧基、4,4,5,5,5-五氟-2-丁氧基、2,2-雙(三氟甲基)丙氧基、2,2,3,3,4,4,5,5,6,6,6-十一碳氟己氧基、3,3,4,4,5,5,6,6,6-正氟己氧基、4,4,5,5,6,6,6-七氟己氧基、2,2,3,3,4,4,5,5,6,6-十氟己氧基、4,4,4-三氟-3,3-雙(三氟甲基)丁氧基、全氟己氧基等基團。
於本發明中,除非另有限定,「C1
~C6
烷氧基C1
~C6
烷基」係表示烷氧基部分及烷基部分為上述意義的(C1
~C6
烷氧基)-(C1
~C6
烷基)之基團,可列舉例如:甲氧基甲基、乙氧基甲基、正丙氧基甲基、異丙氧基甲基、叔丁氧基甲基、1-甲氧基乙基、1-甲氧基-1-甲基乙基、2-甲氧基乙基、1-乙氧基乙基、2-乙氧基乙基、 2-異丙氧基乙基、3-甲氧基丙基、2-甲氧基丙基、3-乙氧基丙基、4-甲氧基丁基、或是4-乙氧基丁基等之基團。
於本發明中,除非另有限定,「C1
~C6
烷氧基C1
~C6
鹵代烷基」係表示烷氧基部分及鹵代烷基部分為上述意義的(C1
~C6
烷氧基)-(C1
~C6
鹵代烷基)之基團,可列舉例如上述「C1
~C6
烷氧基」及「C1
~C6
鹵代烷基」中示例內容的任意組合。
於本發明中,除非另有限定,「C1
~C6
鹵代烷氧基C1
~C6
烷基」係表示鹵代烷氧基部分及烷基部分為上述意義的(C1
~C6
鹵代烷氧基)-(C1
~C6
烷基)之基團,可列舉例如上述「C1
~C6
鹵代烷氧基」及「C1
~C6
烷基」中所示例內容的任意組合。
於本發明中,除非另有限定,「C1
~C6
鹵代烷氧基C1
~C6
鹵代烷基」係表示鹵代烷氧基部分及鹵代烷基部分為上述意義的(C1
~C6
鹵代烷氧基)-(C1
~C6
鹵代烷基)之基團,可列舉例如於上述「C1
~C6
鹵代烷氧基」及「C1
~C6
鹵代烷基」中所示例內容的任意組合。
於本發明中,除非另有限定,「C3
~C6
環烷基C1
~C6
烷基」係表示環烷基部分及烷基部分為上述意義的(C3
~C6
環烷基)-(C1
~C6
烷基)之基團,例如於「C3
~C6
環烷基」及「C1
~C6
烷基」中所示例內容的任意組合。
於本發明中,除非另有限定,「C3
~C6
鹵代環烷基C1
~C6
烷基」係表示鹵代環烷基部分及烷基部分為上述意義的(C3
~C6
鹵代環烷基)-(C1
~C6
烷基)之基團,可列舉例如於上述「C3
~C6
鹵代環烷基」及「C1
~C6
烷基」中所示例內容的任意組合。
於本發明中,除非另有限定,「C1
~C6
鹵代烷氧基C1
~C6
烷氧基」係表示鹵代烷氧基部分及烷氧基部分為上述意義的(C1
~C6
鹵代烷氧基)-(C1
~C6
烷氧基)之基團,可列舉例如於上述「C1
~C6
鹵代烷基」及「C1
~C6
烷基」中所示例內容的任意組合。
於本發明中,除非另有限定,「C1
~C6
烷氧基C1
~C6
鹵代烷基」係表示烷氧基部分及鹵代烷氧基部分為上述意義的(C1
~C6
烷氧基)-(C1
~C6
鹵代烷氧基) 之基團,可列舉例如於上述「C1
~C6
烷氧基」及「C1
~C6
鹵代烷基」中所示例內容的任意組合。
於本發明中,除非另有限定,「C1
~C6
鹵代烷氧基C1
~C6
鹵代烷氧基」係表示鹵代烷氧基部分及鹵代烷氧基部分為上述意義的(C1
~C6
鹵代烷氧基)-(C1
~C6
鹵代烷氧基)之基團,可列舉例如於上述「C1
~C6
鹵代烷氧基」及「C1
~C6
鹵代烷氧基」中所示例內容的任意組合。
於本發明中,除非另有限定,「C3
~C6
環烷基氧基」係指環烷基部分為上述意義的(C3
~C6
環烷基)-O-基,可列舉例如:環丙氧基、環丁氧基、環戊氧基、環己氧基等之基團。
於本發明中,除非另有限定,「C3
~C6
鹵代環烷基氧基」係表示鹵代環烷基部分為上述意義的(C3
~C6
鹵代環烷基)-O-基,可列舉例如:2,2-二氟環丙氧基、2,2-二氯環丙氧基、3,3-二氟環丁氧基、3,3-二氯環丁氧基、3-氟環戊氧基、3,3-二氟環戊氧基、九氟環戊氧基、3,3-二氯環戊氧基、4,4-二氟環己氧基、或是4,4-二氯環己氧基等之基團。
於本發明中,除非另有限定,「C3
~C6
環烷基C1
~C6
烷氧基」係表示環烷基部分及烷氧基部分為上述意義的(C3
~C6
環烷基)-(C1
~C6
烷氧基)之基團,可列舉例如:環丙基甲氧基、環丁基甲氧基、環戊基甲氧基、或是環己基甲氧基等之基團。
於本發明中,除非另有限定,「C3
~C6
鹵代環烷基C1
~C6
烷氧基」係表示鹵代環烷基部分及烷氧基部分為上述意義的(C3
~C6
鹵代環烷基)-(C1
~C6
烷氧基)之基團,可列舉例如:1-氟環丙基甲氧基、1-氯環丙基甲氧基、1-溴環丙基甲氧基、1-氟環丁基甲氧基、1-氯環丁基甲氧基、1-溴環丁基甲氧基、2,2-二氟環丙基甲氧基、2,2-二氯環丙基甲氧基、3,3-二氟環丁基甲氧基等之基團。
於本發明中,除非另有限定,「C6
~C12
芳基」係表示具有6~12個碳原子的芳基,可列舉例如苯基、1-萘基、2-萘基等之基團。1-萘基也可稱為萘-1-基。2-萘基也可稱為萘-2-基。
於本發明中,除非另有限定,「C6
~C12
芳氧基」係表示(C6
~C12
芳基)-O-基,可列舉例如苯氧基、萘-1-基氧基、萘-2-基氧基等之基團。
於本發明中,除非另有限定,「C6
~C12
芳基羰基」表示(C6
~C12
芳基)-C(=O)-基,例如苯甲醯基、1-萘甲醯基、或2-萘甲醯基等之基團。
於本發明中,除非另有限定,「C7
~C1 4
芳烷基」係表示具有7~14個碳原子,且由芳基所取代的烷基。可列舉例如:C6
~C1 0
芳基C1
~C4
烷基、C6
~C1 0
芳基C1
~C2
烷基、苯基C1
~C2
烷基等之基團。C7
~C1 4
芳烷基的具體示例可列舉芐基、1-苯乙基、2-苯乙基、3-苯丙基、4-苯丙基、萘-1-基甲基和萘-2-基甲基等之基團。此外,芳烷基(Aralkyl)也稱為芳基烷基(Arylalkyl)。
於本發明中,除非另有限定,「C6
~C12
雜芳烷基」係表示具有6~12個碳原子,且由雜芳基取代為C5
~C1 0
雜芳基C1
~C2
烷基的烷基,可列舉例如啶基甲基(pyridylmethyl),吲哚基甲基(indolylmethyl),呋喃基甲基(furylmethyl),噻吩基甲基(thienylmethyl)和吡咯基甲基(prrolylmethyl)等之基團。
於本發明中,除非另有限定,「C7
~C1 4
芳烷氧基」係表示芳烷基部分為上述意義的(C7
~C1 4
芳烷基)-O-基,可列舉例如芐氧基、1-苯乙氧基、2-苯乙氧基、3-苯丙氧基、4-苯丙氧基、萘-1-基甲氧基、萘-2-基甲氧基等之基團。
於本發明中,除非另有限定,「C6
~C12
雜芳烷基氧基」係表示雜芳烷基部分為上述意義的(C6
~C12
雜芳烷基)-O-基,可列舉例如吡啶基甲氧基、吲哚基甲氧基、呋喃基甲氧基、噻吩基甲氧基、吡咯基甲基等之基團。
於本發明中,「C5
~C12
雜芳基」係意指具有由O、S及N當中所選1個以上的雜原子作為環原子,且環結構係為包含5~12個環原子的單環式或縮合雙環式結構。藉由包含雜原子來使得與6元環相同的5元環中的芳香性為可行。作為典型的雜原子系,可列舉例如使單環式5~6元環的芳族基及苯環;或是雜芳族單環式之基團中的其中之一,縮合為C8
~C1 0
雙環式之基團所形成的縮合雙環式部分,例如:吲哚、苯並咪唑基、吲唑基、苯並三唑基、異喹啉基、喹啉基、苯並噻唑基、苯並呋喃基、苯並噻吩基、苯並異噁唑基、吡唑並吡啶基、喹唑啉基、喹喔啉基、肉桂酸酯及其他類似物。所述單環式5~6元環的芳族基可為例如吡啶基、嘧啶基、吡嗪基、吡啶基、三嗪基、噻吩基、呋喃基、吡咯基、吡唑基、噻唑基、異噻唑基、噁唑基、異噁唑基、咪唑基、三唑基、噻二唑基、惡二唑基、及四唑基環,以及此等單環式之基團的其中之一。
於本發明中,「C5
~C12
雜芳基氧基」係意指(C5
~C12
雜芳基)-O-基(於此,C5
~C12
雜芳基具有與上述定義相同的意思)。
於本發明中,除非另有限定,「C1
~C6
烷硫基」,係表示烷基部分為上述意義的(C1
~C6
烷基)-S-基,可列舉例如甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、仲丁硫基或叔丁硫基、戊硫基、己硫基等之基團。
於本發明中,除非另有限定,「C1
~C6
烷基亞磺醯基」係表示烷基部分為上述意義的(C1
~C6
烷基)-S(=O)-基,可列舉例如:甲基亞磺醯基、乙基亞磺醯基、正丙基亞磺醯基、異丙基亞磺醯基、正丁基亞磺醯基、異丁基亞磺醯基、仲丁基亞磺醯基、叔丁基亞磺醯基、戊基亞磺醯基、己基亞磺醯基。
於本發明中,除非另有限定,「C1
~C6
烷基磺醯基」係表示烷基部分為上述意義的(C1
~C6
烷基)-S(=O)2
-基,可列舉例如:甲基磺醯基、乙基磺醯基、正丙基磺醯基、異丙基磺醯基、正丁基磺醯基、異丁基磺醯基、仲丁基磺醯基、叔丁基磺醯基、戊磺醯基、或是己磺醯基等之基團。
於本發明中,除非另有說明,「C1
~C6
鹵代烷硫基」係表示鹵代烷基部分為上述意義的(C1
~C6
鹵代烷基)-S-基,可列舉例如:氟甲硫基、二氟甲硫基、三氟甲硫基、三氯甲硫基、2,2,2-三氟乙硫基、五氟乙硫基、2,2,2-三氯乙硫基、3,3,3-三氟丙硫基、1,1,2,3,3,3-六氟丙硫基、七氟丙硫基、1,1,1,3,3,3-六氟丙烷-2-基硫基、七氟丙烷-2-基硫基、或是4,4,4-三氟丁硫基。
於本發明中,除非另有說明,「C1
~C6
鹵代烷基亞磺醯基」係表示鹵代烷基部分為上述意義的(C1
~C6
鹵代烷基)-S(=O)-基,可列舉例如:二氟甲基亞磺醯基、三氟甲基亞磺醯基、三氯甲基亞磺醯基、2,2,2-三氟乙基亞磺醯基、2,2,2-三氯乙基亞磺醯基、五氟乙基亞磺醯基、3,3,3-三氟丙基亞磺醯基、 七氟丙基亞磺醯基、或是七氟-2-丙基亞磺醯基等之基團。
於本發明中,除非另有說明,「C1
~C6
鹵代烷基磺醯基」係表示鹵代烷基部分為上述意義的(C1
~C6
鹵代烷基)-S(=O)2
-基,可列舉例如:二氟甲基磺醯基、三氟甲基磺醯基、三氯甲基磺醯基、2,2,2-三氟乙基磺醯基、五氟乙基磺醯基、3,3,3-三氟丙基磺醯基、七氟丙基磺醯基、或是七氟-2-丙基磺醯基等之基團。
於本發明中,除非另有說明,「C3
~C6
環烷基硫基」係表示環烷基部分為上述意義的(C3
~C6
環烷基)-S-基,例如環丙硫基、環丁硫基、環戊硫基、或是環己硫基等之基團。
於本發明中,除非有特別限定,「C3
~C6
環烷基亞磺醯基」係表示環烷基部分為上述意義的(C3
~C6
環烷基)-S(=O)-基,可列舉例如:環丙基亞磺醯基、環丁基亞磺醯基、環戊基亞磺醯基、或是環己基亞磺醯基等之基團。
於本發明中,除非另有限定,「C3
~C6
環烷基磺醯基」係表示環烷基部分為上述意義的(C3
~C6
環烷基)-S(=O)2
-基,可列舉例如:環丙基磺醯基、環丁基磺醯基、環戊基磺醯基、或是環己基磺醯基等之基團。
於本發明中,除非另有限定,「C3
~C6
鹵代環烷基硫基」係表示環烷基部分為上述意義的(C3
~C6
鹵代環烷基)-S-基,可列舉例如:2,2-二氟環丙硫基、2,2-二氯環丙硫基、3,3-二氟環丁硫基、3,3-二氯環丁硫基、3-氟環戊硫基、3,3-二氟環戊硫基、九氟環戊硫基、3,3-二氯環戊硫基、4,4-二氟環己硫基、或是4,4-二氯環己硫基等之基團。
於本發明中,除非另有限定,「C3
~C6
鹵代環烷基亞磺醯基」係表示鹵代環烷基為上述意義的(C3
~C6
鹵代環烷基)-S-基,可列舉例如:2,2-二氟環丙基亞磺醯基、2,2-二氯環丙基亞磺醯基、3,3-二氟環丁基亞磺醯基、3,3-二氯環丁基亞磺醯基、3-氟環戊基亞磺醯基、3,3-二氟環戊基亞磺醯基、九氟環戊基亞磺醯基、3,3-二氯環戊基亞磺醯基、4,4-二氟環己基亞磺醯基、或是4,4-二氯環己基亞磺醯基等之基團。
於本發明中,除非另有限定,「C3
~C6
鹵代環烷基磺醯基」係表示鹵代環烷基部分為上述意義的(C3
~C6
鹵代環烷基)-S-基,可列舉例如:2,2-二氟環丙基磺醯基、2,2-二氯環丙基磺醯基、3,3-二氟環丁基磺醯基、3,3-二氯環丁基磺醯基、3-氟環戊基磺醯基、3,3-二氟環戊基磺醯基、九氟環戊基磺醯基、3,3-二氯環戊基磺醯基、4,4-二氟環己基磺醯基、或是4,4-二氯環己基磺醯基。
於本發明中,除非另有限定,「C6
~C12
芳基硫基」係代表芳基部分為上述意義的(C6
~C12
芳基)-S-基,可列舉例如:苯硫基、1-萘硫基、以及2-萘硫基等之基團。
於本發明中,除非另有特別限定,「C6
~C12
芳基亞磺醯基」係表示芳基部分為上述意義的(C6
~C12
芳基)-S(=O)-基,可列舉例如:苯基亞磺醯基、1-萘亞磺醯基、以及2-萘亞磺醯基等之基團。
於本發明中,除非另有特別限定,「C6
~C12
芳基磺醯基」係表示芳基部分為上述意義的(C6
~C12
芳基)-S(=O)2
-基,可列舉例如:苯磺醯基、1-萘磺醯基、以及2-萘磺醯基等之基團。
於本發明中,除非另有特別限定,「C5
~C12
雜芳基硫基」係表示芳基部分為上述意義的(C5
~C12
雜芳基)-S-基,可列舉例如:吡啶-2-硫醇基、吡啶-3-硫醇基、吡啶-4-硫醇基、吡嗪-2-硫醇基、噠嗪-3-硫醇基、噠嗪-4-硫醇基、嘧啶-2-硫醇基、嘧啶-4-硫醇基、嘧啶-5-硫醇基、噻唑-2-硫醇基、噻唑-4-硫醇基、或是噻唑-5-硫醇基。
於本發明中,除非另有特別限定,「C5
~C12
雜芳基亞磺醯基」係表示芳基部分為上述意義的(C5
~C12
雜芳基)-S(=O)-基,可列舉例如:吡啶-2-基亞磺醯基、吡啶-3-基亞磺醯基、吡啶-4-基亞磺醯基、吡嗪-2-基亞磺醯基、噠嗪-3-基亞磺醯基、噠嗪-4-基亞磺醯基、嘧啶-2-基亞磺醯基、嘧啶-4-基亞磺醯基、嘧啶-5-基亞磺醯基、噻唑-2-基亞磺醯基、噻唑-4-基亞磺醯基、或噻唑-5-基亞磺醯基等之基團。
於本發明中,除非另有特別限定,「C5
~C12
雜芳基磺醯基」係表示芳基部分為上述意義的(C5
~C12
雜芳基)-S(=O)2
-基,可列舉例如:吡啶-2-基磺醯基、吡啶-3-基磺醯基、吡啶-4-基磺醯基、吡嗪-2-基磺醯基、噠嗪-3-基磺醯基、噠嗪-4-基磺醯基、嘧啶-2-基磺醯基、嘧啶-4-基磺醯基、嘧啶基-5-基磺醯基、噻唑-2-基磺醯基、噻唑-4-基磺醯基、或是噻唑-5-基磺醯基等之基團。
於本發明中,除非另有特別限定,「C1
~C6
烷硫基C1
~C6
烷基」係表示烷硫基部分及烷基部分為上述意義的(C1
~C6
烷硫基)-(C1
~C6
烷基)之基團,可列舉例如:甲硫基甲基、2-(甲硫基)乙基、3-(甲硫基)丙基、4-(甲硫基)丁基、乙硫基甲基、丙硫基甲基、丁硫基甲基、或是戊硫基甲基等之基團。
於本發明中,除非另有特別限定,「C1
~C6
烷基亞磺醯基C1
~C6
烷基」係表示烷基亞磺醯基及烷基為上述意義的(C1
~C6
烷基亞磺醯基)-(C1
~C6
烷基)之基團。
於本發明中,除非另有特別限定,「C1
~C6
烷基磺醯基C1
~C6
烷基」係表示烷基磺醯基部分及烷基部分為上述意義的(C1
~C6
烷基磺醯基)-(C1
~C6
烷基)-基。
於本發明中,除非另有特別限定,「C1
~C6
鹵代烷硫基C1
~C6
烷基」係表示鹵代烷硫基部分及烷基部分為上述意義的(C1
~C6
鹵代烷硫基)-(C1
~C6
烷基)-基。
於本發明中,除非另有特別限定,「C1
~C6
鹵代亞磺醯基C1
~C6
烷基」係表示鹵代亞磺醯基及烷基部分為上述意義的(C1
~C6
鹵代亞磺醯基)-(C1
~C6
烷基)-基。
於本發明中,除非另有特別限定,「C1
~C6
鹵代磺醯基C1
~C6
烷基」係表示鹵代磺醯基及烷基部分為上述意義的(C1
~C6
鹵代磺醯基)-(C1
~C6
烷基)-基。
於本發明中,除非另有特別限定,「C1
~C6
鹵代烷硫基C1
~C6
烷氧基」係表示鹵代烷硫基部分及烷氧基部分為上述意義的(C1
~C6
鹵代烷硫基)-(C1
~C6
烷氧基)之基團。
於本發明中,除非另有特別限定,「C1
~C6
鹵代烷基亞磺醯基C1
~C6
烷氧基」係表示鹵代烷基亞磺醯基及烷氧基部分為上述意義的(C1
~C6
鹵代烷基亞磺醯基)-(C1
~C6
烷氧基)之基團。
於本發明中,除非另有特別限定,「C1
~C6
鹵代烷基磺醯基C1
~C6
烷氧基」係表示鹵代烷基磺醯基及烷氧基部分為上述意義的(C1
~C6
鹵代烷基磺醯基)-(C1
~C6
烷氧基)-基。
於本發明中,除非另有特別限定,「C3
~C6
環烷基C1
~C6
烷硫基」係表示環烷基部分及烷硫基部分為上述意義的(C3
~C6
環烷基)-(C1
~C6
烷硫基)之基團。
於本發明中,除非另有特別限定,「C3
~C6
環烷基C1
~C6
烷基亞磺醯基」係表示環烷基部分及烷基亞磺醯基部分為上述意義的(C3
~C6
環烷基)-(C1
~C6
烷基亞磺醯基)之基團。
於本發明中,除非另有特別限定,「C3
~C6
環烷基C1
~C6
烷基磺醯基」係表示環烷基部分及烷基磺醯基部分為上述意義的(C3
~C6
環烷基)-(C1
~C6
烷基磺醯基)之基團。
於本發明中,除非另有特別限定,「C3
~C6
鹵代環烷基C1
~C6
烷硫基」係表示鹵代環烷基部分及烷硫基部分為上述意義的(C3
~C6
鹵代環烷基)-(C1
~C6
烷硫基)之基團。
於本發明中,除非另有特別限定,「C3
~C6
鹵代環烷基C1
~C6
烷基亞磺醯基」係表示鹵代環烷基部分及烷基亞磺醯基部分為上述意義的(C3
~C6
鹵代環烷基)-(C1
~C6
烷基亞磺醯基)之基團。
於本發明中,除非另有特別限定,「C3
~C6
鹵代環烷基C1
~C6
烷基磺醯基」係表示鹵代環烷基部分及烷基磺醯基部分為上述意義的(C3
~C6
鹵代環烷基)-(C1
~C6
烷基磺醯基)之基團。
於本發明中,除非另有特別限定,「C1
~C6
烷基羰基C1
~C6
烷基」係表示烷基羰基及烷基部分為上述意義的(C1
~C6
烷基羰基)-(C1
~C6
烷基)-基。
於本發明中,除非另有特別限定,「C1
~C6
鹵代烷基羰基C1
~C6
烷基」係表示鹵代烷基羰基及烷基部分為上述意義的(C1
~C6
鹵代烷基羰基)-(C1
~C6
烷基)-基。
於本發明中,除非另有特別限定,「C1
~C6
烷氧基羰基C1
~C6
烷基」係表示烷氧基羰基及烷基部分為上述意義的(C1
~C6
烷氧基羰基)-(C1
~C6
烷基)-基。
於本發明中,「氨基羰基C1
~C6
烷基」係表示NH2
-C(=O)-(C1
~C6
烷基)-基。
於本發明中,「單(C1
~C6
烷基)氨基羰基C1
~C6
烷基」係表示(C1
~C6
烷基)-NH-C(=O)-(C1
~C6
烷基)-基。
於本發明中,「單(C3
~C6
環烷基)氨基羰基C1
~C6
烷基」係表示(C3
~C6
環烷基)-NH-C(=O)-(C1
~C6
烷基)-基。
於本發明中,「單(C1
~C6
鹵代烷基)氨基羰基C1
~C6
烷基」係表示(C1
~C6
鹵代烷基)-NH-C(=O)-(C1
~C6
烷基)-基。
於本發明中,「雙(C1
~C6
烷基)氨基羰基C1
~C6
烷基」係表示(C1
~C6
烷基)2
-N-C(=O)-(C1
~C6
烷基)-基,兩個烷基可彼此不同。
於本發明中,「單(C1
~C6
烷基羰基)氨基C1
~C6
烷基」係表示(C1
~C6
烷基)-C(=O)-NH-(C1
~C6
烷基)-基。
於本發明中,「單(C1
~C6
烷氧基羰基)氨基C1
~C6
烷基」係表示(C1
~C6
烷氧基)-C(=O)-NH-(C1
~C6
烷基)-基。
於本發明中,「單(C1
~C6
烷基磺醯基)氨基C1
~C6
烷基」係表示(C1
~C6
烷基)-S(=O)2
-NH-(C1
~C6
烷基)-基。
於本發明中,「單(C1
~C6
鹵代烷基磺醯基)氨基C1
~C6
烷基」係表示(C1
~C6
鹵代烷基)-S(=O)2
-NH-(C1
~C6
烷基)-基。
於本發明中,「羥基C1
~C6
烷基」係表示HO-(C1
~C6
烷基)-基,意指由「HO-」取代至烷基中任意位置之基團。
於本發明中,「羥基C1
~C6
烷氧基」係表示HO-(C1
~C6
烷氧基)-基,意指由「HO-」取代至烷氧基中任意位置之基團。
於本發明中,「羥基亞氨基C1
~C6
烷基」係表示HO-N=(C1
~C6
烷基)-基,意指由「HO-N=」取代至烷基中任意位置之基團。
於本發明中,「C1
~C6
烷氧基亞氨基C1
~C6
烷基」係表示(C1
~C6
烷氧基)-N=(C1
~C6
烷基)-基,意指由「(C1
~C6
烷氧基)-N=」取代至烷基中任意位置之基團。
於本發明中,「C1
~C6
鹵代烷氧基亞氨基C1
~C6
烷基」係表示(C1
~C6
鹵代烷氧基)-N=(C1
~C6
烷基)-基,意指由「(C1
~C6
鹵代烷氧基)-N=」取代至烷基中任意位置之基團。
於本發明中,除非另有特別限定,「氰基C1
~C6
烷基」係表示烷基部分為上述意義的(氰基)-(C1
~C6
烷基)之基團,可列舉例如氰基甲基、1-氰基乙基、2-氰基乙基、3-氰基丙基、2-氰基丙烷-2-基、1-氰基丁基、4-氰基丁基、5-氰基戊基、或是6-氰基己基之基團。
於本發明中,除非另有特別限定,「氰基C3
~C6
環烷基」係表示環烷基部分為上述意義的(氰基)-(C3
~C6
環烷基)之基團,可列舉例如:1-氰基環丙基、2-氰基環丙基、1-氰基環丁基、2-氰基環丁基、3-氰基環丁基、1-氰基環戊基、3-氰基環戊基、1-氰基環己基、4-氰基環己基等之基團。
於本發明中,除非另有特別限定,「氰基C1
~C6
烷氧基」係表示烷氧基部分為上述意義的(氰基)-(C1
~C6
烷氧基)之基團,可列舉例如:氰基甲氧基、1-氰基乙氧基、2-氰基乙氧基、1-氰基丙氧基、3-氰基丙氧基、2-氰基-2-丙氧基、1-氰基丁氧基、4-氰基丁氧基、5-氰基戊氧基、或是6-氰基己氧基等之基團。
於本發明中,除非另有特別限定,「單(C1
~C6
烷基)氨基」係表示烷基部分為上述意義的(C1
~C6
)烷基-NH-基,可列舉例如甲基氨基、乙基氨基、或是正丙基氨基等之基團。
於本發明中,除非另有特別限定,「雙(C1
~C6
烷基)氨基」係表示烷基部分為上述意義的(C1
~C6
烷基)2
-N-基,兩個烷基可彼此不同,可列舉例如二甲基氨基、甲基乙基氨基、或是甲基正丙基氨基等之基團。
於本發明中,除非另有特別限定,「C1
~C6
烷基羰基氨基」係表示烷基部分為上述意義的(C1
~C6
烷基)-C(=O)-NH-基,可列舉例如:乙醯基氨基、丙醯基氨基、丁醯基氨基、或是異丁醯基氨基等之基團。
於本發明中,除非另有特別限定,「N-(C1
~C6
烷基羰基)-N-(C1
~C6
烷基)氨基」係表示氨基中的兩個氫原子分別被(C1
~C6
烷基)-C(=O)-基及(C1
~C6
烷基)-基所取代之基團,可列舉例如:N-甲基乙醯氨基、N-甲基丙醯基氨基、N-甲基丁醯基氨基、或是N-甲基異丁醯基氨基等之基團。
於本發明中,除非另有特別限定,「C1
~C6
烷氧基羰基氨基」係表示烷氧基部分為上述意義的(C1
~C6
烷氧基)-C(=O)-NH-基,可列舉例如:甲氧基羰基氨基、乙氧基羰基氨基、正丙氧基羰基氨基、或是異丙氧基羰基氨基等之基團。
於本發明中,除非另有特別限定,「C1
~C6
烷氧基羰基羰基氨基」係表示烷氧基部分為上述意義的(C1
~C6
烷氧基)-C(=O)-C(=O)-NH-基。
於本發明中,除非另有特別限定,「N-(C1
~C6
烷氧基羰基)-N-(C1
~C6
烷基)氨基」係表示氨基中的兩個氫原子分別被(C1
~C6
烷氧基)-C(=O)-基及(C1
~C6
烷基)-基所取代的基,可列舉例如:甲氧羰基-(N-甲基)-氨基、乙氧羰基-(N-甲基)-氨基、正丙氧羰基-(N-甲基)-氨基、或異丙氧羰基-(N-甲基)-氨基等之基團。
於本發明中,除非另有特別限定,「N-(C1
~C6
烷氧基羰基羰基)-N-(C1
~C6
烷基)氨基」係表示烷氧基部分及烷基部分為上述意義的[(C1
~C6
烷氧基)-C(=O)-C(=O)][(C1
~C6
烷基)]N之基團。
於本發明中,除非另有特別限定,「N-(C1
~C6
鹵代烷基磺醯基)-N-(C1
~C6
烷基)氨基」係表示鹵代烷基磺醯基部分及烷基部分為上述意義的(C1
~C6
鹵代烷基磺醯基)(C1
~C6
烷基)N之基團。
於本發明中,「氨基羰基氨基」係表示NH2
-C(=O)-NH-基。
於本發明中,「N-(氨基羰基)-N-(C1
~C6
烷基)氨基」係表示NH2
-C(=O)-N(C1
~C6
烷基)-基。
於本發明中,「N-(單(C1
~C6
烷基)氨基羰基)氨基」係表示NH(C1
~C6
烷基)-C(=O)-NH-基。
於本發明中,「N-(單(C1
~C6
烷基)氨基羰基)-N-(C1
~C6
烷基)氨基」係表示NH(C1
~C6
烷基)-C(=O)-N(C1
~C6
烷基)-基。
於本發明中,「N-(雙(C1
~C6
烷基)氨基羰基)氨基」係表示N(C1
~C6
烷基)2
-C(=O)-NH-基,兩個烷基可彼此不同。
於本發明中,「N-(雙(C1
~C6
烷基)氨基羰基羰基)氨基」係表示N(C1
~C6
烷基)2
-C(=O)-C(=O)-NH-基,兩個烷基可彼此不同。
於本發明中,「N-(雙(C1
~C6
烷基)氨基羰基)-N-(C1
~C6
烷基)氨基」係表示N(C1
~C6
烷基)2
-C(=O)-N(C1
~C6
烷基)-基,兩個烷基可彼此不同。
於本發明中,「N-(雙(C1
~C6
烷基)氨基羰基羰基)-N-(C1
~C6
烷基)氨基」係表示N(C1
~C6
烷基)2
-C(=O)-C(=O)-N(C1
~C6
烷基)-基,兩個烷基可彼此不同。
於本發明中,「氨基(硫代羰基)氨基」係表示NH2
-C(=S)-NH-。
於本發明中,「N-(雙(C1
~C6
烷基)氨基(硫代羰基))氨基」係表示N(C1
~C6
烷基)2
-C(=S)-NH-基,兩個烷基可彼此不同。
於本發明中,「N-(雙(C1
~C6
烷基)氨基(硫代羰基))-N-(C1
~C6
烷基)氨基」係表示N(C1
~C6
烷基)2
-C(=S)-N(C1
~C6
烷基)-基,兩個烷基可彼此不同。
於本說明書中,「碳環」係意指芳族或非芳族的單環或多環,且構成環的原子全部都是碳原子。
於一態樣中,作為碳環的示例,包含芳族或非芳族的單環、二環或三環的3~14元(較佳為4~14元,更佳為5~14元,特佳為5~10元,最佳為6~10元)的環,惟並不限於此。
於另一態樣中,碳環係包含芳族或非芳族的單環或雙環(較佳為單環)的4~8元(較佳為5~6元)的環,惟並不限於此。
碳環的示例包含環戊烷、環己烷、環戊烯、環己烯、苯等,惟並不限於此。
於本說明書中,「雜環」係具有1個以上相同或不同的雜原子(例如氮原子、氧原子及/或硫原子),以替代1個以上的碳原子的芳族或是非芳族的單環或多環的環。
作為一態樣,雜環的示例包括芳族或非芳族的單環、雙環或三環的3~14元(較佳為4~14元,更佳為5~14元)的雜環,且其中包含具有1~13個碳原子,以及獨立地選自氮原子、氧原子及硫原子之1~4個雜原子,惟並不限於此。
作為另一態樣,雜環的示例包括芳族或非芳族的單環或雙環的3~10元(較佳為4~10元,更佳為5~10元,最佳為5~7元)的雜環,且其中包含具有1~9個碳原子,以及獨立地選自氮原子、氧原子及硫原子的1~4個雜原子,惟並不限於此。
於又一實施態樣中,雜環的示例包括芳族或非芳族的單環的4~8元(較佳為5~6元)的雜環,且其中包含具有1~5個碳原子,以及獨立地選自氮原子、氧原子及硫原子的1~4個雜原子,惟並不限於此。
單環的雜環的具體示例包括:噻吩、吡咯、咪唑、三唑、呋喃、四氫噻吩、吡咯烷、四氫呋喃、吡啶、吡嗪、噠嗪、嘧啶、噻唑、吡喃、呱啶、四氫吡喃、噻吩、呱嗪、嗎啉、硫嗎啉、二噁烷、二噻烷等,惟並不限於此。
雙環的雜環的具體示例包括:喹啉、苯並噻吩、吲哚、苯並呋喃、苯並咪唑等,惟並不限於此。
三環的雜環的具體示例包括:丙烯酸酯、二苯並噻吩、哢唑(carbazole)、二苯並呋喃,惟並不限於此。
於本發明中,除非另有特別限定,「C1
~C6
烷基磺醯基氨基」係表示烷基部分為上述意義的(C1
~C6
烷基)-S(=O)2
-NH-基,可列舉例如:甲基磺醯基氨基、乙基磺醯基氨基、正丙基磺醯基氨基、異丙基磺醯基氨基、或是叔丁基磺醯基氨基等之基團。
於本發明中,除非另有特別限定,「C1
~C6
鹵代烷基磺醯基氨基」係表示鹵代烷基部分為上述意義的(C1
~C6
鹵代烷基)-S(=O)2
-NH-基,可列舉例如:二氟甲基磺醯基氨基、三氟甲基磺醯基氨基、三氯甲基磺醯基氨基、2,2,2-三氟乙基磺醯基氨基、五氟乙基磺醯基氨基、3,3,3-三氟丙基磺醯基氨基、七氟丙基磺醯氨基、或是七氟-2-丙基磺醯氨基等之基團。
於本發明中,「雙(C1
~C6
烷基磺醯基)氨基」係表示N(C1
~C6
烷基磺醯基)2
-基,兩個烷基磺醯基可彼此不同。
於本發明中,「雙(C1
~C6
鹵代烷基磺醯基)氨基」係表示N(C1
~C6
鹵代烷基磺醯基)2
-基,兩個鹵代烷基磺醯基可彼此不同。
於本發明中,除非另有特別限定,「N(C1
~C6
烷基磺醯基)-N-(C1
~C6
烷基)氨基」係表示氨基中的兩個氫原子分別被(C1
~C6
烷基)-S(=O)2
-基及(C1
~C6
烷基)-基所取代的基,可列舉例如:N-甲基甲基磺醯基氨基、N-甲基乙基磺醯基氨基、N-甲基-正丙基磺醯基氨基、N-甲基異丙基磺醯基氨基、或是N-甲基叔丁基磺醯基氨基等之基團。
於本發明中,「氨基磺醯基氨基」係表示NH2
-S(=O)2
-NH-基。
於本發明中,「N-(氨基磺醯基)-N-(C1
~C6
烷基)氨基」係表示NH2
-S(=O)2
-N(C1
~C6
烷基)-基。
於本發明中,「N-(單(C1
~C6
烷基)氨基磺醯基)氨基」係表示NH(C1
~C6
烷基)-S(=O)2
-NH-基。
於本發明中,「N-(單(C1
~C6
烷基)氨基磺醯基-N-(C1
~C6
烷基)氨基」係表示NH(C1
~C6
烷基)-S(=O)2
-N(C1
~C6
烷基)-基。
於本發明中,「N-(雙(C1
~C6
烷基)氨基磺醯基)氨基」係表示N(C1
~C6
烷基)2
-S(=O)2
-NH-基,兩個烷基可彼此不同。
於本發明中,「N-(雙(C1
~C6
烷基)氨基磺醯基)-N-(C1
~C6
烷基)氨基」係表示N(C1
~C6
烷基)2
-S(=O)2
-N(C1
~C6
烷基)-基,兩個烷基可彼此不同。
於本發明中,「(雙(C1
~C6
烷基)亞硫烷基)氨基」係表示O=S(C1
~C6
烷基)2-=N-基,兩個烷基可彼此不同,可列舉例如:(S,S-二甲基亞硫烷基)氨基、(S,S-二乙基亞硫烷基)氨基、(S-乙基-S-甲基亞硫烷基)氨基等之基團。
於本發明中,除非另有特別限定,「C1
~C7
醯基)」係表示H-C(=O)基或是(C1
~C6
烷基)-C(=O)之基團,可列舉例如:甲醯基、乙醯基、丙醯基、異丁醯基、或是新戊醯基等之基團。
於本發明中,除非另有特別限定,「C1
~C7
鹵代醯基)」係表示由鹵素取代的甲醯基或是(C1
~C6
鹵代醯基)-C(=O)之基團,可列舉例如:氯甲醯基、氯乙醯基、2-氯丙醯基、2-氯異丁醯基、或是3-氯新戊醯基等之基團。
於本發明中,「羥基亞氨基(氨基)C1
~C7
烷基)」係表示(H2
N)C(=NOH)之基團或是(H2
N)C=(NOH)-(C1
~C6
烷基)-基。
於本發明中,「羧基」係表示HO-C(=O)-基。
於本發明中,「C1
~C6
烷氧基羰基」係表示(C1
~C6
烷氧基)-C(=O)-基。
於本發明中,「N-(C1
~C6
烷氧基)-N-(C1
~C6
烷基)氨基羰基」係表示(C1
~C6
烷氧基)(C1
~C6
烷基)N-C(=O)-基。
於本發明中,「氨基羰基」係表示NH2
-C(=O)-基。
於本發明中,「氨基硫代羰基」係表示NH2
-C(=S)-基。
於本發明中,除非另有特別限定,「單(C1
~C6
)烷基氨基羰基」係表示烷基部分為上述意義的(C1
~C6
烷基)-NH-C(=O)-基,可列舉例如:甲基氨基羰基、乙基氨基羰基、丙基氨基羰基、或是異丙基氨基羰基等之基團。
於本發明中,除非另有特別限定,「單(C1
~C6
烷基)氨基硫代羰基」係表示烷基部分為上述意義的(C1
~C6
烷基)-NH-C(=S)-基。
於本發明中,除非另有特別限定,「單(C1
~C6
)烷基氨基羰基」係表示烷基部分為上述意義的(C1
~C6
烷基)2
-N-C(=O)-基,兩個烷基可彼此不同,可列舉例如:二甲基氨基羰基、二乙基氨基羰基、或是二異丙基氨基羰基
等之基團。
於本發明中,除非另有特別限定,「雙(C1
~C6
烷基)氨基硫代羰基」係指烷基部分為上述意義的(C1
~C6
烷基)2
-N-C(=S)-基,兩個烷基可彼此不同。
於本發明中,除非另有特別限定,「單(C1
~C6
鹵代烷基)氨基羰基」係指鹵代烷基部分為上述意義的(C1
~C6
鹵代烷基)-NH-C(=O)-基,可列舉例如:2-氟乙基氨基羰基、2,2,2-三氟乙基氨基羰基、2,2,2-三氯乙基氨基羰基、或是1,1,1,3,3,3-六氟-2-丙基氨基羰基等之基團。
於本發明中,除非另有特別限定,「單(C3
~C6
環烷基)氨基羰基」係表示環烷基部分為上述意義的(C3
~C6
環烷基)-NH-C(=O)-基,可列舉例如:環丙基氨基羰基、環丁基氨基羰基、環戊基氨基羰基、環己基氨基羰基等之基團。
於本發明中,除非另有特別限定,「雙(C3
~C6
環烷基)氨基羰基」係表示環烷基部分為上述意義的(C3
~C6
環烷基)2
-N-C(=O)-基,可列舉例如:二(環丙基)氨基羰基、二(環丁基)氨基羰基、二(環戊基)氨基羰基、二(環己基)氨基羰基等之基團。
於本發明中,「(C1
~C6
烷氧基)(C1
~C6
烷基)氨基羰基」係表示(C1
~C6
烷氧基)-(C1
~C6
烷基)-NH-C(=O)-基。
於本發明中,除非另有特別限定,「(C1
~C6
鹵代烷基)(單(C1
~C6
鹵代烷基)氨基羰基)氨基羰基」係表示鹵代烷基部分為上述意義的(C1
~C6
鹵代烷基)-NH-C(=O)-N(C1
~C6
鹵代烷基)-C(=O)-基,可列舉例如:N-(2,2,2-三氟乙基)-N-(2,2,2-三氟乙基氨基羰基)氨基羰基等之基團。
於本發明中,除非另有特別限定,「(C1
~C6
鹵代烷基)(C1
~C6
鹵代烷基亞氨基C1
~C6
鹵代烷基)氨基羰基」係表示鹵代烷基部分為上述意義的(C1
~C6
鹵代烷基)-N=(C1
~C6
鹵代烷基)-N(C1
~C6
鹵代烷基)-C(=O)-基,可列舉例如:N-(2,2,2-三氟乙基)-N-(1-氯-1-(2,2,2-三氟乙基亞氨基)甲基)氨基羰基之基團。
於本發明中,「未取代、或是由R11
任意取代的C6
~C12
芳基」等記載係表示與碳原子鍵合的氫原子被任意的R11
所取代的芳基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的芳基上的取代基R11
時,各個R11
可彼此相同或彼此不同。
於本發明中,「未取代、或是由R11
任意取代的C5
~C12
雜芳基」等記載係表示與碳原子鍵合的氫原子被任意的R11
所取代的雜芳基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的雜芳基上的取代基R11
時,各個R11
可彼此相同或彼此不同。
於本發明中,「未取代、或是由R11
任意取代的C7
~C1 4
芳烷基」等記載係表示與碳原子鍵合的氫原子被任意的R11
所取代的芳烷基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的芳烷基上的取代基R11
時,各個R11
可彼此相同或是彼此不同。
於本發明中,「未取代、或是由R11
任意取代的C6
~C12
雜芳烷基」等記載,係表示與碳原子鍵合的氫原子被任意的R11
所取代的雜芳烷基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的雜芳烷基上的取代基R11
時,各個R11
可彼此相同或是彼此不同。
於本發明中,「未取代、或是由R11
任意取代的C6
~C12
芳氧基」等記載,係表示與碳原子鍵合的氫原子被任意的R11
所取代的芳氧基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的芳氧基上的取代基R11
時,各個R11
可彼此相同或是彼此不同。
於本發明中,「未取代、或是由R11
任意取代的C5
~C12
雜芳氧基」等記載,係表示與碳原子鍵合的氫原子被任意的R11
所取代的雜芳氧基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的雜芳氧基上的取代基R11
時,各個R11
可彼此相同或是彼此不同。
於本發明中,「未取代、或是由R11
任意取代的C7
~C1 4
芳烷氧基」等記載,係表示與碳原子鍵合的氫原子被任意的R11
所取代的芳烷氧基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的芳烷氧基上的取代基R11
時,各個R11
可彼此相同或是彼此不同。
於本發明中,「未取代、或是由R11
任意取代的C6
~C12
雜芳烷氧基」等記載,係表示與碳原子鍵合的氫原子被任意的R11
所取代的雜芳烷氧基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的雜芳烷氧基上的取代基R11
時,各個R11
可彼此相同或是彼此不同。
於本發明中,「未取代、或是由R11
任意取代的雜環基」等記載,係表示與碳原子鍵合的氫原子被任意的R11
所取代的雜環基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的雜環基上的取代基R11
時,各個R11
可彼此相同或是彼此不同。
於本發明中,雜環基係意指芳族或非芳族的單環或多環的環形基,且其中具有一個以上的相同或不同的雜原子(例如氮原子、氧原子及/或硫原子)來替代一個以上的碳原子。
於本發明中,雜環基的示例包括芳族或非芳族的單環、雙環或是三環的3~14元(較佳為4~14元,更佳為5~14元)的雜環基,且其中具有1~13個碳原子,以及獨立地選自氮原子、氧原子及硫原子之1~4個雜原子,惟並不限於此。
於本發明中,雜環基的示例包括芳族或非芳族的單環或雙環的3~10元(較佳為4~10元,更佳為5~10元,最佳為5~7元)的雜環基,且其中具有1~9個碳原子,以及獨立地選自氮原子、氧原子及硫原子之1~4個雜原子,惟並不限於此。
進一步地,於本發明中,雜環基的示例包括芳族或非芳族的單環的4~8元(較佳為5~6元)的雜環基,且其中具有1~5個碳原子,以及獨立地選自氮原子、氧原子及硫原子之1~4個雜原子,惟並不限於此。
單環的雜環基的具體示例包括:吡咯基、呋喃基、噻吩基、吡唑基、咪唑基、噁唑基、異噁唑基、噻唑基、異噻唑基、三唑基、惡二唑基(例如1,2,4-惡二唑基、1,2,5-惡二唑基)、噻二唑基(例如1,2,3-噻唑基、1,3,4-噻二唑基等)、四唑基、吡啶基、噠嗪基、嘧啶基、吡嗪基、三嗪基(例如1,3,5-三嗪基等)、呱啶基、呱嗪基、嗎啉基等,惟並不限於此。
雙環的雜環基的具體示例包括:吲哚基(indolyl)、異吲哚基、咪嗪基(indolizinyl)、苯並呋喃基、苯並噻吩基、苯並咪唑基、吲唑基、苯並噁唑基、苯並異噁唑基、苯並噻唑基、苯並異噻唑基、喹啉基、異喹啉基、喹啉基、辛啉基、喹咢啉基(quinoxalinyl)、喹唑啉基(quinazolinyl)、呔嗪基(phthalazinyl)、萘啶基(Naphthyridinyl)(例如1,5-萘啶基、1,6-萘啶基、1,7-萘啶基、1,8萘啶基、2,6-萘啶基、2,7-萘啶基)、吲哚啉基(indolinyl)、異吲哚啉基、苯並二氫呱喃基(chromanyl)、異苯並二氫萘基、香豆素基(coumarinyl)、異香豆素基、苯並三嗪基、四氫異喹啉基、吡啶吡啶基(pyrid pyridyl)、吡啶吡唑基(pyrid pyrazyl)、異苯並噻吩基、苯並四氫呋喃基、苯並四氫噻吩基、異苯並四氫呋喃基、異苯並四氫噻吩基、嘌呤基(purinyl)、苯並二噁唑基、苯惡丁啶基、吩噻啶基、蝶啶基(pteridinyl)、噁唑基吡啶基、咪唑並吡啶基、咪唑並噻唑基、二氫苯並異惡嗪基、苯並惡嗪基、苯並異惡嗪基、二氫苯並異噻啶基、苯並吡喃基、苯並硫代吡喃基、色酮基(chromonyl)、色滿基(chromanonyl)、吡啶基-N-氧化物四氫喹啉基、二氫喹啉基、二氫喹啉酮基、二氫異喹啉酮基、二氫香豆素基(Dihydrocoumarinyl)、二氫異香豆素基(Dihydroisocoumarinyl)、異吲哚啉基、苯並二噁烷基、苯並噁唑啉基等,惟並不限於此。
三環的雜環基的具體示例包括:哢唑基、β-哢啉基、吖啶基(acridinyl)、啡啶基(phenanthridinyl)、啡啉基(phenanthrolinyl)(例如4,7-啡啉基、1,10-啡啉基等)、吩嗪基(phenazinyl),惟並不限於此。
於此,取代位置並無特別限定。也就是說,雜環基包括所有其位置異構體。例如,當雜環基為吡啶基時,吡啶基包括:2-吡啶基、3-吡啶基以及4-吡啶基。
若情況允許,如上所定義或是示例的雜環基可包括非縮合環(例如單環或是螺環)及縮合環的環形基。
若情況允許,如上所定義或是示例的雜環基可為不飽和、部分飽和或是飽和中的任一者。
於本說明書中,如上所定義或是示例的雜環基也可稱為異環基(heterocyclyl)。
當如上所定義或是示例的雜環基的雜原子為氮原子時,氮原子可為N-氧化物。
當如上所定義或是示例的雜環基的雜原子為硫原子時,硫原子可為亞磺醯基(-SO-)或是磺醯基(-SO2
-)。
於本發明中,「未取代、或是由R11
任意取代的C6
~C12
芳基羰基」等記載,係表示與碳原子鍵合的氫原子被任意的R11
取代的芳基羰基,取代的R11
的數目可在各個指定的碳原子數目範圍內任意選擇。當存在有兩個以上的芳基羰基上的取代基R11
時,各個R11
可彼此相同或彼此不同。
於本發明中,農業上可允許的鹽係為通式[I]所示本發明之化合物中,於其結構中存在有羥基、羧基、或是氨基等時,其與金屬或是有機鹼的鹽;或是與無機酸或有機酸的鹽,其中金屬可列舉鈉或鉀等之鹼金屬、或是鎂或鈣等之鹼土金屬;有機鹼可列舉三乙胺、或是二異丙胺等;無機酸可列舉鹽酸、氫溴酸或是硫酸等,另外,有機酸可列舉甲酸、乙酸、甲磺酸、4-甲苯磺酸、或是三氟甲磺酸等。
於一實施態樣中,本發明提供通式(A)所示的化合物。
(A)
式中,n, R4
, R8
, R9
及R1 0
係表示與上述相同的意義。較佳地,n為2,且R4
係為C1
~C6
鹵代烷基、C1
~C6
鹵代烷氧基、或是未取代或由R11
任意取代的雜環基
,R8
及R9
係為分別獨立的氫原子或是鹵素原子,R1 0
係為C1
~C6
鹵代烷基。通式(A)所示化合物係示例於表1~表150中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(B)所示的化合物。
(B)
式中,n, R3
, R5
, R6
, R8
, R9
及R1 0
係表示與上述相同的意義。通式(B)所示化合物係示例於表151~表186中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(C)所示的化合物。
(C)
式中,n, R3
, R4
, R5
, R6
, R8
, R9
及R1 0
係表示與上述相同的意義。通式(C)所示化合物係示例於表187~表198中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(D)所示的化合物。
(D)
式中,R3
, R4
, R5
, R6
, R8
及R9
係表示與上述相同的意義。通式(D)所示化合物係示例於表199~表221中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(E)所示的化合物。
(E)
式中,m, n, R1
, R2
, R4
, R5
, R8
, R9
及R1 0
係表示與上述相同的意義。通式(E)所示化合物係示例於表222~表245中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(F)所示的化合物。
(F)
式中,n, R2
, R4
, R5
, R8
, R9
及R1 0
係表示與上述相同的意義。通式(F)所示化合物係示例於表246~表322中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(G)所示的化合物。
(G)
式中,n, R2
, R4
, R8
, R9
及R1 0
係表示與上述相同的意義。通式(G)所示化合物係示例於表323~表346中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(H)所示的化合物。
(H)
式中,n, R2
, R5
, R6
, R8
, R9
及R1 0
係表示與上述相同的意義。通式(H)所示化合物係示例於表347~表358中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(I)所示的化合物。
(I)
式中,n, R2
, R4
, R5
,R8
, R9
及R1 0
係表示與上述相同的意義。通式(I)所示化合物係示例於表359~表373中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(J)所示的化合物。
(J)
式中,n, A3
, A4
, A5
, A6
, R2
, R8
, R9
及R1 0
係表示與上述相同的意義。通式(J)所示化合物係示例於表374~表402中,惟不限於此等化合物。
於一實施態樣中,本發明提供通式(K)所示的化合物。
(K)
式中,n, A6
, A7
, A8
, A9
, R2
, R4
及R1 0
係表示與上述相同的意義。通式(K)所示化合物係示例於表403~表452中,惟不限於此等化合物。
接著,表1至表452係示出了通式[I]所示本發明之唑衍生物中所含的化合物之代表性化合物的示例。然而,本發明之衍生物中所含的化合物並不限於此。此外,於之後的記載係參照表內的化合物編號。
另外,根據取代基的種類,本發明之唑衍生物中所含的化合物中會有E型及Z型的幾何異構體存在的情況,而本發明並包括了含有此等E型、Z型以及以任意比例含有E型及Z型的混合物。另外,本發明中所含的化合物係可能會有由一個或是兩個以上的不對稱碳原子及不對稱硫原子之存在所導致光學異構體存在的情況,而本發明包括所有的光學活性物質、外消旋體、或是非鏡像異構物。
於本說明書中的表中的下述標示係表示相應之基團,例如以下所述。
Me:甲基
Et:乙基
nPr:正丙基
iPr:異丙基
cPr:環丙基
nBu:正丁基
sBu:仲丁基
iBu:異丁基
tBu:叔丁基
cBu:環丁基
nPen:正戊基
cPen:環戊基
nHex:正己基
cHex:環己基
(1-CN)cPr:1-氰基環丙基
(2,2-F2
)cPr:2,2-二氟環丙基
PH:苯基
3-Py:3-吡啶基
(4-CF3
)Ph:4-三氟甲基苯基
(2-F-4-CF3
)Ph:2-氟-4-三氟甲基苯基
(3-Cl)(5-CF3
)2
-Py:3-氯-5-三氟甲基-2-吡啶基
[表1]
[表2]
[表3]
[表4]
[表5]
[表6]
[表7]
[表8]
[表9]
[表10]
[表11]
[表12]
[表13]
[表14]
[表15]
[表16]
[表17]
[表18]
[表19]
[表20]
[表21]
[表22]
[表23]
[表24]
[表25]
[表26]
[表27]
[表28]
[表29]
[表30]
[表31]
[表32]
[表33]
[表34]
[表35]
[表36]
[表37]
[表38]
[表39]
[表40]
[表41]
[表42]
[表43]
[表44]
[表45]
[表46]
[表47]
[表48]
[表49]
[表50]
[表51]
[表52]
[表53]
[表54]
[表55]
[表56]
[表57]
[表58]
[表59]
[表60]
[表61]
[表62]
[表63]
[表64]
[表65]
[表66]
[表67]
[表68]
[表69]
[表70]
[表71]
[表72]
[表73]
[表74]
[表75]
[表76]
[表77]
[表78]
[表79]
[表80]
[表81]
[表82]
[表83]
[表84]
[表85]
[表86]
[表87]
[表88]
[表89]
[表90]
[表91]
[表92]
[表93]
[表94]
[表95]
[表96]
[表97]
[表98]
[表99]
[表100]
[表101]
[表102]
[表103]
[表104]
[表105]
[表106]
[表107]
[表108]
[表109]
[表110]
[表111]
[表112]
[表113]
[表114]
[表115]
[表116]
[表117]
[表118]
[表119]
[表120]
[表121]
[表122]
[表123]
[表124]
[表125]
[表126]
[表127]
[表128]
[表129]
[表130]
[表131]
[表132]
[表133]
[表134]
[表135]
[表136]
[表137]
[表138]
[表139]
[表140]
[表141]
[表142]
[表143]
[表144]
[表145]
[表146]
[表147]
[表148]
[表149]
[表150]
[表151]
[表152]
[表153]
[表154]
[表155]
[表156]
[表157]
[表158]
[表159]
[表160]
[表161]
[表162]
[表163]
[表164]
[表165]
[表166]
[表167]
[表168]
[表169]
[表170]
[表171]
[表172]
[表173]
[表174]
[表175]
[表176]
[表177]
[表178]
[表179]
[表180]
[表181]
[表182]
[表183]
[表184]
[表185]
[表186]
[表187]
[表188]
[表189]
[表190]
[表191]
[表192]
[表193]
[表194]
[表195]
[表196]
[表197]
[表198]
[表199]
[表200]
[表201]
[表202]
[表203]
[表204]
[表205]
[表206]
[表207]
[表208]
[表209]
[表210]
[表211]
[表212]
[表213]
[表214]
[表215]
[表216]
[表217]
[表218]
[表219]
[表220]
[表221]
[表222]
[表223]
[表224]
[表225]
[表226]
[表227]
[表228]
[表229]
[表230]
[表231]
[表232]
[表233]
[表234]
[表235]
[表236]
[表237]
[表238]
[表239]
[表240]
[表241]
[表242]
[表243]
[表244]
[表245]
[表246]
[表247]
[表248]
[表249]
[表250]
[表251]
[表252]
[表253]
[表254]
[表255]
[表256]
[表257]
[表258]
[表259]
[表260]
[表261]
[表262]
[表263]
[表264]
[表265]
[表266]
[表267]
[表268]
[表269]
[表270]
[表271]
[表272]
[表273]
[表274]
[表275]
[表276]
[表277]
[表278]
[表279]
[表280]
[表281]
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[表294]
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[表296]
[表297]
[表298]
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[表300]
[表301]
[表302]
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[表305]
[表306]
[表307]
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[表310]
[表311]
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[表314]
[表315]
[表316]
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[表318]
[表319]
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[表323]
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[表328]
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[表333]
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[表335]
[表336]
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[表339]
[表340]
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[表342]
[表343]
[表344]
[表345]
[表346]
[表347]
[表348]
[表349]
[表350]
[表351]
[表352]
[表353]
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[表356]
[表357]
[表358]
[表359]
[表360]
[表361]
[表362]
[表363]
[表364]
[表365]
[表366]
[表367]
[表368]
[表369]
[表370]
[表371]
[表372]
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[表374]
[表375]
[表376]
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[表436]
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[表441]
[表442]
[表443]
[表444]
[表445]
[表446]
[表447]
[表448]
[表449]
[表450]
[表451]
[表452]
另一方面,通式[I]所示的本發明化合物可根據以下所示製造方法來製造,惟並不限於此等方法。另外,於下文中,例如「通式[I]所示化合物」、「通式[I]所示化合物」及「化合物[I]」係為相同意義。
<製造方法1>
於本發明化合物中,通式[IV]所示化合物可根據例如以下方法製造。
(式中,X係表示鹵素原子、C1
~C6
烷基磺醯基、C1
~C6
鹵代烷基磺醯基、可取代的C6
~C12
芳基磺醯基、C1
~C6
烷基磺醯氧基、C1
~C6
鹵代烷基磺醯氧基、可取代的C6
~C12
芳基磺醯氧基、C1
~C6
烷基羰氧基,m, n, R1
, R2
, A3
, A4
, A5
, A6
, A7
, A8
, A9
及R1 0
係表示與上述相同的意義。)
即,可透過在適當的溶劑中且存在或是不存在適當的鹼的情況下,使通式[II]所示化合物與通式[III]所示化合物反應,而製造出通式[IV]所示化合物。
相對於化合物[II]1莫耳,於本反應中所使用的化合物[III]的使用量通常可由1~100莫耳範圍內適當選擇,較佳為1~5莫耳。
於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[II]1莫耳,鹼的使用量可由0~5莫耳範圍內適當選擇,較佳為0.1~2莫耳。
作為可於本反應中使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[II]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
本反應可依所需而在催化劑的存在下進行。催化劑係包含金屬或金屬鹽,以及作為配位體的化合物。所述催化劑係可於反應體系中(原位(in situ))而自後述的金屬或金屬鹽以及作為配位體的化合物來調製,亦可事先於反應體系外調製再加入至反應體系中。催化劑可包含金屬、金屬鹽及作為配位體的化合物以外的成分。金屬或金屬鹽可列舉例如:如金屬銅、乙酸銅(一價)、乙酸銅(二價)、氧化銅(一價)、氧化銅(二價)、氯化銅(一價)、碘化銅(一價)等之銅化合物;如碳鈀、氯化鈀、硝酸鈀、乙酸鈀、雙(三苯基苯基膦)二氯化鈀、四(三苯基苯基膦)鈀等之鈀化合物。配位體可列舉乙二胺、N,N-二甲基乙二胺、N,N'-二甲基乙二胺、四甲基乙二胺、2,2'-聯吡啶、1,10-菲咯啉、2,9-二甲基-1,10-菲囉啉(neocuproine)、3,4,7,8-四甲基-1,10-菲咯啉、2,9-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、三苯基膦、1,1'-雙(二苯基膦基)二茂鐵等及此等的鹽等。關於金屬或金屬鹽及配位體的組合,可由其中的作為配位體的化合物相對於金屬或金屬鹽1莫耳係為0.1~10莫耳範圍內適當選擇,較佳為1~4莫耳。此外,關於催化劑的使用量,可由其中的金屬或金屬鹽相對於化合物[II]1莫耳係為0.001~10莫耳範圍內適當選擇,較佳為0.01~5莫耳。
本反應的反應溫度可由-78℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於0℃~180℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~48小時。
反應結束後,可藉由進行將反應混合物注入水中,並且濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[IV]。分離出的化合物[IV]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法2>
本發明化合物當中,通式[IV]所示化合物係可根據例如以下方法來製造。
(式中,X, m, n, R1
, R2
, A3
, A4
, A5
, A6
, A7
, A8
, A9
及R1 0
表示與上述相同的意義。)
即,可透過在適當的溶劑中且存在或是不存在適當的鹼的情況下,使通式[V]所示化合物與通式[VI]所示化合物反應,而製造出通式[IV]所示化合物。
相對於化合物[V]1莫耳,於本反應中所使用的化合物[VI]的使用量通常可由1~100莫耳範圍內適當選擇,較佳為1~5莫耳。
於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[V]1莫耳,鹼的使用量可由0~5莫耳範圍內適當選擇,較佳為0.1~2莫耳。
作為可於本反應中使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[V]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
本反應可依所需而在催化劑的存在下進行。催化劑係包含金屬或金屬鹽,以及作為配位體的化合物。所述催化劑係可於反應體系中(原位(in situ))而自後述的金屬或金屬鹽以及作為配位體的化合物來調製,亦可事先於反應體系外調製再加入至反應體系中。催化劑可包含金屬、金屬鹽及作為配位體的化合物以外的成分。金屬或金屬鹽可列舉例如:如金屬銅、乙酸銅(一價)、乙酸銅(二價)、氧化銅(一價)、氧化銅(二價)、氯化銅(一價)、碘化銅(一價)等之銅化合物;如碳鈀、氯化鈀、硝酸鈀、乙酸鈀、雙(三苯基苯基膦)二氯化鈀、四(三苯基苯基膦)鈀等之鈀化合物。配位體可列舉乙二胺、N,N-二甲基乙二胺、N,N'-二甲基乙二胺、四甲基乙二胺、2,2'-聯吡啶、1,10-菲咯啉、2,9-二甲基-1,10-菲囉啉(neocuproine)、3,4,7,8-四甲基-1,10-菲咯啉、2,9-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、三苯基膦、1,1'-雙(二苯基膦基)二茂鐵等及此等的鹽等。關於金屬或金屬鹽及配位體的組合,可由其中的作為配位體的化合物相對於金屬或金屬鹽1莫耳係為0.1~10莫耳範圍內適當選擇,較佳為1~4莫耳。此外,關於催化劑的使用量,可由其中的金屬或金屬鹽相對於化合物[V]1莫耳係為0.001~10莫耳範圍內適當選擇,較佳為0.01~5莫耳。
本反應的反應溫度可由-78℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於0℃~180℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~48小時。
反應結束後,可藉由進行將反應混合物注入水中,並且濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[IV]。分離出的化合物[IV]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法3>
本發明化合物當中,通式[X]所示化合物係可根據例如以下方法來製造。
(式中,R1 2
係表示氫原子、鹵素原子、C1
~C6
鹵代烷基、C1
~C6
鹵代烷氧基;R1 0
’係表示R1 0
當中氫以外的取代基;X, m, n, R1
, R2
, A3
, A4
, A5
, A6
, A7
, A8
及A9
表示與上述相同的意義。)
即,可透過在適當的溶劑中且存在或是不存在適當的鹼的情況下,使通式[VII]所示化合物與化合物[VIII]或是化合物[IX]所示化合物反應,而製造出通式[X]所示化合物。
相對於化合物[VII]1莫耳,於本反應中所使用的化合物[VIII]或是化合物[IX]的使用量通常可由1~10莫耳範圍內適當選擇,較佳為1~2莫耳。
於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;如甲氧基鈉、乙氧基鈉、叔丁醇鉀等之醇的金屬鹽類;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[VII]1莫耳,鹼的使用量可由0~10莫耳範圍內適當選擇,較佳為0~5莫耳。
作為可於本反應中使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[VII]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
本反應的反應溫度可由-78℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於0℃~100℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~24小時。
反應結束後,可藉由在將反應混合物注入水中或是濃縮等操作之後,進行濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[X]。分離出的化合物[X]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法4>
本發明化合物當中,通式[IV]所示化合物亦可根據例如以下方法來製造。
(式中,X, m, n, R1
, R2
, A3
, A4
, A5
, A6
, A7
, A8
, A9
及R1 0
表示與上述相同的意義。)
即,可透過在適當的溶劑中且存在或是不存在適當的鹼的情況下,使通式[XI]所示化合物與通式[XII]所示化合物反應,而製造出通式[IV]所示化合物。
相對於化合物[XI]1莫耳,於本反應中所使用的化合物[XII]的使用量通常可由1~5莫耳範圍內適當選擇,較佳為1~1.5莫耳。
於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;如甲氧基鈉、乙氧基鈉、叔丁醇鉀等之醇的金屬鹽類;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[XI]1莫耳,鹼的使用量可由0~5莫耳範圍內適當選擇,較佳為0.1~2莫耳。
作為可於本反應中使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[XI]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
本反應可依所需而在催化劑的存在下進行。催化劑係包含金屬或金屬鹽,以及作為配位體的化合物。所述催化劑係可於反應體系中(原位(in situ))而自後述的金屬或金屬鹽以及作為配位體的化合物來調製,亦可事先於反應體系外調製再加入至反應體系中。催化劑可包含金屬、金屬鹽及作為配位體的化合物以外的成分。金屬或金屬鹽可列舉例如:如金屬銅、乙酸銅(一價)、乙酸銅(二價)、氧化銅(一價)、氧化銅(二價)、氯化銅(一價)、碘化銅(一價)等之銅化合物;如碳鈀、氯化鈀、硝酸鈀、乙酸鈀、雙(三苯基苯基膦)二氯化鈀、四(三苯基苯基膦)鈀等之鈀化合物。配位體可列舉乙二胺、N,N-二甲基乙二胺、N,N'-二甲基乙二胺、四甲基乙二胺、2,2'-聯吡啶、1,10-菲咯啉、2,9-二甲基-1,10-菲囉啉(neocuproine)、3,4,7,8-四甲基-1,10-菲咯啉、2,9-二苯基-1,10-菲咯啉、4,7-二苯基-1,10-菲咯啉、三苯基膦、1,1'-雙(二苯基膦基)二茂鐵等及此等的鹽等。關於金屬或金屬鹽及配位體的組合,可由其中的作為配位體的化合物相對於金屬或金屬鹽1莫耳係為0.1~10莫耳範圍內適當選擇,較佳為1~4莫耳。此外,關於催化劑的使用量,可由其中的金屬或金屬鹽相對於化合物[XI]1莫耳係為0.001~10莫耳範圍內適當選擇,較佳為0.01~5莫耳。
本反應的反應溫度可由0℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於20℃~180℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~24小時。
反應結束後,可藉由在將進行反應混合物注入水中,並濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[IV]。分離出的化合物[IV]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法5>
本發明化合物當中,通式[XV]所示化合物可根據例如以下方法來製造。
(式中,m, n, R1
, R2
, A3
, A4
, A5
, A6
, R8
, R9
及R1 0
表示與上述相同的意義。)
即,可透過在適當的溶劑中且存在或是不存在適當的鹼或是適當的酸的情況下,使通式[XIII]所示化合物與通式[XIV]所示化合物反應,而製造出通式[XV]所示化合物。
相對於化合物[XIII]1莫耳,於本反應中所使用的化合物[XIV]的使用量通常可由1~5莫耳範圍內適當選擇,較佳為1~2莫耳。
於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;如甲氧基鈉、乙氧基鈉、叔丁醇鉀等之醇的金屬鹽類;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[XIII]1莫耳,鹼的使用量可由0~5莫耳範圍內適當選擇,較佳為0~2莫耳。
於本反應中使用酸時,作為可使用的酸,可列舉例如:如鹽酸、氫溴酸、硫酸、硝酸、磷酸等之無機酸類;如乙酸或是三氟乙酸等之羧酸類。此外,相對於化合物[XIII]1莫耳,酸的使用量可由0~5莫耳範圍內適當選擇,較佳為0~2莫耳。
作為可於本反應中使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[XIII]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
本反應的反應溫度可由0℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於20℃~100℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~24小時。
反應結束後,可藉由進行將反應混合物注入水中,並濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[XV]。分離出的化合物[XV]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法6>
本發明化合物當中,通式[XVII]所示化合物可根據例如以下方法來製造。
(式中,m’係表示0或1,n”係表示1或2,m’及n”的和為1或2,R2
, A3
, A4
, A5
, A6
, A7
, A8
, A9
及R1 0
係表示與上述相同的意義)
即,可透過在適當的溶劑中且存在或是不存在催化劑的情況下,使通式[XVI]所示化合物與適當的氧化劑反應,而製造出通式[XVII]所示化合物。
作為可於本反應中使用的溶劑,可列舉例如:如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;水或是此等的混合溶劑。此外,相對於化合物[XVI]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
作為於本反應中可使用的氧化劑,可列舉例如:如間氯過苯甲酸、過氧甲酸、過氧乙酸或是三氟過氧乙酸等之有機過氧化物;如過氧化氫、過錳酸鉀、OxoneTM
(E.I.杜邦公司商品名稱:過硫酸氫鉀含有物)等之無機過氧化物;如過碘酸鈉或是次氯酸鈉等之氫鹵酸鹽類等。此外,相對於化合物[XVI]1莫耳,氧化劑的使用量可由0.5~5莫耳範圍內適當選擇,較佳為0.9~3莫耳。
作為可於本反應中使用的催化劑,可列舉例如五氧化二釩、偏釩酸鈉、鎢酸鈉等。此外,相對於化合物[XVI]1莫耳,催化劑的使用量可由0.001~10莫耳之範圍中適當選擇,較佳為0.01~1莫耳。
本反應的反應溫度可由-78℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於-10℃~100℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~24小時。
反應結束後,可藉由在將反應混合物注入水中或是濃縮等操作之後,進行濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[XVII]。分離出的化合物[XVII]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法7>
本發明化合物當中,通式[XX]所示化合物可根據例如以下方法來製造。
(式中,n’係表示0或1,R1
, R2
, A3
, A4
, A5
, A6
, A7
, A8
, A9
及R1 0
係表示與上述相同的意義)。
即,可透過在適當的溶劑中且存在或是不存在適當的鹼的情況下,使化合物[XIX]或其鹽與化合物[XVIII]及適當的氧化劑反應,而製造出通式[XX]所示化合物。
相對於化合物[XVIII]1莫耳,於本反應中所使用的化合物[XIX]的使用量通常可由1~10莫耳範圍內適當選擇,較佳為1~5莫耳。
作為本反應中可使用的氧化劑,可列舉:如氯、溴、碘、氯胺、N-氯丁二醯亞胺(NCS)、N-溴丁二醯亞胺(NBS)、N-碘半胱氨酸(NIS)、1,3-二氯-5,5-二甲基乙內醯脲(DCH)、1,3-二溴-5,5-二甲基乙丹(DBH)、1-溴-3-氯-5,5-二甲基乙丹(BCDMH)等之鹵化劑;如(二氯碘)苯、(二乙醯氧基碘)苯、(雙(三氟乙醯氧基)碘)苯、碘基苯、碘氧基苯、2-碘氧基苯甲酸(IBX)、戴斯-馬丁氧化劑(Dess-Martin peryodinan)(DMP)、2-碘代苯磺酸(IBS)等之超價碘原子化合物等。此外,相對於化合物[XVIII]1莫耳,氧化劑的使用量可由0.5~5莫耳之範圍內適當選擇,較佳為0.9~3莫耳。
於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀、氧化鎂、氧化鋁等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;如甲氧基鈉、乙氧基鈉、叔丁醇鉀等之醇的金屬鹽類;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[XVIII]1莫耳,鹼的使用量可由0~20莫耳範圍內適當選擇,較佳為0~10莫耳。
作為可於本反應中使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;或是此等的混合溶劑。此外,相對於化合物[XIII]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
本反應係可視所需而在催化劑的存在之下進行。作為於本反應中所使用的催化劑,可列舉例如:乙酸銠(II)、三氟乙酸銠(II)、三苯乙酸銠(II)、新戊酸銠(II)、辛酸銠(II)、雙[銠(α, α, α’, α’-四甲基-1,3-苯二丙酸]、乙醯氨基銠(II)等。此外,相對於化合物[XVIII]1莫耳,催化劑的使用量可由0.001~10莫耳之範圍內適當選擇,較佳為0.005~1莫耳。
本反應的反應溫度可由-78℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於0℃~100℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~48小時。
反應結束後,可藉由進行將反應混合物注入水中,並濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[XX]。分離出的化合物[XX]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法8>
本發明化合物當中,通式[XXII]所示化合物可根據例如以下方法來製造。
(式中,R1
, R2
, A3
, A4
, A5
, A6
, A7
, A8
, A9
及R1 0
係表示與上述相同的意義)
即,可透過在適當的溶劑中且存在或是不存在適當的鹼的情況下,使化合物[XIX]或其鹽與化合物[XXI]及適當的氧化劑反應,而製造出通式[XXII]所示化合物。
相對於化合物[XXI]1莫耳,於本反應中所使用的化合物[XIX]的使用量通常可由1~100莫耳範圍內適當選擇,較佳為1~5莫耳。
作為可於本反應中使用的氧化劑,可列舉例如:如氯、溴、碘、氯胺、N-氯丁二醯亞胺(NCS)、N-溴丁二醯亞胺(NBS)、N-碘半胱氨酸(NIS)、1,3-二氯-5,5-二甲基乙內醯脲(DCH)、1,3-二溴-5,5-二甲基乙丹(DBH)、1-溴-3-氯-5,5-二甲基乙丹(BCDMH)等之鹵化劑;如(二氯碘)苯、(二乙醯氧基碘)苯、(雙(三氟乙醯氧基)碘)苯、碘基苯、碘氧基苯、2-碘氧基苯甲酸(IBX)、戴斯-馬丁氧化劑(Dess-Martin peryodinan)(DMP)、2-碘代苯磺酸(IBS)等之超價碘原子化合物等。此外,相對於化合物[XXI]1莫耳,氧化劑的使用量可由0.5~5莫耳之範圍內適當選擇,較佳為0.9~3莫耳。
於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀、氧化鎂、氧化鋁等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;如甲氧基鈉、乙氧基鈉、叔丁醇鉀等之醇的金屬鹽類;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[XXI]1莫耳,鹼的使用量可由0~20莫耳範圍內適當選擇,較佳為0~10莫耳。
作為可於本反應中使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;或是此等的混合溶劑。此外,相對於化合物[XXI]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
本反應係可視所需而在催化劑的存在之下進行。作為於本反應中所使用的催化劑,可列舉例如:乙酸銠(II)、三氟乙酸銠(II)、三苯乙酸銠(II)、新戊酸銠(II)、辛酸銠(II)、雙[銠(α, α, α’, α’-四甲基-1,3-苯二丙酸]、乙醯氨基銠(II)等。此外,相對於化合物[XXI]1莫耳,催化劑的使用量可由0.001~10莫耳之範圍內適當選擇,較佳為0.01~5莫耳。
本反應的反應溫度可由-78℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於0℃~100℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~48小時。
反應結束後,可藉由進行將反應混合物注入水中,並濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[XXII]。分離出的化合物[XXII]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法9>
本發明化合物當中,通式[XXVI]所示化合物可根據例如以下方法來製造。
(式中,R1 3
係表示C1
~C6
烷基;X, m, n, R1
, R2
, A3
, A4
, A5
, A6
及R9
係表示與上述相同的意義。)
即,透過化合物[XXIII]與化合物[XXIV]的雅普-克林格曼反應(Japp-Klingemann reaction)而獲得化合物[XXV]之後,再透過使其進行環化反應而獲得通式[XXVI]所示化合物。此外,通式[XXVI]所示化合物係可根據國際公開第2012/028332號、國際公開第2014/114649號說明書中所記載之方法或是適用其方法而製造。
化合物[XXVI]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法10>
本發明化合物當中,通式[XXIX]所示化合物可根據例如以下方法來製造。
(式中,X, m, n, R1
, R2
, A3
, A4
, A5
, A6
及R9
係表示與上述相同的意義)
即,透過化合物[XXIII]與化合物[XXVII]的雅普-克林格曼反應(Japp-Klingemann reaction)而獲得化合物[XXVIII]之後,再透過使其進行環化反應而獲得通式[XXIX]所示化合物。此外,通式[XXIX]所示化合物係可根據有機製備及程序國際(Organic Preparations and Procedures International), 2002年,
第34冊, 1號, 98-102頁中所記載之方法或是適用其方法而製造。
化合物[XXIX]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法11>
本發明化合物當中,通式[XXXIII]所示化合物可根據例如以下方法來製造。
(式中,Y係表示X或OR1 3
;X, m, n, R1
, R2
, A3
, A4
, A5
, A6
, R7
, R8
及R1 3
係表示與上述相同的意義。)
即,可透過在適當的溶劑中且存在或是不存在適當的鹼的情況下,使通式[XIII]所示化合物與化合物[XXX]或化合物[XXXI]反應而獲得化合物[XXXII]之後,再透過適當的氧化劑使其芳族化而製造出通式[XXXIII]所示化合物。
相對於化合物[XIII]1莫耳,於本反應中所使用的化合物[XXX]或[XXXI]的使用量通常可由1~10莫耳範圍內適當選擇,較佳為1~5莫耳。
於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;如甲氧基鈉、乙氧基鈉、叔丁醇鉀等之醇的金屬鹽類;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[XIII]1莫耳,鹼的使用量可由0~20莫耳範圍內適當選擇,較佳為0~10莫耳。
作為於本反應中可使用的氧化劑,可列舉例如:如2,3-二氯-5,6-二氰基對苯醌(DDQ)等之有機化合物;如過錳酸鉀、二氧化錳等之無機氧化物。此外,相對於化合物[XXXII]1莫耳,氧化劑的使用量可由0.1~5莫耳範圍內適當選擇,較佳為0.5~2莫耳。
作為可於本反應中使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[XIII]或化合物[XXXII]1莫耳,溶劑的使用量係為0.1~1000升,較佳為0.2~100升。
本反應的反應溫度可由-20℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於0℃~100℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~24小時。
反應結束後,可藉由進行將反應混合物注入水中,並濾取所析出的固體或是以有機溶劑萃取後濃縮等之操作,來分離化合物[XXXIII]。分離出的化合物[XXXIII]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法12>
本發明化合物當中,通式[XXXVI]所示化合物可根據例如以下方法來製造。
(式中, m, n, R1
, R2
, A3
, A4
, A5
, A6
, R9
及R1 0
係表示與上述相同的意義。)
即,可在透過通式[XXIII]所示化合物的重氮轉移(diazo transfer)反應而獲得化合物[XXXIV]之後,再透過與化合物[XXXV]的惠斯根(Huisgen)1,3-偶極環加成反應,而獲得通式[XXXVI]所示化合物。此外,通式[XXXIV]所示化合物係可根據有機通訊誌(Organic Letters),2007年, 第9冊, 9號, 1809-1811頁中所記載之方法或是適用其方法而製造。
化合物[XXXVI]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
<製造方法13>
本發明化合物當中,通式[XXXIX]所示化合物可根據例如以下方法來製造。
。
(式中,X, m, n, R1
, R2
, A3
, A4
, A5
, A6
, R7
及R1 3
係表示與上述相同的意義。)
即,(步驟13-1)可透過存在或是不存在適當的溶劑、且存在或是不存在適當的酸的情況下,使通式[XIII]所示化合物與氰酸鹽類反應,而製造出化合物[XXXVII]。此外,(步驟13-2)可透過存在或是不存在適當的溶劑,存在或是不存在適當的鹼的情況下,使通式[XI]所示化合物與胺基脲或是其鹽進行反應而製造化合物[XXXVII]。進一步地,(步驟13-3)可透過存在或是不存在適當的溶劑、且存在或是不存在適當的鹼或是適當的酸的情況下,使通式[XXXVII]所示化合物與通式[XXXVIII]所示化合物反應,而製造通式[XXXIX]所示化合物。
(步驟13-1)
作為可於本反應中所使用的氰酸鹽類,可列舉例如氰酸鋰、氰酸鈉、氰酸鉀、氰酸銨等。此外,相對於化合物[XIII]1莫耳,氰酸鹽類的使用量通常可由1~10莫耳之範圍內選擇,較佳為1~5莫耳。
當於本反應中使用酸時,作為可使用的酸,可列舉例如:如鹽酸、氫溴酸、硫酸、硝酸、磷酸等之無機酸類;如乙酸或是三氟乙酸等羰酸類;如甲磺酸、三氟甲磺酸、苯磺酸、甲苯磺酸等之磺酸類等。此外,相對於化合物[XIII]1莫耳,酸的使用量可由0~100莫耳之範圍內適當選擇,較佳為0~10莫耳。
當於本反應中使用溶劑時,作為可使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[XIII]1莫耳,溶劑的使用量係為0~1000升,較佳為0~100升。
本反應的反應溫度可由0℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於20℃~180℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~24小時。
反應結束後,可透過視所需濾出不溶物後,並且進行將反應混合物注入水中或進行濃縮等操作之後,再透過濾取所析出的固體或是以有機溶劑萃取後進行濃縮等之操作,來分離化合物[XXXVII]。分離出的化合物[XXXVII]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。此外,亦可在並未從反應混合物中分離出化合物[XXXVII]的情況下將其使用於步驟13-3。
(步驟13-2)
相對於化合物[XI]1莫耳,於本反應中所使用的胺基脲或是其鹽的使用量通常可由1~10莫耳之範圍內適當選擇,較佳為1~5莫耳。
當於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;如甲氧基鈉、乙氧基鈉、叔丁醇鉀等之醇的金屬鹽類;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[XI]1莫耳,鹼的使用量可由0~20莫耳範圍內適當選擇,較佳為0~10莫耳。
當於本反應中使用溶劑時,作為可使用的溶劑,可列舉例如:二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[XI]1莫耳,溶劑的使用量係為0~1000升,較佳為0~100升。
本反應的反應溫度可由0℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於20℃~180℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~24小時。
反應結束後,可透過視所需濾出不溶物後,並且進行將反應混合物注入水中或進行濃縮等操作之後,再透過濾取所析出的固體或是以有機溶劑萃取後進行濃縮等之操作,來分離化合物[XXXVII]。分離出的化合物[XXXVII]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。此外,亦可在並未從反應混合物中分離出化合物[XXXVII]的情況下將其使用於步驟13-3。
(步驟13-3)
相對於化合物[XXXVII]1莫耳,於本反應中所使用的化合物[XXXVIII]的使用量通常可由1~200莫耳之範圍內適當選擇,較佳為1~100莫耳。
當於本反應中使用鹼時,作為可使用的鹼,可列舉例如:如氫氧化鋰、氫氧化鈉、氫氧化鉀等之鹼金屬的氫氧化物;如氫氧化鈣、氫氧化鎂等之鹼土金屬的氫氧化物;如碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫等之鹼金屬的碳酸鹽;如碳酸氫鈉、碳酸氫鉀等之鹼金屬的碳酸氫鹽類;如氟化鈉、氟化鉀等之鹼金屬的氟化物或是磷酸三鉀等之無機鹼類;如氫化鋰、氫化鈉、氫化鉀等之金屬氫化物;如甲氧基鈉、乙氧基鈉、叔丁醇鉀等之醇的金屬鹽類;或是三乙胺、三丁胺、二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基氨基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯等之有機鹼類等。此外,相對於化合物[XXXVII]1莫耳,鹼的使用量可由0~20莫耳範圍內適當選擇,較佳為0~10莫耳。
於本反應中使用酸時,作為可使用的酸,可列舉例如:如鹽酸、氫溴酸、硫酸、硝酸、磷酸等之無機酸類;如乙酸或是三氟乙酸等羰酸類;如甲磺酸、三氟甲磺酸、苯磺酸、甲苯磺酸等之磺酸類等。此外,相對於化合物[XXXVII]1莫耳,酸的使用量可由0~100莫耳之範圍內適當選擇,較佳為0~10莫耳。
當於本反應中使用溶劑時,作為可使用的溶劑,可列舉例如:如二乙醚、甲基叔丁基醚、環戊基甲基醚、四氫呋喃、1,4-二噁烷、乙二醇二甲醚等之醚類;如苯、甲苯、二甲苯、均三甲苯、氯苯等之芳烴類;如二氯甲烷、氯仿、1,2-二氯乙烷等之鹵代烴類;如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等之非質子極性溶劑類;如甲醇、乙醇、2-丙醇、叔丁醇、甲基溶纖劑等之醇類;如乙腈、丙腈等之腈類;如戊烷、己烷、環己烷、庚烷等之脂肪烴類;如吡啶、吡啶啉、二甲吡啶等之吡啶類;如三乙胺、三丁胺等之三級胺類;水或是此等的混合溶劑。此外,相對於化合物[XXXVII]1莫耳,溶劑的使用量係為0~1000升,較佳為0~100升。
本反應的反應溫度可由0℃至反應體系中的回流溫度間的任意溫度之範圍內選擇,較佳可於20℃~180℃範圍內進行。
本反應的反應時間係依反應溫度、反應基質、反應量等而有所不同,惟通常為10分鐘~24小時。
反應結束後,可透過視所需濾出不溶物後,並且進行將反應混合物注入水中或進行濃縮等操作之後,再透過濾取所析出的固體或是以有機溶劑萃取後進行濃縮等之操作,來分離化合物[XXXIX]。分離出的化合物[XXXIX]可依所需而藉由柱色譜法、再結晶、蒸餾等進一步純化。
本發明之通式[II]及通式[V]所示唑衍生物,係為在製造本發明之通式[I]所示唑衍生物或是其農業上可允許的鹽時,作為中間產物的有用的化合物。
本發明之農藥組合物係含有本發明中以通式[I]所示唑衍生物或是其農業上可允許的鹽,以作為有效成分。
本發明之農藥組合物係可視所需而含有通常用於農藥製劑的添加成分(載體)。
本發明之有害生物防治劑係含有本發明中以通式[I]所示唑衍生物或是其農業上可允許的鹽,以作為有效成分。本發明之有害生物防治劑具代表性的係為殺蟲劑、殺蟎劑及殺線蟲劑。
本發明之有害生物防治劑係可視所需而含有通常用於農藥製劑的添加成分(載體)。
作為所述添加成分,可列舉:如固體載體或是液體載體等之載體、表面活性劑、黏合劑或賦黏劑、增黏劑、著色劑、展開劑、展著劑、防凍劑、防結塊劑、崩解劑、防分解劑等,亦可視其他所需而使用防腐劑、植物片等作為添加成分。另外,此等添加成分係可使用一種,或者也可組合兩種以上來使用。
以下針對上述添加成分進行說明。
作為固體載體,可列舉例如:如葉蠟石黏土、高嶺土黏土、矽石黏土、滑石、矽藻土、沸石、膨潤土、酸性白土、活性白土、坡縷石黏土、蛭石、珠光體、浮石、白碳(合成矽酸、合成矽酸鹽等)、二氧化鈦等之礦物系載體;如木粉、玉米桿、堅果殼、果核、稻殼、木屑、麩、大豆粉、纖維素粉、澱粉、糊精、醣類等之植物性載體;如碳酸鈣、硫酸銨、硫酸鈉、氯化鉀等之無機鹽類載體;如聚乙烯、聚丙烯、聚氯乙烯、聚乙酸乙烯酯、乙烯-乙酸乙烯共聚物、脲醛樹脂等之高分子載體等。
作為液體載體,可列舉例如:如甲醇、乙醇、丙醇、2-丙醇、丁醇、環己醇、溶纖劑等之一元醇類;如乙二醇、二甘醇、丙二醇、己二醇、聚乙醇、聚丙二醇、甘油等之多元醇類;如丙烯系二醇醚等之多元醇衍生物類;如丙酮、甲基乙基酮、甲基異丁基酮、二異丁基酮、環己酮、異佛爾酮等之酮類;如二乙醚、1,4-二噁烷、二丙醚、四氫呋喃等之醚類;如正烷烴、環烷烴、異鏈烷烴、煤油、礦物油等之脂肪烴類;如甲苯、C9
~C1 0
烷基苯、二甲苯、溶劑石腦油(solvent naphtha)、烷基萘、高沸點芳烴等之芳烴類;如1,2-二氯乙烷、氯仿、四氯化碳等之鹵代烴類;如乙酸乙酯、鄰苯二甲酸二異丙酯、鄰苯二甲酸二丁酯、鄰苯二甲酸二辛酯、己二酸二甲酯等之酯類;如γ-丁內酯等之內酯類;如N,N-二甲基甲醯胺、N,N-二乙基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮等之醯胺類;如乙腈等之腈類;如二甲亞碸等之硫化合物類;如大豆油、菜籽油、棉籽油、棕櫚油、蓖麻油等之植物油;以及水等。
作為表面活性劑並無特別限制,較佳為於水中凝膠化或是呈現膨潤性者,可列舉例如:山梨醇脂肪酸酯、聚氧乙烯山梨醇脂肪酸酯、蔗糖脂肪酸酯、聚氧乙烯脂肪酸酯、聚氧乙烯樹脂酸酯、聚氧乙烯脂肪酸二酯、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯二烷基苯基醚、聚氧乙烯烷基苯基醚福馬林縮合物、聚氧乙烯聚氧丙烯嵌段聚合物、烷基聚氧乙烯聚丙烯嵌段聚合物醚、聚氧乙烯烷基胺、聚氧乙烯脂肪酸醯胺、聚氧乙烯脂肪酸雙苯基醚、聚亞烷基芐基苯基醚、聚氧化烯苯乙烯基苯基醚、乙炔二醇、聚氧化烯加成的乙炔二醇、聚氧乙烯醚型聚矽氧、酯型聚矽氧、氟系表面活性劑、聚氧乙烯蓖麻油、聚氧乙烯固化蓖麻油等之非離子表面活性劑;如烷基硫酸鹽、聚氧乙烯烷基醚硫酸鹽、聚氧乙烯烷基苯基醚硫酸鹽、聚氧乙烯苯乙烯基苯基醚硫酸鹽、烷基苯磺酸鹽、木質素磺酸鹽、烷基磺基琥珀酸鹽、萘磺酸鹽、烷基萘磺酸鹽、萘磺酸之福馬林縮合物的鹽、烷基萘磺酸之福馬林縮合物的鹽、脂肪酸鹽、聚羧酸鹽、N-甲基脂肪酸肌氨酸鹽、樹脂酸鹽、聚氧乙烯烷基磷酸醚、聚氧乙烯烷基苯基醚磷酸酯等之陰離子性表面活性劑;如月桂胺鹽酸鹽、硬脂胺鹽酸鹽、油胺鹽酸鹽、硬脂胺乙酸鹽、硬脂基氨基丙胺乙酸鹽以及如烷基三甲基氯化銨、烷基二甲基氯化芐等之烷基胺鹽等的陽離子表面活性劑;如二烷基二氨基乙基甜菜鹼、烷基二甲基芐基甜菜鹼的甜菜鹼型、以及二烷基氨基乙基甘氨酸、烷基二甲基芐基甘氨酸等氨基酸型的兩性表面活性劑等。
作為黏合劑或是賦黏劑,可列舉例如:羧甲基纖維素或其鹽、糊精、水溶性澱粉、黃原膠、瓜爾豆膠、蔗糖、聚乙烯吡咯烷酮、阿拉伯膠(gum arabic)、聚乙烯醇、聚乙酸乙烯酯、聚丙烯酸鈉、平均分子量6000~20000的聚乙二醇、平均分子量10萬~500萬的聚環氧乙烷、天然磷脂(例如腦磷脂酸、卵磷脂等)等。
作為增黏劑,可列舉例如:如黃原膠、瓜爾豆膠、羧甲基纖維素、聚乙烯吡咯烷酮、羧乙烯基聚合物、丙烯酸類聚合物、澱粉衍生物、多醣類之水溶性高分子;如高純度膨潤土、白碳之無機細粉。
作為著色劑,可列舉例如:如氧化鐵、氧化鈦、紺青之無機顏料;如茜素染料、偶氮染料、金屬酞青染料之有機染料等。
作為展開劑,可列舉例如:聚矽氧系表面活性劑、纖維素粉、糊精、加工澱粉、聚氨基羧酸螯合物、交聯聚乙烯吡咯烷酮、馬來酸及苯乙烯類、甲基丙烯酸共聚物、多元醇之聚合物與二羧酸酐的半酯、聚苯乙烯磺酸的水溶性鹽等。
作為展著劑,可列舉例如:如磺基琥珀酸二烷基酯鈉、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯脂肪酸酯等各種表面活性劑;如石蠟、萜烯(terpene)、聚醯胺樹脂、聚丙烯酸酯、聚氧乙烯、蠟、聚乙烯基烷基醚、烷基酚福馬林縮合物、合成樹脂乳液等。
作為防凍劑,可列舉例如:乙二醇、二甘醇、丙二醇、甘油等之多元醇類等。
作為防結塊劑,可列舉例如:如澱粉、海藻酸、甘露糖、半乳糖等多醣類;聚乙烯吡咯烷酮、白碳、酯膠、石油樹脂等。
作為崩解劑,可列舉例如:三聚磷酸鈉蘇打、六偏磷酸蘇打、硬脂酸金屬鹽、纖維素粉、糊精、甲基丙烯酸酯之共聚物、聚乙烯吡咯烷酮、聚氨基羧酸螯合物、磺化苯乙烯/異丁烯/馬來酸酐共聚物、澱粉/聚丙烯腈接枝共聚物等。
作為防分解劑,可列舉例如:如沸石、生石灰、氧化鎂之乾燥劑;如酚系、胺系、硫系、磷酸系等之抗氧化劑;如水楊酸系、二苯甲酮系等之紫外線吸收劑等。
另一方面,於本發明之有害生物防治劑當中,當其中含有上述添加成分時,關於其含量比例,以質量基準計,固體載體或是液體載體等載體通常係選自5~95%,較佳為20~90%範圍;表面活性劑通常係選自0.1%~30%,較佳為0.5~10%範圍;其他添加劑係選自0.1%~30%,較佳為0.5~10%範圍。
本發明之有害生物防治劑係可製劑成:粉劑、粉粒劑、顆粒劑、可濕性粉劑、水溶劑、顆粒可濕性粉劑、錠劑、袋劑、乳劑、油劑、液劑、流動劑、乳化劑、微乳化劑、濃懸乳劑(suspo emulsion agent)、微噴霧劑、微膠囊劑、煙霧劑、氣霧劑、誘餌劑、糊劑等任意的劑型。
在實際使用此等製劑時,可依原樣使用,或者用諸如水的稀釋劑等來稀釋至預定濃度下使用。含有本發明之化合物的各種製劑或是其稀釋物的施用,通常係透過一般常用的施用方法來進行,即:噴灑(例如:噴霧、水霧化、粉霧化、灑粉、撒顆粒、施加於水面、箱式施塗等);施加於土壤(例如:混入、灌注等);施加於表面(例如塗佈、塗粉、覆蓋等);種子處理(例如塗抹、塗粉處理)、浸漬、毒餌、施加煙霧等。此外,也可將所述有效成分混合進飼料並提供給家畜,可防治其排泄物中產生、生長害蟲,特別是有害的昆蟲。
本發明之有害生物的防治方法係可藉由以上述施用方法來使用本發明之通式[I]所示3-(1H-1,2,4-三唑-1-基)苯甲醯胺衍生物或是其農業上可允許的鹽的有效成分量來進行。
關於本發明之有害生物防治劑中的有效成分的摻入比例(質量%),係可視所需而適當選擇。例如,當為粉劑、粉粒劑、微粒劑時係可適當選自0.01~20%,又以0.05~10%範圍為較佳;當為顆粒劑時係可適當選自0.1~30%,又以0.5~20%範圍為較佳;當為可濕性粉劑、顆粒可濕性粉劑時係可適當選自1~70%,又以5~50%範圍為較佳;當為水溶劑、液劑等時係可適當選自1~95%,又以10~80%範圍為較佳;當為乳劑等時係可適當選自5~90%,又以10~80%範圍為較佳;當為油劑等時係可適當選自1~50%,又以5~30%範圍為較佳;當為流動劑等時係可適當選自5~60%,又以10~50%範圍為較佳;當為乳化劑、微乳化劑、濃懸乳劑等時係可適當選自5~70%,又以10~60%範圍為較佳;當為錠劑、誘餌劑、糊劑時係可適當選自1~80%,又以5~50%範圍為較佳;當為煙霧劑等時係可適當選自0.1~50%,又以1~30%範圍為較佳;當為氣霧劑等時係可適當選自0.05~20%,又以0.1~10%範圍為較佳。
將此等製劑稀釋至適當濃度,並且噴灑或是直接施用。
關於施用本發明之有害生物防治劑,當以稀釋劑稀釋下使用時,通常在0.1~5000ppm的有效成分濃度下進行。當直接使用製劑時,作為有效成分化合物之每單位面積的施用量可在每公頃0.1~5000g之間使用,惟並不限於此。
此外,不言而喻地,關於本發明之有害生物防治劑,即使是單獨地以本發明之化合物作為有效成分仍足夠有效,亦可依所需而與其他肥料、農藥混用、併用,例如:殺蟲劑、殺蟎劑、殺線蟲劑、增效劑、殺菌劑、抗病毒劑、引誘劑、除草劑、植物生長調節劑等,此時可能顯現出更優異的效果。
接著,示例可混合或是併用的公知的殺蟲劑、殺蟎劑、殺線蟲劑、增效劑化合物。
殺蟲活性成分:
氟丙菊酯(acrinathrin)、印楝素(azadirachtin)、甲基吡啶磷(azamethiphos)、阿西非那比(acynonapyr)、乙基穀硫磷(azinphos-ethyl)、甲基穀硫磷(azinphos-methyl)、乙醯喹啉(acequinocyl)、亞滅培(acetamiprid)、乙醯蟲腈(acetoprole)、乙醯甲胺磷(acephate)、三唑錫(azocyclotin)、阿維菌素(abamectin)、雙丙環蟲酯(afidopyropen)、阿福拉納(afoxolaner)、磺胺蟎酯(amidoflumet)、雙甲脒(amitraz)、棉鈴威(alanycarb)、涕滅威(aldicarb)、涕滅碸威(aldoxycarb)、丙烯除蟲菊(allethrin)[包括d~Cis-trans-構體、d-trans-構體]、氯唑磷(isazophos)、氯唑磷(isamidofos)、水胺硫磷(isocarbophos)、加福松(isoxathion)、異噁唑蟲醯胺(isocycloseram)、甲基異硫磷(isofenphos-methyl)、滅必蝨(isoprocarb)、ε-甲氧苄氟菊酯(epsilon-metofluthrin)、ε-甲氧苄氟菊酯(epsilon-momfluorothrin)、伊維菌素(ivermectin)、伊米卡福斯(imicyafos)、益達胺(imidacloprid)、炔咪菊酯(imiprothrin)、因得克(indoxacarb)、益化利(esfenvalerate)、殺蟲丹(ethiofencarb)、乙硫磷(ethion)、益斯普(ethiprole)、二溴化乙烯(ethylene dibromide)、依託唑(etoxazole)、依芬寧(etofenprox)、乙草胺(ethoprophos)、乙嘧硫磷(etrimfos)、阿瑪菌素(emamectin)、阿瑪菌素苯甲酸酯(emamectin benzoate)、安殺番(endosulfan)、烯炔菊酯(empenthrin)、歐佐索伏(oxazosulfyl)、毆殺(oxamyl)、滅多松(oxydemeton-methyl)、異亞碸磷(oxydeprofos)、氧化樂果(omethoate)、硫線磷(cadusafos)、κ-七氟菊酯(kappa-tefluthrin)、k-聯苯菊酯(kappa-bifenthrin)、水黃皮次素(karanjin)、培丹(cartap)、加保利(carbaryl)、丁基加保扶(carbosulfan)、加保扶(carbofuran)、林丹(gamma-bhc)、滅爾蝨(xylylcarb)、喹惡磷(quinalphos)、烯蟲炔酯(kinoprene)、蟎離丹(chinomethionat)、蠅毒磷(coumaphos)、冰晶石(cryolite)、可丁尼(clothianidin)、四蟎嗪(clofentezine)、環蟲醯肼(chromafenozide)、氯蟲醯胺(chlorantraniliprole)、氯氧磷(chlorethoxyfos)、氯丹(chlordane)、硝基氯仿(chloropicrin)、氯吡硫磷(chlorpyrifos)、甲基氯蜱硫磷(chlorpyrifos-methyl)、溴蟲腈(chlorfenapyr)、氯芬松(chlorfenvinphos)、氟啶脲(chlorfluazuron)、氯甲硫磷(chlormephos)、右旋反式氯丙炔菊酯(chloroprallethrin)、氰蟲醯胺(cyazypyr)、氰乃松(cyanophos)、丁醚脲(diafenthiuron)、除線特(diamidafos)、溴氰蟲醯胺(cyantraniliprole)、腈吡蟎酯(cyetpyrafen)、得氯蹣(dienochlor)、腈吡蟎酯(cyenopyrafen)、蔬果磷(dioxabenzofos)、苯蟲醚(diofenolan)、環溴蟲醯胺(cyclaniliprole)、環氧蟲啶(cycloxaprid)、百治磷(dicrotophos)、除線磷(dichlofenthion)、環丁氟崙(cyclobutrifluram)、乙氰菊酯(cycloprothrin)、二氯松(dichlorvos)、二氯噻吡嘧啶(dicloromezotiaz)、大克蟎(dicofol)、地昔尼爾(dicyclanil)、乙拌磷(disulfoton)、呋蟲胺(dinotefuran)、敵蟎能(dinobuton)、氯氟氰蟲醯胺(cyhalodiamide)、賽洛寧(cyhalothrin)[包括gamma-構體,lambda-構體]、賽酚寧(cyphenothrin)[包括(1r)-trans-構體]、賽扶寧(cyfluthrin)[包括beta-構體]、除蟲脲(diflubenzuron)、丁氟蟎酯(cyflumetofen)、氟蟎嗪(diflovidazin)、環丙氟蟲胺(cyproflanilide)、環己錫(cyhexatin)、賽滅寧(cypermethrin)[包括alpha-構體,beta-構體,theta-構體,zeta-構體]、迪普羅匹利達茲(dimpropyridaz)、二甲基-2,2,2-三氯-1-羥基乙基磷酸酯(dep)、甲基毒蟲畏(dimethylvinphos)、大滅松(dimethoate)、四氟甲醚菊酯(dimefluthrin)、矽護芬(silafluofen)、賽滅淨(cyromazine)、賜諾特(spinetoram)、賜諾殺(spinosad)、賜派芬(spirodiclofen)、賜派滅(spirotetramat)、甲氧呱啶乙酯(spiropidion)、賜滅芬(spiromesifen)、薩爾科福隆鈉鹽(sulcofuron-sodium)、氟蟲胺(sulfluramid)、速殺氟(sulfoxaflor)、治螟磷(sulfotep)、大利松(diazinon)、賽果培(thiacloprid)、賽速安(thiamethoxam)、3-苯基-5-(噻吩-2-基)-[1,2,4]噁二唑(tioxazafen)、硫敵克(thiodicarb)、殺蟲環(thiocyclam)、殺蟲雙(thiosultap)、硫磷嗪(thionazin)、硫伐隆(thiofanox)、硫滅松(thiometon)、克羅吡唑羅(tyclopyrazoflor)、四氯蟲醯胺(tetrachlorantraniliprole)、四氯烯磷(tetrachlorvinphos)、四氯二苯碸(tetradifon)、氟氰蟲醯胺(tetraniliprole)、四氟醚菊酯(tetramethylfluthrin)、治滅寧(tetramethrin)、丁基嘧啶磷(tebupirimfos)、得芬諾(tebufenozide)、得芬瑞(tebufenpyrad)、七氟菊酯(tefluthrin)、得福隆(teflubenzuron)、滅賜松(demeton-s-methyl)、亞培松(temephos)、第滅寧(deltamethrin)、託福松(terbufos)、泰滅寧(tralomethrin)、四氟苯菊酯(transfluthrin)、唑蚜威(triazamate)、三落松(triazophos)、三氯松(trichlorfon)、三福隆(triflumuron)、三氟苯嘧啶(triflumezopyrim)、三甲威(trimethacarb)、脫芬瑞(tolfenpyrad)、乃力松(naled)、尼古丁(nicotine)、尼古氟若(nicofluprole)、烯啶蟲胺(nitenpyram)、莫昔克丁(nemadectin)、諾伐隆(novaluron)、諾福隆(noviflumuron)、蠟蚧輪枝菌(verticillium lecanii)、烯蟲乙酯(hydroprene)、液化澱粉芽孢桿菌(bacillus amyloliquefaciens)、堅硬芽孢桿菌(bacillus firmus)、圓形芽孢桿菌(bacillus sphaericus)、枯草桿菌(bacillus subtillis)、蘇雲金芽孢桿菌(bacillus thuringiensis)、蘇雲金芽孢桿菌(bacillus thuringiensis)所生產的昆蟲毒素、蘇力菌鮎澤亞種(bacillus thuringiensis subsp. aizawai)、蘇力菌以色列亞種(bacillus thuringiensis subsp. israelensis)、蘇力菌庫斯克亞種(bacillus thuringiensis subsp. kurstaki)、蘇力菌擬步行蟲亞種(bacillus thuringiensis subsp. tenebrionis)、甲蟲芽孢桿菌(bacillus popilliae)、巴斯德芽孢菌(pasteuriapenetrans)、繁米松(vamidothion)、巴拉松(parathion)、甲基巴拉松(parathion-methyl)、合芬寧(halfenprox)、氯蟲醯肼(halofenozide)、二丙烯除蟲菊酯(bioallethrin)、生物烯丙菊酯-S-環戊烯基(bioallethrin s~Cyclopentenyl)、列滅寧(bioresmethrin)、雙-(2-氯-1-甲基乙基)酯(DCIP)、雙三氟蟲脲(bistrifluron)、愛美松(hydramethylnon)、必芬蟎(bifenazate)、畢芬寧(bifenthrin)、派氟米德(pyflubumide)、協力精(piperonyl butoxide)、派滅淨(pymetrozine)、白克松(pyraclofos)、啶吡唑蟲胺(pyrafluprole)、必芬松(pyridaphenthion)、畢達本(pyridaben)、三氟甲吡醚(pyridalyl)、吡氟喹咗(pyrifluquinazon)、比普魯(pyriprole)、利普芬(pyriproxyfen)、比加普(pirimicarb)、畢汰芬(pyrimidifen)、嘧蟎胺(pyriminostrobin)、亞特松(pirimiphos-methyl)、除蟲菊素(pyrethrine)、氨磺磷(famphur)、芬普尼(fipronil)、芬殺蟎(fenazaquin)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬諾克(fenoxycarb)、芬硫克(fenothiocarb)、苯醚菊酯(phenothrin)[包括(1r)-trans-構體]、丁基滅必蝨((fenobucarb)、芬殺松(fenthion)、賽達松(phenthoate)、芬化利(fenvalerate)、芬普蟎(fenpyroximate)、芬佈賜(fenbutatin oxide)、芬普寧(fenpropathrin)、大福松(fonofos)、硫醯氟(sulfuryl fluoride)、佈嘉信(butocarboxim)、丁酮碸威(butoxycarboxim)、布芬淨(buprofezin)、氟線威(furathiocarb)、普亞列寧(prallethrin)、嘧蟎酯(fluacrypyrim)、三氟咪啶醯胺(fluazaindolizine)、氟佐隆(fluazuron)、氟速芬(fluensulfone)、氟派瑞(fluopyram)、氟乙酸鈉鹽(sodium fluoroacetate)、氟噁唑醯胺(fluxametamide)、氟蟎脲(flucycloxuron)、護賽寧(flucythrinate)、氟硫滅(flusulfamide)、賽扶寧(fluthrin)、福化利(fluvalinate) [包括tau-構體]、氟吡呋喃酮(flupyradifurone)、吡氟硫磷(flupyrazofos)、氟匹明(flupyrimin)、丁烯氟蟲腈(flufiprole)、嘧蟲胺(flufenerim)、氟菌蟎酯(flufenoxystrobin)、氟芬隆(flufenoxuron)、氟赫吩(fluhexafon)、氟大滅(flubendiamide)、氟朋芬克(flupentiofenox)、氟美林(flumethrin)、弗雷拉納(fluralaner)、氟蟲芬(flurimfen)、茉莉酮(jasmone)、順式茉莉酮(cis-jasmone)、普硫松(prothiofos)、氟蟲清(protrifenbute)、氟尼胺(flonicamid)、加護松(propaphos)、毆蟎多(propargite)、佈飛松(profenofos)、布洛立德(broflanilide)、丙氟菊酯(profluthrin)、撲達松(propetamphos)、安丹(propoxur)、氟麥托醌(flometoquin)、新殺蟎(bromopropylate)、合賽多(hexythiazox)、六伏隆(hexaflumuron)、細腳擬青黴(pacilimyces tenuipes)、玫煙色擬青黴菌(paecilomyces fumosoroceus)、淡紫擬青黴(paecilomyces lilacinus)、右旋七氟甲醚菊酯(heptafluthrin)、飛達松(heptenophos)、百滅寧(permethrin)、異噻蟲唑(benclothiaz)、百利莫桑(benzpyrimoxan)、免速達(bensultap)、西脫蟎(benzoximate)、免敵克(bendiocarb)、免扶克(benfuracarb)、卵孢白殭菌((beauveria tenella)、巴氏蠶白僵菌(beauveria bassiana)、布氏白僵菌(beauveria brongniartii)、巴賽松(phoxim)、裕必松(phosalone)、福賽絕(fosthiazate)、吉福松(fosthietan)、福賜米松(phosphamidon)、益滅松(phosmet)、瀏陽黴素複合物(polynactins)、覆滅蟎(formetanate)、福瑞松(phorate)、機油(machine oil)、馬拉硫磷(malathion)、密滅汀(milbemectin)、滅加松(mecarbam)、甲亞碸磷(mesulfenfos)、納乃得(methomyl)、聚乙醛(metaldehyde)、美氟綜(metaflumizone)、達馬松(methamidophos)、梅瑟姆(metham)、滅賜克(methiocarb)、滅大松(methidathion)、異硫氰酸甲酯(methyl isothiocyanate)、溴化甲烷(methyl bromide)、甲氧氯(methoxychlor)、滅芬諾(methoxyfenozide)、甲菊酯(methothrin)、甲氟菊酯(metofluthrin)、美賜平(methoprene)、治滅蝨(metolcarb)、速滅磷(mevinphos)、美氟菊酯(meperfluthrin)、植物單孢菌(monacrosporium phymatophagum)、亞素靈(monocrotophos)、氟氟辛(momfluorothrin)、哈茨木黴(trichoderma harzianum)、合成費洛蒙a(litlure-a)、合成費洛蒙b(litlure-b)、磷化鋁(aluminium phosphide)、磷化鋅(zinc phosphide)、膦(phosphine)、祿芬隆(lufenuron)、瑞斯卡羅(rescalure)、雷斯美林(resmethrin)、雷皮菌素(lepimectin)、魚藤精(rotenone)、核多角體病毒封埋體、芬佈賜(fenbutatin oxide)、氰化鈣(calcium cyanide)、有機錫化合物(organotins)、硫酸化菸鹼(nicotine-sulfate)、(z)-11-十四碳烯基=醋酸鹽、(z)-11-十六烯、(z)-11-十六碳烯基=醋酸鹽、(z)-9,12-十四碳二烯基=醋酸鹽、(z)-9-十四烯-1-醇、(z,e)-9,11-十四碳二烯基=醋酸鹽、(z,e)-9,12-十四碳二烯基=醋酸鹽、1,1,1-三氯-2,2-雙(4-氯苯基)乙烷(DDT)、1,3‐二氯丙烯(1,3-dichloropropene)、2,4-二氯-5-{2-[4-(三氟甲基)苯基]乙氧基}苯基 2,2,2-三氟乙基亞碸(化學名稱、CAS登錄編號:1472052-11-1)、2,4-二甲基-5-[6-(三氟甲硫基)己氧基]苯基-2,2,2-三氟乙基亞碸(化學名稱、CAS登錄編號:1472050-34-2)、2-{2-氟-4‐甲基-5-[(2,2,2-三氟乙基)磺胺]苯氧基}-5-(三氟甲基)吡啶(化學名稱、CAS登錄編號:1448758-62-0)、3-氯-2-{2-氟-4‐甲基-5-[(2,2,2-三氟乙基)磺胺]苯氧基}-5-(三氟甲基)吡啶(化學名稱、CAS登錄編號:1448761-28-1)、4,6-二硝基-o-甲酚(DNOC)、4-氟-2-甲基-5-(5,5-二甲基己氧基]苯基2,2,2-三氟乙基亞碸(化學名稱、CAS登錄編號:1472047-71-4)、Bt蛋白質 (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, cry3Bb, Cry34/35Ab1)、CL900167(編號)、NA-85(編號)、ni-30(編號)、O,O-二乙基-O-[4-(二甲基氨磺醯基)苯基]-磷酸硫代磷酸酯(dsp)、O-乙基-O-4-(硝基苯基)苯基硫代磷酸酯 (EPN)、RU15525(編號)、XMC(XMC)、Z-13-二十碳烯-10-酮、ZXI8901(編號)、F4260(編號)。
接著,示例可混合或組合使用的已知殺菌劑或病害防治化合物。
殺菌活性成分:
氮雜康唑(azaconazole)、苯並氨基苯甲酸-S-甲基(acibenzolar-s-methyl)、氮雜氧嘧啶(azoxystrobin)、安那嗪(anilazine)、阿米磺溴(amisulbrom)、氨基吡啶(aminopyrifen)、阿米曲汀(ametoctradin)、二甲基嗎啉(aldimorph)、亞汰尼(isotianil)、亞派占(isopyrazam)、異丙噻菌胺(isofetamid)、異氟西蘭(isoflucypram)、亞賜圃(isoprothiolane)、種菌唑(ipconazole)、氟醚菌醯胺(ipflufenoquin)、依芬氟康唑(ipfentrifluconazole)、異丙洛酮(iprodione)、異丙洛威(iprovalicarb)、異丙洛芬(iprobenfos)、依滅列(imazalil)、烷苯磺酸鹽(iminoctadine-albesilate)、雙胍辛酸三乙酸鹽(iminoctadine- triacetate)、咪苯並咪唑(imibenconazole)、吡蟲醯胺(inpyrfluxam)、抑靈素A(imprimatin a)、抑靈素B(imprimatin b)、乙二磷(edifenphos)、依他康唑(etaconazole)、乙胺磷(ethaboxam)、乙菌定(ethirimol)、乙氧基喹(ethoxyquin)、乙二唑(etridiazole)、雌三丁酯(enestroburin)、恩諾斯特羅賓(enoxastrobin)、環氧康唑(epoxiconazole)、有機油(organic oils)、惡二噁基(oxadixyl)、惡嗪基吡咯(oxazinylazole)、氧雜呱啶(oxathiapiprolin)、氧羰基(oxycarboxin)、快得寧(oxine~Copper)、土黴素(oxytetracycline)、富馬酸惡咪唑(oxpoconazole-fumarate)、歐索林酸(oxolinic acid)、辛酸銅(copper dioctanoate)、辛噻酮(octhilinone)、甲酸酯(ofurace)、肟醚菌胺(orysastrobin)、鄰苯基苯酚(o-phenylphenol)、嘉賜黴素(kasugamycin)、敵菌丹(captafol)、加普胺(carpropamid)、貝芬替(carbendazim)、萎銹靈(carboxin)、香芹酮(carvone)、快諾芬(quinoxyfen)、喹諾福美林(quinofumelin)、蟎離丹(chinomethionat)、蓋普丹(captan)、喹康唑(quinconazole)、五氯硝基苯(quintozene)、雙胍鹽(guazatine)、硫雜靈(cufraneb)、甲香菌酯(coumethoxystrobin)、香豆素(coumoxystrobin)、甲基克收欣(kresoxim-methyl)、克羅康(clozylacon)、乙菌利(chlozolinate)、氯隱康嗪(chloroinconazide)、四氯異苯腈(chlorothalonil)、地茂丹(chloroneb)、氰唑胺(cyazofamid)、二氫大麻酚(diethofencarb)、雙氯氰菌胺(diclocymet)、抑菌靈(dichlofluanid)、雙環噻唑(dichlobentiazox)、達滅淨(diclomezine)、氯硝胺(dicloran)、雙氯酚(dichlorophen)、二噻農(dithianon)、達克利(diniconazole)、高效達可利(diniconazole-m)、鋅乃浦(zineb)、敵蟎普(dinocap)、敵滅創(dipymetitrone)、二苯胺(diphenylamine)、待克利(difenoconazole)、氟苯乙胺(cyflufenamid)、雙氟甲蝶呤(diflumetorim)、環丙唑(cyproconazole)、賽普洛(cyprodinil)、西美康唑(simeconazole)、甲蟲靈(dimethirimol)、二甲基二硫(dimethyl disulfide)、二甲嗎啡(dimethomorph)、環丙沙胺(cymoxanil)、二羥木糖苷(dimoxystrobin)、羅氏假單胞菌・hai-0804(pseudomonas rhodesiae hai-0804)、福美鋅(ziram)、矽硫菌素(silthiofam)、鏈黴素(streptomycin)、螺環菌胺(spiroxamine)、氟唑環菌胺(sedaxane)、唑醯胺(zoxamide)、苯並烯氟菌唑(solatenol)、邁隆(dazomet)、大孢青黴菌(talaromyces flavus)、噻菌胺(tiadinil)、噻菌靈(thiabendazole)、福美雙(thiram)、硫氰酸酯(thiophanate)、甲基硫菌靈(thiophanate-methyl)、噻氟菌胺(thifluzamide)、福美雙(thiram)、四氯硝基苯(tecnazene)、泰洛芬(tecloftalam)、四克利(tetraconazole)、十碳威(debacarb)、得克利(tebuconazole)、替布氟喹(tebufloquin)、特比奈芬(terbinafine)、多寧(dodine)、嗎菌靈(dodemorph)、三苯甲酚(triadimenol)、三泰芬(triadimefon)、三氮嗪(triazoxide)、三氯醯胺(trichlamide)、氯啶菌酯(triclopyricarb)、深綠木黴菌(trichoderma atroviride)、三賽唑(tricyclazole)、滅菌唑(triticonazole)、克啉菌(tridemorph)、賽福座(triflumizole)、三氟敏(trifloxystrobin)、嗪氨靈(triforine)、甲苯氟磺胺(tolylfluanid)、甲基立枯磷(tolclofos-methyl)、甲磺菌胺(tolnifanide)、三氟甲氧威(tolprocarb)、那班(nabam)、納他黴素(natamycin)、那夫梯芬(naftifine)、氯啶(nitrapyrin)、酞菌酯(nitrothal-isopropyl)、氟苯嘧啶醇(nuarimol)、亞納銅(copper nonyl phenol sulphonate)、枯草芽孢桿菌(bacillus subtilis)(strain:qst 713)、維利黴素(validamycin)、霜黴滅(valifenalate)、四唑吡氨酯(picarbutrazox)、聯苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、氟唑菌醯羥胺(pydiflumetofen)、比多農(bitertanol)、樂殺蟎(binapacryl)、日柏酚(hinokitiol)、聯苯(biphenyl)、粉病靈(piperalin)、殺紋寧(hymexazol)、唑菌酯(pyraoxystrobin)、百克敏(pyraclostrobin)、吡嗪醯胺(pyraziflumid)、吡菌磷(pyrazophos)、吡丙炔(pyrapropoyne)、嘧菌酯(pyrametostrobin)、吡利歐芬農(pyriofenone)、啶菌噁唑(pyrisoxazole)、吡利達庫(pyridachlometyl)、啶斑肟(pyrifenox)、稗草丹(pyributicarb)、吡菌苯威(pyribencarb)、派美尼(pyrimethanil)、咯喹酮(pyroquilon)、乙烯菌核利(vinclozolin)、富爾邦(ferbam)、惡唑菌酮(famoxadone)、葉枯淨(phenazine oxide)、咪唑菌酮(fenamidone)、烯肟菌胺(fenaminstrobin)、芬瑞莫(fenarimol)、芬諾尼(fenoxanil)、富米綜(ferimzone)、拌種咯(fenpiclonil)、芬呱沙米(fenpicoxamid)、芬吡拉明(fenpyrazamine)、芬克座(fenbuconazole)、甲呋醯胺(fenfuram)、苯鏽啶(fenpropidin)、芬普福(fenpropimorph)、環醯菌胺(fenhexamid)、福爾培(folpet)、熱必斯(phthalide)、布瑞莫(bupirimate)、麥穗寧(fuberidazole)、保米黴素(blasticidin-s)、福拉比(furametpyr)、呋霜靈(furalaxyl)、2-呋喃甲酸(furancarboxylic acid)、扶吉胺(fluazinam)、氟茚唑菌胺(fluindapyr)、氟嘧菌酯(fluoxastrobin)、氟噁吡普林(fluoxapiprolin)、氟比來(fluopicolide)、氟吡胺(fluopimomide)、氟派瑞(fluopyram)、氟醯亞胺(fluoroimide)、氟克殺(fluxapyroxad)、氟喹康唑(fluquinconazole)、氟康唑(furconazole)、順式氟康唑(furconazole-cis)、護汰寧(fludioxonil)、護矽得(flusilazole)、氟硫滅(flusulfamide)、氟噻唑菌腈(flutianil)、福多寧(flutolanil)、護汰芬(flutriafol)、氟菌蟎酯(flufenoxystrobin)、氟苯醚醯胺(flubeneteram)、弗美多佛(flumetover)、氟嗎啉(flumorph)、普快淨(proquinazid)、撲克拉(prochloraz)、撲滅寧(procymidone)、胺丙威(prothiocarb)、丙硫唑(prothioconazole)、溴硝醇(bronopol)、普拔克(propamocarb-hydrochloride)、普克利(propiconazole)、甲基鋅乃浦(propineb)、撲殺熱(probenazole)、溴克座(bromuconazole)、氟滅特喹(flometoquin)、氟吡草胺(florylpicoxamid)、菲克利(hexaconazole)、本達樂(benalaxyl)、右本達樂(benalaxyl-m)、麥鏽靈(benodanil)、免賴得(benomyl)、披扶座(pefurazoate)、平克座(penconazole)、賓克隆(pencycuron)、苯並烯氟菌唑(benzovindiflupyr)、苯並噻唑(benthiazole)、異丙基苯噻菌胺(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、氟唑菌苯胺(penflufen)、白克列(boscalid)、福賽得(fosetyl)(鋁、鈣、鈉)、多氧黴素(polyoxin)、聚碳酸酯(polycarbamate)、波爾多(bordeaux mixture)、代森錳銅(mancopper)、鋅錳乃浦(mancozeb)、曼普胺(mandipropamid)、曼德托賓(mandestrobin)、錳乃浦(maneb)、邁克尼(myclobutanil)、礦物油(mineral oils)、米多黴素(mildiomycin)、滅速克(methasulfocarb)、威百畝(metam)、滅達樂(metalaxyl)、右滅達樂(metalaxyl-m)、免得爛(metiram)、滅塔比羅(metyltetraprole)、滅特座(metconazole)、苯氧菌胺(metominostrobin)、苯菌酮(metrafenone)、滅派林(mepanipyrim)、氯氟醚菌唑(mefentrifluconazole)、消蟎多(meptyldinocap)、滅普寧(mepronil)、丁基氨基甲酸碘代丙炔酯(iodocarb)、昆布多醣(laminarin)、根瘤菌(rhizobium vitis)、亞磷酸及鹽(phosphorous acid and salts)、鹼性氯氧化銅(copper oxychloride)、銀(silver)、酸化第一銅(cuprous oxide)、水酸化第二銅(copper hydroxide)、碳酸氫鉀(potassium bicarbonate)、碳酸氫鈉(sodium bicarbonate)、硫(sulfur)、硫酸氧喹啉(oxyquinoline sulfate)、硫酸銅(copper sulfate)、(3,4-二氯異噻唑-5-基)甲基4-(叔丁基)苯甲酸酯(化學名稱、CAS登錄編號:1231214-23-5)、BAF-045(編號)、BAG-010(編號)、UK-2A(編號)、十二烷基苯磺酸二乙二胺銅絡合物鹽[II](DBEDC)、MIF-1002(編號)、NF-180(編號)、乙酸三苯基錫(TPTA)、三苯基氯化錫(TPTC)、氫氧化三苯基錫(TPTH)、非病原性胡蘿蔔軟腐歐文菌(erwinia carotovora)、F9650(編號)。
接著,示例可混合或組合使用的已知除草劑化合物、植物生長調節劑化合物。
除草活性成分:
碘苯腈(ioxynil)、苯草醚(aclonifen)、丙烯醛(acrolein)、草芬定(azafenidin)、亞喜芬(acifluorfen)(包括與鈉等而成的鹽)、四唑嘧磺隆(azimsulfuron)、亞速爛(asulam)、乙草胺(acetochlor)、草脫淨(atrazine)、莎稗磷(anilofos)、胺唑草酮(amicarbazone)、醯嘧磺隆(amidosulfuron)、氨基三唑(amitrole)、氯丙嘧啶酸(aminocyclopyrachlor)、氯氨吡啶酸(aminopyralid)、甲基胺草磷(amiprofos-methyl)、草殺淨(ametryn)、拉草(alachlor)、亞汰草(alloxydim)、嘧啶醇(ancymidol)、愛速隆(isouron)、異噁氯草酮(isoxachlortole)、異噁唑草酮(isoxaflutole)、異惡醯草胺(isoxaben)、異癸醇乙氧基化物(isodecylalkoholethoxylate)、異丙隆(isoproturon)、三唑醯草胺(ipfencarbazone)、滅草喹(imazaquin)、甲咪唑煙酸(imazapic)(包括與胺等而成的鹽)、依滅草(imazapyr)(包括異丙基胺等的鹽)、咪草酸甲酯(imazamethabenz-methyl)、甲氧咪草煙(imazamox)、咪草煙(imazethapyr)、依速隆(imazosulfuron)、茚草胺(indaziflam)、茚草酮(indanofan)、乙基甘草津(eglinazine-ethyl)、戊草丹(esprocarb)、甲基胺苯磺隆(ethametsulfuron-methyl)、乙丁烯氟靈(ethalfluralin)、磺噻隆(ethidimuron)、亞速隆(ethoxysulfuron)、乙基氯氟草醚(ethoxyfen-ethyl)、乙氧呋草黃(ethofumesate)、乙氧苯草胺(etobenzanid)、艾匹芬西(epyrifenacil)、橋氧酞鈉(endothal-disodium)、樂滅草(oxadiazon)、丙惡唑草(oxadiargyl)、噁嗪草酮(oxaziclomefone)、オキサスルフロン(oxasulfuron)、復祿芬(oxyfluorfen)、歐拉靈(oryzalin)、嘧苯胺磺隆(orthosulfamuron)、坪草丹(orbencarb)、油酸(oleic acid)、苯酮唑(cafenstrole)、乙基克繁草(carfentrazone-ethyl)、卡草靈(karbutilate)、草長滅(carbetamide)、快伏草(quizalofop)、乙基快伏草(quizalofop-ethyl)、快伏草(quizalofop-p-ethyl)、快伏草(quizalofop-p-tefuryl)、莫克草(quinoclamine)、快克草(quinclorac)、喹草酸(quinmerac)、苄草隆(cumyluron)、氯醯草膦(clacyfos)、嘉磷塞(glyphosate)(包含鈉、鉀、胺、丙胺、異丙胺、二甲胺或三甲基硫鹽等的鹽)、固殺草(glufosinate)(包含胺或鈉等的鹽)、精固殺草(glufosinate-p)、精固殺草鈉鹽(glufosinate-p-sodium)、剋草同(clethodim)、炔草酯(clodinafop-propargyl)、畢克草(clopyralid)、可滅蹤(clomazone)、甲氧除草醚(chlomethoxyfen)、克普草゚(clomeprop)、甲基氯酯磺草胺酸(cloransulam-methyl)、克爛本(chloramben)、氯草敏(chloridazon)、氯嘧磺隆乙酯(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、氯酞酸二甲脂(chlorthal-dimethyl)、草克樂(chlorthiamid)、氯鄰苯二甲醯亞胺(chlorphthalim)、甲基氯甲丹(chlorflurenol-methyl)、氯苯胺靈(chlorpropham)、滅落寧(chlorbromuron)、枯草隆(chloroxuron)、氯麥隆(chlorotoluron)、克同匹朵(ketospiradox)(包含鈉、鈣或銨等的鹽)、殺芬草(saflufenacil)、假蒟亭堿(sarmentine)、氰乃淨(cyanazine)、氨基氰(cyanamide)、達有龍(diuron)、乙醯甲草胺(diethatyl-ethyl)、汰克草(dicamba)(包含胺、二乙基胺、異丙基胺、二甘醇胺、鈉或鋰等的鹽)、草滅特(cycloate)、環殺草(cycloxydim)、雙氯磺草胺(diclosulam)、環磺隆(cyclosulfamuron)、環吡蘭尼(cyclopyranil)、環吡莫瑞(cyclopyrimorate)、二氯苯腈(dichlobenil)、精禾草靈(diclofop-p-methyl)、禾草靈(diclofop-methyl)、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-p)、敵草快(diquat)、汰硫草(dithiopyr)、環草隆(siduron)、撻乃安(dinitramine)、吲哚酮草酯(cinidon-ethyl)、西速隆(cinosulfuron)、達諾殺(dinoseb)、特樂酚(dinoterb)、丁基賽伏草(cyhalofop-butyl)、大芬滅(diphenamid)、野燕枯(difenzoquat)、吡氟草胺(diflufenican)、二氟吡隆(diflufenzopyr)、草滅淨(simazine)、吡滅芙(dimesulfazet)、二甲草胺(dimethachlor)、二甲丙乙凈(dimethametryn)、汰草滅(dimethenamid)、精二甲吩草胺(dimethenamid-p)、西草淨(simetryn)、呱草丹(dimepiperate)、噁唑隆(dimefuron)、環庚草醚(cinmethylin)、滅草靈(swep)、磺草酮(sulcotrione)、甲磺草胺((sulfentrazone)、硫復松(sulfosate)、磺醯磺(sulfosulfuron)、甲嘧磺隆甲酯(sulfometuron-methyl)、西殺草(sethoxydim)、特草定(terbacil)、汰草龍(daimuron)、沙多明A(thaxtomin a)、得拉本(dalapon)、噻草定(thiazopyr)、氟丙嘧草酯(tiafenacil)、噻酮磺隆(thiencarbazone)(包含鈉鹽、甲酯等)、第二草丹(tiocarbazil)、殺丹(thiobencarb)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、甲基噻吩磺隆(thifensulfuron-methyl)、甜菜安(desmedipham)、敵草凈(desmetryne)、特氟吡嘧(tetflupyrolimet)、欣克草(thenylchlor)、牧草胺(tebutam)、得匍隆(tebuthiuron)、得殺草(tepraloxydim)、特糠酯酮(tefuryltrione)、草淨津(terbuthylazine)、特丁淨(terbutryn)、特丁通(terbumeton)、環磺酮(tembotrione)、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、三嗪氟草胺(triaziflam)、醚苯磺隆(triasulfuron)、氟酮磺草胺(triafamone)、燕麥畏(tri-allate)、草達津(trietazine)、綠草定(triclopyr)、三氯吡氧乙酸丁氧基乙酯(triclopyr-butotyl)、三氟甲磺隆(tritosulfuron)、三氟草嗪(trifludimoxazin)、甲基氟胺磺隆(triflusulfuron-methyl)、三福林(trifluralin)、三氟啶磺隆鈉鹽(trifloxysulfuron-sodium)、甲基苯磺隆(tribenuron-methyl)、托吡雷(tolpyralate)、鈉得爛(naptalam)(包含鈉等的鹽)、萘普草(naproanilide)、滅落脫(napropamide)、右滅落脫(napropamide-m)、煙嘧磺隆(nicosulfuron)、草不隆(neburon)、氟草敏(norflurazon)、萬隆(vernolate)、福林巴拉刈二氯鹽(paraquat dichloride)、芐基氟氯吡啶酯(halauxifen-benzyl)、氟氯吡啶酯(halauxifen-methyl)、蓋草能(haloxyfop)、蓋草能-P(haloxyfop-p)、吡氟甲禾靈(haloxyfop-etotyl)、氟硝磺醯胺(halosafen)、甲基氟硝磺醯胺(halosulfuron-methyl)、比索洛宗(bixlozone)、畢克爛(picloram)、氟吡醯草胺(picolinafen)、氟吡草酮(bicyclopyrone)、雙草醚(bispyribac-sodium)、唑啉草酯(pinoxaden)、必芬諾(bifenox)、呱草磷(piperophos)、雙唑草(pyraclonil)、磺醯草吡唑(pyrasulfotole)、普芬草(pyrazoxyfen)、百速(pyrazosulfuron-ethyl)、芐草唑(pyrazolynate)、畢拉草(bilanafos)、乙基派芬草(pyraflufen-ethyl)、噠草醇(pyridafol)、嘧草硫醚鈉(pyrithiobac-sodium)、必汰草(pyridate)、環酯草醚(pyriftalid)、稗草畏(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、嘧啶硫蕃(pyrimisulfan)、嘧草醚(pyriminobac-methyl)、派羅克殺草碸(pyroxasulfone)、啶磺草胺(pyroxsulam)、棉胺寧(phenisopham)、非草隆(fenuron)、苯磺噁唑草(fenoxasulfone)、芬殺草(fenoxaprop)(含有甲基、乙基、異丙酯)、精噁唑禾草靈(fenoxaprop-p)(含有甲基、乙基、異丙酯)、芬喹三酮(fenquinotrione)、噻唑禾草靈(fenthiaprop-ethyl)、四唑醯草胺(fentrazamide)、甜菜寧(phenmedipham)、丁基拉草(butachlor)、布芬草(butafenacil)、抑草磷(butamifos)、拔敵草(butylate)、丁烯草胺(butenachlor)、比達寧(butralin)、丁苯草酮(butroxydim)、伏速隆(flazasulfuron)、甲氟燕靈(flamprop)、(包含甲基、乙基、異丙酯)、右甲氟燕靈(flamprop-m)(包含甲基、乙基、異丙酯)、甲基氟嘧磺隆(primisulfuron-methyl)、氟呱丁酯(fluazifop-butyl)、氟苯氟對丁基(fluazifop-p-butyl)、氟唑鹽(fluazolate)、氟美隆(fluometuron)、乙基乙羧氟草醚(fluoroglycofen-ethyl)、氟唑磺隆鈉鹽(flucarbazone-sodium)、氟氯林(fluchloralin)、氟嘧磺隆(flucetosulfuron)、草酸甲酯(fluthiacet-methyl)、甲基氟啶嘧磺隆(flupyrsulfuron-methyl)(包含鈉、鈣或是銨等的鹽塩)、氟噻草胺(flufenacet)、乙基氟苯吡咯(flufenpyr-ethyl)、四氟丙酸(flupropanate)、氟蟲草(flupoxame)、丙炔氟草胺(flumioxazin)、戊基氟氯吡庫(flumiclorac-pentyl)、唑嘧磺草胺(flumetsulam)、氟啶酮(fluridone)、呋草酮(flurtamone)、氟氯比(fluroxypyr)(包含如丁甲基、meptyl等之酯、鈉、鈣或銨等的鹽)、氟咯草酮(flurochloridone)、普拉草(pretilachlor)、丙卡巴肼鈉(procarbazone-sodium)、丙二胺(prodiamine)、三氟丙磺隆(prosulfuron)、芐草丹(prosulfocarb)、普拔草(propaquizafop)、雷蒙德(propachlor)、普拔根(propazine)、flupoxame除草靈(propanil)、炔苯醯草胺(propyzamide)、異丙草胺(propisochlor)、丙嗪嘧磺隆(propyrisulfuron)、苯胺靈(propham)、氟唑草胺(profluazol)、調環酸鈣(prohexadione-calcium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆鈉鹽(propoxycarbazone-sodium)、環苯草酮(profoxydim)、克草(bromacil)、溴莠敏(brompyrazon)、佈滅淨(prometryn)、撲滅通(prometon)、溴草腈(bromoxynil)(包含丁酸、辛酸或庚酸等的酯)、殺草全(bromofenoxim)、溴丁醯草胺(bromobutide)、雙氟磺草胺(florasulam)、氯氟吡啶酯(florpyrauxifen)、氯氟吡啶酯(florpyrauxifen-benzyl)、菲殺淨(hexazinone)、烯草胺(pethoxamid)、草除靈(benazolin)、平速爛(penoxsulam)、庚醛木葡聚醣(heptamaloxyloglucan)、氟丁醯草胺(beflubutamid)、右氟丁醯草胺(beflubutamid-m)、克草猛(pebulate)、壬酸(pelargonic acid)、醯苯草酮(bencarbazone)、施得圃(pendimethalin)、雙苯嘧草酮(benzfendizone)、地散磷(bensulide)、甲基苄嘧黃隆(bensulfuron-methyl)、苯並雙環酮(benzobicyclon)、吡草酮(benzofenap)、苯達松(bentazone)、甲氯醯草胺(pentanochlor)、噁草酮(pentoxazone)、倍尼芬(benfluralin)、吠草黃(benfuresate)、殺木膦(fosamine)、氟磺胺草醚(fomesafen)、甲醯胺磺隆(foramsulfuron)、福芬素(forchlorfenuron)、二甲四氯丙酸(mecoprop)(含有鈉、鉀、異丙基胺、三乙醇胺、二甲基胺等的鹽)、二甲四氯丙酸對鉀鹽(mecoprop-p-potassium)、磺胺磺隆(mesosulfuron)(含有甲基等之酯)、甲基磺草酮(mesotrione)、滅草胺(metazachlor)、雙醚氯吡嘧磺隆(metazosulfuron)、噻唑隆(methabenzthiazuron)、苯嗪草酮(metamitron)、唑醯草胺(metamifop)、斯美地(metam)、甲烷磺酸二鈉(dsma)、噻草醚(methiozolin)、甲基迪慕隆(methyldymuron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲磺隆(metsulfuron-methyl)、撲奪草(metobromuron)、吡喃隆(metobenzuron)、莫多草(metolachlor)、滅必淨(metribuzin)、縮節胺(mepiquat chloride)、滅芬草(mefenacet)、單嘧磺酯(monosulfuron)(含有甲基、乙基、異丙基酯)、綠穀龍(monolinuron)、稻得壯(molinate)、碘磺隆(iodosulfuron)、碘甲磺隆鈉鹽(iodosulfulon-methyl-sodium)、碘苯磺隆(iofensulfuron)、碘苯磺隆鈉鹽(iofensulfuron-sodium)、乳氟禾草靈(lactofen)、蘭蔻三酮(lancotrione)、理有龍(linuron)、玉嘧磺隆(rimsulfuron)、環草定(lenacil)、2,2,2-三氯乙酸(TCA)(含有鈉、鈣或銨等的鹽)、2,3,6-三氯苯甲酸(2,3,6-TBA)、2,4,5-三氯苯氧基乙酸(2,4,5-T)、2,4-二氯苯氧基乙酸(2,4-D)(含有胺、二乙基胺、三乙醇胺、異丙基胺、鈉或鋰等的鹽)、2-氨基-3-氯-1,4-萘醌(ACN)、2-甲基-4-氯苯氧基乙酸(MCPA)(含有鈉鹽、乙基酯等)、2-甲基-4-氯苯氧基丁酸(MCPB)(含有鈉塩、乙基酯等)、4-(2,4-二氯苯氧基)丁酸(2,4-DB)、4,6-二硝基-O-甲酚(DNOC)(含有胺或鈉等之鹽)、AE-F-150944(編號)、IR-6396(編號)、硫乙基MCPA(mcpa-thioethyl)、SYP-298(編號)、SYP-300(編號)、S-乙基二丙基氨基甲酸酯(eptc)、左旋莫多草(s-metolachlor)、S-9750(編號)、MSMA(MSMA)、HW-02(編號)、NC-653(編號)、S-523(編號)、SL-1201(編號)。
植物生長調節劑:
1-萘乙醯胺(1-naphthylacetamide)、1-甲基環丙烯(1-methylcyclopropene)、2,6-二異丙基萘(2,6-diisopropylnaphthalene)、4-氧代-4-(2-苯基乙基)氨基丁酸(化學名稱、CAS登錄編號:1083-55-2)、4-氯苯氧基乙酸(4~Cpa)、正癸醇(n-decanol)、艾維激素(aviglycine)、嘧啶醇(ancymidol)、離層酸(abscisic acid)、依納素(inabenfide)、吲哚乙酸(indole acetic acid)、吲哚丁酸(indole butyric acid)、單克素(uniconazole)、單克素-p(uniconazole-p)、艾各犁(ecolyst)、吲熟酯(ethychlozate)、益收生長素(ethephon)、艾波連(epocholeone)、硫酸辛酸(oxine-sulfate)、香芹酮(carvone)、甲酸鈣(calcium formate)、座果酸(cloxyfonac)、座果酸鉀鹽(cloxyfonac-potassium)、調果酸(cloprop)、克美素(chlormequat)、膽鹼(choline)、細胞分裂素(cytokinins)、環丙醯草(cyclanilide)、敵草克(dikegulac)、赤黴酸(gibberellin acid)、穫萎得(dimethipin)、殺雄啉(sintofen)、丁醯肼(daminozide)、苯基噻二唑基脲(thidiazuron)、三十醇(triacontanol)、抗倒酯(trinexapac-ethyl)、多效唑(paclobutrazol)、石蠟(paraffin)、氟節胺(flumetralin)、呋嘧醇(flurprimidol)、抑草丁(flurenol)、前尼替丁(pronitridine)、茉莉酸丙酯(prohydrojasmon)、調環酸鈣鹽(prohexadione-calcium)、七醛氧化葡聚醣(heptamaloxyloglucan)、芐氨基嘌呤(benzylaminopurine)、氯吡脲(forchlorfenuron)、順丁烯二醯肼(maleic hydrazide)、縮節胺(mepiquat chloride)、美福泰(mefluidide)、過氧化鈣。
接著,示例可混合或組合使用的已知減輕藥害化合物。
異噁二芬(isoxadifen)、乙基異噁二芬(isoxadifen-ethyl)、解草腈(oxabetrinil)、解毒(cloquintcet-mexyl)、增效磷(dietholate)、解草胺腈(cyometrinil)、二氯丙烯胺(dichlormid)、鹽酸雙環胺(dicyclonone)、賽普磺醯胺(cyprosulfamide)、1,8-萘二甲酸酐(1,8-naphthalic anhydride)、解草唑(fenchlorazole-o-ethyl)、解草啶(fenclorim)、解草惡唑(furilazole)、氟所芬寧(fluxofenim)、抑草丁(flurazole)、解草酮(benoxacor)、氯苯基胺基甲酸甲酯(mephenate)、吡唑解草酯(mefenpyr)、乙基吡唑解草酯(mefenpyr-ethyl)、二乙基吡唑解草酯(mefenpyr-diethyl)、低級烷基取代苯甲酸、2,2-二氯-n-(1,3-二氧戊環-2-基甲基)-n-(2-丙炔)乙醯胺(PPG-1292)、2-二氯甲基-2-甲基-1,3-二惡烷(mg-191)、3-二氯乙醯基-2,2,5-三甲基-1,3-噁唑烷(R-29148)、4-二氯乙醯基-1-氧雜-4-氮雜螺[4.5]癸烷(ad-67)、MON4660(編號)、梅卡芬(metcamifen)、N1,N2-二烯丙基-N2-二氯乙醯基甘氨醯胺(DKA-24)、TI-35(編號)。
如上述般構成的本發明之有害生物防治劑對以下有害生物具有優異的防治效果:直翅目害蟲、纓翅目害蟲、半翅目害蟲、鞘翅目害蟲、雙翅目害蟲、鱗翅目害蟲、膜翅目害蟲、彈尾目害蟲、纓尾目害蟲、蜚蠊目害蟲、囓蟲目害蟲、革翅目害蟲、食毛目害蟲、虱毛目、植物寄生性蟎類、植物寄生性線蟲類、植物寄生性軟體動物、其他有害動物、危害型動物、衛生害蟲、寄生蟲等有害生物。如此的有害生物的實例包括以下物種。
作為直翅目害蟲,可列舉例如:螽斯科的俄羅斯線蟲(Ruspolia lineosa);蟋蟀科的黃臉油葫蘆(Teleogryllus emma)、綠蛣蛉(Truljalia hibinonis);螻蛄科的東方螻蛄(Gryllotalpa orientalis);蝗科的小稻蝗(Oxya hyla intricate)、飛蝗(Locusta migratoria)、遷徙螞蚱(Melanoplus sanguinipes)、殊種蝗(Melanoplus differentialis)、紅腿蝗蟲(Melanoplus femurrubrum)、尖頭蝗(Atractomorpha lata);叢蟋科的日本叢蟋(Euscyrtus japonicus)、蚤蝗科的日本蚤螻(Xya japonicus)等。
作為纓翅目害蟲,可列舉例如:薊馬科的台灣花薊馬(Frankliniella intonsa)、西部花薊馬(Frankliniella occidentalis)、小黃薊馬(Scirtothrips dorsalis)、棕櫚薊馬(Thrips palmi)、蔥薊馬(Thrips tabaci)、日本菸草薊馬(Thrips setosus)、變葉木薊馬(Heliothrips haemorrhoidalis)、稻薊馬(Stenchaetothrips biformis)等;管薊馬科的柿管薊馬(Ponticulothrips diospyrosi)、芥末滑管薊馬(Liothrips wasabiae)、稻管薊馬(Haplothrips aculeatus)等。
作為半翅目害蟲,可列舉例如:蟬科的姬草蟬(Mogannia minuta)等;沫蟬科的白帶尖胸沫蟬(Aphrophora intermedia)、甘蔗沫蟬(Mahanarva fimbriolata)等;角蟬科的褐角蟬(Machaerotypus sibiricus)等;角頂葉蟬科的葡萄二星葉蟬(Arboridia apicalis)、小綠葉蟬(Empoasca onukii)、偽黑尾葉蟬(Nephotettix cincticeps)、馬來亞黑尾葉蟬(Nephotettix malayanus)、二點黑尾葉蟬(Nephotettix virescens)、黑條黑尾葉蟬(Ephotettix nigropictus)、電光紋葉蟬(Recilia dorsalis)、二點小綠葉蟬(Amrasca biguttula)、檬果褐葉蟬(Idioscopus nitidulus、Idioscopus clypealis、Amritodus atkinsoni)、馬鈴薯小綠葉蟬(Empoasca fabae)、玉米葉蟬(Albulus maidis)等;菱飛蝨科的五胸脊菱臘蝶(Pentastiridius apicalis)等;稻蝨科的斑飛蝨(Laodelphax striatellus)、褐飛蝨(Nilaparvata lugens)、白背飛虱(Sogatella furcifera)、玉米飛蝨(Peregrinus maidis)等;雪白粒脈蠟蟬科的雪白粒脈蠟蟬(Nisia nervosa)等;長翅飛蝨科的卡曼答卡飛蝨(Kamendaka saccharivora)等;小頭飛蝨科的紅木耳蟲(Achilus flammeus)等;廣翅蠟蟬科的日本蠟蟬(Orosanga japonicus)等;青翅飛蝨科的蛾蠟蟬(Mimophantia maritima)等;木蝨科的梨糖木(Cacopsylla pyrisuga)、柑橘木蝨(Diaphorina citri)等;麗木蝨科的檬果麗木蝨(Calophya mangiferae)等;根瘤蚜科的葡萄根瘤蚜(Daktulosphaira vitifoliae)等;球蚜科的落葉松球蚜(Adelges laricis)、鐵杉球蚜蟲(Adelges tsugae)等;蚜科的豌豆蚜(Acyrthosiphon pisum)、綿蚜(Aphis gossypii)、橘捲葉蚜(Aphis spiraecola)、偽菜蚜(Lipaphis erysimi)、菜蚜 (Brevicoryne brassicae)、桃蚜(Myzus persicae)、麥二叉蚜(Schizaphis graminum)、稻麥蚜(Rhopalosiphum padi)、小桔蚜(Toxoptera aurautii)、馬鈴薯蚜(Aulacorthum solani)、桃蚜(Macrosiphum euphorbiae)、萵苣蚜蟲(Nasonovia ribisnigri)、麥長管蚜(Sitobion avenae)、大豆蚜(Aphis glycines)等;粉蝨科的茶刺粉蝨(Aleurocanthus camelliae)、柑桔刺粉蝨(Aleurocanthus spiniferus)、煙草粉蝨(Bemisia tabaci)、銀葉粉蝨(Bemisia argentifolii)、溫室粉虱(Trialeurodes vaporariorum)等;綿介殼蟲科的草履蚧(Drosicha corpulenta)、吹綿介殼蟲(Icerya purchasi)等;粉介殼蟲科的鳳梨粉介殼蟲(Dysmicoccus brevipes)、臀紋粉介殼蟲(Planococcus citri)、康氏粉介殼蟲(Pseudococcus comstocki)等;介殼蟲科的角蠟蟲(Ceroplastes ceriferus)、紅蠟蟲(Ceroplastes rubens)等;仁介殼蟲科的甘蔗仁介殼蟲(Aclerda takahashii)等;盾介殼蟲科的橘紅腎圓盾介殼蟲(Aonidiella aurantii)、梨齒盾介殼蟲(Diaspidiotus perniciosus)、桑擬白輪盾介殼蟲(Pseudaulacaspis pentagoa)、箭頭介殼蟲(Unaspis yanonensis)等;盲蝽科的美洲牧草盲蝽(Lygus lineolaris)、赤鬚盲蝽(Trigonotylus caelestialium)、綠盲蝽(Apolygus lucorum)、菸盲椿(Nesidiocoris tenuis)、庭園盲蝽(Halticus bractatus)等;網蝽科的杜鵑冠網蝽(Stephanitis pyrioides)、梨冠網蝽(Stephanitis nashi)等;蝽象科的甘藍菜蝽(Eurydema rugosa)、日本二星蝽(Eysarcoris lewisi)、北二星蝽(Eysarcoris aeneus)、稻褐蝽(Lagynotomus elongatus)、稻綠蝽(Nezara viridula)、小珀蝽(Plautia crossota)、花角綠蝽(Nezara antennata)、褐蝽(Eushistus heros)、紅帶椿象(Piezodorus guildini)、甘藍菜蝽(Tibraca limbativentris)、綠腹臭蟲(Dichelops furcatus)等;龜蝽科的篩豆龜椿(Megacopta cribraria)等;異尾蝽科的黎龜蝽(Urochela luteovoria)等;長蝽科的小翅椿象(Cavelerius saccharivorus)等;毛蝽科的日本毛蝽(Malcus japonicus)等;紅蝽科的離斑棉紅蝽(Dysdercus cingulatus)等;蛛緣蝽科的禾蛛緣椿象(Leptocorisa acuta)、中稻緣蝽(Leptocorisa chinensis)等;緣蝽科的紋須同緣蝽(Anacanthocoris striicornis)等;姬緣椿科的黃伊緣蝽(Rhopalus maculatus)等;土蝽科的根土蝽(Scaptocoris castanea)等;臭蟲科的溫帶臭蟲(Cimex lectularis)等。
作為鞘翅目害蟲,可列舉例如:金龜子科的銅金龜屬(Anomara cuprea)、多色異麗金龜(Anomara rufocuprea)、日本弧麗金龜(Popillia japonica)、小青花金龜(Oxycetonia jucunda)、椎花金龜(Anomala geniculata)、椰子犀角金龜(Oryctes rhinoceros)、茶色長金龜(Heptophylla picea)、六月金龜(Phyllophaga cuyabana)等、叩頭蟲科的蛄雷扣甲(Agriotes ogurae)、細胸金針叩甲(Agriotes lineatus)、暗紋叩甲(Agriotes obscurus)、沖繩扣甲(Melanotus okinawensis)、紅薯梳爪扣甲(Melanotus fortnumi)等;鰹節蟲科的姬圓鰹節蟲(Anthrenus verbasci)等;長蠹蟲科的二突異翅長蠹蟲(Heterobostrychus hamatipennis)等;食骸蟲科的藥材甲蟲(Stegobium paniceum)等;蛛甲科的扁蛛甲(Pitinus clavipes)等;擬榖盜科的大穀盜(Tenebroides mauritanicus)等;郭公蟲科的赤足郭公蟲(Necrobia rufipes)等;露尾甲科的露尾甲乾果甲蟲(Carpophilus hemipterus)、油菜露尾甲(Meligethes aeneus)等;細扁甲科的背圓粉扁蟲(Ahasverus advena)等;扁甲甲蟲科的角胸粉扁蟲(Cryptolestes ferrugineus)等;瓢蟲科的墨西哥豆甲蟲(Epilachna varivestis)、茄二十八星瓢蟲(Henosepilachna vigintioctopunctata)等;擬步行蟲科的黃粉蟲(Tenebrio molitor)、赤擬穀盜(Tribolium castaneum)等;地膽科的豆芫菁(Epicauta gorhami)等;天牛科的光肩星天牛(Anoplophora glabripennis)、葡萄虎天牛(Xylotrechus pyrrhoderus)、松墨天牛(Monochamus alternatus)、大豆莖螟蟲(Dectes texanus)等;豆象的綠豆象(Callosobruchus chinensis)等;金花蟲科的科羅拉多金花蟲(Leptinotarsa decemlineata)、玉米根葉甲(Diabrotica virgifera virgifera)、北部玉米根蟲(Diabrotica barberi)、斑點黃瓜甲蟲(Diabrotica undecimpunctata howardi)、黃守瓜蟲(Aulacophora femoralis)、小猿葉蟲(Phaedon brassicae)、甜菜大龜甲(Cassida nebulosa)、稻負泥蟲(Oulema oryzae)、墨西哥豆甲蟲(epilachna varivestis)、黃條葉蚤(Phyllotreta striolata)、茶肖葉甲(Demotina fasciculata)、菜莖跳甲(Psylliodes chrysocephala)、菜豆螢葉甲(Cerotoma trifurcate)、葡萄肖葉甲(Colaspis brunnea)、克裡尼肖葉甲(Colaspis crinnicornis)、大豆潛葉蛾(Odontota horni)、三葉草跳蚤甲蟲(Chaetocnema pulicaria)、帶狀黃瓜甲蟲(Diabrotica balteata)等;三錐象鼻蟲科的甘藷蟻象(Cylas formicarius)等;象鼻蟲科的苜蓿象鼻蟲(hypera postica)、蔬菜象鼻蟲(Listroderes costirostris)、 西印度甘薯象鼻蟲(Euscepes postfasciatus)、板栗象鼻蟲(Curculio sikkimensis)、棉子象鼻蟲(Anthonomus grandis)、大豆莖象鼻蟲(Sternechus subsignatus)等;粗吻象鼻蟲科的稻象鼻蟲(Echinocnemus bipunctatus)、水稻水象鼻蟲(Lissorhoptrus oryzophilus)、稻象甲(Oryzophagus oryzae)等;象甲科的玉米象(Sitophilus zeamais)、獵長喙象(Sphenophrus venatus)、甘蔗象(Sphenophorus levis)等;小蠹亞科的縱坑切梢小蠹(Tomicus piniperda)等;長小蠢科的臺日截尾長小蠹(Crossotarsus niponicus)等;扁蠹蟲科的褐粉蠹(Lyctus brunneus)等。
作為雙翅目害蟲,可列舉例如:大蚊科的稻大蚊(Tipula aino)等;毛蠅科的毛蚋(Plecia nearctica)等;蕈蠅科的茸蕈蠅(Exechia shiitakevora)等;黑翅蕈蚋科的馬鈴薯蕈蚊(Pnyxia scabiei)、拓果實蠅(Bradysia agrestis)等;癭蚋科的大豆莢癭蚊(Asphondylia yushimai)、黑森癭蚊(Mayetiola destructor)、藍莓癭蚊(Dasineura oxycoccana)等;蚊科的埃及斑蚊(Aedes aegypti)、淡色庫蚊(Culex pipiens pallens)等;蚋科的高橋氏蚋(Simulium takahashii)等;搖蚊科的雙翅目稻搖蚊(Chironomus oryzae)等;虻科的密斑虻(Chrysops suavis)、牛虻(Tabanus trigonus)等;食蚜蠅科的洋蔥平顏蚜蠅(Eumerus strigatus)等;果實蠅科的東方果實蠅(Bactrocera dorsalis)、日本果實蠅(Euphranta japonica)、地中海果實蠅(Ceratitis capitata)等;潛蠅科的非洲菊斑潛蠅(Liriomyza trifolii)、蔬菜斑潛蠅(Liriomyza sativae)、日本稻潛蠅(Agromyza oryzae)、番茄斑潛蠅(Liriomyza bryoniae)、菜園彩潛蠅(Chromatomyia horticola)、蔥潛蠅(LirIomyza chinensis)等;稈蠅科的黑麥稈蠅(Meromyza nigriventris)等;果蠅科的鈴木氏果蠅(Drosophila suzukii)、黑腹果蠅(Drosophila melanogaster)等;水蠅科的水稻潛葉蠅(Hydrellia griseola)等;蝨蠅科的馬虱蠅(Hippobosca equina)等;糞蠅科的笹川氏糞蠅(Parallelpmma sasakawae)等;花蠅科的洋蔥蠅(Delia antiqua)、歐洲花蠅(Delia platura)等;夏廁蠅科的夏廁蠅(Fannia canicularis)等;家蠅科的家蠅(Musca domestica)、螫蠅(Stomoxys calcitrans)等;麻蠅科的遊蕩肉蠅(Sarcophaga peregrina)等;馬蠅科的馬蠅(Gasterophilus intestinalis)等;牛蠅科的牛蠅(Hypoderma lineatum)等;羊蠅科的羊蠅(Oestrus ovis)等。
作為鱗翅目害蟲,可列舉例如:淡緣蝠蛾科的淡緣蝠蛾(Endoclita excrescens)等;日蛾科的葡萄豔蛾(Antispila ampelopsia)等;蠹蛾科的六星黑點豹蠹蛾(Zeuzera leuconotum)、芳香木蠹蛾(Cossus insularis)等;捲葉蛾科的亂紋蘋果捲葉蛾(Archips fuscocupreanus)、棉褐帶捲葉蛾(Adoxophyes orana fasciata)、桃折心蟲(Grapholita molesta)、茶捲葉蛾(Homona magnanima)、大豆食心蟲(Leguminivora glycinivorella)、黑姬捲葉蛾(Cydia pomonella)、葡萄藤蛾(Lobesia botrana)等;細捲葉蛾科的葡萄與蘋果捲葉蛾(Eupoecilia ambiguella)等;蓑蛾科的蓑蛾(Bambalina sp.)、微型大蓑蛾(Eumeta minuscula)等;蕈蛾科的穀蛾(Nemapogon granella)、衣蛾(Tinea translucens)等;稜巢蛾科的梨角折蛾(Bucculatrix pyrivorella)等;潛蛾科的桃潛葉蛾(Lyonetia clerkella)、青枯葉蛾(Lyonetiaprunifoliella malinella)等;細蛾科的茶細蛾(Caloptilia theivora)、金紋小潛細蛾(Phyllonorycter ringoniella)等;小潛蛾科的柑橘潛蛾(Phyllocnistis citrella)等;偽菜蛾科的蔥菜蛾(Acrolepiopsis sapporensis)等;菜蛾科的小菜蛾(Plutella xylostella);巢蛾科的蘋果巢蛾(Yponomeuta orientalis)等;銀蛾科的蘋實銀蛾(Argyresthia conjugella)等;透翅蛾科的葡萄透翅蛾(Nokona regalis)、茶藨子透翅蛾(Synanthedin hector)等;鱗翅目蛾科的馬鈴薯塊莖蛾(Phthorimaea operculella)、麥蛾(Sitotroga cerealella)、棉紅鈴蟲(Pectinophora gossypiella)、番茄斑潛蠅(Tuta absoluta)等;果蛀蛾科的桃蛀果蛾(Carposina sasakii)等;斑蛾科的梨星毛蟲(Illiberis pruni)等;刺蛾科的黃刺蛾(Monema flavescens)等;草螟科的稻巢草螟(Ancylolomia japonica)、二化螟(Chilo suppressalis)、稻縱捲葉野螟(Cnaphalocrocis medinalis)、亞洲玉米螟(Ostrinia furnacalis)、菜心螟(Hellulla undalis)、桃蛀野螟蛾(Conogethes punctiferlis)、瓜絹野螟蛾(Diaphania indica)、藍草螟蛾(Parapediasia teterrella)、歐洲玉米螟(Ostrinia nubilalis)等、蔗螟(Diatraea saccharalis);螟蛾科的粉斑螟蛾(Cadra cautella)、大蠟蛾(Galleria mellonella)等;羽蛾科的葡萄日羽蛾(Nippoptilia vitis)等;鳳蝶科的柑橘鳳蝶(Papilio xuthus)等;粉蝶科的白粉蝶(Pieris rapae)等;弄蝶科的稻弄蝶(Parnara guttata);尺蛾科的腎斑尺蛾(Ascotis selenaria)等;枯葉蛾科的赤松毛蟲(Dendrolimus spectabilis)、天幕毛蟲(Malacosoma neustrium testaceum)等;天蛾科的白薯天蛾(Agrius convolvuli)等;裳蛾科的茶毒蛾(Arna pseudoconspersa)、旋古毒蛾(Orygia recens approximans)、舞毒蛾(Lymantria dispar)等;豹燈蛾的美國白蛾(Hyphantria cunea)等;夜蛾科的小地老虎(Agrotis ipsilon)、黃地老虎(Agrotis segetum)、黑點銀紋夜蛾(Autographa nigrisigna)、番茄夜蛾(Helicoverpa armigera)、玉米穗蟲(Helicoverpa zea)、菸芽夜蛾(Heliothis virescens)、甜菜夜蛾(Spodoptera exigua)、斜紋夜盜蛾(Spodoptera litura)、大豆尺蠖(Chrysodeix includens)、草地夜蛾(Spodoptera frugiperda)、青銅地蠶(Nephelodes minians)等。
作為膜翅目害蟲,可列舉例如:三節葉蜂科的玫瑰黃腹三節葉(Arge pagana)等;葉蜂科的栗葉蜂(Apethymus kuri)、紅角菜葉蜂(Athalia rosae ruficornis)等;癭蜂的板栗癭蜂(Dryocosmus kuriphilus)等;胡蜂科的黃色胡蜂(Vespa Simillima xanthoptera)等;蟻科的紅火蟻(Solenopsis invicta)、阿根廷蟻(Linepithema humile)等;切葉蜂科的薔薇切葉蜂(Megachile nipponica)等。
作為彈尾目害蟲,可列舉例如圓跳蟲科的黃星圓跳蟲(Bourletiella hortensis)等。
作為纓尾目害蟲,可列舉例如衣魚科的衣魚(Lepisma saccharina)、絨毛衣魚(Ctenolepisma villosa)等。
作為蜚蠊目害蟲,可列舉例如:美洲蜚蠊(Periplaneta americana);姬蜚蠊科的德國姬蠊(Blattella germanica);木白蟻科的台灣黑翅土白蟻(Odontotermes formosanus);白蟻科的小楹白蟻(Incisitermes minor)、截頭堆砂白蟻(Cryptotermes domesticus);細白蟻科的臺灣家白蟻(Coptotermes formosanus)、散白蟻(Reticulitermes speratus)等。
作為囓蟲目害蟲,可列舉例如:節嚙蟲科的粉茶蛀蟲(Trogium pulsatorium)等;虱齧科的書蝨(Liposcelis corrodens)等。
作為革翅目害蟲,可列舉例如蠼螋科的岸蠼螋(Labodura riparia)等。
作為食毛目害蟲害蟲,可列舉例如短角羽蝨科的翼蝨(Lipeurus caponis)等;獸羽蝨科的牛蝨(Damalinia bovis)等。
作為虱毛目害蟲,可列舉例如獸蝨科的豬蝨(Haematopinus suis)等;人蝨科的人蝨(Pediculus humanus)等;鄂虱科的吸蝨(Linognathus setosus)等;陰蝨科的陰蝨(Pthirus pubis)等。
作為蟎目害蟲,可列舉例如:真足蟎科的粗足粉蟎(Penthaleus major)等;細蟎科的櫻草植食蟎(Phytonemus pallidus)、多食細蟎(Polyphagotarsonemus latus)等;擬蟎科的蒲蟎的一種(Siteroptes sp.)等;偽葉蟎科的葡萄短須蟎(Brevipalpus lewisi)等;杜克葉蟎科的孔雀葉蟎(Tuckerella pavoniformis)等;葉蟎科的北始葉蟎(Eotetranychus boreus)、柑橘葉蟎(Panonychus citri)、歐洲紅蟎(panonychus ulmi)、二斑葉蟎(Tetranychus urticae)、神澤氏葉蟎(Tetranychus kanzawai)等;納氏癭蟎科的松三毛癭蟎(Trisetacus pini)等;節蜱科的桔刺皮節蜱(Aculops pelekassi)、梨銹蜱(Epitrimerus pyri)、柑橘銹蟎(Phyllocoptruta oleivora)、番茄銹蟎(Aculops lycopersici)等;雙羽爪節蜱科的圓鋸齒蟎(Diptacus crenatae)等;粉蟎科的粉蟎(Aleuroglyphus ovatus)、腐食酪蟎(Tyrophagus putrescentiae)、羅賓根蟎(Rhizoglyphus robini);瓦蟎科的大蜂蟎(Varroa jacobsoni)等;皮刺蟎科的雞皮刺蟎(Dermanyssus gallinae)等;巨刺蟎科的北方禽蟎(Ornithonyssus sylviarum)等;硬蜱科的微小牛蜱(Boophilus microplus)、血紅扇頭蜱(Rhipicephalus sanguineus)、長角血蜱(Haemaphysalis longicornis)等;疥蟎科的人疥蟎(Sarcoptes scabiei)等。
作為植物寄生性線蟲類,可列舉例如:長針科的劍線蟲(Xiphinema index)等;毛刺科的較小擬毛刺線蟲(Paratrichodorus minor)等;小桿科的一種小桿線蟲(Rhabditella sp.)等;墊刃科(Tylenchida)的一種墊刃線蟲(Aglenchus sp.)等;錐墊刃科(Tylodoridae)的一種頭茅線蟲(Cephalenchus sp.)等;粒科的草莓線蟲(Nothotylenchus acris)、馬玲薯腐敗線蟲(Ditylenchus destructor)等;紐帶科的腎形線蟲(Rotylenchulus reniformis)、螺旋線蟲(Helicotylenchus dihystera)等;根腐科的彎曲短體線蟲(Paratylenchus curvitatus)等;根瘤科的南方根瘤線蟲(Meloidogyne incognita)、水稻根瘤線蟲(Meloidogyne hapla)、爪哇根瘤線蟲(Meloidogyne javanica)、奇氏根瘤線蟲(Meloidogyne chitwoodi)、偽根瘤線蟲(Meloidogyne fallax)等;異皮科的黃金線蟲(Globodera rostochiensis)、馬鈴薯胞囊線蟲(Globodera pallida)、大豆胞囊線蟲(Heterodera glycines)、甜菜孢囊線蟲(Heterodera schachtii)等;端墊刃科(Telotylenchidae)的矮化線蟲(Tylenchorhynchus claytoni)等;平滑墊刃科的螺旋線蟲的一種平滑墊刃線蟲(Psilenchus sp.)等;環科的環紋線蟲類的一種(Criconemoides sp.)等;半穿刺科的半穿刺線蟲(Tylenchulus semipenetrans)等;球線蟲科的山茶球線蟲(Sphaeronema camelliae)等;短體科的嗜柑橘穿孔線蟲(Radopholus citrophilus)、香蕉穿孔線蟲(Radopholus similis)、假根瘤線蟲(Nacobbus aberrans)、穿刺短體線蟲(Pratylenchus penetrans)、咖啡短體線蟲(Pratylenchus coffeae)、玉米短體線蟲(Pratylenchus zeae)、短尾短體線 蟲(Pratylenchus brachyurus)等;小齒線蟲科的傘菌褶瘤線蟲(Iotonchium ungulatum)等;滑刃科的滑刃線蟲(Aphelenchus avenae)等;葉芽科的水稻葉芽線蟲(Aphelenchoides besseyi)、草莓葉枯線蟲(Aphelenchoides fragariae)等;寄生滑刃科的松材線蟲(Bursaphelenchus xylophilus)等。
作為植物寄生性軟體動物,可列舉例如:福壽螺科的福壽螺(Pomacea canaliculata)等;皺足蛞蝓科的高突足襞蛞蝓(Leavicaulis alte)等;非洲大蝸牛科的非洲大蝸牛(Achatina fulica)等;蛞蝓科的雙線蛞蝓(Meghimatium bilineatum)等;琥珀蝸牛科的琥珀蝸牛(Succinealauta)等;淺圓盤螺科的淺圓盤螺(Discus pauper)等;帶螺科的蝦夷帶螺(Zonitoides yessoensis)等;背盾蛞蝓科的黃蛞蝓(Limax flavus)、瓦倫西亞列蛞蝓(Lehmannia valentiana)、網紋野蛞蝓 (Deroceras reticulatum)等;鱉甲蝸牛科的哈裡木鱉甲蝸牛(Parakaliella harimensis)等;扁蝸牛科的琉球球蝸牛(Acusta despecta sieboldiana)、同型巴蝸牛(Bradybaena similaris)等。
作為其他有害動物、危害型動物、衛生害蟲、寄生蟲等有害生物,可列舉例如:十足目蝲蛄科的克氏原螯蝦(Procambarus clarkii)等;等足目的足目鼠婦科的糙瓷鼠婦(Porcellio scaber)等;球鼠婦科的鼠婦(Armadillidium vulgare)等;蚰蜒目蚰蜒科的為花蚰蜒(Thereuonema tuberculata)或蜈蚣目哈氏蜈蚣(Scolopendra subspinipes)等之唇足綱害蟲、帶馬陸目奇馬陸科的溫室馬陸(Oxidus gracilis)等的倍足綱害蟲、蜘蛛目姬蛛科的哈氏球蛛(Theridiidae hasseltii)等;蜘蛛目囊蜘蛛科的日本紅螯蛛(Cheiracanthium japonicum)等、蠍目的土耳其黑肥尾蠍ー(Androctonus crassicauda)等;屬於線形動物內部寄生蟲之蛔蟲類(Ascaris lumbricoides)等;鼠蟯蟲類(Syphacia sp.)等;血絲蟲類的班氏絲蟲(Wuchereria bancrofti)等;屬於扁形動物內部寄生蟲的肝吸蟲(Distomum sp.)、衛氏肺吸蟲(Paragonimus westermanii)、橫川後殖吸蟲(Metagonimus yokokawai)、日本血吸蟲(Schistosoma japonicum)、肉絛蟲(Taenia solium)、肥胖帶吻絛蟲((Taeniarhynchus saginatus)、包絛蟲(Echinococcus sp.)、廣節裂頭絛蟲(Diphyllobothrium latum)等。
本發明之有害生物防治劑對於已經對現存有害生物防治劑具有抗性之前述示例的有害生物等也呈現出防治效果。另外,本發明之有害生物防治劑也可使用於透過基因重組、人工交配等而獲得抗害蟲性、抗病性、抗除草劑性等特性之植物。
本發明之「透過基因重組、人工交配等而被賦予抗性之植物」並非僅指基於典型的育種交配所進行之賦予抗性、基因重組技術而達到的抗性之賦予,還包括將現有交配技術中的分子生物學手法進行組合而得的新育種技術(New Plant Breeding Techniques, NBTs)而賦予抗性之植物。新育種技術(NBTs)係記載於「讓我們瞭解新的植物育種技術」(國際文獻公司,大澤良、江面浩著),評論文章「植物中的基因組編輯工具(Genome Editing Tools in Plants)」(Genes 2017,8, 399,Tapan Kumar Mohanta、Tufail Bashir、Abeer Hashem、Elsayed Fathi Abd_Allah and Hanhong Bae著」等。
接下來,於下述實施例中詳細說明本發明化合物之製造方法、製劑方法以及用途,惟本發明並不受限於此等實施例。此外,作為本發明化合物的物性值之熔點,係使用柳本(Yanaco)製的MP-500V微量熔點測量裝置來進行測量。折射率係使用愛宕(Atago)製的阿貝折射計來進行測量。1
H 核磁共振(NMR, nuclear magnetic resonance)光譜係以四甲基矽烷(TMS)為內部標準並使用日本電子製的JNM-LA400(400MHz)、JNM-LA300(300MHz)或JNM-ECS300(300MHz)所測量而得。質量分析光譜係使用日本電子製的JMS-Q1500GC氣相色譜質量分析儀(電子衝擊(EI)法)所測量而得。
另外,也一併記載本發明化合物的製造中間體的製造方法。
[實施例1]
1-(2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-0145)之製造
1) 2-(乙硫基)苯胺
將2-氨基硫代苯酚(5.0g, 40mmol)及叔丁醇鉀(4.5g, 40mmol)溶解於乙醇(100mL)中。於冰冷下將碘乙烷(6.4g, 41mmol)滴加至此混合物中,且進一步於室溫下攪拌一整晚。過濾反應溶液,並於減壓下濃縮濾液。以二氯甲烷萃取殘渣,並依序以水及飽和食鹽水清洗有機層。以無水硫酸鎂來乾燥有機層之後,蒸餾出溶劑,獲得2-(乙硫基)苯胺(6.0g, 產率:98%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ(ppm)): 1.23(3H, t), 2.76(2H, q), 4.33(2H, br s), 6.66-6.74(2H, m), 7.09-7.14(1H, m), 7.37(1H, dd)
2) 1-(2-(乙硫基)苯基)-1H-吡唑-4-醇 (本發明化合物編號:E-0001)
將2-(乙硫基)苯胺(6.0g, 39mmol)溶解於濃鹽酸(13mL, 0.16mol)及水(26mL)中。於冰冷下,依序將亞硝酸鈉(3.5g, 51mmol)的水(6.5mL)溶液、4-氯乙醯乙酸(5.3g, 39mmol)的水(10mL)溶液以及乙酸鈉(6.4g, 78mmol)的水(16mL)溶液滴加至此混合物中,並進一步於室溫下攪拌1小時。將反應溶液注入水中,濾取析出的固體,並使其乾燥,獲得粗製的1-(3-氯-2-氧代亞丙基)-2-(2-(乙硫基)苯基) 肼。將獲得的粗製的1-(3-氯-2-氧代亞丙基)-2-(2-(乙硫基)苯基) 肼溶解於甲醇(80mL)中,並加入氫氧化鈉(3.9g, 98mmol),於室溫下攪拌1小時。於減壓下蒸餾出溶劑,並加入濃鹽酸直到pH達到1。用乙酸乙酯萃取殘渣,並用無水硫酸鎂使其乾燥之後蒸餾出溶劑。以矽膠柱色譜法純化殘渣,並獲得1-(2-(乙硫基)苯基)-1H-吡唑-4-醇(5.4g, 產率:63%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.23(3H, t), 2.78(2H, q), 5.93(1H, br s), 7.21-7.45(6H, m)
3)1-(2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-0145)
依序將1-(2-(乙硫基)苯基)-1H-吡唑-4-醇(2.0g, 9.1mmol)、碳酸鉀(2.5g, 18mmol)以及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(5.3g, 11mmol)加入至二甲基甲醯胺(DMF, dimethylformamide)(18mL)中,並進一步於室溫下攪拌4小時。將反應溶液注入水中,並用二異丙醚進行萃取。用無水流酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。以矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(3.6g, 產率:99%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.25(3H, t), 2.80(2H, q), 4.42(2H, tt), 7.26-7.43 (4H, m), 7.55(1H, s), 7.60(1H, s)
折射率 n20 D
1.4855
[實施例2]
1-(2-(乙基亞硫醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-0146)以及1- (2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-0147)之製造
於冰冷下,依序將1-(2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.40g, 0.99mmol)及間氯過苯甲酸(含量:77%, 0.31g, 1.4mmol)加入至氯仿(10mL)中,並進一步於冰冷下攪拌1小時。將反應溶液注入飽和碳酸氫鈉水溶液中,並用氯仿進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙基亞磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.21g, 產率:50%)及1-(2-(乙基亞磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.17g, 產率:39%)。
1-(2-(乙基亞磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.30(3H, t), 2.73(1H, dq), 3.20(1H, dq), 4.44(2H, tt), 7.36-8.19(6H, m)
折射率 n20 D
1.4956
1-(2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.21(3H, t), 3.16(2H, q), 4.42(2H, tt), 7.47(1H, dd), 7.57(1H, dd), 7.65(1H, dd), 7.66(1H, ddd), 7.75(1H, ddd), 8.19(1H, dd)
熔點 111-114℃
[實施例3]
1-(4-(芐氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2506)之製造
1) 4-(芐氧基)-2-(乙硫基)-1-硝基苯
依序將3-氟-4-硝基苯酚(5.2g, 33mmol)、碳酸鉀(5.5g, 40mmol)及芐基溴(5.6g, 33mmol)加入至DMF(33mL)中,並進一步於室溫下攪拌2小時。依序將碳酸鉀(5.5g, 40mmol)及乙醇硫(3.0mL, 40mmol)加入至反應溶液中,並進一步於80℃下攪拌3小時。將反應溶液注入至水中,濾取析出的固體,依序用水及己烷清洗之後,使其乾燥,獲得4-(芐氧基)-2-(乙硫基)-1-硝基苯(8.4g, 產率:88%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.37(3H, t), 2.89(2H, q), 5.17(2H, s), 6.78(1H, dd), 6.86(1H, d), 7.34-7.43(5H, m), 8.27(1H, d)
2) 4-(芐氧基)-2-(乙硫基)苯胺
依序將4-(芐氧基)-2-(乙硫基)-1-硝基苯(8.1g, 28mmol)及鐵粉(4.7g, 84mmol)加入至乙酸(28mL)與乙醇(28mL)的混合溶劑中,且進一步於加熱回流下攪拌4小時。將濃鹽酸(0.23mL, 2.8mmol)加入至反應溶液中,且進一步於加熱回流下攪拌3小時。濃縮反應溶液,並用飽和碳酸氫鈉水溶液進行中和。將乙酸乙酯加入至殘渣中,並透過矽藻土過濾之後,依序用飽和碳酸氫鈉水溶液及飽和食鹽水清洗有機層。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得4-(芐氧基)-2-(乙硫基)苯胺(6.8g, 產率:94%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.21(3H, t), 2.77(2H, q), 4.22(2H, br s), 4.99(2H, s), 6.68(1H, d), 6.80(1H, dd), 7.03(1H, d), 7.28-7.44(5H, m)
3) 1-(4-(芐氧基)-2-(乙硫基)苯基)-1H-吡唑-4-醇(本發明化合物編號:D-0302)
使4-(芐氧基)-2-(乙硫基) 苯胺(6.8g, 26mmol)懸浮於濃鹽酸(9mL, 0.11mol)及水(52mL)中。於冰冷下,依序將亞硝酸鈉(2.3g, 33mmol)的水(26mL)溶液、4-氯乙醯乙酸(3.6g, 26mmol)及乙酸鈉(4.3g, 52mmol)的水(26mL)溶液滴加至此混合物中,並進一步於室溫下攪拌3小時。將反應溶液注入水中,濾取析出的固體,使其乾燥,獲得粗製的1-(3-氯-2-氧代丙烯基)-2-(4-(芐氧基)-2-(乙硫基)苯基)肼。將獲得的粗製的1-(3-氯-2-氧代丙烯基)-2-(4-(芐氧基)-2-(乙硫基)苯基)肼溶解於甲醇(100mL)中,並加入氫氧化鈉(2.1g, 53mmol),於室溫下攪拌一整晚。於減壓下蒸餾出溶劑,加入濃鹽酸直到pH達到3。用乙酸乙酯萃取殘渣,並用無水硫酸鎂使其乾燥之後,蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(4-(芐氧基)-2-(乙硫基)苯基)-1H-吡唑-4-醇(2.5g, 產率:29%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.22(3H, t), 2.76(2H, q), 4.37(1H, br s), 5.10(2H, s), 6.81(1H, dd), 6.95(1H, d), 7.25(1H, d), 7.34-7.46(7H, m)
4)1-(4-(芐氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2506)
依序將1-(4-(芐氧基)-2-(乙硫基)苯基)-1H-吡唑-4-醇(1.5g, 4.6mmol)、碳酸鉀(1.0g, 7.2mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(2.5g, 5.2mmol)加入至DMF(10mL)中,並進一步於室溫下攪拌一整晚。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(4-(芐氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(2.0g, 產率:86%)。
1
H-NMR數據(300MHz,CDCl3
/TMS δ (ppm)):1.23(3H, t), 2.76(2H, q), 4.41(2H, tt), 5.11(2H, s), 6.81-6.97(2H, m), 7.25-7.52(8H, m)
[實施例4]
1-(2-(乙硫基)-4-羥基苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2239)之製造
將1-(4-(芐氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.9g, 3.7mmol)溶解於二氯甲烷(20mL)中。於冰冷下,將三溴化硼二氯甲烷溶液(1mol/L, 4.1mL, 4.1mmol)加入至此混合物中,並且進一步於冰冷下攪拌1小時。將反應溶液注入濃鹽酸中,並且用二氯甲烷進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)-4-羥基苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.2g, 產率:77%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.25(3H, t), 2.77(2H, q), 4.41(2H, tt), 6.55-6.58 (2H, m), 6.77(1H, d), 7.12(1H, d), 7.45(1H, s), 7.53(1H, s)
折射率 n20 D
1.5018
[實施例5]
1-(4-(二氟甲氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2269)之製造
依序將1-(2-(乙硫基)-4-羥基苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.40g, 0.96mmol)及碳酸鉀(0.20g, 1.4mmol)加入至DMF(10mL)中,並於氯二氟甲烷氣氛下於60℃攪拌5小時。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(4-(二氟甲氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.19g, 產率:42%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 2.84(2H, q), 4.42(2H, tt), 6.55(1H, t), 7.00(1H, dd), 7.13(1H, d), 7.36(1H, d), 7.55(2H, s)
折射率 n20 D
1.4774
[實施例6]
1-(4-(二氟甲氧基)-2-(乙基亞硫醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2270)之製造
於冰冷下,依序將1-(4-(二氟甲氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.15g, 0.32mmol)及間氯過苯甲酸(含量:77%, 0.075g, 0.33mmol)加入至氯仿(10mL)中,並進一步於冰冷下攪拌1小時。將反應溶液注入飽和碳酸氫鉀水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得1-(4-(二氟甲氧基)-2-(乙基亞硫醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.15g, 產率:97%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 2.72(1H, dq), 3.20(1H, dq), 4.43(2H, tt), 6.63(1H, t), 7.31(1H, dd), 7.40(1H, d), 7.55(1H, dd), 7.60(1H, dd), 7.90 (1H, d)
[實施例7]
1-(4-(二氟甲氧基)-2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2271)之製造
於室溫下依序將1-(4-(二氟甲氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.10g, 0.21mmol)及間氯過苯甲酸(含量:77%, 0.12g, 0.54mmol)加入至氯仿(1mL)中,並進一步攪拌一整晚。將反應溶液注入至飽和碳酸氫鈉水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(4-(二氟甲氧基)-2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.090g, 產率:84%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.23(3H, t), 3.15(2H, q), 4.42(2H, tt), 6.64(1H, t), 7.46-7.52(2H, m), 7.57(1H, d), 7.62(1H, d), 7.93(1H, d)
熔點 65-68℃
[實施例8]
1-(4-(2-氯-1,1,2-三氟乙氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2296)之製造
將1-(2-(乙硫基)-4-羥基苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.0g, 2.4mmol)及碳酸鉀(0.50g, 3.6mmol)加入至DMF(12mL)中,並於三氟氯乙烯氣氛下於室溫下攪拌3小時。將反應溶液注入至水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後蒸餾出溶劑,獲得1-(4-(2-氯-1,1,2-三氟乙氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.2g, 產率:94%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 2.85(2H, q), 4.42(2H, tt), 6.29(1H, dt), 7.09-7.13(1H, m), 7.21(1H, d), 7.38(1H, d), 7.56(1H, d), 7.57(1H, d)
熔點 37-40℃
[實施例9]
1-(4-(2-氯-1,1,2-三氟乙氧基)-2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2298)之製造
於室溫下依序將1-(4-(2-氯-1,1,2-三氟乙氧基)-2-(乙硫基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.0g, 1.9mmol)及間氯過苯甲酸(含量:77%, 0.92g, 4.1mmol)加入至二氯甲烷(9mL)中,並進一步攪拌一整晚。將反應溶液注入至碳酸鉀水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得1-(4-(2-氯-1,1,2-三氟乙氧基)-2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.0g, 產率:94%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.23(3H, t), 3.18(2H, q), 4.42(2H, tt), 6.32(1H, dt), 7.51(1H, d), 7.58(1H, d), 7.59-7.62(1H, m), 7.64(1H, d), 8.04(1H, d)
熔點 44-47℃
[實施例10]
1-(2-(乙基亞磺醯基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2453)以及1-(2-(乙基磺醯基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2454)之製造
1) 1-(2-(乙硫基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2452)
依序將1-(2-(乙硫基)-4-羥基苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.50g, 1.2mmol)、碳酸鉀(0.20g, 1.4mmol)及1-溴-5-(三氟甲硫基) 戊烷(含量:85%, 0.43g, 1.5mmol)加入至乙腈(6mL)中,並進一步於加熱回流下攪拌4小時。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.64g, 產率:91%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.26(3H, t), 1.56-1.67(2H, m), 1.75-1.89(4H, m), 2.79(2H, q), 2.93(2H, t), 4.00(2H, t), 4.41(2H, tt), 6.74(1H, dd), 6.89(1H, d), 7.26(1H, d), 7.49(1H, d), 7.51(1H, d)
熔點 0-30℃
2) 1-(2-(乙基亞磺醯基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2453)及1-(2-(乙基磺醯基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2454)
將1-(2-(乙硫基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.50g, 0.85mmol)溶解於二氯甲烷(4mL)中。於冰冷下,將間氯過苯甲酸(含量:77%, 0.30g, 1.3mmol)加入至此混合物中,並且進一步於室溫下攪拌一整晚。將反應溶液注入至碳酸鉀水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙基亞磺醯基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.27g, 產率:53%)及1-(2-(乙基磺醯基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.21g, 產率:40%)。
1-(2-(乙基亞磺醯基)-4-(5-(三氟甲硫基)戊氧基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ(ppm)):1.26(3H, t), 1.56-1.67(2H, m), 1.75-1.91(4H, m), 2.64(1H, dq), 2.93(2H, t), 3.10(1H, dq), 4.04-4.15(2H, m), 4.42(2H, tt), 7.03(1H, dd), 7.30(1H, d), 7.50(1H, d), 7.51(1H, d), 7.60(1H, d)
熔點 58-61℃
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.20(3H, t), 1.60-1.68(2H, m), 1.76-1.92(4H, m), 2.93(2H, t), 3.06(2H, q), 4.08(2H, t), 4.40(2H, tt), 7.17(1H, dd), 7.36(1H, d), 7.53(1H, d), 7.56(1H, d), 7.63(1H, d)
熔點 55-57℃
[實施例11]
1-(2-(乙硫基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:K-0071)之製造
1)1-(2-(乙硫基)苯基)-1H-吡唑-3-醇(本發明化合物編號:K-0002)
將2-(乙硫基) 苯胺(9.4g, 61mmol)溶解於濃鹽酸(60mL)中。於冰冷下,依序將亞硝酸鈉(4.4g, 64mmol)的水(30mL)溶液及SnCl2
(23g, 121mmol)的濃鹽酸(30mL)溶液滴加至此混合物中,並進一步於冰冷下攪拌1小時。濾取析出的固體,用濃鹽酸清洗之後,使其風乾,獲得粗製的(2-(乙硫基)苯基)肼鹽酸鹽。將所獲得的粗製的(2-(乙硫基)苯基)肼鹽酸鹽(1.0g, 4.9mmol)及碳酸鉀(4.2g, 30mmol)溶解於四氫呋喃(THF, tetrahydrofuran)(20mL)及水(10mL)中。將3-溴丙醯氯(0.86g, 5.0mmol)滴加至此混合物中,並進一步於室溫下攪拌一整晚。濃縮反應溶液,加入飽和氯化銨水溶液之後,用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得粗製的1-(2-(乙硫基)苯基)吡唑烷-3-酮。將所獲得的粗製的1-(2-(乙硫基)苯基)吡唑烷-3-酮溶解於甲苯(40mL)及水(40mL)中。依序將過錳酸鉀(0.25g, 1.6mmol)及溴化四丁基銨(0.050g, 16mmol)加入至此混合物中,並且進一步於室溫下攪拌10分鐘。用矽藻土過濾反應溶液,於減壓下蒸餾出甲苯。用乙酸乙酯萃取殘渣,並用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)苯基)-1H-吡唑-3-醇(0.28g, 產率:26%)。
1
H-NMR數據(400MHz, CDCl3
/TMS δ (ppm)):1.22(3H, t), 2.79(2H, q), 5.82(1H, d), 7.27-7.44 (5H, m), 7.58(1H, d)
熔點 135-138℃
2)1-(2-(乙硫基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:K-0071)
依序將1-(2-(乙硫基)苯基)-1H-吡唑-3-醇(0.66g, 3.0mmol)及碳酸鉀(1.1g, 8.0mmol)加入至DMF(18mL)中,於冰冷下,滴加九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(2.0g, 4.1mmol),並進一步於室溫下攪拌一整晚。將反應溶液注入稀鹽酸中,用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.0g, 產率:83%)。
1
H-NMR數據(400MHz, CDCl3
/TMS δ (ppm)):1.24(3H, t), 2.81(2H, q), 4.76(2H, tt), 5.96(1H, d), 7.23-7.43(4H, m), 7.63(1H, d)
折射率 n20 D
1.4879
[實施例12]
1-(2-(乙基亞磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:K-0072)及1-(2-(乙基磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:K-0073)之製造
於冰冷下,依序將1-(2-(乙硫基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.75g, 1.9mmol)及間氯過苯甲酸(含量:77%, 0.67g, 3.0mmol)加入氯仿(10mL)中,並進一步於室溫下攪拌一整晚。將反應溶液注入飽和碳酸氫鈉水溶液中,並用氯仿進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓之下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙基亞磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.31g, 產率:40%)及(2-(乙磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.34g, 產率:42%)。
1-(2-(乙基亞磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.23(3H, t), 2.64(1H, dq), 3.06(1H, dq), 4.72(2H, tt), 6.02(1H, d), 7.36-8.15(5H, m)
折射率 n20 D
1.4968
1-(2-(乙基磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.19(3H, t), 3.03(2H, q), 4.70(2H, tt), 5.99(1H, d), 7.45-8.19(5H, m)
折射率 n20 D
1.4769
[實施例13]
4-乙氧基-1-(2-(乙硫基)-4-(三氟甲基)苯基)-1H-1,2,3-三唑(本發明化合編號:K-1042)之製造
1)2-(乙硫基)-4-(三氟甲基)苯胺
將2-氨基-6-(三氟甲基)苯並噻唑(20.0g, 0.0917mol)溶解於THF(92mL)中。於加熱回流下,將亞硝酸叔丁酯(含量:90%, 15.8g, 0.138mol)滴加至此混合物中,並且進一步於加熱回流下攪拌1小時。濃縮反應溶液,將殘渣溶解於乙醇(92mL)中。將肼一水合物(23.0g, 0.459mol)加入至此混合物中,並進一步於加熱回流下攪拌1.5小時。將反應溶液用冰冷卻,並依序加入叔丁醇鉀(10.8g, 0.0963mol)及碘乙烷(15.0g, 0.0962mol),並進一步於冰冷下攪拌1小時。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得2-(乙硫基)-4-(三氟甲基)苯胺(9.3g, 產率:46%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.24(3H, t), 2.78(2H, q), 4.66(2H, br s), 6.74(1H, d), 7.33(1H, dd), 7.62(1H, d)
2)1-疊氮基-2-(乙硫基)-4-(三氟甲基)苯
將2-(乙硫基)-4-(三氟甲基)苯胺(2.0g, 9.0mmol)及三甲基疊氮矽烷(1.2g, 10mmol)溶解於乙腈(18mL)中。於冰冷下將亞硝酸叔丁酯(含量:90%, 1.0g, 8.7mmol)滴加至此混合物中,並進一步於室溫下攪拌1小時。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得1-疊氮基-2-(乙硫基)-4-(三氟甲基)苯(1.2g, 產率:54%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.35(3H, t), 2.98(2H, q), 7.18-7.22(1H, m), 7.44-7.47(2H, m)
3)4-乙氧基-1-(2-(乙硫基)-4-(三氟甲基)苯基)-1H-1,2,3-三唑(本發明化合物編號:K-1042)
依序將1-疊氮基-2-(乙硫基)-4-(三氟甲基)苯(1.1g, 4.4mmol)、乙炔(含量:40%, 1.6g, 9.1mmol)、五水合硫酸銅(0.11g, 0.44mmol)及抗壞血酸鈉(0.44g, 2.2mmol)加入至乙醇(22mL)中,並進一步於室溫下攪拌一整晚。濃縮反應溶液,用矽膠柱色譜法純化,獲得4-乙氧基-1-(2-(乙硫基)-4-(三氟甲基)苯基)-1H-1,2,3-三唑(1.1g, 產率:78%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 1.47(3H, t), 2.89(2H, q), 4.39(2H, q), 7.45(1H, s), 7.56(1H, dd), 7.60(1H, d), 7.68(1H, d)
熔點 61-63℃
[實施例14]
3-(2,2,3,3,4,4,4-七氟丁氧基)-1-(2-(甲硫基)苯基)-1H-1,2,4-三唑(本發明化合物編號:K-1505)之製造
依序將(2-(甲硫基)苯基)肼鹽酸鹽(28.1g, 147mmol)及氰酸鈉(14.3g, 220mmol)加入至水(735mL)中,並且進一步於加熱回流下攪拌1小時。濾取析出的結晶,並用水清洗。於減壓下進行加熱乾燥,獲得2-(2-(甲硫基)苯基)肼-1-羧醯胺(16.3g, 產率:56%)。
依序將所獲得的2-(2-(甲硫基)苯基)肼-1-羧醯胺(16g, 81mmol)及甲烷磺酸(0.78g, 8.1mmol)加入至原甲酸三甲酯(162mL)中,並進一步於加熱回流下攪拌12小時。濃縮反應溶液,用二異丙醚清洗殘渣,獲得1-(2-(甲硫基)苯基)-1H-1,2,4-三唑-3-醇(9.7g, 產率:58%)。
依序將所獲得的1-(2-(甲硫基)苯基)-1H-1,2,4-三唑-3-醇(6.3g, 30mmol)、碳酸鉀(4.6g, 33mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(15g, 31mmol)加入至二甲基亞碸(DMSO, Dimethyl sulfoxide) (150mL)中,並於室溫下攪拌一整晚。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(2,2,3,3,4,4,4-七氟丁氧基)-1-(2-(甲硫基)苯基)-1H-1,2,4-三唑(11g, 產率:93%)。
1
H-NMR數據(400MHz, CDCl3
/TMS δ (ppm)):2.43(3H, s), 4.86(2H, t), 7.19-7.47(4H, m), 8.11(1H, s)
折射率 n20 D
1.4921
[實施例15]
3-(2,2,3,3,4,4,4-七氟丁氧基)-1-(2-(甲基亞磺醯基)苯基)-1H-1,2,4-三唑(本發明化合物編號:K-1506)之製造
將3-(2,2,3,3,4,4,4-七氟丁氧基)-1-(2-(甲硫基)苯基)-1H-1,2,4-三唑(8.1 g, 21 mmol)溶解於氯仿(150mL)中。於室溫下於15分鐘內逐次少量地將間氯過苯甲酸(含量:77%, 4.7g, 21mmol)加入此混合物中,並且進一步攪拌1小時。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得3-(2,2,3,3,4,4,4-七氟丁氧基)-1-(2-(甲基亞磺醯基)苯基)-1H-1,2,4-三唑(7.3g, 產率:87%)。
1
H-NMR數據(400MHz, CDCl3
/TMS δ (ppm)):2.90(3H, s), 4.86(2H, t), 7.45-8.29(5H, m)
折射率 n20 D
1.4976
[實施例16]
1-(2-(乙基亞磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑(本發明化合物編號:K-1419)及1-(2-(乙磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑(本發明化合物編號:K-1420)之製造
於室溫下依序將以與實施例14相同的方式合成的1-(2-(乙硫基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑(1.9g, 4.7mmol)及間氯過苯甲酸(含量:77%, 2.4g, 11mmol)加入至氯仿(50mL)中,並且進一步攪拌一整晚。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得1-(2-(乙基亞磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑(0.78g, 產率:39%)及1-(2-(乙磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑(0.95g, 產率:46%)。
1-(2-(乙基亞磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑
1
H-NMR數據(400MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 2.87(1H, dq), 3.17(1H, dq), 4.86(2H, t), 7.45-8.20(5H, m)
熔點 80-83℃
1-(2-(乙基磺醯基)苯基)-3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑
1
H-NMR數據(400MHz, CDCl3
/TMS δ (ppm)):1.22(3H, t), 3.17(2H, q), 4.88(2H, t), 7.54-8.23 (5H, m)
熔點 66-69℃
[實施例17]
2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙硫基)吡啶(本發明化合物編號:F-0239)之製造
1)4-碘-1-(甲氧基甲基)-1H-吡唑
將4-碘-1H-吡唑(10.0g, 51.5mmol)及N,N-二異丙基乙胺(10.8mL, 61.9mmol)溶解於二氯甲烷(50mL)中。於冰冷下將氯甲基甲醚(4.3mL, 56.6mmol)滴加至此混合物中,並進一步於室溫下攪拌一整晚。將反應溶液注入水中,並用二氯甲烷進行萃取。用水及飽和食鹽水清洗有機層,用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得4-碘-1-(甲氧基甲基)-1H-吡唑(12.9g, 產率:定量(98%以上))。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):3.33(3H, s), 5.38(2H, s), 7.57(1H, s), 7.63(1H, s)
2)4-(芐氧基)-1-(甲氧基甲基)-1H-吡唑
依序將4-碘-1-(甲氧基甲基)-1H-吡唑(5.0g, 21mmol)、芐醇(4.5g, 42mmol)、碳酸銫(14g, 43mmol)、碘化銅(0.20g, 1.0mmol)及3,4,7,8-四甲基-1,10-菲咯啉(0.50g, 2.1mmol)加入至甲苯(40mL)中,且進一步在加熱回流下攪拌10小時。將二異丙醚加入至反應溶液中,並透過矽藻土過濾。於減壓下蒸餾出溶劑,並用矽膠柱色譜法純化殘渣,獲得4-(芐氧基)-1-(甲氧基甲基)-1H-吡唑(3.2g, 產率:70%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):3.28(3H, s), 4.95(2H, s), 5.27(2H, s), 7.23(1H, d), 7.30-7.43(6H, m)
3)4-(芐氧基)-1H-吡唑
依序加入4-(芐氧基)-1-(甲氧基甲基)-1H-吡唑(3.2g, 15mmol)及濃鹽酸(12mL, 0.14 mol)加入至甲醇(30mL)中,並進一步於加熱回流下攪拌4小時。將反應溶液注入至10%碳酸鉀水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得4-(芐氧基)-1H-吡唑(1.1g, 產率:43%)。
1
H-NMR數據(300 MHz, CDCl3
/TMS δ (ppm)):4.96(2H, s), 7.30-7.44(7H, m)
4)3-(乙硫基)-2-氟吡啶
將二異丙基氨基鋰(2 mol/L,THF/庚烷/乙苯溶液,100 mL,0.200 mol)冷卻至-78℃,加入2-氟吡啶(17.7g, 0.182 mol),並進一步於-78℃下攪拌30分鐘。將二乙基二硫醚(23.4g, 0.191 mol)加入至反應溶液中,並進一步於-78℃下攪拌2小時。將反應溶液升溫至-30℃,並進一步於-30℃下攪拌30分鐘。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後蒸餾出溶劑,獲得粗製的3-(乙硫基)-2-氟吡啶(35.5g, 純度:60%, 產率:74%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.33(3H, t), 2.97(2H, q), 7.14(1H, ddd), 7.71(1H, ddd), 8.03(1H, ddd)
5)2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙硫基)吡啶(本發明化合物編號:F-0239)
依序將粗製的3-(乙硫基)-2-氟吡啶(純度:60%, 5.0g, 19mmol)、4-(芐氧基)-1H-吡唑(3.3g, 19mmol)及碳酸鉀(3.2g, 23mmol)加入至DMF(19mL)中,並進一步於120℃下攪拌2小時,接著於140℃下攪拌4小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙硫基)吡啶(3.5g, 產率:59%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.35(3H, t), 2.91(2H, q), 5.03(2H, s), 7.17(1H, dd), 7.31-7.46(5H, m), 7.61(1H, d), 7.69(1H, dd), 8.01(1H, d), 8.19(1H, dd)
折射率 n20 D
1.6397
[實施例18]
1-(2-(乙硫基)苯基)-3,5-二甲基-1H-吡唑-4-醇(本發明化合物編號:D-1094)之製造
1)對甲苯甲酸2,4-二氧戊烷-3-基
依序將3-氯乙醯丙酮(25.0g, 0.186 mol)、對甲苯甲酸(25.3g, 0.186 mol)及經粉碎的氫氧化鉀(含量:85.0%, 12.3g, 0.186 mol)加入至DMF(90mL)中,並進一步於室溫下攪拌一整晚。用乙酸乙酯將反應溶液稀釋,用水清洗有機層。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得對甲基苯甲酸2,4-二氧戊烷-3-基(37.3g, 產率:86%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):酮型(keto-form) 2.39(6H, s), 2.45(3H, s), 5.71(1H, s), 7.28- 7.31(2H, m), 7.99-8.03(2H, m);烯醇型(enol-form) 2.05-2.06(6H, m), 2.46(3H, s), 7.31-7.34(2H, m), 8.04-8.08(2H, m)
2)1-(2-(乙硫基)苯基)-3,5-二甲基-1H-吡唑-4-醇(本發明化合物編號:D-1094)
依序將(2-(乙硫基)苯基)肼(2.0g, 12mmol)及對甲苯甲酸2,4-二氧戊丹-3-基(2.8g, 12mmol)加入至乙醇(20 mL)中,並進一步於加熱回流下攪拌3小時。於減壓下濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得粗製的對甲苯甲酸1-(2-(乙硫基)苯基)-3,5-二甲基-1H-吡唑-4-基。將所獲得的粗製的對甲苯甲酸1-(2-(乙硫基)苯基)-3,5-二甲基-1H-吡唑-4-基溶解於THF(5mL)中,並加入氫氧化鈉(0.30g, 7.5mmol)的水(5mL)溶液,於80℃下攪拌3小時。將反應溶液注入至飽和食鹽水中,用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)苯基)-3,5-二甲基-1H-吡唑-4-醇(0.76g, 產率:26%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.26(3H, t), 2.04(3H, s), 2.27(3H, s), 2.84(2H, q), 7.21-7.23(2H, m), 7.33-7.40(2H, m)
[實施例19]
1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-羧酸乙酯(本發明化合物編號:A-3406)之製造
1)1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-羥基-1H-吡唑-3-羧酸乙酯(本發明化合物編號:D-0629)
將2-(乙硫基)-4-(三氯甲基)苯胺(4.0g,18mmol)溶解於乙酸(18mL)與水(9mL)的混合溶劑中。於冰冷下,依序將亞硝酸鈉(1.3g, 19mmol)的水(9mL)溶液及4-氯乙醯乙酸乙酯(3.0g, 18mmol)加入至此混合物中,並進一步於室溫下攪拌1小時。將反應溶液注入水中,濾取析出的固體,使其乾燥,獲得粗製的4-氯-2-(2-(2-(乙硫基)-4-(三氟甲基)苯基)肼基)-3-氧代丁酸酯。將所獲得的粗製的4-氯-2-(2-(2-(乙硫基)-4-(三氟甲基)苯基)肼基)-3-氧代丁酸酯懸浮於乙醇(36mL)中,於冰冷下,加入叔丁醇鉀(2.5g, 22mmol),並進一步於室溫下攪拌1小時。於減壓下蒸餾出溶劑,將稀鹽酸加入殘渣中,用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-羥基-1H-吡唑-3-羧酸乙酯(3.9g, 產率:60%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.28(3H, t), 1.45(3H, t), 2.88(2H, q), 4.49(2H, q), 7.35(1H, s), 7.51(1H, dd), 7.56(1H, s), 7.57(1H, d), 7.62(1H, d)
熔點 65-66℃
2)1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-羧酸乙基酸(本發明化合物編號:A-3406)
依序將1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-羥基-1H-吡唑-3-羧酸乙酯(2.0g, 5.5mmol)、碳酸鉀(1.9g, 14mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(4.8g, 10mmol)加入至乙腈(28mL)中,並進一步於加熱回流下攪拌1小時。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-羧酸乙酯(2.5g, 產率:83%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.28(3H, t), 1.42(3H, t), 2.87(2H, q), 4.45(2H, q), 4.58(2H, tt), 7.53(1H, dd), 7.61(1H, d), 7.64(1H, d), 7.75(1H, s)
折射率 n20 D
1.4827
[實施例20]
3-氯-1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-3186)之製造
1)1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-羧酸(本發明化合物編號:A-3388)
依序將1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-羧酸乙酯(2.0g, 3.7mmol)、氫氧化鉀(含量:85%, 0.37g, 5.6mmol)及四丁基溴化銨(0.12g, 0.37mmol)加入至THF(4mL)與水(12mL)的混合溶劑中,並進一步於80℃下攪拌2小時。於減壓下蒸餾出溶劑,並加入濃鹽酸直到pH達到1。用乙酸乙酯萃取殘渣,用無水硫酸鎂使其乾燥之後,蒸餾出溶劑,獲得1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-羧酸(1.9g, 產率:定量)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 2.90(2H, q), 4.64(2H, tt), 7.55(1H, dd), 7.60(1H, d), 7.66(1H, d), 7.78(1H, s)
折射率 n20 D
1.4947
2)(1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3- 基)氨基甲酸叔丁酯(本發明化合物編號:A-3370)
依序將1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-羧酸(1.8g, 3.5mmol)、二苯基磷醯基疊氮化物(1.1g, 4.0mmol)及三乙胺(0.43g, 4.2mmol)加入至叔丁醇(7mL)中,並進一步於加熱回流下攪拌3小時。於減壓下蒸餾出溶劑,將殘渣溶解於乙酸乙酯中。依序用檸檬酸水溶液、碳酸鉀水溶液、飽和食鹽水來清洗有機層。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得(1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-基)氨基甲酸叔丁酯(2.0g, 產率:98%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.28(3H, dt), 1.52(9H, s), 2.89(2H, dq), 4.44-4.53 (2H, m), 7.49(1H, d), 7.56(1H, d), 7.61(1H, s), 7.75(1H, s)
折射率 n20 D
1.4940
3)3-氨基-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-3352)
將(1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-3-基)氨基甲酸叔丁酯(1.9g, 3.2mmol)溶解於三氟乙酸(9.6mL)中,並進一步於室溫下攪拌1小時。於減壓下蒸餾出溶劑之後,將碳酸鉀水溶液加入殘渣中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得3-氨基-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.6g, 產率:定量)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 2.89(2H, dq), 4.36-4.53(2H, m), 7.37-7.74(4H, m)
折射率 n20 D
1.5062
4)3-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-3184)
依序將3-氨基-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.5g, 3.1mmol)、氯化銅(II)(0.52g, 3.9mmol)及亞硝酸叔丁酯(含量:90%, 0.45g, 3.9mmol)加入至乙腈(16mL)中,並進一步於加熱回流下攪拌2小時。將亞硝酸叔丁酯(含量:90%, 0.45g, 3.9mmol)加入至反應溶液中,並進一步於加熱回流下攪拌2小時。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得3-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.15g, 產率:10%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 2.89(2H, q), 4.49(2H, tt), 7.51(1H, dd), 7.55(1H, d), 7.63(1H, d), 7.74(1H, s)
5)3-氯-1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-3186)
依序將3-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.15g, 0.30mmol)及間氯過苯甲酸(含量:77%, 0.17g, 0.76mmol)於室溫下加入至二氯甲烷(3mL)中,並進一步攪拌一整晚。將反應溶液注入飽和碳酸氫鈉水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得3-氯-1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.18g, 產率:定量)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.28(3H, t), 3.29(2H, q), 4.48(2H, tt), 7.63(1H, d), 7.71(1H, s), 8.01(1H, dd), 8.46(1H, d)。
熔點 111-113℃
[實施例21]
5-氯-1-(2-(乙基亞磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(本發明化合物編號:A-3887)及5-氯-1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(本發明化合物編號:A-3888)之製造
1)4,4-二氯乙酸甲酯
將米氏酸(meldrum酸)(7.5g, 52mmol)及吡啶(7.5g, 95mmol)溶解於二氯甲烷(50mL)中。於冰冷下,將二氯乙醯氯(7.0g, 47mmol)滴加至此混合物中,並進一步於室溫下攪拌一整晚。將反應溶液注入冰水中,並用二氯甲烷進行萃取。以經冰冷過的稀鹽酸清洗有機層,用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得粗製的(2,2-二氯-1-羥基亞乙基)丙二酸異亞丙基酯。將所獲得的粗製的(2,2-二氯-1-羥基亞乙基)丙二酸異亞丙基酯溶解於甲醇(30mL)中,並於加熱回流下攪拌2小時。濃縮反應溶液之後,透過二氧化矽凝膠的短墊過濾,並用己烷/二異丙醚(1:1)的混合溶劑進行溶析。蒸餾出溶劑,獲得4,4-二氯乙酸乙酸甲酯(7.0g, 產率:80%)。
1
H-NMR數據(300 MHz, CDCl3
/TMS δ (ppm)):3.78(3H, s), 3.88(2H, s), 6.03(1H, s)
2)4,4-二氯乙醯乙酸
將4,4-二氯乙酸乙酸甲酯(6.9g, 37mmol)溶解於濃鹽酸(30mL)與水(10mL)的混合溶劑中,並進一步於室溫下攪拌一整晚。將反應溶液注入冰水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,並將殘渣溶解於飽和碳酸氫鈉水溶液中。用二異丙醚來清洗所獲得的水溶液,將濃鹽酸加入水層使其呈酸性之後,用乙酸乙酯萃取水層。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得4,4-二氯乙醯乙酸(4.5g, 產率:71%)。
1
H-NMR數據(300 MHz, CDCl3
/TMS δ (ppm)):3.94(2H, s), 6.02(1H, s)
3)5-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-1H-吡唑-4-醇(本發明化合物編號:D-0644)
將2-(乙硫基)-4-(三氟甲基)苯胺(2.5g, 11mmol)溶解於濃鹽酸(5mL, 0.06mol)及水(15mL)中。於冰冷下,依序將亞硝酸鈉(0.86g, 12mmol)的水(10mL)溶液、4,4-二氯乙醯乙酸(2.2g, 13mmol)的水(10mL)懸浮液及乙酸鈉(1.9, 23mmol)的水(20mL)溶液滴加至此混合物,並進一步於室溫下攪拌3小時。將反應溶液注入水中,濾取析出的固體。將所濾取的固體溶解於乙酸乙酯中,並用飽和食鹽水清洗有機層。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得粗製的1-(3,3-二氯-2-氧代亞丙基)-2-(2-(乙硫基)-4-(三氟甲基)苯基)肼。將所獲得的粗製的1-(3,3-二氯-2-氧代亞丙基)-2-(2-(乙硫基)-4-(三氟甲基)苯基)肼溶解於DMF(55mL)中,加入碳酸鉀(3.2g, 23mmol),並進一步於50℃下攪拌2小時。將反應溶液注入檸檬酸水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得5-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-1H-吡唑-4-醇(0.45g, 產率:12%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.30(3H, t), 2.92(2H, q), 4.49(1H, br s), 7.39(1H, d), 7.50-7.53(1H, m), 7.56(1H, s), 7.61-7.62(1H, m)
4)5-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(本發明化合物編號:A-3886)
依序將5-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-1H-吡唑-4-醇(0.45g, 1.4mmol)、碳酸鉀(0.39g, 2.8mmol)及九氟丁烷磺酸2,2,3,4,4,4-六氟丁基(0.71g, 1.5mmol)加入至DMF(5.6mL)中,並於室溫下進一步攪拌4小時。將反應溶液注入至檸檬酸水溶液中,並用己烷/乙酸乙酯(1:1)的混合溶劑進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得5-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(0.23g, 產率:34%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.30(3H, t), 2.94(2H, q), 4.29-4.54(2H, m), 5.07-5.34(1H, m), 7.41(1H, d), 7.54(1H, d), 7.63(2H, br s)
折射率 n20 D
1.4786
5)5-氯-1-(2-(乙基亞磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(本發明化合物編號:A-3887)及5-氯-1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(本發明化合物編號:A-3888)
於室溫下依序將5-氯-1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(0.37g, 0.76mmol)及間氯過苯甲酸(含量:77%, 0.27g, 1.2mmol)加入至氯仿(4mL)中,並進一步攪拌一整晚。將間氯過苯甲酸(含量:77%, 0.030g, 0.13mmol)加入至反應溶液中,並進一步於室溫下攪拌一整晚。將反應溶液注入飽和碳酸氫鈉水溶液中,並用氯仿進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得5-氯-1-(2-(乙基亞磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(0.090g, 產率:24%)及5-氯-1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑(0.30g, 產率:76%)。
5-氯-1-(2-(乙基亞磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/ TMS δ (ppm)):1.28(3H, t), 2.72(1H, dq), 3.15(1H, dq), 4.29-4.57 (2H, m), 5.05-5.32(1H, m), 7.59(1H, d), 7.62(1H, s), 7.88(1H, dd), 8.43(1H, d)
折射率 n20 D
1.4879
5-氯-1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,4,4,4-六氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.30(3H, t), 3.48(2H, q), 4.29-4.55(2H, m), 5.05-5.32(1H, m), 7.60(1H, d), 7.62(1H, s), 8.06(1H, d), 8.45(1H, s)
折射率 n20 D
1.4721
[實施例22]
1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1737)之製造
1)1-(2-氟-4-(三氟甲基)苯基)-1H-吡唑-4-醇
將2-氟-4-(三氟甲基)苯胺(5.0g, 28mmol)溶解於濃鹽酸(9.3mL, 0.11mol)及水(56mL)中。於冰冷下,依序將亞硝酸鈉(2.5g, 36mmol)的水(14mL)溶液、4-氯乙醯乙酸(3.8g, 28mmol)及乙酸鈉(4.6g, 56mmol)的水(14mL)溶液滴加至此混合物中,並進一步於室溫下攪拌3小時。將反應溶液注入水中,濾取析出的固體,使其乾燥,獲得粗製的1-(3-氯-2-氧代亞丙基)-2-(2-氟-4-(三氟甲基)苯基)肼。將所獲得的粗製的1-(3-氯-2-氧代亞丙基)-2-(2-氟-4-(三氟甲基)苯基)肼溶解於甲醇(30mL)中,加入氫氧化鈉(1.5g, 38mmol),並進一步於室溫下攪拌1小時。將反應溶液注入經冰冷過的稀鹽酸中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-氟-4-(三氟甲基)苯基)-1H-吡唑-4-醇(2.5g, 產率:36%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):4.33(1H, s), 7.46-7.53(3H, m), 7.81-7.82(1H, dd) , 8.06-8.11(1H, m)
2)1-(2-氟-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑
依序將1-(2-氟-4-(三氟甲基)苯基)-1H-吡唑-4-醇(2.0g, 8.1mmol)、碳酸鉀(1.7g, 12mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(4.3g, 8.9mmol)加入至DMF(16mL)中,並進一步於室溫下攪拌一整晚。將反應溶液注入水中,用二異丙醚進行萃取。透過二氧化矽凝膠的短墊來過濾有機層,並用二異丙醚進行溶析。於減壓下蒸餾出溶劑,獲得1-(2-氟-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(3.3g, 產率:95%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):4.44(2H, dd), 7.49-7.55(2H, m), 7.61(1H, s), 7.87 (1H, d), 8.10(1H, t)
3)1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明的化合物)編號:A-1735)
依序將1-(2-氟-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.0g, 2.3mmol)、碳酸鉀(0.84g, 6.1mmol)及乙硫醇(0.35mL, 4.8mmol)加入至DMF(8mL)中,並進一步於室溫下攪拌4小時。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.95g, 產率:86%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.29(3H, t), 2.88(2H, q), 4.43(2H, t), 7.52(2H, s), 7.59(1H, s), 7.63(1H, s), 7.69(1H, s)
熔點 0-30℃
4)1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1737)
於室溫下依序將1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.20g, 0.43mmol)及間氯過苯甲酸(含量:77%, 0.24g, 1.1mmol)加入至氯仿(1mL)中,並進一步攪拌3小時。將反應溶液注入至飽和碳酸氫鈉水溶液中,並用氯仿進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得1-(2-(乙基磺醯基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.19g, 產率:89%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.24(3H, t), 3.25(2H, q), 4.42(2H, tt), 7.61(1H, d), 7.61(1H, s), 7.69(1H, s), 7.98(1H, dd), 8.46(1H, d)
熔點 108-111℃
[實施例23]
1-(2-(N-氰基乙烷亞磺醯亞胺基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:E-0183)之製造
將1-(2-(乙硫基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.6g, 3.4mmol)溶解於甲醇(17mL)中。於冰冷下,依序將氰胺(0.19g, 4.5mmol)、叔丁醇鉀(0.51g, 4.5mmol)及N-溴琥珀醯亞胺(0.93g, 5.2mmol)加入至此混合物中,並進一步於室溫下攪拌一整晚。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用己烷/二異丙醚(10:1)的混合溶劑清洗殘渣,獲得1-(2-(N-氰基乙烷亞磺醯亞胺基)-4-(三氟甲基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.8g, 產率:定量)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.55(3H, t), 3.15(1H, dq), 3.59(1H, dq), 4.48(2H, tt), 7.57(1H, d), 7.66(1H, s), 7.77(1H, s), 7.91(1H, dd), 8.63(1H, d)
熔點 156-159℃
[實施例24]
3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-0412)之製造
1)2-(4-(芐氧基)-1H-吡唑-1-基)-3-氯-5-(三氟甲基)吡啶
將2,3-二氯-5-(三氟甲基)吡啶(4.0g, 19 mmol)及4-(芐氧基)-1H-吡唑(3.3g, 19mmol)溶解於THF(39mL)中。於冰冷下,將叔丁醇鉀(2.3g, 20mmol)加入至此混合物中,並進一步於室溫下攪拌1小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得2-(4-(芐氧基)-1H-吡唑-1-基)-3-氯-5-(三氟甲基)吡啶(4.1g, 產率:63%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):5.04(2H, s), 7.32-7.47(5H, m), 7.68(1H, d), 8.01(1H, d), 8.10(1H, dd), 8.61(1H, dd)
2)2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙硫基)-5-(三氟甲基)吡啶
於室溫下依序將2-(4-(芐氧基)-1H-吡唑-1-基)-3-氯-5-(三氟甲基)吡啶(4.1g, 12mmol)、乙硫醇(0.75mL, 12mmol)及叔丁醇鉀(1.6g, 14mmol)加入至DMF(23mL)中,並進一步攪拌1小時。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙硫基)-5-(三氟甲基)吡啶(4.3g, 產率:98%)。
1
H-NMR數據(300MHz, CDCl3
/ TMS δ (ppm)):1.40(3H, t), 2.96(2H, q), 5.04(2H, s), 7.31-7.46 (5H, m), 7.66(1H, d), 7.80(1H, d), 8.12(1H, d), 8.39(1H, dd)
3)1-(3-(乙硫基)-5-(三氟甲基)吡啶-2-基)-1H-吡唑-4-醇(本發明化合物編號:F-0010)
依序將2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙硫基)-5-(三氟甲基)吡啶(4.3g, 11mmol)及氯化鋁(3.0g, 23mmol)加入至二氯甲烷(55mL)與乙硫醇(11mL)的混合溶劑中,並進一步於加熱回流下攪拌10分鐘。將反應溶液注入檸檬酸水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(3-(乙硫基)-5-(三氟甲基)吡啶-2-基)-1H-吡唑-4-醇(2.3g, 產率:70%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.39(3H, t), 2.96(2H, q), 4.95(1H, s), 7.59(1H, d), 7.81(1H, d), 8.07(1H, d), 8.40(1H, dd)
熔點 121-123℃
4)3-(乙硫基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-0410)
依序將1-(3-(乙硫基)-5-(三氟甲基)吡啶-2-基)-1H-吡唑-4-醇(2.1g, 7.3mmol)、碳酸鉀(1.2g, 8.7mmol)以及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(3.9g, 8.1mmol)加入至乙腈(14mL)中,並進一步於加熱回流下攪拌2小時。濃縮反應溶液,並用二異丙醚/己烷(1:1)的混合溶劑來萃取殘渣。用無水硫酸鎂使有機層乾燥之後,減壓下蒸餾出溶劑,獲得3-(乙硫基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(3.7g, 產率:定量)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.40(3H, t), 2.97(2H, q), 4.45(2H, tt), 7.67(1H, d), 7.83(1H, d), 8.19(1H, d), 8.40(1H, dd)
熔點 71-73℃
5)3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-0412)
將3-(乙硫基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(3.7g, 7.9mmol)溶解於二氯甲烷(14mL)中。於冰冷下,將間氯過苯甲酸(含量:77%, 4.1g, 18mmol)加入至此混合物中,並進一步於室溫下攪拌一整晚。將反應溶液注入10%碳酸鉀水溶液中,並用二氯甲烷進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(3.7g, 產率:94%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.43(3H, t), 4.03(2H, q), 4.46(2H, t), 7.70(1H, d), 8.15(1H, d), 8.79(1H, d), 8.85(1H, d)
熔點 96-99℃
[實施例25]
3-(乙基亞磺醯基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-1077)及3-(乙基磺醯基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-1078)之製造
1)3-(乙硫基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-1076)及2,2'-(4,4'-((2,3,3,3-四氟丙-1-烯-1,1-二基)雙(氧基))雙(1H-吡唑-1-基))雙(3-(乙硫基)-5-(三氟甲基)吡啶)
依序將1-(3-(乙硫基)-5-(三氟甲基)吡啶-2-基)-1H-吡唑-4-醇(0.60g, 2.1mmol)及三乙胺(0.32g, 3.2mmol)加入至二氯甲烷(4.1mL)中,並於六氟丙烯(1.5g, 10mmol)氣氛下於室溫下攪拌3小時。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得3-(乙硫基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶與2,2'-(4,4'-((2,3,3,3-四氟丙-1-烯-1,1-二基)雙(氧基))雙(1H-吡唑-1-基))雙(3-(乙硫基)-5-(三氟甲基)吡啶)之混合物。將碳酸鉀(0.29g, 2.1mmol)及DMF(2.1mL)加入至所獲得的混合物中,並進一步於室溫下攪拌3小時,接著於80℃下攪拌6小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鈉使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠色譜法純化殘渣之後,由正己烷於冷時再結晶而獲得3-(乙硫基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(0.38g, 產率:42%)。濃縮再結晶母液,獲得2,2'-(4,4'-((2,3,3,3-四氟丙-1-烯-1,1-二基)雙(氧基))雙(1H-吡唑-1-基))雙(3-(乙硫基)-5-(三氟甲基)吡啶)(0.090g, 產率:13%)。
3-(乙硫基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.40(3H, t), 2.98(2H, q), 5.03(1H, d sext), 7.77(1H, s), 7.87(1H, d), 8.43(1H, s), 8.43(1H, s)
2,2'-(4,4'-((2,3,3,3-四氟丙-1-烯-1,1-二基)雙(氧基))雙(1H-吡唑-1-基))雙(3-(乙硫基)-5-(三氟甲基)吡啶)
1
H-NMR數據(300MHz,CDCl3
/TMS δ (ppm)):1.39(6H,t), 2.96(4H, q), 7.71(1H, d),7.71(1H, d), 7.84(1H, s), 7.85(1H, s), 8.35(1H, s), 8.35(1H, s), 8.40(1H, s),8.41 (1H, s)
GC-MS數據(EI, m/z):688(M+
)
熔點 120-122℃
2)3-(乙基亞磺醯基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-1077)及3-(乙基磺醯基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-1078)
將3-(乙硫基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(0.28g, 0.64mmol)溶解於二氯甲烷(6.4mL)中。於冰冷下,將間氯過苯甲酸(含量:77%, 0.23g, 1.0mmol)加入至此混合物中,並進一步於室溫下攪拌一整晚。將反應溶液注入碳酸鉀水溶液中,用二氯甲烷進行萃取。用無水硫酸鈉使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙基亞磺醯基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(0.13g, 產率:45%)及3-(乙基磺醯基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶(0.15g, 產率:50%)。
3-(乙基亞磺醯基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.34(3H, t), 2.89(1H, dq), 3.40(1H, dq), 5.05(1H, d sext), 7.77(1H, s), 8.65(1H, d), 8.73-8.74(1H, m), 8.825-8.833(1H, m)
折射率 n20 D
1.4868
3-(乙基磺醯基)-2-(4-(1,1,2,3,3,3-六氟丙氧基)-1H-吡唑-1-基)-5-(三氟甲基)吡啶
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.43(3H, t), 4.02(2H, q), 5.04(1H, d sext), 7.79(1H, s), 8.41(1H, s), 8.81(1H, d), 8.90(1H, d)
折射率 n20 D
1.4704
[實施例26]
3-(乙基亞磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-0792)及3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-0793)之製造
1)1-(3-氯-5-(三氟甲基)吡啶-2-基)-3,5-二甲基-1H-吡唑-4-醇
依序將3-氯-2-肼基-5-(三氟甲基)吡啶(4.5g, 21mmol)及對甲基苯甲酸2,4-二氧戊烷-3-基(5.0g, 21mmol)加入至乙醇(20mL)中,並進一步於加熱回流下攪拌2小時。於減壓下濃縮反應溶液,並用己烷/二異丙醚(10:1)的混合溶劑來清洗殘渣,獲得粗製的對甲基苯甲酸1-(3-氯-5-(三氟甲基)吡啶-2-基)-3,5-二甲基-1H-吡唑-4-基。將所獲得的粗製的對甲基苯甲酸1-(3-氯-5-(三氟甲基)吡啶-2-基)-3,5-二甲基-1H-吡唑-4-基溶解於THF(10mL)中,加入氫氧化鈉(0.80g, 20mmol)的水(10mL)溶液,於60℃下攪拌2小時。將反應溶液注入稀鹽酸中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(3-氯-5-(三氟甲基)吡啶-2-基)-3,5-二甲基-1H-吡唑-4-醇(2.2g, 產率:35%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):2.22(3H, s), 2.27(3H, s), 4.18(1H, br s), 8.12(1H, dd), 8.69(1H, dd)
2)3-氯-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶
於室溫下依序將1-(3-氯-5-(三氟甲基)吡啶-2-基)-3,5-二甲基-1H-吡唑-4-醇(1.4g, 4.8mmol)、碳酸鉀(1.0g, 7.2mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(2.5g, 5.2mmol)加入至乙腈(10mL)中,並進一步攪拌一整晚。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得3-氯-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(2.2g, 產率:97%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):2.25(3H, s), 2.31(3H, s), 4.36(2H, tt), 8.14(1H, dd), 8.71(1H, dd)
3)3-(乙硫基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-0791)
依序將3-氯-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(1.8g, 3.8mmol)、乙硫醇(0.42mL, 5.7mmol)以及氫化鈉(含量:55%, 0.25g, 5.7mmol)加入至DMF(20mL)中,並進一步於80℃下攪拌1小時。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙硫基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(0.45g, 產率:24%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.35(3H, t), 2.307(3H, s), 2.314(3H, s), 2.93(2H, q), 4.37(2H, tt), 7.85(1H, d), 8.49(1H, dd)
折射率 n20 D
1.4748
4)3-(乙基亞磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-0792)及3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:F-0793)
於室溫下將3-(乙硫基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(0.31g, 0.62mmol)及間氯過苯甲酸(含量:77%, 0.22g, 0.98mmol)加入至氯仿(6mL)中,並進一步攪拌3小時。將反應溶液注入飽和碳酸氫鈉水溶液中,並用氯仿進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙基亞磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(0.21g, 產率:66%)及3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶(0.11g, 產率:33%)。
3-(乙基亞磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.39(3H, t), 2.31(3H, s), 2.63(3H, s), 2.84(1H, dq), 3.47(1H, dq), 4.36(2H, tt), 8.71(1H, dd), 8.78(1H, d)
折射率 n20 D
1.4755
3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-3,5-二甲基-1H-吡唑-1-基)-5-(三氟甲基)吡啶
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.40(3H, t), 2.29(3H, s), 2.38(3H, t), 3.90(2H, q), 4.37(2H, tt), 8.73(1H, dd), 8.94(1H, dd)
熔點 86-88℃
[實施例27]
3-(乙基亞磺醯基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:K-2029)及3-(乙基磺醯基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:K-2030)之製造
1)1-(3-氯-5-(三氟甲基)吡啶-2-基)-1H-1,2,4-三唑-3-醇
依序將2,3-二氯-5-(三氟甲基)吡啶(10.0g, 46.3mmol)、氨基脲鹽酸鹽(10.3g, 92.4mmol)及N,N-二異丙基乙胺(16.2mL, 51.1mmol)加入至N-甲基吡咯烷酮(46mL)中,並進一步於100℃下攪拌4小時。將原甲酸三甲酯(46mL)加入至反應溶液中,並進一步於加熱回流下攪拌4小時。濃縮反應溶液,注入稀鹽酸中。濾取析出的固體,依序用水及己烷清洗。於減壓下進行加熱乾燥,獲得1-(3-氯-5-(三氟甲基)吡啶-2-基)-1H-1,2,4-三唑-3-醇(5.46g, 產率:45%)。
1
H-NMR數據(300 MHz, DMSO-d6
/TMS δ (ppm)):8.50(1H, dd), 8.74(1H, s), 8.83(1H, dd)
2)1-(3-(乙硫基)-5-(三氟甲基)吡啶-2-基)-1H-1,2,4-三唑-3-醇(本發明化合物編號:K-1979)
依序將1-(3-氯-5-(三氟甲基)吡啶-2-基)-1H-1,2,4-三唑-3-醇(5.5g, 21mmol)及乙硫醇鈉(2.6g, 31mmol)加入至N-甲基吡咯烷酮(100mL)中,並進一步於室溫下攪拌一整晚。將反應溶液注入稀鹽酸中,濾取析出的固體,依序用水、己烷、丙酮清洗。於減壓下進行加熱乾燥,獲得1-(3-(乙硫基)-5-(三氟甲基)吡啶-2-基)-1H-1,2,4-三唑-3-醇(2.5g, 產率:41%)。
1
H-NMR數據(300MHz, DMSO-d6
/TMS δ (ppm)):1.23(3H, t), 3.12(2H, q), 8.22(1H, d), 8.68(1H, Dd), 8.83(1H, s), 11.7(1H, br s)
熔點 230-233℃
3)3-(乙硫基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:K-2028)
於室溫下依序將1-(3-(乙硫基)-5-(三氟甲基)吡啶-2-基)-1H-1,2,4-三唑-3-醇(0.35g, 1.2mmol)、碳酸鉀(0.25g, 1.8mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(0.64g, 1.3mmol)加入至DMF(12mL)中,並進一步攪拌2小時。將反應溶液注入水中,用二氯甲烷進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得3-(乙硫基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(0.53g, 產率:93%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.40(3H, t), 3.00(2H, q), 4.91(2H, t), 7.88(1H, d), 8.46(1H, d), 8.75(1H, s)
熔點 69-71℃
4)3-(乙基亞磺醯基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:K-2029)及3-(乙基磺醯基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(本發明化合物編號:K-2030)
於室溫下依序將3-(乙硫基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(0.45g, 0.95mmol)及間氯過苯甲酸(含量:77%, 0.34g, 1.5mmol)加入至氯仿(10mL)中,並進一步攪拌一整晚。將反應溶液注入飽和碳酸氫鈉水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙基亞磺醯基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(0.060g, 產率:13%)及3-(乙基磺醯基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶(0.32g, 產率:67%)。
3-(乙基亞磺醯基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.33(3H, t), 2.88(1H, dq), 3.37(1H, dq), 4.91(2H, t), 8.75(1H, d), 8.83(1H, d), 9.06(1H, s)
熔點 77-78℃
3-(乙基磺醯基)-2-(3-(2,2,3,3,4,4,4-七氟丁氧基)-1H-1,2,4-三唑-1-基)-5-(三氟甲基)吡啶
1
H-NMR數據(300MHz, CDCl3
/ TMS δ (ppm)):1.44(3H, t), 3.94(2H, q), 4.90(2H, t), 8.76(1H, s), 8.82(1H, d), 8.95(1H, d)
熔點 74-76℃
[實施例28]
1-(4-溴-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1681)之製造
1)4-溴-2-(乙硫基)苯胺
依序將2-氨基-6-溴苯並噻唑(30g, 0.13mol)及氫氧化鉀(含量:85%, 43g, 0.65mol)加入至水(43mL)中,並進一步於加熱回流下攪拌3小時。用冰冷卻反應溶液,依序加入甲醇(39mL)及乙基碘(22g, 0.14mol),並進一步於室溫下攪拌一整晚。將反應溶液注入水中,並用二異丙醚進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得4-溴-2-(乙硫基)苯胺(29g, 產率:95%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.24(3H, t), 2.77(2H, q), 4.33(2H, br s), 6.60(1H, d), 7.18(1H, dd), 7.47(1H, d)
2)1-(4-溴-2-(乙硫基)苯基)-1H-吡唑-4-醇(本發明化合物編號:D-0030)
將4-溴-2-(乙硫基)苯胺(15g, 65mmol)溶解於乙酸(258mL)及水(65mL)的混合溶劑中。於冰冷下,依序將亞硝酸鈉(5.3g, 77mmol)及4-氯乙醯乙酸(9.7g, 71mmol)加入此混合物中,並進一步於室溫下攪拌1小時。將反應溶液注入水中,濾取析出的固體,並使其乾燥,獲得粗製的2-(4-溴-2-(乙硫基)苯基)-1-(3-氯-2-氧代亞丙基)肼。將所獲得的粗製的2-(4-溴-2-(乙硫基)苯基)-1-(3-氯-2-氧代亞丙基)肼溶解於甲醇(129mL)中,並於室溫下加入氫氧化鈉(5.2g, 130mmol)攪拌3小時。於減壓下蒸餾出溶劑,並加入稀鹽酸直到pH達到1。濾取析出的固體,並依序用水及己烷清洗,於減壓下進行加熱乾燥,獲得1-(4-溴-2-(乙硫基)苯基)-1H-吡唑-4-醇(18g, 產率:93%)。
1
H-NMR數據(300MHz, DMSO-d6
/TMS δ (ppm)):1.17(3H, t), 2.94(2H, q), 7.28(1H, d), 7.33(1H, D), 7.45(1H, dd), 7.49(1H, d), 7.58(1H, d), 8.81(1H, br s)
熔點 141-143℃
3)1-(4-溴-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1681)
依序將1-(4-溴-2-(乙硫基)苯基)-1H-吡唑-4-醇(10g, 33mmol)、碳酸鉀(6.9g, 50mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(18g, 37mmol)加入至乙腈(66mL)中,並進一步於加熱回流下攪拌4小時。透過二氧化矽凝膠的短墊來過濾反應溶液,並用二異丙醚進行溶析。於減壓下蒸餾出溶劑,獲得1-(4-溴-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(16g, 產率:99%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.28(3H, t), 2.84(2H, q), 4.42(2H, tt), 7.24(1H, d), 7.38(1H, dd), 7.50(1H, d), 7.55(1H, s), 7.57(1H, s)
[實施例29]
N-(S,S-二甲基亞硫烷基)-3-(乙基磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯胺(本發明化合物編號:A-3111)之製造
1)N-(S,S-二甲基硫烷基)-3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑- 1-基)苯胺(本發明化合物編號:A-3109)
依序將1-(4-溴-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.0g, 2.1mmol)、S,S-二甲基亞碸基亞胺(0.23g, 2.5mmol)、三(二亞苄基丙酮)二鈀(0)(0.038g, 0.041mmol)、4,5-雙二苯基膦-9,9-二甲基氧雜蒽(Xantphos)(0.048g, 0.083mmol)及碳酸銫(1.0g, 3.1mmol)加入至1,4-二噁烷(10mL)中,並進一步於加熱回流下攪拌8小時。將S,S-二甲基亞碸基亞胺(0.23g, 2.5mmol)、三(二亞苄基丙酮)二鈀(0)(0.057g, 0.062mmol)及4,5-雙二苯基膦-9,9-二甲基氧雜蒽(0.072g, 0.12mmol) 加入至反應溶液中,並進一步於加熱回流下攪拌8小時。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得N-(S,S-二甲基硫烷基)-3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1- 基)苯胺(0.53g, 產率:52%)。
1
H-NMR數據 (300MHz, CDCl3
/TMS δ (ppm)):1.26 (3H, t), 2.81 (2H, q), 3.19 (6H, s), 4.41 (2H, tt), 6.95 (1H, dd), 7.08 (1H, d), 7.20 (1H, d), 7.507 (1H, s), 7.514 (1H, s)
折射率 n20 D
1.5335
2)N-(S,S-二甲基亞硫烷基)-3-(乙基磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯胺(本發明化合物編號:A-3111)
於室溫下依序將N-(S,S-二甲基亞硫烷基)-3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯胺(0.43g, 0.87mmol)及間氯過苯甲酸(含量:77%, 0.39g, 1.7mmol)加入至氯仿(9mL)中,並進一步攪拌一整晚。將反應溶液注入碳酸鉀水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得N-(S,S-二甲基亞硫烷基)-3-(乙基磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯胺(0.45g, 產率:98%)。
1
H-NMR數據 (300MHz, CDCl3
/TMS δ (ppm)):1.21 (3H, t), 3.09 (2H, q), 3.22 (6H, s), 4.40 (2H, t), 7.28 (1H, d), 7.40 (1H, dd), 7.52 (1H, s), 7.56 (1H, s), 7.76 (1H, d)
折射率 n20 D
1.5228
[實施例30]
3-(乙基亞磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟(本發明化合物編號:A-3137)及3-(乙基磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟(本發明化合物編號:A-3138)之製造
1)3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛(本發明化合物編號:A-3112)
依序將1-(4-溴-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(3.0g, 6.2mmol)、三乙基矽烷(2.0mL, 13mmol)、碳酸鈉(0.66g, 6.2mmol)、二氯[1,1'-雙(二苯基膦基)二茂鐵]鈀(II)二氯甲烷加合物(0.25g, 0.31mmol)以及DMF(12mL)加入至不鏽鋼製的耐壓容器(高壓釜)中,用一氧化碳置換容器內部。將一氧化碳(表壓9 kgf/cm2
)填充至容器內部,並進一步以100℃攪拌8小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛(2.0g, 產率:75%)。
1
H-NMR數據 (300 MHz, CDCl3
/TMS δ (ppm)): 1.31(3H, t), 2.93 (2H, q), 4.44(2H, t), 7.58-7.61(2H, m), 7.75(1H, dd), 7.75 (1H, d), 7.92(1H, d), 10.0(1H, s)
2)3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛肟(本發明化合物編號:A-3124)
依序將3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛(2.0g, 4.6mmol)、鹽酸羥胺(0.39g, 5.6mmol)及乙酸鈉(0.57g, 7.0mmol)加入至乙醇(23mL)中,並進一步於加熱回流下攪拌1小時。濃縮反應溶液,用乙酸乙酯萃取殘渣。依序用水及飽和食鹽水清洗有機層,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛肟(2.2g, 產率:定量)。
1
H-NMR數據 (300 MHz, CDCl3
/TMS δ (ppm)):1.27(3H, t), 2.85(2H, q), 4.43(2H, tt), 7.39-7.46(2H, m), 7.57(1H, d), 7.63-7.66(2H, m), 7.74(1H, s), 8.13(1H, s)
折射率 n20 D
1.5314
3)3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2)-三氟乙基)肟(本發明化合物編號:A-3136)
依序將3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛肟(1.0g, 2.2mmol)、碳酸鉀(0.47g, 3.4mmol)及三氟甲磺酸2,2,2-三氟乙基(0.63g, 2.7mmol)加入至DMF(11mL)中,並進一步於80℃下攪拌4小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟(0.80g, 產率:68%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.27(3H, t), 2.84(2H, q), 4.43(2H, tt), 4.55(2H, q), 7.42(1H, d), 7.47(1H, dd), 7.57(1H, s), 7.64(1H, d), 7.67(1H, s), 8.17 (1H, s)
折射率 n20 D
1.4933
4)3-(乙基亞磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟(本發明化合物編號:A-3137)及3-(乙基磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟(本發明化合物編號:A-3138)
於室溫下依序將3-(乙硫基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟(0.69g, 1.3mmol)及間氯過苯甲酸(含量:77%, 0.47g, 2.1mmol)加入至二氯甲烷(13mL)中,並進一步攪拌一整晚。將反應溶液注入至碳酸鉀水溶液中,並用二氯甲烷進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙基亞磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟(0.18g, 產率:25%)及3-(乙基磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟(0.48g, 產率:66%)。
3-(乙基亞磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2-三氟乙基)肟
1
H-NMR數據 (300 MHz, CDCl3
/TMS δ (ppm)):1.32(3H, t), 2.70-2.82(1H, m), 3.20-3.34(1H, m) , 4.44(2H, t), 4.56(2H, q), 7.41(1H, d), 7.58(1H, s), 7.68(1H, s), 7.85(1H, dd), 8.26(1H, s), 8.31(1H, d)
熔點 88-90℃
3-(乙磺醯基)-4-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)苯甲醛O-(2,2,2- 三氟乙基)肟
1
H-NMR數據(300MHz, CDCl3
/TMSδ(ppm)):1.24(3H, t), 3.22(2H, q), 4.42(2H, tt), 4.59(2H, q), 7.49(1H, d), 7.59(1H, d), 7.67(1H, d), 7.98(1H, dd), 8.26(1H, s), 8.35 (1H, d)
熔點 65-57℃
[實施例31]
1-(2-(乙硫基)-4-碘苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1684)之製造
1)2-氨基-6-碘苯並噻唑
於室溫下依序將4-碘苯胺(25.0g, 0.114mol)及硫氰酸鉀(44.3g, 0.456mol)加入至乙酸(175mL)中,並進一步攪拌20分鐘。將反應溶液保持為內溫10℃的同時,滴加溴(18.4g, 0.115mol)的乙酸(75mL)溶液,並進一步於室溫下攪拌一整晚,接著於70℃下攪拌2小時。將反應溶液注入冰水中,並加入氨水(345mL)。將乙酸乙酯加入至所獲得的混合物中,過濾掉不溶解物,用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得2-氨基-6-碘苯並噻唑(9.3g, 產率:30%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):5.29(2H, br s), 7.29(1H, d), 7.59(1H, dd), 7.89(1H, d)
2)6-碘苯並噻唑
將2-氨基-6-碘苯並噻唑(4.9g, 18mmol)溶解於THF(35mL)中。於加熱回流下,將亞硝酸叔丁酯(含量:90%, 2.4g, 21mmol)滴加至此混合物中,並進一步於加熱回流下攪拌1小時。將亞硝酸叔丁酯(含量:90%, 1.6g, 14mmol)加入至反應溶液中,並進一步於加熱回流下攪拌10分鐘。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得6-碘苯並噻唑(2.8g, 產率:60%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):7.81(1H, dd), 7.88(1H, d), 8.32(1H, d), 8.93(1H, s)
3)2-(乙硫基)-4-碘苯胺
依序將6-碘苯並噻唑(2.8g, 11mmol)及肼一水合物(4.0g, 80mmol)加入至乙醇(50mL)中,並進一步於加熱回流下攪拌6小時。用冰冷反應溶液,依序加入叔丁醇鉀(1.2g, 11mmol)及碘乙烷(1.7g, 11mmol),並進一步於室溫下攪拌2小時。將反應溶液注入水中,並用二異丙醚進行萃取。依序用水及飽和食鹽水清洗有機層。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得2-(乙硫基)-4-碘苯胺(2.7g, 產率:90%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.23(3H, t), 2.76(2H, q), 4.36(2H, br s), 6.50(1H, d), 7.35(1H, dd), 7.65(1H, d)
4)1-(2-(乙硫基)-4-碘苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1684)
根據實施例3(3)及實施例3(4)的方法,並使用2-(乙硫基)-4-碘苯胺(4.7 g,17 mmol)來取代4-(芐氧基)-2-(乙硫基)苯胺,獲得1-(2-(乙硫基)-4-碘苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(2.5g, 產率:28%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.27(3H, t), 2.81(2H, q), 4.41(2H, tt), 7.10(1H, d), 7.55(1H, s), 7.57(1H, dd), 7.58(1H, s), 7.69(1H, d)
熔點 43-45℃
[實施例32]
1-(4-環丙基-2-(乙基亞磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1751)及1-(4-環丙基-2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1752)之製造
1)1-(4-環丙基-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1750)
依序將1-(2-(乙硫基)-4-碘苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.1g, 2.1mmol)、環丙硼酸(0.27g, 3.1mmol)、乙酸鈀(II)(0.047g, 0.21mmol)、磷酸三鉀(1.6g, 7.5mmol)以及三環己基膦(0.6mol/L甲苯溶液,0.70mL, 0.42mmol)加入至甲苯(9mL)與水(1mL)的混合物中,並進一步於加熱回流下攪拌4.5小時。將反應溶液加入至檸檬酸水溶液中,並用己烷/乙酸乙酯(1:1)的混合溶劑進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(4-環丙基-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.55g, 產率:60%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):0.70-0.75(2H, m), 0.99-1.06(2H, m), 1.23(3H, t), 1.88-1.97(1H, m), 2.76(2H, q), 4.41(2H, t), 6.93(1H, dd), 7.14(1H, d), 7.25(1H, d), 7.52(1H, s), 7.56(1H, s)
折射率 n20 D
1.5101
2)1-(4-環丙基-2-(乙基亞磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1751)及1-(4-環丙基-2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-1752)
於室溫下依序將1-(4-環丙基-2-(乙硫基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.41g, 0.93mmol)及間氯過苯甲酸(含量:77%, 0.33g, 1.5mmol)加入至氯仿(5mL)中,並進一步攪拌一整晚。將反應溶液注入至硫代硫酸鈉水溶液中,加入飽和碳酸氫鈉,並用氯仿進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(4-環丙基-2-(乙基亞磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.18g, 產率:42%)及1-(4-環丙基-2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.21g, 產率:48%)。
1-(4-環丙基-2-(乙基亞磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):0.76-0.86(2H, m), 1.02-1.12(2H, m), 1.28(3H, t) , 1.99-2.08(1H, m), 2.67(1H, dq), 3.14(1H, dq), 4.42(2H, tt), 7.21(1H, dd), 7.26(1H, d), 7.51(1H, d), 7.56(1H, d), 7.81(1H, d)
折射率 n20 D
1.5128
1-(4-環丙基-2-(乙基磺醯基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):0.79-0.85(2H, m), 1.10-1.17(2H, m), 1.20(3H, t), 2.00-2.09(1H, m), 3.09(2H, q), 4.40(2H, tt), 7.32(1H, d), 7.38(1H, dd), 7.54(1H, d), 7.59(1H, d) 7.84(1H, d)
折射率 n20 D
1.4936
[實施例33]
1-(2-(乙基磺醯基)-4-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2145)之製造
1)1-(2-(乙硫基)-4-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(本發明化合物編號:A-2143)
依序將1-(2-(乙硫基)-4-碘苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(1.0g, 1.9mmol)、磷酸三鉀(0.80g, 3.8mmol)、1,2,4-三唑(0.20g, 2.9mmol)、碘化銅(0.18g, 0.94mmol)及N,N'-二甲基乙二胺(0.17g, 1.9mmol)加入至N-甲基吡咯烷酮(10mL)中,並進一步於130℃下攪拌8小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用稀氨水來清洗有機層,並用無水硫酸鎂使其乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)-4-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,3,4,4,4-七氟丁氧基)-1H-吡唑(0.58g, 產率:65%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.32(3H, t), 2.92(2H, q), 4.44(2H, tt), 7.52-7.53(2H, m), 7.59(1H, s), 7.65(1H, s), 7.77(1H, dd), 8.14(1H, s), 8.60(1H, s)
熔點 108-110℃
2)1-(2-(乙基磺醯基)-4-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,4-庚基氟丁氧基)-1H-吡唑(本發明化合物編號:A-2145)
將1-(2-(乙硫基)-4-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(16.5g, 35.2mmol)溶解於氯仿(170mL)中。於冰冷下,將間氯過苯甲酸(含量:77%, 16.5g, 73.6mmol)加入至此混合物中,並進一步於室溫下攪拌一整晚。將反應溶液注入至碳酸鉀水溶液中,並用氯仿進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。使殘渣在熱時由乙酸乙酯/己烷的混合溶劑再結晶,獲得1-(2-(乙基磺醯基)-4-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑(15.6g, 產率:89%)。
1
H-NMR數據(300MHz, CDCl3
/ TMS δ (ppm)):1.27(3H, t), 3.23(2H, q), 4.43(2H, tt), 7.62(1H, d), 7.66(1H, s), 7.69(1H, s), 8.14(1H, d) 8.18(1H, s), 8.48(1H, d), 8.74(1H, s)
熔點 95-97℃
[實施例34]
1-(2-(乙基亞磺醯基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-辛基氟戊氧基)-1H-吡唑(本發明化合物編號:B-0998)及1-(2-(乙基磺醯基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-八氟戊氧基)-1H-吡唑(本發明化合物編號:B-0999)之製造
1)1-(乙硫基)-4-氟-2-硝基苯
將2,5-二氟硝基苯(10g, 63mmol)溶解於DMF(63mL)中。於冰冷下,依序將乙硫醇(3.9g, 63mmol)及碳酸鉀(10g, 72mmol)加入至此混合物中,並進一步於室溫下攪拌一整晚。將反應溶液注入至水中,濾取析出的固體,並用水清洗。於減壓下進行加熱乾燥,獲得1-(乙硫基)-4-氟-2-硝基苯(12g, 產率:95%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.40(3H, t), 2.99(2H, q), 7.33(1H, ddd), 7.40(1H, dd), 7.94(1H, dd)
2)2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯胺
依序將1-(乙硫基)-4-氟-2-硝基苯(12g, 0.060 mol)及1,2,4-三唑鈉(6.7g, 0.074mol)加入至N-甲基吡咯烷酮(60mL)中,並進一步於120℃下攪拌6小時。將反應溶液注入至水中,濾取析出的固體,獲得粗製的1-(4-(乙硫基)-3-硝基苯基)-1H-1,2,4-三唑。將所獲得的粗製的1-(4-(乙硫基)-3-硝基苯基)-1H-1,2,4-三唑及鐵粉(10g, 0.18mol)加入至乙酸(120mL)與乙醇(120mL)的混合溶液中,並進一步於加熱回流下攪拌1小時。將反應溶液注入碳酸鉀水溶液中,並將乙酸乙酯加入至殘渣中。透過矽藻土過濾,依序用碳酸鉀水溶液及飽和食鹽水來清洗有機層。用無水硫酸鎂使有機層乾燥之後,蒸餾出溶劑,獲得2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯(11g, 產率:84%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.25(3H, t), 2.79(2H, q), 6.94(1H, dd), 7.09(1H, d), 7.48(1H, d), 8.09(1H, s), 8.55(1H, s)
3)1-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-1H-吡唑-4-醇(本發明化合物編號:D-0805)
將2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯胺(5.0g, 23mmol)溶解於乙酸(180mL)與水(20mL)的混合溶劑中。於冰冷下,依序將亞硝酸鈉(1.9g, 28mmol)的水(20mL)溶液及4-氯乙醯乙酸(3.7g, 27mmol)加入此混合物中,並進一步於室溫下攪拌1小時。將反應溶液注入水中,濾取析出的固體,獲得粗製的2-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-1-(3-氯-2-氧代亞丙基)肼。依序將所獲得的粗製的2-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-1-(3-氯-2-氧代亞丙基)肼及氫氧化鈉(1.8g, 45mmol)加入至甲醇(45mL)中,並進一步於室溫下攪拌3小時。將反應溶液注入稀鹽酸中,濾取析出的固體,並依序用水及二異丙醚進行清洗。於減壓下進行加熱乾燥,獲得1-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-1H-吡唑-4-醇(5.7g, 產率:87%)。
1
H-NMR數據(300MHz, DMSO-d6
/TMS δ (ppm)):1.19(3H, t), 2.95(2H, q), 7.39(1H, d), 7.63(1H, D), 7.65(1H, dd), 7.87(1H, dd), 7.89(1H, s), 8.26(1H, s), 8.89(1H, br s), 9.38(1H, s)
熔點 137-140℃
4)1-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-八氟戊氧基)-1H-吡唑(本發明化合物編號:B-0977)
依序將1-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-1H-吡唑-4-醇(1.0g, 3.5mmol)、碳酸鉀(0.72g, 5.2mmol)以及九氟丁烷磺酸2,2,3,3,4,4,5,5-八氟戊基(2.0g, 3.9mmol)加入至乙腈(7mL)中,並進一步於加熱回流下攪拌1小時。濃縮反應溶液,用矽膠柱色譜法純化殘渣,獲得1-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-八氟戊氧基)-1H-吡唑(1.3g, 產率:74%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.28(3H, t), 2.86(2H, q), 4.44(2H, tt), 6.09(1H, tt), 7.55(1H, d), 7.59(1H, d), 7.69(1H, dd), 7.74(1H, d), 7.78(1H, d), 8.11 (1H, s), 8.58(1H, s)
熔點 71-73℃
5)1-(2-(乙基亞磺醯基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-八氟戊氧基)-1H-吡唑(本發明化合物編號:B-0998)及1-(2-(乙基磺醯基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-辛基氟戊氧基)-1H-吡唑(本發明化合物編號:B-0999)
於室溫下依序將1-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-八氟戊氧基)-1H-吡唑(0.50g, 1.0mmol)及間氯過苯甲酸(含量:77%, 0.36g, 1.6mmol)加入至二氯甲烷(10mL)中,並進一步攪拌一整晚。將反應溶液注入碳酸鉀水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙基亞磺醯基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-辛基氟戊氧基)-1H-吡唑(0.17g, 產率:33%)及1-(2-(乙基磺醯基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-辛基氟戊氧基)-1H-吡唑(0.35g, 產率:66%)。
1-(2-(乙基亞磺醯基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-辛基氟戊氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.33(3H, t), 2.80(1H, dq), 3.27(1H, dq), 4.46(2H, tt), 6.09(1H, tt), 7.60(1H, d), 7.76(1H, d), 7.80(1H, dd), 7.87(1H, d), 8.16 (1H, s), 8.31(1H, d), 8.70(1H, s)
熔點 139-142℃
1-(2-(乙基磺醯基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-辛基氟戊氧基)-1H-吡唑
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.25(3H, t), 3.22(2H, q), 4.44(2H, t), 6.09(1H, tt), 7.62(1H, d), 7.75(1H, d), 7.90(1H, d), 7.96(1H, dd), 8.17(1H, s), 8.33 (1H, d), 8.72(1H, s)
熔點 74-76℃
[實施例35]
1-(2-(乙磺醯亞胺基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-八氟戊氧基)-1H-吡唑(本發明化合物編號:E-0976)之製造
依序將1-(2-(乙硫基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-八氟戊氧基)-1H-吡唑(0.55g, 1.1mmol)、氨基甲酸銨(0.17g, 2.2mmol)及(二乙醯氧碘)苯(0.88g, 2.7mmol)加入至甲醇(11mL)中,並進一步於室溫下攪拌1小時。將反應溶液注入硫代硫酸鈉水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得1-(2-(乙磺醯亞胺基)-5-(1H-1,2,4-三唑-1-基)苯基)-4-(2,2,3,3,4,4,5,5-八氟戊氧基)-1H-吡唑(0.45g, 產率:77%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.28(3H, t), 2.83(1H, br s), 3.33(2H, dq), 4.44(2H, tt), 6.09(1H, tt), 7.61(1H, s), 7.75(1H, s), 7.86(1H, d), 7.93(1H, dd), 8.16(1H, s), 8.36(1H, d), 8.71(1H, s)
熔點 121-123℃
[實施例36]
3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6(1H-1,2,4-三唑-1-基)吡啶(本發明化合物編號:F-1771)之製造
1)2-氨基-3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶
依序將3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶-2-羧酸(21.5g, 76.2mmol)、二苯基磷醯基疊氮化物(22.0g, 79.9mmol)以及三乙胺(12.7mL, 91.6mmol)加入至叔丁醇(150mL)中,並進一步於100℃下攪拌4小時。將反應溶液注入飽和碳酸氫鈉水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得粗製的(3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶-2-基)氨基甲酸叔丁酯。將所獲得的粗製的(3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶-2-基)氨基甲酸叔丁酯溶解於二氯甲烷(100mL)中,加入三氟乙酸(17mL),並進一步於室溫下攪拌一整晚。濃縮反應溶液,並用飽和碳酸氫鈉水溶液中和。用乙酸乙酯萃取殘渣,並用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得2-氨基-3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶(11.7g, 產率:61%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.33(3H, t), 3.20(2H, q), 5.96(2H, br s), 7.37(1H, d), 8.10(1H, s), 8.13(1H, d), 9.09(1H, s)
熔點 149-151℃
2)3-(乙基磺醯基)-2-氟-6-(1H-1,2,4-三唑-1-基)吡啶
將2-氨基-3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶(7.22g, 28.5mmol)溶解於氯仿(143mL)中。於冰冷下,將四氟硼酸亞硝基酯(5.00g, 42.8mmol)至此混合物中,並進一步於冰冷下攪拌30分鐘,接著於加熱回流下攪拌4小時。將反應溶液注入冰水中,並用氯仿進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(乙基磺醯基)-2-氟-6-(1H-1,2,4-三唑-1-基)吡啶(4.01g, 產率:55%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.37(3H, t), 3.39(2H, q), 8.00(1H, dd), 8.16(1H, s), 8.56(1H, dd), 9.14(1H, s)
熔點 152-155℃
3)2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙基磺醯基)-6-(1H-1,2,4-丁三唑-1-基)吡啶
依序將3-(乙基磺醯基)-2-氟-6-(1H-1,2,4-三唑-1-基)吡啶(4.01g, 15.6mmol)、4-(芐氧基)-1H-吡唑(2.72g, 15.6mmol)以及碳酸鉀(2.58g, 18.7mmol)加入至DMF(160mL)中,並進一步於室溫下攪拌一整晚。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶(6.42g, 產率:定量)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.40(3H, t), 3.99(2H, q), 5.07(2H, s), 7.32-7.48 (5H, m), 7.66(1H, d), 7.91(1H, d), 7.93(1H, d), 8.17(1H, s), 8.71(1H, d) , 9.11(1H, s)
4)1-(3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶-2-基)-1H-吡唑-4-醇(本發明化合物編號:F-0111)
於室溫下依序將2-(4-(芐氧基)-1H-吡唑-1-基)-3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶(2.37g, 5.77mmol)及氯化鋁(1.92g, 14.4mmol)加入至硝基甲烷(12mL)中,並進一步攪拌一整晚。將反應溶液注入10%羅謝爾(Rochelle)鹽水溶液中,濾取析出的固體,依序用水及己烷進行清洗。於減壓下使其乾燥,獲得1-(3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶-2-基)-1H-吡唑-4-醇(1.62g, 產率:88%)。
1
H-NMR數據(300MHz, DMSO-d6
/TMS δ (ppm)):1.31(3H, t), 3.98(2H, q), 7.59(1H, d), 7.98(1H, d), 8.17(1H, d), 8.24(1H, d), 8.72(1H, d), 9.48(1H, s)
熔點 222-225℃
5)3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6-(1H-1,2,4-三唑-1-基)吡啶(本發明化合物編號:F-1771)
於室溫下依序將1-(3-(乙基磺醯基)-6-(1H-1,2,4-三唑-1-基)吡啶-2-基)-1H-吡唑-4-醇(1.62g, 5.06mmol)、碳酸鉀(1.05g, 7.60mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(2.69g, 5.58mmol)加入至DMF(25mL)中,並進一步攪拌2小時。將反應溶液注入水中,用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。使殘渣在熱時由乙酸乙酯/己烷的混合溶劑中再結晶,獲得3-(乙基磺醯基)-2-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6-(1H-1,2, 4-三唑-1-基)吡啶(1.85g, 產率:73%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.41(3H, t), 3.96(2H, q), 4.48(2H, tt), 7.68(1H, d), 8.00(1H, d), 8.02(1H, d), 8.18(1H, s), 8.72(1H, d), 9.16(1H, s)
熔點 77-80℃
[實施例37]
4-(乙基磺醯基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6(1H-1,2,4-三唑-1-基)噠嗪(本發明化合物編號:J-0172)之製造
1)3-(4-(芐氧基)-1H-吡唑-1-基)-4,6-二氯噠嗪
將3,6-二氯噠嗪N-氧化物(5.0g, 30mmol)及4-(芐氧基)-1H-吡唑(5.3g, 30mmol)溶解於THF(150mL)中。於冰冷下,將叔丁醇鉀(4.1g, 37mmol)加入至此混合物中,並進一步於室溫下攪拌1小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得粗製的3-(4-(芐氧基)-1H-吡唑-1-基)-6-氯噠嗪N-氧化物。將所獲得的粗製的3-(4-(芐氧基)-1H-吡唑-1-基)-6-氯噠嗪N-氧化物溶解於氯仿(55mL)中,加入三氯氧磷(5.2mL, 56mmol),並進一步於加熱回流下攪拌3小時。濃縮反應溶液,加入三氯氧磷(7.8mL, 83mmol),並進一步於120℃下攪拌2小時。將反應溶液注入水中,並用二氯甲烷進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(4-(芐氧基)-1H-吡唑-1-基)-4,6-二氯噠嗪(4.1g, 產率:42%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):5.04(2H, s), 7.32-7.46(5H, m), 7.70(1H, d), 7.73 (1H, s), 8.07(1H, d)
2)3-(4-(芐氧基)-1H-吡唑-1-基)-6-氯-4-(乙硫基)噠嗪
將3-(4-(芐氧基)-1H-吡唑-1-基)-4,6-二氯噠嗪(4.0g, 12mmol)溶解於DMF(25mL)中。於冰冷下,將乙硫醇鈉(1.2g, 14mmol)加入至此混合物中,並進一步於冰冷下攪拌2小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得3-(4-(芐氧基)-1H-吡唑-1-基)-6-氯-4-(乙硫基)噠嗪(2.2g, 產率:51%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.44(3H, t), 2.93(2H, q), 5.04(2H, s), 7.29(1H, s), 7.34-7.46(5H, m), 7.66(1H, d), 8.21(1H, d)
3)1-(6-氯-4-(乙硫基)噠嗪-3-基)-1H-吡唑-4-醇(本發明化合物編號:J-0006)
依序將3-(4-(芐氧基)-1H-吡唑-1-基)-6-氯-4-(乙硫基)噠嗪(2.2g, 6.3mmol)及氯化鋁(1.7g, 13mmol)加入至硝基甲烷(32mL)中,並進一步於室溫下攪拌一整晚。將反應溶液注入至6mol/L鹽酸中,濾取析出的固體,並依序用水及己烷進行清洗。於減壓下使其乾燥,獲得1-(6-氯-4-(乙硫基)噠嗪-3-基)-1H-吡唑-4-醇(1.2g, 產率:74%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.47(3H, t), 2.96(2H, q), 7.35(1H, s), 7.66(1H, d), 8.82(1H, d)
熔點 218-221℃
4)6-氯-4-(乙硫基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)噠嗪(本發明化合物編號:J-0113)
於室溫下依序將1-(6-氯-4-(乙硫基)噠嗪-3-基)-1H-吡唑-4-醇(0.75g, 2.9mmol)、碳酸鉀(0.61g, 4.4mmol)及九氟丁烷磺酸2,2,3,3,4,4,4-七氟丁基(1.5g, 3.1mmol)加入至DMF(15mL)中,並進一步攪拌一整晚。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得6-氯-4-(乙硫基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)噠嗪(0.95g, 產率:74%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.45(3H, t), 2.95(2H, q), 4.45(2H, tt), 7.33(1H, s), 7.68(1H, d), 8.29(1H, d)
熔點 45-47℃
5)4-(乙硫基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6-(1H-1,2,4-三唑-1-基)噠嗪(本發明化合物編號:J-0170)
依序將6-氯-4-(乙硫基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)噠嗪(0.35g, 0.80mmol)及1,2,4-三唑鈉(0.080g, 0.88mmol)加入至DMF(4mL)中,並進一步於80℃下攪拌3小時。將反應溶液注入水中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑。用矽膠柱色譜法純化殘渣,獲得4-(乙硫基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6-(1H-1,2,4-三唑-1-基)噠嗪(0.22g, 產率:59%)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.50(3H, t), 3.08(2H, q), 4.47(2H, tt), 7.72(1H, d), 8.01(1H, s), 8.18(1H, s), 8.32(1H, d), 9.34(1H, s)
熔點 188-190℃
6)4-(乙磺醯基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6-(1H-1,2,4-三唑-1-基)噠嗪(本發明化合物編號:J-0172)
於室溫下依序將4-(乙硫基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6-(1H-1,2,4-三唑-1-基)噠嗪(0.15g, 0.32mmol)及間氯過苯甲酸(含量77%, 0.16g, 0.71mmol)加入至二氯甲烷(10mL)中,並進一步攪拌一整晚。將反應溶液注入飽和碳酸氫鈉水溶液中,並用乙酸乙酯進行萃取。用無水硫酸鎂使有機層乾燥之後,於減壓下蒸餾出溶劑,獲得4-(乙基磺醯基)-3-(4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基)-6(1H-1,2,4-三唑-1-基)噠嗪(0.17g, 產率:定量)。
1
H-NMR數據(300MHz, CDCl3
/TMS δ (ppm)):1.46(3H, t), 4.07(2H, q), 4.49(2H, t), 7.76(1H, s), 8.25(1H, s), 8.26(1H, s), 8.89(1H, s), 9.39(1H, s)
熔點 157-160℃
將根據前述實施例所製造的本發明化合物[I]的物性值(熔點、折射率及1
H-NMR光譜資料)表示於以下的表453~表480,包括前述實施例當中的值。另外,表中的化合物編號及符號係表示與上述相同的含意。
[表453]
[表454]
[表455]
[表456]
[表457]
[表458]
[表459]
[表460]
[表461]
[表462]
[表463]
[表464]
[表465]
[表466]
[表467]
[表468]
[表469]
[表470]
[表471]
[表472]
[表473]
[表474]
[表475]
[表476]
[表477]
[表478]
[表479]
[表480]
接著,將具體說明本發明的有害生物防治劑的製劑例,而其係使用了如上述方式所製造的本發明的唑衍生物或是其農藥上允許的鹽。惟,化合物、添加劑的種類以及混合比例並不限於僅此,可於寬廣的範圍中變更。此外,於以下說明中,「份」係指質量份。
[製劑例1] 乳劑
記載於表1~表480的化合物 10份
環己酮 30份
聚氧乙烯烷基芳基醚 11份
烷基苯磺酸鈣 4份
甲基萘 45份
將上述物質均勻溶解,製成乳劑。
[製劑例2] 可濕性粉劑
記載於表1~表480的化合物 10份
萘磺酸福爾馬林縮合物鈉鹽 0.5份
聚氧乙烯烷基芳基醚 0.5份
矽藻土 24份
黏土 65份
將以上物質均勻混合使其粉碎,製成可濕性粉劑。
[製劑例3] 粉劑
記載於表1~表480的化合物 2份
矽藻土 5份
黏土 93份
將以上物質均勻混合使其粉碎,製成粉劑。
[製劑例4] 顆粒劑
記載於表1~表480的化合物 5份
月桂醇硫酸酯鈉鹽 2份
木質素磺酸鈉 5份
羧甲基纖維素 2份
黏土 86份
將以上物質均勻混合,並使其粉碎。將相當於20份的水的量加入至此混合物中並捏合,使用擠出式造粒機加工成14~32目(mesh)的顆粒狀之後,使其乾燥製成粒劑。
[製劑例5] 流動劑
記載於表1~表480的化合物 20份
聚氧乙烯苯乙烯苯醚硫酸鹽 4份
乙二醇 7份
聚矽氧AF-118N(旭化成工業股份有限公司製) 0.02份
水 68.98份
將上述物質用高速攪拌器混合30分鐘之後,用濕式粉碎機使其粉碎,製成流動劑。
[製劑例6] 顆粒可濕性粉劑
記載於表1~表480的化合物 10份
木質素磺酸鈉 5份
聚氧乙烯烷基芳基醚 1份
聚羧酸鈉 3份
白碳 5份
預膠化澱粉 1份
碳酸鈣 65份
水 10份
將以上物質混合、捏合,並進行造粒。用流動層乾燥機使所獲得的粒狀物乾燥,並獲得顆粒可濕性粉劑。
接著,透過試驗例,針對本發明的有害生物防治劑所達到之功效進行說明。
[試驗例]
[試驗例1]小菜蛾殺蟲活性試驗
將根據製劑例2所調製的可濕性粉劑,作為有效成分用水稀釋為500ppm濃度。將白菜葉浸漬於其化學溶液中,風乾之後,放入塑料杯中。於其中放進10隻小菜蛾的二齡幼蟲並覆蓋。其後,將其放置於25℃的恆溫室,於6日之後調查死亡昆蟲數量,透過數1之算式來計算昆蟲死亡率。試驗為單輪制。
[數1]
基於此試驗顯示昆蟲死亡率為90%以上的化合物的化合物編號係如下所列。
A-0130、A-0145、A-0146、A-0147、A-0148、A-0149、A-0150、A-0169、A-0170、A-0171、A-0208、A-0209、A-0210、A-0763、A-0811、A-0892、A-0894、A-0895、A-0896、A-0897、A-1231、A-1232、A-1233、A-1438、A-1439、A-1440、A-1459、A-1460、A-1461、A-1465、A-1467、A-1488、A-1585、A-1586、A-1587、A-1593、A-1675、A-1676、A-1677、A-1678、A-1679、A-1680、A-1681、A-1682、A-1683、A-1684、A-1685、A-1686、A-1687、A-1688、A-1689、A-1690、A-1691、A-1692、A-1693、A-1696、A-1698、A-1735、A-1736、A-1737、A-1738、A-1739、A-1740、A-1750、A-1751、A-1752、A-1779、A-1827、A-1862、A-1993、A-1994、A-1995、A-1998、A-2000、A-2001、A-2022、A-2029、A-2030、A-2031、A-2043、A-2070、A-2106、A-2126、A-2127、A-2143、A-2144、A-2145、A-2147、A-2148、A-2218、A-2219、A-2220、A-2226、A-2243、A-2244、A-2266、A-2267、A-2268、A-2269、A-2270、A-2271、A-2272、A-2273、A-2274、A-2293、A-2295、A-2296、A-2298、A-2308、A-2309、A-2310、A-2314、A-2315、A-2316、A-2343、A-2344、A-2359、A-2360、A-2361、A-2386、A-2388、A-2389、A-2390、A-2391、A-2409、A-2454、A-2863、A-2864、A-2865、A-2875、A-2876、A-2877、A-2878、A-2879、A-2880、A-2926、A-2927、A-2928、A-2940、A-2943、A-3054、A-3060、A-3109、A-3111、A-3135、A-3136、A-3137、A-3138、A-3159、A-3370、A-3487、A-3589、A-3590、A-3591、A-3778、A-3779、A-3780、A-3790、A-3791、A-3792、A-3811、A-3812、A-3813、A-3814、A-3815、A-3816、A-3817、A-3819、A-3838、A-3839、A-3840、A-3886、A-3887、A-3888、A-3907、A-3909、A-3913、A-3915、A-3934、A-3935、A-3936、A-3970、A-3971、A-3972、A-3991、A-3997、A-3998、A-3999、A-4018、A-4019、A-4020、A-4024、A-4025、A-4026、A-4044、A-4132、A-4134、A-4366、A-4367、A-4368、A-4387、A-4388、A-4389、A-4393、A-4395、A-4414、A-4415、A-4416、A-4513、A-4514、A-4515、A-4537、A-4538、A-4539、A-4747、A-4772、A-5077、A-5079、A-5781、A-5896、A-5897、A-5941、A-5942、A-5943、A-5995、A-5996、A-5997、A-6004、A-6006、A-6556、A-6558、A-6988、A-6989、A-6990、A-6998、A-6999、A-7054、A-7055、A-7056、A-7063、A-7064、A-7065、B-0004、B-0005、B-0006、B-0553、B-0554、B-0555、B-0560、B-0561、B-0565、B-0566、B-0567、B-0595、B-0596、B-0597、B-0598、B-0599、B-0600、B-0763、B-0764、B-0765、B-0997、B-0998、B-0999、B-1642、B-1643、B-1644、B-1648、B-1649、B-1650、B-1669、B-1670、B-1671、B-1676、B-1696、B-1697、B-1698、B-1703、C-0190、C-0191、C-0192、D-0002、D-0446、D-0679、E-0150、E-0850、E-0976、E-1065、E-1068、E-1081、E-1094、E-1095、E-1096、E-1121、E-1123、F-0203、F-0204、F-0205、F-0301、F-0412、F-0541、F-0791、F-0793、F-0854、F-0855、F-0856、F-1076、F-1077、F-1078、F-1184、F-1185、F-1186、F-1401、F-1654、F-1771、F-1939、F-2047、F-2155、F-2263、F-2479、F-2695、F-2985、F-3003、F-3189、F-3198、G-0138、G-0139、H-0128、H-0129、H-0130、J-0115、J-0172、K-0063、K-0071、K-1403、K-1409、K-1410、K-1411、K-1418、K-1419、K-1420、K-1432、K-1478、K-1484、K-1485、K-1496、K-1505、K-1517、K-1544、K-1556、K-1571、K-1592、K-1662、K-1663、K-1664、K-1665、K-1666、K-1669、K-1670、K-1671、K-1705、K-1931、K-1932、K-1933、K-2055、K-2057、K-2111
[試驗例2]番茄夜蛾殺蟲活性試驗
將根據製劑例2所調製的可濕性粉劑,作為有效成分用水稀釋為500ppm濃度。將白菜葉浸漬於其化學溶液中,風乾之後,放入塑料杯中。於其中放進5隻番茄夜蛾的一齡幼蟲並覆蓋。其後,將其放置於25℃的恆溫室,於6日之後調查死亡昆蟲數量,透過數1之算式來計算昆蟲死亡率。試驗為二輪制。
基於此試驗顯示昆蟲死亡率為90%以上的化合物的化合物編號係如下所列。
A-0091、A-0092、A-0093、A-0129、A-0132、A-0145、A-0146、A-0147、A-0148、A-0149、A-0150、A-0208、A-0209、A-0210、A-0763、A-0808、A-0810、A-0811、A-0812、A-0860、A-0861、A-0892、A-0894、A-0895、A-0896、A-0897、A-1231、A-1232、A-1233、A-1438、A-1439、A-1440、A-1459、A-1460、A-1461、A-1465、A-1467、A-1486、A-1487、A-1488、A-1585、A-1586、A-1587、A-1593、A-1675、A-1676、A-1677、A-1678、A-1679、A-1680、A-1681、A-1682、A-1683、A-1684、A-1685、A-1686、A-1688、A-1689、A-1690、A-1691、A-1692、A-1693、A-1694、A-1695、A-1735、A-1736、A-1737、A-1738、A-1739、A-1740、A-1750、A-1751、A-1752、A-1779、A-1861、A-1862、A-1995、A-1996、A-1998、A-1999、A-2000、A-2001、A-2020、A-2021、A-2022、A-2029、A-2030、A-2031、A-2043、A-2070、A-2106、A-2125、A-2126、A-2127、A-2131、A-2143、A-2144、A-2145、A-2146、A-2147、A-2148、A-2218、A-2219、A-2220、A-2226、A-2266、A-2267、A-2268、A-2269、A-2271、A-2272、A-2273、A-2274、A-2293、A-2295、A-2296、A-2298、A-2308、A-2309、A-2310、A-2314、A-2315、A-2316、A-2343、A-2359、A-2360、A-2361、A-2386、A-2388、A-2389、A-2390、A-2391、A-2452、A-2453、A-2454、A-2506、A-2875、A-2876、A-2877、A-2879、A-2926、A-2927、A-2928、A-2932、A-2938、A-2939、A-2940、A-2944、A-2945、A-2946、A-2950、A-3059、A-3060、A-3109、A-3111、A-3127、A-3134、A-3135、A-3136、A-3138、A-3150、A-3156、A-3159、A-3186、A-3407、A-3487、A-3589、A-3590、A-3591、A-3778、A-3779、A-3780、A-3790、A-3791、A-3792、A-3811、A-3812、A-3813、A-3814、A-3815、A-3816、A-3817、A-3819、A-3838、A-3839、A-3840、A-3886、A-3887、A-3888、A-3907、A-3909、A-3913、A-3915、A-3934、A-3935、A-3936、A-3970、A-3971、A-3972、A-3991、A-3997、A-3998、A-3999、A-4018、A-4019、A-4020、A-4044、A-4366、A-4367、A-4368、A-4387、A-4388、A-4389、A-4393、A-4395、A-4414、A-4415、A-4416、A-4513、A-4514、A-4515、A-4537、A-4538、A-4539、A-4747、A-4748、A-4749、A-4771、A-4772、A-4773、A-5079、A-5545、A-5896、A-5897、A-5898、A-5917、A-5918、A-5919、A-5941、A-5942、A-5943、A-5996、A-6004、A-6005、A-6006、A-6556、A-6988、A-6989、A-6990、A-6997、A-6998、A-6999、A-7054、A-7055、A-7056、A-7063、A-7064、A-7065、B-0553、B-0554、B-0555、B-0559、B-0560、B-0561、B-0565、B-0566、B-0567、B-0597、B-0598、B-0599、B-0600、B-0763、B-0764、B-0765、B-0997、B-0998、B-0999、B-1642、B-1643、B-1644、B-1648、B-1650、B-1669、B-1670、B-1671、B-1676、B-1696、B-1697、B-1698、C-0190、C-0191、C-0192、D-0002、D-0035、D-0679、E-0150、E-0183、E-0850、E-0976、E-1065、E-1081、E-1094、E-1095、E-1096、E-1121、E-1122、F-0204、F-0299、F-0300、F-0301、F-0410、F-0411、F-0412、F-0540、F-0541、F-0793、F-0854、F-0855、F-0856、F-0965、F-0966、F-0967、F-1076、F-1077、F-1078、F-1184、F-1185、F-1186、F-1400、F-1401、F-1402、F-1654、F-1771、F-1939、F-2047、F-2155、F-2263、F-2587、F-2985、F-3003、F-3189、F-3198、G-0138、G-0140、K-0344、K-0345、K-0425、K-0426、K-0427、K-1403、K-1409、K-1410、K-1411、K-1418、K-1419、K-1420、K-1432、K-1478、K-1484、K-1485、K-1496、K-1517、K-1568、K-1661、K-1664、K-1665、K-1666、K-1669、K-1670、K-1671、K-1672、K-1703、K-1705、K-1932、K-1933、K-1951、K-2028、K-2029、K-2055、K-2057、K-2082、K-2083、K-2111
[試驗例3]褐飛蝨殺蟲活性試驗
將根據製劑例2所調製的可濕性粉劑,作為有效成分用水稀釋為500ppm濃度。將稻米之發芽稻穀浸漬於其化學溶液中,放入塑料杯中。於此塑料杯中放進10隻褐飛蝨的二齡幼蟲並覆蓋。其後,將其放置於25℃的恆溫室,於6日後調查死亡昆蟲數量,透過數1之算式來計算昆蟲死亡率。試驗為單輪制。
基於此試驗顯示昆蟲死亡率為90%以上的化合物的化合物編號係如下所列。
A-0091、A-0093、A-0127、A-0128、A-0129、A-0130、A-0131、A-0132、A-0145、A-0146、A-0147、A-0148、A-0149、A-0150、A-0169、A-0170、A-0171、A-0208、A-0209、A-0210、A-0895、A-0897、A-1087、A-1231、A-1438、A-1440、A-1459、A-1461、A-1465、A-1488、A-1585、A-1586、A-1587、A-1593、A-1675、A-1676、A-1677、A-1678、A-1680、A-1681、A-1682、A-1683、A-1684、A-1686、A-1687、A-1690、A-1693、A-1696、A-1735、A-1737、A-1738、A-1740、A-1752、A-1995、A-1998、A-2001、A-2031、A-2106、A-2145、A-2224、A-2242、A-2266、A-2268、A-2269、A-2271、A-2272、A-2293、A-2295、A-2298、A-2308、A-2314、A-2344、A-2865、A-2926、A-2932、A-2943、A-2944、A-3111、A-3133、A-3134、A-3136、A-3352、A-3406、A-3487、A-3589、A-3590、A-3591、A-3778、A-3792、A-3811、A-3812、A-3813、A-3814、A-3815、A-3816、A-3886、A-3887、A-3888、A-3901、A-3907、A-3909、A-3913、A-3915、A-3970、A-3971、A-3972、A-3991、A-4018、A-4020、A-4132、A-4368、A-4387、A-4389、A-4416、A-4513、A-4514、A-4515、A-4539、A-5311、A-5313、A-5942、A-6556、A-6592、A-6709、A-6988、A-6989、A-6990、A-6997、A-6998、A-6999、A-7054、A-7055、A-7063、B-0004、B-0553、B-0565、B-0595、B-0598、B-0600、B-0763、B-0764、B-0765、B-0997、B-0999、B-1642、B-1643、B-1648、B-1649、B-1650、B-1669、B-1675、B-1676、B-1677、B-1696、B-1697、B-1702、B-1703、B-1704、C-0187、C-0190、D-0629、D-0679、E-0150、E-0850、E-0976、E-1064、E-1070、E-1081、E-1094、F-0203、F-0241、F-0299、F-0410、F-0854、F-1076、F-1077、F-1078、F-1185、F-1654、F-1771、F-2047、F-2263、F-2985、G-0138、G-0139、H-0128、H-0129、H-0130、H-0413、H-0418、K-0062、K-0063、K-0064、K-0071、K-0072、K-0073、K-0080、K-0081、K-0344、K-0425、K-1042、K-1403、K-1409、K-1410、K-1411、K-1418、K-1419、K-1420、K-1430、K-1496、K-1505、K-1506、K-1517、K-1592、K-1661、K-1662、K-1664、K-1665、K-1670、K-1703、K-1754、K-1931、K-2028、K-2055、K-2057、K-2082、K-2083、K-2084、K-2111
[試驗例4]綿蚜殺蟲防治效果試驗
將根據製劑例2所調製的可濕性粉劑,作為有效成分用水稀釋為500ppm濃度。將事先接種過綿蚜幼蟲的黃瓜幼苗浸漬於此化學溶液中並風乾。將處理後的黃瓜幼苗放置於25℃的恆溫室,於3日之後計算存活的昆蟲數量,並透過數1之算式來計算昆蟲死亡率。試驗為單輪制。
基於此試驗顯示昆蟲死亡率為90%以上的化合物的化合物編號係如下所列。
A-0091、A-0127、A-0128、A-0129、A-0130、A-0131、A-0145、A-0146、A-0147、A-0148、A-0149、A-0150、A-0169、A-0170、A-0171、A-0208、A-0209、A-0210、A-0757、A-0763、A-0892、A-1440、A-1467、A-1486、A-1487、A-1488、A-1587、A-1593、A-1675、A-1676、A-1677、A-1678、A-1679、A-1680、A-1681、A-1683、A-1684、A-1686、A-1690、A-1692、A-1693、A-1698、A-1737、A-1738、A-1739、A-1740、A-1750、A-1751、A-1752、A-1779、A-1827、A-1996、A-1998、A-2001、A-2031、A-2106、A-2127、A-2131、A-2143、A-2144、A-2145、A-2218、A-2219、A-2220、A-2242、A-2243、A-2244、A-2268、A-2269、A-2271、A-2274、A-2295、A-2298、A-2343、A-2361、A-2454、A-2865、A-3057、A-3109、A-3111、A-3127、A-3133、A-3135、A-3138、A-3150、A-3159、A-3487、A-3589、A-3590、A-3591、A-3778、A-3779、A-3780、A-3792、A-3805、A-3813、A-3814、A-3815、A-3816、A-3819、A-3838、A-3839、A-3840、A-3887、A-3888、A-3901、A-3907、A-3909、A-3915、A-3934、A-3935、A-3936、A-3970、A-3971、A-3972、A-3991、A-3999、A-4018、A-4019、A-4020、A-4368、A-4395、A-4414、A-4415、A-4416、A-4515、A-4537、A-4538、A-4539、A-4772、A-5077、A-5781、A-5996、A-6988、A-6989、A-6990、A-6997、A-6998、A-6999、A-7054、A-7055、A-7063、A-7132、B-0004、B-0005、B-0006、B-0553、B-0567、B-0595、B-0596、B-0597、B-0598、B-0599、B-0600、B-0763、B-0764、B-0765、B-0997、B-0998、B-0999、E-0150、E-0850、E-1064、E-1065、E-1066、E-1070、E-1071、E-1081、E-1094、F-1078、F-1654、F-1771、F-1939、F-2155、F-2695、F-2985、F-3189、G-0138、G-0139、H-0128、H-0129、H-0130、H-0413、K-1042、K-1403、K-1409、K-1418、K-1430、K-1496、K-1505、K-1592、K-1932
[試驗例5] 娜美蜘蛛蟎防治效果試驗
將根據製劑例2所調製的可濕性粉劑,作為有效成分用水稀釋為500ppm濃度。將事先接種過35隻娜美蜘蛛蟎雌性成蟲的大豆幼苗浸漬於化學溶液中並風乾。將處理後的大豆幼苗放置於25℃的恆溫室,於13日之後調查雌性成蟲的存活昆蟲數量,並透過數2之算式來計算防治率。試驗為單輪制。
[數2]
基於此試驗顯示防治率為90%以上的化合物的化合物編號係如下所列。
A-0127、A-0130、A-0170、A-1438、A-1439、A-1586、A-2878、A-3135、A-3138、A-3590、A-3971、A-4018、A-4367、A-4514、A-6989、A-6990、A-6998、D-0629、E-1065、H-0128、H-0413、K-0072、K-0080、K-0081、K-0425、K-1430、K-1517、K-1969
[產業利用性]
本發明之通式[I]所示化合物或是其鹽係具有優異的有害生物防治作用,並且可用作農藥或殺蟲劑等之有效成分。此外,本發明之通式[II]所示化合物及本發明之通式[V]所示化合物係可用作通式[I]所示化合物的製造中間體。本發明在此等領域中具有產業利用性。
無。
無。
Claims (31)
- 一種化合物或是其鹽,係表示為: 通式[I] [式中, m及n係分別獨立且表示0、1或2的整數,且m及n的總和係在為0~2的整數之範圍內, R1 係表示:氫原子;氰基;或是未取代或以鹵素原子取代的C1 ~C7 醯基; R2 係表示:C1 ~C6 烷基;C1 ~C6 烷氧基C1 ~C6 烷基;C1 ~C6 鹵代烷基;C1 ~C6 烷氧基C1 ~C6 鹵代烷基;C1 ~C6 鹵代烷氧基C1 ~C6 烷基;C1 ~C6 鹵代烷氧基C1 ~C6 鹵代烷基;C3 ~C6 環烷基;C3 ~C6 鹵代環烷基;C3 ~C6 環烷基C1 ~C6 烷基;C3 ~C6 鹵代環烷基C1 ~C6 烷基;氰基C1 ~C6 烷基;未取代或以R11 任意取代的C7 ~C1 4 芳烷基;或未取代或以R11 任意取代的C6 ~C12 雜芳烷基; A3 , A4 , A5 , A6 , A7 , A8 及A9 分別獨立地表示氮原子,或是分別以R3 , R4 , R5 , R6 , R7 , R8 及R9 取代的碳原子; R3 , R4 , R5 , R6 , R7 , R8 及R9 分別獨立地表示:氫原子;鹵素原子;疊氮基;氰基;硝基;C1 ~C6 烷基、C1 ~C6 烷氧基C1 ~C6 烷基;C1 ~C6 鹵代烷氧基C1 ~C6 烷基;氰基C1 ~C6 烷基;C1 ~C6 鹵代烷基;C3 ~C6 環烷基;氰基C3 ~C6 環烷基;C3 ~C6 鹵代環烷基;C3 ~C6 環烷基C1 ~C6 烷基;C3 ~C6 鹵代環烷基C1 ~C6 烷基;C2 ~C6 烯基;C2 ~C6 鹵代烯基;C2 ~C6 炔基;C2 ~C6 鹵代炔基;C3 ~C6 環烷基C2 ~C6 炔基;未取代或以R11 任意取代的雜環基;未取代或以R11 任意取代的C6 ~C12 芳基;未取代或以R11 任意取代的C5 ~C12 雜芳基;未取代或以R11 任意取代的C7 ~C1 4 芳烷基;未取代或以R11 任意取代的C6 ~C12 雜芳烷基;羥基;C1 ~C6 烷氧基;C1 ~C6 鹵代烷氧基;氰基C1 ~C6 烷氧基;羥基C1 ~C6 烷氧基;C1 ~C6 鹵代烷氧基C1 ~C6 烷氧基;C1 ~C6 烷氧基C1 ~C6 鹵代烷氧基;C1 ~C6 鹵代烷氧基C1 ~C6 鹵代烷氧基;C3 ~C6 環烷氧基;C3 ~C6 環烷基C1 ~C6 烷氧基;C3 ~C6 鹵代環烷氧基;C3 ~C6 鹵代環烷基C1 ~C6 烷氧基;C1 ~C6 鹵代烷硫基C1 ~C6 烷氧基;C1 ~C6 鹵代烷基亞磺醯基C1 ~C6 烷氧基;C1 ~C6 鹵代烷基磺醯基C1 ~C6 烷氧基;未取代或以R11 任意取代的C7 ~C1 4 芳烷氧基;未取代或以R11 任意取代的C6 ~C12 雜芳烷氧基;未取代或以R11 任意取代的C6 ~C12 芳氧基;或未取代或以R11 任意取代的C5 ~C12 雜芳氧基;硫烷基;五鹵硫烷基;C1 ~C6 烷硫基;C1 ~C6 烷基亞磺醯基;C1 ~C6 烷基磺醯基;C1 ~C6 鹵代烷基硫磺基;C1 ~C6 鹵代烷基亞磺醯基;C1 ~C6 鹵代烷基磺醯基;C3 ~C6 環烷硫基;C3 ~C6 環烷基磺醯基;C3 ~C6 環烷基磺醯基;C3 ~C6 鹵代環烷基硫基;C3 ~C6 鹵代環烷基亞磺醯基;C3 ~C6 鹵代環烷基磺醯基,C3 ~C6 環烷基C1 ~C6 烷硫基;C3 ~C6 環烷基C1 ~C6 烷基亞磺醯基;C3 ~C6 環烷基C1 ~C6 烷基磺醯基;C3 ~C6 鹵代環烷基C1 ~C6 烷硫基;C3 ~C6 鹵代環烷基C1 ~C6 烷基亞磺醯基;C3 ~C6 鹵代環烷基C1 ~C6 烷基磺醯基;C6 ~C12 芳硫基;C6 ~C12 芳基亞磺醯基;C6 ~C12 芳基磺醯基;C5 ~C12 雜芳硫基;C5 ~C12 雜芳基亞磺醯基;C5 ~C12 雜芳基亞磺醯基;氨基;單(C1 ~C6 烷基)氨基;二(C1 ~C6 烷基)氨基;C1 ~C6 烷基羰基氨基;N-(C1 ~C6 烷基羰基)-N-(C1 ~C6 烷基)氨基;C1 〜C6 烷氧基羰基氨基;C1 ~C6 烷氧基羰基氨基;N-(C1 ~C6 烷氧基羰基羰基)-N-(C1 ~C6 烷基)氨基;N-(C1 ~C6 烷氧基羰基)-N-(C1 ~C6 烷基)氨基;氨基羰基氨基;N-(氨基羰基)-N-(C1 ~C6 烷基)氨基;N-(單(C1 ~C6 烷基)氨基羰基)氨基;N-(單(C1 ~C6 烷基)氨基羰基)-N-(C1 ~C6 烷基)氨基;N-(二(C1 ~C6 烷基)氨基羰基)氨基;N-(二(C1 ~C6 烷基)氨基羰基羰基)氨基;N-(二(C1 ~C6 烷基)氨基羰基)-N-(C1 ~C6 烷基)氨基;N-(二(C1 ~C6 烷基)氨基羰基羰基)-N-(C1 ~C6 烷基)氨基;氨基(硫代羰基)氨基;N-(二(C1 ~C6 烷基)氨基(硫代羰基))氨基;N-(二(C1 ~C6 烷基)氨基(硫代羰基))-N-(C1 ~C6 烷基)氨基;C1 ~C6 烷基磺醯基氨基;C1 ~C6 鹵代烷基磺醯基氨基;N-(C1 ~C6 烷基磺醯基)-N-(C1 ~C6 烷基)氨基;N-(C1 ~C6 鹵代烷基磺醯基)-N-(C1 ~C6 烷基)氨基;二(C1 ~C6 烷基磺醯基)氨基;二(C1 ~C6 鹵代烷基磺醯基)氨基;氨基磺醯基氨基;N-(氨基磺醯基)-N-(C1 ~C6 烷基)氨基;N-(單(C1 ~C6 烷基)氨基磺醯基)氨基;N-(單(C1 ~C6 烷基)氨基磺醯基)-N-(C1 ~C6 烷基)氨基;N-(二(C1 ~C6 烷基)氨基磺醯基)氨基;N-(二(C1 ~C6 烷基)氨基磺醯基)-N-(C1 ~C6 烷基)氨基;(二(C1 ~C6 烷基)亞硫烷基)氨基;C1 ~C7 醯基;C1 ~C7 鹵代醯基;羥基亞氨基C1 〜C6 烷基;羥基亞氨基(氨基)C1 〜C7 烷基;C1 〜C6 烷氧基亞氨基C1 〜C6 烷基;C1 〜C6 鹵代烷氧基亞氨基C1 〜C6 烷基;羧基;C1 〜C6 烷氧基羰基;氨基羰基;單(C1 ~C6 烷基)氨基羰基;二(C1 ~C6 烷基)氨基羰基;單(C1 ~C6 鹵代烷基)氨基羰基;單(C3 ~C6 環烷基)氨基羰基;(C1 〜C6 烷氧基)(C1 ~C6 烷基)氨基羰基;氨基硫代羰基;單(C1 ~C6 烷基)氨基硫代羰基;二(C1 ~C6 烷基)氨基硫代羰基;或N-(C1 ~C6 烷氧基)-N-(C1 ~C6 烷基)氨基羰基,且,R3 與R4 、R4 與R5 、或是R5 與R6 係可分別地形成具有將其鍵合的碳原子及3〜6元的碳環或是具有選自氧原子、硫原子、氮原子的1〜4個雜原子的3〜6元的雜環,該碳環及該雜環係可分別以鹵素原子;氰基;硝基;C1 〜C6 烷基;C1 〜C6 烷氧基;C1 〜C6 鹵代烷基;C1 〜C6 鹵代烷氧基;C3 ~C6 環烷基;C1 ~C6 烷氧基亞氨基C1 ~C6 烷基;C1 ~C6 鹵代烷氧基亞氨基C1 ~C6 烷基;羥基;氧代基;或硫氧基(thioxy)取代, R1 0 係表示:氫原子;C1 ~C12 烷基;C1 ~C6 烷氧基C1 ~C6 烷基;C1 ~C12 鹵代烷基;C1 ~C6 烷氧基C1 ~C6 鹵代烷基;C1 ~C6 鹵代烷氧基C1 ~C6 烷基;C1 ~C6 鹵代烷氧基C1 ~C6 鹵代烷基;C2 ~C6 烯基;C2 ~C6 鹵代烯基;C2 ~C6 炔基;C3 ~C6 環烷基C2 ~C6 炔基;C2 ~C6 鹵代炔基;C3 ~C6 環烷基;C3 ~C6 鹵代環烷基;C3 ~C6 環烷基C1 ~C6 烷基;C3 ~C6 鹵代環烷基C1 ~C6 烷基;C1 ~C6 烷硫基C1 ~C6 烷基;C1 ~C6 烷基亞磺醯基C1 ~C6 烷基;C1 ~C6 烷基磺醯基C1 ~C6 烷基;C1 ~C6 鹵代烷硫基C1 ~C6 烷基;C1 ~C6 鹵代烷基亞磺醯基C1 ~C6 烷基;C1 ~C6 鹵代烷基磺醯基C1 ~C6 烷基;C1 ~C6 烷基羰基C1 ~C6 烷基;C1 ~C6 鹵代烷基羰基C1 ~C6 烷基;C1 ~C6 烷氧基羰基C1 ~C6 烷基;氨基羰基C1 ~C6 烷基;單(C1 ~C6 烷基)氨基羰基C1 ~C6 烷基;單(C3 ~C6 環烷基)氨基羰基C1 ~C6 烷基;單(C1 ~C6 鹵代烷基)氨基羰基C1 ~C6 烷基;二(C1 ~C6 烷基)氨基羰基C1 ~C6 烷基;單(C1 ~C6 烷基羰基)氨基C1 ~C6 烷基;單(C1 ~C6 烷氧基羰基)氨基C1 ~C6 烷基;單(C1 ~C6 烷基磺醯基)氨基C1 ~C6 烷基;單(C1 〜C6 鹵代烷基磺醯基)氨基C1 ~C6 烷基;羥基C1 ~C6 烷基;羥基亞氨基C1 ~C6 烷基;C1 ~C6 烷氧基亞氨基C1 ~C6 烷基;C1 ~C6 鹵代烷氧基亞氨基C1 ~C6 烷基;氨基羰基;單(C1 ~C6 烷基)氨基羰基;單(C3 ~C6 環烷基)氨基羰基;單(C1 ~C6 鹵代烷基)氨基羰基;二(C3 ~C6 環烷基)氨基羰基; (C1 ~C6 鹵代烷基)(單(C1 ~C6 鹵代烷基)氨基羰基)氨基羰基;(C1 ~C6 鹵代烷基)(C1 ~C6 鹵代烷基亞氨基C1 ~C6 鹵代烷基)氨基羰基;C1 ~C7 醯基;C1 ~C7 鹵醯基;未取代或是以R11 任意取代的C6 ~C12 芳基羰基;C1 ~C6 烷基磺醯基;C1 ~C6 鹵代烷基磺醯基;未取代或以R11 任意取代C7 ~C1 4 的芳烷基;未取代或以R11 任意取代的C6 ~C12 雜芳烷基;未取代或以R11 任意取代的C6 ~C12 芳基;或是未取代或以R11 任意取代的C5 ~C12 雜芳基, R11 係表示:鹵素原子;疊氮基;氰基;硝基;C1 ~C6 烷基;C1 ~C6 鹵代烷基;C1 ~C6 烷氧基;C1 ~C6 鹵代烷氧基;C3 ~C6 環烷基;五鹵硫烷基;C1 ~C6 烷硫基;C1 ~C6 烷基亞磺醯基;C1 ~C6 烷基磺醯基;C1 ~C6 鹵代烷硫基;C1 ~C6 鹵代烷基亞磺醯基;C1 ~C6 鹵代烷基磺醯基;氨基;單(C1 ~C6 烷基)氨基;或是二(C1 ~C6 烷基)氨基]。
- 如請求項1所述之化合物或是其鹽,其中,A7 係表示氮原子,A8 及A9 係分別表示以R8 及R9 取代的碳原子。
- 如請求項1所述之化合物或是其鹽,其中,A7 係表示氮原子,且A3 , A4 , A5 , A6 , A8 及A9 係分別表示以R3 , R4 , R5 , R6 , R8 及R9 取代的碳原子。
- 如請求項3所述之化合物或是其鹽,其中,R3 , R4 , R5 , R6 , R8 及R9 係分別獨立且表示氫原子、鹵素原子、C1 ~C6 鹵代烷基、C1 ~C6 鹵代烷氧基、或未取代或以R11 任意取代的雜環基。
- 如請求項1~4中任一項所述之化合物或是其鹽,其中,R2 係表示C1 ~C6 烷基。
- 如請求項1~5中任一項所述之化合物或是其鹽,其中,R1 0 係表示C1 ~C12 鹵代烷基。
- 如請求項7所述之化合物或是其鹽,其中,n為2,R4 為C1 ~C6 鹵代烷基、C1 ~C6 鹵代烷氧基、或是未取代或以R11 任意取代的雜環基,R8 及R9 係分別獨立為氫原子或鹵素原子,R1 0 為C1 ~C6 鹵代烷基。
- 一種農藥組合物,其中含有如請求項1~18中任一項所述之化合物或是其農業上可允許的鹽以作為有效成分。
- 如請求項19所述之農藥組合物,其中,農藥組合物還含有表面活性劑。
- 一種有害生物防治劑,其中含有如請求項1~18中任一項所述之化合物或是其鹽,以作為活性成分。
- 如請求項21所述之有害生物防治劑,其中,有害生物防治劑係為殺蟲劑、殺線蟲劑或殺蟎劑。
- 如請求項22所述之有害生物防治劑,其對於用於栽培農園藝用植物的稻田、田地、草皮、果園、非農耕地、溫室、育苗設施、植物工廠中的有害生物具有防治效力。
- 如請求項23所述之有害生物防治劑,其中,所述農園藝用植物係為透過育種方法或基因重組技術而被賦予抗性的植物。
- 一種有害生物的防治方法,其係使用如請求項1~18中任一項所述之化合物或是其鹽的有效成分量。
- 一種有害生物的防治方法,其係使含有如請求項1~18中任一項所述之化合物或是其鹽為有效成分的農藥組合物,同時地或是分開地,對於使農園藝用作物;或是欲使生長或已生長著農園藝用作物的場所,產生作用。
- 如請求項25或26所述之有害生物的防治方法,其中,施用有害生物防治劑的場所係為稻田、田地、草皮、果園、非農耕地、溫室、育苗設施、植物工廠。
- 如請求項25~27中任一項所述之有害生物的防治方法,其中,使用如請求項1~18中任一項所述之化合物或是其鹽,以作為殺蟲劑、殺線蟲劑或殺蟎劑使用。
- 一種有害生物防治劑的使用方法,其係將如請求項21~24中任一項所述之有害生物防治劑,使用於防治農園藝用作物的有害生物。
- 一種化合物或是其鹽,其中,於所述通式[I]當中,R1 0 為氫原子的化合物或是其鹽。
- 一種化合物的製造方法,其特徵在於,所述化合物係為如請求項1所述之通式[I]所表示的化合物,且係以如請求項30所述之化合物或是其鹽為原料。
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JP2022185597A (ja) | 2022-12-15 |
AR120307A1 (es) | 2022-02-09 |
WO2021085370A1 (ja) | 2021-05-06 |
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