TW202304904A - 雜環化合物及其用途 - Google Patents
雜環化合物及其用途 Download PDFInfo
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- TW202304904A TW202304904A TW111112421A TW111112421A TW202304904A TW 202304904 A TW202304904 A TW 202304904A TW 111112421 A TW111112421 A TW 111112421A TW 111112421 A TW111112421 A TW 111112421A TW 202304904 A TW202304904 A TW 202304904A
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- Prior art keywords
- alkyl
- group
- compound
- alkoxy
- cycloalkyl
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 16
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 113
- 150000003839 salts Chemical class 0.000 claims abstract description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 66
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 53
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 35
- 239000004480 active ingredient Substances 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 31
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 125000005843 halogen group Chemical group 0.000 claims abstract description 20
- 230000000694 effects Effects 0.000 claims abstract description 12
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 5
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 856
- 150000001875 compounds Chemical class 0.000 claims description 234
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 40
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 239000002917 insecticide Substances 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 10
- 230000000895 acaricidal effect Effects 0.000 claims description 10
- 239000005645 nematicide Substances 0.000 claims description 10
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 9
- 239000000642 acaricide Substances 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 9
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 230000001069 nematicidal effect Effects 0.000 claims description 7
- 108090000623 proteins and genes Proteins 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 238000009395 breeding Methods 0.000 claims description 5
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000002420 orchard Substances 0.000 claims description 4
- 238000005215 recombination Methods 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000005252 haloacyl group Chemical group 0.000 claims description 3
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 3
- 230000006798 recombination Effects 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 24
- 239000000543 intermediate Substances 0.000 abstract description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 133
- 239000002585 base Substances 0.000 description 46
- 229910052751 metal Inorganic materials 0.000 description 46
- 239000002184 metal Substances 0.000 description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000002904 solvent Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- 239000000126 substance Substances 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 241000578422 Graphosoma lineatum Species 0.000 description 22
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000003446 ligand Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 18
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 238000009472 formulation Methods 0.000 description 17
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 241000254173 Coleoptera Species 0.000 description 15
- 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 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 159000000000 sodium salts Chemical class 0.000 description 15
- 229940086542 triethylamine Drugs 0.000 description 15
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 14
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 14
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 230000000749 insecticidal effect Effects 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 125000002950 monocyclic group Chemical group 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 241000239290 Araneae Species 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 150000004702 methyl esters Chemical class 0.000 description 10
- 239000007800 oxidant agent Substances 0.000 description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- 241000258937 Hemiptera Species 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 9
- 239000004927 clay Substances 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 150000008282 halocarbons Chemical class 0.000 description 9
- 125000005347 halocycloalkyl group Chemical group 0.000 description 9
- 239000012046 mixed solvent Substances 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- 150000007530 organic bases Chemical class 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 9
- 235000019798 tripotassium phosphate Nutrition 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 8
- 241000193388 Bacillus thuringiensis Species 0.000 description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Substances IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
- 229910000024 caesium carbonate Inorganic materials 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 229910052791 calcium Inorganic materials 0.000 description 8
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 8
- 229960001231 choline Drugs 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000002798 polar solvent Substances 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 229960004418 trolamine Drugs 0.000 description 8
- 239000004563 wettable powder Substances 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 7
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 7
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 244000269722 Thea sinensis Species 0.000 description 7
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 7
- 150000008041 alkali metal carbonates Chemical class 0.000 description 7
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 7
- 229940097012 bacillus thuringiensis Drugs 0.000 description 7
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 7
- 239000000920 calcium hydroxide Substances 0.000 description 7
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 7
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 150000007529 inorganic bases Chemical class 0.000 description 7
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 7
- 229910052808 lithium carbonate Inorganic materials 0.000 description 7
- 229910000103 lithium hydride Inorganic materials 0.000 description 7
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 7
- 239000000347 magnesium hydroxide Substances 0.000 description 7
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- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- DBHVHTPMRCXCIY-UHFFFAOYSA-N tyclopyrazoflor Chemical compound N1=C(Cl)C(N(C(=O)CCSCCC(F)(F)F)CC)=CN1C1=CC=CN=C1 DBHVHTPMRCXCIY-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004549 water soluble granule Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Insects & Arthropods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
本發明提供具有優異之害蟲防治效果的雜環化合物或其鹽、包含其作為活性成分之害蟲防治劑以及其之製造中間體。
本發明提供通式[I]代表的雜環化合物
(其中,R
1代表氫原子、氰基、或未經取代或經鹵原子取代之C
1-C
7醯基,R
2代表C
1-C
6烷基等,A
1及A
2各自獨立地代表氮原子、CH或一鍵,W
1或W
2代表氮原子,而另一者代表碳原子,A
3、A
4、A
5、A
6、A
7、A
8及A
9各獨立地代表氮原子或分別經R
3、R
4、R
5、R
6、R
7、R
8及R
9取代之碳原子,R
3、R
4、R
5、R
6、R
7、R
8及R
9各代表氫原子、C
1-C
6鹵烷基等,R
10代表氫原子、C
1-C
12烷基、C
1-C
6烷氧基C
1-C
6烷基、C
1-C
12鹵烷基等,且R
11代表鹵原子、疊氮基、氰基等)或其農藥可接受的鹽,及提供害蟲防治劑,其特徵在於含有其作為活性成分。
Description
本發明係關於含有新穎雜環化合物或其鹽、衍生物或其鹽作為活性成分之害蟲防治劑,及生產其中間體。
專利文獻1敘述具有殺蟲活性之化合物。
專利文獻2敘述具有殺蟲活性且與單環基團耦合之化合物。
專利文獻3敘述具有殺蟲活性且藉由氮-碳鍵與單環基團耦合之化合物。
專利文獻4敘述具有殺蟲活性之二芳基唑化合物。
專利文獻5敘述具有殺蟲活性之烷氧基吡唑化合物。
專利文獻6敘述在與藉由氮-碳鍵結合的含氮五員環相鄰的位置上結合含硫取代基的稠環化合物。然而,並沒有關於殺蟲活性的敘述。
在上述專利文獻中,並未揭示本發明之雜環化合物。
先前技術文獻 專利文獻1. 國際專利公開號2017/061497
2. 國際專利公開號2018/052119
3. 國際專利公開號2019/124548
4. 國際專利公開號2016/204270
5. 日本專利公開號2021-024859
6. 國際專利公開號03/048081
發明欲解決之問題預期用於有用作物的害蟲防治劑在施用於土壤或樹葉時以低劑量表現出足夠的害蟲防治效果。此外,由於對化學物質的安全性及其對環境影響的要求越來越高,因此期望開發更安全的害蟲防治劑。此外,近年來,由於長期使用殺蟲劑、殺蟎劑及殺線蟲劑等害蟲防治劑,出現了對害蟲防治劑產生抗性的害蟲。因此,變得難以完全控制害蟲。此外,使用對人和動物具有高毒性的害蟲防治劑對於工作者安全等方面也是一項問題。
本發明的課題在於解決現有的害蟲防治劑在這種情況下存在的上述問題,進而提供具有優異的安全性、防治效果、殘留效果等的害蟲防治劑以及用於該目的的新穎化合物。
解決問題的手段為了開發具有上述較佳特性的害蟲防治劑,本發明人合成了各種雜環化合物並深入研究它們的生理活性。結果發現,由下述通式[I]表示的雜環化合物(以下,亦稱為本發明化合物)對各種害蟲具有優異的防治效果。本發明人持續進一步研究並完成了本發明。
亦即,本發明係關於以下態樣。
(1) 通式[I]表示之化合物或其鹽,其中,
m及n各獨立地代表0、1或2之整數,且其總合為0至2之整數,
R
1代表氫原子、氰基或未經取代或經鹵原子取代之C
1-C
7醯基,
R
2代表C
1-C
6烷基、C
1-C
6烷氧基C
1-C
6烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基C
1-C
6鹵烷基、C
1-C
6鹵烷氧基C
1-C
6烷基、C
1-C
6鹵烷氧基C
1-C
6鹵烷基、C
3-C
6環烷基、C
3-C
6鹵環烷基、C
3-C
6環烷基C
1-C
6烷基、C
3-C
6鹵環烷基C
1-C
6烷基、氰基C
1-C
6烷基、氰基C
3-C
6環烷基、未經取代或可選擇地經R
11取代之C
7-C
14芳烷基、或未經取代或可選擇地經R
11取代之C
6-C
14雜芳烷基,
W
1代表氮原子,
W
2代表碳原子,或
W
1代表碳原子,
W
2代表氮原子,
A
1代表氮原子、經R
a取代之碳原子、或一鍵,
A
2代表氮原子、經R
b取代之碳原子、或一鍵,
A
3代表氮原子、經R
3取代之碳原子、或一鍵,
A
1、A
2或A
3之任一者為一鍵,
A
4、A
5、A
6、A
7、A
8及A
9各獨立地代表氮原子、或分別經R
4、R
5、R
6、R
7、R
8及R
9取代之碳原子,
R
a、R
b、R
3、R
4、R
5、R
6、R
7、R
8及R
9各獨立地代表氫原子、鹵原子、疊氮基、氰基、硝基、C
1-C
6烷基、氰基C
1-C
6烷基、羥基C
1-C
6烷基、C
1-C
6鹵烷基、C
2-C
6烯基、C
2-C
6炔基、C
3-C
6環烷基、氰基C
3-C
6環烷基、羥基C
3-C
6環烷基、C
3-C
6鹵環烷基、C
3-C
6環烯基、C
3-C
6環烷基C
1-C
6烷基、C
3-C
6鹵環烷基C
1-C
6烷基、C
3-C
6環烷基C
2-C
6烯基、C
3-C
6環烷基C
2-C
6炔基、未經取代或可選擇地經R
11取代之雜環基、未經取代或可選擇地經R
11取代之C
6-C
12芳基、未經取代或可選擇地經R
11取代之C
5-C
12雜芳基、未經取代或可選擇地經R
11取代之C
7-C
14芳烷基、未經取代或可選擇地經R
11取代之C
6-C
14雜芳烷基、羥基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、氰基C
1-C
6烷氧基、羥基C
1-C
6烷氧基、C
1-C
6鹵烷氧基C
1-C
6烷氧基、C
1-C
6烷氧基C
1-C
6鹵烷氧基、C
1-C
6鹵烷氧基C
1-C
6鹵烷氧基、C
3-C
6環烷氧基、C
3-C
6環烷基C
1-C
6烷氧基、C
3-C
6鹵環烷氧基、氰基C
3-C
6環烷氧基、C
3-C
6鹵環烷基C
1-C
6烷氧基、(氰基C
3-C
6環烷基)C
1-C
6烷氧基、C
1-C
6鹵烷基硫基C
1-C
6烷氧基、C
1-C
6鹵烷基亞磺醯基C
1-C
6烷氧基、C
1-C
6鹵烷基磺醯基C
1-C
6烷氧基、未經取代或可選擇地經R
11取代之C
7-C
14芳烷氧基、未經取代或可選擇地經R
11取代之C
6-C
14雜芳烷氧基、未經取代或可選擇地經R
11取代之C
6-C
12芳氧基、未經取代或可選擇地經R
11取代之C
5-C
12雜芳氧基、氫硫基、五鹵氫硫基、C
1-C
6烷基硫基、C
1-C
6烷基亞磺醯基、C
1-C
6烷基磺醯基、C
1-C
6鹵烷基硫基、C
1-C
6鹵烷基亞磺醯基、C
1-C
6鹵烷基磺醯基、C
3-C
6環烷基硫基、C
3-C
6環烷基亞磺醯基、C
3-C
6環烷基磺醯基、C
3-C
6鹵環烷基硫基、C
3-C
6鹵環烷基亞磺醯基、C
3-C
6鹵環烷基磺醯基、C
3-C
6環烷基C
1-C
6烷基硫基、C
3-C
6環烷基C
1-C
6烷基亞磺醯基、C
3-C
6環烷基C
1-C
6烷基磺醯基、C
3-C
6鹵環烷基C
1-C
6烷基硫基、C
3-C
6鹵環烷基C
1-C
6烷基亞磺醯基、C
3-C
6鹵環烷基C
1-C
6烷基磺醯基、基團-S (R
12) = NH、基團-S (R
12) = N-C≡N、基團-S (R
12) = N-C (= O) R
13、基團-S (R
12) (= O) = NH、基團-S (R
12) (= O) = N-C≡N、基團-S (R
12) (= O) = N-C (= O) R
13、C
6-C
12芳基硫基、C
6-C
12芳基亞磺醯基、C
6-C
12芳基磺醯基、C
5-C
12雜芳基硫基、C
5-C
12雜芳基亞磺醯基、C
5-C1
2雜芳基磺醯基、胺基、單(C
1-C
6烷基)胺基、二(C
1-C
6烷基)胺基、(二(C
1-C
6烷基)亞磺醯亞基)胺基、二(C
1-C
6烷基)磷醯基、C
1-C
7醯基、C
1-C
7鹵醯基、羥基亞胺基C
1-C
6烷基、羥基亞胺基(胺基)C
1-C
7烷基、C
1-C
6烷氧基亞胺基C
1-C
6烷基、C
1-C
6鹵烷氧基亞胺基C
1-C
6烷基、羧基、C
1-C
6烷氧基羰基、胺基羰基、單(C
1-C
6烷基)胺基羰基、二(C
1-C
6烷基)胺基羰基、單(C
1-C
6鹵烷基)胺基羰基、單(C
3-C
6環烷基)胺基羰基、單(氰基C
3-C
6環烷基)胺基羰基、單(C
1-C
6烷氧基亞胺基C
1-C
6烷基)胺基羰基、二(C
1-C
6烷基)胺基亞甲基胺基羰基、胺基硫羰基、單(C
1-C
6烷基)胺基硫羰基、二(C
1-C
6烷基)胺基硫羰基、或N-(C
1-C
6烷氧基)-N-(C
1-C
6烷基)胺基羰基,
R
10代表氫原子、C
1-C
12烷基、C
1-C
6烷氧基C
1-C
6烷基、C
1-C
12鹵烷基、C
1-C
6烷氧基C
1-C
6鹵烷基、C
1-C
6鹵烷氧基C
1-C
6烷基、C
1-C
6鹵烷氧基C
1-C
6鹵烷基、C
2-C
6烯基、C
2-C
6鹵烯基、C
2-C
6炔基、C
3-C
6環烷基C
2-C
6炔基、C
2-C
6鹵炔基、C
3-C
6環烷基、C
3-C
6鹵環烷基、C
3-C
6環烷基C
1-C
6烷基、C
3-C
6鹵環烷基C
1-C
6烷基、未經取代或可選擇地經R
11取代之雜環基C
1-C
6烷基、未經取代或可選擇地經R
11取代之C
7-C
14芳烷基、未經取代或可選擇地經R
11取代之C
6-C
14雜芳烷基、未經取代或可選擇地經R
11取代之C
6-C
12芳基、或未經取代或可選擇地經R
11取代之C
5-C
12雜芳基,及
R
11代表鹵原子、疊氮基、氰基、硝基、C
1-C
6烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、C
3-C
6環烷基、五鹵氫硫基、C
1-C
6烷基硫基、C
1-C
6烷基亞磺醯基、C
1-C
6烷基磺醯基、C
1-C
6鹵烷基硫基、C
1-C
6鹵烷基亞磺醯基、C
1-C
6鹵烷基磺醯基、胺基、單(C
1-C
6烷基)胺基,或二(C
1-C
6烷基)胺基,
R
12及R
13獨立地代表C
1-C
6烷基、C
1-C
6烷氧基C
1-C
6烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基C
1-C
6鹵烷基、C
1-C
6鹵烷氧基C
1-C
6烷基、C
1-C
6鹵烷氧基C
1-C
6鹵烷基、C
3-C
6環烷基、C
3-C
6鹵環烷基、C
3-C
6環烷基C
1-C
6烷基、C
3-C
6鹵環烷基C
1-C
6烷基、氰基C
1-C
6烷基、未經取代或可選擇地經R
11取代之C
7-C
14芳烷基、或未經取代或可選擇地經R
11取代之C
6-C
14雜芳烷基。(2)根據上述(1)之化合物或其鹽,其中A
7代表氮原子,且A
8及A
9各代表分別經R
8及R
9取代之碳原子。
(3) 根據上述(1)之化合物或其鹽,其中A
1代表一鍵,
且A
2及A
7各代表氮原子,
W
1代表氮原子,
W
2代表碳原子,
A
3、A
4、A
5、A
6、A
8及A
9各代表分別經R
3、R
4、R
5、R
6、R
8及R
9取代之碳原子。
(4) 根據上述(3)之化合物或其鹽,其中R
3、R
4、R
5、R
6、R
8及R
9各獨立地代表氫原子、鹵原子、C
1-C
6烷基、C
1-C
6鹵烷基、氰基C
3-C
6環烷基、C
1-C
6鹵烷氧基或氰基C
1-C
6烷氧基。
(5) 根據上述(1)至(4)中任一項之化合物或其鹽,其中R
2代表C
1-C
6烷基。
(6) 根據上述(1)至(5)中任一項之化合物或其鹽,其中R
10代表C
1-C
12鹵烷基。
(7) 根據上述(1)之化合物或其鹽,其中該通式[I]代表之化合物為通式[Ia]代表之化合物,其中
A
2、A
3、A
4、A
5、A
6、A
7、A
8、A
9、m、n、R
1、R
2及R
10具有如上述(1)中相同之含意。
(8) 根據上述(1)之化合物或其鹽,其中該通式[I]代表之化合物為通式[A]代表之化合物,其中
n、R
3、R
4、R
5、R
6及R
10具有如上述(1)中相同之含意。
(9) 根據上述(8)之化合物或其鹽,其中n為2,R
3、R
5及R
6各為氫原子,R
4為C
1-C
6鹵烷基、氰基C
3-C
6環烷基、C
1-C
6鹵烷氧基、或氰基C
1-C
6烷氧基,且R
10為C
1-C
12鹵烷基。
(10) 根據上述(1)之化合物或其鹽,其中該通式[I]代表之化合物為通式[B]代表之化合物,其中
R
2、R
4、R
5及R
10具有如上述(1)中相同之含意。
(11) 根據上述(1)之化合物或其鹽,其中該通式[I]代表之化合物為通式[C]代表之化合物,其中
m、n、R
1、R
4、R
5及R
10具有如上述(1)中相同之含意。
(12) 根據上述(1)之化合物或其鹽,其中該通式[I]代表之化合物為通式[D]代表之化合物,其中
A
2、A
3、A
4、A
5、A
6及R
10具有如上述(1)中相同之含意。
(13) 根據上述(12)之化合物或其鹽,其中A
2代表經R
b取代之氮原子或碳原子,A
3代表經R
3取代之氮原子或碳原子,且A
4、A
5及A
6各獨立地代表分別經R
4、R
5及R
6取代之氮原子或碳原子。
(14) 一種殺蟲劑組成物,其包含根據上述(1)至(13)之化合物或其鹽作為活性成分。
(15) 根據上述(14)之殺蟲劑組成物,其中該殺蟲劑組成物進一步包含表面活性劑。
(16) 一種害蟲防治劑,其包含根據上述(1)至(13)之化合物或其鹽作為活性成分。
(17) 根據上述(16)之害蟲防治劑,其中該害蟲防治劑為殺蟲劑、殺線蟲劑或殺蟎劑。
(18) 根據上述(17)之害蟲防治劑,其對於在水田、農地、草坪、果園、非農用地、溫室、苗圃設施、種植農業及園藝植物的植物工廠具有防治害蟲效果。
(19) 根據上述(18)之害蟲防治劑,其中該農業及園藝植物是藉由育種方法或基因重組技術產生抗性的植物。
(20) 一種防治害蟲之方法,其使用有效量之根據上述(1)至(13)之化合物或其鹽。
(21) 一種防治害蟲之方法,其藉由使包含上述(1)至(13)之化合物或其鹽作為活性成分的殺蟲劑組成物以同時或分次作用於欲生長或正在生長農作物或園藝作物的場所。
(22) 根據上述(20)或(21)之防治害蟲之方法,其中該害蟲防治劑施用的場所為水田、農地、草坪、果園、非農用地、溫室、苗圃設施或植物工廠。
(23) 根據上述(20)至(22)之防治害蟲之方法,其中該根據上述(1)至(13)之化合物或其鹽用作殺蟲劑、殺線蟲劑或殺蟎劑。
(24) 一種根據上述(16)至(19)之害蟲防治劑用於在農作物或園藝作物上防治害蟲的用途。
(25) 根據上述(1)之通式[I]代表之化合物或其鹽,其中在通式[I]中之R
10為氫原子。
(26) 一種製造根據上述(1)之通式[I]代表的化合物之方法,其包含使用根據上述(25)之化合物或其鹽作為中間體。
本發明之功效含有本發明化合物的害蟲防治劑可對於廣範圍之害蟲呈現優異的防治效果,諸如對於半翅目害蟲、鱗翅目害蟲、鞘翅目害蟲、雙翅目害蟲、膜翅目害蟲、直翅目害蟲、等翅目害蟲、櫻翅目害蟲、蟎類、 和植物寄生性線蟲,且亦可防治已獲得殺蟲劑抗藥性之害蟲。
將描述本文所描述之符號及術語。
在本發明中,「害蟲防治劑」亦指用於農業或園藝領域及諸如牲畜及寵物之動物的家庭及流行病預防的殺蟲劑、殺線蟲劑或殺蟎劑。
在本發明中,「鹵原子」係指氟原子、氯原子、溴原子及碘原子。
在本發明中,諸如「C
1-C
6」之符號表明元素符號後面的數字代表碳原子數。例如,在這種情況下,碳原子數可在1至6的範圍內。
在本發明中,「C
1-C
2烷基」係指具有1至2個碳原子的直鏈烷基,除非另有指明。例如,可述及甲基及乙基等。
在本發明中,「C
1-C
6烷基」係指具有1至6個碳原子的直鏈或支鏈烷基,除非另有指明。例如,除了上述「C
1-C
2烷基」中的實例,可述及正丙基、異丙基、正丁基、二級丁基、異丁基、三級丁基、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、1-乙基-2-甲基丙基等。
在本發明中,「C
1-C
12烷基」係指具有1至12個碳原子的直鏈或支鏈烷基,除非另有指明。例如,除了上述「C
1-C
6烷基」中的實例,可述及庚基、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、十一基、1-甲基癸基、異十一基、十二基、1-甲基十一基、異十二基等。
在本發明中,「C
1-C
6鹵烷基」係指具有經1至13個相同或不同之鹵原子取代的1至6個碳原子的直鏈或支鏈烷基,除非另有指明。例如,可述及氟甲基、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-2-基、2-氟丙-2-基、1,1-二氟丙-2-基、1,2-二氟丙-2-基、1,3-二氟丙-2-基、1,2,3-三氟丙-2-基、1,1,3,3-四氟丙-2-基、1,1,1,3,3,3-六氟丙-2-基、七氟丙-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-2-基、2-氯丙-2-基、1,1-二氯丙-2-基、1,2-二氯丙-2-基、1,3-二氯丙-2-基、1,2,3-三氯丙-2-基、1,1,3,3-四氯丙-2-基、1,1,1,3,3,3-六氯丙-2-基、七氯丙-2-基、1-溴丙基、2-溴丙基、3-溴丙基、1-溴丙-2-基、2-溴丙-2-基、1-碘丙基、2-碘丙基、3-碘丙基、1-碘丙-2-基、2-碘丙-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-2-基、4,4,4-三氟丁-2-基、3,3,4,4,4-五氟丁-2-基、九氟丁-2-基、1,1,1,3,3,3-六氟-2-(三氟甲基)丙-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-2-基、4,4,4-三氯丁-2-基、九氯丁-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、3,3,4,4,5,5,5-七氟戊基、2,2,3,3,4,4,5,5,5-九氟戊基、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6-碘己基等。
在本發明中,「C
1-C
12鹵烷基」係指具有經1至25個相同或不同之鹵原子取代的1至12個碳原子的直鏈或支鏈烷基,除非另有指明。例如,除了上述「C
1-C
6鹵烷基」中的實例,可述及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-全氟癸基或全氟癸基等。
在本發明中,「C
3-C
6環烷基」係指具有3至6個碳原子的環烷基,除非另有指明。例如,可述及環丙基、環丁基、環戊基及環己基等。
在本發明中,「C
3-C
6鹵環烷基」係指具有經1至11個相同或不同之鹵原子取代的3至6個碳原子的環烷基,除非另有指明。例如,可述及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、4,4-二碘環己基或全氟環己基等。
在本發明中,「C
2-C
6烯基」係指具有2至6個碳原子的直鏈或支鏈烯基,除非另有指明。例如,可述及乙烯基、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、2,4-己二烯基或3,3-二甲基-1-丁烯基等。
在本發明中,「C
2-C
6鹵烯基」係指具有經1至11個相同或不同之鹵原子取代的2至6個碳原子的直鏈或支鏈烯基,除非另有指明。例如,可述及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-丙烯基、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-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5,5,5-三氯-4-甲基-3-戊烯基等。
在本發明中,「C
3-C
6環烯基」係指具有3至6個碳原子的環烯基,除非另有指明。例如,可述及1-環丙烯-1-基、1-環丁烯-1-基、1-環戊烯-1-基或1-環己烯-1-基等。
在本發明中,「C
2-C
6炔基」係指具有2至6個碳原子的直鏈或支鏈炔基,除非另有指明。例如,可述及乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、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2,2-二甲基-3-丁炔基或3,3-二甲基-1-丁炔基等。
在本發明中,「C
2-C
6鹵炔基」係指具有經1至9個相同或不同之鹵原子取代的2至6個碳原子的直鏈或支鏈炔基,除非另有指明。例如,可述及氟乙炔基、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-己炔基、5-氟-3-甲基-4-戊炔基或5-氯-3-甲基-4-戊炔基等。
在本發明中,「C
3-C
6環烷基C
2-C
6炔基」意指其中C
2-C
6炔基的任何位置被C
3-C
6環烷基取代的基團,其中該環烷基部分及該炔基部分具有上述含意,除非另有指明。例如,可述及環丙基乙炔基、環丁基乙炔基、環戊基乙炔基、環己基乙炔基、3-環丙基-1-丙炔基、1-環丙基-2-丙炔基、3-環丙基-2-丙炔基、3-環丙基-1,1-二甲基-2-丙炔基、4-環丙基-1,1-二甲基-2-丁炔基等。
在本發明中,「C
1-C
6烷氧基」意指(C
1-C
6烷基)-O-基團,其中該烷基部分具有上述含意,除非另有指明。例如,可述及甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基、三級丁氧基、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正己氧基等。
在本發明中,「C
1-C
6鹵烷氧基」係指(C
1-C
6鹵烷基)-O-基團,其中該鹵烷基部分具有上述含意,除非另有指明。例如,可述及二氟甲氧基、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-三級丁氧基、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, 3,3,4,4,5,55-七氟戊氧基、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氟己氧基、3,3,4,4,5,5,6,6,6-九氟己氧基、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。
在本發明中,「C
1-C
6烷氧基C
1-C
6烷基」意指其中C
1-C
6烷基的任何位置被C
1-C
6烷氧基取代的基團,其中該烷氧基部分及烷基部分具有上述含意,除非另有指明。例如,可述及甲氧基甲基、乙氧基甲基、正丙氧基甲基、異丙氧基甲基、三級丁氧基甲基、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4-乙氧基丁基等。
在本發明中,「C
1-C
6烷氧基C
1-C
6鹵烷基」意指其中C
1-C
6鹵烷基的任何位置被C
1-C
6烷氧基取代的基團,其中該烷氧基部分及鹵烷基部分具有上述含意,除非另有指明。例如,可述及由上述「C
1-C
6烷氧基」及「C
1-C
6鹵烷基」例示的那些基團的任意組合。
在本發明中,「C
1-C
6鹵烷氧基C
1-C
6烷基」意指其中C
1-C
6烷基的任何位置被C
1-C
6鹵烷氧基取代的基團,其中該鹵烷氧基部分及該烷基部分具有上述含意,除非另有指明。例如,可述及由上述「C
1-C
6鹵烷氧基」及「C
1-C
6烷基」例示的那些基團的任意組合。
在本發明中,「C
1-C
6鹵烷氧基C
1-C
6鹵烷基」意指其中C
1-C
6鹵烷基的任何位置被C
1-C
6鹵烷氧基取代的基團,其中該鹵烷氧基部分及該鹵烷基部分具有上述含意,除非另有指明。例如,可述及由上述「C
1-C
6鹵烷氧基」及「C
1-C
6鹵烷基」例示的那些基團的任意組合。
在本發明中,「C
3-C
6環烷基C
1-C
6烷基」意指其中C
1-C
6烷基的任何位置被C
3-C
6環烷基取代的基團,其中該環烷氧基部分及該烷基部分具有上述含意,除非另有指明。例如,可提及由上述「C
3-C
6環烷基」及「C
1-C
6烷基」例示的那些基團的任意組合。
在本發明中,「C
3-C
6鹵環烷基C
1-C
6烷基」意指其中C
1-C
6烷基的任何位置被C
3-C
6鹵環烷基取代的基團,其中該鹵環烷基部分及該烷基部分具有上述含意,除非另有指明。例如,可提及由上述「C
3-C
6鹵環烷基」及「C
1-C
6烷基」例示的那些基團的任意組合。
在本發明中,「C
3-C
6環烷基C
2-C
6烯基」意指其中C
2-C
6烯基的任何位置被C
3-C
6環烷基取代的基團,其中該環烷基部分及該烯基部分具有上述含意,除非另有指明。例如,可提及由上述「C
3-C
6環烷基」及「C
2-C
6烯基」例示的那些基團的任意組合。
在本發明中,「C
1-C
6鹵烷氧基C
1-C
6烷氧基」意指其中C
1-C
6烷氧基的任何位置被C
1-C
6鹵烷氧基取代的基團,其中該鹵烷氧基部分及該烷氧基部分具有上述含意,除非另有指明。例如,可提及由上述「C
1-C
6鹵烷氧基」及「C
1-C
6鹵烷基」例示的那些基團的任意組合。
在本發明中,「C
1-C
6烷氧基C
1-C
6鹵烷氧基」意指其中C
1-C
6鹵烷氧基的任何位置被C
1-C
6烷氧基取代的基團,其中該烷氧基部分及該鹵烷氧基部分,除非另有指明。例如,可提及由上述「C
1-C
6烷氧基」及「C
1-C
6鹵烷氧基」例示的那些基團的任意組合。
在本發明中,C
1-C
6鹵烷氧基C
1-C
6鹵烷氧基」意指其中C
1-C
6鹵烷氧基的任何位置被C
1-C
6鹵烷氧基取代的基團,其中該鹵烷氧基部分具有上述含意,除非另有指明。例如,可提及由上述「C
1-C
6鹵烷氧基」例示的那些基團的任意組合。該C
1-C
6鹵烷氧基可彼此相同或不同。
在本發明中,「C
3-C
6環烷氧基」係指(C
3-C
6環烷基)-O-基團,其中該環烷基部分具有上述含意,除非另有指明。例如,可提及環丙氧基、環丁氧基、環戊氧基或環己氧基等。
在本發明中,「C
3-C
6鹵環烷氧基」意指(C
3-C
6鹵環烷基)-O-基團,其中該鹵環烷基部分具有上述含意,除非另有指明。例如,可提及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4,4-二氯環己氧基等。
在本發明中,「C
3-C
6環烷基C
1-C
6烷氧基」意指其中C
1-C
6烷氧基的任何位置被C
3-C
6環烷基取代的基團,其中該環烷氧基部分及該烷氧基部分具有上述含意,除非另有指明。例如,可提及環丙基甲氧基、環丁基甲氧基、環戊基甲氧基或環己基甲氧基。
在本發明中,「C
3-C
6鹵環烷基C
1-C
6烷氧基」意指其中C
1-C
6烷氧基的任何位置被C
3-C
6鹵環烷基取代的基團,其中該鹵環烷基部分及該烷氧基部分具有上述含意,除非另有指明。例如,可提及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、及3,3-二氟環丁基甲氧基。
在本發明中,「C
6-C
12芳基」係指具有6至12個碳原子的芳基,除非另有指明。例如,可提及苯基、1-萘基及2-萘基。1-萘基亦稱為萘-1-基。2-萘基亦稱為萘-2-基。
在本發明中,「C
6-C
12芳氧基」係指(C
6-C
12芳基)-O-基團,除非另有指明。例如,可提及苯氧基、萘-1-基氧基、萘-2-基氧基等。
在本發明中,「C
7-C
14芳烷基」係指經具有7至14個碳原子的芳基取代之烷基,除非另有指明。例如,可提及C
6-C
12芳基C
1-C
2烷基、苯基C
1-C
2烷基等。C
7-C
14芳烷基的特定實例包括苄基、1-苯基乙基、2-苯基乙基、3-苯基丙基、4-苯基丁基、萘-1-基甲基、萘-2-基甲基等。此外,芳烷基亦稱為芳基烷基。
在本發明中,「C
7-C
14芳烷氧基」係指(C
7-C
14芳烷基)-O-基團,其中該芳烷基部分具有上述含意,除非另有指明。例如,可提及芐氧基、1-苯基乙氧基、2-苯基乙氧基、3-苯基丙氧基、4-苯基丁氧基、(萘-1-基)甲氧基、(萘-2-基)甲氧基等。
在本發明中,「C
5-C
12雜芳基」意指具有5至12個環成員原子的單環或稠合雙環結構,其具有一個或多個選自O、S及N之雜原子。雜原子的包含使得在5員環及6員環中具有芳族性。典型雜原子系統的實例包括單環C
5-C
6芳族基團,諸如吡啶基、嘧啶基、吡𠯤基、嗒𠯤基、三𠯤基、噻吩基、呋喃基、吡咯基、吡唑基、噻唑基、異噻唑基、㗁唑基、異㗁唑基、咪唑基、三唑基、噻二唑基、㗁二唑基或四唑基;可提及藉由這些單環基團中的一個與苯環或與任何雜芳單環基團稠合以形成C
8-C
10雙環基團的稠合雙環部分,諸如吲哚基、苯并咪唑基、 吲唑基、苯并三唑基、異喹啉基、喹啉基、苯并噻唑基、苯并呋喃基、苯并噻吩基、苯并異㗁唑基、吡唑并吡啶基、喹唑啉基、喹㗁啉基或㖕啉基等。
於此,取代位置並未被特別限制。即,雜芳基包括其所有位置的異構物。例如,當雜芳基為吡啶基時,吡啶基可為2-吡啶基、3-吡啶基或4-吡啶基。
在本發明中,「C
5-C
12雜芳氧基」意指(C
5-C
12雜芳基)-O-基團,其中該雜芳基部分具有上述含意,除非另有指明。
在本發明中,「C
6-C
14雜芳烷基」意指其中C
1-C
2烷基的任何位置被具有5至12個碳原子之雜芳基取代的烷基,其中該雜芳基部分具有上述含意,且該C
1-C
2烷基部分係指甲基或乙基,除非另有指明。例如,可提及吡啶基甲基、吡啶基乙基、吲哚基甲基、呋喃基甲基、噻吩基甲基、吡咯基甲基等。
在本發明中,「C
6-C
14雜芳烷氧基」意指(C
6-C
14雜芳烷基)-O-基團,其中該雜芳烷基部分具有上述含意,除非另有指明。例如,可提及吡啶基甲氧基、吡啶基乙氧基、吲哚基甲氧基、呋喃基甲氧基、噻吩基甲氧基、吡咯基甲基、吡咯基甲氧基等。
在本發明中,「五鹵氫硫基」係指經5個相同或不同鹵原子取代之λ
6-氫硫基,除非另有指明。例如,可提及氯四氟氫硫基或五氟氫硫基等。
在本發明中,「C
1-C
6烷基硫基」係指(C
1-C
6烷基)-S-基團,其中該烷基部分具有上述含意,除非另有指明。例如,可提及甲基硫基、乙基硫基、正丙基硫基、異丙基硫基、正丁基硫基、異丁基硫基、二級丁基硫基、三級丁基硫基、戊基硫基或己基硫基等。
在本發明中,「C
1-C
6烷基亞磺醯基」係指(C
1-C
6烷基)-S(=O)-基團,其中該烷基部分具有上述含意,除非另有指明。例如,可提及甲基亞磺醯基、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、二級丁基亞磺醯基、三級丁基亞磺醯基、戊基亞磺醯基或己基亞磺醯基等。
在本發明中,「C
1-C
6烷基磺醯基」係指(C
1-C
6烷基)-S(=O)
2-基團,其中該烷基部分具有上述含意,除非另有指明。例如,可提及甲基磺醯基、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、二級丁基磺醯基、三級丁基磺醯基、戊基磺醯基或己基磺醯基等。
在本發明中,「C
1-C
6鹵烷基硫基」係指(C
1-C
6鹵烷基)-S-基團,其中該鹵烷基部分具有上述含意,除非另有指明。例如,可提及氟甲基硫基、二氟甲基硫基、三氟甲基硫基、三氯甲基硫基、2,2,2-三氟乙基硫基、五氟乙基硫基、2,2,2-三氯乙基硫基、3,3,3-三氟丙基硫基、1,1,2,3,3,3-六氟丙基硫基、七氟丙基硫基、(1,1,1,3,3,3-六氟丙-2-基)硫基、(七氟丙-2-基)硫基或4,4,4-三氟丁基硫基等。
在本發明中,「C
1-C
6鹵烷基亞磺醯基」係指(C
1-C
6鹵烷基)-S(=O)-基團,其中該鹵烷基部分具有上述含意,除非另有指明。例如,可提及二氟甲基亞磺醯基、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七氟-2-丙基亞磺醯基等。
在本發明中,「C
1-C
6鹵烷基磺醯基」係指(C
1-C
6鹵烷基)-S(=O)
2-基團,其中該鹵烷基部分具有上述含意,除非另有指明。例如,可提及二氟甲基磺醯基、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、七氟-2-丙基磺醯基或九氟丁基磺醯基等。
在本發明中,「C
3-C
6環烷基硫基」係指(C
3-C
6環烷基)-S-基團,其中該環烷基部分具有上述含意,除非另有指明。例如,可提及環丙基硫基、環丁基硫基、環戊基硫基或環己基硫基等。
在本發明中,「C
3-C
6環烷基亞磺醯基」係指(C
3-C
6環烷基)-S(=O)-基團,其中該環烷基部分具有上述含意,除非另有指明。例如,可提及環丙基亞磺醯基、環丁基亞磺醯基、環戊基亞磺醯基或環己基亞磺醯基等。
在本發明中,「C
3-C
6環烷基磺醯基」係指(C
3-C
6環烷基)-S(=O)
2-基團,其中該環烷基部分具有上述含意,除非另有指明。例如,可提及環丙基磺醯基、環丁基磺醯基、環戊基磺醯基或環己基磺醯基等。
在本發明中,「C
3-C
6鹵環烷基硫基」係指(C
3-C
6鹵環烷基)-S-基團,其中該鹵環烷基部分具有上述含意,除非另有指明。例如,可提及2,2-二氟環丙基硫基、2,2-二氯環丙基硫基、3,3-二氟環丁基硫基、3,3-二氯環丁基硫基、3-氟環戊基硫基、3,3-二氟環戊基硫基、九氟環戊基硫基、3,3-二氯環戊基硫基、4,4-二氟環己基硫基或4,4-二氯環己基硫基等。
在本發明中,「C
3-C
6鹵環烷基亞磺醯基」係指(C
3-C
6鹵環烷基)-S(=O)-基團,其中該鹵環烷基部分具有上述含意,除非另有指明。例如,可提及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4,4-二氯環己基亞磺醯基等。
在本發明中,「C
3-C
6鹵環烷基磺醯基」係指(C
3-C
6鹵環烷基)-S(=O)
2-基團,其中該鹵環烷基部分具有上述含意,除非另有指明。例如,可提及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4,4-二氯環己基磺醯基等。
在本發明中,「C
1-C
6烷基磺醯氧基」係指(C
1-C
6烷基磺醯基)-O-基團,其中該烷基磺醯基部分具有上述含意,除非另有指明。例如,可提及甲基磺醯氧基、乙基磺醯氧基、正丙基磺醯氧基、異丙基磺醯氧基、正丁基磺醯氧基、異丁基磺醯氧基、二級丁基磺醯氧基、三級丁基磺醯氧基、戊基磺醯氧基或己基磺醯氧基等。
在本發明中,「C
1-C
6鹵烷基磺醯氧基」係指(C
1-C
6鹵烷基磺醯基)-O-基團,其中該鹵烷基磺醯基部分具有上述含意,除非另有指明。例如,二氟甲基磺醯氧基、三氟甲基磺醯氧基、三氯甲基磺醯氧基、2,2,2-三氟乙基磺醯氧基、五氟乙基磺醯氧基、3,3,3-三氟丙基磺醯氧基、七氟丙基磺醯氧基、七氟-2-丙基磺醯氧基或九氟丁基磺醯氧基等可提及。
在本發明中,「C
6-C
12芳基硫基」係指(C
6-C
12芳基)-S-基團,其中該芳基部分具有上述含意,除非另有指明。例如,可提及苯基硫基、1-萘基硫基、2-萘基硫基等。
在本發明中,「C
6-C
12芳基亞磺醯基」係指(C
6-C
12芳基)-S(=O)-基團,其中該芳基部分具有上述含意,除非另有指明。例如,可提及苯基亞磺醯基、1-萘基亞磺醯基、2-萘基亞磺醯基等。
在本發明中,「C
6-C
12芳基磺醯基」係指(C
6-C
12芳基)-S(=O)
2-基團,其中該芳基部分具有上述含意,除非另有指明。例如,可提及苯基磺醯基、1-萘基磺醯基、2-萘基磺醯基等。
在本發明中,「C
5-C
12雜芳基硫基」係指(C
5-C
12雜芳基)-S-基團,其中該芳基部分具有上述含意,除非另有指明。例如,可提及吡啶-2-基硫基、吡啶-3-基硫基、吡啶-4-基硫基、吡𠯤-2-基硫基、嗒𠯤-3-基硫基、嗒𠯤-4-基硫基、嘧啶-2-基硫基、嘧啶-4-基硫基、嘧啶-5-基硫基、噻唑-2-基硫基、噻唑-4-基硫基或噻唑-5-基硫基等。
在本發明中,「C
5-C
12雜芳基亞磺醯基」係指(C
5-C
12雜芳基)-S(=O)-基團,其中該芳基部分具有上述含意,除非另有指明。例如,可提及吡啶-2-基亞磺醯基、吡啶-3-基亞磺醯基、吡啶-4-基亞磺醯基、吡𠯤-2-基亞磺醯基、嗒𠯤-3-基亞磺醯基、嗒𠯤-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。
在本發明中,「C
5-C
12雜芳基磺醯基」係指(C
5-C
12雜芳基)-S(=O)
2-基團,其中該芳基部分具有上述含意,除非另有指明。例如,可提及吡啶-2-基磺醯基、吡啶-3-基磺醯基、吡啶-4-基磺醯基、吡𠯤-2-基磺醯基、嗒𠯤-3-基磺醯基、嗒𠯤-4-基磺醯基、嘧啶-2-基磺醯基、嘧啶-4-基磺醯基、嘧啶-5-基磺醯基、噻唑-2-基磺醯基、噻唑-4-基磺醯基或噻唑-5-基磺醯基等。
在本發明中,「C
6-C
12芳基磺醯氧基」係指(C
6-C
12芳基磺醯基)-O-基團,其中該芳基磺醯基部分具有上述含意,除非另有指明。例如,可提及苯基磺醯氧基、1-萘基磺醯氧基、2-萘基磺醯氧基等。
在本發明中,「C
1-C
6鹵烷基硫基C
1-C
6烷氧基」意指其中該C
1-C
6烷氧基的任何位置被C
1-C
6鹵烷基硫基取代的基團,其中該鹵烷基硫基部分及該烷氧基部分具有上述含意,除非另有指明。
在本發明中,「C
1-C
6鹵烷基亞磺醯基C
1-C
6烷氧基」意指其中該C
1-C
6烷氧基的任何位置被C
1-C
6鹵烷基亞磺醯基取代的基團,其中該鹵烷基亞磺醯基部分及烷氧基部分具有上述含意,除非另有指明。
在本發明中,「C
1-C
6鹵烷基磺醯基C
1-C
6烷氧基」意指其中該C
1-C
6烷氧基的任何位置被C
1-C
6鹵烷基磺醯基取代的基團,其中該鹵烷基磺醯基部分及烷氧基部分具有上述含意,除非另有指明。
在本發明中,「C
3-C
6環烷基C
1-C
6烷基硫基」意指其中該C
1-C
6烷基硫基的任何位置被C
3-C
6環烷基取代的基團,其中該環烷基部分及該烷基硫基部分具有上述含意,除非另有指明。
在本發明中,「C
3-C
6環烷基C
1-C
6烷基亞磺醯基」意指其中該C
1-C
6烷基亞磺醯基的任何位置被C
3-C
6環烷基取代的基團,其中該環烷基部分及該烷基亞磺醯基部分具有上述含意,除非另有指明。
在本發明中,「C
3-C
6環烷基C
1-C
6烷基磺醯基」意指其中該C
1-C
6烷基磺醯基的任何位置被C
3-C
6環烷基取代的基團,其中該環烷基部分及該烷基磺醯基部分具有上述含意,除非另有指明。
在本發明中,「C
3-C
6鹵環烷基C
1-C
6烷基硫基」意指其中該C
1-C
6烷基硫基的任何位置被C
3-C
6鹵環烷基取代的基團,其中該鹵環烷基部分及該烷基硫基部分具有上述含意,除非另有指明。
在本發明中,「C
3-C
6鹵環烷基C
1-C
6烷基亞磺醯基」意指其中該C
1-C
6烷基亞磺醯基的任何位置被C
3-C
6鹵環烷基取代的基團,其中該鹵環烷基部分及該烷基亞磺醯基部分具有上述含意,除非另有指明。
在本發明中,「C
3-C
6鹵環烷基C
1-C
6烷基磺醯基」意指其中該C
1-C
6烷基磺醯基的任何位置被C
3-C
6鹵環烷基取代的基團,其中該鹵環烷基部分及該烷基磺醯基部分具有上述含意,除非另有指明。
在本發明中,「羥基C
1-C
6烷氧基」意指其中該烷氧基的任何位置被「HO-」取代的基團。
在本發明中,「羥基C
3-C
6環烷氧基」意指其中該環烷氧基的任何位置被「HO-」取代的基團。
在本發明中,「羥基亞胺基C
1-C
6烷基」意指其中該烷基的任何位置被「HO- N=」取代的基團。
在本發明中,「C
1-C
6烷氧基亞胺基C
1-C
6烷基」意指其中該烷基的任何位置被「(C
1-C
6烷氧基)-N=」取代的基團。
在本發明中,「C
1-C
6鹵烷氧基亞胺基C
1-C
6烷基」意指其中該烷基的任何位置被「(C
1-C
6鹵烷氧基)-N=」取代的基團。
在本發明中,「氰基C
1-C
6烷基」意指其中該C
1-C
6烷基的任何位置被氰基取代的基團,其中該烷基部分具有上述含意,除非另有指明。例如,可提及氰基甲基、1-氰基乙基、2-氰基乙基、3-氰基丙基、2-氰基丙-2-基、1-氰基丁基、4-氰基丁基、5-氰基戊基或6-氰基己基等。
在本發明中,「氰基C
3-C
6環烷基」意指其中該C
3-C
6環烷基的任何位置被氰基取代的基團,其中該環烷基部分具有上述含意,除非另有指明。例如,可提及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-氰基環己基或4-氰基環己基等。
在本發明中,「羥基C
1-C
6烷基」意指其中該C
1-C
6烷基的任何位置被羥基取代的基團,其中該烷基部分具有上述含意,除非另有指明。例如,可提及羥基甲基、1-羥基乙基、2-羥基乙基、3-羥基丙基、2-羥基丙烷-2-基、1-羥基丁基、4-羥基丁基、5-羥基戊基或6-羥基己基等。
在本發明中,「羥基C
3-C
6環烷基」意指其中該環烷基的任何位置被羥基取代的基團,其中該環烷基部分具有上述含意,除非另有指明。例如,可提及1-羥基環丙基、2-羥基環丙基、1-羥基環丁基、2-羥基環丁基、3-羥基環丁基、1-羥基環戊基、3-羥基環戊基、1-羥基環己基或4-羥基環己基等。
在本發明中,「氰基C
3-C
6環烷氧基」意指其中該C
3-C
6環烷氧基的任何位置被氰基取代的基團,其中該環烷氧基部分具有上述含意,除非另有指明。例如,可提及1-氰基環丙氧基、2-氰基環丙氧基、1-氰基環丁氧基、2-氰基環丁氧基、3-氰基環丁氧基、1-氰基環戊氧基、3-氰基環戊氧基、1-氰基環己氧基或4-氰基環己氧基等。
在本發明中,「氰基C
1-C
6烷氧基」意指其中該C
1-C
6烷氧基的任何位置被氰基取代的基團,其中該烷氧基部分具有上述含意,除非另有指明。例如,可提及氰基甲氧基、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6-氰基己氧基等。
在本發明中,「(氰基C
3-C
6環烷基)C
1-C
6烷氧基」意指其中該C
1-C
6烷氧基的任何位置被氰基C
3-C
6環烷基取代的基團,其中該氰基C
3-C
6環烷基部分及該烷氧基部分具有上述含意,除非另有指明。例如,可提及(1-氰基環丙基)甲氧基、(2-氰基環丙基)甲氧基、(1-氰基環丁基)甲氧基、(2-氰基環丁基)甲氧基、(3-氰基環丁基)甲氧基、(1-氰基環戊基)甲氧基、(3-氰基環戊基)甲氧基、(1-氰基環己基)甲氧基或(4-氰基環己基)甲氧基等。
在本發明中,「單(C
1-C
6烷基) 胺基」係指(C
1-C
6烷基)-NH-基團,其中該烷基部分具有上述含意,除非另有指明。例如,可提及甲基胺基、乙基胺基、異丙基胺基、正丙基胺基或三級丁基胺基等。
在本發明中,「二(C
1-C
6烷基)胺基」係指(C
1-C
6烷基)
2-N-基團,其中該烷基部分具有上述含意,且該二個烷基可彼此不同,除非另有指明。例如,可提及二甲基胺基、甲基乙基胺基或甲基-正丙基胺基等。
在本發明中,「(二(C
1-C
6烷基)亞磺醯亞基)胺基」係指O = S (C
1-C
6烷基)
2= N-基團,其中該二個烷基可彼此不同。例如,可提及(S,S-二甲基亞磺醯亞基)胺基、(S,S-二乙基亞磺醯亞基)胺基、(S-乙基-S-甲基亞磺醯亞基)胺基等。
在本發明中,「二(C
1-C
6烷基)磷醯基」係指O = P (C
1-C
6烷基)
2基團,其中該二個烷基可彼此不同。例如,可提及二甲基磷醯基、二乙基磷醯基、乙基甲基磷醯基等。
在本發明中,「C
1-C
7醯基」係指H-C(=O)-基團或(C
1-C
6烷基)-C(=O)-基團,除非另有指明。例如,可提及甲醯基、乙醯基、丙醯基、異丁醯基或三甲基乙醯基等。
「未經取代或經鹵原子取代之C
1-C
7醯基」在其可取代的位置處可具有1至10個,較佳為1至5個鹵原子。當鹵原子之數目為二個或更多個時,該鹵原子可相同或不同。
在本發明中,「C
1-C
7醯氧基」係指(C
1-C
7醯基)-O-基團,其中該醯基部分具有上述含意,除非另有指明。例如,可提及甲醯氧基、乙醯氧基、丙醯氧基、異丁醯氧基或三甲基乙醯氧基等。
在本發明中,「C
1-C
7鹵醯基」係指經鹵素取代的甲醯基或(C
1-C
6鹵烷基)-C(=O)-基團,除非另有指明。例如,可提及氯甲醯基、氯乙醯基、三氟乙醯基、三氯乙醯基、2-氯丙醯基、2-氯異丁醯基、2-溴異丁醯基或3-氯三甲基乙醯基等。
在本發明中,「羥基亞胺基(胺基)C
1-C
6烷基」意指(H
2N)C(=NOH)-基團或其中該C
1-C
6烷基的任何位置被「(H
2N)C(=NOH)-」取代的基團。
在本發明中,「羧基」係指HO-C(=O)-基團。
在本發明中,「C
1-C
6烷氧基羰基」係指(C
1-C
6烷氧基)-C(=O)-基團。
在本發明中,「N-(C
1-C
6烷氧基)-N-(C
1-C
6烷基)胺基羰基」係指(C
1-C
6烷氧基)(C
1-C
6烷基)N-C(=O)-基團。
在本發明中,「胺基羰基」係指NH
2-C(=O)-基團。
在本發明中,「胺基硫羰基」係指NH
2-C(=S)-基團。
在本發明中,「單(C
1-C
6烷基) 胺基羰基」係指(C
1-C
6烷基)-NH-C(=O)-基團,其中該烷基部分具有上述含意,除非另有指明。例如,可提及甲基胺基羰基、乙基胺基羰基、丙基胺基羰基、異丙基胺基羰基或三級丁基胺基羰基等。
在本發明中,「單(氰基C
3-C
6環烷基) 胺基羰基」係指(氰基C
3-C
6環烷基)-NH-C(=O)-基團,其中該氰基C
3-C
6環烷基部分具有上述含意,除非另有指明。例如,可提及1-氰基環丙基胺基羰基、2-氰基環丙基胺基羰基、1-氰基環丁基胺基羰基、2-氰基環丁基胺基羰基、3-氰基環丁基胺基羰基、1-氰基環戊基胺基羰基、3-氰基環戊基胺基羰基、1-氰基環己基胺基羰基或4-氰基環己基胺基羰基等。
在本發明中,「單(C
1-C
6烷氧基亞胺基C
1-C
6烷基)胺基羰基」係指(C
1-C
6烷氧基亞胺基C
1-C
6烷基)-NH-C(= O)-基團,其中該C
1-C
6烷氧基亞胺基C
1-C
6烷基部分具有上述含意,除非另有指明。例如,可提及甲氧基亞胺基甲基胺基羰基、乙氧基亞胺基甲基胺基羰基等。
在本發明中,「二(C
1-C
6烷基)胺基亞甲基胺基羰基」係指(C
1-C
6烷基)
2-N-C=N-C(= O)-基團,其中該烷基部分具有上述含意,除非另有指明。例如,可提及二甲基胺基亞甲基胺基羰基、二乙基胺基亞甲基胺基羰基或二異丙基胺基亞甲基胺基羰基等。
在本發明中,「單(C
1-C
6烷基) 胺基硫羰基」係指(C
1-C
6烷基)-NH-C(=S)-基團,其中該烷基部分具有上述含意,除非另有指明。
在本發明中,「二(C
1-C
6烷基)胺基羰基」係指(C
1-C
6烷基)
2-N-C(=O)-基團,其中該烷基部分具有上述含意,且該二個烷基可彼此不同,除非另有指明。例如,可提及二甲基胺基羰基、二乙基胺基羰基或二異丙基胺基羰基等。
在本發明中,「二(C
1-C
6烷基)胺基硫羰基」係指(C
1-C
6烷基)
2-N-C(=S)-基團,其中該烷基部分具有上述含意,且該二個烷基可彼此不同,除非另有指明。
在本發明中,「單(C
1-C
6鹵烷基)胺基羰基」係指(C
1-C
6鹵烷基)-NH-C(=O)-基團,其中該鹵烷基部分具有上述含意,除非另有指明。例如,可提及2-氟乙基胺基羰基、2,2-二氟乙基胺基羰基、2,2,2-三氟乙基胺基羰基、2,2,2-三氯乙基胺基羰基或1,1,1,3,3,3-六氟-2-丙基胺基羰基等。
在本發明中,「單(C
3-C
6環烷基)胺基羰基」係指(C
3-C
6環烷基)-NH-C(=O)-基團,其中該環烷基部分具有上述含意,除非另有指明。例如,可提及環丙基胺基羰基、環丁基胺基羰基、環戊基胺基羰基、環己基胺基羰基等。
在本發明中,諸如「未經取代或可選擇地經R
11取代之C
6-C
12芳基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的芳基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當芳基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,諸如「未經取代或可選擇地經R
11取代的C
5-C
12雜芳基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的雜芳基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當雜芳基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,諸如「未經取代或可選擇地經R
11取代的C
7-C
14芳烷基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的芳烷基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當芳烷基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,諸如「未經取代或可選擇地經R
11取代的C
6-C
14雜芳烷基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的雜芳烷基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當雜芳烷基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,諸如「未經取代或可選擇地經R
11取代的C
6-C
12芳氧基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的芳氧基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當芳氧基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,諸如「未經取代或可選擇地經R
11取代的C
5-C
12雜芳氧基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的雜芳氧基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當雜芳氧基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,諸如「未經取代或可選擇地經R
11取代的C
7-C
14芳烷氧基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的芳烷氧基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當芳烷氧基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,諸如「未經取代或可選擇地經R
11取代的C
6-C
14雜芳烷氧基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的雜芳烷氧基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當雜芳烷氧基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,標記「未經取代或可選擇地經R
11取代的雜環基」代表其中結合至碳原子之氫原子被任何R
11取代的雜環基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當雜環基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
在本發明中,雜環基意指具有一個或多個相同或不同的雜原子(例如氮原子、氧原子及/或硫原子)替代一個或多個碳原子的非芳族、單環或多環基團。
在本發明中,雜環基的實例包括,但不限於具有1至13個碳原子及1至4個獨立選自氮、氧和硫原子之雜原子的非芳族、單環、雙環或三環及3至14員(較佳為4至14員且更佳為5至14員)雜環基。
在本發明中,雜環基之實例包括,但不限於具有1至9個碳原子及1至4個獨立選自氮、氧和硫原子之雜原子的非芳族、單環、雙環及3至10員(較佳為4至10員,且更佳為5至10員,且甚至更佳為5至7員)雜環基。
進一步地,在本發明中,雜環基之實例包括,但不限於具有1至5個碳原子及1至4個獨立選自氮、氧和硫原子之雜原子的非芳族、單環及3至8員(較佳為5至6員)雜環基。
單環雜環基之特定實例包括,但不限於,異㗁唑啉基、哌啶基、哌𠯤基、四氫吖唉基、氮丙啶基、嗎啉基、二氫哌喃基、四氫哌喃基、四氫呋喃基、氧呾基、環氧乙烷基、二㗁烷基(例如,1,3-二㗁烷基、1,4-二㗁烷基等)、二環氧乙烷基 (例如,1,3-二氧雜環戊烷基等)、噻嗯基(thianyl)、四氫噻吩基、噻坦基(thietanyl)、噻丙環基(thiiranyl)等。
雙環雜環基之特定實例包括,但不限於吲哚啉基、異吲哚啉基、苯并二氫哌喃基、異苯并二氫哌喃基、四氫異喹啉基、苯并四氫呋喃基、苯并四氫噻吩基、四氫異苯并呋喃基、四氫異苯并噻吩基、苯并二氧戊基、二氫苯并異㗁𠯤基、二氫苯并異噻𠯤基、1-氧橋四氫喹啉基、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、二氫異香豆素基、異吲哚啉酮-基、苯并二㗁烷基、苯并㗁唑啉酮-基、喹啶基、吲啶基、莨菪烷基、降莨菪烷基(nortropanyl)、奎寧環基(quinuclidinyl)、3-氮雜雙環[3.1.0]己基、6-氧雜-3-氮雜雙環[3.1.0]己基等。
於此,取代的位置並沒有特別限制。即,雜環基包括所有其位置異構物。例如,當雜環基為哌啶基時,該哌啶基包含1-哌啶基、2-哌啶基、3-哌啶基及4-哌啶基。
如上述定義或例示之雜環基,如果可能,可包括非稠合環狀(例如,單環或螺環)及稠合環狀基團。
如上述定義或例示之雜環基,如果可能,可以是未飽和、部分飽和或飽和的。
當如上述定義或例示之雜環基的雜原子為氮原子時,該氮原子可為N-氧化物。
當如上述定義或例示之雜環基的雜原子為硫原子時,該硫原子可為亞磺醯基 (-SO-)或磺醯基 (-SO
2-)。
在本發明中,「雜環基C
1-C
6烷基」意指其中該C
1-C
6烷基之任何位置被雜環基取代的基團,其中該雜環基部分及該烷基部分具有上述含意,除非另有指明。例如,可提及(1,3-二㗁烷-2-基)甲基等。
在本發明中,諸如「未經取代或可選擇地經R
11取代的雜環基C
1-C
6烷基」之標記代表其中結合至碳原子之氫原子被任何R
11取代的雜環基C
1-C
6烷基。被取代的R
11的數目在每個指定的碳原子數目的範圍內可選擇地選定,例如,1至10個,較佳為1至5個。當雜環基C
1-C
6烷基上有二個或更多個取代基R
11時,各R
11可彼此相同或不同。
當羥基、羧基或胺基或吡啶環的氮原子存在於通式[I]表示之本發明化合物的結構中時,本發明中的鹽或農業上可接受的鹽是由這些基團或原子與金屬或有機鹼形成的鹽,或與無機酸或有機酸形成的鹽。該金屬的實例包括諸如鈉和鉀的鹼金屬或諸如鎂和鈣的鹼土金屬。該有機鹼的實例包括三乙胺或二異丙胺等。該無機酸的實例包括磷酸、氫氯酸、氫溴酸、氫碘酸、硼酸或硫酸等。此外,該有機酸的實例包括甲酸、乙酸、乳酸、抗壞血酸、琥珀酸、富馬酸、馬來酸、草酸、檸檬酸、苯甲酸、水楊酸、酒石酸、甲磺酸、4-甲苯磺酸或三氟甲磺酸等。
隨後,將本發明通式[I]表示的雜環化合物中所含的化合物的代表實例顯示於表1至表23。然而,包括於本發明雜環化合物中的化合物並不限於此。此外,表中的化合物編號將在以下描述中提及。
雖然包括於本發明雜環化合物中的化合物根據取代基的種類可以含有E型和Z型的幾何異構體,但E型、Z型、以及E型和Z型的任意比例的混合物均包含在本發明中。此外,雖然包括在本發明中的化合物由於存在一個或多個不對稱碳原子和不對稱硫原子而可含有光學異構物,但所有光學活性物質、外消旋化合物或非鏡像異構物都包括在本發明中。
本文表格中的下列符號分別代表例如對應的基團,如下所示:
Me:甲基,
Et:乙基,
nPr:正丙基,
iPr:異丙基,
cPr:環丙基,
nBu:正丁基,
sBu:二級丁基,
iBu:異丁基,
tBu:三級丁基,
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-F
2)cPr:2,2-二氟環丙基,
Ph:苯基,
(4-CF
3)Ph:4-三氟甲基苯基,
製造方法另一方面,通式[I]代表的本發明化合物可根據以下所示之製造方法製造,但其製造方法並不受此限。在下文中,例如「由通式[I]代表的化合物」、「由式[I]代表的化合物」和「化合物[I]」為相同的表示方式。
製造方法1
在本發明化合物之中,通式[I]代表的化合物可例如根據由以下例示之反應式組成的方法來製造。
(其中,X代表鹵原子、或C
1-C
6烷基磺醯基、C
1-C
6鹵烷基磺醯基、可選擇地經取代C
6-C
12芳基磺醯基、C
1-C
6烷基磺醯氧基、C
1-C
6鹵烷基磺醯氧基、可選擇地經取代C
6-C
12芳基磺醯氧基或C
1-C
7醯氧基,W
1、W
2、m、n、R
1、R
2、A
1、A
2、A
3、A
4、A
5、A
6、A
7、A
8、A
9及R
10具有如上述相同的含義。)
即,通式[I]代表的化合物可藉由在合適的溶劑中,於存在或不存在合適之鹼的情況下,使通式[II]代表的化合物與通式[III]代表的化合物反應來製備。此外,此反應亦可在合適的催化劑存在下進行。
相對於1 mol化合物[II],此反應中所使用之化合物[III]的量通常可在1至100 mol的範圍內適當選擇,較佳為1至5 mol。
當在此反應中使用鹼時,該可使用的鹼的實例包括鹼金屬氫氧化物,諸如氫氧化鋰、氫氧化鈉及氫氧化鉀;鹼土金屬氫氧化物、諸如氫氧化鈣及氫氧化鎂;鹼金屬碳酸鹽,諸如碳酸鋰、碳酸鈉、碳酸鉀及碳酸銫;鹼金屬碳酸氫鹽,諸如碳酸氫鈉及碳酸氫鉀;鹼金屬氟化物,諸如氟化鈉及氟化鉀;無機鹼,諸如磷酸三鉀;金屬氫化物,諸如氫化鋰、氫化鈉、氫化鉀;或有機鹼,諸如三乙基胺、三丁基胺、N,N-二異丙基乙基胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯。相對於1 mol的化合物[II],所使用之鹼的量可在0至5 mol的範圍內適當選擇,較佳為0.1至2 mol。
可使用於此反應的溶劑的實例包括醚類,諸如二乙醚、甲基三級丁基醚、環戊基甲基醚、四氫呋喃、2-甲基四氫呋喃、1,4-二㗁烷、單甘醇二甲醚;芳香烴,諸如苯、甲苯、二甲苯、對稱三甲苯、氯苯;鹵代烴,諸如二氯甲烷、氯仿、1,2-二氯乙烷;非質子極性溶劑,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮;醇類,諸如甲醇、乙醇、2-丙醇、三級丁醇、2-甲氧乙醇;腈類,諸如乙腈及丙腈;脂肪烴,諸如戊烷、己烷、環己烷及庚烷;吡啶,諸如吡啶、甲吡啶及二甲吡啶;三級胺,諸如三乙胺及三丁胺;水或其之混合溶劑等。相對於1 mol的化合物[II],所使用之溶劑的量為0.1至1000公升,較佳為0.2至100公升。
當在此反應中使用催化劑時,該可使用的催化劑包括金屬或金屬鹽及作為配體的化合物。此類催化劑可在反應系統中(原位)由金屬或金屬鹽和作為後述的配體的化合物製備,或者可在反應系統外預先製備,然後再添加至反應系統中。催化劑可包含除金屬或金屬鹽及化合物配體之外的其他成分。金屬或金屬鹽之實例包括銅化合物,諸如金屬銅、乙酸銅(單價)、乙酸銅(雙價)、氧化銅(單價)、氧化銅(雙價)、氯化銅(單價)及碘化銅(單價);鈀化合物,諸如鈀碳、氯化鈀、硝酸鈀、乙酸鈀、雙(三苯基膦鈀二氯化物、四(三苯基膦)鈀、三(二亞芐基丙酮)二鈀等。配體之實例包括伸乙基二胺、N,N-二甲基伸乙基二胺、N,N'-二甲基伸乙基二胺、四甲基伸乙基二胺、2,2'-聯吡啶、1,10-啡啉、新亞銅試劑(neocuproine)、3,4,7,8-四甲基-1,10-啡啉、2,9-聯苯基-1,10-啡啉、4,7-聯苯基-1,10-啡啉、4,5-雙(聯苯基膦)-9,9-二甲基二苯并哌喃、三苯基膦、1,1'-雙(聯苯基膦)二茂鐵等,及其鹽。相對於1 mol的金屬或金屬鹽,金屬或金屬鹽與作為配體的化合物的組合可從0.1至10 mol的範圍內適當選擇,且較佳為1至4 mol的作為配體的化合物。相對於1 mol的化合物[II],所使用之催化劑的量以金屬或金屬鹽計可在0.001至10 mol的範圍內適當選擇,且較佳為0.01至5 mol。
此反應的反應溫度可選自-78℃至反應體系中之回流溫度的範圍內的任意溫度。反應較佳在0℃至180℃的溫度範圍內進行。
雖然此反應的反應時間依據反應溫度、反應基質、反應量等而變化,但通常為10分鐘至48小時。
反應完成後,可藉由諸如將反應混合物加入水中並濾出沉澱的固體,或以有機溶劑萃取反應混合物然後濃縮的程序分離化合物[I]。若需要,分離的化合物[I]可藉由管柱層析、再結晶、蒸餾等進一步純化。
製造方法2
在本發明化合物之中,通式[I]代表的化合物可例如根據下例方法製造。
其中,X、W
1、W
2、m、n、R
1、R
2、A
1、A
2、A
3、A
4、A
5、A
6、A
7、A
8、A
9及R
10具有如上述相同的含義。)
即,通式[I]代表的化合物可藉由在合適的溶劑中,於存在或不存在合適之鹼的情況下,使通式[IV]代表的化合物與通式[V]代表的化合物反應來製備。此外,此反應亦可在合適的催化劑存在下進行。
相對於1 mol化合物[IV],此反應中所使用之化合物[V]的量通常可在1至100 mol的範圍內適當選擇,較佳為1至5 mol。
當在此反應中使用鹼時,該可使用的鹼的實例包括鹼金屬氫氧化物,諸如氫氧化鋰、氫氧化鈉及氫氧化鉀;鹼土金屬氫氧化物、諸如氫氧化鈣及氫氧化鎂;鹼金屬碳酸鹽,諸如碳酸鋰、碳酸鈉、碳酸鉀及碳酸銫;鹼金屬碳酸氫鹽,諸如碳酸氫鈉及碳酸氫鉀;鹼金屬氟化物,諸如氟化鈉及氟化鉀;無機鹼,諸如磷酸三鉀;金屬氫化物,諸如氫化鋰、氫化鈉、氫化鉀;或有機鹼,諸如三乙基胺、三丁基胺、N,N-二異丙基乙基胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯。相對於1 mol 化合物[IV],所使用之鹼的量可在0至5 mol的範圍內適當選擇,較佳為0.1至2 mol。
可使用於此反應的溶劑的實例包括醚類,諸如二乙醚、甲基三級丁基醚、環戊基甲基醚、四氫呋喃、2-甲基四氫呋喃、1,4-二㗁烷、單甘醇二甲醚;芳香烴,諸如苯、甲苯、二甲苯、對稱三甲苯、氯苯;鹵代烴,諸如二氯甲烷、氯仿、1,2-二氯乙烷;非質子極性溶劑,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮;醇類,諸如甲醇、乙醇、2-丙醇、三級丁醇、2-甲氧乙醇;腈類,諸如乙腈及丙腈;脂肪烴,諸如戊烷、己烷、環己烷及庚烷;吡啶,諸如吡啶、甲吡啶及二甲吡啶;三級胺,諸如三乙胺及三丁胺;水或其之混合溶劑等。相對於1 mol的化合物[IV],所使用之溶劑的量為0.1至1000公升,較佳為0.2至100公升。
當在此反應中使用催化劑時,該可使用的催化劑包括金屬或金屬鹽及作為配體的化合物。此類催化劑可在反應系統中(原位)由金屬或金屬鹽和作為後述的配體的化合物製備,或者可在反應系統外預先製備,然後再添加至反應系統中。催化劑可包含除金屬或金屬鹽及化合物配體之外的其他成分。金屬或金屬鹽之實例包括銅化合物,諸如金屬銅、乙酸銅(單價)、乙酸銅(雙價)、氧化銅(單價)、氧化銅(雙價)、氯化銅(單價)及碘化銅(單價);鈀化合物,諸如鈀碳、氯化鈀、硝酸鈀、乙酸鈀、雙(三苯基膦鈀二氯化物、四(三苯基膦)鈀、三(二亞芐基丙酮)二鈀等。配體之實例包括伸乙基二胺、N,N-二甲基伸乙基二胺、N,N'-二甲基伸乙基二胺、四甲基伸乙基二胺、2,2'-聯吡啶、1,10-啡啉、新亞銅試劑(neocuproine)、3,4,7,8-四甲基-1,10-啡啉、2,9-聯苯基-1,10-啡啉、4,7-聯苯基-1,10-啡啉、4,5-雙(聯苯基膦)-9,9-二甲基二苯并哌喃、三苯基膦、1,1'-雙(聯苯基膦)二茂鐵等,及其鹽。相對於1 mol的金屬或金屬鹽,金屬或金屬鹽與作為配體的化合物的組合可從0.1至10 mol的範圍內適當選擇,且較佳為1至4 mol的作為配體的化合物。相對於1 mol的化合物[IV],所使用之催化劑的量以金屬或金屬鹽計可在0.001至10 mol的範圍內適當選擇,且較佳為0.01至5 mol。
此反應的反應溫度可選自-78℃至反應體系中之回流溫度的範圍內的任意溫度。反應較佳在0℃至180℃的溫度範圍內進行。
雖然此反應的反應時間依據反應溫度、反應基質、反應量等而變化,但通常為10分鐘至48小時。
反應完成後,可藉由諸如將反應混合物加入水中並濾出沉澱的固體,或以有機溶劑萃取反應混合物然後濃縮的程序分離化合物[I]。若需要,分離的化合物[I]可藉由管柱層析、再結晶、蒸餾等進一步純化。
製造方法3
在本發明化合物之中,通式[IX]代表的化合物亦可例如根據下例方法製造。
(其中,R
14代表氫原子、鹵原子、C
1-C
6鹵烷基及C
1-C
6鹵烷氧基,R
10’代表在R
10中非氫原子的其他取代基,且X、W
1、W
2、m、n、R
1、R
2、A
1、A
2、A
3、A
4、A
5、A
6、A
7、A
8及A
9具有如上述相同的含義。)
即,通式[IX]代表的化合物可藉由在合適的溶劑中,於存在或不存在合適之鹼的情況下,使通式[VI]代表的化合物與化合物[VII]或化合物[VIII]反應來製備。
相對於1 mol 化合物[VI],此反應中所使用之化合物[VII]或化合物[VIII]的量通常可在1至10 mol的範圍內適當選擇,較佳為1至2 mol。
當在此反應中使用鹼時,該可使用的鹼的實例包括鹼金屬氫氧化物,諸如氫氧化鋰、氫氧化鈉及氫氧化鉀;鹼土金屬氫氧化物,諸如氫氧化鈣及氫氧化鎂;鹼金屬碳酸鹽,諸如碳酸鋰、碳酸鈉、碳酸鉀及碳酸銫;鹼金屬碳酸氫鹽,諸如碳酸氫鈉及碳酸氫鉀;鹼金屬氟化物,諸如氟化鈉及氟化鉀;無機鹼,諸如磷酸三鉀;金屬氫化物,諸如氫化鋰、氫化鈉、氫化鉀;金屬醇鹽,諸如甲醇鈉、乙醇鈉、三級丁醇鉀;或有機鹼,諸如三乙胺、三丁胺、N,N-二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯。相對於1 mol 化合物[VI],所使用之鹼的量可在0至10 mol的範圍內適當選擇,較佳為0至5 mol。
可使用於此反應的溶劑的實例包括醚類,諸如二乙醚、甲基三級丁基醚、環戊基甲基醚、四氫呋喃、2-甲基四氫呋喃、1,4-二㗁烷、單甘醇二甲醚;芳香烴,諸如苯、甲苯、二甲苯、對稱三甲苯、氯苯;鹵代烴,諸如二氯甲烷、氯仿、1,2-二氯乙烷;非質子極性溶劑,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮;醇類,諸如甲醇、乙醇、2-丙醇、三級丁醇、2-甲氧乙醇;腈類,諸如乙腈及丙腈;脂肪烴,諸如戊烷、己烷、環己烷及庚烷;吡啶,諸如吡啶、甲吡啶及二甲吡啶;三級胺,諸如三乙胺及三丁胺;水或其之混合溶劑等。相對於1 mol的化合物[VI],所使用之溶劑的量為0.1至1000公升,較佳為0.2至100公升。
此反應的反應溫度可選自-78℃至反應體系中之回流溫度的範圍內的任意溫度。反應較佳在0℃至100°C的溫度範圍內進行。
雖然此反應的反應時間依據反應溫度、反應基質、反應量等而變化,但通常為10分鐘至24小時。
反應完成後,可藉由諸如將反應混合物加入水中並濾出沉澱的固體,或以有機溶劑萃取反應混合物然後濃縮的程序分離化合物[IX]。若需要,分離的化合物[IX]可藉由管柱層析、再結晶、蒸餾等進一步純化。
製造方法4
在本發明化合物之中,通式[I]代表的化合物亦可例如根據下例方法製造。
(其中,X、W
1、W
2、m、n、R
1、R
2、A
1、A
2、A
3、A
4、A
5、A
6、A
7、A
8、A
9及R
10具有如上述相同的含義。)
即,通式[I]代表的化合物可藉由在合適的溶劑中,於存在或不存在合適之鹼的情況下,使通式[X]代表的化合物與通式[XI]代表的化合物反應來製備。此外,此反應亦可在合適的催化劑存在下進行。
相對於1 mol 化合物[X],此反應中所使用之化合物[XI]的量通常可在1至5 mol的範圍內適當選擇,且較佳為1至1.5 mol。
當在此反應中使用鹼時,該可使用的鹼的實例包括鹼金屬氫氧化物,諸如氫氧化鋰、氫氧化鈉及氫氧化鉀;鹼土金屬氫氧化物,諸如氫氧化鈣及氫氧化鎂;鹼金屬碳酸鹽,諸如碳酸鋰、碳酸鈉、碳酸鉀及碳酸銫;鹼金屬碳酸氫鹽,諸如碳酸氫鈉及碳酸氫鉀;鹼金屬氟化物,諸如氟化鈉及氟化鉀;無機鹼,諸如磷酸三鉀;金屬氫化物,諸如氫化鋰、氫化鈉、氫化鉀;金屬醇鹽諸如甲醇鈉、乙醇鈉、三級丁醇鉀;或有機鹼,諸如三乙基胺、三丁基胺、N,N-二異丙基乙基胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯。相對於1 mol 化合物[X],所使用之鹼的量可在0至5 mol的範圍內適當選擇,較佳為0.1至2 mol。
可使用於此反應的溶劑的實例包括醚類,諸如二乙醚、甲基三級丁基醚、環戊基甲基醚、四氫呋喃、2-甲基四氫呋喃、1,4-二㗁烷、單甘醇二甲醚;芳香烴,諸如苯、甲苯、二甲苯、對稱三甲苯、氯苯;鹵代烴,諸如二氯甲烷、氯仿、1,2-二氯乙烷;非質子極性溶劑,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮;醇類,諸如甲醇、乙醇、2-丙醇、三級丁醇、2-甲氧乙醇;腈類,諸如乙腈及丙腈;脂肪烴,諸如戊烷、己烷、環己烷及庚烷;吡啶,諸如吡啶、甲吡啶及二甲吡啶;三級胺,諸如三乙胺及三丁胺;水或其之混合溶劑等。相對於1 mol的化合物[X],所使用之溶劑的量為0.1至1000公升,較佳為0.2至100公升。
當在此反應中使用催化劑時,該可使用的催化劑包括金屬或金屬鹽及作為配體的化合物。此類催化劑可在反應系統中(原位)由金屬或金屬鹽和作為後述的配體的化合物製備,或者可在反應系統外預先製備,然後再添加至反應系統中。催化劑可包含除金屬或金屬鹽及化合物配體之外的其他成分。金屬或金屬鹽之實例包括銅化合物,諸如金屬銅、乙酸銅(單價)、乙酸銅(雙價)、氧化銅(單價)、氧化銅(雙價)、氯化銅(單價)及碘化銅(單價);鈀化合物,諸如鈀碳、氯化鈀、硝酸鈀、乙酸鈀、雙(三苯基膦鈀二氯化物、四(三苯基膦)鈀、三(二亞芐基丙酮)二鈀等。配體之實例包括伸乙基二胺、N,N-二甲基伸乙基二胺、N,N'-二甲基伸乙基二胺、四甲基伸乙基二胺、2,2'-聯吡啶、1,10-啡啉、新亞銅試劑(neocuproine)、3,4,7,8-四甲基-1,10-啡啉、2,9-聯苯基-1,10-啡啉、4,7-聯苯基-1,10-啡啉、4,5-雙(聯苯基膦)-9,9-二甲基二苯并哌喃、三苯基膦、1,1'-雙(聯苯基膦)二茂鐵等,及其鹽。相對於1 mol的金屬或金屬鹽,金屬或金屬鹽與作為配體的化合物的組合可從0.1至10 mol的範圍內適當選擇,且較佳為1至4 mol的作為配體的化合物。相對於1 mol的化合物[X],所使用之催化劑的量以金屬或金屬鹽計可在0.001至10 mol的範圍內適當選擇,且較佳為0.01至5 mol。
此反應的反應溫度可選自0°C至反應體系中之回流溫度的範圍內的任意溫度。反應較佳在20°C至180℃的溫度範圍內進行。
雖然此反應的反應時間依據反應溫度、反應基質、反應量等而變化,但通常為10分鐘至24小時。
反應完成後,可藉由諸如將反應混合物加入水中並濾出沉澱的固體,或以有機溶劑萃取反應混合物然後濃縮的程序分離化合物[I]。若需要,分離的化合物[I]可藉由管柱層析、再結晶、蒸餾等進一步純化。
製造方法5
在本發明化合物之中,通式[XIV]代表的化合物可例如根據下例方法製造。
(其中,W
1、W
2、m、n、R
1、R
2、A
1、A
2、A
3、A
4、A
5、A
6、R
8、R
9及R
10具有如上述相同的含義。)
即,通式[XIV]代表的化合物可藉由在合適的溶劑中,於存在或不存在合適之鹼或合適之酸的情況下,使通式[XII]代表的化合物與通式[XIII]代表的化合物反應來製備。
相對於1 mol 化合物[XII],此反應中所使用之化合物[XIII]的量通常可在1至5 mol的範圍內適當選擇,較佳為1至2 mol。
當在此反應中使用鹼時,該可使用的鹼的實例包括鹼金屬氫氧化物,諸如氫氧化鋰、氫氧化鈉及氫氧化鉀;鹼土金屬氫氧化物,諸如氫氧化鈣及氫氧化鎂;鹼金屬碳酸鹽,諸如碳酸鋰、碳酸鈉、碳酸鉀及碳酸銫;鹼金屬碳酸氫鹽,諸如碳酸氫鈉及碳酸氫鉀;鹼金屬氟化物,諸如氟化鈉及氟化鉀;無機鹼,諸如磷酸三鉀;金屬氫化物,諸如氫化鋰、氫化鈉、氫化鉀;金屬醇鹽諸如甲醇鈉、乙醇鈉、三級丁醇鉀;或有機鹼,諸如三乙基胺、三丁基胺、N,N-二異丙基乙基胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯。相對於1 mol 化合物[XII],所使用之鹼的量可在0至5 mol的範圍內適當選擇,較佳為0至2 mol。
當在此反應中使用酸時,可使用的酸的實例包括無機酸,諸如氫氯酸、氫溴酸、硫酸、硝酸和磷酸,以及羧酸,諸如乙酸或三氟乙酸。相對於1 mol 化合物[XII],所使用之酸的量可在0至5 mol的範圍內適當選擇,較佳為0至2 mol。
可使用於此反應的溶劑的實例包括醚類,諸如二乙醚、甲基三級丁基醚、環戊基甲基醚、四氫呋喃、2-甲基四氫呋喃、1,4-二㗁烷、單甘醇二甲醚;芳香烴,諸如苯、甲苯、二甲苯、對稱三甲苯、氯苯;鹵代烴,諸如二氯甲烷、氯仿、1,2-二氯乙烷;非質子極性溶劑,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮;醇類,諸如甲醇、乙醇、2-丙醇、三級丁醇、2-甲氧乙醇;腈類,諸如乙腈及丙腈;脂肪烴,諸如戊烷、己烷、環己烷及庚烷;吡啶,諸如吡啶、甲吡啶及二甲吡啶;三級胺,諸如三乙胺及三丁胺;水或其之混合溶劑等。相對於1 mol的化合物[XII],所使用之溶劑的量為0.1至1000公升,較佳為0.2至100公升。
此反應的反應溫度可選自0°C至反應體系中之回流溫度的範圍內的任意溫度。反應較佳在20°C至100°C的溫度範圍內進行。
雖然此反應的反應時間依據反應溫度、反應基質、反應量等而變化,但通常為10分鐘至24小時。
反應完成後,可藉由諸如將反應混合物加入水中並濾出沉澱的固體,或以有機溶劑萃取反應混合物然後濃縮的程序分離化合物[XIV]。若需要,分離的化合物[XIV]可藉由管柱層析、再結晶、蒸餾等進一步純化。
製造方法6
在本發明化合物之中,通式[XVI]代表的化合物可例如根據下例方法製造。
(其中, m'表示0或1,n”表示1或2,m'和n”之和為1或2,W
1、W
2、R
1、R
2、A
1、A
2、A
3、A
4、A
5、A
6, A
7、A
8、A
9及R
10具有如上述相同的含義。)
即,通式[XVI]代表的化合物可藉由於存在或不存在合適之催化劑的情況下,在合適的溶劑中,使通式[XV]代表的化合物與合適的氧化劑反應來製備。
可使用於此反應的溶劑的實例包括芳香烴,諸如苯、甲苯、二甲苯、對稱三甲苯、氯苯;鹵代烴,諸如二氯甲烷、氯仿、1,2-二氯乙烷;非質子極性溶劑,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮;醇類,諸如甲醇、乙醇、2-丙醇、三級丁醇、2-甲氧乙醇;腈類,諸如乙腈及丙腈;脂肪烴,諸如戊烷、己烷、環己烷及庚烷;水或其之混合溶劑。相對於1 mol的化合物[XV],所使用之溶劑的量為0.1至1000公升,較佳為0.2至100公升。
可用於此反應的氧化劑的實例包括有機過氧化物,諸如間氯過氧苯甲酸、過氧甲酸、過氧乙酸或三氟過氧乙酸;無機過氧化物,諸如過氧化氫、過錳酸鉀、Oxone (註冊商標) (E.I. DuPont的商品名,含有過一硫酸氫鉀);鹵素含氧酸之鹽類,諸如過碘酸鈉或次氯酸鈉。相對於1 mol 化合物[XV],所使用之氧化劑的量可在0.5至5 mol的範圍內適當選擇,較佳為0.9至3 mol。
可用於此反應的催化劑的實例包括氯化釕(III)及其水合物、五氧化二釩、偏釩酸鈉、鎢酸鈉等。相對於1 mol 化合物[XV],所使用之催化劑的量可在0.001至10 mol的範圍內適當選擇,較佳為0.01至1 mol。
此反應的反應溫度可選自-78℃至反應體系中之回流溫度的範圍內的任意溫度。反應較佳在-10°C至100°C的溫度範圍內進行。
雖然此反應的反應時間依據反應溫度、反應基質、反應量等而變化,但通常為10分鐘至24小時。
反應完成後,可藉由諸如將反應混合物加入水中並濾出沉澱的固體,或以有機溶劑萃取反應混合物然後濃縮的程序分離化合物[XVI]。若需要,分離的化合物[XVI]可藉由管柱層析、再結晶、蒸餾等進一步純化。
製造方法7
在本發明化合物之中,通式[XIX]代表的化合物可例如根據下例方法製造。
(其中,n'代表0或1,且W
1、W
2、R
1、R
2、A
1、A
2、A
3、A
4、A
5、A
6、A
7、A
8、A
9及R
10具有如上述相同的含義。)
即,通式[XIX]代表的化合物可藉由在合適的溶劑中,於存在或不存在合適之鹼的情況下,使化合物[XVIII]或其鹽、化合物[XVII]及合適的氧化劑反應來製備。此外,此反應亦可在合適的催化劑存在下進行。
相對於1 mol 化合物[XVII],此反應中所使用之化合物[XVIII]的量通常可在1至100 mol的範圍內適當選擇,較佳為1至5 mol。
可用於此反應的氧化劑的實例包括鹵化劑,諸如氯、溴、碘、氯胺、N-氯琥珀醯亞胺(NCS)、N-溴琥珀醯亞胺(NBS)、N-碘琥珀醯亞胺(NIS)、1,3-二氯-5,5-二甲基乙內醯脲(DCH)、1,3-二溴-5,5-二甲基乙內醯脲(DBH)、1-溴-3-氯-5,5-二甲基乙內醯脲(BCDMH);及高價碘化合物,諸如(二氯碘)苯、(雙乙醯氧基碘)苯、(雙(三氟乙醯氧基)碘)苯、亞碘醯苯、氧碘基苯、2-氧碘基苯甲酸(IBX)、戴斯-馬丁氧化劑(Dess-Martin periodinane,DMP)、2-氧碘基苯磺酸(IBS)。相對於1 mol 化合物[XVII],所使用之氧化劑的量可在0.5至5 mol的範圍內適當選擇,較佳為0.9至3 mol。
當在此反應中使用鹼時,該可使用的鹼的實例包括鹼金屬氫氧化物,諸如氫氧化鋰、氫氧化鈉及氫氧化鉀;鹼土金屬氫氧化物,諸如氫氧化鈣及氫氧化鎂;鹼金屬碳酸鹽,諸如碳酸鋰、碳酸鈉、碳酸鉀及碳酸銫;鹼金屬碳酸氫鹽,諸如碳酸氫鈉及碳酸氫鉀;鹼金屬氟化物,諸如氟化鈉及氟化鉀;無機鹼,諸如磷酸三鉀、氧化鎂、氧化鋁;金屬氫化物,諸如氫化鋰、氫化鈉、氫化鉀;金屬醇鹽,諸如甲醇鈉、乙醇鈉、三級丁醇鉀;或有機鹼,諸如三乙胺、三丁胺、N,N-二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯。相對於1 mol之化合物[XVII],鹼的使用量可在0至20 mol的範圍內適當選擇,較佳為0至10 mol。
可使用於此反應的溶劑的實例包括醚類,諸如二乙醚、甲基三級丁基醚、環戊基甲基醚、四氫呋喃、2-甲基四氫呋喃、1,4-二㗁烷、單甘醇二甲醚;芳香烴,諸如苯、甲苯、二甲苯、對稱三甲苯、氯苯;鹵代烴,諸如二氯甲烷、氯仿、1,2-二氯乙烷;非質子極性溶劑,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮;醇類,諸如甲醇、乙醇、2-丙醇、三級丁醇、2-甲氧乙醇;腈類,諸如乙腈及丙腈;脂肪烴,諸如戊烷、己烷、環己烷及庚烷;吡啶,諸如吡啶、甲吡啶及二甲吡啶;三級胺,諸如三乙胺及三丁胺;水或其之混合溶劑等。相對於1 mol的化合物[XVII],所使用之溶劑的量為0.1至1000公升,較佳為0.2至100公升。
可用於此反應的催化劑的實例包括乙酸銠(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)],乙醯亞胺酸銠(II)等。相對於1 mol 化合物[XVII],所使用之催化劑的量可在0.001至10 mol的範圍內適當選擇,較佳為0.005至1 mol。
此反應的反應溫度可選自-78℃至反應體系中之回流溫度的範圍內的任意溫度。反應較佳在0℃至100°C的溫度範圍內進行。
雖然此反應的反應時間依據反應溫度、反應基質、反應量等而變化,但通常為10分鐘至48小時。
反應完成後,可藉由諸如將反應混合物加入水中並濾出沉澱的固體,或以有機溶劑萃取反應混合物然後濃縮的程序分離化合物[XIX]。若需要,分離的化合物[XIX]可藉由管柱層析、再結晶、蒸餾等進一步純化。
製造方法8
在本發明化合物之中,通式[XXI]代表的化合物可例如根據下例方法製造。
(其中,W
1、W
2、R
1、R
2、A
1、A
2、A
3、A
4、A
5、A
6、A
7、A
8、A
9及R
10具有如上述相同的含義。)
即,通式[XXI]代表的化合物可藉由在合適的溶劑中,於存在或不存在合適之鹼的情況下,使化合物[XVIII]或其鹽、化合物[XX]及合適的氧化劑反應來製備。此外,此反應亦可在合適的催化劑存在下進行。
相對於1 mol 化合物[XX],此反應中所使用之化合物[XVIII]的量通常可在1至100 mol的範圍內適當選擇,較佳為1至5 mol。
可用於此反應的氧化劑的實例包括鹵化劑,諸如氯、溴、碘、氯胺、N-氯琥珀醯亞胺(NCS)、N-溴琥珀醯亞胺(NBS)、N-碘琥珀醯亞胺(NIS)、1,3-二氯-5,5-二甲基乙內醯脲(DCH)、1,3-二溴-5,5-二甲基乙內醯脲(DBH)、1-溴-3-氯-5,5-二甲基乙內醯脲(BCDMH);及高價碘化合物,諸如(二氯碘)苯、(雙乙醯氧基碘)苯、(雙(三氟乙醯氧基)碘)苯、亞碘醯苯、氧碘基苯、2-氧碘基苯甲酸(IBX)、戴斯-馬丁氧化劑(DMP)、2-氧碘基苯磺酸(IBS)。相對於1 mol 化合物[XX],所使用之氧化劑的量可在0.5至5 mol的範圍內適當選擇,較佳為0.9至3 mol。
當在此反應中使用鹼時,該可使用的鹼的實例包括鹼金屬氫氧化物,諸如氫氧化鋰、氫氧化鈉及氫氧化鉀;鹼土金屬氫氧化物,諸如氫氧化鈣及氫氧化鎂;鹼金屬碳酸鹽,諸如碳酸鋰、碳酸鈉、碳酸鉀及碳酸銫;鹼金屬碳酸氫鹽,諸如碳酸氫鈉及碳酸氫鉀;鹼金屬氟化物,諸如氟化鈉及氟化鉀;無機鹼,諸如磷酸三鉀、氧化鎂、氧化鋁;金屬氫化物,諸如氫化鋰、氫化鈉、氫化鉀;金屬醇鹽,諸如甲醇鈉、乙醇鈉、三級丁醇鉀;或有機鹼,諸如三乙胺、三丁胺、N,N-二異丙基乙胺、N,N-二甲基苯胺、吡啶、2,6-二甲吡啶、4-N,N-二甲基胺基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一烯。相對於1 mol 化合物[XX],所使用之鹼的量可在0至20 mol的範圍內適當選擇,較佳為0至10 mol。
可使用於此反應的溶劑的實例包括醚類,諸如二乙醚、甲基三級丁基醚、環戊基甲基醚、四氫呋喃、2-甲基四氫呋喃、1,4-二㗁烷、單甘醇二甲醚;芳香烴,諸如苯、甲苯、二甲苯、對稱三甲苯、氯苯;鹵代烴,諸如二氯甲烷、氯仿、1,2-二氯乙烷;非質子極性溶劑,諸如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯啶酮、二甲亞碸、環丁碸、1,3-二甲基-2-咪唑啶酮;醇類,諸如甲醇、乙醇、2-丙醇、三級丁醇、2-甲氧乙醇;腈類,諸如乙腈及丙腈;脂肪烴,諸如戊烷、己烷、環己烷及庚烷;吡啶,諸如吡啶、甲吡啶及二甲吡啶;三級胺,諸如三乙胺及三丁胺;水或其之混合溶劑等。相對於1 mol的化合物[XX],所使用之溶劑的量為0.1至1000公升,較佳為0.2至100公升。
可用於此反應的催化劑的實例包括乙酸銠(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)]、乙醯亞胺酸銠(II)等。相對於1 mol 化合物[XX],所使用之催化劑的量可在0.001至10 mol的範圍內適當選擇,較佳為0.01至5 mol。
此反應的反應溫度可選自-78℃至反應體系中之回流溫度的範圍內的任意溫度。反應較佳在0℃至100°C的溫度範圍內進行。
雖然此反應的反應時間依據反應溫度、反應基質、反應量等而變化,但通常為10分鐘至48小時。
反應完成後,可藉由諸如將反應混合物加入水中並濾出沉澱的固體,或以有機溶劑萃取反應混合物然後濃縮的程序分離化合物[XXI]。若需要,分離的化合物[XXI]可藉由管柱層析、再結晶、蒸餾等進一步純化。
通式[II]及[IV]代表的本發明雜環化合物是在製備本發明之通式[I]代表的雜環化合物或其農業上可接受的鹽中作為中間體的有用化合物。
本發明的殺蟲劑組成物包含本發明通式[I]代表的雜環化合物或其農業上可接受的鹽作為活性成分。
如果需要,本發明的殺蟲劑組成物可包含通常用於殺蟲劑調配物的添加劑成分(載劑)。
本發明的害蟲防治劑包含本發明通式[I]代表的雜環化合物或其農業上可接受的鹽作為活性成分。本發明的害蟲防治劑通常是殺蟲劑、殺蟎劑及殺線蟲劑。
如果需要,本發明的害蟲防治劑可包含通常用於殺蟲劑調配物的添加劑成分(載劑)。
添加劑成分的實例包括載劑,諸如固體或液體載劑、表面活性劑、黏合劑、膠黏劑、增稠劑、著色劑、撒布劑、黏合撒布劑、抗凍劑、抗結塊劑、崩解劑、分解抑製劑等。另外,如果需要,亦可使用防腐劑、植物碎片等作為添加劑成分。此外,這些添加劑成分可單獨使用,亦可兩種以上組合使用。
固體載劑之實例包括礦物載劑,諸如葉蠟石黏土、高嶺土、矽石黏土、滑石、矽藻土、沸石、膨潤土、酸性黏土、活性黏土、阿塔帕石黏土(attapargas clay)、蛭石、波來鐵(pearlite)、浮石、白碳(合成矽酸、合成矽酸鹽等)、二氧化鈦;植物載劑,諸如木粉、玉米梗、核桃殼、果核、稻殼、鋸末、麥麩、大豆粉、粉狀纖維素、澱粉、糊精和糖;無機鹽載體,諸如碳酸鈣、硫酸銨、硫酸鈉、氯化鉀;高分子載劑,諸如聚乙烯、聚丙烯、聚氯乙烯、聚乙酸乙烯酯、乙烯-乙酸乙烯酯共聚物、脲醛樹脂。
液體載劑之實例包括一元醇,諸如甲醇、乙醇、丙醇、2-丙醇、丁醇及環己醇;多元醇,諸如乙二醇、二甘醇、丙二醇、己二醇、聚乙二醇、聚丙二醇及甘油;多元醇衍生物,諸如丙二醇醚;酮類,諸如丙酮、甲基乙基酮、甲基異丁基酮、二異丁基酮、環己酮和異佛酮(isophorone);醚類,諸如二乙醚、1,4-二㗁烷、賽珞蘇(cellosolve)、二丙醚及四氫呋喃;脂肪烴,諸如正烷烴、環烷烴、異鏈烷烴、煤油及礦物油;芳香烴,諸如甲苯、C
9-C
10烷基苯、二甲苯、溶劑油、烷基萘及高沸點芳香烴;鹵代烴,諸如1,2-二氯乙烷、氯仿及四氯化碳;酯類,諸如乙酸乙酯、酞酸二異丙酯、酞酸二丁酯、酞酸二辛酯及己二酸二甲酯;內酯類,諸如γ-丁內酯;醯胺類,諸如N,N-二甲基甲醯胺、N,N-二乙基甲醯胺、N,N-二甲基乙醯胺及N-甲基-2-吡咯啶酮;腈類,諸如乙腈;硫化合物,諸如二甲亞碸;植物油,諸如大豆油、菜籽油、棉籽油、棕櫚油和蓖麻油;及源自植物油的脂肪酸低級烷酯;水等。
表面活性劑之實例包括非離子表面活性劑,諸如山梨糖醇酐脂肪酸酯、聚氧乙烯山梨糖醇酐脂肪酸酯、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冷凝液、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、聚亞烷基苄基苯基醚、聚氧化烯苯乙烯基苯基醚、乙炔二醇、聚氧化烯加成乙炔二醇、聚氧乙烯醚型聚矽氧、酯型聚矽氧、氟表面活性劑、聚氧乙烯蓖麻油及聚氧乙烯氫化蓖麻油;陰離子表面活性劑,諸如硫酸烷酯、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、金屬磺酸鹽、磺基琥珀酸烷酯、萘磺酸鹽、烷基萘磺酸鹽、萘磺酸之福馬林冷凝液之鹽、烷基萘磺酸之福馬林冷凝液之鹽、脂肪酸鹽、聚羧酸鹽、N-甲基-脂肪酸肌胺酸鹽、樹脂酸鹽、聚氧乙烯烷基醚磷酸鹽及聚氧乙烯烷基苯基醚磷酸鹽;陽離子表面活性劑,諸如月桂基胺鹽酸鹽、硬脂胺鹽酸鹽、油胺鹽酸鹽、硬脂胺乙酸鹽、硬脂胺基丙基胺乙酸鹽、烷基三甲基銨氯及烷胺鹽,諸如烷基二甲基苄烷銨氯;兩性表面活性劑,諸如甜菜鹼型,如二烷基二胺基乙基甜菜鹼及烷基二甲基芐基甜菜鹼,及胺基酸型,如二烷基胺基乙基甘胺酸和烷基二甲基芐基甘胺酸等。
黏合劑及膠黏劑之實例包括羧甲基纖維素及其鹽類、糊精、水溶性澱粉、黃原膠、瓜爾膠(guar gum)、蔗糖、聚乙烯吡咯啶酮、阿拉伯膠、聚乙烯醇、聚乙酸乙烯酯、聚丙烯酸鈉、聚乙二醇、聚環氧乙烷、天然磷脂(例如,頭孢酸(cepharic acid)、卵磷脂等)等。
增稠劑之實例包括水溶性聚合物,諸如黃原膠、瓜爾膠、羧甲基纖維素、聚乙烯吡咯啶酮、羧乙烯基聚合物、丙烯酸聚合物、澱粉衍生物和多醣;無機細粉,諸如高純膨潤土、白炭;有機細粉,諸如有機膨潤土等。
著色劑之實例包括無機顏料,諸如氧化鐵、氧化鈦、普魯士藍(prussian blue);有機染料,諸如茜素染料、偶氮染料和金屬酞菁染料。
撒布劑之實例包括聚矽氧基表面活性劑、纖維素粉末、糊精、修飾澱粉、聚胺基羧酸螯合化合物、交聯聚乙烯吡咯啶酮、馬來酸/苯乙烯共聚物、甲基丙烯酸共聚物、多元醇聚合物與二羧酸酐之半酯、聚苯乙烯磺酸之水溶性鹽、聚氧乙烯鏈烷二醇、聚氧乙烯炔二醇、炔二醇等。
黏合撒布劑之實例包括各種表面活性劑,諸如二烷基磺基琥珀酸鈉、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯脂肪酸酯;石蠟、萜烯、聚醯胺樹脂、聚丙烯酸鹽、聚氧乙烯、蠟、聚乙烯烷基醚、烷基酚福爾馬林冷凝液、合成樹脂乳液等。
抗凍劑之實例包括多元醇類,諸如乙二醇、二甘醇、丙二醇和甘油。
抗結塊劑之實例包括多醣類,諸如澱粉、藻酸、甘露糖和半乳糖;聚乙烯吡咯啶酮、白碳、酯膠、石油樹脂等。
崩解劑之實例包括三聚磷酸鈉、六偏磷酸鈉、金屬硬脂酸鹽、纖維素粉末、糊精、甲基丙烯酸酯共聚物、聚乙烯吡咯啶酮、聚胺基羧酸螯合化合物、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。
分解抑製劑之實例包括乾燥劑,諸如沸石、生石灰和氧化鎂;抗氧化劑,諸如酚基、胺基、硫基、磷酸基抗氧化劑;UV吸收劑,諸如水楊酸基和二苯基酮基UV吸收劑。
防腐劑之實例包括山梨酸鉀、1,2-苯并噻唑-3 (2H)-酮等。
植物碎片的實例包括鋸末、棕櫚、玉米梗、煙梗等。
另一方面,當本發明的害蟲防治劑中含有上述添加劑成分時,對於諸如固體載劑或液體載劑之載劑它們的質量含量比例通常選自5%至95%的範圍,較佳為20至90%,表面活性劑的範圍為0.1%至30%,較佳為0.5至10%,其他添加劑的範圍為0.1至30%,較佳為0.5至10%。
使用時,本發明之害蟲防治劑可配製成任何劑型,例如,粉末、粉末顆粒、顆粒、可濕性粉劑、水溶性顆粒、水分散性顆粒、錠劑、速溶(jumbo)劑、乳化濃縮物、油、液體、懸浮濃縮物、乳劑、微乳劑、懸乳劑、微噴溶液、微膠囊、發煙劑、噴霧劑、餌劑、糊劑等。
在實際使用中,這些調配物可直接使用,或可在使用前以諸如水的稀釋劑稀釋至預定濃度。可藉由常用的施用方法進行含本發明化合物或其稀釋液的各種調配物的施用,諸如噴灑(例如噴灑、霧化、粉化、撒粉、撒粒、水面施用、盒內施用等)、土壤施用(例如混合、灌溉等)、表面施用(例如擦拭、粉末塗覆、覆蓋等)、種子處理(例如塗抹、粉末塗覆處理等)、浸泡、毒餌、煙霧施用等。此外,亦可將活性成分與草料混合來餵飼牲畜,以控制排泄物中害蟲的爆發和生長,特別是害蟲。
本發明的害蟲防治方法可藉由在上述施用方法中使用有效量的本發明通式[I]代表的雜環化合物或其農業上可接受的鹽的活性成分來進行。
本發明的害蟲防治劑中的活性成分的複合比(質量%)係依需要而適當選擇,例如在配製成粉末、粉末顆粒或微粒等情況下,在0.01~20%的範圍內,較佳為0.05~10%,在配製成顆粒等情況下,在0.1至30%的範圍內,較佳為0.5至20%,在配製成可濕性粉劑、水分散性顆粒等情況下,在1至70%的範圍內,較佳為5至50%,在配製成水溶性劑、液體等情況下,在1至 95%的範圍內,較佳為10至80%,在配製成乳化濃縮物等情況下,在5至90%的範圍內,較佳為10至80%,在配製成油等情況下,在1至50%的範圍內,較佳為5至30%,在配製成懸浮濃縮物等情況下,在5至60%的範圍內,較佳為10至50%,在配製成乳劑、微乳劑、懸乳劑等情況下,在5至70%的範圍內,較佳為10至60%,在配製成錠劑、餌劑、糊劑等情況下,在1至80%的範圍內,較佳為5至50%,在配製成發煙劑等情況下,在0.1至50%的範圍內,較佳為1至30%,且在配製成噴霧劑等情況下,在0.05至20%的範圍內,較佳為0.1至10%。
將這些調配物稀釋至適當濃度並噴灑或直接施用。
當用稀釋劑稀釋時,本發明的害蟲防治劑通常以0.1至5000 ppm的活性成分濃度施用。當以其原樣使用製劑時,每單位面積的施用量為每公頃0.1至5000 g活性成分化合物。然而,並不以此為限。
不待言明,本發明的害蟲防治劑即使單獨使用本發明化合物作為活性成分亦足夠有效。然而,如果需要,其可與其他肥料、農藥混合使用,諸如殺蟲劑、殺蟎劑、殺線蟲劑、增效劑、殺真菌劑、抗病毒劑、引誘劑、除草劑、植物生長調節劑等,其中可呈現出更佳的效果。
接著,以下舉例說明可混合或組合使用的已知殺蟲劑(殺蟲活性成分)、殺蟎劑(殺蟎活性成分)、殺線蟲劑(殺線蟲活性成分)和增效化合物(增效活性成分)。
殺蟲活性成分、殺蟎活性成分、殺線蟲活性成分及增效活性成分:
氟丙菊酯(acrinathrin)、印楝素(azadirachtin)、亞滅松(azamethiphos)、阿環那比(acynonapyr)、谷速松・乙基(azinphos-ethyl)、谷速松・甲基(azinphos-methyl)、滅蟎醌(acequinocyl)、亞滅培(acetamiprid)、乙醯蟲腈(acetoprole)、毆殺松(acephate)、亞環鍚(azocyclotin)、阿巴汀(abamectin)、雙丙環蟲酯(afidopyropen)、阿福索拉納(afoxolaner)、呋蟲胺(amidoflumet)、三亞蟎(amitraz)、棉鈴威(alanycarb)、得滅克(aldicarb)、碸滅威(aldoxycarb)、亞列寧(allethrin)[包含d-順-反-式、d-反-式]、依殺松(isazophos)、氯唑磷(isamidofos)、水胺硫磷(isocarbophos)、加福松(isoxathion)、抑克斯能(isocycloseram)、甲基亞芬松(isofenphos-methyl)、滅必蝨(isoprocarb)、ε-甲氧苄氟菊酯(epsilon-metofluthrin)、ε-沒氟菊酯(epsilon-momfluorothrin)、愛獲滅(ivermectin)、依米賽松(imicyafos)、益達胺(imidacloprid)、依普寧(imiprothrin)、因達匹(indazapyroxamet)、因得克(indoxacarb)、益化利(esfenvalerate)、愛芬克(ethiofencarb)、愛殺松(ethion)、益斯普(ethiprole)、二溴化乙烯(ethylene dibromide)、依殺蟎(etoxazole)、依芬寧(etofenprox)、滅線磷(ethoprophos)、益多松(etrimfos)、依馬菌素(emamectin)、因滅汀(emamectin benzoate)、安殺番(endosulfan)、益避寧(empenthrin)、噁唑硫非(oxazosulfyl)、歐殺滅(oxamyl)、滅多松(oxydemeton-methyl)、異亞碸磷(oxydeprofos)、毆滅松(omethoate)、核多角體病病毒(Nuclear polyhedrosis virus)、硫線磷(cadusafos)、κ-七氟菊酯(kappa-tefluthrin)、κ-畢芬寧(kappa-bifenthrin)、水黃皮素(karanjin)、培丹(cartap)、顆粒病病毒(Granulosis virus)、加保利(carbaryl)、丁基加保扶(carbosulfan)、加保扶(carbofuran)、γ-BHC(gamma-BHC)、滅殺威(xylylcarb)、拜裕松(quinalphos)、烯蟲炔酯(kinoprene)、蟎離丹(chinomethionat)、急性麻痺病病毒(Entero virus)、牛壁逃(coumaphos)、冰晶石(cryolite)、可尼丁(clothianidin)、克芬蟎(clofentezine)、可芬諾(chromafenozide)、氯蟲醯胺(chlorantraniliprole)、氯氧磷(chlorethoxyfos)、可氯丹(chlordane)、硝基三氯甲烷(chloropicrin)、陶斯松(chlorpyrifos)、陶斯松・甲基(chlorpyrifos-methyl)、克凡派(chlorfenapyr)、克芬松(chlorfenvinphos)、克福隆(chlorfluazuron)、氯甲硫磷(chlormephos)、氯普亞列寧(chloroprallethrin)、昆蟲痘病毒(Entomopoxi virus)、虹色病毒(Irido virus)、氰蟲醯胺(cyazypyr)、氰乃松(cyanophos)、汰芬隆(diafenthiuron)、二胺磷(diamidafos)、賽安勃(cyantraniliprole)、賽派芬(cyetpyrafen)、除蟎靈(dienochlor)、唑蟎氰(cyenopyrafen)、蔬果磷(dioxabenzofos)、二苯丙醚(diofenolan)、西格瑪病毒(Sigma virus)、環溴蟲醯胺(cyclaniliprole)、環氧蟲啶(cycloxaprid)、雙特氯松(dicrotophos)、除線磷(dichlofenthion)、環丁三氟喃(cyclobutrifluram)、乙氰菊酯(cycloprothrin)、二氯松(dichlorvos)、二氯滅嗪(dicloromezotiaz)、大克蟎(dicofol)、第昔尼(dicyclanil)、二硫松(disulfoton)、達特南(dinotefuran)、敵蟎通(dinobuton)、氯氟氰蟲醯胺(cyhalodiamide)、賽洛寧(cyhalothrin)[包含gamma-體,lambda-體]、賽芬寧(cyphenothrin)[包含(1R)-反-式]、賽扶寧(cyfluthrin)[包含β型]、二福隆(diflubenzuron)、賽芬蟎(cyflumetofen)、氟蟎嗪(diflovidazin)、環丙氟蟲胺(cyproflanilide)、鍚蟎丹(cyhexatin)、亞滅寧(cypermethrin)[包含α型、β型、θ型及ζ (zeta)型]、大普達井(dimpropyridaz)、二甲基-2,2,2-三氯-1-羥基乙基膦酸酯(DEP)、甲基毒蟲畏(dimethylvinphos)、大滅松(dimethoate)、四氟甲醚菊酯(dimefluthrin)、茉莉酮(jasmone)、順式-茉莉酮(cis-jasmone)、茉莉酸(jasmonic acid)、茉莉酸甲酯(methyl jasmonate)、矽護芬(silafluofen)、賽滅淨(cyromazine)、蟲生線蟲(Steinernema carpocapsae)、昆蟲寄生性線蟲(Steinernema kushidai)、格拉斯氏線蟲(Steinernema glaseri)、spidoxamat、賜諾特(spinetoram)、賜諾殺(spinosad)、賜派芬(spirodiclofen)、賜派滅((spirotetramat)、賜派酮(spiropidion)、螺甲蟎酯(spiromesifen)、蘇康脲鈉(sulcofuron-sodium)、氟蟲胺(sulfluramid)、速殺氟(sulfoxaflor)、治螟磷(sulfotep)、二嗪農(diazinon)、賽果培(thiacloprid)、賽速安(thiamethoxam)、替阿札芬(tioxazafen)、硫敵克(thiodicarb)、硫賜安(thiocyclam)、殺蟲雙(thiosultap)、治線磷(thionazin)、硫伐隆(thiofanox)、硫滅松(thiometon)、替克樂比薩佛(tyclopyrazoflor)、四氯蟲醯胺(tetrachlorantraniliprole)、樂本松(tetrachlorvinphos)、得脫蟎(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)、汰福寧(tefluthrin)、得福隆(teflubenzuron)、內吸磷・S・甲基(demeton-S-methyl)、亞培松(temephos)、第滅寧(deltamethrin)、托福松(terbufos)、泰滅寧(tralomethrin)、拜富寧(transfluthrin)、唑蚜威(triazamate)、三落松(triazophos)、三氯松(trichlorfon)、棘孢木黴菌(Trichoderma asperellum)、木黴菌(Trichoderma)、擬青黴菌(Paecilomyces)、哈氏木黴菌(Trichoderma harzianum)、三福隆(triflumuron)、三氟殺線酯(trifluenfuronate)、三氟苯嘧啶(triflumezopyrim)、混殺威(trimethacarb)、脫芬瑞(tolfenpyrad)、二溴磷(naled)、尼古丁(nicotine)、菸鹼氟脯(nicofluprole)、烯啶蟲胺(nitenpyram)、奈馬克丁(nemadetin)、濃核病病毒(Denso virus)、諾伐隆(novaluron)、諾福隆(noviflumuron)、淡紫色擬青黴(Paecilomyces lilacinus)、洋蔥假單胞菌(Barkholderia cepacia)、伯克氏菌(Barkholderia rinojensis)、臘蚧輪刺孢菌(Verticillium lecanii)、烯蟲乙酯(hydroprene)、西澤巴斯德氏菌(Pasteuria nishizawae)、穿透巴斯德芽孢菌(Pasteuria penetrans)、液化澱粉芽孢桿菌(Bacillus amyloliquefaciens)、堅強芽孢桿菌(Bacillus firmus)、球形芽孢桿菌(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)所生產之昆蟲毒素、蘇雲金芽孢桿菌 亞種 鮎澤(Bacillus thuringiensis subsp. Aizawai)、蘇雲金芽孢桿菌亞種 以色列(Bacillus thuringiensis subsp. Israelensis)、蘇雲金芽孢桿菌 亞種 庫斯克(Bacillus thuringiensis subsp. Kurstaki)、蘇雲金芽孢桿菌・亞種 擬步行蟲(Bacillus thuringiensis subsp. Tenebrionis)、日本甲蟲芽孢桿菌(Bacillus popilliae)、地衣芽孢桿菌(Bacillus licheniformis)、繁米松(vamidothion)、巴拉松(parathion)、巴拉松・甲基(parathion-methyl)、合芬寧(halfenprox)、氯蟲醯肼(halofenozide)、百亞列寧(bioallethrin)、百亞列寧S‐環戊烯基(bioallethrin S-cyclopentenyl)、百列滅寧(bioresmethrin)、雙-(2-氯-1-甲基乙基)醚(DCIP)、雙三氟蟲脲(bistrifluron)、海滅隆(hydramethylnon)、必芬蟎(bifenazate)、畢芬寧(bifenthrin)、氟蟲雙醯胺(pyflubumide)、胡椒基丁醚(piperonyl butoxide)、派滅淨(pymetrozine)、白克松(pyraclofos)、吡嗪氟蟲腈(pyrafluprole)、必芬松(pyridaphenthion)、畢達本(pyridaben)、三氟甲吡醚(pyridalyl)、百利福腙(pyrifluquinazon)、皮瑞普(pyriprole)、百利普芬(pyriproxyfen)、比加普(pirimicarb)、畢汰芬(pyrimidifen)、嘧蟎胺(pyriminostrobin)、亞特松(pirimiphos-methyl)、除蟲菊素(pyrethrine)、伐滅磷(famphur)、芬普尼(fipronil)、芬殺蟎(fenazaquin)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬諾克(fenoxycarb)、苯硫威(fenothiocarb)、酚丁滅寧(phenothrin)[包含(1R)-反-式]、仲丁威(fenobucarb)、芬殺松(fenthion)、賽達松(fenthoate)、芬化利(fenvalerate)、芬普蟎(fenpyroximate)、氧化芬佈賜(fenbutatin oxide)、芬普寧(fenpropathrin)、大福松(fonofos)、氟化硫醯(sulfuryl fluoride)、佈嘉信(butocarboxim)、丁酮威(butoxycarboxim)、普亞列寧(prallethrin)、嘧蟎酯(fluacrypyrim)、氯氟氰蟲醯胺(fluazaindolizine)、氟佐隆(fluazuron)、氟噻蟲碸(fluensulfone)、氟吡菌醯胺(fluopyram)、氟乙酸鈉鹽(sodium fluoroacetate)、氟米塔麥(fluxametamide)、氟環隆(flucycloxuron)、護賽寧(flucythrinate)、氟硫滅(flusulfamide)、賽扶寧(fluthrin)、福化利(fluvalinate)[包含τ (tau)型]、氟吡呋喃酮(flupyradifurone)、吡氟硫磷(flupyrazofos)、氟必靈(flupyrimin)、丁烯氟蟲腈(flufiprole)、福芬靈(flufenerim)、氟菌蟎酯(flufenoxystrobin)、氟芬隆(flufenoxuron)、氟殺逢(fluhexafon)、氟大滅(flubendiamide)、氟苯氟醚(flupentiofenox)、福滅寧(flumethrin)、氟拉蘭(fluralaner)、氣鈴芬(flurimfen)、普硫松(prothiofos)、氟蟲清(protrifenbute)、氟尼胺(flonicamid)、加護松(propaphos)、毆蟎多(propargite)、茉莉酸丙酯(prohydrojasmon)、佈飛松(profenofos)、布洛苯胺(broflanilide)、丙氟菊酯(profluthrin)、撲達松(propetamphos)、安丹(propoxur)、福美昆(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)、淡紫色擬青黴菌(Paecilomyces lilacinus)、啶菌噁唑(heptafluthrin)、飛達松(heptenophos)、百滅寧(permethrin)、異噻蟲唑(benclothiaz)、苯吡莫賽(benzpyrimoxan)、免速達(bensultap)、西脫蟎(benzoximate)、免敵克(bendiocarb)、免扶克(benfuracarb)、厚孢普可尼亞菌(Pochonia chlamydosporia)、纖細白僵菌(Beauveria tenella)、巴氏蠶白僵菌(Beauveria bassiana)、布氏白殭菌(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)、瀏陽霉素複合體(polynactins)、覆滅蟎(formetanate)、福瑞松(phorate)、機油(machine oil)、馬拉松(malathion)、密滅汀(milbemectin)、滅加松(mecarbam)、甲硫酚磷(mesulfenfos)、納乃得(methomyl)、聚乙醛(metaldehyde)、美氟綜(metaflumizone)、達馬松(methamidophos)、威百畝(metham)、滅賜克(methiocarb)、滅大松(methidathion)、異硫氰酸甲酯(methyl isothiocyanate)、甲基溴(methyl bromide)、氧氯甲氧氯(methoxychlor)、滅芬諾(methoxyfenozide)、甲醚菊酯(methothrin)、美特寧(metofluthrin)、美賜平(methoprene)、治滅蝨(metolcarb)、速滅磷(mevinphos)、氯氟醚菊酯(meperfluthrin)、植物單孢菌(Monacrosporium phymatophagum)、植物單孢菌(Monacrosporium phymatophagum)、亞速靈(monocrotophos)、沒氟菊酯(momfluorothrin)、哈氏木黴菌(Trichoderma harzianum)、性誘劑A(litlure-A)、性誘劑B(litlure-B)、磷化鋁(aluminium phosphide)、磷化鋅(zinc phosphide)、膦(phosphine)、祿芬隆(lufenuron)、列卡路(rescalure)、列滅寧(resmethrin)、雷皮菌素(lepimectin)、魚藤精(rotenone)、質型多角體病病毒包埋體(Cytoplasmic polyhedrosis virus)、芬佈賜(fenbutatin oxide)、石灰氮(calcium cyanide)、有機錫化合物(organotins)、硫酸尼古丁(nicotine-sulfate)、(Z)-11-十四碳烯基乙酸酯、(Z)-11-十六碳烯醛、(Z)-11-十六碳烯=乙酸酯、(Z)-9,12-十四烷二烯=乙酸酯、(Z)-9-十四碳烯-1-醇、(Z,E)-9,11-十四烷二烯=乙酸酯、(Z,E)-9,12-十四烷二烯=乙酸酯、1,1,1-三氯-2,2-雙(4-氯苯基)乙烷(DDT)、1,3‐二氯丙烯、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、CAS註冊編號:1472052-11-1)、2,4-二甲基-5-[6-(三氟甲硫基)己基氧基]苯基-2,2,2-三氟乙基 亞碸(化學名、CAS註冊編號:1472050-34-2)、2-{2-氟-4‐甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯氧基}-5-(三氟甲基)吡啶(化學名、CAS註冊編號:1448758-62-0)、3-氯-2-{2-氟-4‐甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯氧基}-5-(三氟甲基)吡啶(化學名、CAS註冊編號:1448761-28-1)、4,6-二硝基-o-甲酚(DNOC)、4-氟-2-甲基-5-(5,5-二甲基己基氧基]苯基 2,2,2-三氟乙基 亞碸(化學名、CAS註冊編號:1472047-71-4)、Bt蛋白質(Cry1Ab,Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb及Cry34/35Ab1)、甲基丁香油酚、4-(p-乙醯氧基苯基)-2-丁酮、(Z)-10-十四碳烯基=乙酸酯、(E,Z)-4,10-十四烷二烯=乙酸酯、(Z)-8-十二碳烯基=乙酸酯、(Z)-11-十四碳烯基=乙酸酯、(Z)-13-二十碳烯-10-酮、14-甲基-1-十八烯、AKD-1193(編碼編號)、BCS-AA10147(編碼編號)、CL900167(編碼編號)、NA-85 (編碼編號)、NI-30 (編碼編號)、O,O-二乙基-O-[4-(二甲基胺磺醯基)苯基]-硫代磷酸酯(DSP)、O-乙基-O-4-(硝基苯基)苯基硫代磷酸酯(EPN)、RU15525(編碼編號)、XMC(XMC)、Z-13-二十碳烯-10-酮、ZXI8901 (編碼編號)及F4260(編碼編號)。
接著,以下舉例說明可混合或組合使用的已知的除草劑化合物、除草活性成分或植物生長調節劑的化合物。然而,其並不以此為限。
除草劑化合物或除草活性成分:
碘苯腈(Ioxynil)(包括鋰鹽、鈉鹽、辛酸鹽等)、苯草醚(aclonifen)、丙烯醛(acrolein)、草芬定(azafenidin)、亞喜芬(acifluorfen)(包含與鈉鹽等)、四唑嘧磺隆(azimsulfuron)、磺草靈(asulam)、乙草胺(acetochlor)、草脫淨(atrazine)、莎稗磷(anilofos)、胺唑草酮(amicarbazone)、醯嘧磺隆(amidosulfuron)、殺草強(amitrole)、氯丙嘧啶酸(aminocyclopyrachlor)、氯胺吡啶酸(aminopyralid)、甲基胺草磷(amiprofos-methyl)、草殺淨(ametryn)、蘿摩花葉病毒(Araujia Mosaic Virus)、拉草(alachlor)、損毀鏈格孢(Alternaria destruens)、亞汰草(alloxydim)(包含鈉鹽等)、環丙嘧啶醇(ancymidol)、愛速隆(isouron)、依索氯托(isoxachlortole)、抑殺特(isoxaflutole)、異惡草胺(isoxaben)、異癸基醇乙氧基化物(Isodecylalkoholethoxylate)、異丙隆(isoproturon)、鹵苯胺唑(ipfencarbazone)、滅草喹(imazaquin)、甲咪唑烟酸(imazapic)(包含與胺之鹽等)、依滅草(imazapyr)(包含諸如異丙基胺鹽等)、咪草酸(imazamethabenz)、甲基咪草酸(imazamethabenz-methyl)、咪草啶酸(imazamox)、乙煙酸(imazethapyr)、依速隆(imazosulfuron)、吲嗪氟胺(indaziflam)、茚草酮(indanofan)、乙基甘草津(eglinazine-ethyl)、戊草丹(esprocarb)、甲基胺苯磺隆(ethametsulfuron-methyl)、抑伏靈(ethalfluralin)、磺噻隆(ethidimuron)、乙氧嘧磺隆(ethoxysulfuron)、氯氟草醚(ethoxyfen)、乙基氯氟草醚(ethoxyfen-ethyl)、乙氧草黃(ethofumesate)、乙氧苯草胺(etobenzanid)、epyrifenacil、草藻滅二鈉鹽(endothal-disodium)、樂滅草(oxadiazon)、快噁草酮(oxadiargyl)、歐克芬(oxaziclomefone)、環氧嘧磺隆(oxasulfuron)、復祿芬(oxyfluorfen)、歐拉靈(oryzalin)、老布達胡椒病毒(Obuda Pepper Virus)、嘧苯胺磺隆(orthosulfamuron)、坪草丹(orbencarb)、油酸(oleic acid)、苯酮唑(cafenstrole)、辛酸(caprylic acid)、癸酸(capric acid)、乙基克繁草(carfentrazone-ethyl)、特胺靈(karbutilate)、雙醯草胺(carbetamide)、快伏草(quizalofop)、乙基快伏草(quizalofop-ethyl)、乙基快伏草-P(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、野油菜黃單孢菌(Xanthomonas campestris)、莫克草(quinoclamine)、快克草(quinclorac)、氯甲喹啉酸(quinmerac)、檸檬酸(citric acid)、草隆(cumyluron)、氯醯草膦(clacyfos)、草甘膦(glyphosate)(包含鈉、鉀、胺、丙基胺、異丙基胺、銨、異丙基銨、胍、單乙醇胺、膽鹼、BAPMA(N,N-雙-(胺基丙基)甲基胺)、二甲基胺或三甲基硫鹽等鹽類)、草銨膦(glufosinate)(包含胺或鈉鹽等)、草銨膦-P(glufosinate-P)、草銨膦-P-鈉鹽、剋草同(clethodim)、炔草酸(clodinafop)、炔丙基炔草酯(clodinafop-propargyl)、畢克草(clopyralid)(包含單乙醇胺鹽)、可滅蹤(clomazone)、甲氧基護谷(chlomethoxyfen)、克普草(clomeprop)、甲基氯酯磺草(cloransulam-methyl)、克攔本(chloramben)、氯草敏(chloridazon)、豆磺隆(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、大克草(chlorthal-dimethyl)、草克樂(chlorthiamid)、氯醯亞胺(chlorphthalim)、甲基整形醇(chlorflurenol-methyl)、克普芬(chlorpropham)、滅落寧(chlorbromuron)、枯草龍(chloroxuron)、氯麥隆(chlorotoluron)、酮螺達(ketospiradox)(包含鈉、鈣或銨鹽等)、葫蘆炭疽刺盤孢菌(Colletotrichum orbiculare)、似膠黏孢炭疽刺盤孢菌(Colletotrichum gloeosporioides)、曲型炭疽病菌(Colletotrichum truncatum)、真菌植物病原體(Chondrostercum purpureum)、嘧啶肟草醚(saflufenacil)、假蒟亭鹼(sarmentine)、氰乃淨(cyanazine)、氰胺、氟硫草定(diuron)、乙基乙醯甲草胺(diethatyl-ethyl)、二氧嘧啶三酮(dioxopyritrione)、麥草畏(dicamba)(包含與胺、二乙胺、異丙胺、二甘醇胺、二甲銨、二醇胺、異丙銨、金胺、鉀、三乙醇胺(trollamine)、BAPMA (N,N-雙-(胺基丙基)甲基胺)、膽鹼、鈉或鋰等之鹽類,或酯類,諸如甲酯等)、環草敵(cycloate)、環殺草(cycloxydim)、雙氯磺草胺(diclosulam)、環丙嘧磺隆(cyclosulfamuron)、環吡寧(cyclopyranil)、環吡瑞莫(cyclopyrimorate)、敵草腈(dichlobenil)、禾草靈(dichlofop)、禾草靈・P・甲基(diclofop-P-methyl)、禾草靈・甲基(diclofop-methyl)、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸-P (包含與二甲基銨、鉀、鈉、膽鹼等之鹽類,或酯類,諸如丁氧乙酯、2-乙基己酯、異辛酯、甲酯等)、敵草快(diquat)、二溴敵草快(diquat dibromide)、氟硫草定(dithiopyr)、環草隆(siduron)、敵樂胺(dinitramine)、乙基環醯草酯(cinidon-ethyl)、西速隆(cinosulfuron)、特樂酚(dinoseb)(包括乙酸鹽)、特樂酯(dinoterb)、賽伏草(cyhalofop)、丁基賽伏草(cyhalofop-butyl)、環吡氟草酮(cypyrafluone)、雙苯醯草胺(diphenamid)、野燕枯(difenzoquat)、大伏肯(diflufenican)、大芬比(diflufenzopyr)、草滅淨(simazine)、dimesulfazet、大滅克(dimethachlor)、戊草津(dimethametryn)、汰草滅(dimethenamid)、汰草滅・P(dimethenamid-P)、西草淨(simetryn)、大滅普(dimepiperate)、大滅能(dimefuron)、螢光假單胞菌(Pseudomonas fluorescens)、環庚草醚(cinmethylin)、滅草靈(swep)、磺草酮(sulcotrione)、氟磺唑草胺(sulfentrazone)、草硫膦(sulfosate)、磺醯磺隆(sulfosulfuron)、甲基嘧磺隆(sulfometuron-methyl)、西殺草(sethoxydim)、Scelerothinia minor、特草定(terbacil)、香草隆(daimuron)、疥鏈黴菌素・A(thaxtomin A)、煙草微綠嵌紋病毒(Tobacco Mild Green Mosaic Tobamovirus)、煙草胞裂病毒(Tobacco Rattle Virus)、茅草枯(dalapon)、噻草啶(thiazopyr)、氟丙嘧草酯(tiafenacil)、唑酮磺吩酸(thiencarbazone)(包括鈉鹽及甲酯等)、仲草丹(tiocarbazil)、殺丹(thiobencarb)、噻二唑草胺(thidiazimin)、噻苯隆(thidiazuron)、噻吩磺隆(thifensulfuron)、噻黃隆(thifensulfuron-methyl)、甜菜安(desmedipham)、敵草淨(desmetryne)、特福披洛米(tetflupyrolimet)、欣克草(thenylchlor)、牧草胺(tebutam)、得匍隆(tebuthiuron)、得殺草(tepraloxydim)、特呋喃三酮(tefuryltrione)、草淨津(terbuthylazine)、特丁淨(terbutryn)、特丁通(terbumeton)、田寶三酮(tembotrione)、吡草磺(topramezone)、三甲苯草酮(tralkoxydim)、賽其爛(triaziflam)、醚苯磺隆(triasulfuron)、賽法猛(triafamone)、野麥畏(tri-allate)、草達津(trietazine)、三氯比(triclopyr)、丁氧乙基三氯比(triclopyr-butotyl)、三氯比・三乙基銨(triclopyr-triethylammonium)、三氟甲磺隆(tritosulfuron)、三唑磺草酮(tripyrasulfone)、三氟草嗪(trifludimoxazin)、甲基氟胺磺隆(triflusulfuron-methyl)、三福林(trifluralin)、三氟啶磺隆(trifloxysulfuron)(包括鈉鹽等)、甲基苯磺隆(tribenuron-methyl)、硝黃草酮(tolpyralate)、納得爛(naptalam)(包含與鈉鹽等)、萘普草(naproanilide)、敵草胺(napropamide)、敵草胺-M(napropamide-M)、煙嘧磺隆(nicosulfuron)、乳酸(lactic acid)、草不龍(neburon)、氟草敏(norflurazon)、伯克氏菌(Burkholderia rinojensis)、萬隆(vernolate)、巴拉刈(paraquat)、巴拉刈・二氯化物(paraquat dichloride)、氟氯吡啶酯(halauxifen)、氟氯吡啶酯・苄基(halauxifen-benzyl)、氟氯吡啶酯・甲基(halauxifen-methyl)、伯克氏菌、合氯氟(haloxyfop)、合氯氟・P (haloxyfop-P)、合氯氟・乙氧基乙酯(haloxyfop-etotyl)、合氯氟・P・甲基(haloxyfop-P-methyl)、鹵索芬(halosafen)、合速隆(halosulfuron-methyl)、畢克斯隆索(bixlozone)、畢克爛(picloram)(包括與二氯銨、三乙醇胺(trolamine)等之鹽類)、氟吡醯草胺(picolinafen)、雙環哌喃酮(bicyclopyrone)、雙草醚・鈉鹽(bispyribac-sodium)、唑啉草酯(pinoxaden)、雙唑草酮(bipyrazone)、治草醚(bifenox)、哌草磷(piperophos)、雙唑草腈(pyraclonil)、磺醯草吡唑(pyrasulfotole)、匹唑芬(pyrazoxyfen)、乙基百速隆(pyrazosulfuron-ethyl)、苄草唑(pyrazolynate)、畢拉草(bilanafos)、派芬草(pyraflufen)、乙基派芬草(pyraflufen-ethyl)、噠草福(pyridafol)、嘧硫草醚・鈉鹽(pyrithiobac-sodium)、必汰草(pyridate)、環酯草醚(pyriftalid)、稗草丹(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、嘧啶硫蕃(pyrimisulfan)、甲基嘧草醚(pyriminobac-methyl)、派羅克殺草碸(pyroxasulfone)、吡唑磺草胺(pyroxsulam)、棕櫚疫黴(Phytophthora palmivora)、棉胺寧(phenisopham)、非草隆(fenuron)、異噁苯碸(fenoxasulfone)、噁唑菌胺(fenoxaprop)(包含甲基、乙基、異丙基酯)、噁唑菌胺・P(fenoxaprop-P)(包括甲酯、乙酯、異丙酯)、芬昆諾三酮(fenquinotrione)、乙基唑禾草酸(fenthiaprop-ethyl)、四唑醯草胺(fentrazamide)、苯唑氟草酮(fenpyrazone)、甜菜寧(phenmedipham)、Phoma chenopodicola、莖點黴菌(Phoma herbarum)、巨口莖點黴菌(Phoma macrostoma)、丁基拉草(butachlor)、布芬草(butafenacil)、抑草磷(butamifos)、丁酯(butylate)、縱溝柄鏽菌(Puccinia canaliculata)、遏藍菜柄鏽菌(Puccinia thlaspeos)、丁烯草胺(butenachlor)、仲丁靈(butralin)、丁苯草酮(butroxydim)、啶嘧磺隆(flazasulfuron)、麥草伏(flamprop)(包括甲酯、乙酯、異丙酯)、麥草伏・M (flamprop-M)(包含甲酯、乙酯、異丙酯)、氟嘧磺隆(primisulfuron)、甲基氟嘧磺隆(primisulfuron-methyl)、伏寄普丁酯(fluazifop-butyl)、伏寄普・P(fluazifop-P)、伏寄普・P・丁酯、異丙吡草酯(fluazolate)、伏草隆(fluometuron)、乙基乙羧氟草醚(fluoroglycofen-ethyl)、氟酮磺隆・鈉鹽(flucarbazone-sodium)、氟消草(fluchloralin)、氟吡磺隆(flucetosulfuron)、氟噻甲草酯(fluthiacet-methyl)、氟啶嘧磺隆・甲基(flupyrsulfuron-methyl)(包含鈉、鈣或銨鹽等)、噻草胺(flufenacet)、氟噠嗪草酯(flufenpyr-ethyl)、四氟丙酸(flupropanate)(包含鈉鹽)、氟胺草唑(flupoxame)、丙炔氟草胺(flumioxazin)、氟胺草酯(flumiclorac-pentyl)、唑嘧磺草胺(flumetsulam)、氟啶草酮(fluridone)、呋草酮(flurtamone)、氯氟吡氧乙酸(fluroxypyr)(包含丁氧基丙酯、異辛酯類,或鈉、鈣、銨鹽等)、氟咯草酮(flurochloridone)、普拉草(pretilachlor)、丙苯磺隆(procarbazone)(包含與鈉鹽等)、氨氟樂靈(prodiamine)、三氟丙磺隆(prosulfuron)、苄草丹(prosulfocarb)、普拔草(propaquizafop)、撲草胺(propachlor)、普拔根(propazine)、除草靈(propanil)、戊炔草胺(propyzamide)、普樂寶(propisochlor)、咪唑嘧磺隆(propyrisulfuron)、苯胺靈(propham)、氟唑草胺(profluazol)、調環酸・鈣鹽(prohexadione-calcium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆・鈉鹽(propoxycarbazone-sodium)、氯苯噻草酮(profoxydim)、克草(bromacil)、溴莠敏(brompyrazon)、佈滅淨(prometryn)、撲滅通(prometon)、溴苯腈(bromoxynil)(包含丁酸、辛酸或庚酸等之酯類)、溴酚肟(bromofenoxim)、溴丁醯草胺(bromobutide)、雙氟磺草胺(florasulam)、氯氟吡啶酯(florpyrauxifen)、氯氟吡啶酯・苄基(florpyrauxifen-benzyl)、菲殺淨(hexazinone)、烯草胺(pethoxamid)、草除靈(benazolin)、草除靈・乙基(benazolin-ethyl)、平速爛(penoxsulam)、香瓜茄嵌紋病毒(Pepino Mosaic Virus)、胺苯吡菌酮(heptamaloxyloglucan)、氟丁醯草胺(beflubutamid)、氟丁醯草胺-M(beflubutamid-M)、克草猛(pebulate)、壬酸(pelargonic acid)、醯苯草酮(bencarbazone)、喹草酮(benquitrione)、雙苯嘧草酮(benzfendizone)、地散磷(bensulide)、免速隆(bensulfuron)、甲基免速隆、苯并雙環酮(benzobicyclon)、吡草酮(benzofenap)、本達隆(bentazone)、甲氯醯草胺(pentanochlor)、施得圃(pendimethalin)、本特松(pentoxazone)、氟草胺(benfluralin)、呋草黃(benfuresate)、殺木膦(fosamine)、氟磺胺(fomesafen)、甲醯嘧磺隆(foramsulfuron)、福芬素(forchlorfenuron)、甲氯丙酸(mecoprop)(包括鈉、鉀、異丙胺、三乙醇胺、二甲胺、二醇胺、三乙醇胺、膽鹼等鹽類,或乙二酯、2-乙基己酯、異辛酯、甲酯等酯類)、甲氯丙酸・P・鉀鹽(mecoprop-P-potassium)、磺胺磺隆(mesosulfuron)(包括甲酯等)、硝草酮(mesotrione)、滅草胺(metazachlor)、雙醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、苯嗪草酮(metamitron)、甲氯丙酸(metamifop)、威百畝(metam)(包含鈉鹽等)、甲烷亞砷酸二鈉(DSMA)、美西除靈(methiozolin)、甲基香草隆(methyldymuron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲基磺隆(metsulfuron-methyl)、撲多草(metobromuron)、吡喃隆(metobenzuron)、莫多草淨(metolachlor)、滅必淨(metribuzin)、甲哌啶氯化物(mepiquat chloride)、滅芬草(mefenacet)、單嘧磺隆(monosulfuron)(包括甲酯、乙酯、異丙酯)、綠谷龍(monolinuron)、稻得壯(molinate)、碘甲磺隆(iodosulfuron)、碘甲磺隆甲基鈉鹽(iodosulfulon-methyl-sodium)、碘芬磺隆(iofensulfuron)、碘芬磺隆・鈉鹽(iofensulfuron-sodium)、乳氟禾草靈(lactofen)、朗剋三酮(lancotrione)、理有龍(linuron)、rimisoxafen、碸嘧磺隆(rimsulfuron)、環草定(lenacil)、2,2,2-三氯乙酸(TCA)(包含鈉、鈣或銨鹽等)、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)(包括胺、二乙胺、三乙醇胺、異丙胺、二甲銨、二醇胺、十二烷基銨、庚基銨、十四烷基銨、三乙基銨、參(2-羥基丙基)銨、三乙醇胺(trolamine)、膽鹼、鈉或鋰等之鹽類,或酯類,諸如丁氧乙酯、2-丁氧基丙酯、2-乙基己酯、甲酯、乙酯、丁酯、異丁酯、辛酯、戊酯、丙酯、異辛酯、異丙酯、異辛酯、糠基酯等)、2,4-二氯苯氧基丁酸(2,4-DB)(包括胺、二乙胺、三乙醇胺、異丙胺、二甲銨、膽鹼、鈉或鋰等鹽類,或酯類,諸如異辛酯)、2-胺基-3-氯-1,4-萘醌(ACN)、2-甲基-4-氯苯氧基乙酸(MCPA)(包括鈉、二甲基銨、膽鹼等鹽類,或酯類,諸如2-乙基己酯、異辛酯、乙酯等)、2-甲基-4-氯苯氧基丁酸(MCPB)(包括鈉鹽及乙酯等)、4-(2,4-二氯苯氧基)丁酸(2,4-DB)、4,6-二硝基-O-甲酚(DNOC)(包括胺或鈉鹽等)、(5S)-3-(3,5-二氟苯基)-N-[rel-(3R,5R)-5-(三氟甲基磺醯基胺基甲醯基)四氫呋喃-3-基]-5-乙烯基-4H-異㗁唑-5-甲醯胺(化學名、CAS註冊編號:2266183-40-6) (國際公開號2018/228986、國際公開號2020/114934)、N4-(2,6-二氟苯基)-6-(1-氟-1-甲基乙基)-1,3,5-三𠯤-2,4-二胺(化學名、CAS註冊編號:1606999-43-2)(國際公開號2014/064094、國際公開號2015/162164)、(5S)-3-(3,5-二氟苯基)-N-[(3R)-5-(甲基磺醯基胺基甲醯基)-2,3-二氫呋喃-3-基]-5-乙烯基-4H-異㗁唑-5-甲醯胺(化學名、CAS註冊編號:2266190-06-9)(國際公開號2018/228986、國際公開號2020/114934)、(5R)-3-(3,5-二氟苯基)-5-甲基-N-[rel-(3R,5R)-5-(甲基磺醯基胺基甲醯基)四氫呋喃-3-基]-4H-異㗁唑-5-甲醯胺(化學名、CAS註冊編號:2266164-36-5)(國際公開號2018/228986、國際公開號2020/114934)、(5R)-3-(3,5-二氟苯基)-N-[(3R)-5-(甲氧基胺基甲醯基)-2,3-二氫呋喃-3-基]-5-甲基-4H-異㗁唑-5-甲醯胺(化學名、CAS註冊編號:2266170-31-2)(國際公開號2018/228986、國際公開號2020/114934)、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-側氧基-嗒𠯤-4-羰基]環己烷-1,3-二酮(化學名、CAS註冊編號:2138855-12-4)(國際公開號2017/178582、國際公開號2018/015476)、4-羥基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉啶-2-酮(化學名、CAS註冊編號:1708087-22-2)(國際公開號2015/059262、國際公開號2018/015476)、6-(1-氟環戊基)-N4-(2,3,5,6-四氟苯基)-1,3,5-三嗪-2,4-二胺 (化學名、CAS註冊編號:1820807-75-7)(國際公開第2015/162164號公報)、6-(1-氟-1-甲基-乙基)-N4-(2,3,5,6-四氟苯基)-1,3,5-三𠯤-2,4-二胺(化學名、CAS註冊編號:1606999-21-6)(國際公開號2014/064094、國際公開號2015/162164)、(5S)-3-(3-氟-5-甲基苯基)-N-[rel-(3R,5R)-5-(甲氧基胺基甲醯基)四氫呋喃-3-基]-5-乙烯基-4H-異㗁唑-5-甲醯胺(化學名、CAS註冊編號:2266292-43-5)(國際公開號2018/228986、國際公開號2020/114934)、6-(1-甲基環丁基)-N4-(2,3,5,6-四氟苯基)-1,3,5-三𠯤-4,4-二胺(化學名、CAS註冊編號:1607001-97-7)(國際公開號2014/064094、國際公開號2015/162164)、AE-F‐150944(編碼編號)、F9960(編碼編號)、IR-6396(編碼編號)、MCPA-硫代乙基、NC-656(編碼編號)、SYP-298(編碼編號)、SYP-300(編碼編號)、S-乙基二丙基硫胺甲酸酯(EPTC)、S-莫多草淨(S-metolachlor)、S-9750(編碼編號)、MSMA(MSMA)及HW-02(編碼編號)。
植物生長調節劑:
1-萘基乙醯胺、1-甲基環丙烯、1,3-二苯基脲、2,3,5-三碘苯甲酸、2-甲基-4-氯苯氧基丁酸(MCPB)[包含鈉鹽、乙酯等]、2-(萘-1-基)乙醯胺、2,6-二異丙基萘、3-[(6-氯-4-苯基喹唑啉-2-基)胺基]丙烷-1-醇、4-側氧基-4-(2-苯基乙基)胺基丁酸(化學名、CAS註冊編號:1083-55-2)、4-氯苯氧基乙酸(4-CPA)、5-胺基乙醯丙酸鹽酸鹽、5-(三氟甲基)苯并[b]噻吩-2-羧酸甲酯、AVG (胺基乙氧基乙烯基甘胺酸;aminoethoxyvinylglycine)、正癸醇、安希夫林(anisiflupurin)、四稀雌酮(aviglycine)、環丙嘧啶醇(ancymidol)、離層酸(abscisic acid)、亞賜圃(isoprothiolane)、依納素(inabenfide)、吲哚乙酸、吲哚丁酸、單克素(uniconazole)、單克素-P、Ecolyst、吲唑酯(ethychlozate)、益收生長素(ethephon)、丙醯藝苔素內酯(epocholeone)、氯化鈣、氯化膽鹼、羥喹啉硫酸鹽(oxine-sulfate)、opabactin、裂殖素(kinetin)、過氧化鈣、香旱芹酮(carvone)、喹喔啉(quinabactin)、甲酸鈣、坐果酸(cloxyfonac)、坐果酸・鉀鹽(cloxyfonac-potassium)、果美生長素(cloprop)、克美素(chlormequat)、克美素・氯化物(chlormequat-chloride)、克普芬(chlorpropham)、膽鹼、細胞分裂素(cytokinins)、氧化型穀胱甘肽(oxydized glutathione)、氰胺(cyanamide)、氰酸鈉、環苯胺(cyclanilide)、2,4-滴丙酸(dichlorprop)(包括二甲基銨、鉀、鈉及膽鹼鹽等,或酯類,諸如丁氧乙酯、2-乙基己酯、異辛酯、甲酯等)、2,4-滴丙酸-P (包括鈉、鉀、二甲基銨鹽等,或2-乙基己酯等)、敵草快(diquat)、二溴敵草快、環丙醯草胺(dikegulac)、激勃酸(gibberellinic acid)、勃激素A4(gibberellin A4)、勃激素A7、穫萎得(dimethipin)、殺雄啉(sintofen)、茉莉酮(jasmone)、順式-茉莉酮(cis-jasmone)、茉莉酸(jasmonic acid)、茉莉酸甲酯、鏈黴素(streptomycin)、石灰硫(calcium polysulfide)、亞拉生長素(daminozide)、碳酸鈣、噻苯隆(thidiazuron)、癸烷-1-醇、三十醇(triacontanol)、抑芽唑(triapenthenol)、抗倒酯(trinexapac-ethyl)、脫葉磷(tribufos)、巴克素(paclobutrazol)、石蠟(paraffin)、雙草醚・鈉鹽(bispyribac-sodium)、殺紋寧(hymexazol)、仲丁靈(butralin)、氟噻甲草酯(fluthiacet-methyl)、乙基派芬草(pyraflufen-ethyl)、氟節胺(flumetralin)、調嘧醇(flurprimidol)、芴丁酸(flurenol)、前尼替丁(pronitridine)、茉莉酸丙酯(prohydrojasmon)、調環酸・鈣鹽(prohexadione-calcium)、胺苯吡菌酮(heptamaloxyloglucan)、6-苄基胺基嘌呤、施得圃(pendimethalin)、福芬素(forchlorfenuron)、刺芒柄花素(formononetin)、馬來酸二醯肼(maleic hydrazide)、甲哌啶氯化物(mepiquat chloride)、美福泰(mefluidide)、脂殼寡糖(lipochitooligosaccharides) (諸如脂殼寡糖SP104)、硫化鈣。
接著,舉例說明可混合或組合使用的用於減少化學損傷的已知化合物。
減少化學損傷的化合物:
雙苯㗁唑酸(isoxadifen)、雙苯㗁唑酸・乙基、解草腈(oxabetrinil)、辛烷-1,8-二胺、解毒喹(cloquintocet)、解草酯(cloquintcet-mexyl)、二狄烈(dietholate)、解草胺腈(cyometrinil)、烯丙醯草胺(dichlormid)、二環酮(dicyclonone)、賽普磺胺(cyprosulfamide)、香草隆(daimuron)、萘酸酐(1,8-Naphthalic Anhydride)、解草唑(fenchlorazole)、解草唑乙酯(fenchlorazole-O-ethyl)、解草啶(fenclorim)、解草噁唑(furilazole)、氟草肟(fluxofenim)、解草胺(flurazole)、解草嗪(benoxacor)、美卡芬(metcamifen)、米芬能(mephenate)、吡唑二酸(mefenpyr)、吡唑二酸乙基、吡唑二酸-二乙基、低級烷基取代苯甲酸、2,2-二氯-N-(1,3-二氧戊烷-2-基甲基)-N-(2-丙烯基)乙醯胺(PPG-1292)、2-二氯甲基-2-甲基-1,3-二㗁烷(MG-191)、3-二氯乙醯基-2,2,5-三甲基-1,3-㗁唑烷(R-29148)、4-二氯乙醯基-1-氧雜-4-氮雜螺環[4.5]癸烷(AD-67)、4-羧基-3,4-二氫-2H-1-苯并吡喃-4-乙酸(CL-304415、編碼編號)、MON4660(編碼編號)、美卡芬(metcamifen)、N1,N2-二烯丙基-N2-二氯乙醯基甘胺酸醯胺(DKA-24、編碼編號)、1-溴-4-[(氯甲基)磺醯基]苯(CSB)、1-氧雜-4-氮雜螺環[4,5]癸烷-4-二硫代甲酸2-丙烯酯(Carbodithioate)(MG-838、編碼編號)、3-(二氯乙醯基)-2,2-二甲基-1,3-㗁唑烷(R-28725、編碼編號)、R-29148(編碼編號)、1-(二氯乙醯基)氮雜烷(TI-35、編碼編號)。
接著,以下舉例說明可混合或組合使用的殺菌劑(殺菌活性成分)或病害防治劑的化合物。
殺菌活性成分或病害防治劑之化合物:
放射形農桿菌(Agrobacterim radiobacter)、戊環唑(azaconazole)、阿拉酸式苯・S・甲基(acibenzolar-S-methyl)、嘧菌酯(azoxystrobin)、敵菌靈(anilazine)、安美速(amisulbrom)、胺基吡芬(aminopyrifen)、愛特丁(ametoctradin)、殺螟丹(aldimorph)、亞汰尼(isotianil)、吡唑萘菌胺(isopyrazam)、異丙噻菌胺(isofetamid)、異氟西波(isoflucypram)、亞賜圃(isoprothiolane)、種菌唑(ipconazole)、艾氟芬喹啉(ipflufenoquin)、抑氟康唑(ipfentrifluconazole)、依普同(iprodione)、抑發利(iprovalicarb)、丙基喜樂松(iprobenfos)、依滅列(imazalil)、克熱淨烷苯磺酸鹽(iminoctadine-albesilate)、克熱淨三乙酸鹽(iminoctadine-triacetate)、易胺座(imibenconazole)、應吡福安(inpyrfluxam)、應普馬汀A(imprimatin A)、應普馬汀B(imprimatin B)、護粒松(edifenphos)、乙環唑(etaconazole)、噻唑菌胺(ethaboxam)、依瑞莫菌胺(ethirimol)、乙氧基喹啉(ethoxyquin)、依得利(etridiazole)、烯髒菌酯(enestroburin)、烯肟菌酯(enoxastrobin)、依普座(epoxiconazole)、有機油(organic oils)、毆殺斯(oxadixyl)、噁嗪拉唑(oxazinylazole)、奧賽普林(oxathiapiprolin)、嘉保信(oxycarboxin)、氧喹啉銅(oxine-copper)、氧四環素(oxytetracycline)、噁咪唑反丁烯二酸鹽(oxpoconazole-fumarate)、歐索林酸(oxolinic acid)、辛酸銅(copper dioctanoate)、辛噻酮(octhilinone)、甲呋醯胺(ofurace)、肟醚菌胺(orysastrobin)、鄰苯基酚(o-phenylphenol)、嘉賜黴素(kasugamycin)、四氯丹(captafol)、加普胺(carpropamid)、貝芬替(carbendazim)、萎鏽靈(carboxin)、香旱芹酮(carvone)、假絲酵母(Candida oleophila)、佐氏假絲酵母(Candida saitoana)、快諾芬(quinoxyfen)、昆諾浮美林(quinofumelin)、蟎離丹(chinomethionat)、克菌丹(captan)、氟喹唑(quinconazole)、五氯硝基苯(quintozene)、克熱淨(guazatine)、鋅錳(cufraneb)、甲香菌酯(coumethoxystrobin)、丁香菌酯(coumoxystrobin)、鏈孢黏帚黴菌(Gliocradium catenulatum)、白色隱球酵母孢菌(Cryptococcus albidus)、克收欣(kresoxim-methyl)、克拉康(clozylacon)、粉紅螺旋聚孢霉(Clonostachys rosea)、乙菌利(chlozolinate)、氯吲哚醯肼(chloroinconazide)、四氯異苯(chlorothalonil)、地茂散(chloroneb)、毛殼菌(Chaetomium cupreum)、微坦盾殼黴(Coniothyrium minitans)、賽座滅(cyazofamid)、乙黴威(diethofencarb)、雙氯氰菌胺(diclocymet)、益發靈(dichlofluanid)、二氯苯賽斯(dichlobentiazox)、達滅淨(diclomezine)、大克爛(dicloran)、二氯酚(dichlorophen)、腈硫醌(dithianon)、達克利(diniconazole)、達克利・M(diniconazole-M)、鋅乃浦(zineb)、敵蟎普(dinocap)、大芬滅替(dipymetitrone)、二苯基胺(diphenylamine)、待克利(difenoconazole)、環氟菌胺(cyflufenamid)、二氟林(diflumetorim)、環克座(cyproconazole)、賽普洛(cyprodinil)、矽氟唑(simeconazole)、二甲嘧酚(dimethirimol)、二甲基二硫化物(dimethyl disulfide)、達滅芬(dimethomorph)、克絕(cymoxanil)、醚菌胺(dimoxystrobin)、絮絨擬酵母(Pseudozyma flocculosa)、致金黃色假單胞菌(Pseudomonas aureofaciens)、綠針假單胞菌(Pseudomonas chlororaphis)、丁香假單胞菌(Pseudomonas syringae)、螢光假單胞菌(Pseudomonas flurorescens)、羅氏假單胞菌(Pseudomonas rhodesiae)、福美鋅(ziram)、矽噻菌胺(silthiofam)、夏南瓜黃斑鑲嵌病毒弱毒株(Zucchini yellow mosaic virus)、鏈黴素(streptomycin)、灰綠鏈黴菌(Streptomyces griseoviridis)、鏈黴菌(Streptomyces lygicus)、螺噁茂胺(spiroxamine)、環丙吡菌胺(sedaxane)、辛菌胺(seboctylamine)、座賽胺(zoxamide)、苯并烯氟菌唑(solatenol)、邁隆(dazomet)、大孢籃狀菌(Talaromyces flavus)、噻醯菌胺(tiadinil)、腐絕(thiabendazole)、得恩地(thiram)、多保淨(thiophanate)、甲基多保淨(thiophanate-methyl)、賽氟滅(thifluzamide)、得恩地(thiram)、四氯硝基苯(tecnazene)、克枯爛(tecloftalam)、四克利(tetraconazole)、咪菌威(debacarb)、得克利(tebuconazole)、異丁乙氧喹啉(tebufloquin)、特比萘芬(terbinafine)、多果定(dodine)、嗎菌靈(dodemorph)、三泰隆(triadimenol)、三泰芬(triadimefon)、三挫磷(triazoxide)、水楊菌胺(trichlamide)、三環吡菌威(triclopyricarb)、棘孢木黴菌 (Trichoderma asperellum)、深綠木黴(Trichoderma atroviride)、蓋氏木黴(Trichoderma gamsii)、子座木黴(Trichoderma stromaticum)、青木黴(Trichoderma paecilomyces)、哈氏拉法木黴(Trichoderma harzianum)、綠木黴(Trichoderma viride)、青綠木黴(Trichoderma virens)、多孢木黴(Trichoderma polysporum)、哈茨木黴(Trichoderma harzianum rifai)、木素木黴(Trichoderma lignorum)、三賽唑(tricyclazole)、滅菌唑(triticonazole)、三得芬(tridemorph)、賽福座(triflumizole)、三氟敏(trifloxystrobin)、賽福寧(triforine)、托福寧(tolylfluanid)、脫克松(tolclofos-methyl)、甲磺菌胺(tolnifanide)、托普洛卡(tolprocarb)、代森鈉(nabam)、鏈黴菌素(natamycin)、萘替芬(naftifine)、氯啶(nitrapyrin)、酞菌酯(nitrothal-isopropyl)、尼瑞莫(nuarimol)、壬基酚磺酸銅(copper nonyl phenol sulphonate)、多黏類芽孢桿菌(Paenibacillus polymyxa)、洋蔥假單胞菌(Barkholderia cepacia)、液化澱粉芽孢桿菌(Bacillus amyloliquefaciens)、簡單芽孢桿菌(Bacillus simplex)、枯草芽孢桿菌(Bacillus subtilis)、短小芽胞桿菌(Bacillus pumilus)、地衣芽孢桿菌(Bacillus licheniformis)、免疫球蛋白(harpin protein)、爭論貪嗜菌(Variovorax paradoxus)、維利黴素(validamycin)、氯氟氰菊酯(valifenalate)、成團泛菌(Pantoea agglomerans)、四唑吡氨酯(picarbutrazox)、聯苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、寡雄腐霉(Pythium oligandrum)、氟唑菌醯羥胺(pydiflumetofen)、聯苯三唑醇(bitertanol)、樂殺蟎(binapacryl)、檜木醇(hinokitiol)、非病原性細菌性軟腐病菌(Erwinia carotovora)、非病原性葡萄根瘤菌(Rhizobium vitis)、聯苯(biphenyl)、粉病靈(piperalin)、殺紋寧(hymexazol)、唑菌酯(pyraoxystrobin)、百克敏(pyraclostrobin)、必記福敏(pyraziflumid)、白粉松(pyrazophos)、吡普洛潑尼(pyrapropoyne)、唑胺菌酯(pyrametostrobin)、甲氧苯啶菌(pyriofenone)、啶菌唑(pyrisoxazole)、必噠克緹(pyridachlometyl)、啶斑肟(pyrifenox)、稗草丹(pyributicarb)、吡菌苯威(pyribencarb)、嘧黴胺(pyrimethanil)、百快隆(pyroquilon)、免克(vinclozolin)、福美鐵(ferbam)、噁唑菌酮(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)、苯吡克咪徳(fenpicoxamid)、胺苯吡菌酮(fenpyrazamine)、芬克座(fenbuconazole)、甲呋醯苯胺(fenfuram)、苯銹啶(fenpropidin)、芬普福(fenpropimorph)、環醯菌胺(fenhexamid)、福爾培(folpet)、熱必斯(phthalide)、尖孢鐮刀菌(Fusarium oxysporum)、布瑞莫(bupirimate)、麥穗寧(fuberidazole)、保米黴素-S(blasticidin-S)、福拉比(furametpyr)、呋霜靈(furalaxyl)、呋喃羧酸(furancarboxylic acid)、扶吉胺(fluazinam)、氟因菌唑(fluindapyr)、氟啼菌酯(fluoxastrobin)、氟㗁派啉(fluoxapiprolin)、fluoxytioconazole、氟比來(fluopiclide)、氟醚菌醯胺(fluopimomide)、氟吡菌醯胺(fluopyram)、氟醯亞胺(fluoroimide)、氟克殺(fluxapyroxad)、氟喹唑(fluquinconazole)、呋菌唑(furconazole)、呋醚唑(furconazole -cis)、護汰寧(fludioxonil)、護矽得(flusilazole)、氟硫滅(flusulfamide)、噻菌淨(flutianil)、福多寧(flutolanil)、護汰芬(flutriafol)、flufenoxadiazam、氟菌蟎酯(flufenoxystrobin)、氟苯醚醯胺(flubeneteram)、flumetylsulforim、氟醯菌胺(flumetover)、氟嗎啉(flumorph)、大伏革菌(Phlebiopsis gigantea)、普快淨(proquinazid)、撲克拉(prochloraz)、撲滅寧(procymidone)、硫菌威(prothiocarb)、丙硫菌唑(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)、福美昆(flometoquin)、吡啶醯菌胺(florylpicoxamid)、菲克利(hexaconazole)、本達樂(benalaxyl)、本達樂・M(benalaxyl-M)、麥銹靈(benodanil)、免賴得(benomyl)、披扶座(pefurazoate)、平克座(penconazole)、賓克隆(pencycuron)、苯并烯氟菌唑(benzovindiflupyr)、佈生(benthiazole)、苯噻菌胺(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、平氟芬(penflufen)、白克列(boscalid)、福賽得(fosetyl)(包括鋁、鈣、鈉鹽等)、保粒黴素(polyoxin)、代森福美鋅(polycarbamate)、波爾多液(Bordeaux mixture)、代森錳銅(mancopper)、鋅錳乃浦(mancozeb)、曼普胺(mandipropamide)、杏仁菌酯(mandestrobin)、錳乃浦(maneb)、邁克尼(myclobutanil)、礦物油、米多黴素(mildiomycin)、滅速克(methasulfocarb)、威百畝(metam)、滅達樂(metalaxyl)、滅達樂・M(metalaxyl-M)、metarylpicoxamid、免得爛(metiram)、美特洛(metyltetraprole)、滅特座(metconazole)、苯氧菌胺(metominostrobin)、滅芬農(metrafenone)、滅派林(mepanipyrim)、甲分三康唑(mefentrifluconazole)、消蟎多(meptyldinocap)、滅普寧(mepronil)、碘卡佈(iodocarb)、昆布糖(laminarin)、亞磷酸及鹽(phosphorous acid and salts)、鹼性氯化銅(copper oxychloride)、銀(silver)、乙酸銅(copper(II) acetate)、氧化亞銅(cuprous oxide)、氫氧化銅(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-(三級丁基)苯甲酸酯(化學名、CAS註冊編號:1231214-23-5)、BAF-045 (編碼編號)、BAG-010 (編碼編號)、UK-2A(編碼編號)、十二烷基苯磺酸雙乙烯二胺銅錯鹽[II](DBEDC)、MIF-1002 (編碼編號)、NF-180 (編碼編號)、乙酸三苯基錫(TPTA)、三苯基氯化錫(TPTC)、氫氧化三苯基錫(TPTH)及F9650 (編碼編號)。
接著,舉例說明可混合或組合使用的生物殺蟲劑。
生物殺蟲劑:
簡管薊馬(
Haplothrips brevitubus)、細腰兇薊馬(
Franklinothrips vespiformis)、豌豆潛蠅姬小蜂(
Diglyphus isaea)、麗蚜小蜂(
Encarsia formosa)、胡瓜捕植蟎(
Amblyseius cucumeris)、粉蚧玉棒跳小蜂(
Pseudaphycus malinus)、溫氏捕植璊(
Amblyseius womersleyi)、桃赤蚜蚜繭蜂(
Aphidius colemani)、漿角蚜小蜂(
Eretmocerus eremicus)、食蚜癭蚊(
Aphidoletes aphidimyza)、斯氏鈍綏蟎(
Amblyseius swirskii)、南方小花蝽(
Orius strigicollis)、利小植綏蟎(
Phytoseiulus persimilis)、退變鈍綏蟎(
Amblyseius degenerans)、利小植綏蟎(
Phytoseiulus persimilis)、小黑花椿(
Orius sauteri)、反顎繭蜂(
Dacnusa sibirica)、加州捕植蟎(
Amblyseius californicus)、日本通草蛉(
Chrysoperla nipponensis)及紅蠟蚧扁角跳小蜂(
Anicetus beneficus)。
接著,舉例說明可混合或組合使用的農業材料。
農業材料:
乙烯、次氯酸水(限電解於鹽酸或氯化鉀水溶液所得者)、小蘇打、食醋、腐植質、腐植酸、黃腐酸、海藻萃取物、多糖類、胺基酸、微生物材料、源自動植物之機能性成分、微生物代謝物、微生物活性化劑、土壤撒布劑、土壤浸透性調節材料、土壤保水材料等,及生物刺激劑。
接著,舉例說明可混合或組合使用的農業肥料,肥料包括無機肥料與有機肥料。
農業肥料成分:
氯化銨、硫酸銨、硝酸銨、磷酸二氫銨、硝酸尿素銨、尿素、石灰氮、硝酸鉀、過磷酸石灰、重過磷酸石灰、磷酸二氫鉀、氯化鉀、硫酸鉀、碳酸鉀、矽酸鉀、油粕、魚粉、米糠、蝙蝠糞肥、發酵雞糞肥。
如以上所構成的本發明的害蟲防治劑係對於有害生物呈現優異的防治效果,諸如直翅目(Orthoptera)害蟲、纓翅目(Thysanoptera)害蟲、半翅目(Hemiptera)害蟲、鞘翅目(Coleoptera)害蟲、雙翅目(Diptera)害蟲、鱗翅目(Lepidoptera)害蟲、膜翅目(Hymenoptera)害蟲、黏管目(Collembola)害蟲、纓尾目(Thysanura)害蟲、蟑螂害蟲、擬翅目(Psocoptera)害蟲、食毛目(Mallophaga)害蟲、葉翅目(Phthiraptera)害蟲、植物寄生蟎、植物寄生隱桿線蟲(Caenorhabditis)、植物寄生軟體動物(Mollusca)、其他有害動物、令人不快動物、衛生害蟲、寄生蟲等。如此之有害生物,可舉例說明如以下生物種類。
關於直翅目害蟲,可舉例說明如黑頸鉤額蟲(
Ruspolia lineosa)、閻魔蟋蟀(
Teleogryllus emma)、青松蟲(
Truljalia hibinonis)、螻蛄(
Gryllotalpa orientalis)、小翅稻蝗(
Oxya hyla intricate)、殿樣飛蝗(
Locusta migratoria)、遷徙蝗蟲(
Melanoplus sanguinipes)、長額負蝗(
Melanoplus differentialis)、紅腳蝗蟲(
Melanoplus femurrubrum)、負飛蝗(
Atractomorpha lata)、茅蟋蟀(
Euscyrtus japonicus)、日本蚤螻(
Xya japonicus)及其他種類。
關於纓翅目害蟲,可舉例說明如台灣花薊馬(Frankliniella intonsa)、西方花薊馬(
Frankliniella occidentalis)、茶黃薊馬(
Scirtothrips dorsalis)、南黃薊馬(
Thrips palmi)、蔥薊馬(
Thrips tabaci)、大豆淡色薊馬(
Thrips setosus)、變葉木薊馬(
Heliothrips haemorrhoidalis)、稻薊馬(
Stenchaetothrips biformis)等,田薊馬科之柿田薊馬(
Ponticulothrips diospyrosi)、山葵田薊馬(
Liothrips wasabiae)、稻田薊馬(
Haplothrips aculeatus)及其他種類。
關於半翅目害蟲,可舉例說明如姬草蟬(
Mogannia minuta)、白帶尖胸沫蟬(
Aphrophora intermedia)、甘蔗蟲(
Mahanarva fimbriolata)、鳶色角蟬(
Machaerotypus sibiricus)、蓋天姬葉蟬(
Arboridia apicalis)、茶綠姬葉蟬(
Empoasca onukii)、黑尾葉蟬(
Nephotettix cincticeps)、馬來黑尾葉蟬(
Nephotettix malayanus)、台灣黑尾葉蟬(
Nephotettix virescens)、黑條黑尾葉蟬(
Nephotettix nigropictus)、電光葉蟬(
Recilia dorsalis)、小綠葉蟬(
Amrasca biguttula)、檬果褐葉蟬(
Idioscopus nitidulus)、檬果綠葉蟬(
Idioscopus clypealis)、檬果長突葉蟬(
Amritodus atkinsoni)、馬鈴薯姬葉蟬(
Empoasca fabae)、玉米葉蟬(
Dalbulus maidis)、菱飛蝨子(
Pentastiridius apicalis)、班飛蝨(
Laodelphax striatellus)、褐飛蝨(
Nilaparvata lugens)、白背飛蝨(
Sogatella furcifera)、玉蜀黍飛蝨(
Peregrinus maidis)、縞飛蝨(
Nisia nervosa)、白糖斑點飛蝨(
Kamendaka saccharivora)、紅木耳蟲(
Achilus flammeus)、龞甲羽衣(
Orosanga japonicus)、褐綠蛾蠟蟬(
Mimophantia maritima)、梨木蝨(
Cacopsylla pyrisuga)、柑桔木蝨(
Diaphorina citri)、檬果木蝨(
Calophya mangiferae)、葡萄根瘤蚜(
Daktulosphaira vitifoliae)、落葉球蚜蟲(
Adelges laricis)、鐵杉球蚜蟲(
Adelges tsugae)、豌豆長鬚蚜蟲(
Acyrthosiphon pisum)、棉蚜蟲(
Aphis gossypii)、橘捲葉蚜蟲(
Aphis spiraecola)、偽蘿蔔蚜蟲(
Lipaphis erysimi)、蘿蔔蚜蟲(
Brevicoryne brassicae)、桃紅蚜蟲(
Myzus persicae)、麥綠蚜蟲(
Schizaphis graminum)、稻麥蚜蟲(
Rhopalosiphum padi)、小柑桔蚜蟲(
Toxoptera aurautii)、馬鈴薯長鬚蚜蟲(
Aulacorthum solani)、鬱金香長鬚蚜蟲(
Macrosiphum euphorbiae)、萵苣蚜蟲(
Nasonovia ribisnigri)、麥長管蚜蟲(
Sitobion avenae)、大豆蚜蟲(
Aphis glycines)、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)、溫室粉蝨(
Trialeurodes vaporariorum)、草履介殼蟲(
Drosicha corpulenta)、吹棉介殼蟲(
Icerya purchasi)、鳳梨嫡粉介殼蟲(
Dysmicoccus brevipes)、柑桔粉介殼蟲(
Planococcus citri)、桑樹粉介殼蟲(
Pseudococcus comstocki)、角蠟蟲(
Ceroplastes ceriferus)、紅蠟蟲(
Ceroplastes rubens)、甘蔗仁介殼蟲(
Aclerda takahashii)、紅圓介殼蟲(
Aonidiella aurantii)、梨齒盾介殼蟲(
Diaspidiotus perniciosus)、桑擬白介殼蟲(
Pseudaulacaspis pentagoa)、箭頭介殼蟲(
Unaspis yanonensis)、美國牧草盲椿象(
Lygus lineolaris)、赤鬚細綠盲椿象(
Trigonotylus caelestialium)、綠盲椿象(
Apolygus lucorum)、菸草盲椿象(
Nesidiocoris tenuis)、庭園盲椿象(
Halticus bractatus)、杜鵑冠網椿象(
Stephanitis pyrioides)、梨冠網椿象(
Stephanitis nashi)、菜椿象(
Eurydema rugosa)、日本二星椿象(
Eysarcoris lewisi)、北二星椿象(
Eysarcoris aeneus)、稻椿象(
Lagynotomus elongatus)、綠稻椿象(
Nezara viridula)、小珀椿象(
Plautia crossota)、東方稻綠椿象(
Nezara antennata)、自然椿象(
Eushistus heros)、紅帶自然椿象(
Piezodorus guildini)、水稻自然椿象(
Tibraca limbativentris)、綠莓自然椿象(
Dichelops furcatus)、台灣圓椿象(
Mcgacopta cribraria)、梨椿象(
Urochela luteovoria)、甘蔗短翅長椿象(
Cavelerius saccharivorus)、大目高長椿象(
Malcus japonicus)、赤星椿象(
Dysdercus cingulatus)、禾蛛緣椿象(
Leptocorisa acuta)、中稻緣椿象(
Leptocorisa chinensis)、大蛛緣椿象(
Anacanthocoris striicornis)、赤姬緣椿象(
Rhopalus maculatus)、巴式棕色自然椿象(
Scaptocoris castanea)、床蝨(
Cimex lectularis)及其他種類。
關於鞘翅目害蟲,可舉例說明如金銅金龜子(
Anomara cuprea)、姬金龜子(
Anomara rufocuprea)、日本金龜子(Popillia japonica)、小青花金龜子(
Oxycetonia jucunda)、櫻花金龜子(
Anomala geniculata)、犀角金龜子(
Oryctes rhinoceros)、茶色長金龜子(
Heptophylla picea)、六月金龜子(
Phyllophaga cuyabana)、鳶色米象鼻蟲(
Agriotes ogurae)、金針蟲(
Agriotes lineatus)、暗色叩頭蟲(
Agriotes obscurus)、甘蔗鉅天牛(
Melanotus okinawensis)、褐紋金針蟲(
Melanotus fortnumi)、姬圓鰹節蟲(
Anthrenus verbasci)、二突翼翅長心蠹蟲(
Heterobostrychus hamatipennis)、藥材死番蟲(
Stegobium paniceum)、姬蛛甲蟲(
Pitinus clavipes)、穀盜蟲(
Tenebroides mauritanicus)、赤足郭公蟲(
Necrobia rufipes)、醬曲出尾蟲(
Carpophilus hemipterus)、花粉甲蟲(
Meligethes aeneus)、背圓扁粉蟲(
Ahasverus advena)、角胸粉扁蟲(
Cryptolestes ferrugineus)、墨西哥豆甲蟲(
Epilachna varivestis)、茄二十八星瓢蟲(
Henosepilachna vigintioctopunctata)、黃粉蟲(
Tenebrio molitor)、擬穀盜蟲(
Tribolium castaneum)、豆蕪菁(
Epicauta gorhami)、光肩星天牛(
Anoplophora glabripennis)、葡萄虎天牛(
Xylotrechus pyrrhoderus)、松斑天牛(
Monochamus alternatus)、大豆莖螟蟲(
Dectes texanus)、綠豆象蟲(
Callosobruchus chinensis)、科羅拉多金花蟲(
Leptinotarsa decemlineata)、西部玉米食根蟲(
Diabrotica virgifera virgifera)、北部玉米食根蟲(
Diabrotica barberi)、南部玉米食根蟲(
Diabrotica undecimpunctata howardi)、瓜葉蟲(
Aulacophora femoralis)、蘿蔔葉蟲(
Phaedon brassicae)、龜子小葉蟲(
Cassida nebulosa)、負稻泥蟲(
Oulema oryzae)、墨西哥豆甲蟲(
Epilachna varivestis)、黃條葉蚤(
Phyllotreta striolata)、茶肖葉甲蟲(
Demotina fasciculata)、捲心菜跳蚤甲蟲(
Psylliodes chrysocephala)、大豆葉甲蟲(
Cerotoma trifurcate)、葡萄削葉甲蟲(
Colaspis brunnea)、艾俄華削葉甲蟲(
Colaspis crinnicornis)、豆潛葉蟲(
Odontota horni)、甜菜跳甲蟲(
Chaetocnema pulicaria)、帶斑黃瓜葉甲蟲(
Diabrotica balteata)、甘藷蟻象蟲(
Cylas formicarius)、苜蓿象鼻蟲(
Hypera postica)、蔬菜象鼻蟲(
Listroderes costirostris)、甘藷象鼻蟲(
Euscepes postfasciatus)、栗果象鼻蟲(
Curculio sikkimensis)、苜蓿葉象鼻蟲(
Anthonomus grandis)、大豆莖象鼻蟲(
Sternechus subsignatus)、稻象鼻蟲(
Echinocnemus bipunctatus)、稻水象鼻蟲(
Lissorhoptrus oryzophilus)、南美稻米水象鼻蟲(
Oryzophagus oryzae)、玉米象鼻蟲(
Sitophilus zeamais)、狩獵長喙象鼻蟲(
Sphenophrus venatus)、甘蔗象鼻蟲(
Sphenophorus levis)、松木蠹蟲(
Tomicus piniperda)、台日截尾長小蠹蟲(
Crossotarsus niponicus)、褐粉蠹蟲(
Lyctus brunneus)及其他種類。
關於雙翅目害蟲,可舉例說明如大蚊科之稻大蚊(
Tipula aino)、愛蟲(
Plecia nearctica)、蕈蚋(
Exechia shiitakevora)、馬鈴薯黑翅蕈蚊(
Pnyxia scabiei)、小黑翅蕈蚊(
Bradysia agrestis)、大豆莢癭蚊(
Asphondylia yushimai)、黑森癭蚊(
Mayetiola destructor)、黑莓癭蚊(
Dasineura oxycoccana)、埃及伊蚊(Aedes aegypti)、淡色庫蚊(
Culex pipiens pallens)、素木蚋(
Simulium takahashii)、稻搖蚊(
Chironomus oryzae)、合瘤斑蚊(
Chrysops suavis)、牛虻(
Tabanus trigonus)、洋蔥平顏蚜蠅(
Eumerus strigatus)、柑桔小果蠅(
Bactrocera dorsalis)、日本櫻桃果蠅(
Euphranta japonica)、地中海果蠅(
Ceratitis capitata)、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)、豌豆葉潛蠅(
Chromatomyia horticola)、中華蔥斑潛蠅(
Liriomyza chinensis)、黑腹麥稈潛蠅(
Meromyza nigriventris)、斑翅果蠅(
Drosophila suzukii)、黃果蠅(
Drosophila melanogaster)、大麥水蠅(
Hydrellia griseola)、馬風蠅(
Hippobosca equina)、謝意笹川糞蠅(
Parallelpmma sasakawae)等,花蠅科之洋蔥蠅(
Delia antiqua)、歐洲花蠅(
Delia platura)、夏廁蠅(
Fannia canicularis)、家蠅(
Musca domestica)、整蠅(
Stomoxys calcitrans)、遊蕩肉蠅(
Sarcophaga peregrina)、馬蠅(
Gasterophilus intestinalis)、牛蠅(
Hypoderma lineatum)、綿羊鼻蠅(
Oestrus ovis)及其他種類。
關於鱗翅目害蟲,可舉例說明如淡緣幅蛾(
Endoclita excrescens)、葡萄果蠹蛾(
Antispila ampelopsia)、六星黑點豹蠹蛾(
Zeuzera leuconotum)、姬木蠹蛾(
Cossus insularis)、亂蚊蘋果捲葉蠅(
Archips fuscocupreanus)、蘋果小褐斑捲葉蛾(
Adoxophyes orana fasciata)、小食心蟲(
Grapholita molesta)、茶捲葉蛾(
Homona magnanima)、大豆食心蟲(
Leguminivora glycinivorella)、蘋果蠹蛾(
Cydia pomonella)、歐洲葡萄藤蛾(
Lobesia botrana)、葡萄與蘋果捲葉蛾(
Eupoecilia ambiguella)、黑艷蓑蛾(
Bambalina sp.)、茶蓑蛾(
Eumeta minuscula)、歐谷蛾(
Nemapogon granella)、衣蛾(
Tinea translucens)、梨菱巢蛾(
Bucculatrix pyrivorella)、桃潛葉蛾(
Lyonetia clerkella)、銀紋潛葉蛾(
Lyonetia prunifoliella malinella)、茶細蛾(
Caloptilia theivora)、銀紋細蛾(
Phyllonorycter ringoniella)、柑桔小潛葉蛾(
Phyllocnistis citrella)、蔥菜蛾(
Acrolepiopsis sapporensis)、小菜蛾(
Plutella xylostella)、蘋果巢蛾(
Yponomeuta orientalis)、蘋果小食心蛾(
Argyresthia conjugella)、葡萄透翅蛾(
Nokona regalis)、小透翅蛾(
Synanthedin hector)、馬鈴薯塊莖蛾(
Phthorimaea operculella)、麥蛾(
Sitotroga cerealella)、棉紅鈴蟲(
Pectinophora gossypiella)、番茄潛旋蛾(
Tuta absoluta)、桃食心蛾(
Carposina sasakii)、梨星毛蟲(
Illiberis pruni)、黃刺蛾(
Monema flavescens)、稻巢草螟蛾(
Ancylolomia japonica)、二化螟蛾(
Chilo suppressalis)、瘤野螟蛾(
Cnaphalocrocis medinalis)、亞洲玉米螟蛾(
Ostrinia furnacalis)、菜心螟蛾(
Hellulla undalis)、桃蛀野螟蛾(
Conogethes punctiferlis)、瓜絹野螟蛾(
Diaphania indica)、禾擬莖草螟蛾(
Parapediasia teterrella)、歐洲玉米螟蟲(
Ostrinia nubilalis)、甘蔗螟蟲(
Diatraea saccharalis)、粉斑螟蛾(
Cadra cautella)、大蠟螟蛾(
Galleria mellonella)、葡萄羽蛾(
Nippoptilia vitis)、柑橘鳳蝶(
Papilio xuthus)、菜粉蝶(
Pieris rapae)、稻弄蝶(
Parnara guttata)、腎斑尺蛾(
Ascotis selenaria)、赤松毛蟲(
Dendrolimus spectabilis)、帶枯葉蛾(
Malacosoma neustrium testaceum)、蝦殼天蛾(
Agrius convolvuli)、茶毒蛾(
Arna pseudoconspersa)、姬白紋毒蛾(
Orygia recens approximans)、舞毒蛾(
Lymantria dispar)、美國白蛾(
Hyphantria cunea)、小地老虎蛾(
Agrotis ipsilon)、黃地老虎蛾(
Agrotis segetum)、豆銀紋夜蛾(
Autographa nigrisigna)、棉鈴實夜蛾(
Helicoverpa armigera)、玉米穗蟲(
Helicoverpa zea)、烟蚜夜蟲(
Heliothis virescens)、甜菜葉蛾(
Spodoptera exigua)、斜紋葉盜蛾(
Spodoptera litura)、黃豆尺夜蛾(
Chrysodeixis includens)、草地貪夜蛾(
Spodoptera frugiperda)、銅色切夜蛾(
Nephelodes minians)及其他種類。
關於膜翅目害蟲,可舉例說明如玫瑰三節葉蜂(
Arge pagana)、栗葉蜂(
Apethymus kuri)、紅角菜葉蜂(
Athalia rosae ruficornis)、板栗癭蜂(
Dryocosmus kuriphilus)、黃胡蜂(
Vespa simillima xanthoptera)、入侵紅火蟻(
Solenopsis invicta)、阿根廷蟻(
Linepithema humile)、薔薇切葉蜂(
Megachile nipponica)及其他種類。
關於黏管目害蟲,可舉例說明如黃星圓跳蚤(
Bourletiella hortensis)及其他種類。
關於纓尾目害蟲,可舉例說明如西洋蠹魚(
Lepisma saccharina)、敏櫛蠹魚(
Ctenolepisma villosa)及其他種類。
關於蟑螂害蟲,可舉例說明如美洲蜚蠊(
Periplaneta americana)、德國蜚蠊(
Blattella germanica)、台灣白蟻(
Odontotermes formosanus)、美國乾材白蟻(
Incisitermes minor)、截頭堆砂白蟻(
Cryptotermes domesticus)、家白蟻(
Coptotermes formosanus)、日本白蟻(
Reticulitermes speratus)及其他種類。
關於擬翅目害蟲,可舉例說明如粉茶蛀蟲(
Trogium pulsatorium)
、書蠹(
Liposcelis corrodens)及其他種類。
關於革翅目害蟲,可舉例說明如蠼螋(
Labodura riparia)及其他種類。
關於食毛目害蟲,可舉例說明如火雞翅長圓蝨(
Lipeurus caponis)、牛蝨(
Damalinia bovis)及其他種類。
關於葉翅目害蟲,可舉例說明如豬蝨(
Haematopinus suis)、人蝨(
Pediculus humanus)、狗蝨(
Linognathus setosus)、陰蝨(
Pthirus pubis)及其他種類。
關於蟎害蟲,可舉例說明如麥圓紅蜘蛛(
Penthaleus major)、櫻草植食蟎(
Phytonemus pallidus)、茶細蟎(Polyphagotarsonemus latus)、蒲蟎(
Siteroptes sp.)、葡萄短須蟎(
Brevipalpus lewisi)、孔雀杜克葉蟎(
Tuckerella pavoniformis)、北始葉蟎(
Eotetranychus boreus)、柑桔葉蟎(
Panonychus citri)、蘋果葉蟎(
Panonychus ulmi)、二斑葉蟎(
Tetranychus urticae)、神澤氏葉蟎(
Tetranychus kanzawai)、松節蟎(
Trisetacus pini)、柑桔皮節蜱(
Aculops pelekassi)、梨銹蜱(
Epitrimerus pyri)、柑桔銹蟎(
Phyllocoptruta oleivora)、番茄銹蟎(
Aculops lycopersici)、冬青節蟎(
Diptacus crenatae)、橢圓斑白蟎(
Aleuroglyphus ovatus)、腐蝕酪蟎(
Tyrophagus putrescentiae)、羅賓根蟎(
Rhizoglyphus robini)、蜜蜂蟹蟎(
Varroa jaeobsoni)、雞皮刺蟎(
Dermanyssus gallinae)、禽刺蟎(
Ornithonyssus sylviarum)、微小牛蟎(
Boophilus microplus)、血紅扇頭蟎(
Rhipicephalussanguineus)、長角血蟎(
Haemaphysalis longicornis)、疥蟎(
Sarcoptes scabiei)及其他種類。
關於植物寄生隱桿線蟲,可舉例說明如劍線蟲(
Xiphinema index)、較小擬毛刺線蟲(
Paratrichodorus minor)、同桿線蟲屬(
Rhabditella sp.)、野外墊刃屬(
Aglenchussp.)、頭刀線蟲屬(
Cephalenchus sp.)、草莓芽線蟲(
Nothotylenchus acris)、腐爛莖線蟲(
Ditylenchus destructor)、腎形線蟲(
Rotylenchulus reniformis)、雙宮螺旋線蟲(
Helicotylenchus dihystera)、針線蟲(
Paratylenchus curvitatus)、南方根瘤線蟲(
Meloidogyne incognita)、北方根瘤線蟲(
Meloidogyne hapla)、爪哇根瘤線蟲(
Meloidogyne javanjca)、哥倫比亞根瘤線蟲(
Meloidogyne chitwoodi)、偽哥倫比亞根瘤線蟲(
Meloidogyne fallax)、黃金線蟲(
Globodera rostochiensis)、馬鈴薯金線蟲(
Globodera pallida)、大豆萎黃線蟲(
Heterodera glycines)、甜菜囊腫線蟲(
Heterodera Schachtii)、矮化線蟲(
Tylenchorhynchus claytoni)、螺旋線蟲屬(
Psilenchus sp.)、環紋線蟲屬(
Criconemoides sp.)、柑桔線蟲(
Tylenchulus semipenetrans)、山茶花丸線蟲(
Sphaeronema camelliae)、柑桔穿孔線蟲(
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)、咖啡根腐線蟲(
Pratylenchus coffeae)、摩洛哥根腐線蟲(
Pratylenchus zeae)、鳳梨根腐線蟲(
Pratylenchus brachyurus)、平菇根瘤線蟲(
Iotonchium ungulatum)、燕麥真滑刃線蟲(
Aphelenchus avenae)、貝西滑刃線蟲(
Aphelenchoides besseyi)、草莓線蟲(
Aphelenchoides fragariae)、松材線蟲(
Bursaphelenchus xylophilus)及其他種類。
關於植物寄生軟體動物,可舉例說明如福壽螺(
Pomacea canaliculata)、皺足蛞蝓(
Leavicaulis alte)、非洲大蝸牛(
Achatina fulica)、雙線蛞蝓(
Meghimatium bilineatum)、琥珀蝸牛(
Succinea lauta)、淺圓盤羅(
Discus pauper)、琥珀蝸牛(
Zonitoides yessoensis)、黃蛞蝓(
Limax flavus)、亞列蛞蝓(
Lehmannia valentiana)、網紋野蛞蝓(
Deroceras reticulatum)、黍蝸牛(
Parakaliella harimensis)、琉球球蝸牛(
Acusta despecta sieboldiana)、扁蝸牛(
Bradybaena similaris)及其他種類。
關於其他有害生物,諸如有害動物、令人不快動物、衛生害蟲、家畜害蟲、寄生蟲等,可舉例說明如美國螯蝦(
Procambarus clarkii)
、草鞋蟲(
Porcellio scaber)、鼠腹(
Armadillidium vulgare)、千足 (Chilopoda)害蟲,諸如花蚰蜓(
Thereuonema tuberculata)及蜈蚣(
Scolopendra subspinipes)
、雙足類(Diplopoda)害蟲,諸如溫室馬陸(
Oxidus gracilis)
、赤背寡婦蜘蛛(
Theridiidae hasseltii)
、日本紅螯蜘蛛(
Cheiracanthium japouicum)
、黑肥尾蠍(
Androctonus crassicauda)
、線形動物內部寄生蟲, 諸如人蛔蟲(
Ascaris lumbricoides)、蟯蟲屬(
Syphaciasp.)及潘氏絲狀蟲(
Wuchereria bancrofti)、扁蟲之內部寄生蟲,諸如雙盤吸蟲屬(
Distomumsp.)、肺吸蟲(
Paragonimus westermanii)
、横川吸蟲(
Metagonimus yokokawai)、日本住血吸蟲(
Schistosoma japonicum)
、有鉤條蟲(
Taenia solium)、無鉤條蟲(
Taeniarhynchus saginatus)、包囊蟲(
Echinococcussp.)、廣節裂頭條蟲(
Diphyllobothrium latum) 及其他種類。
本發明的害蟲防治劑對於現存害蟲防治劑已獲得抗性的上述列舉的害蟲等亦呈現防治效果。此外,本發明的害蟲防治劑亦可用於藉由基因重組、人工交配等獲得抗害蟲、抗病、抗除草劑等特性的植物。
本發明之「藉由育種法或基因重組技術賦予耐性之植物」不僅包含以標準品種育種及基因重組技術賦予耐性,亦包含那些藉由將分子生物學技術與傳統育種技術相結合的新植物育種技術(NBT)產生抗性的植物。新植物育種技術(NBT) 記載於書籍「Let's Understand New Plant Breeding Technology」(International Literature Company,Ryo Osawa and Hiroshi Egami),評論記事「Genome Editing Tools in Plants」(Genes 2017, 8, 399, Tapan Kumar Mohanta, Tufail Bashir, Abeer Hashem, Elsayed Fathi Abd_Allah, and Hanhong Bae)等。
實施例其次,以下述之實施例詳細說明本發明化合物之製造方法、調配物方法及其用途。然而,本發明不受此等實施例限制。關於本發明化合物之物理性質,熔點以Yanaco MP-500 V微熔點儀測量,使用Atago製造之Abbe折射儀測量折射率,且以藉由使用四甲基矽烷(TMS)作為內標的JEOL所製造的JNM-ECS300 (300 MHz)量測
1H-NMR光譜。
此外,亦敘述用於製造本發明化合物之中間體的方法。
實例1
製造1-[3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(本發明化合物編號:A-0479)
1) 2-[4-(芐氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶
將根據國際公開號2019/124548合成之2-溴-6-(三氟甲基)咪唑并[1,2-a]吡啶(1.0 g, 3.8 mmol、4-(芐氧基)-1H-吡唑 (0.66 g, 3.8 mmol)、碘化亞銅(I) (0.36 g, 1.9 mmol)、N,N'-二甲基伸乙基二胺 (0.17 g, 1.9 mmol)及磷酸三鉀正水合物(1.6 g, 7.5 mmol as anhydrate)依序添加至N-甲基-2-吡咯啶酮(7.5 mL),並在密封管中於140℃進一步攪拌8小時。將反應溶液倒入稀釋氨水中。添加乙酸乙酯,並將混合物通過矽藻土過濾。有機層以水和飽和鹽水洗滌。有機層經過無水硫酸鎂乾燥,並在減壓下蒸餾除去溶劑。殘餘物藉由矽膠管柱層析純化,並獲得2-[4- (芐氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶(0.40 g,產率:30%)。
1H-NMR數據(300 MHz,CDCl
3/TMS δ (ppm)): 5.03 (2H, s), 7.31-7.46 (6H, m), 7.53 (1H, s), 7.64 (1H, d), 7.88 (1H, s), 8.02 (1H, s), 8.49 (1H, br s)
2) 2-[4-(芐氧基)-1H-吡唑-1-基]-3-碘-6-(三氟甲基)咪唑并[1,2-a]吡啶
將2-[4-(芐氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶 (0.40 g, 1.1 mmol)溶於乙腈(11 mL)。將N-碘琥珀醯亞胺(0.30 g,1.3 mmol)加入混合物,並在室溫下進一步攪拌隔夜。將反應溶液倒入硫代硫酸鈉水溶液中並用乙酸乙酯萃取。有機層依次以碳酸鉀水溶液和硫代硫酸鈉水溶液洗滌,並將有機層經由無水硫酸鎂乾燥。在減壓下蒸餾除去溶劑,並獲得2-[4-(芐氧基)-1H-吡唑-1-基]-3-碘-6-(三氟甲基)咪唑并[1,2-a]吡啶(0.46 g,產率:85%)。
1H-NMR數據(300 MHz, CDCl
3/ TMS δ (ppm)): 5.04 (2H, s), 7.32-7.48 (6H, m), 7.63 (1H, d), 7.64 (1H, d), 8.03 (1H, d), 8.62-8.63 (1H, m)
3) 製造1-[3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(本發明化合物編號:A-0479)
將2-[4-(芐氧基)-1H-吡唑-1-基]-3-碘-6-(三氟甲基)咪唑并[1,2-a]吡啶(0.46 g, 0.95 mmol)、乙硫醇(0.69 mL, 9.6 mmol)、N,N-二異丙基乙基胺(0.15 g, 1.2 mmol)、三(二亞芐基丙酮)二鈀(0) (0.043 g, 0.047 mmol)及Xantphos (0.055 g, 0.095 mmol)依序添加至1,4-二㗁烷(9.5 mL),並將混合物在加熱回流下進一步攪拌3小時。濃縮反應溶液。殘餘物藉由矽膠管柱層析純化,並獲得2-[4-(芐氧基)-1H-吡唑-1-基]-3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶。將所獲得之2-[4-(芐氧基)-1H-吡唑-1-基]-3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶溶於硝基甲烷(9.5 mL)。將氯化鋁(0.29 g,2.2 mmol)加入混合物,並在室溫下進一步攪1小時。將反應溶液倒入稀鹽酸並以乙酸乙酯萃取。有機層經過無水硫酸鎂乾燥,並在減壓下蒸餾除去溶劑。將殘餘物以己烷/二異丙基醚(1:1)混合溶液洗滌,並獲得1-[3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-ol (0.27 g,產率:86%)。
1H-NMR數據(300 MHz, DMSO-d
6/ TMS δ (ppm)): 1.06 (3H, t), 2.91 (2H, q), 7.52 (1H, d), 7.71 (1H, dd), 7.85 (1H, d), 7.90 ( 1H, d), 8.97 (1H, br s), 9.08 (1H, s)
熔點:199-202°C
實例2
製造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-(三氟甲基)咪唑并[1,2-a]吡啶(本發明化合物編號:A-0046)
將1-[3-(乙基硫基)-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(0.27 g, 0.82 mmol)、碳酸鉀(0.17 g, 1.2 mmol)及2,2,3,3,4,4,4-七氟丁基九氟丁磺酸酯(0.44 g, 0.91 mmol)依序添加至N,N-二甲基甲醯胺(8.2 mL),並將混合物在室溫進一步攪拌隔夜。將反應溶液倒入水中並以乙酸乙酯萃取。有機層以水和飽和鹽水洗滌,並將有機層經由無水硫酸鎂乾燥。在減壓下蒸餾去除溶劑,並獲得3-(乙基硫基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶。將所獲得之3-(乙基硫基)-2-[4-(2,2,3,3,4,4,4-七氟丁氧基)-1H-吡唑-1-基]-6-(三氟甲基)咪唑并[1,2-a]吡啶溶於二氯甲烷(7.3 mL)。將M-氯過苯甲酸(含量:77%, 0.35 g,1.6 mmol)加入混合物,並在室溫下進一步攪3小時。將反應溶液倒入碳酸鉀水溶液中並用乙酸乙酯萃取。有機層經過無水硫酸鎂乾燥,並在減壓下蒸餾除去溶劑。殘餘物藉由矽膠管柱層析純化,並獲得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-(三氟甲基)咪唑并[1,2-a]吡啶(0.26 g, 產率:66%)。
1H-NMR數據(300 MHz, CDCl
3/ TMS δ (ppm)): 1.42 (3H, t), 3.91 (2H, q), 4.44 (2H, tt),7.66 (1H, dd), 7.67 (1H, d), 7.77 (1H, d), 8.06 (1H, d), 9.63-9.65 (1H, m)
熔點:134-136°C
實例3
製造2-[4-(芐氧基)-1H-吡唑-1-基]-6-溴-3-(乙基磺醯基)咪唑并[1,2-a]吡啶(本發明化合物編號:A-0612)
1) 6-溴-2-氯-3-(乙基硫基)咪唑并[1,2-a] 吡啶
將根據國際公開號2009/144395說明書之敘述所合成之6-溴-2-氯咪唑并[1,2-a] 吡啶 (3.50 g, 15 mmol)、二乙基二硫醚(2.77 g, 23 mmol)及碘苯二乙酸酯(7.31 g, 23 mmol)依序添加至乙腈(30 mL),並將混合物在加熱下進一步攪拌,並回流4小時。將反應溶液倒入硫代硫酸鈉水溶液中並用乙酸乙酯萃取。有機層以水和飽和鹽水洗滌。有機層經過無水硫酸鎂乾燥,並在減壓下蒸餾除去溶劑。殘餘物藉由矽膠管柱層析純化。獲得6-溴-2-氯-3-(乙基硫基)咪唑并[1,2-a]吡啶(3.81 g, 產率:86%)。
1H-NMR數據(300 MHz, CDCl
3/ TMS δ (ppm)): 1.23 (3H, t), 2.75 (2H, q), 7.37 (1H, dd), 7.47 (1H, dd), 8.51 (1H, d)
2) 6-溴-2-氯-3-(乙基磺醯基)咪唑并[1,2-a]吡啶
將6-溴-2-氯-3-(乙基硫基)咪唑并[1,2-a] 吡啶 (3.81 g, 13 mmol)溶於氯仿(65 mL)。在冰冷卻下將M-氯過苯甲酸(含量:70%,8.05 g,33 mmol)添加至混合物中,並進一步在室溫攪拌3小時。將反應溶液倒入碳酸鉀水溶液中。加入硫代硫酸鈉水溶液,並以氯仿萃取。有機層以碳酸鉀水溶液和飽和鹽水洗滌,並經由無水硫酸鎂乾燥。在減壓下餾除溶劑。獲得6-溴-2-氯-3-(乙基磺醯基)咪唑并[1,2-a]吡啶(4.20 g, 產率:99%)。
1H-NMR數據(300 MHz, CDCl
3/ TMS δ (ppm)): 1.36 (3H, t), 3.37 (2H, q), 7.58 (2H, m), 9.16 (1H, d)
3) 2-[4-(芐氧基)-1H-吡唑-1-基]-6-溴-3-(乙基磺醯基) 咪唑并[1,2-a] 吡啶 (本發明化合物編號:A-0612)
將6-溴-2-氯-3-(乙基磺醯基)咪唑并[1,2-a]吡啶(4.13 g, 13 mmol)、4-(芐氧基)-1H-吡唑(2.45 g, 14 mmol)及碳酸銫(6.24 g, 19 mmol)依序添加至二甲亞碸 (26 mL),並在100°C進一步攪拌8小時。將反應溶液倒入水中並以乙酸乙酯萃取。有機層以飽和鹽水洗滌,經由無水硫酸鎂乾燥,並在減壓下蒸餾除去溶劑。殘餘物以丙酮/二異丙醚(1:1)的混合溶劑洗滌。獲得2-[4-(芐氧基)-1H-吡唑-1-基]-6-溴-3-(乙基磺醯基)咪唑并[1,2-a]吡啶(2.68 g,產率:46%)。
1H-NMR數據(300 MHz, DMSO-d
6/ TMS δ (ppm)): 1.30 (3H, t), 3.90 (2H, q), 5.09 (2H, s), 7.32-7.49 (5H, m), 7.78-7.87 (3H, m), 8.16 (1H, d), 9.17 (1H, d)
實例4
製造1-[6-溴-3-(乙基磺醯基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(本發明化合物編號:A-0476)
將2-[4-(芐氧基)-1H-吡唑-1-基]-6-溴-3-(乙基磺醯基)咪唑并[1,2-a]吡啶(2.68 g, 5.8 mmol)溶於硝基甲烷(29 mL)及二氯甲烷(29 mL)中。將氯化鋁(1.55 g, 12 mmol)添加至混合物中,並在室溫進一步攪拌1小時。將稀鹽酸倒入反應溶液中,並加入二異丙醚以沉澱粗晶體。以二異丙醚洗滌粗晶體。獲得1-[6-溴-3-(乙基磺醯基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(1.72 g,產率:80%)。
1H-NMR數據(300 MHz, DMSO-d
6/ TMS δ (ppm)): 1.29 (3H, t), 3.90 (2H, q), 7.54 (1H, d), 7.77-7.85 (3H, m), 9.17 (1H, d), 9 .17 (1H, br s)
實例5
製造6-溴-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]咪唑并[1,2-a]吡啶(本發明化合物編號:A-0039)
將1-[6-溴-3-(乙基磺醯基)咪唑并[1,2-a]吡啶-2-基]-1H-吡唑-4-醇(1.58 g, 4.3 mmol)、碳酸鉀(0.88 g, 6.4 mmol)及2,2,3,3,4,4,4-七氟丁基 九氟丁磺酸酯(2.26 g, 4.7 mmol)依序添加至乙腈(21 mL),並進一步於80°C攪拌4小時。濃縮反應溶液,並將殘餘物藉由矽膠管柱層析純化。6-溴-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]咪唑并[1,2-a]吡啶(2.13 g,產率:90%)。
1H-NMR數據(300 MHz, CDCl
3/ TMS δ (ppm)): 1.40 (3H, t), 3.87 (2H, q), 4.43 (2H, tt), 7.53-7.65 (3H, m), 8.01 (1H, d), 9.38 (1H, d)
熔點:171-174°C
實例6
製造6-環丙基-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]咪唑并[1,2-a]吡啶(本發明化合物編號:A-0049)
將6-溴-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]咪唑并[1,2-a]吡啶(4.25 g, 7.7 mmol)、環丙基硼酸(1.32 g, 15 mmol)、磷酸三鉀正水合物(4.89 g, 23 mmol作為無水物)、乙酸鈀(II) (0.086 g, 0.38 mmol)及2-二環己基膦-2',6'-二甲氧基聯苯基(0.32 g, 0.78 mmol)依序加入1,4-二㗁烷(40 mL)及水(4 mL)中,並在加熱下進一步攪拌並回流6小時。將反應溶液倒入水中並以乙酸乙酯萃取。有機層以水及飽和鹽水洗滌,經過無水硫酸鎂乾燥,並在減壓下蒸餾除去溶劑。殘餘物藉由矽膠管柱層析純化。獲得6-環丙基-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]咪唑并[1,2-a]吡啶(2.02 g,產率:52%)。
1H-NMR數據(300 MHz, CDCl
3/ TMS δ (ppm)): 0.76 (2H, m), 1.06 (2H, m), 1.39 (3H, t), 1.99 (1H, m), 3.81 (2H, q), 4.42 (2H, tt), 7.21 (1H, dd), 7.55 (1H, dd), 7.62 (1H, d), 7.98 (1H, d), 9.01 (1H, d)
熔點:117-120°C
根據上述實施例合成的本發明化合物[I]的物理性質值顯示於下表25至30中,包括上述實施例中的值。表中的化合物編號和符號具有如上述相同的含義。
其次,將具體描述使用如上述製造的雜環化合物或其農業上可接受的鹽的本發明害蟲防治劑的調配物實施例。然而,化合物和添加劑的類型和混合比例並不限於此,並可在很寬的範圍內變化。此外,在以下說明中,「份」是指質量份。
[調配物實施例1] 乳劑
表1至24中所列之化合物 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
將上述成分均勻溶解以獲得乳劑。
[調配物實施例2] 可濕性粉劑
表1至24中所列之化合物 10 份
萘磺酸福馬林冷凝液鈉鹽 0.5 份
聚氧乙烯烷基芳基醚 0.5 份
矽藻土 24 份
黏土 65 份
將上述成分混合均勻並粉碎以獲得可濕性粉劑。
[調配物實施例3] 粉劑
表1至24中所列之化合物 2 份
矽藻土 5 份
黏土 93 份
將上述成分混合均勻並粉碎以獲得粉劑。
[調配物實施例4] 顆粒
表1至24中所列之化合物 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
將上述成分混合均勻並粉碎。將相當於20份之數量的水加入混合物中,捏合,使用擠壓造粒機加工成14至32網目之顆粒,然後乾燥以獲得顆粒。
[調配物實施例5] 懸浮濃縮物
表1至24中所列之化合物 20 份
聚氧乙烯苯乙烯化苯醚硫酸鹽 4 份
乙二醇 7 份
聚矽氧AF-118N (Asahi Kasei製) 0.02 份
水 68.98 份
將上述成分以高速攪拌器混合30分鐘,然後以濕式粉碎機粉碎以獲得懸浮濃縮物。
[調配物實施例6] 水分散性顆粒
表1至24中所列之化合物 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
預糊化澱粉 1 份
碳酸鈣 65 份
水 10 份
將上述成分混合、捏合、壓制和造粒。將獲得的顆粒在流體化床乾燥器中乾燥以獲得水分散性顆粒。
接著,參照測試實施例說明本發明的害蟲防治劑的效果。
[測試實施例1] 對於小菜蛾(
Plutella xylostella)之殺蟲活性測試
將根據調配物實施例2製備之可濕性粉劑以水稀釋至500 ppm之濃度來作為活性成分。將一些高麗菜葉浸入藥物溶液中,風乾,然後放入塑料杯中。將10隻小菜蛾二齡幼蟲放在處理過的葉子上,並蓋上蓋子。然後,將其放置在恆溫25°C的房間中。在處理後6天調查死亡昆蟲的數量。使用式1計算死亡率。在每個測試中重複的數量是一次。
以下列出在測試中顯示出 90%或更高死亡率的化合物編號。
A-0003、A-0005、A-0006、A-0038、A-0039、A-0042、A-0044、A-0045、A-0046、A-0047、A-0049、A-0050、A-0056、A-0058、A-0060、A-0068、A-0075、A-0162、A-0164、A-0183、A-0184、A-0185、A-0189、A-0191、A-0192、A-0193、A-0195、A-0199、A-0207、A-0209、A-0210、A-0213、A-0218、A-0256、A-0259、A-0274、A-0423、A-0426、A-0458、A-0579、A-0580、A-0581、A-0582、A-0583、A-0584、A-0585、A-0587、A-0589、A-0590、A-0591、A-0592、A-0593、A-0594、A-0595、A-0596、A-0597、A-0598、A-0599、A-0600、A-0602、A-0603、A-0604、A-0605、A-0606、A-0607、A-0608、A-0610、A-0611、A-0613、A-0614、A-0615、B-0002、C-0030、D-0006、D-0021。
[測試實施例2] 對於棉鈴實夜蛾(
Helicoverpa armigera)之殺蟲活性測試
將根據調配物實施例2製備之可濕性粉劑以水稀釋至500 ppm之濃度來作為活性成分。將一些高麗菜葉浸入藥物溶液中,風乾,然後放入塑料杯中。將5隻棉鈴實夜蛾孵化幼蟲放在處理過的葉子上,並蓋上蓋子。然後,將其放置在恆溫25°C的房間中。在處理後6天調查死亡昆蟲的數量。使用式1計算死亡率。在每個測試中重複的數量是二次。
以下列出在測試中顯示出 90%或更高死亡率的化合物編號。
A-0003、A-0005、A-0006、A-0038、A-0039、A-0044、A-0046、A-0049、A-0058、A-0183、A-0207、A-0209、A-0210、A-0213、A-0218、A-0259、A-0274、A-0423、A-0426、A-0458、A-0583、A-0584、A-0587、A-0589、A-0591、D-0006、D-0021。
[測試實施例3] 對於褐飛蝨(
Nilaparvata lugens)之殺蟲活性測試
將根據調配物實施例2製備之可濕性粉劑以水稀釋至500 ppm之濃度來作為活性成分。將一些稻米芽浸入藥物溶液中並放入塑料杯中。將10隻褐飛蝨二齡幼蟲放在處理過的葉子上,並蓋上蓋子。然後,將其置於25°C的恆定室溫中。在處理後6天調查死亡昆蟲的數量。使用式1計算死亡率。在每個測試中重複的數量是一次。
以下列出在測試中顯示出 90%或更高死亡率的化合物編號。
A-0003、A-0005、A-0006、A-0038、A-0039、A-0044、A-0045、A-0046、A-0049、A-0050、A-0056、A-0058、A-0162、A-0164、A-0183、A-0184、A-0210、A-0213、A-0218、A-0579、A-0580、A-0584、A-0592、A-0593、A-0594、A-0595、A-0600、A-0605、A-0611、A-0613、A-0614、C-0026。
[測試實施例 4]對於棉蚜蟲(
Aphis gossypii) 之害蟲防治效果測試
將根據調配物實施例2製備之可濕性粉劑以水稀釋至500 ppm之濃度來作為活性成分。將一些先前接種有棉蚜幼蟲的黃瓜苗圃浸入藥物溶液中並風乾。將處理過的黃瓜苗圃置於25℃恆溫的室內。在處理後3天計數存活昆蟲的數量。使用式1計算死亡率。在每個測試中重複的數量是一次。
[0356]
以下列出在測試中顯示出 90%或更高死亡率的化合物編號。
A-0003、A-0005、A-0006、A-0038、A-0039、A-0042、A-0044、A-0045、A-0046、A-0047、A-0049、A-0050、A-0056、A-0058、A-0162、A-0164、A-0183、A-0184、A-0185、A-0189、A-0191、A-0195、A-0199、A-0207、A-0210、A-0213、A-0218、A-0259、A-0274、A-0423、A-0426、A-0579、A-0580、A-0581、A-0582、A-0584、A-0585、A-0589、A-0590、A-0591、A-0592、A-0593、A-0594、A-0595、A-0596、A-0597、A-0598、A-0599、A-0600、A-0603、A-0604、A-0605、A-0607、A-0608、A-0610、A-0611、A-0614、C-0026、D-0006、D-0021。
產業可利用性本發明提供具有優異殺蟲活性的新穎化合物、其生產中間體以及含有該化合物作為活性成分的害蟲防治劑。其可用於農藥和農業領域,並具有工業用途的潛力。
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Claims (26)
- 一種通式[I]表示之化合物或其鹽,其中, m及n各獨立地代表0、1或2之整數,且其總合為0至2之整數, R 1代表氫原子、氰基或未經取代或經鹵原子取代之C 1-C 7醯基, R 2代表C 1-C 6烷基、C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6鹵烷基、C 1-C 6烷氧基C 1-C 6鹵烷基、C 1-C 6鹵烷氧基C 1-C 6烷基、C 1-C 6鹵烷氧基C 1-C 6鹵烷基、C 3-C 6環烷基、C 3-C 6鹵環烷基、C 3-C 6環烷基C 1-C 6烷基、C 3-C 6鹵環烷基C 1-C 6烷基、氰基C 1-C 6烷基、未經取代或可選擇地經R 11取代之C 7-C 14芳烷基、或未經取代或可選擇地經R 11取代之C 6-C 14雜芳烷基, W 1代表氮原子, W 2代表碳原子,或 W 1代表碳原子, W 2代表氮原子, A 1代表氮原子、經R a取代之碳原子、或一鍵, A 2代表氮原子、經R b取代之碳原子、或一鍵, A 3代表氮原子、經R 3取代之碳原子、或一鍵, A 4、A 5、A 6、A 7、A 8及A 9各獨立地代表氮原子、或分別經R 4、R 5、R 6、R 7、R 8及R 9取代之碳原子, R a、R b、R 3、R 4、R 5、R 6、R 7、R 8及R 9各獨立地代表氫原子、鹵原子、疊氮基、氰基、硝基、C 1-C 6烷基、氰基C 1-C 6烷基、 羥基C 1-C 6烷基、C 1-C 6鹵烷基、C 2-C 6烯基、C 2-C 6炔基、C 3-C 6環烷基、氰基C 3-C 6環烷基、羥基C 3-C 6環烷基、C 3-C 6鹵環烷基、C 3-C 6環烷基C 1-C 6烷基、C 3-C 6環烷基C 2-C 6烯基、C 3-C 6環烷基C 2-C 6炔基、C 3-C 6鹵環烷基C 1-C 6烷基、未經取代或可選擇地經R 11取代之雜環基、未經取代或可選擇地經R 11取代之C 6-C 12芳基、未經取代或可選擇地經R 11取代之C 5-C 12雜芳基、未經取代或可選擇地經R 11取代之C 7-C 14芳烷基、未經取代或可選擇地經R 11取代之C 6-C 14雜芳烷基、羥基、C 1-C 6烷氧基、C 1-C 6鹵烷氧基、氰基C 1-C 6烷氧基、羥基C 1-C 6烷氧基、C 1-C 6鹵烷氧基C 1-C 6烷氧基、C 1-C 6烷氧基C 1-C 6鹵烷氧基、C 1-C 6鹵烷氧基C 1-C 6鹵烷氧基、C 3-C 6環烷氧基、C 3-C 6環烷基C 1-C 6烷氧基、C 3-C 6鹵環烷氧基、氰基C 3-C 6環烷氧基、C 3-C 6鹵環烷基C 1-C 6烷氧基、(氰基C 3-C 6環烷基)C 1-C 6烷氧基、C 1-C 6鹵烷基硫基C 1-C 6烷氧基、C 1-C 6鹵烷基亞磺醯基C 1-C 6烷氧基、C 1-C 6鹵烷基磺醯基C 1-C 6烷氧基、未經取代或可選擇地經R 11取代之C 7-C 14芳烷氧基、未經取代或可選擇地經R 11取代之C 6-C 14雜芳烷氧基、未經取代或可選擇地經R 11取代之C 6-C 12芳氧基、未經取代或可選擇地經R 11取代之C 5-C 12雜芳氧基、氫硫基、五鹵氫硫基、C 1-C 6烷基硫基、C 1-C 6烷基亞磺醯基、C 1-C 6烷基磺醯基、C 1-C 6鹵烷基硫基、C 1-C 6鹵烷基亞磺醯基、C 1-C 6鹵烷基磺醯基、C 3-C 6環烷基硫基、C 3-C 6環烷基亞磺醯基、C 3-C 6環烷基磺醯基、C 3-C 6鹵環烷基硫基、C 3-C 6鹵環烷基亞磺醯基、C 3-C 6鹵環烷基磺醯基、C 3-C 6環烷基C 1-C 6烷基硫基、C 3-C 6環烷基C 1-C 6烷基亞磺醯基、C 3-C 6環烷基C 1-C 6烷基磺醯基、C 3-C 6鹵環烷基C 1-C 6烷基硫基、C 3-C 6鹵環烷基C 1-C 6烷基亞磺醯基、C 3-C 6鹵環烷基C 1-C 6烷基磺醯基、基團-S (R 12) = NH、基團-S (R 12) = N-C≡N、基團-S (R 12) = N-C (= O) R 13、基團-S (R 12) (= O) = NH、基團-S (R 12) (= O) = N-C≡N、基團-S (R 12) (= O) = N-C (= O) R 13、C 6-C 12芳基硫基、C 6-C 12芳基亞磺醯基、C 6-C 12芳基磺醯基、C 5-C 12雜芳基硫基、C 5-C 12雜芳基亞磺醯基、C 5-C1 2雜芳基磺醯基、胺基、單(C 1-C 6烷基)胺基、二(C 1-C 6烷基)胺基、(二(C 1-C 6烷基)亞磺醯亞基)胺基、二(C 1-C 6烷基)磷醯基、C 1-C 7醯基、C 1-C 7鹵醯基、羥基亞胺基C 1-C 6烷基、羥基亞胺基(胺基)C 1-C 7烷基、C 1-C 6烷氧基亞胺基C 1-C 6烷基、C 1-C 6鹵烷氧基亞胺基C 1-C 6烷基、羧基、C 1-C 6烷氧基羰基、胺基羰基、單(C 1-C 6烷基)胺基羰基、二(C 1-C 6烷基)胺基羰基、單(C 1-C 6鹵烷基)胺基羰基、單(C 3-C 6環烷基)胺基羰基、單(氰基C 3-C 6環烷基)胺基羰基、單(C 1-C 6烷氧基亞胺基C 1-C 6烷基)胺基羰基、二(C 1-C 6烷基)胺基亞甲基 胺基羰基、胺基硫羰基、單(C 1-C 6烷基)胺基硫羰基、二(C 1-C 6烷基)胺基硫羰基、或N-(C 1-C 6烷氧基)-N-(C 1-C 6烷基)胺基羰基, R 10代表氫原子、C 1-C 12烷基、C 1-C 6烷氧基C 1-C 6烷基、C 1-C 12鹵烷基、C 1-C 6烷氧基C 1-C 6鹵烷基、C 1-C 6鹵烷氧基C 1-C 6烷基、C 1-C 6鹵烷氧基 C 1-C 6鹵烷基、C 2-C 6烯基、C 2-C 6鹵烯基、C 2-C 6炔基、C 3-C 6環烷基C 2-C 6炔基、C 2-C 6鹵炔基、C 3-C 6環烷基、C 3-C 6鹵環烷基、C 3-C 6環烷基C 1-C 6烷基、C 3-C 6鹵環烷基C 1-C 6烷基、未經取代或可選擇地經R 11取代之雜環基C 1-C 6烷基、未經取代或可選擇地經R 11取代之C 7-C 14芳烷基、未經取代或可選擇地經R 11取代之C 6-C 14雜芳烷基、未經取代或可選擇地經R 11取代之C 6-C 12芳基、或未經取代或可選擇地經R 11取代之C 5-C 12雜芳基,及 R 11代表鹵原子、疊氮基、氰基、硝基、C 1-C 6烷基、C 1-C 6鹵烷基、C 1-C 6烷氧基、C 1-C 6鹵烷氧基、C 3-C 6環烷基、五鹵氫硫基、C 1-C 6烷基硫基、C 1-C 6烷基亞磺醯基、C 1-C 6烷基磺醯基、C 1-C 6鹵烷基硫基、C 1-C 6鹵烷基亞磺醯基、C 1-C 6鹵烷基磺醯基、胺基、單(C 1-C 6烷基)胺基、或二(C 1-C 6烷基)胺基, R 12及R 13獨立地代表C 1-C 6烷基、C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6鹵烷基、C 1-C 6烷氧基C 1-C 6鹵烷基、C 1-C 6鹵烷氧基C 1-C 6烷基、C 1-C 6鹵烷氧基C 1-C 6鹵烷基、C 3-C 6環烷基、C 3-C 6鹵環烷基、C 3-C 6環烷基C 1-C 6烷基、C 3-C 6鹵環烷基C 1-C 6烷基、氰基C 1-C 6烷基、未經取代或可選擇地經R 11取代之C 7-C 14芳烷基、或未經取代或可選擇地經R 11取代之C 6-C 14雜芳烷基。
- 如請求項1之化合物或其鹽,其中A 7代表氮原子,且A 8及A 9各代表分別經R 8及R 9取代之碳原子。
- 如請求項1之化合物或其鹽,其中A 1代表一鍵, A 2及A 7各代表氮原子, W 1代表氮原子, W 2代表碳原子,且 A 3、A 4、A 5、A 6、A 8及A 9各代表分別經R 3、R 4、R 5、R 6、R 8及R 9取代之碳原子。
- 如請求項3之化合物或其鹽,其中R 3、R 4、R 5、R 6、R 8及R 9各獨立地代表氫原子、鹵原子、C 1-C 6烷基、C 1-C 6鹵烷基、氰基C 3-C 6環烷基、C 1-C 6鹵烷氧基,或氰基C 1-C 6烷氧基。
- 如請求項1至4中任一項之化合物或其鹽,其中R 2代表C 1-C 6烷基。
- 如請求項1至5中任一項之化合物或其鹽,其中R 10代表C 1-C 12鹵烷基。
- 如請求項8之化合物或其鹽,其中n為2,R 3、R 5及R 6各為氫原子,R 4為C 1-C 6鹵烷基、氰基C 3-C 6環烷基、C 1-C 6鹵烷氧基、或氰基C 1-C 6烷氧基,且R 10為C 1-C 12鹵烷基。
- 如請求項12之化合物或其鹽,其中A 2代表經R b取代之氮原子或碳原子,A 3代表經R 3取代之氮原子或碳原子,且A 4、A 5及A 6各獨立地代表分別經R 4、R 5及R 6取代之氮原子或碳原子。
- 一種殺蟲劑組成物,其包含如請求項1至13之化合物或其鹽作為活性成分。
- 如請求項14之殺蟲劑組成物,其中該殺蟲劑組成物進一步包含表面活性劑。
- 一種害蟲防治劑,其包含如請求項1至13之化合物或其鹽作為活性成分。
- 如請求項16之害蟲防治劑,其中該害蟲防治劑為殺蟲劑、殺線蟲劑或殺蟎劑。
- 如請求項17之害蟲防治劑,其對於在水田、農地、草坪、果園、非農用地、溫室、苗圃設施、種植農業及園藝植物的植物工廠具有防治害蟲效果。
- 如請求項18之害蟲防治劑,其中該農業及園藝植物是藉由育種方法或基因重組技術產生抗性的植物。
- 一種防治害蟲之方法,其使用有效量之如請求項1至13之化合物或其鹽。
- 一種防治害蟲之方法,其藉由使包含如請求項1至13之化合物或其鹽作為活性成分的殺蟲劑組成物以同時或分次作用於欲生長或正在生長之農作物或園藝作物的場所來防治害蟲。
- 如請求項20或21之防治害蟲之方法,其中該害蟲防治劑施用的場所為水田、農地、草坪、果園、非農用地、溫室、苗圃設施或植物工廠。
- 如請求項20至22中任一項之防治害蟲之方法,其中該如請求項1至13之化合物或其鹽用作殺蟲劑、殺線蟲劑或殺蟎劑。
- 一種如請求項16至19之害蟲防治劑用於在農作物或園藝作物上防治害蟲的用途。
- 如請求項1之通式[I]代表之化合物或其鹽,其中在通式[I]中之R 10為氫原子。
- 一種製造如請求項1之通式[I]代表的化合物之方法,其包含使用如請求項25之化合物或其鹽作為中間體。
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JPH0348081A (ja) | 1989-07-10 | 1991-03-01 | Nippondenso Co Ltd | 三方電磁弁 |
WO2003048081A2 (en) | 2001-12-04 | 2003-06-12 | Bristol-Myers Squibb Company | Glycinamides as factor xa inhibitors |
FR2928923B1 (fr) | 2008-03-21 | 2010-04-23 | Sanofi Aventis | Derives polysubstitues de 2-heteroaryl-6-phenyl-imidazo °1,2-a!pyridines, leur preparation et leur application en therapeutiques |
KR20210057223A (ko) | 2009-06-17 | 2021-05-20 | 바이오젠 엠에이 인코포레이티드 | 대상에게서 smn2 스플라이싱을 조정하기 위한 조성물 및 방법 |
WO2011135496A2 (en) | 2010-04-25 | 2011-11-03 | Objet Geometries Ltd. | Solid freeform fabrication of shelled objects |
AU2013336755B2 (en) | 2012-10-24 | 2017-07-20 | Basf Se | Herbicidal azines |
GB201318863D0 (en) | 2013-10-25 | 2013-12-11 | Syngenta Ltd | Herbicidal compounds |
US9999222B2 (en) | 2014-04-23 | 2018-06-19 | Basf Se | Herbicidal combination comprising azines |
JP6422814B2 (ja) | 2015-04-16 | 2018-11-14 | 学校法人北里研究所 | デカルバモイルサキシトキシン及びその類縁体の製造方法 |
CN107635967B (zh) | 2015-06-18 | 2021-03-26 | 日本曹达株式会社 | 二芳基唑化合物和有害生物防除剂 |
WO2017061497A1 (ja) | 2015-10-06 | 2017-04-13 | 日本農薬株式会社 | 縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 |
JP6855504B2 (ja) | 2016-04-15 | 2021-04-07 | シンジェンタ パーティシペーションズ アーゲー | 除草性ピリダジノン化合物 |
GB201612748D0 (en) | 2016-07-22 | 2016-09-07 | Syngenta Participations Ag | Method of controlling plants |
AU2017327309A1 (en) | 2016-09-16 | 2019-04-04 | Sumitomo Chemical Company, Limited | Heterocyclic compound, and harmful-arthropod-controlling agent containing same |
UA126681C2 (uk) | 2017-06-13 | 2023-01-11 | Баєр Акціенгезельшафт | Гербіцидно активний 3-фенілізоксазолін-5-карбоксамід амідів тетрагідро- та дифуранкарбонових кислот |
JP7253498B2 (ja) | 2017-12-22 | 2023-04-06 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除剤 |
JP6456530B1 (ja) | 2018-01-16 | 2019-01-23 | 株式会社アペレ | 血液凝固時間測定用カートリッジ及び血液凝固時間測定装置 |
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JP2022185597A (ja) * | 2019-10-31 | 2022-12-15 | クミアイ化学工業株式会社 | アゾール誘導体及びその用途 |
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JP2020105188A (ja) * | 2020-03-02 | 2020-07-09 | 住友化学株式会社 | 複素環化合物を用いる有害節足動物防除方法 |
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CN117098759A (zh) | 2023-11-21 |
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WO2022210999A1 (ja) | 2022-10-06 |
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AU2022250255A1 (en) | 2023-10-19 |
JPWO2022210999A1 (zh) | 2022-10-06 |
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