TW201839002A - 作為殺蟲劑之稠合雙環雜環衍生物 - Google Patents
作為殺蟲劑之稠合雙環雜環衍生物 Download PDFInfo
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- TW201839002A TW201839002A TW107113482A TW107113482A TW201839002A TW 201839002 A TW201839002 A TW 201839002A TW 107113482 A TW107113482 A TW 107113482A TW 107113482 A TW107113482 A TW 107113482A TW 201839002 A TW201839002 A TW 201839002A
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- alkyl
- cycloalkyl
- spp
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- alkoxy
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- 125000002618 bicyclic heterocycle group Chemical group 0.000 title abstract description 6
- 239000000575 pesticide Substances 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 229
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 238000009472 formulation Methods 0.000 claims abstract description 67
- 241001465754 Metazoa Species 0.000 claims abstract description 43
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 33
- 239000003905 agrochemical Substances 0.000 claims abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 313
- -1 (C 3 -C 8) - cycloalkyl amine Chemical class 0.000 claims description 226
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 180
- 239000001257 hydrogen Substances 0.000 claims description 125
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 118
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 112
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 103
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 102
- 229910052757 nitrogen Inorganic materials 0.000 claims description 97
- 229910052736 halogen Inorganic materials 0.000 claims description 90
- 150000002367 halogens Chemical class 0.000 claims description 89
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 80
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 73
- 229910052760 oxygen Inorganic materials 0.000 claims description 73
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 70
- 239000001301 oxygen Substances 0.000 claims description 70
- 229910052717 sulfur Inorganic materials 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 64
- 239000011593 sulfur Substances 0.000 claims description 63
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 62
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 125000002252 acyl group Chemical group 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- 229910052799 carbon Inorganic materials 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 25
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 23
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 17
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 16
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 16
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 12
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims description 11
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003852 triazoles Chemical class 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000002619 bicyclic group Chemical group 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
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- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 8
- 239000004606 Fillers/Extenders Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims description 7
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 7
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
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- 150000001266 acyl halides Chemical class 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- KJMXVHBTWJSSBL-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-imidazole Chemical compound FC(F)(F)C1=NC=CN1 KJMXVHBTWJSSBL-UHFFFAOYSA-N 0.000 claims description 4
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
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- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
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Abstract
Description
本發明係關於新穎式(I)稠合雙環雜環衍生物、含式(I)化合物之農化調配物及其作為殺蟎劑及/或殺昆蟲劑用途以控制動物害蟲,尤其是節肢動物,糗特別是昆蟲及蛛形綱動物。
具有殺昆蟲特性之稠合雙環雜環衍生物已被揭示於文獻中,例如於WO 2010/125985、WO 2013/180193、WO 2016/039444、WO 2016/129684、WO 2016/142327、WO 2016/169882、WO 2016/169886、WO 2017/001311、WO 2016/162318、WO 2017/093180、WO 2017/125340、WO 2017/144341、EP16184163.0、EP 16189445.6及EP 16200177.0。
現代殺昆蟲劑及殺蟎劑必須符合許多要求,例如關於其作用及可能之用途的限度、持續性及廣度。毒性問題、對有益物種和授粉者的節制使用、環境特性、施用率、與其他活性成分或調配物助劑的組合這些所提的幾個參數扮演一定的角色,活性成分合成中涉及的複雜問題也會是個問題,而且還可能發生抗性。僅就所有這些原因而言,對新穎作物保護組成物的研究不能被認為是完整的,而且與已知化合物相比,至少就個別方面而言, 不斷需要具有改進的特性的新穎化合物。
本發明的目的在提供用於控制動物害蟲的化合物,其化合物在各個方面擴大了殺蟲劑的範圍。
現已發現新穎稠合雙環雜環衍生物,其具有超越已知化合物的優點,實例包括生物或環境特性、更廣泛的應用方法、更佳的殺昆蟲或殺蟎作用以及與作物植物的良好的相容性。稠合雙環雜環衍生物可與其他藥物組合使用以提高效力,尤其是對抗難以控制的昆蟲。
因此,本發明之標的為新穎式(I)化合物
另發現式(I)化合物作為殺蟲劑具有非常好的功效,較佳作為殺昆蟲劑及/或殺蟎劑,且另外一般具有非常好的植物相容性,特別是關於作物植物。
本發明化合物一般由式(I)定義,在上下文提及的化學式中給定的較佳取代基或殘基範圍在下文中說明:
式(I)化合物,其中較佳地 在代表單鍵及雙鍵之情況下,且Aa至Ae因此形成芳香環, Aa 代表氮或碳,Ab 代表氮、氧、硫、N(R8)或C(R11),Ac 代表氮、氧、硫或C(R12),Ad 代表氮、氧、硫、N(R8)或C(R13),Ae 代表氮或碳,其中R8 代表甲基、乙基、環丙基或氫,且其中基團Aa、Ab、Ac、Ad和Ae中至多三個可代表氮,且基團Ab、Ac和Ad中至多一個可代表氧,或基團Ab、Ac和Ad中至多一個可代表硫,或Ab和Ad中至多一個可以代表N(R8), 或,若僅代表單鍵, Aa 代表碳,Ab 代表硫、氧或C(R11)(R15),Ac 代表硫、氧或C(R12)(R16),且Ad 代表硫、氧或C(R13)(R17),Ae 代表碳,其中基團Aa、Ab、Ac、Ad及Ae中至多一個可代表氧或硫,R1 較佳地代表(C1-C4)-烷基、(C1-C4)-羥基烷基、(C1-C4)-鹵烷基、(C2-C4)-烯基、(C2-C4)-鹵烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C3-C6)-環烷基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-鹵烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基或(C1-C4)-烷基磺醯基-(C1-C4)-烷基, R11、R12、R13、R15、R16、R17 彼此獨立較佳地代表氫、氰基、鹵素、硝基、羥基、胺基、三-(C1-C4)-烷基矽烷基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-羥基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-鹵烯基、(C2-C4)-氰基烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C2-C4)-氰基炔基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、(C1-C4)-氰基烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、(C1-C4)-烷基羥基亞胺基、(C1-C4)-烷氧基亞胺基、(C1-C4)-烷基-(C1-C4)-烷氧基亞胺基、(C1-C4)-鹵烷基-(C1-C4)-烷氧基亞胺基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯氧基、(C1-C4)-烷基羰基、(C1-C4)-鹵烷基羰基、胺基羰基、胺基硫基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基磺醯基胺基、(C1-C4)-烷基胺基、二-(C1-C4)-烷基胺基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基、胺基硫基羰基、(C1-C4)-烷基羰基胺基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、(C1-C4)-烷基羰基-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CO-(C1-C6)-烷基)、((C1-C4)-烷氧基羰基)胺基(-NHCOO-(C1-C4)-烷基)、((C1-C4)-烷氧基羰基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-COO-(C1-C6)-烷基)、(C1-C4)- 烷基胺甲醯氧基(-OCONH-(C1-C4)-烷基)、二-(C1-C4)-烷基胺甲醯氧基(-OCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)胺基(-NHCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CON-(C1-C4)-二烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C4)-烷基胺基(-N(C1-C4)-烷基-CONH2)或較佳地代表苯基或5-或6-員雜芳基,其各可選擇地經相同或不同之取代基單取代-或多取代,其中(在雜芳基之情況下)可選擇地存在至少一個羰基基團,且該雜原子選自N、S及O,且其中在各情況中可能之取代基如下:氰基、鹵素、乙醯基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C2-(C1-C4)-烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯氧基、(C1-C4)-烷基羰基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基磺醯基胺基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基或(C1-C4)-烷基羰基胺基, 其中該基團R11、R12、R13、R15、R16、R17中至多二個代表氫以外之取代基,且,在R11及R15、R12及R16或R13及R17不代表氫的情況下,R15、R16及R17各彼此獨立僅代表氰基、鹵素、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基或(C1-C4)-氰基烷基, 或,在僅代表單鍵之情況,在各情況中另外R11及R15及/或R13 及R17一起較佳地代表氧(=O),Q 較佳地代表Q1至Q13及Q15至Q21所組成之雜芳族9-員或12-員稠合雙環或三環系統
其中R4 較佳地代表(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-羥基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-鹵烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-烯氧基-(C1-C4)-烷基、(C2-C4)-鹵烯氧基-(C1-C4)-烷基、(C2-C4)-鹵烯基、(C2-C4)-氰基烯基、(C2-C4)-炔基、 (C2-C4)-炔氧基-(C1-C4)-烷基、(C2-C4)-鹵炔基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯基-(C1-C4)-烷基或(C1-C4)-烷基羰基-(C1-C4)-烷基,R5、R6 彼此獨立較佳地代表氫、氰基、鹵素、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C2-C4)-烯基、(C2-C4)-鹵烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、(C1-C4)-烷氧基亞胺基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯氧基、(C1-C4)-烷基羰基、(C1-C4)-鹵烷基羰基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基磺醯基胺基、(C1-C4)-烷基胺基、二-(C1-C4)-烷基胺基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基或可選擇地經單氰基-取代之(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基或(C1-C4)-烷基-(C3-C6)-環烷基,R7 較佳地代表氫、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-羥基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-鹵烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-烯氧基-(C1-C4)-烷基、(C2-C4)-鹵烯氧基-(C1-C4)-烷基、(C2-C4)-鹵烯基、(C2-C4)-氰基烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基硫 基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基或(C1-C4)-烷基磺醯基-(C1-C4)-烷基,及n 較佳為0、1或2。
式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物,
其中R1 特佳地代表(C1-C4)-烷基、(C1-C4)-鹵烷基或(C3-C6)-環烷基,R8 特佳地代表甲基、乙基、環丙基或氫, R11、R12、R13、R15、R16、R17 彼此獨立特佳地代表氫、氰基、鹵素、硝基、羥基、(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、(C1-C4)-烷基羰基-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CO-(C1-C6)-烷基)、((C1-C4)-烷氧基羰基)胺基(-NHCOO-(C1-C4)-烷基)、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)胺基(-NHCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N(C1-C4)-烷基-CONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N(C1-C4)-烷基-CON-(C1-C4)-二烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH2)或特佳地代表苯基、三唑或吡唑,其各可選擇地經相同或不同之取代基單取代-或雙取代,在各情況中可能的取代基為:氰基、鹵素、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C1-C4)-烷氧基、(C1-C4)-烷基 硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯氧基、(C1-C4)-烷基羰基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基磺醯基胺基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基或(C1-C4)-烷基羰基胺基,其中基團R11、R12、R13、R15、R16、R17中至多二個代表氫以外的取代基,且,在R11及R15、R12及R16或R13及R17不代表氫的情況下,R14、R15、R16及R17各彼此獨立僅代表氰基、鹵素、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基或(C1-C4)-鹵烷基,或,在結構式(In)至(It)之情況,R11及R15或R13及R17另在各情況中一起特佳地代表氧(=O),Q 特佳地代表Q1、Q2、Q3、Q5、Q6、Q8、Q9、Q10、Q12、Q15、Q20及Q21所組成群組之雜芳族9-員稠合雙環環系統,
R4 特佳地代表(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,R5 特佳地代表鹵素、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-鹵烷基磺醯基或代表可選擇地經單氰基-取代之(C3-C6)-環烷基,R6 特佳地代表氫、氰基、鹵素或(C1-C4)-烷基,R7 特佳地代表氫、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-羥基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-鹵烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-烯氧基-(C1-C4)-烷基、(C2-C4)-鹵烯氧基-(C1-C4)-烷基、(C2-C4)-鹵烯基、(C2-C4)-氰基烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基硫 基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基或(C1-C4)-烷基磺醯基-(C1-C4)-烷基,及n 特佳地代表0、1或2。
非常特佳為給予式(Ia)、(Ib)、(Id)、(Ie)、(Ii)至(Ik)、(In)、(Iq)及(Ir)化合物
其中R1 非常特佳地代表(C1-C4)-烷基、(C3-C6)-環烷基或(C1-C4)-鹵烷基,R13、R15、R16、R17 彼此獨立非常特佳地代表氫、鹵素、(C1-C4)-鹵烷基或(C1-C4)-烷基,R11、R12 彼此獨立非常特佳地代表氫、氰基、鹵素、硝基、羥基、(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)- 烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、(C1-C4)-烷基羰基-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CO-(C1-C6)-烷基)、((C1-C4)-烷氧基羰基)胺基(-NHCOO-(C1-C4)-烷基)、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)胺基(-NHCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N(C1-C4)-烷基-CONH-(C1-C4)-烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH2)或非常特佳地代表苯基、吡唑或三唑,其各可選擇地經相同或不同之取代基單取代-或雙取代,在各情況中可能的取代基為:氰基、鹵素、(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯氧基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基羰基胺基,其中基團R11、R12、R13、R15、R16、R17中至多二個代表氫以外的取代基,且,在R11及R15、R12及R16或R13及R17不代表氫的情況下,R14、R15、R16 及R17各彼此獨立僅代表鹵素、(C1-C4)-鹵烷基或(C1-C4)-烷基,或,在結構式(In)、(Iq)及(Ir)之情況,R11及R15或R13及R17另在各情況中一起非常特佳地代表氧(=O),Q 非常特佳地代表Q1、Q2、Q3、Q5、Q6、Q12、Q10、Q15、Q20及Q21所組成群組之雜芳族9-員稠合雙環環系統,
其中R4 非常特佳地代表(C1-C4)-烷基,R5 非常特佳地代表鹵素、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-鹵烷基亞磺醯基或代表可選擇地經單氰基-取代之(C3-C6)-環烷基,R6 非常特佳地代表氫, R7 非常特佳地代表氫、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-鹵烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-鹵烯基、(C2-C4)-氰基烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基或(C1-C4)-烷基磺醯基-(C1-C4)-烷基,及n 甚佳為0、1或2。
重要的是給予式(Ia)、(Id)、(Ij)及(In)化合物,
其中R1 最佳地代表(C1-C4)-烷基,R13 最佳地代表氫或鹵素,R15、R16、R17 最佳地代表氫,R11、R12 彼此獨立最佳地代表氫、羥基、氰基、鹵素、(C1-C4)-烷基、(C3-C6)-環烷基、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、 (N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、苯基,或代表吡唑或三唑,其各可選擇地經(C1-C4)-烷基、鹵素或(C1-C4)-鹵烷基單取代,或,在結構式(In)情況中,R11及R15或R13及R17另在各情況中一起最佳地代表氧(=O),Q 最佳地代表Q2、Q3、Q15及Q21所組成群組之雜芳族9-員稠合雙環環系統,
R4 最佳地代表(C1-C4)-烷基,R5 最佳地代表(C1-C4)-鹵烷基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-鹵烷基亞磺醯基或經單氰基-取代之環丙基,R6 最佳地代表氫,且R7 最佳地代表(C1-C4)-烷基、環丙基、甲氧基甲基或甲氧基乙基,且n 最佳地代表0或2。
重要的是給予式(Ia)、(Id)、(Ij)及(In)化合物,
其中 R1 尤其是代表乙基,R13 尤其是代表氫或氟,R15、R16、R17 尤其是代表氫,R11 尤其是代表氫、羥基、氰基、環丙基、三氟甲基、溴、碘、氟、胺基羰基、甲基胺基羰基、甲基羰基胺基、環丙基羰基胺基、(N-甲基胺甲醯基)胺基(-NHCONHMe)、苯基、N-甲基吡唑、三氟甲基咪唑或氯吡唑,R12 尤其是代表氫、環丙基、甲基、三氟甲基或氯,或,在結構式(In)之情況,R11及R15或R13及R17另在各情況中尤其是一起代表氧(=O),Q 尤其是代表Q2、Q3、Q15及Q21所組成群組之雜芳族9-員稠合雙環環系統,
R4 尤其是代表甲基,R5 尤其是代表三氟甲基、三氟甲基磺醯基、三氟甲基硫基、三氟甲基亞磺醯基或五氟乙基,R6 尤其是代表氫,R7 尤其是代表甲基且n 尤其是代表2。
式(I)的其他替代具體實施例如下所示:式(I)化合物
其中代表二個單鍵或一個雙鍵及一個單鍵, 其中(組態1-2) 若代表雙鍵及單鍵,且Aa至Ae因此形成芳香環, Aa 代表氮或碳,Ab 代表氮、氧、硫或C(R11),Ac 代表氮、氧、硫或C(R12),Ad 代表氮、氧、硫或C(R13),Ae 代表氮或碳,其中基團Aa、Ab、Ac、Ad及Ae中至多三個可代表氮且至多一個可代表氧或至多一個可代表代表硫, 或在僅代表單鍵之情況, Aa 代表碳,Ab 代表硫、氧或C(R11)(R15),Ac 代表硫、氧或C(R12)(R16)且Ad 代表硫、氧或C(R13)(R17),Ae 代表碳,其中基團Aa、Ab、Ac、Ad及Ae中至多一個可代表氧或硫, R1 代表(C1-C6)-烷基、(C1-C6)-鹵烷基、(C1-C6)-氰基烷基、(C1-C6)-羥基烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-鹵烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-烯氧基-(C1-C6)-烷基、(C2-C6)-鹵烯氧基-(C1-C6)-烷基、(C2-C6)-鹵烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-炔氧基-(C1-C6)-烷基、(C2-C6)-鹵炔氧基-(C1-C6)-烷基、(C2-C6)-鹵炔基、(C2-C6)-氰基炔基、(C3-C8)-環烷基、(C3-C8)-環烷基-(C3-C8)-環烷基、(C1-C6)-烷基-(C3-C8)-環烷基、鹵-(C3-C8)-環烷基、胺基、(C1-C6)-烷基胺基、二-(C1-C6)-烷基胺基、(C3-C8)-環烷基胺基、(C1-C6)-烷基羰基胺基、(C1-C6)-烷基硫基-(C1-C6)-烷基、(C1-C6)-鹵烷基硫基-(C1-C6)-烷基、(C1-C6)-烷基亞磺醯基-(C1-C6)-烷基、(C1-C6)-鹵烷基亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷基磺醯基-(C1-C6)-烷基、(C1-C6)-鹵烷基磺醯基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基硫基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基磺醯基-(C1-C6)-烷基、(C1-C6)-烷基羰基-(C1-C6)-烷基、(C1-C6)-鹵烷基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-鹵烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷基磺醯基胺基、胺基磺醯基-(C1-C6)-烷基、(C1-C6)-烷基胺基磺醯基-(C1-C6)-烷基、二-(C1-C6)-烷基胺基磺醯基-(C1-C6)-烷基,或代表(C1-C6)-烷基、(C1-C6)-烷氧基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C8)-環烷基,其各可選擇地經芳基、雜芳基及雜環基所組成群組之相同或不同之取代基單取代-或多取代,其中芳基、雜芳基或雜環基可各別可選擇地經下列所組成群組之相同或不同之取代基單取代-或 多取代:鹵素、氰基、硝基、羥基、胺基、羧基、胺甲醯基、胺基磺醯基、(C1-C6)-烷基、(C3-C6)-環烷基、(C1-C6)-烷氧基、(C1-C6)-鹵烷基、(C1-C6)-鹵烷氧基、(C1-C6)-烷基硫基、(C1-C6)-烷基亞磺醯基、(C1-C6)-烷基磺醯基、(C1-C6)-烷基硫亞胺基、(C1-C6)-烷基硫亞胺基-(C1-C6)-烷基、(C1-C6)-烷基硫亞胺基-(C2-C6)-烷基羰基、(C1-C6)-烷基亞碸醯亞胺基、(C1-C6)-烷基亞碸醯亞胺基-(C1-C6)-烷基、(C1-C6)-烷基亞碸醯亞胺基-(C2-C6)-烷基羰基、(C1-C6)-烷氧基羰基、(C1-C6)-烷基羰基、(C3-C6)-三烷基矽烷基及苄基,或R1 代表芳基、雜芳基或雜環基,其各可選擇地經下列所組成群組之相同或不同之取代基單取代-或多取代:鹵素、氰基、硝基、羥基、胺基、羧基、胺甲醯基、(C1-C6)-烷基、(C3-C8)-環烷基、(C1-C6)-烷氧基、(C1-C6)-鹵烷基、(C1-C6)-鹵烷氧基、(C1-C6)-烷基硫基、(C1-C6)-烷基亞磺醯基、(C1-C6)-烷基磺醯基、(C1-C6)-烷基硫亞胺基、(C1-C6)-烷基硫亞胺基-(C1-C6)-烷基、(C1-C6)-烷基硫亞胺基-(C2-C6)-烷基羰基、(C1-C6)-烷基亞碸醯亞胺基、(C1-C6)-烷基亞碸醯亞胺基-(C1-C6)-烷基、(C1-C6)-烷基亞碸醯亞胺基-(C2-C6)-烷基羰基、(C1-C6)-烷氧基羰基、(C1-C6)-烷基羰基、(C3-C6)-三烷基矽烷基、(=O)(only in the case of雜環基)及(=O)2(僅在雜環基之情況),R11、R12、R13、R15、R16、R17 彼此獨立代表氫、氰基、鹵素、硝基、羥基、胺基、三-(C1-C6)-烷基矽烷基、(C3-C8)-環烷基、(C3-C8)-環烷基-(C3-C8)-環烷基、(C1-C6)-烷基-(C3-C8)-環烷基、鹵-(C3-C8)-環烷基、(C1-C6)-烷基、(C1-C6)-鹵烷基、(C1-C6)-氰基烷基、(C1-C6)-羥基烷基、羥基羰基 -(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-鹵烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-鹵炔基、(C2-C6)-氰基炔基、(C1-C6)-烷氧基、(C1-C6)-鹵烷氧基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羥基亞胺基、(C1-C6)-烷氧基亞胺基、(C1-C6)-烷基-(C1-C6)-烷氧基亞胺基、(C1-C6)-鹵烷基-(C1-C6)-烷氧基亞胺基、(C1-C6)-烷基硫基、(C1-C6)-鹵烷基硫基、(C1-C6)-烷氧基-(C1-C6)-烷基硫基、(C1-C6)-烷基硫基-(C1-C6)-烷基、(C1-C6)-烷基亞磺醯基、(C1-C6)-鹵烷基亞磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷基亞磺醯基、(C1-C6)-烷基亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷基磺醯基、(C1-C6)-鹵烷基磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷基磺醯基、(C1-C6)-烷基磺醯基-(C1-C6)-烷基、(C1-C6)-烷基磺醯氧基、(C1-C6)-烷基羰基、(C1-C6)-烷基硫基羰基、(C1-C6)-鹵烷基羰基、(C1-C6)-烷基羰氧基、(C1-C6)-烷氧基羰基、(C1-C6)-鹵烷氧基羰基、胺基羰基、(C1-C6)-烷基胺基羰基、(C1-C6)-烷基胺基硫基羰基、二-(C1-C6)-烷基胺基羰基、二-(C1-C6)-烷基胺基硫基羰基、(C2-C6)-烯基胺基羰基、二-(C2-C6)-烯基胺基羰基、(C3-C8)-環烷基胺基羰基、(C1-C6)-烷基磺醯基胺基、(C1-C6)-烷基胺基、二-(C1-C6)-烷基胺基、(C3-C8)-環烷基胺基、胺基磺醯基、(C1-C6)-烷基胺基磺醯基、二-(C1-C6)-烷基胺基磺醯基、(C1-C6)-烷基亞碸醯亞胺基、胺基硫基羰基、(C1-C6)-烷基胺基硫基羰基、二-(C1-C6)-烷基胺基硫基羰基、(C1-C6)-烷基羰基胺基(-NHCO-(C1-C6)-烷基)、(C3-C8)-環烷基羰基胺基、(C1-C6)-烷基羰基 -(C1-C6)-烷基胺基(-N(C1-C6)-烷基-CO-(C1-C6)-烷基)、((C1-C6)-烷氧基羰基)胺基(-NHCOO-(C1-C6)-烷基)、((C1-C6)-烷氧基羰基)-(C1-C6)-烷基胺基(-N-(C1-C6)-烷基-COO-(C1-C6)-烷基)、(C1-C6)-烷基胺甲醯氧基(-OCONH-(C1-C6)-烷基)、二-(C1-C6)-烷基胺甲醯氧基(-OCON-(C1-C6)-二烷基)、(N-(C1-C6)-烷基胺甲醯基)胺基(-NHCONH-(C1-C6)-烷基)、(N,N-二-(C1-C6)-烷基胺甲醯基)胺基(-NHCON-(C1-C6)-二烷基)、(N-(C1-C6)-烷基胺甲醯基)-(C1-C6)-烷基胺基(-N(C1-C6)-烷基-CONH-(C1-C6)-烷基)、(N,N-二-(C1-C6)-烷基胺甲醯基)-(C1-C6)-烷基胺基(-N-(C1-C6)-烷基-CON-(C1-C6)-二烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C6)-烷基胺基(-N-(C1-C6)-烷基-CONH2)或代表芳基或雜芳基,其各可選擇地經相同或不同之取代基單取代-或多取代,其中(在雜芳基之情況下)可選擇地存在至少一個羰基基團且其中可能的取代基在各情況中如下:氰基、羧基、鹵素、硝基、羥基、胺基、三-(C1-C6)-烷基矽烷基、(C3-C8)-環烷基、(C3-C8)-環烷基-(C3-C8)-環烷基、(C1-C6)-烷基-(C3-C8)-環烷基、鹵-(C3-C8)-環烷基、(C1-C6)-烷基、(C1-C6)-鹵烷基、(C1-C6)-氰基烷基、(C1-C6)-羥基烷基、羥基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-鹵烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-鹵炔基、(C2-C6)-氰基炔基、(C1-C6)-烷氧基、(C1-C6)-鹵烷氧基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羥基亞胺基、 (C1-C6)-烷氧基亞胺基、(C1-C6)-烷基-(C1-C6)-烷氧基亞胺基、(C1-C6)-鹵烷基-(C1-C6)-烷氧基亞胺基、(C1-C6)-烷基硫基、(C1-C6)-鹵烷基硫基、(C1-C6)-烷氧基-(C1-C6)-烷基硫基、(C1-C6)-烷基硫基-(C1-C6)-烷基、(C1-C6)-烷基亞磺醯基、(C1-C6)-鹵烷基亞磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷基亞磺醯基、(C1-C6)-烷基亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷基磺醯基、(C1-C6)-鹵烷基磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷基磺醯基、(C1-C6)-烷基磺醯基-(C1-C6)-烷基、(C1-C6)-烷基磺醯氧基、(C1-C6)-烷基羰基、(C1-C6)-鹵烷基羰基、(C1-C6)-烷基羰氧基、(C1-C6)-烷氧基羰基、(C1-C6)-鹵烷氧基羰基、胺基羰基、(C1-C6)-烷基胺基羰基、二-(C1-C6)-烷基胺基羰基、(C2-C6)-烯基胺基羰基、二-(C2-C6)-烯基胺基羰基、(C3-C8)-環烷基胺基羰基、(C1-C6)-烷基磺醯基胺基、(C1-C6)-烷基胺基、二-(C1-C6)-烷基胺基、胺基磺醯基、(C1-C6)-烷基胺基磺醯基、二-(C1-C6)-烷基胺基磺醯基、(C1-C6)-烷基亞碸醯亞胺基、胺基硫基羰基、(C1-C6)-烷基胺基硫基羰基、二-(C1-C6)-烷基胺基硫基羰基、(C3-C8)-環烷基胺基或(C1-C6)-烷基羰基胺基,其中基團R11、R12、R13、R15、R16、R17中僅一或二個代表氫以外的取代基,且在R11及R15、R12及R16或R13及R17不代表氫之情況,R15、R16及R17 各彼此獨立僅代表氰基、鹵素、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基或(C1-C4)-氰基烷基,Q 代表部分飽和或飽和雜環或雜芳族8-、9-、10-、11-或12-員稠合雙環或三環系統,其可選擇地包括至少一個羰基基團及/或,其中該環系統 可選擇地經相同或不同之取代基單取代-或多取代,其中該取代基彼此獨立可被選自氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C1-C6)-烷基矽烷基、(C3-C8)-環烷基、(C3-C8)-環烷基-(C3-C8)-環烷基、(C1-C6)-烷基-(C3-C8)-環烷基、鹵-(C3-C8)-環烷基、(C1-C6)-烷基、(C1-C6)-鹵烷基、(C1-C6)-氰基烷基、(C1-C6)-羥基烷基、羥基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-鹵烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-炔氧基-(C1-C4)-烷基、(C2-C6)-鹵炔基、(C2-C6)-氰基炔基、(C1-C6)-烷氧基、(C1-C6)-鹵烷氧基、(C1-C6)-鹵烷氧基-(C1-C6)-烷基、(C2-C6)-烯氧基-(C1-C6)-烷基、(C2-C6)-鹵烯氧基-(C1-C6)-烷基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羥基亞胺基、(C1-C6)-烷氧基亞胺基、(C1-C6)-烷基-(C1-C6)-烷氧基亞胺基、(C1-C6)-鹵烷基-(C1-C6)-烷氧基亞胺基、(C1-C6)-烷基硫基、(C1-C6)-鹵烷基硫基、(C1-C6)-烷氧基-(C1-C6)-烷基硫基、(C1-C6)-烷基硫基-(C1-C6)-烷基、(C1-C6)-烷基亞磺醯基、(C1-C6)-鹵烷基亞磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷基亞磺醯基、(C1-C6)-烷基亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷基磺醯基、(C1-C6)-鹵烷基磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷基磺醯基、(C1-C6)-烷基磺醯基-(C1-C6)-烷基、(C1-C6)-烷基磺醯氧基、(C1-C6)-烷基羰基、(C1-C6)-烷基羰基-(C1-C6)-烷基、(C1-C6)-烷基硫基羰基、(C1-C6)-鹵烷基羰基、(C1-C6)-烷基羰氧基、(C1-C6)-烷氧基羰基、(C1-C6)-鹵烷氧基羰基、胺基羰基、(C1-C6)-烷基胺基羰基、(C1-C6)-烷基胺基硫基羰基、二-(C1-C6)-烷基胺 基羰基、二-(C1-C6)-烷基胺基硫基羰基、(C2-C6)-烯基胺基羰基、二-(C2-C6)-烯基胺基羰基、(C3-C8)-環烷基胺基羰基、(C1-C6)-烷基磺醯基胺基、(C1-C6)-烷基胺基、二-(C1-C6)-烷基胺基、胺基磺醯基、(C1-C6)-烷基胺基磺醯基、二-(C1-C6)-烷基胺基磺醯基、(C1-C6)-烷基亞碸醯亞胺基、胺基硫基羰基、(C1-C6)-烷基胺基硫基羰基、二-(C1-C6)-烷基胺基硫基羰基、(C3-C8)-環烷基胺基、NHCO-(C1-C6)-烷基((C1-C6)-烷基羰基胺基),或其中該取代基彼此獨立可被選自苯基及5-或6-員雜芳環,其中苯基及該環可選擇地經選自下列所組成群組之相同或不同之取代基單取代-或多取代:C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-環烷基、C1-C6-鹵烷基、C2-C6-鹵烯基、C2-C6-鹵炔基、C3-C6-鹵環烷基、鹵素、CN、NO2、C1-C4-烷氧基、C1-C4-鹵烷氧基,及n 代表0、1或2。
式(I)化合物,其中較佳地 在代表單鍵及雙鍵之情況,且Aa至Ae因此形成芳香環, Aa 代表氮或碳,Ab 代表氮、氧、硫或C(R11),Ac 代表氮、氧、硫或C(R12),Ad 代表氮、氧、硫或C(R13),Ae 代表氮或碳, 其中基團Aa、Ab、Ac、Ad及Ae中至多三個可代表氮,且至多一個可代表氧或至多一個可代表硫, 或,在僅代表單鍵, Aa 代表碳,Ab 代表硫、氧或C(R11)(R15),Ac 代表硫、氧或C(R12)(R16)且Ad 代表硫、氧或C(R13)(R17),Ae 代表碳,其中基團Aa、Ab、Ac、Ad及Ae中至多一個可至多一個代表氧或硫,R1 較佳地代表(C1-C4)-烷基、(C1-C4)-羥基烷基、(C1-C4)-鹵烷基、(C2-C4)-烯基、(C2-C4)-鹵烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C3-C6)-環烷基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-鹵烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯基-(C1-C4)-烷基,或代表(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C3-C6)-環烷基,其各可選擇地經相同或不同芳基或雜環基取代基單取代或二取代,其中芳基或雜環基可在各情況中可選擇地經相同或不同之鹵素、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C3-C4)-環烷基、(C1-C4)-烷氧基或(C1-C4)-烷基硫基取代基單取代或二取代,R11、R12、R13、R15、R16、R17 彼此獨立較佳地代表氫、氰基、鹵素、硝基、羥基、胺基、三-(C1-C4)-烷基矽烷基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、 (C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-羥基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-鹵烯基、(C2-C4)-氰基烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C2-C4)-氰基炔基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、(C1-C4)-氰基烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、(C1-C4)-烷基羥基亞胺基、(C1-C4)-烷氧基亞胺基、(C1-C4)-烷基-(C1-C4)-烷氧基亞胺基、(C1-C4)-鹵烷基-(C1-C4)-烷氧基亞胺基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯氧基、(C1-C4)-烷基羰基、(C1-C4)-鹵烷基羰基、胺基羰基、胺基硫基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基磺醯基胺基、(C1-C4)-烷基胺基、二-(C1-C4)-烷基胺基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基、胺基硫基羰基、(C1-C4)-烷基羰基胺基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、(C1-C4)-烷基羰基-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CO-(C1-C6)-烷基)、((C1-C4)-烷氧基羰基)胺基(-NHCOO-(C1-C4)-烷基)、((C1-C4)-烷氧基羰基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-COO-(C1-C6)-烷基)、(C1-C4)-烷基胺甲醯氧基(-OCONH-(C1-C4)-烷基)、二-(C1-C4)-烷基胺甲醯氧基(-OCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)胺基 (-NHCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CON-(C1-C4)-二烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C4)-烷基胺基(-N(C1-C4)-烷基-CONH2)或較佳地代表苯基或5-或6-員雜芳基,其各可選擇地經相同或不同之取代基單取代-或雙取代,其中(在雜芳基之情況下)可選擇地存在至少一個羰基基團且該雜原子係選自N、S及O,且其中可能之取代基在各情況中如下:氰基、鹵素、乙醯基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C2-(C1-C4)-烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯氧基、(C1-C4)-烷基羰基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基磺醯基胺基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基或(C1-C4)-烷基羰基胺基,其中在基團R11、R12、R13、R15、R16、R17中僅一或二個代表氫以外的取代基,且,在R11及R15、R12及R16或R13及R17不代表氫,R15、R16及R17 各彼此獨立僅代表氰基、鹵素、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基或(C1-C4)-氰基烷基,Q 較佳地代表Q1至Q13及Q15至Q20所組成群組之雜芳族9-員或12-員稠合雙環或三環系統
其中R4 較佳地代表(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C1-C4)-羥基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-鹵烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-烯氧基-(C1-C4)-烷基、(C2-C4)-鹵烯氧基-(C1-C4)-烷基、(C2-C4)-鹵烯基、(C2-C4)-氰基烯基、(C2-C4)-炔基、(C2-C4)-炔氧基-(C1-C4)-烷基、(C2-C4)-鹵炔基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基硫基-(C1-C4)-烷基、(C1-C4)-烷基亞磺醯基-(C1-C4)-烷基、(C1-C4)-烷基磺醯基-(C1-C4)-烷基或(C1-C4)-烷基羰基-(C1-C4)-烷基,R5、R6 彼此獨立較佳地代表氫、氰基、鹵素、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C2-C4)-烯基、(C2-C4)-鹵烯基、(C2-C4)-炔基、(C2-C4)-鹵炔基、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、(C1-C4)-烷氧基亞胺基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯氧基、(C1-C4)-烷基羰基、(C1-C4)-鹵烷基羰基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基磺醯基胺基、(C1-C4)-烷基胺基、二-(C1-C4)-烷基胺基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基或二-(C1-C4)-烷基胺基磺醯基,及n 較佳地代表0、1或2。
式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物,
其中R1 特佳地代表(C1-C4)-烷基、(C1-C4)-鹵烷基或(C3-C6)-環烷基,R11、R12、R13、R15、R16、R17 彼此獨立特佳地代表氫、氰基、鹵素、硝基、羥基、(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基 磺醯基、(C1-C4)-鹵烷基磺醯基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、(C1-C4)-烷基羰基-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CO-(C1-C6)-烷基)、((C1-C4)-烷氧基羰基)胺基(-NHCOO-(C1-C4)-烷基)、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)胺基(-NHCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CON-(C1-C4)-二烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH2)或特佳地代表苯基、三唑或吡唑,其各可選擇地經相同或不同之取代基單取代-或雙取代,在各情況中可能的取代基為:氰基、鹵素、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C1-C4)-烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯氧基、(C1-C4)-烷基羰基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基磺醯基胺基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基、(C1-C4)-烷基羰基胺基, 其中基團R11、R12、R13、R15、R16、R17中僅一或二個代表氫以外的取代基,且,在R11及R15、R12及R16或R13及R17不代表氫之情況,R14、R15、R16及R17各彼此獨立僅代表氰基、鹵素、(C3-C6)-環烷基、(C3-C6)-環烷基-(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基或(C1-C4)-鹵烷基,Q 特佳地代表Q1、Q2、Q3、Q5、Q6、Q8、Q9、Q10、Q12、Q15及Q20所組成群組之雜芳族9-員稠合雙環環系統,
R4 特佳地代表(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,R5 特佳地代表鹵素、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基亞磺醯基或(C1-C4)-鹵烷基磺醯基,R6 特佳地代表氫、氰基、鹵素或(C1-C4)-烷基,且 n 特佳地代表0、1或2。
非常特佳為給予式(Ia)、(Ib)、(Id)、(Ie)、(Ii)至(Ik)及(In)至(It)化合物
其中R1 非常特佳地代表(C1-C4)-烷基、(C3-C6)-環烷基或(C1-C4)-鹵烷基,R11、R13、R15、R16、R17彼此獨立非常特佳地代表氫、鹵素、(C1-C4)-鹵烷基或(C1-C4)-烷基,R12 非常特佳地代表氫、氰基、鹵素、硝基、羥基、(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、 (C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基-胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、(C1-C4)-烷基羰基-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CO-(C1-C6)-烷基)、((C1-C4)-烷氧基羰基)胺基(-NHCOO-(C1-C4)-烷基)、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)胺基(-NHCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH-(C1-C4)-烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH2)或非常特佳地代表苯基、吡唑或三唑,其各可選擇地經相同或不同之取代基單取代-或雙取代,在各情況中可能的取代基為:氰基、鹵素、(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯氧基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基羰基胺基,其中基團R11、R12、R13、R15、R16、R17中僅一或二個代表氫以外的取代基,且在R11及R15、R12及R16或R13及R17不代表氫之情況,R14、R15、 R16及R17各彼此獨立僅代表鹵素、(C1-C4)-鹵烷基或(C1-C4)-烷基,Q 非常特佳地代表Q1、Q2、Q3、Q5、Q6、Q12、Q10、Q15及Q20所組成群組之雜芳族9-員稠合雙環環系統
其中R4 非常特佳地代表(C1-C4)-烷基,R5 非常特佳地代表鹵素、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基或(C1-C4)-鹵烷基硫基,R6 非常特佳地代表氫,及n 非常特佳地代表0、1或2。
重點在於提供式(Ia)、(Ib)、(Id)、(Ii)、(Ij)、(Ik)及(In)化合物,
其中R1 最佳地代表(C1-C4)-烷基,R13、R15、R16、R17 彼此獨立最佳地代表氫,R11 最佳地代表氫、(C1-C4)-烷基或鹵素,R12 最佳地代表氫、鹵素、(C1-C4)-烷基、環丙基、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基羰基胺基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、環丙基羰基胺基、(C1-C4)-烷基羰基-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CO-(C1-C6)-烷基)、((C1-C4)-烷氧基羰基)胺基(-NHCOO-(C1-C4)-烷基)、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH2)或代表苯基、吡唑或三唑,其各可選擇地經相同或不同之鹵素單取代或二取代,Q 最佳地代表Q2、Q3及Q15所組成群組之雜芳族9-員稠合雙環環系 統,
R4 最佳地代表(C1-C4)-烷基,R5 最佳地代表(C1-C4)-鹵烷基,R6 最佳地代表氫及n 最佳地代表0或2。
特佳為給予式(Ia)、(Id)、(In)化合物 ,其中 R1 尤其是代表乙基,R13、R15、R16、R17 尤其是代表氫,R12 尤其是代表氫或三氟甲基,R11 尤其是代表氫,Q 尤其是代表Q3,R4 尤其是代表甲基,R5 尤其是代表三氟甲基,R6 尤其是代表氫,及n 尤其是代表2。
下文中,關於式(I)化合物的陳述當然也適用於式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It),其被式(I)所包圍。
下文中所表達之組態x與其中代表1、2、3、4、5或6的組態x-1或組態x-2同義。
在較佳的具體實施例中,本發明係關於式(I)化合物,其中R1 代表(C1-C4)-烷基、(C1-C4)-鹵烷基或(C3-C6)-環烷基,且Aa、Ab、Ac、Ad、R4、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(5)或組態(6)中所述意義。
在特佳的具體實施例,本發明係關於式(I)化合物,其中R1 代表(C1-C4)-烷基,且Aa、Ab、Ac、Ad、R4、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(6)中所述意義。
在非常特佳的具體實施例,本發明係關於式(I)化合物,其中R1 代表乙基,且Aa、Ab、Ac、Ad、R4、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)中所述意義。
在較佳的具體實施例,本發明係關於式(I)化合物,其中Q 代表Q1至Q13及Q15至Q21所組成群組之雜芳族9-員或12-員稠合雙環或三環系統。
在特佳的具體實施例,本發明係關於式(I)化合物,其中Q 代表Q1、Q2、Q3、Q5、Q6、Q8、Q9、Q10、Q12、Q15、Q20及Q21所組成群組之雜芳族9-員或12-員稠合雙環或三環系統, 且Aa、Ab、Ac、Ad、R4、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、R1及n具有組態(1)或組態(2)或組態(4)或組態(5)或組態(6)中所述意義。
在非常特佳的具體實施例,本發明係關於式(I)化合物,其中Q 代表Q1、Q2、Q3、Q5、Q6、Q12、Q10、Q15、Q20及Q21所組成群組之雜芳族9-員或12-員稠合雙環或三環系統,且Aa、Ab、Ac、Ad、R4、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、R1及n具有組態(1)或組態(2)或組態(3)或組態(5)或組態(6)中所述意義。
在最佳的具體實施例,本發明係關於式(I)化合物,其中Q 代表Q2、Q3、Q15及Q21所組成群組之雜芳族9-員稠合雙環環系統,且Aa、Ab、Ac、Ad、R4、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、R1及n具有組態(1)或組態(2)或組態(3)或組態(4)中所述意義。
在較佳的具體實施例,本發明係關於式(I)化合物,其中R4 代表(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-氰基烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,且Aa、Ab、Ac、Ad、R1、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(4)或組態(5)或組態(6)中所述意義。
在特佳的具體實施例,本發明係關於式(I)化合物,其中R4 代表(C1-C4)-烷基,且Aa、Ab、Ac、Ad、R1、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(6)中所述意義。
在非常特佳的具體實施例,本發明係關於式(I)化合物,其中R4 代表甲基,且 Aa、Ab、Ac、Ad、R1、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)中所述意義。
在較佳的具體實施例,本發明係關於式(I)化合物,其中R5 代表鹵素、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-鹵烷基磺醯基或代表可選擇地經單氰基-取代之(C3-C6)-環烷基,且Aa、Ab、Ac、Ad、R1、R4、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(4)或組態(5)或組態(6)中所述意義。
在特佳的具體實施例,本發明係關於式(I)化合物,其中R5 代表鹵素、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-鹵烷基磺醯基或代表可選擇地經單氰基-取代之(C3-C6)-環烷基,且Aa、Ab、Ac、Ad、R1、R4、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(5)或組態(6)中所述意義。
在非常特佳的具體實施例,本發明係關於式(I)化合物,其中R5 代表(C1-C4)-鹵烷基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-鹵烷基亞磺醯基或經單氰基-取代之環丙基,且Aa、Ab、Ac、Ad、R1、R4、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(6)中所述意義。
在特佳的具體實施例,本發明係關於式(I)化合物,其中R5 代表(C1-C4)-鹵烷基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基磺醯基或(C1-C4)-鹵烷基亞磺醯基,且 Aa、Ab、Ac、Ad、R1、R4、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)或組態(6)中所述意義。
在更特佳的具體實施例,本發明係關於式(I)化合物,其中R5 代表三氟甲基磺醯基、三氟甲基亞磺醯基、三氟甲基硫基、三氟甲基或五氟乙基,且Aa、Ab、Ac、Ad、R1、R4、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)中所述意義。
在較佳的具體實施例,本發明係關於式(I)化合物,其中Q 代表Q2、Q3、Q15及Q21所組成群組之雜芳族9-員稠合雙環環系統,R4 代表甲基,R5 代表三氟甲基磺醯基、三氟甲基亞磺醯基、三氟甲基硫基、三氟甲基或五氟乙基,R6 代表氫,R7 代表甲基,及Aa、Ab、Ac、Ad、R1、R8、R11、R12、R13、R15、R16、R17及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)中所述意義。
尤其是較佳地,下列結構(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)產生式(I)
其中R1、R4、R5、R6、R7、R8、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(4)或組態(5)或組態(6)中所述意義。
尤其是較佳地,下列結構(Ia)、(Ib)、(Id)、(Ie)、(Ii)至(Ik)、(In)、(Iq)及(Ir)產生式(I)
其中R1、R4、R5、R6、R7、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(5)或組態(6)中所述意義。
尤其是特佳地,下列結構產生式(I)(Ia)、(Id)、(Ij)及(In),
其中R1、R4、R5、R6、R7、R11、R12、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)中所述意義。
在較佳的具體實施例,本發明係關於式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物,其中R13、R15、R16、R17 彼此獨立代表氫、鹵素、(C1-C4)-鹵烷基或(C1-C4)-烷基,R11、R12 彼此獨立代表氫、氰基、鹵素、硝基、羥基、(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-鹵烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、胺基磺醯基、(C1-C4)-烷基胺基磺醯基、二-(C1-C4)-烷基胺基磺醯基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、(C1-C4)-烷基羰基-(C1-C4)-烷基胺基 (-N-(C1-C4)-烷基-CO-(C1-C6)-烷基)、((C1-C4)-烷氧基羰基)胺基(-NHCOO-(C1-C4)-烷基)、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、(N,N-二-(C1-C4)-烷基胺甲醯基)胺基(-NHCON-(C1-C4)-二烷基)、(N-(C1-C4)-烷基胺甲醯基)-(C1-C4)-烷基胺基(-N-(C1-C4)-烷基-CONH-(C1-C4)-烷基)、胺甲醯基胺基(-NHCONH2)、(胺甲醯基)-N-(C1-C4)-烷基胺基(-N(C1-C4)-烷基-CONH2)或非常特佳地代表苯基、吡唑或三唑,其各可選擇地經相同或不同之取代基單取代-或雙取代,在各情況中可能的取代基為:氰基、鹵素、(C3-C6)-環烷基、(C1-C4)-烷基-(C3-C6)-環烷基、鹵-(C3-C6)-環烷基、(C1-C4)-烷基、(C1-C4)-鹵烷基、(C1-C4)-烷氧基、(C1-C4)-烷基硫基、(C1-C4)-鹵烷基硫基、(C1-C4)-烷基亞磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-烷基磺醯基、(C1-C4)-鹵烷基磺醯基、(C1-C4)-烷基磺醯氧基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C1-C4)-烷基羰基胺基,其中基團R11、R12、R13、R15、R16、R17至多二個代表氫以外的取代基,且,在R11及R15、R12及R16或R13及R17不代表氫之情況,R14、R15、R16及R17各彼此獨立僅代表鹵素、(C1-C4)-鹵烷基或(C1-C4)-烷基,或,在結構式(In)至(It)之情況,R11及R15或R13及R17在各情況中另一起非常特佳地代表氧(=O),且其中Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7、Q及n具有組態(1)或組態(2)或組態(3)或組態(5)或組態(6)中所述意義。
在特佳的具體實施例,本發明係關於式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物,其中R13 代表氫或鹵素,R15、R16、R17 代表氫,R11、R12 彼此獨立代表氫、羥基、氰基、鹵素、(C1-C4)-烷基、(C3-C6)-環烷基、(C1-C4)-鹵烷基、(C1-C4)-鹵烷氧基、胺基羰基、(C1-C4)-烷基胺基羰基、二-(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺基、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、苯基,或代表吡唑或三唑,其各可選擇地經(C1-C4)-烷基、鹵素或(C1-C4)-鹵烷基單取代,或,在結構式(In)至(It)之情況,R11及R15或R13及R17在各情況中另一起代表氧(=O),其中Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(6)中所述意義。
在非常特佳的具體實施例,本發明係關於式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物,其中R13 代表氫或鹵素,R15、R16、R17 代表氫,R11 代表氫、羥基、氰基、鹵素、(C1-C4)-烷基、(C3-C6)-環烷基、(C1-C4)-鹵烷基、胺基羰基、(C1-C4)-烷基胺基羰基、(C3-C6)-環烷基胺基羰基、(C1-C4)-烷基羰基胺基(-NHCO-(C1-C4)-烷基)、(C3-C6)-環烷基羰基胺 基、(N-(C1-C4)-烷基胺甲醯基)胺基(-NHCONH-(C1-C4)-烷基)、苯基,或代表吡唑或三唑,其各可選擇地經(C1-C4)-烷基、鹵素或(C1-C4)-鹵烷基單取代,R12 代表氫、鹵素、(C1-C4)-烷基、(C3-C6)-環烷基或(C1-C4)-鹵烷基,或,在結構式(In)至(It)之情況,R11及R15或R13及R17在各情況中另一起代表氧(=O),其中Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)或組態(6)中所述意義。
在同樣非常特佳的具體實施例,本發明係關於式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物,其中R13 代表氫或氟,R15、R16、R17 代表氫,R11 代表氫、羥基、氰基、環丙基、三氟甲基、溴、氟、碘、胺基羰基、甲基胺基羰基、甲基羰基胺基、環丙基羰基胺基、(N-甲基胺甲醯基)胺基(-NHCONHMe)、苯基、N-甲基吡唑、三氟甲基咪唑或氯吡唑,R12 代表氫、環丙基、甲基、三氟甲基或氯,或,在結構式(In)至(It)之情況,R11及R15或R13及R17在各情況中另一起代表氧(=O),其中Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)中所述意義。
在本發明較佳的具體實施例,在式(Ia)、(Ib)、(Id)、(Ie)、(Ig)、(Ih)、(Ij)或(Ik)化合物中,至少一個基團R11或R12代表不同於氫之基團。
較佳為另賦予式I(a)、I(d)及I(j)化合物,其中R11及/或R12代表根據組態(1)或組態(2)或組態(3)或組態(4)或組態(5)或組態(6)之基團,但並不代表氫,且其中R1、R4、R5、R6、R7、R11、R13、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)或組態(6)中所述意義。
較佳為另賦予式I(a)化合物
其中R1、R4、R5、R6、R7、R11、R12、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)或組態(6)中所述意義。
特佳為給予式I(a)化合物 ,其中 R1 代表(C1-C4)-烷基,R12 代表氫、(C1-C4)-烷基、鹵素、(C3-C6)-環烷基或(C1-C4)-鹵烷基、R11 代表氫、氰基、(C3-C6)-環烷基、(C1-C4)-鹵烷基、鹵素、胺基羰基、(C1-C4)-烷基胺基羰基、(C1-C4)-烷基羰基胺基、(C3-C6)-環烷基羰基胺基、(N-(C1-C4)-烷基胺甲醯基)、苯基、N-(C1-C4)-烷基吡唑、(C1-C4)-鹵烷基咪唑或鹵吡唑,Q 代表Q3、Q15或Q21,R4 代表(C1-C4)-烷基, R5 代表(C1-C4)-鹵烷基磺醯基、(C1-C4)-鹵烷基亞磺醯基、(C1-C4)-鹵烷基硫基、(C1-C4)-鹵烷基或經單氰基-取代之環丙基,R6 代表氫,R7 代表(C1-C4)-烷基、環丙基、甲氧基甲基或甲氧基乙基,且n 代表2。
非常特佳為給予式I(a)化合物 ,其中 R1 代表乙基,R12 代表氫、甲基、氯、環丙基或三氟甲基,R11 代表氫、氰基、環丙基、三氟甲基、溴、碘、胺基羰基、甲基胺基羰基、甲基羰基胺基、環丙基羰基胺基、(N-甲基胺甲醯基)胺基(-NHCONHMe)、苯基、N-甲基吡唑、三氟甲基咪唑或氯吡唑,Q 代表Q3、Q15或Q21,R4 代表甲基,R5 代表三氟甲基磺醯基、三氟甲基亞磺醯基、三氟甲基硫基、三氟甲基或五氟乙基,R6 代表氫,R7 代表甲基,及 n 代表2。
較佳為另賦予式I(d)化合物
其中R1、R4、R5、R6、R11、R12、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)或組態(6)中所述意義。
特佳為另賦予I(d)化合物 ,其中 R1 代表(C1-C4)-烷基,R12 代表氫或(C1-C4)-鹵烷基、較佳地(C1-C4)-鹵烷基,R11 代表氫,Q 代表Q3,R4 代表(C1-C4)-烷基,R5 代表(C1-C4)-鹵烷基,R6 代表氫,且n 代表2。
非常特佳為另賦予式I(d)化合物 ,其中 R1 代表乙基,R12 代表氫或三氟甲基,較佳地三氟甲基,R11 代表氫,Q 代表Q3,R4 代表甲基,R5 代表三氟甲基,R6 代表氫,且n 代表2。
較佳為另賦予式I(j)化合物
其中R1、R4、R5、R6、R12、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)或組態(6)中所述意義。
特佳為另賦予式I(j)化合物 ,其中 R1 代表(C1-C4)-烷基,R12 代表氫或(C1-C4)-鹵烷基,較佳地(C1-C4)-鹵烷基,Q 代表Q2、Q3或Q15,R4 代表(C1-C4)-烷基,R5 代表(C1-C4)-鹵烷基,R6‧‧‧代表氫,且n 代表2。
非常特佳為另賦予式I(j)化合物 ,其中 R1 代表乙基、R12 代表氫或三氟甲基,較佳地三氟甲基、Q 代表Q2,Q3或Q15、R4 代表甲基、R5 代表三氟甲基或五氟乙基、R6 代表氫,且n 代表2。
較佳為另賦予式I(n)化合物
其中R1、R4、R5、R6、R11、R12、R12、R15、R16、R17、Q及n具有組態(1)或組態(2)或組態(3)或組態(4)或組態(5)或組態(6)中所述意義。
特佳為另賦予式I(n)化合物 ,其中 R1 代表(C1-C4)-烷基,R12、R15、R16、R17 代表氫,R11、R13 彼此獨立代表氫、羥基或鹵素,或R11及R15或R13及R17在各情況中一起代表=O,Q 代表Q3,R4 代表(C1-C4)-烷基,R5 代表(C1-C4)-鹵烷基,R6 代表氫,及n 代表2。
非常特佳為另賦予式I(n)化合物 ,其中 R1 代表乙基,R12、R15、R16、R17 代表氫,R11、R13 彼此獨立代表氫、羥基或氟, 或R11及R15或R13及R17在各情況中一起代表=O。Q 代表Q3,R4 代表甲基,R5 代表三氟甲基,R6 代表氫,及n 代表2。
除非另有陳述,依定義,鹵素選自氟、氯、溴與碘之群組,繼而較佳選自氟、氯與溴之群組。
本案發明上下文中,除非另有不同定義,術語「烷基」,其本身或進一步與其他用語組合,例如鹵烷基,被理解是表示具1至12個碳原子且可為分支或未分支之飽和、脂族烴之基團。C1-C12-烷基基團之例子為甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、異戊基、新戊基、第三戊基、1-甲基丁基、2-甲基丁基、1-乙基丙基、1,2-二甲基丙基、己基、正庚基、正辛基、正壬基、正癸基、正十一基及正十二基。
根據本發明,除非另有不同定義,術語「烯基」,其本身或進一步與其他用語組合,被理解為表示具有至少一個雙鍵之直鏈或分支之C2-C12-烯基基團,例如乙烯基、烯丙基、1-丙烯基、異丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1,3-丁二烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1,3-戊二烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基及1,4-己二烯基。
根據本發明,除非另有不同定義,術語「炔基」,其本身或進一步與其 他用語組合,被理解為表示具有至少一個三鍵之直鏈或分支C2-C12-炔基基團,例如乙炔基、1-丙炔基及丙炔基。炔基基團亦可含有至少一個雙鍵。
根據本發明,除非另有不同定義,術語「環烷基」,其本身或進一步與其他用語組合,被理解為表示C3-C8-環烷基基團,例如環丙基、環丁基、環戊基、環己基、環庚基及環辛基。
術語「烷氧基」,其本身或進一步與其他用語(例如鹵烷氧基)組合,在本案中被理解為表示O-烷基基團,其中「烷基」用語定義如上。
經鹵素-取代之基團,例如鹵烷基,係經單-或多鹵化,至多達可能之取代基的最多數目。在多鹵化的情況,該鹵素原子可相同或不同。除非另有陳述,可選擇地經取代之基團可被單取代-或多取代,其中在多取代之情況該取代基可相同或不同。
根據本發明,除非另有不同定義,術語「芳基」被理解為表示具有6至14個碳原子之芳族基團,較佳為苯基、萘基、蒽基或菲基,更佳為苯基。
除非另有不同定義,「芳烷基」被理解為表示根據本發明定義之基團「芳基」與「烷基」的組合,其中基團通常經由烷基鍵結,其例子為苄基、苯乙基或α-甲苄基,特佳為苄基。
除非另有不同定義,「雜芳基」或「雜芳環」表示單-、雙-或三環雜環基,其由碳原子與至少一個雜原子組成,其中至少一環為芳族。較佳地,雜芳基含有3、4、5、6、7或8個碳原子,且其選自下列所組成之群組:呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、唑基、異唑基、噻唑基、異噻唑基、1,2,3-二唑基、1,2,4-二唑基、1,3,4-二唑基、1,2,5-二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、嗒基、吡基、1,2,3-三基、1,2,4-三基、1,3,5-三基、苯并呋喃基、苯并異呋喃基、苯并噻吩基、苯并異噻吩基、吲哚基、異吲哚基、吲唑基、苯并噻唑基、苯并異噻唑基、 苯并唑基、苯并異唑基、苯并咪唑基、2,1,3-苯并二唑、喹啉基、異喹啉基、啉基、呔基、喹唑啉基、喹啉基、啶基、苯并三基、嘌呤基、喋啶基、咪唑并吡啶基及吲基(indolizinyl)。
除非另有不同定義,「雜環基」表示環中碳原子及至少一個雜原子的單環、飽和或部分飽和的4-、5-、6-或7-員環。較佳地,該雜環基含3、4、5或6個碳原子及1或2個氧、硫及氮所組成群組之雜原子。雜環基之實例為氮雜環丁烷基、偶氮烷基,吖基、氧雜環丁烷基、氧雜環戊烷基、烷基、二烷基、硫雜環丁基、硫代丙醯基、噻烷基和四氫呋喃基。
依據取代基之性質,式(I)的化合物可以在不同組成物中採用幾何及/或光學異構物或對應的異構物混合物形式。這些立體異構物可為例如對映異構物、非對映異構物、阻轉異構物或幾何異構物。因此本發明包括純立體異構物和這些異構體的任何所欲混合物。
式(I)化合物亦可以以鹽類存在,特別是酸加成鹽類和金屬鹽錯合物。式(I)化合物及其酸加成鹽類和金屬鹽錯合物具有良好的功效,尤其是用於防治動物害蟲。
通式(I)化合物的適當的鹽類包括常規的無毒鹽類,即鹽類與適當的鹼和鹽類與加成酸。
較佳為給予具無機鹼類之鹽類,例如鹼金屬鹽類,例如鈉、鉀或銫鹽類,鹼土金屬鹽類,例如鈣或鎂鹽類,銨鹽類,具有機鹼類及具無機胺類之鹽類,例如三乙基銨、二環己基銨、N,N'-二苄基伸乙二銨、吡錠、甲基吡錠或乙醇銨鹽類、具無機酸類之鹽類,例如鹽酸鹽、氫溴酸鹽、二氫硫酸鹽、三氫硫酸鹽或磷酸鹽,具有機羧酸或有機磺酸類之鹽類,例如甲酸鹽、乙酸鹽、三氟乙酸鹽、馬來酸鹽、酒石酸鹽、甲烷磺酸鹽、苯磺酸鹽或對甲苯磺酸鹽,具鹼性胺基酸之鹽類,例如精胺酸、天冬胺酸或谷胺酸,等等。
上述一般術語或在較佳範圍內列出的基團定義或說明對應地適用於最 終產物及起始材料和中間產物。這些基團定義可以根據需要相互組合,即包括各較佳範圍之間的組合。
本發明較佳係使用式(I)的化合物,其含有上述所列之較佳含義的組合。
本發明特佳係使用式(I)的化合物,其含有上述所列之特佳含義的組合。
本發明非常特佳係使用式(I)的化合物,其含有上述所列之非常特佳含義的組合。
本發明最佳係使用式(I)的化合物,其含有上述所列之最佳含義的組合。
本發明尤其被使用者係式(I)化合物,其含有上述所列特別被重視之含義的組合。
可根據下列流程圖中所示方法獲得本發明式(I)化合物:
基團Aa、Ab、Ac、Ad、Ae具有上述之定義,X代表鹵素。
式(IV)化合物可商業上獲得或通常可由巰基乙酸(II)衍生物與式(III)醛類製備。適用於反應的溶劑例如,極性溶劑,例如DMF或二甲亞碸,或醇類,例如甲醇或乙醇。反應可藉由添加鹼來加速,例如胺鹼,例如三乙胺,或無機鹼類,例如,碳酸鉀或甲醇鈉,或以其他添加劑加速,例如18-冠-6或銅鹽類。
在Aa代表碳、Ab代表C(R11)、Ac代表C(R12)、Ad代表硫、Ae代表碳之情況,以例如,類似於WO2008/106019 A2,2008進行製備。
在Aa代表碳、Ab代表硫、Ac代表C(R12)、Ad代表C(R13)、Ae代表 碳之情況,以例如,類似於Journal of Medicinal Chemistry,1991,vol.34,1805-1818進行製備。
在代表碳、Ab代表C(R11)、Ac代表硫、Ad代表C(R13)、Ae代表碳之情況,以例如,類似於Chemistry-A European Journal,2016,vol.22,694-703進行製備。
在Aa代表碳、Ab代表C(R11)、Ac代表C(R12)、Ad代表氧、Ae代表碳之情況,以例如,類似於Collection of Czechoslovak Chemical Communications,1997,vol.62,1468-1480進行製備。
在Aa代表碳、Ab代表氧、Ac代表C(R12)、Ad代表C(R13)、Ae代表碳之情況,以例如,類似於US2003/236263 A1,2003進行製備。
在Aa代表碳、Ab代表氮、Ac代表C(R12)、Ad代表硫、Ae代表碳之情況,以例如,類似於US2014/200215 A1,2014或WO2015/193506 A1,2015進行製備。
在Aa代表碳、Ab代表氮、Ac代表硫、Ad代表氮、Ae代表碳之情況,以例如,類似於Journal of Medicinal Chemistry,1998,vol.41,109-116進行製備。
在Aa代表碳、Ab代表硫、Ac代表氮、Ad代表C(R13)、Ae代表碳之情況,以例如,類似於Australian Journal of Chemistry,1982,vol.35,393-404進行製備。
在Aa代表碳、Ab代表氮、Ac代表C(R12)、Ad代表氮、Ae代表碳之情況,以例如,類似於WO2011/119870 A1,2011進行製備。
在僅代表單鍵且Aa代表碳、Ab代表硫、氧或C(R11)(R15)、Ac代 表硫、氧或C(R12)(R16)及Ad代表硫、氧或C(R13)(R17)、Ae代表碳之情況,以例如,類似於Synthesis,1992,526-528進行製備。
在Aa代表碳、Ab代表C(R11)、Ac代表氮、Ad代表硫、Ae代表碳之情況,以例如如Arkivoc,2013,# 3 p.245-265中完整所述之五個步驟進行製備
二溴噻吩(V)以例如正丁基鋰之適當的鹼去質子化,然後以例如二甲基硫之硫親核試劑清除。
噻吩(VIII)的羰基化是在佛瑞德-克來福特(Friedel-Crafts)條件下藉由與醯基氯(VII)和例如三氯化鋁之強路易士酸(Lewis acid)反應而進行的。或者,此反應亦可先以N-溴代琥珀醯亞胺將噻吩(V)溴化然後加入鋰鹼的兩步驟進行。在轉移之後,鋰化的中間體可以例如醯氯(VII)之適當親核試劑清除,得到化合物(VIII)。
酮或醛(VIII)可在標準條件下轉化為肟(IX),此反應的適當反應條件為,例如,在例如甲醇之醇溶劑中加入羥基胺和乙酸鈉。
噻吩并噻唑(X)的分子內環化反應的進行是在肟的羥基官能化轉化為良好的離去基後,藉由在例如三乙胺之胺鹼存在與甲磺醯氯反應。
轉化為酸(XI)可藉由噻吩并異噻唑(X)與LDA的去質子化作用及以CO2之清除作用。
在Aa代表碳、Ab代表C(R11)、Ac代表氮、Ad代表C(R13)、Ae代表氮之情況,以例如,類似於EP1908766 A1,2008,藉由在氧氯化磷(步驟1)存在下環化(XII)而製備所需之前驅物(XIII)。
或者(步驟2),該反應亦可以類似於WO2011/37780 A1,2011,藉由將咪唑(XV)與β-羰基酯(XIV)反應而進行。
以下藉由實例方式描述製備式(XVII)化合物的一般方法,X代表鹵素,例如氟、氯、溴或碘。
直接轉化(IV)為硫化物(XVI)可藉由使用適當鹼進行定向鄰位鋰化,然後使用適當的二硫化物(XV)清除鋰化物質。用於此反應類型之特別適當的鹼為例如,2,2,6,6-四甲基哌啶-1-基鋰或第二丁基鋰與N,N,N',N'-四甲基-1,2-二胺基乙烷之組合。此反應類型敘述於例如Organic Letters,2006,vol.8,# 4 p.765-768之一般方法中或US2010/48531 A1,2010。
或者,轉化成硫化物(XVI)可由(IV)開始分二步驟進行。為此,最初在適當的鹵化劑存在下於標準條件下將化合物(IV)鹵化而得到(XVIII)。適當的鹵化劑為例如,N-溴琥珀醯亞胺(詳見例如Molecules,2016,1227)或N-氯琥珀醯亞胺。
然後式(XVI)化合物可藉由將式(XXVIII)化合物與式(XXIV)化合物在鹼存在下反應而製備。
例如甲基硫醇、乙基硫醇或異丙基硫醇之式(XXIV)硫醇衍生物為可商業上獲得或可藉由已知方法製備,例如類似於方法US2006/25633、US2006/111591、US2820062、Chemical Communications,13(2000),1163-1164或Journal of the American Chemical Society,44(1922),p.1329中所述方法。
轉化成式(XVI)化合物可進行淨反應或在溶劑中進行,較佳為選自在主要反應條件下為惰性之慣用溶劑中進行反應。較佳為給予醚類,例如二異丙基醚、二烷、四氫呋喃、1,2-二甲氧基乙烷、第三丁基甲基醚;腈類,例如乙腈或丙腈;芳香族烴類,例如甲苯或二甲苯;非質子極性溶劑,例如N,N-二甲基甲醯胺、N-甲基吡咯烷酮或二甲亞碸。
適當的鹼之實例為鹼金屬或鹼土金屬的乙酸鹽、磷酸鹽和碳酸鹽所組成群組之無機鹼類。本文中較佳給予碳酸銫、碳酸鈉及碳酸鉀,更適當的鹼為鹼金屬氫化物,例如氫化鈉。
該反應可在減壓下、標準壓力或高壓下處理,並於溫度0℃至200℃。
其中n代表2之式(XVII)化合物亦可在一階段製程終至被,其藉由氧化式(XVI)化合物。該氧化作用一般於溶劑中進行,較佳為給予鹵化烴類,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇類,例如甲醇或乙醇;甲酸、乙酸、丙酸或水.
適當氧化劑之實例為過氧化氫及間氯過苯甲酸。
該反應可在減壓下、標準壓力或高壓下處理,並於溫度-20℃至120℃。
用於製備其中Q代表Q1、Q2、Q3、Q4、Q5、Q6、Q7、Q8、Q9、Q15、Q20或Q21之式(I)化合物之一般方法以實例之方式並參照其中Q代表Q2之式(I)化合物於下文中敘述。在Q1、Q2、Q3、Q15、Q20及Q21之情況,Y代表-NHR4。在Q4及Q5之情況,Y代表氯,或在Q7及Q8之情況,Y代表SH。
式(I)化合物可以類似於US5576335中所述方法製備,其藉由在縮合劑或鹼存在下,將式(XIX)化合物與式(XVII)羧酸反應。
式(XIX)化合物為可商業上獲得或可藉由已知方法製備,例如類似於US2003/69257、WO2006/65703、WO2009/131237、WO2010/125985、WO2011/043404、WO2011/040629、WO2012/086848、WO2013/018928或WO2015/000715中所述之方法。
式(XVII)羧酸為可商業上獲得或可藉由已知方法製備,可能之製備途徑敘述於方法A、B、C及D。
該式(XIX)化合物與式(XVII)羧酸之反應可進行淨反應或在溶劑中進行,較佳為選自在主要反應條件下為惰性之慣用溶劑中進行反應。較佳為給予醚類,例如二異丙基醚、二烷、四氫呋喃、1,2-二甲氧基乙烷;鹵化烴類,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;腈類,例如乙腈或丙腈;芳香族烴類,例如甲苯或二甲苯;非質子極性溶劑,例如N,N-二甲基甲醯胺或N-甲基吡咯烷酮,或氮化合物,例如吡啶。
適當的縮合劑為例如,碳化二亞胺類,例如1-(3-二甲基胺基丙基)-3-乙基碳化二亞胺鹽酸鹽(EDCI)或1,3-二環己基碳化二亞胺。
適當的鹼為通常用於此類反應之無機鹼類,較佳為給予使用選自例示之鹼金屬或鹼土金屬之乙酸鹽、磷酸鹽、碳酸鹽和碳酸氫鹽所組成群組的鹼類。本文特佳為給予乙酸鈉、磷酸鈉、磷酸鉀、碳酸銫、碳酸鈉、碳酸鉀、碳酸氫鈉、碳酸氫鉀。
該反應可在減壓下、標準壓力或高壓下並於溫度0℃至180℃下達成;且較佳為,該反應進行於標準壓力及溫度20至140℃。
關於該酸(XVII)與縮合劑之反應的另一方案,該酸之轉化可藉由與草醯氯或磷醯氯反應成對應之醯氯然後與(XIX)反應。
用於製備其中Q代表Q10、Q11、Q12或Q13之式(I)化合物的一般方法以實例方式敘述於下文並參照其中Q為Q12之式(I)化合物。
在O,N-二甲基羥基胺鹽酸鹽之存在下,類似於WO2015/107117,WO2011/75643或EP2671582中所述方法,將式(XVII)羧酸轉化成式(XX)溫勒伯(Weinreb)醯胺。
式(XVII)羧酸為可商業上獲得或可藉由已知方法製備,可能的製備路徑敘述於方法A、B、C及D。
然後式(XX)化合物可藉由已知方法轉化,例如類似於WO2011/75643中所述方法,其使用格里納試劑(Grignard reagent)例如,如溴化甲基鎂至式(XXI)之酮。式(XXII)化合物可例如US2012/302573中所述已知方法,藉由後述鹵化作用而獲得。
式(I)化合物可藉由以式(XXIII)之胺類環化式(XXII)化合物而製備,該環化可例如在乙醇、乙腈或N,N-二甲基甲醯胺中根據已知方法進行,類似於例如根據WO2005/66177、WO2012/88411、WO2013/3298、US2009/203705、 US2012/258951、WO2012/168733、WO2014/187762或J.Med.Chem.31(1988)1590-1595中所述方法。
該式(XXIII)化合物為商業上可獲得。
用於製備其中Q代表Q1、Q2、Q3、Q4、Q5、Q6、Q7、Q8、Q9、Q15、Q20或Q21之式(I)化合物之一般方法藉由實例之方式及參照其中Q代表Q2之式(I)化合物敘述於下文中。在Q1、Q2、Q3、Q15、Q20及Q21之情況,Y代表-NHR4,在Q4及Q5之情況,Y代表氯,或在Q7及Q8之情況,Y代表SH。
可較佳地藉由使用適當鹼選擇性金屬化起始原料(IV),然後與鹵化劑反應而製備式XVIII化合物。
適當的鹼特別是氯化2,2,6,6-四甲基哌啶基鎂/氯化鋰複合物,如Chem.Eur.J.2011,17,866-872中所述。原則上,具有其它例如鋅或鋰之抗衡離子的其它立體受阻胺鹼,例如二異丙基二乙胺,也適用於該反應。再者,原 則上適當的為烷基鋰鹼,例如正丁基鋰。在這方面,詳見例如,WO 2005/12311 A1,2005。
適當的鹵化劑為例如,碘、溴、N-溴琥珀醯亞胺、N-碘琥珀醯亞胺及其他。
該轉化可進行淨反應或在溶劑中進行,較佳為選自在主要反應條件下為惰性之慣用溶劑中進行反應。較佳為給予醚類,例如二乙基醚、二異丙基醚、二烷、四氫呋喃、1,2-二甲氧基乙烷;芳香族烴類,例如甲苯或二甲苯。
該反應可在減壓下、標準壓力或高壓下並於溫度-78至100℃進行;該反應較佳在標準壓力及溫度-78℃至60℃達成。
上述方法的替代方案,式(XVII)化合物亦可藉由直接與例如,如溴或N-溴琥珀醯亞胺之鹵化劑反應而轉化成(XVIII)。
式(XXIV)化合物可以類似於US5576335中所述方法製備,其藉由將式(XIX)化合物與羧酸式(XVIII)於縮合劑或鹼存在下反應。
式(XIX)化合物為可商業上獲得或可藉由已知方法製備,例如類似於US2003/69257、WO2006/65703、WO2009/131237、WO2010/125985、WO2011/043404、WO2011/040629、WO2012/086848、WO2013/018928或WO2015/000715所述方法。
式(XVIII)羧酸為可商業上獲得或可藉由已知方法製備,可能的製備路徑敘述於方法A、B、C及D。
該式(XIX)化合物與式(XVIII)羧酸之反應可進行淨反應或在溶劑中進行,較佳為選自在主要反應條件下為惰性之慣用溶劑中進行反應。較佳為給予醚類,例如二異丙基醚、二烷、四氫呋喃、1,2-二甲氧基乙烷;鹵化烴類,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;腈類,例如乙腈或丙腈;芳香族烴類,例如甲苯或二甲苯;非質子極性溶劑,例如N,N- 二甲基甲醯胺或N-甲基吡咯烷酮,或氮化合物,例如吡啶。
適當的縮合劑例如為碳化二亞胺類,例如1-(3-二甲基胺基丙基)-3-乙基碳化二亞胺鹽酸鹽(EDCI)或1,3-二環己基碳化二亞胺。作為酸(XVIII)與縮合劑反應的替代方案,該酸可藉由與草醯氯或磷醯氯反應而轉化成對應之醯氯,然後與(XIX)反應。
適當的鹼為通常被使用於此類反應的無機鹼類。較佳為給予使用選自下列所例示組成群組之鹼:鹼金屬或鹼土金屬之乙酸鹽、磷酸鹽、碳酸鹽和碳酸氫鹽。本文特佳為給予乙酸鈉、磷酸鈉、磷酸鉀、碳酸銫、碳酸鈉、碳酸鉀、碳酸氫鈉、碳酸氫鉀。
該反應可在減壓下、標準壓力或高壓下及溫度0℃至180℃進行;且較佳,該反應進行於標準壓力及溫度20至140℃。
其中n=0之式(I)化合物可藉由偶合(XXIV)與適當硫醇(XXIV)而製備。可使用由金屬鹽或金屬複合物組成的催化劑及可選擇地適當的配位體進行偶合,可選擇地並添加鹼。
金屬鹽類、金屬錯合物及配位體之適當組合為例如,三-(二亞苄基丙酮)二鈀(0)、(5-二苯基苯醯基-9,9-二甲基-4-基)二苯基磷烷(詳見US2009/156642 A1)或碘化銅(詳見Australian Journal of Chemistry,1985,vol.38,899)。
可進行淨反應或在溶劑中進行,較佳為選自在主要反應條件下為惰性之慣用溶劑中進行反應。較佳為給予醚類,例如二異丙基醚、二烷、四氫呋喃、1,2-二甲氧基乙烷;鹵化烴類,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;腈類,例如乙腈或丙腈;芳香族烴類,例如甲苯或二甲苯;非質子極性溶劑,例如N,N-二甲基甲醯胺或N-甲基吡咯烷酮,或氮化合物,例如吡啶。
適當的鹼為通常被使用於此類反應的無機鹼類。較佳為給予使用選自 下列所例示組成群組之鹼:鹼金屬或鹼土金屬之乙酸鹽、磷酸鹽、碳酸鹽和碳酸氫鹽。
其中n為1或2之式(I)化合物可藉由氧化其中n=0之式(I)化合物而製備。該氧化作用一般進行於溶劑中,較佳為給予鹵化烴類,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇類,例如甲醇或乙醇;甲酸、乙酸、丙酸或水。
適當氧化劑之實例為過氧化氫及間氯過苯甲酸。
該反應在減壓下、標準壓力或高壓下及於溫度-20℃至120℃進行。
其中R11、R15、R13及R17可代表H、OH或F之式(In)化合物及其中R11及R15或R13及R17可一起代表羰基基團之化合物皆可獲自其中R11、R15、R13及R17=H之式(I)化合物,其藉由與適當的氟化劑和氧化劑反應。
適當的氟化劑為例如,Selectfluor、NFPy、Accufluor、NFSI,如Chem.Rev.2015,115,9073中所述。適當的氧化劑為過氧二硫酸鉀。金屬-催化法及光催化法同樣可行,且敘述於例如,Chem.Rev.2015,115,9073。
本發明亦關於控制動物害蟲之方法,其中容許式(I)化合物在動物害蟲 及/或彼之棲息處上起作用。動物害蟲的控制較佳地在農業和森林中,及在原料保護中進行。較佳地排除此方法為用於人體或動物體的手術性或治療性處理之方法及在人體或動物體上進行之診斷方法。
本發明進一步關於式(I)化合物作為殺蟲劑,尤其作為作物保護組成物之用途。
在本發明的上下文中,術語「殺蟲劑」在各情況中亦總是包含術語「植物保護組成物」。
給出良好的植物耐受性、有益的溫血動物毒性及良好的環境相容性之式(I)化合物適合於保護植物及植物組織對抗生物和非生物應力因素,以增加收成產率、改進收成原料的品質且控制動物害蟲,尤其為農業、園藝、畜牧業、水產培養、森林、花園和休閒設施、庫存產品與原料的保護,及衛生防區遇到的昆蟲、蜘蛛綱、蠕蟲,尤其為線蟲和軟體動物。
在本發明的上下文中,應瞭解術語「衛生」意指以預防疾病,尤其是傳染性疾病,且適合於保護人類及動物健康及/或保護環境及/或維持清潔為目標的任何及所有措施、防備及程式。根據本發明,這尤其包括用於例如紡織品或硬質表面(尤其為玻璃、木材、混凝土、瓷器、陶瓷、塑膠或亦為金屬的表面)之清潔、消毒及滅菌的措施,以確保該等無衛生害蟲及/或彼等糞便。關於此點,本發明的保護範圍較佳地排除欲應用於人體或動物體的手術性或治療性處理程式及在人體或動物體上進行之診斷程式。
術語「衛生防區」涵蓋其中該等衛生措施、防備及程式具有重要性的所有區域、技術領域和工業應用,例如關於在廚房、麵包房、機場、浴池、游泳池、商場、飯店、醫院、馬廄、動物飼養等中的衛生。
應瞭解術語「衛生害蟲」因此意指一或多種存在而使衛生防區有問題的動物害蟲,尤其是出於健康的理由。因此,主要的目標為避免或限制至最低的衛生害蟲出現於衛生防區中及/或暴露於衛生防區中的該等害蟲。這尤其可通過使用殺蟲劑而達成,可使用該等殺蟲劑同時防止侵襲及防止已 存在的侵襲。亦有可能使用防止或減少暴露於害蟲之調配物。衛生害蟲包括例如下文所述及之有機體。
術語「衛生保護」因此涵蓋用於維持及/或改進該等衛生措施、防備及程式的所有行動。
式(I)化合物較佳地可用作為殺蟲劑。彼等具有對抗一般敏感及抗藥性物種且亦對抗所有或特定的發育階段之活性。前述害蟲包括來自下列的害蟲:節肢動物門(Arthropoda),特別為來自蜘蛛綱(Arachnida),例如粉蟎屬(Acarus spp.),例如粗足粉蟎(Acarus siro)、枸杞瘤癭蟎(Aceria kuko)、桔瘤節蜱(Aceria sheldoni)、刺皮癭蟎屬(Aculops spp.)、刺癭蟎屬(Aculus spp.),例如桃銹蜱(Aculus fockeui)、蘋果銹蜱(Aculus schlechtendali)、花蜱屬(Amblyomma spp.)、橫紋葉蟎(Amphitetranychus viennensis)、銳緣蜱屬(Argas spp.)、牛蜱屬(Boophilus spp.)、紅鬚蟎屬(Brevipalpus spp.),例如紫偽葉蟎(Brevipalpus phoenicis)、苔蟎(Bryobia graminum)、苜蓿苔蟎(Bryobia praetiosa)、木蠍屬(Centruroides spp.)、恙蟎屬(Chorioptes spp.)、雞皮刺蟎(Dermanyssus gallinae)、歐洲塵蟎(Dermatophagoides pteronyssinus)、美洲塵蟎(Dermatophagoides farinae)、革蜱屬(Dermacentor spp.)、始葉蟎屬(Eotetranychus spp.),例如希克利始葉蟎(Eotetranychus hicoriae)、梨上癭蟎(Epitrimerus pyri)、真葉蟎屬(Eutetranychus spp.),例如斑氏真葉蟎(Eutetranychus banksi)、癭蟎屬(Eriophyes spp.),例如梨癭蟎(Eriophyes pyri)、傢具蟎(Glycyphagus domesticus)、足海鐮螯蟎(Halotydeus destructor)、半跗線蟎屬(Hemitarsonemus spp.),例如茶塵蟎((Hemitarsonemus latus)(=茶細蟎(Polyphagotarsonemus latus))、璃眼蜱屬(Hyalomma spp.)、硬蜱屬(Ixodes spp.)、球腹蛛屬(Latrodectus spp.)、絲蛛屬(Loxosceles spp.)、秋收恙蟎(Neutrombicula autumnalis),耐弗沙蟎屬(Nuphersa spp.)、小爪蟎屬(Oligonychus spp.),例如咖啡小爪蟎 (Oligonychus coffeae)、柏木小爪蟎(Oligonychus coniferarum)、冬青小爪蟎(Oligonychus ilicis)、甘蔗小爪蟎(Oligonychus indicus)、芒果小爪蟎(Oligonychus mangiferus)、草地小爪蟎(Oligonychus pratensis)、石榴小爪蟎(Oligonychus punicae)、樟小爪蟎(Oligonychus yothersi),鈍緣蜱屬(Ornithodoros spp.)、禽刺蟎屬(Ornithonyssus spp.)、紅蜘蛛屬(Panonychus spp.),例如桔爪蟎(Panonychus citri)(=Metatetranychus citri)),歐洲紅葉蟎(Panonychus ulmi)(=Metatetranychus ulmi))、橘銹蟎(Phyllocoptruta oleivora)、多迪吉蟎(Platytetranychus multidigituli)、茶細蟎(Polyphagotarsonemus latus),癢蟎屬(Psoroptes spp.)、扇頭蜱屬(Rhipicephalus spp.)、根蟎屬(Rhizoglyphus spp.)、疥蟎屬(Sarcoptes spp.)、中東金蠍(Scorpio maurus)、細蟎屬(Steneotarsonemus spp.)、稻細蟎(Steneotarsonemus spinki)、跗線蟎屬(Tarsonemus spp.),例如亂跗線蟎(Tarsonemus confusus)、白線蟎屬(Tarsonemus pallidus)、葉蟎屬(Tetranychus spp.),例如加拿大葉蟎(Tetranychus canadensis)、赤葉蟎(Tetranychus cinnabarinus)、土耳其斯坦葉蟎(Tetranychus turkestani)、紅蜘蛛葉蟎(Tetranychus urticae)、阿氏真恙蟎(Trombicula alfreddugesi),蠍屬(Vaejovis spp.)、輻蟎(Vasates lycopersici);來自唇足綱(Chilopoda),例如地蜈蚣屬(Geophilus spp.)、蚰蜒屬(Scutigera spp.);來自彈尾目或綱(Collembola),例如棘跳蟲(Onychiurus armatus)、綠圓跳蟲(Sminthurus viridis);來自雙足綱(Diplopoda),例如具斑馬陸(Blaniulus guttulatus);來自昆蟲綱,例如來自例如蜚蠊目(Blattodea),例如東方蜚蠊(Blatta orientalis)、亞洲蜚蠊(Blattella asahinai)、德國小蠊(Blattella germanica)、馬得拉蜚蠊(Leucophaea maderae)、歐洲缺翅姬蜚蠊(Loboptera decipiens)、斑蠊(Neostylopyga rhombifolia),綠蠊屬(Panchlora spp.)、木蠊 屬(Parcoblatta spp.)、大蠊屬(Periplaneta spp.),例如美洲大蠊(Periplaneta americana)、澳洲大蠊(Periplaneta australasiae)、蘇利南潛蠊(Pycnoscelus surinamensis)、棕帶蜚蠊(Supella longipalpa);來自鞘翅目(Coleoptera),例如鑲邊黃瓜甲蟲(Acalymma vittatum)、大豆象(Acanthoscelides obtectus),麗金龜屬(Adoretus spp.)、小蜂窩甲蟲(Aethina tumida)、楊毛臀螢葉甲(Agelastica alni)、瘦吉丁蟲(Agrilus spp.),例如光蠟瘦吉丁蟲(Agrilus planipennis)、纏皮瘦吉丁蟲(Agrilus coxalis)、栗雙線瘦吉丁蟲(Agrilus bilineatus)、樺銅瘦吉丁蟲(Agrilus anxius),叩甲屬(Agriotes spp.),例如直條叩頭蟲(Agriotes linneatus)、小麥金針蟲(Agriotes mancus)、外米擬步行蟲(Alphitobius diaperinus)、六月金龜(Amphimallon solstitialis)、傢俱竊蠹(Anobium punctatum)、天牛屬(Anoplophora spp.),例如光肩星天牛(Anoplophora glabripennis)、象甲屬(Anthonomus spp.),例如苜蓿葉象甲(Anthonomus grandis)、皮蠹屬(Anthrenus spp.)、種籽象甲屬(Apion spp.)、甘蔗金龜屬(Apogonia spp.)、寶螺屬(Atomaria spp.),例如甜菜隱食甲(Atomaria linearis)、黑皮蠹屬(Attagenus spp.)、白樹蠹(Baris caerulescens)、豌豆象(Bruchidius obtectus)、豆象屬(Bruchus spp.),例如豌豆象(Bruchus pisorum)、蠶豆象(Bruchus rufimanus),龜金花蟲屬(Cassida spp.)、豆葉甲蟲(Cerotoma trifurcata)、金龜屬(Ceutorrhynchus spp.),例如甘藍莢象甲(Ceutorrhynchus assimilis)、油菜莢象甲(Ceutorrhynchus quadridens)、蕪菁象甲(Ceutorrhynchus rapae)、跳甲屬(Chaetocnema spp.),例如甘薯金花蟲(Chaetocnema confinis)、具齒跳甲(Chaetocnema denticulata)、荒地玉米跳甲(Chaetocnema ectypa)、牛蒡象甲(Cleonus mendicus)、金針蟲屬(Conoderus spp.)、象鼻蟲屬(Cosmopolites spp.),例如香蕉球莖象鼻蟲(Cosmopolites sordidus)、草蛆(Costelytra zealandica)、叩頭甲蟲屬(Ctenicera spp.)、象蟲屬(Curculio spp.),例如核桃象甲(Curculio caryae)、大栗象甲(Curculio caryatrypes)、榛子象甲 (Curculio obtusus)、栗小象甲(Curculio sayi)、銹赤扁穀盜(Cryptolestes ferrugineus)、角胸粉扁蟲(Cryptolestes pusillus)、楊乾象(Cryptorhynchus lapathi)、芒果隱喙象甲(Cryptorhynchus mangiferae),細枝象屬(Cylindrocopturus spp.)、密點細枝象(Cylindrocopturus adspersus)、黃杉枝象(Cylindrocopturus furnissi)、小蠹蟲(Dendroctonus spp.),例如中歐山松大小蠹(Dendroctonus ponderosae),皮蠹屬(Dermestes spp.)、葉甲屬(Diabrotica spp.),例如帶斑黃瓜葉甲(Diabrotica balteata)、北方玉米根蟲(Diabrotica barberi)、南方玉米根蟲(Diabrotica undecimpunctata howardi)、黃瓜十一星葉甲(Diabrotica undecimpunctata undecimpunctata)、玉米根螢葉甲(Diabrotica virgifera virgifera)、墨西哥玉米根葉甲(Diabrotica virgifera zeae),蛀螟屬(Dichocrocis spp.)、稻鐵甲蟲(Dicladispa armigera)、兜蟲屬(Diloboderus spp.)、芽象甲屬(Epicaerus spp.)、瓢蟲屬(Epilachna spp.),例如南瓜瓢蟲(Epilachna borealis)、墨西哥豆瓢蟲(Epilachna varivestis),跳甲屬(Epitrix spp.),例如美洲馬鈴薯跳甲(Epitrix cucumeris)、茄跳甲(Epitrix fuscula)、煙草跳甲(Epitrix hirtipennis)、美國馬鈴薯跳甲(Epitrix subcrinita)、塊莖跳甲(Epitrix tuberis)、象鼻蟲(Faustinus spp.)、麥珠甲(Gibbium psylloides)、闊角榖盜(Gnathocerus cornutus)、菜心螟(Hellula undalis)、異爪黑金龜(Heteronychus arator)、金龜子屬(Heteronyx spp.)、小麥白蛆(Hylamorpha elegans)、家天牛(Hylotrupes bajulus)、苜蓿葉象甲(Hypera postica)、藍綠象(Hypomeces squamosus)、小蠹屬(Hypothenemus spp.),例如咖啡果小蠹(Hypothenemus hampei)、蘋枝小蠹(Hypothenemus obscurus)、毛咪小蠹(Hypothenemus pubescens)、甘蔴大褐齒爪魚思金龜(Lachnosterna consanguinea)、菸甲蟲(Lasioderma serricorne)、長頭榖盜(Latheticus oryzae)、薪甲屬(Lathridius spp.)、負泥甲屬(Lema spp.)、馬鈴薯甲蟲(Leptinotarsa decemlineata)、潛葉蛾屬(Leucoptera spp.),例如咖啡潛葉蛾(Leucoptera coffeella),凹形金針蟲(Limonius ectypus)、水稻水象鼻 蟲(Lissorhoptrus oryzophilus)、蔔象屬(Listronotus(=Hyperodes)spp.)、筒味象屬(Lixus spp.)、三葉草葉甲屬(Luperodes spp.)、黃胸寡毛跳甲(Luperomorpha xanthodera)、粉蠹屬(Lyctus spp.)、縊虎天牛屬(Megacyllene spp.),例如刺槐縊虎天牛(Megacyllene robiniae),金針蟲屬(Megascelis spp.)、叩頭蟲屬(Melanotus spp.),例如(Melanotus longulus oregonensis)、油菜花露尾甲(Meligethes aeneus)、鰓角金龜屬(Melolontha spp.),例如大栗鰓角金龜(Melolontha melolontha)、螟蟲屬(Migdolus spp.)、天牛屬(Monochamus spp.)、葡萄短鬚蟎(Naupactus xanthographus)、郭公蟲屬(Necrobia spp.)、小螢時甲屬(Neogalerucella spp.)、黃蛛甲蟲(Niptus hololeucus)、椰子犀角金龜(Oryctes rhinoceros)、鋸胸粉扁蟲(Oryzaephilus surinamensis)、葡萄黑耳喙象(Oryzaphagus oryzae)、象鼻蟲屬(Otiorhynchus spp.),例如蘋果白象(Otiorhynchus cribricollis)、苜蓿象鼻蟲(Otiorhynchus ligustici)、草莓耳喙象(Otiorhynchus ovatus)、草莓根耳喙象(Otiorhynchus rugosostriarus)、黑脈象鼻蟲(Otiorhynchus sulcatus)、負泥蟲屬(Oulema spp.),例如黑角負泥蟲(Oulema melanopus)、稻負泥蟲(Oulema oryzae)、銀點花金龜(Oxycetonia jucunda)、辣根猿葉甲(Phaedon cochleariae)、鰓角金龜屬(Phyllophaga spp.)、劍鰓角金龜(Phyllophaga helleri)、葉蚤屬(Phyllotreta spp.),例如辣根猿葉蟲(Phyllotreta armoraciae)、芥菜甲蟲(Phyllotreta pusilla)、西部條跳甲(Phyllotreta ramosa)、黃條葉蚤(Phyllotreta striolata)、日本金龜子(Popillia japonica)、安第斯馬鈴薯象屬(Premnotrypes spp.)、大穀蠹(Prostephanus truncatus)、蚤甲蟲屬(Psylliodes spp.),例如馬鈴薯跳甲(Psylliodes affinis)、油菜金頭跳甲(Psylliodes chrysocephala)、忽布跳甲(Psylliodes punctulata)、蜘甲屬(Ptinus spp.)、黑根瓢蟲(Rhizobius ventralis)、穀蠹(Rhizopertha dominica)、隱喙象屬(Rhynchophorus spp.)、椰子大象鼻蟲(Rhynchophorus ferrugineus)、棕櫚象甲(Rhynchophorus palmarum)、六齒長蠹蟲(Sinoxylon perforans)、小蠹屬(Scolytus spp.),例 如歐洲大榆小蠹(Scolytus multistriatus),倉儲稻穀象鼻蟲屬(Sitophilus spp.),例如榖象蟲(Sitophilus granarius)、羅望子象(Sitophilus linearis)、米象鼻蟲(Sitophilus oryzae)、玉米象(Sitophilus zeamais)、尖隱味象屬(Sphenophorus spp.)、藥材甲(Stegobium paniceum)、莖象屬(Sternechus spp.),例如豆莖象(Sternechus paludatus)、扁肩象屬(Symphyletes spp.)、黃粉甲屬(Tanymecus spp.),例如玉米葉象(Tanymecus dilaticollis)、印度玉米葉象(Tanymecus indicus)、甜菜灰色象蟲(Tanymecus palliatus)、黃粉蟲(Tenebrio molitor)、大穀盜(Tenebrioides mauretanicus)、擬穀盜屬(Tribolium spp.),例如黑粉甲(Tribolium audax)、擬榖盜(Tribolium castaneum)、扁擬榖盜(Tribolium confusum),斑皮蠹屬(Trogoderma spp.)、籽象屬(Tychius spp.)、虎天牛屬(Xylotrechus spp.)、距步甲屬(Zabrus spp.),例如玉米距步甲(Zabrus tenebrioides);來自革翅目(Dermaptera),例如蠼螋(Anisolabis maritime)、歐洲球螋(Forficula auricularia)、溪岸蠼螋(Labidura riparia);來自雙翅目(Diptera),例如伊蚊屬(Aedes spp.),例如埃及伊蚊(Aedes aegypti)、白紋伊蚊(Aedes albopictus)、叮刺伊蚊(Aedes sticticus)、騷擾伊蚊(Aedes vexans)、潛蠅屬(Agromyza spp.),例如苜蓿潛蠅(Agromyza frontella)、玉米斑潛蠅(Agromyza parvicornis)、按實蠅屬(Anastrepha spp.)、瘧蚊屬(Anopheles spp.),例如四斑按蚊(Anopheles quadrimaculatus)、甘比亞瘧蚊(Anopheles gambiae)、花椒波癭蚊屬(Asphondylia spp.)、實蠅屬(Bactrocera spp.),例如瓜實蠅(Bactrocera cucurbitae)、東方果實蠅(Bactrocera dorsalis)、橄欖果實蠅(Bactrocera oleae)、毛蚊(Bibio hortulanus)、紅顏紅眼蠅(Calliphora erythrocephala)、紅頭麗蠅(Calliphora vicina)、地中海果實蠅(Ceratitis capitata)、搖蚊屬(Chironomus spp.)、麗蠅屬(Chrysomya spp.)、金蠅屬(Chrysops spp.)、高額麻虻(Chrysozona pluvialis)、錐蠅屬(Cochliomyia spp.)、癭蚊屬 (Contarinia spp.),例如葡萄癭蚊(Contarinia johnsoni)、甘藍癭蚊(Contarinia nasturtii)、梨癭蚊(Contarinia pyrivora)、向日葵癭蚊(Contarinia schulzi)、高粱癭蚊(Contarinia sorghicola)、麥黃吸漿蟲(Contarinia tritici)、芒果蠅(Cordylobia anthropophaga)、樹真環足搖蚊(Cricotopus sylvestris)、家蚊屬(Culex spp.),例如尖音庫蚊(Culex pipiens)、五帶淡色庫蚊(Culex quinquefasciatus)、庫蠓屬(Culicoides spp.)、脈毛蚊屬(Culiseta spp.)、黃蠅屬(Cuterebra spp.)、橄欖蠅(Dacus oleae)、棗葉癭蚊屬(Dasineura spp.),例如蕓薹莢癭蚊(Dasineura brassicae)、地種蠅屬(Delia spp.),例如蔥蠅(Delia antiqua)、麥種蠅(Delia coarctata)、毛跗地種蠅(Delia florilega)、歐洲花蠅(Delia platura)、菜蛆(Delia radicum)、人皮蠅(Dermatobia hominis)、果蠅屬(Drosophila spp.),例如黃猩猩果蠅(Drosphila melanogaster)、日本斑翅果蠅(Drosophila suzukii)、象鼻蟲屬(Echinocnemus spp.)、實蠅(Euleia heraclei)、廁蠅屬(Fannia spp.)、胃蠅屬(Gasterophilus spp.)、采采蠅屬(Glossina spp.)、麻翅虻屬(Haematopota spp.)、稻心蠅屬(Hydrellia spp.)、水稻潛葉蠅(Hydrellia griseola)、黑蠅屬(Hylemyia spp.)、虱蠅屬(Hippobosca spp.)、皮蠅屬(Hypoderma spp.)、斑潛蠅屬(Liriomyza spp.),例如菜斑潛蠅(Liriomyza brassicae)、南美斑潛蠅(Liriomyza huidobrensis)、蔬菜斑潛蠅(Liriomyza sativae)、綠蠅屬(Lucilia spp.),例如銅綠蠅(Lucilia cuprina)、沙蠅屬(Lutzomyia spp.)、沼蚊屬(Mansonia spp.)、家蠅屬(Musca spp.),例如家蠅(Musca domestica)、舍蠅(Musca domestica vicina)、羊狂蠅屬(Oestrus spp.)、瑞典蠅(Oscinella frit)、擬長跗搖蚊屬(Paratanytarsus spp.)、小菱帕拉波尼蟲(Paralauterborniella subcincta)、甜菜潛葉蠅屬(Pegomya或Pegomyia spp.),例如甜菜泉蠅(Pegomya betae)、甜菜潛葉蠅(Pegomya hyoscyami)、懸鉤子泉蠅(Pegomya rubivora)、白蛉屬(Phlebotomus spp.)、草種蠅屬(Phorbia spp.)、伏蠅屬(Phormia spp.)、酪蠅(Piophila casei)、蘆筍實蠅(Platyparea poeciloptera)、 (Prodiplosis spp.)、胡蘿蔔蠅(Psila rosae)、繞實蠅屬(Rhagoletis spp.),例如北美櫻桃實蠅(Rhagoletis cingulata)、櫻桃白帶實蠅(Rhagoletis completa)、櫻挑黑果蠅(Rhagoletis fausta)、西部櫻桃實蠅(Rhagoletis indifferens)、越橘繞實蠅(Rhagoletis mendax)、蘋果果實蠅(Rhagoletis pomonella)、肉蠅屬(Sarcophaga spp.)、蚋屬(Simulium spp.),例如南方蚋(Simulium meridionale)、廄蠅屬(Stomoxys spp.)、牛虻屬(Tabanus spp.)、直斑蠅屬(Tetanops spp.)、歐洲大蚊屬(Tipula spp.),例如歐洲大蚊(Tipula paludosa)、牧場大蚊(Tipula simplex)、木瓜實蠅(Toxotrypana curvicauda);來自半翅目(Hemiptera),例如豆木蝨(Acizzia acaciaebaileyanae)、木蝨(Acizzia dodonaeae)、洋槐粉蝨(Acizzia uncatoides)、長頭蝗(Acrida turrita)、無網長管蚜屬(Acyrthosipon spp.),例如碗豆蚜(Acyrthosiphon pisum)、金花蟲屬(Acrogonia spp.)、稻褐飛虱屬(Aeneolamia spp.)、隆脈木虱屬(Agonoscena spp.)、粉虱屬(Aleurocanthus spp.)、歐洲甘藍粉蝨(Aleyrodes proletella)、甘蔗穴粉蝨(Aleurolobus barodensis)、棉絮粉蝨(Aleurothrixus floccosus)、榴蓮木蝨(Allocaridara malayensis)、小綠葉蟬屬(Amrasca spp.),例如小綠葉蟬(Amrasca bigutulla)、小葉蟬(Amrasca devastans)、李薊圓尾蚜(Anuraphis cardui)、介殼蟲屬(Aonidiella spp.),例如橘紅腎圓盾介殼蟲(Aonidiella aurantii)、橘黃腎圓盾介殼蟲(Aonidiella citrina)、木瓜腎圓盾介殼蟲(Aonidiella inornata)、梨瘤蚜(Aphanostigma piri)、豆蚜屬(Aphis spp.),例如橘捲菜蚜(Aphis citricola)、豆蚜(Aphis craccivora)、蚜蟲(Aphis fabae)、草莓根蚜(Aphis forbesi)、大豆蚜(Aphis glycines)、綿蚜(Aphis gossypii)、常春藤蚜(Aphis hederae)、葡萄蔓蚜(Aphis illinoisensis)、飛蓬根蚜(Aphis middletoni)、鼠李馬鈴薯蚜(Aphis nasturtii)、夾竹桃蚜(Aphis nerii)、蘋果蚜(Aphis pomi)、芹菜蚜(Aphis spiraecola)、莢迷蚜(Aphis viburniphila)、葉蟬(Arboridia apicalis)、Arytainilla spp.、小圓盾介殼蟲屬(Aspidiella spp.)、盾介殼蟲屬(Aspidiotus spp.),例 如夾竹桃圓蚧(Aspidiotus nerii)、按天蟲屬(Atanus spp.)、馬鈴薯蚜(Aulacorthum solani)、煙草粉蝨(Bemisia tabaci)、澳大利亞木蝨(Blastopsylla occidentalis)、白千層木蝨(Boreioglycaspis melaleucae)、光管舌尾蚜(Brachycaudus helichrysii)、微管蚜屬(Brachycolus spp.)、甘藍蚜(Brevicoryne brassicae)、嘻木蝨屬(Cacopsylla spp.),例如黃木蝨(Cacopsylla pyricola)、小褐稻虱(Calligypona marginata)、毒蜘蛛屬(Capulinia spp.)、紅頭大葉蟬(Carneocephala fulgida)、甘蔗綿蚜(Ceratovacuna lanigera)、沬蟬科(Cercopidae)、角蠟蚧屬(Ceroplastes spp)、草莓釘蚜(Chaetosiphon fragaefolii)、蔗黃雪盾蚧(Chionaspis tegalensis)、茶綠葉蟬(Chlorita onukii)、棉蝗(Chondracris rosea)、核桃黑斑蚜(Chromaphis juglandicola)、褐圓盾介殼蟲屬(Chrysomphalus aonidum)、褐圓介殼蟲(Chrysomphalus ficus)、假眼小綠葉蟬(Cicadulina mbila)、葛根貝盾階(Coccomytilus halli)、褐軟蚧屬(Coccus spp.),例如扁堅介殼蟲(Coccus hesperidum)、長堅介殼蟲(Coccus longulus)、橘灰蚧(Coccus pseudomagnoliarum)、黃綠介殼蟲(Coccus viridis)、黑茶藨隱瘤額蚜(Cryptomyzus ribis)、黃木虱屬(Cryptoneossa spp.)、木虱屬(Ctenarytaina spp.)、葉蟬屬(Dalbulus spp.)、杜鵑粉虱(Dialeurodes chittendeni)、柑桔裸粉蝨(Dialeurodes citri)、柑橘木蝨(Diaphorina citri)、介殼蟲屬(Diaspis spp.)、麥蚜屬(Diuraphis spp.)、Doralis spp.、草履介殼蟲屬(Drosicha spp.)、圓尾蚜屬(Dysaphis spp.),例如銹條蚜蚜(Dysaphis apiifolia)、玫瑰蘋果蚜(Dysaphis plantaginea)、鬱金香鱗莖蚜蟲(Dysaphis tulipae)、嫡粉介殼蟲屬(Dysmicoccus spp.)、棉花小綠葉蟬屬(Empoasca spp.),例如西部馬鈴薯微葉蟬(Empoasca abrupta)、馬鈴薯小綠葉蟬(Empoasca fabae)、蘋果小綠葉蟬(Empoasca maligna)、茄微葉蟬(Empoasca solana)、史迪浮塵子(Empoasca stevensi)、蘋果棉蚜屬(Eriosoma spp.),例如美洲榆綿蚜(Eriosoma americanum)、蘋果綿蚜(Eriosoma lanigerum)、梨根綿蚜(Eriosoma pyricola)、斑葉蟬屬(Erythroneura spp.)、 象甲屬(Eucalyptolyma spp.)、褐木蝨屬(Euphyllura spp.)、雙葉殃葉蟬(Euscelis bilobatus)、粉絲介殼蟲屬(Ferrisia spp.)、單銳盾蟲屬(Fiorinia spp.)、角盾蚧(Furcaspis oceanica)、咖啡荒粉蚧(Geococcus coffeae)、盾木蝨屬(Glycaspis spp.)、銀合歡木蝨(Heteropsylla cubana)、頰木蝨(Heteropsylla spinulosa)、褐透翅尖頭大葉蟬(Homalodisca coagulata)、桃大尾蚜(Hyalopterus arundinis)、桃粉蚜(Hyalopterus pruni)、吹棉介殼蟲屬(Icerya spp.),例如吹綿介殼蟲(Icerya purchasi)、黑胸葉蟬屬(Idiocerus spp.)、葉蟬屬(Idioscopus spp.)、斑飛蝨(Laodelphax striatellus)、蠟蚧屬(Lecanium spp.),例如歐洲水果介殼蟲(Lecanium corni(=Parthenolecanium corni))、黑絲盾蚧屬(Lepidosaphes spp.),例如榆蠣盾介殼蟲(Lepidosaphes ulmi)、偽菜蚜(Lipaphis erysimi)、日本長片盾介殼蟲(Lopholeucaspis japonica)、斑衣蠟蟬(Lycorma delicatula)、長管蚜屬(Macrosiphum spp.),例如馬鈴薯網管蚜(Macrosiphum euphorbiae)、紫斑長管蚜(Macrosiphum lilii)、薔薇長管蚜(Macrosiphum rosae)、二點葉蜂(Macrosteles facifrons)、沫蝶屬(Mahanarva spp.)、高粱蚜(Melanaphis sacchari)、角蟬屬(Metcalfiella spp.)、蛾錯蜂(Metcalfa pruinosa)、麥無網長管蚜(Metopolophium dirhodum)、黑緣平翅斑蚜(Monellia costalis)、核桃黃蚜(Monelliopsis pecanis)、蚜蟲屬(Myzus spp.),例如蔥蚜(Myzus ascalonicus)、黑櫻桃蚜(Myzus cerasi)、女貞瘤額蚜(Myzus ligustri)、堇菜瘤蚜(Myzus ornatus)、桃蚜(Myzus persicae)、煙草蚜蟲(Myzus nicotianae)、萵苣蚜(Nasonovia ribisnigri)、粉蝨屬(Neomaskellia spp.)、黑尾葉蟬屬(Nephotettix spp.),例如黑尾葉蟬(Nephotettix cincticeps)、黑條黑尾葉蟬(Nephotettix nigropictus)、稻水象甲(Nettigoniclla spectra)、褐飛蝨(Nilaparvata lugens)、大葉蟬屬(Oncometopia spp.)、狌蚧(Orthezia praelonga)、中華稻蝗(Oxya chinensis)、芽瘦木虱屬(Pachypsylla spp.)、粉蝨(Parabemisia myricae)、木虱屬(Paratrioza spp.),例如番茄虱(Paratrioza cockerelli)、黑星蚧屬(Parlatoria spp.)、楊癭棉蚜屬(Pemphigus spp.),例如囊柄癭綿蚜(Pemphigus bursarius)、甜菜多脈癭綿蚜(Pemphigus populivenae)、玉米飛蝨(Peregrinus maidis)、飛虱屬(Perkinsiella spp.)、棉粉蚧屬(Phenacoccus spp.),例如美地綿粉介殼蟲(Phenacoccus madeirensis)、楊平翅棉蚜(Phloeomyzus passerinii)、蛇麻草蚜(Phorodon humuli)、根瘤蚜屬(Phylloxera spp.),例如美核桃根瘤蚜(Phylloxera devastatrix)、薄殼山核桃瘤蚜(Phylloxera notabilis)、柑桔並盾介殼蟲(Pinnaspis aspidistrae)、粉介殼蟲屬(Planococcus spp.),例如柑桔粉介殼蟲(Planococcus citri)、柑橘木虱(Prosopidopsylla flava)、厚綠原綿介殼蟲(Protopulvinaria pyriformis)、桑介殼蟲(Pseudaulacaspis pentagona)、禾草粉蚧屬(Pseudococcus spp.),例如柑桔棲粉介殼蟲(Pseudococcus calccolariae)、康氏粉介殼蟲(Pseudococcus comstocki)、長尾粉介殼蟲(Pscudococcus longispinus)、海粉蚧(Pseudococcus maritimus)、白虱(Pseudococcus viburni)、榕屬木虱(Psyllopsis spp.)、木虱屬(Psylla spp.),例如黃楊木虱(Psylla buxi)、蘋木虱(Psylla mali)、梨木虱(Psylla pyri)、風蝶金小蜂屬(Pteromalus spp.)、綿介殼蟲屬(Pulvinaria spp.)、普路沙璐蠟蟬屬(Pyrilla spp.)、圓蚧屬(Quadraspidiotus spp.),例如福氏梨圓蚧(Quadraspidiotus juglansregiae)、歐洲果圓蚧(Quadraspidiotus ostreaeformis)、梨齒盾介殼蟲(Quadraspidiotus perniciosus)、爺蟬(Quesada gigas)、平粉介殼蟲屬(Rastrococcus spp.)、縊管蚜屬(Rhopalosiphum spp.),例如玉米蚜(Rhopalosiphum maidis)、蘋草縊管蚜(Rhopalosiphumoxyacanthae)、稻麥蚜(Rhopalosiphum padi)、紅腹縊管蚜(Rhopalosiphum rufiabdominale)、硬介殼蟲屬(Saissetia spp.),例如咖啡硬介殼蟲(Saissetia coffeae)、糖梳硬介殼蟲(Saissetia miranda)、黑光硬介殼蟲硬介殼蟲(Saissetia neglecta)、工背硬介殼蟲(Saissetia oleae)、葡萄帶葉蟬(Scaphoideus titanus)、綠蚜(Schizaphis graminum)、刺盾蚧(Selenaspidus articulatus)、黃偽毛蚜(Sipha flava)、麥長管蚜(Sitobion avenae)、白背飛虱屬(Sogata spp.)、背飛蝨(Sogatella furcifera)、飛虱屬(Sogatodes spp.)、沫蟬(Stictocephala festina)、梣木粉蝨(Siphoninus phillyreae)、木虱(Tenalaphara malayensis)、木虱屬(Tetragonocephela spp.)、胡桃黑蚜(Tinocallis caryaefoliae)、沫蟬屬(Tomaspis spp.)、蚜屬(Toxoptera spp.),例如小桔蚜(Toxoptera aurantii)、大桔蚜(Toxoptera citricidus)、溫室粉蝨(Trialeurodes vaporariorum)、木虱屬(Trioza spp.),例如柿木虱(Trioza diospyri)、小葉蟬屬(Typhlocyba spp.)、介殼蟲屬(Unaspis spp.)、蘋果小食心蟲(Viteus vitifolii)、葉蟬屬(Zygina spp.);來自異翅亞目(Heteroptera),例如蝽象屬(Aelia spp.)、南瓜緣蝽(Anasa tristis)、擬麗蜂屬(Antestiopsis spp.)、紅緣蝽屬(Boisea spp.)、土長蝽屬(Blissus spp.)、俊盲蜂屬(Calocoris spp.)、盲蝽(Campylomma livida)、二尾蚜屬(Cavelerius spp.)、臭蟲屬(Cimex spp.),例如(Cimex adjunctus)、熱帶臭蟲(Cimex hemipterus)、溫帶臭蟲(Cimex lectularius)、蝠臭蟲(Cimex pilosellus)、莖姬蜂屬(Collaria spp.)、綠盲蝽(Creontiades dilutus)、胡椒緣蝽(Dasynus piperis)、二葉喙蝽(Dichelops furcatus)、厚式長棒網蝽(Diconocoris hewetti)、棉紅蝽屬(Dysdercus spp.)、臭蝽屬(Euschistus spp.),例如大豆褐蝽(Euschistus heros)、褐臭蝽(Euschistus servus)、暗淡蝽象(Euschistus tristigmus)、點褐蝽(Euschistus variolarius)、菜蝽屬(Eurydema spp.)、刺蝽屬(Eurygaster spp.)、褐翅蝽象(Halyomorpha halys)、蚊子臭蟲(Heliopeltis spp.)、臭蟲(Horcias nobilellus)、豬緣蝽屬(Leptocorisa spp.)、稻緣蝽象(Leptocorisa varicornis)、西部喙緣蝽(Leptoglossus occidentalis)、葉足緣蝽(Leptoglossus phyllopus)、麗盲蝽屬(Lygocoris spp.),例如原麗盲蝽(Lygocoris pabulinus)、盲蝽屬(Lygus spp.),例如白豆盲蝽(Lygus elisus)、日本草盲蝽(Lygus hesperus)、豆莢草盲蝽(Lygus lineolaris)、蔗黑長蝽(Macropes excavatus)、篩豆龜蝽(Megacopta cribraria)、盲蝽科 (Miridae)、金光綠盲蝽(Monalonion atratum)、綠椿象屬(Nezara spp.),例如南方綠蝽(Nezara viridula)、小長蝽屬(Nysius spp.)、盾蝽屬(Oebalus spp.)、蝽科(Pentomidae)、蝽象(Piesma quadrata)、壁蝽屬(Piezodorus spp.),例如紅蝽(Piezodorus guildinii)、棉跳盲蝽屬(Psallus spp.)、花邊臭蟲(Pseudacysta persea)、錐鼻蟲屬(Rhodnius spp.)、褐盲(Sahlbergella singularis)、栗花蝽象(Scaptocoris castanea)、黑椿象屬(Scotinophora spp.)、梨冠軍配蟲(Stephanitis nashi)、臭蟲屬(Tibraca spp.)、錐鼻蟲屬(Triatoma spp.);來自膜翅目(Hymenoptera),例如切葉蟻屬(Acromyrmex spp.)、菜葉蜂屬(Athalia spp.),例如紅角菜葉蜂(Athalia rosae)、切葉蟻屬(Atta spp.)、巨山蟻屬(Camponotus spp.)、胡蜂屬(Dolichovespula spp.)、松葉蜂屬(Diprion spp.),例如白松葉蜂(Diprion similis)、李葉蜂屬(Hoplocampa spp.),例如櫻實葉蜂(Hoplocampa cookei)、蘋實葉蜂(Hoplocampa testudinea)、毛蟻屬(Lasius spp.)、阿根廷蟻(Linepithema(Iridiomyrmex)humile)、小黃單家蟻(Monomorium pharaonis)、黃山蟻屬(Paratrechina spp.)、黃蜂屬(Paravespula spp.)、箭蟻屬(Plagiolepis spp.)、樹蜂屬(Sirex spp.),例如雲杉藍樹蜂(Sirex noctilio),紅火蟻(Solenopsis invicta)、酸臭蟻(Tapinoma spp.)、白足扁琉璃蟻(Technomyrmex albipes)、大樹蜂屬(Urocerus spp.)、虎頭蜂屬(Vespa spp.),例如黃邊胡蜂(Vespa crabro)、小火蟻(Wasmannia auropunctata)、黑樹蜂屬(Xeris spp.);來自等足目(Isopoda),例如鼠婦(Armadillidium vulgare)、壁潮蟲(Oniscus asellus)、粗礪潮蟲(Porcellio scaber);來自等翅目(Isoptera),例如乳白蟻屬(Coptotermes spp.),例如家白蟻(Coptotermes formosanus)、堆角白蟻(Cornitermes cumulans)、堆沙白蟻屬(Cryptotermes spp.)、楹白蟻屬(Incisitermes spp.)、木白蟻屬(Kalotermes spp.)、甘蔗白蟻(Microtermes obesi)、象白蟻屬(Nasutitermes spp.)、黑翅 土白蟻屬(Odontotermes spp.)、盲白蟻屬(Porotermes spp.)、網白蟻屬(Reticulitermes spp.),例如黃肢散白蟻(Reticulitermes flavipes)、西方犀白蟻(Reticulitermes hesperus);來自鱗翅目(Lepidoptera),例如小蠟螟(Achroia grisella)、桑劍紋夜蛾(Acronicta major)、捲葉蛾屬(Adoxophyes spp.),例如茶姬捲葉蛾(Adoxophyes orana)、白斑煩夜蛾(Aedia leucomelas)、地老虎屬(Agrotis spp.),例如黃地老虎(Agrotis segetum)、球菜夜蛾(Agrotis ipsilon)、阿拉巴馬屬(Alabama spp.),例如棉葉波紋葉蛾(Alabama argillacea)、臍橙螟(Amyelois transitella)、條麥蛾屬(Anarsia spp.)、夜蛾屬(Anticarsia spp.),例如大豆夜蛾(Anticarsia gemmatalis)、黃螟屬(Argyroploce spp.)、夜蛾屬(Autographa spp.)、甘藍夜蛾(Barathra brassicae)、蘋髓尖蛾(Blastodacna atra)、禾弄蝶(Borbo cinnara)、棉葉穿孔潛蛾(Bucculatrix thurberiella)、松尺蠖(Bupalus piniarius)、姓褐夜蛾屬(Busseola spp.)、捲蛾屬(Cacoecia spp.)、茶細蛾(Caloptilia theivora)、煙捲蛾(Capua reticulana)、蘋果蠹蟲(Carpocapsa pomonella)、桃蛀果蛾(Carposina niponensis)、尺蠖蛾(Cheimatobia brumata)、螟屬(Chilo spp.),例如星稻螟(Chilo plejadellus)、二化螟(Chilo suppressalis)、蘋果舞蛾(Choreutis pariana)、色捲蛾屬(Choristoneura spp.)、錁紋夜蛾(Chrysodeixis chalcites)、葡萄果蠹蛾(Clysia ambiguella)、捲螟屬(Cnaphalocerus spp.)、瘤野螟(Cnaphalocrocis medinalis)、雲捲蛾屬(Cnephasia spp.)、細蛾屬(Conopomorpha spp.)、球細頸象屬(Conotrachelus spp.)、小捲蛾屬(Copitarsia spp.)、蠹蛾屬(Cydia spp.),例如豆莢小捲蛾(Cydia nigricana)、蘋果蠹蛾(Cydia pomonella)、叢螟屬(Dalaca noctuides)、絹野螟屬(Diaphania spp.)、蘇丹棉鈴蟲屬(Diparopsis spp.)、小蔗螟(Diatraea saccharalis)、梢斑螟屬(Dioryctria spp.),例如齊氏梢斑螟(Dioryctria zimmermani),鑽夜蛾屬(Earias spp.)、射線對小 捲蛾(Ecdytolopha aurantium)、南美玉米苗斑螟(Elasmopalpus lignosellus)、莖螟(Eldana saccharina)、粉斑螟屬(Ephestia spp.),例如煙草粉螟(Ephestia elutella)、地中海粉螟(Ephestia kuehniella)、油松小捲蛾屬(Epinotia spp.)、淡褐蘋果蛾(Epiphyas postvittana)、尺蛾屬(Erannis spp.)、亞洲核桃蛾(Erschoviella musculana)、莢斑螟屬(Etiella spp.)、木葉蛾屬(Eudocima spp.)、掠捲蛾屬(Eulia spp.)、葡萄與蘋果捲葉蛾(Eupoecilia ambiguella)、黃毒蛾屬(Euproctis spp.),例如褐尾蛾(Euproctis chrysorrhoea)、切根蟲屬(Euxoa spp.)、褐夜蛾屬(Feltia spp.)、大蠟螟(Galleria mellonella)、細蛾屬(Gracillaria spp.)、小食心蟲屬(Grapholitha spp.),例如桃折心蟲(Grapholita molesta)、蘋小果蠹(Grapholita prunivora)、蝕葉野螟屬(Hedylepta spp.)、夜蛾屬(Helicoverpa spp.),例如番茄夜蛾(Helicoverpa armigera)、棉鈴蟲(Helicoverpa zea)、棉鈴蟲屬(Heliothis spp.),例如芽夜蛾(Heliothis virescens)、褐織夜蛾(Hofmannophila pseudospretella)、同斑螺屬(Homoeosoma spp.)、茶捲葉蛾屬(Homona spp.)、櫻桃巢蛾(Hyponomeuta padella)、柿蒂蟲(Kakivoria flavofasciata)、灰蝶屬(Lampides spp.)、夜蛾屬(Laphygma spp.)、梨小食心蟲(Laspeyresia molesta)、茄螟(Leucinodes orbonalis)、潛蛾屬(Leucoptera spp.),例如咖啡潛葉蛾(Leucoptera coffeella)、潛葉細蛾屬(Lithocolletis spp.),例如斑點幕形潛葉蛾(Lithocolletis blancardella)、綠果夜蛾(Lithophane antennata)、花翅小捲蛾屬(Lobesia spp.),例如葡萄漿果小捲蛾(Lobesia botrana)、西方豆地老虎(Loxagrotis albicosta)、舞毒蛾屬(Lymantria spp.),例如舞毒蛾(Lymantria dispar)、潛蛾屬(Lyonetia spp.),例如桃潛葉蛾(Lyonetia clerkella)、天幕枯葉蛾(Malacosoma neustria)、豆莢螟(Maruca testulalis)、甘藍夜蛾(Mamestra brassicae)、暮眼蝶(Melanitis leda)、毛腔夜蛾屬(Mocis spp.)、穀蛾科(Monopis obviella)、黏蟲(Mythimna separata)、橡長角蛾(Nemapogon cloacellus)、水螟屬(Nymphula spp.)、Oiketicus spp.、莖螟屬 (Omphisa spp.)、秋尺蛾屬(Operophtera spp.)、巫夜蛾屬(Oria spp.)、瘤叢螟屬(Orthaga spp.)、杆野螟屬(Ostrinia spp.),例如歐洲玉米螟(Ostrinia nubilalis)、冬夜蛾(Panolis flammea)、稻弄蝶屬(Parnara spp.)、棉紅鈴蟲屬(Pectinophora spp.),例如紅鈴蟲(Pectinophora gossypiella)、潛跳甲屬(Perileucoptera spp.)、煙尺蛾屬(Phthorimaea spp.),例如馬鈴薯塊莖蛾(Phthorimaea operculella)、桔潛蛾(Phyllocnistis citrella)、小潛細蛾屬(Phyllonorycter spp.),例如潛葉蟲(Phyllonorycter blancardella)、山楂潛葉蛾(Phyllonorycter crataegella)、菜粉蝶屬(Pieris spp.),例如白粉蝶(Pieris rapae)、荷蘭石竹小捲蛾(Platynota stultana)、印度穀蛾(Plodia interpunctella)、金翅夜蛾屬(Plusia spp.)、菜蛾(Plutella xylostella(=Plutella maculipennis))、Podesia spp.,例如Podesia syringae,小白巢蛾屬(Prays spp.)、斜紋夜蛾屬(Prodenia spp.)、煙草天蛾屬(Protoparce spp.)、擬粘葉蛾屬(Pseudaletia spp.),例如栗夜盜蛾(Pseudaletia unipuncta)、大豆夜蛾(Pseudoplusia includens)、玉米螟(Pyrausta nubilalis)、薄荷灰夜蛾(Rachiplusia nu)、禾螟屬(Schoenobius spp.),例如三化螟蟲(Schoenobius bipunctifer)、白禾螟屬(Scirpophaga spp.),例如水稻螟蛾(Scirpophaga innotata)、黃地老虎(Scotia segetum)、姓莖夜蛾屬(Sesamia spp.),例如稻蛀莖夜蛾(Sesamia inferens)、長鬚捲蛾屬(Sparganothis spp.)、灰翅夜蛾屬(Spodoptera spp.),例如亞熱帶黏蟲(Spodoptera eradiana)、甜菜夜蛾(Spodoptera exigua)、秋夜盜蛾(Spodoptera frugiperda)、西部黃條黏蟲(Spodoptera praefica)、舉肢蛾屬(Stathmopoda spp.)、梨織蛾屬(Stenoma spp.)、花生麥蛾(Stomopteryx subsecivella)、興透翅蛾屬(Synanthedon spp.)、安第斯馬鈴薯塊莖蛾(Tecia solanivora)、帶蛾屬(Thaumetopoea spp.)、幹煞夜蛾(Thermesia gemmatalis)、木塞穀蛾(Tinea cloacella)、袋穀蛾(Tinea pellioonella)、幕穀蛾(Tineola bisselliella)、捲蛾屬(Tortrix spp.)、毛顫蛾(Trichophaga tapetzella)、粉夜蛾屬(Trichoplusia spp.),例如粉紋夜 蛾(Trichoplusia ni)、三化螟(Tryporyza incertulas)、番煎斑潛蠅(Tuta absoluta)、灰蝶屬(Virachola spp.);來自直翅目(Orthoptera)或跳躍亞目(Saltatoria),例如家蟋蟀(Acheta domesticus)、Dichroplus spp.、螻蛄屬(Gryllotalpa spp.),例如東方螻蛄(Gryllotalpa gryllotalpa)、蔗蝗屬(Hieroglyphus spp.)、飛蝗屬(Locusta spp.),例如東亞飛蝗(Locusta migratoria)、黑蝗屬(Melanoplus spp.),例如赤地蚱蜢(Melanoplus devastator)、烏蘇裡擬寰螽(Paratlanticus ussuriensis)、沙漠飛蝗(Schistocerca gregaria);來自毛蝨目(Phthiraptera),例如毛虱屬(Damalinia spp.)、血蝨屬(Haematopinus spp.)、長顎蝨屬(Linognathus spp.)、虱蝨屬(Pediculus spp.)、葡萄根瘤蚜(Phylloxera vastatrix)、虱蝨(Phthirus pubis)、毛蝨屬(Trichodectes spp.);來自嚙蟲目(Psocoptera),例如書蝨屬(Lepinatus spp.)、書蝨屬(Liposcelis spp.);來自蚤目(Siphonapterida),例如禽蚤屬(Ceratophyllus spp.)、頭梳蚤屬(Ctenocephalides spp.),例如狗蚤(Ctenocephalides canis)、貓櫛頭蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、穿皮潛蚤(Tunga penetrans)、印度鼠蚤(Xenopsylla cheopis);來自纓翅目(Thysanoptera),例如黃呆薊馬(Anaphothrips obscurus)、稻薊馬(Baliothrips biformis)、中斑圍孔薊馬(Chaetanaphothrips leeuweni)、鮮食葡萄鐮薊馬(Drepanothrips reuteri)、黃薊馬(Enneothrips flavens)、花薊馬屬(Frankliniella spp.),例如煙草花薊馬(Frankliniella fusca)、西方花薊馬(Frankliniella occidentalis)、梳缺花薊馬(Frankliniella schultzei)、美東花薊馬(Frankliniella tritici)、越橘薊馬(Frankliniella vaccinii)、威廉斯花薊馬(Frankliniella williamsi)、玉米薊馬(Haplothrips spp.)、陽薊馬屬(Heliothrips spp.)、粟網薊馬(Hercinothrips femoralis)、卡薊馬屬(Kakothrips spp.)、腹 鉤薊馬(Rhipiphorothrips cruentatus)、硬薊馬屬(Scirtothrips spp.)、荳蔻薊馬(Taeniothrips cardamoni)、薊馬屬(Thrips spp.),例如南黃薊馬(Thrips palmi)、蔥薊馬(Thrips tabaci);來自衣魚目(Zygentoma)(=櫻尾目(Thysanura)),例如櫛衣魚屬(Ctenolepisma spp.)、衣魚(Lepisma saccharina)、盜火蟲(Lepismodes inquilinus)、斑衣魚(Thermobia domestica);來自結閥綱(Symphyla),例如麽蚰屬(Scutigerella spp.),例如白松蟲(Scutigerella immaculata);來自下列害蟲:軟體動物門,例如來自雙殼綱(Bivalvia),例如飾貝屬(Dreissena spp.);及來自腹足綱(Gastropoda),例如蛞蝓屬(Arion spp.),例如(Arion ater rufus)、紅扁蜷屬(Biomphalaria spp.)、泡螺屬(Bulinus spp.)、野蛞蝓屬(Deroceras spp.),例如(Deroceras laeve)、土蝸螺屬(Galba spp.)、椎實螺屬(Lymnaea spp.)、釘螺屬(Oncomelania spp.)、金蘋果螺屬(Pomacea spp.)、琥珀螺屬(Succinea spp.);來自下列害蟲:線形動物門,亦即植物寄生性線蟲,特別為野外墊刃屬(Aglenchus spp.),例如居農野外墊刃線蟲(Aglenchus agricola)、粒線蟲屬(Anguina spp.),例如小麥粒癭線蟲(Anguina tritici)、滑刃線蟲屬(Aphelenchoides spp.),例如花生滑刃線蟲(Aphelenchoides arachidis)、草莓滑刃線蟲(Aphelenchoides fragariae)、刺線蟲屬(Belonolaimus spp.),例如豌豆刺線蟲(Belonolaimus gracilis)、長尾刺線蟲(Belonolaimus longicaudatus)、諾頓剌線蟲(Belonolaimus nortoni)、傘滑刃線蟲屬(Bursaphelenchus spp.),例如椰子紅環腐線蟲(Bursaphelenchus cocophilus)、傘滑刃線蟲(Bursaphelenchus eremus)、松材線蟲(Bursaphelenchus xylophilus)、輪線蟲屬(Cacopaurus spp.),例如胡桃線蟲(Cacopaurus pestis)、環紋線蟲屬(Criconemella spp.),例如彎曲小環線蟲 (Criconemella curvata)、刻線小環線蟲(Criconemella onoensis)、裝飾小環線蟲(Criconemella ornata)、美洲山核桃環線蟲(Criconemella rusium)、薄葉小環線蟲(Criconemella xenoplax)(=環腐線蟲(Mesocriconema xenoplax))、小環線蟲屬(Criconemoides spp.),例如弗尼亞小環線蟲(Criconemoides ferniae)、小環線蟲(Criconemoides onoense)、杯口小環線蟲(Criconemoides ornatum)、莖線蟲屬(Ditylenchus spp.),例如莖線蟲(Ditylenchus dipsaci)、錐線蟲屬(Dolichodorus spp.)、黃金線蟲屬(Globodera spp.),例如馬鈴薯白線蟲(Globodera pallida)、馬鈴薯黃金線蟲(Globodera rostochiensis)、螺旋線蟲屬(Helicotylenchus spp.),例如雙宮螺旋線蟲(Helicotylenchus dihystera)、擬鞘線蟲屬(Hemicriconemoides spp.)、鞘線蟲屬(Hemicycliophora spp.)、異皮線蟲屬(Heterodera spp.),例如禾谷異皮線蟲(Heterodera avenae)、大豆異皮線蟲(Heterodera glycines)、甜菜異皮線蟲(Heterodera schachtii)、潛根線蟲屬(Hirschmaniella spp.)、紐帶線蟲屬(Hoplolaimus spp.)、長刺線蟲屬(Longidorus spp.),例如非洲長刺線蟲(Longidorus africanus)、根瘤線蟲屬(Meloidogyne spp.),例如奇氏根瘤線蟲(Meloidogyne chitwoodi)、擬禾本科根瘤線蟲(Meloidogyne fallax)、北方根瘤線蟲(Meloidogyne hapla)、南方根瘤線蟲(Meloidogyne incognita)、瓢線蟲屬(Meloinema spp.)、假根瘤線蟲屬(Nacobbus spp.)、擬莖線蟲屬(Neotylenchus spp.)、擬長針線蟲屬(Paralongidorus spp.)、擬滑刃線蟲(Paraphelenchus spp.)、擬毛刺線蟲屬(Paratrichodorus spp.),例如小擬毛刺線蟲(Paratrichodorus minor)、針線蟲屬(Paratylenchus spp.)、短體線蟲屬(Pratylenchus spp.),例如穿刺短體線蟲(Pratylenchus penetrans)、假海矛線蟲屬(Pseudohalenchus spp.)、平滑線蟲屬(Psilenchus spp.)、斑皮線蟲屬(Punctodera spp.)、五溝線蟲屬(Quinisulcius spp.)、穿孔線蟲屬(Radopholus spp.),例如柑橘穿孔線蟲(Radopholus citrophilus)、穿孔線蟲(Radopholus similis)、盤旋線蟲屬(Rotylenchulus spp.)、螺旋線蟲屬(Rotylenchus spp.)、 盾線蟲屬(Scutellonema spp.)、亞蛇形線蟲屬(Subanguina spp.)、毛刺線蟲屬(Trichodorus spp.),例如鈍毛刺線蟲(Trichodorus obtusus)、原始毛刺線蟲(Trichodorus primitivus)、矮化線蟲屬(Tylenchorhynchus spp.),例如矮化線蟲(Tylenchorhynchus annulatus)、鴕形線蟲屬(Tylenchulus spp.),例如柑桔寄生性線蟲(Tylenchulus semipenetrans)、劍線蟲屬(Xiphinema spp.),例如劍線蟲(Xiphinema index)。
式(I)化合物亦可視情況以特定濃度或施予率用作為改進植物性質的除草劑、安全劑、生長調節劑或生長劑,用作為殺微生物劑或殺配子劑,例如作為殺真菌劑、抗黴劑、殺細菌劑、殺病毒劑(包括對抗類病毒之劑),或作為對抗MLO(類黴漿菌有機體)及RLO(類立克次體有機體)之劑。彼此亦可視情況而用作為合成其他活性化合物之中間物或前驅物。
本發明進一步關於包含至少一種式(I)化合物之調配物及自其所製備的應用形式,用作為殺蟲劑,例如澆灌、滴藥水及噴灑液。應用形式可選擇地包含更多殺蟲劑及/或改進作用之佐劑,諸如滲透劑,例如植物油(例如菜籽油、葵花油)、礦物油(例如石蠟油)、植物脂肪酸之烷酯(例如菜籽油甲酯或大豆油甲酯)或烷醇烷氧化物,及/或擴散劑,例如烷基矽氧烷,及/或鹽,例如有機或無機銨或鏻鹽,例如硫酸銨或磷酸氫二銨,及/或促進滯留劑,例如磺基琥珀酸二辛酯或羥丙基膠豆聚合物,及/或保濕劑,例如甘油,及/或肥料,例如含銨-、鉀-或磷-之肥料。
習知的調配物為例如水溶性液體(SL)、乳化濃縮劑(EC)、水性乳液(EW)、懸浮濃縮劑(SC、SE、FS、OD)、水可分散性粒劑(WG)、粒劑(GR)及膠囊濃縮劑(CS);該等及更多可能的調配物類型說明於例如2004年以FAO/WHO Joint Meeting on Pesticide Specifications所製作之Crop Life International and in Pesticide Specifications,Manual on development and use of FAO and WHO specifications for pesticides,FAO Plant Production and Protection Papers-173),ISBN:9251048576。除了一或多種式(I)化合物以外,調配物可選擇地包含其他的農化活性化合物。
優先選擇為包含輔助劑的調配物或應用形式,例如增量劑、溶劑、自發性促進劑、載劑、乳化劑、分散劑、防凍劑、殺生物劑、增稠劑及/或其他輔助劑,例如佐劑。在本上下文中的佐劑為增強調配物的生物效應之組份,該組份本身不具有任何生物效應。佐劑的實例為促進滯留、擴散、附著於葉表面或滲透之劑。
該等調配物係以已知的方式製備,例如藉由將式(I)化合物與輔助劑混合,例如增量劑、溶劑及/或固體載劑及/或其他的輔助劑,例如介面活性劑。調配物係在適合的設備中或另外在施予前或期間製備。
所使用的輔助劑可為適合賦予式(I)化合物的調配物或由該等調配物所製得的應用形式(例如即用型殺蟲劑,諸如噴灑液或拌種產品)特定性質(諸如特定的物理、技術及/或生物性質)之物質。
適合的增量劑為例如水、極性和非極性有機化學液體,例如下列類別:芳族和非芳族烴(諸如石蠟、烷基苯、烷基萘、氯苯)、醇和多元醇(若適當時,其亦可經取代、醚化與/或酯化)、酮(諸如丙酮、環己酮)、酯(包括脂肪和油)及(聚)醚、簡單和經取代的胺、醯胺、內醯胺(諸如N-烷基吡咯啶酮)和內酯、碸及亞碸(諸如二甲基亞碸)。
若所使用的增量劑為水,則亦有可能使用例如有機溶劑作為輔助溶劑。有用的液體溶劑基本上為:芳族烴(諸如二甲苯、甲苯或烷基萘)、氯化芳族烴或氯化脂族烴(諸如氯苯、氯乙烯或二氯甲烷)、脂族烴(諸如環己烷或石蠟,例如石油分餾物、礦物油和植物油)、醇(諸如丁醇或二醇)及其醚和酯、酮(諸如丙酮、甲基乙酮、甲基異丁酮或環已酮)、強極性溶劑(諸如二甲基甲醯胺和二甲基亞碸),且亦為水。
原則上,有可能使用所有適合的溶劑。適合的溶劑之實例為芳族烴(例 如二甲苯、甲苯或烷基萘)、氯化芳族烴或氯化脂族烴(例如氯苯、氯乙烯或二氯甲烷)、脂族烴(例如環己烷、石蠟、石油分餾物、礦物油和植物油)、醇(例如甲醇、乙醇、異丙醇、丁醇或二醇)及其醚和酯、酮(例如丙酮、甲基乙酮、甲基異丁酮或環己酮)、強極性溶劑(例如二甲基亞碸),及水。
原則上,有可能使用所有適合的載劑。適合的載劑更特別包括下列者:例如銨鹽和細研磨之天然礦石(諸如高嶺土、黏土、滑石、白堊、石英、矽鎂土、蒙脫土或矽藻土)和細研磨之合成礦石(諸如細碎的矽石、氧化鋁和天然或合成矽酸鹽、樹脂、蠟及/或固體肥料)。同樣地,有可能使用此等載劑之混合物。有用於粒劑之載劑包括:例如粉碎且分級之天然礦石(諸如方解石、大理石、浮石、海泡石、白雲石及無機和有機穀粉之合成顆粒),及亦為有機材料顆粒(諸如鋸屑、紙、椰子殼、玉米穗軸和菸草稈)。
亦有可能使用液化氣態增量劑或溶劑。尤其適合的是那些在標準溫度下及在大氣壓力下呈氣態的增量劑或溶劑,例如氣霧推進氣體,諸如鹵化烴,及亦為丁烷、丙烷、氮氣和二氧化碳。
具有離子或非離子性質之乳化劑及/或發泡劑、分散劑或潤濕劑,或該等介面活性劑之混合物的實例為聚丙烯酸之鹽、木質素磺酸之鹽、苯酚磺酸或萘磺酸之鹽、環氧乙烷與脂肪醇或與脂肪酸或與脂肪胺或與經取代的苯酚(較佳為烷基苯酚或芳基苯酚)之聚縮合物、磺基琥珀酸酯之鹽、牛磺酸衍生物(較佳為牛磺酸烷酯)、聚乙氧基化醇或苯酚之磷酸酯、多元醇之脂肪酸酯,及含硫酸根、磺酸根和磷酸根之化合物的衍生物,例如烷基芳基聚二醇醚、烷基磺酸鹽、烷基硫酸鹽、芳基磺酸鹽、蛋白質水解物、木質素亞硫酸鹽廢液和甲基纖維素。若式(I)化合物中之一者及/或惰性載劑中之一者不溶於水中且若施予係發生在水中時,則介面活性劑的存在是有利的。
可存在於調配物及自其所衍生之應用形式中的更多輔助劑包括染料(諸如無機顏料,例如氧化鐵、氧化鈦和普魯士藍,及有機染料,諸如茜素染料、偶氮染料和金屬酞花青染料),及營養素和微量營養素(諸如鐵、錳、硼、 銅、鈷、鉬和鋅之鹽)。
可存在的額外組份為穩定劑(諸如低溫穩定劑)、防腐劑、抗氧化劑、光穩定劑或其他改進化學及/或物理穩定性之劑。亦可有發泡劑或消泡劑的存在。
另外,調配物及自其所衍生之應用形式亦可包含膠黏劑(諸如羧甲基纖維素及呈粉末、顆粒或膠乳形式的天然和合成聚合物,諸如阿拉伯膠、聚乙烯醇和聚乙酸乙烯酯),或其他的天然磷脂(諸如腦磷脂和卵磷脂)和合成磷脂作為額外的輔助劑。更多可能的輔助劑為礦物油和植物油。
若適當時、有可能以又更多的輔助劑存在於調配物及自其所衍生之應用形式中。此等添加劑的實例包括香料、保護性膠體、結合劑、黏著劑、增稠劑、搖溶劑、滲透劑、促進滯留劑、穩定劑、螯合劑、錯合組成物、保濕劑、擴散劑。通常可將式(I)化合物與常用於調配目的之任何固體或液體添加劑組合。
有用的促進滯留劑包括所有那些降低動態表面張力之物質,例如磺基琥珀酸二辛酯,或增加黏彈性之物質,例如羥丙基膠豆聚合物。
在本發明上下文中,有用的滲透劑為所有那些通常用於改進農化活性成分滲透至植物中的物質。在本發明上下文中,滲透劑係以其自(通常為水性)施予液體及/或自噴灑覆層滲透至植物的角質層且由此增加活性化合物在角質層中的移動性之能力來定義。可使用文獻中所述之方法(Baur等人之1997,Pesticide Science 51,131-152)來測定此性質。實例包括醇烷氧化物(諸如椰子脂肪乙氧化物(10)或異十三烷基乙氧化物(12))、脂肪酸酯(例如菜籽油甲酯或大豆油甲酯)、脂肪胺烷氧化物(例如獸脂胺乙氧化物(15))或銨及/或鏻鹽(例如硫酸銨或磷酸氫二銨)。
調配物較佳地包含以調配物重量為基準計介於0.00000001與98重量%之間的式(I)化合物,更佳為介於0.01與95重量%之間的式(I)化合物,最佳為介於0.5與90重量%之間的式(I)化合物。
在自調配物所製備之應用形式(特別為殺蟲劑)中的式(I)化合物含量可在寬廣的範圍內改變。在應用形式中的式(I)化合物濃度通常係以應用形式的重量為基準計介於0.00000001與95重量%之間的式(I)化合物,較佳為介於0.00001與1重量%之間。以適合於應用形式的習知方式完成施予。
式(I)化合物亦可用於與一種或多種適合的殺真菌劑、殺細菌劑、殺蟎劑、殺軟體動物劑、殺線蟲劑、殺昆蟲劑、微生物劑、有利物種、除草劑、肥料、驅鳥劑、植物強直劑(phytotonics)、滅菌劑、安全劑、化學傳訊素及/或植物生長調節劑之混合物中,以便於因此例如擴增廣效作用、延長作用時期、提高作用率、防止排斥或防止抗性進化。另外,此種纇的活性化合物組合可改進植物生長及/或對非生物因數(例如高或低溫、乾旱或升高的含水量或土壤鹽度)之耐受性,亦有可能改進開花和結果性能、優化發芽能力和根發育、加速收成和改進產率、影響成熟、改進收成產物之品質及/或營養價值、延長貯藏壽命及/或改進收成產物之加工性。
另外,式(I)化合物可存在於與其他的活性化合物或化學傳訊素之混合物中,諸如引誘劑及/或驅鳥劑及/或植物活化劑及/或生長調節劑及/或肥料。同樣地,可使用式(I)化合物改進植物性質,例如收成原料的生長、產率及品質。
在根據本發明特別的實施態樣中,式(I)化合物係存在於與更多化合物(較佳為那些下文所述者)之混合物的調配物中或自該等調配物所製備之應用形式中。
若下文所述化合物中之一者可以不同的互變異構物形式出現時,則亦包括該等形式,即使未於各例子中明確述及。所有述及之混合組份亦可視情況與適合的鹼或酸形成鹽,假設彼等係基於彼等的官能基而能夠因此達成。
在此以彼等的通用名稱具體指定之活性化合物為已知且說明於例如“The Pesticide Manual”16th Ed.,British Crop Protection Council 2012中或可於網路上搜尋(例如http://www.alanwood.net/pesticides)。分類係基於在申請此專利申請案時應用的作用分類方案之IRAM模式(IRAC Mode of Action Classification Scheme)。
(1)乙醯膽鹼酯酶(AChE)抑制劑,例如胺甲酸酯,例如亞拉克(alanycarb)、得滅克(aldicarb)、免敵克(bendiocarb)、免扶克(benfuracarb)、佈嘉信(butocarboxim)、丁氧喜信(butoxycarboxim)、加保利(carb芳基)、加保扶(carbofuran)、丁基加保扶(carbosulfan)、愛殺克(ethiofencarb)、丁基滅必蝨(fenobucarb)、覆滅滿(formetanate)、護拉克(furathiocarb)、滅必蝨(isoprocarb)、滅賜克(methiocarb)、納乃得(methomyl)、治滅蝨(metolcarb)、歐殺滅(oxamyl)、比加普(pirimicarb)、安丹(propoxur)、硫敵克(thiodicarb)、硫化隆(thiofanox)、三雜滅(triazamate)、三美克(trimethacarb)、XMC和滅爾蝨(xylylcarb);或有機磷酸酯,例如歐殺松(acephate)、雜美松(azamethiphos)、穀速松(azinphos)-乙酯、穀速松-甲酯、卡杜松(cadusafos)、氯乙氧松(chlor乙氧基fos)、氯芬松(chlorfenvinphos)、克美松(chlormephos)、陶斯松(chlorpyrifos)-甲酯、可馬松(coumaphos)、氰基松(氰基phos)、滅賜松(demeton)-S-甲酯、大利松(diazinon)、二氯松(dichlorvos)/DDVP、雙特松(dicrotophos)、大滅松(dimethoate)、二甲基芬松(dimethylvinphos)、二硫松(disulfoton)、EPN、愛殺松(ethion)、普伏松(ethoprophos)、胺磺磷(famphur)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬殺松(fenthion)、松賽殺(fosthiazate)、飛達松(heptenophos)、依米氰松(imicyafos)、亞芬松(isofenphos)、O-(甲氧胺基硫磷醯基)水楊酸異丙酯、加福松(isoxathion)、馬拉松(malathion)、滅加松(mecarbam)、達馬松(methamidophos)、滅大松 (methidathion)、美文松(mevinphos)、亞素靈(monocrotophos)、那列(naled)、歐滅松(omethoate)、滅多松(oxydemeton)-甲酯、巴拉松-甲酯、賽達松(phenthoate)、福瑞松(phorate)、裕必松(phosalone)、益滅松(phosmet)、福賜米松(phosphamidon)、巴賽松(phoxim)、亞特松(pirimiphos)-甲酯、佈飛松(profenofos)、撲達松(propetamphos)、普硫松(prothiofos)、白克松(pyraclofos)、必芬松(pyridaphenthion)、拜裕松(quinalphos)、硫帖(sulfotep)、得寧松(tebupirimifos)、得美松(temephos)、託福松(terbufos)、樂本松(tetrachlorvinphos)、硫滅松(thiometon)、三落松(triazophos)、三氯松(trichlorfon)和繁米松(vamidothion)。
(2)GABA-門控之氯化物通道阻斷劑,例如環二烯有機氯,例如克氯丹(chlordane)和安殺番(endosulfan);或苯基吡唑(fiprole),例如愛殺普洛(ethiprole)和芬普尼(fipronil)。
(3)鈉通道調節劑,例如擬除蟲菊酯,例如阿納寧(aerinathrin)、丙烯菊酯(allethrin)、d-順式-反式丙烯菊酯(allethrin)、d-反式丙烯菊酯(allethrin)、畢芬寧(bifenthrin)、右亞列寧(bioallethrin)、右亞列寧(bioallethrin)S-環戊烯基異構物、必賽靈(bioresmethrin)、乙氰菊酯(cycloprothrin)、賽扶寧(cyfluthrin)、β-賽扶寧、賽洛寧(cyhalothrin)、λ-賽洛寧、γ-賽洛寧、賽滅寧(cypermethrin)、α-賽滅寧、β-賽滅寧、θ-賽滅寧、ζ-賽滅寧、賽芬寧(cyphenothrin)[(1R)-反式異構物]、第滅寧(deltamethrin)、依普靈(empenthrin)[(EZ)-(1R)異構物]、益化利(esfenvalerate)、依芬寧(etofenprox)、芬普寧(fenpropathrin)、芬化利(fenvalerate)、福本賽寧(flucythrinate)、伏滅寧(flumethrin)、τ-福化利(fluvalinate)、海本斯(halfenprox)、益普靈(imiprothrin)、剋特寧(kadethrin)、(mom氯thrin)、百滅寧(permethrin)、芬特寧(phenothrin)[(1R)-反式異構物]、普烈靈(prallethrin)、除蟲菊酯(pyrethrins(pyrethrum))、利滅靈(resmethrin)、希拉芬(silafluofen)、特伏靈(tefluthrin)、特滅靈(tetramethrin)、特滅靈(tetramethrin)[(1R)異構物)]、泰滅 寧(tralomethrin)和參伏靈(transfluthrin);或DDT;或美克氯(methoxychlor)。
(4)菸鹼能乙醯膽鹼受體(nAChR)競爭調節劑,例如類新菸鹼類,例如乙醯普(acetamiprid)、克利定(clothianidin)、第諾芬(dinotefuran)、益達胺(imidacloprid)、尼普爛(nitenpyram)、硫克比(thiacloprid)和賽速安(thiamethoxam);或尼古丁;或碸蟲錠(sulfoxaflor);或福白二福隆(flupyradifurone)。
(5)菸鹼能乙醯膽鹼受體(nAChR)異位作用調節劑,例如賜諾殺類(Spinosyns),例如賜諾特(spinetoram)和賜諾殺(spinosad)。
(6)麩胺酸門控之氯化物通道(GluCl)異位作用調節劑,例如亞滅汀類(avermectins)/米貝黴素類(milbemycins),例如阿巴汀(abamectin)、因滅汀苯甲酸鹽(emamectin benzoate)、勒匹汀(lepimectin)和密貝汀(milbemectin)。
(7)幼保激素模擬物,例如幼保激素類似物,例如赫普靈(hydroprene)、克普靈(kinoprene)和滅普靈(methoprene);或吩克卡(fenoxycarb);或必普芬(pyriproxyfen)。
(8)混雜的非特異性(多位置)抑制劑,例如烷基鹵化物,例如甲基溴化物和其他的烷基鹵化物;或氯化苦(氯picrin)或硫醯氟(sulphuryl fluoride)或硼砂(borax)或吐酒石(tartar emetic)或異氰酸甲酯產生劑,例如敵柔米(diazomet)和威百畝(metam)。
(9)弦音器(Chordotonal organ)調節劑,例如必滅辛(pymetrozine);或伏卡滅(flonicamid)。
(10)蟎生長抑制劑,例如克芬辛(clofentezine)、海賽唑(hexythiazox)和地伏辛(diflovidazin);或抑特唑(etoxazole)。
(11)昆蟲腸膜之微生物幹擾劑,例如蘇雲金芽胞桿菌以色列亞種(Bacillus thuringiensis subspecies israelensis)、球形芽孢桿菌(Bacillus sphaericus)、蘇雲金芽胞桿菌鮎澤亞種(Bacillus thuringiensis subspecies aizawai)、蘇雲金芽胞桿菌庫斯塔基亞種(Bacillus thuringiensis subspecies kurstaki)、蘇雲金芽胞桿菌殺蟲亞種(Bacillus thuringiensis subspecies tenebrionis)和B.t.植物蛋白質Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、VIP3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/35Ab1。
(12)粒腺體ATP合成酶抑制劑,諸如ATP幹擾劑,例如地芬能(diafenthiuron);或有機錫化合物,例如亞賽錫(azocyclotin)、賽赫錫(cyhexatin)和芬塔錫(fenbutatin)氧化物;或歐蟎多(propargite);或特達芬(tetradifon)。
(13)經由幹擾質子梯度之氧化性磷酸化去偶合劑,例如克芬吡(chlorfenapyr)、DNOC和氟蟲胺(sulfluramid)。
(14)菸鹼能乙醯膽鹼受體通道阻斷劑,例如本速達(bensultap)、培丹(cartap)鹽酸鹽、硫克蘭(thiocylam)和硫速伏(thiosultap)-鈉。
(15)幾丁質生物合成抑制劑,第0型,例如必賽伏(bistrifluron)、克伏能(chlofluazuron)、地伏能(diflubenzuron)、伏賽能福環脲(flucycloxuron)、氟芬隆(flufenoxuron)、赫姆能(hexaflumuron)、利芬能(lufenuron)、利化能(novaluron)、諾化能(noviflumuron)、特速能(teflubenzuron)和三伏能(triflumuron)。
(16)幾丁質生合成抑制劑,第1型,例如佈芬辛(buprofezin)。
(17)蛻皮幹擾劑(尤其在雙翅目的例子中),例如賽滅淨(cyromazine)。
(18)脫皮激素受體促效劑,例如可芬諾(chromafenozide)、赫芬賽(halofenozide)、甲氧芬賽(methoxyfenozide)和特芬賽(tebufenozide)。
(19)章魚胺能受體促效劑,諸如三亞蟎(amitraz)。
(20)粒腺體複合物III電子傳輸抑制劑,諸如海滅能(hydra甲基none)或亞克希(acequinocyl)或伏克靈(fluacrypyrim)。
(21)粒腺體複合物I電子傳輸抑制劑,例如METI殺蟎劑,例如芬殺蟎(fenazaquin)、芬普蟎(fenpyroximate)、普靈芬(pyrimidifen)、畢達本(pyridaben)、達芬必(tebufenpyrad)和特芬必(tolfenpyrad)或魚藤精(rotenone)(Derris)。
(22)電壓依賴性鈉通道阻斷劑,例如因得克(indoxacarb)或美氟腙(metaflumizone)。
(23)乙醯基-Co-A羧酸酶抑制劑,例如特春酸(tetronic acid)和四聚酸(tetramic acid)衍生物,例如螺克芬(spirodiclofen)、螺滅芬(spiromesifen)和賜派滅(spirotetramat)。
(24)粒腺體複合物IV電子傳輸抑制劑,例如膦,例如磷化鋁、磷化鈣、膦和磷化鋅;或氰化物類,氰化鈣、氰化鉀和氰化鈉。
(25)粒腺體複合物II電子傳輸抑制劑,例如β-酮腈衍生物,例如氰必吩(cyenopyrafen)和賽福芬(cyflumetofen),及羧醯替苯胺,例如派福佈邁(pyflubumide)。
(28)理安諾鹼(Ryanodine)受體調節劑,例如二醯胺,例如剋安勃(chlorantraniliprole)、賽安勃(cyantraniliprole)和氟苯二醯胺(flubendiamide),更多的活性化合物,例如安伏滅(amidoflumet)、安伏索拉(afoxolaner)、查得定(azadirachtin)、苯克賽(benclothiaz)、苯賽滅(benzoximate)、必芬賽(bifenazate)、(broflanilide)、新殺蟎(溴propylate)、蟎離丹(chinomethionat)、氯丙炔菊酯(氯prallethrin)、克利得(cryolite)、賽拉尼波(cyclaniliprole)、環氧蟲啶(cycloxaprid)、氯氟氰蟲醯胺(cyhalodiamide)、狄可米柔泰茲(dicloromezotiaz)、大克蟎(dicofol)、ε-甲氧苄氟菊酯(epsilon metofluthrin)、ε-莫弗洛寧(epsilon momfluthrin)、氟托奎(flometoquin)、氟劄因朵辛(fluazaindolizine)、氟速吩(fluensulfone)、伏吩靈(flufenerim)、氟芬史托賓(flufenoxystrobin)、丁烯氟蟲腈(flufiprole)、氟殺逢(fluhexafon)、氟吡菌醯胺(fluopyram)、氟拉蘭(fluralaner)、氟米塔麥(fluxametamide)、呋喃蟲醯肼(fufenozide)、戊吡蟲胍(guadipyr)、害塔氟靈(heptafluthrin)、氯噻啉(imidaclothiz)、依普同(iprodione)、κ-畢芬寧(kappa bifenthrin)、κ-特伏靈(kappa tefluthrin)、羅提蘭(lotilaner)、氯氟醚菊酯(meperfluthrin)、呱蟲啶(paichongding)、必達利(pyridalyl)、必伏松(pyrifluquinazon)、嘧蟎胺(pyr亞 胺基strobin)、螺蟎雙酯(spirobudiclofen)、四氟醚菊酯(tetra甲基fluthrin)、四安利普(tetraniliprole)、四氯安利普(tetrachlorantraniliprole)、提芬(tioxazafen)、硫氟肟醚(Thiofluoximate)、三氟米比瑞(triflumezopyrim)和碘甲烷;另外以芽孢堅強桿菌(Bacillus firmus)(I-1582,BioNeem,Votivo)為主之製劑,及下列化合物:1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(自WO2006/043635已知)(CAS 885026-50-6)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚--3,4'-呱啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(自WO2003/106457已知)(CAS 637360-23-7)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]呱啶-4-基}-4-(三氟甲基)苯基]異菸鹼醯胺(自WO2006/003494已知)(CAS 872999-66-1)、3-(4-氯-2,6-二甲基苯基)-4-羥基-8-甲氧基-1,8-二氮雜螺[4.5]癸-3-烯-2-酮(自WO 2010052161已知)(CAS 1225292-17-0)、碳酸3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-側氧基-1,8-二氮雜螺[4.5]癸-3-烯-4-基乙酯(自EP 2647626已知)(CAS-1440516-42-6)、4-(丁-2-炔-1-氧基)-6-(3,5-二甲基呱啶-1-基)-5-氟嘧啶(自WO2004/099160已知)(CAS 792914-58-0)、PF1364(自JP2010/018586已知)(CAS登錄號1204776-60-2)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]亞吡啶-2(1H)-基]-2,2,2-三氟乙醯胺(自WO2012/029672已知)(CAS 1363400-41-2)、(3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-亞吡啶基]-1,1,1-三氟丙-2-酮(自WO2013/144213已知)(CAS 1461743-15-6)、N-[3-(苯甲基胺甲醯基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H-吡唑-5-羧醯胺(自WO2010/051926已知)(CAS 1226889-14-0)、5-溴-4-氯-N-[4-氯-2-甲基-6-(甲基胺甲醯基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-羧醯胺(自CN103232431已知)(CAS 1449220-44-3)、4-[5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異唑基]-2-甲基-N-(順式-1-氧撐-3-噻丁環基)苯甲醯胺、4-[5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異唑基]-2-甲基-N-(反式-1-氧撐-3-噻丁環基)苯甲醯胺和4-[(5S)-5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異唑基]-2- 甲基-N-(順式-1-氧撐-3-噻丁環基)苯甲醯胺(自WO 2013/050317 A1已知)(CAS 1332628-83-7)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]丙醯胺、(+)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]丙醯胺和(-)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]丙醯胺(自WO 2013/162715 A2、WO 2013/162716 A2、US 2014/0213448 A1已知)(CAS 1477923-37-7)、5-[[(2E)-3-氯-2-丙烯-1-基]胺基]-1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(三氟甲基)亞磺醯基]-1H-吡唑-3-甲腈(自CN 101337937 A已知)(CAS 1105672-77-2)、3-溴-N-[4-氯-2-甲基-6-[(甲基胺基)側硫甲基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-羧醯胺(liudaibenjiaxuanan,自CN 103109816 A已知)(CAS 1232543-85-9)、N-[4-氯-2-[[(1,1-二甲基乙基)胺基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-(氟甲氧基)-1H-吡唑-5-羧醯胺(自WO 2012/034403 A1已知)(CAS 1268277-22-0)、N-[2-(5-胺基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-羧醯胺(自WO 2011/085575 A1已知)(CAS 1233882-22-8)、4-[3-[2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基]丙氧基]-2-甲氧基-6-(三氟甲基)嘧啶(自CN 101337940 A已知)(CAS 1108184-52-6)、(2E)-和2(Z)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亞乙基]-N-[4-(二氟甲氧基)苯基]肼羧醯胺(自CN 101715774 A已知)(CAS 1232543-85-9)、環丙烷羧酸3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H-苯並咪唑-2-基)苯酯(自CN 103524422 A已知)(CAS 1542271-46-4)、(4aS)-7-氯-2,5-二氫-2-[[(甲氧基羰基)[4-[(三氟甲基)硫基]苯基]胺基]羰基]茚並[1,2-e][1,3,4]二-4a(3H)-羧酸甲酯(自CN 102391261 A已知)(CAS 1370358-69-2)、6-去氧-3-O-乙基-2,4-二-O-甲基-1-[N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1H-1,2,4-三唑-3-基]苯基]胺甲酸酯]-α-L-吡喃甘露糖(自US 2014/0275503 A1已知)(CAS 1181213-14-8)、8-(2-環丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基嗒-3-基)-3-氮雜雙環[3.2.1]辛烷(CAS 1253850-56-4)、(8-反)-8-(2-環丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基嗒-3-基)-3-氮雜雙環[3.2.1]辛烷(CAS 933798-27-7)、(8-順)-8-(2-環丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基嗒-3-基)-3-氮雜雙環[3.2.1]辛烷(自WO 2007040280 A1、WO 2007040282 A1已知)(CAS 934001-66-8)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫基]丙醯胺(自WO 2015/058021 A1、WO 2015/058028 A1已知)(CAS 1477919-27-9)及N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide N-[4-(胺基硫代甲基)-2-甲基-6-[(甲基胺基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(由CN 103265527 A得知)(CAS 1452877-50-7)。
在此以彼等的通用名稱具體指定之活性化合物為已知且說明於例如「殺蟲劑手冊」中(16th Ed.,British Crop Protection Council 2012)或於網路上可搜尋(例如http://www.alanwood.net/pesticides)。
在類別(1)至(15)中所述及之所有混合組份可視情況與適合的鹼或酸形成鹽,假設彼等係基於彼等的官能基而能夠因此達成以類別(1)至(15)中所述及之所有殺真菌混合組份可視情況包括互變異構物形式。
1)麥角固醇生物合成抑制劑,例如(1.001)西普康唑(cyproconazole)、(1.002)地吩康唑(difenoconazole)、(1.003)環氧克唑(epoxiconazole)、(1.004)吩醯胺(fenhexamide)、(1.005)芬普定(fenpropidin)、(1.006)芬普福(fenpropimorph)、(1.007)吩普胺(fenpyrazamine)、(1.008)伏克康唑(fluquinconazole)、(1.009)護汰芬(flutriafol)、(1.010)依滅列(imazalil)、(1.011)依滅列硫酸鹽(imazalil sulphate)、(1.012)抑普康唑(ipconazole)、(1.013)滅康唑(metconazole)、(1.014)麥克坦尼(myclobutanil)、(1.015)巴克素(paclobutrazole)、(1.016)撲克樂(prochloraze)、(1.017)普克利(propiconazole)、 (1.018)普賽康唑(prothioconazole)、(1.019)派異唑(Pyrisoxazole)、(1.020)賜必安(spiroxamine)、(1.021)得克利(tebuconazole)、(1.022)特康唑(tetraconazole)、(1.023)三泰隆(triadimenole)、(1.024)賽得莫(tridemorph)、(1.025)三狄康唑(triticonazole)、(1.026)(1R,2S,5S)-5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.027)(1S,2R,5R)-5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.028)(2R)-2-(1-氯環丙基)-4-[(1R)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.029)(2R)-2-(1-氯環丙基)-4-[(1S)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.030)(2R)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.031)(2S)-2-(1-氯環丙基)-4-[(1R)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.032)(2S)-2-(1-氯環丙基)-4-[(1S)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.033)(2S)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.034)(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲-醇、(1.035)(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲醇、(1.036)[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲醇、(1.037)1-({(2R,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧雜環戊烷-2-基}甲基)-1H-1,2,4-三唑、(1.038)1-({(2S,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧雜環戊烷-2-基}甲基)-1H-1,2,4-三唑、(1.039)硫代氰酸1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-酯、(1.040)硫代氰酸1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-酯、(1.041)硫代氰酸1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-酯、(1.042)2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.043)2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.044)2-[(2R,4S,5R)-1-(2,4- 二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.045)2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.046)2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.047)2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.048)2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.049)2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.050)2-[1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.051)2-[2-氯-4-(2,4-二氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.052)2-[2-氯-4-(4-氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.053)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.054)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)戊-2-醇、(1.055)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.056)2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.057)2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.058)2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.059)5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.060)5-(烯丙基硫基)-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.061)5-(烯丙基硫基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.062)5-(烯丙基硫基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)環氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.063)N'-(2,5-二甲基-4-{[3-(1,1,2,2-四氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.064)N'-(2,5-二甲基-4-{[3-(2,2,2-三氟乙氧基)苯基]硫基}苯基)-N- 乙基-N-甲基醯亞胺基甲醯胺、(1.065)N'-(2,5-二甲基-4-{[3-(2,2,3,3-四氟丙氧基)苯基]硫基}苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.066)N'-(2,5-二甲基-4-{[3-(五氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.067)N'-(2,5-二甲基-4-{3-[(1,1,2,2-四氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.068)N'-(2,5-二甲基-4-{3-[(2,2,2-三氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.069)N'-(2,5-二甲基-4-{3-[(2,2,3,3-四氟丙基)硫基]苯氧基}苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.070)N'-(2,5-二甲基-4-{3-[(五氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.071)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.072)N'-(4-{[3-(二氟甲氧基)苯基]硫基}-2,5-二甲基苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.073)N'-(4-{3-[(二氟甲基)硫基]苯氧基}-2,5-二甲基苯基)-N-乙基-N-甲基醯亞胺基甲醯胺、(1.074)N'-[5-溴-6-(2,3-二氫-1H-茚-2-氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基醯亞胺基甲醯胺、(1.075)N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基醯亞胺基甲醯胺、(1.076)N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基醯亞胺基甲醯胺、(1.077)N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基醯亞胺基甲醯胺、(1.078)N'-{5-溴-6-[(順式-4-異丙基環己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基醯亞胺基甲醯胺、(1.079)N'-{5-溴-6-[(反式-4-異丙基環己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基醯亞胺基甲醯胺、(1.080)N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基醯亞胺基甲醯胺、(1.081)氯氟醚菌唑(mefentrifluconazole)、(1.082)ipfentrifluconazole。
2)在複合物I或II上的呼吸鏈抑制劑,例如(2.001)苯丙烯氟菌唑(benzovindiflupyr)、(2.002)必賽吩(bixafen)、(2.003)保卡利(boscalid)、(2.004)卡布辛(carboxin)、(2.005)護派楠(fluopyram)、(2.006)護坦尼(flutolanil)、 (2.007)護賽保(fluxapyroxad)、(2.008)福滅普(furametpyr)、(2.009)艾索非他滅(Isofetamid)、(2.010)抑本散(isopyrazam)(反-差向異構體鏡像異構物1R,4S,9S)、(2.011)抑本散(反-差向異構體鏡像異構物1S,4R,9R)、(2.012)抑本散(反-差向異構體消旋物1RS,4SR,9SR)、(2.013)抑本散(順-差向異構體消旋物1RS,4SR,9RS與反-差向異構體消旋物1RS,4SR,9SR之混合物)、(2.014)抑本散(順-差向異構體鏡像異構物1R,4S,9R)、(2.015)抑本散(順-差向異構體鏡像異構物1S,4R,9S)、(2.016)抑本散(順-差向異構體消旋物1RS,4SR,9RS)、(2.017)本福吩(penflufen)、(2.018)本賽能(penthiopyrad)、(2.019)氟唑菌醯羥胺(pydiflumetofen)、(2.020)吡福敏(pyraziflumid)、(2.021)速達散(sedaxane)、(2.022)1,3-二甲基-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)-1H-吡唑-4-羧醯胺、(2.023)1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-羧醯胺、(2.024)1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-羧醯胺、(2.025)1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)聯苯基-2-基]-1H-吡唑-4-羧醯胺、(2.026)2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)苯甲醯胺、(2.027)3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)-1H-吡唑-4-羧醯胺、(2.028)3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-羧醯胺、(2.029)3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-羧醯胺、(2.030)3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-2,3-二氫-1H-茚-4-基)-1-甲基-1H-吡唑-4-羧醯胺、(2.031)3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1-甲基-1H-吡唑-4-羧醯胺、(2.032)3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1-甲基-1H-吡唑-4-羧醯胺、(2.033)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.034)N-(2-環戊基-5-氟苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.035)N-(2-第三丁基-5-甲基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.036)N-(2-第 三丁基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.037)N-(5-氯-2-乙基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.038)N-(5-氯-2-異丙基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.039)N-[(1R,4S)-9-(二氯亞甲基)-1,2,3,4-四氫-1,4-甲橋萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-羧醯胺、(2.040)N-[(1S,4R)-9-(二氯亞甲基)-1,2,3,4-四氫-1,4-甲橋萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-羧醯胺、(2.041)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-羧醯胺、(2.042)N-[2-氯-6-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.043)N-[3-氯-2-氟-6-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.044)N-[5-氯-2-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.045)N-環丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苯甲基]-1H-吡唑-4-羧醯胺、(2.046)N-環丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-異丙基苯甲基)-1-甲基-1H-吡唑-4-羧醯胺、(2.047)N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基-5-甲基苯甲基)-1-甲基-1H-吡唑-4-羧醯胺、(2.048)N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基苯甲基)-1-甲基-1H-吡唑-4-硫代甲醯胺、(2.049)N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基苯甲基)-1-甲基-1H-吡唑-4-羧醯胺、(2.050)N-環丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-異丙基苯甲基)-1-甲基-1H-吡唑-4-羧醯胺、(2.051)N-環丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲基苯甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.052)N-環丙基-3-(二氟甲基)-N-(2-乙基-5-氟苯甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.053)N-環丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苯甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.054)N-環丙基-N-(2-環丙基-5-氟苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.055)N-環丙基-N-(2-環丙基-5-甲基苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺、(2.056)N-環丙基-N-(2-環丙基苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧醯胺。
3)在複合物III上的呼吸鏈抑制劑,例如(3.001)辛唑嘧菌胺(ametoctradin)、(3.002)安美速(amisulbrom)、(3.003)亞托敏(azoxystrobin)、(3.004)甲香菌酯(coumethoxystrobin)、(3.005)丁香菌酯(coumoxystrobin)、(3.006)賽發滅(cyazofamid)、(3.007)醚菌胺(dimoxystrobin)、(3.008)烯肟菌酯(enoxastroburin)、(3.009)芬色丹(famoxadon)、(3.010)芬滅酮(fenamidone)、(3.011)伏芬氧賓(flufenoxystrobin)、(3.012)氟嘧菌酯(fluoxastrobin)、(3.013))克收欣(kresoxim-methyl)、(3.014)苯氧菌胺(metominostrobin)、(3.015)肟醚菌胺(orysastrobin)、(3.016)啶氧菌酯(picoxystrobin)、(3.017)唑菌胺酯(pyraclostrobin)、(3.018)唑胺菌酯(pyrametostrobin)、(3.019)唑菌酯(pyraoxystrobin)、(3.020)三氟敏(trifloxystrobin)、(3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基)苯基)亞乙基]胺基}氧基)甲基]苯基}-2-(甲氧基亞胺基)-N-甲基乙醯胺、(3.022)(2E,3Z)-5-{[1-(4-氯苯基)-1H-吡唑-3-基]氧基)-2-(甲氧基亞胺基)-N,3-二甲基戊-3-烯醯胺、(3.023)(2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙醯胺、(3.024)(2S)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙醯胺、(3.025)2-甲基丙酸(3S,6S,7R,8R)-8-苯甲基-3-[({3-[(異丁醯氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)胺基]-6-甲基-4,9-二側氧基-1,5-二氧雜環己烷-7-酯、(3.026)2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙醯胺、(3.027)N-(3-乙基-3,5,5-三甲基環己基)-3-甲醯胺基-2-羥基苯甲醯胺、(3.028)(2E,3Z)-5-{[1-(4-氯-2-氟苯基)-1H-吡唑-3-基]氧基)-2-(甲氧基亞胺基)-N,3-二甲基戊-3-烯醯胺、(3.029){5-[3-(2,4-二甲基苯基)-1H-吡唑-1-基]-2-甲基芐基}胺基甲酸甲酯。
4)有絲分裂與細胞分化抑制劑,例如(4.001)卡苯辛(carbendazim)、(4.002)地吩卡(diethofencarb)、(4.003)噻唑菌胺(ethaboxam)、(4.004)氟吡菌胺(fluopicolid)、(4.005)賓克隆(pencycuron)、(4.006)腐絕(thiabendazole)、(4.007)甲基多保淨(thiophanate-甲基)、(4.008)索醯胺(zoxamide)、(4.009)3- 氯-4-(2,6-二氟苯基)-6-甲基-5-苯基嗒、(4.010)3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基嗒、(4.011)3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)嗒、(4.012)4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.013)4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.014)4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.015)4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.016)4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.017)4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.018)4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.019)4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.020)4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.021)4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.022)4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基嗒、(4.023)N-(2-溴-6-氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.024)N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.025)N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
5)具有多重位置活性能力之化合物,例如(5.001)波爾多(Bordeaux)混合物、(5.002)四氯丹(captafol)、(5.003)蓋普丹(captan)、(5.004)四氯異苯腈(chlorothalonil)、(5.005)氫氧化銅、(5.006)萘甲酸銅、(5.007)氧化銅、(5.008)氯氧化銅、(5.009)硫酸銅(+2)、(5.010)腈硫醌(dithianon)、(5.011)多寧(dodin)、(5.012)福爾培(folpet)、(5.013)錳粉克(mancozeb)、(5.014)錳乃浦(maneb)、(5.015)滅得賴(metiram)、(5.016)滅得賴鋅鹽、(5.017)快得寧(copper oxine)、(5.018)甲基鋅乃浦(propineb)、(5.019)硫與硫製劑,包括多硫化鈣、(5.020)得恩地(thiram)、(5.021)鋅乃浦(zineb)、(5.022)益穗(ziram)、(5.023)6-乙基-5,7-二側氧基-6,7-二氫-5H-吡咯並[3',4':5,6][1,4]二噻英(dithiino)[2,3-c][1,2]噻唑-3-腈。
6)能夠觸發宿主防禦之化合物,例如(6.001)阿昔苯拉(acibenzolar)-S-甲酯、(6.002)異噻菌胺(isotianil)、(6.003)撲殺熱(probenazole)、(6.004)地得尼(tiadinil)。
7)胺基酸及/或蛋白質生物合成抑制劑,例如(7.001)嘧菌環胺(cyprodinil)、(7.002)賜黴素(kasugamycin)、(7.003)賜黴素鹽酸鹽水合物、(7.004)土黴素(oxytctracycline)、(7.005)比坦尼(pyrimethanil)、(7.006)3-(5-氟-3,3,4,4-四甲基-3,4-二氫異喹啉-1-基)喹啉。
8)ATP生產抑制劑,例如(8.001)矽硫吩(silthiofam)。
9)細胞壁合成抑制劑,例如(9.001)苯賽卡(benthiavalicarb)、(9.002)地滅莫(dimethomorph)、(9.003)伏莫(flumorph)、(9.004)抑發利(iprovalicarb)、(9.005)曼普胺(mandipropamid)、(9.006)丁吡嗎啉(pyrimorph)、(9.007)發利列(valifenalate)、(9.008)(2E)-3-(4-第三丁基苯基)-3-(2-氯吡啶-4-基)-1-(嗎啉-4-基)丙-2-烯-1-酮、(9.009)(2Z)-3-(4-第三丁基苯基)-3-(2-氯吡啶-4-基)-1-(嗎啉-4-基)丙-2-烯-1-酮。
10)脂質及薄膜合成抑制劑,例如(10.001)普莫卡(propamocarb)、(10.002)普莫卡鹽酸鹽(propamocarb hydrochloride)、(10.003)特克斯-甲酯(tolclofos-methyl)。
11)黑色素生物合成抑制劑,例如(11.001)三賽唑(tricyclazole)、(11.002){3-甲基-1-[(4-甲基苯甲醯基)胺基]丁-2-基}胺甲酸2,2,2-三氟乙酯。
12)核酸合成抑制劑,例如(12.001)本達樂(benalaxyl)、(12.002)本達樂-M(克拉利(kiralaxyl))、(12.003)滅達樂(metalaxyl)、(12.004)滅達樂-M(滅芬散(mefenoxam))。
13)訊號轉導抑制劑,例如(13.001)護汰寧(fludioxonil)、(13.002)依普同(iprodione)、(13.003)撲滅寧(procymidone)、(13.004)丙氧喹啉(proquinazid)(13.005)快諾芬(quinoxyfen)、(13.006)免克寧(vinclozolin)。
14)可充當去偶合劑之化合物,例如(14.001)扶吉胺(fluazinam)、(14.002) 敵蟎普(meptyldinocap)。
15)更多的化合物,例如(15.001)脫落酸(abscisic acid)、(15.002)本塞唑(benthizole)、(15.003)苯噻金(bethoxazine)、(15.004)卡普黴素(capsimycin)、(15.005)卡吩(carvone)、(15.006)喹啉甲硫胺酸鹽(chinomethionate)、(15.007)庫發尼(cufraneb)、(15.008)賽伏醯胺(cyflufenamid)、(15.009)西莫尼(cymoxanil)、(15.010)賽芬胺(cyprosulfamide)、(15.011)噻菌淨(flutianil)、(15.012)福賽得鋁(fosetyl-aluminium)、(15.013)福賽得鈣、(15.014)福賽得鈉、(15.015)異硫代氰酸甲酯、(15.016)滅奇吩(metrafenone)、(15.017)米德黴素(mildiomycin)、(15.018)納坦黴素(natamycin)、(15.019)二甲基二硫代胺甲酸鎳、(15.020)硝基太(nitrothal)-異丙基、(15.021)歐賽保(oxamocarb)、(15.022)奧賽普林(oxathiapiproline)、(15.023)歐芬汀(oxyfenthiine)、(15.024)五氯酚及其鹽類、(15.025)磷酸及其鹽類、(15.026)霜黴威乙膦酸鹽(propamocarb-fosetylate)、(15.027)必芬酮(pyriofenone)(克雜芬酮(chlazafenon))、(15.028)美爾奎寧(tebufloquin)、(15.029)特克爛(tecloftalam)、(15.030)特伏尼(tolnifanid)、(15.031)1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氫-1,2-唑-3-基]-1,3-噻唑-2-基}呱啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.032)1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氫-1,2-唑-3-基]-1,3-噻唑-2-基}呱啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.033)2-(6-苯甲基吡啶-2-基)喹唑啉、(15.034)2,6-二甲基-1H,5H-[1,4]二硫並[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮、(15.035)2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-(丙-2-炔-1-氧基)苯基]-4,5-二氫-1,2-唑-3-基}-1,3-噻唑-2-基)呱啶-1-基]乙酮、(15.036)2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氯-6-(丙-2-炔-1-氧基)苯基]-4,5-二氫-1,2-唑-3-基}-1,3-噻唑-2-基)呱啶-1-基]乙酮、(15.037)2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氟-6-(丙-2-炔-1-氧基)苯基]-4,5-二氫-1,2-唑-3-基}-1,3-噻唑-2-基)呱啶-1-基]乙酮、(15.038)2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2- 基]喹唑啉、(15.039)甲烷磺酸2-{(5R)-3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}呱啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-唑-5-基}-3-氯苯酯、(15.040)甲烷磺酸2-{(5S)-3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}呱啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-唑-5-基}-3-氯苯酯、(15.041)2-{2-[(7,8-二氟-2-甲基喹啉-3-基)氧基]-6-氟苯基}丙-2-醇、(15.042)2-{2-氟-6-[(8-氟-2-甲基喹啉-3-基)氧基]苯基}丙-2-醇、(15.043)甲烷磺酸2-{3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}呱啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-唑-5-基}-3-氯苯酯、(15.044)甲烷磺酸2-{3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}呱啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-唑-5-基}苯酯、(15.045)2-苯基苯酚和鹽、(15.046)3-(4,4,5-三氟-3,3-二甲基-3,4-二氫異喹啉-1-基)喹啉、(15.047)3-(4,4-二氟-3,3-二甲基-3,4-二氫iso喹啉-1-基)喹啉、(15.048)4-胺基-5-氟嘧啶-2-醇(互變異構物形式:4-胺基-5-氟嘧啶-2(1H)-酮)、(15.049)4-側氧基-4-[(2-苯基乙基)胺基]丁酸、(15.050)5-胺基-1,3,4-噻二唑-2-硫醇、(15.051)5-氯N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-碸醯肼、(15.052)5-氟-2-[(4-氟苯甲基)氧基]嘧啶-4-胺、(15.053)5-氟-2-[(4-甲基苯甲基)氧基]嘧啶-4-胺、(15.054)9-氟-2,2-二甲基-5-(喹啉-3-基)-2,3-二氫-1,4-苯氧環氮己三烯、(15.055){6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亞甲基]胺基}氧基)甲基]吡啶-2-基}胺甲酸丁-3-炔-1-酯、(15.056)(2Z)-3-胺基-2-氰基-3-苯基丙烯酸乙酯、(15.057)啡-1-羧酸、(15.058)3,4,5-三羥基苯甲酸丙酯、(15.059)喹啉-8-醇、(15.060)喹啉-8-醇硫酸鹽(2:1)、(15.061){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亞甲基]胺基}氧基)甲基]吡啶-2-基}胺甲酸第三丁酯、(15.062)5-氟-4-亞胺基-3-甲基-1-[(4-甲基苯基)磺醯基]-3,4-二氫嘧啶-2(1H)-酮。
可將式(I)化合物與生物殺蟲劑組合。
生物殺蟲劑尤其包括細菌、真菌、酵母、植物萃取物及由微生物所形成的產物,包括蛋白質和二級代謝物。
生物殺蟲劑包括細菌,諸如孢子形成細菌、樹根選殖細菌及充當生物殺昆蟲劑、殺真菌劑或殺線蟲劑之細菌。
用作或可用作為生物殺蟲劑之此等細菌的實例為:液化澱粉芽孢桿菌(Bacillus amyloliquefaciens),菌株FZB42(DSM 231179)、或仙人掌桿菌(Bacillus cereus),尤其為仙人掌桿菌菌株CNCM I-1562、或堅強桿菌(Bacillus firmus),菌株I-1582(寄存編號CNCM I-1582)、或短小芽胞桿菌(Bacillus pumilus),尤其為菌株GB34(寄存編號ATCC 700814)和菌株QST2808(寄存編號NRRL B-30087)、或枯草芽孢桿菌(Bacillus subtilis),尤其為菌株GB03(寄存編號ATCC SD-1397)、或枯草芽孢桿菌菌株QST713(寄存編號NRRL B-21661)、或枯草芽孢桿菌菌株OST 30002(寄存編號NRRL B-50421)、或蘇雲金芽孢桿菌(Bacillus thuringiensis),尤其為蘇雲金芽孢桿菌以色列亞種(血清型H-14),菌株AM65-52(寄存編號ATCC 1276)、或蘇雲金芽孢桿菌亞華亞種(aizawai),尤其為菌株ABTS-1857(SD-1372)、或蘇雲金芽孢桿菌鮎澤亞種(kurstaki)菌株HD-1、或蘇雲金芽孢桿菌擬步行甲亞種(tenebrionis)菌株NB 176(SD-5428)、穿刺巴斯德桿菌(Pasteuria penetrans)、巴斯德桿菌屬(Pasteuria spp.)(腎形腎狀線蟲)-PR3(寄存編號ATCC SD-5834)、細黃鏈黴菌(Streptomyces microflavus)菌株AQ6121(=QRD 31.013,NRRL B-50550)、細黃鏈黴菌(Streptomyces galbus)菌株AQ 6047(寄存編號NRRL 30232)。
用作或可用作為生物殺蟲劑之真菌和酵母的實例為:白殭菌(Beauveria bassiana),特別為菌株ATCC 74040、微坦盾殼黴(Coniothyrium minitans),特別為菌株CON/M/91-8(寄存編號DSM-9660)、輪枝菌屬對(Lecanicillium spp.),特別為菌株HRO LEC 12、蠟蚧輪枝菌(Lecanicillium lecanii)(從前已知為臘蚧輪刺孢菌(Verticillium lecanii)),特別 為菌株KV01、黑殭菌(Metarhizium anisopliae),尤其為菌株F52(DSM3884/ATCC 90448)、核果梅奇酵母(Metschnikowia fructicola),尤其為菌株NRRL Y-30752、玫煙色擬青黴菌(Paecilomyces fumosoroseus)(現在:玫煙色擬青黴菌(Isaria fumosorosea)),尤其為菌株IFPC 200613或菌株Apopka 97(寄存編號ATCC 20874)、淡紫擬青黴菌(Paecilomyces lilacinus),尤其為淡紫擬青黴菌菌株251(AGAL 89/030550)、黃藍狀菌(Talaromyces flavus),尤其為菌株V117b、深綠木黴(Trichoderma atroviridc),尤其為菌株SC1(寄存編號CBS 122089)、木黴菌(Trichoderma harzianum),尤其為哈氏木黴菌(T.harzianum rifai)T39(寄存編號CNCM I-952)。
用作或可用作為生物殺蟲劑之病毒的實例為:蘋果小捲葉蛾(Adoxophyes orana)(夏季水果捲葉蛾(summer fruit tortrix))顆粒症病毒(GV)、蘋果蠹蛾(Cydia pomonella)(蘋果蠹蛾(codling moth))顆粒症病毒(GV)、番茄夜蛾(Helicoverpa armigera)(棉花暝蛉(cotton bollworm))核型多角體病毒(NPV)、甜菜夜蛾(Spodoptera exigua)(甜菜夜蛾(beet armyworm))mNPV、秋夜盜蛾(Spodoptera frugiperda)(秋夜盜蛾(fall armyworm))mNPV、非洲棉葉蟲蛾(Spodoptera littoralis)(非洲棉葉蟲蛾(African cotton leafworm))NPV。
亦包括作為「接種物」添加至植物或植物部份或植物組織且由於彼等特別的性質而促進植物生長及健康的細菌和真菌。實例包括:農桿菌屬(Agrobacterium spp.)、莖瘤固氮根瘤菌(Azorhizobium caulinodans)、固氮螺旋菌(Azospirillum spp.)、固氮菌屬(Azotobacter spp.)、慢生根瘤菌屬(Bradyrhizobium spp.)、伯克霍德氏菌(Burkholderia spp.),尤其為洋蔥假單胞菌(Burkholderia cepacia)(從前已知為蔥頭假單孢菌(Pseudomonas cepacia))、大孢子屬(Gigaspora spp.)或單孢巨孢囊黴(Gigaspora monosporum)、根繡球菌(Glomus spp.)、賭蘑屬(Laccaria spp,)、布赫內氏乳桿菌(Lactobacillus buchneri)、擬繡球菌屬(Paraglomus spp.)、豆包菌(Pisolithus tinctorus)、假單胞菌屬(Pseudomonas spp.)、根瘤菌屬(Rhizobium spp.),尤其為三葉草根瘤菌(Rhizobium trifolii)、鬚腹菌屬(Rhizopogon spp.)、硬皮馬勃菌(Scleroderma spp.)、乳牛肝菌屬(Suillus spp.)、鏈黴菌屬(Streptomyces spp)。
用作或可用作為生物殺蟲劑之植物萃取物及由微生物所形成之產物(包括蛋白質和二級代謝物)的實例為:大蒜種球(Allium sativum)、苦艾(Artemisia absinthium)、印楝素(azadirachtin)、Biokeeper WP、肉桂微黑(Cassia nigricans)、苦皮藤(Celastrus angulatus)、臭杏(Chenopodium anthelminticum)、甲殼素(chitin)、Armour-Zen、綿馬(Dryopteris filix-mas)、問荊草(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(藜麥皂素萃取物(Chenopodium quinoa saponin extract))、除蟲菊屬/除蟲菊酯(pyrethrum/pyrethrins)、可木(Quassia amara))、櫟樹屬(Quercus)、皂樹皮(Quillaja)、Regalia、〝RequiemTM殺昆蟲劑〞、毒魚藤素(rotenone)、魚尼丁/利阿諾定(ryania/ryanodine)、紫草葉(Symphytum officinale)、艾菊(Tanacetum vulgare)、百里酚、Triact 70、TriCon、金蓮花(Tropaeulum majus)、異株蕁麻(Urtica dioica)、藜蘆鹼(Veratrin)、槲寄生(Viscum album)、十字花科(Brassicaceae)萃取物,尤其為油菜粉或芥末粉。
式(I)化合物可與安全劑組合,例如解草酮(benoxacor)、解毒喹(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、賽磺醯胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole)(-ethyl)、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草唑(furilazole)、雙苯唑酸(isoxadifen)(-methyl)、吡唑解草酯(mefenpyr)(-diethyl)、萘酸酐、解草腈(oxabetrinil)、2-甲氧基-N-({4-[(甲基胺甲醯基)胺基]苯基}磺醯基)苯甲醯胺(CAS 129531-12-0)、4-(二氯乙醯基)-1-氧雜-4-氮雜螺[4.5]癸烷(CAS 71526-07-3)、2,2,5-三甲基-3-(二氯乙醯基)-1,3-唑啶(CAS 52836-31-4)。
整株植物和植物部份可依照本發明處理。應瞭解植物在此意指整株植物和植株部分,諸如所欲及非所欲野生植物或作物植物(包括天然生成作物植物),例如穀類(小麥、稻米、黑小麥、大麥、裸麥、燕麥)、玉米、大豆、馬鈴薯、甜菜、甘蔗、蕃茄、黃瓜、甜瓜、胡蘿蔔、西瓜、洋蔥、萵苣、菠菜、韭菜、豆子、甘藍(例如包心菜)和其他蔬菜種類、棉花、煙草、油菜,及亦為果實植物(果實為蘋果、梨、柑橘和葡萄藤)。作物植物可為藉由習知的育種及優化方法、或藉由生物科技和基因工程方法、或該等方法之組合而獲得的植物,包括基因轉殖植物及包括可受到或未受到品種產權(varietal property right)保護的植物變種。應瞭解植物意指所有的發展階段,諸如種子、幼苗、年輕(未成熟)植物到成熟植物。應瞭解植物部份意指植物在地上及地下的所有部份及組織,諸如苗芽、葉子、花和根,給出的實例為葉子、針、莖、幹、花、果實體、果實和種子,且亦為根、塊莖和根莖。植物部份亦包括收成之植物或收成之植物部份及生長和生殖播種原料,例如幼苗、塊莖、根莖、分株和種子。
以式(I)化合物處理植物和植物部份係以習知的本發明處理方法直接進行或容許化合物在其周圍、環境或貯藏空間作用,例如藉由浸漬、噴灑、蒸發、氣霧化、散播、塗覆、注射,及在播種原料的例子中,尤其在種子的例子中,亦藉由施予一或多層來進行。
如已於上文所述,有可能依照本發明處理整株植物和其部份。在較佳的實施態樣中,處理野生植物及植物栽培品種、或那些藉由習知的生物育種方法(諸如交配或原生質體融合)所獲得者,以及其部份。在更佳的實施態樣中,處理藉由基因工程方法(若適當時,與習知的方法組合)所獲得的基因轉殖植物及植物栽培品種(基因改造有機體),以及其部份。術語「部份」、「植物的部份」或「植物部份」已於上文解釋。依照本發明特別優先選擇處理 個別於市場上慣常的植物栽培品種或那些使用中的植物。應瞭解植物栽培品種意指具有新性質(「特質」)且已藉由習知的育種、藉由突變形成或藉由重組DNA技術而獲得的植物。該等可為栽培品種、變種、生物型或基因型。
欲依照本發明處理之較佳的基因轉殖植物或植物栽培品種(那些藉由基因工程所獲得者)包括所有的植物,其通過基因改造而接收賦予該等植物特別有利且有用的性質(「特質」)之基因原料。該等性質的實例為更好的植物生長、增加對高溫或低溫的耐受性、增加對乾旱或水或土壤鹽度水準的耐受性、提高開花性能、更容易收成、加速成熟、更高的產率、收成產品有更高的品質及/或更高的營養價值、更好的貯藏壽命及/或收成產品的可加工性。該等性質的更多且特別強調的實例為增加植物對抗動物和微生物害蟲之抗性,諸如對抗昆蟲、蜘蛛綱、線蟲、蟎、蛞蝓和蝸牛(由於例如在植物中所形成的毒素,特別為那些藉由來自蘇雲金芽孢桿菌的基因原料(例如藉由基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF,以及其組合)而於植物中所形成的毒素),及亦為增加植物對抗由例如整體所需抗性(SAR)、系統素、植物防禦素、激發子及抗性基因所引起的致植物病性真菌、細菌及/或病毒及對應表現之蛋白質和毒素之抗性,及亦為增加植物對特定的除草活性化合物之耐受性,例如咪唑啉酮、磺醯脲、草甘膦(glyphosate)或草胺磷(phosphinotricin)(例如「PAT」基因)。賦予討論中的所欲特質之基因亦可彼此組合存在於基因轉殖植物中。所述及之基因轉殖植物的實例包括重要的作物植物,諸如穀類(小麥、稻米、黑小麥、大麥、裸麥、燕麥)、玉米、大豆、馬鈴薯、甜菜、甘蔗、蕃茄、豌豆和其他蔬菜種類、棉花、煙草、油菜,及亦為果實植物(果實為蘋果、梨、柑橘和葡萄),特別強調玉米、大豆、小麥、稻米、馬鈴薯、棉花、甘蔗、煙草和油菜。特別強調的性質(「特質」)為增加植物對昆蟲、蜘 蛛綱、線蟲、蛞蝓和蝸牛之抗性。
植物和植物部份係使用習知的處理方法以式(I)化合物直接處理或藉由作用在其周圍、環境或貯藏空間來處理,例如藉由浸漬、噴灑、霧化、灌溉、蒸發、噴粉、氣霧化、撒佈、發泡、噴塗、散佈、注射、灑水(澆灌)、滴藥灌溉,及在播種原料的例子中,特別在種子的例子中,另外以乾式種子處理、液體種子處理、漿液處理、藉由包覆、藉由塗上一或多層等等。此外,有可能以超低容量法施予式(I)化合物,或以施予形式或式(I)化合物本身注入土壤中。
較佳的直接處理植物為施予樹葉,意指將式(I)化合物施予樹葉,其中處理頻率及施予率應根據討論中的害蟲侵襲程度來調整。
在全面性活性化合物的例子中,式(I)化合物係經由根系統進入植物。接著植物係藉由式(I)化合物作用於植物棲息處來處理。這可例如藉由澆灌或混合至土壤或營養液中而實現,意指將植物的所在地(例如土壤或水耕系統)以液體形式的式(I)化合物灌注,或藉由土壤施予而實現,意指將根據本發明呈固體形式(例如呈粒劑形式)的式(I)化合物引入植物所在地。在水稻作物的例子中,這可藉由計量供給呈固體施予形式(例如呈粒劑)的式(I)化合物至水稻田中而實現。
長期以來已知藉由處理植物種子來控制動物害蟲,且此控制為不斷改進的議題。然而,種子的處理引起一系列總是無法以令人滿意的方式解決之問題。因此,希望發展出在貯藏期間、在播種之後或在植物出苗之後免除或至少顯著地減少額外施予殺蟲劑以保護種子及發芽植物之方法。此外,希望所使用的活性化合物量最優化,以便提供種子及發芽植物最優化 保護而免於動物害蟲的感染,但是所使用的活性化合物不傷害植物本身。用於處理種子之方法亦應特別慮及抗害蟲性或耐害蟲性基因轉殖植物的固有殺昆蟲或殺線蟲性質,以便使用最少用量的殺蟲劑達成對種子及亦對發芽植物的最優化保護。
本發明因此亦特別關於保護種子及發芽植物免於害蟲感染之方法,其係藉由以式(I)化合物中之一者處理種子。用於保護種子及發芽植物免於害蟲感染之根據本發明的方法另外包含其中將種子以式(I)化合物及混合組份同時於一次操作中處理或相繼處理之方法。該方法亦另外包含其中將種子以式(I)化合物及混合組份於不同的時間處理之方法。
本發明同樣關於式(I)化合物處理種子以保護種子及所得植物免於動物害蟲之用途。
本發明另外關於已根據本發明的式(I)化合物處理而予以保護免於動物害蟲之種子。本發明亦關於同時以式(I)化合物及混合組份處理之種子。本發明另外關於在不同時間經式(I)化合物及混合組份處理之種子。在種子在不同時間經式(I)化合物及混合組份處理的例子中,個別物質可以不同的層存在於種子上。在此例子中,包含式(I)化合物及混合組份的層可選擇地以中間層分開。本發明亦關於其中已施予成為塗層的一部分或成為除了塗層以外的另一層或更多層的式(I)化合物及混合組份之種子。
本發明另外關於在以式(I)化合物處理之後進行包膜程式以防止在種子上的灰塵磨耗之種子。
在式(I)化合物以全面性作用時出現的優點之一為種子的處理不僅保護種子本身而已,且亦保護在出苗之後的所得植物免於動物害蟲。以此方式,可免除在播種時或隨後旋即對作物的立即處理。
另一優點為以式(I)化合物處理種子可提高經處理種子之發芽及出苗。
同樣視為優點的是式(I)化合物尤其亦可用於基因轉殖種子。
式(I)化合物亦可與傳訊技術之組成物或化合物組合使用,其導致共生 體(例如根瘤菌、菌根及/或內生性細菌或真菌)更好的選殖,及/或導致最優化固氮作用。
式(I)化合物適合於保護在農業、溫室、林業或園藝中使用的任何植物品種之種子。更特別為下列之種子:穀類(例如小麥、大麥、裸麥、小米和燕麥)、玉米、棉花、大豆、稻米、馬鈴薯、向日葵、咖啡、菸草、油菜花、油菜、甜菜(例如糖用甜菜和飼料甜菜)、花生、蔬菜(例如番茄、胡瓜、豆子、十字花科蔬菜、洋蔥和萵苣)、果實植物、草皮及觀賞植物。下列種子的處理具有特別的重要性:穀類(諸如小麥、大麥、裸麥和燕麥)、玉米、大豆、棉花、油菜籽、油菜、蔬菜和稻米。
如已於上文所述,以式(I)化合物處理基因轉殖種子亦具有特別的重要性。這包含通常含有至少一種控制特別具有殺昆蟲及/或殺線蟲性質的多肽表現之異源性基因的植物種子。在基因轉殖種子中的異源性基因可源自微生物,諸如桿菌(Bacillus)、根瘤菌(Rhizobium)、假單胞菌(Pseudomonas)、沙雷氏菌(Serratia)、木黴菌(Trichoderma)、棒狀桿菌(Clavibacter)、菌根菌(Glomus)或膠狀青黴菌(Gliocladium)。本發明特別適合於處理包含至少一種源自桿菌屬的異源基因之基因轉殖種子。以衍生自蘇雲金芽胞桿菌(Bacillus thuringiensis)的異源性基因更佳。
在本發明的上下文中,式(I)化合物係施予種子。較佳地處理在處理期間呈足以避免傷害的穩定狀態之處子。通常可在收成與播種之間的任何時間點處理種子。按慣例使用已與植物分離且沒有穗軸、外殼、莖、表皮、毛或果肉之種子。例如,有可能使用已收成、清洗且乾燥至容許貯藏的水分含量之種子。另一選擇地,亦有可能使用在乾燥之後已經例如水處理且接著再乾燥(例如蒸濺)之種子。在稻米種子的例子中,亦有可能使用已在例如水中預膨脹直到其到達稻米胚芽之特定階段(雞胸期(pigeon breast stage))之種子,其導致刺激發芽及更均勻的出苗。
當處理種子時,通常必須仔細選擇施予種子的式(I)化合物量及/或其他 的添加劑量,以此方式對種子發芽沒有不利的影響,或不傷害所得植物。在特定的施予率下可展現植物毒性效應之活性化合物的例子中,必須特別確保如此。
式(I)化合物通常係以適合的調配物形式施予種子。適合於種子處理之調配物及方法為熟習本技術領域者已知。
式(I)化合物可轉化成習知的種子敷料調配物,諸如溶液、乳液、懸浮液、粉劑、泡沫、漿液或用於種子的其他包膜組成物,且亦為ULV調配物。
該等調配物係藉由將式(I)化合物與習知的添加劑混合的已知方式製得,例如與習知的增量劑及溶劑或稀釋劑、染料、潤濕劑、分散劑、乳化劑、消泡劑、防腐劑、二次增稠劑、黏著劑、赤黴素及亦與水混合。
可存在於可依照本發明使用的種子敷料調配物中的適當染料為出於此等目的而習知的所有染料。有可能使用難溶於水中的顏料或可溶於水中的染料。實例包括以若丹明(Rhodamin)B、C.I.紅色顏料112號和C.I.紅色溶劑1號為名稱的已知染料。
可存在於依照本發明使用的種子敷料調配物中有用的潤濕劑為促進潤濕且習知用於農化活性化合物之調配物的所有物質。優先選擇使用萘磺酸烷酯,諸如萘磺酸二異丙酯-或二異丁酯。
可存在於依照本發明使用的種子敷料調配物中適合的分散劑及/或乳化劑為習知用於農化活性化合物之調配物的所有非離子、陰離子和陽離子分散劑。可優先選擇使用非離子或陰離子分散劑或非離子或陰離子分散劑之混合物。適合的非離子分散劑尤其包括環氧乙烷/環氧丙烷嵌段聚合物、烷基苯酚聚乙二醇醚和三苯乙烯基苯酚聚乙二醇醚、及其磷酸化或硫酸化衍生物。適合的陰離子分散劑尤其為木質磺酸鹽、聚丙烯酸鹽和芳基磺酸鹽/甲醛縮合物。
可存在於依照本發明使用的種子敷料調配物中的消泡劑為習知用於農化活性化合物之調配物的所有泡沫抑制物質。可優先使用聚矽氧消泡劑和 硬脂酸鎂。
可存在於依照本發明使用的種子敷料調配物中的防腐劑為出於此等目的而用於農化組成物中的所有物質。實例包括二氯吩和苯甲醇半縮甲醛。
可存在於依照本發明使用的種子敷料調配物中的有用的二次增稠劑為出於此等目的而用於農化組成物中的所有物質。較佳的實例包括纖維素衍生物、丙烯酸衍生物、黃原膠、經改質之黏土和細碎矽石。
可存在於依照本發明使用的膠黏劑為可用於種子敷料產品中的所有習知的結合劑。較佳的實例包括聚乙烯基吡咯啶酮、聚乙酸乙烯酯、聚乙烯醇和甲基纖維素(tylose)。
可存在於依照本發明使用的種子敷料調配物中的有用的赤黴素較佳為赤黴素A1、A3(=赤黴酸)、A4和A7;特別優先選擇使用赤黴酸。赤黴素為已知的化合物(參考R.Wegler "Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel",vol.2,Springer Verlag,1970,pp.401-412)。
依照本發明使用的種子敷料調配物可直接或事先以水稀釋之後用於處理各種廣泛不同種類的種子。例如,濃縮物或自其以水稀釋可獲得的製劑可用於塗敷下列種子:穀類(諸如小麥、大麥、黑麥、燕麥和黑小麥),以及玉米、稻米、油菜、豌豆、豆子、棉花、向日癸、大豆和甜菜的種子,或其他各種廣泛不同種類的蔬菜種子。依照本發明使用的種子敷料調配物或其稀釋的應用型式亦可用於塗敷基因轉殖植物之種子。
依照本發明使用的種子敷料調配物或通過添加水而自其製備的應用型式處理種子時,可使用習知用於種子塗敷的所有混合單元。特定言之,種子塗敷程式係將種子分批或以連續操作放入混合器中,添加特定的所欲量之種子敷料調配物(以其原樣子或事先以水稀釋之後)且混合,直到調配物均勻地分佈於種子上為止。若適當時,隨後進行乾燥操作。
依照本發明使用的種子敷料調配物之施予率可在相當寬廣的範圍內改變。施予率係以調配物中的式(I)化合物之特定含量及種子所支配。式(I)化 合物之施予率通常係介於以每公斤種子計0.001與50克之間,較佳為介於以每公斤種子計0.01與15克之間。
在動物健康領域中,亦即在獸醫用藥領域中,式(I)化合物具有對抗動物寄生蟲的活性,特別為體外寄生蟲或體內寄生蟲。術語「體內寄生蟲」尤其包括蠕蟲和原生動物,諸如球蟲(coccidia)。體外寄生蟲通常且較佳為節肢動物,尤其為昆蟲和蟎。
在獸醫用藥領域中,具有利的溫血毒性之式(I)化合物適合於控制出現在畜牧動物和家畜動物、育種動物、動物園動物、實驗室動物和家養動物中的寄生蟲。該等化合物具有對抗所有或特定發展階段之寄生蟲的活性。
農業牲畜包括例如哺乳動物,諸如綿羊、山羊、馬、驢、駱駝、水牛、兔子、馴鹿、扁角鹿(fallow deers),且尤其為牛和豬;或家禽,諸如火雞、鴨、鵝,且尤其為雞;魚和例如水產養殖之甲殼類動物;或視情況可為昆蟲,諸如蜜蜂。
家養動物包括例如哺乳動物,諸如倉鼠、天竺鼠、大鼠、小鼠、南美栗鼠、雪貂,且特別為狗、貓、籠養鳥類;爬蟲、兩棲類動物和觀賞魚類。
在特定的實施態樣中,將式(I)化合物投予哺乳動物。
在另一特定的實施態樣中,將式(I)化合物投予鳥類,亦即籠養鳥類,且特別為家禽。
意欲使用控制動物寄生蟲的式(I)化合物減少或預防疾病、死亡個案和性能降低(在肉、奶、毛、皮、蛋、蜂蜜和類似者的例子中),使得能夠更經濟及更簡單的動物飼養,且可達成更好的動物福祉。
在本發明的上下文中,關於動物健康領域之術語「控制(control)」或「控制(controlling)」意指式(I)化合物有效使以此等寄生蟲感染之動物中的特定寄生蟲之發生率減少至無害的程度。更特定言之,在本發明的上下文中的 「控制(control)」意指式(I)化合物殺死個別的寄生蟲、抑制其生長或抑制其繁殖。
節肢動物包括例如但不限於:來自蝨目(Anoplurida),例如血蝨屬(Haematopinus spp.)、毛蝨屬(Linognathus spp.)、蝨屬(Pediculus spp.)、陰蝨屬(Phtirus spp.)和牛蝨屬(Solenopotes spp.);來自食毛目(Mallophagida)及鈍角亞目(Amblycerina)和絲角亞目(Ischnocerina),例如牛羽蝨屬(Bovicola spp.)、牛仔食蟲虻屬(Damalina spp.)、貓羽蝨屬(Felicola spp.)、勒蝨屬(Lepikentron spp.)、禽羽蝨屬(Menopon spp.)、嚙毛蝨屬(Trichodectes spp.)、毛羽蝨屬(Trimenopon spp.)、巨毛蝨屬(Trinoton spp.)、畜蝨屬(Werneckiella spp.);來自雙翅目(Diptera)及長角亞目(Nematocerina)和短角亞目(Brachycerina),例如斑蚊屬(Aedes spp.)、瘧蚊屬(Anopheles spp.)、黃虻屬(Atylotus spp.)、蜂虱蠅屬(Braula spp.)、麗蠅屬(Calliphora spp.)、金蠅屬(Chrysomyia spp.)、斑虻屬(Chrysops spp.)、家蚊屬(Culex spp.)、庫蠓屬(Culicoides spp.)、真蚋屬(Eusimulium spp.)、廁蠅屬(Fannia spp.)、胃蠅屬(Gasterophilus spp.)、舌蠅屬(Glossina spp.)、血蠅屬(Haematobia spp.)、麻虻屬(Haematopota spp.)、蝨蠅屬(Hippobosca spp.)、瘤虻屬(Hybomitra spp.)、齒股蠅屬(Hydrotaea spp.)、皮蠅屬(Hypoderma spp.)、鹿蝨蠅屬(Lipoptena spp.)、綠蠅屬(Lucilia spp.)、羅蛉屬(Lutzomyia spp.)、蜱蠅屬(Melophagus spp.)、莫蠅屬(Morellia spp.)、家蠅屬(Musca spp.)、短蚋屬(Odagmia spp.)、狂蠅屬(Oestrus spp.)、菲蠓屬(Philipomyia spp.)、白蛉屬(Phlebotomus spp.)、鼻狂蠅屬(Rhinoestrus spp.)、肉蠅屬(Sarcophaga spp.)、蚋屬(Simulium spp.)、廄蠅屬(Stomoxys spp.)、虻屬(Tabanus spp.)、大蚊屬(Tipula spp.)、維蚋屬(Wilhelmia spp.)、汙蠅屬(Wohlfahrtia spp.);來自蚤目(Siphonapterida),例如角葉蚤屬(Ceratophyllus spp.)、櫛頭蚤屬 (Ctenocephalides spp.)、蚤屬(Pulex spp.)、潛蚤屬(Tunga spp.)、鼠蚤屬(Xenopsylla spp.);來自異翅目(Heteropterida),例如臭蟲屬(Cimex spp.)、錐蝽屬(Panstrongylus spp.)、紅獵蝽屬(Rhodnius spp.)、獵蝽屬(Triatoma spp.);以及來自蠊目(Blattarida)的滋擾和衛生性害蟲。
另外,在節肢動物的例子中,可以實例方式述及而非限制下列的蜱蟎亞綱:來自蜱蟎亞綱(Acari(Acarina))及後氣門亞目(Metastigmata),例如來自軟蜱科(argasidae)家族,諸如銳緣蜱屬(Argas spp.)、鈍緣蜱屬(Ornithodorus spp.)、耳蜱屬(Otobius spp.),來自硬蜱科(Ixodidae)家族,諸如花蜱屬(Amblyomma spp.)、革蜱屬(Dermacentor spp.)、血蜱屬(Haemophysalis spp.)、璃眼蜱屬(Hyalomma spp.)、硬蜱屬(Ixodes spp.)、扇頭蜱屬(Rhipicephalus(牛蜱屬(Boophilus))spp)、扇頭蜱屬(多宿主蜱的原始屬);來自中氣門蟎目(mesostigmata),諸如刺皮蟎屬(Dermanyssus spp.)、禽刺蟎屬(Ornithonyssus spp.)、肺刺蟎屬(Pneumonyssus spp.)、耳蟎屬(Raillietia spp.)、胸孔蟎屬(Sternostoma spp.)、熱厲蟎屬(Tropilaelaps spp.)、瓦蟎屬(Varroa spp.);來自輻蟎亞目(Actinedida)(前氣門亞目(Prostigmata)),例如蟎屬(Acarapis spp.)、姬螯蟎屬(Cheyletiella spp.)、毛囊蟎屬(Demodex spp.)、犛蟎屬(Listrophorus spp.)、肉蟎屬(Myobia spp.)、新恙蟎屬(Neotrombiculla spp.)、禽螯蟎屬(Ornithocheyletia spp.)、瘡蟎屬(Psorergates spp.)、恙蟎屬(Trombicula spp.);及來自粉蟎亞目(Acaridida)(無氣門亞目(Astigmata)),例如粉蟎屬(Acarus spp.)、嗜木蟎屬(Caloglyphus spp.)、足癢蟎屬(Chorioptes spp.)、胞蟎屬(Cytodites spp.)、頸下蟎屬(Hypodectes spp.)、腳蟎屬(Knemidocoptes spp.)、雞雛蟎屬(L胺基sioptes spp.)、痂蟎屬(Notoedres spp.)、耳癢蟎屬(Otodectes spp.)、癢蟎屬(Psoroptes spp.)、翅蟎屬(Pterolichus spp.)、疥蟎屬(Sarcoptes spp.)、疥癬恙蟲屬(Trixacarus spp.)、食酪蟎屬(Tyrophagus spp.)。
寄生性原生動物的實例包括但不限於:毛蟲綱(Mastigophora)(鞭毛蟲綱(Flagellata)),諸如:後滴門(Metamonada):來自雙滴蟲目(Diplomonadida),例如梨形鞭毛蟲屬(Giardia spp.)、旋核六鞭毛蟲屬(Spironucleus spp.);副基體綱(Parabasala):來自毛滴蟲目(Trichomonadida),例如組織鞭毛蟲(Histomonas spp.)、腸道鞭毛蟲屬(Pentatrichomonas spp.)、雞滴蟲屬(Tetratrichomonas spp.)、毛滴蟲屬(Trichomonas spp.)、滴蟲屬(Tritrichomonas spp.);眼蟲(Euglenozoa):來自錐體蟲目(Trypanosomatida):例如利什曼屬(Leishmania spp.)、錐蟲屬(Trypanosoma spp.);肉質鞭毛蟲門(Sarcomastigophora)(根足亞綱(Rhizopoda)),諸如內變形蟲科(Entamoebidae),例如阿米巴屬(Entamoeba spp.),中間阿米巴目(Centramoebidae),例如有棘變形蟲屬(Acanthamoeba spp.),真阿米巴屬(Euamoebidae),例如阿米巴變形蟲(Hartmanella spp.);囊泡蟲(Alveolata),諸如頂複門(Apicomplexa)(孢子蟲門(Sporozoa)):例如隱孢子蟲屬(Cryptosporidium spp.);來自艾美蟲目(Eimeriida),例如貝諾孢子蟲屬(Besnoitia spp.)、囊等胞球蟲屬(Cystoisospora spp.)、艾美球蟲屬(Eimeria spp.)、哈芒球蟲屬(Hammondia spp.)、等孢球蟲屬(Isospora spp.)、新包蟲屬(Neospora spp.)、肉孢子蟲屬(Sarcocystis spp.)、弓漿蟲屬(Toxoplasma spp.);來自阿德雷德目(Adeleida),例如肝簇蟲屬(Hepatozoon spp.)、真球蟲屬(Klossiella spp.);來自血孢子蟲目(Haemosporida),例如住血白冠原蟲屬(Leucocytozoon spp.)、瘧原蟲屬(Plasmodium spp.);來自梨形目(Piroplasmida\,例如巴倍蟲屬原蟲屬(Babesia spp.)、纖毛蟲屬(Ciliophora spp.)、Echinozoon spp.、泰勒蟲屬(Theileria spp.);來自Vesibuliferida,例如大腸纖毛蟲屬(Balantidium spp.)、布克斯頓纖毛蟲屬(Buxtonella spp.);微孢子蟲(Microspora),諸如隱胞子蟲屬(Encephalitozoon spp.)、腸胞微 孢子蟲屬(Enterocytozoon spp.)、球孢子蟲屬(Globidium spp.)、蜂微粒子蟲屬(Nosema spp.),以及例如黏體動物屬(Myxozoa spp.)。
使人類或動物致病的蠕蟲包括例如棘頭動物門(Acanthocephala)、線蟲動物門(Nematoden)、舌形動物門(Pentastoma)和扁形動物門(Platyhelminthes)(例如單殖吸蟲亞綱(Monogenea)、絛蟲(cestode)和吸蟲(trematode)).
例證的蠕蟲包括但不限於:單殖吸蟲亞綱(Monogenea):例如:指標蟲屬(Dactylogyrus spp.)、三代蟲屬(Gyrodactylus spp.)、同盤吸蟲屬(Microbothrium spp.)、多盤吸蟲屬(Polystoma spp.)、楚發蟲屬(Troglecephalus spp.);絛蟲:來自擬葉目(Pseudophyllidea),例如:吸葉絛蟲屬(Bothridium spp.)、廣節裂頭絛蟲屬(Diphyllobothrium spp.)、大複殖門絛蟲屬(Diphlogonoporus spp.)、艾呦蟲屬(Ichthyobothrium spp.)、舌狀絛蟲屬(Ligula spp.)、裂頭絛蟲(Schistocephalus spp.)、螺旋體蟲屬(Spirometra spp.);來自圓葉目(Cyclophyllida),例如:德里絛蟲屬(Andyra spp.)、裸頭絛蟲屬(Anoplocephala spp.)、無卵黃腺絛蟲屬(Avitellina spp.)、伯特絛蟲屬(Bertiella spp.)、彩帶絛蟲屬(Cittotaenia spp.)、戴維絛蟲屬(Davainea spp.)、雙睾絛蟲屬(Diorchis spp.)、倍殖孔絛蟲屬(Diplopylidium spp.)、複孔絛蟲屬(Dipylidium spp.)、棘球絛蟲屬(Echinococcus spp.)、棘殼絛蟲屬(Echinocotyle spp.)、棘鱗絛蟲屬(Echinolepis spp.)、泡尾絛蟲屬(Hydatigera spp.)、膜殼絛蟲屬(Hymenolepis spp.)、喬耶絛蟲屬(Joyeuxiella spp.)、中殖孔絛蟲屬(Mesocestoides spp.)、蒙尼絛蟲屬(Moniezia spp.)、副裸頭絛蟲屬(Paranoplocephala spp.)、瑞列絛蟲屬(Raillietina spp.)、斯泰絛蟲屬(Stilesia spp.)、帶狀絛蟲屬(Taenia spp.)、曲子宮絛蟲屬(Thysaniezia spp.)、繸體絛蟲屬(Thysanosoma spp.);吸蟲綱:來自復殖亞綱(Digenea),例如:澳血吸蟲屬(Austrobilharzia spp.)、短咽吸蟲屬(Brachylaima spp.)、杯殖吸蟲屬(Calicophoron spp.)、下殖吸蟲屬(Catatropis spp.)、支睪吸蟲屬(Clonorchis spp.)、表孔吸蟲屬(Collyriclum spp.)、殖盤吸蟲屬(Cotylophoron spp.)、環腸吸蟲屬(Cyclocoelum spp.)、雙腔吸蟲屬(Dicrocoelium spp.)、雙穴吸蟲屬(Diplostomum spp.)、棘隙吸蟲屬(Echinochasmus spp.)、棘緣吸蟲屬(Echinoparyphium spp.)、棘口吸蟲屬(Echinostoma spp.)、闊盤吸蟲屬(Eurytrema spp.)、肝吸蟲屬(Fasciola spp.)、擬片形吸蟲屬(Fasciolides spp.)、片形吸蟲屬(Fasciolopsis spp.)、菲策吸蟲屬(Fischoederius spp.)、腹袋吸蟲屬(Gastrothylacus spp.)、巨血吸蟲屬(Gigantobilharzia spp.)、巨盤吸蟲屬(Gigantocotyle spp.)、異型吸蟲屬(Heterophyes spp.)、低頸吸蟲屬(Hypoderaeum spp.)、彩蚴吸蟲屬(Leucochloridium spp.)、後殖吸蟲屬(Metagonimus spp.)、次睾吸蟲屬(Metorchis spp.)、侏形吸蟲屬(Nanophyetus spp.)、背孔吸蟲屬(Notocotylus spp.)、後睪吸蟲屬(Opisthorchis spp.)、鳥血吸蟲屬(Ornithobilharzia spp.)、肺吸蟲屬(Paragonimus spp.)、同盤吸蟲屬(Paramphistomum spp.)、斜睾吸蟲屬(Plagiorchis spp.)、莖雙穴吸蟲屬(Posthodiplostomum spp.)、前殖吸蟲屬(Prosthogonimus spp.)、血吸蟲屬(Schistosoma spp.)、毛血吸蟲屬(Trichobilharzia spp.)、隱孔吸蟲屬(Troglotrema spp.)、盲腔吸蟲屬(Typhlocoelum spp.);線蟲:來自毛形亞目(Trichinellida),例如:絲蟲屬(Capillaria spp.)、旋毛蟲屬(Trichinella spp.)、線蟲屬(Trichomosoides spp.)、毛首線蟲屬(Trichuris spp.);來自墊刃線蟲目(Tylenchida),例如:細絲鯰屬(Micronema spp.)、Parastrangyloides spp.、糞桿線蟲屬(Strongyloides spp.);來自短棒線蟲亞目(Rhabditida),例如:貓圓線蟲屬(Aelurostrongylus spp.)、裂口線蟲屬(Amidostomum spp.)、鉤蟲屬(Ancylostoma spp.)、血管圓線蟲屬(Angiostrongylus spp.)、氣管線蟲屬(Bronchonema spp.)、仰口線蟲屬 (Bunostomum spp.)、夏氏線蟲屬(Chabertia spp.)、古柏線蟲屬(Cooperia spp.)、類古柏線蟲屬(Cooperioides spp.)、環棘線蟲屬(Crenosoma spp.)、盅口線蟲屬(Cyathostomum spp.)、類圓線蟲屬(Cyclococercus spp.)、環齒口線蟲屬(Cyclodontostomum spp.)、杯環線蟲屬(Cylicocyclus spp.)、杯冠線蟲屬(Cylicostephanus spp.)、柱咽線蟲屬(Cylindropharynx spp.)、囊尾線蟲屬(Cystocaulus spp.)、網尾線蟲屬(Dictyocaulus spp.)、鹿圓線蟲屬(Elaphostrongylus spp.)、類絲蟲屬(Filaroides spp.)、球頭線蟲屬(Globocephalus spp.)、圖紋屬(Graphidium spp.)、輻首線蟲屬(Gyalocephalus spp.)、血矛線蟲屬(Haemonchus spp.)、螺旋線蟲屬(Heligmosomoides spp.)、豬圓線蟲屬(Hyostrongylus spp.)、馬什線蟲屬(Marshallagia spp.)、後圓線蟲屬(Metastrongylus spp.)、繆勒線蟲屬(Muellerius spp.)、鉤蟲屬(Necator spp.)、細頸線蟲(Nematodirus spp.)、新圓線蟲屬(Neostrongylus spp.)、日本圓線蟲屬(Nippostrongylus spp.)、尖柱線蟲屬(Obeliscoides spp.)、食管齒線蟲屬(Oesophagodontus spp.)、食道口線蟲屬(Oesophagostomum spp.)、盤尾絲蟲屬(Ollulanus spp.)、豬圓屬(Ornithostrongylus spp.)、奧斯勒屬(Oslerus spp.)、奧斯特線蟲屬(Ostertagia spp.)、副古柏線蟲屬(Paracooperia spp.)、副環棘線蟲屬(Paracrenosoma spp.)、副類絲蟲屬(Parafilaroides spp.)、副鹿圓線蟲屬(Parelaphostrongylus spp.)、肺尾線蟲屬(Pneumocaulus spp.)、肺圓蟲屬(Pneumostrongylus spp.)、盂口線蟲屬(Poteriostomum spp.)、原圓線蟲屬(Protostrongylus spp.)、尖尾線蟲亞屬(Spicocaulus spp.)、冠尾線蟲屬(Stephanurus spp.)、圓線蟲屬(Strongylus spp.)、比翼線蟲屬(Syngamus spp.)、背帶線蟲屬(Teladorsagia spp.)、盅口線蟲屬(Trichonema spp.)、毛圓線蟲屬(Trichostrongylus spp.)、三齒線蟲屬(Triodontophorus spp.)、短竇圓線蟲屬(Troglostrongylus spp.)、彎口線蟲屬(Uncinaria spp.);來自旋尾線蟲目(Spirurida),例如:棘唇屬(Acanthocheilonema spp.)、異尖線蟲屬(Anisakis spp.)、禽蛔蟲屬(Ascaridia spp.)、蛔蟲屬(Ascaris spp.)、 螺咽屬(Ascarops spp.)、無刺線蟲屬(Aspiculuris spp.)、貝利斯蛔蟲屬(Baylisascaris spp.)、布氏絲蟲屬(Brugia spp.)、Cercopithifilaria spp.、毛體線蟲屬(Crassicauda spp.)、雙瓣絲蟲屬(Dipetalonema spp.)、血直絲蟲屬(Dirofilaria spp.)、龍線蟲屬(Dracunculus spp.)、德斯線蟲屬(Draschia spp.)蟯蟲屬(Enterobius spp.)、絲狀蟲屬(Filaria spp.)、顎口線蟲屬(Gnathostoma spp.)、筒線蟲屬(Gongylonema spp.)、麗線蟲屬(Habronema spp.)、異刺線蟲屬(Heterakis spp.)、光絲蟲屬(Litomosoides spp.)、羅阿絲蟲屬(Loa spp.)、蟠尾絲蟲屬(Onchocerca spp.)、尖尾線蟲屬(Oxyuris spp.)、副柔線蟲屬(Parabronema spp.)、副絲蟲屬(Parafilaria spp.)、副蛔屬(Parascaris spp.)、栓尾線蟲屬(Passalurus spp.)、泡翼線蟲屬(Physaloptera spp.)、馬蟯蟲屬(Probstmayria spp.)、假絲蟲屬(Pseudofilaria spp.)、腹腔絲蟲屬(Setaria spp.)、Skjrabinema spp.、尾旋屬(Spirocerca spp.)、冠絲蟲屬(Stephanofilaria spp.)、圓線蟲屬(Strongyluris spp.)、管狀線蟲屬(Syphacia spp.)、吸吮線蟲屬(Thelazia spp.)、弓蛔屬(Toxascaris spp.)、弓首線蟲屬(Toxocaraspp.)、吳策絲蟲屬(Wuchereria spp.);棘頭動物門(Acanthocephala):來自少棘目(Oligacanthorhynchida),例如:巨吻棘頭蟲屬(Macracanthorhynchus spp.)、前睾棘頭蟲屬(Prosthenorchis spp.);來自念珠目(Moniliformida),例如:聯珠狀棘頭蟲屬(Moniliformis spp.);來自多形目(Polymorphida),例如:細頸棘頭蟲屬(Filicollis spp.);來自棘吻目(Echinorhynchida),例如棘頭蟲屬(Acanthocephalus spp.)、魚棘頭蟲屬(Echinorhynchus spp.)、似細吻棘頭蟲屬(Leptorhynchoides spp.);舌形動物門(Pentastoma):來自孔頭蟲目(Porocephalida),例如舌形蟲屬(Linguatula spp.)。
在獸醫領域及動物飼養中,式(I)化合物可藉由本技術中概括已知的方法以適合的製劑投予,諸如經腸、非經腸、經皮膚或經鼻途徑。投予可為 預防性、後預防性(metaphylactic)或治療性。
因此,本發明的一個實施態樣關於用作為藥劑之式(I)化合物。
另一態樣關於用作為抗體內寄生蟲劑之式(I)化合物。
本發明的另一態樣關於用作為驅蟲劑之式(I)化合物,尤其用作為殺線蟲劑、殺扇形動物劑(platyxelminthicide)、殺棘頭動物劑(acanthocephalicide)或殺舌形動物劑(pentastomicide)。
本發明的另一特定態樣關於用作為抗原蟲劑之式(I)化合物。
另一特定態樣關於抗體外寄生蟲劑之式(I)化合物,尤其為殺節肢動物劑,最特別為殺昆蟲劑或殺蟎劑。
本發明的其他態樣為獸醫用藥調配物,其包含有效量的至少一種式(I)化合物及至少一種下列者:醫藥上可接受之賦形劑(例如固態或液態稀釋劑)、醫藥上可接受之輔助劑(例如介面活性劑),尤其為習知用於獸醫用藥調配物中的醫藥上可接受之賦形劑及/或習知用於獸醫用藥調配物中的醫藥上可接受之輔助劑。
本發明相關的態樣為製造如本文所述之獸醫用藥調配物之方法,其包含將至少一種式(I)化合物與醫藥上可接受之賦形劑及/或輔助劑混合的步驟,尤其與習知用於獸醫用藥調配物中的醫藥上可接受之賦形劑及/或習知用於獸醫用藥調配物中的輔助劑混合。
本發明的另一特定的態樣為選自根據本發明所述及之態樣的殺體外寄生蟲及殺體內寄生蟲調配物之群組的獸醫用藥調配物及其製造方法,尤其選自驅蟲、抗原蟲及殺節肢動物調配物之群組,最特別地選自殺線蟲、殺扇形動物、殺棘頭動物、殺舌形動物、殺昆蟲及殺蟎調配物之群組。
另一態樣關於處理寄生蟲感染之方法,尤其為由選自本文所述及之體外寄生蟲及體內寄生蟲之群組的寄生蟲所引起的感染,該方法係藉由在對其有需要的動物中使用有效量的式(I)化合物,尤其在非人類動物中。
另一態樣關於處理寄生蟲感染之方法,尤其為由選自本文所述及之體 外寄生蟲及體內寄生蟲之群組的寄生蟲所引起的感染,該方法係藉由在對其有需要的動物中使用如本文所定義之獸醫用藥調配物,尤其在非人類動物中。
另一態樣關於式(I)化合物處理在動物(尤其為非人類動物)中的寄生蟲感染之用途,尤其為由選自本文所述及之體外寄生蟲及體內寄生蟲之群組的寄生蟲所引起的感染。
在動物健康或獸醫用藥的上下文中,術語「處理」包括為預防性、後預防性或治療性處理。
在特別的實施態樣中,以此方式提供用於獸醫用藥領域的至少一種式(I)化合物與其他活性化合物,尤其與殺體內及殺體外寄生蟲之混合物。
在動物健康領域中,「混合物」不僅意指兩種(或更多種)不同的活性化合物調配成共同的調配物且相應地一起使用,並亦關於包含分成各活性化合物的調配物之產品。因此,當欲使用兩種以上的活性化合物時,可將所有的活性化合物調配成共同的調配物或可將所有的活性化合物調配成單獨的調配物;同樣地可想像為混合形式,其中將一些活性化合物調配在一起及將一些活性化合物單獨調配。容許單獨的調配物單獨或連續施予討論中的活性化合物。
在此以彼等的「通用名稱」具體指定之活性化合物為已知且說明於例如The“Pesticide Manual”中(參見上文)或可於網路上搜尋(例如http://www.alanwood.net/pesticides)。
來自作為混合組份的殺體外寄生蟲劑之群組的例示性活性化合物(沒有任何應以其構成限制的意圖)包括在上文詳細列示之殺昆蟲劑及殺蟎劑。更多可用的活性化合物係依照目前的作用分類方案之IRAM模式列示於下:(1)乙醯膽鹼酯酶(AChE)抑制劑;(2)GABA-門控之氯化物通道阻斷劑;(3)鈉通道調節劑;(4)菸鹼能乙醯膽鹼受體(nAChR)競爭調節劑;(5)菸鹼能乙醯膽鹼受體(nAChR)異位作用調節劑;(6)麩胺酸門控之氯化物通道(GluCl) 異位作用調節劑;(7)幼保激素模擬物;(8)混雜的非特異性(多位置)抑制劑;(9)弦音器調節劑;(10)蟎生長抑制劑;(12)粒腺體ATP合成酶抑制劑,諸如ATP幹擾劑;(13)經由幹擾質子梯度之氧化性磷酸化去偶合劑;(14)菸鹼能乙醯膽鹼受體通道阻斷劑;(15)幾丁質生物合成抑制劑,第0型;(16)幾丁質生物合成抑制劑,第I型;(17)蛻皮幹擾劑(尤其在雙翅目之情況);(18)脫皮激素受體促效劑;(19)章魚胺能受體促效劑;(21)粒腺體複合物I電子傳輸;(25)粒腺體複合物II電子傳輸;(20)粒腺體複合物III電子傳輸;(22)電壓依賴性鈉通道阻斷劑;(23)乙醯基-Co-A羧酸酶抑制劑;(28)理安諾鹼受體調節劑;具有未知或非特異性作用機制之活性化合物,例如芬第芳尼(fentrifanil)、芬諾沙克(fenoxacrim)、氯戊二烯(cycloprene)、氯苯偶醯化物(clorobenzilate)、氯二美奉(chlordimeform)、弗苯西明(flubenzimin)、代塞拉尼(dicyclanil)、醯胺扶滅(amidoflumet)、喹甲二磺酸鹽(quinomethionat)、三苯噻蟎吩(triarathene)、氯噻唑苯(clothiazoben)、四殺(tetrasul)、油酸鉀、石油、美多沙代松(metoxadiazone)、棉普雷(gossyplur)、福特淨(flutenzine)、新殺蟎(溴propylate)、冰晶石(cryolite);來自其他類別的化合物,例如布塔克(butacarb)、代米提嵐(dimetilan)、除線威(cloethocarb)、磷克(phosphocarb)、亞特松-乙基(pirimiphos-ethyl)、巴拉松-乙基(parathion-ethyl)、甲克利弗(methacrifos)、o-水楊酸異丙酯、三氯松(trichlorfon)、硫普弗(sulprofos)、普巴磷(propaphos)、西布弗(sebufos)、吡達松(pyridathion)、普索(prothoate)、二氯芬松(dichlofenthion)、滅多松(demeton)-S-甲基碸、艾沙弗(isazofos)、氰芬磷(cyanofenphos)、代利弗(dialifos)、卡波苯硫(carbophenothion)、奧他硫松(autathiofos)、阿隆芬文松(aromfenvinfos)(-甲基)、吖磷(azinphos)(-ethyl)、氯吡弗(chlorpyrifos)(-ethyl)、弗美塞嵐(fosmethilan)、碘芬磷(iodofenphos)、二氧雜苯弗(dioxabenzofos)、弗目松(formothion)、芳諾弗(fonofos)、氟吡唑弗 (flupyrazofos)、芬硫松(fensulfothion)、伊曲弗(etrimfos);有機氯化合物,例如毒殺芬(camphechlor)、靈丹(lindane)、飛佈達(heptachlor);或苯基吡唑,例如亞多普(acetoprole)、比拉扶普((pyrafluprole)、比利普(pyriprole)、繁尼利普(vaniliprole)、維吉黴素(sisapronil);或異唑啉,例如賽蘭(sarolaner)、艾伏樂(afoxolaner)、樂地蘭(lotilaner)、氟樂(fluralaner);擬除蟲菊酯(pyrethroid),例如(順式-,反式-)甲氧苄氟菊酯(metofluthrin)、普福寧(profluthrin)、氟芬普(flufenprox)、福布賽寧特(flubrocythrinate)、福芬普(fubfenprox)、芬福寧(fenfluthrin)、普垂芬布(protrifenbut)、必滅寧(pyresmethrin)、RU15525、環戊烯丙菊酯(terallethrin)、順式-雷滅寧(cis-resmethrin)、氯氟醚菊酯(heptafluthrin)、百索美寧(bioethanomethrin)、百普美寧(biopermethrin)、芬比寧(fenpyrithrin)、順式-賽滅寧(cis-cypermethrin)、順式-環西寧(cis-permethrin)、可塞寧(clocythrin)、賽洛寧(cyhalothrin)(λ-)、氯波寧(chlovaporthrin)或鹵化烴化合物(HCH),新菸鹼類(neonicotinoid),例如尼塞(nithiazine)、二氯滅齊(dicloromezotiaz)、三氟普靈(triflumezopyrim),巨環內酯,例如奈馬克丁(nemadectin)、伊維菌素(ivermectin)、拉地克汀(latidectin)、莫西菌素(moxidectin)、沙拉菌素(selamectin)、依普菌素(eprinomectin)、得拉滅克汀(doramectin)、因滅汀(emamectin)苯甲酸鹽、倍脈心肟(milbemycin oxime)、三普林(triprene)、保幼醚(epofenonane)、迪芬諾嵐(diofenolan);生物劑、荷爾蒙或費洛蒙,例如天然產品,例如蘇力菌素(thuringiensin)、十二碳二烯醇(codlemone)或印度苦楝組份;二硝基苯酚,例如白粉克(dinocap)、大脫蟎(dinobuton)、百那培克(binapacryl);苯甲醯脲,例如福查隆(fluazuron)、氟幼脲(penfluron);脒衍生物,例如氯甲丁奉(chlormebuform)、賽咪唑(cymiazole)、狄米查 斯(demiditraz);殺蜂蟹蟎劑,例如有機酸,例如甲酸、草酸。
來自作為混合組份的殺體內寄生蟲劑之群組的例示性活性化合物包括但不限於活性驅蟲化合物及活性抗原蟲活性化合物。
驅蟲活性化合物包括但不限於下列的活性殺線蟲、殺白蟻及/或殺絛蟲活性成分:來自巨環內酯類別,例如:依普菌素(eprinomectin)、阿巴汀(abamectin)、奈馬克丁(nemadectin)、莫西菌素(moxidectin)、得拉滅克汀(doramectin)、沙拉菌素(selamectin)、勒匹汀(lepimectin)、拉地克汀(latidectin)、密貝汀(milbemectin)、伊維菌素(ivermectin)、因滅汀(emamectin)、倍脈心(milbemycin);來自苯並咪唑和前苯並咪唑類別,例如:奧苯達唑(oxibendazole)、甲苯咪唑(mebendazole)、三氯苯咪唑(triclabendazole)、多保淨(thiophanate)、帕苯達唑(parbendazole)、奧芬達唑(oxfendazole)、奈托比胺(netobimin)、芬苯嗒唑(fenbendazole)、非班太爾(febantel)、噻苯咪唑(thiabendazole)、環苯嗒唑(cyclobendazole)、卡班唑(cambendazole)、丙硫咪唑-亞碸(albendazole-sulphoxide)、丙硫咪唑(albendazole)、氟苯嗒唑(flubendazole);來自縮肽(depsipeptide)類別,較佳為環狀縮肽;尤其為24-員環狀縮肽,例如:艾默德斯(emodepside)、PF1022A;來自四氫嘧啶類別,例如:摩朗得(morantel)、抗蟲靈(pyrantel)、酚嘧啶(oxantel);來自咪唑並噻唑類別,例如:布他米唑(butamisole)、左旋咪唑(levamisole)、驅蟲凈(tetramisole);來自胺基苯脒類別,例如:阿米太爾(amidantel)、脫醯基阿米登太(deacylated amidantel)(dAMD)、三苯雙脒(tribendimidine);來自胺基乙腈類別,例如:莫涅潘托(monepantel); 來自巴拉赫克醯胺(paraherquamide)類別,例如:巴拉赫克醯胺(paraherquamide)、得曲恩特(derquantel);來自水楊醯基苯胺別,例如:三溴沙侖(tribromsalan)、溴沙尼特(溴xanide)、溴替尼特(brotianide)、氯碘沙尼(clioxanide)、綠氰碘柳胺(closantel)、耐克螺(niclosamide)、氯羥柳胺(oxyclozanide)、碘醚柳胺(rafoxanide);來自經取代的苯酚類別,例如:硝碘酚腈(nitroxynil)、硫氯酚(bithionol)、二碘硝酚(disophenol)、六氯酚(hexachlorophene)、聯硝氯酚(niclofolan)、曼尼克洛芙蘭(meniclopholan);來自有機磷酸鹽類別,例如:三氯松(trichlorfon)、萘羅氟(naphthalofos)、二氯松(dichlorvos)/DDVP、育畜磷(crufomate)、蠅毒磷(coumaphos)、鹵氧酮(haloxone);來自呱酮/喹啉類別,例如:吡喹酮(praziquantel)、依西太爾(epsiprantel);來自呱類別,例如:呱、安泰樂(hydroxyzine);來自四環素類別,例如四環素、氯四環素、強力黴素(doxycycline)、羥四環素、羅利環素(rolitetracycline);來自各種其他類別,例如:丁萘脒(bunamidine)、尼立達唑(niridazole)、雷瑣太爾(resorantel)、歐姆泛洛丁(omphalotin)、奧替普拉(oltipraz)、硝硫氰酯(nitroscanate)、硝碘酚腈(nitroxynil)、奧沙尼喹(oxamniquin)、米拉散(mirasan)、米拉西(miracil)、硫蒽酮(lucanthon)、海恩酮(hycanthon)、海托啉(hetolin)、衣米丁(emetin)、枸據酸乙胺(diethylcarbamazine)、二氯芬(dichlorophen)、地芬泥素(diamfenetid)、克癲平錠(clonazepam)、苄芬寧(bephenium)、硝硫氰胺(amoscanate)、氯舒隆(clorsulon)。
抗原蟲活性化合物包括但不限於下列的活性化合物:來自三類別,例如:地克朱利(diclazuril)、波那朱利(ponazuril)、勒崔朱利(letrazuril)、托曲朱利(toltrazuril); 來自聚醚離子載體類別,例如:莫能黴素(monensin)、鹽黴素(salinomycin)、馬杜黴素(maduramicin)、甲基鹽黴素(narasin);來自巨環內酯類別,例如:米貝黴素類(milbemycin)、紅黴素(erythromycin);來自喹諾酮類別,例如:恩諾沙星(enrofloxacin)、潑度沙星(pradofloxacin);來自奎寧類別,例如:氯奎寧(chloroquine);來自嘧啶類別,例如:乙胺嘧啶(pyrimethamine);來自磺醯胺類別,例如:磺胺喹啉(sulfaquinoxaline)、甲氧苄啶(trimethoprim)、磺胺氯吡(sulfaclozin);來自硫胺類別,例如:氨丙啉(amprolium);來自林可醯胺(lincosamide)類別,例如:克林黴素(clindamycin);來自碳醯苯胺類別,例如:雙咪苯脲(imidocarb);來自硝基呋喃類別,例如:硝呋替莫(nifurtimox);來自喹唑啉酮生物鹼類別,例如:常山酮(halofuginone);來自各種其他類別,例如:奧沙尼喹(Oxamniquin)、巴龍黴素(Paromomycin);來自疫苗或微生物抗原類別,例如:羅氏犬巴貝斯原蟲(Babesia canis rossi)、柔嫩艾美球蟲(Eimeria tenella)、早熟艾美球蟲(Eimeria praecox)、毒害艾美球蟲(Eimeria necatrix)、和緩艾美球蟲(Eimeria mitis)、巨型艾美球蟲(Eimeria maxima)、布氏艾美球蟲(Eimeria brunetti)、堆型艾美球蟲(Eimeria acervulina)、澳氏犬巴貝斯原蟲(Babesia canis vogeli)、幼小利什曼原蟲(Leishmania infantum)、犬巴貝斯原蟲(Babesia canis canis)、牛肺蟲(Dictyocaulus viviparus)。
所有述及之混合物組份亦可視情況可以適合的鹼或酸形成鹽類,假設彼等係基於彼等的官能基而能夠因此達成。
式(I)化合物亦可用於病媒控制。在本發明的上下文中,病媒為節肢動物,尤其為昆蟲或蜘蛛綱,能夠從儲體(植物、動物、人類等等)傳播病原體(例如病毒、蠕蟲、單細胞有機體和細菌)至宿主。病原體可以機械性傳播(例如藉由非叮咬性蒼蠅造成的沙眼)至宿主或藉由注射傳播(例如由蚊子傳播瘧疾寄生蟲)至宿主。
病媒及由彼等傳播之疾病或病原體的實例為:
- 瘧蚊:瘧疾、絲蟲病;- 家蚊:日本腦炎、絲蟲病、其他的病毒疾病、其他的蠕蟲傳播;- 埃及斑蚊:黃熱病、登革熱、更多的病毒疾病、絲蟲病、;- 蚋科:蠕蟲傳播,尤其為蟠尾絲蟲(Onchocerca volvulus);- 蛾蚋科:利什曼病(leishmaniasis)傳播2)蝨子:皮膚感染、流行性斑疹傷寒(epidemic typhus);3)跳蚤:瘟疫、地方性斑疹傷寒、絛蟲;4)蒼蠅:昏睡症(錐蟲病);霍亂或其他的細菌疾病;5)蟎:疥蟲病(acariosis)、流行性斑疹傷寒、立克次痘疹(rickettsialpox)、兔熱病、聖路易腦炎(Saint Louis encephalitis)、壁蝨傳播的腦炎(TBE)、克裡米亞-剛果出血熱(rimean-Congo haemorrhagic fever)、疏螺旋體病(borreliosis);6)壁蝨:疏螺旋體病(諸如中非洲回歸熱螺旋體(Borrelia duttoni))、壁蝨傳播的腦炎、Q熱病(蒲納氏科克斯氏菌(Coxiella burnetii))、焦蟲病(犬焦蟲(Babesia canis canis))、艾利希氏體症(ehrlichiosis)。
在本發明的上下文中,病媒的實例為昆蟲,例如蚜蟲、蒼蠅、葉蟬或牧草蟲,其能夠傳播植物病毒至植物。其他能夠傳播植物病毒的病媒為蜘蛛蟎、蝨子、甲蟲和線蟲。
在本發明的上下文中,病媒的更多實例為可傳播病原體至動物及/或人類的昆蟲和蜘蛛綱,諸如蚊子,尤其為埃及斑蚊屬,瘧蚊(Anopheles),例如岡比亞瘧蚊(A.gambiae)、阿拉伯按蚊(A.arabiensis)、非涅斯特按蚊(A.funestus)、大劣按蚊(A.dirus)(瘧疾)和家蚊(Culex),蛾蚋科,諸如白蛉屬(Phlebotomus)、羅蛉屬(Lutzomyia),蝨子、跳蚤、蒼蠅、蟎和壁蝨。
若式(I)化合物具有抗性破壞,則病媒控制亦為可行的。
式(I)化合物適合於預防疾病及/或由病媒傳播的病原體。因此,本發明的另一態樣為式(I)化合物用於病媒控制之用途,例如用於農業、園藝、花園和休閒設施中,且亦用於保護原料和儲存產品中。
式(I)化合物適合於保護工業原料對抗昆蟲的感染或破壞,例如來自鞘翅目(Coleoptera)、膜翅目(Hymenoptera)、等翅目(Isoptera)、鱗翅類(Lepidoptera)、嚙蟲目(Psocoptera)和衣魚(Zygentoma)之昆蟲。
應瞭解本發明上下文中的工業原料意指非動物性原料,諸如較佳為塑膠、黏著劑、膠水、紙張和紙板、皮革、木材、加工木製品和塗料組成物。使用本發明保護木材特別佳。
在另外的實施態樣中,式(I)化合物係與至少一種其他的殺昆蟲劑及/或至少一種殺真菌劑一起使用。
在另外的實施態樣中,式(I)化合物係呈即用型殺蟲劑形式,亦即該等可不進一步修飾而施予討論中的原料。更多有用的殺昆蟲劑或殺真菌劑尤其包括那些上文所述及者。
亦驚訝地發現式(I)化合物可用於保護與鹽水或半鹹水接觸之物品免於汙塞,特別為船體、隔板、編網、建築物、繫船設備和傳訊系統。同樣有可使用單獨或與其他活性化合物組合的式(I)化合物作為抗汙塞組成物。
式(I)化合物適合於控制衛生防區的動物害蟲。本發明可特別用於居家防區、衛生防區及保護庫存產品,特別用於控制在封閉空間中出現的昆蟲、蜘蛛、壁蝨和蟎,例如在公寓、廠房、辦公室、車廂、動物繁殖場所中。用於控制動物害蟲的式(I)化合物係單獨或與其他活性化合物及/或輔助劑組合使用。該等較佳地用於居家殺昆蟲劑產品中。式(I)化合物有效對抗敏感性及抗性物種,且對抗所有的發展階段。
該等害蟲包括例如來自蜘蛛綱、來自蠍目、蜘蛛目和盲珠目,來自唇足綱和倍足綱,來自昆蟲綱蜚蠊目,來自鞘翅目、革翅目、雙翅目、異翅亞目(Heteroptera)、膜翅目、等翅目、鱗翅目、毛蝨目、嚙蟲目、跳躍亞目或直翅目、隱翅目(Siphonaptera)和衣魚目,及來自軟甲亞綱(Malacostraca)等足目之害蟲。
進行施用係以在例如氣霧劑、無壓力噴灑產品(例如泵壓及霧化噴灑器)、自動成霧系統、成霧器、發泡物、凝膠、具有由纖維素或塑膠所製成之蒸發片的蒸發器產品、液體蒸發器、凝膠和薄膜式蒸發器、推進劑驅動式蒸發器、無能源或被動式蒸發系統、防蟲紙、防蟲袋和防蟲膠中,用作為粒狀或細粉,用於擴散式誘餌或誘餌台中來達成。
在室溫,將2-[6-(乙基氫硫基)噻吩并[3,2-b]呋喃-5-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(405mg,1.05mmol)溶於23ml DCM中,添加甲酸(243mg,5.28mmol)及過氧化氫溶液(aq.35%強度;719mg,7.39mmol),並將混合物攪拌12h,緩慢添加40%強亞硫酸氫鈉溶液至反應溶液中,並將混合物攪拌1h。移除有機相,以飽和碳酸氫鈉溶液洗滌,在硫酸鈉上乾燥並在旋轉蒸發器上除去溶劑。殘餘物以環己烷/乙酸乙酯梯度作為移動相,以管柱層析在矽凝膠上純化。
MH+:416;1H-NMR(400MHz,d-DMSO)δ ppm=9.27(s,1H),8.29(s,1H),8.23(d,1H),7.25(d,1H),3.92(s,3H),3.53-3.47(q,2H),1.19-1.16(t,3H).
將6-(乙基氫硫基)噻吩并[3,2-b]呋喃-5-羧酸(770mg,2.69mmol)溶於4ml二氯甲烷及0.02ml DMF,並冷卻至0℃。逐滴添加草醯氯(321mg, 26.9mmol),然後將混合物於室溫攪拌1h。在旋轉蒸發器上除去所有揮發性成分。將粗產物溶於10ml 1,4-二烷,並緩慢逐滴添加至N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(516mg,2.69mmol)之10ml二烷溶液。將反應溶液於90℃加熱12h。冷卻至室溫後,將矽凝膠添加至溶液,並在旋轉蒸發器上除去溶劑。以環己烷/乙酸乙酯梯度作為移動相,將殘餘物以管柱層析在矽凝膠上純化。
MH+:384;1H-NMR(400MHz,d-DMSO)δ ppm:9.21(s,1H),8.25(s,1H),7.18(d,1H),4.01(s,3H),3.14-3.08(q,2H),1.17-1.13(t,3H).
在氬氣壓下,2,2,6,6-四甲基哌啶(1.84g,13mmol)溶於50ml乾THF,並冷卻至-25℃。緩慢逐滴添加正丁基鋰(2.5M於己烷中,13mmol)並將混合物攪拌30min,將溶於5ml THF之噻吩并[3,2-b]呋喃-5-羧酸(1.00g,5.94mmol;可商業上獲得)逐滴添加至反應溶液,於-25℃攪拌30min之後,逐滴添加二硫化二乙基(1.82g,14.8mmol)並將混合物再攪拌30min。緩慢溫熱混合物至室溫,然後在旋轉蒸發器上濃縮。殘渣於環己烷吸收,並以過濾分離所產生之沉澱。有機相以1N氫氯酸溶液洗滌,在硫酸鈉上乾燥並清除溶劑。粗產物不須進一步純化使用於後續反應。
MH+:229;1H-NMR(400MHz,d-DMSO)δ ppm:8.12-8.09(m,1H),7.07(m,1H),3.33(m,2H),1.29(t,3H).
於室溫,將2-[3-(乙基氫硫基)-5-(三氟甲基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(55mg,0.09mmol)溶於3ml DCM。添加甲酸(22mg,0.48mmol)及過氧化氫溶液(aq.35% strength;65mg,0.67mmol),並將混合物攪拌12h。添加緩慢40%強度之亞硫酸氫鈉溶液至反應溶液,並將混合物攪拌1h。移除有機相,以飽和碳酸氫鈉溶液洗滌,在硫酸鈉上乾燥並在旋轉蒸發器上除去溶劑。以環己烷/乙酸乙酯梯度作為移動相,將殘餘物以管柱層析在矽凝膠上純化。
MH+:501;1H-NMR(400MHz,d-DMSO)δ ppm:9.32(s,1H),8.37(m,1H),8.34(m,1H),3.95(s,3H),3.62-3.57(q,2H),1.20-1.16(t,3H).
將3-(乙基氫硫基)-5-(三氟甲基)噻吩并[3,2-b]噻吩-2-羧酸(768mg,2.45mmol)溶於4ml二氯甲烷及0.09ml DMF,並冷卻至0℃。逐滴添加草 醯氯(3120mg,24.5mmol),然後將混合物於室溫攪拌1h。在旋轉蒸發器上除去所有揮發性成分,將粗產物溶於5ml 1,4-二烷並緩慢逐滴添加至含N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(417mg,2.45mmol)之17ml二烷溶液。於90℃加熱反應溶液12h。冷卻至室溫後,在旋轉蒸發器上除去溶劑。殘餘物吸收於乙酸乙酯並以水洗滌二次。有機相在硫酸鈉上乾燥並濃縮。以水/乙腈梯度作為移動相,將殘餘物以製備型HPLC之管柱層析純化。
MH+:468;1H-NMR(400MHz,d-DMSO)δ ppm:9.27(s,1H),8.35(m,1H),8.31(m,1H),4.01(s,3H),2.93-2.88(q,2H),1.06-1.03(t,3H).
在氬氣壓下,將2,2,6,6-四甲基哌啶(1.127g,8.0mmol)溶於95ml乾THF並冷卻至-25℃。緩慢逐滴添加正丁基鋰(2.5M於己烷中,8.0mmol),並將混合物攪拌30min。將溶於5ml THF之5-(三氟甲基)噻吩并[3,2-b]噻吩-2-羧酸(0.915g,3.62mmol)逐滴添加反應溶液。於-25℃攪拌30分鐘後,逐滴添加二硫化二乙基(1.109g,9.1mmol),並將混合物再攪拌30min。將該混合物緩慢溫熱至室溫,然後在旋轉蒸發器上濃縮。殘餘物吸收於環己烷並過濾分離所所產生的沉澱物。有機相以1N氫氯酸溶液清洗二次,在硫酸鈉上乾燥並清除溶劑,粗產物不須進一步純化使用於後續反應。
將5-(三氟甲基)噻吩并[3,2-b]噻吩-2-羧基甲酯(1.0g,3.75mmol)溶於10ml THF,添加溶於2ml水之LiOH(179mg,7.51mmol)。反應溶液於室溫攪拌12h,添加1N氫氯酸溶液並於在旋轉蒸發器上移除有機溶劑。在水相中,形成沉澱,並以過濾分離並風乾。
M(neg):251;1H-NMR(400MHz,d-DMSO)δ ppm:13.62(b-s,1H),8.23(s,1H),8.21(s,1H).
將3-溴-5-(三氟甲基)噻吩-2-甲醛(3.37g,13.0mmol)及碳酸鉀(2.76g,20.0mmol)一開始充填至50ml DMF並加熱至60℃。將巰基乙酸乙酯(1.4ml,13.0mmol)及催化量之18-冠-6醚逐滴添加至此混合物。將反應混合物攪拌12h,然後倒入500ml水中。混合物以乙酸乙酯萃取三次,合併之有機萃取物以飽和氯化鈉溶液洗滌二次及以水洗滌一次,在硫酸鎂上乾燥並濃縮。以環己烷/乙酸乙酯梯度作為移動相,殘餘物以管柱層析在矽凝膠上純化。
MH+:266;1H-NMR(400MHz,CDCl3)δ ppm:8.00(s,1H),7.65(s,1H),3.90(s,3H).
在氬氣下,將N,N-二異丙基胺(6.00ml,42.3mmol)溶於24ml乾THF,於-78℃逐滴添加正丁基鋰並將混合物攪拌45min。然後逐滴添加溶於24ml THF之4-溴-2-(三氟甲基)噻吩(7.50g,32.5mmol),並將混合物攪拌1h。添加含DMF(3.20ml,41.5mmol)之30ml THF,並將反應混合物攪拌1h,並在此期間緩慢溫熱至室溫。添加水並將混合物以乙酸乙酯萃取三次。合併之有機萃取物在硫酸鈉上乾燥並濃縮,以環己烷/乙酸乙酯梯度作為移動相,將殘餘物以管柱層析在矽凝膠上純化。
在室溫,將2-[3-(乙基氫硫基)-5-(三氟甲基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(175mg,0.41mmol)溶於12ml DCM,添加甲酸(94mg,2.05mmol)及過氧化氫溶液(aq.35%強度;279mg,2.87mmol)並將混合物攪拌12h。緩慢添加40%強度之亞硫酸氫鈉溶液至反應溶液中,並將該混合物攪拌1h。移除有機相,以飽和碳酸氫鈉溶液洗滌,在硫酸鈉上乾燥並在旋轉蒸發器上除去溶劑。以環己烷/乙酸乙酯 梯度作為移動相,將殘餘物以管柱層析在矽凝膠上純化。
MH+:416;1H-NMR(400MHz,d-DMSO)δ ppm:9.24(s,1H),8.26(s,1H),3.86(s,3H),3.35-3.30(m,4H),3.06-2.95(m,4H),1.15-1.11(t,3H).
將3-(乙基氫硫基)-5,6-二氫-4H-環戊[b]噻吩-2-羧酸(465mg,1.56mmol)溶於4ml二氯甲烷及0.02ml DMF中。冷卻至0℃,逐滴添加草醯氯(1992mg,15.6mmol),然後將混合物於室溫攪拌1h,在旋轉蒸發器上除去所有揮發性成分。粗產物溶於10ml 1,4-二烷,並緩慢逐滴添加至含N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(300mg,1.56mmol)之10ml二烷溶液。將反應溶液於90℃加熱12h。冷卻至室溫後,在旋轉蒸發器上除去溶劑。殘餘物吸收於乙酸乙酯,並以水洗滌二次。有機相在硫酸鈉上乾燥並濃縮。使用水/乙腈梯度作為移動相,將殘餘物以製備型HPLC管柱層析純化。
MH+:384;1H-NMR(400MHz,CDCl3)δ ppm:9.18(s,1H),8.22(s,1H),3.94(s,3H),3.32(m,2H),3.02-2.99(m,2H),2.83-2.80(m,2H),2.77-2.71(m,2H),1.05-1.01(t,3H).
在氬氣壓下,將2,2,6,6-四甲基哌啶(1.847g,13.0mmol)溶於20ml乾THF,並冷卻至-25℃。緩慢逐滴添加正丁基鋰(2.5M於己烷中,13.0mmol)並將混合物攪拌30min。逐滴添加溶於5ml THF之5,6-二氫-4H-環戊[b]噻吩-2-羧酸(1.00g,5.94mmol)至反應溶液。於-25℃攪拌30min之後,逐滴添加二硫化二乙基(1.816g,14.8mmol),並將混合物再攪拌30min。將混合物緩慢溫熱至室溫,然後在旋轉蒸發器上濃縮,殘餘物吸收於環己烷並過濾分離所所產生的沉澱物。有機相以1N氫氯酸溶液清洗二次,在硫酸鈉上乾燥並清除溶劑,粗產物不須進一步純化使用於後續反應。
MH+:229;1H-NMR(400MHz,CDCl3)δ ppm:3.06-3.01(q,2H),2.90-2.68(m,6H),1.17-1.14(t,3H).
於室溫,將2-[6-溴-3-(乙基氫硫基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(435mg,0.81mmol)溶於23ml DCM,添加甲酸(188mg,4.09mmol)及過氧化氫溶液(aq.35%強度;556mg,5.72 mmol),並將混合物攪拌12h,添加緩慢40%強度之亞硫酸氫鈉溶液至反應溶液,並將混合物攪拌1h。移除有機相,以飽和碳酸氫鈉溶液洗滌,在硫酸鈉上乾燥並在旋轉蒸發器上除去溶劑,以環己烷/乙酸乙酯梯度作為移動相,將殘餘物以管柱層析在矽凝膠上純化。
MH+:511;1H-NMR(400MHz,CDCl3)δ ppm:9.29(s,1H),8.32(s,1H),7.91(s,1H),3.93(s,3H),3.58-3.51(q,2H),1.19-1.14(t,3H).
將2-[3-(乙基氫硫基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(1.18g,2.95mmol)溶於35ml四氫呋喃,排除光線,添加N-溴琥珀醯亞胺(788.6mg,4.43mmol),並將混合物攪拌12h。反應混合物以乙酸乙酯稀釋,並以1N硫代硫酸鈉洗滌,移除有機相,在硫酸鈉上乾燥並在旋轉蒸發器上除去溶劑,粗產物以管柱層析(SiO2,環己烷、乙酸乙酯)純化。
MH+:480;1H-NMR(400MHz,CDCl3)δ ppm:9.25(s,1H),8.28(s,1H),7.87(s,1H),4.00(s,3H),2.91-2.85(q,2H),1.06-1.02(t,3H).
將2-(3-碘噻吩并[3,2-b]噻吩-2-基)-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(1.80g,3.86mmol)、乙硫醇(480.8mg,7.73mmol)、三(二亞苄基丙酮)二鈀(0)(177mg,0.19mmol)、4,5-雙二苯基膦-9,9-二甲基氧雜蒽(Xantphos)(223.9mg,0.38mmol)及二異丙基乙胺(0.85mg,6.57mmol)溶於乾二烷,並在在氬氣壓下,於80℃加熱3h。冷卻至室溫後,將矽凝膠添加至反應混合物,並在旋轉蒸發器上除去溶劑,粗產物經管柱層析(SiO2,環己烷/乙酸乙酯)於矽凝膠上純化。
MH+:400;1H-NMR(400MHz,CDCl3)δ ppm:9.24(s,1H),8.28(s,1H),7.96-7.795(d,1H),7.65-7.64(d,1H),4.00(s,3H),2.95-2.89(q,2H),1.07-1.04(t,3H).
在氬氣壓下,將噻吩并[3,2-b]噻吩-2-羧酸甲酯(5.00g,25.2mmol)溶於20ml乾四氫呋喃,將溶液冷卻至-60℃,並緩慢逐滴添加氯化四甲基哌啶鎂氯化鋰複合物(6.11g,25.2mmol,溶於1M之甲苯/四氫呋喃)。於-60℃攪拌1h後,逐滴添加碘(6.40g,25.2mmol,溶於10ml四氫呋喃)。將混合物緩慢溫熱至室溫,並添加200ml飽和氯化銨溶液,分離有機相,在旋轉蒸發器上除去溶劑,並將粗產物3-碘噻吩并[3,2-b]噻吩-2-羧酸甲酯直接 使用於後續反應。
將3-碘噻吩并[3,2-b]噻吩-2-羧酸甲酯(8.1g,25mmol)溶於100ml THF,並添加含氫氧化鋰(2.99g,125mmol)之20ml水。反應混合物於室溫激烈攪拌12h。將混合物以1N氫氯酸中和,並添加水。形成沉澱物(3-碘噻吩并[3,2-b]噻吩-2-羧酸),過濾分離。
將3-碘噻吩并[3,2-b]噻吩-2-羧酸(3.24g,10.4mmol)溶於4ml二氯甲烷,於0℃,添加0.02ml二甲基甲醯胺及草醯氯(13mg,104mmol)。反應混合物於室溫攪拌1h,然後於回流加熱1h,在旋轉蒸發器上除去所有揮發性成分,且醯氯維持溶於10ml 1,4-二烷。
緩慢逐滴添加溶於10ml二烷之N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(2.00g,10.4mmol),且為醯氯。反應混合物加熱至90℃ 12h。冷卻後,形成結晶,過濾分離。將母液濃縮並將殘餘物以管柱層析純化(SiO2,環己烷/乙酸乙酯)。
MH+:465;1H-NMR(400MHz,CDCl3)δ ppm:9.27(s,1H),8.31(s,1H),7.99-7.98(d,1H),7.81-7.80(d,1H),4.01(s,3H).
將2-[6-溴-3-(乙基磺醯基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(50mg,0.09mmol)、氰化鋅(11.5mg,0.09mmol)、三(二亞苄基丙酮)二鈀(0)(1.8mg,0.002mmol)及1,1'-雙(二苯基膦)二茂鐵x DCM("dppf x DCM",1.6mg,0.02mmol)溶於2ml DMF並於微波爐中於180℃加熱15min。反應混合物以MTBE稀釋,並以飽和碳酸氫鈉溶液洗滌二次。有機相在硫酸鈉上乾燥並在旋轉蒸發器上除去溶劑,殘餘物以管柱層析(SiO2,環己烷/乙酸乙酯)純化。
MH+:457;1H-NMR(400MHz,CDCl3)δ ppm:9.32(s,1H),8.54(s,1H),8.35(s,1H),3.95(s,3H),3.62-3.57(q,2H),1.19-1.15(t,3H).
將2-[6-溴-3-(乙基磺醯基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(50mg,0.09mmol)、乙醯胺(58mg,0.98mmol)、三(二亞苄基丙酮)二鈀(0)(9mg,0.01mmol)、碳酸銫(48mg,0.15mmol)、三氯甲烷(12mg,0.1mmol)及Xantphos(6mg,0.01mmol)溶於5ml 二烷,並於100℃加熱4h。冷卻至室溫後,反應溶液直接以製備型HPLC純化。
MH+:489;1H-NMR(400MHz,CDCl3)δ ppm:11.72(s,1H),9.27(s,1H),8.29(s,1H),7.19(s,1H),3.92(s,3H),3.54-3.48(q,2H),2.16(s,3H),1.24-1.14(t,3H).
在氬氣壓下,將2-[6-溴-3-(乙基磺醯基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(100mg,0.196mmol)、1-甲基-4-(4,4,5,5-四甲基-1,3,2-二硼烷-2-基)-1H-吡唑(45mg,0.216mmol)、四(三苯基膦)鈀(o)(11mg,0.01mmol)及碳酸鈉(83mg,0.78mmol)溶於3ml二烷,並於100℃加熱12h。
MH+:512;1H-NMR(400MHz,CDCl3)δ ppm:9.29(s,1H),8.31(s,1H),8.27(s,1H),7.90(s,1H),7.73(s,1H),5.76(s,1H),3.95(s,3H),3.90(s,3H),3.58-3.53(q,2H),1.20-1.17(t,3H).
在25ml高壓釜,將2-[6-溴-3-(乙基磺醯基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(200mg,0.39mmol)溶於5ml甲醇,並添加乙酸鈉(60mg,0.733mmol)及二氯[1,1-雙(二苯基膦)二茂鐵]鈀(II)丙酮加合物("J&M Pd-107",60mg,0.076mmol)。該設備用氬氣沖洗,3次。然後於5巴壓力之一氧化碳中,將混合物於40℃攪拌18h。在過濾移除所有固體後,將有機相濃縮並將粗產物6-(乙基磺醯基)-5-[3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶-2-基]噻吩并[3,2-b]噻吩-3-羧酸甲酯以製備型HPLC純化。
將6-(乙基磺醯基)-5-[3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶-2-基]噻吩并[3,2-b]噻吩-3-羧酸甲酯(29mg,0.06mmol)溶於1ml甲醇及1ml四氫呋喃,並添加銨(152mg,2.96mmol,33%,水溶液),混合物於室溫攪拌12h。添加矽凝膠後,去除所有揮發性成分,且粗產物藉由管柱層析於矽膠上純化。
MH+:475;1H-NMR(400MHz,CDCl3)δ ppm:9.30(s,1H),8.36(b-s,1H),8.33(s,1H),8.24(s,1H),7.76(b-s,1H),3.94(s,3H),3.57-3.51(q,2H),1.18-1.15(t,3H).
將2-[6-溴-3-(乙基氫硫基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(150mg,0.31mmol)、苯基硼酸(152mg,1.25mmol)、乙酸鈀(7mg,0.031mmol)、S-Phos(26mg,0.06mmol)及磷酸鉀(333mg,1.568mmol)溶於6ml甲苯及3mlTHF。混合物於回流加熱7h,冷卻至室溫後,添加矽凝膠並在旋轉蒸發器上除去所有揮發性成分,於矽凝膠上之殘餘物,2-[3-(乙基氫硫基)-6-苯基噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶以管柱層析純化。
於室溫,將2-[3-(乙基氫硫基)-6-苯基噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(77mg,0.15mmol)溶於23ml DCM。添加甲酸(37mg,0.8mmol)及過氧化氫溶液(aq.35%強度;110mg,1.13mmol),並將混合物攪拌12h,添加緩慢40%強度之亞硫酸氫鈉溶液至反應溶液,並將混合物攪拌1h,移除有機相,以飽和碳酸氫鈉溶液洗滌,在硫酸鈉上乾燥並在旋轉蒸發器上除去溶劑。以環己烷/乙酸乙酯梯度作為移動相,殘餘物以管柱層析在矽凝膠上純化。
MH+:508;1H-NMR(400MHz,CDCl3)δ ppm:9.30(s,1H),8.33(s,1H),8.11(s,1H),7.81-7.79(m,2H),7.54-7.50(m,2H),7.46-7.43(m,1H),3.96(s,3H),3.60-3.53(q,2H),1.22-1.18(t,3H).
在氬氣壓下,將2-[6-溴-3-(乙基磺醯基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(50ml,0.1mmol)、N-甲基脲(9mg,0.118mmol)、碳酸銫(48mg,0.15mmol)、4,5-雙(二苯基膦)-9,9-二甲基二苯并哌喃(6mg,0.01mmol)及三(二亞苄基丙酮)二鈀(0)溶於5ml乾脫氣二烷並於80℃加熱4h。.冷卻至室溫後,將混合物以製備型HPLC純化。
MH+:504;;1H-NMR(400MHz,CDCl3)δ ppm:9.25(s,1H),8.28(s,1H),6.96(s,1H),3.92(s,3H),3.53-3.47(q,2H),2.71-2.67(m,3H),1.18-1.14(t,3H).
在壓力容器中,將2-[6-溴-3-(乙基磺醯基)噻吩并[3,2-b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(100mg,0.19mmol)、4-氯-1H-吡唑(22mg,0.216mmol)、碘化亞銅(I)(4mg,0.02mmol)、反-N,N'-二甲基環己 烷-1,2-二胺(6mg,0.04mmol)、碘化鉀(10mg,0.06mmol)及碳酸鉀(81mg,0.6mmol)溶於10ml乾二烷並脫氣。封閉反應容器並於130℃攪拌加熱混合物5h。冷卻至室溫後,濾除所有固體組分,並將溶液濃縮。殘餘物以管柱層析(環己烷,乙酸乙酯)純化。
MH+:533;1H-NMR(400MHz,CDCl3)δ ppm:9.30(s,1H),8.95(s,1H),8.32(s,1H),8.00(s,1H),7.92(s,1H),3.96(s,3H),3.61-3.56(q,2H),1.21-1.17(t,3H).
於10ml舒倫克(Schlenk)容器中,在氬氣壓下,將2-[3-(乙基磺醯基)-5,6-二氫-4H-環戊[b]噻吩-2-基]-3-甲基-6-(三氟甲基)-3H-咪唑并[4,5-c]吡啶(50mg,0.12mmol)、過氧二硫酸鉀(49mg,0.18mmol)及Selectfluor(氟試劑)(85mg,0.24mmol)溶於1.2ml乙腈及1.2mol水。以血清塞密封容器,並將反應溶液於80℃加熱3h。混合物以二氯甲烷稀釋,且在水-排斥劑濾器上過濾移除水相。移除溶劑後,粗產物以製備型HPLC純化。
在此方法中,除了Ex.I-33,實例化合物I-26、I-27、I-28、I-30也作為副產物單獨分離。
1H-NMR(400MHz,CDCl3)δ ppm:9.10(s,1H),8.19(s,1H),6.10-6.09(m,1H),6.01-6.00(m,1H),3.89(s,3H),3.41-3.32(q,4H),1.25-1.22(t, 3H).
酸性範圍內的LC-MS測定進行於pH 2.7,其使用流動相0.1%甲酸和乙腈水溶液(含0.1%甲酸);從10%乙腈到95%乙腈的線性梯度,儀器:Agilent 1100 LC液相色譜系統,Agilent MSD系統,HTS PAL。
中性範圍內以LC-MS測定M+進行於pH 7.8,其使用流動相0.001莫耳碳酸氫銨水溶液和乙腈;從10%乙腈到95%乙腈的線性梯度。
所選擇實施例之NMR數據以習知形式(δ值、多重峰分裂、氫原子數)或NMR峰列表列出。
在各種情況下,陳述記錄NMR譜的溶劑。
所選擇之實例的1H-NMR數據係以1H-NMR波峰列表形式陳述。對各信號波峰列示先以ppm計之δ值及接著在圓括弧中的信號強度。δ值-不同的信號峰之信號強度值對係以分號彼此分開列示。
一個實施例的波峰列表因此具有下列形式:δ1(強度1);δ2(強度2);........;δi(強度i);......;δn(強度n)
銳利信號的強度與在NMR光譜印出之實例中以公分計之信號高度相關且其顯示真實的信號強度比。在寬信號的例子中,可顯示與光譜中最強的信號相比的數個波峰或中間的信號及其相對強度。
關於1H光譜之化學位移的校準,吾等係使用四甲基矽烷及/或溶劑之化學位移,特別在光譜於DMSO中測量的例子中。因此,四甲基矽烷波峰可能但未必出現在NMR波峰列表中。
1H NMR波峰列表類似於習知的1H NMR印表且因此通常含有在習知的NMR解讀中所列示之所有波峰。
另外,其可如習知的1H NMR印表顯示溶劑信號、標的化合物的立體異構物信號(其同樣由本發明提供)及/或雜質波峰。
在以溶劑及/或水之δ範圍內記述述化合物信號時,吾等的1H NMR波峰列表顯示標準溶劑波峰(例如在D6-DMSO中的DMSO之波峰)及水的波峰,其通常平均具有高強度。
標的化合物的立體異構物波峰及/或雜質的波峰具有平均比標的化合物的波峰(例如具有>90%之純度)更低的強度。
此等立體異構物及/或雜質可為特定的製備方法之典型代表。該等的波峰因此可助於參考「副產物指紋」來辨識吾等製備方法的重現性。
若必要時,以已知的方法(MestreC、ACD模擬,但亦具有憑經驗評估之期望值)計算標的化合物波峰的專家可選擇地使用附加的強度濾波器分離出標的化合物的波峰。此分離法可能類似於習知的1H NMR解讀之相關的波峰擷取。
可在Research Disclosure Database Number 564025中發現1H NMR波峰列表的更多細節。
表1中所列之化合物係如上所述或與其類似地製備。
關於塗佈試管,首先將9mg活性成分溶解於1ml丙酮(p.a.)中,然後以丙酮(p.a.)稀釋至所需的濃度,藉由在軌道振動機轉動和搖動(以30rpm的轉速搖動2小時),將250μl的溶液均勻分佈在內壁及一個25ml玻璃管的底部。如果活性成分溶液含量為900ppm且內部表面積為44.7cm2,均勻分佈,則可達到5μg/cm2的面積劑量。
溶劑蒸發後,將試管中裝滿5-10隻貓蚤(Ctenocephalides felis),用多孔塑料蓋密封,並在室溫和環境濕度下水平放置。48小時後,測定功效。為此,將試管直立並將跳蚤敲擊至試管底部。在底部保持靜止或以不協調的方式移動的跳蚤被認為已經死亡或瀕臨死亡。
如果在該試驗中以5μg/cm2的施用率實現至少80%的功效,則該物質 顯示出對貓櫛頭蚤的良好功效。100%的效力意味著所有的跳蚤已經死亡或瀕臨死亡,0%的效力意味著沒有跳蚤受傷。
在此試驗中,例如,製備實施例中的下列化合物在5μg/cm2(=500g/ha)的施用率下顯示出100%的功效:I-10
溶劑:二甲亞碸
為製造適當之活性成分調配物,將10mg活性成分與0.5ml二甲亞碸混合,並以檸檬酸牛血稀釋獲得所欲濃度。
將約20隻飢餓的貓蚤(Ctenocephalides felis)放入上下用紗布封閉的小室中。以封口膜(parafilm)封閉底部之金屬圓筒置入小室中,該圓筒含有血液/活性成分調配物,其可藉由封口膜供跳蚤吸收。
2天後測定撲殺%,100%意指所有跳蚤皆被撲殺;0%意指沒有跳蚤被撲殺。
在此試驗中,例如,製備實施例中的下列化合物在100ppm施用率下顯示出100%的功效:I-18
在此試驗中,例如,製備實施例中的下列化合物在100ppm施用率下顯示出95%的功效:I-7
在此試驗中,例如,製備實施例中的下列化合物在100ppm施用率下顯示出80%的功效:I-10、I-12
溶劑:二甲亞碸
為製造適當之活性成分調配物,將10mg活性成分與0.5ml二甲亞碸混合,並以水稀釋獲得所欲濃度。
將大約20隻澳大利亞綿羊綠頭蒼蠅幼蟲(Lucilia cuprina)轉移至含有切碎的馬肉及所需濃度的活性成分調配物的試驗容器中。
2天後測定撲殺%,100%意指所有蒼蠅皆被撲殺;0%意指沒有蒼蠅被撲殺。
在此試驗中,例如,製備實施例中的下列化合物在100ppm施用率下顯示出100%的功效:I-1、I-2、I-10
在此試驗中,例如,製備實施例中的下列化合物在20ppm施用率下顯示出90%的功效:I-4
溶劑:二甲亞碸
為製造適當之活性成分調配物,將10mg活性成分與0.5ml二甲亞碸混合,並以水稀釋獲得所欲濃度。
含有以糖溶液及所欲濃度的活性成分調配物處理之海綿的容器中裝入10隻成年家蠅。
2天後測定撲殺%,100%意指所有蒼蠅皆被撲殺;0%意指沒有蒼蠅被撲殺。
在此試驗中,例如,製備實施例中的下列化合物在100ppm施用率下顯示出85%的功效:I-12
在此試驗中,例如,製備實施例中的下列化合物在100ppm施用率下顯示出80%的功效:I-7、I-10、I-18
溶劑:100重量分之丙酮
為製造適當之活性成分調配物,將1重量分之活性成分與所述重量分之溶劑混合,並以水稀釋獲得所欲濃度。
將50μl活性成分配製物移至微量滴定盤並以150μl之IPL41昆蟲培養基(33%+15%糖)加至終體積200μl。之後,各盤以封口膜(parafilm)密封,其中在第二微量滴定盤內之綠桃蚜蟲(Myzus persicae)之混合族群能穿刺該封口膜並吸取溶液。
5天後,測定功效%。100%意指所有蚜蟲已被撲殺;0%意指無蚜蟲被撲殺。
在此試驗中,例如,製備實施例中的下列化合物在0.8ppm施用率下顯示出100%的功效:I-19
在此試驗中,例如,製備實施例中的下列化合物在4ppm施用率下顯示出100%的功效:I-1、I-2、I-3、I-4、I-5、I-8、I-9、I-12、I-15、I-16、I-18、I-20、I-21、I-22、I-23、I-24、I-25
在此試驗中,例如,製備實施例中的下列化合物在4ppm施用率下顯示出90%的功效:I-10、I-11、I-13、I-14
溶劑:78重量分之丙酮1.5重量分之二甲基甲醯胺
乳化劑:烷基芳基聚二醇醚
為配製適當活性成分調配物,將1重量分之活性成分溶於特定重量分之溶劑中,並使用含有1000ppm乳化劑濃度之水加調整至所欲濃度。為製造進一步之試驗濃度,使用含乳化劑之水稀釋調配物。
將被所有階段綠桃蚜蟲(Myzus persicae)侵染之大白菜(Chinese cabbage)(Brassica pekinensis)葉盤以所欲濃度之活性成分調配物噴灑。
5天後,測定功效%。100%意指所有蚜蟲已被撲殺;0%意指無蚜蟲被撲殺。
在此試驗中,例如,製備實施例中的下列化合物在100g/ha施用率下顯示出100%的功效:I-7、I-12、I-18
在此試驗中,例如,製備實施例中的下列化合物在100g/ha施用率下顯示出90%的功效:I-6、I-11、I-14、I-15、I-16、I-21、I-22、I-24、I-25
溶劑:78.0重量分之丙酮1.5重量分之二甲基甲醯胺
乳化劑:烷基芳基聚二醇醚
為製備適當活性成分調配物,將1重量分之活性成分溶於特定重量分之溶劑,並使用含1000ppm乳化劑濃度之水調整至所欲濃度。為製造進一步之試驗濃度,使用含乳化劑之水稀釋調配物。
大白菜(Chinese cabbage)(Brassica pekinensis)葉盤以所欲濃度之活性化合物調配物噴灑並在乾燥後使芥菜甲蟲(Phaedon cochleariae)之幼蟲居住其上。
7天後,測定功效%。100%意指所有甲蟲幼蟲已被撲殺;0%意指無甲蟲幼蟲被撲殺。
在此試驗中,例如,製備實施例中的下列化合物在100g/ha施用率下顯示出100%的功效:I-3、I-7、I-9、I-10、I-12、I-13、I-14、I-18、I-20、I-21
在此試驗中,例如,製備實施例中的下列化合物在100g/ha施用率下顯示出83%的功效:I-11
溶劑:78.0重量分之丙酮 1.5重量分之二甲基甲醯胺
乳化劑:烷基芳基聚二醇醚
為製造適當活性成分調配物,將1重量分之活性成分溶於特定重量分之溶劑中,並以含1000ppm乳化劑濃度之水調整至所欲濃度。為製造進一步之試驗濃度,使用含乳化劑之水稀釋調配物。
玉米(Zea mays)葉盤以所欲濃度之活性成分調配物噴灑並在乾燥後使夜盜蛾(Spodoptera frugiperda)之毛蟲居住其上。
7天後,測定功效%。100%意指所有毛蟲已被撲殺;0%意指無毛蟲被撲殺。
在此試驗中,例如,製備實施例中的下列化合物在100g/ha施用率下顯示出100%的功效:I-3、I-7、I-8、I-9、I-10、I-12、I-13、I-14、I-16、I-18、I-20、I-21、I-23、I-25
溶劑:78.0重量分之丙酮1.5重量分之二甲基甲醯胺
乳化劑:烷基芳基聚二醇醚
為了生產適當的活性化合物調配物,將1重量分的活性化合物溶解在特定重量分之溶劑中,並用含乳化劑濃度為1000ppm的水補足到所需的濃度。為了產生進一步的測試濃度,調配物用含乳化劑的水稀釋。
用所需濃度的活性化合物調配物噴霧受溫室紅蜘蛛蟎(Tetranychus urticae)感染的所有階段的豆葉(Phaseolus vulgaris)葉盤。
6天後,測定功效%。100%意指所有蟎已被撲殺;0%意指無蟎被撲殺。
在此試驗中,例如,製備實施例中的下列化合物在100g/ha施用率下 顯示出90%的功效:I-7、I-12、I-15、I-30
Claims (11)
- 一種式(I)化合物,
其中 代表二個單鍵或一個雙鍵及一個單鍵, 其中, 若 代表雙鍵及單鍵,Aa至Ae因此形成芳香環, Aa 代表氮或碳,Ab 代表氮、氧、硫、N(R 8)或C(R 11),Ac 代表氮、氧、硫或C(R 12),Ad 代表氮、氧、硫、N(R 8)或C(R 13),Ae 代表氮或碳,其中R 8代表(C 1-C 4)-烷基、環丙基或氫,且其中基團Aa、Ab、Ac、Ad及Ae中至多三個可代表氮,且基團Ab、Ac及Ad中至多一個可代表氧或基團Ab、Ac及Ad中至多一個可代表硫或基團Ab及Ad中至多一個可代表N(R 8), 或,在 僅代表單鍵之情況, Aa 代表碳,Ab 代表硫、氧或C(R 11)(R 15),Ac 代表硫、氧或C(R 12)(R 16),且 Ad 代表硫、氧或C(R 13)(R 17),Ae 代表碳,其中基團Aa、Ab、Ac、Ad及Ae中至多一個可代表氧或硫,R 1 代表(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 1-C 6)-氰基烷基、(C 1-C 6)-羥基烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷氧基-(C 1-C 6)-烷基、(C 2-C 6)-烯基、(C 2-C 6)-烯氧基-(C 1-C 6)-烷基、(C 2-C 6)-鹵烯氧基-(C 1-C 6)-烷基、(C 2-C 6)-鹵烯基、(C 2-C 6)-氰基烯基、(C 2-C 6)-炔基、(C 2-C 6)-炔氧基-(C 1-C 6)-烷基、(C 2-C 6)-鹵炔氧基-(C 1-C 6)-烷基、(C 2-C 6)-鹵炔基、(C 2-C 6)-氰基炔基、(C 3-C 8)-環烷基、(C 3-C 8)-環烷基-(C 3-C 8)-環烷基、(C 1-C 6)-烷基-(C 3-C 8)-環烷基、鹵-(C 3-C 8)-環烷基、胺基、(C 1-C 6)-烷基胺基、二-(C 1-C 6)-烷基胺基、(C 3-C 8)-環烷基胺基、(C 1-C 6)-烷基羰基胺基、(C 1-C 6)-烷基硫基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷基亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基羰基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基羰基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基羰基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷氧基羰基-(C 1-C 6)-烷基、(C 1-C 6)-烷基磺醯基胺基、胺基磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基胺基磺醯基-(C 1-C 6)-烷基、二-(C 1-C 6)-烷基胺 基磺醯基-(C 1-C 6)-烷基,或代表(C 1-C 6)-烷基、(C 1-C 6)-烷氧基、(C 2-C 6)-烯基、(C 2-C 6)-炔基、(C 3-C 8)-環烷基,其各可選擇地藉由芳基、雜芳基及雜環基所組成群組之相同或不同之取代基單取代-或多取代,其中芳基、雜芳基或雜環基可各別可選擇地經下列所組成群組之相同或不同之取代基單取代-或多取代:鹵素、氰基、硝基、羥基、胺基、羧基、胺甲醯基、胺基磺醯基、(C 1-C 6)-烷基、(C 3-C 6)-環烷基、(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)-烷基硫亞胺基、(C 1-C 6)-烷基硫亞胺基-(C 1-C 6)-烷基、(C 1-C 6)-烷基硫亞胺基-(C 2-C 6)-烷基羰基、(C 1-C 6)-烷基亞碸醯亞胺基、(C 1-C 6)-烷基亞碸醯亞胺基-(C 1-C 6)-烷基、(C 1-C 6)-烷基亞碸醯亞胺基-(C 2-C 6)-烷基羰基、(C 1-C 6)-烷氧基羰基、(C 1-C 6)-烷基羰基、(C 3-C 6)-三烷基矽烷基及苄基,R 11、R 12、R 13、R 15、R 16、R 17彼此獨立代表氫、氰基、鹵素、硝基、羥基、胺基、三-(C 1-C 6)-烷基矽烷基、(C 3-C 8)-環烷基、(C 3-C 8)-環烷基-(C 3-C 8)-環烷基、(C 1-C 6)-烷基-(C 3-C 8)-環烷基、鹵-(C 3-C 8)-環烷基、(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 1-C 6)-氰基烷基、(C 1-C 6)-羥基烷基、羥基羰基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷氧基羰基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基、(C 2-C 6)-烯基、(C 2-C 6)-鹵烯基、(C 2-C 6)-氰基烯基、(C 2-C 6)-炔基、(C 2-C 6)-鹵炔基、(C 2-C 6)-氰基炔基、(C 1-C 6)-烷氧基、(C 1-C 6)-鹵烷氧基、(C 1-C 6)- 氰基烷氧基、(C 1-C 6)-烷氧基羰基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷基羥基亞胺基、(C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-烷基-(C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-鹵烷基-(C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-烷基硫基、(C 1-C 6)-鹵烷基硫基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基硫基、(C 1-C 6)-烷基硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-鹵烷基亞磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-烷基亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基磺醯基、(C 1-C 6)-鹵烷基磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基磺醯基、(C 1-C 6)-烷基磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基磺醯氧基、(C 1-C 6)-烷基羰基、(C 1-C 6)-烷基硫基羰基、(C 1-C 6)-鹵烷基羰基、(C 1-C 6)-烷基羰氧基、(C 1-C 6)-烷氧基羰基、(C 1-C 6)-鹵烷氧基羰基、胺基羰基、(C 1-C 6)-烷基胺基羰基、(C 1-C 6)-烷基胺基硫基羰基、二-(C 1-C 6)-烷基胺基羰基、二-(C 1-C 6)-烷基胺基硫基羰基、(C 2-C 6)-烯基胺基羰基、二-(C 2-C 6)-烯基胺基羰基、(C 3-C 8)-環烷基胺基羰基、(C 1-C 6)-烷基磺醯基胺基、(C 1-C 6)-烷基胺基、二-(C 1-C 6)-烷基胺基、(C 3-C 8)-環烷基胺基、胺基磺醯基、(C 1-C 6)-烷基胺基磺醯基、二-(C 1-C 6)-烷基胺基磺醯基、(C 1-C 6)-烷基亞碸醯亞胺基、胺基硫基羰基、(C 1-C 6)-烷基胺基硫基羰基、二-(C 1-C 6)-烷基胺基硫基羰基、(C 1-C 6)-烷基羰基胺基(-NHCO-(C 1-C 6)-烷基)、(C 3-C 8)-環烷基羰基胺基、(C 1-C 6)-烷基羰基-(C 1-C 6)-烷基胺基(-N-(C 1-C 6)-烷基-CO-(C 1-C 6)-烷基)、((C 1-C 6)-烷氧基羰基)胺基 (-NHCOO-(C 1-C 6)-烷基)、((C 1-C 6)-烷氧基羰基)-(C 1-C 6)-烷基胺基(-N-(C 1-C 6)-烷基-COO-(C 1-C 6)-烷基)、(C 1-C 6)-烷基胺甲醯氧基(-OCONH-(C 1-C 6)-烷基)、二-(C 1-C 6)-烷基胺甲醯氧基(-OCON-(C 1-C 6)-二烷基)、( N-(C 1-C 6)-烷基胺甲醯基)胺基(-NHCONH-(C 1-C 6)-烷基)、( N,N-二-(C 1-C 6)-烷基胺甲醯基)胺基(-NHCON-(C 1-C 6)-二烷基)、( N-(C 1-C 6)-烷基胺甲醯基)-(C 1-C 6)-烷基胺基(-N-(C 1-C 6)-烷基-CONH-(C 1-C 6)-烷基)、( N,N-二-(C 1-C 6)-烷基胺甲醯基)-(C 1-C 6)-烷基胺基(-N-(C 1-C 6)-烷基-CON-(C 1-C 6)-二烷基)、胺甲醯基胺基(-NHCONH 2)、(胺甲醯基)- N-(C 1-C 6)-烷基胺基(-N-(C 1-C 6)-烷基-CONH 2)或代表芳基或雜芳基,其各可選擇地經相同或不同之取代基單取代-或多取代,其中(在雜芳基之情況下)可選擇地存在至少一個羰基基團,且其中可能之取代基在各情況中如下:氰基、羧基、鹵素、硝基、羥基、胺基、三-(C 1-C 6)-烷基矽烷基、(C 3-C 8)-環烷基、(C 3-C 8)-環烷基-(C 3-C 8)-環烷基、(C 1-C 6)-烷基-(C 3-C 8)-環烷基、鹵-(C 3-C 8)-環烷基、(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 1-C 6)-氰基烷基、(C 1-C 6)-羥基烷基、羥基羰基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷氧基羰基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基、(C 2-C 6)-烯基、(C 2-C 6)-鹵烯基、(C 2-C 6)-氰基烯基、(C 2-C 6)-炔基、(C 2-C 6)-鹵炔基、(C 2-C 6)-氰基炔基、(C 1-C 6)-烷氧基、(C 1-C 6)-鹵烷氧基、(C 1-C 6)-氰基烷氧基、(C 1-C 6)-烷氧基羰基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷基羥基亞胺基、 (C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-烷基-(C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-鹵烷基-(C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-烷基硫基、(C 1-C 6)-鹵烷基硫基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基硫基、(C 1-C 6)-烷基硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-鹵烷基亞磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-烷基亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基磺醯基、(C 1-C 6)-鹵烷基磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基磺醯基、(C 1-C 6)-烷基磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基磺醯氧基、(C 1-C 6)-烷基羰基、(C 1-C 6)-鹵烷基羰基、(C 1-C 6)-烷基羰氧基、(C 1-C 6)-烷氧基羰基、(C 1-C 6)-鹵烷氧基羰基、胺基羰基、(C 1-C 6)-烷基胺基羰基、二-(C 1-C 6)-烷基胺基羰基、(C 2-C 6)-烯基胺基羰基、二-(C 2-C 6)-烯基胺基羰基、(C 3-C 8)-環烷基胺基羰基、(C 1-C 6)-烷基磺醯基胺基、(C 1-C 6)-烷基胺基、二-(C 1-C 6)-烷基胺基、胺基磺醯基、(C 1-C 6)-烷基胺基磺醯基、二-(C 1-C 6)-烷基胺基磺醯基、(C 1-C 6)-烷基亞碸醯亞胺基、胺基硫基羰基、(C 1-C 6)-烷基胺基硫基羰基、二-(C 1-C 6)-烷基胺基硫基羰基、(C 3-C 8)-環烷基胺基或(C 1-C 6)-烷基羰基胺基,其中基團R 11、R 12、R 13、R 15、R 16、R 17中至多二個代表氫以外的取代基,且,在R 11及R 15、R 12及R 16或R 13及R 17皆不代表氫之情況,R 15、R 16及R 17各彼此獨立僅代表氰基、鹵素、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、 鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基或(C 1-C 4)-氰基烷基, 或,在 僅代表單鍵之情況,另R 11及R 15及/或R 13及R 17 在各情況中一起代表氧(=O),Q 代表部分飽和或飽和雜環或雜芳族8-、9-、10-、11-或12-員稠合雙環或三環系統,其可選擇地含至少一個羰基基團,及/或其中該環系統可選擇地經相同或不同之取代基單取代-或多取代,其中該取代基彼此獨立可選自氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C 1-C 6)-烷基矽烷基、鹵-(C 3-C 8)-環烷基、(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 1-C 6)-氰基烷基、(C 1-C 6)-羥基烷基、羥基羰基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷氧基羰基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基、(C 2-C 6)-烯基、(C 2-C 6)-鹵烯基、(C 2-C 6)-氰基烯基、(C 2-C 6)-炔基、(C 2-C 6)-炔氧基-(C 1-C 4)-烷基、(C 2-C 6)-鹵炔基、(C 2-C 6)-氰基炔基、(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)-烷基、(C 2-C 6)-烯氧基-(C 1-C 6)-烷基、(C 2-C 6)-鹵烯氧基-(C 1-C 6)-烷基、(C 1-C 6)-氰基烷氧基、(C 1-C 6)-烷氧基羰基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷基羥基亞胺基、(C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-烷基-(C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-鹵烷基-(C 1-C 6)-烷氧基亞胺基、(C 1-C 6)-烷基硫基、(C 1-C 6)-鹵烷基硫基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基硫基、(C 1-C 6)-烷基硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-鹵烷基亞磺醯基、(C 1-C 6)-烷氧 基-(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-烷基亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基磺醯基、(C 1-C 6)-鹵烷基磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷基磺醯基、(C 1-C 6)-烷基磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷基磺醯氧基、(C 1-C 6)-烷基羰基、(C 1-C 6)-烷基羰基-(C 1-C 6)-烷基、(C 1-C 6)-烷基硫基羰基、(C 1-C 6)-鹵烷基羰基、(C 1-C 6)-烷基羰氧基、(C 1-C 6)-烷氧基羰基、(C 1-C 6)-鹵烷氧基羰基、胺基羰基、(C 1-C 6)-烷基胺基羰基、(C 1-C 6)-烷基胺基硫基羰基、二-(C 1-C 6)-烷基胺基羰基、二-(C 1-C 6)-烷基胺基硫基羰基、(C 2-C 6)-烯基胺基羰基、二-(C 2-C 6)-烯基胺基羰基、(C 3-C 8)-環烷基胺基羰基、(C 1-C 6)-烷基磺醯基胺基、(C 1-C 6)-烷基胺基、二-(C 1-C 6)-烷基胺基、胺基磺醯基、(C 1-C 6)-烷基胺基磺醯基、二-(C 1-C 6)-烷基胺基磺醯基、(C 1-C 6)-烷基亞碸醯亞胺基、胺基硫基羰基、(C 1-C 6)-烷基胺基硫基羰基、二-(C 1-C 6)-烷基胺基硫基羰基、(C 3-C 8)-環烷基胺基、NHCO-(C 1-C 6)-烷基((C 1-C 6)-烷基羰基胺基),或可選擇地經單氰基-取代之(C 3-C 8)-環烷基、(C 3-C 8)-環烷基-(C 3-C 8)-環烷基或(C 1-C 4)-烷基-(C 3-C 8)-環烷基,或其中該取代基彼此獨立可選自苯基及5-或6-員雜芳環,其中苯基及該環可選擇地經選自下列所組成群組之相同或不同之取代基單取代-或多取代:C 1-C 6-烷基、C 2-C 6-烯基、C 2-C 6-炔基、C 3-C 6-環烷基、C 1-C 6-鹵烷基、C 2-C 6-鹵烯基、C 2-C 6-鹵炔基、C 3-C 6-鹵環烷基、鹵素、CN、NO 2、C 1-C 4-烷氧基、C 1-C 4-鹵烷氧基,且 n 代表0、1或2。 - 根據請求項1之式(I)化合物,其特徵在於 在 代表單鍵及雙鍵之情況,且Aa至Ae因此形成芳香環, Aa 代表氮或碳,Ab 代表氮、氧、硫、N(R 8)或C(R 11),Ac 代表氮、氧、硫或C(R 12),Ad 代表氮、氧、硫、N(R 8)或C(R 13),Ae 代表氮或碳,其中R 8代表甲基、乙基、環丙基或氫,且其中基團Aa、Ab、Ac、Ad及Ae中至多三個可代表氮且基團Ab、Ac及Ad中至多一個可代表氧或基團Ab、Ac及Ad中至多一個可代表硫或基團Ab及Ad中至多一個可代表N(R 8), 或,在 僅代表單鍵之情況, Aa 代表碳,Ab 代表硫、氧或C(R 11)(R 15),Ac 代表硫、氧或C(R 12)(R 16),且Ad 代表硫、氧或C(R 13)(R 17),Ae 代表碳,其中基團Aa、Ab、Ac、Ad及Ae中至多一個可代表氧或硫,R 1 代表(C 1-C 4)-烷基、(C 1-C 4)-羥基烷基、(C 1-C 4)-鹵烷基、(C 2-C 4)-烯基、(C 2-C 4)-鹵烯基、(C 2-C 4)-炔基、(C 2-C 4)-鹵炔基、(C 3-C 6)- 環烷基、(C 1-C 4)-烷基硫基-(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基硫基-(C 1-C 4)-烷基、(C 1-C 4)-烷基亞磺醯基-(C 1-C 4)-烷基或(C 1-C 4)-烷基磺醯基-(C 1-C 4)-烷基,R 11、R 12、R 13、R 15、R 16、R 17彼此獨立代表氫、氰基、鹵素、硝基、羥基、胺基、三-(C 1-C 4)-烷基矽烷基、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-氰基烷基、(C 1-C 4)-羥基烷基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷基、(C 2-C 4)-烯基、(C 2-C 4)-鹵烯基、(C 2-C 4)-氰基烯基、(C 2-C 4)-炔基、(C 2-C 4)-鹵炔基、(C 2-C 4)-氰基炔基、(C 1-C 4)-烷氧基、(C 1-C 4)-鹵烷氧基、(C 1-C 4)-氰基烷氧基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷氧基、(C 1-C 4)-烷基羥基亞胺基、(C 1-C 4)-烷氧基亞胺基、(C 1-C 4)-烷基-(C 1-C 4)-烷氧基亞胺基、(C 1-C 4)-鹵烷基-(C 1-C 4)-烷氧基亞胺基、(C 1-C 4)-烷基硫基、(C 1-C 4)-鹵烷基硫基、(C 1-C 4)-烷基硫基-(C 1-C 4)-烷基、(C 1-C 4)-烷基亞磺醯基、(C 1-C 4)-鹵烷基亞磺醯基、(C 1-C 4)-烷基亞磺醯基-(C 1-C 4)-烷基、(C 1-C 4)-烷基磺醯基、(C 1-C 4)-鹵烷基磺醯基、(C 1-C 4)-烷基磺醯基-(C 1-C 4)-烷基、(C 1-C 4)-烷基磺醯氧基、(C 1-C 4)-烷基羰基、(C 1-C 4)-鹵烷基羰基、胺基羰基、胺基硫基羰基、(C 1-C 4)-烷基胺基羰基、二-(C 1-C 4)-烷基胺基羰基、(C 3-C 6)-環烷基胺基羰基、(C 1-C 4)-烷基磺醯基胺基、(C 1-C 4)-烷基胺基、二-(C 1-C 4)-烷基胺基、胺基磺醯基、(C 1-C 4)-烷基胺基磺醯基、二-(C 1-C 4)-烷基胺基磺醯基、胺基硫基羰基、(C 1-C 4)-烷基羰基 胺基、(C 1-C 4)-烷基羰基胺基(-NHCO-(C 1-C 4)-烷基)、(C 3-C 6)-環烷基羰基胺基、(C 1-C 4)-烷基羰基-(C 1-C 4)-烷基胺基(-N-(C 1-C 4)-烷基-CO-(C 1-C 6)-烷基)、((C 1-C 4)-烷氧基羰基)胺基(-NHCOO-(C 1-C 4)-烷基)、((C 1-C 4)-烷氧基羰基)-(C 1-C 4)-烷基胺基(-N-(C 1-C 4)-烷基-COO-(C 1-C 6)-烷基)、(C 1-C 4)-烷基胺甲醯氧基(-OCONH-(C 1-C 4)-烷基)、二-(C 1-C 4)-烷基胺甲醯氧基(-OCON-(C 1-C 4)-二烷基)、( N-(C 1-C 4)-烷基胺甲醯基)胺基(-NHCONH-(C 1-C 4)-烷基)、( N,N-二-(C 1-C 4)-烷基胺甲醯基)胺基(-NHCON-(C 1-C 4)-二烷基)、( N-(C 1-C 4)-烷基胺甲醯基)-(C 1-C 4)-烷基胺基(-N-(C 1-C 4)-烷基-CONH-(C 1-C 4)-烷基)、( N,N-二-(C 1-C 4)-烷基胺甲醯基)-(C 1-C 4)-烷基胺基(-N-(C 1-C 4)-烷基-CON-(C 1-C 4)-二烷基)、胺甲醯基胺基(-NHCONH 2)、(胺甲醯基)- N-(C 1-C 4)-烷基胺基(-N(C 1-C 4)-烷基-CONH 2)或代表苯基或5-或6-員雜芳基,其各可選擇地經相同或不同之取代基單取代-或雙取代,其中(在雜芳基之情況下)可選擇地存在至少一個羰基基團,且該雜原子選自N、S及O,且其中可能的取代基在各情況中如下:氰基、鹵素、乙醯基、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-氰基烷基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷基、(C 2-C 4)-烯基、(C 2-C 4)-炔基、(C 2-(C 1-C 4)-烷氧基、(C 1-C 4)-烷基硫基、(C 1-C 4)-鹵烷基硫基、(C 1-C 4)-烷基硫基-(C 1-C 4)-烷基、(C 1-C 4)-烷基亞磺醯基、 (C 1-C 4)-鹵烷基亞磺醯基、(C 1-C 4)-烷基亞磺醯基-(C 1-C 4)-烷基、(C 1-C 4)-烷基磺醯基、(C 1-C 4)-鹵烷基磺醯基、(C 1-C 4)-烷基磺醯基-(C 1-C 4)-烷基、(C 1-C 4)-烷基磺醯氧基、(C 1-C 4)-烷基羰基、胺基羰基、(C 1-C 4)-烷基胺基羰基、二-(C 1-C 4)-烷基胺基羰基、(C 1-C 4)-烷基磺醯基胺基、胺基磺醯基、(C 1-C 4)-烷基胺基磺醯基、二-(C 1-C 4)-烷基胺基磺醯基或(C 1-C 4)-烷基羰基胺基,其中基團R 11、R 12、R 13、R 15、R 16、R 17中至多二個代表氫以外的取代基,且,在R 11及R 15,R 12及R 16或R 13及R 17皆不代表氫之情況,R 15、R 16及R 17各彼此獨立僅代表氰基、鹵素、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基或(C 1-C 4)-氰基烷基, 或,在 僅代表單鍵之情況,另R 11及R 15及/或R 13及R 17 在各情況中一起較佳地代表氧(=O),Q 代表選自Q1至Q13及Q15至Q21所組成群組之雜芳族9-員或12-員稠合雙環或三環系統,
其中R 4 代表(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-氰基烷基、(C 1-C 4)-羥基烷基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷基、(C 1-C 4)-鹵烷氧基-(C 1-C 4)-烷基、(C 2-C 4)-烯基、(C 2-C 4)-烯氧基-(C 1-C 4)-烷基、(C 2-C 4)-鹵烯氧基-(C 1-C 4)-烷基、(C 2-C 4)-鹵烯基、(C 2-C 4)-氰基烯 基、(C 2-C 4)-炔基、(C 2-C 4)-炔氧基-(C 1-C 4)-烷基、(C 2-C 4)-鹵炔基、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基硫基-(C 1-C 4)-烷基、(C 1-C 4)-烷基亞磺醯基-(C 1-C 4)-烷基、(C 1-C 4)-烷基磺醯基-(C 1-C 4)-烷基或(C 1-C 4)-烷基羰基-(C 1-C 4)-烷基,R 5、R 6 彼此獨立代表氫、氰基、鹵素、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 2-C 4)-烯基、(C 2-C 4)-鹵烯基、(C 2-C 4)-炔基、(C 2-C 4)-鹵炔基、(C 1-C 4)-烷氧基、(C 1-C 4)-鹵烷氧基、(C 1-C 4)-烷氧基亞胺基、(C 1-C 4)-烷基硫基、(C 1-C 4)-鹵烷基硫基、(C 1-C 4)-烷基亞磺醯基、(C 1-C 4)-鹵烷基亞磺醯基、(C 1-C 4)-烷基磺醯基、(C 1-C 4)-鹵烷基磺醯基、(C 1-C 4)-烷基磺醯氧基、(C 1-C 4)-烷基羰基、(C 1-C 4)-鹵烷基羰基、胺基羰基、(C 1-C 4)-烷基胺基羰基、二-(C 1-C 4)-烷基-胺基羰基、(C 1-C 4)-烷基磺醯基胺基、(C 1-C 4)-烷基胺基、二-(C 1-C 4)-烷基胺基、胺基磺醯基、(C 1-C 4)-烷基胺基磺醯基、二-(C 1-C 4)-烷基胺基磺醯基或可選擇地經單氰基-取代之(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基或(C 1-C 4)-烷基-(C 3-C 6)-環烷基,R 7 代表氫、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-氰基烷基、(C 1-C 4)-羥基烷基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷基、(C 1-C 4)-鹵烷氧基-(C 1-C 4)-烷基、(C 2-C 4)-烯基、(C 2-C 4)-烯氧基-(C 1-C 4)-烷基、(C 2-C 4)-鹵烯氧基-(C 1-C 4)-烷基、(C 2-C 4)-鹵烯基、(C 2-C 4)-氰基烯基、(C 2-C 4)-炔基、(C 2-C 4)-鹵炔基、(C 3-C 6)-環烷基、(C 3-C 6)-環 烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基硫基-(C 1-C 4)-烷基、(C 1-C 4)-烷基亞磺醯基-(C 1-C 4)-烷基或(C 1-C 4)-烷基磺醯基-(C 1-C 4)-烷基,且n 代表0、1或2。 - 根據請求項1之式(I)化合物,其特徵在於其對應於式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It),
其中R 1 代表(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基或(C 3-C 6)-環烷基, R 8 代表甲基、乙基、環丙基或氫,R 11、R 12、R 13、R 15、R 16、R 17 彼此獨立代表氫、氰基、鹵素、硝基、羥基、(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷基、(C 1-C 4)-烷氧基、(C 1-C 4)-鹵烷氧基、(C 1-C 4)-烷基硫基、(C 1-C 4)-鹵烷基硫基、(C 1-C 4)-烷基亞磺醯基、(C 1-C 4)-鹵烷基亞磺醯基、(C 1-C 4)-烷基磺醯基、(C 1-C 4)-鹵烷基磺醯基、胺基磺醯基、(C 1-C 4)-烷基胺基磺醯基、二-(C 1-C 4)-烷基胺基磺醯基、胺基羰基、(C 1-C 4)-烷基胺基羰基、二-(C 1-C 4)-烷基胺基羰基、(C 3-C 6)-環烷基胺基羰基、(C 1-C 4)-烷基羰基胺基(-NHCO-(C 1-C 4)-烷基)、(C 3-C 6)-環烷基羰基胺基、(C 1-C 4)-烷基羰基-(C 1-C 4)-烷基胺基(-N-(C 1-C 4)-烷基-CO-(C 1-C 6)-烷基)、((C 1-C 4)-烷氧基羰基)胺基(-NHCOO-(C 1-C 4)-烷基)、( N-(C 1-C 4)-烷基胺甲醯基)胺基(-NHCONH-(C 1-C 4)-烷基)、( N,N-二-(C 1-C 4)-烷基胺甲醯基)胺基(-NHCON-(C 1-C 4)-二烷基)、( N-(C 1-C 4)-烷基胺甲醯基)-(C 1-C 4)-烷基胺基(-N(C 1-C 4)-烷基-CONH-(C 1-C 4)-烷基)、( N,N-二-(C 1-C 4)-烷基胺甲醯基)-(C 1-C 4)-烷基胺基(-N(C 1-C 4)-烷基-CON-(C 1-C 4)-二烷基)、胺甲醯基胺基(-NHCONH 2)、(胺甲醯基)- N-(C 1-C 4)-烷基胺基(-N-(C 1-C 4)-烷基-CONH 2)或特佳地代表苯基、三唑或吡唑、其各可選擇地經相同或不同之取代基單取代-或雙取代,在各情況中可能的取代基為:氰 基、鹵素、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-氰基烷基、(C 2-C 4)-烯基、(C 2-C 4)-炔基、(C 1-C 4)-烷氧基、(C 1-C 4)-烷基硫基、(C 1-C 4)-鹵烷基硫基、(C 1-C 4)-烷基亞磺醯基、(C 1-C 4)-鹵烷基亞磺醯基、(C 1-C 4)-烷基磺醯基、(C 1-C 4)-鹵烷基磺醯基、(C 1-C 4)-烷基磺醯氧基、(C 1-C 4)-烷基羰基、胺基羰基、(C 1-C 4)-烷基胺基羰基、二-(C 1-C 4)-烷基胺基羰基、(C 1-C 4)-烷基磺醯基胺基、胺基磺醯基、(C 1-C 4)-烷基胺基磺醯基、二-(C 1-C 4)-烷基胺基磺醯基或(C 1-C 4)-烷基羰基胺基,其中基團R 11、R 12、R 13、R 15、R 16、R 17中至多或二個代表氫以外的取代基,且,在R 11及R 15、R 12及R 16或R 13或R 17皆不代表氫之情況,R 14、R 15、R 16及R 17各彼此獨立僅代表氰基、鹵素、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基或(C 1-C 4)-鹵烷基,或,在結構式(In)至(It)之情況,R 11及R 15或R 13及R 17另在各情況中一起代表氧(=O),Q 代表選自Q1、Q2、Q3、Q5、Q6、Q8、Q9、Q10、Q12、Q15、Q20及Q21所組成群組之雜芳族9-員稠合雙環環系統, R 4 代表(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-氰基烷基或(C 1-C 4)-烷氧基-(C 1-C 4)-烷基,R 5 代表鹵素、(C 1-C 4)-鹵烷基、(C 1-C 4)-鹵烷氧基、(C 1-C 4)-鹵烷基硫基、(C 1-C 4)-鹵烷基亞磺醯基、(C 1-C 4)-鹵烷基磺醯基或代表可選擇地經單氰基-取代之(C 3-C 6)-環烷基,R 6 代表氫、氰基、鹵素或(C 1-C 4)-烷基,R 7 代表氫、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-氰基烷基、(C 1-C 4)-羥基烷基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷基、(C 1-C 4)-鹵烷氧基-(C 1-C 4)-烷基、(C 2-C 4)-烯基、(C 2-C 4)-烯氧基-(C 1-C 4)-烷基、(C 2-C 4)-鹵烯氧基-(C 1-C 4)-烷基、(C 2-C 4)-鹵烯基、(C 2-C 4)-氰基烯基、(C 2-C 4)-炔基、(C 2-C 4)-鹵炔基、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)- 環烷基、(C 1-C 4)-烷基硫基-(C 1-C 4)-烷基、(C 1-C 4)-烷基亞磺醯基-(C 1-C 4)-烷基或(C 1-C 4)-烷基磺醯基-(C 1-C 4)-烷基,且n 代表0、1或2。 - 根據請求項3之式(Ia)、(Ib)、(Id)、(Ie)、(Ii)至(Ik)、(In)、(Iq)及(Ir)化合物,
其中R 1 代表(C 1-C 4)-烷基、(C 3-C 6)-環烷基或(C 1-C 4)-鹵烷基,R 13、R 15、R 16、R 17 彼此獨立代表氫、鹵素、(C 1-C 4)-鹵烷基或(C 1-C 4)-烷基,R 11、R 12 彼此獨立代表氫、氰基、鹵素、硝基、羥基、(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷基、(C 1-C 4)-烷氧基、(C 1-C 4)-鹵烷氧基、(C 1-C 4)-烷基硫基、(C 1-C 4)-鹵烷基 硫基、(C 1-C 4)-烷基亞磺醯基、(C 1-C 4)-鹵烷基亞磺醯基、(C 1-C 4)-烷基磺醯基、(C 1-C 4)-鹵烷基磺醯基、胺基磺醯基、(C 1-C 4)-烷基胺基磺醯基、二-(C 1-C 4)-烷基胺基磺醯基、胺基羰基、(C 1-C 4)-烷基胺基羰基、二-(C 1-C 4)-烷基胺基羰基、(C 3-C 6)-環烷基胺基羰基、(C 1-C 4)-烷基羰基胺基(-NHCO-(C 1-C 4)-烷基)、(C 3-C 6)-環烷基羰基胺基、(C 1-C 4)-烷基羰基-(C 1-C 4)-烷基胺基(-N-(C 1-C 4)-烷基-CO-(C 1-C 6)-烷基)、((C 1-C 4)-烷氧基羰基)胺基(-NHCOO-(C 1-C 4)-烷基)、( N-(C 1-C 4)-烷基胺甲醯基)胺基(-NHCONH-(C 1-C 4)-烷基)、( N,N-二-(C 1-C 4)-烷基胺甲醯基)胺基(-NHCON-(C 1-C 4)-二烷基)、( N-(C 1-C 4)-烷基胺甲醯基)-(C 1-C 4)-烷基胺基(-N-(C 1-C 4)-烷基-CONH-(C 1-C 4)-烷基)、胺甲醯基胺基(-NHCONH 2)、(胺甲醯基)- N-(C 1-C 4)-烷基胺基(-N(C 1-C 4)-烷基-CONH 2)或代表苯基、吡唑或三唑,其各可選擇地經相同或不同之取代基單取代-或雙取代,在各情況中可能的取代基為:氰基、鹵素、(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-烷氧基、(C 1-C 4)-烷基硫基、(C 1-C 4)-鹵烷基硫基、(C 1-C 4)-烷基亞磺醯基、(C 1-C 4)-鹵烷基亞磺醯基、(C 1-C 4)-烷基磺醯基、(C 1-C 4)-鹵烷基磺醯基、(C 1-C 4)-烷基磺醯氧基、胺基羰基、(C 1-C 4)-烷基胺基羰基、二-(C 1-C 4)-烷基胺基羰基、(C 1-C 4)-烷基羰基胺基,其中基團R 11、R 12、R 13、R 15、R 16、R 17中至多或二個代表氫以外的取 代基,且,在R 11及R 15、R 12及R 16或R 13及R 17皆不代表氫的情況,R 14、R 15、R 16及R 17各彼此獨立僅代表鹵素、(C 1-C 4)-鹵烷基或(C 1-C 4)-烷基,或,在結構式(In)、(Iq)及(Ir)之情況,R 11及R 15或R 13及R 17另在各情況中一起代表氧(=O),Q 代表選自Q1、Q2、Q3、Q5、Q6、Q12、Q10、Q15、Q20及Q21所組成群組之雜芳族9-員稠合雙環環系統 其中R 4 代表(C 1-C 4)-烷基,R 5 代表鹵素、(C 1-C 4)-鹵烷基、(C 1-C 4)-鹵烷氧基、(C 1-C 4)-鹵烷基 硫基、(C 1-C 4)-鹵烷基磺醯基、(C 1-C 4)-鹵烷基亞磺醯基或代表可選擇地經單氰基-取代之(C 3-C 6)-環烷基,R 6 代表氫,R 7 代表氫、(C 1-C 4)-烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-氰基烷基、(C 1-C 4)-烷氧基-(C 1-C 4)-烷基、(C 1-C 4)-鹵烷氧基-(C 1-C 4)-烷基、(C 2-C 4)-烯基、(C 2-C 4)-鹵烯基、(C 2-C 4)-氰基烯基、(C 2-C 4)-炔基、(C 2-C 4)-鹵炔基、(C 3-C 6)-環烷基、(C 3-C 6)-環烷基-(C 3-C 6)-環烷基、(C 1-C 4)-烷基-(C 3-C 6)-環烷基、鹵-(C 3-C 6)-環烷基、(C 1-C 4)-烷基硫基-(C 1-C 4)-烷基、(C 1-C 4)-烷基亞磺醯基-(C 1-C 4)-烷基或(C 1-C 4)-烷基磺醯基-(C 1-C 4)-烷基,且n 代表0、1或2。 - 根據請求項3之式(Ia)、(Id)、(Ij)及(In)化合物,
其中R 1 代表(C 1-C 4)-烷基,R 13 代表氫或鹵素,R 15、R 16、R 17 代表氫,R 11、R 12 彼此獨立代表氫、羥基、氰基、鹵素、(C 1-C 4)-烷基、(C 3-C 6)- 環烷基、(C 1-C 4)-鹵烷基、(C 1-C 4)-鹵烷氧基、胺基羰基、(C 1-C 4)-烷基胺基羰基、二-(C 1-C 4)-烷基胺基羰基、(C 3-C 6)-環烷基胺基羰基、(C 1-C 4)-烷基羰基胺基(-NHCO-(C 1-C 4)-烷基)、(C 3-C 6)-環烷基羰基胺基、( N-(C 1-C 4)-烷基胺甲醯基)胺基(-NHCONH-(C 1-C 4)-烷基)、苯基,或代表吡唑或三唑,其各可選擇地經(C 1-C 4)-烷基、鹵素或(C 1-C 4)-鹵烷基單取代,或,在結構式(In)之情況,R 11及R 15或R 13及R 17另在各情況中一起代表氧(=O),Q 代表Q2、Q3、Q15及Q21所組成群組之雜芳族9-員稠合雙環環系統, R 4 代表(C 1-C 4)-烷基,R 5 代表(C 1-C 4)-鹵烷基、(C 1-C 4)-鹵烷基硫基、(C 1-C 4)-鹵烷基磺醯基、(C 1-C 4)-鹵烷基亞磺醯基或經單氰基-取代之環丙基,R 6 代表氫,及R 7 代表(C 1-C 4)-烷基、環丙基、甲氧基甲基或甲氧基乙基,及n 代表0或2。 - 根據請求項3之式(Ia)、(Id)、(Ij)及(In)化合物,
其中R 1 代表乙基,R 13 代表氫或氟,R 15、R 16、R 17 代表氫,R 11 代表氫、羥基、氰基、環丙基、三氟甲基、溴、碘、氟、胺基羰基、甲基胺基羰基、甲基羰基胺基、環丙基羰基胺基、( N-甲基胺甲醯基)胺基(-NHCONHMe)、苯基、N-甲基吡唑、三氟甲基咪唑或氯吡唑,R 12 代表氫、環丙基、甲基、三氟甲基或氯,或,在結構式(In)之情況,R 11及R 15或R 13及R 17另在各情況中一起代表氧(=O),Q 代表Q2、Q3、Q15及Q21所組成群組之雜芳族9-員稠合雙環環系統, R 4 代表甲基,R 5 代表三氟甲基、三氟甲基磺醯基、三氟甲基硫基、三氟甲基亞磺醯基或五氟乙基,R 6 代表氫, R 7 代表甲基,及n 代表2。 - 根據請求項1至6中任一項之式(I)或(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物,其特徵在於式I(a)、I(b)、I(d)、I(e)、I(g)、I(h)、I(j)或I(k)化合物中至少一個基團R 11或R 12代表非氫之基團。
- 一種農化調配物,其包含根據請求項1至7中任一項之式(I)或(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物及增量劑及/或表面活性劑。
- 根據請求項8之農化調配物,其進一步包含農化活性化合物。
- 一種控制動物害蟲之方法,其特徵在於使根據請求項1至7中任一項之式(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物或根據請求項8或9之農化調配物之作用於動物害蟲及/或其棲地上。
- 一種根據請求項1至7中任一項之式(I)或(Ia)、(Ib)、(Id)、(Ie)、(Ig)至(Ik)及(Im)至(It)化合物或根據請求項8或9之農化調配物用於控制動物害蟲之用途。
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| CN107428743A (zh) | 2015-03-12 | 2017-12-01 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性四环衍生物 |
| ES2779532T3 (es) | 2015-04-08 | 2020-08-18 | Bayer Cropscience Ag | Derivados de imidazo[1,2a]piridin-2-ilo como pesticidas y sus productos intermedios |
| EP3656770A3 (en) | 2015-04-24 | 2020-09-09 | Syngenta Participations AG | Pesticidally active polycyclic derivatives with sulfur substituted five-membered ring heterocycles |
| WO2016169882A1 (en) | 2015-04-24 | 2016-10-27 | Syngenta Participations Ag | Pesticidally active polycyclic derivatives with sulfur substituted five membered ring heterocyles |
| ES2762958T3 (es) * | 2015-07-01 | 2020-05-26 | Syngenta Participations Ag | Derivados tetracíclicos activos como plaguicidas con sustituyentes que contienen azufre |
| WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017125340A1 (de) | 2016-01-22 | 2017-07-27 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
-
2018
- 2018-04-17 MX MX2019012728A patent/MX2019012728A/es unknown
- 2018-04-17 ES ES18718433T patent/ES2923376T3/es active Active
- 2018-04-17 CN CN201880027004.5A patent/CN110582503B/zh active Active
- 2018-04-17 EP EP18718433.8A patent/EP3615540B1/de active Active
- 2018-04-17 US US16/605,815 patent/US20200128830A1/en not_active Abandoned
- 2018-04-17 AU AU2018257372A patent/AU2018257372B2/en not_active Ceased
- 2018-04-17 BR BR112019022273-1A patent/BR112019022273B1/pt active IP Right Grant
- 2018-04-17 WO PCT/EP2018/059727 patent/WO2018197257A1/de not_active Ceased
- 2018-04-17 JP JP2019557364A patent/JP7119001B2/ja active Active
- 2018-04-17 KR KR1020197034062A patent/KR102537983B1/ko active Active
- 2018-04-20 TW TW107113482A patent/TW201839002A/zh unknown
- 2018-04-24 AR ARP180101050A patent/AR111420A1/es not_active Application Discontinuation
- 2018-04-24 UY UY0001037696A patent/UY37696A/es not_active Application Discontinuation
-
2019
- 2019-10-23 PH PH12019502404A patent/PH12019502404A1/en unknown
- 2019-10-24 CO CONC2019/0011754A patent/CO2019011754A2/es unknown
- 2019-10-24 CL CL2019003060A patent/CL2019003060A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| UY37696A (es) | 2018-11-30 |
| CN110582503A (zh) | 2019-12-17 |
| KR20190141202A (ko) | 2019-12-23 |
| BR112019022273A2 (pt) | 2020-06-16 |
| ES2923376T3 (es) | 2022-09-27 |
| KR102537983B1 (ko) | 2023-05-31 |
| CO2019011754A2 (es) | 2020-01-17 |
| JP2020517656A (ja) | 2020-06-18 |
| EP3615540B1 (de) | 2022-04-27 |
| AU2018257372A1 (en) | 2019-11-07 |
| US20200128830A1 (en) | 2020-04-30 |
| JP7119001B2 (ja) | 2022-08-16 |
| AU2018257372B2 (en) | 2022-06-02 |
| CN110582503B (zh) | 2022-05-31 |
| EP3615540A1 (de) | 2020-03-04 |
| AR111420A1 (es) | 2019-07-10 |
| WO2018197257A1 (de) | 2018-11-01 |
| BR112019022273B1 (pt) | 2023-04-11 |
| PH12019502404A1 (en) | 2021-01-25 |
| MX2019012728A (es) | 2020-01-23 |
| CL2019003060A1 (es) | 2020-04-03 |
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