TW201906842A - 用作除害劑之經2-(雜)芳基-取代之稠合雜環衍生物(一) - Google Patents
用作除害劑之經2-(雜)芳基-取代之稠合雜環衍生物(一) Download PDFInfo
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- TW201906842A TW201906842A TW107114385A TW107114385A TW201906842A TW 201906842 A TW201906842 A TW 201906842A TW 107114385 A TW107114385 A TW 107114385A TW 107114385 A TW107114385 A TW 107114385A TW 201906842 A TW201906842 A TW 201906842A
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- Prior art keywords
- alkyl
- spp
- cycloalkyl
- alkoxy
- alkylamino
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- 125000000623 heterocyclic group Chemical group 0.000 title claims description 26
- 239000000575 pesticide Substances 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 257
- 239000000203 mixture Substances 0.000 claims abstract description 137
- 238000009472 formulation Methods 0.000 claims abstract description 103
- 241001465754 Metazoa Species 0.000 claims abstract description 55
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 40
- 239000003905 agrochemical Substances 0.000 claims abstract description 8
- -1 nitro , acetyl Chemical group 0.000 claims description 192
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 134
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 115
- 238000000034 method Methods 0.000 claims description 64
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 45
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 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 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 17
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 17
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 17
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims description 10
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 10
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004606 Fillers/Extenders Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 6
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims description 5
- 239000012868 active agrochemical ingredient Substances 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 5
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 3
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical group N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004770 (C1-C4) haloalkylsulfanyl group Chemical group 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- 125000006802 (C2-C6) alkynylamino group Chemical group 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000005311 halosulfanyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 abstract description 20
- 230000000895 acaricidal effect Effects 0.000 abstract description 12
- 239000000642 acaricide Substances 0.000 abstract description 10
- 239000002917 insecticide Substances 0.000 abstract description 9
- 241000238421 Arthropoda Species 0.000 abstract description 7
- 241000239223 Arachnida Species 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 description 94
- 239000004480 active ingredient Substances 0.000 description 81
- 239000002904 solvent Substances 0.000 description 67
- 238000012360 testing method Methods 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 37
- 239000003995 emulsifying agent Substances 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000003112 inhibitor Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002585 base Substances 0.000 description 26
- 150000003839 salts Chemical class 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 21
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 20
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- 108090000623 proteins and genes Proteins 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
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- 239000002699 waste material Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- JRPGMCRJPQJYPE-UHFFFAOYSA-N zinc;carbanide Chemical compound [CH3-].[CH3-].[Zn+2] JRPGMCRJPQJYPE-UHFFFAOYSA-N 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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- 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
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- 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
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- Agronomy & Crop Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
本發明關於新穎的式(I)之經2-(雜)芳基取代之稠合雜環衍生物,彼等作為用於控制動物害蟲(特別是節肢動物且尤其是昆蟲和蜘蛛)的殺蟎劑及/或殺蟲劑之用途。
具有殺蟲性質之稠合雜環衍生物已描述於文獻例如WO 2010/125985、WO 2014/142292、WO 2014/148451、WO 2016/023954、WO 2016/039441、WO 2016/046071、WO 2016/059145、WO 2016/104746、WO 2016/116338、WO 2015/121136和WO 2017/025419中。
現代的殺蟲劑及殺蟎劑必須符合許多要求,例如關於彼等作用的程度、持續性和範圍及可能用途。毒性、保護有益物種和傳粉者、環境性質、施用率、與其他活性成分或配製物助劑之可組合性的問題扮演一角色,活性成分的合成所涉及的複雜性問題也是如此,且亦可能出現抗藥性,僅僅提及一些參數。單就所有該等原因,而言對於新穎作物保護組成物的尋求不能認為是完成的,且持續需要相較於已知化合物至少在關於個別方面具有改良性質的新穎化合物。
本發明之目的係提供用於控制動物害蟲之化合物,藉由其擴大除害劑在各種方面的範圍。
目前已發現新穎的稠合雙環雜環衍生物,此等具有超越已知化合物之優點,其實例包括更好的生物或環境性質、更廣泛的應用方法、更好的殺蟲或殺蟎作用及與作物植物良好的相容性。稠合雙環雜環衍生物可與用於改良效力(尤其是對抗難以控制的昆蟲)的其他劑組合使用。
此目的及其他未明確說明但可從本文所討論之相關性辨別或衍生之目的因此以新穎式(I)化合物達成
其中(組態1)
A1 為氮、=N+(O-)-或=C(R5)-,A2 為-N(R6)-、氧或硫,R1 為(C1-C6)-烷基、(C1-C6)-鹵烷基、(C1-C6)-氰烷基、(C1-C6)-羥烷基、(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)-氰炔基、(C3-C8)-環烷基、(C3-C6)-鹵環烷基、(C3-C6)-氰環烷基、(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)-烷胺基、二-(C1-C6)-烷胺基、(C3-C8)-環烷胺基、(C1-C6)-烷羰胺基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-鹵烷硫基-(C1-C6)-烷基、(C1-C6)-烷亞磺醯基-(C1-C6)-烷基、(C1-C6)-鹵烷亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷磺醯基-(C1-C6)-烷基、(C1-C6)-鹵烷磺醯基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷磺醯基-(C1-C6)-烷基、(C1-C6)-烷羰基-(C1-C6)-烷基、(C1-C6)-鹵烷羰基-(C1-C6)-烷基、(C1-C6)-烷氧羰基-(C1-C6)-烷基、(C1-C6)-鹵烷氧羰基-(C1-C6)-烷基、(C1-C6)-烷磺醯胺基、胺磺醯基-(C1-C6)-烷基、(C1-C6)-烷胺磺醯基-(C1-C6)-烷基、二-(C1-C6)-烷胺磺醯基-(C1-C6)-烷基, 或在各情況下為視情況相同或不同地經單-或多-芳基-、-雜芳基-或-雜環基-取代之(C1-C6)-烷基、(C1-C6)-烷氧基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C8)-環烷基,其中芳基、雜芳基或雜環基可各自視情況相同或不同地經下列單-或多取代:鹵素、氰基、硝基、羥基、胺基、羧基、胺甲醯基、胺磺醯基、(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)-烷硫基、(C1-C6)-烷亞磺醯基、(C1-C6)-烷磺醯基、(C1-C6)-烷磺亞胺基(alkylsulfimino)、(C1-C6)-烷磺亞胺基-(C1-C6)-烷基、(C1-C6)-烷磺亞胺基-(C2-C6)-烷羰基、(C1-C6)-烷磺醯亞胺基(alkylsulfoximino)、(C1-C6)-烷磺醯亞胺基-(C1-C6)-烷基、(C1-C6)-烷磺醯亞胺基-(C2-C6)-烷羰基、(C1-C6)-烷氧羰基、(C1-C6)-烷羰基、(C3-C6)-三烷矽基或苯甲基,R2 為選自下列之基團:-C(=O)-NR11R12、-C(=S)-NR11R12、-NR11R12、-NR11-C(=O)-R8和-NR11-C(=S)-R8,R3 為C2-鹵烷基,R4 為氫、氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C1-C6)-烷矽基、(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、氰基(C3-C8)-環烷基、(C1-C6)-烷基、(C1-C6)-鹵烷基、(C1-C6)-氰烷基、(C1-C6)-羥烷基、羥羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-鹵烯基、(C2-C6)-氰烯基、(C2-C6)-炔基、(C2-C6)-鹵炔基、(C2-C6)-氰炔基、(C1-C6)-烷氧基、(C1-C6)-鹵烷氧基、(C1-C6)-氰烷氧基、(C1-C6)-烷氧羰基-(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)-烷氧亞胺基、(C1-C6)-烷基-(C1-C6)-烷氧亞胺基、(C1-C6)-鹵烷基-(C1-C6)-烷氧亞胺基、(C1-C6)-烷硫基、(C1-C6)-鹵烷硫基、(C1-C6)-烷氧基-(C1-C6)-烷硫基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷亞磺醯基、(C1-C6)-鹵烷亞磺醯基、(C1-C6)-烷氧基 -(C1-C6)-烷亞磺醯基、(C1-C6)-烷亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷磺醯基、(C1-C6)-鹵烷磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷磺醯基、(C1-C6)-烷磺醯基-(C1-C6)-烷基、(C1-C6)-烷磺醯氧基、(C1-C6)-烷羰基、(C1-C6)-烷硫羰基、(C1-C6)-鹵烷羰基、(C1-C6)-烷羰氧基、(C1-C6)-烷氧羰基、(C1-C6)-鹵烷氧羰基、胺羰基、(C1-C6)-烷胺羰基、(C1-C6)-烷胺硫羰基、二-(C1-C6)-烷胺羰基、二-(C1-C6)-烷胺硫羰基、(C2-C6)-烯胺羰基、二-(C2-C6)-烯胺羰基、(C3-C8)-環烷胺羰基、(C1-C6)-烷磺醯胺基、(C1-C6)-烷胺基、二-(C1-C6)-烷胺基、胺磺醯基、(C1-C6)-烷胺磺醯基、二-(C1-C6)-烷胺磺醯基、(C1-C6)-烷磺醯亞胺基、胺硫羰基、(C1-C6)-烷胺硫羰基、二-(C1-C6)-烷胺硫羰基、(C3-C8)-環烷胺基、NHCO-(C1-C6)-烷基((C1-C6)-烷羰胺基),在各情況下為視情況經單一或多次相同或不同地取代之芳基或雜芳基,其中(在雜芳基的情況下)至少一個羰基可視情況地存在且其中在各情況下可能的取代基如下:氰基、羧基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C1-C6)烷矽基、(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)氰烷基、(C1-C6)羥烷基、羥羰基-(C1-C6)-烷氧基、(C1-C6)烷氧羰基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、(C2-C6)烯基、(C2-C6)鹵烯基、(C2-C6)氰烯基、(C2-C6)炔基、(C2-C6)鹵炔基、(C2-C6)氰炔基、(C1-C6)烷氧基、(C1-C6)鹵烷氧基、(C1-C6)氰烷氧基、(C1-C6)烷氧羰基-(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)烷氧亞胺基、(C1-C6)烷基-(C1-C6)烷氧亞胺基、(C1-C6)鹵烷基-(C1-C6)烷氧亞胺基、(C1-C6)烷硫基、(C1-C6)鹵烷硫基、(C1-C6)烷氧基-(C1-C6)烷硫基、(C1-C6)烷硫基-(C1-C6)烷基、(C1-C6)烷亞磺醯基、(C1-C6)鹵烷亞磺醯基、(C1-C6)烷氧基-(C1-C6)烷亞磺醯基、(C1-C6)烷亞磺醯基-(C1-C6)烷基、(C1-C6)烷磺醯基、(C1-C6)鹵烷磺醯基、(C1-C6)烷氧基-(C1-C6)烷磺醯 基、(C1-C6)烷磺醯基-(C1-C6)烷基、(C1-C6)烷磺醯氧基、(C1-C6)烷羰基、(C1-C6)鹵烷羰基、(C1-C6)烷羰氧基、(C1-C6)烷氧羰基、(C1-C6)鹵烷氧羰基、胺羰基、(C1-C6)烷胺羰基、二-(C1-C6)烷胺羰基、(C2-C6)烯胺羰基、二-(C2-C6)-烯胺羰基、(C3-C8)環烷胺羰基、(C1-C6)烷磺醯胺基、(C1-C6)烷胺基、二-(C1-C6)烷胺基、胺磺醯基、(C1-C6)烷胺磺醯基、二-(C1-C6)烷胺磺醯基、(C1-C6)烷磺醯亞胺基、胺硫羰基、(C1-C6)烷胺硫羰基、二-(C1-C6)烷胺硫羰基、(C3-C8)環烷胺基、(C1-C6)烷羰胺基,R5 為氫、氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C1-C6)-烷矽基、(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)-氰烷基、(C1-C6)-羥烷基、羥羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-鹵烯基、(C2-C6)-氰烯基、(C2-C6)-炔基、(C2-C6)-鹵炔基、(C2-C6)-氰炔基、(C1-C6)-烷氧基、(C1-C6)-鹵烷氧基、(C1-C6)-氰烷氧基、(C1-C6)-烷氧羰基-(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)-烷氧亞胺基、(C1-C6)-烷基-(C1-C6)-烷氧亞胺基、(C1-C6)-鹵烷基-(C1-C6)-烷氧亞胺基、(C1-C6)-烷硫基、(C1-C6)-鹵烷硫基、(C1-C6)-烷氧基-(C1-C6)-烷硫基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷亞磺醯基、(C1-C6)-鹵烷亞磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷亞磺醯基、(C1-C6)-烷亞磺醯基-(C1-C6)-烷基、(C1-C6)-烷磺醯基、(C1-C6)-鹵烷磺醯基、(C1-C6)-烷氧基-(C1-C6)-烷磺醯基、(C1-C6)-烷磺醯基-(C1-C6)-烷基、(C1-C6)-烷磺醯氧基、(C1-C6)-烷羰基、(C1-C6)-烷硫羰基、(C1-C6)-鹵烷羰基、(C1-C6)-烷羰氧基、(C1-C6)-烷氧羰基、(C1-C6)-鹵烷氧羰基、胺羰基、(C1-C6)-烷胺羰基、(C1-C6)-烷胺硫羰基、二-(C1-C6)-烷胺羰基、二-(C1-C6)-烷胺硫羰基、(C2-C6)-烯胺羰基、二-(C2-C6)-烯胺羰 基、(C3-C8)-環烷胺羰基、(C1-C6)-烷磺醯胺基、(C1-C6)-烷胺基、二-(C1-C6)-烷胺基、胺磺醯基、(C1-C6)-烷胺磺醯基、二-(C1-C6)-烷胺磺醯基、(C1-C6)-烷磺醯亞胺基、胺硫羰基、(C1-C6)-烷胺硫羰基、二-(C1-C6)-烷胺硫羰基、(C3-C8)-環烷胺基或-NHCO-(C1-C6)-烷基((C1-C6)-烷羰胺基),R6 為(C1-C6)烷基、(C1-C6)鹵烷基、(C1-C6)氰烷基、(C1-C6)羥烷基、(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、(C1-C6)烷硫基-(C1-C6)烷基、(C1-C6)鹵烷硫基-(C1-C6)烷基、(C1-C6)烷亞磺醯基-(C1-C6)烷基、(C1-C6)鹵烷亞磺醯基-(C1-C6)烷基、(C1-C6)烷磺醯基-(C1-C6)烷基、(C1-C6)鹵烷磺醯基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷硫基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷亞磺醯基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷磺醯基-(C1-C6)烷基、(C1-C6)烷羰基-(C1-C6)烷基、(C1-C6)鹵烷羰基-(C1-C6)烷基、(C1-C6)烷氧羰基-(C1-C6)烷基、(C1-C6)鹵烷氧羰基-(C1-C6)烷基、胺羰基-(C1-C6)烷基、(C1-C6)烷胺基-(C1-C6)烷基、二-(C1-C6)烷胺基-(C1-C6)烷基或(C3-C8)環烷胺基-(C1-C6)烷基,R8 為胺基或在各情況下視情況經單一或多次相同或不同地取代之C1-C4-烷胺基、二-(C1-C4)-烷胺基、C2-C6-烯胺基、C2-C6-炔胺基、C3-C12-環烷胺基、C3-C12-環烷基-(C1-C6)-烷胺基、C4-C12-雙環烷胺基或肼基,其中該等取代基可獨立地選自鹵素、氰基、硝基、羥基、(C=O)OH、C1-C6-烷基、C3-C6-環烷基、C1-C4-烷氧基、C1-C4-鹵烷氧基、C1-C4-烷硫基、C1-C4-烷亞磺醯基、C1-C4-烷磺醯基、C1-C4-鹵烷硫基、C1-C4-鹵烷亞磺醯基、C1-C4-鹵烷磺醯基、C2-C6-烷氧羰基、C2-C6-烷羰基、C1-C6-烷硫羰基、C1-C6- 鹵烷羰基、C1-C6-鹵烷硫羰基、C1-C6-烷羰胺基、胺羰基、C1-C6-烷胺羰基、二-(C1-C6)-烷胺羰基、胺硫羰基、C1-C6-烷胺硫羰基、二-(C1-C6)-烷胺硫羰基、C3-C6-三烷矽基、胺基、C1-C4-烷胺基、二-(C1-C4-烷基)胺基、C3-C6-環烷胺基、胺磺醯基、C1-C6-烷胺磺醯基、二-(C1-C6)-烷胺磺醯基、磺醯胺基、C1-C6-烷磺醯胺基及二-(C1-C6)-烷磺醯胺基,R11、R12 獨立地為氫或在各情況下視情況經單一或多次相同或不同地取代之C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C12-環烷基、C3-C12-環烷基-C1-C6-烷基或C4-C12-雙環烷基,其中該等取代基可獨立地選自鹵素、氰基、硝基、羥基、C1-C6-烷基、C3-C6-環烷基、C1-C4-烷氧基、C1-C4-鹵烷氧基、C1-C4-烷硫基、C1-C4-烷亞磺醯基、C1-C4-烷磺醯基、C1-C4-烷磺亞胺基、C1-C4-烷磺亞胺基-C1-C4-烷基、C1-C4-烷磺亞胺基-C2-C5-烷羰基、C1-C4-烷磺醯亞胺基、C1-C4-烷磺醯亞胺基-C1-C4-烷基、C1-C4-烷磺醯亞胺基-C2-C5-烷羰基、C2-C6-烷氧羰基、C2-C6-烷羰基、C3-C6-三烷矽基、胺基、C1-C4-烷胺基、二-(C1-C4-烷基)胺基、C3-C6-環烷胺基、苯環及3-或6-員芳族部分飽和或飽和的雜環,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自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、氰基、(C=O)OH、CONH2、NO2、OH、C1-C4-烷氧基、C1-C4-鹵烷氧基、C1-C4-烷硫基、C1-C4-烷亞磺醯基、C1-C4-烷磺醯基、C1-C4-鹵烷硫基、C1-C4-鹵烷亞磺醯基、C1-C4-鹵烷磺醯基、C1-C4-烷胺基、二-(C1-C4-烷基)胺基、C3-C6-環烷胺基、(C1-C6-烷基)羰基、(C1-C6-烷氧基)羰基、(C1-C6-烷基)胺羰基、二-(C1-C4-烷基)胺羰基、三-(C1-C2)烷矽基、(C1-C4-烷基)(C1-C4-烷氧基)亞胺基或R11、R12 獨立地為苯環或3-至6-員芳族部分飽和或飽和的雜環,其中該雜原子係選自N、S和O之群組,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代 基可獨立地選自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、氰基、(C=O)OH、CONH2、NO2、OH、C1-C4-烷氧基、C1-C4-鹵烷氧基、C1-C4-烷硫基、C1-C4-烷亞磺醯基、C1-C4-烷磺醯基、C1-C4-鹵烷硫基、C1-C4-鹵烷亞磺醯基、C1-C4-鹵烷磺醯基、C1-C4-烷胺基、二-(C1-C4-烷基)胺基、C3-C6-環烷胺基、(C1-C6-烷基)羰基、(C1-C6-烷氧基)羰基、(C1-C6-烷基)胺羰基、二-(C1-C4-烷基)胺羰基、三-(C1-C2)烷矽基及(C1-C4-烷基)(C1-C4-烷氧基)亞胺基,及n 為0、1或2。
另外已發現式(I)化合物具有作為除害劑(較佳地作為殺蟲劑及/或殺蟎劑)之非常好的效力,且另外通常具有非常好的植物(尤其關於作物植物)相容性。
根據本發明之化合物概括地以式(I)定義。在上文及下文所提及之式中所給出之基團的較佳取代基或範圍係說明如下:
組態2:
A1 較佳為氮、=N+(O-)-或=C(R5)-,A2 較佳為-N(R6)-或氧,R1 較佳為(C1-C4)烷基、(C1-C4)羥烷基、(C1-C4)鹵烷基、(C1-C4)氰烷基、(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)氰烯基、(C2-C4)炔基、(C2-C4)炔氧基-(C1-C4)烷基、(C2-C4)鹵炔氧基-(C1-C4)烷基、(C2-C4)鹵炔基、(C2-C4)氰炔基、(C3-C6)環烷基、(C3-C6)-鹵環烷基、(C3-C6)-氰環烷基、(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)烷胺基、二-(C1-C4)烷胺基、(C3-C6)環烷胺基、(C1-C4)烷羰胺基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)鹵烷硫基-(C1-C4)烷基、(C1-C4)烷亞磺醯基-(C1-C4)烷基、(C1-C4)鹵烷亞磺醯基-(C1-C4)烷基、(C1-C4)烷磺醯基-(C1-C4)烷基、(C1-C4)烷羰基-(C1-C4)烷 基、(C1-C4)鹵烷羰基-(C1-C4)烷基、(C1-C4)烷磺醯胺基,或在各情況下為視情況相同或不同地經單-或二-芳基-、-雜芳基-或-雜環基-取代之(C1-C4)烷基、(C1-C4)烷氧基、(C2-C4)烯基、(C2-C4)炔基、(C3-C6)環烷基,其中芳基、雜芳基或雜環基各自可視情況相同或不同地經下列單-或二取代:鹵素、氰基、胺甲醯基、胺磺醯基、(C1-C4)烷基、(C3-C4)環烷基、(C1-C4)烷氧基、(C1-C4)鹵烷基、(C1-C4)鹵烷氧基、(C1-C4)烷硫基、(C1-C4)烷亞磺醯基、(C1-C4)烷磺醯基、(C1-C4)烷磺亞胺基、或R2 較佳為-C(=O)-NR11R12、-C(=S)-NR11R12、-NR11R12、-NR11-C(=O)-R8或-NR11-C(=S)-R8,R3 較佳為C2-鹵烷基,R4 較佳為氫、氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C1-C4)烷矽基、(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、氰基(C3-C8)-環烷基、(C1-C4)烷基、(C1-C4)鹵烷基、(C1-C4)氰烷基、(C1-C4)羥烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)鹵烯基、(C2-C4)氰烯基、(C2-C4)炔基、(C2-C4)鹵炔基、(C2-C4)氰炔基、(C1-C4)烷氧基、(C1-C4)鹵烷氧基、(C1-C4)氰烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷基羥基亞胺基、(C1-C4)烷氧亞胺基、(C1-C4)烷基-(C1-C4)烷氧亞胺基、(C1-C4)鹵烷基-(C1-C4)烷氧亞胺基、(C1-C4)烷硫基、(C1-C4)鹵烷硫基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷亞磺醯基、(C1-C4)鹵烷亞磺醯基、(C1-C4)烷亞磺醯基-(C1-C4)烷基、(C1-C4)烷磺醯基、(C1-C4)鹵烷磺醯基、(C1-C4)烷磺醯基-(C1-C4)烷基、(C1-C4)烷磺醯氧基、(C1-C4)烷羰基、(C1-C4)鹵烷羰基、胺羰基、胺硫羰基、(C1-C4)烷胺羰基、二-(C1-C4)烷胺羰基、(C1-C4)烷磺醯胺基、(C1-C4)烷胺基、二-(C1-C4)烷胺基、胺磺醯基、(C1-C4)烷胺磺醯基、二-(C1-C4)烷胺磺醯基、胺硫羰基、NHCO-(C1-C4)烷基((C1-C4)烷羰胺基), 及較佳亦為苯基或雜芳基,彼等各自為視情況相同或不同地經單-或二取代,其中(在雜芳基的情況下)至少一個羰基可視情況地存在且其中在各情況下可能的取代基如下:氰基、鹵素、硝基、乙醯基、胺基、(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)氰烷基、(C1-C4)羥烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)鹵烯基、(C2-C4)氰烯基、(C2-C4)炔基、(C2-C4)鹵炔基、(C2-C4)氰炔基、(C1-C4)烷氧基、(C1-C4)鹵烷氧基、(C1-C4)氰烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷基羥基亞胺基、(C1-C4)烷氧亞胺基、(C1-C4)烷基-(C1-C4)烷氧亞胺基、(C1-C4)鹵烷基-(C1-C4)烷氧亞胺基、(C1-C4)烷硫基、(C1-C4)鹵烷硫基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷亞磺醯基、(C1-C4)鹵烷亞磺醯基、(C1-C4)烷亞磺醯基-(C1-C4)烷基、(C1-C4)烷磺醯基、(C1-C4)鹵烷磺醯基、(C1-C4)烷磺醯基-(C1-C4)烷基、(C1-C4)烷磺醯氧基、(C1-C4)烷羰基、(C1-C4)鹵烷羰基、胺羰基、(C1-C4)烷胺羰基、二-(C1-C4)烷胺羰基、(C1-C4)烷磺醯胺基、(C1-C4)烷胺基、二-(C1-C4)烷胺基、胺磺醯基、(C1-C4)烷胺磺醯基、二-(C1-C4)烷胺磺醯基、NHCO-(C1-C4)烷基((C1-C4)烷羰胺基),R5 較佳為氫、氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C1-C4)烷矽基、(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)氰烷基、(C1-C4)羥烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)鹵烯基、(C2-C4)氰烯基、(C2-C4)炔基、(C2-C4)鹵炔基、(C2-C4)氰炔基、(C1-C4)烷氧基、(C1-C4)鹵烷氧基、(C1-C4)氰烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷基羥基亞胺基、(C1-C4)烷氧亞胺基、(C1-C4)烷基-(C1-C4)烷氧亞胺基、(C1-C4)鹵烷基-(C1-C4)烷氧亞胺基、(C1-C4)烷硫基、(C1-C4)鹵烷硫基、(C1-C4)烷硫基 -(C1-C4)烷基、(C1-C4)烷亞磺醯基、(C1-C4)鹵烷亞磺醯基、(C1-C4)烷亞磺醯基-(C1-C4)烷基、(C1-C4)烷磺醯基、(C1-C4)鹵烷磺醯基、(C1-C4)烷磺醯基-(C1-C4)烷基、(C1-C4)烷磺醯氧基、(C1-C4)烷羰基、(C1-C4)鹵烷羰基、胺羰基、胺硫羰基、(C1-C4)烷胺羰基、二-(C1-C4)烷胺羰基、(C1-C4)烷磺醯胺基、(C1-C4)烷胺基、二-(C1-C4)烷胺基、胺磺醯基、(C1-C4)烷胺磺醯基、二-(C1-C4)烷胺磺醯基、胺硫羰基、NHCO-(C1-C4)烷基((C1-C4)烷羰胺基),R6 較佳為(C1-C4)烷基、(C1-C4)鹵烷基、(C1-C4)氰烷基、(C1-C4)羥烷基、(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)烷硫基-(C1-C4)烷基、(C1-C4)鹵烷硫基-(C1-C4)烷基、(C1-C4)烷亞磺醯基-(C1-C4)烷基、(C1-C4)鹵烷亞磺醯基-(C1-C4)烷基、(C1-C4)烷磺醯基-(C1-C4)烷基、(C1-C4)鹵烷磺醯基-(C1-C4)烷基、(C1-C4)烷氧基-(C1-C4)烷硫基-(C1-C4)烷基或(C1-C4)烷羰基-(C1-C4)烷基,R8 較佳為胺基、在各情況下視情況經單一或多次相同或不同地取代之C1-C4-烷胺基、二-(C1-C4)-烷胺基、C2-C6-烯胺基、C2-C6-炔胺基、C3-C12-環烷胺基、C3-C12-環烷基-(C1-C6)-烷胺基、C4-C12-雙環烷胺基或肼基,其中該等取代基可獨立地選自鹵素、氰基、胺基、C1-C6-烷基、C3-C6-環烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷亞磺醯基、C1-C4-烷磺醯基、苯環及3-至6-員芳族部分飽和或飽和的雜環,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自C1-C4-烷基、C1-C4-鹵烷基、鹵素、氰基、NO2、C1-C4-烷氧基或C1-C4-鹵烷氧基,或R11、R12 較佳獨立地為氫、在各情況下視情況經單一或多次相同或 不同地取代之C1-C4-烷基或C3-C6-環烷基,其中該等取代基可獨立地選自鹵素、氰基、苯環及3-至6-員芳族部分飽和或飽和的雜環,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自C1-C4-烷基、C1-C4-鹵烷基、鹵素、氰基、NO2、C1-C4-烷氧基或C1-C4-鹵烷氧基,或R11、R12 較佳獨立地為苯環或3-至6-員芳族部分飽和或飽和的雜環,其中該雜原子係選自N、S、O之群組,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自C1-C4-烷基、C1-C4-鹵烷基、鹵素或氰基,及n 較佳為0、1或2。
組態3:
A1 更佳為氮或=C(R5)-,A2 更佳為-N(R6)-,R1 更佳為(C1-C4)烷基、(C1-C4)羥烷基、(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)烷硫基-(C1-C4)烷基、(C1-C4)烷亞磺醯基-(C1-C4)烷基或(C1-C4)烷磺醯基-(C1-C4)烷基,R2 更佳為-C(=O)-NR11R12、-C(=S)-NR11R12、-NR11R12、-NR11-C(=O)-R8或-NR11-C(=S)-R8,R3 更佳為C2-鹵烷基,R4 更佳為氫、氰基、鹵素、硝基、羥基、胺基、(C3-C6)環烷基、氰基(C3-C8)-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)氰烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)鹵烯基、(C2-C4)氰烯基、(C2-C4)炔基、(C2-C4)鹵炔基、(C2-C4)氰炔基、(C1-C4)烷氧基、(C1-C4)鹵烷氧基、(C1-C4)氰烷氧基、(C1-C4)烷硫基、(C1-C4)鹵烷硫基、(C1-C4) 烷亞磺醯基、(C1-C4)鹵烷亞磺醯基、(C1-C4)烷磺醯基、(C1-C4)鹵烷磺醯基,R5 R5更佳為氫、鹵素、氰基或(C1-C4)烷基,R6 更佳為(C1-C4)烷基或(C1-C4)烷氧基-(C1-C4)烷基,R8 更佳為胺基,在各情況下可視情況地經單-鹵素-、-氰基-、-C1-C4-烷氧基-、-C1-C4-烷硫基-、-C1-C4-烷亞磺醯基-、-C1-C4-烷磺醯基-、-苯基-或-吡啶基-取代之(C1-C4)烷胺基、二-(C1-C4)-烷胺基、(C2-C6)-烯胺基、(C2-C4)-炔胺基、(C3-C6)-環烷胺基、肼基,R11、R12更佳獨立地為氫、在各情況下視情況地經單-鹵素-、-氰基-、-苯基-或-吡啶基-取代之(C1-C4)烷基或(C3-C6)環烷基,及n 更佳為0、1或2。
組態4:
A1 甚至更佳為氮或=C(R5)-,A2 甚至更佳為-N(R6)-,R1 甚至更佳為(C1-C4)烷基、(C1-C4)鹵烷基或(C3-C6)環烷基,R2 甚至更佳為-C(=O)-NR11R12,其中R11、R12甚至更佳各自獨立地為氫、(C1-C4)烷基或(C3-C6)環烷基或R2 甚至更佳為-NR11-C(=O)-R8,其中R8 甚至更佳為(C2-C6)-烯胺基、(C2-C4)-炔胺基、(C3-C6)-環烷胺基、(C1-C4)-烷胺基或肼基及R11 甚至更佳為氫、(C3-C6)環烷基或(C1-C4)烷基,R3 甚至更佳為氟乙基、二氟乙基、三氟乙基、四氟乙基或五氟乙基,R4 甚至更佳為氫、氰基、鹵素、(C1-C4)烷基、(C1-C4)鹵烷基、(C1-C4)鹵烷氧基、(C1-C4)烷硫基、(C1-C4)烷亞磺醯基、(C1-C4)烷磺醯基、(C1-C4)鹵烷硫基、(C1-C4)鹵烷亞磺醯基、(C1-C4)鹵烷磺醯基或(C1-C4)烷羰胺基,R5 甚至更佳為氫、氟、氯、溴或氰基,R6 甚至更佳為甲基、乙基、異丙基、甲氧基甲基或甲氧基乙基 及n 甚至更佳為0、1或2。
組態5:
A1 特別為氮,A2 特別為-NMe,R1 特別為甲基、乙基、正丙基、異丙基或環丙基,R2 特別為-C(=O)-NR11R12,其中R11 特別為氫或(C1-C4)烷基及R12 特別為氫、(C1-C4)烷基或(C3-C6)環烷基,或R2 特別為-NR11-C(=O)-R8,其中R8 特別為(C1-C4)烷胺基或二-(C1-C4)烷胺基及R11 特別為氫或(C1-C4)烷基及R3 特別為五氟乙基或四氟乙基(-CF2CF2H或CFHCF3),R4 特別為氫及n 特別為0或2。
組態6:
A1 尤其為氮,A2 尤其為-NMe,R1 尤其為乙基或甲基,R2 尤其為-C(=O)-NR11R12,其中R11 尤其為氫或甲基及R12 尤其為氫、甲基、環丙基或乙基或R2 尤其為-NR11-C(=O)-R8,其中R8 尤其為甲胺基(-NHMe)、乙胺基(-NHEt)或二甲胺基(-N(Me)2)及R11 尤其為氫或甲基及R3 尤其為五氟乙基,R4 尤其為氫及 n 尤其為2。
較佳者為式(I-1)化合物
其中R1、R2、R3、R4和n係如組態1、組態2、組態3、組態4、組態5或組態6中所定義。
特佳者為式(I-2)化合物
其中R1、R2、R4和n係如組態1、組態2、組態3、組態4、組態5或組態6中所定義。
以下有關式(I)化合物的說明當然也適用於式(I)所包括的式(I-1)和(I-2)之化合物。
強調者為式(I)化合物,其中R1 為(C1-C4)烷基、(C1-C4)鹵烷基或(C3-C6)環烷基及A1、A2、R2、R3、R4、R5、R6、R8、R11、R12和n係如組態1、組態2、組態3、組態5或組態6中所定義。
進一步強調者為式(I)化合物,其中R1 為(C1-C4)烷基及A1、A2、R2、R3、R4、R5、R6、R8、R11、R12和n係如組態1、組態2、組態3、組態4或組態6中所定義。
進一步強調者為式(I)化合物,其中R1 為甲基或乙基 及A1、A2、R2、R3、R4、R5、R6、R8、R11、R12和n係如組態1、組態2、組態3、組態4或組態5中所定義。
進一步強調者為式(I)化合物,其中R1 為甲基及A1、A2、R2、R3、R4、R5、R6、R8、R11、R12和n係如組態1、組態2、組態3、組態4、組態5或組態6中所定義。
進一步強調者為式(I)化合物,其中R1 為乙基及A1、A2、R2、R3、R4、R5、R6、R8、R11、R12和n係如組態1、組態2、組態3、組態4、組態5或組態6中所定義。
進一步強調者為式(I)化合物,其中R2 為-C(=O)-NR11R12,其中R11、R12 在各情形下彼此獨立地為氫、(C1-C4)烷基或(C3-C6)環烷基或R2 為-NR11-C(=O)-R8,其中R8 為(C2-C6)-烯胺基、(C2-C4)-炔胺基、(C3-C6)-環烷胺基、(C1-C4)-烷
胺基或肼基及R11 為氫、(C3-C6)環烷基或(C1-C4)烷基,及A1、A2、R1、R3、R4、R5、R6和n係如組態1、組態2、組態3、組態5或組態6中所定義。
進一步強調者為式(I)化合物,其中R2 為-C(=O)-NR11R12及A1、A2、R1、R3、R4、R5、R6、R11、R12和n係如組態1、組態2、組態3、組態4、組態5或組態6中所定義。
進一步強調者為式(I)化合物,其中R2 為-NR11-C(=O)-R8及A1、A2、R1、R3、R4、R5、R6、R11、R8和n係如組態1、組態2、組態3、組態4、組態5或組態6中所定義。
進一步強調者為式(I)化合物,其中A2 為-NMe 及A1、R1、R2、R3、R4、R5、R8、R11、R12和n係如組態1、組態2、組態3或組態4中所定義。
進一步強調者為式(I)化合物,其中A1 為氮及A2、R1、R2、R3、R4、R6、R8、R11、R12和n係如組態1、組態2、組態3或組態4中所定義。
進一步強調者為式(I)化合物,其中R4 為氫、氰基、鹵素、(C1-C4)烷基、(C1-C4)鹵烷基、(C1-C4)鹵烷氧基、 (C1-C4)烷硫基、(C1-C4)烷亞磺醯基、(C1-C4)烷磺醯基、(C1-C4)鹵烷 硫基、(C1-C4)鹵烷亞磺醯基、(C1-C4)鹵烷磺醯基或(C1-C4)烷羰胺基及A1、A2、R1、R2、R3、R5、R6、R11、R12、R8和n係如組態1、組態2、組態3、組態5或組態6中所定義。
進一步強調者為式(I)化合物,其中R4 為氫及A1、A2、R1、R2、R3、R5、R6、R11、R12、R8和n係如組態1、組態2、組態3或組態4中所定義。
尤其強調者為式(I)化合物,其中R3 為五氟乙基或四氟乙基(-CF2CF2H或CFHCF3)及A1、A2、R1、R2、R4、R5、R6、R11、R12、R8和n係如組態1、組態2、組態3、組態4或組態6中所定義。
尤其進一步強調者為式(I)化合物,其中R3 為五氟乙基及A1、A2、R1、R2、R4、R5、R6、R11、R12、R8和n係如組態1、組態2、組態3、組態4或組態5中所定義。
尤佳為式(I-a)至(I-o)之化合物。
以下有關式(I)化合物的說明當然也適用於式(I)所包括的式(I-1)、(I-2)和(I-a)至(I-o)之化合物。
根據定義,除非另有說明,鹵素係選自氟、氯、溴和碘之群組,依次較佳地選自氟、氯和溴之群組,更佳地選自氟或氯之群組。
在本發明的情況下,除非在別處有不同的定義,否則術語"烷基",其本身或者與其他術語組合,例如鹵烷基,係理解為意指具有具有1至12碳原子且可為分支的或未分支的飽和脂族烴基之基團。C1-C12-烷基的實例為甲基、乙基、正丙基、異丙基、正丁基、異丁基、二級丁基、三級丁基、正戊基、異戊基、新戊基、三級戊基、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,除非在別處有不同的定義,否則術語"烯基",其本身或者與其他術語組合,係理解為意指具有至少一個雙鍵之直鏈或支鏈C2-C12-烯基,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,除非在別處有不同的定義,否則術語"炔基",其本身或者與其他術語組合,係理解為意具有至少一個參鍵之指直鏈或支鏈C2-C12-炔基,例如乙炔基、1-丙炔基和炔丙基。該炔基亦可含有至少一個雙鍵。
根據本發明,除非在別處有不同的定義,否則術語"環烷基",其本身或者與其他術語組合,係理解為意指C3-C8-環烷基,例如環丙基、環丁基、環丙基、環己基、環庚基和環辛基。
術語"烷氧基",其本身或者與其他術語組合,例如鹵烷氧基,在本案中係理解為意指O-烷基,其中術語"烷基"係如上所定義。
鹵素取代之基團(尤其是C2-鹵烷基)係經單-或多鹵化最多至最大可能的取代基數目。在多鹵化的情況下,鹵素原子可為相同或不同。鹵素(Hal)係選自氟、氯、溴和碘之群組,依次較佳地選自氟、氯和溴之群組,更佳地選自氟和氯,且鹵素尤佳為氟。
較佳地,C2-鹵烷基為三-、四-或五鹵化,更佳為四-或五鹵化及最 佳為五鹵化。
C2-鹵烷基較佳包括-CHal2-CHal3、-CHal2-CHal2H、-CHalH-CHal3、-CHal2-CH2Hal、-CH2-CHal3、-CHalH-CHHal2,更佳為-CHal2-CHal3、-CHal2-CHal2H、-CHalH-CHal3且最佳為-CHal2-CHal3。
在此強調者為-CF2-CF3、-CF2-CF2H、-CFH-CF3且最佳強調者為-CF2-CF3。
根據本發明,除非在別處有不同的定義,否則術語"芳基"係理解為意指具有6至14個碳原子的芳族基團,較佳為苯基、萘基、蒽基或菲基,更佳為苯基。
除非在別處有不同的定義,否則術語"芳基烷基"係理解為意指根據本發明定義之"芳基"和"烷基"的組合,其中基團通常係經由烷基鍵結;彼等的實例為苯甲基、苯基乙基或α-甲基苯甲基,特佳者為苯甲基。
除非在別處有不同的定義,否則"雜芳基"表示由碳原子及至少有一個雜原子所組成之單-、雙-或三環雜環基團,其中至少一個環為芳族。較佳地,雜芳基含有3、4、5、6、7或8個碳原子且係選自下列群組: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-苯并二唑基、喹啉基、異喹啉基、啉基、呔基、喹唑啉基、喹啉基、萘啶基、苯并三基、嘌呤基、蝶啶基、咪唑并吡啶基和吲嗪基(indolizinyl)。
除非另有說明,否則視情況地經取代之基團可經單-或多取代,其中取代基在多取代的情況下可為相同或不同。
取決於取代基的性質,式(I)化合物可呈幾何及/或光學活性異構物或不同組成之對應異構物混合物的形式。此等立體異構物為例如鏡像 異構物、非鏡像異構物、阻轉異構物(atropisomers)或幾何異構物。本發明因此包含純立體異構物及此等異構物的任何所欲混合物。
式(I)化合物亦可呈鹽形式,尤其是酸加成鹽及金屬鹽複合物。式(I)化合物及其酸加成鹽及金屬鹽複合物具有良好的效力,尤其用於控制動物害蟲。
通式(I)化合物的適當鹽包括習用無毒鹽,即與適當鹼的鹽和與加入酸的鹽。較佳者為與無機鹼的鹽,諸如鹼金屬鹽(例如鈉、鉀或銫鹽)、鹼土金屬鹽(例如鈣或鎂鹽)、銨鹽、與有機鹼和與無機胺的鹽(例如三乙基銨、二環己基銨,N,N’-二苯甲基乙二銨、吡啶鎓、甲基吡啶銨或乙醇鎓鹽)、與無機酸的鹽(例如鹽酸鹽、氫溴酸鹽、二氫硫酸鹽,三氫硫酸鹽、或磷酸鹽)、與有機羧酸或有機磺酸的鹽(例如甲酸鹽、乙酸鹽、三氟乙酸鹽、馬來酸鹽、酒石酸鹽、甲磺酸鹽、苯磺酸鹽或對甲苯磺酸鹽)、與鹼性胺基酸的鹽(例如精胺酸鹽、天冬胺酸鹽或麩胺酸鹽)、等等。
以通用術語所給出或較佳範圍內所列之基團定義及說明對應地適用於最終產物及適用於起始材料和中間物。此等基團定義可根據需要彼此組合,亦即包括各個較佳範圍之間的組合。
根據本發明較佳者為使用含有上文列示為較佳的意義之組合的式(I)化合物。
根據本發明特佳者為使用含有上文列示為特佳的意義之組合的式(I)化合物。
根據本發明非常特佳者為使用含有上文列示為非常特別佳的定義之組合的式(I)化合物。
根據本發明最佳者為使用含有上文列示為最佳的意義之組合的式(I)化合物。
根據本發明尤其使用的是含有上文列示為尤其強調的意義之組合的式(I)化合物。
方法:
本發明之式(I)化合物可藉由下列流程中所示之方法獲得:
方法A
式(I)化合物可藉由已知方法(例如類似於WO2017/025419中所述之方法)製備。
步驟a)
式(III)化合物可以類似於US5374646或Bioorganic and Medicinal Chemistry Letters 2003,13,1093-1096中所述的方法藉由使式(II)化合物與氨來源在縮合劑存在下反應而製備。式(IV)化合物(其中R6=H和 R5=三氟甲基)之製備係描述於WO 2016/039441中。
式(II)之羧酸為市售或可藉由已知的方法(例如類似於US2010/234604、WO2012/61926或Bioorganic and Medicinal Chemistry Letters,18(2008),5023-5026中所述的方法)製備。
式(II)化合物與氨來源的反應較佳在於現有反應條件下為惰性的習用溶劑中進行。較佳者為醚例如二烷或四氫呋喃。
適當縮合劑為例如羰基二咪唑。
該反應可在減壓下、在大氣壓下或在加壓下進行。較佳地,該反應係在大氣壓力及從20℃至70℃的溫度下進行。
步驟b)
式(V)化合物可類似於WO2017/025419與WO2014/142292中所述的方法藉由使式(III)化合物與式(IV)在鹼性介質中在鈀觸媒存在下反應而製備。
式(IV)化合物可例如類似於WO2014/142292中所述的方法製備。所使用之鈀觸媒可為例如[1,1'-雙-(二苯膦基)二茂鐵]二氯鈀(II)。經常,所使用之鹼為無機鹼諸如三級丁醇鉀。
該反應係在溶劑中進行。經常,使用甲苯。
該反應可在減壓下、在大氣壓力下或在加壓下進行。較佳地,該反應係在大氣壓力及從20至110℃的溫度下進行。
步驟c)
式(VII)化合物可藉由使式(V)化合物與式(VI))化合物在鹼存在下反應而製備。
式(VI)之硫醇衍生物(例如甲硫醇、乙硫醇或異丙硫醇)為市售或可藉由已知的方法(例如類似於US2006/25633、US2006/111591、US2820062、Chemical Communications,13(2000),1163-1164或Journal of the American Chemical Society,44(1922),p.1329中所述的方法)製備。
轉化成式(VII)化合物可以純質或在溶劑中進行,較佳者為在選自於現有反應條件下為惰性的習知溶劑中進行。較佳者為醚,例如二異丙基醚、二烷、四氫呋喃、1,2-二甲氧基乙烷、三級丁基甲基醚; 腈,例如乙腈或丙腈;芳族烴,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-甲基吡咯啶酮或二甲亞碸。
適當鹼之實例為選自由鹼金屬或鹼土金屬的乙酸鹽、磷酸鹽及碳酸鹽所組成之鹼。在此較佳者為碳酸銫、碳酸鈉及碳酸鉀。其他適當鹼為鹼金屬氫化物,例如氫化鈉。
該反應可在減壓下、在大氣壓力下或在加壓下,及在0℃至200℃的溫度下進行。
步驟d)
式(VIII)化合物可藉由氧化式(VII)化合物而製備。該氧化通常是在選自於現有反應條件下為惰性的習知溶劑中進行。較佳者為鹵化烴,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇諸如甲醇或乙醇;甲酸、乙酸、丙酸或水。
適當氧化劑之實例為過氧化氫、間-氯過苯甲酸或過碘酸鈉。
該反應可在減壓下、在大氣壓力下或在加壓下,及在-20℃至120℃的溫度下進行。
步驟e)
式(IX)化合物可藉由氧化式(VIII)化合物而製備。該氧化通常是在溶劑中進行。較佳者為鹵化烴,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇諸如甲醇或乙醇;甲酸、乙酸、丙酸或水。
適當氧化劑之實例為過氧化氫和間-氯過苯甲酸。
該反應可在減壓下、在大氣壓力下或在加壓下,及在-20℃至120℃的溫度下進行。
步驟f)
式(IX)化合物可以一步驟方法藉由氧化式(VII)化合物而製備。該氧化通常是在溶劑中進行。較佳者為鹵化烴,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇例如甲醇或乙醇;甲酸、乙酸、丙酸或水。
適當氧化劑之實例為過氧化氫和間-氯過苯甲酸。
該反應可在減壓下、在大氣壓力下或在加壓下,及在-20℃至120℃的溫度下進行。
步驟g)
式(I')化合物可以一步驟方法藉由類似於Synthesis、(2005)、915-924或Organic Letters、11(2009)、947-950中所述之方法使式(IX)化合物與式(X)化合物反應而製備。
式(X)化合物為市售或可藉由已知的方法(例如類似於Houben-Weyl Methoden der Organischen Chemie volume XVI/2、4th edition中所述的方法)製備。
轉化成式(I')化合物通常係可在溶劑中在鹼存在下進行。較佳溶劑為醚,例如二烷或乙二醇二甲醚;較佳鹼為例如碳酸銫、碳酸鉀或三級丁醇鈉。
轉化成式(I')化合物通常在觸媒和配位基存在下進行。所使用之觸媒可為鈀錯合物,例如參(二苯亞甲基丙酮)二鈀(0)或乙酸鈀,及所用之配位基通常為有機膦化合物,例如雙(二苯膦基)-9,9-二甲基二苯并哌喃(Xanthphos)。
方法B
步驟a)
式(XII)化合物可藉由使式(IX)化合物與式(XI)化合物反應而製備。
式(XI)化合物為市售或可藉由已知的方法製備。
轉化成式(XII)化合物通常是在溶劑中進行。較佳者為醚(例如四氫呋喃、甲基三級丁基醚、二烷、乙二醇二甲醚)、脂族烴(諸如己烷、庚烷)、芳族烴(諸如甲苯、二甲苯)、鹵化烴(例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯)、非質子極性溶劑(例如N,N-二甲基甲醯胺、N-甲基吡咯啶酮、二甲亞碸)、酯(例如乙酸乙酯)、或腈(例如乙腈)。
反應可在鹼存在下進行。適當鹼的實例為含氮雜環諸如吡啶、甲吡啶、2,6-二甲基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯(DBU);三級胺諸如三乙胺及N,N-二異丙基乙胺;無機鹼諸如磷酸鉀、碳酸鉀及氫化鈉。
步驟b)
式化合物(I')可藉由使式(XIII)化合物與式(XII)化合物反應而製備。
式(XIII)化合物為市售或可藉由已知的方法製備。
轉化成式化合物(I')通常是在溶劑中進行。較佳者為醚(例如四氫呋喃、甲基三級丁基醚、二烷、乙二醇二甲醚)、鹵化烴(例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯)、芳族烴(諸如甲苯、二甲苯)、酯(例如乙酸乙酯)、腈(例如乙腈)、非質子極性溶劑(例如N,N-二甲基甲醯胺、N-甲基吡咯啶酮、二甲亞碸)、或含氮雜環諸如吡啶或喹啉。
反應可在縮合劑存在下進行。適當縮合劑的實例為碳化二亞胺諸如1-(3-二甲胺基丙基)-3-乙基碳化二亞胺鹽酸鹽(EDCI)或1,3-二環己基碳化二亞胺。
反應可在適當觸媒存在下進行。適當觸媒的一實例為1-羥基苯并三唑。
式(I')化合物可藉由使式(XIV)化合物與式(XII)化合物反應而製備。
式(XIV)化合物為市售或可藉由已知的方法製備。
轉化成式化合物(I')通常是在溶劑中進行。較佳者為醚(例如四氫呋喃、甲基三級丁基醚、二烷、乙二醇二甲醚)、脂族烴(諸如己烷、 庚烷)、芳族烴(諸如甲苯、二甲苯)、鹵化烴(例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯)、非質子極性溶劑(例如N,N-二甲基甲醯胺、N-甲基吡咯啶酮、二甲亞碸)、酯(例如乙酸乙酯)、或腈(例如乙腈)。
反應可在鹼存在下進行。適當鹼的實例為含氮雜環諸如吡啶、二甲胺基吡啶、甲吡啶、2,6-二甲基吡啶、1,8-二氮雜雙環[5.4.0]-7-十一碳烯(DBU);三級胺諸如三乙胺及N,N-二異丙基乙胺;無機鹼諸如碳酸鉀及氫化鈉。
根據步驟a)及b)之反應也可以從式(VII)化合物或式(VIII)化合物開始。
方法C
基團R1、R3、R4、R6、R11、R12、A1和n具有上述定義;V為(C1-C4)烷基。
步驟a)
式(Ia或Ib)化合物(其中R2為C-鍵結的碳醯胺或硫醯胺)可例如類似於S.A.Vinogradov,D.F.Wilson、Tetrahedron Letters 39(1998),8935-8938藉由式(XV)化合物之羰基化而製備。V基團較佳為甲基、乙基、正丙基或正丁基。可用於該反應的觸媒為鈀磷烷錯合物,例如由氯化鈀、三苯基磷及DPPP(1,3-雙(二苯膦基)丙烷)(1:1:1)所組成之觸媒。較佳的鹼為例如Hünig氏鹼(二異丙基乙胺)或DBU(1,8-二氮雜二環[5.4.0]十一碳-7-烯)。
步驟b、c、d)
式(XVI)之酯最初可使用標準方法(參見DE 2221647)轉化成式(XV)之酸(例如用鹼金屬氫氧化物諸如氫氧化鈉或氫氧化鋰作為鹼,在作為溶劑之醇(例如乙醇或四氫呋喃與水之混合物)中進行。
隨後,式(XVII)之酸係藉由標準方法轉化成式(XVIII)之醯氯,例如使用氯化劑諸如亞硫醯氯或草醯氯。
例如,在稀釋劑諸如二氯甲烷或四氫呋喃中,及例如,在鹼諸如三乙胺或二異丙基乙胺存在下,與式(XIX)之胺的其他反應導致式(Ia)化合物。
式(XIX)化合物為市售或可藉由已知的方法製備。
步驟e)
式(Ib)之硫醯胺可藉由與硫化劑(例如Lawesson氏試劑或P4S10)反應而從式(Ia)之碳醯胺製備。
方法D
步驟a)
類似於方法A步驟a)和b),從式(XXI)化合物而不是從式(III)開始,可能形成式(XXII)化合物。
式(XXI)化合物為市售或可藉由已知的方法製備;參見,例如,European Journal of Medicinal Chemistry,90(2015),170。
步驟b)
式(XXII)化合物可類似於方法A步驟c)轉化成式(XXIII)之硫醚。
步驟c)
式(XXIII)化合物可類似於方法A步驟f)而氧化成式(XXIV)之碸。
步驟d)
如果R11=H和R12=烷基(較佳為甲基)或環烷基或H,則式(XXIV)化合物可藉由與式(XIX)之適當的胺在適當溶劑中及視情況地在觸媒(例如MgCl2)存在下反應而直接轉化成式(Ia)化合物。關於此點參見例 如WO2004/37789、US2003/144278或US2013/35492。
步驟e)
作為步驟d)的替代,式(XXIV)化合物可藉由常識的方法水解成酸(式(XXV)化合物)。
步驟f)
關於從式(XXV)化合物開始而轉化成式(Ia)之醯胺,有多種方法可用。舉例來說可參考用於在縮合劑(例如碳二亞胺諸如1-(3-二甲胺基丙基)-3-乙基碳二亞胺鹽酸鹽(EDCI)或1,3-二環己基碳二亞胺(CDI))及鹼(例如N,N-二甲基吡啶-4-胺(DMAP))存在下從酸製備醯胺之一般標準方法。
方法E
基團R3、R4和R6具有上述定義。X1為鹵素。Y為鹵素或C(=O)OMe。
步驟a)
式(XXVI)化合物可例如類似於Tetrahedron Letters,53(2012),1036-1041,藉由使式(XX)化合物與甲酸反應而製備。
式(XX)化合物可藉由如例如WO 2016/039441和WO 2016/039444中之已知方法製備。
轉化成式(XXVI)化合物通常是如例如Tetrahedron Letters,53(2012),1036-1041和WO 2010/027500中所述在作為溶劑之甲酸中進行,或如WO 2014/091368中所述在原甲酸三乙酯進行。
反應可在減壓下、在大氣壓力下或在加壓下及在0℃至200℃的溫度下進行。。
步驟b)
式(V)化合物可類似於Organic Letters,11(2009),1837-1840藉由使式(XXVI)化合物與式(XXVII)化合物反應而製備。
式(XXVII)化合物及彼等之類似物可藉由類似於Organic Letters,18(2016),5118-5121之已知方法製備。
轉化成式(V)化合物通常是在溶劑中進行。較佳者為醚(例如四氫呋喃、甲基三級丁基醚、二烷、乙二醇二甲醚)、脂族烴(諸如己烷、庚烷)、芳族烴(諸如甲苯、二甲苯)、鹵化烴(例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯)、非質子極性溶劑(例如N,N-二甲基甲醯胺、N-甲基吡咯啶酮、二甲亞碸)、酯(例如乙酸乙酯)、或腈(例如乙腈)。
反應可在鹼存在下進行。適當鹼的實例為市售有機鋅鹼諸如TMPZnCl.LiCl,如Organic Letters,11(2009),1837-1840中所述。
反應也可在鈀化合物或鎳化合物觸媒諸如肆(三苯膦)鈀(0)(縮寫為Pd(PPh3)4)存在下進行。
反應可在減壓下、在大氣壓力下或在加壓下及在0℃至200℃的溫度下進行。
方法F
基團R3、R4、R6、A1、X1和X2具有上述定義。
步驟a)
式(XX)化合物可如WO 2016/039441中所述製備。
式(II)之羧酸為市售或可藉由例如類似於US 2010/234604、WO 2012/061926或Bioorganic and Medicinal Chemistry Letters,18(2008),5023-5026中所述之已知方法製備。
式(II)與(XX)化合物之反應係類似於WO 2016/039441進行。
本發明亦關於控制動物害蟲之方法,其中使式(I)化合物作用於動物害蟲及/或其棲息地。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。此較佳地排除用於人體或動物體的手術或治療處理之方法及在人體或動物體上進行之診斷方法。
本發明此外關於式(I)化合物作為除害劑(尤其是作物保護組成物)之用途。
在本申請案的情況下,術語"除害劑"在各情況下亦總是包含術語"作物保護組成物"。
產生良好的植物耐受性、有利的溫血動物毒性及良好的環境相容性(compatibility)的式(I)化合物適合於保護植物及植物組織對抗生物或非生物脅迫因子、適合於增加收成產率、適合於改良收成材料的品質和適合於控制農業、園藝、畜牧業、水產培養、森林、花園和休閒設施、庫存產品與材料的保護、及衛生防區中所遇到的動物害蟲,尤其是昆蟲、蜘蛛、蠕蟲、尤其是線蟲和軟體動物。
在本專利申請案的情況下,術語“衛生”應理解為意指目的是預防疾病(其是傳染性疾病)且用以保護人類及動物健康及/或保護環境及/或維持清潔的任何及所有措施、防備及程序。根據本發明,這尤其包括用於例如紡織品或硬質表面(尤其是玻璃、木材、混凝土、瓷器、陶瓷、塑料或者金屬的表面)之清潔、消毒及滅菌以確保該等保持無衛生害蟲及/或彼等糞便的措施。關於此點本發明之保護範圍較佳地排除欲應用於人體或動物體的手術或治療處理程序及在人體或動物體上進行之診斷程序。
術語“衛生防區”涵蓋其中該等衛生措施、防備及程序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、馬厩、動物飼養等等中的衛生。
術語"衛生害蟲"因此應理解為意指一或多種存在於衛生防區是有問題的動物害蟲,尤其是出於健康的理由。主要目標因此為將衛生害蟲之存在及/或衛生害蟲暴露於衛生防區中予以避免或限制至最低程度。這尤其可透過使用除害劑而達成,可使用該等除害劑同時防止侵襲及 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配製物。衛生害蟲包括例下述有機體。
術語“衛生保護”因此涵蓋藉其可維持及/或改良此等衛生措施、防備及程序的所有行動。
式(I)化合物較佳地可用作為除害劑。彼等具有對抗一般敏感及抗性物種且亦對抗所有或一些發育期之活性。上述害蟲包括:來自節肢動物門(Arthropoda)之害蟲,特別為來自蜘蛛綱(Arachnida)例如粉蟎屬(Acarus spp.)(例如粗腳粉蟎(Acarus siro)、枸杞瘤節蜱(Aceria kuko)、柑橘瘤癭蟎(Aceria sheldoni))、剌皮節蜱屬(Aculops spp.)、刺節蜱屬(Aculus spp.)(例如福氏刺節蜱(Aculus fockeui)、蘋果刺節蜱(Aculus schlechtendali))、大壁蝨屬(Amblyomma spp.)、橫紋葉蟎(Amphitetranychus viennensis)、銳緣壁蝨屬(Argas spp.)、牛尾壁蝨屬(Boophilus spp.)、短須蟎屬(Brevipalpus spp.)(例如紫紅短須蟎(Brevipalpus phoenicis))、麥苔蟎(Bryobia graminum)、苜蓿苔蟎(Bryobia praetiosa)、刺尾蠍屬(Centruroides spp.)、足蟎屬(Chorioptes spp.)、雞蟎(Dermanyssus gallinae)、歐洲室塵蟎(Dermatophagoides pteronyssinus)、美洲塵蟎(Dermatophagoides farinae)、革蜱屬(Dermacentor spp.)、始葉蟎屬(Eotetranychus spp.)(例如核桃始葉蟎(Eotetranychus hicoriae))、梨上節蜱(Epitrimerus pyri)、真葉蟎屬(Eutetranychus spp.)(例如班氏真葉蟎(Eutetranychus banksi))、節蜱屬(Eriophyes spp.)(例如梨節蜱(Eriophyes pyri))、家食甜蟎(Glycyphagus domesticus)、紅足海鐮螯蟎(Halotydeus destructor)、半跗線蟎屬(Hemitarsonemus spp.)(例如茶半跗線蟎(Hemitarsonemus latus)(=多食細蟎(Polyphagotarsonemus latus))、長鬚壁蝨屬(Hyalomma spp.)、硬蜱屬(Ixodes spp.)、寡婦蜘蛛屬(Latrodectus spp.)、棕蜘蛛屬(Loxosceles spp.)、歐洲秋收恙蟎(Neutrombicula autumnalis)、奴合撒屬(Nuphersa spp.)、赤葉蟎屬(Oligonychus spp.)(例如茶紅葉蟎(Oligonychus coffeae)、柏木赤葉蟎(Oligonychus coniferarum)、冬青赤葉蟎(Oligonychus ilicis)、甘蔗赤葉蟎(Oligonychus indicus)、芒果赤葉蟎(Oligonychus mangiferus)、草地赤葉蟎(Oligonychus pratensis)、石榴赤葉蟎(Oligonychus punicae)、樟赤葉蟎(Oligonychus yothersi))、鈍 緣蜱屬(Ornithodorus spp.)、禽刺蟎屬(Ornithonyssus spp.)、葉蟎屬(Panonychus spp.)(例如柑橘葉蟎(Panonychus citri)(=柑橘全爪蟎(Metatetranychus citri)、歐洲葉蟎(Panonychus ulmi)(=Metatetranychus ulmi)、柑橘銹蟎(Phyllocoptruta oleivora)、多趾寬葉蟎(Platytetranychus multidigituli)、多食細蟎(Polyphagotarsonemus latus)、痂恙蟲屬(Psoroptes spp.)、扇頭壁蝨屬(Rhipicephalus spp.)、根蟎屬(Rhizoglyphus spp.)、疥癬蟲屬(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 confuses)、白跗線蟎(Tarsonemus pallidus))、葉蟎屬(Tetranychus spp.)(例如加拿大葉蟎(Tetranychus canadensis)、朱砂葉蟎(Tetranychus cinnabarinus)、土耳其斯坦葉蟎(Tetranychus turkestani)、二點葉蟎(Tetranychus urticae))、阿氏真恙蟎(Trombicula alfreddugesi)、蠍屬(Vaejovis spp.)、斜背瘤節蜱(Vasates lycopersici);來自唇足綱(Chilopoda)之綱,例如地蜈蚣屬(Geophilus spp.)、蚰蜒屬(Scutigera spp.);來自黏管目(Collembola)之目或綱,例如棘跳蟲(Onychiurus armatus);綠圓跳蟲(Sminthurus viridis);來自倍足綱(Diplopoda)之綱,例如具斑馬陸(Blaniulus guttulatus);來自昆蟲綱(Insecta)之綱,例如來自蜚蠊目(Blattodea)之目,例如東方蜚蠊(Blatta orientalis)、亞洲蜚蠊(Blattella asahinai)、德國蜚蠊(Blattella germanica)、馬德拉蜚蠊(Leucophaea maderae)、歐洲缺翅姬蜚蠊(Loboptera decipiens)、家屋斑蠊(Neostylopyga rhombifolia)、角腹蠊屬(Panchlora spp.)、稀蠊屬(Parcoblatta spp.)、家蠊屬(Periplaneta spp.)(例如美洲家蠊(Periplaneta americana)、澳洲家蠊(Periplaneta australasiae))、蘇利南潛蠊(Pycnoseelus surinamensis)、棕帶姬蠊(Supella longipalpa);來自鞘翅目(Coleoptera)之目,例如條紋葉甲(Acalymma vittatum)、菜豆象(Acanthoscelides obtectus)、褐金龜屬(Adoretus spp.)、小蜂窩甲蟲(Aethina tumida)、赤楊紫跳甲(Agelastica alni)、瘦吉丁蟲屬(Agrilus spp.)(例如光蠟瘦吉丁蟲(Agrilus planipennis)、吉丁蟲(Agrilus coxalis)、 線紋瘦吉丁蟲(Agrilus bilineatus)、青銅樺吉丁蟲(Agrilus anxius))、叩甲屬(Agriotes spp.)(例如直條叩甲(Agriotes linneatus)、小麥叩甲(Agriotes mancus)、外米擬步行蟲(Alphitobius diaperinus)、六月金龜子(Amphimallon solstitialis)、家具竊蠹(Anobium punctatum)、星天牛屬(Anoplophora spp.)(例如光肩星天牛(Anoplophora glabripennis))、花象屬(Anthonomus spp.)(例如棉鈴象甲(Anthonomus grandis))、圓皮囊屬(Anthrenus spp.)、梨象屬(Apion spp.)、甘蔗金龜屬(Apogonia spp.)、隱食甲屬(Atomaria spp.)(例如甜菜隱食甲(Atomaria linearis))、毛皮囊屬(Attagenus spp.)、天藍巴利斯(Baris caerulescens)、惡條豆象(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.)、菜豆螢葉甲(Cerotoma trifurcata)、象甲屬(Ceutorrhynchus spp.)(例如甘藍莢象甲(Ceutorrhynchus assimilis)、油菜莖象甲(Ceutorrhynchus quadridens)、蕪菁象甲(Ceutorrhynchus rapae))、凹脛跳甲屬(Chaetocnema spp.)(例如甘薯凹脛跳甲(Chaetocnema confinis)、玉米葉凹脛跳甲(Chaetocnema denticulata)、荒地玉米跳甲(Chaetocnema ectypa))、門第庫斯方喙象(Cleonus mendicus)、寬胸金針蟲屬(Conoderus spp.)、根頸象屬(Cosmopolites spp.)(例如香蕉根頸象(Cosmopolites sordidus))、新西蘭肋翅腿金龜(Costelytra zealandica)、叩甲屬(Ctenicera spp.)、象鼻蟲屬(Curculio spp.)(例如美核桃象鼻蟲(Curculio caryae))、大栗象鼻蟲(Curculio caryatrypes)、栗鈍象鼻蟲(Curculio obtusus)、小栗象鼻蟲(Curculio sayi)、鏽赤扁穀盜(Cryptolestes ferrugineus)、長角扁穀盜(Cryptolestes pusillus)、楊幹隱喙象(Cryptorhynchus lapathi)、芒果隱喙象(Cryptorhynchus mangiferae)、細枝象屬(Cylindrocopturus spp.)、密點細枝象(Cylindrocopturus adspersus)、洋松細枝象(Cylindrocopturus furnissi)、大小蠹屬(Dendroctonus spp.)(例如山松甲蟲(Dendroctonus ponderosae))、皮囊屬(Dermestes spp.)、葉甲屬(Diabrotica spp.)(例如黃瓜條葉甲(Diabrotica balteata)、玉米根葉甲(Diabrotica barberi)、十一星葉甲食根亞種(Diabrotica undecimpunctata howardi)、十一星瓜葉甲幼蟲(Diabrotica undecimpunctata undecimpunctata)、玉米根螢葉甲(Diabrotica virgifera virgifera)、墨西哥玉米根葉甲(Diabrotica virgifera zeae)、蛀野螟屬(Dichocrocis spp.)、稻鐵甲蟲(Dicladispa armigera)、兜蟲屬(Diloboderus spp.)、象甲屬(Epicaerus spp.)、食植瓢蟲屬(Epilachna spp.)(例如南瓜食植瓢蟲(Epilachna borealis)、墨西哥豆食植瓢蟲(Epilachna varivestis))、毛跳甲屬(Epitrix spp.)(例如黃瓜毛跳甲(Epitrix cucumeris)、茄毛跳甲(Epitrix fuscula)、煙草毛跳甲(Epitrix hirtipennis)、美國馬鈴薯毛跳甲(Epitrix subcrinita)、塊莖毛跳甲(Epitrix tuberis))、鑽孔蟲屬(Faustinus spp.)、裸蛛甲(Gibbium psylloides)、闊角穀盜(Gnathocerus cornutus)、菜心野螟(Hellula undalis)、黑異爪蔗金龜(Heteronychus arator)、寡節鰓金龜屬(Heteronyx spp.)、優雅海拉莫法(Hylamorpha elegans)、家天牛(Hylotrupes bajulus)、苜蓿葉象甲(Hypera postica)、金象甲(Hypomeces squamosus)、咪小蠹屬(Hypothenemus spp.)(例如咖啡果咪小蠹(Hypothenemus hampei)、蘋枝褐咪小蠹(Hypothenemus obscurus)、柔毛咪小蠹(Hypothenemus pubescens))、甘蔗大褐齒爪鰓金龜(Lachnosterna consanguinea)、鋸角毛食骸甲(Lasioderma serricorne)、長首穀盜(Latheticus oryzae)、薪甲屬(Lathridius spp.)、細頸金花蟲屬(Lema spp.)、科羅拉多金花蟲(Leptinotarsa decemlineata)、銀潛蛾屬(Leucoptera spp.)(例如咖啡銀潛蛾(Leucoptera coffeella))、Limonius ectypus、水稻水象鼻蟲(Lissorhoptrus oryzophilus)、蔔象屬(Listronotus)(=象甲屬(Hyperodes spp.))、筒喙象屬(Lixus spp.)、螢葉甲屬(Luperodes spp.)、黃胸寡毛跳甲(Luperomorpha xanthodera)、粉蠹屬(Lyctus spp.)、縊虎天牛屬(Megacyllene spp.)(例如刺槐天牛(Megacyllene robiniae))、美洲葉甲屬(Megascelis spp.)、梳爪叩甲屬(Melanotus spp.)(Melanotus longulus oregonensis)、花粉甲(Meligethes aeneus)、鰓金龜屬(Melolontha spp.)(例如大栗鳃角金龟(Melolontha melolontha))、Migdolus屬、長角天牛屬(Monochamus spp.)、南美果樹象甲(Naupactus xanthographus)、郭公蟲屬(Necrobia spp.)、Neogalerucella屬、金黃蛛甲(Niptus hololeucus)、椰子犀角金龜(Oryctes rhinoceros)、鋸胸粉扁蟲(Oryzaephilus surinamensis)、Oryzaphagus oryzae、耳喙象屬(Otiorrhynchus spp.)(例如蘋果耳喙象(Otiorhynchus cribricollis)、苜蓿耳 喙象(Otiorhynchus ligustici)、草莓耳喙象(Otiorhynchus ovatus)、草莓根耳喙象(Otiorhynchus rugosostriarus)、葡萄黑耳喙象(Otiorhynchus sulcatus))、負泥蟲屬(Oulema spp.)(例如黑角負泥蟲(Oulema melanopus)、稻負泥蟲(Oulema oryzae)、小青花金龜(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.)(例如辣根葉蚤(Phyllotreta armoraciae)、油菜籽葉蚤(Phyllotreta pusilla)、西部葉蚤(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.)、大谷蠹(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.)、暗色瓢蟲(Rhizobius ventralis)、穀蠹(Rhizopertha dominica)、棕櫚象屬(Rhynchophorus spp.)、紅棕象甲(Rhynchophorus ferrugineus)、棕櫚象甲(Rhynchophorus palmarum)、小蠹屬(Scolytus spp.)(例如歐洲榆小蠹(Scolytus multistriatus))、六齒長蠹蟲(Sinoxylon perforans)、米象屬(Sitophilus spp.)(例如穀象蟲(Sitophilus granarius)、羅望子象(Sitophilus linearis)、米象(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.)、纖毛象屬(Tanymecus spp.)(例如玉米纖毛象(Tanymecus dilaticollis)、印度纖毛象(Tanymecus indicus)、甜菜灰色象蟲(Tanymecus palliatus)、)、大黃粉蟲(Tenebrio molitor)、大穀盜(Tenebrioides mauretanicus)、擬穀盜屬(Tribolium spp.)(例如美洲黑擬穀盜(Tribolium audax)、擬穀盜(Tribolium castaneum)、扁擬穀盜(Tribolium confusum)、斑皮蠹屬(Trogoderma spp.)、籽象屬(Tychius spp.)、脊虎天牛屬(Xylotrechus spp.)、距步甲屬(Zabrus spp.),例如玉米距步甲(Zabrus tenebrioides);來自革翅目(Dermaptera)之目,例如海肥螋(Anisolabis maritime)、歐洲秋螋(Forficula auricularia)、溪岸蠼螋(Labidura riparia);來自雙翅目(Diptera)之目,例如斑蚊屬(Aedes spp.)(例如埃及斑蚊 (Aedes aegypti))、白線斑蚊(Aedes albopictus)、叮刺斑蚊(Aedes sticticus)、白肋斑蚊(Aedes vexans),潛蠅屬(Agromyza spp.)(例如苜蓿斑潛蠅(Agromyza frontella)、玉米斑潛蠅(Agromyza parvicornis))、果實蠅屬(Anastrepha spp.)、瘧蚊屬(Anopheles spp.)(例如四斑瘧蚊(Anopheles quadrimaculatus)、岡比亞瘧蚊(Anopheles gambiae)),瘿蚊屬(Asphondylia spp.)、寡毛實蠅屬(Bactrocera spp.)(例如瓜實蠅(Bactrocera cucurbitae)、東方果實蠅(Bactrocera dorsalis)、橄欖實蠅(Bactrocera oleae)),花園毛蚊(Bibio hortulanus)、琉璃蠅(Calliphora erythrocephala)、紅頭麗蠅(Calliphora vicina)、地中海果實蠅(Ceratitis capitata)、搖蚊屬(Chironomus spp.)、金蠅屬(Chrysomya spp.)、斑虻屬(Chrysops spp.)、高額麻虻(Chrysozona pluvialis)、螺旋蠅屬(Cochliomya 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))、人皮蠅(Cordylobia anthropophaga)、稻環搖蚊(Cricotopus sylvestris)、家蚊屬(Culex spp.)(例如地下家蚊(Culex pipiens)、熱帶家蚊(Culex quinquefasciatus))、庫蠓屬(Culicoides spp.)、絨蚊屬(Culiseta spp.)、野生齧齒蠅屬(Cuterebra spp.)、橄欖蠅(Dacus oleae)、葉癭蚊屬(Dasineura spp.)(例如油菜莢葉癭蚊(Dasineura brassicae))、地種蠅屬(Delia spp.)(例如蔥地種蠅(Delia antiqua)、麥地種蠅(Delia coarctata)、毛跗地種蠅(Delia florilega)、灰地種蠅(Delia platura)、甘藍地種蠅(Delia radicum))、人膚蠅(Dermatobia hominis)、果蠅屬(Drosophila spp.)(例如黑腹果蠅(Drosophila melanogaster)、斑翅果蠅(Drosophila suzukii))、稻象屬(Echinocnemus spp.)、芹菜尤列實蠅(Euleia heraclei)、廁蠅屬(Fannia spp.)、馬蠅屬(Gasterophilus spp.)、舌蠅屬(Glossina spp.)、麻虻屬(Haematopota spp.)、毛眼水蠅屬(Hydrellia spp.)、小灰毛眼水蠅(Hydrellia griseola)、種蠅屬(Hylemya spp.)、蝨蠅屬(Hippobosca spp.)、牛蠅屬(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))、羅蛉屬(Lutzomyia spp.)、 孟松蚊屬(Mansonia spp.)、家蠅屬(Musca spp.)(例如家蠅(Musca domestica)、舍蠅(Musca domestica vicina))、狂蠅屬(Oestrus spp.)、黑麥稈蠅(Oscinella frit)、擬長跗搖蚊屬(Paratanytarsus spp.)、Paralauterborniella sucincta、花蠅屬(Pegomya)或泉蠅屬(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.)、玻璃蠅屬(Phormia spp.)、鎧氏酪蠅(Piophila casei)、蘆筍實蠅(Platyparea poeciloptera)、Prodiplosis屬、胡蘿蔔莖蠅(Psila rosae)、繞實蠅屬(Rhagoletis spp.)(例如櫻桃繞實蠅(Rhagoletis cingulata)、核桃繞實蠅(Rhagoletis completa)、黑櫻桃繞實蠅(Rhagoletis fausta)、西部櫻桃繞實蠅(Rhagoletis indifferens)、越桔繞實蠅(Rhagoletis mendax)、蘋果繞實蠅(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.)、根斑蠅屬(Tetanops spp.)、大蚊屬(Tipula spp.)(例如歐洲大蚊(Tipula paludosa)、牧場大蚊(Tipula simplex)、番木瓜長尾實蠅(Toxotrypana curvicauda);來自半翅目(Hemiptera)之目,例如Acizzia acaciaebaileyanae、Acizzia dodonaeae、Acizzia uncatoides、Acrida turrita、無網長管蟲牙屬(Acyrthosipon spp.)(例如豌豆蟲牙(Acyrthosiphon pisum))、Acrogonia屬、Aeneolamia屬、隆脉木蝨屬(Agonoscena 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)、圓蚧屬(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))、蚜蟲屬(Aphis spp.)(例如橘卷菜蚜(Aphis citricola)、豆蚜(Aphis craccivora)、蠶豆蚜(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)、葡萄葉蟬(Arboridia apicalis)、Arytainilla屬、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))、Atanus屬、馬鈴薯蚜(Aulacorthum solani)、煙草粉蝨(Bemisia tabaci)、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))、小褐稻蝨(Calligypona marginata)、Capulinia屬、紅頭大葉蟬(Carneocephala fulgida)、甘蔗綿蚜(Ceratovacuna lanigera)、沬蟬科(Cercopidae)、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)、橘軟蠟蚧(Coccus pseudomagnoliarum)、黃綠介殼蟲(Coccus viridis))、黑茶藨隱瘤額蚜(Cryptomyzus ribis)、黃木蝨屬(Cryptoneossa spp.)、木蝨屬(Ctenarytaina spp.)、葉蟬屬(Dalbulus spp.)、Dialeurodes chittendeni、柑桔裸粉蝨(Dialeurodes citri)、柑橘木蝨(Diaphorina citri)、白背盾蚧屬(Diaspis spp.)、麥蚜屬(Diuraphis spp.)、棉蚜屬(Doralis spp.)、草履介殼蟲屬(Drosicha spp.)、圓尾蚜屬(Dysaphis spp.)(例如銹條蚜(Dysaphis apiifolia)、玫瑰蘋果蚜(Dysaphis plantaginea)、百合西圓尾蚜(Dysaphis tulipae)、嫡粉介殼蟲屬(Dysmicoccus spp.)、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)、索拉納小綠葉蝶(Empoasca solana)、Empoasca stevensi、蘋果棉蚜屬(Eriosoma spp.)(例如美洲榆綿蚜(Eriosoma americanum)、蘋果綿蚜(Eriosomalanigerum)、梨根綿蚜(Eriosoma pyricola)、斑葉蟬屬(Erythroneura spp.)、Eucalyptolyma屬、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))、片角葉蟬屬(Idiocerus spp.)、扁喙葉蟬屬(Idioscopus spp.)、斑飛蝨(Laodelphax striatellus)、蠟蚧屬(Lecanium spp.),(例如歐洲水果介殼蟲(Lecanium corni(=扁平球堅介殼蟲(Parthenolecanium corni)))、頓盾階屬(Lepidosaphes spp.)(例如榆蠣盾蚧(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)、Monelliopsis pecanis、瘤蚜屬(Myzus spp.)(例如冬蔥瘤額蚜(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)、黑尾葉蟬屬(Nephotettix spp.)(例如黑尾葉蟬(Nephotettix cincticeps)、黑條黑尾葉蟬(Nephotettix nigropictus)、Nettigoniclla spectra)、褐飛蝨(Nilaparvata lugens)、Oncometopia屬、狌蚧(Orthezia praelonga)、中華稻蝗(Oxya chinensis)、芽瘦木蝨屬(Pachypsylla spp.)、粉蝨(Parabemisia myricae)、木蝨屬(Paratrioza spp.)(例如番茄蝨(Paratrioza cockerelli))、黑星蚧屬(Parlatoria spp.)、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)、扁角飛蝨屬(Perkinsiella spp.)、綿粉介殼蟲屬(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)、Prosopidopsylla flava、厚綠原綿介殼蟲(Protopulvinaria pyriformis)、桑介殼蟲(Pseudaulacaspis pentagona))、禾草粉蚧屬(Pseudococcus spp.)(例如柑桔栖粉介殼蟲(Pseudococcus calceolariae)、康氏粉介殼蟲(Pseudococcus comstocki)、長尾粉介殼蟲(Pseudococcus longispinus)、海粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni))、Psyllopsis屬、木蝨屬(Psylla spp.)(例如黃楊木蝨(Psylla buxi)、蘋木蝨(Psylla mali)、梨木蝨(Psylla pyri))、金小蜂屬(Pteromalus spp.)、棉蚧屬(Pulvinaria spp.)、短足蠟蟬屬(Pyrilla spp.)、圓蚧屬(Quadraspidiotus spp.)(例如胡桃圓盾蚧(Quadraspidiotus juglansregiae)、歐洲果圓蚧(Quadraspidiotus ostreaeformis)、梨齒盾介殼蟲(Quadraspidiotus perniciosus)、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(Rhopalosiphum oxyacanthae)、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(Saissetia neglecta)、工脊硬介殼蟲(Saissetia oleae)、葡萄帶葉蟬(Scaphoideus titanus)、綠蚜(Schizaphis graminum)、刺圓盾介殼蟲(Selenaspidus articulatus)、牛鞭草蚜(Sipha flava)、麥長管蚜(Sitobion avenae)、白背飛蝨屬(Sogata spp.)、背飛蝨(Sogatella furcifera)、飛蝨屬(Sogatodes spp.)、沫蟬(Stictocephala festina)、梣粉蝨(Siphoninus phillyreae)、Tenalaphara malayensis、Tetragonocephela屬、胡桃黑蚜(Tinocallis caryaefoliae)、廣胸沫蜂屬(Tomaspis spp.)、聲蟲蚜屬(Toxoptera spp.),例如小桔蚜(Toxoptera aurantii)、大桔蚜(Toxoptera citricidus)、溫室粉蝨(Trialeurodes vaporariorum)、木蝨屬(Trioza spp.)(例如柿木蝨(Trioza diospyri))、小葉蟬屬(Typhlocyba spp.)、尖盾蚧屬(Unaspis spp.)、葡萄根瘤蚜(Viteus vitifolii)、斑葉蜂屬(Zygina spp.);來自異翅亞目(Heteroptera)之亞目,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)、異背長蝽屬(Cavelerius spp.)、臭蟲屬(Cimex spp.)(例如阿氏臭蟲(Cimex adjunctus)、熱帶臭蟲(Cimex hemipterus)、溫帶臭蟲(Cimex lectularius)、蝠臭蟲(Cimex pilosellus))、盲蝽屬(Collaria spp.)、綠盲蝽(Creontiades dilutus)、胡椒緣蝽(Dasynus piperis)、Dichelops furcatus、厚氏長棒網蜂(Diconocoris hewetti)、棉紅蝽屬(Dysdercus spp.)、美洲蝽屬(Euschistus spp.)(例如大豆褐蝽(Euschistus heros)、褐臭美洲蝽(Euschistus servus)、三色美洲蝽(Euschistus tristigmus)、單點美洲蝽(Euschistus variolarius))、菜蝽屬(Eurydema spp.)、扁盾蝽屬(Eurygaster spp.)、茶翅蝽(Halyomorpha halys)、錘盲蝽屬(Heliopeltis spp.)、具凹巨股長蝽(Horcias nobilellus)、稻緣蝽屬(Leptocorisa spp.)、異稻緣蝽(Leptocorisa varicornis)、西部喙緣蝽(Leptoglossus occidentalis)、葉喙緣蝽(Leptoglossus phyllopus)、麗盲蝽屬(Lygocoris spp.)(例如原麗盲蝽(Lygocoris pabulinus))、草盲蝽屬(Lygus spp.)(例如豆莢灰盲蝽(Lygus elisus)、雄性金星草盲椿(Lygus hesperus)、牧草盲蝽(Lygus lineolaris))、蔴漂長蝽(Macropes excavatus)、篩豆龜蝽(Megacopta cribraria)、盲椿象科(Miridae)、金光綠盲蝽(Monalonion atratum)、綠蝽屬(Nezara spp.)(例如稻綠蝽(Nezara viridula))、小長蝽屬(Nysius spp.)、稻蝽屬(Oebalus spp.)、蝽科(Pentomidae)、方背皮蝽(Piesma quadrata)、壁蝽屬(Piezodorus spp.)(例如蓋德擬壁蝽(Piezodorus guildinii))、雜盲蝽屬(Psallus spp.)、鱷梨網蝽(Pseudacysta persea)、紅獵蝽屬(Rhodnius spp.)、可可斑褐盲蝽(Sahlbergella singularis)、栗花椿象(Scaptocoris castanea)、黑蝽屬(Scotinophora spp.)、梨冠網蝽(Stephanitis nashi)、臭蟲屬(Tibraca spp.)、錐鼻蟲屬(Triatoma spp.);來自膜翅目(Hymenoptera)之目,例如頂切葉蟻屬(Acromyrmex spp.)、殘青葉蜂屬(Athalia spp.)(例如短斑殘青葉蜂(Athalia rosae))、切葉蟻屬(Atta spp.)、巨山蟻屬(Camponotus spp.)、長黃胡蜂屬(Dolichovespula spp.)、松葉蜂屬(Diprion spp.)(例如類歐松葉蜂(Diprion similis))、長角葉蜂屬(Hoplocampa spp.)(例如庫氏長角葉蜂(Hoplocampa cookei)、長角葉蜂蘋果長角葉蜂(Hoplocampa testudinea))、毛山蟻屬(Lasius spp.)、阿根廷螞蟻(Linepithema humile)(阿根廷虹臭蟻(Iridiomyrmex humile))、小黃家蟻(Monomorium pharaonis)、黃山蟻屬(Paratrechina spp.)、黃胡蜂屬(Paravespula spp.)、箭蟻屬(Plagiolepis spp.)、樹蜂屬(Sirex spp.)(例如雲杉樹蜂(Sirex noctilio))、入侵紅火蟻(Solenopsis invicta)、酸臭蟻屬(Tapinoma spp.)、白跗節狡臭蟻(Technomyrmex albipes)、大樹蜂屬(Urocerus spp.)、胡蜂屬(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)之目,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.)、土白蟻屬(Odontotermes spp.)、洞白蟻屬(Porotermes spp.)、散白蟻屬(Reticulitermes spp.),例如黃肢散白蟻(Reticulitermes flavipes)、西方散白蟻(Reticulitermes Hesperus));來自鱗翅目(Lepidoptera)之目,例如小蠟蛾(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)、小地老虎(Agrotis ipsilon))、波紋夜蛾屬(Alabama spp.)(例如棉葉波紋夜蛾(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)、黄螟屬(Argyroploce spp.)、丫紋夜蛾屬(Autographa spp.)、甘藍夜蛾(Barathra brassicae)、蘋髓尖蛾(Blastodacna atra)、秈弄蝶(Borbo cinnara)、棉潛蛾(Bucculatrix thurberiella)、松尺蠖(Bupalus piniarius)、蛀褐夜蛾屬(Busseola spp.)、捲葉蛾屬(Cacoecia spp.)、茶細蛾(Caloptilia theivora)、菸捲蛾(Capua reticulana)、蘋果蠹蛾(Carpocapsa pomonella)、桃小食心蟲(Carposina niponensis)、冬尺蛾(Cheimatobia brumata)、螟屬(Chilo spp.)(例如七星稻螟(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)、縱捲葉野螟屬(Cnaphalocerus spp.)、瘤野螟(Cnaphalocrocis medinalis)、雲捲蛾屬(Cnephasia spp.)、細蛾屬(Conopomorpha spp.)、球頸象屬(Conotrachelus spp.)、庫塔斯屬(Copitarsia spp.)、小捲蛾屬(Cydia spp.)(例如豌豆小捲蛾(Cydia nigricana))、蘋果蠹蛾(Cydia pomonella))、諾土德達拉卡(Dalaca noctuides)、絹野螟屬(Diaphania spp.)、棉鈴蟲屬(Diparopsis spp.)、小蔗螟(Diatraea saccharalis)、梢斑螟屬(Dioryctria spp.)(例如美洲松梢斑螟(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)、甘薯桿螟(Eldana saccharina)、粉斑螟屬(Ephestia spp.)(例如菸草粉斑螟(Ephestia elutella)、地中海粉斑螟(Ephestia kuehniella))、葉小捲蛾屬(Epinotia spp.)、蘋果褐捲蛾(Epiphyas postvittana)、松尺蛾屬(Erannis spp.)、灰紋捲蛾(Erschoviella musculana)、莢斑螟屬(Etiella spp.)、豔葉夜蛾屬(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))、實夜蛾屬(Heliothis spp.)(例如煙芽夜蛾(Heliothis virescens))、褐織蛾(Hofmannophila pseudospretella)、斑螟屬(Homoeosoma spp.)、長捲蛾屬(Homona spp.)、櫻桃巢蛾(Hyponomeuta padella)、柿蔕蟲蛾(Kakivoria flavofasciata)、亮灰蝶屬(Lampides spp.)、夜蛾屬(Laphygma spp.)、梨小蠹螟(Laspeyresia molesta)、茄黃斑螟(Leucinodes orbonalis)、銀潛蛾屬(例如咖啡銀潛蛾)、潛葉細蛾屬(Lithocolletis spp.)(例如蘋果斑幕潛葉細蛾(Lithocolletis blancardella))、綠果冬夜蛾(Lithophane antennata)、花翅小蛾屬(Lobesia spp.)(例如葡萄花翅小蛾(Lobesia botrana))、豆白隆切根蟲(Loxagrotis albicosta)、毒蛾屬(Lymantria spp.)(例如舞毒蛾(Lymantria dispar))、潛蛾屬(Lyonetia spp.)(例如桃潛蛾(Lyonetia clerkella))、天幕毛蟲(Malacosoma neustria)、豆莢野螟(Maruca testulalis)、甘藍夜蛾(Mamestra brassicae)、稻暮眼蝶(Melanitis leda)、毛脛夜蛾屬(Mocis spp.)、Monopis obviella、黏夜蛾(Mythimna separata)、橡長角蛾(Nemapogon cloacellus)、水螟屬(Nymphula spp.)、Oiketicus屬、蠹野螟屬(Omphisa spp.)、尺蛾屬(Operophtera spp.)、巫夜蛾屬(Oria spp.)、瘤叢螟屬(Orthaga spp.)、玉米螟屬(Ostrinia spp.)(例如歐洲玉米螟(Ostrinia nubilalis))、松夜蛾(Panolis flammea)、稻弄蝶屬(Parnara spp.)、紅鈴蟲屬(Pectinophora spp.)(例如棉紅鈴蟲(Pectinophora gossypiella))、潛跳甲屬(Perileucoptera spp.)、茄麥蛾屬(Phthorimaea spp.)(例如馬鈴薯塊莖蛾(Phthorimaea operculella))、柑橘潛葉蛾(Phyllocnistis citrella)、小潛細蛾屬(Phyllonorycter spp.)(例如幕斑小潛細蛾(Phyllonorycter blancardella)、山楂小潛細蛾(Phyllonorycter crataegella))、白粉蝶屬(Pieris spp.)(例如紋白蝶(Pieris rapae))、荷蘭石竹小捲蛾(Platynota stultana)、印度穀螟(Plodia interpunctella)、金翅夜蛾屬(Plusia spp.)、小菜蛾(Plutella xylostella)(=小菜蛾(Plutella maculipennis))、Podesia屬(例如Podesia syringae)、小白巢蛾屬(Prays spp.)、Prodenia屬、菸草天蛾(Protoparce spp.)、黏蟲屬(Pseudaletia spp.)(例如一星黏蟲(Pseudaletia unipuncta)、大豆尺夜蛾(Pseudoplusia includens)、歐洲玉蜀黍螟(Pyrausta nubilalis)、薄荷灰夜蛾(Rachiplusia nu)、禾螟屬(Schoenobius spp.)(例如三化螟(Schoenobius bipunctifer))、白禾螟屬(Scirpophaga spp.)(例如稻白禾螟(Scirpophaga innotata))、黃地老虎(Scotia segetum)、蛀莖夜蛾屬(Sesamia spp.)(例如稻蛀莖夜蛾(Sesamia inferens))、長須捲蛾屬(Sparganothis spp.)、灰翅夜蛾屬(Spodoptera spp.)(例如厄地那灰翅夜蛾(Spodoptera eradiana)、甜菜葉蛾(Spodoptera exigua)、草地夜蛾(Spodoptera frugiperda))、條狀黏蟲(Spodoptera praefica)、舉肢蛾屬(Stathmopoda spp.)、黃鵪菜屬(Stenoma spp.)、花生須峭麥蛾(Stomopteryx subsecivella)、透翅蛾屬(Synanthedon spp.)、安第斯馬鈴薯塊莖蛾(Tecia solanivora)、異舟蛾屬(Thaumetopoea spp.)、幹煞 夜蛾(Thermesia gemmatalis)、木塞衣蛾(Tinea cloacella)、衣蛾(Tinea pellionella)、袋衣蛾(Tineola bisselliella)、捲葉蛾屬(Tortrix spp.)、毛氈衣蛾屬(Trichophaga tapetzella)、粉夜蛾屬(Trichoplusia spp.)(例如粉紋夜蛾(Trichoplusia ni))、三化螟(Tryporyza incertulas)、番茄斑潛蠅(Tuta absoluta)、灰蝶屬(Virachola spp.);來自直翅目(Orthoptera)或跳躍亞目(Saltatoria)之目,例如家蟋蟀(Acheta domesticus)、Dichroplus屬、螻蛄屬(Gryllotalpa spp.)(例如歐洲螻蛄(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)、沙漠蝗蟲(Schistocerca gregaria);來自毛蝨目(Phthiraptera)之目,例如畜蝨屬(Damalinia spp.)、血蝨屬(Haematopinus spp.)、長齶蝨屬(Linognathus spp.)、蝨屬(Pediculus spp.)、葡萄根瘤蚜(Phylloxera vastatrix)、陰蝨(Phthirus pubis)、毛蝨屬(Trichodectes spp.);來自囓蟲目(Psocoptera)之目,例如鱗齧蟲屬(Lepinotus spp.)、蝨囓屬(Liposcelis spp.);來自隱翅目(Siphonaptera)之目,例如角葉蚤屬(Ceratophyllus spp.)、櫛頭蚤屬(Ctenocephalides spp.)(例如犬櫛頭蚤(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)之目,例如玉米黃呆薊馬(Anaphothrips obscurus)、稻薊馬(Baliothrips biformis)、中斑圍孔薊馬(Chaetanaphothrips leeuweni)、鮮食葡萄鐮薊馬(Drepanothrips reuteri)、黃化恩薊馬(Enneothrips flavens)、花薊馬屬(Frankliniella spp.)(例如菸褐花薊馬(Frankliniella fusca)、西花薊馬(Frankliniella occidentalis)、梳缺花薊馬(Frankliniella schultzei)、美東花薊馬(Frankliniella tritici)、越橘花薊馬(Frankliniella vaccinii)、威廉期花薊馬(Frankliniella williamsi))、簡管薊馬屬(Haplothrips spp.)、陽薊馬屬(Heliothrips spp.)、溫室條籬薊馬(Hercinothrips femoralis)、卡薊馬屬(Kakothrips spp.)、腹鉤薊馬 (Rhipiphorothrips cruentatus)、硬薊馬屬(Scirtothrips spp.)、豆塔薊馬(Taeniothrips cardamomi)、薊馬屬(Thrips spp.)(例如南黃薊馬(Thrips palmi)、蔥薊馬(Thrips tabaci));來自衣魚亞目(Zygentoma)(=纓尾目(Thysanura))之目,例如櫛衣魚屬(Ctenolepisma spp.)、普通衣魚(Lepisma saccharina)、盜火蟲(Lepismodes inquilinus)、斑衣魚(Thermobia domestica);來自結閥綱(Symphyla)之綱,例如麼蚰屬(Scutigerella spp.)(例如白松蟲(Scutigerella immaculata);來自軟體動物門(Mollusca)之門,例如來自雙殼綱(Bivalvia)(例如飾貝屬(Dreissena spp.);以及來自腹足綱(Gastropoda)之綱,例如阿勇蛞蝓屬(Arion spp.)(例如愛特盧夫斯阿勇蛞蝓(Arion ater rufus))、雙臍螺屬(Biomphalaria spp.)、泡螺屬(Bulinus spp.)、野蛞蝓屬(Deroceras spp.)(例如光滑野蛞蝓(Deroceras laeve))、土蝸屬(Galba spp.)、椎實螺屬(Lymnaea spp.)、釘螺屬(Oncomelania spp.)、福壽螺屬(Pomacea spp.)、琥珀螺屬(Succinea spp.);來自圓形動物門(Nematoda)之門的植物害蟲,即植物寄生線蟲,特別為野外墊刃線蟲屬(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.)(例如細小刺線蟲(Belonolaimus gracilis)、雜草刺線蟲(Belonolaimus longicaudatus)、諾頓剌線蟲(Belonolaimus nortoni))、傘滑刃線蟲屬(Bursaphelenchus spp.)(例如椰樹傘滑刃線蟲(Bursaphelenchus cocophilus)、荒漠傘滑刃線蟲(Bursaphelenchus eremus)、松材傘滑刃線蟲(Bursaphelenchus xylophilus))、壞死線蟲屬(Cacopaurus spp.)(例如癌疫壞死線蟲(Cacopaurus pestis))、小環線蟲屬(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)、如思木小環線蟲(Criconemella rusium)、薄葉小環線蟲(Criconemella xenoplax)(=異盤中環線蟲(Mesocriconema xenoplax)))、輪線蟲屬(Criconemoides spp.)(例如非尼艾輪線蟲(Criconemoides ferniae)、蝸諾昔輪線蟲(Criconemoides onoense)、蝸那土輪線蟲(Criconemoides ornatum))、莖線蟲屬(Ditylenchus spp.)(例如鱗球莖莖線蟲(Ditylenchus dipsaci))、錐線蟲屬(Dolichodorus spp.)、球胞囊線蟲屬(Globodera spp.)(例如馬鈴薯球胞囊線蟲(Globodera pallida)、馬鈴薯金線蟲(Globodera rostochiensis))、螺旋線蟲屬(Helicotylenchus spp.)(例如雙宮螺旋線蟲(Helicotylenchus dihystera))、半輪線蟲屬(Hemicriconemoides spp.)、鞘線蟲屬(Hemicycliophora spp.)、異皮線蟲屬(Heterodera spp.)(例如燕麥異皮線蟲(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.)、長針線蟲屬(Longidorus spp.)(例如非洲長針線蟲(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.)、擬滑刃屬(Paraphelenchus spp.)、擬毛刺線蟲屬(Paratrichodorus spp.)(例如微小擬毛刺線蟲(Paratrichodorus minor))、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.)、平滑墊刃線蟲屬(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)、香蕉穿孔線蟲(Radopholus similis))、腎型線蟲屬(Rotylenchulus spp.)、盤旋線蟲屬(Rotylenchus spp.)、盾線蟲屬(Scutellonema spp.)、亞粒線蟲屬(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 primitives))、矮化線蟲屬(Tylenchorhynchus spp.)(例如飾環矮化線蟲(Tyenchorhynchus annulatus))、穿刺線蟲屬(Tylenchulus spp.)(例如半穿刺線蟲(Tylenchulus semipenetrans))、劍線蟲屬(Xiphinema spp.)(例如標記劍線蟲(Xiphinema index))。
視情況而定,式(I)化合物於某些濃度或施用率下亦可用作為除草 劑、安全劑、生長調節劑或改良植物性質之劑、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(mycoplasma-like organism))及RLO(類立克次體有機體(rickettsia-like organism))之劑。視情況而定,彼等亦可用作為合成其他活性成分之中間物或前驅物。
本發明進一步關於配製物及由其製備之作為除害劑的使用形式(例如澆灌、滴注及噴灑液),其包含至少一種式(I)化合物。視情況地,使用形式包含其他除害劑及/或改良作用之佐劑,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/或滯留促進劑(例如磺醯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)。
習知的配製物為(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);此等及其他可能的配製物類型例如係由Crop Life International說明及說明於由FAO/WHO除害劑規格聯合會議(FAO/WHO Joint Meeting on Pesticide Specifications,2004,ISBN:9251048576)所編製之Pesticide Specifications,Manual on development and use of FAO and WHO specifications for pesticides,FAO Plant Production and Protection Papers-173中。除了一或多種式(I)化合物以外,配製物可視情況地包含其他活性農化成分。
較佳者為包含助劑(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/或其他助劑,例如佐劑)的配製物或使用形式。在此情況下佐劑為增進配製物的生物作用之組分,該組分本身不具有任何生物作用。佐劑之實例為促進滯留、擴散、附著於葉表面或滲透之劑。
此等配製物係以已知的方式製造,例如藉由將式(I)化合物與助劑(例如增量劑、溶劑及/或固體載劑及/或其他助劑,例如界面活性劑)混 合。配製物係在適當設備中或者在施用前或期間製造。
所使用的助劑可為適合於將特定性質(諸如某些物理、技術及/或生物性質)賦予式(I)化合物之配製物或由此等配製物所製備之使用形式(例如,備用除害劑諸如噴灑液或拌種產物)的物質。
適當增量劑為(例如)水、極性和非極性有機化學液體,例如選自下列類別: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、簡單及經取代的胺、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亞碸),以及水。
原則上,可能使用所有適當溶劑。適當溶劑之實例為芳族烴(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、石蠟、石油分餾物、礦物油和植物油)、醇(諸如甲醇、乙醇、異丙醇、丁醇或二醇)及其醚和酯、酮(諸如丙酮、甲基乙酮、甲基異丁酮或環己酮)、強極性溶劑(諸如二甲亞碸),以及水。
原則上,可能使用所有適當載劑。適當載劑更特別地包括下列:例如銨鹽、天然細磨礦物(諸如高嶺土、氧化鋁、滑石、白堊、石英、鎂鋁海泡石、蒙脫土或矽藻土)及合成細磨礦物(諸如高分散性矽石、氧化鋁和天然或合成矽酸鹽)、樹脂、蠟及/或固體肥料。同樣地可能使用該等載劑之混合物。用於粒劑之有用載劑包括: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)及無機和有機粉末之合成顆粒,及亦為有機材料(諸如鋸屑、紙、椰子殼、玉米穗軸和菸草稈)之顆粒。
亦可使用液化氣體增量劑或溶劑。尤其適合的增量劑或載劑為彼 等在標準溫度下及在大氣壓力下為氣體的增量劑或載劑,例如氣霧推進劑,諸如鹵化烴,以及丁烷、丙烷、氮和二氧化碳。
具有離子或非離子性質之乳化劑及/或泡沫形成劑、分散劑或潤濕劑,或此等界面活性物質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酚(較佳為烷基酚或芳基酚)之聚縮物、磺酸基琥珀酸酯之鹽、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,例如烷基芳基聚乙二醇醚、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯、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用係發生在水中時,則界面活性劑的存在是有利的。
可存在於配製物及由其所衍生之使用形式中的其他助劑包括染料(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)。
可存在的另外組分可為穩定劑(諸如冷穩定劑)、防腐劑、抗氧化劑、光穩定劑或其他改良化學及/或物理穩定性之劑。亦可存在泡沫產生劑或消泡劑。
此外,配製物及由其所衍生之使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)、或天然磷脂(諸如腦磷脂和卵磷脂)及合成磷脂作為另外的助劑。其他助劑可為礦物油與植物油。
若適當時,其他助劑可能存在於配製物及由其所衍生之使用形式中。該等添加劑的實例包括香料、保護性膠體、黏合劑、黏著劑、增稠劑、觸變劑、滲透劑、滯留促進劑、穩定劑、螯合劑、錯合劑、保濕劑、擴散劑。通常,可將式(I)化合物與習用於調配目的之任何固體或液體添加劑組合。
有用的滯留促進劑包括所有彼等減少動態表面張力之物質,例如磺酸基琥珀酸二辛酯,或增加黏彈性之物質,例如羥丙基膠豆聚合物。
有用的滲透劑在本情況下為所有彼等通常用於改良活性農化成分滲透至植物中之物質。滲透劑在此情況下係以彼等自(通常為水性)施用液體及/或自噴灑塗層滲透至植物的角質層且因此增加活性成分在角質層中的移動性之能力來定義。文獻(Baur等人之1997,Pesticide Science 51,131-152)中所述之方法可用於測定此性質。實例包括醇烷氧化物(例如,椰子脂肪乙氧化物(10)或異十三基乙氧化物(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,牛脂胺乙氧化物(15))、或銨及/或鏻鹽(例如,硫酸銨或磷酸氫二銨)。
配製物較佳地包含以配製物的重量為基準計介於0.00000001重量%和98重量%之間的式(I)化合物,更佳地介於0.01重量%和95重量%之間的式(I)化合物,最佳地介於0.5重量%和90重量%之間的式(I)化合物。
在由配製物製備之使用形式(特別是除害劑)中的式(I)化合物之含量可在寬廣的範圍內改變。使用形式中的式(I)化合物之濃度通常可為以使用形式的重量為基準計介於0.00000001重量%和95重量%之間的式(I)化合物,較佳為介於0.00001重量%和1重量%之間。施用係以適合於使用形式的習知方式完成。
混合物
式(I)化合物亦可以與一種或多種適當殺真菌劑、殺細菌劑、殺蟎劑、殺軟體動物劑、殺線蟲劑、殺蟲劑、微生物劑、有益生物、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使用,以因此例如擴增作用範圍、延長作用期間、增加作用率、防止排斥或防止抗性進化。此外,此種類的活性成分組合可改良植物生長及/或對非生物因子(例如,高或低溫、乾旱或含水量升高或土壤鹽度)之耐受性。亦可能改良開花和結果性能、最佳化發芽能力和根發育、促進收成和改良產率、影響成熟、改良收成產物之品質及/或營養價值、延長貯藏壽命及/或改良收成產物之加工性。
此外,式(I)化合物可以與其他的活性成分或化學傳訊素(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)之混合物 存在。同樣地,式(I)化合物可使用於改良植物性質,例如收成材料的生長、產率及品質。
在根據本發明一特殊實施態樣中,式(I)化合物係以與其他化合物(較佳為彼等如下所述者)之混合物存在於配製物或由此等配製物所製備之使用形式中。
若下述化合物中之一者可以各種互變異構物形式出現時,則亦包括此等形式,即使在各情形下未明確述及。所提及的所有混合組分視情況而定亦可與適當鹼或酸形成鹽,若彼等根據其官能基能夠如此的話。
在本文中以彼等的俗名指定之活性成分為已知且描述於(例如)“除害劑手冊”(The Pesticide Manual,16th ed.,British Crop Protection Council 2012)中或可在網際網路上搜尋(例如http://www.alanwood.net/pesticides)。分類係根據在本專利申請案申請時適用的作用分類方案之IRAC模式(IRAC Mode of Action Classification Scheme)。
(1)乙醯膽鹼酯酶(AChE)抑制劑,例如胺基甲酸酯類,例如棉鈴威(alanycarb)、得滅克(aldicarb)、免敵克(bendiocarb)、免扶克(benfuracarb)、佈嘉信(butocarboxim)、丁酮碸威(butoxycarboxim)、加保利(carbaryl)、加保扶(carbofuran)、丁基加保扶(carbosulfan)、愛芬克(ethiofencarb)、丁基滅必蝨(fenobucarb)、覆滅竝(formetanate)、扶線威(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)、硫伐隆(thiofanox)、唑蚜威(triazamate)、混殺威(trimethacarb)、XMC及滅爾蝨(xylylcarb);或有機磷酸鹽類,例如歐殺松(acephate)、亞滅松(azamethiphos)、谷速松(azinphos)-乙基、谷速松-甲基、硫線磷(cadusafos)、氯氧磷(chlorethoxyfos)、克芬松(chlorfenvinphos)、氯甲硫磷(chlormephos)、陶斯松(chlorpyrifos)-甲基、牛壁逃(coumaphos)、氰乃松(cyanophos)、滅賜松(demeton-S-methyl)、大利松(diazinon)、二氯松 (dichlorvos)/DDVP、雙特松(dicrotophos)、大滅松(dimethoate)、甲基毒蟲畏(dimethylvinphos)、二硫松(disulfoton)、EPN、愛殺松(ethion)、普伏松(ethoprophos)、氨磺磷(famphur)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬殺松(fenthion)、福賽絕(fosthiazate)、飛達松(heptenophos)、依米賽松(imicyafos)、亞芬松(isofenphos)、水楊酸O-(甲氧胺基硫磷醯基)酯異丙酯、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)、乃力松(naled)、歐滅松(omethoate)、滅多松(oxydemeton-methyl)、巴拉松(parathion)-甲基、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-methyl)、佈飛松(profenofos)、撲達松(propetamphos)、普硫松(prothiofos)、白克松(pyraclofos)、必芬松(pyridaphenthion)、拜裕松(quinalphos)、硫特普(sulfotep)、丁嘧硫磷(tebupirimfos)、亞培松(temephos)、托福松(terbufos)、樂本松(tetrachlorvinphos)、硫滅松(thiometon)、三落松(triazophos)、三氯松(triclorfon)及繁米松(vamidothion)。
(2)GABA-閘控之氯離子通道阻斷劑,例如環二烯有機氯類,例如克氯丹(chlordane)及安殺番(endosulfan)或苯基吡唑類(飛普洛類(fiproles))(例如乙蟲清(ethiprole)及芬普尼(fipronil)。
(3)鈉通道調節劑,例如擬除蟲菊酯類(pyrethroids)(例如阿納寧(acrinathrin)、亞列寧(allethrin)、d-順-反亞列寧、d-反亞列寧、畢芬寧(bifenthrin)、百亞列寧(bioallethrin)、百亞列寧-s-環戊烯基異構物、百列滅寧(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、亞滅寧(cypermethrin)、α-亞滅寧、β-亞滅寧、θ-亞滅寧、ξ-亞滅寧、賽芬寧(cyphenothrin)[(1R)-反式異構物]、第滅寧(deltamethrin)、益避寧(empenthrin)[(EZ)-(1R)異構物]、益化利(esfenvalerate)、依芬寧(etofenprox)、芬普寧(fenpropathrin)、芬化利(fenvalerate)、護賽寧(flucythrinate)、福滅寧(flumethrin)、福化利(τ-fluvalinate)、合芬寧 (halfenprox)、依普寧(imiprothrin)、剋特寧(kadethrin)、莫弗洛寧(momfluorothrin)、百滅寧(permethrin)、酚丁滅蝨(phenothrin)[(1R)-反-異構物]、普亞列寧(prallethrin)、除蟲菊素(pyrethrins)(除蟲菊精(pyrethrum))、列滅寧(resmethrin)、氟矽菊酯(silafluofen)、七氟菊酯(tefluthrin)、治滅寧(tetramethrin)、治滅寧[(1R)異構物]、泰滅寧(tralomethrin)和拜富寧(transfluthrin)或DDT或甲氧滴滴涕(methoxychlor)。
(4)菸鹼乙醯膽鹼受體(nAChR)競爭調節劑,例如新菸鹼類,例如亞滅培(acetamiprid)、可尼丁(clothianidin)、達特南(dinotefuran)、益達胺(imidacloprid)、烯啶蟲胺(nitenpyram)、噻蟲啉(thiacloprid)和賽速安(thiamethoxam)或尼古丁(nicotine)或氟啶蟲胺腈(sulfoxatlor)或氟吡呋喃酮(flupyradifurone)。
(5)菸鹼乙醯膽鹼受體(nAChR)別位調節劑,例如賜諾斯類(spinosyns)(例如賜諾特(spinetoram)和賜諾殺(spinosad)。
(6)麩胺酸閘控之氯離子通道(GluCl)別位調節劑,例如阿維菌素(avermectins)/米貝黴素(milbemycins)(例如阿巴汀(abamectin)、因滅汀(emamectin benzoate)、雷皮菌素(lepimectin)和密滅汀(milbemectin)。
(7)保幼激素模擬物,例如保幼激素類似物,例如烯蟲乙酯(hydroprene)、烯蟲炔酯(kinoprene)和美賜平(methoprene)或芬諾克(fenoxycarb)或百利普芬(pyriproxyfen)。
(8)雜項非特異性(多位置)抑制劑,例如鹵烷類,例如溴甲烷及其他鹵烷類;或氯化苦(chloropicrin)或硫醯氟(sulphuryl fluoride)或硼砂(borax)或吐酒石或異氰酸甲酯產生劑,例如邁隆(diazomet)和斯美地(metam)。
(9)弦音器調節劑,如吡蚜酮(pymetrozine)或氟啶蟲醯胺(flonicamide)。
(10)蟎生長抑制劑,例如克芬蟎(clofentezine)、合賽多(hexythiazox)、氟蟎嗪(diflovidazin)或依殺蟎(etoxazole)。
(11)昆蟲腸膜之微生物干擾劑,例如蘇力菌以色列亞種(Bacillus thuringiensis subspecies israelensis)、球形芽孢桿菌(Bacillus sphaericus)、 蘇力菌鮎澤亞種(Bacillus thuringiensis subspecies aizawai)、蘇力菌庫斯克亞種(Bacillus thuringiensis subspecies kurstaki)、蘇力菌擬步行蟲亞種(Bacillus thuringiensis subspecies tenebrionis),及BT植物蛋白質:Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb和Cry34Ab1/35Ab1。
(12)粒腺體ATP合成酶之抑制劑,諸如ATP干擾劑,例如汰芬隆(diafenthiuron)或有機錫化合物,例如亞環錫(azocyclotin)、錫蟎丹(cyhexatin)及芬佈賜(fenbutatin oxide)或毆蟎多(propargite)或得脫蟎(tetradifon)。
(13)經由質子梯度干擾之氧化性磷酸化去偶合劑,例如克凡派(chlorfenapyr)、DNOC及氟蟲胺(sulfluramid)。
(14)菸鹼乙醯膽鹼受體通道阻斷劑,例如免速達(bensultap)、培丹(cartap)鹽酸鹽、硫賜安(thiocylam)及殺蟲雙(thiosultap-sodium)。
(15)第0型甲殼素生物合成之抑制劑,例如雙三氟蟲脲(bistrifluron)、克福隆(chlortluazuron)、二福隆(diflubenzuron)、氟蟎脲(flucycloxuron)、氟芬隆(flufenoxuron)、六伏隆(hexaflumuron)、祿芬隆(lufenuron)、諾伐隆(novaluron)、諾伏隆(noviflumuron)、得福隆(teflubenzuron)及三伏隆(triflumuron)。
(16)第1型甲殼素生物合成抑制劑,例如布芬淨(buprofezin)。
(17)脫皮干擾劑(特別是用於雙翅目(Diptera)的情況下)(例如賽滅淨(cyromazine)。
(18)蛻皮激素受體促效劑,例如可芬諾(chromafenozide)、氯蟲醯肼(halofenozide)、滅芬諾(methoxyfenozide)及得芬諾(tebufenozide)。
(19)章魚胺能受體促效劑,例如三亞蟎(amitraz)。
(20)粒腺體複合物III電子傳遞抑制劑,例如海滅隆(hydramethylnone)或亞醌蟎(acequinocyl)或嘧蟎酯(fluacrypyrim)。
(21)粒腺體複合物I電子傳遞抑制劑,例如METI殺蟎劑,例如芬殺蟎(fenazaquin)、芬普蟎(fenpyroximate)、畢汰芬(pyrimidifen)、畢達本(pyridaben)、得芬瑞(tebufenpyrad)及脫芬瑞(tolfenpyrad)或魚藤酮(rotenone)(Derris)。
(22)電壓依賴性鈉通道阻斷劑,例如因得克(indoxacarb)或美氟綜(metaflumizone)。
(23)乙醯基CoA羧酶之抑制劑,例如特窗酸和特密酸(tetramic acid)衍生物,例如賜派芬(spirodiclofen)、螺甲蟎酯(spiromesifen)及螺蟲乙酯(spirotetramat)。
(24)粒腺體複合物IV電子傳遞抑制劑,例如膦類,例如磷化鋁、磷化鈣、膦及磷化鋅,或氰化物,例如氰化鈣、氰化鉀和氰化鈉。
(25)粒腺體複合物II電子傳遞抑制劑,例如β-酮腈衍生物,例如腈吡蟎酯(cyenopyrafen)及賽芬蟎(cyflumetofen),及羧醯替苯胺類,例如派福佈麥(pyflubumide)。
(28)藍尼定(Ryanodine)受體調節劑,例如二醯胺類,例如氯蟲醯胺(chlorantraniliprole)、氰蟲醯胺(cyantraniliprole)及氟蟲醯胺(flubendiamide),
其他活性化合物,例如艾飛撲平(afidopyropen)、阿佛拉那(afoxolaner)、印楝素(azadirachtin)、苯洛賽(benclothiaz)、西脫蟎(benzoximate)、聯苯肼酯(bifenazate)、布洛苯胺(broflanilide)、新殺蟎(bromopropylate)、蟎離丹(chinomethionat)、氯普亞列寧(chloroprallethrin)、冰晶石(cryolite)、環溴蟲醯胺(cyclaniliprole)、環氧蟲啶(cycloxaprid)、氯氟氰蟲醯胺(cyhalodiamide)、二氯滅嗪(dicloromezotiaz)、大克蟎(dicofol)、ε-甲氧苄氟菊酯(metofluthrin)、ε-莫弗洛寧(momfluthrin)、芬滅克(flometoquin)、氟紮吲哚巾(fluazaindolizine)、氟噻蟲碸(fluensulfone)、嘧蟲胺(flufenerim)、氟菌蟎酯(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)、右旋七氟甲醚菊酯(heptafluthrin)、氯噻啉(imidaclothiz)、依普同(iprodione)、κ-畢芬寧(bifenthrin)、κ-七氟菊酯(tefluthrin)、羅提蘭(lotilaner)、氯氟醚菊酯(meperfluthrin)、哌蟲啶(paichongding)、必達利(pyridalyl)、必伏隆(pyrifluquinazon)、嘧蟎胺(pyriminostrobin)、螺蟎雙酯(spirobudiclofen)、四氟醚菊酯(tetramethylfluthrin)、四尼利普洛(tetraniliprole)、四氯查尼 普洛(tetrachlorantraniliprole)、替阿札芬(tioxazafen)、硫氟肟醚(thiofluoximate)、三氟米比瑞(triflumezopyrim)和碘甲烷;另外以堅強桿菌(Bacillus firmus)為主之製劑(I-1582,BioNeem,Votivo)、以及下列化合物: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(從WO2006/043635得知)(CAS 885026-50-6)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(從WO2003/106457得知)(CAS 637360-23-7)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]異菸鹼醯胺(從WO2006/003494得知)(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(從WO 2010052161得知)(CAS 1225292-17-0)、碳酸3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-側氧-1,8-二氮雜螺[4.5]癸-3-烯-4-基酯乙基酯(從EP 2647626得知)(CAS-1440516-42-6)、4-(丁-2-炔-1-基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(從WO2004/099160得知)(CAS 792914-58-0)、PF1364(從JP2010/018586得知)(CAS 1204776-60-2)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]吡啶-2(1H)-亞基]-2,2,2-三氟乙醯胺(從WO2012/029672得知)(CAS 1363400-41-2)、(3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亞基]-1,1,1-三氟丙-2-酮(從WO2013/144213得知)(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-甲醯胺(從WO2010/051926得知)(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-甲醯胺(從CN103232431得知)(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-1-氧負離子基-3-硫呾基)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-1-氧負離子基-3-硫呾基)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-1-氧負離子基-3-硫呾基)苯甲醯胺(從WO 2013/050317 A1得知)(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(從WO 2013/162715 A2、WO 2013/162716 A2、US 2014/0213448 A1得知)(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(從CN 101337937 A得知)(CAS 1105672-77-2)、3-溴-N-[4-氯-2-甲基-6-[(甲胺基)硫酮基甲基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺、(Liudaibenjiaxuanan,從CN 103109816 A得知)(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-甲醯胺(從WO 2012/034403 A1得知)(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-甲醯胺(從WO 2011/085575 A1得知)(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(從CN 101337940 A得知)(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]肼甲醯胺(從CN 101715774 A得知)(CAS 1232543-85-9);環丙烷甲酸3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H-苯并咪唑-2-基)苯基酯(從CN 103524422 A得知)(CAS 1542271-46-4);(4aS)-7-氯-2,5-二氫-2-[[(甲氧羰基)[4-[(三氟甲基)硫基]苯基]胺基]羰基]茚并[1,2-e][1,3,4]二-4a(3H)-甲酸甲酯(從CN 102391261 A得知)(CAS 1370358-69-2);6-去氧基-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-哌喃甘露糖(從US 2014/0275503 A1得知)(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-反側)-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-同側)-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(從WO 2007040280 A1、WO 2007040282 A1得知)(CAS 934001-66-8)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)硫基]-丙醯胺(從WO 2015/058021 A1、WO 2015/058028 A1得知)(CAS 1477919-27-9)和N-[4-(胺基硫酮基甲基)-2-甲基-6-[(甲胺基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(從CN 103265527 A得知)(CAS 1452877-50-7)。
在本文中以彼等的俗名指定之活性成分為已知且描述於(例如)“除害劑手冊”(The Pesticide Manual,16th ed.,British Crop Protection Council 2012)中或可在網際網路上搜尋(例如http://www.alanwood.net/pesticides)。
類別(1)至(15)中所提及的所有混合組分視情況而定亦可與適當鹼或酸形成鹽,若彼等根據其官能基能夠如此的話。類別(1)至(15)中所提及的所有殺真菌混合組分視情況而定可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)環克座(cyproconazole)、(1.002)待克利(difenoconazole)、(1.003)依普座(epoxiconazole)、(1.004)環醯菌胺(fenhexamid)、(1.005)苯鏽啶(fenpropidin)、(1.006)芬普福(fenpropimorpH),(1.007)胺苯吡菌酮(fenpyrazamine)、(1.008)氟喹唑(fluquinconazole)、(1.009)護汰芬(flutriafole)、(1.010)依滅列(imazalil)、(1.011)依滅列硫酸鹽、(1.012)種菌唑(ipconazole)、(1.013)滅特座(metconazole)、(1.014)邁克尼(myclobutanil)、(1.015)巴克素(paclobutrazol)、(1.016)撲克拉(prochloraz)、((1.017)普克利(propiconazole)、(1.018)丙硫菌唑(prothioconazole)、(1.019)啶菌唑(pyrisoxazole)、(1.020)葚孢菌素(spiroxamine)、(1.021)得克利(tebuconazole)、(1.022)四克利(tetraconazole)、(1.023)三泰隆(triadimenol)、(1.024)三得芬(tridemorpH),(1.025)滅菌唑(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-1,3-二柬-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-1,3-二柬-2-基}甲基)-1H-1,2,4-三唑、(1.039)硫氰酸1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)氧元-2-基]甲基}-1H-1,2,4-三唑-5-基酯、(1.040)硫氰酸1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧元-2-基]甲基}-1H-1,2,4-三唑-5-基酯、(1.041)硫氰酸1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧元-2-基]甲基}-1H-1,2,4-三唑-5-基酯、(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)氧元-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)氧元-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)氧元-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-(烯丙基硫烷基)-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)氧元-2-基]甲基}-1H-1,2,4-三唑、(1.061)5-(烯丙基硫烷基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧元-2-基]甲基}-1H-1,2,4-三唑、(1.062)5-(烯丙基硫烷基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧元-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]硫烷基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.064)N'-(2,5-二甲基-4-{[3-(2,2,2-三氟乙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.065)N'-(2,5-二甲基-4-{[3-(2,2,3,3-四氟丙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.066)N'-(2,5-二甲基-4-{[3-(五氟乙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.067)N'-(2,5-二甲基-4-{3-[(1,1,2,2-四氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.068)N'-(2,5-二甲基-4-{3-[(2,2,2-三氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.069)N'-(2,5-二甲基-4-{3-[(2,2,3,3-四氟丙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.070)N'-(2,5-二甲基-4-{3-[(五氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.071)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.072)N'-(4-{[3-(二氟甲氧基)苯基]硫烷基}-2,5-二甲基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.073)N'-(4-{3-[(二氟甲基)硫烷基]苯氧基}-2,5-二甲基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.074)N'-[5-溴-6-(2,3-二氫-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基亞胺基甲醯胺、(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-甲基亞胺基甲醯胺、(1.078)N'-{5-溴-6-[(順--4-異丙基環己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.079)N'-{5-溴-6-[(反-4-異丙基環己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(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-甲基亞胺基甲醯胺、(1.081)美芬三康唑(mefentrifluconazole)、(1.082)伊芬三康唑(ipfentrifluconazole)。
2)於複合物I或II的呼吸鏈之抑制劑,例如(2.001)苯并烯氟菌唑(benzovindiflupyr)、(2.002)必殺芬(bixafen)、(2.003)白克列(boscalid)、(2.004)萎銹靈(carboxin)、(2.005)氟吡菌醯胺(fluopyram)、(2.006)福多寧(flutolanil)、(2.007)氟唑菌醯胺(fluxapyroxad)、(2.008)福拉比(furametpyr)、(2.009)異丙噻菌胺(isofetamid)、(2.010)吡唑萘菌胺(isopyrazam)(反側-表異構物之鏡像異構物1R,4S,9S)、(2.011)吡唑萘菌胺(反側-表異構物之鏡像異構物1S,4R,9R)、(2.012)吡唑萘菌胺(反側-表異構物之消旋物1RS,4SR,9SR)、(2.013)吡唑萘菌胺(同側-表異構物之消旋物1RS,4SR,9RS和反側-表異構物之消旋物1RS,4SR,9SR的混合物)、(2.014)吡唑萘菌胺(同側-表異構物之鏡像異構物1R,4S,9R)、(2.015)吡唑萘菌胺(同側-表異構物之鏡像異構物1S,4R,9S)、(2.016)吡唑萘菌胺(同側-表異構物消旋物之1RS,4SR,9RS)、(2.017)氟唑菌苯胺(penflufen)、(2.018)吡噻菌胺(penthiopyrad)、(2.019)吡福密芬(pydiflumetofen)、(2.020)必拉氟密(Pyraziflumid)、(2.021)環丙吡菌胺(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(2.025)1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)聯苯-2-基]-1H-吡唑-4-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-環丙基-5-氟苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.035)N-(2-三級-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-甲醯胺、(2.036)N-(2-三級-丁基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(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-甲醯胺、(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-甲醯胺、(2.039)N-[(1R,4S)-9-(二氯亞甲基)-1,2,3,4-四氫-1,4-亞甲基萘(methanonaphthalen)-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.040)N-[(1S,4R)-9-(二氯亞甲基)-1,2,3,4-四氫-1,4-亞甲基萘(methanonaphthalen)-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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(carbothioamide)、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺、(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-甲醯胺。
3)於複合物III的呼吸鏈之抑制劑,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)賽座滅(cyazofamid)、(3.007)醚菌胺(dimoxystrobin)、(3.008)烯肟菌酯(enoxastrobin)、(3.009)凡殺同(famoxadone)、(3.010)咪唑菌酮(fenamidone)、(3.011)氟菌蟎酯(flufenoxystrobin)、(3.012)氟嘧菌酯(fuoxastrobin)、(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)百克敏(pyraclostrobin)、(3.018)唑胺菌酯(pyrametostrobin)、(3.0019)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]oxy}-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-1,5-二氧雜環壬烷(dioxonan)-7-基酯、(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]oxy}-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-甲基苯甲基}胺甲酸甲酯。
4)有絲分裂及細胞分裂抑制劑,例如(4.001)多菌靈(carbendazim)、(4.002)乙黴威(diethofencarb)、(4.003)噻唑菌胺(ethaboxam)、(4.004)氟吡菌胺(fluopicolide)、(4.005)賓克隆(pencycuron)、(4.006)腐絕(thiabendazole)、(4.007)甲基多保淨(thiophanate-methyl)、(4.008)座賽胺(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)具有多部位活性之化合物,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)環烷酸銅、(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(dodine)、(5.012)福爾培(folpet)、(5.013)鋅錳乃浦(mancozeb)、(5.014)錳乃浦(maneb)、(5.015)免得爛(metiram)、(5.016) 免得爛鋅(metiram zinc)、(5.017)快得寧(oxine-copper)、(5.018)甲基鋅乃浦(propineb)、(5.019)硫和包括多硫化鈣之硫製劑、(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-吡咯并[3',4':5,6][1,4]二硫雜環己并(dithiino)[2,3-c][1,2]噻唑-3-甲腈。
6)能夠觸發宿主防禦之化合物,例如(6.001)阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、(6.002)異噻菌胺(isotianil)、(6.003)撲殺熱(probenazole)、(6.004)噻醯菌胺(tiadinil)。
7)胺基酸及/或蛋白質生物合成抑制劑,例如(7.001)賽普洛(cyprodinil)、(7.002)嘉賜黴素(kasugamycin)、(7.003)嘉賜黴素鹽酸鹽水合物、(7.004)氧四環素(oxytetracycline)、(7.005)派美尼(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產生抑制劑,例如(8.001)矽噻菌胺(silthiofam)。
9)細胞壁合成抑制劑,例如(9.001)苯噻菌胺(benthiavalicarb)、(9.002)達滅芬(dimethomorpH),(9.003)氟嗎啉(flumorpH),(9.004)丙森鋅(iprovalicarb)、(9.005)雙炔醯菌胺(mandipropamid)、(9.006)丁吡嗎啉(pyrimorpH),(9.007)纈菌胺(valifenalate)、(9.008)(2E)-3-(4-三級-丁基苯基)-3-(2-氯吡啶-4-基)-1-(嗎福林-4-基)丙-2-烯-1-酮、(9.009)(2Z)-3-(4-三級-丁基苯基)-3-(2-氯吡啶-4-基)-1-(嗎福林-4-基)丙-2-烯-1-酮。
10)脂質及膜合成抑制劑,例如(10.001)普拔克(propamocarb)、(10.002)普拔克鹽酸鹽、(10.003)脫克松(tolclofos-methyl)。
11)黑色素生物合成抑制劑,例如(11.001)三環唑(tricyclazole),(11.002){3-甲基-1-[(4-甲基苯甲醯)胺基]丁-2-基}胺基甲酸2,2,2-三氟乙基酯。
12)核酸合成抑制劑,例如(12.001)本達樂(benalaxyl)、(12.002)本達樂-M(克拉昔(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)可充當非偶合劑之化合物,例如(14.001)扶吉胺(fluazinam)、(14.002)敵蟎普(meptyldinocap)。
15)其他化合物,例如(15.001)脫落酸(abs順-ic acid)、(15.002)苯噻硫氰(ben噻唑e)、(15.003)苯噻嗪(bethoxazin)、(15.004)卡巴西黴素(capsimycin)、(15.005)香芹酮(carvone)、(15.006)滅蟎猛(chinomethionat)、(15.007)硫雜靈(cufraneb)、(15.008)環氟菌胺(cyflufenamid)、(15.009)克絕(cymoxanil)、(15.010)環丙磺醯胺(cyprosulfamide)、(15.011)氟噻菌淨(flutianil)、(15.012)福賽得(fosetyl-aluminium)、(15.013)福賽得-鈣(fosetyl-calcium)、(15.014)福賽得-鈉(fosetyl-sodium)、(15.015)異硫氰酸甲酯、(15.016)滅芬農(metrafenon)、(15.017)米多黴素(mildiomycin)、(15.018)納他黴素(natamycin)、(15.019)二甲基二硫胺基甲酸鎳、(15.020)酞菌酯(nitrothal-異丙基)、(15.021)歐莫克(oxamocarb)、(15.022)氟噻唑吡乙酮(Oxathiapiprolin)、(15.023)歐芬英(oxyfenthiin)、(15.024)五氯酚(penta氯phenol)及鹽、(15.025)亞磷酸(phosphorous acid)及其鹽、(15.026)普拔克-乙膦酸鹽(propamocarb-fosetylate)、(15.027)比芬酮(pyriofenone)(克芬酮(chlazafenone))、(15.028)特布洛昆(tebufloquin)、(15.029)克枯爛(tecloftalam)、(15.030)甲磺菌胺(tolnifanide)、(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}哌啶-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}哌啶-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]二硫雜環己并(dithiino)[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-基氧基)苯基]-4,5-二氫-1,2-唑-3-基}-1,3-噻唑-2-基)哌啶-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-基氧基)苯基]-4,5- 二氫-1,2-唑-3-基}-1,3-噻唑-2-基)哌啶-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-基氧基)苯基]-4,5-二氫-1,2-唑-3-基}-1,3-噻唑-2-基)哌啶-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}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-唑-5-基}-3-氯苯基酯、(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}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-唑-5-基}-3-氯苯基酯、(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}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-唑-5-基}-3-氯苯基酯、(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}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-唑-5-基}苯基酯、(15.045)2-苯基酚及其鹽、(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-3,4-二氫異喹啉-1-基)喹啉、(15.048)4-胺基-5-氟嘧啶-2-醇(互變異構形式: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-磺酸基(sulfono)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-苯并氧雜氮呯、(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-基酯、(15.056)(2Z)-3-胺基-2-氰基-3-苯基丙烯酸乙基酯、(15.057)啡-1-甲酸、(15.058)3,4,5-三羥基苯甲酸丙基酯、(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}胺甲酸三級-丁基酯、(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。
式(I)化合物可與生物除害劑組合。
生物除害劑特別是包括細菌、真菌、酵母、植物萃取物和由微生物形成的產物,包括蛋白質和次級代謝物。
生物除害劑包括細菌諸如形成孢子的細菌、定殖根的細菌和充當生物殺蟲劑、殺真菌劑或殺線蟲劑之細菌。
該用作或可用作生物除害劑之細菌的實例為:芽孢枯草桿菌(Bacillus amyloliquefaciens),菌株FZB42(DSM 231179)、或蠟狀芽孢桿菌(Bacillus cereus),尤其是蠟狀芽孢桿菌(B.cereus)菌株CNCM I-1562或堅固芽孢桿菌(Bacillus firmus),菌株I-1582(登錄號CNCM I-1582)或短小芽孢桿菌(Bacillus pumilus),尤其是菌株GB34(登錄號ATCC 700814)及菌株QST2808(登錄號NRRL B-30087)、或枯草桿菌(Bacillus subtilis),尤其是菌株GB03(登錄號ATCC SD-1397)、或枯草桿菌(Bacillus subtilis)菌株QST713(登錄號NRRL B-21661)或枯草桿菌(Bacillus subtilis)菌株OST 30002(登錄號NRRL B-50421)、蘇力菌(Bacillus thuringiensis),尤其是蘇力菌以色列亞種(B.thuringiensis subspecies israelensis)(血清型H-14)、菌株AM65-52(登錄號ATCC 1276)、或蘇力菌鮎澤亞種(B.thuringiensis subsp.aizawai),尤其是菌株ABTS-1857(SD-1372)、或蘇力菌庫斯克亞種(B.thuringiensis subsp.kurstaki strain)菌株HD-1、或蘇力菌擬步行蟲亞種(B.thuringiensis subsp.tenebrionis)菌株NB 176(SD-5428)、穿刺巴氏桿菌(Pasteuria penetrans)、巴氏桿菌屬(Pasteuria spp.)(腎狀腎形線蟲(Rotylenchulus reniformis)線蟲)-PR3(登錄號ATCC SD-5834)、細黃鏈黴菌(Streptomyces microflavus)菌株AQ6121(=QRD 31.013、NRRL B-50550)、鮮黃鏈黴菌(Streptomyces galbus)菌株AQ 6047(登錄號NRRL 30232)。
用作或可用作生物除害劑之真菌和酵母的實例為:巴氏蠶白僵菌(Beauveria bassiana),特別是菌株ATCC 74040、微坦盾殼黴(Coniothyrium minitans),特別是CON/M/91-8菌株(登錄號DSM-9660)、輪枝菌屬(Lecanicillium spp.),特別是菌株HRO LEC 12、臘蚧輪枝菌(Lecanicillium lecanii,以前稱為臘蚧輪刺孢菌(Verticillium lecanii)),特別是菌株KV01、黑殭菌(Metarhizium anisopliae),特別是 菌株F52(DSM3884/ATCC 90448)、梅奇酵母(Metschnikowia fructicola),特別是菌株NRRL Y-30752、玫煙色擬青黴菌(Paecilomyces fumosoroseus)、(現:玫煙色棒束孢(Isaria fumosorosea)),特別是菌株IFPC 200613、或菌株Apopka 97(登錄號ATCC 20874)、淡紫擬青黴菌(Paecilomyces lilacinus),特別是淡紫擬青黴菌菌株251(AGAL 89/030550)、黃籃狀菌(Talaromyces flavus),特別是菌株V117b、深綠木黴(Trichoderma atroviride),特別是菌株SC1(登錄號CBS 122089)、哈茨木黴菌(Trichoderma harzianum),特別是T.harzianum rifai T39.(登錄號CNCM I-952)。
用作或可用作生物除害劑之病毒的實例為:茶姬捲葉蛾(Adoxophyes orana)(夏季水果捲葉蛾)顆粒增殖病毒(GV)、蘋果蠹蛾(Cydia pomonella)(蘋果小捲蛾)顆粒增殖病毒(GV)、蕃茄夜蛾(Helicoverpa armigera,棉鈴蟲)核多角體病毒(NPV)、甜菜葉蛾(Spodoptera exigua)(甜菜夜蛾)mNPV、草地夜蛾(Spodoptera frugiperda)(秋夜蛾)mNPV、海灰翅夜蛾(Spodoptera littoralis)(非洲棉葉蟲)NPV。
亦包括者為以‘接種物‘加至植物或植物部份或植物器官且由於彼等的特定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)、固氮螺旋菌屬(Azospirillum spp.)、固氮菌屬(Azotobacter spp.)、慢生根瘤菌屬(Bradyrhizobium spp.)、伯克氏菌屬(Burkholderia spp.),特別是洋蔥伯克氏菌(Burkholderia cepacia)(以前稱為蔥頭假單孢菌(Pseudomonas cepacia))、巨孢囊黴屬(Gigaspora spp.)或單孢巨孢囊霉(Gigaspora monosporum)、球囊黴屬(Glomus spp.)、蠟蘑屬(Laccaria spp.)、布氏乳酸桿菌(Lactobacillus buchneri)、類球囊黴屬(Paraglomus spp.)、彩色豆馬勃(Pisolithus tinctorus)、假單孢菌屬(Pseudomonas spp.)、根瘤菌屬(Rhizobium spp.),特別是三葉草根瘤菌(Rhizobium trifolii)、根鬚腹菌屬(Rhizopogon spp.)、硬皮馬勃屬(Scleroderma spp.)、黏蓋菌屬(Suillus spp.)、鏈黴菌屬(Streptomyces spp.)。
用作或可用作生物除害劑之植物萃取物和由微生物形成的產物(包 括蛋白質和次級代謝物)的實例為:大蒜(Allium sativum)、苦艾(Artemisia absinthium)、印楝素(azadirachtin)、Biokeeper WP、黑肉桂(Cassia nigricans)、苦皮藤(Celastrus angulatus)、土荊芥(Chenopodium anthelminticum)、甲殼素(chitin)、Armour-Zen、歐洲鱗毛蕨(Dryopteris filix-mas)、問荊(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(藜麥皂素萃取物)、除蟲菊/除蟲菊酯、苦木(Quassia amara)、櫟(Quercus)、皂樹皮(Quillaja)、Regalia、〝RequiemTM殺蟲劑〞、魚藤酮、魚尼丁(ryania)/藍尼定(ryanodine)、康福利草(Symphytum officinale)、菊蒿(Tanacetum vulgare)、百里酚、Triact 70;TriCon、旱金蓮(Tropaeulum majus)、異株蕁麻(Urtica dioica)、藜蘆鹼(Veratrin)、槲寄生(Viscum album)、十字花科萃取物,尤其是油菜籽粉或芥末粉。
式(I)化合物可與安全劑(例如解草酮(benoxacor)、解毒喹(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、環丙磺醯胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole)(-乙基)、解草啶(fenclorim)、解草胺(flurazole)、肟草安(fluxofenim)、解草唑(furilazole)、異地芬(isoxadifen)(-乙基)、吡唑解草酯(mefenpyr)(-二乙基)、萘二甲酸酐、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)組合。
可根據本發明處理整株植物和植物部份。植物在此係理解為意指所有的植物及植物群,諸如所欲及非所欲野生植物或作物植物(包括天然存在的作物),例如穀類(小麥、稻米、黑小麥、大麥、黑麥、燕麥)、玉米、大豆、馬鈴薯、甜菜、甘蔗、蕃茄、甜椒、黃瓜、甜瓜、胡蘿蔔、西瓜、洋蔥、萵苣、菠菜、韭菜、豆子、甘藍(例如高麗菜)和其他蔬菜種類、棉花、煙草、油菜,及亦指果實植物(該等果實為蘋果、梨、柑橘類水果和葡萄)。作物植物可為可藉由習知的育種及優化方法或藉 由生物技術和基因工程方法或該等方法的組合獲得之植物,包括基因轉殖植物且包括受到或未受到植物育種家權利(plant breeders’ rights)保護的植物栽培品種。植物係應理解為意指所有的發育期諸如種子、幼苗、幼小(未成熟)植物、接近於且包括成熟植物。植物係應理解為意指植物在地上與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、針葉、梗、莖、花、果實體、果實和種子,且亦指根、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無性和有性繁殖材料,例如插條、塊莖、根莖、分株和種子。
本發明用式(I)化合物處理植物和植物部份係以習知處理方法(例如藉由浸漬、噴灑、蒸發、氣霧化、散播、塗上、注射,及在繁殖材料的情況下,尤其是在種子的情況下,亦藉由塗敷一或多層塗層)直接進行或藉由使化合物作用於其周圍、棲息地或貯藏空間來進行。
如上文已提及者,根據本發明可能處理整株植物或其部份。在一較佳實施態樣中,處理野生植物種類及植物栽培品種、或彼等經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,及其部份。在另一較佳實施態樣中,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和植物栽培品種(基因改造生物)及其部份。術語“部份”或“植物的部份”或“植物部份”已於上文解釋。根據本發明特佳者為處理個別市售習知的植物栽培品種或彼等使用中的植物。植物栽培品種係理解為意指具有新性質(「性狀」)且已藉由習知的育種、藉由突變誘發或藉由重組DNA技術獲得的植物。彼等可為栽培品種、變種、生物型或基因型。
欲根據本發明處理之較佳基因轉殖植物或植物栽培品種(藉由基因工程獲得者)包括所有透過基因改造而接受賦與這些植物特別有利的有用性質("性狀")之遺傳物質的植物。該等性質的實例為較佳的植物生長、對高或低溫之耐受性增加、對乾旱或水位或土壤鹽度的耐受性增加、開花性能提高,較易收成、加速熟成,較高之收穫率、收穫產物之較高品質及/或較高營養價值、收穫產物之較佳儲存壽命及/或加工性。該等性質之其他且特別強調的實例為由於(例如)在植物內所形成之毒素, 特別是彼等由來自蘇力菌(Bacillus thuringiensis)之遺傳物質(例如由基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF以及其組合)於植物內所形成之毒素而植物對抗動物和微生物害蟲(諸如昆蟲、蜘蛛、線蟲、蟎、蛞蝓和蝸牛)之抗性增加,以及(例如)由後天性系統抗性(SAR)、系統素(systemin)、植物防禦素、激發子(elicitors)和抗性基因及對應表現之蛋白質和毒素所引起之植物對抗植物病原性真菌、細菌及/或病毒的抗性增加,以及植物對某些除草活性化合物(例如咪唑啉酮類、磺醯脲類、草甘膦(glyphosate)或草胺膦(phosphinothricin))(例如"PAT"基因)之耐受性增加。賦予討論中的所要性狀之基因亦可彼此組合存在於基因轉殖植物中。基因轉殖植物的實例包括重要作物,諸如穀類(小麥、稻米、黑小麥、大麥、黑麥、燕麥)、玉米、大豆、馬鈴薯、甜菜、甘蔗、番茄、豌豆及其他蔬菜類型、棉花、菸草、油菜以及果實植物((該等果實為蘋果、梨、柑橘類水果和葡萄藤),特別強調者為玉米、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(“性狀”)為植物對昆蟲、蜘蛛、線蟲和蛞蝓和蝸牛之抗性增加。
以式(I)化合物處理植物和植物部份係使用習知的處理方法(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)、滴液灌溉,及在繁殖物質之情形下,特別是在種子之情形下,另外藉由乾式種子處理、液態種子處理、漿液處理、藉由包覆、藉由塗上一或多層等等)直接進行或藉由作用在其周圍、棲息地或貯藏空間來進行。此外可能以超低體積法施用式(I)化合物,或以施用形式或式(I)化合物本身注入土壤中。
植物之較佳直接處理為葉施用,意指將式(I)化合物施用於葉子,其中處理頻率及施用率應根據討論中的害蟲之感染程度來調整。
在系統性活性成分的情況下,式(I)化合物亦經由根系統進入植物。接著藉由式(I)化合物作用於植物棲息地來處理植物。此可例如藉由澆灌或藉由混入土壤或營養液中達成,意指以液體形式的式(I)化合物浸透植物之所在地(例如,土壤或水耕系統),或藉由土壤施用,意指根據 本發明之式(I)化合物以固體形式(例如,於粒劑形式)引入植物之所在地達成。在水稻作物的情況下,此亦可藉由將式(I)化合物以固體施用形式(例如,呈粒劑)計量供給至浸水稻田中而達成。
藉由處理植物種子來控制動物害蟲是早已知道的且為不斷改良之標的。然而,種子的處理導致一系列總是無法以令人滿意的方式解決之問題。因此,希望開發出在貯藏期間、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用除害劑以保護種子及發芽植物之方法。另外希望將所使用的活性成分之量最佳化,以便對種子及發芽植物提供最佳保護而免於受到動物害蟲的攻擊,但是所使用的活性成分不傷害植物本身。特別地,用於處理種子之方法亦應考慮抗害蟲性或耐害蟲性基因轉殖植物之固有的殺蟲或殺線蟲性質,以便以最少支出的除害劑達成對種子以及發芽植物的最佳保護。
本發明因此亦關於一種藉由以式(I)化合物中之一者處理種子來防止種子及發芽植物受到害蟲攻擊之方法。用於防止種子及發芽植物受到害蟲攻擊之根據本發明方法另外包含一種其中以式(I)化合物及混合組分以一次操作同時處理或相繼處理種子之方法。亦另外包含一種其中於不同的時間以式(I)化合物及混合組分處理種子之方法。
本發明亦關於式(I)化合物用於處理種子以防止種子及所得植物的動物害蟲之用途。
本發明另外關於已用根據本發明之式(I)化合物處理以防止動物害蟲之種子。本發明亦關於已同時用式(I)化合物及混合組分處理之種子。本發明另外關於已在不同時間用式(I)化合物及混合組分處理之種子。在種子已於不同時間用式(I)化合物及混合組分處理之情形下,個別物質可以不同的層存在於種子上。在此情形下,包含式(I)化合物及混合組分的層可視情況地以中間層分開。本發明亦關於其中式(I)化合物及混合組分已施用作為塗層的一部分或作為除了塗層以外的另一層或更多層之種子。
本發明另外關於在以式(I)化合物處理之後進行塗膜方法以防止在種子上的灰塵磨耗之種子。
當式(I)化合物的系統性作用時所出現的優點之一為種子之處理不只防止種子本身的動物害蟲,且亦在出苗之後,防止由種子所產生之植物的動物害蟲。以此方式,可免除在播種時或不久之後對作物的立即處理。
另一優點為以式(I)化合物處理種子可提高所處理之種子的發芽及出苗。
同樣被視為優點的是式(I)化合物尤其也可用於基因轉殖種子。
此外,式(I)化合物可與傳訊技術之組成物組合使用,其導致共生體(諸如(例如)根瘤菌、菌根及/或內生性細菌或真菌)更好的選殖,及/或導致最佳化固氮作用。
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。更具體地說,此為下列之種子:穀類(例如小麥、大麥、黑麥、小米和燕麥)、玉米、棉花、大豆、稻米、馬鈴薯、向日葵、咖啡、菸草、油菜籽、油菜、甜菜(例如,糖用甜菜和飼料甜菜)、花生、蔬菜類(例如,番茄、胡瓜、豆類、十字花科蔬菜、洋蔥和萵苣)、水果植物、草皮及觀賞植物。特別重要的是處理穀類(諸如小麥、大麥、黑麥和燕麥)、玉米、大豆、棉花、油菜籽、油菜和稻米之種子。特別重要的是穀類(諸如小麥、大麥、黑麥和燕麥)、玉米、大豆、棉花、油菜籽、油菜、蔬菜和稻米之種子的處理。
如上文已提及者,以式(I)化合物處理基因轉殖種子也是特別重要的。此包括通常含有至少一種特別是控制表現具有殺蟲及/或殺線蟲性質的多肽之異源基因的植物種子。基因轉殖種子中的異源基因可源自諸如下列之微生物:例如桿菌(Bacillus)、根瘤菌(Rhizobium)、假單胞菌(Pseudomonas)、沙雷氏菌(Serratia)、木黴菌(Trichoderma)、棒狀桿菌(Clavibacter)、球囊黴(Glomus)、或黏帚黴(Gliocladium)。本發明係特別適合於處理含有至少一種源自桿菌屬之異源基因的基因轉殖種子。異源基因更較佳係源自蘇力菌。
在本發明的情況下,式(I)化合物係施用至種子。該種子較佳係以其足夠穩定以在處理過程中不發生損害的狀態下來處理。通常,種子可在採收和播種之間的任何時間點處理。習慣上使用已經從植物中分 離並已去除果實的穗軸、殼、柄、表皮、毛或果肉的種子。例如,可能使用已收成、清洗且乾燥至允許儲存之水分含量的種子。或者,亦可能使用在乾燥之後已用例如水處理且接著再乾燥(例如滲調處理(priming))之種子。在水稻種子的情況下,也可能使用已經在(例如)水中浸泡至稻米胚芽之某期(雞胸期(pigeon breast stage))以刺激發芽及更均勻的出苗之種子。
當處理種子時,通常必須以種子發芽不會受到不利影響或不傷害所得植物之方式小心選擇式(I)化合物施用至種子的量及/或另外的添加劑之量。在活性成分於某些施用率下會呈現植物毒性作用之情形下,必須特別確保如此。
通常,式(I)化合物係以適當配製物之形式施用至種子。用於種子處理的適當配製物及方法為熟習該項技術者已知的。
式(I)化合物可轉化成習知拌種配製物,諸如溶液、乳劑、懸浮液、粉末、發泡體、漿液或用於種子的其他塗覆組成物,以及ULV配製物。
此等配製物係以已知方式藉由將式(I)化合物與習知添加劑(例如,習知增量劑以及溶劑或稀釋劑、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、以及水)混合而製得。
可存在於根據本發明可使用之拌種配製物中的染料為習知用於該等目的之所有染料。可能使用微溶於水中的顏料,或可溶於水的染料。實例包括以羅丹明B、C.I.顏料紅色112號、和C.I.溶劑紅色1號為名的染料。
可存在於根據本發明可使用之拌種配製物中的有用潤濕劑為促進潤濕且習知用於活性農化成分之配製物的所有物質。可優先使用萘磺酸烷酯,諸如萘磺酸二異丙酯或二異丁酯。
可存在於根據本發明可使用之拌種配製物中的適當分散劑及/或乳化劑為習知用於活性農化成分之配製物的所有非離子、陰離子和陽離子分散劑。可優先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。適當非離子分散劑尤其包括環氧乙烷/環氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基酚聚乙二醇醚及其磷酸化或硫酸化衍生物。適當陰離子分散劑尤其為木質素磺酸鹽、聚丙烯酸鹽和芳 基磺酸鹽-甲醛縮合物。
可存在於根據本發明可使用之拌種配製物中的消泡劑為習知用於活性農化成分之配製物的所有泡沫抑制物質。可優先使用聚矽氧消泡劑與硬脂酸鎂。
可存在於根據本發明可使用之拌種配製物中的防腐劑為就該等目的可使用於農化組成物中之所有物質。實例包括雙氯酚及苯甲基醇半縮甲醛。
可存在於根據本發明可使用之拌種配製物中的二次增稠劑為就該等目的可使用於農化組成物中之所有物質。較佳實例包括纖維素衍生物、丙烯酸衍生物、三仙膠、改質黏土及細粉狀矽氧。
可存在於根據本發明可使用之拌種配製物中的黏著劑為所有可用於拌種產品之習用黏合劑。較佳的實例包括聚乙烯基吡咯啶酮、聚乙酸乙烯酯、聚乙烯醇和泰勒膠(tylose)。
可存在於根據本發明可使用之拌種配製物中的赤黴素較佳為赤黴素A1、A3(=赤黴酸)、A4和A7;特佳者為使用赤黴酸。赤黴素為已知的(參考R.Wegler "Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel",vol.2,Springer Verlag,1970,pp.401-412)。
根據本發明可用的拌種配製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,濃縮物或以水稀釋而可自其獲得的製劑可用於拌塗穀類(諸如小麥、大麥、黑麥、燕麥和黑小麥)之種子,以及玉米、稻米、油菜、豌豆、豆子、棉花、向日癸、大豆和甜菜之種子,或其他各種廣泛不同種類的蔬菜種子。根據本發明可用的拌種配製物,或其稀釋使用形式亦可用於拌塗基因轉殖植物之種子。
關於以根據本發明可用的拌種配製物或經由添加水而自其製備的使用形式處理種子,可使用習知可用於拌種的所有混合單元。具體地說,拌種中的程序為以分批或連續地操作將種子放入混合器中,添加特定的所欲量之拌種配製物(以其原樣子或事先以水稀釋之後)且混合,直到該配製物均勻地分佈於種子上為止。若適當時,此接著乾燥操作。
根據本發明可用的拌種配製物之施用率可在相當寬廣的範圍內改 變。施用率係受到配製物中式(I)化合物的特定含量及種子所支配。式(I)化合物之施用率通常係每公斤種子介於0.001和50g之間,較佳為每公斤種子介於0.01和15g之間。
在動物健康領域中,亦即在獸醫領域中,式(I)化合物具有對抗動物寄生蟲(特別是體外寄生蟲或體內寄生蟲)的活性。術語"體內寄生蟲"尤其包括蠕蟲及原生動物,諸如球蟲。體外寄生蟲典型且較佳地為節肢動物,特別是昆蟲或螨。
在獸醫領域中,具有有利的溫血動物毒性之式(I)化合物適合於控制出現在動物育種和畜牧業的家畜、育種動物、動物園動物、實驗室動物、實驗動物和家養動物中的寄生蟲。彼等具有對抗所有或特定發育期之寄生蟲的活性。
農業家畜包括(例如)哺乳動物諸如綿羊、山羊、馬、驢、駱駝、水牛、兔、馴鹿、黇鹿,且尤其是牛和豬;或家禽諸如火雞、鴨、鵝、且尤其是雞;例如水產養殖之魚和甲殼類動物;或例如於水產養殖中之魚或甲殼動物,或視情況而定可為昆蟲,諸如蜜蜂。
家養動物包括(例如)哺乳類動物,諸如倉鼠、天竺鼠、大鼠、小鼠、絨鼠、雪貂、或特別是狗、貓;籠中鳥;爬蟲類;兩棲類和觀賞魚。
在一特定實施態樣中,式(I)化合物係投予至哺乳動物。
在另一特定實施態樣中,式(I)化合物係投予至鳥類,亦即籠中鳥且特別是家禽。
使用式(I)化合物控制動物寄生蟲係意欲減少或防止病症、死亡個案和性能降低(在肉、奶、羊毛、皮革、蛋、蜂蜜等等的情況下),致使能夠更經濟和更簡單地飼育動物且可達成更好的動物福利。
關於動物健康領域,術語"控制(control)或(controlling)"在本情況下意指式(I)化合物將在感染該等寄生蟲的動物中之特定寄生蟲的發生率有效地減少至無害程度。更明確地說,"控制(controlling)"本情況下意指式(I)化合物殺死個別寄生蟲、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)之目,例如,血蝨屬(Haematopinus spp.)、長 齶蝨屬(Linognathus spp.)、蝨屬(Pediculus spp.)、陰蝨屬(Phtirus spp.)、牛蝨屬(Solenopotes spp.);來自食毛目(Mallophagida)及鈍角亞目(Amblycerina)與絲角亞目(Ischnocerina)之目,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.)、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)以及長角亞目(Nematocerina)與短角亞目(Brachycerina)之目,例如,斑蚊屬(Aedes spp.)、瘧蚊屬(Anopheles spp.)、黄虻屬(Atylotus spp.)、蜂蝨蠅屬(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.)、馬蠅屬(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.)、牛蠅屬(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.)、牛虻屬(Tabanus spp.)、大蚊屬(Tipula spp.)、維蚋屬(Wilhelmia spp.)、污蠅屬(Wohlfahrtia spp.);來自蚤目(Siphonapterida)之目,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)之目,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)之目的滋擾和衛生性害蟲。
另外,在節肢動物的情況下,應以實例而非限制之方式提及下列蜱蟎亞綱: 來自蜱蟎亞綱(Acari(Acarina))之亞綱及後氣門亞目(Metastigmata)之目,例如,來自軟蜱科(argasidae)之科,如銳緣蜱屬(Argas spp.)、鈍緣蜱屬(Ornithodorus spp.)、耳蜱屬(Otobius spp.),來自硬蜱科(Ixodidae)之科,如大壁蝨屬(Amblyomma spp.)、革蜱屬(Dermacentor spp.)、血蜱屬(Haemophysalis spp.)、長鬚壁蝨屬(Hyalomma spp.)、硬蜱屬(Ixodes spp.)、扇頭壁蝨屬(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)之目,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.)、小蜂蟎屬(Tropilaelaps spp.)、瓦蟎屬(Varroa spp.);來自輻蟎亞目(Actinedida)(前氣門亞目(Prostigmata))之目,例如蟎屬(Acarapis spp.)、姬螯蟎屬(Cheyletiella spp.)、毛囊蟎屬(Demodex spp.)、牦蟎屬(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))之目,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(Laminosioptes 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:鞭毛蟲綱(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.)、五毛滴蟲屬(Pentatrichomonas spp.)、四毛滴蟲屬(Tetratrichomonas spp.)、滴蟲屬(Trichomonas spp.)、三毛滴蟲屬(Tritrichomonas spp.)。
眼蟲門(Euglenozoa):來自錐蟲科(Trypanosomatida)(例如利什曼屬 (Leishmania spp.)、錐蟲屬(Trypanosoma spp.)。
肉鞭毛蟲門(Sarcomastigophora)(根足綱(Rhizopoda))諸如內阿米巴科(Entamoebidae)(例如內阿米巴屬(Entamoeba spp.)、Centramoebidae,例如棘阿米巴屬(Acanthamoeba sp.)、Euamoebidae,例如哈氏阿米巴屬(Hartmanella sp.)。
囊泡蟲類(Alveolata)諸如頂覆門(Apicomplexa)(孢子蟲綱(Sporozoa)):例如隱孢子蟲屬(Cryptosporidium spp.);來自艾美球蟲目(Eimeriida)之目,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.)、哈蒙屬(Hammondia spp.)、同形球蟲屬(Isospora spp.)、新孢球蟲屬(Neospora spp.)、肉孢子蟲屬(Sarcocystis spp.)、弓蟲屬(Toxoplasma spp.);來自阿德雷德目(Adeleida)之目,例如,肝簇蟲屬(Hepatozoon spp.)、真球蟲屬(Klossiella spp.);來自血孢子蟲目(Haemosporida)之目,例如,住血白冠病孢子蟲屬(Leucocytozoon spp.)、瘧原蟲屬(Plasmodium spp.);來自梨形目(Piroplasmida)之目,例如,焦蟲屬(Babesia spp.)、纖毛蟲屬(Ciliophora spp.)、Echinozoon屬、泰勒原蟲屬(Theileria spp.);來自Vesibuliferida之目,例如,纖毛蟲屬(Balantidium spp.)、布克斯頓纖毛蟲屬(Buxtonella spp.)。
微孢子蟲(Microspora)諸如腦胞內原蟲屬(Encephalitozoon spp.)、腸內微孢子蟲屬(Enterocytozoon spp.)、球孢子蟲屬(Globidium spp.)、孢子蟲屬(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(nematodes)、舌形動物門(Pentastoma)及扁形動物門(Platyhelmintha)(例如單殖目(monogenea)、絛蟲(cestodes)及吸蟲(trematodes))。
例示性蠕蟲包括但不限於:單殖目(Monogenea):例如:指環蟲屬(Dactylogyrus spp.)、三代蟲屬(Gyrodactylus spp.)、同盤吸蟲屬(Microbothrium spp.)、多盤吸蟲屬(Polystoma spp.)、Troglocephalus spp.;絛蟲:來自擬葉目(Pseudophyllidea)之目,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.)、呦蟲屬(Ichthyobothrium spp.)、舌狀絛蟲屬(Ligula spp.)、裂頭絛蟲屬(Schistocephalus spp.)、螺旋絛蟲屬(Spirometra spp.)。
來自圓葉目(Cyclophyllida)之目,例如:德里絛蟲屬(Andyra spp.)、裸頭絛蟲屬(Anoplocephala spp.)、無卵黄腺絛蟲屬(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.)、棘鳞絛蟲屬(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:來自複殖目(Digenea)之目,例如:澳畢吸蟲屬(Austrobilharzia spp.)、短咽吸蟲屬(Brachylaima spp.)、杯殖吸蟲屬(Calicophoron spp.)、下彎吸蟲屬(Catatropis spp.)、支睪吸蟲屬(Clonorchis spp.)、肛瘤吸蟲屬(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.)、薑片蟲屬(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.)、異形吸蟲屬(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.)、隱孔吸蟲屬(Nanophyetus spp.)、背孔吸蟲屬(Notocotylus spp.)、後睪吸蟲屬(Opisthorchis spp.)、鳥畢吸蟲屬(Ornithobilharzia spp.)、肺吸蟲屬 (Paragonimus spp.)、副雙口吸蟲屬(Paramphistomum spp.)、斜睾吸蟲屬(Plagiorchisspp.)、莖雙穴吸蟲屬(Posthodiplostomum spp.)、前殖吸蟲屬(Prosthogonimus spp.)、血吸蟲屬(Schistosoma spp.)、毛畢屬(Trichobilharzia spp.)、鮭吸蟲屬(Troglotrema spp.)、盲腔吸蟲屬(Typhlocoelum spp.)。
線蟲:來自毛形線蟲亞目(Trichinellida)之目,絲蟲屬(Capillaria spp.)、旋毛蟲屬(Trichinella spp.)、Trichomosoides屬、鞭蟲屬(Trichuris spp.)。來自墊刃目(Tylenchida)之目,例如:細絲鯰屬(Micronema spp.)、Parastrangyloides屬、糞桿線蟲屬(Strongyloides spp.)。
來自小桿目(Rhabditida)之目,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.)。
來自旋尾目(Spirurida)之目,例如:棘唇屬(Acamthocheilonema 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屬、毛體線蟲屬(Crassicauda spp.)、雙瓣絲蟲屬(Dipetalonema spp.)、心絲蟲屬(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.)、Probstmayria屬、Pseudofilaria屬、腹腔絲蟲屬(Setaria spp.)、Skjrabinema屬、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.)、弓蛔線蟲屬(Toxascaris spp.)、弓首蛔蟲屬(Toxocara spp.)、吳策線蟲屬(Wuchereria spp.)。
棘頭動物門(Acantocephala):來自寡棘吻目(Oligacanthorhynchida)之目,例如:巨吻棘頭蟲屬(Macracanthorhynchus spp.)、前睪棘頭蟲屬(Prosthenorchis spp.);來自念珠目(Moniliformida)之目,例如:念珠棘頭蟲屬(Moniliformis spp.);來自多形目(Polymorphida)之目,例如:細頸棘頭蟲屬(Filicollis spp.);來自棘吻目(Echinorhynchida)之目,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):來自舌形蟲目(Porocephalida)之目,例如,舌形蟲屬(Linguatula spp.)。
在獸醫領域及畜牧業中,式(I)化合物係藉由該項技術中通常已知的方法(諸如經由經腸、非經腸、經皮膚或經鼻途徑)以適當製劑的形式投予。投予可為預防性地、補救預防性(metaphylactic)或治療性。
因此,本發明之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。
本發明之另一特定態樣關於用作為驅蟲劑(尤其是作為殺線蟲劑、殺扇形動物劑(platyxelminthicide)、殺棘頭動物劑(acanthocephalicide)或殺舌形動物劑(pentastomicide))之式(I)化合物。
本發明另一特定態樣關於用作為抗原蟲劑之式(I)化合物。
另一態樣關於用作為抗體外寄生蟲劑(尤其是殺節肢動物劑,非常特別是殺蟲劑或殺蟎劑)之式(I)化合物。
本發明之其他態樣為獸醫配製物,其包含有效量的至少一種式(I)化合物及下列中之至少一者:醫藥上可接受之賦形劑(例如固態或液態稀釋劑)、醫藥上可接受之助劑(例如界面活性劑),尤其是習用於獸醫配製物中的醫藥上可接受之賦形劑及/或習用於獸醫配製物中的醫藥上可接受之助劑。
本發明相關的態樣為一種製造如本文所述之獸醫配製物之方法,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/或助劑(尤其是與習用於獸醫配製物中的醫藥上可接受之賦形劑及/或習用於獸醫配製物中的助劑)混合的步驟。
本發明之另一特定態樣為選自根據所述之態樣的殺體外寄生蟲及殺體內寄生蟲配製物之群組的獸醫配製物,尤其是選自驅蟲、抗原蟲及殺節肢動物配製物之群組,非常特別地選自殺線蟲、殺扇形動物、殺棘頭動物、殺舌形動物、殺昆蟲及殺蟎配製物之群組,以及彼等的製備方法。
另一態樣關於一種治療寄生蟲感染(尤其是由選自本文所述之體外 寄生蟲及體內寄生蟲之群組的寄生蟲所引起的感染)之方法,該方法係藉由將有效量的式(I)化合物施用至對其有需要的動物,特別是非人類動物。
另一態樣關於一種治療寄生蟲感染(尤其是由選自本文所述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)之方法,該方法係藉由將如本文所定義之獸醫配製物使用於對其有需要的動物,特別是非人類動物。
另一態樣關於式(I)化合物治療在動物(特別是非人類動物)中的寄生蟲感染(尤其是由選自本文所述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)之用途。
在動物健康或獸醫的倩況下,術語"治療"包括預防性、補救預防性或治療性治療。
在一特定實施態樣中,以此方式,提供用於獸醫領域的至少一種式(I)化合物與其他活性成分(尤其是與殺體內及殺體外寄生蟲劑)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)不同的活性成分調配成共同的配製物且對應地一起施用,且亦關於包含各活性成分的單獨配製物之產品。因此,當欲施用兩種以上的活性成分時,可將所有的活性成分調配成共同的配製物或可將所有的活性成分調配成單獨配製物;同樣地可行的是混合形式,其中將一些活性成分調配在一起及將一些活性成分單獨調配。單獨配製物允許單獨或連續施用討論中的活性成分。
在本文中以彼等的俗名指定之活性成分為已知且描述於(例如)“除害劑手冊(Pesticide Manual)(見上)中或可在網際網路上搜尋(例如http://www.alanwood.net/pesticides)。
來自作為混合組分的殺體外寄生蟲劑之群組的例示性活性成分包括(沒有此將構成限制的任何意圖)在上文詳細列示之殺蟲劑及殺蟎劑。其他可用的活性成分係依照上述根據現行作用分類方案之IRAC模式(IRAC Mode of Action Classification Scheme)的分類列示於下:(1)乙醯膽鹼酯酶(AChE)抑制劑;(2)GABA-閘控之氯離子通道阻斷劑;(3)鈉 通道調節劑;(4)菸鹼乙醯膽鹼受體(nAChR)競爭調節劑;(5)菸鹼乙醯膽鹼受體(nAChR)別位調節劑;(6)麩胺酸閘控之氯離子通道(GluCl)別位調節劑;(7)保幼激素模擬物;(8)雜項非特異性(多位置)抑制劑;(9)弦音器(chordotonal organ)調節劑;(10)蟎生長抑制劑;(12)粒腺體ATP合成酶之抑制劑,諸如ATP干擾劑;(13)經由質子梯度干擾之氧化性磷酸化去偶合劑;(14)菸鹼乙醯膽鹼受體通道阻斷劑;(15)甲殼素生物合成之抑制劑,第0型;(16)甲殼素生物合成抑制劑,第1型;(17)蛻皮干擾劑(尤其在雙翅目中);(18)蛻皮激素受體促效劑;(19)章魚胺能受體促效劑;(21)粒腺體複合物I電子傳遞抑制劑;(25)粒腺體複合物II電子傳遞抑制劑;(20)粒腺體複合物III電子傳遞抑制劑;(22)電壓依賴性鈉通道阻斷劑;(23)乙醯基CoA羧酶之抑制劑;(28)藍尼定(ryanodine)受體調節劑;具有未知或非特異性作用機制之活性成分,例如氟硝二苯胺(fentrifanil)、芬諾靈(fenoxacrim)、環普靈(cycloprene)、克氯苯(chlorobenzilate)、殺蟲脒(chlordimeform)、氟苯滅(flubenzimine)、地昔尼爾(dicyclanil)、磺胺蟎酯(amidoflumet)、蟎離丹(quinomethionate)、苯蟎噻(triarathene)、氯噻唑苯(clothiazoben)、殺蟎好(tetrasul)、油酸鉀、石油、惡蟲酮(metoxadiazone)、紅鈴蟲性誘素(gossyplure)、氟蟎嗪(flutenzine)、新殺蟎(bromopropylate)、冰晶石(cryolite);來自其他類別之化合物,例如畜蟲威(butacarb)、敵蠅威(dimetilan)、除線威(cloethocarb)、磷蟲威(phosphocarb)、亞特松(pirimiphos)(-乙基)、巴拉松(parathion)(-乙基)、滅克松(methacrifos)、o-水楊酸異丙酯、三氯松(trichlorfon)、硫丙磷(sulprofos)、加護松(propaphos)、硫線磷(sebufos)、必達松(pyridathion)、發硫磷(prothoate)、除線磷(dichlofenthion)、滅賜松碸(demeton-S-methyl sulfone)、依殺松(isazofos)、苯腈磷(cyanofenphos)、得拉松(dialifos)、三硫磷(carbophenothion)、奧他硫松(autathiofos)、阿隆芬文松(aromfenvinfos)(-甲基)、谷速松(azinphos)(-乙基)、陶斯松(chlorpyrifos)(-乙基)、丁苯硫磷(fosmethilan)、碘硫磷(iodofenphos)、蔬果磷(dioxabenzofos)、福木松(formothion)、大福松(fonofos)、福拉松(flupyrazofos)、繁福松(fensulfothion)、益多松 (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,例如乙醯蟲腈(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)、阿佛拉那(afoxolaner)、羅提蘭(lotilaner)、氟拉蘭(fluralaner);擬除蟲菊酯類(pyrethroids)(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(protrifenbute)、必滅寧(pyresmethrin)、RU15525、環戊烯丙菊酯(terallethrin)、順式-列滅寧(cis-resmethrin)、右旋七氟甲醚菊酯(heptafluthrin)、百索美寧(bioethanomethrin)、百普美寧(biopermethrin)、芬比寧(fenpyrithrin)、順式-賽滅寧(cis-cypermethrin)、順式-百滅寧(permethrin)、氯氟氰菊(clocythrin)、賽洛寧(cyhalothrin)(λ-)、二氯炔戊菊酯(chlovaporthrin)或鹵化烴化合物(HCH);新菸鹼類(neonicotinoid)(例如硝蟲噻嗪(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)、拉替菌素(latidectin)、莫西菌素(moxidectin)、塞拉菌素(selamectin)、依普菌素(eprinomectin)、多拉菌素(doramectin)、因滅汀(emamectin)苯甲酸鹽;米貝黴素(milbemycin)肟、烯蟲硫酯(triprene)、保幼醚(epofenonane)、二苯丙醚(diofenolan);生物製劑、荷爾蒙或費洛蒙,例如天然產物,例如蘇力菌素(thuringiensin)、十二碳二烯醇(codlemone)或印度苦楝組分;二硝基苯酚,例如白粉克(dinocap)、大脫蟎(dinobuton)、百蟎克(binapacryl);苯甲醯脲,例如氟佐隆(fluazuron)、氟幼脲(penfluron);脒衍生物,例如氯甲丁奉(chlormebuform)、賽咪唑(cymiazole)、得米地曲(demiditraz);蜂箱蜂瓦蟎殺蟎劑,例如有機酸類,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成分包括但不限於活性驅蟲成分及活性抗原蟲成分。
活性驅蟲成分包括但不限於下列的活性殺線蟲、殺白蟻及/或殺絛蟲化合物:來自巨環內酯的類別,例如:依普菌素(eprinomectin)、阿巴汀(abamectin)、奈馬克丁(nemadectin)、莫西菌素(moxidectin)、多拉菌素(doramectin)、塞拉菌素(selamectin)、雷皮菌素(lepimectin)、拉替菌素(latidectin)、密滅汀(milbemectin)、伊維菌素(ivermectin)、因滅汀(emamectin)、米貝黴素(milbemycin);來自苯并咪唑和前苯并咪唑的類別,例如:奧苯達唑(oxibendazole)、甲苯達唑(mebendazole)、三氯苯達唑(triclabendazole)、多保淨(thiophanate)、帕苯達唑(parbendazole)、奧芬達唑(oxfendazole)、奈托比胺(netobimin)、芬苯達唑(fenbendazole)、非班太爾(febantel)、腐絕(thiabendazole)、環苯達唑(cyclobendazole)、坎苯達唑(cambendazole)、阿苯達唑(albendazole)亞碸、阿苯達唑、氟苯達唑(flubendazole);來自酯肽(depsipeptide)的類別,較佳環酯肽,特別是24-員環酯肽,例如:艾默德斯(emodepside)、PF1022A;來自四氫嘧啶的類別,例如:莫侖太爾(morantel)、噻嘧啶(pyrantel)、奧克太爾(oxantel);來自咪唑并噻唑的類別,例如:布他咪唑(butamisole)、左旋咪唑(levamisole)、四咪唑(tetramisole);來自胺苯基脒的類別,例如:阿米太爾(amidantel)、去醯基化阿米太爾(dAMD)、三苯雙脒(tribendimidine);來自胺基乙腈的類別,例如:莫盤太爾(monepantel);來自對郝青醯胺(paraherquamide)的類別,例如:對郝青醯胺、得曲恩特(derquantel);來自柳醯胺苯的類別,例如:三溴沙侖(tribromsalan)、溴沙尼特(bromoxanide)、溴替尼特(brotianide)、氯碘沙尼(clioxanide)、氯氰碘柳胺(closantel)、氯硝柳胺(niclosamide)、羥氯柳苯胺(oxyclozanide)、雷複尼特(rafoxanide); 來自經取代之酚的類別,例如:硝碘酚腈(nitroxynil)、硫雙二氯酚(bithionole)、二碘硝酚(disophenol)、六氯酚(hexachlorophen)、聯硝氯酚(niclofolan)、美克芬崙(meniclopholan);來自有機磷酸酯的類別,例如:三氯松(trichlorfon)、萘肽磷(naftalofos)、二氯松(dichlorvos)/DDVP、育畜磷(crufomate)、牛壁逃(coumaphos)、哈洛克酮(haloxon);來自哌酮/喹啉的類別,例如:吡喹酮(praziquantel)、依西太爾(epsiprantel);來自哌的類別,例如:哌、羥嗪(hydroxyzine);來自四環黴素的類別,例如:四環素、氯四環素、去氧羥四環素(doxycycline)、氧四環素(oxytetracycline)、吡甲四環素(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(lucanthone)、海恩酮(hycanthon)、海托啉(hetolin)、吐根素(emetine)、乙胺嗪(diethylcarbamazine)、二氯芬(dichlorophen)、地芬尼泰(diamfenetid)、氯硝西泮(clonazepam)、苄芬寧(bephenium)、硝硫氰胺(amoscanate)、氯舒隆(clorsulon)。
活性抗原蟲成分包括但不限於下列活性成分:來自三的類別,例如:地克朱利(diclazuril)、波那朱利(ponazuril)、勒崔朱利(letrazuril)、托曲朱利(toltrazuril);來自聚醚離子載體的類別,例如:莫能黴素(monensin)、鹽黴素(salinomycin)、馬杜黴素(maduramicin)、甲基鹽黴素(narasin);來自巨環內酯的類別,例如:米貝黴素(milbemycin)、紅黴素(erythromycin);來自喹諾酮的類別,例如:恩諾沙星(enrofloxacin)、普多沙星(pradofloxacin);來自奎寧的類別,例如:氯奎寧(chloroquin);來自嘧啶的類別,例如:乙胺嘧啶(pyrimethamine); 來自磺醯胺的類別,例如:磺胺喹啉(sulfaquinoxaline)、甲氧苄啶(trimethoprim)、磺胺氯吡(sulfaclozin);來自硫胺的類別,例如:氨丙啉(amprolium);來自林可醯胺(lincosamines)的類別,例如:克林達黴素(clindamycin);來自羰胺苯的類別,例如:雙咪苯脲(imidocarb);來自硝基呋喃的類別,例如:硝呋替莫(nifurtimox);來自喹唑啉酮生物鹼的類別,例如:鹵夫酮(halofuginone);來自各種其他類別,例如:奧沙尼喹(oxamniquin)、巴龍黴素(paromomycin);來自微生物之疫苗或抗原的類別,例如:來自疫苗類別或來自微生物之抗原,例如:羅氏犬焦蟲(Babesia canis rossi)、盲腸型球蟲(Eimeria tenella)、早熟艾美球蟲(Eimeria praecox)、毒害艾美球蟲(Eimeria necatrix)、緩艾美球蟲(Eimeria mitis)、巨型艾美球蟲(Eimeria maxima)、布氏艾美球蟲(Eimeria brunetti)、堆形艾美球蟲(Eimeria acervulina)、佛氏犬焦蟲(Babesia canis vogeli)、嬰兒利什曼原蟲(Leishmania infantum)、犬焦蟲症(Babesia canis canis)、牛肺蟲(Dictyocaulus viviparus)。
所有述及之混合組分,若根據彼等的官能基能夠的話,則可視情況亦可與適當鹼或酸形成鹽。
式(I)化合物亦可用於病媒控制。在本發明的情況下,病媒為能夠將病原體(例如病毒、蠕蟲、單細胞生物與細菌)從儲體(植物、動物、人類、等等)傳播至宿主之節肢動物,特別是昆蟲或蜘蛛。該等病原體可經由機械式(例如經由非叮咬性蠅傳播之沙眼)傳播在宿主上或注射後傳播至宿主(例如經由蚊子之瘧疾寄生蟲)中。
病媒及彼等所傳播之疾病或病原體的實例為:1)蚊子- 瘧蚊(Anopheles):瘧疾(malaria)、絲蟲病(filariasis);- 家蚊(Culex):日本腦炎、絲蟲病、其他病毒疾病、其他蠕蟲之傳播;- 斑蚊(Aedes):黃熱病、登革熱、其他病毒性疾病、絲蟲病; - 蚋科(Simuliidae):蠕蟲(特別是蟠尾絲蟲(Onchocerca volvulus))之傳播;- 蛾蚋科(Psychodidae):利什曼體病(leishmamiasis)的傳播2)蝨:皮膚傳染病、流行性斑疹傷寒;3)蚤:鼠疫、地方性斑疹傷寒、絛蟲;4)蠅:昏睡症(錐蟲病);霍亂、其他細菌性疾病;5)蟎:蟎病(acariosis)、流行性斑疹傷寒、痘立克次體、兔熱病、聖路易斯腦炎(Saint Louis encephalitis)、蜱傳腦炎(TBE)、克里米亞-剛果出血熱、回歸熱;6)蜱:疏螺旋體病(borelliosis)諸如伯氏疏螺旋體(Borrelia burgdorferi sensu lato)、杜通氏螺旋體(Borrelia duttoni)、蜱傳性腦炎、Q熱(貝氏考克斯菌(Coxiella bumetii))、焦蟲症(犬焦蟲症(Babesia canis canis))、艾利希氏體症(ehrlichiosis)。
在本發明的情況下病媒之實例為可將植物病毒傳播至植物之昆蟲,例如:蚜蟲、蠅、葉蟬或薊馬。其他能夠傳播植物病毒之病媒為蜘蛛蟎、蝨、甲蟲和線蟲。
在本發明的情況下病媒之另外實例為可將原菌傳播病至動物與/或人類之昆蟲與蜘蛛諸如蚊子,尤其是斑蚊(Aedes)、瘧蚊(Anopheles),例如,甘比亞瘧蚊(A.gambiae)、阿拉伯瘧蚊(A.arabiensis)、致死瘧蚊(A.funestus)、大劣瘧蚊(A.dirus)(瘧疾)與家蚊(Culex)、蝨、跳蚤、蠅、蟎、和蜱。
若式(I)化合物係突破抗性,則亦可能控制病媒。
就本發明的意義而言之病媒的其他實例為能夠將病原體傳播至動物及/或人類的昆蟲和蜘蛛諸如蚊子,特別是斑蚊(Aedes)、瘧蚊(Anopheles)(例如甘比亞瘧蚊(A.gambiae)、阿拉伯瘧蚊(A.arabiensis)、致死瘧蚊(A.funestus)、大劣瘧蚊(A.dirus)(瘧疾)與家蚊(Culex)、蛾蚋科諸如白蛉屬(Phlebotomus)、羅蛉屬(Lutzomyia)、蝨、跳蚤、蒼蠅、蟎和壁蝨。
若式(I)化合物具有抗性破壞,則亦可能控制病媒。
式(I)化合物適合用於預防由病媒傳播的疾病及/或病原體。因此, 本發明之另一態樣為式(I)化合物用於病媒控制之用途,例如用於農業、園藝、森林、花園和休閒設施,及亦於保護材料和儲存產物。
式(I)化合物適合於防止工業材料受到昆蟲(例如來自鞘翅目(Coleoptera)、膜翅目(Hymenoptera)、等翅目(Isoptera)、鱗翅類(Lepidoptera)、嚙蟲目(Psocoptera)和衣魚目(Zygentoma))的攻擊或破壞。
工業材料在本文中係理解為意指無生命材料,諸如較佳為塑膠、黏著劑、膠水、紙張及紙板、皮革、木材、加工木製品及塗料組成物。本發明使用於保護木材是特佳的。
在另一實施態樣中,式(I)化合物係與至少一種其他的殺蟲劑及/或至少一種殺真菌劑一起使用。
在另一實施態樣中,式(I)化合物係以備用除害劑存在,意指彼等可不進一步修飾而施用至討論中的材料。有用的其他殺蟲劑或殺真菌劑尤其包括彼等上文所述及者。
令人驚訝地,亦發現式(I)化合物可用於防止與鹽水或半鹹水進行接觸之物體(特別是船體、隔板、編網、建築物、繫泊和傳訊系統)被污塞。同樣地可能使用單獨或與其他活性化合物組合的式(I)化合物作為抗污塞劑。
式(I)化合物適合於控制衛生領域中的動物害蟲。更具體地說,本發明可用於居家保護領域、衛生保護領域及保護儲存產品,特別用於控制在封閉空間(例如公寓、廠房、辦公室、車廂、動物繁殖場)中所遇到的昆蟲、蜘蛛、蜱和蟎。為了控制動物害蟲,式(I)化合物係單獨或與其他活性成分及/或助劑組合使用。彼等較佳地用於居家殺蟲劑產品中。式(I)化合物有效對抗敏感性及抗性物種,且對抗所有發育期。
此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。
施用係以例如下列方式進行:氣霧劑、不加壓噴灑產品(例如泵壓及霧化噴灑器)、自動噴霧系統、噴霧器、發泡體、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,呈顆粒或細粉,用於散佈之誘餌或誘餌台。
製備例:
7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒
的合成:
最初將在無水甲苯(1300ml)中的4-溴-N-甲基-6-(五氟乙基)嗒-3-胺(46g,0.15mol)裝入配備磁力攪拌棒和隔膜的乾燥氬氣填充之燒瓶。接著添加1,1-二苯基甲亞胺(34g,0.19mol)、三級丁醇鈉(20.2g,0.21mol)及[1,1’-雙(二苯膦基)二茂鐵]二氯鈀(II),與二氯甲烷複合(5.5g,7.5mmol)。添加各試劑後,進行脫氣操作。將混合物在90℃下攪拌66h且接著在105℃下攪拌30h。在105℃下2小時後進一步添加試劑,第一種包含1,1-二苯基甲亞胺(9g,0.05mol)、三級丁醇鈉(5g,0.053mol)及[1,1’-雙(二苯膦基)二茂鐵]二氯鈀(II),與二氯甲烷複合(1.5g,2mmol)及第二種包含1,1-二苯基甲亞胺(5.1g,28mmol)、三級丁醇鈉(3g,31mmol)及[1,1’-雙(二苯膦基)二茂鐵]二氯-鈀(II),與二氯甲烷複合(0.8g,1.1mmol)。添加各試劑後,進行脫氣操作。接著將反應混合物在105℃下攪拌另15h且然後濃縮。接著添加水(500ml)和濃鹽酸(500ml)並將混合物在回流下攪拌另6小時,並添加濃乙酸乙酯(500ml)和水(300ml)及分離各相。用10%鹽酸(2 x 50ml)萃取有機相。用乙酸乙酯洗滌水相 並在0℃下用固體形式的碳酸鈉中和。將粗產物用乙酸乙酯(3 x 100ml)萃取及用無水硫酸鈉乾燥。過濾後,在減壓下移除溶劑並藉由溶解在原甲酸三乙酯(300ml)中萃取殘餘物。將混合物在120℃下攪拌1.5h並濃縮。藉由層析法純化粗產物,其產生呈黃色固體的7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒(10g,26%)。
5-氟-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒
-6-基]-吡啶-2-甲酸甲酯的合成:
在氬氣下於25℃將TMPZnCl.LiCl(在THF中的1.31M,1.67ml,2.18mmol)加至溶解在(4ml)中的7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒(500mg,1.98mmol);將此反應溶液攪拌10min。接著,在25℃下添加在THF(4ml)中的5-氟-6-碘吡啶-2-甲酸甲酯(1.12g,3.96mmol)及肆(三苯膦)鈀(0)(230mg,0.19mmol)並將溶液在80℃下繼續攪拌3小時。在藉由添加飽和氯化銨溶液之標準後處理之後,用乙酸乙酯萃取反應混合物,用Na2SO4乾燥合併的有機相並在膜泵真空下濃縮。在藉由管柱層析法(乙酸乙酯/環己烷)純化之後,獲得於白色固體形式的5-氟-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒-6-基]吡啶-2-甲酸甲酯(310mg,39%)。
MH+:406.1;1H NMR(d6-DMSO):8.83(s,1H),8.43(dd,1H),8.28(t,1H),4.32(s,3H),3.96(s,3H)。
6-(6-溴-3-氟吡啶-2-基)-7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]-嗒
的合成:
在氬氣下於25℃將TMPZnCl.LiCl(在THF中的1.31M,2.67ml,3.49mmol)加至溶解在(4ml)中的7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒(800mg,3.17mmol);將此反應溶液攪拌10min。接著,在25℃下添加在THF(4ml)中的6-溴-3-氟-2-碘吡啶(1.916g,6.34mmol)及肆(三苯膦)鈀(0)(367mg,0.31mmol)並將溶液在80℃下繼續攪拌4小時。在藉由添加飽和氯化銨溶液之標準後處理之後,用乙酸乙酯萃取反應混合物,用Na2SO4乾燥合併的有機相並在膜泵真空下濃縮。在藉由管柱層析法(乙酸乙酯/環己烷)純化之後,獲得於白色固體形式的6-(6-溴-3-氟吡啶-2-基)-7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒(617mg,46%)。
MH+:427.9;1H NMR(d6-DMSO):δ 8.81(s,1H),8.11(m,2H),4.25(s,3H)。
5-(乙硫基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]-嗒
-6-基]吡啶-2-甲酸甲酯的合成:
最初將在無水THF(4毫升)中的5-氟-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒-6-基]吡啶-2-甲酸甲酯(150mg,0.37mmol)裝入配備磁攪拌棒及隔膜的乾燥氬氣填充之Schlenk燒瓶中。在-20℃下添加氫化鈉(15.1mg,0.37mmol),且將溶解在4毫升THF中的乙硫醇(26mg,0.40mmol)在-20℃至最高-10℃下滴加至其中。將混合物在20℃下攪拌1.5h。將飽和氯化銨水溶液(25ml)加至反應混合物中,將其以乙酸乙酯(3 x 50 毫升)萃取並用無水硫酸鈉乾燥。過濾後,在減壓下移除溶劑。藉由層析法純化粗產物,其產生於白色固體形式的5-(乙硫基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒-6-基]吡啶-2-甲酸甲酯(104mg,63%)。
MH+:448.1;1H NMR(400MHz,d6-DMSO)δ ppm:8.80(s,1H),8.24(d,1H),8.21(d,1H),4.23(s,3H),3.93(s,3H),3.13(q,2H),1.29(t,3H)。
5-(乙磺醯基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]-嗒
-6-基]吡啶-2-甲酸甲酯的合成:
最初將在二氯甲烷(2ml)中的5-(乙硫基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒-6-基]-吡啶-2-甲酸甲酯(781mg,1.74mmol)裝入配備磁攪拌棒及隔膜的乾燥氬氣填充之Schlenk燒瓶中。在20℃下依次添加甲酸(402mg,8.72mmol)和過氧化氫(35%;1.19g,12.2mmol)。將混合物在20℃下攪拌4h。在0℃下將亞硫酸氫鈉、碳酸氫鈉和飽和氯化銨水溶液加至反應混合物中,將其以二氯甲烷萃取並用無水硫酸鈉乾燥。過濾後,在減壓下移除溶劑。藉由層析法純化粗產物,其產生於白色固體形式的5-(乙磺醯基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒-6-基]吡啶-2-甲酸甲酯(603mg,73%)。
MH+:480.1;1H NMR(400MHz,d6-DMSO)δ ppm:8.85(s,1H),8.79(d,1H),8.58(d,1H),3.98(s,3H),3.97(s,3H),3.78(q,2H),1.21(t,3H)。
N-乙基-5-(乙磺醯基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]-嗒
-6-基]吡啶-2-甲醯胺的合成:
最初將在甲醇(2ml)中的5-(乙磺醯基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒-6-基]-吡啶-2-甲酸甲酯(100mg,0.20mmol)裝入配備磁攪拌棒及隔膜的乾燥氬氣填充之Schlenk燒瓶中。在20℃下添加乙胺(94.1mg,2.08mmol)並將混合物在20℃下攪拌1h。將飽和氯化銨水溶液(25ml)加至反應混合物中,將其以乙酸乙酯(3 x 50ml)萃取及用無水硫酸鈉乾燥。過濾後,在減壓下移除溶劑。藉由層析法純化粗產物,其產生於白色固體形式的N-乙基-5-(乙磺醯基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒-6-基]吡啶-2-甲醯胺(65mg,63%)。
MH+:493.1;1H NMR(400MHz,d6-DMSO)δ ppm:9.04(t,1H),8.87(s,1H),8.75(d,1H),8.53(d,1H),4.01(s,3H),3.79(q,2H),3.34(q,2H),1.21(t,3H),1.12(t,3H)。
1-{5-(乙磺醯基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒
-6-基]吡啶-2-基}-3-甲基脲的合成:
最初將在無水二烷(2ml)中的6-[6-溴-3-(乙磺醯基)吡啶-2-基]-7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]-嗒(100mg,0.20mmol)裝入配備有磁攪拌棒及隔膜的乾燥氬氣填充之Schlenk燒瓶中。接著添加甲脲(18mg,0.24mmol)、碳酸銫(98mg,0.30mmol)、9,9-二甲基-4,5-雙(二苯膦基)二苯并哌喃(12mg,0.02mmol)及雙(二亞苯甲基丙酮)鈀(0)(6mg,0.02mmol),且將混合物在80℃下攪拌1h。將飽和氯化鈉水溶液(25ml) 加至反應混合物中,將其以乙酸乙酯(3 x 50ml)萃取並用無水硫酸鈉乾燥。過濾後,在減壓下移除溶劑。藉由層析法純化粗產物,其產生於白色固體形式的1-{5-(乙磺醯基)-6-[7-甲基-3-(五氟乙基)-7H-咪唑并[4,5-c]嗒-6-基]吡啶-2-基}-3-甲基脲(82mg,83%)。
MH+:494.0;1H NMR(400MHz,d6-DMSO)δ ppm:10.13(s,1H),8.81(s,1H),8.37(d,1H),8.07(d,1H),7.13(bs,1H),3.94(s,3H),3.59(q,2H),2.71(d,3H),1.18(t,3H)。
化合物係根據EEC Directive 79/831 Annex V.A8在反相管柱(C 18)上以HPLC(高效液相層析法)分離。溫度:55℃。
在酸性範圍內的M+之LC-MS測定係在pH 2.7下以0.1%水性甲酸及乙腈(含有0.1%甲酸)作為溶析劑進行;線性梯度係從10%乙腈至95%乙腈;儀器:Agilent 1100 LC-系統、Agilent MSD系統、HTS PAL。
在中性範圍內的M+之LC-MS測定係在pH 7.8下以0.001莫耳碳酸氫銨水溶液及乙腈作為溶析劑進行;線性梯度係從10%乙腈至95%乙腈。
所選實施例的NMR數據係以習知的形式(δ值,多重分裂,氫原子數目)或以NMR峰列表形式列示。
在各情況不,陳述其中記錄NMR光譜之溶劑。
類似於實施例及藉由上述之製備方法可能獲得表1中所列示之式(I)化合物:
所選實施例的NMR數據:
NMR峰列表方法
所選實施例之1H NMR數據係以1H NMR-峰列表之形式指明。對於各訊號峰,首先列出δ值(ppm)及接著在圓括弧中的訊號強度。不同訊號峰的δ值-訊號強度值對以分號彼此分開列示。
一實施例之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)
在列印的NMR光譜(以cm表示)之實例中尖銳訊號的強度係與訊號之高度有關且顯示訊號強度的真正比率。在寬訊號的情況下,可顯示數個峰或訊號的半高(middle)及彼等相較於光譜中最強訊號的相對強度。
為了校正1H光譜的化學位移,吾人使用四甲矽烷及/或溶劑的化學位移,特別是在光譜於DMSO中測量的情形下。因此在NMR峰列表中,可能但不一定會出現四甲矽烷的峰。
1H-NMR峰列表係類似於習知1H-NMR列印且因此通常包含所有在習知NMR判讀中所列示的峰。
另外,如同習知的1H NMR印表,彼等可顯示溶劑訊號、標的化合物之立體異構物(其同樣構成本發明目標的一部分)及/或雜質峰的訊號。
在溶劑及/或水之δ範圍內的化合物訊號之報告中,吾等的1H NMR峰列表顯一般溶劑峰(例如在d6-DMSO中之DMSO的峰)及水的峰,其通 常平均具有高強度。
標的化合物之立體異構物的峰及/或雜質的峰通常平均具有比標的化合物(例如具有>90%的純度)更低的強度。
該等立體異構物及/或雜質可為特定製備方法之典型。彼等之峰因此可參考“副產物指紋”而幫助識別吾等之製備方法的再現性。
以已知的方法(MestreC、ACD模擬,但亦以憑經驗評估之期望值)計算標的化合物之峰的專家若必要時可視情況使用附加的強度濾波器分離出標的化合物之峰。此分離可能類似於在習知1H NMR判讀之相關峰挑選。
可在Research Disclosure Database Number 564025中發現1H NMR峰列表的更多細節。
貓櫛頭蚤(Ctenocephalides felis)-與成年貓蚤的體外接觸試驗
為了試管之塗覆,先將9mg的活性成分溶於1ml的丙酮p.a.中及接著以丙酮p.a.稀釋至所欲濃度。藉由在軌道式振盪器上翻轉及搖動(以30rpm搖動旋轉2h)將250μl的溶液均勻分布在25ml玻璃試管內壁及底部。使用900ppm活性成分溶液及內表面積44.7cm2,產生均勻分布,達到5μg/cm2之以面積為基準的劑量。
溶劑蒸發後,將5-10隻貓蚤(貓櫛頭蚤)成蟲移居此等試管,以多孔塑料蓋密封並室溫下及周圍濕度下以水平位置培育。48h之後,測定效力。為此,試管為直立的並將貓蚤敲擊至試管底部。在底部維持不動或以不協調方式移動的貓蚤係視為死亡或瀕死。
若在此試驗中以5μg/cm2的施用率達到至少80%效力,則物質顯示對抗貓櫛頭蚤之良好效力。100%效力意指所有的貓蚤死亡或瀕死。0%效力意指無貓蚤受到傷害。
在此試驗中,例如,下列來自製備例之化合物於5μg/cm2(=500g/ha)的施用率下顯示100%之效力:I-09、I-10、I-11、I-12、I-13
貓櫛頭蚤(Ctenocephalides felis)-口服試驗
溶劑:二甲亞碸
為了製造適當的活性成分配製物,將10mg的活性成分與0.5ml的二甲亞碸混合。以檸檬酸化的牛血稀釋產生所欲濃度。
將約20隻未餵食的貓蚤(貓櫛頭蚤)成蟲放入一頂部和底部以紗布封閉的室中。將底端用封口膜(parafilm)封閉的金屬圓筒放置在室上。此圓筒含有血/活性成分配製物,貓蚤可通過封口膜吸食該血/活性成分配製物。
2天後,測定殺死%。100%意指所有的貓蚤已被殺死;0%意指無任何貓蚤被殺死。
在此試驗中,例如,下列來自製備例的化合物於100ppm的施用率下顯示100%的效力:I-08、I-09、I-10、I-11、I-12、I-13
銅綠蠅(Lucilia cuprina)試驗
溶劑:二甲亞碸
為了製造適合的活性成分配製物、將10mg的活性成分與0.5ml的二甲亞碸混合,且將濃縮物以水稀釋至所欲濃度。
將約20隻澳洲綿羊綠頭蒼蠅(銅綠蠅)L1齡幼蟲轉移至含有碎馬肉及所欲濃度的活性成分配製物之試驗容器中。
在2天後,測定殺死%。100%意指所有的幼蟲已被殺死;0%意指沒有幼蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物於100ppm的施用率下顯示100%之效力:I-01、I-02、I-03、I-04、I-05、I-08、I-09、I-10、I-11、I-12、I-13
在此試驗中,例如,下列來自製備例之化合物於100ppm的施用率下顯示95%之效力:I-06
在此試驗中,例如,下列來自製備例之化合物於100ppm的施用率下顯示90%之效力:I-14
家蠅(Musca domestica)試驗
溶劑:二甲亞碸
為了製造適當的活性成分配製物,將10mg的活性成分與0.5ml的二甲亞碸混合,且將濃縮物以水稀釋至所欲濃度。
將10隻家蠅(houseflies)(家蠅(Musca domestica))成蟲移居至含有用糖溶液和所欲濃度之活性成分配製物處理的海綿之容器中。
2天後,測定殺死%。100%係指所有的蒼蠅已被殺死;0%係指沒 有任何蒼蠅被殺死。
在此試驗中,例如,下列來自製備例之化合物於100ppm的施用率下顯示100%之效力:I-01
在此試驗中,例如,下列來自製備例之化合物於100ppm的施用率下顯示90%之效力:I-10
在此試驗中,例如,下列來自製備例之化合物於100ppm的施用率下顯示80%之效力:I-04、I-13
南方根瘤線蟲(Meloidogyne incognita)試驗
溶劑:125.0重量份丙酮
為了製造活性成分的適當配製物,將1重量份活性成分與所述量之溶劑混合且將濃縮物以水稀釋至所欲濃度。
將容器裝滿沙子、活性成分溶液、南方根瘤線蟲(southem root-knot nematode)(南方根瘤線蟲(Meloidogyne incognita))之卵/幼蟲懸浮液及萵苣種子。萵苣種子發芽且植物發育。根上發育出癭瘤。
在14天後,以癭瘤的形成測定殺線蟲效力%。100%意指未發現癭瘤;0%意指在經處理之植物上的癭瘤數量相當於未經處理之對照組。
在此試驗中,例如,下列來自製備例之化合物於20ppm的施用率下顯示100%之效力:I-08、I-09、I-10、I-12、I-13
在此試驗中,例如,下列來自製備例之化合物於20ppm的施用率下顯示90%之效力I:I-01、I-02、I-15
桃蚜(Myzus persicae)-口服試驗
溶劑:100重量份丙酮
為了製造適合的活性成分配製物,將1重量份活性成分以所述重量份之溶劑溶解且以水補充至所欲濃度。
將50μl的活性成分製劑轉移至微滴定盤中且以150μl的IPL41昆蟲培養基(33%+15%糖)補充至200μl最終體積。隨後,用封口膜(parafilm)密封該盤,第二微滴定盤內的綠桃蚜(green peach aphid)(桃蚜(Myzus persicae))之混合群體能夠將其刺穿且吸入溶液。
在5天後,測定效力%。100%意指所有的蚜蟲已被殺死;0%意指沒有蚜蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物於0.8ppm的施用率下顯示100%之效力:I-01、I-02、I-03、I-04、I-05、I-06、I-10、I-11、I-12、I-13、I-15,
在此試驗中,例如,下列來自製備例之化合物於0.8ppm的施用率下顯示90%之效力:I-07、I-08、I-09、I-14
桃蚜-噴灑試驗
溶劑:78重量份丙酮1.5重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解且以含有1000ppm乳化劑濃度的水補充至所欲濃度。為了製造更多的試驗濃度,將配製物以含有乳化劑的水稀釋。
將受到所有階段的綠桃蚜(桃蚜)侵襲的大白菜(Chinese cabbage)葉(山東白菜(Brassica pekinensis))圓盤以所欲濃度之活性成分配製物噴灑。
在5天後測定效力%。100%意指所有的蚜蟲已被殺死;0%意指沒有蚜蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物於100g/ha的施用率下顯示100%之效力:I-02、I-03、I-04、I-15
在此試驗中,例如,下列來自製備例之化合物於100g/ha的施用率下顯示90%之效力:I-01、I-05、I-06、I-08、I-12
在此試驗中,例如,下列來自製備例之化合物於20g/ha:的施用率下顯示100%之效力:I-08、I-09、I-10
在此試驗中,例如,下列來自製備例之化合物於20g/ha的施用率下顯示90%之效力:I-03、I-05、I-12、I-13、I-15
辣根猿葉甲(Phaedon cochleariae)-噴灑試驗
溶劑:78.0重量份丙酮1.5重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重 量份之溶劑溶解並以含1000ppm的乳化劑濃度之水補充至所欲濃度。為了製造另外的試驗濃度,將配製物以含有乳化劑的水稀釋。
將大白菜(Chinese cabbage)葉(山東白菜(Brassica pekinensis))圓盤以所欲濃度之活性成分配製物噴灑,且乾燥後,移居油菜籽甲蟲(辣根猿葉甲(Phaedon cochleariae))之幼蟲。
在7天之後,測定效力%。100%意指所有的甲蟲幼蟲已被殺死;0%意指沒有甲蟲幼蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物於100g/ha的施用率下顯示100%之效力:I-01、I-02、I-03、I-04、I-05、I-07、I-08、I-09、I-10、I-11、I-12、I-13、I-14、I-15
草地夜蛾(Spodoptera frugiperda)-噴灑試驗
溶劑:78.0重量份丙酮1.5重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解並以含1000ppm的乳化劑濃度之水補充至所欲濃度。為了製造另外的試驗濃度,將配製物以含有乳化劑的水稀釋。
將玉米(玉蜀黍(Zea mays))之葉圓盤以所欲濃度之活性成分配製物噴灑,且乾燥後,移居夜盜蛾(草地夜蛾)之毛蟲。
在6天之後,測定效力%。100%意指所有的毛蟲已被殺死;0%意指沒有毛蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物於100g/ha的施用率下顯示83%之效力:I-13
二點葉蟎(Tetranychus urticae)-噴灑試驗,OP-抗性
溶劑:78.0重量份丙酮1.5重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解並以含1000ppm的乳化劑濃度之水補充至所欲濃度。為了製造另外的試驗濃度,將配製物以含有乳化劑的水稀釋。
將受到所有階段的溫室紅蜘蛛蟎(二點葉蟎)侵襲的豆葉(菜豆(Phaseolus vulgaris))圓盤以所欲濃度之活性成分配製物噴灑。
在6天後測定效力%。100%意指所有的蜘蛛蟎已被殺死;0%意指沒有蜘蛛蟎被殺死。
在此試驗中,例如,下列來自製備例之化合物於4g/ha的施用率下顯示90%之效力:I-08
對比例
辣根猿葉甲(Phaedon cochleariae)-噴灑試驗(PHAECO)
溶劑:78.0重量份丙酮1.5重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解並以含1000ppm的乳化劑濃度之水補充直到達成所欲濃度。為了製造另外的試驗濃度,將混合物以含有乳化劑的水稀釋。
將大白菜葉(山東白菜)圓盤以所欲濃度之活性成分配製物噴灑,且乾燥後,移居油菜籽甲蟲(辣根猿葉甲)之幼蟲。
在所欲時間後,測定效力%。100%意指所有的甲蟲幼蟲已被殺死;0%意指沒有甲蟲幼蟲被殺死。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
桃蚜(Myzus persicae)-噴灑試驗(MYZUPE)
溶劑:78.0重量份丙酮1.5重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以所述重量份的溶劑溶解並以含1000ppm的乳化劑濃度之水補充直到達成所欲濃度。為了製造另外的試驗濃度,將混合物以含有乳化劑的水稀釋。
將將受到所有階段的綠桃蚜(桃蚜)侵襲的大白菜(山東白菜)葉圓盤以所欲濃度之活性成分配製物噴灑。
在所欲時間後,測定效力%。100%意指所有的蚜蟲已被殺死;0% 意指沒有蚜蟲被殺死。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
南方根瘤線蟲(Meloidogyne incognita)試驗(MELGIN)
溶劑:125.0重量份丙酮
為了製造適合的活性成分配製物,將1重量份活性成分與指定量的溶劑混合且將濃縮物以水稀釋至所欲濃度。
將容器裝滿沙子、活性成分溶液、南方根瘤線蟲(southern root-knot nematode)(南方根瘤線蟲(Meloidogyne incognita))之蟲卵/幼蟲懸浮物及萵苣種子。萵苣種子發芽且植物發育。根上發育出根瘤。
在所欲時間後,以根瘤形成%測定殺線蟲效果。100%意指沒有發現根瘤;0%意指在經處理之植物上的根瘤數目相當於未經處理之對照植物上的根瘤數目。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
棉蚜(Aphis gossypii)-噴灑試驗(APHIGO)
溶劑:14重量份二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解並以含有1000ppm乳化劑濃度的水補充直到達成所欲濃度。為了製造另外的試驗濃度,將混合物以含有乳化劑的水稀釋。若需要添加銨鹽或/及滲透劑,則將此等各自以1000ppm濃度加至製備溶液中。
將受到棉蚜(cotton aphid)(棉蚜(Aphis gossypii))嚴重侵襲的棉植物(陸地棉(Gossypium hirsutum))以所欲濃度之活性成分配製物噴灑。
在所欲時間後,測定殺死%。100%意指所有的蚜蟲已被殺死;0%意指沒有蚜蟲被殺死。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
桃蚜(Myzus persic)-噴灑試驗(MYZUPE S)
溶劑:14重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解並以含1000ppm的乳化劑濃度之水補足直到達成所欲濃度。為了製造另外的試驗濃度,將混合物以含有乳化劑的水稀釋。若需要添加銨鹽或/及滲透劑,則將此等各自以1000ppm之濃度加至製備溶液中。
將受到綠桃蚜(桃蚜)嚴重侵襲的甜椒植物(燈籠椒((Capsicum annuum))以所欲濃度之活性成分配製物噴灑處理。
在所欲時間後,測定殺死%。100%意指所有的動物已被殺死;0%意指沒有動物被殺死。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
桃蚜-澆灌試驗(MYZUPE D)
溶劑:7重量份的二甲基甲醯胺
乳化劑:2重量份的烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分與指定量的溶劑及乳化劑混合,且將濃縮物以水稀釋至所欲濃度,有必要考慮進行澆灌的土壤體積。應確保在土壤中不超過40ppm乳化劑濃度。為了製造另外的試驗濃度,將混合物以水稀釋。
將土壤盆中受到所有階段的綠桃蚜(桃蚜)侵襲的皺葉甘藍(Savoy cabbage)植物(甘藍菜(Brassica oleracea))以所欲濃度之活性成分配製物澆灌。
在所欲時間後,測定效力%。100%意指所有的蚜蟲已被殺死;0%意指沒有蚜蟲被殺死。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
辣根猿葉甲(Phaedon cochleariae)-噴灑試驗(PHAECO S)
溶劑:14重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解並以含1000ppm的乳化劑濃度之水補充直到達成所欲濃度。為了製造另外的試驗濃度,將混合物以含有乳化劑的水稀釋。若需要添加銨鹽或/及滲透劑,則將此等各自以1000ppm之濃度加至製備溶液中。
將高麗菜葉(甘藍菜(Brassica oleracea))以所欲濃度之活性成分配製物噴灑且移居油菜籽甲蟲(辣根猿葉甲(Phaedon cochleariae))之幼蟲。
在所欲時間後,測定殺死%。100%意指所有的甲蟲幼蟲已被殺死;0%意指沒有甲蟲幼蟲被殺死。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
黃瓜條葉甲(Diabrotica balteata)-澆灌試驗(DIABBA)
溶劑:7重量份的二甲基甲醯胺
乳化劑:2重量份的烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分與指定量的溶劑及乳化劑混合,且將濃縮物以水稀釋至所欲濃度,有必要考慮進行澆灌的土壤體積。應確保在土壤中不超過40ppm乳化劑濃度。為了製造另外的試驗濃度,將混合物以水稀釋。
在各情況下,將5顆玉米粒播種於裝滿土壤的盆中(玉蜀黍),並於次日以所欲濃度之活性成分配製物澆灌。1天後,加入25隻帶狀黃瓜甲蟲(黃瓜條葉甲)之L2幼蟲。
在8天後,測定效力%。100%意指全部5株植物已經發芽並生長;0%意指沒有植物出現。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
南方根瘤線蟲(Meloidogyne incognita)試驗(MELGIN D)
溶劑:7重量份的二甲基甲醯胺
乳化劑:2.5重量份的烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分與指定量的溶劑及乳化劑混合,且將濃縮物以水稀釋至所欲濃度,有必要考慮 進行澆灌的土壤體積。應確保在土壤中不超過20ppm乳化劑濃度。為了製造另外的試驗濃度,將混合物以水稀釋。
用活性成分溶液澆灌充滿土壤(砂壤土)的盆子。加入南方根瘤線蟲(southern root-knot nematode)(南方根瘤線蟲(Meloidogyne incognita))的卵/幼蟲懸浮液,並將萵苣種子散佈在土壤表面上並用石英砂覆蓋。萵苣種子發芽且幼苗發育。根上發育出根瘤。
在所欲時間後,參照根瘤形成%測定殺線蟲效果。100%意指沒有發現根瘤;0%意指在經處理之植物上的根瘤數目相當於未經處理之對照植物的根瘤數目。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
褐飛蝨(Nilaparvata lugens)-噴灑試驗(NILALU)
溶劑:52.5重量份丙酮7重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解並以含1000ppm的乳化劑濃度之水補足直到達成所欲濃度。為了製造另外的試驗濃度,將混合物以含有乳化劑的水稀釋。若需要添加銨鹽或/及滲透劑,則將此等各自以1000ppm之濃度加至製備溶液中。
將稻米植物(稻(Oryza sativa))以所欲濃度之活性成分配製物噴灑且移居褐飛蝨(brown planthopper)(褐飛蝨(Nilaparvata lugens))之幼蟲。
在所欲時間後,測定效力%。100%意指所有的褐飛蝨已被殺死;0%意指沒有褐飛蝨被殺死。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
稻綠蝽(Nezara viridula)-噴灑試驗(NEZARA)
溶劑:52.5重量份丙酮7重量份的二甲基甲醯胺
乳化劑:烷基芳基聚乙二醇醚
為了製造適當的活性成分配製物,將1重量份活性成分以指定重量份之溶劑溶解並以含1000ppm的乳化劑濃度之水補足直到達成所欲濃度。為了製造另外的試驗濃度,將混合物以含有乳化劑的水稀釋。若需要添加銨鹽或/及滲透劑,則將此等各自以1000ppm之濃度加至製備溶液中。
將受到南方紅尾碧蝽(green shield bug)(稻綠蝽)的幼蟲感染之大麥植物(大麥(Hordeum vulgare))以所欲濃度之活性成分配製物噴灑。
在所欲時間後,測定效力%。100%意指所有的蟲子已被殺死;0%意指沒有蟲子被殺死。
在此試驗中,例如,相較於先前技術,下列來自製備例之化合物顯示優異的效力:參見表。
Claims (14)
- 一種式(I)化合物,
其中A 1 為氮、=N +(O -)-、或=C(R 5)-,A 2 為-N(R 6)-、氧或硫,R 1 為(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 1-C 6)-氰烷基、(C 1-C 6)-羥烷基、(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)-氰炔基、(C 3-C 8)-環烷基、(C 3-C 6)-鹵環烷基、(C 3-C 6)-氰環烷基、(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)-烷胺基、二-(C 1-C 6)-烷胺基、(C 3-C 8)-環烷胺基、(C 1-C 6)-烷羰胺基、(C 1-C 6)-烷硫基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷羰基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷羰基-(C 1-C 6)-烷基、(C 1-C 6)-烷氧羰基-(C 1-C 6)-烷基、(C 1-C 6)-鹵烷氧羰基-(C 1-C 6)-烷基、(C 1-C 6)-烷磺醯胺基、胺磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷胺磺醯基-(C 1-C 6)-烷基、二-(C 1-C 6)-烷胺磺醯基-(C 1-C 6)-烷基,或在各情況下為視情況相同或不同地經單-或多-芳基-、-雜芳 基-或-雜環基-取代之(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,其中芳基、雜芳基或雜環基可各自視情況相同或不同地經下列單-或多取代:鹵素、氰基、硝基、羥基、胺基、羧基、胺甲醯基、胺磺醯基、(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)-烷硫基、(C 1-C 6)-烷亞磺醯基、(C 1-C 6)-烷磺醯基、(C 1-C 6)-烷磺亞胺基(alkylsulfimino)、(C 1-C 6)-烷磺亞胺基-(C 1-C 6)-烷基、(C 1-C 6)-烷磺亞胺基-(C 2-C 6)-烷羰基、(C 1-C 6)-烷磺醯亞胺基(alkylsulfoximino)、(C 1-C 6)-烷磺醯亞胺基-(C 1-C 6)-烷基、(C 1-C 6)-烷磺醯亞胺基-(C 2-C 6)-烷羰基、(C 1-C 6)-烷氧羰基、(C 1-C 6)-烷羰基、(C 3-C 6)-三烷矽基或苯甲基,R 2 為選自下列之基團:-C(=O)-NR 11R 12、-C(=S)-NR 11R 12、-NR 11R 12、NR 11-C(=O)-R 8和-NR 11-C(=S)-R 8,R 3 為C 2-鹵烷基,R 4 為氫、氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C 1-C 6)-烷矽基、(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、氰基(C 3-C 8)-環烷基、(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 1-C 6)-氰烷基、(C 1-C 6)-羥烷基、羥羰基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷氧羰基-(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)-氰烯基、(C 2-C 6)-炔基、(C 2-C 6)-鹵炔基、(C 2-C 6)-氰炔基、(C 1-C 6)-烷氧基、(C 1-C 6)-鹵烷氧基、(C 1-C 6)-氰烷氧基、(C 1-C 6)-烷氧羰基-(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)-烷氧亞胺基、(C 1-C 6)-烷基-(C 1-C 6)-烷氧亞胺基、(C 1-C 6)-鹵烷基-(C 1-C 6)-烷氧亞胺基、(C 1-C 6)-烷硫基、(C 1-C 6)-鹵烷硫基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷硫基、(C 1-C 6)-烷硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷亞磺醯基、(C 1-C 6)-鹵烷亞磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷亞磺醯基、(C 1-C 6)-烷亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷磺醯基、(C 1-C 6)-鹵烷磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷磺醯基、(C 1-C 6)-烷磺醯基-(C 1-C 6)-烷基、 (C 1-C 6)-烷磺醯氧基、(C 1-C 6)-烷羰基、(C 1-C 6)-烷硫羰基、(C 1-C 6)-鹵烷羰基、(C 1-C 6)-烷羰氧基、(C 1-C 6)-烷氧羰基、(C 1-C 6)-鹵烷氧羰基、胺羰基、(C 1-C 6)-烷胺羰基、(C 1-C 6)-烷胺硫羰基、二-(C 1-C 6)-烷胺羰基、二-(C 1-C 6)-烷胺硫羰基、(C 2-C 6)-烯胺羰基、二-(C 2-C 6)-烯胺羰基、(C 3-C 8)-環烷胺羰基、(C 1-C 6)-烷磺醯胺基、(C 1-C 6)-烷胺基、二-(C 1-C 6)-烷胺基、胺磺醯基、(C 1-C 6)-烷胺磺醯基、二-(C 1-C 6)-烷胺磺醯基、(C 1-C 6)-烷磺醯亞胺基、胺硫羰基、(C 1-C 6)-烷胺硫羰基、二-(C 1-C 6)-烷胺硫羰基、(C 3-C 8)-環烷胺基、NHCO-(C 1-C 6)-烷基((C 1-C 6)-烷羰胺基),在各情況下為視情況地經單或多次相同或不同取代之芳基或雜芳基,其中(在雜芳基的情況下)至少一個羰基可視情況地存在且其中在各情況下可能的取代基如下:氰基、羧基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C 1-C 6)烷矽基、(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)氰烷基、(C 1-C 6)羥烷基、羥羰基-(C 1-C 6)-烷氧基、(C 1-C 6)烷氧羰基-(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)氰烯基、(C 2-C 6)炔基、(C 2-C 6)鹵炔基、(C 2-C 6)氰炔基、(C 1-C 6)烷氧基、(C 1-C 6)鹵烷氧基、(C 1-C 6)氰烷氧基、(C 1-C 6)烷氧羰基-(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)烷氧亞胺基、(C 1-C 6)烷基-(C 1-C 6)烷氧亞胺基、(C 1-C 6)鹵烷基-(C 1-C 6)烷氧亞胺基、(C 1-C 6)烷硫基、(C 1-C 6)鹵烷硫基、(C 1-C 6)烷氧基-(C 1-C 6)烷硫基、(C 1-C 6)烷硫基-(C 1-C 6)烷基、(C 1-C 6)烷亞磺醯基、(C 1-C 6)鹵烷亞磺醯基、(C 1-C 6)烷氧基-(C 1-C 6)烷亞磺醯基、(C 1-C 6)烷亞磺醯基-(C 1-C 6)烷基、(C 1-C 6)烷磺醯基、(C 1-C 6)鹵烷磺醯基、(C 1-C 6)烷氧基-(C 1-C 6)烷磺醯基、(C 1-C 6)烷磺醯基-(C 1-C 6)烷基、(C 1-C 6)烷磺醯氧基、(C 1-C 6)烷羰基、(C 1-C 6)鹵烷羰基、(C 1-C 6)烷羰氧基、(C 1-C 6)烷氧羰基、(C 1-C 6)鹵烷氧羰基、胺羰基、(C 1-C 6)烷胺羰基、二-(C 1-C 6)烷胺羰基、(C 2-C 6)烯胺羰基、二-(C 2-C 6)-烯胺羰基、(C 3-C 8)環烷 胺羰基、(C 1-C 6)烷磺醯胺基、(C 1-C 6)烷胺基、二-(C 1-C 6)烷胺基、胺磺醯基、(C 1-C 6)烷胺磺醯基、二-(C 1-C 6)烷胺磺醯基、(C 1-C 6)烷磺醯亞胺基、胺硫羰基、(C 1-C 6)烷胺硫羰基、二-(C 1-C 6)烷胺硫羰基、(C 3-C 8)環烷胺基、(C 1-C 6)烷羰胺基,R 5 為氫、氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C 1-C 6)-烷矽基、(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)-氰烷基、(C 1-C 6)-羥烷基、羥羰基-(C 1-C 6)-烷氧基、(C 1-C 6)-烷氧羰基-(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)-氰烯基、(C 2-C 6)-炔基、(C 2-C 6)-鹵炔基、(C 2-C 6)-氰炔基、(C 1-C 6)-烷氧基、(C 1-C 6)-鹵烷氧基、(C 1-C 6)-氰烷氧基、(C 1-C 6)-烷氧羰基-(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)-烷氧亞胺基、(C 1-C 6)-烷基-(C 1-C 6)-烷氧亞胺基、(C 1-C 6)-鹵烷基-(C 1-C 6)-烷氧亞胺基、(C 1-C 6)-烷硫基、(C 1-C 6)-鹵烷硫基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷硫基、(C 1-C 6)-烷硫基-(C 1-C 6)-烷基、(C 1-C 6)-烷亞磺醯基、(C 1-C 6)-鹵烷亞磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷亞磺醯基、(C 1-C 6)-烷亞磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷磺醯基、(C 1-C 6)-鹵烷磺醯基、(C 1-C 6)-烷氧基-(C 1-C 6)-烷磺醯基、(C 1-C 6)-烷磺醯基-(C 1-C 6)-烷基、(C 1-C 6)-烷磺醯氧基、(C 1-C 6)-烷羰基、(C 1-C 6)-烷硫羰基、(C 1-C 6)-鹵烷羰基、(C 1-C 6)-烷羰氧基、(C 1-C 6)-烷氧羰基、(C 1-C 6)-鹵烷氧羰基、胺羰基、(C 1-C 6)-烷胺羰基、(C 1-C 6)-烷胺硫羰基、二-(C 1-C 6)-烷胺羰基、二-(C 1-C 6)-烷胺硫羰基、(C 2-C 6)-烯胺羰基、二-(C 2-C 6)-烯胺羰基、(C 3-C 8)-環烷胺羰基、(C 1-C 6)-烷磺醯胺基、(C 1-C 6)-烷胺基、二-(C 1-C 6)-烷胺基、胺磺醯基、(C 1-C 6)-烷胺磺醯基、二-(C 1-C 6)-烷胺磺醯基、(C 1-C 6)-烷磺醯亞胺基、胺硫羰基、(C 1-C 6)-烷胺硫羰基、二-(C 1-C 6)-烷胺硫羰基、(C 3-C 8)-環烷胺基或-NHCO-(C 1-C 6)-烷基((C 1-C 6)-烷羰胺基),R 6 為(C 1-C 6)烷基、(C 1-C 6)鹵烷基、(C 1-C 6)氰烷基、(C 1-C 6)羥烷基、 (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、(C 1-C 6)烷硫基-(C 1-C 6)烷基、(C 1-C 6)鹵烷硫基-(C 1-C 6)烷基、(C 1-C 6)烷亞磺醯基-(C 1-C 6)烷基、(C 1-C 6)鹵烷亞磺醯基-(C 1-C 6)烷基、(C 1-C 6)烷磺醯基-(C 1-C 6)烷基、(C 1-C 6)鹵烷磺醯基-(C 1-C 6)烷基、(C 1-C 6)烷氧基-(C 1-C 6)烷硫基-(C 1-C 6)烷基、(C 1-C 6)烷氧基-(C 1-C 6)烷亞磺醯基-(C 1-C 6)烷基、(C 1-C 6)烷氧基-(C 1-C 6)烷磺醯基-(C 1-C 6)烷基、(C 1-C 6)烷羰基-(C 1-C 6)烷基、(C 1-C 6)鹵烷羰基-(C 1-C 6)烷基、(C 1-C 6)烷氧羰基-(C 1-C 6)烷基、(C 1-C 6)鹵烷氧羰基-(C 1-C 6)烷基、胺羰基-(C 1-C 6)烷基、(C 1-C 6)烷胺基-(C 1-C 6)烷基、二-(C 1-C 6)烷胺基-(C 1-C 6)烷基或(C 3-C 8)環烷胺基-(C 1-C 6)烷基,R 8 為胺基或在各情況下視情況經單一或多次相同或不同地取代之C 1-C 4-烷胺基、二-(C 1-C 4)-烷胺基、C 2-C 6-烯胺基、C 2-C 6-炔胺基、C 3-C 12-環烷胺基、C 3-C 12-環烷基-(C 1-C 6)-烷胺基、C 4-C 12-雙環烷胺基或肼基,其中該等取代基可獨立地選自鹵素、氰基、硝基、羥基、(C=O)OH、C 1-C 6-烷基、C 3-C 6-環烷基、C 1-C 4-烷氧基、C 1-C 4-鹵烷氧基、C 1-C 4-烷硫基、C 1-C 4-烷亞磺醯基、C 1-C 4-烷磺醯基、C 1-C 4-鹵烷硫基、C 1-C 4-鹵烷亞磺醯基、C 1-C 4-鹵烷磺醯基、C 2-C 6-烷氧羰基、C 2-C 6-烷羰基、C 1-C 6-烷硫羰基、C 1-C 6-鹵烷羰基、C 1-C 6-鹵烷硫羰基、C 1-C 6-烷羰胺基、胺羰基、C 1-C 6-烷胺羰基、二-(C 1-C 6)-烷胺羰基、胺硫羰基、C 1-C 6-烷胺硫羰基、二-(C 1-C 6)-烷胺硫羰基、C 3-C 6-三烷矽基、胺基、C 1-C 4-烷胺基、二-(C 1-C 4-烷基)胺基、C 3-C 6-環烷胺基、胺磺醯基、C 1-C 6-烷胺磺醯基、二-(C 1-C 6)-烷胺磺醯基、磺醯胺基、C 1-C 6-烷磺醯胺基及二-(C 1-C 6)-烷磺醯胺基,R 11、R 12 獨立地為氫或在各情況下視情況經單一或多次相同或不同 地取代之C 1-C 6-烷基、C 2-C 6-烯基、C 2-C 6-炔基、C 3-C 12-環烷基、C 3-C 12-環烷基-C 1-C 6-烷基或C 4-C 12-雙環烷基,其中該等取代基可獨立地選自鹵素、氰基、硝基、羥基、C 1-C 6-烷基、C 3-C 6-環烷基、C 1-C 4-烷氧基、C 1-C 4-鹵烷氧基、C 1-C 4-烷硫基、C 1-C 4-烷亞磺醯基、C 1-C 4-烷磺醯基、C 1-C 4-烷磺亞胺基、C 1-C 4-烷磺亞胺基-C 1-C 4-烷基、C 1-C 4-烷磺亞胺基-C 2-C 5-烷羰基、C 1-C 4-烷磺亞胺基、C 1-C 4-烷磺亞胺基-C 1-C 4-烷基、C 1-C 4-烷磺亞胺基-C 2-C 5-烷羰基、C 2-C 6-烷氧羰基、C 2-C 6-烷羰基、C 3-C 6-三烷矽基、胺基、C 1-C 4-烷胺基、二-(C 1-C 4-烷基)胺基、C 3-C 6-環烷胺基、苯環及3-或6-員芳族部分飽和或飽和的雜環,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自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、氰基、(C=O)OH、CONH 2、NO 2、OH、C 1-C 4-烷氧基、C 1-C 4-鹵烷氧基、C 1-C 4-烷硫基、C 1-C 4-烷亞磺醯基、C 1-C 4-烷磺醯基、C 1-C 4-鹵烷硫基、C 1-C 4-鹵烷亞磺醯基、C 1-C 4-鹵烷磺醯基、C 1-C 4-烷胺基、二-(C 1-C 4-烷基)胺基、C 3-C 6-環烷胺基、(C 1-C 6-烷基)羰基、(C 1-C 6-烷氧基)羰基、(C 1-C 6-烷基)胺羰基、二-(C 1-C 4-烷基)胺羰基、三-(C 1-C 2)烷矽基、(C 1-C 4-烷基)(C 1-C 4-烷氧基)亞胺基或R 11、R 12 獨立地為苯環或3-至6-員芳族部分飽和或飽和的雜環,其中該雜原子係選自N、S和O之群組,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自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、氰基、(C=O)OH、CONH 2、NO 2、OH、C 1-C 4-烷氧基、C 1-C 4-鹵烷氧基、C 1-C 4-烷硫基、C 1-C 4-烷亞磺醯基、C 1-C 4-烷磺醯基、C 1-C 4-鹵烷硫基、C 1-C 4-鹵烷亞磺醯基、C 1-C 4-鹵烷磺醯基、C 1-C 4-烷胺基、二-(C 1-C 4-烷基)胺基、C 3-C 6-環烷胺基、(C 1-C 6-烷基)羰基、(C 1-C 6-烷氧基)羰基、(C 1-C 6-烷基)胺羰基、 二-(C 1-C 4-烷基)胺羰基、三-(C 1-C 2)烷矽基及(C 1-C 4-烷基)(C 1-C 4-烷氧基)亞胺基,及n 為0、1或2。 - 根據請求項1之式(I)化合物,其特徵在於A 1 為氮、=N +(O -)-或=C(R 5)-,A 2 為-N(R 6)-或氧,R 1 為(C 1-C 4)烷基、(C 1-C 4)羥烷基、(C 1-C 4)鹵烷基、(C 1-C 4)氰烷基、(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)鹵炔氧基-(C 1-C 4)烷基、(C 2-C 4)鹵炔基、(C 2-C 4)氰炔基、(C 3-C 6)環烷基、(C 3-C 6)-鹵環烷基、(C 3-C 6)-氰環烷基、(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)烷胺基、二-(C 1-C 4)烷胺基、(C 3-C 6)環烷胺基、(C 1-C 4)烷羰基-胺基、(C 1-C 4)烷硫基-(C 1-C 4)烷基、(C 1-C 4)鹵烷硫基-(C 1-C 4)烷基、(C 1-C 4)烷亞磺醯基-(C 1-C 4)烷基、(C 1-C 4)鹵烷亞磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷羰基-(C 1-C 4)烷基、(C 1-C 4)鹵烷羰基-(C 1-C 4)烷基、(C 1-C 4)烷磺醯胺基,或在各情況下為視情況相同或不同地經單-或二-芳基-、-雜芳基-或-雜環基-取代之(C 1-C 4)烷基、(C 1-C 4)烷氧基、(C 2-C 4)烯基、(C 2-C 4)炔基或(C 3-C 6)環烷基,其中芳基、雜芳基或雜環基各自為視情況相同或不同地經以下單-或二取代:鹵素、氰基、胺甲醯基、胺磺醯基、(C 1-C 4)烷基、(C 3-C 4)環烷基、(C 1-C 4)烷氧基、C 1-C 4)鹵烷基、(C 1-C 4)鹵烷氧基、(C 1-C 4)烷硫基、(C 1-C 4)烷亞磺醯基、(C 1-C 4)烷磺醯基、(C 1-C 4)烷磺亞胺基,R 2 為-C(=O)-NR 11R 12、-C(=S)-NR 11R 12、-NR 11R 12、-NR 11-C(=O)-R 8或-NR 11-C(=S)-R 8,R 3 為C 2-鹵烷基,R 4 為氫、氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C 1-C 4)烷矽基、(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、氰基(C 3-C 8)-環烷基、(C 1-C 4)烷基、(C 1-C 4)鹵烷基、(C 1-C 4)氰烷基、(C 1-C 4)羥烷基、(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)氰烯基、(C 2-C 4)炔基、(C 2-C 4)鹵炔基、(C 2-C 4)氰炔基、(C 1-C 4)烷氧基、(C 1-C 4)鹵烷氧基、(C 1-C 4)氰烷氧基、(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)烷氧亞胺基、(C 1-C 4)烷基-(C 1-C 4)烷氧亞胺基、(C 1-C 4)鹵烷基-(C 1-C 4)烷氧亞胺基、(C 1-C 4)烷硫基、(C 1-C 4)鹵烷硫基、(C 1-C 4)烷硫基-(C 1-C 4)烷基、(C 1-C 4)烷亞磺醯基、(C 1-C 4)鹵烷亞磺醯基、(C 1-C 4)烷亞磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷磺醯基、(C 1-C 4)鹵烷磺醯基、(C 1-C 4)烷磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷磺醯氧基、(C 1-C 4)烷羰基、(C 1-C 4)鹵烷羰基、胺羰基、胺硫羰基、(C 1-C 4)烷胺羰基、二-(C 1-C 4)烷胺羰基、(C 1-C 4)烷磺醯胺基、(C 1-C 4)烷胺基、二-(C 1-C 4)烷胺基、胺磺醯基、(C 1-C 4)烷胺磺醯基、二-(C 1-C 4)烷胺磺醯基、胺硫羰基、NHCO-(C 1-C 4)烷基((C 1-C 4)烷羰胺基),及亦為苯基或雜芳基,彼等各自為視情況相同或不同地經單-或二取代,其中(在雜芳基的情況下)至少一個羰基可視情況地存在且其中在各情況下可能的取代基如下:氰基、鹵素、硝基、乙醯基、胺基、(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)氰烷基、(C 1-C 4)羥烷基、(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)氰烯基、(C 2-C 4)炔基、(C 2-C 4)鹵炔基、(C 2-C 4)氰炔基、(C 1-C 4)烷氧基、(C 1-C 4)鹵烷氧基、(C 1-C 4)氰烷氧基、(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)烷氧亞胺基、(C 1-C 4)烷基-(C 1-C 4)烷氧亞胺基、(C 1-C 4)鹵烷基-(C 1-C 4)烷氧亞胺基、(C 1-C 4)烷硫基、(C 1-C 4)鹵烷硫基、(C 1-C 4)烷硫基-(C 1-C 4)烷基、(C 1-C 4)烷亞磺醯基、(C 1-C 4)鹵烷亞磺醯基、(C 1-C 4)烷亞磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷磺醯基、(C 1-C 4)鹵烷磺醯基、(C 1-C 4)烷磺醯基 -(C 1-C 4)烷基、(C 1-C 4)烷磺醯氧基、(C 1-C 4)烷羰基、(C 1-C 4)鹵烷羰基、胺羰基、(C 1-C 4)烷胺羰基、二-(C 1-C 4)烷胺羰基、(C 1-C 4)烷磺醯胺基、(C 1-C 4)烷胺基、二-(C 1-C 4)烷胺基、胺磺醯基、(C 1-C 4)烷胺磺醯基、二-(C 1-C 4)烷胺磺醯基、NHCO-(C 1-C 4)烷基((C 1-C 4)烷羰胺基),R 5 為氫、氰基、鹵素、硝基、乙醯基、羥基、胺基、SCN、三-(C 1-C 4)烷矽基、(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)氰烷基、(C 1-C 4)羥烷基、(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)氰烯基、(C 2-C 4)炔基、(C 2-C 4)鹵炔基、(C 2-C 4)氰炔基、(C 1-C 4)烷氧基、(C 1-C 4)鹵烷氧基、(C 1-C 4)氰烷氧基、(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)烷氧亞胺基、(C 1-C 4)烷基-(C 1-C 4)烷氧亞胺基、(C 1-C 4)鹵烷基-(C 1-C 4)烷氧亞胺基、(C 1-C 4)烷硫基、(C 1-C 4)鹵烷硫基、(C 1-C 4)烷硫基-(C 1-C 4)烷基、(C 1-C 4)烷亞磺醯基、(C 1-C 4)鹵烷亞磺醯基、(C 1-C 4)烷亞磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷磺醯基、(C 1-C 4)鹵烷磺醯基、(C 1-C 4)烷磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷磺醯氧基、(C 1-C 4)烷羰基、(C 1-C 4)鹵烷羰基、胺羰基、胺硫羰基、(C 1-C 4)烷胺羰基、二-(C 1-C 4)烷胺羰基、(C 1-C 4)烷磺醯胺基、(C 1-C 4)烷胺基、二-(C 1-C 4)烷胺基、胺磺醯基、(C 1-C 4)烷胺磺醯基、二-(C 1-C 4)烷胺磺醯基、胺硫羰基或NHCO-(C 1-C 4)烷基((C 1-C 4)烷羰胺基),R 6 為(C 1-C 4)烷基、(C 1-C 4)鹵烷基、(C 1-C 4)氰烷基、(C 1-C 4)羥烷基、(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)烷硫基-(C 1-C 4)烷基、(C 1-C 4)鹵烷硫基-(C 1-C 4)烷基、(C 1-C 4)烷亞磺醯基-(C 1-C 4)烷基、(C 1-C 4)鹵烷亞 磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷磺醯基-(C 1-C 4)烷基、(C 1-C 4)鹵烷磺醯基-(C 1-C 4)烷基、(C 1-C 4)烷氧基-(C 1-C 4)烷硫基-(C 1-C 4)烷基或(C 1-C 4)烷羰基-(C 1-C 4)烷基,R 8 為胺基,在各情況下視情況經單一或多次相同或不同地取代之C 1-C 4-烷胺基、二-(C 1-C 4)-烷胺基、C 2-C 6-烯胺基、C 2-C 6-炔胺基、C 3-C 12-環烷胺基、C 3-C 12-環烷基-(C 1-C 6)-烷胺基、C 4-C 12-雙環烷胺基或肼基,其中該等取代基可獨立地選自鹵素、氰基、胺基、C 1-C 6-烷基、C 3-C 6-環烷基、C 1-C 4-烷氧基、C 1-C 4-烷硫基、C 1-C 4-烷亞磺醯基、C 1-C 4-烷磺醯基、苯環及3-至6-員芳族部分飽和或飽和的雜環,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自C 1-C 4-烷基、C 1-C 4-鹵烷基、鹵素、氰基、NO 2、C 1-C 4-烷氧基或C 1-C 4-鹵烷氧基、或R 11、R 12 獨立地為氫、在各情況下視情況經單一或多次相同或不同地取代之C 1-C 4-烷基或C 3-C 6-環烷基,其中該等取代基可獨立地選自鹵素、氰基、苯環及3-至6-員芳族部分飽和或飽和的雜環,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自C 1-C 4-烷基、C 1-C 4-鹵烷基、鹵素、氰基、NO 2、C 1-C 4-烷氧基或C 1-C 4-鹵烷氧基、或R 11、R 12 獨立地為苯環或3-至6-員芳族部分飽和或飽和的雜環,其中該雜原子係選自N、S、O之群組,其中該苯環或雜環在各情況下可視情況相同或不同地經單-或多取代,且其中該等取代基可獨立地選自C 1-C 4-烷基、C 1-C 4-鹵烷基、鹵素或氰基,及n 為0、1或2。
- 根據請求項1之式(I)化合物,其特徵在於A 1 為氮或=C(R 5)-,A 2 為-N(R 6)-,R 1 為(C 1-C 4)-烷基、(C 1-C 4)-羥烷基、(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)-烷硫基-(C 1-C 4)-烷基、(C 1-C 4)-烷亞磺醯基-(C 1-C 4)-烷基或(C 1-C 4)-烷磺醯基-(C 1-C 4)-烷基,R 2 為-C(=O)-NR 11R 12、-C(=S)-NR 11R 12、-NR 11R 12、-NR 11-C(=O)-R 8或-NR 11-C(=S)-R 8,R 3 為C 2-鹵烷基,R 4 為氫、氰基、鹵素、硝基、羥基、胺基、(C 3-C 6)環烷基、氰基(C 3-C 8)-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)氰烯基、(C 2-C 4)炔基、(C 2-C 4)鹵炔基、(C 2-C 4)氰炔基、(C 1-C 4)烷氧基、(C 1-C 4)鹵烷氧基、(C 1-C 4)氰烷氧基、(C 1-C 4)烷硫基、(C 1-C 4)鹵烷硫基、(C 1-C 4)烷亞磺醯基、(C 1-C 4)鹵烷亞磺醯基、(C 1-C 4)烷磺醯基或(C 1-C 4)鹵烷磺醯基,R 5 為氫、鹵素、氰基或(C 1-C 4)烷基,R 6 為(C 1-C 4)烷基或(C 1-C 4)烷氧基-(C 1-C 4)烷基,R 8 為胺基,在各情況下可視情況地經單-鹵素-、-氰基-、-C 1-C 4-烷氧基-、-C 1-C 4-烷硫基-、-C 1-C 4-烷亞磺醯基-、-C 1-C 4-烷磺醯基-、-苯基-或-吡啶基-取代之(C 1-C 4)烷胺基、二-(C 1-C 4)-烷胺基、(C 2-C 6)-烯胺基、(C 2-C 4)-炔胺基、(C 3-C 6)-環烷胺基或肼基,R 11、R 12 獨立地為氫、在各情況下視情況地經單-鹵素-、-氰基-、-苯基-或-吡啶基-取代之(C 1-C 4)烷基或(C 3-C 6)環烷基及n 為0、1或2。
- 根據請求項1之式(I)化合物,其特徵在於A 1 為氮或=C(R 5)-,A 2 為-N(R 6)-,R 1 為(C 1-C 4)烷基、(C 1-C 4)鹵烷基或(C 3-C 6)環烷基,R 2 為-C(=O)-NR 11R 12,其中R 11、R 12 各自獨立地為氫、(C 1-C 4)烷基或(C 3-C 6)環烷基或R 2 為-NR 11-C(=O)-R 8,其中 R 8 為(C 2-C 6)-烯胺基、(C 2-C 4)-炔胺基、(C 3-C 6)-環烷胺基、(C 1-C 4)-烷胺基或肼基及R 11 為氫、(C 3-C 6)環烷基或(C 1-C 4)烷基,R 3 為氟乙基、二氟乙基、三氟乙基、四氟乙基或五氟乙基,R 4 為氫、氰基、鹵素、(C 1-C 4)烷基、(C 1-C 4)鹵烷基、(C 1-C 4)鹵烷氧基、(C 1-C 4)烷硫基、(C 1-C 4)烷亞磺醯基、(C 1-C 4)烷磺醯基、(C 1-C 4)鹵烷硫基、(C 1-C 4)鹵烷亞磺醯基、(C 1-C 4)鹵烷磺醯基或(C 1-C 4)烷羰胺基,R 5 為氫、氟、氯、溴或氰基,R 6 為甲基、乙基、異丙基、甲氧基甲基或甲氧基乙基及n 為0、1或2。
- 根據請求項1之式(I)化合物,其特徵在於A 1 為氮,A 2 為-NMe,R 1 為甲基、乙基、正丙基、異丙基或環丙基,R 2 為-C(=O)-NR 11R 12,其中R 11 為氫或(C 1-C 4)烷基及R 12 為氫、(C 1-C 4)烷基或(C 3-C 6)環烷基,或R 2 為-NR 11-C(=O)-R 8,其中R 8 為(C 1-C 4)烷胺基或二-(C 1-C 4)烷胺基及R 11 為氫或(C 1-C 4)烷基及R 3 為五氟乙基或四氟乙基(-CF 2CF 2H或CFHCF 3),R 4 為氫及n 為0或2。
- 根據請求項1之式(I)化合物,其特徵在於A 1 為氮,A 2 為-NMe,R 1 為乙基或甲基, R 2 為-C(=O)-NR 11R 12,其中R 11 為氫或甲基及R 12 為氫、甲基、環丙基或乙基或R 2 為-NR 11-C(=O)-R 8,其中R 8 為甲胺基(-NHMe)、乙胺基(-NHEt)或二甲胺基(-N(Me) 2)及R 11 為氫或甲基及R 3 為五氟乙基,R 4 為氫及n 為2。
- 一種式(I-1)化合物,
其中R 1、R 2、R 3、R 4和n係如請求項1至6中任一項中所定義。 - 一種式(I-1)化合物,
其中R 1、R 2、R 4和n係如請求項1至6中任一項中所定義。 - 根據請求項1至5中任一項之式(I)化合物,其特徵在於R 3為五氟乙基。
- 一種式(I-a)至(I-o)之化合物,
。 - 一種農化配製物,其包含至少一種根據請求項1至10中任一項之式(I)化合物及亦包含增量劑及/或界面活性劑。
- 根據請求項11之農化配製物,其另外包含其他農化活性成分。
- 一種控制動物害蟲之方法,其特徵在於使根據請求項1至10中任一項之式(I)化合物或根據請求項11或12之農化配製物作用於動物害蟲及/或其棲息地。
- 一種根據請求項1至10中任一項之式(I)化合物或根據請求項11或12之農化配製物的用途,其係用於控制動物害蟲。
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| JP7119004B2 (ja) * | 2017-05-02 | 2022-08-16 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としての2-(ヘタ)アリール置換縮合二環式ヘテロ環式誘導体 |
| WO2021033141A1 (en) | 2019-08-20 | 2021-02-25 | Pi Industries Ltd. | Fused heterocyclic compounds and their use as pest control agents |
| MX2022002649A (es) | 2019-09-12 | 2022-04-06 | Nihon Nohyaku Co Ltd | Insecticida agricola u horticola o agente de control de ectoparasitos o endoparasitos de animales que comprende cada uno un compuesto de imidazopiridazina que tiene un grupo ciclopropano-oxadiazol sustituido o una sal del mismo como ingrediente activo, y metodo para usar el insecticida o el agente de control. |
| CN120882309A (zh) | 2023-03-14 | 2025-10-31 | 先正达农作物保护股份公司 | 对杀昆虫剂具有抗性的有害生物的控制 |
| WO2025026738A1 (en) | 2023-07-31 | 2025-02-06 | Bayer Aktiengesellschaft | 6-[5-(ethylsulfonyl)-1-methyl-1h-imidazol-4-yl]-7-methyl-3-(pentafluoroethyl)-7h-imidazo[4,5-c]pyridazine derivatives as pesticides |
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-
2018
- 2018-04-25 JP JP2019559690A patent/JP7119003B2/ja active Active
- 2018-04-25 WO PCT/EP2018/060568 patent/WO2018202494A1/de not_active Ceased
- 2018-04-25 KR KR1020197035056A patent/KR20200003047A/ko not_active Ceased
- 2018-04-25 EP EP18718480.9A patent/EP3619213A1/de not_active Withdrawn
- 2018-04-25 BR BR112019022837-3A patent/BR112019022837A2/pt not_active Application Discontinuation
- 2018-04-25 CN CN201880028858.5A patent/CN110573513B/zh not_active Expired - Fee Related
- 2018-04-25 US US16/609,631 patent/US11089783B2/en not_active Expired - Fee Related
- 2018-04-27 TW TW107114385A patent/TW201906842A/zh unknown
- 2018-05-02 UY UY0001037720A patent/UY37720A/es not_active Application Discontinuation
- 2018-05-02 AR ARP180101126A patent/AR111742A1/es unknown
Also Published As
| Publication number | Publication date |
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| BR112019022837A2 (pt) | 2020-05-26 |
| CN110573513B (zh) | 2022-08-09 |
| US20200146293A1 (en) | 2020-05-14 |
| EP3619213A1 (de) | 2020-03-11 |
| JP2020518585A (ja) | 2020-06-25 |
| UY37720A (es) | 2018-11-30 |
| US11089783B2 (en) | 2021-08-17 |
| KR20200003047A (ko) | 2020-01-08 |
| WO2018202494A1 (de) | 2018-11-08 |
| JP7119003B2 (ja) | 2022-08-16 |
| AR111742A1 (es) | 2019-08-14 |
| CN110573513A (zh) | 2019-12-13 |
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