CN101516851A - 喹啉基甲基化合物 - Google Patents
喹啉基甲基化合物 Download PDFInfo
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- CN101516851A CN101516851A CNA2007800338478A CN200780033847A CN101516851A CN 101516851 A CN101516851 A CN 101516851A CN A2007800338478 A CNA2007800338478 A CN A2007800338478A CN 200780033847 A CN200780033847 A CN 200780033847A CN 101516851 A CN101516851 A CN 101516851A
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- alkyl
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- -1 Quinolinylmethyl compounds Chemical class 0.000 title claims abstract description 239
- 150000001875 compounds Chemical class 0.000 claims abstract description 364
- 239000000203 mixture Substances 0.000 claims abstract description 94
- 150000003839 salts Chemical class 0.000 claims abstract description 74
- 238000000034 method Methods 0.000 claims abstract description 52
- 241000244206 Nematoda Species 0.000 claims abstract description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- 241000238421 Arthropoda Species 0.000 claims abstract description 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims description 142
- 241001465754 Metazoa Species 0.000 claims description 69
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 50
- 239000000463 material Substances 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 239000003795 chemical substances by application Substances 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 241000238631 Hexapoda Species 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000002689 soil Substances 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 241000239290 Araneae Species 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 230000003071 parasitic effect Effects 0.000 claims description 9
- 230000000590 parasiticidal effect Effects 0.000 claims description 9
- 239000002297 parasiticide Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000012010 growth Effects 0.000 claims description 7
- 239000011630 iodine Substances 0.000 claims description 7
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 6
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims description 6
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 claims description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- 239000005864 Sulphur Substances 0.000 claims description 5
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 claims description 5
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- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- VSVKOUBCDZYAQY-UHFFFAOYSA-N 7-chloro-1,2-benzothiazole Chemical compound ClC1=CC=CC2=C1SN=C2 VSVKOUBCDZYAQY-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 206010061217 Infestation Diseases 0.000 claims description 4
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000002452 interceptive effect Effects 0.000 claims description 4
- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003477 4 aminobutyric acid receptor stimulating agent Chemical class 0.000 claims description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005901 Flubendiamide Substances 0.000 claims description 3
- 102100030643 Hydroxycarboxylic acid receptor 2 Human genes 0.000 claims description 3
- 101710125793 Hydroxycarboxylic acid receptor 2 Proteins 0.000 claims description 3
- 102000008109 Mixed Function Oxygenases Human genes 0.000 claims description 3
- 108010074633 Mixed Function Oxygenases Proteins 0.000 claims description 3
- 229940087098 Oxidase inhibitor Drugs 0.000 claims description 3
- ZBXICRCDECBVDN-UHFFFAOYSA-N [P].[S].[F].N1C=CC=C1 Chemical compound [P].[S].[F].N1C=CC=C1 ZBXICRCDECBVDN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
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- 238000005266 casting Methods 0.000 claims description 3
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003630 growth substance Substances 0.000 claims description 3
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical compound N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 claims description 2
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
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- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
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- GRDUWPCIOSTLCK-UHFFFAOYSA-N 4-phenyl-n-(quinolin-4-ylmethyl)benzenesulfonamide Chemical class C=1C=NC2=CC=CC=C2C=1CNS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GRDUWPCIOSTLCK-UHFFFAOYSA-N 0.000 abstract 1
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- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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Abstract
本发明涉及式(I)的新型联苯-4-磺酸(喹啉-4-基甲基)酰胺化合物,其中R1和R2为卤素、OH、CN、NH2、NO2、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基等;R3、R4、R5、R6为卤素、H、CN、NH2、NO2、OH、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基等;m为0、1、2、3、4或5;且n为1或2;及其N-氧化物和盐,涉及它们在防治节肢动物害虫和线虫中的用途,还涉及包含这些化合物作为活性组分的组合物。本发明还涉及防治节肢动物害虫或线虫害虫的方法。
Description
本发明涉及新型的联苯-4-磺酸(喹啉-4-基甲基)酰胺化合物及其N-氧化物和盐以及它们在防治节肢动物害虫和线虫中的用途,还涉及包含这类化合物作为活性组分的组合物。本发明还涉及一种防治节肢动物害虫或线虫的方法。
动物害虫以及尤其是节肢动物和线虫损坏生长和收获的作物并攻击木质居住和商业结构体,从而对食物供应和财产造成大的经济损失。尽管已知大量杀虫剂,但由于目标害虫对所述试剂产生抗药性的能力,仍需要防治节肢动物和线虫的新试剂。因此,本发明的目的是提供对大量不同的动物害虫,尤其是难以防治的昆虫、蜘蛛和线虫具有良好杀虫活性并且显示出宽活性谱的化合物。
WO 2005/033081描述了杀真菌的4-吡啶基甲基磺酰胺衍生物。这些化合物可以带有与吡啶结构部分稠合的苯环。
WO 2006/097489(PCT/EP/2006/060753)描述了联苯磺酸的各种4-吡啶基甲基酰胺,其中联苯基结构部分可以在磺酰胺基团处的联苯基结构部分的苯基环上带有取代基。这些化合物用于防治节肢动物害虫并保护材料以免被所述害虫侵袭和/或破坏。
WO 2006/097488(PCT/EP/2006/060752)尤其描述了式(A)的杀节肢动物的喹诺酮化合物:
其中R2和R3均为氢、卤素、甲氧基或三氟甲氧基,R1为氢或甲基且Ra选自可以未被取代或可以带有一个选自氯、C1-C4烷基、甲氧基、三氟甲氧基或苯基的取代基的苯基。
US 60/782429描述了在磺酰胺基团上带有联苯基结构部分的特定喹啉甲基磺酰胺,其中联苯基的亚苯基结构部分未被取代。
仍需要提供可以用于防治有害节肢动物如昆虫和蜘蛛的化合物。希望这些化合物对有害节肢动物具有改进的作用和/或更宽的活性谱。
惊人的是已经发现该目的由式(I)的喹啉化合物及其N-氧化物或盐实现:
其中
R1、R2各自独立地为卤素、羟基、氰基、氨基、硝基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C4烷氧基-C1-C4烷氧基、C3-C7环烷基-C1-C4烷氧基、C(OH)(CF3)2、C1-C6卤代烷基、C2-C6卤代链烯基、C1-C6卤代烷氧基、C2-C6卤代链烯氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C(Ra)=O或C(Ra)=NORb;
Ra为氢或C1-C4烷基;
Rb为氢、C1-C4烷基、C2-C4链烯基、C2-C4炔基、C1-C4卤代烷基或C2-C4卤代链烯基;
R3、R4、R5、R6各自独立地为氢、卤素、氰基、氨基、硝基、羟基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基或C(=O)ORc;
Rc为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基;
m为0、1、2、3、4或5;
n为1或2。
因此,本发明涉及通式(I)的喹啉化合物及其N-氧化物和盐。
本发明化合物还可以用于防治节肢动物害虫和线虫害虫。因此,本发明还涉及通式(I)的喹啉化合物及其N-氧化物和盐在防治节肢动物害虫或线虫害虫中的用途。
本发明进一步涉及一种防治节肢动物害虫或线虫的方法,包括使昆虫、蜘蛛或线虫或其食物供应源、栖息地、繁殖地或其场所与至少一种式(I)化合物和/或其N-氧化物或盐接触。此外,本发明还涉及一种保护生长中的植物免受节肢动物害虫或线虫侵袭或侵染的方法,包括向植物或它们生长的土壤或水体中施用至少一种式(I)化合物和/或其N-氧化物或可农用盐。在上述方法的优选实施方案中,至少一种式(I)化合物和/或其N-氧化物或盐或包含它们的组合物按照式(I)化合物计算以5-2000g/ha的量施用。
此外,本发明还涉及一种用至少一种式(I)化合物和/或其N-氧化物或可农用盐或以杀虫有效量包含这些化合物(I)中的至少一种的组合物保护种子的方法。优选至少一种式(I)化合物和/或其N-氧化物或可农用盐或包含至少一种这些化合物的组合物以0.1g-10kg/100kg种子的量施用。
因此,本发明的另一目的是种子,其包含至少一种式(I)化合物和/或其N-氧化物或可农用盐,优选以0.1g-10kg/100kg种子的量包含式(I)化合物和/或其N-氧化物或盐(以式(I)化合物计算)。
本发明还涉及一种处理、防治、预防或保护动物免受寄生虫侵袭或侵染的方法,包括对动物给药或施用杀寄生虫有效量的至少一种式(I)化合物和/或其N-氧化物或可兽用盐。
本发明还涉及协同增效杀虫混合物,包含式(I)化合物和/或其N-氧化物或盐和选自如下的杀虫剂:有机(硫代)磷酸酯,氨基甲酸酯,拟除虫菊酯,生长调节剂,新烟碱(neonicotinoids),烟酸受体激动剂/拮抗剂化合物,GABA拮抗剂化合物,大环内酯杀虫剂,METI I、II和III化合物,氧化磷酸化抑制剂化合物,蜕皮干扰剂(moulting disruptor)化合物,混合功能氧化酶抑制剂化合物,钠通道阻断剂化合物,benclothiaz,联苯肼酯(bifenazate),杀螟丹(cartap),氟啶虫酰胺(flonicamid),啶虫丙醚(pyridalyl),拒嗪酮(pymetrozine),硫,硫环杀(thiocyclam),氟虫酰胺(flubendiamide),cyanopyrafen,吡氟硫磷(flupyrazofos),丁氟螨酯(cyflumetofen),amidoflumet,邻氨基苯甲酰胺(anthranilamide)和N-R′-2,2-二halo-1-R″-环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙或N-R′-2,2-二(R′″)-丙酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙,其中R′为甲基或乙基,halo为氯或溴,R″为氢或甲基且R′″为甲基或乙基。
取决于取代方式,式(I)化合物及其N-氧化物可能具有一个或多个手性中心,此时它们以纯对映体或纯非对映体或以对映体或非对映体混合物存在。纯对映体或非对映体及其混合物均为本发明主题。
化合物(I)的可农用盐尤其包括其阳离子和阴离子分别对化合物(I)的杀虫作用没有不利影响的那些阳离子的盐或那些酸的酸加成盐。合适的阳离子因此尤其是碱金属离子,优选钠和钾离子,碱土金属离子,优选钙、镁和钡离子,过渡金属离子,优选锰、铜、锌和铁离子,以及需要的话可以带有1-4个C1-C4烷基取代基和/或一个苯基或苄基取代基的铵离子,优选二异丙基铵、四甲基铵、四丁基铵、三甲基苄基铵,此外还有鏻离子,锍离子,优选三(C1-C4烷基)锍,以及氧化锍离子,优选三(C1-C4烷基)氧化锍。
有用酸加成盐的阴离子主要是氯离子、溴离子、氟离子、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根以及C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。它们可以通过使式(I)化合物与对应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
式(I)化合物的可兽用盐尤其包括在形成兽用盐的领域中已知且被接受的那些阳离子的盐或酸加成盐。例如由含有碱性氮原子如氨基的式(I)化合物形成的合适酸加成盐包括与无机酸的盐,例如盐酸盐、硫酸盐、磷酸盐和硝酸盐以及有机酸的盐,所述有机酸如乙酸、马来酸(例如马来酸的单酸盐或二酸盐)、二马来酸、富马酸(例如富马酸的单酸盐或二酸盐)、二富马酸、甲烷次磺酸、甲烷磺酸和琥珀酸。
在上面所给变量的定义中,使用通常为所述取代基的代表的集合性术语。术语Cn-Cm表示每种情况下在所述取代基或取代基结构部分中的可能碳原子数目。
本文所用术语“卤素”指氟、氯、溴和碘。
本文所用术语“烷基”指具有1-6个碳原子的直链或支化饱和烃基,例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基。
本文所用术语“卤代烷基”指具有1-6个碳原子的直链或支化烷基(如上所述),其中这些基团中的部分或所有氢原子可以被上述卤原子代替,例如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基和五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、CH2-C2F5、CF2-C2F5、CF(CF3)2、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基、九氟丁基、5-氟-1-戊基、5-氯-1-戊基、5-溴-1-戊基、5-碘-1-戊基、5,5,5-三氯-1-戊基、十一氟戊基、6-氟-1-己基、6-氯-1-己基、6-溴-1-己基、6-碘-1-己基、6,6,6-三氯-1-己基或十二氟己基。
因此,本文所用的“烷氧基”和“烷硫基”指具有1-6个碳原子的直链或支化烷基(如上所述),其分别通过氧原子或硫原子在该烷基的任意位置键合。实例包括甲氧基、乙氧基、丙氧基、异丙氧基、甲硫基、乙硫基、丙硫基、异丙硫基和正丁硫基。
类似地,“烷基亚磺酰基”和“烷基磺酰基”指具有1-6个碳原子的直链或支化烷基(如上所述),其分别通过-S(=O)-结构部分或-S(=O)2-结构部分在该烷基的任意位置键合。实例包括甲基亚磺酰基和甲基磺酰基。
类似地,“卤代烷氧基”和“卤代烷硫基”(或卤代烷基硫基)指具有1-6个碳原子的直链或支化烷基(如上所述),其分别通过氧原子或硫原子在该烷基的任意位置键合,其中这些基团中的部分或所有氢原子可以被上述卤原子代替,例如C1-C2卤代烷氧基,如氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基和五氟乙氧基,还有C1-C2卤代烷硫基,如氯甲硫基、溴甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基、二氯氟甲硫基、氯二氟甲硫基、1-氯乙硫基、1-溴乙硫基、1-氟乙硫基、2-氟乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、2,2,2-三氯乙硫基和五氟乙硫基等。
本文所用术语“C1-C4烷氧基-C1-C4烷氧基”指具有1-4个碳原子的烷氧基(如上所述),其中烷氧基的一个氢原子被C1-C4烷氧基代替。
本文所用术语“链烯基”指具有2-6个碳原子和在任意位置的双键的支化或未支化的不饱和烃基,如乙烯基、1-丙烯基、2-丙烯基、1-甲基-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基;
本文所用术语“炔基”指具有2-6个碳原子且含有至少一个叁键的支化或未支化的不饱和烃基,如乙炔基、丙炔基、1-丁炔基、2-丁炔基等。
类似地,“链烯氧基”和“炔氧基”分别指直链或支化链烯基或炔基(如上所述),其通过氧原子在链烯基的任意碳原子处或在炔基的任意碳原子处键合,例如烯丙氧基或炔丙氧基。
本文所用术语“环烷基”指单环3-7员饱和碳原子环,如环丙基、环丁基、环戊基、环己基或环庚基。
本文所用术语“C3-C7环烷基-C1-C4烷基”指具有1-4个碳原子的烷基(如上所述),其中该烷基的一个氢原子被C3-C7环烷基代替。
类似地,本文所用术语“C3-C7环烷基-C1-C4烷氧基”指具有1-4个碳原子的烷氧基(如上所述),其中该烷氧基的一个氢原子被C3-C7环烷基代替。
对于式(I)化合物的意欲用途,特别优选取代基R1-R6以及变量n和m的下列含义,在每种情况下单独或组合:
优选如下式(I)化合物,其中R1独立地选自卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基磺酰基或C1-C6卤代烷基磺酰基。特别优选如下式(I)化合物,其中R1独立地选自卤素,尤其是F、Cl、Br;C1-C2烷基,尤其是CH3,C1-C2卤代烷基,尤其是C1-C2氟烷基,如CHF2、CF3,C1-C2烷氧基,尤其是OCH3,以及C1-C2卤代烷氧基,尤其是C1-C2氟烷氧基,如OCHF2和OCF3;
优选其中m为1、2或3的式(I)化合物;
优选如下式(I)化合物,其中R2相互独立地选自卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基磺酰基或C1-C6卤代烷基磺酰基。特别优选如下式(I)化合物,其中R2独立地选自卤素,尤其是F、Cl、Br;C1-C2烷基,尤其是CH3,C1-C3卤代烷基,尤其是C1-C3氟烷基,如CHF2、CF3和CF(CF3)2;C1-C2烷氧基,尤其是OCH3,以及C1-C3卤代烷氧基,尤其是C1-C3氟烷氧基,如OCHF2、OCF3、OCF(CF3)2;
优选其中R3、R4、R5、R6各自独立地选自氢、卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基或C1-C6烷硫基的式(I)化合物。
本发明非常优选的实施方案涉及其中R3、R4、R5、R6各自为氢的式(I)化合物。
本发明的另一优选实施方案涉及其中n为1的式(I)化合物。
本发明非常优选的实施方案涉及其中取代基R1在相对于磺酰胺结构部分的间位连接于苯基上的式(I)化合物。该化合物也称为式(I.1)化合物,其中联苯基结构部分具有下列方案中的取代方式,并且R1、R2、R3、R4、R5、R6和m如上对式(I)化合物所定义:
熟练技术人员易于理解就式(I)化合物对R1-R6和m所给的优选情形也适用于下面所定义的式(I.1)和(I.1a)。
在式(I.1)化合物中,优选其中R1选自氟、氯、溴、甲基、甲氧基、三氟甲基、甲硫基、三氟甲硫基和三氟甲氧基的那些。
该类化合物的优选实施方案包括:
其中R3、R4、R5和R6如上所定义且m为0的式(I.1)化合物;
其中R2、R3、R4、R5和R6如上所定义且m为1的式(I.1)化合物;
其中R2、R3、R4、R5和R6如上所定义且m为2的式(I.1)化合物;
其中R2、R3、R4、R5和R6如上所定义且m为3的式(I.1)化合物。
还特别优选其中R1为F、Cl或Br的式(I.1)化合物。
进一步优选其中R2独立地选自卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基和C1-C6烷氧基的式(I.1)化合物。
在式(I.1)化合物中,特别优选如下式(I.1)化合物,其中R1在相对于磺酰胺结构部分的间位连接于苯基上,n为1且R3、R4、R5、R6各自为氢,该化合物在下面称为式(I.1.a)的喹啉化合物:
其中R1、R2和m具有上述含义,尤其是作为优选提到的含义。
本发明的另一非常优选的实施方案涉及如下式(I)化合物,其中取代基R1在相对于磺酰胺结构部分的邻位连接于苯基上。该化合物也称为式(I.2)化合物,其中联苯基结构部分具有下列方案中的取代方式且R1、R2、R3、R4、R5、R6和m如上对式(I)化合物所定义:
熟练技术人员易于理解就式(I)化合物对R1-R6和m所给的优选情形也适用于下面所定义的式(I.2)和(I.2.a)。
在式(I.2)化合物中,优选其中R1选自氟、氯、溴、甲基、甲氧基、三氟甲基、甲硫基、三氟甲硫基和三氟甲氧基的那些。
这类化合物的优选实施方案包括:
其中R3、R4、R5和R6如上所定义且m为0的式(I.2)化合物;
其中R2、R3、R4、R5和R6如上所定义且m为1的式(I.2)化合物;
其中R2、R3、R4、R5和R6如上所定义且m为2的式(I.2)化合物;
其中R2、R3、R4、R5和R6如上所定义且m为3的式(I.2)化合物。
还特别优选其中R1为F、Cl或Br的式(I.2)化合物。
进一步优选其中R2独立地选自卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基和C1-C6烷氧基的式(I.2)化合物。
在式(I.2)化合物中,特别优选如下式(I)化合物,其中R1在相对于磺酰胺结构部分的邻位连接于苯基上,n为1且R3、R4、R5、R6各自为氢,该化合物在下文中称为式(I.2.a)的喹啉化合物:
其中R1、R2和m具有上述含义,尤其是作为优选提到的含义。
合适的喹啉结构部分Q的实例在下表A中给出。
在式(Q)中,*表示与骨架的键合位置。
表A
喹啉结构部分编号 | R3 | R4 | R5 | R6 |
Q-1 | H | H | H | H |
Q-2 | F | H | H | H |
Q-3 | H | F | H | H |
Q-4 | H | H | F | H |
Q-5 | H | H | H | F |
Q-6 | Cl | H | H | H |
Q-7 | H | Cl | H | H |
喹啉结构部分编号 | R3 | R4 | R5 | R6 |
Q-8 | H | H | Cl | H |
Q-9 | H | H | H | Cl |
Q-10 | CH3 | H | H | H |
Q-11 | H | CH3 | H | H |
Q-12 | H | H | CH3 | H |
Q-13 | H | H | H | CH3 |
Q-14 | OCH3 | H | H | H |
Q-15 | H | OCH3 | H | H |
Q-16 | H | H | OCH3 | H |
Q-17 | H | H | H | OCH3 |
Q-18 | CF3 | H | H | H |
Q-19 | H | CF3 | H | H |
Q-20 | H | H | CF3 | H |
Q-21 | H | H | H | CF3 |
Q-22 | OCF3 | H | H | H |
Q-23 | H | OCF3 | H | H |
Q-24 | H | H | OCF3 | H |
Q-25 | H | H | H | OCF3 |
Q-26 | Cl | Cl | H | H |
Q-27 | Cl | H | Cl | H |
Q-28 | Cl | H | H | Cl |
Q-29 | H | Cl | Cl | H |
Q-30 | H | Cl | H | Cl |
Q-31 | H | H | Cl | Cl |
Q-32 | F | F | H | H |
Q-33 | F | H | F | H |
Q-34 | F | H | H | F |
Q-35 | H | F | F | H |
Q-36 | H | F | H | F |
Q-37 | H | H | F | F |
Q-38 | CH3 | CH3 | H | H |
Q-39 | CH3 | H | CH3 | H |
Q-40 | CH3 | H | H | CH3 |
Q-41 | H | CH3 | CH3 | H |
Q-42 | H | CH3 | H | CH3 |
Q-43 | H | H | CH3 | CH3 |
Q-44 | OCH3 | OCH3 | H | H |
Q-45 | OCH3 | H | OCH3 | H |
Q-46 | OCH3 | H | H | OCH3 |
Q-47 | H | OCH3 | OCH3 | H |
Q-48 | H | OCH3 | H | OCH3 |
喹啉结构部分编号 | R3 | R4 | R5 | R6 |
Q-49 | H | H | OCH3 | OCH3 |
Q-50 | CF3 | CF3 | H | H |
Q-51 | CF3 | H | CF3 | H |
Q-52 | CF3 | H | H | CF3 |
Q-53 | H | CF3 | CF3 | H |
Q-54 | H | CF3 | H | CF3 |
Q-55 | H | H | CF3 | CF3 |
对于其用途,特别优选汇编在下表中的式(I)化合物。此外,对表中取代基所提到的基团本身为所述取代基的特别优选实施方案,与其中提到它们的组合无关。
表1
其中Q表示Q-1且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表B
编号 | (R1)n | (R2)m |
A-1 | 2-F | - |
A-2 | 2-Cl | - |
A-3 | 2-CH3 | - |
A-4 | 2-CF3 | - |
A-5 | 2-OCH3 | - |
A-6 | 2-OCF3 | --- |
A-7 | 3-F | - |
A-8 | 3-Cl | - |
A-9 | 3-CH3 | - |
A-10 | 3-CF3 | - |
A-11 | 3-OCH3 | - |
A-12 | 3-OCF3 | --- |
A-13 | 2-F | 2-CH3 |
A-14 | 2-Cl | 2-CH3 |
A-15 | 2-CH3 | 2-CH3 |
A-16 | 2-CF3 | 2-CH3 |
A-17 | 2-OCH3 | 2-CH3 |
编号 | (R1)n | (R2)m |
A-18 | 2-OCF3 | 2-CH3 |
A-19 | 3-F | 2-CH3 |
A-20 | 3-Cl | 2-CH3 |
A-21 | 3-CH3 | 2-CH3 |
A-22 | 3-CF3 | 2-CH3 |
A-23 | 3-OCH3 | 2-CH3 |
A-24 | 3-OCF3 | 2-CH3 |
A-25 | 2-F | 2-CH2CH3 |
A-26 | 2-Cl | 2-CH2CH3 |
A-27 | 2-CH3 | 2-CH2CH3 |
A-28 | 2-CF3 | 2-CH2CH3 |
A-29 | 2-OCH3 | 2-CH2CH3 |
A-30 | 2-OCF3 | 2-CH2CH3 |
A-31 | 3-F | 2-CH2CH3 |
A-32 | 3-Cl | 2-CH2CH3 |
A-33 | 3-CH3 | 2-CH2CH3 |
A-34 | 3-CF3 | 2-CH2CH3 |
编号 | (R1)n | (R2)m |
A-35 | 3-OCH3 | 2-CH2CH3 |
A-36 | 3-OCF3 | 2-CH2CH3 |
A-37 | 2-F | 2-Br |
A-38 | 2-Cl | 2-Br |
A-39 | 2-CH3 | 2-Br |
A-40 | 2-CF3 | 2-Br |
A-41 | 2-OCH3 | 2-Br |
A-42 | 2-OCF3 | 2-Br |
A-43 | 3-F | 2-Br |
A-44 | 3-Cl | 2-Br |
A-45 | 3-CH3 | 2-Br |
A-46 | 3-CF3 | 2-Br |
A-47 | 3-OCH3 | 2-Br |
A-48 | 3-OCF3 | 2-Br |
A-49 | 2-F | 2-Cl |
A-50 | 2-Cl | 2-Cl |
A-51 | 2-CH3 | 2-Cl |
A-52 | 2-CF3 | 2-Cl |
A-53 | 2-OCH3 | 2-Cl |
A-54 | 2-OCF3 | 2-Cl |
A-55 | 3-F | 2-Cl |
A-56 | 3-Cl | 2-Cl |
A-57 | 3-CH3 | 2-Cl |
A-58 | 3-CF3 | 2-Cl |
A-59 | 3-OCH3 | 2-Cl |
A-60 | 3-OCF3 | 2-Cl |
A-61 | 2-F | 2-F |
A-62 | 2-Cl | 2-F |
A-63 | 2-CH3 | 2-F |
A-64 | 2-CF3 | 2-F |
A-65 | 2-OCH3 | 2-F |
A-66 | 2-OCF3 | 2-F |
A-67 | 3-F | 2-F |
A-68 | 3-Cl | 2-F |
A-69 | 3-CH3 | 2-F |
A-70 | 3-CF3 | 2-F |
A-71 | 3-OCH3 | 2-F |
A-72 | 3-OCF3 | 2-F |
A-73 | 2-F | 2-CN |
A-74 | 2-Cl | 2-CN |
编号 | (R1)n | (R2)m |
A-75 | 2-CH3 | 2-CN |
A-76 | 2-CF3 | 2-CN |
A-77 | 2-OCH3 | 2-CN |
A-78 | 2-OCF3 | 2-CN |
A-79 | 3-F | 2-CN |
A-80 | 3-Cl | 2-CN |
A-81 | 3-CH3 | 2-CN |
A-82 | 3-CF3 | 2-CN |
A-83 | 3-OCH3 | 2-CN |
A-84 | 3-OCF3 | 2-CN |
A-85 | 2-F | 2-NO2 |
A-86 | 2-Cl | 2-NO2 |
A-87 | 2-CH3 | 2-NO2 |
A-88 | 2-CF3 | 2-NO2 |
A-89 | 2-OCH3 | 2-NO2 |
A-90 | 2-OCF3 | 2-NO2 |
A-91 | 3-F | 2-NO2 |
A-92 | 3-Cl | 2-NO2 |
A-93 | 3-CH3 | 2-NO2 |
A-94 | 3-CF3 | 2-NO2 |
A-95 | 3-OCH3 | 2-NO2 |
A-96 | 3-OCF3 | 2-NO2 |
A-97 | 2-F | 2-OCH3 |
A-98 | 2-Cl | 2-OCH3 |
A-99 | 2-CH3 | 2-OCH3 |
A-100 | 2-CF3 | 2-OCH3 |
A-101 | 2-OCH3 | 2-OCH3 |
A-102 | 2-OCF3 | 2-OCH3 |
A-103 | 3-F | 2-OCH3 |
A-104 | 3-Cl | 2-OCH3 |
A-105 | 3-CH3 | 2-OCH3 |
A-106 | 3-CF3 | 2-OCH3 |
A-107 | 3-OCH3 | 2-OCH3 |
A-108 | 3-OCF3 | 2-OCH3 |
A-109 | 2-F | 2-CF3 |
A-110 | 2-Cl | 2-CF3 |
A-111 | 2-CH3 | 2-CF3 |
A-112 | 2-CF3 | 2-CF3 |
A-113 | 2-OCH3 | 2-CF3 |
A-114 | 2-OCF3 | 2-CF3 |
编号 | (R1)n | (R2)m |
A-115 | 3-F | 2-CF3 |
A-116 | 3-Cl | 2-CF3 |
A-117 | 3-CH3 | 2-CF3 |
A-118 | 3-CF3 | 2-CF3 |
A-119 | 3-OCH3 | 2-CF3 |
A-120 | 3-OCF3 | 2-CF3 |
A-121 | 2-F | 2-OCF3 |
A-122 | 2-Cl | 2-OCF3 |
A-123 | 2-CH3 | 2-OCF3 |
A-124 | 2-CF3 | 2-OCF3 |
A-125 | 2-OCH3 | 2-OCF3 |
A-126 | 2-OCF3 | 2-OCF3 |
A-127 | 3-F | 2-OCF3 |
A-128 | 3-Cl | 2-OCF3 |
A-129 | 3-CH3 | 2-OCF3 |
A-130 | 3-CF3 | 2-OCF3 |
A-131 | 3-OCH3 | 2-OCF3 |
A-132 | 3-OCF3 | 2-OCF3 |
A-133 | 2-F | 2-CF(CF3)2 |
A-134 | 2-Cl | 2-CF(CF3)2 |
A-135 | 2-CH3 | 2-CF(CF3)2 |
A-136 | 2-CF3 | 2-CF(CF3)2 |
A-137 | 2-OCH3 | 2-CF(CF3)2 |
A-138 | 2-OCF3 | 2-CF(CF3)2 |
A-139 | 3-F | 2-CF(CF3)2 |
A-140 | 3-Cl | 2-CF(CF3)2 |
A-141 | 3-CH3 | 2-CF(CF3)2 |
A-142 | 3-CF3 | 2-CF(CF3)2 |
A-143 | 3-OCH3 | 2-CF(CF3)2 |
A-144 | 3-OCF3 | 2-CF(CF3)2 |
A-145 | 2-F | 2-SCH3 |
A-146 | 2-Cl | 2-SCH3 |
A-147 | 2-CH3 | 2-SCH3 |
A-148 | 2-CF3 | 2-SCH3 |
A-149 | 2-OCH3 | 2-SCH3 |
A-150 | 2-OCF3 | 2-SCH3 |
A-151 | 3-F | 2-SCH3 |
A-152 | 3-Cl | 2-SCH3 |
A-153 | 3-CH3 | 2-SCH3 |
A-154 | 3-CF3 | 2-SCH3 |
编号 | (R1)n | (R2)m |
A-155 | 3-OCH3 | 2-SCH3 |
A-156 | 3-OCF3 | 2-SCH3 |
A-157 | 2-F | 3-CH3 |
A-158 | 2-Cl | 3-CH3 |
A-159 | 2-CH3 | 3-CH3 |
A-160 | 2-CF3 | 3-CH3 |
A-161 | 2-OCH3 | 3-CH3 |
A-162 | 2-OCF3 | 3-CH3 |
A-163 | 3-F | 3-CH3 |
A-164 | 3-Cl | 3-CH3 |
A-165 | 3-CH3 | 3-CH3 |
A-166 | 3-CF3 | 3-CH3 |
A-167 | 3-OCH3 | 3-CH3 |
A-168 | 3-OCF3 | 3-CH3 |
A-169 | 2-F | 3-CH2CH3 |
A-170 | 2-Cl | 3-CH2CH3 |
A-171 | 2-CH3 | 3-CH2CH3 |
A-172 | 2-CF3 | 3-CH2CH3 |
A-173 | 2-OCH3 | 3-CH2CH3 |
A-174 | 2-OCF3 | 3-CH2CH3 |
A-175 | 3-F | 3-CH2CH3 |
A-176 | 3-Cl | 3-CH2CH3 |
A-177 | 3-CH3 | 3-CH2CH3 |
A-178 | 3-CF3 | 3-CH2CH3 |
A-179 | 3-OCH3 | 3-CH2CH3 |
A-180 | 3-OCF3 | 3-CH2CH3 |
A-181 | 2-F | 3-Br |
A-182 | 2-Cl | 3-Br |
A-183 | 2-CH3 | 3-Br |
A-184 | 2-CF3 | 3-Br |
A-185 | 2-OCH3 | 3-Br |
A-186 | 2-OCF3 | 3-Br |
A-187 | 3-F | 3-Br |
A-188 | 3-Cl | 3-Br |
A-189 | 3-CH3 | 3-Br |
A-190 | 3-CF3 | 3-Br |
A-191 | 3-OCH3 | 3-Br |
A-192 | 3-OCF3 | 3-Br |
A-193 | 2-F | 3-Cl |
A-194 | 2-Cl | 3-Cl |
编号 | (R1)n | (R2)m |
A-195 | 2-CH3 | 3-Cl |
A-196 | 2-CF3 | 3-Cl |
A-197 | 2-OCH3 | 3-Cl |
A-198 | 2-OCF3 | 3-Cl |
A-199 | 3-F | 3-Cl |
A-200 | 3-Cl | 3-Cl |
A-201 | 3-CH3 | 3-Cl |
A-202 | 3-CF3 | 3-Cl |
A-203 | 3-OCH3 | 3-Cl |
A-204 | 3-OCF3 | 3-Cl |
A-205 | 2-F | 3-F |
A-206 | 2-Cl | 3-F |
A-207 | 2-CH3 | 3-F |
A-208 | 2-CF3 | 3-F |
A-209 | 2-OCH3 | 3-F |
A-210 | 2-OCF3 | 3-F |
A-211 | 3-F | 3-F |
A-212 | 3-Cl | 3-F |
A-213 | 3-CH3 | 3-F |
A-214 | 3-CF3 | 3-F |
A-215 | 3-OCH3 | 3-F |
A-216 | 3-OCF3 | 3-F |
A-217 | 2-F | 3-CN |
A-218 | 2-Cl | 3-CN |
A-219 | 2-CH3 | 3-CN |
A-220 | 2-CF3 | 3-CN |
A-221 | 2-OCH3 | 3-CN |
A-222 | 2-OCF3 | 3-CN |
A-223 | 3-F | 3-CN |
A-224 | 3-Cl | 3-CN |
A-225 | 3-CH3 | 3-CN |
A-226 | 3-CF3 | 3-CN |
A-227 | 3-OCH3 | 3-CN |
A-228 | 3-OCF3 | 3-CN |
A-229 | 2-F | 3-NO2 |
A-230 | 2-Cl | 3-NO2 |
A-231 | 2-CH3 | 3-NO2 |
A-232 | 2-CF3 | 3-NO2 |
A-233 | 2-OCH3 | 3-NO2 |
A-234 | 2-OCF3 | 3-NO2 |
编号 | (R1)n | (R2)m |
A-235 | 3-F | 3-NO2 |
A-236 | 3-Cl | 3-NO2 |
A-237 | 3-CH3 | 3-NO2 |
A-238 | 3-CF3 | 3-NO2 |
A-239 | 3-OCH3 | 3-NO2 |
A-240 | 3-OCF3 | 3-NO2 |
A-241 | 2-F | 3-OCH3 |
A-242 | 2-Cl | 3-OCH3 |
A-243 | 2-CH3 | 3-OCH3 |
A-244 | 2-CF3 | 3-OCH3 |
A-245 | 2-OCH3 | 3-OCH3 |
A-246 | 2-OCF3 | 3-OCH3 |
A-247 | 3-F | 3-OCH3 |
A-248 | 3-Cl | 3-OCH3 |
A-249 | 3-CH3 | 3-OCH3 |
A-250 | 3-CF3 | 3-OCH3 |
A-251 | 3-OCH3 | 3-OCH3 |
A-252 | 3-OCF3 | 3-OCH3 |
A-253 | 2-F | 3-CF3 |
A-254 | 2-Cl | 3-CF3 |
A-255 | 2-CH3 | 3-CF3 |
A-256 | 2-CF3 | 3-CF3 |
A-257 | 2-OCH3 | 3-CF3 |
A-258 | 2-OCF3 | 3-CF3 |
A-259 | 3-F | 3-CF3 |
A-260 | 3-Cl | 3-CF3 |
A-261 | 3-CH3 | 3-CF3 |
A-262 | 3-CF3 | 3-CF3 |
A-263 | 3-OCH3 | 3-CF3 |
A-264 | 3-OCF3 | 3-CF3 |
A-265 | 2-Cl | 3-OCF3 |
A-266 | 2-CH3 | 3-OCF3 |
A-267 | 2-CF3 | 3-OCF3 |
A-268 | 2-OCH3 | 3-OCF3 |
A-269 | 2-OCF3 | 3-OCF3 |
A-270 | 3-F | 3-OCF3 |
A-271 | 3-Cl | 3-OCF3 |
A-272 | 3-CH3 | 3-OCF3 |
A-273 | 3-CF3 | 3-OCF3 |
A-274 | 3-OCH3 | 3-OCF3 |
编号 | (R1)n | (R2)m |
A-275 | 3-OCF3 | 3-OCF3 |
A-276 | 2-F | 3-CF(CF3)2 |
A-277 | 2-Cl | 3-CF(CF3)2 |
A-278 | 2-CH3 | 3-CF(CF3)2 |
A-279 | 2-CF3 | 3-CF(CF3)2 |
A-280 | 2-OCH3 | 3-CF(CF3)2 |
A-281 | 2-OCF3 | 3-CF(CF3)2 |
A-282 | 3-F | 3-CF(CF3)2 |
A-283 | 3-Cl | 3-CF(CF3)2 |
A-284 | 3-CH3 | 3-CF(CF3)2 |
A-285 | 3-CF3 | 3-CF(CF3)2 |
A-286 | 3-OCH3 | 3-CF(CF3)2 |
A-287 | 3-OCF3 | 3-CF(CF3)2 |
A-288 | 2-Cl | 3-SCH3 |
A-289 | 2-CH3 | 3-SCH3 |
A-290 | 2-CF3 | 3-SCH3 |
A-291 | 2-OCH3 | 3-SCH3 |
A-292 | 2-OCF3 | 3-SCH3 |
A-293 | 3-F | 3-SCH3 |
A-294 | 3-Cl | 3-SCH3 |
A-295 | 3-CH3 | 3-SCH3 |
A-296 | 3-CF3 | 3-SCH3 |
A-297 | 3-OCH3 | 3-SCH3 |
A-298 | 3-OCF3 | 3-SCH3 |
A-299 | 2-F | 3-C(=O)CH3 |
A-300 | 2-Cl | 3-C(=O)CH3 |
A-301 | 2-CH3 | 3-C(=O)CH3 |
A-302 | 2-CF3 | 3-C(=O)CH3 |
A-303 | 2-OCH3 | 3-C(=O)CH3 |
A-304 | 2-OCF3 | 3-C(=O)CH3 |
A-305 | 3-F | 3-C(=O)CH3 |
A-306 | 3-Cl | 3-C(=O)CH3 |
A-307 | 3-CH3 | 3-C(=O)CH3 |
A-308 | 3-CF3 | 3-C(=O)CH3 |
A-309 | 3-OCH3 | 3-C(=O)CH3 |
A-310 | 3-OCF3 | 3-C(=O)CH3 |
A-311 | 2-F | 3-C(=NOCH3)CH3 |
A-312 | 2-Cl | 3-C(=NOCH3)CH3 |
A-313 | 2-CH3 | 3-C(=NOCH3)CH3 |
A-314 | 2-CF3 | 3-C(=NOCH3)CH3 |
编号 | (R1)n | (R2)m |
A-315 | 2-OCH3 | 3-C(=NOCH3)CH3 |
A-316 | 2-OCF3 | 3-C(=NOCH3)CH3 |
A-317 | 3-F | 3-C(=NOCH3)CH3 |
A-318 | 3-Cl | 3-C(=NOCH3)CH3 |
A-319 | 3-CH3 | 3-C(=NOCH3)CH3 |
A-320 | 3-CF3 | 3-C(=NOCH3)CH3 |
A-321 | 3-OCH3 | 3-C(=NOCH3)CH3 |
A-322 | 3-OCF3 | 3-C(=NOCH3)CH3 |
A-323 | 2-F | 4-CH3 |
A-324 | 2-Cl | 4-CH3 |
A-325 | 2-CH3 | 4-CH3 |
A-326 | 2-CF3 | 4-CH3 |
A-327 | 2-OCH3 | 4-CH3 |
A-328 | 2-OCF3 | 4-CH3 |
A-329 | 3-F | 4-CH3 |
A-330 | 3-Cl | 4-CH3 |
A-331 | 3-CH3 | 4-CH3 |
A-332 | 3-CF3 | 4-CH3 |
A-333 | 3-OCH3 | 4-CH3 |
A-334 | 3-OCF3 | 4-CH3 |
A-335 | 2-F | 4-CH2CH3 |
A-336 | 2-Cl | 4-CH2CH3 |
A-337 | 2-CH3 | 4-CH2CH3 |
A-338 | 2-CF3 | 4-CH2CH3 |
A-339 | 2-OCH3 | 4-CH2CH3 |
A-340 | 2-OCF3 | 4-CH2CH3 |
A-341 | 3-F | 4-CH2CH3 |
A-342 | 3-Cl | 4-CH2CH3 |
A-343 | 3-CH3 | 4-CH2CH3 |
A-344 | 3-CF3 | 4-CH2CH3 |
A-345 | 3-OCH3 | 4-CH2CH3 |
A-346 | 3-OCF3 | 4-CH2CH3 |
A-347 | 2-F | 4-Br |
A-348 | 2-Cl | 4-Br |
A-349 | 2-CH3 | 4-Br |
A-350 | 2-CF3 | 4-Br |
A-351 | 2-OCH3 | 4-Br |
A-352 | 2-OCF3 | 4-Br |
A-353 | 3-F | 4-Br |
A-354 | 3-Cl | 4-Br |
编号 | (R1)n | (R2)m |
A-355 | 3-CH3 | 4-Br |
A-356 | 3-CF3 | 4-Br |
A-357 | 3-OCH3 | 4-Br |
A-358 | 3-OCF3 | 4-Br |
A-359 | 2-F | 4-Cl |
A-360 | 2-Cl | 4-Cl |
A-361 | 2-CH3 | 4-Cl |
A-362 | 2-CF3 | 4-Cl |
A-363 | 2-OCH3 | 4-Cl |
A-364 | 2-OCF3 | 4-Cl |
A-365 | 3-F | 4-Cl |
A-366 | 3-Cl | 4-Cl |
A-367 | 3-CH3 | 4-Cl |
A-368 | 3-CF3 | 4-Cl |
A-369 | 3-OCH3 | 4-Cl |
A-370 | 3-OCF3 | 4-Cl |
A-371 | 2-F | 4-F |
A-372 | 2-Cl | 4-F |
A-373 | 2-CH3 | 4-F |
A-374 | 2-CF3 | 4-F |
A-375 | 2-OCH3 | 4-F |
A-376 | 2-OCF3 | 4-F |
A-377 | 3-F | 4-F |
A-378 | 3-Cl | 4-F |
A-379 | 3-CH3 | 4-F |
A-380 | 3-CF3 | 4-F |
A-381 | 3-OCH3 | 4-F |
A-382 | 3-OCF3 | 4-F |
A-383 | 2-F | 4-CN |
A-384 | 2-Cl | 4-CN |
A-385 | 2-CH3 | 4-CN |
A-386 | 2-CF3 | 4-CN |
A-387 | 2-OCH3 | 4-CN |
A-388 | 2-OCF3 | 4-CN |
A-389 | 3-F | 4-CN |
A-390 | 3-Cl | 4-CN |
A-391 | 3-CH3 | 4-CN |
A-392 | 3-CF3 | 4-CN |
A-393 | 3-OCH3 | 4-CN |
A-394 | 3-OCF3 | 4-CN |
编号 | (R1)n | (R2)m |
A-395 | 2-F | 4-NO2 |
A-396 | 2-Cl | 4-NO2 |
A-397 | 2-CH3 | 4-NO2 |
A-398 | 2-CF3 | 4-NO2 |
A-399 | 2-OCH3 | 4-NO2 |
A-400 | 2-OCF3 | 4-NO2 |
A-401 | 3-F | 4-NO2 |
A-402 | 3-Cl | 4-NO2 |
A-403 | 3-CH3 | 4-NO2 |
A-404 | 3-CF3 | 4-NO2 |
A-405 | 3-OCH3 | 4-NO2 |
A-406 | 3-OCF3 | 4-NO2 |
A-407 | 2-F | 4-OCH3 |
A-408 | 2-Cl | 4-OCH3 |
A-409 | 2-CH3 | 4-OCH3 |
A-410 | 2-CF3 | 4-OCH3 |
A-411 | 2-OCH3 | 4-OCH3 |
A-412 | 2-OCF3 | 4-OCH3 |
A-413 | 3-F | 4-OCH3 |
A-414 | 3-Cl | 4-OCH3 |
A-415 | 3-CH3 | 4-OCH3 |
A-416 | 3-CF3 | 4-OCH3 |
A-417 | 3-OCH3 | 4-OCH3 |
A-418 | 3-OCF3 | 4-OCH3 |
A-419 | 2-F | 4-OCH2CH3 |
A-420 | 2-Cl | 4-OCH2CH3 |
A-421 | 2-CH3 | 4-OCH2CH3 |
A-422 | 2-CF3 | 4-OCH2CH3 |
A-423 | 2-OCH3 | 4-OCH2CH3 |
A-424 | 2-OCF3 | 4-OCH2CH3 |
A-425 | 3-F | 4-OCH2CH3 |
A-426 | 3-Cl | 4-OCH2CH3 |
A-427 | 3-CH3 | 4-OCH2CH3 |
A-428 | 3-CF3 | 4-OCH2CH3 |
A-429 | 3-OCH3 | 4-OCH2CH3 |
A-430 | 3-OCF3 | 4-OCH2CH3 |
A-431 | 2-F | 4-OCH(CH3)2 |
A-432 | 2-Cl | 4-OCH(CH3)2 |
A-433 | 2-CH3 | 4-OCH(CH3)2 |
A-434 | 2-CF3 | 4-OCH(CH3)2 |
编号 | (R1)n | (R2)m |
A-435 | 2-OCH3 | 4-OCH(CH3)2 |
A-436 | 2-OCF3 | 4-OCH(CH3)2 |
A-437 | 3-F | 4-OCH(CH3)2 |
A-438 | 3-Cl | 4-OCH(CH3)2 |
A-439 | 3-CH3 | 4-OCH(CH3)2 |
A-440 | 3-CF3 | 4-OCH(CH3)2 |
A-441 | 3-OCH3 | 4-OCH(CH3)2 |
A-442 | 3-OCF3 | 4-OCH(CH3)2 |
A-443 | 2-F | 4-OC(CH3)3 |
A-444 | 2-Cl | 4-OC(CH3)3 |
A-445 | 2-CH3 | 4-OC(CH3)3 |
A-446 | 2-CF3 | 4-OC(CH3)3 |
A-447 | 2-OCH3 | 4-OC(CH3)3 |
A-448 | 2-OCF3 | 4-OC(CH3)3 |
A-449 | 3-F | 4-OC(CH3)3 |
A-450 | 3-Cl | 4-OC(CH3)3 |
A-451 | 3-CH3 | 4-OC(CH3)3 |
A-452 | 3-CF3 | 4-OC(CH3)3 |
A-453 | 3-OCH3 | 4-OC(CH3)3 |
A-454 | 3-OCF3 | 4-OC(CH3)3 |
A-455 | 2-F | 4-CF3 |
A-456 | 2-Cl | 4-CF3 |
A-457 | 2-CH3 | 4-CF3 |
A-458 | 2-CF3 | 4-CF3 |
A-459 | 2-OCH3 | 4-CF3 |
A-460 | 2-OCF3 | 4-CF3 |
A-461 | 3-F | 4-CF3 |
A-462 | 3-Cl | 4-CF3 |
A-463 | 3-CH3 | 4-CF3 |
A-464 | 3-CF3 | 4-CF3 |
A-465 | 3-OCH3 | 4-CF3 |
A-466 | 3-OCF3 | 4-CF3 |
A-467 | 2-F | 4-OCF3 |
A-468 | 2-Cl | 4-OCF3 |
A-469 | 2-CH3 | 4-OCF3 |
A-470 | 2-CF3 | 4-OCF3 |
A-471 | 2-OCH3 | 4-OCF3 |
A-472 | 2-OCF3 | 4-OCF3 |
A-473 | 3-F | 4-OCF3 |
A-474 | 3-Cl | 4-OCF3 |
编号 | (R1)n | (R2)m |
A-475 | 3-CH3 | 4-OCF3 |
A-476 | 3-CF3 | 4-OCF3 |
A-477 | 3-OCH3 | 4-OCF3 |
A-478 | 3-OCF3 | 4-OCF3 |
A-479 | 2-F | 4-SCH3 |
A-480 | 2-Cl | 4-SCH3 |
A-481 | 2-CH3 | 4-SCH3 |
A-482 | 2-CF3 | 4-SCH3 |
A-483 | 2-OCH3 | 4-SCH3 |
A-484 | 2-OCF3 | 4-SCH3 |
A-485 | 3-F | 4-SCH3 |
A-486 | 3-Cl | 4-SCH3 |
A-487 | 3-CH3 | 4-SCH3 |
A-488 | 3-CF3 | 4-SCH3 |
A-489 | 3-OCH3 | 4-SCH3 |
A-490 | 3-OCF3 | 4-SCH3 |
A-491 | 2-F | 4-C(=O)CH3 |
A-492 | 2-Cl | 4-C(=O)CH3 |
A-493 | 2-CH3 | 4-C(=O)CH3 |
A-494 | 2-CF3 | 4-C(=O)CH3 |
A-495 | 2-OCH3 | 4-C(=O)CH3 |
A-496 | 2-OCF3 | 4-C(=O)CH3 |
A-497 | 3-F | 4-C(=O)CH3 |
A-498 | 3-Cl | 4-C(=O)CH3 |
A-499 | 3-CH3 | 4-C(=O)CH3 |
A-500 | 3-CF3 | 4-C(=O)CH3 |
A-501 | 3-OCH3 | 4-C(=O)CH3 |
A-502 | 3-OCF3 | 4-C(=O)CH3 |
A-503 | 2-F | 4-C(=NOCH3)CH3 |
A-504 | 2-Cl | 4-C(=NOCH3)CH3 |
A-505 | 2-CH3 | 4-C(=NOCH3)CH3 |
A-506 | 2-CF3 | 4-C(=NOCH3)CH3 |
A-507 | 2-OCH3 | 4-C(=NOCH3)CH3 |
A-508 | 2-OCF3 | 4-C(=NOCH3)CH3 |
A-509 | 3-F | 4-C(=NOCH3)CH3 |
A-510 | 3-Cl | 4-C(=NOCH3)CH3 |
A-511 | 3-CH3 | 4-C(=NOCH3)CH3 |
A-512 | 3-CF3 | 4-C(=NOCH3)CH3 |
A-513 | 3-OCH3 | 4-C(=OCH3)CH3 |
A-514 | 3-OCF3 | 4-C(=OCH3)CH3 |
编号 | (R1)n | (R2)m |
A-515 | 2-F | 4-CF(CF3)2 |
A-516 | 2-Cl | 4-CF(CF3)2 |
A-517 | 2-CH3 | 4-CF(CF3)2 |
A-518 | 2-CF3 | 4-CF(CF3)2 |
A-519 | 2-OCH3 | 4-CF(CF3)2 |
A-520 | 2-OCF3 | 4-CF(CF3)2 |
A-521 | 3-F | 4-CF(CF3)2 |
A-522 | 3-Cl | 4-CF(CF3)2 |
A-523 | 3-CH3 | 4-CF(CF3)2 |
A-524 | 3-CF3 | 4-CF(CF3)2 |
A-525 | 3-OCH3 | 4-CF(CF3)2 |
A-526 | 3-OCF3 | 4-CF(CF3)2 |
A-527 | 2-F | 2,4-(CH3)2 |
A-528 | 2-Cl | 2,4-(CH3)2 |
A-529 | 2-CH3 | 2,4-(CH3)2 |
A-530 | 2-CF3 | 2,4-(CH3)2 |
A-531 | 2-OCH3 | 2,4-(CH3)2 |
A-532 | 2-OCF3 | 2,4-(CH3)2 |
A-533 | 3-F | 2,4-(CH3)2 |
A-534 | 3-Cl | 2,4-(CH3)2 |
A-535 | 3-CH3 | 2,4-(CH3)2 |
A-536 | 3-CF3 | 2,4-(CH3)2 |
A-537 | 3-OCH3 | 2,4-(CH3)2 |
A-538 | 3-OCF3 | 2,4-(CH3)2 |
A-539 | 2-F | 2,4-(CH2CH3)2 |
A-540 | 2-Cl | 2,4-(CH2CH3)2 |
A-541 | 2-CH3 | 2,4-(CH2CH3)2 |
A-542 | 2-CF3 | 2,4-(CH2CH3)2 |
A-543 | 2-OCH3 | 2,4-(CH2CH3)2 |
A-544 | 2-OCF3 | 2,4-(CH2CH3)2 |
A-545 | 3-F | 2,4-(CH2CH3)2 |
A-546 | 3-Cl | 2,4-(CH2CH3)2 |
A-547 | 3-CH3 | 2,4-(CH2CH3)2 |
A-548 | 3-CF3 | 2,4-(CH2CH3)2 |
A-549 | 3-OCH3 | 2,4-(CH2CH3)2 |
A-550 | 3-OCF3 | 2,4-(CH2CH3)2 |
A-551 | 2-F | 2,4-Br2 |
A-552 | 2-Cl | 2,4-Br2 |
A-553 | 2-CH3 | 2,4-Br2 |
A-554 | 2-CF3 | 2,4-Br2 |
编号 | (R1)n | (R2)m |
A-555 | 2-OCH3 | 2,4-Br2 |
A-556 | 2-OCF3 | 2,4-Br2 |
A-557 | 3-F | 2,4-Br2 |
A-558 | 3-Cl | 2,4-Br2 |
A-559 | 3-CH3 | 2,4-Br2 |
A-560 | 3-CF3 | 2,4-Br2 |
A-561 | 3-OCH3 | 2,4-Br2 |
A-562 | 3-OCF3 | 2,4-Br2 |
A-563 | 2-F | 2,4-Cl2 |
A-564 | 2-Cl | 2,4-Cl2 |
A-565 | 2-CH3 | 2,4-Cl2 |
A-566 | 2-CF3 | 2,4-Cl2 |
A-567 | 2-OCH3 | 2,4-Cl2 |
A-568 | 2-OCF3 | 2,4-Cl2 |
A-569 | 3-F | 2,4-Cl2 |
A-570 | 3-Cl | 2,4-Cl2 |
A-571 | 3-CH3 | 2,4-Cl2 |
A-572 | 3-CF3 | 2,4-Cl2 |
A-573 | 3-OCH3 | 2,4-Cl2 |
A-574 | 3-OCF3 | 2,4-Cl2 |
A-575 | 2-F | 2,4-F2 |
A-576 | 2-Cl | 2,4-F2 |
A-577 | 2-CH3 | 2,4-F2 |
A-578 | 2-CF3 | 2,4-F2 |
A-579 | 2-OCH3 | 2,4-F2 |
A-580 | 2-OCF3 | 2,4-F2 |
A-581 | 3-F | 2,4-F2 |
A-582 | 3-Cl | 2,4-F2 |
A-583 | 3-CH3 | 2,4-F2 |
A-584 | 3-CF3 | 2,4-F2 |
A-585 | 3-OCH3 | 2,4-F2 |
A-586 | 3-OCF3 | 2,4-F2 |
A-587 | 2-F | 2,4-(OCH3)2 |
A-588 | 2-Cl | 2,4-(OCH3)2 |
A-589 | 2-CH3 | 2,4-(OCH3)2 |
A-590 | 2-CF3 | 2,4-(OCH3)2 |
A-591 | 2-OCH3 | 2,4-(OCH3)2 |
A-592 | 2-OCF3 | 2,4-(OCH3)2 |
A-593 | 3-F | 2,4-(OCH3)2 |
A-594 | 3-Cl | 2,4-(OCH3)2 |
编号 | (R1)n | (R2)m |
A-595 | 3-CH3 | 2,4-(OCH3)2 |
A-596 | 3-CF3 | 2,4-(OCH3)2 |
A-597 | 3-OCH3 | 2,4-(OCH3)2 |
A-598 | 3-OCF3 | 2,4-(OCH3)2 |
A-599 | 2-F | 2,4-(CF3)2 |
A-600 | 2-Cl | 2,4-(CF3)2 |
A-601 | 2-CH3 | 2,4-(CF3)2 |
A-602 | 2-CF3 | 2,4-(CF3)2 |
A-603 | 2-OCH3 | 2,4-(CF3)2 |
A-604 | 2-OCF3 | 2,4-(CF3)2 |
A-605 | 3-F | 2,4-(CF3)2 |
A-606 | 3-Cl | 2,4-(CF3)2 |
A-607 | 3-CH3 | 2,4-(CF3)2 |
A-608 | 3-CF3 | 2,4-(CF3)2 |
A-609 | 3-OCH3 | 2,4-(CF3)2 |
A-610 | 3-OCF3 | 2,4-(CF3)2 |
A-611 | 2-F | 2,4-(OCF3)2 |
A-612 | 2-Cl | 2,4-(OCF3)2 |
A-613 | 2-CH3 | 2,4-(OCF3)2 |
A-614 | 2-CF3 | 2,4-(OCF3)2 |
A-615 | 2-OCH3 | 2,4-(OCF3)2 |
A-616 | 2-OCF3 | 2,4-(OCF3)2 |
A-617 | 3-F | 2,4-(OCF3)2 |
A-618 | 3-Cl | 2,4-(OCF3)2 |
A-619 | 3-CH3 | 2,4-(OCF3)2 |
A-620 | 3-CF3 | 2,4-(OCF3)2 |
A-621 | 3-OCH3 | 2,4-(OCF3)2 |
A-622 | 3-OCF3 | 2,4-(OCF3)2 |
A-623 | 2-F | 2,5-(CH3)2 |
A-624 | 2-Cl | 2,5-(CH3)2 |
A-625 | 2-CH3 | 2,5-(CH3)2 |
A-626 | 2-CF3 | 2,5-(CH3)2 |
A-627 | 2-OCH3 | 2,5-(CH3)2 |
A-628 | 2-OCF3 | 2,5-(CH3)2 |
A-629 | 3-F | 2,5-(CH3)2 |
A-630 | 3-Cl | 2,5-(CH3)2 |
A-631 | 3-CH3 | 2,5-(CH3)2 |
A-632 | 3-CF3 | 2,5-(CH3)2 |
A-633 | 3-OCH3 | 2,5-(CH3)2 |
A-634 | 3-OCF3 | 2,5-(CH3)2 |
编号 | (R1)n | (R2)m |
A-635 | 2-F | 2,5-Cl2 |
A-636 | 2-Cl | 2,5-Cl2 |
A-637 | 2-CH3 | 2,5-Cl2 |
A-638 | 2-CF3 | 2,5-Cl2 |
A-639 | 2-OCH3 | 2,5-Cl2 |
A-640 | 2-OCF3 | 2,5-Cl2 |
A-641 | 3-F | 2,5-Cl2 |
A-642 | 3-Cl | 2,5-Cl2 |
A-643 | 3-CH3 | 2,5-Cl2 |
A-644 | 3-CF3 | 2,5-Cl2 |
A-645 | 3-OCH3 | 2,5-Cl2 |
A-646 | 3-OCF3 | 2,5-Cl2 |
A-647 | 2-F | 2,5-F2 |
A-648 | 2-Cl | 2,5-F2 |
A-649 | 2-CH3 | 2,5-F2 |
A-650 | 2-CF3 | 2,5-F2 |
A-651 | 2-OCH3 | 2,5-F2 |
A-652 | 2-OCF3 | 2,5-F2 |
A-653 | 3-F | 2,5-F2 |
A-654 | 3-Cl | 2,5-F2 |
A-655 | 3-CH3 | 2,5-F2 |
A-656 | 3-CF3 | 2,5-F2 |
A-657 | 3-OCH3 | 2,5-F2 |
A-658 | 3-OCF3 | 2,5-F2 |
A-659 | 2-F | 2,5-(OCH3)2 |
A-660 | 2-Cl | 2,5-(OCH3)2 |
A-661 | 2-CH3 | 2,5-(OCH3)2 |
A-662 | 2-CF3 | 2,5-(OCH3)2 |
A-663 | 2-OCH3 | 2,5-(OCH3)2 |
A-664 | 2-OCF3 | 2,5-(OCH3)2 |
A-665 | 3-F | 2,5-(OCH3)2 |
A-666 | 3-Cl | 2,5-(OCH3)2 |
A-667 | 3-CH3 | 2,5-(OCH3)2 |
A-668 | 3-CF3 | 2,5-(OCH3)2 |
A-669 | 3-OCH3 | 2,5-(OCH3)2 |
A-670 | 3-OCF3 | 2,5-(OCH3)2 |
A-671 | 2-F | 2,5-(CF3)2 |
A-672 | 2-Cl | 2,5-(CF3)2 |
A-673 | 2-CH3 | 2,5-(CF3)2 |
A-674 | 2-CF3 | 2,5-(CF3)2 |
编号 | (R1)n | (R2)m |
A-675 | 2-OCH3 | 2,5-(CF3)2 |
A-676 | 2-OCF3 | 2,5-(CF3)2 |
A-677 | 3-F | 2,5-(CF3)2 |
A-678 | 3-Cl | 2,5-(CF3)2 |
A-679 | 3-CH3 | 2,5-(CF3)2 |
A-680 | 3-CF3 | 2,5-(CF3)2 |
A-681 | 3-OCH3 | 2,5-(CF3)2 |
A-682 | 3-OCF3 | 2,5-(CF3)2 |
A-683 | 2-F | 2,5-(OCF3)2 |
A-684 | 2-Cl | 2,5-(OCF3)2 |
A-685 | 2-CH3 | 2,5-(OCF3)2 |
A-686 | 2-CF3 | 2,5-(OCF3)2 |
A-687 | 2-OCH3 | 2,5-(OCF3)2 |
A-688 | 2-OCF3 | 2,5-(OCF3)2 |
A-689 | 3-F | 2,5-(OCF3)2 |
A-690 | 3-Cl | 2,5-(OCF3)2 |
A-691 | 3-CH3 | 2,5-(OCF3)2 |
A-692 | 3-CF3 | 2,5-(OCF3)2 |
A-693 | 3-OCH3 | 2,5-(OCF3)2 |
A-694 | 3-OCF3 | 2,5-(OCF3)2 |
A-695 | 2-F | 2,5-(SCH3)2 |
A-696 | 2-Cl | 2,5-(SCH3)2 |
A-697 | 2-CH3 | 2,5-(SCH3)2 |
A-698 | 2-CF3 | 2,5-(SCH3)2 |
A-699 | 2-OCH3 | 2,5-(SCH3)2 |
A-700 | 2-OCF3 | 2,5-(SCH3)2 |
A-701 | 3-F | 2,5-(SCH3)2 |
A-702 | 3-Cl | 2,5-(SCH3)2 |
A-703 | 3-CH3 | 2,5-(SCH3)2 |
A-704 | 3-CF3 | 2,5-(SCH3)2 |
A-705 | 3-OCH3 | 2,5-(SCH3)2 |
A-706 | 3-OCF3 | 2,5-(SCH3)2 |
A-707 | 2-F | 2,6-(CH3)2 |
A-708 | 2-Cl | 2,6-(CH3)2 |
A-709 | 2-CH3 | 2,6-(CH3)2 |
A-710 | 2-CF3 | 2,6-(CH3)2 |
A-711 | 2-OCH3 | 2,6-(CH3)2 |
A-712 | 2-OCF3 | 2,6-(CH3)2 |
A-713 | 3-F | 2,6-(CH3)2 |
A-714 | 3-Cl | 2,6-(CH3)2 |
编号 | (R1)n | (R2)m |
A-715 | 3-CH3 | 2,6-(CH3)2 |
A-716 | 3-CF3 | 2,6-(CH3)2 |
A-717 | 3-OCH3 | 2,6-(CH3)2 |
A-718 | 3-OCF3 | 2,6-(CH3)2 |
A-719 | 2-F | 3,5-(CH3)2 |
A-720 | 2-Cl | 3,5-(CH3)2 |
A-721 | 2-CH3 | 3,5-(CH3)2 |
A-722 | 2-CF3 | 3,5-(CH3)2 |
A-723 | 2-OCH3 | 3,5-(CH3)2 |
A-724 | 2-OCF3 | 3,5-(CH3)2 |
A-725 | 3-F | 3,5-(CH3)2 |
A-726 | 3-Cl | 3,5-(CH3)2 |
A-727 | 3-CH3 | 3,5-(CH3)2 |
A-728 | 3-CF3 | 3,5-(CH3)2 |
A-729 | 3-OCH3 | 3,5-(CH3)2 |
A-730 | 3-OCF3 | 3,5-(CH3)2 |
A-731 | 2-F | 3,5-(CF3)2 |
A-732 | 2-Cl | 3,5-(CF3)2 |
A-733 | 2-CH3 | 3,5-(CF3)2 |
A-734 | 2-CF3 | 3,5-(CF3)2 |
A-735 | 2-OCH3 | 3,5-(CF3)2 |
A-736 | 2-OCF3 | 3,5-(CF3)2 |
A-737 | 3-F | 3,5-(CF3)2 |
A-738 | 3-Cl | 3,5-(CF3)2 |
A-739 | 3-CH3 | 3,5-(CF3)2 |
A-740 | 3-CF3 | 3,5-(CF3)2 |
A-741 | 3-OCH3 | 3,5-(CF3)2 |
A-742 | 3-OCF3 | 3,5-(CF3)2 |
A-743 | 2-F | 3,5-(OCF3)2 |
A-744 | 2-Cl | 3,5-(OCF3)2 |
A-745 | 2-CH3 | 3,5-(OCF3)2 |
A-746 | 2-CF3 | 3,5-(OCF3)2 |
A-747 | 2-OCH3 | 3,5-(OCF3)2 |
A-748 | 2-OCF3 | 3,5-(OCF3)2 |
A-749 | 3-F | 3,5-(OCF3)2 |
A-750 | 3-Cl | 3,5-(OCF3)2 |
A-751 | 3-CH3 | 3,5-(OCF3)2 |
A-752 | 3-CF3 | 3,5-(OCF3)2 |
A-753 | 3-OCH3 | 3,5-(OCF3)2 |
A-754 | 3-OCF3 | 3,5-(OCF3)2 |
编号 | (R1)n | (R2)m |
A-755 | 2-F | 3-Cl,4-F |
A-756 | 2-Cl | 3-Cl,4-F |
A-757 | 2-CH3 | 3-Cl,4-F |
A-758 | 2-CF3 | 3-Cl,4-F |
A-759 | 2-OCH3 | 3-Cl,4-F |
A-760 | 2-OCF3 | 3-Cl,4-F |
A-761 | 3-F | 3-C1,4-F |
A-762 | 3-Cl | 3-Cl,4-F |
A-763 | 3-CH3 | 3-Cl,4-F |
A-764 | 3-CF3 | 3-Cl,4-F |
A-765 | 3-OCH3 | 3-Cl,4-F |
A-766 | 3-OCF3 | 3-Cl,4-F |
A-767 | 2-F | 3-CH3,4-F |
A-768 | 2-Cl | 3-CH3,4-F |
A-769 | 2-CH3 | 3-CH3,4-F |
A-770 | 2-CF3 | 3-CH3,4-F |
A-771 | 2-OCH3 | 3-CH3,4-F |
A-772 | 2-OCF3 | 3-CH3,4-F |
A-773 | 3-F | 3-CH3,4-F |
A-774 | 3-Cl | 3-CH3,4-F |
A-775 | 3-CH3 | 3-CH3,4-F |
A-776 | 3-CF3 | 3-CH3,4-F |
A-777 | 3-OCH3 | 3-CH3,4-F |
A-778 | 3-OCF3 | 3-CH3,4-F |
A-779 | 2-F | 2-C1,4-F |
A-780 | 2-Cl | 2-Cl,4-F |
A-781 | 2-CH3 | 2-Cl,4-F |
A-782 | 2-CF3 | 2-Cl,4-F |
A-783 | 2-OCH3 | 2-Cl,4-F |
A-784 | 2-OCF3 | 2-C1,4-F |
A-785 | 3-F | 2-Cl,4-F |
A-786 | 3-Cl | 2-Cl,4-F |
A-787 | 3-CH3 | 2-Cl,4-F |
A-788 | 3-CF3 | 2-Cl,4-F |
A-789 | 3-OCH3 | 2-Cl,4-F |
A-790 | 3-OCF3 | 2-Cl,4-F |
A-791 | 2-F | 2-Cl,4-OCH3 |
A-792 | 2-Cl | 2-Cl,4-OCH3 |
A-793 | 2-CH3 | 2-Cl,4-OCH3 |
A-794 | 2-CF3 | 2-Cl,4-OCH3 |
编号 | (R1)n | (R2)m |
A-795 | 2-OCH3 | 2-Cl,4-OCH3 |
A-796 | 2-OCF3 | 2-Cl,4-OCH3 |
A-797 | 3-F | 2-Cl,4-OCH3 |
A-798 | 3-Cl | 2-Cl,4-OCH3 |
A-799 | 3-CH3 | 2-Cl,4-OCH3 |
A-800 | 3-CF3 | 2-Cl,4-OCH3 |
A-801 | 3-OCH3 | 2-Cl,4-OCH3 |
A-802 | 3-OCF3 | 2-Cl,4-OCH3 |
A-803 | 2-F | 2-Cl,4-CF(CF3)2 |
A-804 | 2-Cl | 2-Cl,4-CF(CF3)2 |
A-805 | 2-CH3 | 2-Cl,4-CF(CF3)2 |
A-806 | 2-CF3 | 2-Cl,4-CF(CF3)2 |
A-807 | 2-OCH3 | 2-Cl,4-CF(CF3)2 |
A-808 | 2-OCF3 | 2-Cl,4-CF(CF3)2 |
A-809 | 3-F | 2-Cl,4-CF(CF3)2 |
A-810 | 3-Cl | 2-Cl,4-CF(CF3)2 |
A-811 | 3-CH3 | 2-Cl,4-CF(CF3)2 |
A-812 | 3-CF3 | 2-Cl,4-CF(CF3)2 |
A-813 | 3-OCH3 | 2-Cl,4-CF(CF3)2 |
A-814 | 3-OCF3 | 2-Cl,4-CF(CF3)2 |
A-815 | 2-F | 2-F,4-Cl |
A-816 | 2-Cl | 2-F,4-Cl |
A-817 | 2-CH3 | 2-F,4-Cl |
A-818 | 2-CF3 | 2-F,4-Cl |
A-819 | 2-OCH3 | 2-F,4-Cl |
A-820 | 2-OCF3 | 2-F,4-Cl |
A-821 | 3-F | 2-F,4-Cl |
A-822 | 3-Cl | 2-F,4-Cl |
A-823 | 3-CH3 | 2-F,4-Cl |
A-824 | 3-CF3 | 2-F,4-Cl |
A-825 | 3-OCH3 | 2-F,4-Cl |
A-826 | 3-OCF3 | 2-F,4-Cl |
A-827 | 2-F | 2-F,4-Br |
A-828 | 2-Cl | 2-F,4-Br |
A-829 | 2-CH3 | 2-F,4-Br |
A-830 | 2-CF3 | 2-F,4-Br |
A-831 | 2-OCH3 | 2-F,4-Br |
A-832 | 2-OCF3 | 2-F,4-Br |
A-833 | 3-F | 2-F,4-Br |
A-834 | 3-Cl | 2-F,4-Br |
编号 | (R1)n | (R2)m |
A-835 | 3-CH3 | 2-F,4-Br |
A-836 | 3-CF3 | 2-F,4-Br |
A-837 | 3-OCH3 | 2-F,4-Br |
A-838 | 3-OCF3 | 2-F,4-Br |
A-839 | 2-F | 2-F,4-CH3 |
A-840 | 2-Cl | 2-F,4-CH3 |
A-841 | 2-CH3 | 2-F,4-CH3 |
A-842 | 2-CF3 | 2-F,4-CH3 |
A-843 | 2-OCH3 | 2-F,4-CH3 |
A-844 | 2-OCF3 | 2-F,4-CH3 |
A-845 | 3-F | 2-F,4-CH3 |
A-846 | 3-Cl | 2-F,4-CH3 |
A-847 | 3-CH3 | 2-F,4-CH3 |
A-848 | 3-CF3 | 2-F,4-CH3 |
A-849 | 3-OCH3 | 2-F,4-CH3 |
A-850 | 3-OCF3 | 2-F,4-CH3 |
A-851 | 2-F | 2-F,4-CF3 |
A-852 | 2-Cl | 2-F,4-CF3 |
A-853 | 2-CH3 | 2-F,4-CF3 |
A-854 | 2-CF3 | 2-F,4-CF3 |
A-855 | 2-OCH3 | 2-F,4-CF3 |
A-856 | 2-OCF3 | 2-F,4-CF3 |
A-857 | 3-F | 2-F,4-CF3 |
A-858 | 3-Cl | 2-F,4-CF3 |
A-859 | 3-CH3 | 2-F,4-CF3 |
A-860 | 3-CF3 | 2-F,4-CF3 |
A-861 | 3-OCH3 | 2-F,4-CF3 |
A-862 | 3-OCF3 | 2-F,4-CF3 |
A-863 | 2-F | 2-F,4-OCH3 |
A-864 | 2-Cl | 2-F,4-OCH3 |
A-865 | 2-CH3 | 2-F,4-OCH3 |
A-866 | 2-CF3 | 2-F,4-OCH3 |
A-867 | 2-OCH3 | 2-F,4-OCH3 |
A-868 | 2-OCF3 | 2-F,4-OCH3 |
A-869 | 3-F | 2-F,4-OCH3 |
A-870 | 3-Cl | 2-F,4-OCH3 |
A-871 | 3-CH3 | 2-F,4-OCH3 |
A-872 | 3-CF3 | 2-F,4-OCH3 |
A-873 | 3-OCH3 | 2-F,4-OCH3 |
A-874 | 3-OCF3 | 2-F,4-OCH3 |
编号 | (R1)n | (R2)m |
A-875 | 2-Cl | 2-F,4-CF(CF3)2 |
A-876 | 2-CH3 | 2-F,4-CF(CF3)2 |
A-877 | 2-CF3 | 2-F,4-CF(CF3)2 |
A-878 | 2-OCH3 | 2-F,4-CF(CF3)2 |
A-879 | 2-OCF3 | 2-F,4-CF(CF3)2 |
A-880 | 3-F | 2-F,4-CF(CF3)2 |
A-881 | 3-Cl | 2-F,4-CF(CF3)2 |
A-882 | 3-CH3 | 2-F,4-CF(CF3)2 |
A-883 | 3-CF3 | 2-F,4-CF(CF3)2 |
A-884 | 3-OCH3 | 2-F,4-CF(CF3)2 |
A-885 | 3-OCF3 | 2-F,4-CF(CF3)2 |
A-886 | 2-F | 2-CH3,4-OCH3 |
A-887 | 2-Cl | 2-CH3,4-OCH3 |
A-888 | 2-CH3 | 2-CH3,4-OCH3 |
A-889 | 2-CF3 | 2-CH3,4-OCH3 |
A-890 | 2-OCH3 | 2-CH3,4-OCH3 |
A-891 | 2-OCF3 | 2-CH3,4-OCH3 |
A-892 | 3-F | 2-CH3,4-OCH3 |
A-893 | 3-Cl | 2-CH3,4-OCH3 |
A-894 | 3-CH3 | 2-CH3,4-OCH3 |
A-895 | 3-CF3 | 2-CH3,4-OCH3 |
A-896 | 3-OCH3 | 2-CH3,4-OCH3 |
A-897 | 3-OCF3 | 2-CH3,4-OCH3 |
A-898 | 2-F | 2-CH3,4-Cl |
A-899 | 2-Cl | 2-CH3,4-Cl |
A-900 | 2-CH3 | 2-CH3,4-Cl |
A-901 | 2-CF3 | 2-CH3,4-Cl |
A-902 | 2-OCH3 | 2-CH3,4-Cl |
A-903 | 2-OCF3 | 2-CH3,4-Cl |
A-904 | 3-F | 2-CH3,4-Cl |
A-905 | 3-Cl | 2-CH3,4-Cl |
A-906 | 3-CH3 | 2-CH3,4-Cl |
A-907 | 3-CF3 | 2-CH3,4-Cl |
A-908 | 3-OCH3 | 2-CH3,4-Cl |
A-909 | 3-OCF3 | 2-CH3,4-Cl |
A-910 | 2-F | 2-CH3,4-F |
A-911 | 2-Cl | 2-CH3,4-F |
A-912 | 2-CH3 | 2-CH3,4-F |
A-913 | 2-CF3 | 2-CH3,4-F |
A-914 | 2-OCH3 | 2-CH3,4-F |
编号 | (R1)n | (R2)m |
A-915 | 2-OCF3 | 2-CH3,4-F |
A-916 | 3-F | 2-CH3,4-F |
A-917 | 3-Cl | 2-CH3,4-F |
A-918 | 3-CH3 | 2-CH3,4-F |
A-919 | 3-CF3 | 2-CH3,4-F |
A-920 | 3-OCH3 | 2-CH3,4-F |
A-921 | 3-OCF3 | 2-CH3,4-F |
A-922 | 2-F | 2-CH3,4-CF3 |
A-923 | 2-Cl | 2-CH3,4-CF3 |
A-924 | 2-CH3 | 2-CH3,4-CF3 |
A-925 | 2-CF3 | 2-CH3,4-CF3 |
A-926 | 2-OCH3 | 2-CH3,4-CF3 |
A-927 | 2-OCF3 | 2-CH3,4-CF3 |
A-928 | 3-F | 2-CH3,4-CF3 |
A-929 | 3-Cl | 2-CH3,4-CF3 |
A-930 | 3-CH3 | 2-CH3,4-CF3 |
A-931 | 3-CF3 | 2-CH3,4-CF3 |
A-932 | 3-OCH3 | 2-CH3,4-CF3 |
A-933 | 3-OCF3 | 2-CH3,4-CF3 |
A-934 | 2-F | 2-CH3,4-CF(CF3)2 |
A-935 | 2-Cl | 2-CH3,4-CF(CF3)2 |
A-936 | 2-CH3 | 2-CH3,4-CF(CF3)2 |
A-937 | 2-CF3 | 2-CH3,4-CF(CF3)2 |
A-938 | 2-OCH3 | 2-CH3,4-CF(CF3)2 |
A-939 | 2-OCF3 | 2-CH3,4-CF(CF3)2 |
A-940 | 3-F | 2-CH3,4-CF(CF3)2 |
A-941 | 3-Cl | 2-CH3,4-CF(CF3)2 |
A-942 | 3-CH3 | 2-CH3,4-CF(CF3)2 |
A-943 | 3-CF3 | 2-CH3,4-CF(CF3)2 |
A-944 | 3-OCH3 | 2-CH3,4-CF(CF3)2 |
A-945 | 3-OCF3 | 2-CH3,4-CF(CF3)2 |
A-946 | 2-F | 2-OCH3,4-F |
A-947 | 2-Cl | 2-OCH3,4-F |
A-948 | 2-CH3 | 2-OCH3,4-F |
A-949 | 2-CF3 | 2-OCH3,4-F |
A-950 | 2-OCH3 | 2-OCH3,4-F |
A-951 | 2-OCF3 | 2-OCH3,4-F |
A-952 | 3-F | 2-OCH3,4-F |
A-953 | 3-Cl | 2-OCH3,4-F |
A-954 | 3-CH3 | 2-OCH3,4-F |
编号 | (R1)n | (R2)m |
A-955 | 3-CF3 | 2-OCH3,4-F |
A-956 | 3-OCH3 | 2-OCH3,4-F |
A-957 | 3-OCF3 | 2-OCH3,4-F |
A-958 | 2-F | 2-OCH3,4-Cl |
A-959 | 2-Cl | 2-OCH3,4-Cl |
A-960 | 2-CH3 | 2-OCH3,4-Cl |
A-961 | 2-CF3 | 2-OCH3,4-Cl |
A-962 | 2-OCH3 | 2-OCH3,4-Cl |
A-963 | 2-OCF3 | 2-OCH3,4-Cl |
A-964 | 3-F | 2-OCH3,4-Cl |
A-965 | 3-Cl | 2-OCH3,4-Cl |
A-966 | 3-CH3 | 2-OCH3,4-Cl |
A-967 | 3-CF3 | 2-OCH3,4-Cl |
A-968 | 3-OCH3 | 2-OCH3,4-Cl |
A-969 | 3-OCF3 | 2-OCH3,4-Cl |
A-970 | 2-F | 3-NO2,4-CH3 |
A-971 | 2-Cl | 3-NO2,4-CH3 |
A-972 | 2-CH3 | 3-NO2,4-CH3 |
A-973 | 2-CF3 | 3-NO2,4-CH3 |
A-974 | 2-OCH3 | 3-NO2,4-CH3 |
A-975 | 2-OCF3 | 3-NO2,4-CH3 |
A-976 | 3-F | 3-NO2,4-CH3 |
A-977 | 3-Cl | 3-NO2,4-CH3 |
A-978 | 3-CH3 | 3-NO2,4-CH3 |
A-979 | 3-CF3 | 3-NO2,4-CH3 |
A-980 | 3-OCH3 | 3-NO2,4-CH3 |
A-981 | 3-OCF3 | 3-NO2,4-CH3 |
A-982 | 3-F | 2-CF3,4-Cl |
A-983 | 3-Cl | 2-CF3,4-Cl |
A-984 | 3-CH3 | 2-CF3,4-Cl |
A-985 | 3-CF3 | 2-CF3,4-Cl |
A-986 | 3-OCH3 | 2-CF3,4-Cl |
A-987 | 3-OCF3 | 2-CF3,4-Cl |
A-988 | 3-F | 2-Cl,4-CF3 |
A-989 | 3-Cl | 2-Cl,4-CF3 |
A-990 | 3-CH3 | 2-Cl,4-CF3 |
A-991 | 3-CF3 | 2-Cl,4-CF3 |
A-992 | 3-OCH3 | 2-Cl,4-CF3 |
A-993 | 3-OCF3 | 2-Cl,4-CF3 |
A-994 | 3-F | 2-CF3,4-OCH3 |
编号 | (R1)n | (R2)m |
A-995 | 3-Cl | 2-CF3,4-OCH3 |
A-996 | 3-CH3 | 2-CF3,4-OCH3 |
A-997 | 3-CF3 | 2-CF3,4-OCH3 |
A-998 | 3-OCH3 | 2-CF3,4-OCH3 |
A-999 | 3-OCF3 | 2-CF3,4-OCH3 |
A-1000 | 3-F | 3-Cl,4-CF3 |
A-1001 | 3-Cl | 3-Cl,4-CF3 |
A-1002 | 3-CH3 | 3-Cl,4-CF3 |
A-1003 | 3-CF3 | 3-Cl,4-CF3 |
A-1004 | 3-OCH3 | 3-Cl,4-CF3 |
A-1005 | 3-OCF3 | 3-Cl,4-CF3 |
A-1006 | 3-F | 2-CF3,5-F |
A-1007 | 3-Cl | 2-CF3,5-F |
A-1008 | 3-CH3 | 2-CF3,5-F |
A-1009 | 3-CF3 | 2-CF3,5-F |
A-1010 | 3-OCH3 | 2-CF3,5-F |
A-1011 | 3-OCF3 | 2-CF3,5-F |
A-1012 | 3-F | 2-CF3,5-Cl |
A-1013 | 3-Cl | 2-CF3,5-Cl |
A-1014 | 3-CH3 | 2-CF3,5-Cl |
A-1015 | 3-CF3 | 2-CF3,5-Cl |
A-1016 | 3-OCH3 | 2-CF3,5-Cl |
A-1017 | 3-OCF3 | 2-CF3,5-Cl |
A-1018 | 3-F | 2-Cl,5-CF3 |
A-1019 | 3-Cl | 2-Cl,5-CF3 |
A-1020 | 3-CH3 | 2-Cl,5-CF3 |
A-1021 | 3-CF3 | 2-Cl,5-CF3 |
A-1022 | 3-OCH3 | 2-Cl,5-CF3 |
A-1023 | 3-OCF3 | 2-Cl,5-CF3 |
A-1024 | 3-F | 2-F,5-CF3 |
A-1025 | 3-Cl | 2-F,5-CF3 |
A-1026 | 3-CH3 | 2-F,5-CF3 |
A-1027 | 3-CF3 | 2-F,5-CF3 |
A-1028 | 3-OCH3 | 2-F,5-CF3 |
A-1029 | 3-OCF3 | 2-F,5-CF3 |
A-1030 | 3-F | 3-F,4-CF3 |
A-1031 | 3-Cl | 3-F,4-CF3 |
A-1032 | 3-CH3 | 3-F,4-CF3 |
A-1033 | 3-CF3 | 3-F,4-CF3 |
A-1034 | 3-OCH3 | 3-F,4-CF3 |
编号 | (R1)n | (R2)m |
A-1035 | 3-OCF3 | 3-F,4-CF3 |
A-1036 | 3-F | 3-Cl,4-CF3 |
A-1037 | 3-Cl | 3-Cl,4-CF3 |
A-1038 | 3-CH3 | 3-Cl,4-CF3 |
A-1039 | 3-CF3 | 3-Cl,4-CF3 |
A-1040 | 3-OCH3 | 3-Cl,4-CF3 |
A-1041 | 3-OCF3 | 3-Cl,4-CF3 |
A-1042 | 3-F | 3-Cl,4-Cl |
A-1043 | 3-Cl | 3-Cl,4-Cl |
A-1044 | 3-CH3 | 3-Cl,4-Cl |
A-1045 | 3-CF3 | 3-Cl,4-Cl |
A-1046 | 3-OCH3 | 3-Cl,4-Cl |
A-1047 | 3-OCF3 | 3-Cl,4-Cl |
A-1048 | 3-F | 3-F,4-Cl |
A-1049 | 3-Cl | 3-F,4-Cl |
A-1050 | 3-CH3 | 3-F,4-Cl |
A-1051 | 3-CF3 | 3-F,4-Cl |
A-1052 | 3-OCH3 | 3-F,4-Cl |
A-1053 | 3-OCF3 | 3-F,4-Cl |
A-1054 | 3-F | 3-CF3,4-Cl |
A-1055 | 3-Cl | 3-CF3,4-Cl |
A-1056 | 3-CH3 | 3-CF3,4-Cl |
A-1057 | 3-CF3 | 3-CF3,4-Cl |
A-1058 | 3-OCH3 | 3-CF3,4-Cl |
A-1059 | 3-OCF3 | 3-CF3,4-Cl |
表2
其中Q表示Q-2且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表3
其中Q表示Q-3且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表4
其中Q表示Q-4且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表5
其中Q表示Q-5且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表6
其中Q表示Q-6且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表7
其中Q表示Q-7且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表8
其中Q表示Q-8且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表9
其中Q表示Q-9且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表10
其中Q表示Q-10且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表11
其中Q表示Q-11且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表12
其中Q表示Q-12且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表13
其中Q表示Q-13且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表14
其中Q表示Q-14且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表15
其中Q表示Q-15且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表16
其中Q表示Q-16且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表17
其中Q表示Q-17且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表18
其中Q表示Q-18且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表19
其中Q表示Q-19且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表20
其中Q表示Q-20且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表21
其中Q表示Q-21且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表22
其中Q表示Q-22且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表23
其中Q表示Q-23且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表24
其中Q表示Q-24且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表25
其中Q表示Q-25且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表26
其中Q表示Q-26且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表27
其中Q表示Q-27且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表28
其中Q表示Q-28且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表29
其中Q表示Q-29且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表30
其中Q表示Q-30且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表31
其中Q表示Q-31且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表32
其中Q表示Q-32且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表33
其中Q表示Q-33且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表34
其中Q表示Q-34且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表35
其中Q表示Q-35且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表36
其中Q表示Q-36且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表37
其中Q表示Q-37且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表38
其中Q表示Q-38且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表39
其中Q表示Q-39且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表40
其中Q表示Q-40且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表41
其中Q表示Q-41且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表42
其中Q表示Q-42且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表43
其中Q表示Q-43且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表44
其中Q表示Q-44且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表45
其中Q表示Q-45且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表46
其中Q表示Q-46且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表47
其中Q表示Q-47且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表48
其中Q表示Q-48且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表49
其中Q表示Q-49且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表50
其中Q表示Q-50且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表51
其中Q表示Q-51且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表52
其中Q表示Q-52且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表53
其中Q表示Q-53且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表54
其中Q表示Q-54且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
表55
其中Q表示Q-55且(R1)n和(R2)m的结合在每种情况下对应于表B的一行的式(I.A)化合物
本发明的式(I)化合物可以类似于对于制备联苯基化合物本身已知的现有技术方法通过各种途径制备。有利的是可以如方案1和2所述得到它们。
通常而言,式(I)的喹啉化合物可以通过式(II)化合物与式(III)的硼酸衍生物通过方案1所示的Suzuki偶联进行反应而制备。
方案1:
在方案1中,R1、R2、R3、R4、R5、R6、n和m如上所定义,Ri和Rj各自独立地为氢或C1-C4烷基,或者Ri和Rj一起形成1,2-亚乙基或1,2-亚丙基结构部分,该结构部分的碳原子可以未被取代或可以全部或部分被甲基取代,以及L2为合适的离去基团。
合适的离去基团L2为卤素,优选氯、溴或碘,烷基羧酸酯、苯甲酸酯、烷基磺酸酯、卤代烷基磺酸酯或芳基磺酸酯,最优选氯或溴。
该反应通常在碱和催化剂,尤其是钯催化剂存在下进行,所述催化剂例如在下列文献中描述:Synth.Commun.,第11卷,第513页(1981);Acc.Chem.Res.,第15卷,第178-184页(1982);Chem.Rev.,第95卷,第2457-2483页(1995);Organic Letters,第6卷(16),第2808页(2004);“金属催化的交叉偶联反应”,第2版,Wiley,VCH 2005(编辑De Meijere,Diederich);“用于有机合成的有机钯化学手册”(编辑Negishi),Wiley,Interscience,New York,2002;“官能化有机金属化合物手册”(编辑P.Knochel),Wiley,VCH,2005。
合适的催化剂是四(三苯基膦)钯(0);二(三苯基膦)氯化钯(II);二(乙腈)氯化钯(II);[1,1’-二(二苯基膦基)二茂铁]氯化钯(II)/二氯甲烷(1∶1)配合物;二[二(1,2-二苯基膦基)乙烷]钯(0);二(二(1,2-二苯基膦基)丁烷)氯化钯(II);乙酸钯(II);氯化钯(II)和乙酸钯(II)/三-邻甲苯基膦配合物或膦与Pd盐的混合物或膦与Pd配合物的混合物如二亚苄基丙酮-钯和三叔丁基膦(或其四氟硼酸盐)、三环己基膦的混合物;或聚合物结合的Pd-三苯基膦催化剂体系。
合适的碱通常为无机化合物,如碱金属和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钠、碳酸钾、碳酸铯和碳酸钙,还有碱金属碳酸氢盐,如碳酸氢钠,碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾和叔丁醇钾,此外还有有机碱,例如叔胺,如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶,如可力丁、卢剔啶和4-二甲氨基吡啶,以及双环胺。特别优选诸如碳酸钠、碳酸钾、碳酸铯、三乙胺和碳酸氢钠的碱。
相对于1mol化合物(II),碱以1∶1-1∶10,优选1∶1.5-5的摩尔比使用;相对于1mol化合物(II),硼酸以1∶1-1∶5,优选1∶1-1∶2.5的摩尔比使用。在某些情况下,对于易于提纯可能是有利的是相对于1mol化合物(II)以0.7∶1-0.99∶1的不足化学计算量使用硼酸。
该反应通常在惰性有机溶剂中进行。合适的溶剂是脂族烃,如戊烷、己烷、环己烷和石油醚,芳族烃,如甲苯、邻二甲苯、间二甲苯和对二甲苯,醚类,如二异丙基醚、叔丁基甲基醚、二噁烷、茴香醚和四氢呋喃以及二甲氧基乙烷,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,还有二甲亚砜、二甲基甲酰胺和二甲基乙酰胺,特别优选醚类,如四氢呋喃、二噁烷和二甲氧基乙烷。还可以使用所述溶剂的混合物或与水的混合物。
该反应通常在20-180℃,优选40-120℃的温度下进行。
在反应完成之后,式(I)化合物可以通过使用常规方法如将反应混合物加入水中、用有机溶剂萃取、浓缩萃取液等而分离。需要的话,分离的化合物(I)可以通过诸如层析、再结晶等的技术提纯。
还可以向反应混合物中加入清除剂以通过与副产物或未反应的原料结合并简单过滤而除去它们。详情请见“Synthesis and purification catalog”,Argonaut,2003和其中所引用的文献。
硼酸或酯(III)可市购或者可以根据“Science of Synthesis”,第6卷,Thieme,2005;WO 02/042275;Synlett 2003,(8),第1204页;J.Org.Chem.,2003,68,第3729页,Synthesis,2000,第442页,J.Org.Chem.,1995,60,第750页或“官能化有机金属化合物手册”(编辑P.Knochel),Wiley,VCH,2005制备。
化合物(II)可以如方案2所示通过磺酰氯(IV)与喹啉(V)的反应得到。
方案2
在方案2中,L2、R1、R2、R3、R4、R5、R6、n和m如上所定义且L1为离去基团如羟基或卤素,优选氯。
磺酰氯(IV)与喹啉(V)的反应可以按照有机化学中的标准方法进行,例如参见Lieb.Ann.Chem.,第641页,1990或WO 2005/033081。
该反应通常在惰性有机溶剂中进行。合适的溶剂是脂族烃,如戊烷、己烷、环己烷和石油醚,芳族烃,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃,如二氯甲烷、氯仿和氯苯,醚类,如乙醚、二异丙基醚、叔丁基甲基醚、二噁烷、茴香醚和四氢呋喃,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,还有二甲亚砜、二甲基甲酰胺和二甲基乙酰胺,优选四氢呋喃、甲基叔丁基醚、二氯甲烷、氯仿、乙腈、甲苯或二甲基甲酰胺。还可以使用所述溶剂的混合物。
可能有利的是在碱存在下进行该反应。合适的碱通常为无机化合物,如碱金属和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钠、碳酸钾和碳酸钙,还有碱金属碳酸氢盐,如碳酸氢钠,此外还有有机碱,例如叔胺,如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶,如可力丁、卢剔啶和4-二甲氨基吡啶,以及双环胺。特别优选吡啶、三乙胺和碳酸钾。碱通常以等摩尔量、过量使用或合适的话用作溶剂。碱的过量相对于1mol化合物(V)通常为0.5-5摩尔当量。
该反应通常在-30℃至120℃,优选-10℃至100℃的温度下进行。
原料通常以等摩尔量相互反应。
若磺酰氯(IV)不可市购,则可以根据现有技术已知的程序得到它们。
喹啉(V)由文献已知或可市购(例如4-亚甲基氨基喹啉:CAS-Nr5632-13-3;6-氯-4-亚甲基氨基喹啉:CAS-Nr 859814-05-5;6-甲氧基-4-亚甲基氨基喹啉:CAS-Nr 708261-71-6;8-羟基-4-亚甲基氨基喹啉:CAS-Nr33976-91-9;6-甲氧基-8-氯-4-亚甲基氨基喹啉:CAS-Nr 857207-07-9),或者它们可以由其中X如在下列方案中所定义的喹啉前体(VI)通过还原而制备:
还原方法可以在文献中找到,例如在Houben-Weyl,Band 10/4,Thieme,Stuttgart,1968;Band 11/2,1957;Band E5,1985;J.Heterocycl.Chem.,1997,34(6),第1661-1667页;J.Chem.Soc.1954,第1165页;Heterocycles,41(4),第675-688页,1995;J.Org.Chem.,1982,47,第3153页;Heterocycles,1996,43(9),第1893-1900页;J.Prakt.Chem-Chem.Ztg.336(8),第695-697页,1994中找到;或者对本领域熟练技术人员是已知的。
肟(VIa)可以由相应的醛(X=CHO;化合物(VId))或甲基衍生物(X=CH3;化合物(VIe))制备,如Houben-Weyl,Band 10/4,Thieme,Stuttgart,1968;Band 11/2,1957;Band E5,1985;J.Prakt.Chem-Chem.Ztg.336(8),第695-697页,1994;Tetrahedron Lett.42(39),第6815-6818页,2001;或Heterocycles,29(9),第1741-1760页,1989所述。
醛(VId)可市购(例如6-氯-4-喹啉甲醛、7-甲氧基-4-喹啉甲醛、喹啉-4-甲醛)或者可以如J.Org.Chem.51(4),第536-537页,1986所述由4-甲基喹啉合成或如Eur.J.Org.Chem.,2003(8),第1576-1588页;TetrahedronLett.1999,40(19),第3719-3722页;Tetrahedron,1999,55(41),第12149-12156页所示由卤代衍生物(X=卤素,化合物(VIf))合成。
甲基衍生物(VIe)可市购(例如6-氯-4-甲基喹啉;6,8-二甲氧基喹啉)或者可以根据“Science of Synthesis”,第15卷,Thieme,Stuttgart,2005合成。
腈(VIb)可以通过在有或无额外催化剂下与氰化物源反应而由相应的卤素衍生物(VIf)(X=卤素,优选氯、溴或碘)制备,例如如Tetrahedron Lett.42(38),第6707-6710页,2001;Chem.Eur.J.,2003,9(8),第1828-1836页;Chem.Commun.(Cambridge),2004(12),第1388-1389页;J.Organomet.Chem.2004,689(24),第4576-4583页或J.Chem.Soc.Perk.T.,1(16),第2323-2326页,1999所述。或者,可以如“Synthesis”,Stuttgart(10),第943-944,1992或其中所引用的文献或Heterocycl.Chem.1997,34(6),第1661-1667页所述使酰胺或肟脱水得到相应的腈(VIb)。
4-卤代喹啉(VIf)或者可市购或者可以根据“Science of Synthesis”,第15卷,Thieme,Stuttgart,2005或例如根据下列文献或其中的引用文献合成:4-氯-6,7-二甲氧基喹啉:Journal Med.Chem.48(5),第1359页,2005;4-氯-5,7-二氯喹啉:Indian,187817,2002年6月29日;4-氯-7-氯喹啉:Tetrahedron,60(13),第3017页,2004;4-氯-7-三氟甲基喹啉:Tetrahedronlett.,31(8),第1093页,1990;4-氯-7,8-二甲氧基喹啉:Tetrahedron,41(15),第3033页,1985;4-氯-8-甲氧基喹啉:Chem.Berichte 118(4),第1556页,1985;4-氯-(6或7或8)-碘喹啉、4-溴-(6或7或8)-碘喹啉、4-碘-(6或7或8)-碘喹啉:J.Med.Chem.,21(3),第268页,1978。
构建合适前体或改变取代方式的其他方法可以在“Synthesis”,Stuttgart(1),第31-32页,1993;Tetrahedron,1993,49(24),第5315-5326页;“Methods in Science of Synthesis”,Band 15及其中所引用的文献;Bioorg.Med.Chem.Lett.1997,7(23),第2935-2940页;J.Am.Chem.Soc.,1946,68,第1264页或Org.Synth.1955,III,第272页中找到。
N-氧化物可以根据常规氧化方法由化合物(I)制备,例如通过用有机过酸如间氯过苯甲酸[Journal of Medicinal Chemistry,38(11),1892-1903(1995);WO 03/64572]或无机氧化剂如过氧化氢[参见Jounal ofHeterocyclic Chemistry,18(7),1305-8(1981)]或过硫酸氢钾制剂[参见Journal of the American Chemical Society,123(25),5962-5973(2001)]处理化合物(I)。
在某些情况下,就后处理或提纯容易性而言可能有利的是不分离化合物(V)而在一个罐中进行化合物(VI)到化合物(V)的还原和胺(V)与化合物(IV)的反应。
某些式(II)的中间体是新的。这些也为本发明主题。
尤其是式(II.1)的中间体为本发明主题:
其中
L2为氯、溴或碘,和
n、R1、R3、R4、R5和R6具有上面对式(I)化合物所给的含义,尤其是作为优选给出的含义。
若各化合物(I)不能通过上述途径得到,则可以通过衍生其他化合物(I)或通过所述合成途径的常规改变而制备它们。
式(I)化合物的制备可能导致它们以异构体混合物(立体异构体、对映体)得到。需要的话,可以通过常用于此的方法如结晶或也在旋光活性吸附物上的层析将它们拆分,得到纯异构体。
由于它们的优异活性,通式(I)的化合物及其N-氧化物和盐可以用于防治选自有害昆虫、蜘蛛和线虫的动物害虫。
因此,本发明进一步涉及一种用于防治这类动物害虫的农用组合物,包含杀虫有效量的至少一种通式(I)的化合物、其N-氧化物或可农用盐和至少一种惰性液体和/或固体可农用载体以及需要的话至少一种表面活性剂。
该组合物可以含有单一的式(I)活性化合物、其N-氧化物或可农用盐,或几种本发明的活性式(I)化合物、其N-氧化物或可农用盐的混合物。
式(I)化合物及其N-氧化物或可农用盐以及包含它们的杀虫组合物是防治节肢动物害虫和线虫的有效试剂。由式(I)化合物防治的动物害虫例如包括:
鳞翅目昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)、木棉虫(Alabama argillacea)、黎豆夜蛾(Anticarsiagemmatalis)、Argyresthia conjugella、叉纹夜蛾(Autographa gamma)、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、二化螟(Cirphis unipuncta)、苹果小卷蛾(Cydiapomonella)、松毛虫(Dendrolimus pini)、Diaphania nitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、Evetriabouliana、Feltia subterranea、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothiszea)、菜螟(Hellula undalis)、Hibernia defoliaria、美国白蛾(Hyphantriacunea)、苹果巢蛾(Hyponomeuta malinellus)、番茄虫蛾(Keiferialycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygma exigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucoptera scitella)、Lithocolletisblancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostegesticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、黄杉毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinianubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophoragossypiella)、疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutellaxylostella)、大豆夜蛾(Pseudoplusia includens)、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(Sitotroga cerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、草地夜蛾(Spodoptera frugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoeapityocampa、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)和Zeiraphera canadensis;
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallussolstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum)、甜菜隐食甲(Atomaria linearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchusrufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotomatrifurcata、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、Conoderusvespertinus、石刁柏负泥虫(Crioceris asparagi)、长角叶甲(Diabroticalongicornis)、Diabrotica 12-punctata、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ips typographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lemamelanopus)、马铃薯叶甲(Leptinotarsa decemlineata)、Limoniuscalifornicus、稻水象甲(Lissorhoptrus oryzophilus)、Melanotus communis、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchus ovatus)、辣根猿叶甲(Phaedon cochleariae)、Phyllotreta chrysocephala、食叶鳃金龟属(Phyllophaga)、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata)、日本金龟子(Popillia j aponica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilus gran aria);双翅目昆虫(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、剌扰伊蚊(Aedes vexans)、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anophelesmaculipennis)、地中海实蝇(Ceratitis capitata)、蛆症金蝇(Chrysomyabezziana)、Chrysomya hominivorax、Chrysomya macellaria、高粱瘿蚊(Contarinia sorghicola)、Cordylobia anthropophaga、尖音库蚊(Culexpipiens)、瓜蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、小毛厕蝇(Fannia canicularis)、马蝇(Gasterophilusintestinalis)、刺舌蝇(Glossina morsitans)、Haematobia irritans、Haplodiplosis equestris、花生田灰地种蝇(Hylemyia platura)、纹皮蝇(Hypoderma lineata)、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、麦瘿蚊(Mayetiola destructor)、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、Phorbiaantiqua、萝卜蝇(Phorbia brassicae)、Phorbia coarctata、樱桃实蝇(Rhagoletis cerasi)、苹果实蝇(Rhagoletis pomonella)、Tabanus bovinus、Tipula oleracea和欧洲大蚊(Tipula paludosa);
蓟马(缨翅目(Thysanoptera)),例如兰花蓟马(Dichromothrips corbetti)、烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)、桔硬蓟马(Scirtothrips citri)、稻蓟马(Thrips oryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci),膜翅目昆虫(膜翅目(Hymenoptera)),例如新疆菜叶蜂(Athalia rosae)、切叶蚁(Atta cephalotes)、Atta sexdens、Atta texana、Hoplocampaminuta、Hoplocampa testudinea、小黄家蚁(Monomorium pharaonis)、热带火蚁(Solenopsis geminate)和红火蚁(Solenopsis invicta),异翅目昆虫(异翅目(Heteroptera),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercus cingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygasterintegriceps)、烟草蝽(Euschistus impictiventris)、棉红铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lyguspratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubea insularis和Thyanta perditor;
同翅目昆虫(同翅目(Homoptera)),例如Acyrthosiphon onobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphis grossulariae)、Aphis schneideri、卷叶蚜(Aphis spiraecola)、Aphis sambuci、豌豆蚜(Acyrthosiphon pisum)、马铃薯蚜(Aulacorthumsolani)、银叶粉虱(Bemisia argentifolii)、Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycaudus persicae、Brachycaudusprunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosiphagossypii、Chaetosiphon fragaefolii、Cryptomyzus ribis、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphis radicola)、Dysaulacorthum pseudosolani、Dysaphisplantaginea、Dysaphis pyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphumavenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphonrosae)、Megoura viciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophium dirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzusascalonicus)、Myzus cerasi、桃蚜(Myzus persicae)、李瘤蚜(Myzus varians)、Nasonovia ribis-nigri、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigusbursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodonhumuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphum maidis)、禾谷溢管蚜(Rhopalosiphum padi)、Rhopalosiphum insertum、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneuralanuginosa、麦长管蚜(Sitobion avenae)、白背飞虱(Sogatella furcifera)、白粉虱(Trialeurodes vaporariorum)、Toxoptera aurantiiand和葡萄根瘤蚜(Viteus vitifolii);
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermesflavipes、黄肢散白蚁(Reticulitermes flavipes)、欧洲散白蚁(Reticulitermeslucifugus)和Termes natalensis,
直翅目昆虫(直翅目(Orthoptera)),例如居屋艾蟋(Acheta domestica)、东方蜚蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、欧洲球螋(Forficula auricularia)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locustamigratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplusfemur-rubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲蟑螂(Periplaneta americana)、美洲沙漠蝗(Schistocerca americana)、Schistocerca peregrina、Stauronotusmaroccanus和庭疾灶螽(Tachycines asynamorus),蜘蛛纲(Arachnoidea),如蜘蛛(蜱螨目(Acarina)),例如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae),如长星形壁虱(Amblyomma americanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argas persicus)、牛壁虱(Boophilus annulatus)、Boophilusdecoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、Ornithodorus moubata、Otobius megnini、鸡皮刺螨(Dermanyssusgallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),瘿螨属(Eriophyidae),如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨属(Tarsonemidae),如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨属(Tenuipalpidae),如紫红短须螨(Brevipalpus phoenicis);叶螨属(Tetranychidae),如朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychus citri)和oligonychus pratensis;
蚤目(Siphonaptera),例如印鼠客蚤(Xenopsylla cheopis)、角叶属(Ceratophyllus);
组合物和式(I)化合物可以用于防治线虫,尤其是植物寄生线虫如根结线虫,北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyneincognita)、爪哇根结线虫(Meloidogyne javanica)和其他根结线虫属(Meloidogyne);形成胞囊的线虫,马铃薯金线虫(Globodera rostochiensis)和其他球胞囊属(Globodera);禾谷胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、三叶草胞囊线虫(Heterodera trifolii)和其他胞囊线虫属(Heterodera);种子肿瘿线虫,粒线虫属(Anguina);茎叶线虫,滑刃线虫属(Aphelenchoides);刺线虫,杂草刺线虫(Belonolaimus longicaudatus)和其他针刺线虫属(Belonolaimus);松线虫,松材线虫(Bursaphelenchus xylophilus)和其他伞滑刃线虫属(Bursaphelenchus);环形线虫,环纹线虫属(Criconema)、小环线虫属(Criconemella)、轮线虫属(Criconemoides)、中环线虫属(Mesocriconema);球茎线虫,腐烂茎线虫(Ditylenchus destructor)、甘薯茎线虫(Ditylenchus dipsaci)和其他茎线虫属(Ditylenchus);锥线虫,锥线虫属(Dolichodorus);螺旋形线虫,Heliocotylenchus multicinctus和其他Helicotylenchus属;鞘线虫和鞘形(sheathoid)线虫,鞘线虫属(Hemicycliophora)和Hemicriconemoides属;Hirshmanniella属;冠线虫,Hoploaimus属;伪根结线虫,珍珠线虫属(Nacobbus);针线虫,Longidoruselongatus和其他长针线虫属(Longidorus);鞘线虫,针线虫属(Paratylenchus);根腐线虫,Pratylenchus neglectus、穿刺根腐线虫(Pratylenchus penetrans)、Pratylenchus curvitatus、Pratylenchus goodeyi和其他根腐线虫属(Pratylenchus);穿孔线虫,香蕉穿孔线虫(Radopholussimilis)和其他穿孔线虫属(Radopholus);肾形线虫,Rotylenchus robustus和其他盘旋线虫属(Rotylenchus);Scutellonema属;残根线虫,Trichodorusprimitivus和其他毛刺线虫属(Trichodorus)、拟毛刺属(Paratrichodorus);阻长线虫,Tylenchorhynchus claytoni、Tylenchorhynchus dubius和其他矮化线虫属(Tylenchorhynchus);柑桔线虫,垫刃线虫属(Tylenchulus);剑线虫,剑线虫属(Xiphinema);以及其他植物寄生线虫属。
在本发明的优选实施方案中,式(I)化合物、其N-氧化物或其可农用盐用于防治节肢动物如昆虫或蜘蛛,尤其是鳞翅目、鞘翅目和同翅目昆虫以及蜱螨目蜘蛛。本发明式(I)化合物特别可以用于防治缨翅目和同翅目昆虫。
式(I)化合物、其N-氧化物、可农用盐或包含它们的杀虫组合物可以通过使植物/作物与杀虫有效量的式(I)化合物接触而用于保护生长中的植物和作物免受动物害虫,尤其是昆虫、螨或蜘蛛的侵袭或侵染。术语“作物”指生长和收获的作物二者。
可以将式(I)化合物、其N-氧化物及其可农用盐转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。使用形式取决于特定的意欲目的;在每种情况下意欲确保本发明化合物精细且均匀地分布。
配制剂以已知方式制备(综述例如参见US 3,060,084,EP-A 707 445(对于液体浓缩物),Browning,“Agglomeration”,Chemical Engineering,1967年12月4日,147-48,Perry’s Chemical Engineer’s Handbook,第4版,McGraw-Hill,New York,1963,第8-57页及随后各页,WO 91/13546,US 4,172,714,US 4,144,050,US 3,920,442,US 5,180,587,US 5,232,701,US 5,208,030,GB 2,095,558,US 3,299,566,Klingman,Weed Control asa Science,John Wiley and Sons,Inc.,New York,1961,Hance等,WeedControl Handbook,第8版,Blackwell Scientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation technology,Wiley VCHVerlag GmbH,Weinheim(德国),2001,2.D.A.Knowles,Chemistry andTechnology of Agrochemical Formulations,Kluwer Academic Publishers,Dordrecht,1998(ISBN 0-7515-0443-8),例如通过使活性化合物与适于配制农业化学品的助剂如溶剂和/或载体,需要的话还有乳化剂、表面活性剂和分散剂、防腐剂、消泡剂、防冻剂、对于种子处理配制剂还有任选的着色剂和/或粘合剂和/或胶凝剂混合。
合适的溶剂实例是水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(N-甲基吡咯烷酮[NMP]、N-辛基吡咯烷酮[NOP])、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
合适的乳化剂是非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)。
分散剂的实例是木素亚硫酸盐废液和甲基纤维素。
所用的合适表面活性剂是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘与甲醛的缩合物和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备可直接喷雾的溶液、乳液、糊或油分散体的物质为中至高沸点的矿物油馏分如煤油或柴油,还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物,甲醇,乙醇,丙醇,丁醇,环己醇,环己酮,异佛尔酮,强极性溶剂如二甲亚砜、N-甲基吡咯烷酮和水。
还可以向配制剂中加入防冻剂如甘油、乙二醇、丙二醇和杀菌剂。
合适的消泡剂例如为基于硅的消泡剂或硬脂酸镁。
合适的防腐剂例如为二氯芬。
种子处理配制剂可以额外包含粘合剂和任选着色剂。
可以加入粘合剂以改善处理后活性材料在种子上的粘附。合适的粘合剂是嵌段共聚物EO/PO表面活性剂,还有聚乙烯醇、聚乙烯基吡咯烷酮、聚丙烯酸酯、聚甲基丙烯酸酯、聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺、聚乙烯亚胺聚醚、聚氨酯、聚乙酸乙烯酯、纤基乙酸钠和衍生于这些聚合物的共聚物。
任选还可以在配制剂中包含着色剂。对种子处理配制剂合适的着色剂或染料是若丹明B,C.I.颜料红112、C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红112、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。
胶凝剂的实例是角叉菜
粉末、撒播用材料和可撒粉产品可以通过将活性物质与固体载体混合或一起研磨来制备。
颗粒如涂敷颗粒、浸渍颗粒和均质颗粒可以通过使活性化合物与固体载体粘附而制备。
固体载体实例为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素,以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性化合物。活性化合物以90-100%,优选95-100%的纯度(根据NMR谱)使用。
对于种子处理,各配制剂可以稀释2-10倍,从而使即用制剂中的浓度为0.01-60重量%,优选0.1-40重量%活性化合物。
式(I)化合物、其N-氧化物及其可农用盐可以直接、以其配制剂形式或由其制备的使用形式(如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;意欲在每种情况下确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而,还可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
活性化合物在即用制剂中的浓度可以在较宽范围内变化。它们通常为0.0001-10重量%,优选0.01-1重量%。
活性化合物还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性化合物的配制剂或甚至可以在没有添加剂的情况下施用活性化合物。
下列为配制剂实例:
1.用水稀释的叶面施用产品。对于种子处理,该类产品可以经稀释或不经稀释而施用于种子上。
A)水溶性浓缩物(SL、LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解,从而得到活性化合物含量为10重量%的配制剂。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体,从而得到活性化合物含量为20重量%的配制剂。
C)乳油(EC)
将15重量份活性化合物溶于7重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液,从而得到活性化合物含量为15重量%的配制剂。
D)乳液(EW、EO、ES)
将40重量份活性化合物溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(例如Ultraturrax)将该混合物引入30重量份水中并制成均相乳液。用水稀释得到乳液,从而得到活性化合物含量为25重量%的配制剂。
E)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂、湿润剂和70重量份水或有机溶剂,得到细碎活性成分悬浮液。用水稀释得到稳定的活性化合物悬浮液,从而得到活性化合物含量为20重量%的配制剂。
F)水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液,从而得到活性化合物含量为50重量%的配制剂。
G)水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液,从而得到活性化合物含量为75重量%的配制剂。
H)凝胶配制剂(GF)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂、1重量份胶凝剂湿润剂和70重量份水或有机溶剂,得到细碎活性成分悬浮液。用水稀释得到稳定的活性化合物悬浮液,从而得到活性化合物含量为20重量%的配制剂。
2.不经稀释而施用的叶面施用产品。对于种子处理,该类产品可以经稀释或不经稀释而施用于种子上。
I)可撒粉粉末(DP、DS)
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到活性化合物含量为5重量%的可撒粉产品。
J)颗粒(GR、FG、GG、MG)
将0.5重量份活性化合物细碎研磨并结合95.5重量份载体,从而得到活性化合物含量为0.5重量%的配制剂。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的叶面施用颗粒。
K)ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到含有10重量%活性化合物的不经稀释而施用的叶面施用产品。
式(I)化合物还适于处理种子。常规种子处理配制剂例如包括可流动浓缩物FS、溶液LS、干处理用粉末DS、淤浆处理用水分散性粉末WS、水溶性粉末SS以及乳液ES和EC和凝胶配制剂GF。这些配制剂可以经稀释或不经稀释而施用于种子上。对种子的施用在播种之前进行,或者直接对种子进行或者在种子预萌发之后进行。
在优选实施方案中,将FS配制剂用于种子处理。通常而言,FS配制剂可以包含1-800g/l活性成分,1-200g/l表面活性剂,0-200g/l防冻剂,0-400g/l粘合剂,0-200g/l颜料和至多1L溶剂,优选水。
用于种子处理的式(I)化合物的其他优选FS配制剂包含0.5-80重量%活性成分,0.05-5重量%水,0.5-15重量%分散剂,0.1-5重量%增稠剂,5-20重量%防冻剂,0.1-2重量%消泡剂,1-20重量%颜料和/或染料,0-15重量%粘合剂/粘附剂,0-75重量%填料/赋形剂和0.01-1重量%防腐剂。
可以向活性成分中加入各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其他农药或杀菌剂,合适的话恰在紧临使用之前加入(桶混合)。这些试剂通常以1∶10-10∶1的重量比与本发明试剂混合。
式(I)化合物、其N-氧化物及其可农用盐通过接触(经由土壤、玻璃、墙壁、蚊帐、地毯、植物部分或动物部分)和摄取(诱饵或植物部分)而有效。
为了用于对抗蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀或蟑螂,优选将式(I)化合物、其N-氧化物及其可农用盐用于诱饵组合物中。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。固体诱饵可以形成适合相应应用的各种形状和形式,例如颗粒、块、棒、盘。液体诱饵可以填充到各种装置中以确保适当施用,例如敞开容器、喷雾装置、液滴源或蒸发源。凝胶可以基于含水或油状基质且可以根据粘性、水分保留或老化特性方面的特殊要求配制。
用于组合物中的诱饵是具有足够的吸引力以刺激诸如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀等的昆虫或蟑螂食用它的产品。该吸引力可以通过使用进食刺激剂或性信息素调节。食物刺激剂例如非穷举地选自动物和/或植物蛋白质(肉-、鱼-或血液膳食,昆虫部分、蛋黄)、动物和/或植物来源的脂肪和油或单-、低聚-或聚有机糖类,尤其是蔗糖、乳糖、果糖、右旋糖、葡萄糖、淀粉、果胶或甚至糖蜜或蜂蜜。水果、作物、植物、动物、昆虫的新鲜或腐败部分或其特定部分也可以用作进食刺激剂。已知性信息素更具昆虫特异性。特殊信息素描述于文献中并且对本领域熟练技术人员是已知的。
式(I)化合物、其N-氧化物及其可农用盐的配制剂如气雾剂(例如在喷雾罐中)、油喷雾剂或泵喷雾剂高度适于非专业使用者来防治害虫如蝇、跳蚤、蜱、蚊子或蟑螂。气雾剂配方优选由如下组分组成:活性化合物;溶剂如低级醇(例如甲醇、乙醇、丙醇、丁醇),酮类(例如丙酮、甲基乙基酮),沸程为约50-250℃的链烷烃(例如煤油),二甲基甲酰胺,N-甲基吡咯烷酮,二甲亚砜(DMSO),芳族烃类如甲苯、二甲苯,水;此外还有助剂,例如乳化剂如山梨糖醇单油酸酯、具有3-7mol氧化乙烯的油基乙氧基化物、脂肪醇乙氧基化物,芳香油如精油,中等脂肪酸与低级醇的酯,芳族羰基化合物;合适的话还有稳定剂如苯甲酸钠,两性表面活性剂,低级环氧化物,原甲酸三乙酯和需要的话推进剂如丙烷、丁烷、氮气、压缩空气、二甲醚、二氧化碳、氧化亚氮或这些气体的混合物。
油喷雾配制剂与气雾剂配方的不同在于没有使用推进剂。
式(I)化合物、其N-氧化物及其可农用盐以及相应的组合物还可以用于蚊香片和熏蒸片,发烟盒、蒸发器板或长效蒸发器以及扑蛾纸、扑蛾垫或其他与热无关的蒸发器体系中。
用式(I)化合物、其N-氧化物及其可农用盐及其相应的组合物控制由昆虫传递的传染性疾病(例如疟疾、登革热和黄热病,淋巴丝虫病以及利什曼病)的方法也包括处理棚屋和房子的表面、空气喷雾和浸渍窗帘、帐篷、衣物、蚊帐、采采蝇捕捉器等。施用于纤维、织物、编织物、无纺织物、网状材料或箔以及篷布上的杀虫组合物优选包含包含杀虫剂、任选的驱除剂和至少一种粘合剂的混合物。合适的驱除剂例如为N,N-二乙基-间甲苯甲酰胺(DEET),N,N-二乙基苯基乙酰胺(DEPA),1-(3-环己烷-1-基羰基)-2-甲基哌啶,(2-羟基甲基环己基)乙酸内酯,2-乙基-1,3-己二醇,避蚊酮,甲基新癸酰胺(MNDA),未用于昆虫控制的拟除虫菊酯如{(+/-)-3-烯丙基-2-甲基-4-氧代环戊-2-(+)-烯基-(+)-反式-菊酸酯(Esbiothrin),衍生于植物提取物或与植物提取物相同的驱除剂如1,8-萜二烯、丁子香酚、(+)-Eucamalol(1)、(-)-1-表-eucamalol,或来自诸如花皮桉(Eucalyptusmaculata)、蔓荆(Vitex rotundifolia)、Cymbopogan martinii、香茅(Cymbopogan citratus)(柠檬草)、亚香茅(Cymopogan nartdus)(香茅)的植物的粗植物提取物。合适的粘合剂例如选自如下单体的聚合物和共聚物:脂族酸的乙烯基酯(如乙酸乙烯酯和支链烷烃脂肪酸(versatic)乙烯基酯),醇的丙烯酸和甲基丙烯酸酯,如丙烯酸丁酯、丙烯酸2-乙基己基酯和丙烯酸甲酯,单烯属和二烯属不饱和烃,如苯乙烯,以及脂族二烯,如丁二烯。
窗帘和蚊帐的浸渍通常通过将织物材料浸入杀虫剂的乳液或分散体中或将它们喷雾于所述材料上而进行。
式(I)化合物、其N-氧化物或可兽用盐尤其还适于防治动物中和动物上的寄生虫。
因此,本发明的目的还在于提供在动物中和动物上防治寄生虫的新方法。本发明的另一目的是为动物提供更安全的杀虫剂。本发明的另一目的是进一步对动物提供可以比现有杀虫剂更低的剂量使用的杀虫剂。本发明的另一目的是对动物提供能够对寄生虫提供长残留防治的杀虫剂。
本发明还涉及用于在动物中和动物上防治寄生虫的组合物,包含杀寄生虫有效量的式(I)化合物、其N-氧化物或可兽用盐和可接受载体。
本发明还涉及一种处理、防治、预防和保护动物免受寄生虫侵袭或侵染的方法,包括口服、局部或肠胃外给予或施用杀寄生虫有效量的式(I)化合物、其N-氧化物或可兽用盐或包含它的组合物。
本发明还涉及一种制备用于处理、防治、预防或保护动物免受寄生虫侵袭或侵染的组合物的方法,该组合物包含杀寄生虫有效量的式(I)化合物、其N-氧化物或可兽用盐或包含它的组合物。
化合物对抗农业害虫的活性并不暗示着它们适于在例如在口服施用的情形下要求非催吐性低剂量、与动物的代谢相容性、低毒性和安全处理的动物中和动物上防治体内和体外寄生虫。
惊人的是现已发现式(I)化合物、其N-氧化物和可兽用盐适合防治动物中和动物上的体内和体外寄生虫。
式(I)化合物、其N-氧化物或其可兽用盐以及包含它们的组合物优选用于在包括温血动物(包括人)在内的动物和鱼中防治和预防侵袭和侵染。它们例如适于在哺乳动物如牛、绵羊、猪猡、骆驼、鹿、马、猪、家禽、兔、山羊、狗和猫,水牛、驴、黇鹿和驯鹿,以及产皮动物如水貂、灰鼠和浣熊,禽类如母鸡、鹅、火鸡和鸭以及鱼类如淡水鱼和咸水鱼如鲑鱼、鲤鱼和美洲鳗中防治和预防侵袭和侵染。
式(I)化合物、其N-氧化物或可兽用盐以及包含它们的组合物优选用于在家养动物如狗或猫中防治和预防侵袭和侵染。
在温血动物和鱼类中的侵袭包括但不限于虱、咬虱、蜱、羊鼻蝇蛆、羊蜱蝇、螯蝇、家蝇、蝇、myiasitic蝇幼虫、恙螨、蚋、蚊和蚤。
式(I)化合物、其N-氧化物或可兽用盐和包含它们的组合物适于内吸和/或非内吸控制体外和/或体内寄生虫。它们对所有或部分发育阶段有效。
式(I)化合物、其N-氧化物或可兽用盐尤其可以用于防治体外寄生虫。
式(I)化合物、其N-氧化物或可兽用盐尤其可以用于防治下列目和属的寄生虫:
蚤(蚤目),例如猫蚤(Ctenocephalides felis)、狗蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulex irritans)、穿皮潜蚤(Tungapenetrans)和具带病蚤(Nosopsyllus fasciatus),
蟑螂(蜚蠊目(Blattaria)-Blattodea),例如德国小蠊(Blattella germanica)、Blattella asahinae、美洲蟑螂(Periplaneta americana)、日本大蠊(Periplaneta j aponica)、棕色蜚蠊(Periplaneta brunnea)、Periplanetafuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blattaorientalis),
苍蝇、蚊子(双翅目),例如埃及伊蚊、白纹伊蚊(Aedes albopictus)、刺扰伊蚊、墨西哥果蝇、五斑按蚊、Anopheles crucians、白足按蚊(Anophelesalbimanus)、疟蚊(Anopheles Gambiae)、Anopheles freeborni、白踝按蚊(Anopheles leucosphyrus)、微小按蚊(Anopheles minimus)、四斑按蚊(Anopheles quadrimaculatus)、红头丽蝇(Calliphora vicina)、蛆症金蝇、Chrysomya hominivorax、Chrysomya macellaria、鹿蝇(Chrysops discalis)、Chrysops silacea、Chrysops atlanticus、Cochliomyia hominivorax、Cordylobia anthropophaga、Culicoides furens、尖音库蚊、斑蚊(Culexnigripalpus)、致倦库蚊(Culex quinquefasciatus)、媒斑蚊(Culex tarsalis)、Culiseta inornata、Culiseta melanura、Dermatobia hominis、小毛厕蝇、马蝇、刺舌蝇、须舌蝇(Glossina palpalis)、Glossina fuscipes、Glossinatachinoides、Haematobia irritans、Haplodiplosis equestris、Hippelates属、纹皮蝇、Leptoconops torrens、Lucilia caprina、铜绿蝇、丝光绿蝇、Lycoriapectoralis、沼蚊属(Mansonia)、家蝇、厩腐蝇、羊狂蝇、Phlebotomusargentipes、Psorophora columbiae、Psorophora discolor、Prosimuliummixtum、红尾肉蝇(Sarcophaga haemorrhoidalis)、肉蝇属(Sarcophaga)、Simulium vittatum、厩螫蝇(Stomoxys calcitrans)、牛虻(Tabanus bovinus)、Tabanus atratus、红色原虻(Tabanus lineola)和Tabanus similis,虱(毛虱目(Phthiraptera)),例如Pediculus humanus capitis、Pediculushumanus corporis、阴虱(Pthirus pubis)、Haematopinus eurysternus、Haematopinus suis、Linognathus vituli、Bovicola bovis、Menopon gallinae、Menacanthus stramineus和Solenopotes capillatus,
壁虱和寄生螨(寄螨目(Parasitiformes)):壁虱(蜱亚目(Ixodida)),例如黑脚硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclu s)、太平洋硬蜱(Ixodespacificus)、棕色犬壁虱(Rhiphicephalus sanguineus)、安氏革螨(Dermacentor andersoni)、美洲大革螨(Dermacentor variabilis)、长星形壁虱(Amblyomma americanum)、Ambryomma maculatum、Ornithodorushermsi、Ornithodorus turicata以及寄生螨(甲螨亚目(Mesostigmata)),例如柏氏禽刺螨(Ornithonyssus bacoti)和鸡皮刺螨(Dermanyssus gallinae);
辐螨亚目(Actinedida)(前气门亚目(Prostigmata))和粉螨亚目(Acaridida)(无气门目(Astigmata)),例如Acarapis属、Cheyletiella属、Ornithocheyletia属、鼠螨属(Myobia)、Psorergates属、蠕形螨属(Demodex)、恙螨属(Trombicula)、Listrophorus属、粉螨属(Acarus)、食酪螨属(Tyrophagus)、嗜木螨属(Caloglyphus)、Hypodectes属、Pterolichus属、痒螨属(Psoroptes)、疥螨属(Chorioptes)、耳痒螨属(Otodectes)、Sarcoptes属、背肛螨属(Notoedres)、膝螨属(Knemidocoptes)、Cytodites属和Laminosioptes属;
臭虫(Heteropterida):温带臭虫(Cimex lectularius)、热带臭虫(Cimexhemipterus)、Reduvius senilis、锥蝽属(Triatoma)、锥蝽属(Rhodnius)、Panstrongylus属和Arilus critatus,
虱目(Anoplurida),例如Haematopinus属、Linognathus属、Pediculus属、Phtirus属和Solenopotes属;
食毛目(Mallophagida)(Arnblycerina和Ischnocerina亚目),例如Trimenopon属、Menopon属、Trinoton属、Bovicola属、Werneckiella属、Lepikentron属、Trichodectes属和Felicola属;
蛔虫(Nematoda):
金针虫和Trichinosis(毛管目(Trichosyringida)),例如毛形科(Trichinellidae)(毛形属(Trichinella))、毛首科(Trichuridae)、Trichuris属、毛细线虫属(Capillaria);
杆形目(Rhabditida),例如小杆线虫属(Rhabditis)、Strongyloides属、Helicephalobus属;
圆线虫目(Strongylida),例如Strongylus属、Ancylostoma属、美洲钩虫(Necator americanus)、Bunostomum属(钩虫)、毛圆线虫属(Trichostrongylus)、捻转血矛线虫(Haemonchus contortus)、Ostertagia属、Cooperia属、细颈线虫属(Nematodirus)、Dictyocaulus属、Cyathostoma属、结节线虫属(Oesophagostomum)、猪肾虫(Stephanurus dentatus)、Ollulanus属、夏伯特线虫属(Chabertia)、猪肾虫、气管比翼线虫(Syngamustrachea)、Ancylostoma属、钩虫属(Uncinaria)、球首线虫属(Globocephalus)、Necator属、后圆线虫属(Metastrongylus)、毛样缪勒线虫(Muellerius capillaris)、Protostrongylus 属、管圆线虫属(Angiostrongylus)、Parelaphostrongylus属、Aleurostrongylus abstrusus和肾膨结线虫(Dioctophyma renal);
肠线虫(蛔目(Ascaridida)),例如似蚓蛔线虫(Ascaris lumbricoides)、猪蛔虫(Ascaris suum)、鸡蛔虫(Ascaridia galli)、马副蛔虫(Parascarisequorum)、蛲虫(Enterobius vermicularis)(蛲虫)、犬弓首蛔虫(Toxocaracanis)、犬蛔虫(Toxascaris leonine)、Skrjabinema属和马尖尾线虫(Oxyurisequi);
Camallanida,例如Dracunculus medinensis(麦地那龙线虫);
旋尾目(Spirurida),例如Thelazia属、丝虫属(Wuchereria)、Brugia属、Onchocerca属、Dirofilari属、Dipetalonema属、Setaria属、Elaeophora属、狼尾旋线虫(Spirocerca lupi)和丽线虫属(Habronema);
棘头虫(棘头动物门(Acanthocephala)),例如Acanthocephalus属、猪巨吻棘头虫(Macracanthorhynchus hirudinaceus)和棘头虫属(Oncicola);
扁虫类(Planarians)(扁形动物门(Plathelminthes)):
肝吸虫(Flukes)(吸虫纲(Trematoda)),例如肝片形吸虫属(Faciola)、Fascioloides magna、并殖吸虫属(Paragonimus)、双腔吸虫属(Dicrocoelium)、布氏姜片吸虫(Fasciolopsis buski)、华枝睾吸虫(Clonorchissinensis)、血吸虫属(Schistosoma)、毛毕吸虫属(Trichobilharzia)、有翼翼形吸虫(Alaria alata)、并殖吸虫属和Nanocyetes属;
Cercomeromorpha,尤其是Cestoda(绦虫),例如裂头绦虫属(Diphyllobothrium)、Tenia属、棘球绦虫属(Echinococcus)、犬复孔绦虫(Dipylidium caninum)、Multiceps属、膜壳绦虫属(Hymenolepis)、中殖孔绦虫属(Mesocestoides)、Vampirolepis属、Moniezia属、Anoplocephala属、Sirometra属、Anoplocephala属和Hymenolepis属。
式(I)化合物和包含它们的组合物尤其可用于防治双翅目、蚤目和蜱亚目的害虫。
此外,尤其优选式(I)化合物、其N-氧化物或盐以及包含它们的组合物在在防治蚊子中的用途。
式(I)化合物、其N-氧化物或盐以及包含它们的组合物在防治苍蝇中的用途是本发明的另一优选实施方案。
此外,尤其优选式(I)化合物、N-氧化物或盐以及包含它们的组合物在防治蚤中的用途。
式(I)化合物、其N-氧化物或盐以及包含它们的组合物在防治壁虱中的用途是本发明的另一优选实施方案。
式(I)化合物、其N-氧化物或盐还尤其可以用于防治体内寄生虫(蛔虫、棘头虫和扁虫类)。
给药可以预防和治疗方式进行。
活性化合物的给药直接或以合适的制剂形式口服、局部/经皮或肠胃外进行。
为了对温血动物口服给药,可以将式(I)化合物、其N-氧化物或可兽用盐可以配制成动物饲料、动物饲料预混物、动物饲料浓缩物、丸剂、溶液、糊、悬浮液、浸液、凝胶、片剂、大丸剂和胶囊。此外,式(I)化合物、其N-氧化物或可兽用盐可以在其饮用水中给药于动物。对于口服给药,所选择的剂型应为动物提供0.01-100mg/kg动物体重/天,优选0.5-00mg/kg动物体重/天的式(I)化合物。
或者,式(I)化合物可以肠胃外给药于动物,例如通过腔内、肌内、静脉内或皮下注射。式(I)化合物可以分散或溶于对于皮下注射而言生理上可接受的载体中。或者,式(I)化合物配制成皮下给药用植入物。此外,式(I)化合物可以透皮给药于动物。对于肠胃外给药,所选剂型应为动物提供0.01-100mg/kg动物体重/天的式(I)化合物。
式(I)化合物还可以浸液、粉剂、粉末、套环、挂牌(medallions)、喷雾剂、香波、滴施(spot-on)和喷淋(pour-on)配制剂形式以及以软膏或水包油或油包水乳液局部给药于动物。对于局部施用,浸液和喷雾剂通常含有0.5-5000ppm,优选1-3000ppm式(I)化合物。此外,式(I)化合物可以配制成动物,特别是四足动物如牛和绵羊用耳贴。
合适的制剂是:
-溶液,如口服溶液、稀释后口服给药用浓缩物、用于皮肤上或用于体腔内的溶液、喷淋配制剂、凝胶;
-口服或皮肤给药乳液和悬浮液;半固体制剂;
-其中将活性化合物在软膏基质中或在水包油或油包水乳液基质中加工的配制剂;
-固体制剂如粉末、预混物或浓缩物、颗粒、丸剂、片剂、大丸剂、胶囊;气雾剂和吸入剂,以及含有活性化合物的成型制品。
适合注射的组合物通过将活性成分溶于合适的溶剂中并任选加入其他成分如酸、碱、缓冲盐、防腐剂和加溶剂而制备。过滤这些溶液并无菌填充。
合适的溶剂是生理上耐受的溶剂如水,链烷醇如乙醇、丁醇、苄醇、甘油、丙二醇、聚乙二醇,N-甲基-吡咯烷酮、2-吡咯烷酮及其混合物。
活性化合物可以任选溶于生理上耐受的且适合注射的植物或合成油中。
合适的加溶剂是促进活性化合物在主溶剂中溶解或防止其沉淀的溶剂。实例是聚乙烯基吡咯烷酮、聚乙烯醇、聚氧乙基化蓖麻油和聚氧乙基化脱水山梨糖醇。
合适的防腐剂是苄醇、三氯丁醇、对羟基苯甲酸酯和正丁醇。
口服溶液直接给药。浓缩物在预先稀释至使用浓度之后口服给药。口服溶液和浓缩物根据上面对注射液所述的现有技术制备,并不必需无菌程序。
用于皮肤上的溶液滴施、涂施、擦施、洒施或喷施。
用于皮肤上的溶液根据现有技术以及上面对注射液所述制备,并不必需无菌程序。
其他合适的溶剂是聚丙二醇,苯基乙醇,苯氧基乙醇,酯类如乙酸乙酯或乙酸丁酯、苯甲酸苄基酯,醚类如亚烷基二醇烷基醚,例如二丙二醇单甲醚,酮类如丙酮、甲基乙基酮,芳族烃类,植物和合成油,二甲基甲酰胺(DMF),二甲基乙酰胺,乙二醇单乙基醚(transcutol),丙酮缩甘油(solketal),碳酸亚丙基酯,以及它们的混合物。
可能有利的是在制备过程中加入增稠剂。合适的增稠剂是无机增稠剂如膨润土、胶态硅酸、单硬脂酸铝,有机增稠剂如纤维素衍生物、聚乙烯醇及其共聚物、丙烯酸酯和甲基丙烯酸酯。
将凝胶施加或涂敷在皮肤上或引入体腔中。凝胶通过用足以得到具有软膏状稠度的透明材料的增稠剂处理如在注射液情况下所述制备的溶液而制备。所用增稠剂是上面所给增稠剂。
将喷淋配制剂倒在或喷雾在限定的皮肤区域,活性化合物渗透进皮肤并内吸起作用。
喷淋配制剂通过将活性化合物在合适的皮肤相容性溶剂或溶剂混合物中溶解、悬浮或乳化而制备。合适的话加入其他助剂如着色剂、生物吸收促进物质、抗氧化剂、光稳定剂、粘合剂。
合适的溶剂是水,链烷醇,二醇,聚乙二醇,聚丙二醇,甘油,芳族醇如苄醇,苯基乙醇,苯氧基乙醇,酯如乙酸乙酯,乙酸丁酯,苯甲酸苄基酯,醚如亚烷基二醇烷基醚如二丙二醇单甲基醚、二甘醇单丁基醚,酮如丙酮、甲基乙基酮,环状碳酸酯如碳酸亚丙基酯、碳酸亚乙基酯,芳族和/或脂族烃类,植物或合成油,DMF,二甲基乙酰胺,正烷基吡咯烷酮如甲基吡咯烷酮、正丁基吡咯烷酮或正辛基吡咯烷酮、N-甲基吡咯烷酮、2-吡咯烷酮、2,2-二甲基-4-氧基亚甲基-1,3-二氧戊环和甘油缩甲醛。
合适的着色剂是所有允许用在动物上且可以溶解或悬浮的着色剂。
合适的吸收促进物质例如为DMSO,涂施油如肉豆蔻酸异丙基酯、二丙二醇壬酸酯、硅油及其与聚醚的共聚物,脂肪酸酯,甘油三酯,脂肪醇。
合适的抗氧化剂是亚硫酸盐或偏亚硫酸氢盐如偏亚硫酸氢钾、抗坏血酸、丁基羟基甲苯、丁基羟基茴香醚、生育酚。
合适的光稳定剂例如为2-苯基苯并咪唑-5-磺酸(novantisolic acid)。
合适的粘合剂例如为纤维素衍生物、淀粉衍生物、聚丙烯酸酯、天然聚合物如藻酸盐、明胶。
乳液可以口服、经皮给药或作为注射液给药。
乳液呈油包水型或水包油型。
它们通过将活性化合物溶于疏水性或亲水性相中并借助合适的乳化剂以及合适的话其他助剂如着色剂、吸收促进物质、防腐剂、抗氧化剂、光稳定剂、粘度提高物质用另一相的溶剂均化而制备。
合适的疏水相(油)是:
-液体石蜡,硅油,天然植物油如芝麻油、杏仁油、蓖麻油,合成甘油三酯如甘油二辛酸/癸酸酯,含链长为C8-C12的植物脂肪酸或其他具体选定的天然脂肪酸的甘油三酯混合物或,可能的话还含有羟基的饱和或不饱和脂肪酸的部分甘油酯混合物,C8-C10脂肪酸的甘油单酯和甘油二酯,-脂肪酸酯如硬脂酸乙基酯、己二酸二正丁基酯、月桂酸己基酯、二丙二醇壬酸酯、中等链长的脂肪酸与链长为C16-C18的饱和脂肪醇的酯、肉豆蔻酸异丙基酯、棕榈酸异丙基酯、链长为C12-C18的饱和脂肪醇的辛酸/癸酸酯、硬脂酸异丙基酯、油酸油基酯、油酸癸基酯、油酸乙基酯、乳酸乙基酯、蜡状脂肪酸如合成鸭尾脂腺脂肪、邻苯二甲酸二丁酯、己酸二异丙基酯以及与后者相关的酯混合物,
-脂肪醇如异十三烷醇、2-辛基十二烷醇、十六烷基十八烷基醇、油醇,以及
-脂肪酸如油酸,和
-它们的混合物。
合适的亲水相是水,醇如丙二醇、甘油、山梨醇及其混合物。
合适的乳化剂是:
-非离子表面活性剂,例如聚乙氧基化蓖麻油、聚乙氧基化脱水山梨糖醇单油酸酯、脱水山梨糖醇单硬脂酸酯、甘油单硬脂酸酯、聚氧乙基硬脂酸酯、烷基酚聚乙二醇醚;
-两性表面活性剂,例如N-月桂基对亚氨基二丙酸二钠或卵磷脂;
-阴离子表面活性剂,例如月桂基硫酸钠、脂肪醇醚硫酸盐、聚乙二醇单/二烷基醚正磷酸酯单乙醇胺盐;
-阳离子表面活性剂,如十六烷基三甲基氯化铵。
合适的其他助剂是提高粘度并稳定乳液的物质,如羧甲基纤维素、甲基纤维素和其他纤维素以及淀粉衍生物,聚丙烯酸酯,藻酸盐,明胶,阿拉伯树胶,聚乙烯基吡咯烷酮,聚乙烯醇,甲基乙烯基醚和马来酸酐的共聚物,聚乙二醇,蜡,胶态硅酸或所述物质的混合物。
悬浮液可以口服或局部/经皮给药。它们通过将活性化合物悬浮于悬浮剂中而制备,合适的话加入其他助剂如润湿剂、着色剂、生物吸收促进物质、防腐剂、抗氧化剂、光稳定剂。
液态悬浮剂是所有均相溶剂和溶剂混合物。
合适的润湿剂(分散剂)是上面所给的乳化剂。
可以提到的其他助剂是上述那些。
半固体制剂可以口服或局部/经皮给药。它们与上述悬浮液和乳液的不同仅在于它们具有更高粘度。
为了生产固体制剂,将活性化合物与合适的赋形剂混合,合适的话加入助剂,并且制成所需剂型。
合适的赋形剂是所有生理上耐受的固体惰性物质。所用那些是无机和有机物质。无机物质例如为氯化钠,碳酸盐如碳酸钙,碳酸氢盐,铝氧化物,二氧化钛,硅酸,泥质土,沉淀或胶态二氧化硅或磷酸盐。有机物质例如为糖类、纤维素、食品和饲料如奶粉、动物粉、谷粉和屑、淀粉。
合适的助剂是上面所述的防腐剂、抗氧化剂和/或着色剂。
其他合适的助剂是润滑剂和助滑剂如硬脂酸镁、硬脂酸、滑石、膨润土、崩解促进物质如淀粉或交链的聚乙烯基吡咯烷酮、粘合剂如淀粉、明胶或线性聚乙烯基吡咯烷酮以及干粘合剂如微晶纤维素。
通常而言,“杀寄生虫有效量”是指指对生长获得可观察到的效果所需的活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀寄生虫有效量可以变化。组合物的杀寄生虫有效量也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
可以用于本发明中的组合物可以包含约0.001-95%式(I)化合物或其N-氧化物或盐。
通常而言,有利的是以0.5-100mg/kg/天,优选1-50mg/kg/天的总量施用式(I)化合物。
即用制剂以10ppm-80重量%,优选0.1-65重量%,更优选1-50重量%,最优选5-40重量%的浓度含有对寄生虫,优选体外寄生虫起作用的化合物。
在使用前稀释的制剂以0.5-90重量%,优选1-50重量%的浓度含有对体外寄生虫起作用的化合物。
此外,制剂以10ppm-2重量%,优选0.05-0.9重量%,非常特别优选0.005-0.25重量%的浓度包含对抗体内寄生虫的式(I)化合物。
在本发明的优选实施方案中,经皮/局部施用包含式(I)化合物的组合物。
在另一优选实施方案中,局部施用以含有化合物的成型制品如套环、挂牌、耳贴、在身体部分上固定用的绑带以及粘合条和箔的形式进行。
通常有利的是施用在三周内以10-300mg/kg,优选20-200mg/kg,最优选25-160mg/kg被处理动物体重的总量释放式(I)化合物的固体配制剂。
为了制备成型制品,使用热塑性和柔性塑料以及弹性体和热塑性弹性体。合适的塑料和弹性体是与式(I)化合物充分相容的聚乙烯基树脂、聚氨酯、聚丙烯酸酯、环氧树脂、纤维素、纤维素衍生物、聚酰胺和聚酯。塑料和弹性体的详细列表以及成型制品的制备程序例如在WO 03/086075中给出。
根据本发明使用的组合物还可以含有其他活性成分,例如其他农药、杀虫剂、除草剂、杀真菌剂、其他杀虫剂和杀菌剂,肥料如硝酸铵、尿素、钾碱和过磷酸钙,植物毒素和植物生长调节剂、安全剂和杀线虫剂。这些额外成分可以与上述组合物依次或结合使用,合适的话还在紧临使用前加入(桶混物)。例如可以在用其他活性成分处理之前或之后用本发明组合物喷雾植物。
这些试剂可以1∶10-10∶1的重量比与本发明所用试剂混合。将作为杀虫剂使用的化合物(I)或包含它们的组合物与其他农药混合通常导致更宽的杀虫作用谱。
式(I)化合物可以与其一起使用的下列农药用来说明可能的组合,但不施加任何限制:
有机(硫代)磷酸酯类:高灭磷(acephate)、唑啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、谷硫磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(chlorfenvinphos)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、丙线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、噻唑硫磷(fosthiazate)、庚烯磷(heptenophos)、异噁唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(meearbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、甲基一六零五(methyl-parathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、砜吸磷(oxydemeton-methyl)、对氧磷(paraoxon)、一六零五(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、甲拌磷(phorate)、辛硫磷(phoxim)、嘧啶磷(pirimiphos)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、巴胺磷(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、乙丙硫磷(sulprophos)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁磷(terbufos)、杀虫威(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭磷(vamidothion);
氨基甲酸酯类:棉铃威(alanycarb)、涕灭威(aldicarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮氧威(butoxycarboxim)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、ethiofoncarb、仲丁威(fenobucarb)、双氧威(fenoxycarb)、抗螨脒(formethanat)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、XMC、灭杀威(xylylcarb);
合成除虫菊酯类:氟丙菊酯(acrinathrin)、丙烯除虫菊(allethrin)、右旋丙烯菊酯(d-cis-trans allethrin)、右旋反式丙烯菊酯(d-trans allethrin)、氟氯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、2-环戊烯基生物烯丙菊酯(bioallethrin S-cyclopentenyl)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、高效氟氯氰菊酯(beta-cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、氯氟氰菊酯(lambda-cyhalothrin)、精高效氯氟氰菊酯(gamma-cyhalothrin)、苯醚氰菊酯(cyphenothrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、高效反式氯氰菊酯(theta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(empenthrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(tau-fluvalinate)、溴氟醚菊酯(halfenprox)、咪炔菊酯(imiprothrin)、氯菊酯(permethrin)、苯醚菊酯(phenothrin)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、除虫菊酯I(pyrethrin I)和除虫菊酯II、灭虫菊(resmethrin)、RU 15525、灭虫硅醚(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin)、ZXI8901;
生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类;双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟虫酰脲(noviflumuron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(buprofezin)、噁茂醚(diofenolan)、噻螨酮(hexythiazox)、特苯噁唑(etoxazole)、四螨嗪(clofentazine);b)蜕皮激素拮抗剂:可芬洛(chlormafenozide)、特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、艾扎丁(azadirachtin);c)保幼激素类似物:蚊蝇醚(pyriproxyfen)、蒙512(hydroprene)、烯虫炔酯(kinoprene)、蒙五一五(methoprene)、双氧威(fenoxycarb);d)类脂生物合成抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat);
烟酸受体激动剂/拮抗剂化合物:吡虫清(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、硝胺烯啶(nitenpyram)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、烟碱(nicotine)、杀虫磺(bensultap)、杀螟丹(cartap hydrochloride)、杀虫环(thiocyclam)、杀虫双(thiosultap-sodium);
式(Г1)的噻唑化合物:
GABA拮抗剂化合物:乙酰虫腈(acetoprole)、氯丹(chlordane)、硫丹(endosulfan)、乙虫腈(ethiprole)、林丹(gamma-HCH(lindane))\锐劲特(fipronil)、氟吡唑虫(vaniliprole)、pyrafluprole、pyriprole、式Г2的苯基吡唑化合物:
大环内酯杀虫剂:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、米尔螨素(milbemectin)、lepimectin、艾克敌105(spinosad);
METI I化合物:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、flufenerim、哒螨酮(pyridaben)、嘧螨醚(pyrimidifen)、鱼藤酮(rotenone)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad);
METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
解偶联剂化合物:氟唑虫清(chlorfenapyr)、二硝酚(DNOC);
氧化磷酸化抑制剂化合物:三唑锡(azocyclotin)、三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite)、三氯杀螨砜(tetradifon);
蜕皮干扰剂化合物:cryomazine;
混合功能氧化酶抑制剂化合物:增效醚(piperonyl butoxide);
钠通道阻断剂化合物:噁二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
无机化合物:磷化铝、硼砂、冰晶石、氰化物、磺酰氟、膦;
昆虫中肠膜的微生物干扰剂:苏云金芽孢杆菌以色列亚种(bacillusthuringiensis subsp.Israelensis)、球形芽孢杆菌(bacillus sphaericus)、苏云金芽胞杆菌鲇泽亚种(bacillus thuringiensis subsp.Aizawai)、bacillusthuringiensis subsp.Kurstaki、苏云金芽胞杆菌拟步行甲亚种菌株(bacillusthuringiensis subsp.Tenebrionis);
其他各种:双甲脒(amitraz)、benclothiaz、苯螨特(benzoximat)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、杀螟丹(cartap)、喹菌酮(chinomethionat)、氯化苦(chloropicrin)、氟啶虫酰胺(flonicamid)、溴甲烷(methyl bromide)、啶虫丙醚(pyridalyl)、据嗪酮(pymetrozine)、ryn axypursulfur、酒石酸氧锑钾(tartar emetic)、硫环杀(thiocyclam)、tribufosflubendiamide、cyenopyrafen、吡氟硫磷(flupyrazofos)、丁氟螨酯(cyflumetofen)、amidoflumet、NNI-0101、N-R’-2,2-二halo-1-R”环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟对甲苯基)腙或N-R’-2,2-二(R”’)丙酰胺-2-(2,6-二氯-α,α,α-三氟对甲苯基)腙,其中R’为甲基或乙基,halo为氯或溴,R”为氢或甲基且R”’为甲基或乙基,式Г3的邻氨基苯甲酰胺化合物:
其中A1为CH3、Cl、Br、I,X为C-H、C-Cl、C-F或N,Y’为F、Cl或Br,Y”为F、Cl、CF3,B1为氢、Cl、Br、I、CN,B2为Cl、Br、CF3、OCH2CF3、OCF2H且RB为氢、CH3或CH(CH3)2,以及如JP 2002284608、WO 02/89579、WO 02/90320、WO 02/90321、WO 04/06677、WO 04/20399或JP 200499597中所述的丙二腈化合物。
本发明的式(I)化合物还可以与氟代喹唑啉酮化合物如下列化合物组合:
1-乙酰基-3-[(吡啶-3-基甲基)氨基]-6-(1,2,2,2-四氟-1-三氟甲基乙基)-3,4-二氢-1H-喹唑啉-2-酮。
本发明的式(I)化合物还可以嘧啶基炔基醚化合物Г4或噻二唑基炔基醚化合物Г5组合:
其中R为甲基或乙基且Het*为3,3-二甲基吡咯烷-1-基、3-甲基哌啶-1-基、3,5-二甲基哌啶-1-基、4-甲基哌啶-1-基、六氢氮杂-1-基、2,6-二甲基六氢氮-1-基或2,6-二甲基吗啉-4-基。这些化合物例如描述于JP 2006131529中。
上述混合组分有市售且尤其可以在The Pesticide Manual,第13版,British Crop Protection Council(2003)中找到。
式Г2的硫羰胺及其制备已经描述于WO 98/28279中。
Lepimection由Agro Proj ect,PJB Publications Ltd,2004年11月已知。Benclothiaz及其制备已经描述于EP-A1454621中。杀扑磷和对氧磷及其制备已经描述于Farm Chemicals Handbook,第88卷,MeisterPublishing Company,2001中。乙酰虫腈及其制备已经描述于WO 98/28277中。氰氟虫胺及其制备已经描述于EP-A1462456中。吡氟硫磷已经描述于Pesticide Science 54,1988,第237-243页和US 4822779中。Pyrafluprole及其制备已经描述于JP 2002193709和WO 01/00614中。Pyriprole及其制备已经描述于WO 98/45274和US 6335357中。Amidoflumet及其制备已经描述于US 6221890和JP 21010907中。Flufenerim及其制备已经描述于WO 03/007717和WO 03/007718中。丁氟螨酯及其制备已经描述于WO04/080180中。
式Г3的邻氨基苯甲酰胺化合物其制备已经描述于WO 01/70671;WO02/48137;WO 03/24222,WO 03/15518,WO 04/67528;WO 04/33468和WO 05/118552中。
杀真菌混合组分是选自如下的那些:
-酰基丙氨酸类,例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl);
-胺衍生物,例如4-十二烷基-2,6-二甲基吗啉(aldimorph)、多果定(dodine)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、双胍盐(guazatine)、双胍辛醋酸盐(iminoctadine)、螺噁茂胺(spiroxamine)、克啉菌(tridemorph);
-苯胺基嘧啶类,例如二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)或环丙嘧啶(cyprodinil);
-抗菌素,例如放线菌酮(cycloheximid)、灰黄霉素(griseofulvin)、春雷素(kasugamycin)、多马霉素(natamycin)、多氧霉素(polyoxin)和链霉素(streptomycin);
-唑类,例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazol)、环唑醇(cyproconazole)、噁醚唑(difenoconazole)、烯唑醇(diniconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙氯灵(prochloraz)、丙硫菌唑(prothioconazole)、戊唑醇(tebuconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizol)、戊叉唑菌(triticonazole)、粉唑醇(flutriafol);
-二羧酰亚胺类,例如异丙定(iprodion)、甲菌利(myclozolin)、杀菌利(procymidon)、烯菌酮(vinclozolin);
-二硫代氨基甲酸盐类,例如福美铁(ferbam)、代森钠(nabam)、代森锰(maneb)、代森锰锌(mancozeb)、威百亩(metam)、代森联(metiram)、甲基代森锌(propineb)、福代锌(polycarbamate)、福美双(thiram)、福美锌(ziram)、代森锌(zineb);
-杂环化合物,例如敌菌灵(anilazine)、苯菌灵(benomyl)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、氰霜唑(cyazofamid)、棉隆(dazomet)、二噻农(dithianon)、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、异嘧菌醇(fenarimol)、麦穗宁(fuberidazole)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、稻瘟灵(isoprothiolane)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、啶斑肟(pyrifenox)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、硅噻菌胺(silthiofam)、涕必灵(thiabendazole)、溴氟唑菌(thifluzamid)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)、嗪氨灵(triforine);
-铜杀真菌剂,例如波尔多液(Bordeaux混合物)、乙酸铜、王铜、碱式硫酸铜;
-硝基苯基衍生物,例如如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)、异丙消(nitrophthal-isopropyl);
-苯基吡咯类,例如拌种咯(fenpiclonil)或氟噁菌(fludioxonil);
-硫;
-其它杀真菌剂,例如噻二唑素(acibenzolar-S-methyl)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、哒菌清(diclomezine)、双氯氰菌胺(diclocymet)、乙霉威(diethofencarb)、克瘟散(edifenphos)、噻唑菌胺(eth aboxam)、环酰菌胺(fenhexamide)、薯瘟锡(fentin-acetate)、氰菌胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、苯菌酮(metrafenone)、戊菌隆(pencycuron)、百维灵(propamocarb)、四氯苯酞(phthalide)、甲基立枯磷(tolclofos-methyl)、五氯硝基苯(quintozene)、苯酰菌胺(zoxamide);
-嗜球果伞素类(strobilurins),如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)或肟菌酯(trifloxystrobin);
-次磺酸衍生物,如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)、对甲抑菌灵(tolylfluanid);
-肉桂酰胺及类似化合物,如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)、氟吗啉(flumorp)。
动物害虫,即节肢动物和线虫,植物、其中植物生长的土壤或水体可以通过本领域已知的任何施用方法与本发明化合物(I)、其N-氧化物或盐或包含它们的组合物接触。这里的“接触”包括直接接触(将化合物/组合物直接施用于动物害虫或植物上,通常施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于动物害虫或植物的场所)。
此外,动物害虫可以通过使目标害虫,其食物供应源、栖息地、繁殖地或其场所与杀寄生虫有效量的式(I)化合物、其N-氧化物或盐接触而防治。这里的施用可以在场所、生长中的作物或收获的作物被害虫侵染之前或之后进行。
“场所”是指害虫或寄生虫生长或可能生长的栖息地、繁殖地、植物、种子、土壤、区域、材料或环境。
通常而言,“杀虫有效量”是指对生长获得可观察到的效果所需的活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀虫有效量可以变化。组合物的杀虫有效量也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
式(I)化合物、其N-氧化物或盐以及包含它们的组合物可以用于保护木质材料如树木、护栏、枕木等,以及建筑物如房子、附属建筑、工厂,还有建筑材料、家具、皮革、纤维、乙烯基制品、电线和电缆等以防蚂蚁和/或白蚁,并防止蚂蚁和白蚁损害作物或人类(例如当害虫侵入房子和公共设施时)。式(I)化合物不仅施用于周围的土壤表面或地板下的土壤中以保护木质材料,而且还可以施用于堆积制品如地板下混凝土、亭柱、梁、胶合板、家具等的表面,木质制品如碎料板、半包板(halfboard)等以及乙烯基制品如包覆的电线、乙烯基片材,绝热材料如苯乙烯泡沫等。在防止蚂蚁损害作物或人类的施用中,将本发明的蚂蚁防治剂施用于作物或周围土壤,或直接施用于蚂蚁的巢穴等。
本发明化合物还可以预防性地施用于预期出现害虫的地方。
式(I)化合物、其N-氧化物或盐还可以通过使生长的植物与杀虫有效量的式(I)化合物接触而用于保护生长中的植物免受害虫侵袭或侵染。这里的“接触”包括直接接触(将化合物/组合物直接施用于害虫和/或植物上,通常施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于害虫和/或植物的场所)。
在土壤处理或施用于害虫居住地或巢穴的情况下,活性成分量为0.0001-500g/100m2,优选0.001-20g/100m2。
在材料保护中的常规施用率例如为0.01-1000g活性化合物/m2被处理材料,理想的是0.1-50g/m2。
用于材料浸渍中的杀虫组合物通常含有0.001-95重量%,优选0.1-45重量%,更优选1-25重量%至少一种驱避剂和/或杀虫剂。
为了用于诱饵组合物中,活性成分的典型含量为0.001-15重量%,理想的是0.001-5重量%活性化合物。
为了用于喷雾组合物中,活性成分的含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
为了用于处理作物植株,本发明活性成分的施用率可以为0.1-4000g/ha,理想的是25-600g/ha,更理想的是50-500g/ha。
在种子处理中,该混合物的施用率通常为0.1g-10kg/100kg种子,优选1g-5kg/100kg种子,尤其是1-200g/100kg种子。
现在通过下列实施例更详细说明本发明。
I.试验程序
通过适当改变起始化合物,使用下列实施例所示程序得到其他化合物(I)。所得化合物与物理数据一起列于下表C中。
产物通过联用高效液相色谱/质谱(HPLC/MS)、在CDCl3或d6-DMSO中的1H-NMR(400MHz)或其熔点表征。HPLC柱:RP-18柱(德国MerckKgaA的Chromolith Speed ROD)。洗脱:比例为5∶95-95∶5的乙腈+0.1%三氟乙酸(TFA)/水,5分钟,40℃。MS:Quadrupol电喷射离子化,80V(正模式)。
I.1.1制备溴代磺酰胺(II.B)
I.1.1.a)制备4-溴-3-氟-N-[(喹啉-4-基)甲基]苯磺酰胺(R1=F)
将喹啉甲基胺(61g,0.023mol)在三乙胺(3.81ml,0.027mol)中的溶液加入3-氟-4-溴-磺酰氯(6.24g,0.023mol)的溶液中。将该混合物在环境温度下搅拌16小时。加入水(20ml);滤出沉淀,然后用水和甲基叔丁基醚漂洗并干燥,得到无色固体状标题化合物(4.92g)。1H-NMR(400MHz,d6-DMSO):δ=8.8(m,1h),8.6(m,1h),8.1-7.8(m,3H),7.8-7.4(m,5h),4.6ppm(s,2H)。
I.1.1.b)制备4-溴-3-三氟甲基-N-[(喹啉-4-基)甲基]苯磺酰胺(R1=CF3)
使用类似于在1.1.1.a)下所述的方法制备该化合物。1H-NMR(400MHz,d6-DMSO):δ=8.8(m,2H),8.1(m,8H),4.6ppm(s,2H)。
I.1.1.c)制备4-溴-3-甲基-N-[(喹啉-4-基)甲基]苯磺酰胺(R1=CH3)
使用类似于在1.1.1.a)下所述的方法制备该化合物。1H-NMR(400MHz,d6-DMSO):δ=8.8(m,1H),8.5(t,1H),8.2-8.0(m,2H),7.8-7.5(m,6H),4.6(d,2H),2.4ppm(s,3H)。
I.1.1.d)制备4-溴-3-氯-N-[(喹啉-4-基)甲基]苯磺酰胺(R1=Cl)
使用类似于在1.1.1.a)下所述的方法制备该化合物。1H-NMR(400MHz,d6-DMSO):δ=8.8(m,1H),8.6(t,1H),8.1-7.6(m,8H),4.6ppm(d,2H)。
I.1.2制备溴代磺酰胺(II.B*)
I.1.2.a)制备4-溴-2-氟-N[(喹啉-4-基)甲基]苯磺酰胺(R1=F)
使用类似于在1.1.1.a)下所述的方法制备该化合物。1H-NMR(400MHz,d8-THF):δ=8.6(m,1H),8.1(m,1H),8.0(m,1H),7.6-7.4(m,5H),7.2(m,2H),4.5(d,2H)。
I.1.2.b)制备4-溴-2-甲基-N[(喹啉-4-基)甲基]苯磺酰胺(R1=CH3)
使用类似于在1.1.1.a)下所述的方法制备该化合物。1H-NMR(400MHz,d6-DMSO):δ=8.8(m,1H),8.6(m,1H),8.1-8.0(m,2H),7.8-7.4(m,6H),7.2(m,2H),4.5(d,2H),2.5(s,3H)。
I.1.2.c)制备4-溴-2-三氟甲氧基-N[(喹啉-4-基)甲基]苯磺酰胺(R1=OCF3)
使用类似于在1.1.1.a)下所述的方法制备该化合物。1H-NMR(400MHz,d6-DMSO):δ=8.8(m,1H),8.1-8.0(m,2H),7.8-7.4(m,7H),7.2(m,2H),4.5(d,2H)。
I.1.2.d)制备4-溴-2-氯-N[(喹啉-4-基)甲基]苯磺酰胺(R1=Cl)
使用类似于在1.1.1.a)下所述的方法制备该化合物。1H-NMR(400Mhz,d6-DMSO):δ=8.8(br,2H),8.1-7.9(m,2H),7.8-7.4(m,6H),7.2(m,2H),4.6(d,2H)。
I.1.2.e)制备4-溴-2-三氟甲基-N[(喹啉-4-基)甲基]苯磺酰胺(R1=CF3)
使用类似于在1.1.1.a)下所述的方法制备该化合物。1H-NMR(400Mhz,d6-DMSO):δ=8.8(m,2H),8.2-7.6(m,5H),7.7(m,1H),7.6(m,1H),7.4(m,1H),4.5(d,2H)。
I.2制备化合物(I)的通用程序
使合适的上述通式(II)的磺酰胺(0.48mmol)、Cs2CO3(200mg)、聚苯乙烯-三苯基膦-Pd(400mg,Argonaut)和硼酸(0.6mmol)在四氢呋喃(3ml)和水(0.5ml)中的混合物在75℃下反应。20小时后将该混合物冷却至环境温度并用聚苯乙烯-二乙醇胺(100mg,Novabiochem)处理6小时。将固定化反应物滤出并用四氢呋喃(10ml)漂洗。收集滤液并真空除去挥发物。对残余物进行柱层析(SiO2,环己烷/乙酸乙酯)。
代表性化合物的分析数据给于表C和表D中。
根据上述程序制备表C中所列式(I.B)化合物。
表C
化合物 | R1 | R2a | R2b | R2c | MS(m/e[M+]) | HPLCa)或1H-NMRb) |
B1 | CH3 | Cl | H | Cl | 456.9 | 3.20 |
B2 | CH3 | H | CH3 | H | 402.5 | 2.91 |
B3 | CH3 | H | H | CF3 | 457.4 | 3.13 |
B4 | CH3 | H | F | H | 406.5 | 2.77 |
B5 | CH3 | Cl | H | H | 422.9 | 2.86 |
B6 | CH3 | F | H | H | 406.5 | 2.68 |
B7 | CH3 | H | H | OCF3 | 473.4 | 3.21 |
B8 | Cl | H | F | H | 426.9 | 2.81 |
B9 | F | Cl | H | Cl | 461.3 | 3.08 |
B10 | F | H | CH3 | H | 406.5 | 2.88 |
B11 | F | H | H | CF3 | 460.4 | 3.07 |
B12 | F | H | F | H | 410.4 | 2.76 |
B13 | F | F | H | H | 410.4 | 2.70 |
B14 | F | H | H | OCF3 | 476.4 | 3.15 |
B15 | CF3 | H | CH3 | H | 456.5 | 3.06 |
B16 | CF3 | H | H | CF3 | 510.5 | 3.23 |
B17 | CF3 | H | F | H | 460.5 | 2.96 |
B18 | CF3 | H | H | OCF3 | 526.5 | 3.32 |
B19 | CF3 | H | H | CN | 467.5 | 2.76 |
B20 | CF3 | H | H | O-CF=CF2 | 538.5 | 3.36 |
B21 | Cl | CF3 | H | CF3 | n.d.c) | 8.8m,8.2m,8.1m,8.0m,7.9m,7.8-7.7m,7.6m,7.4m,7.2m,4.8d |
B22 | Cl | Cl | H | Cl | n.d.c) | 8.8m,8.1m,8.1m,7.9m,7.8m,7.6m,7.5m,7.4m,7.2m,7.1m,5.2t,4.8d |
B23 | Cl | Cl | H | CF3 | n.d.c) | 8.8m,8.1m,8.1m,7.9m,7.8m,7.6m,7.5m,7.4m,7.2m,7.1m,5.2t,4.8d |
B24 | Cl | H | H | CF3 | n.d.c) | 8.8m,8.2m,8.0m,7.8-7.6m,75m,7.4m, |
化合物 | R1 | R2a | R2b | R2c | MS(m/e[M+]) | HPLCa)或1H-NMRb) |
7.3m,7.2m,5.2t,4.8d | ||||||
B25 | Cl | H | H | OCH3 | n.d.c) | 8.8m,8.2m,7.9m,7.9-7.6m,7.3m,7.1m,7.0m,5.2t,4.8d |
B26 | Cl | F | H | H | n.d.c) | 8.8m,8.2m,7.9m,7.7m,7.6m,7.5-7.1m,5.2t,4.8d |
B27 | Cl | CH3 | H | OCH3 | n.d.c) | 8.8m,8.2m,8.0m,7.7m,7.6m,7.3m,7.2m,7.0m,6.8m,5.2t,4.8d |
B28 | CH3 | H | Cl | H | 422.9 | 2.94 |
B29 | CH3 | F | H | Br | 485.4 | 3.04 |
B30 | CH3 | H | H | CN | 414.0 | 2.6 |
B31 | CH3 | F | H | Cl | 440.9 | 2.97 |
B32 | CH3 | Cl | H | CF3 | 490.9 | 3.19 |
B33 | CH3 | H | CF3 | Cl | 490.9 | 3.23 |
B34 | CH3 | F | H | OCH3 | 436.5 | 2.34 |
B35 | Cl | H | Cl | H | 443.4 | 3.00 |
B36 | Cl | H | H | CN | 433.9 | 2.63 |
B37 | Cl | F | H | Cl | 461.3 | 3.03 |
B38 | Cl | H | CF3 | Cl | 511.3 | 3.31 |
B39 | Cl | F | H | OCH3 | 456.9 | 2.52 |
B40 | F | H | Cl | H | 426.9 | 2.94 |
B41 | F | H | H | CN | 417.5 | 2.55 |
B42 | F | F | H | Cl | 444.9 | 2.97 |
B43 | F | Cl | H | CF3 | 494.9 | 3.19 |
B44 | F | H | CF3 | Cl | 494.9 | 3.23 |
B45 | F | F | H | OCH3 | 440.5 | 2.41 |
B46 | CH3 | H | H | O-CF=CF2 | 484.5 | 3.22 |
B47 | Cl | H | H | O-CF=CF2 | 504.9 | 3.26 |
B48 | F | H | H | O-CF=CF2 | 488.5 | 3.20 |
B49 | Cl | F | H | Br | 5058 | 3.11 |
B50 | CF3 | H | Cl | H | 476.9 | 3.13 |
B51 | CF3 | F | H | H | 460.4 | 2.88 |
B52 | CF3 | F | H | Cl | 494.9 | 3.15 |
B53 | CF3 | H | CF3 | Cl | 544.9 | 3.40 |
a)用于上述方法的保留时间
b)δ[ppm](CDCl3,400MHz)
c)未测定
根据上述程序制备表D中所列式(I.B*)化合物。
表D
化合物 | R1 | R2a | R2b | R2c | MS(m/e[M+]) | HPLCa)或1H-NMRb) |
B54 | OCF3 | H | H | Cl | 492.9 | 3.16 |
B55 | CF3 | H | H | Cl | 476.9 | 3.1 |
B56 | CH3 | H | H | Cl | 422.9 | 2.93 |
B57 | F | H | H | Cl | 426.9 | 2.86 |
B58 | OCF3 | H | H | CF3 | 526.9 | 3.25 |
B59 | CF3 | H | H | CF3 | 510.5 | 3.21 |
B60 | CH3 | H | H | CF3 | 456.6 | 3.06 |
B61 | Cl | H | H | CF3 | 476.9 | 3.04 |
B62 | F | H | H | CF3 | 460.4 | 2.96 |
B63 | CF3 | H | H | CN | 467.5 | 2.70 |
B64 | CH3 | H | H | CN | 413.2 | 2.52 |
B65 | Cl | H | H | CN | 433.9 | 2.48 |
B66 | OCF3 | H | H | OCF3 | 542.5 | 3.31 |
B67 | CF3 | H | H | OCF3 | 526.5 | 3.27 |
B68 | CH3 | H | H | OCF3 | 472.5 | 3.12 |
B69 | Cl | H | H | OCF3 | 492.9 | 3.09 |
B70 | F | H | H | OCF3 | 476.4 | 3.04 |
B71 | OCF3 | Cl | H | Cl | 527.3 | n.d.c) |
B72 | CF3 | Cl | H | Cl | 511.3 | n.d.c) |
B73 | CH3 | Cl | H | Cl | 457.4 | n.d.c) |
B74 | Cl | Cl | H | Cl | 477.8 | n.d.c) |
B75 | F | Cl | H | Cl | 461.3 | n.d.c) |
B76 | OCF3 | Cl | H | Cl | 594.5 | n.d.c) |
化合物 | R1 | R2a | R2b | R2c | MS(m/e[M+]) | HPLCa)或1H-NMRb) |
B77 | CF3 | CF3 | H | CF3 | 578.5 | n.d.c) |
B78 | CH3 | CF3 | H | CF3 | 524.5 | 3.33 |
B79 | Cl | CF3 | H | CF3 | 544.9 | n.d.c) |
B80 | F | CF3 | H | CF3 | 528.4 | n.d.c) |
B81 | OCF3 | Cl | H | CF3 | 560.9 | 3.52 |
B82 | CF3 | Cl | H | CF3 | 544.9 | n.d.c) |
B83 | CH3 | Cl | H | CF3 | 490.9 | n.d.c) |
B84 | Cl | Cl | H | CF3 | 511.3 | 3.27 |
B85 | F | Cl | H | CF3 | 494.9 | 3.24 |
B86 | OCF3 | CF3 | H | H | 526.4 | n.d.c) |
B87 | CF3 | CF3 | H | H | 510.5 | 3.14 |
B88 | CH3 | CF3 | H | H | 456.5 | 3.04 |
B89 | Cl | CF3 | H | H | 476.9 | n.d.c) |
B90 | F | CF3 | H | H | 460.4 | 2.95 |
B91 | OCF3 | Cl | H | H | 492.9 | 3.16 |
B92 | CF3 | Cl | H | H | 476.9 | 3.08 |
B93 | CH3 | Cl | H | H | 422.9 | n.d.c) |
B94 | Cl | Cl | H | H | 443.4 | n.d.c) |
B95 | F | Cl | H | H | 426.9 | 2.88 |
B96 | OCF3 | CF3 | H | Cl | 560.9 | 3.44 |
B97 | CF3 | CF3 | H | Cl | 544.9 | 3.38 |
B98 | CH3 | CF3 | H | Cl | 490.9 | 3.3 |
B99 | Cl | CF3 | H | Cl | 511.3 | 3.3 |
B100 | F | CF3 | H | Cl | 494.9 | 3.21 |
B101 | OCF3 | F | H | F | 494.9 | 3.1 |
B102 | CF3 | F | H | F | 478.4 | 3.05 |
B103 | CH3 | F | H | F | 424.5 | 2.85 |
B104 | Cl | F | H | F | 444.9 | 2.83 |
B105 | F | F | H | F | 428.4 | n.d.c) |
B106 | OCF3 | F | H | H | 476.4 | 3.06 |
B107 | CF3 | F | H | H | 460.4 | 3.01 |
化合物 | R1 | R2a | R2b | R2c | MS(m/e[M+]) | HPLCa)或1H-NMRb) |
B108 | CH3 | F | H | H | 406.5 | n.d.c) |
B109 | Cl | F | H | H | 426.9 | 2.74 |
B110 | F | F | H | H | 410.4 | 2.74 |
B111 | OCF3 | H | H | CN | 483.5 | 2.78 |
B112 | CH3 | H | H | CN | 413.2 | 2.56 |
B113 | OCF3 | Cl | H | Cl | 527.3 | n.d.c) |
B114 | CF3 | Cl | H | Cl | 511.3 | 3.34 |
B115 | CH3 | Cl | H | Cl | 457.4 | 3.17 |
B116 | Cl | Cl | H | Cl | 477.8 | 3.18 |
B117 | F | Cl | H | Cl | 461.3 | 3.10 |
B118 | CF3 | Cl | H | CF3 | 544.9 | n.d.c) |
B119 | CH3 | Cl | H | CF3 | 490.93 | n.d.c) |
B120 | Cl | CF3 | H | H | 476.9 | 2.96 |
B121 | CH3 | Cl | H | H | 422.9 | 2.88 |
B122 | Cl | Cl | H | H | 443.4 | 2.88 |
B123 | F | F | H | F | 428.4 | 2.73 |
B124 | CH3 | F | H | H | 406.5 | 2.75 |
a)用于上述方法的保留时间
b)δ[ppm](CDCl3,400MHz)
c)未测定
以类似方式制备表E中所列式(I.B)的对比例。
表E
化合物 | R1 | R2a | R2b | R2c | HPLC,1H-NMR |
C1 | H | H | H | OCF3 | n.d.c) |
C2 | H | H | H | CF3 | n.d.c) |
c)未测定
II.生物学活性评价
II.1对棉蚜(Aphis gossypii)的活性,混合生命阶段
在处理之前通过将来自主蚜虫群体的重度侵染的叶子置于各子叶的顶部而将子叶阶段的棉花植株侵染。使蚜虫经过整夜转移并移走宿主叶子。然后将侵染的子叶浸入试验溶液中并搅动3秒,然后在通风橱中干燥。在25℃和20-40%相对湿度下将试验植株在荧光光照下维持24小时光照期。5天后相对于未处理对照植株上的致死率确定已处理植株上的蚜虫致死率。
在该试验中,与未处理对照相比,化合物B1、B3、B7、B12、B14、B27、B45、B56、B59、B85、B90、B115、B117和B123在300ppm下显示出至少75%的致死率。
II.2对桃蚜(Myzus persicae)的活性
将活性化合物在50∶50丙酮∶水和100ppm KineticTM表面活性剂中配制。
通过将侵染的叶片置于试验植株的顶部而将第2对叶阶段的辣椒植株(栽培品种为‘California Wonder’)用约40只实验室培养的蚜虫侵染。24小时后移走所述叶片。将完整植株的叶子浸入试验化合物的梯度溶液中并进行干燥。在约25℃和20-40%相对湿度下将试验植株维持在荧光下(24小时光照期)。5天后相对于未处理对照植株上的致死率确定已处理植株上的蚜虫致死率。
在该试验中,与未处理对照相比,化合物B1、B3、B9、B14、B27、B31、B56和B85在300ppm下显示出至少75%的致死率。
II.3对亚热带粘虫(南部灰翅夜蛾(Spodoptera eridania)),2-3龄幼虫
将活性化合物在35%丙酮和水的混合物中配制成10.000ppm溶液,需要的话将其用水稀释。
将生长至第一真叶的菜豆(Sieva lima bean)叶子浸入试验溶液中并搅动3秒钟,然后在通风橱中干燥。然后将处理的植株置于25cm有孔拉封塑料袋中,加入10只2龄幼虫并将袋密封。4天后观察致死率、植株进食和对幼虫生长的任何干扰。
在该试验中,与未处理对照相比,化合物B1、B3、B8、B10、B12、B26、B31、B32、B45、B60、B84、B90、B98和B103在300ppm下显示出至少75%的致死率。
II.4对科罗拉多马铃薯甲虫(马铃薯叶甲(Leptinotarsa decemlineata))的活性
将土豆植株用于生物鉴定。将切下的植株叶子浸入活性化合物的1∶1丙酮/水稀释液中。在叶子干燥之后,将它们分别放于陪替氏培养皿底上的水润湿滤纸上。将各培养皿用5-7只幼虫侵染并盖上盖子。每一处理稀释液重复4次。将测试培养皿保持在约27℃和60%湿度下。在处理施用5天后评价各培养皿中的活幼虫和生病幼虫数并计算致死率百分数。
在该试验中,与未处理对照相比,化合物B2、B16、B32、B68、B84、B121和B122在2500ppm下显示出至少75%的致死率。
II.5对小菜蛾(菜蛾(Plutella xylostella))的活性
将活性化合物在50∶50丙酮/水和0.1体积%Alkamuls EL 620表面活性剂中配制。将卷心菜叶子的6cm叶盘浸入试验溶液中3秒并在衬有潮湿滤纸的陪替板中风干。将叶盘用10只三龄幼虫接种并保持在25-27℃和50-60%湿度下3天。处理72小时后评价致死率。
在该试验中,与未处理对照相比,化合物B1、B3、B12、B23、B27和B115在300ppm下显示出至少75%的致死率。
II.6对二斑叶螨(二点叶螨(Tetranychus urticae),OP-抗性株)的活性
将活性化合物在50∶50丙酮∶水和100ppm KineticTM表面活性剂中配制。
通过在各植株上放置一小片取自主群体的侵染叶子(含约100只螨虫)而将主叶生长至7-12cm的菜豆(Sieva lima bean)植株侵染。这在处理之前约2小时进行以使螨虫移到测试植株上产卵。取下用于转移螨虫的叶子。将新侵染的植株浸入测试溶液中并干燥。将测试植株在约25℃和20-40%相对湿度下保持在荧光(24小时光照期)下。5天后取下一片叶子进行致死率计数。
在该试验中,与未处理对照相比,化合物B1和B7在300ppm下显示出至少75%的致死率。
II.7对稻飞虱(Nilaparvata lugens)的活性
将活性化合物配成20∶80丙酮∶水溶液。以0.1体积%的比例加入表面活性剂(Alkamuls EL 620)。
在1.7巴下使用空气驱动的手持雾化器(Devillbis雾化器)对3-4周龄的盆栽稻植株用喷雾10ml测试溶液。使已处理植株干燥约1小时并用Mylar笼子罩住。将植株用10只成虫(5雄5雌)接种并在25-27℃和50-60%湿度下保持3天。处理24、48和72小时后评价致死率。通常在水表面上发现死昆虫。各处理重复一次。
在该试验中,与未处理对照相比,化合物B16在300ppm下显示出至少75%的致死率。
II.8对墨西哥棉铃象(Anthonomus grandis)的活性
将活性化合物在1∶3DMSO/水中配制。将10-15只卵放入填充有在水中的2%琼脂和300ppm福尔马林的微量滴定板中。用20μL试验溶液喷雾所述卵,将板用穿孔箔密封并以白天/夜晚循环在24-26℃和75-85%湿度下保持3-5天。基于琼脂表面上的剩余未孵化卵或幼虫和/或由孵化的幼虫引起的挖掘通道数量和深度评价致死率。测试重复2次。
在该试验中,与未处理对照相比,化合物B68、B116和B117在2500ppm下显示出超过75%的致死率。
II.9对地中海实蝇(Ceratitis capitata)的活性
将活性化合物在1∶3DMSO/水中配制。将50-80只卵放入填充有在水中的0.5%琼脂和14%食物的微量滴定板中。用5μL试验溶液喷雾所述卵,将板用穿孔箔密封并在荧光下在27-29℃和75-85%湿度下保持6天。基于孵化的幼虫的灵活性评价致死率。试验重复2次。
在该试验中,化合物B85和B98在2500ppm下显示出超过75%的致死率。
II.10对美洲烟叶蛾(烟芽夜蛾(Heliothis virescens))的活性
将活性化合物在1∶3DMSO/水中配制。将15-25只卵放入填充有食物的微量滴定板中。用10μL试验溶液喷雾所述卵,将板用穿孔箔密封并在荧光下在27-29℃和75-85%湿度下保持6天。基于孵化的幼虫的灵活性和对比进食评价致死率。试验重复2次。
在该试验中,化合物在2500ppm下显示出至少75%的致死率。
II.11对蚕豆修尾蚜(Megoura viciae)的活性
将活性化合物在1∶3DMSO/水中配制。将豆叶盘放入填充有0.8%琼脂和2.5ppm OPUSTM的微量滴定板中。用2.5μL试验溶液喷雾叶盘并将5-8只蚜虫成虫放入微量滴定板中,然后封闭微量滴定板并在荧光下于22-24℃和35-45%下保持6天。基于活的繁殖蚜虫评价致死率。试验重复2次。
在该试验中,与未处理对照的0%致死率相比,化合物在2500ppm下显示出至少75%的致死率。
II.12对美洲烟叶蛾(烟芽夜蛾(Heliothis virescens))的活性
将两叶棉花植株用于生物鉴定。将切下的植株叶子浸入活性化合物的1∶1丙酮/水稀释液中。在叶子干燥之后,将它们分别放于陪替氏培养皿底上的水润湿滤纸上。将各培养皿用5-7只幼虫侵染并盖上盖子。每一处理稀释液重复4次。将测试培养皿保持在约27℃和60%湿度下。在处理施用5天后评价各培养皿中的活幼虫和生病幼虫数并计算致死率百分数。
II.13对银叶粉虱(Bemisia argentifolii)的活性
将活性化合物在50∶50丙酮∶水和100ppm KineticTM表面活性剂中配制。
使选取的棉花植株生长到子叶阶段(每盆一株)。将子叶浸入测试溶液中以完全覆盖叶面并放于良好通风的区域以进行干燥。将具有处理秧苗的各盆放入塑料杯中并引入10-12只粉虱成虫(约3-5天大小)。使用抽吸装置和连接于防护移液管头的0.6cm无毒Tygon管收集昆虫。然后将含有收集的昆虫的该管头轻轻地插入含有处理植株的土壤中,使昆虫爬出该管头而到达叶面上取食。将杯子用可反复使用的筛盖(150微米网目的聚酯筛PeCap,购自Tetko Inc)覆盖。将测试植株在保持室中于约25℃和20-40%相对湿度下保持3天,并避免直接暴露于荧光(24小时光照期)以防止在杯内截热。在植株处理3天后评价致死率。
在该试验中,与未处理对照相比,化合物B56、B84、B85、B115和B117在300ppm下显示出至少70%的致死率。
II.14对豇豆蚜(豆蚜(Aphis craccivora))的活性
将活性化合物在50∶50丙酮/水中配制。在记录害虫种群之后对带有100-150只不同阶段的蚜虫群体的盆栽豇豆植株喷雾。24、72和120小时后记录种群减少。
在该试验中,与未处理对照相比,化合物在300ppm下显示出至少80%的致死率。
II.15对黄热蚊(埃及伊蚊(Aedes aegypti))的活性
将试验化合物(1体积%,在丙酮中)施用于含有4龄埃及伊蚊的玻璃皿中的水中。将测试皿维持在约25℃下并每日观察致死率。各试验在3个试验皿中重复。
在该试验中,与未处理对照相比,化合物在300ppm下在6天后显示出超过90%的致死率。
II.16对黄胸散白蚁(北美散白蚁(Reticulitérmes flávipes))的活性
将毒素处理液(1.0重量%试验化合物)施用于在丙酮溶液中的4.25cm(直径)的滤纸上。基于每张滤纸的106.5mg的平均重量计算处理水平(%试验化合物)。调节处理溶液从而为在213mL丙酮中的每张滤纸提供所需的毒素量(mg)。对于未处理对照仅施用丙酮。使处理的滤纸通风以蒸发丙酮,用0.25mL水润湿并封装于带有密封盖的50×9mm陪替氏培养皿中。
在100×15mm陪替氏培养皿中进行白蚁生物鉴定,各培养皿的底上铺有10g细砂薄层。将另外2.5g砂堆积在各培养皿的侧面。将砂用2.8mL施用于堆积砂上的水润湿。在生物鉴定过程中根据需要向培养皿中加入水,以维持高水分含量。每个测试培养皿使用一张已处理滤纸(封在内部)和30只白蚁工蚁进行生物鉴定。在2个测试培养皿中重复各处理水平。将测试培养皿维持在约25℃和85%湿度下12天并每天观察致死率。
II.17对兰花蓟马(Dichromothrips corbetti)的活性
用于生物鉴定的兰花蓟马成虫由持续维持在试验室条件下的群体得到。为了测试,将测试化合物在丙酮∶水的1∶1混合物加上0.01% Kinetic表面活性剂中稀释到浓度为500ppm(化合物重量∶稀释液体积)。
各化合物的蓟马效力通过使用花浸技术评价。将塑料陪替氏培养皿用作测试场所。将各完整兰花的所有花瓣浸入处理溶液中约3秒并干燥2小时。将处理过的花与10-15只蓟马成虫一起放入各陪替氏培养皿中。然后将陪替氏培养皿用盖子盖住。在鉴定过程中将所有测试场所保持在持续光和约28℃的温度下。4天后计数各花上以及沿各陪替氏培养皿内壁的活蓟马数。由预处理蓟马数外推蓟马致死率水平。
II.18经由玻璃接触对阿根廷蚁、收获蚁、飞行蚁、木蚁、红火蚁、家蝇、厩螫蝇、肉蝇、黄热病蚊、家蚊、疟蚊、德国小蠊、猫跳蚤和棕色犬壁虱的活性
用0.5ml活性成分丙酮溶液处理玻璃小瓶(20ml闪烁小瓶)。将各小瓶不加盖滚动约10分钟以使活性成分完全涂敷小瓶并使丙酮完全干燥。将昆虫或蜱放入各小瓶中。将小瓶保持在22℃并在各时间间隔下观察处理效果。
II.19对黄曲条跳甲(Phylotretta striolata)的活性
用于生物鉴定的黄曲条跳甲由持续维持在试验室条件下的群体得到。为了测试,将测试化合物在丙酮∶水的1∶1混合物加上0.1%EL 620表面活性剂中稀释到浓度为300ppm(化合物重量∶稀释液体积)。
各化合物的活性通过使用端浸(lip-dip)技术评价。将衬有潮湿滤纸的塑料陪替氏培养皿(60×15mm)用作测试场所。将所有叶盘浸入处理溶液中约3秒并干燥2小时。将处理过的叶盘放入各陪替氏培养皿中并接种10只甲虫成虫。然后将陪替氏培养皿用盖子盖住。在鉴定过程中将所有测试场所保持在持续光和约28℃的温度下。3天后观察致死率百分数。
在该试验中,与未处理对照相比,化合物B85在300ppm下显示出至少75%的致死率。
II.20对大青叶蝉(Nephotettix virescens)的活性
用于生物鉴定的叶蝉成虫由持续维持在试验室条件下的群体得到。为了测试,将测试化合物在丙酮∶水的1∶1混合物加上0.1%EL 620表面活性剂中稀释到浓度为300ppm(化合物重量∶稀释液体积)。
叶蝉活性使用叶面喷雾施用技术评价。将盆栽稻植株(2-3周龄,栽培品种“TN-1”)在施用前清洁并干燥。所有植株使用DeVilbiss雾化器在25psi下以5ml/植株的喷雾体积在通风橱内部处理。为了确保均匀喷雾分布,将植株置于通风橱内部的旋转平台中。然后将已处理植株放入保持室内部并干燥2小时。使用Mylar笼子(4英寸直径×19英寸高度)将各植株罩住并接种10只叶蝉成虫。在鉴定过程中将所有试验植株保持在持续光和约28℃的温度下。72小时后观察致死率百分数。
在该试验中,与未处理对照相比,化合物B85在300ppm下显示出至少75%的致死率。
III.生物学活性的对比数据
本发明化合物(I)的生物学活性对比数据汇编在表F中。
表F
这些结果清楚地表明本发明化合物(I)具有提高的生物学活性。
Claims (26)
1.式(I)的喹啉化合物及其N-氧化物和盐:
其中
R1、R2各自独立地为卤素、羟基、氰基、氨基、硝基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C4烷氧基-C1-C4烷氧基、C3-C7环烷基-C1-C4烷氧基、C(OH)(CF3)2、C1-C6卤代烷基、C2-C6卤代链烯基、C1-C6卤代烷氧基、C2-C6卤代链烯氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C(Ra)=O或C(Ra)=NORb;
Ra为氢或C1-C4烷基;
Rb为氢、C1-C4烷基、C2-C4链烯基、C2-C4炔基、C1-C4卤代烷基或C2-C4卤代链烯基;
R3、R4、R5、R6各自独立地为氢、卤素、氰基、氨基、硝基、羟基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基或C(=O)ORc;
Rc为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基;
m为0、1、2、3、4或5;
n为1或2。
2.根据权利要求1的式(I)的喹啉化合物,其中n为1。
3.根据权利要求2的式(I)的喹啉化合物,其中取代基R1在相对于磺酰胺结构部分的间位连接于苯基上。
4.根据权利要求2的式(I)的喹啉化合物,其中取代基R1在相对于磺酰胺结构部分的邻位连接于苯基上。
5.根据前述权利要求中任一项的式(I)的喹啉化合物,其中R1独立地选自卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基磺酰基或C1-C6卤代烷基磺酰基。
6.根据权利要求5的式(I)的喹啉化合物,其中R1独立地选自F、Cl、Br、CH3、CHF2、CF3、OCH3、OCHF2和OCF3。
7.根据前述权利要求中任一项的式(I)的喹啉化合物,其中m为1、2或3。
8.根据前述权利要求中任一项的式(I)的喹啉化合物,其中R2独立地选自卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基磺酰基或C1-C6卤代烷基磺酰基.
9.根据权利要求8的式(I)的喹啉化合物,其中R2独立地选自F、Cl、Br、CH3、CHF2、CF3、OCH3、OCHF2和OCF3。
10.根据前述权利要求中任一项的式(I)的喹啉化合物,其中R3、R4、R5、R6各自独立地选自氢、卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基或C1-C6烷硫基。
11.根据权利要求10的式(I)的喹啉化合物,其中R3、R4、R5、R6各自为氢。
15.根据权利要求14的制备式(I)的喹啉化合物的方法,额外包括:使磺酰氯(IV)与喹啉(V)在碱存在下反应而得到式(II)化合物:
其中在上述化合物(IV)和(V)中的变量具有对式(I)的喹啉化合物所给的含义,且L1和L2为合适的离去基团。
17.如权利要求1-13中任一项所定义的式(I)化合物及其N-氧化物或盐在防治节肢动物害虫或线虫中的用途。
18.包含至少一种如权利要求1-13中任一项所定义的式(I)化合物和/或其N-氧化物或盐和载体材料的组合物。
19.一种防治节肢动物害虫或线虫的方法,包括使昆虫、蜘蛛或线虫或其食物供应源、栖息地、繁殖地或其场所与至少一种如权利要求1-13中任一项所定义的式(I)化合物和/或其N-氧化物或盐接触。
20.一种保护生长中的植物免受节肢动物害虫或线虫侵袭或侵染的方法,包括向植物或它们生长的土壤或水体中施用至少一种如权利要求1-13中任一项所定义的式(I)化合物和/或其N-氧化物或可农用盐。
21.如权利要求19或20所要求的方法,其中所述至少一种式(I)化合物和/或其N-氧化物或可农用盐按照式(I)化合物计算以5-2000g/ha的量施用。
22.一种保护种子的方法,包括使种子与至少一种如权利要求1-13中任一项所定义的式(I)化合物和/或其N-氧化物或可农用盐或以杀虫有效量包含这些化合物中的至少一种的组合物接触。
23.如权利要求22所要求的方法,其中所述至少一种式(I)化合物和/或其N-氧化物或可农用盐按照式(I)化合物计算以0.1g-10kg/100kg种子的量施用。
24.种子,包含至少一种如权利要求1-13中任一项所定义的式(I)化合物和/或其N-氧化物或可农用盐。
25.一种处理、防治、预防或保护动物免受寄生虫侵袭或侵染的方法,包括对动物给药或施用杀寄生虫有效量的至少一种如权利要求1-13中任一项所定义的式(I)化合物和/或其N-氧化物或可兽用盐。
26.协同增效杀虫混合物,包含如权利要求1-13中任一项所定义的式(I)化合物和/或其N-氧化物或盐和选自如下的杀虫剂:有机(硫代)磷酸酯,氨基甲酸酯,拟除虫菊酯,生长调节剂,新烟碱,烟酸受体激动剂/拮抗剂化合物,GABA拮抗剂化合物,大环内酯杀虫剂,METI I、II和III化合物,氧化磷酸化抑制剂化合物,蜕皮干扰剂化合物,混合功能氧化酶抑制剂化合物,钠通道阻断剂化合物,benclothiaz,联苯肼酯,杀螟丹,氟啶虫酰胺,啶虫丙醚,拒嗪酮,硫,硫环杀,氟虫酰胺,cyanopyrafen,吡氟硫磷,丁氟螨酯,amidoflumet,邻氨基苯甲酰胺和N-R′-2,2-二halo-1-R″-环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙或N-R′-2,2-二(R″′)-丙酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙,其中R′为甲基或乙基,halo为氯或溴,R″为氢或甲基且R″′为甲基或乙基。
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CN103958476A (zh) * | 2011-11-28 | 2014-07-30 | 纳幕尔杜邦公司 | N-(4-喹啉基甲基)磺酰胺衍生物以及它们作为驱肠虫剂的用途 |
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CN103958476A (zh) * | 2011-11-28 | 2014-07-30 | 纳幕尔杜邦公司 | N-(4-喹啉基甲基)磺酰胺衍生物以及它们作为驱肠虫剂的用途 |
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