CN101141878A - 联苯-n-(4-吡啶基)甲基磺酰胺 - Google Patents
联苯-n-(4-吡啶基)甲基磺酰胺 Download PDFInfo
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- CN101141878A CN101141878A CNA2006800085874A CN200680008587A CN101141878A CN 101141878 A CN101141878 A CN 101141878A CN A2006800085874 A CNA2006800085874 A CN A2006800085874A CN 200680008587 A CN200680008587 A CN 200680008587A CN 101141878 A CN101141878 A CN 101141878A
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- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical class N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
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- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- WHMZYGMQWIBNOC-UHFFFAOYSA-N propan-2-yl n-(3,4-dimethoxyphenyl)carbamate Chemical compound COC1=CC=C(NC(=O)OC(C)C)C=C1OC WHMZYGMQWIBNOC-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- WXQDLXGLMTUUKH-UHFFFAOYSA-N pyridin-4-ylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=NC=C1 WXQDLXGLMTUUKH-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
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- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
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- 208000005687 scabies Diseases 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- 229930185156 spinosyn Natural products 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
- 238000007592 spray painting technique Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003447 sulfenic acid derivatives Chemical class 0.000 description 1
- CCEKAJIANROZEO-UHFFFAOYSA-N sulfluramid Chemical compound CCNS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CCEKAJIANROZEO-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 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
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
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Abstract
本发明涉及式(I)的联苯磺酰胺以及化合物I的N-氧化物、可农用盐和可兽用盐,制备这些化合物的方法,包含它们的组合物,它们在防治植物病原性有害真菌和有害节肢动物中的用途,对抗节肢动物门害虫的方法,保护作物以防节肢动物侵袭或侵染的方法,保护种子和非活体材料以防节肢动物门害虫侵染的方法,保护非活体材料以防节肢动物门害虫侵袭或侵染的方法以及包含化合物I的种子。
Description
本发明涉及式I的联苯磺酰胺以及化合物I的N-氧化物、可农用盐和可兽用盐:
其中各取代基如下所定义:
R1为氢、C1-C4烷基、C1-C4烷氧基、C2-C4链烯基、C2-C4炔基或苄基;R2、R3、R4、R5相互独立地为氢、卤素、C1-C4烷基、卤代甲基、C1-C4烷氧基、卤代甲氧基、C1-C4烷硫基、C1-C4烷基氨基或二(C1-C4烷基)氨基;
R6、R7相互独立地为氢、羟基、氰基、硝基、氨基、卤素、C1-C8烷基、C1-C6卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C6烷硫基、(C1-C4烷基)羰基、(C1-C4烷氧基)羰基、-C(R8)=NOR9、C1-C4烷基氨基、二(C1-C4烷基)氨基、(C1-C4烷基)氨基羰基、二(C1-C4烷基)氨基羰基、苯基或苯氧基,其中所述环可以带有1-3个基团R10,
或者
两个基团R6或两个基团R7与它们所连接的苯基环的两个相邻环成员一起可以形成稠合环戊基、环己基或苯基环,其中这些稠合环本身可以带有1或2个基团R10;
R10为卤素、氰基、硝基、C1-C4烷基、C1-C4烷氧基、卤代甲基或卤代甲氧基;
R8为C1-C4烷基;
R9为C1-C8烷基、C1-C4卤代烷基、C2-C4链烯基、C2-C4卤代链烯基、C2-C4炔基、C2-C4卤代炔基或苄基;
m为0、1、2、3或4;
n为0、1、2、3、4或5;
条件是若R2、R3、R4和R5都为氢,则m和n不同时为0。
此外,本发明涉及制备这些化合物的方法、包含它们的组合物以及它们在防治植物病原性有害真菌中的用途。
本发明还涉及联苯磺酰胺I在对抗节肢动物门害虫(有害节肢动物)和保护材料以防被所述害虫侵染和/或破坏中的用途。
WO 2005/033081描述了各种吡啶基磺酰胺。EP-A 206581和Lieb.Ann.Chem.641(1990)描述了各种4-吡啶甲基磺酰胺。所提到的这些出版物中所述的化合物适于防治有害真菌。
本发明化合物与WO 2005/033081中所述那些的不同在于联苯基的取代方式。
然而,在许多情况下,它们的作用并不令人满意。基于此,本发明的目的是提供具有改进的作用和/或拓宽的活性谱的化合物。
我们发现该目的由开头所定义的化合物实现。此外,我们还发现了制备它们的方法和中间体,包含它们的组合物和使用化合物I防治有害真菌的方法。
与已知化合物相比,式I化合物对有害真菌具有增加的效力。
惊人的是,化合物I、其N-氧化物和盐还适于防治节肢动物门害虫,尤其是对抗昆虫。
同样,化合物I、其N-氧化物和盐还可用于对抗蜘蛛纲。
本文所用术语“对抗”包括防治,即杀灭害虫以及保护植物、非活体材料或种子以免被所述害虫侵袭或侵染。
因此,本发明还提供了用于对抗该类害虫的组合物,其优选呈可直接喷雾溶液、乳液、糊、油分散体、粉末、撒播用材料、粉剂形式,或呈颗粒形式,所述组合物包含杀虫有效量的至少一种式I化合物或至少一种其N-氧化物或盐和至少一种可以为液体和/或固体且优选可农用的载体和/或至少一种表面活性剂。
此外,本发明提供了一种对抗该类害虫的方法,包括使所述害虫,其栖息地,繁殖地,食物源,动物害虫生长或可能生长于其中的植物、种子、土壤、区域、材料或环境或需要防止所述害虫侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的本文所定义的式I化合物或其N-氧化物或盐接触。
本发明尤其提供了一种保护包括种子在内的作物以防止节肢动物门害虫侵袭或侵染的方法,所述方法包括使作物与杀虫有效量的至少一种本文所定义的式I化合物或其N-氧化物或盐接触。
本发明还提供了一种保护非活体材料以防止上述害虫侵袭或侵染的方法,该方法包括使非活体材料与杀虫有效量的至少一种本文所定义的式I化合物或其N-氧化物或盐接触。
合适的式I化合物包括可能存在的所有可能立体异构体(顺式/反式异构体、对映体)及其混合物。立体异构中心例如为-C(R8)=NOR9结构部分的碳和氮原子以及基团R1、R2、R3、R4和/或R5等中的不对称碳原子。本发明提供了纯对映体或非对映体或其混合物,纯顺式-和反式-异构体及其混合物。通式I的化合物还可能以不同的互变异构体形式存在。本发明包括单一的互变异构体(若可分离的话)以及互变异构体混合物。
式I化合物可以其生物活性上不同的各种晶型存在。它们也构成本发明主题的一部分。
式I化合物的盐优选为可农用盐。它们可以常规方法形成,例如在式I化合物具有碱性官能团时通过使该化合物与所述阴离子的酸反应,或使式I的酸性化合物与合适的碱反应。
合适的可农用盐尤其是其阳离子和阴离子分别对本发明化合物的作用没有任何不利影响的那些阳离子的盐或那些酸的酸加成盐。合适的阳离子尤其是碱金属离子,优选锂、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;还有铵离子(NH4 +)和其中1-4个氢原子被C1-C4烷基、C1-C4羟基烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、羟基-C1-C4烷氧基-C1-C4烷基、苯基或苄基代替的取代铵离子。取代铵离子的实例包括甲基铵、异丙基铵、二甲基铵、二异丙基铵、三甲基铵、四甲基铵、四乙基铵、四丁基铵、2-羟基乙基铵、2-(2-羟基乙氧基)乙基铵、二(2-羟基乙基)铵、苄基三甲基铵和苄基三乙基铵,此外还有离子,锍离子,优选三(C1-C4烷基)锍和氧化锍离子,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、苯甲酸根和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Ia和Ib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。
在各变量的上述定义中提到的有机结构部分象术语卤素一样是各所列基团成员的集合性术语。前缀Cn-Cm在每种情况下表示该基团中的可能碳原子数。
卤素:氟、氯、溴和碘;
烷基以及烷基羰基、烷基氨基、二烷基氨基、烷基氨基羰基、二烷基氨基羰基中的所有烷基结构部分:具有1-4、1-6或1-8个碳原子的饱和直链或支化烃基,例如C1-C6烷基,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;
卤代烷基:具有1-2或1-4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:尤其是C1-C2卤代烷基,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、二氯氟甲基、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、五氟乙基或1,1,1-三氟丙-2-基;
链烯基:具有2-4、2-6或2-8个碳原子和一个或两个在任意位置的双键的不饱和直链或支化烃基,例如C2-C6链烯基,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;
卤代链烯基:具有2-6个碳原子和一个或两个在任意位置的双键的不饱和直链或支化烃基(如上所述),其中在这些基团中部分或所有氢原子可以被上述卤原子代替,尤其被氟、氯和溴代替;
炔基:具有2-4、2-6或2-8个碳原子和一个或两个在任意位置的叁键的直链或支化烃基,例如C2-C6炔基,如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、3-甲基-1-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-1-戊炔基、3-甲基-4-戊炔基、4-甲基-1-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基;
卤代炔基:具有2-4个碳原子和一个在任意位置的叁键的不饱和直链或支化烃基(如上所述),其中在这些基团中部分或所有氢原子可以被上述卤原子代替,尤其被氟、氯和/或溴代替;
含有1-4个选自O、N和S的杂原子的5-10员饱和、部分不饱和或芳族杂环:
-含有1-3个氮原子和/或1个氧或硫原子或1或2个氧和/或硫原子的5或6员杂环基,例如2-四氢呋喃基、3-四氢呋喃基、2-四氢噻吩基、3-四氢噻吩基、2-吡咯烷基、3-吡咯烷基、3-异唑烷基、4-异唑烷基、5-异唑烷基、3-异噻唑烷基、4-异噻唑烷基、5-异噻唑烷基、3-吡唑烷基、4-吡唑烷基、5-吡唑烷基、2-唑烷基、4-唑烷基、5-唑烷基、2-噻唑烷基、4-噻唑烷基、5-噻唑烷基、2-咪唑烷基、4-咪唑烷基、2-吡咯烷-2-基、2-吡咯烷-3-基、3-吡咯烷-2-基、3-吡咯烷-3-基、2-哌啶基、3-哌啶基、4-哌啶基、1,3-二烷-5-基、2-四氢吡喃基、4-四氢吡喃基、2-四氢噻吩基、3-六氢哒嗪基、4-六氢哒嗪基、2-六氢嘧啶基、4-六氢嘧啶基、5-六氢嘧啶基和2-哌嗪基;
-含有1-4个氮原子或1-3个氮原子和1个硫或氧原子的5员杂芳基:除了碳原子外还可以含有1-4个氮原子或1-3个氮原子和1个硫或氧原子作为环成员的5员杂芳基,例如2-噻吩基、3-噻吩基、3-吡唑基、4-吡唑基、5-吡唑基、2-唑基、4-唑基、5-唑基、2-噻唑基、4-噻唑基、5-噻唑基、2-咪唑基、4-咪唑基和1,3,4-三唑-2-基;
-含有1-3个或1-4个氮原子的6员杂芳基:除了碳原子外还可以含有1-3个或1-4个氮原子作为环成员的6员杂芳基,例如2-吡啶基、3-吡啶基、4-吡啶基、3-哒嗪基、4-哒嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基和2-吡嗪基。
本发明的范围包括具有手性中心的式I化合物的(R)-和(S)-异构体以及外消旋体。
考虑到式I的联苯磺酰胺的意欲用途,特别优选取代基的下列含义,在每种情况下单独或组合:
本发明优选提供其中R1为氢或甲基,尤其是氢的式I化合物。
还优选其中R2、R3、R4和R5相互独立地为氢、甲基、乙基、氟、氯、CF3、OCH3、OC2H5、OCHF2、OCF3、SCH3或SC2H5,或尤其是氢的式I化合物。
此外,还优选其中至少一个,尤其是一个或两个选自R2、R3、R4和R5的基团不为氢的式I化合物。此时所述基团优选为氯、甲基或甲氧基。
就此而言,优选其中R2和R5为氢的化合物I。
同样优选其中R4和R5为氢的化合物I。
同样优选被两个相同的选自R2、R3、R4和R5的基团取代的式I化合物。
R6优选为卤素,尤其是氯和氟;C1-C4烷基,尤其是甲基和乙基;C1-C4烷氧基,尤其是甲氧基和乙氧基;C1-C4卤代烷基,尤其是三氟甲基;C1-C4卤代烷氧基,尤其是二氟甲氧基和三氟甲氧基;C1-C4硫代烷基,尤其是硫代甲基;(C1-C4烷氧基)羰基,尤其是甲氧羰基或乙氧羰基。
特别优选其中R6为卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基的化合物I。
R7优选为卤素,尤其是氯和氟;C1-C8烷基,尤其是甲基、乙基、异丙基、叔丁基;C1-C8烷氧基,尤其是甲氧基、乙氧基、异丙氧基、叔丁氧基;C1-C4卤代烷基,尤其是三氟甲基和五氟乙基;C1-C8硫代烷基,尤其是硫代甲基和硫代乙基;C(R8)=NOR9,其中R8优选为C1-C4烷基,尤其是甲基和乙基,且R9优选为C1-C6烷基、烯丙基、炔丙基和苄基;(C1-C8烷氧基)羰基,尤其是甲氧羰基和乙氧羰基;(C1-C8烷基)羰基,尤其是甲基羰基和乙基羰基;(C1-C8烷基)氨基羰基;二(C1-C8烷基)氨基羰基;以及苯基,其可以被如下基团取代:卤素,如氯或氟,C1-C4烷基,如甲基和乙基;C1-C4烷氧基,如甲氧基和乙氧基;或卤代甲基,如三氟甲基。
特别优选其中R7为卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基,尤其是氟、氯、甲基、卤代甲基、甲氧基或卤代甲氧基的化合物I。
还优选其中一个R7位于各苯基环的对位的化合物I。
式I的其他优选实施方案在每种情况下本身为式I.1-I.5化合物,其中各变量如对式I所定义:
在本发明化合物的另一优选实施方案中,指数m为0。
在本发明化合物的另一优选实施方案中,指数n为0。
在本发明化合物的另一优选实施方案中,指数n为1-5,尤其是2-5。
在本发明化合物的一个实施方案中,一个R6位于磺酰基的邻位;这些化合物对应于式IA:
在本发明化合物的另一实施方案中,一个R6位于磺酰基的间位;这些化合物对应于式IB:
在本发明化合物的其他优选实施方案中,一个基团R7位于4位(式IC),2位(式ID),两个相同或不同的基团R7位于2,4位(式IE)或3,4位(式IF)或2,5位(式IG)。
特别优选式IC化合物。
此外,还优选式ID化合物。
尤其考虑到它们的用途,优选汇编在下表中的化合物I。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R1、R2、R3、R4和R5为氢且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的一行的式I化合物
表2
其中R1为甲基,R2、R3、R4和R5为氢且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的一行的式I化合物
表3
其中R1为氢,R2和R3为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.1化合物
表4
其中R1、R2和R3为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.1化合物
表5
其中R1为氢,R2和R3为氟且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.1化合物
表6
其中R1为氢,R2和R3为氯且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.1化合物
表7
其中R1为氢,R2和R3为甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.1化合物
表8
其中R1为氢,R2和R3为三氟甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.1化合物
表9
其中R1为氢,R2和R3为三氟甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.1化合物
表10
其中R1为氢,R3和R5为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.2化合物
表11
其中R1为氢,R3和R5为氟且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.2化合物
表12
其中R1为氢,R3和R5为氯且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.2化合物
表13
其中R1为氢,R3和R5为甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.2化合物
表14
其中R1为氢,R3和R5为三氟甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.2化合物
表15
其中R1为氢,R3和R5为三氟甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.2化合物
表16
其中R1为氢,R2和R4为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.3化合物
表17
其中R1为氢,R2和R4为氟且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.3化合物
表18
其中R1为氢,R2和R4为氯且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.3化合物
表19
其中R1为氢,R2和R4为甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.3化合物
表20
其中R1为氢,R2和R4为三氟甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.3化合物
表21
其中R1为氢,R2和R4为三氟甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.3化合物
表22
其中R1为氢,R2为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表23
其中R1和R2为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表24
其中R1为氢,R2为氟且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表25
其中R1为甲基,R2为氟且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表26
其中R1为氢,R2为氯且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表27
其中R1为甲基,R2为氯且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表28
其中R1为氢,R2为甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表29
其中R1为甲基,R2为甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表30
其中R1为氢,R2为乙氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表31
其中R1为氢,R2为三氟甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表32
其中R1为甲基,R2为三氟甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表33
其中R1为氢,R2为三氟甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表34
其中R1为甲基,R2为三氟甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.4化合物
表35
其中R1为氢,R3为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表36
其中R1为甲基,R3为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表37
其中R1为氢,R3为氟且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表38
其中R1为甲基,R3为氟且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表39
其中R1为氢,R3为氯且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表40
其中R1为甲基,R3为氯且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表41
其中R1为氢,R3为甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表42
其中R1为甲基,R3为甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表43
其中R1为氢,R3为乙氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表44
其中R1为氢,R3为三氟甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表45
其中R1为甲基,R3为三氟甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表46
其中R1为氢,R3为三氟甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表47
其中R1为甲基,R3为三氟甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.5化合物
表48
其中R1为氢,R2和R5为甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.6化合物
表49
其中R1为氢,R2和R5为氟且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.6化合物
表50
其中R1为氢,R2和R5为氯且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.6化合物
表51
其中R1为氢,R2和R5为甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.6化合物
表52
其中R1为氢,R2和R5为三氟甲氧基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.6化合物
表53
其中R1为氢,R2和R5为三氟甲基且(R6)m和(R7)n的组合对化合物而言在每种情况下对应于表A的第A-1至A-879行之一的式I.6化合物
表A
序号 | (R6)m | (R7)n |
A-1 | 2-F | - |
A-2 | 2-Cl | - |
A-3 | 2-CH3 | - |
A-4 | 2-CF3 | - |
A-5 | 2-OCH3 | - |
A-6 | 3-F | - |
A-7 | 3-Cl | - |
A-8 | 3-CH3 | - |
A-9 | 3-CF3 | - |
A-10 | 3-OCH3 | - |
A-11 | - | 2-CH3 |
A-12 | 2-F | 2-CH3 |
A-13 | 2-Cl | 2-CH3 |
A-14 | 2-CH3 | 2-CH3 |
A-15 | 2-CF3 | 2-CH3 |
A-16 | 2-OCH3 | 2-CH3 |
A-17 | 3-F | 2-CH3 |
A-18 | 3-Cl | 2-CH3 |
A-19 | 3-CH3 | 2-CH3 |
A-20 | 3-CF3 | 2-CH3 |
A-21 | 3-OCH3 | 2-CH3 |
A-22 | - | 2-CH2CH3 |
A-23 | 2-F | 2-CH2CH3 |
A-24 | 2-Cl | 2-CH2CH3 |
A-25 | 2-CH3 | 2-CH2CH3 |
序号 | (R6)m | (R7)n |
A-26 | 2-CF3 | 2-CH2CH3 |
A-27 | 2-OCH3 | 2-CH2CH3 |
A-28 | 3-F | 2-CH2CH3 |
A-29 | 3-Cl | 2-CH2CH3 |
A-30 | 3-CH3 | 2-CH2CH3 |
A-31 | 3-CF3 | 2-CH2CH3 |
A-32 | 3-OCH3 | 2-CH2CH3 |
A-33 | - | 2-Br |
A-34 | 2-F | 2-Br |
A-35 | 2-Cl | 2-Br |
A-36 | 2-CH3 | 2-Br |
A-37 | 2-CF3 | 2-Br |
A-38 | 2-OCH3 | 2-Br |
A-39 | 3-F | 2-Br |
A-40 | 3-Cl | 2-Br |
A-41 | 3-CH3 | 2-Br |
A-42 | 3-CF3 | 2-Br |
A-43 | 3-OCH3 | 2-Br |
A-44 | - | 2-Cl |
A-45 | 2-F | 2-Cl |
A-46 | 2-Cl | 2-Cl |
A-47 | 2-CH3 | 2-Cl |
A-48 | 2-CF3 | 2-Cl |
A-49 | 2-OCH3 | 2-Cl |
A-50 | 3-F | 2-Cl |
A-51 | 3-Cl | 2-Cl |
A-52 | 3-CH3 | 2-Cl |
A-53 | 3-CF3 | 2-Cl |
A-54 | 3-OCH3 | 2-Cl |
A-55 | - | 2-F |
A-56 | 2-F | 2-F |
A-57 | 2-Cl | 2-F |
序号 | (R6)m | (R7)n |
A-58 | 2-CH3 | 2-F |
A-59 | 2-CF3 | 2-F |
A-60 | 2-OCH3 | 2-F |
A-61 | 3-F | 2-F |
A-62 | 3-Cl | 2-F |
A-63 | 3-CH3 | 2-F |
A-64 | 3-CF3 | 2-F |
A-65 | 3-OCH3 | 2-F |
A-66 | - | 2-CN |
A-67 | 2-F | 2-CN |
A-68 | 2-Cl | 2-CN |
A-69 | 2-CH3 | 2-CN |
A-70 | 2-CF3 | 2-CN |
A-71 | 2-OCH3 | 2-CN |
A-72 | 3-F | 2-CN |
A-73 | 3-Cl | 2-CN |
A-74 | 3-CH3 | 2-CN |
A-75 | 3-CF3 | 2-CN |
A-76 | 3-OCH3 | 2-CN |
A-77 | - | 2-NO2 |
A-78 | 2-F | 2-NO2 |
A-79 | 2-Cl | 2-NO2 |
A-80 | 2-CH3 | 2-NO2 |
A-81 | 2-CF3 | 2-NO2 |
A-82 | 2-OCH3 | 2-NO2 |
A-83 | 3-F | 2-NO2 |
A-84 | 3-Cl | 2-NO2 |
A-85 | 3-CH3 | 2-NO2 |
A-86 | 3-CF3 | 2-NO2 |
A-87 | 3-OCH3 | 2-NO2 |
A-88 | - | 2-OCH3 |
A-89 | 2-F | 2-OCH3 |
序号 | (R6)m | (R7)n |
A-90 | 2-Cl | 2-OCH3 |
A-91 | 2-CH3 | 2-OCH3 |
A-92 | 2-CF3 | 2-OCH3 |
A-93 | 2-OCH3 | 2-OCH3 |
A-94 | 3-F | 2-OCH3 |
A-95 | 3-Cl | 2-OCH3 |
A-96 | 3-CH3 | 2-OCH3 |
A-97 | 3-CF3 | 2-OCH3 |
A-98 | 3-OCH3 | 2-OCH3 |
A-99 | - | 2-CF3 |
A-100 | 2-F | 2-CF3 |
A-101 | 2-Cl | 2-CF3 |
A-102 | 2-CH3 | 2-CF3 |
A-103 | 2-CF3 | 2-CF3 |
A-104 | 2-OCH3 | 2-CF3 |
A-105 | 3-F | 2-CF3 |
A-106 | 3-Cl | 2-CF3 |
A-107 | 3-CH3 | 2-CF3 |
A-108 | 3-CF3 | 2-CF3 |
A-109 | 3-OCH3 | 2-CF3 |
A-110 | H | 2-SCH3 |
A-111 | 2-F | 2-SCH3 |
A-112 | 2-Cl | 2-SCH3 |
A-113 | 2-CH3 | 2-SCH3 |
A-114 | 2-CF3 | 2-SCH3 |
A-115 | 2-OCH3 | 2-SCH3 |
A-116 | 3-F | 2-SCH3 |
A-117 | 3-Cl | 2-SCH3 |
A-118 | 3-CH3 | 2-SCH3 |
A-119 | 3-CF3 | 2-SCH3 |
A-120 | 3-OCH3 | 2-SCH3 |
A-121 | - | 2-C(=O)CH3 |
序号 | (R6)m | (R7)n |
A-122 | 2-F | 2-C(=O)CH3 |
A-123 | 2-Cl | 2-C(=O)CH3 |
A-124 | 2-CH3 | 2-C(=O)CH3 |
A-125 | 2-CF3 | 2-C(=O)CH3 |
A-126 | 2-OCH3 | 2-C(=O)CH3 |
A-127 | 3-F | 2-C(=O)CH3 |
A-128 | 3-Cl | 2-C(=O)CH3 |
A-129 | 3-CH3 | 2-C(=O)CH3 |
A-130 | 3-CF3 | 2-C(=O)CH3 |
A-131 | 3-OCH3 | 2-C(=O)CH3 |
A-132 | - | 2-C(=NOCH3)CH3 |
A-133 | 2-F | 2-C(=NOCH3)CH3 |
A-134 | 2-Cl | 2-C(=NOCH3)CH3 |
A-135 | 2-CH3 | 2-C(=NOCH3)CH3 |
A-136 | 2-CF3 | 2-C(=NOCH3)CH3 |
A-137 | 2-OCH3 | 2-C(=NOCH3)CH3 |
A-138 | 3-F | 2-C(=NOCH3)CH3 |
A-139 | 3-Cl | 2-C(=NOCH3)CH3 |
A-140 | 3-CH3 | 2-C(=NOCH3)CH3 |
A-141 | 3-CF3 | 2-C(=NOCH3)CH3 |
A-142 | 3-OCH3 | 2-C(=NOCH3)CH3 |
A-143 | - | 3-CH3 |
A-144 | 2-F | 3-CH3 |
A-145 | 2-Cl | 3-CH3 |
A-146 | 2-CH3 | 3-CH3 |
A-147 | 2-CF3 | 3-CH3 |
A-148 | 2-OCH3 | 3-CH3 |
A-149 | 3-F | 3-CH3 |
A-150 | 3-Cl | 3-CH3 |
A-151 | 3-CH3 | 3-CH3 |
A-152 | 3-CF3 | 3-CH3 |
A-153 | 3-OCH3 | 3-CH3 |
序号 | (R6)m | (R7)n |
A-154 | - | 3-CH2CH3 |
A-155 | 2-F | 3-CH2CH3 |
A-156 | 2-Cl | 3-CH2CH3 |
A-157 | 2-CH3 | 3-CH2CH3 |
A-158 | 2-CF3 | 3-CH2CH3 |
A-159 | 2-OCH3 | 3-CH2CH3 |
A-160 | 3-F | 3-CH2CH3 |
A-161 | 3-Cl | 3-CH2CH3 |
A-162 | 3-CH3 | 3-CH2CH3 |
A-163 | 3-CF3 | 3-CH2CH3 |
A-164 | 3-OCH3 | 3-CH2CH3 |
A-165 | - | 3-Br |
A-166 | 2-F | 3-Br |
A-167 | 2-Cl | 3-Br |
A-168 | 2-CH3 | 3-Br |
A-169 | 2-CF3 | 3-Br |
A-170 | 2-OCH3 | 3-Br |
A-171 | 3-F | 3-Br |
A-172 | 3-Cl | 3-Br |
A-173 | 3-CH3 | 3-Br |
A-174 | 3-CF3 | 3-Br |
A-175 | 3-OCH3 | 3-Br |
A-176 | - | 3-Cl |
A-177 | 2-F | 3-Cl |
A-178 | 2-Cl | 3-Cl |
A-179 | 2-CH3 | 3-Cl |
A-180 | 2-CF3 | 3-Cl |
A-181 | 2-OCH3 | 3-Cl |
A-182 | 3-F | 3-Cl |
A-183 | 3-Cl | 3-Cl |
A-184 | 3-CH3 | 3-Cl |
A-185 | 3-CF3 | 3-Cl |
序号 | (R6)m | (R7)n |
A-186 | 3-OCH3 | 3-Cl |
A-187 | - | 3-F |
A-188 | 2-F | 3-F |
A-189 | 2-Cl | 3-F |
A-190 | 2-CH3 | 3-F |
A-191 | 2-CF3 | 3-F |
A-192 | 2-OCH3 | 3-F |
A-193 | 3-F | 3-F |
A-194 | 3-Cl | 3-F |
A-195 | 3-CH3 | 3-F |
A-196 | 3-CF3 | 3-F |
A-197 | 3-OCH3 | 3-F |
A-198 | - | 3-CN |
A-199 | 2-F | 3-CN |
A-200 | 2-Cl | 3-CN |
A-201 | 2-CH3 | 3-CN |
A-202 | 2-CF3 | 3-CN |
A-203 | 2-OCH3 | 3-CN |
A-204 | 3-F | 3-CN |
A-205 | 3-Cl | 3-CN |
A-206 | 3-CH3 | 3-CN |
A-207 | 3-CF3 | 3-CN |
A-208 | 3-OCH3 | 3-CN |
A-209 | - | 3-NO2 |
A-210 | 2-F | 3-NO2 |
A-211 | 2-Cl | 3-NO2 |
A-212 | 2-CH3 | 3-NO2 |
A-213 | 2-CF3 | 3-NO2 |
A-214 | 2-OCH3 | 3-NO2 |
A-215 | 3-F | 3-NO2 |
A-216 | 3-Cl | 3-NO2 |
A-217 | 3-CH3 | 3-NO2 |
序号 | (R6)m | (R7)n |
A-218 | 3-CF3 | 3-NO2 |
A-219 | 3-OCH3 | 3-NO2 |
A-220 | - | 3-OCH3 |
A-221 | 2-F | 3-OCH3 |
A-222 | 2-Cl | 3-OCH3 |
A-223 | 2-CH3 | 3-OCH3 |
A-224 | 2-CF3 | 3-OCH3 |
A-225 | 2-OCH3 | 3-OCH3 |
A-226 | 3-F | 3-OCH3 |
A-227 | 3-Cl | 3-OCH3 |
A-228 | 3-CH3 | 3-OCH3 |
A-229 | 3-CF3 | 3-OCH3 |
A-230 | 3-OCH3 | 3-OCH3 |
A-231 | - | 3-CF3 |
A-232 | 2-F | 3-CF3 |
A-233 | 2-Cl | 3-CF3 |
A-234 | 2-CH3 | 3-CF3 |
A-235 | 2-CF3 | 3-CF3 |
A-236 | 2-OCH3 | 3-CF3 |
A-237 | 3-F | 3-CF3 |
A-238 | 3-Cl | 3-CF3 |
A-239 | 3-CH3 | 3-CF3 |
A-240 | 3-CF3 | 3-CF3 |
A-241 | 3-OCH3 | 3-CF3 |
A-242 | - | 3-SCH3 |
A-243 | 2-F | 3-SCH3 |
A-244 | 2-Cl | 3-SCH3 |
A-245 | 2-CH3 | 3-SCH3 |
A-246 | 2-CF3 | 3-SCH3 |
A-247 | 2-OCH3 | 3-SCH3 |
A-248 | 3-F | 3-SCH3 |
A-249 | 3-Cl | 3-SCH3 |
序号 | (R6)m | (R7)n |
A-250 | 3-CH3 | 3-SCH3 |
A-251 | 3-CF3 | 3-SCH3 |
A-252 | 3-OCH3 | 3-SCH3 |
A-253 | - | 3-C(=O)CH3 |
A-254 | 2-F | 3-C(=O)CH3 |
A-255 | 2-Cl | 3-C(=O)CH3 |
A-256 | 2-CH3 | 3-C(=O)CH3 |
A-257 | 2-CF3 | 3-C(=O)CH3 |
A-258 | 2-OCH3 | 3-C(=O)CH3 |
A-259 | 3-F | 3-C(=O)CH3 |
A-260 | 3-Cl | 3-C(=O)CH3 |
A-261 | 3-CH3 | 3-C(=O)CH3 |
A-262 | 3-CF3 | 3-C(=O)CH3 |
A-263 | 3-OCH3 | 3-C(=O)CH3 |
A-264 | - | 3-C(=NOCH3)CH3 |
A-265 | 2-F | 3-C(=NOCH3)CH3 |
A-266 | 2-Cl | 3-C(=NOCH3)CH3 |
A-267 | 2-CH3 | 3-C(=NOCH3)CH3 |
A-268 | 2-CF3 | 3-C(=NOCH3)CH3 |
A-269 | 2-OCH3 | 3-C(=NOCH3)CH3 |
A-270 | 3-F | 3-C(=NOCH3)CH3 |
A-271 | 3-Cl | 3-C(=NOCH3)CH3 |
A-272 | 3-CH3 | 3-C(=NOCH3)CH3 |
A-273 | 3-CF3 | 3-C(=NOCH3)CH3 |
A-274 | 3-OCH3 | 3-C(=NOCH3)CH3 |
A-275 | - | 4-CH3 |
A-276 | 2-F | 4-CH3 |
A-277 | 2-Cl | 4-CH3 |
A-278 | 2-CH3 | 4-CH3 |
A-279 | 2-CF3 | 4-CH3 |
A-280 | 2-OCH3 | 4-CH3 |
A-281 | 3-F | 4-CH3 |
序号 | (R6)m | (R7)n |
A-282 | 3-Cl | 4-CH3 |
A-283 | 3-CH3 | 4-CH3 |
A-284 | 3-CF3 | 4-CH3 |
A-285 | 3-OCH3 | 4-CH3 |
A-286 | - | 4-CH2CH3 |
A-287 | 2-F | 4-CH2CH3 |
A-288 | 2-Cl | 4-CH2CH3 |
A-289 | 2-CH3 | 4-CH2CH3 |
A-290 | 2-CF3 | 4-CH2CH3 |
A-291 | 2-OCH3 | 4-CH2CH3 |
A-292 | 3-F | 4-CH2CH3 |
A-293 | 3-Cl | 4-CH2CH3 |
A-294 | 3-CH3 | 4-CH2CH3 |
A-295 | 3-CF3 | 4-CH2CH3 |
A-296 | 3-OCH3 | 4-CH2CH3 |
A-297 | - | 4-Br |
A-298 | 2-F | 4-Br |
A-299 | 2-Cl | 4-Br |
A-300 | 2-CH3 | 4-Br |
A-301 | 2-CF3 | 4-Br |
A-302 | 2-OCH3 | 4-Br |
A-303 | 3-F | 4-Br |
A-304 | 3-Cl | 4-Br |
A-305 | 3-CH3 | 4-Br |
A-306 | 3-CF3 | 4-Br |
A-307 | 3-OCH3 | 4-Br |
A-308 | - | 4-Cl |
A-309 | 2-F | 4-Cl |
A-310 | 2-Cl | 4-Cl |
A-311 | 2-CH3 | 4-Cl |
A-312 | 2-CF3 | 4-Cl |
A-313 | 2-OCH3 | 4-Cl |
序号 | (R6)m | (R7)n |
A-314 | 3-F | 4-Cl |
A-315 | 3-Cl | 4-Cl |
A-316 | 3-CH3 | 4-Cl |
A-317 | 3-CF3 | 4-Cl |
A-318 | 3-OCH3 | 4-Cl |
A-319 | - | 4-F |
A-320 | 2-F | 4-F |
A-321 | 2-Cl | 4-F |
A-322 | 2-CH3 | 4-F |
A-323 | 2-CF3 | 4-F |
A-324 | 2-OCH3 | 4-F |
A-325 | 3-F | 4-F |
A-326 | 3-Cl | 4-F |
A-327 | 3-CH3 | 4-F |
A-328 | 3-CF3 | 4-F |
A-329 | 3-OCH3 | 4-F |
A-330 | - | 4-CN |
A-331 | 2-F | 4-CN |
A-332 | 2-Cl | 4-CN |
A-333 | 2-CH3 | 4-CN |
A-334 | 2-CF3 | 4-CN |
A-335 | 2-OCH3 | 4-CN |
A-336 | 3-F | 4-CN |
A-337 | 3-Cl | 4-CN |
A-338 | 3-CH3 | 4-CN |
A-339 | 3-CF3 | 4-CN |
A-340 | 3-OCH3 | 4-CN |
A-341 | - | 4-NO2 |
A-342 | 2-F | 4-NO2 |
A-343 | 2-Cl | 4-NO2 |
A-344 | 2-CH3 | 4-NO2 |
A-345 | 2-CF3 | 4-NO2 |
序号 | (R6)m | (R7)n |
A-346 | 2-OCH3 | 4-NO2 |
A-347 | 3-F | 4-NO2 |
A-348 | 3-Cl | 4-NO2 |
A-349 | 3-CH3 | 4-NO2 |
A-350 | 3-CF3 | 4-NO2 |
A-351 | 3-OCH3 | 4-NO2 |
A-352 | - | 4-OCH3 |
A-353 | 2-F | 4-OCH3 |
A-354 | 2-Cl | 4-OCH3 |
A-355 | 2-CH3 | 4-OCH3 |
A-356 | 2-CF3 | 4-OCH3 |
A-357 | 2-OCH3 | 4-OCH3 |
A-358 | 3-F | 4-OCH3 |
A-359 | 3-Cl | 4-OCH3 |
A-360 | 3-CH3 | 4-OCH3 |
A-361 | 3-CF3 | 4-OCH3 |
A-362 | 3-OCH3 | 4-OCH3 |
A-363 | - | 4-OCH2CH3 |
A-364 | 2-F | 4-OCH2CH3 |
A-365 | 2-Cl | 4-OCH2CH3 |
A-366 | 2-CH3 | 4-OCH2CH3 |
A-367 | 2-CF3 | 4-OCH2CH3 |
A-368 | 2-OCH3 | 4-OCH2CH3 |
A-369 | 3-F | 4-OCH2CH3 |
A-370 | 3-Cl | 4-OCH2CH3 |
A-371 | 3-CH3 | 4-OCH2CH3 |
A-372 | 3-CF3 | 4-OCH2CH3 |
A-373 | 3-OCH3 | 4-OCH2CH3 |
A-374 | - | 4-OCH(CH3)2 |
A-375 | 2-F | 4-OCH(CH3)2 |
A-376 | 2-Cl | 4-OCH(CH3)2 |
A-377 | 2-CH3 | 4-OCH(CH3)2 |
序号 | (R6)m | (R7)n |
A-378 | 2-CF3 | 4-OCH(CH3)2 |
A-379 | 2-OCH3 | 4-OCH(CH3)2 |
A-380 | 3-F | 4-OCH(CH3)2 |
A-381 | 3-Cl | 4-OCH(CH3)2 |
A-382 | 3-CH3 | 4-OCH(CH3)2 |
A-383 | 3-CF3 | 4-OCH(CH3)2 |
A-384 | 3-OCH3 | 4-OCH(CH3)2 |
A-385 | - | 4-OC(CH3)3 |
A-386 | 2-F | 4-OC(CH3)3 |
A-387 | 2-Cl | 4-OC(CH3)3 |
A-388 | 2-CH3 | 4-OC(CH3)3 |
A-389 | 2-CF3 | 4-OC(CH3)3 |
A-390 | 2-OCH3 | 4-OC(CH3)3 |
A-391 | 3-F | 4-OC(CH3)3 |
A-392 | 3-Cl | 4-OC(CH3)3 |
A-393 | 3-CH3 | 4-OC(CH3)3 |
A-394 | 3-CF3 | 4-OC(CH3)3 |
A-395 | 3-OCH3 | 4-OC(CH3)3 |
A-396 | - | 4-CF3 |
A-397 | 2-F | 4-CF3 |
A-398 | 2-Cl | 4-CF3 |
A-399 | 2-CH3 | 4-CF3 |
A-400 | 2-CF3 | 4-CF3 |
A-401 | 2-OCH3 | 4-CF3 |
A-402 | 3-F | 4-CF3 |
A-403 | 3-Cl | 4-CF3 |
A-404 | 3-CH3 | 4-CF3 |
A-405 | 3-CF3 | 4-CF3 |
A-406 | 3-OCH3 | 4-CF3 |
A-407 | - | 4-SCH3 |
A-408 | 2-F | 4-SCH3 |
A-409 | 2-Cl | 4-SCH3 |
序号 | (R6)m | (R7)n |
A-410 | 2-CH3 | 4-SCH3 |
A-411 | 2-CF3 | 4-SCH3 |
A-412 | 2-OCH3 | 4-SCH3 |
A-413 | 3-F | 4-SCH3 |
A-414 | 3-Cl | 4-SCH3 |
A-415 | 3-CH3 | 4-SCH3 |
A-416 | 3-CF3 | 4-SCH3 |
A-417 | 3-OCH3 | 4-SCH3 |
A-418 | - | 4-C(=O)CH3 |
A-419 | 2-F | 4-C(=O)CH3 |
A-420 | 2-Cl | 4-C(=O)CH3 |
A-421 | 2-CH3 | 4-C(=O)CH3 |
A-422 | 2-CF3 | 4-C(=O)CH3 |
A-423 | 2-OCH3 | 4-C(=O)CH3 |
A-424 | 3-F | 4-C(=O)CH3 |
A-425 | 3-Cl | 4-C(=O)CH3 |
A-426 | 3-CH3 | 4-C(=O)CH3 |
A-427 | 3-CF3 | 4-C(=O)CH3 |
A-428 | 3-OCH3 | 4-C(=O)CH3 |
A-429 | - | 4-C(=NOCH3)CH3 |
A-430 | 2-F | 4-C(=NOCH3)CH3 |
A-431 | 2-Cl | 4-C(=NOCH3)CH3 |
A-432 | 2-CH3 | 4-C(=NOCH3)CH3 |
A-433 | 2-CF3 | 4-C(=NOCH3)CH3 |
A-434 | 2-OCH3 | 4-C(=NOCH3)CH3 |
A-435 | 3-F | 4-C(=NOCH3)CH3 |
A-436 | 3-Cl | 4-C(=NOCH3)CH3 |
A-437 | 3-CH3 | 4-C(=NOCH3)CH3 |
A-438 | 3-CF3 | 4-C(=NOCH3)CH3 |
A-439 | 3-OCH3 | 4-C(=NOCH3)CH3 |
A-440 | - | 4-C6H5 |
A-441 | 2-F | 4-C6H5 |
序号 | (R6)m | (R7)n |
A-442 | 2-Cl | 4-C6H5 |
A-443 | 2-CH3 | 4-C6H5 |
A-444 | 2-CF3 | 4-C6H5 |
A-445 | 2-OCH3 | 4-C6H5 |
A-446 | 3-F | 4-C6H5 |
A-447 | 3-Cl | 4-C6H5 |
A-448 | 3-CH3 | 4-C6H5 |
A-449 | 3-CF3 | 4-C6H5 |
A-450 | 3-OCH3 | 4-C6H5 |
A-451 | - | 2,4-(CH3)2 |
A-452 | 2-F | 2,4-(CH3)2 |
A-453 | 2-Cl | 2,4-(CH3)2 |
A-454 | 2-CH3 | 2,4-(CH3)2 |
A-455 | 2-CF3 | 2,4-(CH3)2 |
A-456 | 2-OCH3 | 2,4-(CH3)2 |
A-457 | 3-F | 2,4-(CH3)2 |
A-458 | 3-Cl | 2,4-(CH3)2 |
A-459 | 3-CH3 | 2,4-(CH3)2 |
A-460 | 3-CF3 | 2,4-(CH3)2 |
A-461 | 3-OCH3 | 2,4-(CH3)2 |
A-462 | - | 2,4-(CH2CH3)2 |
A-463 | 2-F | 2,4-(CH2CH3)2 |
A-464 | 2-Cl | 2,4-(CH2CH3)2 |
A-465 | 2-CH3 | 2,4-(CH2CH3)2 |
A-466 | 2-CF3 | 2,4-(CH2CH3)2 |
A-467 | 2-OCH3 | 2,4-(CH2CH3)2 |
A-468 | 3-F | 2,4-(CH2CH3)2 |
A-469 | 3-Cl | 2,4-(CH2CH3)2 |
A-470 | 3-CH3 | 2,4-(CH2CH3)2 |
A-471 | 3-CF3 | 2,4-(CH2CH3)2 |
A-472 | 3-OCH3 | 2,4-(CH2CH3)2 |
A-473 | - | 2,4-Br2 |
序号 | (R6)m | (R7)n |
A-474 | 2-F | 2,4-Br2 |
A-475 | 2-Cl | 2,4-Br2 |
A-476 | 2-CH3 | 2,4-Br2 |
A-477 | 2-CF3 | 2,4-Br2 |
A-478 | 2-OCH3 | 2,4-Br2 |
A-479 | 3-F | 2,4-Br2 |
A-480 | 3-Cl | 2,4-Br2 |
A-481 | 3-CH3 | 2,4-Br2 |
A-482 | 3-CF3 | 2,4-Br2 |
A-483 | 3-OCH3 | 2,4-Br2 |
A-484 | - | 2,4-Cl2 |
A-485 | 2-F | 2,4-Cl2 |
A-486 | 2-Cl | 2,4-Cl2 |
A-487 | 2-CH3 | 2,4-Cl2 |
A-488 | 2-CF3 | 2,4-Cl2 |
A-489 | 2-OCH3 | 2,4-Cl2 |
A-490 | 3-F | 2,4-Cl2 |
A-491 | 3-Cl | 2,4-Cl2 |
A-492 | 3-CH3 | 2,4-Cl2 |
A-493 | 3-CF3 | 2,4-Cl2 |
A-494 | 3-OCH3 | 2,4-Cl2 |
A-495 | - | 2,4-F2 |
A-496 | 2-F | 2,4-F2 |
A-497 | 2-Cl | 2,4-F2 |
A-498 | 2-CH3 | 2,4-F2 |
A-499 | 2-CF3 | 2,4-F2 |
A-500 | 2-OCH3 | 2,4-F2 |
A-501 | 3-F | 2,4-F2 |
A-502 | 3-Cl | 2,4-F2 |
A-503 | 3-CH3 | 2,4-F2 |
A-504 | 3-CF3 | 2,4-F2 |
A-505 | 3-OCH3 | 2,4-F2 |
序号 | (R6)m | (R7)n |
A-506 | 2-F | 2,4-(OCH3)2 |
A-507 | 2-Cl | 2,4-(OCH3)2 |
A-508 | 2-CH3 | 2,4-(OCH3)2 |
A-509 | 2-CF3 | 2,4-(OCH3)2 |
A-510 | 2-OCH3 | 2,4-(OCH3)2 |
A-511 | 3-F | 2,4-(OCH3)2 |
A-512 | 3-Cl | 2,4-(OCH3)2 |
A-513 | 3-CH3 | 2,4-(OCH3)2 |
A-514 | 3-CF3 | 2,4-(OCH3)2 |
A-515 | 3-OCH3 | 2,4-(OCH3)2 |
A-516 | - | 2,4-(CF3)2 |
A-517 | 2-F | 2,4-(CF3)2 |
A-518 | 2-Cl | 2,4-(CF3)2 |
A-519 | 2-CH3 | 2,4-(CF3)2 |
A-520 | 2-CF3 | 2,4-(CF3)2 |
A-521 | 2-OCH3 | 2,4-(CF3)2 |
A-522 | 3-F | 2,4-(CF3)2 |
A-523 | 3-Cl | 2,4-(CF3)2 |
A-524 | 3-CH3 | 2,4-(CF3)2 |
A-525 | 3-CF3 | 2,4-(CF3)2 |
A-526 | 3-OCH3 | 2,4-(CF3)2 |
A-527 | - | 2,5-(CH3)2 |
A-528 | 2-F | 2,5-(CH3)2 |
A-529 | 2-Cl | 2,5-(CH3)2 |
A-530 | 2-CH3 | 2,5-(CH3)2 |
A-531 | 2-CF3 | 2,5-(CH3)2 |
A-532 | 2-OCH3 | 2,5-(CH3)2 |
A-533 | 3-F | 2,5-(CH3)2 |
A-534 | 3-Cl | 2,5-(CH3)2 |
A-535 | 3-CH3 | 2,5-(CH3)2 |
A-536 | 3-CF3 | 2,5-(CH3)2 |
A-537 | 3-OCH3 | 2,5-(CH3)2 |
序号 | (R6)m | (R7)n |
A-538 | - | 2,5-Cl2 |
A-539 | 2-F | 2,5-Cl2 |
A-540 | 2-Cl | 2,5-Cl2 |
A-541 | 2-CH3 | 2,5-Cl2 |
A-542 | 2-CF3 | 2,5-Cl2 |
A-543 | 2-OCH3 | 2,5-Cl2 |
A-544 | 3-F | 2,5-Cl2 |
A-545 | 3-Cl | 2,5-Cl2 |
A-546 | 3-CH3 | 2,5-Cl2 |
A-547 | 3-CF3 | 2,5-Cl2 |
A-548 | 3-OCH3 | 2,5-Cl2 |
A-549 | - | 2,5-F2 |
A-550 | 2-F | 2,5-F2 |
A-551 | 2-Cl | 2,5-F2 |
A-552 | 2-CH3 | 2,5-F2 |
A-553 | 2-CF3 | 2,5-F2 |
A-554 | 2-OCH3 | 2,5-F2 |
A-555 | 3-F | 2,5-F2 |
A-556 | 3-Cl | 2,5-F2 |
A-557 | 3-CH3 | 2,5-F2 |
A-558 | 3-CF3 | 2,5-F2 |
A-559 | 3-OCH3 | 2,5-F2 |
A-560 | - | 2,5-(OCH3)2 |
A-561 | 2-F | 2,5-(OCH3)2 |
A-562 | 2-Cl | 2,5-(OCH3)2 |
A-563 | 2-CH3 | 2,5-(OCH3)2 |
A-564 | 2-CF3 | 2,5-(OCH3)2 |
A-565 | 2-OCH3 | 2,5-(OCH3)2 |
A-566 | 3-F | 2,5-(OCH3)2 |
A-567 | 3-Cl | 2,5-(OCH3)2 |
A-568 | 3-CH3 | 2,5-(OCH3)2 |
A-569 | 3-CF3 | 2,5-(OCH3)2 |
序号 | (R6)m | (R7)n |
A-570 | 3-OCH3 | 2,5-(OCH3)2 |
A-571 | - | 2,5-(CF3)2 |
A-572 | 2-F | 2,5-(CF3)2 |
A-573 | 2-Cl | 2,5-(CF3)2 |
A-574 | 2-CH3 | 2,5-(CF3)2 |
A-575 | 2-CF3 | 2,5-(CF3)2 |
A-576 | 2-OCH3 | 2,5-(CF3)2 |
A-577 | 3-F | 2,5-(CF3)2 |
A-578 | 3-Cl | 2,5-(CF3)2 |
A-579 | 3-CH3 | 2,5-(CF3)2 |
A-580 | 3-CF3 | 2,5-(CF3)2 |
A-581 | 3-OCH3 | 2,5-(CF3)2 |
A-582 | - | 2,5-(SCH3)2 |
A-583 | 2-F | 2,5-(SCH3)2 |
A-584 | 2-Cl | 2,5-(SCH3)2 |
A-585 | 2-CH3 | 2,5-(SCH3)2 |
A-586 | 2-CF3 | 2,5-(SCH3)2 |
A-587 | 2-OCH3 | 2,5-(SCH3)2 |
A-588 | 3-F | 2,5-(SCH3)2 |
A-589 | 3-Cl | 2,5-(SCH3)2 |
A-590 | 3-CH3 | 2,5-(SCH3)2 |
A-591 | 3-CF3 | 2,5-(SCH3)2 |
A-592 | 3-OCH3 | 2,5-(SCH3)2 |
A-593 | - | 2,6-(CH3)2 |
A-594 | 2-F | 2,6-(CH3)2 |
A-595 | 2-Cl | 2,6-(CH3)2 |
A-596 | 2-CH3 | 2,6-(CH3)2 |
A-597 | 2-CF3 | 2,6-(CH3)2 |
A-598 | 2-OCH3 | 2,6-(CH3)2 |
A-599 | 3-F | 2,6-(CH3)2 |
A-600 | 3-Cl | 2,6-(CH3)2 |
A-601 | 3-CH3 | 2,6-(CH3)2 |
序号 | (R6)m | (R7)n |
A-602 | 3-CF3 | 2,6-(CH3)2 |
A-603 | 3-OCH3 | 2,6-(CH3)2 |
A-604 | - | 3,5-(CH3)2 |
A-605 | 2-F | 3,5-(CH3)2 |
A-606 | 2-Cl | 3,5-(CH3)2 |
A-607 | 2-CH3 | 3,5-(CH3)2 |
A-608 | 2-CF3 | 3,5-(CH3)2 |
A-609 | 2-OCH3 | 3,5-(CH3)2 |
A-610 | 3-F | 3,5-(CH3)2 |
A-611 | 3-Cl | 3,5-(CH3)2 |
A-612 | 3-CH3 | 3,5-(CH3)2 |
A-613 | 3-CF3 | 3,5-(CH3)2 |
A-614 | 3-OCH3 | 3,5-(CH3)2 |
A-615 | - | 3,5-(CF3)2 |
A-616 | 2-F | 3,5-(CF3)2 |
A-617 | 2-Cl | 3,5-(CF3)2 |
A-618 | 2-CH3 | 3,5-(CF3)2 |
A-619 | 2-CF3 | 3,5-(CF3)2 |
A-620 | 2-OCH3 | 3,5-(CF3)2 |
A-621 | 3-F | 3,5-(CF3)2 |
A-622 | 3-Cl | 3,5-(CF3)2 |
A-623 | 3-CH3 | 3,5-(CF3)2 |
A-624 | 3-CF3 | 3,5-(CF3)2 |
A-625 | 3-OCH3 | 3,5-(CF3)2 |
A-626 | - | 3-Cl,4-F |
A-627 | 2-F | 3-Cl,4-F |
A-628 | 2-Cl | 3-Cl,4-F |
A-629 | 2-CH3 | 3-Cl,4-F |
A-630 | 2-CF3 | 3-Cl,4-F |
A-631 | 2-OCH3 | 3-Cl,4-F |
A-632 | 3-F | 3-Cl,4-F |
A-633 | 3-Cl | 3-Cl,4-F |
序号 | (R6)m | (R7)n |
A-634 | 3-CH3 | 3-Cl,4-F |
A-635 | 3-CF3 | 3-Cl,4-F |
A-636 | 3-OCH3 | 3-Cl,4-F |
A-637 | - | 3-CH3,4-F |
A-638 | 2-F | 3-CH3,4-F |
A-639 | 2-Cl | 3-CH3,4-F |
A-640 | 2-CH3 | 3-CH3,4-F |
A-641 | 2-CF3 | 3-CH3,4-F |
A-642 | 2-OCH3 | 3-CH3,4-F |
A-643 | 3-F | 3-CH3,4-F |
A-644 | 3-Cl | 3-CH3,4-F |
A-645 | 3-CH3 | 3-CH3,4-F |
A-646 | 3-CF3 | 3-CH3,4-F |
A-647 | 3-OCH3 | 3-CH3,4-F |
A-648 | - | 2-Cl,4-F |
A-649 | 2-F | 2-Cl,4-F |
A-650 | 2-Cl | 2-Cl,4-F |
A-651 | 2-CH3 | 2-Cl,4-F |
A-652 | 2-CF3 | 2-Cl,4-F |
A-653 | 2-OCH3 | 2-Cl,4-F |
A-654 | 3-F | 2-Cl,4-F |
A-655 | 3-Cl | 2-Cl,4-F |
A-656 | 3-CH3 | 2-Cl,4-F |
A-657 | 3-CF3 | 2-Cl,4-F |
A-658 | 3-OCH3 | 2-Cl,4-F |
A-659 | - | 2-Cl,4-OCH3 |
A-660 | 2-F | 2-Cl,4-OCH3 |
A-661 | 2-Cl | 2-Cl,4-OCH3 |
A-662 | 2-CH3 | 2-Cl,4-OCH3 |
A-663 | 2-CF3 | 2-Cl,4-OCH3 |
A-664 | 2-OCH3 | 2-Cl,4-OCH3 |
A-665 | 3-F | 2-Cl,4-OCH3 |
序号 | (R6)m | (R7)n |
A-666 | 3-Cl | 2-Cl,4-OCH3 |
A-667 | 3-CH3 | 2-Cl,4-OCH3 |
A-668 | 3-CF3 | 2-Cl,4-OCH3 |
A-669 | 3-OCH3 | 2-Cl,4-OCH3 |
A-670 | - | 2-F,4-Cl |
A-671 | 2-F | 2-F,4-Cl |
A-672 | 2-Cl | 2-F,4-Cl |
A-673 | 2-CH3 | 2-F,4-Cl |
A-674 | 2-CF3 | 2-F,4-Cl |
A-675 | 2-OCH3 | 2-F,4-Cl |
A-676 | 3-F | 2-F,4-Cl |
A-677 | 3-Cl | 2-F,4-Cl |
A-678 | 3-CH3 | 2-F,4-Cl |
A-679 | 3-CF3 | 2-F,4-Cl |
A-680 | 3-OCH3 | 2-F,4-Cl |
A-681 | - | 2-F,4-Br |
A-682 | 2-F | 2-F,4-Br |
A-683 | 2-Cl | 2-F,4-Br |
A-684 | 2-CH3 | 2-F,4-Br |
A-685 | 2-CF3 | 2-F,4-Br |
A-686 | 2-OCH3 | 2-F,4-Br |
A-687 | 3-F | 2-F,4-Br |
A-688 | 3-Cl | 2-F,4-Br |
A-689 | 3-CH3 | 2-F,4-Br |
A-690 | 3-CF3 | 2-F,4-Br |
A-691 | 3-OCH3 | 2-F,4-Br |
A-692 | - | 2-F,4-CH3 |
A-693 | 2-F | 2-F,4-CH3 |
A-694 | 2-Cl | 2-F,4-CH3 |
A-695 | 2-CH3 | 2-F,4-CH3 |
A-696 | 2-CF3 | 2-F,4-CH3 |
A-697 | 2-OCH3 | 2-F,4-CH3 |
序号 | (R6)m | (R7)n |
A-698 | 3-F | 2-F,4-CH3 |
A-699 | 3-Cl | 2-F,4-CH3 |
A-700 | 3-CH3 | 2-F,4-CH3 |
A-701 | 3-CF3 | 2-F,4-CH3 |
A-702 | 3-OCH3 | 2-F,4-CH3 |
A-703 | - | 2-F,4-CF3 |
A-704 | 2-F | 2-F,4-CF3 |
A-705 | 2-Cl | 2-F,4-CF3 |
A-706 | 2-CH3 | 2-F,4-CF3 |
A-707 | 2-CF3 | 2-F,4-CF3 |
A-708 | 2-OCH3 | 2-F,4-CF3 |
A-709 | 3-F | 2-F,4-CF3 |
A-710 | 3-Cl | 2-F,4-CF3 |
A-711 | 3-CH3 | 2-F,4-CF3 |
A-712 | 3-CF3 | 2-F,4-CF3 |
A-713 | 3-OCH3 | 2-F,4-CF3 |
A-714 | - | 2-F,4-OCH3 |
A-715 | 2-F | 2-F,4-OCH3 |
A-716 | 2-Cl | 2-F,4-OCH3 |
A-717 | 2-CH3 | 2-F,4-OCH3 |
A-718 | 2-CF3 | 2-F,4-OCH3 |
A-719 | 2-OCH3 | 2-F,4-OCH3 |
A-720 | 3-F | 2-F,4-OCH3 |
A-721 | 3-Cl | 2-F,4-OCH3 |
A-722 | 3-CH3 | 2-F,4-OCH3 |
A-723 | 3-CF3 | 2-F,4-OCH3 |
A-724 | 3-OCH3 | 2-F,4-OCH3 |
A-725 | - | 2-CH3,4-OCH3 |
A-726 | 2-F | 2-CH3,4-OCH3 |
A-727 | 2-Cl | 2-CH3,4-OCH3 |
A-728 | 2-CH3 | 2-CH3,4-OCH3 |
A-729 | 2-CF3 | 2-CH3,4-OCH3 |
序号 | (R6)m | (R7)n |
A-730 | 2-OCH3 | 2-CH3,4-OCH3 |
A-731 | 3-F | 2-CH3,4-OCH3 |
A-732 | 3-Cl | 2-CH3,4-OCH3 |
A-733 | 3-CH3 | 2-CH3,4-OCH3 |
A-734 | 3-CF3 | 2-CH3,4-OCH3 |
A-735 | 3-OCH3 | 2-CH3,4-OCH3 |
A-736 | - | 2-CH3,4-Cl |
A-737 | 2-F | 2-CH3,4-Cl |
A-738 | 2-Cl | 2-CH3,4-Cl |
A-739 | 2-CH3 | 2-CH3,4-Cl |
A-740 | 2-CF3 | 2-CH3,4-Cl |
A-741 | 2-OCH3 | 2-CH3,4-Cl |
A-742 | 3-F | 2-CH3,4-Cl |
A-743 | 3-Cl | 2-CH3,4-Cl |
A-744 | 3-CH3 | 2-CH3,4-Cl |
A-745 | 3-CF3 | 2-CH3,4-Cl |
A-746 | 3-OCH3 | 2-CH3,4-Cl |
A-747 | - | 2-CH3,4-F |
A-748 | 2-F | 2-CH3,4-F |
A-749 | 2-Cl | 2-CH3,4-F |
A-750 | 2-CH3 | 2-CH3,4-F |
A-751 | 2-CF3 | 2-CH3,4-F |
A-752 | 2-OCH3 | 2-CH3,4-F |
A-753 | 3-F | 2-CH3,4-F |
A-754 | 3-Cl | 2-CH3,4-F |
A-755 | 3-CH3 | 2-CH3,4-F |
A-756 | 3-CF3 | 2-CH3,4-F |
A-757 | 3-OCH3 | 2-CH3,4-F |
A-758 | - | 2-CH3,4-CF3 |
A-759 | 2-F | 2-CH3,4-CF3 |
A-760 | 2-Cl | 2-CH3,4-CF3 |
A-761 | 2-CH3 | 2-CH3,4-CF3 |
序号 | (R6)m | (R7)n |
A-762 | 2-CF3 | 2-CH3,4-CF3 |
A-763 | 2-OCH3 | 2-CH3,4-CF3 |
A-764 | 3-F | 2-CH3,4-CF3 |
A-765 | 3-Cl | 2-CH3,4-CF3 |
A-766 | 3-CH3 | 2-CH3,4-CF3 |
A-767 | 3-CF3 | 2-CH3,4-CF3 |
A-768 | 3-OCH3 | 2-CH3,4-CF3 |
A-769 | - | 2-OCH3,4-F |
A-770 | 2-F | 2-OCH3,4-F |
A-771 | 2-Cl | 2-OCH3,4-F |
A-772 | 2-CH3 | 2-OCH3,4-F |
A-773 | 2-CF3 | 2-OCH3,4-F |
A-774 | 2-OCH3 | 2-OCH3,4-F |
A-775 | 3-F | 2-OCH3,4-F |
A-776 | 3-Cl | 2-OCH3,4-F |
A-777 | 3-CH3 | 2-OCH3,4-F |
A-778 | 3-CF3 | 2-OCH3,4-F |
A-779 | 3-OCH3 | 2-OCH3,4-F |
A-780 | - | 2-OCH3,4-Cl |
A-781 | 2-F | 2-OCH3,4-Cl |
A-782 | 2-Cl | 2-OCH3,4-Cl |
A-783 | 2-CH3 | 2-OCH3,4-Cl |
A-784 | 2-CF3 | 2-OCH3,4-Cl |
A-785 | 2-OCH3 | 2-OCH3,4-Cl |
A-786 | 3-F | 2-OCH3,4-Cl |
A-787 | 3-Cl | 2-OCH3,4-Cl |
A-788 | 3-CH3 | 2-OCH3,4-Cl |
A-789 | 3-CF3 | 2-OCH3,4-Cl |
A-790 | 3-OCH3 | 2-OCH3,4-Cl |
A-791 | - | 3-NO2,4-CH3 |
A-792 | 2-F | 3-NO2,4-CH3 |
A-793 | 2-Cl | 3-NO2,4-CH3 |
(R6)m | (R7)n | |
A-794 | 2-CH3 | 3-NO2,4-CH3 |
A-795 | 2-CF3 | 3-NO2,4-CH3 |
A-796 | 2-OCH3 | 3-NO2,4-CH3 |
A-797 | 3-F | 3-NO2,4-CH3 |
A-798 | 3-Cl | 3-NO2,4-CH3 |
A-799 | 3-CH3 | 3-NO2,4-CH3 |
A-800 | 3-CF3 | 3-NO2,4-CH3 |
A-801 | 3-OCH3 | 3-NO2,4-CH3 |
A-802 | - | 2-CF3,4-Cl |
A-803 | 3-F | 2-CF3,4-Cl |
A-804 | 3-Cl | 2-CF3,4-Cl |
A-805 | 3-CH3 | 2-CF3,4-Cl |
A-806 | 3-CF3 | 2-CF3,4-Cl |
A-807 | 3-OCF3 | 2-CF3,4-Cl |
A-808 | - | 2-Cl,4-CF3 |
A-809 | 3-F | 2-Cl,4-CF3 |
A-810 | 3-Cl | 2-Cl,4-CF3 |
A-811 | 3-CH3 | 2-Cl,4-CF3 |
A-812 | 3-CF3 | 2-Cl,4-CF3 |
A-813 | 3-OCF3 | 2-Cl,4-CF3 |
A-814 | - | 2-CF3,4-OCH3 |
A-815 | 3-F | 2-CF3,4-OCH3 |
A-816 | 3-Cl | 2-CF3,4-OCH3 |
A-817 | 3-CH3 | 2-CF3,4-OCH3 |
A-818 | 3-CF3 | 2-CF3,4-OCH3 |
A-819 | 3-OCF3 | 2-CF3,4-OCH3 |
A-820 | - | 3-Cl,4-CF3 |
A-821 | 3-F | 3-Cl,4-CF3 |
A-822 | 3-Cl | 3-Cl,4-CF3 |
A-823 | 3-CH3 | 3-Cl,4-CF3 |
A-824 | 3-CF3 | 3-Cl,4-CF3 |
A-825 | 3-OCF3 | 3-Cl,4-CF3 |
序号 | (R6)m | (R7)n |
A-826 | - | 2-CF3,5-F |
A-827 | 3-F | 2-CF3,5-F |
A-828 | 3-Cl | 2-CF3,5-F |
A-829 | 3-CH3 | 2-CF3,5-F |
A-830 | 3-CF3 | 2-CF3,5-F |
A-831 | 3-OCF3 | 2-CF3,5-F |
A-832 | - | 2-CF3,5-Cl |
A-833 | 3-F | 2-CF3,5-Cl |
A-834 | 3-Cl | 2-CF3,5-Cl |
A-835 | 3-CH3 | 2-CF3,5-Cl |
A-836 | 3-CF3 | 2-CF3,5-Cl |
A-837 | 3-OCF3 | 2-CF3,5-Cl |
A-838 | - | 2-Cl,5-CF3 |
A-839 | 3-F | 2-Cl,5-CF3 |
A-840 | 3-Cl | 2-Cl,5-CF3 |
A-841 | 3-CH3 | 2-Cl,5-CF3 |
A-842 | 3-CF3 | 2-Cl,5-CF3 |
A-843 | 3-OCF3 | 2-Cl,5-CF3 |
A-844 | - | 2-F,5-CF3 |
A-845 | 3-F | 2-F,5-CF3 |
A-846 | 3-Cl | 2-F,5-CF3 |
A-847 | 3-CH3 | 2-F,5-CF3 |
A-848 | 3-CF3 | 2-F,5-CF3 |
A-849 | 3-OCF3 | 2-F,5-CF3 |
A-850 | - | 3-F,4-CF3 |
A-851 | 3-F | 3-F,4-CF3 |
A-852 | 3-Cl | 3-F,4-CF3 |
A-853 | 3-CH3 | 3-F,4-CF3 |
A-854 | 3-CF3 | 3-F,4-CF3 |
A-855 | 3-OCF3 | 3-F,4-CF3 |
A-856 | - | 3-Cl,4-CF3 |
A-857 | 3-F | 3-Cl,4-CF3 |
序号 | (R6)m | (R7)n |
A-858 | 3-Cl | 3-Cl,4-CF3 |
A-859 | 3-CH3 | 3-Cl,4-CF3 |
A-860 | 3-CF3 | 3-Cl,4-CF3 |
A-861 | 3-OCF3 | 3-Cl,4-CF3 |
A-862 | - | 3-Cl,4-Cl |
A-863 | 3-F | 3-Cl,4-Cl |
A-864 | 3-Cl | 3-Cl,4-Cl |
A-865 | 3-CH3 | 3-Cl,4-Cl |
A-866 | 3-CF3 | 3-Cl,4-Cl |
A-867 | 3-OCF3 | 3-Cl,4-Cl |
A-868 | - | 3-F,4-Cl |
A-869 | 3-F | 3-F,4-Cl |
A-870 | 3-Cl | 3-F,4-Cl |
A-871 | 3-CH3 | 3-F,4-Cl |
A-872 | 3-CF3 | 3-F,4-Cl |
A-873 | 3-OCF3 | 3-F,4-Cl |
A-874 | - | 3-CF3,4-Cl |
A-875 | 3-F | 3-CF3,4-Cl |
A-876 | 3-Cl | 3-CF3,4-Cl |
A-877 | 3-CH3 | 3-CF3,4-Cl |
A-878 | 3-CF3 | 3-CF3,4-Cl |
A-879 | 3-OCF3 | 3-CF3,4-Cl |
A-880 | - | - |
本发明化合物可以通过不同途径得到。有利的是它们可由式II的吡啶衍生物通过在碱性条件下与式III的磺酸或活化的磺酸衍生物反应而得到:
在式III中,L为合适的离去基团,如羟基或卤素,优选氯。
该反应通常在-30℃至120℃,优选-10℃至100℃的温度下在惰性有机溶剂中在碱存在下进行[参见Lieb.Ann.Chem.641(1990)]。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,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,特别优选二异丙基醚、乙醚和四氢呋喃。还可以使用所述溶剂的混合物。
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、三异丙基乙基胺和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,以及双环胺类。特别优选吡啶、三乙胺和碳酸钾。碱通常以催化量使用;然而,它们还可以等摩尔量或过量使用或者合适的话用作溶剂。
原料通常以等摩尔量相互反应。就收率而言,可能有利的是基于III使用过量II。
制备化合物I所需的原料可以市购或由文献已知[WO 99/42443;EP-A483667;WO 96/10022;WO 00/73295;J.für praktische Chemie,第695页(1994);Heterocycles,第675页(1995);Tetrahedron,第12、483页(1996);Chem.Pharm.Bull.,第1927页(1973);J.Chem.Soc.,第426页(1942);EP-A 983982;Synthesis,第852页(1986)],或者它们可以按照所引用的文献制备。
吡啶衍生物II例如可以通过还原相应的腈、肟或羧酰胺而制备。该合成和前体例如可以参见J.Org.Chem.23,714(1958),J.Prakt.Chem.336(8),695(1994),Chem.Pharm.Bull.1927,21(1973),US 4,439,609,Houben-Weyl,Methoden der Organischen Chemie,Georg Thieme VerlagStuttgart,第10/4卷(1968)、第11/2卷(1957)和第E5卷(1985),HeterocyclicCompounds,第14卷,第1-4部分,Wiley New York 1974-1975,Methodsin Science of Synthesis,第15卷,Tetrahedron 57,4489(2001),DokladyAkadem Nauk SSSR 164,816(1965),Eur.J.Org.Chem.1371(2001),Tetrahedron 57,4059(2001),US 2005/0239791,Heterocycles 65,8(2005),European Journal of Organic Chemistry 8,1559-1568(2003)。
或者,式I化合物还可以通过使式II的吡啶衍生物与式IV的4-卤代苯基磺酰卤反应,然后构建联苯基单元而制备。后者可以在Stille或优选Suzuki偶联条件下进行。
在式IV中,Hal和L为卤素,L优选为氯且“Hal”尤其为溴或碘。
向式V的吡啶基磺酰胺的转化在与化合物II和III缩合相同的条件下进行。
吡啶基磺酰胺V与硼酸衍生物VI或其酯的Suzuki偶联通常在20-180℃,优选40-120℃的温度下在惰性有机溶剂中在碱和铂金属,尤其是钯催化剂存在下进行[参见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);WO 2002/42275]。
合适的催化剂尤其是四(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;三叔丁基膦/钯-二亚苄基丙酮。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,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、二烷、茴香醚、四氢呋喃和二甲氧基乙烷,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、二烷和二甲氧基乙烷。还可以使用所述溶剂的混合物。
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、三异丙基乙基胺和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,以及双环胺类。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。
碱通常以等摩尔量使用;然而,它们还可以过量使用或者合适的话用作溶剂。
原料通常以等摩尔量相互反应。就收率而言,可能有利的是基于V使用过量的VI。
中间体IV可以如下列反应方案所示通过用烷基卤化镁如(CH3)2CHMgCl、SO2和SO2Cl2处理而由相应的苯基卤VII制备:
硼酸衍生物VI或其酯可以如Synlett 8,1204(2003),J.Org.Chem.68,3729(2003),Synthesis,442(2000),J.Org.Chem.60,7508(1995)或WO2002/42275所述得到。
以常规方式后处理反应混合物,例如通过与水混合、分离各相并且合适的话色谱法提纯粗产物。某些中间体和终产物以无色或浅棕色粘性油形式得到,它们在减压和温和升高的温度下提纯或除去挥发性组分。若中间体和终产物以固体得到,则还可以通过重结晶或浸煮进行提纯。
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处理联苯磺酰胺I[Journal of Medicinal Chemistry,38(11),1892-1903(1995);WO 03/64572]或用无机氧化剂如过氧化氢处理联苯磺酰胺I[参见Jounal of Heterocyclic Chemistry,18(7),1305-8(1981)]或用过硫酸氢钾制剂处理联苯磺酰胺I[参见Journal of the AmericanChemical Society,123(25),5962-5973(2001)]。氧化可得到纯的单-N-氧化物或在分子中存在第二个吡啶环时得到不同N-氧化物的混合物。不同的N-氧化物可以通过常规方法如色谱法分离。
若各化合物I不能通过上述途径获得,则可以通过衍生其它化合物I而制备它们。
若合成得到异构体的混合物,则分离通常不是必须的,因为在某些情况下各异构体可能在为了应用的后处理过程中或在施用过程中(例如在光、酸或碱的作用下)相互转化。这类转化也可以在使用后发生,例如在处理植物时,在处理的植物中或在待防治的有害真菌中。
化合物I适于作为杀真菌剂。它们对宽范围的植物病原性真菌具有显著效力,所述真菌尤其选自子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)、半知菌纲(Deuteromycetes)和Peronosporomycetes(同义词:卵菌纲(Oomycetes))真菌。它们中的一些内吸有效并可以作为叶面杀真菌剂、拌种用杀真菌剂和土壤杀真菌剂用于作物保护中。
它们对在各种栽培植物如小麦、黑麦、大麦、燕麦、稻、玉米、草坪、香蕉、棉花、大豆、咖啡、甘蔗、葡萄藤、水果和观赏植物以及蔬菜如黄瓜、豆类、西红柿、土豆和葫芦科植物以及这些植物的种子中防治大量真菌尤其重要。
它们尤其适于防治下列植物病害:
●蔬菜、油菜、制糖甜菜、水果和稻上的链格孢(Alternaria)属(例如土豆和西红柿上的早疫链格孢(A.solani)或链格孢(A.alternata)),
●制糖甜菜和蔬菜上的丝囊霉(Aphanomyces)属,
●禾谷类和蔬菜上的壳二孢(Ascochyta)属;
●玉米、禾谷类、稻和草坪中的平脐蠕孢(Bipolaris)属和内脐蠕孢(Drechslera)属(例如玉米上的玉米内脐蠕孢(D.maydis));
●禾谷类中的禾白粉菌(Blumeria graminis)(白粉病),
●草莓、蔬菜、观赏植物和葡萄藤上的灰葡萄孢(Botrytis cinerea)(灰霉病),
●莴苣上的莴苣盘梗霉(Bremia lactucae),
●玉米、大豆、稻和制糖甜菜上的尾孢(Cercospora)属,
●玉米、禾谷类、稻上的旋孢腔菌(Cochliobolus)属(例如禾谷类上的禾旋孢腔菌(Cochliobolus sativus),稻上的宫部旋孢腔菌(Cochliobolusmiyabeanus)),
●大豆和棉花上的剌盘孢(Colletotricum)属,
●玉米、禾谷类、稻和草坪上的内脐蠕孢(Drechslera)属、核腔菌(Pyrenophora)属(例如大麦上的大麦网斑内脐蠕孢(D.teres)或小麦上的D.tritci-repentis);
●由Phaeoacremonium chlamydosporium、Ph.Aleophilum和层卧孔菌(Formitipora punctata)(同义词斑孔木层孔菌(Phellinus punctatus))引起的葡萄藤上的Esca;
●玉米上的突脐蠕孢(Exserohilum)属;
●葫芦科植物上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea);
●各种植物上的镰孢霉(Fusarium)属和轮枝孢(Verticillium)属(例如禾谷类上的禾本科镰孢(F.graminearum)或大刀镰孢(F.culmorum)或多种植物如西红柿上的尖镰孢(F.oxysporum));
●禾谷类上的禾顶囊壳(Gaeumanomyces graminis)属;
●禾谷类和稻上的赤霉(Gibberella)属(例如稻上的藤仓赤霉(Gibberellafujikuroi));
●稻上的Grainstaining complex;
●玉米和稻上的长蠕孢(Helminthosporium)属;
●禾谷类上的Michrodochium nivale;
●禾谷类、香蕉和花生上的球腔菌(Mycosphaerella)属(例如小麦上的禾生球腔菌(M.graminicola)或香蕉上的M.fijiesis);
●卷心菜和葱类植物上的霜霉(Peronospora)属(例如卷心菜上的芸苔霜霉(P.brassicae)或洋葱上的葱霜霉(P.destructor));
●大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(Phakopsara meibomiae);
●大豆和向日葵上的拟茎点霉(Phomopsis)属;
●土豆和西红柿上的致病疫霉(Phytophthora infestans);
●各种植物上的疫霉(Phytophthora)属(例如红辣椒上的辣椒疫霉(P.capsici));
●葡萄藤上的葡萄生单轴霉(Plasmopara viticola),
●苹果上的苹果白粉病菌(Podosphaera leucotricha),
●禾谷类上的小麦基腐病菌(Pseudocercosporella herpotrichoides),
●各种植物上的假霜霉(Pseudoperonospora)属(例如黄瓜上的古巴霜霉(P.cubenis)或啤酒花上的葎草假霜霉(P.humili));
●各种植物上的柄锈菌(Puccinia)属(例如禾谷类上的小麦柄锈菌(P.triticina)、条形柄锈病(P.striformis)、大麦柄锈病(P.hordei)或禾柄锈菌(P.graminis),天门冬属上的天门冬属柄锈病(P.asparagi));
●稻上的稻瘟病菌(Pyricularia oryzae)、木伏革菌(Corticium sasakii)、帚梗柱孢属(Sarocladium oryzae)、稻叶鞘腐败病(S.attenuatum)、稻叶黑粉菌(Entyloma oryzae),
●草坪和禾谷类上的稻梨孢菌(Pyricularia grisea),
●草坪、稻、玉米、棉花、油菜、向日葵、制糖甜菜、蔬菜和其他植物上的腐霉(Pythium)属(例如各种植物上的终极腐霉(P.ultiumum),草坪上的瓜果腐霉(P.aphanidermatum));
●棉花、稻、土豆、草坪、玉米、油菜、制糖甜菜、蔬菜和各种植物上的丝核菌(Rhizoctonia)属(例如甜菜和各种植物上的立枯丝核病菌(R.solani));
●大麦、黑麦和小黑麦上的黑麦喙孢(Rhynchosporium secalis);
●油菜和向日葵上的核盘菌(Sclerotinia)属;
●小麦上的小麦壳针孢(Septoria tritici)和颖枯壳多孢(Stagonosporanodorum),
●葡萄藤上的葡萄钩丝壳(Erysiphe(同义词Uncinula)necator),
●玉米和草坪上的Setospaeria属,
●玉米上的丝轴黑粉菌(Sphacelotheca reilinia),
●大豆和棉花上的根串珠霉(Thievaliopsis)属,
●禾谷类上的腥黑粉菌(Tilletia)属,
●禾谷类、玉米和甘蔗上的黑粉菌(Ustilago)属(例如玉米上的玉蜀黍黑粉菌(U.maydis));
●苹果和梨上的黑星菌(Venturia)属(黑星病)(例如苹果上的苹果黑星菌(V.in aequalis))。
化合物I还适于防治有害真菌以保护材料(如木材、纸张、漆分散体、纤维或织物)和保护储藏的产品。在木材保护中,下列有害真菌值得注意:子囊菌纲真菌,如Ophiostoma spp.,长喙壳属(Ceratocystis spp.),出芽短梗霉(Aureobasidium pullulans),Sclerophoma spp.,毛壳属(Chaetomiumspp.),腐质霉属(Humicola spp.),彼得壳属(Petriella spp.),毛束霉属(Trichurus spp.);担子菌纲真菌,如粉孢革菌属(Coniophora spp.),革盖菌属(Coriolus spp.),粘褶菌属(Gloeophyllum spp.),香菇属(Lentinus spp.),侧耳属(Pleurotus spp.),卧孔菌属(Poria spp.),干朽菌属(Serpula spp.)和干酪菌属(Tyromyces spp.),半知菌纲真菌,如曲霉属(Aspergillus spp.),枝孢属(Cladosporium spp.),青霉属(Penicillium spp.),木霉属(Trichoderma spp.),链格孢属(Alternaria spp.),拟青霉属(Paecilomycesspp.)和接合菌纲(Zygomycetes)真菌,如毛霉属(Mucor spp.),此外,在保护储藏材料中下列酵母真菌值得注意:假丝酵母属(Candida spp.)和酿酒酵母(Saccharomyces cerevisae)。
化合物I可以通过用杀真菌有效量的活性化合物处理真菌或需要防止真菌侵袭的植物、种子、材料或土壤而使用。施用可以在材料、植物或种子被真菌侵染之前和之后进行。
杀真菌组合物通常包含0.1-95重量%,优选0.5-90重量%的活性化合物。活性化合物以90-100%,优选95-100%的纯度使用(根据NMR谱)。
当用于植物保护时,施用量取决于所需效果的种类为0.01-2.0kg活性化合物/公顷。
在例如通过撒粉、包衣或浸液进行的种子处理中,每100kg种子通常要求的活性化合物量为1-1000g,优选5-100g。
当用于保护材料或储藏产品时,活性化合物的施用量取决于施用区域的类型和所需效果。在保护材料中通常施用的量例如每m3处理材料为0.001g-2kg,优选0.005g-1kg活性化合物。
此外,式I化合物还适于有效防治选自昆虫、蜘蛛类和线虫类的害虫。它们可以在作物保护中以及在卫生领域和储存产品保护领域和兽医领域中用作杀虫剂。
它们通过接触而起作用或者可以通过胃起作用,或者具有内吸或残留作用。接触作用是指通过使害虫与化合物I或释放化合物I的材料接触而将其杀灭。通过胃起作用是指若害虫摄取杀虫有效量的化合物I或含有杀虫有效量的化合物I的材料,则其被杀灭。内吸作用是指化合物被吸收到被处理植物的植物组织中并且若害虫吃到植物组织或吸取植物汁液,则该害虫被防治。化合物I尤其适于防治下列昆虫害虫,如
昆虫:
鳞翅目(Lepidoptera)昆虫,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)、南部灰翅夜蛾(Spodoptera eridania)、草地夜蛾(Spodoptera frugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoea pityocampa、绿色橡木飞蛾(Tortrixviridana)、粉纹夜蛾(Trichoplusia ni)和Zeiraphera canadensis;鞘翅目(Coleoptera)昆虫(甲虫),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)、Diabrotica longicornis、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(Ipstypographus)、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 sp.)、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 japonica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilusgranaria);
双翅目(Diptera)昆虫,例如埃及伊蚊(Aedes aegypti)、剌扰伊蚊(Aedesvexans)、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);
缨翅目(Thysanoptera)昆虫(蓟马),例如兰花蓟马属(Dichromothrips spp.)、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(Thripsoryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci);膜翅目(Hymenoptera)蚂蚁、蜜蜂、黄蜂、锯蝇,例如新疆菜叶蜂(Athaliarosae)、切叶蚁(Atta cephalotes)、Atta laevigata、Atta robusta、Attacapiguara、Atta sexdens、Atta texana、举腹蚁属(Crematogaster)、Hoplocampa minuta、Hoplocampa testudinea、小黄家蚁(Monomoriumpharaonis)、热带火蚁(Solenopsis geminate)和红火蚁(Solenopsis invicta)、黑火蚁(Solenopsis richteri)、南方火蚁(Solenopsis xyloni)、红蚂蚁(Pogonomyrmex barbatus)、Pogonomyrmex californicus、Pheidolemegacephala、天鹅绒蚂蚁(Dasymutilla occidentalis)、熊蜂属(Bombusspp.)、大黄蜂(Vespula squamosa)、Paravespula vulgaris、Paravespulapennsylvanica、Paravespula germanica、姬胡蜂(Dolichovespula maculata)、黄边胡蜂(Vespa crabro)、胡蜂(Polistes rubiginosa)、Campodontusfloridanus和阿根廷蚁(Linepithema humile);
同翅目(Homoptera)昆虫,例如Acyrthosiphon onobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、豆蚜(Aphis craccivora)、甜菜蚜(Aphisfabae)、草莓根蚜(Aphis forbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphisgossypii)、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(Aulacorthum solani)、Bemisa tabaci、木薯粉虱(Bemisa argentifolii)、Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycauduspersicae、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosipha gossypii、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、Dysaphis plantaginea、Dysaphis pyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzuslactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphumeuphorbiae)、蔷薇管蚜(Macrosiphon rosae)、Megoura viciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophium dirhodum)、Myzodespersicae、冬葱瘤额蚜(Myzus ascalonicus)、Myzus cerasi、李瘤蚜(Myzusvarians)、Nasonovia ribis-nigri、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigus bursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodon humuli)、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)、白粉虱(Trialeurodesvaporariorum)、Toxoptera au rantiiand和葡萄根瘤蚜(Viteus vitifolii),等翅目昆虫(Isoptera)(白蚁),例如Calotermes flavicollis、金黄异白蚁(Heterotermes aureus)、Leucotermes flavipes、北美散白蚁(Reticulitermesflavipes)、美小黑散白蚁(Reticulitermes virginicus)、欧洲散白蚁(Reticulitermes lucifugus)和Termes natalensis,以及台湾乳白蚁(Coptotermes formosanus),
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 japonica)、棕色蜚蠊(Periplaneta brunnea)、Periplanetafuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blattaorientalis),
臭虫(半翅目(Hemiptera)),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercuscingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygaster integriceps)、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(Lygus pratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubea insularis、Thyanta perditor、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(Aulacorthum solani)、银叶粉虱(Bemisiaargentifolii)、Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycaudus persicae、Brachycaudus prunicola、甘蓝蚜(Brevicorynebrassicae)、Capitophorus horni、Cerosipha gossypii、Chaetosiphonfragaefolii、Cryptomyzus ribis、高加索冷杉椎球蚜(Dreyfusianordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphisradicola)、Dysaulacorthum pseudosolani、Dysaphis plantaginea、Dysaphispyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphon rosae)、Megouraviciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophiumdirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzus ascalonicus)、Myzuscerasi、李瘤蚜(Myzus varians)、Nasonovia ribis-nigri、稻飞虱(Nilaparvatalugens)、囊柄瘿绵蚜(Pemphigus bursarius)、蔗飞虱(Perkinsiellasaccharicida)、忽布疣蚜(Phorodon humuli)、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)、Schizoneura lanuginosa、麦长管蚜(Sitobionavenae)、白粉虱(Trialeurodes vaporariorum)、Toxoptera aurantiiand、葡萄根瘤蚜(Viteus vitifolii)、Cimex lectularius、Cimex hemipterus、Reduviussenilis、Triatoma属和Arilus critatus,
(直翅目(Orthoptera))的蟋蟀、蚱蜢、蝗虫,例如居屋艾蟋(Achetadomestica)、东方蜚蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、意大利蝗(Calliptamus italicus)、澳洲草栖蝗(Chortoicetes terminifera)、摩洛哥戟纹蝗(Dociostaurus maroccanus)、欧洲球螋(Forficula auricularia)、蝼蛄(Gryllotalpa gryllotalpa)、非洲蔗蝗(Hieroglyphus daganensis)、Kraussaria angulifera、飞蝗(Locusta migratoria)、褐色拟飞蝗(Locustanapardalina)、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)、塞纳加尔小车蝗(Oedaleus senegalensis)、美洲蟑螂(Periplaneta americana)、美洲沙漠蝗(Schistocerca americana)、Schistocerca peregrina、沙漠蝗(Schistocerca gregaria)、Stauronotusmaroccanus和庭疾灶螽(Tachycines asynamorus)、庭疾灶螽(Tachycinesasynamorus)、Zonozerus variegatus。
式I化合物及其盐还可以用于防治蜘蛛(蜘蛛纲(Arachnoidea)),如螨(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)、Ambryomma maculatum、波斯锐缘蜱(Argaspersicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、Dermacentor andersoni、Dermacentor variabilis、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、Ixodes scapularis、Ixodes holocyclus、Ixodes pacificus、Ornithodorus hermsi、Ornithodorus turicata、Ornithonyssus bacoti、Ornithodorus moubata、Otobius megnini、鸡皮刺螨(Dermanyssusgallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalus sanguineus、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptesscabiei),瘿螨(Eriophyidae)属,如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨(Tarsonemidae)属,如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨(Ten uipalpidae)属,如紫红短须螨(Brevipalpus phoenicis);叶螨(Tetranychidae)属,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;蜘蛛目(Araneida),例如毒蜘蛛(Latrodectus mactans)和褐丝蛛(Loxoscelesreclusa),
蚤(蚤目(Siphonaptera)),例如猫蚤(Ctenocephalides felis)、狗蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulexirritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyllus fasciatus),衣鱼、家衣鱼(缨尾目(Thysanura)),例如西洋衣鱼(Lepisma saccharina)和斑衣鱼(Thermobia domestica),
百足虫(唇足纲(Chilopoda)),例如Scutigera coleoptrata,
千足虫(倍足纲(Diplopoda)),例如Narceus属,
蠼蛸(革翅目(Dermaptera)),例如forficula auricularia,
虱(Phthiraptera),例如Pediculus humanus capitis、Pediculus humanuscorporis、阴虱(Pthirus pubis)、Haematopinus eurysternus、Haematopinussuis、Linognathus vituli、Bovicola bovis、Menopon gallinae、Menacanthusstramineus和Solenopotes capillatus。
杀虫组合物通常包含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。
在室外条件下,对防治害虫而言活性化合物的施用率为0.1-2.0kg/ha,优选0.2-1.0kg/ha。
可以将化合物I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。施用形式取决于特定的意欲目的;在每种情况下都应确保本发明化合物精细和均匀地分布。
配制剂以已知方式制备,例如通过将活性化合物与溶剂和/或载体混合而制备,若需要的话使用乳化剂和分散剂。合适的溶剂/助剂主要为:
-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、N-辛基吡咯烷酮、)、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。
-载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂为木素磺酸、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。
还可以将防冻剂如甘油、乙二醇和丙二醇加入配制剂中。
合适的消泡剂例如为基于聚硅氧烷或硬脂酸镁的那些。
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。
种子处理用配制剂可以额外包含粘合剂和/或胶凝剂和合适的话着色剂。
可加入粘合剂以改进在处理之后活性化合物在种子上的附着。合适的粘合剂为EO/PO嵌段共聚物表面活性剂以及聚乙烯醇、聚乙烯吡咯烷酮、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(Lupasol,Polymin)、聚醚、聚氨酯、聚乙酸乙烯酯、纤基乙酸钠以及这些聚合物的共聚物。
合适的胶凝剂例如为角叉菜(Satiagel)。
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。
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%,优选0.01-1%。
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。
对于种子处理,所述配制剂在稀释2-10倍后得到活性化合物在即用制剂中的浓度为0.01-60重量%,优选0.1-40重量%。
下列为配制剂实例:
1.用水稀释的产品
A)水溶性浓缩物(SL、LS)
将10重量份本发明化合物I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。以此方式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重量份本发明化合物I溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯吡咯烷酮。用水稀释得到分散体。活性化合物含量为20重量%。
C)乳油(EC)
将15重量份本发明化合物I溶于75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。该配制剂的活性化合物含量为15重量%。
D)乳液(EW、EO、ES)
将25重量份本发明化合物I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。该配制剂的活性化合物含量为25重量%。
E)悬浮液(SC、OD)
在搅拌的球磨机中,在加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂下将20重量份本发明化合物I粉碎,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。该配制剂中的活性化合物含量为20重量%。
F)水分散性颗粒和水溶性颗粒(WG、SG、SS、WS)
在加入50重量份分散剂和湿润剂下将50重量份本发明化合物I细碎研磨,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。该配制剂的活性化合物含量为50重量%。
G)水分散性粉末和水溶性粉末(WP、SP)
在加入25重量份分散剂、湿润剂和硅胶下将75重量份本发明化合物I在转子-定子磨机中研磨。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为75重量%。
2.不经稀释而施用的产品
H)可撒粉粉末(DP、DS)
将5重量份本发明化合物I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重量份本发明化合物I细碎研磨并结合99.5重量份载体。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活性化合物含量为0.5重量%的颗粒。
K)ULV溶液(UL、LS)
将10重量份本发明化合物I溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而施用的活性化合物含量为10重量%的产品。
活性化合物可以直接、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;在每种情况下本发明应确保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。或者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可能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%,优选0.01-1%。
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。
可以将各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂加入活性化合物中,合适的话恰在紧临使用之前加入(桶混合)。这些试剂可以1∶10-10∶1的重量比与本发明试剂混合。
在作为杀真菌剂的使用形式中,本发明组合物还可与其它活性化合物一起存在,例如与除草剂、杀虫剂、生长调节剂、杀真菌剂或肥料一起存在。将化合物I或包含它们的组合物以杀真菌剂使用形式与其它杀真菌剂混合在许多情况下导致杀真菌活性谱的拓宽。
本发明化合物可以与其一起使用的下列杀真菌剂用于说明可能的组合但不限制它们:
·酰基丙氨酸类,例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)或霜灵(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)、螺茂胺(spiroxamine)或克啉菌(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(cycloheximide)、灰黄霉素(griseofulvin)、春雷霉素(kasugamycin)、多马霉素(natamycin)、多氧霉素(polyoxin)或链霉素(streptomycin),
·唑类,例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(dinitroconazole)、烯菌灵(enilconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑醇(ipconazole)、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)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizole)或戊叉唑菌(triticonazole),
·二羧酰亚胺类,如异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)或烯菌酮(vinclozolin),
·二硫代氨基甲酸盐类,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)或代森锌(zineb),
·杂环化合物,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)、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)、氟吡菌胺(picobenzamide)、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(thifluzamide)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)或嗪氨灵(triforine),
·铜杀真菌剂,如波尔多液(Bordeaux混合物)、醋酸铜、王铜(copperoxychloride)或碱式硫酸铜,
·硝基苯基衍生物,如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)或异丙消(nitrophthal-isopropyl),
·苯基吡咯类,如拌种咯(fenpiclonil)或氟菌(fludioxonil),
·硫,
·其它杀真菌剂,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(ethaboxam)、环酰菌胺(fenhexamid)、薯瘟锡(fentin acetate)、氰菌胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、藻菌磷(fosetyl)、藻菌磷(fosetyl-aluminum)、亚磷酸、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、苯菌酮(metrafenone)、戊菌隆(pencycurone)、吡噻菌胺(penthropyrad)、百维灵(propamocarb)、四氯苯酞(phthalide)、甲基立枯磷(tolclofos-methyl)、五氯硝基苯(quintozene)或苯酰菌胺(zoxamide),
·嗜球果伞素类,如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、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)、唑菌胺酯(pyraclostrobin)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)或对甲抑菌灵(tolylfluanid),
·肉桂酰胺及类似化合物,如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
本发明的杀虫组合物还可以含有其他活性成分,例如其他农药如杀虫剂和除草剂,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,合适的话还可在紧临使用前加入(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对植物喷雾。
这些试剂通常以1∶100-100∶1的重量比与本发明试剂混合。
本发明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:
A.1.有机(硫代)磷酸酯类:例如高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(chlorfenvinphos)、二嗪农(diazinon)、敌敌畏(dichlorvos)、百治磷(dicrotophos)、乐果(dimethoate)、乙拌磷(disulfoton)、乙硫磷(ethion)、杀螟松(fenitrothion)、倍硫磷(fenthion)、异唑磷(isoxathion)、马拉硫磷(malathion)、甲胺磷(meth amidophos)、杀扑磷(methidathion)、甲基一六零五(methyl-parathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、砜吸磷(oxydemeton-methyl)、对氧磷(paraoxon)、一六零五(parathion)、稻丰散(phenthoate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、甲拌磷(phorate)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、丙硫磷(prothiofos)、乙丙硫磷(sulprophos)、杀虫威(tetrachlorvinphos)、特丁磷(terbufos)、三唑磷(triazophos)、敌百虫(trichlorfon);
A.2.氨基甲酸酯类:例如棉铃威(alanycarb)、涕灭威(aldicarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、双氧威(fenoxycarb)、呋线威(furathiocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、唑蚜威(triazamate);
A.3.合成除虫菊酯类:例如丙烯除虫菊(allethrin)、氟氯菊酯(bifenthrin)、氟氯氰菊酯(cyfluthrin)、(RS)氯氟氰菊酯(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)、己体氯氰菊酯(zeta-cypermethrin)、溴氰菊酯(deltamethrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、咪炔菊酯(imiprothrin)、氯氟氰菊酯(lambda-cyhalothrin)、氯菊酯(permethrin)、炔酮菊酯(prallethrin)、除虫菊酯I(pyrethrin I)和除虫菊酯II、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、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);
A.4.生长调节剂:a)几丁质合成抑制剂:例如苯甲酰脲类,如定虫隆(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)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(buprofezin)、茂醚(diofenolan)、噻螨酮(hexythiazox)、特苯唑(etoxazole)、四螨嗪(clofentazine);b)蜕皮激素拮抗剂:例如特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、艾扎丁(azadirachtin);c)保幼激素类似物:例如蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)、双氧威(fenoxycarb);d)类脂生物合成抑制剂:例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)或螺虫乙酯(spirotetramat);
A.5.烟碱性受体激动剂/拮抗剂化合物(烟碱杀虫剂或新烟碱类):例如噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、吡虫清(acetamiprid)、噻虫啉(thiacloprid)或式P1的噻唑化合物:
A.6.GABA拮抗剂化合物:例如acetoprole、硫丹(endosulfan)、乙虫腈(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole)、pyrafluprole、pyriprole、5-氨基-3-(氨基硫羰基)-1-(2,6-二氯-4-三氟甲基苯基)-4-(三氟甲基亚硫酰基)吡唑;
A.7.大环内酯杀虫剂:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin)、米尔螨素(milbemectin)、lepimectin、艾克敌105(spinosad);
A.8.线粒体配合物I电子输送抑制剂(METI I化合物):例如喹螨醚(fenazaquin)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、flufenerim;
A.9.线粒体配合物II和/或配合物III电子输送抑制剂(METI II和III化合物):例如灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
A.10.解偶联剂化合物:例如氟唑虫清(chlorfenapyr);
A.11.氧化磷酸化抑制剂化合物:三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite);
A.12.蜕皮干扰剂(Moulting disruptor)化合物:例如cryomazine;
A.13.混合功能氧化酶抑制剂化合物:例如增效醚(piperonyl butoxide);
A.14.钠通道阻断剂化合物:例如二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
A.15.其他各种:benclothiaz、联苯肼酯(bifenazate)、杀螟丹(cartap)、氟啶虫酰胺(flonicamid)、啶虫丙醚(pyridalyl)、据嗪酮(pymetrozine)、硫、硫环杀(thiocyclam)、氟虫酰胺(flubendiamide)、cyenopyrafen、吡氟硫磷(flupyrazofos)、丁氟螨酯(cyflumetofen)、amidoflumet、式P2化合物:
其中X和Y各自独立地为卤素,尤其是氯;
W为卤素或C1-C2卤代烷基,尤其是三氟甲基;
R1为C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C4烷氧基-C1-C4烷基或C3-C6环烷基,它们各自可以被1、2、3、4或5个卤原子取代,特别地,R1为甲基或乙基;
R2和R3为C1-C6烷基,尤其是甲基,或者可以与相邻碳原子一起形成C3-C6环烷基结构部分,尤其是环丙基结构部分,其可以带有1、2或3个卤原子,例如包括2,2-二氯环丙基和2,2-二溴环丙基;和
R4为氢或C1-C6烷基,尤其是氢、甲基或乙基;
式P3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,以及RB为氢、CH3或CH(CH3)2;
以及JP 2002284608、WO 02/89579、WO 02/90320、WO 02/90321、WO04/06677、WO 04/20399或JP 2004/99597中所述的丙二腈化合物。
合适的农药化合物还包括微生物如苏芸金芽孢杆菌(Bacillusthuringiensis)、Bacillus tenebrionis和枯草芽孢杆菌(Bacillus subtilis)。
上述组合物特别可以用于保护植物以免被所述害虫侵染并且还保护植物以免被植物病原性真菌侵染或在侵袭/侵染的植物中对抗这些害虫/真菌。
然而,式I化合物还适于处理种子。对种子的施用在播种之前进行,直接在种子上进行或者在种子催芽之后进行。
可以用于种子处理的组合物例如为:
A可溶性液剂(SL、LS)
D乳液(EW、EO、ES)
E悬浮液(SC、OD、FS)
F水分散性颗粒和水溶性颗粒(WG、SG)
G水分散性粉末和水溶性粉末(WP、SP、WS)
H可撒粉粉末(DP、DS)
用于种子处理的优选式I化合物FS配制剂通常包含0.5-80%活性成分,0.05-5%润湿剂,0.5-15%分散剂,0.1-5%增稠剂,5-20%防冻剂,0.1-2%消泡剂,1-20%颜料和/或染料,0-15%粘着剂/粘合剂,0-75%填料/赋形剂和0.01-1%防腐剂。
用于种子处理配制剂的合适颜料或染料是颜料蓝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。
加入粘着剂/粘合剂以改进在处理之后活性物质在种子上的附着。合适的粘合剂为EO/PO嵌段共聚物表面活性剂以及聚乙烯醇、聚乙烯吡咯烷酮、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(Lupasol,Polymin)、聚醚以及衍生于这些聚合物的共聚物。
为了用于对抗蚂蚁、白蚁、黄蜂、蝇、蚊、蟋蟀或蟑螂,优选将式I化合物用于诱饵组合物中。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。固体诱饵可以制成各种适合相应应用的形状和形式,如颗粒、块、棒、片。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。凝胶可以基于水性基质或油性基质且可以按照粘性、水分保留或老化特性发明的特定要求配制。
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、蟋蟀等昆虫或蟑螂食用它的产品。可以通过使用进食刺激剂或性信息素控制吸引力。食物刺激剂例如选自但不限于动物和/或植物蛋白质(肉-、鱼-或血液食物,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。特定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。
气雾剂(例如在喷雾罐中)、油喷雾剂或泵喷雾剂形式的式I化合物配制剂高度适于非专业使用者来防治害虫如蝇、蚤、蜱、蚊或蟑螂。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),沸点范围为约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,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化合物及其相应的组合物还可以用于蚊香片和熏蒸片,烟雾筒、蒸发器板或长效蒸发器以及扑蛾纸(moth paper)、扑蛾垫(moth ped)或其他与非热依赖型蒸发器体系中。
式I化合物及其组合物可以用于保护非活体材料,尤其是基于纤维素的材料,如木质材料,例如树木、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(half board)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。
在本发明方法中,通过使目标寄生虫/害虫、其食物源、栖息地、繁殖地或其场所与杀虫有效量的至少一种化合物I或其N-氧化物或盐或含有杀虫有效量的至少一种化合物I或其N-氧化物或盐的组合物接触而防治害虫。
“场所”是指害虫或寄生虫生长或可能生长于其中的栖息地、繁殖地、植物、种子、土壤、区域、材料或环境。
通常,“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。
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植物以免被害虫侵袭或侵染。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)。
通过用杀真菌或杀虫有效量的至少一种活性化合物I、其N-氧化物或盐处理真菌、害虫或需要防止真菌侵袭或害虫侵袭的植物、种子、材料或土壤而使用化合物I。施用可以在材料、植物或种子被真菌或害虫侵袭/侵染之前和之后进行。
当用于植物保护时,施用量取决于所需效果的种类为0.1-4000g/公顷,理想的是25-600g/公顷,更理想的是50-500g/公顷。
在种子处理中,活性化合物的施用率通常为0.001-100g/kg种子,优选0.01-50g/kg种子,尤其是0.01-2g/kg种子。
在土壤处理或施用于害虫住所或巢穴的情况下,活性成分的量为0.0001-500g/100m2,优选0.001-20g/100m2。
在材料保护中的常规施用率例如基于每m2被处理材料为0.01-1000g活性化合物,理想的是0.1-50g。
用于浸渍材料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。
对于在诱饵组合物中使用,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。
对于在喷雾组合物中使用,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%。
当用于保护材料或储存产品时,活性化合物的施用量取决于施用区域的类型和所需效果。在材料保护中的通常施用量例如基于每m3被处理材料为0.001g-2kg活性化合物,优选0.005g-1kg活性化合物。
在室外条件下,用于防治害虫的活性化合物施用率为0.1-2.0kg/ha,优选0.2-1.0kg/ha。
各种类型的油、湿润剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂都可加入活性化合物中,若合适的话,恰在紧临使用前加入(桶混物)。这些试剂可与本发明试剂以1∶100-100∶1,优选1∶10-10∶1的重量比混合。
可以使用的辅助剂尤其为有机改性的聚硅氧烷,例如Break ThruS 240;醇烷氧基化物,例如Atplus 245、Atplus MBA 1303、PlurafacLF 300和Lutensol ON 30;EO/PO嵌段聚合物,例如Pluronic RPE 2035和Genapol B;醇乙氧基化物,例如Lutensol XP 80;以及二辛基磺基琥珀酸钠,例如Leophen RA。
式I化合物、其N-氧化物和可兽用盐以及包含它们的组合物还可以用于在包括温血动物(包括人)在内的动物和鱼中控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、骆驼、鹿、马、小猪、家禽、兔、山羊、狗和猫,水牛、驴、黇鹿(fallow deer)和驯鹿,以及裘皮用动物如貂、丝鼠和浣熊,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、鲤鱼和鳗鱼的动物中控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。
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。
对于温血动物的口服给药,可以将式I化合物配制成动物饲料、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化合物可以在其饮用水中给药于动物。对于口服给药,所选剂型应为动物提供基于每kg动物体重为0.01-100mg/天,优选0.5-100mg/天的式I化合物。
另外,式I化合物、其N-氧化物和盐可以肠胃外给药于动物,例如通过intraruminal、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。另外,可以将式I化合物配制成皮下给药用植入物。此外,式I化合物可以经皮给药于动物。对于肠胃外给药,所选剂型应为动物提供基于每kg动物体重为0.01-100mg/天的式I化合物。
式I化合物还可以浸液、粉剂、粉末、套环、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、喷林配制剂、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。
通常有利的是施用以10-300mg/kg,优选20-200mg/kg的总量释放式I化合物的固体配制剂。
活性化合物还可以与协同增效剂或对病原性体内和体外寄生虫起作用的其他活性化合物混合使用。
通常而言,式I化合物以杀寄生虫有效量施用,该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寄生虫效果及持续时间、目标物种、施用方式等而变化。
合成实施例
通过适当改变起始化合物,使用下列合成实施例中所述程序制备其他化合物I。如此得到的化合物与物理数据一起列于下表中。
实施例1:N-(吡啶-4-基甲基)-4′-氰基联苯-4-磺酰胺的制备
将0.73g三乙胺加入2g 4’-氰基联苯-4-磺酰氯(参见EP-A 483 667)在80mL乙醚中的溶液中,然后加入0.78g 4-(氨基甲基)吡啶在15mL二烷中的溶液中。在约23℃下搅拌18小时后,蒸除溶剂并将残余物在硅胶上进行色谱法(甲基叔丁基醚[MtBE]/甲醇混合物)。得到0.9g熔点为198-202℃的标题化合物。
实施例2:N-(吡啶-4-基甲基)-2′-氯联苯-4-磺酰胺的制备2a:4-碘-N-吡啶-4-基甲基苯基磺酰胺
在0-5℃下将7mL吡啶加入50g 4-碘苯基磺酰氯在400mL乙醚中的溶液中,然后滴加17.8g 4-(氨基甲基)吡啶在20mL二烷中的溶液。在23℃下搅拌18小时后,滤出沉淀,用稀NaHCO3溶液洗涤,然后干燥。得到29.9g熔点为174-176℃的标题化合物。
2b:N-(吡啶-4-基甲基)-2′-氯联苯-4-磺酰胺
向5g来自实施例2a的磺酰胺在200mL四氢呋喃(THF)中的溶液中加入4.2g 2-氯苯基硼酸,随后加入7.1g Na2CO3在100mL水中的溶液。加入1g乙酸钯和约100mg Pd[P(苯基)]3之后,将该混合物在回流下加热5小时,然后加入水中。在用甲基叔丁基醚萃取之后,将有机相用水洗涤,然后干燥并除去溶剂。在硅胶上对残余物进行色谱法(甲基叔丁基醚/甲醇混合物)之后得到3.8g熔点为138-141℃的标题化合物。
实施例3:4′-氰基联苯-4-(磺酸)-(2-甲氧基吡啶-4-基甲基)酰胺的制备3a:2-甲氧基异烟腈
在5-10℃下将60g(0.433mol)2-氯异烟腈在200mL二甲基甲酰胺中的溶液滴加到在100mL二甲基甲酰胺中的25g(0.46mol)固体甲醇钠中。然后将该混合物在5℃下搅拌2小时,然后在23℃下搅拌12小时。将反应混合物倾于水上,然后用甲基叔丁基醚萃取。合并的有机相用水洗涤并干燥。减压除去溶剂。产量:47.5g有用产物。
1H-NMR(CDCl3):δ[ppm]=4.0(s),6.9(s),7.9(m)和8.3(m)。3b:C-(2-甲氧基吡啶-4-基)甲基胺
将57.5g(0.42mol)来自3a的2-甲氧基异烟腈在1000mL乙醇中的溶液用500mL 25%氨水溶液处理。然后在14g Pd/C(10%)存在下于0-5℃和0.1巴的压力下氢化7小时。在过滤并除去溶剂之后,将残余物溶于二氯甲烷中。然后用水洗涤,干燥并减压除去溶剂。将残余物在硅胶上用甲基叔丁基醚进行色谱法。产量:17g油状有用产物。
1H-NMR(CDCl3):δ[ppm]=3.7(s),3.9(s),6.7(s),6.8(m)和8.1(m)。3c:4-碘-N-(2-甲氧基吡啶-4-基甲基)苯磺酰胺
在0-5℃下,将在150mL乙腈中的40g(0.29mol)来自实施例3b的C-(2-甲氧基吡啶-4-基)甲基胺与29.4g(0.29mol)三乙胺混合。向其中滴加79.7g(0.263mol)4-碘苯基磺酰氯在300mL乙腈中的溶液,并将该混合物在23℃下搅拌18小时。然后过滤混合物并蒸发滤液。将残余物与水混合并搅拌4小时。滤出所得产物,然后用少量二氯甲烷洗涤并干燥。产量:43g有用产物。
1H-NMR(d6-二甲亚砜):δ[ppm]=3.8(s),4.0(s),7.5(m),7.9(m)和8.4(m)。3d:4′-氰基联苯-4-(磺酸)-(2-甲氧基吡啶-4-基甲基)酰胺
将25g(0.061mol)来自实施例3c的4-碘-N-(2-甲氧基吡啶-4-基甲基)苯磺酰胺在300mL四氢呋喃中的溶液与18.18g(0.122mol)4-氰基苯基硼酸混合,然后与在130mL水中的32.8g(0.30mol)碳酸钠混合。在加入0.6g[1,4-二(二苯基膦基)丁烷]氯化钯(II)之后,将该混合物回流2小时,然后加入水中。在用甲基叔丁基醚萃取之后,将有机相用水洗涤,然后干燥并除去溶剂。将残余物用少量二氯甲烷搅拌,分离并干燥。产量:20.4g有用产物;熔点:120-125℃。
实施例4:4′-氯联苯-4-(磺酸)-(3-甲氧基吡啶-4-基甲基)酰胺的制备4a:3-甲氧基异烟腈
在5℃下将62.8g(0.453mol)3-氯异烟腈(其制备参见J.HeterocyclicChem.15,683(1978))在200mL二甲基甲酰胺中的溶液滴加到在100mL二甲基甲酰胺中的26.3g(0.48mol)固体甲醇钠中。然后将该混合物在5℃下搅拌2小时,再在23℃下搅拌18小时。将反应溶液倾于水上,然后用甲基叔丁基醚萃取。将合并的有机相用水洗涤,干燥并减压除去溶剂。产量:39.5g有用产物。
1H-NMR(CDCl3):δ[ppm]=4.0(s),7.5(m),8.4(m)和8.5(s)。4b:C-(3-甲氧基吡啶-4-基)甲基胺
将34g(0.254mol)来自实施例4a的3-甲氧基异烟腈在1000mL乙醇中的溶液用336mL 25%氨水溶液处理,然后在18g Pd/C(10%)存在下于0-5℃和0.1巴的压力下氢化6.5小时。然后滤除固体,将滤液蒸发。将残余物溶于二氯甲烷中。将有机相用水洗涤一次,然后干燥并最后减压除去溶剂。使用甲基叔丁基醚作为溶剂在硅胶上进行色谱法之后,得到26.9g油形式的有用产物。
1H-NMR(CDCl3):δ[ppm]=3.7(s),3.9(s),7.2(m)和8.3(m)。4c:4′-氯联苯-4-(磺酸)-(3-甲氧基吡啶-4-基甲基)酰胺
在0-5℃下将在100mL乙腈中的8g(0.059mol)来自实施例4b的C-(3-甲氧基吡啶-4-基)甲基胺与5.9g(0.057mol)三乙胺混合。向其中滴加15.15g(0.052mol)4′-氯联苯-4-磺酰氯在100mL乙腈中的溶液。然后再将反应混合物在23℃下搅拌18小时,然后滤除固体。蒸发滤液。将残余物与水/正戊烷搅拌7小时。然后分离固体部分,用少量甲基叔丁基醚洗涤并干燥。产量:14.3g有用产物;熔点:127-131℃。
实施例5:2,2,4′-三氟联苯-4-(磺酸)-(吡啶-4-基甲基)酰胺的制备5a:4-溴-3-氟-N-吡啶-4-基甲基苯磺酰胺
将在80mL乙腈中的2.17g(0.020mol)吡啶甲胺在0-5℃下与2g(0.020mol)三乙胺混合。向其中滴加15.15g(0.052mol)4-溴-3-氟苯基磺酰氯在20mL乙腈中的溶液。然后再将反应混合物在23℃下搅拌18小时,然后蒸发。将残余物与水混合。搅拌3小时后分离出固体部分,用正戊烷洗涤并干燥。产量:6.1g有用产物。
1H-NMR(d6-二甲亚砜):δ[ppm]=4.1(s),7.2(s),7.6(m),7.7(m),7.9(m),8.5(m)和8.6(m)。
5b:2,2,4′-三氟联苯-4-(磺酸)-(吡啶-4-基甲基)酰胺
将0.5g(1.4mmol)来自实施例5a的4-溴-3-氟-N-吡啶-4-基甲基苯磺酰胺在80mL四氢呋喃中的溶液与0.46g(2.9mmol)2,4-二氟苯基硼酸混合,然后与在30mL水中的0.78g(7.2mmol)碳酸钠混合。在加入0.1g[1,4-二(二苯基膦基)丁烷]氯化钯(II)之后,将该混合物回流5小时,然后加入水中。在用甲基叔丁基醚萃取之后,将有机相用水洗涤,然后干燥并除去溶剂。将残余物用甲基叔丁基醚在硅胶上进行色谱法。产量:90mg有用产物。
1H-NMR(d6-二甲亚砜):δ[ppm]=4.2(s),7.2(m),7.4-7.7(m),8.4(m)和8.6(m)。
已经制备或可以按类似于实施例1-5中所述程序制备的其他联苯磺酰胺I列于下表B)和C)中:
表B)-式I’化合物
表C)-式I化合物(R1=H)
序号 | (R7)n | (R6)m | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];MSM+H+[m/e]RT[min];1H-NMR[ppm] |
1-1 | - | - | CF3 | H | H | H | 155-157 |
1-2 | - | - | H | OCH3 | H | H | 105-109 |
1-3 | 4-Cl | - | H | OCH3 | H | H | 127-130 |
1-4 | 4-C(O)CH3 | - | H | OCH3 | H | H | 98-100 |
1-5 | 4-C(CH3)=NOCH3 | - | H | OCH3 | H | H | 350.10 |
1-6 | 4-C(CH3)=NOCH2CH3 | - | H | OCH3 | H | H | 364.10 |
1-7 | - | - | Cl | H | Cl | H | 148-151 |
1-8 | 4-C(O)CH3 | - | Cl | H | Cl | H | 132-135 |
1-9 | - | - | CH3 | H | H | H | 133-135 |
1-10 | - | - | OCH3 | H | H | H | 187-189 |
1-11 | - | - | H | Cl | H | Cl | 165-167 |
1-12 | 4-F | - | OCH3 | H | H | H | 78-82 |
1-13 | 4-CN | - | OCH3 | H | H | H | 135-138 |
1-14 | 4-Cl | - | OCH3 | H | H | H | 170-174 |
1-15 | 4-CH3 | - | OCH3 | H | H | H | 2,7;369,15 |
序号 | (R7)n | (R6)m | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];MSM+H+[m/e]RT[min]);1H-NMR[ppm] |
I-16 | 3,5-Cl2 | - | OCH3 | H | H | H | 3,0;422,95 |
I-17 | 3,5-(CF3)2 | - | OCH3 | H | H | H | 3,1;491,05 |
I-18 | 4-CF3 | - | OCH3 | H | H | H | 2,89;423,05 |
I-19 | 3-Cl,4-F | - | OCH3 | H | H | H | 2,7;406,9 |
I-20 | 4-Br | - | OCH3 | H | H | H | 182-190 |
I-21 | 2-CH3 | - | OCH3 | H | H | H | 2,61;369 |
I-22 | 3,5-F2 | - | OCH3 | H | H | H | 2,66;391,05 |
I-23 | 2-F | - | OCH3 | H | H | H | 2,52;373,05 |
I-24 | 2,4-Cl2 | - | OCH3 | H | H | H | 2,94;422,95 |
I-25 | 2,4-F2 | - | OCH3 | H | H | H | 2,61;391,05 |
I-26 | 3-CH3-4-Cl | - | OCH3 | H | H | H | 2,95;403,05 |
I-27 | 4-OCH3 | - | OCH3 | H | H | H | 2,54;385,05 |
I-28 | 3-CH3 | - | OCH3 | H | H | H | 2,72;369,15 |
I-29 | 2-CH3-5-Br | - | OCH3 | H | H | H | 2,85;463,05 |
I-30 | 4-OCF3 | - | OCH3 | H | H | H | 2,97;439,05 |
I-31 | 3,5-(CH3)2 | - | OCH3 | H | H | H | 2,92;383,15 |
I-32 | 3,4-(OCH3)2 | - | OCH3 | H | H | H | 2,3;415,05 |
I-33 | 3-F | - | OCH3 | H | H | H | 2,57;373,05 |
I-34 | 2-CF3 | - | OCH3 | H | H | H | 2,71;423,05 |
I-35 | 4-CH2CH3 | - | OCH3 | H | H | H | 2,94;383,15 |
I-36 | 2,3-(CH3)2 | - | OCH3 | H | H | H | 2,83;383,15 |
I-37 | 2,5-(OCH3)2 | - | OCH3 | H | H | H | 2,54;415,15 |
I-38 | 2,5-(CH3)2 | - | OCH3 | H | H | H | 2,86;383,15 |
I-39 | 3-OCF3 | - | OCH3 | H | H | H | 2,85;438,9 |
序号 | (R7)n | (R6)m | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];MSM+H+[m/e]RT[min]);1H-NMR[ppm] |
I-40 | 3-OCF3 | - | OCH3 | H | H | H | 2,81;422,9 |
I-41 | 3-F,4-OCH3 | - | OCH3 | H | H | H | 2,50;403,0 |
I-42 | 3-F,5-OCH3 | - | OCH3 | H | H | H | 2,60;402,9 |
I-43 | 3-CH3,4-F | - | OCH3 | H | H | H | 2,77;387,05 |
I-44 | 4-OCH2CH3 | - | OCH3 | H | H | H | 2,73;399,05 |
I-45 | 3-Br | - | OCH3 | H | H | H | 2,81;434,85 |
I-46 | 3,4-F2 | - | OCH3 | H | H | H | 2,65;390,95 |
I-47 | 3,4-Cl2 | - | OCH3 | H | H | H | 2,98;422,85 |
I-48 | 3-OCH2CH3 | - | OCH3 | H | H | H | 2,72;399,00 |
I-49 | 2,5-Cl2 | - | OCH3 | H | H | H | 2,89;422,80 |
I-50 | 2,5-(OCH3)2 | - | OCH3 | H | H | H | 2,60;414,95 |
I-51 | 3-OCH3 | - | OCH3 | H | H | H | 2,58;384,95 |
I-52 | 3,5-Br2 | - | OCH3 | H | H | H | 3,16;512,75 |
I-53 | 2-OCH3-5-Cl | - | OCH3 | H | H | H | 2,82;418,95 |
I-54 | 2-F,4-Cl,5-CH3 | - | OCH3 | H | H | H | 3,05;420,85 |
I-55 | 2-CH3-4-F | - | OCH3 | H | H | H | 2,75;386,95 |
I-56 | 4-C(CH3)3 | - | OCH3 | H | H | H | 3,22;411,05 |
I-57 | 3,4-(-OCH2O-) | - | OCH3 | H | H | H | 2,48;398,95 |
I-58 | 2-F-4-Cl-5-OH | - | OCH3 | H | H | H | 2,26;404,85 |
I-59 | 2-F,4-Cl | - | OCH3 | H | H | H | 2,53;406,90 |
I-60 | 2-F,4-CH3 | - | OCH3 | H | H | H | 2,73;387,0 |
I-61 | 3,4-(-OCH2CH2O-) | - | OCH3 | H | H | H | 2,49;412,90 |
I-62 | 2,4-(OCF3)2 | - | OCH3 | H | H | H | 124 |
I-63 | 4-CN | - | H | OCH3 | H | H | 120-123 |
序号 | (R7)n | (R6)m | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];MSM+H+[m/e]RT[min]);1H-NMR[ppm] |
I-64 | 4-F | - | H | OCH3 | H | H | 123-129 |
I-65 | 2-OCH3 | - | H | OCH3 | H | H | 2,89;385,05 |
I-66 | 4-SCH3 | - | H | OCH3 | H | H | 3,10;400,90 |
I-67 | 4-CH3 | - | H | OCH3 | H | H | 3,11;369,15 |
I-68 | 3,5-Cl2 | - | H | OCH3 | H | H | 3,56;426,10 |
I-69 | 3,5-(CF3)2 | - | H | OCH3 | H | H | 3,62;491,05 |
I-70 | 4-CF3 | - | H | OCH3 | H | H | 3,30;423,05 |
I-71 | 3-Cl,4-F | - | H | OCH3 | H | H | 3,26;406,9 |
I-72 | 4-Br | - | H | OCH3 | H | H | 134-144 |
I-73 | 2-CH3 | - | H | OCH3 | H | H | 3,02;369,0 |
I-74 | 3,5-F2 | - | H | OCH3 | H | H | 3,06;391,05 |
I-75 | 2-F | - | H | OCH3 | H | H | 2,90;373,05 |
I-76 | 2,4-Cl2 | - | H | OCH3 | H | H | 3,40;423,05 |
I-77 | 2,4-F2 | - | H | OCH3 | H | H | 2,98;391,05 |
I-78 | 3-CH3,4-Cl | - | H | OCH3 | H | H | 3,41;403,05 |
I-79 | 4-OCH3 | - | H | OCH3 | H | H | 2,85;385,05 |
I-80 | 2,5-F2 | - | H | OCH3 | H | H | 2,96;391,05 |
I-81 | 3-CH3 | - | H | OCH3 | H | H | 3,11;369,15 |
I-82 | 2-OCH3,5-Br | - | H | OCH3 | H | H | 3,24;462,95 |
I-83 | 4-OCF3 | - | H | OCH3 | H | H | 3,38;439,05 |
I-84 | 3,5-(CH3)2 | - | H | OCH3 | H | H | 3,34;383,15 |
I-85 | 3,4-(OCH3)2 | - | H | OCH3 | H | H | 2,67;415,15 |
I-86 | 3-F | - | H | OCH3 | H | H | 2,94;373,05 |
I-87 | 2-CF3 | - | H | OCH3 | H | H | 3,14;423,05 |
序号 | (R7)n | (R6)m | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];MSM+H+[m/e]RT[min]);1H-NMR[ppm] |
I-88 | 4-CH2CH3 | - | H | OCH3 | H | H | 3,30;383,15 |
I-89 | 2,3-(CH3)2 | - | H | OCH3 | H | H | 3,22;383,15 |
I-90 | 2,5-(OCH3)2 | - | H | OCH3 | H | H | 2,87;415,05 |
I-91 | 4-N(CH3)2 | - | H | OCH3 | H | H | OI |
I-92 | 2,5-(CH3)2 | - | H | OCH3 | H | H | 3,30;383,15 |
I-93 | 4-OCH3 | - | H | OC2H5 | H | H | 143 |
I-94 | 3-OCF3 | - | H | OCH3 | H | H | 3,19;438,90 |
I-95 | 3-CF3 | - | H | OCH3 | H | H | 3,16;422,90 |
I-96 | 3-F,4-OCH3 | - | H | OCH3 | H | H | 2,78;403,00 |
I-97 | 2-OCH3,5-F | - | H | OCH3 | H | H | 2,91;403,95 |
I-98 | 3-CH3,4-F | - | H | OCH3 | H | H | 3,11;386,95 |
I-99 | 4-OCH2CH3 | - | H | OCH3 | H | H | 3,05;399,05 |
I-100 | 3-Br | - | H | OCH3 | H | H | 3,18;434,85 |
I-101 | 3,4-F2 | - | H | OCH3 | H | H | 2,99;390,95 |
I-102 | 3,4-Cl2 | - | H | OCH3 | H | H | 3,38;422,85 |
I-103 | 3-OCH2CH3 | - | H | OCH3 | H | H | 3,12;399,00 |
I-104 | 2,5-Cl2 | - | H | OCH3 | H | H | 3,27;422,90 |
I-105 | 2,4-(OCH3)2 | - | H | OCH3 | H | H | 2,85;415,05 |
I-106 | 3-OCH3 | - | H | OCH3 | H | H | 2,83;384,95 |
I-107 | 3,5-Br2 | - | H | OCH3 | H | H | 3,55;512,85 |
I-108 | 2-OCH3,5-Cl | - | H | OCH3 | H | H | 3,12;418,95 |
I-109 | 2-F,4-Cl,5-CH3 | - | H | OCH3 | H | H | 3,54;420,95 |
I-110 | 2-CH3,4-F | - | H | OCH3 | H | H | 3,18;387,25 |
I-111 | 4-C(CH3)3 | - | H | OCH3 | H | H | 3,70;411,05 |
序号 | (R7)n | (R6)m | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];MSM+H+[m/e]RT[min]);1H-NMR[ppm] |
I-112 | 3,4-(-OCH2O-) | - | H | OCH3 | H | H | 2,77;398,95 |
I-113 | 4-SCH2CH3 | - | H | OCH3 | H | H | 3,30;414,95 |
I-114 | 2-F,4-Cl | - | H | OCH3 | H | H | 2,97;406,9 |
I-115 | 2-F,4-CH3 | - | H | OCH3 | H | H | 3,02;386,90 |
I-116 | 3,4-(-OCH2CH2O-) | - | H | OCH3 | H | H | 115-119 |
I-117 | 4-F | - | CF3 | H | H | H | 130-132 |
I-118 | 4-CN | - | CF3 | H | H | H | 83-85 |
I-119 | 4-Cl | - | CF3 | H | H | H | 149-151 |
I-120 | 4-F | - | CH3 | H | H | H | 135-140 |
I-121 | 4-Cl | - | CH3 | H | H | H | 168-172 |
I-122 | 4-CN | - | CH3 | H | H | H | 183-186 |
I-123 | 2,4-Cl2 | - | CF3 | H | H | H | 1H-NMR(400MHz in d6-DMSO):δ=8.8(s,1H),8.7(m,1H),8.6(br.,s,1H),7.9-7.8(m,3H),7.6-7.4(m,4H),7.4(m,1H),4.3(s,2H) |
I-124 | 2,4-Cl2 | - | H | Cl | H | H | 1H-NMR(400MHz in d6-DMSO):δ=8.2(m,1H),7.8(m,2H),7.6-7.5(m,3H),7.5-7.4(m,3H),7.2(m,1H),7.1(m,1H),4.2(s,2H) |
序号 | (R7)n | (R6)m | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];MSM+H+[m/e]RT[min]);1H-NMR[ppm] |
I-125 | 2-CF3,4-CF3 | - | CH3 | CH3 | H | H | 161-162℃;1H-NMR(400MHzin d8-THF):δ=8.2(m,2H),8.1(m,1H),7.9(m,2H),7.6(m,1H),7.5(m,2H),7.1(t,1H),6.9(m,1H),4.2(t,2H),2.4(s,3H),2.2(s,3H) |
I-126 | 2,4-Cl2 | - | CH3 | CH3 | H | H | 172-173℃;1H-NMR(400MHzin d8-THF):δ=8.2(m,1H),7.9(m,2H),7.6(m,3H),7.5-7.4(m,2H),7.1(t,1H),6.9(m,1H),4.1(t,2H),2.4(s,3H),2.2(s,3H) |
I-127 | 2-CF3,4-CF3 | - | OCH3 | H | H | H | 124℃ |
对有害真菌的作用实施例
式I化合物的杀真菌作用由下列试验证实:
将活性化合物在丙酮或DMSO中单独或一起配制成含有0.25重量%活性化合物的储备溶液。将1重量%乳化剂UniperolEL(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)加入该溶液中并用水稀释至所需浓度。
走向应用实施例1:对由早疫链格孢引起的西红柿早疫病的活性
将栽培品种为“Golden Queen”的盆栽植物的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将叶子用早疫链格孢在2%生物麦芽溶液中的含水孢子悬浮液侵染,该悬浮液具有0.17×106个孢子/mL的密度。然后将植物置于温度为20-22℃的水蒸气饱和室中。5天后,在未处理但侵染的对照植物上的病害已经发展到可以目测侵染百分数的程度。
在该试验中,用250ppm化合物I-5、I-6、I-8、I-9、I-10、I-12、I-15、I-16、I-24、I-45、I-56、I-61、I-63、I-64、I-65或I-68处理的植物显示出不超过20%的侵染,而未处理植物90%被侵染。
应用实施例2:对由致病疫霉引起的西红柿晚疫病的活性,保护性处理
将盆栽西红柿植物的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将叶子用致病疫霉的含水孢子囊悬浮液侵染。然后将植物置于温度为18-20℃的水蒸气饱和室中。6天后,未处理但侵染的对照植物上的晚疫病发展到可以目测侵染百分数的程度。
在该试验中,用250ppm化合物I-5、I-6、I-8至I-12、I-15、I-16、I-21、I-23、I-24、I-43、I-45、I-46、I-48、I-53、I-54、I-56、I-57、I-58、I-61、I-63至I-68、I-78、I-84、I-87或I-88处理的植物显示出不超过20%的侵染,而未处理植物90%被侵染。
应用实施例3:对隐匿柄锈菌(Puccinia recondita)引起的小麦褐锈病的治疗活性
将栽培品种为“Kanzler”的盆栽小麦秧苗的叶子用褐锈菌(隐匿柄锈菌)的孢子悬浮液接种。然后将盆置于高大气湿度(90-95%)和20-22℃的室中24小时。在此期间,孢子萌发并且芽管穿透到叶组织中。第二天将侵染的植物用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。悬浮液或乳液如上所述制备。在喷雾涂层干燥之后,将试验植物在20-22℃的温度和65-70%的相对大气湿度下在温室中培育7天。然后测定叶子上的锈病真菌发展程度。
在该试验中,用250ppm化合物I-24、I-46、I-47、I-48、I-58、I-63至I-65、I-69或I-87处理的植物显示出不超过20%的侵染,而未处理植物90%被侵染。
式I化合物对有害害虫的作用由下列试验证实:
1.棉蚜(Aphis gossypii),混合生命阶段
将活性化合物在50∶50丙酮/水和100ppm Kinetic表面活性剂中配制。
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。
2.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、植株进食或对幼虫生长的任何干扰。
3.美洲烟叶蛾(烟芽夜蛾(Heliothis virescens))
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。
4.科罗拉多马铃薯甲虫(马铃薯叶甲(Leptinotarsa decemlineata))
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。
5.桃蚜(Myzus persicae)
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天后测定已处理植株上的蚜虫致死率,相对于对照植株上的致死率。
6.银叶粉虱(Bemisia argentifolii)
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。
7.二斑叶螨(二点叶螨(Tetranychus urticae),OP-抗性株)
将活性化合物在50∶50丙酮∶水和100ppm Kinetic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。
8.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。
9.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%AlkamulsEL 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。
10.黄热蚊(埃及伊蚊(Aedes aegypti))
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。
11.黄胸散白蚁(北美散白蚁(Reticulitérmes flávipes))
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。
12.兰花蓟马(Dichromothrips corbetti)
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。
13.通过玻璃接触对阿根廷蚁、收获蚁、举腹蚁(acrobat ant)、木匠蚁、火蚁、家蝇、厩螫蝇、肉蝇、黄热蚊、家蚊、疟蚊、德国小蠊、猫栉头蚤和血红扇头蜱的活性
用0.5mL活性成分的丙酮溶液处理玻璃小瓶(20mL闪光小瓶)。将各小瓶不盖盖子滚动约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℃下并在不同的时间间隔观察处理效果。
14.对墨西哥棉铃象(Anthonomus grandis)的活性
将活性化合物在1∶3二甲亚砜/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,与未处理对照的0%致死率相比,2500ppm下列化合物引起至少75%的致死率:
表36的化合物A-187,表36的化合物A-99,表36的化合物A-363,表25的化合物A-396,表25的化合物A-484,表25的化合物A-670,表1的化合物A-228,表1的化合物A-403,表3的化合物A-516,表3的化合物A-484,表36的化合物A-429,表36的化合物A-396,表36的化合物A-11,表36的化合物A-626,表36的化合物A-55,表36的化合物A-484。
15.对地中海实蝇(Ceratitis capitata)的活性
将活性化合物在1∶3二甲亚砜/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,与未处理对照的0%致死率相比,表1的化合物A-628和表25的化合物A-484在2500ppm下显示出超过75%的致死率。
16.对美洲烟叶蛾(烟芽夜蛾(Heliothis virescens))的活性
将活性化合物在1∶3二甲亚砜/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,与未处理对照的0%致死率相比,2500ppm下列化合物引起至少75%的致死率:
表36的化合物A-187;表36的化合物A-99,表25的化合物A-396;表25的化合物A-484;表25的化合物A-670,表1的化合物A-403,表3的化合物A-516,表36的化合物A-429,表36的化合物A-396,表36的化合物A-11,表36的化合物A-626。
17.对蚕豆修尾蚜(Megoura viciae)的活性
将活性化合物在1∶3二甲亚砜/水中配制。将豆叶盘放入填充有0.8%琼脂和2.5ppm OPUS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。
18.对麦长管蚜(禾谷溢管蚜(Rhopalosiphum padi))的活性
将活性化合物在1∶3二甲亚砜/水中配制。将大麦叶盘放入填充有0.8%琼脂和2.5ppm OPUS的微量滴定板中。用2.5μL试验溶液喷雾叶片并将3-8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5天。基于活的蚜虫评价致死率。试验重复2次。
Claims (22)
1.式I的联苯磺酰胺以及化合物I的N-氧化物、可农用盐和可兽用盐:
其中:
R1为氢、C1-C4烷基、C1-C4烷氧基、C2-C4链烯基、C2-C4炔基或苄基;R2、R3、R4、R5相互独立地为氢、卤素、C1-C4烷基、卤代甲基、C1-C4烷氧基、卤代甲氧基、C1-C4烷硫基、C1-C4烷基氨基或二(C1-C4烷基)氨基;
R6、R7相互独立地为氢、羟基、氰基、硝基、氨基、卤素、C1-C8烷基、C1-C6卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C6烷硫基、(C1-C4烷基)羰基、(C1-C4烷氧基)羰基、-C(R8)=NOR9、(C1-C4烷基)氨基、二(C1-C4烷基)氨基、(C1-C4烷基)氨基羰基、二(C1-C4烷基)氨基羰基、苯基或苯氧基,其中后提到的2个基团中的苯基环可以带有1、2或3个基团R10,
或者
两个基团R6或两个基团R7与它们所连接的苯基环的两个相邻环成员一起可以形成稠合环戊基、环己基或苯基环,其中这些稠合环本身可以带有1或2个基团R10;
m为0、1、2、3或4;
n为0、1、2、3、4或5;
条件是若R2-R5都为氢,则m和n不同时为0;
R8为C1-C4烷基;
R9为C1-C8烷基、C1-C4卤代烷基、C2-C4链烯基、C2-C4卤代链烯基、C2-C4炔基、C2-C4卤代炔基或苄基;
R10为氰基、硝基、卤素、C1-C4烷基、卤代甲基、C1-C4烷氧基或卤代甲氧基。
2.如权利要求1所定义的式I的联苯磺酰胺,其中R1为氢。
3.如权利要求1所定义的式I的联苯磺酰胺,其中R2、R3、R4和R5相互独立地为氢、甲基、乙基、氟、氯、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基或乙硫基。
4.如权利要求1所定义的式I的联苯磺酰胺,其中R2和R5为氢。
5.如权利要求1所定义的式I的联苯磺酰胺,其中R4和R5为氢。
6.如权利要求1所定义的式I的联苯磺酰胺,其中R2、R3、R4和R5为氢。
7.如权利要求1所定义的式I的联苯磺酰胺,其中m为0或1。
8.如权利要求1所定义的式I的联苯磺酰胺,其中R6为卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基。
9.如权利要求1所定义的式I的联苯磺酰胺,其中n为0、1或2且R7为卤素、氰基、硝基、C1-C4烷基、C1-C6卤代烷基、乙酰基、C(CH3)=NOCH3、C1-C8烷氧基、C1-C8卤代烷氧基或C1-C6烷硫基。
10.如权利要求1所定义的式I的联苯磺酰胺,其中n为2、3、4或5。
13.一种适于防治有害真菌的组合物,该组合物包含固体或液体载体和至少一种根据权利要求1的式I的联苯磺酰胺或其N-氧化物或可农用盐。
14.一种处理植物病原性有害真菌的方法,该方法包括用有效量的根据权利要求1的式I的联苯磺酰胺化合物或其N-氧化物或可农用盐处理真菌或需要防止真菌侵袭的材料、植物、土壤或种子。
15.根据权利要求1的式I的联苯磺酰胺、其N-氧化物、可农用盐和可兽用盐以及包含式I化合物的组合物在对抗有害节肢动物中的用途。
16.一种对抗节肢动物门害虫的方法,包括使所述害虫、其栖息地、繁殖地、食物源、节肢动物门害虫生长或可能生长于其中的植物、种子、土壤、区域、材料或环境或需要防止所述害虫侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种根据权利要求1的式I的联苯磺酰胺、其N-氧化物、可农用盐或可兽用盐接触,或与包含至少一种式I的联苯磺酰胺、其N-氧化物、可农用盐或可兽用盐的组合物接触。
17.如权利要求16所要求的方法,其中害虫为昆虫。
18.如权利要求16所要求的方法,其中害虫为蜘蛛纲。
19.一种保护作物以防节肢动物门害虫侵袭或侵染的方法,该方法包括使作物与杀虫有效量的至少一种根据权利要求1的式I的联苯磺酰胺或其N-氧化物或可农用盐接触。
20.一种保护种子以防节肢动物门害虫侵染和保护秧苗的根和芽以防节肢动物门害虫侵染的方法,该方法包括使种子或秧苗的根和芽与杀虫有效量的至少一种根据权利要求1的式I的联苯磺酰胺或其N-氧化物或可农用盐接触。
21.一种保护非活体材料以防节肢动物门害虫侵袭或侵染的方法,该方法包括使非活体材料与杀虫有效量的至少一种根据权利要求1的式I的联苯磺酰胺或其N-氧化物或可农用盐接触。
22.种子,以0.1g-10kg/100kg种子的量包含如权利要求1所定义的式I的联苯磺酰胺或其N-氧化物或可农用盐。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102596908A (zh) * | 2009-12-08 | 2012-07-18 | 贝林格尔.英格海姆国际有限公司 | 用于制备取代的吲唑和氮杂吲唑化合物的中间体的合成方法 |
CN103755601A (zh) * | 2014-01-13 | 2014-04-30 | 河北星宇化工有限公司 | 4,4-双(2-磺酸基苯乙烯基)-1,1-联苯的制备方法 |
CN103755601B (zh) * | 2014-01-13 | 2015-08-12 | 河北星宇化工有限公司 | 4,4-双(2-磺酸基苯乙烯基)-1,1-联苯的制备方法 |
CN113527152A (zh) * | 2021-08-09 | 2021-10-22 | 西北农林科技大学 | 一种联苯磺酰胺类化合物及其防治农作物害虫的方法 |
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