CN100372840C - 用于制备环亚胺的中间体 - Google Patents
用于制备环亚胺的中间体 Download PDFInfo
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- CN100372840C CN100372840C CNB2005100760532A CN200510076053A CN100372840C CN 100372840 C CN100372840 C CN 100372840C CN B2005100760532 A CNB2005100760532 A CN B2005100760532A CN 200510076053 A CN200510076053 A CN 200510076053A CN 100372840 C CN100372840 C CN 100372840C
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- Prior art keywords
- alkyl
- group
- haloalkyl
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- Prior art date
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- 238000002360 preparation method Methods 0.000 title abstract description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 59
- -1 phenyl- Chemical group 0.000 claims description 196
- 150000001875 compounds Chemical class 0.000 claims description 110
- 239000001301 oxygen Substances 0.000 claims description 78
- 229910052760 oxygen Inorganic materials 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 65
- 239000011737 fluorine Substances 0.000 claims description 53
- 229910052731 fluorine Inorganic materials 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 150000002431 hydrogen Chemical class 0.000 claims description 48
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 239000005864 Sulphur Substances 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000001118 alkylidene group Chemical group 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000005504 styryl group Chemical group 0.000 claims description 12
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 3
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 238000000034 method Methods 0.000 description 78
- 239000000203 mixture Substances 0.000 description 74
- 239000002585 base Substances 0.000 description 71
- 238000006243 chemical reaction Methods 0.000 description 51
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 45
- 239000000460 chlorine Substances 0.000 description 45
- 229910052801 chlorine Inorganic materials 0.000 description 45
- 239000002904 solvent Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 33
- 229910052794 bromium Inorganic materials 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000003921 oil Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
- 239000003795 chemical substances by application Substances 0.000 description 27
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 21
- 239000000463 material Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 239000003995 emulsifying agent Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 14
- 150000003851 azoles Chemical class 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 11
- 241000238631 Hexapoda Species 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 241000209094 Oryza Species 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
- 238000003810 ethyl acetate extraction Methods 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- 239000002023 wood Substances 0.000 description 8
- 241001124076 Aphididae Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 241001674048 Phthiraptera Species 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000002541 furyl group Chemical group 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 235000010755 mineral Nutrition 0.000 description 7
- 239000011707 mineral Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000000335 thiazolyl group Chemical group 0.000 description 7
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 6
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000004327 boric acid Substances 0.000 description 6
- 238000001311 chemical methods and process Methods 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012973 diazabicyclooctane Substances 0.000 description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 6
- QDYBCIWLGJMJGO-UHFFFAOYSA-N dinitromethanone Chemical compound [O-][N+](=O)C(=O)[N+]([O-])=O QDYBCIWLGJMJGO-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 230000002147 killing effect Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 5
- 239000005946 Cypermethrin Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 241001259047 Trichodectes Species 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001555 benzenes Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 5
- 229960005424 cypermethrin Drugs 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229940031815 mycocide Drugs 0.000 description 5
- 125000002971 oxazolyl group Chemical group 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- 241000238679 Amblyomma Species 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 241001414720 Cicadellidae Species 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- 241000256054 Culex <genus> Species 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 241000256602 Isoptera Species 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 240000000233 Melia azedarach Species 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 241000238675 Periplaneta americana Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 241001481703 Rhipicephalus <genus> Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001502 aryl halides Chemical class 0.000 description 4
- 210000003323 beak Anatomy 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
- INISTDXBRIBGOC-XMMISQBUSA-N tau-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 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
- 229960002447 thiram Drugs 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 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
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract
本发明涉及用于制备环亚胺的下列通式的中间体。其中Ar1、Ar2代表取代的芳基,n代表1,2或3,m代表1,2,3或4。
Description
本案是优先权申请日为1996年11月20日、中国专利申请号为97181458.9(PCT/EP97/06186)、发明名称为“作为农药的环亚胺”的申请的分案申请。
技术领域
本发明涉及用于制备环亚胺的中间体。
背景技术
先前公开了只有少量取代的环α,α′-二苯基亚胺:三种在2-苯基环上烷氧基取代的2,5-二苯基-1-吡咯啉[Chem.Ber.96,93(1963)中的5-(2,5-二甲氧基苯基)-2-苯基-3,4-二氢-2H-吡咯和5-(4-甲氧基苯基)-2-苯基-3,4-二氢-2H-吡咯和相应的在J.Prakt.Chem.,Series4,1,57(1955)中的4-丙氧基化合物]和没有取代的2,6-二苯基-3,4,5,6-四氢吡啶[参见例如Bull.Soc.Chim.Fr.1974,258,和Chem.Ber.116,3931(1983)]。
对于其作为杀虫剂的用途的适宜性一无所知。
发明内容
因此,本发明提供新的式(I)的环亚胺
其中
n代表1,2或3,
Ar1代表残基
和
Ar2代表残基
其中
m代表0,1,2,3或4,
R1代表卤素,氰基,硝基,烷基,烷氧基,卤代烷基,卤代烷氧基,烷氧基烷基,-S(O)OR6或-NR7R8,
R2和R3各自独立地代表氢,卤素,氰基,硝基,烷基,烷氧基,卤代烷基,卤代烷氧基,烷氧基烷基,-S(O)OR6或-NR7R8,
R4代表卤素,氰基,三烷基甲硅烷基,-CO-NR10R11,四氢吡喃基或者下面基团之一
(1)-X-A
(m)-B-Z-D
(n)-Y E,
R5代表氢,卤素,氰基,硝基,烷基,烷氧基,卤代烷基,卤代烷氧基,烷氧基烷氧基或-S(O)OR6,
o代表0,1或2,
R6代表烷基或卤代烷基,
R7和R8各自独立地代表氢或烷基,或者一起代表亚烷基,
R10和R11各自独立地代表氢,烷基,卤代烷基或者代表苯基或苯基烷基,其各自任选被下面W1所列出的基团一取代或多取代,
X代表直接键,氧,硫,羰基,羰基氧基,氧基羰基,亚烷基,亚烯基,亚炔基,亚烷基氧基,氧基亚烷基,硫基亚烷基,亚烷基二氧基或二烷基亚甲硅基,
A代表苯基,萘基或四氢萘基,其各自任选被下面W1所列出的基团一取代或多取代,或者代表具有一个或多个选自氮,氧和硫的杂原子并且含有一个或2个芳香环的5至10-元杂环基,其任选被下面W2所列出的基团一取代或多取代,
B代表任选被下面W1所列出的基团一取代或二取代的对-亚苯基,
Z代表氧或硫,
D代表氢,烷基,链烯基,炔烃基,卤代烷基,卤代链烯基,各自任选被卤素-,烷基-,链烯基-,卤代链烯基-,苯基-,苯乙烯基-,卤代苯基-或卤代苯乙烯基-取代的环烷基或环烷基烷基,代表各自任选被卤素-或烷基-取代的环烯基或环烯基烷基,代表各自任选被硝基-,卤素-,烷基-,烷氧基-,卤代烷基-或卤代烷氧基-取代的苯基烷基,萘基烷基,四氢萘基烷基或5-或6-元具有1或2个选自氮,氧和硫的杂原子的杂芳基烷基,代表-CO-R12,-CO-NR13R14,或者代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
或者
Z和D一起代表任选被硝基-,卤素-,烷基-,烷氧基-,卤代烷基-或卤代烷氧基-取代的苯氧基烷基,
Y代表直接键,氧,硫,羰基,羰基氧基,氧基羰基,亚烷基,亚烯基,亚炔基,亚烷基氧基,氧基亚烷基,硫代亚烷基,亚烷基二氧基或者代表对亚苯基,其任选被选自W1所列出的基团一取代或二取代,
E代表烷基,链烯基,链炔基,卤代烷基,卤代链烯基,各自任选被卤素-,烷基-,链烯基-,卤代链烯基-,苯基-,苯乙烯基-,卤代苯基-或卤代苯乙烯基-取代的环烷基,代表各自任选被卤素-或烷基-取代的环烯基,代表任选被W1所列出的基团一至四取代的苯基,或者代表具有1或2个选自氮,氧和硫的杂原子并且任选被W2所列出的基团一-至四-取代的5-或6-元杂芳基,或者代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
R12代表烷基,烷氧基,链烯基,链烯基氧基,各自任选被卤素-,烷基-,链烯基-,卤代烷基-或卤代链烯基-取代的环烷基,环烷基氧基或环烷基烷基氧基或者代表各自任选被硝基-,卤素-,烷基-,烷氧基-,卤代烷基-或卤代烷氧基-取代的苯基或萘基,
R13代表氢或烷基,
R14代表烷基,卤代烷基,各自任选被卤素-,烷基-,链烯基-,卤代烷基-或卤代链烯基-取代的环烷基或环烷基烷基或者代表各自任选被卤素-,烷基-,烷氧基-,卤代烷基-或卤代烷氧基-取代的苯基或苯基烷基,
p,q和r各自独立地代表0,1,2或3,其和小于6,
R15和R16各自独立地代表氢或烷基,
G代表氰基,代表各自任选被卤素,烷基或卤代烷基取代的,并且在连接点任选被基团R17取代的,具有1-3个相同或不同的选自氮,氧和硫的杂原子的5-或6-元杂环,或者代表下面的基团之一
(a)-CO-R17
(b)-CO-OR18
(c)-CO-NR19R20
(d)-CS-NR19R20
R17代表氢,烷基,链烯基,卤代烷基,卤代链烯基,任选被卤素-,烷基-或卤代烷基-取代的环烷基,或者代表任选被烷基羰基氨基,烷基羰基烷基氨基和/或选自W3所列出的基团一至五取代的苯基,
R18代表氢,烷基,链烯基,卤代烷基,卤代链烯基,各自任选被卤素-,烷基-,或卤代烷基-取代的环烷基或环烷基烷基或者代表任选被选自W3所列出的基团一至五取代的芳基烷基,
R19和R20各自独立地代表氢,烷基,链烯基,卤代烷基,卤代链烯基,烷氧基,各自任选被卤素-,烷基-或卤代烷基-取代的环烷基或环烷基烷基,代表芳基或芳基烷基,其各自任选被选自W3所列出的基团一至五取代,代表-OR18或-NR17R18或者一起代表其中一个亚甲基任选被氧置换的具有2-6个节的亚烷基链,
R21代表-OR18,-NR17R18或者-N(R17)-COOR18,
R22,R23和R24各自独立地代表烷基,
W1代表氢,卤素,氰基,甲酰基,硝基,烷基,三烷基甲硅烷基,烷氧基,卤代烷基,卤代烷氧基,卤代链烯基氧基,烷基羰基,烷氧羰基,五氟硫基或者-S(O)OR6,
W2代表卤素,氰基,甲酰基,硝基,烷基,三烷基甲硅烷基,烷氧基,卤代烷基,卤代烷氧基,烷基羰基,烷氧羰基,五氟硫基,-S(O)OR6或-C(R17)=N-R21,
W3代表卤素,氰基,硝基,烷基,烷氧基,卤代烷基,卤代烷氧基,二烷基氨基,-S(O)OR6,COOR25或-CONR26R27,
R25代表氢,烷基,卤代烷基,任选被卤素-,烷基-或卤代烷基-取代的环烷基或者代表任选被选自W4所列出的基团一至五取代的苯基,
R26和R27各自独立地代表氢,烷基,链烯基,卤代烷基,卤代链烯基,烷氧基,各自任选被卤素-,烷基-或卤代烷基-取代的环烷基或环烷基烷基,或者代表芳基或芳基烷基,其各自任选被选自W4所列出的基团一至五取代,代表-OR22或-NR23R24或者一起代表其中一个亚甲基任选被氧置换的具有2-6个节的亚烷基链,
W4代表卤素,氰基,硝基,烷基,烷氧基,卤代烷基,卤代烷氧基,二烷基氨基,烷氧基羰基,二烷基氨基羰基或-S(O)OR6。
具体实施方案
式(I)化合物还根据取代基类型可以以几何和/或旋光异构体或者以不同组成的异构体的混合物而存在,如果需要,可以用常规方法拆分异构体混合物。本发明提供纯的异构体还有异构体混合物,其制备和用途以及含有它们的组合物。下面为了简化起见,都是参照式(I)化合物进行,但是既意味着纯的化合物,如果需要,也意味着不同比例异构体化合物的混合物。
此外,发现通过下述方法之一获得式(I)新的化合物。
A)任选在酸结合剂存在下,通过环缩合式(II)的氨基酮或者优选其酸性盐,获得式(I)的环亚胺
其中
Ar1,Ar2和n各自如上定义,
其中
Ar1,Ar2和n各自如上定义。
B)式(I)的环亚胺也可以通过在稀释剂存在下,使式(III)的环O-甲基磺酰基肟与式(IV)的芳基格利雅化合物反应来制备
其中
Ar2和n各自如上定义,
Ar1-Mg-Hal (IV)
其中
Ar1如上定义,
Hal代表氯,溴或碘。
C)式(I-b)的环亚胺
其中
R1,R2,R3,n和m各自如上定义,
R4-1代表A或者下面的基团之一
(m)-B-Z-D
其中
1
A,B,D,E,W1和Z各自如上定义,和
R5-1代表氢,氟,氰基,硝基,烷基,烷氧基,卤代烷基,卤代烷氧基,烷氧基烷氧基或-SR6,其中
R6如上定义,
可以通过在催化剂存在下和在酸结合剂存在下和在溶剂存在下,偶联式(V)的化合物和式(VI)的硼酸来制备
其中
R1,R2,R3,R5-1,n和m各自如上定义,和
X1代表溴,碘或-OSO2CF3
R4-1-B(OH)2(VI)
其中
R4-1如上定义。
D)式(I-c)的环亚胺
R1,R2,R3,R5,n和m各自如上定义,
R4-2代表下面的基团之一
(m-b)-B-Z-D1
(n-b)-Y1-E1
其中
B和Z各自如上定义,
Y1代表氧或硫和
D1和E1各自代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
其中
R15,R16,G,p,q和r各自如上定义,
可以通过缩合式(I-d)的环亚胺和式(VII)的化合物来制备,
R1,R2,R3,R5,n和m各自如上定义,和
R4-3代表下面的基团之一
(m-c)-B-Z-H
(n-c)-Y1-H
其中
B,Y1和Z各自如上定义,
Ab-(CH2)p-(CR15R16)q-(CH2)r-G(VII)
其中
R15,R16,G,p,q和r各自如上定义,
Ab代表离去基团。
E)式(I-e)的环亚胺
其中
R1,R2,R3,R5,n和m各自如上定义,和
R4-4代表选自本发明式(I)化合物的描述中含有基团G的基团,
其中
G代表上述基团(e)至(k)之一,
可以通过相应的酮衍生物,羧酸衍生物或腈,即其中G代表氰基或者基团(a)至(d)之一的式(I)的化合物的常规的和已知的衍生物化作用来制备。
此外发现式(I)的新的化合物作为杀虫剂有好的植物安全性和非常好的活性,特别是在农业中杀节肢动物,而且也杀畜牧业和宠物所遇到的寄生虫。
因此,本发明化合物通过式(I)以一般方式进行了定义。下面详细说明上文和下文所提到的结构式中所列出的基团的优选取代基或范围。
n优选代表1,2或3,
Ar1 优选代表残基
Ar2 优选代表残基
m优选代表0,1,2或3,
R1 优选代表卤素,氰基,硝基,C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷基或C1-C6-卤代烷氧基,代表C1-C6-烷氧基-C1-C6-烷基,-S(O)OR6或-NR7R8,
R2和R3各自独立地优选代表氢,卤素,氰基,硝基,C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷基或C1-C6-卤代烷氧基,代表C1-C6-烷氧基C1-C6-烷基,-S(O)○R6或-NR7R8,
R4 优选代表处于间位或对位的选自卤素,氰基,三-(C1-C6-烷基)-甲硅烷基,-CO-NR10R11,四氢吡喃基或者下面基团之一的取代基
(1)-X-A
(m)-B-Z-D
(n)-Y-E,
R5 优选代表氢,卤素,氰基,硝基,C1-C16-烷基,C1-C16-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C1-C8-烷氧基-C1-C8-烷氧基或-S(O)OR6,
o优选代表0,1或2,
R6 优选代表任选被氟-或氯-取代的C1-C6-烷基,
R7和R8各自独立地优选代表氢或C1-C6-烷基,例如甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基或者一起代表C2-C5-亚烷基,例如-(CH2)4-或-(CH2)5-,
R10和R11各自独立地优选代表氢,C1-C6-烷基,C1-C6-卤代烷基,或者代表苯基或苯基-C1-C4-烷基,其各自任选被下面W1所列出的基团一至三取代,
X优选代表直接键,氧,硫,羰基,羰基氧基,氧基羰基,C1-C4-亚烷基,C2-C4-亚链烯基,C2-C4-亚炔基,C1-C4-亚烷基氧基,C1-C4-氧基亚烷基,C1-C4-硫基亚烷基,C1-C4-亚烷基二氧基或二-C1-C4-烷基亚甲硅基,
A优选代表苯基,萘基或四氢萘基,其各自任选被下面W1所列出的基团一至四取代,或者代表具有1-4个杂原子,包括0-4个氮原子,0-2个氧原子和0-2个硫原子并且含有1个或2个芳香环的5-至10-元杂环基,各种情况下其任选被W2所列出的基团一至四取代(特别是呋喃基,苯并呋喃基,噻吩基,苯并噻吩基,噁唑基,苯并噁唑基,噻唑基,苯并噻唑基,吡咯基,吡啶基,嘧啶基,1,3,5-三嗪基,喹啉基,异喹啉基,吲哚基,嘌呤基,苯并间二氧杂环戊烯基,2,3-二氢化茚基,苯并二噁烷基或苯并二氢吡喃基),
B优选代表任选被W1所列出的基团一取代或二取代的对-亚苯基,
Z优选代表氧或硫,
D优选代表氢,C1-C16-烷基,C2-C16-链烯基,C2-C6-炔基,C1-C16-卤代烷基,C2-C16-卤代链烯基,各自分别任选被卤素-,C1-C4-烷基-,C2-C4-链烯基-,C2-C4-卤代链烯基-,苯基-,苯乙烯基-,卤代苯基-或卤代苯乙烯基-取代的C3-C8-环烷基或C3-C8-环烷基-C1-C6-烷基,代表各自任选被卤素-或C1-C4-烷基-取代的C5-C8-环烯基或C5-C8-环烯基-C1-C4-烷基,代表各自任选被硝基-,卤素-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C6-卤代烷基-或C1-C6-卤代烷氧基-取代的苯基-C1-C6-烷基,萘基-C1-C6-烷基,四氢萘基-C1-C6-烷基或5-或6-元具有1或2个选自氮,氧和硫的杂原子的杂芳基-C1-C6-烷基(特别是呋喃基甲基,噻吩基甲基,吡咯基甲基,噁唑基甲基,异噁唑基甲基,噻唑基甲基或吡啶基甲基),代表-CO-R12,-CO-NR13R14,或者代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
Z和D一起优选代表任选被硝基-,卤素-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C6-卤代烷基-或C1-C6-卤代烷氧基-取代的苯氧基-C1-C4-烷基,
Y优选代表直接键,氧,硫,羰基,羰基氧基,氧基羰基,C1-C4-亚烷基,C2-C4-亚烯基,C2-C4-亚炔基,C1-C4-亚烷基氧基,C1-C4-氧基亚烷基,C1-C4-硫基亚烷基,C1-C4-亚烷基二氧基或者代表对亚苯基,其任选被选自W1所列出的基团一取代或二取代,
E优选代表氢,C1-C16-烷基,C2-C16-链烯基,C2-C6-炔基,C1-C16-卤代烷基,C2-C16-卤代链烯基,任选被卤素-,C1-C4-烷基-,C2-C4-链烯基-,C2-C4-卤代链烯基-,苯基-,苯乙烯基-,卤代苯基-或卤代苯乙烯基-取代的C3-C8-环烷基,代表任选被卤素-或C1-C4-烷基-取代的C5-C8环烯基,代表任选被W1所列出的基团一-至四-取代的苯基,或者代表具有1或2个选自氮,氧和硫的杂原子并且任选被W2所列出的基团一-至四-取代的5-或6-元杂芳基(特别是呋喃基,噻吩基,吡咯基,噁唑基,异噁唑基,噻唑基或吡啶基),或者代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
R12 优选代表C1-C12-烷基,C1-C12-烷氧基,C2-C12-链烯基,C2-C12-链烯基氧基,各自任选被卤素-,C1-C4-烷基-,C2-C4-链烯基-,C1-C4-卤代烷基-或C2-C4-卤代链烯基-取代的C3-C8-环烷基,C3-C8-环烷基氧基或C3-C8-环烷基-C1-C6-烷基氧基或者代表各自任选被硝基-,卤素-,C1-C12-烷基-,C1-C12-烷氧基-,C1-C12-卤代烷基-或C1-C12-卤代烷氧基一至四取代的苯基或萘基,
R13 优选代表氢或C1-C12-烷基,
R14 优选代表C1-C12-烷基,C1-C12-卤代烷基,各自任选被卤素-,C1-C4-烷基-,C2-C4-链烯基-,C1-C4-卤代烷基-或C2-C4-卤代链烯基-取代的C3-C8-环烷基或C3-C8-环烷基-C1-C6-烷基或者代表各种情况下任选被卤素-,C1-C12-烷基-,C1-C12-烷氧基-,C1-C12-卤代烷基-或C1-C12-卤代烷氧基一至四取代的苯基或苯基-C1-C6-烷基,
p,q和r各自独立地优选代表0,1,2或3,其和小于6,
R15和R16各自独立地优选代表氢或C1-C4-烷基,
G优选代表氰基,代表任选被卤素,C1-C4-烷基或C1-C4-卤代烷基一至三取代的,并且在连接点任选被基团R17取代的,具有1-3个相同或不同的选自氮,氧和硫的杂原子的5-或6-元杂环(特别是5,6-二氢二噁嗪-2-基,3-吡啶基,3-呋喃基,3-噻吩基,2-噻唑基,5-噻唑基,2-二氧戊环基,1,3-二氧戊环-2-基,2-二硫戊环基,1,3-二硫戊环-2-基或1,3-噻噁烷-2-基),或者代表下面的基团之一
(a)-CO-R17
(b)-CO-OR18
(c)-CO-NR19R20
(d)-CS-NR19R20
R17 优选代表氢,C1-C6-烷基,C2-C6-链烯基,C1-C4-卤代烷基,C2-C6-卤代链烯基,任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C6-环烷基,或者代表任选被C1-C4-烷基羰基氨基,C1-C4-烷基羰基-C1-C4-烷基氨基和/或选自W3所列出的基团一至五取代的苯基,
R18 优选代表氢,C1-C4-烷基,C2-C6-链烯基,C1-C4-卤代烷基,C2-C6-卤代链烯基,各自任选被卤素-,C1-C4-烷基-或C1-C4-卤
代烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基或者代表任选被选自W3所列出的基团一至四取代的C6-C10-芳基-C1-C4-烷基(特别是苯基-C1-C4-烷基或萘基-C1-C4-烷基),
R19和R20各自独立地优选代表氢,C1-C4-烷基,C3-C6-链烯基,C1-C4-卤代烷基,C3-C6-卤代链烯基,C1-C4-烷氧基,各自任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表苯基或苯基-C1-C4-烷基,其各自任选被选自W3所列出的基团一至五取代,代表-OR18或-NR17R18或者一起代表其中一个亚甲基任选被氧置换的具有4-6个节的亚烷基链,
R21 优选代表-OR18,-NR17R18或者-N(R17)-COOR18,
R22,R23和R24各自独立地优选代表C1-C6-烷基,
W1 优选代表氢,卤素,氰基,甲酰基,硝基,C1-C6-烷基,三-C1-C4-烷基甲硅烷基,C1-C16-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C2-C6-卤代链烯基氧基,C1-C6-烷基羰基,C1-C16-烷氧羰基,五氟硫基或者-S(O)OR6,
W2 优选代表卤素,氰基,甲酰基,硝基,C1-C6-烷基,三-C1-C4-烷基甲硅烷基,C1-C16-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C1-C6-烷基羰基,C1-C16-烷氧羰基,五氟硫基,-S(O)OR6或-C(R17)=N-R21,
W3 优选代表卤素,氰基,硝基,C1-C4-烷基,C1-C4-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,二-C1-C4-烷基氨基,-S(O)OR6,COOR25或-CONR26R27,
R25 优选代表氢,C1-C4-烷基,C1-C4-卤代烷基,任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C7-环烷基或者代表任选被选自W4所列出的基团一至五取代的苯基,
R26和R27各自独立地优选代表氢,C1-C4-烷基,C3-C6-链烯基,C1-C4-卤代烷基,C3-C6-卤代链烯基,C1-C4-烷氧基,各自任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,或者代表苯基或苯基-C1-C4-烷基,其各自任选被选自W4所列出的基团一至五取代,代表-OR22或-NR23R24或者一起代表其中一个亚甲基任选被氧置换的具有4-6个节的亚烷基链,
W4 优选代表卤素,氰基,硝基,C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,二-C1-C4-烷基氨基,C1-C6-烷氧基羰基,二-C1-C6-烷基氨基羰基或-S(O)OR6。
n特别优选代表1或2,
Ar1 特别优选代表残基
Ar2 特别优选代表残基
m特别优选代表0,1或2,
R1 特别优选代表氟,氯,溴,C1-C6-烷基,C1-C6-烷氧基,分别被氟-或氯-取代的C1-C6-烷基或C1-C6-烷氧基,代表C1-C6-烷氧基-C1-C6-烷基或-S(O)OR6,
R2和R3各自独立地特别优选代表氢,氟,氯,溴,碘,C1-C6-烷基,C1-C6-烷氧基,分别被氟-或氯-取代的C1-C6-烷基或C1-C6-烷氧基,代表C1-C6-烷氧基-C1-C6-烷基或-S(O)OR6
R4 特别优选代表处于间位或对位的选自氟,氯,溴,碘,氰基,三-(C1-C4-烷基)-甲硅烷基,-CO-NR10R11,四氢吡喃基或者下面基团之一的取代基
(1)-X-A
(m)-B-Z-D
(n)-Y-E,
R5 特别优选代表氢,氟,氯,溴,碘,氰基,硝基,C1-C16-烷基,C1-C16-烷氧基,分别被氟-或氯-取代的C1-C6-烷基或C1-C6-烷氧基,代表C1-C8-烷氧基-C1-C8-烷氧基或-S(O)OR6,
o特别优选代表0,1或2,
R6 特别优选代表C1-C4-烷基或任选被氟-或氯-取代的甲基或乙基,
R10和R11各自独立地特别优选代表氢,C1-C6-烷基,氟-或氯-取代的C1-C6-烷基或者代表苯基或苄基,其各自任选被W1所列出的基团一或二取代,
X特别优选代表直接键,氧,硫,羰基,羰基氧基,氧基羰基,C1-C4-亚烷基,C2-C4-亚链烯基,C2-C4-亚炔烃基,C1-C4-亚烷基氧基,C1-C4-氧基亚烷基,C1-C4-硫基亚烷基,C1-C4-亚烷基二氧基或二-C1-C4-烷基亚甲硅基,
A特别优选代表苯基,萘基或四氢萘基,其各自任选被W1所列出的基团一至三取代,或者代表具有1-4个杂原子,包括0-4个氮原子,0-2个氧原子和0-2个硫原子并且含有1个或2个芳香环的5-至10-元杂环基,各种情况下其任选被W2所列出的基团一至三取代(特别是呋喃基,苯并呋喃基,噻吩基,苯并噻吩基,噁唑基,苯并噁唑基,噻唑基,苯并噻唑基,吡咯基,吡啶基,嘧啶基,1,3,5-三嗪基,喹啉基,异喹啉基,吲哚基,嘌呤基,苯并间二氧杂环戊烯基,2,3-二氢化茚基,苯并二噁烷基或苯并二氢吡喃基),
B特别优选代表任选被W1所列出的基团一取代或二取代的对-亚苯基,
Z特别优选代表氧或硫,
D特别优选代表氢,C1-C16-烷基,C2-C16-链烯基,C2-C6-炔基,分别被氟-或氯-取代的C1-C4-烷基或C2-C4-链烯基,代表各自任选被氟-,氯-,溴-,C1-C4-烷基-,C2-C4-链烯基-,氟-或氯-取代的C2-C4-链烯基,被苯基、苯乙烯基、各自任选被氟、氯或溴取代的苯基或苯乙烯基取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表各自任选被氟-,氯-,溴-或C1-C4-烷基-取代的C5-C6-环烯基或C5-C6-环烯基-C1-C4-烷基,代表苯基-C1-C4-烷基,萘基-C1-C4-烷基,四氢萘基-C1-C6-烷基或5-或6-元具有1或2个选自氮,氧和硫的杂原子的杂芳基-C1-C4-烷基(特别是呋喃基甲基,噻吩基甲基,吡咯基甲基,噁唑基甲基,异噁唑基甲基,噻唑基甲基或吡啶基甲基),这些取代基各自任选被硝基,氟,氯,溴,C1-C6-烷基,C1-C6-烷氧基,各自被氟-或氯-取代的C1-C4-烷基或C1-C4-烷氧基取代,代表-CO-R12,-CO-NR13R14,或者基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
Z和D还一起特别优选代表任选被硝基,氟,氯,溴,C1-C4-烷基-,C1-C4-烷氧基-,或者各自被氟-或氯-取代的C1-C4-烷基-或C1-C4-烷氧基-取代的苯氧基-C1-C3-烷基,
Y特别优选代表直接键,氧,硫,羰基,羰基氧基,氧基羰基,C1-C4-亚烷基,C2-C4-亚烯基,C2-C4-亚炔基,C1-C4-亚烷基氧基,C1-C4-氧基亚烷基,C1-C4-硫基亚烷基,C1-C4-亚烷基二氧基或者代表对-亚苯基,其任选被选自W1所列出的基团一取代或二取代,
E特别优选代表氢,C1-C16-烷基,C2-C16-链烯基,C2-C6-炔基,分别被氟-或氯-取代的C1-C4-烷基或C2-C4-链烯基,代表任选被氟,氯,溴,C1-C4-烷基,C2-C4-链烯基,氟-或氯-取代的C2-C4-链烯基,苯基,苯乙烯基或者分别被氟-,氯-或溴-取代的苯基-或苯乙烯基取代的C3-C6-环烷基,代表任选被氟-,氯-,溴-或C1-C4-烷基-取代的C5-C6环烯基,代表任选被W1所列出的基团一或二取代的苯基,或者代表具有1或2个选自氮,氧和硫的杂原子并且任选被W2所列出的基团一或二取代的5-或6-元杂芳基(特别是呋喃基,噻吩基,吡咯基,噁唑基,异噁唑基,噻唑基或吡啶基),或者代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
R12 特别优选代表C1-C6-烷基,C1-C6-烷氧基,C2-C6-链烯基,C2-C6-链烯基氧基,代表各自任选被氟,氯,C1-C3-烷基或者各自被氟-或氯-取代的C1-C2-烷基-或C2-C3-链烯基-取代的C3-C6-环烷基,C3-C6-环烷基氧基或C3-C6-环烷基-C1-C2-烷基氧基,或者代表任选被氟,氯,溴,碘,C1-C4-烷基-,C1-C4-烷氧基-或者分别被氟-或氯-取代的C1-C3-烷基或C1-C4-烷氧基一或二取代的苯基,
R13 特别优选代表氢或C1-C4-烷基,
R14 特别优选代表C1-C4-烷基,或者代表各自任选被氟,氯,溴,C1-C4-烷基,或者各自被氟-或氯-取代的C1-C4-烷基或C1-C4-烷氧基一或二取代的苯基或苄基,
p,q和r各自独立地特别优选代表0,1,2或3,其和小于6,
R15和R16各自独立地特别优选代表氢或C1-C4-烷基,
G特别优选代表氰基,代表任选被氟,氯,溴,C1-C4-烷基或被氟-或氯-取代的C1-C4-烷基一至三取代的,并且在连接点任选被基团R17取代的,具有1-3个相同或不同的选自氮,氧和硫的杂原子的5-或6-元杂环(特别是5,6-二氢二噁嗪-2-基,3-吡啶基,3-呋喃基,3-噻吩基,2-噻唑基,5-噻唑基,2-二氧戊环基,1,3-二氧戊环-2-基,2-二硫戊环基,1,3-二硫戊环-2-基或1,3-噻噁烷-2-基),或者代表下面的基团之一
(a)-CO-R17
(b)-CO-OR18
(c)-CO-NR19R20
(d)-CS-NR19R20
R17 特别优选代表氢,C1-C6-烷基,C2-C6-链烯基,分别被氟-或氯-取代的C1-C4-烷基或C2-C6-链烯基,代表任选被氟,氯,C1-C4-烷基或氟-或氯-取代的C1-C4-烷基-取代的C3-C6-环烷基,或者代表任选被C1-C4-烷基羰基氨基,C1-C4-烷基羰基-C1-C4-烷基氨基和/或选自W3所列出的基团一至三取代的苯基,
R18 特别优选代表氢,C1-C4-烷基,C3-C6-链烯基,分别被氟-或氯-取代的C1-C4-烷基或C3-C6-链烯基,代表各自任选被氟,氯,C1-C4-烷基或氟-或氯-取代的C1-C4-烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,或者代表各自任选被选自W3所列出的基团一至三取代的苯基-C1-C4-烷基或萘基-C1-C4-烷基,
R19和R20各自独立地特别优选代表氢,C1-C4-烷基,C3-C6-链烯基,分别被氟-或氯-取代的C1-C4-烷基或C3-C6-链烯基,代表C1-C4-烷氧基,代表各自任选被氟,氯,C1-C4-烷基或氟-或氯-取代的C1-C4-烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表苯基或苯基-C1-C4-烷基,其各自任选被选自W3所列出的基团一至三取代,代表-OR18或-NR17R18或者一起代表-(CH2)5-,-(CH2)6-或-(CH2)2-O-(CH2)2-
R21 特别优选代表-OR18,-NR17R18或者-N(R17)-COOR18,R22,R23和R24各自独立地特别优选代表C1-C4-烷基,W1 特别优选代表氢,氟,氯,溴,碘,氰基,甲酰基,硝基,C1-C4-烷基,C1-C4-烷氧基,分别被氟-或氯-取代的C1-C4-烷基或C1-C4-烷氧基,代表C1-C4-烷基羰基,C1-C4-烷氧羰基或者-S(O)OR6,
W2 特别优选代表氟,氯,溴,氰基,甲酰基,硝基,C1-C4-烷基,C1-C4-烷氧基,分别被氟-或氯-取代的C1-C4-烷基或C1-C4-烷氧基,代表C1-C4-烷基羰基,C1-C4-烷氧羰基,-S(O)OR6或-C(R17)=N-R21,
W3 特别优选代表氟,氯,溴,氰基,硝基,C1-C4-烷基,C1-C4-烷氧基,分别被氟-或氯-取代的C1-C4-烷基或C1-C4-烷氧基,代表二-C1-C4-烷基氨基,-S(O)OR6,COOR25或-CONR26R27,
R25 特别优选代表氢,C1-C4-烷基,氟-或氯-取代的C1-C4-烷基,代表任选被氟,氯,C1-C4-烷基-或氟-或氯-取代的C1-C4-烷基-取代的C3-C6-环烷基或者代表任选被选自W4所列出的基团一至三取代的苯基,
R26和R27各自独立地特别优选代表氢,C1-C4-烷基,C3-C6-链烯基,分别被氟-或氯-取代的C1-C4-烷基或C3-C6-链烯基,代表C1-C4-烷氧基,代表各自任选被氟,氯,C1-C4-烷基或被氟-或氯-取代的C1-C4-烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,或者代表苯基或苯基-C1-C4-烷基,其各自任选被选自W4所列出的基团一至三取代,代表-OR22或-NR23R24或者一起代表-(CH2)5-,-(CH2)6-或-(CH2)2-O-(CH2)2-,
W4 特别优选代表氟,氯,溴,氰基,硝基,C1-C4-烷基,C1-C4-烷氧基,分别被氟-或氯-取代的C1-C4-烷基或C1-C4-烷氧基,二-C1-C4-烷基氨基,C1-C4-烷氧基羰基,二-C1-C6-烷基氨基羰基或-S(O)OR6。
n非常特别优选代表1或2,特别代表1,
Ar1 非常特别优选代表残基
Ar2 非常特别优选代表残基
R1 非常特别优选代表氟,氯,溴,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基,
R2和R3各自独立地非常特别优选代表氢,氟,氯,溴,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基,
R4 非常特别优选代表处于间位或对位的选自氟,氯,溴,碘,氰基,-CO-NR10R11,四氢吡喃基或者下面基团之一的取代基
(1)-X-A
(n)-Y-E,
R5 非常特别优选代表氢,氟,氯,溴,甲基,乙基,甲氧基,乙氧基,甲硫基,乙硫基,三氟甲基,二氟甲氧基,三氟甲氧基或三氟甲硫基,
o非常特别优选代表0或2,
R6 非常特别优选代表甲基,乙基,正丙基,异丙基,二氟甲基或三氟甲基,
R10和R11各自独立地非常特别优选代表氢,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,或者代表苯基或苄基,其各自任选被W1所列出的基团一取代,
X非常特别优选代表直接键,氧,硫,羰基,-CH2-,-(CH2)2-,-CH=CH-,(E或Z),-C≡C-,-CH2O-,-(CH2)2O-,-CH(CH3)O-,-OCH2-,-O(CH2)2-,-SCH2-,-S(CH2)2-,-SCH(CH3)-,C1-C4-亚烷基二氧基,特别是-OCH2O-,-O(CH2)2O-或-OCH(CH3)O-,
A非常特别优选代表苯基,其任选被W1所列出的基团一或二取代,或者代表呋喃基,苯并呋喃基,噻吩基,苯并噻吩基,噁唑基,苯并噁唑基,噻唑基,苯并噻唑基,吡咯基,吡啶基,嘧啶基,1,3,5-三嗪基,喹啉基,异喹啉基,吲哚基,嘌呤基,苯并间二氧杂环戊烯基,2,3-二氢化茚基,苯并二噁烷基或苯并二氢吡喃基,其各自任选被W2所列出的基团一或二取代,
Z非常特别优选代表氧或硫,
D非常特别优选代表氢,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,异构体戊基,异构体己基,正庚基,正辛基,异辛基,正壬基,正癸烷基,正十一烷基,正十二烷基,正十三烷基,正十四烷基,正十五烷基,正十六烷基,2-丙烯基,丁烯基,戊烯基,己烯基,丙炔基,丁炔基,戊炔基,-CF3,-CHF2,-CClF2,-CF2CHFCl,-CF2CH2F,-CF2CHF2,-CF2CCl3,-CH2CF3,-CF2CHFCF3,-CH2CF2CHF2,-CH2CF2CF3,代表各自任选被氟,氯,溴,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,乙烯基,1-丙烯基,2,2-二甲基乙烯基,-CH=CCl2,苯基,苯乙烯基,分别被氟-,氯-或溴-取代的苯基或4-氯苯乙烯基一至三取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,代表各自任选被氟-,氯-,甲基-,乙基-,正丙基-,异丙基-,正丁基-,异丁基-,仲丁基-或叔丁基-取代的环戊烯基,环己烯基,环己烯基甲基或环戊烯基甲基,代表苄基,苯乙基,萘基甲基,四氢萘基甲基,呋喃基甲基,噻吩基甲基,吡咯基甲基,噁唑基甲基,异噁唑基甲基,噻唑基甲基或吡啶基甲基,其各自任选被硝基,氟,氯,溴,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基,三氟甲基,三氟甲氧基,二氟甲氧基或氯代二氟甲氧基取代,代表-CO-R12,-CO-NR13R14,或者基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
Z和D还一起非常特别优选代表任选被硝基,氟,氯,溴,甲基,乙基,正丙基,异丙基,甲氧基,乙氧基,正丙氧基,异丙氧基,三氟甲基,三氟甲氧基,二氟甲氧基或氯代二氟甲氧基一或二取代的苯氧基甲基,
Y非常特别优选代表直接键,氧,硫,羰基,-CH2-,-(CH2)2-,-CH=CH-,(E或Z),-C≡C-,-CH2O-,-(CH2)2O-,-CH(CH3)O-,-OCH2-,-O(CH2)2-,-SCH2-,-S(CH2)2-,-SCH(CH3)-,C1-C4-亚烷基二氧基,特别是-OCH2O-或-O(CH2)2O-,
或者代表对-亚苯基,其任选被选自W1所列出的基团一取代,
E非常特别优选代表氢,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,异构体戊基,异构体己基,正庚基,正辛基,异辛基,正壬基,正癸烷基,正十一烷基,正十二烷基,正十三烷基,正十四烷基,正十五烷基,正十六烷基,2-丙烯基,丁烯基,戊烯基,己烯基,丙炔基,丁炔基,戊炔基,-CF3,-CHF2,-CClF2,-CF2CHFCl,-CF2CH2F,-CF2CHF2,-CF2CCl3,-CH2CF3,-CF2CHFCF3,-CH2CF2CHF2,-CH2CF2CF3,代表各自任选被氟,氯,溴,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,乙烯基,1-丙烯基,2,2-二甲基乙烯基,-CH=CCl2,苯基,苯乙烯基,分别被氟-,氯-或溴-取代的苯基或4-氯苯乙烯基一至三取代的环丙基,环丁基,环戊基或环己基,代表各自任选被氟-,氯-,甲基-,乙基-,正丙基-,异丙基-,正丁基-,异丁基-,仲丁基-或叔丁基-取代的环戊烯基或环己烯基,代表任选被W1所列出的基团一-或二取代的苯基,代表呋喃基,噻吩基,吡咯基,噁唑基,异噁唑基,噻唑基或吡啶基,其各自任选被W2所列出的基团一或二取代,或者代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
R12 非常特别优选代表甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基,环丙基,环己基,环己基氧基,环己基甲基氧基,苯基,2-氯苯基,3-氯苯基,2,6-二氟苯基,2,4-二氯苯基,3,4-二氯苯基,2-三氟甲氧基苯基或4-三氟甲氧基苯基,
R13 非常特别优选代表氢,
R14 非常特别优选代表甲基,乙基或者代表任选被氯一取代的苯基,
p,q和r各自独立地非常特别优选代表0,1,2或3,其和小于4,
R15和R16各自独立地非常特别优选代表氢,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,
G非常特别优选代表氰基,代表5,6-二氢二噁嗪-2-基,3-吡啶基,3-呋喃基,3-噻吩基,2-噻唑基,5-噻唑基,2-二氧戊环基,1,3-二氧戊环-2-基,2-二硫戊环基,1,3-二硫戊环-2-基或1,3-噻噁烷-2-基,其各自任选被氟,氯,溴,甲基,乙基,正丙基,异丙基或三氟甲基取代,并且在连接点,任选被R17取代,或者代表下面的基团之一
(a)-CO-R17
(b)-CO-OR18
(c)-CO+NR19R20
(d)-CS-NR19R20
R17 非常特别优选代表氢,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,异构体戊基,异构体己基,-CF3,-CHF2,-CClF2,-CF2CHFCl,-CF2CH2F,-CF2CHF2,-CF2CCl3,-CH2CF3,C3-C6-链烯基,被氟或氯一至三取代的C3-C6-链烯基,代表各自任选被氟,氯,甲基,乙基,正丙基,异丙基,-CF3,-CHF2,-CClF2,-CF2CHFCl,-CF2CH2F,-CF2CHF2,-CF2CCl3或-CH2CF3一或二取代的环丙基,环戊基或环己基,或者代表任选被甲基羰基氨基,乙基羰基氨基,甲基羰基-甲基氨基和/或W3所列出的基团一-或二取代的苯基,
R18 非常特别优选代表氢,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,-CH2F3,烯丙基,代表各自任选被氟,氯,甲基,乙基,正丙基,异丙基,-CF3,-CHF2,-CClF2,-CF2CHFCl,-CF2CH2F,-CF2CHF2,-CF2CCl3或-CH2CF3一-或二取代的环丙基,环戊基,环己基,环丙基甲基,环戊基甲基,环己基甲基,环丙基乙基,环戊基乙基或环己基乙基,或者代表任选被W3所列基团一-或二取代的苄基或苯乙基,
R19和R20各自独立地非常特别优选代表氢,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,-CH2CF3,甲氧基,乙氧基,烯丙基,代表各自任选被氟,氯,甲基,乙基,正丙基,异丙基,或三氟甲基一或二取代的环丙基,环戊基,环己基,环丙基甲基,环戊基甲基或环己基甲基,代表苯基,苄基或苯乙基,其各自任选被选自W3所列出的基团一-或二取代,代表-OR18或-NR17R18,
R21 非常特别优选代表-OR18,-NR17R18或者-N(R17)-COOR18,
R22,R23和R24各自独立地非常特别优选代表甲基,乙基,正丙基或异丙基,
W1 非常特别优选代表氢,氟,氯,溴,氰基,甲酰基,硝基,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,异丁氧基,仲丁氧基,叔丁氧基,-CF3,-CHF2,-CClF2,-CF2CHFCl,-CF2CH2F,-CF2CHF2,-CF2CCl3,-CH2CF3,-CF2CHFCF3,-CH2CF2CHF2,-CH2CF2CF3,三氟甲氧基,二氟甲氧基,氯代二氟甲氧基,乙酰基,丙酰基,丁酰基,异丁酰基,甲氧羰基,乙氧羰基,正丙氧羰基,异丙氧羰基,正丁氧羰基,异丁氧羰基,仲丁氧羰基,叔丁氧羰基或者-S(O)OR6,
W2 非常特别优选代表氟,氯,溴,氰基,甲基,乙基,正丙基,异丙基,三氟甲基,三氟甲氧基,二氟甲氧基,氯代二氟甲氧基,乙酰基,三氟甲硫基,-CH=N-OCH3,-CH=N-OC2H5,-CH=N-OC3H7,-C(CH3)=N-OCH3,-C(CH3)=N-OC2H5,-C(CH3)=N-OC3H7,-C(C2H5)=N-OCH3,-C(C2H5)=N-OC2H5或-C(C2H5)=N-OC3H7,
W3 非常特别优选代表氟,氯,氰基,硝基,甲基,乙基,甲氧基,乙氧基,甲硫基,三氟甲基,三氟甲氧基,三氟甲硫基,二甲基氨基,二乙基氨基,-COOR25或-CONR26R27,
R25 非常特别优选代表氢,甲基,乙基,正丙基,异丙基,叔丁基,-CH2CF3,代表各自任选被氟,氯,甲基,乙基,正丙基,异丙基或-CF3一或二取代的环丙基,环戊基或环己基,或者代表任选被选自W4所列出的基团一或二取代的苯基,
R26和R27各自独立地非常特别优选代表氢,甲基,乙基,正丙基,异丙基,正丁基,异丁基,仲丁基,叔丁基,-CH2CF3,甲氧基,乙氧基,烯丙基,代表各自任选被氟或氯一或二取代的环丙基,环戊基,环己基,环丙基甲基,环戊基甲基或环己基甲基,代表苯基,苄基或苯乙基,其各自任选被选自W4所列出的基团一或二取代,代表-OR22或-NR23R24,
W4 非常特别优选代表氟,氯,溴,氰基,硝基,甲基,乙基,叔丁基,甲氧基,乙氧基,甲硫基,三氟甲基,三氟甲氧基或三氟甲硫基。
此外,给出了优选的式(I-a)化合物
其中
R1,R2,R3,R5和n各自具有上述一般的,优选的,特别优选的或者非常特别优选的定义,
R4代表被W1所列出的基团一或二取代的苯基或者下面的基团之
(m-b)-B-O-D
(1)-Y-E,
B代表任选被W1所列出的基团一取代的对-亚苯基,
Y代表直接键或者代表任选被W1所列出的基团一或二取代的对-亚苯基,
D和E各自具有上述非常特别优选的定义,其中
G代表氰基或者下面的基团之一
(a)-CO-R17
其中
R17和R21各自具有上述一般的,优选的,特别优选的或者非常特别优选的定义,和
W1具有上述一般的,优选的,特别优选的或者非常特别优选的定义。
此外,给出了优选的式(I-f)化合物
其中
R1代表卤素,特别是氟或氯,尤其是氟,
R2代表卤素,特别是氟或氯,尤其是氟,和
R4代表a)被选自W2的基团一或二取代的苯基或者
b)被选自W2的基团一或二取代的杂芳基(特别是呋喃基,噻吩基,吡咯基,噁唑基,异噁唑基,噻唑基或吡啶基,尤其是噻吩基)。
上述基团的一般或优选定义或详细说明可以根据需要相互结合,也就是说各范围和优选范围之间的任意组合也是可能的。定义适用于终产物和相应地适用于母体和中间体。
本发明优选包含上述给定的作为优选(优选地)的定义的组合的式(I)化合物。
本发明特别优选包含上述给定的作为特别优选的定义的组合的式(I)化合物。
本发明非常特别优选包含上述给定的作为非常特别优选的定义的组合的式(I)化合物。
饱和的或不饱和的烃基例如烷基或链烯基--还有与杂原子的连接,例如在烷氧基中--在各种情况下,只要有可能,可以是直链或支链的。
任选被取代的基团可以是一取代或多取代的,多取代情况下的取代基可以是相同或不同的。如果几个取代基具有相同的指数,例如在m>1情况下m个基团R5,这些基团可以是相同或不同的。
如果例如使用三氟乙酸[1-(4-乙基-2-甲基-苯基)-5-(2-甲基苯甲酰基)-1-戊基]-铵为起始物,则本发明方法(A)的反应过程可以通过下面的反应式详细说明:
如果例如使用2-(4-甲氧基苯基)-环戊酮O-甲磺酰基肟和2-甲苯基溴化镁为起始物,则本发明方法(B)的反应过程可以通过下面的反应式详细说明:
如果例如使用2-(2-甲基苯基)-5-(4-碘代苯基)-3,4-二氢-2H-吡咯和4-氰基甲氧基苯基硼酸为起始物,则本发明方法(C)的反应过程可以通过下面的反应式详细说明:
如果例如使用2-(2-溴-4-氟-6-甲基-苯基)-5-(3′-氯-4′-羟基联苯基-4-基)-3,4-二氢-2H-吡咯和α-溴代戊酸甲酯为起始物,则本发明方法(D)的反应过程可以通过下面的反应式详细说明:
如果例如使用6-(4’-环丙基羰基甲氧基-3-三氟甲氧基-联苯基-4-基)-2-(2-甲基苯基)-3,4,5,6-四氢吡啶和O-甲基羟基胺为起始物,则本发明方法(E)的反应过程可以通过下面的反应式详细说明:
进行本发明方法(A)所需要的氨基酮通过式(II)以一般方式定义。在该结构式中,Ar1,Ar2和n各自优选具有已经提到的与描述式(I)的环亚胺相关的作为优选的那些定义。式(II)的氨基酮是新的。
式(II)的氨基酮可以例如在根据下面的反应式的方法(A.a)中通过除去式(VIII)的氨基酮衍生物的BOC(叔-丁氧羰基)保护基来制备,式(VIII)也是新的:
如果需要,该反应可以在溶剂例如二氯甲烷存在下,通过利用去除叔-丁氧羰基氨基保护基的常规方法,优选通过使用三氟乙酸酸解来进行(参见,例如T.W.Greene,P.G.M.Wuts,有机合成中的保护基团(Protective Groups in Organic Synthesis),第二版,John Wiley&Sons,纽约1991)。这里,式(II)的氨基酮优选分离为有机或无机布朗斯特酸的盐,所述酸是例如氢氟酸,盐酸,硫酸,磷酸,甲酸,乙酸,苯甲酸,柠檬酸,三氟乙酸,甲磺酸,三氟甲磺酸或甲苯磺酸。
式(VIII)的氨基酮衍生物可以例如根据下面的反应式,在0℃和80℃之间的温度下使式(IX)的BOC-保护的内酰胺与式(X)的金属化芳烃反应来制备:
在式(X)中,Met代表一价金属残基,例如Li,MgI,MgBr或MgCl。
一些式(X)的金属化芳烃是已知的或者其可以通过已知的方法,例如lithiation或格利雅反应,从相应的芳烃或卤代芳烃制备。
式(IX)的保护的内酰胺例如通过式(XI)的BOC-保护的内酰胺,通过常规方法,例如用丁基锂金属化和与碳酸氢二叔丁酯反应而获得(参见,例如T.W.Greene,P.G.M.Wuts,有机合成中的保护基团(ProtectiveGroups in Organic Synthesis),第二版,John Wiley&Sons,纽约1991)。
式(XI)的内酰胺可以例如通过两种方法从式(XII)的ω-烷氧基内酰胺起始来制备。其可以根据下面的反应式,在酸催化剂例如硫酸,乙酸或氯化铵存在下,和任选地在稀释剂例如二氯甲烷或乙腈存在下,与式(XIII)的芳烃反应:
或者,其可以根据下面的反应式,在稀释剂例如四氢呋喃的存在下与式(XIV)的芳基格利雅化合物反应[参见Org.Prep.Proced.Int.25,255(1993)]:
在式(XII)中,R28代表甲基或乙基。在式(XIV)中,Hal代表氯,溴或碘。
式(XII)的ω-烷氧基内酰胺是已知的,并且其中一些可以购得。其可以例如在甲醇或乙醇存在下通过阴极或四硼酸钠还原从相应的未取代的酰亚胺或者通过阳极氧化从未取代的内酰胺制备(参见例如有机化学杂志(J.Org.Chem.)56,1822(1991);合成(Synthesis)1980,315)。
式(XIII)的芳烃是苯衍生物,其一般是已知的或者其可以通过使用各种各样的一般已知的有机化学方法来制备。
式(XIV)芳基格利雅化合物可以以常规方式从相应的芳基卤化物和镁制备。芳基卤化物一般是有机化学已知的化合物。
式(XI)的内酰胺也可以例如根据下面的反应式通过在沸点用由碳酸铵和甲酸制备的试剂环化式(XV)取代的ω-苯甲酰基羧酸来制备[参见Recl.Trav.Chim.Bays-Bas81,788(1962)]:
这里所需要的式(XV)的ω-苯甲酰基羧酸可以例如通过根据下面的反应式,在路易丝酸例如氯化铝存在下和如果适当在稀释剂例如苯的存在下,使式(XVI)的二羧酸酸酐与式(XIII)的芳烃反应来制备[参见Recl.Trav.Chim.Bays-Bas81,788(1962)]:
这里所需要的酸酐是(琥珀酸酐和戊二酸酸酐)或者过去是(己二酸酸酐)商业上可获得的[关于己二酸酸酐的制备参见例如Chem.Ber.120,285(1987)]。
如果本发明式(I)活性化合物中的Ar2代表上面给出的例如式(I-b)中任选被取代的联苯基,则式(XI-a)的相应的联苯基内酰胺可以在这里所描述的有利的变化方法中,通过上述和下面进一步描述的方法(C)的方法,根据下面的反应式,通过使某些式(XVII)的苯基内酰胺与式(VI)的硼酸反应来制备:
其中X1代表溴或碘的式(XVII)苯基内酰胺是一系列其制备如上所述的式(XI)的化合物。其中X1代表三氟甲磺酰基的式(XVII)苯基内酰胺可以类似于方法(C)从相应的其中Ar2被R4=羟基取代的式(XI)的化合物制备。
式(II)的新的氨基酮可以例如根据下面的反应式还原在方法(A.b)中也是新的之式(XVIII)的硝基酮的硝基来制备:
该还原作用可以通过催化氢化或者其它还原硝基的一般已知的方法来进行(参见,例如Houben-Weyl,有机化学方法(Methoden derOrganischen Chemie),Georg Thieme Verlag Stuttgart,11/1卷,394-409和4/1c卷,490-506)。优选的方法是在酸性介质中进行该反应,因为式(II)的氨基酮优选分离为盐。
式(XVIII)的硝基酮可以例如通过根据下面的反应式,在稀释剂例如甲醇,乙醇,其它低级脂肪醇或四氢呋喃存在下和在酸结合剂例如氢化钠或碱金属醇化物存在下,优选使用相应的醇为稀释剂,缩合式(XXI)的ω-氯代烷基苯基酮来制备:
式(XXI)的ω-氯代烷基苯基酮是商业上可获得的,已知的或者可以通过使用已知方法制备,例如通过式(XXII)的相应的苯衍生物与3-氯代丙酰氯,4-氯代丁酰氯或5-氯代戊酸氯的弗瑞德-克来福特酰化作用来制备(参见下文)。
式(XIX)的硝基甲基苯是已知的或者可以以已知的方法制备,例如通过在侧链硝化相应的甲苯或者使相应的苄基卤化物与亚硝酸银反应[参见例如J.Am.Chem.Soc.77,6269(1955);J.Am.Chem.Soc.86,2681(1964);Houben-Weyl,有机化学方法(Methoden der OrganischenChemie),Georg Thieme Verlag Stuttgart,10/1卷,46-57(卤素取代)和E16卷,145-154(两种方法)]。所需要的甲苯或苄基卤一般是有机化学已知的化合物。
其中n等于1的式(XVIII)的硝基酮(XVIII-a)可以例如通过在稀释剂例如甲醇,乙醇或另外的低级脂肪醇存在下和在酸结合剂存在下,例如优选使用相应的醇的碱金属醇化物为稀释剂,根据下面的反应式,通过式(XIX)的硝基甲基苯与式(XX)的苯基乙烯基酮的麦克尔加成来制备(参见例如J.Prakt.Chem.,Series4,1,57(1955);Houben-Weyl,有机化学方法(Methoden der Organischen Chemie),Georg ThiemeVerlag Stuttgart,10/1卷,199-206):
式(XX)的苯基乙烯基酮可以例如通过在酸结合剂例如乙酸钾存在下和在稀释剂例如甲醇存在下,根据下面的反应式,从式(XXI-a)的β-氯代丙酰苯酮消除氯化氢来制备,式(XXI-a)例如是可通过用3-氯代丙酰氯对相应的式(XXII)的苯衍生物进行弗瑞德-克来福特酰化获得的[参见,例如J.Prakt.Chem.,Series4,1,57(1955)]:
一些式(XXII)的苯衍生物是商业上可获得的或已知的,或者其可以通过芳烃化学一般已知的方法来制备。
式(XX)的苯基乙烯基酮也可以通过根据下面的反应式,使式(XXIII)的甲基苯氧肟酸O-甲基酯与乙烯基溴化镁反应来制备:
一些式(XXIII)的甲基苯氧肟酸O-甲基酯是已知的(“Weinreb酰胺”),或者其可以通过已知的方法制备,例如从相应的苯甲酸衍生物制备[参见,例如四面体快报Tetrahedron Lett.22,3815(1981)〕。
因为一些式(XX)的苯基乙烯基酮是不稳定的,其在制备式(XVIII-a)的硝基酮的优选的变化方法中,直接与式(XIX)的硝基甲基苯反应。
(XVIII-a)的硝基酮也可以通过根据下面的反应式对式(XXVII)的α-硝基苯乙烯加成式(XXVI)的甲基苯基酮的烯胺,并且在酸性条件下水解反应产物来制备:
在式(XXIV),(XXV)和(XXVI)中,R29和R30与它们所连接的氮原子一起代表环氨基残基,例如1-吡咯烷基,1-哌啶子基或4-吗啉基。
在多数情况下,加成反应以[4+2]-环加成进行来提供可以分离的式(XXV)的1,2-噁嗪N-氧化物衍生物,而且如果需要,反应在非极性稀释剂例如乙醚存在下,在例如-80℃至+20℃温度下进行。如果需要,在甲醇或乙醇存在下,水解使用例如无机酸水溶液例如盐酸来进行[参见,例如Helv.Chim.Acta68,162(1985);四面体45,2099(1989)]。很多情况下,首先通过简单地将1,2-噁嗪-N-氧化物衍生物溶解于甲醇或乙醇中来打开环,得到式(XXIV)化合物是有利的,因为否则会出现得到相应的二酮化合物的不期望的Nef反应作为竞争反应[参见例如四面体45,2099(1989)]。
一些式(XXVI)烯胺是已知的,或者其可以例如通过标准方法从适当被取代的乙酰苯酮和环胺来制备(参见例如有机合成(Org.Syntheses),Vol.58,56,John Wiley&Sons,纽约)。一些所需要的乙酰苯酮是商业上可购得的或者已知的,或者其可以通过芳族化学的已知方法来制备。
一些式(XXVII)的硝基苯乙烯是已知的或者其可以例如通过上面给出的式(XIX)的硝基甲基苯的甲酰化作用来制备(参见,例如Houben-Weyl,有机化学方法(Methoden der Organischen Chemie),Georg Thieme Verlag Stuttgart,E16卷,215)。
式(II)新的氨基酮也可以例如通过根据下面的反应式在方法(A.c)中水解式(XXVIII)的亚胺来制备:
水解可以通过一般已知的方法例如使用盐酸水溶液来进行。这里式(II)的氨基酮也优选分离为其盐,例如作为盐酸盐,如上文进一步描述。
其中n等于1的式(XXVIII)的亚胺(XXVIII-a)可以例如根据下面的反应式通过进行式(XXIX)N-二苯基亚甲基苄基胺与式(XX)的苯基乙烯基酮的麦克尔加成来制备:
加成作用在酸结合剂存在下和在稀释剂例如乙腈或二氯甲烷存在下,和如果需要,在反应助剂存在下,例如在室温下进行。优选的酸结合剂是在作为反应助剂的相转移催化剂例如三乙基苄基氯化铵存在下碱性水溶液例如50%的氢氧化钠水溶液[参见,例如合成通讯(Synth.Commun.)17,211(1987)]。
式(XX)的苯基乙烯基酮的制备在上文所描述。式(XXIX)的N-二甲基亚甲基苄基胺例如通过相应的苄基胺与二苯甲酮反应而获得(参见,例如四面体快报,1978,2641)。为此目的所需要的苄基胺是已知的,或者其可以通过已知的方法制备,例如相应的苄基卤化物的氨解(参见上文)。
进行本发明方法(B)所需要的环O-甲磺酰基肟通过式(III)以一般方式定义。在该结构式中,Ar2和n两者优选具有已经提及的与描述式(I)的环胺相关的作为优选的那些定义。式(III)的O-甲磺酰基肟是新的。
式(III)的O-甲磺酰基肟可以例如通过根据下面的反应式首先通过已知的方法将式(XXXI)的环α-芳基酮转化成其式(XXX)的肟,然后使这些化合物通过醇的甲磺酰化作用方法与甲磺酰氯反应来制备:
式(XXXI)的环α-芳基酮可以例如根据下面的反应式,通过用常规方法环氧化式(XXXIII)的1-芳基环烯,例如使用间-氯过苯甲酸,得到式(XXXII)的环氧烷,并且然后通过酸处理将其异构体化来制备[参见,例如四面体30,2027(1974)]:
当然,也可以使通过不同途径得到的式(XXXII)的环氧烷异构化成式(XXXI)的环α-芳基酮,例如通过使其在含20%硫酸的氯仿溶液中振荡。
式(XXXIII)的1-芳基环烯可以例如通过在通常的格利雅条件下使上文详细描述的式(XIV)的芳基格利雅化合物与式(XXXV)的酮反应,并且将由此得到的式(XXXIV)的环苄基醇脱水来制备,例如根据下面的反应式,以该方法获得:
脱水作用可以例如通过在例如0℃至20℃下,将醇溶解于少量极性溶剂例如己烷中并与半浓缩硫酸搅拌来进行[参见,例如四面体30,2027(1974)]。
式(XXXV)的酮,环丁酮,环戊酮和环己酮都是商业上可得的。
进行本发明方法(B)还需要的芳基格利雅化合物通过式(IV)以一般方式定义。在该结构式中,Ar1优选具有已经提到的与描述式(I)环亚胺相关的作为优选的那些定义。
式(IV)的芳基格利雅化合物是已知的,或者其可以通过从相应的芳基卤化物和镁的格利雅反应来制备。芳基卤化物一般是有机化学已知的化合物。
只要X1代表溴或碘,则进行本发明方法(C)所需要的式(V)的环亚胺是本发明通式(I)的化合物的子集,并且可以例如通过方法(A)或(B)来制备。如果X1代表三氟甲磺酰基,则式(V-a)的化合物可以通过根据下面的反应式,在酸结合剂例如吡啶的存在下和如果需要在稀释剂存在下,用由通过方法(A)或(B)制备的式(I-f)的羟基化合物与三氟甲磺酰氯或三氟甲磺酸酸酐反应来制备:
进行本发明方法(C)还需要的硼酸通过式(VI)以一般方式定义。在该结构式中,R4-1优选具有已经提到的与描述式(I-b)的环亚胺相关的作为优选的那些定义。
式(VI)的芳香硼酸是已知的,或者其可以通过已知的方法制备[参见,化学评述(Chem.Rev.)45,2457(1995);纯应用化学(Pure Appl.Chem.)66,213(1994)]。
进行本发明方法(D)所需要的式(I-b)的环亚胺是本发明通式(I)的化合物的子集,并且可以例如通过方法(A)至(C)来制备。
进行本发明方法(D)还进一步需要的化合物通过式(VII)定义。在该结构式中,R15,R16,G,p,q和r各自优选具有已经提到的与描述式(I)的环亚胺相关的作为优选的那些定义。Ab代表常规的离去基团,例如卤素,特别是溴或碘;烷基磺酰基氧基,特别是甲基磺酰基氧基;或者任选被取代的芳烃磺酰基氧基,特别是苯基磺酰基氧基,对-氯磺酰基氧基或对-甲苯基磺酰基氧基。
式(VII)的化合物一般是已知的有机化学化合物。
如果需要,本发明方法(A)在合适的酸受体存在下进行。合适的酸受体是所有常规无机碱或有机碱。优选包括碱土金属或碱金属氢氧化物,氨化物,醇化物,乙酸盐,碳酸盐或碳酸氢盐,例如氢氧化钠,氢氧化钾或氢氧化胺,氨化钠,二异丙基氨化锂,甲醇钠,乙醇钠,叔丁醇钾,乙酸钠,乙酸钾,乙酸钙或乙酸铵,碳酸钠,碳酸钾或碳酸胺,碳酸氢钠或碳酸氢钾,和季胺类,例如三甲胺,三乙胺,三丁基胺,N,N-二甲基苯胺,N,N,-二甲基-苄基胺,吡啶,N-甲基哌啶,N-甲基吗啉,N,N-二甲基氨基吡啶,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
如果需要,本发明方法(A)在稀释剂存在下进行。合适的稀释剂是水,有机溶剂和其混合物。例子包括脂肪族,脂环族或芳香族烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤化烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷,三氯乙烷或四氯乙烯;醚类,例如二乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷,二乙二醇二甲基醚或茴香醚;酮类,例如丙酮,丁酮,甲基异丁基酮或环己酮;腈类,例如乙腈,丙腈,正-或异-丁腈或苄腈;酰胺类,例如甲酰胺,N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基-吡咯烷酮或六甲基磷酸三酰胺;N-氧化物,例如N-甲基吗啉-N-氧化物;酯类,例如乙酸甲酯,乙酸乙酯或乙酸丁酯;亚砜类,例如二甲亚砜;砜类,例如环丁砜;醇类,例如甲醇,乙醇,正-或异-丙醇,正-,异-,仲-或叔-丁醇,乙二醇,丙-1,2-二醇,乙氧基乙醇,甲氧基乙醇,二乙二醇单甲基醚,二乙二醇单乙基醚;水。
本发明方法(A)的反应温度可以在相当宽的范围内变化。一般情况下,该方法在-50℃和+150℃之间的温度下进行,优选在-20℃和+100℃之间。
本发明方法(A)中,式(II)的化合物的盐和碱一般以等摩尔量使用。
在优选的变化方法中,式(II)的氨基酮通过途径(A.a)至(A.c)之一进行,并且不用分离而通过加入根据方法(A)的碱在单釜反应中环缩合。
进行本发明方法(B)合适的稀释剂是惰性有机溶剂及其混合物。例子包括;脂肪族,脂环族或芳香族烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤化烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷,三氯乙烷或四氯乙烯;醚类,例如二乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷,二乙二醇二甲基醚或茴香醚。
优选使用式(IV)的格利雅化合物的乙醚溶液和式(III)的O-甲基磺酰基肟的烃溶液。
本发明方法(B)的反应温度可以在相当宽的范围内变化。一般情况下,反应在-100℃和+50℃之间的温度下进行,优选在-80℃和+30℃之间。
在实施本发明方法(B)中,以摩尔比1∶1至3∶1,优选1∶1至2∶1使用式(IV)的格利雅化合物和式(III)的O-甲基磺酰基肟。
进行本发明方法(C)的合适的催化剂是钯(0)配合物,优选使用例如四(三苯基膦)钯。
进行本发明方法(C)的合适的酸受体是无机碱或有机碱。优选包括碱土金属或碱金属氢氧化物,乙酸盐,碳酸盐或碳酸氢盐,例如氢氧化钠,氢氧化钾,氢氧化钡或氢氧化胺,乙酸钠,乙酸钾,乙酸钙或乙酸铵,碳酸钠,碳酸钾或碳酸胺,碳酸氢钠或碳酸氢钾,碱金属氟化物,例如氟化铯,和季胺类,例如三甲胺,三乙胺,三丁基胺,N,N-二甲基苯胺,N,N,-二甲基-苄基胺,吡啶,N-甲基哌啶,N-甲基吗啉,N,N-二甲基氨基吡啶,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
进行本发明方法(C)的合适的稀释剂是水,有机溶剂和其混合物。例子包括脂肪族,脂环族或芳香族烃,例如石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤化烃,例如氯苯,二氯苯,二氯甲烷,氯仿,四氯化碳,二氯乙烷,三氯乙烷或四氯乙烯;醚类,例如二乙醚,二异丙基醚,甲基叔丁基醚,甲基叔戊基醚,二噁烷,四氢呋喃,1,2-二甲氧基乙烷,1,2-二乙氧基乙烷,二乙二醇二甲基醚或茴香醚;醇类,例如甲醇,乙醇,正-或异-丙醇,正-,异-,仲-或叔-丁醇,乙二醇,丙-1,2-二醇,乙氧基乙醇,甲氧基乙醇,二乙二醇单甲基醚,二乙二醇单乙基醚。
本发明方法(C)的反应温度可以在相当宽的范围内变化。一般情况下,该方法在0℃和+140℃之间的温度下进行,优选在50℃和+100℃之间。
在实施本发明方法(C)中,以摩尔比1∶1至3∶1,优选1∶1至2∶1使用式(VI)的硼酸和式(V)的化合物。一般情况下,对于每摩尔式(V)的化合物使用0.005至0.5mol,优选0.01mol至0.1mol催化剂。一般使用过量的碱。
本发明方法(D)优选在合适的酸受体存在下进行。合适的酸受体是所有常规无机碱或有机碱。这些优选包括碱土金属或碱金属氢化物,氢氧化物,氨化物,醇化物,乙酸盐,碳酸盐或碳酸氢盐,例如氢化钠,氢氧化钠,氢氧化钾或氢氧化胺,氨化钠,二异丙基氨化锂,甲醇钠,乙醇钠,叔丁醇钾,乙酸钠,乙酸钾,乙酸钙或乙酸铵,碳酸钠,碳酸钾或碳酸胺,碳酸氢钠或碳酸氢钾,和季胺类,例如三甲胺,三乙胺,三丁基胺,N,N-二甲基苯胺,N,N,-二甲基-苄基胺,吡啶,N-甲基哌啶,N-甲基吗啉,N,N-二甲基氨基吡啶,二氮杂双环辛烷(DABCO),二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
本发明方法(D)可以在合适的相转移催化剂存在下进行。这些催化剂的例子包括:四丁基碘化铵,四丁基溴化铵或四丁基氯化铵,三丁基甲基溴化磷,三甲基-C13/C15-烷基氯化铵或三甲基-C13/C15-烷基溴化铵,甲基硫酸二苄基二甲基铵,二甲基-C12/C14-烷基苄基氯化铵,15-crone-5,18-crone-6或三-[2-(2-甲氧基乙氧基)-乙基]-胺。
本发明方法(D)优选在稀释剂存在下进行。合适的稀释剂例如是方法(A)中列出的所有的溶剂。
本发明方法(D)的反应温度可以在相当宽的范围内变化。一般情况下,在-20℃和+100℃之间的温度下进行该反应,优选在0℃和60℃之间。
进行本发明方法(D)时,一般以大约等摩尔量使用起始物。但是,也可以以过量使用式(VII)的化合物。
本发明方法(E)的反应是本领域技术人员已知的衍生化反应,特别是羧酸酯和酮的衍生化反应(参见,例如Houben-Weyl,有机化学方法,Georg Thieme Verlag,Stuttgart,Vol.VII/2,特别是1912ff;Vol.VIII,关于羧酸酯和其衍生物;Vol.E5,特别是p.812ff和这里引述的文献)
本发明方法的反应可以在常压或高压下进行;优选在大气压下进行。根据有机化学常规方法进行后处理。终产物优选通过结晶,色谱纯化或者通过去除挥发成分,如果需要在减压下,来纯化。
本发明活性化合物适于防治动物害虫,特别是农业,林业,储藏品保护和材料保护,以及卫生领域所遇到的昆虫,蛛形纲和线虫,并且具有好的植物耐受性,并且对温血动物毒性低。这些化合物对于一般敏感性和抗性物种是有活性的,并且在害虫发育的所有阶段或部分阶段有效。上述害虫包括:
等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber。
多足纲目(Diplopoda),例如Blaniulus gutttulatus。
唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.)。
综合纲目(Symphyla),例如Scutigerella immaculata。
缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina)。
弹尾目(Collembola),例如Onychiurus armatus。
直翅目(Orthoptera),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpaspp.),热带飞蝗(Locusta migratoria migratorioides),长额负蝗(Melanoplusdifferentialis)和Schistocerca gregaria。
革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia)。
等翅目(Isoptera),例如白蚁属(Reticulitermes spp.)。
虱目(Anoplura),例如头虱(Pediculus humanus corpori s),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.)。
食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalineaspp.。
缨翅目(Thysanoptera),例如温室条蓟马(Hercinothripsfemoralis)和棉蓟马(Thrips tabaci)。
异翅亚目(Heteroptera),例如褐盾蝽属(Eurygaster spp.),Dysdercusintermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimex lectularius),Rhodnius prolixus和吸血猎蝽属(Triatoma spp.)。
同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisiatabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphis gossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphisfabae),Doralis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),Phyll oxera vastatrix,Pemphigus spp.,Macrosiphum avenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodonhumuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoasca spp.),Euscelis bilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecaniumcorni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotushederae,粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletisblancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutellamaculipennis),天幕毛虫(Malacosoma neustria),Euproctischrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrixthurberiella),Phyllocnisti citrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Earias insulana),夜蛾属(Heliothis spp.),甜菜夜蛾(Laphygma exigua),甘蓝夜蛾(Mamestrabrassicae),Panolis flammea,斜纹夜蛾(Prodenia litura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsapomonella),粉蝶属(Pieris spp.),螟(Chilo spp.),Pyrausta nubilalis,Ephestia kuehniella,大黄螟(Galleria mellonella),袋衣蛾(Tineolabisselliella),网衣蛾(Tinea pellionella),褐织叶蛾(Hofmannophilapseudospretella),Cacoecia podana,Capua reticulana,云杉卷叶蛾(Choristoneura fumiferana),葡萄果蠹蛾(Clysia ambiguella),茶黄卷叶蛾(Homona magnanima)和栎绿卷叶蛾(Tortrix viridana)。
鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,Bruchidius obtectus,大豆象(Acanthoscelidesobtectus),家天牛(Hylotrupes b ajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsa decemlineata),Phaedon cochleariae,叶甲属(Diabroticaspp.),油菜兰跳甲(Psylliodes chrysocephala),墨西哥豆瓢虫(Epilachnavarivestis),Atomaria spp.,锯胸谷盗(Oryzaephilus surinamens),象甲属(Anthonomus spp.),米象属(Sitophilus spp.),Otiorrhynchussulcatus,香蕉蛛基象甲(Cosmopolites sordidus),Ceuthorrhynchusassimilis,苜宿叶象甲(Hypera posttica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenuespp.),粉蠹(Lyctus spp.),Meligethes aeneus,蛛甲属(Ptinus spp.),金黄蛛甲(Niptus hololeucus),麦蛛甲(Gibbium psylliodes),拟谷稻属(Tribolium spp.),黄粉甲(Tenebrio molitor),扣甲属(Agriotes spp.),金针虫属(Conoderus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis)和Costelytra zealandica。
膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomorium pharaonis),和胡蜂(Vespa spp.)。
双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophila melanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphoraerythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(Oestrus spp.),皮蝇属(Hydoderma spp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinellafrit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyiahyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipudosa)。
蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis),和角叶蚤属(Ceratophyllus spp.)。
蛛形纲(Arachnida),例如Sciopio maurus,黑寡妇球腹蛛(Latro dect us mactans)。
蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argasspp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssus gallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilusspp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyomma spp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptes spp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),和红叶螨属(Tetranychus spp.)。
植物寄生线虫包括短体线虫属(Pratylenchus spp.),相似穿孔线虫(Radpholus similis),起绒草茎线虫(Ditylenchus dipsaci),半穿刺线虫(Tylenchulus semipenetrans),异皮线虫属(Heterodera spp.),根结线虫属(Meloidogyne spp.),Aplelenchoides spp.,长针线虫属(Longidorusspp.),剑线虫属(Xiphinema spp.),毛刺线虫属(Trichodorus spp.)。
本发明式(I)的活性化合物抗辣根猿叶甲(Phaedon cochleariae)幼虫,草地粘虫(Spodopterafrugiperda)毛虫,黑尾叶蝉(Nephotettixcincticeps)幼虫,桃蚜(Myzus persicae)和所有阶段的棉红蜘蛛(Tetranychus urticae)特别具有出色活性
活性化合物可以转变成常规制剂,例如溶液、乳液、可湿性粉末、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉末、颗粒剂、混悬乳油、浸有活性化合物的天然的和合成的材料,和包裹在聚合物中的细微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与扩充剂即液体溶剂和/或固体载体混合,必要时,使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
用水作扩充剂的情况下,也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯或二氯甲烷,脂肪烃,如环己烷或石蜡,例如矿物油馏份,矿物油和植物油,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲亚砜,以及水。
合适的固体载体是:
例如铵盐和磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的适合的固体载体有:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如,木素亚硫酸废液和甲基纤维素。
制剂中,可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可以使用染料,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
本发明活性化合物可以以其商售制剂存在以及由这些制剂制备的使用形式存在,作为与其它活性化合物例如杀虫剂、引诱剂、消毒剂、杀菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂的混合物。杀虫剂包括例如磷酸酯,氨基甲酸盐,羧酸酯,氯代烃,苯基尿和特别是通过微生物制备的物质。
特别有利的混合物成分的例子如下:
杀真菌剂:
2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基-嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苄基)甲酰苯胺;(E)-2-甲氧基亚胺基-N-甲基-2-(2-苯氧基苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧基]-苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚胺基[α-(邻-甲苯基氧基)-邻-甲苯基]乙酸乙酯;2-苯基苯酚(OPP),aldimorph,氨丙磷酸,敌菌灵,戊环唑,
苯霜灵,邻碘酰苯胺,苯菌灵,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌消,乙菌利,代森锰,霜尿氰,环唑醇,酯菌胺,
双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇,二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,多果定,氨噁唑酮,
克瘟散,epoxyconazole,乙嘧酚,土菌灵,
氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,fludioxonil,氟氯菌核利,fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋霜灵,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双瓣醋酸盐,异稻瘟净(IBP),异菌脲,稻瘟灵,
春雷霉素,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜,和波尔多液,
代森锰铜,代森锰,代森锰锌,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,噻菌胺,腈菌唑,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,氧化萎锈灵,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,
五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,氟嘧唑,噻菌灵,噻菌腈,甲基硫菌灵,福美双,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
稻纹散,乙烯菌核利,
代森锌,福美锌。
杀细菌剂:
bronopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,AC303630,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,avermectin,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,
苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,GA157419,CGA184699,chloethocarb,chlorethoxyfos,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,顺式-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,三环锡,氯氰菊酯,灭蝇胺,
溴氰菊酯,内吸磷-M,内吸磷-S,甲基内吸磷,杀螨隆,二嗪磷,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌噁磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,噁唑磷,ivermectin,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,moxidectin,
二溴磷,NC184,NI25,nitenpyram,
氧乐果,杀线威,亚砜吸磷,异砜磷,
对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyradaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
RH5292,
蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,
tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,YI5301/5302,zetamethrin。
也可以是与其它已知活性成分例如除草剂,或者与化肥和生长调节剂的混合物。
本发明活性化合物还可以以其商售制剂存在和以由这些制剂制备的作为与增效剂的混合物的使用形式存在。增效剂是提高活性化合物作用而加入的但其自身不必有活性的化合物。
由商售制剂制备的使用形式的活性化合物含量可以在宽范围内变化。使用形式的活性化合物的浓度是0.0000001-95%(重量)活性化合物,优选0.0001-1%(重量)。
以适于这些使用形式的常规方式应用这些化合物。
当用来杀卫生领域害虫和储存产品害虫时,这些活性化合物对木材和粘土具有极好的有后效的作用,以及对用石灰处理过的物质上的碱的好的稳定性。
本发明活性化合物不仅对杀植物,卫生领域和储存产品害虫有活性,而且还用于兽药领域,杀动物寄生虫(定居寄生虫),例如硬蜱,软蜱,马痒螨,恙螨,蝇(叮和吮),寄生蝇幼虫,虱,头虱,鸟虱和蚤。
这样的寄生虫包括:
虱目(Anolpurida),例如,血虱属(Haematopinus spp.),长颚虱(Linognathus spp.),虱属(Pediculus spp.),阴虱属(Phtirus spp.),管虱属(Solenopotes spp.)。
食毛目咬虱(Mallophagida)和Amblycerina及Ischnocerina亚目,例如毛羽虱属(Trimenopon spp.),Menopon spp:,巨羽虱属(Trinotonspp.),牛羽虱属(Bovicola spp.),Werneckiella spp.,Lepikentronspp.,Damalina spp.,Trichodectes spp.,Felcola spp.。
双翅目(Diptera)和长角亚目(Nematocerina)和B rachycerina亚目,例如伊蚊(Aedes spp.),斑按蚊属(Anopheles spp.),库蚊(Culex spp.),蚋属(Simulium spp.),全毛真蚋(Eusimulium spp.),白蛉(Phlebotomusspp.),罗蛉属(Lutzomyia spp.),库蠓(Culicoides spp.),斑虻(Chrysopsspp.),瘤虻(Hybomitra spp),Atylotus spp.,虻属(Tabanus spp.),麻虻属(Haematopota spp.),Philipomyia spp.,Braula spp.,Musca spp.,齿股蝇属(Hydrotuea spp.),螫蝇(Stomoxys spp.),Haematobia spp.,Morellia spp.,厕蝇(Fannia spp.),Glossina spp.,Calliphora spp.,Lucilia spp.,Chrysomyia spp.,Wohlfahrtia spp.,别麻蝇(Sarcophagaspp.),Oestrus spp.,皮蝇(Hypoderma spp.),Gasterophilus spp.,虱蝇(Hippobosca spp.),Lipoptena spp.,和Melophagus spp.。
蚤目(Siphonapterida),例如,蚤属(Pulex spp.),Ctenocephalidesspp.,鼠蚤(Xenopsylla spp.),和角叶蚤(Ceratophyllus spp.)。
异翅亚目(Heteropterida),例如,臭虫属(Cimex spp.),吸血猎蝽属(Triatoma spp.),Rhodnius spp.,和全圆蝽属(Panstrongylus spp.)。
非蠊目(Blattarida),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),德国小蠊(Blattela germanica),非蠊属(Supellaspp.)。
螨(Acarida)亚类,和后胸气门目(Metastigmata)和中胸气门目(Mesostigmata),例如,隐喙蜱属(Argas spp.),喙蜱属(Ornithodorusspp.),耳残喙蜱(Otabius spp.),硬蜱(Ixodes spp.),花蜱属(Amblyommaspp.),牛蜱属(Boophilus spp.),矩头蜱(Dermacentor spp.),Haemophysalis spp.,璃眼蜱(Hyalomma spp.),头蜱属(Rhipicephalusspp.),鸡皮刺螨(Dermanyssus spp.),瑞立绦虫(Raillietia spp.),Pneumonyssus spp.,Sternostoma spp.,和Varroa spp.。
Actinedida(恙螨亚目,Prostigmata)和Acaridida(Astigmata),例如Acarapis spp.,姬螯螨属(Cheyletiella spp.),Ornithocheyletia spp.,Myobia spp.,疥螨(Psorergates spp.),蠕形螨(Demodex spp.),恙螨(Trombicula spp.),Listrophorus spp.,粗脚粉螨(Acarus spp.),酪螨(Tyrophagus spp.),嗜木螨(Caloglyphus spp.),Hypodectes spp.,翼衣螨属(Pterolichus spp.),恙螨(Psoroptes spp.),恙螨(Chorioptes spp.),Octodectes spp.,疥螨(Sarcoptes spp.),Notoedres spp.,足螨(Knemidocoptes spp.,),Cytodites spp.,和Laminosioptes spp.。
例如它们具有杀丝光绿蝇(Lucilla cuprina)全部幼虫阶段和扁虱多色花蜱(Amblyomma variegatum)全部发育阶段的出色的活性。
本发明式(I)活性化合物也适于杀死侵染农业生产家畜的节肢动物门,所述家畜是例如牛,绵羊,山羊,马,猪,驴,骆驼,水牛,兔子,鸡,火鸡,鸭,鹅,蜜蜂,其它宠物,例如狗,猫,笼养的鸟和鱼缸养殖鱼,和称之为实验室动物的动物,例如仓鼠,豚鼠,大鼠和小鼠。通过杀死这些节肢动物门,可以避免家畜死亡并且避免产品量的减少(产品例如肉,奶,羊毛,皮革,蛋,蜂蜜等),因此通过使用本发明活性化合物可以实现更经济更简单的动物的喂养。
在兽药领域,本发明活性化合物以已知方式通过肠给药,例如以片剂,胶囊,顿服水剂,顿服药,颗粒剂,糊剂,巨丸剂,通过进食方法和栓剂的形式;通过肠胃外给药,例如通过注射(肌内,皮下,静脉内,腹膜内等),埋入,通过鼻给药,通过以例如浸渍或浸浴,喷洒,涂施和点施,洗用和撒粉的形式皮肤使用,也可以借助于含有活性化合物的用模子做的物品,例如颈圈,耳饰,尾饰,腿带,笼头,标记物等而使用。
当对牲畜,家禽,宠物等使用时,本发明式(I)活性化合物可以作为以1-80%重量比的量含有活性化合物的制剂(例如粉末剂,乳剂,可流动性组合物)而被使用,直接使用或者稀释100-10000倍后使用,或者可以用化学浴形式。
另外,还发现本发明式(I)化合物还具有杀破坏工业物质的昆虫的有效的杀虫作用。
作为优选例子可以提到下面的昆虫,但是不受此限制:
甲虫,例如
家天牛(Hylotrupes bajulus),Chlorophorus pilosis,家具窃蠹(Anobium punctatum),Xestobium rufovillosum,Ptilinus pecticornis,Dendrobium pertinex,Ernobius mollis,Priobium carpini,欧洲竹粉蠹(Lyctus brunneus),Lyctus africanus,平颈粉蠹(Lyctus planicollis),Lyctuslinearis,Lyctus pubescens,Trogoxylon aequale,Minthesrugicollis,小蠹虫种(Xyleborus spec.),Tryptodendron spec.,Apate monachus,B ostrychuscapucins,Heterobostrychusbranneus,Simoxylonspec.,和竹长蠹(Dinoderus minutus)。
膜翅目(Dermapterans),例如
钢青小树蜂(Sirex juvencus),枞大树蜂(Urocerus gigas),Urocerusgigas taignus和Uro c erus augur。
白蚁,例如
Kalotermes flavicollis,Cryptotermes brevis,Heterotermes indicola,Reticulitermesflavipes,Reticulitermessantonensis,Reticulitermeslucifugus,澳洲白蚁(Mastotermes darwiniensis),Zootermopsis nevadensis和台湾家白蚁(Coptotermesformosanus)。
Bristle-tail,例如西洋衣鱼(Lepisma saccharina)。
本说明书中所涉及的工业材料理解为非生命材料,例如,优选塑料,粘合剂,胶料,纸和纸板,皮革,木材和木材加工产品以及涂料。
要保护使不受昆虫侵染的材料非常特别优选是木材和木材加工产品。
可以用本发明成分或含有这样一种成分的混合物保护的木材和木材加工产品例如是,建筑木材加工品,木梁,铁轨枕木,建桥木料,码头,木制运载工具,箱子,制模板,容器,电线杆,木桶,木窗,木门,胶合板,颗粒板,接合物,或者在房屋建筑或细木工行业很普通使用的木产品。
本发明活性化合物可以以乳油形式或者一般的常规制剂使用,例如粉末剂,颗粒剂,溶液,混悬剂,乳剂或糊剂。
提到的制剂可以以本身已知的方法制备,例如通过混合活性化合物和至少一种溶剂或稀释剂,乳化剂,分散剂和/或粘合剂或固定剂,水驱避剂,如果需要,干燥剂和UV稳定剂和,如果需要,着色剂和颜料和其它加工助剂。
用于保护木料和木制品的杀虫剂组合物或提浓物以0.0001-95%(重量)浓度含有本发明活性化合物,特别是0.001-60%(重量)。
使用的试剂或提浓物的量取决于害虫的物种和发生,并取决于介质。施用的最佳比例每种情况下可以通过试验系列来决定。但是,一般情况下,使用以要保护的材料为基础的0.0001-20%(重量),优选0.001-10%(重量)的活性化合物就足够了。
使用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或油或油型有机化学溶剂或低挥发性溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水和,如果需要,乳化剂和/或湿润剂。
优选使用的有机化学溶剂是具有大于35的挥发数和高于30℃,优选高于45℃的闪点的油或象油一样的溶剂。用作具有低挥发性并且在水中不溶解的这类油和象油一样的溶剂的物质是合适的矿物油或其芳香烃馏分,或者含有矿物油的溶剂混合物,优选石油溶剂,石油和/或烷基苯。
有利地使用的物质是沸点范围是170-220℃的矿物油,沸点范围是170-220℃的石油溶剂,沸点范围是250-350℃的锭子油,沸点范围是160-280℃的石油或芳香烃,松节油等。
在优选的实施方案中,使用沸点范围是180-210℃的液体脂肪烃或者沸点范围是180-220℃的芳香烃和脂肪烃的高沸点混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
具有大于35的挥发数和高于30℃,优选高于45℃闪点的低挥发性有机油或油型溶剂可以部分替换成高挥发性或中等挥发性的有机化学溶剂,前提是该溶剂混合物也具有大于35的挥发数和高于30℃,优选高于45℃的闪点,并且杀虫剂/杀真菌剂混合物在该溶剂混合物中是可溶解的或可乳化的。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物替换成脂肪族极性有机化学溶剂或溶剂混合物。优选使用的物质是具有羟基和/或酯基和/或醚基的脂肪族有机化学溶剂,例如乙二醇醚,酯等。
本发明范围内使用的有机化学粘合剂是本身已知的合成树脂和/或粘合干燥油,并且可以用水稀释和/或在使用的有机化学溶剂中是可溶解的,可分散的或可乳化的,特别是粘合剂由下面的物质组成或者含有下面的物质:丙烯酸树脂,乙烯树脂,例如聚乙酸乙烯酯,聚酯树脂,缩聚物或加聚物树脂,聚尿烷树脂,醇酸树脂或改性的醇酸树脂,苯酚树脂,烃类树脂,例如茚/苯并呋喃树脂,有机硅树脂,干燥植物油和/或干燥油和/或以天然和/或合成树脂为基础的物理干燥粘合剂。
作为粘合剂使用的合成树脂可以以乳液,分散液或溶液的形式使用。最多10%重量的沥青或沥青状物质也可以作为粘合剂使用。另外,可以使用本身已知的着色剂,颜料,水驱避剂,气味掩蔽物质和抑制剂或防腐蚀剂等。
根据本发明,组合物或提浓物优选含有至少一种醇酸树脂或改性的醇酸树脂,和/或干燥植物油作为有机化学粘合剂。根据本发明,优选使用的物质是油含量大于45%(重量),优选50-68%(重量)的醇酸树脂。
上面提到的粘合剂可以全部或部分替换成固定剂(混合物)或增塑剂(混合物)。这些添加剂是为了防止活性化合物的挥发和结晶或沉淀。优选替换0.01-30%的粘合剂(以使用的100%粘合剂为基础)。
增塑剂来自邻苯二甲酸酯类,例如邻苯二甲酸二丁酯,邻苯二甲酸二辛酯或邻苯二甲酸苄酯丁酯,磷酸酯,例如磷酸三丁酯,己二酸酯,例如己二酸二-(2-乙基己基)酯,硬脂酸酯,例如硬脂酸丁酯或硬脂酸戊酯,油酸酯,例如油酸丁酯,甘油醚或较高分子量的乙二醇醚,甘油酯和对甲苯磺酸酯。
固定剂的化学基础是聚乙烯基烷基醚,例如,聚乙烯基甲基醚,或酮类,例如二苯酮或二苯乙酮(ethylenebenzophenone)。
作为溶剂或稀释剂特别合适的是水,如果需要,以与一种或几种上述有机化学溶剂或稀释剂,乳化剂和分散剂的混合物存在。
特别有效的木材保护作用是通过大量的工业化浸入方法实现的,例如真空,双倍真空或加压方法。
如果需要,即用型组合物可以另外含有其它的杀虫剂和,如果需要,另外一种或几种杀真菌剂。
可以混合的合适的附加成分优选是WO94/29268中提到的杀虫剂和杀真菌剂。该文献中提到的化合物明确地是本申请组成部分。
可以混合的非常特别优选的成分是杀昆虫剂,例如毒死稗,辛硫磷,silafluofin,甲体氯氰菊酯,氟氯氰菊酯,氯氰菊酯,溴氰菊酯,氯菊酯,吡虫啉,NI-25,氟虫脲,氟铃脲和杀虫隆,和杀真菌剂,例如epoxyconazole,己唑醇,戊环唑,环丙唑,戊唑醇,环唑醇,metconazole,抑霉唑,苯氟磺胺,甲苯氟磺胺,氨基甲酸3-碘代-2-丙炔基丁酯,N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明活性化合物的制备和应用可以从下面的实施例说明。
制备实施例
实施例I-1
0℃下,0.825gl-叔丁氧羰基氨基-3-(2,6-二氟苯甲酰基)-1-苯基-丙烷(例如按照实施例VIII-1)与1.6ml三氟乙酸滴加混合。使混合物温热至室温,并且又搅拌3小时。然后在0℃下,用1N氢氧化钠水溶液使混合物呈碱性(pH11)。混合物用乙酸乙酯萃取3次,合并的萃取液用硫酸钠干燥并减压蒸发。得到0.45g(理论量的83%)2-(2,6-二氟苯基)-5-苯基-3,4-二氢-2H-吡咯。
1H-NMR(400MHz,CDCl3)δ[ppm]:1,75(m,1H,CHHCHPh);2,85(m,1H,CHHCHPh);3,00(m,2H,CH2CN);5,80(t,1H,NCHPh);7,20-7,40(m,7H,ArH);7,57(m,1H,ArH)(Ph=苯基)。
实施例I-2
类似于实施例I-1的方法,从0.38gl-叔丁氧羰基氨基-3-(2,6-二氟苯甲酰基)-1-(4’-三氟甲氧基联苯-4-基)-丙烷(例如通过实施例VIII-2的方法)得到0.36g(理论量的96%)2-(2,6-二氟苯基)-5-(4’-三氟甲氧基联苯-4-基)-3,4-二氢-2H-吡咯。
1H-NMR(500MHz,CDCl3)δ[ppm]:2,10(m,1H,),2,75(m,1H,);3,29(t,2H);5,59(t,1H);7,05(t,2H);7,29(d:J~8Hz,2H);7,42(d:J=7,4Hz,2H);7,47(m,1H);7,58(d:J=7,4Hz,2H);7,60(d:J=7,4Hz,2H)。
实施例I-3
类似于实施例I-1的方法,从7.45g1-叔丁氧羰基氨基-3-(2,6-二氟苯甲酰基)-1-(4-溴代苯基)-丙烷(例如通过实施例VIII-3的方法)得到2.24g(理论量的41%)2-(2,6-二氟苯基)-5-(4-溴代苯基)-3,4-二氢-2H-吡咯。
1H-NMR(400MHz,CDCl3)δ[ppm]:1,70(m,1H,CHHCHPh);2,58(m,I H,CHHCHPh);3,00(m,2H,CH 2CN);5,29(t,1H,NCHPh);7,2-7,3(m,5H,ArH);7,56(m,4H,ArH)。
实施例I-4
首先在氩气下将2.02g2-(2,6-二氟苯基)-5-(4-溴代苯基)-3,4-二氢-2H-吡咯(例如得自实施例I-3)加入到20ml二甲氧基乙烷中。先后加入2.02g4-三氟甲氧基硼酸和0.346g四(三苯基膦)钯。15分钟后,加入9.6ml2M碳酸钠水溶液,混合物加热到80℃并搅拌过夜。反应完成后,混合物溶解于水/乙酸乙酯,分离各相,每次用大约100ml乙酸乙酯萃取水相两次。合并的有机相用饱和的氯化钠水溶液洗涤并用硫酸镁干燥。蒸发得到1.90g(理论量的76%)2-(2,6-二氟苯基)-5-(4’-三氟甲氧基联苯-4-基)-3,4-二氢-2H-吡咯(参见实施例I-2)。
类似于实施例序号I-4并且根据一般制备说明,得到下面表1所列的式(I-f)的化合物。
表1
*:柱子:RP18,硅胶(Kromasil),1=125mm,_=3mm;溶剂:乙腈/水;梯度:t=0分钟10/90(体积/体积)=>18分钟100/0;流速:1.5ml/分钟
**:电喷射-四极-质谱。
起始物的制备
γ-乙氧基-γ-丁酸内酰胺
0℃下,首先将9.91g琥珀酰亚胺加入到415ml乙醇中,并且以分份方式加入5.53g硼酸钠。在该温度下,用41/2小时每15分钟滴加2-3滴2N乙醇盐酸盐。接着用更多的酸将混合物酸化至pH3。在0℃下搅拌1小时后,用1%的乙醇氢氧化钾溶液中和混合物,将混合物又搅拌15分钟并蒸发。残余物溶解于水,并且用二氯甲烷萃取三次。经硫酸钠干燥并浓缩后,得到7.16g(理论量的55%)γ-乙氧基-γ-丁酸内酰胺。
实施例XI-1
0℃下,首先加入6.45gγ-乙氧基-γ-丁酸内酰胺和50ml浓硫酸,并且加入18.8ml苯。融化后,混合物在室温下搅拌4天。对于后处理,将混合物倒入冰中,用乙酸乙酯萃取三次,并且合并的萃取物用水洗涤一次和用饱和的氯化钠溶液洗涤一次,干燥并且蒸发。得到8.1g(理论量的100%)γ-苯基-γ-丁酸内酰胺。
1H-NMR(400MHz,d6-DMSO)δ[ppm]:1,75(m,IH);2,23(t,2H);2,45(m,1H);4,67(t,1H);7,26-7,39(m,5H);8,08(br,1H)
实施例XI-2
0℃下,首先加入12.9gγ-乙氧基-γ-丁酸内酰胺,10ml浓硫酸和90ml冰醋酸,并且逐份与共18.8g苯酚混合。融化后,混合物在室温下搅拌2天。对于后处理,将混合物倒入冰中,用乙酸乙酯萃取三次,并且合并的萃取物用水洗涤一次和用饱和的氯化钠溶液洗涤一次,干燥并且蒸发。一段时间后,从水相中结晶出熔点220℃的γ-2-羟基苯基-γ-丁酸内酰胺(XI-2b)(6.4g,理论量的36%)。蒸发得到的残余物与环己烷/乙酸乙酯的1∶1的混合物搅拌,并且吸滤得到4.65g熔点183℃的γ-4-羟基苯基-γ-丁酸内酰胺(XI-2a)。蒸发滤液。从二氯甲烷/己烷中重结晶,又得到3.35g(理论量的45%)γ-4-羟基苯基-γ-丁酸内酰胺。
实施例XVII-2
0℃下,向60ml吡啶中5.23gγ-4-羟基苯基-γ-丁酸内酰胺(例如得自实施例XI-2)滴加10g三氟甲磺酸酸酐。室温下搅拌过夜后,将反应混合物倒入冰中,用10%的盐酸酸化,并用乙酸乙酯萃取三次。干燥后蒸发溶剂,得到6.4g(理论量的70%)熔点127℃的γ-4-三氟甲基磺酰基氧基苯基-γ-丁酸内酰胺。
实施例XI-a-2
氩气下,首先将5.4gγ-4-三氟甲基磺酰基氧基苯基-γ-丁酸内酰胺(例如得自实施例XVII-2)加入到43ml二甲氧基乙烷中。先后加入5.87g4-三氟甲氧基硼酸和1.01g四(三苯基膦)钯。15分钟后,加入28ml2M碳酸钠水溶液,混合物加热到80℃并搅拌过夜。反应完成后,混合物溶解于水/乙酸乙酯,分离各相,水相用乙酸乙酯萃取两次。合并的有机相用饱和的氯化钠水溶液洗涤并干燥。蒸发,得到5.5g(理论量的98%)γ-4’-三氟甲氧基联苯-4-基-γ-丁酸内酰胺,熔点128℃。
实施例XI-3
在装有搅拌器和蒸馏管的3L三口烧瓶中首先加入127.9g甲酸中的199.3g甲酸铵,并且加入从甲苯中重结晶的210g4-溴苯甲酰基丙酸。然后将烧瓶浸入200℃油浴中。60℃下,烧瓶的内含物开始溶解并产生气体。反应大约2小时,蒸馏混合物,底部温度从140℃提高到167℃,直到反应完全。冷却到低于60℃后,小心加入1L二氯甲烷,并且通过真空吸滤过滤器吸滤分离沉淀的盐。有机相用1L水洗涤,硫酸镁干燥,并减压浓缩。为了纯化,粗产物通过1kg硅胶过滤,使用二氯甲烷/乙醇/三乙胺(95∶5∶3),然后从甲基叔丁基醚中结晶。得到38g(理论量的19%)γ-4-溴代苯基-γ-丁酸内酰胺,熔点142℃。
实施例IX-1
首先将3.4gγ-苯基-γ-丁酸内酰胺(例如得自实施例XI-1)加入到63ml四氢呋喃(THF)中,并且在-78℃与9.24ml2.4N丁基锂的正己烷溶液混合。混合物在该温度下搅拌半小时,然后继续冷却下滴加20mlTHF中5.04g碳酸氢二叔丁酯的溶液,混合物在-78℃下又搅拌3小时,然后不冷却搅拌过夜。然后混合物用饱和的氯化铵水溶液水解,用水稀释并用乙酸乙酯萃取三次。合并的有机相用饱和的氯化钠水溶液洗涤并用硫酸镁干燥。蒸发,得到1.54g(理论量的28%)N-叔丁氧羰基-γ-苯基-γ-丁酸内酰胺。
1H-NMR(400MHz,d6-DMSO)δ[ppm]:1,18(s,9H);1,73(m,1H);2,40-2,60(m,3H);5,10(m,1H),7,24(m,2H);7,30(m,1H);7,38(m,2H)
实施例IX-2
首先将1.7gγ-4’-三氟甲氧基联苯-4-基-γ-丁酸内酰胺(例如得自实施例XI-a-l)加入到30ml四氢呋喃(THF)中,并且在-78℃与2.42ml2.4N丁基锂的正己烷溶液混合。混合物在该温度下搅拌半小时,然后继续冷却下滴加10mlTHF中1.27g二碳酸二叔丁酯的溶液,然后去除冷却,混合物在室温下搅拌过夜。然后混合物用饱和的氯化铵水溶液水解,用2N盐酸酸化,用二氯甲烷萃取三次。干燥和蒸发后,通过柱色谱纯化产物(固定相:硅胶;流动相∶环己烷∶乙酸乙酯=5∶1.3至1.1∶1梯度)。得到1.14g(理论量的47%)部分结晶N-叔丁氧羰基-γ-4’-三氟甲氧基联苯-4-基-γ-丁酸内酰胺。
1H-NMR(400MHz,CDCl3)δ[ppm]:1,22(s,9H);1,79(m,1H);2,48-2,60(m,3H);5,17(m,1H);7,36(d,2H);7,46(d,2H);7,71(d,2H);7,80(d,2H)
实施例IX-3
-78℃下,首先向90mlTHF中加入3.24ml二异丙基胺,并且与9.24ml2.4N丁基锂的正己烷溶液混合。混合物在该温度下搅拌半小时。然后滴加20mlTHF中5.02gγ-4-溴代苯基-γ-丁酸内酰胺(例如得自实施例XI-3)的溶液。-78℃下又继续搅拌半小时,然后滴加20mlTHF中5.04g碳酸氢二叔丁酯,使混合物融化并在室温下搅拌过夜。然后混合物用饱和的氯化铵水溶液水解,用2N盐酸酸化并每次用150ml二氯甲烷萃取三次。硫酸镁干燥和蒸发后,通过从二氯甲烷/己烷中结晶来纯化产物。共得到7.61g(理论量的97%)结晶N-叔丁氧羰基-γ-4-溴代苯基-γ-丁酸内酰胺。最纯的结晶馏分(2.34g)在122-124℃熔化。
实施例VIII-1
在-78℃下,首先将0.62g1,3-二氟苯加入到15mlTHF中,与2.4ml2.4N丁基锂的正己烷溶液混合。混合物在该温度下搅拌1小时,然后非常慢地滴加7mlTHF中1.44g N-叔丁氧羰基-γ-苯基-γ-丁酸内酰胺(例如得自实施例IX-1)的溶液。混合物在-78℃下搅拌3小时后不冷却而搅拌过夜。用氯化铵溶液水解后,混合物用乙酸乙酯萃取三次,并且将合并的萃取物干燥并蒸发。从二氯甲烷/己烷中重结晶,得到1.03g(理论量的50%)1-叔丁氧羰基氨基-3-(2,6-二氟苯甲酰基)-1-(4’-三氟甲氧基联苯-4-基)-丙烷。
1H-NMR(400MHz,d6-DMSO)δ[ppm]:1,33(s,9H);1,94(m,2H);2,89(t,2H);4,54(m,1H);7,22(m,3H);7,30(m,4H);7,42(br d,1H);7,60(m,1H)
实施例VIII-2
类似于实施例VIII-1的方法,从0.62g1,3-二氟苯和1.7g N-叔丁氧羰基-γ-4’-三氟甲氧基联苯-4-基-γ-丁酸内酰胺(例如得自实施例IX-2)得到2.23g(理论量的77%)作为油的1-叔丁氧羰基氨基-3-(2,6-二氟苯甲酰基)-1-(4’-三氟甲氧基联苯-4-基)-丙烷。
1H-NMR(400MHz,CDCl3)δ[ppm]:1,40(s,9H);2,20(m,2H);2,97(m,2H);4,75(m,1H);6,93(t,2H);7,28(m,3H);7,38(d,2H);7,53(d,2H);7,58(d,2H)
实施例VIII-3
类似于实施例VIII-1的方法,从0.62g1,3-二氟苯和2.03g N-叔丁氧羰基-γ-4-溴代苯基-γ-丁酸内酰胺(例如得自实施例IX-3)得到2.51g(理论量的93%)1-叔丁氧羰基氨基-3-(2,6-二氟苯甲酰基)-1-(4-溴代苯基)-丙烷,熔点111-115℃。
应用实施例
实施例A
猿叶甲(Phaedon)幼虫试验
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1重量份活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用辣根猿叶甲(Phaedoncochleariae)幼虫侵染。
一定时间后,以%测定杀伤百分率。100%表示所有的甲虫幼虫都已经被杀死;0%表示没有杀死一只甲虫幼虫。
在该项试验中,例如制备实施例I-2的化合物在举例的0.1%活性化合物浓度时,在7天后,表现出100%杀伤程度。
实施例B
粘虫(Spodoptera)试验
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1重量份活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用草地粘虫(Spodopterafrugiperda)毛虫侵染。
一定时间后,以%测定杀伤百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
在该项试验中,例如制备实施例I-2的化合物在举例的0.1%活性化合物浓度时,在7天后,表现出100%杀伤程度。
实施例C
叶蝉(Nephotettix)试验
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1重量份活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理稻幼苗(Oryzaesativa),并在幼苗还湿润的时候用黑尾叶蝉(Nephotettix cincticeps)幼虫侵染。
一定时间后,以%测定杀伤百分率。100%表示所有的叶蝉都已经被杀死;0%表示没有杀死一只叶蝉。
在该项试验中,例如制备实施例I-1的化合物在举例的0.1%活性化合物浓度时,在6天后,表现出100%杀伤程度。
实施例D
瘤额蚜(Myzus)试验
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1重量份活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理被桃蚜(Myzuspersicae)严重侵染的甘蓝叶(Brassica oleracea)。
一定时间后,以%测定杀伤百分率。100%表示所有的蚜虫都已经被杀死;0%表示没有杀死一只蚜虫。
在该项试验中,例如下面的化合物表现出好的活性:
表D
实施例E
叶螨(Tetranychus)试验(OP抗性/浸入处理)
溶剂:3重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1重量份活性化合物与所述量溶剂和所述量乳化剂混合,用含有乳化剂的水将乳油稀释到需要的浓度。
将被所有阶段棉红蜘蛛(Tetranychus urticae)严重侵染的大豆(Phaseolus vulgaris)浸入到期望浓度的活性化合物制剂中。
一定时间后,以%测定活性。100%表示所有的叶螨都已经被杀死;0%表示没有杀死一只叶螨。
在该项试验中,例如制备实施例I-2的化合物在举例的0.001%活性化合物浓度时,在7天后,表现出100%杀伤程度。
实施例F
苍蝇幼虫试验/抑制发育作用
试验动物:所有幼虫阶段的丝光绿蝇(Lucilia cuprina)(OP抗性)
[蛹和成虫(没有与活性化合物接触)]
溶剂:35重量份的乙二醇单甲基醚
35重量份的壬基苯酚聚乙二醇醚
为了制备合适的制剂,3重量份的活性化合物与7重量份的上述溶剂-乳化剂混合物混合,并且用水将得到的乳油稀释到各种情况下需要的浓度。
对于每个浓度,将30-50只幼虫放到玻璃试管中的马肉(1cm3)上,用移液管将500μl试验稀释液加到肉上。将玻璃试管放到塑料杯中,塑料杯底部覆盖海沙,并且保持在控制环境的小室中(26℃±1.5℃,70%相对湿度±10%)。24小时和48小时后检查活性(杀幼虫作用)。幼虫出来后(大约72小时),取出试管,并且在烧杯上盖上多孔塑料盖子。发育期(孵化对照蝇)的11/2倍后,计数孵化的蝇和蛹(pupae/puparia)。
作用的评价标准是48小时后处理的幼虫的死亡数(杀幼虫效果),或者对从蛹孵化成虫的抑制或者抑制蛹化。物质体外作用的评价标准是对蝇发育的抑制作用或者在成虫期之前停止发育。100%杀幼虫活性指在48小时之后所有的幼虫都已经死亡。100%发育抑制活性指没有成虫蝇孵化出。
在该项试验中,例如制备实施例I-1的化合物在举例的1000ppm活性化合物浓度时表现出100%的活性。
实施例G
对多宿主(polyphargus)壁虱若虫的蜕皮试验
试验动物:多色花蜱(Amblyomma variegatium),将其自身吸满的壁虱
溶剂:35重量份的乙二醇单甲基醚
35重量份的壬基苯酚聚乙二醇醚
为了制备合适的制剂,3重量份的活性化合物与7重量份的上述溶剂-乳化剂混合物混合,并且用水将得到的乳油稀释到各种情况下需要的浓度。
将10只自身吸满的若虫在要试验的活性化合物制剂中浸渍1分钟。将动物转移到带有滤纸圆片的平皿(_9.5cm)中并覆盖。若虫保持的控制环境的小室中4星期后,测定蜕皮比例。
100%指所有的动物都经历了正常的蜕皮;0%指没有一只动物经历了正常的蜕皮。
在该项试验中,例如制备实施例I-1和I-2的化合物在举例的1000ppm活性化合物浓度时各种情况下表现出100%的活性。
Claims (3)
1.式(XI)的化合物
其中
n代表1,2或3,
Ar2代表残基
m代表0,1,2或3,
R4代表处于间位或对位的选自卤素,氰基,三-(C1-C6-烷基)-甲硅烷基,-CO-NR10R11,四氢吡喃基或者下面基团之一的取代基
(l)-X-A
(m)-B-Z-D
(n)-Y-E,
R5代表氢,卤素,氰基,硝基,C1-C16-烷基,C1-C16-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C1-C8-烷氧基-C1-C8-烷氧基或-S(O)OR6,
o代表0,1或2,
R6代表任选被氟-或氯-取代的C1-C6-烷基,
R10和R11各自独立地代表氢,C1-C6-烷基,C1-C6-卤代烷基或者代表苯基或苯基-C1-C4-烷基,其各自任选被下面W1所列出的基团一至三取代,
X代表直接键,氧,硫,羰基,羰基氧基,氧基羰基,C1-C4-亚烷基,C2-C4-亚链烯基,C2-C4-亚炔基,C1-C4-亚烷基氧基,C1-C4-氧基亚烷基,C1-C4-硫基亚烷基,C1-C4-亚烷基二氧基或二-C1-C4-烷基亚甲硅基,
A代表苯基,萘基或四氢萘基,其各自任选被下面W1所列出的基团一至四取代,或者代表具有1-4个杂原子,包括0-4个氮原子,0-2个氧原子和0-2个硫原子并且含有1个或2个芳香环的5-至10-元杂环基,各种情况下其任选被W2所列出的基团一至四取代,
B代表任选被W1所列出的基团一取代或二取代的对-亚苯基,
Z代表氧或硫,
D代表氢,C1-C16-烷基,C2-C16-链烯基,C2-C6-炔基,C1-C16-卤代烷基,C2-C16-卤代链烯基,各自任选被卤素-,C1-C4-烷基-,C2-C4-链烯基-,C2-C4-卤代链烯基-,苯基-,苯乙烯基-,卤代苯基-或卤代苯乙烯基-取代的C3-C8-环烷基或C3-C8-环烷基-C1-C6-烷基,代表各自任选被卤素-或C1-C4-烷基-取代的C5-C8-环烯基或C5-C8-环烯基-C1-C4-烷基,代表各自任选被硝基-,卤素-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C6-卤代烷基-或C1-C6-卤代烷氧基-取代的苯基-C1-C6-烷基,萘基-C1-C6-烷基,四氢萘基-C1-C6-烷基或5-或6-元具有1或2个选自氮,氧和硫的杂原子的杂芳基-C1-C6-烷基,代表-CO-R12,-CO-NR13R14,或者代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
或者
Z和D一起代表任选被硝基-,卤素-,C1-C6-烷基-,C1-C6-烷氧基-,C1-C6-卤代烷基-或C1-C6-卤代烷氧基-取代的苯氧基-C1-C4-烷基,
Y代表直接键,氧,硫,羰基,羰基氧基,氧基羰基,C1-C4-亚烷基,C2-C4-亚烯基,C2-C4-亚炔基,C1-C4-亚烷基氧基,C1-C4-氧基亚烷基,C1-C4-硫代亚烷基,C1-C4-亚烷基二氧基或者代表对亚苯基,其任选被选自W1所列出的基团一取代或二取代,
E代表C1-C16-烷基,C2-C16-链烯基,C2-C6-炔基,C1-C16-卤代烷基,C2-C16-卤代链烯基,任选被卤素-,C1-C4-烷基-,C2-C4-链烯基-,C2-C4-卤代链烯基-,苯基-,苯乙烯基-,卤代苯基-或卤代苯乙烯基-取代的C3-C8-环烷基,代表任选被卤素-或C1-C4-烷基-取代的C5-C8环烯基,代表任选被W1所列出的基团一-至四-取代的苯基,或者代表具有1或2个选自氮,氧和硫的杂原子并且任选被W2所列出的基团一-至四-取代的5-或6-元杂芳基,或者代表基团
-(CH2)p-(CR15R16)q-(CH2)r-G,
R12代表C1-C12-烷基,C1-C12-烷氧基,C2-C12-链烯基,C2-C12-链烯基氧基,各自任选被卤素-,C1-C4-烷基-,C2-C4-链烯基-,C1-C4-卤代烷基-或C2-C4-卤代链烯基-取代的C3-C8-环烷基,C3-C8-环烷基氧基或C3-C8-环烷基-C1-C6-烷基氧基或者代表各自任选被硝基-,卤素-,C1-C12-烷基-,C1-C12-烷氧基-,C1-C12-卤代烷基-或C1-C12-卤代烷氧基-一至四取代的苯基或萘基,
R13代表氢或C1-C12-烷基,
R14代表C1-C12-烷基,C1-C12-卤代烷基,各自任选被卤素-,C1-C4-烷基-,C2-C4-链烯基-,C1-C4-卤代烷基-或C2-C4-卤代链烯基-取代的C3-C8-环烷基,C3-C8-环烷基-C1-C6-烷基或者代表各种情况下任选被卤素-,C1-C12-烷基-,C1-C12-烷氧基-,C1-C12-卤代烷基-或C1-C12-卤代烷氧基-一至四取代的苯基或苯基-C1-C6-烷基,
p,q和r各自独立地代表0,1,2或3,其和小于6,
R15和R16各自独立地代表氢或C1-C4-烷基,
G代表氰基,代表任选被卤素,C1-C4-烷基或C1-C4-卤代烷基一至三取代的,并且在连接点任选被基团R17取代的,具有1-3个相同或不同的选自氮,氧和硫的杂原子的5-或6-元杂环,或者代表下面的基团之一
(a)-CO-R17
(b)-CO-OR18
(c)-CO-NR19R20
(d)-CS-NR19R20
R17代表氢,C1-C6-烷基,C2-C6-链烯基,C1-C4-卤代烷基,C2-C6-卤代链烯基,任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C6-环烷基,或者代表任选被C1-C4-烷基羰基氨基,C1-C4-烷基羰基-C1-C4-烷基氨基和/或选自W3所列出的基团一至五取代的苯基,
R18代表氢,C1-C4-烷基,C2-C6-链烯基,C1-C4-卤代烷基,C2-C6-卤代链烯基,各自任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基或者代表任选被选自W3所列出的基团一至四取代的C6-C10-芳基-C1-C4-烷基,
R19和R20各自独立地代表氢,C1-C4-烷基,C3-C6-链烯基,C1-C4-卤代烷基,C3-C6-卤代链烯基,C1-C4-烷氧基,各自任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,代表苯基或苯基-C1-C4-烷基,其各自任选被选自W3所列出的基团一至五取代,代表-OR18或-NR17R18或者一起代表其中一个亚甲基任选被氧置换的具有4-6个节的亚烷基链,
R21代表-OR18,-NR17R18或者-N(R17)-COOR18,
R22,R23和R24各自独立地代表C1-C6-烷基,
W1代表氢,卤素,氰基,甲酰基,硝基,C1-C6-烷基,三-C1-C4-烷基甲硅烷基,C1-C16-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C2-C6-卤代链烯基氧基,C1-C6-烷基羰基,C1-C16-烷氧羰基,五氟硫基或者-S(O)OOR6,
W2代表卤素,氰基,甲酰基,硝基,C1-C6-烷基,三-C1-C4-烷基甲硅烷基,C1-C16-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C1-C6-烷基羰基,C1-C16-烷氧羰基,五氟硫基,-S(O)OR6或-C(R17)=N-R21,
W3代表卤素,氰基,硝基,C1-C4-烷基,C1-C4-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,二-C1-C4-烷基氨基,-S(O)OR6,-COOR23或-CONR20R27,
R25代表氢,C1-C4-烷基,C1-C4-卤代烷基,任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C7-环烷基或者代表任选被选自W4所列出的基团一至五取代的苯基,
R26和R27各自独立地代表氢,C1-C4-烷基,C3-C6-链烯基,C1-C4-卤代烷基,C3-C6-卤代链烯基,C1-C4-烷氧基,各自任选被卤素-,C1-C4-烷基-或C1-C4-卤代烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,或者代表苯基或苯基-C1-C4-烷基,其各自任选被选自W4所列出的基团一至五取代,代表-OR22或-NR23R24或者一起代表其中一个亚甲基任选被氧置换的具有4-6个节的亚烷基链,
W4代表卤素,氰基,硝基,C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,二-C1-C4-烷基氨基,C1-C6-烷氧基羰基,二-C1-C6-烷基氨基羰基或-S(O)OR6,
条件是所述式(XI)的化合物不包括其中Ar2为下列基团之一的化合物:
并且也不包括以下结构式的化合物:
2.权利要求1的化合物,其中n是1。
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DE19648011A DE19648011A1 (de) | 1996-11-20 | 1996-11-20 | Cyclische Imine |
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-
1996
- 1996-11-20 DE DE19648011A patent/DE19648011A1/de not_active Withdrawn
-
1997
- 1997-11-07 CN CNB971814589A patent/CN1247541C/zh not_active Expired - Fee Related
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Patent Citations (3)
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US3717648A (en) * | 1970-10-21 | 1973-02-20 | Sterling Drug Inc | 1-phenyl-azacarbocyclic-2-imines |
EP0008645A1 (de) * | 1978-08-01 | 1980-03-19 | Schering Aktiengesellschaft | Alkoxyphenylpyrrolidone, Verfahren zu ihrer Herstellung und Arzneimittel auf Basis dieser Verbindungen |
EP0671388A1 (en) * | 1994-03-10 | 1995-09-13 | Hoechst-Roussel Pharmaceuticals Incorporated | (Pyrrolidinyl)phenyl carbamates and intermediate compounds, processes for their preparation and their use as medicaments |
Non-Patent Citations (2)
Title |
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A Liquid Chromatographic Method for Resolving ChiralLactams as Their Diastereomeric Ureide Derivatives. W. H. PIRKLE ET AL.J. ORG. CHEM.,Vol.49 No.13. 1984 * |
DECARBOXYLATION OF PYROGLUTAMIC ACIDS WITHP2O5/CH3SO3H: A GENERAL SYNTHESIS OF5-ARYL-2-PYRROLIDINONES. B. RIGO ET AL.TETRAHEDRON LETT.,Vol.30 No.50. 1989 * |
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