TW200804245A - Amidinylphenyl compounds and their use as fungicides - Google Patents
Amidinylphenyl compounds and their use as fungicides Download PDFInfo
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- TW200804245A TW200804245A TW095139051A TW95139051A TW200804245A TW 200804245 A TW200804245 A TW 200804245A TW 095139051 A TW095139051 A TW 095139051A TW 95139051 A TW95139051 A TW 95139051A TW 200804245 A TW200804245 A TW 200804245A
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- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 239
- 239000000417 fungicide Substances 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 83
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 201000010099 disease Diseases 0.000 claims abstract description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 94
- 241000196324 Embryophyta Species 0.000 claims description 64
- -1 trimethyldecyl Chemical group 0.000 claims description 53
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 42
- 241000221785 Erysiphales Species 0.000 claims description 34
- 230000000855 fungicidal effect Effects 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 17
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- 244000068988 Glycine max Species 0.000 claims description 12
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- 244000000003 plant pathogen Species 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 240000005979 Hordeum vulgare Species 0.000 claims description 11
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
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- 240000006365 Vitis vinifera Species 0.000 claims description 5
- 235000014787 Vitis vinifera Nutrition 0.000 claims description 5
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 5
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- 240000001980 Cucurbita pepo Species 0.000 claims description 4
- 230000002538 fungal effect Effects 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
- 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- 229930182558 Sterol Natural products 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 241001233957 eudicotyledons Species 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 150000003432 sterols Chemical class 0.000 claims description 3
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- 241000233614 Phytophthora Species 0.000 claims description 2
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- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 2
- PZBPHYLKIMOZPR-FIYGWYQWSA-K 2-[4-[2-[[(2r)-1-[[(4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-4-[[(2r,3r)-1,3-dihydroxybutan-2-yl]carbamoyl]-7-[(1r)-1-hydroxyethyl]-16-[(4-hydroxyphenyl)methyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-19-yl] Chemical compound [68Ga+3].C([C@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)NC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1)C1=CC=CC=C1 PZBPHYLKIMOZPR-FIYGWYQWSA-K 0.000 claims 1
- 241001480061 Blumeria graminis Species 0.000 claims 1
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- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
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- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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- 239000010937 tungsten Substances 0.000 claims 1
- 244000000004 fungal plant pathogen Species 0.000 abstract description 8
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 76
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 55
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 22
- 229940125758 compound 15 Drugs 0.000 description 22
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- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 21
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 239000003223 protective agent Substances 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- DDIQWGKUSJOETH-UHFFFAOYSA-N pyrafluprole Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C#N)C(SCF)=C1NCC1=CN=CC=N1 DDIQWGKUSJOETH-UHFFFAOYSA-N 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-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
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- 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
- 235000002020 sage Nutrition 0.000 description 1
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- 239000008159 sesame oil Substances 0.000 description 1
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- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
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- 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
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- 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
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- 229960002317 succinimide Drugs 0.000 description 1
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- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000005936 tau-Fluvalinate Substances 0.000 description 1
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- 229940104261 taurate Drugs 0.000 description 1
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- 235000013616 tea Nutrition 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-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
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 229960004546 thiabendazole Drugs 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
- 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
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-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
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-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
- 229930192474 thiophene Natural products 0.000 description 1
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([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
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 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
- 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
- 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 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
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-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
- 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
- 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
- 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
- 239000002383 tung oil Substances 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 229940005605 valeric acid Drugs 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
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 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
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
200804245 九、發明說明: 【發明所屬之技術領域】 本發明係關於某些甲脑基苯基化合物,其N_氧化物、農 業上適合之鹽及組合物,及其作為殺真菌劑之用途之方法。 【先前技術】 控制由真菌植物病原體引起之植物疾病對於達成高的收 成效率極為重要。植物疾病對觀賞植物、蔬菜、田間作物、 榖類及水果作物之損害可引起生產能力顯著下降,且因此 對消費者而&導致成本提高。雖然出於此目的許多產品可 在市面上購得,但仍繼續需要新的更有效、低成本、低毒 性、環境安全或具有不同作用模式之化合物。 需要之一領域為適用於控制由子囊菌真菌植物病原體引 起之植物疾病(諸如穀類及/或闊葉作物之白粉病)之化合 物。另一需要領域為適用於控制由擔子菌真菌植物病原體 引起之植物疾病(諸如穀類及/或闊葉作物之鏽病)之化合 物。 世界專利申請案公開案WO 2003/093224揭示某些作為新 穎殺真菌活性成分之式i之苯基脒。
R1、R2 ' R3、R4、R5、R6及A被廣泛定義,瓜為❹、i、2 或3 〇 115133.doc 200804245 【發明内容】 所有幾何及立體異構 含有其之農業組合物 本發明係針對式1之化合物(包括 體)、其N-氧化物及農業上適合之鹽, 及其作為殺真菌劑之用途:
其中 …為匕-匕烷基或c3-c4環烷基; R2為cvq烷基; R3 為 Br、C1或 I ; R為C1,或CVC2烷基或CVC2烷氧基,該Ci_c2烷基或
CrC2烷氧基各視情況經一至三個獨立地選自鹵素之 取代基取代; A為C或Si ; R5各自獨立地為視情況經一至三個獨立地選自鹵素之取 代基取代之烷基;且 R5a&H或 CVC2烷基; 其限制條件當A為Si時,則R5a為CrG烷基。 本發明提供控制由子囊菌植物病原體引起之植物疾病 (例如由白粉菌spp·)、葡萄白粉菌 necaiwr)、甜瓜白粉菌⑽)及蘋果白粉菌 /wMirz’c/za)引起之白粉病)及由長螺孢菌 (Helminthosporium)、大麥鐵微病谨(Pyrenophora teres)反大 115133.doc 200804245 麥雲紋病菌seca/b)引起之疾病的方法。此 方法包含將殺真菌有效量之選自式1之化合物、其N_氧化物 及農業上適合之鹽的化合物應用於植物(例如穀類或闊葉 作物)或其部分’或應用於植物種子或幼苗。 本發明亦提供控制由擔子菌植物病原體引起之植物疾病 (例如由柄鑛囷(PMCWa Spp)、咖啡駆孢鏽菌 vaWaihx)、菜豆錄病菌山·、大豆鏽 镜(Phakopsora pachyrhizi)反 1 毐愚鐵儀(Phak〇ps〇ra f、 所ζ·α幻引起之鏽病)之方法。此方法包含將殺真菌有效 量之選自式1之化合物、其N-氧化物及農業上適合之鹽的化 合物應用於植物(例如穀類或闊葉作物)或其部分,或應用於 植物種子或幼苗。 本發明亦提供控制由除子囊菌植物病原體及擔子菌植物 病原體之外之植物病原體(例如半知菌植物病原體)引起之 植物疾病之方法。此方法包含將殺真菌有效量之選自式 化合物、其N-氧化物及農業上適合之鹽的化合物應用於植 物(例如殺類或闊葉作物)或其部分,或應用於植物種子或幼 苗。 【實施方式】 本文所用術語"包含"、"包括"、"具有”或任何其他變體意 欲涵蓋非排他之包括。舉例而t,包含一列要素之組合物: 過程、方法、物品或裝置不必限於彼等要素,而可包括其 他未清楚列出或該組合物、過程、方法、物品或裝置中固 有之要素。此外,除非清楚相反說日月,否貝Γ,或"係指包含 115133.doc 200804245 性或而非排他性或。舉例而言,條件a*b由下列情形中之 任一種滿足:A為真(或存在)且B為假(或不存在),A為假(或 不存在)且B為真(或存在),及A與B均為真(或存在)。 關於要素或組份之實例之數量(亦即具體值),在本發明之 要素或組份前之不定冠詞”一”(a/an)意欲為非限制性的。因 此 應看作包括一個或至少一個,且要素或組份之單數 詞形式亦包括複數,除非該數量明顯意謂單數。舉例而言, 本發明之組合物包含生物學上有效量之,,一,,式丨之化合 物’其應理解為該組合物包含一種或至少一種式1之化合 物。 如本文所提及’單獨或與詞組合使用之術語"幼苗”意謂 自種子之胚胎發育之幼小植物。 如本文所提及,單獨使用或於諸如,,闊葉作物,,之詞中使 用之術語”闊葉’’意謂雙子葉植物,該術語用於描述其特徵 為胚胎具有兩片子葉之被子植物之群。 在以上敍述中,術語”烷基"包括直鏈或支鏈烷基,諸如 曱基、乙基、正丙基、異丙基或不同丁基異構體。"烷氧基,, 包括例如甲氧基及乙氧基。”環烷基”包括例如環丙基及環 丁基。術語”鹵素’’包括氟、氣、溴或峨。在取代基中碳原 子之總數由前綴”CrCj”指示,其中i及j為1至4之數字。舉例 而言,C2烷基表示CH3CH2 ; C3烷基表示例如CH3CH2CH2或 (ch3)2ch。 熟I此項技術者亦將認識到第二胺可形成N -氧化物。製 備第三胺之N·氧化物之合成方法係為熟習此項技術者所極 115133.doc 200804245 為熟知,其包括以過氧酸(諸如過氧乙酸及間氯過苯曱酸 (MCPBA))、過氧化氫、烷基氫過氧化物(諸如第三丁基氫 過氧化物)、過硼酸鈉及雙環氧乙烷(諸如二甲基雙環氧乙 烷)氧化第三胺。此等製備N-氧化物之方法已於文獻中廣泛 描述且回顧,例如參看:T· L. Gilchrist,
Organic 办,第 7卷,第 748-750 頁,S. V· Ley編, Pergamon Press ; M. Tisler及 Β· Stanovnik 5 Comprehensive 少,第三卷,第 1 8-20 頁,A. J· Boulton 及 A. McKillop編,Pergamon Press ; M. R. Grimmett及 B. R. T. Keene,ζ·π ,第 43卷,第 149-161 頁,A· R. Katritzky編,Academic Press ; M. Tisler 及 B. Stanovnik 3 Advances in Heterocyclic Chemistry j 第 9 卷,第 285-291 頁,A. R. Katritzky 及 A. J. Boulton編, Academic Press ;及 G· W. H. Cheeseman及 E. S. G. Werstiuk, Advances in Heterocyclic Chemistry,第 22卷,% 39Q-392 展, A. R. Katritzky及 A. J· Boulton編,Academic Press。 本發明之化合物可作為一或多種立體異構體存在。各種 立體異構體包括對映異構體、非對映體、滞轉異構體及幾 何異構體。熟習此項技術者應瞭解:當一種立體異構體相 對於其他異構體濃度富集.或當將其自其他異構體分離時, 其可更具有活性及/或可展現有益效應。此外,熟習技工瞭 解如何分離、富集及/或選擇性製備該等立體異構體。本發 明之化合物可作為立體異構體之混合物、個別立體異構體 或作為光學活性形式存在。 115133.doc -10- 200804245 熟習此項技術者認則:由於在環境中且在生 下,化合物之鹽與其對應非鹽形式處於平衡中,因此踐丘 有非鹽形式之生物效用。因此,多種以化合物之鹽適:: 控制真菌植物疾病(亦即其為農業上適合的^式丨化合物之 鹽包括與諸如氫漠酸、鹽酸、破酸、麟酸、硫酸、:酸t 丁酸、反丁烯二酸、乳酸”丨頁丁烯二酸、丙二酸、心、 丙酸、水揚酸、酒石酸、4甲贫X旦紗i斗、_ 夂4_甲本石兴酸或戊酸之無機或有機 酸之酸加成鹽。因此,本發明包含選自式化合物、其N· 氧化物及農業上適合之鹽之化合物。 本發明之實施例包括: 實施例A1·其中WaCrC3烷基或CrC4環烷基之式i之化 合物。 實施例A2.其中…為CrC2烧基之實施例A1之化合物。 實施例A3·其中R1為乙基之實施例A2之化合物。 實施例A4·其中112為(:1-(:2烷基之式1之化合物。 實施例A5·其中R2為甲基之實施例A4之化合物。 實施例A6.其中R3為Br或C1之式1之化合物。 實施例A7·其中R3為Br之實施例A6之化合物。 實施例A8.其中R4為C1 ;或其中每一者視情況經一至三個 獨立地選自F及C1之取代基取代烷基或Ci-Cz 烷氧基之式1之化合物。 實施例A9.其中R4為C1;或其中每一者視情況經一至三個 F取代之CrCz烷基或CkQ烷氧基之實施例A8之化合 物0 115133.doc -11 - 200804245 實施例A10·其中R4為其中每一者視情況經一至三個?取 代之q烷基或q烷氧基之實施例八9之化合物。 實施例A11 ·其中R5各自獨立地為視情況經一至三個獨立 地選自F及C1之取代基取代之Ci_C2烷基的式丨之化合 物。 實施例A12.其中R5各自獨立地為視情況經一至三個〇取 代之CrC:2烷基的實施例Ail之化合物。 實施例AU·其中R5各自獨立地為視情況經一至三個〇取 代之Ci烷基的實施例A12之化合物。 貝施例A14·其中A為C且115&為η之式1之化合物。 實施例Β1 ·控制至少一種榖類或闊葉作物中選自由下列 疾病組成之群之植物真菌疾病之方法:由白粉菌、葡 萄白粉菌、甜瓜白粉菌及蘋果白粉菌引起之白粉病; 由長蠕孢菌、大麥網斑病菌及大麥雲紋病菌引起之疾 病;及由柄鏽菌、咖啡駝孢鏽菌、菜豆鏽病菌、大豆 鏽菌及豆薯層鏽菌引起之鏽病,該方法包含將殺真菌 有效畺之選自式1之化合物、其氧化物及農業上適 合之鹽的化合物應用於植物或其部分,或應用於植物 種子或幼苗。 實施例Β2·其中控制至少一種白粉病之實施例以之方法。 實施例Β3 ·其中該植物疾病係由小麥白粉病菌(五〜 f· sp.卜出以·)引起之實施例B2之方法。 實施例B4_其中該植物疾病係由大麥白粉病菌(五〜 gramzWs f. sp· 引起之實施例B2之方法。 115133.doc -12- 200804245 實施例B5 ·其中該植物疾病係由葡萄白粉病菌引起之實 施例B2之方法。 實施例B6.其中該植物疾病係由蘋果白粉菌引起之實施 例B 2之方法。 實施例B 7 ·其中控制至少一種鏽病之實施例b 1之方法。 只施例B8·其中3亥植物疾病係由小麥鐘菌(p此以 引起之實施例Β7之方法。 實施例Β9.其中該植物疾病係由條形柄鐵菌 爪以)引起之實施例B7之方法。 實施例B10·其中該植物疾病係由禾柄鏽菌 gramhh)引起之實施例B7之方法。 貫施例B11 ·其中該植物疾病係由咖啡騎孢鏽菌引起之實 施例B7之方法。 實施例B12·其中該植物疾病係由菜豆鏽病菌引起之實施 例B7之方法。 實施例B13.其中該植物疾病係由豆薯層鏽菌引起之實施 例B7之方法。 實施例B14·其中該植物為雙子葉作物之實施例B1至B13 中任一者之方法。 實施例B15·其中該雙子葉作物係選自大豆、葡萄及葫蘆 之實施例B14之方法。 實施例B16·其中該雙子葉作物為大豆之實施例Bi5之方 法。 實施例B17·其中該雙子葉作物為葡萄之實施例Bi5之方 115133.doc -13· 200804245 法。 實施例B18.其中該雙子葉作物為韻蘆之實施例Bi5之方 法。 實施例A1-A14之組合藉由下列實施例說明: 實施例C 1 ·式1之化合物,其中 R為匕-^烧基或c3-C4環烧基; R2為c「c2烷基; R3為 Br或 C1 ; R為C1 ;或其中每一者視情況經一至三個獨立地選自F 及ci之取代基取代之Cl_C2烷基或氧基;且 R5各自獨立地為視情況經一至三個獨立地選自F及C1 之取代基取代烷基。 實施例C2.實施例C1之化合物,其中 R1為CVC2烷基; R2為甲基; R3 為 Br ; R為Cl ;或其中每一者視情況經一至三個F取代之 CVC2烷基或(VC2烷氧基;且 R5各自獨立地為視情況經一至三個C1取代之Cl_c2烷 基。 應注意其中R4為C1之式1之化合物(例如實施例c 1或實施 例C2之化合物)。 實施例C3·實施例C2之化合物,其中 Ri為乙基; 115133.doc -14- 200804245 r2為甲基; R4為其中每一者視情況經一至三個F取代之Ci烷基或 Ci烷氧基;且 R各自獨立地為視情況經一至三個C1取代之Ci烷基。 實加*例C4.選自由下列各物組成之群之實施例C3的化合 物: ΙνΓ_[2-溴+[(4-甲基戊基)氧基]_5_(三氣甲基)苯基]善乙 基甲基曱醯亞胺醯胺; N’-[2·演_5_甲氧基_4_[3_(三甲基矽烷基)丙氧基]苯基]_尽 乙基]-I甲基甲醯亞胺醯胺; N’-[2-溴-5-(二氟甲氧基)-4-[3兴三甲基矽烷基)丙氧基]苯 基]-Ν-乙基_n_甲基甲醯亞胺醯胺; NL[2H(二氟曱基)_4_[(4_甲基戊基)氧基]苯基]善乙 基甲基甲醯亞胺醯胺;及 Ν^[2-溴-5-甲氧基-4-[(4-曱基戊基)氧基]苯基]·Ν•乙基 甲基甲醯亞胺醯胺。 本發明亦係關於包含殺真菌有效量之本發明之化合物及 界面活丨生 > 彳、固體稀釋劑或液體稀釋劑中之至少一種的殺 真菌組合物。本發明之殺真菌組合物之值得關注的實施例 為彼等包含上述實施例之化合物的實施例。 本發明亦係關於控制由真菌植物病原體引起之植物疾病 之方法,其包含將殺真菌有效量之本發明之化合物(例如作 為本文所述之組合物)應用於植物或其部分或應用於植物 種子。應注意之使用方法為彼等包括上述實施例之化合物 115133.doc -15- 200804245 之方法。 式1之化合物可藉由如流程1 -5所述之下列方法及變體中 之一或多種製備。下式U之化合物中Rl、R2、、r4、r5、 R及A之定義如以上在發明内容中所定義。 如流程1所示,可藉由在諸如二氯甲烷或四氯化碳之惰性 溶劑中使式2之化合物與諸如N-氯代丁二醯亞胺、N_溴代丁 二醯亞胺、N-碘代丁二醯亞胺或其等效物之鹵化劑反應製 備式1之化合物。該反應可在〇至11〇。〇範圍内之溫度下進行 1與48小時之間之時期。隨後使反應混合物達至室溫且將其 過濾。將濾液以稀氫氧化鈉水溶液洗滌,經諸如硫酸鎂之 乾燥劑乾燥且隨後濃縮,得到式丨之化合物。此方法於實例 1之步驟E、實例2之步驟E及實例3之步驟說明。
。多種方法 式2之化合物可如流程2所示自式3之笨胺製備 可用於此轉化。以下五種方法尤其適用。 流程2 R4
2 H5133.doc •16- 200804245 方法1:以其中R6為烷基之式I^I^NCHCOR6:^之縮醛處理 式3之苯胺。此類型之轉化可見於Toste等人,办价仏 1994, 2岑人 1617-1624 中0 方法2 ··在諸如但不限於P0C13或S0C12之鹵化劑存在下以 式HCPC^NR1!^之曱醯胺處理式3之苯胺。此類型之轉化可 見於 Bergman等人,reira/zedro 义 1990,4(5(7 7), 6058_6112 中〇
方法3 :以其中R6為烷基之式HC(OR6)3之原酸酯處理式3 之本胺以形成相應亞胺基鱗’隨後加熱該亞胺基驗與式 hnWr2之胺。此類型之轉化可見於Pissiotas等人之美國專 利 4,209,319 中。 方法4 :以碳醯氯處理式3之苯胺形成異氰酸鹽,隨後使 該異氰酸鹽與式HCpCONR1!^之醯胺反應。此類型之轉化 可見於Charles等人之世界專利申請公開案w〇 2〇〇〇/46184 中〇 方法5:以C2H5〇CH=NCN處理式3之苯胺形成N氰基脒, 隨後使所得N-氰基脒與式HNRlR2之胺反應。此類型轉化可 見於Charles等人之世界專利申請公開案w〇 2〇〇〇/46184 中。此方法於實仓"之步驟咖、實例2之步驟⑽及實例 3之步驟E及F中說明。 式3之化合物可如流程3所示藉由還原式4之化合物中的 石肖基製傷。多種方法可用於此還原。較佳方法包括於濃鹽 酸中之氣化亞錫還原(例如參看乂心.㈤·,1984 卻wmo)、於乙酸及水之料中之鐵粉還原(例如 115133.doc -17- 200804245 參看乂 <9rg· C〜m., 2001,人 4563-4575)、使用氫及諸 如氧化翻(例如參看五容少沖·⑽/⑽广⑽/ < c/zem/wr;;,1991, ηΡλ 359_66)或碳上鈀(例如參看美國專利6,15〇,343)之催 化劑的催化氫化。此方法於實例1之步驟Β、實例2之步驟β 及實例3之步驟D中說明。 流程3
如流程4所說明,式4之化合物可藉由在鹼存在下以式6 之烷基化劑烷基化式5之化合物製備。在式6之烷基化劑 中,X為親核反應離去基團,諸如溴或碘。該反應在至少i 當量之鹼、較佳丨至2當量之鹼存在下進行。適合鹼包括諸 如鹼金屬氫化物(例如氫化鋰、氫化鈉或氫化鉀)、鹼金屬碳 酸鹽或鹼金屬氳氧化物之無機鹼及諸如丨,8_二氮二環 [5.4.0]十一-7-烯之有機鹼。多種溶劑適用於該反應,其包 括例如(但不限於)苯、曱苯、四氫吱嚼、二甲氧基乙烷、乙 腈、N,N__甲基甲醯胺以及此等溶劑之混合物。該反應一 般在、力20與150C之間進行,且較佳在2〇與14〇它之間進 行。反應時間可在1小時至7天之範圍内。 115133.doc -18- 200804245 流程4
其中X為離去基團。 如流程5所示,式4之化合物亦可在鹼存在下自式7之化合 物藉由與式8之適宜醇反應製備。該反應可如下進行··首先 以至少1當篁(較佳1至1·2當量)之驗處理1至2當量(較佳1至 1·4當量)之式8之適宜醇3分鐘至5小時,隨後添加式7之化合 物。適合驗包括諸如驗金屬氫化物(例如氫化叙、氫化納或 氯化鉀)、驗金屬碳酸鹽或鹼金屬氫氧化物之無機鹼,及諸 如丨’8-—氮二環[5·4_0]十一-7-晞之有機驗。諸如氯化四丁基 銨之相轉移試劑可用作反應催化劑。多種溶劑適用於該反 應’諸如苯、甲苯、四氫呋喃、二甲氧基乙烷、乙腈、Ν,Ν_ 一曱基甲醯胺以及此等溶劑之混合物。該反應一般在約_2〇 與150C之間進行,且較佳在2〇與14〇。(:之間進行。反應時 間可在1小時至7天範圍内。流程5之方法之其他實驗細節於 κ例1之步驟Α中說明。 流程5
115133.doc -19- 200804245 或者,式4之化合物亦可自式5之化合物經由Mitsun〇bu反 應製備’其包括使式5之化合物與式8之適宜醇反應。 Mitsunobu反應已為許多回顧之主題。此反應之條件及變 體,參看以下參考文獻以及其中引用之參考文獻·· Hughes, 1992,从 335-656。Mitsunobu反應之其他實驗 細節於實例2之步驟A及實例3之步驟a中說明。 式5、6、7及8之化合物可市面上購得或可由文獻中所教 示之方法或由稍加修改之該等文獻方法製備。 應認識到一些上述用於製備式丨之化合物之試劑及反應 條件可不與存在於中間物中之某些官能基相容。在此等實 例中,將保護/去保護順序或官能基互換併入合成中將有助 於獲得所需產物。保護基團之使用及選擇對熟習化學合成 者顯而易見(例如參看Greene,T. W.; Wuts,P. G. M. Protective Groups in Organic Synthesis ^ f ^ ; Wiley: New York,1991)。熟習此項技術者應認識到,在一些情形下, 在引入如任一個別流程中所述之給定試劑後,進行未詳述 之其他常用合成步驟可為完成式丨之化合物之合成所必 需。熟習此項技術者亦應認識到以不同於所呈示之特定順 序表不之順序執行上述流程所說明之步驟的組合可為製備 式1之化合物所必需。 熟習此項技術者亦應認識到,本文所述式1之化合物及中 間物可經文各種親電子、親核、自由基、有機金屬化、氧 化及還原反應以添加取代基或改質已存在之取代基。 不加進步詳述,咸信使用先前之描述之熟習此項技術 115133.doc 200804245 。因此下列實例應僅視為說明
譜係以PPm四甲基矽烷之低磁場報導,s意謂示單峰,d意謂 雙峰,t意謂三峰,m意謂多峰,br意謂寬單峰。 者可最大程度地利用本發明 性的’而非以無論yf壬你夕士 實例1
製備f[2-漠-4-[(4-甲基戊基)氧基卜5_(三氟甲基)苯基]I 乙基甲基甲醯亞胺醯胺(化合物7) 步驟A :製備1-[(4-甲基戊基)氧基】_4_硝基气三氟甲基)苯 在室溫下於氮下向4-甲基小戊醇(5·85 g, 57·2 mm〇1)於 1,2-二甲氧基乙烷(120 mL)中之溶液逐份添加氫化鈉(於礦 物油中之60%分散液’ 1.96 g,49 mmol)。添加後,在周圍 溫度下將反應混合物攪拌約20分鐘直至氫析出停止。隨後 添加2·氯-5-硝基三氟甲苯(9.93 g,44 mmol)。將反應混合 物加熱至回流且在回流下擾拌隔夜。隨後將混合物冷卻至 室溫,且添加乙酸乙酯(300 mL)。將有機層以鹽水(3 X 200 mL)洗滌,乾燥(MgS04)且濃縮,得到13.5 g呈油狀之粗產 物。使用乙酸乙酯/己烧梯度(1:100至1:20)藉由石夕膠急驟管 柱層析純化粗產物,得到5.67 g呈油狀之標題化合物。 巾 NMR (CDC13) δ 8.5 (d,1H), 8_4 (dd,1H),7.07 (d,1H), 4.16 (t,2H),1.34-1.92 (m,5H),0.93 (d,6H)。 步驟B:製備4-[(4-甲基戊基)氧基]-3-(三氟曱基)苯胺 在氫氣(331 kPa)下於帕爾(Parr)裝置中將1-[(4-甲基戊基) 115133.doc •21- 200804245 氧基]-4-硝基-2-(三氟甲基)苯(亦即步驟A之產物)(3.38 g, 11 ·62 mmol)、氧化翻(〇·8〇 g,3.54 mmol)及無水四氫咬喃(30 mL)之混合物氫化6小時。隨後將反應混合物經由矽藻土過 濾助劑Celite®過濾。隨後將濾液濃縮,得到3 g呈油狀之標 題化合物。 lH NMR (CDC13) δ 6.75-7.92 (m? 3H), 3.93 (t5 2H)? 1.22- 1·82 (m,5H),0.91 (d,6H)。 步驟C :製備N_氰基-N,-[4-(4-甲基戊基)氧基卜3-(三氟甲 基)-苯基】甲醯亞胺醯胺 在室溫下’向N-氰基甲醯亞胺乙酯(1.3 g,13.3 mmol)於 純乙醇(40 mL)中之溶液中逐滴添加4-[(4-曱基戊基)氧 基]三氟曱基)苯胺(亦即步驟B之產物)(3.03 g,11.6 mmol)於純乙醇(4〇 mL)中之溶液。在添加後,在室溫下將 反應混合物攪拌隔夜且隨後濃縮。以20%乙酸乙酯於己烷 (20 mL)中之溶液濕磨殘餘物。藉由過濾收集沉澱物,且將 其經空氣乾燥且隨後在烘箱中乾燥,得到丨·89 g呈白色固體 狀之標題化合物,其在138_14(rc熔融。將濾液濃縮,且將 殘餘物以10%乙酸乙酯於己烷(2〇 mL)中之溶液濕磨。藉由 過渡收集沉澱物,且將其經空氣乾燥且隨後在烘箱中乾 知,又得到0.47 g呈白色固體狀之標題化合物。 H NMR (CDC13) δ 6.9-8.5 (m,5H),4.01 (m,2H),1.82 (m, 2H),1.6 (m,1H),1·35 (m,2H),0.92 (d,6H)。 步驟D :製備N_乙基_N_甲基喟,_[心[(‘甲基戊基)氧 基】-3-(二氟甲基)本基】甲酿亞胺酿胺 115133.doc -22- 200804245 在室溫下向N-氰基-N’-[4-[(4-曱基戊基)氧基]-3-(三氟甲 基)苯基]甲醯亞胺醯胺(亦即步驟C之產物)(2.34 g,7.48 mmol)於乙腈(65 mL)中之混合物中逐滴添加N-乙基甲胺 (3_22 mL,3 7.4 mmol)。在添加後,在室溫下將反應混合物 攪拌隔夜。隨後向反應混合物中添加乙酸乙酯(250 mL)。 將所得混合物以水(200 mL)洗滌,且隨後以鹽水(200 mL) 洗滌。將有機層分離、乾燥(MgS04)且濃縮,得到2.25 g呈 半固體狀之標題化合物。 lH NMR (CDC13) δ 6.78-7.58 (m, 4H)5 3.98 (m5 2H)? 3.2-3.5 (br,2H),3.01 (s,3H),1·78 (m,2H),1·6 (m,1H),1.35 (m, 2H),1.21 (t,3H),0.91 (d,6H) 〇 步称E :製備N,-[2 -溴-4-[(4-甲基戊基)氧基卜5-(三氟甲 基)-苯基】乙基曱基甲醯亞胺醯胺(化合物7) 在室溫下向N-乙基甲基-N’-[4-[(4-甲基戊基)氧 基]-3-(二氟曱基)本基]甲醯亞胺醯胺(亦即步驟d之產 物)(1.3 g,3.94 mmol)於四氯化碳(35 mL)中之溶液中添加
混合物加熱至回流且在回流下攪拌約4小時。隨後將反應混
油狀之標題產物,即本發明之化合物。
2H),3.03 (S,3H),1.8 (m,2H),1.6 (m,1H),135 ),3·2_3·6 (br, 1.35 (m5 2H), 115133.doc -23- 200804245 1.24 (t,3H),0.91 (d,6H) 〇 實例2 製備W-[2-溴-5-甲氧基-4-[3-(三甲基矽烷基)丙氧基]苯 基]乙基]-沁曱基甲醯亞胺醯胺(化合物15) 步驟A :製備[3-(2-甲氧基-4-硝基苯氧基)丙基】三甲基矽烷 在約-10°C下,將偶氮二羧酸二異丙酯(19.6 mL,99.6 mmol)、三苯基膦(28.5 g,109 mmol)及3-(三甲基石夕烧基)-1-丙醇(14.4 mL,91 mmol)添加至4-硝基愈創木酚(15.3 g,91 mmol)於四氫呋喃(400 mL)中之溶液中。隨後將反應混合物 溫至室溫且攪拌隔夜。在減壓下移除過量溶劑,且使用 50-100%於己烷中之1-氯丁烷作為溶離劑藉由矽膠層析純 化殘餘物,得到22 g呈黃色固體狀之標題產物,其在40-43°C 溶融。 咕 NMR (CDC13) δ 7.9 (dd,1H),7.75 (d,1H),6·89 (s,1H),4.06 (t,2H),3·96 (s,3H),1·89 (m,2H),0.6 (m,2H),0.04 (s,9 H)。 步驟B :製備3-甲氧基-4-[3-(三曱基矽烷基)丙氧基]苯胺 在氫氣(331 kPa)下於帕爾(parr)裝置中,將[3-(2-曱氧基-4-硝基苯氧基)丙基]三甲基矽烷(亦即步驟a之產物)(i〇 g, 35.2 mmol)及氧化始(1 g,4.41 mmol)於無水四氫咬喃(25 mL)中之混合物進行氫化7小時。隨後將反應混合物經由矽 藻土過渡助劑Celite®過濾。將濾液濃縮,得到8.6 g呈褐色 油狀之標題化合物。 4 NMR (CDC13) δ 6.71 (d,1H),6.3 (d,1H),6.2 (dd,1H), 3.81-3.9 (m,5H),3.42 (br,2H),1.8 (m,2H),0.58 (m,2H), 115133.doc -24 - 200804245 0.01 (s,9H)。 步驟c :製備N-氰基-N,-[3-甲氧基三甲基矽烷基)丙 氧基]苯基】甲醯亞胺醯胺 在室溫下,向N-氰基曱醢亞胺酯(9·9 g,ίου mm〇i)於 絕對乙醇(50 mL)中之溶液中逐滴添加3-甲氧基_4_[3-(三曱 基石夕烧基)丙氧基]苯胺(亦即步驟B之產物)(8.6 g,33.7 mmol)於絕對乙醇(50 mL)中之溶液。在室溫下將反應混合 物攪拌隔夜及隨後濃縮。以20%乙酸乙酯於己烧中之溶液 濕磨殘餘物。藉由過濾收集沉澱物,且將其經空氣乾燥且 隨後在烘箱中乾燥,得到10 g呈紫色固體狀之粗產物。將 粗產物進一步以10%乙酸乙酯於己烷中之溶液濕磨。藉由 過濾收集沉澱物,將其經空氣乾燥且隨後在烘箱中乾燥, 得到7.8 g呈固體狀之標題化合物,其在142_144^^融。 lU NMR (CDC13) δ 6.6-9.2 (m5 5H), 3.85-4 (m? 5H)5 1.82 (m5 2H),0.58 (m,2H),0.02 (s,9H)。 步驟D :製備N_乙基-N,-[3-甲氧基三甲基矽烷基)丙 氧基】苯基]-N-甲基甲醯亞胺醯胺 將在Fisher-Porter瓶之TV-氰基-#’-[3-甲氧基-4-[3-(三甲基 石夕烧基)丙氧基]苯基]甲醢亞胺醯胺(亦即步驟C之產物)(5 g ’ 16.4 mmol)、TV» 乙基甲胺(7 mL ’ 81.97 mmol)及乙腈(2〇 mL)之混合物在130°C下加熱4小時。將所得混合物冷卻至室 溫且隨後濃縮。使用50-100%於己烷中之乙酸乙酯作為溶離 劑藉由矽膠層析純化殘餘物,得到3 · 1 g呈油狀之標題產物。 iH NMR (CDC13) δ 7.54 (s,1H),6.77 (d,1H),6.58 (d,1H), 115133.doc -25- 200804245 6.42 (dd,1H),3.91 (t,2H),3·85 (s,3H),3.2-3.5 (br,2H), 2.98 (s,3H),1·82 (m,2H),1.2 (t,3H),0.58 (m,2H),0.02 (s, 9H)。 步驟E :製備Nf-[2-演-5-甲氧基-4-[3-(三甲基發烧基)丙氧 基】苯基卜N-乙基]-N-曱基甲醯亞胺醯胺(化合物μ) 在室溫下,向N-乙基-Ν^[3-曱氧基-4-[3-(三甲基矽烷基) 丙氧基]苯基]甲基曱醯亞胺醯胺(亦即步驟d之產物)(1.5 g,4.66 mmol)於四氣化碳(30 mL)中之溶液中添加臭代丁 二醯亞胺(0.91 g,5.12 mmol)。在室溫下將反應混合物攪拌 約3.5小時。隨後將反應混合物濃縮,且使用5〇〇/0於己烧中 之乙S文乙i曰作為》谷離劑精由砍膠層析純化殘餘物,得到 1.42 g呈褐色油狀之標題產物,亦即本發明之化合物。 lK NMR (CDC13) δ 7.27-7.56 (br5 1H)5 7.03 (s, 1H)5 6.46 (s5 1H),3·9 (t,2H),3.84 (s,3H),3.2-3.6 (br,2H),3.02 (s,3H), 1.82 (m,2H),1.23 (t,3H),0.58 (m,2H),0.01 (s,9H)。 實例3 製備N’-[2-溴-5-(二氟甲氧基)-4-[3-(三甲基矽烷基)丙氧基] 苯基]乙基-N-甲基甲醢亞胺醯胺(化合物22) 步驟A :製備5_硝基-2-[3-(三甲基矽烷基)丙氧基】苯甲醛 在-10C下’向偶氮二緩酸二異丙g旨(26 mL,132 mmol) 於無水四氫呋喃(500 mL)中之溶液中添加3-(三曱基矽烷 基)-1-丙醇(19 mL,119.5 mmol)、2-羥基-5-硝基苯甲醛(20 g,119.7 mmol)及三苯基膦(37.7 g,143.3 mmol)。將反應 混合物溫至室溫且攪拌隔夜。隨後在減壓下將反應混合物 115133.doc •26- 200804245 濃縮’且藉由過濾移除所得沉澱物。將濾液濃縮,且使用 10至20%於己烷中之乙酸乙酯作為溶離劑藉由矽膠層析純 化殘餘物,得到12.4 g呈油狀之標題產物。 NMR (CDC13) δ 10.48 (s,1H),8.7 (d,1H),8.4 (dd,1H), 7·09 (d,1H),4.18 (t,2H)5 1·9 (m,2H),0.65 (m,2H),〇·〇5 (s, 9H) 〇 ’ 步驟B:製備5_硝基-2-[3-(三甲基矽烷基)丙氧基】苯酚 在室溫下,向5-硝基_2-[3-(三甲基矽烷基)丙氧基]苯甲醛 (亦即步驟A之產物)(12.4 g,44.3 mmol)於氯仿(120 mL)中 之溶液中添加3-氯過苯甲酸(約53〇/〇純度,ι4· 1 g,531 mmol)。在室溫下將反應混合物攪拌隔夜且隨後過濾。將濾 液以飽和亞硫酸氫鈉水溶液(2x2〇〇mL)洗滌,隨後將其以 飽和碳酸氫鈉水溶液(3 X 200 mL)洗滌、乾燥(MgS04)且濃 縮,得到14 g油。隨後在室溫下將油添加至濃鹽酸(15滴) 於甲醇(60 mL)中之溶液中,且將反應混合物攪拌隔夜。隨 後將反應混合物濃縮,且使用1〇至2〇%於己烷中之乙酸乙 酯作為溶離劑藉由矽膠層析純化殘餘物,得到8·78 g呈油狀 之標題產物。 H NMR (CDC13) δ 7.8-7.84 (m,2H),6.87 (d,1H),5.84 (s, 1H),4.11 (t,2H),1·85 (m,2H),〇·6 (m,2H),0.04 (s,9 H)。 步驟C:製備[3-[2-(二氟甲氧基)-4_靖基苯氧基]丙基】三甲 基矽烷 向5-硝基-2-[3-(二曱基矽烷基)丙氧基]苯酚(亦即步驟B 之產物)(8.77 g,32.6 mmol)於對二噁烷(14〇 mL)中之溶液 中添加溴化四丁基銨(1〇·5 g,32·6 mm〇1)及5〇%氫氧化鈉水 115133.doc -27- 200804245 溶液(28 mL),同時使用丙酮浴將溫度保持在2〇與3〇°C之 間。隨後,經由乾冰冷凝器將Freon® 22(氯二氟曱烷)(43 inL) 添加至反應混合物中。在室溫下,將反應混合物攪拌2小 時’且隨後經由乾冰冷凝器添加額外量之Freon® 22(氯二氟 甲烧)(12 mL)。在室溫下,將反應混合物再攪拌3小時,且 隨後添加二氯甲烷(500 mL)。將反應混合物以水(3 X 300 mL)洗滌、乾燥(MgS04)且濃縮。使用5至10%於己烷中之乙 酸乙酯作為溶離劑藉由矽膠層析純化殘餘物,得到7·26 g 呈油狀之標題產物。 lU NMR (CDCI3) δ 8.05-8.16 (m3 2H), 7 (d5 1H), 6.6 (t, 1H), 4.08 (t,2H),1.85 (m,2H),0.6 (m,2H),0.04 (s,9H)。 步驟D :製備3-(二氟甲氧基)-4-[3-三甲基矽烷基】丙氧基] 苯胺 在氫氣(48 psi,331 kPa)下於帕爾(parr)裝置中將[3-[(2-二氟甲氧基)-4-硝基苯氧基]丙基]三曱基矽烷(亦即步驟C 之產物)(7.24 g,22.7 mmol)、氧化翻(3.58 g,15.76 mmol) 及無水四氫呋喃(70 mL)之混合物氫化隔夜。隨後將反應混 合物經由矽藻土過濾助劑Celite®過濾。將濾液濃縮,得到 6 · 6 g呈褐色油狀之標題化合物。 lK NMR (CDCI3) δ 6.3-7.81 (m? 4H)5 3.87 (t, 2H)5 3.45 (br, 2H),1.77 (m,2H),0.58 (m,2H),0.01 (s,9H)。 步驟E ··製備N-氰基-N’_[3-(二氟曱氧基)-4-[3-(三甲基矽 烧基)-丙氧基】苯基]甲醯亞胺醯胺 在室溫下,向N-氰基甲醯亞胺S旨(2.55 g,26.0 mmol)於 純乙醇(90 mL)中之溶液中逐滴添加3-(二氟甲氧基)-4- 115133.doc -28- 200804245 [3-(三甲基石夕烧基)丙氧基]苯胺(亦即步驟D之產物)(6·58 g,22.8 mmol)於純乙醇(9〇 mL)中之溶液。在添加後,在室 溫下將反應溶液授拌隔夜且隨後濃縮。以2〇%於己烧中之 乙酸乙S旨溶液濕磨殘餘物。藉由過濾收集沉澱物,且將其 經空氣乾燥且隨後在烘箱中乾燥,得到5 g呈固體狀之標題 化合物,其在154-155°C熔融。 lH NMR (CDC13) δ 6.25-8.9 (m5 6H), 3.97 (t? 2H)3 1.8 (m? 2H),0.6 (m,2H),0.03 (s,9H)。 步驟F ··製備(二氟甲氧基)_4_[3_(三甲基矽烷基)丙 氧基]本基]-N -乙基-N-甲基曱酿亞胺酿胺 在室溫下向N-氰基-N’-[3-(二氟甲氧基)_4-[3-(三甲基矽 烧基)丙氧基]苯基]曱醢亞胺醯胺(亦即步驟E之產物)(3.38 g,10 mmol)於乙腈(40 mL)中之懸浮液中逐滴添加义乙基 甲胺(4_3 mL,50 mmol)。在室溫下將所得混合物攪拌隔夜, 且隨後添加乙酸乙酯(200 mL)。將有機溶液以水(2 X 200 mL)洗滌,之後以鹽水(200 mL)洗滌、乾燥(MgS04)且濃縮, 得到3.65 g呈油狀之標題化合物。 lH NMR (CDCI3) δ 7.48 (br5 1H), 6.3-6.9 (m? 4H)5 3.9 (t5 2H),3.2-3.5 (br,2H),2·98 (s,3H),1.78 (m,2H),1.2 (t,3H), 0.58 (m,2H),0·01 (s,9H) 〇 步驟G:製備N’-[2_溴-5·(二氟甲氧基)·4_[3_(三甲基矽烷基) 丙氧基]苯基]乙基甲基甲醯亞胺醯胺(化合 物22) 在室溫下向Ν’-[3-(二氟曱氧基)-‘[3-(三甲基矽烷基)丙 氧基]苯基]乙基甲基曱醯亞胺醯胺(亦即步驟ρ之產 115133.doc -29- 200804245 物)(0.55 g,1.52 mmol)於四氯化碳(7 mL)中之溶液中添加 N-溴代丁二醯亞胺(0.30 g,1.68 mmol)。在添加後,在室溫 下將反應混合物攪拌隔夜且隨後添加二氯甲烷(100 mL)。 將有機混合物以1 N氫氧化鈉水溶液(2 X 100 mL)洗滌、乾 燥(MgS04)且濃縮。使用20%於己烷中之乙酸乙酯作為溶離 劑藉由矽膠層析純化殘餘物,得到0.5 g呈褐色油狀之標題 產物,亦即本發明之化合物。 lH NMR (CDC13) δ 7.27-7.5 (br, 1H)? 7.15 (s? 1H)5 6.7 (s5 1H),6.54 (t,1H),3.9 (t,2H),3.2-3.6 (br,2H),3.02 (s,3H), 1.78 (m,2H),1.23 (t,3H),0.6 (m,2H),0.02 (s,9H)。 藉由本文中所述之程序連同此項技術中已知之方法,可 製備下列表1至6中之化合物。在下表中使用以下縮寫:η意 謂正,i意謂異,c意謂環,OMe意謂甲氧基,OEt意謂乙氧 基。表1至4中之化合物編號係指在索引表A中之化合物。 表1
化合物 編號 R1 R2 R3 R4 化合物 編號 R1 R2 R3 R4 ch3 ch3 Br ch3 C2H5 C2H5 Cl Cl C2H5 ch3 Br ch3 i-C3U7 ch3 Cl Cl C2H5 C2H5 Br ch3 C-C3H5 ch3 Cl Cl /-C3H7 ch3 Br ch3 n-C3H7 ch3 Br CFs C-C3H5 ch3 Br ch3 «-C3H7 ch3 Br ch3 ch3 ch3 Br OMe W-C3H7 ch3 Br ochf2 15 C2H5 ch3 Br OMe /7-C3H7 ch3 Br OMe C2H5 C2H5 Br OMe «-C3H7 ch3 Br Cl 18 /-C3H7 ch3 Br OMe 10 ch3 ch3 Cl cf3 C-C3H5 ch3 Br OMe 3 C2H5 ch3 Cl cf3 115133.doc -30- 200804245 化合物 編號 R1 R2 R3 R4 化合物 編號 R1 R2 R3 R4 ch3 ch3 Br OEt ch3 ch3 Cl OEt 42 c2h5 ch3 Br OEt 43 C2H5 ch3 Cl OEt c2h5 C2H5 Br OEt C2H5 C2H5 Cl OEt W-C3H7 ch3 Br OEt 44 «-C3H7 ch3 Cl OEt /-C3H7 ch3 Br OEt /-C3H7 ch3 Cl OEt C-C3H5 ch3 Br OEt C-C3H5 ch3 Cl OEt ch3 ch3 Br OCHF2 C2H5 C2H5 Cl cf3 22 C2H5 ch3 Br OCHF2 35 /-C3H7 ch3 Cl cf3 C2H5 ch3 Br OCHF2 C-C3H5 ch3 Cl cf3 /-C3H7 ch3 Br OCHF2 ch3 ch3 Cl chf2 C-C3H5 ch3 Br OCHF2 6 C2H5 ch3 Cl chf2 C2H5 ch3 Br C2H5 C2H5 C2H5 Cl chf2 C2H5 ch3 Br CH2CF3 /-C3H7 ch3 Cl chf2 C2H5 ch3 Br CHFCHF2 C-C3H5 ch3 Cl chf2 C2H5 ch3 Br CHCI2 29 ch3 ch3 Br cf3 C2H5 ch3 Br CC13 2 C2H5 ch3 Br cf3 ch3 ch3 Br OCF3 C2H5 C2H5 Br cf3 C2H5 ch3 Br OCF3 34 /-C3H7 ch3 Br cf3 C2H5 C2H5 Br OCF3 C-C3H5 ch3 Br cf3 /-C3H7 ch3 Br OCF3 ch3 ch3 Br chf2 C-C3H5 ch3 Br OCF3 5 C2H5 ch3 Br chf2 ch3 ch3 Cl OMe C2H5 C2H5 Br chf2 16 C2H5 ch3 Cl OMe /-C3H7 ch3 Br chf2 C2H5 C2H5 Cl OMe C-C3H5 ch3 Br chf2 η-Ο,^Άη ch3 Cl OMe «-C3H7 ch3 Br OMe 17 /-C3H7 ch3 Cl OMe C2H5 ch3 I cf3 C-C3H5 ch3 Cl OMe «-C4H9 ch3 Br cf3 C2H5 ch3 I OMe C2H5 ch3 I chf2 C2H5 ch3 I OCF3 «-C4H9 ch3 Br chf2 C2H5 ch3 I ch3 23 C2H5 ch3 Cl ochf2 C2H5 ch3 I OCHF2 «-C4H9 ch3 Br OCHF2 C2H5 ch3 I Cl /-C3H7 ch3 Cl OCHF2 ch3 ch3 Cl Cl C-C3H5 ch3 Cl OCHF2 C2H5 ch3 Cl Cl ch3 ch3 Cl OCHF2 115133.doc -31 - 200804245 表2
R1 化合物 編號 R1 R2 R3 R4 化合物 編號 R1 R2 R3 R4 ch3 ch3 Br ch3 C2H5 C2H5 Cl Cl c2h5 ch3 Br ch3 /-C3H7 ch3 Cl Cl c2h5 C2H5 Br ch3 C-C3H5 ch3 Cl Cl /-C3H7 ch3 Br ch3 W-C3H7 ch3 Br cf3 C-C3H5 ch3 Br ch3 «-C3H7 ch3 Br ch3 ch3 ch3 Br OMe /7-C3H7 ch3 Br ochf2 C2H5 ch3 Br OMe 仏 c3h7 ch3 Br OMe C2H5 C2H5 Br OMe W-C3H7 ch3 Br Cl /-C3H7 ch3 Br OMe ch3 ch3 Cl cf3 C-C3H5 ch3 Br OMe 11 C2H5 ch3 Cl cf3 ch3 ch3 Br OEt ch3 ch3 Cl OEt C2H5 ch3 Br OEt C2H5 ch3 Cl OEt C2H5 C2H5 Br OEt C2H5 C2H5 Cl OEt n-C3H7 ch3 Br OEt «-C3H7 ch3 Cl OEt /-C3H7 ch3 Br OEt /-C3H7 ch3 Cl OEt C-C3H5 ch3 Br OEt C-C3H5 ch3 Cl OEt ch3 ch3 Br OCHF2 C2H5 C2H5 Cl cf3 C2H5 ch3 Br OCHF2 /-C3H7 ch3 Cl cf3 C2H5 ch3 Br OCHF2 C-C3H5 ch3 Cl cf3 /-C3H7 ch3 Br OCHF2 ch3 ch3 Cl chf2 C-C3H5 ch3 Br OCHF2 C2H5 ch3 Cl chf2 C2H5 ch3 Br C2H5 C2H5 C2H5 Cl chf2 C2H5 ch3 Br CH2CF3 Z-C3H7 ch3 Cl chf2 C2H5 ch3 Br CHFCHF2 C-C3H5 ch3 Cl chf2 C2H5 ch3 Br CHCI2 ch3 ch3 Br cf3 C2H5 ch3 Br CC13 12 C2H5 ch3 Br cf3 ch3 ch3 Br OCF3 C2H5 C2H5 Br cf3 C2H5 ch3 Br OCF3 /-C3H7 ch3 Br cf3 115133.doc -32- 200804245 化合物 編號 R1 R2 R3 R4 化合物 編號 R1 R2 R3 R4 c2h5 C2H5 Br OCF3 C-C3H5 ch3 Br cf3 /-C3H7 ch3 Br OCF3 ch3 ch3 Br chf2 C-C3H5 ch3 Br OCF3 C2H5 ch3 Br chf2 ch3 ch3 Cl OMe C2H5 C2H5 Br chf2 C2H5 ch3 Cl OMe Z-C3H7 ch3 Br chf2 C2H5 C2H5 Cl OMe C-C3H5 ch3 Br chf2 n-C3H7 ch3 Cl OMe /7-C3H7 ch3 Br OMe /-C3H7 ch3 Cl OMe C2H5 ch3 I cf3 C-C3H5 ch3 Cl OMe /2-C4H9 ch3 Br cf3 C2H5 gh3 I OMe C2H5 ch3 I chf2 C2H5 ch3 I OCF3 /7-C4H9 ch3 Br chf2 C2H3 ch3 I ch3 C2H5 ch3 Cl OCHF2 C2H5 ch3 I OCHF2 λ?-〇4Η9 ch3 Br OCHF2 C2H5 ch3 I Cl z,C3H7 ch3 Cl OCHF2 ch3 ch3 Cl Cl C-C3H5 ch3 Cl OCHF2 C2H5 ch3 Cl Cl ch3 ch3 Cl OCHF2 表3 钱Λ
化合物 編號 R2 R1 R3 R4 化合物 編號 R2 R1 R3 R4 ch3 ch3 Br ch3 C2H5 C2H5 Cl Cl C2H5 ch3 Br ch3 /-C3H7 ch3 Cl Cl C2H5 C2H5 Br ch3 C-C3H5 ch3 Cl Cl /-C3H7 ch3 Br ch3 W-C3H7 ch3 Br cf3 C-C3H5 ch3 Br ch3 W-C3H7 CH3 Br ch3 CH3 ch3 Br OMe /7-C3H7 CH3 Br ochf2 25 C2H5 ch3 Br OMe CH3 Br OMe C2H5 C2H5 Br OMe /7-C3H7 ch3 Br Cl 30 /-C3H7 ch3 Br OMe ch3 ch3 Cl cf3 C-C3H5 ch3 Br OMe 4 C2H5 ch3 Cl cf3 ch3 ch3 Br OEt ch3 CH3 Cl OEt 115133.doc -33- 200804245 化合物 編號 R2 R1 R3 R4 化合物 編號 R2 R1 R3 R4 36 c2h5 ch3 Br OEt 37 C2H5 ch3 Cl OEt C2H5 C2H5 Br OEt C2H5 C2H5 Cl OEt 38 «-C3H7 ch3 Br OEt 39 ch3 Cl OEt 40 /-C3H7 ch3 Br OEt 41 /-C3H7 ch3 Cl OEt C-C3H5 ch3 Br OEt C-C3H5 ch3 Cl OEt ch3 ch3 Br OCHF2 C2H5 C2H5 Cl cf3 C2H5 ch3 Br OCHF2 /-C3H7 ch3 Cl cf3 27 C2H5 ch3 Br OCHF2 C-C3H5 ch3 Cl cf3 Z-C3H7 ch3 Br OCHF2 ch3 ch3 Cl chf2 C-C3H5 ch3 Br OCHF2 9 C2H5 ch3 Cl chf2 C2H5 ch3 Br C2H5 C2H5 C2H5 Cl chf2 C2H5 ch3 Br CH2CF3 /-C3H7 ch3 Cl chf2 C2H5 ch3 Br CHFCHF2 C-C3H5 ch3 Cl chf2 C2H5 ch3 Br CHCI2 ch3 ch3 Br cf3 C2H5 ch3 Br CC13 7 C2H5 ch3 Br cf3 ch3 ch3 Br OCF3 C2H5 C2H5 Br cf3 C2H5 ch3 Br OCF3 /-C3H7 ch3 Br cf3 C2H5 C2H5 Br OCF3 C-C3H5 ch3 Br cf3 Z-C3H7 ch3 Br OCF3 ch3 ch3 Br chf2 C-C3H5 ch3 Br OCF3 8 C2H5 ch3 Br chf2 ch3 ch3 Cl OMe C2H5 C2H5 Br chf2 26 C2H5 ch3 Cl OMe /-C3H7 ch3 Br chf2 C2H5 C2H5 Cl OMe C-C3H5 ch3 Br chf2 33 «-C3H7 ch3 Cl OMe 31 τι^^Άη ch3 Br OMe 32 /-C3H7 ch3 Cl OMe c2h5 ch3 I CF3 C-C3H5 ch3 Cl OMe W-C4H9 CHb Br cf3 C2H5 ch3 I OMe C2H5 ch3 I chf2 C2H5 ch3 I OCF3 W-C4H9 ch3 Br chf2 C2H5 ch3 I ch3 28 C2H5 ch3 Cl ochf2 C2H5 CHb I OCHF2 W-C4H9 ch3 Br OCHF2 C2H5 ch3 I Cl /-C3H7 ch3 Cl OCHF2 1 ch3 ch3 Cl Cl C-C3H5 ch3 Cl OCHF2 C2H5 ch3 Cl Cl ch3 ch3 Cl OCHF2 115133.doc -34- 200804245 表4
化合物 編號 R1 R2 R3 R4 化合物 編號 R1 R2 R3 R4 ch3 ch3 Br ch3 C2H5 C2H5 Cl Cl C2H5 ch3 Br ch3 /-C3H7 ch3 Cl Cl C2H5 C2H5 Br ch3 C-C3H5 ch3 Cl Cl /-C3H7 ch3 Br ch3 /7-C3H7 ch3 Br cf3 C-C3H5 ch3 Br ch3 /1-C3H7 ch3 Br ch3 ch3 ch3 Br OMe ch3 Br ochf2 24 C2H5 ch3 Br OMe W-C3H7 ch3 Br OMe C2H5 C2H5 Br OMe /7-C3H7 ch3 Br Cl 1-C3H7 ch3 Br OMe ch3 ch3 Cl cf3 C-C3H5 ch3 Br OMe 13 C2H5 ch3 Cl cf3 ch3 ch3 Br OEt ch3 ch3 Cl OEt C2H5 ch3 Br OEt C2H5 ch3 Cl OEt C2H5 C2H5 Br OEt C2H5 C2H5 Cl OEt /7-C3H7 ch3 Br OEt W-C3H7 ch3 Cl OEt 1-C3H7 ch3 Br OEt /-C3H7 ch3 Cl OEt C-C3H5 ch3 Br OEt C-C3H5 ch3 Cl OEt ch3 ch3 Br OCHF2 C2H5 C2H5 Cl cf3 C2H5 ch3 Br OCHF2 /-C3H7 CH3 Cl cf3 C2H5 ch3 Br OCHF2 C-C3H5 ch3 Cl cf3 /-C3H7 ch3 Br OCHF2 ch3 ch3 Cl chf2 C-C3H5 ch3 Br OCHF2 19 C2H5 ch3 Cl chf2 C2H5 ch3 Br C2H5 C2H5 C2H5 Cl chf2 C2H5 ch3 Br CH2CF3 /-C3H7 ch3 Cl chf2 C2H5 ch3 Br CHFCHF2 C-C3H5 ch3 Cl chf2 C2H5 ch3 Br CHCh ch3 ch3 Br cf3 C2H5 ch3 Br ccl3 14 C2H5 ch3 Br cf3 ch3 ch3 Br OCF3 C2H5 C2H5 Br cf3 C2H5 ch3 Br OCF3 /-C3H7 ch3 Br cf3 C2H5 C2H5 Br OCF3 C-C3H5 ch3 Br cf3 115133.doc -35- 200804245 化合物 編號 R1 R2 R3 R4 化合物 編號 R1 R2 R3 R4 /-c3h7 ch3 Br OCF3 ch3 ch3 Br chf2 c-C3H5 ch3 Br OCF3 20 C2H5 ch3 Br chf2 ch3 ch3 Cl QMe C2H5 C2H5 Br chf2 21 C2H5 ch3 Cl OMe /-C3H7 ch3 Br chf2 C2H5 C2H5 Cl OMe C-C3H5 ch3 Br chf2 /7-C3H7 ch3 Cl OMe /7-C3H7 ch3 Br OMe /-C3H7 ch3 Cl OMe C2H5 ch3 I cf3 C-C3H5 ch3 Cl OMe /7-C4H9 ch3 Br cf3 C2H5 ch3 I OMe C2H5 ch3 I chf2 C2H5 ch3 I OCF3 ch3 Br chf2 C2H5 ch3 I ch3 C2H5 ch3 Cl OCHF2 C2H5 ch3 I OCHF2 ^7-〇4Η9 ch3 Br OCHF2 C2H5 ch3 I Cl z-C3H7 ch3 Cl OCHF2 ch3 ch3 Cl Cl C-C3H5 ch3 Cl OCHF2 C2H5 ch3 Cl Cl ch3 ch3 Cl OCHF2 表5 Λ
Έ? R2 R1 R2 R3 R4 R1 R2 R3 R4 ch3 ch3 Br ch3 C2H5 C2H5 Cl Cl C2H5 ch3 Br ch3 i-C3H7 ch3 Cl Cl C2H5 C2H5 Br ch3 C-C3H5 ch3 Cl Cl Z-C3H7 ch3 Br ch3 Π-ΟβΗγ ch3 Br cf3 C-C3H5 ch3 Br ch3 «-c3h7 ch3 Br ch3 ch3 ch3 Br OMe n-C3H7 ch3 Br ochf2 C2H5 ch3 Br OMe W-C3H7 ch3 Br OMe C2H5 C2H5 Br OMe «-C3H7 ch3 Br Cl /-C3H7 ch3 Br OMe ch3 ch3 Cl cf3 C-C3H5 ch3 Br OMe C2H5 ch3 Cl cf3 ch3 ch3 Br OEt ch3 ch3 Cl OEt C2H5 ch3 Br OEt C2H5 ch3 Cl OEt 115133.doc -36- 200804245 R1 R2 R3 R4 R1 R2 R3 R4 C2H5 C2H5 Br OEt C2H5 C2H5 Cl OEt /7-C3H7 ch3 Br OEt M-C3H7 ch3 Cl OEt /-C3H7 ch3 Br OEt /-C3H7 ch3 Cl- OEt C-C3H5 ch3 Br OEt C-C3H5 ch3 C1 OEt ch3 ch3 Br OCHF2 C2H5 C2H5 Cl cf3 C2H5 ch3 Br OCHF2 /-C3H7 ch3 Cl cf3 C2H5 ch3 Br OCHF2 C-C3H5 ch3 Cl cf3 /-C3H7 ch3 Br OCHF2 ch3 ch3 Cl chf2 C-C3H5 ch3 Br OCHF2 C2H5 ch3 Cl chf2 C2H5 ch3 Br C2H5 C2H5 C2H5 Cl chf2 C2H5 ch3 Br CH2CF3 Z-C3H7 ch3 Cl chf2 C2H5 ch3 Br CHFCHF2 C-C3H5 ch3 Cl chf2 C2H5 ch3 Br CHCI2 ch3 ch3 Br cf3 C2H5 ch3 Br CC13 C2H5 ch3 Br cf3 ch3 ch3 Br OCF3 C2H5 C2H5 Br cf3 C2H5 ch3 Br OCF3 /•-C3H7 ch3 Br cf3 C2H5 C2H5 Br 〇CF3 C-C3H5 ch3 Br cf3 /-C3H7 ch3 Br OCF3 ch3 ch3 Br chf2 C-C3H5 ch3 Br OCF3 C2H5 ch3 Br chf2 ch3 ch3 Cl Ome C2H5 C2H5 Br chf2 C2H5 ch3 Cl Ome /-C3H7 ch3 Br chf2 C2H5 C2H5 Cl Ome C-C3H5 ch3 Br chf2 ch3 Cl Ome «-C3H7 ch3 Br OMe /-c3h7 ch3 Cl Ome C2H5 CHb I cf3 C-C3H5 ch3 Cl Ome ^2-〇4Η9 ch3 Br cf3 C2H5 ch3 I Ome c2h5 ch3 I chf2 C2H5 ch3 I OCF3 /7-C4H9 ch3 Br chf2 C2H5 ch3 I ch3 C2H5 ch3 Cl OCHF2 C2H5 ch3 I OCHF2 ^-C4H9 ch3 Br OCHF2 C2H5 ch3 I Cl /-C3H7 ch3 Cl OCHF2 ch3 ch3 Cl Cl C-C3H5 ch3 Cl OCHF2 C2H5 ch3 Cl Cl ch3 ch3 Cl OCHF2 115133.doc -37- 200804245 表6 R4
(R5a) (R5)2A R3 R4 BrCH2(CH3)2Si Br cf3 FCH2(CH3)2Si Br cf3 ICH2(CH3)2Si Br cf3 BrCH2(CH3)2Si Br chf2 FCH2(CH3)2Si Br chf2 ICH2(CH3)2Si Br chf2 C2H5(CH3)2Si Br cf3 (ClCH2)2(CH3)Si Br cf3 (C2H5)2(CH3)Si Br cf3 BrCH2(CH3)2Si Cl cf3 ICH2(CH3)2Si Br Cl BrCH2(CH3)2Si Br Cl FCH2(CH3)2Si Br Cl BrCH2(CH3)2Si Br och3 BrCH2(CH3)2Si Cl och3 C2H5(CH3)2Si Br och3 (C2H5)2(CH3)Si Br och3 C2H5(CH3)2Si Br ochf2 ICH2(CH3)2Si Br ochf2 BrCH2(CH3)2Si Br ochf2 FCH2(CH3)2Si Br ochf2 BrCH2(CH3)2Si Cl ochf2 (CH3)2CH Br ch2f (ch3)3c Br ch2f (CH3)3Si Br ch2f (CH3)2CH Cl ch2f ClCH2(CH3)2Si Br ch2f (CH3)3C Cl ch2f (CH3)3Si Cl ch2f (ClCH2)2(CH3)Si Cl ch2f 115133.doc -38- 200804245 調配物/效用 本發明之化合物一般用作包含液體稀釋劑、固體稀釋劑 或界面活性劑中之至少一者之與農業上適合之載劑的調配 物或,且&物。调配物或組合物成分經選擇以與活性成分之 物理特性、應用模式及諸如土壤類型、濕度及温度之環境 因=相-致。適用調配物包括諸如溶液之液體(包括可乳化 之濃縮物)、m乳液(包括微乳液及/㈣浮乳液)及視 需要可稠化成凝膠之類似物。適用調配物進一步包括固 體’諸如粉塵、粉末、顆粒、球粒、鍵齊!、膜(包括種衣), 及可為水中可分散(可濕性)或水中可溶之類似物。活性成分 可、工(微)膠囊化且進一步形成為懸浮液或固體調配物;或者 全部活性成分之調配物可經朦囊化(或"經包衣")。膠囊化可 控制或延遲活性成分之釋放。可噴霧之調配物可在適合介 質中擴展且以每公頃約—至㈣公升之喷霧體積使用。高 濃度組合物主要用作用於進—步調配之中間物。 調配物通常含有下列近似範圍内之有效量之活性成分、 稀釋劑及界面活性劑,其合計達1〇〇重量%。 重量% 沽性 ________ 稀釋劑 界面活性劑 u.uu i-y〇 0-99.999 0-15 1-50 40-99 0-50 1-25 70-99 0-5 0.001-99 5-99.999 0-15 90-99 0-10 0-2 水中可分散及水中可溶 之顆粒、錠劑及粉末 懸浮液、乳液、溶液 (包括可乳化之濃縮物) 粉塵 顆粒及球粒 高濃度組合物 115133.doc -39- 200804245 典型固體稀釋劑於Watkins等人,/ί⑽<9//似ecizWA Dust Diluents and Carriers,第二版,Dorland Books, Caldwell,New Jersey中描述。典型液體稀釋劑於Marsden, 心以⑼仏 ,第二版,Interscience,New York,1950·
McCutcheon rs Detergents and Emulsifiers Annual, Allured Publ. Corp·,Ridgewood,New Jersey 以及 Sisely 及 Wood,
Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc·,New York,1964中描述,其列出界面活性劑及推薦之 用途。所有調配物可含有微量添加劑以減少泡沫、結塊、 腐蝕、微生物生長及類似情形,或可含有稠化劑以增加黏 度。 界面活性劑包括例如聚乙氧基化醇、聚乙氧基化烷基 酚、聚乙氧基化脫水山梨糖醇脂肪酸酯、磺基丁二酸二烷 基酯、硫酸烷基酯、烷基苯磺酸鹽、有機聚矽氧、N,N-二 烷基牛磺酸酯、木質素磺酸鹽、萘磺酸鹽甲醛縮合物、聚 羧酸酯、甘油酯、聚氧乙烯/聚氧丙烯嵌段共聚物及烷基多 醣苷(其中稱為聚合度(D.P.)之葡萄糖單元之數目可在1至3 範圍内且烧基單元可在(1!6至C14範圍内)(參看尸wre 办77"以72, 125 5-1264)。固體稀釋劑包括例如諸 如膨潤土、蒙脫石、綠坡縷石及高嶺土之黏土、澱粉、糖、 石夕石、滑石、石夕藻土、尿素、礙酸#5、碳酸納及碳酸氫納 及硫酸鈉。液體稀釋劑包括例如水、N,N-二甲基甲贐胺、 二甲亞職、N-烧基咕洛咬酮、乙二醇、聚丙二醇、破酸丙 一 S旨、-一 7G S旨、石堪、烧基苯、烧基蔡、甘油、三乙酸甘 115133.doc •40- 200804245 油酉曰、橄欖油、蓖麻油、亞麻子油、桐油、芝麻油、玉米 油、化生油、棉花籽油、大豆油、油菜籽油及椰子油、脂 肪S欠S曰諸如環己酮、2-庚酮、異佛爾酮及4-羥基-4-曱基 -2-戊酮之_、諸如乙酸己酯、乙酸庚酯及乙酸辛酯之乙酸 酯,及諸如甲醇、環己醇、癸醇、苄醇及四氫糠醇之醇。 本發明之適用調配物亦可含有熟習此項技術者熟知之物 質作為調配助劑,例如消泡劑、成膜劑及染料。消泡劑可 匕括水中了为散之液體’其包含如Rho dor si 1® 416之聚有機 矽氧烷。成膜劑可包括聚乙酸乙烯酯、聚乙酸乙烯酯共聚 物、聚乙烯吡咯啶酮_乙酸乙烯酯共聚物、聚乙烯醇、聚乙 稀醇共聚物及蠟。染料可包括水中可分散之液體著色劑組 合物,如Pro_lzed⑧Colorant Red。熟習此項技術者應瞭解, 其為調配助劑之非詳盡清單。調配助劑之適合實例包括彼 等本文中所列出之助劑及彼等列於由MC Publishing
Company出版之McCutcheon’s 2001,Volume 2 : Functional Materials及PCT公開案WO 03/024222中之助劑。 包括可乳化濃縮物之溶液可藉由簡單混合該等成分製 備。粉塵及粉末可藉由摻混及通常如在錘磨機或流體能磨 機中研磨製備。懸浮液通常藉由濕磨製備,例如參看U. S. 3,060,084。顆粒及球粒可藉由將活性成分噴灑於預成型之 顆粒載體上或藉由聚結技術製備。參看Browning, ’Agglomeration' Chemical Engineering, December 4, 1967 ’ 第 147-4 名夏,Perry fs Chemical Engineer’s Handbook, 第四版,McGraw,Hill,New York,1963,第 8-57頁及其後頁, 115133.doc -41- 200804245 及WO 91/13546中。球粒可如U.S· 4,172,714中所述製備。 水分散性及水溶解性之顆粒可如U.S· 4,144,050、U.S. 3,920,442及DE 3,246,493中之教示製備。錠劑可如U.S. 5,180,5 87、U.S. 5,232,701 及 U.S. 5,208,030 中之教示製備。 膜可如GB 2,095,5 5 8及U.S. 3,299,566中之教示製備。 關於調配技術之其他資訊,參看T_ S. Woods,"The Formulator’s Toolbox - Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks及 T. R. Roberts編, Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999,第 120-133 頁。亦參看11.8.3,23 5,361,第6欄第16列 至第7欄第19列及實例10-41 ; U.S· 3,309,192,第5欄第43 列至第7欄第62列及實例8、12、15、39、41、52、53、58、 132、138-140、162-164、166、167 及 169-182 ; U.S· 2,891,855,第3欄第66列至第5欄第17列及實例1-4 ; Klingman,Weed Control as a Science, John Wiley and Sons, Inc.5 New York, 1961 ^ % 81-96K » Hance^ K » Weed Control Handbook^ % 8j{£ 5 Blackwell Scientific Publications, Oxford, 1989 ; Sl Developments in formulation technology, PJB Publications,Richmond,UK,2000 o 在下列實例中,所有百分比均以重量計且所有調配物以 習知方式製備。化合物編號係指索引表A中之化合物。 115133.doc -42- 200804245
實例A 高濃度濃縮物 化合物7 98.5% 二氧化矽氣溶膠 0.5% 合成非晶形精細二氧化矽 1.0%。 實例B 可潤濕粉末 化合物7 65.0% 十二烷基苯酚聚乙二醇醚 2.0% 木質素磺酸鈉 4.0% 矽鋁酸鈉 6.0% 蒙脫石(經煅燒) 23.0% 〇 實例C 顆粒 化合物7 10.0% 綠坡縷石顆粒(低揮發性物質, 0.71/0.30 mm ; U.S.S.第 25-50 號篩) 90.0% 〇 實例D 水性懸浮液 化合物7 25.0% 水合綠坡縷石 3.0% 粗木質素磺酸鈣 10.0% 填酸二氫鈉 0.5% 水 61.5%。 115133.doc -43- 200804245 實例E 25.0% 10.0% 5.0% 1.0% 5 9 · 0 % 〇 實例F 1.0% 30.0% 30.0% 19.0% 20.0% 〇 擠出球粒 化合物7 無水硫酸鈉 粗木質素磺酸妈 烷基萘磺酸鈉 鈣/鎂膨潤土 微乳液 化合物7 三乙酸甘油酉旨 C8-C10烷基多醣: 單油酸甘油酯 水 本發明化合物適用作植物疾病控制劑。因此本發明進一 步係關於用於控制由植物病原體引起之植物疾病之方法, 該方法包含將有效量之本發明化合物或含有該化合物之殺 真菌組合物應用於欲保護之植物或其部分,或應用於欲保 護之植物種子或幼苗。 由於式1化合物之相對低之植物毒性,因此認為其尤其有 利於用於雙子葉(例如闊葉)植物上。因此,式i化合物對雙 子葉植物可用以提供有效真菌疾病控制。 式1之化合物及其殺真菌組合物適用於控制真菌植物疾 病,諸如白粉病及鏽病,該等疾病由子囊菌、擔子菌及半 115133.doc -44- 200804245 知菌類中之真菌植物病原體引起,且折磨廣泛種類之觀賞 植物、蔬菜、田間作物、榖類及水果作物。此等病原體包 括: 子囊函’其包括由白粉菌spp·)(包括小麥白粉病 _、大麥白氣病囷及蓼白粉菌(五、葡萄白 粉菌、甜瓜白粉菌及蘋果白粉菌引起之榖類及闊葉作物之 白粉病及由諸如小麥褐斑長蠕孢菌(价〜加〜印奶·謂 raw山)、大麥網斑病菌及大麥雲紋病菌之長蠕孢菌 (i/e/mhi/zoMorkm spp·)引起之疾病; 擔子菌,其包括由柄鏽菌(諸如小麥鏽菌、條形柄鏽菌、大 麥柄鏽菌、禾柄鏽菌及花生鏽菌(i^ccz>n.a arac/nWb))、咖啡駝孢鏽菌、菜豆鏽病菌、大豆鏽菌及豆薯 層鏽菌引起之穀類與闊葉作物之鏽病; 及其他與該等病原體相關之屬及種,其包括彼等歸類於半 知菌之病原體。 應注意本發明之化合物控制由白粉菌科 真菌(例如白粉菌(五sp·))引起之白粉病的用途。亦應 注意本發明之化合物控制由柄鏽菌科(户此以⑴·此⑽勾真菌 (例如柄鏽菌引起之鏽病。 式1之化合物可用於控制廣泛種類之經濟植物之真菌疾 病,諸如苜蓿、大麥、棉花、小麥、油菜、甜菜、玉米;、、 π木、大旦、稻、燕麥、花生、蔬菜(包括萵苣、根甜菜、 豌豆、豆、胡蘿葡、油菜作物、萌產作物、番蘇及胡椒、、 馬鈐薯)、多年生栽種作物(包括咖啡'可可、油掠搁、橡膠、 115133.doc -45- 200804245 甘蔗、葡萄、柑橘(例如橙、橘子、檸檬、酸橙、葡萄柚)、 蘋果、櫻桃、梨、桃、杏及其他水果樹、堅果樹、香蒸、 車前草、鳳梨、蛇麻子、茶)及諸如桉樹及針葉樹(例如火炬 松)之林木,及草皮類(例如肯塔基藍草(Kentucky blnegrass)、聖奥古斯丁草(St· Augustine grass)、肯塔基牛 毛草(Kentucky fescue)及百慕大草(Bermuda grass))。尤其應 注意式1之化合物用於控制下列雙子葉作物中之真菌疾病 之效用:大豆、葡萄及葫蘆。 亦可將本發明之化合物與一或多種其他殺蟲劑、殺真菌 劑、殺線蟲劑、殺菌劑、殺蟎劑、生長調節劑、化學滅菌 劑、化學信息素、驅避劑、引誘劑、信息素、取食刺激劑 或其他生物活性化合物混合以形成產生甚至更廣泛之農業 保護範圍之多組份殺蟲劑。可與本發明之化合物調配之此 等農業保護劑之實例為:殺蟲劑,諸如阿巴汀(abamectin)、 乙醢甲胺石粦、榖硫鱗(azinphos_methyl)、畢芬寧 (bifenthrin)、3_溴 _1-(3_氣-2-吡啶基)·Ν_[4-氰基-2-甲基-6-[(曱基胺基)羰基]笨基]-1Η- u比唑_5_羧醯胺、布芬淨 (buprofezin)、加保扶(carbofuran)、克芬那比 (chlorfenapyr)、克川利普樂(chlorantraniliprole)、毒死碑 (chlorpyrifos)、曱基毒死碑(chlorpyrifos-methyl)、西福托 芬(cyflumetofen)、西福寧(cyfluthrin)、β-西福寧、賽洛寧 (cyhalothrin)、λ-賽洛寧、第滅寧(deltamethrin)、戴芬西隆 (diafenthiuron)、二嗪農(diazinon)、二福隆(diflubenzuron)、 四氟甲醚菊醋(dimefluthrin)、樂果(dimethoate)、達特南 115133.doc -46 - 200804245 (dinotefuran)、伊芬化利(esfenvalerate)、雙氧威 (fenoxycarb)、芬普寧(fenpropathrin)、芬 4匕辛J (fenvalerate)、 費普尼(fipronil)、氟咬蟲醯胺(flonicamid)、氟苯二醯胺 (flubendiamide)、護賽寧(flucythrinate)、氟胺氰菊酯 (tau-fluvalinate)、豐福斯(fonophos)、益達胺 (imidacloprid)、茚蟲威(indoxacarb)、異柳磷(isofenphos)、 馬拉硫鱗(malathion)、美它福米作(metaflumizone)、聚乙 酸、曱胺填、殺撲鱗(methidathion)、納乃得(methomyl)、 美賜年(methoprene)、曱氧滴滴洋(methoxychlor)、甲氧节 氟菊酉旨(metofluthrin)、亞素靈(monocrotophos)、諸福慕容 (noviflumuron)、歐殺滅(oxamyl)、對石荒石粦(parathion)、曱基 對硫構(parathion-methyl)、賽滅寧(permethrin)、福瑞松 (phorate)、裕必松(phosalone)、益滅松(phosmet)、構胺 (phosphamidon)、比力口普(pirimicarb)、佈飛松(profenofos)、 普福林(profluthrin)、普福普樂(pyrafluprole)、唆蟲丙醚 (pyridalyl)、普瑞福昆贊(pyrifluquinazon)、普瑞普樂 (pyriprole)、魚藤酮(rotenone)、螺二克芬(spirodiclofen)、 螺曱虫茜酉旨(spiromesifen)、皮若特麥(spirotetramat)、硫丙填 (sulprofos)、得布芬載(tebufenozide)、特飛林(tefiuthrin)、 託福松(terbufos)、殺蟲畏(tetrachlorvinphos)、σ塞蟲嗓 (thiamethoxam)、硫地克(thiodicarb)、泰滅寧 (tralomethrin)、三氯填酸 S旨(trichlorfon)及殺蟲隆 (triflumuron); 殺真菌劑,諸如酸化苯幷σ塞二嗤 (acibenzolar)、 阿迪嗎淋(aldimorph) 、σ坐石黃菌胺 115133.doc •47- 200804245 (amisulbrom)、氧環唆(azaconazole)、亞托敏 (azoxystrobin)、苯霜靈(benalaxyl)、免賴得(benomyl)、苯 口塞瓦利(benthiavalicarb)、異丙基苯嘆瓦利(benthiavalicarb-isopropyl)、比謹密(binomial)、聯苯、比多農(bitertanol)、 殺稻瘦菌素_S(blasticidin_S)、紫紅混合物(Bordeaux mixture)(三元硫酸銅)、博克利(boscalid)/尼枯彼芬 (nicobifen)、糠菌嗤(bromuconazole)、乙。密紛磧酸酉旨 (bupirimate)、丁賽特(buthiobate)、萎鐵靈(carboxin)、加普 胺(carpropamid)、四氯丹(captafol)、蓋普丹(captan)、貝芬 替(carbendazim)、地茂丹(chloroneb)、四氣異苯腈 (chlorothalonil)、乙菌利(chlozolinate)、克黴唾 (clotrimazole)、氯氧化銅、諸如硫酸及氫氧化銅之銅鹽、 賽座滅(cyazofamid)、嗟芬胺(cyflufenamid)、霜脲氰 (cymoxanil)、環克座(cyproconazole)、鳴菌環胺(cyprodinil)、 益發靈(dichlofluanid)、二氣西莫(diclocymet)、二氯美 (diclomezme)、氯石肖胺(dicloran)、乙黴威(diethofencarb)、 苯醚甲環嗤(difenoconazole)、達滅芬(dimethomorph)、醚菌 胺(dimoxystrobin)、達克利(diniconazole)、達克利-Μ (diniconazole-M)、白粉克(dinocap)、滴卓丙(discostrobin)、 腈硫酉昆(dithianon)、嗎菌靈(dodemorph)、多寧(dodine)、益 康。坐(econazole)、乙環嗤(etaconazole)、護粒松 (edifenphos)、氣環唾(epoxiconazole)、乙 σ塞博胺(ethaboxam)、 依瑞莫(ethirimol)、依瑞二嗤(ethridiazole)、°惡唆菌顚I (famoxadone)、口米吐菌酉同(fenamidone)、芬瑞莫(fenarimol)、 115133.doc -48- 200804245 芬克座(fenbuconazole)、芬卡胺(fencaramid)、甲吱醯胺 (fenfuram)、芬酷胺(fenhexamide)、禾草靈(fenoxanil)、拌 種洛(fenpiclonil)、粉鏽淀(fenpropidin)、粉鏽琳 (fenpropimorph)、三苯醋錫、三苯基氫氧化錫、福美鐵 (ferbam)、福作利(ferfurazoate)、σ密菌月宗(ferimzone)、扶吉 胺(fluazinam)、護汰寧(fludioxonil)、氟美醯胺 (flumetover)、氟 σ比菌胺(fluopicolide)、氟氧菌胺 (fluoxastrobin)、氟喹唆(fluquinconazole)、護石夕得 (flusilazole)、石黃菌胺(flusulfamide)、氟多寧(flutolanil)、 護汰芬(flutriafol)、福爾培(folpet)、乙填銘、麥穗靈 (fuberidazole)、吱霜靈(furalaxyl)、福美他(furametapyr)、 己。坐醇(hexaconazole)、惡黴靈(hymexazole)、雙脈鹽 (guazatine)、依滅歹丨J (imazalil)、醯胺嗤(imibenconazole)、 雙脈辛胺(iminoctadine)、依地克(iodicarb)、依普克嗤 (ipconazole)、丙基喜樂松(iprobenfos)、依普同(iprodione)、 綠黴威(iprovalicarb)、異康吐(isoconazole)、稻痕靈 (isoprothiolane)、異替安(isotianil)、春曰黴素(kasugamycin)、 克收欣(kresoxim-methyl)、鏟粉克(mancozeb)、雙快醯菌胺 (mandipropamid)、猛乃浦(maneb)、潘林(mapanipyrin)、 曱雙靈(mefenoxam)、滅鏽胺(mepronil)、滅達樂 (metalaxyl)、葉菌唾(metconazole)、石黃菌威(methasulfocarb)、 免得爛(metiram)、苯氧菌胺(metominostrobin)、滅派林 (mepanipyrim)、美推瑞(metiram)、美曲芬諾(metrafenone)、黴 可峻(miconazole)、邁克尼(myclobutanil)、甲胂鐵銨(neo-asozin) 115133.doc • 49· 200804245 (甲基胂酸鐵)、氟苯哺σ定醇(nuarimol)、辛異嗟吐酮 (octhilinone)、吱醯胺(ofurace)、奥瑞 _ 胺(orysastrobin)、 歐殺斯(oxadixyl)、惡喧酸(oxolinic acid)、惡口米峻 (oxpoconazole)、氧化萎鏽靈(oxycarboxin)、巴克素 (paclobutrazol)、平克座(penconazole)、賓克隆(pencycuron)、 口比 σ塞菌胺(penthiopyrad)、普福作(perfurazoate)、磷酸、苯 酉太(phthalide)、匹苯胺(picobenzamid)、σ定氧菌醋 (picoxystrobin)、多氧菌素(polyoxin)、嗟菌靈(pr〇benazole)、 撲克拉(prochloraz)、撲滅寧(procymidone)、霜黴威 (propamocarb)、霜黴威鹽酸鹽、普克利(propiconazole)、甲 基辞乃浦(propineb)、丙氧啥琳(proquinazid)、丙硫醇克峻 (prothioconazole)、百克敏(pyraclostrobin)、匹作松 (pryazophos)、比芬諾(pyrifenox)、口密黴胺(pyrimethanil)、 口定斑將(pyrifenox)、匹若林(pyrolnitrine)、百快隆 (pyroquilon)、喹唾(quinconazole)、快諾芬(quinoxyfen)、奎 脫辛(quintozene)、石夕硫芬(silthiofam)、石夕氟唾(simeconazole)、 葚孢菌素(spiroxamine)、鏈黴素(streptomycin)、硫、得克 利(tebuconazole)、泰克利(techrazene)、葉枯酞(tecloftalam)、 四氯硝基苯(tecnazene)、氟醚嗅(tetraconazole)、σ塞苯味口坐 (thiabendazole)、赛氟滅(thifluzamide)、多保淨(thiophanate)、 曱基多保淨(thiophanate_methyl)、得恩地(thiram)、汰敵寧 (tiadinil)、脫克松(tolclofos-methyl)、曱基益發靈(tolyfluanid)、 三泰芬(triadimefon)、三泰隆(triadimenol)、。密菌醇 (triarimol)、哺唾唤(triazoxide)、三得芬(tridemorph)、三福 115133.doc -50- 200804245 胺三嗔唆(trimoprhamide tricyclazole)、三敗敏 (trifloxystrobin)、賽福寧(triforine)、環菌唾(triticonazole)、 烯效嗤(uniconazole)、維利微素(validamycin)、免克寧 (vinclozolin)、鋅乃浦(zineb)、益穗(ziram)及氯苯醯胺 (zoxamide);殺線蟲劑,諸如氧洋滅威(aldoxycarb)及苯線 石粦(fenamiphos);殺菌劑,諸如鏈黴素;殺蜗劑,諸如三亞 蜗(amitraz)、滅蜗猛(chinomethionat)、乙醋殺蜗醇 (chlorobenzilate)、環己錫(cyhexatin)、三氯殺瞒醇 (dicofol)、除蜗靈(dienochlor)、乙蜗唾(etoxazole)、奎蜗醚 (fenazaquin)、苯丁錫(fenbutatin oxide)、芬普寧(fenpropathrin)、 芬普蜗(fenpyroximate)、合賽多(hexythiazox)、炔蜗特 (propargite)、比達本(pyridaben)及吡蟎胺(tebufenpyrad); 及生物劑’諸如蘇芸金桿菌、蘇芸 金桿菌δ内黴素、桿狀病毒(baculovirus)及蟲生細菌、病毒 及真菌。此等各種混合搭配物與本發明之化合物之重量比 在100:1與1:100之間,較佳在30:1與1:30之間,更佳在10:1 與1:10之間,且最佳在4:1與1:4之間。 應注意式1之化合物(例如化合物15)與下列物質之組合: 亞托敏、克收欣、三氟敏、百克敏、啶氧菌酯、醚菌胺、 苯氧菌胺/芬氧菌胺(fenominostrobin)、貝芬替、四氣異苯 腈、快諾芬、美曲芬諾、噻芬胺、噁唑菌酮、粉鏽啶、粉 鏽啉、氟氧菌胺、糠菌唑、環克座、苯醚甲環唑、氟環唑、 芬克座、護石夕得、己唾醇、依普克嗤、葉菌嗤、平克座、 普克利、丙氧喹啉、丙硫醇克唑、得克利、環菌唑、撲克 115133.doc -51- 200804245 拉或博克利/尼枯彼芬。 較佳用於更佳控制由真菌植物病原體引起之植物疾病 (例如更低之使用率或更廣泛之所控制植物病原體之範圍) 或抗性管理者為式1之化合物與選自以下群之殺真菌劑的 混合物:亞托敏、氟氧菌胺、克收欣、三氟敏、百克敏、 咬氧菌醋、低莫斯丙(dimoxysixobin)、苯氧菌胺/芬氧菌胺、 快諾芬、美曲芬諾、噻芬胺、粉鏽啶、粉鏽啉、環克座、 粉鏽啉、環克座、氟環唑、護矽得、葉菌唑、普克利、噁 唑菌酮、丙氧喹啉、丙硫醇克唑、得克利及環菌唑。 特定較佳混合物(化合物編號係指索引表A中之化合物) 係選自以下群:化合物7、化合物8、化合物丨5、化合物22 或化合物25與亞托敏之組合,化合物7、化合物8、化合物 15、化合物22或化合物25與氟氧菌胺之組合,化合物7、化 β物8化合物15、化合物22或化合物25與克收欣之組合, 化合物7、化合物8、化合物15、化合物“或化合物25與三 氟敏之組合,化合物7、化合物8、化合物15、化合物。或 化合物25與百克敏之組合,化合物7、化合物8、化合物u、 化合物22或化合物25與絲菌§旨之組合,化合物?、化合物 8、化合物15、化合物22或化合物25與醚菌胺之組合,化合 物7、化合物8、化合物15、化合物如化合物25與苯氧二 胺/芬氧菌胺之組合,化合物7、化合物8、化合物Η、化入 料化合物25與快諾芬之組合,化合物7、化合物8、: 合物15、化合物22或化合物乃與美曲芬諾之組合,化合物 7、化合物8、化合物15、化合物22或化合物。與噻芬:之 115133.doc -52- 200804245 組合,化合物7、化合物8、化合物15、化合物22或化合物 25與粉鏽α疋之組合’化合物7、化合物8、化合物丨5、化合 物22或化合物25與粉鏽啉之組合,化合物7、化合物8、化 合物15、化合物22或化合物25與環克座之組合,化合物7、 化合物8、化合物15、化合物22或化合物乃與氟環唑之組 合,化合物7、化合物8、化合物15、化合物22或化合物% 與護矽得之組合,化合物7、化合物8、化合物15、化合物 22或化合物25與葉菌唑之組合,化合物7、化合物8、化合 物15、化合物22或化合物25與普克利之組合,化合物7、化 合物8、化合物15、化合物22或化合物25與噁唑菌酮之組 合,化合物7、化合物8、化合物15、化合物22或化合物^ 與普克利之組合,化合物7、化合物8、化合物15、化合物 22或化合物25與丙氧喹啉之組合,化合物7、化合物8、化 合物15、化合物22或化合物25與丙硫醇克唑之組合,化合 物7、化合物8、化合物15、化合物22或化合物乃與得克利 之組合,化合物7、化合物8、化合物15、化合 物與環菌嗤之組合。 次匕5 應注意控制大豆植物中由豆薯層鏽菌引起之真菌植物疾 病之方法,其包含應用式1之化合物(例如化合物7、8、15、 22或25)與至少一種選自抑制留醇生物合成中之脫甲基酶 之二唑殺真菌劑的化合物(例如環克座、護矽得及/或得克 利)之組合。亦應注意包含式丨之化合物(例如化合物7、$、 15、22或25)及至少—種選自抑制㈣生物合成中之脫甲基 酶之二唑殺真菌劑的化合物(例如環克座、護矽得及/或得克 115133.doc -53· 200804245 利)之殺真菌組合物。 預防性及、治療性植物疾病控制通常藉由在感染前或感毕 後將有效量之本發明之化合物應用於欲保護之植物之部分 (諸如根、莖、葉、果實、種子、塊莖或球根),或應用於其 中欲保護之植物生長之介質中(土壤或沙地)。亦可將該等化 合物應用於種子以保護種子及幼苗。 此等化合物之施用率可受多種環境因素影響且應在實際 使用條件下測定。當處理葉子時,一般可以小W 5,〇〇〇—g/ha活性成分之比率保護葉子。當處理種子時,一般 可以每么斤種子0.1至10 g之比率保護種子及幼苗。 以下測試證明本發明之化合物對特定病原體之控制功 效。然而,由該等化合物提供之病原體控制保護並不限於 忒等物種。參看索引表a_b之化合物說明。以下縮寫用於下 =索引表中:Me意謂甲基,Et意謂乙基,以意謂丙基 意謂正丙基,kPr意謂異丙基,〇Me意謂甲氧基,〇玢意謂 乙乳基。縮寫"Εχ·”表示”實例”且其後跟隨指示所製備化合 物實例之編號。 口 化合物 2 3
索引表A
(R5a)(R^A (CH3)2CH (CH3)3Si (CHi)3Si R1 R3 R4 Me Cl Cl Et Br cf3 Et Cl cf3 * * 115133.doc -54- 200804245 化合物 (R5a)(R5)2A R1 R3 R4 m.p.fC) 4 (CH3)2CH Et Cl cf3 氺 5 (CH3)3Si Et Br chf2 氺 6 (CH3)3Si Et Cl chf2 氺 7 (Ex. 1) (CH3)2CH Et Br cf3 氺氺 8 (CH3)2CH Et Br chf2 氺 9 (CH3)2CH Et Cl chf2 * 10 (CH3)3Si Me Cl cf3 氺 11 (CH3)3C Et Cl cf3 氺 12 (CH3)3C Et Br cf3 氺 13 ClCH2(CH3)2Si Et Cl cf3 * 14' ClCH2(CH3)2Si Et Br cf3 氺 15 (Ex. 2) (CH3)3Si Et Br OMe 16 (CH3)3Si Et Cl OMe 氺 17 (CH3)3Si /-Pr Cl OMe 氺 18 (CH3)3Si /-Pr Br OMe * 19 ClCH2(CH3)2Si Et Cl chf2 氺 20 ClCH2(CH3)2Si Et Br chf2 * 21 ClCH2(CH3)2Si Et Cl OMe 氺 22 (Ex. 3) (CH3)3Si Et Br ochf2 23 (CH3)3Si Et Cl ochf2 * 24 ClCH2(CH3)2Si Et Br OMe * 25 (CH3)2CH Et Br OMe 氺 26 (ch3)2ch Et Cl OMe 氺 27 (ch3)2ch Et Br ochf2 氺 28 (CH3)2CH Et Cl ochf2 氺 29 (CH3)3Si Me Br cf3 * 30 (CH3)2CH i-Pr Br OMe 氺 31 (CH3)2CH n-Pr Br OMe 氺 32 (ch3)2ch /-Pr Cl OMe 33 (ch3)2ch n-Pr Cl OMe * 34 (CH3)3Si /-Pr Br cf3 * .35 (CH3)3Si z-Pr Cl cf3 ie 36 (CH3)2CH Et Br OEt 37 (ch3)2ch Et Cl OEt 38 (ch3)2ch n-Vx Br OEt 39 (ch3)2ch n-Pi Cl OEt it 40 (ch3)2ch /-Pr Br OEt 氺 41 (ch3)2ch /-Pr Cl OEt ie 42 (CH3)3Si Et Br OEt 氺 43 (CH3)3Si Et Cl OEt 氺 44 (CH3)3Si n-Pr Cl OEt * b NMR資料參看索引表B。** iHNMR資料參看合成實例。 115133.doc -55- 200804245
索引表B 化合物 編號 iHNMR資料(CDC13溶液,除非另外指出)a 1 δ 7.4 (s,1H),6.9 (s,1H),3.9 (t,2H),3.0 (s,6H),1.8 (m,2H),1.6 (m,1H),1.3 (t5 2H),0.95 (d,6H)。 2 δ 7.3-7.5 (br,1H),7·18 (s,1H),7·03 (s,1H),3·94 (t,2H),3.24-3.6 (br,2H),3·03 (s,3H),1.79 (m,2H),1·24 (t,3H),0.58 (m,2H),0.02 (s,9H)。 3 δ 7.3-7.5 (br,1H),7.08 (s,1H),7 (s,1H),3.93 (t,2H),3·24-3·6 (br,2H),3·03 (s, 3H),1.79 (m,2H),1.23 (t,3H),0.58 (m,2H),0.02 (s,9H)。 4 δ 7.3-7.5 (br5 1H),7.06 (s,1H),7 (s,1H),3.96 (t,2H),3.24-3.6 (br,2H),3·03 (s, 3H),1.8 (m,2H),1.6 (m,1H),1.35 (m,2H),1.23 (t,3H),0.91 (d,6H)。 5 δ 7.3-7.5 (br5 1H),7·12 (s,1H),7_04 (s5 1H),6.9 (t,1H),3·91 (t5 2H),3.24-3.6 (br,2H),3.03 (s,3H),1.79 (m,2H),1.23 (t,3H),0.58 (m,2H),0.02 (s,9H)。 6 δ 7.3-7.6 (br,1H),6.7-7.1 (m,3H),3.91 (t,2H),3.24-3.6 (br5 2H),3.03 (s,3H), 1.79 (m,2H),1.23 (t,3H),0.61 (m,2H),0.02 (s,9H)。 8 δ 7.3-7.5 (br,1H),7·13 (s,1H),6.7-7.07 (m,2H),3·94 (t,2H),3.24-3.6 (br,2H), 3.03 (s,3H),1.78 (m5 2H),1·6 (m,1H),1.35 (m,2H),1.23 (t,3H),0.91 (d,6H)。 9 δ 7.3-7.6 (br5 1H),6.7-7.08 (m,3H),3.94 (t5 2H),3.24-3.6 (br,2H),3·03 (s5 3H), 1.8 (m5 2H),1·6 (m,1H),1.35 (m,2H),1.23 (t,3H),0.92 (d,6H)。 10 δ 7·44 (s,1H),7.07 (s5 1H),6·99 (s51H),3.93 (t,2H),3·05 (s,6H),1.79 (m,2H), 0.59 (m,2H),0.02 (s,9H)。 11 δ 7.3-7.5 (br,1H),7.08 (s5 1H),7 (s,1H),3.95 (t,2H),3·24-3·6 (br,2H),3·03 (s5 3H),1.79 (m,2H),1.2-1.4 (m,5H),0·91 (s,9H)。 12 δ 7.3-7.5 (br,1H),7.18 (s,1H),7.04 (s,1H),3.95 (t,2H),3.24-3.6 (br,2H),3.03 (s,3H),1.78 (m,2H),1.33 (m,2H),1.24 (t,3H),0.91 (s,9H)。 13 δ 7.3-7.5 (br,1H),7.08 (s,1H),6·99 (s,1H),3.95 (t,2H),3.24-3.6 (br,2H),3.03 (s,3H),2.81 (s,2H),1.82 (m,2H),1.23 (t,3H),0·78 (m,2H),0.14 (s,6H)。 14 δ 7.3-7.5 (br,1H),7.18 (s,1H),7.04 (s,1H),3·95 (t5 2H),3·24-3·6 (br,2H),3.03 (s, 3H),2.81 (s,2HX 1.82 (m,2H),1.24 (t,3H),0.78 (m,2H),0.14 (s,6H)。 16 δ 7.3-7.7 (br,lH),6.87 (s,1H),6.46 (s,1H),3.9 (t,2H),3.84 (s,3H),3.2-3.6 (br, 2H),3.02 (s,3H),1.82 (m,2H),1.23 (t,3H),0.6 (m,2H)5 0.01 (s,9H)。 17 δ 7.5-7.6 (br,1H),6.87 (s,1H),6.48 (s,1H),3.9 (t5 2H),3·84 (s,3H),3·55-3·8 (br,1H),2·94 (s,3H),1.82 (m,2H),1.26 (d,6H),0.56 (m,2H),0.01 (s,9H)。 18 δ 7·55 φτ,1Η),7.03 (s5 1H),6.48 (s,1H),3·9 (t,2H),3.84 (s,3H),3.55-3.8 (br, 1H),2.94 (s,3H),1.82 (m,2H),1.25 (d,6H),0.56 (m,2H),0.01 (s,9H)。 19 δ 7.3-7.6 (br5 1H),6.7-7.1 (m,3H),3.93 (t,2H),3.24-3.6 (br,2H),3.03 (s,3H), 2.81 (s,2H),1.82 (m,2H),1.23 (t,3H),0.78 (m,2H),0.15 (s,6H)。 20 δ 7.3-7.6 (br,1H),6.7-7.12 (m,3H),3.93 (t5 2H),3.24-3.6 (br,2H),3·03 (s,3H), 2.81 (s,2H),1.82 (m,2H),1.24 (t,3H),0.78 (m,2H),0.15 (s,6H)。 115133.doc -56 - 200804245 化合物 編號 ^NMR資料(CDC13溶液,除非另外指出)a 21 δ 7.3-7.6 (br,1H),6.87 (s,1H),6.46 (s,1H),3.91 (t,2H),3.84 (s5 3H),3.2-3.6 (br,2H),3·03 (s,3H),2.81 (s,2H),1.87 (m,2H),1.23 (t5 3H),0.78 (m,2H),0·15 (s5 6H)〇 23 δ 7.27-7.5 (br,1H),6·97 (s,1H),6.72 (s,1H),6.54 (t,1H),3.91 (t5 2H),3·2-3·6 (br5 2H),3·02 (s,3H),1.79 (m,2H),1.23 (t,3H),0.6 (m,2H),0.02 (s,9H)。 24 δ 7.3-7.5 (br,1H),7.03 (s,1H),6.48 (s,1H),3.91 (t,2H),3.83 (s,3H),3.24-3.6 (br,2H)5 3.02 (s,3H),2.81 (s,2H),1.84 (m,2H),1.24 (t5 3H),0.78 (m,2H),0·14 (s,6H)。 25 δ 7.3-7.5 (br,1H),7.03 (s,1H),6.48 (s,1H),3.93 (t,2H),3.83 (s,3H),3.24-3.6 (br,2H),3.02 (s5 3H),1.82 (m,2H), 1.6 (m,1H),1.34 (m,2H),1.23 (t5 3H),0.91 (d, 6H) 〇 26 δ 7.3-7.56 (br,1H),6.87 (s,1H),6.46 (s51H),3.93 (t5 2H),3.83 (s,3H),3·24-3·6 (br,2H),3.02 (s,3H),1.82 (m,2H)5 1·6 (m,1H),1.34 (m,2H),1.23 (t5 3H),0.91 (d,6H) 〇 27 δ 7.3-7.5 (br5 1H),7.15 (s,1H), 6·72 (s,1H),6.53 (t5 1H),3·93 (t,2H),3.24-3.6 (br,2H),3.02 (s,3H),1.8 (m,2H),1.6 (m,1H),1.34 (m,2H),1.23 (t5 3H),0.92 (d5 6H) 〇 28 δ 7.3-7.56 (br,1H),6.25-7 (m,3H),3.93 (t,2H),3.24-3.6 (br,2H),3.02 (s,3H), 1.8 (m,2H),1.62 (m,1H),1.35 (m,2H),1.22 (t,3H),0.92 (d,6H)。 29 δ 7.42 (s,1H),7.18 (s,1H),7.05 (s,1H),3.94 (t,2H),3.05 (s5 6H),1.79 (m,2H), 0.63 (m,2H),0.02 (s,9H)。 30 δ 7.3-7.6 (br,1H),7.03 (s,1H),6.48 (s,1H),3.92 (t5 2H),3.83 (s,3H)5 3.55-3.8 (br,1H),2.94 (s,3H),1.82 (m,2H),1·6 (m,1H),1.34 (m,2H),1.26 (d,6H),0.91 (d5 6H) 〇 31 δ 7.35-7.5 (br,1H),7.03 (s,1H),6.46 (s,1H),3.92 (t,2H),3.83 (s,3H),3.1-3.5 (br,2H),3.02 (s,3H),1.82 (m,2H),1.62 (m,3H),L32 (m,2H),0_92 (m,9H)。 32 δ 7.3-7.6 (br,1H),6.87 (s,1H),6.47 (s,1H),3.93 (t,2H),3.83 (s,3H),3.58-3.78 (br,1H),2.94 (s,3H),1.82 (m,2H),1.6 (m,1H),1.34 (m5 2H),1.25 (d,6H),0.91 (d5 6H)。 33 δ 7.3-7.5 (br,1H),6.87 (s,1H),6.46 (s5 1H),3·93 (t5 2H),3.83 (s,3H),3.1-3.5 (br,2H),3.02 (s5 3H),1.82 (m,2H),1.62 (m5 3H),1·32 (m5 2H),0·92 (m,9H)。 34 δ 7.3-7.6 (br,1H),7·18 (s,1H),7.04 (s,1H),3.93 (t,2HX 3.6-3.8 (br,1H),2.95 (s5 3H),1.8 (m,2H),1.25 (d,6H),0.59 (m,2H),0.02 (s,9H)。 35 δ 7.3-7.6 (br5 1H),7.08 (s,1H), 6.99 (s,1H),3.93 (t5 2H),3.6-3.8 (br,1H),2.95 (s,3H),1.8 (m,2H),1.25 (d5 6H),0.6 (m,2H),0.02 (s,9H)。 36 δ 7.3-7.5 (br,1H),7.04 (s,1H),6.5 (s5 1H),4.05 (q,2H),3.92 (t,2H),3.24-3.6 (br,2H),3.02 (s,3H),1.8 (m,2H),1.6 (m,1H),1.42 (t,3H),1.34 (m,2H),1.23 (t,3H),0.91 (d,6H)。 115133.doc -57- 200804245 化合物 編號 hNMR資料(CDC13溶液,除非另外指出)a 37 δ 7.3-7.5 (br,1H),6.88 (s,1H),6.48 (s,1H),4·05 (q,2H),3·92 (t,2H),3.24-3.6 (br,2Η), 3·02 (s,3Η),1·8 (m,2Η),1·6 (m5 1Η),1·42 (t,3Η),1·35 (m,2Η),1·23 (t,3Η),0.91 (d,6Η)。 38 δ 7.3-7.5 (br,1H),7·05 (s,1H),6.48 (s,1H),4.05 (q,2H),3.92 (t,2H),3.1-3.5 (br,2H),3.02 (s, 3H),1.8 (m,2H),1.62 (m,3H),1.42 (t,3H),1.34 (m,2H),0.91 (m,9H) 〇 39 δ 7.35-7.5 (br5 1H),6.88 (s,1H),6.48 (s51H),4·05 (q,2H),3.92 (t,2HX 3.1-3.5 (br,2H),3.02 (s,3H),1.8 (m,2H),1.62 (m5 3H),1·41 (t,3H),1.34 (m,2H),0.91 (m,9H) 〇 40 δ 7.3-7.6 (br,1H),7.05 (s,1H),6.48 (s,1H),4.05 (q,2H),3.92 (t5 2H),3.55-3.7 (br,1H),2.94 (s,3H),1.8 (m,2H),1.62 (m,1H),1.42 (t,3H),1.34 (m,2H),1.25 (d,6H),0.91 (d,6H)。 41 δ 7.3-7.6 (br,1H),6.88 (s5 1H),6.48 (s,1H),4.05 (q5 2H),3.92 (t,2H),3.55-3.7 (br,1H),2.94 (s,3H),1.8 (m,2H),1.62 (m,1H),1.42 (t,3H),1.34 (m,2H),1.25 (d,6H),0.91 (d,6H)。 42 δ 7.27-7.56 (br,1H),7·04 (s,1H),6.46 (s,1H),4.05 (q,2H),3.89 (t,2H),3.2-3.6 (br,2H),3.02 (s,3H),1.8 (m5 2H), 1.42 (t5 3H),1·23 (t,3H),0.58 (m,2H),0.02 (s,9H)。 43 δ 7.27-7.56 (hr5 1H)? 6.88 (s, 1H)? 6.48 (s, 1H)? 4.05 (q3 2H)5 3.9 (t5 2H), 3.2-3.6 (br,2H),3.02 (s,3H),1.8 (m,2H),1.42 (t5 3H),1.22 (t,3H),0.58 (m,2H),0.01 (s,9H)〇 44 δ 7.3-7.56 (br,1H),6.87 (s,1H),6.46 (s,1H),4.04 (q,2H),3.89 (t,2H),3.1-3.5 (br,2H),3·01 (s5 3H),1.8 (m,2H),1.62 (m,2H),1.41 (t,3H),0.92 (m,3H),0.58 (m,2H),0.01 (s,9H)。 4 NMR資料係以ppm四甲基矽烷低磁場計。耦合由(s)-單 峰、(d)-雙峰、⑴_三峰、(q)-四峰、(m)_多峰、(br)-寬峰 表示。 本發明之生物實例 製備測試懸浮液之一般方案··首先將測試化合物以等於 3%最終體積之量溶於丙酮中且隨後以所需濃度(以ρριη計) 懸浮於含有250 ppm之界面活性劑Trxm® 〇14(多元醇酯)之 丙酮及純水(以50/50混合)中。隨後將所得測試懸浮液用於 以下測試中。 115133.doc •58- 200804245
測試A 將測試懸浮液以4〇 ppm(相當於120 g/ha之比率)噴灑於小 麥幼苗上至溢流點。第二天,將幼苗以小麥鏽菌之孢子懸 浮液(小麥褐鏽病之引發劑)接種且在20t:下於飽和氣氛中 培育24小時,且隨後移至生長箱中,在2〇〇c下歷時6天,其 後進行疾病評定。
測試B 將測試懸浮液以40 Ppm(相當於120 g/ha之比率)噴灌於小 ’ 麥幼苗上至溢流點。第二天,將幼苗以小麥白粉病菌之孢 子粉塵(小麥白粉病之引發劑)接種,且在2〇r下在生長箱中 培育7天,其後進行疾病評定。
測試C 將測試懸浮液以20 g/ha(以1000 L/ha之應用體積)喷灑於 葡萄幼苗上。第二天,將幼苗以葡萄白粉病菌之孢子懸浮 液(葡萄白粉病之引發劑)接種,且在溫室中在20°C下培育14 天’其後進行疾病評定。
測試D 將測試懸浮液以1〇〇 g/ha(以1〇〇〇 L/ha之應用體積)噴灑 於大豆幼苗上。第二天,在20°C下於飽和氣氛下將幼苗培 育48h ’且隨後移至生長箱中,在22°C下歷時14天,其後進 行作物安全性評定。
測試E 將測試懸浮液以2〇 g/ha(以1〇〇〇 L/ha之應用體積)噴灑於 大丑幼苗上。第二天,在20°C下於飽和氣氛下將幼苗培育 115133.doc -59- 200804245 48小時’且隨後移至生長箱中,在饥下歷時^,其後 進行作物安全性評定。 測試A-E之結果給於表a中。對測試A_c而言,疾病功效 評定係以無可見症狀之葉面積之百分比計,以總葉㈣之 百分比表示(〇至100%),例如評定值1〇〇指示1〇〇%疾病控制 且評定值0指示無疾病控制(相對於對照而言卜短劃線㈠指 不無測試結果。對測試D-E而言’作物安全性評定以展示損 傷之葉面積之百分比計,以總葉面積之百分比表示至 100%) ’例如評定值1〇〇指示1〇〇%作物損傷且評定值〇指示 無作物損傷。在百分比評定值後之字母符號指示所觀察到 之症狀類型,,’B”指示壞死且"η"指示激素效應。短劃線㈠ 指示無測試結果。測試A_E之結果指示化合物在控制穀類及 闊葉作物之鏽病及白粉病上為有效的,且有利於在闊葉作 物上使用。表A之化合物編號係指索引表a中之化合物。
表A 化合物編號 測試A 測試B 測試C 測試D 測試E 1 0 21 一 2 100 100 100 3 100 100 100 10H 0 4 100 100 82 0 0 5 100 100 - 6 100 100 - 7 100 100 87 0 0 8 100 100 98 0 0 9 100 99 89 12 B 0 10 100 100 67 11 100 100 一 12 100 100 100 13 100 100 100 - - 115133.doc -60- 200804245 化合物編號 測試A 測試B 測試C 測試D 測試E 14 100 100 - - 15 99 97 99 3B 0 16 99 97 97 10B 0 17 100 99 93 10B 0 18 100 100 100 0 0 19 100 100 99 - - 20 100 100 - - - 21 100 99 100 9H 0 22 100 100 95 0 0 23 100 100 100 13 B 0 24 100 98 100 7B 0 25 100 99 97 0 0 26 100 99 100 7B 0 27 99 99 - 麵 - 28 100 99 - - - 29 99 100 - - — 30 99 60 97 0 0 31 91 0 100 0 0 32 99 93 - - - 33 91 32 - 两 34 99 100 - - - 35 - - - - 36 100 72 - - - 37 100 93 讎 - 麵 38 55 0 - - - 39 0 0 - - - 40 99 62 - - - 41 99 86 - - 42 100 98 - - - 43 100 99 - - - 44 0 54 - - - 在重複之大豆田間試驗中,評估三種化合物對於由病原 體豆薯層鏽菌引起之亞洲大豆鏽病之控制。將各化合物調 配成可乳化之濃縮物,分散於水中且隨後用大田喷霧機以 115133.doc -61 - 200804245 200公升/Ha應用。各化合物以三個額定值(50、100及200公 克活性/Ha)且在兩個應用時期應用,即在R1階段(第一次可 見花芽)及R 5階段(開花結束)。包括兩種商業標準以用於比 較。隨後對治療進行評估其在低遮蓬中四個重複中之每一 者之疾病百分比(可見症狀之葉面積之百分比)且表示為相 對於未治療對照之控制百分比。對於該等化合物中之任一 者,未觀察到植物損傷。 結果在表B中給出。疾病功效評定值係表示為總葉面積之 百分比(0至100%),例如評定值100指示100%疾病控制且評 定值0指示無疾病控制(相對於對照而言)。"DAT1"係指在第 一次喷霧應用後之天數(T1)。表B之化合物編號係指索引表 A中之化合物。
表B 化合物編號 比率(gai/Ha) 14DAT1 控制 % 21 0八11控制% 28DAT1 控制 % 7 50 36 59 47 7 100 21 55 50 7 200 53 84 61 15 50 34 62 55 15 100 43 51 58 15 200 43 64 64 22 50 1 32 21 22 100 29 46 31 22 200 24 65 51 115133.doc •62-
Claims (1)
- 200804245 十、申請專利範圍: 1· 一種選自式1化合物、其N-氧化物及其農業上適合之鹽之 化合物,其中 R1為cvc4烷基或c3-c4環烷基; R為烧基; R3 為 Br、C1或 I ; R4為ci ;或心—匕烷基或Cl-C2烷氧基,該Cl-c2烷基或 Ci-C2烷氧基各視情況經一至三個獨立地選自鹵素 之取代基取代; A為C或Si ; r5各自獨立地為視情況經一至三個獨立地選自鹵素之 取代基取代之CKC2烷基;且 烷基; 其限制條件為當A為Si時,則11^為〇:1-(:2烷基。 2.如請求項丨之化合物,其中 Rl為CVC3烷基或c3-C4環烷基; R2為(VC2烷基; R3 為 Br 或 C1 ; R4為C1 ;或(^-0:2烷基或CVC2烷氧基,該CVC2烷基或 115133.doc 200804245 Cl C2烷氧I各視情況經-至三個獨立地選自F及 C1之取代基取代;且 R各自獨立地為視情況妳一 5 - ΓΛ Jb况經一至二個獨立地選自F及C1 之取代基取代之CrC2烷基。 3 ·如請求項2之化合物,其中, 1^為(^(:2烷基; R2為曱基; R3 為 Br ; R4為ci ;或匕弋2烷基或Cl_C2烷氧基,該Ci_C2烷基或 C 1 C 2烧乳基各視情況經一至三個F取代;且 R各自獨立地為視情況經一至三個c 1取代之ci_c2烧 基。 4·如請求項3之化合物,其中 R1為乙基; R2為曱基; 汉4為<^烷基或Cl烷氧基,該等基團各視情況經一至三 個F取代;且 r5各自獨立地為視情況經一至三個C1取代之q烧基。 5 · 一種如請求項1之化合物,其係選自由下列各物組成之 群: #’-|>溴_4-[(4-甲基戊基)氧基]-5-(三氟甲基)苯基>ΛΓ_ 乙基省-甲基甲醯亞胺醯胺, #'•[2-溴_5_甲氧基-4_[3_(三甲基矽烷基)丙氧基]苯 基乙基]^-甲基甲醯亞胺醯胺, 115133.doc 200804245 #-[2-溴-5-(二氟甲氧基)_4_[3_(三甲基矽烷基)丙氧基] 本基]乙基-7V-甲基甲酿亞胺醯胺, #’-[2-溴-5-(二說曱基)-4_[(4_甲基戊基)氧基]苯基] 乙基甲基甲醯亞胺醯胺;及 #’-[2-溴-5-甲氧基_4_[(4_甲基戊基)氧基]苯基]_…乙基 甲基甲醯亞胺醯胺。 6· -種殺真菌組合物,其包含殺真菌有效量之如請求項κ 化〇物及至少一種選自由界面活性劑、固體稀釋劑或液 體稀釋劑組成之群之額外組份,該組合物視情況進一步 包含有效量之至少一種額外生物活性化合物或藥劑。 7· —種殺真菌組合物,其包含⑷如請求項i之化合物;及⑻ 至少一種其他殺真菌劑。 8.如明求項7之机真菌組合物,其包含其中該(b)組份包括至 少種選自二唑殺真菌劑的化合物,該化合物可抑制甾 醇生物合成作用之脫曱基酶。 9· 一種控制穀類或闊葉作物中至少一種植物真菌疾病之方 法,該真菌疾病係選自由下列疾病組成之群:由白粉菌 (心州spp)、葡萄白粉菌·⑽/a 、甜瓜白 粉菌(办/m㈣咖ca /w/如㈣及蘋果白粉菌(〜而咖“㈣ /ewcoWc/m)引起之白粉病;由長螺孢菌 (Helminthosporium sVV)、大麥網斑病蛰(Pyren〇ph〇ra 及大麥雲紋病函(及引起之疾 病;及由柄鏽菌spp)、咖啡駝孢鏽菌(沒㈣心。 vastatrix)、I I 鐵病儀(jjromyCes appenc^icuiatus、、欠瓦 115133.doc 200804245 鏽 MPhakopsora pachyrhizi、反亙薯墙鎢蛰㈣—ρ_ 如)引起之鏽病,該方法包含: =殺真菌有效量之如請求項!之化合物施用於該植物 或其部分或施用於該植物種子或幼苗。 ίο. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21 如請求項9之方法,其中至少一種白粉病受到控制。 如請求項U)之方法’其中該真菌疾病係由小麥白粉病菌 ⑽e以⑽〜以f· sp 引起。 如請求項Η)之方法’其中該真菌疾病係由大麥白粉病菌 (Erysiphe graminis L 叩 h〇rde⑺'起。 如請求項H)之方法’其中該真菌疾病係由葡萄白粉病菌 引起。 如請求項Η)之方法,其中該真菌疾病係由蘋果白粉病菌 引起。 如請求項9之方法,其中至少一種鏽病受到控制。 如請求項15之方法,其中該真菌疾病係由小麥鏽菌 (Puccinia recondita)引起。 如明求項1 5之方法,其中該真菌疾病係由條形柄鏽菌 (Puccinia striif〇rmis、M 爽。 如請求項15之方法,其中該真菌疾病係由禾柄鏽菌 gram/mi)引起。 如明求項15之方法,其中該真菌疾病係由咖徘騎孢鏽菌 (Femz7ez’a vawairix)引起。 如請求項15之方法,其中該真菌疾病係由菜豆鏽病菌 (Uromyces appendiculatus)弓\ 起。 如凊求項15之方法,其中該真菌疾病係由豆薯層鏽菌引 115133.doc 200804245 起。 22·如請求項21之方法,其中在大豆植物 把夕亩1¾从姑从严. 中由丑箸層鏽菌引 I之真卤性植物疾病受到控制; ^ 亥方法包含施用化合 物之組合,該化合物包括至少一 人忐你田由夕m?田I A 喱k自可抑制留醇生物 口成作用中之脫曱基酶之三唑殺真菌劑的化合物。 23.如請求項9至21中任一項之方 ,、甲遠植物為雙子葉作 物024·如請求項23之方法萄及葫蘆。 其中该雙子葉作物係選自大豆、葡 25. 如請求項24之方法,其中該雙子葉作物為大豆。 26. 如請求項24之方法,其中該雙子葉作物為葡萄。 27. 如請求項24之方法,其中該雙子葉作物為葫蘆。 28. —種控制由子囊菌植物病原體引起之植物疾病之方法 其包含: 將殺真菌有效量之如請求項丨之化合物施用於該植物 或其部分或施用於該植物種子或幼苗上。 29· —種控制由擔子菌植物病原體引起之植物疾病之方法, 其包含: 將殺真菌有效量之如請求項丨之化合物施用於該植物 或其部分或施應用於該植物種子或幼苗上。 3 0· —種控制除由除子囊菌植物病原體及擔子菌植物病原體 以外之植物病原體引起之植物疾病的方法,其包含: 將殺真菌有效量之如請求項1之化合物施用於該植物 或其部分或施用於該植物種子或幼苗上。 31·如請求項28、29或30之方法,其中該植物為雙子葉作物。 115133.doc 200804245 七、指定代表圖: (一) 本案指定代表圖為:(無) (二) 本代表圖之元件符號簡單說明: 八、本案若有化學式時,請揭示最能顯示發明特徵的化學式:115133.doc
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BR112013010850A8 (pt) | 2010-11-05 | 2018-06-12 | Otsuka Agritechno Co Ltd | Composto de etinilfenilamidina ou sal do mesmo, método para produzir o mesmo e fungicida para uso agrícola e em horticultura |
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BR112018000390A2 (pt) | 2015-07-08 | 2018-09-11 | Bayer Cropscience Ag | fenoxihalogenofenilamidinas e o uso dessas como fungicidas |
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TW201838965A (zh) | 2017-04-20 | 2018-11-01 | 印度商Pi工業公司 | 新穎的苯胺化合物 |
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