CN1336918A - 作为除草剂的取代的2-苯基吡啶 - Google Patents
作为除草剂的取代的2-苯基吡啶 Download PDFInfo
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- CN1336918A CN1336918A CN00802838A CN00802838A CN1336918A CN 1336918 A CN1336918 A CN 1336918A CN 00802838 A CN00802838 A CN 00802838A CN 00802838 A CN00802838 A CN 00802838A CN 1336918 A CN1336918 A CN 1336918A
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- Prior art keywords
- och
- alkyl
- formula
- alkoxy
- hydrogen
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- 150000005360 2-phenylpyridines Chemical class 0.000 title claims abstract description 31
- 239000004009 herbicide Substances 0.000 title claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 230000035613 defoliation Effects 0.000 claims abstract description 13
- -1 cyano, hydroxy Chemical group 0.000 claims description 292
- 150000001875 compounds Chemical class 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 54
- 239000000460 chlorine Substances 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 230000002363 herbicidal effect Effects 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 229920000742 Cotton Polymers 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 5
- 239000002274 desiccant Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 150000005749 2-halopyridines Chemical class 0.000 claims description 4
- 229910003106 Zn-Br Inorganic materials 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000002837 defoliant Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims 8
- 239000007788 liquid Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000003701 inert diluent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 430
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 243
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 76
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 26
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 7
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 241000219146 Gossypium Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012954 diazonium Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 4
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 4
- 125000006519 CCH3 Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229940125890 compound Ia Drugs 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 3
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 3
- 240000002024 Gossypium herbaceum Species 0.000 description 3
- 235000003222 Helianthus annuus Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Chemical group 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 230000007480 spreading Effects 0.000 description 3
- 125000005537 sulfoxonium group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZWUBSOYJEJHMRR-UHFFFAOYSA-N (5,6-dichloropyridin-3-yl) acetate Chemical compound CC(=O)OC1=CN=C(Cl)C(Cl)=C1 ZWUBSOYJEJHMRR-UHFFFAOYSA-N 0.000 description 2
- HDIONPLBWPXAMY-UHFFFAOYSA-N (5,6-dichloropyridin-3-yl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CN=C(Cl)C(Cl)=C1 HDIONPLBWPXAMY-UHFFFAOYSA-N 0.000 description 2
- XLPDVAVQKGDHNO-UHFFFAOYSA-N 2,3-dichloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CN=C(Cl)C(Cl)=C1 XLPDVAVQKGDHNO-UHFFFAOYSA-N 0.000 description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- GTOXJMNILNYXLE-UHFFFAOYSA-N 3-chloro-5-nitro-1h-pyridin-2-one Chemical compound OC1=NC=C([N+]([O-])=O)C=C1Cl GTOXJMNILNYXLE-UHFFFAOYSA-N 0.000 description 2
- XTCHZNJJTQACES-UHFFFAOYSA-N 5,6-dichloropyridin-3-amine Chemical compound NC1=CN=C(Cl)C(Cl)=C1 XTCHZNJJTQACES-UHFFFAOYSA-N 0.000 description 2
- GMHPKIGFTDRQBP-UHFFFAOYSA-N 5,6-dichloropyridin-3-ol Chemical compound OC1=CN=C(Cl)C(Cl)=C1 GMHPKIGFTDRQBP-UHFFFAOYSA-N 0.000 description 2
- FLIQYTXJLWGVBG-UHFFFAOYSA-N 6-phenylpyridin-3-amine Chemical compound N1=CC(N)=CC=C1C1=CC=CC=C1 FLIQYTXJLWGVBG-UHFFFAOYSA-N 0.000 description 2
- UAUCJEGMDDNGCV-UHFFFAOYSA-N 6-phenylpyridin-3-ol Chemical compound N1=CC(O)=CC=C1C1=CC=CC=C1 UAUCJEGMDDNGCV-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
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- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 2
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 2
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- 125000002412 n-penten-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002504 n-penten-4-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- JLPJFSCQKHRSQR-UHFFFAOYSA-N oxolan-3-one Chemical compound O=C1CCOC1 JLPJFSCQKHRSQR-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 235000018322 upland cotton Nutrition 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明涉及取代的2-苯基吡啶(I)及其盐,涉及作为除草剂用于植物干燥/落叶的用途。
Description
本发明涉及式I的新颖取代的2-苯基吡啶,其中:n是0或1;R1是氨基磺酰基,C1-C6-烷基亚磺酰基,C1-C6-烷基磺酰基或C1-C6-卤代烷基磺酰基;R2,R3彼此独立地是氢或卤素;R4是氰基,羟基,卤素,C1-C6-烷氧基或苯基甲氧基,其中该苯基环可以是未取代的或可以携带自1至3个取代基,在每种情况取代基选自羟基,卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-卤代烷氧基,羟基羰基,(C1-C6-烷氧基)羰基和(C1-C6-烷氧基)羰基-C1-C6-烷氧基;R5是氢,硝基,氰基,羟基氨基,卤素,C1-C6-烷基,C1-C6-卤代烷基,-COCl,-CO-OR6,-CO-N(R7)R8,-CO-O-(C1-C4-亚烷基)-CO-OR6,-CO-O-(C1-C4-亚烷基)-CO-N(R7)R8,-X1-(C1-C4-亚烷基)-CO-R6,-X1-(C1-C4-亚烷基)-CO-OR6,-X1-(C1-C4-亚烷基)-CO-O-(C1-C4-亚烷基)-CO-OR6,-X1-(C1-C4-亚烷基)-CO-N(R7)R8,-X1-R9,-CH=C(R10)-CO-OR6,-CH=C(R10)-CO-O-(C1-C4-亚烷基)-CO-OR6,-CH=C(R10)-CO-N(R7)R8,甲酰基,-CO-R6,-C(R8)=N-OR15,-X1-(C1-C4-亚烷基)-C(R8)=N-OR15,-CH=C(R10)-C(R8)=N-OR15,-CH(C1-C6-烷氧基)2,-N(R16)R17,-N(R16)-SO2-(C1-C6-烷基),-N(R16)-CO-(C1-C6-烷基),氯磺酰基,羟基磺酰基或-SO2-N(R18)R19;R6是氢,C1-C6-烷基,C1-C6-卤代烷基,C3-C6-链烯基,C3-C6-炔基,C3-C6-环烷基或C1-C6-烷氧基-C1-C6-烷基;R7是氢或C1-C6-烷基;R8是氢,羟基,C1-C6-烷基,羟基羰基-C1-C6-烷基,(C1-C6-烷氧基)羰基-C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷氧基,苯基-C1-C6-烷氧基,C3-C6-链烯氧基或C3-C6-炔氧基;R9是氢,C1-C6-烷基,C1-C6-卤代烷基,C3-C6-链烯基,C3-C6-炔基,C3-C6-环烷基或C1-C6-烷氧基-C1-C6-烷基;R10是氢,卤素或C1-C6-烷基;R11-R14彼此独立地是氢,C1-C6-烷基或(C1-C6-烷氧基)羰基;R15是氢,C1-C6-烷基,苯基-C1-C6-烷基,(C1-C6-烷氧基)羰基-C1-C6-烷基,C3-C6链烯基或C3-C6-炔基;R16是氢或C1-C6-烷基;R17是氢,C1-C6-烷基,羟基羰基-C1-C6-烷基,(C1-C6-烷氧基)羰基-C1-C6-烷基或C1-C6-烷氧基;R18是氢或C1-C6-烷基;R19是氢,C1-C6-烷基,羟基羰基-C1-C6-烷基,(C1-C6-烷氧基)羰基-C1-C6-烷基或C1-C6-烷氧基;X1-X3彼此独立地是氧或硫;以及其中R6=氢的化合物I的农业上可用的盐。
此外,本发明涉及
-化合物I作为除草剂或用于植物的干燥/落叶的用途,
-包含化合物I作为活性成分的除草组合物和用于植物的干燥和/或落叶的组合物,
-使用化合物I控制不受欢迎的植物及使植物干燥和/或落叶的方法,
-用于制备化合物I以及使用化合物I的除草组合物和植物干燥和/或
落叶用组合物的方法,还有
-式IIa的中间体。
WO96/21646和WO96/21647已描述了化合物I类型的某些取代的2-苯基吡啶,尤其在该吡啶环的5-位置具有C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基,用作除草剂及干燥剂/落叶剂。
此外,具有除草和/或干燥/落叶活性的2-苯基吡啶,其与本发明化合物I的不同在于R1直接连接至该吡啶环,形成WO98/07700的主题的一部分。
然而,现有技术化合物的除草活性,就对有害植物而言,不是经常完全令人满意。
因此,本发明的一个目的是提供新颖除草活性化合物,其比已知的化合物对不受欢迎的植物有更佳的选择性控制。另一个目的是提供具有干燥/落叶作用的新颖化合物。
我们已发现由在开始时定义的式I的具有除草作用的取代2-苯基吡啶及其制备所用新颖中间体IIa实现这些目的。
此外,我们已发现包含化合物I且具有非常良好的除草活性的除草组合物。此外,我们已发现用于制备这些组合物的方法及使用该化合物I控制不受欢迎的植物的方法。
此外,我们已发现该化合物I也适合用于植物的部分的干燥/落叶。适当的植物是禾谷类作物诸如棉花,马铃薯,油菜,葵花,大豆或蚕豆,特别是棉花及马铃薯。关于此点,我们已发现用于植物干燥和/或落叶的组合物,用于制备这些组合物的方法及使用该化合物I使植物干燥和/或落叶的方法。
取决于取代的模式,该式I的化合物可以含一个或多个手性中心,在该情况它们以对映体或非对映异构体混合物形式存在。本发明提供纯对映体或非对映异构体两者及其混合物。
其中R6=氢的取代的2-苯基吡啶I可以以其农业上可用的盐形式存在,盐的类型通常并不重要。一般而言,当其除草活性与该游离化合物I比较没有受不利影响时,此类碱的盐是适当的。
适当的盐特别是碱金属盐,优选钠和钾盐,碱土金属盐,优选钙和镁盐,过渡金属盐,优选锌和铁盐,还有铵盐,其中该铵离子,若需要,可携带1至4个C1-C4-烷基,羟基-C1-C4-烷基取代基和/或1个苯基或苄基取代基,优选二异丙基铵,四甲基铵,四丁基铵,三甲基苄基铵及三甲基-(2-羟基乙基)铵盐,此外还有鏻盐,锍盐,如优选三-(C1-C4-烷基)锍盐,及氧化锍盐,如优选三-(C1-C4-烷基)氧化锍盐。
对取代基R1及R4至R19提及或作为在苯基环上的基团提及的有机分子部分是个别组群成员的个别名单的集合词。全部烃链,即,全部烷基,卤代烷基,苯基烷基,亚烷基,烷氧基,卤代烷氧基,苯基烷氧基,烷基亚磺酰基,烷基磺酰基,羟基羰基烷基,链烯基,炔基,链烯氧基及炔氧基部分可以是直链或支链。卤代取代基优选携带1至5个相同或不同的卤素原子。
在每一情况中该术语卤素代表氟,氯,溴或碘,特别是氟或氯。
其它意义的例子是:
-C1-C6-烷基:C1-C4-烷基如CH3,C2H5,CH2-C2H5,CH(CH3)2,正丁基,CH(CH3)-C2H5,CH2-CH(CH3)2及C(CH3)3,或例如,正戊基,1-甲基丁基,2-甲基丁基,3-甲基丁基,2,2-二甲基丙基,1-乙基丙基,正己基,1,1-二甲基丙基,1,2-二甲基丙基,1-甲基戊基,2-甲基戊基,3-甲基戊基,4-甲基戊基,1,1-二甲基丁基,1,2-二甲基丁基,1,3-二甲基丁基,2,2-二甲基丁基,2,3-二甲基丁基,3,3-二甲基丁基,1-乙基丁基,2-乙基丁基,1,1,2-三甲基丙基,1,2,2-三甲基丙基,1-乙基-1-甲基丙基或1-乙基-2-甲基丙基,特别是CH3,C2H5,CH2-C2H5,CH(CH3)2,正丁基,C(CH3)3,正戊基或正己基;
-C1-C6-卤代烷基:部分或全部被氟,氯,溴和/或碘取代的上述C1-C6-烷基,即,例如CH2F,CHF2,CF3,CH2Cl,CHCl2,CCl3,CHFC,CFCl2,CF2Cl,CF2Br,1-氟乙基,2-氟乙基,2-氯乙基,2-溴乙基,2-碘乙基,2,2-二氟乙基,2,2,2-三氟乙基,2-氯-2-氟乙基,2-氯-2,2-二氟乙基,2,2-二氯-2-氟-乙基,1,2-二氯乙基,2,2,2-三氯乙基,C2F5,2-氟丙基,3-氟丙基,2,2-二氟丙基,2,3-二氟丙基,2-氯丙基,3-氯丙基,2,3-二氯丙基,2-溴丙基,3-溴丙基,3,3,3-三溴丙基,3,3,3-三氯丙基,CH2-C2F5,CF2-C2F5,1-(氟甲基)-2-氟乙基,1-(氯甲基)-2-氯乙基,1-(溴甲基)-2-溴乙基,4-氟丁基,4-氯丁基,4-溴丁基,九氟丁基,5-氟戊基,5-氯戊基,5-溴戊基,5-碘戊基,5,5,5-三氯戊基,十一氟戊基,6-氯己基,6-氯己基,6-溴己基,6-碘己基,6,6,6-三氯己基或十二氟己基,特别是CH2F,CHF2,CF3,CH2Cl,2-氟乙基,2-氯乙基,1,2-二氯乙基,2,2,2-三氟乙基或C2F5;
-苯基-C1-C6-烷基:例如苄基,1-苯基乙基,2-苯基乙基,1-苯基丙-1-基,2-苯基丙-1-基,3-苯基丙-1-基,1-苯基丁-1-基,2-苯基丁-1-基,3-苯基丁-1-基,4-苯基丁-1-基,1-苯基丁-2-基,2-苯基丁-2-基,3-苯基丁-2-基,4-苯基丁-2-基,1-(苄基)乙-1-基,1-(苄基)-1-(甲基)乙-1-基,1-(苄基)丙-1-基或2-苯基己-6-基,特别是苄基或2-苯基乙基;
-C3-C6-环烷基:环丙基,环丁基,环戊基或环己基,特别是环戊基或环己基;
-C1-C4-亚烷基:-CH2-,-CH(CH3)-,1,2-亚乙基,1,1-亚丙基,1,2-亚丙基,1,3-亚丙基,-C(CH3)2-,1,1-亚丁基,1,2-亚丁基,1,3-亚丁基,1,4-亚丁基,2,2-亚丁基,2,3-亚丁基,2-甲基-1,1-亚丙基,2-甲基-1,2-亚丙基或2-甲基-1,3-亚丙基,优选亚甲基,1,1-亚乙基,1,2-亚乙基,1,1-亚丙基或2,2-亚丙基;
-C1-C6-烷氧基:例如OCH3,OC2H5,正丙氧基,OCH(CH3)2,正丁氧基,OCH(CH3)-C2H5,OCH2-CH(CH3)2,OC(CH3)3,正戊氧基,1-甲基丁氧基,2-甲基丁氧基,3-甲基丁氧基,1,1-二甲基丙氧基,1,2-二甲基丙氧基,2,2-二甲基丙氧基,1-乙基丙氧基,正己氧基,1-甲基戊氧基,2-甲基戊氧基,3-甲基戊氧基,4-甲基戊氧基,1,1-二甲基丁氧基,1,2-二甲基丁氧基,1,3-二甲基丁氧基,2,2-二甲基丁氧基,2,3-二甲基丁氧基,3,3-二甲基丁氧基,1-乙基丁氧基,2-乙基丁氧基,1,1,2-三甲基丙氧基,1,2,2-三甲基丙氧基,1-乙基-1-甲基丙氧基或1-乙基-2-甲基丙氧基,特别是OCH3,OC2H5,OCH(CH3)2或OC(CH3)3;
-C1-C6-卤代烷氧基:部分或全部被氟,氯,溴和/或碘取代的上述C1-C6-烷氧基,即,例如OCH2F,OCHF2,OCF3,OCH2Cl,OCH(Cl)2,OC(Cl)3,OCHFCl, OCF(Cl)2,OCF2Cl,OCF2Br,1-氟乙氧基,2-氟乙氧基,2-溴乙氧基,2-碘乙氧基,2,2-二氟乙氧基,2,2,2-三氟乙氧基,2-氯-2-氟乙氧基,2-氯-2,2-二氟乙氧基,2,2-二氯-2-氟乙氧基,2,2,2-三氯乙氧基,OC2F5,2-氟丙氧基,3-氟丙氧基,2-氯丙氧基,3-氯丙氧基,2-溴丙氧基,3-溴丙氧基,2,2-二氟丙氧基,2,3-二氟丙氧基,2,3-二氯丙氧基,3,3,3-三氟丙氧基,3,3,3-三氯丙氧基,2,2,3,3,3-五氟丙氧基,OCF2-C2F5,1-(CH2F)-2-氟乙氧基,1-(CH2Cl)-2-氯乙氧基,1-(CH2Br)-2-溴乙氧基,4-氟丁氧基,4-氯丁氧基,4-溴丁氧基,九氟丁氧基,5-氟戊氧基,5-氯戊氧基,5-溴戊氧基,5-碘戊氧基,十一氟戊氧基,6-氟己氧基,6-氯己氧基,6-溴己氧基或十二氟己氧基;
-苯基-C1-C6-烷氧基:例如苯基甲氧基,1-苯基乙氧基,2-苯基乙氧基,1-苯基丙-1-基氧基,2-苯基丙-1-基氧基,3-苯基丙-1-基氧基,1-苯基丁-1-基氧基,2-苯基丁-1-基氧基,3-苯基丁-1-基氧基,4-苯基丁-1-基氧基,1-苯基丁-2-基氧基,2-苯基丁-2-基氧基,3-苯基丁-2-基氧基,4-苯基丁-2-基氧基,1-(苄基)乙-1-基氧基,1-(苄基)-1-(甲基)-乙-1-基氧基,1-(苄基)丙-1-基氧基或2-苯基己-6-基氧基,特别是苄基氧基或2-苯基乙氧基;
-C1-C6-烷氧基-C1-C6-烷基:被上述C1-C6-烷氧基取代的C1-C6-烷基,即,例如CH2OCH3,CH2OC2H5,CH2OCH2-C2H5,CH2OCH(CH3)2,CH2OCH2CH2-C2H5,(1-甲基丙氧基)甲基,(2-甲基丙氧基)甲基,CH2OC(CH3)3,CH2O(CH2)3-C2H5,CH2O(CH2)4-C2H5,CH(CH3)OCH3,CH(CH3)OC2H5,CH2CH2OCH3,CH2CH2 OC2H5,CH2CH2OCH2-C2H5,CH2CH2OCH(CH3)2,CH2CH2OCH2CH2-C2H5,2-(1-甲基丙氧基)乙基,2-(2-甲基丙氧基)乙基,CH2CH2OC(CH3)3,CH2CH2O(CH2)3-C2H5,CH3CH2O(CH2)4-C2H5,2-(OCH3)丙基,2-(OC2H5)丙基,2-(OCH2-C2H5)丙基,2-[OCH(CH3)2]丙基,2-(OCH2CH2-C2H5)丙基,2-(1-甲基丙氧基)丙基,2-(2-甲基丙氧基)丙基,2-[OC(CH3)3]丙基,3-(OCH3)丙基,3-(OC2H5)丙基,3-(OCH2-C2H5)丙基,3-[OCH(CH3)2]丙基,3-(OCH2CH2-C2H5)丙基,3-(1-甲基丙氧基)丙基,3-(2-甲基丙氧基)丙基,3-[OC(CH3)3]丙基,3-(O(CH2)3-C2H5)丙基,3-[O(CH2)4-C2H5]丙基,2-(OCH3)丁基,2-(OC2H5)丁基,2-(OCH2-C2H5)丁基,2-[OCH(CH3)2]丁基,2-(OCH2CH2-C2H5)丁基,2-(1-甲基丙氧基)丁基,2-(2-甲基丙氧基)丁基,2-[OC(CH3)3]丁基,3-(OCH3)丁基,3-(OC2H5)丁基,3-(OCH2-C2H5)丁基,3-[OCH(CH3)2]丁基,3-(OCH2CH2-C2H5)丁基,3-(1-甲基丙氧基)丁基,3-(2-甲基丙氧基)丁基,3-[OC(CH3)3]丁基,4-(OCH3)丁基,4-(OC2H5)丁基,4-(OCH2-C2H5)丁基,4-[OCH(CH3)2]丁基,4-(OCH2CH2-C2H5)丁基,4-(1-甲基丙氧基)丁基,4-(2-甲基丙氧基)丁基,4-[OC(CH3)3]丁基,4-[O(CH2)3-C2H5]丁基,4-[O(CH2)4-C2H5]丁基,5-(OCH3)戊基,5-(OC2H5)戊基,5-(OCH2-C2H5)戊基,5-[OCH(CH3)2]戊基,5-(OCH2CH2-C2H5)戊基,5-(1-甲基丙氧基)戊基,5-(2-甲基丙氧基)戊基,5-[OC(CH3)3]戊基,5-[O(CH2)3-C2H5]戊基,5-[O(CH2)4-C2H5]戊基,6-(OCH3)己基,6-(OC2H5)己基,6-(OCH2-C2H5)己基,6-[OCH(CH3)2]己基,6-(OCH2CH2-C2H5)己基,6-(1-甲基丙氧基)己基,6-(2-甲基丙氧基)己基,6-[OC(CH3)3]己基, 6-[O(CH2)3-C2H5]己基或6-[O(CH2)4-C2H5]己基,特别是CH2OCH3,CH(CH3)OCH3,CH3CH2OCH3或CH(CH3)CH2OCH3;
-羟基羰基-C1-C6-烷基:例如,CH2COOH,CH(CH3)COOH,CH2CH2COOH,1-(COOH)丙-1-基,2-(COOH)丙-1-基,3-(COOH)丙-1-基,1-(COOH)丁-1-基,2-(COOH)丁-1-基,3-(COOH)丁-1-基,4-(COOH)丁-1-基,1-(COOH)丁-2-基,2-(COOH)丁-2-基,3-(COOH)丁-2-基,4-(COOH)丁-2-基,1-(CH2COOH)乙-1-基,1-(CH2COOH)-1-(CH3)乙-1-基,1-(CH2COOH)丙-1-基,5-(COOH)戊-1-基或6-(COOH)己-1-基;
-(C1-C6-烷氧基)羰基:COOCH3,COOC2H5,正丙氧羰基,OCH(CH3)2,正丁氧羰基,1-甲基丙氧羰基,2-甲基丙氧羰基,OC(CH3)3,正戊氧羰基,1-甲基丁氧羰基,2-甲基丁氧羰基,3-甲基丁氧羰基,2,2-二甲基丙氧羰基,1-乙丙氧羰基,正己氧羰基,1,1-二甲基丙氧羰基,1,2-二甲基丙氧羰基,1-甲基戊氧羰基,2-甲基戊氧羰基,3-甲基戊氧羰基,4-甲基戊氧羰基,1,1-二甲基丁氧羰基,1,2-二甲基丁氧羰基,1,3-二甲基丁氧羰基,2,2-二甲基丁氧羰基,2,3-二甲基丁氧羰基,3,3-二甲基丁氧羰基,1-乙基丁氧羰基,2-乙基丁氧羰基,1,1,2-三甲基丙氧羰基,1,2,2-三甲基丙氧羰基,1-C2H5-1-CH3-丙氧羰基,或1-C2H5-2-CH3-丙氧羰基,尤其是COOCH3,COOC2H5或COOC(CH3)3;
-(C1-C6-烷氧基)羰基-C1-C6-烷基:被上述(C3-C6-烷氧基)羰基取代的C1-C6-烷基,即,例如,CH2COOCH3,CH2COOC2H5,CH2COOCH2-C2H5,CH2COOCH(CH3)2,CH2COOCH2CH2-C2H5,(1-甲基丙氧羰基)甲基,(2-甲基丙氧羰基)甲基,CH2COOC(CH3)3,CH2COO(CH2)3-C2H5,CH2COO(CH2)4-C2H5,CH(CH3)COOCH3,CH(CH3)COOC2H5,CH2CH2COOCH3,CH2CH2COOC2H5,CH2CH2COOCH2-C2H5,CH2CH2COOCH(CH3)2,CH2CH2COOCH2CH2-C2H5,2-(1-甲基丙氧羰基)乙基,2-(2-甲基丙氧羰基)乙基,CH2CH2COOC(CH3)3,CH2CH2COO(CH2)3-C2H5,CH2CH2COO(CH2)4-C2H5,2-(COOCH3)丙基,2-(COOC2H5)丙基,2-(COOCH2-C2H5)丙基,2-[COOCH(CH3)2]丙基,2-(COOCH2CH2-C2H5)丙基,2-(1-甲基丙氧羰基)丙基,2-(2-甲基丙氧羰基)丙基,2-[COOC(CH3)3]丙基,3-(COOCH2)丙基,3-(COOC2H5)丙基,3-(COOCH2-C2H5)丙基,3-[COOCH(CH3)2]丙基,3-(COOCH2CH2-C2H5)丙基,3-(1-甲基丙氧羰基)丙基,3-(2-甲基丙氧羰基)丙基,3-[COOC(CH3)3]丙基,3-[COO(CH2)3-C2H5]丙基,3-[COO(CH2)4-C2H5]丙基,2-(COOCH3)丁基,2-(COOC2H5)丁基,2-(COOCH2-C2H5)丁基,2-[COOCH(CH3)2]丁基,2-(COOCH2CH2-C2H5)丁基,2-(1-甲基丙氧羰基)丁基,2-(2-甲基丙氧羰基)丁基,2-[COOC(CH3)3]丁基,3-(COOCH3)丁基,3-(COOC2H5)丁基,3-(COOCH2-C2H5)丁基,3-[COOCH(CH3)2]丁基,3-(COOCH2CH2-C2H5)丁基,3-(1-甲基丙氧羰基)丁基,3-(2-甲基丙氧羰基)丁基,3-[COOC(CH3)3]丁基,4-(COOCH3)丁基,4-(COOC2H5)丁基,4-(COOCH2-C2H5)丁基,4-[COOCH(CH3)2]丁基,4-(COOCH2CH2-C2H5)丁基,4-(1-甲基丙氧羰基)丁基,4-(2-甲基丙氧羰基)丁基,4-[COOC(CH3)3]丁基,4-[COO(CH2)3-C2H5]丁基,4-[COO(CH2)4-C2H5]丁基,5-(COOCH3)戊基,5-(COOC2H5)戊基,5-(COOCH2-C2H5)戊基,5-[COOCH(CH3)2]戊基,5-(COOCH2CH2-C2H5)戊基,5-(1-甲基丙氧羰基)戊基,5-(2-甲基丙氧羰基)戊基,5-[COOC(CH3)3]戊基,5-[COO(CH2)3-C2H5]戊基,5-[COO(CH2)4-C2H5]戊基,6-(COOCH3)己基,6-(COOC2H5)己基,6-(COOCH2-C2H5)己基,6-[COOCH(CH3)2]己基,6-(COOCH2CH2-C2H5)己基,6-(1-甲基丙氧羰基)己基,6-(2-甲基丙氧羰基)己基,6-[COOC(CH3)3]己基,6-[COO(CH2)3-C2H5]己基或6-[COO(CH2)4-C2H5]己基,特别是CH2COOCH3,CH2COOCH(CH3)2或CH(CH3)COOCH3;
-(C1-C6-烷氧基减基-C1-C6-烷氧基:被上述(C1-C6-烷氧基)羰基取代的C1-C6-烷氧基,即,例如,OCH2COOCH3,OCH2COOC2H5,OCH2COOCH2-C2H5,OCH2COOCH(CH3)2,OCH2COOCH2CH2-C2H5,(1-甲基丙氧羰基)甲氧基,(2-甲基丙氧羰基)甲氧基,OCH2COOC(CH3)3,OCH2COO(CH2)3-C2H5,OCH2COO(CH2)4-C2H5,OCH(CH3)COOCH3,OCH(CH3)COOC2H5,OCH2CH2COOCH3,OCH2CH2COOC2H5,OCH2CH2COOCH2-C2H5,OCH2CH2COOCH(CH3)2,OCH2CH2COOCH2CH2-C2H5,2-(1-甲基丙氧羰基)乙氧基,2-(2-甲基丙氧羰基)乙氧基,OCH2CH2COOC(CH3)3,OCH2CH2COO(CH2)3-C2H5,OCH2CH2COO(CH2)4-C2H5,2-(COOCH3)丙氧基,2-(COOC2H5)丙氧基,2-(COOCH2-C2H5)丙氧基,2-[COOCH(CH3)2]丙氧基,2-(COOCH2CH2-C2H5)丙氧基,2-(1-甲基丙氧羰基)丙氧基,2-(2-甲基丙氧羰基)丙氧基,2-[COOC(CH3)3]丙氧基,3-(COOCH3)丙氧基,3-(COOC2H5)丙氧基,3-(COOCH2-C2H5)丙氧基,3-[COOCH(CH3)2]丙氧基,3-(COOCH2CH2-C2H5)丙氧基,3-(1-甲基丙氧羰基)丙氧基,3-(2-甲基丙氧羰基)丙氧基,3-[COOC(CH3)3]丙氧基,3-[COO(CH2)3-C2H5]丙氧基,3-[COO(CH2)4-C2H5]丙氧基,2-(COOCH3)丁氧基,2-(COOC2H5)丁氧基,2-(COOCH2-C2H5)丁氧基,2-[COOCH(CH3)2]丁氧基,2-(COOCH2CH2-C2H5)丁氧基,2-(1-甲基丙氧羰基)丁氧基,2-(2-甲基丙氧羰基)丁氧基,2-[COOC(CH3)3]丁氧基,3-(COOCH3)丁氧基,3-(COOC2H5)丁氧基,3-(COOCH2-C2H5)丁氧基,3-[COOCH(CH3)2]丁氧基,3-(COOCH2CH2-C2H5)丁氧基,3-(1-甲基丙氧羰基)丁氧基,3-(2-甲基丙氧羰基)丁氧基,3-[COOC(CH3)3]丁氧基,4-(COOCH3)丁氧基,4-(COOC2H5)丁氧基,4-(COOCH2-C2H5)丁氧基,4-[COOCH(CH3)2]丁氧基,4-(COOCH2CH2-C2H5)丁氧基,4-(1-甲基丙氧羰基)丁氧基,4-(2-甲基丙氧羰基)丁氧基,4-[COOC(CH3)3]丁氧基,4-[COO(CH2))3-C2H5]丁氧基,4-[COO(CH2)4-C2H5]丁氧基,5-(COOCH3)戊氧基,5-(COOC2H5)戊氧基,5-(COOCH2-C2H5)戊氧基,5-[COOCH(CH3)2]戊氧基,5-(COOCH2CH2-C2H5)戊氧基,5-(1-甲基丙氧羰基)戊氧基,5-(2-甲基丙氧羰基)戊氧基,5-[COOC(CH3)3]戊氧基,5-[COO(CH2)3-C2H5]戊氧基,5-[COO(CH2)4-C2H5]戊氧基,6-(COOCH3)己氧基,6-(COOC2H5)己氧基,6-(COOCH2-C2H5)己氧基,6-[COOCH(CH3)2]己氧基,6-(COOCH2CH2-C2H5)己氧基,6-(1-甲基丙氧羰基)己氧基,6-(2-甲基丙氧羰基)己氧基,6-[COOC(CH3)3]己氧基,6-[COO(CH2)3-C2H5]己氧基或6-[COO(CH2)4-C2H5]己氧基,尤其是OCH2COOCH3,OCH2COOCH(CH3)2,OCH(CH3)COOCH3或OCH2CH2COOCH3;
-C1-C6-烷基亚磺酰基:例如SOCH3,SOC2H5,SOCH2-C2H5,SOCH(CH3)2,正丁基亚磺酰基,SOCH(CH3)-C2H5,SOCH2-CH(CH3)2,SOC(CH3)3,正戊基亚磺酰基,1-甲基丁基亚磺酰基,2-甲基丁基亚磺酰基,3-甲基丁基亚磺酰基,2,2-二甲基丙基亚磺酰基,1-乙基丙基亚磺酰基,正己基亚磺酰基,1,1-二甲基丙基亚磺酰基,1,2-二甲基丙基亚磺酰基,1-甲基戊基亚磺酰基,2-甲基戊基亚磺酰基,3-甲基戊基亚磺酰基,4-甲基戊基亚磺酰基,1,1-二甲基丁基亚磺酰基,1,2-二甲基丁基亚磺酰基,1,3-二甲基丁基亚磺酰基,2,2-二甲基丁基亚磺酰基,2,3-二甲基丁基亚磺酰基,3,3-二甲基丁基亚磺酰基,1-乙基丁基亚磺酰基,2-乙基丁基亚磺酰基,1,1,2-三甲基丙基亚磺酰基,1,2,2-三甲基丙基亚磺酰基,1-乙基-1-甲基丙基亚磺酰基或1-乙基-2-甲基丙基亚磺酰基,特别是SOCH3或SOC2H5;
-C1-C6-烷基磺酰基:例如SO2CH3,SO2C2H5,SO2CH2-C2H5,SO2CH(CH3)2,正丁基磺酰基,SO2CH(CH3)-C2H5,SO2CH2-CH(CH3)2,SO2C(CH3)3,正戊基磺酰基,1-甲基丁基磺酰基,2-甲基丁基磺酰基,3-甲基丁基磺酰基,2,2-二甲基丙基磺酰基,1-乙基丙基磺酰基,正己基磺酰基,1,1-二甲基丙基磺酰基,1,2-二甲基丙基磺酰基,1-甲基戊基磺酰基,2-甲基戊基磺酰基,3-甲基戊基磺酰基,4-甲基戊基磺酰基,1,1-二甲基丁基磺酰基,1,2-二甲基丁基磺酰基,1,3-二甲基丁基磺酰基,2,2-二甲基丁基磺酰基,2,3-二甲基丁基磺酰基,3,3-二甲基丁基磺酰基,1-乙基丁基磺酰基,2-乙基丁基磺酰基,1,1,2-三甲基丙基磺酰基,1,2,2-三甲基丙基磺酰基,1-乙基-1-甲基丙基磺酰基或1-乙基-2-甲基丙基磺酰基,特别是SO2CH3或SO2C2H5;
-C1-C6-卤代烷基磺酰基:部分或全部被氟,氯,溴和/或碘取代的上述C1-C6-烷基磺酰基,即,例如,ClCH2-SO2-,CH(Cl)2-SO2-,C(Cl)3-SO2-,FCH2-SO2-,CHF2-SO2-,CF3-SO2-,氯氟甲基-SO2-,二氯氟甲基-SO2-,氯二氟甲基-SO2-,1-氟乙基-SO2-,2-氟乙基-SO2-,2-氯乙基-SO2-,2-溴乙基-SO2-,2-碘乙基-SO2-,2,2-二氟乙基-SO2-,2,2,2-三氟乙基-SO2-,2-氯-2-氟乙基-SO2-,2-氯-2,2-二氟乙基-SO2-,2,2-二氯-2-氟乙基-SO2-,2,2,2-三氯乙基-SO2-,C2F5-SO2-,2-氟丙基-SO2-,3-氟丙基-SO2-,2,2-二氟丙基-SO2-,2,3-二氟丙基-SO2-,2-氯丙基-SO2-,3-氯丙基-SO2-,2,3-二氯丙基-SO2-,2-溴丙基-SO2-,3-溴丙基-SO2-,3,3,3-三氟丙基-SO2-,3,3,3-三氯丙基-SO2-,2,2,3,3,3-五氟丙基-SO2-,C2F5-CF2-SO2-,1-(氟甲基)-2-氟乙基-SO2-,1-(氯甲基)-2-氯乙基-SO2-, 1-(溴甲基)-2-溴乙基-SO2-,4-氟丁基-SO2-,4-氯丁基-SO2-,4-溴丁基-SO2-,C2F5-CF2-CF2-SO2-,5-氟戊基-SO2-,5-氯戊基-SO2-,5-溴戊基-SO2-,5-碘戊基-SO2-,5,5,5-三氯戊基-SO2-,C2F5-CF2-CF2-CF2-SO2-,6-氟己基-SO2-,6-氯己基-SO2-,6-溴己基-SO2-,6-碘己基-SO2-,6,6,6-三氯己基-SO2-或十二氟己基-SO2-,特别是CF3-SO2-;
-C3-C6-链烯基:例如丙-1-烯-1-基,烯丙基,1-甲乙烯基,正丁烯-1-基,正丁烯-2-基,正丁烯-3-基,1-甲基丙-1-烯-1-基,2-甲基丙-1-烯-1-基,1-甲基丙-2-烯-1-基,2-甲基丙-2-烯-1-基,正戊烯-1-基,正戊烯-2-基,正戊烯-3-基,正戊烯-4-基,1-甲基丁-1-烯-1-基,2-甲基丁-1-烯-1-基,3-甲基丁-1-烯-1-基,1-甲基丁-2-烯-1-基,2-甲基丁-2-烯-1-基,3-甲基丁-2-烯-1-基,1-甲基丁-3-烯-1-基,2-甲基丁-3-烯-1-基,3-甲基丁-3-烯-1-基,1,1-二甲基丙-2-烯-1-基,1,2-二甲基丙-1-烯-1-基,1,2-二甲基丙-2-烯-1-基,1-乙基丙-1-烯-2-基,1-乙基丙-2-烯-1-基,正己-1-烯-1-基,正己-2-烯-1-基,正己-3-烯-1-基,正己-4-烯-1-基,正己-5-烯-1-基,1-甲基戊-1-烯-1-基,2-甲基戊-1-烯-1-基,3-甲基戊-1-烯-1-基,4-甲基戊-1-烯-1-基,1-甲基戊-2-烯-1-基,2-甲基戊-2-烯-1-基,3-甲基戊-2-烯-1-基,4-甲基戊-2-烯-1-基,1-甲基戊-3-烯-1-基,2-甲基戊-3-烯-1-基,3-甲基戊-3-烯-1-基,4-甲基戊-3-烯-1-基,1-甲基戊-4-烯-1-基,2-甲基戊-4-烯-1-基,3-甲基戊-4-烯-1-基,4-甲基戊-4-烯-1-基,1,1-二甲基丁-2-烯-1-基,1,1-二甲基丁-3-烯-1-基,1,2-二甲基丁-1-烯-1-基,1,2-二甲基丁-2-烯-1-基,1,2-二甲基丁-3-烯-1-基,1,3-二甲基丁-1-烯-1-基,1,3-二甲基丁-2-烯-1-基,1,3-二甲基丁-3-烯-1-基,2,2-二甲基丁-3-烯-1-基,2,3-二甲基丁-1-烯-1-基,2,3-二甲基丁-2-烯-1-基,2,3-二甲基丁-3-烯-1-基,3,3-二甲基丁-1-烯-1-基,3,3-二甲基丁-2-烯-1-基,1-乙基丁-1-烯-1-基,1-乙基丁-2-烯-1-基,1-乙基丁-3-烯-1-基,2-乙基丁-1-烯-1-基,2-乙基丁-2-烯-1-基,2-乙基丁-3-烯-1-基,1,1,2-三甲基丙-2-烯-1-基,1-乙基-1-甲基丙-2-烯-1-基,1-乙基-2-甲基丙-2-烯-1-基或1-乙基-2-甲基丙-2-烯-1-基,特别是烯丙基;
-C3-C6-炔基:例如丙-1-炔-1-基,炔丙基,正丁-1-炔-1-基,正丁-1-炔-3-基,正丁-1-炔-4-基,正丁-2-炔-1-基,正戊-1-炔-1-基,正戊-1-炔-3-基,正戊-1-炔-4-基,正戊-1-炔-5-基,正戊-2-炔-1-基,正戊-2-炔-4-基,正戊-2-炔-5-基,3-甲基丁-1-炔-3-基,3-甲基丁-1-炔-4-基,正己-1-炔-1-基,正己-1-炔-3-基,正己-1-炔-4-基,正己-1-炔-5-基,正己-1-炔-6-基,正己-2-炔-1-基,正己-2-炔-4-基,正己-2-炔-5-基,正己-2-炔-6-基,正己-3-炔-1-基,正己-3-炔-2-基,3-甲基戊-1-炔-1-基,3-甲基戊-1-炔-3-基,3-甲基戊-1-炔-4-基,3-甲基戊-1-炔-5-基,4-甲基戊-1-炔-1-基,4-甲基戊-2-炔-4-基或4-甲基戊-2-炔-5-基,特别是炔丙基;
-C3-C6-链烯氧基:例如丙-1-烯-1-基氧基,烯丙氧基,1-甲乙烯氧基,正丁烯-1-基氧基,正丁烯-2-基氧基,正丁烯-3-基氧基,1-甲基丙-1-烯-1-基氧基,2-甲基丙-1-烯-1-基氧基,1-甲基丙-2-烯-1-基氧基,2-甲基丙-2-烯-1-基氧基,正戊烯-1-基氧基,正戊烯-2-基氧基,正戊烯-3-基氧基,正戊烯-4-基氧基,1-甲基丁-1-烯-1-基氧基,2-甲基丁-1-烯-1-基氧基,3-甲基丁-1-烯-1-基氧基,1-甲基丁-2-烯-1-基氧基,2-甲基丁-2-烯-1-基氧基,3-甲基丁-2-烯-1-基氧基,1-甲基丁-3-烯-1-基氧基,2-甲基丁-3-烯-1-基氧基,3-甲基丁-3-烯-1-基氧基,1,1-二甲基丙-2-烯-1-基氧基,1,2-二甲基丙-1-烯-1-基氧基,1,2-二甲基丙-2-烯-1-基氧基,1-乙基丙-1-烯-2-基氧基,1-乙基丙-2-烯-1-基氧基,正己-1-烯-1-基氧基,正己-2-烯-1-基氧基,正己-3-烯-1-基氧基,正己-4-烯-1-基氧基,正己-5-烯-1-基氧基,1-甲基戊-1-烯-1-基氧基,2-甲基戊-1-烯-1-基氧基,3-甲基戊-1-烯-1-基氧基,4-甲基戊-1-烯-1-基氧基,1-甲基戊-2-烯-1-基氧基,2-甲基戊-2-烯-1-基氧基,3-甲基戊-2-烯-1-基氧基,4-甲基戊-2-烯-1-基氧基,1-甲基戊-3-烯-1-基氧基,2-甲基戊-3-烯-1-基氧基,3-甲基戊-3-烯-1-基氧基,4-甲基戊-3-烯-1-基氧基,1-甲基戊-4-烯-1-基氧基,2-甲基戊-4-烯-1-基氧基,3-甲基戊-4-烯-1-基氧基,4-甲基戊-4-烯-1-基氧基,1,1-二甲基丁-2-烯-1-基氧基,1,1-二甲基丁-3-烯-1-基氧基,1,2-二甲基丁-1-烯-1-基氧基,1,2-二甲基丁-2-烯-1-基氧基,1,2-二甲基丁-3-烯-1-基氧基,1,3-二甲基丁-1-烯-1-基氧基,1,3-二甲基丁-2-烯-1-基氧基,1,3-二甲基丁-3-烯-1-基氧基,2,2-二甲基丁-3-烯-1-基氧基,2,3-二甲基丁-1-烯-1-基氧基,2,3-二甲基丁-2-烯-1-基氧基,2,3-二甲基丁-3-烯-1-基氧基,3,3-二甲基丁-1-烯-1-基氧基,3,3-二甲基丁-2-烯-1-基氧基,1-乙基丁-1-烯-1-基氧基,1-乙基丁-2-烯-1-基氧基,1-乙基丁-3-烯-1-基氧基,2-乙基丁-1-烯-1-基氧基,2-乙基丁-2-烯-1-基氧基,2-乙基丁-3-烯-1-基氧基,1,1,2-三甲基丙-2-烯-1-基氧基,1-乙-1-甲基丙-2-烯-1-基氧基,1-乙-2-甲基丙-1-烯-1-基氧基或1-乙-2-甲基丙-2-烯-1-基氧基,特别是烯丙氧基;
-C3-C6-炔氧基:例如丙-1-炔-1-基氧基,炔丙氧基,正丁-1-炔-1-基氧基,正丁-1-炔-3-基氧基,正丁-1-炔-4-基氧基,正丁-2-炔-1-基氧基,正戊-1-炔-1-基氧基,正戊-1-炔-3-基氧基,正戊-1-炔-4-基氧基,正戊-1-炔-5-基氧基,正戊-2-炔-1-基氧基,正戊-2-炔-4-基氧基,正戊-2-炔-5-基氧基,3-甲基丁-1-炔-3-基氧基,3-甲基丁-1-炔-4-基氧基,正己-1-炔-1-基氧基,正己-1-炔-3-基氧基,正己-1-炔-4-基氧基,正己-1-炔-5-基氧基,正己-1-炔-6-基氧基,正己-2-炔-1-基氧基,正己-2-炔-4-基氧基,正己-2-炔-5-基氧基,正己-2-炔-6-基氧基,正己-3-炔-1-基氧基,正己-3-炔-2-基氧基,3-甲基戊-1-炔-1-基氧基,3-甲基戊-1-炔-3-基氧基,3-甲基戊-1-炔-4-基氧基,3-甲基戊-1-炔-5-基氧基,4-甲基戊-1-炔-1-基氧基,4-甲基戊-2-炔-4-基氧基或4-甲基戊-2-炔-5-基氧基,特别是炔丙氧基。
从使用该取代的2-苯基吡啶I作为除草剂和/或作为具有干燥/落叶作用的化合物来看,这些变量优选具有以下意义,在每一情况下以其本身或组合:
n是0;
R1是C1-C6-烷基磺酰基,特别是SO2CH3;
R2是卤素,特别是氯;
R3是氢,氟或氯,特别优选氟或氯,尤其是氟;
R4是氰基或卤素,特别优选氰基或氯,尤其是氯;
R5是氢,硝基,氰基,羟基氨基,C1-C6-烷基(特别是CH3),C1-C6-卤代烷基(特别是卤代甲基),-COCl,-CO-OR6,-CO-O-(C1-C4-亚烷基)-CO-OR6,-O-(C1-C6-亚烷基)-CO-OR6,-O-(C1-C4-亚烷基)-CO-O-(C1-C4-亚烷基)-CO-OR6,-OR9,甲酰基,-CH=N-OR15或NH2,尤其优选-CO-OR6,-CO-O-(C1-C4-亚烷基)-CO-OR6,-O-(C1-C4-亚烷基)-CO-OR6或-OR9;
R6是氢,C1-C6-烷基,C3-C6-链烯基,C3-C6-炔基或C1-C6-烷氧基-C1-C6-烷基;R9是氢,C1-C6-烷基,C3-C6-链烯基或C3-C6-炔基;R15是C1-C6-烷基。非常特别优选的是式Ia(I,其中n=0;R1=甲磺酰基;R2和R4=氯;R3=氟)的化合物,尤其是表1中的化合物:表1
No. | R5 |
Ia.1 | -H |
Ia.2 | -F |
Ia.3 | -Cl |
Ia.4 | -Br |
Ia.5 | -I |
Ia.6 | -CN |
Ia.7 | -CH3 |
Ia.8 | -CH2Cl |
Ia.9 | -CHCl2 |
Ia.10 | -CCl3 |
No. | R5 |
Ia.11 | -CH2Br |
Ia.12 | -CHBr2 |
Ia.13 | -COCl |
Ia.14 | -CO-OH |
Ia.15 | -CO-OCH3 |
Ia.16 | -CO-OC2H5 |
Ia.17 | -CO-OCH2-C2H5 |
Ia.18 | -CO-OCH(CH3)2 |
Ia.19 | -CO-OCH2-CH2-C2H5 |
Ia.20 | -CO-OCH2-CH(CH3)2 |
Ia.21 | -CO-OCH2-CH2-CH2-C2H5 |
Ia.22 | -CO-OCH2-CCl3 |
Ia.23 | -CO-OCH2-CF3 |
Ia.24 | -CO-OCH2-CH=CH2 |
Ia.25 | -CO-OCH2-CH=CH-CH3 |
Ia.26 | -CO-OCH2-CH2-CH=CH2 |
Ia.27 | -CO-OCH(CH3)-CH=CH2 |
Ia.28 | -CO-OCH2-CH2-CH2-CH=CH2 |
Ia.29 | -CO-OCH2-CH=C(CH3)2 |
Ia.30 | -CO-OCH2-C(CH3)=CH-CH3 |
Ia.31 | -CO-OCH2-C≡CH |
Ia.32 | -CO-OCH(CH3)-C≡CH |
Ia.33 | -CO-OCH2-C≡C-CH3 |
Ia.34 | -CO-OCH2-C≡C-C2H5 |
Ia.35 | -CO-O-环丙基 |
Ia.36 | -CO-O-环丁基 |
Ia.37 | -CO-O-环戊基 |
Ia.38 | -CO-O-环己基 |
Ia.39 | -CO-OCH2-CH2-OCH3 |
Ia.40 | -CO-OCH2-CH2-OC2H5 |
Ia.41 | -CO-OCH2-CH2-OCH2-CH2-CH3 |
Ia.42 | -CO-OCH2-CH2-OCH(CH3)2 |
Ia.43 | -CO-NH2 |
Ia.44 | -CO-NH-CH3 |
Ia.45 | -CO-N(CH3)2 |
Ia.46 | -CO-NH-CH2-CO-OH |
No. | R5 |
Ia.47 | -CO-NH-CH2-CO-OCH3 |
Ia.48 | -CO-NH-CH2-CO-OC2H5 |
Ia.49 | -CO-NH-CH2-CO-OCH2-C2H5 |
Ia.50 | -CO-NH-CH2-CO-OCH2-CH2-C2H5 |
Ia.51 | -CO-NH-CH(CH3)-CO-OH |
Ia.52 | -CO-NH-CH(CH3)-CO-OCH3 |
Ia.53 | -CO-NH-CH(CH3)-CO-CO2H5 |
Ia.54 | -CO-NH-CH(CH3)-CO-OCH2-C2H5 |
Ia.55 | -CO-NH-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.56 | -CO-N(CH3)-CH2-CO-OH |
Ia.57 | -CO-N(CH3)-CH2-CO-OCH3 |
Ia.58 | -CO-N(CH3)-CH2-CO-OC2H5 |
Ia.59 | -CO-N(CH3)-CH2-CO-OCH2-C2H5 |
Ia.60 | -CO-N(CH3)-CH2-CO-OCH2-CH2-C2H5 |
Ia.61 | -CO-N(CH3)-CH(CH3)-CO-OH |
Ia.62 | -CO-N(CH3)-CH(CH3)-CO-OCH3 |
Ia.63 | -CO-N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.64 | -CO-N(CH3)-CH(CH3)-CO-OCH2-C2H5 |
Ia.65 | -CO-N(CH3)-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.66 | -CO-OCH2-CO-OH |
Ia.67 | -CO-OCH2-CO-OCH3 |
Ia.68 | -CO-OCH2-CO-OC2H5 |
Ia.69 | -CO-OCH2-CO-OCH2-C2H5 |
Ia.70 | -CO-OCH2-CO-OCH(CH3)2 |
Ia.71 | -CO-OCH2-CO-OCH2-CH2-C2H5 |
Ia.72 | -CO-OCH2-CO-OCH2-CH2-CH(CH3)2 |
Ia.73 | -CO-OCH2-CO-OCH(CH3)-C2H5 |
Ia.74 | -CO-OCH2-CO-OC(CH3)3 |
Ia.75 | -CO-OCH2-CO-OCH2-CH2-CH2-C2H5 |
Ia.76 | -CO-OCH2-CO-OCH2-CH2-CH(CH3)2 |
Ia.77 | -CO-OCH(CH3)-CO-OH |
Ia.78 | -CO-OCH(CH3)-CO-OCH3 |
Ia.79 | -CO-OCH(CH3)-CO-OC2H5 |
Ia.80 | -CO-OCH(CH3)-CO-OCH2-C2H5 |
Ia.81 | -CO-OCH(CH3)-CO-OCH(CH3)2 |
Ia.82 | -CO-OCH(CH3)-CO-OCH2-CH2-C2H5 |
No. | R5 |
Ia.83 | -CO-OCH(CH3)-CO-OCH2-CH(CH3)2 |
Ia.84 | -CO-OCH(CH3)-CO-OCH(CH3)-C2H5 |
Ia.85 | -CO-OCH(CH3)-CO-OC(CH3)3 |
Ia.86 | -CO-OCH(CH3)-CO-OCH2-CH2-CH2-C2H5 |
Ia.87 | -CO-OCH(CH3)-CO-OCH2-CH2-CH(CH3)2 |
Ia.88 | -CO-OCH2-CO-NH2 |
Ia.89 | -CO-OCH2-CO-NH-CH3 |
Ia.90 | -CO-OCH2-CO-N(CH3)2 |
Ia.91 | -CO-OCH2-CO-N(CH3)-CH2-CO-OH |
Ia.92 | -CO-OCH2-CO-N(CH3)-CH2-CO-OCH3 |
Ia.93 | -CO-OCH2-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.94 | -CO-OCH(CH3)-CO-NH2 |
Ia.95 | -CO-OCH(CH3)-CO-NH-CH3 |
Ia.96 | -CO-OCH(CH3)-CO-N(CH3)2 |
Ia.97 | -CO-OCH(CH3)-CO-N(CH3)-CH2-CO-OH |
Ia.98 | -CO-OCH(CH3)-CO-N(CH3)-CH2-CO-OCH3 |
Ia.99 | -CO-OCH(CH3)-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.100 | -OCH2-CHO |
Ia.101 | -OCH2-CO-CH3 |
Ia.102 | -OCH2-CO-C2H5 |
Ia.103 | -OCH2-CO-CH(CH3)2 |
Ia.104 | -OCH2-CO-CH2-C2H5 |
Ia.105 | -OCH2-CO-CH2-CH2-C2H5 |
Ia.106 | -OCH2-CO-CH2-CH(CH3)2 |
Ia.107 | -OCH2-CO-CH(CH3)-C2H5 |
Ia.108 | -OCH2-CO-C(CH3)3 |
Ia.109 | -OCH(CH3)-CO-CH3 |
Ia.110 | -OCH(CH3)-CO-C2H5 |
Ia.111 | -OCH(CH3)-CO-CH2-C2H5 |
Ia.112 | -OCH(CH3)-CO-CH(CH3)2 |
Ia.113 | -OCH(CH3)-CO-CH2-CH2-C2H5 |
Ia.114 | -OCH(CH3)-CO-CH2-CH(CH3)2 |
Ia.115 | -OCH(CH3)-CO-CH(CH3)-C2H5 |
Ia.116 | -OCH(CH3)-CO-C(CH3)3 |
Ia.117 | -OCH2-CO-CH2-Cl |
Ia.118 | -OCH(CH3)-CO-CH2-Cl |
No. | R5 |
Ia.119 | -OCH2-CO-CH2-CH=CH2 |
Ia.120 | -OCH(CH3)-CO-CH2-CH=CH2 |
Ia.121 | -OCH2-CO-CH2-C≡CH |
Ia.122 | -OCH(CH3)-CO-CH2-C≡CH |
Ia.123 | -OCH2-CO-环戊基 |
Ia.124 | -OCH(CH3)-CO-环己基 |
Ia.125 | -OCH2-CO-CH2-OCH3 |
Ia.126 | -OCH(CH3)-CO-CH2-OCH3 |
Ia.127 | -OCH2-CO-CH2-OC2H5 |
Ia.128 | -OCH(CH3)-CO-CH2-OC2H5 |
Ia.129 | -OCH2-CO-CH2-CH2-OCH3 |
Ia.130 | -OCH(CH3)-CO-CH2-CH2-OCH3 |
Ia.131 | -OCH2-CO-CH2-CH2-OC2H5 |
Ia.132 | -OCH(CH3)-CO-CH2-CH2-OC2H5 |
Ia.133 | -SCH2-CHO |
Ia.134 | -SCH2-CO-CH3 |
Ia.135 | -SCH2-CO-C2H5 |
Ia.136 | -SCH2-CO-CH(CH3)2 |
Ia.137 | -SCH2-CO-CH2-C2H5 |
Ia.138 | -SCH(CH3)-CO-CH2-CH2-C2H5 |
Ia.139 | -SCH(CH3)-CO-CH2-CH(CH3)2 |
Ia.140 | -SCH(CH3)-CO-CH(CH3)-C2H5 |
Ia.141 | -SCH(CH3)-CO-C(CH3)3 |
Ia.142 | -SCH2-CO-CH2-CH=CH2 |
Ia.143 | -SCH(CH3)-CO-CH2-CH=CH2 |
Ia.144 | -SCH2-CO-CH2-CH≡CH |
Ia.145 | -SCH(CH3)-CO-CH2-CH≡CH |
Ia.146 | -SCH2-CO-环戊基 |
Ia.147 | -SCH(CH3)-CO-环戊基 |
Ia.148 | -SCH2-CO-环己基 |
Ia.149 | -SCH(CH3)-CO-环己基 |
Ia.150 | -SCH2-CO-CH2-OCH3 |
Ia.151 | -SCH(CH3)-CO-CH2-OCH3 |
Ia.152 | -SCH2-CO-CH2-OC2H5 |
Ia.153 | -SCH(CH3)-CO-CH2-OC2H5 |
Ia.154 | -SCH2-CO-CH2-CH2-OCH3 |
No. | R5 |
Ia.155 | -SCH(CH3)-CO-CH2-CH2-OCH3 |
Ia.156 | -SCH2-CO-CH2-CH2-OC2H5 |
Ia.157 | -SCH(CH3)-CO-CH2-CH2-OC2H5 |
Ia.158 | -OCH2-CO-OH |
Ia.159 | -OCH2-CO-OCH3 |
Ia.160 | -OCH2-CO-OC2H5 |
Ia.161 | -OCH2-CO-OCH2-C2H5 |
Ia.162 | -OCH2-CO-OCH(CH3)2 |
Ia.163 | -OCH2-CO-OCH2-CH2-C2H5 |
Ia.164 | -OCH2-CO-OCH2-CH(CH3)2 |
Ia.165 | -OCH2-CO-OC(CH3)3 |
Ia.166 | -OCH2-CO-OCH2-CH2-CH2-C2H5 |
Ia.167 | -OCH2-CO-OCH2-CH2-CH(CH3)2 |
Ia.168 | -OCH(CH3)-CO-OH |
Ia.169 | -OCH(CH3)-CO-OCH3 |
Ia.170 | -OCH(CH3)-CO-OC2H5 |
Ia.171 | -OCH(CH3)-CO-OCH2-OC2H5 |
Ia.172 | -OCH(CH3)-CO-OCH(CH3)2 |
Ia.173 | -OCH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.174 | -OCH(CH3)-CO-OCH2-CH(CH3)2 |
Ia.175 | -OCH(CH3)-CO-OC(CH3)3 |
Ia.176 | -OCH(CH3)-CO-OCH2-CH2-CH2-C2H5 |
Ia.177 | -OCH(CH3)-CO-OCH2-CH2-CH(CH3)2 |
Ia.178 | -SCH2-CO-OH |
Ia.179 | -SCH2-CO-OCH3 |
Ia.180 | -SCH2-CO-OC2H5 |
Ia.181 | -SCH2-CO-OCH2-C2H5 |
Ia.182 | -SCH2-CO-OCH(CH3)2 |
Ia.183 | -SCH2-CO-OCH2-CH2-C2H5 |
Ia.184 | -SCH2-CO-OCH2-CH(CH3)2 |
Ia.185 | -SCH2-CO-OC(CH3)3 |
Ia.186 | -SCH2-CO-OCH2-CH2-CH2-C2H5 |
Ia.187 | -SCH2-CO-OCH2-CH2-CH(CH3)2 |
Ia.188 | -SCH(CH3)-CO-OH |
Ia.189 | -SCH(CH3)-CO-OCH3 |
Ia.190 | -SCH(CH3)-CO-OC2H5 |
No. | R5 |
Ia.191 | -SCH(CH3)-CO-OCH2-C2H5 |
Ia.192 | -SCH(CH3)-CO-OCH(CH3)2 |
Ia.193 | -SCH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.194 | -SCH(CH3)-CO-OCH2-CH(CH3)2 |
Ia.195 | -SCH(CH3)-CO-OC(CH3)3 |
Ia.196 | -SCH(CH3)-CO-OCH2-CH2-CH2-C2H5 |
Ia.197 | -SCH(CH3)-CO-OCH2-CH2-CH(CH3)2 |
Ia.198 | -OCH2-CO-OCH2-CO-OH |
Ia.199 | -OCH2-CO-OCH2-CO-OCH3 |
Ia.200 | -OCH2-CO-OCH2-CO-OC2H5 |
Ia.201 | -OCH2-CO-OCH2-CO-OCH2-C2H5 |
Ia.202 | -OCH2-CO-OCH2-CO-OCH(CH3)2 |
Ia.203 | -OCH2-CO-OCH2-CO-OCH2-CH2-C2H5 |
Ia.204 | -OCH2-CO-OCH2-CO-OCH2-CH(CH3)2 |
Ia.205 | -OCH2-CO-OCH2-CO-OCH(CH3)-C2H5 |
Ia.206 | -OCH2-CO-OCH2-CO-OC(CH3)3 |
Ia.207 | I>-OCH2-CO-OCH(CH3)-CO-OH |
Ia.208 | -OCH2-CO2-CH(CH3)-CO-OCH3 |
Ia.209 | -OCH2-CO-OCH(CH3)-CO-OC2H5 |
Ia.210 | -OCH2-CO-OCH(CH3)-CO-OCH2-C2H5 |
Ia.211 | -OCH2-CO-OCH(CH3)-CO-OCH(CH3)2 |
Ia.212 | -OCH2-CO-OCH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.213 | -OCH2-CO-OCH(CH3)-CO-OCH2-CH(CH3)2 |
Ia.214 | -OCH2-CO-OCH(CH3)-CO-OCH(CH3)-C2H5 |
Ia.215 | -OCH2-CO-OCH(CH3)-CO-OC(CH3)3 |
Ia.216 | -OCH(CH3)-CO-OCH2-CO-OH |
Ia.217 | -OCH(CH3)-CO-OCH2-CO-OCH3 |
Ia.218 | -OCH(CH3)-CO-OCH2-CO-OC2H5 |
Ia.219 | -OCH(CH3)-CO-OCH2-CO-OCH2-C2H5 |
Ia.220 | -OCH(CH3)-CO-OCH2-CO-OCH(CH3)2 |
Ia.221 | -OCH(CH3)-CO-OCH2-CO-OCH2-CH2-C2H5 |
Ia.222 | -OCH(CH3)-CO-OCH2-CO-OCH2-CH(CH3)2 |
Ia.223 | -OCH(CH3)-CO-OCH2-CO-OCH(CH3)-C2H5 |
Ia.224 | -OCH(CH3)-CO-OCH2-CO-OC(CH3)3 |
Ia.225 | -OCH(CH3)-CO-OCH(CH3)-CO-OH |
Ia.226 | -OCH(CH3)-CO-OCH(CH3)-CO-OCH3 |
No. | R5 |
Ia.227 | -OCH(CH3)-CO-OCH(CH3)-CO-OC2H5 |
Ia.228 | -OCH(CH3)-CO-OCH(CH3)-CO-OCH2-C2H5 |
Ia.229 | -OCH(CH3)-CO-OCH(CH3)-CO-OCH(CH3)2 |
Ia.230 | -OCH(CH3)-CO-OCH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.231 | -OCH(CH3)-CO-OCH(CH3)-CO-OCH2-CH(CH3)2 |
Ia.232 | -OCH(CH3)-CO-OCH(CH3)-CO-OCH(CH3)-C2H5 |
Ia.233 | -OCH(CH3)-CO-OCH(CH3)-CO-OC(CH3)3 |
Ia.234 | -SCH2-CO-OCH2-CO-OH |
Ia.235 | -SCH2-CO-OCH2-CO-OCH3 |
Ia.236 | -SCH2-CO-OCH2-CO-OC2H5 |
Ia.237 | -SCH2-CO-OCH2-CO-OCH2-C2H5 |
Ia.238 | -SCH2-CO-OCH2-CO-OCH(CH3)2 |
Ia.239 | -SCH2-CO-OCH2-CO-OCH2-CH2-C2H5 |
Ia.240 | -SCH2-CO-OCH2-CO-OCH2-CH(CH3)2 |
Ia.241 | -SCH2-CO-OCH2-CO-OCH(CH3)-C2H5 |
Ia.242 | -SCH2-CO-OCH2-CO-OC(CH3)3 |
Ia.243 | -SCH2-CO-OCH(CH3)-CO-OH |
Ia.244 | -SCH2-CO-OCH(CH3)-CO-OCH3 |
Ia.245 | -SCH2-CO-OCH(CH3)-CO-OC2H5 |
Ia.246 | -SCH2-CO-OCH(CH3)-CO-OCH2-C2H5 |
Ia.247 | -SCH2-CO-OCH(CH3)-CO-OCH(CH3)2 |
Ia.248 | -SCH2-CO-OCH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.249 | -SCH2-CO-OCH(CH3)-CO-OCH2-CH(CH3)2 |
Ia.250 | -SCH2-CO-OCH(CH3)-CO-OCH(CH3)-C2H5 |
Ia.251 | -SCH2-CO-OCH(CH3)-CO-OC(CH3)3 |
Ia.252 | -SCH(CH3)-CO-OCH2-CO-OH |
Ia.253 | -SCH(CH3)-CO-OCH2-CO-OCH3 |
Ia.254 | -SCH(CH3)-CO-OCH2-CO-OC2H5 |
Ia.255 | -SCH(CH3)-CO-OCH2-CO-OCH2-C2H5 |
Ia.256 | -SCH(CH3)-CO-OCH2-CO-OCH(CH3)2 |
Ia.257 | -SCH(CH3)-CO-OCH2-CO-OCH2-CH2-C2H5 |
Ia.258 | -SCH(CH3)-CO-OCH2-CO-OCH2-CH(CH3)2 |
Ia.259 | -SCH(CH3)-CO-OCH2-CO-OCH(CH3)-C2H5 |
Ia.260 | -SCH(CH3)-CO-OCH2-CO-OC(CH3)3 |
Ia.261 | -SCH(CH3)-CO-OCH(CH3)-CO-OH |
Ia.262 | -SCH(CH3)-CO-OCH(CH3)-CO-OCH3 |
No. | R5 |
Ia.263 | -SCH(CH3)-CO-OCH(CH3)-CO-OC2H5 |
Ia.264 | -SCH(CH3)-CO-OCH(CH3)-CO-OCH2-C2H5 |
Ia.265 | -SCH(CH3)-CO-OCH(CH3)-CO-OCH(CH3)2 |
Ia.266 | -SCH(CH3)-CO-OCH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.267 | -SCH(CH3)-CO-OCH(CH3)-CO-OCH2-CH(CH3)2 |
Ia.268 | -SCH(CH3)-CO-OCH(CH3)-CO-OCH(CH3)-C2H5 |
Ia.269 | -SCH(CH3)-CO-OCH(CH3)-CO-OC(CH3)3 |
Ia.270 | -OCH2-CO-NH2 |
Ia.271 | -OCH2-CO-NH-CH3 |
Ia.272 | -OCH2-CO-N(CH3)2 |
Ia.273 | -OCH2-CO-NH-CH2-CO-OH |
Ia.274 | -OCH2-CO-NH-CH2-CO-OCH3 |
Ia.275 | -OCH2-CO-NH-CH2-CO-OC2H5 |
Ia.276 | -OCH2-CO-NH-CH2-CO-OCH2-C2H5 |
Ia.277 | -OCH2-CO-NH-CH2-CO-OCH2-CH2-C2H5 |
Ia.278 | -OCH2-CO-NH-CH(CH3)-CO-OH |
Ia.279 | -OCH2-CO-NH-CH(CH3)-CO-OCH3 |
Ia.280 | -OCH2-CO-NH-CH(CH3)-CO-OC2H5 |
Ia.281 | -OCH2-CO-NH-CH(CH3)-CO-OCH2-C2H5 |
Ia.282 | -OCH2-CO-NH-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.283 | -OCH2-CO-N(CH3)-CH2-CO-OH |
Ia.284 | -OCH2-CO-N(CH3)-CH2-CO-OCH3 |
Ia.285 | -OCH2-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.286 | -OCH2-CO-N(CH3)-CH2-CO-OCH2-C2H5 |
Ia.287 | -OCH2-CO-N(CH3)-CH2-CO-OCH2-CH2-C2H5 |
Ia.288 | -OCH2-CO-N(CH3)-CH(CH3)-CO-OH |
Ia.289 | -OCH2-CO-N(CH3)-CH(CH3)-CO-OCH3 |
Ia.290 | -OCH2-CO-N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.291 | -OCH2-CO-N(CH3)-CH(CH3)-CO-OCH2-C2H5 |
Ia.292 | -OCH2-CO-N(CH3)-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.293 | -OCH(CH3)-CO-NH2 |
Ia.294 | -OCH(CH3)-CO-NH-CH3 |
Ia.295 | -OCH(CH3)-CO-N(CH3)2 |
Ia.296 | -OCH(CH3)-CO-NH-CH2-CO-OH |
Ia.297 | -OCH(CH3)-CO-NH-CH2-CO-OCH3 |
Ia.298 | -OCH(CH3)-CO-NH-CH2-CO-OC2H5 |
No. | R5 |
Ia.299 | -OCH(CH3)-CO-NH-CH2-CO-OCH2-C2H5 |
Ia.300 | -OCH(CH3)-CO-NH-CH2-CO-OCH2-CH2-C2H5 |
Ia.301 | -OCH(CH3)-CO-NH-CH(CH3)-CO-OH |
Ia.302 | -OCH(CH3)-CO-NH-CH(CH3)-CO-OCH3 |
Ia.303 | -OCH(CH3)-CO-NH-CH(CH3)-CO-OC2H5 |
Ia.304 | -OCH(CH3)-CO-NH-CH(CH3)-CO-OCH2-C2H5 |
Ia.305 | -OCH(CH3)-CO-NH-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.306 | -OCH(CH3)-CO-N(CH3)-CH2-CO-OH |
Ia.307 | -OCH(CH3)-CO-N(CH3)-CH2-CO-OCH3 |
Ia.308 | -OCH(CH3)-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.309 | -OCH(CH3)-CO-N(CH3)-CH2-CO-OCH2-C2H5 |
Ia.310 | -OCH(CH3)-CO-N(CH3)-CH2-CO-OCH2-CH2-C2H5 |
Ia.311 | -OCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OH |
Ia.312 | -OCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OCH3 |
Ia.313 | -OCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.314 | -OCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OCH2-C2H5 |
Ia.315 | -OCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.316 | -SCH2-CO-NH2 |
Ia.317 | -SCH2-CO-NH-CH3 |
Ia.318 | -SCH2-CO-N(CH3)2 |
Ia.319 | -SCH2-CO-NH-CH2-CO-OH |
Ia.320 | -SCH2-CO-NH-CH2-CO-OCH3 |
Ia.321 | -SCH2-CO-NH-CH2-CO-OC2H5 |
Ia.322 | -SCH2-CO-NH-CH2-CO-OCH2-C2H5 |
Ia.323 | -SCH2-CO-NH-CH2-CO-OCH2-CH2-C2H5 |
Ia.324 | -SCH2-CO-NH-CH(CH3)-CO-OH |
Ia.325 | -SCH2-CO-NH-CH(CH3)-CO-OCH3 |
Ia.326 | -SCH2-CO-NH-CH(CH3)-CO-OC2H5 |
Ia.327 | -SCH2-CO-NH-CH(CH3)-CO-OCH2-C2H5 |
Ia.328 | -SCH2-CO-NH-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.329 | -SCH2-CO-N(CH3)-CH2-CO-OH |
Ia.330 | -SCH2-CO-N(CH3)-CH2-CO-OCH3 |
Ia.331 | -SCH2-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.332 | -SCH2-CO-N(CH3))-CH2-CO-OCH2-C2H5 |
Ia.333 | -SCH2-CO-N(CH3)-CH2-CO-OCH2-CH2-C2H5 |
Ia.334 | -SCH2-CO-N(CH3)-CH(CH3)-CO-OH |
No. | R5 |
Ia.335 | -SCH2-CO-N(CH3)-CH(CH3)-CO-OCH3 |
Ia.336 | -SCH2-CO-N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.337 | -SCH2-CO-N(CH3)-CH(CH3)-CO-OCH2-C2H5 |
Ia.338 | -SCH2-CO-N(CH3)-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.339 | -SCH(CH3)-CO-NH2 |
Ia.340 | -SCH(CH3)-CO-NH-CH3 |
Ia.341 | -SCH(CH3)-CO-N(CH3)2 |
Ia.342 | -SCH(CH3)-CO-NH-CH2-CO-OH |
Ia.343 | -SCH(CH3)-CO-NH-CH2-CO-OCH3 |
Ia.344 | -SCH(CH3)-CO-NH-CH2-CO-OC2H5 |
Ia.345 | -SCH(CH3)-CO-NH-CH2-CO-OCH2-C2H5 |
Ia.346 | -SCH(CH3)-CO-NH-CH2-CO-OCH2-CH2-C2H5 |
Ia.347 | -SCH(CH3)-CO-NH-CH(CH3)-CO-OH |
Ia.348 | -SCH(CH3)-CO-NH-CH(CH3)-CO-OCH3 |
Ia.349 | -SCH(CH3)-CO-NH-CH(CH3)-CO-OC2H5 |
Ia.350 | -SCH(CH3)-CO-NH-CH(CH3)-CO-OCH2-C2H5 |
Ia.351 | -SCH(CH3)-CO-NH-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.352 | -SCH(CH3)-CO-N(CH3)-CH2-CO-OH |
Ia.353 | -SCH(CH3)-CO-N(CH3)-CH2-CO-OCH3 |
Ia.354 | -SCH(CH3)-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.355 | -SCH(CH3)-CO-N(CH3)-CH2-CO-OCH2-C2H5 |
Ia.356 | -SCH(CH3)-CO-N(CH3)-CH2-CO-OCH2-CH2-C2H5 |
Ia.357 | -SCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OH |
Ia.358 | -SCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OCH3 |
Ia.359 | -SCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.360 | -SCH(CH3)-CO-N(CH3)-CH(CH3)-CO-OCH2-C2H5 |
Ia.361 | -SCH(CHH3)-CO-N(CH3)-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.362 | -OH |
Ia.363 | -OCH3 |
Ia.364 | -OC2H5 |
Ia.365 | -OCH2-C2H5 |
Ia.366 | -OCH(CH3)2 |
Ia.367 | -OCH2-CH2-C2H5 |
Ia.368 | -OCH(CH3)-C2H5 |
Ia.369 | -OCH2-CH(CH3)2 |
Ia.370 | -OCH2-CH2-CH2-C2H5 |
No. | R5 |
Ia.371 | -OCH2-CH2-CH(CH3)-CH3 |
Ia.372 | -OCH2-CF3 |
Ia.373 | -OCHF2 |
Ia.374 | -OCH2-CH=CH2 |
Ia.375 | -OCH2-CH=CH-CH3 |
Ia.376 | -OCH2-CH(CH3)=CH2 |
Ia.377 | -OCH(CH3)-CH=CH2 |
Ia.378 | -OCH2-CH=CH-C2H5 |
Ia.379 | -OCH2-CH2-CH3=CH-CH3 |
Ia.380 | -OCH2-CH2-CH2-CH=CH2 |
Ia.381 | -OCH2-C≡CH |
Ia.382 | -OCH(CH3)-C≡CH |
Ia.383 | -OCH2-C≡C-CH3 |
Ia.384 | -OCH2-C≡C-C2H5 |
Ia.385 | 环丙氧基 |
Ia.386 | 环丁氧基 |
Ia.387 | 环戊氧基 |
Ia.388 | 环己氧基 |
Ia.389 | -OCH2-CH2-OCH3 |
Ia.390 | -OCH2-CH2-OC2H5 |
Ia.391 | -OCH2-CH2-OCH2-C2H5 |
Ia.392 | -OCH2-CH2-OCH(CH3)2 |
Ia.393 | -SH |
Ia.394 | -SCH3 |
Ia.395 | -SC2H5 |
Ia.396 | -SCH2-C2H5 |
Ia.397 | -SCH(CH3)2 |
Ia.398 | -SCH2-CH2-C2H5 |
Ia.399 | -SCH(CH3)-C2H5 |
Ia.400 | -SCH2-CH(CH3)2 |
Ia.401 | -SCH2-CH2-CH2-C2H5 |
Ia.402 | -SCH2-CH2-CH(CH3)-CH3 |
Ia.403 | -SCH2-CF3 |
Ia.404 | -SCHF2 |
Ia.405 | -SCH2-CH=CH2 |
Ia.406 | -SCH2-CH=CH-CH3 |
No. | R5 |
Ia.407 | -SCH2-CH(CH3)=CH2 |
Ia.408 | -SCH(CH3)-CH=CH2 |
Ia.409 | -SCH2-CH=CH-C2H5 |
Ia.410 | -SCH2-CH2-CH=CH-CH3 |
Ia.411 | -SCH2-CH2-CH2-CH=CH2 |
Ia.412 | -SCH2-C≡CH |
Ia.413 | -SCH(CH3)-C≡CH |
Ia.414 | -SCH2-C≡C-CH3 |
Ia.415 | -SCH2-C≡C-C2H5 |
Ia.416 | 环丙硫基 |
Ia.417 | 环丁硫基 |
Ia.418 | 环戊硫基 |
Ia.419 | 环己硫基 |
Ia.420 | -SCH2-CH2-OCH3 |
Ia.421 | -SCH2-CH2-OC2H5 |
Ia.422 | -SCH2-CH2-OCH2-C2H5 |
Ia.423 | -SCH2-CH2-OCH(CH3)2 |
Ia.424 | -CH=CH2-CO-OH |
Ia.425 | -CH=CH2-CO-OCH3 |
Ia.426 | -CH=CH2-CO-OC2H5 |
Ia.427 | -CH=C2-CO-OCH2-C2H5 |
Ia.428 | -CH=CH2-CO-OCH2-CH2-C2H5 |
Ia.429 | -CH=CH(Cl)-CO-OH |
Ia.430 | -CH=CH(Cl)-CO-OCH3 |
Ia.431 | -CH=CH(Cl)-CO-OC2H5 |
Ia.432 | -CH=CH(Cl)-CO-OCH2-C2H5 |
Ia.433 | -CH=CH(Cl)-CO-OCH2-CH2-C2H5 |
Ia.434 | -CH=CH(CH3)-CO-OH |
Ia.435 | -CH=CH(CH3)-CO-OCH3 |
Ia.436 | -CH=CH(CH3)-CO-OC2H5 |
Ia.437 | -CH=CH(CH3)-CO-OCH2-C2H5 |
Ia.438 | -CH=CIH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.439 | -CH=CH-CO-NH2 |
Ia.440 | -CH=CH-CO-NH-CH3 |
Ia.441 | -CH=CH-CO-N(CH3)2 |
Ia.442 | -CH=CH-CO-NH-CH2-CO-OH |
No. | R5 |
Ia.443 | -CH=CH-CO-NH-CH2-CO-OCH3 |
Ia.444 | -CH=CH-CO-NH-CH2-CO-OC2H5 |
Ia.445 | -CH=CH-CO-NH-CH(CH3)-CO-OH |
Ia.446 | -CH=CH-CO-NH-CH(CH3)-CO-OCH3 |
Ia.447 | -CH=CH-CO-NH-CH(CH3)-CO-OC2H5 |
Ia.448 | -CH=CH-CO-N(CH3)-CH2-CO-OH |
Ia.449 | -CH=CH-CO-N(CH3)-CH2-CO-OCH3 |
Ia.450 | -CH=CH-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.451 | -CH=CH-CO-N(CH3)-CH(CH3)-CO-OH |
Ia.452 | -CH=CH-CO-N(CH3)-CH(CH3)-CO-OCH3 |
Ia.453 | -CH=CH-CO-N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.454 | -CH=C(Cl)-CO-NH-CH(CH3)-CO-OH |
Ia.455 | -CH=C(Cl)-CO-NH-CH(CH3)-CO-OCH3 |
Ia.456 | -CH=C(Cl)-CO-NH-CH(CH3)-CO-OC2H5 |
Ia.457 | -CH=C(Cl)-CO-N(CH3)-CH2-CO-OH |
Ia.458 | -CH=C(Cl)-CO-N(CH3)-CH2-CO-OCH3 |
Ia.459 | -CH=C(Cl)-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.460 | -CH=C(Cl)-CO-N(CH3)-CH(CH3)-CO-OH |
Ia.461 | -CH=C(Cl)-CO-N(CH3)-CH(CH3)-CO-OCH3 |
Ia.462 | -CH=C(Cl)-CO-N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.463 | -CHO |
Ia.464 | -CO-CH3 |
Ia.465 | -CO-C2H5 |
Ia.466 | -CO-CH2-C2H5 |
Ia.467 | -CO-CH(CH3)2 |
Ia.468 | -CO-CH2-CH2-C2H5 |
Ia.469 | -CO-CH2-CH(CH3)-CH3 |
Ia.470 | -CO-CH(CH3)-C2H5 |
Ia.471 | -CO-CH2-Cl |
Ia.472 | -CO-CH2-Br |
Ia.473 | -CO-CHC2 |
Ia.474 | -CO-CHBr2 |
Ia.475 | -CO-CCl3 |
Ia.476 | -CO-CF3 |
Ia.477 | -CH=C(CH3)-CO-NH2 |
Ia.478 | -CH=C(CH3)-CO-NH-CH3 |
No. | R5 |
Ia.479 | -CH=C(CH3)-CO-N(CH3)2 |
Ia.480 | -CH=C(CH3)-CO-NH-CH2-CO-OH |
Ia.481 | -CH=C(CH3)-CO-MH-CH2-CO-OCH3 |
Ia.482 | -CH=C(CH3)-CO-NH-CH2-CO-OC2H5 |
Ia.483 | -CH=C(CH3)-CO-NH-CH(CH3)-CO-OH |
Ia.484 | -CH=C(CH3)-CO-NH-CH(CH3)-CO-OCH3 |
Ia.485 | -CH=C(CH3)-CO-NH-CH(CH3)-CO-OC2H5 |
Ia.486 | -CH=C(CH3)-CO-N(CH3)-CH2-CO-OH |
Ia.487 | -CH=C(CH3)-CO-N(CH3)-CH2-CO-OCH3 |
Ia.488 | -CH=C(CH3)-CO-N(CH3)-CH2-CO-OC2H5 |
Ia.489 | -CH=C(CH3)-CO-N(CH3)-CH(CH3)-CO-OH |
Ia.490 | -CH=C(CH3)-CO-N(CH3)-CH(CH3)-CO-OCH3 |
Ia.491 | -CH=C(CH3)-CO-N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.492 | -CH=C(Cl)-CO-NH2 |
Ia.493 | -CH=C(Cl)-CO-NH-CH3 |
Ia.494 | -CH=C(Cl)-CO-N(CH3)2 |
Ia.495 | -CH=C(Cl)-CO-NH-CH2-CO-OH |
Ia.496 | -CH=C(Cl)-CO-NH-CH2-CO-OCH3 |
Ia.497 | -CH=C(Cl)-CO-NH-CH2-CO-OC2H5 |
Ia.498 | -CO-CH2-CH=CH2 |
Ia.499 | -CO-CH2-CH=CH-CH3 |
Ia.500 | -CO-CH2-CH2-CH=CH2 |
Ia.501 | -CO-CH2-C≡CH |
Ia.502 | -CO-CH(CH3)-C≡CH |
Ia.503 | -CO-CH2-C≡C-CH3 |
Ia.504 | 环丙羰基 |
Ia.505 | 环丁羰基 |
Ia.506 | 环戊羰基 |
Ia.507 | 环己羰基 |
Ia.508 | -CO-CH2-OCH3 |
Ia.509 | -CO-CH2-OC2H5 |
Ia.510 | -CO-CH2-CH2-OCH3 |
Ia.511 | -CO-CH2-CH2-OC2H5 |
Ia.512 | 1,3-二氧戊环-2-基 |
Ia.513 | 4-(CH3)-1,3-二氧戊环-2-基 |
Ia.514 | 4,5-(CH3)2-1,3-二氧戊环-2-基 |
No. | R5 |
Ia.547 | -CH=N-OCH(CH3)2 |
Ia.548 | -CH=N-OCH2-CH2-C2H5 |
Ia.549 | -CH=N-OCH2-CH(CH3)2 |
Ia.550 | -CH=N-OCH(CH3)-C2H5 |
Ia.551 | -CH=N-OC(CH3)3 |
Ia.552 | -CH=N-OCH2-CH2-CH2-C2H5 |
Ia.553 | -CI=N-OCH2-CH2-CH(CH3)2 |
Ia.554 | -CH=N-OCH2-CO-OCH3 |
Ia.555 | -CH=N-OCH2-CO-OC2H5 |
Ia.556 | -CH=N-OCH2-CO-OCH2-C2H5 |
Ia.557 | -CH=N-OCH(CH3)-CO-OCH3 |
Ia.558 | -CH=N-OCH(CH3)-CO-OCH2H5 |
Ia.559 | -CH=N-OCH(CH3)-CO-OCH2-C2H5 |
Ia.560 | -CH(OCH3)2 |
Ia.561 | -CH(OC2H5)2 |
Ia.562 | -CH(OCH2-C2H5)2 |
Ia.563 | -CH(OCH2-CH2-C2H5)2 |
Ia.564 | -NO2 |
Ia.565 | -NH-OH |
Ia.566 | -NH2 |
Ia.567 | -NH-CH3 |
Ia.568 | -N(CH3)2 |
Ia.569 | -NH-CH2-CO-OCH3 |
Ia.570 | -NH-CH2-CO-OC2H5 |
Ia.571 | -NH-CH2-CO-OCH2-C2H5 |
Ia.572 | -NH-CH2-CO-OCH2-CH2-C2H5 |
Ia.573 | -NH-CH(CH3)-CO-OCH3 |
Ia.574 | -NH-CH(CH3)-CO-OC2H5 |
Ia.575 | -NH-CH(CH3)-CO-OCH2-C2H5 |
Ia.576 | -NH-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.577 | -N(CH3)-CH2-CO-OCH3 |
Ia.578 | -N(CH3)-CH2-CO-OC2H5 |
Ia.579 | -N(CH3)-CH2-CO-OCH2-C2H5 |
Ia.580 | -N(CH3)-CH2-CO-OCH2-CH2-C2H5 |
Ia.581 | -N(CH3)-CH(CH3)-CO-OCH3 |
Ia.582 | -N(CH3)-CH(CH3)-CO-OC2H5 |
Ia.583 | -N(CH3)-CH(CH3)-CO-OCH2-C2H5 |
No. | R5 |
Ia.584 | -N(CH3)-CH(CH3)-CO-OCH2-CH2-C2H5 |
Ia.585 | -NH-SO2-CH3 |
Ia.586 | -NH-SO2-C2H5 |
Ia.587 | -NH-SO2-CH2-C2H5 |
Ia.588 | -NH-SO2-CH(CH3)2 |
Ia.589 | -NH-SO2-CH2-CH2-C2H5 |
Ia.590 | -NH-SO2-CH2-CH(CH3)2 |
Ia.591 | -NH-SO2-CH(CH3)-C2H5 |
Ia.592 | -N(CH3)-SO2-CH3 |
Ia.593 | -N(CH3)-SO2-C2H5 |
Ia.594 | -N(CH3)-SO2-CH2-C2H5 |
Ia.595 | -N(CH3)-SO2-CH(CH3)2 |
Ia.596 | -N(CH3)-SO2-CH2-CH2-C2H5 |
Ia.597 | -N(CH3)-SO2-CH2-CH(CH3)2 |
Ia.598 | -NH-CO-CH3 |
Ia.599 | -NH-CO-C2H5 |
Ia.600 | -NH-CO-CH2-C2H5 |
Ia.601 | -NH-CO-CH(CH3)2 |
Ia.602 | -NH-CO-CH2-CH2-C2H5 |
Ia.603 | -NH-CO-CH2-CH(CH3)2 |
Ia.604 | -NH-CO-CH(CH3)-C2H5 |
Ia.605 | -NH-CO-C(CH3)3 |
Ia.606 | -N(CH3)-CO-CH3 |
Ia.607 | -N(CH3)-CO-C2H5 |
Ia.608 | -N(CH3)-CO-CH2-C2H5 |
Ia.609 | -N(CH3)-CO-CH(CH3)2 |
Ia.610 | -N(CH3)-CO-CH2-CH2-C2H5 |
Ia.611 | -N(CH3)-CO-CH2-CH(CH3)2 |
Ia.612 | -N(CH3)-CO-CH(CH3)-C2H5 |
Ia.613 | -N(CH3)-CO-C(CH3)3 |
Ia.614 | -SO2-Cl |
Ia.615 | -SO2-OH |
Ia.616 | -SO2-NH2 |
Ia.617 | -SO2-NH-CH3 |
Ia.618 | -SO2-N(CH3)2 |
Ia.619 | -SO2-NH-CH2-CO-OCH3 |
此外,非常特别优选的是式Ib,Ic,Id,Ie及If的取代2-苯基吡啶,尤其是
-Ib.1至Ib.637的化合物,其与Ia.1至Ia.637对应化合物的不同仅在于R3是氯:
-I.1至If.637的化合物,其与Ia.1至Ia.637对应化合物的不同仅在于R3是氢及R4是氰基:
式I的取代2-苯基吡啶可以由不同途径获得,例如由以下方法之一:
方法A)
式I的取代2-苯基吡啶(其中n是0以及R1和R5不含任何可氧化硫)的氧化作用,以本身所知的方式{参阅,例如,A.Albini & S.Pietra,Heterocyclic N-Oxides,CRC-PressInc.,Boca Raton,USA 1991;H.S.Mosher等人,Org.Synth.Coll. Vol.IV1963,第828页;E.C.Taylor等人,Org.Synth.Coll.Vol.IV1963,第704页;T.W.Bell等人,Org.Synth.69.第226页(1990)}:
在常用于氧化吡啶环的氧化剂中,可以作为例子提及的是过乙酸,三氟过乙酸,过苯甲酸,间-氯过苯甲酸,单过马来酸,单过邻苯二甲酸镁,过硼酸钠,oxon(含过硫酸盐)过钨酸及过氧化氢
适当的溶剂是,例如,水,硫酸,羧酸类诸如乙酸及三氟乙酸,还有卤化烃类,诸如二氯甲烷及三氯甲烷。
通常是在0℃至该反应混合物的沸点温度下进行该氧化作用。
通常基于该起始材料以至少等摩尔量使用该氧化剂。发现一般而言过量的氧化剂尤其有利。
方法B)
M1是B(OH)2,Mg-Cl,Mg-Br,Mg-I,Zn-Cl,Zn-Br,Zn-I,锂,铜或三(C1-C4-烷基)锡,优选B(OH)2,Mg-Cl,Mg-Br,Mg-I,Zn-Cl,Zn-Br或Zn-I。
适当的催化剂特别是钯催化剂,诸如四(三苯基膦)钯(O),氯化双(三苯基膦)钯(II),氯化1,4-双(二苯基膦基)丁烷钯(II),氯化1,2-双(二苯基膦基)乙烷钯(II),乙酸钯(II)+三苯基膦,乙酸钯(II)+三(邻甲苯基)膦或钯/活性炭,及镍催化剂,诸如氯化双(三苯基膦)镍(II),氯化1,3-双(二苯基膦基)丙烷镍(II)或乙酰基丙酮酸镍(II)。
方法C)
5-氨基-2-苯基吡啶V的重氮化作用,该重氮盐与乙酸酐的反应,VI的水解以得5-羟基-2-苯基吡啶VII及VII与R1-L的反应,其中L是一种适当离去基团,诸如氯化物(在R1=C1-C6-烷基磺酰基的情况下)。
此类型的反应通常由例如以下出版物已知(使用亚硝酸异戊酯重氮化氨基吡啶):
C.S.Giam等人,J.Chem.Soc.,Chem.Commun.16,756(1980);T.Yasumitsu等人,J.Org.Chem.46,3564-3567(1981)。
式V的5-氨基-2-苯基吡啶由WO98/07700已知或可以以描述于其中的方式获得。
5-氨基-2-(4-氯-3-甲氧苯基)吡啶及5-氨基-2-(4-氯-3-甲氧苯基)-3-氯吡啶已揭示于WO95/02580。
方法D)
5-羟基-2-苯基吡啶VIII与C1-C6-烷基亚磺酰氯R1-SO-Cl以本身已知的方式{参阅,例如,J.Hendrickson & P.Skipper,Tetrahedron 32,1627(1976);Th.Netscher & H.Prinzbach,Synthesis 8,683-688(1987);Y.F.Zhang等人,Inorg.Chem.31,492-494(1992),M.Jung & T.Lazarova,Tetrahedron Letters37,7-8(1996)}反应:
方法E)
式I的取代2-苯基吡啶(其中R1是C1-C6-烷基亚磺酸基及取代基R5不含任何可氧化硫)的氧化作用,以一种本身已知的方式{参阅,例如,Th.Squires等人,J.Org.Chem.46,2373-2376(1981)及Th.Netscher & H.Prinzbach,Synthesis8,683-688(1987)}:
I(R1=烷基亚磺酰基) I(R1=烷基磺酰基)
就适当的溶剂,反应温度及比率而言,可参照列于方法A)下的细节。除方法A)中所述的氧化剂外,碱金属次卤酸盐,诸如次氯酸钠及次氯酸钾,也适用于此处。
通常可以由上述合成方法之一制备式I的取代2-苯基吡啶。然而,为经济或技术理由,更方便的是从类似的2-苯基吡啶(一个基团的含义不同)制备某些化合物I。
一般而言,可以由例如对应5-氨基吡啶IX(其制备方法参阅J.Med.Chem.16,319-327(1973))的重氮化作用-优选使用一种亚硝酸酯诸如亚硝酸叔丁酯及亚硝酸异戊酯-然后该重氮盐与乙酸酐类似于方法C反应,制备该2-卤代吡啶II:
优选在一种无水体系中,例如在含氯化氢的冰醋酸中,在二噁烷,无水乙醇,四氢呋喃,乙腈或在丙酮中进行该方法。
反应温度通常是自(-30)至80℃。
一般而言,以约化学计算量使用重氮化反应的成分;然而,使用过量的这些成分之一可以也是有利的,例如,对其它成分的转化尽可能完全而言。优选使用过量的亚硝酸酯,基于IX的量,高达约二倍摩尔量。
使用该乙酸酐,基于该重氮盐,以约等摩尔量或过量是有利。一般而言,已发现,基于该重氮盐的量,大量过量的乙酸酐(高达约100倍摩尔量)尤其有利。
该2-卤代吡啶II(其中R1=C1-C6-烷基亚磺酰基)可以随后被氧化成为对应化合物II(其中R1=C1-C6-烷基磺酰基),如对化合物I(其中R1=C1-C6-烷基亚磺酰基)描述于方法E中。
除另行说明外,上述的全部方法是在大气压或在受讨论的反应混合物的自生压力下进行为有利。
通常是以一种常用方式进行该反应混合物的精制,例如以水稀释该反应混合物及随后借过滤,结晶或溶剂萃取分离该产物,或除去该溶剂,在水与一种适当有机溶剂的混合物中分配该残留物及精制该有机相以得该产物。
在制备方法中,可以获得该取代2-苯基吡啶作为异构物混合物;然而,如有需要,也可以使用常用方法诸如结晶法或层析法,包括经一种光学活性吸附剂层析,将其分离为大体上纯的异构体。纯光学活性异构体可以有利地自适当光学活性起始材料制备。
可以由与对应阳离子的一种碱,优选一种碱金属氢氧化物或氢化物,反应生成该化合物I的农业上适用的盐。
I的盐(其中该金属离子不是一种碱金属离子)可以常用方式由该对应碱金属盐的阳离子交换制备,相似地,可以借氨,鏻,锍或氧化锍氢氧化物获得铵,鏻,锍及氧化锍盐。
化合物I及其农业上可用的盐以异构体混合物形式和以纯异构体形式均适于用作除草剂。含化合物I的除草组合物在非作物区控制植物非常有效,尤其是以高量施用。它们在作物诸如小麦,稻,玉米,大豆及棉花中对抗阅叶杂草及禾本科杂草而对作物植株不造成任何重大损害。主要在低量使用时观察到此效应。
视用于每一情况中的施用方法,该化合物I,或含化合物I的除草组合物,可以另行用于多种其它作物供消除不受欢迎的植物。适当的作物的例子如下:洋葱,菠萝,花生,芦笋,甜菜,制糖甜菜,芜菁,饲料芜菁,欧洲油菜,茶,红花,培甘,柠檬,雪柑,阿拉伯咖啡(大叶咖啡,利比亚咖啡),黄瓜,绊根草,胡萝卜,油棕,草莓,大豆,陆地棉(亚洲棉,亚洲棉,Gossypium vitifolium),向日葵,巴西橡胶,大麦,啤酒花,甘薯,核桃,兵豆,亚麻,Lycopersicon lycopersicum,Malus spec.,木薯,紫花苜蓿,Musa spec.,烟草(黄花烟草),油橄榄,水稻,皇帝豆,四季豆,欧洲云杉,松属,豌豆,欧洲甜樱桃,桃,洋梨,红醋栗,蓖麻,甘蔗,黑麦,马铃薯,高梁,可可,红花三叶草,小麦,硬粒小麦,蚕豆,葡萄,玉米。
此外,该化合物I也可以用于作物(其由于育种而耐受除草剂的作用,包括基因工程方法)。此外,该取代2-苯基吡啶I也适合用于植物的干燥和/或落叶。
作为干燥剂,它们尤其适合作物株诸如马铃薯,油菜,向日葵及大豆的空中部分的干燥。这容许这些重要作物株的完全机械采收。
也具经济利益的是促进采收,这借树的枝叶的裂开或减少成为可能,两者集中于一段时期,在柑橘类,橄榄及其它品种及多种苹果类,核果及坚果。该相同的机制,即,促进该株的果子或叶与嫩枝间切断组织的形成,对有用的植物植株的快速可控制的落叶具由重要性,尤其是棉花。
此外,缩短个别棉株的成熟期结果造成采收后受改良的纤维品质。
该化合物I,或含该化合物I的组合物,可以以例如即可喷洒水溶液,粉末,悬浮液的形态使用,还有高度浓缩的水,油性或其它悬浮液或分散体,乳液,油分散体,膏,尘粉,供撒布的材料或颗粒,借喷洒,雾化,撒粉,撒布或倾倒施用。使用的形态视意图的目的而定;在任何情况,必须保护根据本发明的活性化合物的极微细分布。
适当的惰性辅助剂主要是:中至高沸点的矿油馏分,诸如煤油及柴油,此外,煤焦油及植物或动物来源的油,脂族,环状及芳族烃,例如石蜡油,四氢萘,烷基化萘及其衍生物,烷基化苯基及其衍生物,醇类诸如甲醇,乙醇,丙醇,丁醇及环己醇,酮类诸如环己酮,强极性溶剂类,例如胺类诸如N-甲基吡咯烷酮,及水。
含水使用形式可由乳剂浓缩物、悬浮剂、糊剂、湿粉剂或水可分散颗粒加水制备。为了制备乳剂、溶于油或溶剂的糊剂或油分散剂,基质可以湿剂、增粘剂、分散剂或乳化剂方式均化于水中。另外,可制备含活性成份、润湿剂、增粘剂、分散剂或乳化剂的浓缩物且视需要,溶剂或油可加水适当稀释。
适当的表面活性剂(配料)是芳族磺酸,例如,木素-,酚-,萘-及二丁基萘磺酸的及脂族酸的碱金属盐,碱土金属盐及铵盐,磺酸烷基酯及烷芳基酯,硫酸烷基酯,乙硫酸月桂酯及脂肪醇硫酸酯,及硫酸化的十六-,十七-及十八醇的盐,及还有脂肪醇乙二醇醚的盐,磺化萘及其衍生物与甲醛的缩合物,萘的缩合物,或萘磺酸与酚及甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化的异辛基-,辛基-,壬基酚,烷苯基或三丁苯基聚乙二醇醚,烷芳基聚醚醇,异十三醇,脂肪醇/环氧乙烷缩合物,乙氧基化的蓖麻子油,聚氧乙烯烷基醚或聚氧丙烯烷基醚,月桂醇聚乙二醇醚乙酸酯,山梨糖醇酯,木素亚硫酸法废液或甲基纤维素。
粉末,用供撒布的材料及尘粉可以借混合或研磨该活性化合物连同一种固体载体制备。
颗粒,例如涂覆的颗粉,浸渍的颗粒及均质颗粒,可以借结合该活性化合物至固体载体制备。固体载体是矿土,诸如硅氧化物,硅凝胶,硅酸盐,滑石,高岭土,石灰石,石灰,白垩,胶块土,黄土,粘土,白云石,硅藻土,硫酸钙,硫酸镁,氧化镁,研磨合成材料,肥料诸如硫酸铵,磷酸铵及硝酸铵,尿素,及植物来源的产物,诸如谷类粉,树皮粉,木材粉及坚果壳粉,纤维素粉末,或其它固体载体。
在即可使用的配方中该活性化合物I的浓度可以在宽广范围内变动。一般而言,该配方含0.001至98重量%,优选0.01至95重量%的至少一种活性化合物。以纯度为90%至100%,优选95%至100%(根据NMR光谱)使用该活性化合物。
以下的配方例例证此类产物的制备方法:
I.溶解20重量份的化合物No.Ia.363于一种由80重量份的烷
基化苯,10重量份的8至10摩尔的环氧乙烷对1摩尔的油酸N-单乙醇胺的加合物,5重量份的十二烷苯基磺酸钙及5重量份的40摩尔的环氧乙烷对1摩尔的蓖麻子油的加合物组成的混合物中。倒该溶液至100,000重量份的水中及细微地分布其于其中,以得一种水分散体其含0.02重量%的该活性化合物。
II.溶解20重量份的化合物No.Ia.362于一种由40重量份的环己酮,30重量份的异丁醇,20重量份的7摩尔的环氧乙烷对1摩尔的异辛基酚的加合物及10重量份的40摩尔的环氧乙烷对1摩尔的蓖麻子油的加合物组成的混合物中。倒该溶液至100,000重量份的水中及细微地分布其于其中,以得一种水分散体其含0.02重量%的该活性化合物。
III.溶解20重量份的活性化合物No.Ia.374于一种由25重量份的环己酮,65重量份的一种沸点210至280℃的磺油馏分及10重量份的40摩尔的环氧乙烷对1摩尔的蓖麻子油的加合物组成的混合物中。倒该溶液至100,000重量份的水中及细微地分布其于其中,以得一种水分散体其含0.02重量%的该活性化合物。
IV.将20重量份的活性化合物No.Ia.363与3重量份的二异丁基萘-α-磺酸钠,17重量份的一种自亚硫酸法废液的木质磺酸的钠盐及60重量份的粉碎硅凝胶彻底混合,及在一台锤磨机中研磨该混合物。细微分布该混合物于20,000重量份的水中,以得一种喷洒混合物其含0.1重量%的该活性化合物。
V.将3重量份的活性化合物No.Ia.362与97重量份的微细高岭土混合。此得一种尘粉其含3重量%的该活性化合物。
VI.将20重量份的活性化合物No.Ia.374与2重量份的十二烷苯基磺酸钙,8重量份的脂肪醇聚乙二醇醚,2重量份的一种酸/尿素/甲醛缩合物的钠盐及68重量份的一种石蜡性矿油密切混合。此得一种稳定的油性分散体。
VII.溶解1重量份的化合物No.Ia.363于一种由70重量份的环己酮,20重量份的乙氧基化的异辛基酚及10重量份的乙氧基化的蓖麻子油组成的混合物中。此得一种稳定的乳液浓缩物。
VIII.溶解1重量份的化合物No.Ia.374于一种由80重量份的
环己酮及20重量份的WettolEM 31(=基于乙氧基化的蓖麻子油的
非离子乳化剂;BASF AG)组成的混合物中。此得一种稳定的乳液
浓缩物。
可以在出苗前或出苗后施用该活性化合物I或该除草组合物。倘若某些作物株较不能容耐该活性化合物,可以使用施用技术在其中喷洒该除草组合物,以该喷洒器械的助,以如此方式使其尽可能少与该敏性作物株的叶接触,而该活性化合物达到生长于其下的不受欢迎的植物的叶,或该裸露的土地表面(针对后者,置放一旁)。
活性化合物I的施用量是自0.001至3.0,优选0.01至1.0公斤/公顷的有效物质(a.s.),视控制目标,季节,目标植物及生长阶段而定。
为加宽作用范围及达成协合效应,该取代2-苯基吡啶I可以与为数甚多的其它除草或生长-调节活性化合物组群的代表混合及然后附随地施用。用于这些混合物的适当成分是,例如,1,2,4-噻二唑,1,3,4-噻二唑,酰胺,氨基磷酸及其衍生物,氨基三唑,酰基苯胺,芳氧基/杂芳氧基烷羧酸及其衍生物,苯基甲酸及其衍生物,苯并噻二嗪酮,2-(杂芳酰基/芳酰基)-1,3-环己二酮,杂芳基芳基酮,苯基甲基异噁唑烷酮,间-CF3-苯基衍生物,氨基甲酸酯,喹啉羧酸及其衍生物,氯N-乙酰苯胺,环己烷-1,3-二酮衍生物,二嗪,二氯丙酸及其衍生物,二氢苯基并呋喃,二氢呋喃-3-酮,二硝基苯胺,二硝基酚,二苯基醚,联吡啶,卤素羧酸及其衍生物,尿素,3-苯基尿嘧啶,咪唑,咪唑啉酮,N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺,噁二唑,环氧乙烷,酚,芳氧基-及杂芳氧基苯基氧丙酸酯,苯基乙酸及其衍生物,2-苯基丙酸及其衍生物,吡唑,苯基吡唑,哒嗪,吡啶羧酸及其衍生物,嘧啶基醚,磺酰氨基,磺酰基-尿素,三嗪,三嗪酮,三唑啉酮,三唑羧酰胺及尿嘧啶。
施用该化合物I单独或附随地与其它除草剂组配,以与其它作物保护剂的一种混合物的形态,例如连用用于控制害虫或植物病原生性霉菌或细菌的药剂。尚有受关注者是与无机盐溶液溶混性,其是用于处理营养及痕量元素不足。也可以加入非植物毒性油及油浓缩物。
制备例
例1(表1中化合物Ia.363):
一滴一滴加入8.5毫升的氯化异丙基镁在四氢呋喃中的2摩尔溶液至3.7克的5-溴-2-氯-4-氟茴香醚在80毫升的四氢呋喃中的溶液。于搅拌30分钟后,所得的混合物,于0℃,是滴加至5.7克的3-氯-5-(甲磺酰氧基)-2-(苯基磺酰基)吡啶在100毫升的四氢呋喃中的溶液。然后于约20℃搅拌该全部反应混合物17小时。然后加热该混合物于回流温度为时72小时。然后馏出该低沸腾分。以1升的乙酸乙酯摄取该残留物,以2×250毫升水洗涤该有机相,经硫酸镁干燥及最后浓缩。借硅凝胶色谱法(移动相:乙酸乙酯/环己烷(1∶1))纯化该粗产物。产量:2.9克。
中间物1.1:3-氯-2-羟基-5-硝基吡啶
最初,溶解190.9克的2-羟基-5-硝基吡啶于650毫升在50℃的浓盐酸中。在1小时期间滴加42.9克的氯酸钾在600毫升的水中的溶液至此混合物中。于冷却至约20℃后,搅拌该混合物另45分钟及然后冷却至0℃。随后滤出固体部分及悬浮于200毫升的水中。最后滤出该不溶解的产物及于减压下在50℃干燥。产量:162.9克;熔点:197-198℃。
中间物1.2:2,3-二氯-5-硝基吡啶
于0℃,加入39.9克的喹啉及,5分钟后及每次小量,108克的3-氯-2-羟基-5-硝基吡啶至95克的三氯氧化磷中。于添加另30毫升的三氯氧化磷后,加热该混合物于回流温度为时2小时。为精制,冷却该反应混合物至50-60℃及搅拌至约3升的冰水中。随后搅拌该混合物为时另2小时,及然后滤出所得的固体部分,以500毫升的水洗涤及于减压下干燥。产量:110.7克。
中间物1.3:2,3-二氯-5-氨基吡啶
加入1克的铂/活性炭至67.4克的2,3-二氯-5-硝基吡啶在800毫升的四氢呋喃中的溶液。随后导入25升的氢,及接近该反应终结时加热该反应混合物至50℃。然后滤除该不溶解成分。浓缩该滤液。产量:56克。
中间物1.4:2,3-二氯-5-叠氮基吡啶四氟硼酸酯
于0℃,滴加45.6克的亚硝酸钠在100毫升的水中的溶液至98克的2,3-二氯-5-氨基吡啶在600毫升的浓度48%四氟硼酸中的溶液中。1小时后,滤出所得的固体及,为防止突然分解,在湿态下进一步处理。
中间物1.5:5-乙酰氧-2,3-二氯吡啶
加热42克的重氮盐(来自中间体1.4)及300毫升的乙酸酐于回流温度为时1小时。随后浓缩该混合物。以400毫升的二乙醚溶解该残留物及以2×200毫升的水洗涤该溶液,经硫酸镁干燥及最后再浓缩。借硅凝胶色谱法(移动相:乙酸乙酯/环己烷(1∶1))纯化该粗产物。产量:16克。
中间物1.6:2,3-二氯-5-羟基吡啶
于0℃,加入13克的氢氧化钠在80毫升的水中的溶液至16克的5-乙酰氧-2,3-二氯吡啶在100毫升的冰水中。随后开始时于0℃搅拌该混合物1小时及然后于约20℃搅拌17小时,及然后以150毫升的乙酸乙酯洗涤该反应混合物。借加入乙酸酸化该混合物至pH4-5,及然后以乙酸乙酯每次100毫升萃取三次。以硫酸镁干燥该并合有机相及最后浓缩。产量:12.2克。
中间物1.7:2,3-二氯-5-(甲磺酰氧基)吡啶
于0℃,最初加入7.9克的三乙氨基及然后8.5克的甲硫酰氯至11.6克的2,3-二氯-5-羟基吡啶在150毫升的二氯甲烷中。随后于约20℃搅拌该混合物为时17小时及然后以100毫升的水洗涤。该有机相经硫酸镁干燥及然后浓缩。所得的粗产物借硅凝胶色谱法(移动相:乙酸乙酯/环己烷(1∶1))纯化。产量:9.1克。
中间物1.8:2-氯-5-(甲磺酰氧)-2-(苯基磺酰基)吡啶
于170℃加热8.9克的2,3-二氯-5-(甲磺酰氧基)吡啶,4.2克的噻吩及20毫克的铜粉的混合物2小时,冷却至约20℃后,一滴一滴首先与50毫升的冰醋酸及20毫升的水的混合物混合及然后,在冷却下,与157克的次氯酸钠水溶液(含13%的活性氯)和50毫升的水的混合物混合。随后于约20℃搅拌该混合物17小时,及然后搅拌该全部反应混合物至300毫升的水中。以乙酸乙酯每次200毫升萃取该混合物3次,及然后以硫酸镁干燥该合并有机相及最后浓缩。该粗产物借硅凝胶色谱法(移动相:乙酸乙酯/环己烷(1∶1))纯化,产量:5.7克。
例2(表1中化合物Ia.363)
最初,滴加13.5克的碳酸氢钠在100毫升的水中的溶液至2,3-二氯-5-甲磺酰基吡啶,4-氯-2-氟-5-甲氧基硼酸及100毫升的四氢呋喃的混合物中,及然后加入1克的四(三苯基膦)钯。于回流温度搅拌该混合物为时14小时,此后加入150毫升的甲基叔丁基醚至该反应混合物。随后分离该有机相。以甲基叔丁基醚每次150毫升萃取该水相两次。然后以硫酸镁干燥该合并有机相及最后浓缩。该粗产物借硅凝胶色谱法(移动相:乙酸乙酯/环己烷(1∶1))纯化。产量:5.0克。
例3(表1中化合物Ia.362)
滴加14.4毫升的三溴化硼在二氯甲烷中的1M溶液至4.8克的2-(4-氯-2-氟-5-甲氧苯基)-3-氯-5-(甲磺酰氧基)吡啶(化合物No.Ia.363)在100毫升的二氯甲烷中。随后于约20℃搅拌该混合物37小时及然后于回流温度搅拌7小时。然后滴加100毫升的冰水至该反应混合物。将相分离及以二氯甲烷每次100毫升萃取该水相两次。最后以硫酸镁干燥该合并有机相及然后浓缩。该粗产物借硅凝胶色谱法(移动相:乙酸乙酯/环己烷(1∶1))纯化。产量:3.2克。
例4(表1中化合物Ia.374)
依次加入0.3克的碳酸钾及0.25克的烯丙基溴至0.6克的2-(4-氯-2-氟-5-羟基苯基)-3-氯-5-(甲磺酰氧基)吡啶(化合物No.Ia.362)在100毫升的二甲基甲酰胺中。随后于约20℃搅拌该反应混合物17小时及然后导入至300毫升的水中。所得的有价值产物以3×150毫升的甲基叔丁基醚萃取。以硫酸镁干燥该合并有机相及最后浓缩。该粗产物借硅凝胶色谱法(移动相:乙酸乙酯/环己烷(1∶1))纯化。产量:80毫克。
以上所述的活性化合物I以及以相似方式制备的根据本发明的其它化合物的物理数据列于以下表2中:
表2
No. | R5 | 熔点℃ |
Ia.159 | OCH2-CO-OCH3 | 油 |
Ia.169 | OCH(CH3)-CO-OCH3(外消旋物及R对映体) | 油 |
Ia.362 | OH | 132-133 |
Ia.363 | OCH3 | 118-120 |
Ia.374 | OCH2-CH=CH2 | 油 |
Ia.381 | OCH2-C≡CH | 110-112 |
Ia.636 | OCH(CH3)-CO-OCH2-CH2-OCH3(R对映体) | 油 |
Ia.637 | OCH(CH3)-CO-OCH2-CH=CH2(R对映体) | 油 |
使用例(除草活性)
由以下温室试验证明取代2-苯基吡啶I的除草活性:
使用塑料花盆作为培养容器,贮有约3%的腐植质的壤沙土作为基质。分别播种每种试验植物的种籽。
对出苗前处理,该活性化合物,其已悬浮或乳化于水中,是于播种后借微细分散的喷嘴直接施加。温和灌溉这些容器以促进发芽及生长,随后以透明塑料罩覆盖直至植物生根。此罩盖造成试验植物的均匀发芽,除非这受到该活性化合物的不利影响。
对出苗后处理,首先让试验植物生长至3至15公分的高度,视该植物习性而定,然后以该活性化合物处理,其已悬浮或乳化于水中。为此目的,试验植物直接播种及生长于该相同的容器中,或其首先分别生长为秧苗及在处理前数天移植至试验容器中。出苗后施用量是15.6及7.8克的有效物质/公顷。
视植物的品种,这些植物保持于10-25℃或20-35℃。试验期间是2至4周。在此期间,照顾这些植物,及评估其对个别处理的响应。
使用一种尺度自0至100进行评估。100意指该植物没有出苗或至少地面以上部分完全毁损,及0意指没有损害,或正常生长。
用于该温室试验的植物是以下品种:
学名 | 俗名 |
Abutilon theophrasti | velvetleaf苘麻 |
Amaranthus retroflexus | redroot pigweed反枝苋 |
Chenopodium album | lambsquarters(goosefoot)藜 |
Ipomoeaspecies | morning glory旋花科 |
Polygonum persicaria | redshan春蓼 |
以15.6及7.8克有效物质/公顷的施用量,化合物Nos.Ia.169,Ia.381及Ia.636(R对映体)对上述植物展示极良好除草效能。
使用例(干燥/落叶效能)
使用的试验植物是已在温室条件下生长(相对大气湿度50至70%;昼/夜温度27/20℃)的四片叶(没有子叶)的幼棉株。
以活性化合物的含水配方(基于喷洒混合物,添加0.15重量%的脂肪醇烷醇盐PlurafacLF700,低泡沫表面活性剂,来自BASF AG)对该幼棉株进行叶处理至滴流点。施用的水量是1000升/公顷(折算)。13天后,测定落叶的数目及落叶的程度(以%计)。
未处理的对照株没有落叶。
Claims (14)
1.一种式I的取代2-苯基吡啶,其中:n是0或1;R1是氨基磺酰基,C1-C6-烷基亚磺酰基,C1-C6-烷基磺酰基或C1-C6-卤代烷基磺酰基;R2,R3彼此独立地是氢或卤素;R4是氰基,羟基,卤素,C1-C6-烷氧基或苯基甲氧基,其中该苯基环可以是未取代的或可以携带自1至3个取代基,在每个情况取代基选自羟基,卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-卤代烷氧基,羟基羰基,(C1-C6-烷氧基)羰基和(C1-C6-烷氧基)羰基-C1-C6-烷氧基;R5是氢,硝基,氰基,羟基氨基,卤素,C1-C6-烷基,C1-C6-卤代烷基,-COCl,-CO-OR6,-CO-N(R7)R8,-CO-O-(C1-C4-亚烷基)-CO-OR6,-CO-O-(C1-C4-亚烷基)-CO-N(R7)R8,-X1-(C1-C4-亚烷基)-CO-R6,-X1-(C1-C4-亚烷基)-CO-OR6,-X1-(C1-C4-亚烷基)-CO-O-(C1-C4-亚烷基)-CO-OR6,-X1-(C1-C4-亚烷基)-CO-N(R7)8,-X1-R9,-CH=C(R10)-CO-OR6,-CH=C(R10)-CO-O-(C1-C4-亚烷基)-CO-OR6,-CH=C(R10)-CO-N(R7)R8,甲酰基,-CO-R6,-C(R8)=N-OR15,-X1-(C1-C4-亚烷基)-C(R8)=N-OR15,-CH=C(R10)-C(R8)=N-OR15,-CH(C1-C6-烷氧基)2,-N(R16)R17,-N(R16)-SO2-(C1-C6-烷基),-N(R16)-CO-(C1-C6-烷基),氯磺酰基,羟基磺酰基或-SO2-N(R18)R19;R6是氢,C1-C6-烷基,C1-C6-卤代烷基,C3-C6-链烯基,C3-C6-炔基,C3-C6-环烷基或C1-C6-烷氧基-C1-C6-烷基;R7是氢或C1-C6-烷基;R8是氢,羟基,C1-C6-烷基,羟基羰基-C1-C6-烷基,(C1-C6-烷氧基)羰基-C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷氧基,苯基-C1-C6-烷氧基,C3-C6-链烯氧基或C3-C6-炔氧基;R9是氢,C1-C6-烷基,C1-C6-卤代烷基,C3-C6-链烯基,C3-C6-炔基,C3-C6-环烷基或C1-C6-烷氧基-C1-C6-烷基;R10是氢,卤素或C1-C6-烷基;R11-R14彼此独立地是氢,C1-C6-烷基或(C1-C6-烷氧基)羰基;R15是氢,C1-C6-烷基,苯基-C1-C6-烷基,(C1-C6-烷氧基)羰基-C1-C6-烷基,C3-C6-链烯基或C3-C6-炔基;R16是氢或C1-C6-烷基;R17是氢,C1-C6-烷基,羟基羰基-C1-C6-烷基,(C1-C6-烷氧基)羰基-C1-C6-烷基或C1-C6-烷氧基;R18是氢或C1-C6-烷基;R19是氢,C1-C6-烷基,羟基羰基-C1-C6-烷基,(C1-C6-烷氧基)羰基-C1-C6-烷基或C1-C6-烷氧基;X1-X3彼此独立地是氧或硫;以及其中R6=氢的化合物I的农业上可用的盐。
2.根据权利要求1的式I的取代2-苯基吡啶及其盐,其中R5是氢,硝基,氰基,羟基氨基,C1-C6-烷基,C1-C6-卤代烷基,-COCl,-CO-OR6,-CO-O-(C1-C4-亚烷基)-CO-OR6,-O-(C1-C4-亚烷基)-CO-OR6,-O-(C1-C4-亚烷基)-CO-O-(C1-C4-亚烷基)-CO-OR6,-OR9,甲酰基,-CH=N-OR15或-NH2;R6是氢,C1-C6-烷基,C3-C6-链烯基,C3-C6-炔基或C1-C6-烷氧基-C1-C6-烷基;R9是氢,C1-C6-烷基,C3-C6-链烯基或C3-C6-炔基及R15是C1-C6-烷基。
3.根据权利要求1的式I的取代2-苯基吡啶及式I的农业上可用的盐,用作除草剂或用于植物的干燥作用和/或落叶作用。
4.一种除草组合物, 包含除草有效量的至少一种根据权利要求1的取代2-苯基吡啶或一种式I的农业上可用的盐及至少一种惰性液体和/或固体载体及还有,若需要,至少一种表面活性剂。
5.一种用于植物的干燥作用和/或落叶作用的组合物,包含至少一种根据权利要求1的式I的取代2-苯基吡啶或式I的一种农业上可用的盐,其量使其作为一种干燥剂和/或落叶剂,及至少一种惰性液体和/或固体载体及,若需要,至少一种表面活性剂。
6.一种制备除草有效组合物的方法,包括混合除草有效量的至少一种根据权利要求1的式I的取代2-苯基吡啶或式I的一种农业上可用的盐,及至少一种惰性液体和/或固体载体及,若需要,至少一种表面活性剂。
7.一种制备作为干燥剂和/或落叶剂的组合物的方法,包括混合至少一种根据权利要求1的式I的取代2-苯基吡啶或式I的一种农业上可用的盐,其量使其作为一种干燥剂和/或落叶剂,及至少一种惰性液体和/或固体载体及,若需要,至少一种表面活性剂。
8.一种控制不受欢迎的植物的方法, 包括使除草有效量的至少一种根据权利要求1的式I的取代2-苯基吡啶或式I的一种农业上可用的盐作用于植物,其生长场所或种子上。
9.一种用于植物的干燥作用和/或落叶作用的方法,包括使至少一种根据权利要求1项的式I的取代2-苯基吡啶或式I的一种农业上可用的盐作用于植物株上,其量使其具有干燥和/或落叶作用。
10.根据权利要求9的方法,其中棉花被处理。
11.一种制备根据权利要求1的其中n是1以及R1和R5不含任何可氧化硫的式I取代2-苯基吡啶的方法,其包括在一种惰性溶剂/稀释剂中氧化其中n是0的适当取代的2-苯基吡啶。
13.根据权利要求12的方法,其中II与其中M1是B(OH)2,Mg-Cl,Mg-Br,Mg-I,Zn-Cl,Zn-Br或Zn-I的式III有机金属化合物反应。
14.一种式IIa的2-卤代吡啶其中Hal是氯或溴及R1如权利要求1中所定义。
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CN102464611A (zh) * | 2010-11-03 | 2012-05-23 | 中国中化股份有限公司 | 一种取代的联芳香基苯磺酰胺类化合物与用途 |
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EP1140847B1 (de) | 2002-12-18 |
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