CN1135211A - 苯基磺酰脲，其制备方法及其用作除草剂和植物生长调节剂 - Google Patents
苯基磺酰脲，其制备方法及其用作除草剂和植物生长调节剂 Download PDFInfo
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- CN1135211A CN1135211A CN94194137A CN94194137A CN1135211A CN 1135211 A CN1135211 A CN 1135211A CN 94194137 A CN94194137 A CN 94194137A CN 94194137 A CN94194137 A CN 94194137A CN 1135211 A CN1135211 A CN 1135211A
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000004009 herbicide Substances 0.000 title claims abstract description 10
- -1 Phenylsulfonyl ureas Chemical class 0.000 title claims description 30
- 230000002363 herbicidal effect Effects 0.000 title claims description 10
- 239000005648 plant growth regulator Substances 0.000 title claims description 4
- 235000013877 carbamide Nutrition 0.000 title description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 9
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2849
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 57
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000006467 substitution reaction Methods 0.000 claims description 24
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 9
- 230000008635 plant growth Effects 0.000 claims description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 238000009333 weeding Methods 0.000 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 claims description 3
- 230000001473 noxious effect Effects 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003630 growth substance Substances 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 150000001345 alkine derivatives Chemical class 0.000 claims 2
- 125000003700 epoxy group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 229920001228 polyisocyanate Polymers 0.000 claims 1
- 239000005056 polyisocyanate Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000004306 triazinyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1196
- 239000000460 chlorine Substances 0.000 description 74
- 241000196324 Embryophyta Species 0.000 description 37
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000011149 active material Substances 0.000 description 23
- 150000002148 esters Chemical class 0.000 description 22
- 159000000000 sodium salts Chemical class 0.000 description 22
- 244000025254 Cannabis sativa Species 0.000 description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000008187 granular material Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 239000004563 wettable powder Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
- PHVNLLCAQHGNKU-UHFFFAOYSA-N Dimethipin Chemical compound CC1=C(C)S(=O)(=O)CCS1(=O)=O PHVNLLCAQHGNKU-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 241001597008 Nomeidae Species 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 244000082988 Secale cereale Species 0.000 description 4
- 235000007238 Secale cereale Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 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 4
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 4
- QZSGYPOMAGZIOZ-UHFFFAOYSA-M sodium;(2,2-dimethyl-1h-quinolin-4-yl)methanesulfonate Chemical compound [Na+].C1=CC=C2C(CS([O-])(=O)=O)=CC(C)(C)NC2=C1 QZSGYPOMAGZIOZ-UHFFFAOYSA-M 0.000 description 4
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- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 4
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- DGDAVTPQCQXLGU-UHFFFAOYSA-N 5437-38-7 Chemical class CC1=CC=CC(C(O)=O)=C1[N+]([O-])=O DGDAVTPQCQXLGU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
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- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 239000003337 fertilizer Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical class O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 3
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
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- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
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- MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 description 2
- AOQMRUTZEYVDIL-UHFFFAOYSA-N Flupoxam Chemical compound C=1C=C(Cl)C(COCC(F)(F)C(F)(F)F)=CC=1N1N=C(C(=O)N)N=C1C1=CC=CC=C1 AOQMRUTZEYVDIL-UHFFFAOYSA-N 0.000 description 2
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- 235000010469 Glycine max Nutrition 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 2
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- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical compound C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 1
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- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
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- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
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- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
权利要求1中定义的式(I)化合物及其盐适合作为选择性除草剂，见式(1)，
其中R1为CO-Q-R8，其中R8＝H或R，R2和R3为H或(C1-C4)烷基，R4为H，R，RO，OH，RCO，RSO2，PhSO2，R5为RSO2，PhSO2，PhCO，RNHSO2，R2NSO2，RCO，CHO，COCOR′，CW-T-R9，CW-NR10R11，CW-N(R12)2，或R4和R5一起为(CH2)mB或-B1-(CH2)m1B-链，其中B＝SO2，CO；m＝3，4；m1＝2，3，；T和W＝O，S；Q＝O，S，NR13,其中R13＝H,R;R6＝H，R，RO，RCO，ROCO，Hal，NO2，CN；R7＝H,CH3;R9＝R;R10,R11＝H,R;N(R12)2＝杂环，Ａ＝嘧啶基和三嗪基或其类似的基团。可通过相似方法从式Ⅱ磺酰胺制备上述化合物，一些式(Ⅱ)化合物是新的(见权利要求４)。
Description
已知一些苯基磺酰脲具有除草和调节植物生长的性质；参见US-A-4,786,314，US-A-4,927,453和WO89/10921。可是在一些情况下上述苯基磺酰脲在应用上存在一些缺点，例如残效高或对重要的作物选择性差。
现已发现在苯环上具有一定基团的苯基磺酰脲可有效地用作除草剂或植物生长调节剂。本发明涉及式(I)的化合物或其盐，
其中R1为CO-Q-R8，R2和R3各自独立的为H或(C1-C4)烷基，R4为H，未取代或被一或多个下组包括的基团取代的(C1-C8)烷基，上述取代基团由卤素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)烷基磺酰基、[(C1-C4)烷氧基]羰基和CN组成，或为未被取代或被一至多个卤原子取代的(C3-C6)链烯基，或为未被取代或被一至多个卤原子取代的(C3-C6)链炔基，或为羟基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或(C1-C4)烷基磺酰基，后三个基团各自未被取代或在烷基部分被一至多个卤原子或被(C1-C4)烷氧基或(C1-C4)烷硫基取代，或为苯基磺酰基，其中苯基是未被取代或优选被一至多个下述基团取代，取代基由卤素、CN、NO2、(C1-C4)烷基、(C1-C4)卤代烷基和(C1-C4)烷氧基组成，和R5为(C1-C4)烷基磺酰基或(C3-C6)链烯基磺酰基，后两个基团各自未被取代或被一至多个卤原子或被(C1-C4)烷氧基或(C1-C4)烷硫基取代的，或为苯基磺酰基或苯基羰基，后两个基团的苯基各自未被取代或优选被一或多个下述基团取代，上述取代基由卤素、CN、NO2、(C1-C4)烷基、(C1-C4)卤代烷基和(C1-C4)烷氧基组成，或为单-或二-[(C1-C4)烷基]氨基磺酰基或[(C1-C6)烷基]羰基，后三个基团各自未被取代或被一或多个下述基团取代，上述取代基由卤素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)烷基磺酰基、[(C1-C4)烷基]羰基、[(C1-C4)烷氧基]羰基和CN组成，或为甲酰基，式-CO-CO-R’的基团其中R’＝H，OH，(C1-C4)烷氧基或(C1-C4)烷基，或为[(C3-C6)环烷基]羰基，[(C2-C6)链烯基]羰基或[(C2-C6)链炔基]羰基，后三个基团各自未被取代或被一或多个卤原子取代，或为下式的基团
或R4和R5一起为式(-CH2)mB-或-B1-(CH2)ml-B-的链，上述链是未被取代或被一个或多个，优选直至四个(C1-C3)烷基取代和m为3或4或m1为2或3，和W为氧或硫原子(即O或S)，B和B1各自独立为SO2或CO，Q为O，S或-NR13-，T为O或S，R6为H，(C1-C4)烷基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或[(C1-C4)烷氧基]羰基，后四个基团各自未被取代或在烷基部分被一至多个卤原子取代，或为卤素，NO2或CN，R7为H或CH3，R8为H，(C1-C4)烷基，(C3-C4)链烯基或(C3-C4)链炔基，后三个基团各自未被取代或被一或多个由卤素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基组成的一组基团取代，R9为(C1-C4)烷基，(C3-C4)链烯基或(C3-C4)链炔基，后三个基团各自未被取代或被一或多个由卤素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基组成的一组基团取代，R10和R11各自独立地为H，(C1-C4)烷基，(C3-C4)链烯基或(C3-C4)链炔基，后三个基团各自未被取代或被一或多个由卤素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1-C4)烷氧基]羰基组成的一组基团取代，R12基团与氮原子一起为5或6元杂环，上述杂环在可能的氧化态中可含有一个其它N，O和S杂原子，且是未被取代或被(C1-C4)烷基或氧基取代，或被苯环稠和，R13为H，(C1-C4)烷基，(C3-C4)链烯基或(C3-C4)链炔基，后三个基团各自未被取代或被一或多个由卤素、(C1-C4)烷氧基、(C1-C4)烷硫基组成的一组基团取代，A为下式的基团
X和Y基团之一是氢，卤素，(C1-C3)烷基或(C1-C3)烷氧基，后两个基团是未被取代或被卤素单取代或多取代或被(C1-C3)烷氧基单取代，和X和Y基团的另一个是氢，(C1-C3)烷基，(C1-C3)烷氧基或(C1-C3)烷硫基，后三个含有烷基的基团是未被取代或被卤原子单或多取代或被(C1-C3)烷氧基或(C1-C3)烷硫基单取代或二取代，或为式NR14R15的基团，(C3-C6)环烷基，(C2-C4)链烯基，(C2-C4)链炔基，(C3-C4)链烯氧基，(C3-C4)链炔氧基，Z为CH或N，R14和R15各自彼此独立地为H，(C1-C3)烷基，(C3-C4)链烯基，X1为CH3、OCH3、OC2H5或OCHF2，Y1为-O-或-CH2-X2为CH3、C2H5或CH2CF3Y2为OCH3、OC2H5、SCH3、SCH2CH3、CH3或C2H5，X3为CH3或OCH3，Y3为H或CH3，X4为CH3、OCH3、OC2H5、CH2OCH3或Cl，Y4为CH3、OCH3、OC2H5或Cl和Y5为CH3、C2H5、OCH3或Cl。在式(I)和下文中，烷基、烷氧基、卤代烷基、烷基氨基和烷硫基以及相应的不饱和和/或取代的基团在碳架中各自可为直链和支链的基团。单独的烷基或作为如烷氧基、卤代烷基等的组成的烷基是甲基、乙基、正或异丙基、正-、异-、叔-或2-丁基；链烯基或链炔基具有相应于烷基可能的不饱和基团的定义，如2-丙烯基、2-或3-丁烯基、2-丙炔基、2-或3-丁炔基。卤素为氟、氯、溴或碘；卤代烷基是被一或多个卤原子取代的烷基；卤代烷基的实例为CF3、CHF2和CH2CF3。取代苯基优选为被一或多个，优选1，2或3个下组基团取代的苯基，上组取代基团由卤素，如F、Cl、Br和I，优选F、Cl和Br，以及烷基、卤代烷基、烷氧基、卤代烷氧基、羟基、氨基、硝基、氰基、烷氧羰基、烷基羰基、甲酰基、氨基甲酰基、单-和二烷基氨基羰基、单-和二烷基氨基、烷基亚磺酰基和烷基磺酰基组成，且对于含有碳原子的基团，上述含有一至四个碳原子、特别1或2碳原子的基团是优选的。在此一般优选的取代基为由卤素，例如氟和氯、C1-C4-烷基、优选甲基或乙基，C1-C4-卤代烷基、优选三氟甲基，C1-C4-烷氧基、优选甲氧基或乙氧基，C1-C4-卤代烷氧基，硝基和氰基组成的一组基团。
在需要时可被苯稠和和含有氮原子(例如，在N(R12)2的情况下)的5-或6-元杂环可以是饱和，不饱和或杂芳基，例如借助氮原子连接并选自下组的基团，上述基团由吡咯烷基、哌啶基、吡唑基、吗啉基、吲哚基、喹啉基、嘧啶基、三唑基、噁唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、噻唑基、噁唑基、吡咯基、咪唑基和苯并恶唑基。
本发明还涉及式(I)化合物的各种异构体，及其混合物。如在式(I)未具体指明的含有一或多个不对称碳原子或双键的式(I)化合物。式(I)包括通过具体空间构型确定的所有可能的立体异构体，如对映体、非对映体、E和Z异构体，上述所有的异构体都可通过常规方法从立体异构体的混合物或通过立体选择性反应结合应用立体化学纯的起始物而制备。
式(I)化合物可形成盐，其中-SO2-NH-基的氢原子被适于农用的阳离子置换。例如上述盐是金属盐、特别是碱金属盐或碱土金属盐、特别是钠和钾盐、或铵盐或与有机胺形成的盐。
特别令人感兴趣的是根据本发明的式(I)化合物或其盐其中R4为H，未取代或被一或多个下组包括的基团取代的(C1-C4)烷基，上述取代基团由卤素、(C1-C4)烷氧基、(C1-C4)烷硫基、(C1-C4)烷基磺酰基、[(C1-C4)烷氧基]羰基和CN组成，或为(C3-C4)链烯基、(C3-C4)链炔基、羟基，(C1-C4)烷氧基，[(C1-C4)烷基]羰基或(C1-C4)烷基磺酰基，后五个基团各自未被取代或在烷基部分被一至多个卤原子取代，或为苯基磺酰基，其中苯基是未被取代或被一或多个下述基团取代的，取代基由卤素、(C1-C4)烷基和(C1-C4)烷氧基组成，和R5为(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、苯基磺酰基或苯基羰基，后两个基团中的苯基各自未被取代或被一至多个选自卤原子、(C1-C4)烷基和(C1-C4)烷氧基的基团取代，或为单-或二-[(C1-C4)烷基]氨基磺酰基，未被取代或被一或多个卤原子或(C1-C4)烷氧基或(C1-C4)烷硫基取代的[(C1-C6)烷基]羰基，或为甲酰基、OHC-CO-、2-氧-(C3-C5)链烷酰基、[(C1-C4)烷氧基]草酰基、[(C3-C6)环烷基]羰基，[(C2-C4)链烯基]羰基或[(C2-C4)链炔基]羰基、或为下式的基团W为O或SR6为H、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基或卤素，R8各自为未被取代或被一或多个卤原子取代的(C1-C4)烷基，或为(C3-C4)链烯基或(C3-C4)链炔基，R9为H、未被取代或被一或多个卤原子或被(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷氧基]羰基和[(C1-C4)烷基]羰基取代的(C1-C4)烷基，R10和R11各自独立地为H、未被取代或被一或多个卤原子取代的(C1-C4)烷基、或为(C3-C4)链烯基或(C3-C4)链炔基、其中R10和R11至少一个不是氢，R12基团与氮原子一起为5或6元杂环，上述杂环在不同的氧化态中可含有一个其它N，O和S杂原子，且是未被取代或被(C1-C4)烷基或氧基取代，R13为H，未被取代或被一或多个由卤素原子取代的(C1-C4)烷基、或为(C3-C4)链烯基或(C3-C4)链炔基。
优选的式(I)化合物及其盐是其中W为氧原子和A为下式的基团的式(I)化合物
其中X、Y和Z如上述定义。特别优选的式(I)化合物或其盐，其中R4为H、(C1-C4)烷基、羟基或(C1-C4)烷氧基，R5为(C1-C4)烷基磺酰基、CHO、未被取代或被一或多个卤原子取代的[(C1-C4)烷基]羰基、或为[(C1-C4)烷氧基]草酰基、[(C3-C6)环烷基]羰基或下式的基团
其中W，T和R9至R12如上面式(I)中的定义，R6为H、(C1-C3)烷基、(C1-C3)烷氧基或卤素，A为下式的基团
Z为CH或N，优选为CH，和X和Y基团之一为卤素、(C1-C2)烷基、(C1-C2)烷氧基、OCF2H、CF3或OCH2CF3和X和Y的另一个为(C1-C2)烷基、(C1-C2)烷氧基或(C1-C2)卤代烷氧基。
鉴于便于制备或具有较好的生物活性的原因，其中基团-CR2R3-NR4R5相对于R1基团为邻位或对位或相对于磺基为邻位的根据本发明的式(II)化合物及其盐是特别令人感兴趣的；-CR2R3-NR4R5基优选的位置是R1基的对位。
本发明还涉及制备式(I)化合物及其盐的方法，其中包括a)式(II)的化合物与式(III)杂环氨基甲酸酯反应
R*-O-CO-NR7-A (III)其中R*是必要时被取代的苯基或(C1-C4)烷基，或b)式(IV)的苯基磺酰基氨基甲酸酯与式(V)的氨基杂环反应H-NR7-A (V)或c)式(VI)的磺酰基异氰酸酯与式(V)H-NR7-A的氨基杂或d)在一个单釜反应(Eintopfreaktion)中，首先在碱存在下使式(V)H-NR7-A的氨基杂环化物与光气反应，然后反应的中间体与式(II)的苯基磺酰胺反应，或e)在碱存在下式(VII)的磺酰氯与其中M＝NH4、Na或K的氰酸酯M-OCN以及式(V)H-NR7-A的氨基杂环化物反
f)在碱存在下上述式(II)的磺酰胺与式(V’)的(硫代)异氰酸酯反应
W＝C＝N-A (V’)，在式(II)-(VII)和(V’)中的基团R1-R7、A或W如在式(I)中的定义，在方法a)-e)中，最初获得的是W＝O的式(I)化合物。
式(II)化合物和式(III)化合物的反应优选在碱催化下，在惰性有机溶剂，例如二氯甲烷、乙腈、二噁烷或THF存在下，在0℃和溶剂沸点之间进行。使用的碱的实例为有机胺碱，如特别是R*＝(取代)苯基(参见EP-A-44 807)时，碱为1，8-二氮杂二环[5.4.0]十一-7-烯(DBU)，或特别是R*＝烷基(参见EP-A-166 516)时，碱为三甲基铵或三乙基铵。式(II)的磺酰胺是新化合物。其和其制备方法也是本发明的主题。以其中R2＝R3＝H和Q＝O的式(II)化合物为例，对其可能的制备方法在下面进行了详细的描述，且只要作一点改动就可将上述方法用于其中R2和R3不是氢和/或Q不是O的化合物的制备。
采用文献中已知的相似方法，以取代和未取代的甲基氨基苯磺酸(VIII)作为起始物(参见德国专利48 583,242页)时，最初通过重氮化作用和按Sandmeyer反应用KCN/CuCN将其转化成腈(IX)，将腈皂化，通过羧基的酯化作用和将磺基转化成叔丁基-保护的磺酰胺基后得到作为中间体的磺酰胺(X)(见图1)。
图1此外，以取代或未取代的甲基硝基苯甲酸(XI)作为起始物，通过酯化作用、硝基的还原、重氮化作用和与SO2/CuCl偶联(见H.Meerwein等人，Chem.Ber.90，841-1178(1957))和用叔丁基胺氨解可获得式(X)的磺酰胺(见图2)。
图2
同样磺酰胺(X)的制备可以取代或未取代的甲基硝基苯胺(XII)作为起始物。通过重氮化作用和与KCN/CuCN偶联得到相应的腈，其可通过氰基的水解并酯化成硝基苯甲酸酯(XIII)。然后可将图2中所述的硝基转化成叔丁基氨基磺酰基(见图3)。
图3
为了制备式(II)的磺酰胺，可在式(X)化合物的侧链进行卤化作用得到(XIV)，然后用胺或叠氮化物取代(XIV)上的卤原子，接着还原得到苄基胺(XV’)，再对氨基官能化并通过已知的相似方法(例如用CF3COOH)除去叔丁基保护基得到磺酰胺(II’)(见图4)。
图4 
类似地，该方法步骤还可用于制备其它式(II)化合物，其中在最后一步中使用式(XV)化合物
式(III)氨基甲酸酯可通过描述在南非专利申请82/5671和82/5045或EP-A-70 804(US-A-4,480101)或RD275056中的方法制备。
式(IV)化合物与氨基杂环(V)的反应优选在如二噁烷、乙腈或四氢呋喃的惰性的、质子惰性溶剂中，在0℃至溶剂的沸点之间的温度下进行。所需的起始物(V)是文献中已知的或可通过文献中已知的方法制备的。式(IV)的苯基磺酰基氨基甲酸酯可通过类似于US-A-4,684,393或US-A-4,743,290的方法获得。
式(VI)的苯基磺酰基异氰酸酯可通过类似于US-A-4,481,029的方法制备并可与氨基杂环(V)反应。
根据方法d)的式(V)化合物的光气化作用优选在如空间位阻的有机胺碱，例如三乙胺的存在下进行。根据方法d)与式(II)化合物随后进行的反应可通过类似于已知的方法进行(参见：EP-A-232067)。
式(VII)的磺酰氯可通过常规方法从相应的磺酸获得，例如，在如乙腈和/或环丁砜的惰性溶剂中或不在溶剂中通过加热至回流使钾盐与磷酰氯或亚硫酰氯反应得到(参见：Houben-Weyl-Klamann，“Methoden der organischen Chemie”，[有机化学方法]，第四版，E XI/2卷，1067-1073页，ThiemeVerlag，Stuttgart，1985)。
通过类似于化合物(XI)的反应，相应的磺酸可从适当的硝基化合物获得。
可选择地，在个别的情况下，磺酰氯(VII)可通过适当取代的苯甲酸酯的磺化作用(+氯化作用)或氯磺化作用制备；氯磺化作用是采用Houben-Weyl-Klamann，“Methoden der organischenChemie”，[有机化学方法]，第四版，E XI/2卷，1067页，ThiemeVerlag，Stuttgart，1985)；Houben-Weyl-Muller，“Methoden derorganischen Chemie”，[有机化学方法]，第四版，XI卷，563页，Thieme Verlag，Stuttgart，1955)的类似方法；磺化作用是采用Houben-Weyl-Klamann，“Methoden der organischenChemie”，[有机化学方法]，第四版，E XI/2卷，1055页，ThiemeVerlag，Stuttgart，1985)；Houben-Weyl-Muller，“Methoden derorganischen Chemie”，[有机化学方法]，第四版，IX卷，435页，Thieme Verlag，Stuttgart，1955)的类似方法。
采用文献中的已知方法(EP-A-232067，EP-A-166516)可获得式(V’)的(硫代)异氰酸酯。(硫代)异氰酸酯(V’)与化合物(II)的反应在-10℃至100℃，优选20至200℃下，在诸如丙酮或乙腈的惰性的质子惰性溶剂中，在适合的碱，例如N(C2H5)3或K2CO3的存在下进行。
优选于诸如水、甲醇或丙酮的惰性极性溶剂中，在0-100℃下制备式(I)化合物的盐。根据本发明，适合制备盐的碱的实例为碱金属碳酸盐，如碳酸钾，碱金属氢氧化物和碱土金属氢氧化物，例如NaOH或KOH，或氨或乙醇胺。
在上述方法中所指的“惰性溶剂”为各种在各自的反应条件下惰性的溶剂，但其不需要在所有的反应条件下呈惰性。
根据本发明的式(I)化合物对多种经济上重要的单子叶和双子叶有害植物具有极好的除草活性。本活性物质还对从根茎、砧木根或其它多年生器官萌生的而且难于防治的多年生杂草具有有效的作用。在本文中，无论活性物质在播种前、苗前或苗后使用都可以。
下面具体但非限定性地述及了根据本发明化合物可以防治的一些代表性的单子叶和双子叶杂草的谱系。
活性物质对其能有效发挥作用的杂草的实例为：单子叶杂草：一年生中的燕麦、黑麦草、看麦娘、虉草、稗、马唐、狗尾草以及莎草属和多年生冰草、狗牙根、白茅和蜀黍属，以及多年生莎草属。
对双子叶杂草能发挥作用的是，例如一年生的：猪殃殃、堇菜、婆婆纳、野芝麻、繁缕、苋、白芥、牵牛、母菊、麻和黄花稔属，和多年生的旋花、蓟、酸模和蒿属。
根据本发明的活性物质防治水稻生长条件下的杂草非常有效，上述杂草如：慈菇、泽泻、荸荠、藨草和莎草属。
如果在萌发前将根据本发明化合物施用到土壤表面，则或是能完全防止杂草幼苗萌发，或是杂草生长到子叶阶段后生长停止且最终在三至四周后，杂草全部死亡。
如果将活性物质在苗后施用到植物的绿色部分，在处理后短期内植物生长马上停止且杂草植物停留在施药时的生长期，或一段时间后完全死亡，因此以这种方式将对作物有害的杂草竞争及早、持继地加以消除。
尽管对单子叶和双子叶杂草具有极好所除草活性，根据本发明的化合物完全不损害经济作物或其损害很小，经济作物如小麦、大麦、黑麦、水稻、玉米、甜菜、棉花和大豆。根据上述原因，本发明的化合物非常适合在农作物中选择性地防治有害植物生长。
另外，根据本发明的物质对作物存在明显的调节植物生长的性质。它们介入代谢的调节并因此可用来有针对性地影响植物中含有的物质，和方便收获，例如通过最初的干燥和生长紧密。而且，它们可在不杀死植物的情况下，系统的防治和抑制不需要的植物生长。在许多单子叶和双子叶作物中，抑制植物生长具有很大作用，这是因为这样能减少或完全防止倒伏。
根据本发明的化合物可用于常规的制剂形式，如可湿性粉剂、可乳化浓缩物、可喷雾溶液、粉剂或颗粒剂。因此本发明还涉及含有式(I)化合物的除草和植物生长调节组合物。
根据预定的生物和/或物理化学参数，可以多种方式配制式(I)化合物。因此可能的制剂为：可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩物、可乳化浓缩液(EC)、乳液(EW)如水包油型和油包水型乳液、可喷雾溶液、浓悬浮液(SC)、油基或水基分散液、油混溶液剂、胶囊悬浮液(CS)、粉剂(DP)、种子包衣剂、散播和土壤施用颗粒剂、微胶囊形式的颗粒剂(GR)、喷洒颗粒剂、包覆颗粒剂和吸收颗粒剂、水分散颗粒剂(WG)、水溶颗粒剂(SG)、ULV制剂、微胶囊和蜡剂。
上述单独的制剂类型原则上是已知的且描述在：Winnacker-Kuchler，“Chemische Technologie”[化学技术]，7卷C.HauserVerlag Munich，第4版，1986；Wade van Valkenburg，“Pesticide Formulation”，Marcel Dekker N.Y.1973；K.Martens，“Spary Drying”手册，第3版，1979，G.Goodwin Ltd.London。
制剂中所需要的助剂如惰性材料、表面活性剂、溶剂和其它添加剂也是已知的并描述在：例如(Watkins，“Handbook ofInsecticide Dust Diluents and Carriers”，第二版，Darland Books，Caldwell N.J.，H.v.Olphen，“Introduction to Clay ColloidChemistry”，第二版，J.Wiley & Sons，N.Y.；C.Marsden，“Solvents Guide”，第二版，Interscience，N.Y.1963；McCutcheon’s“Detergents and Emulsifiers Annual”，MC Publ.Corp.，Ridgewood N.J.；Sisley and Wood，“Encyclopedia of SurfaceActive Agents”，Chem.Publ.Co.Inc.，N.Y.1964；Schonfeldt，“Grenzflchenaktive thylenoxidaddukte”[表面活性的环氧乙烷加成物]，Wiss.Verlagsgesell.，Stuttgart 1976；Winnacker-Küchler，“Chemische Technologie”[化学技术]，Volume 7，C.Hauser VerlagMunich，第4版，1986。
与其它已知农药活性成分如杀虫剂、杀螨剂、除草剂、杀菌基的组合物，以及与安全剂、肥料和/或生长调节剂的组合物也可以上述制剂为基础制备，例如以现用制剂或桶混合物的形式。
可湿性粉剂是能均匀分散于水中的制剂，且除了活性物质外，其中还含有一些离子和/或非离子型表面活性剂(湿润剂，分散剂)，例如聚乙氧基化烷基酚、聚乙氧基化脂肪醇、聚乙氧基化脂肪胺、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木质素磺酸钠、2，2’-二萘基甲烷-6，6’-二磺酸钠、二丁基萘磺酸钠，或油酰基经济牛酯酸钠(OleoylmethyltaurinsauresNatrium)，以及稀释剂或惰性物质。可湿性粉剂的制备是通过精细研磨除草活性物质，例如在常规的设备如锤磨、吹磨和气流磨中研磨，并在同时或随后将其与制剂助剂混合。
可乳化浓缩液的制备是通过在添加一种或多种离子型和/或非离子型表面活性剂的条件下将活性物质溶于有机溶剂中，有机溶剂例如：丁醇、环己酮、二甲基甲酰胺、二甲苯和高沸点的芳香化合物或烃类或有机溶剂的混合物。可使用的乳化剂的实例为：烷基芳基磺酸钙盐如十二烷基苯磺酸钙、或非离子型乳化剂，如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷/环氧乙烷缩合产物、烷基聚醚、脱水山梨醇酯、如脱水山梨醇脂肪酸酯或“聚氧乙烯脱水山梨醇酯，诸如聚氧乙烯脱水山梨醇脂肪酸酯。
粉剂的制备是通过将活性物质与细分离的固体物质研磨而制备，固体物质例如：滑石或天然粘土，如高岭土、膨润土、叶蜡石或硅藻土。
浓悬浮剂是以水或油为基础的。它们的制备是例如通过借取常规的球磨湿磨和必要时加入上述其它类型制剂中使用的表面活性剂来进行的。
乳液，例如水包油型乳液(EW)的制备例如：通过搅拌器、胶体磨和/或静电磨的方式，使用含水的有机溶剂和如果需要的表面活性剂来制备，表面活性剂如上述其它类型制剂中使用的表面活性剂。
颗粒剂的生产或是通过将活性物质喷布在吸收性、造粒惰性材料上，或是借助于粘合剂将活性物质的浓缩物涂敷在载体的表面，制备，载体如砂土、高岭土和造粒惰性材料，粘合剂例如聚乙烯醇、聚丙烯酸钠或矿物油。也可按常规的生产肥料颗粒的方法将活性物质造粒，如果需要可为与肥料的混合物。
水分散颗粒剂通常是通过常规的方法制备，如喷雾干燥、流化床造粒、平板(Teller)造粒、用高速混合器混合和不需要固体惰性载体的挤压。对于平板、流化床、挤压器和喷布颗粒的制备，可参见“Spary Drying Handbook”第3版，1979，G.GoodwinLtd.，”London；J.E.Browning，“Agglomeration”，Chemical andEngineering 1967，147等页；“Perry’s Chemical Engineer’sHandbook””，第5版，McGraw-Hill，New York 1973，8-57页。
对于作物保护组合物制剂的详细内容例如参见G.C.Klingman，“Weed Control sa a Science”，John Wiley和Sons，Inc.，New York，1961，81-96页和J.D.Freyer，S.A.Evans，“Weed ControlHandbook”，第5版，Blackweel ScientificPublications，Oxford，1968，101-103页。
本农用化学制剂通常含有0.1至99％重量和特别含有0.1至95％重量的式(I)活性物质。活性物质在可湿性粉剂中的浓度例如为大约10至90％重量；100％重量的剩余物由常规的制剂成分组成。在可乳化浓缩液的情况下，活性物质的浓度可为大约1至90％重量，优选5至80％重量。粉剂的制剂形式中含有1至30％重量，通常优选5-20％重量的活性物质，可喷雾液剂含有大约0.05至80，优选2至50％重量的活性成分。在水分散颗粒剂的情况下活性物质的含量部分的依赖于活性化合物为液体或固体和使用的造粒助剂、填料等。在水分散颗粒剂的情况下活性物质的含量为：例如1至95％重量，优选10至80％重量。
另外，已述及的活性物质的制剂如果适合可含有在各种情况下常规使用的粘着剂、湿润剂、分散剂、乳化剂、渗透剂、防腐剂、防冻剂、溶剂、填料、载体和着色剂、防泡剂、蒸发抑制剂和PH和粘度调节剂。
在混合制剂或桶混合物中的本发明活性物质的混用组合物中可使用，例如描述在如Weed Research 26，441-445(1986)或“ThePesticide Manual”，第9版，The British Crop ProtectionCouncil，1990/91，Bracknell，England，和其中所引文献描述的已知活性物质。可与式(I)化合物混用的文献中已知的除草剂的实例为下述活性物质(注意：化合物或是以其根据国际标准化组织(ISO)提供的通用名给出或是以化学名给出，如果需要还连带通用编码)：乙草胺、三氟羧草醚、苯草醚、氟草醚酯，即[[[1-[5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯基]-2-甲氧基亚乙基]氨基]氧]乙酸及其甲基酯、甲草胺、枯杀达、莠灭津、amidosulfuron、amitrol、AMS，即氨基磺酸铵、莎稗磷、黄草灵、莠去津、azimsulfurone(DPX-A8947)、叠氮津、燕麦灵、BAS516H，即5-氟-2-苯基-4H-3，1-苯并恶嗪-4-酮、草除灵、氟草胺、呋草黄、苄嘧磺隆、地散磷、灭草松、吡草酮、benzofluor、新燕灵、噻草隆、双丙氨酰膦、甲羧除草醚、除草定、溴丁酰草胺、杀草全、溴苯腈、bromuron、buminafos、busoxinone、丁草胺、草胺磷、丁烯草胺、草噻醚、地乐胺、丁草特、cafenstrole(CH-900)、卡草胺、碘草酮(ICI-A0051)、草毒死，即2-氯-N，N-二-2-丙烯基乙酰胺、草克死，即2-氯烯丙基二乙基二硫代氨基甲酸酯、氟硝醚、草灭平、chlorazifop-butyl、Chlormesulon(ICI-A0051)、氯溴隆、氟草灵、伐克草、氯甲丹、杀草敏、氯嘧磺隆、草枯醚、绿麦隆、枯草隆、氯苯胺灵、绿磺隆、敌草索、草克乐、恶庚草烷、醚磺隆、烯草酮、clodinafop及其酯衍生物(例如clodinafop-propargyl)、广灭灵、稗草胺、Cloproxydim、clopyralid、cumyluron(JC 940)、氰草津、环莠特、cyclosulfamuron(AC 104)、噻草酮、环莠隆、cyhalofop及其酯衍生物(例如丁基酯，DEH-112)、对草快、环草津、环唑草胺、daimuron、2，4-滴丁酸、茅草枯、异苯敌草、敌草净、燕麦敌、麦草畏、敌草腈、2，4-滴丙酸、禾草灵、及其酯如甲基禾草灵、安塔、枯莠隆、野燕枯、吡氟草胺、dimefuron、克草胺、戊草津、dimethenamide(SAN-582H)、敌苯达松、dimethipin、dimetrasulfuron、敌乐胺、地乐散、地乐硝酚、双苯酰草胺、杀草净、敌草快、氟硫草定、敌草隆、二硝甲酚、草止津、氟草酮，即5-氰基-1-(1，1-二甲基乙基)-N-甲基-1H-吡唑-4-甲酰胺、草藻灭、扑草灭、禾草畏、丁氟硝草、ethametsulfuron-methyl、噻二唑隆、乙嗪草酮、唑啶草、F5231，即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4，5-二氢-5-氧-1H-四唑-1-基]苯基]乙烷磺酰胺、ethoxyfen及其酯(例如乙基酯，HN-252)、etobenzanid(HW52)、2，4，5-滴丙酸、fenoxan、噁唑禾草灵和高噁唑禾草灵及其酯，例如fenoxaprop-P-ethyl和fenoxaprop-ethyl、fenoxydim、黄草隆、甲氟燕灵、啶嘧磺隆、吡氟禾草灵和精吡氟禾草灵及其酯，例如fluazifop-butyl和fluazifop-P-butyl、氟消草、flumetsulam、伏草隆、flumiclorac及其酯(例如苯基酯，S-23031)、flumioxazin(S-482)、flumipropyn、flupoxam(KNW-739)、fluorodifen、fluoroglycofen-ethyl、氟胺磺隆(UBIC-4243)、氟草同、fluroehloridone、fluroxypyr、flurtamone、氟磺胺草醚、膦铵素、氟呋草醚、草胺膦、草甘膦、halosaten、halosulfuron及其酯(例如甲基酯，NC-319)、吡氟乙草灵及其酯、吡氟氯禾灵(＝R-haloxyfop)及其酯、环嗪酮、咪草酯、灭草烟、灭草喹、及其盐如铵盐、imazethamethapyr、咪草胺、imazosulfuron、碘苯腈、丁环隆、异乐灵、异丙隆、异噁隆、异恶草胺、isoxapyrifop、卡草灵、克阔乐、环草定、利谷隆、二甲四氯、二甲四氯丁酸、二甲四氯丙酸、苯噻草胺、氟草磺、苯嗪草、吡草胺、噻唑隆、威百亩、灭草定、去草酮、methyldymron、metabenzuron、methobenzuron、秀谷隆、丙草胺、metosulam(XRD 511)、甲氧隆、赛克津、甲黄隆、抑草丹、禾草特、杀草利、二氢硫酸单脲、绿谷隆、灭草隆、MT128，即6-氯-N-(3-氯-2-丙烯基)-5-甲基-N-苯基-3-哒嗪胺(pyridazinamin)、MT 5959，即N-[3-氯-4-(1-甲基乙基)-苯基]-2-甲基戊酰胺、草萘胺、抑草生、NC310，即4-(2，4-二氯苯甲酰基)-1-甲基-5-苄基氧吡唑、草不隆、烟嘧磺隆、吡氯草胺、nitralin、除草醚、nitroflurofen、norflurazon、orbencarb、磺禾灵、恶霜灵(RP-020630)、恶草灵、氟消草醚、对草快、克草猛、胺硝草、氟草磺胺、敌克草、二苯乙草、毒莠定、哌草磷、piributicarb、pirifenop-butyl、丙草胺、氟嘧磺隆、环氰津、prodiamine、卡乐施、丙草止津、2，4，5-涕、扑草净、metryn、扑草胺、敌稗、喔草酯及其酯、扑灭津、苯胺灵、propisoehlor、拿草特、prosulfalin、杀草丹、prosulfuron(CGA-152005)、广草胺、pyrazolinate、杀草敏、吡嘧磺隆、苄草唑、达草酯、pyrithiobac(KIH-2031)、pyroxofop及其酯(即炔丙基酯)、二氯喹啉酸、喹草酸、quinofop及其酯衍生物、喹禾灵和quizalofop及其酯衍生物、即quizalofop-ethyl、quizalofop-P-tefuryl和-ethyl、renriduron、rimsulfuron(DPX-E 9636)、S275，即2-[4-氯-2-氟-5-(2-丙炔氧基)-苯基]4，5，6，7-私氢-2H-吲唑、密草通、烯禾定、环莠隆、西马津、西草净、氟萘草酯、即2-[[7-[2-氯-4-(三氟甲基)-苯氧基]-2-萘基]氧]丙酸及其甲基酯、sulfentrazon(FMC-97385，f-6285)、sultazuron、嘧磺隆、sulfosate(ICI-A0224)、三氟醋酸、tebutam(GCP-5544)、丁唑隆、特草定、牙根灵、猛杀草、甲氧去草净、特丁津、去草净、TFH450，即N，N-二乙基-3-[(2-乙基-6-甲基苯基)-磺酰基]-1H-1，2，4-三唑-1-甲酰胺、thenylchlor(NSK-850)、噻唑隆、thizopyr(Mon-13200)、thidiazimin(SN-124085)、嘧黄隆、杀草丹、丁草威、肟草酮、野麦畏、triasulfuron、triazofenamide、teibenuron-methyl、定草酯、tridiphane、草达津、氟乐灵、醚苯黄隆及其酯(例如甲基酯，DPX-66037)、三甲隆、tsitodef、灭草猛、WL 110547，即5-苯氧基-1-[3-(三氟甲基)-苯基]-1H-四唑、UBH-509、D-489、LS82-556、KPP-300、NC-324、NC-330、KH-218、DPX-N8189、SC-0774、DOWCO-535、DK-8910、V-53482、PP-600、MBH-001、KIH-9201、ET-751、KIH-6127和KIH-2023。
在使用时如果需要可以常规方式将市售形式的制剂稀释，例如用水稀释可湿性粉剂、可乳化浓缩液、分散和水分散颗粒剂，粉剂、用于土壤施用和撒播的颗粒剂以及可喷雾液剂，在使用前通常不需要用其它惰性物质稀释。
式(I)化合物的所需施用剂量可根据外部条件如温度、湿度、和使用除草剂的性质而变化。使用剂量可在很宽的范围内变化，例如0.001至10.0kg/ha或更多的活性物质；可是优选0.005至5kg/ha。A.化学实施例缩写：除非另外指明，百分比和量比指的是重量。
i.v.＝在减压条件下
h＝小时
实施例A1N-叔丁基-5-溴甲基-2-甲氧基羰基苯磺酰胺
将在420ml四氯甲烷中的54.8g(192mmol)的N-叔丁基-2-甲氧羰基-5-甲基苯磺酰胺在氮保护气下在加入36g(202mmol)的N-溴琥珀酰亚胺和0.5g的偶氮二异丁腈(AIBN)之后，在用日光灯照射的同时加热回流6-8小时。然后过滤溶液，并依次用亚硫酸氢钠溶液、碳酸氢钠溶液和水冲洗，用Na2SO4充分干燥并蒸发至干i.v.。从二异丙基醚/乙酸乙酯结晶剩余物，得到41.9g(57％)的N-叔丁基-5-溴甲基-2-甲氧基羰基苯磺酰胺，Fp.88-90℃。
实施例A2N-叔丁基-5-叠氮基甲基-2-甲氧基羰基苯磺酰胺
将25.5g(70mmol)的N-叔丁基-5-溴甲基-2-甲氧基羰基苯磺酰胺和5.9g(90mmol)的叠氮化钠在240ml乙醇中的溶液加热回流6小时。然后将溶液蒸发至干并用水/乙酸乙酯提取剩余物。用二异丙醚浸提粗产物，得到16.6g(72.5％)的N-叔丁基-5-叠氮基甲基-2-甲氧基羰基苯磺酰胺，Fp.63-65℃。
实施例A3N-叔丁基-5-氨基甲基-2-甲氧基羰基苯磺酰胺
将16.3g(50mmol)的N-叔丁基-5-叠氮基甲基-2-甲氧基羰基苯磺酰胺溶于300ml甲醇中并经Pd/C(5％)氢化。将混合物过滤并蒸发至干。将获得所粗产物通过硅胶粒洗脱纯化，用乙酸乙酯/甲醇4∶1作为洗脱液。获得粘稠油状的11.2g(74％)N-叔丁基-5-氨基甲基-2-甲氧基羰基苯磺酰胺。
1H NMR(100MHz，CDCl3)：δ＝1,25(s，9H，C(CH3)3)，
1,80 (bs，2H，NH2)，
3,95(s，3H，OCH3)，
4,00(s，2H，Ar-CH2)，
6,20(bs，1H，SO2NH)，
7,58(dd，1H，Ar-H)，
7,80(d，1H，Ar-H)，
8,10(dd，1H，Ar-H).
实施例A4N-叔丁基-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺
将0.63g(8mmol)的乙酰氯溶于10ml二氯甲烷中并滴加到冷却到0℃的、2.01g(6.7mmol)N-叔丁基-5-氨基甲基-2-甲氧基羰基苯磺酰胺和0.93ml(6.7mmol)三乙胺的30ml二氯甲烷溶液中，在室温下搅拌混合物2小时。用水洗涤反应溶液，干燥并蒸发至干i.v.。获得粘稠油状的2.1g(91％)的N-叔丁基-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺。
1H NMR(100MHz，CDCl3)：δ＝1,25(s，9H，C(CH3)3)，
2,05(s，3H，COCH3)，
3,95(s，3H，OCH3)，
4,50(s，2H，Ar-CH2)，
6,15(s，1H，SO2NH)，
6,38(bt，1H，NH)，
7,47(dd，1H，Ar-H)，
7,75(d，1H，Ar-H)，
7,95(dd，1H，Ar-H).
实施例A55-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺
将2.09g(6.1mmol)N-叔丁基-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺的25ml三氟乙酸溶液在室温下搅拌14小时，然后蒸发至干。从乙酸乙酯中结晶剩余物，得到1.33g(76％)的5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺，Fp.173-175℃。
实施例A6N-[4，6-(二甲氧基嘧啶-2-基)氨基羰基]-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺
将0.69g(4.54mmol)的1，8-二氮杂二环[5.4.0]十一-7-烯(DBU)在0℃加入到1.3g(4.54mmol)的5-乙酰氨基甲基-2-甲氧羰基苯磺酰胺和1.25g(4.54mmol)的N-(4，6-二甲氧基嘧啶-2-基)苯基氨基甲酸酯的20ml乙腈悬浮液中。在室温下2小时后，用水和乙醚稀释混合物，用盐酸酸化到pH 1-2，过滤出所得沉淀并干燥。获得1.32g(62％)的N-[4，6-(二甲氧基嘧啶-2-基)氨基羰基]-5-乙酰氨基甲基-2-甲氧基羰基苯磺酰胺，mp.149-150℃。
采用实施例A1-A6的类似方法，可获得例示于下述表1-4中的式(I)化合物(W＝O，A＝嘧啶基或三嗪基)。在表中：Fp.＝熔点℃Vb＝化合物号＝实施例号Me＝甲基＝CH3Et＝乙基Bu＝n-Bu＝n-丁基＝n-C4H9Ph＝苯基
表1
Vb. R1 R4 R5 R7 X Y Z Fp.℃1 CO2CH3 H CHO H OCH3 OCH3 CH 124-1252 ″ ″ ″ H OCH3 CH3 CH3 ″ ″ ″ H CH3 CH3 CH4 ″ ″ ″ H CH3 OC2H5 CH5 ″ ″ ″ H OCH3 OCH3 N6 ″ ″ ″ H OCH3 CH3 N7 ″ ″ ″ H OCH3 Cl CH8 ″ ″ ″ H OCF2H CH3 CH9 ″ ″ ″ H OCF2H OCF2H CH10 ″ ″ ″ H OCH3 Br CH11 ″ ″ ″ H OCH3 OC2H5 CH12 ″ ″ ″ H OCH3 SCH3 CH13 ″ ″ ″ H OCH3 OC2H5 N14 ″ ″ ″ H OCH3 OC3H7 CH15 ″ ″ ″ H CH3 Cl CH16 ″ ″ ″ H Cl OC2H5 CH17 ″ ″ ″ H OC2H5 OC2H5 CH18 ″ ″ ″ H C2H5 OCH3 CH19 ″ ″ ″ H CF3 OCH3 CH20 ″ ″ ″ H OCH2CF3 CH3 CH21 ″ ″ ″ H OCH2CF3 OCH3 CH22 ″ ″ ″ H OCH2CF3 OCH2CF3 CH23 ″ ″ ″ H OCH2CF3 OCH3 N Vb. R1 R4 R5 R7 X Y Z Fp.C24 ″ ″ ″ H OCH3 CH(OCH3)2 CH25 ″ ″ ″ CH3 OCH3 OCH3 CH26 ″ ″ ″ CH3 OCH3 CH3 N27 ″ H COCH3 H OCH3 OCH3 CH 149-15028 ″ ″ ″ H OCH3 CH3 CH29 ″ ″ ″ H CH3 CH3 CH30 ″ ″ ″ H CH3 OC2H5 CH31 ″ ″ ″ H OCH3 OCH3 N32 ″ ″ ″ H OCH3 CH3 N33 ″ ″ ″ H OCH3 Cl CH34 ″ ″ ″ H OCF2H CH3 CH35 ″ ″ ″ H OCF2H OCF2H CH36 ″ ″ ″ H OCH3 Br CH37 ″ ″ ″ H OCH3 OC2H5 CH38 ″ ″ ″ H OCH3 SCH3 CH39 ″ ″ ″ H OCH3 OC2H5 N40 ″ ″ ″ H OCH3 OC3H7 CH41 ″ ″ ″ H CH3 Cl CH42 ″ ″ ″ H Cl OC2H5 CH43 ″ ″ ″ H OC2H5 OC2H5 CH44 ″ ″ ″ H C2H5 OCH3 CH45 ″ ″ ″ H CF3 OCH3 CH46 ″ ″ ″ H OCH2CF3 CH3 CH47 ″ ″ ″ H OCH2CF3 OCH3 CH48 ″ ″ ″ H OCH2CF3 OCH2CF3 CH49 ″ ″ ″ H OCH2CF3 OCH3 N50 ″ ″ ″ H OCH3 CH(OCH3)2 CH51 ″ ″ ″ CH3 OCH3 OCH3 CH52 ″ ″ ″ CH3 OCH3 CH3 N53 ″ CH3 CHO H OCH3 OCH3 CH 171-17554 ″ ″ ″ H OCH3 CH3 CH 135-14055 ″ ″ ″ H CH3 CH3 CH 123-12656 ″ ″ ″ H CH3 OC2H5 CH57 ″ ″ ″ H OCH3 OCH3 N58 ″ ″ ″ H OCH3 CH3 N 105 Vb. R1 R4 R5 R7 X Y Z Fp.C59 ″ ″ ″ H OCH3 Cl CH 125-13060 ″ ″ ″ H OCF2H CH3 CH61 ″ ″ ″ H OCF2H OCF2H CH62 ″ ″ ″ H OCH3 Br CH63 ″ ″ ″ H OCH3 OC2H5 CH64 ″ ″ ″ H OCH3 SCH3 CH65 ″ ″ ″ H OCH3 OC2H5 N66 ″ ″ ″ H OCH3 OC3H7 CH67 ″ ″ ″ H CH3 Cl CH68 ″ ″ ″ H Cl OC2H5 CH69 ″ ″ ″ H OC2H5 OC2H5 CH70 ″ ″ ″ H C2H5 OCH3 CH71 ″ ″ ″ H CF3 OCH3 CH72 ″ ″ ″ H OCH2CF3 CH3 CH73 ″ ″ ″ H OCH2CF3 OCH3 CH74 ″ ″ ″ H OCH2CF3 OCH2CF3 CH75 ″ ″ ″ H OCH2CF3 OCH3 N76 ″ ″ ″ H OCH3 CH(OCH3)2 CH77 ″ ″ ″ CH3 OCH3 OCH3 CH78 ″ ″ ″ CH3 OCH3 CH3 N79 ″ CH3 COCH3 H OCH3 OCH2 CH 146-14980 ″ ″ ″ H OCH3 CH3 CH81 ″ ″ ″ H CH3 CH3 CH82 ″ ″ ″ H CH3 OC2H5 CH83 ″ ″ ″ H OCH3 OCH3 N84 ″ ″ ″ H OCH3 CH3 N85 ″ ″ ″ H OCH3 Cl CH86 ″ ″ ″ H OCF2H CH3 CH87 ″ ″ ″ H OCF2H OCF2H CH88 ″ ″ ″ H OCH3 Br CH89 ″ ″ ″ H OCH3 OC2H5 CH90 ″ ″ ″ H OCH3 SCH3 CH91 ″ ″ ″ H OCH3 OC2H5 N92 ″ ″ ″ H OCH3 OC3H7 CH93 ″ ″ ″ H CH3 Cl CH Vb. R1 R4 R5 R7 X Y Z Fp.℃94 ″ ″ ″ H Cl OC2H5 CH95 ″ ″ ″ H OC2H5 OC2H5 CH96 ″ ″ ″ H C2H5 OCH3 CH97 ″ ″ ″ H CF3 OCH3 CH98 ″ ″ ″ H OCH2CF3 CH3 CH99 ″ ″ ″ H OCH2CF3 OCH3 CH100 ″ ″ ″ H OCH2CF3 OCH2CF3 CH101 ″ ″ ″ H OCH2CF3 OCH3 N102 ″ ″ ″ H OCH3 CH(OCH3)2 CH103 ″ ″ ″ CH3 OCH3 OCH3 CH104 ″ ″ ″ CH3 OCH3 CH3 N105 ″ H SO2CH3H OCH3 OCH3 CH 192-194106 ″ ″ ″ H OCH3 CH3 CH107 ″ ″ ″ H CH3 CH3 CH108 ″ ″ ″ H OCH3 OCH3 N109 ″ ″ ″ H OCH3 CH3 N110 ″ ″ ″ H OC2H5 NHCH3 N111 ″ ″ ″ CH3 OCH3 OCH3 CH112 ″ ″ ″ CH3 OCH3 CH3 N113 ″ CH3 SO2CH3H OCH3 OCH3 CH 107-109114 ″ ″ ″ H OCH3 CH3 CH115 ″ ″ ″ H CH3 CH3 CH116 ″ ″ ″ H OCH3 OCH3 N117 ″ ″ ″ H OCH3 CH3 N118 ″ ″ ″ H OC2H5 NHCH3 N119 ″ ″ ″ CH3 OCH3 OCH3 CH120 ″ ″ ″ CH3 OCH3 CH3 N121 ″ OH CHO H OCH3 OCH3 CH122 ″ ″ ″ H OCH3 CH3 CH123 ″ ″ ″ H CH3 CH3 CH124 ″ ″ ″ H OCH3 OCH3 N125 ″ ″ ″ H OCH3 CH3 N126 ″ ″ ″ H OC2H5 NHCH3 N127 ″ ″ ″ CH3 OCH3 OCH3 CH128 ″ ″ ″ CH3 OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃129 ″ OCH3 CHO H OCH3 OCH3 CH 142-145130 ″ ″ ″ H OCH3 CH3 CH131 ″ ″ ″ H CH3 CH3 CH132 ″ ″ ″ H OCH3 OCH3 N133 ″ ″ ″ H OCH3 CH3 N134 ″ ″ ″ H OC2H5 NHCH3 N135 ″ ″ ″ CH3 OCH3 OCH3 CH136 ″ ″ ″ CH3 OCH3 CH3 N137 ″ OH COCH3 H OCH3 OCH3 CH138 ″ ″ ″ H OCH3 CH3 CH139 ″ ″ ″ H CH3 CH3 CH140 ″ ″ ″ H OCH3 OCH3 N141 ″ ″ ″ H OCH3 CH3 N142 ″ ″ ″ H OC2H5 NHCH3 N143 ″ ″ ″ CH3 OCH3 OCH3 CH144 ″ ″ ″ CH3 OCH3 CH3 N145 ″ OCH3 COCH3 H OCH3 OCH3 CH 195-196146 ″ ″ ″ H OCH3 CH3 CH147 ″ ″ ″ H CH3 CH3 CH148 ″ ″ ″ H OCH3 OCH3 N149 ″ ″ ″ H OCH3 CH3 N150 ″ ″ ″ H OC2H5 NHCH3 N151 ″ ″ ″ CH3 OCH3 OCH3 CH152 ″ ″ ″ CH3 OCH3 CH3 N153 ″ H COC2H5 H OCH3 OCH3 CH 150-152154 ″ ″ ″ H OCH3 CH3 CH155 ″ ″ ″ H OCH3 OCH3 N156 ″ ″ ″ H OCH3 CH3 N157 ″ CH3 ″ H OCH3 OCH3 CH158 ″ ″ ″ H OCH3 CH3 CH159 ″ ″ ″ H OCH3 OCH3 N160 ″ ″ ″ H OCH3 CH3 N161 ″ H COCH2OCH3 H OCH3 OCH3 CH162 ″ ″ ″ H OCH3 CH3 CH163 ″ ″ ″ H OCH3 OCH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃164 ″ ″ ″ H OCH3 CH3 N165 ″ CH3 ″ H OCH3 OCH3 CH166 ″ ″ ″ H OCH3 CH3 CH167 ″ ″ ″ H OCH3 OCH3 N168 ″ ″ ″ H OCH3 CH3 N169 ″ H COCO2C2H5 H OCH3 OCH3 CH170 ″ ″ ″ H OCH3 CH3 CH171 ″ ″ ″ H OCH3 OCH3 N172 ″ ″ ″ H OCH3 CH3 N173 ″ CH3 ″ H OCH3 OCH3 CH174 ″ ″ ″ H OCH3 CH3 CH175 ″ ″ ″ H OCH3 OCH3 N176 ″ ″ ″ H OCH3 CH3 N177 ″ H COCF3 H OCH3 OCH3 CH 158178 ″ ″ ″ H OCH3 CH3 CH179 ″ ″ ″ H OCH3 OCH3 N180 ″ ″ ″ H OCH3 CH3 N181 ″ CH3 ″ H OCH3 OCH3 CH 144-147182 ″ ″ ″ H OCH3 CH3 CH183 ″ ″ ″ H OCH3 OCH3 N184 ″ ″ ″ H OCH3 CH3 N185 ″ H COOCH3 H OCH3 OCH3 CH 160-161186 ″ ″ ″ H OCH3 CH3 CH187 ″ ″ ″ H OCH3 OCH3 N188 ″ ″ ″ H OCH3 CH3 N189 ″ CH3 ″ H OCH3 OCH3 CH 157-159190 ″ ″ ″ H OCH3 CH3 CH191 ″ ″ ″ H OCH3 OCH3 N192 ″ ″ ″ H OCH3 CH3 N193 ″ H CONHC2H5 H OCH3 OCH3 CH194 ″ ″ ″ H OCH3 CH3 CH195 ″ ″ ″ H OCH3 OCH3 N196 ″ ″ ″ H OCH3 CH3 N197 ″ CH3 ″ H OCH3 OCH3 CH198 ″ ″ ″ H OCH3 CH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃199 ″ ″ ″ H OCH3 OCH3 N200 ″ ″ ″ H OCH3 CH3 N201 ″ H CSNHC2H5 H OCH3 OCH3 CH202 ″ ″ ″ H OCH3 CH3 CH203 ″ ″ ″ H OCH3 OCH3 N204 ″ ″ ″ H OCH3 CH3 N205 ″ CH3 ″ H OCH3 OCH3 CH206 ″ ″ ″ H OCH3 CH3 CH207 ″ ″ ″ H OCH3 OCH3 N208 ″ ″ ″ H OCH3 CH3 N209 ″ H SO2NHCH3 H OCH3 OCH3 CH210 ″ ″ ″ H OCH3 CH3 CH211 ″ ″ ″ H OCH3 OCH3 N212 ″ ″ ″ H OCH3 CH3 N213 ″ CH3 ″ H OCH3 OCH3 CH 171-173214 ″ ″ ″ H OCH3 CH3 CH215 ″ ″ ″ H OCH3 OCH3 N216 ″ ″ ″ H OCH3 CH3 N217 ″ H SO2N(CH3)2 H OCH3 OCH3 CH 162218 ″ ″ ″ H OCH3 CH3 CH219 ″ ″ ″ H OCH3 OCH3 N220 ″ ″ ″ H OCH3 CH3 N221 ″ CH3 ″ H OCH3 OCH3 CH 127-129222 ″ ″ ″ H OCH3 CH3 CH223 ″ ″ ″ H OCH3 OCH3 N224 ″ ″ ″ H OCH3 CH3 N225 ″-CH2CH2CH2CO- H OCH3 OCH3 CH226 ″ ″ H OCH3 CH3 CH227 ″ ″ H OCH3 OCH3 N228 ″ ″ H OCH3 CH3 N229 ″-CH2CH2CH2SO2- H OCH3 OCH3 CH230 ″ ″ H OCH3 CH3 CH231 ″ ″ H OCH3 OCH3 N232 ″ ″ H OCH3 CH3 N233 ″-CH2CH2CH2CH2CO- H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃234 ″ ″ H OCH3 CH3 CH235 ″ ″ H OCH3 OCH3 N236 ″ ″ H OCH3 CH3 N237 ″ -CH2CH2CH2CH2SO2- H OCH3 OCH3 CH238 ″ ″ H OCH3 CH3 CH239 ″ ″ H OCH3 OCH3 N240 ″ ″ H OCH3 CH3 N241 ″ -CH2CH2OCH2CH2- H OCH3 OCH3 CH242 ″ ″ H OCH3 CH3 CH243 ″ ″ H OCH3 OCH3 N244 ″ ″ H OCH3 CH3 N245 ″ H COC3H7 H OCH3 OCH3 CH246 ″ ″ ″ H OCH3 CH3 CH247 ″ ″ ″ H OCH3 OCH3 N248 ″ ″ ″ H OCH3 CH3 N249 ″ CH3 ″ H OCH3 OCH3 CH250 ″ ″ ″ H OCH3 CH3 CH251 ″ ″ ″ H OCH3 OCH3 N252 ″ ″ ″ H OCH3 CH3 N253 ″ H COCH2Cl H OCH3 OCH3 CH 144-145254 ″ ″ ″ H OCH3 CH3 CH255 ″ ″ ″ H OCH3 OCH3 N256 ″ ″ ″ H OCH3 CH3 N257 ″ CH3 ″ H OCH3 OCH3 CH 138-140258 ″ ″ ″ H OCH3 CH3 CH259 ″ ″ ″ H OCH3 OCH3 N260 ″ ″ ″ H OCH3 CH3 N261 ″ H COCHCl2 H OCH3 OCH3 CH262 ″ ″ ″ H OCH3 CH3 CH263 ″ ″ ″ H OCH3 OCH3 N264 ″ ″ ″ H OCH3 CH3 N265 ″ CH3 ″ H OCH3 OCH3 CH266 ″ ″ ″ H OCH3 CH3 CH267 ″ ″ ″ H OCH3 OCH3 N268 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃269 ″ H COCCl3 H OCH3 OCH3 CH270 ″ ″ ″ H OCH3 CH3 CH271 ″ ″ ″ H OCH3 OCH3 N272 ″ ″ ″ H OCH3 CH3 N273 ″ CH3 ″ H OCH3 OCH3 CH274 ″ ″ ″ H OCH3 CH3 CH275 ″ ″ ″ H OCH3 OCH3 N276 ″ ″ ″ H OCH3 CH3 N277 ″ H COCH＝CH2 H OCH3 OCH3 CH278 ″ ″ ″ H OCH3 CH3 CH279 ″ ″ ″ H OCH3 OCH3 N280 ″ ″ ″ H OCH3 CH3 N281 ″ CH3 ″ H OCH3 OCH3 CH282 ″ ″ ″ H OCH3 CH3 CH283 ″ ″ ″ H OCH3 OCH3 N284 ″ ″ ″ H OCH3 CH3 N285 ″ H COC＝CH H OCH3 OCH3 CH286 ″ ″ ″ H OCH3 CH3 CH287 ″ ″ ″ H OCH3 OCH3 N288 ″ ″ ″ H OCH3 CH3 N289 ″ CH3 ″ H OCH3 OCH3 CH290 ″ ″ ″ H OCH3 CH3 CH291 ″ ″ ″ H OCH3 OCH3 N292 ″ ″ ″ H OCH3 CH3 N293 ″ H COC6H5 H OCH3 OCH3 CH294 ″ ″ ″ H OCH3 CH3 CH295 ″ ″ ″ H OCH3 OCH3 N296 ″ ″ ″ H OCH3 CH3 N297 ″ CH3 ″ H OCH3 OCH3 CH298 ″ ″ ″ H OCH3 CH3 CH299 ″ ″ ″ H OCH3 OCH3 N300 ″ ″ ″ H OCH3 CH3 N301 ″ SO2C6H5 SO2C6H5H OCH3 OCH3 CH302 ″ ″ ″ H OCH3 CH3 CH303 ″ ″ ″ H OCH3 OCH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃304 ″ ″ ″ H OCH3 CH3 N305 ″ SO2CH3 SO2CH3 H OCH3 OCH3 CH306 ″ ″ ″ H OCH3 CH3 CH307 ″ ″ ″ H OCH3 OCH3 N308 ″ ″ ″ H OCH3 CH3 N309 ″ H COCH2Br H OCH3 OCH3 CH310 ″ ″ ″ H OCH3 CH3 N311 ″ CH3 ″ H OCH3 OCH3 CH312 ″ ″ ″ H OCH3 CH3 N313 ″ H COCH2F H OCH3 OCH3 CH314 ″ ″ ″ H OCH3 CH3 N315 ″ CH3 ″ H OCH3 OCH3 CH316 ″ ″ ″ H OCH3 CH3 N317 ″ H COCH2C＝CH H OCH3 OCH3 CH318 ″ ″ ″ H OCH3 CH3 N319 ″ CH3 ″ H OCH3 OCH3 CH320 ″ ″ ″ H OCH3 CH3 N321 ″ H COCO2CH3 H OCH3 OCH3 CH322 ″ ″ ″ H OCH3 CH3 N323 ″ CH3 ″ H OCH3 OCH3 CH324 ″ ″ ″ H OCH3 CH3 N325 ″ H CO2C2H5 H OCH3 OCH3 CH326 ″ ″ ″ H OCH3 CH3 N327 ″ CH3 ″ H OCH3 OCH3 CH328 ″ ″ ″ H OCH3 CH3 N329 ″ H COSCH3 H OCH3 OCH3 CH330 ″ ″ ″ H OCH3 CH3 N331 ″ CH3 ″ H OCH3 OCH3 CH332 ″ ″ ″ H OCH3 CH3 N333 ″ H CSOCH3 H OCH3 OCH3 CH334 ″ ″ ″ H OCH3 CH3 N335 ″ CH3 ″ H OCH3 OCH3 CH336 ″ ″ ″ H OCH3 CH3 N337 ″ H CSSCH3 H OCH3 OCH3 CH338 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃339 ″ CH3 ″ H OCH3 OCH3 CH340 ″ ″ ″ H OCH3 CH3 N341 ″ H COCH(CH3)2 H OCH3 OCH3 CH342 ″ ″ ″ H OCH3 CH3 N343 ″ CH3 ″ H OCH3 OCH3 CH344 ″ ″ ″ H OCH3 CH3 N345 ″ H COC(CH3)3 H OCH3 OCH3 CH346 ″ ″ ″ H OCH3 CH3 N347 ″ CH3 ″ H OCH3 OCH3 CH348 ″ ″ ″ H OCH3 CH3 N349 ″ H CO-环丙基 H OCH3 OCH3 CH350 ″ ″ ″ H OCH3 CH3 N351 ″ CH3 ″ H OCH3 OCH3 CH352 ″ ″ ″ H OCH3 CH3 N353 ″ H CO环丁基 H OCH3 OCH3 CH354 ″ ″ ″ H OCH3 CH3 N355 ″ CH3 ″ H OCH3 OCH3 CH356 ″ ″ ″ H OCH3 CH3 N357 ″ H CO-环戊基 H OCH3 OCH3 CH358 ″ ″ ″ H OCH3 CH3 N359 ″ CH3 ″ H OCH3 OCH3 CH360 ″ ″ ″ H OCH3 CH3 N361 ″ H CO-环己基 H OCH3 OCH3 CH362 ″ ″ ″ H OCH3 CH3 N363 ″ CH3 ″ H OCH3 OCH3 CH364 ″ ″ ″ H OCH3 CH3 N365 ″ H CONHCH2CH2Cl H OCH3 OCH3 CH366 ″ ″ ″ H OCH3 CH3 N367 ″ CH3 ″ H OCH3 OCH3 CH368 ″ ″ ″ H OCH3 CH3 N369 ″ H CSNHCH2CH2Cl H OCH3 OCH3 CH370 ″ ″ ″ H OCH3 CH3 N371 ″ CH3 ″ H OCH3 OCH3 CH372 ″ ″ ″ H OCH3 CH3 N373 ″ H CONH-n-C4H9 H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃374 ″ ″ ″ H OCH3 CH3 N375 ″ CH3 ″ H OCH3 OCH3 CH376 ″ ″ ″ H OCH3 CH3 N377 ″ H CSNHCH3 H OCH3 OCH3 CH378 ″ ″ ″ H OCH3 CH3 N379 ″ CH3 ″ H OCH3 OCH3 CH380 ″ ″ ″ H OCH3 CH3 N381 ″ H CSNHCH2CH＝CH2 H OCH3 OCH3 CH382 ″ ″ ″ H OCH3 CH3 N383 ″ CH3 ″ H OCH3 OCH3 CH384 ″ ″ ″ H OCH3 CH3 N385 ″ CH3 CSNHCH2COCH3 H OCH3 OCH3 CH386 ″ ″ ″ H OCH3 CH3 N387 ″ CH3 CSNHCH2COC2H5 H OCH3 OCH3 CH388 ″ ″ ″ H OCH3 CH3 N389 ″ CH3 CONHCH2COCH3 H OCH3 OCH3 CH390 ″ ″ ″ H OCH3 CH3 N391 ″ CH3 CONHCH2COC2H5 H OCH3 OCH3 CH392 ″ ″ ″ H OCH3 CH3 N393 ″ -CONHCH2CO- H OCH3 OCH3 CH394 ″ ″ H OCH3 CH3 N395 ″ H SO2CH2F H OCH3 OCH3 CH396 ″ ″ ″ H OCH3 CH3 N397 ″ CH3 ″ H OCH3 OCH3 CH398 ″ ″ ″ H OCH3 CH3 N399 ″ H SO2CF3 H OCH3 OCH3 CH400 ″ ″ ″ H OCH3 CH3 N401 ″ CH3 ″ H OCH3 OCH3 CH402 ″ ″ ″ H OCH3 CH3 N403 ″ H SO2C2H5 H OCH3 OCH3 CH404 ″ ″ ″ H OCH3 CH3 N405 ″ CH3 ″ H OCH3 OCH3 CH406 ″ ″ ″ H OCH3 CH3 N407 ″ H SO2-n-C3H7 H OCH3 OCH3 CH408 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃409 ″ CH3 ″ H OCH3 OCH3 CH410 ″ ″ ″ H OCH3 CH3 N411 ″ OH COC2H5 H OCH3 OCH3 CH412 ″ ″ ″ H OCH3 CH3 N413 ″ OCH3 ″ H OCH3 OCH3 CH414 ″ ″ ″ H OCH3 CH3 N415 ″ OH COCH2Cl H OCH3 OCH3 CH416 ″ ″ ″ H OCH3 CH3 N417 ″ OCH3 ″ H OCH3 OCH3 CH418 ″ ″ ″ H OCH3 CH3 N419 ″ OH COCF3 H OCH3 OCH3 CH420 ″ ″ ″ H OCH3 CH3 N421 ″ OCH3 ″ H OCH3 OCH3 CH 159-161422 ″ ″ ″ H OCH3 CH3 N423 ″ OH COCH2OCH3 H OCH3 OCH3 CH424 ″ ″ ″ H OCH3 CH3 N425 ″ OCH3 ″ H OCH3 OCH3 CH 130-131426 ″ ″ ″ H OCH3 CH3 N427 ″ OH COCO2C2H5 H OCH3 OCH3 CH428 ″ ″ ″ H OCH3 CH3 N429 ″ OCH3 ″ H OCH3 OCH3 CH 158-159430 ″ ″ ″ H OCH3 CH3 N431 ″ OH COOCH3 H OCH3 OCH3 CH432 ″ ″ ″ H OCH3 CH3 N433 ″ OCH3 ″ H OCH3 OCH3 CH 137-138434 ″ ″ ″ H OCH3 CH3 N435 ″ OH Cyclopropyl H OCH3 OCH3 CH436 ″ ″ ″ H OCH3 CH3 N437 ″ OCH3 ″ H OCH3 OCH3 CH 118-120438 ″ ″ ″ H OCH3 CH3 N439 ″ OH COC6H5 H OCH3 OCH3 CH440 ″ ″ ″ H OCH3 CH3 N441 ″ OCH3 ″ H OCH3 OCH3 CH442 ″ ″ ″ H OCH3 CH3 N443 ″ OH COCH(CH3)2 H OCH3 OCH3 CH Vb. R1 R4 R5 R7X Y Z Fp.℃444 ″ ″ ″ H OCH3 CH3 N445 ″ OCH3 ″ H OCH3 OCH3 CH 126-128446 ″ ″ ″ H OCH3 CH3 N447 ″ OH COCH＝CH2 H OCH3 OCH3 CH448 ″ ″ ″ H OCH3 CH3 N449 ″ OCH3 ″ H OCH3 OCH3 CH450 ″ ″ ″ H OCH3 CH3 N451 ″ OH COC＝CH H OCH3 OCH3 CH452 ″ ″ ″ H OCH3 CH3 N453 ″ OCH3 ″ H OCH3 OCH3 CH454 ″ ″ ″ H OCH3 CH3 N455 ″ OH SO2CH3 H OCH3 OCH3 CH456 ″ ″ ″ H OCH3 CH3 N457 ″ OCH3 ″ H OCH3 OCH3 CH 146-148458 ″ ″ ″ H OCH3 CH3 N459 ″ OH SO2NHCH3 H OCH3 OCH3 CH460 ″ ″ ″ H OCH3 CH3 N461 ″ OCH3 ″ H OCH3 OCH3 CH 179-180462 ″ ″ ″ H OCH3 CH3 N463 ″ OH SO2N(CH3)2H OCH3 OCH3 CH464 ″ ″ ″ H OCH3 CH3 N465 ″ OCH3 ″ H OCH3 OCH3 CH 179-180466 ″ ″ ″ H OCH3 CH3 N467 ″ C2H5CHO H OCH3 OCH3 CH 168-170468 ″ ″ ″ H OCH3 CH3 N469 ″ ″ COCH3 H OCH3 OCH3 CH470 ″ ″ ″ H OCH3 CH3 N471 ″ ″ 环丙基 H OCH3 OCH3 CH472 ″ ″ ″ H OCH3 CH3 N473 ″ ″ COCH2Cl H OCH3 OCH3 CH474 ″ ″ ″ H OCH3 CH3 N475 ″ ″ COCF3 H OCH3 OCH3 CH476 ″ ″ ″ H OCH3 CH3 N477 ″ ″ COOCH3 H OCH3 OCH3 CH478 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃479 ″ ″ COC6H5 H OCH3 OCH3 CH480 ″ ″ ″ H OCH3 CH3 N481 ″ ″ CONHC2H5 H OCH3 OCH3 CH482 ″ ″ ″ H OCH3 CH3 N483 ″ ″ CSNHC2H5 H OCH3 OCH3 CH484 ″ ″ ″ H OCH3 CH3 N485 ″ ″ SO2CH3 H OCH3 OCH3 CH 154-155486 ″ ″ ″ H OCH3 CH3 N487 ″ ″ SO2NHCH3 H OCH3 OCH3 CH 150-152488 ″ ″ ″ H OCH3 CH3 N489 ″ ″ SO2N(CH3)2H OCH3 OCH3 CH490 ″ ″ ″ H OCH3 CH3 N491 ″ ″ SO2C6H5 H OCH3 OCH3 CH492 ″ ″ ″ H OCH3 CH3 N493 CO2C2H5 H CHO H OCH3 OCH3 CH494 ″ ″ ″ H OCH3 CH3 N495 ″ ″ COCH3 H OCH3 OCH3 CH496 ″ ″ ″ H OCH3 CH3 N497 ″ ″ SO2CH3 H OCH3 OCH3 CH498 ″ ″ ″ H OCH3 CH3 N499 ″ CH3 CHO H OCH3 OCH3 CH500 ″ ″ ″ H OCH3 CH3 N501 ″ ″ COCH3 H OCH3 OCH3 CH502 ″ ″ ″ H OCH3 CH3 N503 ″ ″ SO2CH3 H OCH3 OCH3 CH504 ″ ″ ″ H OCH3 CH3 N505 ″ C2H5 CHO H OCH3 OCH3 CH506 ″ ″ ″ H OCH3 CH3 N507 ″ ″ COCH3 H OCH3 OCH3 CH508 ″ ″ ″ H OCH3 CH3 N509 ″ ″ SO2CH3 H OCH3 OCH3 CH510 ″ ″ ″ H OCH3 CH3 N511 ″ OH CHO H OCH3 OCH3 CH512 ″ ″ ″ H OCH3 CH3 N513 ″ ″ COCH3 H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃514 ″ ″ ″ H OCH3 CH3 N515 ″ ″ SO2CH3 H OCH3 OCH3 CH516 ″ ″ ″ H OCH3 CH3 N517 ″ OCH3 CHO H OCH3 OCH3 CH518 ″ ″ ″ H OCH3 CH3 N519 ″ ″ COCH3 H OCH3 OCH3 CH520 ″ ″ ″ H OCH3 CH3 N521 CO2-n-Bu H CHO H OCH3 OCH3 CH522 CON(CH3)2 CH3 CHO H OCH3 CH3 N523 CONHCH3 H CHO H OCH3 OCH3 CH524 COSCH3 CH3 COCH3 H OCH3 CH3 N525 CO2CH3 n-Bu CHO H OCH3 OCH3 CH526 ″ ″ ″ H OCH3 CH3 N527 ″ H ″ H OCH2CF3 N(CH3)2 N528 ″ CH3 ″ H ″ ″ N529 ″ H COCH3 H ″ ″ ″530 ″ CH3 ″ H ″ ″ ″531 ″ ″ SO2CH3 H OCH3 OCH3 CH532 ″ ″ ″ H OCH3 CH3 N533 CO2CH3 
H OCH3 OCH3 CH534 ″ ″ H OCH3 CH3 N535 CO2CH3 CH3 CHO H OCH3 OCH3 CH 钠盐236-238536 CO2CH3 H SO2CH3 H OCH3 OCH3 CH 钠盐170-173537 CO2CH3 CH3 SO2CH3 H OCH3 OCH3 CH 钠盐191538 CO2CH3 OCH3 CHO H OCH3 OCH3 CH 钠盐215-216539 CO2CH3 OCH3 COCH3 H OCH3 OCH3 CH 钠盐 Vb. R1 R4 R5 R7 X Y Z Fp.℃540 CO2CH3 H COOCH3 H OCH3 OCH3 CH 钠盐203-205541 CO2CH3 CH3 SO2N(CH3)2 H OCH3 OCH3 CH 钠盐122542 CO2CH3 CH3 CONHEt H OCH3 OCH3 CH 钠盐190-192543 CO2CH3 CH3 CONHEt H OCH3 OCH3 CH 150-152544 CO2CH3 CH3 CONHEt H OCH3 CH3 N545 CO2CH3 H CONHEt H OCH3 OCH3 CH546 CO2CH3 H CONHEt H OCH3 CH3 N547 CO2CH3 -CO-CH2CH2-CO- H OCH3 OCH3 CH 220-221548 CO2CH3 -CO-CH2CH2-CO- H OCH3 OCH3 N549 CO2CH3 -CO-CH2CH2-CO- H OCH3 CH3 CH550 CO2CH3 -CO-CH2CH2-CO- H OCH3 CH3 N551 CO2CH3 -CO-CH2CH2-CO- H OCH3 OCH3 CH 钠盐210-212552 CO2CH3 OCH3 COCF3 H OCH3 OCH3 CH 钠盐228-229553 CO2CH3 OCH3 COOCH3 H OCH3 OCH3 CH 钠盐184-185554 CO2CH3 OCH3 Cyclopropyl H OCH3 OCH3 CH 钠盐216555 CO2CH3 OCH3 SO2CH3 H OCH3 OCH3 CH 钠盐183-185556 CO2CH3 C2H5 CHO H OCH3 OCH3 CH 钠盐237-239557 CO2CH3 C2H5 Cyclopropyl H OCH3 OCH3 CH 钠盐178-180558 CO2CH3 C2H5 COCCl3 H OCH3 OCH3 CH 109-111559 CO2CH3 C2H5 COCCl3 H OCH3 OCH3 CH 钠盐174-176560 CO2CH3 C2H5 COCCl3 H OCH3 CH3 N561 CO2CH3 C2H5 COCOOCH3 H OCH3 CH3 N562 CO2CH3 C2H5 COCOOCH3 H OCH3 OCH3 CH 138-140563 CO2CH3 C2H5 COCH2OCH3 H OCH3 OCH3 CH 121-123Vb. R1 R4 R5 R7 X Y Z Fp.℃564 CO2CH3 C2H5 COCH2OCH3 H OCH3 CH3 N565 CO2CH3 C2H5 SO2CH3 H OCH3 OCH3 CH 154-155566 CO2CH3 C2H5 SO2CH3 H OCH3 OCH3 CH 钠盐161567 CO2CH3 C2H5 SO2NHCH3 H OCH3 OCH3 CH 150-152568 CO2CH3 C2H5 SO2NHCH3 H OCH3 OCH3 CH 钠盐165-168569 CO2CH3 OC2H5 SO2CH3 H OCH3 OCH3 CH 163-164570 CO2CH3 OC2H5 SO2CH3 H OCH3 OCH3 CH 钠盐166-168571 CO2CH3 OC2H5 CHO H OCH3 OCH3 CH 165-166572 CO2CH3 OC2H5 CHO H OCH3 OCH3 CH 钠盐207-208573 CO2CH3 OCH3 CONHPh H OCH3 OCH3 CH 178-179574 CO2CH3 OCH3 CONHEt H OCH3 OCH3 CH 155-157575 CO2CH3 OCH3 COCCl3 H OCH3 OCH3 CH 165-168576 CO2CH3 OCH3 COCCl3 H OCH3 OCH3 CH 钠盐100577 CO2CH3 OCH3 COCHCl2 H OCH3 OCH3 CH 145-150578 CO2CH3 OCH3 COCHCl2 H OCH3 OCH3 CH 钠盐235表2
Vb. R1 R4 R5 R7 X Y Z Fp.℃1 CO2CH3 H CHO H OCH3 OCH3 CH 142-1442 ″ ″ ″ H OCH3 CH3 CH3 ″ ″ ″ H CH3 CH3 CH4 ″ ″ ″ H CH3 OC2H5 CH5 ″ ″ ″ H OCH3 OCH3 N6 ″ ″ ″ H OCH3 CH3 N7 ″ ″ ″ H OCH3 Cl CH8 ″ ″ ″ H OCF2H CH3 CH9 ″ ″ ″ H OCF2H OCF2H CH10 ″ ″ ″ H OCH3 Br CH11 ″ ″ ″ H OCH3 OC2H5 CH12 ″ ″ ″ H OCH3 SCH3 CH13 ″ ″ ″ H OCH3 OC2H5 N14 ″ ″ ″ H OCH3 OC3H7 CH15 ″ ″ ″ H CH3 Cl CH16 ″ ″ ″ H Cl OC2H5 CH17 ″ ″ ″ H OC2H5 OC2H5 CH18 ″ ″ ″ H C2H5 OCH3 CH19 ″ ″ ″ H CF3 OCH3 CH20 ″ ″ ″ H OCH2CF3 CH3 CH21 ″ ″ ″ H OCH2CF3 OCH3 CH22 ″ ″ ″ H OCH2CF3 OCH2CF3 CH23 ″ ″ ″ H OCH2CF3 OCH3 N24 ″ ″ ″ H OCH3 CH(OCH3)2CH25 ″ ″ ″ CH3 OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃26 ″ ″ ″ CH3 OCH3 CH3 N27 ″ H COCH3 H OCH3 OCH3 CH 167-16928 ″ ″ ″ H OCH3 CH3 CH29 ″ ″ ″ H CH3 CH3 CH30 ″ ″ ″ H CH3 OC2H5 CH31 ″ ″ ″ H OCH3 OCH3 N32 ″ ″ ″ H OCH3 CH3 N33 ″ ″ ″ H OCH3 Cl CH34 ″ ″ ″ H OCF2H CH3 CH35 ″ ″ ″ H OCF2H OCF2H CH36 ″ ″ ″ H OCH3 Br CH37 ″ ″ ″ H OCH3 OC2H5 CH38 ″ ″ ″ H OCH3 SCH3 CH39 ″ ″ ″ H OCH3 OC2H5 N40 ″ ″ ″ H OCH3 OC3H7 CH41 ″ ″ ″ H CH3 Cl CH42 ″ ″ ″ H Cl OC2H5 CH43 ″ ″ ″ H OC2H5 OC2H5 CH44 ″ ″ ″ H C2H5 OCH3 CH45 ″ ″ ″ H CF3 OCH3 CH46 ″ ″ ″ H OCH2CF3 CH3 CH47 ″ ″ ″ H OCH2CF3 OCH3 CH48 ″ ″ ″ H OCH2CF3 OCH2CF3 CH49 ″ ″ ″ H OCH2CF3 OCH3 N50 ″ ″ ″ H OCH3 CH(OCH3)2 CH51 ″ ″ ″ CH3 OCH3 OCH3 CH52 ″ ″ ″ CH3 OCH3 CH3 N53 ″ CH3 CHO H OCH3 OCH3 CH 160-16254 ″ ″ ″ H OCH3 CH3 CH55 ″ ″ ″ H CH3 CH3 CH56 ″ ″ ″ H CH3 OC2H5 CH57 ″ ″ ″ H OCH3 OCH3 N58 ″ ″ ″ H OCH3 CH3 N59 ″ ″ ″ H OCH3 Cl CH60 ″ ″ ″ H OCF2H CH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃61 ″ ″ ″ H OCF2H OCF2H CH62 ″ ″ ″ H OCH3 Br CH63 ″ ″ ″ H OCH3 OC2H5 CH64 ″ ″ ″ H OCH3 SCH3 CH65 ″ ″ ″ H OCH3 OC2H5 N66 ″ ″ ″ H OCH3 OC3H7 CH67 ″ ″ ″ H CH3 Cl CH68 ″ ″ ″ H Cl OC2H5 CH69 ″ ″ ″ H OC2H5 OC2H5 CH70 ″ ″ ″ H C2H5 OCH3 CH71 ″ ″ ″ H CF3 OCH3 CH72 ″ ″ ″ H OCH2CF3 CH3 CH73 ″ ″ ″ H OCH2CF3 OCH3 CH74 ″ ″ ″ H OCH2CF3 OCH2CF3 CH75 ″ ″ ″ H OCH2CF3 OCH3 N76 ″ ″ ″ H OCH3 CH(OCH3)3 CH77 ″ ″ ″ CH3 OCH3 OCH3 CH78 ″ ″ ″ CH3 OCH3 CH3 N79 ″ CH3 COCH3H OCH3 OCH3 CH 166-16880 ″ ″ ″ H OCH3 CH3 CH81 ″ ″ ″ H CH3 CH3 CH82 ″ ″ ″ H CH3 OC2H5 CH83 ″ ″ ″ H OCH3 OCH3 N84 ″ ″ ″ H OCH3 CH3 N85 ″ ″ ″ H OCH3 Cl CH86 ″ ″ ″ H OCF2H CH3 CH87 ″ ″ ″ H OCF2H OCF2H CH88 ″ ″ ″ H OCH3 Br CH89 ″ ″ ″ H OCH3 OC2H5 CH90 ″ ″ ″ H OCH3 SCH3 CH91 ″ ″ ″ H OCH3 OC2H5 N92 ″ ″ ″ H OCH3 OC3H7 CH93 ″ ″ ″ H CH3 Cl CH94 ″ ″ ″ H Cl OC2H5 CH95 ″ ″ ″ H OC2H5 OC2H5 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃96 ″ ″ ″ H C2H5 OCH3 CH97 ″ ″ ″ H CF3 OCH3 CH98 ″ ″ ″ H OCH2CF3 CH3 CH99 ″ ″ ″ H OCH2CF3 OCH3 CH100 ″ ″ ″ H OCH2CF3 OCH2CF3 CH101 ″ ″ ″ H OCH2CF3 OCH3 N102 ″ ″ ″ H OCH3 CH(OCH3)2 CH103 ″ ″ ″ CH3 OCH3 OCH3 CH104 ″ ″ ″ CH3 OCH3 CH3 N105 ″ H SO2CH3 H OCH3 OCH3 CH106 ″ ″ ″ H OCH3 CH3 CH107 ″ ″ ″ H CH3 CH3 CH108 ″ ″ ″ H OCH3 OCH3 N109 ″ ″ ″ H OCH3 CH3 N110 ″ ″ ″ H OC2H5 NHCH3 N111 ″ ″ ″ CH3 OCH3 OCH3 CH112 ″ ″ ″ CH3 OCH3 CH3 N113 ″ CH3 SO2CH3 H OCH3 OCH3 CH114 ″ ″ ″ H OCH3 CH3 CH115 ″ ″ ″ H CH3 CH3 CH116 ″ ″ ″ H OCH3 OCH3 N117 ″ ″ ″ H OCH3 CH3 N118 ″ ″ ″ H OC2H5 NHCH3 N119 ″ ″ ″ CH3 OCH3 OCH3 CH120 ″ ″ ″ CH3 OCH3 CH3 N121 ″ OH CHO H OCH3 OCH3 CH122 ″ ″ ″ H OCH3 CH3 CH123 ″ ″ ″ H CH3 CH3 CH124 ″ ″ ″ H OCH3 OCH3 N125 ″ ″ ″ H OCH3 CH3 N126 ″ ″ ″ H OC2H5 NHCH3 N127 ″ ″ ″ CH3 OCH3 OCH3 CH128 ″ ″ ″ CH3 OCH3 CH3 N129 ″ OCH3 CHO H OCH3 OCH3 CH130 ″ ″ ″ H OCH3 CH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃131 ″ ″ ″ H CH3 CH3 CH132 ″ ″ ″ H OCH3 OCH3 N133 ″ ″ ″ H OCH3 CH3 N134 ″ ″ ″ H OC2H5 NHCH3 N135 ″ ″ ″ CH3 OCH3 OCH3 CH136 ″ ″ ″ CH3 OCH3 CH3 N137 ″ OH COCH3 H OCH3 OCH3 CH138 ″ ″ ″ H OCH3 CH3 CH139 ″ ″ ″ H CH3 CH3 CH140 ″ ″ ″ H OCH3 OCH3 N141 ″ ″ ″ H OCH3 CH3 N142 ″ ″ ″ H OC2H5 NHCH3 N143 ″ ″ ″ CH3 OCH3 OCH3 CH144 ″ ″ ″ CH3 OCH3 CH3 N145 ″ OCH3 COCH3 H OCH3 OCH3 CH146 ″ ″ ″ H OCH3 CH3 CH147 ″ ″ ″ H CH3 CH3 CH148 ″ ″ ″ H OCH3 OCH3 N149 ″ ″ ″ H OCH3 CH3 N150 ″ ″ ″ H OC2H5 NHCH3 N151 ″ ″ ″ CH3 OCH3 OCH3 CH152 ″ ″ ″ CH3 OCH3 CH3 N153 ″ H COC2H5 H OCH3 OCH3 CH 196154 ″ ″ ″ H OCH3 CH3 CH155 ″ ″ ″ H OCH3 OCH3 N156 ″ ″ ″ H OCH3 CH3 N157 ″ CH3 ″ H OCH3 OCH3 CH158 ″ ″ ″ H OCH3 CH3 CH159 ″ ″ ″ H OCH3 OCH3 N160 ″ ″ ″ H OCH3 CH3 N161 ″ H COCH2OCH3 H OCH3 OCH3 CH 192-195162 ″ ″ ″ H OCH3 CH3 CH163 ″ ″ ″ H OCH3 OCH3 N164 ″ ″ ″ H OCH3 CH3 N165 ″ CH3 ″ H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃166 ″ ″ ″ H OCH3 CH3 CH167 ″ ″ ″ H OCH3 OCH3 N168 ″ ″ ″ H OCH3 CH3 N169 ″ H COCO2C2H5 H OCH3 OCH3 CH 183-185170 ″ ″ ″ H OCH3 CH3 CH171 ″ ″ ″ H OCH3 OCH3 N172 ″ ″ ″ H OCH3 CH3 N173 ″ CH3 ″ H OCH3 OCH3 CH174 ″ ″ ″ H OCH3 CH3 CH175 ″ ″ ″ H OCH3 OCH3 N176 ″ ″ ″ H OCH3 CH3 N177 ″ H COCF3 H OCH3 OCH3 CH 180-182178 ″ ″ ″ H OCH3 CH3 CH179 ″ ″ ″ H OCH3 OCH3 N180 ″ ″ ″ H OCH3 CH3 N181 ″ CH3 ″ H OCH3 OCH3 CH 144-147182 ″ ″ ″ H OCH3 CH3 CH183 ″ ″ ″ H OCH3 OCH3 N184 ″ ″ ″ H OCH3 CH3 N185 ″ H COOCH3 H OCH3 OCH3 CH 178-180186 ″ ″ ″ H OCH3 CH3 CH187 ″ ″ ″ H OCH3 OCH3 N188 ″ ″ ″ H OCH3 CH3 N189 ″ CH3 ″ H OCH3 OCH3 CH190 ″ ″ ″ H OCH3 CH3 CH191 ″ ″ ″ H OCH3 OCH3 N192 ″ ″ ″ H OCH3 CH3 N193 ″ H CONHC2H5 H OCH3 OCH3 CH194 ″ ″ ″ H OCH3 CH3 CH195 ″ ″ ″ H OCH3 OCH3 N196 ″ ″ ″ H OCH3 CH3 N197 ″ CH3 ″ H OCH3 OCH3 CH198 ″ ″ ″ H OCH3 CH3 CH199 ″ ″ ″ H OCH3 OCH3 N200 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃201 ″ H CSNHC2H5 H OCH3 OCH3 CH202 ″ ″ ″ H OCH3 CH3 CH203 ″ ″ ″ H OCH3 OCH3 N204 ″ ″ ″ H OCH3 CH3 N205 ″ CH3 ″ H OCH3 OCH3 CH206 ″ ″ ″ H OCH3 CH3 CH207 ″ ″ ″ H OCH3 OCH3 N208 ″ ″ ″ H OCH3 CH3 N209 ″ H SO2NHCH3 H OCH3 OCH3 CH210 ″ ″ ″ H OCH3 CH3 CH211 ″ ″ ″ H OCH3 OCH3 N212 ″ ″ ″ H OCH3 CH3 N213 ″ CH3 ″ H OCH3 OCH3 CH214 ″ ″ ″ H OCH3 CH3 CH215 ″ ″ ″ H OCH3 OCH3 N216 ″ ″ ″ H OCH3 CH3 N217 ″ H SO2N(CH3)2 H OCH3 OCH3 CH218 ″ ″ ″ H OCH3 CH3 CH219 ″ ″ ″ H OCH3 OCH3 N220 ″ ″ ″ H OCH3 CH3 N221 ″ CH3 ″ H OCH3 OCH3 CH222 ″ ″ ″ H OCH3 CH3 CH223 ″ ″ ″ H OCH3 OCH3 N224 ″ ″ ″ H OCH3 CH3 N225 ″ -CH2CH2CH2CO- H OCH3 OCH3 CH226 ″ ″ H OCH3 CH3 CH227 ″ ″ H OCH3 OCH3 N228 ″ ″ H OCH3 CH3 N229 ″ -CH2CH2CH2SO2- H OCH3 OCH3 CH230 ″ ″ H OCH3 CH3 CH231 ″ ″ H OCH3 OCH3 N232 ″ ″ H OCH3 CH3 N233 ″ -CH2CH2CH2CH2CO- H OCH3 OCH3 CH234 ″ ″ H OCH3 CH3 CH235 ″ ″ H OCH3 OCH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃236 ″ ″ H OCH3 CH3 N237 ″ -CH2CH2CH2CH2SO2- H OCH3 OCH3 CH238 ″ ″ H OCH3 CH3 CH239 ″ ″ H OCH3 OCH3 N240 ″ ″ H OCH3 CH3 N241 ″ -CH2CH2OCH2CH2- H OCH3 OCH3 CH242 ″ ″ H OCH3 CH3 CH243 ″ ″ H OCH3 OCH3 N244 ″ ″ H OCH3 CH3 N245 ″ H COC3H7 H OCH3 OCH3 CH246 ″ ″ ″ H OCH3 CH3 CH247 ″ ″ ″ H OCH3 OCH3 N248 ″ ″ ″ H OCH3 CH3 N249 ″ CH3 ″ H OCH3 OCH3 CH250 ″ ″ ″ H OCH3 CH3 CH251 ″ ″ ″ H OCH3 OCH3 N252 ″ ″ ″ H OCH3 CH3 N253 ″ H COCH2Cl H OCH3 OCH3 CH 170-172254 ″ ″ ″ H OCH3 CH3 CH255 ″ ″ ″ H OCH3 OCH3 N256 ″ ″ ″ H OCH3 CH3 N257 ″ CH3 ″ H OCH3 OCH3 CH258 ″ ″ ″ H OCH3 CH3 CH259 ″ ″ ″ H OCH3 OCH3 N260 ″ ″ ″ H OCH3 CH3 N261 ″ H COCHCl2 H OCH3 OCH3 CH 158-160262 ″ ″ ″ H OCH3 CH3 CH263 ″ ″ ″ H OCH3 OCH3 N264 ″ ″ ″ H OCH3 CH3 N265 ″ CH3 ″ H OCH3 OCH3 CH266 ″ ″ ″ H OCH3 CH3 CH267 ″ ″ ″ H OCH3 OCH3 N268 ″ ″ ″ H OCH3 CH3 N269 ″ H COCCl3 H OCH3 OCH3 CH 194-196270 ″ ″ ″ H OCH3 CH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃271 ″ ″ ″ H OCH3 OCH3 N272 ″ ″ ″ H OCH3 CH3 N273 ″ CH3 ″ H OCH3 OCH3 CH274 ″ ″ ″ H OCH3 CH3 CH275 ″ ″ ″ H OCH3 OCH3 N276 ″ ″ ″ H OCH3 CH3 N277 ″ H COCH＝CH2 H OCH3 OCH3 CH278 ″ ″ ″ H OCH3 CH3 CH279 ″ ″ ″ H OCH3 OCH3 N280 ″ ″ ″ H OCH3 CH3 N281 ″ CH3 ″ H OCH3 OCH3 CH282 ″ ″ ″ H OCH3 CH3 CH283 ″ ″ ″ H OCH3 OCH3 N284 ″ ″ ″ H OCH3 CH3 N285 ″ H COC＝CH H OCH3 OCH3 CH286 ″ ″ ″ H OCH3 CH3 CH287 ″ ″ ″ H OCH3 OCH3 N288 ″ ″ ″ H OCH3 CH3 N289 ″ CH3 ″ H OCH3 OCH3 CH290 ″ ″ ″ H OCH3 CH3 CH291 ″ ″ ″ H OCH3 OCH3 N292 ″ ″ ″ H OCH3 CH3 N293 ″ H COC6H5 H OCH3 OCH3 CH294 ″ ″ ″ H OCH3 CH3 CH295 ″ ″ ″ H OCH3 OCH3 N296 ″ ″ ″ H OCH3 CH3 N297 ″ CH3 ″ H OCH3 OCH3 CH298 ″ ″ ″ H OCH3 CH3 CH299 ″ ″ ″ H OCH3 OCH3 N300 ″ ″ ″ H OCH3 CH3 N301 ″ SO2C6H5SO2C6H5 H OCH3 OCH3 CH302 ″ ″ ″ H OCH3 CH3 CH303 ″ ″ ″ H OCH3 OCH3 N304 ″ ″ ″ H OCH3 CH3 N305 ″ SO2CH3 SO2CH3 H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃306 ″ ″ ″ H OCH3 CH3 CH307 ″ ″ ″ H OCH3 OCH3 N308 ″ ″ ″ H OCH3 CH3 N309 ″ H COCH2Br H OCH3 OCH3 CH310 ″ ″ ″ H OCH3 CH3 N311 ″ CH3 ″ H OCH3 OCH3 CH312 ″ ″ ″ H OCH3 CH3 N313 ″ H COCH2F H OCH3 OCH3 CH314 ″ ″ ″ H OCH3 CH3 N315 ″ CH3 ″ H OCH3 OCH3 CH316 ″ ″ ″ H OCH3 CH3 N317 ″ H COCH2C＝CH H OCH3 OCH3 CH318 ″ ″ ″ H OCH3 CH3 N319 ″ CH3 ″ H OCH3 OCH3 CH320 ″ ″ ″ H OCH3 CH3 N321 ″ H COCO2CH3 H OCH3 OCH3 CH322 ″ ″ ″ H OCH3 CH3 N323 ″ CH3 ″ H OCH3 OCH3 CH324 ″ ″ ″ H OCH3 CH3 N325 ″ H CO2C2H5 H OCH3 OCH3 CH326 ″ ″ ″ H OCH3 CH3 N327 ″ CH3 ″ H OCH3 OCH3 CH328 ″ ″ ″ H OCH3 CH3 N329 ″ H COSCH3 H OCH3 OCH3 CH330 ″ ″ ″ H OCH3 CH3 N331 ″ CH3 ″ H OCH3 OCH3 CH332 ″ ″ ″ H OCH3 CH3 N333 ″ H CSOCH3 H OCH3 OCH3 CH334 ″ ″ ″ H OCH3 CH3 N335 ″ CH3 ″ H OCH3 OCH3 CH336 ″ ″ ″ H OCH3 CH3 N337 ″ H CSSCH3 H OCH3 OCH3 CH338 ″ ″ ″ H OCH3 CH3 N339 ″ CH3 ″ H OCH3 OCH3 CH340 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃341 ″ H COCH(CH3)2 H OCH3 OCH3 CH 195-196342 ″ ″ ″ H OCH3 CH3 N343 ″ CH3 ″ H OCH3 OCH3 CH344 ″ ″ ″ H OCH3 CH3 N345 ″ H COC(CH3)3 H OCH3 OCH3 CH346 ″ ″ ″ H OCH3 CH3 N347 ″ CH3 ″ H OCH3 OCH3 CH348 ″ ″ ″ H OCH3 CH3 N349 ″ H CO-环丙基 H OCH3 OCH3 CH 202-203350 ″ ″ ″ H OCH3 CH3 N351 ″ CH3 ″ H OCH3 OCH3 CH352 ″ ″ ″ H OCH3 CH3 N353 ″ H CO-环丁基 H OCH3 OCH3 CH354 ″ ″ ″ H OCH3 CH3 N355 ″ CH3 ″ H OCH3 OCH3 CH356 ″ ″ ″ H OCH3 CH3 N357 ″ H CO-环戊基 H OCH3 OCH3 CH358 ″ ″ ″ H OCH3 CH3 N359 ″ CH3 ″ H OCH3 OCH3 CH360 ″ ″ ″ H OCH3 CH3 N361 ″ H CO-环己基 H OCH3 OCH3 CH362 ″ ″ ″ H OCH3 CH3 N363 ″ CH3 ″ H OCH3 OCH3 CH364 ″ ″ ″ H OCH3 CH3 N365 ″ H CONHCH2CH2Cl H OCH3 OCH3 CH 178-182366 ″ ″ ″ H OCH3 CH3 N367 ″ CH3 ″ H OCH3 OCH3 CH368 ″ ″ ″ H OCH3 CH3 N369 ″ H CSNHCH2CH2Cl H OCH3 OCH3 CH370 ″ ″ ″ H OCH3 CH3 N371 ″ CH3 ″ H OCH3 OCH3 CH372 ″ ″ ″ H OCH3 CH3 N373 ″ H CONH-n-C4H9 H OCH3 OCH3 CH 183-184374 ″ ″ ″ H OCH3 CH3 N375 ″ CH3 ″ H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃376 ″ ″ ″ H OCH3 CH3 N377 ″ H CSNHCH3 H OCH3 OCH3 CH378 ″ ″ ″ H OCH3 CH3 N379 ″ CH3 ″ H OCH3 OCH3 CH380 ″ ″ ″ H OCH3 CH3 N381 ″ H CSNHCH2CH＝CH2 H OCH3 OCH3 CH382 ″ ″ ″ H OCH3 CH3 N383 ″ CH3 ″ H OCH3 OCH3 CH384 ″ ″ ″ H OCH3 CH3 N385 ″ CH3 CSNHCH2COCH3 H OCH3 OCH3 CH386 ″ ″ ″ H OCH3 CH3 N387 ″ CH3 CSNHCH2COC2H5 H OCH3 OCH3 CH388 ″ ″ ″ H OCH3 CH3 N389 ″ CH3 CONHCH2COCH3 H OCH3 OCH3 CH390 ″ ″ ″ H OCH3 CH3 N391 ″ CH3 CONHCH2COC2H5 H OCH3 OCH3 CH392 ″ ″ ″ H OCH3 CH3 N393 ″ -CONHCH2CO- H OCH3 OCH3 CH394 ″ ″ ″ H OCH3 CH3 N395 ″ H SO2CH2F H OCH3 OCH3 CH396 ″ ″ ″ H OCH3 CH3 N397 ″ CH3 ″ H OCH3 OCH3 CH398 ″ ″ ″ H OCH3 CH3 N399 ″ H SO2CF3 H OCH3 OCH3 CH400 ″ ″ ″ H OCH3 CH3 N401 ″ CH3 ″ H OCH3 OCH3 CH402 ″ ″ ″ H OCH3 CH3 N403 ″ H SO2C2H5 H OCH3 OCH3 CH404 ″ ″ ″ H OCH3 CH3 N405 ″ CH3 ″ H OCH3 OCH3 CH406 ″ ″ ″ H OCH3 CH3 N407 ″ H SO2-n-C3H7 H OCH3 OCH3 CH408 ″ ″ ″ H OCH3 CH3 N409 ″ CH3 ″ H OCH3 OCH3 CH410 ″ ″ ″ H OCH3 CH3 N Vb R1 R4 R5 R7 X Y Z Fp.℃411 ″ OH COC2H5 H OCH3 OCH3 CH412 ″ ″ ″ H OCH3 CH3 N413 ″ OCH3 ″ H OCH3 OCH3 CH414 ″ ″ ″ H OCH3 CH3 N415 ″ OH COCH2Cl H OCH3 OCH3 CH416 ″ ″ ″ H OCH3 CH3 N417 ″ OCH3 ″ H OCH3 OCH3 CH418 ″ ″ ″ H OCH3 CH3 N419 ″ OH COCF3 H OCH3 OCH3 CH420 ″ ″ ″ H OCH3 CH3 N421 ″ OCH3 ″ H OCH3 OCH3 CH422 ″ ″ ″ H OCH3 CH3 N423 ″ OH COCH2OCH3 H OCH3 OCH3 CH424 ″ ″ ″ H OCH3 CH3 N425 ″ OCH3 ″ H OCH3 OCH3 CH426 ″ ″ ″ H OCH3 CH3 N427 ″ OH COCO2C2H5H OCH3 OCH3 CH428 ″ ″ ″ H OCH3 CH3 N429 ″ OCH3 ″ H OCH3 OCH3 CH430 ″ ″ ″ H OCH3 CH3 N431 ″ OH COOCH3 H OCH3 OCH3 CH432 ″ ″ ″ H OCH3 CH3 N433 ″ OCH3 ″ H OCH3 OCH3 CH434 ″ ″ ″ H OCH3 CH3 N435 ″ OH 环丙基 H OCH3 OCH3 CH436 ″ ″ ″ H OCH3 CH3 N437 ″ OCH3 ″ H OCH3 OCH3 CH438 ″ ″ ″ H OCH3 CH3 N439 ″ OH COC6H5 H OCH3 OCH3 CH440 ″ ″ ″ H OCH3 CH3 N441 ″ OCH3 ″ H OCH3 OCH3 CH442 ″ ″ ″ H OCH3 CH3 N443 ″ OH COCH(CH3)2H OCH3 OCH3 CH444 ″ ″ ″ H OCH3 CH3 N445 ″ OCH3 ″ H OCH3 OCH3 CH Vb R1 R4 R5 R7 X Y Z Fp.℃446 ″ ″ ″ H OCH3 CH3 N447 ″ OH COCH＝CH2 H OCH3 OCH3 CH448 ″ ″ ″ H OCH3 CH3 N449 ″ OCH3 ″ H OCH3 OCH3 CH450 ″ ″ ″ H OCH3 CH3 N451 ″ OH COC＝CH H OCH3 OCH3 CH452 ″ ″ ″ H OCH3 CH3 N453 ″ OCH3 ″ H OCH3 OCH3 CH454 ″ ″ ″ H OCH3 CH3 N455 ″ OH SO2CH3 H OCH3 OCH3 CH456 ″ ″ ″ H OCH3 CH3 N457 ″ OCH3 ″ H OCH3 OCH3 CH458 ″ ″ ″ H OCH3 CH3 N459 ″ OH SO2NHCH3 H OCH3 OCH3 CH460 ″ ″ ″ H OCH3 CH3 N461 ″ OCH3 ″ H OCH3 OCH3 CH462 ″ ″ ″ H OCH3 CH3 N463 ″ OH SO2N(CH3)2H OCH3 OCH3 CH464 ″ ″ ″ H OCH3 CH3 N465 ″ OCH3 ″ H OCH3 OCH3 CH466 ″ ″ ″ H OCH3 CH3 N467 ″ C2H5CHO H OCH3 OCH3 CH468 ″ ″ ″ H OCH3 CH3 N469 ″ ″ COCH3 H OCH3 OCH3 CH470 ″ ″ ″ H OCH3 CH3 N471 ″ ″ 环丙基 H OCH3 OCH3 CH472 ″ ″ ″ H OCH3 CH3 N473 ″ ″ COCH2Cl H OCH3 OCH3 CH474 ″ ″ ″ H OCH3 CH3 N475 ″ ″ COCF3 H OCH3 OCH3 CH476 ″ ″ ″ H OCH3 CH3 N477 ″ ″ COOCH3 H OCH3 OCH3 CH478 ″ ″ ″ H OCH3 CH3 N479 ″ ″ COC6H5 H OCH3 OCH3 CH480 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃481 ″ ″ CONHC2H5 H OCH3 OCH3 CH482 ″ ″ ″ H OCH3 CH3 N483 ″ ″ CSNHC2H5 H OCH3 OCH3 CH484 ″ ″ ″ H OCH3 CH3 N485 ″ ″ SO2CH3 H OCH3 OCH3 CH486 ″ ″ ″ H OCH3 CH3 N487 ″ ″ SO2NHCH3 H OCH3 OCH3 CH488 ″ ″ ″ H OCH3 CH3 N489 ″ ″ SO2N(CH3)2 H OCH3 OCH3 CH490 ″ ″ ″ H OCH3 CH3 N491 ″ ″ SO2C6H5 H OCH3 OCH3 CH492 ″ ″ ″ H OCH3 CH3 N493 CO2C2H5 H CHO H OCH3 OCH3 CH494 ″ ″ ″ H OCH3 CH3 N495 ″ ″ COCH3 H OCH3 OCH3 CH496 ″ ″ ″ H OCH3 CH3 N497 ″ ″ SO2CH3 H OCH3 OCH3 CH498 ″ ″ ″ H OCH3 CH3 N499 ″ CH3 CHO H OCH3 OCH3 CH500 ″ ″ ″ H OCH3 CH3 N501 ″ ″ COCH3 H OCH3 OCH3 CH502 ″ ″ ″ H OCH3 CH3 N503 ″ ″ SO2CH3 H OCH3 OCH3 CH504 ″ ″ ″ H OCH3 CH3 N505 ″ C2H5CHO H OCH3 OCH3 CH506 ″ ″ ″ H OCH3 CH3 N507 ″ ″ COCH3 H OCH3 OCH3 CH508 ″ ″ ″ H OCH3 CH3 N509 ″ ″ SO2CH3 H OCH3 OCH3 CH510 ″ ″ ″ H OCH3 CH3 N511 ″ OH CHO H OCH3 OCH3 CH512 ″ ″ ″ H OCH3 CH3 N513 ″ ″ COCH3 H OCH3 OCH3 CH514 ″ ″ ″ H OCH3 CH3 N515 ″ ″ SO2CH3 H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃516 ″ ″ ″ H OCH3 CH3 N517 ″ OCH3 CHO H OCH3 OCH3 CH518 ″ ″ ″ H OCH3 CH3 N519 ″ ″ COCH3 H OCH3 OCH3 CH520 ″ ″ ″ H OCH3 CH3 N521 CO2-n-Bu H CHO H ″ OMe CH522 CONMe2 Me ″ H ″ Me N523 CONHMe H ″ H ″ OMe CH524 COSMe Me CO-Me H ″ Me N525 CO2Me n-Bu CHO H ″ OMe CH526 ″ n-Bu ″ H ″ Me N527 ″ H ″ H OCH2CF3NMe2 ″528 ″ Me ″ H ″ ″ ″529 ″ H CO-Me H ″ ″ ″530 ″ Me ″ H ″ ″ ″531 ″ ″ SO2CH3 H OCH3 OCH3 CH532 ″ ″ ″ H OCH3 CH3 N533 ″
H OCH3 OCH3 CH534 ″ ″ H OCH3 CH3 N
表3
Vb R1 R4 R5 R7 X Y Z Fp.℃1 CO2CH3 H CHO H OCH3 OCH3 CH2 ″ ″ ″ H OCH3 CH3 CH3 ″ ″ ″ H CH3 CH3 CH4 ″ ″ ″ H CH3 OC2H5 CH5 ″ ″ ″ H OCH3 OCH3 N6 ″ ″ ″ H OCH3 CH3 N7 ″ ″ ″ H OCH3 Cl CH8 ″ ″ ″ H OCF2H CH3 CH9 ″ ″ ″ H OCF2H OCF2H CH10 ″ ″ ″ H OCH3 Br CH11 ″ ″ ″ H OCH3 OC2H5 CH12 ″ ″ ″ H OCH3 SCH3 CH13 ″ ″ ″ H OCH3 OC2H5 N14 ″ ″ ″ H OCH3 OC3H7 CH15 ″ ″ ″ H CH3 Cl CH16 ″ ″ ″ H Cl OC2H5 CH17 ″ ″ ″ H OC2H5 OC2H5 CH18 ″ ″ ″ H C2H5 OCH3 CH19 ″ ″ ″ H CF3 OCH3 CH20 ″ ″ ″ H OCH2CF3 CH3 CH21 ″ ″ ″ H OCH2CF3 OCH3 CH22 ″ ″ ″ H OCH2CF3 OCH2CF3 CH23 ″ ″ ″ H OCH2CF3 OCH3 N24 ″ ″ ″ H OCH3 CH(OCH3)2CH Vb. R1 R4 R5 R7 X Y Z Fp.℃25 ″ ″ ″ CH3 OCH3 OCH3 CH26 ″ ″ ″ CH3 OCH3 CH3 N27 ″ H COCH3H OCH3 OCH3 CH 198-20028 ″ ″ ″ H OCH3 CH3 CH29 ″ ″ ″ H CH3 CH3 CH30 ″ ″ ″ H CH3 OC2H5 CH31 ″ ″ ″ H OCH3 OCH3 N32 ″ ″ ″ H OCH3 CH3 N33 ″ ″ ″ H OCH3 Cl CH34 ″ ″ ″ H OCF2H CH3 CH35 ″ ″ ″ H OCF2H OCF2H CH36 ″ ″ ″ H OCH3 Br CH37 ″ ″ ″ H OCH3 OC2H5 CH38 ″ ″ ″ H OCH3 SCH3 CH39 ″ ″ ″ H OCH3 OC2H5 N40 ″ ″ ″ H OCH3 OC3H7 CH41 ″ ″ ″ H CH3 Cl CH42 ″ ″ ″ H Cl OC2H5 CH43 ″ ″ ″ H OC2H5 OC2H5 CH44 ″ ″ ″ H C2H5 OCH3 CH45 ″ ″ ″ H CF3 OCH3 CH46 ″ ″ ″ H OCH2CF3 CH3 CH47 ″ ″ ″ H OCH2CF3 OCH3 CH48 ″ ″ ″ H OCH2CF3 OCH2CF3 CH49 ″ ″ ″ H OCH2CF3 OCH3 N50 ″ ″ ″ H OCH3 CH(OCH3)2 CH51 ″ ″ ″ CH3 OCH3 OCH3 CH52 ″ ″ ″ CH3 OCH3 CH3 N53 ″ CH3 CHO H OCH3 OCH3 CH54 ″ ″ ″ H OCH3 CH3 CH55 ″ ″ ″ H CH3 CH3 CH56 ″ ″ ″ H CH3 OC2H5 CH57 ″ ″ ″ H OCH3 OCH3 N58 ″ ″ ″ H OCH3 CH3 N59 ″ ″ ″ H OCH3 Cl CH Vb. R1 R4 R5 R7 X Y Z Fp.℃60 ″ ″ ″ H OCF2H CH3 CH61 ″ ″ ″ H OCF2H OCF2H CH62 ″ ″ ″ H OCH3 Br CH63 ″ ″ ″ H OCH3 OC2H5 CH64 ″ ″ ″ H OCH3 SCH3 CH65 ″ ″ ″ H OCH3 OC2H5 N66 ″ ″ ″ H OCH3 OC3H7 CH67 ″ ″ ″ H CH3 Cl CH68 ″ ″ ″ H Cl OC2H5 CH69 ″ ″ ″ H OC2H5 OC2H5 CH70 ″ ″ ″ H C2H5 OCH3 CH71 ″ ″ ″ H CF3 OCH3 CH72 ″ ″ ″ H OCH2CF3 CH3 CH73 ″ ″ ″ H OCH2CF3 OCH3 CH74 ″ ″ ″ H OCH2CF3 OCH2CF3 CH75 ″ ″ ″ H OCH2CF3 OCH3 N76 ″ ″ ″ H OCH3 CH(OCH3)2 CH77 ″ ″ ″ CH3 OCH3 OCH3 CH78 ″ ″ ″ CH3 OCH3 CH3 N79 ″ CH3 COCH3H OCH3 OCH3 CH80 ″ ″ ″ H OCH3 CH3 CH81 ″ ″ ″ H CH3 CH3 CH82 ″ ″ ″ H CH3 OC2H5 CH83 ″ ″ ″ H OCH3 OCH3 N84 ″ ″ ″ H OCH3 CH3 N85 ″ ″ ″ H OCH3 Cl CH86 ″ ″ ″ H OCF2H CH3 CH87 ″ ″ ″ H OCF2H OCF2H CH88 ″ ″ ″ H OCH3 Br CH89 ″ ″ ″ H OCH3 OC2H5 CH90 ″ ″ ″ H OCH3 SCH3 CH91 ″ ″ ″ H OCH3 OC2H5 N92 ″ ″ ″ H OCH3 OC3H7 CH93 ″ ″ ″ H CH3 Cl CH94 ″ ″ ″ H Cl OC2H5 CH Vb R1 R4 R5 R7 X Y Z Fp.℃95 ″ ″ ″ H OC2H5 OC2H5 CH96 ″ ″ ″ H C2H5 OCH3 CH97 ″ ″ ″ H CF3 OCH3 CH98 ″ ″ ″ H OCH2CF3 CH3 CH99 ″ ″ ″ H OCH2CF3 OCH3 CH100 ″ ″ ″ H OCH2CF3 OCH2CF3 CH101 ″ ″ ″ H OCH2CF3 OCH3 N102 ″ ″ ″ H OCH3 CH(OCH3)2 CH103 ″ ″ ″ CH3 OCH3 OCH3 CH104 ″ ″ ″ CH3 OCH3 CH3 N105 ″ H SO2CH3 H OCH3 OCH3 CH106 ″ ″ ″ H OCH3 CH3 CH107 ″ ″ ″ H CH3 CH3 CH108 ″ ″ ″ H OCH3 OCH3 N109 ″ ″ ″ H OCH3 CH3 N110 ″ ″ ″ H OC2H5 NHCH3 N111 ″ ″ ″ CH3 OCH3 OCH3 CH112 ″ ″ ″ CH3 OCH3 CH3 N113 ″ CH3 SO2CH3H OCH3 OCH3 CH114 ″ ″ ″ H OCH3 CH3 CH115 ″ ″ ″ H CH3 CH3 CH116 ″ ″ ″ H OCH3 OCH3 N117 ″ ″ ″ H OCH3 CH3 N118 ″ ″ ″ H OC2H5 NHCH3 N119 ″ ″ ″ CH3 OCH3 OCH3 CH120 ″ ″ ″ CH3 OCH3 CH3 N121 ″ OH CHO H OCH3 OCH3 CH122 ″ ″ ″ H OCH3 CH3 CH123 ″ ″ ″ H CH3 CH3 CH124 ″ ″ ″ H OCH3 OCH3 N125 ″ ″ ″ H OCH3 CH3 N126 ″ ″ ″ H OC2H5 NHCH3 N127 ″ ″ ″ CH3 OCH3 OCH3 CH128 ″ ″ ″ CH3 OCH3 CH3 N129 ″ OCH3 CHO H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃130 ″ ″ ″ H OCH3 CH3 CH131 ″ ″ ″ H CH3 CH3 CH132 ″ ″ ″ H OCH3 OCH3 N133 ″ ″ ″ H OCH3 CH3 N134 ″ ″ ″ H OC2H5 NHCH3 N135 ″ ″ ″ CH3 OCH3 OCH3 CH136 ″ ″ ″ CH3 OCH3 CH3 N137 ″ OH COCH3 H OCH3 OCH3 CH138 ″ ″ ″ H OCH3 CH3 CH139 ″ ″ ″ H CH3 CH3 CH140 ″ ″ ″ H OCH3 OCH3 N141 ″ ″ ″ H OCH3 CH3 N142 ″ ″ ″ H OC2H5 NHCH3 N143 ″ ″ ″ CH3 OCH3 OCH3 CH144 ″ ″ ″ CH3 OCH3 CH3 N145 ″ OCH3 COCH3 H OCH3 OCH3 CH146 ″ ″ ″ H OCH3 CH3 CH147 ″ ″ ″ H CH3 CH3 CH148 ″ ″ ″ H OCH3 OCH3 N149 ″ ″ ″ H OCH3 CH3 N150 ″ ″ ″ H OC2H5 NHCH3 N151 ″ ″ ″ CH3 OCH3 OCH3 CH152 ″ ″ ″ CH3 OCH3 CH3 N153 ″ H COC2H5 H OCH3 OCH3 CH154 ″ ″ ″ H OCH3 CH3 CH155 ″ ″ ″ H OCH3 OCH3 N156 ″ ″ ″ H OCH3 CH3 N157 ″ CH3 ″ H OCH3 OCH3 CH158 ″ ″ ″ H OCH3 CH3 CH159 ″ ″ ″ H OCH3 OCH3 N160 ″ ″ ″ H OCH3 CH3 N161 ″ H COCH2OCH3H OCH3 OCH3 CH162 ″ ″ ″ H OCH3 CH3 CH163 ″ ″ ″ H OCH3 OCH3 N164 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃165 ″ CH3 ″ H OCH3 OCH3 CH166 ″ ″ ″ H OCH3 CH3 CH167 ″ ″ ″ H OCH3 OCH3 N168 ″ ″ ″ H OCH3 CH3 N169 ″ H COCO2C2H5H OCH3 OCH3 CH170 ″ ″ ″ H OCH3 CH3 CH171 ″ ″ ″ H OCH3 OCH3 N172 ″ ″ ″ H OCH3 CH3 N173 ″ CH3 ″ H OCH3 OCH3 CH174 ″ ″ ″ H OCH3 CH3 CH175 ″ ″ ″ H OCH3 OCH3 N176 ″ ″ ″ H OCH3 CH3 N177 ″ H COCF3 H OCH3 OCH3 CH178 ″ ″ ″ H OCH3 CH3 CH179 ″ ″ ″ H OCH3 OCH3 N180 ″ ″ ″ H OCH3 CH3 N181 ″ CH3 ″ H OCH3 OCH3 CH182 ″ ″ ″ H OCH3 CH3 CH183 ″ ″ ″ H OCH3 OCH3 N184 ″ ″ ″ H OCH3 CH3 N185 ″ H COOCH3 H OCH3 OCH3 CH186 ″ ″ ″ H OCH3 CH3 CH187 ″ ″ ″ H OCH3 OCH3 N188 ″ ″ ″ H OCH3 CH3 N189 ″ CH3 ″ H OCH3 OCH3 CH190 ″ ″ ″ H OCH3 CH3 CH191 ″ ″ ″ H OCH3 OCH3 N192 ″ ″ ″ H OCH3 CH3 N193 ″ H CONHC2H5 H OCH3 OCH3 CH194 ″ ″ ″ H OCH3 CH3 CH195 ″ ″ ″ H OCH3 OCH3 N196 ″ ″ ″ H OCH3 CH3 N197 ″ CH3 ″ H OCH3 OCH3 CH198 ″ ″ ″ H OCH3 CH3 CH199 ″ ″ ″ H OCH3 OCH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃200 ″ ″ ″ H OCH3 CH3 N201 ″ H CSNHC2H5 H OCH3 OCH3 CH202 ″ ″ ″ H OCH3 CH3 CH203 ″ ″ ″ H OCH3 OCH3 N204 ″ ″ ″ H OCH3 CH3 N205 ″ CH3 ″ H OCH3 OCH3 CH206 ″ ″ ″ H OCH3 CH3 CH207 ″ ″ ″ H OCH3 OCH3 N208 ″ ″ ″ H OCH3 CH3 N209 ″ H SO2NHCH3 H OCH3 OCH3 CH210 ″ ″ ″ H OCH3 CH3 CH211 ″ ″ ″ H OCH3 OCH3 N212 ″ ″ ″ H OCH3 CH3 N213 ″ CH3 ″ H OCH3 OCH3 CH214 ″ ″ ″ H OCH3 CH3 CH215 ″ ″ ″ H OCH3 OCH3 N216 ″ ″ ″ H OCH3 CH3 N217 ″ H SO2N(CH3)2H OCH3 OCH3 CH218 ″ ″ ″ H OCH3 CH3 CH219 ″ ″ ″ H OCH3 OCH3 N220 ″ ″ ″ H OCH3 CH3 N221 ″ CH3 ″ H OCH3 OCH3 CH222 ″ ″ ″ H OCH3 CH3 CH223 ″ ″ ″ H OCH3 OCH3 N224 ″ ″ ″ H OCH3 CH3 N225 ″ -CH2CH2CH2CO- H OCH3 OCH3 CH226 ″ ″ H OCH3 CH3 CH227 ″ ″ H OCH3 OCH3 N228 ″ ″ H OCH3 CH3 N229 ″ -CH2CH2CH2SO2- H OCH3 OCH3 CH230 ″ ″ H OCH3 CH3 CH231 ″ ″ H OCH3 OCH3 N232 ″ ″ H OCH3 CH3 N233 ″ -CH2CH2CH2CH2CO- H OCH3 OCH3 CH234 ″ ″ H OCH3 CH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃235 ″ ″ H OCH3 OCH3 N236 ″ ″ H OCH3 CH3 N237 ″ -CH2CH2CH2CH2SO2-H OCH3 OCH3 CH238 ″ ″ H OCH3 CH3 CH239 ″ ″ H OCH3 OCH3 N240 ″ ″ H OCH3 CH3 N241 ″ -CH2CH2OCH2CH2- H OCH3 OCH3 CH242 ″ ″ H OCH3 CH3 CH243 ″ ″ H OCH3 OCH3 N244 ″ ″ H OCH3 CH3 N245 ″ H COC3H7 H OCH3 OCH3 CH246 ″ ″ ″ H OCH3 CH3 CH247 ″ ″ ″ H OCH3 OCH3 N248 ″ ″ ″ H OCH3 CH3 N249 ″ CH3 ″ H OCH3 OCH3 CH250 ″ ″ ″ H OCH3 CH3 CH251 ″ ″ ″ H OCH3 OCH3 N252 ″ ″ ″ H OCH3 CH3 N253 ″ H COCH2Cl H OCH3 OCH3 CH254 ″ ″ ″ H OCH3 CH3 CH255 ″ ″ ″ H OCH3 OCH3 N256 ″ ″ ″ H OCH3 CH3 N257 ″ CH3 ″ H OCH3 OCH3 CH258 ″ ″ ″ H OCH3 CH3 CH259 ″ ″ ″ H OCH3 OCH3 N260 ″ ″ ″ H OCH3 CH3 N261 ″ H COCHCl2 H OCH3 OCH3 CH262 ″ ″ ″ H OCH3 CH3 CH263 ″ ″ ″ H OCH3 OCH3 N264 ″ ″ ″ H OCH3 CH3 N265 ″ CH3 ″ H OCH3 OCH3 CH266 ″ ″ ″ H OCH3 CH3 CH267 ″ ″ ″ H OCH3 OCH3 N268 ″ ″ ″ H OCH3 CH3 N269 ″ H COCCl3 H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃270 ″ ″ ″ H OCH3 CH3 CH271 ″ ″ ″ H OCH3 OCH3 N272 ″ ″ ″ H OCH3 CH3 N273 ″ CH3 ″ H OCH3 OCH3 CH274 ″ ″ ″ H OCH3 CH3 CH275 ″ ″ ″ H OCH3 OCH3 N276 ″ ″ ″ H OCH3 CH3 N277 ″ H COCH＝CH2 H OCH3 OCH3 CH278 ″ ″ ″ H OCH3 CH3 CH279 ″ ″ ″ H OCH3 OCH3 N280 ″ ″ ″ H OCH3 CH3 N281 ″ CH3 ″ H OCH3 OCH3 CH282 ″ ″ ″ H OCH3 CH3 CH283 ″ ″ ″ H OCH3 OCH3 N284 ″ ″ ″ H OCH3 CH3 N285 ″ H COC＝CH H OCH3 OCH3 CH286 ″ ″ ″ H OCH3 CH3 CH287 ″ ″ ″ H OCH3 OCH3 N288 ″ ″ ″ H OCH3 CH3 N289 ″ CH3 ″ H OCH3 OCH3 CH290 ″ ″ ″ H OCH3 CH3 CH291 ″ ″ ″ H OCH3 OCH3 N292 ″ ″ ″ H OCH3 CH3 N293 ″ H COC6H5 H OCH3 OCH3 CH294 ″ ″ ″ H OCH3 CH3 CH295 ″ ″ ″ H OCH3 OCH3 N296 ″ ″ ″ H OCH3 CH3 N297 ″ CH3 ″ H OCH3 OCH3 CH298 ″ ″ ″ H OCH3 CH3 CH299 ″ ″ ″ H OCH3 OCH3 N300 ″ ″ ″ H OCH3 CH3 N301 ″ SO2C6H5 SO2C6H5H OCH3 OCH3 CH302 ″ ″ ″ H OCH3 CH3 CH303 ″ ″ ″ H OCH3 OCH3 N304 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃305 ″ SO2CH3 SO2CH3 H OCH3 OCH3 CH306 ″ ″ ″ H OCH3 CH3 CH307 ″ ″ ″ H OCH3 OCH3 N308 ″ ″ ″ H OCH3 CH3 N309 ″ H COCH2Br H OCH3 OCH3 CH310 ″ ″ ″ H OCH3 CH3 N311 ″ CH3 ″ H OCH3 OCH3 CH312 ″ ″ ″ H OCH3 CH3 N313 ″ H COCH2F H OCH3 OCH3 CH314 ″ ″ ″ H OCH3 CH3 N315 ″ CH3 ″ H OCH3 OCH3 CH316 ″ ″ ″ H OCH3 CH3 N317 ″ H COCH2C＝CH H OCH3 OCH3 CH318 ″ ″ ″ H OCH3 CH3 N319 ″ CH3 ″ H OCH3 OCH3 CH320 ″ ″ ″ H OCH3 CH3 N321 ″ H COCO2CH3 H OCH3 OCH3 CH322 ″ ″ ″ H OCH3 CH3 N323 ″ CH3 ″ H OCH3 OCH3 CH324 ″ ″ ″ H OCH3 CH3 N325 ″ H CO2C2H5 H OCH3 OCH3 CH326 ″ ″ ″ H OCH3 CH3 N327 ″ CH3 ″ H OCH3 OCH3 CH328 ″ ″ ″ H OCH3 CH3 N329 ″ H COSCH3 H OCH3 OCH3 CH330 ″ ″ ″ H OCH3 CH3 N331 ″ CH3 ″ H OCH3 OCH3 CH332 ″ ″ ″ H OCH3 CH3 N333 ″ H CSOCH3 H OCH3 OCH3 CH334 ″ ″ ″ H OCH3 CH3 N335 ″ CH3 ″ H OCH3 OCH3 CH336 ″ ″ ″ H OCH3 CH3 N337 ″ H CSSCH3 H OCH3 OCH3 CH338 ″ ″ ″ H OCH3 CH3 N339 ″ CH3 ″ H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃340 ″ ″ ″ H OCH3 CH3 N341 ″ H COCH(CH3)2 H OCH3 OCH3 CH342 ″ ″ ″ H OCH3 CH3 N343 ″ CH3 ″ H OCH3 OCH3 CH344 ″ ″ ″ H OCH3 CH3 N345 ″ H COC(CH3)3 H OCH3 OCH3 CH346 ″ ″ ″ H OCH3 CH3 N347 ″ CH3 ″ H OCH3 OCH3 CH348 ″ ″ ″ H OCH3 CH3 N349 ″ H CO-环丙基 H OCH3 OCH3 CH350 ″ ″ ″ H OCH3 CH3 N351 ″ CH3 ″ H OCH3 OCH3 CH352 ″ ″ ″ H OCH3 CH3 N353 ″ H CO-环丁基 H OCH3 OCH3 CH354 ″ ″ ″ H OCH3 CH3 N355 ″ CH3 ″ H OCH3 OCH3 CH356 ″ ″ ″ H OCH3 CH3 N357 ″ H CO-环戊基 H OCH3 OCH3 CH358 ″ ″ ″ H OCH3 CH3 N359 ″ CH3 ″ H OCH3 OCH3 CH360 ″ ″ ″ H OCH3 CH3 N361 ″ H CO-环己基 H OCH3 OCH3 CH362 ″ ″ ″ H OCH3 CH3 N363 ″ CH3 ″ H OCH3 OCH3 CH364 ″ ″ ″ H OCH3 CH3 N365 ″ H CONHCH2CH2ClH OCH3 OCH3 CH366 ″ ″ ″ H OCH3 CH3 N367 ″ CH3 ″ H OCH3 OCH3 CH36B ″ ″ ″ H OCH3 CH3 N369 ″ H CSNHCH2CH2ClH OCH3 OCH3 CH370 ″ ″ ″ H OCH3 CH3 N371 ″ CH3 ″ H OCH3 OCH3 CH372 ″ ″ ″ H OCH3 CH3 N373 ″ H CONH-n-C4H9 H OCH3 OCH3 CH374 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃375 ″ CH3 ″ H OCH3 OCH3 CH376 ″ ″ ″ H OCH3 CH3 N377 ″ H CSNHCH3 H OCH3 OCH3 CH378 ″ ″ ″ H OCH3 CH3 N379 ″ CH3 ″ H OCH3 OCH3 CH380 ″ ″ ″ H OCH3 CH3 N381 ″ H CSNHCH2CH＝CH2H OCH3 OCH3 CH382 ″ ″ ″ H OCH3 CH3 N383 ″ CH3 ″ H OCH3 OCH3 CH384 ″ ″ ″ H OCH3 CH3 N385 ″ CH3 CSNHCH2COCH3 H OCH3 OCH3 CH386 ″ ″ ″ H OCH3 CH3 N387 ″ CH3 CSNHCH2COC2H5H OCH3 OCH3 CH388 ″ ″ ″ H OCH3 CH3 N389 ″ CH3 CONHCH2COCH3 H OCH3 OCH3 CH390 ″ ″ ″ H OCH3 CH3 N391 ″ CH3 CONHCH2COC2H5H OCH3 OCH3 CH392 ″ ″ ″ H OCH3 CH3 N393 ″ -CONHCH2CO- H OCH3 OCH3 CH394 ″ ″ H OCH3 CH3 N395 ″ H SO2CH2F H OCH3 OCH3 CH396 ″ ″ ″ H OCH3 CH3 N397 ″ CH3 ″ H OCH3 OCH3 CH398 ″ ″ ″ H OCH3 CH3 N399 ″ H SO2CF3 H OCH3 OCH3 CH400 ″ ″ ″ H OCH3 CH3 N401 ″ CH3 ″ H OCH3 OCH3 CH402 ″ ″ ″ H OCH3 CH3 N403 ″ H SO2C2H5 H OCH3 OCH3 CH404 ″ ″ ″ H OCH3 CH3 N405 ″ CH3 ″ H OCH3 OCH3 CH406 ″ ″ ″ H OCH3 CH3 N407 ″ H SO2-n-C3H7 H OCH3 OCH3 CH408 ″ ″ ″ H OCH3 CH3 N409 ″ CH3 ″ H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃410 ″ ″ ″ H OCH3 CH3 N411 ″ OH COC2H5 H OCH3 OCH3 CH412 ″ ″ ″ H OCH3 CH3 N413 ″ OCH3 ″ H OCH3 OCH3 CH414 ″ ″ ″ H OCH3 CH3 N415 ″ OH COCH2Cl H OCH3 OCH3 CH416 ″ ″ ″ H OCH3 CH3 N417 ″ OCH3 ″ H OCH3 OCH3 CH418 ″ ″ ″ H OCH3 CH3 N419 ″ OH COCF3 H OCH3 OCH3 CH420 ″ ″ ″ H OCH3 CH3 N421 ″ OCH3 ″ H OCH3 OCH3 CH422 ″ ″ ″ H OCH3 CH3 N423 ″ OH COCH2OCH3 H OCH3 OCH3 CH424 ″ ″ ″ H OCH3 CH3 N425 ″ OCH3 ″ H OCH3 OCH3 CH426 ″ ″ ″ H OCH3 CH3 N427 ″ OH COCO2C2H5 H OCH3 OCH3 CH428 ″ ″ ″ H OCH3 CH3 N429 ″ OCH3 ″ H OCH3 OCH3 CH430 ″ ″ ″ H OCH3 CH3 N431 ″ OH COOCH3 H OCH3 OCH3 CH432 ″ ″ ″ H OCH3 CH3 N433 ″ OCH3 ″ H OCH3 OCH3 CH434 ″ ″ ″ H OCH3 CH3 N435 ″ OH 环丙基 H OCH3 OCH3 CH436 ″ ″ ″ H OCH3 CH3 N437 ″ OCH3 ″ H OCH3 OCH3 CH438 ″ ″ ″ H OCH3 CH3 N439 ″ OH COC6H5 H OCH3 OCH3 CH440 ″ ″ ″ H OCH3 CH3 N441 ″ OCH3 ″ H OCH3 OCH3 CH442 ″ ″ ″ H OCH3 CH3 N443 ″ OH COCH(CH3)2 H OCH3 OCH3 CH444 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃445 ″ OCH3 ″ H OCH3 OCH3 CH446 ″ ″ ″ H OCH3 CH3 N447 ″ OH COCH＝CH2 H OCH3 OCH3 CH448 ″ ″ ″ H OCH3 CH3 N449 ″ OCH3 ″ H OCH3 OCH3 CH450 ″ ″ ″ H OCH3 CH3 N451 ″ OH COC＝CH H OCH3 OCH3 CH452 ″ ″ ″ H OCH3 CH3 N453 ″ OCH3 ″ H OCH3 OCH3 CH454 ″ ″ H OCH3 CH3 N455 ″ OH SO2CH3 H OCH3 OCH3 CH456 ″ ″ ″ H OCH3 CH3 N457 ″ OCH3 ″ H OCH3 OCH3 CH458 ″ ″ ″ H OCH3 CH3 N459 ″ OH SO2NHCH3 H OCH3 OCH3 CH460 ″ ″ ″ H OCH3 CH3 N461 ″ OCH3 ″ H OCH3 OCH3 CH462 ″ ″ ″ H OCH3 CH3 N463 ″ OH SO3N(CH3)2H OCH3 OCH3 CH464 ″ ″ ″ H OCH3 CH3 N465 ″ OCH3 ″ H OCH3 OCH3 CH466 ″ ″ ″ H OCH3 CH3 N467 ″ C2H5CHO H OCH3 OCH3 CH468 ″ ″ ″ H OCH3 CH3 N469 ″ ″ COCH3 H OCH3 OCH3 CH470 ″ ″ ″ H OCH3 CH3 N471 ″ ″ 环丙基 H OCH3 OCH3 CH472 ″ ″ ″ H OCH3 CH3 N473 ″ ″ COCH2Cl H OCH3 OCH3 CH474 ″ ″ ″ H OCH3 CH3 N475 ″ ″ COCF3 H OCH3 OCH3 CH476 ″ ″ ″ H OCH3 CH3 N477 ″ ″ COOCH3 H OCH3 OCH3 CH478 ″ ″ ″ H OCH3 CH3 N479 ″ ″ COC6H5 H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃480 ″ ″ ″ H OCH3 CH3 N481 ″ ″ CONHC2H5 H OCH3 OCH3 CH482 ″ ″ ″ H OCH3 CH3 N483 ″ ″ CSNHC2H5 H OCH3 OCH3 CH484 ″ ″ ″ H OCH3 CH3 N485 ″ ″ SO2CH3 H OCH3 OCH3 CH486 ″ ″ ″ H OCH3 CH3 N487 ″ ″ SO2NHCH3 H OCH3 OCH3 CH488 ″ ″ ″ H OCH3 CH3 N489 ″ ″ SO2N(CH3)2H OCH3 OCH3 CH490 ″ ″ ″ H OCH3 CH3 N491 ″ ″ SO2C6H5 H OCH3 OCH3 CH492 ″ ″ ″ H OCH3 CH3 N493 CO2C2H5H CHO H OCH3 OCH3 CH494 ″ ″ ″ H OCH3 CH3 N495 ″ ″ COCH3 H OCH3 OCH3 CH496 ″ ″ ″ H OCH3 CH3 N497 ″ ″ SO2CH3 H OCH3 OCH3 CH498 ″ ″ ″ H OCH3 CH3 N499 ″ CH3 CHO H OCH3 OCH3 CH500 ″ ″ ″ H OCH3 CH3 N501 ″ ″ COCH3 H OCH3 OCH3 CH502 ″ ″ ″ H OCH3 CH3 N503 ″ ″ SO2CH3 H OCH3 OCH3 CH504 ″ ″ ″ H OCH3 CH3 N505 ″ C2H5 CHO H OCH3 OCH3 CH506 ″ ″ ″ H OCH3 CH3 N507 ″ ″ COCH3 H OCH3 OCH3 CH508 ″ ″ ″ H OCH3 CH3 N509 ″ ″ SO2CH3 H OCH3 OCH3 CH510 ″ ″ ″ H OCH3 CH3 N511 ″ OH CHO H OCH3 OCH3 CH512 ″ ″ ″ H OCH3 CH3 N513 ″ ″ COCH3 H OCH3 OCH3 CH514 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃515 ″ ″ SO2CH3 H OCH3 OCH3 CH516 ″ ″ ″ H OCH3 CH3 N517 ″ OCH3 CHO H OCH3 OCH3 CH518 ″ ″ ″ H OCH3 CH3 N519 ″ ″ COCH3 H OCH3 OCH3 CH520 ″ ″ ″ H OCH3 CH3 N521 COO-n-Bu H CHO H ″ OMe CH522 CONMe2 Me ″ H ″ Me N523 CONHMe H ″ H ″ OMe CH524 COSMe Me CO-Me H ″ Me N525 COOMe n-Bu CHO H ″ OMe CH526 ″ ″ ″ H ″ Me N527 ″ H ″ H OCH2CF3 NMe2 N528 ″ Me ″ H ″ ″ N529 ″ H CO-Me H ″ ″ N530 ″ Me ″ H ″ ″ N531 ″ ″ SO2CH3 H OCH3 OCH3 CH532 ″ ″ ″ H OCH3 CH3 N533 ″
H OCH3 OCH3 CH534 ″ ″ H OCH3 CH3 N535 CO2CH3 H COCH3 H OCH3 OCH3 CH Na-Salz270
表4Vb. R1 R4 R5 R7 X Y Z Fp.℃1 CO2CH3H CHO H OCH3 OCH3 CH2 ″ ″ ″ H OCH3 CH3 CH3 ″ ″ ″ H CH3 CH3 CH4 ″ ″ ″ H CH3 OC2H5 CH5 ″ ″ ″ H OCH3 OCH3 N6 ″ ″ ″ H OCH3 CH3 N7 ″ ″ ″ H OCH3 Cl CH8 ″ ″ ″ H OCF2H CH3 CH9 ″ ″ ″ H OCF2H OCF2H CH10 ″ ″ ″ H OCH3 Br CH11 ″ ″ ″ H OCH3 OC2H5 CH12 ″ ″ ″ H OCH3 SCH3 CH13 ″ ″ ″ H OCH3 OC2H5 N14 ″ ″ ″ H OCH3 OC3H7 CH15 ″ ″ ″ H CH3 Cl CH16 ″ ″ ″ H Cl OC2H5 CH17 ″ ″ ″ H OC2H5 OC2H5 CH18 ″ ″ ″ H C2H5 OCH3 CH19 ″ ″ ″ H CF3 OCH3 CH20 ″ ″ ″ H OCH2CF3 CH3 CH21 ″ ″ ″ H OCH2CF3 OCH3 CH22 ″ ″ ″ H OCH2CF3 OCH2CF3 CH23 ″ ″ ″ H OCH2CF3 OCH3 N24 ″ ″ ″ H OCH3 CH(OCH3)2CH Vb. R1 R4 R5 R7 X Y Z Fp.℃25 ″ ″ ″ CH3 OCH3 OCH3 CH26 ″ ″ ″ CH3 OCH3 CH3 N27 ″ H COCH3 H OCH3 OCH3 CH28 ″ ″ ″ H OCH3 CH3 CH29 ″ ″ ″ H CH3 CH3 CH30 ″ ″ ″ H CH3 OC2H5 CH31 ″ ″ ″ H OCH3 OCH3 N32 ″ ″ ″ H OCH3 CH3 N33 ″ ″ ″ H OCH3 Cl CH34 ″ ″ ″ H OCF2H CH3 CH35 ″ ″ ″ H OCF2H OCF2H CH36 ″ ″ ″ H OCH3 Br CH37 ″ ″ ″ H OCH3 OC2H5 CH38 ″ ″ ″ H OCH3 SCH3 CH39 ″ ″ ″ H OCH3 OC2H5 N40 ″ ″ ″ H OCH3 OC3H7 CH41 ″ ″ ″ H CH3 Cl CH42 ″ ″ ″ H Cl OC2H5 CH43 ″ ″ ″ H OC2H5 OC2H5 CH44 ″ ″ ″ H C2H5 OCH3 CH45 ″ ″ ″ H CF3 OCH3 CH46 ″ ″ ″ H OCH2CF3 CH3 CH47 ″ ″ ″ H OCH2CF3 OCH3 CH48 ″ ″ ″ H OCH2CF3 OCH2CF3 CH49 ″ ″ ″ H OCH2CF3 OCH3 N50 ″ ″ ″ H OCH3 CH(OCH3)2CH51 ″ ″ ″ CH3 OCH3 OCH3 CH52 ″ ″ ″ CH3 OCH3 CH3 N53 ″ CH3 CHO H OCH3 OCH3 CH 150-15154 ″ ″ ″ H OCH3 CH3 CH55 ″ ″ ″ H CH3 CH3 CH56 ″ ″ ″ H CH3 OC2H5 CH57 ″ ″ ″ H OCH3 OCH3 N58 ″ ″ ″ H OCH3 CH3 N59 ″ ″ ″ H OCH3 Cl CH Vb. R1 R4 R5 R7 X Y Z Fp.℃60 ″ ″ ″ H OCF2H CH3 CH61 ″ ″ ″ H OCF2H OCF2H CH62 ″ ″ ″ H OCH3 Br CH63 ″ ″ ″ H OCH3 OC2H5 CH64 ″ ″ ″ H OCH3 SCH3 CH65 ″ ″ ″ H OCH3 OC2H5 N66 ″ ″ ″ H OCH3 OC3H7 CH67 ″ ″ ″ H CH3 Cl CH68 ″ ″ ″ H Cl OC2H5 CH69 ″ ″ ″ H OC2H5 OC2H5 CH70 ″ ″ ″ H C2H5 OCH3 CH71 ″ ″ ″ H CF3 OCH3 CH72 ″ ″ ″ H OCH2CF3 CH3 CH73 ″ ″ ″ H OCH2CF3 OCH3 CH74 ″ ″ ″ H OCH2CF3 OCH2CF3 CH75 ″ ″ ″ H OCH2CF3 OCH3 N76 ″ ″ ″ H OCH3 CH(OCH3)2 CH77 ″ ″ ″ CH3 OCH3 OCH3 CH78 ″ ″ ″ CH3 OCH3 CH3 N79 ″ CH3 COCH3H OCH3 OCH3 CH80 ″ ″ ″ H OCH3 CH3 CH81 ″ ″ ″ H CH3 CH3 CH82 ″ ″ ″ H CH3 OC2H5 CH83 ″ ″ ″ H OCH3 OCH3 N84 ″ ″ ″ H OCH3 CH3 N85 ″ ″ ″ H OCH3 Cl CH86 ″ ″ ″ H OCF2H CH3 CH87 ″ ″ ″ H OCF2H OCF2H CH88 ″ ″ ″ H OCH3 Br CH89 ″ ″ ″ H OCH3 OC2H5 CH90 ″ ″ ″ H OCH3 SCH3 CH91 ″ ″ ″ H OCH3 OC2H5 N92 ″ ″ ″ H OCH3 OC3H7 CH93 ″ ″ ″ H CH3 Cl CH94 ″ ″ ″ H Cl OC2H5 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃95 ″ ″ ″ H OC2H5 OC2H5 CH96 ″ ″ ″ H C2H5 OCH3 CH97 ″ ″ ″ H CF3 OCH3 CH98 ″ ″ ″ H OCH2CF3 CH3 CH99 ″ ″ ″ H OCH2CF3 OCH3 CH100 ″ ″ ″ H OCH2CF3 OCH2CF3 CH101 ″ ″ ″ H OCH2CF3 OCH3 N102 ″ ″ ″ H OCH3 CH(OCH3)2 CH103 ″ ″ ″ CH3 OCH3 OCH3 CH104 ″ ″ ″ CH3 OCH3 CH3 N105 ″ H SO2CH3H OCH3 OCH3 CH106 ″ ″ ″ H OCH3 CH3 CH107 ″ ″ ″ H CH3 CH3 CH108 ″ ″ ″ H OCH3 OCH3 N109 ″ ″ ″ H OCH3 CH3 N110 ″ ″ ″ H OC2H5 NHCH3 N111 ″ ″ ″ CH3 OCH3 OCH3 CH112 ″ ″ ″ CH3 OCH3 CH3 N113 ″ CH3 SO2CH3H OCH3 OCH3 CH114 ″ ″ ″ H OCH3 CH3 CH115 ″ ″ ″ H CH3 CH3 CH116 ″ ″ ″ H OCH3 OCH3 N117 ″ ″ ″ H OCH3 CH3 N118 ″ ″ ″ H OC2H5 NHCH3 N119 ″ ″ ″ CH3 OCH3 OCH3 CH120 ″ ″ ″ CH3 OCH3 CH3 N121 ″ OH CHO H OCH3 OCH3 CH122 ″ ″ ″ H OCH3 CH3 CH123 ″ ″ ″ H CH3 CH3 CH124 ″ ″ ″ H OCH3 OCH3 N125 ″ ″ ″ H OCH3 CH3 N126 ″ ″ ″ H OC2H5 NHCH3 N127 ″ ″ ″ CH3 OCH3 OCH3 CH128 ″ ″ ″ CH3 OCH3 CH3 N129 ″ OCH3 CHO H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃130 ″ ″ ″ H OCH3 CH3 CH131 ″ ″ ″ H CH3 CH3 CH132 ″ ″ ″ H OCH3 OCH3 N133 ″ ″ ″ H OCH3 CH3 N134 ″ ″ ″ H OC2H5 NHCH3 N135 ″ ″ ″ CH3 OCH3 OCH3 CH136 ″ ″ ″ CH3 OCH3 CH3 N137 ″ OH COCH3 H OCH3 OCH3 CH138 ″ ″ ″ H OCH3 CH3 CH139 ″ ″ ″ H CH3 CH3 CH140 ″ ″ ″ H OCH3 OCH3 N141 ″ ″ ″ H OCH3 CH3 N142 ″ ″ ″ H OC2H5 NHCH3 N143 ″ ″ ″ CH3 OCH3 OCH3 CH144 ″ ″ ″ CH3 OCH3 CH3 N145 ″ OCH3 COCH3 H OCH3 OCH3 CH146 ″ ″ ″ H OCH3 CH3 CH147 ″ ″ ″ H CH3 CH3 CH148 ″ ″ ″ H OCH3 OCH3 N149 ″ ″ ″ H OCH3 CH3 N150 ″ ″ ″ H OC2H5 NHCH3 N151 ″ ″ ″ CH3 OCH3 OCH3 CH152 ″ ″ ″ CH3 OCH3 CH3 N153 ″ H COC2H5 H OCH3 OCH3 CH154 ″ ″ ″ H OCH3 CH3 CH155 ″ ″ ″ H OCH3 OCH3 N156 ″ ″ ″ H OCH3 CH3 N157 ″ CH3 ″ H OCH3 OCH3 CH158 ″ ″ ″ H OCH3 CH3 CH159 ″ ″ ″ H OCH3 OCH3 N160 ″ ″ ″ H OCH3 CH3 N161 ″ H COCH2OCH3H OCH3 OCH3 CH162 ″ ″ ″ H OCH3 CH3 CH163 ″ ″ ″ H OCH3 OCH3 N164 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃165 ″ CH3 ″ H OCH3 OCH3 CH166 ″ ″ ″ H OCH3 CH3 CH167 ″ ″ ″ H OCH3 OCH3 N168 ″ ″ ″ H OCH3 CH3 N169 ″ H COCO2C2H5H OCH3 OCH3 CH170 ″ ″ ″ H OCH3 CH3 CH171 ″ ″ ″ H OCH3 OCH3 N172 ″ ″ ″ H OCH3 CH3 N173 ″ CH3 ″ H OCH3 OCH3 CH174 ″ ″ ″ H OCH3 CH3 CH175 ″ ″ ″ H OCH3 OCH3 N176 ″ ″ ″ H OCH3 CH3 N177 ″ H COCF3 H OCH3 OCH3 CH178 ″ ″ ″ H OCH3 CH3 CH179 ″ ″ ″ H OCH3 OCH3 N180 ″ ″ ″ H OCH3 CH3 N181 ″ CH3 ″ H OCH3 OCH3 CH182 ″ ″ ″ H OCH3 CH3 CH183 ″ ″ ″ H OCH3 OCH3 N184 ″ ″ ″ H OCH3 CH3 N185 ″ H COOCH3 H OCH3 OCH3 CH186 ″ ″ ″ H OCH3 CH3 CH187 ″ ″ ″ H OCH3 OCH3 N188 ″ ″ ″ H OCH3 CH3 N189 ″ CH3 ″ H OCH3 OCH3 CH190 ″ ″ ″ H OCH3 CH3 CH191 ″ ″ ″ H OCH3 OCH3 N192 ″ ″ ″ H OCH3 CH3 N193 ″ H CONHC2H5 H OCH3 OCH3 CH194 ″ ″ ″ H OCH3 CH3 CH195 ″ ″ ″ H OCH3 OCH3 N196 ″ ″ ″ H OCH3 CH3 N197 ″ CH3 ″ H OCH3 OCH3 CH198 ″ ″ ″ H OCH3 CH3 CH199 ″ ″ ″ H OCH3 OCH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃200 ″ ″ ″ H OCH3 CH3 N201 ″ H CSNHC2H5 H OCH3 OCH3 CH202 ″ ″ ″ H OCH3 CH3 CH203 ″ ″ ″ H OCH3 OCH3 N204 ″ ″ ″ H OCH3 CH3 N205 ″ CH3 ″ H OCH3 OCH3 CH206 ″ ″ ″ H OCH3 CH3 CH207 ″ ″ ″ H OCH3 OCH3 N208 ″ ″ ″ H OCH3 CH3 N209 ″ H SO2NHCH3 H OCH3 OCH3 CH210 ″ ″ ″ H OCH3 CH3 CH211 ″ ″ ″ H OCH3 OCH3 N212 ″ ″ ″ H OCH3 CH3 N213 ″ CH3 ″ H OCH3 OCH3 CH214 ″ ″ ″ H OCH3 CH3 CH215 ″ ″ ″ H OCH3 OCH3 N216 ″ ″ ″ H OCH3 CH3 N217 ″ H SO2N(CH3)2H OCH3 OCH3 CH218 ″ ″ ″ H OCH3 CH3 CH219 ″ ″ ″ H OCH3 OCH3 N220 ″ ″ ″ H OCH3 CH3 N221 ″ CH3 ″ H OCH3 OCH3 CH222 ″ ″ ″ H OCH3 CH3 CH223 ″ ″ ″ H OCH3 OCH3 N224 ″ ″ ″ H OCH3 CH3 N225 ″ -CH2CH2CH2CO- H OCH3 OCH3 CH226 ″ ″ H OCH3 CH3 CH227 ″ ″ H OCH3 OCH3 N228 ″ ″ H OCH3 CH3 N229 ″ -CH2CH2CH2SO2- H OCH3 OCH3 CH230 ″ ″ H OCH3 CH3 CH231 ″ ″ H OCH3 OCH3 N232 ″ ″ H OCH3 CH3 N233 ″ -CH2CH2CH2CH2CO- H OCH3 OCH3 CH234 ″ ″ H CH3 CH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃235 ″ ″ H OCH3 OCH3 N236 ″ ″ H OCH3 CH3 N237 ″ -CH2CH2CH2CH2SO2-H OCH3 OCH3 CH238 ″ ″ H OCH3 CH3 CH239 ″ ″ H OCH3 OCH3 N240 ″ ″ H OCH3 CH3 N241 ″ -CH2CH2OCH2CH2- H OCH3 OCH3 CH242 ″ ″ H OCH3 CH3 CH243 ″ ″ H OCH3 OCH3 N244 ″ ″ H OCH3 CH3 N245 ″ H COC3H7 H OCH3 OCH3 CH246 ″ ″ ″ H OCH3 CH3 CH247 ″ ″ ″ H OCH3 OCH3 N248 ″ ″ ″ H OCH3 CH3 N249 ″ CH3 ″ H OCH3 OCH3 CH250 ″ ″ ″ H OCH3 CH3 CH251 ″ ″ ″ H OCH3 OCH3 N252 ″ ″ ″ H OCH3 CH3 N253 ″ H COCH2Cl H OCH3 OCH3 CH254 ″ ″ ″ H OCH3 CH3 CH255 ″ ″ ″ H OCH3 OCH3 N256 ″ ″ ″ H OCH3 CH3 N257 ″ CH3 ″ H OCH3 OCH3 CH258 ″ ″ ″ H OCH3 CH3 CH259 ″ ″ ″ H OCH3 OCH3 N260 ″ ″ ″ H OCH3 CH3 N261 ″ H COCHCl2 H OCH3 OCH3 CH262 ″ ″ ″ H OCH3 CH3 CH263 ″ ″ ″ H OCH3 OCH3 N264 ″ ″ ″ H OCH3 CH3 N265 ″ CH3 ″ H OCH3 OCH3 CH266 ″ ″ ″ H OCH3 CH3 CH267 ″ ″ ″ H OCH3 OCH3 N268 ″ ″ ″ H OCH3 CH3 N269 ″ H COCCl3 H OCH3 OCH3 CH Vb R1 R4 R5 R7 X Y Z Fp℃270 ″ ″ ″ H OCH3 CH3 CH271 ″ ″ ″ H OCH3 OCH3 N272 ″ ″ ″ H OCH3 CH3 N273 ″ CH3 ″ H OCH3 OCH3 CH274 ″ ″ ″ H OCH3 CH3 CH275 ″ ″ ″ H OCH3 OCH3 N276 ″ ″ ″ H OCH3 CH3 N277 ″ H COCH＝CH2 H OCH3 OCH3 CH278 ″ ″ ″ H OCH3 CH3 CH279 ″ ″ ″ H OCH3 OCH3 N280 ″ ″ ″ H OCH3 CH3 N281 ″ CH3 ″ H OCH3 OCH3 CH282 ″ ″ ″ H OCH3 CH3 CH283 ″ ″ ″ H OCH3 OCH3 N284 ″ ″ ″ H OCH3 CH3 N285 ″ H COC＝CH H OCH3 OCH3 CH286 ″ ″ ″ H OCH3 CH3 CH287 ″ ″ ″ H OCH3 OCH3 N288 ″ ″ ″ H OCH3 CH3 N289 ″ CH3 ″ H OCH3 OCH3 CH290 ″ ″ ″ H OCH3 CH3 CH291 ″ ″ ″ H OCH3 OCH3 N292 ″ ″ ″ H OCH3 CH3 N293 ″ H COC6H5 H OCH3 OCH3 CH294 ″ ″ ″ H OCH3 CH3 CH295 ″ ″ ″ H OCH3 OCH3 N296 ″ ″ ″ H OCH3 CH3 N297 ″ CH3 ″ H OCH3 OCH3 CH298 ″ ″ ″ H OCH3 CH3 CH299 ″ ″ ″ H OCH3 OCH3 N300 ″ ″ ″ H OCH3 CH3 N301 ″ SO2C6H5 SO2C6H5H OCH3 OCH3 CH302 ″ ″ ″ H OCH3 CH3 CH303 ″ ″ ″ H OCH3 OCH3 N304 ″ ″ ″ H OCH3 CH3 N Vb R1 R4 R5 R7 X Y Z Fp.℃305 ″ SO2CH3 SO2CH3 H OCH3 OCH3 CH306 ″ ″ ″ H OCH3 CH3 CH307 ″ ″ ″ H OCH3 OCH3 N308 ″ ″ ″ H OCH3 CH3 N309 ″ H COCH2Br H OCH3 OCH3 CH310 ″ ″ ″ H OCH3 CH3 N311 ″ CH3 ″ H OCH3 OCH3 CH312 ″ ″ ″ H OCH3 CH3 N313 ″ H COCH2F H OCH3 OCH3 CH314 ″ ″ ″ H OCH3 CH3 N315 ″ CH3 ″ H OCH3 OCH3 CH316 ″ ″ ″ H OCH3 CH3 N317 ″ H COCH2C＝CH H OCH3 OCH3 CH318 ″ ″ ″ H OCH3 CH3 N319 ″ CH3 ″ H OCH3 OCH3 CH320 ″ ″ ″ H OCH3 CH3 N321 ″ H COCO2CH3 H OCH3 OCH3 CH322 ″ ″ ″ H OCH3 CH3 N323 ″ CH3 ″ H OCH3 OCH3 CH324 ″ ″ ″ H OCH3 CH3 N325 ″ H CO2C2H5 H OCH3 OCH3 CH326 ″ ″ ″ H OCH3 CH3 N327 ″ CH3 ″ H OCH3 OCH3 CH328 ″ ″ ″ H OCH3 CH3 N329 ″ H COSCH3 H OCH3 OCH3 CH330 ″ ″ ″ H OCH3 CH3 N331 ″ CH3 ″ H OCH3 OCH3 CH332 ″ ″ ″ H OCH3 CH3 N333 ″ H CSOCH3 H OCH3 OCH3 CH334 ″ ″ ″ H OCH3 CH3 N335 ″ CH3 ″ H OCH3 OCH3 CH336 ″ ″ ″ H OCH3 CH3 N337 ″ H CSSCH3 H OCH3 OCH3 CH338 ″ ″ ″ H OCH3 CH3 N339 ″ CH3 ″ H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp.℃340 ″ ″ ″ H OCH3 CH3 N341 ″ H COCH(CH3)2 H OCH3 OCH3 CH342 ″ ″ ″ H OCH3 CH3 N343 ″ CH3 ″ H OCH3 OCH3 CH344 ″ ″ ″ H OCH3 CH3 N345 ″ H COC(CH3)3 H OCH3 OCH3 CH346 ″ ″ ″ H OCH3 CH3 N347 ″ CH3 ″ H OCH3 OCH3 CH348 ″ ″ ″ H OCH3 CH3 N349 ″ H CO-环丙基 H OCH3 OCH3 CH350 ″ ″ ″ H OCH3 CH3 N351 ″ CH3 ″ H OCH3 OCH3 CH352 ″ ″ ″ H OCH3 CH3 N353 ″ H CO-环丁基 H OCH3 OCH3 CH354 ″ ″ ″ H OCH3 CH3 N355 ″ CH3 ″ H OCH3 OCH3 CH356 ″ ″ ″ H OCH3 CH3 N357 ″ H CO-环戊基 H OCH3 OCH3 CH358 ″ ″ ″ H OCH3 CH3 N359 ″ CH3 ″ H OCH3 OCH3 CH360 ″ ″ ″ H OCH3 CH3 N361 ″ H CO-环己基 H OCH3 OCH3 CH362 ″ ″ ″ H OCH3 CH3 N363 ″ CH3 ″ H OCH3 OCH3 CH364 ″ ″ ″ H OCH3 CH3 N365 ″ H CONHCH2CH2Cl H OCH3 OCH3 CH366 ″ ″ ″ H OCH3 CH3 N367 ″ CH3 ″ H OCH3 OCH3 CH368 ″ ″ ″ H OCH3 CH3 N369 ″ H CSNHCH2CH2Cl H OCH3 OCH3 CH370 ″ ″ ″ H OCH3 CH3 N371 ″ CH3 ″ H OCH3 OCH3 CH372 ″ ″ ″ H OCH3 CH3 N373 ″ H CONH-n-C4H9 H OCH3 OCH3 CH374 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃375 ″ CH3 ″ H OCH3 OCH3 CH376 ″ ″ ″ H OCH3 CH3 N377 ″ H CSNHCH3 H OCH3 OCH3 CH378 ″ ″ ″ H OCH3 CH3 N379 ″ CH3 ″ H OCH3 OCH3 CH380 ″ ″ ″ H OCH3 CH3 N381 ″ H CSNHCH2CH＝CH2H OCH3 OCH3 CH382 ″ ″ ″ H OCH3 CH3 N383 ″ CH3 ″ H OCH3 OCH3 CH384 ″ ″ ″ H OCH3 CH3 N385 ″ CH3 CSNHCH2COCH3 H OCH3 OCH3 CH386 ″ ″ ″ H OCH3 CH3 N387 ″ CH3 CSNHCH2COC2H5H OCH3 OCH3 CH388 ″ ″ ″ H OCH3 CH3 N389 ″ CH3 CONHCH2COCH3 H OCH3 OCH3 CH390 ″ ″ ″ H OCH3 CH3 N391 ″ CH3 CONHCH2COC2H5H OCH3 OCH3 CH392 ″ ″ ″ H OCH3 CH3 N393 ″ -CONHCH2CO- H OCH3 OCH3 CH394 ″ ″ H OCH3 CH3 N395 ″ H SO2CH2F H OCH3 OCH3 CH396 ″ ″ ″ H OCH3 CH3 N397 ″ CH3 ″ H OCH3 OCH3 CH398 ″ ″ ″ H OCH3 CH3 N399 ″ H SO2CF3 H OCH3 OCH3 CH400 ″ ″ ″ H OCH3 CH3 N401 ″ CH3 ″ H OCH3 OCH3 CH402 ″ ″ ″ H OCH3 CH3 N403 ″ H SO2C2H5 H OCH3 OCH3 CH404 ″ ″ ″ H OCH3 CH3 N405 ″ CH3 ″ H OCH3 OCH3 CH406 ″ ″ ″ H OCH3 CH3 N407 ″ H SO2-n-C3H7 H OCH3 OCH3 CH408 ″ ″ ″ H OCH3 CH3 N409 ″ CH3 ″ H OCH3 OCH3 CH Vb. R1 R4 R5 R7 X Y Z Fp℃410 ″ ″ H OCH3 CH3 N411 ″ OH COC2H5 H OCH3 OCH3 CH412 ″ ″ ″ H OCH3 CH3 N413 ″ OCH3 ″ H OCH3 OCH3 CH414 ″ ″ ″ H OCH3 CH3 N415 ″ OH COCH2Cl H OCH3 OCH3 CH416 ″ ″ ″ H OCH3 CH3 N417 ″ OCH3 ″ H OCH3 OCH3 CH418 ″ ″ ″ H OCH3 CH3 N419 ″ OH COCF3 H OCH3 OCH3 CH420 ″ ″ ″ H OCH3 CH3 N421 ″ OCH3 ″ H OCH3 OCH3 CH422 ″ ″ ″ H OCH3 CH3 N423 ″ OH COCH2OCH3 H OCH3 OCH3 CH424 ″ ″ ″ H OCH3 CH3 N425 ″ OCH3 ″ H OCH3 OCH3 CH426 ″ ″ ″ H OCH3 CH3 N427 ″ OH COCO2C2H5 H OCH3 OCH3 CH428 ″ ″ ″ H OCH3 CH3 N429 ″ OCH3 ″ H OCH3 OCH3 CH430 ″ ″ ″ H OCH3 CH3 N431 ″ OH COOCH3 H OCH3 OCH3 CH432 ″ ″ ″ H OCH3 CH3 N433 ″ OCH3 ″ H OCH3 OCH3 CH434 ″ ″ ″ H OCH3 CH3 N435 ″ OH 环丙基 H OCH3 OCH3 CH436 ″ ″ ″ H OCH3 CH3 N437 ″ OCH3 ″ H OCH3 OCH3 CH438 ″ ″ ″ H OCH3 CH3 N439 ″ OH COC6H5 H OCH3 OCH3 CH440 ″ ″ ″ H OCH3 CH3 N441 ″ OCH3 ″ H OCH3 OCH3 CH442 ″ ″ ″ H OCH3 CH3 N443 ″ OH COCH(CH3)2 H OCH3 OCH3 CH444 ″ ″ ″ H OCH3 CH3 N Vb. R1 R4 R5 R7 X Y Z Fp.℃445 ″ OCH3 ″ H OCH3 OCH3 CH446 ″ ″ ″ H OCH3 CH3 N447 ″ OH COCH＝CH2 H OCH3 OCH3 CH448 ″ ″ ″ H OCH3 CH3 N449 ″ OCH3 ″ H OCH3 OCH3 CH450 ″ ″ ″ H OCH3 CH3 N451 ″ OH COCH＝CH H OCH3 OCH3 CH452 ″ ″ ″ H OCH3 CH3 N453 ″ OCH3 ″ H OCH3 OCH3 CH454 ″ ″ ″ H OCH3 CH3 N455 ″ OH SO2CH3 H OCH3 OCH3 CH456 ″ ″ ″ H OCH3 CH3 N457 ″ OCH3 ″ H OCH3 OCH3 CH458 ″ ″ ″ H OCH3 CH3 N459 ″ OH SO2NHCH3 H OCH3 OCH3 CH460 ″ ″ ″ H OCH3 CH3 N461 ″ OCH3 ″ H OCH3 OCH3 CH462 ″ ″ ″ H OCH3 CH3 N463 ″ OH SO2N(CH3)2H OCH3 OCH3 CH464 ″ ″ ″ H OCH3 CH3 N465 ″ OCH3 ″ H OCH3 OCH3 CH466 ″ ″ ″ H OCH3 CH3 N467 ″ C2H5CHO H OCH3 OCH3 CH468 ″ ″ ″ H OCH3 CH3 N469 ″ ″ COCH3 H OCH3 OCH3 CH470 ″ ″ ″ H OCH3 CH3 N471 ″ ″ 环丙基 H OCH3 OCH3 CH472 ″ ″ ″ H OCH3 CH3 N473 ″ ″ COCH2Cl H OCH3 OCH3 CH474 ″ ″ ″ H OCH3 CH3 N475 ″ ″ COCF3 H OCH3 OCH3 CH476 ″ ″ ″ H OCH3 CH3 N477 ″ ″ COOCH3 H OCH3 OCH3 CH478 ″ ″ ″ H OCH3 CH3 N479 ″ ″ COC6H5 H OCH3 OCH3 CH Vb R1 R4 R5 R7 X Y Z Fp℃480 ″ ″ ″ H OCH3 CH3 N481 ″ ″ CONHC2H5 H OCH3 OCH3 CH482 ″ ″ ″ H OCH3 CH3 N483 ″ ″ CSNHC2H5 H OCH3 OCH3 CH484 ″ ″ ″ H OCH3 CH3 N485 ″ ″ SO2CH3 H OCH3 OCH3 CH486 ″ ″ ″ H OCH3 CH3 N487 ″ ″ SO2NHCH3 H OCH3 OCH3 CH488 ″ ″ ″ H OCH3 CH3 N489 ″ ″ SO2N(CH3)2H OCH3 OCH3 CH490 ″ ″ ″ H OCH3 CH3 N491 ″ ″ SO2C6H5 H OCH3 OCH3 CH492 ″ ″ ″ H OCH3 CH3 N493 CO2C2H5 H CHO H OCH3 OCH3 CH494 ″ ″ ″ H OCH3 CH3 N495 ″ ″ COCH3 H OCH3 OCH3 CH496 ″ ″ ″ H OCH3 CH3 N497 ″ ″ SO2CH3 H OCH3 OCH3 CH498 ″ ″ ″ H OCH3 CH3 N499 ″ CH3 CHO H OCH3 OCH3 CH500 ″ ″ ″ H OCH3 CH3 N501 ″ ″ COCH3 H OCH3 OCH3 CH502 ″ ″ ″ H OCH3 CH3 N503 ″ ″ SO2CH3 H OCH3 OCH3 CH504 ″ ″ ″ H OCH3 CH3 N505 ″ C2H5CHO H OCH3 OCH3 CH506 ″ ″ ″ H OCH3 CH3 N507 ″ ″ COCH3 H OCH3 OCH3 CH508 ″ ″ ″ H OCH3 CH3 N509 ″ ″ SO2CH3 H OCH3 OCH3 CH510 ″ ″ ″ H OCH3 CH3 N511 ″ OH CHO H OCH3 OCH3 CH512 ″ ″ ″ H OCH3 CH3 N513 ″ ″ COCH3 H OCH3 OCH3 CH514 ″ ″ ″ H OCH3 CH3 N Vb R1 R4 R5 R7 X Y Z Fp℃515 ″ ″ SO2CH3 H OCH3 OCH3 CH516 ″ ″ ″ H OCH3 CH3 N517 ″ OCH3 CHO H OCH3 OCH3 CH518 ″ ″ ″ H OCH3 CH3 N519 ″ ″ COCH3 H OCH3 OCH3 CH520 ″ ″ ″ H OCH3 CH3 N521 COO-n-Bu H CHO H ″ OMe CH522 CONMe2 Me ″ H ″ Me N523 CONHMe H ″ H ″ OMe CH524 CO-SMe Me CO-Me H ″ Me N525 CO-OMe n-Bu CHO H ″ OMe CH526 ″ n-Bu ″ H ″ Me N527 ″ H ″ H OCH2CF3NMe2 N528 ″ Me ″ H ″ ″ N529 ″ H CO-Me H ″ ″ N530 ″ Me ″ H ″ ″ N531 ″ ″ SO2CH3 H OCH3 OCH3 CH532 ″ ″ ″ H OCH3 CH3 N533 CO2CH3 
H OCH3 OCH3 CH534 ″ ″ H OCH3 CH3 N
B.制剂实施例a)粉剂的制备是通过混合10重量份的式(I)化合物和90重量份惰性物质滑石并在锤磨中磨碎混合物。b)容易分散在水中的可湿性粉剂的制备是通过混合25重量份的式(I)化合物，64重量份惰性物质含高岭土石英，10重量份木质素磺酸钾和1重量份油酰基甲基牛磺酸钠作为湿润剂和分散剂，并在钉盘磨研磨混合物。c)容易分散在水中的浓悬浮液的制备是通过混合20重量份的式(I)化合物和6重量份的烷基酚聚乙二醇醚(riton X 207)，3重量份的异十三烷醇聚乙二醇醚(8EO)和71重量份石蜡矿物油(沸点范围例如大约255至277℃)，并在球磨中研磨混合物至细度小于5微米。d)可乳化浓缩液的制备是通过混合15重量份的式(I)化合物，75重量份的环己烷溶剂和10重量份乙氧基化的壬基酚乳化剂。e)水分散颗粒剂的制备是通过混合
75重量份 式(I)化合物
10重量份 木质素磺酸钙
5重量份 十二烷基硫酸钠
3重量份 聚乙烯醇和
7重量份 高岭土，在针盘磨(stiftmhle)中研磨混合物并通过喷入作为成粒流体的水于流动床上形成颗粒粉末。f)水分散性颗粒剂的制备还可通过在胶体磨中的匀化和预粉碎25重量份的式(I)化合物，5重量份 2，2’-二萘基甲烷-6，6’-二磺酸钠2重量份 牛酰基甲基牛磺酸钠
(oleoylmethyltaurinsaures Natrium)1重量份 聚乙烯醇17重量份 碳酸钙和50重量份 水，然后在珠磨中研磨混合物用单物质-喷嘴在喷雾塔中将所得悬浮液雾化，并干燥产品。C.生物实施例1.对杂草的苗前作用
将单子叶和双子叶杂草品种的种子或根茎放置于塑料盆中的沙质沃土中并用土盖上。然后将根据本发明式(I)化合物或其盐作为可湿性粉剂或乳化浓缩液的水悬浮液或乳液，以600至800l水/ha的施用剂量，按不同剂量施用到覆盖土的表面。
处理后，将盆放置在温室中并保持杂草生长的良好条件。试验期3至4周后，在供试植物萌发后，与未处理对照物比较，目测评价对植物的损害和对萌发的损害。如试验结果所示，根据本发明化合物对广谱的禾本科杂草和双子叶杂草具有好的苗前除草活性。例如表1中实施例1，27，53至55，58，59，79，105，113，129，145，153，177，181，185，189，213，217，221，253，257，421，425，429，433，437，445，457，461，465，467，485，487，535，至543，547，551至559，562，563，和565至578和表2中实施例1，27，53，79，153，161，169，177，181，185，253，261，269，341，349，365和373和表3中的实施例27和535和表4中的实施例53的化合物，以每公顷0.3Kg至0.005Kg活性物质的剂量施用，对有害植物如田白芥、繁缕、珍珠菊和多花黑麦草具有好的苗前作用。2.对杂草的苗后作用
将单子叶和双子叶杂草品种的种子或根茎放置于塑料盆中的沙质沃土中并用土盖上并使之在良好条件的温室中生长。播种3周后，处理三叶期的的植物。将根据本发明式(I)化合物或其盐作为可湿性粉剂或乳化浓缩液剂以不同的剂量，以600至800l水/ha施用剂量，施用到植物的绿色部分，其后在理想的生长条件下，将供试植物放置在温室中大约3至4周，与未处理对照物比较，目测评价制剂的活性。根据本发明制剂还对经济上重要的广谱的禾本科杂草和双子叶杂草具有好的苗后除草活性。例如表1中实施例1，27，53至55，58，59，79，105，113，129，145，153，177，181，185，189，213，217，221，253，257，421，425，429，433，437，445，457，461，465，467，485，487，535，至543，547，551至559，562，563，和565至578和表2中实施例1，27，53，79，153，161，169，177，181，185，253，261，269，341，349，365和373和表3中的实施例27和535和表4中的实施例53的化合物，以每公顷0.3Kg至0.005Kg活性物质的剂量施用，对有害植物如田白芥、繁缕、珍珠菊和多花黑麦草具有好的苗后作用。3.作物的耐药性
在进一步的温室试验中，将许多种作物和杂草的种子放置于砂质沃土中并用土覆盖。
按照1.中所述方法立即处理一些盆，并把其余盆放在温室中直到植物发育出二至三个真叶，然后如2.所述用不同剂量的根据本发明的式(I)化合物或其盐进行喷雾。
施药并放置在温室中四至五周后进行目测评价，结果显示甚至在高活性物质使用剂量下，根据本发明化合物在苗前-和苗后-使用对双子叶作物不会造成任何伤害，双子叶作物如大豆、棉花、油菜、糖甜菜和土豆。而且，一些物质甚至对禾本科作物无害，禾本科作物如大麦、小麦、黑麦、高粱、小米、玉米或水稻。因此，式(I)化合物或其盐在防治农作物中有害植物生长时具有高度的选择性。
Claims (9)
1.式(I)的化合物或其盐，
其中
R1为CO-Q-R8，
R2和R3各自独立为H或(C1-C4)烷基，
R4为H，未取代或被一或多个下组包括的基团取代的(C1-C8)
烷基，上述取代基团由卤素、(C1-C4)烷氧基、(C1-C4)
烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)烷基磺酰基、[(C1
-C4)烷氧基]羰基和CN组成，或为未被取代或被一至多个卤原
子取代的(C3-C6)链烯基，或为未被取代或被一至多个卤原子
取代的(C3-C6)链炔基，或为羟基，(C1-C4)烷氧基，[(C1-C4)
烷基]羰基或(C1-C4)烷基磺酰基，后三个基团各自未被取代或
在烷基部分被-或多个卤原子或被(C1-C4)烷氧基或(C1-
C4)烷硫基取代，或为苯基磺酰基，其中苯基是未被取代或取代的，
R5为(C1-C4)烷基磺酰基或(C3-C6)链烯基磺酰基，后两
个基团各自未被取代或被一至多个卤原子或被(C1-C4)烷氧基
或(C1-C4)烷硫基取代的，或为苯基磺酰基或苯基羰基，后两
个基团的苯基各自未被取代或被取代，或为单-或二-[(C1-
C4)烷基]氨基磺酰基或[(C1-C6)烷基]羰基，后三个基团各自未被取
代或被一或多个下述基团取代，上述取代基由卤素、(C1-C4)
烷氧基、(C1-C4)烷硫基、(C1-C4)烷基亚磺酰基、(C1
-C4)烷基磺酰基、[(C1-C4)烷基]羰基、[(C1-C4)烷氧
基]羰基和CN组成，或为甲酰基，式-CO-CO-R’的基团
其中R’＝H，OH，(C1-C4)烷氧基或(C1-C4)烷基，
或为[(C3-C6)环烷基]羰基，[(C2-C6)链烯基]羰基或[(C2-C6)链炔基]
羰基，后三个基团各自未被取代或被一或多个卤原子取代，或为下
式的基团
或
R4和R5一起为是(-CH2)mB-或-B1-(CH2)ml-B-，
上述链是未被取代或被一个或多个(C1-C3)烷基取代和m为3
或4或m1为2或3，和
W为氧或硫原子，
B和B1各自独立为SO2或CO，
Q为O，S或-NR13-，
T为O或S，
R6为H，(C1-C4)烷基，(C1-C4)烷氧基，[(C1-C4)
烷基]羰基或[(C1-C4)烷氧基]羰基，后四个基团各自未被取代
或在烷基部分被一至多个卤原子取代，或为卤素，NO2或CN，
R7为H或CH3，
R8为H，(C1-C4)烷基，(C3-C4)链烯基或(C3-C4)
链炔基，后三个基团各自未被取代或被一或多个选自由卤素、(C1
-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和
[(C1-C4)烷氧基]羰基组成的一组基团取代，
R9为(C1-C4)烷基，(C3-C4)链烯基或(C3-C4)链炔
基，后三个基团各自未被取代或被一或多个选自由卤素、(C1-
C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)烷基]羰基和[(C1
-C4)烷氧基]羰基组成的一组基团取代，
R10和R11各自独立地为H，(C1-C4)烷基，(C3-C4)链烯
基或(C3-C4)链炔基，后三个基团各自未被取代或被一或多个
由卤素、(C1-C4)烷氧基、(C1-C4)烷硫基、[(C1-C4)
烷基]羰基和[(C1-C4)烷氧基]羰基组成的一组基团取代，
R12基团与氮原子一起为5或6元杂环，上述杂环在可能的氧化态
中可含有一个其它N，O和S杂原子，且是未被取代或被(C1-
C4)烷基或氧基取代，或被苯环稠和，
R13为H，(C1-C4)烷基，(C3-C4)链烯基或(C3-C4)
链炔基，后三个基团各自未被取代或被一或多个由卤素、(C1-
C4)烷氧基、(C1-C4)烷硫基组成的一组基团取代，
A为下式的基团
X和Y基团之一是氢，卤素，(C1-C3)烷基或(C1-C3)烷
氧基，后两个基团是未被取代或被卤素单取代或多取代或被(C1
-C3)烷氧基单取代，和
X和Y基团的另一个是氢，(C1-C3)烷基，(C1-C3)烷氧
基或(C1-C3)烷硫基，后三个含有烷基的基团是未被取代或被
卤原子单或多取代或被(C1-C3)烷氧基或(C1-C3)烷硫基
单取代或二取代，或为式NR14R15的基团，(C3-C6)环烷基，
(C2-C4)链烯基，(C2-C4)链炔基，(C3-C4)链烯氧
基，(C3-C4)链炔氧基，
Z为CH或N，
R14和R15各自彼此独立地为H，(C1-C3)烷基，(C3-C4)
链烯基，
X1为CH3、OCH3、OC2H5或OCHF2，
Y1为-O-或-CH2-
X2为CH3、C2H5或CH2CF3
Y2为OCH3、OC2H5、SCH3、SCH2CH3、CH3或C2H5
X3为CH3或OCH3，
Y3为H或CH3，
X4为CH3、OCH3、OC2H5、CH2OCH3或Cl，
Y4为CH3、OCH3、OC2H5或Cl和
Y5为CH3、C2H5、OCH3或Cl。
2.根据权利要求1的化合物及其盐，其中
R4为H，未取代或被一或多个下组包括的基团取代的(C1-C4)
烷基，上述取代基团由卤素、(C1-C4)烷氧基、(C1-C4)
烷硫基、(C1-C4)烷基磺酰基、[(C1-C4)烷氧基]羰基和
CN组成，或为(C3-C4)链烯基、(C3-C4)链炔基、羟基，
(C1-C4)烷氧基，[(C1-C4)烷基]羰基或(C1-C4)烷基磺酰
基，后五个基团各自未被取代或在烷基部分被一至多个卤原子取
代，或为苯基磺酰基，其中苯基是未被取代或被一或多个下述基团
取代的，取代基由卤素、(C1-C4)烷基和(C1-C4)烷氧基
组成，和
R5为(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、苯
基磺酰基或苯基羰基，后两个基团中的苯基各自未被取代或被一至
多个选自卤原子、(C1-C4)烷基和(C1-C4)烷氧基的基团
取代，或为单-或二-[(C1-C4)烷基]氨基磺酰基，未被取代
或被一或多个卤原子或(C1-C4)烷氧基或(C1-C4)烷硫基
取代的[(C1-C6)烷基]羰基，或为甲酰基、OHC-CO-、2-氧
-(C3-C5)链烷酰基、[(C1-C4)烷氧基]草酰基、[(C3-C6)
环烷基]羰基，[(C2-C4)链烯基]羰基或[(C2-C4)链炔基]羰基、或为下
式的基团
W为O或S
R6为H、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)
烷氧基、(C1-C4)卤代烷氧基或卤素，
R8各自为未被取代或被一或多个卤原子取代的(C1-C4)烷基，
或为(C3-C4)链烯基或(C3-C4)链炔基，
R9为H、未被取代或被一或多个卤原子或被(C1-C4)烷氧基、
(C1-C4)烷硫基、[(C1-C4)烷氧基]羰基和[(C1-C4)
烷基]羰基取代的(C1-C4)烷基，
R10和R11各自独立地为H、未被取代或被一或多个卤原子取代的
(C1-C4)烷基、或为(C3-C4)链烯基或(C3-C4)链炔
基、其中R10和R11至少一个不是氢，
R12基团与氮原子一起为5或6元杂环，上述杂环在不同的氧化态
中可含有一个其它N，O和S杂原子，且是未被取代或被(C1-
C4)烷基或氧基取代，
R13为H，未被取代或被一或多个由卤素原子取代的(C1-C4)
烷基、或为(C3-C4)链烯基或(C3-C4)链炔基。
3.根据权利要求1或2的化合物及其盐，其中
R4为H、(C1-C4)烷基、羟基或(C1-C4)烷氧基，
R5为(C1-C4)烷基磺酰基、CHO、未被取代或被一或多个卤
原子取代的[(C1-C4)烷基]羰基、或为[(C1-C4)烷氧基]
草酰基、[(C3-C6)环烷基]羰基或下式的基团
其中
W，T和R9至R12如上面式(I)中的定义，
R6为H、(C1-C3)烷基、(C1-C3)烷氧基或卤素，
A为下式的基团
Z为CH或N，和
X和Y基团之一为卤素、(C1-C2)烷基、(C1-C2)烷氧基、
OCF2H、CF3或OCH2CF3和X和Y的另一个为(C1-C2)烷
基、(C1-C2)烷氧基或(C1-C2)卤代烷氧基。
4.根据权利要求1的式(I)化合物或其盐的制备方法，其中包括
a)式(II)的化合物与式(III)杂环氨基甲酸酯反应
R*-O-CO-NR7-A (III)
其中R*是必要时被取代的苯基或(C1-C4)烷基，或
b)式(IV)的苯基磺酰基氨基甲酸酯与式(V)的氨基杂环反应
H-NR7-A (V)
或
c)式(VI)的磺酰基异氰酸酯与式(V)H-NR7-A的氨基杂
环反应
或
d)在一个单釜反应中，首先在碱存在下使式(V)H-NR7-A
的氨基杂环化物与光气反应，然后反应的中间体与式(II)的苯
基磺酰胺反应，或
e)在碱存在下式(VII)的磺酰氯与其中M＝NH4、Na或K的
氰酸酯M-OCN以及式(V)H-NR7-A的氨基杂环化物反
应，
f)在碱存在下上述式(II)的磺酰胺与式(V’)的(硫代)异
氰酸酯反应
W＝C＝N-A (V’)，
在式(II)-(VII)和(V’)中的基团R1-R7、A或W如
在式(I)中的定义，在方法a)-e)中，最初获得的是W＝O的式
(I)化合物。
5.一种除草和植物生长调节剂组合物，其中包含至少一种根据权利
要求1至3的式(I)化合物或其盐和植物保护中常用的制剂助剂。
6.一种防治有害植物或调节植物生长的方法，其中包含施用有效量
的至少一种根据权利要求1至3的式(I)化合物或其盐于有害植
物或植物、其植物种子或其生长地。
7.根据权利要求1至3的式(I)化合物或其盐作为除草剂或植物
生长调节剂的用途。
8.式(II)化合物
其中R1至R6如权利要求1中式(I)的定义。
9.根据权利要求8的式(II)化合物的制备方法，其中包含采用类
似于已知的方法使式(XV)化合物反应以除去叔丁基保护基
式(XV)中R1至R6如式(II)中的定义。
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| CN102550585A (zh) * | 2012-01-16 | 2012-07-11 | 河北博嘉农业有限公司 | 甲基二磺隆复配除草剂 |
| CN102792958A (zh) * | 2011-05-23 | 2012-11-28 | 山东滨农科技有限公司 | 含有甲基二磺隆和唑嘧磺草胺的除草剂组合物 |
| CN102792960A (zh) * | 2011-05-23 | 2012-11-28 | 山东滨农科技有限公司 | 含有甲基二磺隆和氟啶嘧磺隆的除草剂组合物 |
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| CN102119701B (zh) * | 1996-12-07 | 2013-11-20 | 赫彻斯特-舍林农业发展有限公司 | 包含苯磺酰胺的除草组合物 |
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| DE19616445A1 (de) * | 1996-04-25 | 1997-11-06 | Hoechst Schering Agrevo Gmbh | Substituierte Aminomethylphenylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| DE19702200A1 (de) * | 1997-01-23 | 1998-07-30 | Hoechst Schering Agrevo Gmbh | Phenylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| DE19832017A1 (de) * | 1998-07-16 | 2000-01-27 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit substituierten Phenylsulfonylharnstoffen zur Unkrautbekämpfung in Reis |
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| DE10135642A1 (de) | 2001-07-21 | 2003-02-27 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen |
| DE10160139A1 (de) * | 2001-12-07 | 2003-06-18 | Bayer Cropscience Gmbh | Synergistische herbizide Mittel enthaltend bestimmte Herbizide aus der Gruppe der Benzoylcylohexandione |
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| EP1844654A1 (de) | 2006-03-29 | 2007-10-17 | Bayer CropScience GmbH | Penetrationsförderer für agrochemische Wirkstoffe |
| DE102007013362A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Cropscience Ag | Penetrationsförderer für herbizide Wirkstoffe |
| ITMI20062368A1 (it) * | 2006-12-11 | 2008-06-12 | Isagro Spa | Composizioni erbicide |
| EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| EP2193712A1 (de) | 2008-12-05 | 2010-06-09 | Bayer CropScience AG | Dispersionen enthaltend Inhibitoren der Hydroxyphenylpyruvat-Dioxygenase |
| WO2011076731A1 (de) | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Flüssige formulierung von 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamid |
| US10544426B2 (en) | 2010-10-15 | 2020-01-28 | Bayer Intellectual Property Gmbh | Methods of using ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant beta vulgaris plants |
| EP2713733B1 (en) | 2011-05-04 | 2018-03-14 | Bayer Intellectual Property GmbH | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants |
| DE102011079997A1 (de) | 2011-07-28 | 2012-09-13 | Bayer Corpscience Ag | Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Pyrazol-Insektizide als Safener |
| DE102011079991A1 (de) | 2011-07-28 | 2012-09-13 | Bayer Crop Science Ag | Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Nicotinoid-Insektizide als Safener |
| DE102011080020A1 (de) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Dicarboximid-Fungizide als Safener |
| DE102011080016A1 (de) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Strobilurin-Fungizide als Safener |
| DE102011080004A1 (de) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Carbamat-Fungizide als Safener |
| DE102011080001A1 (de) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Verwendung von Saatgutbehandlungs-Wirkstoffen aus der Gruppe der Carbamat-Insektizide als Safener |
| DE102011080007A1 (de) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Verwendung von Saatgutbehandlungs-Wirkstoffen aus den Gruppen der Conazole- und Triazol-Fungizide als Safener |
| DE102011080010A1 (de) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Verwendung von Saatgutbehandlungs-Wirkstoffen aus den Gruppen der Anilid- und Thiazol-Fungizide als Safener |
| ES2687545T5 (es) | 2012-12-13 | 2022-08-31 | Bayer Cropscience Ag | Uso de herbicidas inhibidores de ALS para el control de vegetación indeseada en plantas Beta vulgaris tolerantes a herbicidas inhibidores de ALS |
| UA118765C2 (uk) | 2013-08-09 | 2019-03-11 | Байєр Кропсайєнс Акцієнгезелльшафт | Третинні гербіцидні комбінації, що містять дві сульфонілсечовини |
| KR20160004095U (ko) | 2015-05-21 | 2016-11-30 | 이영재 | 전선연결구 |
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| CN116568137A (zh) | 2020-12-01 | 2023-08-08 | 拜耳公司 | 包含甲基二磺隆和tehp的组合物 |
| WO2022117515A1 (en) | 2020-12-01 | 2022-06-09 | Bayer Aktiengesellschaft | Compositions comprising iodosulfuron-methyl and tehp |
| GB202117598D0 (en) | 2021-12-06 | 2022-01-19 | Syngenta Crop Protection Ag | Herbicidal compositions |
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| CN119604194A (zh) | 2022-07-25 | 2025-03-11 | 先正达农作物保护股份公司 | 除草组合物 |
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| US4927453A (en) * | 1986-10-17 | 1990-05-22 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| WO1989010921A1 (en) * | 1988-05-12 | 1989-11-16 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| PH27460A (en) * | 1989-12-28 | 1993-07-09 | Kumiai Chemical Industry Co | Pyrimidine derivatives and herbicidal composition containing the same |
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1993
- 1993-10-15 DE DE4335297A patent/DE4335297A1/de not_active Withdrawn
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- 1994-10-12 CA CA002174127A patent/CA2174127C/en not_active Expired - Lifetime
- 1994-10-12 HU HU9600970A patent/HU215464B/hu unknown
- 1994-10-12 WO PCT/EP1994/003369 patent/WO1995010507A1/de active IP Right Grant
- 1994-10-12 DK DK94929539T patent/DK0723534T3/da active
- 1994-10-12 RU RU96109050/04A patent/RU2158732C2/ru active Protection Beyond IP Right Term
- 1994-10-12 EP EP94929539A patent/EP0723534B1/de not_active Expired - Lifetime
- 1994-10-12 RO RO96-00797A patent/RO118713B1/ro unknown
- 1994-10-12 ES ES94929539T patent/ES2122338T3/es not_active Expired - Lifetime
- 1994-10-12 PL PL94313971A patent/PL180011B1/pl unknown
- 1994-10-12 KR KR1019960701935A patent/KR100354312B1/ko not_active Expired - Lifetime
- 1994-10-12 CZ CZ19961083A patent/CZ290929B6/cs not_active IP Right Cessation
- 1994-10-12 CN CN94194137A patent/CN1057086C/zh not_active Expired - Lifetime
- 1994-10-12 AU AU78556/94A patent/AU698918B2/en not_active Expired
- 1994-10-12 JP JP51129095A patent/JP3920323B2/ja not_active Expired - Lifetime
- 1994-10-12 DE DE59406570T patent/DE59406570D1/de not_active Expired - Lifetime
- 1994-10-12 BR BR9407832A patent/BR9407832A/pt not_active IP Right Cessation
- 1994-10-12 UA UA96041429A patent/UA44714C2/uk unknown
- 1994-10-12 AT AT94929539T patent/ATE169006T1/de active
- 1994-10-13 US US08/322,610 patent/US5648315A/en not_active Expired - Lifetime
- 1994-10-14 ZA ZA948063A patent/ZA948063B/xx unknown
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1996
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- 1997-03-31 US US08/829,250 patent/US5925597A/en not_active Expired - Lifetime
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- 1999-02-01 US US09/241,213 patent/US6239306B1/en not_active Expired - Lifetime
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| CN100344612C (zh) * | 2000-07-24 | 2007-10-24 | 拜尔作物科学有限公司 | 经取代的磺酰氨基甲基苯甲酸（衍生物）及其制备方法 |
| CN102792958A (zh) * | 2011-05-23 | 2012-11-28 | 山东滨农科技有限公司 | 含有甲基二磺隆和唑嘧磺草胺的除草剂组合物 |
| CN102792960A (zh) * | 2011-05-23 | 2012-11-28 | 山东滨农科技有限公司 | 含有甲基二磺隆和氟啶嘧磺隆的除草剂组合物 |
| CN103404528A (zh) * | 2012-01-16 | 2013-11-27 | 河北博嘉农业有限公司 | 甲基二磺隆复配除草剂 |
| CN102550585A (zh) * | 2012-01-16 | 2012-07-11 | 河北博嘉农业有限公司 | 甲基二磺隆复配除草剂 |
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| CN103355336A (zh) * | 2013-07-30 | 2013-10-23 | 河北博嘉农业有限公司 | 氟磺隆复配的玉米田除草剂 |
| CN103524386A (zh) * | 2013-10-24 | 2014-01-22 | 滨海白云化工有限公司 | 2-氨基-4-甲磺酰胺甲基苯甲酸甲酯的制备方法 |
| CN103755603A (zh) * | 2014-01-28 | 2014-04-30 | 江苏省农用激素工程技术研究中心有限公司 | 2-氨基磺酰基-4-甲磺酰胺基甲基苯甲酸甲酯的制备方法 |
| CN106305749A (zh) * | 2016-08-15 | 2017-01-11 | 河南省莱恩坪安园林植保有限公司 | 一种结缕草中防治杂草的除草剂 |
| CN106305749B (zh) * | 2016-08-15 | 2019-01-25 | 河南省莱恩坪安园林植保有限公司 | 一种结缕草中防治杂草的除草剂 |
| CN114456120A (zh) * | 2021-12-24 | 2022-05-10 | 郑州手性药物研究院有限公司 | 双磺酰氨基取代的磺酰脲类化合物及其制备方法和应用 |
| CN114456120B (zh) * | 2021-12-24 | 2024-06-18 | 郑州手性药物研究院有限公司 | 双磺酰氨基取代的磺酰脲类化合物及其制备方法和应用 |
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