CN1143630A - 用作杀虫剂的二苯酮腙衍生物 - Google Patents
用作杀虫剂的二苯酮腙衍生物 Download PDFInfo
- Publication number
- CN1143630A CN1143630A CN96107424A CN96107424A CN1143630A CN 1143630 A CN1143630 A CN 1143630A CN 96107424 A CN96107424 A CN 96107424A CN 96107424 A CN96107424 A CN 96107424A CN 1143630 A CN1143630 A CN 1143630A
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- CN
- China
- Prior art keywords
- group
- carbonyl
- alkyl
- methyl
- hydrogen
- Prior art date
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- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical class C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 title abstract description 12
- 239000002917 insecticide Substances 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims description 2548
- 150000001875 compounds Chemical class 0.000 claims description 181
- -1 4Be hydrogen Chemical class 0.000 claims description 150
- 238000000034 method Methods 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 239000012442 inert solvent Substances 0.000 claims description 25
- 241000238631 Hexapoda Species 0.000 claims description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000011230 binding agent Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 10
- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 claims description 10
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005864 Sulphur Substances 0.000 claims description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 6
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 4
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006017 1-propenyl group Chemical group 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 230000002508 compound effect Effects 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- 125000001309 chloro group Chemical group Cl* 0.000 description 57
- 239000000243 solution Substances 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 37
- 239000012965 benzophenone Substances 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- 150000002576 ketones Chemical class 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229910020314 ClBr Inorganic materials 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 238000005406 washing Methods 0.000 description 16
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- 231100000225 lethality Toxicity 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 12
- 125000001246 bromo group Chemical group Br* 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 11
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 11
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 8
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000006837 decompression Effects 0.000 description 5
- 229940117389 dichlorobenzene Drugs 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 239000003208 petroleum Substances 0.000 description 5
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 5
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 4
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Abstract
式(I)代表的新的二苯酮腙衍生物,式中R1、R2、R3、R4、R5、R6、R7和n的定义见说明书。式(I)的二苯酮腙衍生物具有优良的杀虫活性。
Description
本发明涉及新的二苯酮腙衍生物及其制备方法和其作为杀虫剂的用途,还涉及制备它们的新中间体及其制备方法。
已知某些4-取代的-4’-烷磺酰氧基二苯酮腙衍生物具有杀虫活性(参见下列文献:British Crop Protection Conference Pests and Diseases1984,Vol.2,405-412;Japanese Patent Kokai Publications Sho 54-122261(=EP-3913-A,USP4394387);Sho 56-45452(=EP-26040-A,USP4331680,USP4432994);Hei 2-138246(=EP-355832-A,USP4980373);Hei 3-74356(DERWENT AN-91-136915);Hei 4-1173(DERWENT AN-92-053936);Hei 6-25134(=CA2094010);Hei 6-184079(=USP5340837,USP5405871);Hei 7-149708(=EP-647622);Hei 7-242618(=CA2139465)和Hei 7-247261(=DERWENT AN=95-363559))。
然而,这些已知化合物的活性水平和持续时间并不是在所有应用领域都完全满意,尤其是抗某些生物体或低浓度应用时。
现已发现下式(I)的新的二苯酮腙衍生物:其中R1是卤素;R2是氢或C1-4烷基;R3是氰基、任选地被取代的C1-4烷基、C2-4链烯基或C3-4炔基、C1-4烷基-羰基或C1-4烷氧基-硫代羰基;R4是氢、苯基、苄基、任选地被取代的C1-8烷基、任选地被取代的C2-8链烯基、-COR8、-CO-OR9或
;R5是氢、甲酰基、苯基、任选地被取代的C1-8烷基、任选地被取代的C2-8链烯基、任选地被取代的C3-8炔基、任选地被取代的C1-8烷基-羰基、任选地被取代的C1-6烷基-草酰基、任选地被取代的C1-8烷氧基-羰基、任选地被取代的C1-8烷氧基-草酰基、任选地被取代的C3-8环烷基-羰基、任选地被取代的C2-8链烯基-羰基或任选地被取代的苯甲酰基;R6是氢或卤素;R7是氢、卤素或C1-2烷基;n是0、1或2,条件是当R3是氰基、C1-4烷基-羰基或C1-4烷氧基-硫代羰基时,n是0;是反式或顺式单键;R8是任选地被取代的C1-8烷基、任选地被取代的C2-8链烯基、任选地被取代的苯基、任选地被取代的C3-8环烷基、任选地被取代的C1-8烷基-羰基或任选地被取代的C1-8烷氧基-羰基,或氢;R9是任选地被取代的C1-8烷基、任选地被取代的C3-8环烷基、任选地被取代的C2-8链烯基或任选地被取代的C3-8炔基;R10是氢或C1-4烷基;R11是氢、任选地被取代的C1-4烷基或任选地被取代的苯基;和Z是氧或硫。
本发明的式(I)化合物可按下述方法制得:
(a)当R5是氢时,
在惰性溶剂存在下,适当的话在酸催化剂存在下,使式(II)化合物
式中R4的定义同前;或者
(b)当R5是氢,R4是
,且R11不是氢,则R11由R12代替,R12是任选地被取代的C1-4烷基或任选地被取代的苯基时,
式中R1、R2、R3、R6、R7和n的定义同前,与式(V)化合物反应,
OCN-R12 (V)
式中R12是任选地被取代的C1-4烷基或任选地被取代的苯基;或者
(c)当R4是-CO-R8或-CO-OR9,条件是R8不是氢,则R8或-OR9由R13代替时,
在惰性溶剂存在下,适当的话在酸结合剂存在下,使上述的式(IV)化合物与式(VI)化合物反应
式中hal是氯或溴,和R13是R8或-OR9;或者
(d)当R5不是氢,则R5由R14代替时,
在惰性溶剂存在下,适当的话在酸结合剂存在下,使式(VII)化合物
式中R1、R2、R3、R4、R6、R7和n的定义同上,与式(VIII)化合物反应,
hal-R14 (VIII)
式中hal和R14的定义同上;或者
(e)当n是1时,
在惰性溶剂存在下,氧化式(IX)化合物
式中R1、R2、R3、R4、R5、R6和R7的定义同上;或者
(f)当n是2时,
在惰性溶剂存在下,氧化式(X)化合物
式中R1、R2、R3、R4、R5、R6和R7的定义同上,而q是0
或1。
本发明的式(I)的二苯酮腙衍生物显示出强有力的杀虫作用,特别是抗鳞翅目、鞘翅目和土壤昆虫。
按照本发明,式(I)的二苯酮腙衍生物与上述参考文献中描述的那些与本发明化合物相似的化合物相比较,出人意料地显示出明显优越的杀虫作用。
在本发明的式(I)化合物和代表用于制备式(I)化合物的各中间体的各个结构式的化合物中,每一个卤素及卤代烷基、卤代链烯基和卤代烷氧基的卤素部分指的是氟、氯、溴和碘,优选氟、氯或溴。
烷基代表例如甲基、乙基、丙基、异丙基、正-(异-、仲-或叔-)丁基、正-(异-、仲-、叔-或新-)戊基和正-(异-、仲-、叔-或新-)己基,优选甲基、乙基、丙基、异丙基和正-(异-、仲-或叔-)丁基。
链烯基代表例如乙烯基、烯丙基、异丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-(或3-)丁烯基、2-(3-或4-)戊烯基。
炔基代表例如炔丙基。
苯基和苯氧基可以任选地被一个或多个取代基取代,所述取代基选自卤素(氟、氯、溴)、氰基、硝基、烷基(甲基、乙基、丙基或异丙基)、卤代烷基(三氟甲基)、烷氧基(甲氧基、乙氧基)、卤代烷氧基(三氟甲氧基)和烷硫基(甲硫基)。
环烷基代表例如环丙基、环丁基、环戊基、环己基、环庚基和环辛基。环烷基可任选地被C1-4烷基(甲基、乙基、丙基、异丙基和丁基)取代。
烷氧基代表例如甲氧基、乙氧基、丙氧基、异丙氧基、正-(异-、仲-或叔-)丁氧基、正-(异-、仲-、叔-或新-)戊氧基、正-(异-、仲-、叔-或新-)己氧基。
卤代烷氧基代表被相同或不同的卤原子取代的上述烷氧基,例如三氟甲氧基。
烷硫基代表例如甲硫基、乙硫基、丙硫基、异丙硫基、正-(异-、仲-或叔-)丁硫基、正-(异-、仲-、叔-或新-)戊硫基、正-(异-、仲-、叔-或新-)己硫基。
在本发明式(I)的二苯酮腙衍生物中,优选的化合物是这样的化合物,其中R1是卤素;R2是氢或C1-3烷基R3是氰基;C1-4烷基,该烷基可被选自卤素、氰基、甲氧基、乙氧基和三甲基甲硅烷基的一个或多个取代基取代;或者是C2-3链烯基、炔丙基、甲基-羰基、甲氧基-硫代羰基或乙氧基-硫代羰基;R4是氢、C1-4烷基、C2-4链烯基、苯基,或是苄基、-CO-R8、-CO-OR9或
;R5是氢;甲酰基;苯基;可被选自卤素、氰基、C1-4烷氧基、C1-4烷硫基、羟基羰基、C1-4烷氧基羰基、苯基、被卤素取代的苯基和甲氧基苯基的一个或多个取代基取代的C1-6烷基;C2-6链烯基;C3-6炔基;C1-6烷基-羰基;C1-6卤代烷基-羰基;C1-4烷氧基-C1-6烷基-羰基;C1-6烷基-草酰基;可被选自C3-6环烷基和C1-4烷氧基的一个或多个取代基取代的C1-6烷氧基-羰基;C1-6烷氧基-草酰基;可被C1-4烷基取代的C3-6环烷基-羰基;可被苯基取代的C2-6链烯基-羰基;或苯甲酰基,它可被选自卤素、硝基、氰基、C1-4烷氧基和C1-4烷硫基的一个或多个取代基取代;R6是氢或卤素;R7是氢或卤素或C1-2烷基;n是0、1或2,条件是当R3是氰基、甲基-羰基、甲氧基-硫代羰基或乙氧基-硫代羰基时,n是0;是反式或顺式单键;R8是可被选自卤素、氰基、C1-4烷氧基、C1-4烷氧基-羰基和苯氧基的一个或多个取代基取代的C1-6烷基;可被选自卤素和苯基的一个 或多个取代基取代的C2-6链烯基;可被选自卤素、硝基、氰基、C1-4烷基、C1-4烷氧基和C1-4烷硫基的一个或多个取代基取代的苯基;可被C1-4烷基取代的C3-6环烷基;或者C1-6烷基-羰基;C1-6烷氧基-羰基;或氢;R9是可被选自卤素、苯基、4-硝基苯基、三甲基甲硅烷基和C3-6环烷基的一个或多个取代基取代的C1-6烷基;C3-6环烷基;可被苯基取代的C2-6链烯基;或C3-6炔基;R10是氢或C1-4烷基;R11是氢;可被卤素取代的C1-4烷基;或可被选自卤素、C1-4烷氧基或C1-4卤代烷氧基的一个或多个取代基取代的苯基;和Z是氧或硫。
特别优选的式(I)的二苯酮腙衍生物是下述化合物,其中R1是氟、氯、溴或碘;R2是氢、甲基、乙基或正丙基;R3是氰基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、氰基甲基、氟甲基、氯甲基、二氟甲基、三氟甲基、2-氟乙基、2-氯乙基、2,2-二氟乙基、2,2,2-三氟乙基、3-氟丙基、3-氯丙基、2,2,3,3-四氟丙基、甲氧基甲基、乙氧基甲基、三甲基甲硅烷基甲基、乙烯基、烯丙基、炔丙基、甲基-羰基或乙氧基-硫代羰基;R4是氢、甲基、乙基、丙基、异丙基、正丁基、叔丁基、烯丙基、苯基、苄基、-CO-R8、-CO-OR9或
;R5是氢、甲基、乙基、丙基、异丙基、正丁基、叔丁基、正戊基、正己基、甲氧基甲基、乙氧基甲基、甲硫基甲基、甲硫基乙基、甲氧羰基甲基、乙氧羰基甲基、2-乙氧羰基乙基、二氟甲基、2-氯乙 基、2,2-二氟乙基、2,2,2-三氟乙基、氰基甲基、氰基乙基、乙烯基、烯丙基、炔丙基、苯基、苯甲酰基、肉桂酰基、苄基、4-氯苯甲酰基、4-甲氧基苯甲酰基、甲酰基、甲基羰基、乙基羰基、丙基羰基、异丙基羰基、正丁基羰基、2,2,2-三氟乙基羰基、5-溴戊基羰基、甲氧甲基羰基、甲基草酰基、乙基草酰基、丙基草酰基、异丙基草酰基、正丁基草酰基、甲氧羰基、乙氧羰基、丙氧羰基、丁氧羰基、甲氧草酰基、乙氧草酰基、丙氧草酰基、丁氧草酰基、环丙基羰基、1-甲基环丙基羰基、环丙基甲氧基羰基、2-甲氧基乙氧羰基或羟基羰基乙基;R6是氢、氟或氯;R7是氢、溴或甲基;n是0、1或2,条件是当R3是甲基-羰基或乙氧基-硫代羰基时n为0;是反式或顺式单键;R8是甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基、氰基甲基、2-氯乙基、3-氯丙基、4-氯丁基、甲氧甲基、2-甲氧乙基、苯氧甲基、乙氧羰基甲基、乙烯基、异丙烯基、1-丙烯基、2,3,3-三氟-2-丙烯基、苯基、4-氯苯基、4-溴苯基、4-甲基苯基、4-甲氧基苯基、苯乙烯基、环丙基、环戊基、环己基、1-甲基环丙基、甲基羰基、乙基羰基、丙基羰基、甲氧羰基、乙氧羰基、丙氧羰基或氢;R9是甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、新戊基、2-甲基丁基、正己基、三甲基甲硅烷基甲基、烯丙基、环戊基、环己基、2-甲基-2-丙烯基、炔丙基、2-氯乙基、2,2,2-三氟乙基、2,2,3,3-四氟丙基、环丙基甲基、环己基甲基、苄基或4-硝基苄基;R10是氢或甲基;R11是氢、甲基、乙基、2-氯乙基、苯基、2-氯苯基、2-甲氧基苯基或4-三氟甲氧基苯基;和Z是氧或硫。
具体提及的本发明化合物是下述表1至表4中的化合物。
表1
R1 R2 R3 n R5 R6 R7 R9F H CH3 0 H H H CH3F H CH3 0 H H H C2H5F H CH3 0 H 3-F H CH3F H CH3 0 H 3-F H C2H5F H CH3 1 H H H CH3F H CH3 1 H H H C2H5F H CH3 1 H H H n-C3H7F H CH3 1 H H H i-C3H7F H CH3 1 H H H i-C4H9F H CH3 1 H H H CH2CF3F H CH3 2 H H H C2H5F H CH3 2 H H H n-C3H7F H CH3 2 H H H i-C3H7F H CH3 2 H H H i-C4H9F H CH3 2 H H H CH2CF3F H C2H5 0 H H H C2H5F H C2H5 0 H 3-F H C2H5F H C2H5 1 H H H CH3F H C2H5 1 H H H C2H5F H C2H5 1 H H H CH2CF3F H C2H5 1 H H H i-C3H7F H C2H5 2 H H H CH3F H C2H5 2 H H H C2H5F H C2H5 2 H H H n-C3H7F H C2H5 2 H H H i-C4H9F H C2H5 2 H H H CH2CF3F H C2H5 2 H 3-F H C2H5F H CH2CH2F 0 H H H CH3F H CH2CF3 0 H H H CH3F H CH2CF3 0 H 3-F H CH3Cl H CH3 0 H H H CH3
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 0 H H H C2H5Cl H CH3 0 H H H n-C3H7Cl H CH3 0 H H H i-C3H7Cl H CH3 0 H H H s-C4H9Cl H CH3 0 H H H t-C4H9Cl H CH3 0 H H H n-C4H9Cl H CH3 0 H H H i-C4H9Cl H CH3 0 H H H n-C5H11Cl H CH3 0 H H H n-C5H11Cl H CH3 0 H H H CH2CH(CH3)C2H5Cl H CH3 0 H H H n-C6H13Cl H CH3 0 H H H n-C7H15Cl H CH3 0 H H H n-C8H17Cl H CH3 0 H H H CH2CH=CH2Cl H CH3 0 H H H CH2C(CH3)=CH2Cl H CH3 0 H H H CH2C≡CHCl H CH3 0 H H H CH2C6H5Cl H CH3 0 H H H CH2CF3Cl H CH3 0 H H H CH2CH2ClCl H CH3 0 H H H CH2CH2OCH3Cl H CH3 0 H H H CH2Si(CH3)3Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H 2-F C2H5Cl H CH3 0 H H 3-F C2H5Cl H CH3 0 H H 3-Cl C2H5Cl H CH3 0 H H 3-Br C2H5Cl H CH3 0 H H 3-CH3 C2H5Cl H CH3 0 H 2-F H CH3Cl H CH3 0 H 2-F H C2H5Cl H CH3 0 H 2-Cl H CH3Cl H CH3 0 H 2-Cl H C2H5Cl H CH3 0 H 3-F H CH3Cl H CH3 0 H 3-F H C2H5Cl H CH3 0 H 3-Cl H CH3
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 0 H 3-Cl H C2H5Cl H CH3 0 CH3 H H CH3Cl H CH3 0 CH3 H H C2H5Cl H CH3 0 CH3 H H n-C3H7Cl H CH3 0 CH3 H H i-C3H7Cl H CH3 0 CH3 H H CH2CF3Cl H CH3 0 C2H5 H H CH3Cl H CH3 0 C2H5 H H C2H5Cl H CH3 0 C2H5 H H n-C3H7Cl H CH3 0 C2H5 H H i-C3H7Cl H CH3 0 C2H5 H H n-C4H9Cl H CH3 0 C2H5 H H i-C4H9Cl H CH3 0 C2H5 H H s-C4H9Cl H CH3 0 C2H5 H H CH2CF3Cl H CH3 0 n-C3H7 H H CH3Cl H CH3 0 n-C3H7 H H C2H5Cl H CH3 0 n-C3H7 H H n-C3H7Cl H CH3 0 n-C3H7 H H i-C3H7Cl H CH3 0 n-C3H7 H H CH2CF3Cl H CH3 0 i-C3H7 H H CH3Cl H CH3 0 i-C3H7 H H C2H5Cl H CH3 0 i-C3H7 H H n-C3H7Cl H CH3 0 i-C3H7 H H i-C3H7Cl H CH3 0 i-C3H7 H H n-C4H9Cl H CH3 0 i-C3H7 H H i-C4H9Cl H CH3 0 i-C3H7 H H s-C4H9Cl H CH3 0 i-C3H7 H H CH2CF3Cl H CH3 0 n-C4H9 H H CH3Cl H CH3 0 n-C4H9 H H C2H5Cl H CH3 0 n-C4H9 H H n-C3H7Cl H CH3 0 n-C4H9 H H i-C3H7Cl H CH3 0 CHF2 H H C2H5Cl H CH3 0 CH2OCH3 H H CH3Cl H CH3 0 CH2OCH3 H H C2H5Cl H CH3 0 CH2OCH3 H H n-C3H7Cl H CH3 0 CH2OCH3 H H i-C3H7Cl H CH3 0 CH2OCH3 H H CH2CF3Cl H CH3 0 CH2OC2H5 H H CH3Cl H CH3 0 CH2OC2H5 H H C2H5Cl H CH3 0 CH2OC2H5 H H n-C3H7Cl H CH3 0 CH2OC2H5 H H i-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 0 CH2OC2H5 H H CH2CF3Cl H CH3 0 CH2SCH3 H H CH3Cl H CH3 0 CH2SCH3 H H C2H5Cl H CH3 0 CH2SCH3 H H n-C3H7Cl H CH3 0 CH2SCH3 H H i-C3H7Cl H CH3 0 CH2SCH3 H H CH2CF3Cl H CH3 0 CH2C6H5 H H C2H5Cl H CH3 0 CH2CO2C2H5 H H C2H5Cl H CH3 0 CH2CH2CO2C2H5 H H C2H5Cl H CH3 0 CHO H H CH3Cl H CH3 0 CHO H H C2H5Cl H CH3 0 COCH3 H H CH3Cl H CH3 0 COCH3 H H C2H5Cl H CH3 0 COCH3 H H n-C3H7Cl H CH3 0 COCH3 H H i-C3H7Cl H CH3 0 COC2H5 H H CH3Cl H CH3 0 COC2H5 H H C2H5Cl H CH3 0 COC2H5 H H n-C3H7Cl H CH3 0 COC2H5 H H i-C3H7Cl H CH3 0 COC2H5 H H CH2CF3Cl H CH3 0 COC3H7-n H H CH3Cl H CH3 0 COC3H7-n H H C2H5Cl H CH3 0 COC3H7-n H H n-C3H7Cl H CH3 0 COC3H7-n H H i-C3H7Cl H CH3 0 COC3H7-n H H n-C4H9Cl H CH3 0 COC3H7-n H H s-C4H9Cl H CH3 0 COC3H7-n H H i-C4H9Cl H CH3 0 COC3H7-n H H CH2CF3Cl H CH3 0 COC3H7-i H H CH3Cl H CH3 0 COC3H7-i H H C2H5Cl H CH3 0 COC3H7-i H H n-C3H7Cl H CH3 0 COC4H9-n H H CH3Cl H CH3 0 COC4H9-n H H C2H5Cl H CH3 0 COC4H9-n H H n-C3H7Cl H CH3 0 COC4H9-n H H i-C3H7Cl H CH3 0
H H CH3Cl H CH3 0
H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 0
H H n-C3H7Cl H CH3 0
H H C2H5Cl H CH3 0 COC6H5 H H CH3Cl H CH3 0 COC6H5 H H C2H5Cl H CH3 0 COC6H5 H H n-C3H7Cl H CH3 0 COC6H5 H H i-C3H7Cl H CH3 0 COC6H5 H H CH2CF3Cl H CH3 0
H H C2H5Cl H CH3 0
H H C2H5Cl H CH3 0 COCH=CHC6H5 H H C2H5Cl H CH3 0 COCH2OCH3 H H CH3Cl H CH3 0 COCH2OCH3 H H C2H5Cl H CH3 0 COCH2OCH3 H H n-C3H7Cl H CH3 1 H H H CH3Cl H CH3 1 H H H C2H5Cl H CH3 1 H H H n-C3H7Cl H CH3 1 H H H i-C3H7Cl H CH3 1 H H H CH2CF3Cl H CH3 1 H H H i-C4H9Cl H CH3 1 H H H t-C4H9Cl H CH3 1 H 2-Cl H C2H5Cl H CH3 1 H 2-F H C2H5Cl H CH3 1 H 3-F H C2H5Cl H CH3 1 H 3-Cl H C2H5Cl H CH3 1 CH3 H H C2H5Cl H CH3 1 C2H5 H H C2H5Cl H CH3 1 C2H5 H H CH2CF3Cl H CH3 1 C2H5 H H n-C3H7Cl H CH3 1 C2H5 H H n-C4H9Cl H CH3 1 C2H5 H H s-C4H9Cl H CH3 1 C2H5 H H i-C4H9Cl H CH3 1 C2H5 H H CH3Cl H CH3 1 C2H5 H H i-C3H7Cl H CH3 1 i-C3H7 H H CH3Cl H CH3 1 i-C3H7 H H C2H5Cl H CH3 1 i-C3H7 H H n-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 1 i-C3H7 H H i-C3H7Cl H CH3 1 CH2OCH3 H H CH3Cl H CH3 1 CH2OCH3 H H C2H5Cl H CH3 1 CH2OC2H5 H H CH3Cl H CH3 1 CH2OC2H5 H H C2H5Cl H CH3 1 CH2SCH3 H H CH3Cl H CH3 1 CH2SCH3 H H C2H5Cl H CH3 1 COCH3 H H C2H5Cl H CH3 1 COC2H5 H H CH3Cl H CH3 1 COC2H5 H H C2H5Cl H CH3 1 COC2H5 H H n-C3H7Cl H CH3 1 COC2H5 H H i-C3H7Cl H CH3 1 COC3H7-n H H CH3Cl H CH3 1 COC3H7-n H H C2H5Cl H CH3 1 COC3H7-n H H n-C3H7Cl H CH3 1 COC3H7-n H H i-C3H7Cl H CH3 1 COC3H7-i H H CH3Cl H CH3 1 COC3H7-i H H C2H5Cl H CH3 1 COC3H7-i H H n-C3H7Cl H CH3 1 COC3H7-i H H i-C3H7Cl H CH3 1
H H CH3Cl H CH3 1
H H n-C3H7Cl H CH3 1
H H i-C3H7Cl H CH3 1
H H C2H5Cl H CH3 1 COC6H5 H H CH3Cl H CH3 1 COC6H5 H H C2H5Cl H CH3 1 COC6H5 H H n-C3H7Cl H CH3 1 COC6H5 H H i-C3H7Cl H CH3 1 COCH2OCH3 H H CH3Cl H CH3 1 COCH2OCH3 H H C2H5Cl H CH3 1 COCH2OCH3 H H n-C3H7Cl H CH3 2 H H H CH3Cl H CH3 2 H H H C2H5Cl H CH3 2 H H H CH2CF3Cl H CH3 2 H H H n-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 2 H H H i-C3H7Cl H CH3 2 H H H i-C4H9Cl H CH3 2 H H H s-C4H9Cl H CH3 2 H H H t-C4H9Cl H CH3 2 CH3 H H C2H5Cl H CH3 2 C2H5 H H CH3Cl H CH3 2 C2H5 H H C2H5Cl H CH3 2 C2H5 H H n-C3H7Cl H CH3 2 C2H5 H H i-C3H7Cl H CH3 2 C2H5 H H n-C4H9Cl H CH3 2 C2H5 H H i-C4H9Cl H CH3 2 C2H5 H H s-C4H9Cl H CH3 2 C2H5 H H CH2CF3Cl H CH3 2 i-C3H7 H H CH3Cl H CH3 2 i-C3H7 H H C2H5Cl H CH3 2 i-C3H7 H H n-C3H7Cl H CH3 2 i-C3H7 H H i-C3H7Cl H CH3 2 CH2OCH3 H H CH3Cl H CH3 2 CH2OCH3 H H C2H5Cl H CH3 2 CH2OC2H5 H H CH3Cl H CH3 2 CH2OC2H5 H H C2H5Cl H CH3 2 CH2SCH3 H H CH3Cl H CH3 2 CH2SCH3 H H C2H5Cl H CH3 2 COCH3 H H C2H5Cl H CH3 2 COC2H5 H H CH3Cl H CH3 2 COC2H5 H H C2H5Cl H CH3 2 COC2H5 H H n-C3H7Cl H CH3 2 COC2H5 H H i-C3H7Cl H CH3 2 COC3H7-n H H C2H5Cl H CH3 2 COC3H7-n H H n-C3H7Cl H CH3 2 COC3H7-n H H i-C3H7Cl H CH3 2 COC3H7-n H H CH3Cl H CH3 2 COC3H7-i H H CH3Cl H CH3 2 COC3H7-i H H C2H5Cl H CH3 2 COC3H7-i H H n-C3H7Cl H CH3 2 COC3H7-i H H i-C3H7Cl H CH3 2
H H CH3
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 2
H H C2H5Cl H CH3 2
H H n-C3H7Cl H CH3 2
H H i-C3H7Cl H CH3 2 COC6H5 H H CH3Cl H CH3 2 COC6H5 H H C2H5Cl H CH3 2 COC6H5 H H n-C3H7Cl H CH3 2 COC6H5 H H i-C3H7Cl H CH3 2 COCH2OCH3 H H CH3Cl H CH3 2 COCH2OCH3 H H C2H5Cl H CH3 2 COCH2OCH3 H H n-C3H7Cl H C2H5 0 H H H CH3Cl H C2H5 0 H H H C2H5Cl H C2H5 0 H H H i-C3H7Cl H C2H5 0 H H H i-C4H9Cl H C2H5 0 H H H n-C3H7Cl H C2H5 0 H H H n-C4H9Cl H C2H5 0 H H H s-C4H9Cl H C2H5 0 H H H n-C5H11Cl H C2H5 0 H H H CH2CF3Cl H C2H5 0 H H H CH2Si(CH3)3Cl H C2H5 0 H 2-F H C2H5Cl H C2H5 0 H 3-F H C2H5Cl H C2H5 0 H 2-Cl H C2H5Cl H C2H5 0 H 3-Cl H C2H5Cl H C2H5 0 CH3 H H CH3Cl H C2H5 0 CH3 H H C2H5Cl H C2H5 0 CH3 H H n-C3H7Cl H C2H5 0 CH3 H H i-C3H7Cl H C2H5 0 C2H5 H H CH3Cl H C2H5 0 C2H5 H H C2H5Cl H C2H5 0 C2H5 H H n-C3H7Cl H C2H5 0 C2H5 H H i-C3H7Cl H C2H5 0 C2H5 H H n-C4H9Cl H C2H5 0 C2H5 H H i-C4H9Cl H C2H5 0 C2H5 H H s-C4H9Cl H C2H5 0 C2H5 H H CH2CF3
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H C2H5 0 n-C3H7 H H CH3Cl H C2H5 0 n-C3H7 H H C2H5Cl H C2H5 0 n-C3H7 H H n-C3H7Cl H C2H5 0 n-C3H7 H H i-C3H7Cl H C2H5 0 i-C3H7 H H CH3Cl H C2H5 0 i-C3H7 H H C2H5Cl H C2H5 0 i-C3H7 H H n-C3H7Cl H C2H5 0 i-C3H7 H H i-C3H7Cl H C2H5 0 i-C3H7 H H n-C4H9Cl H C2H5 0 i-C3H7 H H i-C4H9Cl H C2H5 0 i-C3H7 H H s-C4H9Cl H C2H5 0 i-C3H7 H H CH2CF3Cl H C2H5 0 n-C4H9 H H CH3Cl H C2H5 0 n-C4H9 H H C2H5Cl H C2H5 0 n-C4H9 H H n-C3H7Cl H C2H5 0 n-C4H9 H H i-C3H7Cl H C2H5 0 CH2OCH3 H H CH3Cl H C2H5 0 CH2OCH3 H H C2H5Cl H C2H5 0 CH2OCH3 H H n-C3H7Cl H C2H5 0 CH2OCH3 H H i-C3H7Cl H C2H5 0 CH2OCH3 H H CH2CF3Cl H C2H5 0 CH2OC2H5 H H CH3Cl H C2H5 0 CH2OC2H5 H H C2H5Cl H C2H5 0 CH2OC2H5 H H n-C3H7Cl H C2H5 0 CH2OC2H5 H H i-C3H7Cl H C2H5 0 CH2OC2H5 H H CH2CF3Cl H C2H5 0 CH2SCH3 H H CH3Cl H C2H5 0 CH2SCH3 H H C2H5Cl H C2H5 0 CH2SCH3 H H n-C3H7Cl H C2H5 0 CH2SCH3 H H i-C3H7Cl H C2H5 0 CH2SCH3 H H CH2CF3Cl H C2H5 0 CHO H H C2H5Cl H C2H5 0 COCH3 H H CH3Cl H C2H5 0 COCH3 H H C2H5Cl H C2H5 0 COCH3 H H n-C3H7Cl H C2H5 0 COC2H5 H H CH3Cl H C2H5 0 COC2H5 H H C2H5Cl H C2H5 0 COC2H5 H H n-C3H7Cl H C2H5 0 COC2H5 H H i-C3H7Cl H C2H5 0 COC2H5 H H CH2CF3Cl H C2H5 0 COC3H7-n H H CH3
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H C2H5 0 COC3H7-n H H C2H5Cl H C2H5 0 COC3H7-n H H n-C3H7Cl H C2H5 0 COC3H7-n H H i-C3H7Cl H C2H5 0 COC3H7-n H H n-C4H9Cl H C2H5 0 COC3H7-n H H i-C4H9Cl H C2H5 0 COC3H7-n H H s-C4H9Cl H C2H5 0 COC3H7-n H H CH2CF3Cl H C2H5 0 COC3H7-i H H CH3Cl H C2H5 0 COC3H7-i H H C2H5Cl H C2H5 0 COC3H7-i H H n-C3H7Cl H C2H5 0 COC4H9-n H H CH3Cl H C2H5 0 COC4H9-n H H C2H5Cl H C2H5 0 COC4H9-n H H n-C3H7Cl H C2H5 0 COC4H9-n H H i-C3H7Cl H C2H5 0 COCH2OCH3 H H CH3Cl H C2H5 0 COCH2OCH3 H H C2H5Cl H C2H5 0 COCH2OCH3 H H n-C3H7Cl H C2H5 0
H H CH3Cl H C2H5 0
H H C2H5Cl H C2H5 0
H H n-C3H7Cl H C2H5 0 COC6H5 H H CH3Cl H C2H5 0 COC6H5 H H C2H5Cl H C2H5 0 COC6H5 H H n-C3H7Cl H C2H5 0 COC6H5 H H i-C3H7Cl H C2H5 0 COC6H5 H H CH2CF3Cl H C2H5 0
H H C2H5Cl H C2H5 1 H H H CH3Cl H C2H5 1 H H H C2H5Cl H C2H5 1 H H H n-C3H7Cl H C2H5 1 H H H i-C3H7Cl H C2H5 1 H H H i-C4H9Cl H C2H5 1 H H H CH2CF3
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H C2H5 1 C2H5 H H CH3Cl H C2H5 1 C2H5 H H C2H5Cl H C2H5 1 C2H5 H H n-C3H7Cl H C2H5 1 C2H5 H H i-C3H7Cl H C2H5 1 C2H5 H H n-C4H9Cl H C2H5 1 C2H5 H H i-C4H9Cl H C2H5 1 C2H5 H H s-C4H9Cl H C2H5 1 C2H5 H H CH2CF3Cl H C2H5 1 i-C3H7 H H CH3Cl H C2H5 1 i-C3H7 H H C2H5Cl H C2H5 1 i-C3H7 H H n-C3H7Cl H C2H5 1 i-C3H7 H H i-C3H7Cl H C2H5 1 CH2OCH3 H H CH3Cl H C2H5 1 CH2OC2H5 H H CH3Cl H C2H5 1 CH2OC2H5 H H C2H5Cl H C2H5 1 CH2SCH3 H H CH3Cl H C2H5 1 CH2SCH3 H H C2H5Cl H C2H5 1 COC2H5 H H CH3Cl H C2H5 1 COC2H5 H H C2H5Cl H C2H5 1 COC2H5 H H n-C3H7Cl H C2H5 1 COC2H5 H H i-C3H7Cl H C2H5 1 COC3H7-n H H CH3Cl H C2H5 1 COC3H7-n H H C2H5Cl H C2H5 1 COC3H7-n H H n-C3H7Cl H C2H5 1 COC3H7-n H H i-C3H7Cl H C2H5 1 COC3H7-i H H CH3Cl H C2H5 1 COC3H7-i H H C2H5Cl H C2H5 1 COC3H7-i H H n-C3H7Cl H C2H5 1 COC3H7-i H H i-C3H7Cl H C2H5 1
H H CH3Cl H C2H5 1
H H C2H5Cl H C2H5 1
H H n-C3H7Cl H C2H5 1
H H i-C3H7Cl H C2H5 1 COCH2OCH3 H H CH3Cl H C2H5 1 COCH2OCH3 H H C2H5
表1(续)R1R2 R3 n R5 R6 R7 R9Cl H C2H5 1 COCH2OCH3 H H n-C3H7Cl H C2H5 1 COC6H5 H H CH3Cl H C2H5 1 COC6H5 H H C2H5Cl H C2H5 1 COC6H5 H H n-C3H7Cl H C2H5 1 COC6H5 H H i-C3H7Cl H C2H5 2 H H H CH3Cl H C2H5 2 H H H C2H5Cl H C2H5 2 H H H n-C3H7Cl H C2H5 2 H H H i-C3H7Cl H C2H5 2 H H H i-C4H9Cl H C2H5 2 H H H CH2CF3Cl H C2H5 2 H 2-F H C2H5Cl H C2H5 2 H 3-F H C2H5Cl H C2H5 2 H 2-Cl H C2H5Cl H C2H5 2 H 3-Cl H C2H5Cl H C2H5 2 C2H5 H H CH3Cl H C2H5 2 C2H5 H H C2H5Cl H C2H5 2 C2H5 H H n-C3H7Cl H C2H5 2 C2H5 H H i-C3H7Cl H C2H5 2 C2H5 H H n-C4H9Cl H C2H5 2 C2H5 H H s-C4H9Cl H C2H5 2 C2H5 H H i-C4H9Cl H C2H5 2 C2H5 H H CH2CF3Cl H C2H5 2 i-C3H7 H H CH3Cl H C2H5 2 i-C3H7 H H C2H5Cl H C2H5 2 i-C3H7 H H n-C3H7Cl H C2H5 2 i-C3H7 H H i-C3H7Cl H C2H5 2 CH2OCH3 H H CH3Cl H C2H5 2 CH2OCH3 H H C2H5Cl H C2H5 2 CH2OC2H5 H H CH3Cl H C2H5 2 CH2OC2H5 H H C2H5Cl H C2H5 2 CH2SCH3 H H CH3Cl H C2H5 2 CH2SCH3 H H C2H5Cl H C2H5 2 CHO H H C2H5Cl H C2H5 2 COC2H5 H H CH3Cl H C2H5 2 COC2H5 H H C2H5Cl H C2H5 2 COC2H5 H H n-C3H7Cl H C2H5 2 COC2H5 H H i-C3H7Cl H C2H5 2 COC3H7-n H H CH3Cl H C2H5 2 COC3H7-n H H C2H5Cl H C2H5 2 COC3H7-n H H n-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H C2H5 2 COC3H7-n H H i-C3H7Cl H C2H5 2 COC3H7-i H H CH3Cl H C2H5 2 COC3H7-i H H C2H5Cl H C2H5 2 COC3H7-i H H n-C3H7Cl H C2H5 2 COC3H7-i H H i-C3H7Cl H C2H5 2
H H CH3Cl H C2H5 2
H H C2H5Cl H C2H5 2
H H n-C3H7Cl H C2H5 2
H H i-C3H7Cl H C2H5 2 COC6H5 H H CH3Cl H C2H5 2 COC6H5 H H C2H5Cl H C2H5 2 COC6H5 H H n-C3H7Cl H C2H5 2 COCH2OCH3 H H CH3Cl H C2H5 2 COCH2OCH3 H H C2H5Cl H C2H5 2 COCH2OCH3 H H n-C3H7Cl H n-C3H7 0 H H H CH3Cl H n-C3H7 0 H H H C2H5Cl H n-C3H7 0 H H H n-C3H7Cl H n-C3H7 0 H H H i-C4H9Cl H n-C3H7 0 C2H5 H H CH3Cl H n-C3H7 0 C2H5 H H C2H5Cl H n-C3H7 0 i-C3H7 H H C2H5Cl H n-C3H7 0 COC3H7-n H H C2H5Cl H n-C3H7 1 H H H CH3Cl H n-C3H7 1 H H H C2H5Cl H n-C3H7 1 H H H n-C3H7Cl H n-C3H7 1 H H H i-C3H7Cl H n-C3H7 1 H H H i-C4H9Cl H n-C3H7 1 H H H CH2CF3Cl H n-C3H7 2 H H H CH3Cl H n-C3H7 2 H H H C2H5Cl H n-C3H7 2 H H H CH2CF3Cl H n-C3H7 2 H H H n-C3H7Cl H n-C3H7 2 H H H i-C3H7Cl H n-C3H7 2 H H H i-C4H9Cl H i-C3H7 0 H H H CH3
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H i-C3H7 0 H H H C2H5Cl H i-C3H7 1 H H H CH3Cl H i-C3H7 1 H H H C2H5Cl H i-C3H7 2 H H H CH3Cl H i-C3H7 2 H H H C2H5Cl H n-C4H9 0 H H H C2H5Cl H S-C4H9 0 H H H C2H5Cl H CH2OCH3 0 H H H CH3Cl H CH2OCH3 0 H H H C2H5Cl H CH2OC2H5 0 H H H C2H5Cl H CH2Si(CH3)3 0 H H H C2H5Cl H CH2F 0 H H H C2H5Cl H CH2F 1 H H H CH3Cl H CH2F 1 H H H C2H5Cl H CH2F 1 H H H n-C3H7Cl H CH2F 1 H H H i-C3H7Cl H CH2F 1 H H H i-C4H9Cl H CH2F 1 H H H CH2CF3Cl H CHF2 0 H H H CH3Cl H CHF2 0 H H H C2H5Cl H CHF2 0 H H H i-C3H7Cl H CHF2 0 H H H i-C4H9Cl H CHF2 0 H H H n-C4H9Cl H CHF2 0 H H H n-C5H11Cl H CHF2 0 H H H n-C6H13Cl H CHF2 0 H H H CH2CF3Cl H CHF2 0 C2H5 H H CH3Cl H CHF2 0 C2H5 H H C2H5Cl H CHF2 0 i-C3H7 H H CH3Cl H CHF2 0 i-C3H7 H H C2H5Cl H CHF2 0 COC3H7-n H H C2H5Cl H CHF2 1 H H H CH3Cl H CHF2 1 H H H C2H5Cl H CHF2 1 H H H CH2CF3Cl H CHF2 1 H H H n-C3H7Cl H CHF2 1 H H H i-C3H7Cl H CHF2 1 H H H i-C4H9Cl H CF3 0 H H H CH3Cl H CF3 0 H H H C2H5Cl H CF3 0 H H H CH2CF3Cl H CF3 0 H H H i-C4H9
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CF3 0 H H H n-C4H9Cl H CF3 0 H H H n-C5H11Cl H CF3 0 H H H n-C6H13Cl H CH2Cl 0 H H H C2H5Cl H CH2CH2F 0 H H H C2H5Cl H CH2CH2F 0 H H H CH2CF3Cl H CH2CH2F 0 H H H CH3Cl H CH2CH2F 0 H H H i-C4H9Cl H CH2CH2F 0 H H H n-C3H7Cl H CH2CH2F 1 H H H CH3Cl H CH2CH2F 1 H H H C2H5Cl H CH2CH2F 1 H H H n-C3H7Cl H CH2CH2F 1 H H H i-C3H7Cl H CH2CH2F 1 H H H i-C4H9Cl H CH2CH2F 1 H H H CH2CF3Cl H CH2CH2F 2 H H H CH3Cl H CH2CH2F 2 H H H C2H5Cl H CH2CH2F 2 H H H CH2CF3Cl H CH2CH2F 2 H H H n-C3H7Cl H CH2CH2F 2 H H H i-C3H7Cl H CH2CH2F 2 H H H i-C4H9Cl H CH2CHF2 0 H H H CH3Cl H CH2CHF2 0 H H H C2H5Cl H CH2CHF2 0 H H H CH2CF3Cl H CH2CHF2 0 H H H C4H9Cl H CH2CHF2 0 H H H n-C3H7Cl H CH2CHF2 1 H H H CH3Cl H CH2CHF2 1 H H H C2H5Cl H CH2CHF2 1 H H H n-C3H7Cl H CH2CHF2 1 H H H i-C3H7Cl H CH2CHF2 1 H H H i-C4H9Cl H CH2CHF2 1 H H H CH2CF3Cl H CH2CHF2 2 H H H CH3Cl H CH2CHF2 2 H H H C2H5Cl H CH2CHF2 2 H H H CH2CF3Cl H CH2CHF2 2 H H H n-C3H7Cl H CH2CHF2 2 H H H i-C3H7Cl H CH2CHF2 2 H H H i-C4H9Cl H CH2CF3 0 C2H5 H H C2H5Cl H CH2CF3 0 COC3H7-n H H C2H5Cl H CH2CF3 0 i-C3H7 H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH2CF3 0 H H H CH3Cl H CH2CF3 0 C2H5 H H CH3Cl H CH2CF3 0 H H H C2H5Cl H CH2CF3 0 H H H n-C4H9Cl H CH2CF3 0 H H H i-C4H9Cl H CH2CF3 0 H H H CH2CF3Cl H CH2CF3 1 H H H CH3Cl H CH2CF3 1 H H H C2H5Cl H CH2CF3 1 H H H CH2CF3Cl H CH2CF3 1 H H H n-C3H7Cl H CH2CF3 1 H H H i-C3H7Cl H CH2CF3 1 H H H i-C4H9Cl H CH2CF3 2 H H H CH3Cl H CH2CF3 2 H H H C2H5Cl H CH2CF3 2 H H H CH2CF3Cl H CH2CF3 2 H H H n-C3H7Cl H CH2CF3 2 H H H i-C3H7Cl H CH2CF3 2 H H H i-C4H9Cl H CH2CH2Cl 0 H H H C2H5Cl H CH2CH2Cl 2 H H H C2H5Cl H CH2CH2CH2F 0 H H H C2H5Cl H CH2CH2CH2F 2 H H H C2H5Cl H CH2CF2CF2H 0 H H H C2H5Cl H CF2CF2CF3 0 H H H C2H5Cl H CH2CH2CH2Cl 0 H H H C2H5Cl H CH=CH2 0 H H H CH3Cl H CH=CH2 0 H H H C2H5Cl H CH2CH=CH2 0 H H H C2H5Cl H CH2CH=CH2 1 H H H C2H5Cl H CH2CH=CH2 2 H H H C2H5Cl H CH2C≡CH 0 H H H C2H5Cl H CH2C≡CH 0 H H H CH3Cl H CH2C≡CH 1 H H H C2H5Cl H CH2C≡CH 2 H H H C2H5Cl H CH2CN 0 H H H CH3Cl H CH2CN 0 H H H C2H5Cl H CH2CN 1 H H H C2H5Cl H CH2CN 2 H H H C2H5Cl CH3 CH3 0 H H H CH3Cl CH3 CH3 0 H H H C2H5Cl CH3 CH3 0 H H H i-C4H9
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl CH3 CH3 0 H H H n-C4H9Cl CH3 CH3 0 H H H CH2CF3Cl CH3 CH3 1 H H H CH3Cl CH3 CH3 1 H H H C2H5Cl CH3 CH3 1 H H H i-C4H9Cl CH3 CH3 1 H H H CH2CF3Cl CH3 CH3 2 H H H CH3Cl CH3 CH3 2 H H H C3H5Cl CH3 CH3 2 H H H i-C4H9Cl CH3 CH3 2 H H H CH2CF3Cl C2H5 CH3 0 H H H CH3Cl C2H5 CH3 0 H H H C2H5Cl C2H5 CH3 1 H H H C2H5Cl C2H5 CH3 2 H H H C2H5Cl n-C3H7 CH3 0 H H H C2H5Br H CH3 0 H H H CH3Br H CH3 0 H H H C2H5Br H CH3 0 H H H n-C3H7Br H CH3 0 H H H i-C3H7Br H CH3 0 H H H n-C4H9Br H CH3 0 H H H s-C4H9Br H CH3 0 H H H i-C4H9Br H CH3 0 H H H t-C4H9Br H CH3 0 H H H n-C5H11Br H CH3 0 H H H n-C6H13Br H CH3 0 H H H CH2C≡CHBr H CH3 0 H H H CH2C6H5Br H CH3 0 H H H CH2CF3Br H CH3 0 CH3 H H CH3Br H CH3 0 CH3 H H C2H5Br H CH3 0 C2H5 H H CH3Br H CH3 0 C2H5 H H C2H5Br H CH3 0 C2H5 H H n-C3H7Br H CH3 0 C2H5 H H i-C3H7Br H CH3 0 C2H5 H H n-C4H9Br H CH3 0 C2H5 H H i-C4H9Br H CH3 0 C2H5 H H s-C4H9Br H CH3 0 C2H5 H H CH2CF3Br H CH3 0 i-C3H7 H H CH3Br H CH3 0 i-C3H7 H H C2H5Br H CH3 0 i-C3H7 H H n-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H CH3 0 i-C3H7 H H i-C3H7Br H CH3 0 i-C3H7 H H i-C4H9Br H CH3 0 i-C3H7 H H CH2CF3Br H CH3 0 CH2SCH3 H H CH3Br H CH3 0 CH2OCH3 H H CH3Br H CH3 0 CH2OCH3 H H C2H5Br H CH3 0 CH2OC2H5 H H C2H5Br H CH3 0 CH2SCH3 H H C2H5Br H CH3 0 CHO H H C2H5Br H CH3 0 COCH3 H H CH3Br H CH3 0 COCH3 H H C2H5Br H CH3 0 COC2H5 H H CH3Br H CH3 0 COC2H5 H H C2H5Br H CH3 0 COC2H5 H H n-C3H7Br H CH3 0 COC3H7-n H H CH3Br H CH3 0 COC3H7-n H H C2H5Br H CH3 0 COC3H7-n H H i-C3H7Br H CH3 0 COC3H7-n H H i-C4H9Br H CH3 0 COC3H7-n H H n-C3H7Br H CH3 0 COCH2OCH3 H H n-C3H7Br H CH3 0 COC6H5 H H CH3Br H CH3 0 COC6H5 H H C2H5Br H CH3 0
H H C2H5Br H CH3 0 COCH=CHC6H5 H H C2H5Br H CH3 0 COCH2OCH3 H H CH3Br H CH3 0 COCH2OCH3 H H C2H5Br H CH3 1 H H H CH3Br H CH3 1 H H H C2H5Br H CH3 1 H H H n-C3H7Br H CH3 1 H H H i-C3H7Br H CH3 1 H H H i-C4H9Br H CH3 1 H H H CH2CF3Br H CH3 1 C2H5 H H CH3Br H CH3 1 C2H5 H H C2H5Br H CH3 1 C2H5 H H n-C3H7Br H CH3 1 C2H5 H H i-C3H7Br H CH3 1 i-C3H7 H H CH3Br H CH3 1 i-C3H7 H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H CH3 1 i-C3H7 H H n-C3H7Br H CH3 1 i-C3H7 H H i-C3H7Br H CH3 1 COC2H5 H H CH3Br H CH3 1 COC2H5 H H C2H5Br H CH3 1 COC3H7-n H H CH3Br H CH3 1 COC3H7-n H H C2H5Br H CH3 1 COC2H5 H H n-C3H7Br H CH3 1 COC3H7-n H H n-C3H7Br H CH3 1 COCH2OCH3 H H n-C3H7Br H CH3 1 COCH2OCH3 H H C2H5Br H CH3 1 COCH2OCH3 H H CH3Br H CH3 1 COC3H7-n H H i-C3H7Br H CH3 2 H H H CH3Br H CH3 2 H H H C2H5Br H CH3 2 H H H i-C3H7Br H CH3 2 H H H i-C4H9Br H CH3 2 H H H n-C3H7Br H CH3 2 H H H CH2CF3Br H CH3 2 C2H5 H H CH3Br H CH3 2 C2H5 H H C2H5Br H CH3 2 C2H5 H H n-C3H7Br H CH3 2 C2H5 H H i-C3H7Br H CH3 2 i-C3H7 H H CH3Br H CH3 2 i-C3H7 H H C2H5Br H CH3 2 i-C3H7 H H n-C3H7Br H CH3 2 i-C3H7 H H i-C3H7Br H CH3 2 CH2OCH3 H H CH3Br H CH3 2 COC2H5 H H C2H5Br H CH3 2 COCH2OCH3 H H C2H5Br H CH3 2 COC2H5 H H CH3Br H CH3 2 COC2H5 H H n-C3H7Br H CH3 2 COC3H7-n H H CH3Br H CH3 2 COC3H7-n H H C2H5Br H CH3 2 COC3H7-n H H n-C3H7Br H CH3 2 COC3H7-n H H i-C3H7Br H CH3 2 COCH2OCH3 H H n-C3H7Br H CH3 2 COCH2OCH3 H H CH3Br H CH3 2 COC6H5 H H C2H5Br H C2H5 0 H H H CH3Br H C2H5 0 H H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H C2H5 0 H H H n-C3H7Br H C2H5 0 H H H i-C4H9Br H C2H5 0 H H H CH2CF3Br H C2H5 0 CH3 H H CH3Br H C2H5 0 CH3 H H C2H5Br H C2H5 0 C2H5 H H CH3Br H C2H5 0 C2H5 H H C2H5Br H C2H5 0 C2H5 H H n-C3H7Br H C2H5 0 C2H5 H H i-C3H7Br H C2H5 0 C2H5 H H n-C4H9Br H C2H5 0 C2H5 H H i-C4H9Br H C2H5 0 C2H5 H H s-C4H9Br H C2H5 0 C2H5 H H CH2CF3Br H C2H5 0 i-C3H7 H H CH3Br H C2H5 0 i-C3H7 H H C2H5Br H C2H5 0 i-C3H7 H H n-C3H7Br H C2H5 0 i-C3H7 H H i-C3H7Br H C2H5 0 i-C3H7 H H i-C4H9Br H C2H5 0 i-C3H7 H H CH2CF3Br H C2H5 0 CH2OCH3 H H CH3Br H C2H5 0 CH2OCH3 H H C2H5Br H C2H5 0 CH2SCH3 H H CH3Br H C2H5 0 CH2SCH3 H H C2H5Br H C2H5 0 CHO H H C2H5Br H C2H5 0 COCH3 H H C2H5Br H C2H5 0 COC2H5 H H CH3Br H C2H5 0 COC2H5 H H C2H5Br H C2H5 0 COC2H5 H H n-C3H7Br H C2H5 0 COC2H5 H H i-C3H7Br H C2H5 0 COC3H7-n H H CH3Br H C2H5 0 COC3H7-n H H C2H5Br H C2H5 0 COC3H7-n H H n-C3H7Br H C2H5 0 COC3H7-n H H i-C3H7Br H C2H5 0 COC3H7-n H H i-C4H9Br H C2H5 0 COCH2OCH3 H H CH3Br H C2H5 0 COCH2OCH3 H H C2H5Br H C2H5 0 COCH2OCH3 H H n-C3H7Br H C2H5 0 COC6H5 H H CH3Br H C2H5 0 COC6H5 H H C2H5Br H C2H5 1 H H H CH3Br H C2H5 1 H H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H C2H5 1 H H H n-C3H7Br H C2H5 1 H H H i-C3H7Br H C2H5 1 H H H i-C4H9Br H C2H5 1 H H H CH2CF3Br H C2H5 1 C2H5 H H CH3Br H C2H5 1 C2H5 H H C2H5Br H C2H5 1 C2H5 H H n-C3H7Br H C2H5 1 C2H5 H H i-C3H7Br H C2H5 1 i-C3H7 H H CH3Br H C2H5 1 i-C3H7 H H C2H5Br H C2H5 1 i-C3H7 H H n-C3H7Br H C2H5 1 COC2H5 H H CH3Br H C2H5 1 COC2H5 H H C2H5Br H C2H5 1 COC2H5 H H n-C3H7Br H C2H5 1 COC3H7-n H H CH3Br H C2H5 1 COC3H7-n H H C2H5Br H C2H5 1 COC3H7-n H H n-C3H7Br H C2H5 1 COC3H7-n H H i-C3H7Br H C2H5 1 i-C3H7 H H i-C3H7Br H C2H5 1 COCH2OCH3 H H CH3Br H C2H5 1 COCH2OCH3 H H C2H5Br H C2H5 1 COCH2OCH3 H H n-C3H7Br H C2H5 2 H H H CH3Br H C2H5 2 H H H C2H5Br H C2H5 2 H H H n-C3H7Br H C2H5 2 H H H i-C3H7Br H C2H5 2 H H H i-C4H9Br H C2H5 2 H H H CH2CF3Br H C2H5 2 C2H5 H H CH3Br H C2H5 2 C2H5 H H C2H5Br H C2H5 2 C2H5 H H n-C3H7Br H C2H5 2 C2H5 H H i-C3H7Br H C2H5 2 i-C3H7 H H CH3Br H C2H5 2 i-C3H7 H H C2H5Br H C2H5 2 i-C3H7 H H n-C3H7Br H C2H5 2 i-C3H7 H H iso-C3H7Br H C2H5 2 CH2OCH3 H H C2H5Br H C2H5 2 COC2H5 H H CH3Br H C2H5 2 COC2H5 H H C2H5Br H C2H5 2 COC2H5 H H n-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H C2H5 2 COC3H7-n H H CH3Br H C2H5 2 COC3H7-n H H C2H5Br H C2H5 2 COC3H7-n H H i-C3H7Br H C2H5 2 COC3H7-n H H n-C3H7Br H C2H5 2 COCH2OCH3 H H CH3Br H C2H5 2 COCH2OCH3 H H C2H5Br H C2H5 2 COCH2OCH3 H H n-C3H7Br H n-C3H7 0 H H H C2H5Br H n-C3H7 1 H H H CH3Br H n-C3H7 1 H H H C2H5Br H n-C3H7 1 H H H n-C3H7Br H n-C3H7 1 H H H i-C3H7Br H n-C3H7 1 H H H i-C4H9Br H n-C3H7 1 H H H CH2CF3Br H n-C3H7 2 H H H CH3Br H n-C3H7 2 H H H C2H5Br H n-C3H7 2 H H H n-C3H7Br H n-C3H7 2 H H H i-C3H7Br H n-C3H7 2 H H H i-C4H9Br H n-C3H7 2 H H H CH2CF3Br H CH2CH=CH2 0 H H H C2H5Br H CH2CH=CH2 2 H H H C2H5Br H CH2F 1 H H H CH3Br H CH2F 1 H H H C2H5Br H CH2F 1 H H H n-C3H7Br H CH2F 1 H H H i-C3H7Br H CH2F 1 H H H i-C4H9Br H CH2F 1 H H H CH2CF3Br H CHF2 0 H H H C2H5Br H CHF2 0 H H H CH2CF3Br H CHF2 0 H H H CH3Br H CHF2 0 H H H i-C4H9Br H CHF2 0 H H H n-C3H7Br H CHF2 1 H H H CH3Br H CHF2 1 H H H C2H5Br H CHF2 1 H H H n-C3H7Br H CHF2 1 H H H i-C3H7Br H CHF2 1 H H H i-C4H9Br H CHF2 1 H H H CH2CF3Br H CF3 0 H H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H CF3 0 H H H CH2CF3Br H CF3 0 H H H CH3Br H CF3 0 H H H i-C4H9Br H CF3 0 H H H n-C4H9Br H CH2CH2F 0 H H H CH3Br H CH2CH2F 0 H H H C2H5Br H CH2CH2F 1 H H H CH3Br H CH2CH2F 1 H H H C2H5Br H CH2CH2F 1 H H H n-C3H7Br H CH2CH2F 1 H H H i-C3H7Br H CH2CH2F 1 H H H i-C4H9Br H CH2CH2F 1 H H H CH2CF3Br H CH2CH2F 2 H H H CH3Br H CH2CH2F 2 H H H C2H5Br H CH2CH2F 2 H H H n-C3H7Br H CH2CH2F 2 H H H i-C3H7Br H CH2CH2F 2 H H H i-C4H9Br H CH2CH2F 2 H H H CH2CF3Br H CH2CHF2 0 H H H C2H5Br H CH2CHF2 0 H H H CH3Br H CH2CHF2 1 H H H CH3Br H CH2CHF2 1 H H H C2H5Br H CH2CHF2 1 H H H n-C3H7Br H CH2CHF2 1 H H H i-C3H7Br H CH2CHF2 1 H H H i-C4H9Br H CH2CHF2 1 H H H CH2CF3Br H CH2CHF2 2 H H H C2H5Br H CH2CHF2 2 H H H CH3Br H CH2CF3 0 H H H C2H5Br H CH2CF3 0 H H H CH3Br H CH2CF3 0 C2H5 H H C2H5Br H CH2CF3 0 C2H5 H H CH3Br H CH2CF3 1 H H H CH3Br H CH2CF3 1 H H H C2H5Br H CH2CF3 1 H H H n-C3H7Br H CH2CF3 1 H H H i-C3H7Br H CH2CF3 1 H H H i-C4H9Br H CH2CF3 1 H H H CH2CF3Br H CH2CF3 2 H H H CH3Br H CH2CF3 2 H H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H CH2CF3 2 H H H n-C3H7Br H CH2CF3 2 H H H i-C3H7Br H CH2CF3 2 H H H i-C4H9Br H CH2CF3 2 H H H CH2CF3Br CH3 CH3 0 H H H CH3Br CH3 CH3 0 H H H C2H5Br CH3 CH3 1 H H H CH3Br CH3 CH3 1 H H H C2H5Br CH3 CH3 2 H H H CH3Br CH3 CH3 2 H H H C2H5I H CH3 0 H H H CH3I H CH3 0 H H H C2H5I H CH3 0 H H H i-C4H9I H CH3 1 H H H C2H5I H CH3 1 H H H CH3I H CH3 1 H H H i-C4H9I H CH3 2 H H H CH3I H CH3 2 H H H C2H5I H CH3 2 H H H i-C4H9I H C2H5 0 H H H C2H5I H C2H5 1 H H H CH3I H C2H5 1 H H H C2H5I H C2H5 2 H H H C2H5I H C2H5 2 H H H CH3I H CHF2 0 H H H C2H5I H CF3 0 H H H C2H5I H CH2CH2F 0 H H H C2H5I H CH2CHF2 0 H H H C2H5I H CH2CF3 0 H H H C2H5Cl H CH3 0 CH2CN H H CH3Cl H CH3 0 CH2CN H H C2H5Cl H CH3 0 CH=CH2 H H CH3Cl H CH3 0 CH=CH2 H H C2H5Cl H CH3 0 CH2CH=CH2 H H CH3Cl H CH3 0 CH2CH=CH2 H H C2H5Cl H CH3 0 CH2C≡CH H H CH3Cl H CH3 0 CH2C≡CH H H C2H5Cl H CH3 0 CO2CH3 H H CH3Cl H CH3 0 CO2CH3 H H C2H5Cl H CH3 0 CO2CH3 H H n-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 0 CO2CH3 H H i-C3H7Cl H CH3 0 CO2CH3 H H n-C4H9Cl H CH3 0 CO2CH3 H H i-C4H9Cl H CH3 0 CO2CH3 H H s-C4H9Cl H CH3 0 CO2CH3 H H CH2CF3Cl H CH3 0 CO2CH3 H H
Cl H CH3 0 CO2C2H5 H H C2H5Cl H CH3 0 CO2C2H5 H H n-C3H7Cl H CH3 0 CO2C2H5 H H i-C3H7Cl H CH3 0 CO2C2H5 H H n-C4H9Cl H CH3 0 CO2C2H5 H H i-C4H9Cl H CH3 0 CO2C2H5 H H s-C4H9Cl H CH3 0 CO2C2H5 H H CH2CF3Cl H CH3 0 CO2C2H5 H H
Cl H CH3 1 CO2CH3 H H CH3Cl H CH3 1 CO2CH3 H H C2H5Cl H CH3 1 CO2CH3 H H n-C3H7Cl H CH3 1 CO2CH3 H H i-C3H7Cl H CH3 1 CO2CH3 H H n-C4H9Cl H CH3 1 CO2CH3 H H i-C4H9Cl H CH3 1 CO2CH3 H H s-C4H9Cl H CH3 1 CO2CH3 H H CH2CF3Cl H CH3 1 CO2CH3 H H
Cl H CH3 1 CO2C2H5 H H C2H5Cl H CH3 1 CO2C2H5 H H n-C3H7Cl H CH3 1 CO2C2H5 H H i-C3H7Cl H CH3 1 CO2C2H5 H H n-C4H9Cl H CH3 1 CO2C2H5 H H i-C4H9Cl H CH3 1 CO2C2H5 H H s-C4H9Cl H CH3 1 CO2C2H5 H H CH2CF3Cl H CH3 1 CO2C2H5 H H
Cl H CH3 2 CO2CH3 H H CH3Cl H CH3 2 CO2CH3 H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 2 CO2CH3 H H n-C3H7Cl H CH3 2 CO2CH3 H H i-C3H7Cl H CH3 2 CO2CH3 H H n-C4H9Cl H CH3 2 CO2CH3 H H i-C4H9Cl H CH3 2 CO2CH3 H H s-C4H9Cl H CH3 2 CO2CH3 H H CH2CF3Cl H CH3 2 CO2CH3 H H
Cl H CH3 2 CO2C2H5 H H C2H5Cl H CH3 2 CO2C2H5 H H n-C3H7Cl H CH3 2 CO2C2H5 H H i-C3H7Cl H CH3 2 CO2C2H5 H H n-C4H9Cl H CH3 2 CO2C2H5 H H i-C4H9Cl H CH3 2 CO2C2H5 H H s-C4H9Cl H CH3 2 CO2C2H5 H H CH2CF3Cl H CH3 2 CO2C2H5 H H
Br H CH3 2 CO2CH3 H H CH3Br H CH3 2 CO2CH3 H H C2H5Br H CH3 2 CO2CH3 H H n-C3H7Br H CH3 2 CO2CH3 H H i-C3H7Br H CH3 2 CO2CH3 H H n-C4H9Br H CH3 2 CO2CH3 H H i-C4H9Br H CH3 2 CO2CH3 H H s-C4H9Br H CH3 2 CO2CH3 H H CH2CF3Br H CH3 2 CO2CH3 H H
Br H CH3 2 CO2C2H5 H H C2H5Br H CH3 2 CO2C2H5 H H n-C3H7Br H CH3 2 CO2C2H5 H H i-C3H7Br H CH3 2 CO2C2H5 H H n-C4H9Br H CH3 2 CO2C2H5 H H i-C4H9Br H CH3 2 CO2C2H5 H H s-C4H9Br H CH3 2 CO2C2H5 H H CH2CF3Br H CH3 2 CO2C2H5 H H
Br H CH3 1 CO2CH3 H H CH3Br H CH3 1 CO2CH3 H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H CH3 1 CO2CH3 H H n-C3H7Br H CH3 1 CO2CH3 H H i-C3H7Br H CH3 1 CO2CH3 H H n-C4H9Br H CH3 1 CO2CH3 H H i-C4H9Br H CH3 1 CO2CH3 H H s-C4H9Br H CH3 1 CO2CH3 H H CH2CF3Br H CH3 1 CO2CH3 H H
Br H CH3 1 CO2C2H5 H H C2H5Br H CH3 1 CO2C2H5 H H n-C3H7Br H CH3 1 CO2C2H5 H H i-C3H7Br H CH3 1 CO2C2H5 H H n-C4H9Br H CH3 1 CO2C2H5 H H i-C4H9Br H CH3 1 CO2C2H5 H H s-C4H9Br H CH3 1 CO2C2H5 H H CH2CF3Br H CH3 1 CO2C2H5 H H
Br H CH3 0 CO2CH3 H H CH3Br H CH3 0 CO2CH3 H H C2H5Br H CH3 0 CO2CH3 H H n-C3H7Br H CH3 0 CO2CH3 H H i-C3H7Br H CH3 0 CO2CH3 H H n-C4H9Br H CH3 0 CO2CH3 H H i-C4H9Br H CH3 0 CO2CH3 H H s-C4H9Br H CH3 0 CO2CH3 H H CH2CF3Br H CH3 0 CO2CH3 H H
Br H CH3 0 CO2C2H5 H H C2H5Br H CH3 0 CO2C2H5 H H n-C3H7Br H CH3 0 CO2C2H5 H H i-C3H7Br H CH3 0 CO2C2H5 H H n-C4H9Br H CH3 0 CO2C2H5 H H i-C4H9Br H CH3 0 CO2C2H5 H H s-C4H9Br H CH3 0 CO2C2H5 H H CH2CF3Br H CH3 0 CO2C2H5 H H
Br H C2H5 0 C2H5 H H
Br H C2H5 0 C2H5 H H CH2Si(CH3)3
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H C2H5 0 CH3 H H CH2CF3Br H C2H5 0 CH3 H H
Br H C2H5 0 CH3 H H CH2Si(CH3)3Br H C2H5 0 H H H s-C4H9Br H C2H5 0 H H H
Br H C2H5 0 H H H CH2Si(CH3)3Br H C2H5 0 i-C3H7 H H
Br H C2H5 0 i-C3H7 H H CH2Si(CH3)3Br H C2H5 0 i-C3H7 H H n-C4H9Br H C2H5 0 n-C3H7 H H CH3Br H C2H5 0 n-C3H7 H H C2H5Br H C2H5 0 n-C3H7 H H CH2CF3Br H C2H5 0 n-C3H7 H H
Br H C2H5 0 n-C3H7 H H CH2Si(CH3)3Br H C2H5 0 n-C4H9 H H CH3Br H C2H5 0 n-C4H9 H H C2H5Br H C2H5 1 C2H5 H H CH2CF3Br H C2H5 1 C2H5 H H
Br H C2H5 1 C2H5 H H CH2Si(CH3)3Br H C2H5 1 CH3 H H CH3Br H C2H5 1 CH3 H H C2H5Br H C2H5 1 CH3 H H CH2CF3Br H C2H5 1 CH3 H H
Br H C2H5 1 CH3 H H CH2Si(CH3)3Br H C2H5 1 H H H n-C4H9Br H C2H5 1 H H H s-C4H9Br H C2H5 1 H H H
Br H C2H5 1 H H H CH2Si(CH3)3Br H C2H5 1 i-C3H7 H H i-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H C2H5 1 i-C3H7 H H CH2CF3Br H C2H5 1 i-C3H7 H H
Br H C2H5 1 i-C3H7 H H CH2Si(CH3)3Br H C2H5 1 n-C3H7 H H CH3Br H C2H5 1 n-C3H7 H H C2H5Br H C2H5 1 n-C3H7 H H CH2CF3Br H C2H5 1 n-C3H7 H H
Br H C2H5 1 n-C3H7 H H CH2Si(CH3)3Br H C2H5 1 n-C4H9 H H CH3Br H C2H5 1 n-C4H9 H H C2H5Br H C2H5 2 C2H5 H H CH2CF3Br H C2H5 2 C2H5 H H
Br H C2H5 2 C2H5 H H CH2Si(CH3)3Br H C2H5 2 CH3 H H CH3Br H C2H5 2 CH3 H H C2H5Br H C2H5 2 CH3 H H CH2CF3Br H C2H5 2 CH3 H H
Br H C2H5 2 CH3 H H CH2Si(CH3)3Br H C2H5 2 H H H n-C4H9Br H C2H5 2 H H H s-C4H9Br H C2H5 2 H H H
Br H C2H5 2 H H H CH2Si(CH3)3Br H C2H5 2 i-C3H7 H H CH2CF3Br H C2H5 2 i-C3H7 H H
Br H C2H5 2 i-C3H7 H H CH2Si(CH3)3Br H C2H5 2 n-C3H7 H H CH3Br H C2H5 2 n-C3H7 H H C2H5Br H C2H5 2 n-C3H7 H H CH2CF3Br H C2H5 2 n-C3H7 H H
Br H C2H5 2 n-C3H7 H H CH2Si(CH3)3
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H C2H5 2 n-C4H9 H H CH3Br H C2H5 2 n-C4H9 H H C2H5Br H CH2CF3 0 H H H n-C3H7Br H CH2CF3 0 H H H i-C3H7Br H CH2CF3 0 H H H i-C4H9Br H CH2CF3 0 H H H CH2CF3Br H CH3 0 C2H5 H H
Br H CH3 0 C2H5 H H CH2Si(CH3)3Br H CH3 0 CH3 H H CH2CF3Br H CH3 0 CH3 H H
Br H CH3 0 CH3 H H CH2Si(CH3)3Br H CH3 0 H H H
Br H CH3 0 H H H CH2Si(CH3)3Br H CH3 0 i-C3H7 H H
Br H CH3 0 i-C3H7 H H CH2Si(CH3)3Br H CH3 0 i-C3H7 H H n-C4H9Br H CH3 0 n-C3H7 H H C2H5Br H CH3 0 n-C3H7 H H CH3Br H CH3 0 n-C3H7 H H CH2CF3Br H CH3 0 n-C3H7 H H
Br H CH3 0 n-C3H7 H H CH2Si(CH3)3Br H CH3 0 n-C4H9 H H CH3Br H CH3 0 n-C4H9 H H C2H5Br H CH3 1 C2H5 H H CH2CF3Br H CH3 1 C2H5 H H
Br H CH3 1 C2H5 H H CH2Si(CH3)3Br H CH3 1 CH3 H H C2H5Br H CH3 1 CH3 H H CH3Br H CH3 1 CH3 H H CH2CF3Br H CH3 1 CH3 H H
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H CH3 1 CH3 H H CH2Si(CH3)3Br H CH3 1 H H H n-C4H9Br H CH3 1 H H H s-C4H9Br H CH3 1 H H H
Br H CH3 1 H H H CH2Si(CH3)3Br H CH3 1 i-C3H7 H H CH2CF3Br H CH3 1 i-C3H7 H H
Br H CH3 1 i-C3H7 H H CH2Si(CH3)3Br H CH3 1 n-C3H7 H H C2H5Br H CH3 1 n-C3H7 H H CH3Br H CH3 1 n-C3H7 H H CH2CF3Br H CH3 1 n-C3H7 H H
Br H CH3 1 n-C3H7 H H CH2Si(CH3)3Br H CH3 1 n-C4H9 H H CH3Br H CH3 1 n-C4H9 H H C2H5Br H CH3 2 C2H5 H H CH2CF3Br H CH3 2 C2H5 H H
Br H CH3 2 C2H5 H H CH2Si(CH3)3Br H CH3 2 CH3 H H C2H5Br H CH3 2 CH3 H H CH3Br H CH3 2 CH3 H H CH2CF3Br H CH3 2 CH3 H H
Br H CH3 2 CH3 H H CH2Si(CH3)3Br H CH3 2 H H H n-C4H9Br H CH3 2 H H H s-C4H9Br H CH3 2 H H H
Br H CH3 2 H H H i-C4H9Br H CH3 2 H H H CH2Si(CH3)3Br H CH3 2 i-C3H7 H H CH2CF3Br H CH3 2 i-C3H7 H H
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H CH3 2 i-C3H7 H H CH2Si(CH3)3Br H CH3 2 n-C3H7 H H C2H5Br H CH3 2 n-C3H7 H H CH3Br H CH3 2 n-C3H7 H H CH2CF3Br H CH3 2 n-C3H7 H H
Br H CH3 2 n-C3H7 H H CH2Si(CH3)3Br H CH3 2 n-C4H9 H H CH3Br H CH3 2 n-C4H9 H H C2H5Cl H C2H5 0 C2H5 H H
Cl H C2H5 0 C2H5 H H CH2Si(CH3)3Cl H C2H5 0 C2H5 H H CH2CF2CHF2Cl H C2H5 0 CH=CH2 H H C2H5Cl H C2H5 0 CH2CF3 H H C2H5Cl H C2H5 0 CH2CHF2 H H C2H5Cl H C2H5 0 CH3 H H CH2CF3Cl H C2H5 0 CH3 H H
Cl H C2H5 0 CH3 H H CH2Si(CH3)3Cl H C2H5 0 CH3 H H CH2CF2CHF2Cl H C2H5 0 H H H
Cl H C2H5 0 H H H
Cl H C2H5 0 H H H
Cl H C2H5 0 H H H CH2CF2CHF2Cl H C2H5 0 i-C3H7 H H
Cl H C2H5 0 i-C3H7 H H CH2Si(CH3)3Cl H C2H5 0 n-C3H7 H H CH2CF3Cl H C2H5 0 n-C3H7 H H
Cl H C2H5 0 n-C3H7 H H CH2Si(CH3)3Cl H C2H5 0 n-C3H7 H H CH2CF2CHF2Cl H C2H5 1 C2H5 H H
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H C2H5 1 C2H5 H H CH2Si(CH3)3Cl H C2H5 1 C2H5 H H CH2CF2CHF2Cl H C2H5 1 CH3 H H C2H5Cl H C2H5 1 CH3 H H CH3Cl H C2H5 1 CH3 H H n-C3H7Cl H C2H5 1 CH3 H H i-C3H7Cl H C2H5 1 CH3 H H CH2CF3Cl H C2H5 1 CH3 H H
Cl H C2H5 1 CH3 H H CH2Si(CH3)3Cl H C2H5 1 H H H n-C4H9Cl H C2H5 1 H H H s-C4H9Cl H C2H5 1 H H H
Cl H C2H5 1 H H H CH2Si(CH3)3Cl H C2H5 1 H H H CH2CF2CHF2Cl H C2H5 1 i-C3H7 H H CH2CF3Cl H C2H5 1 i-C3H7 H H
Cl H C2H5 1 i-C3H7 H H CH2Si(CH3)3Cl H C2H5 1 n-C3H7 H H C2H5Cl H C2H5 1 n-C3H7 H H CH3Cl H C2H5 1 n-C3H7 H H n-C3H7Cl H C2H5 1 n-C3H7 H H i-C3H7Cl H C2H5 1 n-C3H7 H H CH2CF3Cl H C2H5 1 n-C3H7 H H
Cl H C2H5 1 n-C3H7 H H CH2Si(CH3)3Cl H C2H5 1 n-C3H7 H H CH2CF2CHF2Cl H C2H5 1 n-C4H9 H H CH3Cl H C2H5 1 n-C4H9 H H C2H5Cl H C2H5 2 C2H5 H H
Cl H C2H5 2 C2H5 H H CH2Si(CH3)3Cl H C2H5 2 C2H5 H H CH2CF2CHF2Cl H C2H5 2 CH3 H H C2H5Cl H C2H5 2 CH3 H H CH3Cl H C2H5 2 CH3 H H n-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H C2H5 2 CH3 H H i-C3H7Cl H C2H5 2 CH3 H H CH2CF3Cl H C2H5 2 CH3 H H
Cl H C2H5 2 CH3 H H CH2Si(CH3)3Cl H C2H5 2 H H H n-C4H9Cl H C2H5 2 H H H i-C4H9Cl H C2H5 2 H H H s-C4H9Cl H C2H5 2 H H H
Cl H C2H5 2 H H H CH2Si(CH3)3Cl H C2H5 2 H H H CH2CF2CHF2Cl H C2H5 2 i-C3H7 H H CH2CF3Cl H C2H5 2 i-C3H7 H H
Cl H C2H5 2 i-C3H7 H H CH2Si(CH3)3Cl H C2H5 2 n-C3H7 H H C2H5Cl H C2H5 2 n-C3H7 H H CH3Cl H C2H5 2 n-C3H7 H H n-C3H7Cl H C2H5 2 n-C3H7 H H i-C3H7Cl H C2H5 2 n-C3H7 H H CH2CF3Cl H C2H5 2 n-C3H7 H H
Cl H C2H5 2 n-C3H7 H H CH2Si(CH3)3Cl H C2H5 2 n-C3H7 H H CH2CF2CHF2Cl H C2H5 2 n-C4H9 H H CH3Cl H C2H5 2 n-C4H9 H H C2H5Cl H CH2CH=CHCH3 0 H H H C2H5Cl H CH2CH2CH2F 1 H H H C2H5Cl H CH2CH2Cl 1 H H H C2H5Cl H CH3 0 C2H5 H H
Cl H CH3 0 C2H5 H H CH2Si(CH3)3Cl H CH3 0 C2H5 H H CH2CF2CHF2Cl H CH3 0 CH2C≡CH H H C2H5Cl H CH3 0 CH2CH=CH2 H H C2H5Cl H CH3 0 CH2CH2Cl H H C2H5Cl H CH3 0 CH2CH2F H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 0 CH2CN H H C2H5Cl H CH3 0 CH3 H H n-C4H9Cl H CH3 0 CH3 H H i-C4H9Cl H CH3 0 CH3 H H s-C4H9Cl H CH3 0 CH3 H H
Cl H CH3 0 CH3 H H CH2Si(CH3)3Cl H CH3 0 CH3 H H CH2CF2CHF2Cl H CH3 0 H H H
Cl H CH3 0 H H H CH2CF2CHF2Cl H CH3 0 i-C3H7 H H
Cl H CH3 0 i-C3H7 H H CH2Si(CH3)3Cl H CH3 0 i-C4H9 H H C2H5Cl H CH3 0 i-C4H9 H H CH3Cl H CH3 0 n-C3H7 H H
Cl H CH3 0 n-C3H7 H H CH2Si(CH3)3Cl H CH3 0 n-C3H7 H H CH2CF2CHF2Cl H CH3 0 n-C6H13 H H C2H5Cl H CH3 0 n-C7H15 H H C2H5Cl H CH3 1 C2H5 H H
Cl H CH3 1 C2H5 H H CH2Si(CH3)3Cl H CH3 1 C2H5 H H CH2CF2CHF2Cl H CH3 1 CH3 H H CH3Cl H CH3 1 CH3 H H n-C3H7Cl H CH3 1 CH3 H H i-C3H7Cl H CH3 1 CH3 H H
Cl H CH3 1 CH3 H H CH2Si(CH3)3Cl H CH3 1 H H H n-C4H9Cl H CH3 1 H H H s-C4H9Cl H CH3 1 H H H
Cl H CH3 1 H H H CH2Si(CH3)3
表1(续)R1R2 R3 n R5 R6 R7 R9Cl H CH3 1 H H H CH2CF2CHF2Cl H CH3 1 i-C3H7 H H CH2CF3Cl H CH3 1 i-C3H7 H H
Cl H CH3 1 i-C3H7 H H CH2Si(CH3)3Cl H CH3 1 n-C3H7 H H C2H5Cl H CH3 1 n-C3H7 H H CH3Cl H CH3 1 n-C3H7 H H CH2CF3Cl H CH3 1 n-C3H7 H H
Cl H CH3 1 n-C3H7 H H CH2Si(CH3)3Cl H CH3 1 n-C3H7 H H CH2CF2CHF2Cl H CH3 1 n-C4H9 H H C2H5Cl H CH3 1 n-C4H9 H H CH3Cl H CH3 2 C2H5 H H
Cl H CH3 2 C2H5 H H CH2Si(CH3)3Cl H CH3 2 C2H5 H H CH2CF2CHF2Cl H CH3 2 CH3 H H CH3Cl H CH3 2 CH3 H H n-C3H7Cl H CH3 2 CH3 H H i-C3H7Cl H CH3 2 CH3 H H CH2CF3Cl H CH3 2 CH3 H H
Cl H CH3 2 CH3 H H CH2Si(CH3)3Cl H CH3 2 H H H n-C4H9Cl H CH3 2 H H H
Cl H CH3 2 H H H CH2Si(CH3)3Cl H CH3 2 H H H CH2CF2CHF2Cl H CH3 2 i-C3H7 H H CH2CF3Cl H CH3 2 i-C3H7 H H
Cl H CH3 2 i-C3H7 H H CH2Si(CH3)3Cl H CH3 2 n-C3H7 H H C2H5Cl H CH3 2 n-C3H7 H H CH3Cl H CH3 2 n-C3H7 H H CH2CF3
表1(续)R1R2 R3 n R5 R6 R7 R9Cl H CH3 2 n-C3H7 H H
Cl H CH3 2 n-C3H7 H H CH2Si(CH3)3Cl H CH3 2 n-C3H7 H H CH2CF2CHF2Cl H CH3 2 n-C4H9 H H C2H5Cl H CH3 2 n-C4H9 H H CH3Cl H CN 0 H H H C2H5Cl H CSOC2H3 0 H H H C2H5Cl H COCH3 0 H H H C2H5Cl H s-C4H9 0 H H H CH3F H n-C3H7 0 H H H C2H5F H n-C3H7 0 H H H CH3Cl H CH3 0 CO2CH3 H H
Cl H CH3 1 CO2CH3 H H
Cl H CH3 2 CO2CH3 H H
Cl H CH3 0 CO2CH3 H H
Cl H CH3 1 CO2CH3 H H
Cl H CH3 2 CO2CH3 H H
Cl H CH3 0 CO2C2H5 H H
Cl H CH3 1 CO2C2H5 H H
Cl H CH3 2 CO2C2H5 H H
Cl H CH3 0 CO2C2H5 H H
Cl H CH3 1 CO2C2H5 H H
Cl H CH3 2 CO2C2H5 H H
Cl H C2H5 0 CO2CH3 H H CH3Cl H C2H5 0 CO2CH3 H H C2H5Cl H C2H5 0 CO2CH3 H H n-C3H7Cl H C2H5 0 CO2CH3 H H i-C3H7Cl H C2H5 0 CO2CH3 H H n-C4H9Cl H C2H5 0 CO2CH3 H H i-C4H9
表1(续)R1R2 R3 n R5 R6 R7 R9Cl H C2H5 0 CO2CH3 H H s-C4H9Cl H C2H5 0 CO2CH3 H H CH2CF3Cl H C2H5 0 CO2CH3 H H
Cl H C2H5 0 CO2C2H5 H H C2H5Cl H C2H5 0 CO2C2H5 H H n-C3H7Cl H C2H5 0 CO2C2H5 H H i-C3H7Cl H C2H5 0 CO2C2H5 H H n-C4H9Cl H C2H5 0 CO2C2H5 H H i-C4H9Cl H C2H5 0 CO2C2H5 H H s-C4H9Cl H C2H5 0 CO2C2H5 H H CH2CF3Cl H C2H5 0 CO2C2H5 H H
Cl H C2H5 1 CO2CH3 H H CH3Cl H C2H5 1 CO2CH3 H H C2H5Cl H C2H5 1 CO2CH3 H H n-C3H7Cl H C2H5 1 CO2CH3 H H i-C3H7Cl H C2H5 1 CO2CH3 H H n-C4H9Cl H C2H5 1 CO2CH3 H H i-C4H9Cl H C2H5 1 CO2CH3 H H s-C4H9Cl H C2H5 1 CO2CH3 H H CH2CF3Cl H C2H5 1 CO2CH3 H H
Cl H C2H5 1 CO2C2H5 H H C2H5Cl H C2H5 1 CO2C2H5 H H n-C3H7Cl H C2H5 1 CO2C2H5 H H i-C3H7Cl H C2H5 1 CO2C2H5 H H n-C4H9Cl H C2H5 1 CO2C2H5 H H i-C4H9Cl H C2H5 1 CO2C2H5 H H s-C4H9Cl H C2H5 1 CO2C2H5 H H CH2CF3Cl H C2H5 1 CO2C2H5 H H
Cl H C2H5 2 CO2CH3 H H CH3Cl H C2H5 2 CO2CH3 H H C2H5Cl H C2H5 2 CO2CH3 H H n-C3H7Cl H C2H5 2 CO2CH3 H H i-C3H7
表1(续)R1R2 R3 n R5 R6 R7 R9Cl H C2H5 2 CO2CH3 H H n-C4H9Cl H C2H5 2 CO2CH3 H H i-C4H9Cl H C2H5 2 CO2CH3 H H s-C4H9Cl H C2H5 2 CO2CH3 H H CH2CF3Cl H C2H5 2 CO2CH3 H H
Cl H C2H5 2 CO2C2H5 H H C2H5Cl H C2H5 2 CO2C2H5 H H n-C3H7Cl H C2H5 2 CO2C2H5 H H i-C3H7Cl H C2H5 2 CO2C2H5 H H n-C4H9Cl H C2H5 2 CO2C2H5 H H i-C4H9Cl H C2H5 2 CO2C2H5 H H s-C4H9Cl H C2H5 2 CO2C2H5 H H CH2CF3Cl H C2H5 2 CO2C2H5 H H
Br H C2H5 2 CO2CH3 H H CH3Br H C2H5 2 CO2CH3 H H C2H5Br H C2H5 2 CO2CH3 H H n-C3H7Br H C2H5 2 CO2CH3 H H i-C3H7Br H C2H5 2 CO2CH3 H H n-C4H9Br H C2H5 2 CO2CH3 H H i-C4H9Br H C2H5 2 CO2CH3 H H s-C4H9Br H C2H5 2 CO2CH3 H H CH2CF3Br H C2H5 2 CO2CH3 H H
Br H C2H5 2 CO2C2H5 H H C2H5Br H C2H5 2 CO2C2H5 H H n-C3H7Br H C2H5 2 CO2C2H5 H H i-C3H7Br H C2H5 2 CO2C2H5 H H n-C4H9Br H C2H5 2 CO2C2H5 H H i-C4H9Br H C2H5 2 CO2C2H5 H H s-C4H9Br H C2H5 2 CO2C2H5 H H CH2CF3Br H C2H5 2 CO2C2H5 H H
Br H C2H5 1 CO2CH3 H H CH3Br H C2H5 1 CO2CH3 H H C2H5
表1(续)R1R2 R3 n R5 R6 R7 R9Br H C2H5 1 CO2CH3 H H n-C3H7Br H C2H5 1 CO2CH3 H H i-C3H7Br H C2H5 1 CO2CH3 H H n-C4H9Br H C2H5 1 CO2CH3 H H i-C4H9Br H C2H5 1 CO2CH3 H H s-C4H9Br H C2H5 1 CO2CH3 H H CH2CF3Br H C2H5 1 CO2CH3 H H
Br H C2H5 1 CO2C2H5 H H C2H5Br H C2H5 1 CO2C2H5 H H n-C3H7Br H C2H5 1 CO2C2H5 H H i-C3H7Br H C2H5 1 CO2C2H5 H H n-C4H9Br H C2H5 1 CO2C2H5 H H i-C4H9Br H C2H5 1 CO2C2H5 H H s-C4H9Br H C2H5 1 CO2C2H5 H H CH2CF3Br H C2H5 1 CO2C2H5 H H
Br H C2H5 0 CO2CH3 H H CH3Br H C2H5 0 CO2CH3 H H C2H5Br H C2H5 0 CO2CH3 H H n-C3H7Br H C2H5 0 CO2CH3 H H i-C3H7Br H C2H5 0 CO2CH3 H H n-C4H9Br H C2H5 0 CO2CH3 H H i-C4H9Br H C2H5 0 CO2CH3 H H s-C4H9Br H C2H5 0 CO2CH3 H H CH2CF3Br H C2H5 0 CO2CH3 H H
Br H C2H5 0 CO2C2H5 H H C2H5Br H C2H5 0 CO2C2H5 H H n-C3H7Br H C2H5 0 CO2C2H5 H H i-C3H7Br H C2H5 0 CO2C2H5 H H n-C4H9Br H C2H5 0 CO2C2H5 H H i-C4H9Br H C2H5 0 CO2C2H5 H H s-C4H9Br H C2H5 0 CO2C2H5 H H CH2CF3Br H C2H5 0 CO2C2H5 H H
Cl H C2H5 0 CO2CH3 H H
Cl H C2H5 1 CO2CH3 H H
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H C2H5 2 CO2CH3 H H
Cl H C2H5 0 CO2CH3 H H
Cl H C2H5 1 CO2CH3 H H
Cl H C2H5 2 CO2CH3 H H
Cl H C2H5 0 CO2C2H5 H H
Cl H C2H5 1 CO2C2H5 H H
Cl H C2H5 2 CO2C2H5 H H
Cl H C2H5 0 CO2C2H5 H H
Cl H C2H5 1 CO2C2H5 H H
Cl H C2H5 2 CO2C2H5 H H
Cl H CH3 1 COCH3 H H CH3Cl H CH3 1 COC4H9-n H H CH3Cl H CH3 2 COC4H9-n H H CH3Br H CH3 0 COC4H9-n H H CH3Br H CH3 1 COC4H9-n H H CH3Br H CH3 2 COC4H9-n H H CH3Br H CH3 0
H H CH3Br H CH3 1
H H CH3Br H CH3 2
H H CH3Cl H CH3 1 COC4H9-n H H C2H5Cl H CH3 2 COC4H9-n H H C2H5Br H CH3 0 COC4H9-n H H C2H5Br H CH3 1 COC4H9-n H H C2H5Br H CH3 2 COC4H9-n H H C2H5Br H CH3 0
H H C2H5Br H CH3 1
H H C2H5Br H CH3 2
H H C2H5
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H CH3 1 COC6H5 H H C2H5Cl H CH3 1 COCH3 H H n-C3H7Cl H CH3 1 COC4H9-n H H n-C3H7Cl H CH3 2 COC4H9-n H H n-C3H7Br H CH3 0 COC4H9-n H H n-C3H7Br H CH3 1 COC4H9-n H H n-C3H7Br H CH3 2 COC4H9-n H H n-C3H7Br H CH3 0
H H n-C3H7Br H CH3 1
H H n-C3H7Br H CH3 2
H H n-C3H7Cl H CH3 0 COCH2OCH3 H H n-C3H7Cl H CH3 0 COCH2OCH3 H H i-C3H7Cl H CH3 1 COCH2OCH3 H H i-C3H7Cl H CH3 2 COCH2OCH3 H H i-C3H7Cl H CH3 1 COCH3 H H i-C3H7Cl H CH3 0 COC3H7-i H H i-C3H7Cl H CH3 1 COC4H9-n H H i-C3H7Cl H CH3 2 COC4H9-n H H i-C3H7Cl H CH3 0
H H i-C3H7Cl H CH3 1 COC2H5 H H CH2CF3Cl H CH3 2 COC2H5 H H CH2CF3Cl H CH3 1 COC3H7-n H H CH2CF3Cl H CH3 2 COC3H7-n H H CH2CF3Cl H CH3 0 COC4H9-n H H CH2CF3Cl H CH3 1 COC4H9-n H H CH2CF3Cl H CH3 2 COC4H9-n H H CH2CF3Cl H CH3 0
H H CH2CF3Cl H CH3 1
H H CH2CF3Cl H CH3 2
H H CH2CF3Cl H CH3 0 COC2H5 H H
Cl H CH3 1 COC2H5 H H
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 2 COC2H5 H H
Cl H CH3 0 COC3H7-n H H
Cl H CH3 1 COC3H7-n H H
Cl H CH3 2 COC3H7-n H H
Cl H CH3 0 COC4H9-n H H
Cl H CH3 1 COC4H9-n H H
Cl H CH3 2 COC4H9-n H H
Cl H CH3 0
H H
Cl H CH3 1
H H
Cl H CH3 2
H H
Cl H C2H5 1 COCH3 H H CH3Cl H C2H5 2 COCH3 H H CH3Cl H C2H5 1 COC4H9-n H H CH3Cl H C2H5 2 COC4H9-n H H CH3Br H C2H5 0 COCH3 H H CH3Br H C2H5 0 COC4H9-n H H CH3Br H C2H5 1 COC4H9-n H H CH3Br H C2H5 2 COC4H9-n H H CH3Cl H C2H5 1 COCH3 H H C2H5Cl H C2H5 2 COCH3 H H C2H5Cl H C2H5 1 COC4H9-n H H C2H5Cl H C2H5 2 COC4H9-n H H C2H5Br H C2H5 1 COCH3 H H C2H5Br H C2H5 2 COCH3 H H C2H5Br H C2H5 0 COC4H9-n H H C2H5Br H C2H5 1 COC4H9-n H H C2H5Br H C2H5 2 COC4H9-n H H C2H5Cl H C2H5 1 COCH3 H H n-C3H7Cl H C2H5 2 COCH3 H H n-C3H7Cl H C2H5 1 COC4H9-n H H n-C3H7Cl H C2H5 2 COC4H9-n H H n-C3H7
表1(续)R1 R2 R3 n R5 R6 R7 R9Br H C2H5 0 COC4H9-n H H n-C3H7Br H C2H5 1 COC4H9-n H H n-C3H7Br H C2H5 2 COC4H9-n H H n-C3H7Cl H C2H5 0 COC3H7-iso H H i-C3H7Cl H C2H5 1 COC4H9-n H H i-C3H7Cl H C2H5 2 COC4H9-n H H i-C3H7Cl H C2H5 0
H H i-C3H7Cl H C2H5 2 COC6H5 H H i-C3H7Br H C2H5 1 COC2H5 H H i-C3H7Br H C2H5 2 COC2H5 H H i-C3H7Cl H C2H5 1 COC2H5 H H CH2CF3Cl H C2H5 2 COC2H5 H H CH2CF3Cl H C2H5 1 COC3H7-n H H CH2CF3Cl H C2H5 2 COC3H7-n H H CH2CF3Cl H C2H5 0 COC4H9-n H H CH2CF3Cl H C2H5 1 COC4H9-n H H CH2CF3Cl H C2H5 2 COC4H9-n H H CH2CF3Cl H C2H5 0 COC2H5 H H
Cl H C2H5 1 COC2H5 H H
Cl H C2H5 2 COC2H5 H H
Cl H C2H5 0 COC3H7-n H H
Cl H C2H5 1 COC3H7-n H H
Cl H C2H5 2 COC3H7-n H H
Cl H C2H5 0 COC4H9-n H H
Cl H C2H5 1 COC4H9-n H H
Cl H C2H5 2 COC4H9-n H H
Cl H CH3 0 CO2CH3 H H CH2CH=CH2Cl H CH3 1 CO2CH3 H H CH2CH=CH2Cl H CH3 2 CO2CH3 H H CH2CH=CH2
表1(续)R1 R2 R3 n R5 R6 R7 R9Cl H CH3 0 CO2C2H5 H H CH2CH=CH2Cl H CH3 1 CO2C2H5 H H CH2CH=CH2Cl H CH3 2 CO2C2H5 H H CH2CH=CH2Cl H C2H5 0 CO2CH3 H H CH2CH=CH2Cl H C2H5 1 CO2CH3 H H CH2CH=CH2Cl H C2H5 2 CO2CH3 H H CH2CH=CH2Cl H C2H5 0 CO2C2H5 H H CH2CH=CH2Cl H C2H5 1 CO2C2H5 H H CH2CH=CH2Cl H C2H5 2 CO2C2H5 H H CH2CH=CH2
表2
R1 R2 R3 n R5 R6 R7 R8F H CH3 0 H H H CH3F H CH3 0 H H H C2H5F H CH3 0 H H H n-C3H7F H CH3 0 H H H i-C3H7F H CH3 0 H H H n-C4H9F H CH3 0 H H H i-C4H9F H CH3 0 H H H t-C4H9F H CH3 0 H H H (CH2)3ClF H CH3 0 H H H CH2CNF H CH3 0 H H H C6H5F H CH3 0 H H H
F H CH3 0 H H H
F H CH3 0 H H H
F H CH3 1 H H H CH3F H CH3 1 H H H C2H5F H CH3 1 H H H n-C3H7F H CH3 1 H H H i-C3H7F H CH3 1 H H H n-C4H9F H CH3 1 H H H i-C4H9F H CH3 1 H H H t-C4H9F H CH3 1 H H H (CH2)3ClF H CH3 1 H H H CH2CNF H CH3 1 H H H C6H5F H CH3 1 H H H
F H CH3 1 H H H
F H CH3 1 H H H
表2(续)R1 R2 R3 n R5 R6 R7 R8F H CH3 2 H H H CH3F H CH3 2 H H H C2H5F H CH3 2 H H H n-C3H7F H CH3 2 H H H i-C3H7F H CH3 2 H H H n-C4H9F H CH3 2 H H H i-C4H9F H CH3 2 H H H t-C4H9F H CH3 2 H H H (CH2)3ClF H CH3 2 H H H CH2CNF H CH3 2 H H H C6H5F H CH3 2 H H H
F H CH3 2 H H H
F H CH3 2 H H H
F H C2H5 0 H H H CH3F H C2H5 0 H H H C2H5F H C2H5 0 H H H n-C3H7F H C2H5 0 H H H i-C3H7F H C2H5 0 H H H n-C4H9F H C2H5 0 H H H i-C4H9F H C2H5 0 H H H t-C4H9F H C2H5 0 H H H (CH2)3ClF H C2H5 0 H H H CH2CNF H C2H5 0 H H H C6H5F H C2H5 0 H H H
F H C2H5 0 H H H
F H C2H5 0 H H H
F H C2H5 1 H H H CH3F H C2H5 1 H H H C2H5F H C2H5 1 H H H n-C3H7F H C2H5 1 H H H i-C3H7F H C2H5 1 H H H n-C4H9F H C2H5 1 H H H i-C4H9F H C2H5 1 H H H t-C4H9F H C2H5 1 H H H (CH2)3ClF H C2H5 1 H H H CH2CN
表2(续)R1 R2 R3 n R5 R6 R7 R8F H C2H5 1 H H H C6H5F H C2H5 1 H H H
F H C2H5 1 H H H
F H C2H5 1 H H H
F H C2H5 2 H H H CH3F H C2H5 2 H H H C2H5F H C2H5 2 H H H n-C3H7F H C2H5 2 H H H i-C3H7F H C2H5 2 H H H n-C4H9F H C2H5 2 H H H i-C4H9F H C2H5 2 H H H t-C4H9F H C2H5 2 H H H (CH2)3ClF H C2H5 2 H H H CH2CNF H C2H5 2 H H H C6H5F H C2H5 2 H H H
F H C2H5 2 H H H
F H C2H5 2 H H H
Cl H CH3 0 H H H HCl H CH3 0 H H H CH3Cl H CH3 0 H H H C2H5Cl H CH3 0 H H H n-C3H7Cl H CH3 0 H H H i-C3H7Cl H CH3 0 H H H n-C4H9Cl H CH3 0 H H H s-C4H9Cl H CH3 0 H H H i-C4H9Cl H CH3 0 H H H t-C4H9Cl H CH3 0 H H H n-C5H11Cl H CH3 0 H H H n-C6H13Cl H CH3 0 H H H C6H5Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H CH=CH2Cl H CH3 0 H H H CH=CHC6H5Cl H CH3 0 H H H CH=CHCH3Cl H CH3 0 H H H C(=CH2)CH3Cl H CH3 0 H H H CH2CF=CF2Cl H CH3 0 H H H
Cl H CH3 0 H H H CH2CH2ClCl H CH3 0 H H H (CH2)4ClCl H CH3 0 H H H (CH2)3ClCl H CH3 0 H H H CH2OCH3Cl H CH3 0 H H H CH2CH2OCH3Cl H CH3 0 H H H CH2CNCl H CH3 0 H H H CH2CO2C2H5Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H H H
Cl H CH3 0 H 2-Cl H CH3Cl H CH3 0 H 2-Cl H C2H5Cl H CH3 0 H 2-Cl H n-C3H7Cl H CH3 0 H 2-Cl H n-C4H9Cl H CH3 0 H 3-Cl H CH3
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 0 H 3-Cl H C2H5Cl H CH3 0 H 3-Cl H n-C3H7Cl H CH3 0 H 3-Cl H n-C4H9Cl H CH3 0 H 2-F H CH3Cl H CH3 0 H 2-F H C2H5Cl H CH3 0 H 2-F H n-C3H7Cl H CH3 0 H 2-F H n-C4H9Cl H CH3 0 H 3-F H CH3Cl H CH3 0 H 3-F H C2H5Cl H CH3 0 H 3-F H n-C3H7Cl H CH3 0 H 3-F H n-C4H9Cl H CH3 0 H 3-F H s-C4H9Cl H CH3 0 CH3 H H CH3Cl H CH3 0 CH3 H H C2H5Cl H CH3 0 CH3 H H n-C3H7Cl H CH3 0 CH3 H H i-C3H7Cl H CH3 0 CH3 H H n-C4H9Cl H CH3 0 CH3 H H s-C4H9Cl H CH3 0 CH3 H H t-C4H9Cl H CH3 0 CH3 H H i-C4H9Cl H CH3 0 CH3 H H C6H5Cl H CH3 0 CH3 H H
Cl H CH3 0 CH3 H H (CH2)3ClCl H CH3 0 CH3 H H (CH2)4ClCl H CH3 0 CH3 H H CH2CNCl H CH3 0 CH3 H H CH2OCH3Cl H CH3 0 CH3 H H CH2CO2C2H5Cl H CH3 0 C2H5 H H
Cl H CH3 0 C2H5 H H CH3Cl H CH3 0 C2H5 H H C2H5Cl H CH3 0 C2H5 H H n-C3H7Cl H CH3 0 C2H5 H H i-C3H7Cl H CH3 0 C2H5 H H n-C4H9Cl H CH3 0 C2H5 H H i-C4H9Cl H CH3 0 C2H5 H H s-C4H9Cl H CH3 0 C2H5 H H t-C4H9Cl H CH3 0 C2H5 H H (CH2)3ClCl H CH3 0 C2H5 H H (CH2)4ClCl H CH3 0 C2H5 H H CH2CNCl H CH3 0 C2H5 H H CH2OCH3Cl H CH3 0 C2H5 H H CH2CO2C2H5
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 0 C2H5 H H C6H5Cl H CH3 0 n-C3H7 H H
Cl H CH3 0 n-C3H7 H H CH3Cl H CH3 0 n-C3H7 H H C2H5Cl H CH3 0 n-C3H7 H H n-C3H7Cl H CH3 0 n-C3H7 H H i-C3H7Cl H CH3 0 n-C3H7 H H n-C4H9Cl H CH3 0 n-C3H7 H H i-C4H9Cl H CH3 0 n-C3H7 H H s-C4H9Cl H CH3 0 n-C3H7 H H t-C4H9Cl H CH3 0 n-C3H7 H H (CH2)3ClCl H CH3 0 n-C3H7 H H (CH2)4ClCl H CH3 0 n-C3H7 H H CH2CNCl H CH3 0 n-C3H7 H H CH2CO2C2H5Cl H CH3 0 n-C3H7 H H CH2OCH3Cl H CH3 0 n-C3H7 H H C6H5Cl H CH3 0 i-C3H7 H H CH3Cl H CH3 0 i-C3H7 H H C2H5Cl H CH3 0 i-C3H7 H H n-C3H7Cl H CH3 0 i-C3H7 H H i-C3H7Cl H CH3 0 i-C3H7 H H n-C4H9Cl H CH3 0 i-C3H7 H H i-C4H9Cl H CH3 0 i-C3H7 H H s-C4H9Cl H CH3 0 i-C3H7 H H t-C4H9Cl H CH3 0 i-C3H7 H H (CH2)3ClCl H CH3 0 i-C3H7 H H (CH2)4ClCl H CH3 0 i-C3H7 H H CH2CNCl H CH3 0 i-C3H7 H H CH2CO2C2H5Cl H CH3 0 i-C3H7 H H CH2OCH3Cl H CH3 0 i-C3H7 H H C6H5Cl H CH3 0 i-C3H7 H H
Cl H CH3 0 CH2OCH3 H H CH3Cl H CH3 0 CH2OCH3 H H C6H5Cl H CH3 0 CH2OC2H5 H H CH3Cl H CH3 0 CH2OC2H5 H H C6H5Cl H CH3 0 CH2SCH3 H H CH3Cl H CH3 0 CH2SCH3 H H C6H5Cl H CH3 0 COCH3 H H CH3Cl H CH3 0 COC2H5 H H CH3Cl H CH3 0 COC2H5 H H C2H5Cl H CH3 1 H H H CH3
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 1 H H H C2H5Cl H CH3 1 H H H n-C3H7Cl H CH3 1 H H H i-C3H7Cl H CH3 1 H H H n-C4H9Cl H CH3 1 H H H i-C4H9Cl H CH3 1 H H H t-C4H9Cl H CH3 1 H H H (CH2)3ClCl H CH3 1 H H H CH2CNCl H CH3 1 H H H CH2OCH3Cl H CH3 1 H H H CH2CO2C2H5Cl H CH3 1 H H H
Cl H CH3 1 H H H
Cl H CH3 1 H H H C6H5Cl H CH3 1 H H H
Cl H CH3 1 H 2-Cl H C2H5Cl H CH3 1 H 3-Cl H CH3Cl H CH3 1 CH3 H H CH3Cl H CH3 1 CH3 H H C2H5Cl H CH3 1 CH3 H H n-C3H7Cl H CH3 1 CH3 H H i-C3H7Cl H CH3 1 CH3 H H n-C4H9Cl H CH3 1 CH3 H H i-C4H9Cl H CH3 1 CH3 H H s-C4H9Cl H CH3 1 CH3 H H t-C4H9Cl H CH3 1 CH3 H H (CH2)3ClCl H CH3 1 CH3 H H (CH2)4ClCl H CH3 1 CH3 H H CH2CNCl H CH3 1 CH3 H H CH2CO2C2H5Cl H CH3 1 CH3 H H CH2OCH3Cl H CH3 1 CH3 H H C6H5Cl H CH3 1 CH3 H H
Cl H CH3 1 C2H5 H H CH3Cl H CH3 1 C2H5 H H C2H5Cl H CH3 1 C2H5 H H n-C3H7Cl H CH3 1 C2H5 H H i-C3H7Cl H CH3 1 C2H5 H H n-C4H9Cl H CH3 1 C2H5 H H i-C4H9Cl H CH3 1 C2H5 H H s-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 1 C2H5 H H t-C4H9Cl H CH3 1 C2H5 H H (CH2)3ClCl H CH3 1 C2H5 H H (CH2)4ClCl H CH3 1 C2H5 H H CH2CNCl H CH3 1 C2H5 H H CH2CO2C2H5Cl H CH3 1 C2H5 H H CH2OCH3Cl H CH3 1 C2H5 H H C6H5Cl H CH3 1 C2H5 H H
Cl H CH3 1 n-C3H7 H H CH3Cl H CH3 1 n-C3H7 H H C2H5Cl H CH3 1 n-C3H7 H H n-C3H7Cl H CH3 1 n-C3H7 H H i-C3H7Cl H CH3 1 n-C3H7 H H n-C4H9Cl H CH3 1 n-C3H7 H H i-C4H9Cl H CH3 1 n-C3H7 H H s-C4H9Cl H CH3 1 n-C3H7 H H t-C4H9Cl H CH3 1 n-C3H7 H H (CH2)3ClCl H CH3 1 n-C3H7 H H (CH2)4ClCl H CH3 1 n-C3H7 H H CH2CNCl H CH3 1 n-C3H7 H H CH2CO2C2H5Cl H CH3 1 n-C3H7 H H CH2OCH3Cl H CH3 1 n-C3H7 H H C6H5Cl H CH3 1 n-C3H7 H H
Cl H CH3 1 i-C3H7 H H CH3Cl H CH3 1 i-C3H7 H H C2H5Cl H CH3 1 i-C3H7 H H n-C3H7Cl H CH3 1 i-C3H7 H H i-C3H7Cl H CH3 1 i-C3H7 H H n-C4H9Cl H CH3 1 i-C3H7 H H i-C4H9Cl H CH3 1 i-C3H7 H H s-C4H9Cl H CH3 1 i-C3H7 H H t-C4H9Cl H CH3 1 i-C3H7 H H (CH2)3ClCl H CH3 1 i-C3H7 H H (CH2)4ClCl H CH3 1 i-C3H7 H H CH2CNCl H CH3 1 i-C3H7 H H CH2CO2C2H5Cl H CH3 1 i-C3H7 H H CH2OCH3Cl H CH3 1 i-C3H7 H H C6H5Cl H CH3 1 i-C3H7 H H
Cl H CH3 2 H H H CH3Cl H CH3 2 H H H C2H5
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 2 H H H n-C3H7Cl H CH3 2 H H H i-C3H7Cl H CH3 2 H H H n-C4H9Cl H CH3 2 H H H i-C4H9Cl H CH3 2 H H H t-C4H9Cl H CH3 2 H H H (CH2)3ClCl H CH3 2 H H H CH2CNCl H CH3 2 H H H CH2OCH3Cl H CH3 2 H H H CH2CO2C2H5Cl H CH3 2 H H H
Cl H CH3 2 H H H
Cl H CH3 2 H H H C6H5Cl H CH3 2 H H H
Cl H CH3 2 H 2-Cl H C2H5Cl H CH3 2 H 3-Cl H C2H5Cl H CH3 2 CH3 H H CH3Cl H CH3 2 CH3 H H C2H5Cl H CH3 2 CH3 H H n-C3H7Cl H CH3 2 CH3 H H i-C3H7Cl H CH3 2 CH3 H H n-C4H9Cl H CH3 2 CH3 H H i-C4H9Cl H CH3 2 CH3 H H s-C4H9Cl H CH3 2 CH3 H H t-C4H9Cl H CH3 2 CH3 H H (CH2)3ClCl H CH3 2 CH3 H H (CH2)4ClCl H CH3 2 CH3 H H CH2CNCl H CH3 2 CH3 H H CH2CO2C2H5Cl H CH3 2 CH3 H H CH2OCH3Cl H CH3 2 CH3 H H C6H5Cl H CH3 2 CH3 H H
Cl H CH3 2 C2H5 H H CH3Cl H CH3 2 C2H5 H H C2H5Cl H CH3 2 C2H5 H H n-C3H7Cl H CH3 2 C2H5 H H i-C3H7Cl H CH3 2 C2H5 H H n-C4H9Cl H CH3 2 C2H5 H H i-C4H9Cl H CH3 2 C2H5 H H s-C4H9Cl H CH3 2 C2H5 H H t-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 2 C2H5 H H (CH2)3ClCl H CH3 2 C2H5 H H (CH2)4ClCl H CH3 2 C2H5 H H CH2CNCl H CH3 2 C2H5 H H CH2CO2C2H5Cl H CH3 2 C2H5 H H CH2OCH3Cl H CH3 2 C2H5 H H C6H5Cl H CH3 2 C2H5 H H
Cl H CH3 2 n-C3H7 H H CH3Cl H CH3 2 n-C3H7 H H C2H5Cl H CH3 2 n-C3H7 H H n-C3H7Cl H CH3 2 n-C3H7 H H i-C3H7Cl H CH3 2 n-C3H7 H H n-C4H9Cl H CH3 2 n-C3H7 H H i-C4H9Cl H CH3 2 n-C3H7 H H s-C4H9Cl H CH3 2 n-C3H7 H H t-C4H9Cl H CH3 2 n-C3H7 H H (CH2)3ClCl H CH3 2 n-C3H7 H H (CH2)4ClCl H CH3 2 n-C3H7 H H CH2CNCl H CH3 2 n-C3H7 H H CH2CO2C2H5Cl H CH3 2 n-C3H7 H H CH2OCH3Cl H CH3 2 n-C3H7 H H C6H5Cl H CH3 2 n-C3H7 H H
Cl H CH3 2 i-C3H7 H H CH3Cl H CH3 2 i-C3H7 H H C2H5Cl H CH3 2 i-C3H7 H H n-C3H7Cl H CH3 2 i-C3H7 H H i-C3H7Cl H CH3 2 i-C3H7 H H n-C4H9Cl H CH3 2 i-C3H7 H H i-C4H9Cl H CH3 2 i-C3H7 H H s-C4H9Cl H CH3 2 i-C3H7 H H t-C4H9Cl H CH3 2 i-C3H7 H H C6H5Cl H CH3 2 i-C3H7 H H
Cl H CH3 2 i-C3H7 H H (CH2)3ClCl H CH3 2 i-C3H7 H H (CH2)4ClCl H CH3 2 i-C3H7 H H CH2CNCl H CH3 2 i-C3H7 H H CH2CO2C2H5Cl H CH3 2 i-C3H7 H H CH2OCH3Cl H C2H5 0 H H H CH3Cl H C2H5 0 H H H C2H5Cl H C2H5 0 H H H n-C3H7
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 0 H H H i-C3H7Cl H C2H5 0 H H H n-C4H9Cl H C2H5 0 H H H i-C4H9Cl H C2H5 0 H H H s-C4H9Cl H C2H5 0 H H H t-C4H9Cl H C2H5 0 H H H n-C5H11Cl H C2H5 0 H H H n-C6H13Cl H C2H5 0 H H H C6H5Cl H C2H5 0 H H H
Cl H C2H5 0 H H H
Cl H C2H5 0 H H H
Cl H C2H5 0 H H H
Cl H C2H5 0 H H H
Cl H C2H5 0 H H H
Cl H C2H5 0 H H H CH=CH2Cl H C2H5 0 H H H CH=CHC6H5Cl H C2H5 0 H H H CH2CF=CF2Cl H C2H5 0 H H H (CH2)4ClCl H C2H5 0 H H H (CH2)3ClCl H C2H5 0 H H H CH2CNCl H C2H5 0 H H H CH2OCH3Cl H C2H5 0 H H H CH2CO2C2H5Cl H C2H5 0 CH3 H H CH3Cl H C2H5 0 CH3 H H CH3Cl H C2H5 0 CH3 H H C2H5Cl H C2H5 0 CH3 H H n-C3H7Cl H C2H5 0 CH3 H H i-C3H7Cl H C2H5 0 CH3 H H n-C4H9Cl H C2H5 0 CH3 H H i-C4H9Cl H C2H5 0 CH3 H H s-C4H9Cl H C2H5 0 CH3 H H t-C4H9Cl H C2H5 0 CH3 H H (CH2)3ClCl H C2H5 0 CH3 H H (CH2)4ClCl H C2H5 0 CH3 H H CH2CNCl H C2H5 0 CH3 H H CH2OCH3
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 0 CH3 H H CH2CO2C2H5Cl H C2H5 0 CH3 H H C6H5Cl H C2H5 0 CH3 H H
Cl H C2H5 0 C2H5 H H CH3Cl H C2H5 0 C2H5 H H C2H5Cl H C2H5 0 C2H5 H H n-C3H7Cl H C2H5 0 C2H5 H H i-C3H7Cl H C2H5 0 C2H5 H H n-C4H9Cl H C2H5 0 C2H5 H H i-C4H9Cl H C2H5 0 C2H5 H H s-C4H9Cl H C2H5 0 C2H5 H H t-C4H9Cl H C2H5 0 C2H5 H H (CH2)3ClCl H C2H5 0 C2H5 H H (CH2)4ClCl H C2H5 0 C2H5 H H CH2CNCl H C2H5 0 C2H5 H H CH2OCH3Cl H C2H5 0 C2H5 H H CH2CO2C2H5Cl H C2H5 0 C2H5 H H C6H5Cl H C2H5 0 C2H5 H H
Cl H C2H5 0 n-C3H7 H H CH3Cl H C2H5 0 n-C3H7 H H C2H5Cl H C2H5 0 n-C3H7 H H n-C3H7Cl H C2H5 0 n-C3H7 H H i-C3H7Cl H C2H5 0 n-C3H7 H H n-C4H9Cl H C2H5 0 n-C3H7 H H i-C4H9Cl H C2H5 0 n-C3H7 H H s-C4H9Cl H C2H5 0 n-C3H7 H H t-C4H9Cl H C2H5 0 n-C3H7 H H (CH2)3ClCl H C2H5 0 n-C3H7 H H (CH2)4ClCl H C2H5 0 n-C3H7 H H CH2CNCl H C2H5 0 n-C3H7 H H CH2CO2C2H5Cl H C2H5 0 n-C3H7 H H CH2OCH3Cl H C2H5 0 n-C3H7 H H C6H5Cl H C2H5 0 n-C3H7 H H
Cl H C2H5 0 i-C3H7 H H CH3Cl H C2H5 0 i-C3H7 H H C2H5Cl H C2H5 0 i-C3H7 H H n-C3H7Cl H C2H5 0 i-C3H7 H H i-C3H7Cl H C2H5 0 i-C3H7 H H n-C4H9Cl H C2H5 0 i-C3H7 H H i-C4H9Cl H C2H5 0 i-C3H7 H H s-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 0 CH3 H H CH2CNCl H C2H5 0 CH3 H H CH2OCH3Cl H C2H5 0 i-C3H7 H H t-C4H9Cl H C2H5 0 i-C3H7 H H (CH2)3ClCl H C2H5 0 i-C3H7 H H (CH2)4ClCl H C2H5 0 i-C3H7 H H CH2CNCl H C2H5 0 i-C3H7 H H CH2OCH3Cl H C2H5 0 i-C3H7 H H CH2CO2C2H5Cl H C2H5 0 i-C3H7 H H C6H5Cl H C2H5 0 i-C3H7 H H
Cl H C2H5 0 CH2OCH3 H H CH3Cl H C2H5 0 CH2SCH3 H H CH3Cl H C2H5 0 COC2H5 H H CH3Cl H C2H5 0 COC2H5 H H C2H5Cl H C2H5 0 COC3H7-n H H CH3Cl H C2H5 1 H H H CH3Cl H C2H5 1 H H H C2H5Cl H C2H5 1 H H H n-C3H7Cl H C2H5 1 H H H i-C3H7Cl H C2H5 1 H H H n-C4H9Cl H C2H5 1 H H H i-C4H9Cl H C2H5 1 H H H t-C4H9Cl H C2H5 1 H H H (CH2)3ClCl H C2H5 1 H H H CH2CNCl H C2H5 1 H H H CH2OCH3Cl H C2H5 1 H H H CH2CO2C2H5Cl H C2H5 1 H H H
Cl H C2H5 1 H H H
Cl H C2H5 1 H H H C6H5Cl H C2H5 1 H H H
Cl H C2H5 1 CH3 H H CH3Cl H C2H5 1 CH3 H H C2H5Cl H C2H5 1 CH3 H H n-C3H7Cl H C2H5 1 CH3 H H i-C3H7Cl H C2H5 1 CH3 H H n-C4H9Cl H C2H5 1 CH3 H H i-C4H9Cl H C2H5 1 CH3 H H s-C4H9Cl H C2H5 1 CH3 H H t-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 1 CH3 H H (CH2)3ClCl H C2H5 1 CH3 H H (CH2)4ClCl H C2H5 1 CH3 H H CH2CNCl H C2H5 1 CH3 H H CH2CO2C2H5Cl H C2H5 1 CH3 H H CH2OCH3Cl H C2H5 1 CH3 H H C6H5Cl H C2H5 1 CH3 H H
Cl H C2H5 1 C2H5 H H CH3Cl H C2H5 1 C2H5 H H C2H5Cl H C2H5 1 C2H5 H H n-C3H7Cl H C2H5 1 C2H5 H H i-C3H7Cl H C2H5 1 C2H5 H H n-C4H9Cl H C2H5 1 C2H5 H H i-C4H9Cl H C2H5 1 C2H5 H H s-C4H9Cl H C2H5 1 C2H5 H H t-C4H9Cl H C2H5 1 C2H5 H H (CH2)3ClCl H C2H5 1 C2H5 H H (CH2)4ClCl H C2H5 1 C2H5 H H CH2CNCl H C2H5 1 C2H5 H H CH2OCH3Cl H C2H5 1 C2H5 H H CH2CO2C2H5Cl H C2H5 1 C2H5 H H C6H5Cl H C2H5 1 C2H5 H H
Cl H C2H5 1 n-C3H7 H H CH3Cl H C2H5 1 n-C3H7 H H C2H5Cl H C2H5 1 n-C3H7 H H n-C3H7Cl H C2H5 1 n-C3H7 H H i-C3H7Cl H C2H5 1 n-C3H7 H H n-C4H9Cl H C2H5 1 n-C3H7 H H i-C4H9Cl H C2H5 1 n-C3H7 H H s-C4H9Cl H C2H5 1 n-C3H7 H H t-C4H9Cl H C2H5 1 n-C3H7 H H (CH2)3ClCl H C2H5 1 n-C3H7 H H (CH2)4ClCl H C2H5 1 n-C3H7 H H CH2CNCl H C2H5 1 n-C3H7 H H CH2CO2C2H5Cl H C2H5 1 n-C3H7 H H CH2OCH3Cl H C2H5 1 n-C3H7 H H C6H5Cl H C2H5 1 n-C3H7 H H
Cl H C2H5 1 i-C3H7 H H CH3Cl H C2H5 1 i-C3H7 H H C2H5Cl H C2H5 1 i-C3H7 H H n-C3H7
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 1 i-C3H7 H H i-C3H7Cl H C2H5 1 i-C3H7 H H n-C4H9Cl H C2H5 1 i-C3H7 H H i-C4H9Cl H C2H5 1 i-C3H7 H H s-C4H9Cl H C2H5 1 i-C3H7 H H t-C4H9Cl H C2H5 1 i-C3H7 H H (CH2)3ClCl H C2H5 1 i-C3H7 H H (CH2)4ClCl H C2H5 1 i-C3H7 H H CH2CNCl H C2H5 1 i-C3H7 H H CH2OCH3Cl H C2H5 1 i-C3H7 H H CH2CO2C2H5Cl H C2H5 1 i-C3H7 H H C6H5Cl H C2H5 1 i-C3H7 H H
Cl H C2H5 2 H H H CH3Cl H C2H5 2 H H H C2H5Cl H C2H5 2 H H H n-C3H7Cl H C2H5 2 H H H i-C3H7Cl H C2H5 2 H H H n-C4H9Cl H C2H5 2 H H H i-C4H9Cl H C2H5 2 H H H t-C4H9Cl H C2H5 2 H H H (CH2)3ClCl H C2H5 2 H H H CH2CNCl H C2H5 2 H H H CH2OCH3Cl H C2H5 2 H H H CH2CO2C2H5Cl H C2H5 2 H H H
Cl H C2H5 2 H H H
Cl H C2H5 2 H H H C6H5Cl H C2H5 2 H H H
Cl H C2H5 2 CH3 H H CH3Cl H C2H5 2 CH3 H H C2H5Cl H C2H5 2 CH3 H H n-C3H7Cl H C2H5 2 CH3 H H i-C3H7Cl H C2H5 2 CH3 H H n-C4H9Cl H C2H5 2 CH3 H H i-C4H9Cl H C2H5 2 CH3 H H s-C4H9Cl H C2H5 2 CH3 H H t-C4H9Cl H C2H5 2 CH3 H H (CH2)3ClCl H C2H5 2 CH3 H H (CH2)4ClCl H C2H5 2 CH3 H H CH2CN
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 2 CH3 H H CH2CO2C2H5Cl H C2H5 2 CH3 H H CH2OCH3Cl H C2H5 2 CH3 H H C6H5Cl H C2H5 2 CH3 H H
Cl H C2H5 2 C2H5 H H CH3Cl H C2H5 2 C2H5 H H C2H5Cl H C2H5 2 C2H5 H H n-C3H7Cl H C2H5 2 C2H5 H H i-C3H7Cl H C2H5 2 C2H5 H H n-C4H9Cl H C2H5 2 C2H5 H H i-C4H9Cl H C2H5 2 C2H5 H H s-C4H9Cl H C2H5 2 C2H5 H H t-C4H9Cl H C2H5 2 C2H5 H H (CH2)3ClCl H C2H5 2 C2H5 H H (CH2)4ClCl H C2H5 2 C2H5 H H CH2CNCl H C2H5 2 C2H5 H H CH2CO2C2H5Cl H C2H5 2 C2H5 H H CH2OCH3Cl H C2H5 2 C2H5 H H C6H5Cl H C2H5 2 C2H5 H H
Cl H C2H5 2 n-C3H7 H H CH3Cl H C2H5 2 n-C3H7 H H C2H5Cl H C2H5 2 n-C3H7 H H n-C3H7Cl H C2H5 2 n-C3H7 H H i-C3H7Cl H C2H5 2 n-C3H7 H H n-C4H9Cl H C2H5 2 n-C3H7 H H i-C4H9Cl H C2H5 2 n-C3H7 H H s-C4H9Cl H C2H5 2 n-C3H7 H H t-C4H9Cl H C2H5 2 n-C3H7 H H (CH2)3ClCl H C2H5 2 n-C3H7 H H (CH2)4ClCl H C2H5 2 n-C3H7 H H CH2CNCl H C2H5 2 n-C3H7 H H CH2CO2C2H5Cl H C2H5 2 n-C3H7 H H CH2OCH3Cl H C2H5 2 n-C3H7 H H C6H5Cl H C2H5 2 n-C3H7 H H
Cl H C2H5 2 i-C3H7 H H CH3Cl H C2H5 2 i-C3H7 H H C2H5Cl H C2H5 2 i-C3H7 H H n-C3H7Cl H C2H5 2 i-C3H7 H H i-C3H7Cl H C2H5 2 i-C3H7 H H n-C4H9Cl H C2H5 2 i-C3H7 H H i-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 2 i-C3H7 H H s-C4H9Cl H C2H5 2 i-C3H7 H H t-C4H9Cl H C2H5 2 i-C3H7 H H (CH2)3ClCl H C2H5 2 i-C3H7 H H (CH2)4ClCl H C2H5 2 i-C3H7 H H CH2CNCl H C2H5 2 i-C3H7 H H CH2CO2C2H5Cl H C2H5 2 i-C3H7 H H CH2OCH3Cl H C2H5 2 i-C3H7 H H C6H5Cl H C2H5 2 i-C3H7 H H
Cl H n-C3H7 0 H H H CH3Cl H n-C3H7 0 H H H C2H5Cl H n-C3H7 0 H H H n-C3H7Cl H n-C3H7 0 H H H i-C3H7Cl H n-C3H7 0 H H H n-C4H9Cl H n-C3H7 0 H H H i-C4H9Cl H n-C3H7 0 H H H t-C4H9Cl H n-C3H7 0 H H H (CH2)3ClCl H n-C3H7 0 H H H CH2CNCl H n-C3H7 0 H H H CH2OCH3Cl H n-C3H7 0 H H H CH2CO2C2H5Cl H n-C3H7 0 H H H
Cl H n-C3H7 0 H H H
Cl H n-C3H7 0 H H H C6H5Cl H n-C3H7 0 H H H
Cl H n-C3H7 1 H H H CH3Cl H n-C3H7 1 H H H C2H5Cl H n-C3H7 1 H H H n-C3H7Cl H n-C3H7 1 H H H i-C3H7Cl H n-C3H7 1 H H H n-C4H9Cl H n-C3H7 1 H H H i-C4H9Cl H n-C3H7 1 H H H t-C4H9Cl H n-C3H7 1 H H H (CH2)3ClCl H n-C3H7 1 H H H CH2CNCl H n-C3H7 1 H H H CH2OCH3Cl H n-C3H7 1 H H H CH2CO2C2H5Cl H n-C3H7 1 H H H
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H n-C3H7 1 H H H
Cl H n-C3H7 1 H H H C6H5Cl H n-C3H7 1 H H H
Cl H n-C3H7 2 H H H CH3Cl H n-C3H7 2 H H H C2H5Cl H n-C3H7 2 H H H n-C3H7Cl H n-C3H7 2 H H H i-C3H7Cl H n-C3H7 2 H H H n-C4H9Cl H n-C3H7 2 H H H i-C4H9Cl H n-C3H7 2 H H H t-C4H9Cl H n-C3H7 2 H H H (CH2)3ClCl H n-C3H7 2 H H H CH2CNCl H n-C3H7 2 H H H CH2OCH3Cl H n-C3H7 2 H H H CH2CO2C2H5Cl H n-C3H7 2 H H H
Cl H n-C3H7 2 H H H
Cl H n-C3H7 2 H H H C6H5Cl H n-C3H7 2 H H H
Cl H CH2F 0 H H H CH3Cl H CH2F 0 H H H C2H5Cl H CH2F 0 H H H n-C3H7Cl H CH2F 0 H H H i-C3H7Cl H CH2F 0 H H H n-C4H9Cl H CH2F 0 H H H i-C4H9Cl H CH2F 0 H H H t-C4H9Cl H CH2F 0 H H H (CH2)3ClCl H CH2F 0 H H H CH2CNCl H CH2F 0 H H H CH2OCH3Cl H CH2F 0 H H H CH2CO2C2H5Cl H CH2F 0 H H H
Cl H CH2F 0 H H H
Cl H CH2F 0 H H H C6H5Cl H CH2F 0 H H H
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH2F 1 H H H CH3Cl H CH2F 1 H H H C2H5Cl H CH2F 1 H H H n-C3H7Cl H CH2F 1 H H H i-C3H7Cl H CH2F 1 H H H n-C4H9Cl H CH2F 1 H H H i-C4H9Cl H CH2F 1 H H H t-C4H9Cl H CH2F 1 H H H (CH2)3ClCl H CH2F 1 H H H CH2CNCl H CH2F 1 H H H CH2OCH3Cl H CH2F 1 H H H CH2CO2C2H5Cl H CH2F 1 H H H
Cl H CH2F 1 H H H
Cl H CH2F 1 H H H C6H5Cl H CH2F 1 H H H
Cl H CH2F 2 H H H CH3Cl H CH2F 2 H H H C2H5Cl H CH2F 2 H H H n-C3H7Cl H CH2F 2 H H H i-C3H7Cl H CH2F 2 H H H n-C4H9Cl H CH2F 2 H H H i-C4H9Cl H CH2F 2 H H H t-C4H9Cl H CH2F 2 H H H (CH2)3ClCl H CH2F 2 H H H CH2CNCl H CH2F 2 H H H CH2OCH3Cl H CH2F 2 H H H CH2CO2C2H5Cl H CH2F 2 H H H
Cl H CH2F 2 H H H
Cl H CH2F 2 H H H C6H5Cl H CH2F 2 H H H
Cl H CHF2 0 H H H CH3Cl H CHF2 0 H H H C2H5Cl H CHF2 0 H H H n-C3H7Cl H CHF2 0 H H H i-C3H7Cl H CHF2 0 H H H n-C4H9Cl H CHF2 0 H H H i-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CHF2 0 H H H t-C4H9Cl H CHF2 0 H H H (CH2)3ClCl H CHF2 0 H H H CH2CNCl H CHF2 0 H H H CH2OCH3Cl H CHF2 0 H H H CH2CO2C2H5Cl H CHF2 0 H H H
Cl H CHF2 0 H H H
Cl H CHF2 0 H H H C6H5Cl H CHF2 0 H H H
Cl H CHF2 1 H H H CH3Cl H CHF2 1 H H H C2H5Cl H CHF2 1 H H H n-C3H7Cl H CHF2 1 H H H i-C3H7Cl H CHF2 1 H H H n-C4H9Cl H CHF2 1 H H H i-C4H9Cl H CHF2 1 H H H t-C4H9Cl H CHF2 1 H H H (CH2)3ClCl H CHF2 1 H H H CH2CNCl H CHF2 1 H H H CH2OCH3Cl H CHF2 1 H H H CH2CO2C2H5Cl H CHF2 1 H H H
Cl H CHF2 1 H H H
Cl H CHF2 1 H H H C6H5Cl H CHF2 1 H H H
Cl H CHF2 2 H H H CH3Cl H CHF2 2 H H H C2H5Cl H CHF2 2 H H H n-C3H7Cl H CHF2 2 H H H i-C3H7Cl H CHF2 2 H H H n-C4H9Cl H CHF2 2 H H H i-C4H9Cl H CHF2 2 H H H t-C4H9Cl H CHF2 2 H H H (CH2)3ClCl H CHF2 2 H H H CH2CNCl H CHF2 2 H H H CH2OCH3Cl H CHF2 2 H H H CH2CO2C2H5
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CHF2 2 H H H
Cl H CHF2 2 H H H
Cl H CHF2 2 H H H C6H5Cl H CHF2 2 H H H
Cl H CF3 0 H H H CH3Cl H CH2CH2F 0 H H H CH3Cl H CH2CH2F 0 H H H C2H5Cl H CH2CH2F 0 H H H n-C3H7Cl H CH2CH2F 0 H H H i-C3H7Cl H CH2CH2F 0 H H H n-C4H9Cl H CH2CH2F 0 H H H i-C4H9Cl H CH2CH2F 0 H H H t-C4H9Cl H CH2CH2F 0 H H H (CH2)3ClCl H CH2CH2F 0 H H H CH2CNCl H CH2CH2F 0 H H H CH2OCH3Cl H CH2CH2F 0 H H H CH2CO2C2H5Cl H CH2CH2F 0 H H H
Cl H CH2CH2F 0 H H H
Cl H CH2CH2F 0 H H H C6H5Cl H CH2CH2F 0 H H H
Cl H CH2CH2F 1 H H H CH3Cl H CH2CH2F 1 H H H C2H5Cl H CH2CH2F 1 H H H n-C3H7Cl H CH2CH2F 1 H H H i-C3H7Cl H CH2CH2F 1 H H H n-C4H9Cl H CH2CH2F 1 H H H i-C4H9Cl H CH2CH2F 1 H H H t-C4H9Cl H CH2CH2F 1 H H H (CH2)3ClCl H CH2CH2F 1 H H H CH2CNCl H CH2CH2F 1 H H H CH2OCH3Cl H CH2CH2F 1 H H H CH2CO2C2H5Cl H CH2CH2F 1 H H H
Cl H CH2CH2F 1 H H H
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH2CH2F 1 H H H C6H5Cl H CH2CH2F 1 H H H
Cl H CH2CH2F 2 H H H CH3Cl H CH2CH2F 2 H H H C2H5Cl H CH2CH2F 2 H H H n-C3H7Cl H CH2CH2F 2 H H H i-C3H7Cl H CH2CH2F 2 H H H n-C4H9Cl H CH2CH2F 2 H H H i-C4H9Cl H CH2CH2F 2 H H H t-C4H9Cl H CH2CH2F 2 H H H (CH2)3ClCl H CH2CH2F 2 H H H CH2CNCl H CH2CH2F 2 H H H CH2OCH3Cl H CH2CH2F 2 H H H CH2CO2C2H5Cl H CH2CH2F 2 H H H
Cl H CH2CH2F 2 H H H
Cl H CH2CH2F 2 H H H C6H5Cl H CH2CH2F 2 H H H
Cl H CH2CHF2 0 H H H CH3Cl H CH2CHF2 0 H H H C2H5Cl H CH2CHF2 0 H H H n-C3H7Cl H CH2CHF2 0 H H H i-C3H7Cl H CH2CHF2 0 H H H n-C4H9Cl H CH2CHF2 0 H H H i-C4H9Cl H CH2CHF2 0 H H H t-C4H9Cl H CH2CHF2 0 H H H (CH2)3ClCl H CH2CHF2 0 H H H CH2CNCl H CH2CHF2 0 H H H CH2OCH3Cl H CH2CHF2 0 H H H CH2CO2C2H5Cl H CH2CHF2 0 H H H
Cl H CH2CHF2 0 H H H
Cl H CH2CHF2 0 H H H C6H5Cl H CH2CHF2 0 H H H
Cl H CH2CHF2 1 H H H CH3Cl H CH2CHF2 1 H H H C2H5Cl H CH2CHF2 1 H H H n-C3H7
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH2CHF2 1 H H H i-C3H7Cl H CH2CHF2 1 H H H n-C4H9Cl H CH2CHF2 1 H H H i-C4H9Cl H CH2CHF2 1 H H H t-C4H9Cl H CH2CHF2 1 H H H (CH2)3ClCl H CH2CHF2 1 H H H CH2CNCl H CH2CHF2 1 H H H CH2OCH3Cl H CH2CHF2 1 H H H CH2CO2C2H5Cl H CH2CHF2 1 H H H
Cl H CH2CHF2 1 H H H
Cl H CH2CHF2 1 H H H C6H5Cl H CH2CHF2 1 H H H
Cl H CH2CHF2 2 H H H CH3Cl H CH2CHF2 2 H H H C2H5Cl H CH2CHF2 2 H H H n-C3H7Cl H CH2CHF2 2 H H H i-C3H7Cl H CH2CHF2 2 H H H n-C4H9Cl H CH2CHF2 2 H H H i-C4H9Cl H CH2CHF2 2 H H H t-C4H9Cl H CH2CHF2 2 H H H (CH2)3ClCl H CH2CHF2 2 H H H CH2CNCl H CH2CHF2 2 H H H CH2OCH3Cl H CH2CHF2 2 H H H CH2CO2C2H5Cl H CH2CHF2 2 H H H
Cl H CH2CHF2 2 H H H
Cl H CH2CHF2 2 H H H C6H5Cl H CH2CHF2 2 H H H
Cl H CH2CF3 0 H H H CH3Cl H CH2CF3 0 H H H C2H5Cl H CH2CF3 0 H H H n-C3H7Cl H CH2CF3 0 H H H i-C3H7Cl H CH2CF3 0 H H H n-C4H9Cl H CH2CF3 0 H H H i-C4H9Cl H CH2CF3 0 H H H t-C4H9Cl H CH2CF3 0 H H H (CH2)3Cl
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH2CF3 0 H H H CH2CNCl H CH2CF3 0 H H H CH2OCH3Cl H CH2CF3 0 H H H CH2CO2C2H5Cl H CH2CF3 0 H H H
Cl H CH2CF3 0 H H H
Cl H CH2CF3 0 H H H C6H5Cl H CH2CF3 0 H H H
Cl H CH2CF3 1 H H H CH3Cl H CH2CF3 1 H H H C2H5Cl H CH2CF3 1 H H H n-C3H7Cl H CH2CF3 1 H H H i-C3H7Cl H CH2CF3 1 H H H n-C4H9Cl H CH2CF3 1 H H H i-C4H9Cl H CH2CF3 1 H H H t-C4H9Cl H CH2CF3 1 H H H (CH2)3ClCl H CH2CF3 1 H H H CH2CNCl H CH2CF3 1 H H H CH2OCH3Cl H CH2CF3 1 H H H CH2CO2C2H5Cl H CH2CF3 1 H H H
Cl H CH2CF3 1 H H H
Cl H CH2CF3 1 H H H C6H5Cl H CH2CF3 1 H H H
Cl H CH2CF3 2 H H H CH3Cl H CH2CF3 2 H H H C2H5Cl H CH2CF3 2 H H H n-C3H7Cl H CH2CF3 2 H H H i-C3H7Cl H CH2CF3 2 H H H n-C4H9Cl H CH2CF3 2 H H H i-C4H9Cl H CH2CF3 2 H H H t-C4H9Cl H CH2CF3 2 H H H (CH2)3ClCl H CH2CF3 2 H H H CH2CNCl H CH2CF3 2 H H H CH2OCH3Cl H CH2CF3 2 H H H CH2CO2C2H5Cl H CH2CF3 2 H H H
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH2CF3 2 H H H
Cl H CH2CF3 2 H H H C6H5Cl H CH2CF3 2 H H H
Cl CH3 CH3 0 H H H CH3Cl CH3 CH3 1 H H H CH3Cl CH3 CH3 2 H H H CH3Br H CH3 0 H H H CH2OCH3Br H CH3 0 H H H CH2CO2C2H5Br H CH3 0 H H H CH3Br H CH3 0 H H H C2H5Br H CH3 0 H H H n-C3H7Br H CH3 0 H H H i-C3H7Br H CH3 0 H H H n-C4H9Br H CH3 0 H H H s-C4H9Br H CH3 0 H H H i-C4H9Br H CH3 0 H H H t-C4H9Br H CH3 0 H H H n-C5H11Br H CH3 0 H H H n-C6H13Br H CH3 0 H H H
Br H CH3 0 H H H
Br H CH3 0 H H H
Br H CH3 0 H H H
Br H CH3 0 H H H C6H5Br H CH3 0 H H H
Br H CH3 0 H H H
Br H CH3 0 H H H CH=CH2Br H CH3 0 H H H CH=CHCH3Br H CH3 0 H H H C(=CH2)CH3Br H CH3 0 H H H CH=CHC6H5Br H CH3 0 H H H
Br H CH3 0 H H H (CH2)4ClBr H CH3 0 H H H (CH2)3ClBr H CH3 0 H H H CH2CN
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH3 0 H H H CH2OC6H5Br H CH3 0 CH3 H H CH3Br H CH3 0 CH3 H H C2H5Br H CH3 0 CH3 H H n-C3H7Br H CH3 0 CH3 H H i-C3H7Br H CH3 0 CH3 H H n-C4H9Br H CH3 0 CH3 H H i-C4H9Br H CH3 0 CH3 H H s-C4H9Br H CH3 0 CH3 H H t-C4H9Br H CH3 0 CH3 H H (CH2)3ClBr H CH3 0 CH3 H H (CH2)4ClBr H CH3 0 CH3 H H CH2CNBr H CH3 0 CH3 H H CH2CO2C2H5Br H CH3 0 CH3 H H CH2OCH3Br H CH3 0 CH3 H H C6H5Br H CH3 0 CH3 H H
Br H CH3 0 C2H5 H H CH3Br H CH3 0 C2H5 H H C2H5Br H CH3 0 C2H5 H H n-C3H7Br H CH3 0 C2H5 H H i-C3H7Br H CH3 0 C2H5 H H n-C4H9Br H CH3 0 C2H5 H H i-C4H9Br H CH3 0 C2H5 H H s-C4H9Br H CH3 0 C2H5 H H t-C4H9Br H CH3 0 C2H5 H H (CH2)3ClBr H CH3 0 C2H5 H H (CH2)4ClBr H CH3 0 C2H5 H H CH2CNBr H CH3 0 C2H5 H H CH2CO2C2H5Br H CH3 0 C2H5 H H CH2OCH3Br H CH3 0 C2H5 H H C6H5Br H CH3 0 C2H5 H H
Br H CH3 0 n-C3H7 H H CH3Br H CH3 0 n-C3H7 H H C2H5Br H CH3 0 n-C3H7 H H n-C3H7Br H CH3 0 n-C3H7 H H i-C3H7Br H CH3 0 n-C3H7 H H n-C4H9Br H CH3 0 n-C3H7 H H i-C4H9Br H CH3 0 n-C3H7 H H s-C4H9Br H CH3 0 n-C3H7 H H t-C4H9Br H CH3 0 n-C3H7 H H (CH2)3ClBr H CH3 0 n-C3H7 H H (CH2)4Cl
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH3 0 n-C3H7 H H CH2CNBr H CH3 0 n-C3H7 H H CH2CO2C2H5Br H CH3 0 n-C3H7 H H CH2OCH3Br H CH3 0 n-C3H7 H H C6H5Br H CH3 0 n-C3H7 H H
Br H CH3 0 i-C3H7 H H CH3Br H CH3 0 i-C3H7 H H C2H5Br H CH3 0 i-C3H7 H H n-C3H7Br H CH3 0 i-C3H7 H H i-C3H7Br H CH3 0 i-C3H7 H H n-C4H9Br H CH3 0 i-C3H7 H H i-C4H9Br H CH3 0 i-C3H7 H H s-C4H9Br H CH3 0 i-C3H7 H H t-C4H9Br H CH3 0 i-C3H7 H H (CH2)3ClBr H CH3 0 i-C3H7 H H (CH2)4ClBr H CH3 0 i-C3H7 H H CH2CNBr H CH3 0 i-C3H7 H H CH2CO2C2H5Br H CH3 0 i-C3H7 H H CH2OCH3Br H CH3 0 i-C3H7 H H C6H5Br H CH3 0 i-C3H7 H H
Br H CH3 0 CH2OCH3 H H CH3Br H CH3 0 CH2OCH3 H H C6H5Br H CH3 0 CH2OC2H5 H H CH3Br H CH3 0 CH2OC2H5 H H C6H5Br H CH3 1 H H H CH3Br H CH3 1 H H H C2H5Br H CH3 1 H H H n-C3H7Br H CH3 1 H H H i-C3H7Br H CH3 1 H H H n-C4H9Br H CH3 1 H H H i-C4H9Br H CH3 1 H H H t-C4H9Br H CH3 1 H H H (CH2)3ClBr H CH3 1 H H H CH2CNBr H CH3 1 H H H CH2OCH3Br H CH3 1 H H H CH2CO2C2H5Br H CH3 1 H H H
Br H CH3 1 H H H
Br H CH3 1 H H H C6H5
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH3 1 H H H
Br H CH3 1 CH3 H H CH3Br H CH3 1 CH3 H H C2H5Br H CH3 1 CH3 H H n-C3H7Br H CH3 1 CH3 H H i-C3H7Br H CH3 1 CH3 H H n-C4H9Br H CH3 1 CH3 H H i-C4H9Br H CH3 1 CH3 H H s-C4H9Br H CH3 1 CH4 H H t-C4H9Br H CH3 1 CH3 H H (CH2)3ClBr H CH3 1 CH3 H H (CH2)4ClBr H CH4 1 CH3 H H CH2CNBr H CH3 1 CH3 H H CH2OCH3Br H CH3 1 CH4 H H CH2CO2C2H5Br H CH3 1 CH3 H H C6H5Br H CH3 1 CH3 H H
Br H CH3 1 C2H5 H H CH3Br H CH3 1 C2H5 H H C2H5Br H CH3 1 C2H5 H H n-C3H7Br H CH3 1 C2H5 H H i-C3H7Br H CH3 1 C2H5 H H n-C4H9Br H CH3 1 C2H5 H H i-C4H9Br H CH3 1 C2H5 H H s-C4H9Br H CH3 1 C2H5 H H t-C4H9Br H CH3 1 C2H5 H H (CH2)3ClBr H CH3 1 C2H5 H H (CH2)4ClBr H CH3 1 C2H5 H H CH2CNBr H CH3 1 C2H5 H H CH2CO2C2H5Br H CH3 1 C2H5 H H CH2OCH3Br H CH3 1 C2H5 H H C6H5Br H CH3 1 C2H5 H H
Br H CH3 1 n-C3H7 H H CH3Br H CH3 1 n-C3H7 H H C2H5Br H CH3 1 n-C3H7 H H n-C3H7Br H CH3 1 n-C3H7 H H i-C3H7Br H CH3 1 n-C3H7 H H n-C4H9Br H CH3 1 n-C3H7 H H i-C4H9Br H CH3 1 n-C3H7 H H s-C4H9Br H CH3 1 n-C3H7 H H t-C4H9Br H CH3 1 n-C3H7 H H (CH2)3Cl
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH3 1 n-C3H7 H H (CH2)4ClBr H CH3 1 n-C3H7 H H CH2CNBr H CH3 1 n-C3H7 H H CH2CO2C2H5Br H CH3 1 n-C3H7 H H CH2OCH3Br H CH3 1 n-C3H7 H H C6H5Br H CH3 1 n-C3H7 H H
Br H CH3 1 i-C3H7 H H CH3Br H CH3 1 i-C3H7 H H C2H5Br H CH3 1 i-C3H7 H H n-C3H7Br H CH3 1 i-C3H7 H H i-C3H7Br H CH3 1 i-C3H7 H H n-C4H9Br H CH3 1 i-C3H7 H H i-C4H9Br H CH3 1 i-C3H7 H H s-C4H9Br H CH3 1 i-C3H7 H H t-C4H9Br H CH3 1 i-C3H7 H H (CH2)3ClBr H CH3 1 i-C3H7 H H (CH2)4ClBr H CH3 1 i-C3H7 H H CH2CNBr H CH3 1 i-C3H7 H H CH2CO2C2H5Br H CH3 1 i-C3H7 H H CH2OCH3Br H CH3 1 i-C3H7 H H C6H5Br H CH3 1 i-C3H7 H H
Br H CH3 2 H H H CH3Br H CH3 2 H H H C2H5Br H CH3 2 H H H n-C3H7Br H CH3 2 H H H i-C3H7Br H CH3 2 H H H n-C4H9Br H CH3 2 H H H i-C4H9Br H CH3 2 H H H t-C4H9Br H CH3 2 H H H (CH2)3ClBr H CH3 2 H H H CH2CNBr H CH3 2 H H H CH2OCH3Br H CH3 2 H H H CH2CO2C2H5Br H CH3 2 H H H
Br H CH3 2 H H H
Br H CH3 2 H H H C6H5Br H CH3 2 H H H
Br H CH3 2 CH3 H H CH3
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH3 2 CH3 H H C2H5Br H CH3 2 CH3 H H n-C3H7Br H CH3 2 CH3 H H i-C3H7Br H CH3 2 CH3 H H n-C4H9Br H CH3 2 CH3 H H i-C4H9Br H CH3 2 CH3 H H s-C4H9Br H CH3 2 CH3 H H t-C4H9Br H CH3 2 CH3 H H (CH2)3ClBr H CH3 2 CH3 H H (CH2)4ClBr H CH3 2 CH3 H H C6H5Br H CH3 2 CH3 H H
Br H CH3 2 C2H5 H H CH3Br H CH3 2 C2H5 H H C2H5Br H CH3 2 C2H5 H H n-C3H7Br H CH3 2 C2H5 H H i-C3H7Br H CH3 2 CH3 H H CH2CNBr H CH3 2 CH3 H H CH2CO2C2H5Br H CH3 2 CH3 H H CH2OCH3Br H CH3 2 C2H5 H H n-C4H9Br H CH3 2 C2H5 H H i-C4H9Br H CH3 2 C2H5 H H s-C4H9Br H CH3 2 C2H5 H H t-C4H9Br H CH3 2 C2H5 H H (CH2)3ClBr H CH3 2 C2H5 H H (CH2)4ClBr H CH3 2 C2H5 H H CH2CNBr H CH3 2 C2H5 H H CH2CO2C2H5Br H CH3 2 C2H5 H H CH2OCH3Br H CH3 2 C2H5 H H C6H5Br H CH3 2 C2H5 H H
Br H CH3 2 n-C3H7 H H CH3Br H CH3 2 n-C3H7 H H C2H5Br H CH3 2 n-C3H7 H H n-C3H7Br H CH3 2 n-C3H7 H H i-C3H7Br H CH3 2 n-C3H7 H H n-C4H9Br H CH3 2 n-C3H7 H H i-C4H9Br H CH3 2 n-C3H7 H H s-C4H9Br H CH3 2 n-C3H7 H H t-C4H9Br H CH3 2 n-C3H7 H H (CH2)3ClBr H CH3 2 n-C3H7 H H (CH2)4ClBr H CH3 2 n-C3H7 H H CH2CNBr H CH3 2 n-C3H7 H H CH2CO2C2H5
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH3 2 n-C3H7 H H CH2OCH3Br H CH3 2 n-C3H7 H H C6H5Br H CH3 2 n-C3H7 H H
Br H CH3 2 i-C3H7 H H CH3Br H CH3 2 i-C3H7 H H C2H5Br H CH3 2 i-C3H7 H H n-C3H7Br H CH3 2 i-C3H7 H H i-C3H7Br H CH3 2 i-C3H7 H H n-C4H9Br H CH3 2 i-C3H7 H H i-C4H9Br H CH3 2 i-C3H7 H H s-C4H9Br H CH3 2 i-C3H7 H H t-C4H9Br H CH3 2 i-C3H7 H H (CH2)3ClBr H CH3 2 i-C3H7 H H (CH2)4ClBr H CH3 2 i-C3H7 H H CH2CNBr H CH3 2 i-C3H7 H H CH2CO2C2H5Br H CH3 2 i-C3H7 H H CH2OCH3Br H CH3 2 i-C3H7 H H C6H5Br H CH3 2 i-C3H7 H H
Br H C2H5 0 H H H CH3Br H C2H5 0 H H H C2H5Br H C2H5 0 H H H n-C3H7Br H C2H5 0 H H H i-C3H7Br H C2H5 0 H H H n-C4H9Br H C2H5 0 H H H i-C4H9Br H C2H5 0 H H H s-C4H9Br H C2H5 0 H H H t-C4H9Br H C2H5 0 H H H n-C5H11Br H C2H5 0 H H H n-C6H13Br H C2H5 0 H H H (CH2)4ClBr H C2H5 0 H H H (CH2)3ClBr H C2H5 0 H H H CH2CNBr H C2H5 0 H H H
Br H C2H5 0 H H H
Br H C2H5 0 CH3 H H CH3Br H C2H5 0 CH3 H H C2H5Br H C2H5 0 CH3 H H n-C3H7Br H C2H5 0 CH3 H H i-C3H7Br H C2H5 0 CH3 H H n-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H C2H5 0 CH3 H H i-C4H9Br H C2H5 0 CH3 H H s-C4H9Br H C2H5 0 CH3 H H t-C4H9Br H C2H5 0 CH3 H H (CH2)3ClBr H C2H5 0 CH3 H H (CH2)4ClBr H C2H5 0 CH3 H H CH2CNBr H C2H5 0 CH3 H H CH2CO2C2H5Br H C2H5 0 CH3 H H CH2OCH3Br H C2H5 0 CH3 H H C6H5Br H C2H5 0 CH3 H H
Br H C2H5 0 C2H5 H H CH3Br H C2H5 0 C2H5 H H C2H5Br H C2H5 0 C2H5 H H n-C3H7Br H C2H5 0 C2H5 H H i-C3H7Br H C2H5 0 C2H5 H H n-C4H9Br H C2H5 0 C2H5 H H i-C4H9Br H C2H5 0 C2H5 H H s-C4H9Br H C2H5 0 C2H5 H H t-C4H9Br H C2H5 0 C2H5 H H (CH2)3ClBr H C2H5 0 C2H5 H H (CH2)4ClBr H C2H5 0 C2H5 H H CH2CNBr H C2H5 0 C2H5 H H CH2CO2C2H5Br H C2H5 0 C2H5 H H CH2OCH3Br H C2H5 0 C2H5 H H C6H5Br H C2H5 0 C2H5 H H
Br H C2H5 0 n-C3H7 H H CH3Br H C2H5 0 n-C3H7 H H C2H5Br H C2H5 0 n-C3H7 H H n-C3H7Br H C2H5 0 n-C3H7 H H i-C3H7Br H C2H5 0 n-C3H7 H H n-C4H9Br H C2H5 0 n-C3H7 H H i-C4H9Br H C2H5 0 n-C3H7 H H s-C4H9Br H C2H5 0 n-C3H7 H H t-C4H9Br H C2H5 0 n-C3H7 H H (CH2)3ClBr H C2H5 0 n-C3H7 H H (CH2)4ClBr H C2H5 0 n-C3H7 H H CH2CNBr H C2H5 0 n-C3H7 H H CH2CO2C2H5Br H C2H5 0 n-C3H7 H H CH2OCH3Br H C2H5 0 n-C3H7 H H C6H5Br H C2H5 0 n-C3H7 H H
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H C2H5 0 i-C3H7 H H CH3Br H C2H5 0 i-C3H7 H H C2H5Br H C2H5 0 i-C3H7 H H n-C3H7Br H C2H5 0 i-C3H7 H H i-C3H7Br H C2H5 0 i-C3H7 H H n-C4H9Br H C2H5 0 i-C3H7 H H i-C4H9Br H C2H5 0 i-C3H7 H H s-C4H9Br H C2H5 0 i-C3H7 H H t-C4H9Br H C2H5 0 i-C3H7 H H (CH2)3ClBr H C2H5 0 i-C3H7 H H (CH2)4ClBr H C2H5 0 i-C3H7 H H CH2CNBr H C2H5 0 i-C3H7 H H CH2CO2C2H5Br H C2H5 0 i-C3H7 H H CH2OCH3Br H C2H5 0 i-C3H7 H H C6H5Br H C2H5 0 i-C3H7 H H
Br H C2H5 0 CH2OCH3 H H CH3Br H C2H5 0 CH2SCH3 H H CH3Br H C2H5 1 H H H CH3Br H C2H5 1 H H H C2H5Br H C2H5 1 H H H n-C3H7Br H C2H5 1 H H H n-C4H9Br H C2H5 1 H H H i-C4H9Br H C2H5 1 H H H t-C4H9Br H C2H5 1 H H H (CH2)3ClBr H C2H5 1 H H H CH2CNBr H C2H5 1 H H H CH2OCH3Br H C2H5 1 H H H CH2CO2C2H5Br H C2H5 1 H H H
Br H C2H5 1 H H H
Br H C2H5 1 H H H C6H5Br H C2H5 1 H H H
Br H C2H5 1 CH3 H H CH3Br H C2H5 1 CH3 H H C2H5Br H C2H5 1 CH3 H H n-C3H7Br H C2H5 1 CH3 H H i-C3H7Br H C2H5 1 CH3 H H n-C4H9Br H C2H5 1 CH3 H H i-C4H9Br H C2H5 1 CH3 H H s-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H C2H5 1 CH3 H H t-C4H9Br H C2H5 1 CH3 H H (CH2)3ClBr H C2H5 1 CH3 H H (CH2)4ClBr H C2H5 1 CH3 H H CH2CNBr H C2H5 1 CH3 H H CH2CO2C2H5Br H C2H5 1 CH3 H H CH2OCH3Br H C2H5 1 CH3 H H C6H5Br H C2H5 1 CH3 H H
Br H C2H5 1 C2H5 H H CH3Br H C2H5 1 C2H5 H H C2H5Br H C2H5 1 C2H5 H H n-C3H7Br H C2H5 1 C2H5 H H i-C3H7Br H C2H5 1 C2H5 H H n-C4H9Br H C2H5 1 C2H5 H H i-C4H9Br H C2H5 1 C2H5 H H s-C4H9Br H C2H5 1 C2H5 H H t-C4H9Br H C2H5 1 C2H5 H H (CH2)3ClBr H C2H5 1 C2H5 H H (CH2)4ClBr H C2H5 1 C2H5 H H CH2CNBr H C2H5 1 C2H5 H H CH2CO2C2H5Br H C2H5 1 C2H5 H H CH2OCH3Br H C2H5 1 C2H5 H H C6H5Br H C2H5 1 C2H5 H H
Br H C2H5 1 n-C3H7 H H CH3Br H C2H5 1 n-C3H7 H H C2H5Br H C2H5 1 n-C3H7 H H n-C3H7Br H C2H5 1 n-C3H7 H H i-C3H7Br H C2H5 1 n-C3H7 H H n-C4H9Br H C2H5 1 n-C3H7 H H i-C4H9Br H C2H5 1 n-C3H7 H H s-C4H9Br H C2H5 1 n-C3H7 H H t-C4H9Br H C2H5 1 n-C3H7 H H (CH2)3ClBr H C2H5 1 n-C3H7 H H (CH2)4ClBr H C2H5 1 n-C3H7 H H CH2CNBr H C2H5 1 n-C3H7 H H CH2CO2C2H5Br H C2H5 1 n-C3H7 H H CH2OCH3Br H C2H5 1 n-C3H7 H H C6H5Br H C2H5 1 n-C3H7 H H
Br H C2H5 1 i-C3H7 H H CH3Br H C2H5 1 i-C3H7 H H C2H5
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H C2H5 1 i-C3H7 H H n-C3H7Br H C2H5 1 i-C3H7 H H i-C3H7Br H C2H5 1 i-C3H7 H H n-C4H9Br H C2H5 1 i-C3H7 H H i-C4H9Br H C2H5 1 i-C3H7 H H s-C4H9Br H C2H5 1 i-C3H7 H H t-C4H9Br H C2H5 1 i-C3H7 H H (CH2)3ClBr H C2H5 1 i-C3H7 H H (CH2)4ClBr H C2H5 1 i-C3H7 H H CH2CNBr H C2H5 1 i-C3H7 H H CH2CO2C2H5Br H C2H5 1 i-C3H7 H H CH2OCH3Br H C2H5 1 i-C3H7 H H C6H5Br H C2H5 1 i-C3H7 H H
Br H C2H5 2 H H H CH3Br H C2H5 2 H H H C2H5Br H C2H5 2 H H H n-C3H7Br H C2H5 2 H H H n-C4H9Br H C2H5 2 H H H i-C4H9Br H C2H5 2 H H H t-C4H9Br H C2H5 2 H H H (CH2)3ClBr H C2H5 2 H H H CH2CNBr H C2H5 2 H H H CH2OCH3Br H C2H5 2 H H H CH2CO2C2H5Br H C2H5 2 H H H
Br H C2H5 2 H H H
Br H C2H5 2 H H H C6H5Br H C2H5 2 H H H
Br H C2H5 2 CH3 H H CH3Br H C2H5 2 CH3 H H C2H5Br H C2H5 2 CH3 H H n-C3H7Br H C2H5 2 CH3 H H i-C3H7Br H C2H5 2 CH3 H H n-C4H9Br H C2H5 2 CH3 H H i-C4H9Br H C2H5 2 CH3 H H s-C4H9Br H C2H5 2 CH3 H H t-C4H9Br H C2H5 2 CH3 H H (CH2)3ClBr H C2H5 2 CH3 H H (CH2)4ClBr H C2H5 2 CH3 H H CH2CN
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H C2H5 2 CH3 H H CH2CO2C2H5Br H C2H5 2 CH3 H H CH2OCH3Br H C2H5 2 CH3 H H C6H5Br H C2H5 2 CH3 H H
Br H C2H5 2 C2H5 H H CH3Br H C2H5 2 C2H5 H H C2H5Br H C2H5 2 C2H5 H H n-C3H7Br H C2H5 2 C2H5 H H i-C3H7Br H C2H5 2 C2H5 H H n-C4H9Br H C2H5 2 C2H5 H H i-C4H9Br H C2H5 2 C2H5 H H s-C4H9Br H C2H5 2 C2H5 H H t-C4H9Br H C2H5 2 C2H5 H H (CH2)3ClBr H C2H5 2 C2H5 H H (CH2)4ClBr H C2H5 2 C2H5 H H CH2CNBr H C2H5 2 C2H5 H H CH2CO2C2H5Br H C2H5 2 C2H5 H H CH2OCH3Br H C2H5 2 C2H5 H H C6H5Br H C2H5 2 C2H5 H H
Br H C2H5 2 n-C3H7 H H CH3Br H C2H5 2 n-C3H7 H H C2H5Br H C2H5 2 n-C3H7 H H n-C3H7Br H C2H5 2 n-C3H7 H H i-C3H7Br H C2H5 2 n-C3H7 H H n-C4H9Br H C2H5 2 n-C3H7 H H i-C4H9Br H C2H5 2 n-C3H7 H H s-C4H9Br H C2H5 2 n-C3H7 H H t-C4H9Br H C2H5 2 n-C3H7 H H (CH2)3ClBr H C2H5 2 n-C3H7 H H (CH2)4ClBr H C2H5 2 n-C3H7 H H CH2CNBr H C2H5 2 n-C3H7 H H CH2CO2C2H5Br H C2H5 2 n-C3H7 H H CH2OCH3Br H C2H5 2 n-C3H7 H H C6H5Br H C2H5 2 n-C3H7 H H
Br H C2H5 2 i-C3H7 H H CH3Br H C2H5 2 i-C3H7 H H C2H5Br H C2H5 2 i-C3H7 H H n-C3H7Br H C2H5 2 i-C3H7 H H i-C3H7Br H C2H5 2 i-C3H7 H H n-C4H9Br H C2H5 2 i-C3H7 H H i-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H C2H5 2 i-C3H7 H H s-C4H9Br H C2H5 2 i-C3H7 H H t-C4H9Br H C2H5 2 i-C3H7 H H (CH2)3ClBr H C2H5 2 i-C3H7 H H (CH2)4ClBr H C2H5 2 i-C3H7 H H CH2CNBr H C2H5 2 i-C3H7 H H CH2CO2C2H5Br H C2H5 2 i-C3H7 H H CH2OCH3Br H C2H5 2 i-C3H7 H H C6H5Br H C2H5 2 i-C3H7 H H
Br H n-C3H7 0 H H H CH3Br H n-C3H7 0 H H H C2H5Br H n-C3H7 0 H H H n-C3H7Br H n-C3H7 0 H H H n-C4H9Br H n-C3H7 0 H H H i-C4H9Br H n-C3H7 0 H H H t-C4H9Br H n-C3H7 0 H H H (CH2)3ClBr H n-C3H7 0 H H H CH2CNBr H n-C3H7 0 H H H CH2OCH3Br H n-C3H7 0 H H H CH2CO2C2H5Br H n-C3H7 0 H H H
Br H n-C3H7 0 H H H
Br H n-C3H7 0 H H H C6H5Br H n-C3H7 0 H H H
Br H n-C3H7 1 H H H CH3Br H n-C3H7 1 H H H C2H5Br H n-C3H7 1 H H H n-C3H7Br H n-C3H7 1 H H H n-C4H9Br H n-C3H7 1 H H H i-C4H9Br H n-C3H7 1 H H H t-C4H9Br H n-C3H7 1 H H H (CH2)3ClBr H n-C3H7 1 H H H CH2CNBr H n-C3H7 1 H H H CH2OCH3Br H n-C3H7 1 H H H CH2CO2C2H5Br H n-C3H7 1 H H H
Br H n-C3H7 1 H H H
Br H n-C3H7 1 H H H C6H5
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H n-C3H7 1 H H H
Br H n-C3H7 2 H H H CH3Br H n-C3H7 2 H H H C2H5Br H n-C3H7 2 H H H n-C3H7Br H n-C3H7 2 H H H n-C4H9Br H n-C3H7 2 H H H i-C4H9Br H n-C3H7 2 H H H t-C4H9Br H n-C3H7 2 H H H (CH2)3ClBr H n-C3H7 2 H H H CH2CNBr H n-C3H7 2 H H H CH2OCH3Br H n-C3H7 2 H H H CH2CO2C2H5Br H n-C3H7 2 H H H
Br H n-C3H7 2 H H H
Br H n-C3H7 2 H H H C6H5Br H n-C3H7 2 H H H
Br H CHF2 0 H H H CH3Br H CHF2 0 H H H C2H5Br H CHF2 0 H H H n-C3H7Br H CHF2 0 H H H n-C4H9Br H CHF2 0 H H H i-C4H9Br H CHF2 0 H H H t-C4H9Br H CHF2 0 H H H (CH2)3ClBr H CHF2 0 H H H CH2CNBr H CHF2 0 H H H CH2OCH3Br H CHF2 0 H H H CH2CO2C2H5Br H CHF2 0 H H H
Br H CHF2 0 H H H
Br H CHF2 0 H H H C6H5Br H CHF2 0 H H H
Br H CHF2 1 H H H CH3Br H CHF2 1 H H H C2H5Br H CHF2 1 H H H n-C3H7Br H CHF2 1 H H H n-C4H9Br H CHF2 1 H H H i-C4H9Br H CHF2 1 H H H t-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CHF2 1 H H H (CH2)3ClBr H CHF2 1 H H H CH2CNBr H CHF2 1 H H H CH2OCH3Br H CHF2 1 H H H CH2CO2C2H5Br H CHF2 1 H H H
Br H CHF2 1 H H H
Br H CHF2 1 H H H C6H5Br H CHF2 1 H H H
Br H CHF2 2 H H H CH3Br H CHF2 2 H H H C2H5Br H CHF2 2 H H H n-C3H7Br H CHF2 2 H H H n-C4H9Br H CHF2 2 H H H i-C4H9Br H CHF2 2 H H H t-C4H9Br H CHF2 2 H H H (CH2)3ClBr H CHF2 2 H H H CH2CNBr H CHF2 2 H H H CH2OCH3Br H CHF2 2 H H H CH2CO2C2H5Br H CHF2 2 H H H
Br H CHF2 2 H H H
Br H CHF2 2 H H H C6H5Br H CHF2 2 H H H
Br H CF3 0 H H H C6H5Br H CF3 0 H H H CH3Br H CH2CH2F 0 H H H CH3Br H CH2CH2F 0 H H H C2H5Br H CH2CH2F 0 H H H n-C3H7Br H CH2CH2F 0 H H H i-C3H7Br H CH2CH2F 0 H H H n-C4H9Br H CH2CH2F 0 H H H i-C4H9Br H CH2CH2F 0 H H H t-C4H9Br H CH2CH2F 0 H H H (CH2)3ClBr H CH2CH2F 0 H H H CH2CNBr H CH2CH2F 0 H H H CH2OCH3Br H CH2CH2F 0 H H H CH2CO2C2H5Br H CH2CH2F 0 H H H
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH2CH2F 0 H H H
Br H CH2CH2F 0 H H H C6H5Br H CH2CH2F 0 H H H
Br H CH2CH2F 1 H H H CH3Br H CH2CH2F 1 H H H C2H5Br H CH2CH2F 1 H H H n-C3H7Br H CH2CH2F 1 H H H i-C3H7Br H CH2CH2F 1 H H H n-C4H9Br H CH2CH2F 1 H H H i-C4H9Br H CH2CH2F 1 H H H t-C4H9Br H CH2CH2F 1 H H H (CH2)3ClBr H CH2CH2F 1 H H H CH2CNBr H CH2CH2F 1 H H H CH2OCH3Br H CH2CH2F 1 H H H CH2CO2C2H5Br H CH2CH2F 1 H H H
Br H CH2CH2F 1 H H H
Br H CH2CH2F 1 H H H C6H5Br H CH2CH2F 1 H H H
Br H CH2CH2F 2 H H H CH3Br H CH2CH2F 2 H H H C2H5Br H CH2CH2F 2 H H H n-C3H7Br H CH2CH2F 2 H H H i-C3H7Br H CH2CH2F 2 H H H n-C4H9Br H CH2CH2F 2 H H H i-C4H9Br H CH2CH2F 2 H H H t-C4H9Br H CH2CH2F 2 H H H (CH2)3ClBr H CH2CH2F 2 H H H CH2CNBr H CH2CH2F 2 H H H CH2OCH3Br H CH2CH2F 2 H H H CH2CO2C2H5Br H CH2CH2F 2 H H H
Br H CH2CH2F 2 H H H
Br H CH2CH2F 2 H H H C6H5Br H CH2CH2F 2 H H H
Br H CH2CHF2 0 H H H CH3
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH2CHF2 0 H H H C2H5Br H CH2CHF2 0 H H H n-C3H7Br H CH2CHF2 0 H H H i-C3H7Br H CH2CHF2 0 H H H n-C4H9Br H CH2CHF2 0 H H H i-C4H9Br H CH2CHF2 0 H H H t-C4H9Br H CH2CHF2 0 H H H (CH2)3ClBr H CH2CHF2 0 H H H CH2CNBr H CH2CHF2 0 H H H CH2OCH3Br H CH2CHF2 0 H H H CH2CO2C2H5Br H CH2CHF2 0 H H H
Br H CH2CHF2 0 H H H
Br H CH2CHF2 0 H H H C6H5Br H CH2CHF2 0 H H H
Br H CH2CHF2 1 H H H CH3Br H CH2CHF2 1 H H H C2H5Br H CH2CHF2 1 H H H n-C3H7Br H CH2CHF2 1 H H H i-C3H7Br H CH2CHF2 1 H H H n-C4H9Br H CH2CHF2 1 H H H i-C4H9Br H CH2CHF2 1 H H H t-C4H9Br H CH2CHF2 1 H H H (CH2)3ClBr H CH2CHF2 1 H H H CH2CNBr H CH2CHF2 1 H H H CH2OCH3Br H CH2CHF2 1 H H H CH2CO2C2H5Br H CH2CHF2 1 H H H
Br H CH2CHF2 1 H H H
Br H CH2CHF2 1 H H H C6H5Br H CH2CHF2 1 H H H
Br H CH2CHF2 2 H H H CH3Br H CH2CHF2 2 H H H C2H5Br H CH2CHF2 2 H H H n-C3H7Br H CH2CHF2 2 H H H i-C3H7Br H CH2CHF2 2 H H H n-C4H9Br H CH2CHF2 2 H H H i-C4H9Br H CH2CHF2 2 H H H t-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH2CHF2 2 H H H (CH2)3ClBr H CH2CHF2 2 H H H CH2CNBr H CH2CHF2 2 H H H CH2OCH3Br H CH2CHF2 2 H H H CH2CO2C2H5Br H CH2CHF2 2 H H H
Br H CH2CHF2 2 H H H
Br H CH2CHF2 2 H H H C6H5Br H CH2CHF2 2 H H H
Br H CH2CF3 0 H H H CH3Br H CH2CF3 0 H H H C2H5Br H CH2CF3 0 H H H n-C3H7Br H CH2CF3 0 H H H i-C3H7Br H CH2CF3 0 H H H n-C4H9Br H CH2CF3 0 H H H i-C4H9Br H CH2CF3 0 H H H t-C4H9Br H CH2CF3 0 H H H (CH2)3ClBr H CH2CF3 0 H H H CH2CNBr H CH2CF3 0 H H H CH2OCH3Br H CH2CF3 0 H H H CH2CO2C2H5Br H CH2CF3 0 H H H
Br H CH2CF3 0 H H H
Br H CH2CF3 0 H H H C6H5Br H CH2CF3 0 H H H
Br H CH2CF3 1 H H H CH3Br H CH2CF3 1 H H H C2H5Br H CH2CF3 1 H H H n-C3H7Br H CH2CF3 1 H H H i-C3H7Br H CH2CF3 1 H H H n-C4H9Br H CH2CF3 1 H H H i-C4H9Br H CH2CF3 1 H H H t-C4H9Br H CH2CF3 1 H H H (CH2)3ClBr H CH2CF3 1 H H H CH2CNBr H CH2CF3 1 H H H CH2OCH3Br H CH2CF3 1 H H H CH2CO2C2H5Br H CH2CF3 1 H H H
表2(续)R1 R2 R3 n R5 R6 R7 R8Br H CH2CF3 1 H H H
Br H CH2CF3 1 H H H C6H5Br H CH2CF3 1 H H H
Br H CH2CF3 2 H H H CH3Br H CH2CF3 2 H H H C2H5Br H CH2CF3 2 H H H n-C3H7Br H CH2CF3 2 H H H i-C3H7Br H CH2CF3 2 H H H n-C4H9Br H CH2CF3 2 H H H i-C4H9Br H CH2CF3 2 H H H t-C4H9Br H CH2CF3 2 H H H (CH2)3ClBr H CH2CF3 2 H H H CH2CNBr H CH2CF3 2 H H H CH2OCH3Br H CH2CF3 2 H H H CH2CO2C2H5Br H CH2CF3 2 H H H
Br H CH2CF3 2 H H H
Br H CH2CF3 2 H H H C6H5Br H CH2CF3 2 H H H
I H C2H5 0 H H H C6H5I H CH3 0 H H H CH3I H CH3 0 H H H C2H5I H CH3 0 H H H n-C3H7I H CH3 0 H H H i-C3H7I H CH3 0 H H H n-C4H9I H CH3 2 H H H C2H5I H CH3 1 H H H C2H5Cl H CH3 0 H H H COCH3Cl H CH3 1 H H H COCH3Cl H CH3 2 H H H COCH3Cl H C2H5 0 H H H COCH3Cl H CH3 0 H H H CO2CH3Cl H CH3 1 H H H CO2CH3Cl H CH3 2 H H H CO2CH3Cl H C2H5 0 H H H CO2CH3Cl H C2H5 1 H H H CO2CH3Cl H C2H5 2 H H H CO2CH3
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 0 H H H CO2C2H5Cl H CH3 1 H H H CO2C2H5Cl H CH3 2 H H H CO2C2H5Cl H C2H5 0 H H H CO2C2H5Cl H C2H5 1 H H H CO2C2H5Cl H C2H5 2 H H H CO2C2H5Br H C2H5 0 H H H
Br H C2H5 0 H H H
Br H C2H5 0 H H H C6H5Br H C2H5 0 H H H CH2CO2C2H5Br H C2H5 0 H H H CH2OCH3Br H C2H5 0 H H H
Br H C2H5 1 H H H i-C3H7Br H C2H5 1 H H H s-C4H9Br H C2H5 2 H H H i-C3H7Br H C2H5 2 H H H s-C4H9Br H CH3 1 H H H s-C4H9Br H CH3 2 H H H s-C4H9Cl H C2H5 0 C2H5 H H
Cl H C2H5 0 C2H5 H H COCH3Cl H C2H5 0 C2H5 H H CO2C2H5Cl H C2H5 0 C2H5 H H CO2CH3Cl H C2H5 0 CH2OC2H5 H H C2H5Cl H C2H5 0 CH2OC2H5 H H CH2OCH3Cl H C2H5 0 CH2OC2H5 H H n-C3H7Cl H C2H5 0 CH2OC2H5 H H n-C4H9Cl H C2H5 0 CH2OC2H5 H H t-C4H9Cl H C2H5 0 CH2OCH3 H H C2H5Cl H C2H5 0 CH2OCH3 H H CH2OCH3Cl H C2H5 0 CH2OCH3 H H n-C3H7Cl H C2H5 0 CH2OCH3 H H n-C4H9Cl H C2H5 0 CH2OCH3 H H t-C4H9Cl H C2H5 0 CH2SCH3 H H C2H5Cl H C2H5 0 CH2SCH3 H H CH2OCH3Cl H C2H5 0 CH2SCH3 H H n-C3H7Cl H C2H5 0 CH2SCH3 H H n-C4H9Cl H C2H5 0 CH2SCH3 H H t-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 0 CH3 H H
Cl H C2H5 0 CH3 H H COCH3Cl H C2H5 0 CH3 H H CO2C2H5Cl H C2H5 0 CH3 H H CO2CH3Cl H C2H5 0 COC2H5 H H CH2OCH3Cl H C2H5 0 COC2H5 H H n-C3H7Cl H C2H5 0 COC2H5 H H n-C4H9Cl H C2H5 0 COC2H5 H H t-C4H9Cl H C2H5 0 COC3H7-n H H C2H5Cl H C2H5 0 COC3H7-n H H CH2OCH3Cl H C2H5 0 COC3H7-n H H n-C3H7Cl H C2H5 0 COC3H7-n H H n-C4H9Cl H C2H5 0 COC3H7-n H H t-C4H9Cl H C2H5 0 COCH3 H H C2H5Cl H C2H5 0 COCH3 H H CH2OCH3Cl H C2H5 0 COCH3 H H CH3Cl H C2H5 0 COCH3 H H n-C3H7Cl H C2H5 0 COCH3 H H n-C4H9Cl H C2H5 0 COCH3 H H t-C4H9Cl H C2H5 0 H H H (CH2)5BrCl H C2H5 0 H H H CH2CH2CO2HCl H C2H5 0 H H H CH2CH2SCH3Cl H C2H5 0 H H H CO2C2H5Cl H C2H5 0 H H H CO2CH3Cl H C2H5 0 H H H COCH3Cl H C2H5 0 i-C3H7 H H
Cl H C2H5 0 i-C3H7 H H COCH3Cl H C2H5 0 i-C3H7 H H CO2CH3Cl H C2H5 0 n-C3H7 H H
Cl H C2H5 0 n-C3H7 H H COCH3Cl H C2H5 0 n-C3H7 H H CO2CH3Cl H C2H5 1 C2H5 H H
Cl H C2H5 1 C2H5 H H COCH3Cl H C2H5 1 C2H5 H H CO2C2H5Cl H C2H5 1 C2H5 H H CO2CH3Cl H C2H5 1 CH2OC2H5 H H C2H5Cl H C2H5 1 CH2OC2H5 H H CH2OCH3Cl H C2H5 1 CH2OC2H5 H H CH3Cl H C2H5 1 CH2OC2H5 H H n-C3H7
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 1 CH2OC2H5 H H n-C4H9Cl H C2H5 1 CH2OC2H5 H H t-C4H9Cl H C2H5 1 CH2OCH3 H H C2H5Cl H C2H5 1 CH2OCH3 H H CH2OCH3Cl H C2H5 1 CH2OCH3 H H CH3Cl H C2H5 1 CH2OCH3 H H n-C3H7Cl H C2H5 1 CH2OCH3 H H n-C4H9Cl H C2H5 1 CH2OCH3 H H t-C4H9Cl H C2H5 1 CH2SCH3 H H C2H5Cl H C2H5 1 CH2SCH3 H H CH2OCH3Cl H C2H5 1 CH2SCH3 H H CH3Cl H C2H5 1 CH2SCH3 H H n-C3H7Cl H C2H5 1 CH2SCH3 H H n-C4H9Cl H C2H5 1 CH2SCH3 H H t-C4H9Cl H C2H5 1 CH3 H H
Cl H C2H5 1 CH3 H H COCH3Cl H C2H5 1 CH3 H H CO2C2H5Cl H C2H5 1 CH3 H H CO2CH3Cl H C2H5 1 COC2H5 H H C2H5Cl H C2H5 1 COC2H5 H H CH2OCH3Cl H C2H5 1 COC2H5 H H CH3Cl H C2H5 1 COC2H5 H H n-C3H7Cl H C2H5 1 COC2H5 H H n-C4H9Cl H C2H5 1 COC2H5 H H t-C4H9Cl H C2H5 1 COC3H7-n H H C2H5Cl H C2H5 1 COC3H7-n H H CH2OCH3Cl H C2H5 1 COC3H7-n H H CH3Cl H C2H5 1 COC3H7-n H H n-C3H7Cl H C2H5 1 COC3H7-n H H n-C4H9Cl H C2H5 1 COC3H7-n H H t-C4H9Cl H C2H5 1 COCH3 H H C2H5Cl H C2H5 1 COCH3 H H CH2OCH3Cl H C2H5 1 COCH3 H H CH3Cl H C2H5 1 COCH3 H H n-C3H7Cl H C2H5 1 COCH3 H H n-C4H9Cl H C2H5 1 COCH3 H H t-C4H9Cl H C2H5 1 H H H (CH2)5BrCl H C2H5 1 H H H CH2CH2CO2HCl H C2H5 1 H H H CH2CH2SCH3Cl H C2H5 1 H H H CO2C2H5Cl H C2H5 1 H H H CO2CH3Cl H C2H5 1 H H H COCH3
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 1 H H H
Cl H C2H5 1 H H H
Cl H C2H5 1 H H H s-C4H9Cl H C2H5 1 i-C3H7 H H
Cl H C2H5 1 i-C3H7 H H COCH3Cl H C2H5 1 i-C3H7 H H CO2CH3Cl H C2H5 1 n-C3H7 H H
Cl H C2H5 1 n-C3H7 H H COCH3Cl H C2H5 1 n-C3H7 H H CO2CH3Cl H C2H5 2 C2H5 H H
Cl H C2H5 2 C2H5 H H COCH3Cl H C2H5 2 C2H5 H H CO2C2H5Cl H C2H5 2 C2H5 H H CO2CH3Cl H C2H5 2 CH2OC2H5 H H C2H5Cl H C2H5 2 CH2OC2H5 H H CH2OCH3Cl H C2H5 2 CH2OC2H5 H H CH3Cl H C2H5 2 CH2OC2H5 H H n-C3H7Cl H C2H5 2 CH2OC2H5 H H n-C4H9Cl H C2H5 2 CH2OC2H5 H H t-C4H9Cl H C2H5 2 CH2OCH3 H H C2H5Cl H C2H5 2 CH2OCH3 H H CH2OCH3Cl H C2H5 2 CH2OCH3 H H CH3Cl H C2H5 2 CH2OCH3 H H n-C3H7Cl H C2H5 2 CH2OCH3 H H n-C4H9Cl H C2H5 2 CH2OCH3 H H t-C4H9Cl H C2H5 2 CH2SCH3 H H C2H5Cl H C2H5 2 CH2SCH3 H H CH2OCH3Cl H C2H5 2 CH2SCH3 H H CH3Cl H C2H5 2 CH2SCH3 H H n-C3H7Cl H C2H5 2 CH2SCH3 H H n-C4H9Cl H C2H5 2 CH2SCH3 H H t-C4H9Cl H C2H5 2 CH3 H H
Cl H C2H5 2 CH3 H H COCH3Cl H C2H5 2 CH3 H H CO2C2H5Cl H C2H5 2 CH3 H H CO2CH3Cl H C2H5 2 COC2H5 H H C2H5Cl H C2H5 2 COC2H5 H H CH2OCH3Cl H C2H5 2 COC2H5 H H CH3Cl H C2H5 2 COC2H5 H H n-C3H7
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H C2H5 2 COC2H5 H H n-C4H9Cl H C2H5 2 COC2H5 H H t-C4H9Cl H C2H5 2 COC3H7-n H H C2H5Cl H C2H5 2 COC3H7-n H H CH2OCH3Cl H C2H5 2 COC3H7-n H H CH3Cl H C2H5 2 COC3H7-n H H n-C3H7Cl H C2H5 2 COC3H7-n H H n-C4H9Cl H C2H5 2 COC3H7-n H H t-C4H9Cl H C2H5 2 COCH3 H H C2H5Cl H C2H5 2 COCH3 H H CH2OCH3Cl H C2H5 2 COCH3 H H CH3Cl H C2H5 2 COCH3 H H n-C3H7Cl H C2H5 2 COCH3 H H n-C4H9Cl H C2H5 2 COCH3 H H t-C4H9Cl H C2H5 2 H H H (CH2)5BrCl H C2H5 2 H H H CH2CH2CO2HCl H C2H5 2 H H H CH2CH2SCH3Cl H C2H5 2 H H H CO2C2H5Cl H C2H5 2 H H H CO2CH3Cl H C2H5 2 H H H COCH3Cl H C2H5 2 H H H
Cl H C2H5 2 H H H
Cl H C2H5 2 H H H s-C4H9Cl H C2H5 2 i-C3H7 H H
Cl H C2H5 2 i-C3H7 H H COCH3Cl H C2H5 2 i-C3H7 H H CO2CH3Cl H C2H5 2 n-C3H7 H H
Cl H C2H5 2 n-C3H7 H H COCH3Cl H C2H5 2 n-C3H7 H H CO2CH3Cl H CH2CF3 0 C2H5 H H C2H5Cl H CH2CF3 0 C2H5 H H CH2OCH3Cl H CH2CF3 0 C2H5 H H CH3Cl H CH2CF3 0 C2H5 H H n-C3H7Cl H CH2CF3 0 CH3 H H C2H5Cl H CH2CF3 0 CH3 H H CH2OCH3Cl H CH2CF3 0 CH3 H H CH3Cl H CH2CF3 0 CH3 H H n-C3H7Cl H CH2CF3 1 C2H5 H H C2H5Cl H CH2CF3 1 C2H5 H H CH2OCH3
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH2CF3 1 C2H5 H H CH3Cl H CH2CF3 1 C2H5 H H n-C3H7Cl H CH2CF3 1 CH3 H H C2H5Cl H CH2CF3 1 CH3 H H CH2OCH3Cl H CH2CF3 1 CH3 H H CH3Cl H CH2CF3 1 CH3 H H n-C3H7Cl H CH2CF3 2 C2H5 H H C2H5Cl H CH2CF3 2 C2H5 H H CH2OCH3Cl H CH2CF3 2 C2H5 H H CH3Cl H CH2CF3 2 C2H5 H H n-C3H7Cl H CH2CF3 2 CH3 H H C2H5Cl H CH2CF3 2 CH3 H H CH2OCH3Cl H CH2CF3 2 CH3 H H CH3Cl H CH2CF3 2 CH3 H H n-C3H7Cl H CH3 0 C2H5 H H
Cl H CH3 0 C2H5 H H COCH3Cl H CH3 0 C2H5 H H CO2C2H5Cl H CH3 0 C2H5 H H CO2CH3Cl H CH3 0 CH2OC2H5 H H C2H5Cl H CH3 0 CH2OC2H5 H H CH2OCH3Cl H CH3 0 CH2OC2H5 H H n-C3H7Cl H CH3 0 CH2OC2H5 H H n-C4H9Cl H CH3 0 CH2OC2H5 H H t-C4H9Cl H CH3 0 CH2OCH3 H H C2H5Cl H CH3 0 CH2OCH3 H H CH2OCH3Cl H CH3 0 CH2OCH3 H H n-C3H7Cl H CH3 0 CH2OCH3 H H n-C4H9Cl H CH3 0 CH2OCH3 H H t-C4H9Cl H CH3 0 CH2SCH3 H H C2H5Cl H CH3 0 CH2SCH3 H H CH2OCH3Cl H CH3 0 CH2SCH3 H H n-C3H7Cl H CH3 0 CH2SCH3 H H n-C4H9Cl H CH3 0 CH2SCH3 H H t-C4H9Cl H CH3 0 CH3 H H
Cl H CH3 0 CH3 H H COCH3Cl H CH3 0 CH3 H H CO2C2H5Cl H CH3 0 CH3 H H CO2CH3Cl H CH3 0 COC2H5 H H C2H5Cl H CH3 0 COC2H5 H H CH2OCH3Cl H CH3 0 COC2H5 H H n-C3H7Cl H CH3 0 COC2H5 H H n-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 0 COC2H5 H H t-C4H9Cl H CH3 0 COC3H7-n H H C2H5Cl H CH3 0 COC3H7-n H H CH2OCH3Cl H CH3 0 COC3H7-n H H CH3Cl H CH3 0 COC3H7-n H H n-C3H7Cl H CH3 0 COC3H7-n H H n-C4H9Cl H CH3 0 COC3H7-n H H t-C4H9Cl H CH3 0 COC6H5 H H CH3Cl H CH3 0 COCH3 H H C2H5Cl H CH3 0 COCH3 H H CH2OCH3Cl H CH3 0 COCH3 H H n-C3H7Cl H CH3 0 COCH3 H H n-C4H9Cl H CH3 0 COCH3 H H t-C4H9Cl H CH3 0 H H H (CH2)5BrCl H CH3 0 H H H CH2CH2CO2HCl H CH3 0 H H H CH2CH2SCH3Cl H CH3 0 H H H CH2CO2CH3Cl H CH3 0 H H H CO2C2H5Cl H CH3 0 H H H CO2CH3Cl H CH3 0 H H H COCH3Cl H CH3 0 i-C3H7 H H
Cl H CH3 0 i-C3H7 H H COCH3Cl H CH3 0 i-C3H7 H H CO2CH3Cl H CH3 0 n-C3H7 H H
Cl H CH3 0 n-C3H7 H H COCH3Cl H CH3 0 n-C3H7 H H CO2CH3Cl H CH3 1 C2H5 H H
Cl H CH3 1 C2H5 H H COCH3Cl H CH3 1 C2H5 H H CO2C2H5Cl H CH3 1 C2H5 H H CO2CH3Cl H CH3 1 CH2OC2H5 H H C2H5Cl H CH3 1 CH2OC2H5 H H CH2OCH3Cl H CH3 1 CH2OC2H5 H H CH3Cl H CH3 1 CH2OC2H5 H H n-C3H7Cl H CH3 1 CH2OC2H5 H H n-C4H9Cl H CH3 1 CH2OC2H5 H H t-C4H9Cl H CH3 1 CH2OCH3 H H C2H5Cl H CH3 1 CH2OCH3 H H CH2OCH3Cl H CH3 1 CH2OCH3 H H CH3Cl H CH3 1 CH2OCH3 H H n-C3H7
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 1 CH2OCH3 H H n-C4H9Cl H CH3 1 CH2OCH3 H H t-C4H9Cl H CH3 1 CH2SCH3 H H C2H5Cl H CH3 1 CH2SCH3 H H CH2OCH3Cl H CH3 1 CH2SCH3 H H CH3Cl H CH3 1 CH2SCH3 H H n-C3H7Cl H CH3 1 CH2SCH3 H H n-C4H9Cl H CH3 1 CH2SCH3 H H t-C4H9Cl H CH3 1 CH3 H H
Cl H CH3 1 CH3 H H COCH3Cl H CH3 1 CH3 H H CO2C2H5Cl H CH3 1 CH3 H H CO2CH3Cl H CH3 1 COC2H5 H H C2H5Cl H CH3 1 COC2H5 H H CH2OCH3Cl H CH3 1 COC2H5 H H CH3Cl H CH3 1 COC2H5 H H n-C3H7Cl H CH3 1 COC2H5 H H n-C4H9Cl H CH3 1 COC2H5 H H t-C4H9Cl H CH3 1 COC3H7-n H H C2H5Cl H CH3 1 COC3H7-n H H CH2OCH3Cl H CH3 1 COC3H7-n H H CH3Cl H CH3 1 COC3H7-n H H n-C3H7Cl H CH3 1 COC3H7-n H H n-C4H9Cl H CH3 1 COC3H7-n H H t-C4H9Cl H CH3 1 COCH3 H H C2H5Cl H CH3 1 COCH3 H H CH2OCH3Cl H CH3 1 COCH3 H H CH3Cl H CH3 1 COCH3 H H n-C3H7Cl H CH3 1 COCH3 H H n-C4H9Cl H CH3 1 COCH3 H H t-C4H9Cl H CH3 1 H H H (CH2)5BrCl H CH3 1 H H H CH2CH2COxHCl H CH3 1 H H H CH2CH2SCH3Cl H CH3 1 H H H CH2CO2CH3Cl H CH3 1 H H H CO2C2H5Cl H CH3 1 H H H CO2CH3Cl H CH3 1 H H H COCH3Cl H CH3 1 H H H
Cl H CH3 1 H H H
Cl H CH3 1 H H H s-C4H9
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 1 i-C3H7 H H
Cl H CH3 1 i-C3H7 H H COCH3Cl H CH3 1 i-C3H7 H H CO2CH3Cl H CH3 1 n-C3H7 H H
Cl H CH3 1 n-C3H7 H H COCH3Cl H CH3 1 n-C3H7 H H CO2CH3Cl H CH3 2 C2H5 H H
Cl H CH3 2 C2H5 H H COCH3Cl H CH3 2 C2H5 H H CO2C2H5Cl H CH3 2 C2H5 H H CO2CH3Cl H CH3 2 CH2OC2H5 H H C2H5Cl H CH3 2 CH2OC2H5 H H CH2OCH3Cl H CH3 2 CH2OC2H5 H H CH3Cl H CH3 2 CH2OC2H5 H H n-C3H7Cl H CH3 2 CH2OC2H5 H H n-C4H9Cl H CH3 2 CH2OC2H5 H H t-C4H9Cl H CH3 2 CH2OCH3 H H C2H5Cl H CH3 2 CH2OCH3 H H CH2OCH3Cl H CH3 2 CH2OCH3 H H CH3Cl H CH3 2 CH2OCH3 H H n-C3H7Cl H CH3 2 CH2OCH3 H H n-C4H9Cl H CH3 2 CH2OCH3 H H t-C4H9Cl H CH3 2 CH2SCH3 H H C2H5Cl H CH3 2 CH2SCH3 H H CH2OCH3Cl H CH3 2 CH2SCH3 H H CH3Cl H CH3 2 CH2SCH3 H H n-C3H7Cl H CH3 2 CH2SCH3 H H n-C4H9Cl H CH3 2 CH2SCH3 H H t-C4H9Cl H CH3 2 CH3 H H
Cl H CH3 2 CH3 H H COCH3Cl H CH3 2 CH3 H H CO2C2H5Cl H CH3 2 CH3 H H CO2CH3Cl H CH3 2 COC2H5 H H C2H5Cl H CH3 2 COC2H5 H H CH2OCH3Cl H CH3 2 COC2H5 H H CH3Cl H CH3 2 COC2H5 H H n-C3H7Cl H CH3 2 COC2H5 H H n-C4H9Cl H CH3 2 COC2H5 H H t-C4H9Cl H CH3 2 COC3H7-n H H C2H5
表2(续)R1 R2 R3 n R5 R6 R7 R8Cl H CH3 2 COC3H7-n H H CH2OCH3Cl H CH3 2 COC3H7-n H H CH3Cl H CH3 2 COC3H7-n H H n-C3H7Cl H CH3 2 COC3H7-n H H n-C4H9Cl H CH3 2 COC3H7-n H H t-C4H9Cl H CH3 2 COCH3 H H C2H5Cl H CH3 2 COCH3 H H CH2OCH3Cl H CH3 2 COCH3 H H CH3Cl H CH3 2 COCH3 H H n-C3H7Cl H CH3 2 COCH3 H H n-C4H9Cl H CH3 2 COCH3 H H 1-C4H9Cl H CH3 2 H H H (CH2)5BrCl H CH3 2 H H H CH2CH2CO2HCl H CH3 2 H H H CH2CH2SCH3Cl H CH3 2 H H H CH2CO2CH3Cl H CH3 2 H H H CO2C2H5Cl H CH3 2 H H H CO2CH3Cl H CH3 2 H H H COCH3Cl H CH3 2 H H H
Cl H CH3 2 H H H
Cl H CH3 2 H H H s-C4H9Cl H CH3 2 i-C3H7 H H
Cl H CH3 2 i-C3H7 H H COCH3Cl H CH3 2 i-C3H7 H H CO2CH3Cl H CH3 2 n-C3H7 H H
Cl H CH3 2 n-C3H7 H H COCH3Cl H CH3 2 n-C3H7 H H CO2CH3
表3
R1 R2 R3 n R4 R5 R6 R7Br H C2H5 0 H H H HBr H C2H5 0 t-C4H9 H H HBr H C2H5 2 H H H HBr H C2H5 1 H H H HBr H CH3 0 H H H HBr H CH3 0 t-C4H9 H H HBr H CH3 2 H H H HBr H CH3 2 CH3 CH3 H HBr H CH3 2 CH3 H H HBr H CH3 2 C6H5 H H HBr H CH3 2
H H HBr H CH3 1 H H H HCl H C2H5 0 H H H HCl H C2H5 0 t-C4H9 H H HCl H C2H5 2 H H H HCl H C2H5 2 CH3 CH3 H HCl H C2H5 2 CH3 H H HCl H C2H5 2 C6H5 H H HCl H C2H5 2
H H HCl H C2H5 2
H H HCl H C2H5 1 H H H HCl H CH3 0 H H H HCl H CH3 0 t-C4H9 H H HCl H CH3 2 H H H HCl H CH3 2 CH3 H H HCl H CH3 2 i-C3H7 H H HCl H CH3 2 CH2CH=CH2 H H HCl H CH3 2 CH3 CH3 H HCl H CH3 2 n-C4H9 H H H
表3(续)R1 R2 R3 n R4 R5 R6 R7Cl H CH3 2 CH2C6H5 H H HCl H CH3 2 CH3 C6H5 H HCl H CH3 2 C6H5 H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 2
H H HCl H CH3 1 H H H HCl H CHF2 0 H H H HCl H CHF2 1 H H H HCl H CF3 0 H H H HCl H CH2CF3 0 H H H HCl H CH2CH2F 0 H H H HCl H CH2CHF2 0 H H H H
表4
R1 R2 R3 n R5 R6 R7 Z R10 R11Br H CH3 0 H H H O H C6H5Br H CH3 0 H H H O H HBr H CH3 0 H H H S H HBr H CH3 1 H H H O H HCl H CH2CF3 0 H H H O H HCl H CH2CF3 0 H H H S H HCl H CH2CH2F 0 H H H O H HCl H CH2CH2F 0 H H H S H HCl H CH2CHF2 0 H H H O H HCl H CH2CHF2 0 H H H S H HCl H CH3 0 H H H S CH3 CH3Cl H CH3 0 H H H O H C2H5Cl H CH3 0 H H H O H
Cl H CH3 0 H H H O H
Cl H CH3 0 H H H O H C6H5Cl H CH3 0 H H H S H C6H5Cl H CH3 0 H H H O H CH2CH2ClCl H CH3 0 H H H O H CH3Cl H CH3 0 H H H S H CH3Cl H CH3 0 H H H O H HCl H CH3 0 H H H S H HCl H CH3 2 H H H O H C2H5Cl H CH3 2 H H H S H H
表4(续)R1 R2 R3 n R5 R6 R7 Z R10 R11Cl H CH3 1 H H H S H HCl H CH3 0 H H H O H
Cl H CH3 0 H H H O H
Cl H CH3 0 H H H S H
在方法(c)中,如果例如用4-氯-4’-甲硫基甲基二苯酮腙和氯甲酸异丁酯作为起始原料,该反应以反应式解释如下:
在方法(e)中,如果用高碘酸钠氧化4-氯4’-甲硫基甲基二苯酮乙氧羰基腙,该反应通过反应式解释如下:
在方法(a)中,式(II)化合物指的是基于上述R1、R2、R3、R6、R7和n的定义的那些化合物,优选基于上述优选定义的那些化合物。
式(II)的原料化合物是新化合物,并可通过下述方法制得:
(g)当n是0时,
在惰性溶剂存在下,和适当的话在酸结合剂存在下,使式(XI)化合物
式中R1、R2、R6、R7和hal的定义同前,与式(XII)化合物或其盐反应,
R3-SH (XII)
式中R3的定义同前;或者
(h)当n为0时,
在惰性溶剂存在下,和适当的话在酸结合剂存在下,使式(XIII)化合物或其盐
式中R1、R2、R6和R7的定义同前,与式(XIV)化合物反应,
R15-R3 (XIV)
式中R3的定义同前,和R15是氯、溴或碘;或者
(j)当n是0且R1是氟或氯时,
式中R6的定义同前,R16是氟或氯,和R17是锂、溴化镁或碘化镁;
或者
(k)当n是0时,
式中R1和R6的定义同前;或者
(m)当n是0,R2是氢且R3是全氟烷基,则R3由R18代替时,
式中R1、R6和R7的定义同前,与式(XX)化合物反应,
R18-I (XX)
式中R18是C1-4全氟烷基;或者
(n)当n是0且R2是C1-4烷基,则R2由R19代替时,
式中R1、R3、R6和R7的定义同前,与式(XXII)化合物反应,
hal-R19 (XXII)
式中hal的定义同前,且R19是C1-4烷基;或者
(p)当n是1时,
式中R1、R2、R3、R6和R7的定义同前;或者
(q)当D是2时
式中R1、R2、R3、R6、R7和q的定义同前。
式(II)化合物的实例示于表5中。
表5
R1 R6 R7 A R1 R6 R7 ABr H H CH(CH3)SCH3 Cl H H CH2S(CH2)3FBr H H CH(CH3)SO2CH3 Cl H H CH2SC2H5Br H H CH(CH3)SOCH3 Cl H H CH2SC3H7-iBr H H CH2SC2H5 Cl H H CH2SC3H7-nBr H H CH2SC3H7-n Cl H H CH2SC4H9-nBr H H CH2SCF3 Cl H H CH2SC4H9-sBr H H CH2SCH2CF3 Cl H H CH2SCF2CF2CF3Br H H CH2SCH2CH=CH2 Cl H H CH2SCF2CF3Br H H CH2SCH2CH2F Cl H H CH2SCF2CHF2Br H H CH2SCH2CHF2 Cl H H CH2SCF3Br H H CH2SCH2F Cl H H CH2SCH2C≡CHBr H H CH2SCH3 Cl H H CH2SCH2CF2CF2HBr H H CH2SCHF2 Cl H H CH2SCH2CF2CF3Br H H CH2SO2C2H5 Cl H H CH2SCH2CF3Br H H CH2SO2C3H7-n Cl H H CH2SCH=CH2Br H H CH2SO2CH2CF3 Cl H H CH2SCH2CH=CH2Br H H CH2SO2CH2CH=CH2 Cl H H CH2SCH2CH2CH2ClBr H H CH2SO2CH2CH2F Cl H H CH2SCH2CH2ClBr H H CH2SO2CH2CHF2 Cl H H CH2SCH2CH2FBr H H CH2SO2CH3 Cl H H CH2SCH2CHF2Br H H CH2SOC2H5 Cl H H CH2SCH2CNBr H H CH2SOC3H7-n Cl H H CH2SCH2FBr H H CH2SOCH2CF3 Cl H H CH2SCH2ClBr H H CH2SOCH2CH=CH2 Cl H H CH2SCH3Br H H CH2SOCH2CH2F Cl H 2-Cl CH2SCH3Br H H CH2SOCH2CHF2 Cl H 3-Cl CH2SCH3Br H H CH2SOCH2F Cl H 2-F CH2SCH3Br H H CH2SOCH3 Cl H 3-F CH2SCH3Br H H CH2SOCHF2 Cl H 2-Br CH2SCH3Cl H H CH(C2H5)SCH3 Cl H 3-Br CH2SCH3Cl H H CH(C2H5)SO2CH3 Cl H 3-CH3 CH2SCH3Cl H H CH(C2H5)SOCH3 Cl H 2-CH3 CH2SCH3Cl H H CH(CH3)SCH3 Cl H H CH2SCHF2Cl H H CH(CH3)SO2CH3 Cl H H CH2SO2C2H5Cl H H CH(CH3)SOCH3 Cl H H CH2SO2C3H7-nCl H H CH(n-C3H7)SCH3 Cl H H CH2SO2CH2C≡CH
表5(续)R1 R6 R7 A R1 R6 R7 ACl H H CH2SO2CH2CF3 Cl 3-F H CH2SCH3Cl H H CH2SO2CH2CH=CH2 Cl 2-Cl H CH2SO2C2H5Cl H H CH2SO2CH2CH2CH2F Cl 2-F H CH2SO2C2H5Cl H H CH2SO2CH2CH2CH2Cl Cl 3-F H CH2SO2C2H5Cl H H CH2SO2CH2CH2Cl Cl 2-Cl H CH2SO2CH3Cl H H CH2SO2CH2CH2F Cl 2-F H CH2SO2CH3Cl H H CH2SO2CH2CHF2 Cl 3-F H CH2SO2CH3Cl H H CH2SO2CH3 Cl 2-Cl H CH2SOC2H5Cl H 2-Cl CH2SO2CH3 Cl 2-F H CH2SOC2H5Cl H 3-Cl CH2SO2CH3 Cl 3-F H CH2SOC2H5Cl H 2-F CH2SO2CH3 Cl 2-Cl H CH2SOCH3Cl H 3-F CH2SO2CH3 Cl 2-F H CH2SOCH3Cl H 2-Br CH2SO2CH3 Cl 3-F H CH2SOCH3Cl H 3-Br CH2SO2CH3 Cl 3-Cl H CH2SC2H5Cl H 3-CH3 CH2SO2CH3 Cl 3-Cl H CH2SCH3Cl H 2-CH3 CH2SO2CH3 Cl 3-Cl H CH2SO2C2H5Cl H H CH2SOC2H5 Cl 3-Cl H CH2SO2CH3Cl H H CH2SOC3H7-n Cl 3-Cl H CH2SOC2H5Cl H H CH2SOCH2C≡CH Cl 3-Cl H CH2SOCH3Cl H H CH2SOCH2CF3 F H H CH2SC2H5Cl H H CH2SOCH2CH=CH2 F H H CH2SCH3Cl H H CH2SOCH2CH2CH2Cl F H H CH2SO2C2H5Cl H H CH2SOCH2CH2Cl F H H CH2SO2CH3Cl H H CH2SOCH2CH2F F H H CH2SOC2H5Cl H H CH2SOCH2CHF2 F H H CH2SOCH3Cl H H CH2SOCH2F F 3-F H CH2SC2H5Cl H H CH2SOCH3 F 3-F H CH2SCH3Cl H 2-Cl CH2SOCH3 F 3-F H CH2SO2C2H5Cl H 3-Cl CH2SOCH3 F 3-F H CH2SO2CH3Cl H 2-F CH2SOCH3 F 3-F H CH2SOC2H5Cl H 3-F CH2SOCH3 F 3-F H CH2SOCH3Cl H 2-Br CH2SOCH3 I H H CH2SC2H5Cl H 3-Br CH2SOCH3 I H H CH2SCF3Cl H 3-CH3 CH2SOCH3 I H H CH2SCH2CF3Cl H 2-CH3 CH2SOCH3 I H H CH2SCH2CH2FCl H H CH2SOCHF2 I H H CH2SCH2CHF2Cl 2-Cl H CH2SC2H5 I H H CH2SCH3Cl 2-F H CH2SC2H5 I H H CH2SCHF2Cl 3-F H CH2SC2H5 I H H CH2SO2C2H5Cl 2-Cl H CH2SCH3 I H H CH2SO2CH3Cl 2-F H CH2SCH3 I H H CH2SOC2H5
表5(续)R1 R6 R7 AI H H CH2SOCH3Cl H H CH2SOCH3Cl H H CH2SCNCl H H CH2SCSOCH3Cl H H CH2CSOC2H5Cl H H CH2SCH2Si(CH3)3Cl H H CH2SOCH2Si(CH3)3Cl H H CH2SO2CH2Si(CH3)3Br H H CH2SCH2Si(CH3)3Br H H CH2SOCH2Si(CH3)3Br H H CH2SO2CH2Si(CH3)3
在方法(g)中,式(XI)的原料是部分已知的,例如4-氯-4’-氯甲基二苯酮及其制备方法描述于日本专利特开昭46-10164中;或者式(XI)的原料可按常规方法,例如用N-溴代琥珀酰亚胺或N-氯代琥珀酰亚胺作为卤化剂,卤化式(XXV)的二苯酮来制备,
式中R1、R2、R6和R7的定义同前。
式(XXV)的化合物可通过Fridel-Crafts反应制得,其中取代的苯甲酰卤和烷基取代的苯用作起始原料,且使用氯化铝作为催化剂。
式(XI)的化合物可举例如下:
4-氯-4’-氯甲基二苯酮,
4-氯甲基-4’-氟二苯酮,
4-溴-4’-氯甲基二苯酮,
4-溴甲基-4’-氯二苯酮,
4-溴甲基-4’-氟二苯酮,
4-溴-4’-溴甲基二苯酮,
4-(1-溴乙基)-4’-氯-二苯酮,
4-(1-溴丙基)-4’-氯二苯酮,等等。
在上述方法(g)中,式(XII)化合物是有机化学领域已知的,例如可提及的有:
甲硫醇及其盐,
乙硫醇及其盐,等等。
在上述方法(h)中,式(XIII)的化合物是新的,这些化合物可通过下法合成:例如,使上述的式(XI)的二苯酮与硫脲反应。该反应本身是有机化学领域公知的,并可按类似于“Jikken Kagaku Koza(Experimental ChemistryCourse)”fourth edition,edited by Japanese Chemistry Society,Vol.25,page 336,1992,published by Maruzen中描述的方法进行。
式(XIII)的化合物实例示于下表6中:
表6
R1 R6 R7 ABr H H CH2SC(=NH)NH2·HBrCl H H CH(C2H5)SC(=NH)NH2·HBrCl H H CH(CH3)SC(=NH)NH2·HBrCl H H CH(n-C3H7)SC(=NH)NH2·HBrCl H H CH2SC(=NH)NH2·HBrCl H 2-CH3 CH2SC(=NH)NH2·HBrCl H 3-CH3 CH2SC(=NH)NH2·HBrCl H 2-F CH2SC(=NH)NH2·HBrCl H 3-F CH2SC(=NH)NH2·HBrCl H 2-Cl CH2SC(=NH)NH2·HBrCl H 3-Cl CH2SC(=NH)NH2·HBrCl H 2-Br CH2SC(=NH)NH2·HBrCl H 3-Br CH2SC(=NH)NH2·HBrCl 2-Cl H CH2SC(=NH)NH2·HBrCl 2-F H CH2SC(=NH)NH2·HBrCl 3-F H CH2SC(=NH)NH2·HBrCl 3-Cl H CH2SC(=NH)NH2·HBrF H H CH2SC(=NH)NH2·HBrF 3-F H CH2SC(=NH)NH2·HBrI H H CH2SC(=NH)NH2·HBr
在方法(h)中,式(XIV)的化合物是有机化学领域已知的,例如可提及的有:碘甲烷、碘乙烷、溴甲烷、溴乙烷、溴二氟甲烷、碘三氟甲烷、1-溴-2-氟乙烷、1-溴-2-氯乙烷、2,2,2-三氟-1-碘乙烷、1-溴-2,2-二溴乙烷等。
在方法(j)中,式(XV)的化合物可按下法制得:在与方法(g)相同的反应条件下,在酸结合剂存在下且适当的话在惰性溶剂存在下,将式(XXVI)的化合物与式(XII)化合物反应,
式(XXVI)的化合物是已知的,其实例包括:4-氰基苄基溴、4-氰基苄基氯等。
在方法(j)中,式(XV)化合物是已知的,其实例是:4-甲硫基苄腈等。
在方法(j)中,式(XVI)化合物通过下法制得:在惰性溶剂存在下,且适当的话在催化剂存在下,用烷基锂或镁使式(XXVII)的化合物金属化,
式中R6和R16的定义同前,R20是溴或碘。
可提及的式(XXVII)的化合物实例如下:
4-氟溴苯、4-氟碘苯、4-氯碘苯、4-氯溴苯、2-氟-4-氯溴苯、3-氟-4-氯溴苯等。
在方法(k)中,式(XVII)的化合物通过下法制得:在惰性溶剂存在下,且适当的话在催化剂存在下,用烷基锂或镁使式(XXVIII)的化合物金属化,
式中R2、R3、R7和R20的定义同前。
式(XXVII)的化合物是已知的,并包括下述化合物:例如4-甲硫甲基溴苯、4-甲硫甲基碘苯、4-乙硫甲基溴苯、4-乙硫甲基碘苯等。
在方法(m)中,式(XIX)化合物是有机化学领域已知的化合物,且包括如下:硫氰酸4-(4-氯苯甲酰基)苄基酯等。
在方法(m)中,式(XX)化合物是有机化学领域已知的,并包括如下:碘三氟甲烷、碘五氟乙烷等。
方法(m)中的反应可按类似于Journal of Fluorine Chemistry,Vol.43,27-24(1989)中描述的方法进行。
在方法(n)中,式(XXI)的化合物通过上述的方法(g)至(m)来合成。且包括下述实例化合物:
4-氟-4’-甲硫甲基二苯酮,
4-氯-4’-甲硫甲基二苯酮,
4-溴-4’-甲硫甲基二苯酮,
4-碘-4’-甲硫甲基二苯酮,
4-氟-4’-乙硫甲基二苯酮,
4-氯-4’-乙硫甲基二苯酮,
4-溴-4’-乙硫甲基二苯酮,等等。
在方法(n)中,式(XXII)的化合物是有机化学领域已知的,其实施包括:碘甲烷、碘乙烷、溴甲烷、溴乙烷等。
方法(n)本身是有机化学领域已知的,例如,可按类似于“Jikken kagakuKoza(Experimental Chemistry Course)”fourth edition,edited by JapaneseChemical Society,Vol.25,page 329,1992,published by Maruzen中描述的方法进行反应。
在方法(n)中,通过上述的方法(g)至(n)合成式(XXIII)化合物。作为其实例,除了作为上述式(XXI)化合物列举的那些化合物外,还包括下述实例化合物:
4-溴-4’-(1-甲硫乙基)二苯酮,
4-氯-4’-(1-甲硫乙基)二苯酮,
4-溴-4’-(1-甲硫丙基)二苯酮,
4-溴-4’-(1-甲硫丁基)二苯酮,等等。
作为上述方法(p)中用的氧化剂,可提及的实例有:过氧化氢水溶液、过乙酸、间氯过苯甲酸、OXONETM、高碘酸钠、叔丁基过氧化氢和N-溴代琥珀酰亚胺。
上述制备方法(p)和(q)中的氧化反应,可按例如类似于“Jikken KagakuKoza(Experimental Chemistry Course)”fourth edition,edited by JapaneseChemical Society,Vol.25,page 350或365,1992,published by Maruzen中描述的方法进行反应。
在上述的方法(q)中,按上述的制备方法(g)至(p)合成式(XXIV)的化合物。作为其实例,除了上述作为式(XXI)和(XXIII)的化合物举例的那些化合物外,还可提及下列化合物:
4-氟-4’-甲亚磺酰基甲基二苯酮,
4-氯-4’-甲亚磺酰基甲基二苯酮,
4-氯-4’-二氟甲亚磺酰基甲基二苯酮,
4-溴-4’-甲亚磺酰基甲基二苯酮,
4-碘-4’-甲亚磺酰基甲基二苯酮,
4-乙亚磺酰基甲基-4’-氟二苯酮,
4-氯-4’-乙亚磺酰基甲基二苯酮,
4-溴-4’-乙亚磺酰基甲基二苯酮,
4-溴-4’-(1-甲亚磺酰乙基)二苯酮,
4-氯-4’-(1-甲亚磺酰乙基)二苯酮,
4-氯-4’-(1-甲亚磺酰丙基)二苯酮,
4-氯-4’-(1-甲亚磺酰丁基)二苯酮,等等。
作为可用于上述制备方法(q)中的氧化剂,除了上述的有关制备方法(p)中描述的那些氧化剂外还可提及的实例有:高锰酸钾、过硼酸钠。
在方法(a)中,式(III)的起始化合物是指基于上述R4定义的化合物,优选基于上述优选定义的化合物。
在方法(a)中,式(III)化合物是有机化学领域已知的,其实例包括:
水合肼、肼基甲酸甲酯、肼基甲酸乙酯、肼基甲酸正丙酯、肼基甲酸异丙酯、肼基甲酸正丁酯、肼基甲酸异丁酯、叔丁基肼、乙酰肼、苯甲酰肼、氨基脲、氨基硫脲、甲酰肼等。
在方法(b)和(c)中,式(IV)的原料化合物指的是基于上述R1、R2、R3、R6、R7和n定义的那些化合物,优选基于上述优选定义的那些化合物。
通过上述方法(a)、(d)、(e)和(f)合成式(IV)化合物,式(IV)化合物的具体实例包括下述化合物:
4-氟-4’-甲硫基甲基二苯酮腙,
4-氯-4’-甲硫基甲基二苯酮腙,
4-氯-4’-二氟甲硫基甲基二苯酮腙,
4-氯-4’-三氟甲硫基甲基二苯酮腙,
4-溴-4’-甲硫基甲基二苯酮腙,
4-乙硫基甲基-4’-氟二苯酮腙,
4-氯-4’-甲亚磺酰甲基二苯酮腙,
4-乙亚磺酰甲基-4’-溴二苯酮腙,
4-溴-4’-甲磺酰甲基二苯酮腙,
4-氯-4’-甲磺酰甲基二苯酮腙,等等。
在方法(b)中,作为起始原料的式(V)化合物是有机化学领域已知的,可提及的其实例如下:异氰酸4-三氟甲氧基苯基酯、异氰酸苯基酯等。
在方法(c)中,作为原料的式(VI)化合物是有机化学领域已知的,可提及的其实例如下:氯甲酸甲酯、氯甲酸乙酯、氯甲酸丙酯、氯甲酸异丙酯、氯甲酸丁酯、氯甲酸异丁酯、氯甲酸叔丁酯、溴甲酸甲酯、溴甲酸乙酯、溴甲酸丙酯、溴甲酸异丙酯、溴甲酸丁酯、溴甲酸异丁酯、溴甲酸叔丁酯、溴甲酸烯丙酯、乙酰氯、乙酰溴、丙酰氯、丁酰氯、异丁酰氯、戊酰氯、异戊酰氯、新戊酰氯等。
在方法(d)中,通过上述方法(a)、(b)、(c)和(f)合成式(VII)的化合物,其实例包括下列化合物:
4-氟-4’-甲硫基甲基二苯酮腙,
4-溴-4’-甲硫基甲基二苯酮腙,
4-碘-4’-甲硫基甲基二苯酮腙,
4-氯-4’-乙硫基甲基二苯酮腙,
4-溴-4’-甲硫基甲基二苯酮乙氧羰基腙,
4-氯-4’-甲硫基甲基二苯酮乙氧羰基腙,
4-氯-4’-乙硫基甲基二苯酮乙氧羰基腙,
4-氯-4’-(1-甲硫基乙基)二苯酮乙氧羰基腙等。
在方法(d)中,作为原料的式(VIII)化合物是有机化学领域已知的化合物,可提及的实例如下:
碘甲烷、碘乙烷、碘丙烷、氯甲基甲基醚、氯甲基乙基醚、氯甲基甲基硫醚、乙酰氯、苯甲酰氯、肉桂酰氯、氯甲酸甲酯、氯代碳酸甲酯、氯甲酸乙酯、氯甲酸丙酯、氯甲酸异丙酯、氯甲酸丁酯、氯甲酸异丁酯、氯甲酸叔丁酯、溴甲酸甲酯、溴甲酸乙酯、溴甲酸丙酯、溴甲酸异丙酯、溴甲酸丁酯、溴甲酸异丁酯、溴甲酸叔丁酯、溴甲酸烯丙酯等。
在方法(e)中,通过方法(a)至(d)可制得式(IX)化合物,除了作为式(IV)和(VII)化合物举例的那些化合物外,其实例还包括下述化合物。
作为用于上述方法(e)和(f)中的氧化剂,可提及有关方法(n)中描述的那些氧化剂。
在方法(f)中,式(X)的化合物是可通过上述方法(a)至(e)合成的本发明化合物。作为其实例,除了作为上述式(IV)和(VII)化合物举例的那些化合物外,还可提及下列化合物:
4-氟-4’-甲亚磺酰基甲基二苯酮腙,
4-溴-4’-甲亚磺酰基甲基二苯酮腙,
4-碘-4’-甲亚磺酰基甲基二苯酮腙,
4-氯-4’-乙亚磺酰基甲基二苯酮腙,
4-氯-4’-甲亚磺酰基甲基二苯酮乙氧羰基腙,和
4-溴-4’-乙亚磺酰基甲基二苯酮乙氧羰基腙。
如上所述,用作制备式(I)化合物的起始原料或中间体的式(II)、(XIII)、(XIX)、(XXI)、(XXIII)和(XXIV)化合物是新的,这些化合物可以由下式(XXIX)表示:
式中
R1为卤素,
R2为氢或C1-4烷基,
R6为氢或卤素,
R7为氢、卤素或C1-2烷基,
n为0、1或2,
X为氰基、任选地被取代的C1-4烷基、C2-4链烯基、C3-4炔基、
C1-4烷基-羰基、C1-4烷氧基-硫代羰基或甲脒基及它们的盐,
条件是,当X为氰基、C1-4烷基-羰基、C1-4烷氧基-硫代羰
基或甲脒基及它们的盐时,n为0。
上述生产方法(a)的反应可以在适当的稀释剂中进行。作为这样的稀释剂,可提及的是任选的惰性有机溶剂如脂族、脂环族或芳香烃类(它们可任选地被氯代)诸如戊烷、己烷、环己烷、石油醚、石油英、苯、甲苯、二甲苯、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、氯苯和二氯苯;醚类诸如乙醚、甲乙醚、异丙醚、丁醚、二噁烷、二甲氧基乙烷(DME)、四氢呋喃(THF)和二甘醇二甲醚(DGM);腈类诸如乙腈、丙腈和丙烯腈;醇类(条件是R3不是单卤代甲基)诸如甲醇、乙醇、异丙醇、丁醇和乙二醇;酯类诸如乙酸乙酯和乙酸戊酯;酰胺类诸如二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑烷酮和六甲基磷酸三酰胺(HMPA);以及砜类和亚砜类诸如二甲基亚砜(DMSO)和环丁砜。
上面生产方法(a)中的反应可以在酸催化剂存在下进行。可提及的可用的酸催化剂的例子有:无机酸诸如盐酸、硫酸、磷酸、氢溴酸,有机酸诸如甲酸、乙酸、三氟乙酸和丙酸,甲磺酸、苯磺酸和对甲苯磺酸,以及有机胺盐酸盐诸如吡啶盐酸盐和三乙胺盐酸盐等。
生产方法(a)的反应可以在很宽的温度范围内进行。但一般可使用约-20~约200℃的反应温度,优选约20~约150℃。此外,反应优选应该在常压下进行,但也可任选地在升高或降低的压力下进行。
为了进行生产方法(a),例如,可以在稀释剂诸如乙醇中在酸催化剂诸如乙酸存在下使1摩尔式(II)化合物与1-10摩尔式(III)化合物反应,由此得到式(I)的目的化合物。
在进行上述方法(b)时,可以用任何惰性溶剂作为合适的稀释剂。
这样稀释剂的实例有脂族、环脂族或芳香族的、任选被氯代的烃类诸如戊烷、己烷、环己烷、石油醚、石油英、苯、甲苯、二甲苯、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、氯苯、二氯苯等;醚类诸如乙醚、甲乙醚、异丙醚、丁醚、二噁烷、二甲氧基乙烷(DME)、四氢呋喃(THF)、二亚甲基二醇二甲醚等;酮类诸如丙酮、甲乙酮(MEK)、甲基异丙基酮、甲基异丁基酮(MIBK)等;腈类诸如乙腈、丙腈等;酯类诸如乙酸乙酯、乙酸戊酯等;酰胺类诸如二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑烷酮、六甲基磷酸三酰胺(HMPA)等;以及砜类和亚砜类诸如二甲基亚砜(DMSO)、环丁砜等;以及碱诸如吡啶。
在上述方法(b)中,反应温度可以在很宽范围内变化。通常,反应在大约-120℃~大约200℃的温度下进行,优选20℃~大约100℃的温度。
此外,反应在常压下进行,但也可以使用较高的或较低的压力。
当进行本发明的上述方法(b)时,例如在稀释剂诸如乙腈中就每摩尔式(IV)化合物使用大约1-3摩尔式(V)化合物,以获得所希望的化合物。
上述生产方法(c)的反应可以在适当的稀释剂例如任选的惰性有机溶剂中进行。这种有机溶剂的实例有:脂族、环脂族或芳香烃类(它们可任选地被氯代)诸如戊烷、己烷、环己烷、石油醚、石油英、苯、甲苯、二甲苯、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、氯苯和二氯苯;醚类诸如乙醚、甲乙醚、异丙醚、丁醚、二噁烷、二甲氧基乙烷(DME)、四氢呋喃(THF)和二甘醇二甲醚(DGM);酮类诸如丙酮、甲乙酮(MEK)、甲基异丙基酮和甲基异丁基酮(MIBK);腈类诸如乙腈、丙腈和丙烯腈;酯类诸如乙酸乙酯和乙酸戊酯;酰胺类诸如二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑烷酮和六甲基磷酸三酰胺(HMPA);以及砜类和亚砜类诸如二甲基亚砜(DMSO)和环丁砜等。
上述生产方法(c)也可以在酸结合剂存在下进行。可用的酸结合剂的实例如下:无机碱例如碱金属或碱土金属的氢氧化物、碳酸盐和碳酸氢盐如碳酸氢钠、碳酸氢钾、碳酸钠、碳酸钾、氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙;有机碱例如叔胺、N,N-二烷基苯胺和吡啶类,诸如三乙胺、1,1,4,4-四甲基乙二胺(TMEDA)、N,N-二甲基苯胺、N,N-二乙基苯胺、吡啶、4-二甲氨基吡啶(DMAP)、1,4-二氮杂双环[2.2.2]辛烷(DABCO)和1,8-二氮杂双环[5.4.0]十一-6-烯(DBU)。
生产方法(c)的反应可以在很宽的温度范围内进行。但一般可使用约-70~约150℃的反应温度,优选约-10~约80℃。此外,反应优选应该在常压下进行,但也可任选地在升高或降低的压力下进行。
为了进行生产方法(c),例如,可以在稀释剂诸如二氯甲烷中在碱如4-(N,N-二甲基氨基)吡啶存在下使1摩尔式(IV)化合物与1-3摩尔式(VI)化合物反应,由此得到式(I)的目的化合物。
在进行上述方法(d)时,可以用任何惰性溶剂作为合适的稀释剂。
这样稀释剂的实例有脂族、环脂族或芳香族的、任选被氯代的烃类诸如戊烷、己烷、环己烷、石油醚、石油英、苯、甲苯、二甲苯、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、氯苯、二氯苯等;醚类诸如乙醚、甲乙醚、异丙醚、丁醚、二噁烷、二甲氧基乙烷(DME)、四氢呋喃(THF)、二亚甲基二醇二甲醚等;酮类诸如丙酮、甲乙酮(MEK)、甲基异丙基酮、甲基异丁基酮(MIBK)等;腈类诸如乙腈、丙腈等;酯类诸如乙酸乙酯、乙酸戊酯等;酰胺类诸如二甲基甲酰胺(DMF)、二甲基乙酰胺(DMA)、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑烷酮、六甲基磷酸三酰胺(HMPA)等;以及砜类和亚砜类诸如二甲基亚砜(DMSO)、环丁砜等;以及碱诸如吡啶。
本发明方法(d)优选在酸结合剂存在下进行。这样的酸结合剂的实例可提及的如下:无机碱,包括碱金属或碱土金属的氢氧化物、碳酸盐和碳酸氢盐如碳酸氢钠、碳酸氢钾、碳酸钠、碳酸钾等;无机碱金属氨基化物,包括氨基锂、氨基钠、氨基钾等;有机碱,包括烷氧基化物、叔胺、N,N-二烷基苯胺和吡啶类,诸如三乙胺、三丁胺、1、1,4,4-四甲基乙二胺(TMEDA)、N,N-二甲基苯胺、N,N-二乙基苯胺、吡啶、4-二甲氨基吡啶(DMAP)、1,4-二氮杂双环[2.2.2]辛烷(DABCO)、1,8-二氮杂双环[5.4.0]十一-7-烯(DBU)等。
在上述方法(d)中,反应温度可以在很宽范围内变化。通常,反应在大约-70℃~大约150℃的温度下进行,优选-10℃~大约100℃的温度。此外,反应在常压下进行,但也可以使用较高的或较低的压力。
当进行本发明的上述方法(d)时,例如在稀释剂诸如四氢呋喃中在酸结合剂诸如碳酸氢钠存在下就每摩尔式(VII)化合物使用大约1-5摩尔式(VIII)化合物,以获得所希望的化合物。
上述生产方法(e)和(f)的反应可以在适当的稀释剂中进行。作为这样的稀释剂,可提及的是水和任选的惰性有机溶剂如脂族、环脂族或芳香烃类(它们可任选地被氯代)诸如戊烷、己烷、环己烷、石油醚、石油英、苯、甲苯、二甲苯、二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷、氯苯和二氯苯;醚类诸如乙醚、甲乙醚、异丙醚、丁醚、二噁烷、二甲氧基乙烷(DME)、四氢呋喃(THF)和二甘醇二甲醚(DGM);腈类诸如乙腈、丙腈和丙烯腈;以及醇类诸如甲醇、乙醇、异丙醇、丁醇和乙二醇。
生产方法(e)的反应可以在很宽的温度范围内进行。但一般可使用约-30~约150℃的反应温度,优选约-20~约100℃。此外,反应优选应该在常压下进行,但也可任选地在升高或降低的压力下进行。
为了进行生产方法(e),例如,可以在稀释剂诸如甲醇中使1摩尔式(IX)化合物与1-10摩尔氧化剂反应,由此得到式(I)的目的化合物。
生产方法(f)的反应可以在很宽的温度范围内进行。但一般可使用约-70~约150℃的反应温度,优选约-10~约100℃。此外,反应优选应该在常压下进行,但也可任选地在升高或降低的压力下进行。
为了进行生产方法(f),例如,可以在稀释剂诸如二氯甲烷中使1摩尔式(X)化合物与1-3摩尔氧化剂反应,由此得到式(I)的目的化合物。
本发明化合物可用来防治很宽范围内的各种害虫,尤其是有害的吮乳昆虫、叮咬昆虫和其它植物寄生害虫以及储谷中的害虫和卫生方面害虫,本发明化合物可作为防治这些害虫的杀虫剂。
所述害虫的实例如下:
作为昆虫,可提及的是来自鞘翅目的害虫,例如绿豆象、玉米象(Sitophilus zeamais)、赤拟谷盗、Epilachna vigintioctomaculata、细胸叩甲、Anomala rufocuprea、马铃薯甲虫、条叶甲(Diabrotica spp.)、Monochamus alternatus、稻象甲(Lissorhoptrus oryzophilus)和欧洲竹粉蠹(Lyctus bruneus);来自鳞翅目的害虫,例如,舞毒蛾、天幕毛虫(Malacosoma neustria)、菜青虫、斜纹夜蛾(Spodoptera litura)、甘蓝夜蛾、二化螟、Pyrausta nubilalis、Ephestia cautella、茶小卷蛾(Adoxophyes orana)、苹果蠹蛾、Agrotis fucosa、Galleria mellonella、小菜蛾、美洲菸夜蛾和Phyllocnistis citrella;来自半翅目的害虫,例如,黑尾叶蝉、稻褐飞虱、康氏粉蚧、矢尖蚧、桃蚜、苹果蚜、棉蚜、萝卜蚜、梨花网蝽、Nezara spp.、Cimex lectularius、温室白粉虱和Psylla spp.;来自直翅目的害虫,例如,德国小镰、美洲大镰、Gryllotralpa africana和热带飞蝗;来自等翅目的害虫,例如,Deucotermes speratus和Coptoternes formosanus;以及来自双翅目的害虫,例如,家蝇、Aedes aegypti、Hylemia platura、Culex pipiens、Anopheles sinensis和Culex tritaeniorhynchus。
作为螨,可提及的是例如Tetranychus kanzawai、棉红蜘蛛、Panonychus citri、Aculops pelekassi和Tarsonemus spp.。
作为线虫,可提及的有例如Meloiaogyne incognita、Bursaphelenchus xylophilus、Aphelenchoides besseyi、Heteroderaglycines和Pratylenchus spp.。
此外,在兽医药学领域内,本发明新化合物可以有效地防治各种有害的动物寄生虫(内寄生虫和外寄生虫),诸如昆虫和肠虫。这样的动物寄生虫的实例包括下列害虫:
作为昆虫,可提及的是例如Gastrophilus spp.、Stomoxys spp.、Trichodectes spp.、Rhodnius spp.和Ctenocephalides spp.。
作为螨,可提及的是例如Ornithodoros spp.、Ixodes spp.和Boophilus spp.。
在本说明书中,“杀虫剂”是具有防治上述提到的所有害虫的作用的物质的统称。
在用作杀虫剂时,可以将式(I)活性化合物转化成常规制剂,诸如溶液、可湿性粉剂、悬浮剂、粉剂、泡沫剂、糊剂、片剂、粒剂、气雾剂、浸渍了活性化合物的天然和合成材料、非常细的在聚合物质中的胶囊以及涂布种子用的组合物,此外还可以是与燃烧装置诸如熏蒸筒、熏蒸罐和熏蒸管等一起用的制剂,以及ULV冷雾和热雾制剂。
这些制剂可用已知方法制备,例如将活性化合物与增充剂混合,增充剂为液体溶剂、加压液化气体和/或固体载体,任选地与表面活性剂即乳化剂和/或分散剂和/或生泡剂一起使用。优选使用表面活性剂。
作为液体溶剂或载体,合适的主要为:芳香烃如二甲苯、甲苯或烷基萘;氯代芳香烃或氯代脂肪烃如氯苯类、氯乙烯类或二氯甲烷;脂肪烃如环己烷或烷属烃,例如矿物油馏分;醇类如丁醇或乙二醇,以及其醚类和酯类;酮类,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂如二甲基甲酰胺和二甲亚砜;以及水。在用水作为液体溶剂或载体的情况下,可用有机溶剂作为辅助溶剂。
液化的气态稀释剂或载体是指在常温常压下是气态的液体,例如气雾剂抛射剂如丁烷、丙烷、氮、二氧化碳和卤代烃类。
作为固体稀释剂或载体,合适的有例如粉碎的天然矿物,如高岭土、陶土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和粉碎的合成矿物,如高分散硅酸、氧化铝和硅酸盐。
作为供粒剂用的固体载体,适合的有:例如压碎和碎片化的天然岩石如方解石、大理石、浮石和海泡石、白云石,以及无机和有机粉的合成颗粒,和有机材料如锯木屑、椰壳、玉米棒和烟茎的颗粒。
作为乳化剂和/或发泡剂,适合的有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚例如烷基芳基聚乙二醇醚,烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白水解产物。
作为分散剂,适合的有:例如木质素亚硫酸盐废液和甲基纤维素。
制剂如粉剂、粒剂和乳剂中可以采用粘合剂,可提及的适用的粘合剂的例子有如羧甲基纤维素和天然和合成的聚合物如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯。
可使用着色剂如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素诸如金属例如铁、镁、硼、铜、钴、钼和锌的盐。
通常制剂可含有0.1至95%、优选0.5至90%重量的活性化合物。
本发明的式(I)活性化合物可以存在在其市售的制剂中,并且可以是作为与其它活性化合物诸如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节物质或除草剂的混合物而用所述制剂制成的使用形式。上述杀虫剂包括例如有机磷酸酯类、氨基甲酸酯类、羧酸酯类、氯代烃类和由微生物产生的杀虫物质。
本发明的式(I)活性化合物还可以作为与增效剂的混合物存在。增效剂是增强活性化合物作用但所加入的增效剂本身不必要是活性的化合物。
在其使用形式中本发明式(I)活性化合物的含量可在很宽范围内变化。在其使用形式中本发明式(I)活性化合物的浓度一般可为0.0000001-100%重量,优选0.00001-1%重量。
本发明式(I)化合物可以以适用于所述使用形式的常规方法如通过喷雾和散布来使用。可用式(I)化合物处理土壤和叶子。在系统易位(systemic translocation)后它们也具有活性。此外,本发明的活性化合物对石灰物质的碱性具有很好的稳定性并在木头和土壤上具有优良的残留作用。这样,它们可极其有效地防治卫生方面的害虫和储谷中的害虫。
下列实施例具体说明本发明,但不应将它们视为是对本发明范围的限制。
合成实施例1
将4-氯-4’-甲硫甲基二苯酮(9.3g)、水合肼(6ml)和乙酸(3ml)的乙醇溶液(50ml)加热回流20小时。减压下蒸掉溶剂,然后用二氯甲烷稀释得到的油状物,并依次用5%氢氧化钠水溶液、水和饱和氯化钠水溶液洗涤,接着用无水硫酸镁干燥。蒸掉溶剂,得到了4-氯-4’-甲硫甲基二苯酮腙(7.1g),为异构体混合物(顺式/反式形式=约1∶1)。nD 201.6350。
合成实施例2
将4-氟-4’-甲硫甲基二苯酮(7.8g)、肼基甲酸乙酯(9.4g)和乙酸(9ml)的乙醇溶液(100ml)加热回流20小时。减压下蒸掉溶剂,然后用二氯甲烷稀释得到的油状物,并依次用5%氢氧化钠水溶液、水和饱和氯化钠水溶液洗涤,接着用无水硫酸镁干燥。蒸掉溶剂,得到了4-氟-4’-甲硫甲基二苯酮乙氧羰基腙(6.4g),为异构体混合物。nD 201.6040。
合成实施例3
将4-氯-4’-甲基亚磺酰甲基二苯酮(5.8g)、肼基甲酸乙酯(6.3g)和对甲苯磺酸吡啶鎓(O.1g)的乙醚溶液(100ml)加热回流6小时。冷却至室温后,将反应混合物倒入冰水中,过滤收集沉出的结晶,依次用碳酸氢钠水溶液和水洗涤。空气干燥后,得到4-氯-4’-甲基亚磺酰甲基二苯酮乙氧羰基腙(6.4g),为异构体混合物。M.p.65-70℃。
按合成实施例3中所述的同样方式进行反应,只是用4-氯-4’-甲基磺酰基甲基二苯酮(6.2g)代替4-氯-4’-甲基亚磺酰基甲基二苯酮,由此得到了4-氯-4’-甲基磺酰基甲基二苯酮乙氧羰基腙(6.7g),为异构体混合物。M.p.166-169℃。
合成实施例4
将4-氯-4’-甲硫甲基二苯酮(8.3g)、肼基甲酸乙酯(10g)和对甲苯磺酸吡啶鎓(0.1g)的乙醚溶液(100ml)加热回流16小时。冷却至室温后,将反应混合物倒入冰水中,过滤收集沉出的结晶,用水洗涤。空气干燥后,得到4-氯-4’-甲硫甲基二苯酮乙氧羰基腙(9.4g),为异构体混合物。M.p.105-109℃。
将该混合物(1.0g)用硅胶柱层析纯化(洗脱剂:正己烷∶乙酸乙酯=9∶1),由第一洗脱部分得到了0.24g异构体A,M.p.106-107℃;由第二洗脱部分得到了0.56g异构体B,M.p.117-120℃。
在冰冷却下向4-氯-4’-甲硫甲基二苯酮腙(1.5g)和4-(N,N-二甲氨基)吡啶(1.2g)的二氯甲烷溶液(30ml)中滴加氯甲酸异丁酯(0.8g),然后在室温下搅拌20小时。再依次用2N盐酸、水和饱和氯化钠水溶液洗涤反应混合物,用无水硫酸镁干燥、蒸掉溶剂后,通过硅胶柱层析纯化粗产物(洗脱剂:乙酸乙酯∶正己烷=1∶4),得到4-氯-4’-甲硫甲基二苯酮异丁氧基羰基腙的异构体混合物(0.5g)。nD 201.6103。
合成实施例6
向4-氯4’-甲硫甲基二苯酮(0.5g)的乙腈溶液(10ml)中加入异氰酸4-三氟甲氧基苯酯(0.3g),在室温下搅拌10小时。减压下蒸掉溶剂后,残留物用乙醇重结晶,得到4-氯-4’-甲硫甲基二苯酮4-(4-三氟甲氧基苯基)氨基脲(0.5g)。M.p.179-183℃。
合成实施例7
在氩气气氛下向4-氯-4’-甲硫甲基二苯酮乙氧羰基腙(3.6g)的二甲基甲酰胺溶液(10ml)中加入60%氢化钠矿物油分散体(0.4g),并在室温下搅拌至停止放出氢气为止。然后加入碘甲烷(3g),在室温下搅拌16小时。将反应混合物倒入冰水中,向其中加入乙酸乙酯。然后分离有机层,依次用2N盐酸水溶液、水和饱和氯化钠水溶液洗涤,接着用无水硫酸钠干燥。蒸掉溶剂后,通过硅胶柱层析纯化所得粗产物(洗脱剂:正己烷∶乙酸乙酯=5∶1),得到4-氯-4’-甲硫甲基二苯酮N’-乙氧羰基-N’-甲基腙(1.5g)。nD 201.6039。
下表7列出了上述合成实施例1-7中所合成的化合物以及以与上述合成实施例1-7中所述方法相同的方法合成的化合物。化合物1-30和33-216是异构体混合物(反式形式/顺式形式)。化合物31和32是纯异构体。
表7
R1 R2 R3 n R4 R5 R6 R7 折射率
1 Br H CH3 0 H H H H nD 20=1.6890
2 Cl H CH3 0 H H H H nD 20=1.6350
3 Cl H CH3 1 H H H H 45-51℃
4 Cl H CH3 2 H H H H 124-130℃
5 Br H CH3 0 CO2C2H5 CH2OCH3 H H nD 20=1.5972
6 Br H CH3 0 CO2C2H5 CH2SCH3 H H nD 20=1.6032
7 Br H CH3 0 CO2C2H5 CH3 H H nD 20=1.6186
8 Br H CH3 0 CO2C2H5 H H H 98-103℃
9 Br H CH3 0 CO2CH3 CH2OCH3 H H nD 20=1.5984
10 Br H CH3 0 CO2CH3 H H H 125-135℃
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率
11 Br H C2H5 0 CO2CH3 H H H nD 20=1.6267
12 Br H CH2CF3 0 CO2C2H5 H H H nD 20=15824
13 Br H CH2CHF2 0 CO2C2H5 H H H nD 20=1.5941
14 Br H CH3 1 CO2CH3 H H H 58-63℃
15 Br H CH3 2 CO2CH3 H H H 179-183℃
16 Cl H CH3 0 CO2C2H5 CH2CO2C2H5 H H nD 20=1.5763
17 Cl H CH3 0 CO2C2H5 CH2OC2H5 H H nD 20=1.5773
18 Cl H CH3 0 CO2C2H5 CH2OCH3 H H nD 20=1.5903
19 Cl H CH3 0 CO2C2H5 CH2SCH3 H H nD 20=1.6088
20 Cl H CH3 0 CO2C2H5 CH3 H H nD D 20=1.6039
21 Cl H CH3 0 CO2C2H5 CHF2 H H nD 20=1.5824
23 Cl H CH3 0 CO2C2H5 COC3H7-i H H nD 20=1.5740
24 Cl H CH3 0 CO2C2H5 COC3H7-n H H nD 20=1.5830
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率25 Cl H CH3 0 CO2C2H5
H H nD 20=1.599626 Cl H CH3 0 CO2C2H5
H H nD 20=1.603627 Cl H CH3 0 CO2C2H5 COC6H5 H H nD 20=1.617528 Cl H CH3 0 CO2C2H5 COCH=CHC6H5 H H nD 20=1.631829 Cl H CH3 0 CO2C2H5 COCH3 H H nD 20=1.601530 Cl H CH3 0 CO2C2H5 H H H 105-109℃31 Cl H CH3 0 CO2C2H5 H H H 106-107℃32 Cl H CH3 0 CO2C2H5 H H H 117-120℃33 Cl H CH2CN 0 CO2C2H5 H H H 105-106.5℃34 Cl H CH3 0 CO2C2H5 n-C3H7 H H nD 20=1.587235 Cl H CH3 0 CO2CH2CF3 H H H nD 20=1.595436 Cl H CH3 0 CO2CH2CH=CH2 H H H nD 20=1.622937 Cl H CH3 0 CO2CH2CH2Cl H H H 98-101℃38 Cl H CH3 0 CO2CH3 CH2OCH3 H H nD 20=1.602939 Cl H CH3 0 CO2CH3 H H H 136-140℃40 Cl H CH2CN 0 CO2CH3 H H H 38.5-147.5℃41 Cl H CH3 0 CO2C3H7-i H H H 115-119℃
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率42 Cl H CH3 0 CO2C4H9-i H H H nD 20=1.610343 Cl H CH3 0 CO2C3H7-n H H H 94-98℃44 Cl H CH3 0 CO2C4H9-n H H H 79-83℃45 Cl H CH3 0 CO2C5H11-n H H H 86-89℃46 Cl H CH3 0 CO2C6H13-n H H H 63.5-66.5℃47 Cl H CH3 0 CO2C4H9-t H H H 52-55℃48 Cl H CH3 0 CO2C2H5 H H 3-Br 124-125℃49 Cl H CH3 0 CO2C2H5 H H 3-CH3 nD 20=1.614750 Cl H C2H5 0 CO2C2H5 H H H 77-78.5℃51 Cl H C2H5 0 CO2CH2CF3 H H H nD 20=1.573252 Cl H C2H5 0 CO2CH3 H H H 87-92℃53 Cl H C3H7-i 0 CO2C2H5 H H H 125-127℃54 Cl H C3H7-i 0 CO2CH3 H H H nD 20=1.626755 Cl H C3H7-n 0 CO2C2H5 H H H 70-71℃56 Cl H C3H7-n 0 CO2CH3 H H H 98-101℃57 Cl H C4H9-n 0 CO2C2H5 H H H nD 20=1.590858 Cl H CF3 0 CO2C2H5 H H H nD 20=1.577259 Cl H CH2C≡CH 0 CO2C2H5 H H H 118-124℃60 Cl H CH2C≡CH 0 CO2CH3 H H H 127-137℃61 Cl H CH2CF3 0 CO2C2H5 H H H nD 20=1.583862 Cl H CH2CF3 0 CO2CH3 H H H nD 20=1.5603
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率63 Cl H CH2CH2CH2Cl 0 CO2C2H5 H H H 77-79℃64 Cl H CH2CH2F 0 CO2C2H5 H H H 75.5-77.5℃65 Cl H CH2CH2F 0 CO2CH3 H H H 78-82℃66 Cl H CH2CH=CH2 0 CO2C2H5 H H H 67-81℃67 Cl H CH2CHF2 0 CO2C2H5 H H H nD 20=1.576268 Cl H CH2CHF2 0 CO2CH3 H H H nD 20=1.583869 Cl H CHF2 0 CO2C2H5 H H H 85-88.5℃70 Cl H CHF2 0 CO2CH3 H H H 85-88℃71 Cl H CH3 1 CO2C2H5 H H H 65-70℃72 Cl H CH3 1 CO2CH3 H H H 60-75℃73 Cl H C2H5 1 CO2C2H5 H H H nD 20=1.583574 Cl H C3H7-n 1 CO2CH3 H H H 69.5-72℃75 Cl H CH2CF3 1 CO2C2H5 H H H 64.5-72℃76 Cl H CHF2 1 CO2C2H5 H H H 57-69℃77 Cl H CHF2 1 CO2CH3 H H H 无定形78 Cl H CH3 2 CO2C2H5 H H H 166-169℃79 Cl H CH3 2 CO2CH3 H H H 205-208℃80 Cl H CH3 2 CO2C4H9-t H H H 190-193℃81 Cl H C2H5 2 CO2C2H5 H H H 93-95℃82 Cl H C2H5 2 CO2CH3 H H H 70-78℃83 Cl H C3H7-i 2 CO2CH3 H H H nD 20=1.593084 Cl H C3H7-n 2 CO2CH3 H H H 131-138℃85 Cl H CH2CHF2 2 CO2C2H5 H H H 147-149℃86 Cl CH3 CH3 0 CO2C2H5 H H H nD 20=1.6205
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率87 Cl CH3 CH3 0 CO2CH3 H H H nD 20=1.603288 Cl CH3 CH3 1 CO2C2H5 H H H 48-53℃89 Cl CH3 CH3 2 CO2C2H5 H H H 115-117℃90 Cl C2H5 CH3 0 CO2C2H5 H H H nD 20=1.605291 Cl n-C3H7 CH3 0 CO2C2H5 H H H nD 20=1.599592 Cl H CH3 0 CO2C2H5 H 2-Cl H 52-55℃93 Cl H CH3 0 CO2CH3 H 2-Cl H 61-64℃94 Cl H CH3 0 CO2C2H5 H 3-Cl H 135-143℃95 F H CH3 0 CO2C2H5 H H H nD 20=1.604096 F H CH3 0 CO2C2H5 H 3-F H nD 20=1.580397 I H CH3 0 CO2C2H5 H H H 128-130℃98 Cl H CH3 0 COCH3 H H H 124-128℃99 Cl H CH3 0 COC2H5 H H H 103-113℃100 Cl H CH3 0 COC3H7-n H H H 100-104℃101 Cl H CH3 O COC4H9-n H H H 50-55℃102 Cl H CH3 0 COC4H9-t H H H 86-94℃103 Cl H CH3 0
H H H 122-124℃104 Cl H CH3 0
H H H 114-116℃
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率105 Cl H CH3 0
H H H 144-145℃106 Cl H CH3 0 COC6H5 H H H 126-130℃107 Cl H CH3 0 COCH2CH2CH2CH2Cl H H H 100-103℃108 Cl H CH3 0 COCH2CH2CH2Cl H H H 83-88℃109 Cl H CH3 0 COCH2CH2Cl H H H 98-101℃110 Cl H CH3 1 COC3H7-n H H H 140-145℃111 Cl H CH3 2 COC3H7-n H H H 121-131℃112 Cl H CH3 0
H H H 145-148℃113 Cl H CH3 0 CONH2 H H H 167-176℃114 Cl H CH3 0 CONHC2H5 H H H nD 20=1.6080115 Cl H CH3 0
H H H 179-183℃116 Cl H CH3 0 CONHCH2CH2Cl H H H 126-135℃117 Cl H CH3 0 CSNH2 H H H 169-172℃118 Cl H CH3 0
H H H nD 20=1.6824119 Cl H CH3 2 CONHC2H5 H H H 186-189℃120 Cl H s-C4H9 0 CO2C2H5 H H H 晶状物和油状物的混合物
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率121 Cl H CH3 0
H H H 121-122.5℃122 Cl H CH3 0
H H H nD 20=1.6543123 Cl H CH3 0 COCH2CO2C2H5 H H H nD 20=1.6148124 Cl H CH3 0 CO2C2H5 i-C3H7 H H nD 20=1.5799125 Cl H CH3 0
H H H nD 20=1.6081126 Cl H CH3 0 CO2C5H11-neo H H H 144-146℃127 Cl H CH3 0 CO2CH2CH(CH3)C2H5 H H H nD 20=1.6061128 Cl H CH3 0 CO2CH2C(CH3)=CH2 H H H nD 20=1.6195129 Cl H CH3 0 CO2C2H5 H 3-F H nD 20=1.6084130 Cl H CH3 0 CO2C2H5 H 2-F H 73-76℃131 Cl H CH3 0 CO2C2H5 CH2C6H5 H H nD 20=1.6250132 Cl H CH3 0 CO2C2H5
H H nD 20=1.5939133 Cl H CH3 0 COC3H7-n CH3 H H nD 20=1.6139
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率134 Cl H (CH2)3F 0 CO2C2H5 H H H 69.5-77.5℃135 Cl H CH2CF3 2 CO2C2H5 H H H 147.5-154.5℃136 Cl H CH=CH2 0 CO2C2H5 H H H nD 20=1.6233137 Cl H CH2Cl 0 CO2C2H5 H H H 102-103℃138 Cl H CH3 0 t-C4H9 H H H nD 20=1.5935139 Cl H CH3 0 CO2CH3 COC3H7-n H H nD 20=1.5773140 Cl H C2H5 0 CO2C3H7-n H H H nD 20=1.5927141 Cl H C2H5 0 CO2C3H7-i H H H 93.5-101℃142 Cl H CH3 0 COCH2CN H H H 118-125.5℃143 Br H CH3 2 CO2C2H5 H H H 159-161℃144 Cl H CH3 2 CH3 H H H 无定形145 Cl H CH3 2 CH3 CH3 H H 133.5-136℃146 Cl H CH3 2 C6H5 H H H 172.5-180.5℃147 Br H C2H5 0 CO2C3H7-n H H H nD 20=1.6162148 Cl H C2H5 0 CO2C4H9-s H H H nD 20=1.5944149 Cl H C2H5 0 COCH2OCH3 H H H 86-95℃150 Cl H CH=CH2 0 CO2CH3 H H H nD 20=1.6282151 Cl H C2H5 0 CO2C4H9-i H H H nD 20=1.5914152 Cl H C2H5 0
H H H nD 20=1.5878
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率153 Cl H CH3 2 C6H5 CH3 H H 63-66.5℃154 Cl H C2H5 0
H H H nD 20=1.5843155 Cl H CH3 0 CO2C2H5 COC2H5 H H nD 20=1.5756156 Cl H C2H5 0 CO2C3H7-n COC3H7-n H H nD 20=1.5681157 Cl H CH2F 0 CO2C2H5 H H H nD 20=1.6051158 Cl H CH3 0 CO2C2H5 C2H5 H H nD 20=1.5931159 Cl H C2H5 0 CO2C2H5 C3H5-i H H nD 20=1.5694160 Br H CH3 0 CO2C2H5 C3H5-i H H nD 20=1.5956161 Cl H CH3 0 COCH2OCH3 CO2C2H5 H H nD 20=1.5850162 Cl H CH3 0
H H H 109-114.5℃163 Cl H CH3 0 CO2C4H9-s H H H nD 20=1.5901164 Br H C2H5 0 CO2C2H5 H H H nD 20=1.6231165 Cl H C2H5 0 CO2CH2Si(CH3)3 H H H nD 20=1.5811166 Cl H CH2OC2H5 0 CO2C2H5 H H H 70-72℃167 Cl H CH2OCH3 0 CO2CH3 H H H nD 20=1.6141168 Cl H CH2Si(CH3)3 0 CO2C2H5 H H H 74-75℃
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率169 Cl H CH3 0 CO2CH2CH2OCH3 H H H nD 20=1.6336170 Cl H CH3 0 H CO2CH2Si(CH3)3 H H nD 20=1.5702171 Cl H CH3 0 H
H H nD 20=1.6133172 Cl H n-C3H7 0 H -CO2C3H7-n H H nD 20=1.6018173 Cl H C2H5 1 H CO2CH3 H H 156.5-169℃174 Cl H C2H5 1 H CO2CH2CF3 H H 101.5-107℃175 Cl H n-C3H7 1 H CO2C3H7-n H H nD 20=1.5681176 Br H C2H5 1 H CO2CH3 H H 163-168.5℃177 Br H C2H5 1 H CO2C2H5 H H 131-135℃178 Cl H CH3 0 H CO(CH2)5Br H H nD 20=1.6021179 Cl H CH3 0 H
H H 117-120.5℃180 Cl H CH3 0 n-C4H9 CO2C2H5 H H nD 20=1.5828181 Cl H CH3 0 COC4H9-n CO2C2H5 H H nD 20=1.5770182 Cl H C2H5 0 C2H5 CO2C2H5 H H nD 20=1.5822183 Br H C2H5 0 C2H5 CO2C3H7-n H H nD 20=1.5870184 Cl H CH3 1 C2H5 CO2C2H5 H H nD 20=1.5834
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率185 Cl H CH3 0 H COCO2C2H5 H H 118-123℃186 Cl H CH3 0 CO2C2H5 CH2CH=CH2 H H nD 20=1.5962187 Cl H CH3 0 CO2C2H5 CH2C≡CH H H nD 20=1.5944188 Cl H CH3 0 CO2C2H5 CH2CH2F H H nD 20=1.5837189 Cl H CH3 0 CO2C2H5 C2H5 H H 30-38℃190 Cl H C2H5 0 CO2C2H5 CH3 H H nD 20=1.6021191 Cl H C2H5 0 CO2C2H5 C2H5 H H nD 20=1.5922192 Cl H C2H5 1 CO2C2H5 CH3 H H nD 20=1.5930193 Cl H C2H5 2 CO2C2H5 CH3 H H nD 20=1.5622194 Cl H C2H5 1 CO2C2H5 C2H5 H H nD 20=1.5852195 Cl H C2H5 2 CO2C2H5 C2H5 H H nD 20=1.5854196 Cl H C2H5 1 CO2CH3 CH3 H H nD 20=1.6182197 Cl H C2H5 2 CO2CH3 CH3 H H 58-62℃198 Br H CH3 0 CO2C2H5 C2H5 H H nD 20=1.6020199 Br H CH3 1 CO2C2H5 C2H5 H H nD 20=1.5950200 Br H CH3 2 C2H5 CO2C2H5 H H nD 20=1.5880201 Cl H CH3 0 CO2C2H5 CO2CH3 H H nD 20=1.5852202 Cl H CH3 1 CO2CH3 CO2C2H5 H H nD 20=1.5858203 Cl H CH3 0 CO2C2H5 CO2C2H5 H H nD 20=1.5728
表7(续)化合物编号 R1 R2 R3 n R4 R5 R6 R7 熔点或折射率204 Cl H CH3 0 CO2C4H9-i C2H5 H H nD 20=1.5783205 Cl H CH3 0 CO2C2H5 (CH2)5CH3 H H nD 20=1.5749206 Cl H CH3 0 CO2CH2CF3 C2H5 H H207 Cl H CH3 0 COC3H7-i H H H nD 20=1.6528208 Cl H CH3 1 CO2C4H9-n H H H nD 20=1.5944209 Cl H C2H5 1 CO2C4H9-i H H H nD 20=1.5763210 Cl H CH3 0 CO2C2H5 CH2CN H H nD 20=1.5977211 Cl H C2H5 0 CO2C2H5 COC6H5 H H nD 20=1.5990212 Cl H C2H5 1 CO2C2H5 COC6H5 H H nD 20=1.5890213 Cl H C2H5 2 CO2C2H5 COC6H5 H H nD 20=1.5980214 Cl H CH3 0 COCH3 C2H5 H H nD 20=1.6140215 Cl H C2H5 2 COC3H7-n C2H5 H H nD 20=1.5808216 Cl H CH3 0 COC6H5 COCH3 H H nD 20=1.6308
中间体的合成
向4-溴甲基-4’-氟二苯酮(20g)的乙腈溶液(200ml)中加入15%甲硫醇钠溶液(60ml)并将混合物加热回流6小时。将反应混合物恢复到室温,加入水(500ml)和甲苯(300ml)。分离有机层,然后依次用2N氢氧化钠水溶液和水洗涤,并用无水硫酸镁干燥。蒸掉溶剂,通过硅胶柱层析纯化粗产物(洗脱剂:正己烷∶乙酸乙酯=9∶1),得到4-氟-4’-甲硫甲基二苯酮(17g)。nD 201.6375。
在-78℃,向4-溴氟苯(1.75g)的乙醚溶液(30ml)中加入1.6M正丁基锂己烷溶液(6.3ml),并将混合物在同样的温度下搅拌1小时。在-78℃向其中滴加4-甲硫甲基苄腈(1.63g)的乙醚溶液(10ml),并将混合物搅拌16小时,同时使混合物逐渐恢复到室温。向反应混合物中加入6N盐酸水溶液,并在室温下搅拌1小时,再加入乙醚(20ml)。分离有机层,用水洗涤,用无水硫酸镁干燥。蒸掉溶剂,通过硅胶柱层析纯化所得粗产物(洗脱剂:正己烷∶乙酸乙酯=9∶1),得到4-氟-4’-甲硫甲基二苯酮(1.12g)。nD 201.6375。
将S-(4-(4-氯苯甲酰基)苄基)硫脲鎓溴化物(3.3g)和碳酸钾(1.5g)溶于二甲基甲酰胺(20ml)中。加入氢氧化钾(1.0g)的甲醇溶液(10ml),并在室温下搅拌30分钟。向反应混合物中加入水(100ml)和甲苯(100ml)。分出有机层,用水和饱和氯化钠水溶液洗涤,用无水硫酸镁干燥。蒸掉溶剂,通过硅胶柱层析纯化粗产物(洗脱剂:乙酸乙酯∶己烷=1∶9),得到4-氯-4’-乙硫甲基二苯酮(1.3g)。M.p.34-35℃。
按照与合成实施例10同样的方法,用溴二氟甲烷(3.9g)代替碘乙烷,得到了4-氯-4’-二氟甲硫甲基二苯酮(0.8g)。M.p.60-62℃。
按照与合成实施例10同样的方法,用三氟碘甲烷(5.9g)代替碘乙烷,得到了4-氯-4’-三氟甲硫甲基二苯酮(0.4g)。M.p.78-79℃。
合成实施例11
(合成实施例10用的起始原料的合成)
将4-溴甲基-4’-氯二苯酮(31g)和硫脲(10g)的丙酮溶液(500ml)加热回流30分钟。然后过滤收集沉出的结晶,用丙酮洗涤,得到S-(4-(4-氯苯甲酰基)苄基硫脲鎓溴化物(33g)。M.p.76-78℃。
在-78℃,向由1.6M正丁基锂己烷溶液(12.5ml)和二异丙胺(2.1g)制备的二异丙基氨基锂的四氢呋喃溶液(30ml)中加入4-氯-4’-甲硫甲基二苯酮(2.8g)的四氢呋喃溶液(10ml)。将混合物在同样的温度下搅拌30分钟。然后在-78℃向其中加热碘乙烷(3.0g),将混合物搅拌6小时,同时使混合物逐渐恢复到室温。反应完成后,用5%氯化铵水溶液和饱和氯化钠水溶液洗涤混合物,用无水硫酸镁干燥。蒸掉溶剂,通过硅胶柱层析纯化所得粗产物(洗脱剂:正己烷∶乙酸乙酯=4∶1),得到了4-氯-4’-(1-甲硫丙基)二苯酮(0.3g),为油状物。
1H-NMR(90MHz,CDCl3)(0.93,3H,t)(1.88,3H,s)(1.96,2H,m)(3.63,1H,t)(7.27-7.80,8H,m)。
合成实施例13
向4-(4-氯苯甲酰基)苄基硫氰酸酯(1.5g)和苄基硫氰酸酯(1.5g)的吡啶溶液(30ml)中加入锌粉(0.4g),并于三氟碘甲烷气氛下于室温下搅拌24小时。然后加入甲苯(50ml),滤掉锌粉。用2N HCl水溶液洗涤滤液(30ml三次)并用无水硫酸镁干燥。蒸掉溶剂,用柱层析(正己烷∶乙酸乙酯=6∶1)纯化残留物,得到4-氯-4’-三氟甲硫甲基二苯酮(0.5g)。M.p.78-79℃。
将4-氯-4’-(2-氯乙硫基甲基)二苯酮(4.9g)和1,8-二氮杂双环[5.4.0]十一-7-烯(4.3g)在100ml甲苯中的混合物在80℃搅拌3小时。然后,用2N盐酸水溶液和水洗涤混合物,再用无水硫酸钠干燥。减压下蒸掉溶剂,得到4-氯-4’-乙烯基硫基甲基二苯酮(4.3g)。nD 201.6363。
合成实施例15
向4-氯-4’-甲硫甲基二苯酮(8.3g)的乙酸溶液(30ml)中加入30%的过氧化氢水溶液(3.5ml)。将温度保持在10℃搅拌混合物2小时。向反应液中加入水(200ml)和甲苯(200ml),然后分出有机层,依次用水、碳酸氢钠水溶液和饱和氯化钠水溶液洗涤,再用无水硫酸镁干燥。蒸掉溶剂,通过硅胶柱层析纯化粗产物(洗脱剂:丙酮∶正己烷=50∶50),得到4-氯-4’-甲基亚磺酰基甲基二苯酮(5.3g)。M.p.125-128℃。
将4-氯-4’-甲基亚磺酰基甲基二苯酮(2.9g)和间氯过苯甲酸(2.5g)溶于二氯甲烷中。将混合物在0℃搅拌12小时。滤出沉出的结晶后,依次用碳酸氢钠水溶液、5%硫代硫酸钠溶液和水洗涤滤液,再用无水硫酸镁干燥。蒸掉溶剂,通过硅胶柱层析纯化粗产物(洗脱剂:乙酸乙酯∶正己烷=1∶5),得到4-氯-4’-甲基磺酰基甲基二苯酮(1.8g)。M.p.173-174℃。
在室温下向4-氯-4’-甲硫甲基二苯酮(8.3g)的乙酸溶液(70ml)中加入30%过氧化氢水溶液(7ml),并将混合物在70℃搅拌6小时。将反应混合物倒入冰水中,过滤收集沉出的结晶,用碳酸氢钠水溶液和水洗涤,然后空气干燥,得到4-氯-4’-甲基磺酰基甲基二苯酮(4.3g)。M.p.173-174℃。
将4-氟-4’-甲基二苯酮(16g)、N-溴代琥珀酰亚胺(14.2g)和2,2’-偶氮双异丁腈(0.1g)的四氯化碳溶液(200ml)加热回流16小时。将混合物冷至室温后,过滤收集沉淀物,蒸掉溶剂,得到4-溴甲基-4’-氟二苯酮(20g)。M.p.73-75℃。
参考实施例2
在室温下向氯化铝(26g)的甲苯悬浮液(200ml)中滴加对氟苯甲酰氯(16g)的甲苯溶液(50ml)。然后在室温下将混合物搅拌20小时,再小心地倒入冰水中,向其中加入甲苯(200ml),分出有机层。依次用2N盐酸水溶液、水和饱和氯化钠水溶液洗涤,用无水硫酸钠干燥。减压下蒸掉溶剂,得到4-氟-4’-甲基二苯酮(16g),M.p.97-98℃。
参考实施例3
在室温下向4-氰基苄基溴(50g)的乙腈溶液(500ml)中加入15%甲硫醇钠盐(120ml),并加热回流6小时。冷却到室温后,向其中加入水(1升)和甲苯(1升)。分出有机层,依次用2N氢氧化钠水溶液和硫酸盐水溶液洗涤。蒸掉溶剂后,得到了4-甲硫甲基苄腈(38g)。nD 201.5821。
下表8列出了上述合成实施例8-17中合成的化合物以及以与合成实施例8-17所述方法相同的方法合成的化合物。
表8
R1 R6 R7 A 熔点或折射率Br H H CH2SC(=NH)NH2·HBr 225-231℃Cl H H CH(CH3)SC(=NH)NH2·HBr 158-159℃Cl H H CH2SC(=NH)NH2·HBr 76-78℃Cl H 2-Cl CH2SC(=NH)NH2·HBr 110-114℃Cl H 3-Cl CH2SC(=NH)NH2·HBr 198-201℃I H H CH2SC(=NH)NH2·HBr 196-210℃Cl H H CH2SCN 149-150℃Cl H H CH2S(CS)OC2H5 62-68℃Cl H H CH2S(CO)CH3 98-99℃Br H H CH2SC2H5 46-48℃Cl H H CH(CH3)SCH3 nD 201.6198Cl H H CH2SC2H5 34-35℃Cl H H CH2SC3H7-iso nD 201.6320Cl H H CH2SC3H7-n nD 201.6211Cl H H CH2SCF3 78-79℃Cl H H CH2SCH2C≡CH 80-81℃Cl H H CH2SCH2CF3 77-78℃Cl H H CH2SCH=CH2 nD 201.6363Cl H H CH2SCH2CH=CH2 nD 201.6368Cl H H CH2SCH2CH2Cl 65-67℃Cl H H CH2SCH2CH2F 44-45℃Cl H 3-Br CH2SCH3 nD 201.6502Cl H 3-CH3 CH2SCH3 nD 201.6345
表8(续)R1 R6 R7 A 熔点或折射率Cl H 2-CH3 CH2SCH3 nD 20=1.6324Cl H H CH2SCHF nD 201.6237Cl H H CH2SCHF2 60-62℃Cl H H CH2(SO2)CH3 173-174℃Cl H H CH2(SO)CH3 125-128℃Cl 2-Cl H CH2SCH3 nD 201.6369Cl 3-Cl H CH2SCH3 66-67℃F H H CH2SCH3 nD 201.6375F 3-F H CH2SCH3 nD 201.6306I H H CH2SCH3 89-91℃Cl H H CH2SCH2CN 87.5-88℃Cl H H CH2SCH2CHF2 59-60.5℃Cl H H CH2SCH2CH2CH2Cl nD 201.6113Br H H CH2SCH2CF3 79.5-81.5℃Br H H CH2SCH2CHF2 62-64℃Cl H H CH2SCH2CH2CH2F 39-40.5℃Cl H H CH2SCH2Si(CH3)3 95-100℃
生物试验实施例
试验溶液的制备
溶剂:3份重量的二甲苯
乳化剂:1份重量的聚氧乙烯烷基苯基醚
为了生产合适的活性化合物的制剂,将1份重量的活性化合物与所给出量的含给出量的乳化剂的溶剂混合,用水将混合物稀释至规定的浓度,由此制备试验溶液。
试验实施例1
(抗Spodoptera litura幼虫试验)
试验步骤:
将洋白菜(Brassica oleracea)的叶子浸在规定浓度的活性化合物的溶液中。溶液经空气干燥后,将处理过的叶子放到皮氏培养皿中,然后放入10只1/3龄期的斜纹夜蛾(Spodotera litura)的幼虫。将培养皿置于25℃的温室中。7天后,检查幼虫的死亡数目,计算百分致死率。重复试验两次,测定平均百分致死率。
结果:
化合物8、12、16、34、37、43、48、50、54、57、60、63、74、83、92、106、171、121、125、132、139、140、141、142、147、148、149、151、152、155、157、158、159、160、161、162、163、164、165、168、170、171、172、173、174、175和176在200ppm浓度时显示出100%致死率,而化合物1、5、22、29、33、40、47、49、68、75、79、87、100、111、113、116、123、130、133、135、136、137、143、144、145、150、154、156和169在100ppm浓度时显示出100%致死率。
试验实施例2
(抗Aulacophora femoralis试验)
试验步骤:
将黄瓜(Cucumis sativus)的叶子浸在规定浓度的活性化合物的溶液中。溶液经空气干燥后,将处理过的叶子放到皮氏培养皿中,然后放入10只1/2龄期的黄守瓜(Aulacophora femoralis)的幼虫。将培养皿置于25℃的温室中。7天后,检查幼虫的死亡数目,计算百分致死率。重复试验两次,测定平均百分致死率。
结果:
化合物3、7、15、18、23、25、31、36、39、44、51、58、59、61、65、73、77、78、84、85、91、93、96、98、101、103、109、114、115、119、120、126、129、131、133、135、136、140、145、148、150、152、154、156、163、167、169、170和172在200ppm浓度时显示出100%的致死率。
试验实施例3
(抗对苯甲酰脲类具有抗性的Plutella xylostella幼虫试验)
试验步骤:
将洋白菜(Brassica oleracea)的叶子浸在规定浓度的活性化合物的溶液中。溶液经空气干燥后,将处理过的叶子放到皮氏培养皿中,然后放入10只1/2龄期的对苯甲酰脲类具有抗性的小菜蛾(Plutellaxylostella)的幼虫。将培养皿置于25℃的温室中。7天后,检查幼虫的死亡数目,计算百分致死率。重复试验两次,测定平均百分致死率。
结果:
化合物2、11、15、17、20、26、28、30、35、41、45、53、56、62、69、71、81、86、88、90、97、99、102、104、107、127、134、139、142、147、149、152、154、156、159、167和168在200ppm浓度时显示出100%的致死率。
试验实施例4
(抗Cnaphalocrocis medinalis试验)
试验步骤:
将规定浓度的试验化合物溶液散布到3.5叶期的水稻上。溶液经空气干燥后,将处理过的叶子切碎,放到皮氏培养皿中,然后放入10只1/3龄期的rice leafroller(Cnaphalocrocis medinalis)的幼虫。 将培养皿置于25℃的温室中。7天后,检查幼虫的死亡数目,计算百分致死率。重复试验两次,测定平均百分致死率。
结果:
化合物4、9、10、13、24、27、32、42、46、52、55、64、67、70、72、76、82、89、94、95、105、108、110、112、124、128、140、148、151、160、163和165在50ppm浓度时显示出100%的致死率。
试验实施例5
(抗Diabrotica balteata试验)
制剂的制备
载体:7份重量的高岭土
乳化剂:1份重量的去垢剂
为了处理种子,将一定量的活性成分溶于丙酮中,并混合到所述量的、含所述量乳化剂的载体中。
为了涂布种子,将200mg制剂用0.2ml水分散在塑料盆中。向分散液中加入10g玉米,并在旋转振荡器上充分混合2分钟。
试验步骤:
对种子涂层干燥后,将5粒处理过的/未处理过的种谷(seedcernels)加到300ml标准化的湿土中,并保持在20℃。对每种制剂重复制备两次。
两天后,用20只1/2龄期的Diabrotica balteata侵扰各盆,侵扰后7天,观察每盆中出苗植物的数目。
如果所有植物都出苗了,效率计为100% Abbot,如果没有植物出苗,效率则计为0% Abbot。
结果:
化合物8、39、70和95在每10g种谷用0.1g活性成分时显示出100%致死率。
Claims (9)
1.下式化合物:其中R1是卤素;R2是氢或C1-4烷基;R3是氰基、任选地被取代的C1-4烷基、C2-4链烯基或C3-4炔基、C1-4烷基-羰基或C1-4烷氧基-硫代羰基;R4是氢、苯基、苄基、任选地被取代的C1-8烷基、任选地被取代的C2-8链烯基、-COR8、-CO-OR9或
;R5是氢、甲酰基、苯基、任选地被取代的C1-8烷基、任选地被取代的C2-8链烯基、任选地被取代的C3-8炔基、任选地被取代的C1-8烷基-羰基、任选地被取代的C1-6烷基-草酰基、任选地被取代的C1-8烷氧基-羰基、任选地被取代的C1-8烷氧基-草酰基、任选地被取代的C3-8环烷基-羰基、任选地被取代的C2-8链烯基-羰基或任选地被取代的苯甲酰基;R6是氢或卤素;R7是氢、卤素或C1-2烷基;n是0、1或2,条件是当R3是氰基、C1-4烷基-羰基或C1-4烷氧基-硫代羰基时,n是0;是反式或顺式单键;R8是任选地被取代的C1-8烷基、任选地被取代的C2-8链烯基、任选地被取代的苯基、任选地被取代的C3-8环烷基、任选地被取代的C1-8烷基-羰基或任选地被取代的C1-8烷氧基-羰基,或氢;R9是任选地被取代的C1-8烷基、任选地被取代的C3-8环烷基、任选地被取代的C2-8链烯基或任选地被取代的C3-8炔基;R10是氢或C1-4烷基;R11是氢、任选地被取代的C1-4烷基或任选地被取代的苯基;和
Z是氧或硫。
2.制备权利要求1的式(I)化合物的方法,其特征在于:
(a)当R5是氢时,
式中R1、R2、R3、R6、R7和n的定义同前,与式(III)化合物反应,式中R4的定义同前;或者(b)当R5是氢,R4是
,且R11不是氢,则R11由R12代替,R12是任选地被取代的C1-4烷基或任选地被取代的苯基时,
在惰性溶剂存在下,使式(IV)化合物
式中R1、R2、R3、R6、R7和n的定义同前,与式(V)化合物反应,
OCN-R12 (V)
式中R12是任选地被取代的C1-4烷基或任选地被取代的苯基;或者
(c)当R4是-CO-R8或-CO-OR9,条件是R8不是氢,则R8或-OR9由R13代替时,
式中hal是氯或溴,和R13是R8或-OR9;或者
(d)当R5不是氢,则R5由R14代替时,
在惰性溶剂存在下,适当的话在酸结合剂存在下,使式(VII)化合物
式中R1、R2、R3、R4、R6、R7和n的定义同上,与式(VIII)化合物反应,
hal-R14 (VIII)
式中hal和R14的定义同上;或者
(e)当n是1时,
式中R1、R2、R3、R4、R5、R6和R7的定义同上;或者
(f)当n是2时,
式中R1、R2、R3、R4、R5、R6和R7的定义同上,而q是0
或1。
3.权利要求1的化合物,其中:R1是卤素;R2是氢或C1-3烷基;R3是氰基;C1-4烷基,该烷基可被选自卤素、氰基、甲氧基、乙氧基和三甲基甲硅烷基的一个或多个取代基取代;或者是C2-3链烯基、炔丙基、甲基-羰基、甲氧基-硫代羰基或乙氧基-硫代羰基;R4是氢、C1-4烷基、C2-4链烯基、苯基,或是苄基、-CO-R8、-CO-OR9或
;R5是氢;甲酰基;苯基;可被选自卤素、氰基、C1-4烷氧基、C1-4烷硫基、羟基羰基、C1-4烷氧基羰基、苯基、被卤素取代的苯基和甲氧基苯基的一个或多个取代基取代的C1-6烷基;C2-6链烯基;C3-6炔基;C1-6烷基-羰基;C1-6卤代烷基-羰基;C1-4烷氧基-C1-6烷基-羰基;C1-6烷基-草酰基;可被选自C3-6环烷基和C1-4烷氧基的一个或多个取代基取代的C1-6烷氧基-羰基;C1-6烷氧基-草酰基;可被C1-4烷基取代的C3-6环烷基-羰基;可被苯基取代的C2-6链烯基-羰基;或苯甲酰基,它可被选自卤素、硝基、氰基、C1-4烷氧基和C1-4烷硫基的一个或多个取代基取代;R6是氢或卤素;R7是氢或卤素或C1-2烷基;n是0、1或2,条件是当R3是氰基、甲基-羰基、甲氧基-硫代羰基或乙氧基-硫代羰基时,n是0;是反式或顺式单键;R8是可被选自卤素、氰基、C1-4烷氧基、C1-4烷氧基-羰基和苯氧基的一个或多个取代基取代的C1-6烷基;可被选自卤素和苯基的一个或多个取代基取代的C2-6链烯基;可被选自卤素、硝基、氰基、C1-4烷基、C1-4烷氧基和C1-4烷硫基的一个或多个取代基取代的苯基;可被C1-4烷基取代的C3-6环烷基;C1-6烷基-羰基;C1-6烷氧基-羰基;或氢;R9是可被选自卤素、苯基、4-硝基苯基、三甲基甲硅烷基和C3-6环烷基的一个或多个取代基取代的C1-6烷基;C3-6环烷基;可被苯基取代的C2-6链烯基;或C3-6炔基;R10是氢或C1-4烷基;R11是氢;可被卤素取代的C1-4烷基;或可被选自卤素、C1-4烷氧基或C1-4卤代烷氧基的一个或多个取代基取代的苯基;和
Z是氧或硫。
4.权利要求1的化合物,其中:R1是氟、氯、溴或碘;R2是氢、甲基、乙基或正丙基;R3是氰基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、氰基甲基、氟甲基、氯甲基、二氟甲基、三氟甲基、2-氟乙基、2-氯乙基、2,2-二氟乙基、2,2,2-三氟乙基、3-氟丙基、3-氯丙基、2,2,3,3-四氟丙基、甲氧基甲基、乙氧基甲基、三甲基甲硅烷基甲基、乙烯基、烯丙基、炔丙基、甲基-羰基或乙氧基-硫代羰基;R4是氢、甲基、乙基、丙基、异丙基、正丁基、叔丁基、烯丙基、苯基、苄基、-CO-R8、-CO-OR9或
;R5是氢、甲基、乙基、丙基、异丙基、正丁基、叔丁基、正戊基、正 己基、甲氧基甲基、乙氧基甲基、甲硫基甲基、甲硫基乙基、甲氧羰基甲基、乙氧羰基甲基、2-乙氧羰基乙基、二氟甲基、2-氯乙基、2,2-二氟乙基、2,2,2-三氟乙基、氰基甲基、氰基乙基、乙烯基、烯丙基、炔丙基、苯基、苯甲酰基、肉桂酰基、苄基、4-氯苯甲酰基、4-甲氧基苯甲酰基、甲酰基、甲基羰基、乙基羰基、丙基羰基、异丙基羰基、正丁基羰基、2,2,2-三氟乙基羰基、5-溴戊基羰基、甲氧甲基羰基、甲基草酰基、乙基草酰基、丙基草酰基、异丙基草酰基、正丁基草酰基、甲氧羰基、乙氧羰基、丙氧羰基、丁氧羰基、甲氧草酰基、乙氧草酰基、丙氧草酰基、丁氧草酰基、环丙基羰基、1-甲基环丙基羰基、环丙基甲氧基羰基、2-甲氧基乙氧羰基或羟基羰基乙基;R6是氢、氟或氯;R7是氢、溴或甲基;n是0、1或2,条件是当R3是甲基-羰基或乙氧基-硫代羰基时n为0;是反式或顺式单键;R8是甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基、氰基甲基、2-氯乙基、3-氯丙基、4-氯丁基、甲氧甲基、2-甲氧乙基、苯氧甲基、乙氧羰基甲基、乙烯基、异丙烯基、1-丙烯基、2,3,3-三氟-2-丙烯基、苯基、4-氯苯基、4-溴苯基、4-甲基苯基、4-甲氧基苯基、苯乙烯基、环丙基、环戊基、环己基、1-甲基环丙基、甲基羰基、乙基羰基、丙基羰基、甲氧羰基、乙氧羰基、丙氧羰基或氢;R9是甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、新戊基、2-甲基丁基、正己基、三甲基甲硅烷基甲基、烯丙基、环戊基、环己基、2-甲基-2-丙烯基、炔丙基、2-氯乙基、2, 2,2-三氟乙基、2,2,3,3-四氟丙基、环丙基甲基、环己基甲基、苄基或4-硝基苄基;R10是氢或甲基;R11是氢、甲基、乙基、2-氯乙基、苯基、2-氯苯基、2-甲氧基苯基或4-三氟甲氧基苯基;和Z是氧或硫。
5.包含至少一种权利要求1的式(I)化合物的杀虫剂。
6.权利要求1的式(I)化合物用于防治害虫的用途。
7.一种防治害虫的方法,其中让权利要求1的式(I)化合物作用于害虫和/或它们的环境。
8.一种制备杀虫剂的方法,它包括将权利要求1的式(I)化合物与增充剂和/或表面活性剂混合。
9.式(XXIX)的化合物式中
R1为卤素,
R2为氢或C1-4烷基,
R6为氢或卤素,
R7为氢、卤素或C1-2烷基,
n为0、1或2,
X为氰基、任选地被取代的C1-4烷基、C2-4链烯基、C3-4炔基、C1-4烷基-羰基、C1-4烷氧基-硫代羰基或甲脒基及它们的盐,条件是,当X为氰基、C1-4烷基-羰基、C1-4烷氧基-硫代羰基或甲脒基及它们的盐时,n为0。
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JP5074496 | 1996-02-15 |
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EP (1) | EP0742202B1 (zh) |
JP (1) | JPH09278744A (zh) |
KR (1) | KR960041158A (zh) |
CN (1) | CN1143630A (zh) |
AR (1) | AR002738A1 (zh) |
AT (1) | ATE187165T1 (zh) |
AU (1) | AU5208696A (zh) |
BR (1) | BR9602237A (zh) |
CO (1) | CO4650113A1 (zh) |
DE (1) | DE69605353D1 (zh) |
EG (1) | EG20800A (zh) |
MX (1) | MX9601757A (zh) |
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TW (1) | TW323273B (zh) |
Cited By (2)
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CN102126994B (zh) * | 2010-01-19 | 2014-07-09 | 中化蓝天集团有限公司 | 一种二苯酮腙衍生物、其制备方法和用途 |
CN104725288A (zh) * | 2013-12-20 | 2015-06-24 | 兰州大学 | 一种二苯酮腙磺酰脲类化合物及其制备方法和用途 |
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US5679866A (en) * | 1995-01-20 | 1997-10-21 | American Cyanamid Company | Fungicidal methods, compounds and compositions containing benzophenones |
DE69918693T2 (de) | 1998-06-02 | 2005-08-25 | Syngenta Participations Ag | Difluoroalkencarboxanilide und schädlingsbekämpfungsmittel |
TW479053B (en) * | 1998-10-19 | 2002-03-11 | Agro Kanesho Co Ltd | Hydrazineoxoacetamide derivatives and pesticides |
WO2009075080A1 (ja) * | 2007-12-10 | 2009-06-18 | Kumiai Chemical Industry Co., Ltd. | フルオロアルキルスルフィド誘導体及び有害生物防除剤 |
CN103304553B (zh) * | 2013-06-20 | 2015-03-11 | 湖南大学 | 2-(丙烯-2-基)-2,3-二氢-4-苯并呋喃酚及其制备方法与应用 |
US9604316B2 (en) | 2014-09-23 | 2017-03-28 | Globalfoundries Inc. | Tin-based solder composition with low void characteristic |
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NZ189705A (en) * | 1978-03-01 | 1981-07-13 | Boots Co Ltd | Benzophenone-hydrazone derivatives and pesticidal compositions intermediates |
EP0026040B1 (en) * | 1979-08-31 | 1985-03-13 | Fbc Limited | Substituted benzophenone hydrazones, pesticidal compositions containing them and method of combating pests |
AU616041B2 (en) * | 1988-08-26 | 1991-10-17 | Sumitomo Chemical Company, Limited | A hydrazone compound and production therefor, and an insecticidal composition containing the same |
IL105310A0 (en) * | 1992-04-16 | 1993-08-18 | Ciba Geigy Ag | Benzophenone derivatives |
TW268881B (zh) * | 1992-07-07 | 1996-01-21 | Ciba Geigy Ag | |
IN186549B (zh) * | 1995-04-19 | 2001-09-29 | Kumiai Chemical Co Ltd |
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1996
- 1996-05-03 DE DE69605353T patent/DE69605353D1/de not_active Expired - Lifetime
- 1996-05-03 AT AT96106956T patent/ATE187165T1/de not_active IP Right Cessation
- 1996-05-03 EP EP96106956A patent/EP0742202B1/en not_active Expired - Lifetime
- 1996-05-06 AU AU52086/96A patent/AU5208696A/en not_active Abandoned
- 1996-05-08 TR TR96/00373A patent/TR199600373A2/xx unknown
- 1996-05-08 KR KR1019960015136A patent/KR960041158A/ko not_active Application Discontinuation
- 1996-05-09 MX MX9601757A patent/MX9601757A/es not_active Application Discontinuation
- 1996-05-10 TW TW085105516A patent/TW323273B/zh active
- 1996-05-10 AR ARP960102525A patent/AR002738A1/es unknown
- 1996-05-10 CO CO96023681A patent/CO4650113A1/es unknown
- 1996-05-10 US US08/644,139 patent/US6077866A/en not_active Expired - Fee Related
- 1996-05-11 EG EG40496A patent/EG20800A/xx active
- 1996-05-11 CN CN96107424A patent/CN1143630A/zh active Pending
- 1996-05-13 BR BR9602237A patent/BR9602237A/pt not_active Application Discontinuation
- 1996-05-13 JP JP8141187A patent/JPH09278744A/ja active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102126994B (zh) * | 2010-01-19 | 2014-07-09 | 中化蓝天集团有限公司 | 一种二苯酮腙衍生物、其制备方法和用途 |
CN104725288A (zh) * | 2013-12-20 | 2015-06-24 | 兰州大学 | 一种二苯酮腙磺酰脲类化合物及其制备方法和用途 |
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AR002738A1 (es) | 1998-04-29 |
EG20800A (en) | 2000-03-29 |
US6077866A (en) | 2000-06-20 |
DE69605353D1 (de) | 2000-01-05 |
BR9602237A (pt) | 1998-01-13 |
ATE187165T1 (de) | 1999-12-15 |
KR960041158A (ko) | 1996-12-19 |
TW323273B (zh) | 1997-12-21 |
CO4650113A1 (es) | 1998-09-03 |
EP0742202A2 (en) | 1996-11-13 |
EP0742202A3 (en) | 1997-03-19 |
TR199600373A2 (tr) | 1996-12-21 |
EP0742202B1 (en) | 1999-12-01 |
JPH09278744A (ja) | 1997-10-28 |
AU5208696A (en) | 1996-11-21 |
MX9601757A (es) | 1997-07-31 |
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