CN1243002C - 嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物及农业/园艺杀菌剂 - Google Patents
嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物及农业/园艺杀菌剂 Download PDFInfo
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- CN1243002C CN1243002C CNB998154881A CN99815488A CN1243002C CN 1243002 C CN1243002 C CN 1243002C CN B998154881 A CNB998154881 A CN B998154881A CN 99815488 A CN99815488 A CN 99815488A CN 1243002 C CN1243002 C CN 1243002C
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- Prior art keywords
- ome
- alkyl
- alkoxyl group
- oet
- halogen atom
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 4
- 239000003899 bactericide agent Substances 0.000 title claims abstract 3
- WTZRQYJHRXQWTK-UHFFFAOYSA-N 2-pyrimidin-2-yl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C1=NC=CC=N1 WTZRQYJHRXQWTK-UHFFFAOYSA-N 0.000 title abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract description 76
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 54
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 26
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- -1 pyrimidyl benzoglyoxaline Chemical compound 0.000 claims description 78
- 125000003545 alkoxy group Chemical group 0.000 claims description 70
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 45
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 25
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 25
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004306 triazinyl group Chemical group 0.000 claims description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- DHVWECLJLVZKHV-UHFFFAOYSA-N N(C1=CC=CC=C1)C=1N=NNC=2C=1N=CC=2 Chemical class N(C1=CC=CC=C1)C=1N=NNC=2C=1N=CC=2 DHVWECLJLVZKHV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000470 constituent Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 150000008059 anilinopyrimidines Chemical class 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2036
- 125000001309 chloro group Chemical group Cl* 0.000 description 494
- 239000000460 chlorine Substances 0.000 description 203
- 125000001246 bromo group Chemical group Br* 0.000 description 170
- 150000001875 compounds Chemical class 0.000 description 127
- 238000002360 preparation method Methods 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 45
- 239000002904 solvent Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000009835 boiling Methods 0.000 description 31
- 238000000034 method Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000003513 alkali Substances 0.000 description 21
- 238000001035 drying Methods 0.000 description 21
- 238000005406 washing Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000843 powder Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000003810 ethyl acetate extraction Methods 0.000 description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 8
- 238000002386 leaching Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
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- 210000003746 feather Anatomy 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
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- 239000004563 wettable powder Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- ZMBIBKWCKXHEBP-UHFFFAOYSA-N CC1=CC(=C(C=C1)N)NC2=NC(=CC(=C2)OC)OC Chemical class CC1=CC(=C(C=C1)N)NC2=NC(=CC(=C2)OC)OC ZMBIBKWCKXHEBP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003921 pyrrolotriazines Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000228452 Venturia inaequalis Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000005133 alkynyloxy group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
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- 150000003230 pyrimidines Chemical class 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- CFQPVBJOKYSPKG-UHFFFAOYSA-N 1,3-dimethylimidazol-2-one Chemical compound CN1C=CN(C)C1=O CFQPVBJOKYSPKG-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
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- UZLVRGBLDHUIDD-UHFFFAOYSA-N 2-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylbenzene-1,2-diamine Chemical class COC1=NC(OC)=NC(NC=2C(=CC=C(C)C=2)N)=N1 UZLVRGBLDHUIDD-UHFFFAOYSA-N 0.000 description 2
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- NXXQONSDUZQPRJ-UHFFFAOYSA-N 4-chloro-2-n-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzene-1,2-diamine Chemical class COC1=NC(OC)=NC(NC=2C(=CC=C(Cl)C=2)N)=N1 NXXQONSDUZQPRJ-UHFFFAOYSA-N 0.000 description 2
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- 240000008067 Cucumis sativus Species 0.000 description 2
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
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- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
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- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
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- 239000000969 carrier Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
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- 229960003280 cupric chloride Drugs 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical class O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
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- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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- 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 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
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- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
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- CLBDFJIIPMNCSN-UHFFFAOYSA-N n-(4-chloro-2-nitrophenyl)-4,6-dimethoxy-1,3,5-triazin-2-amine Chemical compound COC1=NC(OC)=NC(NC=2C(=CC(Cl)=CC=2)[N+]([O-])=O)=N1 CLBDFJIIPMNCSN-UHFFFAOYSA-N 0.000 description 1
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- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical class CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- 230000002265 prevention Effects 0.000 description 1
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- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
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- 238000010189 synthetic method Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
Abstract
通式[I]所示的嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物、以该衍生物为有效成分的农业/园艺用杀菌剂，及其制备中间体[XV]式中，A为N、CR3；R1和R2相互独立地表示氢原子、卤原子、C1-6烷基、C2-6链烯基等；R3表示氢原子、C1-6烷基、C1-6烷氧基、卤原子；R5表示氨基、硝基等；X表示氢原子，卤原子，硝基，氰基等；Y表示卤原子，硝基，氰基，C1-6烷基等；n表示0或1-3的整数。
Description
技术领域
本发明涉及新颖的嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物及以该衍生物为有效成分的农业/园艺用杀菌剂。
技术背景
作为与本发明的化合物嘧啶基苯并咪唑衍生物有关的化合物有作为医药品记载于美国专利No.5,525,604和欧洲专利No.640,599的4-氨基嘧啶衍生物，作为除草剂记载于国际公开WO94/17059的嘧啶衍生物，但是，无一涉及农业/园艺用杀菌剂。法国专利No.1,476,529中记载了具有杀虫、杀菌活性的苯并咪唑基磺酰胺衍生物，但是，并未公开本发明的化合物。涉及本发明化合物三嗪基苯并咪唑衍生物的化合物，有特开昭47-36837号说明书、特开昭49-17677号说明书和工业化学杂志73卷第5期1000页(1970年)中作为纤维制品的着色剂记载的三嗪衍生物，但是，无一涉及农业/园艺用杀菌剂。而且，关于其制备中间体苯胺基嘧啶衍生物也是未知的。
本发明提供新颖的嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物及以其为有效成分的农业/园艺用杀菌剂。
本发明者为创制新颖的农业/园艺用杀菌剂进行锐意研究的结果，发现本发明的嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物(以下称作本发明化合物)是文献未记载的新颖化合物，而且，作为农业/园艺用杀菌剂显示显著的效果，从而完成了本发明。
发明的揭示
本发明是以通式[I]所示的嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物：
[式中，A表示N、CR3；R1和R2相互独立地表示氢原子，卤原子，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，C1-4卤代烷基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C3-6环烷氧基，C1-4卤代烷氧基，氰基C1-4烷氧基，C1-4烷氧基C1-4烷氧基，C3-6环烷基C1-4烷氧基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基，C1-4烷基羰基，甲酰基，苯基，二-C1-4烷氨基，氰基，C1-6烷基磺酰基；R3表示氢原子，C1-6烷基，C1-6烷氧基，卤原子；X表示氢原子，卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-6烷硫基，C1-6烷基磺酰基、苯氧基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷基羰基，C1-4烷氧基羰基，氨基，—-C1-4烷氨基，二-C1-4烷氨基，苯胺基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基；Y表示卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-4卤代烷氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4烷基羰基，C1-4烷氧基羰基，苯甲酰基，氨基，—-C1-4烷氨基，二-C1-4烷氨基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基；n表示0或1-3的整数。]
以及作为其中间体的式[XV]所示苯胺基嘧啶和苯胺基三嗪衍生物
[式中，A表示N、CR3；R1和R2相互独立地表示氢原子，卤原子，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，C1-4卤代烷基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C3-6环烷氧基，C1-4卤代烷氧基，氰基C1-4烷氧基，C1-4烷氧基C1-4烷氧基，C3-6环烷基C1-4烷氧基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基，C1-4烷基羰基，甲酰基，苯基，二-C1-4烷氨基，氰基，C1-6烷基磺酰基；R3表示氢原子，C1-6烷基，C1-6烷氧基，卤原子；R5表示氨基，硝基，-NHCOX；X表示氢原子，卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-6烷硫基，C1-6烷基磺酰基，苯氧基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷基羰基，C1-4烷氧基羰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，苯胺基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基；Y表示卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-4卤代烷氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4烷基羰基，C1-4烷氧基羰基，苯甲酰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基；n表示0或1-3的整数]
以及含有嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物作为有效成分的农业/园艺用杀菌剂。
关于本说明书中记载的符号和用语说明如下。
卤原子为氟原子、氯原子、溴原子或碘原子。
C1-6等标记表示此处连续的取代基的碳原子数，C1-6则表示1-6个碳原子。
C1-6烷基表示直链或支链烷基，如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、正己基、3，3-二甲基丁基等。
C3-6环烷基可列举如环丙基、环戊基、环己基等。
C1-4卤代烷基表示被卤原子取代的直链或支链烷基，可列举如氟甲基、氯甲基、二氟甲基、二氯甲基、三氟甲基、五氟乙基等。
C2-6链烯基表示直链或支链烯基，可列举如乙烯基、1-丙烯基、2-丙烯基、异丙烯基、1-丁烯基、2-丁烯基等。
C2-6炔基表示直链或支链炔基，可列举如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、4-甲基-1-戊炔基、3-甲基-1-戊炔基等。
C1-6烷氧基表示其烷基部分具有上述定义的烷氧基，可列举如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、异戊氧基、正己氧基等。
C2-6链烯氧基表示其链烯基部分具有上述定义的链烯氧基，可列举如烯丙氧基、异丙烯氧基、2-丁烯氧基等。
C2-6炔氧基表示其炔基部分具有上述定义的炔氧基，可列举如2-丙炔氧基、2-丁炔氧基、3-丁炔氧基等。
C3-6环烷氧基表示其环烷基部分具有上述定义的环烷氧基，可列举如环丙氧基、环戊氧基、环己氧基等。
C1-4卤代烷氧基表示其卤代烷基部分具有上述定义的卤代烷氧基，可列举如氟甲氧基、二氟甲氧基、三氟甲氧基、五氟乙氧基等。
C1-6烷硫基表示其烷基部分具有上述定义的烷硫基，可列举如甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正己硫基等。
C3-6环烷基C1-4烷氧基可列举如环丙基甲氧基、环戊基甲氧基、环己基甲氧基等。
C1-4烷氧基C1-4烷基表示其烷基和烷氧基部分具有上述定义的基团，可列举如甲氧基甲基、乙氧基甲基、异丙氧基甲基、戊氧基甲基、甲氧基乙基、丁氧基乙基等基团。
C1-4烷氧基C1-4烷氧基表示其烷基和烷氧基部分具有上述定义的基团，可列举如甲氧基甲氧基、乙氧基甲氧基、异丙氧基甲氧基、戊氧基甲氧基、甲氧基乙氧基、丁氧基乙氧基等基团。
氰基C1-4烷氧基表示其烷氧基部分具有上述定义的基团，可列举如氰基甲氧基、氰基乙氧基、氰基丙氧基等基团。
C1-4烷基羰基表示其烷基部分具有上述定义的烷基羰基，可列举如乙酰基、丙酰基、丁酰基、异丁酰基、新戊酰基、己酰基等。
C1-4烷氧基羰基表示其烷氧基部分具有上述定义的烷氧基羰基，可列举如甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基、正丁氧基羰基、异丁氧基羰基、仲丁氧基羰基、叔丁氧基羰基、正戊氧基羰基、正己氧基羰基等。
一-C1-4烷氨基表示其烷基部分具有上述定义的-烷氨基，可列举如甲基氨基、乙基氨基、正丙基氨基、异丙基氨基、正丁基氨基、异丁基氨基、仲丁基氨基、叔丁基氨基、正戊基氨基等。
二-C1-4烷氨基，可列举如二甲基氨基、二乙基氨基、二丙基氨基、二丁基氨基等。
C1-6烷基磺酰基表示其烷基部分具有上述定义的烷基磺酰基，可列举如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、正己基磺酰基等。
下面，将通式[I]上述本发明化合物的具体例子记载于表1-表35，但是，本发明化合物并不限于这些化合物。又，化合物编号引用于以后的记载中。
表中的符号分别表示如下意思：Me表示甲基，Et表示乙基，Pr表示正丙基，Pr-i表示异丙基，Bu表示正丁基，Pr-c表示环丙基，Pn-c表示环戊基，Ph表示苯基，Bn表示苄基。例如，Ph(2-Cl)表示2-氯苯基，Bn(4-Cl)表示4-氯苄基。
表1
表2
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-29I-30I-31I-32I-33I-34I-35I-36I-37I-38I-39I-40I-41I-42I-43I-44I-45I-46I-47I-48I-49I-50I-51I-52I-53I-54I-56I-66I-57I-58I-59I-60I-61I-62 | NHMe H CH OMe OMeN(Me)2 H CH OMe OMeNHPh H CH OMe OMeCO2Et H CH OMe OMeCOMe H CH OMe OMePh H CH OMe OMePh(4-Cl) H CH OMe OMePh(4-Me) H CH OMe OMePh(4-OMe) H CH OMe OMeCN H CH OMe OMeNO2 H CH OMe OMeH H N OMe OMeCl H N OMe OMeBr H N OMe OMeSMe H N OMe OMeSO2Me H N OMe OMeMe H N OMe OMeEt H N OMe OMePr H N OMe OMePr-i H N OMe OMePr-c H N OMe OMeBu H N OMe OMeBn H N OMe OMeBn(4-Cl) H N OMe OMeBn(4-Me) H N OMe OMeBn(4-OMe) H N OMe OMeCH＝CH2 H N OMe OMeC≡CH H N OMe OMeOMe H N OMe OMeOCH2CH＝CH2 H N OMe OMeOCH2C≡CH H N OMe OMeOCH2CF3 H N OMe OMeOPh H N OMe OMeCH2OEt H N OMe OMe | 135-1381.56421.6219141-144167-168148-151168-171180-182127-128135-141 |
表3
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-63I-64I-65I-66I-67I-68I-69I-70I-71I-72I-73I-74I-75I-76I-77I-78I-79I-80I-81I-82I-83I-84I-85I-86I-87I-88I-89I-90I-91I-92I-93I-94I-95I-96 | CH2Cl H N OMe OMeCH2I H N OMe OMeCCl3 H N OMe OMeCF3 H N OMe OMeC2F5 H N OMe OMeNH2 H N OMe OMeNHMe H N OMe OMeN(Me)2 H N OMe OMeNHPh H N OMe OMeCO2Et H N OMe OMeCOMe H N OMe OMePh H N OMe OMePh(4-Cl) H N OMe OMePh(4-Me) H N OMe OMePh(4-OMe) H N OMe OMeCN H N OMe OMeNO2 H N OMe OMeH 4-Me CH OMe OMeH 4-Cl CH OMe OMeH 5-F CH OMe OMeH 5-Cl CH OMe OMeH 5-Br CH OMe OMeH 5-Me CH OMe OMeH 5-Bu-t CH OMe OMeH 5-CF3 CH OMe OMeH 5-OMe CH OMe OMeH 5-OEt CH OMe OMeH 5-OPr CH OMe OMeH 5-OCF3 CH OMe OMeH 5-OCH2CH＝CH2 CH OMe OMeH 5-OCH2C≡CH CH OMe OMeH 5-OPh CH OMe OMeH 5-OPh(4-Cl) CH OMe OMeH 5-OPh(4-Me) CH OMe OMe | 143-146261-264138-141175-178181-184181-184168-169138-141173-174162-164169-171138-141 |
表4
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-97I-98I-99I-100I-101I-102I-103I-104I-105I-106I-107I-108I-109I-110I-111I-112I-113I-114I-115I-116I-117I-118I-119I-120I-121I-122I-123I-124I-125I-126I-127I-128I-129I-130 | H 5-OPh(4-OMe) CH OMe OMeH 5-SMe CH OMe OMeH 5-CH2OMe CH OMe OMeH 5-COMe CH OMe OMeH 5-COPh CH OMe OMeH 5-CO2Et CH OMe OMeH 5-Ph CH OMe OMeH 5-Ph(4-Cl) CH OMe OMeH 5-Ph(4-Me) CH OMe OMeH 5-Ph(4-OMe) CH OMe OMeH 5-NO2 CH OMe OMeH 5-NH2 CH OMe OMeH 5-NHMe CH OMe OMeH 5-N(Me)2 CH OMe OMeH 5-CN CH OMe OMeH 6-F CH OMe OMeH 6-Cl CH OMe OMeH 6-Me CH OMe OMeH 6-CF3 CH OMe OMeH 6-OMe CH OMe OMeH 6-CO2Et CH OMe OMeH 6-COPh CH OMe OMeH 7-Me CH OMe OMeH 7-Cl CH OMe OMeH 5，6-Cl2 CH OMe OMeH 5，6-(Me)2 CH OMe OMeH 5，6-(OMe)2 CH OMe OMeH 4-Br，6-CF3 CH OMe OMeH 4-Cl，6-CF3 CH OMe OMeH 4，5，6-F3 CH OMe OMeH 4-Me N OMe OMeH 4-Cl N OMe OMeH 5-F N OMe OMeH 5-Cl N OMe OMe | 223-226185-188162-165249-252192-193199-202134-136192-193184-185184-187176-179134-137217-220185-187188-191204-206175-178 |
表5
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-131I-132I-133I-134I-135I-136I-137I-138I-139I-140I-141I-142I-143I-144I-145I-146I-147I-148I-149I-150I-151I-152I-153I-154I-155I-156I-157I-158I-159I-160I-161I-162I-163I-164 | H 5-Br N OMe OMeH 5-I N OMe OMeH 5-Me N OMe OMeH 5-Et N OMe OMeH 5-Pr N OMe OMeH 5-Pr-i N OMe OMeH 5-Bu-t N OMe OMeH 5-CH＝CH2 N OMe OMeH 5-C≡CBu N OMe OMeH 5-CF3 N OMe OMeH 5-OMe N OMe OMeH 5-OEt N OMe OMeH 5-OPr N OMe OMeH 5-OCF3 N OMe OMeH 5-OCH2CH＝CH2 N OMe OMeH 5-OCH2C≡CH N OMe OMeH 5-OPh N OMe OMeH 5-OPh(4-Cl) N OMe OMeH 5-OPh(4-Me) N OMe OMeH 5-OPh(4-OMe) N OMe OMeH 5-SMe N OMe OMeH 5-CH2OMe N OMe OMeH 5-COMe N OMe OMeH 5-COPh N OMe OMeH 5-CO2Et N OMe OMeH 5-Ph N OMe OMeH 5-Ph(4-Cl) N OMe OMeH 5-Ph(4-Me) N OMe OMeH 5-Ph(4-OMe) N OMe OMeH 5-NO2 N OMe OMeH 5-NH2 N OMe OMeH 5-NHMe N OMe OMeH 5-N(Me)2 N OMe OMeH 5-CN N OMe OMe | ＞300145-148177-180120-123101-10487-90146-147164-167210-213 |
表6
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-165I-166I-167I-168I-169I-170I-171I-172I-173I-174I-175I-176I-177I-178I-179I-180I-181I-182I-183I-184I-185I-186I-187I-188I-189I-190I-191I-192I-193I-194I-195I-196I-197I-198 | H 6-F N OMe OMeH 6-Cl N OMe OMeH 6-Me N OMe OMeH 6-CF3 N OMe OMeH 6-OMe N OMe OMeH 6-NO2 N OMe OMeH 6-CO2Et N OMe OMeH 6-COPh N OMe OMeH 7-Me N OMe OMeH 7-Cl N OMe OMeH 5，6-Cl2 N OMe OMeH 5，6-(Me)2 N OMe OMeH 5，6-(OMe)2 N OMe OMeH 4-Br，6-CF3 N OMe OMeH 4-Cl，6-CF3 N OMe OMeH 4，5，6-F3 N OMe OMeMe 4-Me CH OMe OMeMe 4-Cl CH OMe OMeMe 5-F CH OMe OMeMe 5-Cl CH OMe OMeMe 5-Br CH OMe OMeMe 5-Me CH OMe OMeMe 5-Bu-t CH OMe OMeMe 5-CF3 CH OMe OMeMe 5-OMe CH OMe OMeMe 5-OEt CH OMe OMeMe 5-OPr CH OMe OMeMe 5-OCF3 CH OMe OMeMe 5-OPh CH OMe OMeMe 5-CO2Et CH OMe OMeMe 5-COPh CH OMe OMeMe 5-Ph CH OMe OMeMe 5-NH2 CH OMe OMeMe 5-N(Me)2 CH OMe OMe | ＞300176-179193-196127-130163-165153-156180-183163-166126-129129-132190-193211-214137-139173-176169-171164-166 |
表7
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-199I-200I-201I-202I-203I-204I-205I-206I-207I-208I-209I-210I-211I-212I-213I-214I-215I-216I-217I-218I-219I-220I-221I-222I-223I-224I-225I-226I-227I-228I-229I-230I-231I-232 | Me 5-CN CH OMe OMeMe 6-F CH OMe OMeMe 6-Cl CH OMe OMeMe 6-Me CH OMe OMeMe 6-CF3 CH OMe OMeMe 6-OMe CH OMe OMeMe 6-OEt CH OMe OMeMe 6-OPr CH OMe OMeMe 6-CO2Et CH OMe OMeMe 6-COPh CH OMe OMeMe 5，6-Cl2 CH OMe OMeMe 5，6-(Me)2 CH OMe OMeMe 5，6-(OMe)2 CH OMe OMeMe 4-Me N OMe OMeMe 4-Cl N OMe OMeMe 5-F N OMe OMeMe 5-Cl N OMe OMeMe 5-Br N OMe OMeMe 5-I N OMe OMeMe 5-Me N OMe OMeMe 5-Et N OMe OMeMe 5-Pr N OMe OMeMe 5-Pr-i N OMe OMeMe 5-Bu-t N OMe OMeMe 5-CH＝CH2 N OMe OMeMe 5-C≡CBu N OMe OMeMe 5-CF3 N OMe OMeMe 5-OMe N OMe OMeMe 5-OEt N OMe OMeMe 5-OPr N OMe OMeMe 5-OCF3 N OMe OMeMe 5-OPh N OMe OMeMe 5-SMe N OMe OMeMe 5-CO2Me N OMe OMe | 211-214162-163165-166128-131162-165158-161184-187179-182204-206169-172180-182185-188173-176＞300161-164192-195113-116128-131124-125143-144111-114167-170161-164128-131148-151 |
表8
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-233I-234I-235I-236I-237I-238I-239I-240I-241I-242I-243I-244I-245I-246I-247I-248I-249I-250I-251I-252I-253I-254I-255I-256I-257I-258I-259I-260I-261I-262I-263I-264I-265I-266 | Me 5-CO2Et N OMe OMeMe 5-COMe N OMe OMeMe 5-COPh N OMe OMeMe 5-Ph N OMe OMeMe 5-NH2 N OMe OMeMe 5-N(Me)2 N OMe OMeMe 5-CN N OMe OMeMe 6-F N OMe OMeMe 6-Cl N OMe OMeMe 6-Me N OMe OMeMe 6-CF3 N OMe OMeMe 6-OMe N OMe OMeMe 6-OEt N OMe OMeMe 6-OPr N OMe OMeMe 6-CO2Et N OMe OMeMe 6-COPh N OMe OMeMe 5，6-Cl2 N OMe OMeMe 4，6-(Me)2 N OMe OMeMe 5，6-(Me)2 N OMe OMeMe 5，6-(OMe)2 N OMe OMeCl 4-Me CH OMe OMeCl 4-Cl CH OMe OMeCl 5-F CH OMe OMeCl 5-Cl CH OMe OMeCl 5-Br CH OMe OMeCl 5-Me CH OMe OMeCl 5-CF CH OMe OMeCl 5-OMe CH OMe OMeCl 5-OEt CH OMe OMeCl 5-OPr CH OMe OMeCl 5-OCF3 CH OMe OMeCl 5-OPh CH OMe OMeCl 5-COPh CH OMe OMeCl 5-Ph CH OMe OMe | 155-158163-166188-191130-133172-175165-168139-142159-161145-148136-139148-150187-190102-105 |
表9
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-267I-268I-269I-270I-271I-272I-273I-274I-275I-276I-277I-278I-279I-280I-281I-282I-283I-284I-285I-286I-287I-288I-289I-290I-291I-292I-293I-294I-295I-296I-297I-298I-299I-300 | Cl 5-NH2 CH OMe OMeCl 5-N(Me)2 CH OMe OMeCl 5-CN CH OMe OMeCl 6-F CH OMe OMeCl 6-Cl CH OMe OMeCl 6-Me CH OMe OMeCl 5，6-(OMe)2 CH OMe OMeCl 4-Me N OMe OMeCl 4-Cl N OMe OMeCl 5-F N OMe OMeCl 5-Cl N OMe OMeCl 5-Br N OMe OMeCl 5-Me N OMe OMeCl 5-CF3 N OMe OMeCl 5-OMe N OMe OMeCl 5-OEt N OMe OMeCl 5-OPr N OMe OMeCl 5-OCF3 N OMe OMeCl 5-OPh N OMe OMeCl 5-COPh N OMe OMeCl 5-Ph N OMe OMeCl 5-NH2 N OMe OMeCl 5-N(Me)2 N OMe OMeCl 5-CN N OMe OMeCl 6-F N OMe OMeCl 6-Cl N OMe OMeCl 6-Me N OMe OMeCl 5，6-(OMe)2 N OMe OMeCF3 5-F CH OMe OMeCF3 5-Cl CH OMe OMeCF3 5-Br CH OMe OMeCF3 5-Me CH OMe OMeCF3 5-CF3 CH OMe OMeCF3 5-OMe CH OMe OMe | 163-16498-101146-149159-162133-136114-11693-9678-79129-132 |
表10
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-301I-302I-303I-304I-305I-306I-307I-308I-309I-310I-311I-312I-313I-314I-315I-316I-317I-318I-319I-320I-321I-322I-323I-324I-325I-326I-327I-328I-329I-330I-331I-332I-333I-334 | CF3 5-OEt CH OMe OMeCF3 5-OPr CH OMe OMeCF3 5-N(Me)2 CH OMe OMeCF3 5-CN CH OMe OMeCF3 6-F CH OMe OMeCF3 6-Cl CH OMe OMeCF3 6-Me CH OMe OMeCF3 5，6-(OMe)2 CH OMe OMeCF3 5-F N OMe OMeCF3 5-Cl N OMe OMeCF3 5-Br N OMe OMeCF3 5-Me N OMe OMeCF3 5-Et N OMe OMeCF3 5-Pr N OMe OMeCF3 5-Pr-i N OMe OMeCF3 5-Bu-t N OMe OMeCF3 5-CF3 N OMe OMeCF3 5-OMe N OMe OMeCF3 5-OEt N OMe OMeCF3 5-OPr N OMe OMeCF3 5-OCF3 N OMe OMeCF3 5-SMe N OMe OMeCF3 5-NHMe N OMe OMeCF3 5-N(Me)2 N OMe OMeCF3 5-CN N OMe OMeCF3 5-CO2Me N OMe OMeCF3 5-I N OMe OMeCF3 6-F N OMe OMeCF3 6-Cl N OMe OMeCF3 6-Me N OMe OMeCF3 5，6-(OMe)2 N OMe OMeEt 5-F CH OMe OMeEt 5-Cl CH OMe OMeEt 5-Me CH OMe OMe | 151-154132-135170-173135-138111-114137-140104-10789-92118-121113-116165-168187-190188-191126-129115-118135-138137-140120-122 |
表11
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-335I-336I-337I-338I-339I-340I-341I-342I-343I-344I-345I-346I-347I-348I-349I-350I-351I-352I-353I-354I-355I-356I-357I-358I-359I-360I-361I-362I-363I-364I-365I-366I-367I-368 | Et 5-CF3 CH OMe OMeEt 5-OMe CH OMe OMeEt 5-OEt CH OMe OMeEt 5-OPr CH OMe OMeEt 5-N(Me)2 CH OMe OMeEt 5-CN CH OMe OMeEt 6-F CH OMe OMeEt 6-Cl CH OMe OMeEt 6-Me CH OMe OMeEt 5，6-(OMe)2 CH OMe OMeEt 5-F N OMe OMeEt 5-Cl N OMe OMeEt 5-Me N OMe OMeEt 5-CF3 N OMe OMeEt 5-OMe N OMe OMeEt 5-OEt N OMe OMeEt 5-OPr N OMe OMeEt 5-N(Me)2 N OMe OMeEt 5-CN N OMe OMeEt 6-F N OMe OMeEt 6-Cl N OMe OMeEt 6-Me N OMe OMeEt 5，6-(OMe)2 N OMe OMePr 5-Cl N OMe OMePr-i 5-Cl N OMe OMePr-c 5-Cl N OMe OMeNH2 5-F CH OMe OMeNH2 5-Me CH OMe OMeNH2 5-CF3 CH OMe OMeNH2 5-OMe CH OMe OMeNH2 5-OEt CH OMe OMeNH2 6-Me CH OMe OMeNH2 5，6-(OMe) CH OMe OMeNH2 5-Cl N OMe OMe | 117-118118-120125-128128-131160-163146-149236-239＞300268-271232-235239-242＞300293-296 |
表12
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-369I-370I-371I-372I-373I-374I-375I-376I-377I-378I-379I-380I-381I-382I-383I-384I-385I-386I-387I-388I-389I-390I-391I-392I-393I-394I-395I-396I-397I-398I-399I-400I-401I-402 | NH2 5-Me N OMe OMeNH2 5-CF3 N OMe OMeNH2 5-OMe N OMe OMeNH2 5-OEt N OMe OMeNH2 6-Me N OMe OMeNH2 5，6-(OMe)2 N OMe OMeNHMe 5-Cl N OMe OMeN(Me)2 5-Cl N OMe OMeCH2OMe 5-Cl N OMe OMePh 5-Cl N OMe OMeBn 5-Cl N OMe OMeCN 5-Cl CH OMe OMeCN 5-Me CH OMe OMeCN 5-CF3 CH OMe OMeCN 5-OMe CH OMe OMeCN 5-Cl N OMe OMeCN 5-Me N OMe OMeCN 5-CF3 N OMe OMeCN 5-OMe N OMe OMeSMe 5-Cl CH OMe OMeSMe 5-Me CH OMe OMeSMe 5-CF3C H OMe OMeSMe 5-OMe CH OMe OMeSMe 6-Cl CH OMe OMeSMe 6-Me CH OMe OMeSMe 5-Cl N OMe OMeSMe 5-Me N OMe OMeSMe 5-CF3 N OMe OMeSMe 5-OMe N OMe OMeSMe 6-Cl N OMe OMeSMe 6-Me N OMe OMeCCl3 5-Cl CH OMe OMeCCl3 5-Me CH OMe OMeCCl3 5-OMe CH OMe OMe | 272-275258-24166-69105-108137-140192-195223-226229-231184-187155-158135-138132-134 |
表13
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-403I-404I-405I-406I-407I-408I-409I-410I-411I-412I-413I-414I-415I-416I-417I-418I-419I-420I-421I-422I-423I-424I-425I-426I-427I-428I-429I-430I-431I-432I-433I-434I-435I-436 | CCl3 6-Cl CH OMe OMeCCl3 6-Me CH OMe OMeCCl3 5-Cl N OMe OMeCCl3 5-Me N OMe OMeCCl3 5-OMe N OMe OMeCCl3 5-Br N OMe OMeCCl3 6-Cl N OMe OMeCCl3 6-Me N OMe OMeCF2Cl 5-Me N OMe OMeCF2Cl 5-Cl N OMe OMeCF2Cl 5-Br N OMe OMeCF2Cl 5-OMe N OMe OMeCH2Cl 5-Me N OMe OMeCH2Cl 5-Cl N OMe OMeCH2Cl 5-Br N OMe OMeCH2Cl 5-OMe N OMe OMeC2F5 5-Me N OMe OMeC2F5 5-Cl N OMe OMeC2F5 5-Br N OMe OMeC2F5 5-OMe N OMe OMeSO2Me 5-Cl CH OMe OMeSO2Me 5-Me CH OMe OMeSO2Me 6-Me CH OMe OMeSO2Me 5-Cl N OMe OMeSO2Me 5-Me N OMe OMeSO2Me 6-Me N OMe OMeOMe 5-Cl CH OMe OMeOMe 6-Cl CH OMe OMeOMe 5-CI N OMe OMeOMe 6-Cl N OMe OMeH H N OMe OEtH 5-Cl N OMe OEtH 5-Br N OMe OEtH 5-Me N OMe OEt | 136-139123-126140-151109-11186-89143-145160-161149-152176-177182-185178-180194-196 |
表14
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-437I-438I-439I-440I-441I-442I-443I-444I-445I-446I-447I-448I-449I-450I-451I-452I-453I-454I-455I-456I-457I-458I-459I-460I-461I-462I-463I-464I-465I-466I-467I-468I-469I-470 | Me H N OMe OEtMe 5-Cl N OMe OEtMe 5-Br N OMe OEtMe 5-Me N OMe OEtCl 5-Cl N OMe OEtCl 5-Br N OMe OEtCl 5-Me N OMe OEtCF3 H N OMe OEtCF3 5-Me N OMe OEtCF3 5-Cl N OMe OEtCF3 5-Br N OMe OEtCF2Cl 5-Cl N OMe OEtCF2Cl 5-Br N OMe OEtCF2Cl 5-Me N OMe OEtCH2Cl 5-Cl N OMe OEtCH2Cl 5-Br N OMe OEtCH2Cl 5-Me N OMe OEtC2F5 5-Cl N OMe OEtC2F5 5-Br N OMe OEtC2F5 5-Me N OMe OEtH H CH OEt OEtCl H CH OEt OEtBr H CH OEt OEtSMe H CH OEt OEtMe H CH OEt OEtEt H CH OEt OEtOMe H CH OEt OEtOEt H CH OEt OEtCF3 H CH OEt OEtNH2 H CH OEt OEtCN H CH OEt OEtH H N OEt OEtCl H N OEt OEtBr H N OEt OEt | 153-156143-145155-156147-150149-151138-139122-12479-82122-12588-9190-9387-8996-9990-92222-225153-156 |
表15
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-471I-472I-473I-474I-475I-476I-477I-478I-479I-480I-481I-482I-483I-484I-485I-486I-487I-488I-489I-490I-491I-492I-493I-494I-495I-496I-497I-498I-499I-500I-501I-502I-503I-504 | SMe H N OEt OEtMe H N OEt OEtEt H N OEt OEtOMe H N OEt OEtOEt H N OEt OEtCF3 H N OEt OEtNH2 H N OEt OEtCN H N OEt OEtH 5-F CH OEt OEtH 5-Cl CH OEt OEtH 5-Br CH OEt OEtH 5-Me CH OEt OEtH 5-CF3 CH OEt OEtH 5-OMe CH OEt OEtH 5-OEt CH OEt OEtH 6-Cl CH OEt OEtH 5，6-(OMe)2 CH OEt OEtH 5-F N OEt OEtH 5-Cl N OEt OEtH 5-Br N OEt OEtH 5-Me N OEt OEtH 5-Bu-t N OEt OEtH 5-CF3 N OEt OEtH 5-OMe N OEt OEtH 5-OEt N OEt OEtH 6-Cl N OEt OEtH 5，6-(OMe)2 N OEt OEtMe 5-F CH OEt OEtMe 5-Cl CH OEt OEtMe 5-Br CH OEt OEtMe 5-Me CH OEt OEtMe 5-CF3 CH OEt OEtMe 5-OMe CH OEt OEtMe 5-OEt CH OEt OEt | 156-159177-180135-138165-168164-167170-173107-110131-133171-174119-122131-134141-144 |
表16
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-505I-506I-507I-508I-509I-510I-511I-512I-513I-514I-515I-516I-517I-518I-519I-520I-521I-522I-523I-524I-525I-526I-527I-528I-529I-530I-531I-532I-533I-534I-535I-536I-537I-538 | Me 5-OCF3 CH OEt OEtMe 5-CN CH OEt OEtMe 6-F CH OEt OEtMe 6-Cl CH OEt OEtMe 6-Me CH OEt OEtMe 6-CF3 CH OEt OEtMe 6-OMe CH OEt OEtMe 5，6-(OMe)2 CH OEt OEtMe 5-F N OEt OEtMe 5-Cl N OEt OEtMe 5-Br N OEt OEtMe 5-Me N OEt OEtMe 5-Bu-t N OEt OEtMe 5-CF3 N OEt OEtMe 5-OMe N OEt OEtMe 5-OEt N OEt OEtMe 5-OCF3 N OEt OEtMe 5-CN N OEt OEtMe 6-F N OEt OEtMe 6-Cl N OEt OEtMe 6-Me N OEt OEtMe 6-CF3 N OEt OEtMe 6-OMe N OEt OEtMe 5，6-(OMe)2 N OEt OEtCl 5-Cl CH OEt OEtCl 5-Me CH OEt OEtCl 5-OMe CH OEt OEtCl 5-OEt CH OEt OEtCl 5，6-(OMe)2 CH OEt OEtCl 5-Cl N OEt OEtCI 5-Me N OEt OEtCl 5-OMe N OEt OEtCl 5-OEt N OEt OEtCl 5，6-(OMe)2 N OEt OEt | 133-134146-149138-141135-138175-178169-172141-144107-109101-103153-156130-133 |
表17
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-539I-540I-541I-542I-543I-544I-545I-546I-547I-548I-549I-550I-551I-552I-553I-554I-555I-556I-557I-558I-559I-560I-561I-562I-563I-564I-565I-566I-567I-568I-569I-570I-571I-572 | CF3 5-Me CH OEt OEtCF3 5-OMe CH OEt OEtCF3 5，6-(OMe)2 CH OEt OEtCF3 H N OEt OEtCF3 5-Me N OEt OEtCF3 5-OMe N OEt OEtCF3 5-Cl N OEt OEtCF3 5-Br N OEt OEtEt 5-Me CH OEt OEtEt 5-OMe CH OEt OEtEt 5，6-(OMe)2 CH OEt OEtCCl3 5-Cl N OEt OEtCCl3 5-Br N OEt OEtCCl3 5-Me N OEt OEtCCl3 5-OMe N OEt OEtCF2Cl 5-Cl N OEt OEtCF2Cl 5-Br N OEt OEtCF2Cl 5-Me N OEt OEtCH2Cl 5-Cl N OEt OEtCH2Cl 5-Br N OEt OEtCH2Cl 5-Me N OEt OEtC2F5 5-Cl N OEt OEtC2F5 5-Br N OEt OEtC2F5 5-Me N OEt OEtCN 5-Cl CH OEt OEtCN 5-OMe CH OEt OEtCN 5，6-(OMe)2 CH OEt OEtCN 5-Me N OEt OEtCN 5-OMe N OEt OEtCN 5-Cl N OEt OEtSMe 5-Cl CH OEt OEtSMe 5-Me CH OEt OEtSMe 5-Cl N OEt OEtSMe 5-Me N OEt OEt | 163-165140-143138-141120-123110-113170-172167-169 |
表18
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-573I-574I-575I-576I-577I-578I-539I-580I-581I-582I-583I-584I-585I-586I-587I-588I-589I-590I-591I-592I-593I-594I-595I-596I-597I-598I-599I-600I-601I-602I-603I-604I-605I-606 | SO2Me 5-Cl CH OEt OEtSO2Me 5-Me CH OEt OEtOMe 5-Cl CH OEt OEtH H CH OPr OPrH H N OPr OPrH 5-Cl N OPr OPrH 5-Br N OPr OPrMe 5-C1 N OPr OPrMe 5-Br N OPr OPrMe 5-Me N OPr OPrCF3 5-Cl N OPr OPrCF3 5-Br N OPr OPrCF3 5-Me N OPr OPrH H CH OPr-i OPr-iMe 5-Cl CH OPr-i OPr-iMe 5-Me CH OPr-i OPr-iH H N OPr-i OPr-iH 5-Cl N OPr-i OPr-iH 5-Br N OPr-i OPr-iMe 5-Cl N OPr-i OPr-iMe 5-Br N OPr-i OPr-iMe 5-Me N OPr-i OPr-iCF3 5-Cl N OPr-i OPr-iCF3 5-Br N OPr-i OPr-iCF3 5-Me N OPr-i OPr-iH H N OCH2CH＝CH2 OCH2CH＝CH2H 5-Cl N OCH2CH＝CH2 OCH2CH＝CH3H 5-Br N OCH2CH＝CH2 OCH2CH＝CH2Me 5-Cl N OCH2CH＝CH2 OCH2CH＝CH2Me 5-Br N OCH2CH＝CH2 OCH2CH＝CH2Me 5-Me N OCH2CH＝CH2 OCH2CH＝CH2CF3 5-Cl N OCH2CH＝CH2 OCH2CH＝CH2CF3 5-Br N OCH2CH＝CH2 OCH2CH＝CH2CF3 5-Me N OCH2CH＝CH2 OCH2CH＝CH2 | 167-170143-14689-90128-13171-74115-11785-8897-100158-161 |
表19
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-607I-608I-609I-610I-611I-612I-613I-614I-615I-616I-617I-618I-619I-620I-621I-622I-623I-624I-625I-626I-627I-628I-629I-630I-631I-632I-633I-634I-635I-636I-637I-638I-639I-640 | H H N OCH2C≡CH OCH2C≡CHH 5-Cl N OCH2C≡CH OCH2C≡CHH 5-Br N OCH2C≡CH OCH2C≡CHMe 5-Cl N OCH2C≡CH OCH2C≡CHMe 5-Br N OCH2C≡CH OCH2C≡CHMe 5-Me N OCH2C≡CH OCH2C≡CHCF3 5-Cl N OCH2C≡CH OCH2C≡CHCF3 5-Br N OCH2C≡CH OCH2C≡CHCF3 5-Me N OCH2C≡CH OCH2C≡CHMe 5-Cl CH OCH2CN OCH2CNMe 5-Me CH OCH2CN OCH2CNH 5-Br N OCH2CN OCH2CNMe 5-Cl N OCH2CN OCH2CNMe 5-Br N OCH2CN OCH2CNMe 5-Me N OCH2CN OCH2CNCF3 5-Cl N OCH2CN OCH2CNCF3 5-Br N OCH2CN OCH2CNCF3 5-Me N OCH2CN OCH2CNMe 5-Cl CH OCH2CH2OMe OCH2CH2OMeMe 5-Me CH OCH2CH2OMe OCH2CH2OMeH 5-Br N OCH2CH2OMe OCH2CH2OMeMe 5-Cl N OCH2CH2OMe OCH2CH2OMeMe 5-Br N OCH2CH2OMe OCH2CH2OMeMe 5-Me N OCH2CH2OMe OCH2CH2OMeCF3 5-Cl N OCH2CH2OMe OCH2CH2OMeCF3 5-Br N OCH2CH2OMe OCH2CH2OMeCF3 5-Me N OCH2CH2OMe OCH2CH2OMeH 5-Br N OCH2Pr-c OCH2Pr-cMe 5-Cl N OCH2Pr-c OCH2Pr-cMe 5-Br N OCH2Pr-c OCH2Pr-cMe 5-Me N OCH2Pr-c OCH2Pr-cCF3 5-Cl N OCH2Pr-c OCH2Pr-cCF3 5-Br N OCH2Pr-c OCH2Pr-cCF3 5-Me N OCH2Pr-c OCH2Pr-c |
表20
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-641I-642I-643I-644I-645I-646I-647I-648I-649I-650I-651I-652I-653I-654I-655I-656I-657I-658I-659I-660I-661I-662I-663I-664I-665I-666I-667I-668I-669I-670I-671I-672I-673I-674 | Me 5-Me CH OCH2CH2Cl OCH2CH2ClMe 5-Cl CH OCH2CH2Cl OCH2CH2ClMe 5-Me N OCH2CH2Cl OCH2CH2ClMe 5-Cl N OCH2CH2Cl OCH2CH2ClCF3 5-Me N OCH2CH2Cl OCH2CH2ClCF3 5-Cl N OCH2CH2Cl OCH2CH2ClMe 5-Cl N OCH2CH2F OCH2CH2FMe 5-Me N OCH2CH2F OCH2CH2FCF3 5-Me N OCH2CH2F OCH2CH2FCF3 5-Cl N OCH2CH2F OCH2CH2FMe 5-Cl N OCH2CF3 OCH2CF3Me 5-Me N OCH2CF3 OCH2CF3CF3 5-Me N OCH2CF3 OCH2CF3CF3 5-Cl N OCH2CF3 OCH2CF3H H CH OBn OBnH H N OBn OBnH H N OBn(4-Cl) OBn(4-Cl)H H N OBn(4-Me) OBn(4-Me)H H N OBn(4-OMe) OBn(4-OMe)H H CH OMe OPhH H N OMe OPhH H N OMe OPh(4-Cl)H H N OMe OPh(4-Me)H H N OMe OPh(4-OMe)H H CH OMe OCHF2H H N OMe OCHF2H H CH OMe HMe H CH OMe HH 5-Cl CH OMe HH 5-Me CH OMe HMe 5-Cl CH OMe HMe 5-Me CH OMe HMe 5-CF3 CH OMe HMe 5-OMe CH OMe H | 131-132138-139114-116173-176140-142127-130113-114 |
表21
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-675I-676I-677I-678I-679I-680I-681I-682I-683I-684I-685I-686I-687I-688I-689I-690I-691I-692I-693I-694I-695I-696I-697I-698I-699I-700I-701I-702I-703I-704I-705I-706I-707I-708 | Me 6-Cl CH OMe HMe 5，6-(OMe)2 CH OMe HCl 5-Cl CH OMe HCl 5-Me CH OMe HCl 5-CF3 CH OMe HCl 5-OMe CH OMe HCl 5，6-(OMe)2 CH OMe HCF3 5-Cl CH OMe HCF3 5-Me CH OMe HCF3 5-CF3 CH OMe HCF3 5-OMe CH OMe HEt 5-Cl CH OMe HEt 5-Me CH OMe HEt 5-CF3 CH OMe HEt 5-OMe CH OMe HH H CH OEt HMe H CH OEt HH 5-Cl CH OEt HH 5-Me CH OEt HMe 5-Cl CH OEt HMe 5-Me CH OEt HMe 5-CF3 CH OEt HMe 5-OMe CH OEt HMe 5，6-(OMe)2 CH OEt HMe 6-Cl CH OEt HCl 5-Me CH OEt HCl 5-CF3 CH OEt HCl 5-OMe CH OEt HCl 5，6-(OMe)2 CH OEt HCF3 5-Cl CH OEt HCF3 5-Me CH OEt HCF3 5-OMe CH OEt HEt 5-Cl CH OEt HEt 5-Me CH OEt H | 126-130107-10876-79104-107158-160131-132153-155109-111117-118125-12886-87 |
表22
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-709I-710I-711I-712I-713I-714I-715I-716I-717I-718I-719I-720I-721I-722I-723I-724I-725I-726I-727I-728I-729I-730I-731I-732I-733I-734I-735I-736I-737I-738I-739I-740I-741I-742 | Et 5-CF3 CH OEt HEt 5-OMe CH OEt HH H CH OPr HMe 5-Me CH OPr HMe 5-Cl CH OPr HMe 5-OMe CH OPr HH H CH OCH2CH＝CH2 HMe 5-Me CH OCH2CH＝CH2 HMe 5-Cl CH OCH2CH＝CH2 HMe 5-OMe CH OCH2CH＝CH2 HH H CH OBn HMe 5-Me CH OBn HMe 5-Cl CH OBn HH H CH OPh HH H CH OPh(4-Cl) HH H CH OPh(4-Me) HH H CH OPh(4-OMe) HH H CH OMe MeMe H CH OMe MeH 5-Cl CH OMe MeH 5-Me CH OMe MeH 5-CF3 CH OMe MeMe 5-Cl CH OMe MeMe 5-Me CH OMe MeMe 5-CF3 CH OMe MeMe 5-OMe CH OMe MeMe 6-Cl CH OMe MeMe 5，6-(OMe)2 CH OMe MeCl 5-Cl CH OMe MeCl 5-Me CH OMe MeCl 5-OMe CH OMe MeCl 5，6-(OMe)2 CH OMe MeCF3 5-Cl CH OMe MeCF3 5-Me CH OMe Me | 83-86257-260107-110124-127 |
表23
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-743I-744I-745I-746I-747I-748I-749I-750I-751I-752I-753I-754I-755I-756I-757I-758I-759I-760I-761I-762I-763I-764I-765I-766I-767I-768I-769I-770I-771I-772I-773I-774I-775I-776 | CF3 5-OMe CH OMe MeEt 5-Cl CH OMe MeEt 5-Me CH OMe MeEt 5-OMe CH OMe MeH H N OMe MeH 5-Cl N OMe MeH 5-Me N OMe MeH 5-CF3 N OMe MeMe 5-Cl N OMe MeMe 5-Me N OMe MeMe 5-CF3 N OMe MeMe 5-OMe N OMe MeMe 6-Cl N OMe MeMe 5，6-(OMe)2 N OMe MeCl 5-Cl N OMe MeCl 5-Me N OMe MeCl 5-OMe N OMe MeCl 5，6-(OMe)2 N OMe MeCF3 5-Cl N OMe MeCF3 5-Me N OMe MeCF3 5-OMe N OMe MeEt 5-Cl N OMe MeEt 5-Me N OMe MeEt 5-OMe N OMe MeNH2 5-Me N OMe MeH H CH OEt MeMe H CH OEt MeCF3 H CH OEt MeCl H CH OEt MeH 5-Me CH OEt MeMe 5-F CH OEt MeMe 5-Cl CH OEt MeMe 5-Me CH OEt MeMe 5-CF3 CH OEt Me | 124-127117-120117-120＞30057-6092-9495-96105-108108-110 |
表24
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-777I-778I-779I-780I-781I-782I-783I-784I-785I-786I-787I-788I-789I-790I-791I-792I-793I-794I-795I-796I-797I-798I-799I-800I-801I-802I-803I-804I-805I-806I-807I-808I-809I-810 | Me 5-OMe CH OEt MeMe 5-CN CH OEt MeMe 6-Cl CH OEt MeMe 5，6-(OMe)2 CH OEt MeCl 5-Cl CH OEt MeCl 5-Me CH OEt MeCl 5-CF3 CH OEt MeCl 5-OMe CH OEt MeCl 5，6-(OMe)2 CH OEt MeCF3 5-Cl CH OEt MeCF3 5-Me CH OEt MeCF3 5-OMe CH OEt MeEt 5-Cl CH OEt MeEt 5-Me CH OEt MeEt 5-CF3 CH OEt MeEt 5-OMe CH OEt MeH H N OEt MeH 5-Br N OEt MeMe 5-Cl N OEt MeMe 5-Br N OEt MeMe 5-Me N OEt MeMe 5-CF3 N OEt MeCl 5-Cl N OEt MeCl 5-Me N OEt MeCF3 5-Cl N OEt MeCF3 5-Br N OEt MeCF3 5-Me N OEt MeH H CH OPr MeH 5-OMe CH OPr MeMe H CH OPr MeCF3 H CH OPr MeH 5-Cl CH OPr MeH 5-Me CH OPr MeMe 5-F CH OPr Me | 117-11847-50100-10275-7873-76 |
表 25
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-811I-812I-813I-814I-815I-816I-817I-818I-819I-820I-821I-822I-823I-824I-825I-826I-827I-828I-829I-830I-831I-832I-833I-834I-835I-836I-837I-838I-839I-840I-841I-842I-843I-844 | Me 5-Cl CH OPr MeMe 5-Me CH OPr MeMe 5-OMe CH OPr MeMe 6-Cl CH OPr MeMe 5，6-(OMe)2 CH OPr MeCl 5-Cl CH OPr MeCl 5-Me CH OPr MeCl 5-OMe CH OPr MeCl 5，6-(OMe)2 CH OPr MeCF3 5-Cl CH OPr MeCF3 5-Me CH OPr MeCF3 5-CF CH OPr MeCF3 5-OMe CH OPr MeEt 5-Cl CH OPr MeEt 5-Me CH OPr MeEt 5-OMe CH OPr MeH H N OPr MeH 5-Br N OPr MeMe 5-Cl N OPr MeMe 5-Br N OPr MeMe 5-Me N OPr MeMe 5-CF3 N OPr MeCl 5-Cl N OPr MeCl 5-Me N OPr MeCF3 5-Cl N OPr MeCF3 5-Br N OPr MeCF3 5-Me N OPr MeNH2 5-Me N OPr MeH H CH OPr-i MeMe H CH OPr-i MeCF3 H CH OPr-i MeH 5-Cl CH OPr-i MeH 5-Me CH OPr-i MeMe 5-F CH OPr-i Me | 90-9359-6299-101109-11276-7787-90104-107152-15366-681.5805 |
表26
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-845I-846I-847I-848I-849I-850I-851I-852I-853I-854I-855I-856I-857I-858I-859I-860I-861I-862I-863I-864I-865I-866I-867I-868I-869I-870I-871I-872I-873I-874I-875I-876I-877I-878 | Me 5-Cl CH OPr-i MeMe 5-Me CH OPr-i MeMe 5-OMe CH OPr-i MeMe 6-Cl CH OPr-i MeMe 5，6-(OMe)2 CH OPr-i MeCl 5-Cl CH OPr-i MeCl 5-Me CH OPr-i MeCl 5-CF3 CH OPr-i MeCl 5-OMe CH OPr-i MeCl 5，6-(OMe)2 CH OPr-i MeCF3 5-Cl CH OPr-i MeCF3 5-Me CH OPr-i MeCF3 5-OMe CH OPr-i MeEt 5-Cl CH OPr-i MeEt 5-Me CH OPr-i MeEt 5-OMe CH OPr-i MeH H N OPr-i MeH 5-Br N OPr-i MeMe 5-Cl N OPr-i MeMe 5-Br N OPr-i MeMe 5-Me N OPr-i MeMe 5-CF3 N OPr-i MeCl 5-Cl N OPr-i MeCl 5-Me N OPr-i MeCF3 5-Cl N OPr-i MeCF3 5-Br N OPr-i MeCF3 5-Me N OPr-i MeH H CH OBu MeMe H CH OBu MeMe 5-Cl CH OBu MeMe 5-Me CH OBu MeMe 5-OMe CH OBu MeCl 5-Cl CH OBu MeCl 5-Me CH OBu Me | 1.579573-76 |
表27
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-879I-880I-881I-882I-883I-884I-885I-886I-887I-888I-889I-890I-891I-892I-893I-894I-895I-896I-897I-898I-899I-900I-901I-902I-903I-904I-905I-906I-907I-908I-909I-910I-911I-912 | Cl 5-OMe CH OBu MeCF3 5-Cl CH OBu MeCF3 5-Me CH OBu MeCF3 5-OMe CH OBu MeH H CH OCH2CH＝CH2 MeH 5-Me CH OCH2CH＝CH2 MeMe H CH OCH2CH＝CH2 MeMe 5-Cl CH OCH2CH＝CH2 MeMe 5-Me CH OCH2CH＝CH2 MeMe 5-OMe CH OCH2CH＝CH2 MeCl 5-Cl CH OCH2CH＝CH2 MeCl 5-Me CH OCH2CH＝CH2 MeCF3 5-Cl CH OCH2CH＝CH2 MeCF3 5-Me CH OCH2CH＝CH2 MeCF3 5-OMe CH OCH2CH＝CH2 MeH H CH OCH2C≡CH MeH 5-Me CH OCH2C≡CH MeMe H CH OCH2C≡CH MeMe 5-Cl CH OCH2C≡CH MeMe 5-Me CH OCH2C≡CH MeMe 5-OMe CH OCH2C≡CH MeCl 5-Cl CH OCH2C≡CH MeCl 5-Me CH OCH2C≡CH MeCF3 5-Cl CH OCH2C≡CH MeCF3 5-Me CH OCH2C≡CH MeNH2 5-Me CH OCH2C≡CH MeH H CH OBn MeH H CH OPn-c MeMe H CH OPn-c MeMe 5-Cl CH OPn-c MeMe 5-Cl N OPn-c MeH H CH SMe MeMe H CH SMe MeMe 5-Me CH SMe Me | 55-5884-87145-148183-186147-149147-150113-116225-2281.59651.5941139-142 |
表28
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-913I-914I-915I-9161-917I-918I-919I-920I-921I-9221-923I-924I-925I-926I-927I-928I-929I-9301-931I-932I-933I-934I-935I-936I-937I-938I-939I-940I-941I-942I-943I-944I-945I-946 | Me 5-Cl CH SMe MeH H N SMe MeMe 5-Me N SMe MeMe 5-Cl N SMe MeH H CH OMe EtMe 5-Me CH OMe EtMe 5-Cl CH OMe EtMe 5-CF3 CH OMe EtMe 5-OMe CH OMe EtCl 5-Me CH OMe EtCl 5-Cl CH OMe EtH H CH OEt EtMe 5-Me CH OEt EtMe 5-Cl CH OEt EtMe 5-CF3 CH OEt EtMe 5-OMe CH OEt EtCl 5-Me CH OEt EtCl 5-Cl CH OEt EtH H CH OPr EtMe 5-Me CH OPr EtMe 5-Cl CH OPr EtMe 5-CF3 CH OPr EtMe 5-OMe CH OPr EtCl 5-Me CH OPr EtCl 5-Cl CH OPr EtH H N OMe EtH 5-Br N OMe EtMe 5-Me N OMe EtMe 5-Cl N OMe EtMe 5-Br N OMe EtCl 5-Me N OMe EtCl 5-Cl N OMe EtCF3 5-Me N OMe EtCF3 5-Cl N OMe Et | 134-137125-128134-137134-14186-8979-82 |
表 29
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-947I-948I-949I-950I-951I-952I-953I-954I-955I-956I-957I-958I-959I-960I-961I-962I-963I-964I-965I-966I-967I-968I-969I-970I-971I-972I-973I-974I-975I-976I-977I-978I-979I-980 | CF3 5-Br N OMe EtH H N OEt EtH 5-Br N OEt EtMe 5-Me N OEt EtMe 5-Cl N OEt EtMe 5-Br N OEt EtCl 5-Me N OEt EtCl 5-Cl N OEt EtCF3 5-Me N OEt EtCF3 5-Cl N OEt EtCF3 5-Br N OEt EtH H CH OMe PrMe H CH OMe PrCl H CH OMe PrH 5-Cl CH OMe PrH 5-Me CH OMe PrMe 5-F CH OMe PrMe 5-Cl CH OMe PrMe 5-Me CH OMe PrMe 5-OMe CH OMe PrMe 6-Cl CH OMe PrCl 5-C1 CH OMe PrCl 5-Me CH OMe PrCl 5-OMe CH OMe PrCF3 5-Cl CH OMe PrCF3 5-Me CH OMe PrCF3 5-OMe CH OMe PrH H CH OEt PrH 5-Cl CH OEt PrH 5-Me CH OEt PrMe 5-F CH OEt PrMe 5-Cl CH OEt PrMe 5-Me CH OEt PrMe 5-CF3 CH OEt Pr | 97-10079-8296-9866-6797-100 |
| 78-801.58921.6009116-119113-116105-10768-71 |
表30
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-981I-982I-983I-984I-985I-986I-987I-988I-989I-990I-991I-992I-993I-994I-995I-996I-997I-998I-999I-1OO0I-1001I-1002I-1003I-1004I-1005I-1006I-1007I-1008I-1009I-1010I-1011I-1012I-1013I-1014 | Me 5-OMe CH OEt PrCl 5-Cl CH OEt PrCl 5-Me CH OEt PrCl 5-CF3 CH OEt PrCl 5-OMe CH OEt PrCF3 5-Cl CH OEt PrCF3 5-Me CH OEt PrCF3 5-OMe CH OEt PrH H CH OPr PrMe 5-Me CH OPr PrMe 5-Cl CH OPr PrMe 5-OMe CH OPr PrCl 5-Me CH OPr PrCl 5-Cl CH OPr PrH H N OMe PrH 5-Br N OMe PrMe 5-Cl N OMe PrMe 5-Br N OMe PrMe 5-Me N OMe PrCl 5-Cl N OMe PrCl 5-Me N OMe PrCF3 5-Cl N OMe PrCF3 5-Br N OMe PrCF3 5-Me N OMe PrH H N OEt PrH 5-Br N OEt PrMe 5-Cl N OEt PrMe 5-Br N OEt PrMe 5-Me N OEt PrCl 5-Cl N OEt PrCl 5-Me N OPr PrCF3 5-Cl N OPr PrCF3 5-Br N OPr PrCF3 5-Me N OPr Pr | 112-11592-95 |
表31
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-1015I-1016I-1017I-1018I-1019I-1020I-1021I-1022I-1023I-1024I-1025I-1026I-1027I-1028I-1029I-1030I-1031I-1032I-1033I-1034I-1035I-1036I-1037I-1038I-1039I-1040I-1041I-1042I-1043I-1044I-1045I-1046I-1047I-1048 | H H N OMe Pr-cH 5-Br N OMe Pr-cMe 5-Cl N OMe Pr-cMe 5-Br N OMe Pr-cMe 5-Me N OMe Pr-cCF3 5-Cl N OMe Pr-cCF3 5-Br N OMe Pr-cCF3 5-Me N OMe Pr-cH H N OEt Pr-cH 5-Br N OEt Pr-cMe 5-Cl N OEt Pr-cMe 5-Br N OEt Pr-cMe 5-Me N OEt Pr-cCF3 5-Cl N OEt Pr-cCF3 5-Br N OEt Pr-cCF3 5-Me N OEt Pr-cH H N SMe Pr-cH 5-Br N SMe Pr-cMe 5-Cl N SMe Pr-cMe 5-Br N SMe Pr-cMe 5-Me N SMe Pr-cCF3 5-Cl N SMe Pr-cCF3 5-Br N SMe Pr-cCF3 5-Me N SMe Pr-cMe H CH SMe SMeH 5-Cl N SMe SMeH 5-Br N SMe SMeMe H N SMe SMeMe 5-Cl N SMe SMeMe 5-Br N SMe SMeMe 5-Me N SMe SMeCF3 5-Cl N SMe SMeCF3 5-Br N SMe SMeCF3 5-Me N SMe Me | 154-157116-119121-124167-170101-104119-122116-119137-140130-133124-127131-13382-85105-10879-82129-131176-179186-189144-146106-109 |
表32
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-1049I-1050I-1051I-1052I-1053I-1054I-1055I-1056I-1057I-1058I-1059I-1060I-1061I-1062I-1063I-1064I-1065I-1066I-1067I-1068I-1069I-1070I-1071I-1072I-1073I-1074I-1075I-1076I-1077I-1078I-1079I-1080I-1081I-1082 | H 5-Br N OMe SMeMe 5-Cl N OMe SMeMe 5-Br N OMe SMeMe 5-Me N OMe SMeCF3 5-Cl N OMe SMeCF3 5-Br N OMe SMeCF3 5-Me N OMe SMeH H CH OMe PhH H N OMe PhMe 5-Me N OMe PhCF3 6-Me N OMe PhH H CH Cl PhH H N Cl PhH H CH Cl ClMe H CH Cl ClMe 5，6-Cl2 CH Cl ClH H N Cl ClMe H N Cl ClH H CH Cl MeMe H CH Cl MeH H CH Cl N(Me)2H H N Cl N(Me)2Me 5-Cl N N(Me)2 N(Me)2H H CH OMe N(Me)2H H CBr OMe OMeH H CMe OMe OMeH H CMe Cl ClH H COMe H HMe 5-Me COMe H HMe 5-Cl COMe H HH H CH Me MeMe 5-Cl CH Me MeMe 5-CF3 CH Me MeH H CH Me CF3 | 160-162165-168150-153176-179165-168170-172202-205＞300187-190122-125205-208203-206129-132＞300152-155184-187131-134131-132138-140107-110 |
表33
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-1083I-1084I-1085I-1086I-1087I-1088I-1089I-1090I-1091I-1092I-1093I-1094I-1095I-1096I-1097I-1098I-1099I-1100I-1101I-1102I-1103I-1104I-1105I-1106I-1107I-1108I-1109I-1110I-1111I-1112I-1113I-1114I-1115I-1116 | Me 5-Cl CH Me CF3Me 5-Cl N Me CF3H H CH Me EtH 5-Me CH Me EtMe 5-Me CH Me EtMe 5-Cl CH Me EtMe 5-OMe CH Me EtMe 6-Cl CH Me EtCl 5-Cl CH Me EtCl 5-Me CH Me EtH H CH Et EtH 5-Me CH Et EtMe 5-Me CH Et EtMe 5-Cl CH Et EtMe 5-OMe CH Et EtMe 6-Cl CH Et EtCl 5-Cl CH Et EtCl 5-Me CH Et EtH H CH Me Pr-cH 5-Me CH Me Pr-cMe 5-Me CH Me Pr-cMe 5-Cl CH Me Pr-cMe 5-OMe CH Me Pr-cMe 6-Cl CH Me Pr-cCl 5-Cl CH Me Pr-cCl 5-Me CH Me Pr-cH H CH Et Pr-cMe 5-Me CH Et Pr-cMe 5-Cl CH Et Pr-cMe 5-OMe CH Et Pr-cMe 6-Cl CH Et Pr-cCl 5-Cl CH Et Pr-cCl 5-Me CH Et Pr-cH H CH Et Et | 60-6355-58109-11276-7984-8758-6168-7176-7978-8080-83124-125153-156119-122110-113 |
表34
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-1117I-1118I-1119I-1120I-1121I-1122I-1123I-1124I-1125I-1126I-1127I-1128I-1129I-1130I-1131I-1132I-1133I-1134I-1135I-1136I-1137I-1138I-1139I-1140I-1141I-1142I-1143I-1144I-1145I-1146I-1147I-1148I-1149I-1150 | Me 5-Me CH Et EtMe 5-Cl CH Et EtMe 5-OMe CH Et EtMe 6-Cl CH Et EtCl 5-Cl CH Et EtCl 5-Me CH Et EtH H CH C≡CMe MeMe 5-Me CH C≡CMe MeMe 5-Cl CH C≡CMe MeMe 5-Me N C≡CMe MeMe 5-Cl N C≡CMe MeCl 5-Cl CH C≡CMe MeCl 5-Me CH C≡CMe MeH H CH CH＝CH2 MeMe 5-Me CH CH＝CH2 MeMe 5-Cl CH CH＝CH2 MeMe 5-Me N CH＝CH2 MeCl 5-Cl CH CH＝CH2 MeCl 5-Me CH CH＝CH2 MeH H CH CHO MeMe 5-Cl CH CHO MeMe 5-Cl N CHO MeH H CH COMe MeMe 5-Cl CH COMe MeMe 5-Cl N COMe MeH H CH CH2OMe MeMe 5-Cl CH CH2OMe MeMe 5-Me CH CH2OMe MeH H N CH2OMe OMeMe H CH CN CNMe H CH CN MeMe H N CN CNMe H N CN MeMe H CH SO2Me SO2Me | 134-136187-189 |
表35
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| I-1151I-1152 | Me H N SO2Me SO2MeMe H CH SO2Me Me | 183-186 |
本发明化合物通式[I]所述嘧啶基苯并咪唑和三嗪基苯并咪唑衍生物的代表性制备方法举例如下。
<制备方法1>
(式中，X、Y、R1、R2、A和n分别表示与前述相同的意义，L表示卤原子、C1-6烷基磺酰基、苄基磺酰基等离去基团。)
在碱的存在下，将通式[II]所示苯并咪唑衍生物与通式[III]所示嘧啶衍生物、三嗪衍生物在溶剂中反应，可制得通式[I]所示本发明化合物。此处的碱，可使用例如碱金属或碱土金属，特别是钠、钾及镁、钙的碳酸盐、碳酸氢盐、乙酸盐、醇化物、氢氧化物、氢化物或氧化物等。可用于本反应的溶剂只要是不阻碍本反应进行的即可，例如，可使用***、异丙醚、四氢呋喃、二噁烷、一甘醇二甲醚、二甘醇二甲醚等醚类，二氯乙烷、氯仿、四氯化碳、四氯乙烷等卤代烃类，苯、氯苯、硝基苯、甲苯等芳烃类，N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、1，3-二甲基-2-咪唑啉酮、二甲亚砜等。这些惰性溶剂可单独或混合使用。反应温度可选自-20℃至所用惰性溶剂的沸点的范围，较佳为在O℃～80℃的范围内进行。反应时间根据反应温度、反应量，并无限定，但是，一般可选自1小时～48小时的范围。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
通式[II]所示苯并咪唑衍生物有市售，或可用如下公知的方法制备[如Angewandte Chemie，第85卷，第866页(1973年)；Journal of the AmericanChemical Society，第69卷，第2459页(1947年)；Journal of the AmericanChemical Society，第82卷，第3138页(1960年)；Organic Syntheses，第2卷，第65页(1943年)；Organic Syntheses，第4卷，第569页(1963年)记载的方法]。
<制备方法2>
(式中，X、Y、R1、R2、A和n分别表示与前述相同的意义。)
在惰性溶剂中，将通式[IV]所示苯胺基嘧啶衍生物、苯胺基三嗪衍生物与酰化剂反应，可制得通式[V]所示N-酰苯胺衍生物。反应以在碱存在下进行为佳。酰化剂可列举乙酰氯、丙酰氯、苯甲酰氯等酰卤化合物，或三氟乙酸酐、丙酸酐、苯甲酸酐等酸酐。本发明中可使用的惰性溶剂只要不阻碍本反应进行的即可，例如丙酮、甲基乙基酮、环己酮等酮类，***、异丙醚、四氢呋喃、二噁烷、一甘醇二甲醚、二甘醇二甲醚等醚类，乙酸乙酯、乙酸甲酯等酯类，二氯乙烷、氯仿、四氯化碳、四氯乙烷等卤代烃类，苯、氯苯、硝基苯、甲苯等芳烃类，乙腈等腈类，N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、1，3-二甲基-2-咪唑啉酮、二甲亚砜、吡啶、水等。这些惰性溶剂可单独或混合使用。本反应中所用的碱，可使用无机碱或有机碱，例如，作为无机碱，可使用碳酸钠、碳酸钾、碳酸钙、碳酸氢钠、氢氧化钠、氢氧化钾、氢氧化钙等碱金属类或碱土金属类碳酸盐或氢氧化物，氢化锂、氢化钠等碱金属氢化物；作为有机碱，可使用三乙胺、二异丙基乙基胺、吡啶等。反应温度可选自-20℃至所用惰性溶剂的沸点范围，较佳为在0℃～50℃的范围内进行。反应时间并无限制，根据反应温度、反应量等而定，但一般可选自数分钟～48小时的范围。
然后，将通式[V]所示N-酰苯胺衍生物在无溶剂或在溶剂中、根据需要在催化剂存在下，通过环化反应可制得通式[I]所示本发明化合物。此处所用的催化剂，可使用硫酸、盐酸等无机酸，对甲苯磺酸等有机酸。本反应中所用的溶剂，可使用制备方法1中例示的溶剂。反应温度可选自0℃～溶剂沸点的范围，较佳为室温～溶剂沸点的范围。反应时间并无限制，根据反应温度、反应量等而定，但一般可选自1小时～48小时的范围。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
<制备方法3>
(式中，X、Y、R1、R2、A和n分别表示与前述相同的意义。)
将通式[IV]所示苯胺基嘧啶衍生物、苯胺基三嗪衍生物在通式[VI]所示羧酸中，根据需要在酸酐存在下进行加热，可直接制得通式[I]所示本发明化合物。反应温度可选自0℃～所用羧酸的沸点的范围，较佳可在室温～羧酸的沸点的范围内进行。反应时间一般可选自1小时～48小时的范围。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
<制备方法4>
(式中，Y、R1、R2、A和n分别表示与前述相同的意义。)
用文献公知的方法[例如，Journal of the American Chemical Society，第69卷，第2459页(1947年)；Angewandte Chemie，第85卷，第866页(1973年)等记载的方法]，将通式[IV]所示苯胺基嘧啶衍生物、苯胺基三嗪衍生物与通式[VII]所示试剂中的BrCN、H2NCN等在溶剂中进行反应，可制得通式[I-a]所示化合物。本反应中所用的溶剂，可使用制备方法1中例示的溶剂。反应温度可选自-20℃～所用反应混合物的沸点的范围，较佳可在0℃～反应混合物的沸点的范围内进行。反应时间并无限制，根据反应温度、反应量等一般可选自1小时～48小时的范围。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
<制备方法5>
(式中，X’为卤原子，Y、R1、R2、A和n分别表示与前述相同的意义。)
将通式[I-a]所示2-氨基苯并咪唑衍生物按公知的方法[如Sandmeyer法、Schwechten法、Gattermann法等]在常用的溶剂和反应温度下进行重氮化反应，可制得通式[I-d]所示化合物。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
<制备方法6>
(式中，Y、R1、R2、A和n分别表示与前述相同的意义，R4表示C1-6烷基。)
将通式[I-b]所示嘧啶基苯并咪唑衍生物、三嗪基苯并咪唑衍生物按公知的方法氧化，可制得通式[I-e]所示化合物。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。可用于本反应的氧化剂为例如过氧化氢或间氯过苯甲酸等有机过酸等。可使用的溶剂有制备方法1中例示的溶剂。反应温度可选自-20℃～所用反应混合物的沸点的范围，较佳可在5℃～反应混合物的沸点的范围内进行。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
<制备方法7>
(式中，Y、R1、R2、A、L和n分别表示与前述相同的意义，X″表示C1-6烷氧基、C2-6链烯氧基、C2-6炔氧基、C1-6烷硫基或C1-6烷氨基。)
将通式[I-c]所示嘧啶基苯并咪唑衍生物、三嗪基苯并咪唑衍生物与通式[XVI]所示醇、硫醇、胺等在碱存在下、在无溶剂或溶剂中进行反应，可制得通式[I-f]所示本发明化合物。用于本反应的碱和溶剂，可使用制备方法1中例示的碱和溶剂。反应温度可选自-20℃～所用反应混合物的沸点的范围，较佳可在室温～反应混合物的沸点的范围内进行。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
<制备方法8>
(式中，X、Y、A、L和n分别表示与前述相同的意义，Z表示C1-6烷氧基、C2-6链烯氧基、C2-6炔氧基、C1-6烷硫基或二-C1-6烷氨基。)
将通式[I-g]所示嘧啶基苯并咪唑衍生物、三嗪基苯并咪唑衍生物与通式[VIII]所示醇、硫醇、胺等在碱存在下、在无溶剂或适当的溶剂中进行反应，可制得通式[I-h]所示本发明化合物。用于本反应的碱和溶剂，可使用制备方法1中例示的碱和溶剂。反应温度可选自-20℃～所用反应混合物的沸点的范围，较佳可在室温～反应混合物的沸点的范围内进行。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
<制备方法9>
(式中，Y、R1、R2、A和n分别表示与前述相同的意义。)
将通式[IX]所示苯胺基三嗪衍生物在乙酸中或在乙酸酐、乙酸的混合溶剂中用铁粉还原，可制得通式[I-i]所示本发明化合物。反应温度可选自-20℃～所用反应混合物的沸点的范围，较佳可在室温～反应混合物的沸点的范围内进行。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
下面对本发明化合物的制备中间体的合成方法作详细说明。
<制备方法10>
(式中，Y、R1、R2、A、L和n分别表示与前述相同的意义。)
将通式[X]所示N-甲酰苯胺衍生物与通式[III]所示嘧啶衍生物、三嗪衍生物在碱存在下、在惰性溶剂中于-20℃～溶剂沸点范围(较佳为室温至80℃)的反应温度下进行反应。然后，用公知的方法，用盐酸、溴化氢、硫酸等酸或氢氧化钠、氢氧化钾等碱金属氢氧化物进行水解，可制得通式[XI]所示化合物。再将所得的[XI]用铁、氯化锡或伴其他催化剂的氢原子(如钯炭、阮内镍等还原剂)以公知的方法进行还原，可制得通式[IV]所示苯胺基嘧啶衍生物、苯胺基三嗪衍生物。
<制备方法11>通式[XI-b]所示制备中间体的合成
化合物[XI-b]例如可按如下方法合成，但方法不限于此。
(式中，Y、Z和n分别表示与前述相同的意义。)
将通式[XII]所示硝基苯胺衍生物和[XIII]所示氰脲酰氯在碱存在下、在无溶剂或适当的溶剂中进行反应，制得通式[XI-a]所示苯胺基三嗪衍生物，然后，与通式[VIII]所示醇、硫醇、胺等在碱存在下、在无溶剂或适当的溶剂中进行反应，可制得通式[XI-b]所示苯胺基三嗪衍生物。可用于本反应的碱和溶剂，可使用制备方法1中例示的碱和溶剂。反应温度可选自-20℃～所用反应混合物的沸点的范围，较佳可在室温～反应混合物的沸点的范围内进行。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
<制备方法12>通式[XI-c]、[XI-d]所示制备中间体的合成
化合物[XI-c]、[XI-d]例如可按如下方法合成，但方法不限于此。
(式中，R1、Y、L、Z和n分别表示与前述相同的意义。)
将通式[X]所示N-甲酰苯胺衍生物和[XIV]所示三嗪衍生物在碱存在下、在无溶剂或适当的溶剂中进行反应，然后，用公知的方法，用盐酸、溴化氢、硫酸等酸或氢氧化钠、氢氧化钾等碱金属氢氧化物等进行水解，可制得通式[XI-c]所示苯胺基三嗪衍生物。再与通式[VIII]所示醇、硫醇、胺等在碱存在下、在无溶剂或适当的溶剂中进行反应，可制得通式[XI-d]所示苯胺基三嗪衍生物。可用于本反应的碱和溶剂，可使用制备方法1中例示的碱和溶剂。反应温度可选自-20℃～所用反应混合物的沸点的范围，较佳可在室温～反应混合物的沸点的范围内进行。反应结束后，用常规方法从反应***分离目的物，根据需要，用色谱法、重结晶等提纯。
另外，通式[IV]、[V]和[XI]所示苯胺基嘧啶及苯胺基三嗪衍生物也是新化合物，其具体例子记载于下面的表36-65。
表36
表37
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-271-281-291-301-311-321-331-341-351-361-371-381-391-401-411-421-431-441-451-461-471-481-491-501-511-521-531-541-551-561-571-581-59 | Et H N OMe OMePr H N OMe OMePr-i H N OMe OMePr-c H N OMe OMeBu H N OMe OMeBn H N OMe OMeBn(4-Cl) H N OMe OMeBn(4-Me) H N OMe OMeBn(4-OMe) H N OMe OMeCH＝CH2 H N OMe OMeC≡CH H N OMe OMeCH2OEt H N OMe OMeCH2Cl H N OMe OMeCH2I H N OMe OMeCCl3 H N OMe OMeCF3 H N OMe OMeC2F5 H N OMe OMePh H N OMe OMePh(4-Cl) H N OMe OMePh(4-Me) H N OMe OMePh(OMe) H N OMe OMeH 6-Me CH OMe OMeH 6-Cl CH OMe OMeH 5-F CH OMe OMeH 5-Cl CH OMe OMeH 5-Br CH OMe OMeH 5-Me CH OMe OMeH 5-Bu-t CH OMe OMeH 5-CF3 CH OMe OMeH 5-OMe CH OMe OMeH 5-OEt CH OMe OMeH 5-OPr CH OMe OMeH 5-OCF3 CH OMe OMe |
表38
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-601-611-621-631-641-651-661-671-681-691-701-711-721-731-741-751-761-771-781-791-801-811-821-831-841-851-861-871-881-891-901-911-92 | H 5-OCH2CH＝CH2 CH OMe OMeH 5-OCH2C≡CH CH OMe OMeH 5-OPh CH OMe OMeH 5-OPh(4-Cl) CH OMe OMeH 5-OPh(4-Me) CH OMe OMeH 5-OPh(4-OMe) CH OMe OMeH 5-SMe CH OMe OMeH 5-CH2OMe CH OMe OMeH 5-COMe CH OMe OMeH 5-COPh CH OMe OMeH 5-CO2Et CH OMe OMeH 5-Ph CH OMe OMeH 5-Ph(4-Cl) CH OMe OMeH 5-Ph(4-Me) CH OMe OMeH 5-Ph(4-OMe) CH OMe OMeH 5-NO2 CH OMe OMeH 5-NH2 CH OMe OMeH 5-NHMe CH OMe OMeH 5-NMe2 CH OMe OMeH 5-CN CH OMe OMeH 4-F CH OMe OMeH 4-Cl CH OMe OMeH 4-Me CH OMe OMeH 4-CF3 CH OMe OMeH 4-OMe CH OMe OMeH 4-CO2Et CH OMe OMeH 4-COPh CH OMe OMeH 3-Me CH OMe OMeH 3-Cl CH OMe OMeH 4，5-Cl2 CH OMe OMeH 4，5-Me2 CH OMe OMeH 4，5-(OMe)2 CH OMe OMeH 4-CF3，6-Br CH OMe OMe |
表39
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-931-941-951-961-971-981-991-1001-1011-1021-1031-1041-1051-1061-1071-1081-1091-1101-1111-1121-1131-1141-1151-1161-1171-1181-1191-1201-1211-1221-1231-1241-125 | H 4-CF3，6-Cl CH OMe OMeH 4，5，6-F3 CH OMe OMeH 6-Me N OMe OMeH 6-Cl N OMe OMeH 5-F N OMe OMeH 5-Cl N OMe OMeH 5-Br N OMe OMeH 5-Me N OMe OMeH 5-CF3 N OMe OMeH 5-OMe N OMe OMeH 5-OEt N OMe OMeH 5-OPr N OMe OMeH 5-OCF3 N OMe OMeH 5-OCH2CH＝CH2 N OMe OMeH 5-OCH2C≡CH N OMe OMeH 5-OPh N OMe OMeH 5-SMe N OMe OMeH 5-COPh N OMe OMeH 5-CO2Et N OMe OMeH 5-Ph N OMe OMeH 5-Ph(4-Cl) N OMe OMeH 5-Ph(4-Me) N OMe OMeH 5-Ph(4-OMe) N OMe OMeH 5-NO2 N OMe OMeH 5-NH2 N OMe OMeH 5-NHMe N OMe OMeH 5-NMe2 N OMe OMeH 5-CN N OMe OMeH 4-F N OMe OMeH 4-Cl N OMe OMeH 4-Me N OMe OMeH 4-CF3 N OMe OMeH 4-OMe N OMe OMe |
表40
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-1261-1271-1281-1291-1301-1311-1321-1331-1341-1351-1361-1371-1381-1391-1401-1411-1421-1431-1441-1451-1461-1471-1481-1491-1501-1511-1521-1531-1541-1551-1561-1571-158 | H 4-NO2 N OMe OMeH 4-CO2Et N OMe OMeH 4-COPh N OMe OMeH 3-Me N OMe OMeH 3-Cl N OMe OMeH 4，5-C12 N OMe OMeH 4，5-Me2 N OMe OMeH 4，5-(OMe)2 N OMe OMeH 4-CF3，6-Br N OMe OMeH 4-CF3，6-Cl N OMe OMeH 4，5，6-F3 N OMe OMeMe 6-Me CH OMe OMeMe 6-Cl CH OMe OMeMe 6-F CH OMe OMeMe 5-Cl CH OMe OMeMe 5-Br CH OMe OMeMe 5-Me CH OMe OMeMe 5-Bu-t CH OMe OMeMe 5-CF3 CH OMe OMeMe 5-OMe CH OMe OMeMe 5-COPh CH OMe OMeMe 5-Ph CH OMe OMeMe 5-NH2 CH OMe OMeMe 5-NMe2 CH OMe OMeMe 5-CN CH OMe OMeMe 4-F CH OMe OMeMe 4-Cl CH OMe OMeMe 4-Me CH OMe OMeMe 4-CF3 CH OMe OMeMe 4-OMe CH OMe OMeMe 4-COPh CH OMe OMeMe 4，5-Cl2 CH OMe OMeMe 4，5-Me2 CH OMe OMe |
表41
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-1591-1601-1611-1621-1631-1641-1651-1661-1671-1681-1691-1701-1711-1721-1731-1741-1751-1761-1771-1781-1791-1801-1811-1821-1831-1841-1851-1861-1871-1881-1891-1901-191 | Me 4，5-(OMe)2 CH OMe OMeMe 6-Me N OMe OMeMe 6-Cl N OMe OMeMe 5-F N OMe OMeMe 5-Cl N OMe OMeMe 5-Br N OMe OMeMe 5-Me N OMe OMeMe 5-Et N OMe OMeMe 5-Pr N OMe OMeMe 5-Pr-i N OMe OMeMe 5-Bu-t N OMe OMeMe 5-CH＝CH2 N OMe OMeMe 5-C≡CBu N OMe OMeMe 5-CF3 N OMe OMeMe 5-OMe N OMe OMeMe 5-SMe N OMe OMeMe 5-COPh N OMe OMeMe 5-Ph N OMe OMeMe 5-NH2 N OMe OMeMe 5-NMe2 N OMe OMeMe 5-CN N OMe OMeMe 4-F N OMe OMeMe 4-Cl N OMe OMeMe 4-Me N OMe OMeMe 4-CF3 N OMe OMeMe 4-OMe N OMe OMeMe 4-OEt N OMe OMeMe 4-OPr N OMe OMeMe 4-CO2Et N OMe OMeMe 4-COPh N OMe OMeMe 4，5-Cl2 N OMe OMeMe 4，6-Me2 N OMe OMeMe 4，5-Me2 N OMe OMe | 180-183 |
表42
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-1921-1931-1941-1951-1961-1971-1981-1991-2001-2011-2021-2031-2041-2051-2061-2071-2081-2091-2101-2111-2121-2131-2141-2151-2161-2171-2181-2191-2201-2211-2221-2231-224 | Me 4，5-(OMe)2 N OMe OMeCF3 5-F CH OMe OMeCF3 5-Cl CH OMe OMeCF3 5-Br CH OMe OMeCF3 5-Me CH OMe OMeCF3 5-CF3 CH OMe OMeCF3 5-OMe CH OMe OMeCF3 5-OEt CH OMe OMeCF3 5-OPr CH OMe OMeCF3 5-NMe2 CH OMe OMeCF3 5-CN CH OMe OMeCF3 4-F CH OMe OMeCF3 4-Cl CH OMe OMeCF3 4-Me CH OMe OMeCF3 4，5-(OMe)2 CH OMe OMeCF3 5-F N OMe OMeCF3 5-Cl N OMe OMeCF3 5-Br N OMe OMeCF3 5-Me N OMe OMeCF3 5-Et N OMe OMeCF3 5-Pr N OMe OMeCF3 5-Pr-i N OMe OMeCF3 5-Bu-t N OMe OMeCF3 5-CF3 N OMe OMeCF3 5-OMe N OMe OMeCF3 5-OEt N OMe OMeCF3 5-OPr N OMe OMeCF3 5-OCF3 N OMe OMeCF3 5-SMe N OMe OMeCF3 5-NHMe N OMe OMeCF3 5-NMe2 N OMe OMeCF3 5-CN N OMe OMeCF3 5-CO2Me N OMe OMe | 158-160150-151144-147168-171122-125202-205195-198182-185141-144193-196215-218183-185188-191186-189 |
表43
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-2251-2261-2271-2281-2291-2301-2311-2321-2331-2341-2351-2361-2371-2381-2391-2401-2411-2421-2431-2441-2451-2461-2471-2481-2491-2501-2511-2521-2531-2541-2551-2561-257 | CF3 5-I N OMe OMeCF3 4-F N OMe OMeCF3 4-Cl N OMe OMeCF3 6-Me N OMe OMeCF3 4，5-(OMe)2 N OMe OMeEt 5-F CH OMe OMeEt 5-Cl CH OMe OMeEt 5-Me CH OMe OMeEt 5-CF3 CH OMe OMeEt 5-OMe CH OMe OMeEt 5-CN CH OMe OMeEt 4-F CH OMe OMeEt 4-Cl CH OMe OMeEt 4-Me CH OMe OMeEt 4，5-(OMe)2 CH OMe OMeEt 5-F N OMe OMeEt 5-Cl N OMe OMeEt 5-Me N OMe OMeEt 5-CF3 N OMe OMeEt 5-OMe N OMe OMeEt 5-CN N OMe OMeEt 4-F N OMe OMeEt 4-Cl N OMe OMeEt 4-Me N OMe OMeEt 4，5-(OMe)2 N OMe OMePr 5-Cl N OMe OMePr-i 5-Cl N OMe OMePr-c 5-Cl N OMe OMeCH2OMe 5-Cl N OMe OMePh 5-Cl N OMe OMePh 5-Br N OMe OMePh(4-Cl) 5-Cl N OMe OMePh(4-Me) 5-Cl N OMe OMe | 169-172137-140149-152181-184176-179 |
表44
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-2581-2591-2601-2611-2621-2631-2641-2651-2661-2671-2681-2691-2701-2711-2721-2731-2741-2751-2761-2771-2781-2791-2801-2811-2821-2831-2841-2851-2861-2871-2881-2891-290 | Ph(4-OMe)5-Cl N OMe OMeBn 5-Cl N OMe OMeCF2Cl 5-Me N OMe OMeCF2Cl 5-Cl N OMe OMeCF2Cl 5-Br N OMe OMeCF2Cl 5-OMe N OMe OMeCH2Cl 5-Me N OMe OMeCH2Cl 5-Cl N OMe OMeCH2Cl 5-Br N OMe OMeCH2Cl 5-OMe N OMe OMeC2F5 5-Me N OMe OMeC2F5 5-Cl N OMe OMeC2F5 5-Br N OMe OMeC2F5 5-OMe N OMe OMePh(4-Cl) 5-OMe CH OMe OMeCH2OMe 5-Cl N OMe OMeCF3 5-Me N OMe OEtCF3 5-Cl N OMe OEtCF3 5-Br N OMe OEtCF2Cl 5-Cl N OMe OEtCF2Cl 5-Br N OMe OEtCF2Cl 5-Me N OMe OEtCH2Cl 5-Cl N OMe OEtCH2Cl 5-Br N OMe OEtCH2Cl 5-Me N OMe OEtC2F5 5-Cl N OMe OEtC2F5 5-Br N OMe OEtC2F5 5-Me N OMe OEtMe 5-F CH OEt OEtMe 5-Cl CH OEt OEtMe 5-Br CH OEt OEtMe 5-Me CH OEt OEtMe 5-CF3 CH OEt OEt | 187-200183-186 |
表45
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-2911-2921-2931-2941-2951-2961-2971-2981-2991-3001-3011-3021-3031-3041-3051-3061-3071-3081-3091-3101-3111-3121-3131-3141-3151-3161-3171-3181-3191-3201-3211-3221-323 | Me 5-F N OEt OEtMe 5-Cl N OEt OEtMe 5-Br N OEt OEtMe 5-Me N OEt OEtMe 5-CF3 N OEt OEtCF3 5-F CH OEt OEtCF3 5-Cl CH OEt OEtCF3 5-Br CH OEt OEtCF3 5-Me CH OEt OEtCF3 5-CF3 CH OEt OEtCF3 5-OMe N OEt OEtCF3 5-Cl N OEt OEtCF3 5-Br N OEt OEtCF3 5-Me N OEt OEtCF3 5-CF3 N OEt OEtPh H N OEt OEtPh(4-Cl) H N OEt OEtPh(4-Me) H N OEt OEtPh(4-OMe) H N OEt OEtPh 5-Cl N OEt OEtPh(4-Cl) 5-Cl N OEt OEtPh(4-Me) 5-Cl N OEt OEtPh(4-OMe) 5-Cl N OEt OEtPh 5-Br N OEt OEtPh(4-Cl) 5-Br N OEt OEtPh(4-Me) 5-Br N OEt OEtPh(4-OMe) 5-Br N OEt OEtH H CH OPr OPrMe 5-Cl N OPr OPrMe 5-Br N OPr OPrMe 5-Me N OPr OPrCF3 5-Cl N OPr OPrCF3 5-Br N OPr OPr | 159-161194-197191-194201-204150-153 |
表46
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-3241-3251-3261-3271-3281-3291-3301-3311-3321-3331-3341-3351-3361-3371-3381-3391-3401-3411-3421-3431-3441-3451-3461-3471-3481-3491-3501-3511-3521-3531-3541-3551-356 | CF3 5-Me N OPr OPrH H CH OPr-i OPr-iMe 5-Cl CH OPr-i OPr-iMe 5-Me CH OPr-i OPr-iMe 5-Cl N OPr-i OPr-iMe 5-Br N OPr-i OPr-iMe 5-Me N OPr-i OPr-iCF3 5-Cl N OPr-i OPr-iCF3 5-Br N OPr-i OPr-iCF3 5-Me N OPr-i OPr-iMe 5-Cl N OCH2CH＝CH2 OCH2CH＝CH2Me 5-Br N OCH2CH＝CH2 OCH2CH＝CH2Me 5-Me N OCH2CH＝CH2 OCH2CH＝CH2CF3 5-Cl N OCH2CH＝CH2 OCH2CH＝CH2CF3 5-Br N OCH2CH＝CH2 OCH2CH＝CH2CF3 5-Me N OCH2CH＝CH2 OCH2CH＝CH2Me 5-Cl N OCH2C≡CH OCH2C≡CHMe 5-Br N OCH2C≡CH OCH2C≡CHMe 5-Me N OCH2C≡CH OCH2C≡CHCF3 5-Cl N OCH2C≡CH OCH2C≡CHCF3 5-Br N OCH2C≡CH OCH2C≡CHCF3 5-Me N OCH2C≡CH OCH2C≡CHMe 5-Cl CH OCH2CN OCH2CNMe 5-Me CH OCH2CN OCH2CNMe 5-Cl N OCH2CN OCH2CNMe 5-Br N OCH2CN OCH2CNMe 5-Me N OCH2CN OCH2CNCF3 5-Cl N OCH2CN OCH2CNCF3 5-Br N OCH2CN OCH2CNCF3 5-Me N OCH2CN OCH2CNMe 5-Cl CH OCH2CH2OMe OCH2CH2OMeMe 5-Me CH OCH2CH2OMe OCH2CH2OMeH 5-Br N OCH2CH2OMe OCH2CH2OMe | 198-201121-124 |
表47
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-3571-3581-3591-3601-3611-3621-3631-3641-3651-3661-3671-3681-3691-3701-3711-3721-3731-3741-3751-3761-3771-3781-3791-3801-3811-3821-3831-3841-3851-3861-3871-3881-389 | Me 5-Cl N OCH2CH2OMe OCH2CH2OMeMe 5-Br N OCH2CH2OMe OCH2CH2OMeMe 5-Me N OCH2CH2OMe OCH2CH2OMeCF3 5-Cl N OCH2CH2OMe OCH2CH2OMeCF3 5-Br N OCH2CH2OMe OCH2CH2OMeCF3 5-Me N OCH2CH2OMe OCH2CH2OMeH 5-Br N OCH2Pr-c OCH2Pr-cMe 5-Cl N OCH2Pr-c OCH2Pr-cMe 5-Br N OCH2Pr-c OCH2Pr-cMe 5-Me N OCH2Pr-c OCH2Pr-cCF3 5-Cl N OCH2Pr-c OCH2Pr-cCF3 5-Br N OCH2Pr-c OCH2Pr-cCF3 5-Me N OCH2Pr-c OCH2Pr-cH H CH OBn OBnH H N OBn OBnH H N OBn(4-Cl) OBn(4-Cl)H H N OBn(4-Me) OBn(4-Me)H H N OBn(4-OMe) OBn(4-OMe)H H CH OMe OPhH H N OMe OPhH H N OMe OPh(4-Cl)H H N OMe OPh(4-Me)H H N OMe OPh(4-OMe)H H CH OMe OCHF2H H N OMe OCHF2Me 5-Cl CH OMe HMe 5-Me CH OMe HMe 5-CF3 CH OMe HMe 5-OMe CH OMe HCF3 5-Cl CH OMe HCF3 5-Me CH OMe HCF3 5-CF3 CH OMe HCF3 5-OMe CH OMe H | 125-128130-133153-156 |
表48
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-3901-3911-3921-3931-3941-3951-3961-3971-3981-3991-4001-4011-4021-4031-4041-4051-4061-4071-4081-4091-4101-4111-4121-4131-4141-4151-4161-4171-4181-4191-4201-4211-422 | CF3 5-Cl CH OEt HCF3 5-Me CH OEt HCF3 5-OMe CH OEt HMe 5-Cl CH OMe MeMe 5-Me CH OMe MeMe 5-CF3 CH OMe MeCF3 5-Cl CH OMe MeCF3 5-Me CH OMe MeCF3 5-OMe CH OMe MeMe 5-Cl N OMe MeMe 5-Me N OMe MeMe 5-CF3 N OMe MeCF3 5-Cl N OMe MeCF3 5-Me N OMe MeCF3 5-OMe N OMe MeCF3 5-Cl N OMe PrCF3 5-Br N OMe PrCF3 5-Me N OMe PrCF3 5-Cl N OMe Pr-cCF3 5-Br N OMe Pr-cCF3 5-Me N OMe Pr-cCF3 5-Cl N OEt Pr-cCF3 5-Me N OEt Pr-cCF3 5-CF3 N OEt Pr-cMe 5-Cl CH OEt MeMe 5-Me CH OEt MeMe 5-CF3 CH OEt MeMe 5-OMe CH OEt MeCF3 5-Cl CH OEt MeCF3 5-Me CH OEt MeCF3 5-OMe CH OEt MeMe 5-Cl N OEt MeMe 5-Br N OEt Me | 125-127192-195149-152103-106136-139 |
表49
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-4231-4241-4251-4261-4271-4281-4291-4301-4311-4321-4331-4341-4351-4361-4371-4381-4391-4401-4411-4421-4431-4441-4451-4461-4471-4481-4491-4501-4511-4521-4531-4541-455 | Me 5-Me N OEt MeMe 5-CF3 N OEt MeCF3 5-Cl N OEt MeCF3 5-Br N OEt MeCF3 5-Me N OEt MeCF3 5-Cl CH OCH2CH＝CH2 MeCF3 5-Me CH OCH2CH＝CH2 MeCF3 5-OMe CH OCH2CH＝CH2 MeCF3 5-Cl N OCH2CH＝CH2 MeCF3 5-Me N OCH2CH＝CH2 MeCF3 5-OMe N OCH2CH＝CH2 MeCF3 5-Me CH SMe MeCF3 5-Cl CH SMe MeCF3 5-Me N SMe MeCF3 5-Cl N SMe MeCF3 5-Cl N OMe EtCF3 5-Br N OMe EtCF3 5-Me N OMe EtCF3 5-Cl N OEt EtCF3 5-Br N OEt EtCF3 5-Me N OEt EtMe 5-Cl N SMe SMeMe 5-Br N SMe SMeMe 5-Me N SMe SMeCF3 5-Cl N SMe SMeCF3 5-Br N SMe SMeCF3 5-Me N SMe SMeMe 5-Cl N OMe SMeMe 5-Br N OMe SMeCF3 5-Cl N OMe SMeCF3 5-Br N OMe SMeCF3 5-Me N OMe SMeMe 5-Me N OMe Ph | 175-178196-199157-160 |
表50
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-4561-4571-4581-4591-4601-4611-4621-4631-4641-4651-4661-4671-4681-4691-4701-4711-4721-4731-4741-4751-4761-4771-4781-4791-4801-4811-4821-4831-4841-4851-4861-4871-488 | CF3 5-Me N OMe PhMe H CH Cl ClMe 4，5-Cl CH Cl ClMe H N Cl ClMe H CH Cl MeMe 5-Cl N NMe2 NMe2CF3 5-Cl N NMe2 NMe2H H CH OMe NMe2H H CBr OMe OMeH H CMe Cl ClMe 5-Me COMe H HMe 5-Cl COMe H HMe 5-Cl CH Me MeMe 5-CF3 CH Me MeMe 5-Cl CH Me CF3Me 5-Me CH Me EtMe 5-Cl CH Me EtCF3 5-Me CH Me EtCF3 5-Cl CH Me EtMe 5-Me CH Me Pr-cMe 5-Cl CH Me Pr-cCF3 5-Me CH Me Pr-cCF3 5-Cl CH Me Pr-cCF3 5-Cl CH C≡CMe MeCF3 5-Cl N C≡CMe MeCF3 5-Cl CH CH＝CH2 MeCF3 5-Cl N CH＝CH3 MeMe 5-Cl CH CHO MeMe 5-Cl N CHO MeMe 5-Cl CH COMe MeMe 5-Cl N COMe MeMe 5-Cl CH CH2OMe MeMe 5-Me CH CH2OMe Me | 219-222219-222 |
表51
| 化合物编号 | X Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 1-4891-4901-4911-4921-4931-4941-495 | Me H CH CN CNMe H CH CN MeMe H N CN CNMe H N CN MeMe H CH SO2Me SO2MeMe H N SO2Me SO2MeMe H CH SO2Me Me |
表52
表53
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 2-252-262-272-282-292-302-312-322-332-342-352-362-372-382-392-402-412-422-432-442-452-462-472-482-492-502-512-522-532-542-55 | 4-Ph(4-Cl) CH OMe OMe4-Ph(4-Me) CH OMe OMe4-Ph(4-OMe) CH OMe OMe4-NO2 CH Ome OMe4-NH2 CH OMe OMe4-MHMe CH OMe OMe4-NMe2 CH OMe OMe4-CN CH OMe OMe5-F CH OMe OMe5-Cl CH OMe OMe5-Me CH OMe OMe5-CF3 CH OMe OMe5-OMe CH OMe OMe5-CO2Me CH OMe OMe5-COPh CH OMe OMe6-Me CH OMe OMe6-Cl CH OMe OMe4，5-Cl2 CH OMe OMe4，5-Me2 CH OMe OMe4，5-(OMe)2 CH OMe OMe4，6-Me2 CH OMe OMe3-Br，5-CF3 CH OMe OMe3-Cl，5-CF3 CH OMe OMe3，4，5-F3 CH OMe OMeH N OMe OMe3-Me N OMe OMe3-Cl N OMe OMe4-F N OMe OMe4-Cl N OMe OMe4-Br N OMe OMe4-I N OMe OMe | 241-244136-139139-142177-180184-187206-208218-221 |
表54
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 2-562-572-582-592-602-612-622-632-642-652-662-672-682-692-702-712-722-732-742-752-762-772-782-792-802-812-822-832-842-852-86 | 4-Me N OMe OMe4-Et N OMe OMe4-Pr N OMe OMe4-CF3 N OMe OMe4-Bu-t N OMe OMe4-C≡CBu-t N OMe OMe4-OMe N OMe OMe4-OEt N OMe OMe4-OPr N OMe OMe4-OCF3 N OMe OMe4-OCH2CH＝CH2 N OMe OMe4-OCH2C≡CH N OMe OMe4-OPh N OMe OMe4-SMe N OMe OMe4-COPh N OMe OMe4-CO2Me N OMe OMe4-Ph N OMe OMe4-Ph(4-Cl) N OMe OMe4-Ph(4-Me) N OMe OMe4-Ph(4-OMe) N OMe OMe4-NO2 N OMe OMe4-NH2 N OMe OMe4-NHMe N OMe OMe4-NMe2 N OMe OMe4-CN N OMe OMe5-F N OMe OMe5-Cl N OMe OMe5-Me N OMe OMe5-CF3 N OMe OMe5-OMe N OMe OMe5-NO2 N OMe OMe | 189-191146-149170-173118-121117-120197-199119-122221-224289-292155-158189-201151-154 |
表55
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 2-872-882-892-902-912-922-932-942-952-962-972-982-992-1002-1012-1022-1032-1042-1052-1062-1072-1082-1092-1102-1112-1122-1132-1142-1152-1162-117 | 5-CO2Et N OMe OMe5-COPh N OMe OMe6-Me N OMe OMe6-Cl N OMe OMe4，5-Cl2 N OMe OMe4，5-Me2 N OMe OMe4，5-(OMe)2 N OMe OMe3-Br，5-CF3 N OMe OMe3-Cl，5-CF3 N OMe OMe3，4，5-F3 N OMe OMe4-Me N OMe OEt4-Cl N OMe OEt4-Br N OMe OEtH CH OEt OEt4-F CH OEt OEt4-Cl CH OEt OEt4-Br CH OEt OEt4-Me CH OEt OEt4-CF3 CH OEt OEt4-F N OEt OEt4-Cl N OEt OEt4-Br N OEt OEt4-Me N OEt OEt4-CF3 N OEt OEt4-Cl N OPr OPr4-Cl CH OPr-i OPr-i4-Me CH OPr-i OPr-i4-Cl N OPr-i OPr-i4-Br N OPr-i OPr-i4-Cl N OCH2CH＝CH2 OCH2CH＝CH24-Br N OCH2CH＝CH2 OCH2CH＝CH2 | 173-175130-13292-95131-134147-149147-150134-137 |
表56
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 2-1182-1192-1202-1212-1222-1232-1242-1252-1262-1272-1282-1292-1302-1312-1322-1332-1342-1352-1362-1372-1382-1392-1402-1412-1422-1432-1442-1452-1462-1472-148 | 4-Cl N OCH2C≡CH OCH2C≡CH4-Br N OCH2C≡CH OCH2C≡CH4-Cl N OCH2CN OCH2CN4-Br N OCH2CN OCH2CN4-Br N OCH2CH2OMe OCH2CH2OMe4-Cl N O CH2CH2OMe OCH2CH2OMe4-Br N OCH2Pr-c OCH2Pr-c4-Cl N OCH2Pr-c OCH2Pr-cH CH OBn OBnH N OBn OBnH N OBn(4-Cl) OBn(4-Cl)H N OBn(4-Me) OBn(4-Me)H N OBn(4-OMe) OBn(4-OMe)H CH OMe OPhH N OMe OPhH N OMe OPh(4-Cl)H N OMe OPh(4-Me)H N OMe OPh(4-OMe)H CH OMe OCHF2H N OMe OCHF24-Cl CH OMe H4-Me CH OMe H4-Cl CH OEt H4-Me CH OEt H4-Cl CH OMe Me4-Me CH OMe Me4-CF3 CH OMe Me4-Cl N OMe Me4-Me N OMe Me4-Cl N OMe Pr4-Me N OMe Pr | 65-68136-139136-139118-11999-100155-158116-119 |
表57
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 2-1492-1502-1512-1522-1532-1542-1552-1562-1572-1582-1592-1602-1612-1622-1632-1642-1652-1662-1672-1682-1692-1702-1712-1722-1732-1742-1752-1762-1772-1782-179 | 4-Cl N OMe Pr-c4-Br N OMe Pr-c4-Me N OMe Pr-c4-Cl N OEt Pr-c4-Me N OEt Pr-c4-Cl N OMe Et4-Br N OMe Et4-Me N OMe Et4-Cl N OEt Et4-Br N OEt Et4-Me N OEt Et4-Me N OPr Me4-Cl N OPr Me4-Me CH Me Et4-Cl CH Me Et4-Me CH Et Et4-Cl CH Et Et4-Me N Me SMe4-Cl N SMe SMe4-Br N SMe SMe4-Me N SMe SMe4-Cl N OMe SMe4-Me N OMe SMe4-Me N OMe Ph4-Cl N NMe2 NMe2H CBr OMe OMeH CMe Cl Cl4-Me COMe H H4-Cl COMe H H4-Me N Cl Ph4-Cl N Cl Ph | 130133109-112113-116175-17875-7864-67174-177179-182165-168＞300106-109 |
表58
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 2-1802-1812-1822-1832-1842-1852-1862-1872-1882-1892-1902-1912-1922-1932-1942-1952-196 | 4-Cl CH C≡CMe Me4-Cl N C≡CMe Me4-Cl CH CH＝CH2 Me4-Cl N CH＝CH2 Me4-Cl CH CHO Me4-Cl N CHO Me4-Cl CH COMe Me4-Cl N COMe Me4-Cl CH CH2OMe Me4-Me CH CH2OMe MeH CH CN CNH CH CN MeH N CN CNH N CN MeH CH SO2Me SO2MeH N SO2Me SO2MeH CH SO2Me Me |
表59
表60
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 3-253-263-273-283-293-303-313-323-333-343-353-363-373-383-393-403-413-423-433-443-453-463-473-483-493-503-513-523-533-543-55 | 4-Ph(4-Cl) CH OMe OMe4-Ph(4-Me) CH OMe OMe4-Ph(4-OMe) CH OMe OMe4-NO2 CH OMe OMe4-NH2 CH OMe OMe4-NHMe CH OMe OMe4-NMe2 CH OMe OMe4-CN CH OMe OMe5-F CH OMe OMe5-Cl CH OMe OMe5-Me CH OMe OMe5-CF3 CH OMe OMe5-OMe CH OMe OMe5-CO2Me CH OMe OMe5-COPh CH OMe OMe6-Me CH OMe OMe6-Cl CH OMe OMe4，5-Cl2 CH OMe OMe4，6-Me2 CH OMe OMe4，5-Me2 CH OMe OMe4，5-(OMe)2 CH OMe OMe3-Br，5-CF3 CH OMe OMe3-Cl，5-CF3 CH OMe OMe3，4，5-F3 CH OMe OMeH N OMe OMe3-Me N OMe OMe3-Cl N OMe OMe4-F N OMe OMe4-Cl N OMe OMe4-Br N OMe OMe4-I N OMe OMe | 166-169124-12591-94145-147152-155183-186202-205200-203191-194 |
表61
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 3-563-573-583-593-603-613-623-633-643-653-663-673-683-693-703-713-723-733-743-753-763-773-783-793-803-813-823-833-843-853-86 | 4-Me N OMe OMe4-Et N OMe OMe4-Pr N OMe OMe4-CF3 N OMe OMe4-Bu-t N OMe OMe4-C≡CBu-t N OMe OMe4-OMe N OMe OMe4-OEt N OMe OMe4-OPr N OMe OMe4-OCF3 N OMe OMe4-OCH2CH＝CH2 N OMe OMe4-OCH2C≡CH N OMe OMe4-OPh N OMe OMe4-SMe N OMe OMe4-COPh N OMe OMe4-CO2Me N OMe OMe4-Ph N OMe OMe4-Ph(4-Cl) N OMe OMe4-Ph(4-Me) N OMe OMe4-Ph(4-OMe) N OMe OMe4-NO2 N OMe OMe4-NH2 N OMe OMe4-NHMe N OMe OMe4-NMe2 N OMe OMe4-CN N OMe OMe5-F N OMe OMe5-Cl N OMe OMe5-Me N OMe OMe5-CF3 N OMe OMe5-OMe N OMe OMe5-NO2 N OMe OMe | 180-183123-126136-139177-180140-143161-164182-185175-178197-200115-118215-218131-134 |
表62
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 3-873-883-893-903-913-923-933-943-953-963-973-983-993-1003-1013-1023-1033-1043-1053-1063-1073-1083-1093-1103-1113-1123-1133-1143-1153-1163-117 | 5-CO2Et N OMe OMe5-COPh N OMe OMe6-Me N OMe OMe6-Cl N OMe OMe4，5-Cl2 N OMe OMe425-Me2 N OMe OMe4，5-(OMe)2 N OMe OMe3-Br，5-CF3 N OMe OMe3-Cl，5-CF3 N OMe OMe3，4，5-F3 N OMe OMe4-Me N OMe OEt4-Cl N OMe OEt4-Br N OMe OEtH CH OEt OEt4-F CH OEt OEt4-Cl CH OEt OEt4-Br CH OEt OEt4-Me CH OEt OEt4-CF3 CH OEt OEt4-F N OEt OEt4-Cl N OEt OEt4-Br N OEt OEt4-Me N OEt OEt4-Bu-t N OEt OEt4-OMe N OEt OEt4-CF3 N OEt OEt4-Cl N OPr OPr4-Cl CH OPr-i OPr-i4-Me CH OPr-i OPr-i4-Cl N OPr-i OPr-i4-Br N OPr-i OPr-i | 134-137132-135140-142146-148167-170163-166172-175158-161128-129128-129145-148179-182 |
表63
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 3-1183-1193-1203-1213-1223-1233-1243-1253-1263-1273-1283-1293-1303-1313-1323-1333-1343-1353-1363-1373-1383-1393-1403-1413-1423-1433-1443-1453-1463-1473-148 | 4-Cl N OCH2CH＝CH2 OCH2CH＝CH24-Br N OCH2CH＝CH2 OCH2CH＝CH24-Cl N OCH2C≡CH OCH2C≡CH4-Br N OCH2C≡CH OCH2C≡CH4-Cl N OCH2CN OCH2CN4-Br N OCH2CN OCH2CN4-Br N OCH2CH2OMe OCH2CH2OMe4-Cl N OCH2CH2OMe OCH2CH2OMe4-Br N OCH2Pr-c OCH2Pr-c4-Cl N OCH2Pr-c OCH2Pr-cH CH OBn OBnH N OBn OBnH N OBn(4-Cl) OBn(4-Cl)H N OBn(4-Me) OBn(4-Me)H N OBn(4-OMe) OBn(4-OMe)H CH OMe OPhH N OMe OPhH N OMe OPh(4-Cl)H N OMe OPh(4-Me)H N OMe OPh(4-OMe)H CH OMe OCHF2H N OMe OCHF24-Cl CH OMe H4-Me CH OMe H4-Cl CH OEt H4-Me CH OEt H4-Cl CH OMe Me4-Me CH OMe Me4-CF3 CH OMe Me4-Cl N OMe Me4-Me N OMe Me | 156-159136-139126-129113-115103-105134-137202-205 |
表64
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 3-1493-1503-1513-1523-1533-1543-1553-1563-1573-1583-1593-1603-1613-1623-1633-1643-1653-1663-1673-1683-1693-1703-1713-1723-1733-1743-1753-1763-1773-1783-179 | 4-Cl N OMe Pr4-Me N OMe Pr4-Cl N OMe Pr-c4-Br N OMe Pr-c4-Me N OMe Pr-c4-Cl N OEt Pr-c4-Me N OEt Pr-c4-Cl N OMe Et4-Br N OMe Et4-Me N OMe Et4-Cl N OEt Et4-Br N OEt Et4-Me N OEt Et4-Me N OPr Me4-Cl N OPr Me4-Me CH Me Et4-Cl CH Me Et4-Me CH Et Et4-Cl CH Et Et4-Me N Me SMe4-Cl N SMe SMe4-Br N SMe SMe4-Me N SMe SMe4-Cl N OMe SMe4-Me N OMe SMe4-Me N OMe Ph4-Cl N NMe2 NMe2H CBr OMe OMeH CMe Cl Cl4-Me COMe H H4-Cl COMe H H | 133-136163-16556-59163-166105-108155-158162-165171-17492-9591-94180-183192-195170-173176-179 |
表65
| 化合物编号 | Yn A R1 R2 | 熔点(℃)或折射率(nD 20) |
| 3-1803-1813-1823-1833-1843-1853-1863-1873-1883-1893-1903-1913-1923-1933-1943-1953-1963-1973-198 | 4-Me N Cl Ph4-Cl N Cl Ph4-Cl CH C≡CMe Me4-Cl N C≡CMe Me4-Cl CH CH＝CH2 Me4-Cl N CH＝CH2 Me4-Cl CH CHO Me4-Cl N CHO Me4-Cl CH COMe Me4-Cl N COMe Me4-Cl CH CH2OMe Me4-Me CH CH2OMe MeH CH CN CNH CH CN MeH N CN CNH N CN MeH CH SO2Me SO2MeH N SO2Me SO2MeH CH SO2Me Me |
实施发明的最佳状态
下面用实施例对本发明化合物的制备方法、制剂方法及用途作具体说明。
<制备例1>
1-(4-甲氧基嘧啶-2-基)-苯并咪唑(化合物编号I-667)
将苯并咪唑(0.50g)溶于二甲基甲酰胺(10ml)，于室温下加入氢化钠(60％纯度，油性)(0.18g)。搅拌1小时后，于室温下加入2-氯-4-甲氧基嘧啶(0.62g)，搅拌3小时。加冰水，用乙酸乙酯萃取，用饱和食盐水洗涤后，以无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色粉末(熔点114-116℃)目的物0.40g。
<制备例2>
1-(4，6-二甲氧基嘧啶-2-基)-2-甲硫基苯并咪唑(化合物编号I-4)
将2-甲硫基苯并咪唑(0.50g)溶于二甲基甲酰胺(10ml)，于室温下加入氢化钠(60％纯度，油性)(0.13g)。搅拌1小时后，于室温下加入2-甲基磺酰基-4，6-二甲氧基嘧啶(0.67g)，搅拌8小时。加冰水，用乙酸乙酯萃取，用饱和食盐水洗涤后，以无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色粉末(熔点135-137℃)目的物0.80g。
<制备例3>
1-(4，6-二甲氧基嘧啶-2-基)-2-甲基磺酰基苯并咪唑(化合物编号I-5)
将1-(4，6-二甲氧基嘧啶-2-基)-2-甲硫基苯并咪唑(0.70g)、间氯过苯甲酸(1.30g)溶于氯仿(30ml)，室温搅拌3小时。反应液用5％碳酸钾水溶液、水洗涤，有机溶剂层用无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色粉末(熔点114-117℃)目的物0.50g。
<制备例4>
1-(4，6-二甲氧基嘧啶-2-基)-2-甲氧基苯并咪唑(化合物编号I-18)
将1-(4，6-二甲氧基嘧啶-2-基)-2-甲基磺酰基苯并咪唑(0.40g)溶于四氢呋喃(20ml)，于冰冷却下加入甲醇钠(0.50g)，搅拌1小时。加冰水，用乙酸乙酯萃取、饱和食盐水洗涤后，用无水硫酸镁干燥。蒸去溶剂后，混合物用硅胶柱层析精制，得到白色粉末(熔点121-122℃)目的物0.40g。
<制备例5>
1-(4，6-二甲氧基嘧啶-2-基)-2，5-二甲基苯并咪唑(化合物编号I-186)
将N’-(4，6-二甲氧基嘧啶-2-基)-4-甲基苯-1，2-二胺(2.50g)溶于乙酸(20ml)、乙酸酐(10ml)，回流4小时。加水，滤取结晶，水洗后干燥。用乙醇重结晶，得到白色羽毛状结晶(熔点163-166℃)目的物1.90g。
<制备例6>
2-氨基-1-(4，6-二甲氧基嘧啶-2-基)-5-甲基苯并咪唑(化合物编号I-362)
将N’-(4，6-二甲氧基嘧啶-2-基)-4-甲基苯-1，2-二胺(2.00g)溶于乙醇，室温下加入溴化氰(1.00g)，60℃搅拌1小时。加水，滤取结晶，水洗后干燥。得到白色粉末(熔点300℃以上)目的物2.03g。
<制备例7>
2-氯-1-(4，6-二甲氧基嘧啶-2-基)-5-甲基苯并咪唑(化合物编号I-258)
将2-氨基-1-(4，6-二甲氧基嘧啶-2-基)-5-甲基苯并咪唑(1.67g)、氯化铜(II)(0.94g)悬浮于乙腈(30ml)，室温下加入亚硝酸叔丁酯(0.90g)，回流30分钟。加水，用乙酸乙酯萃取，饱和食盐水洗涤后用无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色羽毛状结晶(熔点145-148℃)目的物1.48g。
<制备例8>
1-(4，6-二甲氧基嘧啶-2-基)-5-甲基-2-三氟甲基苯并咪唑(化合物编号I-298)
将2-(4，6-二甲氧基嘧啶-2-基)氨基-5-甲基三氟乙酰苯胺(0.60g)和对甲苯磺酸(0.05g)溶于甲苯(30ml)，回流5小时。加水、乙酸乙酯，将有机层用饱和碳酸氢钠溶液、饱和食盐水洗涤后用无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色粉末(熔点93-96℃)目的物0.56g。
<制备例9>
1-(4，6-二氯-[1，3，5]三嗪-2-基)-2-甲基苯并咪唑(化合物编号I-1066)
将2-甲基苯并咪唑(5.0g)溶于四氢呋喃(50ml)，于室温下加入氢化钠(60％纯度，油性)(1.6g)。搅拌1小时后，于室温下加入氰脲酰氯(7.0g)，搅拌3小时。加冰水，用乙酸乙酯萃取、饱和食盐水洗涤后，用无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色粉末(熔点300℃以上)目的物2.6g。
<制备例10>
1-(4，6-二甲硫基-[1，3，5]三嗪-2-基)-2-甲基苯并咪唑(化合物编号I-1042)
将1-(4，6-二氯-[1，3，5]三嗪-2-基)-2-甲基苯并咪唑(0.5g)溶于甲醇(10ml)，于室温下加入甲硫醇钠的15％水溶液(0.25g)，搅拌1小时。反应结束后，将反应液倾入冰水中，滤取析出的结晶，水洗后，干燥，得到白色粉末(熔点176-179℃)目的物0.46g。
<制备例11>
5-氯-1-(4，6-二甲氧基-[1，3，5]三嗪-2-基)-2-甲基苯并咪唑(化合物编号I-215)
将4-氯-N’-(4，6-二甲氧基-[1，3，5]三嗪-2-基)苯-1，2-二胺(0.5g)溶于乙酸(10ml)、乙酸酐(10ml)，回流4小时。加水，滤取析出的结晶，水洗后干燥。用乙醇重结晶，得到白色羽毛状结晶(熔点173-176℃)目的物0.47g。
<制备例12>
5-氯-1-(4，6-二甲氧基-[1，3，5]三嗪-2-基)-2-甲基苯并咪唑(化合物编号I-215)
将2-硝基-4-氯-N-(4，6-二甲氧基-[1，3，5]三嗪-2-基)苯胺(0.5g)、铁粉(0.3g)溶于乙酸(10ml)、乙酸酐(5ml)，回流4小时。将反应混合物冷却至室温后过滤。滤液减压浓缩，残渣中加水，滤取结晶，水洗后干燥。用乙醇重结晶，得到白色羽毛状结晶(熔点173-176℃)目的物0.39g。
<制备例13>
2-氨基-5-氯-1-(4，6-二甲氧基-[1，3，5]三嗪-2-基)苯并咪唑(化合物编号I-368)
将4-氯-N’-(4，6-二甲氧基-[1，3，5]三嗪-2-基)苯-1，2-二胺(1.5g)溶于乙醇(50ml)，于室温下加入溴化氰(0.6g)，60℃搅拌1小时。加水，滤取结晶，水洗后干燥。得到桃色粉末(熔点293-296℃)目的物1.2g。
<制备例14>
2，5-二氯-1-(4，6-二甲氧基-[1，3，5]三嗪-2-基)苯并咪唑(化合物编号I-277)
将2-氨基-5-氧-1-(4，6-二甲氧基-[1，3，5]三嗪-2-基)苯并咪唑(1.1g)、氯化铜(II)(0.6g)悬浮于乙腈(50ml)，于室温下加入亚硝酸叔丁酯(0.5g)，回流30分钟。加水，用乙酸乙酯萃取、饱和食盐水洗涤后，用无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色羽毛状结晶(熔点146-149℃)目的物0.5g。
<制备例15>
1-(4，6-二甲氧基-[1，3，5]三嗪-2-基)-5-甲基-2-三氟甲基苯并咪唑(化合物编号I-312)
将2-(4，6-二甲氧基-[1，3，5]三嗪-2-基)氨基-5-甲基三氟乙酰苯胺(1.0g)和对甲苯磺酸(0.05g)溶于氯苯(30ml)，回流5小时。加水、乙酸乙酯，有机层用饱和碳酸氢钠溶液、饱和食盐水洗涤后用无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色粉末(熔点137-140℃)目的物0.23g。
下面列出若干本发明化合物的1H-NMR(CDCl3/TMS，δ(ppm))数据。
表66
| 化合物编号 | 1H-NMRδ值(ppm) 溶剂 CDCl3 |
| I-30I-34I-840I-872I-906I-907I-959I-960 | 2.99(6H，s)；4.03(6H，s)；5.99(1H，s)；7.03-7.09(1H，m)；7.17-7.22(1H，m)；7.48-7.51(1H，m)；7.84-7.85(1H，m)；8.01(1H，s)3.64(6H，s)；5.92(1H，s)；7.42-7.36(5H，m)；7.56-7.60(2H，m)；7.58-7.88(1H，m)；8.20-8.23(1H，m)1.41(6H，d，J＝6.3Hz)；2.52(3H，s)；2.98(3H，s)；5.39-5.47(1H，m)；6.46(1H，s)；7.26-7.33(2H，m)；7.69-7.72(1H，m)；8.25-8.28(1H，m)1.01(3H，t，J＝7.5Hz)；1.49-1.57(2H，m)；1.80-1.87(2H，m)；2.51(3H，s)；4.50(2H，t，J＝6.57Hz)；6.45(1H，s)；7.33-7.43(2H，m)；7.82-7.85(1H，m)；8.55-8.59(1H，m)；9.05(1H，s)1.66-2.11(8H，m)；2.45(3H，s)；5.51-5.56(1H，m)；6.36(1H，s)；7.28-7.41(2H，m)；7.81-7.83(1H，m)；8.45-8.52(1H，m)；9.05(1H，s)1.65-2.04(8H，m)；2.51(3H，s)；3.98(3H，s)；5.51-5.55(1H，m)；6.46(1H，s)；7.26-7.34(2H，m)；7.68-7.73(1H，m)；8.25-8.31(1H，m)1.03(3H，t，J＝7.41Hz)；1.81-1.89(2H，m)；2.76(2H，t，J＝7.14Hz)；3.00(3H，s)；4.08(3H，s)；6.51(1H，s)；7.27-7.33(2H，m)；7.70-7.73(1H，m)；8.28-8.34(1H，m)1.03(3H，t，J＝7.29Hz)；1.81-1.89(2H，m)；2.77(2H，t，J＝7.29Hz)；4.07(3H，s)；6.58(1H，s)；7.30-7.37(2H，m)；7.71-7.74(1H，m)；8.00-8.05(1H，m) |
下面列出本发明化合物合成中间体的制备例。
<制备例16>
N-(4，6-二甲氧基嘧啶-2-基)-4-甲基-2-硝基苯胺(化合物编号2-6)
将N-甲酰基-4-甲基-2-硝基苯胺(25.00g)溶于二甲基甲酰胺(400ml)，于室温下加入氢化钠(60％纯度，油性)(6.11g)。搅拌10分钟后，于室温下加入2-甲基磺酰基-4，6-二甲氧基嘧啶(30.28g)，搅拌3小时。加入10％NaOH水溶液，滤取结晶，水洗后干燥，得到黄色粉末(熔点158-161℃)目的物37.50g。
<制备例17>
N’-(4，6-二甲氧基嘧啶-2-基)-4-甲基苯-1，2-二胺(化合物编号3-6)
将N-(4，6-二甲氧基嘧啶-2-基)-4-甲基-2-硝基苯胺(37.50g)溶于乙酸乙酯(600ml)，加入10％钯炭(3.75g)。在室温、常压和氢气氛围下搅拌4小时后过滤。蒸去滤液的溶剂，得到白色粉末(熔点128-129℃)目的物32.70g。
<制备例18>
2-(4，6-二甲氧基嘧啶-2-基)氨基-5-甲基三氟乙酰苯胺(化合物编号3-196)
将N’-(4，6-二甲氧基嘧啶-2-基)-4-甲基苯-1，2-二胺(0.80g)溶于吡啶(10ml)，在冰盐冷却下加入三氟乙酸酐(0.97g)。搅拌1小时后，加稀盐酸，用乙酸乙酯萃取，稀盐酸、饱和食盐水洗涤后，用无水硫酸镁干燥。蒸去溶剂后，残渣用硅胶柱层析精制，得到白色粉末(熔点144-147℃)目的物0.88g。
<制备例19>
N-(4，6-二甲氧基-[1，3，5]三嗪-2-基)-4-甲基-2-硝基苯胺(化合物编号2-56)
将N-甲酰基-4-甲基-2-硝基苯胺(7.2g)溶于四氢呋喃(50ml)，于室温下加入氢化钠(60％纯度，油性)(2.0g)。搅拌10分钟后，于室温下加入2-氯-4，6-二甲氧基[1，3，5]三嗪(7.0g)，搅拌3小时。加入10％NaOH水溶液，滤取结晶，水洗后干燥，得到黄色粉末(熔点189-191℃)目的物10.0g。
<制备例20>
N’-(4，6-二甲氧基-[1，3，5]三嗪-2-基)-4-甲基苯-1，2-二胺(化合物编号3-56)
将N-(4，6-二甲氧基-[1，3，5]三嗪-2-基)-4-甲基-2-硝基苯胺(10g)溶于乙酸乙酯(50ml)和水(50ml)，加铁10g和乙酸(2ml)，回流2小时。滤去不溶物，用饱和食盐水洗涤乙酸乙酯层后，用无水硫酸镁干燥。蒸去溶剂，得到白色粉末(熔点180-183℃)目的物8.8g。
<制备例21)
2-(4，6-二甲氧基-[1，3，5]三嗪-2-基)氨基-5-甲基三氟乙酰苯胺(化合物编号1-210)
将N’-(4，6-二甲氧基-[1，3，5]三嗪-2-基)-4-甲基苯-1，2-二胺(1.0g)溶于吡啶(50ml)，于冰盐冷却下，加入三氟乙酸酐(0.8g)。搅拌1小时后，加稀盐酸，用乙酸乙酯萃取，稀盐酸、饱和食盐水洗涤后，用无水硫酸镁干燥。蒸去溶剂，残渣用硅胶柱层析精制，得到白色粉末(熔点195-198℃)目的物1.3g。
<制备例22>
4-氯-N-(4，6-二甲氧基-[1，3，5]三嗪-2-基)-2-硝基苯胺(化合物编号2-53)
将4-氯-2-硝基苯胺(5.0g)、碳酸氢钠(3.6g)溶于四氢呋喃(50ml)，加入氰脲酰氯(8.0g)，搅拌8小时。在反应液中加入28％甲醇钠(11.2g)，回流1小时。加水，用乙酸乙酯萃取、饱和食盐水洗涤后，用无水硫酸镁干燥。蒸去溶剂，残渣用乙醇重结晶，得到黄色粉末(熔点206-208℃)目的物6.3g。
本发明的农业/园艺用杀菌剂含有通式[I]所示三嗪基苯并咪唑衍生物作为有效成分。本发明化合物用作农业/园艺用杀菌剂时，根据其目的，可将有效成分以适当的剂型加以使用。通常将有效成分用惰性液体或固体载体稀释，根据需要可在其中加入表面活性剂等，以粉剂、可湿性粉剂、乳剂、颗粒剂等剂型加以使用。
作为合适的载体，可列举诸如滑石粉、膨润土、粘土、高岭土、硅藻土、白炭黑、蛭石、消石灰、硅砂、硫酸铵、尿素等固体载体，异丙醇、二甲苯、环己酮和甲基萘等液体载体。作为表面活性剂和分散剂，可列举诸如二萘基甲磺酸盐、醇硫酸酯盐、烷芳基磺酸盐、木质素磺酸盐、聚氧乙烯二醇醚、聚氧乙烯烷基芳基醚、聚氧乙烯山梨糖醇酐单烷基化物。作为助剂，可列举羧甲基纤维素等。将这些制剂稀释成适宜的浓度，或直接施用。
本发明的农业/园艺用杀菌剂可以茎叶撒布、土壤施用或水面施用等方式加以使用。有效成分的配比可根据需要加以选择，但在粉剂和颗粒剂的情况下宜为0.1-20％(重量)，在乳剂和可湿性粉剂的情况下宜为5-80％(重量)。
本发明的农业/园艺用杀菌剂的用量根据所用化合物的种类、对象病害、发生倾向、受害程度、环境条件、所用剂型等而变化。例如，粉剂和颗粒剂直接使用时，有效成分宜在每10公亩0.1g～5kg、较佳为1g～1kg的范围内进行选择。在乳剂或可湿性粉剂以液体状使用时，宜在0.1ppm～10,000ppm、较佳为1～3,000ppm范围内进行选择。
本发明的化合物用上述施用方式施用，可防卵菌纲(Oomycetes)、子囊菌类(Ascomycetes)、半知菌纲(Deuteromycetes)和担子菌纲(Basidiomyetes)菌类引起的植物疾病。作为非限制性例子，举出下面的具体菌名：假霜霉属，如古巴假霜霉；白粉菌属，如禾白粉菌(Erysiphegraminis)；黑星菌属，如苹果黑星菌(Venturia inaequalis)；梨形孢(Pyricularia)属，如稻梨形孢(Pyricularia oryzae)；葡萄孢属，如灰色葡萄孢(Botrytis cinerea)；丝核菌属，如茄属丝核菌；柄锈菌属，如隐匿柄锈菌。
根据需要，本发明的化合物还可与杀虫剂、其他杀菌剂、除草剂、植物生长调节剂、肥料等混合使用。下面列举本发明的农业/园艺用杀菌剂的代表性制剂例对制剂方法作具体说明。下面的说明中，“％”表示重量百分率。
制剂例1 粉剂
将化合物(I-45)2％、硅藻土5％和粘土93％均匀混合，粉碎，制成粉剂。
制剂例2可湿性粉剂
将化合物(I-170)50％、硅藻土45％、二萘基甲二磺酸钠2％和木质素磺酸钠3％均匀混合，粉碎，制成可湿性粉剂。
制剂例3 乳剂
将化合物(I-309)30％、环己酮20％、聚氧乙烯烷基芳基醚11％、烷基苯磺酸钙4％和甲基萘35％均匀溶解，制成乳剂。
制剂例4 颗粒剂
将化合物(I-121)5％、月桂醇硫酸酯钠盐2％、木质素磺酸钠5％、羧甲基纤维素2％和粘土86％均匀混合，粉碎。在此混合物中加水20％捏合，用挤压式造粒机加工成14-32目颗粒，然后干燥成颗粒剂。
下面列举试验例对本发明的农业/园艺用杀菌剂显示的效果作具体说明。
试验例1小麦霉病预防效果试验
在9cm×9cm的聚氯乙烯罐中各播种9粒小麦种子(品种：农林61号)，于温室内培育8天。将按制剂例2配制的可湿性粉剂用水稀释成有效成分浓度为500ppm，每罐散布10ml。风干后，接种小麦霉病菌(禾白粉菌，Erysiphegraminis)的孢子，放入20-25℃的温室内。接种10日后检查整个罐第一叶的发病面积，按表67的标准作评价。结果见表68、69。
表67
| 评价 | |
| ABCD | 未见发病发病面积不到25％发病面积25-50％发病面积50％以上 |
表68
| 化合物编号 | 生物效果 | 化合物编号 | 生物效果 | 化合物编号 | 生物效果 |
| I-1I-2I-3I-6I-7I-10I-22I-23I-25I-26I-27I-29I-30I-35I-38I-40I-41I-45I-66I-82I-83I-84I-85I-87I-88I-91I-111I-112I-113I-114I-116I-122I-130I-131I-132I-133I-134I-135I-136I-141I-175I-176I-181I-183I-184I-185I-186I-188 | AAABABAAAABBBBBBAAAABAAABBBBBBBBAAAAAABAAABBAAAA | I-189I-192I-195I-199I-200I-201I-202I-203I-204I-208I-209I-212I-214I-215I-216I-217I-218I-219I-220I-221I-222I-225I-226I-229I-232I-234I-235I-239I-242I-250I-251I-255I-256I-258I-259I-260I-261I-263I-271I-272I-277I-279I-295I-296I-298I-299I-300I-301 | ABBBAABBABBBAAAAAABBBAAABAAAABAAAAAABAAABAAAAAAA | I-307I-309I-310I-311I-312I-313I-314I-315I-316I-318I-321I-327I-332I-333I-334I-335I-336I-346I-358I-359I-360I-362I-364I-366I-368I-369I-375I-376I-377I-378I-379I-380I-381I-388I-389I-394I-400I-404I-405I-406I-423I-424I-438I-457I-458I-461I-462I-465 | AAAAAAABBAAABAAAAAAABAAABBABAAAAAABAABAAAAABAABB |
表69
| 化合物编号 | 生物效果 | 化合物编号 | 生物效果 | 化合物编号 | 生物效果 |
| I-479I-480I-482I-483I-486I-490I-498I-499I-501I-502I-503I-507I-508I-510I-511I-514I-515I-516I-530I-531I-534I-543I-544I-545I-546I-550I-573I-580I-592I-595I-601I-667I-669I-670I-671I-672I-675I-682I-683I-690I-692I-693I-694I-695I-704I-705I-726I-731 | AAAAAAAAAAAABAAAAAAAAAAAAABAABABBBBBBAAABABABABB | I-752I-758I-762I-767I-768I-769I-771I-772I-775I-804I-805I-806I-809I-818I-831I-839I-840I-872I-883I-885I-894I-895I-903I-904I-915I-958I-959I-960I-962I-964I-965I-967I-999I-1004I-1019I-1022I-1043I-1046I-1048I-1058I-1059I-1064I-1071I-1079I-1082I-1085I-1086I-1087 | AAABAAAAAABBBBBABBABBBBBABAAABAAAAAAAAAAABABBABA | I-1088I-1090I-1093I-1094I-1095I-1096I-1098I-1103I-1104I-1106I-1123I-1147 | ABAAAAABBBBB |
本发明的农业/园艺用杀菌剂具有广谱抗菌作用，其中对小麦霉病显示优异的效果。对黄瓜霜霉病、苹果黑星病、稻瘟病、黄瓜灰霉病、稻纹枯病和小麦叶锈病也有高度防治效果，而且，对作物不产生药害，兼具残效性、耐雨性好的特征，因此，作为农业/园艺用杀菌剂是有用的。
Claims (8)
1.通式[I]所示的嘧啶基苯并咪唑或三嗪基苯并咪唑衍生物：
式中，A表示N、或CR3；R1和R2相互独立地表示氢原子，卤原子，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，C1-4卤代烷基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C3-6环烷氧基，C1-4卤代烷氧基，氰基C1-4烷氧基，C1-4烷氧基C1-4烷氧基，C3-6环烷基C1-4烷氧基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基，C1-4烷基羰基，甲酰基，苯基，二-C1-4烷氨基，氰基，或C1-6烷基磺酰基；R3表示氢原子，C1-6烷基，C1-6烷氧基，或卤原子；X表示氢原子，卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-6烷硫基，C1-6烷基磺酰基、苯氧基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷基羰基，C1-4烷氧基羰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，苯胺基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基；Y表示卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-4卤代烷氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4烷基羰基，C1-4烷氧基羰基，苯甲酰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基；n表示0或1-3的整数。
2.如权利要求1所述的嘧啶基苯并咪唑衍生物，其中通式[I]中的A为CR3。
3.如权利要求1所述的三嗪基苯并咪唑衍生物，其中通式[I]中的A为N。
4.如权利要求1所述的嘧啶基苯并咪唑衍生物，其中A为CR3；R1和R2相互独立地表示氢原子，卤原子，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，C1-4卤代烷基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C3-6环烷氧基，C1-4卤代烷氧基，氰基C1-4烷氧基，C1-4烷氧基C1-4烷氧基，C3-6环烷基C1-4烷氧基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4烷基羰基，甲酰基，苯基，氰基，或C1-6烷基磺酰基；R3表示氢原子，C1-6烷基，C1-6烷氧基，或卤原子；X表示氢原子，卤原子，硝基，C1-6烷基，C2-6炔基，C3-6环烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-6烷硫基，C1-6烷基磺酰基，苯氧基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷基羰基，C1-4烷氧基羰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，苯胺基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基；Y表示卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-4卤代烷氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4烷基羰基，C1-4烷氧基羰基，苯甲酰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基；n表示0或1-3的整数。
5.如权利要求1所述的三嗪基苯并咪唑衍生物，其中A为N；R1和R2相互独立地表示氢原子，卤原子，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C3-6环烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，氰基C1-4烷氧基，C1-4烷氧基C1-4烷氧基，C3-6环烷基C1-4烷氧基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4烷基羰基，甲酰基，苯基，氰基，或C1-6烷基磺酰基；X表示氢原子，卤原子，硝基，C1-6烷基，C2-6炔基，C3-6环烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-6烷硫基，C1-6烷基磺酰基，苯氧基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷基羰基，C1-4烷氧基羰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，苯胺基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基；Y表示卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-4卤代烷氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4烷基羰基，C1-4烷氧基羰基，苯甲酰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基；n表示0或1-3的整数。
6.通式[XV]所示的苯胺基三嗪衍生物
式中，R1和R2相互独立地表示氢原子，卤原子，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，C1-4卤代烷基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C3-6环烷氧基，C1-4卤代烷氧基，氰基C1-4烷氧基，C1-4烷氧基C1-4烷氧基，C3-6环烷基C1-4烷氧基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基，C1-4烷基羰基，甲酰基，苯基，二-C1-4烷氨基，氰基，或C1-6烷基磺酰基；R3表示氢原子，C1-6烷基，C1-6烷氧基，或卤原子；R5表示氨基，硝基，或-NHCOX；X表示氢原子，卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-6烷硫基，C1-6烷基磺酰基，苯氧基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷基羰基，C1-4烷氧基羰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，苯胺基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基；Y表示卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-4卤代烷氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4烷基羰基，C1-4烷氧基羰基，苯甲酰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基，n表示0或1-3的整数；但R5为硝基的场合，R1和R2相互独立地表示氢原子，氟，溴，碘，C1-6烷基，C2- 6链烯基，C2-6炔基，C3-6环烷基，C1-4卤代烷基，C2-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C3-6环烷氧基，C1-4卤代烷氧基，氰基C1-4烷氧基，C1-4烷氧基C1-4烷氧基，C3-6环烷基C1-4烷氧基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基，C1-4烷基羰基，甲酰基，苯基，氰基，或C1-6烷基磺酰基。
7.通式〔XVII〕所示苯胺基嘧啶衍生物
式中R1和R2相互独立地表示氢原子，卤原子，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，C1-4卤代烷基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C3-6环烷氧基，C1-4卤代烷氧基，氰基C1-4烷氧基，C1-4烷氧基C1-4烷氧基，C3-6环烷基C1-4烷氧基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基，C1-4烷基羰基，甲酰基，苯基，二-C1-4烷氨基，氰基，或C1-6烷基磺酰基；R3表示氢原子，C1-6烷基，C1-6烷氧基，或卤原子；X表示氢原子，卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C3-6环烷基，可被卤原子、C1-4烷基或C1-4烷氧基取代的苄基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-6烷硫基，C1-6烷基磺酰基、苯氧基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷基羰基，C1-4烷氧基羰基，氨基，一-C1-4烷氨基，二-C1-4烷氨基，苯胺基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯基；Y表示卤原子，硝基，氰基，C1-6烷基，C2-6链烯基，C2-6炔基，C1-6烷氧基，C2-6链烯氧基，C2-6炔氧基，C1-4卤代烷氧基，C1-6烷硫基，C1-4烷氧基C1-4烷基，C1-4卤代烷基，C1-4烷基羰基，烷氧基取代的苯基，或可被卤原子、C1-4烷基或C1-4烷氧基取代的苯氧基；n表示0或1-3的整数。
8.以权利要求1、2、3、4或5所述嘧啶基苯并咪唑或三嗪基苯并咪唑衍生物作为有效成分的农业或园艺用杀菌剂。
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| JP343614/98 | 1998-11-17 | ||
| JP343614/1998 | 1998-11-17 | ||
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| JP39566/1999 | 1999-02-18 | ||
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| JP39566/99 | 1999-02-18 |
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| HUP0104171A2 (hu) | 2002-02-28 |
| IL143157A (en) | 2010-11-30 |
| RU2222536C2 (ru) | 2004-01-27 |
| US20040023966A1 (en) | 2004-02-05 |
| ATE305465T1 (de) | 2005-10-15 |
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