CN1732156A - 二苯基衍生物和它们的作为杀真菌剂的应用 - Google Patents
二苯基衍生物和它们的作为杀真菌剂的应用 Download PDFInfo
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- CN1732156A CN1732156A CNA200380107519XA CN200380107519A CN1732156A CN 1732156 A CN1732156 A CN 1732156A CN A200380107519X A CNA200380107519X A CN A200380107519XA CN 200380107519 A CN200380107519 A CN 200380107519A CN 1732156 A CN1732156 A CN 1732156A
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- Prior art keywords
- sub
- alkyl
- halogen
- compound
- sup
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 4
- 239000000417 fungicide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 190
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 71
- 150000002367 halogens Chemical class 0.000 claims abstract description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 20
- 125000005103 alkyl silyl group Chemical group 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 200
- 239000000203 mixture Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001118 alkylidene group Chemical group 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
- 150000003217 pyrazoles Chemical group 0.000 claims description 8
- 150000003233 pyrroles Chemical class 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- MUGSKSNNEORSJG-UHFFFAOYSA-N 3174-74-1 Chemical compound C1CC=CCO1 MUGSKSNNEORSJG-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
- 150000002240 furans Chemical class 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 4
- JCAIBTLLMPPCQU-UHFFFAOYSA-N 2,3-dihydro-1,4-oxathiine Chemical compound C1CSC=CO1 JCAIBTLLMPPCQU-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 10
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 4
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- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 5
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 125000005529 alkyleneoxy group Chemical group 0.000 abstract 1
- 125000005282 allenyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 43
- 241000196324 Embryophyta Species 0.000 description 37
- -1 suberyl Chemical group 0.000 description 36
- 229910052731 fluorine Inorganic materials 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 238000012360 testing method Methods 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- 239000002585 base Substances 0.000 description 17
- 239000011737 fluorine Substances 0.000 description 17
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 229920002554 vinyl polymer Polymers 0.000 description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
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- CZDLUZXNQXTHNP-UHFFFAOYSA-N CC=C1C(=CC=CC1)C1=CC=CC=C1 Chemical group CC=C1C(=CC=CC1)C1=CC=CC=C1 CZDLUZXNQXTHNP-UHFFFAOYSA-N 0.000 description 8
- 240000005979 Hordeum vulgare Species 0.000 description 8
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 5
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- 230000009885 systemic effect Effects 0.000 description 1
- BGMXQLNMDVZYRF-UHFFFAOYSA-N tert-butylazanium;hydrogen sulfate Chemical compound CC(C)(C)[NH3+].OS([O-])(=O)=O BGMXQLNMDVZYRF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/45—Monoamines
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/76—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/32—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and esterified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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Abstract
杀真菌活性的式(I)化合物:其中Het是取代的5-或6-元的杂环;R1是氢、甲酰基、CO-C1-4烷基、COO-C1-4烷基、C1-4烷氧基(C1-4)亚烷基、CO-C1-4亚烷氧基(C1-4)烷基、炔丙基或丙二烯基;R2、R3、R4和R5各自独立地为氢、卤素、甲基或CF3;每个R6独立地为卤素、甲基或CF3;R7是(Z)mC≡C(Y1)、(Z)mC(Y1)=C(Y2)(Y3)或三(C1-4)烷基甲硅烷基;X是O或S;Y1、Y2和Y3各自独立地为氢、卤素、C1-6烷基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素、羟基、C1-4烷氧基、C1-4卤代烷氧基、C1-4烷硫基、C1-4卤代烷硫基、C1-4烷基氨基、二(C1-4)烷基氨基、C1-4烷氧基羰基、C1-4烷基羰基氧和三(C1-4)烷基甲硅烷基]、C2-4链烯基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素]、C2-4炔基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素]、C3-7环烷基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素、C1-4烷基和C1-4卤代烷基]或三(C1-4)烷基甲硅烷基;Z是C1-4亚烷基[任选地被一个或多个取代基取代,每个取代基独立地选自羟基、氰基、C1-4烷氧基、卤素、C1-4卤代烷基、C1-4卤代烷氧基、C1-4烷硫基、COOH和COO-C1-4烷基];m是0或1;且n是0、1或2;本发明还涉及用于制备这些化合物的新的中间体,涉及含有作为活性成分的至少一种新化合物的农用化学组合物,涉及活性成分或组合物在农业或园艺中控制或预防致植物病微生物、优选真菌对植物的侵染方面的应用。
Description
技术领域
本发明涉及作为具有杀微生物活性、特别是杀真菌活性的活性成分的新的羧酰胺衍生物。本发明还涉及这些活性成分的制备,涉及用作制备这些活性成分的中间体的新的二苯基衍生物,涉及这些新的中间体的制备,涉及含有至少一种新的活性成分的农用化学组合物,涉及这些组合物的制备和活性成分或组合物在农业或园艺中控制或预防致植物病微生物、优选真菌对植物的侵染方面的应用。
背景技术
杀真菌活性的羧酰胺衍生物公开在JP2001072510、JP2001072508、JP2001072507和JP2001302605中。
某些氨基-或卤素-取代的二苯基衍生物公开在DE2205732和JP2001302605中。
发明内容
本发明提供了式(I)化合物:
其中Het是含有1-3个杂原子的5-或6-元杂环,每个杂原子独立地选自氧、氮和硫,条件是:该环不是1,2,3-三唑,该环被1个、2个或3个Ry基团取代;R1是氢、甲酰基、CO-C1-4烷基、COO-C1-4烷基、C1-4烷氧基(C1-4)亚烷基、CO-C1-4亚烷氧基(C1-4)烷基、炔丙基或丙二烯基;R2、R3、R4和R5各自独立地为氢、卤素、甲基或CF3;每个R6独立地为卤素、甲基或CF3;R7是(Z)mC≡C(Y1)、(Z)mC(Y1)=C(Y2)(Y3)或三(C1-4)烷基甲硅烷基;每个Ry独立地为卤素、C1-3烷基、C1-3卤代烷基、C1-3烷氧基(C1-3)亚烷基或氰基;X是O或S;Y1、Y2和Y3各自独立地为氢、卤素、C1-6烷基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素、羟基、C1-4烷氧基、C1-4卤代烷氧基、C1-4烷硫基、C1-4卤代烷硫基、C1-4烷基氨基、二(C1-4)烷基氨基、C1-4烷氧基羰基、C1-4烷基羰基氧和三(C1-4)烷基甲硅烷基]、C2-4链烯基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素]、C2-4炔基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素]、C3-7环烷基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素、C1-4烷基和C1-4卤代烷基]或三(C1-4)烷基甲硅烷基;Z是C1-4亚烷基[任选地被一个或多个取代基取代,每个取代基独立地选自羟基、氰基、C1-4烷氧基、卤素、C1-4卤代烷基、C1-4卤代烷氧基、C1-4烷硫基、COOH和COO-C1-4烷基];m是0或1;且n是0、1或2。
在一个具体的方面,本发明提供了如上定义的式(I)化合物,其中Y1、Y2和Y3各自独立地为氢、卤素、C1-4烷基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素、羟基、C1-4烷氧基、C1-4卤代烷氧基、C1-4烷硫基、C1-4卤代烷硫基、C1-4烷基氨基、二(C1-4)烷基氨基、C1-4烷氧基羰基和三(C1-4)烷基甲硅烷基]、C2-4链烯基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素]、C2-4炔基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素]、C3-7环烷基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素、C1-4烷基和C1-4卤代烷基]或三(C1-4)烷基甲硅烷基。
一方面,本发明提供了如上定义的式(I)化合物,其中Z是C1-4亚烷基[任选地被一个或多个取代基取代,每个取代基独立地选自羟基、氰基、C1-4烷氧基、C1-4卤代烷氧基、C1-4烷硫基、COOH和COO-C1-4烷基]。
一方面,本发明提供了如上定义的式(I)化合物,条件是:当X是0时,R7不是C2-6链烯基;R1是氢;R2、R3、R4和R5中的一个是氟,且其它的都是氢;n是1;且Het是
另一方面,本发明提供了如上定义的式(I)化合物,条件是:当X是0时,R7不是C2-6链烯基;R1、R2、R3、R4和R5都是氢;且Het是
另一方面,本发明提供了如上定义的式(I)化合物,条件是:当X是0时,R7不是C2-6链烯基;R1、R2、R3、R4和R5都是氢;n是1;且Het是
另一方面,本发明提供了如上定义的式(I)化合物,条件是:当X是0时,R7在4’位不是C2-6链烯基;R1、R3和R5都是氢;R2和R4各自独立地为氢或氟;n是0;或n是1;或n是2,且2个独立的R6取代基是在位置2′,3′或2′,5′或3′,5′;且Het是
卤素是氟、氯、溴或碘[优选氟、氯或溴]。
每个烷基部分是直链或支链,且是例如甲基、乙基、正丙基、正丁基、异丙基、正丁基、仲丁基、异丁基或叔丁基。类似地,每个亚烷基部分是直链或支链。
卤代烷基部分是被一个或多个相同的或不同的卤素原子取代的烷基部分,且是例如CF3、CF2Cl、CHF2、CH2F、CCl3、CF3CH2、CHF2CH2、CH2FCH2、CH3CHF或CH3CF2。
链烯基和炔基部分可以是直链或支链的形式。链烯基部分在合适时可以是(
E)-或(
Z)-构型。实例是乙烯基、烯丙基、乙炔基和炔丙基。
环烷基包括环丙基、环丁基、环戊基、环己基和环庚基。
在三(C1-4)烷基甲硅烷基和二(C1-4)烷基氨基中,每个烷基部分是独立地选择的。
在本说明书中,Me代表甲基,Et代表乙基。
优选地,Het是吡唑、吡咯、噻吩、呋喃、噻唑、异噻唑、噁唑、异噁唑、吡啶、吡嗪、嘧啶、哒嗪、5,6-二氢吡喃或5,6-二氢-1,4-氧硫杂环己二烯[更优选吡唑、吡咯、噻吩、呋喃、噻唑、噁唑、吡啶、嘧啶、哒嗪或5,6-二氢吡喃;更优选吡唑、吡咯、吡啶或噻唑;且更优选吡唑、吡咯或噻唑]。
一方面,优选地,Het是吡唑、吡咯、噻吩、呋喃、噻唑、异噻唑、噁唑、异噁唑、吡嗪、嘧啶、哒嗪、5,6-二氢吡喃或5,6-二氢-1,4-氧硫杂环己二烯[更优选吡唑、吡咯、噻吩、呋喃、噻唑、噁唑、嘧啶、哒嗪或5,6-二氢吡喃,且更优选吡唑、吡咯或噻唑]。
优选地,R1是氢、炔丙基、丙二烯基、甲酰基、COMe、COEt或COCH2OMe。
更优选地,R1是氢。
优选地,R2是氢。
优选地,R3是氢。
优选地,R4是氢。
优选地,R5是氢或卤素。
更优选地,R5是氢或氟。
更优选地,R5是氢。
在本发明的一个方面,R7是三(C1-4)烷基甲硅烷基。
优选地,Y1、Y2和Y3独立地是氢、卤素、C1-6烷基、C1-3卤代烷基、C1-4(卤代烷氧基)C1-4烷基、C1-4(卤代烷硫基)C1-4烷基、三甲基甲硅烷基、C2-4链烯基、C2-4卤代链烯基或C3-6环烷基(任选地被一个或多个取代基取代,每个取代基独立地选自卤素和C1-2烷基)。
优选地,Z是C1-2亚烷基[其可以任选地被一个或多个取代基取代,每个取代基独立地选自卤素、C1-4卤代烷基和C1-4卤代烷氧基]。
优选地,R7是在4’位。
优选地,R7是乙烯基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、C1-4烷基、C1-3卤代烷基、C3-6环烷基(任选地被1-5个取代基取代,每个取代基独立地选自卤素、CH3和C1-2卤代烷基)和三甲基甲硅烷基]、乙炔基[任选地被1个选自下述的取代基取代:环丙基、环戊基和环己基(每个任选地被1-5个取代基取代,每个取代基独立地选自卤素、CH3和C1-2卤代烷基)、卤素、C1-6烷基、C1-4卤代烷基、C2-4链烯基、C2-4卤代链烯基和三(C1-4)烷基甲硅烷基]、烯丙基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、CH3、C1-2卤代烷基和三甲基甲硅烷基]、炔丙基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、C1-4烷基、C1-2卤代烷基和三甲基甲硅烷基]或三(C1-4)烷基甲硅烷基。
在一个具体方面,R7优选地是乙烯基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、C1-4烷基、C1-3卤代烷基、C3-6环烷基和三甲基甲硅烷基]、乙炔基[任选地被一个选自下述的取代基取代:卤素、C1-4烷基、C1-2卤代烷基、环丙基(任选地被1-5个取代基取代,每个取代基独立地选自卤素、CH3、C1-2卤代烷基和三甲基甲硅烷基)和三甲基甲硅烷基]、烯丙基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、CH3、C1-2卤代烷基和三甲基甲硅烷基]、炔丙基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、CH3、C1-2卤代烷基和三甲基甲硅烷基]或三(C1-4)烷基甲硅烷基。
在另一个具体方面,R7优选地是乙烯基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、C1-4烷基、C1-3卤代烷基、C3-6环烷基和三甲基甲硅烷基]、乙炔基[任选地被一个选自下述的取代基取代:卤素、C1-4烷基、C1-2卤代烷基和三甲基甲硅烷基]、烯丙基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、CH3、C1-2卤代烷基和三甲基甲硅烷基]、炔丙基[任选地被1-3个取代基取代,每个取代基独立地选自卤素、CH3、C1-2卤代烷基和三甲基甲硅烷基]或三(C1-4)烷基甲硅烷基。
更优选地,R7是CH=CH2、CH=CH(CH3)、CH=CHSiMe3、CH=CF2、CH=CCl2、C(CH3)=CCl2、CH=CBr2、C(CH3)=CBr2、C(CH3)=CF2、CH=CFCl、CH=CFBr、C(CH3)=CFCl、C(CH3)=CFBr、CH=CFMe、CH=CBrMe、CH=CClMe、CH=CHBr、CH=CHF、CH=CHCl、CF=CF2、CCl=CF2、CCl=CH2、CBr=CH2、CF=CH2、C(CF3)=CFBr、C(CF3)=CFCl、C(CF3)=CBr2、C(CF3)=CCl2、C(CF3)=CF2、C(CF3)=CH2、CF=CHF、CH=CHCF3、CH=CFCF2Cl、CH=CClCF2Cl、CH=CBrCF2Cl、CH=C(CF3)2、CH=CHC2F5、CH=CHCF(CF3)2、C(CH3)=CHCF3、C(CH3)=CFCF3、C(CH3)=CClCF3、C(CH3)=CBrCF3、CH=CClCF3、CH=CClC2F5、CH=CBrCF3、CH=CFC2F5、CH=CFCF3、CH2CH=CH2、CH2CH=CF2、CH2CH=CCl2、CH2CH=CBr2、CH2CH=CFBr、CH2CH=CFCl、CH2CH=CClCF3、CH2CH=CHSiMe3、C≡CH、C≡CSiMe3、C≡CSiEt3、C≡CSiMe2C(CH3)3、C≡CCl、C≡CBr、C≡CF、C≡CCF3、C≡CCF2H、C≡CCF2Cl、C≡CCF2Me、C≡CCF2Et、C≡CCHFCl、C≡CCF2Br、C≡CC2F5、C≡CCF(CF3)2、C≡CCHF(CF3)、C≡CCH2F、C≡CCH(Me)F、C≡CCH(Et)F、C≡CMe、C≡CCH2Me、C≡CCHMe2、C≡CCH2CHMe2、C≡CCMe3、C≡CCH2CMe3、C≡CCH2SiMe3、C≡CCMe2Cl、C≡CCMe2F、C≡CCH2OMe、C≡CCH2CF3、C≡CCMe2OMe、C≡CCMe2OH、C≡CCMe2OCOMe、C≡CC(Me)=CH2、C≡CCF=CF2、C≡C(环丙基)、C≡C(环戊基)、C≡C(1-F-环戊基)、CH2C≡CH、CF2C≡CH、CHFC≡CH、CH(CF3)C≡CH、SiMe3、CH2C≡CCMe3或CH2C≡CSiMe3。
在一个具体方面,R7更优选地是CH=CH2、CH=CH(CH3)、CH=CHSiMe3、CH=CF2、CH=CCl2、C(CH3)=CCl2、CH=CBr2、CF=CF2、CCl=CH2、CBr=CH2、CF=CH2、CF=CHF、CH=CHCF3、CH=CClCF3、CH=CBrCF3、CH2CH=CH2、CH2CH=CHSiMe3、C≡CH、C≡CSiMe3、C≡CSiEt3、C≡CSiMe2C(CH3)3、C≡CCl、C≡CBr、C≡CCF3、C≡CCF2H、C≡CCF2Cl、C≡CCF2Br、C≡CCF(CF3)2C≡CMe、C≡CCHMe2、C≡CCMe3、C≡CCMe2Cl、C≡CCH2OMe、C≡C(环C3H5)、C≡C(环C5H9)、CH2C≡CH、SiMe3或CH2C≡CSiMe3。
更优选地,R7是CH=CF2、CH=CCl2、C(CH3)=CCl2、CH=CBr2、C(CH3)=CBr2、C(CH3)=CF2、CH=CFCl、CH=CFBr、C(CH3)=CFCl、C(CH3)=CFBr、CH=CHBr、CH=CHF、CH=CHCl、CCl=CH2、CH=CHCF3、CH=CFCF2Cl、CH=CClCF2Cl、CH=CBrCF2Cl、CH=C(CF3)2、CH=CHC2F5、CH=CHCF(CF3)2、C(CH3)=CHCF3、CH=CClCF3、CH=CClC2F5、CH=CFC2F5、CH=CBrCF3、CH=CFCF3、CH2CH=CClCF3、CH2CH=CCl2、CH2CH=CBr2、C≡CH、C≡CSiMe3、C≡CSiEt3、C≡CSiMe2C(CH3)3、C≡CCl、C≡CCF3、C≡CCF2H、C≡CCF2Cl、C≡CCHFCl、C≡CCF2Me、C≡CCF2Et、C≡CCHFEt、C≡CCF2Br、C≡CCF(CF3)2、C≡CCF2CF3、C≡CCHF(CF3)、C≡CCH2F、C≡CCH(Me)F、C≡CMe、C≡CCHMe2、C≡CCH2Me、C≡CCH2CHMe2、C≡CCMe3、C≡CCH2CMe3、C≡CCMe2F、C≡CCH2CF3、C≡C(环丙基)、C≡C(环戊基)、C≡C(1-F-环戊基)、C≡CC(Me)=CH2、C≡CCF=CF2、C≡CCH2SiMe3、CH2C≡CH、CF2C≡CH或CHFC≡CH。
在一个具体方面,R7更优选地是CH=CH2、CH=CHSiMe3、CH=CF2、CH=CCl2、CH=CBr2、CF=CF2、CCl=CH2、CBr=CH2、CF=CHF、CH=CHCF3、CH=CClCF3、C≡CH、C≡CSiMe3、C≡CCl、C≡CBr、C≡CCF3、C≡CMe、C≡CCMe3、C≡CCHMe2、C≡C(环C3H5)、CH2C≡CH、SiMe3或CH2C≡CSiMe3。
更优选地,R7是CH=CF2、CH=CCl2、CH=CBr2、CH=CFCl、CH=CFBr、CH=CHBr、CH=CHF、CH=CHCl、CCl=CH2、CH=CHCF3、CH=CFCF2Cl、CH=CClCF2Cl、CH=CBrCF2Cl、CH=C(CF3)2、CH=CHC2F5、CH=CClCF3、CH=CBrCF3、CH=CFCF3、C≡CH、C≡CSiMe3、C≡CCl、C≡CCF3、C≡CCF2H、C≡CCHFCl、C≡CCHF(CF3)、C≡CCF2Cl、C≡CCF2Me、C≡CCF2Br、C≡CCF2CF3、C≡CCH2F、C≡CCH(Me)F、C≡CMe、C≡CCHMe2、C≡CCH2CHMe2、C≡CCMe3、C≡CCCH2CMe3、C≡CCMe2F、C≡CCH2CF3、C≡C(环丙基)、C≡C(环戊基)、C≡C(1-F-环戊基)、CH2C≡CH、CF2C≡CH、CHFC≡CH或C≡CCH2Me。
在一个具体方面,R7更优选地是CH=CHSiMe3、CH=CF2、CH=CCl2、CH=CBr2、CF=CF2、CCl=CH2、CBr=CH2、CF=CHF、CH=CHCF3、CH=CClCF3、C≡CH、C≡CSiMe3、C≡CCl、C≡CBr、C≡CCF3、C≡CMe、C≡CCMe3、C≡CCHMe2、C≡C(环C3H5)、CH2C≡CH、SiMe3或CH2C≡CSiMe3。
优选地,Het环中的氮原子独立地是未取代的或被Ry取代的。
当Ry是氮原子上的取代基时,它优选地是C1-3烷基、C1-3卤代烷基或甲氧基亚甲基;更优选C1-2烷基、CF3、CF2Cl、CHF2、CH2F或甲氧基亚甲基;更优选甲基、CHF2或甲氧基亚甲基;更优选甲基或甲氧基亚甲基;最优选甲基。
优选地,未结合到被CXNR1取代的原子上的Het环中的碳原子独立地是未取代的或被Ry取代的。
当Ry是未结合到被CXNR1取代的原子上的碳原子上的取代基时,它优选地是卤素、C1-3烷基、C1-3卤代烷基或甲氧基亚甲基;更优选氯、甲氧基亚甲基、CH3、CHF2或CF3;更优选氯、CH3、CHF2或CF3;更优选CH3或CF3。结合到被CXNR1取代的原子上的Het环中可以有1或2个碳原子;优选地,这样的碳原子独立地是未取代的或被Ry取代的。
当Ry是结合到被CXNR1取代的原子上的碳原子上的取代基时,它优选地是卤素、C1-3烷基或C1-3卤代烷基;更优选氯、氟、溴、C1-2烷基、CF3、CF2Cl、CHF2、CH2F;且更优选氯、氟、溴、甲基、CF3、CHF2或CH2F。
更优选地,当结合到被CXNR1取代的原子上的Het环中仅有1个碳原子时,该碳原子是被Ry取代的。
更优选地,当结合到被CXNR1取代的原子上的Het环中有2个碳原子时,一个这样的碳原子是被Ry取代的,另一个碳原子是未取代的或被氟、氯或甲基取代的。
优选地,m是0。
优选地,n是0。
优选地,X是0。
式(II)化合物:
其中R1、R2、R3、R4、R5、R6、R7和n如上面对式(I)化合物所定义的,也是新的[除其中R1、R2、R3、R4和R5各自是氢,n是0且R7是CH=CHCH2CO2H的式(II)化合物以外],且用作制备式(I)化合物的中间体。
因此,一方面,本发明提供了式(II)化合物,其中R1、R2、R3、R4、R5、R6、R7和n是如上面对式(I)化合物所定义的,条件是:当R1、R2、R3、R4和R5各自是氢且n是0时,R7不是CH=CHCH2CO2H。
式(II)化合物中的R1、R2、R3、R4、R5、R6、R7和n的优选值是如上面对式(I)化合物所定义的。
许多式(III)化合物:
其中R2、R3、R4、R5、R6、R7和n是如上面对式(I)化合物所定义的,且Hal是溴、氯或碘,也是新的,且用作制备式(I)化合物的中间体。
某些式(III)化合物是已知的;表0显示了已知的式(IIIa)化合物,其中Hal、R2、R3、R4和R7是如表0中所定义的。
表0
Hal | R2 | R3 | R4 | R7 |
Cl | Cl | H | H | C(CH3)=CH-CH2-OH |
Br | H | Me | H | C(CF3)=CF2 |
Br | H | Me | Br | C(CF3)=CF2 |
Cl | H | H | H | C::CH |
Cl | H | H | H | CH=CH-CH2-CH2-OH |
Cl | H | H | H | C(CH3)=CH-CH2-OH |
Cl | H | H | H | C(CH3)=CH-C(=O)-OC2H5 |
Cl | H | H | H | C(CH3)=CH-CH(OH)CH3 |
Cl | H | H | H | CH=CH-CH(OH)CH3 |
因此,在另一方面,本发明提供了式(III)化合物,其中R2、R3、R4、R5、R6、R7和n是如上面对式(I)化合物所定义的,且Hal是溴、氯或碘;条件是:该化合物不是根据表0的式(IIIa)化合物。
式(III)化合物中的R2、R3、R4、R5、R6、R7和n的优选值是如上面对式(I)化合物所定义的。
优选地,Hal是溴或氯。
更优选地,Hal是溴。
式(I)、(II)和(III)化合物可以作为不同的几何或光学异构体、或以不同的互变异构形式存在。对于每个通式,本发明包括了所有这样的异构体、互变异构体、其所有比例的混合物和同位素形式,例如氘化的化合物。
下面表1-13中的化合物解释了本发明的化合物。
表1
化合物编号 | R1 | R7 | R8 | R9 | R10 | X |
1.01 | H | C::CH | H | Me | CF3 | O |
1.02 | H | C::CH | H | Me | CF3 | S |
1.03 | H | C::CH | H | Me | CF2H | O |
1.04 | 炔丙基 | C::CH | H | Me | CF3 | O |
1.05 | H | C::CH | F | Me | Me | O |
1.06 | H | C::CH | H | CH2OMe | CF3 | O |
1.07 | 丙二烯基 | C::CH | H | Me | CF3 | O |
1.08 | H | C::CSiMe3 | H | Me | CF3 | O |
1.09 | H | C::CSiMe3 | H | Me | CF3 | S |
1.10 | H | C::CSiMe3 | H | Me | CF2H | O |
1.11 | H | C::CSiMe3 | F | Me | Me | O |
1.12 | H | C::CCl | H | Me | CF3 | O |
1.13 | H | C::CCl | H | Me | CF2H | O |
1.14 | H | C::CCl | F | Me | Me | O |
1.15 | H | C::CBr | H | Me | CF3 | O |
1.16 | H | C::CBr | H | Me | CF2H | O |
1.17 | H | C::CBr | F | Me | Me | O |
1.18 | H | C::CCF3 | H | Me | CF3 | O |
1.19 | H | C::CCF3 | H | Me | CF2H | O |
1.20 | H | C::CCF3 | F | Me | Me | O |
1.21 | 丙二烯基 | C::CCF3 | H | Me | CF3 | O |
1.22 | H | CH=CH2 | H | Me | CF3 | O |
1.23 | H | CH=CH2 | H | Me | CF3 | S |
1.24 | H | CH=CH2 | H | Me | CF2H | O |
1.25 | 炔丙基 | CH=CH2 | H | Me | CF3 | O |
1.26 | H | CH=CH2 | F | Me | Me | O |
1.27 | H | CH=CH2 | H | CH2OMe | CF3 | O |
1.28 | 丙二烯基 | CH=CH2 | H | Me | CF3 | O |
1.29 | H | CH=CF2 | H | Me | CF3 | O |
1.30 | H | CH=CF2 | H | Me | CF2H | O |
1.31 | H | CH=CF2 | F | Me | Me | O |
1.32 | H | CH=CCl2 | H | Me | CF3 | O |
1.33 | H | CH=CCl2 | H | Me | CF2H | O |
1.34 | H | CH=CCl2 | F | Me | Me | O |
1.35 | H | CH=CBr2 | H | Me | CF3 | O |
1.36 | H | CH=CBr2 | H | Me | CF2H | O |
1.37 | H | CH=CBr2 | F | Me | Me | O |
1.38 | H | CF=CF2 | H | Me | CF3 | O |
1.39 | H | CF=CF2 | H | Me | CF2H | O |
1.40 | H | CF=CF2 | F | Me | Me | O |
1.41 | H | CCl=CH2 | H | Me | CF3 | O |
1.42 | H | CCl=CH2 | H | Me | CF2H | O |
1.43 | H | CCl=CH2 | F | Me | Me | O |
1.44 | H | CBr=CH2 | H | Me | CF3 | O |
1.45 | H | CBr=CH2 | H | Me | CF2H | O |
1.46 | H | CBr=CH2 | F | Me | Me | O |
1.47 | H | CF=CHF | H | Me | CF3 | O |
1.48 | H | CF=CHF | H | Me | CF2H | O |
1.49 | H | CF=CHF | F | Me | Me | O |
1.50 | H | CH=CHSiMe3 | H | Me | CF3 | O |
1.51 | H | CH=CHSiMe3 | H | Me | CF2H | O |
1.52 | H | CH=CHSiMe3 | F | Me | Me | O |
1.53 | H | CH=CHCF3 | H | Me | CF3 | O |
1.54 | H | CH=CHCF3 | H | Me | CF2H | O |
1.55 | H | CH=CHCF3 | F | Me | Me | O |
1.56 | H | CH=CClCF3 | H | Me | CF3 | O |
1.57 | H | CH=CClCF3 | H | Me | CF2H | O |
1.58 | H | CH=CClCF3 | F | Me | Me | O |
1.59 | H | CH2C::CH | H | Me | CF3 | O |
1.60 | H | CH2C::CH | H | Me | CF2H | O |
1.61 | H | CH2C::CH | F | Me | Me | O |
1.62 | H | CH2C::CH | H | CH2OMe | CF3 | O |
1.63 | H | CH2C::CSiMe3 | H | Me | CF3 | O |
1.64 | H | CH2C::CSiMe3 | H | Me | CF2H | O |
1.65 | H | CH2C::CSiMe3 | F | Me | Me | O |
1.66 | H | C::CCMe3 | H | Me | CF3 | O |
1.67 | H | C::CCMe3 | H | Me | CF2H | O |
1.68 | H | C::CCMe3 | F | Me | Me | O |
1.69 | H | C::CMe | H | Me | CF3 | O |
1.70 | H | C::CMe | H | Me | CF2H | O |
1.71 | H | C::CMe | F | Me | Me | O |
1.72 | COMe | C::CH | H | Me | CF3 | O |
1.73 | H | C::CH | H | CF2H | CF2H | O |
1.74 | H | C::CH | H | CF2H | CF3 | O |
1.75 | H | C::CH | H | Me | CH2F | O |
1.76 | H | C::CSiMe3 | H | Me | CH2F | O |
1.77 | H | C::C(环丙基) | H | Me | CF3 | O |
1.78 | H | C::C(环丙基) | H | Me | CHF2 | O |
1.79 | H | SiMe3 | H | Me | CH2F | O |
1.80 | H | SiMe3 | H | Me | CF3 | O |
1.81 | H | SiMe3 | H | Me | CHF2 | O |
1.82 | H | C::CF | H | Me | CF3 | O |
1.83 | H | C::CF | H | Me | CF2H | O |
1.84 | H | C::CF | F | Me | Me | O |
1.85 | H | C::CCF2Cl | H | Me | CF3 | O |
1.86 | H | C::CCF2Cl | H | Me | CF2H | O |
1.87 | H | C::CCF2Cl | F | Me | Me | O |
1.88 | H | C::CCF2H | H | Me | CF3 | O |
1.89 | H | C::CCF2H | H | Me | CF2H | O |
1.90 | H | C::CCF2H | F | Me | Me | O |
1.91 | H | C::CCF2Br | H | Me | CF3 | O |
1.92 | H | C::CCF2Br | H | Me | CF2H | O |
1.93 | H | C::CCF2Br | F | Me | Me | O |
1.94 | H | C::CCH2F | H | Me | CF3 | O |
1.95 | H | C::CCH2F | H | Me | CF2H | O |
1.96 | H | C::CCH2F | F | Me | Me | O |
1.97 | H | C::CCH(Me)F | H | Me | CF3 | O |
1.98 | H | C::CCH(Me)F | H | Me | CF2H | O |
1.99 | H | C::CCH(Me)F | F | Me | Me | O |
1.100 | H | C::CC(Me)2F | H | Me | CF3 | O |
1.101 | H | C::CC(Me)2F | H | Me | CF2H | O |
1.102 | H | C::CC(Me)2F | F | Me | Me | O |
1.103 | H | C::CCH2C(Me)3 | H | Me | CF3 | O |
1.104 | H | C::CCH2C(Me)3 | H | Me | CF2H | O |
1.105 | H | C::CCH2C(Me)3 | F | Me | Me | O |
1.106 | H | C::CCH(Me)2 | H | Me | CF3 | O |
1.107 | H | C::CCH(Me)2 | H | Me | CF2H | O |
1.108 | H | C::CCH(Me)2 | F | Me | Me | O |
1.109 | H | C::CCH2CH(Me)2 | H | Me | CF3 | O |
1.110 | H | C::CCH2CH(Me)2 | H | Me | CF2H | O |
1.111 | H | C::CCH2CH(Me)2 | F | Me | Me | O |
1.112 | H | CH2C::CCMe3 | H | Me | CF3 | O |
1.113 | H | CH2C::CCMe3 | H | Me | CF2H | O |
1.114 | H | CH2C::CCMe3 | F | Me | Me | O |
1.115 | H | CF2C::CCMe3 | H | Me | CF3 | O |
1.116 | H | CF2C::CCMe3 | H | Me | CF2H | O |
1.117 | H | CF2C::CCMe3 | F | Me | Me | O |
1.118 | H | CF2C::CMe | H | Me | CF3 | O |
1.119 | H | CF2C::CMe | H | Me | CF2H | O |
1.120 | H | CF2C::CMe | F | Me | Me | O |
1.121 | H | CF2C::CH | H | Me | CF3 | O |
1.122 | H | CF2C::CH | H | Me | CF2H | O |
1.123 | H | CF2C::CH | F | Me | Me | O |
1.124 | H | CMe2C::CH | H | Me | CF3 | O |
1,125 | H | CMe2C::CH | H | Me | CF2H | O |
1.126 | H | CMe2C::CH | F | Me | Me | O |
1.127 | H | CHFC::CH | H | Me | CF3 | O |
1.128 | H | CHFC::CH | H | Me | CF2H | O |
1.129 | H | CHFC::CH | F | Me | Me | O |
1.130 | H | CHMeC::CH | H | Me | CF3 | O |
1.131 | H | CHMeC::CH | H | Me | CF2H | O |
1.132 | H | CHMeC::CH | F | Me | Me | O |
1.133 | H | CH(CF3)C::CH | H | Me | CF3 | O |
1.134 | H | CH(CF3)C::CH | H | Me | CF2H | O |
1.135 | H | CH(CF3)C::CH | F | Me | Me | O |
1.136 | H | C::C(1-F-环戊基) | H | Me | CF3 | O |
1.137 | H | C::C(1-F-环戊基) | H | Me | CHF2 | O |
1.138 | H | C::CCH2OMe | H | Me | CF3 | O |
1.139 | H | C::CCH2OMe | H | Me | CF2H | O |
1.140 | H | C::CCH2OMe | F | Me | Me | O |
1.141 | H | C::CCMe2OMe | H | Me | CF3 | O |
1.142 | H | C::CCMe2OMe | H | Me | CF2H | O |
1.143 | H | C::CCMe2OMe | F | Me | Me | O |
1.144 | H | C::CCMe2OCOMe | H | Me | CF3 | O |
1.145 | H | C::CCMe2OCOMe | H | Me | CF2H | O |
1.146 | H | C::CCF2Me | H | Me | CF3 | O |
1.147 | H | C::CCF2Me | H | Me | CF2H | O |
1.148 | H | C::CCF2Me | F | Me | Me | O |
1.149 | H | C::CC(Me)=CH2 | H | Me | CF3 | O |
1.150 | H | C::CC(Me)=CH2 | H | Me | CF2H | O |
1.151 | H | CH=CFCl | H | Me | CF3 | O |
1.152 | H | CH=CFCl | H | Me | CF2H | O |
1.153 | H | CH=CFCl | F | Me | Me | O |
1.154 | H | CH=CFBr | H | Me | CF3 | O |
1.155 | H | CH=CFBr | H | Me | CF2H | O |
1.156 | H | CH=CFBr | F | Me | Me | O |
1.157 | H | CH=CHBr | H | Me | CF3 | O |
1.158 | H | CH=CHBr | H | Me | CF2H | O |
1.159 | H | CH=CHBr | F | Me | Me | O |
1.160 | H | CH=CHF | H | Me | CF3 | O |
1.161 | H | CH=CHF | H | Me | CF2H | O |
1.162 | H | CH=CHF | F | Me | Me | O |
1.163 | H | CMe=CHCF3 | H | Me | CF3 | O |
1.164 | H | CMe=CHCF3 | H | Me | CF2H | O |
1.165 | H | CMe=CHCF3 | F | Me | Me | O |
1.166 | H | CH=CFCF3 | H | Me | CF3 | O |
1.167 | H | CH=CFCF3 | H | Me | CF2H | O |
1.168 | H | CH=CFCF3 | F | Me | Me | O |
1.169 | H | CH=CBrCF3 | H | Me | CF3 | O |
1.170 | H | CH=CBrCF3 | H | Me | CF2H | O |
1.171 | H | CH=CBrCF3 | F | Me | Me | O |
1.172 | H | CH=CHC2F5 | H | Me | CF3 | O |
1.173 | H | CH=CHC2F5 | H | Me | CF2H | O |
1.174 | H | CH=CHC2F5 | F | Me | Me | O |
1.175 | H | CH=CHCl | H | Me | CF3 | O |
1.176 | H | CH=CHCl | H | Me | CF2H | O |
1.177 | H | CH=CHCl | F | Me | Me | O |
1.178 | H | CH=C(CF3)2 | H | Me | CF3 | O |
1.179 | H | CH=C(CF3)2 | H | Me | CF2H | O |
1.180 | H | CH=C(CF3)2 | F | Me | Me | O |
1.181 | H | CMe=CFCl | H | Me | CF3 | O |
1.182 | H | CMe=CFCl | H | Me | CF2H | O |
1.183 | H | CMe=CFCl | F | Me | Me | O |
1.184 | H | CMe=CFBr | H | Me | CF3 | O |
1.185 | H | CMe=CFBr | H | Me | CF2H | O |
1.186 | H | CMe=CFBr | F | Me | Me | O |
1.187 | H | CMe=CF2 | H | Me | CF3 | O |
1.188 | H | CMe=CF2 | H | Me | CF2H | O |
1.189 | H | CMe=CF2 | F | Me | Me | O |
1.190 | H | CMe=CCl2 | H | Me | CF3 | O |
1.191 | H | CMe=CCl2 | H | Me | CF2H | O |
1.192 | H | CMe=CCl2 | F | Me | Me | O |
1.193 | H | CMe=CBr2 | H | Me | CF3 | O |
1.194 | H | CMe=CBr2 | H | Me | CF2H | O |
1.195 | H | CMe=CBr2 | F | Me | Me | O |
1.196 | H | CMe=CFCF3 | H | Me | CF3 | O |
1.197 | H | CMe=CFCF3 | H | Me | CF2H | O |
1.198 | H | CMe=CFCF3 | F | Me | Me | O |
1.199 | H | CMe=CClCF3 | H | Me | CF3 | O |
1.200 | H | CMe=CClCF3 | H | Me | CF2H | O |
1.201 | H | CMe=CClCF3 | F | Me | Me | O |
1.202 | H | CCF3=CF2 | H | Me | CF3 | O |
1.203 | H | CCF3=CF2 | H | Me | CF2H | O |
1.204 | H | CCF3=CF2 | F | Me | Me | O |
1.205 | H | CCF3=CCl2 | H | Me | CF3 | O |
1.206 | H | CCF3=CCl2 | H | Me | CF2H | O |
1.207 | H | CCF3=CCl2 | F | Me | Me | O |
1.208 | H | CCF3=CBr2 | H | Me | CF3 | O |
1.209 | H | CCF3=CBr2 | H | Me | CF2H | O |
1.210 | H | CCF3=CBr2 | F | Me | Me | O |
1.211 | H | CCF3=CH2 | H | Me | CF3 | O |
1.212 | H | CCF3=CH2 | H | Me | CF2H | O |
1.213 | H | CCF3=CH2 | F | Me | Me | O |
1.214 | H | CCF3=CFBr | H | Me | CF3 | O |
1.215 | H | CCF3=CFBr | H | Me | CF2H | O |
1.216 | H | CCF3=CFBr | F | Me | Me | O |
1.217 | H | CCF3=CHF | H | Me | CF3 | O |
1.218 | H | CCF3=CHF | H | Me | CF2H | O |
1.219 | H | CCF3=CHF | F | Me | Me | O |
1.220 | H | CCF3=CFCl | H | Me | CF3 | O |
1.221 | H | CCF3=CFCl | H | Me | CF2H | O |
1.222 | H | CCF3=CFCl | F | Me | Me | O |
1.223 | H | CCF3=CHCl | H | Me | CF3 | O |
1.224 | H | CCF3=CHCl | H | Me | CF2H | O |
1.225 | H | CCF3=CHCl | F | Me | Me | O |
1.226 | H | CH=CFCF2Cl | H | Me | CF3 | O |
1.227 | H | CH=CFCF2Cl | H | Me | CF2H | O |
1.228 | H | CH=CFCF2Cl | F | Me | Me | O |
1.229 | H | CH=CClCF2Cl | H | Me | CF3 | O |
1.230 | H | CH=CClCF2Cl | H | Me | CF2H | O |
1.231 | H | CH=CClCF2Cl | F | Me | Me | O |
1.232 | H | CH2CF=CF2 | H | Me | CF3 | O |
1.233 | H | CH2CF=CF2 | H | Me | CF2H | O |
1.234 | H | CH2CF=CF2 | F | Me | Me | O |
1.235 | H | CF=CFBr | H | Me | CF3 | O |
1.236 | H | CF=CFBr | H | Me | CF2H | O |
1.237 | H | CF=CFBr | F | Me | Me | O |
1.238 | H | CH2CH=CF2 | H | Me | CF3 | O |
1.239 | H | CH2CH=CF2 | H | Me | CF2H | O |
1.240 | H | CH2CH=CF2 | F | Me | Me | O |
1.241 | H | CH2CH=CCl2 | H | Me | CF3 | O |
1.242 | H | CH2CH=CCl2 | H | Me | CF2H | O |
1.243 | H | CH2CH=CCl2 | F | Me | Me | O |
1.244 | H | CH2CH=CBr2 | H | Me | CF3 | O |
1.245 | H | CH2CH=CBr2 | H | Me | CF2H | O |
1.246 | H | CH2CH=CBr2 | F | Me | Me | O |
1.247 | H | CCl=CF2 | H | Me | CF3 | O |
1.248 | H | CCl=CF2 | H | Me | CF2H | O |
1.249 | H | CCl=CF2 | F | Me | Me | O |
1.250 | H | C::CCMe2OH | H | Me | CF3 | O |
1.251 | H | C::CCMe2OH | H | Me | CF2H | O |
1.252 | H | C::CSi(Me2)CMe3 | H | Me | CF3 | O |
1.253 | H | C::CSi(Me2)CMe3 | H | Me | CF2H | O |
1.254 | H | C::CCH2SiMe3 | H | Me | CF3 | O |
1.255 | H | C::CCH2SiMe3 | H | Me | CF2H | O |
1.256 | H | C::CCH2SiMe3 | F | Me | Me | O |
1.257 | H | C::CCMe3 | H | CF2H | CF3 | O |
1.258 | H | C::CCH2CF3 | H | Me | CF3 | O |
1.259 | H | C::CCH2CF3 | H | Me | CF2H | O |
1.260 | H | C::CCH2CF3 | F | Me | Me | O |
1.261 | H | C::CCMe3 | H | CF2H | CF2H | O |
1.262 | H | C::CCH2CH3 | H | Me | CF3 | O |
1.263 | H | C::CCH2CH3 | H | Me | CF2H | O |
1.264 | H | C::CCH2CH3 | F | Me | Me | O |
1.265 | H | C::CCF=CF2 | H | Me | CF3 | O |
1.266 | H | C::CCF=CF2 | H | Me | CF2H | O |
1.267 | H | C::CCHFCl | H | Me | CF3 | O |
1.268 | H | C::CCHFCl | H | Me | CF2H | O |
1.269 | H | C::CCHFCl | F | Me | Me | O |
1.270 | H | CH=CFC2F5 | H | Me | CF3 | O |
1.271 | H | CH=CFC2F5 | H | Me | CF2H | O |
1.272 | H | CH=CFC2F5 | F | Me | Me | O |
1.273 | H | C::CCF2CH2CH3 | H | Me | CF3 | O |
1.274 | H | C::CCF2CH2CH3 | H | Me | CF2H | O |
1.275 | H | C::CCF2CH2CH3 | F | Me | Me | O |
1.276 | H | C::CCHFCH2CH3 | H | Me | CF3 | O |
1.277 | H | C::CCHFCH2CH3 | H | Me | CF2H | O |
1.278 | H | C::CCHFCH2CH3 | F | Me | Me | O |
1.279 | H | C::CCF(CF3)2 | H | Me | CF3 | O |
1.280 | H | C::CCF(CF3)2 | H | Me | CF2H | O |
1.281 | H | C::CCF(CF3)2 | F | Me | Me | O |
1.282 | H | CH=CClC2F5 | H | Me | CF3 | O |
1.283 | H | CH=CClC2F5 | H | Me | CF2H | O |
1.284 | H | CH=CClC2F5 | F | Me | Me | O |
1.285 | H | C::CC2F5 | H | Me | CF3 | O |
1.286 | H | C::CC2F5 | H | Me | CF2H | O |
1.287 | H | C::CC2F5 | F | Me | Me | O |
表1提供了287种式(Ia)化合物:
其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种式(IaA)化合物:
其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种化合物式(IaB),其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种式(IaC)化合物,其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种式(IaD)化合物,其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种式(IaE)化合物,其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种式(IaF)化合物,其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种式(IaG)化合物,其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种式(IaH)化合物,其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种化合物式(IaI)其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表1提供了287种式(IaJ)化合物,其中R1、R7、R8、R9、R10和X是如表1中所定义的。
表2
化合物编号 | R1 | R7 | R8 | R9 | R10 | X |
2.01 | H | C::CH | H | Me | CF3 | O |
2.02 | H | C::CH | H | Me | CF3 | S |
2.03 | H | C::CH | H | Me | CF2H | O |
2.04 | 炔丙基 | C::CH | H | Me | CF3 | O |
2.05 | H | C::CH | F | Me | Me | O |
2.06 | H | C::CH | H | CH2OMe | CF3 | O |
2.07 | 丙二烯基 | C::CH | H | Me | CF3 | O |
2.08 | H | C::CSiMe3 | H | Me | CF3 | O |
2.09 | H | C::CSiMe3 | H | Me | CF3 | S |
2.10 | H | C::CSiMe3 | H | Me | CF2H | O |
2.11 | H | C::CSiMe3 | F | Me | Me | O |
2.12 | H | C::CCl | H | Me | CF3 | O |
2.13 | H | C::CCl | H | Me | CF2H | O |
2.14 | H | C::CCl | F | Me | Me | O |
2.15 | H | C::CBr | H | Me | CF3 | O |
2.16 | H | C::CBr | H | Me | CF2H | O |
2.17 | H | C::CBr | F | Me | Me | O |
2.18 | H | C::CCF3 | H | Me | CF3 | O |
2.19 | H | C::CCF3 | H | Me | CF2H | O |
2.20 | H | C::CCF3 | F | Me | Me | O |
2.21 | 丙二烯基 | C::CCF3 | H | Me | CF3 | O |
2.22 | H | CH=CH2 | H | Me | CF3 | O |
2.23 | H | CH=CH2 | H | Me | CF3 | S |
2.24 | H | CH=CH2 | H | Me | CF2H | O |
2.25 | 炔丙基 | CH=CH2 | H | Me | CF3 | O |
2.26 | H | CH=CH2 | F | Me | Me | O |
2.27 | H | CH=CH2 | H | CH2OMe | CF3 | O |
2.28 | 丙二烯基 | CH=CH2 | H | Me | CF3 | O |
2.29 | H | CH=CF2 | H | Me | CF3 | O |
2.30 | H | CH=CF2 | H | Me | CF2H | O |
2.31 | H | CH=CF2 | F | Me | Me | O |
2.32 | H | CH=CCl2 | H | Me | CF3 | O |
2.33 | H | CH=CCl2 | H | Me | CF2H | O |
2.34 | H | CH=CCl2 | F | Me | Me | O |
2.35 | H | CH=CBr2 | H | Me | CF3 | O |
2.36 | H | CH=CBr2 | H | Me | CF2H | O |
2.37 | H | CH=CBr2 | F | Me | Me | O |
2.38 | H | CF=CF2 | H | Me | CF3 | O |
2.39 | H | CF=CF2 | H | Me | CF2H | O |
2.40 | H | CF=CF2 | F | Me | Me | O |
2.41 | H | CCl=CH2 | H | Me | CF3 | O |
2.42 | H | CCl=CH2 | H | Me | CF2H | O |
2.43 | H | CCl=CH2 | F | Me | Me | O |
2.44 | H | CBr=CH2 | H | Me | CF3 | O |
2.45 | H | CBr=CH2 | H | Me | CF2H | O |
2.46 | H | CBr=CH2 | F | Me | Me | O |
2.47 | H | CF=CHF | H | Me | CF3 | O |
2.48 | H | CF=CHF | H | Me | CF2H | O |
2.49 | H | CF=CHF | F | Me | Me | O |
2.50 | H | CH=CHSiMe3 | H | Me | CF3 | O |
2.51 | H | CH=CHSiMe3 | H | Me | CF2H | O |
2.52 | H | CH=CHSiMe3 | F | Me | Me | O |
2.53 | H | CH=CHCF3 | H | Me | CF3 | O |
2.54 | H | CH=CHCF3 | H | Me | CF2H | O |
2.55 | H | CH=CHCF3 | F | Me | Me | O |
2.56 | H | CH=CClCF3 | H | Me | CF3 | O |
2.57 | H | CH=CClCF3 | H | Me | CF2H | O |
2.58 | H | CH=CClCF3 | F | Me | Me | O |
2.59 | H | CH2C::CH | H | Me | CF3 | O |
2.60 | H | CH2C::CH | H | Me | CF2H | O |
2.61 | H | CH2C::CH | F | Me | Me | O |
2.62 | H | CH2C::CH | H | CH2OMe | CF3 | O |
2.63 | H | CH2C::CSiMe3 | H | Me | CF3 | O |
2.64 | H | CH2C::CSiMe3 | H | Me | CF2H | O |
2.65 | H | CH2C::CSiMe3 | F | Me | Me | O |
2.66 | H | C::CCMe3 | H | Me | CF3 | O |
2.67 | H | C::CCMe3 | H | Me | CF2H | O |
2.68 | H | C::CCMe3 | F | Me | Me | O |
2.69 | H | C::CMe | H | Me | CF3 | O |
2.70 | H | C::CMe | H | Me | CF2H | O |
2.71 | H | C::CMe | F | Me | Me | O |
2.72 | COMe | C::CH | H | Me | CF3 | O |
2.73 | H | C::CH | H | CF2H | CF2H | O |
2.74 | H | C::CH | H | CF2H | CF3 | O |
2.75 | H | C::CH | H | Me | CH2F | O |
2.76 | H | C::CSiMe3 | H | Me | CH2F | O |
2.77 | H | C::C(环丙基) | H | Me | CF3 | O |
2.78 | H | C::C(环丙基) | H | Me | CHF2 | O |
2.79 | H | SiMe3 | H | Me | CH2F | O |
2.80 | H | SiMe3 | H | Me | CF3 | O |
2.81 | H | SiMe3 | H | Me | CHF2 | O |
2.82 | H | C::CF | H | Me | CF3 | O |
2.83 | H | C::CF | H | Me | CF2H | O |
2.84 | H | C::CF | F | Me | Me | O |
2.85 | H | C::CCF2Cl | H | Me | CF3 | O |
2.86 | H | C::CCF2Cl | H | Me | CF2H | O |
2.87 | H | C::CCF2Cl | F | Me | Me | O |
2.88 | H | C::CCF2H | H | Me | CF3 | O |
2.89 | H | C::CCF2H | H | Me | CF2H | O |
2.90 | H | C::CCF2H | F | Me | Me | O |
2.91 | H | C::CCF2Br | H | Me | CF3 | O |
2.92 | H | C::CCF2Br | H | Me | CF2H | O |
2.93 | H | C::CCF2Br | F | Me | Me | O |
2.94 | H | C::CCH2F | H | Me | CF3 | O |
2.95 | H | C::CCH2F | H | Me | CF2H | O |
2.96 | H | C::CCH2F | F | Me | Me | O |
2.97 | H | C::CCH(Me)F | H | Me | CF3 | O |
2.98 | H | C::CCH(Me)F | H | Me | CF2H | O |
2.99 | H | C::CCH(Me)F | F | Me | Me | O |
2.100 | H | C::CC(Me)2F | H | Me | CF3 | O |
2.101 | H | C::CC(Me)2F | H | Me | CF2H | O |
2.102 | H | C::CC(Me)2F | F | Me | Me | O |
2.103 | H | C::CCH2C(Me)3 | H | Me | CF3 | O |
2.104 | H | C::CCH2C(Me)3 | H | Me | CF2H | O |
2.105 | H | C::CCH2C(Me)3 | F | Me | Me | O |
2.106 | H | C::CCH(Me)2 | H | Me | CF2H | O |
2.107 | H | C::CCH(Me)2 | H | Me | CF2H | O |
2.108 | H | C::CCH(Me)2 | F | Me | Me | O |
2.109 | H | C::CCH2CH(Me)2 | H | Me | CF2H | O |
2.110 | H | C::CCH2CH(Me)2 | H | Me | CF2H | O |
2.111 | H | C::CCH2CH(Me)2 | F | Me | Me | O |
2.112 | H | CH2C::CCMe3 | H | Me | CF3 | O |
2.113 | H | CH2C::CCMe3 | H | Me | CF2H | O |
2.114 | H | CH2C::CCMe3 | F | Me | Me | O |
2.115 | H | CF2C::CCMe3 | H | Me | CF3 | O |
2.116 | H | CF2C::CCMe3 | H | Me | CF2H | O |
2.117 | H | CF2C::CCMe3 | F | Me | Me | O |
2.118 | H | CF2C::CMe | H | Me | CF3 | O |
2.119 | H | CF2C::CMe | H | Me | CF2H | O |
2.120 | H | CF2C::CCMe | F | Me | Me | O |
2.121 | H | CF2C::CH | H | Me | CF3 | O |
2.122 | H | CF2C::CH | H | Me | CF2H | O |
2.123 | H | CF2C::CH | F | Me | Me | O |
2.124 | H | CMe2C::CH | H | Me | CF3 | O |
2,125 | H | CMe2C::CH | H | Me | CF2H | O |
2.126 | H | CMe2C::CH | F | Me | Me | O |
2.127 | H | CHFC::CH | H | Me | CF3 | O |
2.128 | H | CHFC::CH | H | Me | CF2H | O |
2.129 | H | CHFC::CH | F | Me | Me | O |
2.130 | H | CHMeC::CH | H | Me | CF3 | O |
2.131 | H | CHMeC::CH | H | Me | CF2H | O |
2.132 | H | CHMeC::CH | F | Me | Me | O |
2.133 | H | CH(CF3)C::CH | H | Me | CF3 | O |
2.134 | H | CH(CF3)C::CH | H | Me | CF2H | O |
2.135 | H | CH(CF3)C::CH | F | Me | Me | O |
2.136 | H | C::C(1-F-环戊基) | H | Me | CF3 | O |
2.137 | H | C::C(1-F-环戊基) | H | Me | CHF2 | O |
2.138 | H | C::CCH2OMe | H | Me | CF3 | O |
2.139 | H | C::CCH2OMe | H | Me | CF2H | O |
2.140 | H | C::CCH2OMe | F | Me | Me | O |
2.141 | H | C::CCMe2OMe | H | Me | CF3 | O |
2.142 | H | C::CCMe2OMe | H | Me | CF2H | O |
2.143 | H | C::CCMe2OMe | F | Me | Me | O |
2.144 | H | C::CCMe2OCOMe | H | Me | CF3 | O |
2.145 | H | C::CCMe2OCOMe | H | Me | CF2H | O |
2.146 | H | C::CCF2Me | H | Me | CF3 | O |
2.147 | H | C::CCF2Me | H | Me | CF2H | O |
2.148 | H | C::CCF2Me | F | Me | Me | O |
2.149 | H | C::CC(Me)=CH2 | H | Me | CF3 | O |
2.150 | H | C::CC(Me)=CH2 | H | Me | CF2H | O |
2.151 | H | CH=CFCl | H | Me | CF3 | O |
2.152 | H | CH=CFCl | H | Me | CF2H | O |
2.153 | H | CH=CFCl | F | Me | Me | O |
2.154 | H | CH=CFBr | H | Me | CF3 | O |
2.155 | H | CH=CFBr | H | Me | CF2H | O |
2.156 | H | CH=CFBr | F | Me | Me | O |
2.157 | H | CH=CHBr | H | Me | CF3 | O |
2.158 | H | CH=CHBr | H | Me | CF2H | O |
2.159 | H | CH=CHBr | F | Me | Me | O |
2.160 | H | CH=CHF | H | Me | CF3 | O |
2.161 | H | CH=CHF | H | Me | CF2H | O |
2.162 | H | CH=CHF | F | Me | Me | O |
2.163 | H | CMe=CHCF3 | H | Me | CF3 | O |
2.164 | H | CMe=CHCF3 | H | Me | CF2H | O |
2.165 | H | CMe=CHCF3 | F | Me | Me | O |
2.166 | H | CH=CFCF3 | H | Me | CF3 | O |
2.167 | H | CH=CFCF3 | H | Me | CF2H | O |
2.168 | H | CH=CFCF3 | F | Me | Me | O |
2.169 | H | CH=CBrCF3 | H | Me | CF3 | O |
2.170 | H | CH=CBrCF3 | H | Me | CF2H | O |
2.171 | H | CH=CBrCF3 | F | Me | Me | O |
2.172 | H | CH=CHC2F5 | H | Me | CF3 | O |
2.173 | H | CH=CHC2F5 | H | Me | CF2H | O |
2.174 | H | CH=CHC2F5 | F | Me | Me | O |
2.175 | H | CH=CHCl | H | Me | CF3 | O |
2.176 | H | CH=CHCl | H | Me | CF2H | O |
2.177 | H | CH=CHCl | F | Me | Me | O |
2.178 | H | CH=C(CF3)2 | H | Me | CF3 | O |
2.179 | H | CH=C(CF3)2 | H | Me | CF2H | O |
2.180 | H | CH=C(CF3)2 | F | Me | Me | O |
2.181 | H | CMe=CFCl | H | Me | CF3 | O |
2.182 | H | CMe=CFCl | H | Me | CF2H | O |
2.183 | H | CMe=CFCl | F | Me | Me | O |
2.184 | H | CMe=CFBr | H | Me | CF3 | O |
2.185 | H | CMe=CFBr | H | Me | CF2H | O |
2.186 | H | CMe=CFBr | F | Me | Me | O |
2.187 | H | CMe=CF2 | H | Me | CF3 | O |
2.188 | H | CMe=CF2 | H | Me | CF2H | O |
2.189 | H | CMe=CF2 | F | Me | Me | O |
2.190 | H | CMe=CCl2 | H | Me | CF3 | O |
2.191 | H | CMe=CCl2 | H | Me | CF2H | O |
2.192 | H | CMe=CCl2 | F | Me | Me | O |
2.193 | H | CMe=CBr2 | H | Me | CF3 | O |
2.194 | H | CMe=CBr2 | H | Me | CF2H | O |
2.195 | H | CMe=CBr2 | F | Me | Me | O |
2.196 | H | CMe=CFCF3 | H | Me | CF3 | O |
2.197 | H | CMe=CFCF3 | H | Me | CF2H | O |
2.198 | H | CMe=CFCF3 | F | Me | Me | O |
2.199 | H | CMe=CClCF3 | H | Me | CF3 | O |
2.200 | H | CMe=CClCF3 | H | Me | CF2H | O |
2.201 | H | CMe=CClCF3 | F | Me | Me | O |
2.202 | H | CCF3=CF2 | H | Me | CF3 | O |
2.203 | H | CCF3=CF2 | H | Me | CF2H | O |
2.204 | H | CCF3=CF2 | F | Me | Me | O |
2.205 | H | CCF3=CCl2 | H | Me | CF3 | O |
2.206 | H | CCF3=CCl2 | H | Me | CF2H | O |
2.207 | H | CCF3=CCl2 | F | Me | Me | O |
2.208 | H | CCF3=CBr2 | H | Me | CF3 | O |
2.209 | H | CCF3=CBr2 | H | Me | CF2H | O |
2.210 | H | CCF3=CBr2 | F | Me | Me | O |
2.211 | H | CCF3=CH2 | H | Me | CF3 | O |
2.212 | H | CCF3=CH2 | H | Me | CF2H | O |
2.213 | H | CCF3=CH2 | F | Me | Me | O |
2.214 | H | CCF3=CFBr | H | Me | CF3 | O |
2.215 | H | CCF3=CFBr | H | Me | CF2H | O |
2.216 | H | CCF3=CFBr | F | Me | Me | O |
2.217 | H | CCF3=CHF | H | Me | CF3 | O |
2.218 | H | CCF3=CHF | H | Me | CF2H | O |
2.219 | H | CCF3=CHF | F | Me | Me | O |
2.220 | H | CCF3=CFCl | H | Me | CF3 | O |
2.221 | H | CCF3=CFCl | H | Me | CF2H | O |
2.222 | H | CCF3=CFCl | F | Me | Me | O |
2.223 | H | CCF3=CHCl | H | Me | CF3 | O |
2.224 | H | CCF3=CHCl | H | Me | CF2H | O |
2.225 | H | CCF3=CHCl | F | Me | Me | O |
2.226 | H | CH=CFCF2Cl | H | Me | CF3 | O |
2.227 | H | CH=CFCF2Cl | H | Me | CF2H | O |
2.228 | H | CH=CFCF2Cl | F | Me | Me | O |
2.229 | H | CH=CClCF2Cl | H | Me | CF3 | O |
2.230 | H | CH=CClCF2Cl | H | Me | CF2H | O |
2.231 | H | CH=CClCF2Cl | F | Me | Me | O |
2.232 | H | CH2CF=CF2 | H | Me | CF3 | O |
2.233 | H | CH2CF=CF2 | H | Me | CF2H | O |
2.234 | H | CH2CF=CF2 | F | Me | Me | O |
2.235 | H | CF=CFBr | H | Me | CF3 | O |
2.236 | H | CF=CFBr | H | Me | CF2H | O |
2.237 | H | CF=CFBr | F | Me | Me | O |
2.238 | H | CH2CH=CF2 | H | Me | CF3 | O |
2.239 | H | CH2CH=CF2 | H | Me | CF2H | O |
2.240 | H | CH2CH=CF2 | F | Me | Me | O |
2.241 | H | CH2CH=CCl2 | H | Me | CF3 | O |
2.242 | H | CH2CH=CCl2 | H | Me | CF2H | O |
2.243 | H | CH2CH=CCl2 | F | Me | Me | O |
2.244 | H | CH2CH=CBr2 | H | Me | CF3 | O |
2.245 | H | CH2CH=CBr2 | H | Me | CF2H | O |
2.246 | H | CH2CH=CBr2 | F | Me | Me | O |
2.247 | H | CCl=CF2 | H | Me | CF3 | O |
2.248 | H | CCl=CF2 | H | Me | CF2H | O |
2.249 | H | CCl=CF2 | F | Me | Me | O |
表2提供了249种式(Ib)化合物,其中R1、R7、R8、R9、R10和X是如表2中所定义的。
表3
化合物编号 | R1 | R7 | R9 | R10 | X |
3.01 | H | C::CH | Me | CF3 | O |
3.02 | H | C::CH | Me | CF3 | S |
3.03 | H | C::CH | Me | CF2H | O |
3.04 | 炔丙基 | C::CH | Me | CF3 | O |
3.05 | H | C::CH | Me | Me | O |
3.06 | H | C::CH | CH2OMe | CF3 | O |
3.07 | 丙二烯基 | C::CH | Me | CF3 | O |
3.08 | H | C::CSiMe3 | Me | CF3 | O |
3.09 | H | C::CSiMe3 | Me | CF3 | S |
3.10 | H | C::CSiMe3 | Me | CF2H | O |
3.11 | H | C::CSiMe3 | Me | Me | O |
3.12 | H | C::CCl | Me | CF3 | O |
3.13 | H | C::CCl | Me | CF2H | O |
3.14 | H | C::CCl | Me | Me | O |
3.15 | H | C::CBr | Me | CF3 | O |
3.16 | H | C::CBr | Me | CF2H | O |
3.17 | H | C::CBr | Me | Me | O |
3.18 | H | C::CCF3 | Me | CF3 | O |
3.19 | H | C::CCF3 | Me | CF2H | O |
3.20 | H | C::CCF3 | Me | Me | O |
3.21 | 丙二烯基 | C::CCF3 | Me | CF3 | O |
3.22 | H | CH=CH2 | Me | CF3 | O |
3.23 | H | CH=CH2 | Me | CF3 | S |
3.24 | H | CH=CH2 | Me | CF2H | O |
3.25 | 炔丙基 | CH=CH2 | Me | CF3 | O |
3.26 | H | CH=CH2 | Me | Me | O |
3.27 | H | CH=CH2 | CH2OMe | CF3 | O |
3.28 | 丙二烯基 | CH=CH2 | Me | CF3 | O |
3.29 | H | CH=CF2 | Me | CF3 | O |
3.30 | H | CH=CF2 | Me | CF2H | O |
3.31 | H | CH=CF2 | Me | Me | O |
3.32 | H | CH=CCl2 | Me | CF3 | O |
3.33 | H | CH=CCl2 | Me | CF2H | O |
3.34 | H | CH=CCl2 | Me | Me | O |
3.35 | H | CH=CBr2 | Me | CF3 | O |
3.36 | H | CH=CBr2 | Me | CF2H | O |
3.37 | H | CH=CBr2 | Me | Me | O |
3.38 | H | CF=CF2 | Me | CF3 | O |
3.39 | H | CF=CF2 | Me | CF2H | O |
3.40 | H | CF=CF2 | Me | Me | O |
3.41 | H | CCl=CH2 | Me | CF3 | O |
3.42 | H | CCl=CH2 | Me | CF2H | O |
3.43 | H | CCl=CH2 | Me | Me | O |
3.44 | H | CBr=CH2 | Me | CF3 | O |
3.45 | H | CBr=CH2 | Me | CF2H | O |
3.46 | H | CBr=CH2 | Me | Me | O |
3.47 | H | CF=CHF | Me | CF3 | O |
3.48 | H | CF=CHF | Me | CF2H | O |
3.49 | H | CF=CHF | Me | Me | O |
3.50 | H | CH=CHSiMe3 | Me | CF3 | O |
3.51 | H | CH=CHSiMe3 | Me | CF2H | O |
3.52 | H | CH=CHSiMe3 | Me | Me | O |
3.53 | H | CH=CHCF3 | Me | CF3 | O |
3.54 | H | CH=CHCF3 | Me | CF2H | O |
3.55 | H | CH=CHCF3 | Me | Me | O |
3.56 | H | CH=CClCF3 | Me | CF3 | O |
3.57 | H | CH=CClCF3 | Me | CF2H | O |
3.58 | H | CH=CClCF3 | Me | Me | O |
3.59 | H | CH2C::CH | Me | CF3 | O |
3.60 | H | CH2C::CH | Me | CF2H | O |
3.61 | H | CH2C::CH | Me | Me | O |
3.62 | H | CH2C::CH | CH2OMe | CF3 | O |
3.63 | H | CH2C::CSiMe3 | Me | CF3 | O |
3.64 | H | CH2C::CSiMe3 | Me | CF2H | O |
3.65 | H | CH2C::CSiMe3 | Me | Me | O |
3.66 | H | C::CCMe3 | Me | CF3 | O |
3.67 | H | C::CCMe3 | Me | CF2H | O |
3.68 | H | C::CCMe3 | Me | Me | O |
3.69 | H | C::CMe | Me | CF3 | O |
3.70 | H | C::CMe | Me | CF2H | O |
3.71 | H | C::CMe | Me | Me | O |
3.72 | COMe | C::CH | Me | CF3 | O |
3.73 | H | C::CH | CF2H | CF2H | O |
3.74 | H | C::CH | CF2H | CF3 | O |
3.75 | H | C::CH | Me | CH2F | O |
3.76 | H | C::CSiMe3 | Me | CH2F | O |
3.77 | H | C::C(环丙基) | Me | CF3 | O |
3.78 | H | C::C(环丙基) | Me | CHF2 | O |
3.79 | H | SiMe3 | Me | CH2F | O |
3.80 | H | SiMe3 | Me | CF3 | O |
3.81 | H | SiMe3 | Me | CHF2 | O |
3.82 | H | C::CF | Me | CF3 | O |
3.83 | H | C::CF | Me | CF2H | O |
3.84 | H | C::CF | Me | Me | O |
3.85 | H | C::CCF2Cl | Me | CF3 | O |
3.86 | H | C::CCF2Cl | Me | CF2H | O |
3.87 | H | C::CCF2Cl | Me | Me | O |
3.88 | H | C::CCF2H | Me | CF3 | O |
3.89 | H | C::CCF2H | Me | CF2H | O |
3.90 | H | C::CCF2H | Me | Me | O |
3.91 | H | C::CCF2Br | Me | CF3 | O |
3.92 | H | C::CCF2Br | Me | CF2H | O |
3.93 | H | C::CCF2Br | Me | Me | O |
3.94 | H | C::CCH2F | Me | CF3 | O |
3.95 | H | C::CCH2F | Me | CF2H | O |
3.96 | H | C::CCH2F | Me | Me | O |
3.97 | H | C::CCH(Me)F | Me | CF3 | O |
3.98 | H | C::CCH(Me)F | Me | CF2H | O |
3.99 | H | C::CCH(Me)F | Me | Me | O |
3.100 | H | C::CC(Me)2F | Me | CF3 | O |
3.101 | H | C::CC(Me)2F | Me | CF2H | O |
3.102 | H | C::CC(Me)2F | Me | Me | O |
3.103 | H | C::CCH2C(Me)3 | Me | CF3 | O |
3.104 | H | C::CCH2C(Me)3 | Me | CF2H | O |
3.105 | H | C::CCH2C(Me)3 | Me | Me | O |
3.106 | H | C::CCH(Me)2 | Me | CF3 | O |
3.107 | H | C::CCH(Me)2 | Me | CF2H | O |
3.108 | H | C::CCH(Me)2 | Me | Me | O |
3.109 | H | C::CCH2CH(Me)2 | Me | CF3 | O |
3.110 | H | C::CCH2CH(Me)2 | Me | CF2H | O |
3.111 | H | C::CCH2CH(Me)2 | Me | Me | O |
3.112 | H | CH2C::CCMe3 | Me | CF3 | O |
3.113 | H | CH2C::CCMe3 | Me | CF2H | O |
3.114 | H | CH2C::CCMe3 | Me | Me | O |
3.115 | H | CF2C::CCMe3 | Me | CF3 | O |
3.116 | H | CF2C::CCMe3 | Me | CF2H | O |
3.117 | H | CF2C::CCMe3 | Me | Me | O |
3.118 | H | CF2C::CMe | Me | CF3 | O |
3.119 | H | CF2C::CMe | Me | CF2H | O |
3.120 | H | CF2C::CCMe | Me | Me | O |
3.121 | H | CF2C::CH | Me | CF3 | O |
3.122 | H | CF2C::CH | Me | CF2H | O |
3.123 | H | CF2C::CH | Me | Me | O |
3.124 | H | CMe2C::CH | Me | CF3 | O |
2,125 | H | CMe2C::CH | Me | CF2H | O |
3.126 | H | CMe2C::CH | Me | Me | O |
3.127 | H | CHFC::CH | Me | CF3 | O |
3.128 | H | CHFC::CH | Me | CF2H | O |
3.129 | H | CHFC::CH | Me | Me | O |
3.130 | H | CHMeC::CH | Me | CF3 | O |
3.131 | H | CHMeC::CH | Me | CF2H | O |
3.132 | H | CHMeC::CH | Me | Me | O |
3.133 | H | CH(CF3)C::CH | Me | CF3 | O |
3.134 | H | CH(CF3)C::CH | Me | CF2H | O |
3.135 | H | CH(CF3)C::CH | Me | Me | O |
3.136 | H | C::C(1-F-环戊基) | Me | CF3 | O |
3.137 | H | C::C(1-F-环戊基) | Me | CHF2 | O |
3.138 | H | C::CCH2OMe | Me | CF3 | O |
3.139 | H | C::CCH2OMe | Me | CF2H | O |
3.140 | H | C::CCH2OMe | Me | Me | O |
3.141 | H | C::CCMe2OMe | Me | CF3 | O |
3.142 | H | C::CCMe2OMe | Me | CF2H | O |
3.143 | H | C::CCMe2OMe | Me | Me | O |
3.144 | H | C::CCMe2OCOMe | Me | CF3 | O |
3.145 | H | C::CCMe2OCOMe | Me | CF2H | O |
3.146 | H | C::CCF2Me | Me | CF3 | O |
3.147 | H | C::CCF2Me | Me | CF2H | O |
3.148 | H | C::CCF2Me | Me | Me | O |
3.149 | H | C::CC(Me)=CH2 | Me | CF3 | O |
3.150 | H | C::CC(Me)=CH2 | Me | CF2H | O |
3.151 | H | CH=CFCl | Me | CF3 | O |
3.152 | H | CH=CFCl | Me | CF2H | O |
3.153 | H | CH=CFCl | Me | Me | O |
3.154 | H | CH=CFBr | Me | CF3 | O |
3.155 | H | CH=CFBr | Me | CF2H | O |
3.156 | H | CH=CFBr | Me | Me | O |
3.157 | H | CH=CHBr | Me | CF3 | O |
3.158 | H | CH=CHBr | Me | CF2H | O |
3.159 | H | CH=CHBr | Me | Me | O |
3.160 | H | CH=CHF | Me | CF3 | O |
3.161 | H | CH=CHF | Me | CF2H | O |
3.162 | H | CH=CHF | Me | Me | O |
3.163 | H | CMe=CHCF3 | Me | CF3 | O |
3.164 | H | CMe=CHCF3 | Me | CF2H | O |
3.165 | H | CMe=CHCF3 | Me | Me | O |
3.166 | H | CH=CFCF3 | Me | CF3 | O |
3.167 | H | CH=CFCF3 | Me | CF2H | O |
3.168 | H | CH=CFCF3 | Me | Me | O |
3.169 | H | CH=CBrCF3 | Me | CF3 | O |
3.170 | H | CH=CBrCF3 | Me | CF2H | O |
3.171 | H | CH=CBrCF3 | Me | Me | O |
3.172 | H | CH=CHC2F5 | Me | CF3 | O |
3.173 | H | CH=CHC2F5 | Me | CF2H | O |
3.174 | H | CH=CHC2F5 | Me | Me | O |
3.175 | H | CH=CHCl | Me | CF3 | O |
3.176 | H | CH=CHCl | Me | CF2H | O |
3.177 | H | CH=CHCl | Me | Me | O |
3.178 | H | CH=C(CF3)2 | Me | CF3 | O |
3.179 | H | CH=C(CF3)2 | Me | CF2H | O |
3.180 | H | CH=C(CF3)2 | Me | Me | O |
3.181 | H | CMe=CFCl | Me | CF3 | O |
3.182 | H | CMe=CFCl | Me | CF2H | O |
3.183 | H | CMe=CFCl | Me | Me | O |
3.184 | H | CMe=CFBr | Me | CF3 | O |
3.185 | H | CMe=CFBr | Me | CF2H | O |
3.186 | H | CMe=CFBr | Me | Me | O |
3.187 | H | CMe=CF2 | Me | CF3 | O |
3.188 | H | CMe=CF2 | Me | CF2H | O |
3.189 | H | CMe=CF2 | Me | Me | O |
3.190 | H | CMe=CCl2 | Me | CF3 | O |
3.191 | H | CMe=CCl2 | Me | CF2H | O |
3.192 | H | CMe=CCl2 | Me | Me | O |
3.193 | H | CMe=CBr2 | Me | CF3 | O |
3.194 | H | CMe=CBr2 | Me | CF2H | O |
3.195 | H | CMe=CBr2 | Me | Me | O |
3.196 | H | CMe=CFCF3 | Me | CF3 | O |
3.197 | H | CMe=CFCF3 | Me | CF2H | O |
3.198 | H | CMe=CFCF3 | Me | Me | O |
3.199 | H | CMe=CClCF3 | Me | CF3 | O |
3.200 | H | CMe=CClCF3 | Me | CF2H | O |
3.201 | H | CMe=CClCF3 | Me | Me | O |
3.202 | H | CCF3=CF2 | Me | CF3 | O |
3.203 | H | CCF3=CF2 | Me | CF2H | O |
3.204 | H | CCF3=CF2 | Me | Me | O |
3.205 | H | CCF3=CCl2 | Me | CF3 | O |
3.206 | H | CCF3=CCl2 | Me | CF2H | O |
3.207 | H | CCF3=CCl2 | Me | Me | O |
3.208 | H | CCF3=CBr2 | Me | CF3 | O |
3.209 | H | CCF3=CBr2 | Me | CF2H | O |
3.210 | H | CCF3=CBr2 | Me | Me | O |
3.211 | H | CCF3=CH2 | Me | CF3 | O |
3.212 | H | CCF3=CH2 | Me | CF2H | O |
3.213 | H | CCF3=CH2 | Me | Me | O |
3.214 | H | CCF3=CFBr | Me | CF3 | O |
3.215 | H | CCF3=CFBr | Me | CF2H | O |
3.216 | H | CCF3=CFBr | Me | Me | O |
3.217 | H | CCF3=CHF | Me | CF3 | O |
3.218 | H | CCF3=CHF | Me | CF2H | O |
3.219 | H | CCF3=CHF | Me | Me | O |
3.220 | H | CCF3=CFCl | Me | CF3 | O |
3.221 | H | CCF3=CFCl | Me | CF2H | O |
3.222 | H | CCF3=CFCl | Me | Me | O |
3.223 | H | CCF3=CHCl | Me | CF3 | O |
3.224 | H | CCF3=CHCl | Me | CF2H | O |
3.225 | H | CCF3=CHCl | Me | Me | O |
3.226 | H | CH=CFCF2Cl | Me | CF3 | O |
3.227 | H | CH=CFCF2Cl | Me | CF2H | O |
3.228 | H | CH=CFCF2Cl | Me | Me | O |
3.229 | H | CH=CClCF2Cl | Me | CF3 | O |
3.230 | H | CH=CClCF2Cl | Me | CF2H | O |
3.231 | H | CH=CClCF2Cl | Me | Me | O |
3.232 | H | CH2CF=CF2 | Me | CF3 | O |
3.233 | H | CH2CF=CF2 | Me | CF2H | O |
3.234 | H | CH2CF=CF2 | Me | Me | O |
3.235 | H | CF=CFBr | Me | CF3 | O |
3.236 | H | CF=CFBr | Me | CF2H | O |
3.237 | H | CF=CFBr | Me | Me | O |
3.238 | H | CH2CH=CF2 | Me | CF3 | O |
3.239 | H | CH2CH=CF2 | Me | CF2H | O |
3.240 | H | CH2CH=CF2 | Me | Me | O |
3.241 | H | CH2CH=CCl2 | Me | CF3 | O |
3.242 | H | CH2CH=CCl2 | Me | CF2H | O |
3.243 | H | CH2CH=CCl2 | Me | Me | O |
3.244 | H | CH2CH=CBr2 | Me | CF3 | O |
3.245 | H | CH2CH=CBr2 | Me | CF2H | O |
3.246 | H | CH2CH=CBr2 | Me | Me | O |
3.247 | H | CCl=CF2 | Me | CF3 | O |
3.248 | H | CCl=CF2 | Me | CF2H | O |
3.249 | H | CCl=CF2 | Me | Me | O |
3.250 | H | C::CCMe2OH | Me | CF3 | O |
3.251 | H | C::CCH2CH3 | Me | CF2H | O |
3.252 | H | C::CCH2CH3 | Me | Me | O |
3.253 | H | C::CCH2CH3 | Me | CF3 | O |
3.254 | H | C::CCF=CF2 | Me | CF3 | O |
3.255 | H | C::CCF=CF2 | Me | CF2H | O |
3.256 | H | C::CCHFCl | Me | CF3 | O |
3.257 | H | C::CCHFCl | Me | CF2H | O |
3.258 | H | C::CCHFCl | Me | Me | O |
3.259 | H | CH=CFC2F5 | Me | CF3 | O |
3.260 | H | CH=CFC2F5 | Me | CF2H | O |
3.261 | H | CH=CFC2F5 | Me | Me | O |
3.262 | H | C::CCF2CH2CH3 | Me | CF3 | O |
3.263 | H | C::CCF2CH2CH3 | Me | CF2H | O |
3.264 | H | C::CCF2CH2CH3 | Me | Me | O |
3.265 | H | C::CCHFCH2CH3 | Me | CF3 | O |
3.266 | H | C::CCHFCH2CH3 | Me | CF2H | O |
3.267 | H | C::CCHFCH2CH3 | Me | Me | O |
3.268 | H | C::CCF(CF3)2 | Me | CF3 | O |
3.269 | H | C::CCF(CF3)2 | Me | CF2H | O |
3.270 | H | C::CCF(CF3)2 | Me | Me | O |
3.271 | H | CH=CClC2F5 | Me | CF3 | O |
3.272 | H | CH=CClC2F5 | Me | CF2H | O |
3.273 | H | CH=CClC2F5 | Me | Me | O |
3.274 | H | C::CC2F5 | Me | CF3 | O |
3.275 | H | C::CC2F5 | Me | CF2H | O |
3.276 | H | C::CC2F5 | Me | Me | O |
表3提供了276种式(Ic)化合物:
其中R1、R7、R9、R10和X是如表3中所定义的。
表3提供了276种式(IcA)化合物,其中R1、R7、R9、R10和X是如表3中所定义的。
表3提供了276种式(IcB)化合物,其中R1、R7、R9、R10和X是如表3中所定义的。
表3提供了276种式(IcC)化合物,其中R1、R7、R9、R10和X是如表3中所定义的。
表3提供了276种式(IcD)化合物,其中R1、R7、R9、R10和X是如表3中所定义的。
表3提供了276种式(IcE)化合物,其中R1、R7、R9、R10和X是如表3中所定义的。
表3提供了276种式(IcF)化合物,其中R1、R7、R9、R10和X是如表3中所定义的。
表3提供了276种式(IcG)化合物,其中R1、R7、R9、R10和X是如表3中所定义的。
表4提供了3种式(Id)化合物:
其中R1、R7、R9和R10是如表4中所定义的。
表4
化合物编号 | R1 | R7 | R9 | R10 |
4.01 | H | C::CH | Me | CF3 |
4.02 | H | C::CSiMe3 | Me | CF3 |
4.03 | H | CH=CH2 | Me | CF3 |
表5提供了15种式(Ie)化合物:
其中R1、R7、R8、R9和R10是如表5中所定义的。
表5
化合物编号 | R1 | R7 | R8 | R9 | R10 |
5.01 | H | C::CH | H | H | CF3 |
5.02 | H | C::CH | Me | Me | Me |
5.03 | H | C::CH | H | Me | CF3 |
5.04 | H | C::CH | Me | Me | H |
5.05 | COMe | C::CH | Me | Me | H |
5.06 | COMe | C::CH | Me | Me | Me |
5.07 | COEt | C::CH | Me | Me | Me |
5.08 | H | C::CSiMe3 | H | H | CF3 |
5.09 | H | C::CSiMe3 | Me | Me | Me |
5.10 | H | C::CSiMe3 | H | Me | CF3 |
5.11 | H | C::CSiMe3 | Me | Me | H |
5.12 | H | C::CSiMe3 | H | H | CF3 |
5.13 | H | CH=CH2 | Me | Me | Me |
5.14 | H | CH=CH2 | H | Me | CF3 |
5.15 | H | CH=CH2 | Me | Me | H |
表6提供了15种式(If)化合物:
其中R1、R7、R8、R9和R10是如表6中所定义的。
表6
化合物编号 | R1 | R7 | R8 | R9 | R10 |
6.01 | H | C::CH | H | H | CF3 |
6.02 | H | C::CH | Me | Me | Me |
6.03 | H | C::CH | H | Me | CF3 |
6.04 | H | C::CH | Me | Me | H |
6.05 | COMe | C::CH | Me | Me | H |
6.06 | COMe | C::CH | Me | Me | Me |
6.07 | COEt | C::CH | Me | Me | Me |
6.08 | H | C::CSiMe3 | H | H | CF3 |
6.09 | H | C::CSiMe3 | Me | Me | Me |
6.10 | H | C::CSiMe3 | H | Me | CF3 |
6.11 | H | C::CSiMe3 | Me | Me | H |
6.12 | H | C::CSiMe3 | H | H | CF3 |
6.13 | H | CH=CH2 | Me | Me | Me |
6.14 | H | CH=CH2 | H | Me | CF3 |
6.15 | H | CH=CH2 | Me | Me | H |
表7提供了10种式(Ig)化合物:
其中R1、R7、R8和X是如表7中所定义的。
表7
化合物编号 | R1 | R7 | R8 | X |
7.01 | H | C::CH | CF3 | O |
7.02 | H | C::CH | Me | O |
7.03 | H | C::CH | CF3 | S |
7.04 | COMe | C::CH | Me | O |
7.05 | H | C::CSiMe3 | CF3 | O |
7.06 | H | C::CSiMe3 | Me | O |
7.07 | H | CH=CH2 | CF3 | O |
7.08 | H | CH=CH2 | CF3 | O |
7.09 | 炔丙基 | CH=CH2 | Me | O |
7.10 | 丙二烯基 | CH=CH2 | Me | O |
表8提供了10种式(Ih)化合物:
其中R1、R7、R8和X是如表8中所定义的。
表8
化合物编号 | R1 | R7 | R8 | X |
8.01 | H | C::CH | CF3 | O |
8.02 | H | C::CH | Me | O |
8.03 | H | C::CH | CF3 | S |
8.04 | COMe | C::CH | Me | O |
8.05 | H | C::CSiMe3 | CF3 | O |
8.06 | H | C::CSiMe3 | Me | O |
8.07 | H | CH=CH2 | CF3 | O |
8.08 | H | CH=CH2 | CF3 | O |
8.09 | 炔丙基 | CH=CH2 | Me | O |
8.10 | 丙二烯基 | CH=CH2 | Me | O |
表9
化合物编号 | R1 | R7 | R8 |
9.01 | H | C::CH | Cl |
9.02 | H | C::CH | CF3 |
9.03 | COMe | C::CH | Cl |
9.04 | H | C::CH | Br |
9.05 | COCH2OMe | C::CH | Cl |
9.06 | H | C::CSiMe3 | Cl |
9.07 | H | C::CSiMe3 | CF3 |
9.08 | H | C::CSiMe3 | Br |
9.09 | H | CH=CH2 | CF3 |
9.10 | H | CH=CH2 | Br |
9.11 | H | CH=CH2 | Cl |
9.12 | H | CH=CH2 | CH3 |
9.13 | 炔丙基 | CH=CH2 | Cl |
9.14 | 丙二烯基 | CH=CH2 | Cl |
9.15 | H | C::CCl | Cl |
9.16 | H | C::CCl | CF3 |
9.17 | H | C::CCl | Br |
9.18 | H | C::CBr | Cl |
9.19 | H | C::CBr | CF3 |
9.20 | H | C::CBr | Br |
9.21 | H | C::CCF3 | Cl |
9.22 | H | C::CCF3 | CF3 |
9.23 | H | C::CCF3 | Br |
9.24 | H | CH=CF2 | CF3 |
9.25 | H | CH=CF2 | Br |
9.26 | H | CH=CF2 | Cl |
9.27 | H | CCl=CH2 | CF3 |
9.28 | H | CCl=CH2 | Br |
9.29 | H | CCl=CH2 | Cl |
9.30 | H | CBr=CH2 | CF3 |
9.31 | H | CBr=CH2 | Br |
9.32 | H | CBr=CH2 | Cl |
9.33 | H | CF=CHF | CF3 |
9.34 | H | CF=CHF | Br |
9.35 | H | CF=CHF | Cl |
9.36 | H | CH=CHCF3 | CF3 |
9.37 | H | CH=CHCF3 | Br |
9.38 | H | CH=CHCF3 | Cl |
9.39 | H | CH=CClCF3 | CF3 |
9.40 | H | CH=CClCF3 | Br |
9.41 | H | CH=CClCF3 | Cl |
9.42 | H | CH2C::CH | CF3 |
9.43 | H | CH2C::CH | Br |
9.44 | H | CH2C::CH | Cl |
9.45 | H | CH2C::CSiMe3 | CF3 |
9.46 | H | CH2C::CSiMe3 | Br |
9.47 | H | CH2C::CSiMe3 | Cl |
9.48 | H | C::CMe | CF3 |
9.49 | H | C::CMe | Br |
9.50 | H | C::CMe | Cl |
9.51 | H | CH=CCl2 | CF3 |
9.52 | H | CH=CCl2 | Br |
9.53 | H | CH=CCl2 | Cl |
9.54 | H | CH=CHSiMe3 | CF3 |
9.55 | H | CH=CHSiMe3 | Br |
9.56 | H | CH=CHSiMe3 | Cl |
9.57 | H | C::C(环丙基) | Cl |
9.58 | H | SiMe3 | Cl |
9.59 | H | C::CCMe3 | Cl |
9.60 | H | CH=CBr2 | CF3 |
9.61 | H | CH=CBr2 | Br |
9.62 | H | CH=CBr2 | Cl |
9.63 | H | CF=CF2 | CF3 |
9.64 | H | CF=CF2 | Br |
9.65 | H | CF=CF2 | Cl |
9.66 | H | C::CCMe3 | CF3 |
9.67 | H | C::CCMe3 | Br |
9.68 | 丙二烯基 | C::CCMe3 | Cl |
9.69 | H | C::C(环丙基) | CF3 |
9.70 | H | C::C(环丙基) | Br |
9.71 | H | C::CF | CF3 |
9.72 | H | C::CF | Br |
9.73 | H | C::CF | Cl |
9.74 | H | C::CCF2Cl | Cl |
9.75 | H | C::CCF2Cl | CF3 |
9.76 | H | C::CCF2Cl | Br |
9.77 | H | C::CCF2H | Cl |
9.78 | H | C::CCF2H | CF3 |
9.79 | H | C::CCF2H | Br |
9.80 | H | C::CCF2Br | Cl |
9.81 | H | C::CCF2Br | CF3 |
9.82 | H | C::CCF2Br | Br |
9.83 | H | C::CCH2F | Cl |
9.84 | H | C::CCH2F | CF3 |
9.85 | H | C::CCH2F | Br |
9.86 | H | C::CCH(Me)F | Cl |
9.87 | H | C::CCH(Me)F | CF3 |
9.88 | H | C::CCH(Me)F | Br |
9.89 | H | C::CC(Me)2F | Cl |
9.90 | H | C::CC(Me)2F | CF3 |
9.91 | H | C::CC(Me)2F | Br |
9.92 | H | C::CCH2CMe3 | Cl |
9.93 | H | C::CCH2CMe3 | Br |
9.94 | H | C::CCHMe2 | CF3 |
9.95 | H | C::CCHMe2 | Br |
9.96 | H | C::CCHMe2 | Cl |
9.97 | H | C::CCH2CHMe2 | CF3 |
9.98 | H | C::CCH2CHMe2 | Br |
9.99 | H | C::CCH2CHMe2 | Cl |
9.100 | H | CF2C::CMe | CF3 |
9.101 | H | CF2C::CMe | Br |
9.102 | H | CF2C::CMe | Cl |
9.103 | H | CF2C::CH | CF3 |
9.104 | H | CF2C::CH | Br |
9.105 | H | CF2C::CH | Cl |
9.106 | H | CHFC::CH | CF3 |
9.107 | H | CHFC::CH | Br |
9.108 | H | CHFC::CH | Cl |
9.109 | H | C::C(1-F-环戊基) | CF3 |
9.110 | H | C::C(1-F-环戊基) | Br |
9.111 | H | C::C(1-F-环戊基) | Cl |
9.112 | H | C::CCH2OMe | Cl |
9.113 | H | C::CCH2OMe | Br |
9.114 | H | C::CCH2OMe | CF3 |
9.115 | H | C::CCMe2OMe | Cl |
9.116 | H | C::CCMe2OMe | Br |
9.117 | H | C::CCMe2OMe | CF3 |
9.118 | H | C::CCMe2OCOMe | Cl |
9.119 | H | C::CCMe2OCOMe | Br |
9.120 | H | C::CCMe2OCOMe | CF3 |
9.121 | H | C::CCF2Me | Cl |
9.122 | H | C::CCF2Me | Br |
9.123 | H | C::CCF2Me | CF3 |
9.124 | H | CH=CFCl | CF3 |
9.125 | H | CH=CFCl | Br |
9.126 | H | CH=CFCl | Cl |
9.127 | H | CH=CFBr | CF3 |
9.128 | H | CH=CFBr | Br |
9.129 | H | CH=CFBr | Cl |
9.130 | H | CH=CHBr | CF3 |
9.131 | H | CH=CHBr | Br |
9.132 | H | CH=CHBr | Cl |
9.133 | H | CMe=CHCF3 | CF3 |
9.134 | H | CMe=CHCF3 | Br |
9.135 | H | CMe=CHCF3 | Cl |
9.136 | H | CH=CFCF3 | CF3 |
9.137 | H | CH=CFCF3 | Br |
9.138 | H | CH=CFCF3 | Cl |
9.139 | H | CH=CBrCF3 | CF3 |
9.140 | H | CH=CBrCF3 | Br |
9.141 | H | CH=CBrCF3 | Cl |
9.142 | H | CH=CHC2F5 | CF3 |
9.143 | H | CH=CHC2F5 | Br |
9.144 | H | CH=CHC2F5 | Cl |
9.145 | H | CH=CHCl | CF3 |
9.146 | H | CH=CHCl | Br |
9.147 | H | CH=CHCl | Cl |
9.148 | H | CH=C(CF3)2 | Cl |
9.149 | H | CMe=CFCl | CF3 |
9.150 | H | CMe=CFCl | Br |
9.151 | H | CMe=CFCl | Cl |
9.152 | H | CMe=CFBr | CF3 |
9.153 | H | CMe=CFBr | Br |
9.154 | H | CMe=CFBr | Cl |
9.155 | H | CMe=CF2 | CF3 |
9.156 | H | CMe=CF2 | Br |
9.157 | H | CMe=CF2 | Cl |
9.158 | H | CMe=CCl2 | CF3 |
9.159 | H | CMe=CCl2 | Br |
9.160 | H | CMe=CCl2 | Cl |
9.161 | H | CMe=CBr2 | CF3 |
9.162 | H | CMe=CBr2 | Br |
9.163 | H | CMe=CBr2 | Cl |
9.164 | H | CCF3=CF2 | CF3 |
9.165 | H | CCF3=CF2 | Br |
9.166 | H | CCF3=CF2 | Cl |
9.167 | H | CCF3=CCl2 | CF3 |
9.168 | H | CCF3=CCl2 | Br |
9.169 | H | CCF3=CCl2 | Cl |
9.170 | H | CCF3=CBr2 | CF3 |
9.171 | H | CCF3=CBr2 | Br |
9.172 | H | CCF3=CBr2 | Cl |
9.173 | H | CCF3=CH2 | CF3 |
9.174 | H | CCF3=CH2 | Br |
9.175 | H | CCF3=CH2 | Cl |
9.176 | H | CCF3=CFBr | CF3 |
9.177 | H | CCF3=CFBr | Br |
9.178 | H | CCF3=CFBr | Cl |
9.179 | H | CCF3=CFCl | CF3 |
9.180 | H | CCF3=CFCl | Br |
9.181 | H | CCF3=CFCl | Cl |
9.182 | H | CH=CFCF2Cl | CF3 |
9.183 | H | CH=CFCF2Cl | Br |
9.184 | H | CH=CFCF2Cl | Cl |
9.185 | H | CH=CClCF2Cl | Cl |
9.186 | H | CH2CF=CF2 | CF3 |
9.187 | H | CH2CF=CF2 | Br |
9.188 | H | CH2CF=CF2 | Cl |
9.189 | H | CF=CFBr | Cl |
9.190 | H | CH2CH=CF2 | Cl |
9.191 | H | CH2CH=CCl2 | Cl |
9.192 | H | CH2CH=CBr2 | Cl |
9.193 | H | CH2CH=CBr2 | CF3 |
9.194 | H | CH2CH=CBr2 | Br |
9.195 | H | CCl=CF2 | Cl |
9.196 | H | C::CMe | CHF2 |
9.197 | H | C::CCHMe2 | CHF2 |
9.198 | H | C::CCH2CHMe2 | CHF2 |
9.199 | H | C::CCF3 | CHF2 |
9.200 | H | C::CH | CHF2 |
9.201 | H | C::CCH2SiMe3 | Cl |
9.202 | H | C::CCH2CF3 | Cl |
9.203 | H | C::CSi(Me)2CMe3 | Cl |
9.204 | H | C::CCH2CH3 | Cl |
9.205 | H | C::CCF=CF2 | Cl |
9.206 | H | C::CCHFCl | Cl |
9.207 | H | CH=CFC2F5 | Cl |
9.208 | H | C::CCF2CH2CH3 | Cl |
9.209 | H | C::CCHFCH2CH3 | Cl |
9.210 | H | C::CCF(CF3)2 | Cl |
9.211 | H | CH=CClC2F5 | Cl |
9.212 | H | C::CC2F5 | Cl |
表9提供了212种式(Ii)化合物:
其中R1、R7和R8是如表9中所定义的。
表9提供了212种式(IiA)化合物,其中R1、R7和R8是如表9中所定义的。
表9提供了212种式(IiB)化合物,其中R1、R7和R8是如表9中所定义的。
表9提供了212种式(IiC)化合物,其中R1、R7和R8是如表9中所定义的。
表9还提供了212种式(IiD)化合物,其中R1、R7和R8是如表9中所定义的。
表10提供了14种式(Ij)化合物:
其中R1、R7和R8是如表10中所定义的。
表10
化合物编号 | R1 | R7 | R8 |
10.01 | H | C::CH | Cl |
10.02 | H | C::CH | CF3 |
10.03 | COMe | C::CH | Cl |
10.04 | H | C::CH | Br |
10.05 | COCH2OMe | C::CH | Cl |
10.06 | H | C::CSiMe3 | Cl |
10.07 | H | C::CSiMe3 | CF3 |
10.08 | H | C::CSiMe3 | Br |
10.09 | H | CH=CH2 | CF3 |
10.10 | H | CH=CH2 | Br |
10.11 | H | CH=CH2 | Cl |
10.12 | H | CH=CH2 | CH3 |
10.13 | 炔丙基 | CH=CH2 | Cl |
10.14 | 丙二烯基 | CH=CH2 | Cl |
表11提供了14种式(Ik)化合物:
其中R1、R7和R8是如表11中所定义的。
表11
化合物编号 | R1 | R7 | R8 |
11.01 | H | C::CH | Cl |
11.02 | H | C::CH | CF3 |
11.03 | COMe | C::CH | Cl |
11.04 | H | C::CH | Br |
11.05 | COCH2OMe | C::CH | Cl |
11.06 | H | C::CSiMe3 | Cl |
11.07 | H | C::CSiMe3 | CF3 |
11.08 | H | C::CSiMe3 | Br |
11.09 | H | CH=CH2 | CF3 |
11.10 | H | CH=CH2 | Br |
11.11 | H | CH=CH2 | Cl |
11.12 | H | CH=CH2 | CH3 |
11.13 | 炔丙基 | CH=CH2 | Cl |
11.14 | 丙二烯基 | CH=CH2 | Cl |
表12提供了94种式(II)化合物,其中R2、R3、R4和R5各自是氢;n是0;且R1和R7是如表12中所定义的。
表12
化合物编号 | R1 | R7 |
12.01 | H | C::CH |
12.02 | H | C::CSiMe3 |
12.03 | H | C::CCF3 |
12.04 | H | C::CCl |
12.05 | H | CH=CH2 |
12.06 | H | CH=CF2 |
12.07 | H | CH=CCl2 |
12.08 | H | CH=CBr2 |
12.09 | H | CF=CF2 |
12.10 | H | CCl=CH2 |
12.11 | H | CF=CHF |
12.12 | H | CH=CHCF3 |
12.13 | H | CH=CClCF3 |
12.14 | H | CH2C::CH |
12.15 | H | C::CCMe3 |
12.16 | CHO | C::CMe |
12.17 | H | C::C(环丙基) |
12.18 | H | SiMe3 |
12.19 | H | C::CBr |
12.20 | H | CBr=CH2 |
12.21 | H | CH=CHSiMe3 |
12.22 | H | CH2C::CSiMe3 |
12.23 | H | C::CMe |
12.24 | H | C::CF |
12.25 | H | C::CCF2Cl |
12.26 | H | C::CCF2H |
12.27 | H | C::CCF2Br |
12.28 | H | C::CCH2F |
12.29 | H | C::CCH(Me)F |
12.30 | H | C::CC(Me)2F |
12.31 | H | C::CCH2C(Me)3 |
12.32 | H | C::CCH(Me)2 |
12.33 | H | C::CCH2CH(Me)2 |
12.34 | H | CH2C::CCMe3 |
12.35 | H | CF2C::CCMe3 |
12.36 | H | CF2C::CMe |
12.37 | H | CF2C::CH |
12.38 | H | CMe2C::CH |
12.39 | H | CHFC::CH |
12.40 | H | CHMeC::CH |
12.41 | H | CH(CF3)C::CH |
12.42 | H | C::C(1-F-环戊基) |
12.43 | H | C::CCH2OMe |
12.44 | H | C::CCMe2OMe |
12.45 | H | C::CCMe2OCOMe |
12.46 | H | C::CCF2Me |
12.47 | H | C::CC(Me)=CH2 |
12.48 | H | CH=CFCl |
12.49 | H | CH=CFBr |
12.50 | H | CH=CHBr |
12.51 | H | CH=CHF |
12.52 | H | CMe=CHCF3 |
12.53 | H | CH=CFCF3 |
12.54 | H | CH=CBrCF3 |
12.55 | H | CH=CHC2F5 |
12.56 | H | CH=CHCl |
12.57 | H | CH=C(CF3)2 |
12.58 | H | CMe=CFCl |
12.59 | H | CMe=CFBr |
12.60 | H | CMe=CF2 |
12.61 | H | CMe=CCl2 |
12.62 | H | CMe=CBr2 |
12.63 | H | CMe=CFCF3 |
12.64 | H | CMe=CClCF3 |
12.65 | H | CCF3=CF2 |
12.66 | H | CCF3=CCl2 |
12.67 | H | CCF3=CCl2 |
12.68 | H | CCF3=CCl2 |
12.69 | H | CCF3=CBr2 |
12.70 | H | CCF3=CH2 |
12.71 | H | CCF3=CFBr |
12.72 | H | CCF3=CHF |
12.73 | H | CCF3=CFCl |
12.74 | H | CCF3=CHCl |
12.75 | H | CH=CFCF2Cl |
12.76 | H | CH=CClCF2Cl |
12.77 | H | CH2CF=CF2 |
12.78 | H | CF=CFBr |
12.79 | H | CH2CH=CF2 |
12.80 | H | CH2CH=CCl2 |
12.81 | H | CH2CH=CBr2 |
12.82 | H | CCl=CF2 |
12.83 | H | C::CCH2SiMe3 |
12.84 | H | C::CSiMe2CMe3 |
12.85 | H | C::CCMe2OH |
12.86 | H | C::CCH2CH3 |
12.87 | H | C::CCF=CF2 |
12.88 | H | C::CCHFCl |
12.89 | H | CH=CFC2F5 |
12.90 | H | C::CCF2CH2CH3 |
12.91 | H | C::CCHFCH2CH3 |
12.92 | H | C::CCF(CF3)2 |
12.93 | H | CH=CClC2F5 |
12.94 | H | C::CC2F5 |
表13提供了1种式(III)化合物,其中R2、R3、R4和R5各自是氢;n是0;且Hal和R7是如表13中所定义的。
表13
化合物编号 | R7 | Hal |
13.01 | C::CH | Br |
在本说明书中,温度的单位是℃;″NMR″是指核磁共振波谱;MS代表质谱;M+-1或M++1是质谱中的信号,分别对应分子量-1或分子量+1;且″%″是重量百分比,除非对应的浓度标有其它单位。
在本说明书中使用了下面的缩写。
m.p.=熔点 b.p.=沸点
s=单峰 br=宽
d=二重峰 dd=双二重峰
t=三重峰 q=四重峰
m=多重峰 ppm=百万分之一[10-6]
表14显示了选择的熔点、选择的分子离子和选择的NMR数据,对于表1-13中的化合物,都用CDCl3作为溶剂(除非另有说明;如果使用溶剂的混合物,例如,将其表示为(CDCl3/d6-DMSO)),(在所有的情况下,都没有试图列出全部特征数据)。除非另有说明,数据涉及每种化合物的顺/反混合物。
表14
化合物编号 | 1H-NMR数据:(ppm/峰裂数/H的数目)MS-数据 | m.p./(℃) |
1.01 | 169-170 | |
1.03 | 132-135 | |
1.08 | 147-150 | |
1.10 | >200 | |
1.12 | 195-197 | |
1.13 | 139-144 | |
1.15 | 193-194 | |
1.16 | 120-125 | |
1.18 | 207-209 | |
1.19 | 210-212 | |
1.22 | 184-187 | |
1.24 | 137-141 | |
1.29 | 197-198 |
1.30 | 181-182 | |
1.32 | 173-176 | |
1.33 | 147-150 | |
1.35 | 167-169 | |
1.36 | 148-150 | |
1.38 | 156-157 | |
1.39 | 168-170 | |
1.41 | 212-213 | |
1.42 | 174-176 | |
1.50 | 117-124 | |
1.53 | 205-206 | |
1.54 | 194-195 | |
1.56 | 143-145 | |
1.57 | 118-121 | |
1.59 | 186-190 | |
1.60 | 137-139 | |
1.66 | 139-143 | |
1.67 | 406(M+-1) | 193-196 |
1.69 | 382(M+-1) | 221-223 |
1.70 | 364(M+-1) | 205-208 |
1.77 | 208-210 | |
1.78 | 202-205 | |
1.80 | 165-166 | |
1.81 | 165-169 | |
1.85 | 198-198.5 | |
1.86 | 184-184.5 | |
1.88 | 206-207 | |
1.89 | 200-201 | |
1.193 | 160-162 | |
1.94 | 205-206 | |
1.95 | 198-199 | |
1.97 | 197-198(分解) | |
1.98 | 176-177 | |
1.100 | 120-121 | |
1.101 | 128-129 | |
1.106 | 155-158 | |
1.107 | 142-143 | |
1.109 | 150-153 |
1.110 | 132-140 | |
1.137 | 132-133 | |
1.138 | 167-169 | |
1.139 | 163-165 | |
1.141 | 141-142.5 | |
1.142 | 155-156 | |
1.144 | 1.8(s,6);2.1(s,3);3.95(s,3)7.2-7.6(m,7);7.75(br.s,1);8.25(d,1) | |
1.145 | 132-141 | |
1.147 | 149-150 | |
1.150 | 143-145 | |
1.151 | 189-194 | |
1.152 | 168-170 | |
1.154 | 197-200 | |
1.155 | 174-178 | |
1.158 | 195 | |
1.166 | 172-155 | |
1.167 | 145-150 | |
1.182 | 127-129 | |
1.185 | 111-114 | |
1.194 | 2.25(s,3);3.9(s,3);6.7(t,1);7.2-7.5(m,6);7.7(s,1);7.72(br,1);8.3(d,1) | |
1.212 | 176-179 | |
1.226 | 152.5-153 | |
1.227 | 146-147 | |
1.250 | 159-162 | |
1.251 | 156-161 | |
1.252 | 163-165 | |
1.254 | 139-140 | |
1.255 | 187-187.5 | |
1.257 | 177-178 | |
2.01 | 145-148 | |
2.08 | 148-154 | |
2.66 | 160-165 | |
3.01 | 145-147 | |
3.08 | 103-105 | |
3.12 | 122-126 | |
3.18 | 160-165 |
3.29 | 146-147 | |
3.32 | 125-130 | |
3.35 | 120-126 | |
3.38 | 122-127 | |
3.41 | 169-170 | |
3.56 | 132-137 | |
3.66 | 129-133 | |
3.69 | 159-163 | |
3.97 | 133-134 | |
3.100 | 127.7-129 | |
3.109 | 117-119 | |
3.136 | 140-142 | |
3.141 | 1.55(s,6);2.7(s,3);3.4(s,3);7.2-7.3(m,4);7.4(m,1);7.5(d,2);7.55(br,1);8.3(d,1) | |
3.146 | 141-142 | |
3.157 | 145-157 | |
3.166 | 148-150 | |
3.193 | 128-132 | |
3.211 | 183-184 | |
3.250 | 140-143 | |
9.01 | 150-152 | |
9.06 | 84-86 | |
9.15 | 154-157 | |
9.21 | 185-189 | |
9.38 | 141-142 | |
9.41 | 143-145 | |
9.50 | 157-159 | |
9.53 | 133-138 | |
9.58 | 130-132 | |
9.59 | 123-125 | |
9.62 | 138-139 | |
9.65 | 164-167 | |
9.68 | 1.8(s,9);4.9+5,25(m,1);6.15-8.5(m,12) | |
9.83 | 143-145 | |
9.86 | 169-170 | |
9.89 | 167-167.5 | |
9.99 | 109-111 |
9.118 | 1.8(s,6);2.1(s,3);7.2-7.6(m,9),8.1(m,1);8.45(m,1) | |
9.132 | 162-165 | |
9.138 | 172-175 | |
9.163 | 167-171 | |
9.185 | 119-120.5 | |
9.201 | 0.0(s,9);1.55(s,2);7.0-7.3(m,8);79-8.0(m,2);8.3(m,2) | |
9.203 | 105-107 | |
12.01 | 111-115 | |
12.02 | 0.05(s,9);6.5-6.7(d+t,2);6.8-7.1(t+t,2);7.2-7.5(m,4) | |
12.03 | 262(M+H+);303(M+MeCN+H+); | |
12.04 | 92-98 | |
12.06 | 3.75(br,2);5.35(dd,1);6.75-6.9(m,2);7.1-7.2(m,2);7.35-7.5(m,4) | |
12.07 | 3.8(br,2);6.8(d,1);6.85(t,1);6.9(s,1);7.1-7.2(d+t,2);7.45-7.65(m,4) | |
12.08 | 3.8(br,2);6.7 5-6.9(m,2);7.1-7.2(m,2);7.5-7.7(m,5) | |
12.09 | 3.8(br,2);6.7-6.9(m,2);7.1-7.2(m,2);7.6(非常窄的m,4)19F:-99.7;-114.6;-177.3 | |
12.10 | 230(M+H+);371(M+MeCN+H+) | |
12.12 | 84-86 | |
12.13 | 298(M+H+);339(M+MeCN+H+); | |
12.14 | 208(M+H+);249(M+MeCN+H+); | |
12.15 | 66-69 | |
12.16 | 91-96 | |
12.17 | 0.8-0.9(m,4);1.4-1.5(m,2);3.7(br,2);6.7-6.8(m,2);7.1-7.2(m,2);7.3-7.5(m,4) | |
12.18 | 0.15(s,9);2.0-2.6(非常宽的,2);6.6-6.7(m,2);7.0-7.1(m,2);7.3-7.5(m,4) | |
12.19 | 3.8(br,2);6.75-6.9(m,2);7.1-7.2(m,2);7.35-7.55(m,4) | |
12.23 | 108-112 | |
12.25 | 3.75(br,2);6.8(m,2);7.1-7.25(m,2);7.5-7.7(m,4) |
19F:-35.9 | ||
12.26 | 3.8(br,2);6.4(t,1);6.75-6.9(m,2);7.1-7.25(m,2);7.4-7.56(m,4);19F:-105.7 | |
12.28 | 69-71 | |
12.29 | 1.7(双二重峰,3);3.8(br,2);5.5(双四重峰,1);6.75-6.9(m,2);7.05-7.2(m,2);7.4-7.6(m,4)19F:-165.6 | |
12.30 | 1.75(d,6);3.8(br,2);6.8(m,2);7.15(m,2);7.4-7.6(m,4)19F:-126.0 | |
12.32 | 1.3(d,6);3.7(br,2);6.7-6.8(d+t,2);7.15(m,2);7.3-7.5(m,4) | |
12.33 | 1.05(d,6);1.9(m,1);2.35(d,2);3.75(br,2);6.75-6.9(m,2);7.1-7.2(m,2);7.35-7.5(m,4) | |
12.42 | 1.7-2.5(m,8);3.7(br,2);6.7-6.8(m,2);7.05-7.15(m,2);7.35.7.5(m,4);7.1-7.2(m,2);7.4-7.6(m,4) | |
12.43 | 3.45(s,3);3.8(br,2);4.35(s,2);6.7-6.8(d+t,2);7.1-7.25(m,2);7.4-7.6(m,4) | |
12.45 | 1.75(s,6);2.1(s,3);3.75(br,2);6.75-6.85(m,2);7.1-7.2(m,2);7.4-7.6(m,4) | |
12.46 | 2.0(t,3);3.75(br,2);6.75-6.85(m,2);7.1-7.2(m,2);7.4-7.6(m,4) | |
12.47 | 2.0(s,3);3.75(br,2);5.3(窄的m,1);5.4(s,1);6.75-6.85(m,2);7.1-7.2(m,2);7.4-7.55(m,4) | |
12.48 | 3.8(br,2);5.85+6.45(2ds,1);6.7-6.9(m,2);7,1-7.2(m,2);7.4-7.65(m,4);19F:-71.2;-73.9 | |
12.49 | 4.0-4.6(br,2);6.0+6.7(2ds,1);6.75-6.9(m,2);7,1-7.2(m,2);7.4-7.65(m,4); | |
12.50 | 86-92 | |
12.53 | ||
12.58 | 2.1(2s,3);3.8(br,2);6.7-6.9(m,2);7.1-7.2(m,2);7.35-7.5(m,2);19F:-80.1;-81.3 | |
12.59 | 2.1(2s,3);3.8(br,2);6.7-6.9(m,2);7.1-7.2(m,2);7.35-7.5(m,2);19F:-74.2;-74.6 | |
12.62 | 120-129 |
12.70 | 3.75(br,2);5.8(窄的m,1);5.95(窄的m,1);6.75-6.9(m,2);7.1-7.2(m,2);7.4-7.55(m,4) | |
12.75 | 67-68.5 | |
12.83 | 0.0(s,9);1.6(s,2);6.6(d,1);6.65(t,1);7.0(m,2);7.2-7.4(m,4) | |
12.84 | 0.0(s,6);0.8(s,9);4.25(非常宽,2);6.65-6.75(m,2);6.9-7.05(m,2);7.2-7.4(m,4) | |
12.85 | 252(M+H+) | |
15.25 | 131-134 | |
15.26 | 无定形的 | |
15.28 | 1.3(s,9);7.2-7.5(m,10);8.1(m,2);8.45(m,2) | |
16.7 | 63-64 |
表15提供了48种式1(m)化合物,其中R、X和Het是如表15中所定义的。
表15
化合物编号 | X | R | Het |
15.1 | H | C::CH | Het(1) |
15.2 | H | C::CH | Het(2) |
15.3 | H | C::CH | Het(3) |
15.4 | H | C::CH | Het(4) |
15.5 | Cl | C::CH | Het(1) |
15.6 | Cl | C::CH | Het(2) |
15.7 | Cl | C::CH | Het(3) |
15.8 | Cl | C::CH | Het(4) |
15.9 | F | C::CH | Het(1) |
15.10 | F | C::CH | Het(2) |
15.11 | F | C::CH | Het(3) |
15.12 | F | C::CH | Het(4) |
15.13 | H | C::CMe | Het(1) |
15.14 | H | C::CMe | Het(2) |
15.15 | H | C::CMe | Het(3) |
15.16 | H | C::CMe | Het(4) |
15.17 | F | C::CMe | Het(1) |
15.18 | F | C::CMe | Het(2) |
15.19 | F | C::CMe | Het(3) |
15.20 | F | C::CMe | Het(4) |
15.21 | Cl | C::CMe | Het(1) |
15.22 | Cl | C::CMe | Het(2) |
15.23 | Cl | C::CMe | Het(3) |
15.24 | Cl | C::CMe | Het(4) |
15.25 | H | C::CCMe3 | Het(1) |
15.26 | H | C::CCMe3 | Het(2) |
15.27 | H | C::CCMe3 | Het(3) |
15.28 | H | C::CCMe3 | Het(4) |
15.29 | Cl | C::CCMe3 | Het(1) |
15.30 | Cl | C::CCMe3 | Het(2) |
15.31 | Cl | C::CCMe3 | Het(3) |
15.32 | Cl | C::CCMe3 | Het(4) |
15.33 | F | C::CCMe3 | Het(1) |
15.34 | F | C::CCMe3 | Het(2) |
15.35 | F | C::CCMe3 | Het(3) |
15.36 | F | C::CCMe3 | Het(4) |
15.37 | H | CH=CClCF3 | Het(1) |
15.38 | H | CH=CClCF3 | Het(2) |
15.39 | H | CH=CClCF3 | Het(3) |
15.40 | H | CH=CClCF3 | Het(4) |
15.41 | Cl | CH=CClCF3 | Het(1) |
15.42 | Cl | CH=CClCF3 | Het(2) |
15.43 | Cl | CH=CClCF3 | Het(3) |
15.44 | Cl | CH=CClCF3 | Het(4) |
15.45 | F | CH=CClCF3 | Het(1) |
15.46 | F | CH=CClCF3 | Het(2) |
15.47 | F | CH=CClCF3 | Het(3) |
15.48 | F | CH=CClCF3 | Het(4) |
表16提供了12种式II(m)化合物,其中R和X是如表16中所定义的。
表16
化合物编号 | X | R |
16.1 | H | C::CH |
16.2 | Cl | C::CH |
16.3 | F | C::CH |
16.4 | H | C::CMe |
16.5 | F | C::CMe |
16.6 | Cl | C::CMe |
16.7 | H | C::CCMe3 |
16.8 | Cl | C::CCMe3 |
16.9 | F | C::CCMe3 |
16.10 | H | CH=CClCF3 |
16.11 | Cl | CH=CClCF3 |
16.12 | F | CH=CClCF3 |
根据下面的反应方案,可以制备出根据本发明的化合物,其中除非另有说明,每个变量的定义是如上面对式(I)化合物的定义。
有许多制备式(I)化合物的替代方法。
方法A
式(I)化合物可以如下制备:在存在强碱[例如NaH或六甲基二硅氮烷钠]的情况下,在无水极性溶剂[优选THF]中,在-10℃至溶剂沸点之间的温度[优选在环境温度下],使式(II)化合物与式Het-C(=O)OR’[其中R’是C1-5烷基]化合物反应。J.Wang等,Synlett2001,1485的文章详述了类似的制备。
方法B
式(I)化合物可以如下制备:在惰性有机溶剂[例如醋酸乙酯、二氯甲烷、二噁烷或DMF]中,在-10℃至溶剂沸点之间的温度[优选在环境温度下],使式(II)化合物与式Het-C(=O)R”[其中R”是OH或离去基团,例如Cl、Br、F或OC(=O)C1-4烷基]化合物反应。如果R”是OH,则在存在激活剂[例如BOP-Cl]和2当量的碱[例如叔胺、无机碳酸盐或碳酸氢盐]的情况下进行反应。或者,如果R”是离去基团,则在存在至少1当量的碱[例如吡啶、叔胺、无机碳酸盐或碳酸氢盐]的情况下进行反应。
方法C
式(I)化合物[其中R1是如上所定义的,但不是氢]可以如下制备:在存在碱[例如叔胺、碱金属碳酸盐、碱金属碳酸氢盐、碱金属氢氧化物或NaH;尽管如果L1是O(CO)C1-4烷基,则在没有碱的情况下简单地加热也是可行的]的情况下,在溶剂[例如卤化的溶剂(例如二氯甲烷)、醚、醋酸乙酯、DMF或甚至水(作为两相混合物,任选地存在相转移催化剂,例如硫酸氢叔丁基铵)]中,使式(I)化合物[其中R1是氢]与式R1-L1[其中R1是如上所定义的,但不是氢;且L1是离去基团例如Cl、Br、I、磺酸盐(例如甲磺酸盐或甲苯磺酸盐)或OC(O)C1-4烷基]化合物反应。
方法D
式(I)化合物可以如下制备:在存在Cu(I)化合物和疏质子溶剂[例如环醚、例如二噁烷]的情况下,在高温、且优选地在回流下,使式(III)化合物[其中Hal优选地是溴或碘]与式Het-C(=O)NH2化合物反应。优选的条件是:在存在作为配体形成物的1,2-二胺(例如1,2-二氨基环己烷或亚乙基二胺)和至少1当量碱(例如碱金属碳酸盐或碱金属磷酸盐)的情况下,相对于式(III)化合物,以2%-100%mol/mol使用的CuI。A.Klapars等J.Am.Chem.Soc.
123,7727(2001)的文章详述了类似的制备。
方法E
通过转化式(IV)化合物,可以制备出式(I)化合物:
[其中FG是官能团,其可以经1步或多步合成步骤转化成R7]。官能团的相互转换对于本领域的技术人员而言是标准方法。文献记载了许多方法,其可以原样使用,或者根据存在的官能性进行改进;表A提供了参考文献(其中的一些还引用了其它的合适的文献),其特别与通过FG和R7的相互转换制备式(I)化合物有关。本领域的技术人员能够明白,表A提供的文献实例未必仅限于具体提到的R7的制备,而是也可以类似地用于制备其它的结构上相关的R7。
表A
参考文献 | FG | R7 |
Synthesis 2001,2081Tetrahedron 58,1491(2002) | CHO | CH=CBr2CH=CHBrC::CBr |
Russ.Chem.Bull.50(6),1047(2001) | CHO | CH=CCl2 |
Tetrahedron 57,7519(2001) | CHO | CH=CClCF3CH=CFCF2Cl |
Bull.Chem.Soc.Jpn.73,1691(2000)Bull.Chem.Soc.Jpn.71,2903(1998-) | CHO | CF=CBrF |
J.Chem.Soc.Perkin 1 2002,883 | COCH3 | C(CH3)=CHBrC(CH3)=CCl2 |
J.Fluorine Chem.1,381(1972)J.Fluorine Chem.23,339(1983) | COCH3COCF3 | C(CH3)=CBr2C(CH3)=CFBrC(CH3)=CFClC(CF3)=CFBrC(CF3)=CFClC(CF3)=CF2 |
Tetrahedron Letters 41,8045(2000)J.Org.Chem.62,9217(1997) | 卤素 | CF=CHF |
Tetrahedron Letters 37,8799(1996) | 卤素 | CH=CF2 |
JP 09278688J.Fluorine Chem.31,115(1986) | 卤素 | CF=CF2 |
Zh.Org.Khim.25,1451(1989) | 卤素 | CF=CFCl |
J.Org.Chem.53,2714(1988) | 卤素 | CF=CFCF3 |
J.Org.Chem.56,7336(1991)Tetrahedron Letters 42,4083(2001) | 卤素 | C(CF3)=CH2 |
Ukr.Khim.Zh.32,996(1966) | CHBrCH2CF3 | CH=CHCF3 |
Bull.Chem.Soc.Jap.62,1352 | CH=CClCF3CH=CFCF2Cl | C::CCF3C::CCF2Cl |
J.Org.Chem.54,5856(1989)J.Am.Chem.Soc.109,2138(1987)Tetrahedron 45,6511(1989)J.Orgmet.Chem.549,127(1997)Tetrahedron 56,10075(2000)Tetrahedron Asymmetry 6,245(1995) | 卤素或三氟甲基磺酸盐 | C::CHC::CSiMe3C::CCH3C::CCMe3C::CCH2OHC::CCHMeOHC::CCMe2OHC::CCHOC::CC(O)Me |
J.Org.Chem.32,1674(1967) | C::CCH3 | CH2C::CH |
Synth.Comm.1989,561 | CHOCH2CHO | C::CHCH2C::CH |
WO 01 092563 | CHO | CH=CH2 |
J.Am.Chem.Soc.123,4155(2001)Org.Lett.2,3703(2000)J.Org.Chem.57,3558(1992) | 卤素或三氟甲基磺酸盐 | CH=CH2 |
Synthesis 2001,893 | ||
GB 2 183 639 | C::CH | CH=CH2 |
Synthesis 1996,1494J.Org.Chem.49,294(1984) | CHO | C::CClC::CHC::CBr |
US 6 159956 | CH2Br | CH2CF=CF2 |
Liebigs Ann.Chem.1995,2027 | CH2Br | CH=C(CF3)2 |
J.Am.Chem.Soc.123,4155(2001) | CH2Br | CH2C::CSiMe3 |
Inorg.Chim.Acta 296,37(1999) | 卤素 | CH2C::CMe3 |
J.Fluorine Chem.111,185(2001)J.Chem.Soc.Perkin I 1988,921 | CH=CHBrCH=CFBrCH=CBr2 | CH=CHCF3CH=CFCF3CH=C(CF3)2 |
DE 4417441US3976691J.Org.Chem.64,7048(1999) | C::CCH2OHC::CCHMeOHC::CCMe2OHC::CCHOC::CC(O)Me | C::CCH2FC::CCHMeFC::CCMe2FC::CCHF2C::CCF2Me |
J.Chem.Soc.Perkin I 1994,725 | C::CCH2OH | C::CCH2CF3 |
Synthesis 1997,1489Angew.Chem.Int.Ed.39,2481(2000)J.Org.Chem.47,2255(1982)J.Fluorine.Chem.113,55(2002) | C::CH | C::CCF2CF3CH=CHCF2CF3 |
J.Fluorine.Chem.64,61(1993)J.Am.Chem.Soc.109,3492(1987) | C::CH | C::CCHFClC::CCF2Br |
J.Am.Chem.Soc.107,5186(1985) | CH=CHBr | CH=CHCF2CF3 |
有许多制备式(II)、(III)或(IV)化合物的替代方法。
方法F-式(II)或(III)化合物的制备
通过官能团相互转换,可以从式(V)化合物[其中FG是如上对式(IV)化合物所定义的,且T是卤素、氨基、NHR1、保护的氨基T’(例如氨基甲酸酯、酰胺、环状酰亚胺、N-烷基-、N-链烯基-、N-苄基-、N-二苯基甲基-或N-三苯甲基-衍生物、亚胺衍生物或N-甲硅烷基-或N-二甲硅烷基-衍生物)或基团T”(也就是说,可以通过使用文献所述的合成方法转化成NH2或NHR1的基团;T”优选地为叠氮基、硝基、卤素、三氟甲基磺酸盐、CONH2、COOH、COCl或NCO)]制备出式(II)、(III)或(VI)化合物。从式(V)化合物开始,通过使用与上面方法E类似的方法,可以将官能团FG转化成R7。该转化直接产生式(II)化合物[当T是NHR1时]、式(III)化合物[当T是卤素(优选氯、溴或碘)时]或式(VI)化合物[当T是T’或T”时]。
在第二步中,通过使用总体上如上所述的方法[也就是说,去保护或将T”转化成NH2],可以将式(VI)或(II)的化合物[当R1不是H时]转化成式(II)化合物[其中R1是H]。
T’的通用值的实例和去保护的方法参见T.W.Green和P.Wuts,Protective Groups in Organic Synthesis,第3版(John Wiley&Sons 1999),第7章。
T”的有用值的汇编和将T”转化成NH2、T’或NHR1的文献可参见M.B.Smith,Compendium of Organic Synthetic Methods,Vols.1-10,第7章(Wiley,Vol.10:2002。
方法G
通过式(VII)化合物和式(VIII)化合物之间的偶联反应[其中Ra和Ra’各自独立地为卤素(优选Cl、Br或I),三氟甲基磺酸盐或含有金属的官能团,其含有例如B、Sn、Mg、Zn或Cu作为金属;实例是B(OH)2、硼酸的酯(优选源自1,2-或1,3-二元醇的酯)、三烷基锡(优选Sn(CH3)3或Sn(nBu)3)、Mg的卤素盐、Zn或Cu的卤素盐。如果Ra或Ra’是含有金属的官能团,其它的取代基必然是卤素或三氟甲基磺酸盐],可以制备出式(II)、(III)或(VI)的化合物。
这样的偶联反应是文献中广泛知道的。特别合适的是Pd(0)、Ni(0)或铜催化的偶联,其是本领域的技术人员熟知的,例如Stille偶联、Suzuki偶联、Negishi偶联或Ullmann反应。关于这些反应的综述可参见Metal-Catalysed Cross-Coupling Reactions;F.Diederich和P.Stang(编);Wiley-VCH;Weinheim 1998。
在第二步中,通过上面一般地描述的方法[也就是说,去保护或T”向NH2的转化],可以将式(VI)或(II)的化合物[当R1不是H时]转化成式(II)化合物[其中R1是H]。
现在已经惊奇地发现,为了实践的目的,新的式(I)化合物在保护植物免受真菌、细菌和病毒造成的病害方面具有非常有利的活性范围。
式(I)化合物可以作为控制植物害虫的活性成分用于农业领域和相关的应用领域。新的化合物的特征是:在较低的施用率具有优异的活性,植物能充分耐受,和对环境安全。它们具有非常有用的治病、预防和系统特性,且用于保护多种栽培的植物。式I化合物可以用于抑制或破坏发生在不同种类的有用植物或植物部分(果实、花朵、叶子、茎、块茎、根)上的害虫,同时还保护随后生长的植物的那些部分,例如免受致植物病微生物的侵害。
还可以使用式(I)化合物作为敷裹剂,用于处理植物繁殖材料、特别是种子(果实、块茎、谷粒)和植物插条(例如稻谷),以避免真菌感染和抵抗在土壤中出现的致植物病真菌。
而且,根据本发明的化合物可以在相关领域中用于控制真菌,例如在技术材料(包括木材和与木材有关的技术产品)的保护、食品储藏、卫生管理等方面。
式(I)化合物对例如下述种类的致植物病真菌是有效的:半知菌(例如灰葡萄孢、稻瘟病菌、长蠕孢、镰孢菌、颖枯壳针孢、落花生尾孢和交链孢霉)和担子菌类(例如丝核菌属、锈病菌属、柄锈菌属)。另外,它们对于子囊菌纲(例如黑星菌属和白粉菌属、柄球菌属、链核盘菌属、钩丝壳霉属)和卵菌纲(例如疫霉属、腐霉属、单轴霉属)也是有效的。对白粉病(白粉菌属)和锈病(柄锈菌属)观察到了显著的活性。而且,新的式I化合物对致植物病细菌和病毒(例如对黄单胞菌属数种、假单胞菌属数种、梨火疫病菌和烟草花叶病毒)也是有效的。
在本发明的范围内,要保护的目标作物典型地包括下述的植物物种: 谷物(小麦、大麦、黑麦、燕麦、稻谷、玉米、高粱和有关的物种);甜菜(糖甜菜和饲料甜菜);梨果、核果和软果(苹果、梨、李子、桃子、扁桃、樱桃、草莓、树莓和黑莓);豆科植物(豆类、扁豆、豌豆、大豆);油料植物(油菜、芥子、罂粟、橄榄、向日葵、椰子、蓖麻、可可豆、落花生);黄瓜类植物(南瓜、黄瓜、西瓜);纤维植物(棉花、亚麻、大麻、黄麻);柑橘类水果(橙子、柠檬、葡糖柚、桔子);蔬菜(菠菜、莴苣、芦笋、甘蓝、胡萝卜、洋葱、番茄、马铃薯、辣椒);樟科(鳄梨、樟脑属、樟脑)或其它植物,例如烟草、坚果、咖啡、茄子、甘蔗、茶树、胡椒、藤本植物、蛇麻草、香蕉和天然橡胶树、以及观赏植物。
式(I)化合物以未修饰的形式使用或者,优选地,与制剂领域中常规采用的辅料一起使用。为此目的,它们常规地以已知的方式制成可乳化的浓缩物、可涂布的膏剂、可直接喷雾的或可稀释的溶液、稀乳化液、可润湿的粉末、可溶的粉末、粉剂、颗粒和包囊剂,例如在聚合物中。根据组合物的类型,根据预期的目的和主要环境,选择施用方法例如喷射、雾化、粉化、散射、涂布或灌注。组合物还可以含有其它的辅料,例如稳定剂、消泡剂、粘度调节剂、粘合剂或胶粘剂、肥料、微量营养素供体或用于达到特定效果的其它制剂。
合适的载体和辅料可以是固体或液体,且是制剂技术中使用的物质,例如天然的或再生的矿物质、溶剂、分散剂、润湿剂、胶粘剂、增稠剂、粘合剂或肥料等。这样的载体记载在例如WO 97/33890中。
式(I)化合物通常以组合物的形式使用,且可以与其它化合物同时或先后应用于要处理的作物区域或植物。这些其它的化合物可以是例如肥料或微量营养素供体或能影响植物生长的其它制品。它们还可以是选择性的除草剂和杀虫剂、杀真菌剂、杀菌剂、杀线虫剂、杀软体动物剂或这些制剂中的几种的混合物,如果需要,则与制剂领域中常用的其它载体、表面活性剂或应用促进辅料一起使用。
式(I)化合物可以与其它的杀真菌剂混合,在有些情况下会产生意外的协同活性。特别优选的混合组分是唑类,例如戊环唑、BAY14120、双苯三唑醇、糠菌唑、环唑醇、噁醚唑、烯唑醇、氧唑菌、腈苯唑、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、酰胺唑、环戊唑醇、环戊唑菌、腈菌唑、稻瘟酯、戊菌唑、啶斑肟、丙氯灵、丙环唑、simeconazole、戊唑醇、氟醚唑、三唑酮、唑菌醇、氟菌唑、戊叉唑菌;嘧啶基甲醇类,例如嘧啶醇、异嘧菌醇、氟苯嘧啶醇;2-氨基嘧啶类,例如磺嘧菌灵、甲菌定、乙菌定;吗啉类,例如吗菌灵、苯锈啶、丁苯吗啉、螺噁茂胺、克啉菌;苯氨基嘧啶类,例如环丙嘧啶、嘧菌胺、二甲嘧菌胺;吡咯类,例如拌种咯、氟噁菌;苯基酰胺类,例如苯霜灵、呋氨丙灵、甲霜灵、R-甲霜灵、甲呋酰胺、噁霜灵;苯并咪唑类,例如苯菌灵、多菌灵、双乙氧咪唑威、麦穗宁、涕必灵;二酰胺类,例如乙菌利、菌核利、异丙定、甲菌利、杀菌利、烯菌酮;酰胺类,例如萎锈灵、呋菌胺、氟酰胺、丙氧灭锈胺、氧化萎锈灵、溴氟唑菌;胍类,例如双胍盐、多果定、iminoctadine;strobilurines,例如腈嘧菌酯、亚胺菌、叉氨苯酰胺、SSF-129、trifloxystrobin、picoxystrobin、BAS 500F(建议名pyraclostrobin)、BAS 520;二硫代氨基甲酸类,例如福美铁、代森锰锌、代森锰、代森联、甲基代森锌、福美双、代森锌、福美锌;N-卤素甲硫基邻苯二甲酰亚胺类,例如敌菌丹、克菌丹、抑菌灵、氟菌安、灭菌丹、对甲抑菌灵;铜化合物,例如波尔多液、氢氧化铜、王铜、硫酸铜、氧化亚铜、锰铜混剂、喹啉铜;硝基苯酚衍生物,例如敌螨普、异丙消;有机磷衍生物,例如克瘟散、异稻瘟净、稻瘟灵、双氟苯磷、定菌磷、甲基立枯磷;其他,例如acibenzolar-S-methyl、敌菌灵、benthiavalicarb、灭瘟素、灭螨猛、地茂散、百菌清、cyflufenamid、清菌脲、二氯萘醌、哒菌清、氯硝胺、乙霉威、烯酰吗啉、SYP-L190(建议名flumorph)、二噻农、ethaboxam、氯唑灵、噁唑酮菌、fenamidone、fenoxanil、三苯锡基、嘧菌腙、氟啶胺、磺菌胺、fenhexamid、藻菌磷、土菌消、iproValicarb、IKF-916(cyazofamid)、春雷霉素、磺菌威、metrafenone、nicobifen、戊菌隆、四氯苯酞、多氧霉素、噻菌灵、百维灵、咯喹酮、喹氧灵、五氯硝基苯、硫、唑菌嗪、三环唑、嗪氨灵、有效霉素、zoxamide(RH7281)。
优选的施用式(I)化合物或含有至少一种所述化合物的农用化学组合物的方法是叶片施用。施用频率和施用率取决于被相应病原菌侵染的风险。但是,通过用液体制剂浸泡植物所在地,或通过向土壤中施用固体形式的化合物,例如以颗粒形式(土壤施用),式I化合物也可以经过土壤从根部渗入植物(系统作用)。在水稻作物中,可以将这样的颗粒施用到灌溉的稻田中。通过用杀真菌剂的液体制剂浸泡种子或块茎,或用固体制剂涂布它们,还可以将式I化合物施用于种子(包衣)。
以已知的方式制备制剂[也就是说,含有式(I)化合物的组合物]和需要时含有固体或液体辅料,典型地通过将化合物与补充剂一起均匀混合和/或研磨,补充剂是例如溶剂、固体载体和任选的表面活性化合物(表面活性剂)。
农用化学制剂通常含有0.1-99重量%、优选0.1-95重量%的式I化合物、99.9-1重量%、优选99.8-5重量%的固体或液体辅料和0-25重量%、优选0.1-25重量%的表面活性剂。
有利的施用率通常是5g-2kg活性成分(a.i.)/公顷(ha)、优选10g-1kg a.i./ha、最优选20g-600g a.i./ha。当用作种子浸泡剂时,方便的剂量是10mg-1g活性物质/kg种子。
尽管优选地将商业产品配制成浓缩物,但终端用户一般使用稀制剂。
下面的非限制性的实施例更详细地说明了上述的发明。
实施例1
该实施例说明了化合物编号1.01的制备。
在冰冷却下,使2-氨基-4’-乙炔基-联苯(0.30g)和1-甲基-3-三氟甲基-4-氯羰基-吡唑(0.33g)在THF中混合,然后加入吡啶(0.12ml)。升至环境温度后,将悬浮液搅拌3.5小时,倒入水中,并用醋酸乙酯萃取2次。分离有机相,用硫酸钠干燥,蒸发溶剂,并在硅胶上进行色谱纯化(溶剂:己烷∶醋酸乙酯2∶1),生成0.4g(70.2%)化合物编号1.01。
实施例2
该实施例说明了化合物编号2.01的制备。
向溶解在10ml二氯甲烷中的1-甲基-3-三氟甲基-4-吡咯羧酸(0.22g)中,加入三乙胺(0.32ml)和2-氨基-4’-三甲基甲硅烷基乙炔基-联苯(0.3g),最后,在冰冷却下,加入二(2-氧代-3-噁唑烷基)氯代次膦酸(0.29g)。搅拌18小时后,在减压下去除溶剂,将残余物用醋酸乙酯处理。用水和盐水洗涤,经硫酸钠干燥,蒸发溶剂,生成0.45g黄色油,在硅胶上进行色谱(洗脱剂:己烷∶醋酸乙酯2∶1),生成0.13g(26%)化合物编号2.01。
实施例3
该实施例说明了化合物编号1.72的制备。
在0-5℃,向在5ml无水THF中的NaH(46mg)中,加入在10ml无水THF中的2-N-甲酰基氨基-4’-(丙炔-1-基)-联苯(0.3g)。在该温度反应1小时,然后加入1-甲基-3-三氟甲基-4-氯羰基-吡唑(0.372g)。将得到的悬浮液在室温搅拌过夜,倒入盐水中,用醋酸乙酯萃取。蒸发溶剂,将残余物放入甲醇中,并加入甲醇钠(10mg)。30分钟后,用稀HCl中和混合物,用醋酸乙酯萃取,并洗涤至中性。在硅胶上进行色谱纯化(洗脱剂:醋酸乙酯∶己烷1∶2),在甲苯∶己烷(4∶1)中重结晶,生成0.169g化合物编号1.72。
实施例4
该实施例说明了使用上面的方法F制备2-氨基-4’-(三甲基甲硅烷基)乙炔基-联苯(化合物编号12.02)和2-氨基-4’-乙炔基-联苯(化合物编号12.01)。
在氮气下,向在哌啶(25ml)中的2.5g 2-氨基-4’-溴-联苯(WO0264562)中,依次加入CuI(0.1g)、二(三苯基膦基)钯二氯化物(0.35g)和三甲基甲硅烷基乙炔(2.8ml)。将混合物在室温搅拌22小时,再在60℃搅拌26小时。冷却后,用水稀释反应混合物,用醋酸乙酯萃取。然后用水洗涤有机相,经硫酸钠干燥。真空蒸发溶剂后,在硅胶上色谱纯化混合物(己烷∶醋酸乙酯9∶1),生成2-氨基-4’-(三甲基甲硅烷基)乙炔基-联苯(2g)(化合物编号12.02)。
将1.4g该化合物溶解到甲醇(40ml)中,冷却下加入碳酸钾(0.9g)。将得到的悬浮液搅拌2小时,倒在冰-水上,滤出形成的沉淀,用水彻底洗涤,并干燥,得到2-氨基-4’-乙炔基-联苯(0.9g)(化合物编号12.01)的浅褐色晶体。
实施例5
该实施例说明了2-N-甲酰基氨基-4’-(丙炔-1-基)-联苯(化合物编号12.16)的制备。
在氮气下,使N-甲酰基氨基-4’-溴-联苯(3.5g)(J.Chem.Soc.1957,4)、三丁基锡(丙炔基-1)(5g)(购自Aldrich)、四(三苯基膦)钯(0.37g)在甲苯(200ml)中混合,加热回流16小时。用水稀释得到的黑色混合物,用醋酸乙酯萃取。用水洗涤有机相,经硫酸钠干燥,在减压下蒸发溶剂。将残余物放入乙腈中,用己烷反复洗涤。在减压下去除乙腈后,将残余物在硅胶上进行色谱(洗脱剂:己烷醋酸乙酯2∶1),得到2-N-甲酰基氨基-4’-(丙炔-1-基)-联苯(化合物编号12.16)(1.57g)的浅黄色粉末。
实施例6
该实施例说明了2-氨基-4’(2,2-二氯)亚乙基-联苯(化合物编号12.07)和2-氨基-4’(氯乙炔基)-联苯(化合物编号12.04)的制备。
a)2-硝基-4’(2,2-二氯)亚乙基-联苯的制备
向在乙醇(70ml)中的2-硝基-4’甲酰基-联苯(2g)(WO 9503290)(通过Pd-催化的2-溴硝基苯与4-甲酰基-苯基-硼酸的偶联制备)中,加入水合肼(95%)(1.32g),然后将得到的混合物回流5小时。在减压下蒸发溶剂至干,将残余物悬浮到DMSO(30ml)中,然后依次加入氨(25%)(3ml)和新制备的CuCl(80mg),最后在水冷却下滴加四氯化碳(3.8g)。将混合物在室温搅拌24小时,将得到的绿色悬浮液倒入水中,用二氯甲烷萃取,用水洗涤,并经硫酸钠干燥。蒸发溶剂,将残余物在硅胶上色谱纯化(洗脱剂:己烷∶醋酸乙酯4∶1),生成2-硝基-4’(2,2-二氯)亚乙基-联苯(0.8g),m.p.58-59℃。
b)2-氨基-4’(2,2-二氯)亚乙基-联苯的制备
将步骤(a)的2-硝基-4’(2,2-二氯)亚乙基-联苯(0.76g)溶解到50%乙醇(30ml)中,加热回流。然后滴加在50%乙醇(10ml)中的2N HCl(0.3ml)。将反应混合物回流4小时,冷却至室温,过滤。用碳酸氢钠中和滤液,用醋酸乙酯萃取2次,有机相经硫酸钠干燥。在减压下蒸发溶剂,生成2-氨基-4’(2,2-二氯)亚乙基-联苯(0.62g)(化合物编号12.07)。
c)将2-氨基-4’(2,2-二氯)亚乙基-联苯(3g)溶解到150ml已经悬浮有0.9g KOH(85%,粉末)的二甲基亚砜中。将混合物在室温搅拌过夜,用过量的水稀释,用醋酸乙酯萃取2次,有机相经硫酸钠干燥。在减压下蒸发溶剂,将残余物在硅胶上色谱纯化(洗脱剂:己烷∶醋酸乙酯4∶1),生成2.5g 2-氨基-4’(2,2-二氯)亚乙基-联苯的褐色固体。
实施例7
该实施例说明了化合物编号12.18的制备。
步骤A:2-硝基-(4’-三甲基甲硅烷基)-联苯
将2-溴-硝基苯(0.86g)、4-(三甲基甲硅烷基)苯基硼酸(1g)和二-(三苯基膦)-钯二氯化物(0.3g)溶解到二甲氧基乙烷(35ml)中,然后逐滴加入溶解在水(5ml)中的碳酸氢钠(1.3g)溶液。将混合物加热3小时(80℃浴温),冷却至室温,倒在醋酸乙酯∶水1∶1(300ml)上,抽滤。分离有机相,经硫酸钠干燥,去除溶剂。将得到的残余物(1.58g黑色油)在硅胶上色谱纯化(洗脱剂:己烷∶醋酸乙酯4∶1),生成黄色油(1.12g)。该化合物用在步骤B中。
步骤B:
2-氨基-(4’-三甲基甲硅烷基)-联苯[化合物12.18]
将从上面步骤A得到的化合物(0.955g)和甲酸铵(1.86g)溶解到甲醇(30ml)中,用氮气吹洗。向该溶液中,分2次加入Pd(100mg;10%碳载)。在室温搅拌15小时后,过滤反应混合物,蒸发溶剂。
式(I)化合物的制剂实施例
制备式I化合物的制剂,例如可乳化的浓缩物、溶液、颗粒、粉剂和可润湿的粉末的操作方法记载在WO97/33890中。
生物学实施例:杀真菌作用
实施例B-1:对小麦上的隐匿柄锈菌(小麦褐锈病)的作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理1周龄的小麦植株cv.Arina。施用1天后,通过向试验植株上喷射孢子悬浮液(1×105夏孢子/ml)来接种小麦植株。在20℃和95%相对湿度下保温培养2天后,将植株在20℃和60%相对湿度的温室中保持8天。接种后10天,评定病害发生率。
使用每种化合物1.01、1.03、1.08、1.10、1.12、1.13、1.15、1.16、1.18、1.19、1.22、1.24、1.33、1.56、1.57、1.60、1.66、1.67、1.69、1.70、1.77、1.78、1.81、1.106、1.107、1.138、1.139、1.151、1.152、1.154、1.155、1.182、1.185、1.251、1.252、2.01、2.08、2.66、3.01、3.08、3.12、3.18、3.32、3.56、3.66、3.69、3.250、9.01、9.06、9.15、9.21、9.41、9.50、9.53、9.59、15.25、15.26和15.28,实际上彻底预防了侵染(0-5%侵染)。
实施例B-2:对苹果上的白粉病柄球菌(苹果白粉病)的作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理5周龄的苹果幼苗cv.McIntosh。施用1天后,通过在试验植株上方摇动感染了苹果白粉病的植株来接种苹果植株。在22℃和60%相对湿度、14/10小时(光照/黑暗)的光照方式下保温培养12天后,评定病害发生率。
使用每种化合物1.01、1.03、1.08、1.10、1.12、1.13、1.15、1.16、1.18、1.19、1.24、1.33、1.35、1.36、1.56、1.57、1.66、1.67、1.70、1.77、1.78、1.81、1.106、1.107、1.139、1.151、1.152、1.154、1.155、1.182、1.185、1.251、1.252、2.01、2.08、2.66、3.01、3.08、3.12、3.18、3.32、3.35、3.56、3.66、3.69、3.250、9.01、9.06、9.15、9.21、9.41、9.50、9.53、9.59、9.62、15.25、15.26和15.28,实际上彻底预防了侵染(0-5%侵染)。
实施例B-3:对苹果上的苹果黑星菌(苹果黑星病)的作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理4周龄的苹果幼苗cv.McIntosh。施用1天后,通过给试验植株喷洒孢子悬浮液(4×105分生孢子/ml)来接种苹果植株。在21℃和95%相对湿度保温培养4天后,将植株置于21℃和60%相对湿度的温室中4天。在21℃和95%相对湿度另外保温培养4天后,评定病害发生率。
使用每种化合物1.01、1.03、1.08、1.10、1.12、1.13、1.18、1.19、1.24、1.33、1.56、1.57、1.66、1.67、1.69、1.70、1.77、1.78、1.81、1.106、1.107、1.138、1.152、1.154、1.155、1.251、1.252、2.01、2.08、2.66、3.01、3.08、3.12、3.18、3.32、3.56、3.66、3.69、9.01、9.06、9.15、9.21、9.50和9.59,实际上彻底预防了侵染(0-5%侵染)。
实施例B-4:对大麦上的禾白粉菌(大麦白粉病)的作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理1周龄的大麦植株cv.Regina。施用1天后,通过在试验植株上方摇动感染了白粉病的植株来接种大麦植株。在20℃/18℃(日/夜)和60%相对湿度的温室中保温培养6天后,评定病害发生率。
使用每种化合物1.01、1.03、1.08、1.10、1.12、1.13、1.15、1.16、1.18、1.19、1.24、1.33、1.35、1.36、1.56、1.57、1.66、1.67、1.70、1.77、1.78、1.106、1.107、1.152、1.155、1.251、1.252、2.01、2.08、2.66、3.01、3.08、3.12、3.18、3.32、3.35、3.56、3.66、3.69、3.250、9.01、9.06、9.15、9.21、9.41、9.50和9.59,实际上彻底预防了侵染(0-5%侵染)。
实施例B-5:对葡萄上的灰葡萄孢(葡萄灰霉病)的作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理5周龄的葡萄秧苗cv.Gutedel。施用2天后,通过向试验植株上喷洒孢子悬浮液(1×106分生孢子/ml)来接种葡萄植株。在21℃和95%相对湿度的温室中保温培养4天后,评定病害发生率。
使用每种化合物1.01、1.03、1.08和1.10,实际上彻底预防了侵染(0-5%侵染)。
实施例B-6:对番茄上的灰葡萄孢(番茄灰霉病)的作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理4周龄的番茄植株cv.Roter Gnom。施用2天后,通过向试验植株上喷洒孢子悬浮液(1×105分生孢子/ml)来接种番茄植株。在20℃和95%相对湿度的生长室中保温培养4天后,评定病害发生率。
使用每种化合物1.01、1.03、1.08、1.10、1.12、1.13、1.15、1.16、1.18、1.19、1.24、1.33、1.36、1.56、1.57、1.66、1.67、1.69、1.70、1.77、1.78、1.106、1.107、1.138、1.139、1.152、1.155、1.251、1.252、2.01、2.66、3.01、3.08、3.12、3.66、3.69、3.250、9.06、9.15、9.21、9.41、9.50和9.59,实际上彻底预防了侵染(0-5%侵染)。
实施例B-7:对小麦上的颖枯壳针孢(小麦颖枯病菌叶斑病)的
作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理1周龄的小麦植株cv.Arina。施用1天后,通过向试验植株喷洒孢子悬浮液(5×105分生孢子/ml)来接种小麦植株。在20℃和95%相对湿度下保温培养1天后,在20℃和60%相对湿度的温室中,将植株保持10天。接种后11天,评定病害发生率。
使用每种化合物1.01、1.03、1.08和1.10,实际上彻底预防了侵染(0-5%侵染)。
实施例B-8:对大麦上的圆长蠕孢(大麦网斑病)的作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理1周龄的大麦植株cv.Regina。施用2天后,通过向试验植株喷洒孢子悬浮液(3×104分生孢子/ml)来接种大麦植株。在20℃和95%相对湿度的温室中保温培养4天后,评定病害发生率。
使用每种化合物1.01、1.03、1.08、1.10、1.12、1.13、1.15、1.16、1.18、1.19、1.22、1.24、1.33、1.36、1.35、1.56、1.57、1.60、1.66、1.67、1.69、1.70、1.77、1.78、1.81、1.106、1.107、1.138、1.139、1.151、1.152、1.154、1.155、1.182、1.185、1.251、1.252、2.01、2.08、2.66、3.01、3.08、3.12、3.18、3.32、3.35、3.56、3.66、3.69、9.01、9.06、9.15、9.21、9.41、9.50、9.53、9.59、9.62、15.25、15.26和15.28,实际上彻底预防了侵染(0-5%侵染)。
实施例B-9:对番茄上的马铃薯早疫病链格孢(番茄早疫病)的
作用
喷雾室中,用配制的试验化合物(0.02%活性成分)处理4周龄的番茄植株cv.Roter Gnom。施用2天后,通过向试验植株上喷洒孢子悬浮液(2×105分生孢子/ml)来接种番茄植株。在20℃和95%相对湿度的生长室中保温培养3天后,评定病害发生率。
使用每种化合物1.01、1.03、1.08、1.10、1.13、1.15、1.16、1.19、1.22、1.24、1.33、1.35、1.36、1.56、1.57、1.67、1.69、1.70、1.77、1.78、1.81、1.107、1.151、1.152、1.154、1.155、1.182、1.185、1.251、1.252、2.01、3.01、3.08、3.12、3.32、3.35、3.56、3.69、9.01、9.06、9.15、9.41、9.50、9.62和15.26,实际上彻底预防了侵染(0-5%侵染)。
实施例B-10:对葡萄上的葡萄白粉病钩丝壳霉(葡萄白粉病)的
作用
在喷雾室中,用配制的试验化合物(0.02%活性成分)处理5周龄的葡萄秧苗cv.Gutedel。施用1天后,通过在试验植株的上方摇动感染了葡萄白粉病的植株来接种葡萄植株。在26℃和60%相对湿度、14/10小时(亮/暗)的光照方案下保温培养7天后,评定病害发生率。
使用每种化合物1.01、1.03、1.08、1.10、1.12、1.13、1.18、1.19、1.24、1.33、1.56、1.57、1.60、1.66、1.67、1.70、1.77、1.78、1.81、1.106、1.107、1.138、1.139、1.151、1.152、1.154、1.155、1.182、1.185、1.251、1.252、2.01、2.08、2.66、3.01、3.08、3.12、3.32、3.56、3.66、3.69、3.250、9.01、9.06、9.15、9.41、9.50、9.53和9.59,实际上彻底预防了侵染(0-5%侵染)。
实施例B-11:对小麦上的小麦壳针孢(小麦叶枯病)的作用
在喷雾室中,用配制的试验化合物(0.2%活性成分)处理2周龄的小麦植株cv.Riband。施用1天后,通过向试验植株喷洒孢子悬浮液(10×105分生孢子/ml)来接种小麦植株。在23℃和95%相对湿度下保温培养1天后,在23℃和60%相对湿度下,将植株在温室中保持16天。接种后18天,评定病害发生率。
在该试验中,化合物1.10、1.03、1.09、1.70、1.69、3.01、1.67、1.66、3.66、9.59、3.69、1.33、2.66、9.06、3.08、1.77、1.78、1.56、1.57、1.138、1.139、1.12、1.18、1.106、1.107、9.53、3.32、1.151、1.152、1.252、1.155、9.41、3.56、1.13、3.12、9.21、1.250、1.19和3.18都表现出良好的活性(<20%病害发生率)。
Claims (12)
1.式(I)化合物:
其中Het是含有1-3个杂原子的5-或6-元杂环,每个杂原子独立地选自氧、氮和硫,条件是:该环不是1,2,3-三唑,该环被1个、2个或3个Ry基团取代;R1是氢、甲酰基、CO-C1-4烷基、COO-C1-4烷基、C1-4烷氧基(C1-4)亚烷基、CO-C1-4亚烷氧基(C1-4)烷基、炔丙基或丙二烯基;R2、R3、R4和R5各自独立地为氢、卤素、甲基或CF3;每个R6独立地为卤素、甲基或CF3;R7是(Z)mC≡C(Y1)、(Z)mC(Y1)=C(Y2)(Y3)或三(C1-4)烷基甲硅烷基;每个Ry独立地为卤素、C1-3烷基、C1-3卤代烷基、C1-3烷氧基(C1-3)亚烷基或氰基;X是O或S;Y1、Y2和Y3各自独立地为氢、卤素、C1-6烷基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素、羟基、C1-4烷氧基、C1-4卤代烷氧基、C1-4烷硫基、C1-4卤代烷硫基、C1-4烷基氨基、二(C1-4)烷基氨基、C1-4烷氧基羰基、C1-4烷基羰基氧和三(C1-4)烷基甲硅烷基]、C2-4链烯基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素]、C2-4炔基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素]、C3-7环烷基[任选地被一个或多个取代基取代,每个取代基独立地选自卤素、C1-4烷基和C1-4卤代烷基]或三(C1-4)烷基甲硅烷基;Z是C1-4亚烷基[任选地被一个或多个取代基取代,每个取代基独立地选自羟基、氰基、C1-4烷氧基、卤素、C1-4卤代烷基、C1-4卤代烷氧基、C1-4烷硫基、COOH和COO-C1-4烷基];m是0或1;且n是0、1或2。
2.如权利要求1所述的式(I)化合物,其中Het是吡唑、吡咯、噻吩、呋喃、噻唑、异噻唑、噁唑、异噁唑、吡啶、吡嗪、嘧啶、哒嗪、5,6-二氢吡喃或5,6-二氢-1,4-氧硫杂环己二烯。
3.如权利要求1或2所述的式(I)化合物,其中R1是氢、炔丙基、丙二烯基、甲酰基、COMe、COEt或COCH2OMe。
4.如权利要求1、2或3所述的式(I)化合物,其中Y1、Y2和Y3独立地是氢、卤素、C1-6烷基、C1-3卤代烷基、C1-4(卤代烷氧基)C1-4烷基、C1-4(卤代烷硫基)C1-4烷基、三甲基甲硅烷基、C2-4链烯基、C2-4卤代链烯基或C3-6环烷基(任选地被一个或多个取代基取代,每个取代基独立地选自卤素和C1-2烷基)。
5.如权利要求1、2、3或4所述的式(I)化合物,其中m=0。
6.如权利要求1、2、3、4或5所述的式(I)化合物,其中Z是C1-2亚烷基[其可以任选地被一个或多个取代基取代,每个取代基独立地选自卤素、C1-4卤代烷基和C1-4卤代烷氧基]。
7.如权利要求1、2、3、4、5或6所述的式(I)化合物,其中R7是在4’位。
8.如权利要求1、2、3、4、5、6或7所述的式(I)化合物,其中n=0。
10.式(III)化合物:
其中R2、R3、R4、R5、R6、R7和n是如权利要求1中所定义的,且Hal是溴、氯或碘;条件是:该化合物不是根据表0的式(IIIa)化合物。
11.用于控制微生物和预防微生物对植物的侵袭和侵染的组合物,其中活性成分是与合适的载体在一起的如权利要求1所述的式(I)化合物。
12.控制或预防致植物病微生物对栽培的植物的侵染的方法,其包括向植物、其部分或其所在地施用如权利要求1所述的式(I)化合物。
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CN103348989A (zh) * | 2013-07-15 | 2013-10-16 | 江苏龙灯化学有限公司 | 一种杀真菌混合物 |
CN103947644A (zh) * | 2005-08-05 | 2014-07-30 | 巴斯夫欧洲公司 | 包含取代的1-甲基吡唑-4-基甲酰苯胺的杀真菌混合物 |
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DE102005060464A1 (de) * | 2005-12-17 | 2007-06-28 | Bayer Cropscience Ag | Pyrazolylcarboxamide |
TWI372752B (en) * | 2005-12-22 | 2012-09-21 | Nihon Nohyaku Co Ltd | Pyrazinecarboxamide derivatives and plant disease controlling agents containing the same |
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UY30090A1 (es) | 2006-01-16 | 2007-08-31 | Syngenta Participations Ag | Insecticidas novedosos |
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EP2003974A1 (en) * | 2006-04-06 | 2008-12-24 | Syngeta Participations AG | Fungicidal compositions |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103947644A (zh) * | 2005-08-05 | 2014-07-30 | 巴斯夫欧洲公司 | 包含取代的1-甲基吡唑-4-基甲酰苯胺的杀真菌混合物 |
CN103348989A (zh) * | 2013-07-15 | 2013-10-16 | 江苏龙灯化学有限公司 | 一种杀真菌混合物 |
CN103348989B (zh) * | 2013-07-15 | 2015-08-12 | 江苏龙灯化学有限公司 | 一种杀真菌混合物 |
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