CN107426999A - 具有杀真菌活性的吡啶酰胺化合物 - Google Patents
具有杀真菌活性的吡啶酰胺化合物 Download PDFInfo
- Publication number
- CN107426999A CN107426999A CN201580072891.4A CN201580072891A CN107426999A CN 107426999 A CN107426999 A CN 107426999A CN 201580072891 A CN201580072891 A CN 201580072891A CN 107426999 A CN107426999 A CN 107426999A
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- Prior art keywords
- compound
- saturated hydrocarbon
- aliphatic saturated
- hydrocarbon base
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 Picolinamide compound Chemical class 0.000 title description 102
- 150000001875 compounds Chemical class 0.000 claims description 294
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 81
- 125000001931 aliphatic group Chemical group 0.000 claims description 78
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 40
- 239000000417 fungicide Substances 0.000 abstract description 36
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 abstract description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 454
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 210
- 239000000203 mixture Substances 0.000 description 160
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 153
- 239000002585 base Substances 0.000 description 111
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 102
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 100
- 239000000243 solution Substances 0.000 description 91
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 85
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 241000196324 Embryophyta Species 0.000 description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- 238000005160 1H NMR spectroscopy Methods 0.000 description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 239000000376 reactant Substances 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- 150000002148 esters Chemical class 0.000 description 51
- 235000019441 ethanol Nutrition 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 46
- 229910052681 coesite Inorganic materials 0.000 description 46
- 229910052906 cristobalite Inorganic materials 0.000 description 46
- 238000002360 preparation method Methods 0.000 description 46
- 239000000377 silicon dioxide Substances 0.000 description 46
- 229910052682 stishovite Inorganic materials 0.000 description 46
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- 150000002924 oxiranes Chemical class 0.000 description 45
- 238000003818 flash chromatography Methods 0.000 description 42
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 40
- 238000012545 processing Methods 0.000 description 40
- 239000012230 colorless oil Substances 0.000 description 38
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- 241000894006 Bacteria Species 0.000 description 35
- 244000025254 Cannabis sativa Species 0.000 description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
- 150000001412 amines Chemical class 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 30
- 239000004519 grease Substances 0.000 description 30
- 239000012074 organic phase Substances 0.000 description 30
- 239000011734 sodium Substances 0.000 description 30
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- 239000007864 aqueous solution Substances 0.000 description 29
- 238000005191 phase separation Methods 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- 201000010099 disease Diseases 0.000 description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
- 238000000034 method Methods 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
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- 238000001914 filtration Methods 0.000 description 26
- 229910052731 fluorine Inorganic materials 0.000 description 26
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- 241000209140 Triticum Species 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 23
- 239000011737 fluorine Substances 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- 239000007788 liquid Substances 0.000 description 22
- 235000021307 Triticum Nutrition 0.000 description 21
- 235000019260 propionic acid Nutrition 0.000 description 20
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 19
- 239000007832 Na2SO4 Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- 238000010792 warming Methods 0.000 description 18
- 239000005864 Sulphur Substances 0.000 description 17
- 239000010408 film Substances 0.000 description 17
- 229910052698 phosphorus Inorganic materials 0.000 description 17
- 239000011574 phosphorus Substances 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 239000012141 concentrate Substances 0.000 description 15
- 239000003513 alkali Substances 0.000 description 14
- 150000003851 azoles Chemical class 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 238000005406 washing Methods 0.000 description 14
- 241000726221 Gemma Species 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 241000221785 Erysiphales Species 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 10
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241000233866 Fungi Species 0.000 description 9
- 240000005979 Hordeum vulgare Species 0.000 description 9
- 235000007340 Hordeum vulgare Nutrition 0.000 description 9
- 239000012448 Lithium borohydride Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 150000001336 alkenes Chemical group 0.000 description 9
- 239000003139 biocide Substances 0.000 description 9
- 238000011081 inoculation Methods 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 241000222235 Colletotrichum orbiculare Species 0.000 description 8
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 229910000085 borane Inorganic materials 0.000 description 8
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- 229910052757 nitrogen Inorganic materials 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
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- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
- QVHJQCGUWFKTSE-YFKPBYRVSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)OC(C)(C)C QVHJQCGUWFKTSE-YFKPBYRVSA-N 0.000 description 7
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 241000540505 Puccinia dispersa f. sp. tritici Species 0.000 description 7
- 230000003115 biocidal effect Effects 0.000 description 7
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 7
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- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 7
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
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- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 6
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Abstract
本发明涉及式I的吡啶酰胺以及它们作为杀真菌剂的用途。
Description
相关申请的交叉引用
本申请要求在2014年12月30日提交的美国临时专利申请序列号62/098089、在2014年12月30日提交的美国临时专利申请序列号62/098097、在2015年11月13日提交的美国临时专利申请序列号62/255144、在2015年11月13日提交的美国临时专利申请序列号62/255152、在2015年11月13日提交的美国临时专利申请序列号62/255163、在2015年11月13日提交的美国临时专利申请序列号62/255168、在2015年11月13日提交的美国临时专利申请序列号62/255125和在2015年11月13日提交的美国临时专利申请序列号62/255131的权益,其明确通过参考并入本申请。
背景技术和发明内容
本申请涉及吡啶酰胺以及它们作为杀真菌剂的用途。本申请的化合物可以提供对抗子囊菌(ascomycetes),担子菌(basidiomycetes),半知菌(deuteromycetes),和卵菌(oomycetes)的保护。
本申请的一种实施方式可以包括式I的化合物:
其中
X是H或C(O)R5;
Y是H,C(O)R5,或Q;
Q是
R1和R11独立地选自氢或脂族饱和烃基,其任选取代有0个、1个或多个R8;或者,R1和R11可以共同形成3-6元饱和或部分饱和的碳环或杂环,其任选取代有0个、1个或多个R8;
R2和R12独立地选自氢,脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8;
R3选自氢,C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8;
R4选自脂族饱和烃基,芳基,或酰基,它们各自任选取代有0个、1个或多个R8;
R5选自脂族饱和烃基氧基或苄氧基,它们各自任选取代有0个、1个或多个R8;
R6选自氢,脂族饱和烃基氧基,或卤素,它们各自任选取代有0个、1个或多个R8;
R7选自氢,-C(O)R9,或-CH2OC(O)R9;
R8选自氢,脂族饱和烃基,芳基,酰基,卤素,烯基,脂族饱和烃基氧基,或杂环基,它们各自任选取代有0个、1个或多个R10;
R9选自脂族饱和烃基,脂族饱和烃基氧基,或芳基,它们各自任选取代有0个、1个或多个R8;
R10选自氢,脂族饱和烃基,芳基,酰基,卤素,烯基,脂族饱和烃基氧基,或杂环基。
本申请另一种实施方式可包括用于防治或预防真菌侵袭的杀真菌组合物,所述组合物包含如上所述的化合物和植物学可接受的载体物质。
本申请另一种实施方式可包括用于防治或预防真菌侵袭植物的方法,所述方法包括以下步骤,将杀真菌有效量的如上所述的一种或多种化合物施用至真菌、植物、和与所述植物邻近的区域中的至少一个中。
本领域技术人员应该理解的是,以下术语可以包括它们定义内的一般性″R″-基团,例如,″术语脂族饱和烃基氧基是指-OR取代基″。也应该理解的是,在以下术语的定义内,针对说明的目的而包括这些″R″基团,但不应理解为其限制关于式I的取代或受式I的取代的限制。
术语“脂族饱和烃基(alkyl)”是指支化的、非支化的、或饱和环状的碳链,包括但不限于甲基,乙基,丙基,丁基,异丙基,异丁基,叔丁基,戊基,己基,环丙基,环丁基,环戊基,环己基等。
术语“烯基”是指包含一个或多个双键的支化的、非支化的、或环状的碳链,包括但不限于乙烯基,丙烯基,丁烯基,异丙烯基,异丁烯基,环丁烯基,环戊烯基,环己烯基等。
术语“炔基”是指包含一个或多个三键的支化或非支化的碳链,包括但不限于丙炔基,丁炔基等。
术语“芳基”和“Ar”是指包含0个杂原子的任何芳环,单环或双环。
术语“杂环基”是指包含一个或多个杂原子的任何芳族或非芳族的环、单环或双环。
术语“脂族饱和烃基氧基”是指-OR取代基。
术语“酰氧基”是指-OC(O)R取代基。
术语“氰基”是指-C≡N取代基。
术语“羟基”是指-OH取代基。
术语“氨基”是指-N(R)2取代基。
术语“芳基脂族饱和烃基氧基”是指-O(CH2)nAr,其中n是选自1、2、3、4、5、或6的整数。
术语“卤代脂族饱和烃基氧基”是指-OR-X取代基,其中X是Cl,F,Br,或I,或其任何组合。
术语“卤代脂族饱和烃基”是指取代有Cl、F、I、或Br或其任何组合的脂族饱和烃基。
术语“卤素”或“卤代”是指一个或多个卤素原子,限定为F,Cl,Br,和I。
术语“硝基”是指-NO2取代基。
术语脂族饱和烃基硫基是指-SR取代基。
在本申请全文中,当提到式I化合物时还包括所有立体异构体,例如非对映异构体、对映异构体、及其混合物。在另一种实施方式中,提到的式(I)也包括其盐或水合物。示例性的盐包括但不限于:氢氯酸盐、氢溴酸盐、氢碘酸盐、三氟乙酸盐、和三氟甲磺酸盐。
本领域技术人员还应当理解的是,除非另有说明,允许额外的取代,只要满足化学键合和应变能规则并且产物仍表现杀真菌活性。
本申请另一实施方式为式I化合物的用途,用于保护植物免受致植物病微生物侵袭或用于处理被致植物病微生物侵害的植物,所述用途包括将式I化合物或含有所述化合物的组合物施用至土壤、植物、植物的一部分、叶子和/或根。
此外,本申请的另一种实施方式为用于保护植物免受致植物病微生物侵袭和/或处理被致植物病微生物侵害的植物的组合物,所述组合物包含式I化合物和植物学可接受的载体物质。
具体实施方式
可通过各种已知技术中的任一种将本申请化合物作为化合物或作为含有所述化合物的制剂来施用。例如,可将所述化合物施用至植物的根或叶子以防治各种真菌,而不破坏植物的商业价值。所述物质可按通常使用的任意制剂类型的形式施用,例如作为溶液剂、粉剂、可润湿粉末、可流动浓缩物、或乳油(emulsifiable concentrate)。
优选地,本申请化合物以制剂形式施用,所述制剂包含一种或多种式I化合物和植物学可接受的载体。可将浓缩制剂分散在水中或其它液体中用于施用,或制剂可以是粉尘或颗粒,其不经进一步处理随即可施用。可根据农业化学领域常见的方法制备所述制剂。
本申请预期使用所有媒介物,可通过所述媒介物配制所述一种或多种化合物用于递送并用作杀真菌剂。通常,作为含水悬浮液或乳液的形式施用制剂。所述悬浮液或乳液可由水可溶、水可悬浮或可乳化制剂制备,当所述水可溶、水可悬浮或可乳化制剂为固体时通常称作可润湿粉末;或者当所述水可溶、水可悬浮或可乳化制剂为液体时通常称作乳油、含水悬浮液或悬浮浓缩物。容易理解的是,可使用能将这些化合物加入其中的任意物质,条件是得到所需的用途而不明显妨碍这些化合物作为抗真菌剂的活性。
可被压制成水可分散颗粒的可润湿粉末包含一种或多种式I化合物、惰性载体和表面活性剂的匀质混合物(intimate mixture)。以可润湿粉末的总重量计,所述可润湿粉末中的化合物的浓度可从约10wt%至约90wt%,更优选从约25wt%至约75wt%。在可润湿粉末制剂的制备中,所述化合物可与任意微细粉碎的固体混合,所述微细粉碎的固体为例如叶蜡石(prophyllite)、滑石、白垩、石膏、漂白土(Fuller′s earth)、膨润土、凹凸棒石、淀粉、酪蛋白(casein)、麸质(gluten)、蒙脱土(montmorillonite clay)、硅藻土(diatomaceous earth)、精制硅酸盐(purified silicate)等。在所述操作中,通常将微细粉碎的载体和表面活性剂与所述化合物共混并研磨。
以所述乳油的总重量计,式I化合物的乳油可以包含于合适液体中的常规浓度的所述化合物,例如从约1wt%至约50wt%。可将所述化合物溶解在惰性载体中,所述惰性载体是水混溶性溶剂或水不混溶性有机溶剂和乳化剂的混合物。所述乳油可用水和油稀释以形成水包油乳液形式的喷雾混合物。有用的有机溶剂包括石油的芳族部分特别是高沸点环烷部分和烯部分例如重芳香族石脑油。也可使用其它有机溶剂例如萜烯溶剂包括松香衍生物、脂肪族酮例如环己酮和复杂的醇(complex alchol)例如2-乙氧基乙醇。
可被本申请有利地采用的乳化剂可容易地由本领域技术人员确定并包括各种非离子乳化剂、阴离子乳化剂、阳离子乳化剂和两性乳化剂,或两种或多种乳化剂的共混物。用在制备所述乳油中的非离子乳化剂的实例包括聚亚烷基二醇醚,和脂族饱和烃基和芳基酚、脂肪族醇、脂肪族胺或脂肪酸与环氧乙烷、环氧丙烷的缩合产物,例如乙氧基化脂族饱和烃基酚和用多元醇或聚氧化烯溶解的羧酸酯。阳离子乳化剂包括季铵化合物和脂肪胺盐。阴离子乳化剂包括脂族饱和烃基芳基磺酸的油溶盐(例如,钙盐)、油溶盐或硫酸化聚二醇醚和磷酸化聚二醇醚的合适盐。
本申请化合物的乳油的制备中可采用的代表性有机液体为芳族液体例如二甲苯和丙基苯馏分;或混合的萘馏分、矿物油、取代的芳族有机液体例如邻苯二甲酸二辛酯;煤油(kerosene);各种脂肪酸的二脂族饱和烃基酰胺,特别是脂肪二醇的二甲基酰胺和二醇衍生物例如二甘醇的正丁基醚、乙基醚或甲基醚,三甘醇的甲基醚,石油馏分或烃例如矿物油,芳族溶剂,石蜡油等;植物油,例如大豆油,油菜籽油,橄榄油,蓖麻油,向日葵种子油,椰子油,玉米油,棉籽油,亚麻子油,棕榈油,花生油,红花油,芝麻油,桐油等;以上植物油的酯;和类似物。在乳油的制备中也可采用两种或多种有机液体的混合物。有机液体包括二甲苯和丙基苯馏分,在一些情况下二甲苯是最优选的。在液体制剂中通常采用表面活性分散剂,并且以所述分散剂和一种或多种化合物的组合重量计,所述表面活性分散剂的量为0.1至20wt%。所述制剂也可含有其它相容的添加剂,例如植物生长调节剂和其它农业中使用的生物活性化合物。
含水悬浮液包括一种或多种水不可溶式I化合物分散在含水媒介物中的悬浮液,以含水悬浮液的总重量计,浓度为约1wt%-约50wt%。如下制备悬浮液:精细研磨一种或多种所述化合物,将经研磨的化合物剧烈混合到媒介物中,所述媒介物由水和选自上述相同类型的表面活性剂构成。也可加入其它成分,例如无机盐以及合成胶或天然胶,以增加含水媒介物的密度和粘度。
式I化合物也可作为颗粒制剂的形式施用,所述颗粒制剂可特别用于施用至土壤。以颗粒制剂的总重量计,所述颗粒制剂通常含有分散在惰性载体中的约0.5wt%-约10wt%所述化合物,所述惰性载体完全或大部分由粗糙粉碎的惰性物质组成,所述惰性物质为例如凹凸棒石、膨润土、硅藻土、粘土或相似的廉价物质。所述制剂通常如下制备:将所述化合物溶解在合适的溶剂中,将其施用至颗粒载体,所述颗粒载体已经被预先制成合适的粒度(范围为约0.5至3mm)。合适的溶剂为所述化合物可基本或完全溶于其中的溶剂。所述制剂也可如下制备:将所述载体和化合物和溶剂制成糊状或膏状,然后压碎并干燥得到所需颗粒粒度。
含有式I化合物的粉剂(dust)可以如下制备:匀质混合粉末状的一种或多种所述化合物和合适的粉尘状农用载体(例如高岭粘土、研碎的火山石等)。以粉剂的总重量计,所述粉剂可合适地含有约1%-约10%所述化合物。
所述制剂可额外含有辅助表面活性剂以增强所述化合物沉积、润湿和渗透到目标作物和微生物上。这些辅助表面活性剂可任选作为制剂的组分或作为罐混合物使用。以水的喷雾体积计,所述辅助表面活性剂的量通常从0.01至1.0体积%,优选0.05至0.5体积%。合适的辅助表面活性剂包括但不限于乙氧基化壬基酚、乙氧基化合成醇或乙氧基化天然醇、磺基琥珀酸酯或磺基琥珀酸盐、乙氧基化有机硅、乙氧基化脂肪胺,表面活性剂与矿物油或植物油的共混物,作物油浓缩物(矿物油(85%)+乳化剂(15%));壬基酚乙氧基化物;苄基椰油脂族饱和烃基二甲基季铵盐;石油烃、脂族饱和烃基酯、有机酸、和阴离子表面活性剂的共混物;C9-C11脂族饱和烃基聚糖苷;磷酸化的醇乙氧基化物;天然伯醇(C12-C16)乙氧基化物;二-仲-丁基苯酚EO-PO嵌段共聚物;聚硅氧烷-甲基封端物;壬基酚乙氧基化物+脲硝酸铵;乳化的甲基化的种子油;十三脂族饱和烃基醇(合成)乙氧基化物(8EO);牛油胺乙氧基化物(15 EO)和PEG(400)二油酸酯-99。所述制剂也可包括水包油乳液例如在美国专利申请11/495,228中披露的那些,将美国专利申请11/495,228披露的内容并入本文作为参考。
所述制剂可任选包括含有其它杀生物化合物的组合。所述额外的杀生物化合物可以是杀真菌剂、杀昆虫剂、除草剂、杀线虫剂、杀螨剂、杀节肢动物剂(arthropodicide)、杀细菌剂或它们的组合,所述额外的杀生物化合物在就应用所选的介质中与本申请化合物相容并且不拮抗本申请化合物的活性。因此,在所述实施方式中,将所述其它杀生物化合物作为增补毒剂使用,用于相同或不同的杀生物用途。所述组合中的所述式I化合物和杀生物化合物通常可以1∶100至100∶1的重量比存在。
本申请化合物也可与其它杀真菌剂组合形成杀真菌混合物和它们的协同混合物。本申请的杀真菌化合物通常与一种或多种其它杀真菌剂联合施用,从而防治更宽范围的不期望病害。当与其它杀真菌剂联合施用时,本申请要求保护的化合物可与一种或多种其它杀真菌剂配制在一起,可与一种或多种其它杀真菌剂桶混(tank mix)在一起,或可与一种或多种其它杀真菌剂顺序施用。所述其它杀真菌剂可包括2-(氰硫基甲硫基)-苯并噻唑(2-(thiocyanatomethylthio)-benzothiazole),2-苯基-苯酚(2-phenylphenol),8-羟基喹啉硫酸盐(8-hydroxyquinoline sulfate),辛唑嘧菌胺(ametoctradin),吲唑磺菌胺(amisulbrom),抗霉素(antimycin),白粉寄生孢(Ampelomyces quisqualis),阿扎康唑(azaconazole),腈嘧菌酯(azoxystrobin),芽孢杆菌(Bacillus subtilis),芽孢杆菌菌株QST713(Bacillus subtilis strain QST713),苯霜灵(benalaxyl),苯菌灵(benomyl),苯噻菌胺酯(benthiavalicarb-iso丙基),苯并烯氟菌唑(benzovindiflupyr),苄基氨基苯-磺酸(BABS)盐(benzylaminobenzene-sulfonate(BABS)salt),碳酸氢盐(bicarbonates),联苯类化合物(biphenyl),叶枯唑(bismerthiazol),联苯三唑醇(bitertanol),bixafen,灭瘟素(blasticidin-S),硼砂(borax),波尔多液(Burgundy mixture),烟酰胺(boscalid),糠菌唑(bromuconazole),乙嘧酚磺酸酯(bupirimate),石硫合剂(calciumpolysulfide),敌菌丹(captafol),克菌丹(captan),多菌灵(carbendazim),萎锈灵(carboxin),环丙酰菌胺(carpropamid),香芹酮(carvone),氯芬同(chlazafenone),地茂散(chloroneb),百菌清(chlorothalonil)、乙菌利(chlozolinate),盾壳霉(ConiothyriumMinitans),氢氧化铜(copper hydroxide),辛酸酮(copper octanoate),王铜(copperoxychloride),硫酸铜(copper sulfate),碱式硫酸铜(copper sulfate(tribasic)),氧化亚铜(cuprous oxide),氰霜唑(cyazofamid),环氟苄酰胺(cyflufenamid),霜脲氰(cymoxanil),环菌唑(cyproconazole),嘧菌环胺(cyprodinil),棉隆(dazomet),咪菌威(debacarb),亚乙基二-(二硫代氨基甲酸)二铵(diammonium ethylenebis-(dithiocarbamate)),苯氟磺胺(dichlofluanid),双氯酚(dichlorophen),双氯氰菌胺(diclocymet),哒菌酮(diclomezine),氯硝胺(dichloran),乙霉威(diethofencarb),苯醚甲环唑(difenoconazole),野燕枯离子(difenzoquat ion),氟嘧菌胺(diflumetorim),烯酰吗啉(dimethomorph),醚菌胺(dimoxystrobin),烯唑醇(diniconazole),精烯唑醇(diniconazole-M),消螨通(dinobuton),二硝巴豆酸酯(dinocap),二苯基胺(diphenylamine),二氰蒽醌(dithianon),十二环吗啉(dodemorph),十二环吗啉乙酸盐(dodemorph acetate),多果定(dodine),多果定游离碱(dodine free base),敌瘟磷(edifenphos),enestrobin,烯肟菌酯(enestroburin),氟环唑(epoxiconazole),噻唑菌胺(ethaboxam),乙氧喹啉(ethoxyquin),土菌灵(etridiazole),噁唑菌酮(famoxadone),咪唑菌酮(fenamidone),氯苯嘧啶醇(fenarimol),腈苯唑(fenbuconazole),甲呋酰胺(fenfuram),环酰菌胺(fenhexamid),稻瘟酰胺(fenoxanil),拌种咯(fenpiclonil),苯锈啶(fenpropidin),丁苯吗啉(fenpropimorph),fenpyrazamine,三苯锡(fentin),三苯基乙酸锡(fentin acetate),三苯基氢氧化锡(fentin hydroxide),福美铁(ferbam),嘧菌腙(ferimzone),氟啶胺(fluazinam),咯菌腈(fludioxonil),氟吗啉(flumorph),氟吡菌胺(fluopicolide),氟吡菌酰胺(fluopyram),氟氯菌核利(fluoroimide),氟嘧菌酯(fluoxastrobin),氟喹唑(fluquinconazole),氟硅唑(flusilazole),磺菌胺(flusulfamide),氟噻菌净(flutianil),氟酰胺(flutolanil),粉唑醇(flutriafol),fluxapyroxad,灭菌丹(folpet),甲醛(formaldehyde),三乙膦酸(fosetyl),三乙膦酸铝(fosetyl-aluminium),麦穗宁(fuberidazole),呋霜灵(furalaxyl),呋吡菌胺(furametpyr),双胍辛(guazatine),双胍辛乙酸盐(guazatine acetates),四硫钠(GY-81),六氯苯(hexachlorobenzene),己唑醇(hexaconazole),噁霉灵(hymexazol),抑霉唑(imazalil),硫酸抑霉唑(imazalil sulfate),亚胺唑(imibenconazole),双胍辛胺(iminoctadine),三乙酸双胍辛胺(iminoctadine triacetate),双胍辛胺三(对十二脂族饱和烃基苯磺酸盐)[iminoctadine tris(albesilate)],iodocarb,种菌唑(ipconazole),ipfenpyrazolone,异稻瘟净(iprobenfos),异菌脲(iprodione),缬霉威(iprovalicarb),稻瘟灵(isoprothiolane),吡唑萘菌胺(isopyrazam),异噻菌胺(isotianil),春雷霉素(kasugamycin),春雷霉素盐酸盐水合物(kasugamycin hydrochloride hydrate),醚菌甲酯(kresoxim-methyl),laminarin,代森锰铜(mancopper),代森锰锌(mancozeb),双炔酰菌胺(mandipropamid),代森锰(maneb),精甲霜灵(mefenoxam),嘧菌胺(mepanipyrim),灭锈胺(mepronil),二硝巴豆酸酯(meptyl-dinocap),氯化汞(mercuric chloride),氧化汞(mercuric oxide),氯化亚汞(mercurous chloride),甲霜灵(metalaxyl),精甲霜灵(metalaxyl-M),威百亩(metam),安百亩(metam-ammonium),metam-potassium,威百亩(metam-sodium),叶菌唑(metconazole),磺菌威(methasulfocarb),碘甲烷(methyliodide),异硫氰酸甲酯(methyl isothiocyanate),代森联(metiram),苯氧菌胺(metominostrobin),苯菌酮(metrafenone),米多霉素(mildiomycin),腈菌唑(myclobutanil),代森钠(nabam),酞菌异丙酯(nitrothal-iso丙基),氟苯嘧啶醇(nuarimol),辛噻酮(octhilinone),呋酰胺(ofurace),油酸(脂肪酸)(oleic acid(fattyacid)),肟醚菌胺(orysastrobin),噁霜灵(oxadixyl),喹啉铜(oxine-copper),富马酸噁咪唑(oxpoconazole fumarate),氧化萎锈灵(oxycarboxin),稻瘟酯(pefurazoate),戊菌唑(penconazole),戊菌隆(pencycuron),戊苯吡菌胺(penflufen),五氯酚(pentachlorophenol),月桂酸五氯苯酯(pentachlorophenyl laurate),吡噻菌胺(penthiopyrad),乙酸苯汞(phenylmercury acetate),膦酸(phosphonic acid),四氯苯酞(phthalide),啶氧菌酯(picoxystrobin),多抗霉素B(polyoxin B),多抗霉素(polyoxins),多氧霉素(polyoxorim),碳酸氢钾(potassium bicarbonate),羟基喹啉硫酸钾(potassium hydroquinoline sulfate),烯丙苯噻唑(probenazole),咪鲜胺(prochloraz),腐霉利(procymidone),霜霉威(propamocarb),盐酸霜霉威(propamocarbhydrochloride),丙环唑(propiconazole),丙森锌(propineb),丙氧喹啉(proquinazid),丙硫菌唑(prothioconazole),吡唑醚菌酯(pyraclostrobin),唑胺菌酯(pyrametostrobin),唑菌酯(pyraoxystrobin),吡菌磷(pyrazophos),pyribencarb,稗草丹(pyributicarb),啶斑肟(pyrifenox),嘧霉胺(pyrimethanil),pyriofenone,咯喹酮(pyroquilon),灭藻醌(quinoclamine),苯氧喹啉(quinoxyfen),五氯硝基苯(quintozene),大虎杖提取物(Reynoutria sachalinensis extract),环丙吡菌胺(sedaxane),硅噻菌胺(silthiofam),硅氟唑(simeconazole),2-苯基苯酚钠(sodium 2-phenyl phenoxide),碳酸氢钠(sodium bicarbonate),五氯苯酚钠(sodiumpentachlorophenoxide),螺环菌胺(spiroxamine),硫黄(sulfur),SYP-Z048,木焦油(taroil),戊唑醇(tebuconazole),异丁乙氧喹啉(tebufloquin),四氯硝基苯(tecnazene),四氟醚唑(tetraconazole),噻菌灵(thiabendazole),噻氟菌胺(thifluzamide),甲基硫菌灵(thiophanate-methyl),福美双(thiram),噻酰菌胺(tiadinil),甲基立枯磷(tolclofos-methyl),甲苯氟磺胺(tolylfluanid),三唑酮(triadimefon),三唑醇(triadimenol),咪唑嗪(triazoxide),三环唑(tricyclazole),十三吗啉(tridemorph),肟菌酯(trifloxystrobin),氟菌唑(triflumizole),嗪氨灵(triforine),灭菌唑(triticonazole),井冈霉素(validamycin),valifenalate,valiphenal,乙烯菌核利(vinclozolin),代森锌(zineb),福美锌(ziram),苯酰菌胺(zoxamide),假丝酵母(Candidaoleophila),枯萎病菌(Fusarium oxysporum),绿粘帚霉属种(Gliocladium spp.),大隔孢拟射脉霉素(Phlebiopsis gigantea),灰绿链霉菌(Streptomyces griseoviridis),木霉属种(Trichoderma spp.),(RS)-N-(3,5-二氯苯基)-2-(甲氧基甲基)-琥珀酰亚胺((RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide),1,2-二氯丙烷(1,2-dichloropropane),1,3-二氯-1,1,3,3-四氟丙酮水合物(1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate),1-氯-2,4-二硝基萘(1-chloro-2,4-dinitronaphthalene),1-氯-2-硝基丙烷(1-chloro-2-nitropropane),2-(2-十七脂族饱和烃基-2-咪唑啉-1-基)乙醇(2-(2-heptadecyl-2-imidazolin-1-yl)ethanol),2,3-二氢-5-苯基-1,4-二硫杂环己二烯-1,1,4,4-四氧化物(2,3-二氢-5-phenyl-1,4-dithi-ine1,1,4,4-tetraoxide),乙酸2-甲氧基乙基汞(2-methoxyethylmercury acetate),氯化2-甲氧基乙基汞(2-methoxyethylmercury chloride),硅酸2-甲氧基乙基汞(2-methoxyethylmercury silicate),3-(4-氯苯基)-5-甲基绕丹宁(3-(4-chlorophenyl)-5-methyl rhodanine),硫氰酸4-(2-硝基丙-1-烯基)苯酯(4-(2-nitroprop-l-enyl)phenylthiocyanateme),氨丙膦酸(am丙基fos),敌菌灵(anilazine),氧化福美双(azithiram),多硫化钡(barium polysulfide),铁菌清(Bayer 32394),麦锈灵(benodanil),醌肟腙(benquinox),丙唑草隆(bentaluron),苄烯酸(benzamacril);苄烯酸异丁酯(benzamacril-isobutyl),苯杂吗(benzamorf),乐杀螨(binapacryl),硫酸二(甲基汞)(bis(methylmercury)sulfate),氧化二(三丁基锡)(bis(tributyltin)oxide),丁硫啶(buthiobate),草菌盐(cadmium calcium copper zinc chromate sulfate),吗菌威(carbamorph),氰粉灵(CECA),灭瘟唑(chlobenthiazone),双胺灵(chloraniformethan),苯咪唑菌(chlorfenazole),四氯喹噁啉(chlorquinox),咪菌酮(climbazole),二(3-苯基水杨酸)铜(copper bis(3-phenylsalicylate)),铬酸铜锌(copper zinc chromate),硫杂灵(cufraneb),硫酸肼铜(cupric hydrazinium sulfate),福美铜氯(cuprobam),环糠酰胺(cyclafuramid),氰菌灵(cypendazole),酯菌胺(cyprofuram),癸磷锡(decafentin),二氯萘醌(dichlone),菌核利(dichlozoline),苄氯三唑醇(diclobutrazol),甲菌定(dimethirimol),敌螨通(dinocton),硝辛酯(dinosulfon),硝丁酯(dinoterbon),吡菌硫(dipyrithione),灭菌磷(ditalimfos),多敌菌(dodicin),敌菌酮(drazoxolon),稻瘟净(EBP),枯瘟净(ESBP),乙环唑(etaconazole),代森硫(etem),乙嘧酚(ethirim),敌磺钠(fenaminosulf),咪菌腈(fenapanil),种衣酯(fenitropan),三氟苯唑(fluotrimazole),灭菌胺(furcarbanil),呋菌唑(furconazole),顺式呋菌唑(furconazole-cis),拌种胺(furmecyclox),呋菌隆(furophanate),果绿啶(glyodine),灰黄霉素(griseofulvin),丙烯酸喹啉酯(halacrinate),噻茂铜(Hercules 3944),环己硫磷(hexylthiofos),丙环啶菌(ICIA0858),壬氧磷胺(isopamphos),氯苯咪菌酮(isovaledione),邻酰胺(mebenil),咪卡病西(mecarbinzid),肼叉噁唑酮(metazoxolon),呋菌胺(methfuroxam),氰胍甲汞(methylmercury dicyandiamide),噻菌胺(metsulfovax),代森环(milneb),粘氯酸酐(mucochloric anhydride),甲菌利(myclozolin),N-3,5-二氯苯基琥珀酰亚胺(N-3,5-dichlorophenylsuccinimide),N-3-硝基苯基衣康酰亚胺(N-3-nitrophenylitaconimide),多马霉素(natamycin),N-乙基汞基-4-甲苯磺酰苯胺(N-ethylmercurio-4-toluenesulfonanilide),二(二甲基二硫代氨基甲酸)镍(nickel bis(dimethyldithiocarbamate)),八氯酮(OCH),二甲基二硫代氨基甲酸苯汞(phenylmercurydimethyldithiocarbamate),硝酸苯汞(phenylmercury nitrate),氯瘟磷(phosdiphen),硫菌威(prothiocarb);盐酸硫菌威(prothiocarb hydrochloride),吡喃灵(pyracarbolid),啶菌腈(pyridinitril),吡氧氯(pyroxychlor),氯吡呋醚(pyroxyfur),5-乙酰基-8-羟基喹啉(quinacetol);5-乙酰基-8-羟基喹啉硫酸盐(quinacetolsulfate),酯菌腙(quinazamid),喹唑菌酮(quinconazole),吡咪唑菌(rabenzazole),水杨酰胺(salicylanilide),唑菌庚醇(SSF-109,戊苯砜(sultropen),福代硫(tecoram),噻二氟(thiadifluor),噻菌腈(thicyofen),苯菌胺(thiochlorfenphim),硫菌灵(thiophanate),克杀螨(thioquinox),硫氰苯甲酰胺(tioxymid),三唑磷胺(triamiphos),嘧菌醇(triarimol),叶锈特(triazbutil),水杨菌胺(trichlamide),福美甲胂(urbacid),灭杀威(zarilamid),及其任何组合。
此外,本申请所述的化合物可与其它杀生物剂结合,包括杀虫剂、杀线虫剂、杀螨剂、杀节肢动物剂(arthropodicide)、杀细菌剂或它们的组合,所述其它杀生物剂在就应用所选的介质中与本申请化合物相容并且不拮抗本申请化合物的活性以形成杀虫混合物和它们的协同混合物。本申请的杀真菌化合物通常与一种或多种其它杀生物剂联合施用,从而防治更宽范围的不期望害虫。当与其它杀生物剂联合施用时,本申请要求保护的化合物可与一种或多种其它杀生物剂配制在一起、可与一种或多种其它杀生物剂桶混(tank mix)在一起或可与一种或多种其它杀生物剂顺序施用。常见的杀虫剂包括但不限于:1,2-二氯丙烷(1,2-dichloropropane)、阿维菌素(abamectin)、高灭磷(acephate)、吡虫清(acetamiprid)、家蝇磷(acethion)、乙酰虫腈(acetoprole)、氟酯菊酯(acrinathrin)、丙烯腈(acrylonitrile)、棉铃威(alanycarb)、涕灭威(aldicarb)、砜灭威(aldoxycarb)、艾氏剂(aldrin)、丙烯除虫菊(allethrin)、阿洛氨菌素(allosamidin)、除害威(allyxycarb)、α-氯氰菊酯(alpha-cypermethrin)、α-蜕皮素(alpha-ecdysone)、α-硫丹(alpha-endosulfan)、赛果(amidithion)、灭害威(aminocarb)、胺吸磷(amiton)、草酸胺吸磷(amiton oxalate)、虫螨脒(amitraz)、新烟碱(anabasine)、艾噻达松(athidathion)、艾扎丁(azadirachtin)、唑啶磷(azamethiphos)、益棉磷(azinphos-ethyl)、保棉磷(azinphos-methyl)、偶氮磷(azothoate)、六氟硅酸钡(barium hexafluorosilicate)、熏虫菊(barthrin)、唑虫威(bendiocarb)、丙硫克拜威(benfuracarb)、杀虫磺(bensultap)、β-氟氯氰菊酯(beta-cyfluthrin)、β-氯氰菊酯(beta-cypermethrin)、联苯菊酯(bifenthrin)、反式丙烯除虫菊(bioallethrin)、bioethanomethrin、生物氯菊酯(biopermethrin)、双二氟虫脲(bistrifluron)、硼砂(borax)、硼酸(boric acid)、溴苯烯磷(bromfenvinfos)、溴烯杀(bromocyclen)、溴-DDT、溴硫磷(bromophos)、乙基溴硫磷(bromophos-ethyl)、合杀威(bufencarb)、噻嗪酮(buprofezin)、畜虫威(butacarb)、特嘧硫磷(butathiofos)、丁叉威(butocarboxim)、丁酯磷(butonate)、氧丁叉威(butoxycarboxim)、硫线磷(cadusafos)、砷酸钙(calcium arsenate)、石硫合剂(calciumpolysulfide)、毒杀芬(camphechlor)、氯灭杀威(carbanolate)、甲萘威(carbaryl)、虫螨威(carbofuran)、二硫化碳(carbon disulfide)、四氯化碳(carbon tetrachloride)、三硫磷(carbophenothion)、丁硫克百威(carbosulfan)、巴丹(cartap)、盐酸巴丹(cartaphydrochloride)、氯虫酰胺(chlorantraniliprole)、冰片丹(chlorbicyclen)、氯丹(chlordane)、开蓬(chlordecone)、氯苯脒(chlordimeform)、盐酸氯苯脒(chlordimeformhydrochloride)、壤土氯磷(chlorethoxyfos)、氟唑虫清(chlorfenapyr)、毒虫畏(chlorfenvinphos)、定虫隆(chlorfluazuron)、氯甲磷(chlormephos)、氯仿(chloroform)、氯化苦(chloropicrin)、氯腈肟磷(chlorphoxim)、氯吡唑磷(chlorprazophos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、氯甲硫磷(chlorthiophos)、环虫酰胺(chromafenozide)、瓜菊酯I(cinerin I)、瓜菊酯I(cinerinII)、瓜菊酯(cinerins)、左旋反灭虫菊酯(cismethrin)、除线威(cloethocarb)、氯氰碘柳胺(closantel)、噻虫胺(clothianidin)、乙酰亚砷酸铜(copper acetoarsenite)、砷酸铜(copper arsenate)、环烷酸铜(copper naphthenate)、油酸铜(copper oleate)、库马磷(coumaphos)、畜虫磷(coumithoate)、克罗米通(crotamiton)、丁烯磷(crotoxyphos)、育畜磷(crufomate)、氟铝酸钠(cryolite)、苯腈磷(cyanofenphos)、杀螟磷(cyanophos)、果虫磷(cyanthoate)、氰虫酰胺(cyantraniliprole)、环戊烯菊酯(cyclethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、三氟氯氰菊酯(cyhalothrin)、氯氰菊酯(cypermethrin)、苯醚氰菊酯(cyphenothrin)、灭蝇胺(cyromazine)、赛灭磷(cythioate)、DDT、一甲呋喃丹(decarbofuran)、溴氰菊酯(deltamethrin)、田乐磷(demephion)、田乐磷-O(demephion-O)、田乐磷-S(demephion-S)、内吸磷(demeton)、甲基内吸磷(demeton-methyl)、内吸磷-O(demeton-O)、内吸磷-O-甲基(demeton-O-methyl)、内吸磷-S(demeton-S)、内吸磷-S-甲基(demeton-S-methyl)、内吸磷-S-甲基硫(demeton-S-methylsulphon)、杀螨硫隆(diafenthiuron)、氯亚磷(dialifos)、硅藻土(diatomaceous earth)、二嗪农(diazinon)、异氯硫磷(dicapthon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos)、N-(3-甲基苯基)氨基甲酸甲酯(dicresyl)、百治磷(dicrotophos)、环虫腈(dicyclanil)、狄氏剂(dieldrin)、氟脲杀(diflubenzuron)、丙羟茶碱(dilor)、四氟甲醚菊酯(dimefluthrin)、甲氟磷(dimefox)、地麦威(dimetan)、乐果(dimethoate)、苄菊酯(dimethrin)、甲基毒虫畏(dimethylvinphos)、敌蝇威(dimetilan)、消螨酚(dinex)、dinex-diclexine、丙硝酚(dinoprop)、戊硝酚(dinosam)、呋虫胺(dinotefuran)、噁茂醚(diofenolan)、杀抗松(dioxabenzofos)、二氧威(dioxacarb)、敌噁磷(dioxathion)、乙拌磷(disulfoton)、噻喃磷(dithicrofos)、右旋柠檬烯(d-limonene)、二硝甲酚(DNOC)、二硝甲酚-铵、二硝甲酚-钾、二硝甲酚-钠、多拉克汀(doramectin)、促蜕皮甾酮(ecdysterone)、甲氨基阿维菌素(emamectin)、苯甲酸甲氨基阿维菌素(emamectin benzoate)、多杀威(EMPC)、烯炔菊酯(empenthrin)、硫丹(endosulfan)、因毒磷(endothion)、异狄氏剂(endrin)、苯硫磷(EPN)、保幼醚(epofenonane)、爱普瑞菌素(eprinomectin)、Es-生物烯丙菊酯(esdepalléthrine)、高氰戊菊酯(esfenvalerate)、etaphos、苯虫威(ethiofencarb)、乙硫磷(ethion)、乙虫腈(ethiprole)、益果(ethoate-methyl)、灭克磷(ethoprophos)、甲酸乙酯(ethyl formate)、乙基-DDD、1,2-二溴乙烷(ethylene dibromide)、1,2-二氯乙烷(ethylene dichloride)、环氧乙烷(ethylene oxide)、醚菊酯(etofenprox)、乙嘧硫磷(etrimfos)、EXD、氨磺磷(famphur)、克线磷(fenamiphos)、抗螨唑(fenazaflor)、皮蝇磷(fenchlorphos)、乙苯威(fenethacarb)、五氟苯菊酯(fenfluthrin)、杀螟硫磷(fenitrothion)、丁苯威(fenobucarb)、fenoxacrim、双氧威(fenoxycarb)、吡氯氰菊酯(fenpirithrin)、甲氰菊酯(fenpropathrin)、丰索磷(fensulfothion)、倍硫磷(fenthion)、倍硫磷-乙基(fenthion-ethyl)、氰戊菊酯(fenvalerate)、锐劲特(fipronil)、氟啶虫酰胺(flonicamid)、氟虫酰胺(flubendiamide)、氟氯双苯隆(flucofuron)、氟螨脲(flucycloxuron)、氟氰菊酯(flucythrinate)、嘧虫胺(flufenerim)、氟虫脲(flufenoxuron)、氟丙苄醚(flufenprox)、氟胺氰菊酯(fluvalinate)、地虫磷(fonofos)、伐虫脒(formetanate)、盐酸伐虫脒(formetanatehydrochloride)、安果(formothion)、胺甲威(formparanate)、盐酸胺甲威(formparanatehydrochloride)、丁苯硫磷(fosmethilan)、甲基毒死蜱(fospirate)、伐线丹(fosthietan)、呋线威(furathiocarb)、糠醛菊酯(furethrin)、γ-三氟氯氰菊酯(gamma-cyhalothrin)、γ-HCH、卤醚菊酯(halfenprox)、特丁苯酰肼(halofenozide)、HCH、HEOD、七氯(heptachlor)、庚虫磷(heptenophos)、速杀硫磷(heterophos)、氟铃脲(hexaflumuron)、艾氏剂(HHDN)、灭蚁腙(hydramethylnon)、氰化氢(hydrogen cyanide)、蒙五一二(hydroprene)、喹啉威(hyquincarb)、吡虫啉(imidacloprid)、咪炔菊酯(imiprothrin)、茚虫威(indoxacarb)、碘甲烷(iodomethane)、丰丙磷(IPSP)、氯唑磷(isazofos)、碳氯灵(isobenzan)、水胺硫磷(isocarbophos)、异艾氏剂(isodrin)、丙胺磷(isofenphos)、丙胺磷-甲基(isofenphos-methyl)、异丙威(isoprocarb)、稻瘟灵(isoprothiolane)、叶蚜磷(isothioate)、噁唑磷(isoxathion)、齐墩螨素(ivermectin)、茉莉菊酯I(jasmolin I)、茉莉菊酯II(jasmolin II)、碘硫磷(jodfenphos)、保幼激素I(juvenile hormone I)、保幼激素II(juvenile hormone II)、保幼激素III(juvenile hormone III)、克来范(kelevan)、蒙七七七(kinoprene)、λ-三氟氯氰菊酯(lambda-cyhalothrin)、砷酸铅(lead arsenate)、lepimectin、溴苯磷(leptophos)、林丹(lindane)、啶虫磷(lirimfos)、氟丙氧脲(lufenuron)、噻唑磷(lythidathion)、马拉硫磷(malathion)、苄丙二腈(malonoben)、叠氮磷(mazidox)、灭蚜磷(mecarbam)、甲基灭蚜磷(mecarphon)、灭蚜松(menazon)、二噻磷(mephosfolan)、氯化亚汞(mercurous chloride)、甲亚砜磷(mesulfenfos)、氰氟虫腙(metaflumizone)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、灭虫威(methiocarb)、丁烯胺磷(methocrotophos)、灭多虫(methomyl)、蒙五一五(methoprene)、甲氧滴滴涕(emthoxychlor)、甲氧苯酰肼(methoxyfenozide)、溴甲烷(methyl bromide)、异硫氰酸甲酯(methyl isothiocyanate)、甲基氯仿(methylchloroform)、二氯甲烷(methylene chloride)、氧卞氟菊酯(metofluthrin)、速灭威(metolcarb)、噁虫酮(metoxadiazone)、速灭磷(mevinphos)、自克威(mexacarbate)、米尔螨素(milbemectin)、米尔贝肟(milbemycin oxime)、丙胺氟磷(mipafox)、灭蚁灵(mirex)、molosultap、久效磷(monocrotophos)、杀虫单(monomehypo)、杀虫单(monosultap)、茂果(morphothion)、莫西克丁(moxidectin)、萘肽磷(naftalofos)、二溴磷(naled)、萘(naphthalene)、烟碱(nicotine)、氟蚁灵(nifluridide)、硝胺烯啶(nitenpyram)、硝虫噻嗪(nithiazine)、腈叉威(nitrilacarb)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氧乐果(omethoate)、甲氨叉威(oxamyl)、砜吸磷(oxydemeton-methyl)、异砜磷(oxydeprofos)、砜拌磷(oxydisulfoton)、对-二氯苯(para-dichlorobenzene)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、氟幼脲(penfluron)、五氯酚(pentachlorophenol)、苄氯菊脂(permethrin)、芬硫磷(phenkapton)、苯醚菊酯(phenothrin)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、棉安磷(phosfolan)、亚胺硫磷(phosmet)、对氯硫磷(phosnichlor)、磷胺(phosphamidon)、磷化氢(phosphine)、肟硫磷(phoxim)、甲基肟硫磷(phoxim-methyl)、甲胺嘧磷(pirimetaphos)、抗蚜威(pirimicarb)、乙基虫螨磷(pirimiphos-ethyl)、甲基虫螨磷(pirimiphos-methyl)、亚砷酸钾(potassium arsenite)、硫氰酸钾(potassium thiocyanate)、pp′-DDT、炔酮菊酯(prallethrin)、早熟素I(precocene I)、早熟素II(precocene II)、早熟素III(precocene III)、酰胺嘧啶啉(primidophos)、丙溴磷(profenofos)、环丙氟灵(profluralin)、蜱虱威(promacyl)、猛杀威(promecarb)、丙虫磷(propaphos)、烯虫磷(propetamphos)、残杀威(propoxur)、乙噻唑磷(prothidathion)、丙硫磷(prothiofos)、发果(prothoate)、protrifenbute、吡唑硫磷(pyraclofos)、嘧啶威(pyrafluprole)、吡菌磷(pyrazophos)、反灭虫菊(pyresmethrin)、除虫菊酯I(pyrethrin I)、除虫菊酯II(pyrethrin II)、除虫菊(pyrethrins)、哒螨酮(pyridaben)、啶虫丙醚(pyridalyl)、打杀磷(pyridaphenthion)、pyrifluquinazon、嘧胺苯醚(pyrimidifen)、嘧啶磷(pyrimitate)、吡啶醇(pyriprole)、蚊蝇醚(pyriproxyfen)、苦木(quassia)、喹噁啉(quinalphos)、甲基喹噁啉(quinalphos-methyl)、喹塞昂(quinothion)、碘醚柳胺(rafoxanide)、苄呋菊酯(resmethrin)、鱼藤酮(rotenone)、鱼泥汀(ryania)、沙巴草(sabadilla)、八甲磷(schradan)、赛拉菌素(selamectin)、灭虫硅醚(silafluofen)、硅胶(silica gel)、亚砷酸钠(sodium arsenite)、氟化钠(sodium fluoride)、六氟硅酸钠(sodiumhexafluorosilicate)、硫氰酸钠(sodium thiocyanate)、苏果(sophamide)、多虫菌素(spinetoram)、艾克敌(spinosad)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat)、磺苯醚隆(sulcofuron)、磺苯醚隆钠(sulcofuron-sodium)、氟虫胺(sulfluramid)、硫特普(sulfotep)、氟啶虫胺腈(sulfoxaflor)、氟化硫(sulfuryl fluoride)、乙丙硫磷(sulprofos)、τ-氟胺氰菊酯(tau-fluvalinate)、噻螨威(tazimcarb)、滴滴滴(TDE)、双苯酰肼(tebufenozide)、吡螨胺(tebufenpyrad)、嘧丙磷(tebupirimfos)、伏虫隆(teflubenzuron)、七氟菊酯(tefluthrin)、双硫磷(temephos)、特普(TEPP)、环戊烯丙菊酯(terallethrin)、特丁磷(terbufos)、四氯乙烷(tetrachloroethane)、杀虫畏(tetrachlorvinphos)、胺菊酯(tetramethrin)、tetramethylfluthrin、θ-氯氰菊酯(theta-cypermethrin)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、噻氯磷(thicrofos)、抗虫威(thiocarboxime)、硫环杀(thiocyclam)、草酸硫环杀(thiocyclamoxalate)、硫双灭多威(thiodicarb)、特氨叉威(thiofanox)、甲基乙拌磷(thiometon)、杀虫双(thiosultap)、杀虫双-二钠(thiosultap-disodium)、杀虫双-单钠(thiosultap-monosodium)、敌贝特(thuringiensin)、唑虫酰胺(tolfenpyrad)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、反氯菊酯(transpermethrin)、苯螨噻(triarathene)、醚苯磺隆(triazamate)、三唑磷(triazophos)、敌百虫(trichlorfon)、异皮蝇磷(trichlormetaphos-3)、壤虫磷(trichloronat)、氯苯乙丙磷(trifenofos)、杀虫隆(triflumuron)、混杀威(trimethacarb)、硫烯酸酯(triprene)、蚜灭多(vamidothion)、氟吡唑虫(vaniliprole)、二甲威(XMC)、灭杀威(xylylcarb)、ζ-氯氰菊酯(zeta-cypermethrin)、zolaprofos和它们的任意组合。
此外,本申请所述的化合物可在就应用所选的介质中与本申请化合物相容并且不拮抗本申请化合物活性的除草剂结合以形成杀虫混合物和它们的协同混合物。本申请的杀真菌化合物通常与一种或多种除草剂联合施用,从而防治更宽范围的不期望植物。当与除草剂联合施用时,本申请要求保护的化合物可与一种或多种除草剂配制在一起、可与一种或多种除草剂桶混(tank mix)在一起或可与一种或多种除草剂顺序施用。常见的除草剂包括但不限于:4-CPA;4-CPB;4-CPP;2,4-D;3,4-DA;2,4-DB;3,4-DB;2,4-DEB;2,4-DEP;3,4-DP;2,3,6-TBA;2,4,5-T;2,4,5-TB;刈草胺(acetochlor)、三氟羧草醚(acifluorfen)、苯草醚(aclonifen)、丙烯醛(acrolein)、甲草胺(alachlor)、草毒死(allidochlor)、禾草灭(alloxydim)、烯丙醇(allyl alcohol)、五氯戊酮酸(alorac)、特津酮(ametridione)、莠灭净(ametryn)、特草嗪酮(amibuzin)、氨唑草酮(amicarbazone)、磺氨磺隆(amidosulfuron)、环丙嘧啶酸(aminocyclopyrachlor)、氯氨基吡啶酸(aminopyralid)、甲基胺草磷(amiprofos-methyl)、杀草强(amitrole)、氨基磺酸铵(ammonium sulfamate)、莎稗磷(anilofos)、疏草隆(anisuron)、磺草灵(asulam)、莠去通(atraton)、莠去津(atrazine)、唑啶炔草(azafenidin)、四唑磺隆(azimsulfuron)、叠氮净(aziprotryne)、燕麦灵(barban)、BCPC、氟丁酰草胺(beflubutamid)、草除灵(benazolin)、bencarbazone、氟草胺(benfluralin)、呋草磺(benfuresate)、苄嘧磺隆(bensulfuron)、地散磷(bensulide)、灭草松(bentazone)、胺酸杀(benzadox)、双苯嘧草酮(benzfendizone)、苄草胺(benzipram)、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、氟磺胺草(benzofluor)、新燕灵(benzoylprop)、噻草隆(benzthiazuron)、bicyclopyrone、治草醚(bifenox)、双丙氨酰膦(bilanafos)、双嘧苯甲酸(bispyribac)、硼砂(borax)、除草定(bromacil)、糠草腈(bromobonil)、溴丁酰草胺(bromobutide)、杀草全(bromofenoxim)、溴苯腈(bromoxynil)、杀莠敏(brompyrazon)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草膦(butamifos)、丁烯草胺(butenachlor)、特咪唑草(buthidazole)、丁噻隆(buthiuron)、地乐胺(butralin)、丁苯草酮(butroxydim)、炔草隆(buturon)、苏达灭(butylate)、二甲胂酸(cacodylic acid)、苯酮唑(cafenstrole)、氯酸钙(calciumchlorate)、氰氨化钙(calcium cyanamide)、克草胺酯(cambendichlor)、卡巴草灵(carbasulam)、长杀草(carbetamide)、特噁唑威(carboxazole)、草败死(chlorprocarb)、氟酮唑草(carfentrazone)、CDEA、CEPC、氯硝醚(chlomethoxyfen)、草灭平(chloramben)、丁酰草胺(chloranocryl)、炔禾灵(chlorazifop)、炔禾灵(chlorazifop)、可乐津(chlorazine)、氯溴隆(chlorbromuron)、氯炔灵(chlorbufam)、乙氧苯隆(chloreturon)、伐草克(chlorfenac)、燕麦酯(chlorfenprop)、氟嘧杀(chlorflurazole)、氯甲丹(chlorflurenol)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、草枯醚(chlornitrofen)、三氯丙酸(chloropon)、氯麦隆(chlorotoluron)、枯草隆(chloroxuron)、羟敌草腈(chloroxynil)、氯苯胺灵(chlorpropham)、绿磺隆(chlorsulfuron)、氯酞酸(chlorthal)、草克乐(chlorthiamid)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、咯草隆(cisanilide)、烯草酮(clethodim)、碘氯啶酯(cliodinate)、炔草酯(clodinafop)、氯丁草(clofop)、异噁草酮(clomazone)、稗草胺(clomeprop)、调果酸(cloprop)、环丁烯草酮(cloproxydim)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam)、CMA、硫酸铜(copper sulfate)、CPMF、CPPC、醚草敏(credazine)、甲酚(cresol)、苄草隆(cumyluron)、氰草净(cyanatryn)、氰草津(cyanazine)、草灭特(cycloate)、环丙磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、环莠隆(cycluron)、氰氟草酯(cyhalofop)、牧草快(cyperquat)、环丙津(cyprazine)、三环塞草胺(cyprazole)、环酰草胺(cypromid)、香草隆(daimuron)、茅草枯(dalapon)、棉隆(dazomet)、敌草乐(delachlor)、甜菜安(desmedipham)、敌草净(desmetryn)、燕麦敌(di-allate)、麦草畏(dicamba)、敌草腈(dichlobenil)、氯全隆(dichloralurea)、苄胺灵(dichlormate)、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、氯甲草(diclofop)、唑嘧磺胺(diclosulam)、二乙除草双(diethamquat)、安塔(diethatyl)、氟苯戊烯酸(difenopenten)、枯莠隆(difenoxuron)、苯敌快(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、克草胺(dimethachlor)、戊草津(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-P)、敌灭生(dimexano)、敌米达松(dimidazon)、敌乐胺(dinitramine)、地乐特(dinofenate)、丙硝酚(dinoprop)、戊硝酚(dinosam)、地乐酚(dinoseb)、特乐酚(dinoterb)、草乃敌(diphenamid)、杀草净(dipropetryn)、敌草快(diquat)、2,4-滴硫酸(disul)、氟硫草定(dithiopyr)、敌草隆(diuron)、DMPA、DNOC、DSMA、EBEP、甘草津(eglinazine)、草藻灭(endothal)、磺唑草(epronaz)、EPTC、抑草蓬(erbon)、禾草畏(esprocarb)、丁氟消草(ethalfluralin)、胺苯磺隆(ethametsulfuron)、噻二唑隆(ethidimuron)、抑草威(ethiolate)、乙呋草磺(ethofumesate)、氯氟草醚(ethoxyfen)、乙氧嘧磺隆(ethoxysulfuron)、硝草酚(etinofen)、乙胺草醚(etnipromid)、乙氧苯酰草(etobenzanid)、EXD、酰苯磺威(fenasulam)、2,4,5-涕丙酸(fenoprop)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、fenoxasulfone、氯苯氧乙醇(fenteracol)、噻唑禾草灵(fenthiaprop)、四唑草胺(fentrazamide)、非草隆(fenuron)、硫酸亚铁(ferrous sulfate)、氟燕灵(flamprop)、强氟燕灵(flamprop-M)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、异丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone)、氟吡磺隆(flucetosulfuron)、氟消草(fluchloralin)、氟噻草胺(flufenacet)、氟苯吡草(flufenican)、氟哒嗪草酯(flufenpyr)、氟唑啶草(flumetsulam)、三氟噁嗪(flumezin)、氟烯草酸(flumiclorac)、丙炔氟草胺(flumioxazin)、炔草胺(flumipropyn)、伏草隆(fluometuron)、消草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen)、唑啶草(fluoromidine)、氟除草醚(fluoronitrofen)、氟苯隆(fluothiuron)、氟胺草唑(flupoxam)、flupropacil、四氟丙酸(flupropanate)、氟啶磺隆(flupyrsulfuron)、氟草同(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、呋草酮(flurtamone)、达草氟(fluthiacet)、氟磺胺草醚(fomesafen)、甲酰胺磺隆(foramsulfuron)、膦铵素(fosamine)、氟呋草醚(furyloxyfen)、草丁膦(glufosinate)、草铵膦(glufosinate-P)、草甘膦(glyphosate)、氟氯吡啶酯(halauxifen),氟硝磺酰胺(halosafen)、吡氯磺隆(halosulfuron)、卤草定(haloxydine)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、六氯丙酮(hexachloroacetone)、六氟胂酸盐(hexaflurate)、六嗪酮(hexazinone)、咪草酯(imazamethabenz)、咪草啶酸(imazamox)、甲咪唑烟酸(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr)、啶咪磺隆(imazosulfuron)、茚草酮(indanofan)、indaziflam、碘草腈(iodobonil)、碘甲烷(iodomethane)、碘磺隆(iodosulfuron)、碘苯腈(ioxynil)、抑草津(ipazine)、ipfencarbazone、丙草定(iprymidam)、丁咪胺(isocarbamid)、异草定(isocil)、丁嗪草酮(isomethiozin)、异草完隆(isonoruron)、氮草(isopolinate)、异丙乐灵(isopropalin)、异丙隆(isoproturon)、异恶隆(isouron)、异噁酰草胺(isoxaben)、异噁氯草酮(isoxachlortole)、异噁氟草酮(isoxaflutole)、噁草醚(isoxapyrifop)、特胺灵(karbutilate)、ketospiradox、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、甲基胂酸(MAA)、甲胂一铵(MAMA)、2甲4氯(MCPA)、酚硫杀(MCPA-thioethyl)、2甲4氯丁酸(MCPB)、2甲4氯丙酸(mecoprop)、精2甲4氯丙酸(mecoprop-P)、丁硝酚(medinoterb)、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、灭莠津(mesoprazine)、甲基二磺隆(mesosulfuron)、甲基磺草酮(mesotrione)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、氟哒草(metflurazon)、噻唑隆(methabenzthiazuron)、氟烯硝草(methalpropalin)、灭草定(methazole)、甲硫苯威(methiobencarb)、methiozolin、灭草恒(methiuron)、醚草通(methometon)、盖草津(methoprotryne)、溴甲烷(methyl bromide)、异硫氰酸甲酯(methyl isothiocyanate)、苯丙隆(methyldymron)、色满隆(metobenzuron)、秀谷隆(metobromuron)、异丙甲草胺(metolachlor)、唑草磺胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、甲磺隆(metsulfuron)、草达灭(molinate)、庚酰草胺(monalide)、特噁唑隆(monisouron)、单氯代乙酸(monochloroacetic acid)、绿谷隆(monolinuron)、灭草隆(monuron)、伐草快(morfamquat)、甲胂一钠(MSMA)、萘丙胺(naproanilide)、敌草胺(napropamide)、萘草胺(naptalam)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、吡氯草胺(nipyraclofen)、甲磺乐灵(nitralin)、除草醚(nitrofen)、三氟甲草醚(nitrofluorfen)、达草灭(norflurazon)、草完隆(noruron)、八氯酮(OCH)、坪草丹(orbencarb)、邻-二氯苯(ortho-dichlorobenzene)、orthosulfamuron、黄草消(oryzalin)、炔丙噁唑草(oxadiargyl)、噁草灵(oxadiazon)、噁杀草敏(oxapyrazon)、环丙氧磺隆(oxasulfuron)、氯噁嗪草(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、对伏隆(parafluron)、百草枯(paraquat)、克草猛(pebulate)、壬酸(pelargonic acid)、胺硝草(pendimethalin)、五氟磺草胺(penoxsulam)、五氯酚(pentachlorophenol)、甲氯酰草胺(pentanochlor)、戊噁唑草(pentoxazone)、氟草磺胺(perfluidone)、烯草胺(pethoxamid)、棉胺宁(phenisopham)、甜菜宁(phenmedipham)、甜菜宁-乙基(phenmedipham-ethyl)、稀草隆(phenobenzuron)、乙酸苯汞(phenylmercury acetate)、氨氯吡啶酸(picloram)、氟吡草胺(picolinafen)、pinoxaden、哌草磷(piperophos)、亚砷酸钾(potassium arsenite)、叠氮化钾(potassiumazide)、氰酸钾(potassium cyanate)、冰草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、环氰津(procyazine)、氨氟乐灵(prodiamine)、氟唑草胺(profluazol)、环丙氟灵(profluralin)、环苯草酮(profoxydim)、丙草止津(proglinazine)、扑灭通(prometon)、扑草净(prometryn)、毒草安(propachlor)、敌稗(propanil)、喔草酯(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、嗪咪唑嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、磺亚胺草(prosulfalin)、苄草丹(prosulfocarb)、氟丙磺隆(prosulfuron)、扑灭生(proxan)、广草胺(prynachlor)、比达农(pydanon)、双唑草腈(pyraclonil)、氟唑草酯(pyraflufen)、pyrasulfotole、吡唑特(pyrazolynate)、吡嘧磺隆(pyrazosulfuron)、苄草唑(pyrazoxyfen)、嘧苯草肟(pyribenzoxim)、稗草丹(pyributicarb)、氯草定(pyriclor)、pyridafol、哒草特(pyridate)、环酯草醚(pyriftalid)、肟啶草(pyriminobac)、pyrimisulfan、嘧硫草醚(pyrithiobac)、pyroxasulfone、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、氯藻胺(quinonamid)、喹禾灵(quizalofop)、精喹禾灵(quizalofop-P)、硫氰苯乙胺(rhodethanil)、玉嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、S-异丙甲草胺(S-metolachlor)、另丁津(sebuthylazine)、密草通(secbumeton)、稀禾定(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西玛通(simeton)、西草净(simetryn)、氯乙酸(SMA)、亚砷酸钠(sodium arsenite)、叠氮化钠(sodium azide)、氯酸钠(sodium chlorate)、磺草酮(sulcotrione)、草克死(sulfallate)、磺胺草唑(sulfentrazone)、嘧磺隆(sulfometuron)、乙磺磺隆(sulfosulfuron)、硫酸(sulfuric acid)、吖庚磺酯(sulglycapin)、灭草灵(swep)、三氯醋酸(TCA)、牧草胺(tebutam)、丁唑隆(tebuthiuron)、tefuryltrione、tembotrione、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、猛杀草(terbuchlor)、甲氧去草净(terbumeton)、特丁津(terbuthylazine)、去草净(terbutryn)、氟氧隆(tetrafluron)、噻醚草胺(thenylchlor)、赛唑隆(thiazafluron)、噻草啶(thiazopyr)、噻二唑胺(thidiazimin)、赛二唑素(thidiazuron)、噻酮磺隆-甲基(thiencarbazone-methyl)、噻磺隆(thifensulfuron)、禾草丹(thiobencarb)、丁草威(tiocarbazil)、嘧草胺(tioclorim)、topramezone、苯草酮(tralkoxydim)、triafamone、野麦畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、杀草畏(tricamba)、三氯吡氧乙酸(triclopyr)、灭草环(tridiphane)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、三氟苯氧丙酸(trifop)、三氟禾草肟(trifopsime)、三羟基三嗪(trihydroxytriazine)、三甲隆(trimeturon)、茚草酮(tripropindan)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、灭草猛(vernolate)、和二甲苯草胺(xylachlor)。
本申请另一种实施方式为用于防治或预防真菌侵袭的方法。该方法包括向土壤、植物、根、叶子、或真菌所在地(locus)或向要预防感染(infestation)的所在地(例如施用至谷物或葡萄植物)施用杀真菌有效量的一种多种式I化合物。所述化合物适于在抗真菌水平处理各种植物,同时表现出低植物毒性。所述化合物可以用于保护剂和/或铲除剂方式二者中。
发现所述化合物具有显著的杀真菌作用,特别是用于农业用途。多种所述化合物特别有效用于农业作物和园艺植物。
本领域技术人员理解的是,所述化合物针对前述真菌的效力确立了所述化合物作为杀真菌剂的一般效用。
所述化合物具有宽的抗真菌病原体(fungicidal pathogen)活性的范围。示例性病原体可包括但不限于以下病害的引发剂(causing agent):小麦斑枯病(wheat leafblotch)(小麦发酵壳针孢(Zymoseptoria tritici)),小麦褐锈病(wheat brown rust)(小麦叶锈菌(Puccinia triticina)),小麦条锈病(wheat stripe rust)(小麦条锈菌(Puccinia striiformis)),苹果黑星病(scab of apple)(苹果黑星病菌(Venturiainaequalis)),葡萄白粉病(powdery mildew of grapevine)(葡萄白粉病(Uncinulanecator)),大麦烫伤(barley scald)(大麦云纹病菌(Rhynchosporium secalis)),稻瘟病(blast of rice)(稻瘟病菌(Pyricularia oryzae)),大豆锈病(rust of soybean)(豆薯层锈菌(Phakopsora pachyrhizi)),小麦颖枯病(glume blotch of wheat)(小麦颖枯病菌(Leptosphaeria nodorum)),小麦白粉病(powdery mildew of wheat)(小麦白粉菌(Blumeria graminis f.sp.tritici)),大麦白粉病(powdery mildew of barley)(大麦白粉病菌(Blumeria graminis f.sp.hordei)),瓜类白粉病(powdery mildew ofcucurbits)(黄瓜白粉病(Erysiphe cichoracearum)),瓜类炭疽病(Anthracnose ofcucurbits)(瓜类炭疽病菌(Colletotrichum lagenarium)),甜菜褐斑病(leaf spot ofbeet)(甜菜尾孢菌(Cercospora beticola)),番茄绵疫病(early blight of eggplant)(番茄早疫病菌(Alternaria solani)),和大麦斑枯(spot blotch of barley)(禾旋孢腔菌(Cochliobolus sativus))。所施用的活性物质的确切量不仅依赖于所施用的具体活性物质而且还依赖于所需的具体作用、所防治的真菌种类及其生长阶段,以及将与所述化合物接触的植物的部分或其它产物。因此,所有化合物和含有所述化合物的制剂在相似浓度时可能不是同等有效的或不能抗相同种类的真菌。
所述化合物以病害抑制和植物学可接受的量有效用于植物。术语″病害抑制和植物学可接受的量″是指杀死或抑制植物病害(希望对其进行防治)但对植物不是明显具有毒性的化合物的量。该量通常为约0.1至约1000ppm(份每百万份),优选的是1至500ppm。所需化合物的确切浓度随所防治的真菌病害、所采用的制剂类型、施用方法、具体植物种类、气候条件等变化。合适的施用率通常在约0.10至约4磅/英亩(约0.01至0.45克/平方米,g/m2)范围内。
可将本文所给出的任意范围或所需值进行扩展或改变而不丧失所寻求的作用,这一点对技术人员理解本文教导内容来说是显而易见的。
式I化合物可使用公知的化学方法制备。在本说明书没有专门提及的中间体是商购的、可通过化学文献中披露的路线制备或可容易地使用标准方法由商业起始物质合成。
一般方案
以下方案说明生成式(I)的吡啶酰胺化合物的方法。以下说明书和实施例用于说明目的,不应将其理解为对取代基或取代类型的限制。
式1.1、1.2、1.3、1.5、1.6、和1.8的化合物(其中P.G.是苄基(Bn)或对甲氧基苄基(PMB),R3按原始限定)和式1.10的化合物(其中P.G.是三异丙基甲硅烷基(TIPS),R3按原始限定)可以通过方案1,步骤a-h所示的方法制备。式1.0的化合物(其中Z是乙氧基(-OCH2CH3,OEt)或吡咯烷,P.G.是Bn或PMB)可以在极性非质子溶剂例如四氢呋喃(THF)中在约-20℃至约0℃的降低温度用有机金属亲核试剂例如环戊基溴化镁和还原剂例如硼氢化锂(LiBH4)的混合物进行处理,得到式1.1和1.2的化合物(其中R3如之前限定),如a中所示。式1.3的醇(其中P.G.是Bn)可以由式1.0的化合物(其中Z是OEt,P.G.是Bn)如下制备:在醚类溶剂例如乙醚(Et2O)中在约0℃的温度用氢化铝锂(LAH)进行处理,如b中所示。另外,可以如下将式1.0的化合物(其中Z是OEt,P.G.是Bn或PMB)转化为式1.4的醛:在卤化溶剂例如二氯甲烷(CH2Cl2)中用催化剂例如氯二(环辛烯)铱(I)二聚物(Ir2(coe)4Cl2)和还原剂例如二乙基硅烷(Et2SiH2)进行处理,如Cheng,C.;Brookhart,M.Angew.Chem.Int.Ed.2012,51,9422-9424中所述和如c中所示。式1.5和1.6的化合物(其中R3如之前限定)可以如下获得:在极性非质子溶剂如THF中在约-78℃至约23℃的降低温度用碳亲核试剂例如苯基溴化镁或(E)-丙-1-烯-1-基溴化镁处理式1.4的醛,如d中所述。可以如下将式1.5和1.6的化合物(其中R3如之前限定)的混合物氧化以得到式1.7的化合物(其中R3按原始限定):在溶剂如CH2Cl2中,在约0℃至约23℃的温度,用氧化剂例如戴斯-马丁高碘烷(DMP)进行处理,如e中所示。式1.8的化合物(其中R3如之前限定)可以如下制备:在醚类溶剂如Et2O中在约0℃至约23℃的温度,用还原剂例如硼氢化锌处理式1.7的化合物(其中R3如之前限定),所述硼氢化锌由氯化锌(II)(ZnCl2)和硼氢化钠(NaBH4)原位制备,如f中所述。式1.0的化合物(其中P.G.是TIPS)可以在卤化溶剂如CH2Cl2中在约-78℃至约0℃的温度用还原剂例如二异丁基氢化铝(DIBAL)进行处理,得到式1.9的醛,如g中所述。式1.10的化合物可以由式1.9的醛如下制备:在醚类溶剂如Et2O中在约-78℃至约0℃的温度,用亲核试剂例如(+)-Ipc2-烯丙基硼烷进行处理,如h中所示。
方案1
式2.3的化合物(其中R8按原始限定)可以通过方案2,步骤a-b所示的方法制备。如a中所述,式2.1的化合物(其中R8按原始限定)可以由式2.0的化合物(其中R8按原始限定)如下制备:在镍催化剂例如二(环辛二烯)镍(0)(Ni(cod)2)存在下,在约0℃至约23℃的温度在非质子溶剂如甲苯中,用脂族饱和烃基氧基硼烷例如频哪醇硼烷进行制备,如Ely,R.J.;Morken,J.P.J.Am.Chem.Soc.2010,132,2534-2535所述。式2.3的化合物(其中R8如之前限定)可以由式2.1的化合物(其中R8如之前限定)通过用苄基(Bn)或对甲氧基苄基(PMB)保护的源自乳酸酯的醛例如式2.2的化合物进行处理制备,如b中所示。
方案2
式3.2的化合物(其中R8按原始限定)可以通过方案3,步骤a-b所示的方法制备。式3.1的化合物(其中R8按原始限定)可以如下制备:在极性非质子溶剂如THF中在约-78℃至约23℃的温度,用脂族饱和烃基锂试剂例如仲丁基锂、然后用脂族饱和烃基氧基硼烷例如B-甲氧基二异松蒎烯基硼烷处理式3.0的化合物(其中R8按原始限定),如Brown,H.C.;Jadhav,P.K.;Bhat,K.S.J.Am.Chem.Soc.1988,110,1535-1538中所述且如a中所示。式3.2的化合物(其中R8如之前限定)可以由式3.1的化合物(其中R8如之前限定)如下制备:在约-78℃至约23℃的温度,用Lewis酸例如三氟化硼乙醚化物、然后用Bn或PMB保护的源自乳酸酯的醛例如式2.2的化合物进行处理,如b中所示。
方案3
式4.1、4.2、4.3、和4.4的化合物(其中R3按原始限定)可以使用方案4,步骤a-f所示的方法获得。式4.1的化合物(其中R3如之前限定,R4是酰基)可以由式4.0的化合物(其中R3如之前限定)如下制备:在碱例如三乙胺(TEA)和胺催化剂例如N,N-二甲基氨基吡啶(DMAP)存在下,在卤化溶剂如CH2Cl2中,用酰基卤化物例如异丁酰氯进行处理,如a中所示。式4.2的化合物(其中R3如之前限定,R4是芳基)可以如下制备:在催化剂例如乙酸铜(II)(Cu(OAc)2)存在下,在约50℃的升高温度,用有机金属物质例如二(乙酸-O)三苯基-铋(V)(Ph3Bi(OAc)2)处理式4.0的化合物(其中R3如之前限定)在溶剂如甲苯中的溶液,如b中所示。或者,式4.2的芳基化产物(其中R3如之前限定)可以如下制备:在极性非质子溶剂如N,N-二甲基甲酰胺(DMF)中在约50℃至约70℃的升高温度,用芳基氟化物例如1,3-二氟苯和醇盐碱例如叔丁醇钾(KOt-Bu)处理式4.0的化合物(其中R3如之前限定),如c中所示。式4.3的化合物(其中R3如之前限定,R4是脂族饱和烃基)可以由式4.0的化合物(其中R3如之前限定)如下制备:在极性非质子溶剂如DMF中在约50℃的升高温度,用碱例如KOt-Bu或氢化钠(NaH)和亲电试剂例如脂族饱和烃基卤化物如(溴甲基)环丙烷进行处理,如d中所示。式4.4的化合物(其中R3如之前限定,R4是烯基)可以由式4.0的化合物(其中R3如之前限定)如下制备:在极性非质子溶剂如DMF中在约50℃的升高温度,用碱例如KOt-Bu或NaH和烯丙基亲电试剂例如3-溴-2-甲基丙-1-烯进行处理,如e中所示。或者,式4.4的化合物(其中R3如之前限定,R4是烯基)可以由式4.0的化合物如下制备:在钯催化剂例如三(二亚苄基丙酮)-二钯(0)(Pd2(dba)3)和配体例如1,1′-双(二苯基膦基)二茂铁(dppf)存在下,在极性非质子溶剂如THF中在约65℃的升高温度,用对称或混合的碳酸烯丙基酯例如碳酸叔丁基环戊-2-烯-1-基酯进行处理,如f中所述。
方案4
式5.1的化合物(其中R3按原始限定但不是烯基)可以根据方案5所示的方法制备。式5.0的化合物(其中R3按原始限定但不是烯基)可以在碱金属碳酸盐碱例如碳酸钠(Na2CO3)存在下在混合溶剂体系例如二氧杂环己烷水溶液中在约80℃的升高温度用钯催化剂如四(三苯基膦)钯(0)(Pd(PPh3)4)和硼酸酯或硼酸例如苯基硼酸进行处理,得到式5.1的化合物(其中R3如之前限定),如a中所示。
方案5
式6.2、6.4、和6.5的化合物(其中Z是亚甲基(CH2)或氧(O),R4和R8按原始限定但不是烯基,R10是脂族饱和烃基)可以通过方案6,步骤a-f所示的方法获得。式6.1的化合物(其中Z是CH2或O,R4和R8按原始限定但不是烯基)可以由式6.0的化合物(其中Z是CH2或O,R4和R8按原始限定但不是烯基)通过标准硼氢化条件制备,即如下制备:在极性非质子溶剂如THF中在约23℃用硼烷试剂例如9-硼杂双环[3.3.1]壬烷(9-BBN)进行处理,并通过用氢氧化钠(NaOH)和过氧化氢(H2O2)进行处理将所得硼中间体氧化,如a中所示。式6.2的化合物(其中Z、R4、R8和R10如之前限定)可以如下制备:在碱例如N,N,N’,N’-四甲基萘-1,8-二胺(Proton)存在下在极性非质子溶剂如CH2Cl2中在约0℃至约23℃的温度,用亲电试剂例如三甲基氧鎓四氟硼酸盐(trimethyloxonium tetrafluoroborate)处理式6.1的化合物(其中Z、R4、和R8如之前限定),如b中所示。或者,式6.1的醇(其中Z、R4、和R8如之前限定)可以如下进一步官能化:在lewis酸例如三氟甲磺酸钪(III)(Sc(OTf)3)存在下,在非质子溶剂如CH2Cl2中在约0℃至约23℃的温度,用保护的氮丙啶例如氮丙啶-1,2-二甲酸(R)-2-苄基-1-叔丁基酯进行处理,如c中所示。式6.3的化合物(其中Z是CH2或O,R4和R8按原始限定但不是烯基)可以如下制备:使式6.0的化合物(其中Z、R4、和R8如之前限定)经受标准臭氧分解/还原条件,即在溶剂混合物例如例如CH2Cl2和甲醇(MeOH)中在约-78℃的温度用臭氧(O3)进行处理,然后添加硼氢化钠(NaBH4)和MeOH,如d中所示。式6.4的化合物(其中Z、R4、R8、和R10如之前限定)可以由式6.3的化合物(其中Z、R4、和R8如之前限定)如下制备:在非质子溶剂如CH2Cl2中在约0℃至约23℃的温度,用亲电试剂例如三甲基氧鎓四氟硼酸盐和碱例如Proton进行处理,如e中所示。式6.5的环丙基化合物(其中Z、R4、和R8如之前限定)可以如下制备:在二乙基锌(Et2Zn)存在下在约0℃至约23℃的温度,用二卤代甲烷试剂例如二碘甲烷处理式6.0的化合物(其中Z、R4、和R8如之前限定)的醚溶液,如f中所示。
方案6
式7.2的化合物(其中R4和R10按原始限定)可以根据方案7,步骤a-b所示的方法制备。可以使式7.0的化合物(其中R4按原始限定)经受方案6,步骤d中所述的臭氧分解条件,得到式7.1的化合物(其中R4按原始限定),如a中所示。式7.2的化合物(其中R4按原始限定,R10是脂族饱和烃基)可以由式7.1的化合物(其中R4如之前限定)如下制备:在极性非质子溶剂如DMF中在约0℃至约23℃的温度用碱例如NaH进行处理,并用亲电试剂例如4-甲基苯磺酸丙基酯将所得脂族饱和烃基氧基化物淬灭,如b中所示。另外,式7.2的化合物(其中R4按原始限定,R10是芳基)可以由式7.1的醇(其中R4如之前限定)使用方案4,步骤b中所述的芳基化条件制备,如c中所示。
方案7
式8.3的化合物(其中R3和R4按原始限定)可以根据方案8,步骤a-d所示的方法制备。式8.3的化合物(其中R3和R4如之前限定但不是烯基)可以如下制备:在氢气(H2)存在下在极性溶剂如乙酸乙酯(EtOAc)或MeOH中用催化剂例如钯碳(Pd/C)处理式8.0的化合物(其中R3和R4按原始限定),或者在极性溶剂如EtOH中用可替代的氢源例如环己烯处理式8.0的化合物(其中R3和R4按原始限定),如a中所示。另外,可以使式8.0的化合物(其中R3如之前限定,R4是芳基氯)经受改良的氢解条件,即在Pd/C和NEt3存在下使芳基氯化物的EtOH溶液暴露于H2,得到式8.3的化合物(其中R3和R4按原始限定,但R3不是烯基),如b中所示。式8.3的化合物(其中R3和R4按原始限定)可以如下获得:在溶剂混合物如CH2Cl2水溶液中,用氧化剂例如2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)处理式8.1的化合物(其中R3和R4按原始限定),如c中所述。式8.3的化合物(其中R3和R4按原始限定)也可以如下制备:在溶剂如THF中在约0℃至约23℃的温度,用氟化物源例如四-N-丁基氟化铵(TBAF)处理式8.2的化合物(其中R3和R4按原始限定),如d中所述。
方案8
式9.3的化合物(其中R3按原始限定但不是烯基)可以根据方案9,步骤a-c所示的方法制备。如a中所述,式9.0的化合物可以在极性非质子溶剂如THF中在约-10℃至约0℃的温度用还原剂例如LiBH4和碳亲核试剂例如格氏试剂如异丙基氯化镁进行处理,得到式9.1的化合物(其中R3按原始限定)。式9.2的化合物(其中R3按原始限定)可以由式9.1的化合物(其中R3如之前限定)如下制备:用碱例如KOt-Bu进行处理,和在极性非质子溶剂如DMF中用亲电试剂例如1-氯-3-氟苯将所得脂族饱和烃基氧基化物阴离子淬灭,如b中所示。式9.3的化合物(其中R3如之前限定)可以由式9.2的化合物(其中R3如之前限定)使用方案8,步骤b中所述的方法制备,如c中所示。
方案9
式10.2和10.3的化合物(其中R2和R3按原始限定)可以使用方案10,步骤a-d所述的方法制备。式9.3的化合物(其中R3按原始限定)可以用酸的水溶液例如1当量浓度(N)氯化氢(HCl)进行处理,得到式10.0的二醇(其中R3按原始限定),如a中所述。式10.1的化合物(其中R3按原始限定)可以由式10.0的化合物(其中R3如之前限定)如下制备:在卤化质子溶剂如CH2Cl2中在约23℃的温度,用氧化剂例如高碘酸钠(NaIO4)进行处理,如b中所示。式10.1的醛(其中R3如之前限定)可以在溶剂如MeOH中在约23℃的温度用还原剂例如NaBH4进行处理,得到式10.2的醇(其中R2和R12是氢,R3如之前限定),如c中所示。另外,式10.1的醛(其中R3如之前限定)可以在极性非质子溶剂如THF中在约-78℃的温度用碳亲核试剂例如格氏试剂如乙基溴化镁(EtMgBr)进行处理,得到式10.3的化合物(其中R2和R3按原始限定,R12是氢),如d中所述。
方案10
式11.2的化合物(其中R2、R3、和R12按原始限定)可以根据方案11,步骤a-c所示的方法制备。如a中所示,式9.3的缩醛(其中R3按原始限定)可以在混合溶剂体系中例如在乙腈(CH3CN)、四氯化碳(CCl4)、和水(H2O)中用氧化剂例如原高碘酸进行处理,然后用第二氧化剂例如三氯化钌(RuCl3)进行处理,得到式11.0的羧酸(其中R3按原始限定)。式11.0的化合物(其中R3如之前限定)可以在溶剂混合物中例如在THF、苯、和MeOH中用三甲基甲硅烷基重氮甲烷进行处理,得到式11.1的酯(其中R3按原始限定),如b中所示。式11.2的化合物(其中R2、R3、和R12如之前限定)可以由式11.1的酯(其中R3如之前限定)如下制备:在约0℃至约23℃的温度,在醚溶剂的混合物中例如在THF和Et2O中用碳亲核试剂例如格氏试剂如甲基溴化镁(MeMgBr)进行处理,如c中所示。
方案11
式12.2的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定)可以根据方案12所示的方法制备。式12.0的醇(其中R2、R3、R4、和R12按原始限定)可以在卤化溶剂如CH2Cl2中用式12.1的化合物(其中R1和R11按原始限定)、偶联试剂例如3-(乙基亚氨基亚甲基氨基)-N,N-二甲基丙-1-胺氢氯化物(EDC)或聚合物负载的碳二亚胺(PS-CDI)、和催化剂例如DMAP进行处理,得到式12.2的化合物(其中R1、R2、R3、R4、R11、和R12如之前限定),如a中所示。
方案12
式13.3的化合物(其中R1、R4、和R11按原始限定,R8是脂族饱和烃基)可以根据方案13,步骤a-c所示的方法制备。如a中所述,式13.1的化合物(其中R1、R4、和R11按原始限定)可以如下制备:在非质子溶剂如CH3CN中在约23℃,用二碳酸二叔丁基酯(BOC2O)和DMAP处理式13.0的化合物(其中R1、R4、和R11按原始限定)。式13.2的化合物(其中R1、R4、和R11按原始限定)可以由式13.1的化合物(其中R1、R4、和R11如之前限定)使用方案6,步骤d中所述的臭氧分解条件制备,如b中所示。式13.3的化合物(其中R1、R4、R8、和R11如之前限定)可以由式13.2的化合物(其中R1、R4、和R11如之前限定)使用方案6,步骤b中所述的方法制备,如c中所示。
方案13
式14.7的化合物(其中R1、R2、R3、R4、R6、R11、和R12按原始限定)可以根据方案14,步骤a-e所示的方法制备。式14.0的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定但不是烯基)可以在卤化质子溶剂如CH2Cl2中用酸例如HCl在二氧杂环己烷中的4N溶液进行处理,得到式14.2的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定但不是烯基),如a中所示。式14.3的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定)可以如下制备:在卤化质子溶剂如CH2Cl2中,用酸例如2,2,2-三氟乙酸处理式14.0的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定),如b中所示。式14.4的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定)可以如下制备:在卤化质子溶剂如CH2Cl2中,用试剂例如三氟甲磺酸三甲基甲硅烷基酯(TMSOTf)和胺碱例如2,6-二甲基吡啶处理式14.0的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定),如c中所示。式14.5的化合物(其中R1、R2、R3、R4、R11、和R12如之前限定)可以如下制备:在极性非质子溶剂如THF中,用胺碱例如吗啉处理式14.1的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定),如d中所示。式14.2、14.3、14.4、和14.5的化合物(其中R1、R2、R3、R4、R11、和R12按原始限定)可以在碱例如二异丙基乙基胺和肽偶联剂例如苯并三唑-1-基-氧基三吡咯烷六氟磷酸盐(PyBOP)或O-(7-氮杂苯并三唑-1-基)-N,N,N′,N′-四甲基六氟磷酸盐(HATU)存在下在卤化溶剂如CH2Cl2中用式14.6的化合物(其中R6按原始限定)进行处理,得到式14.7的化合物(其中R1、R2、R3、R4、R6、R11、和R12如之前限定),如e中所示。
方案14
式15.1的化合物(其中R1、R2、R3、R6、R11、和R12按原始限定但不是烯基,R8按原始限定但不是烯基或氯)可以根据方案15所示的方法制备。可以使式15.0的化合物(其中R1、R2、R3、R6、R8、R11、和R12按原始限定)经受方案8,步骤b中所述的氢化条件,得到式15.1的化合物(其中R1、R2、R3、R6、R8、R11、和R12如上文限定),如a中所述。
方案15
式16.1的化合物(其中R1、R2、R3、R4、R6、R7、R11、和R12按原始限定)可以根据方案16所示的方法制备。式16.0的化合物(其中R1、R2、R3、R4、R6、R11、和R12如之前限定)可以在使用或不使用试剂例如碘化钠(NaI)和碱金属碳酸盐碱例如Na2CO3或碳酸钾(K2CO3)的情况下在溶剂如丙酮中用适当的脂族饱和烃基卤化物进行处理,或者在胺碱例如吡啶、NEt3、DMAP、或其混合物存在下在非质子溶剂例如CH2Cl2中用酰基卤化物进行处理,得到式16.1的化合物(其中R1、R2、R3、R4、R6、R7、R11、和R12如之前限定),如a中所示。
方案16
实施例
实施例1A:制备(2S,3R)-2-(苄氧基)-4-乙基己-3-醇和(2S,3S)-2-(苄氧基)-4-乙基己-3-醇。
历时约1小时(h)时间段经注射泵添加向戊-3-基溴化镁(77.0毫升(mL),154毫摩尔(mmol))和硼氢化锂(LiBH4;49.9mL,100mmol,2摩尔浓度(M),在THF中)在THF(400mL)的-5℃溶液中逐滴添加纯的(S)-2-(苄氧基)丙酸乙酯(16.0克(g),77.0mmol),其添加速率可保持内部温度低于-3℃。历经一夜将反应容器缓慢升温至室温,通过历时30分钟(min)的时间段将该混合物添加到水(H2O,300mL)中而将反应混合物淬灭。将混合物用乙醚(Et2O;300mL)稀释,将各相分离,将水(aq.)相用Et2O(2 x 100mL)萃取。将合并的有机相用饱和(sat.)氯化钠水溶液(NaCl,盐水;300mL)洗涤,用硫酸镁(MgSO4)干燥,过滤,并浓缩。将所得油状物通过快速柱色谱纯化(硅胶(SiO2),0→15%乙酸乙酯(EtOAc)在己烷中),得到作为无色油状物的标题化合物(分别为9.61g,53%和3.46g,19%):
主要产物:IR(薄膜)3471,3031,2962,2932,2874,1454,1382cm-1;1H NMR(400MHz,CDCl3)δ7.38-7.26(m,5H),4.60(d,J=11.8Hz,1H),4.51(d,J=11.8Hz,1H),3.68(ddd,J=7.4,3.6,2.7Hz,1H),3.63(qd,J=6.2,3.7Hz,1H),2.05(d,J=2.8Hz,1H),1.65(dq,J=9.9,7.4Hz,1H),1.44-1.34(m,2H),1.36-1.18(m,2H),1.18(d,J=6.2Hz,3H),0.88(t,J=7.3Hz,3H),0.84(t,J=7.4Hz,3H);13C NMR(101MHz,CDCl3)δ138.53,128.41,127.63,127.60,75.65,73.56,70.50,41.34,20.59,20.51,13.13,10.44,10.29;
次要产物:IR(薄膜)3472,3031,2961,2932,2874,1497,1454,1376cm-1;1H NMR(400MHz,CDCl3)δ7.39-7.32(m,4H),7.32-7.26(m,1H),4.68(d,J=11.3Hz,1H),4.44(d,J=11.4Hz,1H),3.66-3.54(m,1H),3.43(dt,J=6.8,3.8Hz,1H),2.43(dd,J=4.0,0.8Hz,1H),1.54-1.36(m,3H),1.36-1.23(m,2H),1.19(d,J=6.1Hz,3H),0.90(t,J=7.4Hz,3H),0.89(t,J=7.3Hz,3H);13C NMR(101MHz,CDCl3)δ138.40,128.46,127.79,127.73,76.67,76.07,70.99,42.65,22.73,20.79,15.78,11.98,11.65。
实施例1B,步骤1:制备(S)-2-((4-甲氧基苄基)氧基)丙醛。
历时10min时间段向(S)-2-((4-甲氧基苄基)氧基)丙酸乙酯(5.00g,21.0mmol)在CH2Cl2(30mL)的0℃溶液中添加氯二(环辛烯)铱(I)二聚物(Ir2Cl2(coe)4;94.0毫克(mg),0.105mmol),然后添加二乙基硅烷(Et2SiH2;4.08mL,31.5mmol)。将混合物在0℃搅拌30min,升温至室温并搅拌3h,冷却至0℃,并通过添加1当量浓度(N)氯化氢水溶液(HCl;12mL)将其淬灭。将所得溶液升温至室温并搅拌15min。将各相分离,将水相用CH2Cl2(3 x 30mL)萃取。将合并的有机相用盐水洗涤,用硫酸钠(Na2SO4)干燥,过滤,蒸发,并通过快速柱色谱纯化(SiO2,2→50%丙酮在己烷中),得到作为黄色油状物的标题化合物(4.27g,100%):IR(薄膜)2934,2837,2865,1731,1512cm-1;1H NMR(300MHz,CDCl3)δ9.64(d,J=1.9Hz,1H),7.35-7.21(m,2H),6.95-6.79(m,2H),4.63-4.40(m,2H),3.94-3.76(m,1H),3.81(s,3H),1.31(d,J=6.9Hz,3H);13C NMR(101MHz,CDCl3)δ203.58,159.54,129.65,129.37,113.98,79.14,71.75,55.30,15.34。
实施例1B,步骤2:制备(1S,2S)-2-((4-甲氧基苄基)氧基)-1-苯基丙-1-醇。
向(S)-2-((4-甲氧基苄基)氧基)丙醛(3.38g,17.4mmol)在Et2O(58mL)的-78℃溶液中逐滴添加苯基溴化镁(34.8mL,34.8mmol,1M在THF中),将反应混合物升温至室温,搅拌过夜,并通过添加氯化铵饱和水溶液(NH4Cl)将其淬灭。将混合物在H2O和EtOAc之间分配,将各相分离,将水相用EtOAc萃取(2x)。将合并的有机相用盐水洗涤,用Na2SO4干燥,过滤,蒸发,并通过快速柱色谱纯化(SiO2,2→50%丙酮在己烷中),得到作为黄色油状物的标题化合物(3.29g,66%),其为非对映异构体的不可分离的混合物(d.r.为3∶1的SS∶RS):1H NMR(400MHz,CDCl3;主要产物)δ7.37-7.25(m,7H),6.89(d,J=8.6Hz,2H),4.62(d,J=11.0Hz,1H),4.44(dd,J=7.8,2.1Hz,1H),4.41(d,J=11.0Hz,1H),3.82(s,3H),3.60(dq,J=7.8,6.2Hz,1H),3.21(d,J=2.1Hz,1H),1.05(d,J=6.2Hz,3H);13C NMR(101MHz,CDCl3)δ159.34,140.56,130.21,129.46,128.31,127.25,126.31,113.93,79.66,78.32,70.92,55.30,15.56;ESIMS m/z 295(([M+Na]+))。
实施例1B,步骤3:制备(S,E)-2-(苄氧基)己-4-烯-3-酮。
向(2S)-2-(苄氧基)己-4-烯-3-醇(1.3g,6.30mmol)和碳酸氢钠(NaHCO3;0.582g,6.93mmol)在CH2Cl2(25.2mL)的0℃溶液中添加戴斯-马丁高碘烷(DMP;2.94g,6.93mmol),将反应混合物从冷浴中取出,在室温搅拌6h,并通过添加硫代硫酸钠饱和水溶液(Na2S2O3;10mL)将其淬灭。将混合物用CH2Cl2(10mL)稀释,将两相溶液剧烈搅拌15min,用H2O(10mL)稀释,将各相分离。将水相用CH2Cl2(2 x 15mL)萃取,将合并的有机相依次用NaHCO3饱和水溶液(10mL)、H2O(20mL)、和盐水(20mL)洗涤,用Na2SO4干燥,过滤,并浓缩。将粗制残余物通过快速柱色谱纯化(SiO2,0→50%EtOAc在己烷中),得到标题化合物(480mg,37%)和(S,Z)-2-((4-甲氧基苄基)氧基)己-4-烯-3-酮,将后者溶解于CH2Cl2(5mL)并将其在DABCO(10mg)存在下搅拌18h,得到另外的标题化合物(400mg,31%):1H NMR(400MHz,CDCl3)δ7.40-7.26(m,5H),7.08(dq,J=15.6,6.9Hz,1H),6.55(dq,J=15.6,1.7Hz,1H),4.57(d,J=11.7Hz,1H),4.43(d,J=11.7Hz,1H),4.05(q,J=6.9Hz,1H),1.93(dd,J=6.9,1.7Hz,3H),1.36(d,J=6.9Hz,3H);13C NMR(101MHz,CDCl3)δ201.11,144.70,137.66,128.45,127.84,126.07,80.00,71.76,18.56,18.00;ESIMS m/z 205(([M+H]+))。
实施例1B,步骤4:制备(2S,3R,E)-2-(苄氧基)己-4-烯-3-醇。
向NaBH4(445mg,11.8mmol)在Et2O(15.7mL)的0℃溶液中添加氯化锌(II)(ZnCl2;5.90mL,5.87mmol,1M在Et2O中),将混合物从冷浴中取出并将其在室温搅拌18h。将反应混合物冷却至0℃,用(S,E)-2-(苄氧基)己-4-烯-3-酮(800mg,3.92mmol)在Et2O(2mL)中的溶液逐滴处理,并搅拌2h。将反应混合物升温至室温,在室温搅拌3h,用THF(5mL)稀释,并继续搅拌另外1h,然后通过小心添加NH4Cl饱和水溶液(25mL)将其淬灭。将各相分离,将水相用Et2O(3 x 20mL)萃取。将合并的有机相用盐水(10mL)洗涤,用Na2SO4干燥,过滤,蒸发,将粗制残余物通过快速柱色谱纯化(SiO2,0→35%EtOAc在己烷中),得到作为无色油状物的标题化合物(620mg,77%):1H NMR(400MHz,CDCl3)δ7.38-7.24(m,5H),5.80-5.66(m,1H),5.55-5.43(m,1H),4.63(d,J=11.8Hz,1H),4.53(d,J=11.8Hz,1H),4.20-4.12(m,1H),3.57(qd,J=6.4,3.4Hz,1H),2.28-2.22(m,1H),1.75-1.68(m,3H),1.14(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ138.54,129.43,128.68,128.42,127.64,77.76,74.62,70.86,17.91,14.20;ESIMS m/z 229(([M+Na]+))。
实施例1C,步骤1:制备(S)-2-((三异丙基甲硅烷基)氧基)丙醛。
历时4h向(S)-2-((三异丙基甲硅烷基)氧基)丙酸乙酯(20.5g,74.7mmol)在CH2Cl2(373mL)的-78℃溶液中添加二异丙基氢化铝的溶液(DIBAL;149mL,149mmol,1M在CH2Cl2中),将反应混合物在-78℃搅拌另外30min,用EtOAc(75mL)淬灭,并升温至0℃。将非均相混合物用酒石酸钠水溶液(~200mL)处理,将混合物升温至室温并剧烈搅拌过夜。将各相分离,将水相用CH2Cl2(2 x 150mL)萃取。将合并的有机相用Na2SO4干燥,过滤,并浓缩成油状物,将其通过快速柱色谱纯化(SiO2,0→10%EtOAc在己烷中),得到作为透明无色油状物的标题化合物(12.64g,70%):1H NMR(400MHz,CDCl3)δ9.66(d,J=1.7Hz,1H),4.18(qd,J=6.8,1.7Hz,1H),1.31(d,J=6.8Hz,3H),1.07(td,J=5.6,5.0,3.2Hz,21H);13C NMR(101MHz,CDCl3)δ204.58,73.82,18.95,17.89,12.14;EIMS m/z 187[M-i-Pr]+。
实施例1C,步骤2:制备(2S,3R)-2-((三异丙基甲硅烷基)氧基)己-5-烯-3-醇。
历时1.5h向(+)-Ipc2-烯丙基硼烷(25.0mL,25.0mmol,1M在戊烷中)在Et2O(100mL)的-78℃溶液中添加(S)-2-((三异丙基甲硅烷基)氧基)丙醛(4.61g,20.0mmol)在Et2O(60mL)的溶液,将反应混合物在-78℃搅拌另外1.5h,用MeOH(50mL)处理,并搅拌5min。将混合物用pH 7缓冲液(70mL)处理,升温至0℃,并用30%H2O2水溶液(60mL)处理。将反应混合物在0℃搅拌2.5h,使其缓慢升温至室温,并搅拌30h。将各相分离,将水相用Et2O(3 x 100mL)萃取。将合并的有机相用MgSO4干燥,过滤,并浓缩成透明油状物,将其通过快速柱色谱纯化(SiO2,0→15%EtOAc在己烷中),得到作为透明的微玫瑰色油状物的标题化合物(5.00g,87%):IR(无底物)3480,2943,2866,1463,1067,881cm-1;1H NMR(400MHz,CDCl3)δ5.85(ddt,J=17.2,10.2,7.0Hz,1H),5.22-4.97(m,2H),3.93(qd,J=6.2,3.3Hz,1H),3.70(ddt,J=8.3,5.7,2.9Hz,1H),2.34(d,J=2.6Hz,1H),2.30-2.09(m,2H),1.14(d,J=6.3Hz,3H),1.12-1.03(m,21H);HRMS-ESI(m/z)([M+H]+),对于C15H33O2Si,计算值为274.2270;实测值为274.2274。
实施例1D:制备(S)-2-(苄氧基)丙-1-醇。
历时10min的时间段向LAH(48.0ml,24.0mmol,0.5M在Et2O中)的0℃溶液中逐滴添加(S)-2-(苄氧基)丙酸乙酯(5.00g,24.0mmol),将反应混合物在0℃搅拌3h,通过依次添加H2O(900μL)、1N NaOH(900μL)、和水(2.7mL)将其淬灭。将所得浆液在室温搅拌10min,用Na2SO4处理,将混合物过滤通过将滤液浓缩,得到作为无色油状物的标题化合物(4.00g,24.1mmol,100%):1H NMR(400MHz,CDCl3)δ7.41-7.26(m,5H),4.65(d,J=11.6Hz,1H),4.48(d,J=11.6Hz,1H),3.74-3.56(m,2H),3.49(ddd,J=11.5,7.0,4.6Hz,1H),2.21(dd,J=7.9,4.6Hz,1H),1.17(d,J=6.2Hz,3H);13C NMR(101MHz,CDCl3)δ138.46,128.48,127.75,127.73,75.57,70.82,66.36,15.89;EIMS m/z 166。
实施例1E:制备(1S,2S)-2-((4-甲氧基苄基)氧基)-1-(噻吩-2-基)丙-1-醇和(1R,2S)-2-((4-甲氧基苄基)氧基)-1-(噻吩-2-基)丙-1-醇。
历时约1h的时间段经注射泵添加向噻吩-2-基锂(4.00mL,4.00mmol,1M在THF中)和硼氢化锂(LiBH4;1.30mL,2.60mmol,2M在THF中)在THF(10mL)的-10℃溶液中逐滴添加纯的(S)-2-((4-甲氧基苄基)氧基)-1-(吡咯烷-1-基)丙-1-酮(0.527g,2.00mmol)(对于制备参见:Pellicena,M.;Solsona,J.G.;Romea,P.;Urpi,F.Tetrahedron 2012,68,10338.),其添加速率可保持内部温度低于-5℃。将反应容器经历一夜缓慢升温至室温,通过添加NH4Cl饱和水溶液将反应混合物淬灭。将水相用Et2O萃取(3x)。将合并的有机相用盐水洗涤,用Na2SO4干燥,过滤,蒸发,并通过快速柱色谱纯化(SiO2,2→10%丙酮在己烷中),得到作为无色油状物的标题化合物(分别为0.231g,41%和0.175g,31%):
主要产物:1H NMR(300MHz,CDCl3)δ7.32-7.21(m,3H),7.05-6.93(m,2H),6.94-6.83(m,2H),5.03(t,J=4.2Hz,1H),4.61(d,J=11.4Hz,1H),4.48(d,J=11.3Hz,1H),3.81(s,3H),3.88-3.73(m,1H),2.59(d,J=4.4Hz,1H),1.13(d,J=6.3Hz,3H);ESIMS m/z 579([2M+Na]+)。
次要产物:1H NMR(300MHz,CDCl3)δ7.34-7.22(m,3H),7.06-6.92(m,2H),6.95-6.84(m,2H),4.73(dd,J=7.3,2.7Hz,1H),4.63(d,J=10.9Hz,1H),4.44(d,J=11.0Hz,1H),3.82(s,3H),3.67(dq,J=7.3,6.2Hz,1H),3.29(d,J=2.8Hz,1H),1.14(d,J=6.1Hz,3H);ESIMS m/z 579([2M+Na]+)。
实施例2:制备(2S,3R,4S)-4-苄基-2-(苄氧基)己-5-烯-3-醇。
在惰性气氛(氮气(N2)手套袋)下向圆底烧瓶中添加二(环辛二烯)镍(0)(Ni(cod)2;0.168g,0.609mmol)和三环己基膦(P(C6H11)3;0.213g,0.761mmol),将烧瓶封上盖子并从袋中取出。将混合物用甲苯(22mL)稀释,在室温添加4,4,5,5-四甲基-1,3,2-二氧杂硼戊烷(6.63mL,45.7mmol)。将反应混合物在冰浴中冷却至0℃,并历时10min的时间段用纯的(E)-丁-1,3-二烯-1-基苯(4.76g,36.5mmol)逐滴处理。将混合物从冰浴中取出并在室温搅拌2h,将其在干冰/丙酮浴中冷却至-78℃,并用(S)-2-(苄氧基)丙醛(5.00g,30.5mmol)然后用BF3·OEt2(0.376mL,3.05mmol)进行处理。将反应混合物经历一夜缓慢升温至室温,通过用MeOH(5mL)处理而将其淬灭。搅拌30min之后,将反应混合物浓缩并通过快速柱色谱纯化(SiO2,0→50%EtOAc在己烷中),得到作为无色油状物的标题化合物(8.95g,99%):1HNMR(400MHz,CDCl3)δ7.39-7.30(m,3H),7.32-7.25(m,1H),7.25-7.21(m,2H),7.20-7.11(m,4H),5.45(ddd,J=17.2,10.3,9.5Hz,1H),4.93(dd,J=10.3,1.8Hz,1H),4.79(ddd,J=17.2,1.9,0.7Hz,1H),4.55(d,J=11.7Hz,1H),4.46(d,J=11.7Hz,1H),3.76(ddd,J=9.2,3.2,2.2Hz,1H),3.56(qd,J=6.3,3.1Hz,1H),3.19(dd,J=13.3,3.5Hz,1H),2.58(dd,J=13.4,9.3Hz,1H),2.39(dt,J=9.2,3.4Hz,1H),2.37(d,J=2.3Hz,1H),1.17(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ139.92,138.48,137.37,129.81,128.46,127.94,127.70,127.66,125.76,117.21,76.22,73.78,70.56,48.44,37.63,12.21;ESIMS m/z 319(([M+Na]+))。
实施例3:制备(2S,3S,4S)-2-(苄氧基)-4-苯氧基己-5-烯-3-醇。
向3-丙氧基丙-1-烯(5.77g,57.6mmol)在THF(87mL)的-78℃溶液中缓慢添加仲丁基锂的溶液(s-BuLi;37.4mL,52.4mmol,1.4M在环己烷中),将所得溶液在-78℃搅拌40min,用甲氧基二((2S,3R)-2,6,6-三甲基双环[3.1.1]庚-3-基)硼烷(16.57g,52.4mmol)处理,并在-78℃搅拌另外2.5h。将反应混合物升温至0℃,并在0℃通过缓慢添加1N氢氧化钠水溶液(NaOH;63mL)然后添加30%过氧化氢水溶液(H2O2;21mL)将其淬灭。将所得混合物升温至室温并搅拌过夜。将各相分离,将水相用Et2O萃取(3x),将合并的有机萃取物用H2O和盐水洗涤,用Na2SO4干燥,过滤,并蒸发。将所得粗制油状物通过克氏蒸馏纯化(温度(T)=60℃,0.4-0.6毫米(mm)Hg),得到作为微黄色油状物的标题化合物(10.6g,77%):1H NMR(400MHz,CDCl3)δ7.37-7.33(m,4H),7.32-7.26(m,1H),5.76(ddd,J=17.2,10.4,7.5Hz,1H),5.28(ddd,J=8.9,1.8,0.9Hz,1H),5.28-5.22(m,1H),4.61(d,J=11.6Hz,1H),4.48(d,J=11.7Hz,1H),3.83(ddt,J=7.5,4.5,0.9Hz,1H),3.58(p,J=6.1Hz,1H),3.53-3.43(m,2H),3.18(dt,J=9.1,6.6Hz,1H),2.42(d,J=5.8Hz,1H),1.62-1.45(m,2H),1.27(d,J=6.2Hz,3H),0.90(t,J=7.4Hz,3H);13C NMR(101MHz,CDCl3)δ138.59,135.88,128.34,127.77,127.54,118.33,80.16,76.18,74.70,70.69,70.47,23.01,15.25,10.70;HRMS-ESI(m/z)([M+H]+),对于C16H25O3,计算值为265.1798;实测值为265.1793。
实施例4A:制备异丁酸(S)-2-(苄氧基)丙基酯。
向(S)-2-(苄氧基)丙-1-醇(500mg,3.01mmol)在无水CH2Cl2(10mL)的溶液中添加三乙胺(NEt3;839微升(μL),6.02mmol)、DMAP(36.7mg,0.301mmol)、和异丁酰氯(473μL,4.51mmol),将所得溶液在室温搅拌过夜。将反应混合物倒入1N HCl水溶液(20mL)中,将各相分离,将水相用CH2Cl2(2 x 20mL)萃取。将有机萃取物合并,用Na2SO4干燥,过滤,并蒸发,得到黄色油状物,将其通过快速柱色谱纯化(SiO2,0→20%丙酮在己烷中),得到作为透明无色油状物的标题化合物(687mg,97%):1H NMR(400MHz,CDCl3)δ7.37-7.26(m,5H),4.61(d,J=11.9Hz,1H),4.58(d,J=11.9Hz,1H),4.18-4.04(m,2H),3.76(pd,J=6.3,4.6Hz,1H),2.58(p,J=7.0Hz,1H),1.22(d,J=6.3Hz,3H),1.19(d,J=2.3Hz,3H),1.17(d,J=2.3Hz,3H);13C NMR(101MHz,CDCl3)δ176.98,138.51,128.37,127.60,127.58,72.71,71.04,67.16,34.00,19.01,18.99,16.99;ESIMS m/z 237(([M+H]+))。
实施例4B:制备1-((2S,3R,4S)-4-(苄氧基)-3-苯氧基-2-乙烯基戊基)-4-氟苯。
向(2S,3R,4S)-2-(苄氧基)-4-(4-氟苄基)己-5-烯-3-醇(3g,9.54mmol)在无水甲苯(48mL)的溶液中添加N-环己基-N-甲基环己胺(3.04mL,14.3mmol)、Ph3Bi(OAc)2(7.73g,14.3mmol)、和乙酸铜(Cu(OAc)2;0.347g,1.91mmol)。将所得蓝色悬浮液加热至50℃并在50℃搅拌15h,将其冷却至室温,过滤通过短柱,并蒸发。将所得粗制物质通过快速柱色谱纯化(SiO2,1→5%EtOAc在己烷中),得到作为透明无色油状物的标题化合物(2.77g,74%):1H NMR(400MHz,CDCl3)δ7.38-7.18(m,7H),7.09-6.99(m,2H),6.996.84(m,5H),5.62(dt,J=17.2,9.7Hz,1H),4.96(dd,J=10.3,1.7Hz,1H),4.83(d,J=17.2Hz,1H),4.61(d,J=11.6Hz,1H),4.44(d,J=11.6Hz,1H),4.32(t,J=5.5Hz,1H),3.82(p,J=6.1Hz,1H),3.09(dd,J=13.5,4.1Hz,1H),2.71(dt,J=9.7,5.0Hz,1H),2.57(dd,J=13.3,9.8Hz,1H),1.27(d,J=6.2Hz,3H);13C NMR(151MHz,CDCl3)δ162.06,160.45,159.51,138.48,138.05,135.87,135.85,130.84,130.79,129.44,128.35,127.67,127.55,120.92,117.28,116.31,114.82,114.68,82.38,75.70,70.67,48.55,35.96,15.11;ESIMS m/z 413(([M+Na]+))。
实施例4C:制备1-((1R,2S)-2-(苄氧基)-1-环戊基丙氧基)-3-氯苯。
在室温向叔丁醇钾(KOt-Bu;314mg,2.80mmol)在无水N,N-二甲基甲酰胺(DMF;2mL)的悬浮液中添加(1R,2S)-2-(苄氧基)-1-环戊基丙-1-醇(469mg,2.00mmol),将所得橙色溶液搅拌5min,用1-氯-3-氟苯(643μL,6.00mmol)处理,将其加热至60℃并在60℃搅拌过夜。将冷却的反应混合物用冰醋酸(HOAc;300μL)淬灭,用己烷(2mL)稀释,将所得悬浮液通过快速柱色谱纯化(SiO2,2→8%丙酮在己烷中),得到作为无色油状物的标题化合物(637mg,92%):IR(薄膜)3065,2949,2866,1590,1474,1452cm-1;1H NMR(500MHz,CDCl3)δ7.35-7.30(m,2H),7.29-7.26(m,3H),7.14(t,J=8.1Hz,1H),7.05(t,J=2.2Hz,1H),6.88(dd,J=8.2,2.1Hz,2H),4.61(d,J=11.7Hz,1H),4.49(d,J=11.8Hz,1H),4.23(dd,J=7.4,3.7Hz,1H),3.70(qd,J=6.3,3.7Hz,1H),2.30-2.12(m,1H),1.851.74(m,1H),1.71-1.64(m,1H),1.66-1.46(m,4H),1.45-1.35(m,1H),1.25(d,J=6.3Hz,3H),1.23-1.15(m,1H);13C NMR(126MHz,CDCl3)δ160.99,138.48,134.62,130.03,128.33,127.51,127.48,120.72,116.88,114.73,85.07,76.56,70.85,42.16,29.40,28.98,25.46,25.12,14.78。
实施例4D:制备4-((1R,2S)-2-(苄氧基)-1-(环丙基甲氧基)-丙基)-1,1′-联苯。
向(1R,2S)-1-([1,1′-联苯]-4-基)-2-(苄氧基)丙-1-醇(272mg,0.854mmol)在无水DMF(2.8mL)的0℃溶液中添加氢化钠(NaH;59.8mg,1.50mmol,60wt%在矿物油中),将反应混合物在0℃搅拌15min。将混合物从冰浴中取出,搅拌另外15min,冷却回0℃,并用(溴甲基)环丙烷(84μL,0.854mmol)处理。在10min之后,将反应容器从冰浴中取出,将混合物升温至室温并在室温搅拌过夜。通过添加H2O然后搅拌10min而将反应混合物小心淬灭,将各相分离。将水相用Et2O萃取(3x),将合并的有机相用Na2SO4干燥,过滤,并浓缩。将所得油状物通过快速柱色谱纯化(SiO2,0→10%丙酮在己烷中),得到作为无色油状物的标题化合物(251mg,79%):1H NMR(400MHz,CDCl3)δ7.64-7.60(m,2H),7.57(d,J=8.2Hz,2H),7.48-7.32(m,5H),7.24-7.19(m,3H),7.10-7.06(m,2H),4.46(d,J=11.9Hz,1H),4.30(d,J=11.9Hz,1H),4.27(d,J=6.4Hz,1H),3.64(p,J=6.2Hz,1H),3.28-3.20(m,2H),1.32(d,J=6.2Hz,3H),1.12-1.01(m,1H),0.56-0.45(m,2H),0.22-0.10(m,2H);13C NMR(101MHz,CDCl3)δ141.03,140.33,139.54,138.60,128.75,128.18,128.14,127.67,127.30,127.18,127.06,126.73,84.36,78.56,73.75,71.47,16.71,10.74,3.18,2.83;ESIMS m/z 395(([M+Na]+))。
实施例4E:制备(S)-(((1-(叔丁氧基)丙-2-基)氧基)甲基)苯。
在室温向(S)-2-(苄氧基)丙-1-醇(300mg,1.80mmol)在无水CH2Cl2(9.0mL)的溶液中添加二碳酸二叔丁基酯(Boc2O;985mg,4.51mmol)和三氟甲磺酸钪(Sc(OTf)3;89mg,0.180mmol),将所得溶液在室温搅拌20h。将混合物用另外的Boc2O(400mg)处理,将混合物加热至40℃并在40℃搅拌4h。将反应混合物冷却至室温,浓缩,将残余物通过快速柱色谱纯化(SiO2,2→12%丙酮在己烷中),得到作为无色油状物的标题化合物(223mg,56%):1H NMR(400MHz,CDCl3)δ7.40-7.29(m,4H),7.29-7.23(m,1H),4.63(s,2H),3.64(h,J=6.2Hz,1H),3.48(dd,J=9.2,5.7Hz,1H),3.27(dd,J=9.2,5.6Hz,1H),1.23-1.16(m,12H);13C NMR(126MHz,CDCl3)δ139.13,128.26,127.61,127.33,74.56,72.84,71.21,66.08,27.52,17.70;ESIMS m/z 245(([M+Na]+))。
实施例4F:制备((((1R,2S)-1-环戊基-1-((2-甲基烯丙基)氧基)丙-2-基)氧基)甲基)苯。
向KOt-Bu(314mg,2.80mmol)在无水DMF(2mL)的悬浮液中添加(1R,2S)-2-(苄氧基)-1-环戊基丙-1-醇(469mg,2.00mmol)。将所得橙色溶液在室温搅拌5min,用3-溴-2-甲基丙-1-烯(605μL,6.00mmol)处理,将其升温至60℃并在60℃搅拌过夜。将冷却的反应混合物用冰HOAc(300μL)淬灭,用己烷(2mL)稀释,将所得悬浮液通过快速柱色谱纯化(SiO2,2→8%丙酮在己烷中),得到作为无色油状物的标题化合物(476mg,83%):IR(薄膜)3066,2947,2865,1726,1656,1452cm-1;1H NMR(500MHz,CDCl3)δ7.34(d,J=4.3Hz,4H),7.31-7.23(m,1H),4.98(dt,J=2.3,1.2Hz,1H),4.85-4.78(m,1H),4.58(d,J=11.9Hz,1H),4.52(d,J=12.0Hz,1H),4.23(d,J=12.0Hz,1H),3.96(d,J=12.0Hz,1H),3.58(qd,J=6.4,2.7Hz,1H),3.32(dd,J=8.1,2.6Hz,1H),2.01-1.88(m,1H),1.88-1.79(m,1H),1.76(d,J=1.3Hz,3H),1.66-1.57(m,3H),1.54-1.45(m,2H),1.44-1.35(m,1H),1.22(d,J=6.3Hz,3H),1.20-1.12(m,1H);13C NMR(126MHz,CDCl3)δ143.21,139.04,128.29,127.38,127.33,111.68,85.41,77.83,76.21,70.61,42.49,29.89,29.64,25.44,25.21,19.90,14.25。
实施例4G:制备((1R,2S)-2-(苄氧基)-1-甲氧基丙基)金刚烷。
向(1R,2S)-1-(金刚烷-1-基)-2-(苄氧基)丙-1-醇(0.550g,1.831mmol)在CH2Cl2(7.32ml)的0℃溶液中添加Proton (0.785g,3.66mmol)和三甲基氧鎓四氟硼酸盐(0.406g,2.75mmol),将反应混合物升温至室温并搅拌6h。添加另外的同等量的Proton和三甲基氧鎓四氟硼酸盐两者,将混合物在室温搅拌过夜。将反应混合物用NaHCO3饱和溶液淬灭,将各相分离,将产物用CH2Cl2从水相中萃取(2x)。将合并的有机相用1N NaHSO4洗涤(2x),用Na2SO4干燥,过滤并浓缩。将粗物质通过快速柱色谱纯化(SiO2,0→20%丙酮在己烷中),得到作为无色油状物的标题化合物(501mg,87%):IR(薄膜)2899.51,1451.42,1105.09,1091.88cm-1;1H NMR(400MHz,CDCl3)δ7.39-7.31(m,5H),4.53(d,J=11.9Hz,1H),4.47(d,J=11.9Hz,1H),3.73(qd,J=6.2,2.2Hz,1H),3.50(s,3H),2.84(d,J=2.3Hz,1H),2.03-1.85(d,J=3.4Hz,3H),1.81-1.47(m,12H),1.24(d,J=6.3Hz,3H);13CNMR(101MHz,CDCl3)δ138.99,128.30,127.48,127.35,91.85,75.25,70.22,61.34,38.89,37.27,37.18,28.40,15.91;HRMS-ESI m/z(([M+Na]+)),对于C21H30NaO2,计算值为337.2138;实测值为337.2143。
实施例4H:制备((((2S)-1-(环戊-2-烯-1-基氧基)丙-2-基)氧基)-甲基)苯。
向(S)-2-(苄氧基)丙-1-醇(300mg,1.81mmol)、DPPF(100mg,0.180mmol)、和Pd2(dba)3(83mg,0.090mmol)在无水THF(9mL)的65℃溶液中添加碳酸叔丁基环戊-2-烯-1-基酯(665mg,3.61mmol),将反应混合物在65℃搅拌7h,冷却至室温,浓缩,并通过快速柱色谱纯化(SiO2,1→16%丙酮在己烷中),得到作为淡黄色油状物的标题化合物(192mg,0.826mmol,45.7%)。1H NMR和13C NMR显示产物是非对映异构体的1∶1混合物,这是由13C谱中存在另外的碳所反映出来的:1H NMR(400MHz,CDCl3)δ7.42-7.30(m,4H),7.30-7.19(m,1H),6.01(dtd,J=5.6,2.2,1.1Hz,1H),5.91-5.81(m,1H),4.70-4.53(m,3H),3.78-3.64(m,1H),3.54(ddd,J=11.3,9.9,5.8Hz,1H),3.41(ddd,J=9.8,7.4,5.1Hz,1H),2.56-2.42(m,1H),2.32-2.20(m,1H),2.20-2.07(m,1H),1.86-1.72(m,1H),1.20(d,J=6.3Hz,3H);13CNMR(126MHz,CDCl3)δ139.02,135.64,135.60,130.86,130.78,128.28,127.61,127.60,127.37,85.27,74.24,74.22,72.52,72.46,71.17,31.10,31.09,29.66,29.60,17.56,17.54;ESIMS m/z 255.3(([M+Na]+))。
实施例5:制备3-(((2S,3R)-2-(苄氧基)-4-乙基己-3-基)氧基)-1,1′-联苯。
通过在温和真空下抽真空并回充N2(3x)将1-(((2S,3R)-2-(苄氧基)-4-乙基己-3-基)氧基)-3-溴苯(555mg,1.418mmol)、碳酸钠(Na2CO3;451mg,4.25mmol)、和苯基硼酸(501mg,4.11mmol)在二氧杂环己烷(5.3mL)和H2O(1.8mL)中的混合物脱氧,将脱氧的混合物用四(三苯基膦)钯(0)(Pd(PPh3)4;164mg,0.142mmol)处理。重复脱气过程,将混合物加热至80℃并在80℃搅拌4h,将其冷却至室温,并用H2O(20mL)稀释。将各相分离,将水相用CH2Cl2(20mL)萃取。如下干燥有机相:使其穿过相分离器滤芯,然后蒸发。将所得油状物通过快速柱色谱纯化(SiO2,1→5%EtOAc在己烷中),得到作为无色油状物的标题化合物(540mg,98%):IR(薄膜)2961,2931,2873,1595,1569,1476cm-1;1H NMR(500MHz,CDCl3)δ7.58-7.51(m,2H),7.42-7.37(m,2H),7.36-7.27(m,7H),7.23(dd,J=2.5,1.7Hz,1H),7.14(ddd,J=7.6,1.7,1.0Hz,1H),6.97(ddd,J=8.2,2.6,0.9Hz,1H),4.63(d,J=11.6Hz,1H),4.48(d,J=11.7Hz,1H),4.42(t,J=5.1Hz,1H),3.82(qd,J=6.2,5.2Hz,1H),1.75-1.56(m,2H),1.46-1.35(m,3H),1.30(d,J=6.2Hz,3H),0.91(t,J=7.4Hz,3H),0.89(t,J=7.4Hz,3H);13C NMR(126MHz,CDCl3)δ160.44,142.57,141.18,138.56,129.60,128.66,128.30,127.62,127.46,127.24,127.13,119.38,114.98,114.77,81.99,75.43,70.76,43.00,22.36,21.44,15.70,11.85,11.44。
实施例6A,步骤1:制备(3S,4R,5S)-5-(苄氧基)-3-(4-氟苄基)-4-苯氧基己-1-醇。
向9-硼杂双环[3.3.1]壬烷的溶液(9-BBN;17.90mL,8.95mmol,0.5M在THF中)中添加1-((2S,3R,4S)-4-(苄氧基)-3-苯氧基-2-乙烯基戊基)-4-氟苯(2.33g,5.97mmol),将反应混合物在室温搅拌2h,冷却至0℃,并用2N NaOH水溶液(11.9mL,23.9mmol)然后用30%H2O2(2.44mL,23.9mmol)逐滴处理。将混合物从冷浴中取出并搅拌45min,冷却回0℃,并通过添加亚硫酸氢钠饱和水溶液(NaHSO3)而将其淬灭。将各相分离,将水相用EtOAc(3 x 20mL)萃取。将合并的有机相用MgSO4干燥,过滤,并蒸发,得到油状物,将其通过快速柱色谱纯化(SiO2,4→20%丙酮在己烷中),得到作为透明无色油状物的标题化合物(2.32g,95%):1HNMR(400MHz,CDCl3)δ7.36(d,J=4.5Hz,4H),7.34-7.27(m,1H),7.27-7.18(m,2H),7.11-7.03(m,2H),6.97-6.87(m,3H),6.85-6.76(m,2H),4.67(d,J=11.4Hz,1H),4.41(d,J=11.4Hz,1H),4.31(dd,J=7.5,2.4Hz,1H),3.97-3.80(m,1H),3.56(p,J=6.0Hz,2H),3.00(dd,J=13.8,6.2Hz,1H),2.55(dd,J=13.8,8.7Hz,1H),2.29(pd,J=8.3,2.4Hz,1H),1.76-1.61(m,1H),1.58-1.48(m,2H),1.28(d,J=6.1Hz,3H);13C NMR(101MHz,CDCl3)δ162.54,160.11,158.77,138.25,136.81,136.78,130.72,130.64,129.60,128.47,127.96,127.76,120.95,115.63,115.13,114.92,81.00,75.19,70.83,61.34,39.38,35.90,33.50,16.82;ESIMS m/z 431(([M+Na]+))。
实施例6A,步骤2a:制备1-((2S,3R,4S)-4-(苄氧基)-2-(2-甲氧基乙基)-3-苯氧基戊基)-4-氟苯。
向(3S,4R,5S)-5-(苄氧基)-3-(4-氟苄基)-4-苯氧基己-1-醇(390mg,0.955mmol)在无水CH2Cl2(10mL)的0℃溶液中添加N1,N1,N8,N8-四甲基萘-1,8-二胺(614mg,2.86mmol)然后添加三甲基氧鎓四氟硼酸盐(282mg,1.91mmol),将混合物在0℃搅拌4h,并通过添加1NHCl水溶液(10mL)而将其淬灭。将各相分离,将水相用CH2Cl2(2 x 10mL)萃取。将有机相合并,用Na2SO4干燥,过滤,并蒸发成油性白色固体,使其悬浮在己烷中,过滤通过并浓缩,得到油状物。将残余油状物通过快速柱色谱纯化(SiO2,1→20%丙酮在己烷中),得到作为透明无色油状物的标题化合物(239mg,59%):1H NMR(400MHz,CDCl3)δ7.35(d,J=4.1Hz,4H),7.30(dt,J=9.1,4.5Hz,1H),7.22(t,J=8.0Hz,2H),7.08(dd,J=8.2,5.7Hz,2H),6.98-6.87(m,3H),6.83(d,J=8.4Hz,2H),4.65(d,J=11.5Hz,1H),4.41(d,J=11.5Hz,1H),4.32(dd,J=7.0,2.5Hz,1H),3.85(p,J=6.2Hz,1H),3.29(t,J=6.8Hz,2H),3.19(d,J=1.3Hz,3H),3.01(dd,J=13.8,5.9Hz,1H),2.56(dd,J=13.9,8.8Hz,1H),2.37-2.22(m,1H),1.78-1.64(m,1H),1.59-1.47(m,1H),1.27(d,J=6.1Hz,3H);13C NMR(126MHz,CDCl3)δ161.27(d,J=243.4Hz),159.11,138.44,136.89(d,J=3.2Hz),130.65(d,J=7.7Hz),129.46,128.38,127.76,127.59,120.70,115.73,114.93(d,J=21.0Hz),81.11,75.18,71.07,70.74,58.39,39.20,35.38,30.20,16.67;ESIMS m/z 423(([M+H]+))。
实施例6A,步骤2b:制备1-((2S,3R,4S)-4-(苄氧基)-2-(2-(叔丁氧基)乙基)-3-苯氧基戊基)-4-甲氧基苯。
向(3S,4R,5S)-5-(苄氧基)-3-(4-甲氧基苄基)-4-苯氧基己-1-醇(1.99g,4.73mmol)和(R)-氮丙啶-1,2-二甲酸2-苄基1-叔丁基酯(1.44g,5.21mmol)在无水CH2Cl2(20mL)的0℃溶液中添加Sc(OTf)3(0.233g,0.473mmol),将反应混合物在0℃搅拌40min,然后随着冰融化使反应混合物经历一夜升温至室温。将混合物用NaHCO3饱和水溶液(25mL)淬灭,在H2O(25mL)和CH2Cl2(50mL)之间分配,将各相分离。将水相用CH2Cl2(2 x 25mL)萃取,将合并的有机相用Na2SO4干燥,过滤,并蒸发成无色油状物,将其通过快速柱色谱纯化(SiO2,2→25%丙酮在己烷中),得到作为无色油状物的标题化合物(320mg,14%):1H NMR(400MHz,CDCl3)δ7.34(d,J=4.4Hz,4H),7.33-7.26(m,1H),7.21(t,J=8.0Hz,2H),7.07(d,J=8.6Hz,2H),6.88(t,J=8.6Hz,3H),6.79(d,J=8.6Hz,2H),4.63(d,J=11.5Hz,1H),4.45-4.36(m,2H),3.86(p,J=6.2Hz,1H),3.78(s,3H),3.32-3.18(m,2H),2.99(dd,J=13.9,5.8Hz,1H),2.54(dd,J=13.9,8.8Hz,1H),2.37-2.22(m,1H),1.66(dq,J=14.0,7.0Hz,1H),1.60-1.46(m,1H),1.27(d,J=6.1Hz,3H),1.08(s,9H);13C NMR(151MHz,CDCl3)δ159.44,157.75,138.64,133.45,130.26,129.37,128.32,127.68,127.47,120.52,115.94,113.63,81.62,75.33,72.50,70.73,60.26,55.29,39.62,35.32,31.25,27.51,16.62;ESIMS m/z 499(([M+Na]+))。
实施例6B,步骤1:制备(2S,3S,4S)-4-(苄氧基)-3-苯氧基-2-丙氧基戊-1-醇。
在-78℃将(((2S,3S,4S)-2-(苄氧基)-4-丙氧基己-5-烯-3-基)氧基)苯(500mg,1.47mmol)和NaHCO3(12.3mg,0.147mmol)在无水MeOH(0.44mL)和CH2Cl2(14mL)中的溶液用臭氧(O3)处理,直到溶液从无色变为蓝色。将反应混合物用氧气(O2)吹洗直到呈无色,将其用另外的MeOH(4mL)然后用NaBH4(167mg,4.41mmol)处理,然后使其升温至室温并搅拌4h。将混合物用H2O淬灭,用CH2Cl2稀释,将各相分离。将水相用CH2Cl2萃取(2x),将合并的有机相用盐水洗涤,用MgSO4干燥,过滤,并蒸发。将所得粗制残余物通过快速柱色谱纯化(SiO2,0→100%EtOAc在己烷中),得到作为无色油状物的标题化合物(458mg,91%):IR(薄膜)3453,2934,2875,1597,1493,1237cm-1;1H NMR(400MHz,CDCl3)δ7.36-7.22(m,7H),7.06-7.02(m,2H),6.97-6.91(m,1H),4.63(d,J=11.5Hz,1H),4.51-4.44(m,2H),3.95-3.87(m,1H),3.79-3.66(m,3H),3.60-3.49(m,2H),2.08-2.04(m,1H),1.60-1.51(m,2H),1.29(d,J=6.3Hz,3H),0.86(t,J=7.4Hz,3H);ESIMS m/z 345(([M+H]+))。
实施例6B,步骤2:制备(((2S,3S,4S)-4-(苄氧基)-1-甲氧基-2-丙氧基戊-3-基)氧基)苯。
将(2S,3S,4S)-4-(苄氧基)-3-苯氧基-2-丙氧基戊-1-醇(452mg,1.31mmol)、Proton (1687mg,7.87mmol)、和三甲基氧鎓四氟硼酸盐(485mg,3.28mmol)在无水CH2Cl2(10mL)中的溶液在室温搅拌8h,通过添加NaHCO3饱和水溶液将反应混合物淬灭,用CH2Cl2稀释,将各相分离。将水相用CH2Cl2萃取,将合并的有机相用1M HCl水溶液洗涤(3x),用盐水洗涤,用MgSO4干燥,过滤,并蒸发。将残余物通过快速柱色谱纯化(SiO2,0→100%EtOAc在己烷中),得到作为无色油状物的标题化合物(370mg,79%):IR(薄膜)2930,2875,1597,1493,1237cm-1;1H NMR(400MHz,CDCl3)δ7.35-7.21(m,7H),7.08-7.03(m,2H),6.95-6.89(m,1H),4.64(d,J=11.5Hz,1H),4.50-4.44(m,2H),4.02-3.93(m,1H),3.89-3.83(m,1H),3.64-3.56(m,1H),3.54-3.48(m,1H),3.47-3.39(m,2H),3.24(s,3H),1.63-1.53(m,2H),1.26(d,J=6.3Hz,3H),0.87(t,J=7.4Hz,3H);ESIMS m/z 359(([M+H]+))。
实施例6C:制备(((1S,2S,3S)-3-(苄氧基)-1-环丙基-1-丙氧基丁-2-基)氧基)苯。
在0℃向(((2S,3S,4S)-2-(苄氧基)-4-丙氧基己-5-烯-3-基)氧基)苯(500mg,1.47mmol)和二乙基锌(Et2Zn;1M在己烷中,14.7mL,14.7mmol)在Et2O(10mL)的溶液中逐滴添加二碘甲烷(CH2I2;2.37mL,29.4mmol),历时15min的时间段将反应混合物升温至室温,并将其搅拌2d。在0℃添加过量的Et2Zn(5.0mL,5.0mmol)和CH2I2(0.83mL,10.3mmol),将反应升温至45℃并在45℃搅拌20h。通过添加NH4Cl饱和水溶液将反应混合物淬灭,将其用Et2O萃取。将合并的有机萃取物用盐水洗涤,用MgSO4干燥,过滤,浓缩,并通过柱色谱纯化(SiO2,己烷/EtOAc梯度),得到作为无色油状物的标题化合物(113mg,22%):IR(无底物)2932,2874,1597,1493,1239,1084cm-1;1H NMR(400MHz,CDCl3)δ7.39-7.20(m,7H),7.09-7.04(m,2H),6.94-6.88(m,1H),4.62(d,J=11.4Hz,1H),4.47(d,J=11.4Hz,1H),4.35(dd,J=7.3,2.9Hz,1H),4.08-4.00(m,1H),3.82-3.74(m,1H),3.35-3.28(m,1H),2.98(dd,J=9.0,2.9Hz,1H),1.66-1.55(m,2H),1.26(d,J=6.2Hz,3H),0.98-0.85(m,4H),0.70-0.62(m,1H),0.49-0.41(m,1H),0.38-0.30(m,1H),0.21-0.13(m,1H);HRMS-ESI(m/z)[M]+,对于C23H30O3,计算值为354.2195;实测值为354.2195。
实施例7,步骤1:制备(2R,3S)-3-(苄氧基)-2-苯氧基丁-1-醇。
向(((2S,3R,E)-2-(苄氧基)己-4-烯-3-基)氧基)苯(740mg,2.62mmol)在CH2Cl2(11mL)和MeOH(1.2mL)的混合物的溶液中添加2滴1%苏丹III在CH2Cl2的溶液。将所得粉色溶液冷却至-78℃,并将O3鼓泡通过反应混合物,直到粉色褪去。将溶液用O2吹洗5min,置于N2气氛下,并用NaBH4(297mg,7.86mmol)处理。将反应混合物缓慢升温至室温,搅拌过夜,用CH2Cl2(10mL)稀释,并用饱和水溶液NH4Cl(10mL)淬灭。将各相分离,将水相用CH2Cl2(2x10mL)萃取,通过使合并的有机相穿过相分离器滤芯并蒸发而将其干燥。将所得粗物质通过快速柱色谱纯化(SiO2,0→60%EtOAc在己烷中),得到作为无色油状物的标题化合物(610mg,85%):1H NMR(400MHz,CDCl3)δ7.37-7.25(m,7H),7.01-6.92(m,3H),4.67(d,J=11.6Hz,1H),4.55(d,J=11.5Hz,1H),4.23(app dt,J=6.0,4.5Hz,1H),3.97-3.84(m,3H),2.30(app t,J=6.4Hz,1H),1.31(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ158.01,138.07,129.66,128.49,127.82,127.81,121.49,116.16,81.18,75.24,71.51,62.02,16.82;ESIMS m/z 273(([M+H]+))。
实施例7,步骤2a:制备(((2R,3S)-3-(苄氧基)-1-丙氧基丁-2-基)氧基)苯。
向(2R,3S)-3-(苄氧基)-2-苯氧基丁-1-醇(150mg,0.551mmol)在DMF(2.7mL)的0℃溶液中添加NaH(44.1mg,1.10mmol,60wt%在矿物油中),将反应混合物在0℃搅拌10min,从冷浴中取出,并在室温搅拌15min,将其用4-甲基苯磺酸丙基酯(237μL,1.24mmol)处理,并在室温搅拌16h。通过添加饱和水溶液NH4Cl(7mL)将混合物淬灭,将其用Et2O(10mL)稀释,将各相分离。将水相用Et2O(2 x 10mL)萃取,将合并的有机相用盐水洗涤(5mL),用Na2SO4干燥,过滤并蒸发。将粗制残余物通过快速柱色谱纯化(SiO2,0→30%EtOAc在己烷中),得到作为无色油状物的标题化合物(125mg,72%):1H NMR(400MHz,CDCl3)δ7.35-7.22(m,7H),7.03-6.90(m,3H),4.67-4.54(m,2H),4.36(app td,J=5.1,3.9Hz,1H),3.89(qd,J=6.4,5.0Hz,1H),3.80-3.67(m,2H),3.41(app td,J=6.7,2.6Hz,2H),1.64-1.50(m,2H),1.29(d,J=6.4Hz,3H),0.89(app t,J=7.4Hz,3H);13C NMR(101MHz,CDCl3)δ158.67,138.64,129.41,128.32,127.69,127.51,121.09,116.52,80.85,74.38,73.30,71.46,69.48,22.87,16.26,10.58;ESIMS m/z 315(([M+H]+))。
实施例7,步骤2b:制备(((2R,3S)-3-(苄氧基)-1-苯氧基丁-2-基)氧基)苯。
向(2R,3S)-3-(苄氧基)-2-苯氧基丁-1-醇(290mg,1.06mmol)在CH2Cl2(5.3mL)的溶液中添加乙酸铜(19.3mg,0.106mmol)和Ph3Bi(OAc)2(654mg,1.17mmol),将混合物在室温搅拌过夜,将其过滤通过短柱并用CH2Cl2(2 x 10mL)冲洗,并浓缩。将粗制残余物通过快速柱色谱纯化(SiO2,0→35%EtOAc在己烷中),得到作为无色油状物的标题化合物(290mg,76%):1H NMR(400MHz,CDCl3)δ7.31-7.24(m,9H),7.04-6.83(m,6H),4.66(d,J=11.7Hz,1H),4.61-4.50(m,2H),4.34-4.21(m,2H),4.01(qd,J=6.3,5.3Hz,1H),1.36(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ158.72,158.40,138.34,129.53,129.43,128.37,127.80,127.62,121.44,120.93,116.56,114.70,80.25,74.09,71.58,66.73,16.46;ESIMSm/z 371(([M+Na]+))。
实施例8A:制备(1R,2S)-1-(3-氯苯氧基)-1-环戊基丙-2-醇。
向1-((1R,2S)-2-(苄氧基)-1-环戊基丙氧基)-3-氯苯(630mg,1.83mmol)在乙醇(EtOH;6.1mL)和环己烯(3.0mL)的混合物的溶液中添加10%钯碳(Pd/C;97mg,0.091mmol),将所得悬浮液加热至65℃并在65℃搅拌2h。将反应混合物过滤通过短柱,将滤液蒸发,得到作为无色油状物的标题化合物(476mg,97%):IR(薄膜)3351,2951,2867,1590,1473,1427,1228cm-1;1H NMR(500MHz,CDCl3)δ7.17(t,J=8.1Hz,1H),7.03(t,J=2.3Hz,1H),6.94-6.87(m,2H),4.21(dd,J=8.0,3.4Hz,1H),3.99(qd,J=6.4,3.3Hz,1H),2.21-2.07(m,1H),1.87-1.77(m,1H),1.70(dtd,J=11.7,7.6,3.8Hz,1H),1.66-1.44(m,5H),1.38-1.30(m,1H),1.27(d,J=6.4Hz,3H),1.31-1.19(m,1H);13C NMR(126MHz,CDCl3)δ160.86,134.83,130.23,121.13,116.87,114.59,86.65,69.41,42.15,29.68,29.22,25.23,25.03,17.85。
实施例8B:制备(2S,3R,4R)-4-苄基-3-异丁氧基己-2-醇。
向帕尔瓶中装入((((2S,3R,4S)-4-苄基-3-((2-甲基烯丙基)氧基)己-5-烯-2-基)氧基)甲基)苯(1.85g,5.28mmol)和10%Pd/C(0.056g,0.53mmol)在EtOH(10mL)中的悬浮液,将该瓶在温和真空下抽真空并回充氢气(H2;3x)。将瓶装进帕尔振荡器中,用H2将系统加压至50磅每平方英寸(psi),将其在室温搅动过夜。将反应混合物过滤通过将滤液蒸发,得到作为无色油状物的标题化合物(1.36g,97%):1H NMR(400MHz,CDCl3)δ7.30-7.24(m,2H),7.22-7.14(m,3H),3.96(h,J=6.3Hz,1H),3.39(dd,J=8.6,6.3Hz,1H),3.30(dd,J=8.6,6.6Hz,1H),3.21-3.17(m,1H),3.05(dd,J=13.8,4.6Hz,1H),2.44(dd,J=13.8,9.8Hz,1H),1.86(m,2H),1.76(d,J=5.6Hz,1H),1.45-1.24(m,2H),1.25(d,J=6.3Hz,3H),0.95(dd,J=6.7,4.3Hz,6H),0.85(t,J=7.5Hz,3H);13C NMR(100MHz,CDCl3)δ142.04,129.13,128.19,125.59,83.76,79.27,68.23,42.93,35.69,29.24,22.76,19.54,19.50,19.02,11.30;[α]=3.048(2.1g/100mL,CHCl3)。
实施例8C:制备(2S,3R)-4-(环戊基甲基)-3-(环丙基甲氧基)己-2-醇。
向1-((2S,3R,4S)-4-(苄氧基)-2-(2-甲氧基乙基)-3-苯氧基戊基)-4-氟苯(215mg,0.509mmol)在EtOAc(5mL)的溶液中添加5%Pd/C(54.2mg,0.025mmol),将反应容器在温和真空下抽真空并回充H2(3x)。将混合物置于约1Atm的H2(气球)下并在室温搅拌过夜。将反应混合物过滤通过短柱并浓缩,得到作为透明无色油状物的标题化合物(176mg,99%):1H NMR(400MHz,CDCl3)δ7.30-7.21(m,2H),7.21-7.14(m,2H),7.02-6.85(m,5H),4.26(dd,J=6.2,3.9Hz,1H),4.11(h,J=6.2Hz,1H),3.40-3.24(m,2H),3.21(s,3H),3.11(dd,J=13.9,5.5Hz,1H),2.55(dd,J=14.0,9.0Hz,1H),2.37-2.23(m,1H),1.80-1.66(m,2H),1.66-1.54(m,1H),1.29(d,J=6.3Hz,3H);13C NMR(126MHz,CDCl3)δ161.31(d,J=243.7Hz),159.11,136.75(d,J=3.2Hz),130.55(d,J=7.7Hz),129.57,120.97,115.83,115.07(d,J=21.0Hz),82.44,70.82,68.31,58.46,39.14,35.48,30.06,20.18;ESIMS m/z333(([M+H]+))。
实施例8D:制备(1S,2S)-1-苯氧基-1-(噻吩-2-基)丙-2-醇。
向2-((1S,2S)-2-((4-甲氧基苄基)氧基)-1-苯氧基丙基)噻吩(0.223g,0.630mmol)在CH2Cl2(3mL)和H2O(0.3mL)的混合物的0℃溶液中添加4,5-二氯-3,6-二氧代环己-1,4-二烯-1,2-二甲腈(0.150g,0.661mmol),将反应混合物搅拌30min,通过添加1NNaOH水溶液(0.66mL)将其淬灭,并用CH2Cl2(10mL)稀释。将各相分离,将水相用CH2Cl2(2 x10mL)萃取。将合并的有机相用Na2SO4干燥,过滤,蒸发,并通过快速柱色谱纯化(SiO2,2→20%丙酮在己烷中),得到作为无色油状物的标题化合物(116mg,75%):IR(薄膜)3390,2923,2851,2865,1597cm-1;1H NMR(300MHz,CDCl3)δ7.33-7.16(m,3H),7.07(ddd,J=3.5,1.2,0.7Hz,1H),7.03-6.88(m,4H),5.26(d,J=4.9Hz,1H),4.28-4.09(m,1H),2.08(d,J=4.9Hz,1H),1.29(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ157.60,140.58,129.43,126.59,126.50,125.94,121.60,116.21,80.60,70.73,18.33。
实施例8E:制备(2S,3R)-3-(苄氧基)己-5-烯-2-醇。
历时5min的时间段向(((2S,3R)-3-(苄氧基)己-5-烯-2-基)氧基)三异丙基硅烷(4.04g,11.1mmol)在THF(56mL)的0℃溶液中添加四-N-丁基氟化铵(TBAF;14.7mL,14.7mmol,1M在THF中),将反应混合物升温至室温并搅拌4h,将其倒入饱和水溶液NH4Cl(100mL)中,并用EtOAc(100mL)稀释。将各相分离,将水相用EtOAc(2 x 100mL)萃取。将合并的有机相用MgSO4干燥,过滤,并浓缩成黄色油状物,将其通过快速柱色谱纯化(SiO2,0→25%EtOAc在己烷中),得到作为透明无色油状物的标题化合物(1.91g,83%):IR(无底物)3419,2977,2872,1454,1069,696cm-1;1H NMR(400MHz,CDCl3)δ7.39-7.20(m,5H),5.87(ddt,J=17.2,10.2,7.1Hz,1H),5.18-5.09(m,1H),5.06(ddt,J=10.1,2.2,1.2Hz,1H),4.62(d,J=11.5Hz,1H),4.55(d,J=11.5Hz,1H),4.00-3.82(m,1H),3.40(ddd,J=7.3,5.2,3.8Hz,1H),2.41(dtt,J=14.3,7.1,1.4Hz,1H),2.33-2.23(m,1H),2.21(s,1H),1.17(d,J=6.5Hz,3H);HRMS-ESI(m/z)([M+H]+),对于C13H19O2,计算值为207.1380;实测值为207.1372。
实施例8F:制备(2S,3R)-3-(对-甲苯基氧基)丁-2-醇。
向4-(((2R,3S)-3-(苄氧基)丁-2-基)氧基)-2-氯-1-甲基苯(330mg,1.08mmol)在EtOH(11mL)的溶液中添加NEt3(0.30mL,2.17mmol)、10%Pd/C(58mg,0.054mmol),将反应容器抽真空并回充H2(3x)。将混合物在H2下在室温搅拌24h,将其过滤通过短柱,并浓缩,得到油性固体。使残余物悬浮在CH2Cl2(20mL)中,将其用1N HCl(20mL)洗涤,用Na2SO4干燥,过滤,并浓缩,得到312mg无水油状物,将其溶解于EtOH∶环己烯的2∶1混合物(10mL)中,用10%Pd/C(58mg,0.054mmol)处理,将其升温至65℃并在65℃搅拌20h。将混合物冷却至室温,过滤通过短柱,并浓缩,得到作为无色油状物的标题化合物(188mg,96%):IR(薄膜)3391,2977,2923,1613,1585,1508,1450,1373,1287,1232,1167,1082,1050,1008,993,935,901,813,746cm-1;1H NMR(300MHz,CDCl3)δ7.08(d,J=8.2Hz,2H),6.91-6.68(m,2H),4.27(qd,J=6.3,3.3Hz,1H),4.02(dd,J=6.2,3.3Hz,1H),2.29(s,3H),2.07(s,1H),1.25(d,J=5.6Hz,3H),1.23(d,J=5.8Hz,3H);13C NMR(126MHz,CDCl3)δ155.35,130.51,130.00,116.18,77.60,69.37,20.48,17.83,13.45。
实施例8G:制备(2S,3S,4S)-4-环丙基-3-苯氧基-4-丙氧基丁-2-醇。
向高压钢反应器中装入(((1S,2S,3S)-3-(苄氧基)-1-环丙基-1-丙氧基丁-2-基)氧基)苯(112mg,0.316mmol)在EtOH(10mL)的溶液、10%Pd/C、Degussa类型(17mg,0.016mmol)、和3滴AcOH,向反应器装入600 psi的H2,将其加热至50℃并在50℃剧烈搅拌14h。将反应混合物过滤通过短柱,浓缩,将残余物用EtOAc稀释并用饱和水溶液NaHCO3洗涤。将水相用EtOAc进一步萃取,将合并的有机相用盐水洗涤,用Na2SO4干燥,过滤,并浓缩,得到作为无色油状物的标题化合物(66.0mg,79%):IR(无底物)3448,2963,2932,1597,1492,1238,1079cm-1;1H NMR(400MHz,CDCl3)δ7.31-7.25(m,2H),7.01-6.98(m,2H),6.98-6.93(m,1H),4.34-4.25(m,1H),4.20(dd,J=7.0,3.3Hz,1H),3.80-3.72(m,1H),3.47-3.40(m,1H),3.33(d,J=4.2Hz,1H),3.11(dd,J=8.2,3.3Hz,1H),1.66-1.57(m,2H),1.27(d,J=6.2Hz,3H),1.14-1.04(m,1H),0.93(t,J=7.4Hz,3H),0.71-0.63(m,1H),0.53-0.45(m,1H),0.45-0.38(m,1H),0.26-0.14(m,1H);HRMS-ESI(m/z)[M]+,对于C16H24O3,计算值为264.1725;实测值为264.1723。
实施例9,步骤1:制备(R)-1-((R)-2,2-二甲基-1,3-二氧杂戊环-4-基)-2-甲基丙-1-醇
向异丙基氯化镁(62mL,125mmol,2M在THF中)和硼氢化锂(LiBH4;41mL,81mmol,2M在THF中)在无水THF(350mL)的-5℃溶液中逐滴添加(R)-2,2-二甲基-1,3-二氧杂戊环-4-甲酸甲酯(10g,62mmol),其添加速率可保持温度低于5℃。将反应混合物经历一夜缓慢升温至室温,冷却至0℃,并通过添加H2O将其小心淬灭。将各相分离,将水相用Et2O萃取。将有机相合并,用Na2SO4干燥,过滤,并浓缩成无色油状物,将其通过快速柱色谱纯化(SiO2,0→10%丙酮在己烷中),得到作为无色油状物的标题化合物(5.07g,47%):1H NMR(400MHz,CDCl3)δ4.21-4.10(m,1H),4.02(dd,J=8.0,6.5Hz,1H),3.76(dd,J=8.0,7.2Hz,1H),3.23(dt,J=6.2,5.3Hz,1H),2.13(d,J=6.3Hz,1H),1.76-1.62(m,1H),1.44(s,3H),1.38(s,3H),0.98(d,J=6.8Hz,6H);13C NMR(101MHz,CDCl3)δ109.17,76.86,76.30,66.55,31.56,26.60,25.44,19.41,17.49;ESIMS m/z 174(([M+H]+))。
实施例9,步骤2:制备(R)-4-((R)-1-(3-氯苯氧基)-2-甲基丙基)-2,2-二甲基-1,3-二氧杂戊环。
向(R)-1-((R)-2,2-二甲基-1,3-二氧戊环-4-基)-2-甲基丙-1-醇(5.62g,32.3mmol)在无水DMF(32mL)的溶液中一次性添加KOt-Bu(4.34g,38.7mmol),将反应混合物在室温搅拌5min,用1-氯-3-氟苯(10.3mL,97mmol)处理,将其加热至55℃并在55℃搅拌约3h。向混合物中添加另外的KOt-Bu(1.8g,16.1mmol)和1-氯-3-氟苯(3.45mL,32.3mmol),继续在55℃搅拌,直到薄层色谱(TLC)表明起始物质完全消耗。将反应混合物在Et2O和H2O之间分配,将各相分离。将有机相用H2O洗涤(2x),用Na2SO4干燥,过滤,并蒸发。将粗物质通过快速柱色谱纯化(SiO2,0→5%丙酮在己烷中),得到作为无色油状物的标题化合物(8.97g,98%):1H NMR(400MHz,CDCl3)δ7.16(t,J=8.2Hz,1H),7.03(t,J=2.2Hz,1H),6.93-6.86(m,2H),4.37(dt,J=7.6,6.4Hz,1H),4.07-4.00(m,2H),3.68(t,J=7.9Hz,1H),1.98-1.85(m,1H),1.45(s,3H),1.37(s,3H),1.01(d,J=6.8Hz,3H),0.99(d,J=6.8Hz,3H);13C NMR(101MHz,CDCl3)δ160.96,134.64,130.08,121.03,116.81,114.66,109.40,83.92,65.99,30.69,26.41,25.58,19.84,17.35;EIMS m/z 284。
实施例9,步骤3:制备(R)-2,2-二甲基-4-((R)-2-甲基-1-苯氧基丙基)-1,3-二氧杂戊环。
向(R)-4-((R)-1-(3-氯苯氧基)-2-甲基丙基)-2,2-二甲基-1,3-二氧杂戊环(9.44g,33.1mmol)在无水乙醇(95mL)的溶液中添加5%Pd/C(3.53g,1.66mmol)和NEt3(13.1mL,99mmol),将H2鼓泡通过溶液几分钟。将反应混合物在约1个大气压(Atm)的H2(气球)下放置并在室温搅拌过夜。将混合物过滤通过用Et2O冲洗,将滤液用0.1N HCl水溶液(3x)洗涤,用Na2SO4干燥,过滤,并蒸发,得到作为无色油状物的标题化合物(7.12g,86%)。1H NMR(400MHz,CDCl3)δ7.28-7.22(m,2H),7.00(dt,J=7.9,1.1Hz,2H),6.92(tt,J=7.3,1.1Hz,1H),4.39(dt,J=7.8,6.1Hz,1H),4.09-3.98(m,2H),3.71(t,J=8.0Hz,1H),2.01-1.91(m,1H),1.45(s,3H),1.37(s,3H),1.03(d,J=6.9Hz,3H),1.00(d,J=6.9Hz,3H);13C NMR(101MHz,CDCl3)δ160.19,129.35,120.85,116.27,109.23,83.12,65.99,30.74,26.43,25.67,19.83,17.76;EIMS m/z 250。
实施例10,步骤1:制备(2R,3R)-4-甲基-3-苯氧基戊烷-1,2-二醇。
向(R)-2,2-二甲基-4-((R)-2-甲基-1-苯氧基丙基)-1,3-二氧杂戊环(7.1g,28.4mmol)在THF(50mL)的溶液中添加1N HCl水溶液(50mL),将反应混合物剧烈搅拌过夜并用Et2O稀释。将各相分离,将水相用Et2O萃取。然后将合并的有机相依次用饱和水溶液NaHCO3和盐水洗涤,用Na2SO4干燥,过滤,并蒸发。将粗制残余物通过快速柱色谱纯化(SiO2,0→50%丙酮在己烷中),得到作为白色固体的标题化合物(5.44g,91%):1H NMR(400MHz,CDCl3)δ7.30-7.20(m,2H),6.99-6.90(m,3H),4.14(dd,J=5.8,4.3Hz,1H),3.97-3.88(m,1H),3.68-3.55(m,2H),2.71(d,J=6.4Hz,1H),2.51(t,J=5.8Hz,1H),2.15-2.04(m,1H),0.99(d,J=6.8,1.6Hz,6H);13C NMR(101MHz,CDCl3)δ159.62,129.63,121.25,115.99,82.58,72.12,64.12,30.01,19.44,18.03;EIMS m/z 210。
实施例10,步骤2,3a和3b:制备(R)-3-甲基-2-苯氧基丁-1-醇和(3S,4R)-5-甲基1-4-苯氧基己-3-醇。
步骤2:
向(2R,3R)-4-甲基-3-苯氧基戊烷-1,2-二醇(0.5g,2.38mmol)在CH2Cl2(4mL)和NaHCO3饱和水溶液(1mL)的溶液中添加高碘酸钠(2.034g,9.51mmol),将混合物剧烈搅拌,直到TLC显示二醇完全消耗。将反应混合物过滤,将滤液用H2O洗涤,用Na2SO4干燥,过滤,并浓缩,得到中间体醛,即(R)-3-甲基-2-苯氧基丁醛,其无需进一步纯化即可使用。
步骤3a:
向粗制(R)-3-甲基-2-苯氧基丁醛(~1mmol)在MeOH(3.3mL)的溶液中一次性添加NaBH4(76mg,2.0mmol),将混合物搅拌,直到TLC显示醛完全消耗。将反应混合物用饱和水溶液NH4Cl(10mL)小心淬灭,用CH2Cl2稀释,将各相分离。将水相用CH2Cl2萃取(2x),通过使合并的有机相穿过相分离器滤芯而将其干燥。将溶剂蒸发,将所得粗物质通过快速柱色谱纯化(SiO2,0→15%丙酮在己烷中),得到作为无色油状物的标题化合物(170mg,94%):1H NMR(400MHz,CDCl3)δ7.32-7.24(m,2H),7.00-6.91(m,3H),4.15(td,J=6.1,3.6Hz,1H),3.88-3.73(m,2H),2.14-2.01(m,1H),1.80(dd,J=7.3,5.6Hz,1H),1.01(d,J=6.9Hz,3H),0.97(d,J=6.9Hz,3H);13C NMR(101MHz,CDCl3)δ158.86,129.57,121.18,116.35,83.94,62.27,29.25,18.62,18.09;ESIMS m/z 181(([M+H]+))。
步骤3b:
向乙基溴化镁(EtMgBr;3.99mL,4mmol,1M在THF中)在THF的-78℃溶液中添加粗制(R)-3-甲基-2-苯氧基丁醛(~2mmol)在THF(6mL)的溶液,将混合物搅拌,直到TLC显示醛完全消耗。将反应混合物用饱和水溶液NH4Cl小心淬灭,用Et2O稀释,将各相分离。将水相用Et2O萃取,将合并的有机相用Na2SO4干燥,过滤,并浓缩。将粗制残余物通过快速柱色谱纯化(SiO2,0→10%丙酮在己烷中),得到作为无色油状物的标题化合物(187mg,45%):1H NMR(400MHz,CDCl3)δ7.29-7.22(m,2H),7.00-6.96(m,2H),6.95-6.89(m,1H),4.11(t,J=5.3Hz,1H),3.80-3.71(m,1H),2.15-2.03(m,1H),1.76-1.64(m,1H),1.57(d,J=4.5Hz,1H),1.49(ddd,J=14.3,9.6,7.2Hz,1H),1.02(d,J=6.8Hz,3H),1.01(t,J=7.5Hz,3H),0.97(d,J=6.9Hz,3H);13C NMR(101MHz,CDCl3)δ160.03,129.50,120.80,116.01,85.65,73.83,29.86,25.33,19.88,18.19,10.36;EIMS m/z 208。
实施例11,步骤1:制备(R)-3-甲基-2-苯氧基丁酸甲酯。
向(S)-2,2-二甲基-4-((R)-2-甲基-1-苯氧基丙基)-1,3-二氧戊环(1.45g,5.79mmol)在CH3CN(17mL)、四氯化碳(CCl4;17mL)和H2O(25mL)的混合物的溶液中添加原高碘酸(H5IO6;6.60g,29.0mmol),将所得无色混合物剧烈搅拌26h,用氯化钌(III)(RuCl3;0.024g,0.12mmol)处理,并剧烈搅拌80min。将反应混合物冷却至0℃,通过添加NaHSO3饱和水溶液(100mL)将其淬灭,并用EtOAc(150mL)稀释。将各相分离,将有机相用盐水(100mL)洗涤,用MgSO4干燥,过滤,并浓缩成黄色油状物,将其溶解于MeOH(8mL)和苯(22mL)的混合物中。将所得溶液用三甲基甲硅烷基重氮甲烷(5.79mL,11.6mmol,2M在Et2O中)处理,将反应混合物在室温搅拌30min。将溶剂和挥发性组分蒸发,得到黄色油状物,将其通过快速柱色谱纯化(SiO2,1→4%乙酸乙酯在己烷中),得到作为无色油状物的标题化合物(671mg,56%):1H NMR(400MHz,CDCl3)δ7.33-7.19(m,2H),7.03-6.93(m,1H),6.93-6.81(m,2H),4.38(d,J=5.6Hz,1H),3.74(s,3H),2.41-2.19(m,1H),1.09(d,J=6.8Hz,3H),1.06(d,J=6.9Hz,3H);13C NMR(101MHz,CDCl3)δ171.91,158.23,129.54,121.49,115.07,81.63,51.99,31.71,18.62,17.85;ESIMS m/z 209(([M+H]+))。
实施例11,步骤2:制备(R)-2,4-二甲基-3-苯氧基戊-2-醇。
在0℃向(R)-3-甲基-2-苯氧基丁酸甲酯(671mg,3.22mmol)在无水Et2O(16mL)的溶液中添加甲基溴化镁(3.22mL,9.67mmol,3M在Et2O中),将烧瓶从冷却浴中取出并将其升温至室温。在2h之后,通过添加H2O(20mL)将反应混合物淬灭,用EtOAc(20mL)稀释,将混合物用2M HCl处理,直到混合物变为澄清和两相。将各相分离,将水相用EtOAc(2 x 20mL)萃取。将有机相合并,用MgSO4干燥,过滤,并蒸发,得到油状物,将其通过快速柱色谱纯化(SiO2,2→10%丙酮在己烷中),得到作为透明无色油状物的标题化合物(526mg,78%):1HNMR(400MHz,CDCl3)δ7.32-7.22(m,2H),7.03-6.95(m,2H),6.95-6.88(m,1H),4.05(d,J=3.4Hz,1H),2.17(s,1H),2.13(ddp,J=10.3,6.9,3.4Hz,1H),1.29(s,3H),1.26(s,3H),1.05(d,J=6.8Hz,3H),1.01(d,J=6.9Hz,3H);13C NMR(101MHz,CDCl3)δ160.53,129.52,120.78,115.80,87.85,73.82,29.86,27.90,25.53,22.79,17.62;ESIMS m/z 209(([M+H]+))。
实施例12A:制备(S)-2-((叔丁氧基羰基)氨基)丙酸(1R,2S)-1-环戊基-1-(环丙基甲氧基)-丙-2-基酯(化合物737)。
向(1R,2S)-1-环戊基-1-(环丙基甲氧基)丙-2-醇(160mg,0.807mmol)在CH2Cl2(4.0mL)的溶液中添加(S)-2-((叔丁氧基羰基)氨基)丙酸(Boc-Ala-OH;168mg,0.888mmol)和DMAP(9.86mg,0.081mmol),然后添加N1-((乙基亚氨基)亚甲基)-N3,N3-二甲基丙烷-1,3-二胺氢氯化物(EDC;309mg,1.61mmol),将反应混合物在室温搅拌过夜,然后浓缩,得到黄色油状物。将粗物质通过快速柱色谱纯化(SiO2,1→12%丙酮在己烷中),得到作为无色油状物的标题化合物(189mg,63%):IR(薄膜)3362,2951,2869,1714,1500,1451cm-1;1H NMR(500MHz,CDCl3)δ5.10-4.96(m,2H),4.34-4.22(m,1H),3.54(dd,J=9.8,7.0Hz,1H),3.30(dd,J=9.8,6.8Hz,1H),3.16(dd,J=8.4,2.5Hz,1H),1.95-1.81(m,3H),1.71-1.59(m,3H),1.57-1.49(m,3H),1.45(s,9H),1.38(d,J=7.2Hz,3H),1.26(d,J=6.6Hz,3H),1.12-1.01(m,1H),0.56-0.46(m,2H),0.24-0.17(m,2H);ESIMS m/z 370(([M+H]+))。
实施例12B:制备2-((叔丁氧基羰基)氨基)丙酸(R)-2,4-二甲基-3-苯氧基戊-2-基酯(化合物728)。
向(R)-2,4-二甲基-3-苯氧基戊-2-醇(480mg,2.30mmol)、DMAP(845mg,6.91mmol)、Sc(OTf)3(680mg,1.38mmol)、和Boc-Ala-OH(1.31g,6.91mmol)在CH2Cl2(23mL)的0℃溶液中添加N,N′-甲烷二亚基二(丙-2-胺)(DIC;1.12mL,7.26mmol),将反应混合物加热至回流并在回流温度搅拌8h,将其冷却至室温,并搅拌另外24h。将混合物过滤通过短柱,将滤液用0.1N HCl(30mL)洗涤,用Na2SO4干燥,过滤,并蒸发,得到作为无色油状物的标题化合物(219mg,24%),其为非对映异构体的1∶1混合物:1H NMR(400MHz,CDCl3),对于一种非对映异构体,δ7.33-7.17(m,2H),7.03-6.82(m,3H),4.86(s,1H),4.64(dd,J=16.5,4.4Hz,1H),4.20-3.90(m,1H),2.18-2.03(m,1H),1.59-1.51(m,6H),1.44(s,9H),1.17(t,J=6.9Hz,3H),1.06(dd,J=6.9,1.5Hz,3H),1.01(dd,J=6.8,1.6Hz,3H);13C NMR(101MHz,CDCl3),对于两种非对映异构体,δ172.48,172.34,160.23,160.18,155.11,155.04,129.47,129.46,120.69,120.63,115.70,115.64,86.67,86.45,84.13,83.93,79.61,79.57,49.94,49.85,29.60,29.54,28.34,28.33,23.56,23.42,22.59,22.56,22.45,22.38,18.37,18.31,18.30,18.25;ESIMS m/z 380(([M+H]+))。
实施例13,步骤1:制备(S)-2-((二叔丁氧基羰基)氨基)丙酸(2S,3R)-3-(苄氧基)己-5-烯-2-基酯(化合物34和化合物131)。
向(S)-2-((叔丁氧基羰基)氨基)-丙酸(2S,3R)-3-(苄氧基)己-5-烯-2-基酯(129.6mg,0.343mmol)在CH3CN(3.4mL)的溶液中添加DMAP(62.9mg,0.515mmol)和Boc2O(225mg,1.030mmol),将所得浅橙色反应混合物在室温搅拌过夜。将混合物用另外的DMAP(62.9mg,0.515mmol)和Boc2O(225mg,1.030mmol)处理,并在室温搅拌另外2h。将反应混合物浓缩成棕/红色油状物,将其通过快速柱色谱纯化(SiO2,0→20%EtOAc在己烷中),得到作为透明无色油状物的标题化合物(176.6mg,97%):IR(薄膜)2981,2940,1739,1696,1642,1455cm-1;1H NMR(400MHz,CDCl3)δ7.39-7.22(m,10H),5.90-5.75(m,1H),5.17-4.90(m,4H),4.68(d,J=11.5Hz,1H),4.53(d,J=11.4Hz,1H),3.58(ddd,J=7.5,5.3,3.3Hz,1H),2.39-2.18(m,2H),1.51(d,J=6.9Hz,3H),1.48(s,18H),1.27(d,J=6.5Hz,3H);ESIMSm/z 500(([M+Na]+))。
实施例13,步骤2:制备(S)-2-((二叔丁氧基羰基)氨基)丙酸(2S,3R)-3-(苄氧基)-5-羟基戊-2-基酯(SM:化合物131)。
向(S)-2-((二叔丁氧基羰基)-氨基)丙酸(2S,3R)-3-(苄氧基)己-5-烯-2-基酯(154.6mg,0.324mmol)和NaHCO3(2.72mg,0.032mmol)在无水CH2Cl2(3.1mL)和无水MeOH(99μL)的混合物的溶液中添加5滴1%苏丹III在CH2Cl2的溶液。将反应混合物冷却至-78℃,将O3鼓泡通过溶液,直到其变为澄清和无色。将混合物用O2吹洗几分钟,用N2吹洗几分钟,用另外的MeOH(1.2mL)吸收,用单一部分的NaBH4(36.7mg,0.971mmol)处理,在搅拌下经历一夜将所得溶液升温至室温。通过添加H2O(20mL)将反应混合物淬灭,将各相分离。将水相用CH2Cl2(3 x 20mL)萃取,通过使合并的有机相穿过相分离器滤芯并蒸发成油状物而将其干燥,将其通过快速柱色谱纯化(SiO2,0→100%EtOAc在己烷中),得到作为透明无色油状物的标题化合物(132.6mg,81%):IR(薄膜)2981,1734,1694,1455cm-1;1H NMR(400MHz,CDCl3)δ7.39-7.27(m,5H),5.10(qd,J=6.5,2.5Hz,1H),4.98(q,J=6.9Hz,1H),4.77(d,J=11.3Hz,1H),4.50(d,J=11.3Hz,1H),3.81-3.63(m,3H),2.09(t,J=5.4Hz,1H),1.82-1.62(m,2H),1.52(d,J=7.0Hz,3H),1.48(s,18H),1.27(d,J=6.5Hz,3H);HRMS-ESI(m/z)(([M+Na]+)),对于C25H39NNaO8,计算值为504.2568;实测值为504.2567。
实施例13,步骤3:制备(S)-2-((二叔丁氧基羰基)氨基)丙酸(2S,3R)-3-(苄氧基)-5-甲氧基戊-2-基酯(产物:化合物132)。
向(S)-2-((二叔丁氧基羰基)-氨基)丙酸(2S,3R)-3-(苄氧基)-5-羟基戊-2-基酯(133mg,0.275mmol)在CH2Cl2(2.76mL)的溶液中添加Proton (118mg,0.551mmol)和三甲基氧鎓四氟硼酸盐(52.9mg,0.358mmol),将所得无色反应混合物在室温搅拌过夜。通过添加NaHCO3饱和水溶液(20mL)将所得混浊橙色的混合物小心淬灭,将各相分离。将水相用CH2Cl2(3 x 20mL)萃取,将合并的有机相依次用1N HCl水溶液(2 x 20mL)和盐水洗涤,通过使其穿过相分离器滤芯而将其干燥,将其蒸发,得到油状物,将其通过快速柱色谱纯化(SiO2,0→50%EtOAc在己烷中),得到作为透明无色油状物的标题化合物(113mg,79%):IR(薄膜)2980,2936,1739,1696,1455cm-1;1H NMR(400MHz,CDCl3)δ7.41-7.20(m,5H),5.07(qd,J=6.5,2.6Hz,1H),4.97(q,J=6.9Hz,1H),4.73(d,J=11.3Hz,1H),4.46(d,J=11.3Hz,1H),3.69(ddd,J=8.7,4.3,2.6Hz,1H),3.52-3.39(m,2H),3.28(s,3H),1.80-1.65(m,2H),1.52(d,J=6.9Hz,3H),1.48(s,18H),1.25(d,J=6.5Hz,3H);HRMS-ESI(m/z)([M+Na]+),对于C26H41NNaO8,计算值为518.2724;实测值为518.2718。
实施例14A,步骤1和2:制备(S)-2-(3-羟基-4-甲氧基吡啶甲酰胺基)丙酸(1R,2S)-1-环戊基-1-(环丙基-甲氧基)丙-2-基酯(化合物737,化合物786,和化合物845)。
步骤1:
向(S)-2-((叔丁氧基羰基)氨基)丙酸(1R,2S)-1-环戊基-1-(环丙基甲氧基)丙-2-基酯(189mg,0.512mmol)在CH2Cl2(3.4mL)的溶液中添加4N HCl在二氧杂环己烷的溶液(2.6mL,10.2mmol),将混合物在室温搅拌3h。将溶剂在N2流下蒸发,得到作为白色固体的中间体胺氢氯化物,(S)-1-(((1R,2S)-1-环戊基-1-(环丙基甲氧基)丙-2-基)氧基)-1-氧代丙-2-铵氯化物:ESIMS m/z 340([M+H]+)。
步骤2:
向(S)-1-(((1R,2S)-1-环戊基-1-(环丙基甲氧基)丙-2-基)氧基)-1-氧代丙-2-铵氯化物和3-羟基-4-甲氧基吡啶甲酸(95.0mg,0.563mmol)在CH2Cl2(3.4mL)的溶液中添加N-乙基-N-异丙基丙-2-胺(294μL,1.69mmol)和PyBOP(293mg,0.563mmol),将反应混合物在室温搅拌4h。将溶剂蒸发,将粗制油状物通过快速柱色谱纯化(SiO2,1→50%丙酮在己烷中),得到作为白色固体的标题化合物(118mg,55%):1H NMR(300MHz,CDCl3)δ12.13(d,J=0.6Hz,1H),8.47(d,J=7.9Hz,1H),7.99(d,J=5.2Hz,1H),6.88(dd,J=5.3,0.6Hz,1H),5.09(qd,J=6.5,2.3Hz,1H),4.78-4.66(m,1H),3.95(s,3H),3.51(dd,J=9.8,6.9Hz,1H),3.23(dd,J=9.9,6.8Hz,1H),3.17(dd,J=8.5,2.3Hz,1H),2.01-1.72(m,2H),1.75-1.45(m,6H),1.56(d,J=7.2Hz,3H),1.46-1.29(m,1H),1.28(d,J=6.6Hz,3H),1.11-0.96(m,1H),0.55-0.41(m,2H),0.15-0.06(m,2H);13C NMR(101MHz,CDCl3)δ171.45,168.69,155.40,148.77,140.50,130.42,109.46,85.27,77.27,75.19,56.09,48.12,42.50,30.03,29.15,25.44,25.11,18.21,13.72,11.11,2.87,2.84;HRMS-ESI(m/z)([M+H]+),对于C22H33N2O6,计算值为421.2333;实测值为421.2331。
实施例14B,步骤1和2:制备(S)-2-(3-羟基)-4-甲氧基吡啶甲酰胺基)丙酸(2S,3R)-3-(苄氧基)己-5-烯-2-基酯(化合物34,化合物180和化合物333)。
步骤1:
历时30秒向(S)-2-((叔丁氧基羰基)-氨基)丙酸(2S,3R)-3-(苄氧基)己-5-烯-2-基酯(182mg,0.483mmol)在CH2Cl2(1.6mL)的0℃溶液中逐滴添加2,2,2-三氟乙酸(TFA;400μL,5.19mmol),将所得橙色混合物升温至室温并在室温搅拌2h。将反应混合物用CH2Cl2(5mL)稀释,用饱和水溶液NaHCO3(5mL)洗涤,将各相分离。将水相用CH2Cl2(3 x 5mL)萃取,通过使合并的有机层穿过相分离器滤芯而将其干燥,并将其浓缩,得到作为澄清的无色油状物的中间体胺,(S)-2-氨基丙酸(2S,3R)-3-(苄氧基)己-5-烯-2-基酯(135mg,100%),其直接用于下一步骤:HRMS-ESI(m/z)([M+H]+),对于C16H24NO3,计算值为278.1751;实测值为278.1752。
步骤2:
历时45秒(sec)的时间段向(S)-2-氨基丙酸(2S,3R)-3-(苄氧基)己-5-烯-2-基酯(135mg,0.487mmol)、3-羟基-4-甲氧基吡啶甲酸(99mg,0.584mmol)、和PYBOP(304mg,0.584mmol)在CH2Cl2(4.87mL)的溶液中逐滴添加N-乙基-N-异丙基丙-2-胺(305μL,1.75mmol),将反应混合物在室温搅拌过夜。将混合物浓缩,将所得橙/棕色油状物通过快速柱色谱纯化(SiO2,0→50%丙酮在己烷中),得到作为透明无色油状物的标题化合物(212mg,86%):IR(薄膜)3369,3063,2981,2940,2877,1737,1648,1576,1528,1481,1452,1438cm-1;1H NMR(400MHz,CDCl3)δ12.12(d,J=0.6Hz,1H),8.49(d,J=7.9Hz,1H),7.94(d,J=5.2Hz,1H),7.38-7.19(m,5H),6.83(dd,J=5.2,2.6Hz,1H),5.84(ddt,J=17.2,10.2,7.0Hz,1H),5.20-5.00(m,3H),4.79-4.66(m,1H),4.62(d,J=11.5Hz,1H),4.52(d,J=11.5Hz,1H),3.92(s,3H),3.57(ddd,J=7.2,5.3,3.5Hz,1H),2.42-2.24(m,2H),1.54(d,J=7.2Hz,3H),1.31(d,J=6.5Hz,3H);HRMS-ESI(m/z)([M+H]+),对于C23H29N2O6,计算值为429.2020;实测值为429.2025。
实施例14C,步骤1和2:制备(S)-2-(3-羟基-4-甲氧基吡啶甲酰胺基)丙酸(2S,3R,4R)-4-苄基-3-异丁氧基己-2-基酯(化合物4,化合物146,和化合物293)。
步骤1:
向(S)-2-((((9H-芴-9-基)甲氧基)-羰基)氨基)丙酸(2S,3R,4R)-4-苄基-3-异丁氧基己-2-基酯(350mg,0.63mmol)在THF(6mL)的溶液中添加吗啉(0.63mL,7.2mmol),将所得溶液在室温搅拌4d。将混合物过滤,将滤液蒸发,得到粘性白色固体,将其通过反相柱色谱纯化(C18,CH3CN在H2O中,NaOAc缓冲液),得到中间体铵乙酸盐,即1-(((2S,3R,4R)-4-苄基-3-异丁氧基己-2-基)氧基)-1-氧代丙-2-铵乙酸盐。将该铵乙酸盐溶解于EtOAc(10mL),用饱和水溶液NaHCO3洗涤,将各相分离。将有机相用Na2SO4干燥,过滤,并浓缩,得到作为无色油状物的中间体胺,2-氨基丙酸(2S,3R,4R)-4-苄基-3-异丁氧基己-2-基酯(90mg,43%,在具胺碳处的非对映异构体的1.5∶1混合物):1H NMR(400MHz,CDCl3),对于两种非对映异构体,δ7.31-7.22(m,2H),7.21-7.12(m,3H),5.22-5.09(m,1H),3.52(adq,J=8.9,7.0Hz,1H),3.42(atd,J=8.5,6.4Hz,1H),3.30(at,J=4.9Hz,1H),3.24(addd,J=8.4,6.4,4.3Hz,1H),2.98(adt,J=13.8,3.8Hz,1H),2.43(addd,J=13.6,9.9,2.6Hz,1H),1.92-1.81(m,1H),1.72(adp,J=15.7,5.1Hz,1H),1.58(bs,2H),1.40-1.24(m,2H),1.34(ad,J=7.0Hz,3H),1.31-1.27(m,3H),0.94(ad,J=6.7Hz,6H),0.87(atd,J=7.5,3.1Hz,3H)。
步骤2:
向2-氨基丙酸(2S,3R,4R)-4-苄基-3-异丁氧基己-2-基酯(0.09g,0.268mmol)、3-羟基-4-甲氧基吡啶甲酸(0.05g,0.295mmol)、和PYBOP(0.209g,0.402mmol)在CH2Cl2(1.5mL)的悬浮液中添加N-乙基-N-异丙基丙-2-胺(0.141mL,0.805mmol),将所得深棕色溶液在室温搅拌48h,将反应混合物在EtOAc和1N HCl水溶液之间分配,将各相分离。将有机相用NaHCO3饱和水溶液洗涤,用Na2SO4干燥,过滤,并浓缩。将所得粗制残余物通过快速柱色谱纯化(SiO2,30%EtOAc在己烷中),得到作为无色油状物的标题化合物(125mg,96%),其为非对映异构体(在具胺碳处)的1.5∶1混合物:1H NMR(400MHz,CDCl3),对于两种非对映异构体,δ12.15(add,J=11.4,0.5Hz,1H),8.49(at,J=8.0Hz,1H),7.97(add,J=5.2,3.5Hz,1H),7.31-7.19(m,2H),7.15(m,3H),6.86(ad,J=5.1Hz,1H),5.25-5.16(m,1H),4.76-4.66(m,1H),3.94(s,3H),3.42(add,J=8.5,6.4Hz,1H),3.33(aq,J=5.0Hz,1H),3.22(addd,J=17.7,8.5,6.4Hz,1H),2.97(add,J=13.8,4.3Hz,1H),2.42(addd,J=13.6,10.0,3.2Hz,1H),1.89-1.77(m,1H),1.73(apptt,J=10.2,4.8Hz,1H),1.56(d,J=7.2Hz,3H),1.39-1.25(m,2H),1.37-1.22(m,3H),0.96-0.81(m,9H);13C NMR(101MHz,CDCl3),对于两种非对映异构体,δ171.51,171.44,168.76,168.70,155.38,155.37,148.77,141.54,141.53,140.50,130.43,129.14,128.19,128.17,125.66,125.64,109.46,81.72,79.54,79.50,73.20,73.19,56.08,48.10,48.01,43.62,43.55,35.39,29.20,22.18,22.00,19.51,19.46,18.32,18.23,15.54,15.30,10.82,10.63;ESIMS m/z 487(([M+H]+))。
实施例14D,步骤1和2:制备2-(3-羟基-4-甲氧基吡啶甲酰胺基)丙酸(R)-2,4-二甲基-3-苯氧基戊-2-基酯(化合物728,化合物779,和化合物835)。
步骤1:
向2-((叔丁氧基羰基)氨基)丙酸(R)-2,4-二甲基-3-苯氧基戊-2-基酯(197mg,0.519mmol)在无水CH2Cl2(5mL)的溶液中添加2,6-二甲基吡啶(302μL,2.60mmol)、然后添加三氟甲磺酸三甲基甲硅烷基酯(281μL,1.56mmol),将所得溶液在室温搅拌4h。将反应混合物用MeOH(2.5mL)稀释,将所得溶液在室温搅拌30min并浓缩,得到作为黄色油状物的中间体胺盐,即2-氨基丙酸(R)-2,4-二甲基-3-苯氧基戊-2-基酯三氟甲磺酸盐(223mg,100%):ESIMS m/z 280.4(([M+H]+))。
步骤2:
向2-氨基丙酸(R)-2,4-二甲基-3-苯氧基戊-2-基酯三氟甲磺酸盐(223mg,0.519mmol)在无水CH2Cl2(5mL)的溶液中添加3-羟基-4-甲氧基吡啶甲酸(97mg,0.57mmol)、PyBOP(297mg,0.571mmol)、和Hunig碱(299μL,1.71mmol),将所得混合物在室温搅拌2h,浓缩,将残余物通过柱色谱纯化(SiO2;4→40%丙酮在己烷中),得到作为油状物的标题化合物(24mg,11%):1H NMR(400MHz,CDCl3)δ12.18(d,J=3.7Hz,1H),8.40(d,J=7.6Hz,1H),7.99(d,J=5.0Hz,1H),7.26-7.17(m,2H),6.96(dd,J=7.8,4.9Hz,2H),6.92-6.80(m,2H),4.67(dd,J=19.2,4.4Hz,1H),4.47(dp,J=29.2,7.2Hz,1H),3.94(s,3H),2.12(ddt,J=13.8,6.9,3.3Hz,1H),1.62-1.54(m,6H),1.38-1.31(m,3H),1.06(dd,J=6.9,2.2Hz,3H),1.01(d,J=6.8Hz,3H);13C NMR(101MHz,CDCl3)δ171.32,171.28,168.62,168.55,160.11,155.36,148.73,148.71,140.47,130.55,129.48,120.75,120.66,115.72,115.58,109.41,87.27,86.97,84.10,83.64,56.07,48.53,48.44,29.71,29.60,23.77,23.46,22.65,22.43,22.29,18.33,18.26,18.01,17.92;HRMS-ESI(m/z)([M+H]+),对于C23H31N2O6,计算值为431.2177;实测值为431.2187。
实施例15:制备(S)-2-(3-羟基-4-甲氧基吡啶甲酰胺基)丙酸(1R,2S)-1-环戊基-1-(对甲苯基氧基)丙-2-基酯(化合物843和化合物846)。
将(S)-2-(3-羟基-4-甲氧基吡啶甲酰胺基)丙酸(1R,2S)-1-(2-氯-4-甲基苯氧基)-1-环戊基丙-2-基酯(202mg,0.411mmol)、5%Pd/C(88mg,0.041mmol)、和NEt3(172μL,1.234mmol)在EtOH(8.2mL)中的悬浮液在约1Atm(气球)的H2下在室温搅拌72h。将反应混合物过滤通过短柱,将滤液浓缩,得到油状物,将其通过快速柱色谱纯化(SiO2,1→30%丙酮在己烷中),得到作为泡沫状物的标题化合物(166mg,88%):1H NMR(400MHz,CDCl3)δ12.11(d,J=0.6Hz,1H),8.38(d,J=8.1Hz,1H),7.96(d,J=5.2Hz,1H),7.01-6.96(m,2H),6.86(d,J=5.4Hz,1H),6.81(d,J=8.5Hz,2H),5.15(qd,J=6.5,3.0Hz,1H),4.64-4.49(m,1H),4.28(dd,J=8.2,3.0Hz,1H),3.94(s,3H),2.24(s,3H),2.18-2.04(m,1H),1.91-1.78(m,1H),1.78-1.64(m,2H),1.62-1.40(m,5H),1.37(d,J=6.5Hz,3H),1.24(d,J=7.3Hz,3H);13C NMR(101MHz,CDCl3)δ171.62,168.64,157.82,155.35,148.73,140.43,130.46,130.34,129.84,116.30,109.40,83.42,74.16,56.07,47.99,42.21,29.65,29.01,25.43,25.10,20.44,17.67,14.26;HRMS-ESI(m/z)([M+H]+),对于C25H33N2O6,计算值为457.2333;实测值为457.2335。
实施例16A:制备(S)-2-(3-乙酰氧基-4-甲氧基吡啶甲酰胺基)丙酸(1R,2S)-1-(3-氯苯氧基)-1-环戊基丙-2-基酯(化合物841和化合物920)。
在室温向(S)-2-(3-羟基-4-甲氧基吡啶甲酰胺基)丙酸(1R,2S)-1-(3-氯苯氧基)-1-环戊基丙-2-基酯(100mg,0.210mmol)、NEt3(58.1μL,0.419mmol)、和DMAP(5.12mg,0.042mmol)在CH2Cl2(2.1mL)的溶液中添加乙酰氯(22.4μL,0.314mmol),将反应混合物搅拌过夜。将溶剂蒸发,将所得粗制油状物通过快速柱色谱纯化(SiO2,1→40%丙酮在己烷中),得到作为无色油状物的标题化合物(76mg,70%):1H NMR(500MHz,CDCl3)δ8.42(d,J=8.0Hz,1H),8.30(d,J=5.4Hz,1H),7.10(t,J=8.2Hz,1H),7.01-6.96(m,1H),6.93(t,J=2.2Hz,1H),6.85(ddd,J=7.9,1.9,0.9Hz,1H),6.80(ddd,J=8.4,2.5,0.9Hz,1H),5.13(qd,J=6.5,2.9Hz,1H),4.63-4.54(m,1H),4.31(dd,J=8.4,3.0Hz,1H),3.91(s,3H),2.39(s,3H),2.16-2.09(m,1H),1.82(td,J=10.1,7.6,4.9Hz,1H),1.73(qd,J=7.5,3.4Hz,1H),1.69-1.46(m,5H),1.43-1.36(m,1H),1.34(d,J=6.5Hz,3H),1.25(d,J=7.2Hz,3H);13C NMR(126MHz,CDCl3)δ172.16,168.91,162.37,160.58,159.44,146.65,141.43,137.49,134.72,130.20,121.15,116.75,114.47,109.73,83.60,73.66,56.29,47.97,42.12,29.70,28.93,25.40,25.07,20.75,18.01,14.10;HRMS-ESI(m/z)([M+H]+),对于C26H32ClN2O7,计算值为519.1893;实测值为519.1888。
实施例16B:制备(S)-2-(3-(乙酰氧基甲氧基)-4-甲氧基吡啶甲酰胺基)丙酸(1R,2S)-1-(3-氯苯氧基)-1-环戊基丙-2-基酯(化合物841和化合物911)。
在室温向(S)-2-(3-羟基-4-甲氧基吡啶甲酰胺基)丙酸(1R,2S)-1-(3-氯苯氧基)-1-环戊基丙-2-基酯(100mg,0.210mmol)和K2CO3(58.0mg,0.419mmol)在丙酮(2.1mL)的悬浮液中添加乙酸溴甲基酯(28.8μL,0.294mmol),将混合物加热至55℃并在55℃搅拌3h,冷却至室温,并搅拌过夜。将溶剂蒸发,将所得粗物质通过快速柱色谱纯化(SiO2,1→40%丙酮在己烷中),得到作为无色油状物的标题化合物(53.9mg,47%):1H NMR(500MHz,CDCl3)δ8.29-8.20(m,2H),7.11(t,J=8.1Hz,1H),6.95-6.91(m,2H),6.86(ddd,J=8.0,2.0,0.9Hz,1H),6.81(ddd,J=8.4,2.5,0.9Hz,1H),5.73(s,2H),5.17-5.10(m,1H),4.64-4.55(m,1H),4.32(dd,J=8.4,3.0Hz,1H),3.91(s,3H),2.17-2.09(m,1H),2.07(s,3H),1.87-1.79(m,1H),1.78-1.70(m,1H),1.70-1.64(m,1H),1.57(s,4H),1.42-1.36(m,1H),1.36(d,J=6.6Hz,3H),1.26(d,J=7.1Hz,3H);13C NMR(126MHz,CDCl3)δ172.25,170.29,162.95,160.59,160.27,145.68,144.04,142.35,134.72,130.19,121.15,116.73,114.53,109.53,89.58,83.63,73.63,56.17,48.18,42.12,29.71,28.91,25.39,25.05,20.87,17.84,14.10;HRMS-ESI(m/z)([M+H]+),对于C27H34ClN2O8,计算值为549.1998;实测值为549.1997。
实施例16C:制备(S)-2-(3-((2-乙氧基乙酰氧基)甲氧基)-4-甲氧基吡啶甲酰胺基)丙酸(2S,3S,4S)-4-苯氧基-3-丙氧基己-2-基酯(化合物326和化合物512)。
向(S)-2-(3-羟基-4-甲氧基吡啶甲酰胺基)丙酸(2S,3S,4S)-4-苯氧基-3-丙氧基己-2-基酯(103mg,0.217mmol)在丙酮(2mL)的溶液中添加Na2CO3(46.0mg,0.434mmol)、碘化钠(NaI;6.5mg,0.043mmol)和2-乙氧基乙酸氯甲基酯(49.7mg,0.326mmol),将混合物升温至40℃并在40℃搅拌6h,冷却至室温,并浓缩。将所得残余物通过快速柱色谱纯化(SiO2,2→30%丙酮在己烷中),得到作为无色油状物的标题化合物(41.4mg,32%):IR(薄膜)3383,2973,2936,2878,1774,1737,1677cm-1;1H NMR(400MHz,CDCl3)δ8.33(d,J=7.8Hz,1H),8.26(d,J=5.4Hz,1H),7.29-7.19(m,2H),6.98-6.89(m,4H),5.82(d,J=1.0Hz,2H),5.16(qd,J=6.4,4.2Hz,1H),4.72-4.63(m,1H),4.27-4.17(m,1H),4.10(s,2H),3.90(s,3H),3.65-3.47(m,5H),1.88-1.76(m,1H),1.75-1.65(m,1H),1.59-1.49(m,2H),1.42(d,J=7.2Hz,3H),1.36(d,J=6.4Hz,3H),1.23(t,J=7.0Hz,3H),1.00(t,J=7.4Hz,3H),0.87(t,J=7.4Hz,3H);HRMS-ESI(m/z)([M+H]+),对于C30H43N2O10,计算值为591.2912;实测值为591.2913。
实施例A:评价杀真菌活性:小麦斑枯病(wheat leaf blotch)(Zymoseptoriatritici;Bayer编码SEPTTR)):
将各技术级别的原料溶解于丙酮,将其接着与9体积的含110ppm Triton X-100的水混合。使用自动隔间喷雾器将杀真菌剂溶液施用于小麦幼苗,直至流失(run-off)。对所有受喷洒的植物进行空气干燥然后进一步处理。使用上述方法评价所有抗真菌剂针对所有目标病害的活性,除非另有规定。使用追踪喷雾施用法(track spray applications)还评价了小麦斑枯病和褐锈病活性,在此情况下将所述杀真菌剂调配为EC制剂,其在喷雾溶液中含0.1%Trycol 5941。
在温室中,使小麦植物(Yuma品种)在50%矿质土壤/50%无土Metro混合物中从种子开始生长直到第一片叶完全形成,每罐(pot)7-10株幼苗。在杀真菌剂处理之前或之后,用Zymoseptoria tritici芽孢水性悬浮液接种这些植物。接种之后,将植物保持在100%相对湿度(黑暗露水室中保持一天,然后在20℃有光照的露水室中保持两到三天),以使芽孢发芽和感染叶片。将植物接着转移至设置为20℃的温室,使病害发展。当病害症状完全表现于未处理植物的第一片叶片时,基于0%至100%的病害严重度分级,评价感染程度。使用对于处理的植物相对于未处理的植物的病害严重度之比计算病害防治百分比。
实施例B:评价杀真菌活性:小麦褐锈病(小麦叶锈菌(Puccinia triticina);同义词:Puccinia recondita f.sp.tritici;Bayer编码PUCCRT):
在温室中,使小麦植物(Yuma品种)在50%矿质土壤/50%无土Metro混合物中从种子开始生长直到第一片叶完全形成,每罐7-10株幼苗。在用杀真菌剂处理之前或之后,用小麦叶锈菌的芽孢水性悬浮液接种这些植物。接种之后,将植物保持在黑暗露水室,在22℃、100%相对湿度过夜,以使芽孢发芽和感染叶片。将植物接着转移至设置为24℃的温室,使病害发展。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用和病害评估。
实施例C:评价杀真菌活性:小麦颖枯病(小麦颖枯病菌(Leptosphaerianodorum);Bayer编码LEPTNO):
在温室中,使小麦植物(Yuma品种)在50%矿质土壤/50%无土Metro混合物中从种子开始生长直到第一片叶完全形成,每罐7-10株幼苗。在用杀真菌剂处理之后24小时,用小麦颖枯病菌的芽孢水性悬浮液接种这些植物。接种之后,将植物保持在100%相对湿度(黑暗露水室中保持一天,然后在20℃有光照的露水室中保持两天),以使芽孢发芽和感染叶片。将植物接着转移至设置为20℃的温室,使病害发展。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用和病害评估。
实施例D:评价杀真菌活性:苹果黑星病(苹果黑星病菌(Venturia inaequalis);Bayer编码VENTIN):
使苹果幼苗(McIntosh品种)生长于无土Metro混合物中,每罐一个植株。在试验中使用在顶部有两片展开的新叶的幼苗(剪掉植物底端的老叶)。在用杀真菌剂处理之后24小时,用苹果黑星病菌的芽孢悬浮液接种植物,并保持在22℃、100%相对湿度露水室中48小时,然后移到设置为20℃的温室,使病害发展。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用,以及对受喷洒的叶片进行病害评估。
实施例E:评价杀真菌活性:黄瓜白粉病(Erysiphe cichoracearum;Bayer编码ERYSCI):
使黄瓜幼苗(Bush Pickle品种)生长于无土Metro混合物中,每罐一个植株,且在12至14日龄时用于试验中。杀真菌剂处理后24小时用芽孢悬浮液接种植物。接种之后,将植物维持在设置为20℃的温室中直到病害完全表现。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用,以及对受喷洒的叶片进行病害评估。
实施例F:评价杀真菌活性:糖用甜菜褐斑病(Cercospora beticola;Bayer编码CERCBE):
使糖用甜菜植物(HH88品种)生长于无土Metro混合物中,并且有规律地修剪,使植株尺寸保持均匀,然后进行试验。在用杀真菌剂处理之后24小时用芽孢悬浮液接种植物。接种的植物保持在22℃露水室中48小时,接着在设置于24℃的底部通风的透明塑料罩温室中培育,直到病害症状完全表现。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用,以及对受喷洒的叶片进行病害评估。
实施例G:评价杀真菌活性:亚洲大豆锈病(豆薯层锈菌(Phakopsorapachyrhizi);Bayer编码PHAKPA):
将各技术级别的原料溶解于丙酮,接着将其与9体积的含0.011%吐温20的水混合。使用自动隔间喷雾器将杀真菌剂溶液施用于大豆幼苗,直至流失(run-off)。对所有受喷洒的植物进行空气干燥然后进一步处理。
大豆植物(Williams 82品种)生长于无土Metro混合物中,每罐一个植株。使用两周龄的幼苗进行试验。在用杀真菌剂处理之前3天接种植物或在用杀真菌剂处理之后1天接种植物。在黑暗露水室中在22℃和100%相对湿度培育植物24h,接着转移至23℃的生长室以使病害发展。评估受喷洒的叶片的病害严重度。
实施例H:评价杀真菌活性:大麦烫伤(Rhyncosporium secalis;Bayer编码RHYNSE):
使大麦幼苗(Harrington品种)繁殖于无土Metro混合物中,每罐有8至12株植物,且当第一片叶完成形成时用于试验中。在用杀真菌剂处理之后24小时通过Rhyncosporiumsecalis芽孢水性悬浮液来对接种植物进行试验。接种之后,在22℃、100%相对湿度将植物保持在露水室48小时。将植物接着转移至设置为20℃的温室,以使病害发展。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用,以及对受喷洒的叶片进行病害评估。
实施例I:评价杀真菌活性:稻瘟病(Pyricularia oryzae;Bayer编码PYRIOR):
使稻米幼苗(Japonica品种)繁殖于无土Metro混合物中,每罐有8至14株植物,且在12至14日龄时用于试验中。在用杀真菌剂处理之后24小时用Pyricularia oryzae芽孢水性悬浮液来对接种植物进行试验。接种之后,在22℃、100%相对湿度将植物保持在露水室48小时,以使芽孢发芽和感染叶片。将植物接着转移至设置为24℃的温室,以使病害发展。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用,以及对受喷洒的叶片进行病害评估。
实施例J:评价杀真菌活性:番茄早疫病(番茄早疫病菌(Alternaria solani);Bayer编码ALTESO):
使番茄植物(Outdoor girl品种)繁殖于无土Metro混合物中,每罐有一个植物,且在12至14日龄时用于试验中。在用杀真菌剂处理之后24小时用番茄早疫病菌芽孢水性悬浮液来对接种植物进行试验。接种之后,将植物在露水室中在22℃在100%相对湿度保持48h,以使芽孢发芽和感染叶片。将植物接着转移至22℃的生长室,以使病害发展。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用,以及对受喷洒的叶片进行病害评估。
实施例N:评价杀真菌活性:黄瓜炭疽病(Glomerella lagenarium;无性型:瓜类炭疽菌(Colletotrichum lagenarium);Bayer编码COLLLA):
使黄瓜幼苗(Bush Pickle品种)繁殖于无土Metro混合物中,每罐有一个植物,且在12至14日龄时用于试验中。在用杀真菌剂处理之后24小时用Glomerella lagenarium芽孢水性悬浮液对接种植物进行试验。接种之后,在22℃、100%相对湿度将植物保持在露水室48小时,以使芽孢发芽和感染叶片。将植物接着转移至设置为22℃的生长室,以使病害发展。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用,以及对受喷洒的叶片进行病害评估。
实施例K:评价杀真菌活性:黄瓜炭疽病(瓜类炭疽菌(Colletotrichumlagenarium);Bayer编码COLLLA):
使黄瓜幼苗(Bush Pickle品种)繁殖于无土Metro混合物中,每罐有一个植物,且在12至14日龄时用于试验中。在用杀真菌剂处理之后24小时用Glomerella lagenarium芽孢水性悬浮液对接种植物进行试验。接种之后,在22℃、100%相对湿度将植物保持在露水室48小时,以使芽孢发芽和感染叶片。将植物接着转移至设置为22℃的生长室,以使病害发展。遵循实施例A中描述的步骤进行杀真菌剂的配制、施用,以及对受喷洒的叶片进行病害评估。
表1.化合物结构、外观、和制备方法
*Cmpd No.-化合物编号
表2.分析数据
*Cmpd No.-化合物编号
表3.生物学测试的评级标准
表4.生物学活性-以高体积施用和低体积施用的PUCCRT和SEPTTR病害防治
*Cmpd No.-化合物编号
*LV-低体积
*HV-高体积
*PUCCRT-小麦褐锈病(Puccinia triticina)
*SEPTTR-小麦斑枯病(小麦叶斑病病原菌)
*1DP-施用保护剂1天
*3DC-治疗3天
*g/H-克每公顷
*ppm-份每百万份
表5.生物学活性-以100ppm的病害防治
*Cmpd No.-化合物编号
*ALTESO-番茄早疫病(番茄早疫病菌(Alternaria solani))
*CERCBE-糖用甜菜褐斑病(甜菜尾孢菌(Cercospora beticola))
*COLLLA-黄瓜炭疽病(瓜类炭疽菌(Colletotrichum lagenarium))
*ERYSCI-黄瓜白粉病(黄瓜白粉病(Erysiphe cichoracearum))
*1DP-施用保护剂1天
表6.生物学活性-以100ppm的病害防治
*Cmpd No.-化合物编号
*LEPTNO-小麦颖枯病(Leptosphaeria nodorum)
*PYRIOR-稻瘟病(Pyricularia oryzae)
*RHYNSE-大麦烫伤(Rhyncosporium secalis)
*VENTIN-苹果黑星病(苹果黑星病菌(Venturia inaequalis))
*1DP-施用保护剂1天
表7.生物学活性-以25ppm的病害防治
*Cmpd No.-化合物编号
*PHAKPA-亚洲大豆锈病(豆薯层锈菌(Phakopsora pachyrhizi))
*1DP-施用保护剂1天
*3DC-治疗3天
Claims (29)
1.式I化合物:
其中
X是H或C(O)R5;
Y是H,C(O)R5,或Q;
Q是
R1和R11独立地选自氢或脂族饱和烃基,其任选取代有0个、1个或多个R8;或者,R1和R11可以共同形成3-6元饱和或部分饱和的碳环或杂环,其任选取代有0个、1个或多个R8;
R2和R12独立地选自氢,脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8;
R3选自氢,C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8;
R4选自脂族饱和烃基,芳基,或酰基,它们各自任选取代有0个、1个或多个R8;
R5选自脂族饱和烃基氧基或苄氧基,它们各自任选取代有0个、1个或多个R8;
R6选自氢,脂族饱和烃基氧基,或卤素,它们各自任选取代有0个、1个或多个R8;
R7选自氢,-C(O)R9,或-CH2OC(O)R9;
R8选自氢,脂族饱和烃基,芳基,酰基,卤素,烯基,脂族饱和烃基氧基,或杂环基,它们各自任选取代有0个、1个或多个R10;
R9选自脂族饱和烃基,脂族饱和烃基氧基,或芳基,它们各自任选取代有0个、1个或多个R8;
R10选自氢,脂族饱和烃基,芳基,酰基,卤素,烯基,脂族饱和烃基氧基,或杂环基。
2.权利要求1的化合物,其中X和Y是氢。
3.权利要求2的化合物,其中R1和R11独立地选自氢或脂族饱和烃基。
4.权利要求2的化合物,其中R2和R12独立地选自氢或脂族饱和烃基。
5.权利要求2的化合物,其中R3选自C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8。
6.权利要求2的化合物,其中R4选自脂族饱和烃基或芳基,它们各自任选取代有0个、1个或多个R8。
7.权利要求2的化合物,其中R1和R11独立地选自氢或脂族饱和烃基;R2和R12独立地选自氢或脂族饱和烃基;R3选自C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8;R4选自脂族饱和烃基或芳基,它们各自任选取代有0个、1个或多个R8。
8.权利要求1的化合物,其中X是C(O)R5,Y是氢。
9.权利要求8的化合物,其中R1和R11独立地选自氢或脂族饱和烃基。
10.权利要求8的化合物,其中R2和R12独立地选自氢或脂族饱和烃基。
11.权利要求8的化合物,其中R3选自C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8。
12.权利要求8的化合物,其中R4选自脂族饱和烃基或芳基,它们各自任选取代有0个、1个或多个R8。
13.权利要求8的化合物,其中R1和R11独立地选自氢或脂族饱和烃基;R2和R12独立地选自氢或脂族饱和烃基;R3选自C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8;R4选自脂族饱和烃基或芳基,它们各自任选取代有0个、1个或多个R8。
14.权利要求1的化合物,其中X是氢,Y是Q。
15.权利要求14的化合物,其中R6是脂族饱和烃基氧基。
16.权利要求15的化合物,其中R7是氢。
17.权利要求16的化合物,其中R1和R11独立地选自氢或脂族饱和烃基。
18.权利要求16的化合物,其中R2和R12独立地选自氢或脂族饱和烃基。
19.权利要求16的化合物,其中R3选自C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8。
20.权利要求16的化合物,其中R4选自脂族饱和烃基或芳基,它们各自任选取代有0个、1个或多个R8。
21.权利要求16的化合物,其中R1和R11独立地选自氢或脂族饱和烃基;R2和R12独立地选自氢或脂族饱和烃基;R3选自C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8;R4选自脂族饱和烃基或芳基,它们各自任选取代有0个、1个或多个R8。
22.权利要求15的化合物,其中R7选自-C(O)R9,或-CH2OC(O)R9。
23.权利要求22的化合物,其中R9是脂族饱和烃基,其任选取代有0个、1个或多个R8。
24.权利要求23的化合物,其中R1和R11独立地选自氢或脂族饱和烃基。
25.权利要求23的化合物,其中R2和R12独立地选自氢或脂族饱和烃基。
26.权利要求23的化合物,其中R3选自脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8。
27.权利要求23的化合物,其中R4选自脂族饱和烃基或芳基,它们各自任选取代有0个、1个或多个R8。
28.权利要求23的化合物,其中R1和R11独立地选自氢或脂族饱和烃基;R2和R12独立地选自氢或脂族饱和烃基;R3选自C2-C6脂族饱和烃基,芳基,或烯基,它们各自任选取代有0个、1个或多个R8;R4选自脂族饱和烃基或芳基,它们各自任选取代有0个、1个或多个R8。
29.权利要求28的化合物,其中R9选自-CH3,-CH2OCH2CH3,-CH2CH2OCH3,-CH(CH3)2,-CH2CH2CH2CH3,-环丙基。
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