CN113173838A - 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
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- CN113173838A CN113173838A CN202110314842.4A CN202110314842A CN113173838A CN 113173838 A CN113173838 A CN 113173838A CN 202110314842 A CN202110314842 A CN 202110314842A CN 113173838 A CN113173838 A CN 113173838A
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- Prior art keywords
- compound
- methyl
- chloride
- compounds
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- 230000000855 fungicidal effect Effects 0.000 title abstract description 45
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 190
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 93
- 238000000034 method Methods 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical group Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 pyridine amides Chemical class 0.000 abstract description 64
- 239000000417 fungicide Substances 0.000 abstract description 43
- 241000233866 Fungi Species 0.000 abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 107
- 239000000203 mixture Substances 0.000 description 91
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 74
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 74
- 241000196324 Embryophyta Species 0.000 description 71
- 239000005944 Chlorpyrifos Substances 0.000 description 52
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 52
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 41
- 239000005822 Propiconazole Substances 0.000 description 39
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 39
- 229940050176 methyl chloride Drugs 0.000 description 37
- 201000010099 disease Diseases 0.000 description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 35
- 238000002360 preparation method Methods 0.000 description 33
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 description 31
- 238000009472 formulation Methods 0.000 description 31
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 29
- XKSAJZSJKURQRX-UHFFFAOYSA-N 2-acetyloxy-5-(4-fluorophenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC=C1C1=CC=C(F)C=C1 XKSAJZSJKURQRX-UHFFFAOYSA-N 0.000 description 28
- 239000005820 Prochloraz Substances 0.000 description 28
- 241000209140 Triticum Species 0.000 description 28
- 229950007979 flufenisal Drugs 0.000 description 28
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- 239000003921 oil Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 235000021307 Triticum Nutrition 0.000 description 25
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 24
- 238000003818 flash chromatography Methods 0.000 description 22
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 21
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 19
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 description 19
- 239000005869 Pyraclostrobin Substances 0.000 description 19
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 19
- 125000001931 aliphatic group Chemical group 0.000 description 18
- YWBVHLJPRPCRSD-UHFFFAOYSA-N Fluridone Chemical compound O=C1C(C=2C=C(C=CC=2)C(F)(F)F)=CN(C)C=C1C1=CC=CC=C1 YWBVHLJPRPCRSD-UHFFFAOYSA-N 0.000 description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 16
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 description 16
- 239000005939 Tefluthrin Substances 0.000 description 16
- 239000012230 colorless oil Substances 0.000 description 16
- 229930195734 saturated hydrocarbon Natural products 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 239000007832 Na2SO4 Substances 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- BYUKOOOZTSTOOH-UHFFFAOYSA-N 2-(2-sulfoethyldisulfanyl)ethanesulfonic acid Chemical compound OS(=O)(=O)CCSSCCS(O)(=O)=O BYUKOOOZTSTOOH-UHFFFAOYSA-N 0.000 description 12
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000005582 Metosulam Substances 0.000 description 12
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 description 12
- 229950009278 dimesna Drugs 0.000 description 12
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 11
- 229960004503 metoclopramide Drugs 0.000 description 11
- 239000000575 pesticide Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 10
- 240000005979 Hordeum vulgare Species 0.000 description 10
- 235000007340 Hordeum vulgare Nutrition 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- 239000005828 Pyrimethanil Substances 0.000 description 10
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 9
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 9
- 239000005506 Diclofop Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000007900 aqueous suspension Substances 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 238000004293 19F NMR spectroscopy Methods 0.000 description 8
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- URXNNPCNKVAQRA-XMHGGMMESA-N pyraoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C=2C=CC(Cl)=CC=2)=NN1C URXNNPCNKVAQRA-XMHGGMMESA-N 0.000 description 8
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- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 8
- 244000068988 Glycine max Species 0.000 description 7
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- 241000223259 Trichoderma Species 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 7
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 7
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
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- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 230000009885 systemic effect Effects 0.000 description 7
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- 241000220225 Malus Species 0.000 description 6
- 239000005916 Methomyl Substances 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229910021538 borax Inorganic materials 0.000 description 6
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 6
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 6
- 239000003880 polar aprotic solvent Substances 0.000 description 6
- ZBAFFZBKCMWUHM-UHFFFAOYSA-N propiram Chemical compound C=1C=CC=NC=1N(C(=O)CC)C(C)CN1CCCCC1 ZBAFFZBKCMWUHM-UHFFFAOYSA-N 0.000 description 6
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- 239000002169 Metam Substances 0.000 description 5
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- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 5
- 229960005286 carbaryl Drugs 0.000 description 5
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- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 5
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 5
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 5
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Classifications
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- C07C229/20—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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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。杀真菌剂为天然或合成来源的化合物,其用于保护和/或治愈植物抵抗由农业相关的真菌引起的损害。一般而言,单个的杀真菌剂不可能用于全部情形中。因此,一直从事研究制备可能具有更好的性能、更容易使用和成本更少的杀真菌剂。
Description
本申请是申请日为2015年12月18日、申请号为201580074495.5(国际申请号为PCT/US2015/066760)、名称为“具有杀真菌活性的吡啶酰胺化合物”的发明专利申请的分案申请。
相关申请的交叉引用
本申请要求了2014年12月30日提交的美国临时专利申请序列号62/098120和2014年12月30日提交的美国临时专利申请序列号62/098122的权益,将其明确并入本申请中以作参考。
背景技术和发明内容
杀真菌剂为天然或合成来源的化合物,其用于保护和/或治愈植物抵抗由农业相关的真菌引起的损害。通常,在所有情况下单一真菌剂均不是有用的。因此,正在研究制备杀真菌剂,其可以具有较好性能,较易于使用,以及成本较低。
本申请涉及吡啶酰胺(picolinamides)及它们作为杀真菌剂的用途。本申请的化合物可以提供抵抗子囊菌(ascomycetes),担子菌(basidiomycetes),半知菌(deuteromycetes),和卵菌(oomycetes)的保护。
本申请的一个实施方式可以包括式I化合物:
其中:
X为氢或C(O)R5;
Y为氢、C(O)R5或Q;
Q为
其中:
Z为N或CH;
R1为氢或脂族饱和烃基,各自取代有0、1或多个R8;
R2为甲基;
R3选自芳基或杂芳基,各自任选取代有0、1或多个R8;
R4选自氢、卤素、羟基、脂族饱和烃基或脂族饱和烃基氧基;
R5选自脂族饱和烃基氧基或苄氧基,各自任选取代有0、1或多个R8;
R6选自氢、脂族饱和烃基氧基或卤素,各自任选取代有0、1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、炔基、脂族饱和烃基氧基、氰基或杂环基,各自任选取代有0、1或多个R10;
R9选自脂族饱和烃基、脂族饱和烃基氧基或芳基,各自任选取代有0、1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;
R11选自氢或取代有0、1或多个R8的脂族饱和烃基;和
R12选自芳基或杂芳基,各自任选取代有0、1或多个R8。
本申请的其他实施方式可以包括用于控制或预防真菌侵袭的杀真菌组合物,其包含上述化合物和植物学上可接受的载体物质。
本申请的其他实施方式还可以包括用于控制或预防真菌对植物侵袭的方法,所述方法包括以下步骤:将杀真菌有效量的一种或多种上述化合物施用至真菌,植物,以及与植物相邻的区域中的至少之一。
本申请还包括以下实施方式:
实施方式1.式I的化合物
其中:
X为氢或C(O)R5;
Y为氢、C(O)R5或Q;
Q为
其中:
Z为N或CH;
R1为氢或取代有0、1或多个R8的脂族饱和烃基;
R2为甲基;
R3选自芳基或杂芳基,各自任选取代有0、1或多个R8;
R4选自氢、卤素、羟基、脂族饱和烃基或脂族饱和烃基氧基;
R5选自脂族饱和烃基氧基或苄氧基,各自任选取代有0、1或多个R8;
R6选自氢、脂族饱和烃基氧基或卤素,各自任选取代有0、1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、炔基、脂族饱和烃基氧基、氰基或杂环基,各自任选取代有0、1或多个R10;
R9选自脂族饱和烃基、脂族饱和烃基氧基或芳基,各自任选取代有0、1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;
R11选自氢或取代有0、1或多个R8的脂族饱和烃基;和
R12选自芳基或杂芳基,各自任选取代有0、1或多个R8。
实施方式2.根据实施方式1的化合物,其中X和Y为氢。
实施方式3.根据实施方式2的化合物,其中R1和R11独立地选自氢或脂族饱和烃基。
实施方式4.根据实施方式2的化合物,其中R3和R12独立地为芳基,各自任选取代有0、1或多个R8。
实施方式5.根据实施方式2的化合物,其中R4为H。
实施方式6.根据实施方式2的化合物,其中R1和R11独立地选自氢或脂族饱和烃基,R3和R12独立地为芳基,各自任选取代有0、1或多个R8,且R4为H。
实施方式7.根据实施方式1的化合物,其中X为C(O)R5且Y为氢。
实施方式8.根据实施方式7的化合物,其中R1和R11独立地选自氢或脂族饱和烃基。
实施方式9.根据实施方式7的化合物,其中R3和R12独立地为芳基,各自任选取代有0、1或多个R8。
实施方式10.根据实施方式7的化合物,其中R4为H。
实施方式11.根据实施方式7的化合物,其中R1和R11独立地选自氢或脂族饱和烃基,R3和R12独立地为芳基,各自任选取代有0、1或多个R8,且R4为H。
实施方式12.根据实施方式1的化合物,其中X为氢且Y为Q。
实施方式13.根据实施方式12的化合物,其中Z为N。
实施方式14.根据实施方式13的化合物,其中R6为脂族饱和烃基氧基。
实施方式15.根据实施方式14的化合物,其中R7为氢。
实施方式16.根据实施方式15的化合物,其中R1和R11独立地选自氢或脂族饱和烃基。
实施方式17.根据实施方式15的化合物,其中R3和R12独立地为芳基,各自任选取代有0、1或多个R8。
实施方式18.根据实施方式15的化合物,其中R4为H。
实施方式19.根据实施方式15的化合物,其中R1和R11独立地选自氢或脂族饱和烃基,R3和R12独立地为芳基,各自任选取代有0、1或多个R8,且R4为H。
实施方式20.根据实施方式14的化合物,其中R7选自-C(O)R9或-CH2OC(O)R9。
实施方式21.根据实施方式20的化合物,其中R1和R11独立地选自氢或脂族饱和烃基。
实施方式22.根据实施方式20的化合物,其中R3和R12独立地为芳基,各自任选取代有0、1或多个R8。
实施方式23.根据实施方式20的化合物,其中R4为H。
实施方式24.根据实施方式20的化合物,其中R1和R11独立地选自氢或脂族饱和烃基,R3和R12独立地为芳基,各自任选取代有0、1或多个R8,且R4为H。
实施方式25.根据实施方式24的化合物,其中R9选自-CH3-、-CH2OCH2CH3-、-CH2CH2OCH3-、-CH(CH3)2-、-CH2CH2CH2CH3-、-环丙基。
实施方式26.防治真菌病原体的组合物,其包括至少一种实施方式1的化合物和另一种农药的混合物,所述另一种农药包括杀真菌剂,杀虫剂,杀线虫剂,杀螨剂,杀节肢动物剂,杀细菌剂,以及它们的组合。
实施方式27.防治真菌病原体的组合物,其包括至少一种实施方式15的化合物和另一种农药的混合物,所述另一种农药包括杀真菌剂,杀虫剂,杀线虫剂,杀螨剂,杀节肢动物剂,杀细菌剂,以及它们的组合。
实施方式28.防治真菌病原体的组合物,其包括至少一种实施方式20的化合物和另一种农药的混合物,所述另一种农药包括杀真菌剂,杀虫剂,杀线虫剂,杀螨剂,杀节肢动物剂,杀细菌剂,以及它们的组合。
实施方式29.控制和预防真菌对植物侵袭的方法,所述方法包括以下步骤:将杀真菌有效量的至少一种实施方式1-25中任一项的化合物施用至以下的至少之一:所述植物,与所述植物相邻的区域,适于支持所述植物生长的土壤,所述植物的根,和所述植物的叶子。
实施方式30.控制和预防真菌对植物侵袭的方法,所述方法包括以下步骤:将杀真菌有效量的至少一种实施方式26-28中任一项的组合物施用至以下的至少之一:所述植物,与所述植物相邻的区域,适于支持所述植物生长的土壤,所述植物的根,和所述植物的叶子。
本领域技术人员将会理解的是,以下术语可以包括它们定义范围内的一般的"R"-基团,例如,"术语脂族饱和烃基氧基是指-OR取代基"。也应理解的是,在以下术语的定义范围内,包括这些"R"基团用于说明的目的,不应该解释为限制性的或受关于式I的取代基的限制。
术语"脂族饱和烃基"是指支化,非支化或饱和的环状碳链,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,非支化或环状碳链,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"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环或非芳环,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为选自列表1、2、3、4、5或6的整数。
术语"卤代脂族饱和烃基氧基"是-OR-X取代基,其中X为Cl、F、Br或I或其任意组合。
术语"卤代脂族饱和烃基"是指被Cl、F、I或Br或其任意组合取代的脂族饱和烃基。
术语"卤素"或"卤代"是指一个或多个卤素原子,定义为F、Cl、Br和I。
术语"硝基"是指–NO2取代基。
术语硫代脂族饱和烃基是指–SR取代基。
在本申请全文中,提及式I化合物也理解为包括所有的立体异构体,例如非对映异构体,对映异构体,及它们的混合物。在另一个实施方式中,式(I)也理解为包括它们的盐或水合物。示例性的盐包括但不限于:盐酸盐、氢溴酸盐、氢碘酸盐、三氟乙酸盐和三氟甲磺酸盐。
本领域技术人员也理解的是,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。
本申请的另一个实施方式为式I化合物的用途,用于保护植物免受致植物病原微生物侵袭或用于处理被致植物病原微生物侵害的植物,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。
另外,本申请的另一个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配,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,麸质,蒙脱土,硅藻土,精制硅酸盐等。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在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,和复杂的醇例如2-乙氧基乙醇。
本申请可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。用于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,和烷基和芳基酚、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,例如乙氧基化烷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。阴离子乳化剂包括烷基芳基磺酸的油溶盐(例如,钙盐),硫酸化聚二醇醚的油溶盐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;各种脂肪酸的二烷基酰胺,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,菜籽油,橄榄油,蓖麻油,葵化籽油,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;等等。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总重量计,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的式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,其浓度为约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构成,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,所述颗粒载体已经预先制成合适的粒度(范围为约0.5至约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粒状颗粒。
含有式I化合物的粉剂可以如下制备: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,所述载体例如高岭粘土,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,乙氧基化有机硅氧烷,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;苄基椰油烷基二甲基季铵盐;石油烃、烷基酯、有机酸和阴离子表面活性剂的共混物;C9-C11烷基聚糖苷;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;十三烷基醇(合成)乙氧基化物(8EO);牛油胺乙氧基化物(15EO);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序列号11/495,228中披露的那些,将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农药化合物的组合。所述额外的农药化合物可以是杀真菌剂,杀虫剂,除草剂,杀线虫剂,杀螨剂,杀节肢动物剂(arthropodicide),杀菌剂或它们的组合,所述额外的农药化合物在就施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,将所述其它农药化合物作为增补毒剂使用,用于相同或不同的农药用途。所述式I化合物和农药化合物通常可以1:100至100:1的重量比以组合的形式存在。
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其它杀真菌剂配制在一起,可与其它杀真菌剂罐混合在一起,或可与其它杀真菌剂相继施用。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-hydroxy quinoline 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-isopropyl),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(calcium polysulfide),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(Coniothyrium Minitans),氢氧化铜(copper hydroxide),辛酸酮(copper octanoate),王铜(copper oxychloride),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 freebase),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(guazatineacetates),四硫钠(GY-81),六氯苯(hexachloro苯),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(iminoctadinetriacetate),双胍辛胺三(对十二烷基苯磺酸盐)[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(mercurouschloride),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(methyl iodide),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(fatty acid)),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(pentachlorophenyllaurate),吡噻菌胺(penthiopyrad),乙酸苯汞(phenyl mercury 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(potassiumbicarbonate),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(propamocarb hydrochloride),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-dichlorophenyldichlorophenyl)-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-氯-2,4-dinitronaphthalene),1-氯-2-硝基丙烷(1-氯-2-nitropropane),2-(2-十七烷基-2-咪唑啉-1-基)乙醇(2-(2-heptadecyl-2-imidazolin-1-基)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-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-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-methoxyethylmercurysilicate),3-(4-氯苯基)-5-甲基绕丹宁(3-(4-chlorophenyl)-5-methylrhodanine),硫氰酸4-(2-硝基丙-1-烯基)苯酯(4-(2-nitroprop-1-enyl)phenyl thiocyanateme),氨丙膦酸(am丙基fos),敌菌灵(anilazine),氧化福美双(azithiram),多硫化钡(bariumpolysulfide),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 calciumcopper 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农药结合,包括杀昆虫剂、杀线虫剂、杀螨剂、杀节肢动物剂,杀细菌剂或它们的组合,所述其它农药在就施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可以与一种或多种其它农药联合施用,从而防治更宽范围的不期望害虫。当与其它农药联合施用时,本申请要求保护的化合物可与其它农药配制在一起,可与其它农药罐混合在一起,或可与其它农药相继施用。常见的杀昆虫剂包括但不限于: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(氨基carb),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-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(DNOC-ammonium),二硝甲酚-钾(DNOC-potassium),二硝甲酚-钠(DNOC-sodium),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(ethyl-DDD),1,2-二溴乙烷(ethylene dibromide),1,2-二氯乙烷(ethylenedichloride),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(gamma-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(juvenilehormone 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(methyl chloroform),二氯甲烷(methylenechloride),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(milbemycinoxime),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-dichloro苯),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(potassiumthiocyanate),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(pyrethrinI),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(sodium hexafluorosilicate),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(sulfurylfluoride),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(thiocyclam oxalate),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施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农药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除草剂配制在一起,可与除草剂罐混合在一起,或可与除草剂相继施用。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(氨基cyclopyrachlor),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(calcium chlorate),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),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控制或预防真菌侵袭的方法。该方法包括向土壤、植物、根、叶子、或真菌所在地或向要预防感染的所在地(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。
所述化合物具有宽范围的抵抗真菌病原体的活性。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 leaf blotch)(小麦叶斑病病原菌(Zymoseptoria tritici)),小麦褐锈病(wheat brown rust)(小麦叶锈菌(Pucciniatriticina)),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(Venturia inaequalis)),葡萄白粉病(powdery mildew of grapevine)(葡萄白粉病(Uncinula necator)),大麦烫伤(barleyscald)(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(Phakopsorapachyrhizi)),小麦颖枯病(glume blotch of wheat)(小麦颖枯病菌(Leptosphaerianodorum)),小麦白粉病(powdery mildew of wheat)(小麦白粉菌(Blumeria graminisf.sp.tritici)),大麦白粉病(powdery mildew of barley)(大麦白粉病菌(Blumeriagraminis f.sp.hordei)),瓜类白粉病(powdery mildew of cucurbits)(黄瓜白粉病(Erysiphe cichoracearum)),瓜类炭疽病(Anthracnose of cucurbits)(黄瓜炭疽病(Colletotrichum lagenarium)),甜菜褐斑病(leaf spot of beet)(甜菜尾孢菌(Cercospora beticola)),番茄早疫病(early blight of tomato)(番茄早疫病菌(Alternaria solani)),和大麦斑点病(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。在该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的化合物,其中R3和R12如最初所定义并且是等同的,可以通过方案1步骤a中所示的方法制备。式1.0的化合物可以在极性非质子溶剂如四氢呋喃(THF)中于约0℃至23℃的温度以有机金属亲核试剂如苯基溴化镁(PhMgBr)处理得到式1.1的化合物,其中R3和R12如之前所定义,如在a中所显示。
方案1
式2.2的化合物,其中R3如最初所定义并且可以与R12相同或不同,可以通过如方案2,步骤a–c中所示的方法制备。式2.2的化合物,其中R3和R12如之前所定义但不是缺电子的芳基或杂芳基且可以等同或不等同,可以通过在卤化溶剂如二氯甲烷(DCM)于约0℃至23℃的温度以氢化物试剂如三乙基甲硅烷(Et3SiH)和酸如2,2,2-三氟乙酸(TFA)的混合物处理式2.0的化合物(其中R3和R12如之前所定义但不是缺电子的芳基或杂芳基且可以等同或不等同)来得到,如a中所描述。或者,式2.1的化合物,其中R3和R12为缺电子的芳基或杂芳基且可以等同或不等同,可以通过在极性非质子溶剂如THF中于约23℃的温度以碱如氢化钠(NaH)和催化剂如咪唑处理式2.0的化合物(其中R3和R12为缺电子的芳基或杂芳基且可以等同或不等同),接着顺序添加二硫化碳(CS2)和脂族饱和烃基碘化物如碘甲烷(Mel)来得到,如b中所描绘。式2.2的化合物,其中R3和R12为缺电子的芳基或杂芳基且可以等同或不等同,可以通过在非极性溶剂如甲苯中于约115℃的温度以锡试剂如三丁基氢化锡和自由基引发剂如偶氮二异丁腈(AIBN)处理处理式2.1的化合物(其中R3和R12如之前所定义且可以相同或不同)来得到,如c中所描绘。
方案2
式3.1的化合物,其中R3和R12如最初所定义且可以相同或不同,可以根据方案3,步骤a中概述的方法制备。式3.1的化合物,其中R3和R12如最初所定义并且可以相同或不同,可以从式3.0的化合物(其中R3和R12如之前所定义并且可以相同或不同制备,通过以碱如NaH和脂族饱和烃基卤化物如MeI在极性非质子溶剂如N,N-二甲基甲酰胺(DMF)中于0℃至23℃的温度进行处理,如a中所描绘的。
方案3
式4.1的化合物,其中R3和R12如最初所定义并且可以等同或不同,可以根据方案4,步骤a中概述的方法制备。式4.1的化合物,其中R3和R12如最初所定义并且可以相同或不同,可以从式4.0的化合物(其中R3和R12如之前所定义并且可以相同或不同)制备,通过以氟化试剂如(二乙基氨基)三氟化硫(DAST)在卤化溶剂如DCM中于约0℃至23℃的温度进行处理,如在a中所描绘的。
方案4
式5.3的化合物,其中R3、R4和R12如最初所定义且R3可以与R12相同或不同,可以根据方案5,步骤a-c中所概述的方法制备。式5.3的化合物,其中R3、R4和R12如最初所定义且R3可以与R12相同或不同,可以从式5.0的化合物(其中R3、R4和R12如最初所定义且R3可以与R12相同或不同)制备,通过以催化剂如钯/碳(Pd/C)在不饱和烃溶剂如环己烯和极性质子溶剂如乙醇(EtOH)的混合物中于约65℃的升高的温度进行处理,如a中所示。或者式5.3的化合物,其中R3和R12为缺电子的芳基或杂芳基且可以相同或不同并且R4为羟基(OH)或脂族饱和烃基氧基,可以通过以氢化物试剂如Et3SiH和酸如TFA的混合物在卤化溶剂DCM中于约0℃至23℃的温度处理式5.1的化合物(其中R3、R4和R12如之前所定义且R3可以与R12相同或不同),如b中所指示的。此外,式5.3的化合物,其中R3和R12如最初所定义的但不是缺电子芳基或杂芳基且可以相同或不同并且R4为质子(H),可以通过以氢化物试剂Et3SiH和酸如TFA的混合物在卤化溶剂如DCM中于约0℃至23℃的温度处理式5.2的化合物(其中R3、R4和R12如之前所定义且R3可以与R12相同或不同)来得到,如c中所描述的。
方案5
式6.2的化合物,其中R3和R12为缺电子的芳基或杂芳基并且相同,可以根据方案6,步骤a–b中概述的方法制备。式6.1的化合物,其中R3和R12如之前所描述的,可以从式6.0的化合物制备,通过以芳基溴如4-溴苯基氰在Pd催化剂如XPhos Pd G3(CAS#1445085-55-1,从Sigma-Aldrich购得)的存在下在极性非质子溶剂如THF中于约55℃的温度进行处理,如a中所指示的。式6.2的化合物,其中R3和R12如之前所描述的,可以从式6.1的化合物(其中R3和R12如之前所描述)制备,通过以氢化物试剂如硼烷二甲基硫化物复合物在催化剂如(R)-(+)-2-甲基-CBS-噁唑硼烷的存在下在极性质子溶剂如甲醇(MeOH)中于约0℃的温度进行处理,如b中所指示的。
方案6
式7.2的化合物,其中R3和R12如最初所定义并且是等同的,可以根据方案7,步骤a–b中所概述的方法制备。式7.1的化合物,其中R3和R12如之前所描述,可以从式7.0的化合物来制备,通过以催化剂SbCl5在卤化溶剂如DCM中于约23℃的温度进行处理,如a中所指示。式7.2的化合物,其中R3和R12如之前所描述,可以从式7.1的化合物(其中R3和R12如之前所描述)制备,通过以氢化物试剂如硼烷二甲基硫化物复合物在催化剂如(R)-(+)-2-甲基-CBS-噁唑硼烷的存在下在极性质子溶剂如甲醇(MeOH)中于约23℃的温度进行处理,如b中所指明的。
方案7
式8.1的化合物,其中n为0或1且W为CH2或O,可以根据方案8,步骤a中概述的方法制备。式8.1的化合物,其中n为0或1,且W为CH2或O,可以从式8.0的化合物(其中n为0或1且W为CH2或O)制备,通过以碱如正丁基锂(n-BuLi)和醛如乙醛在极性非质子溶剂如THF中于约-78℃至23℃的温度进行处理,如a中所指示的。
方案8
式9.1的化合物,其中R3和R12如最初所定义,可以根据方案9,步骤a中概述的方法制备。式9.1的化合物,其中R3和R12如最初所定义,可以从式9.0的化合物(其中R3如最初所定义(式9.0可以购买获得,或者可以从不对称Shi环氧化对应的E-烯烃前体制备,如Wang,Z.-X.;Tu,Y.;Frohn,M;Zhang,J.-R.;Shi,Y.J.Am.Chem.Soc.1997,119,11224中所报道的)制备,通过以铜(I)盐如碘化亚酮(Cul)和有机金属亲核试剂如4-(三氟甲基)苯基溴化镁的预混合悬浮液在极性非质子溶剂如THF中于约-78℃至23℃的温度进行处理,如a中所示。
方案9
式10.2的化合物,其中R1、R2、R3、R4和R12如最初所定义,可以根据方案10,步骤a中概述的方法制备。式10.0的化合物,其中R1如最初所定义,可以以式10.1的醇(其中R2、R3、R4和R12如最初所定义)和偶联剂如3-(乙基亚氨基亚甲基氨基)-N,N-二甲基丙-l-胺盐酸盐(EDC)和催化剂如N,N-二甲基吡啶-4-胺(DMAP)在卤化溶剂如DCM中进行处理,得到式10.2的化合物,其中R1、R2、R3、R4和R12如之前所定义,如a中所显示。
方案10
式11.2的化合物,其中R1,R2,R3,R4,R6,R12和Z如最初所定义,可以根据方案11,步骤a–b中概述的方法制备。如a所描绘的,式11.2的化合物,其中R1,R2,R3,R4和R12如最初所定义,可以在卤化溶剂如DCM中遭遇酸如氯化氢(HCl)在二噁烷中的4当量浓度(N)溶液,得到式9.0的化合物,其中R1,R2,R3,R4和R12如最初所定义,如在a中显示的。
式11.0的化合物,其中R1,R2,R3,R4和R12如最初所定义,可以以式11.1的化合物(其中R6和Z如最初所定义)在碱如二异丙基乙胺(DIPEA)和肽偶联试剂如苯并三唑-l-基-氧基三吡咯烷基鏻六氟磷酸盐(PyBOP)的存在下在卤化溶剂如DCM中进行处理,得到式11.2的化合物,其中R1,R2,R3,R4,R5,R12和Z如最初所定义,如b中所显示。
方案11
式12.0的化合物,其中R1、R2、R3、R4、R6、R7、R12和Z如最初所定义,可以根据方案12,步骤a中概述的方法制备。如a中所示,式11.2的化合物,其中R1、R2、R3、R4、R6、R12和Z如最初所定义,可以使用或不使用试剂如碘化钠(Nal)和碱金属碳酸盐碱如碳酸钠(Na2CO3)或碳酸钾(K2CO3)在溶剂如丙酮中于约55℃的温度以适当的脂族饱和烃基卤化物进行处理,或者通过在胺碱如吡啶、三乙胺(Et3N)、DMAP或其混合物在非质子溶剂如DCM中于约23℃的温度以酰卤进行处理,得到式12.0的化合物,其中R1、R2、R3、R4、R6、R7、R12和Z如最初所定义。
方案12
实施例
下列实施例中的化学可以使用2-((叔丁氧基羰基)氨基)丙酸(Boc-Ala-OH)的对映异构体或受保护(PMB或Bn)或未经保护的乳酸乙酯的对映异构体进行。
实施例1:制备(S)-2-(苄基氧基)-l,l-双(4-氟苯基)丙-l-醇.
经10分钟(min)期间向(S)-2-(苄基氧基)丙酸乙酯(2.08克(g),10.0毫摩尔(mmol))在四氢呋喃(THF;20毫升(mL))中的溶液于0℃缓慢地添加(4-氟苯基)溴化镁(31.3mL,25.0mmol,0.8摩尔(M)在THF中)。反应容器经2小时(h)缓慢地温热至室温,并且反应混合物通过小心添加饱和(sat.)氯化铵水溶液(aq.)(NH4Cl;50mL)而淬灭。混合物以乙醚(Et2O;50mL)稀释,分离各相,并且水相以Et2O(2x50mL)萃取。合并的有机相以饱和氯化钠溶液(NaCl,盐水;100mL)洗涤,经硫酸钠(Na2SO4)干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(硅胶(SiO2),0→5%丙酮在己烷中),得到标题化合物(3.28g,93%),为无色油状物:1H NMR(300MHz,CDCl3)δ7.47–7.38(m,2H),7.38–7.27(m,5H),7.17–7.09(m,2H),7.04–6.89(m,4H),4.64(dd,J=11.4,0.7Hz,1H),4.51–4.38(m,2H),3.12(s,1H),1.11(d,J=6.1Hz,3H);19F NMR(376MHz,CDCl3)δ-116.19,-116.41;ESIMS m/z 377([M+Na]+).
实施例2A:制备(S)-4,4'-(2-(苄基氧基)丙烷-1,1-二基)双(氟苯).
向(S)-2-(苄基氧基)-1,1-双(4-氟苯基)丙-1-醇(709毫克(mg),2.00mmol)在二氯甲烷(DCM;20mL)中的溶液于0℃添加三乙基硅烷(Et3SiH;3.19mL,20.0mmol),接着添加2,2,2-三氟乙酸(TFA;1.53mL,20.0mmol)。混合物于0℃搅拌1h。所得溶液通过小心添加碳酸氢钠饱和水溶液(NaHCO3;20mL)淬灭。分离各相,并且水相以DCM(2x30mL)萃取。合并的有机相以盐水洗涤(50mL),经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(SiO2,0→10%丙酮在己烷中),得到标题化合物(627mg,92%),为白色固体:1H NMR(400MHz,CDCl3)δ7.31–7.22(m,5H),7.21–7.16(m,2H),7.10–7.03(m,2H),7.00–6.91(m,4H),4.54(dd,J=11.5,0.7Hz,1H),4.31(dd,J=11.6,0.8Hz,1H),4.14(dq,J=8.1,6.1Hz,1H),3.93(d,J=8.1Hz,1H),1.18(d,J=6.0Hz,3H);19F NMR(376MHz,CDCl3)δ-116.60,-117.10;ESIMS(m/z)361([M+Na]+).
实施例2B:制备(S)-(2-(苄基氧基)-1-甲氧基丙烷-1,1-二基)二苯
向氢化钠(NaH;52.0mg,1.30mmol,60%重量/重量(w/w)在矿物油中)在N,N-二甲基甲酰胺(DMF;3mL)中的悬浮液于0℃添加(S)-2-(苄基氧基)-l,l-二苯基丙-l-醇(318mg,1mmol)在DMF(1mL)中的溶液。反应混合物于室温搅拌30min并且然后冷却至0℃。添加碘甲烷(MeI;93.0微升(μl),1.50mmol),并且反应混合物于室温搅拌1h。所得溶液通过小心添加NaHCO3饱和水溶液(10mL)而淬灭。混合物以乙醚(Et2O;10mL)稀释,分离各相,并且水相以Et2O(2x10mL)萃取。合并的有机相以盐水洗涤(20mL),经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(SiO2,0→5%丙酮在己烷中),得到标题化合物(295mg,89%),为无色油状物:1H NMR(400MHz,CDCl3)δ7.47–7.41(m,2H),7.40–7.35(m,2H),7.33–7.18(m,11H),4.69(d,J=11.9Hz,1H),4.54(d,J=12.3Hz,1H),4.50(q,J=6.1Hz,1H),3.13(s,3H),1.10(d,J=6.1Hz,3H);13C NMR(101MHz,CDCl3)δ142.96,141.31,138.79,129.13,128.54,128.14,127.61,127.16,127.08,126.95,126.69,99.99,85.35,78.13,70.80,52.46,13.65;ESIMS(m/z)333([M+H]+).
实施例2C:制备(S)-(2-(苄基氧基)-1-氟丙-1,1-二基)二苯.
向(S)-2-(苄基氧基)-1,1-二苯基丙-l-醇(300mg,0.942mmol)在DCM(5mL)中的溶液于0℃添加(二乙基氨基)三氟化硫(DAST;1.88mL,1.88mmol,1M在DCM中)。反应经3h缓慢地温热至室温。所得溶液通过小心滴加NaHCO3饱和水溶液(5mL)而淬灭。分离各相,并且水相以DCM(2x10mL)萃取。合并的有机相以盐水洗涤(10mL),经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(SiO2,0→10%丙酮在己烷中),得到标题化合物(300mg,98%),为无色油状物:1H NMR(400MHz,CDCl3)δ7.58–7.49(m,2H),7.43–7.37(m,2H),7.36–7.20(m,9H),7.09–6.99(m,2H),4.47(d,J=11.7Hz,1H),4.37–4.25(m,2H),1.26(dd,J=6.3,1.3Hz,3H);13C NMR(101MHz,CDCl3)δ142.23(d,J=22.7Hz),141.00(d,J=23.5Hz),138.03,128.21,128.16,127.90(d,J=1.5Hz),127.80,127.72(d,J=1.7Hz),127.52,127.42(d,J=1.3Hz),126.23(d,J=9.6Hz),125.93(d,J=8.7Hz),99.96(d,J=180.8Hz),78.91(d,J=26.9Hz),71.68,14.47(d,J=3.6Hz);19F NMR(376MHz,CDCl3)δ-159.80.
实施例2D,步骤1:制备二硫代羧酸(S)-O-(2-(苄基氧基)-1,1-双(3,4,5-三氟苯基)丙基)S-甲基酯.
向(S)-2-(苄基氧基)-1,1-双(3,4,5-三氟苯基)丙-l-醇(496mg,1.16mmol)在无水THF(5.8mL)中的溶液添加NaH(93.0mg,2.33mmol),接着添加咪唑(3.96mg,0.0580mmol),并且反应混合物于环境温度搅拌1h。经由注射器一次性添加二硫化碳(562μl,9.30mmol),接着添加MeI(579μl,9.30mmol)并且反应混合物于环境温度搅拌2h。反应混合物以Et2O(5mL)稀释并以饱和NH4Cl水溶液(10mL)淬灭。分离各层,水层以Et2O(3x10mL)萃取。合并的有机层经硫酸镁(MgSO4)干燥,过滤并浓缩得到橙/棕色油状物。粗的油状物通过快速柱色谱纯化(SiO2,0→50%乙酸乙酯(EtOAc)在己烷中),得到标题化合物(627mg,94%),为澄清亮黄油状物:1H NMR(400MHz,CDCl3)δ7.40–7.27(m,3H),7.24–7.16(m,2H),7.02(dd,J=9.1,6.6Hz,2H),6.96(dd,J=8.8,6.5Hz,2H),5.44(q,J=6.1Hz,1H),4.66(d,J=11.6Hz,1H),4.51(d,J=11.6Hz,1H),2.49(s,3H),1.16(d,J=6.1Hz,3H);19F NMR(376MHz,CDCl3)δ-133.89(d,J=20.7Hz),-134.73(d,J=20.6Hz),-159.83(t,J=20.6Hz),-160.56(t,J=20.7Hz);(薄膜)2922,1721,1622,1595,1526,1436,1344,1241,1217,1197,1119,1088,1040,965,908,861,822,730,712,697,672cm-1.
实施例2D,步骤2:制备(S)-5,5'-(2-(苄基氧基)丙-1,1-二基)双(l,2,3-三氟苯)
二硫代羧酸(S)-O-(2-(苄基氧基)-1,1-双(3,4,5-三氟苯基)丙基)S-甲基酯(598mg,1.16mmol)在甲苯(200mL)中的溶液通过冻融泵方法在N2气氛下脱气(3个循环,使用液氮(N2))。然后添加三丁基氢化锡(3.12mL,11.6mmol),反应烧瓶配有回流冷凝管,并且反应混合物加热至轻微回流(115℃)。历经3h经由回流冷凝管下游的注射器添加偶氮二异丁腈(AIBN;0.200g,1.22mmol)在脱气甲苯(3个循环,经由液体N2;32mL)中的溶液。一旦缓慢添加AIBN完成,在回流条件下搅拌反应混合物过夜。真空除去溶剂,提供淡黄色油状物。粗油状物通过快速柱色谱纯化(SiO2,0→30%EtOAc在己烷中),得到标题化合物(358mg,72%),为澄清无色油状物:1H NMR(400MHz,CDCl3)δ7.28(d,J=6.6Hz,3H),7.17–7.06(m,2H),6.92(dd,J=8.5,6.5Hz,2H),6.79(dd,J=8.3,6.4Hz,2H),4.59(d,J=11.7Hz,1H),4.31(d,J=11.7Hz,1H),4.02(p,J=6.2Hz,1H),3.76(d,J=6.8Hz,1H),1.19(d,J=6.1Hz,3H);19F NMR(376MHz,CDCl3)δ-133.80(d,J=20.5Hz),-134.34(d,J=20.5Hz),-162.54(t,J=20.5Hz),-162.84(t,J=20.5Hz);(薄膜)2871,1621,1526,1445,1345,1262,1235,1116,1096,1043,859,802,728,698,679cm-1.
实施例3A:制备(S)-l,l-双(4-氟苯基)丙-2-醇
向(S)-4,4'-(2-(苄基氧基)丙-1,1-二基)双(氟苯)(575mg,1.70mmol)在乙醇(EtOH;11mL)和环己烯(5.5mL)中的溶液于室温添加钯/碳(Pd/C;362mg,0.0850mmol,2.5%w/w的Pd)。反应混合物于65℃搅拌2h,冷却至室温,经塞过滤,并浓缩,得到标题化合物(415mg,98%),为无色油状物:1H NMR(400MHz,CDCl3)δ7.36–7.29(m,2H),7.25–7.18(m,2H),7.09–6.93(m,4H),4.47(dqd,J=8.2,6.1,3.3Hz,1H),3.80(d,J=8.3Hz,1H),1.55(d,J=3.3Hz,1H),1.19(d,J=6.1Hz,3H);13C NMR(101MHz,CDCl3)δ162.90(d,J=23.3Hz),160.46(d,J=23.1Hz),138.15(d,J=3.1Hz),136.94(d,J=3.6Hz),130.14(d,J=7.8Hz),129.55(d,J=7.8Hz),115.70(d,J=18.8Hz),115.49(d,J=18.8Hz),70.07,58.61,21.63;19F NMR(376MHz,CDCl3)δ-115.84,-116.19.
实施例3B:制备(S)-1,1-双(2-氟苯基)丙-1,2-二醇
向(S)-1,1-双(2-氟苯基)-2-((4-甲氧基苄基)氧基)丙-1-醇(790mg,2.06mmol)在DCM(20mL)中的溶液于0℃添加Et3SiH(3.28mL,20.6mmol),接着添加TFA(1.57mL,20.6mmol)。混合物于0℃搅拌1h。所得溶液通过小心添加NaHCO3饱和水溶液(20mL)而淬灭。分离各相,并且水相以DCM(2x30mL)萃取。合并的有机相以盐水洗涤(50mL),经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(SiO2,0→10%丙酮在己烷中),得到标题化合物(388mg,71%),为无色油状物:1H NMR(400MHz,CDCl3)δ7.90–7.77(m,1H),7.70(tt,J=8.2,1.5Hz,1H),7.31–7.10(m,4H),6.97(ddd,J=12.7,8.1,1.3Hz,1H),6.88(ddd,J=11.8,8.0,1.4Hz,1H),5.11(qd,J=6.3,2.3Hz,1H),3.49(s,1H),2.27(s,1H),1.09(d,J=6.3Hz,3H);19F NMR(376MHz,CDCl3)δ-112.90(d,J=8.3Hz),-113.92(d,J=8.4Hz);ESIMS(m/z)551([2M+Na]+).
实施例3C:制备(S)-1,1-双(4-溴苯基)丙-2-醇
向(S)-1,1-双(4-溴苯基)-2-((4-甲氧基苄基)氧基)丙-1-醇(1.80g,3.56mmol)在DCM(18mL)中的溶液于0℃添加Et3SiH(5.68mL,35.6mmol),接着添加TFA(2.72mL,35.6mmol)。混合物经3h缓慢地温热至室温。所得溶液通过小心添加饱和NaHCO3水溶液(20mL)而淬灭。分离各相,水相以DCM(2x30mL)萃取。合并的有机相以盐水(50mL)洗涤,经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(SiO2,0→10%丙酮在己烷中),得到标题化合物(742mg,56%),为无色油状物:1H NMR(300MHz,CDCl3)δ7.51–7.36(m,4H),7.25–7.17(m,2H),7.18–7.06(m,2H),4.48(dq,J=8.2,6.1Hz,1H),3.76(d,J=8.2Hz,1H),2.80(s,1H),1.19(d,J=6.2Hz,3H);13C NMR(75MHz,CDCl3)δ140.94,139.85,131.98,131.85,130.39,129.84,121.06,120.72,69.82,58.91,21.65;(薄膜)3390,3024,2969,2900,1486,1072cm-1.
实施例3D,步骤1:制备(S)-1,1-双(4-((三甲基甲硅烷基)乙炔基)-苯基)丙-2-醇。
向(S)-1,1-双(4-溴苯基)丙-2-醇(1.01g,2.72mmol)在THF(9mL)中的溶液添加双(三苯基膦)二氯化钯(0.095g,0.136mmol)和碘化亚铜(I)(CuI;0.026g,0.136mmol)。混合物以N2冲洗20min,滴加三乙胺(Et3N;4.53mL)。向所得混合物中滴加乙炔基三甲基硅烷(1.15mL,8.15mmol),并且将混合物加热至回流并搅拌过夜。混合物冷却至室温,并且反应以饱和NaHCO3水溶液淬灭。产物以EtOAc(2x)萃取,并且合并的有机层以盐水洗涤,经Na2SO4干燥,过滤并浓缩。粗的剩余物然后通过快速柱色谱纯化(SiO2,0→20%丙酮在己烷中),提供标题化合物(495mg,45%),为棕色泡沫状物:1H NMR(400MHz,CDCl3)δ7.48–7.42(m,2H),7.42–7.37(m,2H),7.33–7.27(m,2H),7.24–7.17(m,2H),4.51(dqd,J=12.2,6.1,3.5Hz,1H),3.81(d,J=8.3Hz,1H),1.60(d,J=3.8Hz,1H),1.18(d,J=6.1Hz,3H),0.26(s,9H),0.26(s,9H);13C NMR(101MHz,CDCl3)δ142.55,141.48,132.42,132.29,128.69,128.15,121.90,121.57,104.76,104.71,94.49,94.33,69.76,59.96,21.55,0.00;(薄膜)3397,2960,2156,1501,1248,861,840cm-1;HRMS-ESI(m/z)[M+H]+C25H33OSi2,计算值,405.2064;测量值,405.2070.
实施例3D,步骤2:制备(S)-1,1-双(4-乙炔基苯基)丙-2-醇
向(S)-1,1-双(4-((三甲基甲硅烷基)乙炔基)苯基)丙-2-醇(0.470g,1.16mmol)在甲醇(MeOH;5.8mL)中的溶液添加碳酸钾(K2CO3;0.482g,3.48mmol)。混合物于室温搅拌1h并且然后经过滤。滤饼以MeOH洗涤,并且滤液经浓缩。粗物质通过快速柱色谱纯化(SiO2,0→20%丙酮在己烷中),提供标题化合物(288mg,95%),为黄色油状物:1H NMR(300MHz,CDCl3)δ7.48–7.43(m,2H),7.43–7.39(m,2H),7.35–7.29(m,2H),7.24–7.19(m,2H),4.51(dqd,J=8.3,6.1,3.7Hz,1H),3.82(d,J=8.3Hz,1H),3.05(s,1H),3.04(s,1H),1.63–1.55(m,1H),1.18(d,J=6.1Hz,3H);13C NMR(101MHz,CDCl3)δ142.84,141.82,132.60,132.48,128.74,128.22,120.87,120.57,83.31,83.29,77.39,77.29,69.73,59.96,21.66;(薄膜)3436,3280,2968,2106,1499,1075,825cm-1;HRMS-ESI(m/z)[M+H]+C19H17O,计算值,261.1274;测量值,261.1272.
实施例3D,步骤3:制备(S)-1,1-双(4-乙基苯基)丙-2-醇
向(S)-1,1-双(4-乙炔基苯基)丙-2-醇(0.144g,0.553mmol)在EtOAc(2.8mL)中的溶液添加钯(5%重量(wt)在碳上,干基;0.235g,0.055mmol)。混合物在氢气球下搅拌过夜。混合物经过滤,并且滤饼以EtOAc洗涤。合并的滤液然后经浓缩,并且粗剩余物通过快速柱色谱纯化(SiO2,0→25%丙酮在己烷中),得到标题化合物(97.0mg,65%),为澄清油状物:1H NMR(400MHz,CDCl3)δ7.33–7.25(m,2H),7.22–7.15(m,2H),7.18–7.11(m,2H),7.10(d,J=8.1Hz,2H),4.51(dqd,J=8.7,6.1,2.5Hz,1H),3.74(d,J=8.9Hz,1H),2.65–2.53(m,4H),1.68(d,J=2.8Hz,1H),1.23–1.14(m,9H);13C NMR(101MHz,CDCl3)δ142.74,142.33,139.94,138.91,128.48,128.40,128.07,128.02,70.19,60.02,28.41,28.39,21.37,15.47,15.46;(薄膜)3421,2963,1510,1110,821cm-1;HRMS-ESI(m/z)([M+Na]+)C19H24NaO,计算值,291.1719;测量值,291.1725.
实施例3E:制备1-(9H-呫吨-9-基)乙醇
向9H-呫吨(364mg,2.00mmol)在THF(10mL)中的溶液于-78℃添加正丁基锂(2.5M在己烷中;0.880mL,2.20mmol)。混合物于-78℃搅拌30min。添加乙醛(0.226mL,4.00mmol),并且反应混合物缓慢地温热至室温过夜。所得溶液通过小心添加饱和NH4C1水溶液(10mL)而淬灭。分离各相,并且水相以Et2O(2x15mL)萃取。合并的有机相以盐水洗涤(20mL),经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(SiO2,0→10%丙酮在己烷中),得到标题化合物(216mg,48%),为无色油状物:1H NMR(400MHz,CDCl3)δ7.33–7.22(m,4H),7.17–7.04(m,4H),3.99(d,J=5.1Hz,1H),3.96–3.82(m,1H),1.54(d,J=6.0Hz,1H),1.00(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ152.94,152.65,129.54,129.30,128.19,128.17,123.18,123.14,122.48,121.73,116.59,116.41,73.07,47.06,18.81;ESIMS(m/z)475([2M+Na]+).
实施例3F:制备(1S,2S)-l-苯基-l-(4-(三氟甲基)苯基)丙-2-醇
于室温向镁屑(102mg,4.20mmol)在Et2O(4mL)中的混合物添加l-溴-4-(三氟甲基)苯(0.588mL,4.20mmol),接着添加MeI(5μl)。使用加热枪加热至温和沸腾后,混合物变成黄/棕色。反应然后在水浴中于室温搅拌30min直到几乎消耗掉所有的镁。于-78℃将其添加到碘化亚铜(I)(CuI;400mg,2.10mmol)在Et2O(4mL)中的悬浮液中。反应于-20℃搅拌30min,然后冷却至-78℃,并且添加(2S,3S)-2-甲基-3-苯基环氧乙烷(0.201mL,1.50mmol)。所得混合物缓慢地温热至室温过夜。所得溶液通过小心添加饱和NH4Cl水溶液(10mL)淬灭。分离各相,并且水相以Et2O(2x15mL)萃取。合并的有机相以盐水洗涤(20mL),经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(Si02,0→10%丙酮在己烷中),得到标题化合物(390mg,94%),为浅黄色油状物:1H NMR(400MHz,CDCl3)δ7.60–7.50(m,2H),7.48–7.38(m,2H),7.38–7.33(m,4H),7.30–7.23(m,1H),4.58(dqd,J=8.4,6.1,3.5Hz,1H),3.88(d,J=8.5Hz,1H),1.65(d,J=3.6Hz,1H),1.20(d,J=6.1Hz,3H);19F NMR(376MHz,CDCl3)δ-62.49;ESIMS(m/z)263([M-OH]+).
实施例3G,步骤1:制备4,4'-(2-氧代丙-1,1-二基)二苯基氰
向4-溴苯基氰(546mg,3.00mmol)和碳酸铯(977mg,3.00mmol)在THF(10mL)中的悬浮液于N2气氛下添加丙酮(1.10mL,15.00mmol),接着添加X-Phos Pd G3(50.8mg,0.060mmol)。然后将小瓶密封并加热至55℃保持4天。反应以EtOAc(30mL)稀释并以饱和NH4Cl(3x10mL)、水(15mL)和盐水(15mL)洗涤。然后有机相经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(SiO2,0→40%EtOAc在己烷中),得到标题化合物(174mg,22%),为无色油状物:1H NMR(400MHz,CDCl3)δ7.66(d,J=8.4Hz,4H),7.34(d,J=8.3Hz,4H),5.21(s,1H),2.29(s,3H);13C NMR(101MHz,CDCl3)δ203.68,142.15,132.75,129.64,118.21,112.00,64.25,30.43;ESIMS m/z 261([M+H]+).
实施例3G,步骤2:制备(S)-4,4'-(2-羟基丙-1,1-二基)二苯基氰.
向4,4'-(2-氧代丙-l,1-二基)二苯基氰(174mg,0.668mmol)在甲苯(4.5mL)中的溶液添加(R)-l-甲基-3,3-二苯基六氢吡咯并[l,2-c][l,3,2]噁唑硼烷(1M在甲苯中的溶液,66.8μL,0.067mmol)。然后,反应冷却至0℃并且经2min添加BH3-DMS(69.8μl,0.735mmol)在0.5mL甲苯中的溶液。烧瓶于0℃搅拌。2h后,反应以甲醇(0.5mL)淬灭,以EtOAc稀释并添加水。分离各相,且水相以EtOAc x 2萃取。合并的有机相以盐水洗涤(20mL),经Na2SO4干燥,过滤并浓缩。所得油状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(99.7mg,57%),为无色油状物:1H NMR(400MHz,CDCl3)δd 7.60(dd,J=8.4,6.8Hz,4H),7.51–7.46(m,2H),7.43–7.37(m,2H),4.63–4.47(m,1H),3.97(d,J=7.5Hz,1H),1.97(d,J=3.8Hz,1H),1.21(d,J=6.2Hz,3H).13C NMR(101MHz,CDCl3)δ146.91,145.86,132.60,132.45,129.90,129.19,118.58,118.51,110.96,110.92,69.19,59.56,22.27;ESIMS m/z 263([M+H]+).
实施例3H,步骤1:制备3,3-二苯基丁-2-酮.
在空气气氛下向2,3-二苯基丁-2,3-二醇(500mg,2.06mmol)在DCM(10mL)中的机械搅拌的混合物添加五氯化锑(26.5μl,0.206mmol)。反应混合物于25℃搅拌1h并且然后通过缓慢滴加饱和NaHCO3水溶液淬灭。所得混合物以水和额外的DCM稀释,并且有机层通过流经分相器而分离。所得油状物通过快速柱色谱纯化(Si02,0-5%丙酮在己烷中),得到标题化合物(330mg,71%),为无色油状物:1H NMR(400MHz,CDCl3)δ7.36–7.31(m,4H),7.30–7.25(m,2H),7.23–7.15(m,4H),2.11(s,3H),1.87(s,3H);13C NMR(101MHz,CDCl3)δ209.16,143.59,128.36,126.91,62.32,27.62,26.42;ESIMS m/z 225([M+H]+).
实施例3H,步骤2:制备(S)-3,3-二苯基丁-2-醇.
向3,3-二苯基丁-2-酮(150mg,0.669mmol)在甲苯(4.5mL)中的溶液添加(R)-l-甲基-3,3-二苯基六羟基吡咯并[l,2-c][l,3,2]噁唑硼烷(1M在甲苯中的溶液,134μl,0.134mmol)。然后经2min将BH3-DMS(70.2μl,0.702mmol)在0.5mL的甲苯中的溶液添加到反应混合物中。烧瓶于室温搅拌。1h后,反应以甲醇(0.5mL)淬灭。添加DCM和水,且分离各相。水相以DCM(2x)萃取。合并的有机相以盐水洗涤(20mL),经Na2SO4干燥,过滤并浓缩。所得油状物通过快速柱色谱纯化(Si02,0→20%丙酮在己烷中),得到标题化合物(150mg,99%),为无色油状物:1H NMR(400MHz,CDCl3)δd 7.39-7.17(m,10H),4.70–4.61(m,1H),1.67(s,3H),1.51(d,J=4.9Hz,1H),1.11(d,J=6.3Hz,3H);13C NMR(101MHz,CDCl3)δ147.30,145.86,128.40,128.15,128.05,127.79,126.20,126.01,72.28,51.77,23.26,18.39;ESIMS m/z 227([M+H]+).
实施例3I,步骤1:制备(S)-1,1-双(2,3-二甲氧基苯基)丙-1,2-二醇。
向异丙基镁氯化锂(1.3M在THF中,6.1mL,8.00mmol)的溶液添加THF(2mL)和l-溴-2,3-二甲氧基苯(1.74g,8.00mmol)。所得棕色溶液加热至温和回流(75℃外部温度),保持2.5h,然后在冰水浴中冷却至0℃。然后经由注射器滴加(S)-2-羟基丙酸甲酯(0.191ml,2mmol)。反应于0℃搅拌1h,然后从冰浴取出并且于室温搅拌过夜。反应在冰水浴冷却至0℃,以水(20mL)、盐水(20mL)和Et2O(40mL)稀释,并且以1N HC1(8mL)淬灭。分离各相,并且水相以Et2O(20mL)萃取。合并有机相,经MgSO4干燥,过滤并浓缩提供油状物。通过自动化硅胶柱色谱纯化(5-50%EtOAc在己烷中),提供标题化合物(568mg,82%),为黄色结晶固体:1H NMR(300MHz,CDCl3)δ7.43(td,J=8.0,1.5Hz,2H),7.11(td,J=8.1,4.9Hz,2H),6.83(dd,J=8.1,1.4Hz,2H),5.06–4.82(m,1H),4.74(d,J=1.2Hz,1H),3.81(s,3H),3.80(s,3H),3.20(s,3H),3.04(s,3H),2.86(d,J=9.5Hz,1H),0.97(d,J=6.4Hz,3H);13C NMR(126MHz,CDCl3)δ152.89,152.82,146.94,145.53,139.56,138.92,123.32,123.26,122.01,119.01,111.30,79.20,77.22,60.07,59.26,55.77,55.64,18.34;HRMS-ESI(m/z)([M+Na]+)C19H24O6Na,计算值,371.1465;测量值,371.1456.
实施例3I,步骤2:制备1,1-双(2,3-二甲氧基苯基)丙-2-酮.
向(S)-1,1-双(2,3-二甲氧基苯基)丙-1,2-二醇(560mg,1.61mmol)在无水CH2Cl2(8mL)中的溶液于0℃添加三乙基硅烷(4.82mmol)和三氟乙酸(TFA,124μl.,1.61mmol)。所得溶液于0℃搅拌2h,然后从冰浴移除并且搅拌2h。添加TFA(248μL,3.2mmol),并且反应然后于室温搅拌过夜。反应以水(25mL)稀释并以CH2Cl2(3x25mL)萃取。有机萃取物经Na2SO4干燥,过滤并浓缩提供油状物。通过自动化硅胶柱色谱纯化(5-25%丙酮在己烷中)提供标题化合物(396mg,75%),为白色固体:1H NMR(300MHz,CDCl3)δ6.99(t,J=8.0Hz,2H),6.87(dd,J=8.2,1.5Hz,2H),6.67–6.54(m,2H),5.86(s,1H),3.87(s,6H),3.75(s,6H),2.25(s,3H);13C NMR(126MHz,CDCl3)δ207.18,152.69,147.02,132.23,123.74,121.61,111.64,60.36,55.74,51.96,29.80;HRMS-ESI(m/z)([M+Na]+)C19H22O5Na,计算值,353.1359;测量值,353.1353.
实施例3I,步骤3:制备1,1-双(2,3-二甲氧基苯基)丙-2-醇.
向1,1-双(2,3-二甲氧基苯基)丙-2-酮(356mg,1.08mmol)在甲醇(3.5mL)中的溶液添加硼氢化钠(61mg,1.6mmol)。所得溶液于室温搅拌20h,然后以饱和NH4Cl(1mL)淬灭,以水(20mL)稀释并以CH2Cl2(3x20mL)萃取。合并有机萃取物,经Na2SO4干燥,过滤并浓缩得到标题化合物(360mg,100%),为油状物:1H NMR(300MHz,CDCl3)δ7.16–6.88(m,4H),6.79(ddd,J=9.6,7.8,1.9Hz,2H),4.81(d,J=8.3Hz,1H),4.53–4.32(m,1H),3.84(s,3H),3.84(s,3H),3.77(s,3H),3.76(s,3H),2.04(d,J=4.2Hz,1H),1.22(d,J=6.2Hz,3H);13C NMR(126MHz,CDCl3)δ152.98,152.83,147.71,147.04,136.17,135.33,123.94,123.62,120.96,120.84,110.76,110.48,70.32,60.26,60.20,55.66,55.63,45.11,21.80;IR(无底物膜)3451,2935,2833,1582,1473,1428,1266,1215,1167,1125,1088,1068,1004,964,908,835,809,787,748,728.
实施例4A:制备(S)-2-{{叔丁氧基羰基)氨基)-丙酸(S)-1,1-二苯基丙-2-基酯.
向(S)-1,1-二苯基丙-2-醇(317mg,1.493mmol)在DCM(15mL)中的溶液于0℃添加(S)-2-((叔丁氧基谈及)氨基)丙酸(Boc-Ala-OH;311mg,1.64mmol)和N,N-二甲基吡啶-4-胺(DMAP;18.2mg,0.149mmol),接着添加Nl-((乙基亚胺基)亚甲基)-N3,N3-二甲基丙烷-1,3-二胺盐酸盐(EDC;573mg,2.99mmol),且反应混合物于室温搅拌过夜并浓缩得到黄色油状物。粗物质通过快速柱色谱纯化(SiO2,1→10%丙酮在己烷中),得到标题化合物(433mg,75%),为无色油状物:1H NMR(400MHz,CDCl3)δ7.42-7.07(m,1OH),5.80(dq,J=10.1,6.1Hz,1H),4.97(d,J=8.0Hz,1H),4.19-4.06(m,1H),4.03(d,J=10.1Hz,1H),1.41(s,9H),1.23(d,J=6.1Hz,3H),0.76(d,J=7.2Hz,3H);13C MR(101MHz,CDC13)δ172.83,154.96,141.52,141.26,128.79,128.50,128.10,128.08,126.91,126.67,79.62,73.10,57.98,49.21,28.33,19.31,17.98;ESIMS w/384([M+H]+).
实施例5,步骤1:制备(S)-1-(((S)-1,1-二苯基丙-2-基)氧基)-1-氧代丙-2-氯化铵.
向(S)-2-((叔丁氧基羰基)氨基)丙酸(S)-1,1-二苯基丙-2-基酯(化合物2;433mg,1.13mmol)在DCM(6mL)中的溶液添加HCl在二噁烷(2.8mL,1 1.3mmol)中的4N溶液,并且混合物于室温搅拌3h。溶剂在N2流下蒸发得到标题化合物(360mg,100%),为白色固体:ESIMS(m/z)284([M+H]+)。
实施例5,步骤2:制备(S)-2-(3-羟基-4-甲氧基吡啶酰胺基)丙酸(S)-1,1-二苯基丙-2-基酯.
(S)-1-(((S)-1,1-二苯基丙-2-基)氧基)-1-氧代丙-2-氯化铵(化合物46;361mg,1.13mmol)和3-羟基-4-甲氧基吡啶甲酸(210mg,1.24mmol)在DCM(11mL)中的溶液添加苯并三唑-l-基-氧基三吡咯烷基鏻六氟磷酸盐(PyBOP;646mg,1.24mmol)和N-乙基-N-异丙基丙-2-胺(DIPEA;0.651mL,3.72mmol),和反应混合物于室温搅拌2h。蒸发溶剂且粗油状物通过快速柱色谱纯化(SiO2,1→50%丙酮在己烷中),得到标题化合物(340mg,70%),为白色泡沫状物:1H NMR(400MHz,CDCl3)δ12.10(s,1H),8.34(d,J=8.0Hz,1H),7.98(d,J=5.2Hz,1H),7.38–7.06(m,10H),6.86(d,J=5.3,1H),5.83(dq,J=10.1,6.1Hz,1H),4.52(dq,J=8.1,7.2Hz,1H),4.06(d,J=10.2Hz,1H),3.93(s,3H),1.26(d,J=6.1Hz,3H),0.97(d,J=7.2Hz,3H);13C NMR(101MHz,CDCl3)δ171.67,168.53,155.34,148.72,141.38,141.13,140.40,130.48,128.80,128.50,128.10,128.03,126.95,126.70,109.39,73.57,57.93,56.07,47.85,19.24,17.61;HRMS–ESI(m/z)([M+H]+)C25H27N2O5,计算值,435.1920;测量值,435.1925。
实施例6A:制备(S)-2-(3-乙酰氧基-4-甲氧基吡啶酰胺基)丙酸(S)-1,1-二苯基丙-2-基酯
于室温向(S)-2-(3-羟基-4-甲氧基吡啶酰胺基)-丙酸(S)-1,1-二苯基丙-2-基酯(化合物90;70.0mg,0.161mmol)、Et3N(44.9μL,0.332mmol)和DMAP(3.94mg,0.032mmol)在DCM(3.2mL)中的溶液添加乙酰氯(17.2μL,0.242mmol),并且反应混合物搅拌2h。溶剂经蒸发,并且所得粗油状物通过快速柱色谱纯化(SiO2,l→40%丙酮在己烷中),得到标题化合物(75.0mg,97%),为无色油状物:1H NMR(400MHz,CDCl3)δ8.41(d,J=7.8Hz,1H),8.30(d,J=5.4Hz,1H),7.38–7.10(m,10H),6.97(d,J=5.4Hz,1H),5.82(dq,J=10.0,6.2Hz,1H),4.52(dt,J=8.2,7.1Hz,1H),4.05(d,J=10.1Hz,1H),3.87(s,3H),2.37(s,3H),1.24(d,J=6.1Hz,3H),0.89(d,J=7.1Hz,3H);13C NMR(101MHz,CDCl3)δ172.23,168.89,162.28,159.42,146.66,141.55,141.44,141.25,137.45,128.77,128.50,128.13,128.11,126.89,126.67,109.73,73.32,57.90,56.27,47.85,20.75,19.25,17.92;HRMS–ESI(m/z)([M+H]+)C27H29N2O6,计算值,477.2025;测量值,477.2019.
实施例6B:制备(S)-2-(3-(乙酰氧基甲氧基)-4-甲氧基吡啶酰胺基)丙酸(S)-1,1-二苯基丙-2-基酯.
于室温向(S)-2-(3-羟基-4-甲氧基吡啶酰胺基)-丙酸(S)-1,1-二苯基丙-2-基酯(化合物90;100mg,0.230mmol)和K2CO3(63.6mg,0.460mmol)在丙酮(4.6mL)中的悬浮液添加乙酸溴甲酯(33.9μL,0.345mmol),并且将混合物加热至55℃保持3h并且然后冷却至室温。溶剂经蒸发并且所得粗物质通过快速柱色谱纯化(SiO2,l→40%丙酮在己烷中),得到标题化合物(94.0mg,80%产率),为无色油状物:1H NMR(400MHz,CDCl3)δ8.25(d,J=5.4Hz,1H),8.22(d,J=7.9Hz,1H),7.34–7.09(m,10H),6.92(d,J=5.4Hz,1H),5.83(dq,J=10.1,6.2Hz,1H),5.72(d,J=0.7Hz,2H),4.60–4.49(m,1H),4.06(d,J=10.1Hz,1H),3.88(s,3H),2.05(s,3H),1.25(d,J=6.1Hz,3H),0.91(d,J=7.2Hz,3H);13C NMR(101MHz,CDCl3)δ172.33,170.25,162.88,160.24,145.70,143.91,142.54,141.48,141.25,128.76,128.49,128.12,128.09,126.89,126.65,109.56,89.50,73.27,57.92,56.17,48.07,20.86,19.25,17.73;HRMS–ESI(m/z)[M+H]+C28H31N2O7,计算值,507.2131;测量值,507.2125.
实施例6C:制备(S)-2-(3-((异丁酰基氧基)甲氧基)-4-甲氧基吡啶酰胺基)丙酸(S)-1,1-二苯基丙-2-基酯.
向(S)-2-(3-羟基-4-甲氧基吡啶酰胺基)-丙酸(S)-1,1-二苯基丙-2-基酯(化合物90;100mg,0.230mmol)在丙酮(4.6mL)中的溶液添加碳酸钠(Na2CO3;73.2mg,0.690mmol)、碘化钠(NaI;6.90mg,0.046mmol)和2-乙氧基乙酸氯甲基酯(62.9mg,0.460mmol)。将混合物加热至55℃过夜且然后冷却至室温,且蒸发溶剂。所得剩余物通过快速柱色谱纯化(SiO2,2→30%丙酮在己烷中),得到标题化合物(79.0mg,64%),为无色油状物:1H NMR(400MHz,CDCl3)δ8.28(d,J=7.9Hz,1H),8.25(d,J=5.3Hz,1H),7.36–7.08(m,10H),6.92(d,J=5.4Hz,1H),5.83(dq,J=10.1,6.2Hz,1H),5.79–5.69(m,2H),4.62–4.44(m,1H),4.06(d,J=10.1Hz,1H),3.86(s,3H),2.53(hept,J=7.0Hz,1H),1.25(d,J=6.2Hz,3H),1.13(d,J=7.0Hz,6H),0.91(d,J=7.2Hz,3H);13C NMR(101MHz,CDCl3)δ176.22,172.34,162.85,160.23,145.55,144.16,142.18,141.48,141.26,128.76,128.49,128.12,128.09,126.89,126.65,109.48,89.90,73.26,57.93,56.12,48.07,33.85,19.26,18.68,17.74;HRMS–ESI(m/z)([M+H]+)C30H35N2O7,计算值,535.2444;测量值,535.2431。
实施例A:评价杀真菌活性:小麦叶斑枯病(Leaf Blotch of Wheat)(小麦叶斑病病原菌(Zymoseptoria tritici);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,直至径流(run-off)。对所有受喷洒的植物进行空气干燥然后进一步处理。除非另有说明,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。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%Trycol5941。
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,用小麦叶斑病病原菌(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(Wheat Glume Blotch)(小麦颖枯病菌(Leptosphaeria nodorum);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(Apple Scab)(苹果黑星病菌(Venturiainaequalis);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: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F: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,直至径流(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G: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,且当第一片叶完全形成时用于试验中。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20℃、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H: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I:评价杀真菌活性:番茄早疫病(Tomato Early Blight)(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,将植物保持在22℃、100%相对湿度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J: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小时用瓜类炭疽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.化合物结构制备方法和外观
*Cmpd.No.–化合物编号
表2.分析数据
*Cmpd.No.–化合物编号
表3.生物测试等级评定量表
表4.生物活性–以高体积施用和低体积施用的PUCCRT和SEPTTR疾病防治
*Cmpd.No.–化合物编号
*PUCCRT-小麦褐锈病(Wheat Brown Rust)(小麦叶锈菌(Puccinia triticina))
*SEPTTR-小麦斑枯病(Wheat Leaf Blotch)(小麦叶斑病病原菌(Zymoseptoriatritici))
*1DP–1天保护剂
*3DC–3天治疗剂
*g/H–克/公顷
*ppm–每百万分之一
表5:生物活性-在100ppm的病害防治
*Cmpd.No.–化合物编号
*ALTESO–番茄早疫病(Tomato Early Blight)(番茄早疫病菌(Alternariasolani))
*CERCBE–甜菜褐斑病(Leaf Spot of Sugar Beets)(甜菜尾孢菌(Cercosporabeticola))
*COLLLA–瓜类炭疽病(Cucumber Anthracnose)(黄瓜炭疽病(Colletotrichumlagenarium))
*LEPTNO–小麦颖枯病(Wheat Glume Blotch)(小麦颖枯病菌(Leptosphaerianodorum))
*1DP–1天保护剂
表6:生物活性-在100ppm的病害防治
*Cmpd.No.–化合物编号
*PYRIOR–.稻瘟病(Rice Blast)(稻瘟病菌(Pyricularia oryzae))
*RHYNSE–大麦烫伤(Barley Scald)(大麦云纹病菌(Rhynchosporium secalis))
*VENTIN–苹果黑星病(Apple Scab)(苹果黑星病菌(Venturia inaequalis))
*1DP–1天保护剂
表7.生物活性-在25ppm的病害防治
*Cmpd.No.–化合物编号
*PHAKPA–亚洲大豆锈病(Asian Soybean Rust)(豆薯层锈菌(Phakopsorapachyrhizi))
*1DP–1天保护剂
*3DC–3天治疗剂
Claims (10)
2.根据权利要求1所述的方法,其中所述催化剂为SbCl5。
3.根据权利要求1-2任一项所述的方法,其中所述溶剂为二氯甲烷。
4.根据权利要求1-3任一项所述的方法,其中所述反应条件a在23℃进行。
5.根据权利要求1-4任一项所述的方法,其中R3选自芳基,其任选取代有0、1或多个R8。
6.根据权利要求1-5任一项所述的方法,其中R12选自芳基,其任选取代有0、1或多个R8。
7.根据权利要求1-6任一项所述的方法,其中R3为芳基,R12为芳基,并且R3和R12均各自取代有1个R8。
8.根据权利要求1-7任一项所述的方法,其中每个R8为卤素。
9.根据权利要求1-7任一项所述的方法,其中每个R8为烷基。
10.根据权利要求1-8任一项所述的方法,其中每个R8为氟。
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