JP2018501271A - 殺真菌活性を有するピコリンアミド化合物 - Google Patents
殺真菌活性を有するピコリンアミド化合物 Download PDFInfo
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- JP2018501271A JP2018501271A JP2017534554A JP2017534554A JP2018501271A JP 2018501271 A JP2018501271 A JP 2018501271A JP 2017534554 A JP2017534554 A JP 2017534554A JP 2017534554 A JP2017534554 A JP 2017534554A JP 2018501271 A JP2018501271 A JP 2018501271A
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- compound
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- alkyl
- nmr
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- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title abstract description 4
- 230000000855 fungicidal effect Effects 0.000 title description 44
- 150000001875 compounds Chemical class 0.000 claims description 287
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 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 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 24
- -1 isobutenyl Chemical group 0.000 description 215
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 129
- 239000000203 mixture Substances 0.000 description 108
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
- 239000012071 phase Substances 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- 238000002360 preparation method Methods 0.000 description 63
- 239000011541 reaction mixture Substances 0.000 description 63
- 241000196324 Embryophyta Species 0.000 description 61
- 239000012230 colorless oil Substances 0.000 description 51
- 229910004298 SiO 2 Inorganic materials 0.000 description 48
- 239000011734 sodium Substances 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000003818 flash chromatography Methods 0.000 description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 238000000034 method Methods 0.000 description 38
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- 201000010099 disease Diseases 0.000 description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 33
- 239000003921 oil Substances 0.000 description 33
- 235000019198 oils Nutrition 0.000 description 33
- 239000012074 organic phase Substances 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000009472 formulation Methods 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000010409 thin film Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- 241000209140 Triticum Species 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 239000003880 polar aprotic solvent Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 235000021307 Triticum Nutrition 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 10
- 239000012038 nucleophile Substances 0.000 description 10
- 239000000575 pesticide Substances 0.000 description 10
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 238000011081 inoculation Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000013058 crude material Substances 0.000 description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 6
- 239000002480 mineral oil Substances 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
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- BWCRDMRLKBPUTD-VIFPVBQESA-N (2s)-2-phenylmethoxypropan-1-ol Chemical compound OC[C@H](C)OCC1=CC=CC=C1 BWCRDMRLKBPUTD-VIFPVBQESA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VZHJIJZEOCBKRA-UHFFFAOYSA-N 1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1 VZHJIJZEOCBKRA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 239000012448 Lithium borohydride Substances 0.000 description 4
- 239000002169 Metam Substances 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 241001246061 Puccinia triticina Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 230000000361 pesticidal effect Effects 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 230000003032 phytopathogenic effect Effects 0.000 description 4
- 230000000644 propagated effect Effects 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 4
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 4
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- GTNUYQXRNAXACS-NSHDSACASA-N (2R)-3-methyl-2-phenoxybutanal Chemical compound CC([C@H](C=O)OC1=CC=CC=C1)C GTNUYQXRNAXACS-NSHDSACASA-N 0.000 description 3
- SAIBLMXTNPSJPL-WMLDXEAASA-N (2R,3S)-2-phenoxy-3-phenylmethoxybutan-1-ol Chemical compound C(C1=CC=CC=C1)O[C@H]([C@@H](CO)OC1=CC=CC=C1)C SAIBLMXTNPSJPL-WMLDXEAASA-N 0.000 description 3
- 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 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 3
- OBHHCPRYWZKEIM-UHFFFAOYSA-N 3-hydroxy-4-methoxypyridine-2-carboxylic acid Chemical compound COC1=CC=NC(C(O)=O)=C1O OBHHCPRYWZKEIM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000213004 Alternaria solani Species 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 241000222235 Colletotrichum orbiculare Species 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 241001330975 Magnaporthe oryzae Species 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241000736122 Parastagonospora nodorum Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241001515790 Rhynchosporium secalis Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 241000228452 Venturia inaequalis Species 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 241001360088 Zymoseptoria tritici Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 229910000085 borane Inorganic materials 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 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 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 3
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 3
- 229960002523 mercuric chloride Drugs 0.000 description 3
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- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- 229950004921 temefos Drugs 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- TVDHEHMZOINJJW-UHFFFAOYSA-N tert-butyl cyclopent-2-en-1-yl carbonate Chemical compound CC(C)(C)OC(=O)OC1CCC=C1 TVDHEHMZOINJJW-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical group COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical group CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- ICTQUFQQEYSGGJ-UHFFFAOYSA-N thiocyclam oxalate Chemical compound OC(=O)C(O)=O.CN(C)C1CSSSC1 ICTQUFQQEYSGGJ-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical compound C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- URCWYLYUZXHYHZ-UHFFFAOYSA-N triphenylbismuth(2+) Chemical compound C1=CC=CC=C1[Bi+2](C=1C=CC=CC=1)C1=CC=CC=C1 URCWYLYUZXHYHZ-UHFFFAOYSA-N 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
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- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Biodiversity & Conservation Biology (AREA)
- Ecology (AREA)
- Forests & Forestry (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
本出願は、2014年12月30日出願の米国特許仮出願第62/098089号、2014年12月30日出願の同第62/098097号、2015年11月13日出願の同第62/255144号、2015年11月13日出願の同第62/255152号、2015年11月13日出願の同第62/255163号、2015年11月13日出願の同第62/255168号、2015年11月13日出願の同第62/255125号および2015年11月13日出願の同第62/255131号の利益を主張し、これらは参照として本明細書に明確に組み込まれる。
Yは、水素、C(O)R5またはQであり;
Qは、下記式:
R1およびR11は、水素またはアルキルから独立して選択され、0、1つまたは複数のR8で置換されており、あるいは、R1およびR11は、一緒になって、3員〜6員の飽和または部分的に飽和されている炭素環または複素環を形成してもよく、0、1つまたは複数のR8で置換されており;
R2およびR12は、水素、アルキル、アリールまたはアルケニルから独立して選択され、それぞれ0、1つまたは複数のR8で置換されており;
R3は、水素、C2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R4は、アルキル、アリールまたはアシルから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R5は、アルコキシまたはベンジルオキシから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R6は、水素、アルコキシまたはハロから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R7は、水素、−C(O)R9または−CH2OC(O)R9から選択され;
R8は、水素、アルキル、アリール、アシル、ハロ、アルケニル、アルコキシまたはヘテロシクリルから選択され、それぞれ0、1つまたは複数のR10で置換されており;
R9は、アルキル、アルコキシまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R10は、水素、アルキル、アリール、アシル、ハロ、アルケニル、アルコキシまたはヘテロシクリルから選択される]の化合物を含むことができる。
以下のスキームは、式(I)のピコリンアミド化合物を生成する手法を例示する。以下の記載および例は、例示の目的で提供され、置換基または置換パターンに関して限定するものとして解釈されるべきではない。
CH2Cl2(4mL)およびsat.aq.NaHCO3(1mL)中の(2R,3R)−4−メチル−3−フェノキシペンタン−1,2−ジオール(0.5g、2.38mmol)の溶液に、過ヨウ素酸ナトリウム(2.034g、9.51mmol)を加え、混合物を、TLCがジオールの完全な消費を示すまで激しく撹拌した。反応混合物を濾過し、濾液をH2Oで洗浄し、Na2SO4で乾燥し、濾過し、濃縮して、中間体アルデヒドの(R)−3−メチル−2−フェノキシブタナールを得て、それを更に精製することなく使用した。
MeOH(3.3mL)中の粗(R)−3−メチル−2−フェノキシブタナール(約1mmol)の溶液に、NaBH4(76mg、2.0mmol)を一度に加え、混合物を、TLCがアルデヒドの完全な消費を示すまで撹拌した。反応混合物を、sat.aq.NH4Cl(10mL)により注意深くクエンチし、CH2Cl2で希釈し、相を分離した。aq.相を、CH2Cl2(2×)で抽出し、合わせた有機相を、相分離器のカートリッジに通して乾燥した。溶媒を蒸発させ、得られた粗材料をフラッシュカラムクロマトグラフィー(SiO2、ヘキサン中0→15%のアセトン)により精製して、標記化合物(170mg、94%)を無色の油状物として得た。1H NMR (400 MHz, CDCl3) δ 7.32- 7.24 (m, 2H), 7.00- 6.91 (m, 3H), 4.15 (td, J = 6.1, 3.6 Hz, 1H), 3.88- 3.73 (m, 2H), 2.14- 2.01 (m, 1H), 1.80 (dd, J = 7.3, 5.6 Hz, 1H), 1.01 (d, J = 6.9 Hz, 3H), 0.97 (d, J = 6.9 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 158.86, 129.57, 121.18, 116.35, 83.94, 62.27, 29.25, 18.62, 18.09;ESIMS m/z 181(([M+H]+))。
THF中の臭化エチルマグネシウム(EtMgBr、3.99mL、4mmol、THF中1M)の溶液に、−78℃で、THF(6mL)中の粗(R)−3−メチル−2−フェノキシブタナール(約2mmol)の溶液を加え、混合物を、TLCがアルデヒドの完全な消費を示すまで撹拌した。反応混合物を、sat.aq.NH4Clにより注意深くクエンチし、Et2Oで希釈し、相を分離した。aq.相をEt2Oで抽出し、合わせた有機相をNa2SO4で乾燥し、濾過し、濃縮した。粗残渣を、フラッシュカラムクロマトグラフィー(SiO2、ヘキサン中0→10%のアセトン)により精製して、標記化合物(187mg、45%)を無色の油状物として得た。1H NMR (400 MHz, CDCl3) δ 7.29- 7.22 (m, 2H), 7.00- 6.96 (m, 2H), 6.95- 6.89 (m, 1H), 4.11 (t, J = 5.3 Hz, 1H), 3.80- 3.71 (m, 1H), 2.15- 2.03 (m, 1H), 1.76- 1.64 (m, 1H), 1.57 (d, J = 4.5 Hz, 1H), 1.49 (ddd, J = 14.3, 9.6, 7.2 Hz, 1H), 1.02 (d, J = 6.8 Hz, 3H), 1.01 (t, J = 7.5 Hz, 3H), 0.97 (d, J = 6.9 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 160.03, 129.50, 120.80, 116.01, 85.65, 73.83, 29.86, 25.33, 19.88, 18.19, 10.36;EIMS m/z 208。
CH2Cl2(3.4mL)中の(S)−(1R,2S)−1−シクロペンチル−1−(シクロプロピルメトキシ)プロパン−2−イル−2−((tert−ブトキシカルボニル)アミノ)プロパノエート(189mg、0.512mmol)の溶液に、ジオキサン中HClの4N溶液(2.6mL、10.2mmol)を加え、混合物を室温で3h撹拌した。溶媒をN2流下で蒸発させて、中間体アミン塩酸塩の(S)−1−(((1R,2S)−1−シクロペンチル−1−(シクロプロピルメトキシ)プロパン−2−イル)オキシ)−1−オキソプロパン−2−アミニウムクロリドを、白色の固体として得た。ESIMS m/z 340([M+H]+)。
CH2Cl2(3.4mL)中の(S)−1−(((1R,2S)−1−シクロペンチル−1−(シクロプロピルメトキシ)プロパン−2−イル)オキシ)−1−オキソプロパン−2−アミニウムクロリドおよび3−ヒドロキシ−4−メトキシピコリン酸(95.0mg、0.563mmol)の溶液に、N−エチル−N−イソプロピルプロパン−2−アミン(294μL、1.69mmol)およびPyBOP(293mg、0.563mmol)を加え、反応混合物を室温で4h撹拌した。溶媒を蒸発させ、粗油状物をフラッシュカラムクロマトグラフィー(SiO2、ヘキサン中1→50%のアセトン)により精製して、標記化合物(118mg、55%)を白色の固体として得た。1H NMR (300 MHz, CDCl3) δ 12.13 (d, J = 0.6 Hz, 1H), 8.47 (d, J = 7.9 Hz, 1H), 7.99 (d, J = 5.2 Hz, 1H), 6.88 (dd, J = 5.3, 0.6 Hz, 1H), 5.09 (qd, J = 6.5, 2.3 Hz, 1H), 4.78- 4.66 (m, 1H), 3.95 (s, 3H), 3.51 (dd, J = 9.8, 6.9 Hz, 1H), 3.23 (dd, J = 9.9, 6.8 Hz, 1H), 3.17 (dd, J = 8.5, 2.3 Hz, 1H), 2.01- 1.72 (m, 2H), 1.75- 1.45 (m, 6H), 1.56 (d, J = 7.2 Hz, 3H), 1.46- 1.29 (m, 1H), 1.28 (d, J = 6.6 Hz, 3H), 1.11- 0.96 (m, 1H), 0.55- 0.41 (m, 2H), 0.15- 0.06 (m, 2H); 13C NMR (101 MHz, CDCl3) δ 171.45, 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]+)C22H33N2O6の計算値421.2333、実測値421.2331。
CH2Cl2(1.6mL)中の(S)−(2S,3R)−3−(ベンジルオキシ)ヘキサ−5−エン−2−イル−2−((tert−ブトキシカルボニル)−アミノ)プロパノエート(182mg、0.483mmol)の溶液に、0℃で、2,2,2−トリフルオロ酢酸(TFA、400μL、5.19mmol)を30秒間かけて滴加し、得られた橙色の混合物を室温に温め、室温で2h撹拌した。反応混合物を、CH2Cl2(5mL)で希釈し、sat.aq.NaHCO3(5mL)で洗浄し、相を分離した。aq.相をCH2Cl2(3×5mL)で抽出し、合わせた有機相を、相分離器のカートリッジに通して乾燥し、濃縮して、中間体アミンの(S)−(2S,3R)−3−(ベンジルオキシ)ヘキサ−5−エン−2−イル−2−アミノプロパノエート(135mg、100%)を透明な無色の油状物として得て、それを次の工程に直接使用した。HRMS−ESI(m/z)([M+H]+)C16H24NO3の計算値278.1751、実測値278.1752。
CH2Cl2(4.87mL)中の(S)−(2S,3R)−3−(ベンジルオキシ)ヘキサ−5−エン−2−イル−2−アミノプロパノエート(135mg、0.487mmol)、3−ヒドロキシ−4−メトキシピコリン酸(99mg、0.584mmol)およびPYBOP(304mg、0.584mmol)の溶液に、N−エチル−N−イソプロピルプロパン−2−アミン(305μL、1.75mmol)を45秒間(sec)かけて滴加し、反応混合物を室温で一晩撹拌した。混合物を濃縮し、得られた橙色/褐色の油状物を、フラッシュカラムクロマトグラフィー(SiO2、ヘキサン中0→50%のアセトン)により精製して、標記化合物(212mg、86%)を透明な無色の油状物として得た。IR(薄膜)3369,3063,2981,2940,2877,1737,1648,1576,1528,1481,1452,1438cm−1;1H NMR (400 MHz, CDCl3) δ 12.12 (d, J = 0.6 Hz, 1H), 8.49 (d, J = 7.9 Hz, 1H), 7.94 (d, J = 5.2 Hz, 1H), 7.38- 7.19 (m, 5H), 6.83 (dd, J = 5.2, 2.6 Hz, 1H), 5.84 (ddt, J = 17.2, 10.2, 7.0 Hz, 1H), 5.20- 5.00 (m, 3H), 4.79- 4.66 (m, 1H), 4.62 (d, J = 11.5 Hz, 1H), 4.52 (d, J = 11.5 Hz, 1H), 3.92 (s, 3H), 3.57 (ddd, J = 7.2, 5.3, 3.5 Hz, 1H), 2.42- 2.24 (m, 2H), 1.54 (d, J = 7.2 Hz, 3H), 1.31 (d, J = 6.5 Hz, 3H);HRMS−ESI(m/z)([M+H]+)C23H29N2O6の計算値429.2020、実測値429.2025。
THF(6mL)中の(S)−(2S,3R,4R)−4−ベンジル−3−イソブトキシヘキサン−2−イル−2−((((9H−フルオレン−9−イル)メトキシ)−カルボニル)アミノ)プロパノエート(350mg、0.63mmol)の溶液に、モルホリン(0.63mL、7.2mmol)を加え、得られた溶液を室温で4日間撹拌した。混合物を濾過し、濾液を蒸発させて、粘性の白色の固体を得て、それを逆相カラムクロマトグラフィー(C18、H2O中CH3CN、NaOAc緩衝液)により精製して、中間体アミニウムアセテートの1−(((2S,3R,4R)−4−ベンジル−3−イソブトキシヘキサン−2−イル)オキシ)−1−オキソプロパン−2−アミニウムアセテートを得た。アミニウムアセテートをEtOAc(10mL)に溶解し、sat.aq.NaHCO3で洗浄し、相を分離した。有機相をNa2SO4で乾燥し、濾過し、濃縮して、中間体アミンの(2S,3R,4R)−4−ベンジル−3−イソブトキシヘキサン−2−イル−2−アミノプロパノエート(90mg、43%、アミン担持炭素でのジアステレオマーの1.5:1混合物)を、無色の油状物として得た。1H NMR (400 MHz, CDCl3)、2種のジアステレオマー δ 7.31- 7.22 (m, 2H), 7.21- 7.12 (m, 3H), 5.22- 5.09 (m, 1H), 3.52 (adq, J = 8.9, 7.0 Hz, 1H), 3.42 (atd, J = 8.5, 6.4 Hz, 1H), 3.30 (at, J = 4.9 Hz, 1H), 3.24 (addd, J = 8.4, 6.4, 4.3 Hz, 1H), 2.98 (adt, J = 13.8, 3.8 Hz, 1H), 2.43 (addd, J = 13.6, 9.9, 2.6 Hz, 1H), 1.92- 1.81 (m, 1H), 1.72 (adp, J = 15.7, 5.1 Hz, 1H), 1.58 (bs, 2H), 1.40- 1.24 (m, 2H), 1.34 (ad, J = 7.0 Hz, 3H), 1.31- 1.27 (m, 3H), 0.94 (ad, J = 6.7 Hz, 6H), 0.87 (atd, J = 7.5, 3.1 Hz, 3H).
CH2Cl2(1.5mL)中の(2S,3R,4R)−4−ベンジル−3−イソブトキシヘキサン−2−イル−2−アミノプロパノエート(0.09g、0.268mmol)、3−ヒドロキシ−4−メトキシピコリン酸(0.05g、0.295mmol)およびPYBOP(0.209g、0.402mmol)の懸濁液に、N−エチル−N−イソプロピルプロパン−2−アミン(0.141mL、0.805mmol)を加え、得られた暗褐色の溶液を室温で48h撹拌した。反応混合物を、EtOAcとaq.1N HClに分配し、相を分離した。有機相をsat.aq.NaHCO3で洗浄し、Na2SO4で乾燥し、濾過し、濃縮した。得られた粗残渣を、フラッシュカラムクロマトグラフィー(SiO2、ヘキサン中30%のEtOAc)により精製して、標記化合物の(アミン担持炭素での)ジアステレオマーの1.5:1混合物(125mg、96%)を無色の油状物として得た。1H NMR (400 MHz, CDCl3)、2種のジアステレオマー δ 12.15 (add, J = 11.4, 0.5 Hz, 1H), 8.49 (at, J = 8.0 Hz, 1H), 7.97 (add, J = 5.2, 3.5 Hz, 1H), 7.31- 7.19 (m, 2H), 7.15 (m, 3H), 6.86 (ad, J = 5.1 Hz, 1H), 5.25- 5.16 (m, 1H), 4.76- 4.66 (m, 1H), 3.94 (s, 3H), 3.42 (add, J = 8.5, 6.4 Hz, 1H), 3.33 (aq, J = 5.0 Hz, 1H), 3.22 (addd, J = 17.7, 8.5, 6.4 Hz, 1H), 2.97 (add, J = 13.8, 4.3 Hz, 1H), 2.42 (addd, J = 13.6, 10.0, 3.2 Hz, 1H), 1.89 - 1.77 (m, 1H), 1.73 (apptt, J = 10.2, 4.8 Hz, 1H), 1.56 (d, J = 7.2 Hz, 3H), 1.39- 1.25 (m, 2H), 1.37- 1.22 (m, 3H), 0.96- 0.81 (m, 9H); 13C NMR (101 MHz, CDCl3)、2種のジアステレオマー δ 171.51, 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]+))。
無水CH2Cl2(5mL)中の(R)−2,4−ジメチル−3−フェノキシペンタン−2−イル2−((tert−ブトキシカルボニル)アミノ)プロパノエート(197mg、0.519mmol)の溶液に、2,6−ルチジン(302μL、2.60mmol)、続いてトリフルオロメタンスルホン酸トリメチルシリル(281μL、1.56mmol)を加え、得られた溶液を室温で4h撹拌した。反応混合物をMeOH(2.5mL)で希釈し、得られた溶液を室温で30min撹拌し、濃縮して、中間体アミン塩の(R)−2,4−ジメチル−3−フェノキシペンタン−2−イル2−アミノプロパノエートトリフルオロメタンスルホネート(223mg、100%)を黄色の油状物として得た。ESIMS m/z 280.4(([M+H]+))。
無水CH2Cl2(5mL)中の(R)−2,4−ジメチル−3−フェノキシペンタン−2−イル2−アミノプロパノエートトリフルオロメタンスルホネート(223mg、0.519mmol)の溶液に、3−ヒドロキシ−4−メトキシピコリン酸(97mg、0.57mmol)、PyBOP(297mg、0.571mmol)およびHunig塩基(299μL、1.71mmol)を加え、得られた混合物を室温で2h撹拌し、濃縮し、残渣をカラムクロマトグラフィー(SiO2、ヘキサン中4→40%のアセトン)により精製して、標記化合物(24mg、11%)を油状物として得た。1H NMR (400 MHz, CDCl3) δ 12.18 (d, J = 3.7 Hz, 1H), 8.40 (d, J = 7.6 Hz, 1H), 7.99 (d, J = 5.0 Hz, 1H), 7.26- 7.17 (m, 2H), 6.96 (dd, J = 7.8, 4.9 Hz, 2H), 6.92- 6.80 (m, 2H), 4.67 (dd, J = 19.2, 4.4 Hz, 1H), 4.47 (dp, J = 29.2, 7.2 Hz, 1H), 3.94 (s, 3H), 2.12 (ddt, J = 13.8, 6.9, 3.3 Hz, 1H), 1.62- 1.54 (m, 6H), 1.38- 1.31 (m, 3H), 1.06 (dd, J = 6.9, 2.2 Hz, 3H), 1.01 (d, J = 6.8 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 171.32, 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]+)C23H31N2O6の計算値431.2177、実測値431.2187。
工業銘柄の材料をアセトンに溶解し、次にこれを、110ppmのトリトンX−100を含有する9容量の水と混合した。殺真菌剤溶液を、自動吹付散布機(automated booth sprayer)を使用してコムギ実生に流出するまで施用した。散布された植物を、全て、更なる取り扱いの前に風乾した。特記しない限りは、全ての殺真菌剤を、前述の方法を使用して全ての標的の病気に対するこれらの活性について評価した。コムギの葉枯病および褐色さび病の活性も、軌道散布施用(track spray application)を使用して評価し、この場合、0.1%のTrycol 5941を散布液剤に含有するEC製剤として、殺真菌剤を製剤化した。
コムギ植物(品種Yuma)を、温室において50%鉱質土壌/50%無土壌Metroミックス中の種から、第一葉が完全に出現するまで、1ポットあたり7〜10個の実生で成長させた。これらの植物には、殺真菌剤処理の前または後のいずれかにおいてプッシニアトリチシナ(Puccinia triticina)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の暗霧室に一晩保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が発症するように、24℃に設定した温室に移した。殺真菌製剤、施用および病気の評価は、実施例Aに記載された手順に従った。
コムギ植物(品種Yuma)を、温室において50%鉱質土壌/50%無土壌Metroミックス中の種から、第一葉が完全に出現するまで、1ポットあたり7〜10個の実生で成長させた。これらの植物には、殺真菌剤処理の24時間後にレプトスファエリアノドルム(Leptosphaeria nodorum)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で(20℃で暗霧チャンバーに1日、続いて点灯霧チャンバーに2日間)保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が発症するように、20℃に設定した温室に移した。殺真菌製剤、施用および病気の評価は、実施例Aに記載された手順に従った。
リンゴ実生(品種McIntosh)を無土壌Metroミックスにおいて1ポットあたり1個の植物で成長させた。広がっている2個の若葉を上部に有する(植物の下部の旧葉を刈り込んだ)実生を、試験に使用した。植物を、殺真菌剤処理の24時間後にベンツリアイナエクアリス(Venturia inaequalis)の胞子懸濁液で接種し、100%の相対湿度の22℃霧チャンバーに48時間保持し、次に病気が発症するように、20℃に設定した温室に移した。殺真菌製剤、施用および散布葉における病気の評価は、実施例Aに記載された手順に従った。
キュウリ実生(品種Bush Pickle)を、無土壌Metroミックスにおいて、1ポットあたり1個の植物で成長させ、12〜14日齢の時に試験に使用した。植物には、殺真菌剤処理の24時間後に胞子懸濁液を接種した。接種した後、植物を、病気が完全に発現するまで、20℃に設定した温室に維持した。殺真菌製剤、施用および散布葉における病気の評価は、実施例Aに記載された手順に従った。
テンサイ(品種HH88)を、無土壌Metroミックスで成長させ、試験する前に均一な植物サイズを維持するため、定期的に刈り込んだ。植物には、殺真菌剤処理の24時間後に胞子懸濁液を接種した。接種した植物を22℃の霧チャンバーに48時間保持し、次に病気の症状が完全に発現するまで、底を通気した透明なプラスチックフードの、24℃に設定した温室でインキュベートした。殺真菌製剤、施用および散布葉における病気の評価は、実施例Aに記載された手順に従った。
工業銘柄の材料をアセトンに溶解し、次にこれを、0.011%のTween20を含有する9容量の水と混合した。殺真菌剤溶液を、自動吹付散布機を使用してダイズ実生に流出するまで施用した。散布された植物を、全て、更なる取り扱いの前に風乾した。
オオムギ実生(品種Harrington)を、それぞれ8〜12個の植物を有するポットにより無土壌Metroミックスで繁殖させ、第一葉が完全に出現した時に試験に使用した。試験植物には、殺真菌剤処理の24時間後にリンコスポリウムセカリス(Rhynchosporium secalis)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の霧室に48時間保持した。次に植物を、病気が発症するように、20℃に設定した温室に移した。殺真菌製剤、施用および散布葉における病気の評価は、実施例Aに記載された手順に従った。
イネ実生(品種Japonica)を、それぞれ8〜14個の植物を有するポットにより無土壌Metroミックスで繁殖させ、12〜14日齢の時に試験に使用した。試験植物には、殺真菌剤処理の24時間後にピリクラリオリザ(Pyricularia oryzae)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の霧室に48時間保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が発症するように、24℃に設定した温室に移した。殺真菌製剤、施用および散布葉における病気の評価は、実施例Aに記載された手順に従った。
トマト植物(品種Outdoor Girl)を、それぞれ1個の植物を有するポットにより無土壌Metroミックスで繁殖させ、12〜14日齢の時に使用した。試験植物には、殺真菌剤処理の24時間後にアルテルナリアソラニ(Alternaria solani)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の霧室に48時間保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が発症するように、22℃の成長室に移した。殺真菌製剤、施用および散布葉における病気の評価は、実施例Aに記載された手順に従った。
キュウリ実生(品種Bush Pickle)を、それぞれ1個の植物を有するポットにより無土壌Metroミックスで繁殖させ、12〜14日齢の時に試験に使用した。試験植物には、殺真菌剤処理の24時間後にコレトトリクムラゲナリウム(Colletotrichum lagenarium)の水性胞子懸濁液を接種した。接種した後、植物を100%の相対湿度で22℃の霧室に48時間保持して、胞子を発芽させ、葉を感染させた。次に植物を、病気が発症するように、22℃に設定した成長室に移した。殺真菌製剤、施用および散布葉における病気の評価は、実施例Aに記載された手順に従った。
Claims (29)
- 式I:
Xは、水素またはC(O)R5であり;
Yは、水素、C(O)R5またはQであり;
Qは、下記式:
R1およびR11は、水素またはアルキルから独立して選択され、0、1つまたは複数のR8で置換されており、あるいは、R1およびR11は、一緒になって、3員〜6員の飽和または部分的に飽和されている炭素環または複素環を形成してもよく、0、1つまたは複数のR8で置換されており;
R2およびR12は、水素、アルキル、アリールまたはアルケニルから独立して選択され、それぞれ0、1つまたは複数のR8で置換されており;
R3は、水素、C2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R4は、アルキル、アリールまたはアシルから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R5は、アルコキシまたはベンジルオキシから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R6は、水素、アルコキシまたはハロから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R7は、水素、−C(O)R9または−CH2OC(O)R9から選択され;
R8は、水素、アルキル、アリール、アシル、ハロ、アルケニル、アルコキシまたはヘテロシクリルから選択され、それぞれ0、1つまたは複数のR10で置換されており;
R9は、アルキル、アルコキシまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されており;
R10は、水素、アルキル、アリール、アシル、ハロ、アルケニル、アルコキシまたはヘテロシクリルから選択される]の化合物。 - XおよびYが水素である、請求項1に記載の化合物。
- R1およびR11が、水素またはアルキルから独立して選択される、請求項2に記載の化合物。
- R2およびR12が、水素またはアルキルから独立して選択される、請求項2に記載の化合物。
- R3が、C2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項2に記載の化合物。
- R4が、アルキルまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項2に記載の化合物。
- R1およびR11が水素またはアルキルから独立して選択され、R2およびR12が水素またはアルキルから独立して選択され、R3がC2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されており、R4がアルキルまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項2に記載の化合物。
- XがC(O)R5であり、Yが水素である、請求項1に記載の化合物。
- R1およびR11が、水素またはアルキルから独立して選択される、請求項8に記載の化合物。
- R2およびR12が、水素またはアルキルから独立して選択される、請求項8に記載の化合物。
- R3が、C2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項8に記載の化合物。
- R4が、アルキルまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項8に記載の化合物。
- R1およびR11が水素またはアルキルから独立して選択され、R2およびR12が水素またはアルキルから独立して選択され、R3がC2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されており、R4がアルキルまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項8に記載の化合物。
- Xが水素であり、YがQである、請求項1に記載の化合物。
- R6がアルコキシである、請求項14に記載の化合物。
- R7が水素である、請求項15に記載の化合物。
- R1およびR11が、水素またはアルキルから独立して選択される、請求項16に記載の化合物。
- R2およびR12が、水素またはアルキルから独立して選択される、請求項16に記載の化合物。
- R3が、C2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項16に記載の化合物。
- R4が、アルキルまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項16に記載の化合物。
- R1およびR11が水素またはアルキルから独立して選択され、R2およびR12が水素またはアルキルから独立して選択され、R3がC2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されており、R4がアルキルまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項16に記載の化合物。
- R7が、−C(O)R9または−CH2OC(O)R9から選択される、請求項15に記載の化合物。
- R9がアルキルであり、0、1つまたは複数のR8で置換されている、請求項22に記載の化合物。
- R1およびR11が、水素またはアルキルから独立して選択される、請求項23に記載の化合物。
- R2およびR12が、水素またはアルキルから独立して選択される、請求項23に記載の化合物。
- R3が、アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項23に記載の化合物。
- R4が、アルキルまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項23に記載の化合物。
- R1およびR11が水素またはアルキルから独立して選択され、R2およびR12が水素またはアルキルから独立して選択され、R3がC2〜C6アルキル、アリールまたはアルケニルから選択され、それぞれ0、1つまたは複数のR8で置換されており、R4がアルキルまたはアリールから選択され、それぞれ0、1つまたは複数のR8で置換されている、請求項23に記載の化合物。
- R9が、−CH3、−CH2OCH2CH3、−CH2CH2OCH3、−CH(CH3)2、−CH2CH2CH2CH3、−シクロプロピルから選択される、請求項28に記載の化合物。
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