JP5735510B2 - Ｎ１−置換−５−フルオロ−２−オキソピリミジノン−１（２ｈ）−カルボキサミド誘導体 - Google Patents

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Publication number

JP5735510B2

JP5735510B2 JP2012523955A JP2012523955A JP5735510B2 JP 5735510 B2 JP5735510 B2 JP 5735510B2 JP 2012523955 A JP2012523955 A JP 2012523955A JP 2012523955 A JP2012523955 A JP 2012523955A JP 5735510 B2 JP5735510 B2 JP 5735510B2

Authority

JP

Japan

Prior art keywords

optionally substituted

benzyl

alkyl

phenyl

ring system

Prior art date

2009-08-07

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
• -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 129
• 150000001875 compounds Chemical class 0.000 claims description 91
• 239000000203 mixture Substances 0.000 claims description 45
• 241000196324 Embryophyta Species 0.000 claims description 39
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
• 125000004122 cyclic group Chemical group 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
• 230000000855 fungicidal effect Effects 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 235000010290 biphenyl Nutrition 0.000 claims description 11
• 239000004305 biphenyl Substances 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 10
• 125000001624 naphthyl group Chemical class 0.000 claims description 10
• 230000002538 fungal effect Effects 0.000 claims description 7
• 241001360088 Zymoseptoria tritici Species 0.000 claims description 6
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 239000002689 soil Substances 0.000 claims description 5
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 241000209140 Triticum Species 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 235000021307 Triticum Nutrition 0.000 claims description 3
• 239000012876 carrier material Substances 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 244000053095 fungal pathogen Species 0.000 claims description 3
• 230000008635 plant growth Effects 0.000 claims description 3
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 2
• 235000017060 Arachis glabrata Nutrition 0.000 claims description 2
• 244000105624 Arachis hypogaea Species 0.000 claims description 2
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• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 2
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• 235000021536 Sugar beet Nutrition 0.000 claims description 2
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• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001424 substituent group Chemical group 0.000 description 16
• RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 16
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 10
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• 229910052731 fluorine Inorganic materials 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 150000003839 salts Chemical class 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
• 230000000694 effects Effects 0.000 description 6
• 230000001804 emulsifying effect Effects 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 239000000463 material 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
• 239000000243 solution Substances 0.000 description 6
• BZWWGSMLGHUGFH-VCHYOVAHSA-N C1=C(F)C(/N=C/N(C)C)=NC(=O)N1C(=O)NCC1=CC=CC=C1 Chemical compound C1=C(F)C(/N=C/N(C)C)=NC(=O)N1C(=O)NCC1=CC=CC=C1 BZWWGSMLGHUGFH-VCHYOVAHSA-N 0.000 description 5
• 241000233866 Fungi Species 0.000 description 5
• XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 5
• DBTBMPRAGWMFKW-UHFFFAOYSA-N n'-(5-fluoro-2-oxo-1h-pyrimidin-6-yl)-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=NC(O)=NC=C1F DBTBMPRAGWMFKW-UHFFFAOYSA-N 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 239000002562 thickening agent Substances 0.000 description 5
• FISJFONSXZUWCN-UHFFFAOYSA-N 4-amino-5-fluoro-2-oxo-n-phenylpyrimidine-1-carboxamide Chemical compound C1=C(F)C(N)=NC(=O)N1C(=O)NC1=CC=CC=C1 FISJFONSXZUWCN-UHFFFAOYSA-N 0.000 description 4
• UTCMHPXMCQNNED-UHFFFAOYSA-N 4-amino-n-cyclopentyl-5-fluoro-2-oxopyrimidine-1-carboxamide Chemical compound C1=C(F)C(N)=NC(=O)N1C(=O)NC1CCCC1 UTCMHPXMCQNNED-UHFFFAOYSA-N 0.000 description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
• 239000002169 Metam Substances 0.000 description 4
• LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 239000002671 adjuvant Substances 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
• 238000004587 chromatography analysis Methods 0.000 description 4
• RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 4
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
• 230000003032 phytopathogenic effect Effects 0.000 description 4
• ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 3
• MUCFYENVTMQPJP-UHFFFAOYSA-N 4-(dimethylaminomethylideneamino)-5-fluoro-2-oxo-n-propylpyrimidine-1-carboxamide Chemical compound CCCNC(=O)N1C=C(F)C(N=CN(C)C)=NC1=O MUCFYENVTMQPJP-UHFFFAOYSA-N 0.000 description 3
• RZKMTNNEGSFXQY-UHFFFAOYSA-N 4-acetamido-n-ethyl-5-fluoro-2-oxopyrimidine-1-carboxamide Chemical compound CCNC(=O)N1C=C(F)C(NC(C)=O)=NC1=O RZKMTNNEGSFXQY-UHFFFAOYSA-N 0.000 description 3
• KJWYPVZYTWVDLI-UHFFFAOYSA-N 4-amino-5-fluoro-2-oxo-n-pentylpyrimidine-1-carboxamide Chemical compound CCCCCNC(=O)N1C=C(F)C(N)=NC1=O KJWYPVZYTWVDLI-UHFFFAOYSA-N 0.000 description 3
• IHBJHJHXMNWLAO-UHFFFAOYSA-N 4-amino-n-(3-chlorophenyl)-5-fluoro-2-oxopyrimidine-1-carboxamide Chemical compound C1=C(F)C(N)=NC(=O)N1C(=O)NC1=CC=CC(Cl)=C1 IHBJHJHXMNWLAO-UHFFFAOYSA-N 0.000 description 3
• SPUJYTLTBSLMCI-UHFFFAOYSA-N 5-fluoro-4-[(2-fluorophenyl)methylamino]-2-oxo-n-phenylpyrimidine-1-carboxamide Chemical compound FC1=CC=CC=C1CNC1=NC(=O)N(C(=O)NC=2C=CC=CC=2)C=C1F SPUJYTLTBSLMCI-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• 239000005909 Kieselgur Substances 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
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• 125000003342 alkenyl group Chemical group 0.000 description 3
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