HUE027390T2 - N1-substituted-5-fluoro-2-oxopyrimidinone-1 (2H) -carboxamide derivatives - Google Patents

Info

Publication number

HUE027390T2

HUE027390T2 HUE10807175A HUE10807175A HUE027390T2 HU E027390 T2 HUE027390 T2 HU E027390T2 HU E10807175 A HUE10807175 A HU E10807175A HU E10807175 A HUE10807175 A HU E10807175A HU E027390 T2 HUE027390 T2 HU E027390T2

Authority

HU

Hungary

Prior art keywords

eket

áta

ring

compounds

herbicides

Prior art date

2009-08-07

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• 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
• -1 CrQKKkcarbonyl Chemical group 0.000 claims description 62
• 239000000203 mixture Substances 0.000 claims description 54
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 51
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 125000004122 cyclic group Chemical group 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 239000002904 solvent Substances 0.000 claims description 13
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 241000233866 Fungi Species 0.000 claims description 6
• 239000002689 soil Substances 0.000 claims description 6
• 239000000843 powder Substances 0.000 claims description 4
• 244000052769 pathogen Species 0.000 claims description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
• 239000011230 binding agent Substances 0.000 claims 2
• 101150114104 CROT gene Proteins 0.000 claims 1
• 101100460310 Drosophila melanogaster hoip gene Proteins 0.000 claims 1
• LTGPFZWZZNUIIK-LURJTMIESA-N Lysol Chemical compound NCCCC[C@H](N)CO LTGPFZWZZNUIIK-LURJTMIESA-N 0.000 claims 1
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 1
• 235000008180 Piper betle Nutrition 0.000 claims 1
• 240000008154 Piper betle Species 0.000 claims 1
• 235000019892 Stellar Nutrition 0.000 claims 1
• 206010000269 abscess Diseases 0.000 claims 1
• 239000002253 acid Substances 0.000 claims 1
• 235000019788 craving Nutrition 0.000 claims 1
• 150000004820 halides Chemical class 0.000 claims 1
• 229910052742 iron Inorganic materials 0.000 claims 1
• 150000002642 lithium compounds Chemical class 0.000 claims 1
• 239000003973 paint Substances 0.000 claims 1
• 230000001717 pathogenic effect Effects 0.000 claims 1
• 108090000623 proteins and genes Proteins 0.000 claims 1
• 125000003944 tolyl group Chemical group 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 91
• 239000004009 herbicide Substances 0.000 description 71
• 239000002917 insecticide Substances 0.000 description 45
• 241000196324 Embryophyta Species 0.000 description 39
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 32
• 238000009472 formulation Methods 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
• 239000004305 biphenyl Substances 0.000 description 16
• 235000010290 biphenyl Nutrition 0.000 description 16
• 230000000855 fungicidal effect Effects 0.000 description 16
• 239000003986 organophosphate insecticide Substances 0.000 description 16
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 15
• 125000001624 naphthyl group Chemical group 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 14
• 125000001424 substituent group Chemical group 0.000 description 14
• 125000003545 alkoxy group Chemical group 0.000 description 13
• 239000000417 fungicide Substances 0.000 description 13
• 125000001188 haloalkyl group Chemical group 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
• 238000005160 1H NMR spectroscopy Methods 0.000 description 11
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 11
• 238000000034 method Methods 0.000 description 11
• 239000000839 emulsion Substances 0.000 description 10
• 235000020004 porter Nutrition 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 241001360088 Zymoseptoria tritici Species 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 239000004094 surface-active agent Substances 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
• 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 8
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 150000003839 salts Chemical class 0.000 description 8
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• 150000002367 halogens Chemical group 0.000 description 7
• 230000000361 pesticidal effect Effects 0.000 description 7
• 239000000243 solution Substances 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
• 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
• 125000004414 alkyl thio group Chemical group 0.000 description 6
• 239000004495 emulsifiable concentrate Substances 0.000 description 6
• XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical class NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 6
• 230000002538 fungal effect Effects 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000000575 pesticide Substances 0.000 description 6
• 244000098338 Triticum aestivum Species 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
• 125000004093 cyano group Chemical group *C#N 0.000 description 5
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
• 125000004438 haloalkoxy group Chemical group 0.000 description 5
• 125000004995 haloalkylthio group Chemical group 0.000 description 5
• 239000000463 material Substances 0.000 description 5
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• 238000011282 treatment Methods 0.000 description 5
• 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
• 241001281801 Mycosphaerella arachidis Species 0.000 description 4
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
• 241001329956 Nothopassalora personata Species 0.000 description 4
• 241000087479 Pseudocercospora fijiensis Species 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
• 125000003282 alkyl amino group Chemical group 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
• IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
• 230000003032 phytopathogenic effect Effects 0.000 description 4
• 230000002265 prevention 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
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 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
• 244000105624 Arachis hypogaea Species 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• 241000530549 Cercospora beticola Species 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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• 241000228452 Venturia inaequalis Species 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 230000003042 antagnostic effect Effects 0.000 description 3
• 239000008135 aqueous vehicle Substances 0.000 description 3
• 125000003118 aryl group Chemical group 0.000 description 3
• 229910021538 borax Inorganic materials 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
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• 239000012876 carrier material Substances 0.000 description 3
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• 238000001816 cooling 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
• 125000004663 dialkyl amino group Chemical group 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 Chemical compound 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
• 244000053095 fungal pathogen Species 0.000 description 3
• 230000002363 herbicidal effect Effects 0.000 description 3
• RBJAKRVCYLJDPZ-UHFFFAOYSA-N hexyl 2-[5-(4-bromophenoxy)-2-nitrophenoxy]propanoate Chemical compound C1=C([N+]([O-])=O)C(OC(C)C(=O)OCCCCCC)=CC(OC=2C=CC(Br)=CC=2)=C1 RBJAKRVCYLJDPZ-UHFFFAOYSA-N 0.000 description 3
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• 239000002609 medium Substances 0.000 description 3
• LFDDUUFFHPNIPZ-UHFFFAOYSA-N methyl n-[4-[[2-(4-chloro-2-methylphenoxy)acetyl]amino]phenyl]sulfonylcarbamate Chemical compound C1=CC(S(=O)(=O)NC(=O)OC)=CC=C1NC(=O)COC1=CC=C(Cl)C=C1C LFDDUUFFHPNIPZ-UHFFFAOYSA-N 0.000 description 3
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• JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 3
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