UA117123C2 - Похідні 1-(заміщений бензоїл)-5-фтор-4-іміно-3-метил-3,4-дигідропіримідин-2(1h)-ону - Google Patents

Info

Publication number

UA117123C2

UA117123C2 UAA201507549A UAA201507549A UA117123C2 UA 117123 C2 UA117123 C2 UA 117123C2 UA A201507549 A UAA201507549 A UA A201507549A UA A201507549 A UAA201507549 A UA A201507549A UA 117123 C2 UA117123 C2 UA 117123C2

Authority

UA

Ukraine

Prior art keywords

plant

compounds

compound according

methyl

compound

Prior art date

2012-12-28

Links

• Espacenet
• Global Dossier
• Discuss

• -1 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1h)-one Chemical class 0.000 title description 162
• 150000001875 compounds Chemical class 0.000 claims abstract description 121
• 230000000855 fungicidal effect Effects 0.000 claims abstract description 17
• 239000000203 mixture Substances 0.000 claims description 60
• 238000000034 method Methods 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 230000002538 fungal effect Effects 0.000 claims description 12
• 239000002689 soil Substances 0.000 claims description 10
• 208000031888 Mycoses Diseases 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 230000003287 optical effect Effects 0.000 claims description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
• 238000012545 processing Methods 0.000 claims description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
• 239000012876 carrier material Substances 0.000 claims 1
• 229910052801 chlorine Inorganic materials 0.000 claims 1
• 239000000460 chlorine Substances 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 239000000417 fungicide Substances 0.000 abstract description 20
• 241000233866 Fungi Species 0.000 abstract description 11
• 241000235349 Ascomycota Species 0.000 abstract description 2
• 241000221198 Basidiomycota Species 0.000 abstract description 2
• 241000233654 Oomycetes Species 0.000 abstract description 2
• 238000011160 research Methods 0.000 abstract description 2
• 241000196324 Embryophyta Species 0.000 description 42
• 125000001424 substituent group Chemical group 0.000 description 19
• 239000007787 solid Substances 0.000 description 12
• 201000010099 disease Diseases 0.000 description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
• 239000000839 emulsion Substances 0.000 description 10
• 239000007788 liquid Substances 0.000 description 10
• 239000003995 emulsifying agent Substances 0.000 description 9
• 244000005700 microbiome Species 0.000 description 9
• 239000004094 surface-active agent Substances 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• 125000000217 alkyl group Chemical group 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 239000004009 herbicide Substances 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• 150000001412 amines Chemical class 0.000 description 7
• 239000012141 concentrate Substances 0.000 description 7
• 235000008504 concentrate Nutrition 0.000 description 7
• 239000000575 pesticide Substances 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-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
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 6
• 239000003921 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
• 230000000361 pesticidal effect Effects 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• MTOLUWFRBZWWOR-UHFFFAOYSA-N 6-amino-5-fluoro-1-methylpyrimidin-2-one Chemical compound CN1C(N)=C(F)C=NC1=O MTOLUWFRBZWWOR-UHFFFAOYSA-N 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 239000007900 aqueous suspension Substances 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 235000019198 oils Nutrition 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 4
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
• 125000003342 alkenyl group Chemical group 0.000 description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
• 125000005842 heteroatom Chemical group 0.000 description 4
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 4
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 239000002480 mineral oil Substances 0.000 description 4
• 238000002156 mixing Methods 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
• 235000015112 vegetable and seed oil Nutrition 0.000 description 4
• LJLWZAAOVUNDHM-UHFFFAOYSA-N 4-amino-5-fluoro-1-(4-methoxyphenyl)sulfonylpyrimidin-2-one Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C(=O)NC(=N)C(F)=C1 LJLWZAAOVUNDHM-UHFFFAOYSA-N 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
• 241000209140 Triticum Species 0.000 description 3
• 239000002253 acid Substances 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 150000001298 alcohols Chemical class 0.000 description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 description 3
• 125000004429 atom Chemical group 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
• 239000006013 carbendazim Substances 0.000 description 3
• JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 3
• 239000010949 copper Substances 0.000 description 3
• 229910052802 copper Inorganic materials 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
• 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
• 230000002363 herbicidal effect Effects 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 239000002917 insecticide Substances 0.000 description 3
• 229940102396 methyl bromide Drugs 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 229920000847 nonoxynol Polymers 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000004328 sodium tetraborate Substances 0.000 description 3
• 235000010339 sodium tetraborate Nutrition 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 230000002195 synergetic effect Effects 0.000 description 3
• NRHFWOJROOQKBK-UHFFFAOYSA-N triphenyltin;hydrate Chemical compound O.C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 NRHFWOJROOQKBK-UHFFFAOYSA-N 0.000 description 3
• 239000008158 vegetable oil Substances 0.000 description 3
• 239000008096 xylene Substances 0.000 description 3
• KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
• RLLPVAHGXHCWKJ-MJGOQNOKSA-N (3-phenoxyphenyl)methyl (1r,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-MJGOQNOKSA-N 0.000 description 2
• QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
• KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
• TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 2
• PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
• YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
• IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 2
• QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
• HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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• CPVQJXZBSGXTGJ-UHFFFAOYSA-N Juvenile hormone II Natural products CCC1(C)OC1CCC(C)=CCCC(C)=CC(=O)OC CPVQJXZBSGXTGJ-UHFFFAOYSA-N 0.000 description 2
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• 125000003545 alkoxy group Chemical group 0.000 description 2
• 125000003282 alkyl amino group Chemical group 0.000 description 2
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