EA022930B1 - 5-фтор-2-оксопиримидин-1(2h)-карбоксилатные производные - Google Patents

Info

Publication number

EA022930B1

EA022930B1 EA201270255A EA201270255A EA022930B1 EA 022930 B1 EA022930 B1 EA 022930B1 EA 201270255 A EA201270255 A EA 201270255A EA 201270255 A EA201270255 A EA 201270255A EA 022930 B1 EA022930 B1 EA 022930B1

Authority

EA

Eurasian Patent Office

Prior art keywords

herbicides

compounds

insecticides

alkyl

plant

Prior art date

2009-08-07

Links

• Espacenet
• Global Dossier
• Discuss

• HRHMGDXHJNYKSR-UHFFFAOYSA-N OC(=O)N1C=C(F)C=NC1=O Chemical class OC(=O)N1C=C(F)C=NC1=O HRHMGDXHJNYKSR-UHFFFAOYSA-N 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 78
• 239000000203 mixture Substances 0.000 claims description 49
• 241000196324 Embryophyta Species 0.000 claims description 32
• 238000000034 method Methods 0.000 claims description 13
• 244000053095 fungal pathogen Species 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 241000209140 Triticum Species 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 239000002689 soil Substances 0.000 claims description 5
• 235000021307 Triticum Nutrition 0.000 claims description 4
• 230000015572 biosynthetic process Effects 0.000 claims description 4
• 244000105624 Arachis hypogaea Species 0.000 claims description 3
• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 240000008790 Musa x paradisiaca Species 0.000 claims description 3
• 235000021536 Sugar beet Nutrition 0.000 claims description 3
• 235000021015 bananas Nutrition 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 229910052739 hydrogen Inorganic materials 0.000 claims description 3
• 235000020232 peanut Nutrition 0.000 claims description 3
• 230000008635 plant growth Effects 0.000 claims description 3
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• 206010039509 Scab Diseases 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 210000000981 epithelium Anatomy 0.000 claims 1
• 230000002538 fungal effect Effects 0.000 claims 1
• 244000000010 microbial pathogen Species 0.000 claims 1
• 239000000417 fungicide Substances 0.000 abstract description 17
• -1 isobutenyl Chemical group 0.000 description 126
• 239000004009 herbicide Substances 0.000 description 74
• 239000002917 insecticide Substances 0.000 description 59
• 239000007787 solid Substances 0.000 description 35
• 239000000126 substance Substances 0.000 description 26
• 230000000855 fungicidal effect Effects 0.000 description 14
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 12
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 11
• 239000000839 emulsion Substances 0.000 description 10
• 239000007788 liquid Substances 0.000 description 10
• 239000004094 surface-active agent Substances 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 201000010099 disease Diseases 0.000 description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 238000005481 NMR spectroscopy Methods 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 238000002844 melting Methods 0.000 description 8
• 230000008018 melting Effects 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
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• 239000003995 emulsifying agent Substances 0.000 description 7
• XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 7
• 230000000361 pesticidal effect Effects 0.000 description 7
• 150000003839 salts Chemical class 0.000 description 7
• 241000233866 Fungi Species 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 239000004495 emulsifiable concentrate Substances 0.000 description 6
• 229940102396 methyl bromide Drugs 0.000 description 6
• 239000000575 pesticide Substances 0.000 description 6
• 239000007900 aqueous suspension Substances 0.000 description 5
• 239000003986 organophosphate insecticide Substances 0.000 description 5
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• 239000002169 Metam Substances 0.000 description 4
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• 239000002253 acid Substances 0.000 description 4
• 125000000217 alkyl group Chemical group 0.000 description 4
• DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 4
• 125000003118 aryl group Chemical group 0.000 description 4
• 229910052791 calcium Inorganic materials 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 239000012141 concentrate Substances 0.000 description 4
• 238000002156 mixing 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
• 239000000843 powder Substances 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
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• 239000005909 Kieselgur Substances 0.000 description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• 241001533598 Septoria Species 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 125000001931 aliphatic group Chemical group 0.000 description 3
• 230000003042 antagnostic effect Effects 0.000 description 3
• 239000008365 aqueous carrier Substances 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• SQPWSXACIHOPBV-UHFFFAOYSA-N benzyl 4-amino-5-fluoro-2-oxopyrimidine-1-carboxylate Chemical compound C1=C(F)C(N)=NC(=O)N1C(=O)OCC1=CC=CC=C1 SQPWSXACIHOPBV-UHFFFAOYSA-N 0.000 description 3
• 229910021538 borax Inorganic materials 0.000 description 3
• 239000004202 carbamide Substances 0.000 description 3
• 235000013877 carbamide Nutrition 0.000 description 3
• 238000004587 chromatography analysis 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
• 235000014113 dietary fatty acids Nutrition 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
• 238000000227 grinding Methods 0.000 description 3
• 230000002363 herbicidal effect Effects 0.000 description 3
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 239000002949 juvenile hormone Substances 0.000 description 3
• UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 3
• CJEOHCPDDTWSQV-UHFFFAOYSA-N o-phenyl 4-amino-5-fluoro-2-oxopyrimidine-1-carbothioate Chemical compound C1=C(F)C(N)=NC(=O)N1C(=S)OC1=CC=CC=C1 CJEOHCPDDTWSQV-UHFFFAOYSA-N 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 235000019198 oils Nutrition 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
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• 239000012071 phase Substances 0.000 description 3
• VFVNRAHJGYYCTH-UHFFFAOYSA-N phenyl 4-amino-5-fluoro-2-oxopyrimidine-1-carboxylate Chemical compound C1=C(F)C(N)=NC(=O)N1C(=O)OC1=CC=CC=C1 VFVNRAHJGYYCTH-UHFFFAOYSA-N 0.000 description 3
• 238000002360 preparation method Methods 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
• CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 2
• 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
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 2
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• PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 2
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• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
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• 150000001298 alcohols Chemical class 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
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• NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 description 2
• 125000000129 anionic group Chemical group 0.000 description 2
• 230000000844 anti-bacterial effect Effects 0.000 description 2
• 229910052785 arsenic Inorganic materials 0.000 description 2
• RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
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• 229960000892 attapulgite Drugs 0.000 description 2
• 239000003899 bactericide agent Substances 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
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