JP6336480B2 - １−（置換ベンゾイル）−５−フルオロ−４−イミノ−３−メチル−３，４−ジヒドロピリミジン−２（１ｈ）−オンの誘導体 - Google Patents
１−（置換ベンゾイル）−５−フルオロ−４−イミノ−３−メチル−３，４−ジヒドロピリミジン−２（１ｈ）−オンの誘導体 Download PDFInfo
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- JP6336480B2 JP6336480B2 JP2015550733A JP2015550733A JP6336480B2 JP 6336480 B2 JP6336480 B2 JP 6336480B2 JP 2015550733 A JP2015550733 A JP 2015550733A JP 2015550733 A JP2015550733 A JP 2015550733A JP 6336480 B2 JP6336480 B2 JP 6336480B2
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- phenyl
- methyl
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- -1 1- (substituted benzoyl) -5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2 (1H) -one Chemical class 0.000 title claims description 183
- 150000001875 compounds Chemical class 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 230000000855 fungicidal effect Effects 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 8
- 241001360088 Zymoseptoria tritici Species 0.000 claims description 7
- 230000002538 fungal effect Effects 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 208000031888 Mycoses Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 241000894007 species Species 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 238000009313 farming Methods 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 41
- 238000009472 formulation Methods 0.000 description 20
- 239000000839 emulsion Substances 0.000 description 17
- 239000000417 fungicide Substances 0.000 description 17
- 239000000575 pesticide Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000007787 solid Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241000233866 Fungi Species 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000843 powder 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 235000019198 oils Nutrition 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 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 4
- 239000002169 Metam Substances 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 239000000243 solution 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
- MGBHNKWOVQDGIB-UHFFFAOYSA-N 5-fluoro-4-imino-1-(4-methoxyphenyl)sulfonyl-3-methylpyrimidin-2-one Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C(=O)N(C)C(=N)C(F)=C1 MGBHNKWOVQDGIB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-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
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000008135 aqueous vehicle Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 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
- 239000012876 carrier material Substances 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
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 229960002523 mercuric chloride Drugs 0.000 description 3
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
- 229940102396 methyl bromide Drugs 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 150000008117 polysulfides Polymers 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
- 239000000126 substance Substances 0.000 description 3
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-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
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 2
- WRGKWWRFSUGDPX-HUUCEWRRSA-N (1R,2R)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)cycloheptan-1-ol Chemical compound N1([C@@H]2CCCCC[C@@]2(O)C=2C=CC(Cl)=CC=2)C=NC=N1 WRGKWWRFSUGDPX-HUUCEWRRSA-N 0.000 description 2
- OTKXWJHPGBRXCR-UHFFFAOYSA-N (2-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1Cl OTKXWJHPGBRXCR-UHFFFAOYSA-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
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- 239000005631 2,4-Dichlorophenoxyacetic acid Chemical class 0.000 description 2
- MPUUPHNZUMFOSI-UHFFFAOYSA-N 2-(benzylamino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1NCC1=CC=CC=C1 MPUUPHNZUMFOSI-UHFFFAOYSA-N 0.000 description 2
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
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- HBLSGPQATABNRY-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-n-methyl-4-n,5-n-bis(trifluoromethyl)-1,3-thiazolidine-2,4,5-triimine Chemical compound CN=C1SC(=NC(F)(F)F)C(=NC(F)(F)F)N1C1=CC=C(Cl)C=C1 HBLSGPQATABNRY-UHFFFAOYSA-N 0.000 description 2
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- 239000005562 Glyphosate Substances 0.000 description 2
- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 description 2
- QVJMXSGZTCGLHZ-VWADHSNXSA-N Juvenile hormone III Natural products O=C(OC)/C=C(\CC/C=C(\CC[C@H]1C(C)(C)O1)/C)/C QVJMXSGZTCGLHZ-VWADHSNXSA-N 0.000 description 2
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- KJHOZAZQWVKILO-UHFFFAOYSA-N N-(diaminomethylidene)-4-morpholinecarboximidamide Chemical compound NC(N)=NC(=N)N1CCOCC1 KJHOZAZQWVKILO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- CVRALZAYCYJELZ-UHFFFAOYSA-N O-(4-bromo-2,5-dichlorophenyl) O-methyl phenylphosphonothioate Chemical compound C=1C=CC=CC=1P(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl CVRALZAYCYJELZ-UHFFFAOYSA-N 0.000 description 2
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- ITVQAKZNYJEWKS-UHFFFAOYSA-N Profluralin Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CCC)CC1CC1 ITVQAKZNYJEWKS-UHFFFAOYSA-N 0.000 description 2
- 241000087479 Pseudocercospora fijiensis Species 0.000 description 2
- CDEWHBGYSWJUFP-UHFFFAOYSA-N Quinacetol sulfate Chemical compound OS(O)(=O)=O.C1=CC=C2C(C(=O)C)=CC=C(O)C2=N1.C1=CC=C2C(C(=O)C)=CC=C(O)C2=N1 CDEWHBGYSWJUFP-UHFFFAOYSA-N 0.000 description 2
- OBLNWSCLAYSJJR-UHFFFAOYSA-N Quinoclamin Chemical compound C1=CC=C2C(=O)C(N)=C(Cl)C(=O)C2=C1 OBLNWSCLAYSJJR-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- KSQXVLVXUFHGJQ-UHFFFAOYSA-M Sodium ortho-phenylphenate Chemical compound [Na+].[O-]C1=CC=CC=C1C1=CC=CC=C1 KSQXVLVXUFHGJQ-UHFFFAOYSA-M 0.000 description 2
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- PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 2
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 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
- 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
- 125000004665 trialkylsilyl group Chemical group 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
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-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
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-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
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-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
- 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
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261747128P | 2012-12-28 | 2012-12-28 | |
| US61/747,128 | 2012-12-28 | ||
| PCT/US2013/077478 WO2014105821A1 (en) | 2012-12-28 | 2013-12-23 | 1-(substituted-benzoyl)-5-fluoro-4-imino-3-methyl-3,4-dihydropyrimidin-2(1h)-one derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016509589A JP2016509589A (ja) | 2016-03-31 |
| JP2016509589A5 JP2016509589A5 (enExample) | 2017-02-09 |
| JP6336480B2 true JP6336480B2 (ja) | 2018-06-06 |
Family
ID=51022027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015550733A Active JP6336480B2 (ja) | 2012-12-28 | 2013-12-23 | １−（置換ベンゾイル）−５−フルオロ−４−イミノ−３−メチル−３，４−ジヒドロピリミジン−２（１ｈ）−オンの誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9271497B2 (enExample) |
| EP (2) | EP2945635A4 (enExample) |
| JP (1) | JP6336480B2 (enExample) |
| KR (1) | KR20150103095A (enExample) |
| CN (1) | CN104994859B (enExample) |
| AU (1) | AU2013370470B2 (enExample) |
| BR (1) | BR102013033840B1 (enExample) |
| CA (1) | CA2893776A1 (enExample) |
| CL (1) | CL2015001861A1 (enExample) |
| EC (1) | ECSP15032926A (enExample) |
| GT (1) | GT201500196A (enExample) |
| HK (1) | HK1214518A1 (enExample) |
| IL (1) | IL239562B (enExample) |
| MX (1) | MX2015008443A (enExample) |
| RU (2) | RU2018118951A (enExample) |
| UA (1) | UA117123C2 (enExample) |
| WO (1) | WO2014105821A1 (enExample) |
| ZA (1) | ZA201504195B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6352302B2 (ja) | 2012-12-28 | 2018-07-04 | ダウ アグロサイエンシィズ エルエルシー | 穀類における真菌防除のための相乗性殺真菌性混合物 |
| KR20150103096A (ko) | 2012-12-28 | 2015-09-09 | 다우 아그로사이언시즈 엘엘씨 | N-(치환된)-5-플루오로-4-이미노-3-메틸-2-옥소-3,4-디히드로피리미딘-1(2h)-카르복실레이트 유도체 |
| MX2015008444A (es) | 2012-12-28 | 2015-09-23 | Dow Agrosciences Llc | Derivados de n-(sustituido)-5-flouro-4-imino-3-metil-2-oxo-3,4-dih idropirimidin-1 (2h)-carboximida. |
| CA2894553C (en) | 2012-12-31 | 2021-03-02 | Dow Agrosciences Llc | 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1h)-one derivatives as fungicides |
| EA030056B1 (ru) | 2013-12-31 | 2018-06-29 | Адама Мактешим Лтд. | Синергетические фунгицидные смеси и синергетические фунгицидные композиции для борьбы с грибами |
| SG11201605377VA (en) | 2013-12-31 | 2016-08-30 | Adama Makhteshim Ltd | 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation |
| UA121561C2 (uk) | 2014-12-30 | 2020-06-25 | Дау Аґросаєнсиз Елелсі | Застосування сполук аміду як фунгіцидів |
| AU2015374380B2 (en) | 2014-12-30 | 2018-01-18 | Dow Agrosciences Llc | Use of picolinamides as fungicides |
| MX2017008418A (es) | 2014-12-30 | 2017-09-28 | Dow Agrosciences Llc | Picolinamidas con actividad fungicida. |
| EP3240413B1 (en) | 2014-12-30 | 2020-05-13 | Dow Agrosciences LLC | Picolinamide compounds with fungicidal activity |
| WO2016109302A1 (en) | 2014-12-30 | 2016-07-07 | Dow Agrosciences Llc | Picolinamide compounds with fungicidal activity |
| TWI774761B (zh) | 2017-05-02 | 2022-08-21 | 美商科迪華農業科技有限責任公司 | 用於穀物中的真菌防治之協同性混合物 |
| CN110996665B (zh) | 2017-05-02 | 2021-10-26 | 陶氏益农公司 | 无环吡啶酰胺化合物作为针对草坪草上的真菌病害的杀真菌剂的用途 |
| TW201842851A (zh) | 2017-05-02 | 2018-12-16 | 美商陶氏農業科學公司 | 用於穀類中的真菌防治之協同性混合物 |
| CN107192785B (zh) * | 2017-06-09 | 2019-10-15 | 西南大学 | 放线菌jy-22抗真菌成分分离方法及其在复配剂中的应用 |
| IL309708B1 (en) | 2017-07-17 | 2025-10-01 | Adama Makhteshim Ltd | Polymorphs of 5-fluoro-4-imino-3-methyl-1-tosyl-4,3-dihydropyrimidin-2-one |
| BR102019004480B1 (pt) | 2018-03-08 | 2023-03-28 | Dow Agrosciences Llc | Picolinamidas como fungicidas |
| US11639334B2 (en) | 2018-10-15 | 2023-05-02 | Corteva Agriscience Llc | Methods for synthesis of oxypicolinamides |
| CR20210270A (es) | 2018-11-05 | 2021-07-20 | Adama Makhteshim Ltd | Mezclas y composiciones que comprenden 5-fluoro-4-imino-3-metil-1-tosil-3,4-dihidropirimidin-2-ona, y métodos de uso de los mismos |
| EP4034529A1 (en) | 2019-09-23 | 2022-08-03 | Adama Makhteshim Ltd. | Process for preparing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine -(1h)-one |
| EP4044811A4 (en) | 2019-10-18 | 2023-09-27 | Corteva Agriscience LLC | METHOD FOR SYNTHESIS OF PICOLINAMIDS |
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| CH421973A (de) | 1962-05-01 | 1966-10-15 | Hoffmann La Roche | Verfahren zur Herstellung eines Cytosin-Derivates |
| US3309359A (en) | 1965-10-22 | 1967-03-14 | Hoffmann La Roche | N-mono-acyl-5-fluorocytosine derivatives and process |
| US3368938A (en) | 1966-01-13 | 1968-02-13 | Hoffmann La Roche | Controlling fungi with 5-fluorocytosine |
| US3868373A (en) | 1970-01-27 | 1975-02-25 | Hoffmann La Roche | 4-Amino-5-fluoro-2-tri(lower alkyl) silyloxypyrimidines |
| CH579057A5 (enExample) | 1973-09-07 | 1976-08-31 | Hoffmann La Roche | |
| FR2530636A1 (fr) | 1982-07-23 | 1984-01-27 | Rhone Poulenc Agrochimie | Nouveaux derives de la tetrahydro-2,3,6,7 5h-thiazolo (3,2-a) pyrimidine, leur preparation et leur utilisation comme herbicides |
| EP0139613A1 (de) | 1983-08-29 | 1985-05-02 | Ciba-Geigy Ag | N-(2-Nitrophenyl)-4-aminopyrimidin-Derivate, deren Herstellung und Verwendung |
| US4845081A (en) | 1984-10-18 | 1989-07-04 | University Of Florida | Aminomethyl derivatives of biologically active substances, and enhanced delivery thereof across topical membranes |
| EP0332579B1 (de) | 1988-03-09 | 1994-08-10 | Ciba-Geigy Ag | Mittel zum Schutz von Pflanzen gegen Krankheiten |
| DE3821711A1 (de) | 1988-06-28 | 1990-02-08 | Bayer Ag | Thiazolopyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| JP3109012B2 (ja) | 1992-06-18 | 2000-11-13 | クミアイ化学工業株式会社 | チアゾロ［５，４−ｄ］ピリミジン誘導体及び農園芸用殺菌剤 |
| JP3217191B2 (ja) | 1992-07-16 | 2001-10-09 | ビーエーエスエフ アクチェンゲゼルシャフト | ヘテロ芳香族化合物およびこれを含有する植物保護剤 |
| JP4010563B2 (ja) | 1995-07-05 | 2007-11-21 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 殺菌・殺カビ性のピリミジノン類 |
| CN1213373A (zh) | 1996-03-11 | 1999-04-07 | 诺瓦提斯公司 | 农药用嘧啶－4－酮衍生物 |
| HRP970239B1 (en) | 1997-05-09 | 2004-04-30 | Inst Ru Er Bouekovic | Process for the preparation of sulfonyl-pyrimidine derivatives with antitumor activity |
| GT199900185A (es) | 1998-11-06 | 2001-04-18 | Novedosa pirimidin-4-enamina como fungicida. | |
| WO2003018051A1 (en) | 2001-08-27 | 2003-03-06 | Vic Jira | Anti-fungal composition |
| JPWO2005095419A1 (ja) | 2004-04-01 | 2008-02-21 | 武田薬品工業株式会社 | チアゾロピリミジン誘導体 |
| WO2008005303A2 (en) | 2006-06-30 | 2008-01-10 | Janssen Pharmaceutica N.V. | Thiazolopyrimidine modulators of trpv1 |
| EP2114898A2 (en) * | 2007-02-16 | 2009-11-11 | Amgen Inc. | Nitrogen-containing heterocyclyl ketones and their use as c-met inhibitors |
| EP2562175A1 (en) | 2008-01-22 | 2013-02-27 | Dow AgroSciences LLC | 5-fluoro pyrimidine derivatives as fungicides |
| US20100284959A1 (en) * | 2008-01-23 | 2010-11-11 | Gene Arrest Ltd. | Sequence specific double-stranded dna/rna binding compounds and uses thereof |
| EP2647287A1 (en) | 2008-08-01 | 2013-10-09 | Dow AgroSciences LLC | Use of 5-fluorocytosine and its derivatives as fungicides |
| RS54192B1 (sr) * | 2009-01-23 | 2015-12-31 | Euro-Celtique S.A. | Derivati hidroksamske kiseline |
| UA107671C2 (en) * | 2009-08-07 | 2015-02-10 | Dow Agrosciences Llc | N1-substityted-5-fluoro-2-oxopyrimidinone-1(2h)-carboxamide derivatives |
| BR112012002807B1 (pt) | 2009-08-07 | 2018-07-10 | Adama Makhteshim Ltd. | Derivados de 5-flúor-2-oxopirimidina-1(2h)- caboxilato, composição e processo para controle e prevenção de ataque fúngico em uma planta de ataque fúngico em uma planta |
| JP5784603B2 (ja) | 2009-08-07 | 2015-09-24 | ダウ アグロサイエンシィズ エルエルシー | Ｎ１−スルホニル−５−フルオロピリミジノン誘導体 |
| UA106889C2 (uk) * | 2009-08-07 | 2014-10-27 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні n1-ацил-5-фторпіримідинону |
| UA112284C2 (uk) * | 2009-08-07 | 2016-08-25 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні 5-фторпіримідинону |
| MX2012012530A (es) * | 2010-04-26 | 2012-12-17 | Dow Agrosciences Llc | Derivados de n1-sulfonil-5-fluorpirimidinona. |
| EP2672825A4 (en) | 2011-02-11 | 2014-09-10 | Dow Agrosciences Llc | STABLE AGROCHEMICAL OIL DISPERSIONS |
| KR20150103096A (ko) * | 2012-12-28 | 2015-09-09 | 다우 아그로사이언시즈 엘엘씨 | N-(치환된)-5-플루오로-4-이미노-3-메틸-2-옥소-3,4-디히드로피리미딘-1(2h)-카르복실레이트 유도체 |
| MX2015008444A (es) * | 2012-12-28 | 2015-09-23 | Dow Agrosciences Llc | Derivados de n-(sustituido)-5-flouro-4-imino-3-metil-2-oxo-3,4-dih idropirimidin-1 (2h)-carboximida. |
-
2013
- 2013-12-23 EP EP13869394.0A patent/EP2945635A4/en not_active Withdrawn
- 2013-12-23 JP JP2015550733A patent/JP6336480B2/ja active Active
- 2013-12-23 MX MX2015008443A patent/MX2015008443A/es unknown
- 2013-12-23 CA CA2893776A patent/CA2893776A1/en not_active Abandoned
- 2013-12-23 HK HK16102498.5A patent/HK1214518A1/zh unknown
- 2013-12-23 RU RU2018118951A patent/RU2018118951A/ru not_active Application Discontinuation
- 2013-12-23 CN CN201380068093.5A patent/CN104994859B/zh active Active
- 2013-12-23 EP EP19217878.8A patent/EP3689142A1/en active Pending
- 2013-12-23 AU AU2013370470A patent/AU2013370470B2/en not_active Ceased
- 2013-12-23 RU RU2015131110A patent/RU2656101C2/ru not_active IP Right Cessation
- 2013-12-23 US US14/655,568 patent/US9271497B2/en active Active
- 2013-12-23 WO PCT/US2013/077478 patent/WO2014105821A1/en not_active Ceased
- 2013-12-23 KR KR1020157020064A patent/KR20150103095A/ko not_active Withdrawn
- 2013-12-23 UA UAA201507549A patent/UA117123C2/uk unknown
- 2013-12-27 BR BR102013033840A patent/BR102013033840B1/pt active IP Right Grant
-
2015
- 2015-06-10 ZA ZA2015/04195A patent/ZA201504195B/en unknown
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| EP3689142A1 (en) | 2020-08-05 |
| RU2015131110A (ru) | 2017-02-03 |
| CA2893776A1 (en) | 2014-07-03 |
| AU2013370470B2 (en) | 2018-05-10 |
| HK1214518A1 (zh) | 2016-07-29 |
| US9271497B2 (en) | 2016-03-01 |
| RU2018118951A3 (enExample) | 2019-02-26 |
| CL2015001861A1 (es) | 2015-10-02 |
| WO2014105821A1 (en) | 2014-07-03 |
| EP2945635A1 (en) | 2015-11-25 |
| RU2656101C2 (ru) | 2018-05-31 |
| GT201500196A (es) | 2016-03-02 |
| CN104994859A (zh) | 2015-10-21 |
| UA117123C2 (uk) | 2018-06-25 |
| IL239562A0 (en) | 2015-08-31 |
| AU2013370470A1 (en) | 2015-07-02 |
| KR20150103095A (ko) | 2015-09-09 |
| RU2018118951A (ru) | 2018-11-02 |
| BR102013033840A2 (pt) | 2015-10-06 |
| ZA201504195B (en) | 2017-08-30 |
| ECSP15032926A (es) | 2015-11-30 |
| EP2945635A4 (en) | 2016-05-25 |
| HK1216147A1 (zh) | 2016-10-21 |
| IL239562B (en) | 2018-02-28 |
| JP2016509589A (ja) | 2016-03-31 |
| MX2015008443A (es) | 2015-09-23 |
| US20150342188A1 (en) | 2015-12-03 |
| BR102013033840B1 (pt) | 2019-09-10 |
| CN104994859B (zh) | 2018-10-26 |
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