JP6258969B2 - Ｎ−（置換）−５−フルオロ−４−イミノ−３−メチル−２−オキソ−３，４−ジヒドロピリミジン−１（２ｈ）−カルボキサミド誘導体 - Google Patents
Ｎ−（置換）−５−フルオロ−４−イミノ−３−メチル−２−オキソ−３，４−ジヒドロピリミジン−１（２ｈ）−カルボキサミド誘導体 Download PDFInfo
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- JP6258969B2 JP6258969B2 JP2015550741A JP2015550741A JP6258969B2 JP 6258969 B2 JP6258969 B2 JP 6258969B2 JP 2015550741 A JP2015550741 A JP 2015550741A JP 2015550741 A JP2015550741 A JP 2015550741A JP 6258969 B2 JP6258969 B2 JP 6258969B2
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- Prior art keywords
- compound
- phenyl
- salt
- benzyl
- hydrate
- Prior art date
- 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.)
- Expired - Fee Related
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- -1 N- (substituted) -5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1 (2H) -carboxamide Chemical class 0.000 title claims description 184
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 109
- 239000000203 mixture Substances 0.000 claims description 49
- 230000000855 fungicidal effect Effects 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 8
- 241001360088 Zymoseptoria tritici Species 0.000 claims description 7
- 229910052799 carbon Inorganic materials 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
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 208000031888 Mycoses Diseases 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000012876 carrier material Substances 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 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
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 40
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- 239000000417 fungicide Substances 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 201000010099 disease Diseases 0.000 description 10
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- 238000002360 preparation method Methods 0.000 description 10
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 8
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- 239000004094 surface-active agent Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 6
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- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 150000001412 amines Chemical class 0.000 description 5
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- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000010949 copper Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 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
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- 230000000361 pesticidal effect Effects 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
- 241000894007 species Species 0.000 description 4
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- 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
- 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
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 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
- 239000012141 concentrate 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
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- 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
- 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
- KYALOMRPLRTWCC-UHFFFAOYSA-N n-(4-chlorophenyl)-5-fluoro-4-imino-3-methyl-2-oxopyrimidine-1-carbothioamide Chemical compound O=C1N(C)C(=N)C(F)=CN1C(=S)NC1=CC=C(Cl)C=C1 KYALOMRPLRTWCC-UHFFFAOYSA-N 0.000 description 3
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- 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
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- 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
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- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 2
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- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 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
-
- 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
-
- 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
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261746837P | 2012-12-28 | 2012-12-28 | |
| US61/746,837 | 2012-12-28 | ||
| PCT/US2013/077533 WO2014105841A1 (en) | 2012-12-28 | 2013-12-23 | N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1 (2h)-carboxamides derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016505605A JP2016505605A (ja) | 2016-02-25 |
| JP2016505605A5 JP2016505605A5 (enExample) | 2017-02-09 |
| JP6258969B2 true JP6258969B2 (ja) | 2018-01-10 |
Family
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Family Applications (1)
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|---|---|---|---|
| JP2015550741A Expired - Fee Related JP6258969B2 (ja) | 2012-12-28 | 2013-12-23 | Ｎ−（置換）−５−フルオロ−４−イミノ−３−メチル−２−オキソ−３，４−ジヒドロピリミジン−１（２ｈ）−カルボキサミド誘導体 |
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| EP (1) | EP2945634A4 (enExample) |
| JP (1) | JP6258969B2 (enExample) |
| KR (1) | KR20150100869A (enExample) |
| CN (1) | CN104884062B (enExample) |
| AU (1) | AU2013370490B2 (enExample) |
| BR (1) | BR102013033716B1 (enExample) |
| CA (1) | CA2894510A1 (enExample) |
| CL (1) | CL2015001863A1 (enExample) |
| EC (1) | ECSP15032846A (enExample) |
| GT (1) | GT201500195A (enExample) |
| HK (1) | HK1215376A1 (enExample) |
| IL (1) | IL239563B (enExample) |
| MX (1) | MX2015008444A (enExample) |
| RU (1) | RU2015131149A (enExample) |
| UA (1) | UA117743C2 (enExample) |
| WO (1) | WO2014105841A1 (enExample) |
| ZA (1) | ZA201504197B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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. |
| 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 |
| EP2945635A4 (en) * | 2012-12-28 | 2016-05-25 | Dow Agrosciences Llc | 1- (SUBSTITUTED BENZOYL) -5-FLUORO-4-IMINO-3-METHYL-3,4-DIHYDROPYRIMIDIN-2 (1H) -ONE DERIVATIVES |
| 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 |
| 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 |
| EA030056B1 (ru) | 2013-12-31 | 2018-06-29 | Адама Мактешим Лтд. | Синергетические фунгицидные смеси и синергетические фунгицидные композиции для борьбы с грибами |
| MX2017008418A (es) | 2014-12-30 | 2017-09-28 | Dow Agrosciences Llc | Picolinamidas con actividad fungicida. |
| WO2016109302A1 (en) | 2014-12-30 | 2016-07-07 | Dow Agrosciences Llc | Picolinamide compounds with fungicidal activity |
| EP3240413B1 (en) | 2014-12-30 | 2020-05-13 | Dow Agrosciences LLC | Picolinamide compounds with fungicidal activity |
| 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 |
| EP3614845B1 (en) * | 2017-04-27 | 2023-11-01 | UPL Ltd | Fungicidal combinations |
| 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 |
| 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 |
| 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 |
| 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 |
| MX2021003530A (es) * | 2018-09-27 | 2021-05-27 | Fmc Corp | Herbicidas de piridazinona e intermediarios de piridazinona usados para preparar un herbicida. |
| 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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| Publication number | Publication date |
|---|---|
| US20150353506A1 (en) | 2015-12-10 |
| US20160198711A1 (en) | 2016-07-14 |
| BR102013033716A2 (pt) | 2015-11-10 |
| JP2016505605A (ja) | 2016-02-25 |
| ECSP15032846A (es) | 2016-01-29 |
| KR20150100869A (ko) | 2015-09-02 |
| US9840475B2 (en) | 2017-12-12 |
| IL239563A0 (en) | 2015-08-31 |
| UA117743C2 (uk) | 2018-09-25 |
| GT201500195A (es) | 2016-02-14 |
| CL2015001863A1 (es) | 2015-10-02 |
| MX2015008444A (es) | 2015-09-23 |
| EP2945634A1 (en) | 2015-11-25 |
| CN104884062B (zh) | 2018-11-06 |
| HK1215376A1 (zh) | 2016-08-26 |
| CN104884062A (zh) | 2015-09-02 |
| AU2013370490B2 (en) | 2018-05-10 |
| US9321734B2 (en) | 2016-04-26 |
| RU2015131149A (ru) | 2017-02-03 |
| IL239563B (en) | 2018-02-28 |
| AU2013370490A1 (en) | 2015-07-02 |
| WO2014105841A1 (en) | 2014-07-03 |
| EP2945634A4 (en) | 2016-05-25 |
| ZA201504197B (en) | 2017-04-26 |
| BR102013033716B1 (pt) | 2019-05-14 |
| CA2894510A1 (en) | 2014-07-03 |
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