BR102014033010B1 - Processos para preparação de 5-flúor-4-imino-3-(alquil/alquilasubstituída)-1-arilsulfonil) -3,4-di-hidropirimidin-2(1h)ona, seus usos, composição, e processo para controle ou prevenção de ataque fúngico em uma planta - Google Patents
Processos para preparação de 5-flúor-4-imino-3-(alquil/alquilasubstituída)-1-arilsulfonil) -3,4-di-hidropirimidin-2(1h)ona, seus usos, composição, e processo para controle ou prevenção de ataque fúngico em uma planta Download PDFInfo
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- BR102014033010B1 BR102014033010B1 BR102014033010-0A BR102014033010A BR102014033010B1 BR 102014033010 B1 BR102014033010 B1 BR 102014033010B1 BR 102014033010 A BR102014033010 A BR 102014033010A BR 102014033010 B1 BR102014033010 B1 BR 102014033010B1
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- molar ratio
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims description 18
- 230000002265 prevention Effects 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title abstract description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 14
- 239000003513 alkali Substances 0.000 claims abstract description 14
- 239000002168 alkylating agent Substances 0.000 claims abstract description 14
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 26
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 12
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 11
- -1 benzyl halides Chemical class 0.000 claims description 10
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 10
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 7
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 7
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 235000017550 sodium carbonate Nutrition 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims 19
- 230000002538 fungal effect Effects 0.000 claims 3
- 239000002689 soil Substances 0.000 claims 3
- 230000000855 fungicidal effect Effects 0.000 claims 2
- 235000017060 Arachis glabrata Nutrition 0.000 claims 1
- 235000010777 Arachis hypogaea Nutrition 0.000 claims 1
- 244000105624 Arachis hypogaea Species 0.000 claims 1
- 235000018262 Arachis monticola Nutrition 0.000 claims 1
- 235000016068 Berberis vulgaris Nutrition 0.000 claims 1
- 241000335053 Beta vulgaris Species 0.000 claims 1
- 241000530549 Cercospora beticola Species 0.000 claims 1
- XUEGVRUGKRHCCX-UHFFFAOYSA-N Cl.S(=O)(=O)=C1CC=CC=C1 Chemical class Cl.S(=O)(=O)=C1CC=CC=C1 XUEGVRUGKRHCCX-UHFFFAOYSA-N 0.000 claims 1
- 241001281801 Mycosphaerella arachidis Species 0.000 claims 1
- 241000087479 Pseudocercospora fijiensis Species 0.000 claims 1
- 206010037888 Rash pustular Diseases 0.000 claims 1
- 206010039509 Scab Diseases 0.000 claims 1
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 241000228452 Venturia inaequalis Species 0.000 claims 1
- 241001360088 Zymoseptoria tritici Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 244000053095 fungal pathogen Species 0.000 claims 1
- 235000020232 peanut Nutrition 0.000 claims 1
- 208000029561 pustule Diseases 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- FDYDGPMTLJGGMJ-UHFFFAOYSA-N 4-amino-1-(benzenesulfonyl)-5-fluoropyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1S(=O)(=O)C1=CC=CC=C1 FDYDGPMTLJGGMJ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000004293 19F NMR spectroscopy Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- KVUHRPLZWABERU-UHFFFAOYSA-N 5-fluoro-4-imino-3-methyl-1-(4-methylphenyl)sulfonylpyrimidin-2-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(=O)N(C)C(=N)C(F)=C1 KVUHRPLZWABERU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- IGEAUAWXDNMZMF-UHFFFAOYSA-N 4-amino-5-fluoro-1-(4-methylphenyl)sulfonylpyrimidin-2-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(=O)N=C(N)C(F)=C1 IGEAUAWXDNMZMF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
-
- 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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361922582P | 2013-12-31 | 2013-12-31 | |
| US201361922572P | 2013-12-31 | 2013-12-31 | |
| US61/922,572 | 2013-12-31 | ||
| US61/922,582 | 2013-12-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR102014033010A2 BR102014033010A2 (pt) | 2015-10-20 |
| BR102014033010B1 true BR102014033010B1 (pt) | 2021-07-13 |
Family
ID=53480979
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR102014033010-0A BR102014033010B1 (pt) | 2013-12-31 | 2014-12-30 | Processos para preparação de 5-flúor-4-imino-3-(alquil/alquilasubstituída)-1-arilsulfonil) -3,4-di-hidropirimidin-2(1h)ona, seus usos, composição, e processo para controle ou prevenção de ataque fúngico em uma planta |
| BR102014033037-2A BR102014033037B1 (pt) | 2013-12-31 | 2014-12-30 | Processo para preparação de 5-flúor-4-imino-3-(alquil/alquila substituída)-1- arilsulfonil) -3,4-di-hidro-pirimidin-2(1h)-ona |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR102014033037-2A BR102014033037B1 (pt) | 2013-12-31 | 2014-12-30 | Processo para preparação de 5-flúor-4-imino-3-(alquil/alquila substituída)-1- arilsulfonil) -3,4-di-hidro-pirimidin-2(1h)-ona |
Country Status (24)
| Country | Link |
|---|---|
| US (8) | US20150183750A1 (enExample) |
| EP (4) | EP3097096A4 (enExample) |
| JP (3) | JP6804297B2 (enExample) |
| CN (4) | CN111362881A (enExample) |
| AP (1) | AP2016009342A0 (enExample) |
| AU (2) | AU2014373959B2 (enExample) |
| BR (2) | BR102014033010B1 (enExample) |
| CA (2) | CA2935601C (enExample) |
| CL (1) | CL2016001677A1 (enExample) |
| CR (2) | CR20210172A (enExample) |
| DO (1) | DOP2016000163A (enExample) |
| EA (2) | EA036389B1 (enExample) |
| EC (1) | ECSP16064249A (enExample) |
| IL (3) | IL246512B (enExample) |
| MX (2) | MX375727B (enExample) |
| NI (1) | NI201600094A (enExample) |
| NZ (2) | NZ722438A (enExample) |
| PE (1) | PE20161174A1 (enExample) |
| PH (1) | PH12016501284A1 (enExample) |
| SG (2) | SG11201605372QA (enExample) |
| TW (2) | TWI667229B (enExample) |
| UA (2) | UA122200C2 (enExample) |
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| RU2638556C2 (ru) | 2012-12-28 | 2017-12-14 | Адама Мактешим Лтд. | Производные n-(замещенного)-5-фтор-4-имино-3-метил-2-оксо-3,4-дигидропиримидин-1(2н)-карбоксилата |
| RU2015131149A (ru) | 2012-12-28 | 2017-02-03 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | N-(замещенные)-5-фтор-4-имино-3-метил-2-оксо-3,4-дигидропиримидин-1(2н)-карбоксамидные производные |
| MX381341B (es) | 2012-12-31 | 2025-03-12 | Adama Makhteshim Ltd | Derivados de 3-alquil-5-fluoro-4-sustituido-imino-3,4-dihidropirimidin-2(1h)-ona como fungicidas. |
| EA036389B1 (ru) | 2013-12-31 | 2020-11-03 | Адама Мактешим Лтд. | 5-фтор-4-имино-3-(алкил/замещенный алкил)-1-(арилсульфонил)-3,4-дигидропиримидин-2(1h)-он и способы их получения |
| AU2014373853A1 (en) | 2013-12-31 | 2016-08-11 | Adama Makhteshim Ltd. | Synergistic fungicidal mixtures and compositions for fungal control |
| UY36964A (es) | 2015-10-27 | 2017-05-31 | Bayer Cropscience Ag | Combinaciones de principios activos que comprenden un derivado de (tio) carboxamida y un compuesto funguicida |
| JP6922271B2 (ja) * | 2016-03-11 | 2021-08-18 | 住友化学株式会社 | 植物病害防除組成物及び植物病害防除方法 |
| US11632954B2 (en) * | 2017-07-17 | 2023-04-25 | Adama Makhteshim Ltd. | Polymorphs of 5-fluoro-4-imino-3-methyl-1 -tosyl-3,4-dihydropyrimidin-2-one |
| BR112021008755A2 (pt) | 2018-11-05 | 2021-08-10 | Adama Makhteshim Ltd. | misturas e composições contendo 5-fluoro-4-imino-3- metil-1-tosil-3,4-dihidropirimidina-2-ona, e métodos de uso. |
| MX2022000944A (es) | 2019-07-22 | 2022-04-06 | Adama Makhteshim Ltd | Combinaciones, mezclas y composiciones fungicidas y usos de las mismas. |
| 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 |
| WO2021181274A1 (en) * | 2020-03-09 | 2021-09-16 | Adama Makhteshim Ltd. | Process for preparing 5-fluoro-4-imino-3-methyl-1-(toluene-4-sulfonyl)-3,4-dihydro-1h-pyrimidin-2-one |
| MX2022013874A (es) * | 2020-05-04 | 2022-11-30 | Adama Makhteshim Ltd | Mezclas y composiciones que comprenden 5-fluoro-4-imino-3- metil-1-tosil-3,4-dihidropirimidin-2-ona, y metodos de uso de las mismas. |
| IL299711A (en) | 2020-07-08 | 2023-03-01 | Adama Makhteshim Ltd | Fungicidal mixtures |
| US20240172750A1 (en) | 2021-01-27 | 2024-05-30 | Adama Makhteshim Ltd. | 5-Fluoro-4-Imino-3-Methyl-1-Tosyl-3,4-Dihydropyrimidin-2(1H)-One for Controlling Plant Diseases |
| EP4334291A1 (en) | 2021-05-04 | 2024-03-13 | Adama Makhteshim Ltd. | Crystalline forms of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4- dihydropyrimidin-2-one, and mixtures, compositions and methods of use thereof |
| US20240351990A1 (en) | 2021-09-15 | 2024-10-24 | Adama Makhteshim Ltd. | Process for preparing 5-fluoro-4-imino-3-methyl-1-(toluene-4- sulfonyl)-3,4-dihydro-1h-pyrimidin-2-one |
| WO2023166485A1 (en) | 2022-03-03 | 2023-09-07 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
| EP4609713A3 (en) | 2022-05-26 | 2025-10-29 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
| AR130107A1 (es) | 2022-08-03 | 2024-11-06 | Adama Makhteshim Ltd | 5-fluoro-4-imino-3-metil-1-tosil-3,4-dihidropirimidin-2(1h)-ona para hongos resistentes a fungicidas |
| CN120882310A (zh) | 2023-03-09 | 2025-10-31 | 安道麦马克西姆有限公司 | 杀真菌组合、混合物及组合物以及其用途 |
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| WO2025046581A1 (en) | 2023-08-31 | 2025-03-06 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereo |
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