JP2020527563A5 - - Google Patents
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- JP2020527563A5 JP2020527563A5 JP2020502159A JP2020502159A JP2020527563A5 JP 2020527563 A5 JP2020527563 A5 JP 2020527563A5 JP 2020502159 A JP2020502159 A JP 2020502159A JP 2020502159 A JP2020502159 A JP 2020502159A JP 2020527563 A5 JP2020527563 A5 JP 2020527563A5
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- 239000000203 mixture Substances 0.000 claims description 98
- 239000013078 crystal Substances 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 48
- 239000007787 solid Substances 0.000 claims description 33
- 238000001914 filtration Methods 0.000 claims description 28
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 28
- 230000000855 fungicidal effect Effects 0.000 claims description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 241000233866 Fungi Species 0.000 claims description 23
- 238000002425 crystallisation Methods 0.000 claims description 22
- 230000008025 crystallization Effects 0.000 claims description 22
- 239000000417 fungicide Substances 0.000 claims description 22
- 239000003960 organic solvent Substances 0.000 claims description 21
- 230000002538 fungal effect Effects 0.000 claims description 18
- 206010061217 Infestation Diseases 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 238000005507 spraying Methods 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 10
- 238000000354 decomposition reaction Methods 0.000 claims description 10
- 238000000003 thermogravimetry coupled to Fourier transform infrared spectroscopy Methods 0.000 claims description 10
- 238000001757 thermogravimetry curve Methods 0.000 claims description 10
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical group CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 238000007614 solvation Methods 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 229930182558 Sterol Natural products 0.000 claims description 4
- 102000019259 Succinate Dehydrogenase Human genes 0.000 claims description 4
- 108010012901 Succinate Dehydrogenase Proteins 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000003432 sterols Chemical class 0.000 claims description 4
- 235000003702 sterols Nutrition 0.000 claims description 4
- 229930182692 Strobilurin Natural products 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 239000008247 solid mixture Substances 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 238000004659 sterilization and disinfection Methods 0.000 claims description 2
- 230000002195 synergetic effect Effects 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 230000003071 parasitic effect Effects 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical group N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 description 2
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 2
- 239000005745 Captan Substances 0.000 description 2
- 239000005757 Cyproconazole Substances 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- 239000005783 Fluopyram Substances 0.000 description 2
- 239000005789 Folpet Substances 0.000 description 2
- 239000005799 Isopyrazam Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000005822 Propiconazole Substances 0.000 description 2
- 239000005825 Prothioconazole Substances 0.000 description 2
- 229940117949 captan Drugs 0.000 description 2
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 description 2
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 2
- -1 microbutanyl Substances 0.000 description 2
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 1
- GOFJDXZZHFNFLV-UHFFFAOYSA-N 5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C GOFJDXZZHFNFLV-UHFFFAOYSA-N 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- HOZRMSNCAJGJAT-UHFFFAOYSA-N CCc(cc1)ccc1S(N(CC(C)(C(N1C)=N)F)C1=O)(=O)=O Chemical compound CCc(cc1)ccc1S(N(CC(C)(C(N1C)=N)F)C1=O)(=O)=O HOZRMSNCAJGJAT-UHFFFAOYSA-N 0.000 description 1
- KVUHRPLZWABERU-UHFFFAOYSA-N Cc(cc1)ccc1S(N(C=C(C(N1C)=N)F)C1=O)(=O)=O Chemical compound Cc(cc1)ccc1S(N(C=C(C(N1C)=N)F)C1=O)(=O)=O KVUHRPLZWABERU-UHFFFAOYSA-N 0.000 description 1
- 239000005775 Fenbuconazole Substances 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 239000005868 Metconazole Substances 0.000 description 1
- 239000005815 Penflufen Substances 0.000 description 1
- 239000005818 Picoxystrobin Substances 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005840 Tetraconazole Substances 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-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
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023118871A JP2023145572A (ja) | 2017-07-17 | 2023-07-21 | ５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２－オンの多形体 |
| JP2025124685A JP2025163080A (ja) | 2017-07-17 | 2025-07-25 | ５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２－オンの多形体 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762533509P | 2017-07-17 | 2017-07-17 | |
| US62/533,509 | 2017-07-17 | ||
| PCT/IB2018/000875 WO2019038583A1 (en) | 2017-07-17 | 2018-07-16 | 5-FLUORO-4-IMINO-3-METHYL-1-TOSYL-3,4-DIHYDROPYRIMIDIN-2-ONE POLYMORPHS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023118871A Division JP2023145572A (ja) | 2017-07-17 | 2023-07-21 | ５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２－オンの多形体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020527563A JP2020527563A (ja) | 2020-09-10 |
| JP2020527563A5 true JP2020527563A5 (https=) | 2021-08-26 |
Family
ID=63517924
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020502159A Pending JP2020527563A (ja) | 2017-07-17 | 2018-07-16 | ５−フルオロ−４−イミノ−３−メチル−１−トシル−３，４−ジヒドロピリミジン−２−オンの多形体 |
| JP2023118871A Pending JP2023145572A (ja) | 2017-07-17 | 2023-07-21 | ５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２－オンの多形体 |
| JP2025124685A Pending JP2025163080A (ja) | 2017-07-17 | 2025-07-25 | ５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２－オンの多形体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023118871A Pending JP2023145572A (ja) | 2017-07-17 | 2023-07-21 | ５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２－オンの多形体 |
| JP2025124685A Pending JP2025163080A (ja) | 2017-07-17 | 2025-07-25 | ５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２－オンの多形体 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US11632954B2 (https=) |
| EP (1) | EP3655396A1 (https=) |
| JP (3) | JP2020527563A (https=) |
| CN (2) | CN118515619A (https=) |
| AR (1) | AR112276A1 (https=) |
| AU (1) | AU2018320492C1 (https=) |
| CA (1) | CA3069619A1 (https=) |
| IL (5) | IL309708B2 (https=) |
| MA (1) | MA49639A (https=) |
| WO (1) | WO2019038583A1 (https=) |
| ZA (1) | ZA202000411B (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3876717A1 (en) | 2018-11-05 | 2021-09-15 | Adama Makhteshim Ltd. | Mixtures and compositions comprising 5-fluoro-4-imino-3- methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and methods of use thereof |
| IL321760A (en) * | 2019-07-22 | 2025-08-01 | Adama Makhteshim Ltd | Fungicidal combinations, mixtures and compositions and uses thereof |
| PY2057637A (es) * | 2019-09-23 | 2021-10-05 | Adama Makhteshim Ltd | Proceso para preparar 5-(fluoro-4-imino-3-metil)-1-tosil-3,4-dihidropirimidin-(1h)-ona y derivados del compuesto |
| EP4146632A1 (en) * | 2020-05-04 | 2023-03-15 | Adama Makhteshim Ltd. | Mixtures and compositions comprising 5-fluoro-4-imino-3- methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and methods of use thereof |
| BR112023014997A2 (pt) | 2021-01-27 | 2023-10-03 | Adama Makhteshim Ltd | 5-fluoro-4-imino-3-metil-1-tosil-3,4-di-hidropirimidin-2(1h)-ona para controle de doenças de plantas |
| US20240237649A1 (en) | 2021-05-04 | 2024-07-18 | 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 |
| UY40172A (es) | 2022-03-03 | 2023-10-13 | Adama Makhteshim Ltd | Combinaciones, mezclas y composiciones fungicidas y usos de las mismas |
| EP4609713A3 (en) | 2022-05-26 | 2025-10-29 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
| AU2023318916A1 (en) | 2022-08-03 | 2025-02-20 | Adama Makhteshim Ltd. | 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1h)-one for fungicide-resistant fungus |
| AU2024233301A1 (en) | 2023-03-09 | 2025-09-18 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
| AU2024236967A1 (en) | 2023-03-14 | 2025-09-25 | Adama Makhteshim Ltd. | Liquid compositions containing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine-(1h)-one and derivatives thereof and a uv absorber |
| AR132381A1 (es) | 2023-04-11 | 2025-06-18 | Adama Makhteshim Ltd | Compuestos y procesos relativos a flumetilsulforim |
| WO2025046581A1 (en) | 2023-08-31 | 2025-03-06 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereo |
| PY24105707A (es) | 2023-11-28 | 2025-06-25 | Adama Makhteshim Ltd | Combinaciones, mezclas y composiciones fungicidas y usos de las mismas |
| WO2026038217A1 (en) | 2024-08-15 | 2026-02-19 | Adama Makhteshim Ltd. | Mixtures and compositions comprising flumetylsulforim and methods of use thereof |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US3635977A (en) | 1969-11-03 | 1972-01-18 | American Cyanamid Co | Certain 6-trifluoromethylcytosines and thiocytosines their synthesis and their use in the synthesis of uracisls and thiouracil |
| US3868373A (en) | 1970-01-27 | 1975-02-25 | Hoffmann La Roche | 4-Amino-5-fluoro-2-tri(lower alkyl) silyloxypyrimidines |
| US4009272A (en) | 1971-10-23 | 1977-02-22 | Bayer Aktiengesellschaft | Penicillins |
| US4845081A (en) | 1984-10-18 | 1989-07-04 | University Of Florida | Aminomethyl derivatives of biologically active substances, and enhanced delivery thereof across topical membranes |
| DE3821711A1 (de) | 1988-06-28 | 1990-02-08 | Bayer Ag | Thiazolopyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| 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 |
| BR9609613A (pt) | 1995-07-05 | 1999-05-25 | Du Pont | Composto composição fungicida e método de controle de doenças de plantas |
| GT199900185A (es) | 1998-11-06 | 2001-04-18 | Novedosa pirimidin-4-enamina como fungicida. | |
| US7914799B2 (en) | 2001-08-27 | 2011-03-29 | Immunitor USA, Inc. | Anti-fungal composition |
| US20080269238A1 (en) | 2004-04-01 | 2008-10-30 | Takeda Pharmaceutical Company Limited | Thiazolopyrimidine Derivative |
| EP1798225A1 (en) | 2004-09-16 | 2007-06-20 | Gifu University | Nucleoside analogues or salts thereof |
| AU2006274070C1 (en) | 2005-07-27 | 2012-03-29 | Basf Se | Fungicidal mixtures based on azolopyrimidinylamines |
| TWI402034B (zh) | 2005-07-28 | 2013-07-21 | Dow Agrosciences Llc | 具有被層狀液晶覆膜包覆之油球之水包油乳化劑之農用組成物 |
| IL172137A0 (en) * | 2005-11-23 | 2006-04-10 | Maktheshim Chemical Works Ltd | Process for prep aring pyridinamines |
| WO2008005303A2 (en) | 2006-06-30 | 2008-01-10 | Janssen Pharmaceutica N.V. | Thiazolopyrimidine modulators of trpv1 |
| US20100029483A1 (en) | 2006-10-16 | 2010-02-04 | Rhodia Inc. | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
| US8093245B2 (en) | 2006-12-14 | 2012-01-10 | Lexicon Pharmaceuticals, Inc. | 4-amino-1H-pyrimidin-2-one based compounds, compositions comprising them and methods of their use |
| IL181125A0 (en) * | 2007-02-01 | 2007-07-04 | Maktheshim Chemical Works Ltd | Polymorphs of 3-(e)-2-{2-[6-(2- |
| AU2008219166B2 (en) | 2007-02-16 | 2013-05-16 | Amgen Inc. | Nitrogen-containing heterocyclyl ketones and their use as c-Met inhibitors |
| PT2562166E (pt) | 2008-01-22 | 2015-10-28 | Dow Agrosciences Llc | Derivados de 5-fluoro-pirimidina como fungicidas |
| US20100284959A1 (en) | 2008-01-23 | 2010-11-11 | Gene Arrest Ltd. | Sequence specific double-stranded dna/rna binding compounds and uses thereof |
| CN102215691B (zh) | 2008-08-01 | 2015-02-04 | 陶氏益农公司 | 5-氟胞嘧啶作为杀真菌剂的用途 |
| JP2012530100A (ja) | 2009-06-18 | 2012-11-29 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺菌剤混合物 |
| 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 |
| ES2471371T3 (es) | 2009-08-07 | 2014-06-26 | Dow Agrosciences Llc | Derivados de N1-sulfonil-5-fluoropirimidinona |
| UA106889C2 (uk) | 2009-08-07 | 2014-10-27 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні n1-ацил-5-фторпіримідинону |
| UA107671C2 (en) | 2009-08-07 | 2015-02-10 | Dow Agrosciences Llc | N1-substityted-5-fluoro-2-oxopyrimidinone-1(2h)-carboxamide derivatives |
| UA112284C2 (uk) | 2009-08-07 | 2016-08-25 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Похідні 5-фторпіримідинону |
| NZ599124A (en) | 2009-10-07 | 2014-03-28 | Dow Agrosciences Llc | Synergistic fungicidal composition containing 5-fluorocytosine for fungal control in cereals |
| PH12012502138B1 (en) | 2010-04-26 | 2019-09-25 | Adama Makhteshim Ltd | N3-substituted-n1-sulfonyl-5-fluoropyrimidinone derivatives |
| US20120208700A1 (en) | 2011-02-11 | 2012-08-16 | Dow Agrosciences Llc | Stable agrochemical oil dispersions |
| WO2013025795A1 (en) | 2011-08-17 | 2013-02-21 | Dow Agrosciences Llc | 5-fluoro-4-imino-3-(substituted)-3,4-dihydropyrimidin-2-(1h)-one derivatives |
| CA2894510A1 (en) | 2012-12-28 | 2014-07-03 | Dow Agrosciences Llc | N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2h)-carboxamide derivatives |
| MX2015008443A (es) | 2012-12-28 | 2015-09-23 | Dow Agrosciences Llc | Derivados de 1-(benzoilo-sustituido) -5-fluoro-4-imino-3-metil-3, 4-dihidropirimidin-2 (1h)-ona. |
| AU2013370494B2 (en) * | 2012-12-31 | 2017-08-17 | Adama Makhteshim Ltd. | 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides |
| TWI652012B (zh) * | 2013-05-20 | 2019-03-01 | 杜邦股份有限公司 | 殺真菌吡唑的固態形式 |
| CA2935594C (en) * | 2013-12-31 | 2022-05-03 | Nakyen Choy | 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation |
| NZ722419A (en) | 2013-12-31 | 2018-01-26 | Adama Makhteshim Ltd | Synergistic fungicidal mixtures and compositions for fungal control |
| MA41272A (fr) | 2014-12-23 | 2017-10-31 | Adama Makhteshim Ltd | 5-fluoro-4-imino-3-(alkyle/alkyle substitué)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one en tant que traitement des semences |
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2018
- 2018-07-16 EP EP18765708.5A patent/EP3655396A1/en active Pending
- 2018-07-16 CA CA3069619A patent/CA3069619A1/en active Pending
- 2018-07-16 MA MA049639A patent/MA49639A/fr unknown
- 2018-07-16 US US16/632,068 patent/US11632954B2/en active Active
- 2018-07-16 AU AU2018320492A patent/AU2018320492C1/en active Active
- 2018-07-16 JP JP2020502159A patent/JP2020527563A/ja active Pending
- 2018-07-16 IL IL309708A patent/IL309708B2/en unknown
- 2018-07-16 IL IL271950A patent/IL271950B2/en unknown
- 2018-07-16 CN CN202410543394.9A patent/CN118515619A/zh active Pending
- 2018-07-16 WO PCT/IB2018/000875 patent/WO2019038583A1/en not_active Ceased
- 2018-07-16 CN CN201880059865.1A patent/CN111094252B/zh active Active
- 2018-07-17 AR ARP180101983 patent/AR112276A1/es unknown
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2020
- 2020-01-21 ZA ZA2020/00411A patent/ZA202000411B/en unknown
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2023
- 2023-07-21 JP JP2023118871A patent/JP2023145572A/ja active Pending
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2025
- 2025-07-25 JP JP2025124685A patent/JP2025163080A/ja active Pending
- 2025-09-10 IL IL323268A patent/IL323268A/en unknown
- 2025-09-10 IL IL323266A patent/IL323266A/en unknown
- 2025-09-10 IL IL323267A patent/IL323267A/en unknown
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