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 (enExample) | 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 (enExample) |
| EP (1) | EP3655396A1 (enExample) |
| JP (3) | JP2020527563A (enExample) |
| CN (2) | CN118515619A (enExample) |
| AR (1) | AR112276A1 (enExample) |
| AU (1) | AU2018320492C1 (enExample) |
| CA (1) | CA3069619A1 (enExample) |
| IL (5) | IL309708B1 (enExample) |
| MA (1) | MA49639A (enExample) |
| WO (1) | WO2019038583A1 (enExample) |
| ZA (1) | ZA202000411B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA202191250A1 (ru) | 2018-11-05 | 2021-08-20 | Адама Мактешим Лтд. | Смеси и композиции, включающие 5-фтор-4-имино-3-метил-1-тозил-3,4-дигидропиримидин-2-он, и способы их применения |
| JP2022541318A (ja) * | 2019-07-22 | 2022-09-22 | アダマ・マクテシム・リミテッド | 殺菌組合せ物、混合物および組成物、ならびにそれらの使用 |
| US12466796B2 (en) * | 2019-09-23 | 2025-11-11 | Adama Makhteshim Ltd. | Process for preparing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine-(1H)-one and derivatives of the compound |
| AU2021267206A1 (en) * | 2020-05-04 | 2022-12-08 | 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 |
| CA3206570A1 (en) | 2021-01-27 | 2022-08-04 | Alexandra ROSENMUND | 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1 h)-one for controlling plant diseases |
| CA3216622A1 (en) | 2021-05-04 | 2022-11-10 | Stefano Luca Giaffreda | Crystalline forms of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4- dihydropyrimidin-2-one, and mixtures, compositions and methods of use thereof |
| AU2023227455A1 (en) | 2022-03-03 | 2024-09-19 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
| CA3257550A1 (en) | 2022-05-26 | 2023-11-30 | Adama Makhteshim Ltd. | FUNGICIDAL COMBINATIONS, MIXTURES AND COMPOSITIONS AND THEIR USES |
| EP4565066A1 (en) | 2022-08-03 | 2025-06-11 | 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 |
| WO2024189563A1 (en) | 2023-03-14 | 2024-09-19 | 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 |
| WO2025114931A1 (en) | 2023-11-28 | 2025-06-05 | Adama Makhteshim Ltd. | Fungicidal combinations, mixtures and compositions and uses thereof |
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| US3868373A (en) | 1970-01-27 | 1975-02-25 | Hoffmann La Roche | 4-Amino-5-fluoro-2-tri(lower alkyl) silyloxypyrimidines |
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| US4845081A (en) | 1984-10-18 | 1989-07-04 | University Of Florida | Aminomethyl derivatives of biologically active substances, and enhanced delivery thereof across topical membranes |
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| UA106246C2 (ru) | 2009-10-07 | 2014-08-11 | ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі | Синергическая фунгицидная композиция, которая содержит 5-фторцитозин для борьбы с грибковыми болезнями зерновых культур |
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