PL422979A1 - N-benzyltriticonazole salts, method for obtaining them and application as fungicides - Google Patents
N-benzyltriticonazole salts, method for obtaining them and application as fungicidesInfo
- Publication number
- PL422979A1 PL422979A1 PL422979A PL42297917A PL422979A1 PL 422979 A1 PL422979 A1 PL 422979A1 PL 422979 A PL422979 A PL 422979A PL 42297917 A PL42297917 A PL 42297917A PL 422979 A1 PL422979 A1 PL 422979A1
- Authority
- PL
- Poland
- Prior art keywords
- application
- benzyltrithiconazole
- acetonitrile
- group
- inorganic
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 abstract 2
- 239000005859 Triticonazole Substances 0.000 abstract 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 abstract 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 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 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 238000005349 anion exchange Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 150000003893 lactate salts Chemical class 0.000 abstract 1
- 150000002823 nitrates Chemical class 0.000 abstract 1
- 150000002891 organic anions Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 150000003873 salicylate salts Chemical class 0.000 abstract 1
- 229960004889 salicylic acid Drugs 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- -1 tetrafluoroborates Chemical class 0.000 abstract 1
- 150000003567 thiocyanates Chemical class 0.000 abstract 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Przedmiotem zgłoszenia są sole N-benzylotritikonazolu o wzorze ogólnym 1, w którym A oznacza anion organiczny z grupy: mleczanów, lub salicylanów, lub octanów, lub nieorganiczny z grupy: tetrafluoroboranów, lub tiocyjanianów, lub azotanów(V). Zgłoszenie obejmuje też sposób ich otrzymywania, który polega na tym, że tritikonazol poddaje się reakcji czwartorzędowania z bromkiem benzylu w stosunku molowym tritikonazolu do bromku benzylu od 1:1 do 1:1,1, w rozpuszczalniku organicznym z grupy: acetonitryl, lub metanol, lub izopropanol, lub etanol, korzystnie acetonitryl, w temperaturze od 20 do 80°C, korzystnie 60°C, po czym otrzymany bromek N-benzylotritikonazolu o wzorze ogólnym 2 poddaje się reakcji wymiany anionu z solą sodową albo potasową kwasu mlekowego, albo salicylowego, albo octowego, albo tetrafluoroborowego, albo tiocyjanowego, albo azotowego(V) w rozpuszczalniku: acetonie, albo acetonitrylu, albo metanolu, albo izopropanolu, albo etanolu, w stosunku molowym czwartorzędowej soli amoniowej do soli nieorganicznej od 1:1 do 1:1,05, korzystnie 1:1, w temperaturze od 20 do 80°C, korzystnie 50°C, w czasie co najmniej 30 minut, następnie odsącza się wytrącony osad nieorganiczny, dalej odparowuje się rozpuszczalnik, a produkt suszy pod obniżonym ciśnieniem. Przedmiotem zgłoszenia jest też zastosowanie soli N-benzylotritikonazolu jako fungicydów.The subject of the application are the salts of N-benzyltrithiconazole of general formula 1, in which A is an organic anion from the group: lactates, or salicylates, or acetates, or inorganic from the group: tetrafluoroborates, or thiocyanates, or nitrates (V). The application also includes a method for their preparation, which consists in the fact that triticonazole is subjected to a quaternization reaction with benzyl bromide in a molar ratio of triticonazole to benzyl bromide from 1: 1 to 1: 1.1, in an organic solvent from the group: acetonitrile, or methanol, or isopropanol or ethanol, preferably acetonitrile, at a temperature of 20 to 80 ° C, preferably 60 ° C, after which the obtained N-benzyltrithiconazole bromide of general formula 2 is subjected to anion exchange reaction with a sodium or potassium salt of lactic or salicylic acid, or acetic or tetrafluoroboric or thiocyanate or nitrogen (V) solvent in acetone or acetonitrile or methanol or isopropanol or ethanol in a molar ratio of quaternary ammonium salt to inorganic salt from 1: 1 to 1: 1.05 , preferably 1: 1, at a temperature of 20 to 80 ° C, preferably 50 ° C, for at least 30 minutes, then the inorganic precipitate is filtered off, the further evaporation is carried out solvent and the product is dried under reduced pressure. The subject of the application is also the use of N-benzyltrithiconazole as fungicides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422979A PL233297B1 (en) | 2017-09-26 | 2017-09-26 | N-benzyltriticonazole salts, method for obtaining them and application as fungicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422979A PL233297B1 (en) | 2017-09-26 | 2017-09-26 | N-benzyltriticonazole salts, method for obtaining them and application as fungicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL422979A1 true PL422979A1 (en) | 2019-04-08 |
| PL233297B1 PL233297B1 (en) | 2019-09-30 |
Family
ID=65992030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL422979A PL233297B1 (en) | 2017-09-26 | 2017-09-26 | N-benzyltriticonazole salts, method for obtaining them and application as fungicides |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL233297B1 (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007107556A1 (en) * | 2006-03-21 | 2007-09-27 | Basf Se | Enantiomerically pure triticonazole |
| WO2011070771A1 (en) * | 2009-12-08 | 2011-06-16 | Kureha Corporation | Azole derivatives, methods for producing the same, intermediate thereof, agro-horticultural agents |
| PL400714A1 (en) * | 2012-09-10 | 2014-03-17 | Instytut Ochrony Roslin | Propiconazole salts and processes for their preparation |
| PL400713A1 (en) * | 2012-09-10 | 2014-03-17 | Instytut Ochrony Roslin | Tebuconazole salts and processes for their preparation |
| EP2716634A1 (en) * | 2011-05-31 | 2014-04-09 | Kureha Corporation | Triazole compound and use thereof |
-
2017
- 2017-09-26 PL PL422979A patent/PL233297B1/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007107556A1 (en) * | 2006-03-21 | 2007-09-27 | Basf Se | Enantiomerically pure triticonazole |
| WO2011070771A1 (en) * | 2009-12-08 | 2011-06-16 | Kureha Corporation | Azole derivatives, methods for producing the same, intermediate thereof, agro-horticultural agents |
| EP2716634A1 (en) * | 2011-05-31 | 2014-04-09 | Kureha Corporation | Triazole compound and use thereof |
| PL400714A1 (en) * | 2012-09-10 | 2014-03-17 | Instytut Ochrony Roslin | Propiconazole salts and processes for their preparation |
| PL400713A1 (en) * | 2012-09-10 | 2014-03-17 | Instytut Ochrony Roslin | Tebuconazole salts and processes for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| PL233297B1 (en) | 2019-09-30 |
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