CS263363B1 - 2,6-dimethylphenylcarbamoylmethylpyridiniumchloride and process for preparing thereof - Google Patents
2,6-dimethylphenylcarbamoylmethylpyridiniumchloride and process for preparing thereof Download PDFInfo
- Publication number
- CS263363B1 CS263363B1 CS871433A CS143387A CS263363B1 CS 263363 B1 CS263363 B1 CS 263363B1 CS 871433 A CS871433 A CS 871433A CS 143387 A CS143387 A CS 143387A CS 263363 B1 CS263363 B1 CS 263363B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- chloroacetyl
- dimethylaniline
- dimethylphenylcarbamoylmethylpyridiniumchloride
- hours
- Prior art date
Links
- OJCYCQZJQFAKEP-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-pyridin-1-ium-1-ylacetamide;chloride Chemical compound [Cl-].CC1=CC=CC(C)=C1NC(=O)C[N+]1=CC=CC=C1 OJCYCQZJQFAKEP-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 6
- FPQQSNUTBWFFLB-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CCl FPQQSNUTBWFFLB-UHFFFAOYSA-N 0.000 claims abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 241000196324 Embryophyta Species 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
263363 2
Predmetom vynálezu je herbicídne účinný 2,6-dimetylfenylkarbamoylmetylpyridíniumchlorida jeho spdsob přípravy. Z literatúry je známe, že deriváty N-chlóracetyl-2,6-dialkylanilínovsú herbicidy, fungicidy a regulátory rastu. (Chupp J. P., CH 643 530, Moser H., Vogel CH., EP 115 470, Vogel CH., US 4 283 221, Ranného Co,, Jpn. Kokai 5 984 852).
Teraz sme zistili, že látka obecného vzorca I
(18 sa připravuje spdsobom, ktorý spočívá v reakcii N-chlóracetyl-2,6-dimetylanilínu s pyridínomv prostředí cyklohexánu pri teplete miestnosti po dobu troch hodin.
Nasledujúci příklad bližšie vysvětluje, ale nijako neobmedzuje přípravu zlúčeniny podlávynálezu. Příklad 1 2,6-dimetylfenylkarbamoylmetylpyridíniumchlorid V trojhrdlovej banke opatrenej mieSadlom, spatným chladičom a prikvapkávacim lievikom, sa mieša 25 cm3 cyklohexánu s 0,1 mol (19,8 g) N-chlóracetyl-2,6-dimetylanilínom. Do roztoku3 sa prikvapká 0,1 mol (8 cm ) suchého pyridinu. Po dvojhodinovom miešani pri teplote miestnostiz reakčného prostredia sa vylúči olej, ktorý rýchlo tuhne. Surový produkt krystalizuje z éteru, t.t. 98 až 100 °C. Výtažok 85 %. Sumárny vzorec: C15H17N2OC1 M: 276,74 Analýza: Vyp. % C: 65,70 Zist.: % C: 65,35 % H: 5,19 % H: 4,97 » N: 10,12 « N: 9,95 « Cl: 12,81 % Cl: 12,56
Herbicídny účinok zlúčeniny podlá vynálezu
Zlúčenina podlá vynálezu Dávka úč. 1. na ha Echinochloa erus-galli 1 5,0 5 3,5 5 2,5 5 1.75 4 1,25 4 0,875 3,5 0,625 2,5 Hetachlór 5,0 5 (Standard) 3,5 5 2,5 5 1,75 5 1,25 4,5 0,875 4 0,625 4
Claims (3)
- 263363 pokračovánle tabulky Zlúčeninapodlá vynálezu Dávka úč, 1. na ha Echinochloa crus-galli Chlórtoluron 5,0 3 (Standard) 3,5 2,5 2,5 2,5 1,75 2,5 1,25 0 0,875 0 0,625 0 Bonitačný stupeň: 2 - rastliny zretelne atakované, 3 - rastliny značné atakované, 4 - rastliny ťažko atakované, 5 - rastliny uhynuté. Pracovný postup: Do nádob naplněných neošetrenou pieskovitohlinitou půdou sa vysialisemená testovacích rastlín. Po urovnaní a zavlaženi povrchu půdy následovala aplikácia od-stupňovaných vodných koncentrácií testovaných látok. Objem aplikačného roztoku zodpovedalobjemu 800 1 na ha. Po vyhranění herbicídnych príznakov na testovacích rastlinách sa bonitá-ciou určil stupeň herbicidneho účinku. PREDMET VYNÁLEZU 1. 2,6-dimetylfenylkarbamoylmetylpyridíniumchlorid obecného vzorca I ,ch3 x Cl° O— nh-co-ch2-n^J> (li
- 2. Spflsob přípravy látky podlá bodu 1 obecného vzorca I vyznačený tým, že N-chlóracetyl-2,6-dimetylanilín obecného vzorca II ΤΎ)-NH—CO—CH2CI (II) CH-t reaguje s pyridínom obecného vzorca III (III) v molárnom pomere 0,7 až 1,3 molu v prostředí cyklohexánu pri teplotě 0 °C až 80 °C po dobu1 až 10 hodin.
- 3. SpĎsob podlá bodu 2 vyznačený tým, že sa reakcia uskutočňuje po dobu 1 až 4 hodinpri teplote 0 °C až 30 °C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS871433A CS263363B1 (en) | 1987-03-04 | 1987-03-04 | 2,6-dimethylphenylcarbamoylmethylpyridiniumchloride and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS871433A CS263363B1 (en) | 1987-03-04 | 1987-03-04 | 2,6-dimethylphenylcarbamoylmethylpyridiniumchloride and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS143387A1 CS143387A1 (en) | 1988-09-16 |
| CS263363B1 true CS263363B1 (en) | 1989-04-14 |
Family
ID=5348684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS871433A CS263363B1 (en) | 1987-03-04 | 1987-03-04 | 2,6-dimethylphenylcarbamoylmethylpyridiniumchloride and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS263363B1 (cs) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12195428B2 (en) | 2019-03-11 | 2025-01-14 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12303496B2 (en) | 2019-11-06 | 2025-05-20 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20210143791A (ko) * | 2019-03-11 | 2021-11-29 | 녹시온 테라퓨틱스 인코포레이티드 | 하전된 이온 채널 차단제 및 사용 방법 |
-
1987
- 1987-03-04 CS CS871433A patent/CS263363B1/cs unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12195428B2 (en) | 2019-03-11 | 2025-01-14 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12303496B2 (en) | 2019-11-06 | 2025-05-20 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
Also Published As
| Publication number | Publication date |
|---|---|
| CS143387A1 (en) | 1988-09-16 |
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