CS263363B1 - 2,6-Dimethylphenylcarbamoylmethylpyridinium chloride and its preparation - Google Patents
2,6-Dimethylphenylcarbamoylmethylpyridinium chloride and its preparation Download PDFInfo
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Abstract
Riešenie sa týká 2,6-dimetylfenylkarbamoylmetylpyridíniumchlor idu, ktorý nebol doteraz opísáný (vzorec I). Látka sa připravuje reakciou N-chlóracetyl-2,6- -dimetylanilínu (vzorec II) s pyridínom. Uvedená látka vykazuje herbicídne účinky.The solution relates to 2,6-dimethylphenylcarbamoylmethylpyridinium chloride, which has not been described so far (formula I). The substance is prepared by reacting N-chloroacetyl-2,6-dimethylaniline (formula II) with pyridine. The substance has herbicidal effects.
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
263363 2
The subject of the invention is a herbicidally active 2,6-dimethylphenylcarbamoylmethylpyridinium chloride preparation thereof. It is known from the literature that N-chloroacetyl-2,6-dialkylaniline derivatives are herbicides, fungicides and growth regulators. (Chupp JP, CH 643 530, Moser H., Vogel CH., EP 115 470, Vogel CH., US 4,283,221, Ranny Co, Jp. Kokai 5,984,852).
We have now found that the compound of formula I
(18 is prepared by a process consisting of reacting N-chloroacetyl-2,6-dimethylaniline with a pyridine in a cyclohexane environment while warming the room for three hours.
The following example further explains, but does not limit, the preparation of the sub-invention compound. EXAMPLE 1 2,6-Dimethylphenylcarbamoylmethylpyridinium chloride 25 cm @ 3 of cyclohexane with 0.1 mol (19.8 g) of N-chloroacetyl-2,6-dimethylaniline are stirred in a three-necked flask equipped with a stirrer, a reflux condenser and a dropping funnel. 0.1 mol (8 cm) of dry pyridine is added dropwise to the solution3. After stirring for 2 hours at room temperature in the reaction medium, an oil is formed which rapidly solidifies. The crude product crystallized from ether, mp 98-100 ° C. Yield 85%. Formula: C15H17N2OC1M: 276.74 Analysis: Off. % C: 65.70% H: 5.19% H: 4.97% N: 10.12% N: 9.95% Cl: 12.81% Cl: 12, 56
The herbicidal effect of a compound of the invention
Compound of the Invention Dose 1 dose per 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 Hetachlor 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)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CS871433A CS263363B1 (en) | 1987-03-04 | 1987-03-04 | 2,6-Dimethylphenylcarbamoylmethylpyridinium chloride and its preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CS871433A CS263363B1 (en) | 1987-03-04 | 1987-03-04 | 2,6-Dimethylphenylcarbamoylmethylpyridinium chloride and its preparation |
Publications (2)
Publication Number | Publication Date |
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CS143387A1 CS143387A1 (en) | 1988-09-16 |
CS263363B1 true CS263363B1 (en) | 1989-04-14 |
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CS871433A CS263363B1 (en) | 1987-03-04 | 1987-03-04 | 2,6-Dimethylphenylcarbamoylmethylpyridinium chloride and its preparation |
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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 |
---|---|---|---|---|
JP7692834B2 (en) * | 2019-03-11 | 2025-06-16 | ノシオン セラピューティクス,インコーポレイテッド | Charged ion channel blockers and methods of use - Patents.com |
-
1987
- 1987-03-04 CS CS871433A patent/CS263363B1/en 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 |
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CS143387A1 (en) | 1988-09-16 |
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