CS263363B1 - 2,6-Dimethylphenylcarbamoylmethylpyridinium chloride and its preparation - Google Patents

2,6-Dimethylphenylcarbamoylmethylpyridinium chloride and its preparation Download PDF

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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
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Czechoslovakia
Prior art keywords
plants
formula
attacked
dimethylphenylcarbamoylmethylpyridinium
chloride
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CS871433A
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Czech (cs)
Slovak (sk)
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CS143387A1 (en
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Anna Doc Rndr Csc Gvozdjakova
Stefan Rndr Csc Varkonda
Vaclav Rndr Csc Konecny
Olga Rndr Csc Hyblova
Original Assignee
Gvozdjakova Anna
Varkonda Stefan
Konecny Vaclav
Olga Rndr Csc Hyblova
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Application filed by Gvozdjakova Anna, Varkonda Stefan, Konecny Vaclav, Olga Rndr Csc Hyblova filed Critical Gvozdjakova Anna
Priority to CS871433A priority Critical patent/CS263363B1/en
Publication of CS143387A1 publication Critical patent/CS143387A1/en
Publication of CS263363B1 publication Critical patent/CS263363B1/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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)

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> (li263363 Table of the Invention Compounds of the Invention Dose of Ingredients, 1. per ha Echinochloa crus-galli Chlorotoluron 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 Bonitation degree: 2 - plants clearly attacked, 3 - plants highly attacked, 4 - plants heavily attacked, 5 - plants dead. Workflow: Test plants were seeded in containers filled with untreated sand-aluminum soil. After leveling and irrigating the surface of the soil, application of graded aqueous concentrations of the test substances followed. The volume of the application solution was 800 l per ha. After determining the herbicidal symptoms on the test plants, the degree of herbicidal effect was determined by the creditworthiness. OBJECT OF THE INVENTION 1. 2,6-Dimethylphenylcarbamoylmethylpyridinium chloride of formula I, ch3 x Cl0 O-nh-co-ch2-n ^ J > 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.2. A process for the preparation of a compound according to claim 1, characterized in that the N-chloroacetyl-2,6-dimethylaniline of formula (II) -NH-CO-CH2Cl (II) CH-t is reacted with a pyridine of formula (III) (III) in a molar ratio of 0.7 to 1.3 mol in cyclohexane at 0 ° C to 80 ° C for 1 to 10 hours. 3. SpĎsob podlá bodu 2 vyznačený tým, že sa reakcia uskutočňuje po dobu 1 až 4 hodinpri teplote 0 °C až 30 °C.Method according to claim 2, characterized in that the reaction is carried out for 1 to 4 hours at a temperature of 0 ° C to 30 ° C.
CS871433A 1987-03-04 1987-03-04 2,6-Dimethylphenylcarbamoylmethylpyridinium chloride and its preparation CS263363B1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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

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