CS263363B1 - 2,6-dimethylphenylcarbamoylmethylpyridiniumchloride and process for preparing thereof - Google Patents

2,6-dimethylphenylcarbamoylmethylpyridiniumchloride and process for preparing thereof Download PDF

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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
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CS
Czechoslovakia
Prior art keywords
formula
chloroacetyl
dimethylaniline
dimethylphenylcarbamoylmethylpyridiniumchloride
hours
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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 idu who has not been previously described (Formula I). substance is prepared by reaction of N-chloroacetyl-2,6- dimethylaniline (Formula II) with pyridine. Said substance exhibits herbicidal effects.

Description

Predmetom vynálezu je herbicídne účinný 2,6-dimetylfenylkarbamoylmetylpyridíniumchlorid a jeho spdsob pripravy. Z literatúry je známe, že deriváty N-chlóracetyl-2,6-dialkylanilínov sú herbicidy, fungicidy a regulátory rastu. (Chupp J. P., CH 643 530, Moser H., Vogel CH.,The present invention relates to herbicidally active 2,6-dimethylphenylcarbamoylmethylpyridinium chloride and a process for its preparation. It is known in the literature that N-chloroacetyl-2,6-dialkylanilines derivatives are herbicides, fungicides and growth regulators. (Chupp J.P., CH 643 530, Moser H., Vogel CH.,

EP 115 470, Vogel CH., US 4 283 221, Kanneho Co,, Jpn. Kokai 5 984 852).EP 115 470, Vogel CH., US 4,283,221, Kanne Co, Jpn. Kokai 5,984,852).

Teraz sme zistill, že látka obecného vzorca IWe have now found that the compound of formula I

(18 sa připravuje spůsobom, ktorý spočívá v reakcii N-chlóracetyl-2,6-dimetylanilínu s pyridínom v prostředí cykiohexánu pri teplote miestnosti po dobu troch hodin.(18 is prepared by a method of reacting N-chloroacetyl-2,6-dimethylaniline with pyridine in cyclohexane at room temperature for three hours.

Nasledujúci příklad bližšie vysvětluje, ale nijako neobmedzuje přípravu zlúčeniny podlá vynálezu.The following example illustrates in more detail, but does not limit the preparation of the compound of the invention.

Přiklad 1Example 1

2,6-dimetylfenylkarbamoylmetylpyridíniumchlorid2,6-dimetylfenylkarbamoylmetylpyridíniumchlorid

V trojhrdlovej banke opatrenej miešadlom, spatným chladičom a prikvapkávacim lievikom, sa mieša 25 cm3 cykiohexánu s 0,1 mol (19,8 g) N-chlóracetyl-2,6-dimetylanilínom. Do roztoku 3 sa prikvapká 0,1 mol (B cm ) suchého pyridinu. Po dvojhodinovom miešaní pri teplote miestnosti z reakčného prostredia sa vylúči olej, ktorý rýchlo tuhne. Surový produkt kryštalizujeIn a three-necked flask equipped with a stirrer, a reflux condenser and an addition funnel, 25 cm 3 of cyclohexane are mixed with 0.1 mol (19.8 g) of N-chloroacetyl-2,6-dimethylaniline. 0.1 mol (B cm) of dry pyridine was added dropwise to solution 3. After stirring at room temperature for 2 hours, an oil precipitated from the reaction medium and solidified rapidly. The crude product crystallizes

z éteru, t.t. 98 až 100 °C. Výťažok 85 %. from ether, m.p. 98-100 ° C. Yield 85%. Sumárny vzorec: C15H17N2OC1Summary formula: C 15 H 17 N 2 OCl M: 276,74 M: 276.74 Analýza: Vyp. % C: 65,70 Analysis: Off. % C: 65.70 Zist.: % C: 65,35 Found:% C: 65.35 % H: 5,19 % H: 5.19 % H: 4,97 % H: 4.97 » N: 10,12 N: 10.12 « N: 9,95 N: 9.95 « Cl: 12,81 Cl: 12.81 % Cl: 12,56 % Cl: 12.56

Herbicídny účinok zlúčeniny podlá vynálezuThe herbicidal effect of a compound of the invention

Zlúčenina podlá vynálezu compound according to the invention Dávka úč. 1. na ha Batch Account. First per ha Echinochloa erus-galli Echinochloa ERUs-galli 1 1 5,0 5.0 5 5 3,5 3.5 5 5 2,5 2.5 5 5 1.75 1.75 4 4 1,25 1.25 4 4 0,875 0,875 3,5 3.5 0,625 0,625 2,5 2.5 Metachlór metolachlor 5,0 5.0 5 5 (Standard) (Standard) 3,5 3.5 5 5 2,5 2.5 5 5 1,75 1.75 5 5 1,25 1.25 4,5 4.5 0,875 0,875 4 4 0,625 0,625 4 4

pokračovánie tabulkycontinued table

Zlúčenina podlá vynálezu A compound of the invention Dávka úč, 1. na ha Batch Account, 1. per ha Echinochloa crus-galli Echinochloa crus-galli Chlórtoluron chlorotuloron 5,0 5.0 3 3 (Standard) (Standard) 3,5 3.5 2,5 2.5 2,5 2.5 2,5 2.5 1,75 1.75 2,5 2.5 1,25 1.25 0 0 0,875 0,875 0 0 0,625 0,625 0 0

Bonitačný stupeň: 2 - rastliný zretelne atakované, 3 - rastliny značné atakované,Breeding level: 2 - plant clearly attacked, 3 - plants strongly attacked,

- rastliny ťažko atakované, 5 - rastliny uhynuté.- plants heavily attacked, 5 - plants dead.

Pracovný postup: Do nádob naplněných neošetrenou pieskovitohlinitou půdou sa vysiali semená testovacích rastíín. Po urovnaní a zavlažení povrchu půdy následovala aplikácia odstupňovaných vodných koncentrácii testovaných látok. Objem aplikačného roztoku zodpovedal objemu 800 1 na ha. Po vyhranění herbicídnych príznakov na testovacích rastlinách sa bonitáciou určil stupeň herbicídneho účinku.Procedure: Seed crops of test plants were sown in containers filled with untreated sandy loam soil. The leveling and irrigation of the soil surface was followed by application of graduated aqueous concentrations of the test substances. The volume of application solution was 800 l / ha. After elimination of the herbicidal symptoms on the test plants, the degree of herbicidal effect was determined by bonitation.

Claims (3)

1. 2,6-dimetylfenylkarbamoylmetylpyridíniumchlorid obecného vzorca I ,ch3 x Cl°1. 2,6-dimethylphenylcarbamoylmethylpyridinium chloride of general formula I, ch 3 x Cl ° O— nh-co-ch2-n^J>O-nh-co-ch 2 -n 2 (I)(I) 2. Spůsob přípravy látky podlá bodu 1 obecného vzorca I vyznačený tým, že N-chlóracetyl -2,6-dimetylanilín obecného vzorca II (Q)-NH—CO—CHjCI (II)2. A process according to claim 1, characterized in that N-chloroacetyl-2,6-dimethylaniline of formula II (Q) -NH-CO-CH2Cl2 (II) CH, reaguje s pyridínom obecného vzorca III (III) v molárnom pomere 0,7 až 1,3 molu v prostředí cyklohexánu pri teplote 0 °C až 80 °C po dobu 1 až 10 hodin.CH 2 is reacted with pyridine of formula III (III) at a molar ratio of 0.7 to 1.3 moles in cyclohexane at 0 ° C to 80 ° C for 1 to 10 hours. 3. Spůsob podlá bodu 2 vyznačený tým, že sa reakcia uskutočňuje po dobu 1 až 4 hodin pri teplote 0 °C až 30 °C.3. Process 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-dimethylphenylcarbamoylmethylpyridiniumchloride and process for preparing thereof 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

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* 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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