DE2012508A1 - QuaternSre ammonium salts - Google Patents

Description

PATENT ADVERTISER DSL HANS-QUNTHBH EGGERT, DIPLOMA CHEMIST

5 EDLNUNDBNTHAL PBTKK-EINTGtN-STITASSI 2 2012508

Cologne, March 16, 1970 Eg / pz / 56

ügine Kuhlmann * Io rue du Qen6ral Foy, Paris! 8e / Frankreloh

Quaternary ammonium salts

The invention relates to new quaternary ammonium salts the general formula

• ^R 1 Ar 4 0 ~ R ~ JL) ", nX

in which Ar is a polyhalogenated aromatic radical, such as a pentachlorophenyl, Ootaohiordiphenyl-, Octabromdiphenylen-j Hexaohlordibromodiphenylen-, Dodecachlorterphenyä lenrtet,

R, ύ ^ " Rg, fL" inen aliphatisohen, cycloallphatlachen or arylaliphAtieohen reet, which may have other substituents or iii heteroato "such as 0 or 3, for example" white, ethyl, ieopropyl- , 'i-chloroethyl, allyl, ethyllyl, ben »ri-. Chlorbwiiyl-, Morphelyl-, Mtthyl% ia «ill ^ lr« st,

X "tin anion, .ttii a * a» «e» i4-, Allcylmilfatanion .it M. 2o Konlenetoffato ^ n tsiü IiI Aryleulfenatanion iihd η a ganae number Veh 1 iil j bleuten. -

BADORiGINAL 009839/2306

m 2 -

The invention also relates to a process for the preparation of these quaternary ammonium salts, which is characterized in that a tertiary amine has the structure

Ar f ~ O - R - N) _n

R ₂

with an alkylating agent of the formula K ₁ JL , where Ar, R, R ,, R ₂ * R ** X and N have the meaning mentioned. This reaction can be carried out in the presence of an inert solvent.

The for the preparation of the new compounds according to the invention suitable amines can be prepared in a simple manner by the process of German patent application P 19 22 278.7 will.

The solvent can be an excess of the alkylation agent IUX, but inert solvents, such as benzene, monochlorobenzene, dioxane, carbon tetrachloride and the like can be used.

The process conditions depend largely on the nature of the reactants, in particular on the alkylation "! Ttil tUX au" The reaction proceeds when using allylehleri * raseh, but slowly when using chloroXthane, but is slow when using chloroXthane. The temperature is generally determined by the HÜ boiling point of the solvent. This · t * «p # * temperature can, however, be increased if under pressure: gürbel *. is tet. The reaction is carried out in allgeeeinen s * Ü "hsn 5o and 250 ^0C.

009839/2306

BATH ORIGINAL

The new quaternary ammonium salts according to the invention are suitable as active ingredients for pesticides, especially as bactericides and fungicides They can be used as such. However, they are preferably used in the form of preparations such as Emulsions, PölVern * fasting öd ^ granules a »

The quaternary ammonium salts of the present invention are used the iteöfc ^

Example 1 . ■■■■. . '; · ~ ^ ~ Yi; ^:::.: \: _. :;:

125 g

W, 5; g N ^ N ^ Diraeti ^ lH * anoiaiain> M g HaOK i ^ platelets "- form and -; ^ io- ßm ^ Dioatan introduced" During hours ^ uin boiling was accomplished & tr, d & n & ek £ ^ l trierfc and the marine mixture neutralized with COg. Older obtained liieäer & ohx ^ Dekantiereii stit destii liierter pig * gewasöiieii and then in methylene chloride ^: Me. I ^ simg.wmHfe- ^ ingeäainiift ^ wot ^ "tt ^ i fine -

Condensation product with a content of% S chlorine and%> 1 % Stiökstorf were obtained "

: Example ■ & . '"■■' ■ .."; ■ -:>'; / - ^; v ■ ";V."

150 g of A13.ylöhl © rio and 60 g of the apiine derivative obtained were heated for 5 hours on the e _. -

eish im ^ erliatii * der Reaictioii. all-, Ätoldihlen, KiifctiFiereii · ^ ind _t Trocjcnen les -iligäersöiilass was ^ ö ^ g of a whitejci powder, th, · Μδ ^: -Γ-ΐΒ: .-- Α- ^ ο & οαν ^ ηο / βϊ »ΤΑδ water that was soluble iind

ionizable chlorine

nitrogen Qesantohlor

Xq / loo g

47.1 %

This product consisted essentially of the quaternary Annoniua salt of the structure.

CH,

-CH ₂ -N -.CH ₂ -CH ₂ -

CH ₂ -CH ₂

-CH ₂ -CH- OH ₂ , 2 Cl '

Example 3

A mixture of 57 g of the Aain prepared in Example 1 and 150 g of 1,2-DiohlorMthane were on for 10 hours RÜokfluss heated. After cooling, the reaction mixture was treated with Xther and lingered on this catfish put dichloroXthane and anine away. The one left behind pasty solid was washed nit Xther and then few trooknet. 30 g of a solid were obtained which essentially consisted of the internal appearance of the structure

Cl CH ₂ -OH ₂ - JT CH ₂ -CH ₂ - 0 _to

- CH ₂ -CH ₂ Cl, 2

009839/2306

duration. This solid showed the following analysis values

ionizable chlorine ο, 221 eq / loo g nitrogen 3 * 59 %

Oesamtohlor content 5o.3 % Example 4

142.5 g of hexachlorobenzene, 445 g of N, N ~ bimethylethanolamine, 28 g of NaOH in platethene form and 500 onr dioxane introduced. It was for 3 1/2 hours heated to boiling and the reaction mixture then treated in the same way as in Example 1. To this Finally, N, N-dimethylamino ~ 2 «ethoxy ~ pentachlorobenzene was obtained.

Example 5

A mixture of 60 g of the product obtained in Example 4 with 120 g of allyl chloride was refluxed for 10 hours * heats. After cooling, 72 ß were one by filtration structure white solid

₂ -CHg - H ** - * CH ₂ ·· CH - CHg,

separated, which showed the following analytical values:

ionizable chlorine 0.23 eq / loo g

Nitrogen>, 4 % Oesamtohlor content 5o, l % Ethylene groups * 0.27 eq / loo g

009839/23 0 6

Claims (1)

Claims 1. Quaternary ammonium salts of the general formula Ar -4- 0 - R -N) _n , in the Ar a polyhalogenous aromatic residue, R, R-j, Rp, R-, an aliphatic, an cycloaliphatic compound or arylaliphatic radical which optionally has substituents or a heteroatom, in particular O or S, X "is an anion and η is an integer from 1 to 3. 2. Quaternary ammonium salts according to claim 1, characterized in that they are a pentaohlophenyl, octachlorodiphenyl, ootabromodiphenylene, hexachlorodibromodiphenylene, dodecaterphenylene radical as the radical Ar, and a methyl, ethyl, isopropyl radical as the radicals R, R ,, Rg * R- * -, ~ ß-chloroethyl, allyl, methallyl, benzyl, chlorobenzyl, morpholyl _T or methylthioethyl and as anion X ~ a halide, alkylsulfonate anion with up to 20 carbon atoms or an arylsulfonate anion exhibit. Process for the production of quaternary ammonium salts according to claim 1 or 2, characterized in that that one has a tertiary amine of the structure 009839/2306 Ar «f. O -R -H) _n with an alkylating agent of the formula R, X reacts,. where the radicals Ar, R, R ₁ , R ₂ * R ^ * X and η have the meaning mentioned. Λ. Method according to claim 3, characterized in that the reaction in the presence of the alkylating agent R, X performs as a solvent. 5 * The method according to claim 3, characterized in that dafl the reaction is carried out in the presence of an inert solvent, in particular benzene, monochlorobenzene, dioxane or carbon tetrachloride. 6. The method according to claim 5, characterized in that the reaction is carried out between 5o and 250.degree. 7. Use of quaternary ammonium salts according to claim 1 or "2 as pesticides * G09S39 / 2306