DE1568203B - Process for the preparation of N phenyl N methyl N (2 3 dibromo I methyl allyl) ureas - Google Patents
Process for the preparation of N phenyl N methyl N (2 3 dibromo I methyl allyl) ureasInfo
- Publication number
- DE1568203B DE1568203B DE1568203B DE 1568203 B DE1568203 B DE 1568203B DE 1568203 B DE1568203 B DE 1568203B
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- dibromo
- phenyl
- allyl
- ureas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von N-Phenyl-N'-methyl-N'-(2,3-dibrom-l-methylallyl)-harnstoffen der allgemeinen FormelThe invention relates to a method of manufacture of N-phenyl-N'-methyl-N '- (2,3-dibromo-l-methylallyl) ureas of the general formula
,CH3 , CH 3
—CO—N^ (I)—CO — N ^ (I)
"CH-CBr=CHBr"CH-CBr = CHBr
CH3 CH 3
in der X Chlor oder Brom und η die Zahl 1 oder 2 bedeuten kann.in which X can be chlorine or bromine and η can be 1 or 2.
Das Verfahren ist dadurch gekennzeichnet, daß man ein Harnstoffderivat der allgemeinen FormelThe process is characterized in that a urea derivative of the general formula
CH3 CH 3
X-X-
NH-CO—NNH-CO-N
αϊ)αϊ)
" CH-C=CH CH3 "CH-C = CH CH 3
in der X und η die oben bezeichneten Bedeutungen besitzen, mit äquimolaren Mengen Brom umsetzt.in which X and η have the meanings given above, reacts with equimolar amounts of bromine.
Bei der Einwirkung von Chlor kann aus Verbindungen der allgemeinen Formel II keine einheitliche Substanz erhalten werden. Die Verbindungen der allgemeinen Formel II werden vielmehr durch das Chlor zerstört, überraschenderweise führt die Bromierung der Verbindungen der allgemeinen Formel II zu einheitlichen Produkten, die in praktisch quantitativer Ausbeute erhalten werden können.When exposed to chlorine, compounds of the general formula II cannot be made uniform Substance to be preserved. The compounds of general formula II are rather by the chlorine destroys, surprisingly, the bromination of the compounds of the general formula results II to uniform products which can be obtained in practically quantitative yield.
Der glatte und einheitliche Verlauf der Reaktion konnte im vorliegenden Fall deshalb nicht vorausgesehen werden, weil die zu bromierenden Ausgangsprodukte andere reaktionsfähige Stellen aufweisen,The smooth and uniform course of the reaction could therefore not be foreseen in the present case because the starting products to be brominated have other reactive sites,
ίο an denen ein Eintritt des Broms hätte erwartet
werden müssen. Insbesondere konnte der glatte Verlauf der Bromierung nicht vorausgesehen werden.
. Die Bromierung kann in indifferenten organischen Lösungsmitteln, wie z. B. Chloroform, Tetrachlorkohlenstoff
oder Eisessig, bei Temperaturen, die vorzugsweise zwischen —5 bis +300C liegen, durchgeführt
werden.ίο at which the occurrence of the bromine should have been expected. In particular, the smooth course of the bromination could not be foreseen.
. The bromination can be carried out in inert organic solvents, such as. B. chloroform, carbon tetrachloride or glacial acetic acid, at temperatures which are preferably between -5 to +30 0 C, are carried out.
Die nach dem erfindungsgemäßen Verfahren erhaltenen Verbindungen sind wertvolle Pflanzenschutzmittel mit ausgezeichneter selektiv-herbizider Wirkung. The compounds obtained by the process according to the invention are valuable crop protection agents with excellent selective herbicidal effect.
Die Ausgangsprodukte können nach bekannten Verfahren, insbesondere gemäß deutscher Patentschrift 1 108 977, durch Umsetzung von aromatischen Isocyanaten mit Butinylaminen oder von aromatischen Aminen mit N-Methyl-N-butinylcarbaminsäurederivaten hergestellt werden. Der Reaktionsverlauf läßt sich durch folgendes Schema wiedergeben :The starting products can be prepared according to known processes, in particular according to German patent specification 1 108 977, by reaction of aromatic isocyanates with butynylamines or of aromatic amines with N-methyl-N-butynylcarbamic acid derivatives getting produced. The course of the reaction can be shown by the following scheme :
CH3 CH 3
H_N / H _ N /
CH3 CH 3
CH3 CH 3
- NH — CO — N- NH - CO - N
— C = CH- C = CH
CH3 CH 3
/r\/ r \
NH2 + Cl- C-NNH 2 + Cl-CN
O CH-C = CHO CH-C = CH
säurebindendes Mittel <f/ V- NH — CO — Nacid binding agent <f / V- NH - CO - N
CH3 CH 3
SCH — C = CH
CH3 S CH - C = CH
CH 3
Folgende Verbindungen können beispielsweise nach dem erfindungsgemäßen Verfahren hergestellt werden:The following compounds can be produced, for example, by the method according to the invention:
N-(4-Chlor-phenyl)-N'-methyl-N- (4-chloro-phenyl) -N'-methyl-
N'-(2,3-dibrom-l-methyl-allyl)-harnstoff; N-(3-Chlor-phenyl)-N'-methyl-N '- (2,3-dibromo-1-methyl-allyl) urea; N- (3-chloro-phenyl) -N'-methyl-
N'-(2,3-dibrom-l-methyl-allyl)-harnstoff; N-(3,4-Dichlor-phenyl)-N'-methyl-N '- (2,3-dibromo-1-methyl-allyl) urea; N- (3,4-dichloro-phenyl) -N'-methyl-
N'-(2,3-dibrom-l-methyl-allyl)-harnstoff; N-(4-Brom-phenyl)-N'-methyl-N'-(2,3-dibrom-l -methyl-allyl)-hamstoff.N '- (2,3-dibromo-1-methyl-allyl) urea; N- (4-Bromo-phenyl) -N'-methyl-N '- (2,3-dibromo-l methyl allyl urea.
Das folgende Beispiel soll das erfindungsgemäße Verfahren erläutern: .The following example is intended to explain the method according to the invention:.
Herstellung von N-(4-Chlor-phenyl)-N'-methyl-N'-(2,3-dibrom-l-methyl-allyl)-harnstoff Preparation of N- (4-chloro-phenyl) -N'-methyl-N '- (2,3-dibromo-1-methyl-allyl) -urea
80 g Brom werden innerhalb von 6 Stunden zu einer Lösung von 118,2 g N-(4-Chlor-phenyl)-N'-methyl-N'-isobutinylharnstoff in Chloroform bei 00C zugetropft. Anschließend wird das Reaktionsgemisch 1 Stunde bei Raumtemperatur gehalten. Danach wird das Lösungsmittel abdestilliert und der Rückstand mit Toluol gewaschen. Man erhält nach dem Umkristallisieren aus Äthanol 188 g N-(4-Chlor-phenyl)-N'-methyl-N'-(2,3-dibrom-l-methyl-allyl)-harnstoff mit dem F. 198° C (Zersetzung).80 g of bromine over 6 hours to a solution of 118.2 g of N- (4-chloro-phenyl) -N'-methyl-N'-isobutinylharnstoff in chloroform at 0 0 C was added dropwise. The reaction mixture is then kept at room temperature for 1 hour. The solvent is then distilled off and the residue is washed with toluene. After recrystallization from ethanol, 188 g of N- (4-chlorophenyl) -N'-methyl-N '- (2,3-dibromo-1-methyl-allyl) urea with a melting point of 198 ° C ( Decomposition).
Claims (2)
CH3 CH-CBr = CHBr
CH 3
A=/ \ <f \ —NH-CO-i /
A = / \
Family
ID=
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