DE1117561B - Process for the production of urea derivatives - Google Patents
Process for the production of urea derivativesInfo
- Publication number
- DE1117561B DE1117561B DEF31340A DEF0031340A DE1117561B DE 1117561 B DE1117561 B DE 1117561B DE F31340 A DEF31340 A DE F31340A DE F0031340 A DEF0031340 A DE F0031340A DE 1117561 B DE1117561 B DE 1117561B
- Authority
- DE
- Germany
- Prior art keywords
- urea derivatives
- production
- cyanomethyl
- isocyanate
- compounds
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 150000003672 ureas Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- -1 aryl isocyanates Chemical class 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- MCLITRXWHZUNCQ-UHFFFAOYSA-N methylcyanamide Chemical class CNC#N MCLITRXWHZUNCQ-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- PVVRRUUMHFWFQV-UHFFFAOYSA-N 2-(methylamino)acetonitrile Chemical compound CNCC#N PVVRRUUMHFWFQV-UHFFFAOYSA-N 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical class NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 1
- OLBJNSPBWLCTOT-UHFFFAOYSA-N 2,4-dichloro-1-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C(Cl)=C1 OLBJNSPBWLCTOT-UHFFFAOYSA-N 0.000 description 1
- DAYCWCMZFOMJDW-UHFFFAOYSA-N 2-(2-methylpropylamino)acetonitrile Chemical compound CC(C)CNCC#N DAYCWCMZFOMJDW-UHFFFAOYSA-N 0.000 description 1
- SPMMZKAWNAKPJM-UHFFFAOYSA-N 2-(butylamino)acetonitrile Chemical compound CCCCNCC#N SPMMZKAWNAKPJM-UHFFFAOYSA-N 0.000 description 1
- VXAOLDZFARINGE-UHFFFAOYSA-N 2-(ethylamino)acetonitrile Chemical compound CCNCC#N VXAOLDZFARINGE-UHFFFAOYSA-N 0.000 description 1
- YOEHYACECVSKEQ-UHFFFAOYSA-N 2-(propylamino)acetonitrile Chemical compound CCCNCC#N YOEHYACECVSKEQ-UHFFFAOYSA-N 0.000 description 1
- KOOCPROKRWKLJI-UHFFFAOYSA-N 2-(tert-butylamino)acetonitrile Chemical compound CC(C)(C)NCC#N KOOCPROKRWKLJI-UHFFFAOYSA-N 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N allylamine Natural products NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 230000008216 juvenile development Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1836—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from derivatives of carbamic acid
- C07C273/1845—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from derivatives of carbamic acid comprising the -N-C(O)-Hal moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Harnstoffderivaten Die herbizide Wirksamkeit von N-Phenyl-N'-alkyl-N'-carboxymethyl-harnstoffen ist bereits bekannt.Process for the preparation of urea derivatives Herbicidal effectiveness of N-phenyl-N'-alkyl-N'-carboxymethyl ureas is already known.
Es wurde nun gefunden, daß man durch Umsetzung von Arylisocyanaten oderArylcarbaminsäurechloriden, die im Kern durch Alkyl- bzw. Alkoxyreste oder Chlor substituiert sein können, mit Cyanomethylaminen zu Harnstoffderivaten gelangt, die sich durch eine überraschende, ausgesprochen selektive Wirkung als Unkrautvernichtungsmittel auszeichnen. Als für die genannte Umsetzung geeignete Arylisocyanate seien beispielsweise genannt: Phenylisocyanat, p-Chlorphenylisocyanat, 3,4-Dichlorphenylisocyanat, 2,4-Dichlorphenylisocyanat, p-Methylisocyanat, p-Methoxyphenylisocyanat. Unter Cyanomethylaminen sind vor allem Verbindungen mit einem gesättigten oder ungesättigten Alkylrest mit I bis 4 C-Atomen zu verstehen, wie z. B. Cyanomethylamin, Cyanomethyl-methylamin, Cyanomethyl-butylamin, Cyanomethyl-isobutylamin, Cyanomethyl-tert.-butylamin, Cyanomethyl-äthylamin, Cyanomethyl-propylamin, Cyanomethyl-allylamin. It has now been found that by reacting aryl isocyanates orArylcarbamic acid chlorides, the nucleus by alkyl or alkoxy radicals or chlorine can be substituted, with cyanomethylamines to obtain urea derivatives that has a surprising, extremely selective effect as a herbicide distinguish. Examples of suitable aryl isocyanates for the reaction mentioned are named: phenyl isocyanate, p-chlorophenyl isocyanate, 3,4-dichlorophenyl isocyanate, 2,4-dichlorophenyl isocyanate, p-methyl isocyanate, p-methoxyphenyl isocyanate. Among the most important are cyanomethylamines Compounds with a saturated or unsaturated alkyl radical with 1 to 4 carbon atoms to understand how B. cyanomethylamine, cyanomethyl-methylamine, cyanomethyl-butylamine, Cyanomethyl-isobutylamine, cyanomethyl-tert-butylamine, cyanomethyl-ethylamine, cyanomethyl-propylamine, Cyanomethyl allylamine.
Die erfindungsgemäß erhältlichen Harnstoffderivate stellen im allgemein gut kristallisierte Verbindungen dar. The urea derivatives obtainable according to the invention generally represent well crystallized compounds.
Unter Unkräutern, die mit Hilfe der verfahrensgemäß erhältlichen Verbindungen bekämpft werden können, sollen dabei im weitesten Sinne des Wortes Pflanzen verstanden werden, die an Stellen aufwachsen, wo sie unerwünscht sind. Die erfindungsgemäß herstellbaren Substanzen wirken bereits in geringerer Konzentration als Herbizide, wobei sich die Wirkung vornehmlich gegen keimende Samen richtet, d. h., die Samen keimen normal, und die Sämlinge zeigen eine normale Jugendentwicklung. 10 bis 14 Tage nach der Keimung sterben die Pflanzen jedoch unter Chlorose-und Welkerscheinungen ab. Auch bei einer Postemergence-Spritzung gelingt bei geeigneter Wahl der Konzentration an Wirkstoff die Vernichtung der Pflanzen. In Gewächshausversuchen wurde aber nun gefunden, daß sich die verfahrensgemäßen Produkte überraschenderweise besonders zur selektiven Unkrautbekämpfung eignen. Among weeds that can be obtained with the aid of the Connections can be combated, should in the broadest sense of the word Plants are understood that grow in places where they are undesirable. The substances which can be prepared according to the invention are already effective in a lower concentration as herbicides, whereby the effect is primarily directed against germinating seeds, d. that is, the seeds germinate normally and the seedlings show normal juvenile development. However, 10 to 14 days after germination, the plants die with symptoms of chlorosis and wilting away. With a suitable choice of concentration, a post-emergence spray is also successful in active ingredient the destruction of the plants. In greenhouse trials, however, was now found that the products according to the process are surprisingly special suitable for selective weed control.
Die Unkrautvernichtungsmittel können dabei sowohl einen als auch mehrere Vertreter der obengenannten Verbindungsklasse enthalten. Sie werden mit einem festen oder flüssigen Streckmittel ausgebracht. The herbicides can be either one or the other contain several representatives of the above-mentioned class of compounds. They will with a solid or liquid extender applied.
Der Zusatz bekannter Herbizide ist dabei möglich.The addition of known herbicides is possible.
Wäßrige Dispersionen, Emulsionen oder Lösungen der genannten Wirkstoffe können Netzmittel, Emulgatoren oder andere Dispergierhilfsmittel enthalten.Aqueous dispersions, emulsions or solutions of the active ingredients mentioned may contain wetting agents, emulsifiers or other dispersing aids.
Die Ausbringung erfolgt im Spritz-, Stäube- oder Streuverfahren.The application is carried out by spraying, dusting or littering.
Die herbizide Wirksamkeit der erfindungsgemäßen Verbindungen im Vergleich zu analog gebauten bekannten Stoffen sei durch die folgenden Gewächshausversuche erläutert: Gemischte Aussaaten von Gossypium, Sinapis, Chenopodium, Hordeum, Zea und Soleum werden post-emergence (24 Stunden nach der Aussaat) mit einer bestimmten Aufwandmenge der verschiedenen Unkrautbekämpfungsmittel behandelt und bei sechs Schädigungsgraden das Wachstum der einzelnen Pflanzenarten bonitiert (0 = keine Wirkung, 5 = totale Vernichtung). Die Ergebnisse der entsprechenden Versuche sind aus der nachfolgenden Tabelle ersichtlich. The herbicidal activity of the compounds according to the invention in comparison The following greenhouse experiments can be used to describe known materials constructed in the same way explained: Mixed sowing of Gossypium, Sinapis, Chenopodium, Hordeum, Zea and brine will be post-emergence (24 hours after sowing) with a certain Application rate of the various weed control agents and treated at six Degree of damage the growth of the individual plant species is rated (0 = none Effect, 5 = total annihilation). The results of the corresponding tests are can be seen in the following table.
Wie aus der Tabelle hervorgeht, zeichnen sich die erfindungsgemäßen Verbindungen 1 und 2 gegenüber den bekannten Substanzen 3 und 4 durch eine größere Selektivität aus. Die Präparate 1 und 2 sind in hervorragendem Maße zur selektiven Unkrautbekämpfung in Baumwoll- und Maiskulturen geeignet. As can be seen from the table, the inventive Compounds 1 and 2 compared to the known substances 3 and 4 by a larger one Selectivity off. Preparations 1 and 2 are excellent for selective use Suitable for weed control in cotton and maize crops.
Die nachfolgenden Beispiele erläutern die Herstellung einiger Vertreter der erfindungsgemäß nach dem beanspruchten Verfahren erhältlichen Verbindungen: Beispiel 1 Zu 20 g Methylaminoacetonitril fügt man unter Kühlung bei 10 bis 20"C 35,6 g Phenylisocyanat. Nach beendeter Reaktion wird die gebildete kristalline Substanz aus Benzol umkristallisiert. Man erhält in fast quantitativer Ausbeute N-Phenyl-N'-methyl-N'-cyanomethyl-harnstoff. F. 103 bis 104°C. The following examples explain the production of some representatives of the compounds obtainable according to the invention by the claimed process: EXAMPLE 1 20 g of methylaminoacetonitrile are added with cooling at 10 to 20 ° C 35.6 grams of phenyl isocyanate. After the completion of the reaction, the formed crystalline substance becomes recrystallized from benzene. You get in almost quantitative yield N-phenyl-N'-methyl-N'-cyanomethyl urea. M.p. 103 to 104 ° C.
Analyse: CloHllN3o.Analysis: CloHllN3o.
Molgewicht 189.Molecular weight 189.
Berechnet ... H 5,87, C 63,54, N22,23; gefunden ... H5,87, C63,22, N21,92. Calculated ... H 5.87, C 63.54, N22.23; found ... H5.87, C63.22, N21.92.
Beispiel 2 Zu 15 g Methylaminoacetonitril tropft man bei 10 bis 20"C eine Lösung von 33 g p-Chlorphenylisocyanat in 200 ccm Benzol. Man erhält N-(p-Chlorphenyl)-N'-methyl-N'-cyanomethyl-harnstoff vom F.110°C. Example 2 15 g of methylaminoacetonitrile are added dropwise at 10 to 20 ° C a solution of 33 g of p-chlorophenyl isocyanate in 200 cc of benzene. N- (p-chlorophenyl) -N'-methyl-N'-cyanomethylurea is obtained from 110 ° C.
Analyse: C10H10N3OCl.Analysis: C10H10N3OCl.
Molgewicht 223,5.Molecular weight 223.5.
Berechnet ... C 53,74, H 4,51; gefunden .. C 53,63, H 4,59. Calculated ... C 53.74, H 4.51; found .. C 53.63, H 4.59.
Auf analoge Weise erhält man aus Methylaminoacetonitril und 3,4-Dichlorphenylisocyanat, das in Chlorbenzol gelöst ist, den N-(3,4-Dichlorphenyl)-N'-methyl-N'-cyanomethyl-harnstoff vom F. 162 bis 163°C. In an analogous manner, from methylaminoacetonitrile and 3,4-dichlorophenyl isocyanate, which is dissolved in chlorobenzene, the N- (3,4-dichlorophenyl) -N'-methyl-N'-cyanomethyl urea from 162 to 163 ° C.
Analyse: CloH9N3oCl2-Molgewicht 258.Analysis: CloH9N3oCl2 molecular weight 258.
Berechnet ... C 46,55, H 3,52, N 16,29, Cl 27,49; gefunden ... C
46,82, H 3,46, N I5,98, C127,73.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31340A DE1117561B (en) | 1960-05-31 | 1960-05-31 | Process for the production of urea derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31340A DE1117561B (en) | 1960-05-31 | 1960-05-31 | Process for the production of urea derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1117561B true DE1117561B (en) | 1961-11-23 |
Family
ID=7094139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31340A Pending DE1117561B (en) | 1960-05-31 | 1960-05-31 | Process for the production of urea derivatives |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1117561B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0417256A4 (en) * | 1989-04-03 | 1991-09-25 | The Nutrasweet Company | Novel n-(sulfomethyl)-n'-arylureas |
-
1960
- 1960-05-31 DE DEF31340A patent/DE1117561B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0417256A4 (en) * | 1989-04-03 | 1991-09-25 | The Nutrasweet Company | Novel n-(sulfomethyl)-n'-arylureas |
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