DE1921468A1 - Substituted ureas - Google Patents
Substituted ureasInfo
- Publication number
- DE1921468A1 DE1921468A1 DE19691921468 DE1921468A DE1921468A1 DE 1921468 A1 DE1921468 A1 DE 1921468A1 DE 19691921468 DE19691921468 DE 19691921468 DE 1921468 A DE1921468 A DE 1921468A DE 1921468 A1 DE1921468 A1 DE 1921468A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- methyl
- substituted ureas
- hydrogen
- methylurea
- 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
- 235000013877 carbamide Nutrition 0.000 title claims description 8
- 150000003672 ureas Chemical class 0.000 title claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 5
- 241000209094 Oryza Species 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 235000008427 Brassica arvensis Nutrition 0.000 description 4
- 244000024671 Brassica kaber Species 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 240000006122 Chenopodium album Species 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 4
- 240000006694 Stellaria media Species 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 235000007244 Zea mays Nutrition 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 240000004585 Dactylis glomerata Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000004296 Lolium perenne Species 0.000 description 2
- 244000292693 Poa annua Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- -1 methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- ABXVZVIOAYTALB-UHFFFAOYSA-N (3-nitrophenyl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=CC([N+]([O-])=O)=C1 ABXVZVIOAYTALB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000209048 Poa Species 0.000 description 1
- 240000006597 Poa trivialis Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
1 Q 9 1 A R 81 Q 9 1 A R 8
Badische Anilin- & Soda-Pabrik AG IO^Badische Anilin- & Soda-Pabrik AG IO ^
Unser Zeichen: 0.Z. 26 I65 Schs/Be/O 6700 Ludwigshafen, 25.April 1969 Our reference: 0.Z. 26 I65 Schs / Be / O 6700 Ludwigshafen, April 25, 1969
Substituierte HarnstoffeSubstituted ureas
Die vorliegende Erfindung betrifft neue wertvolle substituierte Harnstoffe und diese enthaltende Herbizide.The present invention relates to new valuable substituted ureas and herbicides containing them.
Es ist bekannt, substituierte Harnstoffe, z.B. den N-p-Chlorphenyl-N^N'-dimethylharnstoff, als herbizide Mittel zu verwenden. Diese Mittel haben jedoch den Nachteil verschiedene Kulturpflanzen, z.B. Getreide und Reis, zu schädigen.It is known to use substituted ureas, e.g. N-p-chlorophenyl-N ^ N'-dimethylurea, to be used as herbicidal agents. However, these means have the disadvantage of different crops, e.g. grain and rice.
Es wurde gefunden, daß substituierte Harnstoffe der FormelIt has been found that substituted ureas of the formula
in der R1 Wasserstoff, die Methylgruppe oder die Gruppe -CONHRf-, wobei Rc5 eine niedere Alkylgruppe bedeutet (Methyl, Äthyl, Propyl, Isopropyl, Butyl), R2 Wasserstoff oder die Methylgruppe, R-, Wasserstoff oder eine niedere Alkylgruppe (Methyl, Äthyl, Propyl, Isopropyl) und R2^ einen gegebenenfalls durch Halogen (Chlor, Brom), Alkoxyl (Methoxy, Äthoxy, Propoxy, Isopropoxy), Cyan oder Alkylmercapto (Methylmercapto, Äthylmercapto) substituierten aliphatischen Rest (Methyl, Äthyl, Propyl, Isopropyl, Butyl, seco Butyl, Isobutyl, tert.-Butyl, Pentyl, Hexyl, 1,3-Dimethylbutyl, Allyl, Butin-l-yl-3, Methyl-3-butin-l-yl-J) bedeuten, eine gute herbizide Wirkung bei guter Verträglichkeit an Reis, Mais und σ> Weizen zeigen.in which R 1 is hydrogen, the methyl group or the group -CONHRf-, where Rc 5 is a lower alkyl group (methyl, ethyl, propyl, isopropyl, butyl), R 2 is hydrogen or the methyl group, R-, hydrogen or a lower alkyl group ( Methyl, ethyl, propyl, isopropyl) and R 2 ^ an aliphatic radical (methyl, ethyl, propyl) optionally substituted by halogen (chlorine, bromine), alkoxyl (methoxy, ethoxy, propoxy, isopropoxy), cyano or alkyl mercapto (methyl mercapto, ethyl mercapto) , Isopropyl, butyl, sec o butyl, isobutyl, tert-butyl, pentyl, hexyl, 1,3-dimethylbutyl, allyl, butyn-1-yl-3, methyl-3-butyn-1-yl-I) mean, show a good herbicidal effect with good tolerance to rice, maize and σ> wheat.
Die neuen substituierten Harnstoffe können beispielsweise durch «ο Reduktion von substituiertem Nitrobenzol mit Zinkstaub, Umsetzung des Reduktionsproduktes mit einem Methylisocyanat und Alkylierung 197/69 · - 2 -The new substituted ureas can for example by «Ο Reduction of substituted nitrobenzene with zinc dust, implementation of the reduction product with a methyl isocyanate and alkylation 197/69 - 2 -
192U68192U68
- 2 - O.Z. 26 165- 2 - O.Z. 26 165
des entstandenen Hydroxyharnstoffs mit einem Alkylierungsmittel, ■ beispielsweise Dimethylsulfat, hergestellt werden.the resulting hydroxyurea with an alkylating agent, ■ for example dimethyl sulfate.
Die folgenden Versuchsangaben erläutern die Herstellung der erfindungsgemäßen Verbindungen.The following experimental data explain the preparation of the inventive Links.
42 Teile (Gewichtsteile) (3-Dimethylcarbamoyloxy)-nitrobenzol und 4,3 Teile Ammonchlorid werden in 50 Teilen Wasser und 100 Teilen Äthanol suspendiert bzw. gelöst und durch portionsweise Zugabe von 34 Teilen Zinkstaub bei 70° C reduziert. Nach dem Abfiltrieren der Zinksalze wird das Filtrat eingeengt, der Rückstand in 100 Teilen Äthylenchlorid gelöst, die Lösung mit Wasser gewaschen, getrocknet und erneut vom Lösungsmittel befreit. Zu dem verbliebenen Rückstand gibt man 100 Teile Toluol und versetzt die Lösung bei Raumtemperatur mit 8,6 Teilen Methylisocyanat. Der ausgefallene Niederschlag wird abgesaugt und getrocknet. Man erhält 34 Teile N-3-Dimethylcarbamoyloxyphenyl-N-hydroxy-N1-methy!harnstoff j Fp 98°C.42 parts (parts by weight) of (3-dimethylcarbamoyloxy) nitrobenzene and 4.3 parts of ammonium chloride are suspended or dissolved in 50 parts of water and 100 parts of ethanol and reduced at 70 ° C. by adding 34 parts of zinc dust in portions. After the zinc salts have been filtered off, the filtrate is concentrated, the residue is dissolved in 100 parts of ethylene chloride, the solution is washed with water, dried and again freed from the solvent. 100 parts of toluene are added to the remaining residue, and 8.6 parts of methyl isocyanate are added to the solution at room temperature. The deposited precipitate is filtered off with suction and dried. 34 parts of N-3-dimethylcarbamoyloxyphenyl-N-hydroxy-N 1 -methy! Urea j mp 98 ° C. are obtained.
12,65 Teile N-3-Dimethylcarbamoyloxyphenyl-N-hydroxy-N'-methylharnstoff werden in 100 Teilen Wasser suspendiert und bei Raumtemperatur mit einer Lösung von 6 Teilen Natriumhydroxyd, gelöst in 20'Teilen Wasser, versetzt. Zu der Lösung tropft man bei einer Temperatur von 25 bis 500C 12,6 Teile Dimethylsulfat. Anschließend hält man das Gemisch neon einige Zeit bei einer Temperatur von 500C. Das ausgefallene öl wird mit Methylenchlorid ausgeschüttelt und dann das Lösungsmittel isn 7skuuSä entfernt. Man erhält 10,5 Teile N-^-DimethylcarbamoyloxypheajX-N-methoxy-N'-methylharnstoff; njp 1,5403. 12.65 parts of N-3-dimethylcarbamoyloxyphenyl-N-hydroxy-N'-methylurea are suspended in 100 parts of water and a solution of 6 parts of sodium hydroxide dissolved in 20 parts of water is added at room temperature. 12.6 parts of dimethyl sulfate are added dropwise to the solution at a temperature of 25 to 50 ° C. Then holding the mixture neon some time at a temperature of 50 0 C. The precipitated oil is extracted with methylene chloride and then the solvent isn 7skuuSä removed. 10.5 parts of N - ^ - dimethylcarbamoyloxypheajX-N-methoxy-N'-methylurea are obtained; njp 1.5403.
Die übrigen Wirkstoff können nach entsprechenden Yepfahren hergestellt werden. Nachfolgend werden einige Wirkstoff genannt: N-3-Methylcarbamoyloxyphenyl-N-hydroxy-N'-methylharnstoff N-3-tert. Butyloarbamoyloxyphenyl-N-hydroxy-N1-methylharnstoff N-3-Methylcarbamoyloxyphenyl-N-methylcarbamoyloxy-N'-methy!harnstoff The other active ingredients can be prepared according to the corresponding Yepverfahren. Some active ingredients are mentioned below: N-3-methylcarbamoyloxyphenyl-N-hydroxy-N'-methylurea N-3-tert. Butyloarbamoyloxyphenyl-N-hydroxy-N 1 -methylurea, N-3-methylcarbamoyloxyphenyl-N-methylcarbamoyloxy-N'-methylurea
N-3-Isopropylcarbamoyloxyphenyl-N-hydroxy-N1,N'-dimethyl-harnstoff .N-3- [^-Methoxy-propyl-carbamoyloxyJ -phenyl-N-hydroxy-N1-methylharnstoff 009846/1989 N-3-Isopropylcarbamoyloxyphenyl-N-hydroxy-N 1 , N'-dimethyl-urea. N-3- [^ -Methoxy-propyl-carbamoyloxy] -phenyl-N-hydroxy-N 1 -methyl urea 009846/1989
192U68192U68
- 3 - 0.2. 26 165- 3 - 0.2. 26 165
N-3- r5-Methyl-butin-l-yl-(3)-carbamoyloxyJ -phenyl-N-hydroxy-N1 -methylhamstof fN -3- r5-methyl-butyn-1-yl- (3) -carbamoyloxyJ -phenyl-N-hydroxy-N 1 -methylurea f
N-J- ("ß-chlorHthyl-carbamoyloxyj -phenyl-N-methylcarbamoyloxy-N'-methylharnstoff N-J- ("ß-chloroHthyl-carbamoyloxyj -phenyl-N-methylcarbamoyloxy-N'-methylurea
Die erfindungsgemäßen Herbizide können als Lösungen, Emulsionen, Suspensionen oder Stäubemittel angewendet werden. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollen in jedem Fall eine feine Verteilung der wirksamen Substanz gewährleisten. The herbicides according to the invention can be used as solutions, emulsions, suspensions or dusts. The forms of application depend entirely on the intended use; You should ensure a fine distribution of the active substance in each case.
Zur Herstellung von direkt versprühbaren Lösungen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie öle pflanzlichen oder tierischen Ursprungs, außerdem cyclische Kohlenwasserstoffe, wie Tetrahydronaphthalin und alkylierte Naphthaline in Betracht.Mineral oil fractions are used to produce solutions that can be sprayed directly with a medium to high boiling point, such as kerosene or diesel oil, as well as coal tar oils and oils of vegetable or animal origin Origin, also cyclic hydrocarbons such as tetrahydronaphthalene and alkylated naphthalenes into consideration.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulvern) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen können die Substanzen als solche oder in einem Lösungsmittel gelöst, mittels Netz- oder Dispergiermitteln in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Emulgier- oder Dispergiermittel und eventuell Lösungsmittel bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders) by adding water be prepared. To produce emulsions, the substances can be used as such or dissolved in a solvent, by means of Wetting agents or dispersants are homogenized in water. But it can also consist of active substances, emulsifiers or dispersants and possibly solvent-based concentrates are prepared which are suitable for dilution with water.
Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Dusts can be produced by mixing or grinding the active substances can be produced with a solid carrier.
Ein Zusatz von Insektiziden, Fungiziden, Bakteriziden, Wachstumsregulatoren und anderen Herbiziden ist ebenso möglich wie die Mischung mit Düngemitteln.An addition of insecticides, fungicides, bactericides, growth regulators and other herbicides is just as possible as mixing with fertilizers.
Die folgenden Beispiele zeigen die Anwendung der erfindungsgemäßen Mittel.The following examples show the application of the invention Middle.
009846/1989009846/1989
192U68192U68
O.Z. 26 165O.Z. 26 165
Im Gewächshaus wurde in Versuchstöpfe lehmhaltiger Tonboden eingefüllt und die Samen von Oryza sativa (Reis), Zea mays (Mais, Triticum vulgäre (Weizen), Poa annua, Poa trivialis, Dactylis glomerata, Sinapis arvensis, Chenopodium album und Stellaria media eingesät. Der so vorbereitete Boden wurde mit je 5 ^g je ha der folgenden Wirkstoffe N-3-Dimethylcarbamoyloxyphenyl-N-hydroxy-N1-methylharnstoff (i) und im Vergleich dazu mit N-p-Chlorphenyl-N1-dimethylharnstoff (II) jeweils dispergiert in 500 Liter Wasser je ha, behandelt. Nach 4 Wochen wurde festgestellt, daß der Wirkstoff I bei gleich guter herbizider Wirkung eine wesentlich bessere Verträglichkeit als II an Oryza sativa, Zea mays und Triticum vulgäre zeigte.In the greenhouse, clay soil was poured into test pots and the seeds of Oryza sativa (rice), Zea mays (maize, Triticum vulgare (wheat), Poa annua, Poa trivialis, Dactylis glomerata, Sinapis arvensis, Chenopodium album and Stellaria media were sown Prepared soil was dispersed in 500 with 5 ^ g per hectare of the following active ingredients N-3-dimethylcarbamoyloxyphenyl-N-hydroxy-N 1 -methylurea (i) and, in comparison, with Np-chlorophenyl-N 1 -dimethylurea (II) Liters of water per hectare.After 4 weeks it was found that the active ingredient I, with the same good herbicidal action, was significantly better tolerated than II on Oryza sativa, Zea mays and Triticum vulgare.
Das Versuchsergebnis ist aus nachfolgender Tabelle zu ersehen:The test result can be seen from the following table:
Nutzpflanzen Oryza sativa Zea mays Triticum vulgäre Unerwünschte Pflanzen Poa annua Poa trivialis Dactylis glomerata Useful plants Oryza sativa Zea mays Triticum vulgare Undesirable plants Poa annua Poa trivialis Dactylis glomerata
Sinapis arvensis Chenopodium album Stellaria mediaSinapis arvensis Chenopodium album Stellaria media
0 = ohne Schädigung 100 β totale Schädigung0 = without damage 100 β total damage
Die Pflanzen Oryza sativa (Reis), Echinochloa crus-galli, Poa annua, Lolium perenne, Chenopodium album, Stellaria media und Sinapis arvensis wurden bei einer Wuchshöhe von 3-18 cm mit je 2 kgThe plants Oryza sativa (rice), Echinochloa crus-galli, Poa annua, Lolium perenne, Chenopodium album, Stellaria media and Sinapis arvensis were 3-18 cm tall and weighed 2 kg each
00984 6/1989 · _5_00984 6/1989 · _ 5 _
192H68192H68
- 5 - ■ O.Z. 26 165- 5 - ■ O.Z. 26 165
♦je ha der folgenden Wirkstoffe N-3-Dimethylcarbamoyloxyphenyl-N-hydroxy-N'-methylharnstoff (i) und im Vergleich dazu mit N-p-Chlorphenyl-N*-dimethylharnstoff (II) behandelt, jeweils dispergiert in 500 Liter Wasser je ha. Nach 3-4 Wochen zeigte der Wirkstoff I im Vergleich zu II eine bessere Reisverträglichkeit bei gleich guter herbizider Wirkung.♦ per hectare of the following active ingredients N-3-dimethylcarbamoyloxyphenyl-N-hydroxy-N'-methylurea (i) and in comparison with N-p-chlorophenyl-N * -dimethylurea (II) treated, each dispersed in 500 liters of water per hectare. After 3-4 weeks the active ingredient showed I compared to II better tolerance to rice with the same good herbicidal effect.
Wirkstoff I IIActive ingredient I II
Oryza sativa 10 65Oryza sativa 10 65
Unerwünschte Pflanzen Echinochloa crus-galli Poa. annua
Lolium perenne
Chenopodium album
Stellaria media
Sinapis arvensis Unwanted plants Echinochloa crus-galli Poa. annua
Lolium perenne
Chenopodium album
Stellaria media
Sinapis arvensis
0 = ohne Schädigung 100 = totale Schädigung0 = no damage 100 = total damage
009846/1989009846/1989
Claims (2)
Substituierte Harnstoffe der Formel Claims
Substituted ureas of the formula
F=7 OR1 r NV-NCN;
F = 7 OR 1
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691921468 DE1921468A1 (en) | 1969-04-26 | 1969-04-26 | Substituted ureas |
| AU14271/70A AU1427170A (en) | 1969-04-26 | 1970-04-23 | Substituted ureas |
| NL7005946A NL7005946A (en) | 1969-04-26 | 1970-04-23 | |
| GB1980870A GB1298122A (en) | 1969-04-26 | 1970-04-24 | Substituted ureas |
| BE749489D BE749489A (en) | 1969-04-26 | 1970-04-24 | SUBSTITUTED UREES |
| FR7015321A FR2040276A1 (en) | 1969-04-26 | 1970-04-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691921468 DE1921468A1 (en) | 1969-04-26 | 1969-04-26 | Substituted ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1921468A1 true DE1921468A1 (en) | 1970-11-12 |
Family
ID=5732547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691921468 Pending DE1921468A1 (en) | 1969-04-26 | 1969-04-26 | Substituted ureas |
Country Status (6)
| Country | Link |
|---|---|
| AU (1) | AU1427170A (en) |
| BE (1) | BE749489A (en) |
| DE (1) | DE1921468A1 (en) |
| FR (1) | FR2040276A1 (en) |
| GB (1) | GB1298122A (en) |
| NL (1) | NL7005946A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3670010A (en) * | 1969-05-06 | 1972-06-13 | Stauffer Chemical Co | Trifluoromethyl acylated urea carbamates |
-
1969
- 1969-04-26 DE DE19691921468 patent/DE1921468A1/en active Pending
-
1970
- 1970-04-23 AU AU14271/70A patent/AU1427170A/en not_active Expired
- 1970-04-23 NL NL7005946A patent/NL7005946A/xx unknown
- 1970-04-24 BE BE749489D patent/BE749489A/en unknown
- 1970-04-24 GB GB1980870A patent/GB1298122A/en not_active Expired
- 1970-04-27 FR FR7015321A patent/FR2040276A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU1427170A (en) | 1971-10-28 |
| NL7005946A (en) | 1970-10-28 |
| GB1298122A (en) | 1972-11-29 |
| BE749489A (en) | 1970-10-26 |
| FR2040276A1 (en) | 1971-01-22 |
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