DE1542834C - N-phenyl-N-hydroxyurea esters and their use as herbicides - Google Patents
N-phenyl-N-hydroxyurea esters and their use as herbicidesInfo
- Publication number
- DE1542834C DE1542834C DE19661542834 DE1542834 DE1542834C DE 1542834 C DE1542834 C DE 1542834C DE 19661542834 DE19661542834 DE 19661542834 DE 1542834 DE1542834 DE 1542834 DE 1542834 C DE1542834 C DE 1542834C
- Authority
- DE
- Germany
- Prior art keywords
- hydroxyurea
- phenyl
- methyl
- herbicides
- dichlorophenyl
- 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.)
- Expired
Links
- 239000004009 herbicide Substances 0.000 title claims description 4
- MTFFANYLEXKMTD-UHFFFAOYSA-N 1-hydroxy-1-phenylurea Chemical class NC(=O)N(O)C1=CC=CC=C1 MTFFANYLEXKMTD-UHFFFAOYSA-N 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims description 8
- -1 N-phenyl-N'-hydroxyurea ester Chemical class 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- AAVSQBMWOCNSDL-UHFFFAOYSA-N 1-hydroxy-3-phenylurea Chemical class ONC(=O)NC1=CC=CC=C1 AAVSQBMWOCNSDL-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 244000292693 Poa annua Species 0.000 description 11
- 235000009108 Urtica dioica Nutrition 0.000 description 10
- 240000006122 Chenopodium album Species 0.000 description 9
- 240000005979 Hordeum vulgare Species 0.000 description 9
- 235000007340 Hordeum vulgare Nutrition 0.000 description 9
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 8
- 240000006694 Stellaria media Species 0.000 description 8
- 244000274883 Urtica dioica Species 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 244000024671 Brassica kaber Species 0.000 description 7
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 240000001592 Amaranthus caudatus Species 0.000 description 6
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 6
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 6
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 6
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 6
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 6
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 241001621841 Alopecurus myosuroides Species 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 235000008427 Brassica arvensis Nutrition 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 235000009344 Chenopodium album Nutrition 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- 241001148683 Zostera marina Species 0.000 description 4
- 229960001330 hydroxycarbamide Drugs 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 3
- 235000005637 Brassica campestris Nutrition 0.000 description 3
- 235000014750 Brassica kaber Nutrition 0.000 description 3
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 3
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- 244000082988 Secale cereale Species 0.000 description 3
- 235000007238 Secale cereale Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000018914 Galinsoga parviflora Nutrition 0.000 description 2
- 244000214240 Galinsoga parviflora Species 0.000 description 2
- 241001456088 Hesperocnide Species 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 229940087195 2,4-dichlorophenoxyacetate Drugs 0.000 description 1
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000010662 Bidens pilosa Nutrition 0.000 description 1
- 244000104272 Bidens pilosa Species 0.000 description 1
- 244000144786 Chrysanthemum segetum Species 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 241000110847 Kochia Species 0.000 description 1
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 1
- 244000303225 Lamium amplexicaule Species 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 241001465363 Panicum capillare Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 244000037751 Persicaria maculosa Species 0.000 description 1
- 241001313099 Pieris napi Species 0.000 description 1
- 235000004442 Polygonum persicaria Nutrition 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001714 carbamic acid halides Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
Description
Es ist bekannt, trisubstituierte Harnstoffe, z. B. N-p-Chlorphenyl-N'.N'-dimethylharnstoff. als herbizide Wirkstoffe zu verwenden. Ihre Wirkung befriedigt jedoch nicht.It is known to use trisubstituted ureas, e.g. B. N- p -chlorophenyl-N'.N'-dimethylurea. as herbicidal Use active ingredients. However, their effect is not satisfactory.
Es wurde gefunden, daß N-Phenyl-N'-hydroxyharnstoff-Ester der allgemeinen FormelIt has been found that N-phenyl-N'-hydroxyurea esters the general formula
Rückstand wird aus Toluol—Petroläther umkristallisiert. Man erhält 21 Gewichtsteile N-3,4-Dichlorphenyl - N' - methyl - N' - (2,4 - dichlorphenoxyacet)-oxyharnstoff der StrukturformelThe residue is recrystallized from toluene-petroleum ether. 21 parts by weight of N-3,4-dichlorophenyl - N '- methyl - N' - (2,4 - dichlorophenoxyacet) oxyurea are obtained the structural formula
/CH,/ CH,
CO-NCO-N
CH3
OCO-RCH 3
OCO-R
ClCl
NH-CO-N ·NH-CO-N
ClCl
in der X01=D ein Fluor-, Chlor- oder Bromatom, eine Trifluormethyl- oder Nitrogruppe in 3- oder 4-Stellung oder X(n=2) Chloratome in 3,4-Stellung darstellt und R die Bedeutung eines Dimethylamino-, i-Propyl-, Isopropenyl-, 2-Chlor-n-butyl-(2)-, Bromt-butyl-, 3-n-Heptyl-, Cyclopropyl- oder 2,4-Dichlorphenoxymethylrestes hat, einen schnellen Wirkungseintritt und eine gute herbizide Wirkung an Unkräutern und Ungräsern zeigen.in which X 01 = D a fluorine, chlorine or bromine atom, a trifluoromethyl or nitro group in the 3- or 4-position or X (n = 2) chlorine atoms in the 3,4-position and R represents a dimethylamino, i-propyl, isopropenyl, 2-chloro-n-butyl- (2) -, bromot-butyl, 3-n-heptyl, cyclopropyl or 2,4-dichlorophenoxymethyl radicals, has a rapid onset of action and is good herbicidal Show effect on weeds and grass weeds.
Die Wirkstoffe können in an sich bekannter Weise durch Umsetzung von substituierten N-Phenyl-N'-hydroxyharnstoffen mit Säurehalogeniden bzw. Carbaminsäurehalogeniden in Gegenwart alkalischer Mittel hergestellt werden, wobei die N-Phenyl-N'-hydroxyharnstoffe ihrerseits z. B. aus den entsprechenden Isocyanaten und substituierten Hydroxylaminen hergestellt werden können.The active ingredients can be prepared in a manner known per se by reacting substituted N-phenyl-N'-hydroxyureas with acid halides or carbamic acid halides in the presence of alkaline Means are made with the N-phenyl-N'-hydroxyureas on their part z. B. from the corresponding isocyanates and substituted hydroxylamines can be produced.
Die folgenden Herstellungsverfahren erläutern die Herstellung der neuen substituierten Harnstoffderivate. The following production processes explain the production of the new substituted urea derivatives.
Zu 12 Gewichtsteilen N - 3,4 - Dichlorphenyl-N'-methyl-N'-hydroxyharnstoff, gelöst in 75 Gewichtsteilen Toluol und 5,2 Gewichtsteilen Triäthylamin, tropft man unter Rühren bei 35° C 5,4 Gewichtsteile Dimethylcarbaminsäurechlorid. Anschließend wird das Reaktionsgemisch noch einige Stunden bei 60 bis 65° C gehalten. Nach dem Abkühlen wird das Gemisch mit Wasser gewaschen, getrocknet und im Vakuum vom Lösungsmittel befreit. Der kristalline Rückstand wird aus Toluol umkristallisiert. Man erhält 14 Gewichtsteile N-3,4-Dichlorphenyl-N'-methyl-N'-(dimethylcarbamoyl)-oxyharnstoff der StrukturformelTo 12 parts by weight of N - 3,4 - dichlorophenyl-N'-methyl-N'-hydroxyurea, dissolved in 75 parts by weight of toluene and 5.2 parts by weight of triethylamine, 5.4 parts by weight of dimethylcarbamic acid chloride are added dropwise at 35 ° C. with stirring. Subsequently the reaction mixture is kept at 60 to 65 ° C for a few hours. After cooling it will the mixture is washed with water, dried and freed from the solvent in vacuo. the crystalline residue is recrystallized from toluene. 14 parts by weight of N-3,4-dichlorophenyl-N'-methyl-N '- (dimethylcarbamoyl) oxyurea are obtained the structural formula
'CH3 'CH 3
ι Cl
ι
vom F. 115 bis 117° C.
Chlor gefunden 32,4%, berechnet 32,4%.from 115 to 117 ° C.
Chlorine found 32.4%, calculated 32.4%.
Die übrigen Wirkstoffe können nach entsprechenden Verfahren hergestellt werden. Die Reaktionstemperatur bei der Veresterung kann dabei je nach Art des verwendeten Säurehalogenids oder Carbaminsäurehalogenids zwischen —20 und +10O0C liegen, vorzugsweise jedoch zwischen 0 und 70° C.The other active ingredients can be produced by appropriate processes. The reaction temperature in the esterification can, depending on the kind of the acid halide or Carbaminsäurehalogenids used are between -20 and + 10O 0 C, but preferably between 0 and 70 ° C.
Als erfindungsgemäße Verbindungen -werden die folgenden Substanzen genannt:
30 The following substances are mentioned as compounds according to the invention:
30th
4040
4545
O-CO-NO-CO-N
vom F. 134 bis 136° C.
Chlor gefunden 23,6%, berechnet 23,2%. .from 134 to 136 ° C.
Chlorine found 23.6%, calculated 23.2%. .
Zu 12 Gewichtsteilen N - 3,4 - Dichlorphenyl-N'-methyl-N'-hydroxyharnstoff, gelöst in 75 Gewichtsteilen Toluol und 5,2 Gewichtsteilen Triäthylamin, tropft man unter Rühren bei 20 bis 30° C 12 Gewichtsteile 2,4-Dichlorphenoxyessigsäurechlorid, gelöst in 10 Gewichtsteilen Toluol. Anschließend wird das Reaktionsgemisch noch einige Stunden bei 40 bis 45°C gehalten. Nach dem Abkühlen wird das Gemisch mit Wasser gewaschen, getrocknet und im Vakuum vom Lösungsmittel befreit. Der kristallineTo 12 parts by weight of N - 3,4 - dichlorophenyl-N'-methyl-N'-hydroxyurea, dissolved in 75 parts by weight of toluene and 5.2 parts by weight of triethylamine, 12 parts by weight are added dropwise with stirring at 20.degree.-30.degree 2,4-dichlorophenoxyacetic acid chloride, dissolved in 10 parts by weight of toluene. Then will the reaction mixture was kept at 40 to 45 ° C. for a few hours. After cooling down, this will be The mixture was washed with water, dried and freed from the solvent in vacuo. The crystalline one
-CH
^CH2 . / CHl
-CH
^ CH 2
— N
^CH3 / CH 3
- N
^ CH 3
^CH3 / CH 3
^ CH 3
— N
^CH3 / CH 3
- N
^ CH 3
Fortsetzungcontinuation
(- (
(
^CH3 /
^ CH 3
77 bis 80Kp-0.5 =
77 to 80
102 bis 104Κρ. Οι5 =
102 to 104
Die erfindungsgemäßen Verbindungen 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 compounds according to the invention can be used as solutions, emulsions, suspensions or dusts be applied. The forms of application depend entirely on the intended use; they should ensure a fine distribution of the active substance in each case.
Die erfindungsgemäßen Verbindungen können aber auch mit anderen Herbiziden, z. B. Triazinen, Dichloralkylcarbonsäurederivaten, Harnstoffen, Uracilen oder Pyridazonen gemeinsam zur Anwendung gelangen. However, the compounds according to the invention can also be used with other herbicides, e.g. B. triazines, dichloroalkylcarboxylic acid derivatives, Urea, uracil or pyridazone are used together.
Die folgenden Versuche erläutern die Anwendung der erfindungsgemäßen Herbizide.The following experiments explain the use of the herbicides according to the invention.
Im Gewächshaus wurden Kunststofftöpfe von 8 cm Durchmesser mit lehmigem Sandboden gefüllt und mit Samen von Gossypium spp. (Baumwolle), Zea mays (Mais), Hordeum vulgäre (Gerste), Triticum vulgäre (Weizen), Sinapis arvensis (Ackersenf), Chenopodium album (weißer Gänsefuß), Urtica urens (kleine Brennessel), Stellaria media (Vogelmiere), Galinsoga parvifiora (Franzosenkraut), Poa annua (einjähriges Rispengras) und Alopecurus myosuroides (Ackerfuchsschwanz) eingesät. Anschließend wurde der so vorbereitete Boden mit N-3,4-Dichlorphenyl-N' - methyl - N' - (dimethylcarbamoyl)- oxyharnstoff (I), N - 3,4 - Dichlorphenyl - N' - methyl - N' - (2,4 - dichlorphenoxyacetat)-oxyharnstoff (II) und im Vergleich dazu mit N - ρ - Chlorphenyl - Ν',Ν'- dimethylharnstoff (III) jeweils in einer Aufwandmenge von 3 kg Wirkstoff je Hektar dispergiert in 500 1 Wasser, behandelt. Nach 3 bis 4 Wochen wurde festgestellt, daß die Verbindungen I und II im Vergleich zu III eine etwa gleich gute herbizide Wirkung, jedoch eine bessere Verträglichkeit an Baumwolle, Mais, Gerste und Weizen besitzen. Die Versuchsergebnisse sind aus nachfolgender Tabelle zu ersehen.In the greenhouse, plastic pots 8 cm in diameter were filled with loamy sand soil and with seeds of Gossypium spp. (Cotton), Zea mays (maize), Hordeum vulgare (barley), Triticum vulgar (wheat), Sinapis arvensis (field mustard), Chenopodium album (white goose foot), Urtica urens (small nettle), Stellaria media (chickweed), Galinsoga parvifiora (French herb), Poa annua (annual bluegrass) and Alopecurus myosuroides (black foxtail) sown. Subsequently was the prepared soil with N-3,4-dichlorophenyl-N '- methyl - N' - (dimethylcarbamoyl) - oxyurea (I), N - 3,4 - dichlorophenyl - N '- methyl - N' - (2,4 - dichlorophenoxyacetate) oxyurea (II) and in comparison with N - ρ - chlorophenyl - Ν ', Ν'-dimethylurea (III) each at an application rate of 3 kg of active ingredient per hectare dispersed in 500 l of water, treated. After 3 to 4 weeks it was found that the compounds I and II compared to III an approximately equally good herbicidal effect, but better compatibility with cotton, maize, barley and own wheat. The test results can be seen from the table below.
II- active ingredient
II
0
10
50
0
10
5
0
5
0-50
0
5
0-5
20
30-40
40-5010-20
20th
30-40
40-50
90-100
100
90-100
90-100
90
80-9090-100
90-100
100
90-100
90-100
90
80-90
90-100
100
90-100
90-100
85-90
80-9090-100
90-100
100
90-100
90-100
85-90
80-90
90-100
100
90-100
90-100
90
80-90100
90-100
100
90-100
90-100
90
80-90
Kleine Brennessel
Vogelmiere White goosefoot
Small stinging nettle
Chickweed
Ackerfuchsschwanz ....Annual bluegrass
Black foxtail ....
0 = Ohne Schädigung.
100 = Totale Schädigung.0 = without damage.
100 = total damage.
Im Gewächshaus wurden die Pflanzen Zea mays (Mais), Hordeum vulgäre (Gerste), Triticum vulgäre (Weizen), Seeale cereale (Roggen), Sinapis arvensis (Ackersenf), Chenopodium album (weißer Gänsefuß), Urtica urens (kleine Brennessel), Bidens pilosa (Zweizahn), Kochia scoparia (Besenstaudich), Avena fatua (Flughafer), Poa annua (einjähriges Rispengras) und Alopecurus myosuroides (Ackerfuchsschwanz) bei einer Wuchshöhe von 4 bis 17 cm mit N - 3,4 - Dichlorphenyl - N' - methyl - N' - (dimethylcarbamoyl) - oxyharnstoff (I), N - 3,4 - Dichlorphenyl-N' - methyl - N' - (2,4 - dichlorphenoxyacet) - oxyharnstoff (II), N-3,4-Dichlorphenyl-N'-methyl-N'-(isobutyryl) - oxyharnstoff (III), N - 3,4 - Dichlorphenyl-N' - methyl - N' - (2 - chlor - 2 - methylbutanoyl) - oxyharnstoff (IV) und im Vergleich dazu mit N-p-Chlorphenyl-N',N'-dimethylharnstoff (V) in einer Menge von 3 kg Wirkstoff je Hektar, dispergiert in 500 1 Wasser, behandelt. Nach 3 bis 4 Wochen wurde festgestellt, daß die Verbindungen I, II, III und IV im Vergleich zu V eine stärkere herbizide Wirkung zeigten bei gleichzeitiger besserer Pflanzenverträglichkeit an Mais, Gerste, Weizen, Roggen. Die Versuchsergebnisse sind aus nachfolgender Tabelle zu ersehen: In the greenhouse, the plants were Zea mays (maize), Hordeum vulgare (barley), Triticum vulgare (Wheat), Seeale cereale (rye), Sinapis arvensis (field mustard), Chenopodium album (white goose foot), Urtica urens (small nettle), Bidens pilosa (two-toothed teeth), Kochia scoparia (broomstick), Avena fatua (Wild oats), Poa annua (annual bluegrass) and Alopecurus myosuroides (black foxtail) at a height of 4 to 17 cm with N - 3,4 - dichlorophenyl - N '- methyl - N' - (dimethylcarbamoyl) - oxyurea (I), N - 3,4 - dichlorophenyl-N '- methyl - N' - (2,4 - dichlorophenoxyacet) - oxyurea (II), N-3,4-dichlorophenyl-N'-methyl-N '- (isobutyryl) - oxyurea (III), N - 3,4 - dichlorophenyl-N' - methyl - N '- (2 - chloro - 2 - methylbutanoyl) - oxyurea (IV) and in comparison with N-p-chlorophenyl-N', N'-dimethylurea (V) in an amount of 3 kg of active ingredient per hectare, dispersed in 500 l of water. After 3 to 4 weeks it was found that the compounds I, II, III and IV compared to V have a stronger herbicidal action showed better plant tolerance on maize, barley, wheat and rye at the same time. The test results can be seen from the following table:
πιActive ingredient
πι
100
10
5-1010
5-10
0-100
0-10
1010
10
8090
80
0 = Ohne Schädigung.0 = without damage.
Fortsetzung1 542 834
continuation
IIIActive ingredient
III
100
90-100
100100
100
90-100
100
100
: 90-100
90100
100
: 90-100
90
100
90
8090-100
100
90
80
90-100
90-10090-100
90-100
90-100
100 "
90-100 ·
90-100 ■100
100 "
90-100
90-100 ■
90-100
90-10090
90-100
90-100
80-90
80-9080
80-90
80-90
100
90
90100
100
90
90
100
10090-100
100
100
90
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Ackerfuchsschwanz ...Annual bluegrass ...
Black foxtail ...
Eine Versuchsfläche, die mit Ackersenf (Sinapis arvensis), weißem Gänsefuß (Chenopodium album), kleiner Brennessel (Urtica urens), Vogelmiere (Stellaria media), Franzosenkraut (Galinsoga parviflora), einjährigem Rispengras (Poa annua) und Ackerfuchsschwanz (Alopecurus myosuroides) besät war, wurde am Tag der Saat mit N-^-Dichlorphenyl-N'-methyl-N'-(dimethylcarbamoyl)-oxyharnstoff (I) und im Vergleich dazu mit N-p-Chlorphenyl-N^N'-dimethylharnstoff (II) jeweils in einer Menge von 5 kg Wirkstoff je Hektar dispergiert in 500 1 Wasser, gespritzt. Während des Auflaufens der Unkräuter und Ungräser wurde festgestellt, daß nach 2 Wochen der Wirkstoff I die Unkräuter und Ungräser bereits abgetötet hat, während bei dem Wirkstoff II die Unkräuter und Ungräser erst nach 4 bis 5 Wochen vollkommen abgestorben waren.A test area filled with mustard (Sinapis arvensis), white goose foot (Chenopodium album), small nettle (Urtica urens), chickweed (Stellaria media), French herb (Galinsoga parviflora), annual Bluegrass (Poa annua) and black foxtail (Alopecurus myosuroides) was sown on the day of sowing with N - ^ - dichlorophenyl-N'-methyl-N '- (dimethylcarbamoyl) -oxyurea (I) and in comparison with N-p -chlorophenyl-N ^ N'-dimethylurea (II) each in an amount of 5 kg of active ingredient per hectare dispersed in 500 l of water, sprayed. During the emergence of the weeds and grass weeds, it was found that after 2 weeks the active ingredient I has already killed the weeds and grass weeds, while the active ingredient II the weeds and Weeds were only completely dead after 4 to 5 weeks.
Eine landwirtschaftliche Nutzfläche, die mit Ackersenf (Sinapis arvensis), weißem Gänsefuß (Chenopodium album), kleiner Brennessel (Urtica urens), Vogelmiere (Stellaria media), Franzosenkraut (Galinsoga parviflora), einjährigem Rispengras (Poa annua) und Ackerfuchsschwanz (Alopecurus myosuroides) bewachsen war, wurde bei einer Wuchshöhe der Unkräuter von 3 bis 8 cm mit N-3,4-Dichlorphenyl-N' - methyl - N' - (2,4 - dichlorphenoxyacet) - oxy harnstoff (II) jeweils in einer Menge von 5 kg Wirkstoff je Hektar dispergiert in 5001 Wasser, behandelt. Nach einigen Tagen konnte man beobachten, daß die Verbindung I gegenüber den Unkräutern und Ungräsern eine stärkere herbizide Wirkung zeigte als die Verbindung II. Nach 3 Wochen waren fast alle Pflanzen vollkommen abgestorben.An agricultural area covered with field mustard (Sinapis arvensis), white goosefoot (Chenopodium album), nettle (Urtica urens), chickweed (Stellaria media), French herb (Galinsoga parviflora), annual bluegrass (Poa annua) and black foxtail (Alopecurus myosuroides) was overgrown, with a height of the weeds of 3 to 8 cm with N-3,4-dichlorophenyl-N ' - methyl - N '- (2,4 - dichlorophenoxyacet) - oxy urea (II) each in an amount of 5 kg of active ingredient per hectare dispersed in 5001 of water, treated. After a few days you could see that the compound I showed a stronger herbicidal action against the weeds and grass weeds than compound II. After 3 weeks, almost all of the plants were completely dead.
Die Pflanzen Zea mays, Hordeum vulgäre, Triticum vulgäre, Oryza sativa, Echinochloa crus-galli, Setaria viridis, Panicum capillare, Poa annua, Alopecurus myosuroides, Matricaria chamomilla, Stellaria media, Polygonum persicaria, Chrysanthemum segetum, Solanum nigrum, Ipomoea purpurea und Lamium amplexicaule wurden bei einer Wuchshöhe von 3 bis 18 cm mit 2 kg/ha Wirkstoff N-p-Fluorphenyl-N' - methyl - N' - (dimethylcarbamoyl) - oxy harnst off I, dispergiert in 500 1 Wasser je Hektar, behandelt.The plants Zea mays, Hordeum vulgare, Triticum vulgare, Oryza sativa, Echinochloa crus-galli, Setaria viridis, Panicum capillare, Poa annua, Alopecurus myosuroides, Matricaria chamomilla, Stellaria media, Polygonum persicaria, Chrysanthemum segetum, Solanum nigrum, Ipomoea purpurea and Lamium amplexicaule were at a height of 3 to 18 cm with 2 kg / ha active ingredient N-p-fluorophenyl-N ' - methyl - N '- (dimethylcarbamoyl) - oxy urinst off I, dispersed in 500 liters of water per hectare, treated.
Nach 3 bis 4 Wochen wurde festgestellt, daß die unerwünschten Pflanzen stark und die Nutzpflanzen nur wenig geschädigt waren.After 3 to 4 weeks it was found that the undesirable plants were strong and the useful plants were only slightly damaged.
Claims (2)
1. N-Phenyl-N'-hydroxyharnstoff-Ester der allgemeinen FormelPatent claims:
1. N-phenyl-N'-hydroxyurea ester of the general formula
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1542834C true DE1542834C (en) | 1972-04-13 |
Family
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