DE1018261B - Agent for combating unwanted vegetation - Google Patents
Agent for combating unwanted vegetationInfo
- Publication number
- DE1018261B DE1018261B DEB40724A DEB0040724A DE1018261B DE 1018261 B DE1018261 B DE 1018261B DE B40724 A DEB40724 A DE B40724A DE B0040724 A DEB0040724 A DE B0040724A DE 1018261 B DE1018261 B DE 1018261B
- Authority
- DE
- Germany
- Prior art keywords
- hydantoin
- methyl
- agent
- unwanted vegetation
- chlorophenyl
- 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
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 6
- 229940091173 hydantoin Drugs 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- -1 carboxymethyl radical Chemical class 0.000 claims description 4
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 claims description 3
- 150000001469 hydantoins Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 235000006463 Brassica alba Nutrition 0.000 description 2
- 244000140786 Brassica hirta Species 0.000 description 2
- 240000005702 Galium aparine Species 0.000 description 2
- 235000014820 Galium aparine Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- YLKKRCYFGKGCKZ-UHFFFAOYSA-N 1-methyl-3-phenylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1C1=CC=CC=C1 YLKKRCYFGKGCKZ-UHFFFAOYSA-N 0.000 description 1
- XFWXNZDKOJBRKF-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1C1=CC=C(Cl)C(Cl)=C1 XFWXNZDKOJBRKF-UHFFFAOYSA-N 0.000 description 1
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000007754 Achillea millefolium Nutrition 0.000 description 1
- 244000294263 Arctium minus Species 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 241000380130 Ehrharta erecta Species 0.000 description 1
- 235000003805 Musa ABB Group Nutrition 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000015266 Plantago major Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Mittel zur Bekämpfung unerwünschten Pflanzenwuchses Für die Bekämpfung unerwünschten Pflanzenwuchses verwendet man seit langem Chlorate. Diese besitzen eine ausgezeichnete pflanzenabtötende Wirksamkeit, haben aber den Nachteil, daß sie infolge ihrer Giftigkeit und Ätzwirkung schwer zu handhaben sind, die behandelten Pflanzen leicht entflammbar machen und Geräte aus Eisen angreifen.Means for combating unwanted vegetation. For combating Chlorates have long been used for undesired vegetation. Own this an excellent herbicidal activity, but have the disadvantage that they are difficult to handle due to their toxicity and corrosivity, the treated Making plants easily flammable and attacking iron equipment.
Es wurde gefunden, daß von diesen Nachteilen frei sind Hydantoinderivate der Formel in der Y Alkyl, Oxyalkyl oder Halogen, n die Zahlen 1, 2 oder 3, wobei im Falle von n = 3 die beiden Substitutenten gleich oder verschieden sein können, und R Wasserstoff, den Methyl- oder Carboxymethylrest bedeuten. Beispielsweise sind 1-Methy 1-3-(pchlorphenyl)-hydantoin, 1-Methyl-3-(3, 4-dichlorphenyl)-hydantoin., 3-(p-Chlorphenyl)-hydantoin, 1- Methyl - 3 -phenyl -hydantoin, 1- Methyl-3-(3-chlor-4-methyl-phenyl)-hydantoin und 1-Carboxymethyl-3-(p-chlorphenyl)-hydantoin für die genannten Zwecke gut geeignet.It has been found that hydantoin derivatives of the formula are free from these disadvantages in which Y is alkyl, oxyalkyl or halogen, n is the numbers 1, 2 or 3, where in the case of n = 3 the two substituents can be identical or different, and R is hydrogen, the methyl or carboxymethyl radical. For example, 1-methy 1-3- (pchlorphenyl) hydantoin, 1-methyl-3- (3, 4-dichlorophenyl) hydantoin., 3- (p-chlorophenyl) hydantoin, 1- methyl - 3 -phenyl - hydantoin, 1-methyl-3- (3-chloro-4-methyl-phenyl) -hydantoin and 1-carboxymethyl-3- (p-chlorophenyl) -hydantoin are well suited for the purposes mentioned.
Diese Hydantoinderivate können durch Umsetzung der Isocyanate oder Carbaminsäurechloride mit einem aromatischen primären Amin oder mit einer primären oder sekundären aliphatischen Aminocarbonsäure hergestellt werden.These hydantoin derivatives can by reacting the isocyanates or Carbamic acid chlorides with an aromatic primary amine or with a primary or secondary aliphatic aminocarboxylic acid.
Die Anwendung kann als Lösung in einem organischen Lösungsmittel, als Suspension in Wasser oder einem anderen Nichtlösungsmittel unter Verwendung eines Dispergiermittels oder in fester Form zusammen mit einem feinteiligen Trägerstoff oder mit Düngemitteln erfolgen. Die Wirkung kann durch Zusatz eines Haftmittels verbessert werden.The application can be as a solution in an organic solvent, as a suspension in water or another nonsolvent using a dispersant or in solid form together with a finely divided carrier or with fertilizers. The effect can be achieved by adding an adhesive be improved.
Beispiel 1 Man besprüht Erde mit einer wäßrigen Lösung von 1-Methyl-3-(p-chlorphenyl)-hydantoin, die unter Zusatz eines Dispergier- oder Emulgiermittels hergestellt ist, entsprechend einer Wirkstoffmenge von 1 bis 5 kg je Hektar. In einen so vorbereiteten Boden eingesäte Samen von Sinapis alba (Senf), Panicum sanguinale (Bluthirse) und Galium aparine (Klettenlabkraut) entwickeln zwar zunächst Keimlinge. Die jungen Pflänzchen gehen aber früher oder später ein und werden vollkommen vernichtet. Beispiel 2 1-Methyl-3-(p-chlorphenyl)-hydantoin wird in Mengen von 5 und 10 kg je Hektar in 10000 1 Wasser bei folgenden Pflanzen im Gewächshaus angewendet: Avena fatua, Sinapis alba, Galium aparine. Nach 3 bis 4 Tagen beginnen die Pflanzen an den Blattspitzen zu welken und sind nach etwa 14 Tagen, besonders bei der Menge von 10 kg, vollkommen abgestorben.Example 1 Earth is sprayed with an aqueous solution of 1-methyl-3- (p-chlorophenyl) hydantoin, which is produced with the addition of a dispersing or emulsifying agent, accordingly an amount of active ingredient of 1 to 5 kg per hectare. Sown in such a prepared soil Sinapis alba (mustard), Panicum sanguinale (blood millet) and Galium aparine seeds (Burdock weed) initially develop seedlings. The young plants go but sooner or later one and will be completely destroyed. Example 2 1-methyl-3- (p-chlorophenyl) hydantoin is used in quantities of 5 and 10 kg per hectare in 10000 1 of water for the following plants used in the greenhouse: Avena fatua, Sinapis alba, Galium aparine. After 3 to 4 days the plants begin to wither at the leaf tips and are after about 14 Days, especially with the amount of 10 kg, completely dead.
Beispiel 3 Auf Ödland werden perennierende Gräser, Löwenzahn, Wegerich, Schafgarbe und Klee mit 1-Methyl-3-(p-Chlorphenyl)-hydantoin in einer Menge von 30 kg in 1000 1 Wasser je Hektar besprüht. Die Pflanzen sind nach 14 bis 20 Tagen ohne Ausnahme vernichtet. Auch nach etwa 3 Monaten wird kein neuer Pflanzenwuchs beobachtet.Example 3 Perennial grasses, dandelions, plantain, Yarrow and clover with 1-methyl-3- (p-chlorophenyl) hydantoin in an amount of 30 kg sprayed in 1000 liters of water per hectare. The plants are after 14 to 20 days destroyed without exception. Even after about 3 months there will be no new vegetation observed.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB40724A DE1018261B (en) | 1956-06-20 | 1956-06-20 | Agent for combating unwanted vegetation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB40724A DE1018261B (en) | 1956-06-20 | 1956-06-20 | Agent for combating unwanted vegetation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1018261B true DE1018261B (en) | 1957-10-24 |
Family
ID=6966168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB40724A Pending DE1018261B (en) | 1956-06-20 | 1956-06-20 | Agent for combating unwanted vegetation |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1018261B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1039302B (en) | 1957-06-21 | 1958-09-18 | Bayer Ag | Preparations for influencing plant growth |
| US3443925A (en) * | 1964-12-16 | 1969-05-13 | United States Borax Chem | Method of controlling weed growth |
| FR2024141A1 (en) * | 1968-11-25 | 1970-08-28 | Sumitomo Chemical Co | |
| US3755350A (en) * | 1970-10-06 | 1973-08-28 | Rhone Poulenc Sa | Substituted 3-phenyl hydantoins useful as fungicides |
| EP0069855A3 (en) * | 1981-05-29 | 1983-03-30 | Sumitomo Chemical Company, Limited | N-(2-fluoro-4-halo-5-substituted phenyl)hydantoins, and their production and use |
| WO2007047146A3 (en) * | 2005-10-11 | 2007-11-01 | Intermune Inc | Inhibitors of viral replication |
-
1956
- 1956-06-20 DE DEB40724A patent/DE1018261B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1039302B (en) | 1957-06-21 | 1958-09-18 | Bayer Ag | Preparations for influencing plant growth |
| US3443925A (en) * | 1964-12-16 | 1969-05-13 | United States Borax Chem | Method of controlling weed growth |
| FR2024141A1 (en) * | 1968-11-25 | 1970-08-28 | Sumitomo Chemical Co | |
| US3668217A (en) * | 1968-11-25 | 1972-06-06 | Sumitomo Chemical Co | 3-(3{40 ,5{40 -dihalogenophenyl)imidazolidine-2,4-dione derivatives |
| US3755350A (en) * | 1970-10-06 | 1973-08-28 | Rhone Poulenc Sa | Substituted 3-phenyl hydantoins useful as fungicides |
| EP0069855A3 (en) * | 1981-05-29 | 1983-03-30 | Sumitomo Chemical Company, Limited | N-(2-fluoro-4-halo-5-substituted phenyl)hydantoins, and their production and use |
| WO2007047146A3 (en) * | 2005-10-11 | 2007-11-01 | Intermune Inc | Inhibitors of viral replication |
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