DE1018261B - Agent for combating unwanted vegetation - Google Patents

Agent for combating unwanted vegetation

Info

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
Application number
DEB40724A
Other languages
German (de)
Inventor
Dr Hermann Windel
Dr Ludwig Weschky
Dr Adolf Fischer
Dr Herbert Stummeyer
Dr Carl Pfaff
Dr Gustav Steinbrunn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DEB40724A priority Critical patent/DE1018261B/en
Publication of DE1018261B publication Critical patent/DE1018261B/en
Pending legal-status Critical Current

Links

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)

PATENTANSPRÜCHE: 1. Mittel zur Bekämpfung - unerwünschten Pflanzenwachstums, gekennzeichnet durch einen Gehalt an Hydantoinderivaten der Formel in der Y Alkyl, Oxyalkyl oder Halogen, n die Zahlen 1, 2 oder 3, wobei im Falle von n = 3 die beiden Substituenten gleich oder verschieden sein können, und R Wasserstoff, den Methylrest oder den Carboxymethylrest bedeuten. PATENT CLAIMS: 1. Means for controlling - unwanted plant growth, characterized by a content of hydantoin derivatives of the formula 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 radical or the carboxymethyl radical. 2. Mittel gemäß Anspruch 1, gekennzeichnet durch einen Gehalt an 1-Methyl-3-(p-chlorphenyl)-hydantoin. In Betracht gezogene Druckschriften: Nachrichtenblatt für den deutschen Pflanzenschutz, 6. Jahrgang, 1952, Heft 10, S. 187 bis 196.2. Agent according to claim 1, characterized by a content of 1-methyl-3- (p-chlorophenyl) hydantoin. Publications considered: News sheet for German plant protection, 6th year, 1952, issue 10, pp. 187 to 196.
DEB40724A 1956-06-20 1956-06-20 Agent for combating unwanted vegetation Pending DE1018261B (en)

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 (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP0069855A2 (en) * 1981-05-29 1983-01-19 Sumitomo Chemical Company, Limited N-(2-fluoro-4-halo-5-substituted phenyl)hydantoins, and their production and use
WO2007047146A2 (en) * 2005-10-11 2007-04-26 Intermune, Inc. Inhibitors of viral replication

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP0069855A2 (en) * 1981-05-29 1983-01-19 Sumitomo Chemical Company, Limited N-(2-fluoro-4-halo-5-substituted phenyl)hydantoins, and their production and use
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
WO2007047146A2 (en) * 2005-10-11 2007-04-26 Intermune, Inc. Inhibitors of viral replication
WO2007047146A3 (en) * 2005-10-11 2007-11-01 Intermune Inc Inhibitors of viral replication

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