DE1793756B2 - DIURETHANE - Google Patents

DIURETHANE

Info

Publication number
DE1793756B2
DE1793756B2 DE19681793756 DE1793756A DE1793756B2 DE 1793756 B2 DE1793756 B2 DE 1793756B2 DE 19681793756 DE19681793756 DE 19681793756 DE 1793756 A DE1793756 A DE 1793756A DE 1793756 B2 DE1793756 B2 DE 1793756B2
Authority
DE
Germany
Prior art keywords
methyl
phenyl
carbamate
carbamoyloxy
compounds according
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.)
Granted
Application number
DE19681793756
Other languages
German (de)
Other versions
DE1793756C3 (en
DE1793756A1 (en
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 filed Critical
Priority to DE19681793756 priority Critical patent/DE1793756B2/en
Publication of DE1793756A1 publication Critical patent/DE1793756A1/en
Publication of DE1793756B2 publication Critical patent/DE1793756B2/en
Application granted granted Critical
Publication of DE1793756C3 publication Critical patent/DE1793756C3/de
Granted legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verbindung link

Name der VerbindungName of the connection

SchmelzpunkteMelting points

F. = 148—1490CMp = 148-149 0 C.

Methyl-N-(3-(N'-(3'-fluor-Methyl-N- (3- (N '- (3'-fluoro-

phenyl)-carbamoyloxy)-phenyl) carbamoyloxy) -

phenyl)-carbamatphenyl) carbamate

Methyl-N-(3-(N'-n-butyl- F. = 105—1060C N'-(3'-methylphenyl)-Methyl-N- (3- (N'-n-butyl- F. = 105-106 0 C N '- (3'-methylphenyl) -

carbamoyloxy)-phenyl)-carbamoyloxy) -phenyl) -

carbamatcarbamate

Die bisher nicht bekannten Verbindungen können beispielsweise durch Umsetzung von entsprechenden N-Hydroxphenylurethanen mit entsprechenden Isocyanaten oder Carbamidsäurechloriden in an sich bekannter Weise hergestellt werden.The previously unknown compounds can, for example, by reacting appropriate N-Hydroxphenylurethanen with corresponding isocyanates or carbamic acid chlorides per se be produced in a known manner.

Beispielexample

Im Gewächshausversuch wurden die in der Tabelle aufgeführten Pflanzenarten im Nachauflaufverfahren mit den erfindungsgemäßen VerbindungenIn the greenhouse test, the plant species listed in the table were post-emergence with the compounds according to the invention

(1) Methyl-N-(3-(N'-(3'-fluorphenyl)-carbamoyloxy)-phenyl)-carbamat (1) Methyl N- [3- (N '- (3'-fluorophenyl) -carbamoyloxy) -phenyl) -carbamate

(2) Methyl-N-(3-(N'-n-butyl-N'-(3'-methyI-phenyl)-carbamoyloxy)-phenyl)-carbamat (2) Methyl N- [3- (N'-n-butyl-N '- (3'-methyl-phenyl) -carbamoyloxy) -phenyl) -carbamate

sowie den Vergleichsmittelnas well as the comparison means

(3) Methyl-N-(3-(N'-(3'-methylphenyl)-carbamoyloxy)-phenyl)-carbamat (3) methyl N- [3- (N '- (3'-methylphenyl) carbamoyloxy) phenyl) carbamate

4545

(4) Isopropyl-N-(3-chlorphenyl)-carbamat(4) Isopropyl N- (3-chlorophenyl) carbamate

(5) Methyl-N-(3-methylcarbamoyloxyphenyl)-carbamat (5) methyl N- (3-methylcarbamoyloxyphenyl) carbamate

(6) MethyI-N-methyl-N-(3-(N'-me.thyl-N'-(3'-methylphenyl)-carbamoyloxy)-phenyl)-carbamat (6) Methyl-N-methyl-N- (3- (N'-methyl-N '- (3'-methylphenyl) -carbamoyloxy) -phenyl) -carbamate

in einer Aufwandmenge von 3 kg Wirkstoff/ha behandelt. treated at an application rate of 3 kg active ingredient / ha.

Die Mittel wurden als Emulsionen in 500 Liter Wasser je Hektar ausgebracht. Zwei Wochen nach der Behandlung erfolgte die Auswertung durch Bonitur entsprechend einer Bewertungsskala von 0 = »total vernichtet« bis 10 ■-= »nicht geschädigt«.The agents were applied as emulsions in 500 liters of water per hectare. Two weeks after the treatment was evaluated by scoring according to a rating scale of 0 = »total destroyed «up to 10 ■ - =» not damaged «.

Die erhaltenen Befunde zeigen deutlich die wesentlieh bessere Selektivität der erfindungsgemäßen Verbindungen gegenüber den wichtigen Kulturpflanzen Mais, Weizen und Gerste bei ausgezeichneter Unkrautwirkung im Vergleich zu den bekannten MittelnThe results obtained clearly show the essentials better selectivity of the compounds according to the invention with respect to the important crop plants Maize, wheat and barley with excellent weed effects compared to the known agents

3 -^ 43 - ^ 4

TabelleTabel

Verbindungs-Nr. (1) (2) (3) (4) (5) (6) unbe-Connection no. (1) (2) (3) (4) (5) (6) unrelated

handeltacts

Wirkstoff kg/haActive ingredient kg / ha 33 33 33 33 33 33 1010 MaisCorn 1010 77th 33 88th 99 1010 1010 Weizenwheat 1010 1010 22 33 88th 1010 1010 Gerstebarley 1010 1010 22 33 88th 1010 1010 Stellaria mediaStellaria media 00 00 11 11 44th 55 1010 Senecio vulgarisSenecio vulgaris 00 00 00 88th 33 55 1010 Matricaria chamomillaMatricaria chamomilla 00 55 00 55 1010 1010 1010 Lamium amplexicauleLamium amplexicaule 00 11 00 33 44th 44th 1010 Ccntaurea cyanusCcntaurea cyanus 00 11 00 66th 1010 88th 1010 Ipomoea purpureaIpomoea purpurea 11 00 00 22 77th 1010 1010 Polygonum lapathifoliumPolygonum lapathifolium 00 00 00 11 99 1010 1010 Chrysanthemus segetumChrysanthemus segetum 00 00 11 88th 1010 99 0 = total vernichtet0 = totally destroyed 10 = nicht geschädigt10 = not damaged

Claims (2)

Patentansprüche:Patent claims: 1. Methyl-N-(3-(N'-(3'-fluorphenyI)-carbamoyloxy)-phenyl)-carbamat. 1. Methyl N- [3- (N '- (3'-fluorophenyI) -carbamoyloxy) -phenyl) -carbamate. 2. Methyl-N-(3-(N'-n-butyl-N'-(3'-methylphenyl)-carbamoyloxy)-phenyl)-carbamai. 2. Methyl-N- (3- (N'-n-butyl-N '- (3'-methylphenyl) carbamoyloxy) phenyl) carbamai. Die erfindungsgemäßen Verbindungen können allein oder als Mischungen untereinander und/oder mit anderen Herbiziden und/oder sonstigen Stoffen, z. B. Düngemitteln, angewandt werden.The compounds according to the invention can be used alone or as mixtures with one another and / or with other herbicides and / or other substances, e.g. B. fertilizers are applied. Die Anwendung der ernndungsgemaßen Vermndungen erfolgt zweckmäßig in einer für eine Unkrautbekämpfung üblichen Weise in Form von Zubereitungen, wie z. B. Pulvern, Streumittel, Granulaten, Lösungen- Emulsionen oder Suspensionen, unter Zusatz von flüssigen und/oder festen Trägerstoffen bzw Verdünnungsmitteln und gegebenenfalls von Netz-, Haft-, Emulgier- und/oder Dispergierhiifs-The application of the appointments according to the invention is expediently carried out in a manner customary for weed control in the form of preparations, such as. B. powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and optionally wetting agents, adhesives, emulsifying agents and / or dispersing agents mitteln. .average. . Die Herstellung der verschiedenen Zubereitungsformen erfolgt in ansich bekannter Art und Weise, z. B. durch Mahl- bzw. Mischverfahren.The production of the various forms of preparation takes place in a manner known per se, z. B. by grinding or mixing processes. Zur selektiven Unkrautbekämpfung haben sich zum Teil schon Aufwandmengen von etwa 0,3 kg Wirksubstanz/ha an als ausreichend erwiesen.For selective weed control, in some cases, application rates of around 0.3 kg of active substance / ha have been found proved to be sufficient. Die herbizide Wirkung der erfindungsgemäßen Verbindungen geht aus dem folgenden Versuchsbeispiel hervor.The herbicidal action of the compounds according to the invention is shown in the following experimental example emerged. Die herbizide Wirkung von Phenylcarbamaten, z. B. Isopropyl-N-P-chlorphenyO-carbamat (DT-PS 8 33 274), Methyl-N-O-CN'-P'-methylphenyO-carbamoyloxy)-phenyl)-carbamat (BE-PS 6 79 283,700942, 7 03 644 und 7 03 646), Methyl-N-(3-methylcarbamoyloxv-phenyl)-carbamat (BE-PS 6 89 440) und Methyl-N-methyl-N-P-tN'-methyl-N'-O'-methylphenyO-carbamoyloxy)-phenyl)-carbamat (BE-PS 7 03 646) ist bereits bekanrit. Diese Mittel zeigen jedoch eine unbefriedigende Selektivität gegenüber wichtigen Kulturpflanzen, wie Mais, Weizen und Gerste.The herbicidal effects of phenyl carbamates, e.g. B. Isopropyl-N-P-chlorophenyO-carbamate (DT-PS 8 33 274), methyl-N-O-CN'-P'-methylphenyO-carbamoyloxy) -phenyl) -carbamate (BE-PS 6 79 283,700942, 7 03 644 and 7 03 646), methyl N- (3-methylcarbamoyloxv-phenyl) -carbamate (BE-PS 6 89 440) and methyl-N-methyl-N-P-tN'-methyl-N'-O'-methylphenyO-carbamoyloxy) -phenyl) -carbamate (BE-PS 7 03 646) is already known. However, these means show an unsatisfactory one Selectivity towards important crops such as maize, wheat and barley. Es wurde nun gefunden, daß das Methyl-N-(3-(N'-(3'-fluorphenyl)-carbamoyloxy)-phenyl)-carbamat und das MethyI-N-(3-(N'-n-butyl-N'-(3'-methyIphenyl)-carbamoyloxy)-phenyl)-carbamat eine wesentlich bessere Selektivität gegenüber diesen Kulturpflanzen als die bekannten Stoffe sowie eine ausgezeichnete Unkrautwirkung aufweisen.It has now been found that the methyl N- (3- (N '- (3'-fluorophenyl) -carbamoyloxy) -phenyl) -carbamate and methyl N- (3- (N'-n-butyl-N '- (3'-methylphenyl) carbamoyloxy) phenyl) carbamate a much better selectivity towards these crops than the known substances and an excellent weed effect exhibit. Die Verbindungen gemäß der Erfindung haben die folgenden Schmelzpunkte:The compounds according to the invention have the following melting points:
DE19681793756 1968-06-20 1968-06-20 DIURETHANE Granted DE1793756B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19681793756 DE1793756B2 (en) 1968-06-20 1968-06-20 DIURETHANE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19681793756 DE1793756B2 (en) 1968-06-20 1968-06-20 DIURETHANE

Publications (3)

Publication Number Publication Date
DE1793756A1 DE1793756A1 (en) 1973-05-24
DE1793756B2 true DE1793756B2 (en) 1976-12-16
DE1793756C3 DE1793756C3 (en) 1978-05-18

Family

ID=5707796

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19681793756 Granted DE1793756B2 (en) 1968-06-20 1968-06-20 DIURETHANE

Country Status (1)

Country Link
DE (1) DE1793756B2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2413933A1 (en) * 1974-03-20 1975-09-25 Schering Ag DIURETHANE WITH SELECTIVE HERBICIDAL EFFECT

Also Published As

Publication number Publication date
DE1793756C3 (en) 1978-05-18
DE1793756A1 (en) 1973-05-24

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Legal Events

Date Code Title Description
C3 Grant after two publication steps (3rd publication)