DE1793756C3 - - Google Patents

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Publication number
DE1793756C3
DE1793756C3 DE19681793756 DE1793756A DE1793756C3 DE 1793756 C3 DE1793756 C3 DE 1793756C3 DE 19681793756 DE19681793756 DE 19681793756 DE 1793756 A DE1793756 A DE 1793756A DE 1793756 C3 DE1793756 C3 DE 1793756C3
Authority
DE
Germany
Prior art keywords
methyl
carbamate
phenyl
carbamoyloxy
methylphenyl
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
Application number
DE19681793756
Other languages
German (de)
Other versions
DE1793756A1 (en
DE1793756B2 (en
Inventor
Gerhard Dr. 1000 Berlin Boroschewski
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.)
Bayer Pharma AG
Original Assignee
Schering AG
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 Schering AG filed Critical Schering AG
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

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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

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  • 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

Verbin dungConnect manure

Name der VerbindungName of the connection

Melhyl-N-(3-(N'-hulyl-Melhyl-N- (3- (N'-hulyl-

N'-(3'-mcth>lphenyl)-carh-N '- (3'-mcth> lphenyl) -carh-

anu>yloxy)-phcnyl)-carbanialanu> yloxy) -phynyl) -carbanial

SchmelzpunktMelting point

F. 105 106 CF. 105 106 C

Die bisher nicht bekannte Verbindung kann beispielsweise durch Umsetzung von entsprechenden N-Hydroxyphcnylurcthancii mit entsprechenden Isocyanaten oder Caibaniidsäurechloriden in au sich bekannter Weise hergestellt werden.The previously unknown compound can, for example, by implementing appropriate N-Hydroxyphcnylurcthancii with corresponding isocyanates or caibaniidic acid chlorides per se be produced in a known manner.

I )ie eiTniduugsgenuiße Verbindung kann allein oder .ils Mischung mit anderen Herbiziden und/oderI) The enjoyable connection can be used alone or .ils Mixture with other herbicides and / or

TabelleTabel

sonstigen Stoffen, zum Beispiel Düngemitteln, angewandt werden.other substances, e.g. fertilizers, applied will.

Die Anwendung der erfindungsgemäßen Verbindung erfolgt zweckmäßig in einer für eine Unkraut-Ί bekänipfung üblichen Weise in Form von Zubereitungen, wie zum Beispiel Pulvern, Streumittel. Granulaten, Lösungen, Emulsionen oder Suspensionen, unter Zusatz von flüssigen und/oder festen Trägersloffen beziehungsweise Verdünnungsmitteln in und gegebenenfalls von Netz-, Haft-, Emulgier- und/ oder Dispergierhilfsmitleln.The compound according to the invention is expediently used in a weed Ί the usual way in the form of preparations, such as powders, grit. Granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents in and, if necessary, of wetting, adhesive, emulsifying and / or dispersing aids.

Die Herstellung der verschiedenen Zuberei'ungsformen erfolgt in an sich bekannter Art und Weise, zum Beispiel durch Mahl- beziehungsweise Mischi" > verfahren.The production of the various forms of preparation takes place in a manner known per se, for example by grinding or mixing " > proceed.

Zur selektiven Unkraulbekämpfung haben sich zum Teil schon Aufwandmengen von etwa 0,3 kg Wirksubstunz/hu an als ausreichend erwiesen.For selective weed control, in some cases, application rates of around 0.3 kg of active substance / hu have been found proved to be sufficient.

Die herbizide Wirkung der erlindungsgemäßen Ver- -'» bindung geht aus den folgenden Versuchsbeispiden hervor.The herbicidal effect of the compound according to the invention is based on the following experimental examples emerged.

Beispiel IExample I.

_'"> Im Gewächshausversueh wurden die in der Tabelle aufgerührten Pllanzenarten im Nachauflaufverfahren mit der erfindungsgemäßen Verbindung_ '"> In the greenhouse experiment the in the table listed plant species in the post-emergence process with the compound according to the invention

(1) Melhyl-N-(3-(N'-n-bulyl-N'-(3'-meth\l-phenyl)-earbanioyloxy)-phenyl)-carbamat (1) Methyl-N- (3- (N'-n-bulyl-N '- (3'-meth \ l-phenyl) -earbanioyloxy) -phenyl) -carbamate

sowie den Vergleichsmilldnas well as the comparative mill

(2) Melhyl-N-(3-(N'-(3'-melhylphenyl)-carbamoylo\y)-phenyl)-carbamat (2) Methyl-N- (3- (N '- (3'-methylphenyl) -carbamoylo \ y) -phenyl) -carbamate

(3) lsopropyl-N-(3-chlorphcnyl)-carbamat(3) Isopropyl N- (3-chlorophynyl) carbamate

!l (4) Melh\l-N-(3-melhylcarbamoylo\yphenyl|- ! l (4) Melh \ lN- (3-methylcarbamoylo \ yphenyl | -

carbamat
(5) Methyl-N-methyl-N-(3-(N'-melh)l-carbamate
(5) methyl-N-methyl-N- (3- (N'-melh) l-

N-(.V-niethylphenyl)-carbanioylo\y |-phenyl)-carbamat N - (. V-niethylphenyl) -carbanioylo (y | -phenyl) -carbamate

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

Die Mittel wurden als Emulsionen in 500 liter Wasser je Hektar ausgebracht. Zwei Wochen nachThe agents were applied as emulsions in 500 liters of water per hectare. Two weeks after

Γι der Behandlung erfolgte die Auswertung durch Boiiiturentsprecheiul einer Bewertungsskiila von I) »total vernichtet« bis IO = »nicht geschädigt«.After the treatment, the evaluation was carried out by Boiiiturentsprecheiul an evaluation skiila from I) "totally destroyed" to IO = "not damaged".

Die erhaltenen Befunde /eigen deutlich die wesentlich bessere Selektivität der eriiiuiiingsgeniiißeu Ver-The results obtained clearly show the significantly better selectivity of the

i(i bindung gegenüber den wichtigen Kultiupllaii/en Mais, Weizen und Geiste bei ausgezeichneter Unkiaulwiikuim im Vergleich /u den bekaiinlen Mitteln.i (i bond to the important cultural sites Corn, wheat and spirits with excellent Unkiaulwiikuim in comparison to the known means.

Verbindungc Nr.Connection no. (I)(I) (2)(2) (H(H . Hl. St. (51(51 iinbchandcltiinbchandclt Wiikstoff kghaWiikstoff kgha }} \\ ii .1.1 33 MaisCorn 11 II. SS. ')') IOIO 1010 Weizenwheat IOIO )) ii SS. IOIO 1010 (iei'sle(iei'sle lolo >> \\ SS. 1010 1010 Stell,iiKi MiL(Ii.ιStell, iiKi MiL (Ii.ι (I(I. II. II. II. SS. IIIIII Scnecio vulgarisScnecio vulgaris 00 I)I) SS. \\ IUIU Mali icai u lIi.iiiiiimiiII.iMali icai u lIi.iiiiiimiiII.i IlIl ■>■> ItIItI 1010 IIIIII I .1 in ι lim .mij)k-\jc;i nieI .1 in ι lim .mij) k- \ jc; i never II. IlIl \\ II. II. IIIIII ( eilt.line.ι ι vaniis(eilt.line.ι ι vaniis II. IlIl (>(> InIn ι nι n

3
Fortsetzung 3
continuation (D(D 17 93 75617 93 756 (5)(5) 44th un behandeltun treated Vcrbindungs-Nr.Connection No. 0
0
00
0
0 (2) (3) (4)(2) (3) (4) IO
IO
υ IO
IO
υ K)
K)
10K)
K)
10 Ipomoea purpurea
Polygonum lapathi-
folium
C'hrysanthemus
segetum
0 = total vernichtet.
10 = nicht geschädigt. Ipomoea purpurea
Polygonum lapathi-
folium
C'hrysanthemus
segetum
0 = totally destroyed.
10 = not damaged. 0 2 7
0 I 4
1 8 100 2 7
0 I 4
1 8 10

Beispiel 2Example 2

Im Gewächshausversueh wurden dl·", in der Tabelle aufgeführten Pllan/enarten im Nachaiiflaufverfahreii mit der erfindungsgemäßen VerbindungIn Gewächshausversueh dl · "were in the table listed Plélan / enarten in Nachaiiflaufverfahreii with inventive compound

(I) Methyl-N-(3-(N'-n-bulyI-N'-(.V-meth)lphen>l)-carbamoyloxy)-phenyl)-carbamat (I) methyl N- [3- (N'-n-bulyI-N '- (. V-meth) lphen> l) -carbamoyloxy) -phenyl) -carbamate

sowie dem Vergleichsmittelas well as the comparison means

(6) \lelhyl-N-(3-<N'-(3-lluorphen>l)-carbamo>loxy)-phen >l)-carbamat(6) \ lethyl-N- (3- <N '- (3-fluorophen> l) -carbamo> loxy) -phen > l) carbamate

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

Die Mittel wurden als Emulsionen in 500 Liter Wasser je Hektar ausgebracht. Zwei Wochen nach der Uehandlung erfolgte die Auswertung durch Bonitur entsprechend einer Bewerlungsskala 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 The evaluation was carried out by means of a rating according to a rating scale from 0 - "totally destroyed" to 10 = "not damaged".

Die erhaltenen Befunde /eigen deutlich die wesentlich bessere Selektivität der erfind ungsgenüilten Verbindung gegenüber Baumwolle bei hervorragender herbi/ider Wirkung gegen Amarantus r. und andere Unkräuter im Veruleich/ti der bekannten VerbindungThe findings obtained clearly show the significantly better selectivity of the compound in accordance with the invention compared to cotton with excellent herbicidal action against Amarantus r. and other Weeds in the Veruleich / ti the known connection

π Tabelleπ table (D(D (6)(6) UnbehandeltUntreated Verbindungs-Nr.Connection no. 33 33 -'<> Wirkstoff kg/ha- '<> active ingredient kg / ha IOIO 00 1010 Baumwollecotton 00 00 1010 Stellaria mediaStellaria media 00 00 IOIO Senecio vulgarisSenecio vulgaris II. 00 IOIO ->-, La mi um -> -, La mi around amplexicauleamplexicaule 11 00 IOIO C'entaurea cyanusCentaurea cyanus 00 II. IOIO Ipomoea purpureaIpomoea purpurea 00 00 K)K) PolygonumPolygonum lapathifoliumlapathifolium 00 00 1010 ChrysanthemumChrysanthemum segetumsegetum 00 SS. M)M) AmarantusAmarantus li retrollexusli retrollexus 0 = total vernichtet.0 = totally destroyed. 10 = nicht geschädigt.10 = not damaged.

Claims (1)

Patentanspruch:Claim: Methyl-N-(3-(N'-n-bulyl-N'-(3-melhylphenyl)-carbamovlox>)-phenyl)-carbamal. Methyl-N- (3- (N'-n-bulyl-N '- (3-methylphenyl) -carbamovlox>) -phenyl) -carbamal. Die herbizide Wirkung von Phenylcarbamalen. zum Beispiel Isopropyl-N-p-chlorphenyll-carbamat (DE-PS8 33 274),Methyl-N-(3-(N'-(3'-melhylphenyI)-carbamoyloxy)-phenyl)-carbamat (BE-PS679283, 700942, 7 03 644 und 7 03 646), Methyl - N - (3 - melhylcarbamoyloxy-phenyD-carbamat (BE-PS 6 89 440) und Methyl - N - methyl - N - (3 - (N' - methyl - N' - (3' - melhylphenyl)-carbainoyloxy)-phenyl)-earbamal (BE-PS-7 03 646) ist bereits bekannt. Diese Mittel zeigen jedoch eine unbefriedigende Selektivität gegenüber wichtigen Kulturpflanzen, wie Mais, Weizen und Gerste.The herbicidal effects of phenylcarbamals. for example isopropyl-N-p-chlorophenyl-carbamate (DE-PS8 33 274), methyl N- [3- (N '- (3'-methylphenyI) -carbamoyloxy) -phenyl) -carbamate (BE-PS 679283, 700942, 7 03 644 and 7 03 646), methyl - N - (3 - methylcarbamoyloxy-phenyD-carbamate (BE-PS 6 89 440) and methyl - N - methyl - N - (3 - (N '- methyl - N' - (3 '- methylphenyl) -carbainoyloxy) -phenyl) -earbamal (BE-PS-7 03 646) is already known. However, these agents show an unsatisfactory selectivity towards important crops such as corn, wheat and barley. In der BE-PS 7 (M) 942 wird unter anderem auch das Methyl- N-(3-(N'-(3'-IUiorphenyl)-cai"hanioyloxy)-phenyll-carbama! beschrieben, welches jedoch nicht in Baumwolle verwendet werden kann.In BE-PS 7 (M) 942, among other things, the methyl-N- (3- (N '- (3'-IUiorphenyl) -cai "hanioyloxy) -phenyll-carbama! which, however, cannot be used in cotton. Es wurde nun gefunden, daß das Melhyl-N-(3-N-n - butyl - N' - (3' - methylphcnyl) - carbamoyloxy)-phenyll-carbamat eine wesentlich bessere Selektivität gegenüber diesen Kulturpflanzen als die bekannten Stoffe sowie eine ausgezeichnete Unkrauiwirkimg aufweist. It has now been found that methyl-N- (3-N-n-butyl-N '- (3' - methylphynyl) - carbamoyloxy) phenyl carbamate a much better selectivity towards these crops than the known ones Substances as well as an excellent weed effect. Die Verbindung gemäß der Erfindung hat den folgenden Schmelzpunkt:The compound according to the invention has the following melting point:
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 DE1793756B2 (en) 1976-12-16
DE1793756C3 true 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
DE1793756A1 (en) 1973-05-24
DE1793756B2 (en) 1976-12-16

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Legal Events

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C3 Grant after two publication steps (3rd publication)