DE1793751C3 - Diurethanes and herbicidal compositions containing them - Google Patents
Diurethanes and herbicidal compositions containing themInfo
- Publication number
- DE1793751C3 DE1793751C3 DE19661793751 DE1793751A DE1793751C3 DE 1793751 C3 DE1793751 C3 DE 1793751C3 DE 19661793751 DE19661793751 DE 19661793751 DE 1793751 A DE1793751 A DE 1793751A DE 1793751 C3 DE1793751 C3 DE 1793751C3
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- carbamate
- carbamoyloxy
- diurethanes
- compositions containing
- 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
- 230000002363 herbicidal Effects 0.000 title description 6
- 239000000203 mixture Substances 0.000 title description 3
- 150000001875 compounds Chemical group 0.000 claims description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 3
- 239000004009 herbicide Substances 0.000 claims description 2
- -1 (O-carbamoyloxy) phenyl Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 9
- VXPLXMJHHKHSOA-UHFFFAOYSA-N Propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 240000000772 Brassica cretica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 235000007639 Anthemis cotula Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N Chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 240000006223 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive Effects 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N carbamoyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000001544 chamomile Nutrition 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DXDDOFMELPWPMI-UHFFFAOYSA-N ethyl N-hydroxy-N-phenylcarbamate Chemical class CCOC(=O)N(O)C1=CC=CC=C1 DXDDOFMELPWPMI-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Description
Die Erfindung betrifft neue Diurethane sowie herbizide Mittel, enthaltend diese Verbindungen als Wirkstoffe. The invention relates to new diurethanes and herbicidal compositions containing these compounds as active ingredients.
Die herbizide Wirkung von Phenylcarbamaten, z. B. Isopropyl-N-phenylcarbamat und Isopropyl-N-(3-chlorphenyl)-carbamat, ist bereits bekannt (DT-PS 8 33 274). Diese Mittel zeigen jedoch eine ungenügende Breitenwirkung, da wesentliche Ackerunkräuter, wie Kreuzkraut, Kamille und Franzosenkraut, nicht oder nur unbefriedigend bekämpft werden.The herbicidal effects of phenyl carbamates, e.g. B. Isopropyl N-phenyl carbamate and isopropyl N- (3-chlorophenyl) carbamate, is already known (DT-PS 8 33 274). However, these means show an insufficient one Widespread effect, since essential field weeds such as ragwort, chamomile and French herb, not or can only be fought unsatisfactorily.
Es wurde nun gefunden, daß die folgenden Diurethane, dasIt has now been found that the following diurethanes, the
Verbin- Name der VerbindungConnection name of the connection
SchmelzpunkteMelting points
Äthyl-N-(3-(N'-(3',4'-di-Ethyl-N- (3- (N '- (3', 4'-di-
chlorphenyl)-carbamoyl-chlorophenyl) carbamoyl
oxy)-phenyl)-carbamatoxy) phenyl) carbamate
Methyl-N-(3-(N'-(3',4'-di-Methyl-N- (3- (N '- (3', 4'-di-
chlorphenyO-carbamoyl-chlorphenyO-carbamoyl-
oxy)-phenyl)-carbamatoxy) phenyl) carbamate
F. 154—155° C154-155 ° C
F. 188—190° C188-190 ° C
6o6o
65 Methyl-N-(3-(N'-(3'-chlor-65 methyl-N- (3- (N '- (3'-chloro-
4'-methylphenyl)-carb-4'-methylphenyl) -carb-
amoyloxy)-phenyl)-carb-amoyloxy) -phenyl) -carb-
amatamat
Athyl-N-(3-(N'-(3'-chlor-Ethyl-N- (3- (N '- (3'-chloro-
4'-methylphenyl)-carb-4'-methylphenyl) -carb-
amoyloxy)-phenyl)-carb-amoyloxy) -phenyl) -carb-
amatamat
F. 167—168°C167-168 ° C
F.150—I51°C150-151 ° C
Diese bisher nicht bekannten Verbindungen können beispielsweise nach folgenden Verfahren in an sich bekannter Weise hergestellt werden:These hitherto unknown compounds can, for example, in per se by the following process can be produced in a known way:
durch Umsetzung von N-Hydroxyphenylurethanen der allgemeinen Formelby reacting N-hydroxyphenyl urethanes of the general formula
Äthyl - N - (3 - (N' - (3',4' - dichlorphenyl) - carbamoyloxy)-phenyl)-carbamat, dasEthyl - N - (3 - (N '- (3', 4 '- dichlorophenyl) - carbamoyloxy) -phenyl) -carbamate, that
Methyl - N - (3 - N' - (3',4' - dichlorphenyl) - carbamoyloxy)-phenyl)-carbamat, dasMethyl - N - (3 - N '- (3', 4 '- dichlorophenyl) - carbamoyloxy) phenyl) carbamate, that
Methyl - N - (3 - (N' - (3' - chlor - 4' - methylphenyl)-carbamoyloxy)-phenyl)-carbamat und dasMethyl - N - (3 - (N '- (3' - chloro - 4 '- methylphenyl) carbamoyloxy) phenyl) carbamate and the
Äthyl - N - (3 - (N' - (3' - chlor - 4' - methylphenyl)-carbamoyloxy)-phenyl)-carbamat Ethyl - N - (3 - (N '- (3' - chloro - 4 '- methylphenyl) carbamoyloxy) phenyl) carbamate
breit wirksam gegen eine Vielzahl von Unkräutern, insbesondere auch dikotyle Pflanzenarten, sind.are broadly effective against a large number of weeds, in particular also dicotyledonous plant species.
Diese Wirkung erstreckt sich sowohl auf die Anwendung im Vorauflauf- als auch im Nachauflaufverfahren und erlaubt daher die Verwendung der Mittel, welche diese Verbindungen enthalten, je nach der gewünschten Anwendungsart. Ein weiterer Vorteil ist die Wirksamkeit be> der Kontaktbehandlung über die Blätter etablierter Unkräuter.This effect extends to both pre-emergence and post-emergence applications and therefore allows the agents containing these compounds to be used as desired Type of application. Another advantage is the effectiveness of contact treatment over the Leaves of established weeds.
Es hat sich außerdem gezeigt, daß einige der Verbindungen eine selektive herbizide Wirkung besitzen und beispielsweise zur Unkrautbekämpfung in Rübenkulturen eingesetzt werden können.It has also been found that some of the compounds have selective herbicidal activity and can be used, for example, for weed control in beet crops.
Die Verbindungen gemäß der Erfindung haben die folgenden Schmelzpunkte:The compounds according to the invention have the following melting points:
mitWith
a) Isocyanaten der allgemeinen Formela) Isocyanates of the general formula
R1-N=C=OR 1 -N = C = O
in Gegenwart eines Katalysators, zweckmäßig einer organischen Base, bevorzugt Triäthylamin, oderin the presence of a catalyst, advantageously an organic base, preferably triethylamine, or
b) Carbamidsäurechloriden der allgemeinen Formelb) Carbamic acid chlorides of the general formula
R,R,
O
N—C—ClO
N — C — Cl
in Gegenwart eines Säureakzeptors, zweckmäßig einer anorganischen oder organischen Base, bevorzugt Pyridin, wobei R3 Methyl oder Äthyl, R2 Wasserstoff und R, 3,4-Dichlorphenyl oder S-ChloM-methylphenyl bedeutet.in the presence of an acid acceptor, expediently an inorganic or organic base, preferably pyridine, where R 3 is methyl or ethyl, R 2 is hydrogen and R, 3,4-dichlorophenyl or S-ChloM-methylphenyl.
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 erfindungsgemäßen Verbindungen erfolgt zweckmäßig in einer für eine Unkrautbekämpfung üblichen Weise in Form vorn 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 Dispergierhilfsniitteln.The compounds according to the invention are expediently used in a weed control usual way in the form of preparations such. B. Powders, grit, 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.
Die Herstellung der verschiedenen Zubereitungsformen erfolgt in an sich bekannter Art und Weise, z. B. durch Mahl- bzw. Mischverfahren.The various forms of preparation are produced in a manner known per se, for. 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 already 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.
Beispie! 1Example! 1
Im Gewächshaus wurden die in der Tabelle aufgeführten Verbindungen in einer Aufwandmenge von 10 kg Wirkstoff/ha, suspendiert in 8001 Wasser/ha, auf Senf und Tomaten als Testpflanzen gespritzt. Im Gegensatz zum Vergleichsmittel Isopropyl-N-phenyl-carbamat wurde eine Vernichtung der Testpflanzen erreicht.In the greenhouse, those listed in the table were Compounds at an application rate of 10 kg active ingredient / ha, suspended in 8001 water / ha, sprayed on mustard and tomatoes as test plants. In contrast to the comparison agent isopropyl-N-phenyl-carbamate destruction of the test plants was achieved.
Verbindung Nr.Connection no.
Senfmustard
Tomatentomatoes
Isopropyl-N-phenylcarbamat
ίο (gemäß deutscher PatentschriftIsopropyl N-phenyl carbamate
ίο (according to German patent specification
33 274)33 274)
= Total vernichtet.
= Keine Wirkung.= Totally destroyed.
= No effect.
1 2 01 2 0
1 71 7
4 1 34 1 3
Claims (5)
Nr.connection
No.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19661793751 DE1793751C3 (en) | 1966-02-03 | Diurethanes and herbicidal compositions containing them |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC036854 | 1965-04-09 | ||
| DE19661793751 DE1793751C3 (en) | 1966-02-03 | Diurethanes and herbicidal compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1793751A1 DE1793751A1 (en) | 1973-05-30 |
| DE1793751B2 DE1793751B2 (en) | 1975-07-24 |
| DE1793751C3 true DE1793751C3 (en) | 1976-03-04 |
Family
ID=
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