DE1901501C3 - m-Trifluoromethylphenylureas and herbicidal compositions containing them - Google Patents
m-Trifluoromethylphenylureas and herbicidal compositions containing themInfo
- Publication number
- DE1901501C3 DE1901501C3 DE1901501A DE1901501A DE1901501C3 DE 1901501 C3 DE1901501 C3 DE 1901501C3 DE 1901501 A DE1901501 A DE 1901501A DE 1901501 A DE1901501 A DE 1901501A DE 1901501 C3 DE1901501 C3 DE 1901501C3
- Authority
- DE
- Germany
- Prior art keywords
- och
- trifluoromethylphenylureas
- post
- compound
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
- C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
R-R-
inderin the
X Sauerstoff oder Schwefel,X oxygen or sulfur,
R1 einen Ci-Ce-Alkylrest, der verzweigt und durch 1 oder 2 Sauerstoffatome unterbrochen sein kann, einen C.2-C4-Alkenyl- oder Alkinylrest,R 1 is a Ci-C e -alkyl radical, which can be branched and interrupted by 1 or 2 oxygen atoms, a C.2-C4-alkenyl or alkynyl radical,
R2 Wasserstoff oder einen Ci-C^-Alkylrest,R 2 is hydrogen or a Ci-C ^ -alkyl radical,
oderor
R1 und R2 zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen heterocyclischen Ring mit 3 bis 6 Ringgliedern bilden, der auch ein Sauerstoffatom enthalten und/oder durch Ci-Gi-A!kylreste substituiert sein kann,R 1 and R 2 together with the nitrogen atom to which they are attached form a heterocyclic ring with 3 to 6 ring members, which can also contain an oxygen atom and / or be substituted by Ci-Gi-A! Kyl radicals,
R' einen Ci-Ce-Alkylrest, der verzweigt und durch Sauerstoff oder Schwefel unterbrochen sein kann, einen C2-Ci-Alkenyl- oder AlkinylrestR 'is a Ci-Ce-alkyl radical that is branched and can be interrupted by oxygen or sulfur, a C2-Ci-alkenyl- or alkynyl radical
bedeuten.mean.
2. Die Phenylharnstoffe der Formel I, in der X Sauerstoff bedeutet.2. The phenylureas of the formula I in which X is oxygen.
3. N -('♦-McthoxyO-trifluormethylphenyl)-N'N'-dimethyl-harnstoff. 3. N - ('♦ -MethoxyO-trifluoromethylphenyl) -N'N'-dimethyl urea.
4. N-(4-Äthoxy-3-trifluormethylphenyl)-N'N'-dimethyl-harnstoff. 4. N- (4-ethoxy-3-trifluoromethylphenyl) -N'N'-dimethyl urea.
5. N-(4-lsopropoxy-3-trifluormethylphenyl)-N'N'-dimethyl-harnstoff. 5. N- (4-isopropoxy-3-trifluoromethylphenyl) -N'N'-dimethyl urea.
6. N-(4-Äthcxyäthoxy-3-trifluormethylphenyl)-N'N'-dimethyl-harnstoff. 6. N- (4-Ethoxyethoxy-3-trifluoromethylphenyl) -N'N'-dimethyl urea.
7. Selektive herbizide Mittel zur Unkrautbekämpfung in Weizenkulturen, enthaltend als Wirkstoff mindestens eine Verbindung der allgemeinen Formel des Anspruchs 1.7. Selective herbicidal compositions for controlling weeds in wheat crops, containing as active ingredient at least one compound of the general formula of claim 1.
R1 und R2 zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen heterocyclischen Ring mit 3 bis 6 Ringgliedern bilden, der auch ein Sauerstoffatom enthalten und/oder durch Ci-Cj-Alkylreste substituiert sein kann, R1 einen Ci-C8-Alkylrest, der verzweigt und durch Sauerstoff oder Schwefel unterbrochen sein kann, einen C2-C)-Alkenyl- oder AlkinylrestR 1 and R2 together with the nitrogen atom to which they are attached form a heterocyclic ring with 3 to 6 ring members, which can also contain an oxygen atom and / or be substituted by Ci-Cj-alkyl radicals, R 1 is a Ci-C 8 -Alkyl radical, which can be branched and interrupted by oxygen or sulfur, a C2-C) -alkenyl or alkynyl radical
bedeuten.mean.
Ein günstiges Wirkungsspektrum haben jene Verbindungen, in denen X Sauerstoff bedeutetThose compounds in which X means oxygen have a favorable spectrum of activity
Die neuen m-Trifluormethylphenylharnstoffe der Formel I lassen sich nach an sich bekannten Methoden herstellen, durch Reaktion eines aroma iischen RestesThe new m-trifluoromethylphenylureas der Formula I can be prepared by methods known per se, by reacting an aromatic residue
Die neuen m-Trifluormethylphenylharnstoffe entsprechen der allgemeinen FormelThe new m-trifluoromethylphenylureas correspond the general formula
in derin the
X Sauerstoff oder Schwefel,X oxygen or sulfur,
R1 einen Ci-C8-Alkylrest, der verzweigt und durch 1 oder 2 Sauerstoffatome unterbrochen sein kann, einen C.2-C.4-Alkenyl- oder Alkinylrest,R 1 is a Ci-C 8 -alkyl radical which can be branched and interrupted by 1 or 2 oxygen atoms, a C.2-C.4-alkenyl or alkynyl radical,
:,-A!ky!rest,oder R-'-X:, - A! Ky! Rest, or R -'- X
)—A) —A
mit einem zweiten Reaktionspartner B, die beide zusammen die Harnstoffgruppierung gemäß Formel I zu bilden vermögen. Darin haben X und R3 die für Formel I gegebene Bedeutung, während einer der Substituenten A oder B die Gruppierungwith a second reactant B, both of which together are able to form the urea grouping according to formula I. Here, X and R 3 have the meaning given for formula I, while one of the substituents A or B is the grouping
— N-CYYR'- N-CYYR '
(wobei —CYYR' eine Estergruppe bedeutet)(where —CYYR 'means an ester group)
-N-CY-Halogen-N-CY halogen
— N—CY-NH,- N-CY-NH,
-N=C=Y-N = C = Y
darstellt (mit Y = O oder S) und der andere die basische Gruppe -NH bedeutet, in der die freien Valenzen an Wasserstoff gebunden sind, soweit sie nicht Bestandteile eines primären oder sekundären, auch cyclischen Amins sind, jeweils unter gegebenenfalls weiterer Nachalkylierung, und/oder Nachhalogenierung zu Gewinnung spezieller Vertreter der Formel I.represents (with Y = O or S) and the other means the basic group -NH, in which the free valences are Hydrogen are bonded to the extent that they are not constituents of a primary or secondary, including cyclic, amine are to be obtained, in each case with further post-alkylation and / or post-halogenation, if appropriate special representative of formula I.
Die neuen Verbindungen der Formel 1 besitzen vornehmlich selektive Wirkung gegen Unkräuter in Nutzpflanzenkulturen. Die Wirkung läßt sich im Vorauflaufverfahren und im Nachauflaufverfahren erzielen und wird vornehmlich in wichtigen Großkulturen wie Getreide, Reis, Mais, Soja, Baumwolle und anderen beobachtet. Totalherbizide Wirkung tritt bei höheren Aufwandmengen ein, die immer dann von Vorteil ist, wenn der Nutzboden für eine neue Pflanzung vorbereitet werden soll, während noch Überreste einer vorherigen Kultur vorhanden sind.The new compounds of formula 1 have primarily selective action against weeds in Crops of useful plants. The effect can be achieved in the pre-emergence method and in the post-emergence method and is mainly used in major large-scale crops such as grain, rice, corn, soy, cotton and others observed. Total herbicidal effect occurs at higher application rates, which is always an advantage when the soil is to be prepared for a new planting while there are still remains of one previous culture are present.
Die Verbindungen haben auch teilweise Defolians-Eigenschaften. Some of the connections also have defolian properties.
Die Formulierung der neuen Harnstoffe der Formel I zu herbiziden Mitteln in trockener oder flüssiger Anwendung als Lösungen, Emulsionen, WettableThe formulation of the new ureas of the formula I into herbicidal agents in dry or liquid Use as solutions, emulsions, wettables
I 19 Ol 501I 19 Ol 501
j 3 4j 3 4
I Powders, Stäubemittel geschieht in üblicher Weise und Die erfindungsgemäßen Mittel können auch inI Powders, dusting agents are done in the usual way and The agents according to the invention can also be used in
I wird ausführlich in der Kombination mit Insektiziden, Akariziden, Nematozi-I is detailed in the combination with insecticides, acaricides, nematocides
I den. Bakteriziden, Fungiziden oder MoüuskizidenI den. Bactericides, fungicides or muskicides
\ , US-PS 33 29 702 oder verwendet werden. \ , US-PS 33 29 702 or can be used.
J GB-PS 10 47 644 oder 5 Im folgenden bedeuten Teile Gewichtsteile, dieJ GB-PS 10 47 644 or 5 In the following, parts mean parts by weight, the
I CH-PS4 24 359 Temperaturen sind in Celsiusgraden angegeben.I CH-PS4 24 359 Temperatures are given in degrees Celsius.
I beschrieben. In vielen Fällen ist die Anwendung vonI described. In many cases the application of
I Granulaten zur gleichmäßigen, über einen längeren Beispiel 1I Granules for uniform, over a longer period of time Example 1
1 Zeitraum verteilten Wirkstoffabgabe von Vorteil. io1 period of time distribution of active ingredient is advantageous. ok
j Solche Granulate lassen sich durch Lösen des 33 Teile 4-Methoxy-3-trifluormethy!-phenylisocyanat j Such granules can be prepared by dissolving the 33 parts of 4-methoxy-3-trifluormethy! -phenyl
J Wirkstoffes in einem organischen Lösungsmittel, werden in 50 cm3 Acetonitril gelöst und unter gutemJ active ingredient in an organic solvent are dissolved in 50 cm 3 of acetonitrile and taken under good
I Absorption dieser Lösung durch granuliertes Mineral, Rühren zu einer Lösung von 20 cm3 DimethylaminI absorption of this solution by granulated mineral, stirring to a solution of 20 cm 3 of dimethylamine
'· z. B. Attapulgit oder S1O2 und Entfernen des Lösungs- (40%ige wässerige Lösung) in 100 cm3 Acetonitril 'Z. B. attapulgite or S1O2 and removing the solution (40% aqueous solution) in 100 cm 3 of acetonitrile
mittels herstellen. 15 getropft. Das Reaktionsprodukt wird mit Wasser gefälltby means of manufacture. 1 5 dripped. The reaction product is precipitated with water
I In Form der einen oder anderen Anwendung kann die und abfiltriert.I In the form of one application or another, the and can be filtered off.
I Applikation solcher Mittel auch durch großflächigeI Application of such agents also through large areas
? Verteilung (Versprühen oder Verstäuben) mit Hilfe von F. 112 bis 115 C? Distribution (spraying or dusting) with the help of F. 112 to 115 C.
ί Flugzeugen durchgeführt werden. Pj,ί aircraft are carried out. Pj,
; Die verschiedenen Anwendungsformen solcher Mit- 20 / 3 ; The various forms of application of such co-20 / 3
i tel können in üblicher Weise durch Zusatz von Stoffen, πι π ^ ^ NH —C M i tel can in the usual way by adding substances, πι π ^ ^ NH —CM
welche die Verteilung, die Haftfestigkeit, die Regenbe- ^niu \ ^ \ \which the distribution, the adhesive strength, the rain- ^ n i u \ ^ \ \
ständigkeit und eventuell das Eindringungsvermögen / JL rj-ipersistence and possibly the penetration capacity / JL rj-i
verbessern, wie z. B. Fettsäuren, Harze, Netzmittel, F,C 3 improve, such as B. fatty acids, resins, wetting agents, F, C 3
Leim, Casein oder Alginate, den Verwendungszwecken 25Glue, casein or alginate, the uses 25
näher angepaßt werden. [Verbindung Nr. I]be adjusted more closely. [Compound No. I]
Bei der Herstellung von herbizid wirksamen MittelnIn the manufacture of herbicidally active agents
kommen außerdem andere herbizide Wirkstoffe als Auf gleiche Weise wurden auch die folgendenIn addition, other herbicidal ingredients come in the same way as the following
Komponenten zur Kombination in Frage. Verbindungen erhalten:Components for combination in question. Get connections:
- N — R1 Schmelzpunkt- N - R 1 melting point
R2 CR 2 C
N(CH,)2 112—114N (CH,) 2 112-114
N j 161 — 166N j 161 - 166
OCH, N O 128—131OCH, NO 128-131
"Λ"Λ
CH,
OCH, NH-CH2-CH-C4Ho ölCH,
OCH, NH-CH 2 -CH-C 4 Ho oil
C2H5 C 2 H 5
NHnC4H, 106—107NH n C 4 H, 106-107
N(„C,H7)2 86—89N ( "C, H 7) 2 86-89
NH-CH2-CH=CH2 129—130NH-CH 2 -CH = CH 2 129-130
N CH — C = CH ölN CH - C = CH oil
I II I
CH, CH,CH, CH,
NHCH, 139-140NHCH, 139-140
N — OCH, 62-65N-OCH, 62-65
Nil -CH2-CH(OCH,), 97 ΙΟΙNil -CH 2 -CH (OCH,), 97 ΙΟΙ
N11C4H4 66 68N 11 C 4 H 4 66 68
Nr.link
No.
19 Ol 50119 Ol 501
5 65 6
Fortsetzungcontinuation
Verhindern;; XR1 N R1 Sdimd/nunkiImpede;; XR 1 NR 1 Sdimd / nunki
K9 90K9 90
tSTILL,
t
66 70 K)X 109 65 6766 70 K) X 109 65 67
Es wurde ein Spritzpulver der folgenden Zusammen- 3,5% eines Kondensationsproduktes von 1 Mol Dode-It was a wettable powder of the following composition- 3.5% of a condensation product of 1 mol of dodec-
setzung hergestellt: cylmerkaptan mit 12 Mol Äthylenoxid.Settlement produced: Cylmerkaptan with 12 moles of ethylene oxide.
1,5% eines Kondensationsproduktes von p-Nonylphe-1.5% of a condensation product of p-nonylphe-
.15 nol mit 9 Mol Äthylenoxid.
50% eines im Beispiel 1 aufgeführten Wirkstoffes,.15 nol with 9 moles of ethylene oxide.
50% of an active ingredient listed in Example 1,
25% Bolus alba (Kaolin), Die so erhaltene, feingemahlene Mischung läßt sich in25% Bolus alba (kaolin), the finely ground mixture obtained in this way can be used in
20% feinverteiltes SiO2 (unter dem Markennamen beliebiger Weise mit Wasser zu einer gebrauchsfertigen20% finely divided SiO 2 (under the brand name any way with water to make a ready-to-use
»Hisil« im Handel befindliches Produkt), Spritzbrühe verdünnen.»Hisil« commercially available product), dilute the spray liquid.
Im Gewächshaus werden Tontöpfe mit Erde gefüllt wässerigen Lösung einer der im Beispiel 1 beschriebe-In the greenhouse, clay pots are filled with earth, an aqueous solution of one of the described in Example 1-
und mit mehreren der folgenden Samenarten angesät: nen Verbindungen ca. 10 bis 12 Tage nach der Aussaat,and sown with several of the following types of seeds: nen compounds approximately 10 to 12 days after sowing,
Triticum vulgäre, Hordeum vulgaris, Beta vulgaris, 45 im 2-3-Blatts.tadium, in einer Aufwandmenge von 2 kgTriticum vulgäre, Hordeum vulgaris, Beta vulgaris, 45 in the 2-3 leaf stage, at an application rate of 2 kg
Calendula, Chrysanthemum, Sinapis arvensis, Lepidium Aktivsubstanz pro Hektar.Calendula, Chrysanthemum, Sinapis arvensis, Lepidium active ingredient per hectare.
sativum, Digitaria, Poa, Alopecurus, Linum, Brassica, Die Auswertung erfolgte ca. 20 Tage nach dersativum, Digitaria, Poa, Alopecurus, Linum, Brassica, The evaluation took place approx. 20 days after the
Ipomoea, Stellaria, Amaranthus, Avena, Gossypium, Behandlung und führte zu dem in Tabelle 2 dargestelltenIpomoea, Stellaria, Amaranthus, Avena, Gossypium, treatment and resulted in that shown in Table 2
Zea, Oryza, Sorghum, Panicum, Cynodon veg., Galium, Ergebnis.Zea, Oryza, Sorghum, Panicum, Cynodon veg., Galium, Result.
Soja. 50 Die Preemergent-Behandlung erfolgte mit gleicherSoy. 50 The pre-emergent treatment was carried out with the same
Die Postemergent-Behandlung der genannten Pflan- Aufwandmenge vor dem Aufkeimen, 24 Stunden nachPost-emergent treatment of the above-mentioned plant application rate before germination, 24 hours after
zenarten erfolgte mit einer l%igen und 0,06%igen der Aussaat.zenarten took place with a 1% and 0.06% of the sowing.
PflanzenartPlant species
Triticum HordeumTriticum Hordeum
Digitaria Sorghum l'nnirtimDigitaria Sorghum l'nnirtim
19 Ol 50119 Ol 501
Fortsetzungcontinuation
l'llan/.cnurtl'llan / .cnurt
Verbindulli;Connections;
Postpost
Verbindung 1Connection 1
l're Verbindung
18l're connection
18th
Postpost
Verbindung !8Connection! 8
l'rel're
Verbindung 20Connection 20
Postpost
Alopecurus 7 8Alopecurus 7 8
Cynodon veg.Cynodon veg.
GossypiumGossypium
Galium 6Galium 6
Calendula 7 9Calendula 7 9
Chrysanthemum - -Chrysanthemum - -
Linum -Linum -
BrassicaBrassica
Ipomoea 9 9Ipomoea 9 9
Stellaria 9 9Stellaria 9 9
Amaranthus 9 6Amaranthus 9 6
Bewertung:Valuation:
1-3 = Pflanze nicht oder kaum beeinträchtigt.
4-6 = Mittlere Schaden.
7-8 = Schwere Schaden.1-3 = plant not or hardly affected.
4-6 = Medium damage.
7-8 = severe damage.
Aus den Versuchsergebnissen ist ersichtlich, daß sich Verbindung 1 und 18 sowohl im Vorauf lauf- wie im Nachauflaufverfahren als Unkrautbekämpfungsmittel in Weizenkulturen empfehlen. Verbindung 18 ist als typisches selektives Herbizid zum Schütze von Baumwollkulturen bei Vorauflauf-Applikation anzusehen. Als Unkrautvernichtungsmittel in Mais-Kulturen empfiehlt sich Verbindung 20, die insbesondere dort von Vorteil ist, wo langjährige Applikation von Triazinderivaten zur Unkrautvernichtung nicht mehr den gewünschten Erfolg hat, weil einstmals unbedeutende Unkrautarten heute in den Vordergrund getreten sind, die von diesen Triazinen kaum angegriffen werden.From the test results it can be seen that compound 1 and 18 both in the pre-running as in the Recommend post-emergence methods as a weed control agent in wheat crops. Compound 18 is as typical selective herbicide for protecting cotton crops in pre-emergence application. as Weedkillers in maize crops, compound 20 is recommended, which is particularly advantageous there is where long-term application of triazine derivatives for weed control is no longer the desired one Success is because once insignificant weed species have now come to the fore, those of these Triazines are hardly attacked.
In einem speziellen Feld-Test der Verbindung 1 in Winterweizen wurde folgendes Ergebnis erzielt.The following result was obtained in a special field test of compound 1 in winter wheat.
Im Frühjahr wurde zur Zeit der Bestockung ein Winterweizenfeld mit 1 kg AS/ha behandelt, das von den natürlichen Unkräutern Alopecurus, Poa trivialis, Apera spica-venti, Geranium, Veronica, Matricaria, Myosotis, Arabidopsis, Stellaria und Sinapis befallen war.In spring, a winter wheat field was treated with 1 kg AS / ha at the time of tillering the natural weeds Alopecurus, Poa trivialis, Apera spica-venti, Geranium, Veronica, Matricaria, Myosotis, Arabidopsis, Stellaria and Sinapis was infested.
9
9
99
9
9
9
9
9
99
9
9
9
9 ο9 ο
9 99 9
Die zweimalige Auswertung nach 4 und 8 Wochen ergab, daß alle aufgeführten Unkräuter vernichtet worden waren, die Weizenkultur aber völlig unangegriffen geblieben war.The evaluation twice after 4 and 8 weeks showed that all the weeds listed were destroyed but the wheat culture remained completely unaffected.
in einem gemäß Beispiel 3 geführten Versuch wurde im Vorauflaufverfahren, mit 1 kg/ha Aufwandmenge die Verbindung Nr. 1 mit der aus der DT-PS 12 84 151 bekannten Verbindung N-(m-Trifluormethylphenyl)-Ν',Ν'-dimethyl-harnstoff (Fluormeturon oder Cotoran®] verglichen. Es wurden die Pflanzen Triticum, Digitaria Panicum und Alopecurus geprüft und folgende Resultate erhalten:In a test carried out according to Example 3, the pre-emergence method was carried out with an application rate of 1 kg / ha Compound no. 1 with the compound N- (m-trifluoromethylphenyl) -Ν ', Ν'-dimethylurea known from DT-PS 12 84 151 (Fluormeturon or Cotoran®]. The plants Triticum, Digitaria Panicum and Alopecurus tested and obtained the following results:
Verbindung ICompound I
Fluermeturon Fluermeturon
6 Alopecurus 7 46 Alopecurus 7 4
Die Verbindung Nr. 1 erweist sich bei guter herbizide Wirkung als selektiv gegen Weizen.Compound No. 1 proves to be good herbicidal Effect as selective against wheat.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH102268A CH493195A (en) | 1968-01-23 | 1968-01-23 | Pesticides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1901501A1 DE1901501A1 (en) | 1969-08-28 |
| DE1901501B2 DE1901501B2 (en) | 1977-09-22 |
| DE1901501C3 true DE1901501C3 (en) | 1978-05-03 |
Family
ID=4200614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1901501A Expired DE1901501C3 (en) | 1968-01-23 | 1969-01-14 | m-Trifluoromethylphenylureas and herbicidal compositions containing them |
Country Status (15)
| Country | Link |
|---|---|
| BE (1) | BE727286A (en) |
| BG (1) | BG17267A3 (en) |
| CH (1) | CH493195A (en) |
| CS (1) | CS158236B2 (en) |
| DE (1) | DE1901501C3 (en) |
| DK (1) | DK124443B (en) |
| FR (1) | FR2000570A1 (en) |
| GB (1) | GB1260386A (en) |
| IE (1) | IE32624B1 (en) |
| IL (1) | IL31444A (en) |
| NL (1) | NL159091B (en) |
| RO (1) | RO54785A (en) |
| SE (1) | SE375095B (en) |
| SU (1) | SU404191A3 (en) |
| YU (1) | YU34874B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3222974A1 (en) * | 1982-06-19 | 1983-12-22 | Basf Ag, 6700 Ludwigshafen | NEW 5-PHENOXYBENZISOTHIAZOL-4'-UREA DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| ES2062248T3 (en) * | 1989-11-10 | 1994-12-16 | Agrolinz Agrarchemikalien | PROCEDURE FOR OBTAINING PURE UREAS, ASYMMETRICALLY DISUBSTITUTED. |
| DE10029564A1 (en) | 2000-06-22 | 2002-01-03 | Continental Ag | elastomeric bearings |
| EP1531815B1 (en) | 2002-06-27 | 2014-09-24 | Novo Nordisk A/S | Glucokinase activators |
| PT1723128E (en) | 2004-01-06 | 2013-02-27 | Novo Nordisk As | Heteroaryl-ureas and their use as glucokinase activators |
| US7999114B2 (en) | 2005-07-08 | 2011-08-16 | Novo Nordisk A/S | Dicycloalkylcarbamoyl ureas as glucokinase activators |
| US7884210B2 (en) | 2005-07-14 | 2011-02-08 | Novo Nordisk A/S | Ureido-thiazole glucokinase activators |
| WO2008084043A1 (en) | 2007-01-09 | 2008-07-17 | Novo Nordisk A/S | Urea glucokinase activators |
| AU2008204530B2 (en) | 2007-01-11 | 2013-08-01 | Vtv Therapeutics Llc | Urea glucokinase activators |
| CA3093025A1 (en) | 2018-06-12 | 2019-12-19 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
-
1968
- 1968-01-23 CH CH102268A patent/CH493195A/en not_active IP Right Cessation
-
1969
- 1969-01-14 DE DE1901501A patent/DE1901501C3/en not_active Expired
- 1969-01-16 FR FR6900613A patent/FR2000570A1/fr not_active Withdrawn
- 1969-01-19 IL IL31444A patent/IL31444A/en unknown
- 1969-01-21 SE SE6900757A patent/SE375095B/xx unknown
- 1969-01-21 IE IE80/69A patent/IE32624B1/en unknown
- 1969-01-22 NL NL6901066.A patent/NL159091B/en not_active IP Right Cessation
- 1969-01-22 YU YU154/69A patent/YU34874B/en unknown
- 1969-01-22 BE BE727286D patent/BE727286A/xx unknown
- 1969-01-22 DK DK34469AA patent/DK124443B/en unknown
- 1969-01-23 BG BG11505A patent/BG17267A3/xx unknown
- 1969-01-23 RO RO58846A patent/RO54785A/ro unknown
- 1969-01-23 GB GB3873/69A patent/GB1260386A/en not_active Expired
- 1969-01-23 SU SU1300475A patent/SU404191A3/ru active
- 1969-01-23 CS CS45669*#A patent/CS158236B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE375095B (en) | 1975-04-07 |
| YU15469A (en) | 1979-10-31 |
| IE32624L (en) | 1969-07-23 |
| RO54785A (en) | 1973-05-17 |
| YU34874B (en) | 1980-04-30 |
| CS158236B2 (en) | 1974-10-15 |
| NL6901066A (en) | 1969-07-25 |
| GB1260386A (en) | 1972-01-19 |
| BE727286A (en) | 1969-07-22 |
| DE1901501A1 (en) | 1969-08-28 |
| FR2000570A1 (en) | 1969-09-12 |
| DK124443B (en) | 1972-10-23 |
| CH493195A (en) | 1970-07-15 |
| BG17267A3 (en) | 1973-07-25 |
| SU404191A3 (en) | 1973-10-26 |
| IL31444A0 (en) | 1969-03-27 |
| IE32624B1 (en) | 1973-10-03 |
| NL159091B (en) | 1979-01-15 |
| IL31444A (en) | 1973-03-30 |
| DE1901501B2 (en) | 1977-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |