DE1901501B2 - M- TRIFLUOROMETHYLPHENYL URUBE AND HERBICIDAL AGENTS CONTAINING THESE - Google Patents
M- TRIFLUOROMETHYLPHENYL URUBE AND HERBICIDAL AGENTS CONTAINING THESEInfo
- Publication number
- DE1901501B2 DE1901501B2 DE19691901501 DE1901501A DE1901501B2 DE 1901501 B2 DE1901501 B2 DE 1901501B2 DE 19691901501 DE19691901501 DE 19691901501 DE 1901501 A DE1901501 A DE 1901501A DE 1901501 B2 DE1901501 B2 DE 1901501B2
- Authority
- DE
- Germany
- Prior art keywords
- och
- trifluoromethylphenyl
- urube
- agents containing
- herbicidal agents
- 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
Links
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
Description
X Sauerstoff oder Schwefel, isX oxygen or sulfur, is
R1 einen Ci-Cs-Alkylrest, der verzweigt und
durch 1 oder 2 Sauerstoffatome unterbrochen sein kann, einen C2-C4-Alkenyl-
oder Alinylrest,
R2 Wasserstoff oder einen Ct-Ci-Alkylrest,R 1 is a Ci-Cs-alkyl radical which can be branched and interrupted by 1 or 2 oxygen atoms, a C 2 -C4 alkenyl or alinyl radical,
R 2 is hydrogen or a Ct-Ci-alkyl radical,
oderor
R1 und R2 zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen heterocyclischen Ring mit 3 bis 6 Ringgliedern der auch ein Sauerstoffatom enthalten und/oder durch d-Gi-Alkylreste 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 d-Gi-alkyl radicals,
R3 einen Ci-Cs-Alkylrest, der verzweigt und durch Sauerstoff oder Schwefel unterbrochen sein kann, einen C2-CrAlkenyl- oder AlkinylrestR 3 is a Ci-Cs-alkyl radical, which can be branched and interrupted by oxygen or sulfur, a C2-Cr-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-(4-Methoxy-3-trifluormethylphenyl)-N'N'-dimethyl-harnstoff. 3. N- (4-methoxy-3-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-Isopropoxy-3-trifluormethylphenyl)-N'N'-dimethyl-harnstoff. 5. N- (4-isopropoxy-3-trifluoromethylphenyl) -N'N'-dimethyl urea.
6. N-(4-Äthoxyäthoxy-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.
Die neuen m-Trifluormethylphenylharnstoffe entsprechen der allgemeinen FormelThe new m-trifluoromethylphenylureas correspond the general formula
in derin the
R-'-XR -'- X
X Sauerstoff oder Schwefel,X oxygen or sulfur,
R1 einen Ci-Ca-Alkylrest, der verzweigt und durch 1 oder 2 Sauerstoffatome unterbrochen sein kann, einen CrC^-AIkenyl- oder Alkinylrest,R 1 is a Ci-Ca-alkyl radical, which can be branched and interrupted by 1 or 2 oxygen atoms, a CrC ^ -Alkenyl or alkynyl radical,
R2 Wasserstoff oder einen Ci-O-Alkylrest, oder
R' und R2 zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen heterocyclischen Ring
mit 3 bis 6 Ringgliedern, der auch ein Sauerstoffatom enthalten und/oder durch
Ci-G,-A!kylreste substituiert sein kann,
RJ einen Ci-Cs-Alkylrest, der verzweigt und
durch Sauerstoff oder Schwefel unterbrochen sein kann, einen Cj-C^AIkenyl- oder
AlkinylrestR 2 is hydrogen or a Ci-O-alkyl radical, or R 'and R 2 together with the nitrogen atom to which they are attached, a heterocyclic ring with 3 to 6 ring members, which also contain an oxygen atom and / or by Ci-G, -A! Kyl radicals can be substituted,
RJ a Ci-Cs-alkyl radical which can be branched and interrupted by oxygen or sulfur, a Cj-C ^ alkenyl or alkynyl radical
bedeuten.mean.
Ein günstiges Wirkungsspektrum haben jene Verbindungen, in denen X Sauerstoff bedeutet.Those compounds have a favorable spectrum of activity in which X is oxygen.
Die neuen m-Trifluormethylphenylharnstoffe der Formel I lassen sich nach an sich bekannten Methoden herstellen, durch Reaktion eines aromatischen RestesThe new m-trifluoromethylphenylureas der Formula I can be prepared by methods known per se, by reacting an aromatic radical
, .1 γ-, .1 γ-
-A-A
F,CF, C
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'
(wobei —CYYR' eine Estergruppe bedeutet)—N —CYYR '
(where —CYYR 'means an ester group)
3535
40 oder 40 or
-N — CY —Halogen-N - CY - halogen
-N-CY-NH2 -N-CY-NH 2
-N=C=Y-N = C = Y
4s 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 4s represents (with Y = O or S) and the other denotes the basic group -NH, in which the free valences are bonded to hydrogen, provided they are not constituents of a primary or secondary, including cyclic amine
sind, jeweils unter gegebenenfalls weiterer Nachalkylierung, und/oder Nachhalogenierung zu Gewinnung spezieller Vertreter der Formel I.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 I 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 I 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-Some of the connections also have defolian
65 Eigenschaften.65 properties.
Die Formulierung der neuen Harnstoffe der Formel 1 zu herbiziden Mitteln in trockener oder flüssiger Anwendung als Lösungen, Emulsionen, WettableThe formulation of the new ureas of formula 1 to herbicidal agents in dry or liquid Use as solutions, emulsions, wettables
19 Ol 50119 Ol 501
Powders, Stüubemittel geschieht in üblicher Weise und wird ausführlich in derPowders, dust is done in the usual way and is detailed in the
US-PS 33 29 702 oder
GB-PS 10 47 644 oder
CH-PS 4 24 359US-PS 33 29 702 or
GB-PS 10 47 644 or
CH-PS 4 24 359
beschrieben. In vielen Fällen ist die Anwendung von Granulaten zur gleichmäßigen, über einen längeren Zeitraum verteilten Wirkstoffabgabe von Vorteil. Solche Granulate lassen sich durch Lösen des Wirkstoffes in einem organischen Lösungsmittel, Absorption dieser Lösung durch granuliertes Mineral,described. In many cases, the use of granules is for even, over a longer period of time Distributed release of active ingredient over a period of time is advantageous. Such granules can be removed by dissolving the Active ingredient in an organic solvent, absorption of this solution by granulated mineral,
B Attapulgit oder SiO2 und Entfernen des Lösungsmittels herstellen.B Make attapulgite or SiO 2 and remove the solvent.
Jn Form der einen oder anderen Anwendung kann die Applikation solcher Mittel auch durch großflächige Verteilung (Versprühen oder Verstäuben) mit Hilfe von Flugzeugen durchgeführt werden.In the form of one or the other application, such agents can also be applied over large areas Distribution (spraying or dusting) can be carried out with the help of aircraft.
Die verschiedenen Anwendungsformen solcher Mittel können in üblicher Weise durch Zusatz von Stoffen, welche die Verteilung, die Haftfestigkeit, die Regenbeständigkeit und eventuell das Eindringungsvermögen verbessern, wie z. B. Fettsäuren, Harze, Netzmittel, Leim, Casein oder Alginate, den Verwendungszwecken näher angepaßt werden.The various forms of application of such agents can be carried out in the usual way by adding substances, which the distribution, the adhesive strength, the rain resistance and possibly the penetration capacity improve, such as B. fatty acids, resins, wetting agents, glue, casein or alginates, the uses be adjusted more closely.
Bei der Herstellung von herbizid wirksamen Mitteln kommen außerdem andere herbizide Wirkstoffe als Komponenten zur Kombination in Frage.In the manufacture of herbicidally active agents other herbicidal active ingredients are also suitable as components for the combination.
Die erfindungsgemäßen Mittel können auch in Kombination mit Insektiziden, Akariziden, Nematoziden, Bakteriziden, Fungiziden oder Molluskizide* verwendet werden.The agents according to the invention can also be used in combination with insecticides, acaricides, nematocides, Bactericides, fungicides or molluscicides * can be used.
s Im folgenden bedeuten Teile Gewichtsteile, die Temperaturen sind in Celsiusgraden angegeben.s In the following, parts mean parts by weight, which Temperatures are given in degrees Celsius.
33 Teile 4-Methoxy-3-trifluormethyl-phenylisocyanat werden in 50 cm3 Acetonitril gelöst und unter gutem Rühren zu einer Lösung von 20 cm3 Diethylamin (40%ige wässerige Lösung) in 100 cm3 Acetonitril getropft. Das Reaktionsprodukt wird mit Wasser gefällt und abfiltriert.33 parts of 4-methoxy-3-trifluoromethyl-phenyl isocyanate are dissolved in 50 cm 3 of acetonitrile and added dropwise with thorough stirring to a solution of 20 cm 3 of diethylamine (40% aqueous solution) in 100 cm 3 of acetonitrile. The reaction product is precipitated with water and filtered off.
F. 112 bis ILS CF. 112 to ILS C
CH3O -1CH 3 O -1
-NH-C-N-NH-C-N
CH.,CH.,
CH,CH,
[Verbindung Nr. I][Compound No. I]
Auf gleiche Weise wurden auch die folgenden Verbindungen erhalten:In the same way, the following compounds were also obtained:
Verbindung
Nr.link
No.
-- N-R' I R: - NR 'IR :
Schmelzpunkt CMelting point C.
1 OCH,1 OCH,
2 OCH3 2 OCH 3
N(CH,)2 112- 114 161 -166N (CH,) 2 112-114 161-166
OCH,OCH,
OCH,OCH,
CH3
NH-CH2-CH-C4H9 CH 3
NH-CH 2 -CH-C 4 H 9
C2H5
NH11C4H9
Nl11C3H7J2
NH-CH2-CH -=CH2 C 2 H 5
NH 11 C 4 H 9
Nl 11 C 3 H 7 J 2
NH-CH 2 -CH - = CH 2
CH -C = CHCH -C = CH
CH3 CH3 CH 3 CH 3
NHCH3
N — OCH,NHCH 3
STILL,
NH -CH2-CH(OCH3I2 NH -CH 2 -CH (OCH 3 I 2
N11C4H1,N 11 C 4 H 1 ,
CH,CH,
128 -131128 -131
öloil
106—107 80-89 129-130 öl106-107 80-89 129-130 oil
139—140 62--65139-140 62-65
97—101 66—6897-101 66-68
I N
I.
)\
)
5 Fortsetzung 5 continuation
Vorhiiuliini; XK1 N R' SchniL-l/piinklVorhiiuliini; XK 1 NR 'SchniL-l / piinkl
13 OCH, NCH2CH(OCH,), 89 9013 OCH, NCH 2 CH (OCH,), 89 90
14 OCH,14 OCH,
15 OCH,15 OCH,
16 OiC, H7 16 OiC, H 7
17 SCH,17 SCH,
18 OC2H5 18 OC 2 H 5
19 OC1H5 19 OC 1 H 5
cn,cn,
20 OC2H4OC2H5 N(CH,),20 OC 2 H 4 OC 2 H 5 N (CH,),
21 O11C., H7 N(CH,),21 O 11 C., H 7 N (CH,),
22 OCH2 — CH ClU N(CH,),22 OCH 2 - CH ClU N (CH,),
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-
setzu.ig hergestellt: cylmerkaptan mit 12MoI Äthylenoxid,additionally produced: cylmerkaptan with 12MoI ethylene oxide,
1,5% eines Kondensationsproduktes von p-Nonylphe-1.5% of a condensation product of p-nonylphe-
;ö nol mit 9 Mol Äthylenoxid.
50% eines im Beispiel 1 aufgeführten Wirkstoffes,; ö 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-Blattstadium, 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 zudem in Tabelle 2 dargestelltenIpomoea, Stellaria, Amaranthus, Avena, Gossypium, treatment and also performed as 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.
PflnnzenartPlant species
Triticum
I lordcum
Avena
ZeaTriticum
I lordcum
Avena
Zea
Digitaria
Sorghum
PanicumDigitaria
Sorghum
Panicum
Aus den Versuchsergebnissen ist ersichtlich, daß sich Verbindung 1 und 18 sowohl im Vorauflauf- 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-emergence 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.
Die zweimalige Auswertung nach 4 und 8 Wochen in ergab, daß alle aufgeführten Unkräuter vernichtet worden waren, die Weizenkultur aber völlig unangegriffen geblieben war.Two evaluations after 4 and 8 weeks showed that all the weeds listed had been destroyed but the wheat culture remained completely unaffected.
!> In einem gemäß Beispiel 3 geführten Versuch wurde im Vorauflaufverfahren, mit I kg/ha Aufwandmenge, die Verbindung Nr. 1 mit der aus der DT-PS 12 84 151 bekannten Verbindung N-(m-Trifluormethylphenyl)-N',N'-dimethyl-harnstoff(FluormeturonoderCotoran®) !> In an experiment carried out according to Example 3 was in the pre-emergence method, with an application rate of 1 kg / ha, compound no. 1 with that from DT-PS 12 84 151 known compound N- (m-trifluoromethylphenyl) -N ', N'-dimethyl urea (fluorometuron or Cotoran®)
•ίο verglichen. Es wurden die Pflanzen Triticum, Digitaria, Panicum und Alopecurus geprüft und folgende Resultate erhalten:• ίο compared. The plants Triticum, Digitaria, Panicum and Alopecurus tested and obtained the following results:
Verbindung iConnection i
In einem speziellen Feld-Test der Verbindung 1 in Winterweizen wurde folgendes Ergebnis erzielt.In a special field test of compound 1 in Winter wheat the following result was obtained.
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.
l-'luor-l-fluoro
mcturonmcturon
7 87 8
(l(l
Die Verbindung Nr. 1 erweist sich bei guter herbizide Wirkung als selektiv gegen Weizen.Compound no. 1 proves to be selective against wheat with good herbicidal activity.
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 true DE1901501B2 (en) | 1977-09-22 |
| DE1901501C3 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 |
| DE59005183D1 (en) * | 1989-11-10 | 1994-05-05 | Agrolinz Agrarchemikalien | Process for the production of pure, asymmetrically disubstituted ureas. |
| DE10029564A1 (en) | 2000-06-22 | 2002-01-03 | Continental Ag | elastomeric bearings |
| KR101116627B1 (en) | 2002-06-27 | 2012-10-09 | 노보 노르디스크 에이/에스 | Aryl carbonyl derivatives as therapeutic agents |
| MXPA06007667A (en) | 2004-01-06 | 2006-09-01 | Novo Nordisk As | Heteroaryl-ureas and their use as glucokinase activators. |
| ATE547396T1 (en) | 2005-07-08 | 2012-03-15 | Novo Nordisk As | DICYCLOALKYLCARBAMOYL UREAS AS GLUCOKINASE ACTIVATORS |
| AU2006268589B2 (en) | 2005-07-14 | 2011-09-29 | Vtv Therapeutics Llc | Urea glucokinase activators |
| EP2118083A1 (en) | 2007-01-09 | 2009-11-18 | Novo Nordisk A/S | Urea glucokinase activators |
| AU2008204530B2 (en) | 2007-01-11 | 2013-08-01 | Vtv Therapeutics Llc | Urea glucokinase activators |
| CN112040945A (en) | 2018-06-12 | 2020-12-04 | Vtv治疗有限责任公司 | Therapeutic use 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 IE IE80/69A patent/IE32624B1/en unknown
- 1969-01-21 SE SE6900757A patent/SE375095B/xx unknown
- 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
- 1969-01-22 NL NL6901066.A patent/NL159091B/en not_active IP Right Cessation
- 1969-01-23 RO RO58846A patent/RO54785A/ro unknown
- 1969-01-23 SU SU1300475A patent/SU404191A3/ru active
- 1969-01-23 BG BG11505A patent/BG17267A3/xx unknown
- 1969-01-23 GB GB3873/69A patent/GB1260386A/en not_active Expired
- 1969-01-23 CS CS45669*#A patent/CS158236B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1901501C3 (en) | 1978-05-03 |
| CS158236B2 (en) | 1974-10-15 |
| SE375095B (en) | 1975-04-07 |
| RO54785A (en) | 1973-05-17 |
| GB1260386A (en) | 1972-01-19 |
| DK124443B (en) | 1972-10-23 |
| DE1901501A1 (en) | 1969-08-28 |
| BG17267A3 (en) | 1973-07-25 |
| SU404191A3 (en) | 1973-10-26 |
| IL31444A (en) | 1973-03-30 |
| NL159091B (en) | 1979-01-15 |
| YU15469A (en) | 1979-10-31 |
| IE32624L (en) | 1969-07-23 |
| NL6901066A (en) | 1969-07-25 |
| FR2000570A1 (en) | 1969-09-12 |
| BE727286A (en) | 1969-07-22 |
| IL31444A0 (en) | 1969-03-27 |
| CH493195A (en) | 1970-07-15 |
| IE32624B1 (en) | 1973-10-03 |
| YU34874B (en) | 1980-04-30 |
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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 |