DE2208329A1 - 2-substd-4-trialkylsilylamino-6-amino-s-triazines - - with herbicidal and plant growth regulating activity - Google Patents
2-substd-4-trialkylsilylamino-6-amino-s-triazines - - with herbicidal and plant growth regulating activityInfo
- Publication number
- DE2208329A1 DE2208329A1 DE19722208329 DE2208329A DE2208329A1 DE 2208329 A1 DE2208329 A1 DE 2208329A1 DE 19722208329 DE19722208329 DE 19722208329 DE 2208329 A DE2208329 A DE 2208329A DE 2208329 A1 DE2208329 A1 DE 2208329A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- triazine
- acid
- triazines
- chloro
- 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.)
- Pending
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 8
- 230000008635 plant growth Effects 0.000 title 1
- 230000001105 regulatory effect Effects 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
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- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 239000011230 binding agent Substances 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 5
- 239000011707 mineral Substances 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 239000004009 herbicide Substances 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 3
- 239000004480 active ingredient Substances 0.000 claims description 40
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- 239000003795 chemical substances by application Substances 0.000 claims description 12
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- 238000000034 method Methods 0.000 claims description 8
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
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- 239000000460 chlorine Substances 0.000 claims description 5
- JSQLYLIRGCVEOL-UHFFFAOYSA-N n-trimethylsilyl-1,3,5-triazin-2-amine Chemical class C[Si](C)(C)NC1=NC=NC=N1 JSQLYLIRGCVEOL-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
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- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
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- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FHYUCVWDMABHHH-UHFFFAOYSA-N toluene;1,2-xylene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1C FHYUCVWDMABHHH-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Verfahren zur Herstellung neuer herbizid wirksamer s-Triazin-Derivate Die vorliegende Erfindung betrifft neue Trialkylsilylaminos-triazine, Verfahren zu ihrer Herstellung, weiterhin herbizide Mittel, die als Wirkstoffe solche s-Triazine enthalten und Verfahren zur Bekämpfung grasartiger und zweikeimblättriger Unkräuter unter Verwendung der neuen Wirkstoffe oder der sie enthaltenden Mittel.Process for the preparation of new herbicidally active s-triazine derivatives The present invention relates to new trialkylsilylaminos-triazines, processes for their production, furthermore herbicidal compositions which contain such s-triazines as active ingredients and methods for controlling grassy and dicotyledon weeds using the new active ingredients or the compositions containing them.
Die neuen Trialkylsilylamino-s-triazine entsprechen der Formel 1: In dieser Formel bedeuten: R1 die Cyano- oder Azidogruppe 5 Halogen, einen Alkoxy-oder Alkylthiorest, R2 einen Alkyl-, Alkenyl-, Alkinyl-, Cycloalkyl- oder Alkoxyalkylrest oder einen gegebenenfalls durch Cycloalkyl substituierten Cyanoalkylrest und R3 einen Alkylrest.The new trialkylsilylamino-s-triazines correspond to formula 1: In this formula: R1 denotes the cyano or azido group 5 halogen, an alkoxy or alkylthio group, R2 denotes an alkyl, alkenyl, alkynyl, cycloalkyl or alkoxyalkyl group or a cyanoalkyl group optionally substituted by cycloalkyl and R3 denotes an alkyl group.
Unter einem Alkylthio- oder Alkoxyrest R1 sind niedere Reste mit: 1 bis 4 Kohlenstoffatomen zu verstehen, bevorzugt sind der Mcthylthio-, Aethylthio- und Methoxyrest. Halogen kann Chlor, Brom oder Fluor sein, vorzugsweise jedoch Chlor. In der allgemeinen Formel 1 weisen Alkylrest R2 und R3 in gerader oder verzweigter Kette 1 bis 8 Kohlenstoffatome auf; in Frage kommen zum Beispiel der Methyl-, Aethyl-, Propyl- und Isopropylrest sowie der Butyl Pentyl-, Hexyl-, Heptyl- und Octylrest und deren Isomere. FUr R3 kommen insbesondere der Methyl-, Aethyl-, Propyl- und Isopropylrest in Frage. Ein solcher Alkylrest, ein- oder mehrfach durch niedere Alkoxyreste oder durch eine Cyanogruppe substituiert, bildet auch einen Alkoxyalkyl- oder Cyanoalkylrest R2. Als Cycloalkylreste R2 kommen der Cyclopropyl-, Cyclobutyl-, Cyclopentyl-oder Cyclohexylrest in Betracht; diese Reste können ausserdem Substituenten eines Cyanoalkylrestes sein. Unter Alkenyl- oder Alkinylresten R2 sind solche mit 2 bis 6 Kohlenstoffatomen zu verstehen, bevorzugt sind der Allyl-, Methallyl- oder ein anderer Propenylrest sowie ein gegebenenfalls durch Alkyl substituierter Propinylrest. Under an alkylthio or alkoxy radical R1 are lower radicals with: 1 to 4 carbon atoms to be understood, preferred are the methylthio, ethylthio and methoxy radical. Halogen can be chlorine, bromine or fluorine, but preferably chlorine. In general formula 1, the alkyl radicals R2 and R3 are straight or branched chain 1 to 8 carbon atoms; for example, methyl, ethyl, Propyl and isopropyl radical as well as the butyl pentyl, hexyl, heptyl and octyl radical and their isomers. For R3, there are in particular methyl, ethyl, propyl and Isopropyl radical in question. Such an alkyl radical, one or more times through lower Alkoxy radicals or substituted by a cyano group, also forms an alkoxyalkyl or cyanoalkyl radical R2. Cycloalkyl radicals R2 are the cyclopropyl, cyclobutyl, Cyclopentyl or cyclohexyl radicals into consideration; these radicals can also have substituents be a cyanoalkyl radical. Alkenyl or alkynyl radicals R2 are those with 2 to 6 carbon atoms to be understood, preferred are the allyl, methallyl or another propenyl radical and a propynyl radical which is optionally substituted by alkyl.
Von besonderer Bedeutung sind Trialkylsilylamino-s-triazine der Formel II: in der R und R2 die unter Formel I angegebenen Bedeutungen haben und Rl insbesondere für Chlor, den Methoxy-oder Methylthio-Rest steht.Trialkylsilylamino-s-triazines of the formula II are of particular importance: in which R and R2 have the meanings given under formula I and Rl in particular represents chlorine, the methoxy or methylthio radical.
Die neuen Trialkylsilylamino-s-triazine der Formel I werden gemäss vorliegender Erfindung erhalten, indem man ein Diaminos-triazin der Formel III a) in Gegenwart einer starken Mineralsäure, vorzugsweise konzentrierter Schwefelsflure, mit einem Hexaalkyldisilazan der Formel (R3)3- Si-NH- Si -oder b) in Gegenwart eines säurebindenden Mittels mit einem Trialkylchlorsilan der Formel (R3)3SiCl umsetzt und ein gegebenenfalls noch vorhandenes Chloratom R1 gewUnschtenfalls in an sich bekannter Weise durch die Azido- oder Cyanogruppe, eine Allcylthio- oder Alkoxygruppe oder durch ein anderes Halogenatom ersetzt.The new trialkylsilylamino-s-triazines of the formula I are obtained according to the present invention by adding a diaminos-triazine of the formula III a) in the presence of a strong mineral acid, preferably concentrated sulfuric acid, with a hexaalkyldisilazane of the formula (R3) 3-Si-NH-Si - or b) in the presence of an acid-binding agent with a trialkylchlorosilane of the formula (R3) 3SiCl and optionally one existing chlorine atom R1 is replaced, if desired, in a manner known per se by the azido or cyano group, an alkylthio or alkoxy group or by another halogen atom.
In den Formeln II und III haben R1 und R2 die unter Formel I angegebenen Bedeutungen.In formulas II and III, R1 and R2 have the values given under formula I. Meanings.
Die Umsetzung eines Diamino-s-triazins mit einem ilexaalkyldisilazan erfolgt in Gegenwart einer starken Mineralsäure, insbesondere konzentrierter Schwefelsäure, oder eines Gemisches von konzentrierter Schwefelsäure mit anderen starken Mineralsäuren unter Erhitzen am RUckfluss. The reaction of a diamino-s-triazine with an ilexaalkyldisilazane takes place in the presence of a strong mineral acid, especially concentrated sulfuric acid, or a mixture of concentrated sulfuric acid with other strong mineral acids with reflux heating.
Bei der Silylierung mit einem Trialkylchlorsilan ist es zweckmässig, ein säurebindendes Mittel zuzusetzen. In Betracht kommen anorganische Basen, wie Alkali- und Erdalkalimetallhydroxide, -hydrogencarbonate und -carbonate, ferner vorzugsweise Amine, wie Trialkylamine, Pyri.din und Pyridinbasen. Ebenso kann aber auch die jeweilige Aminokomponente, im Ueberschuss eingesetzt, als säurebindendes Mittel dienen.In the case of silylation with a trialkylchlorosilane, it is useful to to add an acid-binding agent. Inorganic bases such as Alkali and alkaline earth metal hydroxides, bicarbonates and carbonates, furthermore preferably amines such as trialkylamines, pyridine and pyridine bases. But also can also the respective amino component, used in excess, as an acid-binding agent Serving means.
Beide Umsetzungen werden in gegenüber den Reaktionsteilnehmern inerten Lösungs- oder Verdunnungsmitteln durchgeführt, zum Beispiel in aliphatischen, aromatischen oder halogenierten Kohlenwasserstoffen, wie Benzol, Toluol, Xylolen, Chlorbenzol; Aethern und ätherartigen Verbindungen; Nitrilen; Amiden; Ketonen; Estern; Sulfoxiden, usw. sowie Gemischen solcher Lösungsmittel untereinander. Die Reaktionstemperaturen liegen zwischen 15° und 140°, vorzugsweise zwischen 60° und 100°. Both reactions are inert towards the reactants Solvents or diluents carried out, for example in aliphatic, aromatic or halogenated hydrocarbons such as benzene, toluene, xylenes, chlorobenzene; Ethers and ethereal compounds; Nitriles; Amides; Ketones; Esters; Sulfoxides, etc. as well as mixtures of such solvents with one another. The reaction temperatures are between 15 ° and 140 °, preferably between 60 ° and 100 °.
Die fakultative Einführung eines Alkoxy- oder Alkylthiorestes sowie der Cyano- oder Azidogruppe oder eines Brom- oder Fluoratoms in Verbindungen der Formel I, in denen R1 Chlor bedeutet, erfolgt in bekannter Weise durch Umsetzung mit- einem Alkalimetallsalz eines Alkanols oder Mercapt-ans mit einem Alkali- oder Ammoniumsalz von Blausäure, Stickstoffwasserstoffsäure oder einer entsprechenden HalogenwasserstoffsSure. Der Austausch lasst sich auch bewerkstelligen, indem man von den entsprechenden Alkanolen, Mercaptanen oder Säuren ausgeht und diese in Gegenwart einer oben beschriebenen Base, insbesondere Trimethylamin, umsetzt. FUr diese Umsetzungen werden gegenüber den Reaktionsteilnehmern inerte, vorzugsweise mit Wasser mischbare Lösungsmittel verwendet; beispielsweise Ketone, wie Aceton, Methyläthylketon, etc., Dioxan und Dimethylformamid. The optional introduction of an alkoxy or alkylthio radical as well as the cyano or azido group or a bromine or fluorine atom in compounds of Formula I in which R1 is chlorine is carried out in a known manner by reaction with an alkali metal salt of an alkanol or mercaptan with an alkali or Ammonium salt of hydrocyanic acid, hydrazoic acid or an equivalent Hydrohalic acid. The exchange can also be achieved by contacting the appropriate Alkanols, mercaptans or acids goes out and these in the presence of one of the above Base, especially trimethylamine, reacts. For these conversions are opposite the reactants inert, preferably water-miscible solvents used; for example ketones such as acetone, methyl ethyl ketone, etc., and dioxane Dimethylformamide.
Die Ausgangsstoffe der Formel III, in denen Rl ein Chloratom bedeutet, können aus Cyanurchlorid durch Umsetzung mit einem Mol Ammoniak und einem Mol eines Amins der Formel H2HR2 hergestellt werden. Ein gegebenenfalls noch vorhandenes Chloratom kann durch Umsetzung mit Alkali- oder Ammoniumsalzen von Alkanolen, Mercaptanen, etc. nach den vorher beschriebenen Verfahren ausgetauscht werden. The starting materials of the formula III, in which Rl is a chlorine atom, can be made from cyanuric chloride by reaction with one mole of ammonia and one mole of one Amine of the formula H2HR2 can be produced. Any chlorine atom still present can by reaction with alkali or ammonium salts of alkanols, mercaptans, etc. can be exchanged according to the previously described procedure.
Die folgenden Beispiele dienen zur Veranschaulichung des erfindungsgemässen Verfahrens. Weitere Trialkylsilylamino-s-triazine, die nach den in den Beispielen beschriebenen Verfahren hergestellt wurden, finden sich in der sich daran anschliessenden Tabelle. The following examples serve to illustrate the invention Procedure. Further trialkylsilylamino-s-triazines according to the in the examples The process described can be found in the subsequent Tabel.
Die Temperaturen sind in Grad Celsius angegeben.The temperatures are given in degrees Celsius.
Beispiel 1 9,35 g 2-Chlor-4-isopropylamino-6-amino-s-triazin werden in 100 ml absolutem Benzol suspendiert. Dann tropft man bei Raumtemperatur 4,5 g Hexamethyldisilazan in 30 ml absolutem Benzol zu, fügt einen Tropfen konzentrierte Schwefelsäure bei und lässt das Gemisch 48 Stunden am Pvückfluss sieden. Nach dem Abkühlen wird die benzolische Lösung abgetrennt, mit Wasser gewaschen, getrocknet und eingedampft. Der RUckstand wird aus Cyclohexan umkristallisiert; man erhält 2-Chlor-4-isopropylamino-6-(trimethylsilylamino)-s-triazin mit dem Schmelzpunkt 145° - 147° beispiel 2 18,4 g 2-Methoxy-4-isopropylamino-6-amino-s-triazin werden in 200 ml absolutem Benzol gelöst. Bei Raumtemperatur werden zuerst 10,1 g Triäthylamin und anschliessend 10,9 g Trimethylchlorsilan in 50 ml absolutem Benzol zugetropft. Man erwärmt auf 60° - 65° und lässt 48 Stunden rühren. Danach wird die 6enzolische Lösung abgetrennt, mit Wasser gewaschen, getrocknet und eingedampft.Example 1 9.35 g of 2-chloro-4-isopropylamino-6-amino-s-triazine become suspended in 100 ml of absolute benzene. 4.5 g are then added dropwise at room temperature Hexamethyldisilazane in 30 ml of absolute benzene, adds a drop of concentrated Sulfuric acid and lets the mixture reflux for 48 hours. After this After cooling, the benzene solution is separated off, washed with water and dried and evaporated. The residue is recrystallized from cyclohexane; you get 2-chloro-4-isopropylamino-6- (trimethylsilylamino) -s-triazine with the melting point 145 ° - 147 ° Example 2 18.4 g of 2-methoxy-4-isopropylamino-6-amino-s-triazine are dissolved in 200 ml of absolute benzene. At room temperature it will first be 10.1 g of triethylamine and then 10.9 g of trimethylchlorosilane in 50 ml of absolute benzene added dropwise. The mixture is heated to 60 ° -65 ° and allowed to stir for 48 hours. After that, the 6enzolische solution separated, washed with water, dried and evaporated.
Der Rückstand wird im Hochvakuum bei 130°-132°/0,001 mm destilliert.The residue is distilled in a high vacuum at 130 ° -132 ° / 0.001 mm.
Das anschliessend kristallisierende 2-Methoxy-4-isopropylamino-6-(trimethylsilylamino)-s-triazin
hat den Schmelzpunkt 38° - 400.
Die Aufwandmengen sind verschieden und vom Applikationszeitpunkt abhängig, sie liegen zwischen 0,1 - 10 kg Wirkstoff pro Hektar, bei Applikation vor dem Auflaufen der Pflanzen bis zu 4 kg Wirkstoff pro Hektar und nach dem Auflaufen der Pflanzen bei 3 bis 10 kg Wirkstoff pro Hektar, wobei für eine solche totale Vernichtung des gesamten Unkrautbestandes, beispielsweise auf Kulturland benachbartem Brachland, Eisenbahndämmen, Fabrikanlagen oder Autostrassen mehr als 10 kg Wirkstoff pro Hektar angewendet werden müssen. Die übliche Fruchtfolge kann bei Anwendung der neuen Wirkstoffe ohne Beeinträchtigung erfolgen. The application rates are different and depend on the time of application depending, they are between 0.1 - 10 kg of active ingredient per hectare, when applied before emergence of the plants up to 4 kg of active ingredient per hectare and after emergence of the plants at 3 to 10 kg of active ingredient per hectare, for such a total Destruction of the entire weed population, for example on neighboring cultivated land Fallow land, railway embankments, factories or highways have more than 10 kg of active ingredient must be applied per hectare. The usual crop rotation can be applied when applying of the new active ingredients take place without impairment.
Ausserdem können solche Triazine auch als Wachstumsregulatoren, beispielsweise zur Entblätterung, Verminderung des FruchLansatzes, Verzögerung der Blume, etc. eingesetzt werden. In addition, such triazines can also be used as growth regulators, for example for defoliation, reduction of the fruit set, delaying the flower, etc. can be used.
1. Herbizide Wirkung bei Applikation der Wirkstoffe vor dem Auflaufen der Pflanzen (preemergence-Appliltation) Unmittelbar nach der Einsaat der Testpflanzen werden die Wirkstoffe als wässrige Suspension, erhalten aus einem 25%igen Spritzpulver, auf die Erdoberfläche appliziert. Dann werden die Saatschalen bei 22° - 25° und 50 - 70 7o relativer Luftfeuchtigkeit gehalten. Nach 28 Tagen wird der Versuch ausgewertet.1. Herbicidal effect when the active ingredients are applied before emergence of the plants (preemergence application) Immediately after the test plants have been sown the active ingredients as an aqueous suspension, obtained from a 25% wettable powder, applied to the surface of the earth. Then the seed trays are at 22 ° - 25 ° and Maintained 50 - 70 7o relative humidity. The experiment is evaluated after 28 days.
Als Testpflanzen wurden verwendet: Kulturpflanzen: Weizen (Triticum
vulgare) Unkräuter: Lolium perenne Sinapis alba Galium aparine Pastinaca sativa
Setaria italica Poa trivialis Alopecurus myosuorides Digitaria sanguinalis Echinochloa
crus galli Amaranthus docendens Chrysanthemum segetum Die jeweiligen Aufwandmengen
in diesem Versuch finden sich in den folgenden Tabellen la, ib und lc. Die Bonitierung
erfolgt nach dem 9er Index: 9 = Pflanzen ungeschädigt (Kontrolle) 1 = Pflanzen abgestorben
2-8 = Zwischenstufen der Schädig
Tabeklle 1 a
Die jeweiligen Aufwandmengen sind in der folgenden Tabelle 2 angegeben.The respective application rates are given in Table 2 below.
Tabelle 2
C) Phenole Dinitro-sec-hutylphenol oder Salze davon Pentachlorphenol oder Salze davon.C) phenols dinitro-sec-hutylphenol or salts thereof pentachlorophenol or salts thereof.
3,5-Dinitro-o-kresol 2,6-Dibrom-4-cyanphenol 2,6-Dichlor-4-cyanphenol Salze + Ester Dinitro-tert-butylphenol Salze + Ester Dinitro-sec-arnyl-phenol Salze + Ester 2-Aethoxymethyl-4,6-dinitrophenol Salze + Ester 2-tert. Butyl-4,6-dinitro-5-methylphenol Salze + Ester D) Carbonsäuren, Salze und Ester 2,4,6-Trichlorphenylessigsäure 2,3,6-Trichlorbenzoesäure und Salze -2,3,5,6-Tetrachlorbenzoesäure und Salze 2,3,5,6-Tetrachlorterephalsäure 2-Methoxy-3,5,6-trichlorbenzoesäure und Salze Cyclopropancarbonsäure-2,4-dinitro-6-sec. butylphenylester Cyclopentancarbonsäure-2,4-dinitro-6-sec. butylphenylester 2-Methoxy-3,6-dichlorbenzoesäure und Salze 2-Amino-2,5-dichlorbenzoesäure und Salze 3-Nitro-2,5-dichlorbenzoesure und Salze 2-Methyl-3,6-dichlorbenzoesaure und Salze 2,4-Dichlorphenoxyessigsäure, Salze und Ester 2,4,5-Trichlorphenoxyessigsäure, Salze und Ester (2-Methyl-4-chlorphenoxy)essigsäure, Salze und Ester 2-(2,4,5-Trichlorphenoxy)propionsäure, Salze und Ester 2-(2,4,5-Trichlorphenoxy)äthyl-2,2-dichlorpropionsäure, Salze und Ester 4-(2,4-Dichlorphenoxy) buttersäure, Salze und Ester 4-(2-Methyl-4-chlorphenoxy)buttersäure, Salze + Ester Methyl-2-chlor-3-(4' -chlorphenyl)-propionat 2-Chlor-9-hydroxy-fluoren-9-carbonsäure Endo-oxo-hexahydrophthalslure Tetrachlorphthalsäuredimethylester 4-Chlor-2-oxobenzothiazolin-3-yl-essigsäukre 2,2,3-Trichlorpropionsure Salze + Ester 2,2-Dichlorpropionsäure Salze + Ester (+)2-(2,4-Dichlorphenoxy)-propionsäure Salze + Ester 7-Oxabicyclo (2,2,1) heptano-2,3-dicarbonsäure 4-Chlorphenc>xyessigsäure Salze + Ester Gibberellinsäure Indolylcssi gs'iurc Indolylbuttersäure (#)2-(4-chloro-2-methylphenoxy) propionsäure Salze + Ester N, N-Diallylchloracetamid Naphthylessigsäure N-l-Naphthylphthalimidsäure Salze + Ester 4-Amino-3,5,6-trichlor-picolinsäure Salze + Ester Trichloressigsäure 4-(2,4,5-Trichlorphenoxy)buttersäure Salze f Ester 2,3,5-Trijodbenzoesäure Salze + Ester Benzimidoxyessigsäure Salze + Ester Aethylenglykol-bis-trichloracetat Chloressigsäurediäthylamid 2,6-Dichlorthiobenzamid 2,6-Dichlorbenzonitril N,N-Dimethyl-α-α-diphenylacetamid Diphenylacetonitril N-Hydroxymethyl-2,6-dichlorthiobenzamid E) Carbaminsäurederivate Carbanilsäure-isopropylester 3,4-Dichlor-carbanilsäure-methylester m-Chlor-carbanilsäure-isopropylester m-Chlor-carbanilsäure-4-chlor-2-butinylester m-Trifluormethyl-carbanilsäure-isopropylester 2,6-Di-tert. butyl-4-tolyl-N-methylcarbamat 3-(Methoxycarbonylamino) phenyl-N-3-tolylcarbamat 4-Chlor-2-butinyl-N-(3-chlorphenyl)-carbamat Methyl-2-isopropyl-4-(methylcarbamoyloxy)carbanilat ferner Diallat, N,N-Dipropyl-S-äthylthiocarbamat, Molinate und Dithiocarbamate der Formel worin R1, R2 und R3 einen niederen Alkyl- oder Alkenylrest bedeuten, oder worin R1 und R2 zusammen mit dem mit ihnen verbundenen Stickstoffatom einen 5-, 6- oder 7-gliedrigen, gegebenenfalls alkylierten Ring mit insgesamt 6 oder 7 C-Atomen darstellen, wobei die exo-Alkylgruppen an den, dem Stickstoffatom benachbarten, Kohlenstoffatomen gebunden sein müssen, und R3 den Aethyl-, Propyl-, n-Butylrest oder Isobutylrest darstellt, darunter besonders N-tyl-N-äthyl-S-propyl-dithiocarbamat N,N-Diisobutyl-S-propyl-dithiocarbamat N,N,S-Tripropyldithiocarbamat N-Isobutyl-N-allyl-S-propylidithiocarbamat N-Isobutyl-N-methallyl-S-äthyldithiocarbamat N-Isobutyl-N-methallyl-S-propyldithiocarbamat N,N-Dimethallyl-S-propyldithiocarbamat N-Butyl-N-äthyl-S-propyl-thiocarbamat und N,N,S-Tripropylthiocarbamat, sowie N-(4-Aminobenzsulfonyl) methylcarbamat 1-Methylprop-2-yl-N-(3-chlorphenyl) carbamat Isopropyl-N-(3-chlorphenyl)-carbamat S-2,3-Dichlorallyl-N,N-diisopropylthiocarbamat S-Aethyl-N,N-dipropylthiocarbamat N-Methyldithiocarbaminsäure S-propyl-N-butyl-N-äthylthiocarbamat 3-(m-Tolylcarbamoyloxy)-phenylcarbamat Isopropyl-N-phenylcarbamat 2-Chlorallyl-N,N-diäthyldithiocarbamat Methyl-N-(3,4-dichlorphenyl) carbamat S-2,3,3-Trichlorallyl-N,N-diisopropylthiolcarbamat S-Propyl-N,N-dipropylthiolcarbamat S-Acetyl-N-äthylthiocyclohexancarbamat 3,4-Dichlorbenzylmethylcarbamat S-Aethyl-N-hexahydrol-1H-azepinthiolcarbamat 2,6-Di-t-butyl--methylphenyl-N-methyl-carbamat Methyl-N-(4-nitrobenzsulfonyl) carbamat N,N-Hexamethylen-S-isopropyl-thiocarbamat S-Aethyl-N,N-Diisobutylthiolcarbamat 2-Chlorbutinyl-N-(3-chlorphenyl) carbamat S-Acethyl-N,N-diisobutylthiolcarbamat Methyl-N'-(N'-methoxycarbamoyl-sulfanilyl) carbamat F) Anilide 3,4-Dichlorpropionanilid 3-Chlor-4-brompropionanilid 3-Brom-4-chlorpropionanilid Cyclopropancarbonsäure-3,4-dichloranilid Cyclopropancarbonsäure-3-chlor-4-bromanilud Cyclopropancarbonsäure-3-brom-4-chloranilid N-(3,4-Dichlorphenyl)-2-methylpentamid N-1-Naphthyl-phthalaminsäure N-(3-Tolyl)-phthalaminsäure 2-Methacryl-3', 4'-dichlor-anilid N-(4-Chlorphenyl)-2,2,-dimethylvaleramid N-(3-Chlor-4-methylphenyl)-2-methylpentanamid α-Chlor-N-isopropylacetanilid 2-(α-naphtoxy)-N,N-diäthylpropionamid 2-Chlor-N-(2-methyl-6-tert. butylphenyl) acetamid 2-Chloro-N-2,6-diäthylphenyl-N-methoxymethylacetamid 6-Methyl-N-methoxymethyl-2-t-butyl-α-bromacetanilid 2-[(4-Chlor-o-tolyl)oxy]-N-methoxyacetamid 2-Chlor-N-isopropyl-acetanilid G) Organische Phosphorverbindungen tris-(2,4-Dichlorphenoxyäthyl) phosphit 0-(2,4-Dichlorphenyl)-O'-methyl-N-isopropyl-amidothiophosphat N-[2-(O,O-Di-isopropyldithiophosphoryl) äthyl]-benzolsulfonamid S,S,S-Tributyl-thiophosphat H) Verschiedene Verbindungen 4,5-Dichlor-2-trifluormethylbenzimidazol 2-Chloräthyl-trimethyl-ammoniumchlorid Maleinsäurehydrazid Methylarsinsaure-di-Na-Salz 4,5,7-Trichlorbenzthiodiazol-2,1,3 3-Amino-1,2,4-triazol Trichlorbenzylchlorid 2-Phenyl-3,1-benzoxazinon N-Butyl-N-äthyl-2,6-dinitro-4-trifluormethylanilin N,N-Di-(n-propyl)-2,6-dinitro-4-trifluormethylanilin 4-Trifluormethyl-2,4'-dinitro-diphenyläther 2,4,6-Trichlor-4'-nitrodiphenyläther 4-Trifluormethyl-2,4f-dinitro-3'-methyl-diphenyläther 2,4-Dichlor-4'-nitro-diphenyläther 5-Chlor-6-methyl-3-tert.butyluracil Ammoniumsulfamat 5-Brom-6-methyl-3-(1-methyl-N-propyl)-uracil 1,2,4,5,6,7,10,10-Octachlor-4,7,8,9-tetrahydro-4,7-methylenindan-m-isopropyl-xanthat 5-Brom-3-isopropyl-6-methyluracil 3-Cyclohexyl-6-methyluraci.l 3-Cyclohexyl-6-sec. butyluracil 3-Cyclohexyl-5-bromuracil 3-Cyclohexyl-5-chloruracil 3-Cyclohexyl-5,6-trimethylen-uracil 3-lsopropyl-5-chioruracil 3-Isopropyl-5-bromuracil 2-Chlor-N-äthyl-4-rhodanoanilin 2,3,6-Trichlorbenzyloxypropanol Hexachloro-2-propanon Mstrium-2-(2,4,5-trichlorphenoxy)-äthyl Kaliumcyanat 3,5-Dibrom-4-hydroxybenzaldoxim-2', 4'-dinitrophenyläther 3,5-Dijod-4-hydroxybenzaldoxim-2', 4'-dinitrophenyläther Acrolein Arsenate Allylalkohol 2,4-Dinitrophenyl-2,4-dinitro-6-sec. butylphenylcarbonat 5-Chlor-2-isopropylbenzimidazol 5-Jod-2-trifluoromethylbbenzimidazol 3-Cyclohexyl-6,7-dihydro-1H-cyclopentapyrimidin-2,4-(3H, 5H) dion 1:1-Aethylen-2:2-bipyridyliumbromid 1,1-Dimethyl-4,4'-bipyridylium-dimethylsulfat Di(methoxythiocarbonyl) disulfid 2-Methyl-4-(3'-trifluoromethylphenyl) tetrahydro-1,2,4-oxadiazin-3,5-dion 1-Phenyl-4,5-dimethoxy-6-pyridazon 6-Chlor-2-difluormethy13H-imidazol (4,5-b)-pyridin 2-tert. Butyl-6-chlorimidazol-4,5-pyridin 5-Amino-4-brom-2-phenylpyridazin-3-on Hexafluoracetonhydrat 3,5-Dinitre-4-dipropylamino-benzolsulfonamid Kakodyl 4-(Methylsulphonyl)-2,6-dinitro-N,N-dipropylanilin 4-Methyl-2,6-dinitro-N,N-dipropylanilin 5-Amino-4-chlor-2-phenyl-3-pyridazon 2,3,5-Trichlor-4-pyridinol 3,4,5,6-tetrahydro-3,5-dimethyl-1,3,5-thiadiazin-2-thion Natrium-2-(2,4-dichlorphenoxy) äthylsulfat 2,3-Dichlor-1,4-naphthochinon Di (äthoxythiocarbonyl) disulfid 3,5-Dichlor-2,6-difluor-4-hydroxy-pyridin Die Herstellung erfindungsgemässer herbizider Mittel erfolgt in an sich bekannter Weise durch inniges Vermischen und Vermahlen von Wirkstoffen der allgemeinen Formel I mit geeigneten Trägerstoffen, gegebenenfalls unter Zusatz von gegenüber den Wirkstoffen inerten Dispersions- oder Lösungsmitteln. Die Wirkstoffe können in den folgenden Aufarbeitungsformen vorliegen und angewendet werden: feste Aufarbeitungsformen : Stäubemittel, Streumittel, Granulate, Umhüllungsgranulate, Impränierungsgranulate und Homogengranulate, in Wasser dispergierbare Wirks toffkenzentrate: Spritzpulver, (wettable powder), Pasten, Enulsionen; flüssige Aufarbeitungsformen : Lösungen.3,5-dinitro-o-cresol 2,6-dibromo-4-cyanophenol 2,6-dichloro-4-cyanophenol salts + ester dinitro-tert-butylphenol salts + ester dinitro-sec-arnyl-phenol salts + ester 2- Ethoxymethyl-4,6-dinitrophenol salts + ester 2-tert. Butyl-4,6-dinitro-5-methylphenol salts + esters D) Carboxylic acids, salts and esters 2,4,6-trichlorophenylacetic acid 2,3,6-trichlorobenzoic acid and salts -2,3,5,6-tetrachlorobenzoic acid and salts 2 , 3,5,6-tetrachloroterephalic acid 2-methoxy-3,5,6-trichlorobenzoic acid and salts cyclopropanecarboxylic acid-2,4-dinitro-6-sec. butylphenyl ester cyclopentanecarboxylic acid 2,4-dinitro-6-sec. butylphenyl ester 2-methoxy-3,6-dichlorobenzoic acid and salts 2-amino-2,5-dichlorobenzoic acid and salts 3-nitro-2,5-dichlorobenzoic acid and salts 2-methyl-3,6-dichlorobenzoic acid and salts 2,4-dichlorophenoxyacetic acid , Salts and esters 2,4,5-trichlorophenoxyacetic acid, salts and esters (2-methyl-4-chlorophenoxy) acetic acid, salts and esters 2- (2,4,5-trichlorophenoxy) propionic acid, salts and esters 2- (2, 4,5-trichlorophenoxy) ethyl-2,2-dichloropropionic acid, salts and esters 4- (2,4-dichlorophenoxy) butyric acid, salts and esters 4- (2-methyl-4-chlorophenoxy) butyric acid, salts + ester methyl-2 chloro-3- (4'-chlorophenyl) propionate 2-chloro-9-hydroxy-fluorene-9-carboxylic acid endo-oxo-hexahydrophthalic acid dimethyl tetrachlorophthalate 4-chloro-2-oxobenzothiazolin-3-yl-acetic acid 2,2,3 -Trichloropropionic acid salts + ester 2,2-dichloropropionic acid salts + ester (+) 2- (2,4-dichlorophenoxy) propionic acid salts + ester 7-oxabicyclo (2,2,1) heptano-2,3-dicarboxylic acid 4-chlorophenc > xyacetic acid salts + ester gibberellic acid indoly lcssi gs'iurc indolylbutyric acid (#) 2- (4-chloro-2-methylphenoxy) propionic acid salts + ester N, N-diallylchloroacetamide naphthyl acetic acid Nl-naphthylphthalimidic acid salts + ester 4-amino-3,5,6-trichloropicolinic acid salts + Ester trichloroacetic acid 4- (2,4,5-trichlorophenoxy) butyric acid salts f ester 2,3,5-triiodobenzoic acid salts + ester benzimidoxyacetic acid salts + ester ethylene glycol bis-trichloroacetate chloroacetic acid diethylamide 2,6-dichlorothiobenzamide 2,6-dichlorobenzonitrile N, N -Dimethyl-α-α-diphenylacetamide Diphenylacetonitrile N-Hydroxymethyl-2,6-dichlorothiobenzamide E) Carbamic acid derivatives Carbanilic acid isopropyl ester 3,4-dichlorocarbanilic acid methyl ester m-chlorocarbanilic acid isopropyl ester m-chlorocarbanilic acid 4-chloro 2-butynyl ester, m-trifluoromethylcarbanilic acid, isopropyl ester, 2,6-di-tert. butyl 4-tolyl-N-methylcarbamate 3- (methoxycarbonylamino) phenyl-N-3-tolylcarbamate 4-chloro-2-butynyl-N- (3-chlorophenyl) -carbamate, methyl-2-isopropyl-4- (methylcarbamoyloxy) carbanilate also dialate, N, N-dipropyl-S-ethylthiocarbamate, molinates and dithiocarbamates of the formula in which R1, R2 and R3 represent a lower alkyl or alkenyl radical, or in which R1 and R2 together with the nitrogen atom connected to them represent a 5-, 6- or 7-membered, optionally alkylated ring with a total of 6 or 7 carbon atoms, where the exo-alkyl groups must be bonded to the carbon atoms adjacent to the nitrogen atom, and R3 represents the ethyl, propyl, n-butyl radical or isobutyl radical, including especially N-tyl-N-ethyl-S-propyl-dithiocarbamate N, N-diisobutyl-S-propyl-dithiocarbamate N, N, S-tripropyldithiocarbamate N-isobutyl-N-allyl-S-propylidithiocarbamate N-isobutyl-N-methallyl-S-ethyldithiocarbamate N-isobutyl-N-metharbamate N-isobutyl-N-metharbamate , N-dimethallyl-S-propyldithiocarbamate, N-butyl-N-ethyl-S-propyl-thiocarbamate and N, N, S-tripropylthiocarbamate, as well as N- (4-aminobenzsulfonyl) methylcarbamate 1-methylprop-2-yl-N- ( 3-chlorophenyl) carbamate isopropyl-N- (3-chlorophenyl) -carbamate S-2,3-dichloroallyl-N, N-diisopropylthiocarbamate S-ethyl-N, N-dipropylthioc arbamat N-methyldithiocarbamic acid S-propyl-N-butyl-N-ethylthiocarbamate 3- (m-tolylcarbamoyloxy) -phenylcarbamate isopropyl-N-phenylcarbamate 2-chloroallyl-N, N-diethyldithiocarbamate methyl-N- (3,4-dichamlorophenyl) S-2,3,3-trichloroallyl-N, N-diisopropylthiol carbamate S-propyl-N, N-dipropylthiol carbamate S-acetyl-N-ethylthiocyclohexane carbamate 3,4-dichlorobenzylmethylcarbamate S-ethyl-N-hexahydrol-1H-azepinthiol Di-t-butyl-methylphenyl-N-methyl-carbamate Methyl-N- (4-nitrobenzsulfonyl) carbamate N, N-hexamethylene-S-isopropyl-thiocarbamate S-ethyl-N, N-diisobutylthiol carbamate 2-chlorobutinyl-N - (3-chlorophenyl) carbamate S-Acethyl-N, N-diisobutylthiolcarbamate methyl-N '- (N'-methoxycarbamoyl-sulfanilyl) carbamate F) anilides 3,4-dichloropropionanilide 3-chloro-4-bromopropionanilide 3-bromo-4 -chlorpropionanilide cyclopropanecarboxylic acid-3,4-dichloroanilide cyclopropanecarboxylic acid-3-chloro-4-bromanilud cyclopropanecarboxylic acid-3-bromo-4-chloroanilide N- (3,4-dichlorophenyl) -2-methylpentamide N-1-naphthyl-phthalamine acid N- (3-tolyl) -phthalamic acid 2-methacryl-3 ', 4'-dichloro-anilide N- (4-chlorophenyl) -2,2, -dimethylvaleramide N- (3-chloro-4-methylphenyl) -2 -methylpentanamide α-chloro-N-isopropylacetanilide 2- (α-naphtoxy) -N, N-diethylpropionamide 2-chloro-N- (2-methyl-6-tert. butylphenyl) acetamide 2-chloro-N-2,6-diethylphenyl-N-methoxymethylacetamide 6-methyl-N-methoxymethyl-2-t-butyl-α-bromoacetanilide 2 - [(4-chloro-o-tolyl) oxy] - N-methoxyacetamide 2-chloro-N-isopropyl-acetanilide G) Organic phosphorus compounds tris- (2,4-dichlorophenoxyethyl) phosphite 0- (2,4-dichlorophenyl) -O'-methyl-N-isopropyl-amidothiophosphate N- [2 - (O, O-Di-isopropyldithiophosphoryl) ethyl] -benzenesulfonamide S, S, S-Tributyl-thiophosphate H) Various compounds 4,5-dichloro-2-trifluoromethylbenzimidazole 2-chloroethyl-trimethyl-ammonium chloride Maleic acid hydrazide Methylarsinic acid-di-Na- Salt 4,5,7-trichlorobenzothiodiazole-2,1,3 3-amino-1,2,4-triazole trichlorobenzyl chloride 2-phenyl-3,1-benzoxazinone N-butyl-N-ethyl-2,6-dinitro-4 trifluoromethylaniline N, N-di (n-propyl) -2,6-dinitro-4-trifluoromethylaniline 4-trifluoromethyl-2,4'-dinitro-diphenyl ether 2,4,6-trichloro-4'-nitrodiphenyl ether 4-trifluoromethyl -2,4f-dinitro-3'-methyl-diphenyl ether 2,4-dichloro-4'-nitro-diphenyl ether 5-chloro-6-methyl-3-tert.butyluraci l ammonium sulfamate 5-bromo-6-methyl-3- (1-methyl-N-propyl) -uracil 1,2,4,5,6,7,10,10-octachloro-4,7,8,9-tetrahydro -4,7-methylenindan-m-isopropyl-xanthate 5-bromo-3-isopropyl-6-methyluracil 3-cyclohexyl-6-methyluraci.1 3-cyclohexyl-6-sec. butyluracil 3-cyclohexyl-5-bromouracil 3-cyclohexyl-5-chloruracil 3-cyclohexyl-5,6-trimethylene-uracil 3-isopropyl-5-chioruracil 3-isopropyl-5-bromouracil 2-chloro-N-ethyl-4- rhodanoaniline 2,3,6-trichlorobenzyloxypropanol hexachloro-2-propanone mstrium-2- (2,4,5-trichlorophenoxy) -ethyl potassium cyanate 3,5-dibromo-4-hydroxybenzaldoxime-2 ', 4'-dinitrophenyl ether 3,5- Diiodo-4-hydroxybenzaldoxime-2 ', 4'-dinitrophenyl ether acrolein arsenate allyl alcohol 2,4-dinitrophenyl-2,4-dinitro-6-sec. butylphenyl carbonate 5-chloro-2-isopropylbenzimidazole 5-iodo-2-trifluoromethylbbenzimidazole 3-cyclohexyl-6,7-dihydro-1H-cyclopentapyrimidine-2,4- (3H, 5H) dione 1: 1-ethylene-2: 2-bipyridylium bromide 1,1-dimethyl-4,4'-bipyridylium-dimethylsulfate di (methoxythiocarbonyl) disulfide 2-methyl-4- (3'-trifluoromethylphenyl) tetrahydro-1,2,4-oxadiazine-3,5-dione 1-phenyl- 4,5-dimethoxy-6-pyridazon 6-chloro-2-difluoromethyl13H-imidazole (4,5-b) -pyridine 2-tert. Butyl-6-chloroimidazole-4,5-pyridine 5-amino-4-bromo-2-phenylpyridazin-3-one hexafluoroacetone hydrate 3,5-dinitre-4-dipropylamino-benzenesulfonamide kakodyl 4- (methylsulphonyl) -2,6-dinitro -N, N-dipropylaniline 4-methyl-2,6-dinitro-N, N-dipropylaniline 5-amino-4-chloro-2-phenyl-3-pyridazone 2,3,5-trichloro-4-pyridinol 3,4 , 5,6-tetrahydro-3,5-dimethyl-1,3,5-thiadiazine-2-thione sodium 2- (2,4-dichlorophenoxy) ethyl sulfate 2,3-dichloro-1,4-naphthoquinone di (ethoxythiocarbonyl ) disulfide 3,5-dichloro-2,6-difluoro-4-hydroxypyridine The herbicidal compositions according to the invention are prepared in a manner known per se by intimately mixing and grinding active ingredients of the general formula I with suitable carriers, optionally with the addition of opposite the active ingredients inert dispersants or solvents. The active ingredients can be present and used in the following working-up forms: solid working-up forms: dusts, scattering agents, granules, coated granules, impregnation granules and homogeneous granules, water-dispersible active ingredients: wettable powders, pastes, enulsions; liquid forms of preparation: solutions.
Zur Herstellung fester Aufarbeitungsformen (Stäubemittel, Streumittel, Granulate), werden die Wirkstoffe mit festen Trägerstoffen vermischt. Als Trägerstoffe kommen zum Beispiel Kaolin, Talkum, Bolus, Löss, Kreide, Kalkstein, Kalkgrits, Ataclay, Dolomit, Diatomeenerde, gefällte Kieselsäure, Erdalkalisilikate, Natrium- und Kaliumaluminiumsilikate (Feldspäte und Glimmer), Calcium- und Magnesiumsulfate, Magnesiumoxyd, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat,Ammoniumphosphat, Ammoniumnitrat. Harnstoff, gemahlene, pflanzliche Produkte, wie Getreidemehl, Baumrindemebl, Holzmehl, Nusschalenmehl, Collulosepulver, Rückstände von Pflanzenextraktionen, Aktivkohle, ctc., > je für sich oder als Mischungen untereinander in Frage. For the production of solid processing forms (dust, grit, Granules), the active ingredients are mixed with solid carriers. As carriers for example kaolin, talc, bolus, loess, chalk, limestone, lime grit, ataclay, Dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminum silicates (Feldspars and mica), calcium and magnesium sulphates, magnesium oxide, ground Plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate. Urea, ground, vegetable products such as grain flour, tree bark, wood flour, nut shell flour, Collulose powder, residues from plant extractions, activated charcoal, ctc.,> Each for themselves or as mixtures with one another.
Die korngrösse der Trägerstoffe beträgt für Stäubemittel zweckmässig bis ca. 0,1 mm, für Streumittel ca. 0,075 mm bis 0,2 iwn und für Granulate 0,2 mm oder mehr. The grain size of the carrier is appropriate for dust up to approx. 0.1 mm, for grit approx. 0.075 mm up to 0.2 iwn and for Granules 0.2 mm or more.
Die Wirkstoffkonzentrationen in den festen Aufarbeitungsformen betragen 0,5 bis 80 %. The active ingredient concentrations in the solid work-up forms are 0.5 to 80%.
Diesen Gemischen können ferner den Wirkstoff stabilisierende Zusätze und/oder nichtionische, anionenaktive und kationenaktive Stoffe zugegeben werden, die beispielsweise die Haftfestigkeit der Wirkstoffe auf Pflanzen und Pflanzenteilen verbessern (llaft- und Klebemittel) und/oder eine besse-le Benetzbarkeit (Netzmittel) sowie Dispergierbarkeit (Dispergatoren) gewährleisten. Als Klebemitüel kommen beusoueksweuse die folgenden in Frage: Olein-Kalk-Mischung, Cellulosederivate *Netgtkcekkykisem Carboxymethylcellulose) , Gtdrixtäthylglykoläther von Mono- und Dialkyl -phenolen mit 5-15 Aethyleno';idresten pro Molekül und 3-9 Kohlenstoffatomen im Alkylrest Ligninsulfonsäure, deren Alkali- und Erdalkalisalze, Polyäthylenglykoläther (Carbowaxe), Fettalkoholpolyäthylenglykoläther mit 5-20 Aethylenoxidresten pro Molekül und 8-18 Kohlenstoffatomen im Fettalkoholteil, Kondensationsprodukte von Aethylenoxid, Propylenoxid, Polyvinylpyrrolidone, Polyvinylalkohole, Kondensationsprodukte von Harnstoff-Formaldehyd sowie Latex-Produkte. These mixtures can also contain additives stabilizing the active ingredient and / or non-ionic, anion-active and cation-active substances are added, For example, the adhesive strength of the active ingredients on plants and plant parts improve (air release agent and adhesive) and / or better wettability (wetting agent) and ensure dispersibility (dispersants). Beusoueksweuse are used as adhesives the following in question: olein-lime mixture, cellulose derivatives * Netgtkcekkykisem Carboxymethyl cellulose), diethyl glycol ether of mono- and dialkyl phenols with 5-15 ethyleneo '; id radicals per molecule and 3-9 carbon atoms in the alkyl radical Ligninsulphonic acid, its alkali and alkaline earth salts, polyethylene glycol ethers (Carbowaxe), Fatty alcohol polyethylene glycol ether with 5-20 ethylene oxide residues per molecule and 8-18 Carbon atoms in the fatty alcohol part, condensation products of ethylene oxide, propylene oxide, Polyvinylpyrrolidones, polyvinyl alcohols, condensation products of urea-formaldehyde as well as latex products.
In Wasser dispergierbare Wirkstoffkonzentrate, d.h. Spritzpulver (wettable powder), Pasten und Emulsionskonzentrate stellen Mittel dar, die mit Wasser auf jede gewünschte Konzentration verdünnt werden können. Sie bestehen aus Wirkstoff, Trägerstoff, gegebenenfalls den Wirkstoff stabilisierenden Zusätzen, oberflächenaktiven Substanzen und Antischaummitteln und gegebenenfalls Lösungsmitteln. Die Wirkstoff@onzentration in diesen Mitteln beträgt 5-80%. Active ingredient concentrates dispersible in water, i.e. wettable powders (wettable powder), pastes and emulsion concentrates are agents that work with water can be diluted to any desired concentration. They consist of active ingredient, Carrier, optionally additives stabilizing the active ingredient, surface-active Substances and antifoam agents and optionally solvents. The active ingredient concentration in these funds is 5-80%.
Die Spritzpulver (wettable powder) und Pasten werden erhalten, indem man die Wirkstoffe mit Dispergiermitteln und pulverförmigen Trägerstoffen in geeigneten Vorrichtungen bis zur Homogenität vermischt und vermahlt. Als Trägerstoffe können beispielsweise die vorstehend fUr die festen Aufarbeitungsformen erwähnten in Frage. In manchen. Fällen ist cs vorteilhaft Mischungen verschiedener Trägerstoffe zu verwenden. Als Dispergatoren können beispielsweise verwendet werden: Kondensationsprodukte von sulfonier tem Naphthalin und sulfonierten Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalin -sulfonsäuren mit Phenol und Formaldehyd sowie Alkali-, Ammonium- und Erdalkalisalze von Ligninsulfonsäure, weiter Alkylarylsulfonate, Alkali- und Erdalkalimetallsalze der Dibutylnaphthalinsulfonsäure, Fettalkoholsulfate, wie Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole und Salze von sulfatiertem Fettalkoholglykoläther, das Natriumsa]- von Oleylmethyltaurid, ditertiäre Acetylenglykohle Dialk)lldilaurylan;moniumchlorid und fettsaure Alkali-und Erdalkalisalze. The wettable powders and pastes are obtained by the active ingredients with dispersants and powdery carriers in suitable Devices mixed and ground to homogeneity. Can be used as a carrier for example those mentioned above for the solid preparation forms in question. In some. In some cases, it is advantageous to use mixtures of different carriers. Examples of dispersants that can be used are: Condensation products of sulfonated naphthalene and sulfonated naphthalene derivatives with formaldehyde, Condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde as well as alkali, ammonium and alkaline earth salts of ligninsulphonic acid, further alkylarylsulfonates, alkali and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, Fatty alcohol sulfates, such as salts of sulfated hexadecanols, heptadecanols, octadecanols and salts of sulfated fatty alcohol glycol ether, sodium sa] - of oleyl methyl tauride, ditertiary acetylene glycol dialk) lldilaurylan; monium chloride and fatty acid alkali and Alkaline earth salts.
Als Antischaummittel kommen zum Beispiel Silicone in Frage. Silicones, for example, can be used as antifoam agents.
Die Wirkstoffe werden mit den oben aufgeführten Zusätzen so vermischt, vermahlen, gesiebt und passiert, dass bei den Spritzpulvern der feste Anteil eine Korngrösse von 0,02 bis 0,04 r'n und bei den @ Pasten von 0,03 null nicht überschreitet. Zur herstellung von Emulsionskonzentraten und pasten werden Dispergiermittel, wie sie in den vorangehenden Abschnitten aufgeführt wurden, organische Lösungsmittel und Wasser verwendet. Als Lösungsmittel kommen beispielsweise die folgenden in Frages Alkohole, Bensol, Xylol Toluol, Dimethylsulfoxyd und im Bereich von 120 bis 350° siedende Mineralölfraktionen. Die Lösungsmittel müssen praktisch geruchlos, nicht phytotoxisch, den Wirkstoffen gegen-Uber inert und dUrfen nicht leicht brennbar sein. The active ingredients are mixed with the additives listed above in such a way that ground, sifted and happens that the solid part of the wettable powders is a Grain size of 0.02 to 0.04 r'n and in the case of the @ pastes of 0.03 does not exceed zero. For the production of emulsion concentrates and pastes, dispersants such as they are listed in the previous sections, organic solvents and water used. For example, the following can be used as solvents Alcohols, benzene, xylene Toluene, dimethyl sulfoxide and in the area Mineral oil fractions boiling from 120 to 350 °. The solvents need to be practical odorless, not phytotoxic, inert to the active ingredients and must not be easily flammable.
Ferner können die erfindungsgemässen Mittel in Form von Lösungen angewendet werden. Hierzu wird der Wirkstoff bzw. werden werden mehrere Wirlssto:.fe der allgemeinen Formel I in geeigneten organischen Lösungsmitteln, Lösungsmittelgemischen oder Wasser gelöst. Als organische LUsungsmittel können aliphatische und aromatische Kohlenwasserstoffe, deren chlorierte Derivate, Alkylnaphthaline, Mineralöle allein oder als Mischung untereinander verwendet werden. Die Lösungen sollen die Wirkstoffe in einem Konzentrationsbereich von 1 bis 20 % enthalten. The agents according to the invention can also be used in the form of solutions be applied. For this purpose, the active ingredient or will be several active ingredients: .fe of the general formula I in suitable organic solvents, solvent mixtures or dissolved in water. Aliphatic and aromatic solvents can be used as organic solvents Hydrocarbons, their chlorinated derivatives, alkylnaphthalenes, mineral oils alone or used as a mixture with one another. The solutions are supposed to be the active ingredients contained in a concentration range of 1 to 20%.
Den beschriebenen erfindungsgemässen Mitteln lassen sich andere biozide Wirkstoffe oder Mittel beimischen.So können die neuen Mittel ausser den genannten Verbindungen der allgemeinen Formel I zum Beispiel Insektizide, Fungizide, Bakterizide, Fungis tatika, Bakteriostatika oder Nematozide zur Verbreiterung des Wirkungsspektrums enthalten. Die erfindungsgemässen Mittel können ferner noch Pflanzelldüllger, Spurenelemente usw. enthalten. Other biocides can be used with the described compositions according to the invention Mix in active ingredients or agents, so the new agents can be used in addition to the ones mentioned Compounds of general formula I, for example insecticides, fungicides, bactericides, Fungis tatika, bacteriostatics or nematocides to broaden the spectrum of activity contain. The agents according to the invention can also contain vegetable manure, trace elements etc. included.
Im folgenden werden Aufarbeitungsformen der neuen Triazine beschrieben. Teile bedeuten Gewichtsteile. . Work-up forms of the new triazines are described below. Parts mean parts by weight. .
Granulat Zur Herstellung eines 5%igen Granulates werden die folgenden Stoffe verwendet: 5 Teile 2-Methoxy-4-isopropylamino-6-(trimethylsilylamino)-s-triazin, 0,25 Teile Epichlorhydrin, 0,25 Teile Cetylpolyglykoläther, 3,50 Teile Polyäthylenglykol, 91 Teile Kaolin (Korngrösse 0,3 bis 0,8 mm).Granules The following are used to produce 5% granules Substances used: 5 parts of 2-methoxy-4-isopropylamino-6- (trimethylsilylamino) -s-triazine, 0.25 part of epichlorohydrin, 0.25 part of cetyl polyglycol ether, 3.50 parts of polyethylene glycol, 91 parts of kaolin (grain size 0.3 to 0.8 mm).
Die Aktivsubstanz wird mit Epichlorhydrin vermischt und in 6 Teilen Aceton gelöst, hierauf wird Polyäthylenglykol und Cetylpolyglykoläther zugesetzt. Die so erhaltene Lösung wird auf Kaolin aufgespruht und anschliessend im Vakuum verdampft. The active ingredient is mixed with epichlorohydrin and divided into 6 parts Dissolved acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution obtained in this way is sprayed onto kaolin and then in vacuo evaporates.
Spritzpulver Zur Herstellung eines a) 50%igen, b) 25%igen und c) 10%igen Spritzpulvers werden folgende Bestandteile verwendet: a) 50 Teile 2-Chlor-4-isopropylamino-6-(trimethylsilylamino)-s-triazin, 5 Teile Natriumdibutylnaphthylsulfonat, 3 Teile Naphthalinsulfonsäuren-Phenolsulfonsäuren-Formaldehyd-Kondensat 3:2:1, 20 Teile Kaolin, 22 Teile Champagne-Kreide; b) 25 Teile 2-Methylthio-4-äthylamino-6-(trimethylsilylamino)-s-triazin, 5 Teile Oleylmethyltaurid-Natrium-Salz, 2,5 Teile Naphthalinsulfonsäuren-Formaldehyd-Kondensat, 0,5 Teile Carboxymethylcellulose, 5 Teile neutrales Kalium-Aluminiumsilikat, 62 Teile Kaolin; c) 10 Teile 2-Methylthio-4-n-propylamino-6- (trimethylsilylamino)-s-triazin, 3 Teile Gemisch der Natriumsalze von gesättigten Fettalkoholsulfaten, 5 Teile Naphthalinsulfonsäuren-Formaldehyd-Kondensat, 82 Teile Kaolin.Spray powder For the production of a) 50%, b) 25% and c) 10% The following ingredients are used: a) 50 parts of 2-chloro-4-isopropylamino-6- (trimethylsilylamino) -s-triazine, 5 parts of sodium dibutylnaphthylsulphonate, 3 parts of naphthalenesulphonic acids-phenolsulphonic acids-formaldehyde condensate 3: 2: 1, 20 parts of kaolin, 22 parts of Champagne chalk; b) 25 parts of 2-methylthio-4-ethylamino-6- (trimethylsilylamino) -s-triazine, 5 parts of oleylmethyltauride sodium salt, 2.5 parts of naphthalenesulfonic acid-formaldehyde condensate, 0.5 parts carboxymethyl cellulose, 5 parts neutral potassium aluminum silicate, 62 Parts of kaolin; c) 10 parts of 2-methylthio-4-n-propylamino-6- (trimethylsilylamino) -s-triazine, 3 parts mixture of the sodium salts of saturated fatty alcohol sulfates, 5 parts naphthalenesulfonic acid-formaldehyde condensate, 82 parts of kaolin.
Der angegebene Wirkstoff wird auf die entsprechenden Trägerstoffe (Kaolin und Kreide) aufgezogen und anschliessend vermischt und vermahlen. Man erhält Spritzpulver von vorzüglicher Benetzbarkeit und Schwebefähigkeit. Aus solchen Spritzpulvern können durch VerdUnnen niit Wasser Suspensionen jeder gewtlnschten Wirkstoffkonzentration erhalten werden. Derartige Suspensionen werden zur Bekämpfung von Unkräutern und Ungräsern in Kulturpflanzungen verwendet. The specified active ingredient is applied to the appropriate carriers (Kaolin and chalk) drawn up and then mixed and ground. You get Wettable powder with excellent wettability and suspension properties. From such wettable powders By diluting with water, suspensions of any desired concentration of active substance can be created can be obtained. Such suspensions are used to control weeds and Weed grasses used in crops.
Paste Zur Herstellung einer 45%igen Paste werden folgende Stoffe verwendet: 45 Teile 2-Chlor-4-tert-butylamino-6-(trimethylsilylamino)-s-triazin, 5 Teile Natriumaluminiumsilikat, 14 Teile Cetylpolyglykoläther mit 8 Mol Aethylenoxid, 1 Teil Oleylpolyglykoläther mit 5 Mol Aethylenoxid, 2 Teile Spindelöl, 10 Teile Polyäthylenglykol, 23 Teile Wasser.Paste The following substances are used to produce a 45% paste: 45 parts of 2-chloro-4-tert-butylamino-6- (trimethylsilylamino) -s-triazine, 5 parts of sodium aluminum silicate, 14 parts of cetyl polyglycol ether with 8 moles of ethylene oxide, 1 part of oleyl polyglycol ether with 5 moles of ethylene oxide, 2 parts of spindle oil, 10 parts of polyethylene glycol, 23 parts Water.
Der Wirkstoff wird mit den Zuschlagstoffen in dazu geeigneten Geräten innig vermischt und vermahlen. Man erhält eine Paste, aus der sich durch Verdünnen mit Wasser Suspensionen jeder gewUnschten Konzentration herstellen lassen. Die Suspensionen eignen sich zur Behandlung von GemUsepflanzungen. The active ingredient is mixed with the additives in suitable devices intimately mixed and ground. A paste is obtained from which, by diluting it Have suspensions of any desired concentration made with water. The suspensions are suitable for treating vegetable plantations.
Emulsionskonzentrat Zur llerstellung eines 257igen Emulsionskonzentrates werden 25 Teile 2-Methylthio-4-isopropylamino-6-(trimethylsilylamino)-s-triazin, 5 Teile einer Mischung von Nonylphenolpolyoxyäthylen und Calcium-dodecylbenzolsulfonat, 70 Teile 3,5,5-Trimethyl-2-cyclohexen-l-on miteinander vermischt. Dieses Konzentrat kann mit Wasser zu Emulsionen auf geeignete Konzentrationen verdUnnt werden. Solche Emulsionen eignen sich zur Bekämpfung von Unkräutern in Kulturpflanzungen, wie z. B. Baumwolle, Mais, etc..Emulsion concentrate For the production of an emulsion concentrate 25 parts of 2-methylthio-4-isopropylamino-6- (trimethylsilylamino) -s-triazine, 5 parts of a mixture of nonylphenol polyoxyethylene and calcium dodecylbenzenesulfonate, 70 parts of 3,5,5-trimethyl-2-cyclohexen-l-one mixed with one another. This concentrate can be diluted to suitable concentrations with water to form emulsions. Such Emulsions are suitable for controlling weeds in crops, such as. B. cotton, corn, etc ..
Claims (6)
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CH258171 | 1971-02-23 |
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DE19722208329 Pending DE2208329A1 (en) | 1971-02-23 | 1972-02-22 | 2-substd-4-trialkylsilylamino-6-amino-s-triazines - - with herbicidal and plant growth regulating activity |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4330535A (en) | 1980-01-04 | 1982-05-18 | Basf Aktiengesellschaft | Fungicidal azolyl-silyl-glycol ethers, their use for combating fungi, and agents therefor |
WO2014161834A1 (en) * | 2013-04-05 | 2014-10-09 | Basf Se | Process for the silylation of 2-amino-1,3,5-triazines |
-
1972
- 1972-02-22 DE DE19722208329 patent/DE2208329A1/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4330535A (en) | 1980-01-04 | 1982-05-18 | Basf Aktiengesellschaft | Fungicidal azolyl-silyl-glycol ethers, their use for combating fungi, and agents therefor |
WO2014161834A1 (en) * | 2013-04-05 | 2014-10-09 | Basf Se | Process for the silylation of 2-amino-1,3,5-triazines |
US9309270B2 (en) | 2013-04-05 | 2016-04-12 | Basf Se | Process for the silylation of 2-amino-1,3,5-triazines |
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