EP0000940B1 - Gamma-azolyl alcohols and their use as plant growth regulators - Google Patents
Gamma-azolyl alcohols and their use as plant growth regulators Download PDFInfo
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- EP0000940B1 EP0000940B1 EP78100725A EP78100725A EP0000940B1 EP 0000940 B1 EP0000940 B1 EP 0000940B1 EP 78100725 A EP78100725 A EP 78100725A EP 78100725 A EP78100725 A EP 78100725A EP 0000940 B1 EP0000940 B1 EP 0000940B1
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- triazolyl
- dimethylpentan
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- azolyl
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Definitions
- the present invention relates to new valuable y-azolyl alcohols with good biological activity, agents for regulating plant growth which contain these compounds and methods for regulating plant growth with these compounds.
- Plant growth regulators can e.g. cause a reduction in length growth, induce germination or flowering, increase frost resistance, or promote or inhibit the formation of side shoots.
- y-azolyl alcohols have the general formula in which R 1 and R 2 are the same or different and are alkyl with up to 5 carbon atoms, cycloalkyl, furanyl, thiophenyl, pyridyl, naphthyl or phenyl, the phenyl radical being halogen, alkyl, alkoxy, alkenyloxy, hydroxy, nitro, Trifluoromethyl can be substituted and R 1 can also be biphenyl and Az means an imidazolyl, pyrazolyl, 1,2,4-triazolyl or a 1,2,3-triazole radical, show a very good plant growth-regulating activity.
- the y-azolyl alcohols according to the invention are very suitable for regulating growth in numerous plants, which is manifested in particular in a reduction in length growth. The effect is better than with known growth regulators.
- the effect is particularly evident in cereals, e.g. Wheat, rye, barley, rice and oats, but also for dicots (e.g. sunflowers, tomatoes, vines, cotton, rapeseed) and various ornamental plants, such as poinsettias and hibiscus.
- dicots e.g. sunflowers, tomatoes, vines, cotton, rapeseed
- various ornamental plants such as poinsettias and hibiscus.
- the treated plants accordingly have a lower growth; a darker leaf color can also be observed.
- the y-azolyl alcohols according to the invention can be obtained from the crop plants both via the soil, i.e. through the root, as well as by spraying over the leaf. Due to the high plant tolerance, the application rate can be varied widely; in general, however, applications of 0.25 to 12 kg / ha should be considered sufficient.
- R 1 means, for example, methyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, furfuryl, thiophenyl, naphthyl, biphenylyl, phenyl, p-tolyl, m- and p-methoxy-phenyl, p -Fluorophenyl, p-chlorophenyl or 2,4-dichlorophenyl.
- R 2 means, for example, tert-butyl, furfuryl, 2-methyl-furfuryl, thiophenyl, pyridyl, naphthyl, phenyl, p-tolyl, p-isopropyl-phenyl, o- and p-methoxy-phenyl, 2,3-dimethoxy- phenyl, o-hydroxyphenyl, p-chlorophenyl, m- and p-bromophenyl, 2,4-dichlorophenyl, 2,4-dibromophenyl or p-nitrophenyl.
- the starting materials of formula (II) can be prepared as follows.
- ⁇ - (1,2,4-triazol- (1)) - yl, ⁇ -imidazolyl and ⁇ -pyrazolyl ketones of the formula (II) are obtained if appropriately substituted ⁇ , ⁇ -unsaturated ketones are used with the desired azoles in the presence of solvent or diluent at temperatures between 20 and 80 ° C or if instead of ⁇ , ⁇ -unsaturated ketones the corresponding aldehydes and ketones in the presence of azoles and optionally in the presence of a basic catalyst and optionally in the presence of a Converts diluent. Regulation A
- a solution of 11 g (0.11 mol) of 3,3-dimethylbutan-2-one and 14 g (0.1 mol) of p-chlorobenzaldehyde in 120 ml of ethanol are mixed with 10 ml of 20% aqueous sodium hydroxide solution and 2 hours at 50 ° C stirred. After adding 13.8 g (0.2 mol) of 1,2,4-triazole, the mixture is stirred at 50 ° C. for a further 8 hours. The solvent is then distilled off and the remaining residue is partitioned between 300 ml of water and 300 ml of ether.
- the ethereal solution is dried over CaS0 4 , filtered off and gassed with dry hydrogen chloride at 5 to 10 °.
- ketones can be used as starting products, for example.
- the following example relates to the preparation of the y-azolyl alcohols according to the invention.
- the active compounds according to the invention are used e.g. in the form of directly sprayable solutions, powders, suspensions, including high-proof aqueous, oily or other suspensions, or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring.
- the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active substances according to the invention.
- mineral oil fractions of medium to high boiling points such as kerosene or diesel oil, also coal tar oils etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example loluene, xylene, Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alcohols (for example methanol, butanol), amines (for example ethanolamine, dimethylformamide) and water; Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g.
- natural stone powder e.g. kaolins, clays, talc, chalk
- synthetic stone powder e.g.
- Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, leachate and methyl cellulose.
- nonionic and anionic emulsifiers e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates
- dispersants such as lignin, leachate and methyl cellulose.
- the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- agents according to the invention can also be present in these application forms together with other active ingredients, e.g. Herbicides, insecticides, growth regulators and fungicides or even mixed with fertilizers.
- active ingredients e.g. Herbicides, insecticides, growth regulators and fungicides or even mixed with fertilizers.
- the active ingredients according to the invention are used in a favorable period of time, the exact determination of which depends on the geographical, climatic and vegetative conditions.
- Tests were carried out in the greenhouse to test the biological activity of the new compounds.
- the test plants were sown into plastic containers with a diameter of 12.5 cm using peat culture substrate which was sufficiently supplied with nutrients.
- the active compounds are applied in aqueous solution or dispersion in different amounts to the soil on the day of sowing.
- the substances were sprayed directly onto the surface of the floor.
- the plants treated with the agents according to the invention showed a significantly lower growth in length than the untreated control, which could be confirmed by subsequent length measurements.
- 100 plants from each treatment series were measured.
- active ingredient 5 20 parts by weight of active ingredient 5 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
- a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
- active ingredient 3 40 parts by weight of active ingredient 3 are intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid urea formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active ingredient.
- active ingredient 4 20 parts of active ingredient 4 are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.
Description
Die vorliegende Erfindung betrifft neue wertvolle y-Azolylalkohole mit guter biologischer Wirkung, Mittel zur Regulierung des Pflanzenwachstums, die diese Verbindungen enthalten, und Verfahren zur Regulierung des Pflanzenwachstums mit diesen Verbindungen.The present invention relates to new valuable y-azolyl alcohols with good biological activity, agents for regulating plant growth which contain these compounds and methods for regulating plant growth with these compounds.
Es ist bekannt, daß 2-Chloräthyl-trimethylammoniumchlorid (Chlorcholinchlorid, CCC) (J. Biol. Chem., 235,475 (1960) zur Beeinflussung des Pflanzenwachstums zu verwenden.It is known to use 2-chloroethyl-trimethylammonium chloride (chlorcholine chloride, CCC) (J. Biol. Chem., 235,475 (1960) to influence plant growth.
Pflanzenwachstumsregulatoren können z.B. eine Reduzierung des Längenwachstums verursachen, eine Keim- oder Blühinduktion auslösen, die Frostresistenz erhöhen, oder die Ausbildung von Seitentrieben fördern bzw. hemmen.Plant growth regulators can e.g. cause a reduction in length growth, induce germination or flowering, increase frost resistance, or promote or inhibit the formation of side shoots.
Von großem wirtschaftlichen Interesse ist besonders die Verhinderung des "Lagerns" von Getreide vor der Ernte durch Wachstumsregulatoren.Prevention of the "storage" of grain before harvesting by growth regulators is of particular economic interest.
Bei der Anwendung der bekannten Handelsprodukte als Mittel zur Regulierung des Pflanzenwachstums, z.B. auf Getreidearten, bei der ein gedrungener Wuchs zur Unterbindung des Lagerns erreicht werden soll, ist die Wirkung oft nicht ausreichend.When using the known commercial products as a means of regulating plant growth, e.g. the effect is often not sufficient on cereals in which a compact growth is to be prevented to prevent storage.
Es wurde gefunden, daß y-Azolylalkohole der allgemeinen Formel
Die erfindungsgemäßen y-Azolylalkohole eignen sich sehr gut bei zahlreichen Pflanzen zur Regulierung des Wachstums, was sich insbesondere in einer Reduzierung des Längenwachstums äußert. Die Wirkung ist besser als bei bekannten Wachstumsregulatoren.The y-azolyl alcohols according to the invention are very suitable for regulating growth in numerous plants, which is manifested in particular in a reduction in length growth. The effect is better than with known growth regulators.
Die Wirkung zeigt sich vor allem bei Getreide, z.B. Weizen, Roggen, Gerste, Reis und Hafer, aber auch bei Dikotylen (z.B. Sonnenblumen, Tomaten, Reben, Baumwolle, Raps) und verschiedenen Zierpflanzen, wie Poinsettien und Hibiskus. Die behandelten Pflanzen weisen demgemäß einen niedrigeren Wuchs auf; außerdem ist eine dunklere Blattfärbung zu beobachten.The effect is particularly evident in cereals, e.g. Wheat, rye, barley, rice and oats, but also for dicots (e.g. sunflowers, tomatoes, vines, cotton, rapeseed) and various ornamental plants, such as poinsettias and hibiscus. The treated plants accordingly have a lower growth; a darker leaf color can also be observed.
Die erfindungsgemäßen y-Azolylalkohole können den Kulturpflanzen sowohl über den Boden, d.h. durch die Wurzel, als auch durch Spritzung über das Blatt zugeführt werden. Infolge der hohen Pflanzenverträglichkeit kann die Aufwandmenge stark variiert werden; im allgemeinen sind aber Gaben von 0,25 bis 12 kg/ha als ausreichend zu betrachten.The y-azolyl alcohols according to the invention can be obtained from the crop plants both via the soil, i.e. through the root, as well as by spraying over the leaf. Due to the high plant tolerance, the application rate can be varied widely; in general, however, applications of 0.25 to 12 kg / ha should be considered sufficient.
R1 bedeutet beispielsweise Methyl, Isopropyl, n-Butyl, sek.-Butyl, iso-Butyl, tert.-Butyl, Furfuryl, Thiophenyl, Naphthyl, Biphenylyl, Phenyl, p-Tolyl, m- und p-Methoxy-phenyl, p-Fluorphenyl, p-Chlorphenyl oder 2,4-Dichlor-phenyl.R 1 means, for example, methyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, furfuryl, thiophenyl, naphthyl, biphenylyl, phenyl, p-tolyl, m- and p-methoxy-phenyl, p -Fluorophenyl, p-chlorophenyl or 2,4-dichlorophenyl.
R2 bedeutet beispielsweise tert.-Butyl, Furfuryl, 2-Methyl-furfuryl, Thiophenyl, Pyridyl, Naphthyl, Phenyl, p-Tolyl, p-Isopropyl-phenyl, o- und p-Methoxy-phenyl, 2,3-Dimethoxy-phenyl, o-Hydroxyphenyl, p-Chlorphenyl, m- und p-Bromphenyl, 2,4-Dichlorphenyl, 2,4-Dibromphenyl oder p-Nitrophenyl.R 2 means, for example, tert-butyl, furfuryl, 2-methyl-furfuryl, thiophenyl, pyridyl, naphthyl, phenyl, p-tolyl, p-isopropyl-phenyl, o- and p-methoxy-phenyl, 2,3-dimethoxy- phenyl, o-hydroxyphenyl, p-chlorophenyl, m- and p-bromophenyl, 2,4-dichlorophenyl, 2,4-dibromophenyl or p-nitrophenyl.
Die erfindungsgemäßen Verbindungen der Formel I sind neu und können in folgender Weise hergestellt werden. Man erhält sie beispielsweise, indem man ß-Azolylketone der Formel
- a) mit komplexen Hydriden, wie Natriumborhydrid in Gegenwart eines polaren Lösungsmittels, wie zum Beispiel Methanol oder mit Lithiumalanat in Tetrahydrofuran, bei Temperaturen zwischen 0°C und 30°C und anschließende Hydrolyse, z.B. mit wäßrigen Basen oder Säuren, oder
- b) mit Wasserstoff in Gegenwart eines Katalysators, wie Platin oder Raney-Nickel und in Gegenwart eines polaren Lösungsmittels, wie Methanol, Äthanol, Isopropanol, bei einer Temperatur zwischen 40 und 60°C und einem Druck zwischen 1 bis 100 bar, und
- c) mit Aluminiumisopropylat in Gegenwart eines inerten Lösungsmittels bei einer Temperatur zwischen 40 und 120°C und anschließender Hydrolyse, z.B. mit wäßriger Salzsäure.
- a) with complex hydrides, such as sodium borohydride in the presence of a polar solvent, such as methanol or with lithium alanate in tetrahydrofuran, at temperatures between 0 ° C and 30 ° C and subsequent hydrolysis, for example with aqueous bases or acids, or
- b) with hydrogen in the presence of a catalyst such as platinum or Raney nickel and in the presence of a polar solvent such as methanol, ethanol, isopropanol, at a temperature between 40 and 60 ° C and a pressure between 1 to 100 bar, and
- c) with aluminum isopropylate in the presence of an inert solvent at a temperature between 40 and 120 ° C and subsequent hydrolysis, for example with aqueous hydrochloric acid.
Die so erhaltenen Verbindungen der Formel (I) werden nach den üblichen Methoden isoliert und gegebenenfalls gereinigt.The compounds of formula (I) thus obtained are isolated by the customary methods and, if appropriate, purified.
Die Ausgangsstoffe der Formel (II) können wie folgt hergestellt werden.The starting materials of formula (II) can be prepared as follows.
Man erhält die β-(1,2,4-Triazol-(1))-yl-, β-Imidazolyl- und β-Pyrazolyl-ketone der Formel (II), wenn man entsprechend substituierte α,β-ungesättigte Ketone mit den gewünschten Azolen in Gegenwart von Lösungs- oder Verdünnungsmittel bei Temperaturen zwischen 20 und 80°C umsetzt oder wenn man anstatt von α,β-ungesättigten Ketonen die entsprechenden Aldehyde und Ketone in Gegenwart von Azolen und gegebenenfalls in Gegenwart eines basischen Katalysators und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt. Vorschrift AThe β- (1,2,4-triazol- (1)) - yl, β-imidazolyl and β-pyrazolyl ketones of the formula (II) are obtained if appropriately substituted α, β-unsaturated ketones are used with the desired azoles in the presence of solvent or diluent at temperatures between 20 and 80 ° C or if instead of α, β-unsaturated ketones the corresponding aldehydes and ketones in the presence of azoles and optionally in the presence of a basic catalyst and optionally in the presence of a Converts diluent. Regulation A
Eine Lösung von 11 g (0,11 Mol) 3,3-Dimethylbutan-2-on und 14 g (0,1 Mol) p-Chlorbenzaldehyd in 120 ml Äthanol werden mit 10 ml 20 prozentiger wäßriger Natronlauge versetzt und 2 Stunden bei 50°C gerührt. Nach Zugabe von 13,8 g (0,2 Mol) 1,2,4-Triazol wird das Gemisch weitere 8 Stunden bei 50°C nachgerührt. Danach wird das Lösungsmittel abdestilliert und der verbleibende Rückstand zwischen 300 ml Wasser und 300 ml Äther verteilt.A solution of 11 g (0.11 mol) of 3,3-dimethylbutan-2-one and 14 g (0.1 mol) of p-chlorobenzaldehyde in 120 ml of ethanol are mixed with 10 ml of 20% aqueous sodium hydroxide solution and 2 hours at 50 ° C stirred. After adding 13.8 g (0.2 mol) of 1,2,4-triazole, the mixture is stirred at 50 ° C. for a further 8 hours. The solvent is then distilled off and the remaining residue is partitioned between 300 ml of water and 300 ml of ether.
Die ätherische Lösung wird über CaS04 getrocknet, abfiltriert und mit trockenem Chlorwasserstoff bei 5 bis 10° begast.The ethereal solution is dried over CaS0 4 , filtered off and gassed with dry hydrogen chloride at 5 to 10 °.
Man erhält 24,3 g (74% d. Th.) Hydrochlorid des 1-[1,2,4-Triazolyl-(1)]-1-(4'-chlor-phenyl)-4,4-dimethyl-pentan-3-on als weiße Kristalle vom Schmelzpunkt 139-141 °C.24.3 g (74% of theory) of hydrochloride of 1- [1,2,4-triazolyl- (1)] -1- (4'-chlorophenyl) -4,4-dimethylpentane are obtained -3-one as white crystals with a melting point of 139-141 ° C.
Folgende Ketone können beispielsweise als Ausgangsprodukte verwendet werden.
Das folgende Beispiel betrifft die Herstellung der erfindungsgemäßen y-Azolylalkohole.The following example relates to the preparation of the y-azolyl alcohols according to the invention.
In eine Lösung von 29,1 g 1-[1,2,4-Triazolyl-(1)]-1-(4'-chlorphenyl)-4,4-dimethyl-pentan-3-on in 300 ml Methanol werden unter Rühren und Eiskühlung bei 3 bis 8°C portionsweise 5,9 g Natriumborohydrid eingetragen. Nach 8-stündigem Rühren bei Raumtemperatur wird das Gemisch eingeengt. Der Rückstand wird mit 150 ml 4 prozentiger Natronlauge 1 Stunde gerührt und mit 250 ml Methylenchlorid extrahiert. Die organische Schicht wird über Na2S04 getrocknet und im Vakuum eingeengt. Der verbleibende feste, farblose Rückstand wird mit 40 ml Petroläther gewaschen und abgesaugt.In a solution of 29.1 g of 1- [1,2,4-triazolyl- (1)] - 1- (4'-chlorophenyl) -4,4-dimethyl-pentan-3-one in 300 ml of methanol Stirring and ice cooling in portions at 3 to 8 ° C 5.9 g of sodium borohydride. After stirring for 8 hours at room temperature, the mixture is concentrated. The residue is stirred with 150 ml of 4 percent sodium hydroxide solution for 1 hour and extracted with 250 ml of methylene chloride. The organic layer is dried over Na 2 S0 4 and concentrated in vacuo. The remaining solid, colorless residue is washed with 40 ml of petroleum ether and suction filtered.
Man erhält 26,1 g (89% d. Th.) 1-[1,2,4-Triazolyl-(1)]-1-(4'-chlor-phenyl)-4,4-dimethyl-pentan-3-ol vom Schmelzpunkt 104-106°C.26.1 g (89% of theory) of 1- [1,2,4-triazolyl- (1)] - 1- (4'-chlorophenyl) -4,4-dimethyl-pentane-3 are obtained -ol melting point 104-106 ° C.
1 b)1 b)
' 29,1 g 1-[1,2,4-Triazolyl-(1)]-1-(4'-chlorphenyl)-4,4-dimethylpentan-3-on werden in 100 ml wasserfreiem Äther gelöst. Diese Lösung wird zu einer Suspension von 5,7 g Lithiumalanat in 200 ml wasserfreiem Äther langsam hinzugetropft. Das Gemisch wird drei Stunden unter Rückfluß erhitzt und anschließend unter Eiskühlung tropfenweise mit 150 ml Eiswasser versetzt. Danach wird das Gemisch noch mit 200 ml 20 prozentiger (Gewichtsprozent) wäßriger Natronlauge gerührt und mit je 150 ml Äther dreimal extrahiert. Die organische Phase wird über Na2S04 getrocknet und im Vakuum eingeengt. Der teilweise kristallisierte Niederschlag wird mit Petroläther verrührt und gewaschen.'29.1 g of 1- [1,2,4-triazolyl- (1)] - 1- (4'-chlorophenyl) -4,4-dimethylpentan-3-one are dissolved in 100 ml of anhydrous ether. This solution is slowly added dropwise to a suspension of 5.7 g of lithium alanate in 200 ml of anhydrous ether. The mixture is heated under reflux for three hours and then 150 ml of ice water are added dropwise with ice cooling. The mixture is then stirred with 200 ml of 20 percent (weight percent) aqueous sodium hydroxide solution and extracted three times with 150 ml of ether. The organic phase is dried over Na 2 S0 4 and concentrated in vacuo. The partially crystallized precipitate is stirred with petroleum ether and washed.
Man erhält 24,9 g (85% d. Th.) 1-[1,2,4-T-riazolyl-(1)]-1-(4'-chlor-phenyl)-4,4-dimethyl-pentan-3-ol vom Schmelzpunkt 104-1060C.24.9 g (85% of theory) of 1- [1,2,4-T-riazolyl- (1)] - 1- (4'-chlorophenyl) -4,4-dimethylpentane are obtained -3-ol with melting point 104-106 0 C.
In entsprechender Weise können die in der folgenden Tabelle 2 aufgeführten Verbindungen hergestellt werden.
Die Anwendung der erfindungsgemäßen Wirkstoffe erfolgt z.B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen, auch hochprozentige wäßrige, ölige oder sonstige Suspensionen, oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln, Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsmäßen Wirkstoffe gewährleisten.The active compounds according to the invention are used e.g. in the form of directly sprayable solutions, powders, suspensions, including high-proof aqueous, oily or other suspensions, or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active substances according to the invention.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten und Öldispersionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkte, wie Kerosin oder Dieselöl, ferner Kohlenteeröle usw., sowie Öle pflanzlischen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, zum Beispiel Loluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Alkohole (z.B. Methanol, Butanol), Amine (z.B. Äthanolamin, Dimethylformamid) und Wasser; Trägerstoffe wie natürliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate); Emulgiermittel, wie nichtionogene und anionische Emulgatoren (z.B. Polyoxyäthylen-Fettalkohol-Äther, Alkylsulfonate und Arylsulfonate) und Dispergiermittel, wie Lignin, Sulfitablaugen und Methylcellulose.For the production of directly sprayable solutions, emulsions, pastes and oil dispersions, mineral oil fractions of medium to high boiling points, such as kerosene or diesel oil, also coal tar oils etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example loluene, xylene, Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alcohols (for example methanol, butanol), amines (for example ethanolamine, dimethylformamide) and water; Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, leachate and methyl cellulose.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90%.The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
Die erfindungsgemäßen Mittel können in diesen Aufwendungsformen auch zusammen mit anderen Wirkstoffen vorliegen, z.B. Herbiziden, Insektiziden, Wachstumsregulatoren und Fungiziden oder auch mit Düngemittel vermischt werden.The agents according to the invention can also be present in these application forms together with other active ingredients, e.g. Herbicides, insecticides, growth regulators and fungicides or even mixed with fertilizers.
Für die Anwendungszeit gilt, daß die Anwendung der erfindungsgemäßen Wirkstoffe in einem günstigen Zeitraum vorgenommen wird, dessen genaue Feststellung sich nach den geographischen, klimatischen und vegetativen Gegebenheiten richten.For the time of use, the active ingredients according to the invention are used in a favorable period of time, the exact determination of which depends on the geographical, climatic and vegetative conditions.
In den folgenden Beispielen wird die Wirkung der erfindungsgemäßen Stoffe als Wachstumsregulatoren dargestellt, ohne die Möglichkeit weiterer Anwendungen als Wachstumsregulatoren auszuschließen.The effect of the substances according to the invention as growth regulators is shown in the following examples, without excluding the possibility of further applications as growth regulators.
Zur Prüfung der biologischen Wirksamkeit der neuen Verbindungen wurden im Gewächshaus Versuche durchgeführt. Dabei wurden die Testpflanzen unter Verwendung von Torfkultursubstrat, welches ausreichend mit Nährstoffen versorgt war, in Kunststoffgefäße mit einem Durchmesser von 12,5 cm eingesät. Die Anwendung der Wirkstoffe erfolgt in wäßriger Lösung oder Dispersion in unterschiedlichen Aufwandmengen auf den Boden am Tage der Einsaat. Die Substanzen wurden dabei direkt auf die Bodenoberfläche gespritzt. Während der Wachstumszeit von 18 Tagen zeigten die mit den erfindungsgemäßen Mitteln behandelten Pflanzen gegenüber der unbehandelten Kontrolle ein deutlich geringeres Längenwachstum, was durch anschliessende Längenmessungen bestätigt werden konnte. Hierbei wurden von jeder Behandlungsreihe 100 Pflanzen gemessen.Tests were carried out in the greenhouse to test the biological activity of the new compounds. The test plants were sown into plastic containers with a diameter of 12.5 cm using peat culture substrate which was sufficiently supplied with nutrients. The active compounds are applied in aqueous solution or dispersion in different amounts to the soil on the day of sowing. The substances were sprayed directly onto the surface of the floor. During the growth period of 18 days, the plants treated with the agents according to the invention showed a significantly lower growth in length than the untreated control, which could be confirmed by subsequent length measurements. Here, 100 plants from each treatment series were measured.
Der bekannte Wirkstoff 2-Chloräthyl-trimethyl-ammoniumchlorid (A) zeigte eine schlechtere Wirkung (Ergebnisse s. Tabelle 3-5).
Man vermischt 90 Gewichtsteile der Verbindung 3 mit 10 Gewichtsteilen N-Methyl-a-pyrrolidon und erhält eine Lösung, die zur Anwendung in Form kleinster Tropfen geeignet ist.90 parts by weight of compound 3 are mixed with 10 parts by weight of N-methyl-a-pyrrolidone, and a solution is obtained which is suitable for use in the form of minute drops.
20 Gewichsteile der Verbindung 4 werden in einer Mischung gelöst, die aus 80 Gewichsteilen Xylol, 10 Gewichsteilen des Anlagerungsproduktes von 8 bis 10 Mol Äthylenoxid an 1 Mol Ölsäure-N-mono-äthanolamid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.20 parts by weight of compound 4 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-mono-ethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 Moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
20 Gewichtsteile der Verbindung 3 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon, 30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlagerungsproduktes von 7 Mol Äthylenoxid an 1 Mol Isooctylphenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.20 parts by weight of compound 3 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
20 Gewichtsteile der Verbindung 4 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanol, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.20 parts by weight of compound 4 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 Parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil are present. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
20 Gewichtsteile des Wirkstoffs 5 werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutylnaphthalin-a-sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermahlen. Durch feines Verteilen der Mischung in 20 000 Gewichtsteilen Wasser erhält man eine Spritzbrühe, die 0,1 Gewichtsprozent des.Wirkstoffs enthält.20 parts by weight of active ingredient 5 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
3 Gewichtsteile der Verbindung 3 werden mit 97 Gewichtsteilen feinteiliges Kaolin innig vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gewichtsprozent des Wirkstoffs enthält.3 parts by weight of compound 3 are intimately mixed with 97 parts by weight of finely divided kaolin. In this way a dust is obtained which contains 3 percent by weight of the active ingredient.
30 Gewichtsteile der Verbindung 4 werden mit einer Mischung aus 92 Gewichtsteilen pulverförmigem Kieselsäuregel und 8 Gewichtsteilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde, innig vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit.30 parts by weight of compound 4 are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. In this way, a preparation of the active ingredient with good adhesiveness is obtained.
40 Gewichtsteile des Wirkstoffs 3 werden mit 10 Teilen Natriumsalz eines Phenolsulfonsäureharnstoff-formaldehyd-kondensats, 2 Teilen Kieselgel und 48 Teilen Wasser innig vermischt. Man erhält eine stabile wäßrige Dispersion. Durch Verdünnen mit 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,04 Gewichtsprozent Wirkstoff enthält.40 parts by weight of active ingredient 3 are intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid urea formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active ingredient.
20 Teile des Wirkstoffs 4 werden mit 2 Teilen Calciumsalz der Dodecylbenzolsulfonsäure, 8Teilen Fettalkohol-polyglykoläther, 2 Teile Natriumsalz eines Phenolsulfonsäure-harnstoff-formaldehydkondensats und 68 Teile eines paraffinischen Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion.20 parts of active ingredient 4 are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.
Claims (11)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772738725 DE2738725A1 (en) | 1977-08-27 | 1977-08-27 | AZOLYL ALCOHOLS |
| DE2738725 | 1977-08-27 | ||
| DE19772739352 DE2739352A1 (en) | 1977-08-27 | 1977-09-01 | MEANS OF REGULATING PLANT GROWTH |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0000940A2 EP0000940A2 (en) | 1979-03-21 |
| EP0000940A3 EP0000940A3 (en) | 1979-03-21 |
| EP0000940B1 true EP0000940B1 (en) | 1980-08-06 |
Family
ID=25772627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100725A Expired EP0000940B1 (en) | 1977-08-27 | 1978-08-23 | Gamma-azolyl alcohols and their use as plant growth regulators |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4328028A (en) |
| EP (1) | EP0000940B1 (en) |
| JP (2) | JPS5444026A (en) |
| AT (2) | AT359096B (en) |
| BE (1) | BE870081A (en) |
| CA (2) | CA1111429A (en) |
| DE (2) | DE2738725A1 (en) |
| FR (1) | FR2401611A1 (en) |
| GB (1) | GB2003848B (en) |
| NL (1) | NL7808961A (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2842801A1 (en) * | 1978-09-30 | 1980-04-10 | Basf Ag | BETA TRIAZOLYLOXIME |
| US4293561A (en) * | 1979-03-09 | 1981-10-06 | Syntex (U.S.A.) Inc. | 1-(Naphthyl-n-propyl)imidazole derivatives |
| US4554007A (en) * | 1979-03-20 | 1985-11-19 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
| DE2920437A1 (en) * | 1979-05-19 | 1980-11-27 | Bayer Ag | GEOMETRIC ISOMERS OF 4,4-DIMETHYL-1-PHENYL-2- (1,2,4-TRIAZOL-1-YL) -1-PENTEN-3-OLEN, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MEDICINAL PRODUCT |
| DE2921168A1 (en) * | 1979-05-25 | 1980-12-11 | Basf Ag | TRIAZOLYL DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF AND THEIR CONTAINERS FOR INFLUENCING PLANT GROWTH |
| DE2925687A1 (en) * | 1979-06-26 | 1981-01-22 | Basf Ag | TRIAZOLYL GLYCOLETHER CONTAINERS FOR REGULATING PLANT GROWTH |
| CH647513A5 (en) * | 1979-11-13 | 1985-01-31 | Sandoz Ag | TRIAZOLE DERIVATIVES, THEIR PRODUCTION AND USE. |
| DE2948206A1 (en) | 1979-11-30 | 1981-06-25 | Basf Ag, 6700 Ludwigshafen | FUNGICIDE (GAMMA) AZOLYL COMPOUNDS, THEIR PRODUCTION AND USE |
| DE3011258A1 (en) * | 1980-03-24 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | FUNGICIDAL AGENT, CONTAINING TRIAZOLYL DERIVATIVES AND METHOD FOR CONTROLLING FUNGI WITH YOU |
| DE3019049A1 (en) * | 1980-05-19 | 1981-12-03 | Basf Ag, 6700 Ludwigshafen | NEW AZOLES |
| DE3025879A1 (en) * | 1980-07-09 | 1982-02-11 | Basf Ag, 6700 Ludwigshafen | 1,3-DIOXAN-5-YL-ALKYLTRIAZOLE, THEIR PRODUCTION, THEIR USE FOR REGULATING THE PLANT GROWTH AND MEANS THEREFOR |
| DE3026140A1 (en) * | 1980-07-10 | 1982-02-18 | Basf Ag, 6700 Ludwigshafen | 1,3-DIOXAN-5-YL-ALKENYLTRIAZOLE, THEIR PRODUCTION, THEIR USE FOR REGULATING THE PLANT GROWTH AND MEANS THEREFOR |
| DE3215360A1 (en) * | 1982-04-24 | 1983-10-27 | Basf Ag, 6700 Ludwigshafen | BISAZOLYL COMPOUNDS, THEIR PRODUCTION, THEIR USE FOR REGULATING THE PLANT GROWTH AND MEANS THEREFOR |
| US4510148A (en) * | 1982-06-12 | 1985-04-09 | Pfizer Inc. | 2-Heterocyclic-1,3-bis(1H-1,2,4-triazol-1-yl)-propan-2-ols as antifungal agents |
| DE3233145A1 (en) * | 1982-09-07 | 1984-03-08 | Basf Ag, 6700 Ludwigshafen | NEOPENTYL-PHENETHYLTRIAZOLE, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM |
| DE3511922A1 (en) | 1985-04-01 | 1986-10-09 | Basf Ag, 6700 Ludwigshafen | AZOLE COMPOUNDS, METHOD FOR THEIR PRODUCTION AND MEANS FOR REGULATING PLANT GROWTH |
| DE3515309A1 (en) | 1985-04-27 | 1986-10-30 | Basf Ag, 6700 Ludwigshafen | 1,3-DIOXAN-5-YL-ALKYLTRIAZOLE, THEIR PRODUCTION, THEIR USE FOR REGULATING THE PLANT GROWTH AND MEANS THEREFOR |
| JPH034070A (en) * | 1989-06-01 | 1991-01-10 | Minolta Camera Co Ltd | Waterproof mechanism |
| CA2072892A1 (en) * | 1990-11-02 | 1992-05-03 | Motonobu Furuta | Thermoplastic resin composition |
| JP2700510B2 (en) * | 1991-05-17 | 1998-01-21 | 明治製菓株式会社 | Plant growth regulator and method for enhancing stress resistance of plant |
| US6156705A (en) * | 1997-12-04 | 2000-12-05 | Henkel Corporation | Use of fatty alcohol polyalkoxy alkyl ethers in agricultural formulations |
| KR102386124B1 (en) * | 2015-10-02 | 2022-04-14 | 삼성전자주식회사 | Polymer composition, method for producing polymer composition, electronic apparatus and method for producing electronic apparatus |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1569267A (en) * | 1975-12-16 | 1980-06-11 | Ici Ltd | Substituted propiophenones and herbicidal and fungicidal compositions containing them |
| DE2624529A1 (en) * | 1976-06-01 | 1977-12-22 | Bayer Ag | AMINOMETHYLAZOLE DERIVATIVES, THE PROCESS FOR THEIR PRODUCTION AND THEIR USE AS FUNGICIDES AND FOR THE REGULATION OF PLANT GROWTH |
| NZ184268A (en) * | 1976-06-08 | 1979-03-16 | Ici Ltd | 1,2,4-triazd-1-yl-alkone-diones derivatives and fungicidal and plant growth regulating compositions |
| DE2634511A1 (en) * | 1976-07-31 | 1978-02-02 | Basf Ag | BETA-AZOLYL KETONE |
| DE2656728A1 (en) | 1976-12-15 | 1978-06-29 | Basf Ag | Beta-imidazolyl-ketone systemic fungicides - useful for protecting cereal, cucumbers, grapes, apples and roses |
| US4181518A (en) * | 1976-12-24 | 1980-01-01 | Imperial Chemical Industries Limited | Method of regulating plant growth using triazole and imidazole compounds |
| DE2706670A1 (en) * | 1977-02-17 | 1978-08-24 | Basf Ag | Metal complexes of beta-triazolyl or imidazolyl ketone cpds. - useful as fungicides, e.g. against cereal mildews |
| DE2706838A1 (en) * | 1977-02-17 | 1978-08-24 | Bayer Ag | AGENTS FOR REGULATING PLANT GROWTH |
| GB1601453A (en) * | 1977-05-05 | 1981-10-28 | Ici Ltd | Triazole and imidazole derivatives useful in agriculture |
-
1977
- 1977-08-27 DE DE19772738725 patent/DE2738725A1/en not_active Withdrawn
- 1977-09-01 DE DE19772739352 patent/DE2739352A1/en not_active Withdrawn
-
1978
- 1978-08-22 CA CA309,850A patent/CA1111429A/en not_active Expired
- 1978-08-22 JP JP10151278A patent/JPS5444026A/en active Pending
- 1978-08-23 EP EP78100725A patent/EP0000940B1/en not_active Expired
- 1978-08-25 AT AT621378A patent/AT359096B/en not_active IP Right Cessation
- 1978-08-25 US US05/936,741 patent/US4328028A/en not_active Expired - Lifetime
- 1978-08-28 JP JP10397878A patent/JPS5449328A/en active Pending
- 1978-08-30 BE BE190160A patent/BE870081A/en not_active IP Right Cessation
- 1978-08-30 GB GB7834993A patent/GB2003848B/en not_active Expired
- 1978-08-31 CA CA310,390A patent/CA1111430A/en not_active Expired
- 1978-08-31 NL NL7808961A patent/NL7808961A/en not_active Application Discontinuation
- 1978-08-31 AT AT632478A patent/AT358079B/en active
- 1978-08-31 FR FR7825190A patent/FR2401611A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2401611B1 (en) | 1983-09-09 |
| GB2003848A (en) | 1979-03-21 |
| DE2738725A1 (en) | 1979-03-08 |
| EP0000940A2 (en) | 1979-03-21 |
| JPS5444026A (en) | 1979-04-07 |
| CA1111429A (en) | 1981-10-27 |
| AT359096B (en) | 1980-10-27 |
| ATA632478A (en) | 1980-01-15 |
| FR2401611A1 (en) | 1979-03-30 |
| AT358079B (en) | 1980-08-25 |
| ATA621378A (en) | 1980-03-15 |
| CA1111430A (en) | 1981-10-27 |
| US4328028A (en) | 1982-05-04 |
| JPS5449328A (en) | 1979-04-18 |
| EP0000940A3 (en) | 1979-03-21 |
| DE2739352A1 (en) | 1979-03-15 |
| GB2003848B (en) | 1982-03-17 |
| BE870081A (en) | 1979-02-28 |
| NL7808961A (en) | 1979-03-05 |
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