DE2656747A1 - MORPHOLINE DERIVATIVES - Google Patents
MORPHOLINE DERIVATIVESInfo
- Publication number
- DE2656747A1 DE2656747A1 DE19762656747 DE2656747A DE2656747A1 DE 2656747 A1 DE2656747 A1 DE 2656747A1 DE 19762656747 DE19762656747 DE 19762656747 DE 2656747 A DE2656747 A DE 2656747A DE 2656747 A1 DE2656747 A1 DE 2656747A1
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- Germany
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- weight
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- active ingredient
- acid
- methyl
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Die vorliegende Erfindung betrifft neue wertvolle Morpholinderivate und ihre Salze und Molekül- und Additionsverbindungen mit guter fungizider Wirkung, Fungizide, die diese Verbindungen enthalten, und Verfahren zur Bekämpfung von Pilzen mit diesen Verb indungen.The present invention relates to new valuable morpholine derivatives and their salts and molecular and addition compounds with good fungicidal activity, fungicides containing these compounds, and methods of combating fungi with these compounds.
Es ist bekannt, N-Tridecyl-2,6-dimethylmorpholin und seine Salze und seine Molekül- und Additionsverbindungen als Fungizide zu verwenden (DT-PS 11 64 152, DT-PS 11 73 722, DT-OS 24 61 513).It is known N-tridecyl-2,6-dimethylmorpholine and its salts and to use its molecular and addition compounds as fungicides (DT-PS 11 64 152, DT-PS 11 73 722, DT-OS 24 61 513).
Es wurde gefunden, daß Morpholinderivate der FormelIt has been found that morpholine derivatives of the formula
3 ι CH.. , k ™ · /R 3 ι CH .., k ™ · / R
CH3-C-H^ XV CH2-CH-CH2-N 0CH 3 -CH ^ X V CH 2 -CH-CH 2 -N 0
CH, j iv j.CH, j iv j.
^ R^ RH ^ R ^ R H
in der R1, R2, R5 und R Wasserstoff oder Methyl oder Äthyl bedeuten und ihre Salze, Molekül- und Additionsverbindungen eine gute fungizide Wirkung haben, die der Wirkung der bekannten Morpholinderivate überlegen ist.in which R 1 , R 2 , R 5 and R are hydrogen or methyl or ethyl and their salts, molecular and addition compounds have a good fungicidal effect which is superior to the effect of the known morpholine derivatives.
Salze sind beispielsweise die Salze mit anorganischen oder organischen Säuren, z.Bo Chloride, Fluoride, Bromide, Jodide, Sulfate, Nitrate, Phosphate, Acetate, Propionate» Molekül- oder Additionsverbindungen entstehen beispielsweise mit Säuren von Tensiden, z.B. Dodecylbenzolsulfonsäure.Salts include the salts with inorganic or organic acids, for example o chlorides, fluorides, bromides, iodides, sulfates, nitrates, phosphates, acetates, propionates "molecular or addition compounds are formed for example with acids of surfactants, such as dodecylbenzenesulfonic acid.
Die neuen Verbindungen können, soweit es sich um die 2,6-Dimethylderivate handelt, als eis- und trans-Isomere isoliert werden. Ihre Herstellung erfolgt beispielsweise durch Umsetzung von 2,6-The new compounds can, insofar as they are the 2,6-dimethyl derivatives acts, are isolated as cis and trans isomers. They are produced, for example, by converting 2.6-
480/76 809826/0021 480/76 809826/0021
- sr- ο.ζ, 22 325- sr- ο.ζ, 22 325
Dimethylmorpholin mit 3-p-Tertiär-butyl-phenyl-2-methyl-propanal in Gegenwart eines Verdünnungsmittels, z0Bo Ameisensäure bei Temperaturen von 50 bis 110 C.Dimethylmorpholine with 3-p-tert-butyl-phenyl-2-methyl-propanal in the presence of a diluent, e.g. 0 B o formic acid at temperatures from 50 to 110 C.
Die folgenden Beispiele erläutern die Herstellung der neuen Verbindungen» The following examples explain the preparation of the new compounds »
Synthese von N(3-p-tert.-Butyl-phenyl-2-methyl-l-propyl)-cis-2,6-dimethylmorpholin Synthesis of N (3-p-tert-butyl-phenyl-2-methyl-1-propyl) -cis-2,6-dimethylmorpholine
2,6-Dimethylmorpholin, das durch mit Schwefelsäure katalysierter
Cyclisierung von Di-isopropanolamin gewonnen wurde, wird durch fraktionierte Destillation über eine mit Edelstahldrahtnetzwendeln
gefüllte Destillationskolonne in die eis- und trans-Porm aufgetrennt.
Ca» 75 % (Gew.%) des 2,6-Dimethylmorpholins liegen in der
cis-Form vor, der Rest in trans-Fornu Die Trennung der Isomeren
durch fraktionierte Destillation gelingt an einer Kolonne mit etwa 40 Trennstufen. Die cis-Form geht als 99#iges Produkt bei 80 8l°C
unter einem Druck von 100 Torr über. Die trans-Form des 2,6-Dimethylmorpholins kann unter den gleichen Bedingungen im Übergangs
temperaturbereic
dukt erhalten werden.2,6-Dimethylmorpholine, which was obtained by the cyclization of diisopropanolamine catalyzed with sulfuric acid, is separated into the cis and trans porms by fractional distillation over a distillation column filled with stainless steel wire mesh coils. About 75 % (wt.%) Of the 2,6-dimethylmorpholine are in the cis form, the remainder in the trans form. The isomers are separated by fractional distillation on a column with about 40 separation stages. The cis form goes over as a 99 # product at 80 81 ° C. under a pressure of 100 torr. The trans form of 2,6-dimethylmorpholine can under the same conditions in the transition temperature range
are preserved.
gangstemperaturbereich bei 88 - 89°/100 Torr als über 95%iges Proin einer Rührapparatur, die mit Rückflußkühler, Thermometer und Tropftrichter ausgestattet ist, werden 575 g 98#ige Ameisensäure vorgelegt. Unter Rührung und Kühlung werden danach 3^5 g 99#iges 2,6-cis-Dimethylmorpholin zugetropft. Anschließend wird das Gemisch langsam im Wasserbad auf 70°C erwärmt. Im Verlauf von 4 Stunden werden bei Einhalten einer Temperatur von etwa 100 C zu dem Reaktionsgemisch 612 g 3-p-tert-Butyl-phenyl-2-methyl-propanal zugetropft. Unter starker COp-Entwicklung vollzieht sich die Kondensation. Nach Ablauf der Reaktion wird die Mischung noch zwei Stunden unter Rühren bei 1000C gehalten.transition temperature range at 88-89 ° / 100 torr as more than 95% strength in a stirred apparatus equipped with reflux condenser, thermometer and dropping funnel, 575 g of 98% formic acid are placed. 3 ^ 5 g of 99% 2,6-cis-dimethylmorpholine are then added dropwise with stirring and cooling. The mixture is then slowly heated to 70 ° C. in a water bath. Over the course of 4 hours, while maintaining a temperature of about 100 ° C., 612 g of 3-p-tert-butyl-phenyl-2-methyl-propanal are added dropwise to the reaction mixture. The condensation takes place with a strong COp development. After the reaction has ended, the mixture is kept at 100 ° C. for a further two hours with stirring.
80982Θ/0051 - 3 -80982Θ / 0051 - 3 -
- r- - r- O. Z. 32 325O. Z. 32 325
Danach wird unter vermindertem Druck die überschüssige Ameisensäure abdestilliert. Eine weitgehende Abtrennung der Ameisensäure erfolgt im Vakuum einer Wasserstrahlpumpe bei 1000C.The excess formic acid is then distilled off under reduced pressure. The formic acid is largely separated off in the vacuum of a water jet pump at 100 ° C.
Die Freisetzung der Base aus dem Formiat erfolgt durch Zutropfen von 500 g 40/Siger wäßriger Natronlauge. Das Zugeben der Natronlauge erfolgt zweckmäßig bei 80 - 100°C, um das Vermischen der sich ausbildenden Aminphase mit der Laugenphase zu begünstigen. Um die Viskosität zu erniedrigen, werden 200 g Toluol zugegeben. Die organische Phase wird nach Abtrennen der Laugenphase zweimal mit je 250 g Wasser gewaschen.The base is released from the formate by adding dropwise 500 g of 40% aqueous sodium hydroxide solution. Adding the caustic soda is expediently carried out at 80-100 ° C. in order to promote mixing of the amine phase which is formed with the lye phase. To the To lower the viscosity, 200 g of toluene are added. The organic phase is after separation of the lye phase twice with each Washed 250 g of water.
Zur weiteren Reinigung wird das Amin bei 0,2 Torr über eine Destillationskolonne mit 5 Böden fraktioniert destilliert. Neben einem kleinen Vorlauf (bis 143°C/O,2 Torr; 50 g) werden 865 g N(3-tert.-Butylphenyl-2-methyl-l-propyl)-2,6-cis-dimethylmorpholin erhalten. Diese gehen bei 0,2 Torr zwischen 143 und 146° über. Laut gaschromatographischer Analyse besitzt das Amin einen Gehalt von mehr als 98 % Reinsubstanz» Bezogen auf den Aldehyd wurde eine Ausbeute von 84,5 % erhalten«For further purification, the amine is fractionally distilled at 0.2 torr over a distillation column with 5 trays. In addition to a small forerun (up to 143 ° C./0.2 Torr; 50 g), 865 g of N (3-tert-butylphenyl-2-methyl-1-propyl) -2,6-cis-dimethylmorpholine are obtained. These go over at 0.2 Torr between 143 and 146 °. According to gas chromatographic analysis, the amine has a content of more than 98 % pure substance »Based on the aldehyde, a yield of 84.5 % was obtained«
Zur Überführung in das Hydrochlorid werden 30 g des Reinproduktes in 50 g Äthanol, das bei Raumtemperatur mit Chlorwasserstoff gesättigt wurde, gelöst. Nach dem Abkühlen werden 23 g des bei 220 schmelzenden Hydrochlorids in sehr reiner Form erhalten.30 g of the pure product are used for conversion into the hydrochloride dissolved in 50 g of ethanol which has been saturated with hydrogen chloride at room temperature. After cooling, 23 g of the at 220 Melting hydrochloride obtained in very pure form.
Synthese von N(3-p-tert.Butylphenyl-2-methyl-l-propyl)-2,6-transdime thylmorpholinSynthesis of N (3-p-tert-butylphenyl-2-methyl-1-propyl) -2,6-transdime thylmorpholine
In 70 g 98#ige Ameisensäure werden 29 g 2,6-trans-Dimethylmorpholin unter Kühlung mit Eis eingetragen. Unter Rührung werden dann 41 g 3-p-tert.Butylphenyl-2-methyl-propanal zugegeben. Das Reaktionsgemisch wird 6 Stunden auf 1000C erhitzt. Zu Beginn der Umsetzung ze ißt sich eine sehr starke CO^Entwicklung, die nach29 g of 2,6-trans-dimethylmorpholine are introduced into 70 g of 98% formic acid while cooling with ice. 41 g of 3-p-tert-butylphenyl-2-methylpropanal are then added with stirring. The reaction mixture is heated to 100 ° C. for 6 hours. At the beginning of the implementation there is a very strong CO ^ development, which is after
809826/0021809826/0021
- 1Jf - 1 Jf
O0Z. 32 325O 0 line 32 325
etwa einer Stunde merklich nachläßt. Die weitere Aufarbeitung erfolgt wie unter Beispiel 1 näher erläutert wurde.noticeably decreases for about an hour. The further work-up takes place as explained in more detail under Example 1.
Bei 5 Torr geht das N(3-p-tert„Butylphenyl-2-methyl-l-propyl)-2,6-trans-dimethylmorpholin bei 168 - I690 über0 Ausbeute 52 g = 86 % bezogen auf Aldehyd. 11 g des Amins werden in 20 g Essigester, der mit trockenem Chlorwasserstoff gesättigt wurde, gelöst. Beim Abkühlen kristallisiert das Hydrochlorid aus, Pp I65 C.At 5 torr is the N (3-p-tert "butylphenyl-2-methyl-l-propyl) -2,6-trans-dimethylmorpholine at 168 - I69 0 0 yield about 52 g = 86% based on aldehyde. 11 g of the amine are dissolved in 20 g of ethyl acetate which has been saturated with dry hydrogen chloride. The hydrochloride crystallizes out on cooling, Pp I65 C.
Die anderen Verbindungen werden in entsprechender Weise erhalten.The other compounds are obtained in a similar manner.
Von den erfindungsgemäßen Verbindungen werden beispielsweise die folgenden genannt:Of the compounds according to the invention, for example called the following:
CH,CH,
CH3-CCH 3 -C
CH3 CH 3
CH, VcH2-CH-CH2 CH, VcH 2 -CH-CH 2
Wirkstoff Nr.Active ingredient no.
R"VJ R "VJ
CH,CH,
Kp: 123°C/O,O1 TorrBp: 123 ° C / O, O1 torr
/—\/ - \
R-N, 0 .HR-N, 0 .H
/CH/ CH
R-N 0R-N 0
NCH3 cis-Porm N CH 3 cis porm
/—CCH7/ —C CH 7
R-N 0R-N 0
CH3 trans-PormCH 3 trans porm
Pp: 1080CPp: 108 0 C
Kp: 143-1^6°Ο/Ο,2 Torr Kp: l68-l69°C/5 TorrBp: 143-1 ^ 6 ° Ο / Ο, 2 Torr Bp: l68-l69 ° C / 5 Torr
809826/0021809826/0021
O.Z.O.Z.
R-N O .HClR-N O .HCl
XH3 cis-FormXH 3 cis form
OH,OH,
» HCl“HCl
R-N ΟR-N Ο
^CH3 trans-Form^ CH 3 trans form
R-NR-N
CH.CH.
CH Fp: 2200CCH m.p .: 220 ° C
Fp: 165 CM.p .: 165 ° C
Kp: 1280C/0,02 TorrBp: 128 ° C / 0.02 Torr
OHOH
R-N ^H Kp: 133 C/0,05 Torr Kp: 125 C/0,02 TorrR-N ^ H bp: 133 C / 0.05 torr Bp: 125 C / 0.02 Torr
R-N H,CR-NH, C
. HCl. HCl
H,C Kp: 17OUC/5,O TorH, C Kp: 17O U C / 5, O gate
Fp: 2O6°CMp: 206 ° C
Kp: 1^5°C/O,3 TorrBp: 1 ^ 5 ° C / 0.3 torr
R-N Ό . HClR-N Ό. HCl
Fp: 172°CMp: 172 ° C
C2H5 Kp: 1480C/0,3 TorrC 2 H 5 bp: 148 ° C / 0.3 torr
809826/0021809826/0021
- tr- ο.ζ. 32 325- tr- ο.ζ. 32 325
18 R-N Ο Kp: 1^6-148°C/O,3 Torr 18 RN Ο Bp: 1 ^ 6-148 ° C / O, 3 Torr
;2H5 ; 2 H 5
IN UIN U
pie erfindungsgemäßen Wirkstoffe und die entsprechenden Fungizide sind insbesondere geeignet zur BekämpTung von Pflanzenkrankheiten, z.B. Erysiphe graminis (echter Mehltau) an Getreide, Erysiphe cichoriacearum (echter Mehltau) an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncinula necator an Reben, Erysiphe polygoni an Bohnen. Sphaerotheca pannosa an Rosen, Microsphaera querci an Eichen, Botrytis cinerea an Erdbeeren, Reben, Mycosphaerella musicola an Bananen, Puccinia-Arten (Rostpilze) an Getreide, Urqmyces appendiculatus und U. phaseoli an Bohnen, Hemileia vastatrix an Kaffee und Rhizoctonia solani. Sie sind systemisch wirksam; sie werden sowohl Über die Wurzeln als auch über die Blätter aufgenommen und im Pflanzengewebe transportiert.pie active ingredients according to the invention and the corresponding fungicides are particularly suitable for combating plant diseases, E.g. Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoriacearum (powdery mildew) on cucurbits, Podosphaera leucotricha on apples, Uncinula necator on vines, Erysiphe polygoni of beans. Sphaerotheca pannosa on roses, Microsphaera querci on oaks, Botrytis cinerea on strawberries, vines, Mycosphaerella musicola on bananas, Puccinia species (rust fungi) on grain, Urqmyces appendiculatus and U. phaseoli on beans, Hemileia vastatrix on coffee and Rhizoctonia solani. They are systemic effective; they are absorbed both via the roots and via the leaves and transported in the plant tissue.
Bei der Anwendung der neuen Wirkstoffe zur Behandlung von Pflanzen gegen Pilzinfektionen liegen die Aufwandmengen zwischen 0,025 und 5 kg Wirkstoff/ha Fläche. Zum Oberflächenschutz von Bäumen oder Früchten können die Wirkstoffe auch in Verbindung mit Kunststoffdispersionen 0,25/Sig bis 5#ig, bezogen auf das Gewicht der Dispersion, verwendet werden» Die Fungizide enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %. When using the new active ingredients for the treatment of plants against fungal infections, the application rates are between 0.025 and 5 kg active ingredient / ha area. To protect the surface of trees or fruits, the active ingredients can also be used in conjunction with plastic dispersions 0.25 / Sig to 5%, based on the weight of the dispersion. The fungicides generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90 %.
Die Wirkstoffe können mit anderen bekannten Fungiziden gemischt werden. In vielen Fällen erhält man dabei eine Vergrößerung des fungiziden Wirkungsspektrums; bei einer Anzahl von Fungizidmischungen in den Gewichtsverhältnis sen 1:10 bis 10:1 treten auch synergistische Effekte- auf, d.h. die fungizide Wirksamkeit des Kombinationsproduktes ist größer als die der addierten Wirksamkeiten der Einzelkomponenten·' Fungizide, die mit den er f indungs gemäßen Verbindungen kombiniert werden können, sind beispielsweise:The active ingredients can be mixed with other known fungicides will. In many cases this results in an enlargement of the fungicidal spectrum of activity; with a number of fungicide mixtures in the weight ratios of 1:10 to 10: 1, synergistic effects also occur Effects - i.e. the fungicidal effectiveness of the combination product is greater than that of the added efficacy of the individual components · 'fungicides with the inventions according to Connections that can be combined are, for example:
Dibhlocarbanate und deren Derivate, wie Zinkdimethyldithiocarbamat, 2 6' " ° 2 1Dibhlocarbanates and their derivatives, such as zinc dimethyldithiocarbamate, 2 6 '"° 2 1
- ir- O0Z. 32 325- ir- O 0 line 32 325
Die Anwendung erfolgt ζ.Β» in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen oder Dispersionen, Emulsionen, öldispersionen, Pasten, Stäubend.tteln, 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 erfindungsgemäßen Wirkstoffe gewährleisten.The application takes place ζ.Β »in the form of directly sprayable solutions, Powders, suspensions or dispersions, emulsions, oil dispersions, Pastes, dusting agents, spreading agents, granulates Spraying, misting, dusting, scattering or watering. The forms of application depend entirely on the intended use; in any case, they should ensure the finest possible distribution of the active ingredients according to the invention.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten und öldispersionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle usw., sowie öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, zum Beispiel Benzol, Toluol, Xylol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate zum Beispiel Methanol, Äthanol, Propanol, Butanol, Chloroform, Tetrachlorkohlenstoff, Cyclohexanol, Cyclohexanon, Chlorbenzol, Isophoron usw«, stark polare Lösungsmittel, ζ,Ββ Dimethylformamid, Dimethylsulfoxid, N-Methylpyrolidon, Wasser usw„ in Betracht.For the production of directly sprayable solutions, emulsions, pastes and oil dispersions, mineral oil fractions with a medium to high boiling point, 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 benzene, toluene, are used Xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, for example methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc. «, strongly polar solvents, ζ, Β β dimethylformamide, dimethyl sulfoxide, N-methyl pyrolidone , Water, etc. “into consideration.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulvern), öldispersionen durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substanzen als solche oder in einem öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous application forms can be obtained from emulsion concentrates, pastes or wettable powders (wettable powders), oil dispersions by addition be prepared by water. For the production of emulsions, pastes or oil dispersions, the substances can be used as such or dissolved in an oil or solvent, using wetting, adhesive, dispersing or emulsifiers are homogenized in water. But it can also consist of active substances, wetting, adhesive, dispersing or concentrates consisting of emulsifiers and possibly solvents or oil are produced which are suitable for dilution with water are.
An oberflächenaktiven Stoffen sind zu nennen: Alkali-, Erdalkali-, Ammoniumsalze von Ligninsulfonsäure, Naphthalinsulfonsäuren, Phenolsulfonsäuren, Alkylary!sulfonate, Alkylsulfate, Alkylsulfonate, Alkali- und Erdalkalisalze der Dibutylnaphthalinsulfonsäure, Lauryläthersulfat, Fettalkoholsulfate, fettsaure Alkali- und Erdalkalisalze, Salze sulfatierter Hexa-The following surface-active substances should be mentioned: alkali, alkaline earth, ammonium salts of lignosulphonic acid, naphthalenesulphonic acids, Phenol sulfonic acids, alkylary sulfonates, alkyl sulfates, Alkyl sulfonates, alkali and alkaline earth salts of dibutylnaphthalene sulfonic acid, Lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth salts, salts of sulfated hexa-
809826/0021 " 9 -809826/0021 "9 -
-if- O.Z. 32-if- O.Z. 32
ο c c cn/πο c c cn / π
Manganäthylenbisdithiocarbamat, Mangan-Zink-äthylendiamin-bis-dithiocarbamat, Zinkäthylenbisdithiocarbamat, Tetramethylthiuramdisulfid,Manganäthylenbisdithiocarbamat, Manganese-zinc-ethylenediamine-bis-dithiocarbamat, Zinc ethylene bisdithiocarbamate, tetramethylthiuram disulfide,
Ammoniak-Komplex von Zink-CNjN-äthylen-bis-dithiocarbamat)Ammonia complex of zinc-CNjN-ethylene-bis-dithiocarbamate)
NjN'-Polyäthylen-bis-CthiocarbamoyD-disulfid, Zink-(N, N ·-propylen-bis-dithioearbamat), Ammoniak-Komplex von Zink-(N,N1-propylen-bis-dithiocarbamat)NjN'-polyethylene-bis-CthiocarbamoyD-disulfide, zinc- (N, N-propylene-bis-dithioearbamate), ammonia complex of zinc- (N, N 1 -propylene-bis-dithiocarbamate)
N,N'-Polypropylen-bis-(thiocarbamoyl)-disulfid; heterocyclische Verbindungen, wie N-Trichlormethylthio-tetrahydrophthalimid, N-Trichlormethylthio-phthalimid, N-(1,1,2,2-Tetrachloräthylthio)-tetrahydrophthalimid, l-(Butylcarbamoyl)-2-benzimidazol-carbaminsäuremethy!ester, 2-Methyloxycarbonylamino-benzimidazol, 2,3-Dihydro-5-carboxanilido-6-methyl-l,4-oxathiin-4,4-dioxid, 2,3-Dihydro-5-carboxanilido-6-methyl-l,4-oxathiin, 5-Butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidin, l,2-Bis-(3-äthoxycarbonyl-2-thioureido)-benzol, l,2-Bis-(3-methoxycarbonyl-2-thioureido)-benzol und verschiedene andere Fungizide, wie Dodecylguanidinacetat,N, N'-polypropylene bis (thiocarbamoyl) disulfide; heterocyclic compounds, such as N-trichloromethylthio-tetrahydrophthalimide, N-trichloromethylthio-phthalimide, N- (1,1,2,2-tetrachloroethylthio) -tetrahydrophthalimide, l- (Butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methyloxycarbonylamino-benzimidazole, 2,3-Dihydro-5-carboxanilido-6-methyl-1,4-oxathiine-4,4-dioxide, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine, 1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-methoxycarbonyl-2-thioureido) benzene and various other fungicides, such as dodecylguanidine acetate,
N-Dichlorfluormethylthio-N',N'-dimethyl-N-pheny1-schwefelsäurediamid, N-dichlorofluoromethylthio-N ', N'-dimethyl-N-pheny1-sulfuric acid diamide,
2,5-Dimethyl-furan-3-carbonsäureanilid, 2,5-Dimethyl-furan-3-carbonsäure-cyclohexylamid, 2-Jodbenzoesäureanilid,2,5-dimethyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide, 2-iodobenzoic acid anilide,
2-Brombenzoesäureanilid,2-bromobenzoic acid anilide,
3-Nitro-isophthalsäure-diisopropylester,3-nitro-isophthalic acid diisopropyl ester,
1-(1,2,4-Triazolyl-l·)-ll-(4f-chlorphenoxy )Ί -3,3-dimethylbutan-1- (1,2,4-Triazolyl-l) -ll- (4 f -chlorphenoxy) Ί -3,3-dimethylbutane
l-(l-Imidazolyl)-2-allyloxy-2-(2,4-dichlorphenyl)-äthan, Piperazin-l,4-diyl-bis-l-(2,2,2-Trichloräthyl)-formamid, 2»^»5»6-Tetrachlor*isophthalonitril, l,2-Dimethyl-3,5-diphenyl-pyrazoliniummethylsulfat.l- (l-imidazolyl) -2-allyloxy-2- (2,4-dichlorophenyl) ethane, Piperazine-1,4-diyl-bis-1- (2,2,2-trichloroethyl) formamide, 2 »^» 5 »6-tetrachlor * isophthalonitrile, 1,2-dimethyl-3,5-diphenyl-pyrazolinium methyl sulfate.
809826/0021 . - 8 -809826/0021. - 8 -
O.Z. 32O.Z. 32
Wirkstoff Nr.Active ingredient no.
(bekannt)(known)
CH.CH.
CH.CH.
0 .CH5COOH0 .CH 5 COOH
CH-CH-
(bekannt)(known)
(bekannt)(known)
Blätter von in Töpfen gewachsenen Weizenkeimlingen der Sorte "Jubilar" werden mit wäßrigen Emulsionen aus 80 % (Gewichtsprozent) Wirkstoff und 20 % Emulgiermittel besprüht und nach dem Antrocknen des Spritzbelages mit Oidien (Sporen) des Weizenmehltaus (Erysiphe graminis var. tritici) bestäubt. Die Versuchspflanzen werden anschließend im Gewächshaus bei Temperaturen zwischen und 22°C und 75 bis 80 % relativer Luftfeuchtigkeit aufgestellt. Nach 10 Tagen wird das Ausmaß der Mehltaupilzentwicklung ermittelt.Leaves of potted wheat seedlings of the "Jubilar" variety are sprayed with aqueous emulsions of 80% (percent by weight) active ingredient and 20 % emulsifier and, after the spray coating has dried on, dusted with oidia (spores) of wheat powdery mildew (Erysiphe graminis var. Tritici). The test plants are then placed in a greenhouse at temperatures between and 22 ° C. and 75 to 80 % relative humidity. The extent of powdery mildew development is determined after 10 days.
WirkstoffActive ingredient
Befall der Blätter nach Spritzungen mit χ #iger WirkstoffbrüheInfestation of the leaves after spraying with χ #iger active ingredient broth
0,0250.025
0,050.05
1 2 3 41 2 3 4
5 65 6
809826/0021809826/0021
- 11 -- 11 -
- ^- ■ O.Z. 32 325- ^ - ■ O.Z. 32 325
decanole, Heptadecanole, Octadecanole, Salze von sulfatiertem Fettalkoholglykolather, Kondensationsprodukte von sulfonierten! Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw» der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyäthylen-octylphenoläther, äthoxyliertes Isooctylphenol-, Octy!phenol-, Nonylphenol, Alkylphenolpolyglykoläther. Tributylphenylpolyglykoläther, Alkylarylpolyätheralkohole, Isotridecy!alkohol, Fettalkoholäthylenoxid-Kondensate, äthoxyliertes Rizinusöl, Polyoxyäthylenalkyläther, äthoxyliertes Polyoxypropylen, Laurylalkoholpolyglykolätheracetal, Sorbitester, Lignin, Sulfitablaugen und Methylcellulose.decanols, heptadecanols, octadecanols, salts of sulfated Fatty alcohol glycol ethers, condensation products of sulfonated! Naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether. Tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecy alcohol, fatty alcohol ethylene oxide condensates, ethoxylated Castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, Lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulphite waste liquors and methyl cellulose.
Pulver, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden»Powder, grit and dust can be mixed or mixed together Milling the active substances with a solid carrier material »
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind z.Bo Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Talkum, Bolus, Löß, Ton, Dolomit, Diatemeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z»Bo Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehle, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe«Granules, for example coated, impregnated and homogeneous granules, can be produced by binding the active ingredients to solid carriers. Solid carriers are, for example , mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, talc, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as "B o ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as grain flours, tree bark, wood and nut shell flour, cellulose powder and other solid carriers"
Zu den Mischungen oder Einzelwirkstoffen können öle verschiedenen Typs, Herbizide, Fungizide, Nematozide, Insektizide, Bakterizide, Spurenelemente, Düngemittel, Antischaummittel (z.B„ Silikone), Wachstumsregulatoren, Antidotmittel oder andere wirksame Verbindungen, zugesetzt werden.In addition to the mixtures or individual active ingredients, oils can be different Type, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoam agents (e.g. "silicones), Growth regulators, antidotes, or other effective compounds, can be added.
Für die folgenden Versuche wurden folgende bekannte Vergleichssubstanzen verwendet» The following known reference substances were used for the following experiments »
— 1 ο — 809826/0021- 1 ο - 809826/0021
- ο.ζ. 32 325- ο.ζ. 32 325
80 % des zu prüfenden Wirkstoffes und 20 % Natriumligninsulfonat enthalten, besprüht und im Gewächshaus bei Temperaturen zwischen 20 und 22°C und bei 75 - 80 % relativer Luftfeuchtigkeit aufgestellt. Nach 10 Tagen wird das Ausmaß der Rostpilzentwicklung beurteilt. Containing 80 % of the active ingredient to be tested and 20 % sodium ligninsulphonate, sprayed and placed in a greenhouse at temperatures between 20 and 22 ° C and at 75-80 % relative humidity. The extent of the rust fungus development is assessed after 10 days.
0 = kein Befall, abgestuft bis 5 = Totalbefall Beispiel 60 = no infestation, graduated to 5 = total infestation Example 6
Man vermischt 90 Gewichtsteile der Verbindung 3 mit 10 Gewichtsteilen N-Methyl-iX-pyrrolidon und erhält eine Lösung, die zur Anwendung in Form kleinster Tropen geeignet ist.90 parts by weight of compound 3 are mixed with 10 parts by weight of N-methyl-iX-pyrrolidone and a solution is obtained which is suitable for use is suitable in the form of the smallest tropics.
20 Gewichtsteile der Verbindung 4 werden in einer Mischung gelöst, die aus 80 Gewichtsteilen Xylol, 10 Gewichtsteilen 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 Xthylenoxid an 1 Mol Ricinusöl besteht. Durch Ausgießen und feines20 parts by weight of compound 4 are dissolved in a mixture from 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 calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring out and fine
809826/0021 - 13 -809826/0021 - 13 -
O = kein Befall, abgestuft bis 5 = Totalbefall Beispiel 4O = no infestation, graded up to 5 = total infestation Example 4
In einem weiteren Versuch werden, wie in Beispiel 3 beschrieben, Blätter von in Töpfen gewachsenen Gerstenkeimlingen der Sorte "Pirlbecks Union" behandelt und mit Sporen (Konidien) des Gerstenmehltaus (Erysiphe graminis var. hordei) bestäubt.In a further experiment, as described in Example 3, leaves of potted barley seedlings of the variety "Pirlbecks Union" treated and with spores (conidia) of barley powdery mildew (Erysiphe graminis var. Hordei) pollinated.
Wirkstoff Befall der Blätter nach SpritzungenActive ingredient Infestation of the leaves after spraying
mit χ £iger Wirkstoffbrühewith £ iger active ingredient broth
χ = 0,006 0,012 0,025χ = 0.006 0.012 0.025
0 = kein Befall, abgestuft bis 5 = Totalbefall Beispiel 50 = no infestation, graduated up to 5 = total infestation example 5
* Blätter von in Topfen gewachsenen Weizenpflanzen werden mit Spo- ■] ren des itfeizenbraunrostes (Puccinia recondita) künstlich infiziert *-; und 48 Stunden lang bei 20 - 25°C in einer wasserdampf gesättigten . ü Kammer aufgestellt» Danach werden die Pflanzen mit wäßrigen Spritzbrühen, die in dem Wasser gelöst oder emulgiert eine Mischung aus* Leaves of wheat plants grown in pots are artificially infected with ■] spores of the brown rust (Puccinia recondita) * -; and for 48 hours at 20 - 25 ° C in a saturated water vapor. ü Chamber set up »After that, the plants are mixed with aqueous spray mixtures, which are dissolved or emulsified in the water
809826/0021809826/0021
- 12 -- 12 -
ο.ζ. 32 325ο.ζ. 32 325
Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält.Distributing the solution in 100,000 parts by weight of water gives an aqueous dispersion containing 0.02 percent by weight of the active ingredient contains.
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 those from 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles Ethylene oxide in 1 mole of isooctylphenol and 10 parts by weight of the adduct consists of 40 moles of ethylene oxide in 1 mole of castor oil. By pouring the solution into 100,000 and finely distributing it Parts by weight of water gives an aqueous dispersion which Contains 0.02 percent 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 28O°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 that 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 Castor oil consists of * by pouring the solution into it and distributing it finely in 100,000 parts by weight of water an aqueous dispersion is obtained which contains 0.02 percent by weight of the active ingredient.
20 Gewichtsteile des Wirkstoffs 5 werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutylnaphthalin-^-sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer SuI-fit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. 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 the active ingredient 5 with 3 parts by weight of the sodium salt of diisobutylnaphthalene - ^ - sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid from a SuI-fit waste liquor and 60 parts by weight of powdered silica gel are mixed well and ground in a hammer mill. By fine Distributing the mixture in 20,000 parts by weight of water gives a spray mixture which contains 0.1 percent by weight of the active ingredient.
809826/0021809826/0021
O.Z. 32 325O.Z. 32 325
3 Gewichtsteile der Verbindung 3 werden mit 97 Gewichtsteilen feinteiligem 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. One gets in this way a dust containing 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 mixed with 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil on the surface of this silica gel was sprayed, intimately mixed. In this way, a preparation of the active ingredient with good adhesion is obtained.
40 Gewichtsteile des Wirkstoffs 3 werden mit 10 Teilen Natriumsalz eines Phenolsulfonsäure^harnstoff-formaldehyd-Kondensats, 2 Teilen Kieselgel und 48 Teilen Wasser innig vermischt. Man erhält eine stabile wäßrige Dispersion* Durch Verdünnen mit 100 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,04 Gewichtsprozent Wirkstoff enthält.40 parts by weight of the active ingredient 3 are mixed with 10 parts of the sodium salt of a phenol sulfonic acid ^ urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water are intimately mixed. A stable aqueous dispersion is obtained * by diluting with 100 Parts by weight of water give an aqueous dispersion which contains 0.04 percent by weight of active ingredient.
20 Teile des Wirkstoffs 4 werden mit 2, Teilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Teile 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 the active ingredient 4 are intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.
809826/0021809826/0021
Claims (4)
Priority Applications (30)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2656747A DE2656747C2 (en) | 1976-12-15 | 1976-12-15 | Morpholine derivatives |
CA291,886A CA1086734A (en) | 1976-12-15 | 1977-11-28 | Morpholine derivatives |
NLAANVRAGE7713685,A NL190012C (en) | 1976-12-15 | 1977-12-09 | PROCESS FOR PREPARING A FUNGICIDE AND PROCESS FOR PREPARING AN N- (3-P-TERT-BUTYLPHENYL-2-METHYL-1-PROPYL) -2,6-DIMETHYL-MORPHOLINE. |
CH1530877A CH635729A5 (en) | 1976-12-15 | 1977-12-12 | Fungicides containing morpholine derivatives as active ingredient |
JP14823877A JPS5377070A (en) | 1976-12-15 | 1977-12-12 | Morpholine derivative and fungicide containing said derivative |
CS778307A CS195346B2 (en) | 1976-12-15 | 1977-12-12 | Fungicide |
BR7708252A BR7708252A (en) | 1976-12-15 | 1977-12-12 | FUNGICIDAL COMPOSITIONS BASED ON MORPHOLINE DERIVATIVES |
HU77BA3607A HU178175B (en) | 1976-12-15 | 1977-12-13 | Fungicide compositions containing morpholine derivatives and process for producing the active agents |
DD77202589A DD134040A5 (en) | 1976-12-15 | 1977-12-13 | FUGICIDE MEDIUM |
PL1977202897A PL106524B1 (en) | 1976-12-15 | 1977-12-13 | FUNGICIDE |
IT52207/77A IT1092170B (en) | 1976-12-15 | 1977-12-14 | MORFOLINA DERIVATIVES |
SU772553299A SU667101A3 (en) | 1976-12-15 | 1977-12-14 | Fungicide |
DK556577A DK145625C (en) | 1976-12-15 | 1977-12-14 | MORPHOLINE DERIVATIVES WITH FUNGICIDE EFFECT FOR USE IN PLANT PROTECTION, FUNGICIDE AGENT AND PROCEDURES TO COMBAT FUNGI |
GB51961/77A GB1591267A (en) | 1976-12-15 | 1977-12-14 | Morpholine derivatives and their use as fungicides |
AT893177A AT356455B (en) | 1976-12-15 | 1977-12-14 | FUNGICIDE |
BE183431A BE861828A (en) | 1976-12-15 | 1977-12-14 | MORPHOLINE DERIVATIVES |
NZ185971A NZ185971A (en) | 1976-12-15 | 1977-12-14 | Morpholine derivatives |
FR7737918A FR2374315A1 (en) | 1976-12-15 | 1977-12-15 | MORPHOLINE DERIVATIVES FOR USE AS FUNGICIDES |
LU79385A LU79385A1 (en) | 1976-12-15 | 1978-04-06 | PROCESS FOR THE PRODUCTION OF MORPHOLINE DERIVATIVES |
YU827/78A YU40701B (en) | 1976-12-15 | 1978-04-06 | Process for obtaining morpholine derivatives |
NO781229A NO146026C (en) | 1976-12-15 | 1978-04-07 | PESTICIDE MORPHOLINE DERIVATIVES |
SE7804074A SE441527B (en) | 1976-12-15 | 1978-04-11 | FUNGICIDICALLY EFFECTIVE MORPHOLINE DERIVATIVES |
FI781117A FI67379C (en) | 1976-12-15 | 1978-04-12 | SAOSOM FUNGISIDER ANVAENDBARA MORFOLINDERIVAT |
AU35565/78A AU3556578A (en) | 1976-12-15 | 1978-04-28 | Morpholine derivatives |
IN499/CAL/78A IN149397B (en) | 1976-12-15 | 1978-05-09 | |
OA56510A OA05971A (en) | 1976-12-15 | 1978-05-25 | Morpholine derivatives. |
GT197956487A GT197956487A (en) | 1976-12-15 | 1979-02-21 | MORPHOLINE DERIVATIVES. |
KE3165A KE3165A (en) | 1976-12-15 | 1981-09-30 | Morpholine derivatives and their use as fungicides |
MY333/85A MY8500333A (en) | 1976-12-15 | 1985-12-30 | Morpholine derivatives and their use as fungicides |
MD95-0017A MD323C2 (en) | 1976-12-15 | 1994-12-13 | Fungicide composition |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2656747A DE2656747C2 (en) | 1976-12-15 | 1976-12-15 | Morpholine derivatives |
NO781229A NO146026C (en) | 1976-12-15 | 1978-04-07 | PESTICIDE MORPHOLINE DERIVATIVES |
FI781117A FI67379C (en) | 1976-12-15 | 1978-04-12 | SAOSOM FUNGISIDER ANVAENDBARA MORFOLINDERIVAT |
AU35565/78A AU3556578A (en) | 1976-12-15 | 1978-04-28 | Morpholine derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2656747A1 true DE2656747A1 (en) | 1978-06-29 |
DE2656747C2 DE2656747C2 (en) | 1984-07-05 |
Family
ID=36763781
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2656747A Expired DE2656747C2 (en) | 1976-12-15 | 1976-12-15 | Morpholine derivatives |
Country Status (28)
Country | Link |
---|---|
JP (1) | JPS5377070A (en) |
AT (1) | AT356455B (en) |
AU (1) | AU3556578A (en) |
BE (1) | BE861828A (en) |
BR (1) | BR7708252A (en) |
CA (1) | CA1086734A (en) |
CH (1) | CH635729A5 (en) |
CS (1) | CS195346B2 (en) |
DD (1) | DD134040A5 (en) |
DE (1) | DE2656747C2 (en) |
DK (1) | DK145625C (en) |
FI (1) | FI67379C (en) |
FR (1) | FR2374315A1 (en) |
GB (1) | GB1591267A (en) |
HU (1) | HU178175B (en) |
IN (1) | IN149397B (en) |
IT (1) | IT1092170B (en) |
KE (1) | KE3165A (en) |
LU (1) | LU79385A1 (en) |
MY (1) | MY8500333A (en) |
NL (1) | NL190012C (en) |
NO (1) | NO146026C (en) |
NZ (1) | NZ185971A (en) |
OA (1) | OA05971A (en) |
PL (1) | PL106524B1 (en) |
SE (1) | SE441527B (en) |
SU (1) | SU667101A3 (en) |
YU (1) | YU40701B (en) |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2822326A1 (en) * | 1978-05-22 | 1979-11-29 | Basf Ag | ANTIMYCOTIC AGENTS |
EP0007093A1 (en) * | 1978-07-14 | 1980-01-23 | BASF Aktiengesellschaft | Process for preparing stereoisomeric N-aralkyl-2,6-dimethylmorpholines |
EP0007479A1 (en) * | 1978-07-08 | 1980-02-06 | BASF Aktiengesellschaft | N-Arylpropyl-substituted cyclic amines, fungicides containing these compounds, and process for the preparation thereof |
EP0014999A1 (en) * | 1979-02-27 | 1980-09-03 | BASF Aktiengesellschaft | Optically active forms of 4-(3-(p-tert.-butylphenyl)-2-methylpropyl)-cis-2,6-dimethylmorpholine and their salts; fungicides containing these compounds and process for their preparation |
EP0017893A1 (en) * | 1979-04-11 | 1980-10-29 | BASF Aktiengesellschaft | Process for the preparation of heterocyclic tertiary aralkyl amines |
FR2463767A1 (en) * | 1979-08-17 | 1981-02-27 | Hoffmann La Roche | NOVEL CIS-4- (3-PHENYL-2-METHYL-PROPYL) -2,6-DIMETHYL-MORPHOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND MEDICAMENTS CONTAINING SAME |
EP0025882A1 (en) * | 1979-09-01 | 1981-04-01 | BASF Aktiengesellschaft | N-Phenylpropyl-substituted azoles, process for their preparation and fungicides containing them |
EP0032659A1 (en) * | 1980-01-16 | 1981-07-29 | BASF Aktiengesellschaft | Optically active derivatives of phenylpropane, their preparation and use in the preparation of fungicides |
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AT354187B (en) | 1976-11-22 | 1979-12-27 | Hoffmann La Roche | FUNGICIDE AGENT |
DE2727482A1 (en) * | 1977-06-18 | 1979-01-11 | Basf Ag | DERIVATIVES OF CYCLIC AMINES |
CH644113A5 (en) * | 1979-08-17 | 1984-07-13 | Hoffmann La Roche | N-substituted 2,6-dimethylmorpholine compounds |
EP0072156B1 (en) * | 1981-07-31 | 1984-11-28 | Fbc Limited | Fungicidal composition containing prochloraz |
EP0074005B1 (en) * | 1981-08-29 | 1985-05-02 | BASF Aktiengesellschaft | Fungicides containing phenylpropylammonium salt, and process for combating fungi |
DE3217964A1 (en) * | 1982-05-13 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING CIS-2-, 6-DIMETHYLMORPHOLIN |
EP0188887B1 (en) * | 1985-01-17 | 1991-05-02 | Imperial Chemical Industries Plc | Tertiary amine compounds |
GB2192881A (en) * | 1986-07-16 | 1988-01-27 | Ici Plc | Tertiary amine compounds |
DE3627071A1 (en) * | 1986-08-09 | 1988-02-11 | Bayer Ag | SUBSTITUTED HYDROXYPROPYLAMINE DERIVATIVES |
FI874121A (en) * | 1986-09-24 | 1988-03-25 | Sumitomo Chemical Co | HETEROCYCLISKA FOERENINGAR, OCH DERAS FRAMSTAELLNING OCH ANVAENDNING. |
DE3633520A1 (en) * | 1986-10-02 | 1988-04-14 | Huels Chemische Werke Ag | METHOD FOR PRODUCING N-SUBSTITUTED MORPHOLIN AND PIPERIDINE DERIVATIVES |
US5135955A (en) * | 1988-04-25 | 1992-08-04 | Eli Lilly And Company | Propanamine derivatives |
DE3902509A1 (en) * | 1989-01-28 | 1990-08-09 | Basf Ag | FUNGICIDAL MIXTURE |
DE3918978A1 (en) * | 1989-06-10 | 1990-12-13 | Wolman Gmbh Dr | MIXING FOR WOOD PROTECTION |
IT1240427B (en) * | 1990-03-02 | 1993-12-15 | Ministero Dall Uni E Della Ric | ARILPROPILAMINE WITH ANTI-Fungal Action |
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EP3429358A1 (en) | 2016-03-16 | 2019-01-23 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits |
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AT354187B (en) * | 1976-11-22 | 1979-12-27 | Hoffmann La Roche | FUNGICIDE AGENT |
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1976
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1977
- 1977-11-28 CA CA291,886A patent/CA1086734A/en not_active Expired
- 1977-12-09 NL NLAANVRAGE7713685,A patent/NL190012C/en not_active IP Right Cessation
- 1977-12-12 CS CS778307A patent/CS195346B2/en unknown
- 1977-12-12 JP JP14823877A patent/JPS5377070A/en active Pending
- 1977-12-12 BR BR7708252A patent/BR7708252A/en unknown
- 1977-12-12 CH CH1530877A patent/CH635729A5/en not_active IP Right Cessation
- 1977-12-13 HU HU77BA3607A patent/HU178175B/en unknown
- 1977-12-13 DD DD77202589A patent/DD134040A5/en unknown
- 1977-12-13 PL PL1977202897A patent/PL106524B1/en unknown
- 1977-12-14 AT AT893177A patent/AT356455B/en not_active IP Right Cessation
- 1977-12-14 NZ NZ185971A patent/NZ185971A/en unknown
- 1977-12-14 SU SU772553299A patent/SU667101A3/en active
- 1977-12-14 GB GB51961/77A patent/GB1591267A/en not_active Expired
- 1977-12-14 IT IT52207/77A patent/IT1092170B/en active
- 1977-12-14 DK DK556577A patent/DK145625C/en not_active IP Right Cessation
- 1977-12-14 BE BE183431A patent/BE861828A/en not_active IP Right Cessation
- 1977-12-15 FR FR7737918A patent/FR2374315A1/en active Granted
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1978
- 1978-04-06 LU LU79385A patent/LU79385A1/en unknown
- 1978-04-06 YU YU827/78A patent/YU40701B/en unknown
- 1978-04-07 NO NO781229A patent/NO146026C/en unknown
- 1978-04-11 SE SE7804074A patent/SE441527B/en not_active IP Right Cessation
- 1978-04-12 FI FI781117A patent/FI67379C/en not_active IP Right Cessation
- 1978-04-28 AU AU35565/78A patent/AU3556578A/en active Pending
- 1978-05-09 IN IN499/CAL/78A patent/IN149397B/en unknown
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