DE1214471B - Fungicide for crop protection - Google Patents

Fungicide for crop protection

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Publication number
DE1214471B
DE1214471B DEB80145A DEB0080145A DE1214471B DE 1214471 B DE1214471 B DE 1214471B DE B80145 A DEB80145 A DE B80145A DE B0080145 A DEB0080145 A DE B0080145A DE 1214471 B DE1214471 B DE 1214471B
Authority
DE
Germany
Prior art keywords
dimethylmorpholine
cyclohexyl
fungicide
crop protection
isopropylcyclohexyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DEB80145A
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German (de)
Inventor
Dr Karl-Heinz Koenig
Dr Ernst-Heinrich Pommer
Dr Walter Sanne
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BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DEB80145A priority Critical patent/DE1214471B/en
Publication of DE1214471B publication Critical patent/DE1214471B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—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
    • C07D295/033—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 carbocyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Fungizid für den Pflanzenschutz Es ist bekannt, substituierte Cyclohexylmorpholine als fungizide Wirkstoffe zu verwendet. Ihre Wirkung befriedigt jedoch nicht.Fungicide for crop protection It is known substituted cyclohexylmorpholine to be used as fungicidal agents. However, their effect is not satisfactory.

Es wurde gefunden, daß Verbindungen der Formel in der R einen Alkyl- oder alkylsubstituierten Cyclohexylrest mit 1 bis 9 Kohlenstoffatomen bedeutet und n die Bedeutung 1 oder 2 hat, wobei R1 und R2 gleich oder verschieden sind, und ihre Salze eine gute fungizide Wirkung haben.It has been found that compounds of the formula in which R denotes an alkyl or alkyl-substituted cyclohexyl radical having 1 to 9 carbon atoms and n denotes 1 or 2, where R1 and R2 are identical or different, and their salts have a good fungicidal effect.

Als Anion der Salze kommen insbesondere die Anionen anorganischer Säuren, z. B. Salzsäure, Schwefelsäure, Salpetersäure, Bromwasserstoffsäure und Phosphorsäure, in Betracht. Auch die Salze organischer Säuren sind als Wirkstoffe geeignet. The more inorganic anions, in particular, are used as the anions of the salts Acids, e.g. B. hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid and Phosphoric acid. The salts of organic acids are also used as active ingredients suitable.

Die erfindungsgemäßen Wirkstoffe können analog bekannten Methoden hergestellt werden. Bei spiel sweise können sie durch Umsetzung von primären oder sekundären Aminen oder Alkanolaminen mit Alkylenoxyden zu Dialkanolaminen und Ringschluß dieser Verbindungen mit dehydratisierenden Mitteln erhalten werden. Die Dehydratisierung kann beispielsweise mit konzentrierter Schwefelsäure, Salzsäure oder Bromwasserstoffsäure oder dehydrati sierenden Katalysatoren, z. B. Aluminiumoxyd, Aluminiumphosphat, Borphosphat, in flüssiger Phase oder in der Gasphase vorgenommen werden. The active compounds according to the invention can analogously to known methods getting produced. For example, you can implement primary or secondary amines or alkanolamines with alkylene oxides to give dialkanolamines and ring closure of these compounds can be obtained with dehydrating agents. The dehydration can for example with concentrated sulfuric acid, hydrochloric acid or hydrobromic acid or dehydrati-generating catalysts, e.g. B. aluminum oxide, aluminum phosphate, Boron phosphate, in the liquid phase or in the gas phase.

Eine weitere Herstellungsmöglichkeit ist die hydrierende Aminierung von Ketonen mit primären Aminoalkoholen zu N-substituierten sekundären Alkanolaminen, die, wie oben bereits beschrieben, mit Alkylenoxyden umgesetzt werden. Die so erhaltenen Dialkanolamine werden in der bereits beschriebenen Weise mit dehydratisierenden Mitteln zu einem heterocyclischen Ring geschlossen. Another production possibility is hydrogenative amination from ketones with primary amino alcohols to N-substituted secondary alkanolamines, which, as already described above, are reacted with alkylene oxides. The so obtained Dialkanolamines are dehydrated in the manner already described Means closed to a heterocyclic ring.

Ferner kann man gegebenenfalls substituierte 2,2'-Dichloralkyläther mit primären Aminen in Gegenwart von säurebindenden Mitteln zu Verbindungen mit einem heterocyclischen Ring umsetzen. Optionally substituted 2,2'-dichloroalkyl ethers can also be used with primary amines in the presence of acid-binding agents to form compounds with implement a heterocyclic ring.

Beispielsweise erhält man aus N-substituiçrten Dialkanolaminen mit Thionylhalogeniden Morpholinsalze. For example, from N-substituted dialkanolamines one obtains with Thionyl halides morpholine salts.

In der folgenden Tabelle sind einige der.erfindungsgemäß zu verwendenden Wirkstoffe aufgeführt. Wirkstoff Kp. bzw. Fp. N-(2'-Butylcyclohexyl)-2,6-dimethylmorpholin .............................. Kp.0,01 76 bis 79°C N-(4'-tert.-Amylcyclohexyl)-2,6*dimethylmorpholin ....,.. Kp.o.os 100 bis 102°C N-(4'-Isoheptylcyclohexyl)-2,6-dimethylmorpholin ........................... | Kp.0,5 149 bis 150°C N-(4'-Isooctylcyclohexyl)-2,6dimethylmorpholin ; ; Kp.0,2 139 bis 142°C N-(4'-Nonylcyclohexyl)-2,6-dimethylmorpholin ............................. Kp.0,2 148 bis 150°C N-(3'-Methyl-6'-isopropylcyclohexyl)-2,6-dimethylmorpholin ................. Kp.0,2 88 bis 89°C N-(4'-Isononylcyclohexyl)-2,6-dimethylmorpholin ........................... Kp.0,3 151 bis 153°C N-(4'-Isoheptylcyclohexyl)-2,6-dimethylmorpholin-hydrochlorid ............... Öl N-(4'-Isoheptylcyclohexyl)-2,6-dimethylmorpholin-acetat ..................... Öl N-(4'-Isooctylcyclohexyl)-2,6-dimethylmorpholin-hydrochlorid ................ Öl N-(4'-Isooctylcyclohexyl)-2,6dimethylmorpholin-acetat .,, l Fortsetzung Wirkstoff Kp. bzw. Fp. N-[4'-(2"-Isopropylcyclohexyl)-cyclohexyl]-2,6-dimethylmorpholin ............ Kp.0,4 169 bis 172°C N-[4'-(2"-Isopropylcyclohexyl)-cyclohexyl]-2,6-dimethylmorpholin-hydrochlorid Fp. 238 bis 239°C N-[4'-(2"-Isopropylcyclohexyl)-cyclohexyl]-2,6-dimethylmorpholin-acetat ....... Öl Die fungizid und/oder fungistatisch wirksamen erfindungsgemäßen Mittel können in üblicher Weise durch Zusatz fester Streckmittel zu Stäubepulvern oder unter Zusatz von Dispergier-, Netz- und/oder Haftmitteln zu festen oder flüssigen Aufbereitungen für die Herstellung von Spritzbrühen verwendet werden. Es ist weiterhin möglich, die erfindungsgemäßen Mittel als Emulsionen oder Lösungen zu verwenden, die nach dem Aerosolverfahren versprüht werden können. Auch die Beimischung anderer Fungizide und/oder Insektizide ist möglich.The following table lists some of the active ingredients to be used according to the invention. Active ingredient Kp. Or Fp. N- (2'-Butylcyclohexyl) -2,6-dimethylmorpholine .............................. bp 0.01 76 up to 79 ° C N- (4'-tert-amylcyclohexyl) -2,6 * dimethylmorpholine ...., .. boiling point 100 to 102 ° C N- (4'-Isoheptylcyclohexyl) -2,6-dimethylmorpholine ........................... | Bp 0.5 149 to 150 ° C N- (4'-isooctylcyclohexyl) -2,6dimethylmorpholine; ; Bp 0.2 139 to 142 ° C N- (4'-Nonylcyclohexyl) -2,6-dimethylmorpholine ............................. Bp 0.2 148 bis 150 ° C N- (3'-methyl-6'-isopropylcyclohexyl) -2,6-dimethylmorpholine ................. b.p. 0.2 88-89 ° C N- (4'-Isononylcyclohexyl) -2,6-dimethylmorpholine ........................... Bp 0.3 151 to 153 ° C. N- (4'-Isoheptylcyclohexyl) -2,6-dimethylmorpholine hydrochloride ............... oil N- (4'-Isoheptylcyclohexyl) -2,6-dimethylmorpholine acetate ..................... oil N- (4'-Isooctylcyclohexyl) -2,6-dimethylmorpholine hydrochloride ................ oil N- (4'-Isooctylcyclohexyl) -2,6dimethylmorpholine acetate. ,, l continuation Active ingredient Kp. Or Fp. N- [4 '- (2 "-Isopropylcyclohexyl) cyclohexyl] -2,6-dimethylmorpholine ............ b.p. 0.4 169-172 ° C N- [4 '- (2 "-Isopropylcyclohexyl) cyclohexyl] -2,6-dimethylmorpholine hydrochloride, m.p. 238-239 ° C N- [4 '- (2 "-Isopropylcyclohexyl) -cyclohexyl] -2,6-dimethylmorpholine acetate ....... oil The fungicidally and / or fungistatically active agents according to the invention can be used in the customary manner by adding solid extenders to dust powders or with the addition of dispersants, wetting agents and / or adhesives to solid or liquid preparations for the production of spray liquors. It is also possible to use the agents according to the invention as emulsions or solutions which can be sprayed by the aerosol method. It is also possible to add other fungicides and / or insecticides.

Die Wirkung der erfindungsgemäß zu verwendenden Verbindungen erstreckt sich besonders auf echte Mehltaupilze, aber auch auf andere Schadpilze, z. B. Botrytis cinerea.The effect of the compounds to be used according to the invention extends particularly on powdery mildew, but also on other harmful fungi, e.g. B. Botrytis cinerea.

Beispiel 1 Blätter von in Töpfen gewachsenen Gerstenkeimlingen werden mit wässerigen Emulsionen aus 80% Wirkstoff und 20% Emulgiermittel besprüht und nach dem Antrocknen des Spritzbelages mit Oidien (Sporen) des Gerstenmehltaus (Erysiphe graminis var. hordei) bestäubt, Die Versuchspflanzen werden anschließend im Gewächshaus bei Temperaturen zwischen 20 und 22°C und 75 bis 800/0 relativer Luftfeuchtigkeit aufgestellt. Nach 10 Tagen wird das Ausmaß der Mehltaupilz-Entwicklung ermittelt. Example 1 Leaves of potted barley seedlings are obtained sprayed with aqueous emulsions of 80% active ingredient and 20% emulsifier and after the spray coating with oidia (spores) of barley powdery mildew (Erysiphe graminis var. hordei), the test plants are then in the greenhouse at temperatures between 20 and 22 ° C and 75 to 800/0 relative humidity set up. The extent of powdery mildew development is determined after 10 days.

Die Zahlen in der Tabelle haben folgende Bedeutung: 0 = kein Befall, abgestuft bis 5 = Totalbefall. Befall der Blätter nach Spritzungen mit *%iger Wirkstoff Wirkstoffbrühe * = 0,0075 - 0,015 0,03 0,06 N-(2'-Butylcyclohexyl)-2,6-dimethylmorpholin ......... 2 1 0 0 0 N-(4'-tert.-Amylcyclohexyl)-2,6-dimethylmorpholin ..... 1 1 0 0 0+ N-(4'-Isoheptylcyclohexyl)-2,6-dimethylmorpholin 1 1 - 0 0 - 0+ N-(4'-Isooctylcyclohexyl)-2,6-dimethylmorpholin ....... | 1 | 0 | 0 | 0 | 0+ N-(4'-Nonylcyclohexyl)-2,6-dimethylmorpholin ; - 2 1 ° ° °+ N-(3'-Methyl-6'-isopropylcyclohexyl)-2,6-dimethyl- morpholin ...................................... 2 2 0 0 0 Vergleichsmittel: N-Cyclohexyl-2,6-dimethylmorpholin ............... 3 3 3 2 2 N-Cyclohexyl-2,6-dimethylmorpholin-acetat ......... 4 3 2 2 2 += Leichte Blattschäden. The numbers in the table have the following meaning: 0 = no infestation, graduated to 5 = total infestation. Infestation of the leaves after spraying with *% Active ingredient broth * = 0.0075 - 0.015 0.03 0.06 N- (2'-Butylcyclohexyl) -2,6-dimethylmorpholine ......... 2 1 0 0 0 N- (4'-tert-amylcyclohexyl) -2,6-dimethylmorpholine ..... 1 1 0 0 0+ N- (4'-Isoheptylcyclohexyl) -2,6-dimethylmorpholine 1 1 - 0 0 - 0+ N- (4'-Isooctylcyclohexyl) -2,6-dimethylmorpholine ....... | 1 | 0 | 0 | 0 | 0+ N- (4'-nonylcyclohexyl) -2,6-dimethylmorpholine; - 2 1 ° ° ° + N- (3'-methyl-6'-isopropylcyclohexyl) -2,6-dimethyl- morpholine ...................................... 2 2 0 0 0 Comparison means: N-Cyclohexyl-2,6-dimethylmorpholine ............... 3 3 3 2 2 N-Cyclohexyl-2,6-dimethylmorpholine-acetate ......... 4 3 2 2 2 + = Slight leaf damage.

B e i s p i e l 2 Blätter von in Töpfen gewachsenen Gurkenkeimlingen werden mit wässerigen Emulsionen aus 80°/o Wirkstoff und 20% Emulgiermittel besprüht und nach dem Antrocknen des Spritzbelages mit Oidien (Sporen) des Gurkenmehltaus (Erysiphe cichoriacearum) bestäubt. Die Versuchspflanzen werden anschließend - im Gewächshaus bei Temperaturen zwischen 20 und 22°C und 75 bis 800/0 relativer Luftfeuchtigkeit aufgestellt. Nach 10 Tagen wird das Ausmaß der Mehltaupilz-Entwicklung ermittelt. Befall der Blätter nach Spritzungen mit *%iger Wirkstoff Wirkstoffbrühe * = 0,0075 0,015 0,03 0,05 0,1 N-(4'-Isohepylcyclohexyl)-2,6-dimethylmorpholin ...... 3 1 0 0 0 N-(4'-Isooctylcyclohexyl)-2,6-dimethylmorpholin ...... 3 2 0 0 0 N-(4'-Isononylcyclohexyl)-2,6-dimethylmorpholin ...... 2 2 0 0 0 N-(4'-Isoheptylcyclohexyl)-2,6-dimethylmorpholin- hydrochlorid .................................... 3 3 1 0 0 N-(4'-Isoheptylcyclohexyl)-2,6-dimethylmorpholin-acetat 2 1 0 0 0 N-(4'-Isooctylcyclohexyl)-2,6-dimethylmorpholin- hydrochlorid .................................... 2 1 0 0 0 N-(4'-Isooctylcyclohexyl)-2,6-dimethylmorpholin-acetat 2 1 0 0 0 Fortsetzung Befall der Blätter nach Spritzungen mit *%iger Wirkstoffbrühe *= 0,0075 0,015 0,03 0,05 0,1 N-[4'-(2"-Isopropylcyclohexyl)-cyclohexyl]- 2,6-dimethylmorpholin ........................... 2 1 0 0 0 N-[4'-(2"-Isopropylcyclohexyl)-cyclohexyl]- 2,6-dimethylmorpholin-hydrochlorid ............... 1 1 0 0 0 N-[4'-(2"-Isopropylcyclohexyl)-cyclohexyl]- 2,6-dimethylmorpholin-acetat ..................... 3 2 1 0 0 Vergleichsmittel: N-Cyclohexyl-2,6-dimethylmorpholin ............... 4 4 2 2 1 N-Cyclohexyl-2,6-dimethylmorpholin-acetat ......... 4 3 2 1 1 Example 2 Leaves of cucumber seedlings grown in pots are sprayed with aqueous emulsions of 80% active ingredient and 20% emulsifier and, after the spray coating has dried on, dusted with oidia (spores) of cucumber powdery mildew (Erysiphe cichoriacearum). The test plants are then - placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 800/0 relative humidity. The extent of powdery mildew development is determined after 10 days. Infestation of the leaves after spraying with *% Active ingredient broth * = 0.0075 0.015 0.03 0.05 0.1 N- (4'-Isohepylcyclohexyl) -2,6-dimethylmorpholine ...... 3 1 0 0 0 N- (4'-Isooctylcyclohexyl) -2,6-dimethylmorpholine ...... 3 2 0 0 0 N- (4'-Isononylcyclohexyl) -2,6-dimethylmorpholine ...... 2 2 0 0 0 N- (4'-Isoheptylcyclohexyl) -2,6-dimethylmorpholine- hydrochloride .................................... 3 3 1 0 0 N- (4'-Isoheptylcyclohexyl) -2,6-dimethylmorpholine acetate 2 1 0 0 0 N- (4'-Isooctylcyclohexyl) -2,6-dimethylmorpholine- hydrochloride .................................... 2 1 0 0 0 N- (4'-Isooctylcyclohexyl) -2,6-dimethylmorpholine acetate 2 1 0 0 0 continuation Infestation of the leaves after spraying with *% Active ingredient broth * = 0.0075 0.015 0.03 0.05 0.1 N- [4 '- (2 "-Isopropylcyclohexyl) -cyclohexyl] - 2,6-dimethylmorpholine ........................... 2 1 0 0 0 N- [4 '- (2 "-Isopropylcyclohexyl) -cyclohexyl] - 2,6-dimethylmorpholine hydrochloride ............... 1 1 0 0 0 N- [4 '- (2 "-Isopropylcyclohexyl) -cyclohexyl] - 2,6-dimethylmorpholine acetate ..................... 3 2 1 0 0 Comparison means: N-Cyclohexyl-2,6-dimethylmorpholine ............... 4 4 2 2 1 N-Cyclohexyl-2,6-dimethylmorpholine-acetate ......... 4 3 2 1 1

Claims (1)

Patentanspruch: Fungizid für den Pflanzenschutz, enthaltend eine Verbindung der Formel in der R einen Alkyl- oder alkylsubstituierten Cyclohexylrest mit 1 bis 9 Kohlenstoffatomen bedeutet und n die Bedeutung 1 oder 2 hat, wobei R1 und R2 gleich oder verschieden sind, oder ein Salz dieser Verbindung.Claim: Fungicide for crop protection, containing a compound of the formula in which R is an alkyl or alkyl-substituted cyclohexyl radical having 1 to 9 carbon atoms and n is 1 or 2, where R1 and R2 are identical or different, or a salt of this compound.
DEB80145A 1965-01-16 1965-01-16 Fungicide for crop protection Pending DE1214471B (en)

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DEB80145A DE1214471B (en) 1965-01-16 1965-01-16 Fungicide for crop protection

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0019764A1 (en) * 1979-05-25 1980-12-10 BASF Aktiengesellschaft Trans-3-(4'-tert.-butyl-cyclohexyl-1')-2-methyl-1-(3'-methylpiperidino, 3',5'-dimethylpiperidino and 2', 6'-dimethylmorpholino) propane, process for their pure preparation, antimycotic agents containing them and their utilisation
EP0129211A1 (en) * 1983-06-16 1984-12-27 BASF Aktiengesellschaft 2,6-Trans-dimethyl morpholine derivatives, fungicides containing them and methods of combating fungi
EP0253501A2 (en) * 1986-07-16 1988-01-20 Imperial Chemical Industries Plc N-disubstituted cycloalkylmethyl amines useful as fungicides
EP0259977A2 (en) * 1986-09-10 1988-03-16 Imperial Chemical Industries Plc Tertiary amine compounds
EP0271750A1 (en) * 1986-12-17 1988-06-22 BASF Aktiengesellschaft Fungicidal cyclohexyl amines
US4897425A (en) * 1986-11-25 1990-01-30 Basf Aktiengesellschaft Fungicidal cyclohexylamines
EP0355540A2 (en) * 1988-08-19 1990-02-28 Bayer Ag Substituted cyclohexyl amines, process for their preparation and their use as pesticides

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0019764A1 (en) * 1979-05-25 1980-12-10 BASF Aktiengesellschaft Trans-3-(4'-tert.-butyl-cyclohexyl-1')-2-methyl-1-(3'-methylpiperidino, 3',5'-dimethylpiperidino and 2', 6'-dimethylmorpholino) propane, process for their pure preparation, antimycotic agents containing them and their utilisation
EP0129211A1 (en) * 1983-06-16 1984-12-27 BASF Aktiengesellschaft 2,6-Trans-dimethyl morpholine derivatives, fungicides containing them and methods of combating fungi
EP0253501A2 (en) * 1986-07-16 1988-01-20 Imperial Chemical Industries Plc N-disubstituted cycloalkylmethyl amines useful as fungicides
EP0253501A3 (en) * 1986-07-16 1990-04-04 Imperial Chemical Industries Plc N-disubstituted cycloalkylmethyl amines useful as fungicides
EP0259977A2 (en) * 1986-09-10 1988-03-16 Imperial Chemical Industries Plc Tertiary amine compounds
EP0259977A3 (en) * 1986-09-10 1990-03-07 Imperial Chemical Industries Plc Tertiary amine compounds
US4897425A (en) * 1986-11-25 1990-01-30 Basf Aktiengesellschaft Fungicidal cyclohexylamines
EP0271750A1 (en) * 1986-12-17 1988-06-22 BASF Aktiengesellschaft Fungicidal cyclohexyl amines
US5071851A (en) * 1986-12-17 1991-12-10 Basf Aktiengesellschaft Fungicidal cyclohexylamines
EP0355540A2 (en) * 1988-08-19 1990-02-28 Bayer Ag Substituted cyclohexyl amines, process for their preparation and their use as pesticides
EP0355540A3 (en) * 1988-08-19 1990-04-25 Bayer Ag Substituted cyclohexyl amines, process for their preparation and their use as pesticides

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