DE1214471B - Fungicide for crop protection - Google Patents

Description

Fungicide for crop protection It is known substituted cyclohexylmorpholine to be used as fungicidal agents. However, their effect is not satisfactory.

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.

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.

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.

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.

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.

For example, from N-substituted dialkanolamines one obtains with Thionyl halides morpholine salts.

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.

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.

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.

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.

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)

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.