DD140412A1 - FUNGICIDAL AGENT FOR CONTROLLING GENUINE FLOUR MUSHROOMS - Google Patents

Abstract

Fungicidal agent for controlling powdery mildew fungi, consisting of N-alkyldimethylmorpholines, characterized in that a mixture of the positionally isomeric compound types (formulas) R = long-chain alkyl (C ind 12 H ind 25-C ind 18 H ind 37, straight or branched) and their appropriate cis / trans forms is applied.

Description

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b) Field of application of the invention:

The invention is used in agriculture for controlling powdery mildew diseases, mainly in cereal cultivars.

c) Characteristic of the known technical solutions:

It is known that long-chain N-Alky! Morpholine possess fungicidal properties and are used especially for controlling powdery mildew fungi «The long-chain N ~ alkyl radical may be straight or branched and the C atoms in the ring of morpholine may optionally be methyl or other Alkyl radicals substituted with 1-2 carbon atoms eein * According to literature and patent information, the 2 "6 position is preferred in terms of fungicidal properties * Ton dan AlkyIrester * Cj ₀ -G., ^ Is a branched C, ^ - rust evidently occupy a special position. On the other hand, in the case of K (n ~ dodecyl) ~ 2, 6 ~ dimethylmorphine, phytotoxic secondary effects may already occur in fungicidal activity, which would jeopardize the practical usefulness (Angc Chern. 77, 327 ( 1965)) "

d) Object of the invention ε

The aim of the invention is to develop from available and inexpensive raw materials an N-alkylmorpholine preparation, which combines good fungicidal properties and plant compatibility.

e.) Y ^ e sen and features of the invention %

The invention is based on the idea that by changing the isomers of the isomeric (position and ice / isomer) isomers of an N-alkyl-dimethylmorpholine it may be possible to obtain

- 2 - 'CUI 4Ü ~ d.

that the fungicidal properties and the plant tolerance could be influenced in a favorable manner. "In this way, even when using non-optimal but available Fe.ttamingemic mixtures, it would be possible to improve the utility value properties by appropriate choice of method The process produced H-Doaecyldimethylmorpholin actually differs in terms of fungicidal activity and phytotoxicity. Thus, the product prepared from a technical 2,2-Dichlopdiisopropylether- (contains about 20 % 2 «2» dichloro-i-propyX-nisropyl-ether), in contrast to literature references and to a product obtained from propylene oxide preparation well effective and not phytotoxic. This fact is evidently explained by the different isomer distribution. * For the iodo-dodecyl-dimethylmorpholine obtained from the chloroether, an investigation revealed an isomer distribution of cis-tetran-2.5- to trans-2,6 and cis ~ 2 _e 6 ~ = 22; 38i40 _f, while the product obtained from propylenoside contained only the 2o6-position isomer with a cie / trans ratio of 6Oi40. It has surprisingly been found in these investigations that the N-dodecyl-2,5-cis- trans isomer mixture is better than 1 In contrast to literature, information about the conditions of the i-iridecyl derivative shows that it is ineffective. "From the biological findings, it can be deduced that the improved bioactive properties of the mixture of isopropyls over the purely additive If the proportion of the 2. ^ isomer remains at least 15 % , then it will probably be due to a synergism t increase the fungicidal activity and the plant tolerance,

laughing elucidate the relationships set forth, the solution of the task according to the invention is by the application of technical 2 _e 2 -Dichlordipropylether-öemisches ^t ^ the isomeric composition of the H-alkyl-dimethylmorpholine consciously change. " Thus, an advantageous improvement d r Gebrauchsv / ert property s (increase f ungiziden effect and plant tolerance) is reached * Of particular use is equilateral j that 2,2 '~ Dichlordipropylether al a uiierwimcohtea byproduct of Propylenbxid-Kerstellung inexpensive und.in large quantities Available* .

f) embodiments; Example 1:

111 barley plants grown at a height of about 15 cm were sprayed with the agent according to the invention, which had been formulated as an emulsion concentrate with 75 % active ingredient, in aqueous emulsion. "After the spray coating had dried, the plants became conidiae powdery mildew inoculated barley (Erysiphe graminis) and then at temperatures and relative humidity * which are favorable for the development of the disease * incubated _β 10 forecast NaOH, the application was carried out to assess the disease Entwicklunge the following table Kr0xikl1eitsbefa.il and plant compatibility of different Ahwendungskonsentrationen ·. · (based on Wirkatoff) compared to known active ingredients shown!

No.' Active substance · -0.015 % 0.03 %

2o N- (h-dodocyl) -2 _e 6-dimethy3lmorphol5i 1 / = b / + 3 * 1 '+ 2 ·· (15 + 85 parts) o / »0 / -

0 sa no infestation

1 ~ infestation

- ~ completely plant compatible : Λ- - significant leaf damage

Example 2%

In the case of spore germemia, the fungicidal action against Botrytis cinerea and A. pergillus was tested together, with different concentrations of the active ingredient and spore suspensions being incubated together ₆ times after 20 hours of incubation at 24 G. The counting of germinated and uncontrolled spores was carried out. the EDCN _"s were then determined ¹ ^ EDNC the values in the following table graphically wave are shown.

Active substance Botrytiij cinerea Aapergillus niger Kr,. EB ₅₀ BD ₉₅ ED ₅₀ ED ₉₅

I ₀ '0.0045 % 0.0048 % 0.0028 % 0.013 % 2 « 0.01 ..« 0.1 $ 0.01 ,,. 0 _t t # 0.01 «, .. 0.1 $ 0, 1%

3. 0 _f 00? 4 % 0.015% 0.0068 % 0.021

Claims (2)

claims 1, Pungicidal composition for controlling powdery mildew fungi, consisting of K ~ alkyldimethylmorpholine ^, characterized in that a mixture of the positionally isomeric compound types CH ₃ CH - CHo CII - CIL O H-R. , O Si - R gh - on / ^x ch ₂ - gh ' I II R Ei langkettiges alkyl. (Ο _: ΐ2 ^ 25 "" ^ 18 ^ 37 "S ^{era <a} - ^e o & ev branches) and their corresponding cis / Tranß-Pormen angev / and't becomes,"" 2 "in composition according to item 1 _S fact .that such quantitative Zusammensetzimg is applied as a necessary consequence of implementation of a aer obtained in DER propylene oxide Eerstellung 2 _e 2 ^f ~ Dichlordipropylether" mixture with the respective Pettamin mixture gives _$ .wherein the proportion of Xl is at least 15 % _e