DD229297A1 - FUNGICIDE COMBINATIONS - Google Patents

Abstract

The invention relates to synergistic combinations of known active ingredients and their use in crop protection. The underlying task is to find suitable combination partners for fungicidal N-Alkylmorpholine, which lead to an increase in activity and at the same time counteract resistance training. It is achieved according to the invention in that combinations with metalaxyl have a synergistic increase in activity over a number of harmful fungi and allow a greater range of application. The new agents are particularly suitable for the simultaneous fight against real and false powdery mildew fungi.

Description

- i-

Δ01ΙΓ 43/84 A01H 37/22

Title of the invention Pungicide combinations

Field of application of the invention

The invention relates to synergistic combinations of known fungicidal active compounds and their use in crop protection.

Characteristic of the known technical solutions

H-Alkylmorpholine have as practical fungicidal input. Plant protection found (DO 11 64 152, Di 11 98 125, DD 140 412) "However, a significant shortcoming of such funds consists in the limited field of action against powdery mildew fungi." ... Various acylalanines (DD 118 979 »DD 118 510) have a very good activity against Oomycetenj other economically important fungal pathogens are by these agents, (but not bekbar bar«

For the simultaneous control of real and false downy mildew fungi, it has therefore already been proposed to use H-alkylmorpholines in mixtures with dithiocarbamates (DD 111 014). These combinations yield partly good results but can not be satisfied, above all owing to the exclusively protective mode of action of the dithiocarbamates.

iaailL.1932 * O23O7 5

Object of the invention

The aim of the invention is the development of new combinations with improved efficacy and broader spectrum of use for the destruction of fungal pests »

Explanation of the essence of the invention

The invention has for its object to find suitable combination partners for fungicidal U-alkylmorpholines, which lead to an increase in activity and at the same time counteract resistance training · ...... Surprisingly, it has now been found that in a mixture consisting of

(A) l! -Alkyl-2,6-dimethylmorpholinen the general Pormel I or a combination with their position isomers. U-Alky1-2,5-dimethylmorpholinen of the general formula II

^H 3 ^C ν H ₃ C

^H 3 ^CAN 4h ₃

(I) '(ID

in which R is long-chain alkyl (C ₁₀ -C ₁₈ , straight, branched or cyclic),

and

(B) D, L-N- (2,6-dimethylphenyl) -B '- (2'-methoxyacetyl) alanine methyl ester (III)

CH-CH- j ι -> ^ CH-CO-OCH,

H ^N CO-CH ₂ -O-CH ₃

CH ₃

(III)

a significant improvement in the fungicidal action occurs. In this case, the increase in effectiveness over a pure, of harmful fungi is based not only on an additive, but on a synergistic effect, which corresponds to the pimple of COIiBY

E = X ₊ Y- I ^

was determined «.

Another advantage is the larger practical range of application of the new combinations, the "B". A simultaneous control of true and false powdery mildew fungi allows »synergistic combinations without phytotoxic damage can be advantageously used against certain tracheomycoses. Danger of the formation of resistant strains is greatly reduced due to the different mode of action of the two components »Thus, the invention Fungizidkombinationen represent a development of the prior

Technique «

The mass ratios of the active H-Alkyldimethylmorpholine (A) and D, Ir-N (2 _r 6-dimethylphenyl) -H '- (2 ^f -methoxyacetyl) alanine methyl ester (B) können.sich in the components within the limits of 250 : 1 to 1: 1, preferably from 100: 1 to 1: 1 move ».

It is particularly advantageous if as H-Alkyldimethylmorpholine (component A) according to DD-PS 140.412 a mixture of. 33 "-alkyl (C ₁₀ -G ^.) -2,6-dimethylmorpholinen and at least 15 % of the positionally isomeric U-alkyl (C ₁₀ -C ₄ ) -2,5-dimethylmorpholine contained *

The new combinations can be used to combat harmful fungi that occur on plants or plant parts. "The systemic properties of both components also protect newly growing parts of plants from fungal attack." The mixtures are effective against phytopathogenic fungi of the following groups: Ascomycetes (eg B Erysiphe- and Sclerotinia Species), oomycetes (especially Phytophthora, Peronospora and

Plasmopara species) and Baaidiomycetes (ζ, Β. Rhizoctonia species) ·

The chemical. Preparation of the U-alkyldiynes thymorpho line (DT 11 64 152, DT 11 98 125, DD HO 041) and of the D, LK- (2, β-dimethylphenyl) -S- (2-methosylacyl) alanine-methyleaters (DD 118 979) is known.

The active compound combinations according to the invention can be converted into the usual formulations, such as solutions. For this purpose, they are dissolved in a known manner with the customary liquid carriers, optionally with the use of surface-active compounds, or dispersed or mixed with solid carrier materials or formulated by other known methods,. The formulations generally contain between 0.1 and 95% by mass of active ingredients, preferably between 5 and 90% by mass. , , _. , The application is usually carried out, for example by dipping, pouring, spraying, spraying or aerosol treatment.

It is also possible to mix other known fungicides, such as ζ, Β, zineb, maneb, mancozeb, folpet, benomyl, carbendazim or fenpropemorph, to the combinations, whereby more than additive effects can also occur. The application rates depend on the specific application purpose and are generally between 0.2 and 1.5 kg / ha.

Exportation Bejieliel_2

Plasmopara on sunflowers

Seedlings of Helianthus annus are infected at the cotyledon stage with Plaamopara halstedii by inoculating a drop of 100 / μl from a zoospore suspension (2.5 x 10 'zoospores / ml) into the axillae of the cotyledons. This Zoosporensuspension is obtained by keeping for 6 hours at 16. ⁰ C in the dark from a Zoosporangiensuspension, Each of the inoculation, the plants are kept at 16 ⁰ C for 12 hours in humid chambers, so that the infection is concerned. Thereafter, the application of the agent is carried out as a 50% emulsion concentrate. Subject of the treatment, the plants in the greenhouse with 10 to 12 h day length (with slight shading) and temperatures between 18 to 23 ⁰ C transferred. The evaluation of the infection success takes place after 12 days in the greenhouse. A second rating after 30 days showed no change. The infections are based on the chlorotic. Ecosystems and the presence of fungal mycelium in the epicotyl tissue.

Table 1: Synergistic effect of a mixture of IT

Dodecyl dimethylmorpholines' (I) U- (2,6-dimethylphenyl) -U- (2 ^r -metho2yacetyl> alanine methyl ester (III) with respect to Plasmopara halstedii

Mean conc. % Infectious Synergistic

/ mg / 1 / inhibition; Effect n. COIBY

I (known) 100 5

I 250 5

III (known) 1 0

III 5. 20 -.

I + III 100 + 1 12 7

I + III 100 + 5 60 36

I + III 250 + 1 37 32

I + III 250 + 5 56 32

' Mixture atis .lT-dodecyl-2,6-dimethylmorpholine (80 %) and. H-dodecyl-2,5-dimethylmorpholine (20 %)

Beis |) iel_2

Plasmopara zoosporangia germ

There are zoosporangia of Plasmopara halstedii washed away from infected plants "The final concentration of the zoosporangia is 2 _r 5 x 10 * V- ml" To determine the Effekt.der means of one die AbtStung of zoosporangia ,, such a zoosporangia suspension, the agent is added and the kill percentage expressed on the untreated control.

Table 2:

Synergistic effect of a 'mixture' of Π-dodecyl-dimethylmorpholines. (I) or H-0 -idene-1'-2, β-dime-thylmorpholine (II) with IS- (2,6-dimethylphenyl) -K ^- - (2 ^f f -methoxyacetyl) älanine methyl ester (III) in germinating zoosporangia of Plasmopara halstedii

medium

Co nz « / mg / 1 /

% of killed zoosporangia

Synergistic rather effect n.COEBY

I 30 6 - II 30 8th - ΙΙΪ 30. 1 - I +111 30 + 30 35 28 II + III 30 + 30 33 24

Mixture of K-dodecyl-2,6-dimethylmorpholine (80%) and N-dodecyl-2,5-dimethylmorpholine (20 %)

Phytophthora agar plate

Phytophthora megasperma var sojae is cultivated in Petri dishes on a medium of age, which is based on Brbssaft (hereditary juice decoction). Inoculation takes place in the middle of the. Petri dish with mycelial slices of 10-day-old cultures .; The funds are added to the Hährmedium in the Petri dishes. Evaluation takes place after 10 days by measuring the colony diameter and by determining the dry weight.

Table 3:

Phonetic synergy effect .One · mixture of Ή- dodecyl dimethylmorpholines' (I) with E '- (2,6-dime thylphenyl) -B ^- - (2' -me thoxyac e tyl) alanine methyl ester (III) on Phytophthora mega cum var * sojae

medium Conc. % Pilzwachstums- Synergistic / Ms / l / hemmunÄ Effect n.COIBY I 10 0 III . 10. 78 .- I + III 10 + 10 90 12

Mixture of .IT-Dodecy 1-2,6-dimethylmorpholine (80%) and N-dodecyl ^^ -dimethylmorpholine (20 %)

Phytophthora on tomato

Solanum lycopersicum - plants of the cultivar "Harzfeuer ^11" are sprayed with the agents individually and in combination until they are dripping wet. * Each time the spray coating is dried, the plants are inoculated with a zoospore suspension of Phytophthora infestans plants a day in a humid chamber at 1-β to 18 ⁰ C and five other location without humidity chamber at the same temperature ,. After that show the typical leaf spots ,, the sheet coverage is a measure of the intensity of infection.

Table 4: Synergistic effect of a mixture of H-dodecyl-dimethylmorpholines (I) or IT-rTridecyl-2, β-dimethylmorpholine (II.) With H- (2,6-dimethyl-phenyl) -ΪΤ- (2 ^f -methoxyacetyl) -alanine methyl ester (III) on Phytophthora infestans on tomatoes

medium

Conc, / mg / 1 /

% Infection inhibition

Synergistis rather effect n «COIBY

I 0.3 .0 - I 3 10 - II 0.3 .0 - II 3 · 10 - III 0.03 20 - III .0,05 .. 55 - I +111 0.3 + 0.03 50 30 II. + III 0.3 + 0.03 50 30 I + .III 3 + 0.03 35 7 II. + III 3- + 0.03 35 7 I +111 0.3 + 0.05 80 25 II. + III 0.3 + 0.05 80 25 I +111 3 + 0.05 80 21 II + III 3 + 0.05 80 21

Mixture of .lT-dodecyl-2,6-dimethylmorpholine (80 %) and H-dodecyl-2,5-dimethylmorpholine (20 %)

Phytophthora on tomato

Solanum lycopersicum - plants of the variety "Tamina" in the 4- leaf stage.with the means individually and in combination dripping wet. "sprayed" After the spray coating has dried on, the plants are inoculated with a zoospore suspension of Phytophthora infestans. "The plants then remain in a humid chamber at 16-18 ⁰ C for one day and at the same temperature for another five days without a moist chamber »Afterwards, the typical leaf spots appear, whose leaf coverage is a measure of the infection intensity.

Table 5: Synergistic effect of a mixture of 3SV. Dodecyl-dimethylmorpholinen ^ (I) with F- (2,6-dimethylphenyl) -U- (2'-methoxyacetyl) alanine methyl ester (III) on Phytophthora infestans on tomatoes

medium Konz · % Infection synergistic / M / l / inhibition Effect n.COLBY I 0.1 .5 - I 2.5. 11 - III 0.01 11 - III .055 · 25 .- I + III 0.1 + 0, 01 33 18 I + III 2.5 + 0, 05 56 23

Mixture of IT-dodecyl-2,6-dimethylmorpholine (80 %) and IT-dodecyl-2,5-dimethylmorpholine (20 %)

Beisp_iel_6

Mycelium growth test with Pythium spec.

The active ingredients are added in graded concentrations to the liquefied agar medium, which is then poured into sterile Petri dishes. After solidification of the agar takes place, the inoculation of the medium with the test fungus. Each 7-day incubation. Radial mycelial growth of the fungal colony was determined.

Table 6: Synergistic effect of a mixture of H-. Dodecyl dimethylmorpholines. (I) with F- (2,6-dimethylphenyl) -U- (2-methosylacyl) -alanine methyl ester (III) on Pythium spec.

medium

Konz'e% läycelwachstums- / mg / 1 / inhibition

Synergist is before: effect η.COEBY

I III 2500 0 - I III 5000 0 - III , 50.. , 0 , - I + 2500 + 50 48 48 I + 5000 + 50 70 70

Mixture of lT-dodecyl-2,6-dimethylmorpholine (80 %) and H-dodecyl-2,5-dimethylmorpholine (20 %)

Example J7

Pesticide resistance in Plasmopara

Boy. Plants of Helianthus annus are infected with Plasmopara halstedii, adding the shoot tip of the plants in the plant. Two-leaf stage, a drop of 100 / ul of a Zoosprangiensuspension.Es added. The zoosporangia concentration is 2.5 s 10 ^ zoosporangia / ml. 2, 5 σ 10 ^ Zoosporangia per plant "The application of the funds takes place as

75 % complete emulsion concentrate "The evaluation of the infection intensity and the frequency of the fungicide resistance is carried out after 12 days.

100 mg / l of III alone does not provide complete protection against infection but only a 99 % protective effect. Because of the residual infection, the frequency of fungicide resistance is not "determinable."

1000 mg / l of III cause complete protection against infection, but also fungicide resistance was observed at a frequency of 2 χ 10 "...

If 100 mg / l of III are administered with 500 mg / l of I, 100% protection effect occurs and it was at. Experimental range of 1.9 x 10 'S. porangia (~ 750 plants) no resistance is observed, so it is concluded that the probability of the occurrence of fungicide resistance in the combination of I and III in the ratio 5: 1 more than 10. times lower than in the case of application of III alone, but could not be determined for practical trial size It is crucial that the combination of I and III reduces the frequency of fungicide resistance by a multiple.

Table 7:

Frequency of emergence of resistance in application of. .H- (2, β-dimethylphenyl) -Έ- (2'-methoxyacetyl) alanine ethyl ester (III). and in a mixture of U-dodecyl-dimethylmorpholines' (I) in Plasmopara halstedii on Helianthus annus

Kittel Conc. Protective effect

/ mg / 1 /% de r.Pflanzen

Frequency of resistance

III 1000 100 2 χ -10 ~ ^ö III .100 .99 not definable I 5000 100 0 I 1000 85 not definable I. , 500th. .55 not definable I + III 500 + 100 100 <1,9 χ 10 " ⁷

Mixture of lT-Ddecyl-2,6-dimethylmorpholine (80 %) and U-Dodecyl-2,5-dimethylmorpholine (20 %)

Claims (1)

Invention claim ft · · 1. Pungicide combinations, characterized in that they are active as a mixture of (A) & Al] qrl-2,6 <-dimethylmorpholines of the general <. Formula 1 or a combination with their positionally isomeric F-alkyl-2,5-dimethylmorpholinen of the general formula II 3 s , 3 Έ - R 0 UR H ₃ C GH ₃ in which R is long-chain alkyl (C ₁₀ -C ₁₈ , straight, branched or cyclic), (B) D, L-IT- (2,6-dimethylphenyl) -ir- (2'-methoxyacetyl) alanine methyl ester (III) CO-CH ₂ -O-CH- CH ₃ (III) contain" ^ o -H- 2o Fungizidkombinationen after item 1 _r, characterized in that they are the components A and B in a mass. ratio of 100: 1 to 1: 1 included ·
3o Use of funds according to item 1 ,. in-DA. , in that they are used in plant protection. 4 Method of combating fungi, characterized in that a combination of active substances is used in accordance with. Point 1 on fungi or their habitat act.