HU182518B - Synthetic fungicide derivatives - Google Patents

Abstract

Fungicidal formulations are described which comprise as a first fungicidally active ingredient a pyrimidine of formula:- <IMAGE> where X is chlorine or fluorine, and as a second fungicidally active ingredient a compound of formula: <IMAGE> where R is fur-2-yl or -CH2OCH3, associated with one or more inert, non-phytotoxic carrier(s) therefor. Fungicidal methods employing such formulations are also described.

Description

FIELD OF THE INVENTION The present invention relates to synergistic fungicidal compositions for treating fungal diseases in crop plants.

More particularly, the present invention relates to a synergistic fungicidal composition comprising as active ingredient a pyrimidine derivative of the formula (I) in which X is chlorine or fluorine and a combination of the compound (IIa) or the compound (IIb). inert, non-phytotoxic vehicle and optionally other conventional additives.

All of the aforementioned compounds are known and can be prepared by methods well described in the literature. The pyrimidine derivatives of formula (I) are disclosed in British Patent No. 1,218,623, the alanine compound of formula (Ha) in British Patent Nos. 1,448,810 and Belgian Patent 827,671, and the urea derivative of formula (IIb) in 1,470. British Patent 740.

However, the combination of the known known fungicidal compounds as described above is novel and surprisingly effective in the treatment and cure of fungal infections in crop plants. The combination fungicidal composition of the present invention protects a wide variety of crop plants which are susceptible to fungal infections and can be used to treat crops and beans, especially plants that are susceptible to powdery mildew and moth, such as grapes, pumpkins and tobacco. The exemplified plants may be infected by microorganisms belonging to the species Domycetes and Erysiphales.

In addition to the description of the compositions, the methods of using the compositions of the invention to treat fungal diseases of crop plants, particularly grapes, are also provided.

The treatment can be done by leaf or by thorough irrigation of the soil, depending on the crop to be treated, at any time between emergence and harvest. The amount employed and the frequency of application will depend on the severity or the probable severity of the fungal disease and on the age and condition of the plant to be treated and will not be a problem for one of ordinary skill in the art. It is to be emphasized that the compositions of the present invention are relatively rare in the treatment of grape powdery mildew infection, which can be adequately cured or prevented by treatment every two to three weeks, which results in significant labor and cost savings.

Particularly in the case of leaves, for example in the case of grapes, the pyrimidine derivative containing a chlorine atom as the X substituent proved to be effective. If, however, the compositions of the present invention are to be used for irrigation of the soil, they are found to be particularly effective if they contain a pyrimidine derivative containing a fluorine atom as the X substituent.

As mentioned above, the compositions of the invention may be used to treat leaves or to impregnate the soil. When applied by irrigation of the soil, the application rate of the compounds of the formula I is preferably 50-500 g / ha, while the application of the formula Ha is preferably 500-3000 g / ha. Thus, the ratio of the compound of formula (I) to the compound of formula (IIa) in these compositions is preferably from 1: 1 to 1:60 (w / w).

When treating the leaves of plants with the compositions, the compounds of the formula I are preferably used in an amount of 10 to 100 g. The application of the compound of formula (IIa) is preferably applied in an amount of 100 to 2500 g / ha. Under these conditions, the compound of formula IIb is preferably applied in an amount of 50-500 g / ha. Accordingly, the ratio of the compounds represented by the formulas I and II to the treatment of leaves is 2: 1-1: 250 (w / w).

For ease of preparation, storage and transport, the compounds of formula (I) and (II) are preferably formulated into the corresponding compositions of the present invention by preparing a concentrated form which is subsequently diluted with water to a concentration that allows the amount of active ingredient can be easily adjusted. Concentrated preparations contain from 0.005% to 75% by weight, preferably from 5% to 75% by weight, of an active ingredient in combination with one or more inert, non-phytotoxic carriers and optionally other additives. The formulations may generally be formulated as wettable powders, aqueous suspensions, emulsifiable concentrates or granular formulations. Concentrated preparations should be diluted with water to the desired concentration before use. These aqueous dispersions can be prepared in conventional spray containers suitable for this purpose. It is to be emphasized that the diluted compositions thus prepared are also within the scope of the invention. A common feature is that they contain one or all inert, non-phytotoxic vehicle water.

Wettable powders are intimate admixtures of the active compounds and one or more carriers and suitable surfactants. Attapulgite clays, montmorillonite clays, diatomaceous earth, kaolin, mica, talc and purified silicates may be used as inert carriers. Active surfactants include sulfonated lignins, naphthalene sulfonates and condensed naphthalene sulfonates, alkyl succinates, alkyl benzene sulfonates, alkyl sulfates; in addition, ethylene oxide adducts of nonionic surfactants such as phenol. For example, the composition of the wettable powders of the present invention may range from:

Wettable powders by weight Compound of Formula I 1-10 Compound of Formula II 5-60 Surfactants 0-10 Dispersive Agents 0-10 Antifouling Agent up to 100

As used hereinbefore and hereinafter, the compounds of formula (II) shall be understood to mean the compounds of formula (IIa) and (IIb).

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The compound of formula (I) wherein X is chlorine is known as fenarimol, while the corresponding compound containing X as fluorine is known as nuarimol.

Further details of our invention are as follows

examples. Example 1 weight% Compound of Formula IIa 40.0 fenarimol 4.0 ethoxylated alkyl phenol 3.0 Sodium ligninsulfonate 5.0 hydrated sodium silicoaluminate 4.0 talc 100.0

The above active ingredients are thoroughly mixed with the indicated additives in a conventional mixing apparatus. The resulting mixture was further milled in a fluidization mill to a particle size of 1-10 microns, then the mixture was again mixed and de-aerated prior to packaging.

The wettable powder formulations provided in the following examples are also prepared by the above method.

Example 2% by weight nuarimol 2.0 Compound IIa 40.0 Sodium alkyl naphthalenesulfonate 8.0 Silica 3.0 up to 100.0 kaolin

Example 3 Compound IIb% by weight 36.0 fenarimol 6.0 sodium alkyl ether sulfate 4.0 sodium lignin sulfonate 3.0 silica 7.0 attapulgite up to 100.0

Example 4 Fenarimol 5.0% Ha Compound 70.0 Sodium Alkyl Naphthalene Sulfonate 3.0 Sodium Lignin Sulfonate 5.0 Silica 5.0 to 100.0

Example 5 weight% nuarimol 5.0 Compound IIb 70.0 Sodium lauryl sulfate 4.0 Sodium ligninsulfonate 5.0 hydrated sodium silicoaluminate 6.0 talc 100.0 Example 6 weight% nuarimol 1.0 Compound of Formula IIa 10.0 sodium alkyl tersulfate 4.0 Sodium ligninsulfonate 6.0 precipitated silica 15.0 kaolin 100.0

The formulations in Examples 1, 3 and 4 are useful for treating leaves, while the formulations in Examples 2, 5 and 6 are effective in watering the soil.

Example A- (2-Chlorophenyl) -a- (4-chlorophenyl) (pyrimidin-5-yl) methanol (fenarimol) and N- (2,6-dimethylphenyl) -N- Synergistic effect of combination of methoxyacetyl-dl-alanine methyl ester (compound of formula Ha)

Aqueous solutions of fenarimol and 20 ppm and 50 and 100 ppm of compound (IIa) were prepared. Thereafter, 11-day-old Pinto bean plants were treated individually and in combination with the solutions. In our experiments, one treatment consists of spraying three pots containing 2-2 plants each.

After drying, the plants are inoculated with a suspension of rust spores of bean leaves and incubated for 48 hours in a cold, moist chamber.

The percent effect of the formulation is compared in the following table with the percent effect observed for the two components separately:

agent concentration rationality (Ppm) Antifungal effect (%) fenarimol 10 35 20 77 Compound of Formula IIa 50 6 100 29 Fenarimol + (Ha) 1O 50 62 compound of formula 10 * 100 85 20 50 95 20100 96

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Using the well-known Colby equation (Weeds, 15, 20 (1967)) to evaluate the experimental results, it can be clearly established that the test mixture exhibits synergism under the experimental conditions.

Synergism is demonstrated by the fact that the measured antifungal effect is greater than the calculated theoretical value.

Repeating the above experiment with Pythium ultimum fungus gives the following results:

Example B)

Fenarimol and N- [2-cyano-2- (methoxyimino) - j

Synergistic effect of the combination of -acetyl] -N'-ethylurea (compound of formula (IIb)) potato dextrose agar containing ppm of fenarimol and 20 ppm of compound of formula (IIb) is prepared. The above preparations or their respective mixtures are poured into a 15 x 100 mm petri dish and allowed to freeze.

Inoculate the medium by placing a 6 mm-20 agar disk containing Aphanomyces euteiches fungal mycelium in the center of the Petri dish.

The disk is positioned with the mycelial surface facing up. The Petri dishes were incubated at 26 ° C.

The antifungal activity was determined by comparing the radial growth of the culture on the surface of the Petri dish containing the fungicidal agent or mixture with that of the control (without fungicidal compound (s)). ³⁰

agent concentration rationality (Ppm) Antifungal effect (%) fenarimol 1 37 Compound IIb 20 23 Fenarimol + compound of the formula IIb 1 + 20 66

From the individual antifungal activity of the fungicidal compounds, the theoretical antifungal activity of the mixture is calculated using the known Colby equation.

agent concentration rationality (Ppm) Antifungal effect (%) fenarimol 20 69 Compound IIb 10 42 Fenarimol + compound of the formula IIb 20 + 10 87

The test mixture also shows a synergistic effect against the above fungal species.

Claims (3)

Patent claims: Claims 1. A synergistic fungicidal composition comprising biologically active agents and solid carrier (s), preferably natural mineral material (s), and surfactant (s), preferably ionic and / or nonionic emulsifier (s). , characterized in that the active ingredient is 0.005-75% by weight of a pyrimidine derivative of formula I wherein X is chlorine or fluorine and an alanine derivative of formula IIa or a urea derivative of formula IIb: 1: 0.5- It contains a combination of 1: 20 by weight. 2. The fungicidal composition of claim 1, wherein the active ingredient is a combination of a compound of formula (I) wherein X is as defined in claim 1 and a compound of formula (Ha). 3. The fungicidal composition of claim 1 wherein the active ingredient is a combination of a compound of formula I wherein X is as defined in claim 1 and a compound of formula IIb.