IE47942B1 - Fungicidal formulations - Google Patents

Description

This invention re’ates to fungicidal formulations and to methods of treating fungal infections of cultivated plants.

According to one aspect of the present invention, there provided a fungicidal formulation comprising as a first mngicida lly active ingredient a pyrimidine of formula :- where X is chlorine or fluorine, and as a second fungicidally active ingredient a compound of formula:47942 0 I I C_H NHCNHCCCN 2 5 # N0CH3 11(b) where R is fur-2-yl or -CH^OCH^, associated with one or more inert, non-phytotoxic carrier(s) therefor.

All of the aforementioned compounds are known compounds and may be prepared by methods well-defined in the literature.

The pyrimidines of formula 1 are described in Patent Specification No. 32255 the alanine derivatives of formula II(a' in Patent Specification No. 41140 and Belgian Patent Specification No. 827,6/1 and the urea of formula 11(b) in U.K. Patent Specification No. 1,470,740.

The combinations of active ingredients defined in the above formulation are novel and have been found to be surprisingly effective in controlling or combatting fungal infections of cultivated plants. They are of value in the treatment of a wide range of cultivated crops susceptible to fungal attack, such as for example cereals and beans, and in particular crops susceptible to powdery and downy mildew, as well as late blight, i.e. crops such as grapes, cucurbits and tobacco susceptible to attack by microorganisms of Nomycestes and Erysiphales species.

According to a second aspect of the invention, there is provided a method of treating fungal infections of plants especially grapes which comprises applying to said plants a fungicidally effective amount of a fungicidal formulation as 7 9 4 2 defined above.

In the aforesaid method, the formulation can be applied b/ foliar application or soil drench, depending on the crop being treated, at any time after crop emergence until havest5 ing taxes place. The amount and frequency of application will be determined by fhe severity or expected severity of the fungal disease and, as is well known to those skilled in the art, by the age and condition of the crop. However, it is a feature of the invention and a particular advantage obtained therefrom that a reduced frequency of treatment, for example only once every 2 to 3 weeks to control grape mildew infections, may be effectively employed, thus achieving a valuable reduction in labour costs.

The preferred pyrimidine for use in foliar application ,= for instance in grape treatment is that in which X is chlorine. However, when application of the combination of the invention is to be effected by means of a soil drench it has been found that the pyrimidine of formula 1 in which X is fluorine is particularly efficacious.

As stated above, formulations of this invention are applied by foliar application or by soil drench. In soil drenches, the compound of formula 1 is preferably applied in an amount of from 50 to 500 g per hectare, whereas the compounds of formula 11 (a) are preferably applied in amounts of from 500 to 3000 g per hectare. Thus the ratio of compounds of formula to compounds of formula 11(a) in such formulations may preferably range from 1:1 to 1:60 by weight.

When foliar application is utilised the compound of formula 1 is preferably applied at a rate of from 10 to 100 g per hectare. The compound of formula 11(a) is preferably applied at a rate of from 100 to 2,500 g per hectare. In such circumstances, the compound of formula 11(b) is preferably applied at a rate of from 50 to 500 g/hectare. Accordingly, the ratio of compounds of formula 1 to compounds of formula 11 in formulations applied by foliar application is preferably from 5:1 to 1:250 by weight.

The formula 11(b) compound is preferably used in combination with a further fungicide, such as for example zineb or mancozeb, and as specified in U.K. Patent Specification No. 1,470,740. It should be noted that such further fungicides are used at approximately half their normal rate and that the compound of formula 11(b) is not compatible with compounds which increase alkalinity.

In order to simply manufacture, storage and transport, the combinations of the formulae 1 and 11 compounds will be normally produced in concentrate form intended for dilution in water to the degree necessary to enable the above mentioned application rates to be easily achieved. Such concentrated formulations may contain from 0.5 to 50%, preferably 5 to 90% by weight of active ingredients associated with one or more inert non-phytotoxic carrier(s) therefore. Such formulations will usually be in the form of a wettable powder or dust, aqueous suspension, emulsifiable concentrate or granules. The concentrate formulations are intended for appropriate dilution with water prior to use. This formation of an aqueous dispersion can be carried out in conventional spray tanks suitable for the purpose. It is to be clearly understood that the diluted formulations so produced are formulations in accordance with the invention in which one or all of the inert non-phytotoxic carrier(s) is water. 47943 Wettable powders or dusts comprise an intimate mixture of the active ingredients, one or more inert carriers and appropriate surfactants. The inert carrier may be chosen from the attapulgite clays, the montmorillonite clays, the diatomaceous earths, kaolins, micas, talcs and purified silicates. Effective surfactants may be found among the sulfonated lignins, the naphthalene sulfonates and condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzene sulfonates, the alkyl sulfates and non-ionic surfac10 tants such as ethylene oxide adducts of phenol. Illustrative of wettable powders falling within the scope of the invention are those having the following composition: Wettable Powders % by weight Formula 1 compound 1 to 10 Formula 11 compound 5 to 60 Surfactant(s) 0 to 10 Dispersing Agent 0 to 10 Anticaking agent 0 to 15 Inert carrier (s) to 100 The following non-limitative Examples will serve to further illustrate the invention.

The compound of formula 1 in which X is chlorine is known as fenarimol, whilst the related compound in which X is fluorine is known as nuarimol. In the Examples below the compound of formula 11(a) in which R is fur-2-yl is represented by the letter A, the formula 11(a) compound in which R is -CH^OCH^ by B and the formula 11(b) compound by C EXAMPLES 1 to 10 The following wettable powders were prepared:- 7 - (1) % by weight Compound A 25 Fenarimol 5.0 Sodium lauryl sulphate 4.0 5 Sodium lignin sulphonate 3.0 Precipitaled silica 8.0 kaolin clay to 100.0 (2) % by weight Compound A 50.0 10 Nuarimol 2.5 Sodium dioctyl sulphosuccinate 5.0 Sulphonated lignin 2.0 Diatomaceous earth to 100.0 (3) % by weight 15 Compound B 40.0 Fenarimol 4.0 Ethoxylated alkyl phenol 3.0 Sodium lignin sulphonate 5.0 Hydrated sodium silicoaluminate 4.0 20 Talc to 100.0 (4) % by weight Nuarimol 2.0 Compound B 40.0 25 Sodium aIkylnaphthalene sulphonate 8.0 Silica 3.0 Kaolin to 100.0 7 9 4 2 (51 Compound C Fenarimol Sodium alkyl ether sulphate Sodium lignin sulphonate Silica Attapulgite to % by weight 36.0 6.0 4.0 3.0 7.0 100.0 (61 Compound C Fenarimol Zineb Sodium salt of condensed naphthalene sulphonic acids Sodium lignin sulphonate Hydrated sodium silicoaluminate Montmorillonite to % by weight 6.0 1.0 50.0 3.0 4.0 8.0 100.0 (7) Compound C Fenarimol Mancozeb Sulphite lye powder Sodium lauryl sulphate Silica Kaolin to % by weight 3.0 0.5 36.0 2.0 .0 6.0 100.0 In each of the above Examples, the active ingredients were carefully blended with the specified excipients in conventional mixing equipment. The blend was then further milled in a fluid energy mill to a size range of from 1 to 10 microns and finally the mixture was reblended and deaerated prior to being packaged. 47843 - 9 The formulations described in Examples 1, 3 and 5 to 7 are intended for use in foliar application whereas the formulations of Examples 2 and 4 are of value as soil drenches.

EXAMPLE 8 The following Example illustrates the typical synergistic activity to be observed when combinations of the inventions are employed for control of fungal organisms.

Solutions of fenarimol in water were prepared at a concentration of 10 and 20 parts per million and solutions of compound B at a concentration of 50 and 100 parts per million. They were applied separately and together to 11 day old Pinto bean plants. A single treatment consisted in spraying 3 pots, each pot containing two plants.

When the plants had dried they were inoculated with a suspension of spores of bean leaf rust and incubated for 48 hours in a cool moist chamber.

The percentage control of the disease was then noted as follows :- FENARIMOL COMPOUND B Percentage control by combination of fenarimol and compound B (concentrate p.p.m.) (percentage disease control) (concentrate p.p.m.) (percentage disease control) 10 35 50 6 62 10 35 100 29 85 20 77 50 6 95 20 77 100 29 96 When analysed by the well-known Colby equation (see Weeds, 15, 20-22 (1967) the above results clearly showed that under the conditions of the test, this mixture of the invention demonstrated synergism.

Claims (11)

1. CLAIMS :1. A fungicidal formulation comprising as a first fungicidally active ingredient a pyrimidine of fqrmula:- where X is chlorine active ingredient a or fluorine, and as compound of formula a second fungicidally II II C_HNHCNHCCCN 2 5 I N0CH 3 11(b) where R is fur-

2. -yl or -CH^OCH^, associated with one or more inert, non-phytotoxic carrier (s) therefor. 10 2. A fungicidal formulation according to claim 1 comprising a compound of formula 1 and a compound of formula 11(a). 4 7 9 4 2 - 11

3. A fungicidal formulation according to claim 1 comprising a compound of formula 1 and a compound of formula 11(b).

4. A fungicidal formulation according to any of the preceding claims in which the first and second fungicidally active 5. Ingredients are present in the ratio range of from 5:1 to 1:250 by weight.

5. A method of treating fungal infections of plants which comprises applying to said plants a fungicidally effective amount of a fungicidal formulation as claimed in any of claims 10 1 to 4.

6. A method according to claim 5 which comprises applying the formulation to grapes.

7. A method according to either of claims 5 and 6 in which the fungicidal formulation is applied as a foliar spray. 15

8. A method according to claim 7 in which the compounds 1 are applied at a rate of from 10 to 100 g per hectare.

9. A method according to either of claims 7 and 8 in which the compound of formula 11(a) is applied at a rate of from 1OO to 2,500 g per hectare. 20

10. A method according to any of claims 9 to 12 in which the compound of formula 11(b) is applied at a rate of from 50 to 500 g per hectare.

11. A fungicidal formulation according to claim 1 substantially as described in any of the Examples,