JPH027283B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel fungicidal compositions based on iprodione.

Iprodione is the well-known name for an agricultural fungicide known by the chemical name 1-isopropylcarbamoyl-3-(3,5-diclophenyl)-hydantoin. This fungicide has excellent activity against phytomycosis, especially grape botrytis.

Hitherto, this active substance has been commercially available primarily in the form of a wet powder. This formulation has the disadvantage that fines are dispersed into the atmosphere during handling, during bagging of the powder, or during dilution of the wet powder with water during slurry preparation. Additionally, this formulation is washed off the surface of leaves and seeds during heavy rains.

The aim of the invention is to overcome these drawbacks. Thus, the object of the present invention relates to an agricultural fungicidal composition based on iprodione, which composition comprises, by weight, a active substance based on iprodione from 20 to 40
% and b an oil with a hydrophilic/lipophilic balance (HLB) value of 8 to 12 on the HLB scale, preferably 10 to 11, as required for the preparation of "oil-in-water" emulsions to iprodione. an "oil-in-water" emulsion containing 160% by weight; c. an ethylene oxide/fatty alcohol condensate ethoxylated fatty alcohol type nonionic emulsifier;
0.1-2% and d as required, almost neutral hydrophilic silica 0.5-2%
2.5%, with the remainder consisting of water and usual additives to make a total of 100%.

The composition of the present invention is a concentrated suspension of iprodione in an oil-in-water emulsion. These fluid formulations are often referred to in practice as "fluid pastes",
called "creams" or "flowables".

The active substance of these compositions is based on iprodione and is in the form of solid particles, the solid particles having an average diameter of less than 10μ, preferably from 1 to 5μ.

The active substances of these suspensions include, in addition to iprodione, other active substances, such as carbendazim, benomyl or methylthiophanate, or copper-based compounds, metallic ethylene-
Bis-dithiocarbamates, such as maneb, zineb or mancozeb, or phthalimide derivatives, such as captan, captafur or fluorpept, may be included.

However, other mixtures containing iprodione in combination with other fungicides can also be formulated according to the invention.

The oil that can be used in the compositions of the present invention can be of various types, provided that it is capable of dissolving 1 to 5 g of iprodione per oil at room temperature, and that its hydrophilic/lipophilic balance (HLB ) is a value of 8 to 12 on the HLB scale required for the preparation of "oil-in-water" emulsions, preferably
shall have a value of 10 to 11, preferably further
It shall have a viscosity of 20-30 cst. Hydrophilic/
The lipophilic balance is defined and determined according to Bade van Valkenburg's "Cermicidal Formulations" published by Marcel Detzker & Co., New York (1973).

These oils are commonly called white oils, for example;
It may be a mineral oil, such as refined petroleum, with a boiling point range of 300-400° C. at atmospheric pressure and preferably a high paraffinic hydrocarbon content with a minimum proportion of 92% of non-sulfonatable substances. It is also possible to use certain vegetable oils, such as peanut oil, corn germ oil or rapeseed oil, whose hydrophilic/lipophilic balance has a value within the above range.

Other important components of the compositions according to the invention are emulsifiers, in particular of the ethylene oxide/fatty alcohol condensate type, which contain one or more linear or branched C ₁₂ -C ₁₄ , preferably C ₁₃
aliphatic alcohol and 8 to 12 moles, preferably 9 to 12 moles;
A condensate with 10 moles of ethylene oxide, which acts as a dispersing-wetting agent for iprodione and as an emulsifying agent for two-component "oil-water" systems, thereby forming a concentrated suspension of iprodione in oil-in-water emulsions. It gives things stability.

In some cases, if it is desired to reduce the amount of oil in order to reduce any possible phytotoxicity without diminishing the biological properties of the formulation, 0.5 to
It may be advantageous to add 2.5% by weight of preferably approximately neutral hydrophilic silica to the composition. In this specification, the term "hydrophilic silica" preferably has a silica content of 200 to 300
This is understood to mean synthetic silicas such as ultrafine hydrated precipitated silicas with high specific surface areas of the order of m ² /g. This type of silica is nearly neutral;
That is, the pH in an aqueous suspension is 7±0.5.
In practice, neutral or slightly acidic silicas are preferred.

The compositions of the invention may further contain viscosity modifiers (usually 0.05 to 0.1% by weight) of the heteropolysaccharide type resulting from the fermentation of carbohydrates by microorganisms of the polysaccharide type, in particular of the Xanthomonas type, preferably ethylene oxide/ polyarylphenols, especially dispersing-plastic agents of the polystyrylphenol condensate type (usually 0.5 to 2.5% by weight), antifreeze agents such as ethylene glycol or propylene glycol (usually 5 to 10% by weight);
It may also contain customary auxiliaries such as defoamers, such as silicone oil emulsions (usually 0.2-0.6% by weight) and preservatives, such as formaldehyde, for microbial growth (usually 0.1-0.2% by weight). can.

The compositions of the invention can be manufactured, for example, in three steps.

The first stage is in a tank equipped with strong stirring means.
"Oil-in-water type" is created by flowing oil into water containing other water-soluble additives and emulsifiers if necessary.
It consists of preparing an emulsion.

In the second step, iprodione is dispersed as a fine powder into the oil emulsion with continuous stirring. The resulting suspension is then re-refined in a mill of the ball mill type, such as a DYNO-MILL.

In the third and final step, a viscosity modifier of the heteropolysaccharide type is added to a preservative (40% formaldehyde).
aqueous solution) and/or dispersed in a small amount of water containing neutral hydrophilic silica. This dispersion is added to the above iprodione suspension.

The iprodione oil-based composition of the present invention has the advantage of being a fluid composition that is easier to handle than wet powders, and it also has the advantage of being a fluid composition that is easier to handle than wet powders. Botrytis (Botrytis)
When applying a spray treatment to eradicate cinerea),
It has the advantage of showing improved bactericidal effect and not showing phytotoxicity.

The following examples are provided to illustrate the compositions of the invention and their valuable biological properties, but the invention is not limited thereto.

Example 1 A thick oily suspension was prepared with the following weight % composition: -25.0 iprodione with a particle size of around 2μ -containing more than 70% paraffin and 10.5 hydrophilic/
Paraffinic mineral oil having a lipophilic balance value and capable of solubilizing 1 g of iprodione per oil.
33.0 - Emulsifiers based on condensates of 9 to 10 moles of ethylene oxide and synthetic C ₁₃ alcohols 0.8 - Ethylene oxide/polystyrylphenol condensates phosphates 2.5 - Ethylene oxide/polyalkylphenol condensates
0.5 - Ethylene glycol 5.0 - Heteropolysaccharide (Rhodopol23) 0.065 - Formaldehyde (40% aqueous solution) 0.15 - Silicone oil emulsion 0.5 - Water Amount to bring the total volume to 100 First, water, glycol, and silicone emulsion act as an emulsifier. and surfactant were mixed in a bath. The mixture was stirred until completely dispersed and then the oil was poured into it.

Iprodione was then added with continuous stirring. An emulsion was thus obtained which was ground in a dinormil to obtain a thick suspension of iprodione.

In the third and final step, a viscosity modifier (heteropolysaccharide) predispersed in a small amount of water containing a preservative (40% formaldehyde solution) is mixed into the suspension of iprodione to finally improve the flowability. A paste or thick dispersion was obtained which could be used.

Example 2 By the procedure of Example 1, a thick oily suspension was prepared with the following weight % composition: - Iprodione 30.0 - Containing more than 70% paraffin and having a hydrophilic/lipophilic balance value of 10. 1.2 per katsu oil
mineral oil that dissolves g of iprodione 20.0 - ethylene glycol 5.0 - condensate of 8 to 10 moles of ethylene oxide with synthetic C ₁₃ alcohol 0.8 - acid phosphate of ethylene oxide/polystyrylphenol condensate 1.2 - silicone oil emulsion 0.5 - synthesis Neutral hydrophilic silica (BET specific surface area: 200
m ² /g) 2.0 - Water Amount to bring the total volume to 100 Example 3 A thick oily suspension was prepared according to the procedure of Example 1 with the following weight % composition: - Iprodione 34.5 - More than 70% paraffin Mineral oil having a hydrophilic/lipophilic balance of 11 and dissolving iprodione per oil 20.0 - Ethylene glycol 5.0 - Condensate of 9 to 10 moles of ethylene oxide with synthetic C ₁₃ alcohol 1.0 - Ethylene oxide/ Acid phosphate of polyarylphenol condensate 1.5 - Silicone oil emulsion 0.5 - Neutral hydrophilic precipitated silica (BET specific surface area:
300 m ² /g) 1.25 - Water Amount to bring the total volume to 100 Example 4 By the procedure of Example 1, a thick oily suspension was prepared with the following wt% composition: - Iprodione 37.5 - 3.5 g of Iprodione/1. 20.0 - Ethylene glycol 5.0 - Condensate of 9-10 moles of ethylene oxide with synthetic C ₁₃ alcohol 1.0 - Phosphate of ethylene oxide/polystyrylphenol condensate 2.0 - Silicone oil emulsion 0.5 - Medium Hydrophilic Silica 1.0 - Water Amounts to bring the total volume to 10 Example 5 By the procedure of Example 1, a thick oily suspension was prepared with the following weight percentage composition: - Iprodione 26.0 - Contains more than 70% paraffin and 10.5
Paraffinic mineral oil with HLB value and solubilizing 4.5 g of iprodione per 32.2 - Emulsifier based on the condensate of 9 to 10 mol of ethylene oxide and synthetic C ₁₃ alcohol 0.8 - Ethylene oxide polystyrylphenol Condensed phosphate 2.5 - ethylene oxide polyalkylphenol condensate
0.5 - Propylene glycol 5.0 - Heteropolysaccharide (Rhodopol 23) 0.65 - Formaldehyde (40% aqueous solution) 1.5 - Water Amount to bring the total volume to 100 Example 6 According to the procedure of Example 1, Iprodione with the following weight % composition and was combined with the other active ingredients, namely carbendazim, and the auxiliaries were the same as in Example 5: - iprodione 18.0 - carbendazim 9.5 - paraffinic mineral oil 28.0 - 9 to 10 mol Emulsifiers based on condensates of ethylene oxide and synthetic _C13 alcohols 0.8 - Ethylene oxide polystyrylphenol condensate phosphate 2.5 - Ethylene oxide polyalkyl phenol condensates
0.5 - Propylene glycol 5.0 - Heteropolysaccharide (Rhodopol 23) 1.3 - Formaldehyde (40% aqueous solution) 3.0 - Water Amount to bring the total amount to 100 Example 7 Botrytis cinerea (grape)
These tests were carried out by applying the same amount per hectare of the composition of Example 1 and, for comparative purposes, a commercially available wettable powder containing 50% by weight of iprodione, according to the following treatment program: A vine area of 50 m ² was carried out: First treatment: When the corolla falls, it is carried out to remove the dry flower parts that may remain on the seeds and to protect the stems.

Second treatment: Carry out before the tuft is filled, ie while the stems can still be reached by spraying, in order to protect the stems from early attack of rot.

Third treatment: This is carried out at the beginning of ripening, when the fruit becomes susceptible to attack by Botrytis, which causes gray rot in grapes.

Fourth treatment: Approximately 3 weeks before the time of grape harvest, in order to ensure that the harvest is in a healthy state, at a time when physiological and climatic conditions are very favorable for the growth of mold.

These treatments were carried out by pneumatic spraying at low volumes/ha, i.e. 100-300 per hectare, directed to the tuft area (local application) and at a treatment dose of 750 g of active substance per hectare. .

Botrytis contamination occurred naturally during the humid September and October period due to frequent night fogs.

Of course, some areas were left untreated to serve as comparisons.

At harvest, the degree of fruit rot was assessed in comparison to a control area with contaminated end-treatment grapes.

Under these conditions it was observed that: - the areas of the untreated comparison grapes were eroded to an intensity of 41%, and the commercial composition of iprodione as a 50% wet powder had an average protective effect of 34%; , whereas the composition of Example 1 applied at the same dose of active substance/ha showed a protective effect of 61%.

Furthermore, the composition of Example 1 was found to be entirely selective for grapes.

Example 8 Field fungicide trials of Botrytis cinerea on legumes These trials were conducted using the composition of Example 1 and for comparative purposes a commercially available wet powder containing 50% by weight iprodione at the same dosage per hectare according to the following program: The application is carried out on a ^5m2 area planted with legumes, each treatment is applied at a low volume of 750 m2 per hectare (100-300 per hectare).
It was carried out by pneumatic spraying at a dose of g/ha.

First treatment: at the beginning of flowering Second treatment: at the end of flowering Some areas were left untreated to serve as comparisons.

Pollution occurred naturally.

Under these conditions, at harvest time it was found that: - the control area was eroded to an extent of approximately 27%; - the area treated with iprodione as a wet powder was eroded to an extent of approximately 15%; - the main The area treated with iprodione formulated according to the invention was eroded to the extent of only 4.5%.

Example 9 Rainfall Tolerance Test Tomato plants of Eurocross B variety with a height of 15 cm were sprayed with 50% by weight of iprodione as a commercially available wet powder and with iprodione prepared in the same manner as in Example 1. The two formulations were administered at the same dosage of 375 g of active substance per 1000. Leaves were kept dry. Several plants were then subjected to different levels of artificial rainfall using a rainfall-simulating device. Leaf samples were taken at each rainfall site, inoculated with a buffer of Botrytis cinerea mycelia, and then incubated for 4 days at 20° C. in a light atmosphere saturated with moisture. The specimens were then examined for erosion due to disease.

Under these conditions, the following was observed: a. With 5 mm of rainfall, the comparison was completely contaminated; b. With 5 mm of rain, the sample treated with iprodione as a wet powder was contaminated to the extent of 56%. In contrast, the sample treated with iprodione prepared according to the present invention was only 36% eroded; c At 10 mm of rainfall, the sample treated with iprodione as a textured powder was eroded to the extent of 87%. In contrast, the sample treated with iprodione formulated according to the present invention had only 31% erosion.

These examples clearly demonstrate that by using the compositions of the present invention, significant and surprising improvements in the effectiveness of iprodione were obtained.

Claims (1)

Claims: 1 by weight, a 20 to 40 iprodione-based active substances
% and b "oil-in-water" containing 50-160% by weight relative to iprodione of oil having a hydrophilic/lipophilic balance (HLB) of 8-12 on the HLB value scale for the preparation of "oil-in-water" emulsions. c) 0.1 to 2% of an ethylene oxide/aliphatic alcohol condensate type nonionic emulsifier, and (d) 0.5 to 2% of nearly neutral hydrophilic silica, if necessary.
An agricultural fungicidal composition based on iprodione containing 2.5% and . 2. Composition according to claim 1, characterized in that the oil has a hydrophilic/lipophilic balance of a value between 10 and 11. 3. The composition according to claim 1 or 2, characterized in that the oil can dissolve 1 to 5 g of iprodione per oil. 4. The composition according to any one of claims 1 to 3, wherein the oil is mineral oil. 5. The composition according to any one of claims 1 to 3, wherein the oil is a vegetable oil. 6. Claims 1 to 6, characterized in that the nonionic emulsifier is a condensate of one or more aliphatic alcohols having 12 to 14 carbon atoms and 8 to 12 moles of ethylene oxide. The composition according to any of paragraph 5. 7. The composition according to claim 6, wherein the emulsifier is a condensate of a synthetic alcohol having 13 carbon atoms and 9 to 10 moles of ethylene oxide. 8. The composition according to any one of claims 1 to 7, characterized in that the silica is a hydrated precipitated silica having a BET specific surface area of 200 to 300 m ² /g. 9. Composition according to any of claims 1 to 7, characterized in that the active substance is a mixture of iprodione and carbendazim.