KR19980042660A - Fungicidal Active Combination - Google Patents

Abstract

The invention relates to 4- (2,2-difluoro-1,3-benzodioxol-7-yl)-of A) of formula (I) and B) of formula (II), which have very good fungicidal properties. Novel active formulation containing 1H-pyrrole-3-carbonitrile and C) 1-[(6-chloro-3-pyridinyl) -methyl] -N-nitro-2-imidazolidineimine of formula (III) It is about:

(Ⅰ)

(Ⅱ)

(Ⅲ)

Description

Fungicidal Active Combination

The present invention is well suited for controlling plant pathological fungi and relates to novel active formulations containing two known compounds, each known and each being fungicidally and pesticidally active.

And 4- (2,2-difluoro-1,3-benzodioxol-7-yl) -1H-pyrrole-3-carbonitrile have fungicidal properties (EP-A 0 341 475 and EP -A 0 206 999), it is already known that 1-[(6-chloro-3-pyridinyl) -methyl] -N-nitro-2-imidazolidineimine has pesticidal properties (Pesticide Manual, 9th edition (1991), p491).

It is also known that a mixture of 1-[(6-chloro-3-pyridinyl) -methyl] -N-nitro-2-imidazolidineimine can be used to control fungi (JP-A 271 2071991 Reference). The activity of the individual components and mixtures are all excellent. However, the fungicidal efficacy is not always satisfactory, at very low application rates.

According to the present invention a novel active formulation is formulated as 4- (2,2-difluoro-1,3-benzodioxol-7-yl) -1H of the following formula A) and B) New active formulations containing pyrrole-3-carbonitrile and C) 1-[(6-chloro-3-pyridinyl) -methyl] -N-nitro-2-imidazolidineimine of formula (III) It has been found to have very good fungicidal properties;

(Ⅰ)

(Ⅱ)

(Ⅲ)

Surprisingly, the fungicidal activity of the combination of the three compounds according to the invention is significantly superior to that of the individual constituents or of the prior art mixtures containing the two active compounds. Thus, this formulation has an unexpected synergistic effect and is not a complementary action.

As is apparent from the structural formula of the active compound of formula (I), the compound has three badly substituted carbon atoms. Thus, the product may be present as a mixture of different isomers or else in the form of a single construct. Particularly preferred compounds are those of the formula (Ia) and of the formula (Ib)

(Ia)

(Ib)

The compounds of formula (I) and their individual isomers are known (see EP-A 0 341 475).

The active compound of formula II is 4- (2,2-difluoro-1,3-benzodioxol-7-yl) -1H-pyrrole-3-carbo, known as a fungicide under the name fludioxonil. Nitrile (see EP-A 0 206 999).

The active compound of formula III is 1-[(6-chloro-3-pyridinyl) -methyl] -N-nitro-2-imidazolidineimine known as an insecticide under the name of imidaclopridra (Pesticide Manual, 9). Plate (1991), p491).

Synergistic effects occur especially when the active compounds in the active combinations according to the invention are present in a certain weight ratio. However, the weight ratio of active compound in the active formulation can be varied within a relatively wide range. Generally, the active compound of formula (II) is 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, and the active compound of formula (III) is 0.1 to 1.5 per 1 part by weight of the active compound of formula (I). Parts by weight, preferably 0.1 to 1.0 parts by weight.

The active compound according to the present invention has very good fungicidal properties, Plasmodiophoromycetes (Plasmodiophoromycetes), Ohmycetes (Oomycetes), Chitridiomycetes (Chytridiomycetes), Zygomycetes (Zygomycetes) ), Ascomycetes, Basidiomycetes and Deuteromycetes can be used to control phytopathological fungi.

The active formulations according to the invention are in particular Pyricularia, Peliicularia, Cochliobolus, Gibberella, Rhizoctonia and Fusarium spp. ) Is suitable for relief.

The active formulations according to the invention are particularly useful for controlling fungi in rice and cereals such as wheat and barley.

Active formulations that are resistant to plants at the concentrations necessary to control plant diseases are allowed to treat the public exposed portions of the plants and the stems and seeds, and the soil. The active formulations according to the invention can also be used for dressing leaves or else seed.

The active formulations according to the invention can be converted into conventional formulations such as solutions, emulsifiers, suspensions, powders, foams, pastes, granules, aerosols and compositions for coating microcapsules and seeds in polymers, and ULV formulations. .

These agents may be mixed in known manner, for example, with an extender, such as a liquid solvent, a gas liquefied under pressure, and / or a solid carrier, and optionally a surfactant, ie an emulsifier and / or a dispersant, and / or It is produced using a foam former together. In the case of using water as the extender, the organic solvent can also be used, for example, as an additional solvent. Mainly suitable as a liquid solvent below.

Aromatics such as xylene, toluene or alkylnaphthalenes, aromatic chlorides or aliphatic hydrocarbon chlorides such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins such as For example, petroleum fractions, alcohols such as butanol or glycols and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as Dimethylformamide and dimethylsulfoxide, or else water.

Liquefied gaseous extenders or carriers can be understood to mean liquids which are gaseous at ambient temperature and atmospheric pressure, for example sprays such as butane, propane, nitrogen and carbon dioxide.

Suitable solid carriers are as follows: solid carriers include, for example, kaolin, clay, talc, chalk, quartz, attapulgite, pulverized natural rock powder such as montmorillonite or diatomaceous earth, and highly dispersed silica, aluminum and silicates Synthetic rock powder is suitable. Solid carriers for granulation include, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husk, corncobs and tobacco stems. Granules of material are suitable. Emulsifiers and / or foaming agents include, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, aryl sulfo Nate and proteolytic products are suitable. Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose, gum arabic, polyvinyl alcohol, powders such as polyvinyl acetate, natural and synthetic polymers in the form of granules or emulsions, or else natural phospholipids such as cephalin and lecithin, and synthetic phospholipids Can be used for As other additives, mineral oil and vegetable oil may be used.

Traces such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and colorants such as azine dyes, azo dyes and organic dyes such as metal phthalocyanine dyes and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc You can also use nutrients.

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

The active formulations may be used in their own or in their preparation form, or in diluted forms such as ready-to-use solutions, emulsifying thickeners, emulsifiers, suspending agents, wetting powders, water soluble powders and granules. It is used by conventional methods such as watering for irrigation, spraying, spraying, spreading, spraying and dried seed treatment, water soluble powder for slurry treatment or shelling.

In plant treatment, the concentration of active compound in the form of use can be varied within a relatively wide range. Generally, 1 to 0.0001% by weight, preferably 0.5 to 0.001% by weight.

In the treatment of seeds, the active compound per kilogram of seed generally requires from 0.001 to 50 g, preferably from 0.01 to 10 g.

In the treatment of soils, the concentration of active compound required at the site of action is from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight.

Excellent fungicidal activity of the active formulations according to the invention was demonstrated in the following examples. Even the individual active compounds and the combination of the two active compounds show low fungicidal activity, while the combination of the three compounds has activity over the simple addition of the active and also over the activity of existing synergistic combinations. .

There is always a synergistic effect of fungicides when the fungicidal activity of the active formulations exceeds the combined activity of the active compounds when applied individually.

Example 1

Rhizoctonia solani (cotton) test / seed treatment The active compound or active compound is applied as a seed treatment powder. It was prepared by increasing each active compound with pulverized minerals to make the resulting mixture showing a uniform distribution on the seed surface.

To dress the seeds, the infected seeds along with the dressed seeds were shaken for 3 minutes in a sealed glass flask.

Seeds were sown in 2 × 50 grooves, 2 cm deep, with compost infected with lysoctonia solanii, and grown in seed containers receiving 15 hours of light per day in a greenhouse at a temperature of about 22 ° C.

After 8 days of sowing, the symptoms of the plants were observed. 0% represents the efficiency corresponding to the untreated control, while 100% efficiency means that no disease was observed.

Active compounds, active compound concentrations and test results are shown in the table below.

*) The mixture contains the same amount of (Ia) and (Ib).

Claims (5)

A) 4- (2,2-difluoro-1,3-benzodioxol-7-yl) -1H-pyrrole-3-carbonitrile and C of the following structural formula (I) A fungicidal composition comprising an active compound containing 1-[(6-chloro-3-pyridinyl) -methyl] -N-nitro-2-imidazolidineimine of formula (III) : (Ⅰ) (Ⅱ) (Ⅲ) The weight of the active compound of formula (I): the weight of the active compound of formula (II) is 1: 0.1 to 1:10, the weight of the active compound of formula (I): A composition characterized in that the active compound has a weight of the active compound of 1: 0.1 to 1: 1.5. A method for controlling fungi, characterized by acting on the fungi and / or their habitats according to claim 1. Use of the active formulation according to claim 1 for controlling fungi. A process for preparing a fungicidal composition, characterized in that the active compound according to claim 1 is mixed with an extender and / or a surfactant.