Indian Patents. 224184:"FUNGICIDAL COMPOSITIONS COMPRISING CARPROPAMID, FLUODIOXONIL AND IMIDACLOPRID"

Title of Invention	"FUNGICIDAL COMPOSITIONS COMPRISING CARPROPAMID, FLUODIOXONIL AND IMIDACLOPRID"
Abstract	Fungicidal compositions, characterized by a content of an active compound combination comprising A) N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-methyl-cyclo-propanecarboxamide of the formula and B) 4-(2,2-difluoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile of the formula and C) l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine of the formula

Full Text	The present invention relates to fungicidal compositions comprising carpropamid, fluodioxonil and imidacloprid. The present invention relates to novel active compound combinations which are highly suitable for controlling phytopathogenic fungi and which comprise the known N-[ 1 -(4-chloro-phenyl)-ethyl]-2,2-dichloro-1 -ethyl-3-methyl-cyclopropane-carboxamide and two other known compounds which are fungicidally and in-secticidally active, respectively. It is already known that N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-meth-yl-cyclopropanecarboxamide and 4-(2,2-difiuoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile have fungicidal properties (cf. EP-A 0 341 475 and EP-A 0 206 999), and that l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine has insecticidal properties (cf. Pesticide Manual, 9th ed. (1991), page 491). It is also known that mixtures of N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-methyl-cyclopropanecarboxamide and 1 -[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine can be used for controlling fungi (cf. JP-A 271 207-1991). The activity both of the individual components and of the mixtures is good. However, the fungicidal potency at very low application rates is not always satis¬factory. It has now been found that the novel active compound combinations comprising A) N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-methyl-cyclopropane-carboxamide of the formula (Formula Removed) and B) 4-(2,2-difluoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile of the formula and C) l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine of the formula (Figure Removed) have very good fungicidal properties. Surprisingly, the fungicidal activity of the three-compound combinations according to the invention is significantly higher than the activities of the individual components or the activities of the prior art mixtures comprising two active compounds. There is therefore an unforeseeable synergistic effect, and not just a supplementary action. As is evident from the structural formula of the active compound of the formula (I), the compound has three asymmetrically substituted carbon atoms. The product may therefore be present as a mixture of different isomers, or else in the form of a single component. Particular preference is given to the compounds N-(R)-[l-(4-chloro-phenyl)-ethyl]-(lS)-2,2-dichloro-l-ethyl-t-3-methyl-r-l-cyclo-propanecarboxamide of the formula (Figure Removed) and N-(R)-[l-(4-chloro-phenyl)-ethyl]-(lR)-2,2-dichloro-l-ethyl-t-3-methyl-r-l-cyclo-propanecarboxamide of the formula (Figure Removed) The compound of the formula (I) and the individual isomers thereof are known (cf. EP-A 0 341 475). The active compound of the formula (II) is 4-(2,2-difluoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile known as a fungicide under the name fludioxonil (cf. EP-A 0 206 999). The active compound of the formula (III) is l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine known as an insecticide under the name imidacloprid (cf Pesticide Manual, 9th ed. (1991, page 491). The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within relatively broad ranges. In general, there are 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of the formula (II) and 0.1 to 1.5 parts by weight, preferably 0.1 to 1.0 parts by weight, of active compound of the formula (III) per part by weight of active compound of the formula (I). The active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes, etc. The active compound combinations according to the invention are particularly suitable for controlling Pyricularia, Pellicularia, Cochliobolus, Gibberella, Rhizoctonia and Fusarium spp. The active compound combinations according to the invention are particularly useful for controlling fungi in rice and cereals such as wheat and barley. The fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aerial parts of plants, of propagation stock and seeds, and of the soil. The active compound combinations according to the invention can be used for foliar application, or else as seed dressings. The active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations. These formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are mainly suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorilionite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, poly-oxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl-sulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose. Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils. It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally comprise between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%. The active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting. In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a relatively wide range. In general, they are between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%. In the treatment of seeds, amounts of 0.001 to 50 g of active compound per kilogram of seeds are generally required, preferably 0.01 to 10 g. In the treatment of the soil, active compound concentrations of 0.00001 to 0.1% by weight, preferably of 0.0001 to 0.02% by weight, are required at the site of action. The good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds and even the combinations of just two active compounds exhibit weaknesses with regard to the fungicidal activity, the three-compound combination has an activity which exceeds a simple addition of activities and also exceeds the activity of the known synergistic combinations. A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually. Example t Rhizoctonia solani test (cotton) / seed treatment The active compounds or the active compound combinations are applied as a seed treatment powder. This is prepared by extending the respective active compound with ground mineral to give a finely pulverulent mixture which guarantees uniform distribution on the seed surface. To dress the seed, the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask. The seed is sown at 2 x 50 channels at a depth of 2 cm in a potting compost which is infected with Rhizoctonia solani and grown in the greenhouse at a temperature of approximately 22°C in seed trays which receive a light regimen of 15 hours per day. 8 days after sowing, the plants are evaluated for symptoms. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. Active compounds, active compound concentrations and test results are stated in the table below. Table 1 Rhizoctonia solani test (cotton) / seed treatment (Table Removed) The mixture comprises identical amounts of (la) and (Ib). We Claim: 1.Fungicidal compositions, characterized by a content of an active compound combination comprising A) N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-methyl-cyclo-propanecarboxamide of the formula (Formula Removed) and B) 4-(2,2-difluoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile of the formula (Formula Removed) and C) l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine of the formula (Formula Removed) wherein the weight ratio of active compound of the formula (I) to active compound of the formula (II) and active compound of the formula (III) is between 1:0.1 and 1:10 and between 1:0.1 and 1:1.5, respectively. 2. Fungicidal compositions substantially as hereinbefore described with reference to the forgoing examples.

Full Text

The present invention relates to fungicidal compositions comprising carpropamid, fluodioxonil and imidacloprid.
The present invention relates to novel active compound combinations which are highly suitable for controlling phytopathogenic fungi and which comprise the known N-[ 1 -(4-chloro-phenyl)-ethyl]-2,2-dichloro-1 -ethyl-3-methyl-cyclopropane-carboxamide and two other known compounds which are fungicidally and in-secticidally active, respectively.
It is already known that N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-meth-yl-cyclopropanecarboxamide and 4-(2,2-difiuoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile have fungicidal properties (cf. EP-A 0 341 475 and EP-A 0 206 999), and that l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine has insecticidal properties (cf. Pesticide Manual, 9th ed. (1991), page 491).
It is also known that mixtures of N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-methyl-cyclopropanecarboxamide and 1 -[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine can be used for controlling fungi (cf. JP-A 271 207-1991). The activity both of the individual components and of the mixtures is good. However, the fungicidal potency at very low application rates is not always satis¬factory.
It has now been found that the novel active compound combinations comprising
A) N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-methyl-cyclopropane-carboxamide of the formula
(Formula Removed)
and
B) 4-(2,2-difluoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile of the formula
and
C) l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine of the formula

(Figure Removed)

have very good fungicidal properties.
Surprisingly, the fungicidal activity of the three-compound combinations according to the invention is significantly higher than the activities of the individual components or the activities of the prior art mixtures comprising two active compounds. There is therefore an unforeseeable synergistic effect, and not just a supplementary action.
As is evident from the structural formula of the active compound of the formula (I), the compound has three asymmetrically substituted carbon atoms. The product may therefore be present as a mixture of different isomers, or else in the form of a single component. Particular preference is given to the compounds
N-(R)-[l-(4-chloro-phenyl)-ethyl]-(lS)-2,2-dichloro-l-ethyl-t-3-methyl-r-l-cyclo-propanecarboxamide of the formula
(Figure Removed)
and
N-(R)-[l-(4-chloro-phenyl)-ethyl]-(lR)-2,2-dichloro-l-ethyl-t-3-methyl-r-l-cyclo-propanecarboxamide of the formula

(Figure Removed)
The compound of the formula (I) and the individual isomers thereof are known (cf. EP-A 0 341 475).
The active compound of the formula (II) is 4-(2,2-difluoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile known as a fungicide under the name fludioxonil (cf. EP-A 0 206 999).
The active compound of the formula (III) is l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine known as an insecticide under the name imidacloprid (cf Pesticide Manual, 9th ed. (1991, page 491).
The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within relatively broad ranges. In general, there are 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of the formula (II) and 0.1 to 1.5 parts by weight, preferably 0.1 to 1.0 parts by weight, of active compound of the formula (III) per part by weight of active compound of the formula (I).
The active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes, etc.
The active compound combinations according to the invention are particularly suitable for controlling Pyricularia, Pellicularia, Cochliobolus, Gibberella, Rhizoctonia and Fusarium spp.
The active compound combinations according to the invention are particularly useful for controlling fungi in rice and cereals such as wheat and barley.
The fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aerial parts of plants, of propagation stock and seeds, and of the soil. The active compound combinations according to the invention can be used for foliar application, or else as seed dressings.
The active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
These formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are mainly suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorilionite or diatomaceous earth, and ground synthetic minerals such as
finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, poly-oxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl-sulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.
The active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting.
In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a relatively wide range. In general, they are between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
In the treatment of seeds, amounts of 0.001 to 50 g of active compound per kilogram of seeds are generally required, preferably 0.01 to 10 g.
In the treatment of the soil, active compound concentrations of 0.00001 to 0.1% by weight, preferably of 0.0001 to 0.02% by weight, are required at the site of action.
The good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds and even the combinations of just two active compounds exhibit weaknesses with regard to the fungicidal activity, the three-compound combination has an activity which exceeds a simple addition of activities and also exceeds the activity of the known synergistic combinations.
A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
Example t
Rhizoctonia solani test (cotton) / seed treatment
The active compounds or the active compound combinations are applied as a seed treatment powder. This is prepared by extending the respective active compound with ground mineral to give a finely pulverulent mixture which guarantees uniform distribution on the seed surface.
To dress the seed, the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.
The seed is sown at 2 x 50 channels at a depth of 2 cm in a potting compost which is infected with Rhizoctonia solani and grown in the greenhouse at a temperature of approximately 22°C in seed trays which receive a light regimen of 15 hours per day.
8 days after sowing, the plants are evaluated for symptoms. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.
Active compounds, active compound concentrations and test results are stated in the table below.

Table 1
Rhizoctonia solani test (cotton) / seed treatment (Table Removed)
The mixture comprises identical amounts of (la) and (Ib).

We Claim:
1.Fungicidal compositions, characterized by a content of an active compound combination comprising
A) N-[l-(4-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl-3-methyl-cyclo-propanecarboxamide of the formula

(Formula Removed)
and
B) 4-(2,2-difluoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile of the formula

(Formula Removed)
and
C) l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine of the formula
(Formula Removed)

wherein the weight ratio of active compound of the formula (I) to active compound of the formula (II) and active compound of the formula (III) is between 1:0.1 and 1:10 and between 1:0.1 and 1:1.5, respectively.
2. Fungicidal compositions substantially as hereinbefore described with reference to the forgoing examples.

Documents:

3324-DEL-1997-Abstract-(08-09-2008).pdf

3324-DEL-1997-Abstract-(16-09-2008).pdf

3324-del-1997-abstract.pdf

3324-del-1997-assignment.pdf

3324-DEL-1997-Claims-(08-09-2008).pdf

3324-del-1997-claims.pdf

3324-DEL-1997-Correspondence-Others-(08-09-2008).pdf

3324-DEL-1997-Correspondence-Others-(10-09-2008).pdf

3324-del-1997-correspondence-others.pdf

3324-DEL-1997-Description (Complete)-(16-09-2008).pdf

3324-del-1997-description (complete)-08-09-2008.pdf

3324-del-1997-description (complete).pdf

3324-DEL-1997-Form-1-(08-09-2008).pdf

3324-DEL-1997-Form-1-(16-09-2008).pdf

3324-del-1997-form-1.pdf

3324-del-1997-form-13-(10-09-2008).pdf

3324-del-1997-form-18.pdf

3324-DEL-1997-Form-2-(08-09-2008).pdf

3324-DEL-1997-Form-2-(16-09-2008).pdf

3324-del-1997-form-2.pdf

3324-DEL-1997-Form-3-(08-09-2008).pdf

3324-del-1997-form-4.pdf

3324-del-1997-form-6.pdf

3324-DEL-1997-GPA-(08-09-2008).pdf

3324-del-1997-gpa.pdf

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Patent Number

224184

Indian Patent Application Number

3324/DEL/1997

PG Journal Number

44/2008

Publication Date

31-Oct-2008

Grant Date

01-Oct-2008

Date of Filing

20-Nov-1997

Name of Patentee

BAYER AKTIENGESELLSCHAFT

Applicant Address

D-51368 LEVERKUSEN, GERMANY.

Inventors:

#	Inventor's Name	Inventor's Address
1	GERD HANBLER	AM ARENZBERG 58A, 51381 LEVERKUSEN, GERMANY.
2	STEFAN DUTZMANN	WEIBENSTEIN 95, 40764 LANGENFELD, GERMANY.
3	YOSHI KURAHASHI	KAMIYAMA 1CHOME 4-14, OYAMA-SHI, TOCHIGI, JAPAN.

PCT International Classification Number

A01N 43/40

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA