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WO1998047370A1 - Fungicide active substance combinations - Google Patents

Fungicide active substance combinations Download PDF

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Publication number
WO1998047370A1
WO1998047370A1 PCT/EP1998/001987 EP9801987W WO9847370A1 WO 1998047370 A1 WO1998047370 A1 WO 1998047370A1 EP 9801987 W EP9801987 W EP 9801987W WO 9847370 A1 WO9847370 A1 WO 9847370A1
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WO
WIPO (PCT)
Prior art keywords
formula
active ingredient
group
derivative
compound
Prior art date
Application number
PCT/EP1998/001987
Other languages
German (de)
French (fr)
Inventor
Klaus Stenzel
Stefan Dutzmann
Astrid Mauler-Machnik
Lutz Assmann
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP98922648A priority Critical patent/EP0975221A1/en
Priority to AU75221/98A priority patent/AU727180B2/en
Priority to CA002286849A priority patent/CA2286849A1/en
Priority to KR1019997009142A priority patent/KR20010006064A/en
Priority to BR9809763-6A priority patent/BR9809763A/en
Priority to NZ500368A priority patent/NZ500368A/en
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to PL98336225A priority patent/PL336225A1/en
Priority to IL13190198A priority patent/IL131901A0/en
Priority to JP54492398A priority patent/JP2001505924A/en
Priority to US09/402,908 priority patent/US6297236B1/en
Publication of WO1998047370A1 publication Critical patent/WO1998047370A1/en
Priority to BG103789A priority patent/BG103789A/en

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to new combinations of active ingredients which consist of known halogen-benzimidazoles on the one hand and other known fungicidal active ingredients on the other hand and which are very suitable for combating phytopathogenic fungi.
  • X represents chlorine or phenyl
  • R 1 represents hydrogen or methyl
  • Me Zn or Mn or mixture of Zn and Mn
  • R 2 represents methyl or cyclopropyl
  • n stands for integers from 0 to 5 and
  • R 3 represents hydrogen (17 to 23%) or the rest of the formula
  • the fungicidal action of the active compound combinations according to the invention is considerably higher than the sum of the actions of the individual active compounds. So there is an unforeseeable, real synergistic effect and not just an addition.
  • Formula (I) includes
  • halogen benzimidazoles of the formulas (Ia) and (Ib) are known (cf. WO 97-
  • Formula (II) includes the compounds
  • Formula (IV) comprises the aniline derivatives of the formulas
  • the compound has three asymmetrically substituted carbon atoms.
  • the product can therefore be a mixture of different isomers or in the form of a single one
  • the compounds are particularly preferred N- (R) - [1 - (4-chlorophenyl) ethyl] - (1 S) -2,2-dichloro-1-ethyl-3t-methyl-1 r-cyclopropanecarboxamide of the formula
  • Formula (VII) includes the compounds
  • Formula (XVI) includes the compounds
  • the guanidine derivative of the formula (XXV) is a mixture of substances with the common name guazatine.
  • the active ingredient combinations according to the invention contain at least one active ingredient from the compounds of groups (1) to (25). They can also contain other fungicidal admixing components.
  • the active compounds are present in the active compound combinations according to the invention in certain weight ratios, the synergistic effect is particularly evident.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within a relatively wide range. In general, 1 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 used to control phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
  • the active compound combinations according to the invention are particularly suitable for combating cereal diseases, such as Erysiphe, Puccinia and Fusarium, and for combating diseases in viticulture, such as Uncinula, Plasmopara and Botrytis, and also in dicotyledon crops for combating real and
  • the active compound combinations according to the invention can be used for foliar application or as a mordant.
  • the active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders,
  • formulations are prepared in a known manner, for example by mixing the active ingredients or combinations of active ingredients with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes 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
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants such as butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates.
  • granules e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Possible emulsifying and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ether,
  • Alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyanin blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyanin blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and also in mixtures with fertilizers or
  • the active compound combinations can be used as such, in the form of their formulations or 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 usual way, e.g. by pouring, spraying, spraying, scattering, spreading, dry pickling, wet pickling, wet pickling, slurry pickling or incrusting.
  • the application rates can be varied within a substantial range, depending on the type of application.
  • the application rates of active compound combination are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the amount of active ingredient combination used is generally between 0.001 and 50 g per kilo grams of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of active compound combination are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the good fungicidal activity of the active compound combinations according to the invention can be seen from the examples below. While the individual active ingredients have weaknesses in their fungicidal action, the combinations show an action that goes beyond a simple summation of action.
  • Fungicides always have a synergistic effect if the fungicidal activity of the active ingredient combinations is greater than the sum of the effects of the individually applied active ingredients.
  • X means the efficiency when using the active ingredient A in an application rate of m g / ha
  • Y means the efficiency when using the active ingredient B in an application rate of n g / ha and
  • E means the efficiency when using active ingredients A and B in application rates of m and n g / ha
  • the efficiency is determined in%. It means 0% an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the combination of the combination is superadditive, i.e. there is a synergistic effect.
  • the actually observed efficiency must be greater than the value for the expected efficiency (E) calculated from the above formula.
  • Emulsifier 3 parts by weight of alkylaryl polyglycol ether
  • active compound or combination of active compounds 1 part by weight of active compound or combination of active compounds is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or combination of active compounds is diluted with water to the desired concentration.
  • Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the active ingredients are used as dry mordants. They are prepared by stripping the respective active ingredient or the combination of active impacts with stone powder to form a fine powder mixture which ensures an even distribution on the seed surface.
  • the infected seed is shaken with the dressing in a sealed glass bottle for 3 minutes.
  • the triticale is sown with 2 x 100 seeds 1 cm deep in a standard soil and cultivated in a greenhouse at a temperature of approx. 10 ° C and a relative humidity of approx. 95% in seed boxes that are exposed to light for 15 hours a day.
  • 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • the active ingredients are used as dry mordants. They are prepared by stripping the respective active ingredient or combination of active ingredients with rock flour to form a fine powder mixture which ensures an even distribution on the seed surface.
  • the infected seed is shaken with the dressing in a sealed glass bottle for 3 minutes.
  • the seeds are sown with 2 x 50 seeds 2 cm deep in a Pythium sp. naturally infected compost and cultivate it in the greenhouse at a temperature of around 20 ° C in seed boxes that are exposed to the light for 15 hours a day.
  • the evaluation is carried out after 14 days. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The new active substance combinations of an halogen benzimidazol of formula (I), in which Z stands for chlorine or bromine, and of the groups of active substances (1 to 25) listed in the description have very good fungicide properties.

Description

Fungizide WirkstoffkombinationenFungicidal active ingredient combinations
Die vorliegende Erfindung betrifft neue Wirkstoffkombinationen, die aus bekannten Halogen-benzimidazolen einerseits und weiteren bekannten fungiziden Wirkstoffen andererseits bestehen und sehr gut zur Bekämpfung von phytopathogenen Pilzen geeignet sind.The present invention relates to new combinations of active ingredients which consist of known halogen-benzimidazoles on the one hand and other known fungicidal active ingredients on the other hand and which are very suitable for combating phytopathogenic fungi.
Es ist bereits bekannt, daß l-(3,5-Dimethyl-isoxazol-4-sulfonyl)-2-brom-6,6-difluor- [l,3]-dioxolo-[4,5fj-benzimidazol und l-(3,5-Dimethyl-isoxazol-4-sulfonyl)-2-chlor- 6,6-di£luor-[l,3]-dioxolo-[4,5f]-benzimidazol fungizide Eigenschaften besitzen (vgl.It is already known that 1- (3,5-dimethyl-isoxazole-4-sulfonyl) -2-bromo-6,6-difluoro- [1,3] -dioxolo- [4,5fj-benzimidazole and 1- ( 3,5-dimethyl-isoxazole-4-sulfonyl) -2-chloro-6,6-di £ luor- [1,3] -dioxolo- [4,5f] -benzimidazole possess fungicidal properties (cf.
WO 97-06171). Die Wirksamkeit dieser Stoffe ist gut, läßt aber bei niedrigen Aufwandmengen in manchen Fällen zu wünschen übrig.WO 97-06171). The effectiveness of these substances is good, but leaves something to be desired in some cases at low application rates.
Ferner ist schon bekannt, daß zahlreiche Triazol-Derivate, Anilin-Derivate, Dicarb- oximide und andere Heterocyclen zur Bekämpfung von Pilzen eingesetzt werden können (vgl. EP-A 0 040 345, DE-A 22 01 063, DE-A 23 24 010, Pesticide Manual, 9th. Edition (1991), Seiten 249 und 827, EP-A 0 382 375 und EP-A 0 515 901). Auch die Wirkung dieser Stoffe ist aber bei niedrigen Aufwandmengen nicht immer ausreichend.Furthermore, it is already known that numerous triazole derivatives, aniline derivatives, dicarboximides and other heterocycles can be used to combat fungi (cf. EP-A 0 040 345, DE-A 22 01 063, DE-A 23 24 010, Pesticide Manual, 9th Edition (1991), pages 249 and 827, EP-A 0 382 375 and EP-A 0 515 901). However, the effect of these substances is not always sufficient at low application rates.
Schließlich ist auch bekannt, daß l-[(6-Chlor-3-pyridinyl)-methyl]-N-nitro-2-imidazo- lidinimin zur Bekämpfung tierischer Schädlinge, wie Insekten, verwendbar ist (vgl. Pesticide Manual, 9th. Edition (1991), Seite 491). Fungizide Eigenschaften dieses Stoffes wurden aber bisher noch nicht beschrieben.Finally, it is also known that l - [(6-chloro-3-pyridinyl) methyl] -N-nitro-2-imidazolidinimine can be used to control animal pests, such as insects (cf. Pesticide Manual, 9th edition (1991), page 491). Fungicidal properties of this substance have not yet been described.
Es wurde nun gefunden, daß die neuen WirkstofEkombinationen aus einem Halogen- benzimidazol der Formel
Figure imgf000004_0001
It has now been found that the new active compound combinations consist of a halogenobenzimidazole of the formula
Figure imgf000004_0001
in welcherin which
für Chlor oder Brom steht,represents chlorine or bromine,
undand
(1) einem Triazol-Derivat der Formel(1) a triazole derivative of the formula
Figure imgf000004_0002
Figure imgf000004_0002
in welcherin which
X für Chlor oder Phenyl steht, undX represents chlorine or phenyl, and
— C— — CH-- C— - CH-
II III I
Y für ° oder 0H steht,Y stands for ° or 0H ,
und/oderand or
(2) dem Triazol-Derivat der Formel nazol)
Figure imgf000005_0001
(2) the triazole derivative of the formula nazole)
Figure imgf000005_0001
und/oderand or
(3) einem Anilin-Derivat der Formel(3) an aniline derivative of the formula
Figure imgf000005_0002
Figure imgf000005_0002
in welcherin which
R1 für Wasserstoff oder Methyl steht,R 1 represents hydrogen or methyl,
und/oderand or
(4) N-[ 1 -(4-Chlor-ρhenyl)-ethyl]-2,2-dichlor- 1 -ethyl-3 -methyl-cyclopropan-car- bonsäureamid der Formel(4) N- [1 - (4-chloro-ρhenyl) ethyl] -2,2-dichloro-1-ethyl-3-methylcyclopropane-carboxamide of the formula
Figure imgf000005_0003
Figure imgf000005_0003
und/oderand or
(5) dem Zink-propylen- 1 ,2-bis-(dithiocarbamidat) der Formel CH, S(5) the zinc propylene 1,2-bis (dithiocarbamidate) of the formula CH, S
I II I
— [Zn— S— C— NH— CH2 — CH— NH— C-S] —- [Zn— S— C— NH— CH 2 - CH— NH— CS] -
(VI) n > = (Propineb)(VI) n> = (Propineb)
und/oderand or
(6) mindestens einem Thiocarbamat der Formel(6) at least one thiocarbamate of the formula
Figure imgf000006_0001
Figure imgf000006_0001
Me = Zn oder Mn oder Gemisch aus Zn und MnMe = Zn or Mn or mixture of Zn and Mn
und/oderand or
(7) dem Anilin-Derivat der Formel(7) the aniline derivative of the formula
Figure imgf000006_0002
Figure imgf000006_0002
(Fenhexamid)(Fenhexamide)
und/oderand or
(8) der Verbindung der Formel(8) the compound of formula
Figure imgf000006_0003
und/oder
Figure imgf000006_0003
and or
(9) dem Benzothiadiazol-Derivat der Formel(9) the benzothiadiazole derivative of the formula
Figure imgf000007_0001
Figure imgf000007_0001
und/oderand or
(10) dem 8-t-Butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-l,4-dioxaspiro[5,4]- decan der Formel(10) the 8-t-butyl-2- (N-ethyl-N-n-propylamino) methyl-1,4-dioxaspiro [5,4] decane of the formula
Figure imgf000007_0002
Figure imgf000007_0002
(Spiroxamin)(Spiroxamine)
und/oderand or
(11) der Verbindung der Formel(11) the compound of formula
Figure imgf000007_0003
Figure imgf000007_0003
und/oder (12) der Verbindung der Formeland or (12) the compound of formula
Figure imgf000008_0001
Figure imgf000008_0001
und/oderand or
(13) der Verbindung der Formel(13) the compound of formula
Figure imgf000008_0002
Figure imgf000008_0002
und/oderand or
(14) dem Cyanoxim-Derivat der Formel(14) the cyanoxime derivative of the formula
O O CNO O CN
II II III II I
CH— CH— H— C-NH-C-C=NOCH3 (XV)CH— CH— H— C-NH-CC = STILL 3 (XV)
(Cymoxanil)(Cymoxanil)
und/oderand or
(15) einem Pyrimidin-Derivat der Formel
Figure imgf000009_0001
(15) a pyrimidine derivative of the formula
Figure imgf000009_0001
in welcherin which
R2 für Methyl oder Cyclopropyl steht,R 2 represents methyl or cyclopropyl,
und/oderand or
(16) dem Anilin-Derivat der Formel(16) the aniline derivative of the formula
Figure imgf000009_0002
Figure imgf000009_0002
und/oderand or
(17) dem Morpholin-Derivat der Formel(17) the morpholine derivative of the formula
(XVIII)(XVIII)
Figure imgf000009_0003
Figure imgf000009_0003
und/oder (18) dem Phthalimid-Derivat der Formeland or (18) the phthalimide derivative of the formula
Figure imgf000010_0001
Figure imgf000010_0001
und/oderand or
(19) der Phosphor- Verbindung der Formel(19) the phosphorus compound of the formula
Figure imgf000010_0002
Figure imgf000010_0002
und/oderand or
(20) dem Hydroxyethyl-triazol-Derivat der Formel(20) the hydroxyethyl triazole derivative of the formula
Figure imgf000010_0003
Figure imgf000010_0003
und/oderand or
(21 ) dem 1 -[(6-Chlor-3 -pyridinyl)-methyl]-N-nitro-2-imidazolidinimin der Formel
Figure imgf000011_0001
(21) the 1 - [(6-chloro-3-pyridinyl) methyl] -N-nitro-2-imidazolidinimine of the formula
Figure imgf000011_0001
und/oderand or
(22) dem Oxazolidindion der Formel(22) the oxazolidinedione of the formula
(XXIII)(XXIII)
(Famoxadone)
Figure imgf000011_0002
und/oder
(Famoxadone)
Figure imgf000011_0002
and or
(23) dem Benzamid-Derivat der Formel(23) the benzamide derivative of the formula
Figure imgf000011_0003
Figure imgf000011_0003
und/oderand or
(24) einem Guanidin-Derivat der Formel(24) a guanidine derivative of the formula
3 R3 3 R 3
R3— N— (CH2)8-[N— (CH2)8]-N-H (XXV) π x (2 + m) CH3COOHR 3 - N - (CH 2 ) 8 - [N - (CH 2 ) 8 ] -NH (XXV) π x (2 + m) CH 3 COOH
in welcher m für ganze Zahlen von 0 bis 5 steht undin which m stands for integers from 0 to 5 and
R3 für Wasserstoff (17 bis 23 %) oder den Rest der FormelR 3 represents hydrogen (17 to 23%) or the rest of the formula
-C=NH | (77 bis 83 %)-C = NH | (77 to 83%)
NH.NH.
steht.stands.
und/oderand or
(25) dem Triazol-Derivat der Formel(25) the triazole derivative of the formula
Figure imgf000012_0001
Figure imgf000012_0001
sehr gute fungizide Eigenschaften besitzen.have very good fungicidal properties.
Überraschenderweise ist die fungizide Wirkung der erfindungsgemäßen Wirk- stofl-kombinationen wesentlich höher als die Summe der Wirkungen der einzelnen Wirkstoffe. Es liegt also ein nicht vorhersehbarer, echter synergistischer Effekt vor und nicht nur eine Wirkungsergänzung.Surprisingly, the fungicidal action of the active compound combinations according to the invention is considerably higher than the sum of the actions of the individual active compounds. So there is an unforeseeable, real synergistic effect and not just an addition.
Die Formel (I) umfaßtFormula (I) includes
das l-(3,5-Dimethyl-isoxazol-4-sulfonyl)-2-brom-6,6-difluor-[l,3]-dioxok)- [4,5fj-benzimidazol der Formel
Figure imgf000013_0001
the l- (3,5-dimethyl-isoxazole-4-sulfonyl) -2-bromo-6,6-difluoro- [1,3] -dioxok) - [4,5fj-benzimidazole of the formula
Figure imgf000013_0001
undand
das l-(3,5-Dimethyl-isoxazol-4-sulfonyl)-2-chlor-6,6-difluor-[l,3]-dioxolo- [4,5f]-benzimidazol der Formelthe l- (3,5-dimethyl-isoxazole-4-sulfonyl) -2-chloro-6,6-difluoro- [1,3] -dioxolo- [4,5f] -benzimidazole of the formula
Figure imgf000013_0002
Figure imgf000013_0002
Die Halogen-benzimidazole der Formeln (la) und (Ib) sind bekannt (vgl. WO 97-The halogen benzimidazoles of the formulas (Ia) and (Ib) are known (cf. WO 97-
06171).06171).
Die Formel (II) umfaßt die VerbindungenFormula (II) includes the compounds
l-(4-Chlor-phenoxy)-3,3-dimethyl-l-(l,2,4-triazol-l-yl)-butan-2-on der Formel1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-l-yl) -butan-2-one of the formula
Figure imgf000013_0003
Figure imgf000013_0003
1 -(4-Chlor-phenoxy)-3 ,3 -dimethyl- 1 -( 1 ,2,4-triazol- 1 -yl)-butan-2-ol der Formel
Figure imgf000014_0001
1 - (4-chlorophenoxy) -3, 3 -dimethyl-1 - (1, 2,4-triazol-1-yl) -butan-2-ol of the formula
Figure imgf000014_0001
undand
1 -(4-Phenyl-phenoxy)-3 , 3 -dimethyl- 1 -( 1 , 2,4-triazol- 1 -yl)-butan-2-ol der Formel1 - (4-phenyl-phenoxy) -3, 3-dimethyl-1 - (1, 2,4-triazol-1-yl) -butan-2-ol of the formula
Figure imgf000014_0002
Figure imgf000014_0002
Die Formel (IV) umfaßt die Anilin-Derivate der FormelnFormula (IV) comprises the aniline derivatives of the formulas
Figure imgf000014_0003
Figure imgf000014_0003
undand
Figure imgf000014_0004
Figure imgf000014_0004
Aus der Strukturformel für den Wirkstoff der Formel (V) ist ersichtlich, daß die Verbindung drei asymmetrisch substituierte Kohlenstofifatome aufweist. Das Produkt kann daher als Gemisch von verschiedenen Isomeren oder auch in Form einer einzigenIt can be seen from the structural formula for the active ingredient of the formula (V) that the compound has three asymmetrically substituted carbon atoms. The product can therefore be a mixture of different isomers or in the form of a single one
Komponente vorliegen. Besonders bevorzugt sind die Verbindungen N-(R)-[ 1 -(4-Chlor-phenyl)-ethyl]-( 1 S)-2,2-dichlor- 1 -ethyl-3t-methyl- 1 r-cyclopropan- carbonsäureamid der FormelComponent. The compounds are particularly preferred N- (R) - [1 - (4-chlorophenyl) ethyl] - (1 S) -2,2-dichloro-1-ethyl-3t-methyl-1 r-cyclopropanecarboxamide of the formula
Figure imgf000015_0001
Figure imgf000015_0001
(S) (R)(S) (R)
undand
N-(R)-[l-(4-Chlor-phenyl)-ethyl]-(lR)-2,2-dichlor-l-ethyl-3t-methyl-lr-cycloρropan- carbonsäureamid der FormelN- (R) - [1- (4-chlorophenyl) ethyl] - (IR) -2,2-dichloro-l-ethyl-3t-methyl-lr-cyclopropanecarboxamide of the formula
Figure imgf000015_0002
Figure imgf000015_0002
Die Formel (VII) umfaßt die VerbindungenFormula (VII) includes the compounds
(Vlla) Me = Zn (Zineb),(Vlla) Me = Zn (Zineb),
(Vllb) Me = Mn (Maneb) und(Vllb) Me = Mn (Maneb) and
(VIIc) Mischung aus (Vlla) und (Vllb) (Mancozeb).(VIIc) mixture of (Vlla) and (Vllb) (Mancozeb).
Die Formel (XVI) umfaßt die VerbindungenFormula (XVI) includes the compounds
(XVIa) R2 = CH3 (Pyrimethanil) und(XVIa) R 2 = CH 3 (pyrimethanil) and
(XVIb) R2 = (Cyprodinyl) Das Hydroxyethyl-triazol-Derivat der Formel (XXI) kann in der „Thiono"-Form der Formel(XVIb) R2 = (Cyprodinyl) The hydroxyethyl-triazole derivative of the formula (XXI) can be in the "thiono" form of the formula
Figure imgf000016_0001
Figure imgf000016_0001
oder in der tautomeren „Mercapto"-Form der Formelor in the tautomeric "mercapto" form of the formula
Figure imgf000016_0002
Figure imgf000016_0002
vorliegen. Der Einfachheit halber wird jeweils nur die „Thiono"-Form aufgeführt.available. For the sake of simplicity, only the "Thiono" shape is listed.
Bei dem Guanidin-Derivat der Formel (XXV) handelt es sich um ein Substanzgemisch mit dem Common Name Guazatine.The guanidine derivative of the formula (XXV) is a mixture of substances with the common name guazatine.
Die in den erfindungsgemäßen WirkstofEkombinationen neben einem Halogen-benz- imidazol der Formel (I) vorhandenen Komponenten sind ebenfalls bekannt. Im einzelnen werden die Wirkstoffe in den folgenden Publikationen beschrieben:The components present in the active compound combinations according to the invention in addition to a halogenobenzimidazole of the formula (I) are also known. The active substances are described in detail in the following publications:
(1) Verbindungen der Formel (II)(1) compounds of the formula (II)
DE-A 22 01 063 DE-A 23 24 010 (2) Verbindung der Formel (III) EP-A 0 040 345DE-A 22 01 063 DE-A 23 24 010 (2) Compound of formula (III) EP-A 0 040 345
(3) Verbindungen der Formel (IV)(3) compounds of the formula (IV)
Pesticide Manual, 9th. Ed. (1991), Seiten 249 und 827Pesticide Manual, 9th. Ed. (1991), pages 249 and 827
(4) Verbindung der Formel (V) und deren einzelne Derivate(4) Compound of formula (V) and its individual derivatives
EP-A 0 341 475EP-A 0 341 475
(5) Verbindung der Formel (VI)(5) Compound of Formula (VI)
Pesticide Manual, 9th. Ed. (1991), Seite 726Pesticide Manual, 9th. Ed. (1991), page 726
(6) Verbindungen der Formel (VII) Pesticide Manual, 9th. Ed. (1991), Seiten 529, 531 und 866(6) Compounds of Formula (VII) Pesticide Manual, 9th. Ed. (1991), pages 529, 531 and 866
(7) Verbindung der Formel (VIII)(7) Compound of Formula (VIII)
EP-A 0 339 418EP-A 0 339 418
(8) Verbindung der Formel (IX)(8) Compound of Formula (IX)
EP-A 0 472 996EP-A 0 472 996
(9) Verbindung der Formel (X)(9) compound of formula (X)
EP-A 0 313 512EP-A 0 313 512
( 10) Verbindung der Formel (XI)(10) compound of formula (XI)
EP-A 0 281 842EP-A 0 281 842
(11) Verbindung der Formel (XII) EP-A 0 382 375(11) Compound of formula (XII) EP-A 0 382 375
(12) Verbindung der Formel (XIII) EP-A 0 515 901(12) compound of formula (XIII) EP-A 0 515 901
(13) Verbindung der Formel (XIV)(13) compound of formula (XIV)
DE-A 196 02 095DE-A 196 02 095
( 14) Verbindung der Formel (XV)(14) compound of formula (XV)
Pesticide Manual, 9th. Ed. (1991), Seite 206Pesticide Manual, 9th. Ed. (1991), page 206
(15) Verbindungen der Formel (XVI) EP-A 0 270 111(15) Compounds of the formula (XVI) EP-A 0 270 111
EP-A 0 310 550EP-A 0 310 550
( 16) Verbindung der Formel (XVΗ)(16) compound of the formula (XVΗ)
Pesticide Manual, 9th. Ed. (1991), Seite 554Pesticide Manual, 9th. Ed. (1991), page 554
(17) Verbindung der Formel (XN )(17) compound of formula (XN)
EP-A 0 219 756EP-A 0 219 756
(18) Verbindung der Formel (XIX) Pesticide Manual, 9th. Ed. (1991), Seite 431(18) Compound of Formula (XIX) Pesticide Manual, 9th. Ed. (1991), page 431
(19) Verbindung der Formel (XX)(19) compound of the formula (XX)
Pesticide Manual, 9th. Ed. (1991), Seite 443Pesticide Manual, 9th. Ed. (1991), page 443
(20) Verbindung der Formel (XXI)(20) compound of the formula (XXI)
WO 96-16048WO 96-16048
(21 ) Verbindung der Formel (XXII)(21) Compound of Formula (XXII)
Pesticide Manual, 9th. Ed. (1991), Seite 491Pesticide Manual, 9th. Ed. (1991), page 491
(22) Verbindung der Formel (XXm) EP-A 0 393 911 (23) Verbindung der Formel (XXIV)(22) Compound of the formula (XXm) EP-A 0 393 911 (23) compound of the formula (XXIV)
EP-A 0 600 629EP-A 0 600 629
(24) Substanz der Formel (XXV)(24) Substance of the formula (XXV)
Pesticide Manual, 9th. Ed. (1991), Seite 461Pesticide Manual, 9th. Ed. (1991), page 461
(25) Verbindung der Formel (XXVI)(25) compound of the formula (XXVI)
Pesticide Manual, 9th. Ed. (1991), Seite 654Pesticide Manual, 9th. Ed. (1991), page 654
Die erfindungsgemäßen WirkstofEkombinationen enthalten neben einem Wirkstoff der Formel (I) mindestens einen Wirkstoff von den Verbindungen der Gruppen (1) bis (25). Sie können darüberhinaus auch weitere füngizid wirksame Zumischkomponen- ten enthalten.In addition to an active ingredient of the formula (I), the active ingredient combinations according to the invention contain at least one active ingredient from the compounds of groups (1) to (25). They can also contain other fungicidal admixing components.
Wenn die Wirkstoffe in den erfindungsgemäßen Wirkstoffkombinationen in bestimmten Gewichtsverhältnissen vorhanden sind, zeigt sich der synergistische Effekt besonders deutlich. Jedoch können die Gewichtsverhältnisse der Wirkstoffe in den Wirkstoffkombinationen in einem relativ großen Bereich variiert werden. Im allgemeinen entfallen auf 1 Gewichtsteil an Wirkstoff der Formel (I)If the active compounds are present in the active compound combinations according to the invention in certain weight ratios, the synergistic effect is particularly evident. However, the weight ratios of the active ingredients in the active ingredient combinations can be varied within a relatively wide range. In general, 1 part by weight of active compound of the formula (I)
0,1 bis 20 Gewichtsteile, vorzugsweise 0,2 bis 10 Gewichtsteile an Wirkstoff aus der Gruppe (1),0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight of active ingredient from group (1),
0, 1 bis 20 Gewichtsteile, vorzugsweise 0,2 bis 10 Gewichtsteile an Wirkstoff aus der Gruppe (2),0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, of active ingredient from group (2),
1 bis 150 Gewichtsteile, vorzugsweise 1 bis 100 Gewichtsteile an Wirkstoff aus der Gruppe (3), 0, 1 bis 10 Gewichtsteile, vorzugsweise 0,2 bis 5 Gewichtsteile an Wirkstoff aus der Gruppe (4),1 to 150 parts by weight, preferably 1 to 100 parts by weight, of active ingredient from group (3), 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active ingredient from group (4),
1 bis 150 Gewichtsteile, vorzugweise 5 bis 100 Gewichtsteile an Wirkstoff aus der Gruppe (5),1 to 150 parts by weight, preferably 5 to 100 parts by weight of active ingredient from group (5),
1 bis 150 Gewichtsteile, vorzugsweise 5 bis 100 Gewichtsteile an Wirkstoff aus der Gruppe (6),1 to 150 parts by weight, preferably 5 to 100 parts by weight, of active ingredient from group (6),
0,1 bis 50 Gewichtsteile, vorzugsweise 1 bis 20 Gewichtsteile an Wirkstoff aus der0.1 to 50 parts by weight, preferably 1 to 20 parts by weight of active ingredient from the
Gruppe (7),Group (7),
0, 1 bis 50 Gewichtsteile, vorzugsweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (8)0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active ingredient from group (8)
0,02 bis 50 Gewichtsteile, vorzugsweise 0, 1 bis 10 Gewichtsteile an Wirkstoff aus der Gruppe (9),0.02 to 50 parts by weight, preferably 0.1 to 10 parts by weight of active ingredient from group (9),
0,1 bis 20 Gewichtsteile, vorzugsweise 0,5 bis 10 Gewichtsteile an Wirkstoff aus der Gruppe (10),0.1 to 20 parts by weight, preferably 0.5 to 10 parts by weight of active ingredient from group (10),
0,1 bis 50 Gewichtsteile, vorzugsweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (11),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active ingredient from group (11),
0, 1 bis 50 Gewichtsteile, vorzugsweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (12),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active ingredient from group (12),
0, 1 bis 50 Gewichtsteile, vorzugweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (13), 0, 1 bis 50 Gewichtsteile, vorzugsweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (14),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active ingredient from group (13), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active ingredient from group (14),
0,2 bis 50 Gewichtsteile, vorzugsweise 1 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (15),0.2 to 50 parts by weight, preferably 1 to 20 parts by weight, of active ingredient from group (15),
0, 1 bis 50 Gewichtsteile, vorzugsweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (16),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active ingredient from group (16),
0,1 bis 50 Gewichtsteile, vorzugsweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (17),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active ingredient from group (17),
1 bis 150 Gewichtsteile, vorzugweise 5 bis 100 Gewichtsteile an Wirkstoff aus der Gruppe (18),1 to 150 parts by weight, preferably 5 to 100 parts by weight of active ingredient from the group (18),
0, 1 bis 150 Gewichtsteile, vorzugsweise 1 bis 100 Gewichtsteile an Wirkstoff aus der Gruppe (19),0.1 to 150 parts by weight, preferably 1 to 100 parts by weight, of active ingredient from group (19),
0,02 bis 50 Gewichtsteile, vorzugsweise 0,2 bis 10 Gewichtsteile an Wirkstoff aus der Gruppe (20),0.02 to 50 parts by weight, preferably 0.2 to 10 parts by weight, of active ingredient from group (20),
0,05 bis 20 Gewichtsteile, vorzugsweise 0, 1 bis 10 Gewichtsteile an Wirkstoff aus der Gruppe (21),0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight of active ingredient from group (21),
0, 1 bis 50 Gewichtsteile, vorzugsweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (22),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active ingredient from group (22),
0, 1 bis 50 Gewichtsteile, vorzugweise 0,2 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (23), 0,02 bis 50 Gewichtsteile, vorzugsweise 0,04 bis 10 Gewichtsteile an Wirkstoff aus der Gruppe (24) und/oder0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active ingredient from group (23), 0.02 to 50 parts by weight, preferably 0.04 to 10 parts by weight of active ingredient from group (24) and / or
0,2 bis 50 Gewichtsteile, vorzugsweise 1 bis 20 Gewichtsteile an Wirkstoff aus der Gruppe (25).0.2 to 50 parts by weight, preferably 1 to 20 parts by weight of active ingredient from group (25).
Die erfindungsgemäßen Wirkstoffkombinationen besitzen sehr gute fungizide Eigenschaften und lassen sich zur Bekämpfung von phytopathogenen Pilzen, wie Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomy- cetes, Basidiomycetes, Deuteromycetes usw. einsetzen.The active compound combinations according to the invention have very good fungicidal properties and can be used to control phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
Die erfindungsgemäßen Wirkstoffkombinationen eignen sich besonders gut zur Bekämpfung von Getreidekrankheiten, wie Erysiphe, Puccinia und Fusarium, sowie zur Bekämpfung von Krankheiten im Weinbau, wie Uncinula, Plasmopara und Botrytis, und außerdem in dikotylen Kulturen zur Bekämpfung von Echten undThe active compound combinations according to the invention are particularly suitable for combating cereal diseases, such as Erysiphe, Puccinia and Fusarium, and for combating diseases in viticulture, such as Uncinula, Plasmopara and Botrytis, and also in dicotyledon crops for combating real and
Falschen Mehltaupilzen sowie Blattfleckenerregern.Downy mildew fungi and leaf stain pathogens.
Die gute Pflanzenverträglichkeit der Wirkstoffkombinationen in den zur Bekämpfung von Pflanzenkrankheiten notwendigen Konzentrationen erlaubt eine Behand- lung von oberirdischen Pflanzenteilen, von Pflanz- und Saatgut, und des Bodens.The fact that the active ingredient combinations are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
Die erfindungsgemäßen Wirkstoffkombinationen können zur Blattapplikation oder auch als Beizmittel eingesetzt werden.The active compound combinations according to the invention can be used for foliar application or as a mordant.
Die erfindungsgemäßen Wirkstoffkombinationen können in die üblichen Formulie- rungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver,The active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders,
Schäume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-Formulierungen.Foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermi- sehen der Wirkstoffe bzw. der Wirkstoffkombinationen mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktio- nen, Alkohole, wie Butanol oder Glycol sowie deren Ether und Ester, Ketone, wieThese formulations are prepared in a known manner, for example by mixing the active ingredients or combinations of active ingredients with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes 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
Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser. Mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase, wie Butan, Propan, Stickstoff und Kohlendioxid. Als feste Trägerstoffe kommen in Frage: z.B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate. Als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengel. Als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fett- säureester, Polyoxyethylen-Fettalkoholether, z.B. Alkylarylpolyglycol-ether,Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates. The following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems. Possible emulsifying and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ether,
Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate. Als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.Alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natür- liehe und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Fer- rocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalo- cyaninfarbstoffe und Spurennährstoffe, wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyanin blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
Die Formulierungen enthalten im allgemeinen zwischen 0, 1 und 95 Gew.-% Wirkstoffe, vorzugsweise zwischen 0,5 und 90 % .The formulations generally contain between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.
Die erfmdungsgemäßen Wirkstoffkombinationen können in den Formulierungen in Mischung mit anderen bekannten Wirkstoffen vorliegen, wie Fungiziden, Insektizi- den, Akariziden und Herbiziden, sowie in Mischungen mit Düngemitteln oderThe active compound combinations according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and also in mixtures with fertilizers or
Pflanzenwachstumsregulatoren.Plant growth regulators.
Die Wirkstoffkombinationen können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, emulgierbare Konzentrate, Emulsionen, Suspensionen, Spritzpulver, lösliche Pulver und Granulate, angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Verspritzen, Versprühen, Verstreuen, Verstreichen, Trockenbeizen, Feuchtbeizen, Naßbeizen, Schlämmbeizen oder Inkrustieren.The active compound combinations can be used as such, in the form of their formulations or 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 usual way, e.g. by pouring, spraying, spraying, scattering, spreading, dry pickling, wet pickling, wet pickling, slurry pickling or incrusting.
Beim Einsatz der erfindungsgemäßen Wirkstoffkombinationen können die Aufwandmengen je nach Applikationsart innerhalb eines größeren Bereichs variiert werden. Bei der Behandlung von Pflanzenteilen liegen die Aufwandmengen an Wirkstoffkombination im allgemeinen zwischen 0, 1 und 10 000 g/ha, vorzugsweise zwischen 10 und 1 000 g/ha. Bei der Saatgutbehandlung liegen die Aufwandmen- gen an Wirkstoffkombination im allgemeinen zwischen 0,001 und 50 g pro Kilo- gramm Saatgut, vorzugsweise zwischen 0,01 und 10 g pro Kilogramm Saatgut. Bei der Behandlung des Bodens liegen die Aufwandmengen an Wirkstoffkombination im allgemeinen zwischen 0,1 und 10 000 g/ha, vorzugsweise zwischen 1 und 5 000 g/ha.When using the active compound combinations according to the invention, the application rates can be varied within a substantial range, depending on the type of application. In the treatment of parts of plants, the application rates of active compound combination are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the amount of active ingredient combination used is generally between 0.001 and 50 g per kilo grams of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active compound combination are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
Die gute fungizide Wirkung der erfindungsgemäßen Wirkstoffkombinationen geht aus den nachfolgenden Beispielen hervor. Während die einzelnen Wirkstoffe in der fungiziden Wirkung Schwächen aufweisen, zeigen die Kombinationen eine Wirkung, die über eine einfache Wirkungssummierung hinausgeht.The good fungicidal activity of the active compound combinations according to the invention can be seen from the examples below. While the individual active ingredients have weaknesses in their fungicidal action, the combinations show an action that goes beyond a simple summation of action.
Ein synergistischer Effekt liegt bei Fungiziden immer dann vor, wenn die fungizide Wirkung der Wirkstoffkombinationen größer ist als die Summe der Wirkungen der einzeln applizierten Wirkstoffe.Fungicides always have a synergistic effect if the fungicidal activity of the active ingredient combinations is greater than the sum of the effects of the individually applied active ingredients.
Die zu erwartende Wirkung für eine gegebene Kombination zweier Wirkstoffe kann nach S.R. Colby („Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds J_5 (1967), 20-22) wie folgt berechnet werden:The expected effect for a given combination of two active ingredients can, according to S.R. Colby ("Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds J_5 (1967), 20-22) can be calculated as follows:
WennIf
X den Wirkungsgrad beim Einsatz des Wirkstoffes A in einer Aufwandmenge von m g/ha bedeutet,X means the efficiency when using the active ingredient A in an application rate of m g / ha,
Y den Wirkungsgrad beim Einsatz des Wirkstoffes B in einer Aufwandmenge von n g/ha bedeutet undY means the efficiency when using the active ingredient B in an application rate of n g / ha and
E den Wirkungsgrad beim Einsatz der Wirkstoffe A und B in Aufwandmengen von m und n g/ha bedeutet,E means the efficiency when using active ingredients A and B in application rates of m and n g / ha,
dann ist X - Ythen X - Y
E = X + Y -E = X + Y -
100100
Dabei wird der Wirkungsgrad in % ermittelt. Es bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, daß kein Befall beobachtet wird.The efficiency is determined in%. It means 0% an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Ist die tatsächliche fungizide Wirkung größer als berechnet, so ist die Kombination in ihrer Wirkung überadditiv, d.h. es liegt ein synergistischer Effekt vor. In diesem Fall muß der tatsächlich beobachtete Wirkungsgrad größer sein als der aus der oben ange- führten Formel errechnete Wert für den erwarteten Wirkungsgrad (E).If the actual fungicidal activity is greater than calculated, the combination of the combination is superadditive, i.e. there is a synergistic effect. In this case, the actually observed efficiency must be greater than the value for the expected efficiency (E) calculated from the above formula.
Die Erfindung wird durch die folgenden Beispiele veranschaulicht. The invention is illustrated by the following examples.
Beispiel 1example 1
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Lösungsmittel: 47 Gewichtsteile AcetonSolvent: 47 parts by weight of acetone
Emulgator: 3 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 3 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt 1 Gewichtsteil Wirkstoff oder Wirkstoffkombination mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration oder man verdünnt eine handelsübliche Formulierung von Wirkstoff oder Wirkstoffkombination mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound or combination of active compounds is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or combination of active compounds is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit werden junge Pflanzen mit der WirkstoflEzu- bereitung in der angegebenen Aufwandmenge besprüht. Nach Antrocknen des Spritzbelages werden die Pflanzen mit einer wäßrigen Sporensuspension von Phytophthora infestans inokuliert. Die Pflanzen werden dann in einer Inkubationskabine bei ca. 20°C und 100 % relativer Luftfeuchtigkeit aufgestellt.To test for protective efficacy, young plants are sprayed with the preparation of active compound in the application rate given. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at approx. 20 ° C and 100% relative humidity.
3 Tage nach der Inokulation erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, daß kein Befall beobachtet wird.Evaluation is carried out 3 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Wirkstoffe, Aufwandmengen und Versuchsergebnisse gehen aus der folgenden Tabelle hervor. Tabelle 1Active substances, application rates and test results are shown in the following table. Table 1
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000028_0001
Tabelle 1 (Fortsetzung)
Figure imgf000028_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000029_0001
Tabelle 1 (Fortsetzung)
Figure imgf000029_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000030_0001
Tabelle 1 (Fortsetzung)
Figure imgf000030_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000031_0001
Tabelle 1 (Fortsetzung)
Figure imgf000031_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000032_0001
Tabelle 1 (Fortsetzung)
Figure imgf000032_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000033_0001
Tabelle 1 (Fortsetzung)
Figure imgf000033_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000034_0001
Tabelle 1 (Fortsetzung)
Figure imgf000034_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000035_0001
Tabelle 1 (Fortsetzung)
Figure imgf000035_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000036_0001
Tabelle 1 (Fortsetzung)
Figure imgf000036_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000037_0001
Tabelle 1 (Fortsetzung)
Figure imgf000037_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000038_0001
Tabelle 1 (Fortsetzung)
Figure imgf000038_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000039_0001
Tabelle 1 (Fortsetzung)
Figure imgf000039_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000040_0001
Tabelle 1 (Fortsetzung)
Figure imgf000040_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000041_0001
Tabelle 1 (Fortsetzung)
Figure imgf000041_0001
Table 1 (continued)
Phytophthora-Test (Tomate) / protektivPhytophthora test (tomato) / protective
Figure imgf000042_0001
ber. = nach der Colby-Formel berechneter Wirkungsgrad
Figure imgf000042_0001
calc. = efficiency calculated according to the Colby formula
Beispiel 2Example 2
Fusarium nivale-Test (Triticale) / SaatgutbehandlungFusarium nivale test (triticale) / seed treatment
Die Anwendung der Wirkstoffe erfolgt als Trockenbeizmittel. Sie werden zubereitet durch Abstrecken des jeweiügen Wirkstoffes oder der Wirkstoßkombination mit Gesteinsmehl zu einer feinpulvrigen Mischung, die eine gleichmäßige Verteilung auf der Saatgutoberfläche gewährleistet.The active ingredients are used as dry mordants. They are prepared by stripping the respective active ingredient or the combination of active impacts with stone powder to form a fine powder mixture which ensures an even distribution on the seed surface.
Zur Beizung schüttelt man das infizierte Saatgut 3 Minuten lang mit dem Beizmittel in einer verschlossenen Glasflasche.For the dressing, the infected seed is shaken with the dressing in a sealed glass bottle for 3 minutes.
Den Triticale sät man mit 2 x 100 Korn 1 cm tief in eine Standarderde und kultiviert ihn im Gewächshaus bei einer Temperatur von ca. 10°C und einer relativen Luftfeuchtigkeit von ca. 95 % in Saatkästen, die täglich 15 Stunden dem Licht ausgesetzt werden.The triticale is sown with 2 x 100 seeds 1 cm deep in a standard soil and cultivated in a greenhouse at a temperature of approx. 10 ° C and a relative humidity of approx. 95% in seed boxes that are exposed to light for 15 hours a day.
Ca. 3 Wochen nach der Aussaat erfolgt die Auswertung der Pflanzen auf Symptome. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, daß kein Befall beobachtet wird.Approximately The plants are evaluated for symptoms 3 weeks after sowing. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Wirkstoffe, Aufwandmengen und Versuchsergebnisse gehen aus der folgenden Tabelle hervor. Active substances, application rates and test results are shown in the following table.
Tabelle 2Table 2
Fusarium nivale-Test (Triticale) / SaatgutbehandlungFusarium nivale test (triticale) / seed treatment
Figure imgf000044_0001
Figure imgf000044_0001
Beispiel 3Example 3
Pythium sp.-Test (Erbse) / SaatgutbehandlungPythium sp. Test (pea) / seed treatment
Die Anwendung der Wirkstoffe erfolgt als Trockenbeizmittel. Sie werden zubereitet durch Abstrecken des jeweiligen Wirkstoffes oder der Wirkstofßombination mit Gesteinsmehl zu einer feinpulvrigen Mischung, die eine gleichmäßige Verteilung auf der Saatgutoberfläche gewährleistet.The active ingredients are used as dry mordants. They are prepared by stripping the respective active ingredient or combination of active ingredients with rock flour to form a fine powder mixture which ensures an even distribution on the seed surface.
Zur Beizung schüttelt man das infizierte Saatgut 3 Minuten lang mit dem Beizmittel in einer verschlossenen Glasflasche.For the dressing, the infected seed is shaken with the dressing in a sealed glass bottle for 3 minutes.
Das Saatgut sät man mit 2 x 50 Korn 2 cm tief in eine mit Pythium sp. natürlich infizierte Komposterde und kultiviert es im Gewächshaus bei einer Temperatur von ca. 20°C in Saatkästen, die täglich 15 Stunden dem Licht ausgesetzt werden.The seeds are sown with 2 x 50 seeds 2 cm deep in a Pythium sp. naturally infected compost and cultivate it in the greenhouse at a temperature of around 20 ° C in seed boxes that are exposed to the light for 15 hours a day.
Nach 14 Tagen erfolgt die Auswertung. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, daß kein Befall beobachtet wird.The evaluation is carried out after 14 days. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Wirkstoffe, Aufwandmengen und Versuchsergebnisse gehen aus der folgenden Tabelle hervor. Active substances, application rates and test results are shown in the following table.
Tabelle 3Table 3
Pythium sp.-Test (Erbse) / SaatgutbehandlungPythium sp. Test (pea) / seed treatment
Figure imgf000046_0001
Figure imgf000046_0001

Claims

Patentansprüche claims
1. Fungizide Mittel, gekennzeichnet durch einen Gehalt an einer Wirkstoffkombination, bestehend aus1. Fungicidal compositions, characterized by a content of an active ingredient combination consisting of
einem Halogen-benzimidazol der Formela halogen benzimidazole of the formula
Figure imgf000047_0001
Figure imgf000047_0001
in welcherin which
Z für Chlor oder Brom steht,Z represents chlorine or bromine,
undand
(1) einem Triazol-Derivat der Formel(1) a triazole derivative of the formula
Figure imgf000047_0002
Figure imgf000047_0002
in welcherin which
X für Chlor oder Phenyl steht, und — C— — CH-X represents chlorine or phenyl, and - C— - CH-
II III I
Y für ° oder OH steht,Y stands for ° or OH ,
und/oderand or
(2) dem Triazol-Derivat der Formel(2) the triazole derivative of the formula
nazol)
Figure imgf000048_0001
nazole)
Figure imgf000048_0001
und/oderand or
(3) einem Anilin-Derivat der Formel(3) an aniline derivative of the formula
Figure imgf000048_0002
Figure imgf000048_0002
in welcherin which
R1 für Wasserstoff oder Methyl steht,R 1 represents hydrogen or methyl,
und/oderand or
(4) N-[ 1 -(4-Chlor-phenyl)-ethyl]-2,2-dichlor- 1 -ethyl-3-methyl-cyclo- propan-carbonsäureamid der Formel
Figure imgf000049_0001
(4) N- [1 - (4-chlorophenyl) ethyl] -2,2-dichloro-1-ethyl-3-methyl-cyclopropane-carboxamide of the formula
Figure imgf000049_0001
und/oderand or
(5) dem Zink-propylen- 1 ,2-bis-(dithiocarbamidat) der Formel(5) the zinc propylene 1,2-bis (dithiocarbamidate) of the formula
-[Zn— S— C— NH— CH2 — CH — NH — C-S]—- [Zn— S— C— NH— CH 2 - CH - NH - CS] -
(VI) n > = 1 (Propineb)(VI) n> = 1 (propineb)
und/oderand or
(6) mindestens einem Thiocarbamat der Formel(6) at least one thiocarbamate of the formula
Figure imgf000049_0002
Figure imgf000049_0002
Me = Zn oder Mn oder Gemisch aus Zn und MnMe = Zn or Mn or mixture of Zn and Mn
und/oderand or
(7) dem Anilin-Derivat der Formel
Figure imgf000050_0001
(7) the aniline derivative of the formula
Figure imgf000050_0001
(Fenhexamid)(Fenhexamide)
und/oderand or
(8) der Verbindung der Formel(8) the compound of formula
Figure imgf000050_0002
Figure imgf000050_0002
und/oderand or
(9) dem Benzothiadiazol-Derivat der Formel(9) the benzothiadiazole derivative of the formula
Figure imgf000050_0003
Figure imgf000050_0003
und/oderand or
(10) dem 8-t-Butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-l,4-dioxaspiro- [5,4]-decan der Formel(10) the 8-t-butyl-2- (N-ethyl-N-n-propylamino) methyl-1,4-dioxaspiro [5,4] decane of the formula
Figure imgf000050_0004
(Spiroxamin) und/oder
Figure imgf000050_0004
(Spiroxamine) and or
(11) der Verbindung der Formel(11) the compound of formula
Figure imgf000051_0001
Figure imgf000051_0001
und/oderand or
(12) der Verbindung der Formel(12) the compound of formula
Figure imgf000051_0002
Figure imgf000051_0002
und/oderand or
(13) der Verbindung der Formel(13) the compound of formula
Figure imgf000051_0003
Figure imgf000051_0003
und/oder ( 14) dem Cyanoxim-Derivat der Formeland or (14) the cyanoxime derivative of the formula
0 o CN0 o CN
II II III II I
CH— CH— NH— C-NH-C-C=NOCH3 (XV)CH— CH— NH— C-NH-CC = STILL 3 (XV)
(Cymoxanil)(Cymoxanil)
und/oderand or
(15) einem Pyrimidin-Derivat der Formel(15) a pyrimidine derivative of the formula
Figure imgf000052_0001
Figure imgf000052_0001
in welcherin which
R2 für Methyl oder Cyclopropyl steht,R 2 represents methyl or cyclopropyl,
und/oderand or
(16) dem Anilin-Derivat der Formel(16) the aniline derivative of the formula
Figure imgf000052_0002
Figure imgf000052_0002
und/oder (17) dem Morpholin-Derivat der Formeland or (17) the morpholine derivative of the formula
(XVIII)(XVIII)
Figure imgf000053_0001
Figure imgf000053_0001
und/oderand or
(18) dem Phthalimid-Derivat der Formel(18) the phthalimide derivative of the formula
Figure imgf000053_0002
Figure imgf000053_0002
und/oderand or
( 19) der Phosphor- Verbindung der Formel(19) the phosphorus compound of the formula
Figure imgf000053_0003
Figure imgf000053_0003
und/oderand or
(20) dem Hydroxyethyl-triazol-Derivat der Formel
Figure imgf000054_0001
(20) the hydroxyethyl triazole derivative of the formula
Figure imgf000054_0001
und/oderand or
(21) dem l-[(6-CWor-3-pyridinyl)-methyl]-N-mtro-2-irddazolidinimin der Formel(21) the l - [(6-CWor-3-pyridinyl) methyl] -N-mtro-2-irddazolidinimine of the formula
Cl N N-N°2 (Imidacloprid) Cl NN - N ° 2 (imidacloprid)
und/oderand or
(22) dem Oxazolidindion der Formel(22) the oxazolidinedione of the formula
(XXIII)(XXIII)
(Famoxadone)
Figure imgf000054_0002
(Famoxadone)
Figure imgf000054_0002
und/oderand or
(23) dem Benzamid-Derivat der Formel
Figure imgf000055_0001
(23) the benzamide derivative of the formula
Figure imgf000055_0001
und/oderand or
(24) einem Guanidin-Derivat der Formel(24) a guanidine derivative of the formula
3 R3 3 R 3
R— N— (CH2)8-[N— (CH2)Θ]-N-H (XXV) π x (2 + m) CH3COOH in welcherR— N— (CH 2 ) 8 - [N— (CH 2 ) Θ ] -NH (XXV) π x (2 + m) CH 3 COOH in which
m für ganze Zahlen von 0 bis 5 steht undm stands for integers from 0 to 5 and
R3 für Wasserstoff ( 17 bis 23 %) oder den Rest der FormelR 3 represents hydrogen (17 to 23%) or the rest of the formula
-C=NH | (77 bis 83 %)-C = NH | (77 to 83%)
NH,NH,
steht,stands,
und/oderand or
(25) dem Triazol-Derivat der Formel
Figure imgf000056_0001
(25) the triazole derivative of the formula
Figure imgf000056_0001
2. Mittel gemäß Anspruch 1, dadurch gekennzeichnet, daß in den Wirkstoflf- kombinationen das Gewichtsverhältnis von Wirkstoff der Formel (I) zu2. Composition according to claim 1, characterized in that in the active ingredient combinations, the weight ratio of active ingredient of formula (I)
Wirkstoff der Gruppe (1) zwischen 1:0,1 und 1:20 liegt, Wirkstoff der Gruppe (2) zwischen 1 :0,1 und 1:20 liegt, Wirkstoff der Gruppe (3) zwischen 1 : 1 und 1: 150 liegt, Wirkstoff der Gruppe (4) zwischen 1:0,1 und 1:10 liegt, Wirkstoff der Gruppe (5) zwischen 1 : 1 und 1:150 liegt, Wirkstoff der Gruppe (6) zwischen 1 : 1 und 1:150 liegt, Wirkstoff der Gruppe (7) zwischen 1:0,1 und 1 :50 liegt, Wirkstoff der Gruppe (8) zwischen 1:0,1 und 1:50 liegt, Wirkstoff der Gruppe (9) zwischen 1:0,02 und 1:50 liegt, Wirkstoff der Gruppe (10) zwischen 1:0,1 und 1:20 liegt,Active ingredient of group (1) is between 1: 0.1 and 1:20, active ingredient of group (2) is between 1: 0.1 and 1:20, active ingredient of group (3) is between 1: 1 and 1: 150 is, active ingredient of group (4) is between 1: 0.1 and 1:10, active ingredient of group (5) is between 1: 1 and 1: 150, active ingredient of group (6) is between 1: 1 and 1: 150 is, active ingredient of group (7) is between 1: 0.1 and 1:50, active ingredient of group (8) is between 1: 0.1 and 1:50, active ingredient of group (9) is between 1: 0.02 and 1:50, active ingredient of group (10) is between 1: 0.1 and 1:20,
■ Wirkstoff der Gruppe (11) zwischen 1:0,1 und 1:50 liegt, • Wirkstoff der Gruppe (12) zwischen 1:0,1 und 1:50 liegt,■ active ingredient of group (11) is between 1: 0.1 and 1:50, • active ingredient of group (12) is between 1: 0.1 and 1:50,
■ Wirkstoff der Gruppe (13) zwischen 1:0,1 und 1 :50 liegt,Active ingredient of group (13) is between 1: 0.1 and 1:50,
■ Wirkstoff der Gruppe (14) zwischen 1:0,1 und 1:50 liegt,Active ingredient of group (14) is between 1: 0.1 and 1:50,
■ Wirkstoff der Gruppe (15) zwischen 1 :0,2 und 1 :50 liegt,Active ingredient of group (15) is between 1: 0.2 and 1:50,
■ Wirkstoff der Gruppe (16) zwischen 1 :0,1 und 1 :50 liegt,Active ingredient of group (16) is between 1: 0.1 and 1:50,
■ Wirkstoff der Gruppe (17) zwischen 1 :0,1 und 1 :50 liegt,Active ingredient of group (17) is between 1: 0.1 and 1:50,
■ Wirkstoff der Gruppe (18) zwischen 1 : 1 und 1: 150 liegt,Active ingredient of group (18) is between 1: 1 and 1: 150,
- Wirkstoff der Gruppe (19) zwischen 1:0,1 und 1 :150 liegt,Active ingredient of group (19) is between 1: 0.1 and 1: 150,
■ Wirkstoff der Gruppe (20) zwischen 1:0,02 und 1:50 liegt,Active ingredient of group (20) is between 1: 0.02 and 1:50,
- Wirkstoff der Gruppe (21) zwischen 1 :0,05 und 1:20 liegt,Active ingredient of group (21) is between 1: 0.05 and 1:20,
■ Wirkstoff der Gruppe (22) zwischen 1 :0,1 und 1 :50 liegt, - Wirkstoff der Gruppe (23) zwischen 1 :0,1 und 1:50 liegt,Active ingredient of group (22) is between 1: 0.1 and 1:50, Active ingredient of group (23) is between 1: 0.1 and 1:50,
- Wirkstoff der Gruppe (24) zwischen 1 :0,02 und 1 :50 liegt und- Active ingredient of group (24) is between 1: 0.02 and 1: 50 and
- Wirkstoff der Gruppe (25) zwischen 1:0,2 und 1:50 liegt.- Active ingredient of group (25) is between 1: 0.2 and 1:50.
3. Verfahren zur Bekämpfung von Pilzen, dadurch gekennzeichnet, daß man WirkstofEkombinationen gemäß Anspruch 1 auf die Pilze und/oder deren Lebensraum ausbringt.3. Process for combating fungi, characterized in that active ingredient combinations according to claim 1 are applied to the fungi and / or their habitat.
4. Verwendung von Wirkstofl-kombinationen gemäß Anspruch 1 zur Bekämpfung von Pilzen.4. Use of drug combinations according to claim 1 for combating fungi.
5. Verfahren zur Herstellung von fungiziden Mitteln, dadurch gekennzeichnet, daß man WirkstofEkombinationen gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt. 5. A process for the preparation of fungicidal agents, characterized in that active ingredient combinations according to claim 1 are mixed with extenders and / or surface-active substances.
PCT/EP1998/001987 1997-04-18 1998-04-06 Fungicide active substance combinations WO1998047370A1 (en)

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AU75221/98A AU727180B2 (en) 1997-04-18 1998-04-06 Fungicide active compound combinations
CA002286849A CA2286849A1 (en) 1997-04-18 1998-04-06 Fungicide active substance combinations
KR1019997009142A KR20010006064A (en) 1997-04-18 1998-04-06 Fungicide active substance combinations
BR9809763-6A BR9809763A (en) 1997-04-18 1998-04-06 Combinations of fungicidal active substances
NZ500368A NZ500368A (en) 1997-04-18 1998-04-06 Synergistic fungicidal combinations comprising a halogeno-benzimidazole and a triazole
EP98922648A EP0975221A1 (en) 1997-04-18 1998-04-06 Fungicide active substance combinations
PL98336225A PL336225A1 (en) 1997-04-18 1998-04-06 Combinations of a fungicidally active compound
IL13190198A IL131901A0 (en) 1997-04-18 1998-04-06 Fungicidal active compound combinations
JP54492398A JP2001505924A (en) 1997-04-18 1998-04-06 Combination of fungicidal and fungicide active substances
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AU2002233248B2 (en) * 2000-12-18 2006-12-21 Basf Aktiengesellschaft Carbamate-based fungicidal mixtures
WO2002049438A2 (en) * 2000-12-18 2002-06-27 Basf Aktiengesellschaft Carbamate-based fungicidal mixtures
WO2002054871A1 (en) * 2001-01-16 2002-07-18 Basf Aktiengesellschaft Fungicide mixtures
WO2002054870A2 (en) * 2001-01-16 2002-07-18 Basf Aktiengesellschaft Fungicide mixtures based on imidazole derivatives
WO2002054870A3 (en) * 2001-01-16 2002-12-12 Basf Ag Fungicide mixtures based on imidazole derivatives
WO2002056690A1 (en) * 2001-01-22 2002-07-25 Basf Aktiengesellschaft Fungicide mixtures
US7449195B2 (en) 2001-01-22 2008-11-11 Basf Aktiengesellschaft Fungicide mixtures
CN1310585C (en) * 2002-03-21 2007-04-18 巴斯福股份公司 Fungicidal mixtures
EP1790226A3 (en) * 2002-03-21 2007-09-05 Basf Aktiengesellschaft Fungicidal mixtures
EP1790226A2 (en) * 2002-03-21 2007-05-30 Basf Aktiengesellschaft Fungicidal mixtures
EA010093B1 (en) * 2002-03-21 2008-06-30 Басф Акциенгезельшафт Fungicidal mixtures
WO2003090538A1 (en) * 2002-03-21 2003-11-06 Basf Aktiengesellschaft Fungicidal mixtures
EP2080433A3 (en) * 2002-03-21 2009-12-09 Basf Se Fungicidal mixtures
AU2003218790B2 (en) * 2002-03-21 2010-03-25 Basf Se Fungicidal mixtures
AU2010202592B2 (en) * 2002-03-21 2013-01-31 Basf Se Fungicidal mixtures

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ID24677A (en) 2000-07-27
BG103789A (en) 2000-06-30
CN1252692A (en) 2000-05-10
JP2001505924A (en) 2001-05-08
TW385232B (en) 2000-03-21
DE19716256A1 (en) 1998-10-22
TR199902450T2 (en) 2000-01-21
PL336225A1 (en) 2000-06-19
CA2286849A1 (en) 1998-10-29
ZA983235B (en) 1998-10-22
AU7522198A (en) 1998-11-13
IL131901A0 (en) 2001-03-19
BR9809763A (en) 2000-06-20
EP0975221A1 (en) 2000-02-02
AU727180B2 (en) 2000-12-07
NZ500368A (en) 2000-09-29
CO5040019A1 (en) 2001-05-29
KR20010006064A (en) 2001-01-15
HUP0002361A3 (en) 2002-02-28
HUP0002361A2 (en) 2000-11-28

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