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(11) Patent Number: KE 458

(21)Application Number: KElP/ 2008/ 000756

(45)Dateofgrant: 09/08/2011

(22) Filing Date:27/11/2006
           
(51) Int.CI.8:A 01N 37/50, 43/54, A 01P 3/00               

(73) Owner: BAYER CROPSCIENCE AG of A1fred-Nobe1-Str. 50, 40789 Monheirn, Germany
       
(72) Inventors: WACHENDORFF-NEUMANN, Ulrike ofOberer Markenweg 85, 56566 Neuwie, Germany; DAHMEN, Peter of A1tebrticker Str. 61, 41470 Neuss, Germany; WITZENBERGER, Albert ofEschenallee 52, 51399 Burscheid, Germany and HAUSER-HAHN, Isolde of Diinfelder Str. 22, 51375 Leverkusen, Germany

(74) Agent/address for correspondence: Kaplan & Stratton Advocates,  P.O. Box 40111-00100, Nairobi

(30) Priority data:102005058838.7  09/12/2005  DE
           
(86)  PCT data PCT/EP06/011334    27/11/2006 wo 2007/065576    14/06/2007

(54) Title: FUNGICIDAL ACTIVE SUBSTANCE COMBINATION.

(57) Abstract: The invention relates to active substance combinations which contain an oximether derivative of formula

(I) (trifloxystrobin), and pyrirnethanil, and to their use as fungicides.

Fungicidal active compound combination

The present invention relates to a novel active compound combination which comprises a known oxime ether derivative and a known anilinopyrimidine and which is highly suitable for controlling phytopathogenic fungi.

5    It is already known that the oxime derivative 2-[a-{[(a-methyl-3-trifluoromethylbenzyl)imino]-oxy}-o-tolyl]glyoxylic acid methyl ester 0-methyloxime with the common name trifloxystrobin has fungicidal properties (cf. EP-A-0 460 575). The activity of this compound is good; however, it is sometimes unsatisfactory at low application rates. The preparation of this compound is likewise known from EP-A-0 460 575.

10    Moreover, it is known that the anilinopyrimidine 4,6-dimethyl-N-phenyl-2-pyrimidinamine with the common name pyrimethanil has fungicidal properties (cf. DD 00151404). The activity of this compound is good; however, it is sometimes unsatisfactory at low application rates. The preparation of this compound is likewise known.

Moreover, it is known that trifloxystrobin can generally be combined with various fungicides (for

15    example WO 97/00012, WO 97/00013). In a relatively long list, one of the possible mixing partners mentioned is inter alia pyrimethanil (Research Disclosure 41512 1998, pp. 1437- 1439).

Since the environmental and economic requirements imposed on modem-day fungicides are continually increasing, with regard, for example, to the spectrum of action, toxicity, selectivity,

application rate, formation of residues, and favourable preparability, and since, furthermore, there

20    may be problems, for example, with resistances, a constant task is to develop new fungicides which in some areas at least have advantages over their known counterparts.

The invention provides active compound combinations which in some aspects at least achieve the stated objectives.

It has  now  been  found  that  the  novel  active  compound  combination  comprising  2-[a-

25    {[(a-methyl-3-trifluoromethylbenzyl)imino]oxy }-o-tolyl]glyoxylic acid methyl ester 0-methyloxime of the formula (I)

(I)

0 'cH 3    (trifloxystrobin)


and

(2)    4,6-dimethyl-N-phenyl-2-pyrimidinamine  (reference: DD 00151404) of the formula (II)


(pyrimethanil)

5

possesses very good fungicidal properties.

Surprisingly, the fungicidal activity of the active compound combinations of the invention is substantially higher than the sum of the activities of the individual active compounds. fu other words there is an unforeseeable, true synergistic effect and not merely a supplementation of

10    activities.

A synergistic effect is particularly apparent when the active compounds are present in the active compound combinations according to the invention in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within a certain range.

15    Preferred mixing ratios are those where trifloxystrobin and pyrimethanil are present in a ratio of from 1:1.6 to 1:7.

Furthermore preferred mixing ratios are those where trifloxystrobin and pyrimethanil are present in a ratio of from 1:2 to 1:7.

Particularly preferred mixing ratios are those where trifloxystrobin and pyrimethanil are present in

20    a ratio of from 1:2.5 to 1:6.8.

Very particularly preferred mixing ratios are those where trifloxystrobin and pyrimethanil are present in a ratio of from I :3 to 1:6.6.

Furthermore very particularly preferred mixing ratios are those where trifloxystrobin and pyrimethanil are present in a ratio of from 1:3 to 1:4.

5    Furthermore very particularly preferred mixing ratios are those where trifloxystrobin and pyrimethanil are present in a ratio of from 1:3.1 to 1:3.7.

In a very particularly preferred mixing ratio, trifloxystrobin and pyrimethanil are present in a ratio of 1:3.3.

The  stated  active  compounds  trifloxystrobin  and  pyrimethanil  are  commercially  available.

10    Information on acquisition and, where appropriate, synthesis is found in C.D.S. Tomlin, The Pesticide Manual, 13th edition, British Crop Protection Council, Farnham 2003 and the literature cited therein. The active compound of the formula (I) is known (cf., for example, EP-A-460 575).

It is  evident  from  the  structural formula  of the  active  compound of the  formula  (I) that  the

compound may be present as E or Z isomer. Accordingly, the compound (I) may be present as a

15    mixture of different isomers or else in the form of a single isomer. Preferred is the compound of the formula (I) in which it is present as E isomer.

The active compound combinations according to the invention have potent microbicidal activity and can be employed for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.

20    By way of example, fungicides can be employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

By    way  of  example,  bactericides  can  be  employed  in  crop  protection  for  controlling

Pseudomonadaceae,    Rhizobiaceae,   Enterobacteriaceae,   Corynebacteriaceae   and   Strepto-

25    mycetaceae.

The active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmo-diophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.

Some pathogens causing fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation:

diseases caused by powdery mildew pathogens, such as, for example Blumeria species such as, for example, Blumeria graminis;

5    Podosphaera species such as, for example, Podosphaera leucotricha; Sphaerotheca species such as, for example, Sphaerotheca fuliginea; Uncinula species such as, for example, Uncinula necator;
diseases caused by rust pathogens such as, for example,

Gymnosporangium species such as, for example, Gymnosporangium sabinae

10    Hemileia species such as, for example, Hemileia vastatrix;

Phakopsora species such as, for example, Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species such as, for example, Puccinia recondita;

Uromyces species such as, for example, Uromyces appendiculatus;

diseases caused by pathogens from the Oomycetene group such as, for example,

15    Bremia  species such as, for example, Bremia lactucae;

Peronospora species such as, for example, Peronospora pisi or P. brassicae; Phytophthora species such as, for example, Phytophthora infestans; Plasmopara species such as, for example, Plasmopara viticola;

Pseudoperonospora species such as, for example, Pseudoperonospora humuli or

20    Pseudoperonospora cubensis;

Pythium species such as, for example, Pythium ultimum; leaf spot diseases and leaf wilts caused by, for example, Alternaria species such as, for example, Alternaria solani;

Cercospora species such as, for example, Cercospora beticola;

25    Cladiosporum species such as, for example, Cladiosporium cucumerinum; Cochliobolus species such as, for example, Cochliobolus sativus

(conidial form: Drechslera, syn: Helminthosporium);

Colletotrichum species such as, for example, Colletotrichum lindemuthanium;

Cycloconium species such as, for example, Cycloconium oleaginum; Diaporthe species such as, for example, Diaporthe citri;

Elsinoe species such as, for example, Elsinoe fawcettii; Gloeosporium species such as, for example, Gloeosporium laeticolor;

5    Glomerella species such as, for example, Glomerella cingulata; Guignardia species such as, for example, Guignardia bidwelli; Leptosphaeria species such as, for example, Leptosphaeria maculans;

Magnaporthe species such as, for example, Magnaporthe grisea;

Mycosphaerella species such as, for example, Mycosphaerella fijiensis;

10    Phaeosphaeria species such as, for example, Phaeosphaeria nodorum; Pyrenophora species such as, for example, Pyrenophora teres; Ramularia species such as, for example, Ramularia collo-cygni; Rhynchosporium species such as, for example, Rhynchosporium secalis;

Septoria species such as, for example, Septoria apii;

15    Typhula species such as, for example, Typhula incarnata; Venturia species such as, for example, Venturia inaequalis; root and stem diseases caused by, for example,

Corticium species such as, for example, Corticium graminearum;

Fusarium species such as, for example, Fusarium oxysporum;

20    Gaeumannomyces species such as, for example, Gaeumannomyces graminis; Rhizoctonia species such as, for example, Rhizoctonia solani;

Tapesia species such as, for example, Tapesia acuformis;

Thielaviopsis species such as, for example, Thielaviopsis basicola;

ear and panicle diseases (including maize cobs), caused by, for example,

25    Alternaria species such as, for example, Alternaria spp.; Aspergillus species such as, for example, Aspergillus flavus; Cladosporium species such as, for example, Cladosporium spp.; Claviceps species such as, for example, Claviceps purpurea;

Fusarium species such as, for example, Fusarium culmorum;

Gibberella species such as, for example, Gibberella zeae;

Monographella species such as, for example, Monographella nivalis;

diseases caused by smuts such as, for example,

5    Sphacelotheca.species such as, for example, Sphacelotheca reiliana; Tilletia species such as, for example, Tilletia caries;

Urocystis species such as, for example, Urocystis occulta; Ustilago species such as, for example, Ustilago nuda; fruit rots caused by, for example,

10    Aspergillus species such as, for example, Aspergillus flavus; Botrytis species such as, for example, Botrytis cinerea; Penicillium species such as, for example, Penicillium expansum; Sclerotinia species such as, for example, Sclerotinia sclerotiorum;

Verticilium species such as, for example, Vertic ilium alboatrum;

15    seed- and soil-borne rot and wilts, and seedling diseases, caused by, for example, Fusarium species such as, for example, Fusarium culmorurn;

Phytophthora species such as, for example, Phytophthora cactorum; Pythium species such as, for example, Pythium ultimum; Rhizoctonia species such as, for example, Rhizoctonia solani;

20    Sclerotium species such as, for example, Sclerotium rolfsii; cankers, galls and witches' broom disease, caused by, for example, Nectria species such as, for example, Nectria galligena;

wilts caused by, for example,

Monilinia species such as, for example, Monilinia laxa;

25    deformations of leaves, flowers and fruits, caused by, for example, Taphrina species such as, for example, Taphrina deformans; degenerative diseases of woody species, caused by, for example, Esca species such as, for example, Phaemoniella clamydospora;

diseases of inflorescences and seeds, caused by, for example, Botrytis species such as, for example, Botrytis cinerea; diseases of the plant tubers, caused by, for example, Rhizoctonia species such as, for example, Rhizoctonia solani;
5    diseases caused by bacterial pathogens such as, for example:

Xanthomonas species such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species such as, for example, Pseudomonas syringae pv. lachrymans; Erwinia species such as, for example, Erwinia amylovora;

The following diseases of soya beans can preferably be controlled:

10    fungal diseases on leaves, stems, pods and seeds caused by, for example,

alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and
blight  (Cercospora  kikuchii),  choanephora  leaf  blight  (Choanephora  infundibulifera  trispora

(syn.)),    dactuliophora   leaf   spot   (Dactuliophora   glycines),   downy   mildew   (Peronospora

15    manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola),

powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot

20    (Corynespora cassiicola)

fungal diseases on roots and the stem base caused by, for example,

black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium

semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmo-

25    spora (Neocosmopspora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperrna), brown stem rot (Phialophora gregata), pythium rot (Pythium aphaniderrnatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay,

and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia

30    southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

The active compounds according to the invention also show a strong invigorating action in plants. Accordingly, they are suitable for mobilizing the internal defences of the plant against attack by unwanted microorganisms.

In the present context, plant-invigorating (resistance-inducing) compounds are to be understood as

5    meaning substances which are capable of stimulating the defence system of plants such that, when the treated plants are subsequently inoculated with unwanted microorganisms, they display substantial resistance to these microorganisms.

In the present case, unwanted microorganisms are to be understood as meaning phytopathogenic

fungi and bacteria. The compounds according to the invention can thus be used to protect plants

10    within a certain period of time after treatment against attack by the pathogens mentioned. The period of time for which this protection is achieved generally extends for 1 to 10 days, preferably 1 to 7 days, from the treatment of the plants with the active compounds.

The  active  compound  combinations  according  to  the  invention  are  particularly  suitable  for

controlling mildew and leaf blotch diseases, fruit and blossom rots, storage diseases and secondary

15    infections by Aspergillus/Penicillium etc.

The active compound combinations according to the invention are particularly suitable for use in viticulture, fruit cultivation, in plantation crops, in the cultivation of vegetables and in leguminous plants.

The fact that the active compound combinations are well tolerated by plants at the concentrations

20    required for controlling plant diseases permits the treatment of above-ground 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 are also suitable for increasing the harvest yield. In addition, they show reduced toxicity and are well tolerated by plants.

25    According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and

genetic engineering methods or combinations of these methods, including the transgenic plants and

30    including plant cultivars which can or cannot be protected by plant breeders' certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves,

needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested material and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

As  already  mentioned above,  it  is possible to treat all plants and their parts according to the

5    invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically

Modified Organisms), and parts thereof, are treated. The term "parts" or "parts of plants" or "plant

10    parts" has been explained above.

Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having new properties ("traits") and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, bio- and genotypes.

15    Depending on the plant species or plant cuhivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a

widening  of  the  activity  spectrum  and/or  an  increase  in  the  activity  of  the  substances  and

compositions  which  can  be  used  according  to  the  invention,  better  plant  growth,  increased

20    tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected.

25    The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are preferably to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly advantageous useful properties ("traits") to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content,

30    increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance


of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape.

5    Traits that are particularly emphasized are increased defence of the plants against insects by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryiA(a), CryiA(b), CryiA(c), CryiiA, CrylllA, CryiiiB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants against

10    fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene). The genes which impart the desired traits in

15    question can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton,

soya  beans),  KnockOut®   (for  example  maize),  StarLink®   (for  example  maize),  Bollgard®

(cotton), Nucoton® (cotton)  and NewLeaf®  (potato). Examples of herbicide-tolerant plants which

20    may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant

plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned also

25    include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars which have these genetic traits or genetic traits still to be developed, and which will be developed and/or marketed in the future.

The plants listed can be treated according to the invention in a particularly advantageous manner

with the active compound mixtures according to the invention. The preferred ranges stated above

30    for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the mixtures specifically mentioned in the present text.

The  treatment  of the  plants  and  parts  of plants  according  to  the  invention  with  the  active

compounds  is  carried out  directly  or  by  action  on their environment,  habitat  or  storage  area

35    according  to  customary  treatment  methods,  for  example  by  dipping,  spraying,  evaporating,

atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating.

The active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols

5    and microencapsulations in polymeric substances and in coating compositions for seeds, and also UL V 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

10    dispersants, and/or foam formers. If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: 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

15    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 or dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at standard temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers

20    are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite 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, pumice, marble, sepiolite and dolomite, or else synthetic

granules  of  inorganic  and organic  meals,  and granules  of organic  material  such  as  sawdust,

25    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, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.

30    Tackifiers such as carboxymethylcellulose, 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 possible additives are 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.

5    The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

The  active  compound  combinations  according  to  the  invention  can,  as  such  or  in  their

formulations,  also  be  used  in  a  mixture  with  known  fungicides,  bactericides,  acaricides,

nematicides  or  insecticides,  to  broaden,  for  example,  the  activity  spectrum  or  to  prevent

10    development of resistance.

Fungicides:

1.    Nucleic acid synthesis inhibitors

benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl,

hymexazol, metalaxyl-M, ofurace, oxadixyl, oxolinic acid

15    2. Mitosis and cell division inhibitors

benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide

3. Inhibitors of the respiratory chain

3.1 Complex 1

20    diflumetorim

3.2 Complex 11

boscalid, carboxin, fenfuram, flutolanil, furametpyr, mepronil, oxycarboxin, penthiopyrad,

thifluzamide

3.3 Complex Ill

azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, pyraclostrobin, picoxystrobin

3.4 Decouplers

5    dinocap, fluazinam

3.5 ATP production inhibitors

fentin acetate, fentin chloride, fentin hydroxide, silthiofam

4. Amino acid and protein biosynthesis inhibitors

andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim

10    5. Signal transduction inhibitors fenpiclonil, fludioxonil, quinoxyfen

6. Lipid and membrane synthesis inhibitors

chlozolinate, iprodione, procymidone, vinclozolin

pyrazophos, edifenphos, iprobenfos (ffiP), isoprothiolane

15    tolclofos-methyl, biphenyl

iodocarb, propamocarb, propamocarb hydrochloride

7. Inhibitors of ergosterol biosynthesis

fenhexamid,

azaconazole,    bitertanol,    bromucooazole,    cyproconazole,    diclobutrazole,    difenoconazole,

20    diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole,


metconazole, myclobutanil, paclobutrazol, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, voriconazole, imazalil, imazalil sulphate, oxpoconazole, fenarimol, flurprimidol, nuarimol, pyrifenox, triforine, pefurazoate, prochloraz, triflumizole, viniconazole,

5    aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, spiroxamine, naftifine, pyri buticarb, terbinafine
8. Cell wall synthesis inhibitors

benthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim,

validamycin A

10    9. Melanin biosynthesis inhibitors

capropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole

10. Resistance inductors

acibenzolar-S-methyl, probenazole, tiadinil

11. Compounds with multisite activity

15    captafol, captan, chlorothalonil, copper salts, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine copper and Bordeaux mixture, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet, fosetyl-Al, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb,

metiram, metiram zinc, propineb, sulphur and sulphur preparations comprising calcium polysulphide, 20 thiram, tolylfluanid, zineb, ziram

12. Unknown

amibromdol, benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, chloropicrin, cufraneb, cyflufenarnid, cymoxani~ dazomet, debacarb, diclomezine, dichlorophen, dicloran, difenzoquat, difenzoquat methylsulphate, diphenylamine, ethaboxam, ferirnzone, flumetover, flusulfamide,

25    fluopicolide, fluoroimide, hexacblorobenzene, 8-hydroxyquinoline sulphate, irumamycin, methasulfocarb, metrafenone, t.nethyl isothiocyanate, mildiomycin, natamycin, nickel


dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, 2-phenylphenol and salts, piperalin, propanosine-sodium, proquinazid, pyrrolnitrin, quintozene, tecloftalam, tecnazene, triazoxide, trichlarnid, zarilarnid and 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, N-(4-chloro-2-nitrophenyl)-N-ethyl-4-

5    methylbenzenesulphonarnide, 2-arnino-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N-(2,3-dihydro-1, 1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxarnide, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, cis-1-( 4-chlorophenyl)-2-( lH-1,2,4-triazol-1-yl)cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4-[[[[1-[3-

( trifluoromethyl)phenyl] ethylidene] amino]oxy]methyl]phenyl]-3H-1 ,2,3-triazol-3 -one ( 1853 36-79-2),

10    methyl 1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-irnidazole-5-carboxylate, 3 ,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl 2-[[[ cyclopropyl [( 4-methoxyphenyl )imino] methyl] thio]methy1]-a:-(methoxymethylene)benzacetate, 4-chloro-a:-propynyloxy-N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]benzacetarnide, (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide, 5-chloro-7-(4-

15    methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[l ,2,4]triazolo[ 1,5-a ]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-arnine, 5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, N-[1-(5-

bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinarnide, N-(5-bromo-3-chloropyridin-2-yl)methyl-2,4-dichloronicotinarnide, 2-butoxy-6-iodo-3-propylbenzopyranon-4-one, N-{ (Z)-

20    [( cyclopropylmethoxy)imino] [6-( difluoromethoxy)-2,3-difluorophenyl] methyl)-2-benzacetarnide, N-(3-ethyl-3 ,5,5-trimethylcyclohexy1)-3-formylarnino-2-hydroxybenzarnide, 2-[[[ [ 1-[3 -( 1-fluoro-2-phenylethyl)oxy]phenyl]ethylidene ]amino]oxy]methyl]-a-(methoxyimino)-N -methyl-aE-benzacetarnide, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl)-2-(trifluoromethyl)benzamide, N -(3 ',4'-dichloro-5-fluorobipheny1-2-yl)-3-(difluoromethyl )-1-methyl-1H-pyrazole-4-carboxarnide, N-

25 (6-methoxy-3-pyridinyl)cyclopropanecarboxarnide, 1-[(4-methoxyphenoxy)methyl]-2,2-dirnethylpropyl-lH-imidazole-1-carboxylic acid, 0-[ 1-[(4-methoxyphenoxy)methyl]-2,2-dirnethylpropyl]-lH-imidazole-1-carbothioic acid, 2-(2-{ [6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl] oxy) phenyl)-2-(methoxyirnino )-N -methylacetarnide

Bactericides:

30    bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbarnate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalarn, copper sulphate and other copper preparations.

Insecticides I acaricides I nematicides:

1.    Acetylcholinesterase (AChE) inhibitors

1.1    carbamates (for example alanycarb, aldicarb,  aldoxycarb, allyxycarb, aminocarb,  azamethi-

phos,  bendiocarb,  benfuracarb,  bufencarb,  butacarb,  butocarboxim,  butoxycarboxim,  carbaryl,

5    carbofuran, carbosulfan, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb)

1.2  organophosphates   (for  example  acephate,   azamethiphos,  azinphos   (-methyl,   -ethyl), 10    bromophos-ethyl,    bromfenvinfos    (-methyl),    butathiofos,    cadusafos,    carbophenothion, chlorethoxyfos,   chlorfenvinphos,   chlormephos,   chlorpyrifos   (-methyV-ethyl),   coumaphos, cyanofenphos,   cyanophos,   chlorfenvinphos,   demeton-S-methyl,   demeton-S-methylsulphone, dialifos, diazinon, dichlofenthion,  dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion,

15    fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl 0-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyV-ethyl), phenthoate, phorate, phosalone,
phosmet,    phosphamidon,   phosphocarb,   phoxim,   pirimiphos   (-methyV-ethyl),   profenofos,

20    propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion)

2.    Sodium channel modulators/blockers of voltage-gated sodium channels

2.1    pyrethroids (for example acrinatbrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin,

25    bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyflu-thrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin OR-isomer), esfenvalernte, etofenprox, fenfluthrin, fenpropathrin, fenpyritbrin, fen-valerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-

30 cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (lR-isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins (pyrethrum))
 



- 17-

2.2 oxadiazines (for example indoxacarb)

3.    Acetylcholine receptor agonists/antagonists

3.1    chloronicotinyls/neonicotinoids (for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam)

5    3.2 nicotine, bensultap, cartap

4.    Acetylcholine receptor modulators

4.1    spinosyns (for example spinosad)

5.    Antagonists ofGABA-gated chloride channels

5.1    cyclodiene organochlorines (for example camphechlor, chlordane, endosulfan, gamma-HCH, 10 HCH, heptachlor, lindane, methoxychlor)

5.2    fiproles (for example acetoprole, ethiprole, fipronil, vaniliprole)

6.    Chloride channel activators

6.1    mectins (for example abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, milbemectin, milbemycin)

15    7. Juvenile hormone mime tics

(for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene)

8.    Ecdyson agonists/disruptors

8.1    diacylhydrazines (for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide)

20    9. Chitin biosynthesis inhibitors

9.1    benzoylureas (for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron)

9.2    buprofezin
 

25    9.3 cyrornazine
 



- 18-

10.    Inhibitors of oxidative phosphorylation, ATP disruptors

10.1    diafenthiuron

10.2    organotins (for example azocyclotin, cyhexatin, fenbutatin-oxide)

11.    Decouplers of oxidative phosphorylation acting by interrupting the H-proton gradient

5    11.1 pyrroles (for example chlorfenapyr)

11.2    dinitrophenols (for example binapacryl, dinobuton, dinocap, DNOC)

12.    Site-] electron transport inhibitors

12.1    METis (for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad)

10    12.2 hydramethylnone

12.3    dicofol

13.    Site-11 electron transport inhibitors

13.1    rotenone

14. Site-Ill electron transport inhibitors

15    14.1 acequinocyl, fluacrypyrim

15. Microbial disruptors of the insect gut membrane

Bacillus thuringiensis strains

16.    Inhibitors offat synthesis

16.1    tetronic acids (for example spirodiclofen, spiromesifen)

20    16.2 tetramic acids [for example 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate (alias: carbonic acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl ester, CAS Reg. No.: 382608-10-8) and carbonic acid, cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl ester (CAS Reg. No.: 203313-25-1)]


17. Carboxamides

(for example flonicamid)

18. Octopaminergic agonists

(for example amitraz)

5    19.1nhibitors ofmagnesium-stimulatedATPase

(for example propargite)

20. Phthalamides

(for    example    N    2    1   
            -[ 1, 1-dimethyl-2-(methylsulphonyl)ethyl]-3-iodo-N -[2-methyl-4-[ 1,2,2,2-   

tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide  (CAS  Reg.  No.:  272451-

10    65-7), flubendiamide)

21. Nereistoxin analogues

(for example thiocyclam hydrogen oxalate, thiosultap-sodium)

22. Biologicals, hormones or pheromones

(for  example  azadirachtin,  Bacillus  spec.,  Beauveria  spec.,  Codlemone,  Metarrhizium  spec.,

15    Paecilomyces spec., Thuringiensin, Verticillium spec.)

23.    Active compounds with unknown or unspecific mechanisms of action

23.1    fumigants (for example aluminium phosphide, methyl bromide, sulphuryl fluoride)

23.2    selective antifeedants (for example cryolite, flonicarnid, pymetrozine)

23.3    mite growth inhibitors (for example clofentezine, etoxazole, hexythiazox)

20    23.4 arnidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, chinomethi-onat, chlordimeforrn, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, di-cyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerirn, flutenzin, gossyplure, hydramethyl-none, japonilure, metoxadiazone, petroleum, piperonyl butoxide, potassium oleate, pyrafluprole, pyridalyl, pyriprole, sulfluramid, tetradifon, tetrasul, triarathene, verbutin,

3) and the corresponding 3-endo-isomer (CAS Reg. No. 185984-60-5) (cf. WO 96/37494, WO 98/25923), and preparations which comprise insecticidally active plant extracts, nematodes, fungi or viruses.

A    mixture   with  other  known  active  compounds,   such  as  herbicides,   safeners  and/or

5    semiochemicals, or with fertilizers and growth regulators is also possible.

The compounds (I) and (II) can be applied simultaneously, and, if so, either together or separately, or in succession; in the case of separate application, the sequence generally has no consequence for the control outcome.

The active compound combinations can be used as such, in the form of their formulations or the

10    use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. Application is carried out in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, dry dressing, moistened dressing, wet dressing, slurry dressing or encrusting.

When using the active compound combinations according to the invention, the application rates

15    can be varied within a relatively wide range, depending on the kind of application. For the treatment of parts of plants, the active compound combination application rates are generally between 0.1 and 10 000 g/ha, preferably between 10 and 1000 glha. For seed dressing, the active compound combination application rates are generally between 0.001 and 50 g per kilogram of

seed, preferably between 0.01  and 10 g per kilogram of seed. For the treatment of the soil, the

20    active compound combination application rates are generally between 0.1 and 10 000 glha, preferably between 1 and 5000 glha.

The good fungicidal activity of the active compound combinations according to the invention is

demonstrated  by  the  examples  below.  Whereas  the  individual  active  compounds  exhibit

weaknesses in fungicidal activity, the combinations display an activity which goes beyond a simple

25    summation of activities.

A synergistic effect is always present in fungicides when the fungicidal activity of the active compound combinations is greater than the sum of the activities of the active compounds applied individually.

The expected activity for a given combination of two active compounds can be calculated in

30    accordance with S.R. Colby ("Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 15 (1967), 20-22) as follows:
If

X    denotes the efficacy when using active compound A at an application rate of ill glha,

y    denotes the efficacy when using active compound B at an application rate of n_glha, and

E    denotes the efficacy when using active compounds A and B at application rates of ill and !!.

5    glha,

then

X•Y
E=X+Y-
100

The efficacy here is determined in %. 0% denotes an efficacy which corresponds to that of the control, while an efficacy of 100% means that no infestation is observed.

10    If the actual fungicidal activity is greater than that calculated, then the activity of the combination is superadditive: in other words, a synergistic effect is obtained. In this case the efficacy actually observed must be greater than the value calculated using the above-indicated formula for the expected efficacy (E).

Another method of determining synergistic effects is offered by the Tammes model (Neth. J. Plant

15    Path. 70 (1964) 73-80), where, for example, the theoretical dosage for an efficacy of 90% is determined and is compared with the dosage actually required.

The invention is illustrated by the following examples. The invention is not, however, limited to the examples.

    Example   
    Sphaerotheca test (cucumber) I protective
    Solvents:    24.5 parts by weight of acetone
        24.5 parts by weight of dimethylacetamide
5    Emulsifier :    1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination with water is diluted with water to the desired

10    concentration.

To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at about 23°C and a relative atmospheric humidity of about 70%.

15    Evaluation is carried out 7 days after inoculation. Here, 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infestation is observed.

The invention is illustrated by the following examples.

The  table  below  shows  clearly that  the  activity  found  for  the  active  compound  combination

according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

20    The synergism found is surprisingly clearly pronounced for the mixing ratios according to the invention, the mixing ratio (I) to (II) of 1:3.3 having the most pronounced synergistic effect.
TABLE

Spbaerotheca test (cucumber) I protective


Active compound    Active  compound    % efficacy
    application rate  in   
    ppm   
       
Trifloxystrobin    4    10



    ~ .,...o           
    N           
        o........._       
        0       
    F           
        3.3       
Pyrimethanil        0   
    Q    6.6    0   
        13.2    0   
        26.4    0   
    NH           
    N~N    52.8    0   
               
A)l..........

TABLE

Sphaerotheca test (cucumber) I protective


Mixture according to the inventiQo;

            Mixing ratio    Active    Actual efficacy    Expected value       
                    compound        calculated using       
                    application    rate    Colby's formula       
                    in    m               
        Trifloxystrobin        1:0.83    4    53    10       
        +    }    +    }           
        Pyrimethanil        3.3               
                               
                               
        Trifloxystrobin    1:1.65    4    57    10       
        +    }    +    }           
        Pyrimethanil        6.6               
                               
        Trifloxys trobin        1:3.3    4    73    10       
        +    }    +    }           
        Pyrimethanil        13.2               
                               
                               
        Trifloxystrobin    1:6.6    4    65    10       
        +    }    +    }           
        Pyrimethanil        26.4               
                               
                               
        Trifloxystrobin    1:13.2    4    57    10       
        +    }    +    }           
        Pyrimethanil        52.8               
                               
                                   


The test demonstrated synergism between trifloxystrobin and pyrimethanil.

Patent claims

1.    Active compound combination comprising a compound of the formula <n


0 'CH3

and
5    (2)    a compound of the formula (ill)

(pyrimethanil)

2.    Active compound combination according to Claim 1, characterized in that in the active compound combination the weight ratio of active compound of the formula (I) to active compound of the formula (II) is from 1:1.6 to 1:7.

10    3. Active compound combination according to Claim 1 or 2, characterized in that in the active compound combination the weight ratio of active compound of the formula (I) to active compound of the formula (II) is from 1: 2.5 to 1 :6.8.

4.    Active compound combination according to any of Claims 1 to 3, characterized in that in the active compound combination the weight ratio of active compound of the formula (I) to
15    active compound of the formula (II) is from 1:3 to 1:4.

5.    Method for controlling phytopathogenic fungi, characterized in that an active compound combination according to one or more of Claims 1 to 4 is allowed to act on the fungi and/or their habitat or the plants, plant parts, seeds, soils, areas, materials or spaces to be kept free from them.

6.    Method according to Claim 5, characterized in that the compound (I) according to Claim 1 and the compound <m according to Claim 1 are applied simultaneously, that is together or separately, or in succession.

7.    Propagation material, coated with an active compound combination according to one or
5    more of Claims 1 to 4.

8.    Fungicidal compositions, comprising an amount of an active compound combination as defined in one or more of Claims 1 to 4.

9.    Use of the active compound combination or composition as defined in one or more of Claims 1 to 4 and 8 for controlling fungi.

10.    Process for preparing fungicidal compositions, characterized in that the active compounds of the active compound combinations according to one or more of Claims 1 to 4 are mixed with extenders and/or surfactants.

Fungicidal active compound combinations



Abstract



Active compound combinations comprising an oxime ether derivative of tbe formula (I)
 

0 'cH3
 
(I)

(trifloxystrobin) and pyrimetbanil and their use as fungicides are described.

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