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(12) PATENT
(51) Int.C1.A: 01N 37/150, 47//04, 01P 3//00
(21) Application    KE/P/2008/00762    (84) WO No. WO 2007/068367 Al
Number:    21/06/2007
(22)Filing Date:    04/12/2006
(31)Priority Number: 102005060281.9    (32) Date: 16/12/2005 (33) Country: DE
(73)    Owner(s): BAYER CROPSCIENCE AG of Alfred-Nobel-Str 50, 40789 Monheim, Germany
(72) Inventor(s)
(74)    Agent/address for correspondence:    WACHENDORFF-NEUMANN, Ulrike; DAHMEN, Peter ; HAUSER-HAHN, Isolde and
WITZENBERGER, Albert
Kaplan & Stratton Advocates, P.O. Box 40111-00100, Nairobi

(54) Title:    FUNGICIDAL ACTIVE COMPOUND COMBINATION.
(57)    Active compound combinations comprising an oxime ether derivative of the formula
Abstract:    (1) and captan and their use as fungicides are described.
 
Funeicidal active compound combination.
The present invention relates to a novel active compound combination which comprises a known oxime ether derivative and a known bis-thiocarbamate and which is highly suitable for controlling phytopathogenic fungi.
5 - It is already known that the oxime derivative 24a-([(a—methyl-3-trifluoromethyl-benzypimino]- oxy)-o-toly1]-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'sometirnes 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 phthalimide 3a,4,7,7a-tetrahydro-2-Ktrichloromethyl)thiol-1H-isoiridole-1,3(21-1)-dione with the Common Name captan has fungicidal properties ' (cf. -US 2553770). 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 propineb (Research Disclosure 41512 1998, pp. 1437 — 1439).
Since the environmental and economic requirements imposed on modern-day fungicides are
continually increasing, with regard, for example, to the spectrum olaction, 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 _Compbtind combinations whielf in in some aspects at least achieve • the stated Objectives. -
It has been found that the novel active compound combination comprising 2-[a-{[(a—methyl-3¬25 trifluoremethY1-benzypiniinoioxy)-o-tolY1)-glyoxylic acid methyl ester' .0-methyloxime of the formula (I)
 
-2-
 

 
and
(2)    3a,4,7,7a-tetrahydro-2-Rtrichloromethyl)thio1-1H-isoindole-1,3(2H)-dione (reference: US
2553770) of the formula (11)
 
N—S
CCI3
(captan)
 
has 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. In 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. tlowevoic.the weight
ratios of the active compounds in the active. compound combinations.can be varied within„a..Certain
15 Preferred mixing ratios are those where:triflOxystrobin and captan are present in a ratio of from 10 to 1:19.
Furthermore preferred mixing ratios are those where trifloxystrobin and :captan are fireSe0 in a • ratio of from 1
Paiticularly preferred mixing ratios are those where trifloxystrobin and captan are present in a ratio 20    of from 1 : 12 to 1:18.
 
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Very particularly preferred mixing ratios are those where trifloxystrobin and captan are present in a ratio of from 1 : 13 to 1:17.
Furthermore very particularly preferred mixing ratios are those where trifloxystrobin and captan are present in a ratio of from 1 : 13 to 1:16.
5    Furthermore very particularly preferred mixing ratios are those where trifloxystrobin and captan
are present in a ratio of from 1 : 14 to 1:16.
In a very particularly preferred mixing ratio, trifloxystrobin and captan are present in a ratio of 1:15.
The statedactiVe compounds trifloxystrObhi and captan are' commercially. available. Information
10    on acquisition and where appropriate; synthesis are 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 khown (cr., 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 thelotiri 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 Fungicides can be.employed in crop protection for controlling Plasmodiciphoromytetes, Oomycetes, ChytridioinyCetes,:Zygotnycetes:AscOmvcetes_ Rasidinmvnetes and DeuteroinYcetes. Bactericides can be employed in crop protection for controlling PsendOtnOnadaceae, Rhizobiaceie,
.    .
Enterobacteriaceae, Corynebacteriaceae and.Streptomycetaceae, .
The active cornioned combinations according to the invention have very good fungicidal
25 properties and can be". `employed for controlling phytopathogenic fungi, such as Plasmo-
..
diophoromycetes, Ocinnicetes, Chvtridioinircetes. • Zvaomvcetes. ASComycetes, Dasidioniycetes, 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:
 
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diseases caused by powdery mildew pathogens, such as, for example Blumeria species such as, for example, Blumeria graminis;
Podosphaera species such as, for example, Podosphaera leucotricha;
Sphaerotheca species such as, for example, Sphaerotheca fuliginea;
5 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
Hemileia species such as, for example, Hemileia vastatrix;
Phakopsora speties such as, for example, Phakopsora pachyrhizi and Phakoosora meibomiae;
10 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,
Bremia species such as, for example, Bremialactucae;
PeronospOra species such as, for example, Peronospora pisi or P. brassicae;
15 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 Pseudoperonospora cubensis;
Pythium Species such as, for example, Pythium ultimum;
20 • leaf spot diseases and leaf wilts caused by,. for example, Alternaria species such as, for example,Alternaria solani; Cercospora species such as, for ixampli,•Cercospora beticola;
Cladiosporum species such as, for exaMple., Cladiospcirium cucumerinum;
Cochliobolus species such as, for example, Cochliobolus sativus 25 (conidial fOrm: Drechslera, syn : Helminthosporium);
Colletotrichum species such as, for example, Colletotrichum lindemtithaniuni;
Cycloconium species such as, for example, Cycloconium oleagintun; Diaporthe species such as, for example, Diaporthe citri;
 
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Elsinoe species such as, for example, Elsinoe fawcettii;
Gloeosporium species such as, for example, Gloeosporium laeticolor; Glomerella species such as, for example, Glomerella cingulata; Guignardia species such as, for example, Guignardia bidwelli;
5 Leptosphaeria species such as, for example, Leptosphaeria maculans;
Magnaporthe species such as, for example, Magnaporthe grisea;
Mycosphaerella species such as, for example; Mycosphaerella fijiensis; Phaeosphaeria species such as, for example; Phaeosphaeria nodorum; ..Pyrenophora species such as, for example, Pyienophora teres;
10 Ramularia species such as for example, Rimularia collo-cygni;
RhYnchospOeium species such as, for example, Rhynchosporium secalis; Septoria SpeCieS such as, for example, Septoria apii;
Typhula SpeCies such as; for example, Typhtila incarnata;
Venturia specieS such as, for example, Venturia inaequalis; 15 root and stem diseases caused by, for example,
Corticium species such as, for example, Corticium graminearum; Fusariunt species such as, for example, fusarium oxysporum;
Gaeumannomyces species such as,' for example, Gaeumannomyces graminis; Rhizoctonia species such as for example, ithizoctonia solani;
20 Tapesiaspecies:kich'as; for example, Tapesia acttforinis;  ThielaViopsis'sPeciei such as,.for eXamPle,-Tliielaviapsis basieola;
ear and panicle diseases (including maize CobS);paused by foi example, Alternaria species such as, for example, Alternafinspp.;
Aspergillus species such as for example, Aspergillus flavus;

25 ' Cladosporium species such as, for example; Cladoiporium spp.; Claviceps species such as, for example, Claviceps purpurea; Ftisarimn specieS such as, for example, FusarinmCulmonun; Gibberella species such as, for example, Gibberella zeae;
 
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Monographella species such as, for example, Monographella nivalis; diseases caused by smuts such as, for example,
Sphacelotheca species such as, for example, Sphacelotheca reiliana; Tilletia species such as, for example, Tilletia caries;
5 Urocystis species such as, for example, Urocystis occulta;
Ustilago species such as, for example, Ustilago nuda;
fruit rots caused by, for example;
Aspergillus species such as, for example, Aspergillus flavus; Botrytis species such as, for example, Botrytis cinerea;
10 Penicillium species such as, for example, Penicillium expansum; Sclerotinia species such as, for example, Sclerotinia sclerotiorum; Verticilium species such as, for example, Verticilium alboatrum;
seed- and soil-borne rot and wilts, and seedling diseases, caused by, for example,. Fusarium species such as, for example, Fusarium culmorum;
15 Phytophthora species such as, for example, Phytophthora cactorum; Pythium species such as, for example, Pythium ultimum; Rhizoctonia species such as, for example, Rhizoctonia solani; Sclerotiwn species such as, for example, Sclerotium rolfsii; Cankers, galls and witches' brOom disease, caused by, for example,
20 Nedtrias*iis such as, for example, Nectria galligena;
Wilts caused by, for eXaMple,
.    •
Monilinia species such as for eXaniple,•Monilinia laxa;
deformations of leaVes, flowers and fruits, caused by, for example; Taphrina species such as for example, Taphrina deformanS;
25 degenerative diseases of woody species, caused by, for example,


Esca species such as, for example, Thaemoniella clamydospora; diseases of inflorescences and seeds, caused by, for example, Botrytis species such as, for example, Botrytis cinerea;
 
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diseases of the plant tubers, caused by, for example,
Rhizoctonia species such as, for example, Rhizoctonia solani;
diseases caused by bacterial pathogens such as, for example:
Xanthomonas species such as, for example, Xanthomonas campestris pv. oryzae;
5 Pseudomonas species such as, for example, Pseudomonas syringae pv. lachrym- ans; Erwinia species such as, for example, Erwinia amylovora;
The following diseases of soybeans can preferably be controlled:
Fungal diseases on leaves, stems, pods and seeds caused by, for example,
alternaria . leaf spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum
10 . gloeasponiides dernatiunt var. truncaturn), brown spot (Septoria glycines), cercospora leaf spot and . blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora. (syn.)), dactuliophora leaf spot (Dactuliophera glycines),• downy mildew (Peronospora manahitrica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina phyllostica leaf•spot (Phyllosticta sojaecola),
15 powdery mildew (Microsphaera diffuSi), pyrenochaeta leaf spot (Pyienochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi), scab ($phaoeldma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola)
fungal diseases on roots and the stem baSe caused by,.for example,
20 black root rot (Caloncctria crotalariac), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium :Okysporum, Fusarium orthoCeins, .Fusarium • semiteetum,.Fusaiinmeginseti), mycciteptOdiscHus root rot (Mycoleptodiscits terrestria); neOcOStrio-• . sPora (NeocostriopspOra ,vasirifeeta), pod and stem blight (Diaporthe phaseolortim);• stem canker (Diaporthe phaseolorum • var. caulivora), pheophthota..rot (Fhytophihora .inagisperina), .btOWn
25 stein' tin _ (Phialophora gregata), pythium rot "(PYilduin :aphanideitnattirri, Pythium inigulare; -Pythium debaryanum, Pythium myriotylum, Pythium ultirnum), rhizoctonia root rot,. stem decay, . and.damping-off(Rhizoctoiiia solani), sclerOthila sientdeCay(Sclerotiniasclet.otiorum), sclerOtinia sOuthern blight (Selerotinia thielavio Psis ro.Otrcit (Thielaviopsis.basicola).1
The active comPounda according to the invention also show a strong invigorating action in plants. 30 Accordingly, they are suitable for mobilizing the internal defences of the plant against Attack by unwanted microorganisms.
 
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In the present context, plant-invigorating (resistance-inducing) compounds are to be understood as 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 micronroanismc
5 In the preaefit 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 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.
10 . The active compound combinations according to the invention are particularly suitable for controlling mildew and leaf blotch diseases, fruit and blossom tots, storage diseases and secondary infections by ASpergillus/Penicillium etc..
The active, compound combinations according to the invention are particularly suitable for use in
vitietiltUre, friiit cultiVation; in plantation Crops, in the cultivation of vegetables and in leguminous •
15    .plants.
The fact mat the active compound combinations are well tolerated by plants at the Concentrations required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. The actiNie compound combinations according to the invention can be used for foliar* application or else as seed dresSines.
20 The active compound Conabinations according to the invention are also suitable for increasing the harvest yield. In addition, they show reduced toxicity and are well tolerated by nlants.
According; to. ille;inyention;;_.it pOiaibli.io'.treat all plants and parts  of plants,' Plants: are to he.
underatood here as meaning .all•Plantiand .plant Populations; auch'is desired and undeSired plaids or .crop planta.(including naturally occurring crop plants). Crop plants can be plants which
25 can be obtained by conventional breeding and optimization 'methods or by biotechnological and
genetic engineering Methodi or combinationa. of these methods; including the transgenid, plants and
•    .
inchiding plant cUltiVais which can Or cannot Cie prOteeted by plant bieeders' certificates. Parts of
plants are to he understood as meaning all above-ground and below-ground parts and Organs of
Plants, such as Shot* leaf, flower    _root, examples which may be MentiOned being* leaves,
30 needles; stems, thinks, flowers, fruit-bOdies, fruits and seeds and also roots, tubera and rhizomes. Parts of plants also include harvested material and vegetative and generative propagation material, for example seedlings, tubers; rhizomes, cuttings and seeds.
 
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As already mentioned above, it is possible to treat all plants and their parts according to the 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
5 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 parts" his 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
10 plants having new properties ("traits") and which have been Obtained by conventional breeding; by mutageriesis or by ..recombinant DNA' techniques. They cari!be cultivars, varieties, bio- Or genotypes.
Depending on the plant species or plant cultivars, their location and growth conditions (soils,
climate, vegetation period, diet), the treatment according to The invention may also result in
15 superadditive ("synergistic") effects. Thus, for example, reduced apPlidatiOn :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 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
20 yields, better quality and/or a higher nutritional value of the harvested products, better stoinge stability and/or processability of the harvested products are possible- which exceed the effects which were actually to be expected.
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:
25 mOdification,reCeiVed genetic material which imparted particularly advantageous useful properties ftraits").6 these plants. Examples of such properties are:better plant growth, increased tolerance to high or low 'temperatures, increased tolerance to drought or 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 harveited products,' better storage. stability
j0: 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,.
 
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potatoes, cotton, tobacco, 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, tobacco and oilseed rape. Traits that are particularly emphasized are increased defence of the plants against insects, arachnids, nematodes and slugs and snails by toxins formed in the plantS, in particular
5 those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CryIA(b), CryIA(c), CryHA, CrylA, Cry111B2, Cry9c, Cry2Ab, Cry3Bb and CrilF and also combinations thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasized are the increased defence of the plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and
10 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 imidazolinoties, sulphohylureas, glyphosate or phosphinotricin (for example the 'PAT" gene). The genes which impart the desired traits in question can also be present in combinatien with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize.
15 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 NewLeafle.. (potat6). Examples of herbiCide-tolerant plants which maybe mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names koUndup Ready® •
20 (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and iSTS®, (tolerance to sulphonylureas, for exampl• maize). Herbicide-resistant plants (plants bred in a conventional manner for:herbicide tolerance) which may be mentioned also include the varieties sold under the name Clearfl eld® (for example maize). Of. course, these statements, also ap.ply.tO
25 plant cultivars which have these genetic traits or genetic traits still to be developed, and which will be developed andior Marketed in the fUtute.:
The plants listed can be treated according to the inventfoil a" particularly adVantigetitis manner
.    .    .    .    .
with the active compound mixtures according to' the invention; The preferred ranges *mid abOve
for the active. compounds or mixtures also apply to - the treatment of these plants:    •
30 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 ...stoiage area
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
I.JLV formulations.
These formulations are produced in a known manner, for example by mixing the active compounds
or active compound combinations with extenders, that is _liquid solvents, liquefied gases under
pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or
dispersants, and/or foam formers. 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 halogenated hydrocarbons, or else butane, propane, nitrogen and
20 carbon dioxide. Suitable solid carriers 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

25    material Mich as sawdust, coconut shell% ;maize: cobs and tobaeco stalks. Suitable emulsifiers
and/or foam. formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene
fatty :acid esters, polYoxyethylene-fattYaloohol ethers, for example alkylaryl polyglycol ethers,
•    -
allcylsulphonates, alkyl sulphates, .arYlsulphonates, or • else protein hydrolysates. Suitable
.    ,    .
dispersants are: for example lignoiulPhite Waste.licluora and methvlcellulose.. .    .
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 cephalinc and lecitilinc and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.
 
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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 develoOment 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, thiabendazale,.thiophanate-methyl, zoxamide
3. Inhibitors of the respiratory chain
3.1-6iinplex
20 diflumetorim 3.2 Complei L boscalid, carboxin, fenfuram, iflutolanil, furametpyr, mepronil, oxycarboxin, penthiopyrad,
thifluzamide
 
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3.3 Complex III
azoxystrobin, cyaiofamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin. kresoxim-methyl; metominostnibin, orysastrobin, pyraclostrobin, picoxystrobin
3.4 Decouplers
5 dinocap, fluazinam
3.5 ATP production inhibitors
fenthi aoetate, fentin chloride, fentin hydroxide, silthiofam
4.    Amino acid and protein biosynthesis inhibitors
andoprim, blasticidin-S, cyprodinil, kasugamycin; kasugamycin hydrochloride. hydrate, mepanipyrim, . 10 pytimethanil
5.    Signal transduction inhibitori
fenpiclonil, fludioxonil, quinoxyfen
6.    Lipid and membrane synthesis inhibitors
chlozolinate, iprodione, procymidone, vinclozolin
•15 :pyrazoPhOs,.edifenplioi, iProbnfOrs (IP), iabprothiolane tolclotoi-methyl,biphenyl
iodocarb, propamocarb,Propamocarb hydrochloride
7.    Inhibitors ofergosterol biosyntheSis,:.
fenhexainid, •
20 azaconazole, bitertanol, bromuconazole, cyproconazole, dialobutrazole, difenoconazole, diniconazole, diniconazole-M, •epoxiconazole, etaconazole, fenbuconazole, fluquinConazole,
 
- 14 -
flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, voriconatiole, imazalil, iinazalil sulphate, oxpoconazole, fenarimol, flurprimidOl, nuarimol, pyrifetiox,
5    triforine, pefurazoate, prochloraz, triflumizole, viniconazole,
aldimorph, dodemorph, dodemorph acetate,' fenpropimorph, tridemorph, fenpropidin, spiroxamine, naftifine, pyributicarb, terbinafm,.
8.    Cell wall synthesis inhibitori
benthiaValicarb, bialaphoS;dimethomorph, flumorph, iprovalicarb, polyoxins,polyoxorim, 10 validamycin
9.    Melanin blOsynthesis inhibitors
capropamid, diclOcymet, fenoxanil, phthalide, pyroquilon, tricyclazole
10.    Resistance inductors
acibenzolar-S-methyl, probenazole, tiadinil
15    11. Compoands with multisite activity
captefol, captan, chlorothalonil, copper salts, such as: copper hydroxide, copper naphthenate, copper
oXychloride,:.:Coppot. sulphate, copper oxide, Okine :copper and Bordeaux 'Mixture; dichlofluatiid,
dithiancin,--.    dodine fred baae, fethem,' fluorofolpet, folpet, fosetyl-Al, guazatine, guazatine
acetate, iniinoctailine; iinincetadine amesilate,'iminoctadine triacetate, mancopper, inancozeb; inaneb,
    _    .
20 metiram; nietiranizinc, propineh, sulphur and sulphur preparations comprising- calcium polysulphide,
tbirain,tolylfhianid, zineb, ziram
12: Unki6ivn. •
ainibromdol, benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, chlompicrin, cufraneb, .cyaufenatriid, cymoxanil, daz,oniet, debitcarb, diclomezine, dichlorophen, dicloran, difenzoqiiat,
25 difenzoquat niethylsulphate, diphenylamine, ethaboxani, ferimzone, flumetover, flusulfamide, . fluopicolide, fluoroimide, hexachlorobenzene, 8-hydroxyquinoline sulphate, irumamycin,
 
- 15 -
methasulfocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel
dimethyldithiocarbamate,    nitrothal-isopropyl,    octhil inane,    oxamocarb,    oxyfenthiin,
pentachlorophenol and salts,2-phenylphenol and salts, piperalin, prOpanosine—sodium, proquinazid,
pyrrolnitrin, quintozene, tecloftalarif, tecnazene, triazoxide, trichlamid, zarilamid and 2,3,5,6; •
tetrachloro-4-(methylSulphonyl)pyridine,    . N-(4-chloror2-nitrophenyl)-N-ethy1-4-
methylbentenesulphonamide, 2-amine-4-methyl-N-phenyl-5-thiazolecarboxamide, 2-chloro-N-(2,3-
dihydro-1,1,3-trimethy1-114-inden-4--y1)-3-pyridinecarbexamide,    . 345-(4-ehloroPheny1)-2,3-
dhnethylisoxazolidin-3-yl]pyridine,    cis-1 -(4-ch loropheny1)-27( 1147 1,2,4-triazol-1-ypeyelotieptinol,
2,4-dihydro-5-methoxy-2-methyl-4-Ea1-[3-    S
.10    (trifluaroinethyl)phenYl]ethylidenejaniino]oxy]methyl]pheny1]-31-1-1,2,3-iriazol-3-one (135336-79-2),
. methyl 142,3 -dihydro-2,2-dimetbyl-1H-inden-144)-1I-1-imidazole-5-carbOxYlate: 3,4,5-triehioro-2,0-.
pyridinedicarboriltrile, methyl , 2-[[[CycicipropylT[(47methoxyphenyl)iminO]methyljthiirjrnethylj-a-.
(Methoxymethylene)benzyl    • acetate,    4-chlono-a.-propYttyloxy-N-(2437methoxy-4-(2-
propynyloxy)phenyl]ethyl]benzacetarnide,    (2S)-1,14244-[[3-(4-chlOropheriy1)-2-propynyl]oxy]-3.- •
15    methoxyphenyllethy1]-3-rnethy172-[(methylstrIPhOtiOamino]butanaMide,    5-chlorO-7-(4-. •
methylpiperidin- 1 -y1)-6-(2,4,6-iiifl uorophenY1)[1 72,4]triazolo [ 5-chloro-6-(2,4,6- trifluorepheny1)-N-R iR)-1,2,2-trinnethylpropYlj[1,2,4]triazolo[1,5-a]Pyrimidin-77amine,.5-chlor044- [(1R)-1,2-dimethylprOpy1]-6-(2,4,0-trilluorophenkl,2,4]triazolo[1,5-a]pyrimidin-7-ainine, .1441-(5- bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicatinamide, N-(5-bromo-3-chloropyridin-2-
20 y1)methy1-2;4-dichloronicotinamide,    2-butoxy-6-iodo-3-propylbenzopyranon-4-one,    N-{(Z)-
[(cyclopropylmethoxy)imino][6-(difluoromethOky)-2,3-diflubrophenyl]methyl)-2,benzacetainide;    .
(3-ethy1-3,5,5-trimethylcyclohexyl)-3-formYlarnino-2-bydrOXybenzamide,    2-4[113,-(1...fluoro-27.
phenylethyl)oxy]phenyljethylidene]amincloxy]methyl]-a-(methoxyimino)-N-methYl-o..Ez berizacetamide, N-{2-[3-chloro75,-(trifluoromethyl)pyridin-2-yi]ethyl}-2-(trifluoremethy1)benzamide,
25 ..N-(31,*-dichloro-5-ibiorobipheny1-21)-3-(difiriorometbyl),1-itetbyl-lH-PyrazOle4-cricamicle,* (64iiethOXy-3Lpyridinyi)cyCioPrOPaireOartrOrearnitle,".    "     • .14(4ineilio    tir 1] *2 2
           • xYP enoxY    Y -
.    .    • 
dirnethylpropylL11:1-imidaZoleearboXylic    -[(4-nrethOrrYPherroxyjmethY1]-2,2-
diniethylpropY1]-1H-imidazble:1-car bothieic    acid, - 2-(2([6-(3-1ileirc-2-inetbYlphentucy)-5-'
flUiropyriinidin-4-yl]oxy}PhenYlj.-2-(rnethoxy iinina)-bl-inethYlacetamicie
30 Bactericides:
bronopol; dichlorophen, nitraPyrin, • nickel dimethyldithiecarbamate,-    'octhilinone,
furancarhoxylic acid, oxytetracyclin, probenazole; streptomycin, tecloftalam, copper :sulphate and other copper preparations.
 
Insecticides / acaricides / nematicides:
1.    Acetylcholinesterose (ACNE) 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 brotnophos-ethyl, - bromfenvinfos (-methyl), :butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenv.inphos; chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-s-methyl, demeton-s-methylsulphon,.dialifos, diazinon, diehlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion,
15 fensulfothion, fenthion, flupyrazofos, fonofos, fonnothion, fosmethilan, fosthiazate, heptenophos, iodbfenphok, iprobenfos, isazofos, isofenphos, isopropyl o-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxyderneton-methyl, parathion (-methyl/-ethyl), phenthoate, phorate, phosalone, phosinet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos,
20 prOpaPhos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, . quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thioineton, triazophos, triclorfon, vainidoth idn)
2.    Sodium channe1modulatorS(bloCkers of voltage-gate-4 sodium channels
2.1 pyrethrciids (for example'acrinithrin, allethrin (d-cis-trans, l-trans), betacyfluthrin, bifenthrin,
25 bioallethrin, bioallethrin-g-cyclopentyl-isoiner; bioethanomethrin, bioperinethrin, .bioresmethrin; chlovapOrthrin, cis-cypermethrin, cis7resmethrin, cis-permethrin, clocythrin, cycloproflirin,IcyfluT thrin, .eyhalothrin, cypermethrin: (alpha-, 'beta-, theta--, zeta-), cyphenothrin, DDT, deltimethrin; empenthrin (1R-isomer), .esfenValerate, .etofenpt.„ fenfluthrin, fenpropathrin, fenpyrithrin, fen= . valerate; fltibrocythrinate, flUeythrinate, flutenprox,: flutheihrin, fluValinate, fubfenprox, gamnia,
30 cyhalothrin,- imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-); phenothrin (1R-trana isomer), pmllethrin,' profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate,- tefluthrin, terallethrin, tetramethrin (1R-isomer), tralomethrin, transfluthrin, ZX1 8901, vvrethrins (ovreiluannll
 
- 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 mimetics
(for example diofenolan, epofenonane, fenpxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, tripiene)
.8...Ecdyson agonistedisruptors
• 8.1 diacylhydrazines (for example .chroinafencizide, halofenozide, methoxyfenozide, tebufenoiide) 20 ' 9. Chitin biosynthesis inhibitors
9.1 benzoylureas (for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuroa,- flufenoxuron, hexaflumuroir,' lufenuron, novaluron, noviflumuron, penfhiron, teflubenzuron, triflumuron)
9:2 buprofezin 25 9.3 cyromazine
 
-18-
10.  Inhibitors of oxidative phosphotylation, 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 '11.1 pyrroles (for example chlorfenapyr)
11.2 dinitrophenols (for example binapacryl, dinobuton,dinocap, DNOC)
12.    Site-1 electron transport inhibitors
12.1 METIs (for example fenazaouin_ :fenpyroximate, pyrimidifen, pyridaben, tebtifenpyrad, tOlfeOpyrad)
10    12.2 hydramethymone
12.3 dicdol
13.    Site-II electron transport inhibitors
13.1 rotenone
14.    Site-III electron. transport inhibitor's
15    14.1 a.cequinocyl, fluacrypyrim
15.Nicrobial disruptors; of the insect.gig membrane taeillui.thuringieuSii strains
16..Inhibitors of fat synthesis -
16.1.letronic acidS (for example spirodiclofen, spiromesifen)
20    162 tetramic acids [for example 3-(2,5-iiimethylpheny1)-8-methoxy-2-oxo-1-azaspiro[4.5]cleo73-
: ethyl carbonate (alias: • caibonie:. acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo=1-azaspiro[4.5]dec-3-en-4-y1 ethyl ester, CAS Reg. No.: 382608-10-8) and carbonic acid, cis-3-.(2,5- dimethylphenyl):8-methoxy-2-bxo-1-avaspirO[4.5]dec-I-en-4-y1 ethyl ester (CAS Reg. No.: 203313-25-1)]
 
.19-
17.    Carboxamid es
(for example flonicamid)
18.    Octopaminergic' aRonists
(for example amitraz)
5 19. Inhibitors of magnesium-stimulated ArPase
(for 'example Propargite).
20.    Phthalatindes
(for;example    N2-[1,1-dimethy1-2-(methylsulphonyl)ethyl]-3-iodo-N42-methyl-441,2,2,2-
tetraflooro-1-(trifluoroinethypethYl]phenyl]1,2-benzenedicarboxamide (CAS Reg. No.: 272451- ] 0 .65-7), flubendiamide).
21.    Nereistoxin analogues
(for example thioeyclain hydrogen oxalate, thiosultap-sodium)
22.    Biologicals, hormones or pheromones
(for example azadirachtin, Bacillus spec., Beauveria spec., Codlemone,' Metarrhizi rn spec.; 15    Paecilomyces spec., Thuringiensin,Verticillinin spec)
23.    Active compounds with unknown or unspecific mechanisms of action
234funiigants (for example aluminium phosPhide, methyl hrOmide, sulphuryl fluoride) 23.2 selective antifeedints'(for example cryblite,-flonicamid, pymetrOzini).
233 Mite. growthinhibitors (for example Clofentezine, etoxazole, hexythiazox)
20 23A dinicioflumet benclothiaz, benzoximate; bifenazate; biontopropylate,'buprofeziti, chinoniethi7 ,•    ... •    .
Onat,    chlorobenzilate,.chloropicrin, clothiazoben, cycloprene, cyflumetofen, di-
.. cyclanil, • fenoxicrim; fennifanil, flubenziinine, flufenerim, flutenzin,•-• gOisyplure, hydramethyl-' • none, jaPOniluse,metoxadiazone, petroleum, piperonyl butOxide, potassium oleate, pyrafluprole, pyridalyl, pyriprole, sulfluramid, tetradifon, tetrasul, triarathene, verbutin,
25 furthermore the compound 3-methylphenyl propylcarbamate (Tsnmacide Z), the compound 3-(5-chloro¬3-pyridiny1)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane-3-carbonitrile (CAS Reg. No. 185982-80-
 
- 20 -
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, or with fertilizers and growth
    - 5    regulators, safeners and/or semiochemicals 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 formniatiOns'or the
 10 use forms prepared . therefrein,• such as ready-to-use . sOlutions, emulsifiable concentrates, emulsions, susPensiOns, wettable powders; soluble powders and grannies. 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 activecomponnd 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 g,/ha. For seed dressing, the active-compound combination applicaticin rates are generally between 0.001 and 50 g per kilogram:of seed, preferably between 0.01 and 10 g per kilogjain of seed. For the treatment of the soil, die
20 active-compound cOmbination: application rates " are generally between 0.1 and 10 000 g/ha, preferably between land 5 000 Wha.
ThO good fungicidal activity of the active-compound combinations according to the invention' is
denionstrated    the, eXimples beloW, Whereas .the" individual active • cOMponndS '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 thin the sum of the actiirities_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 Reslionses of Herbicide Combinations"; Weeds 15 (1967), 20-22) as follows:
 
- 21 -
If
X    denotes the efficacy when using active compound A at an application rate of m gfha,
Y    denotes the efficacy when using active compound B at an application rate of na, and
E    denotes the efficacy when using active compounds A and B at application rates of m and n
g/ha,
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.
 
- 22 -
Example
Leptosphaeria nodorum test (wheat) I protective
Solvent:    50 parts by weight of N,N-dimethylacetamide
EmUlsifier:    1 part by weight of alkylaryl polyglycol ether
To prepare 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 coMbintion with water is diluted with water to the desired • concentration.
10 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 sprayed with a spore•suspension of Leptosphaeria nodorum. The plants remain in an incubation cabin at 20°C and 100 % relative atmospheric humidity for 48 hours.
The plants are placed in a greenhouse at a temperature of about 20°C and a relative atmospheric 15 huMidity of 80 %.
Evaluation is carried out 10 days after inoculation. Here, 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
The good fungicidal activity of the preferred active compound combination is evident from the example below, whereas the other active compound combinations have weaknesses in their • 20    fungicidal activity. The activity also exceeds a simple addition of activities.
'The table beloi.V sholks clearly thalthe activity found for the active compound` combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present. The.synergism found is surprisingly clearly pronounced for the mixing ratios accoraii;ito the invention, the mixing ratio according to the invention of 1:15 having the most pronounced
25    Synergistic effect.
 
- 23 -
Table
Leptosphaeria oodorum test (wheat) / protective
Active Known:        compound    Active compound application rate in PPni    % efficacy
               
Trifloxystrobin
.    Ol    ",.. ,.0
N    N1161
•    25    50
F    F
F               
Captan
•    O    —s
a
et
ci    500
375
82.5
-    25
25
50

Mixture according to the invention:
Mixing ratio    Active    Actual efficacy Expected value
CoMpoUnd    calculated using
 Colby's formula application
Tate in pprin

Trifloxystrobin    1:20
' -"-
Copt=    25
500        75   
Trifloxystrobin    )    1:11*    - 25            63
+       -:4-..           
Captan    :375.           
Trifloxystrobin    1:3.3    .25    }    50    75
+    +           
Captan    82.5           
* a mixing ratio according to the invention               
 
-24-
Patent claims
1.    Active compound combination comprising a compound of the formula (I)
 

 
and
5    (2)    a compound of the formula (11)
 
N—S\
CCI,    (II)
(captan).
 
    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 1:10 to 1:19.
    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 fOrtnula (11 to active compound of the formula MI is from 1: 12 to 1:18.
4.    Active compoimd 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 forinula (II) is from 1: 14 to 1:16.
5.    Method foi-controlling phytOliathogenic fungi, characterized in that an active compound • combination according to any 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.
 
-25-
6.    Method according to Claim 5, characterized in that the compound (I) according to Claim I and the compound (II) 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 mare of Claims I 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.
 

In I &min I ownru. ounnvn nmr-vn 1    International application No
PCT/EP2006/011605
A.    CLASSIFICATION Of SUBJECT MATTER
INV.    A01N37/50    A011,147/04    AO1P3/00
According to International Patent Classification (PC) or to both national classification and IPC
B.    FIELDS SEARCHED
Minimum documentation searched (classification syetem followed by classification symbols)
AO1N
' Documentation searched other than minimum documentation to tiro extant that such documents are included in the flelde searched
Eledronlc data base consulted during the international search (name of data bane end, wham practical, search terms used)
EPO -Internal, WPI Data
C.    DOCUMENTS CONSIDERED TO BE RELEVANT
Category'    Citation of document, with indication, where appropriate, of the relevant passages    Relevant to claim No.
A
A    WO 97/06684 A (BASF AG [DE]; SCHWALGE BARBARA [DE]; MUELLER RUTH [DE]; BAYER HERBERT) 27 February 1997 (1997-02-27) page 1, lines 6-39
Tables on pages 7-8
----
WO 95/35033 A (BASF AG [DE]; AMMERMANN EBERHARD [DE]; LORENZ GISELA [DE]; MAPPES DIET) 28 December 1995 (1995-12-28)
page 1, lines 6-39
page 6
----    1-10
1-10
X    Further documents are listed in the continuation of Box C.    X    See patent family annex.
•    Special categories of cited documents r
T tater document publshed after the international fling date or windy date and not in conflict with the applIcatbn but
'A' document darning the general slate of the art Mtn Is not    cited to understand the prIndple or theory underlying the
considered to be of particular relevance    Invention
'E' earlier document but publiehed on or after the InternaiMnal
filing date    "X' document of particular relevance; the claimed Invention
cannot be considered novel or cannot be considered to
V document Which rosy throw doubts on priority claim(s) or    involve an Inventive step when the document is taken alone
which is cited to.b.. lish the publication date of another    y    document of particular relevance; the oleimed invention
chadon or other special reason (es specified)    cannot be considered to involve an inventive step when the
'0' document referring to an oral dIsdosure, use, exhihnion or    document Is combined with one or more other such docu-
other means    mente, suds combination being obvious to a person ?Wiled
•    P• document published prior to the international fiting date but    in the art.
later then the priority date claimed    'V document member of the same patent family
Date of the actual completion of the international search
22 March 2007    Date of mailing of the international seeroh report
04/04/2007
Name and mailing address of the ISN
European Patent Office, P.B. 5818 Petermann 2 NI - 2280 HV Filswp
TeL (+01-70) 340-2340, Tx. 31 051 epo ni, Fax: (+31-70) 340-3018    Authorized officer
Klaver, Jos

Form POT/I9A/210 (second sheet) (epd12005)
page 1 of 2
 

IN I &nlIF1/4 I IUNAL bLARUI-1 litrUli 1    International application No
PCT/EP2006/011605
C(ContinuatIon).    DOCUMENTS CONSIDERED TO BE RELEVANT
Category*    Citation of document, with Indication where appropriate, of the relevant paean.    Relevant to claim Na
A
A    ANONYMOUS:    "Fungicidal compositions"
RESEARCH DISCLOSURE, MASON PUBLICATIONS, HAMPSHIRE, GB,
vol. 415, no. 12, November 1998 (1998-11), pages 1437-1439, XP007123477
ISSN: 0374-4353
cited in the application
the whole document
-----
WO 97/00012 A (CIBA GEIGY AG [CH]; KNAUF BEITER GERTRUDE [DE]; KUENG RUTH BEATRICE [C) 3 January 1997 (1997-01-03)
cited in the application
page 1, paragraph 2 - page 3, paragraph 1 page 6, paragraph 6; examples
B2,B4,B6,B8,B11
-----    1-10
1-10
Foan POT/WEI° (continuation of second 'sheet) (April 2005)
page 2 of 2
 
ntsTERNATIONAL SEARCH REPORT
itiltenotion of poke& Imllyr rimibots       
    natkriPI Iftplipadua
PCTIEpzOOknimos
Patent docurrerit
cited In cearEti repot        PoNicat on
date        AM. lardy inambar(s)    Pula t Edon
d21
140 9706664    A    27-02-1997    AT    185679 T    15-11-1999
            AU    6742296 A    12-03-1997
            BR    9610004 A    06-07-1999
            E1'    0844822 Al    -    03-06-1998
            OP    3883576 82    21-02-2007
            JP    11511150 T    28-09-1999
            US    5965599 A    12-10-1999
            Irk    9606961 A    16-02-199#
Wo 9625033    A    28-12-1995    AT    16521.0 T    15-05-1998
            AU    692273 52    04-06-1998
            AU    2768996 A    15-01-199
            BS    63185 B1    29-06-2001
            in    101054 A    30-04-1998
            OR    9508056 A    12-08-1997
            CA    2193128 Al    28-12-1995
            CZ    9603688 A3    16-04-1997
            OE    4471041 Al    21-12-1995
            0k.    765118 T3    07-10-1998
            EP    0765118 Al    02-04-1997
            ES    2115385 T3    16-06-1998
            HIi    75946 A2    30-'06-1997
            IL    114126 A    28-09-2900
            OP    10502909 1'    17-03-1998
            NZ    288602 A    27-05-1998
            PL    317832 Al    28-94-1997
            RU    2152720 01    20-07-2000
            8K    162196 A3    10-09-1997
            US    6877201 A    02-03-1999
            ZA    9504971 A    17-12-1996
140 9700012    A    03-01-1997    AR    002477 Al    25-03-1998
            AT    20006 7    15-10-2001
            AU    690464 82    23-04-1998
            AU    6225196 A    15-01-1997
            BR    9608358 A    18-09-11)98
            CA    2224977 Al    03-01-1997
            CN    1636455 A    23-07-2006
            CZ    9704040 A3    13-05-1998
            DE    69515552 Dl    31-10-2001
            DE    69615552 T2    18-04-2002
            OK    831698 T3    21-01-2002
            EA    525 91    28-10-1999
            EP    0831698 Al    01-04-1998
            ES    2164248 T3    16-02-2002
            HU    9802198 A2    28-01-1999
            IL    122317 A    23-12-2001
            JP    116076E5 T    08-07-1999
            NZ    310452 A    29-09-109
            PI_    323945 Al    27-04-1998
            PT    831698 T    28-0-2007
            TR    9701619 11    21-05-1998
            US    5998435 A    07-12-1999
            ZA    9605080 A    17-12-1996

frrn, pc-tgautro raw family init..) 6.4
 
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