ZA200603200B - Fungicidal mixtures for fighting against rice pathogens - Google Patents

Description

PF 254900 ® 1 - 29086703200

Fun gicidal mixtures for fighting against rice pathogens

The present invention relates to fungicidal mixtures for controlling ricce pathogens, which mixtures comprise, as active components, 1) the triazolopyrimidine derivative of the formula |,

CH,

CO)

N F

CATS

NEN a © and 2) a phthalimide derivative Il selected from the group consisting of a) captan of the formula lia,

O

CI rs lla oO and b) folpet of the formula lb,

Oo

CI se Hib (© J in a synergistically effective amount.

Moreover, the invention relates to a nethod for controlling rice pathogens using mix- ture=s of the compound | with the compounds Il and to the use of the compound I with the compounds I for preparing such rmixtures and compositions conprising these mix- ture=s.

The- compound |, 5-chloro-7-(4-methy Ipiperidin-1-yl)-6-(2,4,8-trifluorcophenyl)(1,2,4]tri- azo Yo[1,5-a]pyrimidine, its preparation and its action against harmful fungi are known fron the literature (WO 98/46607).

"PF 54900

The phthal imide derivatives lI, 2-trichloromethryisuifanyl-3a,4,7,7a-tetrahydr-oisoindole- 1,3-dione (lla; common name: captan) and 2-®richloromethylsulfanylisoindo=le-1,3-dione (lib; comm on name: folpet), their preparation aand their action against harm®ut fungi are liekwise krmown from the literature (US 2 553 770; US 2 553 771, US 2 553 776). The phthalimides derivatives Il have been commercially established for a long tire as fungi- cides, mairly against Oomycetes.

Mixtures off triazolopyrimidine derivatives with captan are proposed in a gereral man- ner in EP-A 988 790. The compound | is embmraced by the general disclosu sre of this publication, but not explicitly mentioned. Acco rdingly, the combination of cosmpound with captar is novel. Folpet is not mentioned i n EP-A 988 790.

The synergistic mixtures known from EP-A 98:8 790 are described as beings fungicidally active agamnst various diseases of cereals, fru it and vegetable, for example mildew on wheat and barley or gray mold on apples.

However, the fungicidal action of the known mixtures is not always entirely satisfactory.

A need exi sts to provide, with a view to an effective control of rice pathogers at appli cation rate=s which are as low as possible, mix-tures which, at a reduced totaal amount of active comm pounds applied, have an improved effect against the rice pathoggens.

Owing to the special cultivation conditions of rice plants, the requirements t hat a rice fungicide mas to meet are considerably differe nt from those that fungicides wused in cereal or fruit growing have to meet. There are differences in the applicatiomn method: in addition to the much-used foliar application in modem rice cultivation the fue ngicide is usually applied directly onto the soil during or shortly after sowing. The fungicide is taken up ireto the plant via the roots and transgoorted in the sap of the plant ®o the plant parts to be protected. in contrast, in cereal or fruit growing, the fungicide is usually ap- plied onto ®he leaves or the fruits; accordingly, in these crops the systemic aaction of the active com» pounds is considerably less importaant.

Moreover, rice pathogens are typically differert from those in cereals or frust. Pyricu- lana oryzaee and Corticium sasakii (syn. Rhizo~ctonia solani) are the pathogens of the most significant diseases in rice plants. Rhizoectonia solani is the only pathcgen of agri- cultural sign nificance from the subclass Agariccomycetidae. This fungus attacks the plant not via spares like most other fungi but via a nnycelium infection. 40

AMIENDEDs SHEXET

"PF 5.4900

For thhese reasons, findings concerning the fungicidal action in the cultivaticon of cereals or frumit cannot be transferred to rice crops.

Practical agricultural experience has shown that the repeated and exclusivee application of an individual active compound in the co mtrol of harmful fungi leads in maany cases to the rapid selection of fungus strains which have developed natural or adapted resis- tance2 against the active compound in quesstion. Effective control of these fungi with the active2 compound in question is then no lormger possible.

To readuce the risk of selection of resistant fungus strains, mixtures of differ-ent active compounds are nowadays preferably emp loyed for controlling harmful funggi. By com- bininag active compounds having different rmechanisms of action, it is possitole to ensure a suczcessful control over a relatively long goeriod of time.

A nee=d exists to provide, with a view to effective resistance management a nd an effec- tive control of rice pathogens at applicatior rates which are as low as possible, mix- tures which, at a reduced total amount of active compounds applied, have san improved effect against the harmful fungi.

We hmave found that this need is fulfilled by the mixtures defined at the outs et. Surpris- ingly, it has been found that the mixtures aaccording to the invention of the t ria- zolopmyrimidine derivative | with the phthalirnide derivatives Il are considerably more active= against pice pathogens than the mixtures, proposed in EP-A 988 79€, of the structurally similar triazolopyrimidines A or B with captan.

CH, ® LF

F

N H.C" "NH F

NN A NN“ B ¢ ¢ _ =

N=? a © N=? cl

More over, we have found that simuitaneotis, that is joint or separate, appliccation of the compound | and one of the compounds Il Cr successive application of the czompounds and one of the compounds |] allows better control of rice-pathogenic harmful fungi than is posssible with the individual compounds.

Wher preparing the mixtures, it is preferre d to employ the pure active compounds | and lta or lib, to which further active compounds against harmful fungi or other pests, such

AMENDED SHEET

PF 54900 as insects, arachnids or nematodes, or else he=rbicidal or growth-regulatingg active com- pounds or fertilizers can be added as required .

Other suita ble fungicides in the above sense are in particular fungicides selected from the followin g group: e acylalamines, such as benalaxyl, metalaxyll, ofurace or oxadixyl, e amine derivatives, such as aldimorph, dod emorph, fenpropimorph, fen propidin, guazatime, iminoctadine, spiroxamine or tri demorph, eo anilinopyrimidines, such as pyrimethanil, nmepanipyrim or cyprodinyl, e antibiotics, such as cycloheximide, griseofulvin, kasugamycin, natamyezin, polyoxin or strepstomycin, e azoles, such as bitertanol, bromoconazole , cyproconazole, difenoconzmzole, dinitro- conazolle, enilconazole, epoxiconazole, ferbuconazole, fluguinconazolle, flusilazole, flutriafo 1, hexaconazole, imazalil, ipconazo le, metconazole, myciobutaril, pencona- zole, pr opiconazole, prochloraz, prothiocorazole, simeconazole, tebuconazole, tet- racona=ole, triadimefon, triadimenol, triflurmizole or triticonazole, o dicarbo ximides, such as iprodione, mycloz olin, procymidone or vincloz=olin, « dithiocaarbamates, such as ferbam, nabam , maneb, mancozeb, metam , metiram, propine b, polycarbamate, thiram, ziram or zineb, e heteroc=yclic compounds, such as anilazine, benomyl, boscalid, carbermdazim, car- boxin, ©xycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fen=amidone, fenarim ol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil,, nuarimol, picoberizamid, probenazole, proquinazid, goyrifenox, pyroquilon, quino>=yfen, silthio- fam, thi abendazole, thifluzamide, thiophan ate-methyl, tiadinil, tricyclaz-ole or tri- forine, e copper fungicides, such as Bordeaux mixture, copper acetate, copper oxychloride or basic copper sulfate, e nitrophenyl derivatives, such as binapacryll, dinocap, dinobuton or nitrcphthal- isoprop Yi, e phenylpyrroles, such as fenpiclonil or fludicoxonil, e sulfur, « other fuangicides, such as acibenzolar-S-meethyl, benthiavalicarb, carprepamid, chlorothalonil, cyflufenamid, cymoxanil, diclomezine, diclocymet, dietheofencarb, edifenp hos, ethaboxam, fenhexamid, fentim-acetate, fenoxanil, ferimzamne, fluazinamm, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafe=none, pencycuron, propamocarb, [ohthalide, tolclofos-methy!, q uintozene or zoxamicie, e strobiluwrins, such as azoxystrobin, dimoxysstrobin, fluoxastrobin, kresoxxim-methyl, 40 metomi nostrobin, orysastrobin, picoxystrotoin, pyraclostrobin or trifloxysstrobin,

PF 54900 ® 5 e sulfenic acid derivatives, such as captafol, dichlofluanid or tolwylfluanid, e cinnamides and analog ous compounds, such as dimethomorpoh, flumetover or flu- morph.

In one embodiment of the mixtures according to the invention, a f urther fungicide Ill or two fungicides Ill and 1V are added to the compounds | and Il.

Preference is given to mixtures of the compounds | and Il with a ccomponent Ill. Particu- lar preference is given to mixtures of the compounds | and lla or | 1b.

The mixtures of the compounds | and Il, or the compounds | and &he compound Il used simultaneously, that is jointly or separately, exhibit outstanding action against rice pathogens from the class of the Ascomycetes, Deuteromycetes a nd Basidiomycetes.

They can be used for the treatment of seed as well as as foliar- a nd soil-acting fungi- cides.

They are especially important for controlling harmful fungi on rice plants and their seeds, such as Bipolaris ard Drechslera species and Pyricularia =oryzae. They are par- ticularly suitable for controlling rice blast caused by Pyricularia ormy/zae.

Moreover, the combination of compounds | and Hl according to the invention is also suitable for controlling other pathogens, such as Septoria and Pueccinia species in ce- reals and Alternaria and Botrytis species in fruit, vegetables and grapevines, for exam- ple.

They can also be used in the protection of materials (e.g. the prot-ection of wood), for example against Paecilomy/ces variotii.

The compound | and the compound lla or lib can be applied simumlitaneously, that is jointly or separately, or in succession, the sequence, in the case Of separate applica- tion, generally not having a ny effect on the result of the control me=asures.

The compound | and the compounds lla and IIb are usually applied in a weight ratio of from 100:1 to 1:100, preferably from 10:1 to 1:50, in particular fromm 5:1 to 1:20.

Depending on the type of compound and the desired effect, the a pplication rates of the mixtures according to the invention are from 5 g/ha to 2000 g/ha, preferably from 50 to 1500 g/ha, in particular frorm 50 to 1000 g/ha.

PF 54900 ® 6

Correspomdingly, the application rates of the compound | are generally frorm 1 to 1500 g/ha , preferably from 10 to 1200 g/ha, in particular from 20 to 900 kg/ha.

Correspormdingly, the application rates of the compound lla or lib are generally from 1 to 2000 g/ ha, preferably from 10 to 1500 g/ha, in particular from 20 to 1000 g/ha.

In the trea tment of seed, the application rates of the mixture are generally from 1 to 1000 g/10 Okg of seed, preferably from 1 to 2040 g/100 kg, in particular frorm 5 to 100 9/100 kg.

In the control of harmful fungi which are pathogenic for rice plants, the sep arate or joint applicatiom of the compounds | and the compomund lla or lib or of the mixtumres of the compound | and the compound lla or |Ib is carried out by spraying or dustimng the seeds, the seedlings, the plants or the soils before or after sowing of the pRants or be- 16 fore or after emergence of the plants. The appl ication of the compounds preferably takes place jointly or separately by spraying thee leaves. The application of the com- pounds can also take place by applying granules or by dusting the soil.

The mixtu res according to the invention or the compounds | and Il can be «onverted into the clListomary formulations, for example seolutions, emulsions, suspen sions, dusts, powders, gpastes and granules. The applicatiorm form depends on the particular pur- pose; in each case, it should ensure a fine andl uniform distribution of the compound according to the invention.

The formulations are prepared in a known mariner, for example by extendi ng the active compound with solvents and/or carriers, if desi red using emulsifiers and di spersants.

Solvents/auxiliaries which are suitable are essentially: - wanter, aromatic solvents (for example SSolvesso products, xylene), paraffins (for example mineral fractions), alcohols (foar example methanol, butanol, pentanol, be nzyl alcohol), ketones (for example c=yclohexanone, gamma-butysrolactone), py Trolidones (NMP, NOP), acetates (glw/col diacetate), glycols, fatty= acid dirmethylamides, fatty acids and fatty acid esters. In principle, solve nt mixtures may also be used, - ca rrers such as ground natural mineral s (for example kaolins, clay=s, talc, chalk) an d ground synthetic minerals (for exarmple highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (for example po lyoxyethylene fatty alcohol ethers, allkylsulfonates and arylsulfon ates) and disspersants such as lignin-sulfite waste liquors and methylcellulose=.

® 7

Suitable surfactants are alkcali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthal enesulfonic acid, phenolsulfonic ac id, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfa tes, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensatess of naphthalene or of naphthalenessulfonic acid with phenol and formaldehyde, polyoxy<ethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributy Iphenyl polyglycol ether, tristearylphenyl polyglycol esther, alkylaryl polyether alcohols, a Icohol and fatty alcohol/ethylene oxide conclensates, ethoxylated castor oil, po Tyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste | iquors and methylcellulose.

Substances which are suitable for the preparation of directly syorayable solutions, emulsions, pastes or oil dis persions are mineral oil fractions of” medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils &nd oils of vegetable or animal origin, aliphatic, cyc lic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphtha lene, alkylated naphthalenes or the ir derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isop horone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.

Powders, materials for spresading and dustable products can b < prepared by mixing or concomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds tc solid carriers. Examples of solid carriers are minerall earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole , loess, clay, dolomite, diatomaceots earth, calcium sulfate, magnesium sulfate, magne sium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium suxlfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origim, such as cereal meal, tree bark me=al, wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulationss comprise from 0.01 to 85% by weight, preferably from 0.1 to 90% by weight, of the ac tive compounds. The active compo unds are employed in a purity of from 90% to 100%, preferably 95% to 100% (accordirig to NMR spectrum).

PF 54900 ® g

The following are examples of formulations: 1. Products for dilution with wat-er

A) Water-ssoluble concentrates (SL) 10 parts by w-eight of the active compounds are cdissolved in water or in a water-soluble solvent. As ar alternative, wetters or other auxilizaries are added. The active compound dissolves uposn dilution with water.

B) Dispers ible concentrates (DC) 20 parts by weight of the active compounds are dissolved in cyclohexanone with addition of a dispersant, for example polyvinylpyr-rolidone. Dilution with wate=r gives a dispersion.

C) Emulsifiable concentrates (EC) parts by weight of the active compounds are dissolved in xylene with addition of 15 calcium dode cylbenzenesulfonate and castor oil ethoxylate (in each case 524 strength).

Dilution with water gives an emulsion.

D) Emulsions (EW, EO) 40 parts by w=eight of the active compounds are dissolved in xylene with addition of calcium dode cylbenzenesulfonate and castor oil ethoxylate (in each case 5 strength).

This mixture Es introduced into water by means o f an emulsifier (Ultraturax) sand made into a homogeneous emulsion. Dilution with watezr gives an emulsion.

E) Suspermsions (SC, OD)

In an agitatecd ball mill, 20 parts by weight of the active compounds are com minuted with addition of dispersant, wetters and water or an organic solvent to give & fine active compound staspension. Dilution with water gives a stable suspension of the active compound.

F) Water-cdispersible granules and water-soluble granules (WG, SG) 50 parts by weight of the active compounds are ground finely with addition of dispersants aand wetters and made into water-disspersible or water-soluble g ranules by means of technical appliances (for example extrusion, spray tower, fluidized bed).

Dilution with water gives a stable dispersion or s=olution of the active compound.

G) Water-cdispersible powders and water-solulble powders (WP, SP) 75 parts by weight of the active compounds are ground in a rotor-stator mill with addition of disspersant, wetters and silica gel. DilLution with water gives a stalole dispersion or solution of the active compound.

PF 54900 @® 9 2. Products to be appelied undiluted

H) Dustable powders (DP) parts by weight of the active compounds are ground fineRy and mixed intimately with 5 95% of finely divided kaolin. This gives a dustable product_ 1) Granules (GR, FG, GG, MG) 0.5 part by weight of the a <tive compounds is ground finely and associated with 95.5% carriers. Current methods are extrusion, spray-drying or th € fluidized bed. This gives granules to be applied undiluted.

J) ULV solutions (UL) 10 parts by weight of the active compounds are dissolved in an organic solvent, for example xylene. This give s a product to be applied undiluted.

The active compounds cam be used as such, in the form o¥ their formulations or the Lise forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or clispersions, emulsions, oil dispe rsions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pour-ing. The use forms depend entir-ely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active compounds according to the invention.

Aqueous use forms can bes prepared from emulsion conce nitrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or disscalved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier.

Alternatively, it is possible to prepare concentrates compos=sed of active substance, wetter, tackifier, dispersarit or emulsifier and, if appropriates, solvent or oil, and such concentrates are suitable for dilution with water.

The active compound con centrations in the ready-to-use preparations can be varied within relatively wide rang es. In general, they are from 0.02001 to 10%, preferably fro m 0.01 to 1%.

The active compounds may also be used successfully in the ultra-low-volume processs (ULV), it being possible to apply formulations comprising over 95% by weight of actiwe compound, or even to apply the active compound without additives.

PF 54900 ® 10

Various types of oils, wetters , adjuvants, herbicides, fungicides, sother pesticides, or bactericides may be added to the active compounds, if appropriate just immediately prior to use (tank mix). Theses agents are usually admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.

The compounds | and Il or th e mixtures or the corresponding formmulations are applied by treating the harmful fungi ©r the plants, seeds, soils, areas, m aterials or spaces to be kept free from them with a fungicidally effective amount of the= mixture or, in the case of separate application, of the compounds | and Ii. Applicat ion can be carried out before or after infection by th € harmful fungi.

The fungicidal action of the c ompound and the mixtures can be cdemonstrated by the experiments below:

The active compounds, sepa rately or jointly, were prepared as a stock solution with 0.25% by weight of active co mpound in acetone or DMSO. 1% bey weight of the emulsi- fier Uniperol® EL (wetting ag ent having emulsifying and dispersi ng action based on ethoxylated alkylphenols) wa s added to this solution, and the soR ution was diluted with water to the desired concentration.

Use example — protective activity against rice blast caused by Pywricularia oryzae

Leaves of rice seedlings of thes cultivar "Tai-Nong 67", which had b-een grown in pots, were sprayed to runoff point with an aqueous suspension having tie concentration of active compounds stated below. The next day, the plants were ino culated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatized chambers at 22-24C and 95-99% relative atmospheric humidity for 6 days.

The extent of the developmerut of the infection on the leaves was tken determined visually.

The visually determined value=s for the percentage of infected leaf areas were converted into efficacies as % of the untreated control:

The efficacy (E) is calculated as follows using Abbot's formula:

E=(1-a/B) 100 o corresponds to the fungicidal infection of the treated plantss in % and 4 B corresponds to the fungicidal infection of the untreated (comntrol) plants in %

oo PF 54900 @® 11

An efficacy of 0 meanss that the infection level of the tre ated plants corresponds to that of the untreated control plants; an efficacy of 100 mearas that the treated plants were not infected.

The expected efficacie=s of the mixtures of active compounds are determined using

Colby’s formula (Colby, S.R. “Calculating synergistic ard antagonistic responsess of herbicide combinationss”, Weeds 15, 20-22, 1967) and ccompared with the obserwed efficacies.

Colby’s formula:

E=x+y-xy/100

E expected efficac y, expressed in % of the untreatead control, when using the mix- ture of the actives compounds A and B at the concentrations a and b

X efficacy, expresssed in % of the untreated control, when using active comp ound A at the concentration a vy efficacy, expresssed in % of the untreated control, when using active comp ound B at the concentration b

The comparative compoounds used were compounds A_ and B, known from the c=aptan mixtures described in EP-A 988 790:

CH,

CF

=

On FF

N~ A NN" B

N™ y N ¢ ¢ — ] — ~ F

PF 54900 ) C 12

Table A — Individmual active compounds

Rl = Cl

Example Ac tive compound compound ir the spray . control liquor Cppm] comtolGmiedted) | Gokieain)

ENE

16 21 63 35

EN ECON BH

168

A 18 35

Compearative compound 63 61

IC i =H

Table B — Mixtures according to the invention cormcentration; mixing ratio

I+lla 7 63+16 ppm 91 48

HEE EE

I+lla 16+63 ppm 87 49

HE

I+lIb 63 + 16 ppm 48 4:1 +1ib 16 + 63 ppm 74 28 1:4 *) efficacy calculaated using Colby’s formula

© P F54900

Taable C — comparative tests — combimations of the active compounds knovawn from EP-A 9&38 790

Observed efficacy | Calculated efficacy”) concentration; mixing ratio

A+ lla 4:1

A+ lla 12 16+63 ppm 35 57 1:4

A+ lib 13 63 + 16 ppm 48 61

ERE

A+llb 14 16 + 63 ppm 35

EE ENN

B+ lla 15 63+16 ppm 48 61 ce] Ee |e | ov

B+ lla 16+63 ppm 35

EE

B+ lib 17 63 + 16 ppm 48 61 cee |e

B+ Ib 16 + 63 ppm 48 1:4 *) efficacy calculated using Colby’s formula

Tite test results show that the mixture s according to the invention have, at comparable application rates, considerably higher activity than the captan mixtures known from

EP A 988 790, even though the comparative compounds, as individual acti~ve com- pounds, are more active than compound 1. “C=omprises/comprising” when used in this specification is taken to specify the pres- ermce of stated features, integers, steps or components but does not preclucie the pres- ermce or addition of one or more other features, integers, steps or componemnts or greoups thereof.

AMENDED SSHEET

Claims (22)

"PF 54900 We claim:

1. A fungiacidal mixture, which mixture comprises ) 1) the triazolopyrimidine derivative of the forsmula CH, Or F N l ON EN NP? a and 2) a phthalimide derivative il selected from the group consisting of a) captan of the formula lla, 8] CL psec, lla oO and b) folpet of the faormuia tib, 0 CI seen lib 0] in =a synergistically effective amount.

2. A “fungicidal mixture as claimed in claim 1 comprising the compound of the for— mwa | and the compound of the formula ll in a weight ratio of from 100:1 to 1: 100.

3. A fungicidal mixture as claimed in claim 1 or 2 comprising, as phthalimide dervuva- tiwve, captan of the formula lla as set forth in claim 1.

4. A= fungicidal mixture as claimed in claim 1 or 2 comprising, as phthalimide dewriva- tuve, folpet of the formula lib as set forth in claim 1. AMENDED SHEET

"PF 54900

5. A fungicid ai composition comprising a liquid or solid carrier and a mixture as claimed irm any one of claims 1 to 4.

6. A method for controlling rice-pathogenic harmful fungi, which comprises treatirg the fungi, their habitat or the seed, the soil or the plants to be protected againsst fungal att=ack with an effective amount of the= compound | and one of the com- pounds Il as set forth in claim 1.

7. A method according to claim 6, wherein the compounds | and Il as set forth in claim 1 are applied simultaneously, that is jointly or separately, or in successicn.

8. A method according to claim 6, wherein the mixture as claimed in any one of claims 1 t=0 4 is applied in an amount of fron 5 g/ha to 2000 g/ha. 16

9. A method according to claim 6 or 7, whereir the mixture as claimed in any one of claims 1 t.0 4 is applied in an amount of from 1 to 1000 g/100 kg of seed.

10. A method according to any one of claims 5 #o 8, wherein the harmful fungus Pyriculari.a oryzae is controlled.

11. Seed comprising the mixture as claimed in &ny one of claims 1 to 4 in an amo-unt of from 1 to 1000 g/100 kg.

12. The use Of the compound | and the compouwand [I as set forth in claim 1 for pre par- ing a composition suitable for controlling ha rmful fungi.

13. A fungicidal mixture as claimed in any one of claims 1 to 4, substantially as here- inbefore cdescribed or exemplified.

14. A fungicidal mixture including any new and inventive integer or combination of integers, substantially as herein described.

156. A fungicidal composition as claimed in clairn 5, substantially as hereinbefore cde- scribed o=r exemplified.

16. A fungiciedal composition including any new and inventive integer or combinat®on of integers, substantially as herein describe=d.

17. A method according to the invention for cortrolling rice-pathogen harmful funggi, 40 substantaally as hereinbefore described or eexempiified. AMENDED SEXET

PF 549800

18. A method for controlling rice-pathogen hamnful fungi including any neve and in- ve=ntive integer or combination of integers, substantially as herein described.

19. Seeed as claimed in claim 11, substantially as hereinbefore described cr exempli- fiexd.

20. Seeed according to the invention includ@ng any new and inventive integ er or com- b& nation of integers, substantially as hexrein described.

21. The use of the compound | and compound Il as claimed in claim 12, s ubstantially ass hereinbefore described or exemplified.

22. Thhe use of the compound | and compoeund Il including any new and in ventive integer or combination of integers, sub stantially as herein described. AMENDED SFeZT

’ PF 54900

Fungicidal mixtures for fighti ng against rice pathogens Abstract Fungicidal mixtures for controlling rice pathogens, which mixtures comprise, as active components, 1) the triazolopyrimidine «derivative of the formula |, S F N F — F N">NT"al and 2) a phthalimide derivative Il selected from the group consisting of a) captan of the formula ila, 0 TT psec lla 0) and b) folpet of the forrmula lib, 0] I sen lib 0] in a synergistically effective amount, methods for controllirmg rice pathogens using mix- tures of the compound | with the compounds II, the use of the compound | with the compounds Il for preparing such mixtures and compositioras comprising these mixtures are described.