WO2007141010A1

WO2007141010A1 - A method of protecting a plant propagation material, a plant, parts of a plant and/or plant organs

Info

Publication number: WO2007141010A1
Application number: PCT/EP2007/005021
Authority: WO
Inventors: Ronald Zeun; Fredrik Cederbaum; Michael Oostendorp
Original assignee: Syngenta Participations AG
Current assignee: Syngenta Participations AG
Priority date: 2006-06-08
Filing date: 2007-06-06
Publication date: 2007-12-13
Anticipated expiration: 2008-12-08

Abstract

A method of controlling or preventing pathogenic damage or pest damage in a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time, which comprises applying on the plant propagation material a compound of formula (I) or an enantiomer, diastereomer, or agronomically acceptable salt thereof, and optionally together with additional pesticides, wherein the plant is a cereal, beet, leguminous plant, oil plant, cucumber plant, fibre plant, vegetable, or an ornamental.

Description

A METHOD OF PROTECTING A PLANT PROPAGATION MATERIAL. A PLANT. PARTS OF

A PLANT AND/OR PLANT ORGANS

The present invention relates to a method for using a defined compound in the control or prevention of pathogenic damage, in particular in a plant propagation material, plant, parts of a plant and plant organs that grow at a later point in time by applying the compound on to the plant propagation material, plant propagation material compositions thereof and combinations of such a compound with certain pesticides, especially for plant propagation material treatment.

The treatment of plant propagation material is a targeted pesticide application which addresses the need for a reduction of environmental and worker exposure compared to foliar or soil pesticide applications.

Pesticidal active ingredients and combinations thereof for controlling pathogens and pests in plant propagation materials and plant organs that grow at a later point in time are described in the literature. The biological properties of those known compounds and combinations are not entirely satisfactory in the areas of pathogenic control, phytotoxicity, and environmental and worker exposure, for example. In particular, in the instance a pathogen has become, or risks becoming resistant to the previously known combinations, improved methods of control or prevention are sought.

There is a continuing need to provide pesticidal compositions, which provide improved, for example, biological properties, especially for controlling pathogens.

EP0975634 and US 6297251 disclose a number of heterocyclic substituted triazolopyrimidine compounds as having biological properties for fungi control.

WO 2005/060751 , WO 2004/045282 and WO 2004/064519 disclose certain fungicide mixtures of a defined heterocyclic substituted triazolopyrimidine compound.

It has now been found that a certain substituted triazolopyrimidine compound has unexpectedly good activity when applied onto a plant propagation material. Accordingly, in a first aspect, the present invention provides a method of controlling or preventing pathogenic 71173FF

-2- damage or pest damage in a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time, which comprises applying on the plant propagation material a compound of formula I

or an enantiomer, diastereomer, or agronomically acceptable salt thereof, wherein the plant is a cereal, beet, leguminous plant, oil plant, cucumber plant, fibre plant, vegetable, or an ornamental.

In a second aspect, the present invention provides a method of controlling or preventing pathogenic damage damage in a plant propagation material, parts of a plant a plant, and/or plant organs that grow at a later point in time, which comprises applying on the plant propagation material a compound defined in the first aspect.

In a third aspect, the present invention provides a method of protecting a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time against pathogenic damage damage by applying to the plant propagation material a compound defined in the first aspect.

The invention also relates to a plant propagation material treated with the compound defined in the first aspect.

The present invention also relates to a method which comprises (i) treating a plant propagation material, such as a seed, with a compound as defined in the first aspect, and (ii) planting or sowing the treated propagation material, wherein the compound protects against pathogenic damage of the treated plant propagation material, parts of plant, plant organs and/or plant grown from the treated propagation material. 71173FF

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Further, the present invention concerns a method which comprises (i) treating a plant propagation material, such as a seed, with a compound as defined in the first aspect, and (ii) planting or sowing the treated propagation material, and (iii) achieving protection against pathogenic damage of the treated plant propagation material, parts of plant, plant organs and/or plant grown from the treated propagation material.

In a preferred embodiment, a stereoisomeric or diastereomeric mixture of compound of formula I is applied on the plant propagation material.

According to the instant invention, a "stereoisomeric or diastereomeric mixture" of two stereoisomers or diastereomers or a "stereoisomeric or diastereomeric compound" means a mixture of two stereoisomers or diastereomers in a ratio from 1 :10 to 10:1. Accordingly, ratio of compound of formula Ia (stereoisomer a) to compound of fomula 1 b (stereoisomer b) can be from 1 :10 to 10:1 , preferably 1 :5 to 5:1 , more preferably 3:1 to 1 :3, such as 2.5:1 to 1.5:1.

In a further aspect of the invention, the compound of formula 1 is present in the form of a plant propagation material, preferably seed, treatment composition, wherein the composition optionally further comprises one or more customary formulation auxiliaries.

In an embodiment of each aspect, a combination comprising the compound defined in the first aspect and one or more pesticides are applied on the plant propagation material, in any desired sequence or simultaneously.

In the event a combination is used, the compound of formula I and one or more pesticides are present in the form of a plant propagation material, preferably seed, treatment composition, wherein the composition optionally further comprises one or more customary formulation auxiliaries.

Examples of pesticides include fungicides, bactericides, insecticides, acaricides and nematicides. A preferred pesticide for use in combination with a compound of formula I is a fungicide.

Suitable examples of fungicides are fludioxonil, penthiopyrad, prothioconazole, flutriafol, azoxystrobin, cyproconazole, cyprodinil, diniconazole, difenoconazole, fludioxonil, 71173FF

-4- fluoxastrobin, trifloxystrobin, metalaxyl, metalaxyl-M (mefenoxam), fluquinconazole, fenarimol, nuarimol, pyrifenox, thiabendazole, tebuconazole, triadimenol, benalaxyl, benalaxyl-M, benomyl, carbendazim, carboxin, flutolanil, fuberidazole, guazatin, ipconazole, iprodione, pencycuron, propamocarb, silthiofam, thiram, triazoxide, triticonazole, a manganese compound (such as mancozeb, maneb), bitertanol, captan, imazalil, metconazole, prochloraz, prothioconazole, pyraclostrobin, triticonazole, tetraconazole, tolylfluanid, boscalid, myclobutanil, fluopyram, compound α is represented

compound β represented by

a compound of formula A

or a tautomer of such a compound, and a and a compound of formula B 71173FF

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, or a tautomer of such a compound.

The compound of formula A can occur in different stereoisomeric forms, which are described in formulae Ai, An, Am and A|_V:

The invention covers all such stereoisomers and mixtures thereof in any ratio with a combination of compound of formula I, and stereoisomers and mixtures thereof.

In an embodiment, compound A is a compound of the formula Aa (trans) 71173FF

-6-

which represents a compound of formula A_t, a compound of formula A_M or a mixture in any ratio of a compound of formula A| and a compound of formula An.

In an embodiment, compound A is a compound of the formula Ab (cis)

which represents a compound of formula Aim, a compound of formula A|_V or a mixture in any ratio of a compound of formula Am and a compound of formula A_iV.

In a preferred embodiment compound A is a racemic mixture of compound formula A, wherein the weight ratio of racemic compounds of formula Aa, which represent a racemic mixture of compounds of formula Ai and compounds of formula An, to racemic compounds of formula Ab, which represent a racemic mixture of compounds of formula A_m and compounds of formula Aιv, is from 1 : 1 to 100. Suitable examples of weight ratios of compound of formula Aa to Ab in a racemic mixture are 1 :1 , 2:1 , 3:1 , 4:1 , 5:1 , 6:1 , 7:1 , 8:1 , 9:1 , 10:1 , 20:1 , 50:1 or 100 : 1. Preference is given to ratios from 2:1 to 100:1 , more preferably 4:1 to 10:1.

In an especially preferred embodiment compound A is a racemic mixture, wherein the content of racemic compound of formula Aa, which represent a racemic mixture of compounds of formula A_t and compounds of formula A_M, is from 65 to 99 % by weight. 71173FF

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In the instance of an insecticide, acaricide and/or nematcide, is also used in the present invention the biological spectrum of the combination is broadened to such an extent that the combination demonstrates activity against damage caused by a pest, such as an animal pest.

Suitable examples of insecticides, acaricides and nematicides include thiamethoxam, imidacloprid, clothianidin, lamda-cyhalothrin, tefluthrin, β-cyfluthrin, permethrin, abamectin, fipronil, spinosad, flubendamide and a compound of formula A-1

A compound of formula I and its manufacturing processes starting from known and available compounds are described in EP-0975634 and US 6297251. The compound α is described in WO2002012172 and is registered under CAS 366815-39-6, preferably 366815-39-6 (E₁E₁E). The compound β is described in EP-1 -035-122 and is registered under CAS 847749-37-5, CAS-291771 -99-8 and CAS-291771 -83-0. The compound of formula B is described in WO 03/010149 and WO 05/58839. The compounds of formula A and its manufacturing processes starting from known and commercially available compounds is described in WO 03/074491 , WO 2006/015865 and WO 2006/015866. The compound of formula A-1 is described in WO- 03/015519

Details (e.g., structure, chemical name, commercial names, etc) of each of the pesticides with a common name can be found in the e-Pesticide Manual, version 3.1 , 13th Edition, Ed. CDC Tomlin, British Crop Protection Council, 2004-05.

Controlling, preventing or protecting and its inflections, within the context of the present invention, mean reducing any undesired effect, such as

- pathogenic, such as phytopathogenic, especially fungi, infestation or attack of, and

- pathogenic damage or pest damage on, 71173FF

-8- a plant, part of the plant or plant propagation material to such a level that an improvement is demonstrated.

The compounds defined in the first aspect and combinations thereof, particularly when applied to plant propagation material, especially seed, can have very advantageous properties for protecting plants against (i) pathogenic, such as phytopathogenic, especially fungi, attack or infestation, which result in a disease and damage to the plant and/or (ii) pest attack or damage in the instance a pesticide that is, for example, an insecticide, acaricide and/or nematcide is also present; the present invention can control or prevent pathogenic damage and/or pest damage on a seed, parts of plant and/or plant grown from the treated seed. In some cases, control against pest attack or damage also indirectly results in control against pathogenic attack, and vice-a-versa.

These properties can be for example the unexpected enhanced action resulting in lower pathogenic damage and/or pest damage, lower rates of application, or a longer duration of action. In the instance of agriculture, the enhanced action is found to show an improvement in the growing characteristics of a plant by, for example, higher than expected control of the pathogenic infestation and/or pest damage.

The improvement in the growing (or growth) characteristics of a plant can manifest in a number of different ways, but ultimately it results in a better product of the plant. It can, for example, manifest in improving the yield and/or vigour of the plant or quality of the harvested product from the plant, which improvement may not be connected to the control of diseases and/or pests.

As used herein the phrase "improving the yield" of a plant relates to an increase in the yield of a product of the plant by a measurable amount over the yield of the same product of the plant produced under the same conditions, but without the application of the subject method. It is preferred that the yield be increased by at least about 0.5%, more preferred that the increase be at least about 1 %, even more preferred is about 2%, and yet more preferred is about 4%, or more. Yield can be expressed in terms of an amount by weight or volume of a product of the plant on some basis. The basis can be expressed in terms of time, growing area, weights of plants produced, amount of a raw material used, or the like. 71173FF

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As used herein the phrase "improving the vigour" of a plant relates to an increase or improvement of the vigour rating, or the stand (the number of plants per unit of area), or the plant height, or the plant canopy, or the visual appearance (such as greener leaf colour), or the root rating, or emergence, or protein content, or increased tillering, or bigger leaf blade, or less dead basal leaves, or stronger tillers, or less fertilizer needed, or less seeds needed, or more productive tillers, or earlier flowering, or early grain maturity, or less plant verse (lodging), or increased shoot growth, or earlier germination, or any combination of these factors, or any other advantages familiar to a person skilled in the art, by a measurable or noticeable amount over the same factor of the plant produced under the same conditions, but without the application of the subject method.

When it is said that the present method is capable of "improving the yield and/or vigour" of a plant, the present method results in an increase in either the yield, as described above, or the vigor of the plant, as described above, or both the yield and the vigor of the plant.

Accordingly, the present invention also provides a method of improving the growing characterictics of a plant, which comprises applying to a plant propagation material the compound of the first aspect or a combination thereof, in any desired sequence or simultaneously.

When the compound of formula I is used in combination with one or more pesticides, a synergistically enhanced activity can be observed.

One embodiment includes combinations for application to plant propagation material comprising a compound of formula I and a compound of formula A; a compound of formula I and a compound of formula B; a compound of formula I and azoxystrobin; a compound of formula I and trifloxystrobin; a compound of formula I and cyprodinil; a compound of formula I and bitertanol; a compound of formula I and iprodione; a compound of formula I and mefenoxam; a compound of formula I and prothioconazole; a compound of formula I and thiabendazole; a compound of formula I and metconazole; a compound of formula I and pyraclostrobin; a compound of formula I and boscalid; a compound of formula I and penthiopyrad; a compound of formula I and triticonazole; a compound of formula I and fluoxastrobin; a compound of formula I and fluquinconazole; a compound of formula I and 71173FF

-10- flutriafol; a compound of formula I and guazatine; a compound of formula I and difenoconazole; a compound of formula I and prochloraz; a compound of formula I and ipconazole; a compound of formula I and fludioxonil; a compound of formula I and myclobutanil; or a compound of formula I and tebuconazole; are preferred according to the invention.

The compound of formula I and combinations thereof are effective against phytopathogenic fungi, especially occurring in plants, including seedbome fungi and belong to the following classes: Ascomycetes (e.g. Penicillium, Gaeumannomyces graminis); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Puccinia); Fungi imperfecti (e. g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Altemaria, Pyricularia and Pseudocercosporella herpotrichoides); Oomycetes (e. g. Phytophthora, Peronospora, Bremia, Pythium, Plasmopara); Zygomycetes (e.g., Rhizopus spp.). A combination is especially effective against Alternaria spp., Ascochyta spp., Aspergillus spp., Claviceps purpurea, Cochliobolus spp., Colletotrichum spp., Diplodia maydis, Erysiphe graminis, Fusarium spp. (such as Fusarium culmorum, Fusarium oxysporum, Fusarium solani, Fusarium graminearum and Fusarium moniliforme, Fusarium subglutinans), Gaeumannomyces graminis, Giberella fujikuroi, Giberella zeae, Helminthosporium spp. (such as Helminthosporium graminearum, Helminthosporium oryzae, Helminthosporium solani), Monographella nivalis, Penicillium spp., Puccinia spp., Pyrenophora spp. (such as Pyrenophora graminea), Peronosclerospora spp., Peronspora spp., Phakopsora pachyrhizi, Phythium spp., Phoma spp., Phomopsis spp., Rhizoctonia spp. (such as Rhizoctonia cerealis, Rhizoctonia solani), Septoria spp., Pseudocercosporella spp., Tilletia spp., Rhizopus spp., Thielaviopsis basicola, Typhula spp., Ustilago spp., Sphacelotheca spp. (e.g. Spacelotheca reilliani), Thanatephorus cucumeris, and Verticillium spp..

In the event a combination of the invention also includes a pesticide other than fungicide, such as an insecticide, nematicide, miticide, or acaracide (such as abamectin, imidacloprid, tefluthrin, lambda-cyhalothrin) then the pesticide spectrum of the combination is broadened to include pest control, such as control of pests selected from Nematoda, lnsecta and Arachnida. One embodiment includes combinations comprising a compound of formula I and thiamethoxam; a compound of formula I and imidacloprid, a compound of formula I and abamectin; a compound of formula I and tefluthrin; a compound of formula I and lambda- 71173FF

-11- cyhalothrin; a compound of formula I and clothianidin; a compound of formula I and flubendamide; or a compound of formula I and a compound of formula A-1

In that instance, the combination can also be applied on the pest to control or prevent pest damage and protect the desired material (e.g. plant propagation material, plant and parts of plant) from pest damage. Examples of pests include: from the order Lepidoptera, for example, Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyrotaenia spp., Autographa spp., Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolomia spp., Cryptophlebia leucotreta, Crysodeixis includens, Cydia spp., Diatraea spp., Diparopsis castanea, Earias spp., Elasmopalpus spp., Ephestia spp., Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., HeIIuIa undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypiella, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni and Yponomeuta spp.; from the order Coleoptera, for example, Agriotes spp., Anthonomus spp., Atomaria linearis, Ceutorhynchus spp., Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Gonocephalum spp., Heteronychus spp., Leptinotarsa decemlineata, Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchus spp., Phlyctinus spp., Phyllotreta spp., Popillia spp., Protostrophus spp., 71173FF

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Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Tribolium spp. and Trogoderma spp.; from the order Orthoptera, for example, Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; from the order Isoptera, for example, Reticulitermes spp.; from the order Psocoptera, for example, Liposcelis spp.; from the order Anoplura, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; from the order Mallophaga, for example, Damalinea spp. and Trichodectes spp.; from the order Thysanoptera, for example, Frankliniella spp., Hercinothrips spp., Taeniothrips spp., Thrips palmi, Thrips tabaci and Scirtothrips aurantii; from the order Heteroptera, for example, Dichelops melacanthus, Distantiella theobroma, Dysdercus spp., Euchistus spp., Eurygaster spp., Leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp. and Triatoma spp.; from the order Homoptera, for example, Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidum, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp., Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Paratoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri; from the order Hymenoptera, for example, Acromyrmex, Athalia rosae, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.; from the order Diptera, for example, Antherigona soccata, Bibio hortulanus, , Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp., Drosophila melanogaster, , Liriomyza spp., , Melanagromyza spp., , Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp.,; from the order Acarina, for example, Acarus siro, Aceria sheldoni, Aculus schlechtendali, Amblyomma spp., Argas spp., , Brevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus carpini, Eriophyes spp., Hyalomma spp., Olygonychus pratensis, Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, 71173FF

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Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Tarsonemus spp. and Tetranychus spp.; and from the class Nematoda, for example, the species of Meloidogyne spp. (for example, Meloidogyne incoginita and Meloidogyne javanica), Heterodera spp. (for example, Heterodera glycines, Heterodera schachtii, Heterodora avenae and Heterodora trifolii), Globodera spp. (for example, Globodera rostochiensis), Radopholus spp. (for example, Radopholus similes), Rotylenchulus spp., Pratylenchus spp. (for example, Pratylenchus neglectans and Pratylenchus penetrans), Aphelenchoides spp., Helicotylenchus spp., Hoplolaimus spp., Paratrichodorus spp., Longidorus spp., Nacobbus spp., Subanguina spp. Belonlaimus spp., Criconemella spp., Criconemoides spp. Ditylenchus spp., Dolichodorus spp., Hemicriconemoides spp., Hemicycliophora spp., Hirschmaniella spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., Quinisulcius spp., Scutellonema spp., Xiphinema spp., and Tylenchorhynchus spp.

A preferred emobodiment of the invention relates to a combination comprising compound I and one or more insecticide, nematicide, miticide, or acaracide, optionally further comprising one or more fungicides.

Specific preferred combinations of compound I with an insecticide, nematicide, miticide, and/or acaracide and fungicide are set forth below using the designations provided in Table 1 , wherein, column A designates insecticide, nematicide, miticide, or acaracide (e.g. thiamethoxam is (A)1 ) and column B designates a fungicide acaracide (e.g. azoxystrobin is (B)2). A skilled person would appreciate that the present invention includes each and every combination of active ingredients from any one or more compounds from columns A & B and compound I.

71173FF

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Specific examples of combinations are compound I and

(A)1 +(B)1 ; or (A)1 +(B)2; or (A)1 +(B)3; or (A)1 +(B)4; or (A)1 +(B)5; or (A)1 +(B)6; or (A)1 +(B)7; or (A)1 +(B)8; or (A)1 +(B)9; or (A)1 +(B)10; or (A)1 +(B)11 ; or (A)1 +(B)12; or (A)1 +(B)13; or (A)1 +(B)14; or (A)1 +(B)15; or (A)1 +(B)16; or (A)1 +(B)17; or (A)1 +(B)18; or (A)1 +(B)19; or (A)1 +(B)20; or (A)1+(B)21 ; or (A)1 +(B)22; or (A)1+(B)23; or (A)1+(B)24; or (A)2+(B)1 ; or (A)2+(B)2; or (A)2+(B)3; or (A)2+(B)4; or (A)2+(B)5; or (A)2+(B)6; or (A)2+(B)7; or (A)2+(B)8; or (A)2+(B)9; or (A)2+(B)10; or (A)2+(B)1 1 ; or (A)2+(B)12; or (A)2+(B)13; or (A)2+(B)14; or (A)2+(B)15; or (A)2+(B)16; or (A)2+(B)17; or (A)2+(B)18; or (A)2+(B)19; or (A)2+(B)20; or (A)2+(B)21 ; or (A)2+(B)22; or (A)2+(B)23; or (A)2+(B)24; or (A)3+(B)1 ; or (A)3+(B)2; or

(A)3+(B)3; or (A)3+(B)4; or (A)3+(B)5; or (A)3+(B)6; or (A)3+(B)7; or (A)3+(B)8; or (A)3+(B)9; or (A)3+(B)10; or (A)3+(B)11; or (A)3+(B)12; or (A)3+(B)13; or (A)3+(B)14; or (A)3+(B)15; or (A)3+(B)16; or (A)3+(B)17; or (A)3+(B)18; or (A)3+(B)19; or (A)3+(B)20; or (A)3+(B)21; or (A)3+(B)22; or (A)3+(B)23; or (A)3+(B)24; or (A)4+(B)1; or (A)4+(B)2; or (A)4+(B)3; or (A)4+(B)4; or (A)4+(B)5; or (A)4+(B)6; or (A)4+(B)7; or (A)4+(B)8; or (A)4+(B)9; or (A)4+(B)10; or (A)4+(B)11 ; or (A)4+(B)12; or (A)4+(B)13; or (A)4+(B)14; or (A)4+(B)15; or (A)4+(B)16; or (A)4+(B)17; or (A)4+(B)18; or (A)4+(B)19; or (A)4+(B)20; or (A)4+(B)21 ; or (A)4+(B)22; or (A)4+(B)23; or (A)4+(B)24; or (A)5+(B)1; or (A)5+(B)2; or (A)5+(B)3; or (A)5+(B)4; or (A)5+(B)5; or (A)5+(B)6; or (A)5+(B)7; or (A)5+(B)8; or (A)5+(B)9; or (A)5+(B)10; or (A)5+(B)11; or (A)5+(B)12; or (A)5+(B)13; or (A)5+(B)14; or (A)5+(B)15; or (A)5+(B)16; or (A)5+(B)17; or (A)5+(B)18; or (A)5+(B)19; or (A)5+(B)20; or (A)5+(B)21 ; or (A)5+(B)22; or (A)5+(B)23; or (A)5+(B)24; or (A)6+(B)1 ; or (A)6+(B)2; or (A)6+(B)3; or (A)6+(B)4; or (A)6+(B)5; or (A)6+(B)6; or (A)6+(B)7; or (A)6+(B)8; or (A)6+(B)9; or (A)6+(B)10; or (A)6+(B)11 ; or (A)6+(B)12; or (A)6+(B)13; or (A)6+(B)14; or (A)6+(B)15; or (A)6+(B)16; or 71173FF

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(A)6+(B)17; or (A)6+(B)18; or (A)6+(B)19; or (A)6+(B)20; or (A)6+(B)21 ; or (A)6+(B)22; or (A)6+(B)23; or (A)6+(B)24; or (A)7+(B)1; or (A)7+(B)2; or (A)7+(B)3; or (A)7+(B)4; or (A)7+(B)5; or (A)7+(B)6; or (A)7+(B)7; or (A)7+(B)8; or (A)7+(B)9; or (A)7+(B)10; or (A)7+(B)11; or (A)7+(B)12; or (A)7+(B)13; or (A)7+(B)14; or (A)7+(B)15; or (A)7+(B)16; or (A)7+(B)17; or (A)7+(B)18; or (A)7+(B)19; or (A)7+(B)20; or (A)7+(B)21 ; or (A)7+(B)22; or (A)7+(B)23; or (A)7+(B)24; or (A)8+(B)1 ; or (A)8+(B)2; or (A)8+(B)3; or (A)8+(B)4; or (A)8+(B)5; or (A)8+(B)6; or (A)8+(B)7; or (A)8+(B)8; or (A)8+(B)9; or (A)8+(B)10; or (A)8+(B)11 ; or (A)8+(B)12; or (A)8+(B)13; or (A)8+(B)14; or (A)8+(B)15; or (A)8+(B)16; or (A)8+(B)17; or (A)8+(B)18; or (A)8+(B)19; or (A)8+(B)20; or (A)8+(B)21; or (A)8+(B)22; or (A)8+(B)23; or (A)8+(B)24; or (A)9+(B)1 ; or (A)9+(B)2; or (A)9+(B)3; or (A)9+(B)4; or (A)9+(B)5; or (A)9+(B)6; or (A)9+(B)7; or (A)9+(B)8; or (A)9+(B)9; or (A)9+(B)10; or (A)9+(B)11 ; or (A)9+(B)12; or (A)9+(B)13; or (A)9+(B)14; or (A)9+(B)15; or (A)9+(B)16; or (A)9+(B)17; or (A)9+(B)18; or (A)9+(B)19; or (A)9+(B)20; or (A)9+(B)21; or (A)9+(B)22; or (A)9+(B)23; or (A)9+(B)24; or (A)10+(B)1; or (A)10+(B)2; or (A)10+(B)3; or (A)10+(B)4; or (A)10+(B)5; or (A)10+(B)6; or (A)10+(B)7; or (A)10+(B)8; or (A)10+(B)9; or (A)10+(B)10; or

(A)10+(B)11 ; or (A)10+(B)12; or (A) 10+(B) 13; or (A) 10+(B) 14; or (A)10+(B)15; or (A)10+(B)16; or (A)10+(B)17; or (A)10+(B)18; or (A)10+(B)19; or (A)10+(B)20; or (A)10+(B)21 ; or (A)10+(B)22; or (A)10+(B)23; or (A)10+(B)24; or (A)11+(B)1 ; or (A)11 +(B)2; or (A)1 1 +(B)3; or (A)11 +(B)4; or (A)11 +(B)5; or (A)1 1 +(B)6; or (A)11 +(B)7; or (A)1 1 +(B)8; or (A)11 +(B)9; or (A)1 1 +(B)10; or (A)1 1 +(B)11 ; or (A)11 +(B)12; or (A)11 +(B)13; or (A)11 +(B)14; or (A)1 1 +(B)15; or (A)11 +(B)16; or (A)1 1 +(B)17; or (A)1 1 +(B)18; or (A)11 +(B)19; or (A)1 1 +(B)20; or (A)11 +(B)21 ; or (A)1 1 +(B)22; or (A)11 +(B)23; or (A)11 +(B)24; or (A)12+(B)1 ; or (A)12+(B)2; or (A)12+(B)3; or (A)12+(B)4; or (A)12+(B)5; or (A)12+(B)6; or (A)12+(B)7; or (A)12+(B)8; or (A)12+(B)9; or (A)12+(B)10; or (A)12+(B)11 ; or (A)12+(B)12; or (A)12+(B)13; or (A)12+(B)14; or (A)12+(B)15; or (A)12+(B)16; or (A)12+(B)17; or (A)12+(B) 18; or (A)12+(B)19; or (A)12+(B)20; or (A)12+(B)21 ; or (A)12+(B)22; or (A)12+(B)23; or (A)12+(B)24.

The compound of formula I and combinations thereof can be formulated for a particular use. Preferably, the compound of formula I and combinations thereof can be formulated for protecting cultivated plants or their propagation materials. In an embodiment, the combination of the invention can be applied to the plant in a conventional manner, such as foliar spray. Advantageously, the combinations are formulated for plant propagation material, preferably seed, treatment applications for controlling or preventing damage by pests and/or pathogens, 71173FF

-16- which are found in agriculture and forestry, and can particularly damage the plant in the early stages of its development.

Further, the present invention also envisages soil application of the combinations of the invention to control the soil-dwelling pests and/or soil-borne pathogens. Methods of applying to the soil can be via any suitable method, which ensures that the combination penetrates the soil, for example, nursery tray application, in furrow application, soil drenching, soil injection, drip irrigation, application through sprinklers or central pivot, incorporation into soil (broad cast or in band) are such methods.

The benefit from the invention can also be achieved either by (i) treating plant propagation material with a compound of formula I or a combinaton thereof or (ii) applying to the locus where control is desired, generally the planting site, the compound of formula I or a combinaton thereof, or both (i) and (ii).

The term "plant propagation material" is understood to denote all the generative parts of the plant, such as seeds, which can be used for the multiplication of the latter and vegetative plant material such as cuttings and tubers (for example, potatoes). There may be mentioned, e.g., the seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, parts of plants. Germinated plants and young plants, which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion.

Parts of plant and plant organs that grow at later point in time are any sections of a plant that develop from a plant propagation material, such as a seed. Parts of plant, plant organs, and plants can also benefit from the pathogenic and/or pest damage protection achieved by the application of the combination on to the plant propagation material. In an embodiment, certain parts of plant and certain plant organs that grow at later point in time can also be considered as plant propagation material, which can themselves be applied (or treated) with the combination; and consequently, the plant, further parts of the plant and further plant organs that develop from the treated parts of plant and treated plant organs can also benefit from the pathogenic and/or pest damage protection achieved by the application of the combination on to the certain parts of plant and certain plant organs. 71173FF

-17-

Methods for applying or treating pesticidal active ingredients and mixtures thereof on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting and soaking application methods of the propagation material.

The active ingredients can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.

In a preferred embodiment, the combination is applied or treated on to the plant propagation material by a method such that the germination is not induced; generally seed soaking induces germination because the moisture content of the resulting seed is too high. Accordingly, examples of suitable methods for applying (or treating) a plant propagation material, such as a seed, is seed dressing, seed coating or seed pelleting and the like.

It is preferred that the plant propagation material is a seed. Although it is believed that the present method can be applied to a seed in any physiological state, it is preferred that the seed be in a sufficiently durable state that it incurs no damage during the treatment process. Typically, the seed would be a seed that had been harvested from the field; removed from the plant; and separated from any cob, stalk, outer husk, and surrounding pulp or other non-seed plant material. The seed would preferably also be biologically stable to the extent that the treatment would cause no biological damage to the seed. It is believed that the treatment can be applied to the seed at any time between harvest of the seed and sowing of the seed or during the sowing process (seed directed applications). The seed may also, optionally, be primed either before or after the treatment.

Even distribution of the active ingredients and adherence thereof to the propagation materials is desired during propagation material treatment. Treatment could vary from a thin film (dressing) of the formulation containing the active ingredient(s) on a plant propagation material, such as a seed, where the original size and/or shape are recognizable to an intermediary state (such as a coating) and then to a thicker film (such as pelleting with many layers of different materials (such as carriers, for example, clays; different formulations, such 71173FF

-18- as of other active ingredients; polymers; and colourants) where the original shape and/or size of the seed is no longer recognisable.

The seed treatment occurs to an unsown seed, and the term "unsown seed" is meant to include seed at any period between the harvest of the seed and the sowing of the seed in the ground for the purpose of germination and growth of the plant.

Treatment to an unsown seed is not meant to include those practices in which the active ingredient is applied to the soil but would include any application practice that would target the seed during the planting process.

Preferably, the treatment occurs before sowing of the seed so that the sown seed has been pre-treated with the combination. In particular, seed coating or seed pelleting are preferred in the treatment of the combinations according to the invention. As a result of the treatment, the active ingredients in the combination are adhered on to the seed and therefore available for pest and/or disease control.

The treated seeds can be stored, handled, sowed and tilled in the same manner as any other active ingredient treated seed.

The combination according to the present invention is suitable for plants of the crops: cereals (wheat, barley, rye, oats, corn, rice, sorghum, triticale and related crops); beet (sugar beet and fodder beet); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, sunflowers); cucumber plants (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); as well as ornamentals (flowers, shrubs, broad- leaved trees and evergreens, such as conifers). Especially suitable are wheat, barley, rye, oats, corn and soybean, triticale.

Suitable target crops also include transgenic crop plants of the foregoing types. The transgenic crop plants used according to the invention are plants, or propagation material thereof, which are transformed by means of recombinant DNA technology in such a way that they are - for instance - capable of synthesizing selectively acting toxins as are known, for example, from toxin-producing invertebrates, especially of the phylum Arthropoda, as can be 71173FF

-19- obtained from Bacillus thuringiensis strains; or as are known from plants, such as lectins; or in the alternative capable of expressing a herbicidal or fungicidal resistance. Examples of such toxins, or transgenic plants which are capable of synthesizing such toxins, have been disclosed, for example, in EP-A-O 374 753, WO 93/07278, WO 95/34656, EP-A-O 427 529 and EP-A-451 878 and are incorporated by reference in the present application.

The weight ratio of a compound of formula I with a pesticide is selected as to give the desired, for example, synergistic, action. In general, the weight ratio would vary depending on the specific pesticide and how many pesticides are present in the combination. Generally, in the event the combination consists of two active ingredients the weight ratio is from 100:1 to 1 :100, preferably from 75:1 to 1 :75, more preferably, 50:1 to 1.50, especially 25:1 to 1 :25, advantageously 10:1 to 1 :10.

The rates of application (use) of the compound of formula I alone or in combination with one or more pesticides vary, for example, according to type of use, type of crop, the specific active ingredients in the combination, type of plant propagation material but is such that the active ingredients in the combination is an effective amount to provide the desired enhanced action (such as disease or pest control) and can be determined by trials.

Generally for seed treatment, application rates can vary from 0.5 to 1000g / 100kg of seeds of active ingredients.

Suitable seed treatment application rates of (I) a compound of formula I tend to be 1 - 300, preferably 2 - 200, more preferably 2.5 - 4Og /100kg of seeds, and if one or more pesticides are also present, then rates tend to be 1 -700, preferably 2-550, more preferably 2 - 450, g/100kg of seeds of any other pesticides.

The plant propagation material treated by a compound of formula I or combination thereof of the present invention are, therefore, resistant to disease and/or pest damage; accordingly, the present invention also provides a pathogenic and/or pest resistant plant propagation material which is treated with compound of formula I or the combination thereof and consequently at least the active ingredients thereof are adhered on the propagation material, such a seed. 71173FF

-20-

The seed treatment combination and composition can also comprise or may be applied together and/or sequentially with further active compounds. These further compounds can be other pesticidal active ingredients, fertilizers or micronutrient donors or other preparations that influence plant growth, such as inoculants.

A single pesticidal active ingredient may have activity in more than one area of pest control, for example, a pesticide may have fungicide, insecticide and nematicide activity. Specifically, aldicarb is known for insecticide, acaricide and nematicide activity, while metam is known for insecticide, herbicide, fungicide and nematicide activity, and thiabendazole and captan can provide nematicide and fungicide activity.

The combination of the present invention may be mixed with other pesticides, such as fungicides, insecticides and nematicides.

Suitable examples include triazole derivatives, strobilurins, carbamate (including thiocarbamate), benzimidazoles (thiabendazole), N-trihalomethylthio compounds (captan), substituted benzenes, carboxamides, phenylamides and phenylpyrroles, and mixtures thereof; and neonicotinoids, carbamates and pyrethroids.

A compound of formula I and the pesticide(s) may be used either in pure form, i.e., as a solid active ingredient, for example, in a specific particle size, or preferably together with at least one of the auxiliary (also known as adjuvants) customary in formulation technology, such as extenders, e.g., solvents or solid carriers, or surface-active compounds (surfactants), in the form of a formulation, in the present invention. Generally, the compound and pesticide(s) are in the form of a formulation composition with one or more of customary formulation auxiliaries.

Therefore, the combination is normally used in the form of formulations. The compound of formula I and the pesticide(s) making-up the combination can be applied to the locus where control is desired either simultaneously or in succession at short interval, for example on the same day, if desired together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology. In a preferred embodiment, the combinations are applied simultaneously.

In the event the combination is applied simultaneously in the present invention, they may be 71173FF

-21- applied as a composition, in which case the compound of formula I and the pesticide(s) can be obtained from a separate formulation source and mixed together (known as a tank-mix, ready- to-apply, spray broth, or slurry), optionally with other pesticides, or they can be obtained as single formulation mixture source (known as a pre-mix, concentrate, formulated compound (or product)), and optionally mixed together with other pesticides.

In an embodiment, the combination of the present invention is applied as a composition.

In a preferred embodiment of the invention, the composition is a pre-mix composition (or mixture).

Whereas, examples of seed treatment formulation types for pre-mix compositions are: WS: wettable powders for seed treatment slurry LS: solution for seed treatment ES: emulsions for seed treatment

FS: suspension concentrate for seed treatment WG: water dispersible granules, and CS: aqueous capsule suspension.

Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.

As with the nature of the formulations, the methods of application, such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.

Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily ' employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. 71173FF

-22-

The formulations are prepared in known manner, e.g., by homogeneously mixing and/or grinding the active ingredients with extenders, e.g., solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates, such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, as well as vegetable oils or epoxidised vegetable oils, such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used, e.g., for dusts and dispersible powders, are normally natural mineral fillers, such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite, and suitable nonsorbent carriers are, for example, calcite or sand. In addition, a great number of pregranulated materials of inorganic or organic nature can be used, e.g., especially dolomite or pulverized plant residues.

Depending upon the nature of the active ingredient compounds to be formulated, suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term "surfactants" will also be understood as comprising mixtures of surfactants.

Particularly advantageous application-promoting adjuvants are also natural or synthetic phospholipids of the cephalin and lecithin series, e.g., phosphatidylethanolamine, phos- phatidylserine, phosphatidylglycerol and lysolecithin.

Normally, a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, active ingredient compounds, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the 71173FF

-23- auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.

Typically, a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, active ingredient compounds, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.

Whereas commercial products will preferably be formulated as concentrates (e.g., pre-mix composition (formulation)), the end user will normally employ dilute formulations (e.g., tank mix composition).

Preferred seed treatment pre-mix formulations are aqueous suspension concentrates. The formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.

The Examples which follow serve to illustrate formulations according to the invention, "active ingredient" denoting a compound of formula I or a combination thereof with another pesticide(s). The Examples are in no way intended to be limiting in nature, i.e., other similar adjuvants known in the art may be substituted for the specifically-disclosed adjuvants provided below.

Formulation Examples

Wettable powders a) b) c) active ingredient 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate - 6 % 10 % phenol polyethylene glycol ether 2 % 71173FF

-24-

(7-8 mol of ethylene oxide) highly dispersed silicic acid 5 % 10 % 10 %

Kaolin 62 % 27 %

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

Powders for dry seed treatment a) b) c) active ingredient 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % -

Kaolin 65 % 40 %

Talcum - 20

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

Emulsifiable concentrate active ingredient 10 % octylphenol polyethylene glycol ether 3 %

(4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 %

Cyclohexanone 30 % xylene mixture 50 %

Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

Dusts a) b) c)

Active ingredient 5 % 6 % 4 %

Talcum 95 %

Kaolin - 94 % mineral filler - - 96 %

Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed. 71173FF

-25-

Extruder granules

Active ingredient 15 % sodium lignosutfonate 2 % carboxymethylcellulose 1 %

Kaolin 82 %

The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

Coated granules

Active ingredient 8 % polyethylene glycol (mol. wt. 200) 3 %

Kaolin 89 % The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

Suspension concentrate active ingredient 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %

Sodium lignosulfonate 10 %

Carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 %

Water 32 %

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

Flowable concentrate for seed treatment active ingredient 40 % propylene glycol 5 % Ό Ό copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 % 71173FF

-26-

1 ,2-benzisothiazolin-3-one (in the form of a 20% solution in 0.5 % water) monoazo-pigment calcium salt 5 %

Silicone oil (in the form of a 75 % emulsion in water) 0.2 %

Water 45.3 %

In a preferred embodiment, each of the combinations of the present invention is a plant propagation material, preferably seed, treating composition.

Using such formulations either straight or diluted, plant propagation material can be treated and protected against damage, for example, from pathogen(s), by, for example, spraying, pouring or immersing.

A compound of formula I and combinations thereof are distinguished by the fact that they are especially well tolerated by plants and are environmentally friendly.

In an embodiment, a compound of formula I or combinations thereof can also be used to treat stored products, such as grain, for protection against pathogens and/or pests.

In each aspect and embodiment of the invention, "consisting essentially" and inflections thereof are a preferred embodiment of "comprising" and its inflections, and "consisting of" and inflections thereof are a preferred embodiment of "consisting essentially of" and its inflections.

The following Examples are given by way of illustration and not by way of limitation of the invention.

Biological Examples

1. Microdochium nivale / wheat (Snow mold on wheat) 71173FF

-27-

After application of the formulated seed treatment onto M. π/Va/e-infected seeds of winter wheat, the seeds are sown in trays filled with planting soil. The trial is kept for 4 weeks in a growth room at 4⁰C and darkness. Then the temperature is increased to 15⁰C and a12hr light period is provided. After development of the primary leaf plants are kept at 10⁰C and high humidity until the trial is finished. The following assessments are made: emergence count, final stand count, number of infected plants.

Compound of formula I @ 20g/100kg: 95% activity

2. Pyrenophora graminea / barley (Stripe disease on barley)

After application of the formulated seed treatment onto P. graminea -infected seeds of winter barley the seeds are sown in trays filled with field soil. The trays are kept in a growth room for 3 weeks at 4⁰C. After this period the trial is transferred to a greenhouse where a temperature of 12⁰C and a 14hr light period is provided. The following assessments are made: emergence count, final stand count, number of infected plants.

Compound of formula I @ 20g/100kg: 64% activity

3. Gaumannomyces graminis I wheat (Take-all on wheat)

After application of the formulated seed treatment onto seeds of winterwheat the seeds are sown in trays filled with field soil. The field soil has been inoculated artificially before sowing with Gaumannomyces graminis by thouroughly mixing mycelium and soil. The trial is kept in a growth room for 5 weeks at 17⁰C and a 14hr light period. The following assessments are made: emergence count, final stand count, disease severity on roots of infected plants. Each number is determined for 30 seeds per treatment.

Compound of formula I @ 100g/100kg: 63% activity

4. Rhizoctonia solani / cotton (Damping off on Cotton)

A defined amount of mycelium of R. solani is blended with soil and trays are filled with the inoculated soil. The formulated test compounds are applied to cotton seeds. The treated cotton seeds are then sown into the inoculated soil. Until germination the test is stored at 20° 71173FF

-28-

C and a rel. humidity of 90% in the dark. After germination the test is transferred to 25° C and a rel. humidity of 70% with a photoperiod of 14h. The evaluation is done by counting the emerged cotton plants and the number of emerged and diseased plants.

Compound of formula I @ 200g/100kg: 60% activity

Claims

71173FF-29-CLAIMS

1. A method of controlling or preventing pathogenic damage or pest damage in a plant propagation material, which comprises applying on the plant propagation material a compound of formula I

2. The method according to claim 1 , wherein a stereoisomeric or diastereomeric mixture of the compound is applied on the plant propagation material.

3. The method according to either claim 1 or claim 2 wherein the plant is wheat, barley, rye, oats, corn and soybean or triticale.

4. The method according to any one of claim 1 to 3, wherein the compound is applied at between 1 to 300 grams per 100 kg of seeds.

5. The method according to any one of claims 1 to 4 wherein one or more pesticides are also applied on the plant propagation material in combination with the compound defined in any one of claims 1 to 3, in any desired sequence or simultaneously.

6. The method according to claim 5 wherein at least one pesticide is an insecticide, acaricide or nematicide.

7. The method according to claims 5 or claim 6 wherein the compound defined in any one of claims 1 to 3 and one or more pesticides are applied simultaneously. 71173FF

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8. The method according to any one of claims 5 to 7 wherein the combination is in the form of a composition, preferably a formulated concentrate composition.

9. A method of protecting a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time against pathogenic damage or pest damage by applying to the plant propagation material a compound defined in any one of claims 1 to 3 or a combination defined in any one of claims 5 to 8.

10. A method of improving the growing characterictics of a plant, which comprises applying to a plant propagation material a compound defined in any one of claims 1 to 3 or a combination defined in any one of claims 5 to 8.

11. The method according to any one of claims 1 to 8, wherein the plant propagation material is a seed.

12. A plant propagation material treatment composition comprising a compound defined in any of claims 1 to 3 and optionally one or more customary formulation auxilaries.

13. A combination comprising a compound defined in any of claims 1 to 3 and one or more pesticides selected from fludioxonil, penthiopyrad, prothioconazole, flutriafol, azoxystrobin, cyproconazole, cyprodinil, diniconazole, difenoconazole, fludioxonil, fluoxastrobin, trifloxystrobin, metalaxyl, metalaxyl-M (mefenoxam), fluquinconazole, fenarimol, nuarimol, pyrifenox, thiabendazole, tebuconazole, triadimenol, benalaxyl, benalaxyl-M, benomyl, carbendazim, carboxin, flutolanil, fuberidazole, guazatin, ipconazole, iprodione, pencycuron, propamocarb, silthiofam, thiram, triazoxide, triticonazole, a manganese compound (such as mancozeb, maneb), bitertanol, captan, imazalil, metconazole, prochloraz, prothioconazole, pyraclostrobin, triticonazole, tetraconazole, tolylfluanid, boscalid, myclobutanil, Fluopyram, a compound of formula A 71173FF

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or a tautomer of such a compound or any of its stereoisomers, thiamethoxam, imidacloprid, clothianidin, lamda-cyhalothrin, tefluthrin, β-cyfluthrin, permethrin, abamectin, fipronil, spinosad, flubendamide and a compound of formula A-1

and optionally one or more customary formulation auxiliaries.

14. A plant propagation material treated with a compound defined in any one of claims 1 to 3 or a combination defined in claim 13.

15. A method of protecting a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time against pathogenic damage or pest damage by applying to the plant propagation material a combination as defined in claim 13.

16. A method of protecting a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time against snow mold by applying to the plant propagation material a compound defined in any one of claims 1 -3 or a combination as defined in claim 13.

17. The method according to claim 16 wherein the plant is a cereal crop.