MX2008010178A - Fungicidal compositions - Google Patents

Abstract

A composition suitable for control of diseases caused by phytopathogens comprising (A) a compound of formula (I) or a tautomer of such a compound;and component (B) and component (C) are pesticides as described in claim 1.

Description

FUNGICIDAL COMPOSITIONS DESCRIPTION OF THE INVENTION The present invention relates to novel fungicidal compositions suitable for the control of diseases caused by phytopathogens, especially fungi, is related to a method for controlling diseases in useful plants and to a method for protecting storage products. It is known that certain o-cyclopropylcarboxanilide derivatives have biological activity against phytopathogenic fungi, e.g., they are known from O 03/74491. On the other hand different fungicidal compounds of different chemical classes and some mixtures of these are widely known as plant fungicides for applications in different crops of cultivated plants. However, crop tolerance and activity against phytopathogenic fungi does not always meet the needs of agricultural practice in different incidents and aspects. Apart from the aforementioned need for agricultural practice to increase crop tolerance and / or higher activity against phytopathogenic fungi, it is therefore proposed according to the present invention a novel composition suitable for the control of diseases caused by the phytopathogens that comprise Ref .: 195364 (A) a compound of formula I or a tautomer of this compound; (B) a fungicide selected from the group consisting of fludioxonil (368), metalaxyl (516), mefenoxam (517), cyprodinil (208), azoxystrobin (47), tebuconazole (761), diphenoconazole (247) and thiabendazole (790); and (C) a compound selected from the group consisting of an azole fungicide; an anilino-pyrimidine fungicide; a fungicide strobilurin; an acylalanine fungicide; fungicide benzimidazole; a fungicide selected from the group consisting of siltiofam (729), furametpir (411) and pentiopyrad; and an insecticide selected from the group consisting of abamectin (1), clothianidin (165), cyromazine (209), diafentiuron (226), diazinon (227), emamectin benzoate (291), phenoxycarb (340), fosthiazate (408) , imidacloprid (548), lambda-cyhalothrin (198), lufenuron (490), metidation (529), methiocarb (530), profenofos (662), pymetrozine (688), spinosad (737), tefluthrin (769), thiamethoxam ( 792), thiodicarb (799), a compound of formula C-1 and a compound of formula C-2 wherein (B) and (C) are different compounds. It has been found that the use of the compound (B) and the compound (C) in combination with the component (A) surprisingly and substantially improves the effectiveness of the latter against fungi, and vice versa. Additionally, the method of the invention is effective against a broad spectrum of these fungi that can be combated with active ingredients of this method, when used alone. Another aspect of the present invention is a method for controlling diseases in useful plants or a propagation material of these originated by phytopathogens, this comprises applying to the useful plants, a composition in the locus of these or the propagation material thereof according to the invention. A preferred method for controlling diseases in useful plants or in the propagation material caused by phytopathogens, which comprises applying a composition to the propagation material of the plants useful according to the invention. The compounds of formula I and their manufacturing processes starting with commercially available and known compounds are described in WO 03/074491. The compound of formula I has two chiral centers (highlighted with asterisks): and it occurs in four different stereoisomers: two trans isomers and two cis isomers ("trans" and "cis" are used to characterize the stereochemistry in the cyclopropyl ring which binds directly to the phenyl radical). The invention encompasses compositions comprising all of these stereoisomers and mixtures of these with any ratio. A preferred embodiment of the present invention is represents for those compositions comprising a component A) the trans isomer of the compounds of formula I, preferably in racemic form. Another preferred embodiment of the present invention is represented by those compositions comprising as component A) the cis isomer of the compound of formula I, preferably in racemic form. Another preferred embodiment of the present invention is represented by those compositions comprising as component A) the mixture of the racemic trans isomeric and cis isomeric isomers, with a trans / cis ratio from 1: 1 to 100: 1, for example 1: 1 , 2: 1, 3: 1, 4: 1, 5: 1, 6: 1, 7: 1, 8: 1, 9: 1, 10: 1, 20: 1, 50: 1, 100: 1. More preference is given to relate from 2: 1 to 100: 1, even more preferably from 4: 1 to 10: 1. The components (B) and the components (C) are known. Where components (B) and components (C) are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C.D.S. Tomlin; The British Crop Protection Council], are described herein under the integer given in parentheses hereinabove for the particular component (B) or the component (C); for example, the compound "abamectin" is described under the integer (1). The majority of the components (B) and the components (C) refer to the formerly so-called "common name" above. The following components (C) are registered under a CAS-Reg. No .: Penthiopyrad (CAS 183675- 82-3); Orysastrobin (CAS 248593-16-0). The compound of formula B-1 is described in EP-0-936-213 and is also known as Enestrobin. The compound of formula C-1 is described in WO-03/015519. The compound of formula C-2 is described in EP-1-610-107-A2, registered under CAS-272451-65-7 and also known as Flubendiamide. Examples of compounds especially suitable as component (C) are the compounds selected from the following group P: Group P: compounds especially suitable as component (C) in the compositions according to the invention: an azole fungicide selected from the group consisting of azaconazole (40), brumoconazole (96), ciproconazole (207), difenoconazole (247), diniconazole (267), diniconazole-M (267), epoxiconazole (298), fenbuconazole (329), fluquinonazole (385), flusilazole (393), flutriafol (397), hexaconazole (435), imazalil (449), imibenconazole (457) ), ipconazole (468), metconazole (525), myclobutanil (564), oxpoconazole (607) pefurazoate (618), penconazole (619), prochloraz (659), propiconazole (675), protioconazole (685), simeconazole (731) , tebuconazole (761), tetraconazole (778), tridimefon (814), triadimenol (815), triflumizole (834) triticonazole (842), diclobutrazol (1068), etaconazole (1129), furconazole (1198), furconazole-cis (1199) ) and quinconazole (1378); An anilino-pyrimidine fungicide is selected from the group consisting of cyprodinil (208), mepanipyrim (508) and pyrimethanil (705); a strobilurin fungicide is selected from the group consisting of azoxyestrobin (47), dimoxiestrobin (226), fluoxaestrobin (382), cresoxim-methyl (485), methominoestrobin (551), orisastrobin, picoxiestrobin (647), pyraclostrobin (690), trifloxystrobin (832) and a compound of formula B-1 an acylalanine fungicide is selected from the group consisting of benalaxyl (56); benalaxyl-R; furalaxyl (410); metalaxyl (516) and mefenoxam (Metalaxyl-M) (517); a benzimidazole fungicide is selected from the group consisting of benomyl (62) cardebndazim (116); fuberidazole (419) and thiabendazole (790); a fungicide selected from the group consisting of siltiofam, furametpir and pentiopyrad; and an insecticide selected from the group consisting of abamectin; Clothianidin; cyromazine; diafentiuron; diazinon; Emamectin benzoate; phenoxycarb; Fostiazate; imidacloprid; lambda-cyhalothrin; lufenuron; metidation; methiocarb; profenofos; pymetrozine; thorny tefluthrin; thiamethoxam; thiodicarb; a compound of formula C-1 and a compound of formula C-2. The following compositions are preferred: A composition comprising (A) a compound of formula (I), (B) fludioxonil and (C) a compound selected from group P. A composition comprising (A) a compound of formula (I), (B) metalaxyl and (C) a compound selected from group P. A composition comprising (A) a compound of formula (I), (B) medenoxam and (C) a compound selected from group P. A composition comprising (A) a compound of formula (I), (B) cyprodinil and (C) a compound selected from the group P. A composition comprising (A) a compound of formula (I), (B) azoxyestrobin and (C) a compound selected from group P. A composition comprising (A) a compound of formula (I) ), (B) tebuconazole and (C) a compound selected from group P. A composition comprising (A) a compound of formula (I), (B) difenoconazole and (C) a compound selected from the group P.

A composition comprising (A) a compound of formula (I), (B) thiabendazole and (C) a compound selected from group P. A composition comprising (A) a compound of formula (I), (B) fludioxonil and (C) a compound selected from group P. An example of a preferred composition is a composition comprising (A) a compound of formula (I), (B) fludioxonil and (C) the first compound selected from group P, which is the azaconazole compound. More preferred are compositions comprising as component (B) fludioxonil and as component (C) an azole fungicide, a strobilurin fungicide, an acylalanine fungicide or a benzimidazole fungicide. Within the compositions, the preferred component (C) is difenoconazole, mefenoxam, or thiamethoxam; even more preferably difenoconazole or mefenoxam. More preferred are compositions comprising as component (B) mefenoxam or metalaxyl and as component (C) an azole fungicide, a strobilurin fungicide, an acylalanine fungicide or a benzimidazole fungicide. Within the compositions, the preferred component (C) is difenoconazole, azoxyestrobin, tebuconazole or thiabendazole; even more preferably difenoconazole or tebuconazole. Another embodiment of the invention is represented by those mixtures comprising as component (B) cyprodinil, azoxyestrobin, tebuconazole, difenoconazole or thiabendazole. Throughout this document the expression "composition" represents the different mixtures or combinations of the component (A), component (B) and component (C), for example in a simple form "already mixed", in a spray mixture composed of the separate formulations of the components of active simple ingredients, such as "tank-mix" and in a combined use of the simple active ingredients when applied sequentially, i.e., one after the other with a reasonably short period, such as a few hours or days. The order of application of the component (A), component (B) and component (C) is not essential to work the present invention. The compositions according to the invention may also comprise one or more additional pesticides. An example of a composition according to the invention is a composition comprising a compound of formula I, fludioxonil, mefenoxam and cyprodinil, or a composition comprising a compound of formula I, fludioxonil, mefenoxam, cyprodinil and thiamethoxam, or a composition that comprises a compound of formula I, fludioxonil, mefenoxam and difenoconazole, or a composition comprising a compound of formula I, fludioxonil, mefenoxam and azoxyestrobin, or a composition comprising a compound of formula I, fludioxonil, mefenoxam, azoxyestrobin, and thiabendazole, or a composition comprising a compound of formula I, fludioxonil, mefenoxam and thiabendazole, or a composition comprising a compound of formula I, fludioxonil, mefenoxam , and thiamethoxam, or a composition comprising a compound of formula I, fludioxonil, mefenoxam, and tefluthrin, or a composition comprising a compound of formula I, fludioxonil, difenoconazole, and thiamethoxam, or a composition comprising a compound of formula I , fludioxonil, difenoconazole, and tefluthrin, or a composition comprising a compound of formula I, mefenoxam, thiabendazole, and azoxyestrobin, or A composition comprising a compound of formula I, mefenoxam, diphenaconazole, and thiamethoxam, or a composition comprising a composed of formula I, mefenoxam, difenoconazole, and tefluthrin, or a composition comprising a compound of formula I, mefenoxa m, thiabendazole, and tefluthrin. The compositions according to the invention are effective against harmful microorganisms such as fungi and phytopathogenic bacteria; preferably the microorganisms are phytopathogenic fungi. The combinations of active ingredients are effective especially against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g., Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (eg, the genera Hemileia, Rhizoctonia, Puccinnia, Ustilago, Tilletia), Fungi imperfecti (also known as Deuteromycetes, eg, Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and Pseudocercosporella herpotrichoides); Oomycetes (Phytophthora, Peronospora, Pseudopernospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara). In accordance with the invention "useful plants" typically comprise the following plant species; cereals, such as wheat, barley, rye or oats; beets such as sugar beet or beet, fruits such as pome, stone fruits or berries, for example apples, pears, peaches, apricots, almonds, cherries, strawberries, raspberries, blackberries, leguminous plants, such as beans, lentils, peas or soybeans; oil plants, such as rapeseed, mustard, poppy, olives, sunflowers, castor oil plants, cocoa beans, or peanuts; cucumber plants, such as courgettes, cucumbers or melons; fibrous plants, such as cotton, linen, hemp or jute; citrus fruits, such as oranges, lemons, grapefruits, or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, pumpkins, paprika, lauraceae, such as avocado, cinnamon, or camphor; corn; tobacco; nuts; coffee, sugar cane; tea; wines; hops; durian; bananas natural rubber plants; lawn or ornamentals, such as flowers, shrubs, broadleaved or perennial trees, for example conifers. This list does not represent any limitations. The term "useful plants" will be understood to include useful plants that have been tolerant to herbicides such as bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifluxysulfuron, EPSPS inhibitor ( 5-enol-propyl-shikimate-3-phosphate synthase), inhibitors of GS (glutamine synthase) or inhibitors of PPO (protoporphyrinogen oxidase)) as a result of conventional methods of breeding or genetic reproduction. Clearfield® summer rape (Cañóla) is an example of a culture that has been tolerant to imidazolinones, eg, imazamox, by conventional breeding methods (mutagenesis). Examples of crops that have been tolerant to herbicides or classes of herbicides by genetic design methods include corn varieties resistant to glyphosate- and glufosinate- commercially available under the trademarks RoundupReady®, Herculex | I® and LibertyLink®. The term "useful plants" is understood to also include plants that have been transformed by the use of recombinant DNA techniques that are capable of synthesizing one or more toxins that act selectively, as is known, for example, from toxin-producing bacteria, especially those of the genus Bacillus. The term "useful plants" is understood to also include useful plants that have thus been transformed by the use of recombinant DNA techniques which are capable of synthesizing anti-pathogenic substances having a selective action, such as, for example, so-called " proteins related to pathogenesis "(PRPs for its acronym in English, eg, EP-A-0 392 225). Examples of these anti-pathogenic substances and transgenic plants capable of synthesizing these antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191. The production methods of these transgenic plants are generally known to persons skilled in the art and are described, for example, in the publications mentioned above. The term "locus" of a useful plant as used herein is intended to encompass the place where the useful plants grow, where the propagation materials of the plant of the useful plants are sown or where the propagation materials of the plant the useful plants will be placed on the ground. An example of this place is a field, where the crops of the plants grow. The term "plant propagation material" is understood to denote general parts of the plant, such as seeds, which can be used for the multiplication of the latter, the plant material, such as pruning or tubers, for example potatoes. Mention may be made, for example, of seeds (in the strict sense, roots, fruits, tubers, bulbs, rhizomes and parts of plants.) Germinated plants and young plants which are transplanted after germination or after they sprout from the soil may also be mentioned. These tender plants can be protected before transplantation by a total or partial immersion treatment Preferably the "plant propagation material" is understood to denote the seeds The compositions of the present invention can also be used in the field of protection storage products against the attack of fungi According to the present invention, the term "storage products" is understood to denote natural substances of plants and / or animals and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired Storage products of plant origin, such as plants or part s of these, for example, stems, leaves, tubers, seeds, fruits or grains, can be protected in a state of fresh harvest or in processed form, such as previously dried, moistened, crushed, ground, pressed or toasted. It also falls under the definition of storage products trees for wood, if raw wood, such such as construction timbers, electricity pylons and barriers, or in the form of finished items, such as furniture or objects made of wood. The storage products of animal origin are skins, skin, fur, hairs and the like. The compositions according to the present invention can prevent disadvantageous effects such as decay, discoloration or mildew. Preferably "storage products" is understood to denote natural substances of vegetable origin and / or processed forms, more preferably fruits or their processed forms, such as knobs, stone fruits, berries fruits and citrus fruits and their processed forms. In another preferred embodiment of the invention "storage products" is meant to denote wood.

Therefore another aspect of the present invention is a method for protecting storage products, which comprises applying to the storage products a composition according to the invention. The compositions of the present invention can also be used in the field for the protection of technical material against fungal attack. In accordance with the present invention, the term, "technical material" includes, paper; carpets, constructions, cooling or heating systems; panels; ventilation and air conditioning systems and the like; preferably, "technical material" is understood to denote panels. The compositions of According to the present invention, they can prevent disadvantageous effects such as decay, discoloration or mold. The compositions according to the present invention are particularly effective against diseases of birth by seed and birth in the soil, such as blue molds, Alternaria spp., Ascochyta spp., Aspergillus spp., Penicillium spp., Botrytis cinerea, Cercospora spp. , Claviceps purpurea, Cochliobolus sativus, Colletotricum spp., Diplodia Maydis, Epicoccum spp., Fusarium culmorum, Fusarium graminearum, Fusarium monoliforme, Fusarium oxysporum, Fusarium proliferatum, Fusarium solani, Fusarium subglutinans, Gaumannomyces graminis, Helminthosporium spp., Microdochium nivale, Phoma spp., Phytophthara spp., Plasmopara spp., Pyrenophora grass, Pyricularia oryzae, Pythium spp., Rhizoctonia solani, Rhizoctonia cereals, Sclerotinia spp., Septoria spp., Sphacelotheca reilliana, Thielaviopsis basiloca, Tilletia spp., Typhula incarnata, and Urocystis occulta, Ustilago spp., or Verticillium spp. The compositions according to the present invention are in particular effective against cereal pathogens, such as wheat, barley, rye or oats; corn; rice; cotton; soybean seed; grass; beet; rapeseed with oily seed, potatoes; legumes, such as peas, lentils or chickpeas; and sunflowers. The compositions according to the present invention are more effective particularly against molds; molds blue; species that stain the leaves; early blight; molds and post-harvest diseases and molds; especially against Piccinia in cereals; Phakopsora in soybeans; Hemileia in the cafe; Phragmidium in roses; Alternating in potatoes, tomatoes and cucurbits; Sclerotinia in vegetables, sunflower and rape seed; black rot of the root, red fire, powdery mildew, gray mold, and necrosis disease in the vine; Botrytis cinerea in fruits; Monilinia spp., In fruits and Penicillium spp., In fruits. The compositions of the present invention are of particular interest to control a large amount of fungi in different plants or their seeds, especially in field crops such as potatoes, tobacco, and sugar beets, and wheat, rye, barley, oats, rice, corn , lawns, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, sugarcane, fruits and ornaments in horticulture and viticulture, in vegetables such as cucumber, beans and cucurbits. The compositions according to the invention are particularly useful for controlling the following plant diseases: Alternaria species in fruits and vegetables; Ascochyta species in legumes; Botrytis cinerea (gray mold) in strawberries, tomatoes, sunflowers and grapes; Cercospora arachidicola in peanuts; Cochliobolus sativus in cereals; Species of Colletotrichum in legumes; Erysiphe cichracearum and Sphaerotheca fuliginea in cucurbits; Erysiphe graminis in cereals; Fusarium graminearum in cereals and corn; Fusarium culmuron in cereals; Fusarium spp., In cotton, soybeans, and potatoes; Fusarium moniliforme in corn; Fusarium proliferatum in corn; Fusarium subglutinans in corn; Fusarium oxysporum in corn; Gáumannomyces graminis in cereals and lawns; Giberella fujikuroi in rice; Helminthosporium maydis in corn; Helminthosporium oryzae in rice; Helminthosporium solani in potatoes; Hemileia vastetrix in coffee; Microdochium nivale in wheat and rye; Mycosphaerella pinoides in peas; Phakopsora pachyrhizi in soybean seed; Puccinia species in cereals; Phragmidium mucronatum in roses; Phoma spp., In sugar beets; Phoma exigua in potatoes; pythium spp., in cereals, cotton, corn and soybeans; Plasmopara halstedii in sunflowers; Pyrenophora grminea in barley; Pyricularia oryzae in rice; Rhizoctonia species in cotton, soybeans, cereals, corn, potatoes, rice and turfgrass; Sclerotinia homeocarpaen lawns; Septoria spp., In cereals; Sphacelotheca reilliana in corn; Tilletia species in cereals; Typhula incarnata in barley; Uncicula necátor, Guignardia bidwelli and Phomopsis vitícola in wines; Urocystis occulata in rye; Ustilago species in cereals and corn; Fruit monilinia in stone fruits; Monilinia fructigena in fruits; Monilia laxa in stone fruits; Penicillium digitatum in citrus fruits; Penicillium expansum in apples; and Penicillium italicum or citrus.

The compositions according to the invention are valuable preventive and / or curative ingredients in the field of pest control, even at low application rates, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. Some of the active ingredients according to the invention are known for their insecticidal action against stages of total or individual development normally sensitive, but also resistant, animal pests, as insects or representatives of the Acariña order. The insecticidal or acaricidal activity of the compositions according to the invention, which comprises the active ingredients, can be manifested directly, that is, in the destruction of the pests that is carried out either immediately or only after some time has passed, for example during the ecdysis, or indirectly, for example in a reduced oviposition and / or incubation ratio, a good activity corresponding to a destruction ratio (mortality) of at least 50 to 60%.

Examples of the animal pests mentioned above are: of the order Acariña, for example, Acarus siró, Sheldoni mill, Aculus Schlechtendali, Amblyomma spp., Argas spp., Boophilus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus carpini, Eriophyes spp., Hyalomma spp., Ixodes spp. , Oligonychus prantensis, Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Tarsonemus spp., Tetranychus spp .; from the order of Anoplura, for example, Haemotopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., and Phylloxera spp .; of the order Coleoptera, for example, Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa decemlineata, Lissorhoptrus spp. ., Melolantha spp., Orycaephilus spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylloides spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Triblolium spp., And Trogoderma. spp .; of the order Diptera, for example, Aedes spp., antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp. , Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia Hyoscyami, Phormia spp., Rhagoletis pomonella, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp., and Typula spp .; of the order Heteroptera, for example, Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp., Eurygaster spp., Leptocorisa spp., Nexara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp., and Triatoma spp .; of the order Homoptera, for example, Aleurothriux floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Bemisa tobacco, Ceroplaster spp., Chrysomphalus aonidium, Chrysompalus dictyospermi, Coccus hesperidium, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp., Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Parlatoria spp., Pemphigus spp., Planococus spp., Pseudaulacaspis spp. , Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobio spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri; on the order of Hymenoptera, for example, Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp., and Vespa spp. , of the order Isoptera, for example, Reticulitermes spp .; of the order Lepidoptera, for example, Acléris 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, Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydia spp., Diatrea spp., Diparopsis castanea, Earias spp. , Ephestia spp., Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria spp. , Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Operophtera spp. , Ostrinia nubialis, Pammene spp., Pandemis spp., Panolis spp., Panolis flammea, Pectinophora gossypiela, Phthorimaea, operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp. ., Spodeptera spp., Synanthedon spp. , Thaumetopoea spp., Tortrix spp., Trichoplusia ni and Yponomeuta spp .; of the order Mellophaga, for example Damalinea spp., and Trichodectes spp .; of the order Orthoptera, for example, Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp., and Schistocerca spp .; of the order Psocoptera, for example, Liposcelis spp .; of the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp., and Xenopsylla cheopis; of the order Thysanoptera, for example, Frankliniella spp., Hercinothrips spp., Scirtothrips aurantii, Taeniothrips spp., Thrips palmi and Thrips tabaci; of the order Thysanura, for example, Lepisma saccharina; Nematodes, for example root nematodes, stem eel and leaf nematodes; especially Heterodera spp., for example Heterodera schachtii, Heterodora avenae and Heterodora trifolii; Globodera spp., For example globodera rostochiensis; Meloidogyne spp., For example Meloidogyne incoginita and Meloidogyne javanica; Radopholus spp., For example Radopholus similis; Pratylenchus, for example Pratylenchus neglectans and Pratylenchus penetrans; Tylenchulus, for example Tylenchulus semipenetrans; Longidorus, Trichodorus, Xiphinema, Ditylenchus, Aphelenchoides and Anguina; aphid beetle (Phyllotreta spp.); root worms (Delia spp.); and ceutorrincos of the turnips (Ceutorhynchus spp.). These compositions according to the invention can be used to control, that is, contain or destroy pests of animals of the type mentioned above that occur in useful plants in agriculture, in horticulture and in forests, or in organs of useful plants, such as fruits, flowers, foliage, stems, tubers or roots and in some cases of useful plants that are formed at the last point of time that remain protected against these pests. animals. In general, the weight ratio of compound (A) to compound (B), the weight ratio of compound (A) to compound (C) and the weight ratio of compound (B) to compound (C) is from 1000 : 1 to 1: 1000. A non-limiting example for these weight ratios is a composition, wherein the weight ratio of the compound of formula (I): fludioxonil: difenoconazole is 10: 1: 1. In this example the weight ratio of the compound of formula (I): fludioxonil, ie (A: B), is 10: 1, the weight ratio of the compound of formula (I): difenoconazole, ie (A: C ), it's 10: 1; and the weight ratio of the fludioxonil compound: diphenoconazole, ie (B :), is 1: 1. In one embodiment of the invention, component (C) is a fungicide. In this embodiment of the invention, the weight ratio of (A) to (B), from (A) to (C) and from (B) to (C) is preferably from 100: 1 to 1: 100; more preferably from 20: 1 to 1:20; and even more preferably from 10: 1 to 1:10. In another embodiment of the invention, component (C) is an insecticide. In this embodiment of the invention, the weight ratio of (A) to (B), from (A) to (C) and from (B) to (C) is preferably from 400: 1 to 1: 400. More preferably in the embodiment of the invention, the weight ratio of (A) to (B), and from (A) to (C) is from 100: 1 to 1: 100; and the weight ratio of (B) to (C) is from 100: 1 to 1: 400. Even more preferably the weight ratio of (A) to (B) is from 20: 1 to 1:20; From aa (C) is from 20: 1 to 1: 100 and from (B) to (C) is from 20: 1 to 1: 400. Even more preferably, the weight ratio of (A) to (B) is from 10: 1 to 1:10; from (A) to (C) is from 10: 1 to 1:80 and from (B) to (C) is from 20: 1 to 1: 400. In one embodiment of the invention, wherein component (C) is an insecticide, the weight ratio of (A) to (B) is from 10: 1 to 1: 5; From aa (C) is from 20: 1 to 1:20 and from (B) to (C) is from 1: 1 to 1: 100.

It has surprisingly been found that certain weight ratios of component (A) with the combination of components (B) and (C) are capable of providing an increase in synergistic activity. Therefore, another aspect of the invention is the compositions, wherein component (A), component (B) and component (C) are present in amounts that produce a synergistic effect. This synergistic activity is apparent from the fact that the fungicidal activity of the composition comprising the component (A), component (B) and component (C) is greater than the sum of the fungicidal activities of the component (A) and the components (B) and (C) combined. This synergistic activity extends in the range of action of component (A), component (B) and component (C), in two ways. First, the application ratios of component (A), component (B) and component (C) are lower while the action remains equally good, meaning that the mixture of active ingredients still achieves a high degree of control of phytopathogens even where all three Individual components have been totally inefficient with a low range of their application ratio. Second, there is a substantial expansion of the spectrum of phytopathogens that can be controlled. However, despite the current synergistic action with respect to the fungicidal activity, the compositions according to the invention may also have other surprising advantageous properties. Examples of these advantageous properties that may be mentioned are: greater advantageous degradation; toxicological improvement and / or exotoxicological behavior; or improved characteristics of useful plants including: emergence, harvest yields, more developed root systems, increased tillering, increased plant height, greater limb, lower death of basal leaves, larger shoots, leaf color more green, less need for fertilizers, less need for - seeds, more productive shoots, early flowering, early maturing of the grain, lower return of the plant (bedding), increased rod growth, improved plant vigor, and early germination. The compositions according to the invention have a systemic action and can be used as fungicides for the foliar, soil and seed treatment. With the compositions according to the invention it is possible to inhibit or destroy phytopathogenic microorganisms that occur in plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots) in different useful plants, while at the same time the parts of plants that grow late are also protected from attack by phytopathogenic microorganisms. The compositions according to the invention can be applied to microorganisms, useful plants, their locus, propagation material thereof, storage products or technical materials treated against the attack of microorganisms. The compositions according to the invention can be applied before or after the infection of the useful plants, the propagation material thereof, the storage products or technical materials by the microorganisms.

The amount of a composition according to the invention that will be applied will depend on different factors, such as the compounds used; the subject of treatment, such as, for example, plants, soil or seeds; the kind of treatment, such as, for example, spraying, pulverizing or peeling of the seed; the purpose of the treatment, such as, for example, prophylactic or therapeutic; the type of fungi that will be controlled or the application time. When applied to useful plants, compound (A) is applied at a rate of 5 to 2000 g of i. to. / Ha, particularly from 10 to 1000 g. of i. to. / Ha, eg, 50, 75, 100 or 200 g of i. to. / Ha, in association with 1 to 5000 g of i. to. / Ha, particularly from 2 to 2000 g of i. to. / Ha, eg, 100, 250, 500, 800, 1000, 1500 g of i. to. / Ha, of the compound (B) and in association with 1 to 2000 g of i. to. / Ha, particularly from 1 to 5000 g of i. to. / Ha, particularly from 2 to 2000 g of i. to. / Ha, eg, 100, 250, 500, 800, 1000, 1500 g of i. to. / Ha, of the compound (C). In agricultural practice the application ratios of the compositions according to the invention depend on the type of effect desired, and usually the range is from 7 to 12000 g of the total composition per hectare, more preferably from 20 to 4000 g of total composition per hectare. In one embodiment of the invention, component (C) is a fungicide. In this embodiment, when the compositions according to the invention are used to treat seeds, the ratios of 0.5 to 100 g of the component (A) per 100 Kg of seed, preferably from 2.5 to 40 g per 100 Kg of seed, more preferably 5 to 10 g per 100 kg of seed, and 0.01 to 200 g of component (B) per 100 kg of seed, preferably from 0.1 to 50 g per 100 kg of seed, more preferably 1 to 20 g per 100 Kg of seed, and 0.01 to 200 g of component (C) per 100 Kg of seed, preferably from 0.1 to 50 g per 100 Kg of seed, more preferably from 1 to 20 g per 100 Kg of seed are generally sufficient . In another embodiment of the invention, component (C) is an insecticide. In this embodiment, when the compositions according to the invention are used to treat the seeds, the components (A) and (B). they are usually applied with ratios as described above, while component (C) is applied at ratios of 0.01 to 2000 g per 100 kg of seed, preferably from 0.1 to 1000 g per 100 kg of seed, more preferably 1 to 400 g per 100 Kg of seed. The composition of the invention can be used in any conventional manner, for example in the form of a double pack, a powder treatment for dry seed (DS), an emulsion for treatment of the seed (ES), a concentrate that can flow for the seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for the treatment of the seed (S), a suspension in capsule for the treatment of the seed seed (CF), a gel for seed treatment (GF), an emulsion centering (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), granules water dispersible (WG), an emulsifying granule (EG), an emulsion, water in oil (EO), an oil-in-water emulsion (EW), a micro-emulsion (ME), or a dispersion (OD), an oil miscible that can flow (OF), an oil miscible liquid (OL), a soluble concentrate (SL), a suspension with ultra low volume (SU), a liquid with ultra low volume (UL), a technical concentrate (TK) , a dispersible concentrate (DC), a moistenable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants. These compositions can be produced in conventional manner, eg, by mixing the active ingredients with appropriate inert formulation adjuvants (diluents, solvents, fillers, and optionally other formulation ingredients such as surfactants, biocides, antifreezes, adhesive, thickener and compounds that they provide adjuvant effects). Conventional slow release formulations can also be used where long-term efficacy is projected. Particularly the formulations that will be applied in spray forms, such as water dispersible concentrate (eg, EC, SC, DC, OD, SE, EW, EO and the like), powders and granules that can be wetted, can contain surfactants, such as wetting and dispersing agents and other compounds that provide adjuvant effects, eg, the condensation product of formaldehyde with naphthalene sulfonate, an alkyl arylsulfonate, a lignin sulfonate, a fatty alkyl sulfate, and Ethoxylated alkylphenol and an ethoxylated fatty alcohol. A seed-covering formulation is applied in a manner known per se to seeds using the compositions according to the invention and a diluent in the form of a suitable seed-covering formulation, eg, an aqueous suspension or in the form of a suspension. powder that has good adherence to the seeds. These formulations covering the seeds are known in the art. The formulations that cover the seed contain the simple active ingredients or the combination of the active ingredients in encapsulated form, eg, as capsules or microcapsules of delayed release. In general, the formulations include from 0.01 to 90% by weight of the active agent, from 0 to 20% of the agriculturally acceptable surfactant and 10 to 99.99% of inerts of the solid or liquid formulation and adjuvant (s), the active agent consists of less of component (A) together with component (B) and together with component (C), and optionally other active agents, particularly microbicides or preservatives or the like. The concentrated forms of the compositions they generally contain between about 2 and 80%, preferably between about 5 and 70% by weight of the active agent. The application forms for example may contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of the active agent. While commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.

The following Examples serve to illustrate the invention, "active ingredient", denoting a mixture of component (A), component (B) and component (C) with a specific mixing ratio.

Formulation examples Wettable powders a) b) c) Active ingredient [A): B): C) = 25% 50% 75% l: 3: 3 (a), l: 2: 2 (b), l: l : l (c)] Sodium lignosulfonate 5% 5% Sodium lauryl sulfate 3% - 5% Diisobutylnaphthalenesulfonate - 6% 10% sodium Phenol polyethylene glycol ether - 2% (7-8 moles of ethylene oxide) Highly dispersed silicic acid 5 % 10% 10% Kaolin 62% 27% The active ingredient is mixed thoroughly with the adjuvants and the mixture is completely milled in a suitable mill, producing wettable powders, which can be diluted with water to give the suspensions at the desired concentration.

Powders for dry treatment a) b) c) 'of the seeds Active ingredient [A): B): C) = 25% 50% 75% l: 3: 3 (a), l: 2: 2 (b), l: l: l (c)] Light mineral oil 5% 5% Highly dispersed silicic acid 5% 5% Kaolin 65% 40% Talc - 20% The active ingredient is completely mixed with the adjuvants and the mixture is completely milled in a suitable mill, producing powders that can be used directly for the treatment of the seeds.

Emulsifying concentrate Active ingredient (A): (B): (C) = 1: 6: 6 10% Octylphenol polyethylene glycol ether 3% (4-5 moles of ethylene oxide) 3% calcium dodecylbenzenesulfonate Castor oil polyglycol ether 4% (35 moles of ethylene oxide) Cyclohexanone 30% Mixture of xylene 50% Emulsions of any required dilution can be used in the protection of plants, this concentrate can be obtained by dilution with water.

Powders a) b) c) Active ingredient [A): B): C) = 5% 6% 4% l: 6: 6 (a), l: 2: 2 (b), l: 10: 10 (c )] Talcum 95% Kaolin - 94% Mineral filler - - 96% The ready-to-use powders are obtained by mixing the active ingredient with the carrier and milling the mixture in a suitable mill. These powders can also be used to dry-coat the seeds.

Extruder granules Active ingredient A): B): C) = 2: 1: 1) 15% Sodium lignosulfonate 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 A): B): C) = 1:10:10) 8% Polyethylene glycol (mol Weight 200) 3% Kaolin 89% The finely ground active ingredient is applied uniformly, in a mixer, with a kaolin moistened with polyethylene glycol. In this way, non-dusty coated granules are obtained.

Concentrate in suspension Active ingredient A): B): C) = 1: 8: 8) 40% Propylene glycol 10% Nonylphenol polyethylene glycol 6% ether (15 moles of ethylene oxide) 10% sodium lignosulfonate Carboxymethylcellulose 1% Silicone oil ( in the form of 1% an emulsion in 75% water) Water 32! The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension suspension of these suspensions any desired dilution can be obtained by dilution with water. Using these dilutions, which leaves the plant as well as the propagation material of the plant to be treated and protected against the infestation of microorganisms, by spraying, pouring or immersion.

Concentrate that can flow for the treatment of the seeds Active ingredient A): B): C) = 1: 8: 8) 40% Propylene glycol 5% Copolymer of butanol PO / EO 2% Triestirephenol with 10-20 moles of EO 2% 1, 2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5% Calcium monoazo-pigment salt 5% Silicone oil (in the form of 0.2% an emulsion in 75% water) Water 45.3% The finely ground active ingredient is mixed intimately with the adjuvants, by giving a suspension in suspension with these suspensions, any desired dilution can be obtained by dilution with water. Using these dilutions, which leaves the plant as well as the propagation material of the plant to be treated and protected against the infestation of microorganisms, by spraying, pouring or immersion.

Suspension in Delayed Release Capsule 28 parts of a combination of the compound of formula (I), a compound of component (B) and a compound of component (C), or of each of these compounds separately, are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisnate / polymethylene-polyphenylisnate mixture (8: 1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoam and 51.6 parts of water to achieve the desired particle size. To this emulsion was added a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water. The mixture was stirred until the polymerization reaction was completed. The obtained capsule suspension was stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% active ingredients. The average diameter of the capsule is 8-15 micrometers. The formulation The resultant is applied to the seeds as an aqueous suspension in a device suitable for this purpose.

Biological Examples Compared to a mixture of two active ingredient compounds, such as, for example (B + C), the action that will be expected (additive action) E for a combination of active ingredients of three compounds (A + B + C) ) can be calculated as follows (COLBY, SR "Calculating the synergy and antagonistic responses of the herbicide combination." eeds, Vol. 15, pages 20-22, 1967): ppm = milligrams of active ingredient (= ia) per liter of sprayed mixture XBc =% action for a mixture (B + C), for example, using p ppm of the active ingredient. Z =% action for the active ingredient A) using r ppm of the active ingredient.

E = XBC + [Z (100-X) / 100] In this way, if the action observed for the given combination of the three active ingredients (A + B + C) is greater than the action expected by the Colby formula, then synergism occurs. The synergistic effect of the compositions of the present invention is demonstrated in the following Examples. If the current action (O) is observed, it is greater than the expected action (E), then the action of the combination is unique, that is, it is a synergistic effect. In mathematical terms, the synergism corresponds to a positive value for the difference of (O-E). In the case of the purely complementary addition of the activities (expected activity), the difference (O-E) is zero. A negative value of the difference (O-E) indicates a loss of activity compared to the expected activity.

Example B-1: Activity against Pyrenophora grass The conidium of the cryogenic storage fungi was directly mixed in a nutrient broth (potato dextrose broth PDB). After placing a solution (DMSO) of the test compounds in a microtiter plate (96 well format) the nutrient broth containing the fungal spores is added. Test plates were incubated at 24 ° C and growth inhibition was measured photomatically after 72 hours. The fungicidal interactions in the combinations were calculated according to the COLBY method.

Compound A as used in examples B-1 to B-5 have been trans-isomer of the compound of formula I in racemic form.

Example B-2: Activity against Gaumannomyces graminis Mycelial fragments of a new growing culture of fungi, was mixed directly into the nutrient broth (PDB dextrose broth PDB). By placing a solution of (DMSO) of the test compounds in a microtiter plate (96-well format) the nutrient broth was added with the fungal spores. The test plates were incubated at 24 ° C and growth inhibition was determined photometrically after 72 hours. The fungicidal interactions in the combinations were calculated according to the COLBY method.

Example B-2: Activity against Rhizoctonia solani Mycelial fragments of fungi from cryogenic storage was mixed directly into the nutrient broth (potato dextrose broth PDB). After placing a solution of (DMSO) of the test compounds in a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 ° C and growth inhibition was determined photometrically after 48 hours. The fungicidal interactions in the combinations were calculated according to the COLBY method.

Example B-4: Activity against Pythium ultimum Mycelial fragments of a new growth in liquid growth of the fungi, was mixed directly into the nutrient broth (potato dextrose broth PDB). By placing a solution of (DMSO) of the test compounds in a microtiter plate (96-well format) the nutrient broth containing the mycelial / fungal spore mixture was added. The test plates were incubated at 24 ° C and growth inhibition was determined photometrically after 48 hours. The fungicidal interactions in the combinations were calculated according to the COLBY method.

The conidia of the cryogenic storage fungi were directly mixed in a nutrient broth (potato dextrose broth PDB). After placing a solution (DMSO) of the test compounds in a microtiter plate (96 well format) the nutrient broth containing the fungal spores is added. The test plates were incubated at 24 ° C and the inhibition of growth was determined photometrically after 48 hours. The fungicidal interactions in the combinations were calculated according to the COLBY method.

It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (16)

1. CLAIMS Having described the invention as above, the content of the following claims is claimed as property. 1. Composition suitable for the control of diseases caused by phytopathogens, characterized in that it comprises (A) a compound of formula I or a tautomer of this compound; (B) a fungicide selected from the group consisting of fludioxonil, metalaxyl, mefenoxam, cyprodinil, azoxystrobin, tebuconazole, difenoconazole and thiabendazole; Y (C) a compound selected from the group consisting of an azole fungicide; an anilino-pyrimidine fungicide; a fungicide strobilurin; an acylalanine fungicide; fungicide benzimidazole; a fungicide selected from the group consisting of siltiofam, furametpir and pentiopyrad; and an insecticide selected from the group consisting of abamectin, clothianidin, cyromazine, diafentiuron, diazinon, emamectin benzoate, phenoxycarb, fosthiazate, imidacloprid, lambda-cyhalothrin, lufenuron, metidation, methiocarb, profenofos, pymetrozine, spinosad, tefluthrin, thiamethoxam, thiodicarb, a compound of formula C-1 and a compound of formula C-2 wherein (B) and (C) are different compounds.
2. 2. Composition according to claim 1, characterized in that (B) is fludioxonil.
3. 3. Composition according to claim 2, characterized in that (C) is an acylalanine fungicide.
4. 4. Composition according to claim 2, characterized in that (C) is difenoconazole or mefenoxam.
5. 5. Composition according to claim 1, characterized in that (B) is mefenoxam or metalaxyl.
6. 6. Composition according to claim 1, characterized in that (B) is mefenoxam.
7. Composition according to claim 6, characterized in that (C) is an azole fungicide, a strobilurin fungicide or an acylalanine fungicide.
8. Composition according to claim 6, characterized in that (C) is difenoconazole, azoxyestrobin or thiabendazole.
9. Composition according to claim 1, characterized in that the weight ratio of (A) to (B), the weight ratio of (A) to (C) and the weight ratio of (B) to (C) It is from 1000: 1 to 1: 1000.
10. 10. Method for controlling diseases in useful plants or in the propagation material of those caused by phytopathogens, characterized in that it comprises applying to the useful plants, in the locus of these or the propagation material thereof a composition according to claim 1
11. 11. Method according to claim 10, characterized in that it comprises applying to the propagation material of the plants a composition according to claim 1.
12. 12. Method for protecting storage products, characterized in that it comprises applying to the storage products a composition according to claim 1.
13. 13. Composition according to claim 1, characterized in that (B) is Fludioxonil, (C) is Mefenoxam and this composition additionally comprises Thiamethoxam.
14. 14. Composition according to claim 1, characterized in that (B) is Fludioxonil, (C) is Mefenoxam and this composition additionally comprises Thiabendazole.
15. 15. Composition according to claim 1, characterized in that (B) is Fludioxonil, (C) is Mefenoxam and this composition additionally comprises Difenoconazole.
16. 16. Method for controlling diseases in useful plants or in propagation material of these originated by phytopathogens, characterized in that it comprises applying to the useful plants, to the locus of these or to the propagation material thereof a composition according to any of the claims 13 to 15.