MXPA00004486A - Isothiazole carboxylic acid amides and the application thereof in order to protect plants - Google Patents

Abstract

The invention relates to novel isothiazole carboxylic acid amides of formula (I) in which R has the meanings given in the description. The invention also relates to additional methods for producing the novel materials and the application thereof in order to protect plants against attack by undesired microorganisms and animal pests.

Description

ISOTIAZOLCARBOXIAMIDAS AND ITS EMPLOYMENT FOR THE PROTECTION OF PLANTS Field of the Invention The present invention relates to new isothiazolcarboxyamides, to various processes for their preparation and to their use for the protection of plants against attack due to undesirable microorganisms and animal pests.

Background of the Invention It has already been reported that a large number of isothiazolecarboxylic acid derivatives have fungicidal properties (see US-A 5 240 951 and JP-A 06-009 313). Thus, for example, N-et i 1-3, 4-dichloro-isothiazole-5-carboxamide and 3,4,4'-t-ricloro-isothiazole-5-carboxanyl-ida for the control of fungi can be used. The activity of these products is good but leaves much to be desired, however, with low application rates.

Ref: 119570 Description of the invention New isothiazolecarboxyamides of the formula have now been found in which R means a radical of the formula .TO . where RJ means cyano, cycloalkyl phenyl with 3 to 7 carbon atoms, R means a radical of the formula where R2 means -C "(CH3) 3, -CH-C2H5, -CH-C2H5, I I C2H5 CH3 cycloalkyl with 3 to 7 carbon atoms or means - CH2-S-R3, where R stands for C 6 -alkyl, or means halogen and / or C 1 -C 6 -alkyl substituted, if appropriate, by phenyl, R means a radical of the formula where Rl means hydrogen or N, -dialkylamino with 1 4 carbon atoms R means a radical of the formula where R means hydrogen or alkoxy with 1 to 4 carbon atoms and R represents alkoxy with 1 to 4 carbon atoms, alkyl having 1 to 6 carbon atoms, phenyl optionally substituted by halogen or phenoxy means optionally substituted by halogen, R means phenoxy substituted, if appropriate, by halogen and Rc means hydrogen, R means a radical of the formula -CH2-CH2-0-R- where R7 means alkyl with 1 to 4 carbon atoms, R8 means alkyl with 1 to 4 carbon atoms and R ^ means hydrogen a radical of the formula R means a radical of the formula where R10 means halogen, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms and n means integers from 0 to 3 In addition it has been found that the isothiazolecarboxyamides of the formula (I) are obtained, if a) 3,4-dichloro-isothiazole-5-carbonyl chloride of the formula is reacted with amines of the formula H2N-R (III) in which R has the meanings indicated above, if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent, b) 3,4-dichloro isothiazole-5-carboxyamide of the formula is reacted with hydroxy compounds of the formula HO-CH2-X (V) wherein X means a radical of the formula where R4, R5, R6 and R8 have the meanings indicated above, in the presence of a diluent and in the presence of a water-dissociating agent.

Finally it has been found that the isothiazolecarboxyamides of the formula (I) can be used in a very good way for the protection of plants against attack due to undesirable microorganisms. The products according to the invention are suitable both for the mobilization of the defensive forces of plants against attack due to undesirable microorganisms and as microbicides for the direct fight against microorganisms. In addition, the products according to the invention also have an effect against plant pests.

Surprisingly, the products according to the invention have a microbicidal activity better than that of N-e t 1 -3, -dichloro-isothiazole-5-carboxamide and that of 3, 4, 4'-t ricloro- isot-iazol-5-carboxanilide, which are active products known before, similar from the point of view of their constitution, with the same direction of activity.

The isothiazolecarboxyamides according to the invention are generally defined by the formula (I). Preference is given to the compounds of the formula (I), in which R means a radical of the formula where R means cyano, phenol, cyclopentyl, cyclohexyl cycloheptyl, means a radical of the formula where R ^ means -C (CH3) 3, -CH-C2H5, -CH-C2H5, I I C2H5 CH3 cyclopentyl, cyclohexyl, cycloheptyl or means -CH2-S-R3, where R represents alkyl of 1 to 5 carbon atoms or phenyl, optionally substituted one to three times, in the same or different manner by fluorine, chlorine, bromine and / or alkyl with 1 to 4 carbon atoms , R means a radical of the formula where R means hydrogen or N, N-dialkyl-1-aminomethyl with 1 or 2 carbon atoms in each alkyl part, R means a radical of the formula where R means hydrogen or alkoxy with 1 or 2. carbon atoms and R6 means alkoxy with 1 or 2 carbon atoms, alkyl having 1 to 4 carbon atoms, phenyl optionally substituted one to three times, in the same or different way by fluorine, chlorine and / or bromine or phenoxy substituted, if appropriate, one to three times, in the same manner or in the same or different forms by fluorine, chlorine and / or bromine, or R5 means phenoxy substituted, if appropriate, one to three times, in the same or different ways by fluorine, chlorine and / or bromine and R 'means hydrogen, R means a radical of the formula • CH2-CH2-0-R9, where R 'means methyl or ethyl, RE means methyl or ethyl and R means hydrogen or a residue of the formula R means a radical of the formula where R10 means fluorine, chlorine, bromine, methyl, ethyl, methoxy ethoxy and n means integers from 0 to 3, meaning R10 equal or different radicals when n means 2 or 3.

The definitions of the abovementioned substituents can be combined with each other. Some individual definitions may also be absent.

If the 3,4-dichloro-isothiazole-5-carbonyl chloride and the 2-cyanoaniline are used as starting materials, the development of the process (a) according to the invention can be represented by means of the scheme of the following formulas: If 3, 4-dichloro-isothiazole-5-carboxyamide and N-formyl-N-hydroxymethylmethylamine are used as starting materials, the development of process (b) according to the invention can be represented by means of the formulas scheme following.

The 3-dichloro-isothiazole-5-carbonyl chloride of the formula (II), which is necessary as starting material for carrying out the process (a) according to the invention, is known (see US-A-5 240 951).

Furthermore, the amines necessary as components of the reaction for carrying out the process (a) according to the invention are defined by the formula (III). In this formula R preferably has those meanings which have already been mentioned as being preferred for these radicals in relation to the description of the products of the formula (-1 according to the invention.

The amines of the formula (III) are known or can be prepared according to methods known per se.

Suitable acid-binding agents in the process (a) according to the invention are all the usual inorganic bases. Preference is given to using hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates of alkaline earth metals or alkali metals, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butyl potassium , sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, furthermore ammonium hydroxide, ammonium acetate or ammonium carbonate or tertiary amines, as trimet ilamine, triethylamine, tributyl, N, N-dimethylanimine, NN-dimethylbenzyl sheet, pyridine, N-methypiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diabicyclooctane (DABCO), diazabicyclononene diazabicycloundecene (DBU).

Suitable diluents for carrying out process (a) according to the invention are all inert organic solvents. Preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, t et racloromethane, dichloroethane or t-ricloroethane; ethers, such as diethyl ether, diisopropyl ether, met il-t-butyl ether, methylthamyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N, N-dimethylformamide, -dimethylacet amide, N-methylformanide, N-meth i-pyrrolidone or hexamethylphosphoramide; esters such as methyl acetate or ethyl acetate; sulfoxides, such as dimethyl sulfoxide; sulfones, such as sulfolane.

The reaction temperatures in the process (a) according to the invention can vary within wide limits. In general, the process is carried out at temperatures between -10 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.

In carrying out the process (a) according to the invention, the reaction is generally carried out under atmospheric pressure. However, it is also possible to work under higher pressure or, as long as no volatile components participate in the reaction, under reduced pressure.

In carrying out the process (a) according to the invention, 1 mole of 3, 4-dichloro-isothiazole-5-carbonyl of the formula (II) is used, in general, from 1 to 5 mol, preferably from 1 to 5 mol. 1 to 2 moles of amine of the formula (III), as well as an equivalent amount or an excess of acid accepting agent. Working up is carried out by customary methods. In general, the reaction proceeds in such a way that the reaction mixture, once the conversion is completed, is concentrated by evaporation, the remaining residue is combined with water and with an organic solvent not very miscible with water, the organic phase is separated, washed, dried and concentrated by evaporation. The remaining product can be freed from the impurities optionally contained according to usual methods.

The 3,4-dichloro-isothiazole-5-carboxyamide of the formula (IV) required as starting material for carrying out the process (b) according to the invention is known (see US-A-5 240 951).

The hydroxy compounds furthermore required as components of the reaction for carrying out the process (b) according to the invention are generally defined by means of the formula X preferably means a residue of the formula -CH; -R ' where R means hydrogen or N, N-dialkyl aminomethyl with 1 or 2 carbon atoms in each alkyl part, R means hydrogen or alkoxy with 1 or 2 carbon atoms, R6 means alkoxy having 1 or 2 carbon atoms, alkyl having 1 to 4 carbon atoms, phenyl optionally substituted one to three times, the same or different forms, fluorine, chlorine and / or bromine, or means phenoxy substituted, if appropriate, one to three times, in the same or different ways by fluorine, chlorine and / or bromine.

R5 means phenoxy substituted, if appropriate, one to three times, of the same or different forms by fluorine, chlorine and bromine and Rr means hydrogen and R < means methyl or ethyl The hydroxy compounds of the formula (V) are known or can be prepared by methods known per se.

Suitable diluents for carrying out the process (b) according to the invention are all the inert organic solvents customary for this type of reaction. Preferably, glacial acetic acid can be used.

As water-dissociating agents, all the usual reagents are suitable for dehydration when carrying out process (b) according to the invention. Preference is given to using acids, such as sulfuric acid or p-toluenesulfonic acid, and also drying agents, such as anhydrous silica gel.

The reaction temperatures in the process (b) according to the invention can vary within wide limits. In general, the process is carried out at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 130 ° C.

Also in carrying out the procedure (b) according to the invention, the work is generally carried out under atmospheric pressure. However, it is also possible to work under higher pressure or at a lower pressure.

In carrying out the process (b) according to the invention, 1 mole of the 3-, 4-dichloro-isothiazole-5-carboxyamide of the formula are used (IV), in general from 1 to 2 moles, preferably from 1 to 1.5 moles of hydroxy compound of the formula (V) as well as from 2 to 6 moles of water dissociating agent. Working up is carried out by customary methods. In general, the procedure is carried out in such a way that the reaction mixture is combined with water, then it is extracted with an organic solvent that is not very miscible with water, the combined organic phases are dried and concentrated by evaporation under reduced pressure. The remaining product can be freed from the impurities present, optionally still according to customary methods.

The active compounds according to the invention have a potent plant-reinforcing effect, and are therefore suitable for mobilizing the plant's own defensive forces against attack due to undesirable micro-organisms.

By reinforced products of the plants (resistance inducers) should be understood in the present context those substances, which are capable of stimulating the defensive system of the plants in such a way that the treated plants, when a subsequent inoculation with undesirable microorganisms occurs, develop a broad resistance against these microorganisms.

Undesirable microorganisms should be understood in the present case as phytopathogenic fungi, bacteria and viruses. The products according to the invention can be used, therefore, to protect the plants, within a certain period of time, from the treatment, against the attack of said harmful pathogens. The lapse of time, in which protection takes place, extends, in general from 1 to 10 days, preferably from 1 to 7 days from the treatment of the plants with the active products.

The active compounds according to the invention have, in addition to the reinforcing effect of the plants (resistance inducer), also a potent microbicidal effect and are also used in practice for direct control against undesirable microorganisms. The active products they are suitable for use as protective agents of plants, especially as fungicides.

To the undesirable microorganisms in the protection of the plants belong fungi of the classes of plasmodioforomycetes, oomycetes, qui t ridiomycetes, zygomecetes, ascomycetes, basidiomycetes, deuteromi cetes.

By way of example, but without limitation, some pathogens of fungal diseases are mentioned, which fall within the general definitions given above: types of pitium, such as for example Pythimun ultimun; phytophthora types, such as for example Phyt ophothora infestans; pseudoperonospora types, such as, for example, Pseudoperonosopora humuli or Pseudoperonospora cubensis; types of plasmopara, such as for example Plasmopara viticola; types of peronospora, such as, for example, Peronospora pisi or P. brassicae; types of erisife, such as for example Erysiphe graminis; types of sfaeroteca, such as for example Sphaerotheca fuligínea; types of podosfaera, such as for example Podosphaera leucotricha; types of venturia, such as for example Venturia inaequa lis; Pyrenophora species, such as Pyrenophora teres' or P. Graminea (conidia form; Drechslera Synonym; Helminthosporium); types of cocliobolus, such as, for example, Cochiobolus sativus (conidia form, Drechslera, Syn: Helminthoporium); types of uromices, such as, for example, Uromyces appendiculatus; types of pucina, such as for example recondite Puccina; types of tilletia, such as for example _Tilletia caries; types of ustylago, such as, for example, Ustilago nuda or Ustilago avenae; types of pelicularia, such as, for example, Pellicularia sasakii; blasting types, such as, for example, Pyricularia oryzae; fusarium types, such as, for example, Fusarium culmorun; Botrytis types, such as, for example, Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of leptosphaeria, such as for example Leptosphaeria nodorum; types of cercospora, such as for example Cercospora canescens; alternating types, such as, for example, Alternaria brassicae; types of pseudocercosporela, such as, for example, Pseudocercosporella herpotrichoides.

The good compatibility with the plants of the active products, at the concentrations necessary for the fight against plant diseases, allows a treatment of the aerial parts of the plants, as well as a treatment of seedlings and seeds and of the soil.

In this case, the active compounds according to the invention can be used with success especially good, for the control of cereal diseases, such as, for example against Erysiphe types, or against diseases of grape, fruit and vegetable plantations, such as, for example, against types of Plasmopara or of Venturia, or of rice diseases, such as, for example, against types of Pyricularia. Other plant diseases, such as, for example, Septoria, Cochi lobolus, Pyrenophora and Pseudocercoosporella types, can be combined with the active compounds according to the invention, with Drechslera teres especially mentioned.

The active compounds according to the invention are also suitable for increasing harvesting. They are also of low toxicity and have a good compatibility with the plant.

The active products, employable according to the invention, are suitable, with a good compatibility with plants and a suitable toxicity for warm blood animals, for the fight against pests animals, preferably against insects, arachnids and nematodes, which occur in agriculture, in forestry, for the protection of stored products and materials as well as in the hygiene sector or the veterinary medicine sector. The products are active against normally sensitive and resistant types as well as against all or some of the stages of development. The aforementioned pests include: From the order of the isopods for example, Onicus asellus Armadillidium vulgare, Porcellio scaber.

From the order of the diplópodos, for example Blaniulus guttulatus.

From the order of the chilopoda, for example, Geophilus capophagus, Scutigera spec ..

From the order of the sinfilos, for example, Scutigerella immaculata.

From the order of the tisane, for example, Lepisma saccharina.

From the order of springtails, for example, Onychiurus armatus.

From the order of the orthopterans, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Germanic Blattella, Acheta domesticus, Gryllotalpa spp., Locusta micrato migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of dermápteros, for example, Formatic auricularia From the order of the Isoptera, for example, Reticult iermes spp.

From the order of the aphroids, for example, Pediculus humanus coporis, Haematopinus spp., Linognathus spp.

From the order of the malophagus, for example, Trichodectes spp., Damalinea spp.

From the order of the isanoptera, for example, Hercino thr ips femoralis, Thrips tabaci.

From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex spp., Rhodnius spp., Triatoma spp.

From the order of Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cruptomyzus ribis, Apphis fabae, Aphis pomi, Eriosoma lanigerum, Hylopterus arundinis, Phylloxera vastratrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalos iphum padi, Empoasca spp., Eucelis bilobatus, Nephotettix cicticeps, Lecannium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvate lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Li t hocollet is blancardel la, Hyponomeuta padella, Plutella macul ipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiel la, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trochoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophi pseudospretella, Cacoecia podana Capua retícula, Choris t oneura fumiferana, Clysia ambiguella, Homona magnanimous, Tortrix viridana.

From the order of Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chys ocepha la, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis , Anthonomus spp., Sitophilus spp., Ot iorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hyperas postica, Dermestes spp., Trogoderma spp., Antherenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon isis tialis, Costelytra zealandica.

From the order of Hymenoptera, for example, Diprion spp., Hoploacampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chysomia spp., Cuterebra spp., Gastrophilus spp. , Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Typula paludosa.

From the order of the syphonopsis, for example, Xenopsylla cheopis, Cerat ophy1 lus spp.

From the order of the arachnids, for example Scorpio maurus, Lactrodectus mactans.

From the order of mites, for example Acarus siró, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriphyes ribis, Phyllocopt oleivora route, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Pnanonychus spp. ., Tetranychus spp.

Plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsace, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp. The products according to the invention can be used with particular good success for the control of plant-damaging mites, such as against spider mites of green beans (Tetranychus urticae), or for the control of insects harmful to plants, such as caterpillars of the cockroach cabbage (Plutella macul ipennis), the larvae of the green leaf beetle of the horseradish (Phaedon cochleariae), as well as against the green rice cicada (Nephotetix cinticeps).

The products according to the invention also have herbicidal activity.

Depending on their respective physical and / or chemical properties, the active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, microencapsulated in polymer materials and coating compositions. for seeds, as well as formulations of cold fogging and hot ULV ".

These formulations are prepared in a known manner, for example by mixing the active agents with spreading agents, ie liquid solvents, liquefied gases, which are under pressure and / or solid support materials, optionally with the use of surfactants. , ie, emulsifies and / or dispersants and / or foam generating agents. In the case of the use of water as an extender agent organic solvents can also be used as auxiliary solvents. Suitable liquid solvents are: Aromatic hydrocarbons, such as xylene, toluene, or inaftals, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons. Such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as ciciohexano or paraffins, for example fráTcciones oil, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, meth ilet ilcetona, ilcetona metilsobut or cyclohexanone strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide as well as water. By liquefied gaseous support materials or extender agents are meant those which are gaseous at normal temperature and under normal pressure. For example, propellant gases for aerosols, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Suitable solid support materials are, for example, natural mineral flours, such as kaolins, clays, talc chalk, quartz attapulgite, montmorillonite, or land of diatomaceous and synthetic mineral flours, such as highly dispersed silicic acid, aluminum oxide and silcates. As solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules from organic material such as sawdust, coconut shell husks, corn cobs and tobacco stems. As emulsifying and / or foam formers are: for example nonionic emulsifiers and anionic surfactants such as esters polioxiet fatty acids ilenados ethers pol ilenados ioxie fatty alcohols, for example alquilaripoliglicoléter, alkylsulphonates, alkyl, ari lsul sulphonates, as well as albumin hydrolysates. Suitable dispersants are, for example, sulfite lignin blends and methylcellulose.

They can be used in adhesive formulations such as carboxymethylcellulose, natural and synthetic polymers powdery, granular or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate as well as natural phospholipids, such as cephalin and lecithin and synthetic phospholipids. Other additives can be mineral and vegetable oils . colorants such as inorganic pigments can be used, for example iron oxide, titanium oxide, Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, zinc.

The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides. to expand, for example, the spectrum of activity or eliminate the development of resistance. In many cases synergistic effects are obtained in this way, that is to say that the activity of the mixture is greater than the activity of the individual components.

Suitable components of the mixture are, for example, the following compounds: Fungicides: Aldi orph, ampropylfos, Ampropy1 fos -potas io, andoprim, Anilazin, Azaconazole, Azoxys t robin, benalaxyl, Bonodanil, Benzamacril, Benzamacryl-isobutyl, bialaphos, binapacryl, Biphenyl, Bitertanol, Blas you cdi in-S, bromuconazole, Bupirimat, Buthiobat, Calcium Polysulfide, Capsimycin, Captafol, Captan, Carbendazin, Carboxin, Carvon, Chinole trhionat (Quinomethionat), Chlobenthiazon, Chlor phenazole, Chloroneb, Chloropicrin, Chlorothalonil, Chlozolinat, Clozycalon, Cufraneb, Cymoxanil, Cyproconazole, Cyprodinil, Cyprofuram, Debacarb, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazole, Dimethirimol, Dimethomorph, Diniconazole, Dinicona zol -M, Dinocap, Diphenylamine, Dipyri thione, Ditalimphos, Dithianon, Dodemorph, Dodine, Drazoxolon, Ediphenphos, Epoxiconazole, Etaconazole, Ethyrimol, Etriadiazole, Famoxadon, Feenapanil, Fenarimol, Fenbucone zol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fent inacetat, Fent ihidroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluorconazole, Fluquinconazole, Flurprimidol, Flusilazol, Flusalfamid, Flutolanil, Flutriafol , Folpet, Foset yl-Aluminum, Fosetyl-sodium, Ftalid, Fuberidazole, Furalaxyl, Fumamerpyr, Furcarbonil, Furconazole, Furcona zo-1cis, Fumercyclos, Guza t in, Hexachlorobenzene, Hexaconazole, Hymexazole, Imazalil, Imibenconazole, Iminoctadin, Iminoctadinealbesilate, Iminocadinetriacetate, Iodocarb, Ipconazole, Iprobenfos (PPI), Iprodione, Irumamycin, I soprothiolan, I sovaledione, Kasugamycin, Kresoxim-methyl, cohre preparation. , such as: copper hydroxide, naphthenate of copper, copper oxychloride, copper sulfate, copper oxide, copper oxide and mixture of Boerdeaux, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanypyrim, Mepromil, Metalaxyl, Metconazole, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin , Myclobutanyl, Myclozolin, Dimethyl nickyl iocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadyl, Oxamacarb, Oxolilnicacid, Oxycaboxim, Oxyfenthiin, Paclobutrazol, Pefurazoat, Penconazole, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, Probenazole, Prochloraz , Procymidon, Propamocarb, Propane ine. sodium, - Propi cona zól, Propiconazol, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Pyroxyfur, Quinconazole, Quintozcen (PCNB), Sulfur and sulfur preparations, Tebuconazole, Tecloftalam, Tecnazen, Tercyclacis, Tet racona zol, Thiabendazole, Thicyofen, Thi fluzamide, T iphanate-met i lo, Thiram, Tioxymid, Tolclofos-methyl, Tolyfluanid, Tridmefon, Triadimenol, Triazbutanil, Triazoxid, Trichlamid, Tricyclazole, Tridemorph, Triflumizol, Triforin, Triticonazole, Uniconazole, Valdamycin A, Vinclozolin, Vinconazole, Zarilamide, Zineb, Ziram, as well as Dagger G, OK-8705, OK-8801, a- (1,1-dimethylethyl) -β- (2-phenoxyethyl) - lH-1, 2,4-triazole-1-ethanol, a- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2-triazole-1-ethanol, a- (2, 4-dichlorophenyl) -β-methoxy-α-methyl-1H-1, 2,4-triazol-1-ethanol, a- (5-methyl-1,3-dioxa-5-yl) -β- [ [4- (trifluoromethyl) 1-phenyl] -methyl] -1H-1, 2,4-triazole-1-ethanol, (5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl -5- (lH-1, 2,4-tri-azol-l-yl) -3-octanone, (E) -a- (methoxyimino) -N-methyl-1-2-phenoxy-phenylacetamide,. { 2-methyl-l [[[1- (4-methylphenyl) -ethyl] -amino] -carboni 1] -propyl} -carbaminate of 1-isopropyl, 1- (2,4-dichlorophenyl) -2- (lH-1, 2,4-triazol-1-yl) -ethanon-O- (phenylmethyl) -oxime, 1- (2- methyl-1-naphthalene) -lH-pyrrole-2, 5-dione, 1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, 1- [(diiodomethyl) -sulfonyl] -4-methyl-benzene, 1 - [[2- (2,4 -dichlorophenyl) -l, 3-dioxolan-2-yl] -met-il] -lH-imidazole, 1 [[2- (4-chlorophenyl) -3-phenyloxyranyl] -methyl] -1H-1,2,4-triazole , 1- [1- [2- [(2,4-dichlorophenyl) -methoxy] -phenyl] -ethenyl] -lH-imidazole, l-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6' -dibromo-2-methyl-4 '-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide, 2,2-dichloro-N- [1- (4-chlorophenyl) - ethyl] -l-ethyl-3-methyl-cyclopropanecarboxamide, 2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate, 2,6-di-chloro-N- (4-trifluoromethylbenzyl) -benzamide, 2 , 6-dichloro-N- [[4- (t ri f1-uormet-1) -phenyl] -methyl] -benzamide, 2- (2,3-, 3-triiodo-2-propenyl) -2H-tetrazole, 2- [(1-Methylethyl) -sulfonyl] -5- (trichloromethyl) -1,3-thiadiazole, 2- [[6-deoxy-4-0- (4-0-methyl-β-D-glycopyranosyl) -a] -glucopyranosyl] -amino] -4-methoxy-1H-pyrrolo [2, 3] pyrimidine-5-carbonitrile, 2-am inobutane, 2-bromo-2- (bromomethyl) -pent anodinitrile, 2-chloro-N- (2,3-dihydro-l, l, 3-t rimet il-lH-iden-4-yl) -3-pyridinecarboxamide, 2 -chloro-N- (2, 6-dimet i lphenyl) -N- (i soriocianatomet i 1) -acetamide, 2-phenylphenol (OPP), 3, -dichloro.1- [4- (difluoromethoxy) -phenyl] - lH-pyrrole-2, 5-dione, 3,5-dichloro-N- [cyano (1-methyl-2-propynyl) -oxy] -methyl] -benzamide, 3- (1, 1-dimethylpropyl-1- oxo-lH-inden-2-carbonitrile, 3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] -pyridine, 4-chloro-2-cyano-N, N-dimethyl-5- (4 -methyl phenyl) - 1H-imidazole-1-sulphonamide, 4-methyl-tetrazole [1,5-a] quinazolin-5 (4H) -one, 8- (1,1-dimethyl-ethyl) -N-ethyl -N-propyl-1,4-dioxaspiro [4.5] decan-2-methanolamine, 8-hydroxyquinoliphatic acid, 2- [(phenylamino) -carbonyl] -hyzarazide of 9H-xant-9-carboxylic acid. (1-methylethyl) -3-methyl-4- [(3-methylbenzoyl) -oxy] 2,5-thiophenedicarboxylate, cis-1- (4-chlorophenyl) -2- (lH-1, 2,4-triazol-1-yl) -. cycloheptanol, cis .4 - [3 - [- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimet-1-morpholine, ethyl- [(4-chlorophenyl) -azo] -cyanoacetate hydrochloride. , potassium bicarbonate, sodium salt of methane-rutiol, methyl-1- (2, 3-dihydro-2, 2-dimethyl-lH-iden-1-yl) -1H-imide zol-5-carboxylate, methyl-N- ( 2,6-dimethylphenyl) .N. (5-isoxazoli Icarbonil) -DL-alaninate, methyl-N- (chloroacetyl) -N- (2,6-dimethyl phenyl) -DL-alaninate, N- (2,3-dichloro- -hydroxy phenyl) -1- metho-cyclohexane oxamide, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) -acetamide, N- (2,6-dimethyl phenyl) -2- methoxy-N- (tetrahydro-2-oxo-3-thieni 1) -acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -1 , 4,5,6-tetrahydro-2-pyrimidinamine, N- (4-hexylphenyl) -1,5,5,6-tetrahydro-2-pyrimidinamine, N- (5-Chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide, N- (6-methoxy) -3-pyridinyl) -cyclopropanecarboxamide, N- [2, 2, 2-trichloro-l- [(chloroacetyl) -amino] -ethyl] -benzamide, N- [3-chloro-4,5-bis- (2-proponyloxy) -phenyl] N '- methoxymethanomidoamide, Sodium salt of N-formi 1-N-hydroxy-DL-alanine, 0,0-diethyl- [2- (dipropylamino) -2-oxoethyl] -ethyl-phosphoramidothioate, O-methyl-S-phenyl-phenylpropylphosphoramidothioate, S-methyl- 1, 2, 3-benzenethiadiazole-7-carbothioate, spiro [2 H] -l-benzopyran-2, 1 '(3' H) -isobenzofuran] 3'-one.

Bactericides Bronopol, Dichlorophen, Nitrapyrin, nickel dimethyldicarboxylate, Kasugamycin, Ochilinon, furancarboxylic acid, Oxytet racyclin, Probenazol, Steptomycin, Tecloftalam, copper sulfate and other copper preparations.

Insecticides / Aquariums / Nematocides: Abamectin, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadiracht in, Azinphos A, Azinphos M, Azocyclotin, Bacillus t rhuringiensis, 4-bromo-2- (4-chlorophenyl) -1- ( ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacylut rhin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpi ridaben, Cadusfos, Crbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyf os, Chlorfenvinphos, Chl r flu zuron, Chlormephos, N - [(6-chloro-3-pyrimidyl) -methyl] -N'-cyano-N-methyl-et nimidoamide, Chlorpyri fos , Chlorpyri fos, M, Cis-Resmethrin in, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos , Diclipos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dymethy1 vinphos, Dioxathi oin, Disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiophencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos, Fenamiphos, Fenazaquin, Fenbut at inoxid, Feni t rothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipromil, Fluazinam, Fluazuron, Flucycloxuron, f lucyt rhinat, Flufenoxuron, Flupeprox, Fluvalinate, Fonophos, Formathion, Posthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaf lumuron, Hexythiazox, Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalo t rhin, Lufenuron, Malatrhion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methida thion, Methiocarb, Methomyl, Metocarb, Milbemectin, Monocrot ophos, Moxidectin, Naled, NC 184, Nitenpyram, Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Permethrin, Phenthoat, Phoat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profernophos, Promecarb, Propaphos, Propoxur, Prothiophos, prothoat, Pymetrozin, Pyrach lophos, Pyradaphent hion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyproxifen, Quinalphos.

Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Teburfenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbara, T-erbufos, Tet rachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlofon, Triflumuron, Trimetchacarb, Vamidothion, XNC, Xylylcarb, Zetamethrin.

A mixture with other known active ingredients, such as herbicides or even compost and growth regulators is also possible.

The active compounds can be used as such in the form of their formulations or the forms of application prepared from the above, such as ready-to-use solutions, suspensions, injectable powders, pastes, powders, solvents, dusts and granules. The use is carried out in a conventional manner, for example by watering, spraying, sprinkling, spreading, dusting, foaming, brush application, etc. If applicable, the active products also according to the ultra low volume process or the preparation of active product or the active product itself will be injected into the soil. The seeds of the plants can also be treated.

When the active compounds according to the invention are used for the control of microorganisms, the application amounts can vary within wide limits depending on the type of application. When parts of the plants are treated, the active product application amounts are generally between 0.1 and 10,000 h / ha, preferably between 10 and 1.00 g / ha. When the seeds are treated, the amounts of application of active compound are, in general, between 0.001 and 50 g per kilogram of seeds, preferably between 0.01 and 10 g per kilogram of seed. In the case of soil treatment, the application amounts are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

Also when used against animal pests the products according to the invention can present in customary formulations in the trade as well as in the forms of application prepared from these formulations in mixtures with synergists. The synergists are compounds by which the effect of the active products is increased, without the added synergist having to be active by itself.

The active ingredient content of the application forms prepared from the commercially available formulations can vary within wide limits, the concentration of active product of the application forms can be from 0.0000001 to 95% by weight of product active, preferably between 0.0001 and 1% by weight.

The application is carried out in a form adapted to the forms of application.

The preparation and use of the active compounds according to the invention is apparent from the following examples: Examples of obtaining Example 1 They are added dropwise in a mixture consisting of 20.8 g (0.1725 mole) of 2-cyano-aniline and 250 ml of pyridine, at 5 to 10 ° C, with stirring 38.1 g (0.15 mole). ) of 3,4-di-chloro-isothiazolyl-5-carbonyl chloride over 10 minutes. After the addition was complete, the reaction mixture was combined with 70 ml of absolute tetrahydrofuran and 30 ml of pyridine, allowed to warm to room temperature and then stirred for 75 minutes. At room temperature. The reaction mixture is then evaporated under reduced pressure. The remaining residue is stirred with 800 ml of water and 800 ml of ethyl acetate. The precipitate formed in the basic mixture is Separate by filtration, wash with ethyl acetate and dry. In this way, 31.7 g of a crystalline product with a melting point of 191 to 193 ° C are obtained.

The aqueous phase is separated from the biphasic filtrate and extracted twice with 150 ml of ethyl acetate each time. The combined organic phases are dried over sodium sulphate and concentrated by evaporation under reduced pressure. The remaining residue is stirred and stirred with 100 ml of petroleum ether and 25 ml of ethyl acetate. The solid product formed is separated by suction filtration, washed further with ethyl acetate and dried.

In this way, a total of 40 g (89% of the theory) of the 2'-cyano-3,4-dichloro-isothiazol-5-carboxani 1-ida is obtained in the form of a solid substance with a melting point. from 191 to 193 ° C.

Obtaining the starting product 8.92 g (0.045 mole) of 3,4-dichloro-isothiazol-5-carboxylic acid are added dropwise at room temperature over a period of 5 minutes, with stirring, 146 g (1.23 moles). ) of thionyl chloride. Then 4 drops of dimethyl formamide are added and the reaction mixture is heated at reflux for 1 hour. The reaction mixture is then cooled to room temperature and concentrated by evaporation under reduced pressure. In this manner, 12.19 g of 3,4-dichloro-isothiazole-5-carbonyl chloride are obtained in the form of an orange-colored oil.

Example 2 They are added to a mixture consisting of 32.3 g (0.164 moles) of 3,4-dichloroisothiazole-5-carboxyamide and 245 ml of glacial acetic acid, under stirring, at room temperature, 15 g (0.164 moles) of N-formi 1-N-hydroxymethylmethylamine. Subsequently, 37 g (0.362 mol) of concentrated sulfuric acid are added dropwise with stirring at room temperature and the reaction mixture is cooled with ice.

The reaction mixture is then stirred for 29 hours at room temperature and then combined with 400 ml of water under ice-cooling. The formed mixture is extracted four times with 200 ml of methylene chloride each time, the combined organic phases are dried over sodium sulphate and then concentrated by evaporation under pressure. reduced. The remaining oleaginous residue is chromatographed with ethyl acetate on silica gel. After concentration by evaporation of the eluate, 20.7 g (42.6% of theory) of N- (N-formyl-N-methyl-aminomethyl) -3,4-dichloro-isothiazole-5-carboxamide are obtained in the form of a crystalline solid substance with a melting point of 87 up to 88 ° C Obtaining the starting substance: Add to dropwise 82 g (1.2 mol) of concentrated ammonia at 0 to 10 ° C in the course of 30 minutes, with stirring, 50.1 g (0.2 mol) of sodium chloride. 3,4-di-cl-isothiazole-5-carbonyl. After the addition is complete, 41 g (0.6 mol) of concentrated ammonia are again added and diluted with 70 ml of water. Allow to warm to room temperature and stir for 45 minutes at this temperature. The precipitate formed is separated by suction filtration, washed successively with water and with petroleum ether and dried. In this way, 32.3 g (81.8% of theory) of 3,4-dichloro-isothiazole-5-carboxyamide are obtained in the form of a solid substance with a melting point of 156 to 158 ° C.

According to the methods indicated above, the products of the formula (I) indicated in the following table are also prepared.

Table 1.

Table 1 (Continuation).

Table 1 (Continued) Table X (Continued).

*) The determination of the log P value was carried out according to EEC Directive 79/831, Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid). **) The values ? designate maximums in the UV spectrum.

Examples of Use Amplo A Test with Pyticularia (rice) / induction of resistance.

Solvent: 2.5 parts by weight of acetone. Emulsifier: 0.06 parts by weight of alkylaryl polyglycol ether.

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and the concentrate is diluted with water and with the indicated amount of emulsifier to the desired concentration.

To verify the resistance inducing activity, young rice plants are sprayed with the preparation of the active product in the indicated application amount. After 5 days from the treatment, the plants are inoculated with an aqueous suspension of spores of Pyricularia oryzae. Then they are arranged in the plants in a greenhouse with a relative humidity of 100% and a temperature of 25 ° C.

After 4 days, from the inoculation, the evaluation is carried out. In this case 0% means a degree of activity that corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed.

The active products, the application quantities and the test results can be seen in the following table.

Table A Test with Pyricularia (rice) / resistance induction.

Table A (Continued) Test with Pyricularia (a? Toz) / induction of resistance.

Example B Trial with Phaedon larvae Solvent: 7 parts by weight of dimethyl formamide. Emulsifier 1 Part by weight of alkylaryl polyglycol ether.

To obtain a suitable composition of the active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica olerácea) are treated by being dipped into the preparation of the active compound at the desired concentration and covered with larvae of the horseradish beetle (Phaedon cochlearie), while the leaves are still moist.

The degree of destruction is determined after 7 days and expressed as a percentage. In this case, an activity level of 100% means that they destroyed all larvae of the beetles, while a degree of activity of 0% means that no larvae of the beetles were destroyed.

The active products, the concentrations of the active products and the test results can be seen in the following table.

Table B Test with Phaedon larvae / insects harmful to plants.

Active product ConcentraDegree of prodestruction active ducto in% to corporal in% in weight of 7 days 0.1 100 (3) Example C Test with plutella Solvent 7 parts by weight of dimethyl 1 formamide. Emul s ionant and 1 part by weight of alkylaryl polyglycol ether.

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

Cabbage leaves (Brassica olerácea) are treated by being dipped into the preparation of the active compound of the desired concentration and covered with caterpillars of the cabbage moth (Plutella xylostella), while the leaves are still moist.

After 7 days, the degree of destruction is determined. In this case, an activity level of 100% means that all the caterpillars, while an activity level of .0! means that no caterpillar was destroyed.

The active products, the concentrations of the active products and the test results can be seen in the following table. Table C Test with PluteHa / Insects harmful to plants.

Example D Test with Venturia (apple tree) / protector Solvent 4 1 Parts by weight of acetone. Emulsifying 3 parts by weight of alkylaryl polyglycol ether.

To obtain a convenient preparation of the active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvents and emulsifier and the concentrate is diluted with water to the desired concentration.

To test the protective activity, young plants are sprayed with the preparation of the active compound with the indicated application amount. After drying of the spray-applied coating, the plants are inoculated with an aqueous suspension of conidia of the anthracnose pathogen of the Venturia inaequalis apple tree and then remain for approximately 1 day at 20 ° C and with a relative humidity of 100% in a booth. incubation.

The plants are then placed in the greenhouse at a temperature of about 21 ° C and a relative humidity of about 90%.

The evaluation occurs 12 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the controls, while a degree of activity of 100% means that no type of attack is observed.

The active products, the concentrations of the active products and the test results can be seen in the following table.

Table D Venturia test (apple tree) / protector Active product Quantity Applied degree of product activity in% active in g / ha According to the invention 100 96 (fi) Example E Test with Leptosphaeria nodorum (wheat) / protector Solvent: 10 Pairs by weight of N-methyl-pi rrol idona. Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether.

To obtain a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test the protective activity, young plants are sprayed with the preparation of the active compound with the indicated application amount. After drying the spray applied coating, the plants are sprinkled with a suspension of Leptosphaeria nodorum spores. The plants remain 48 hours at 20 ° C and 100% relative humidity in an incubator.

The plants are placed in a greenhouse at a temperature of approximately 15 ° C and with a relative humidity of 80%.

The evaluation is carried out 10 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed.

The active products, the application quantities and the test results can be seen in the following table. Table E Test with Leptosphaeria nodorum (Wheat) / protector 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.

Having described the invention as above, the content of the following is claimed as property.

Claims (10)

Claims

1. Isot iazolcarboxamides of the formula characterized because R means a radical of the formula where R1 means cyano, phenyl or cycloalkyl with 3 to 7 carbon atoms, R means a radical of the formula where R 'means -C (CH3) 3, -CH-C2H5, -CH-C2H5, C2 2H "5CH- cycloalkyl with 3 to 7 carbon atoms means - CH2-S-R" where R means C 1 -C 6 -alkyl, or means halogen and / or C 1 -C 6 -alkyl optionally substituted by phenyl, R means a radical of the formula where R 'means hydrogen or N, N-dialkylamino with 1 to 4 carbon atoms means a radical of the formula where R- means hydrogen or alkoxy with 1 carbon atoms and R means alkoxy having 1 to 4 carbon atoms, alkyl having 1 to 6 carbon atoms, phenyl optionally substituted by halogen or phenoxy means optionally substituted by halogen, or R5 means phenoxy substituted, if appropriate, by halogen and R 'means hydrogen, or R means a radical of the formula -CH2 - CH2-0 - R, where R means alkyl with 1 to 4 carbon atoms, R means alkyl with 1 to 4 carbon atoms and R means hydrogen or a radical of the formula R means a radical of the formula where R10 means -halogen, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms and n means integers of 0

2. A process for the preparation of isothiazolecarboxyamides of the formula (I) according to claim 1, characterized in that a) 3,4-dichloroisothiazol-5-carbonyl chloride of the formula is reacted it is reacted with amines of the formula H2N-R (III) in which R has the meanings indicated above, if appropriate in the presence of an acid-binding agent and, if appropriate, in the presence of a diluent, or 3, 4-Dichloro-isothiazole-5'-carboxyamide of the formula is reacted it is reacted with hydroxy compounds of the formula HO-CH2-X (V) in which X means a radical of the formula where R4, R5 R6 and R8 have the meanings indicated above, the presence of a diluent and in the presence of a water-dissociating agent.

3. Agents for the protection of plants against attack due to undesirable microorganisms and against animal pests, characterized in that they have a content in at least one isothiazolecarboxyamide of the formula (I) according to claim 1, in addition to extenders and / or surfactant products.

4. The use of the isothiazolecarboxyamides of the formula (I) according to claim 1, for the protection of plants against attack due to undesirable microorganisms and animal pests.

5. A procedure for the protection of plants against attack due to undesirable microorganisms and animal pests, characterized in that the isothiazolecarboxyamides of the formula (I) according to claim 1, on the plants and / or on their environment.

6. The process for obtaining agents for the protection of plants against attack due to undesirable microorganisms and animal pests, characterized in that the isothiazolecarboxyamides of the formula (I) according to claim 1 are mixed with excipients and / or with surfactant products.

7. The isothiazolecarboxyamide according to claim 1, characterized by the formula

8. The isothiazolecarboximide according to claim 1, characterized by the formula

9. The carboxyl amide solution according to claim 1, characterized by the formula

10. The isotia zolcarboxyamide according to claim 1, characterized by the formula