MXPA06005775A - N-arylhydrazine derivatives for seed treatment - Google Patents

Abstract

Method for the protection of seeds from soil pests comprising contacting the seeds before sowing and/ or after pregermination with a compound of formula (I):wherein W is chlorine or trifluoromethyl;X and Y are each independently chlorine or bromine;R1 is alkyl, alkenyl, alkynyl, or cycloalkyl which may be substituted with 1 to 3 halo -gen atoms, or alkyl which is substituted by alkoxy;R2 and R3 are alkyl or may be taken together to form cycloalkyl which may be unsubsti -tuted or substituted by 1 to 3 halogen atoms;R4 is hydrogen or alkyl, or the enantiomers or salts thereof, in pesticidally effective amounts. Seed, comprising compounds of formula (I).

Description

N-arylhydrazine derivatives useful as the seed treater before sowing and / or after pregermination. DESCRIPTIVE MEMORY The present invention provides a method for the protection of seeds which comprises contacting the seeds before sowing and / or after pre-germination with a compound of the formula I. wherein W is chloro or trifluoromethyl; X and Y are each, independently of each other, chlorine or bromine, Rx is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, or C 3 -C 3 cycloalkyl, which may be substituted with 1 to 3 halogen atoms, or C 2 -C 4 alkyl which may be substituted by C 1 -C 4 alkoxy; R2 and R3 are -Ci-Cg alkyl or they may be taken together to form a C3-C6 cycloalkyl, which may be unsubstituted or substituted with 1 to 3 halogen atoms; R 4 is hydrogen or C 1 -C 6 alkyl, or the enantiomers or salts thereof, in amounts that are effective as pesticides. The invention also relates to seeds containing the compounds of the formula I. The invention also relates to the use of the compounds of formula I for the protection of seeds against pests at ground level. A typical problem that occurs in the area of seed protection is the need to reduce the dose of the active ingredient in order to reduce or avoid unfavorable environmental or toxicological effects while still allowing effective control of the pest. ground level or terrain. Another problem faced concerns the need to have seed protection agents that are effective against a broad spectrum of pests at the soil or soil level. There is also a need for seed protective agents which combine the immediately known activity with a prolonged control, that is, a rapid effect with a lasting effect or action. Another difficulty in relation to the use of seed protection pesticides is that the repeated and exclusive application of a single pesticide compound produces in many cases a rapid selection of soil pests, which have developed a natural resistance or adopted against of the active compound in question. Therefore, there is a need to be able to have seed protection agents which help to prevent or overcome the resistance. Therefore, the present invention was aimed at providing compounds that solve the problems of reducing the dosage rate and / or improving the immediate effect with prolonged control and / or resistance management. The authors of the present invention have found that these objectives can be achieved partially or totally by the compounds of the formula I and the compositions containing them.

BACKGROUND OF THE INVENTION Insecticidal and acaricidal activity in the protection of plants in the agricultural area of some of the compounds of formula I has been described in EP-A 604 798 and also in the publication of J.A. Furch et al, "Amidrazones: A Novel Class of Insect Control Agents," ACS Sym-posium Series 686, Am. Chem. Soc. , 1998, Chapter 18, p. 178 ff and also in D.G. Jun et al., "Cycloalkyl-substituted Amidrazo-nes: A Novel Class of Insect Control Agents," ACS Symposium Series 686, Am. Chem. Soc. , 1998, Chapter 19, p. 185 ff. The activity of the compounds in the protection of plants against agricultural pests does not suggest their usefulness in the protection of seeds, which requires, for example, activity against pests at ground level, compatibility with the conditions soil, for example, concerning the fixation of the compound with the soil), a negligible toxicity when applied to the seed, and an adequate movement to achieve the necessary bioavailability (in the soil or plant). In a surprising way it has now been discovered that the compounds of the formula I are suitable for protecting the seeds. The compounds of formula I can be prepared according to the preparation methods described in the aforementioned patent EP-A-604 798 or the modifications thereof. In the definition of formula I shown above, the substituents have the following meanings: "Halogen" will be taken to mean fluoro, chloro, bromo and iodo. The term "alkyl", as used herein, refers to a branched or straight or unbranched saturated hydrocarbon group with 1 to 4 or 6 carbon atoms, especially C 1 -C 3 alkyl, such as methyl, ethyl, propyl , 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1 , 1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl , 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2 -methylpropyl. "Alkoxy" refers to a straight or branched chain alkyl group with 1 to 4 carbon atoms (methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl) attached to through an oxygen bond, at any bond in the alkyl group. Examples include methoxy, ethoxy, propoxy and isopropoxy. "Cycloalkyl" refers to a ring of carbon atoms saturated with 3 to 6 members, ie cyclopropyl, cyclobuyl, cyclopentyl or cyclohexyl. As regards the intended use of the compounds of the formula I, particular preference is given to the following meanings of the substituents, in each case by themselves or in combination: The compounds of the formula I are preferred in the which W is trifluoromethyl. In addition, the compounds of the formula I in which X and Y are both chlorine are preferred. In addition, the compounds of the formula I in which R 1 is C 1 -C 3 alkyl, especially ethyl, are preferred. In addition, the compounds of the formula I in which R2 and R are both methyl are preferred.

On the other hand, the compounds of the formula I are preferred in which R2 and R3 form a cyclopropyl ring unsubstituted or substituted by 1 to 3 halogen atoms, especially chlorine or bromine. Furthermore, particularly preferred are the compounds of the formula I wherein R2 and R3 form a cyclopropyl ring which is substituted by 2 halogen atoms. Furthermore, particularly preferred are the compounds of formula I, wherein R 2 and R 3 form cyclopropyl ring, which is substituted by 2 chlorine atoms. Particularly preferred are the compounds of the formula I wherein R2 and R3 form a 2,2-dibromocyclopropyl ring. Preferred are also the compounds of formula I wherein R 4 is C 1 -C 3 alkyl, especially methyl. Particularly preferred are the compounds of the formula I, wherein R2, R3 and R4 are all methyl. Furthermore, particularly preferred are the compounds of the formula I, wherein R2, R and R4 form a 1-methyl-2,2-dibromocyclopropyl moiety or group. In addition, the compounds of the formula I in which W is trifluoromethyl are preferred; X and Y are each independently chlorine or bromine; R 1 is C 1 -C 6 alkyl, R 2 and R 3 are C 1 -C 6 alkyl or they can be taken together to form a C 3 -C 6 cycloalkyl, which is substituted by 1 or 2 halogen atoms; R 4 is C 1 -C 6 -alkyl, or the enantiomers or salts thereof. Of particular preference are the compounds N-ethyl-2,2-dimethylpropionamide-2- (2,6-dichloro-alpha, alpha, alpha-trifluoro-p-totyl) hydrazone and N-ethyl-2,2-dichloro-l - methylcyclopropane carboxamide, 2- (2,6-dichloro-alpha, alpha, alpha-trifluoro-p-tolyl) hydrazone. In addition, particularly preferred with respect to the use in the present invention is the compound of the formula (I-1) (N-ethyl-2,2-dimethylpropionamide-2- (2,6-dichloro-alpha, alpha, alpha-trifluoro -p-tolyl) -hydrazone): Furthermore, particularly preferred in relation to the use in the present invention is the compound of the formula (1-2) (N-ethyl-2,2-dichloro-l-methylcyclopropanecarboxamide-2- (2,6-dichloro-alpha) , alpha, alpha-trifluoro-p-tolyl) hydrazone): With respect to their use, particularly preferred are the I-A compounds compiled in the following tables. In addition, the groups mentioned as substituents in the tables in themselves, independently or in combination with those mentioned, represent the preferred embodiment of the substituent in question: As regards its use, particularly preferred are the adducts with hydrochloric acid, acid maleic, dimaleic acid, fumaric acid ,. Dumouaric acid, methanesulphonic acid, methane sulfenic acid, and succinic acid of the compounds of the following tables: (I-A) Table A The compounds of the formula I are suitable for the protection of the seeds against soil pests, especially against those selected from the following list: Millipedes (Diplopoda), hemiptera (homoptera and heteroptera), Orthoptera, Lepidoptera (Lepidoptera), for example , Agrotis Ípsilon, Agrotis segetum, Chilo ssp, Euxoa ssp. , Momphidae, Ostrinia numbilalis, and Phthorimaea operculella, Beetles (Coleoptera), for example, Agriotes lineatus, Agriotes obscurus, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Ctenicera ssp. , Di abro tica longicomis, Diabrotica speciosa, Diabrotica semi - punctata, Diabrotica virgifera, Limonius californicus, Melano - tus communis, Otiorrhynchus ovatus, Phyllobius Pyri, Phyllophoe sp. , Phyllophaga custard, Phyllophaga triticophaga, Phylopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Si tona lineatus and Sitophilus granaria, Flies (Diptera), for example, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cor-dylibia anthropophaga, Dacus cucurbi tae, Dacus oleae, Dasineura brassicae, Delia antigue, Delia coarctata, Delia platura, Delia radicum, Famia canicularis, Gasterophilus intestinalis, Geomyza tripunctata, Glossina morsi tans, Haematobia irri tans, H plodi -plosis equestris, Hypoderma lineata, Liculia caprina, Lucilia cuprina, Lucilia sericate, Lycoria pectoralis, Mayetiola destructor, Muscina stabulans , Oestrus ovis, Opomyza florum, Osci - nella fri t, Pegomya hysocyami, Phorbia antigua, Phorbia brassi cae, Phorbia coarctata, Psila rosae, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Typula olerácea and Typula paludosa, Thrips (thysanoptera), e. g. Simple Thrips, Ants (Hymenoptera), for example, Atta capiguara, Atta cep halotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Monomorium pharaonis, Solenopsis germínata and Solenopsis invicta, Pogonomyrmex ssp. And Pheidole megacephala, termites (Isoptera), for example, Coptotermes ssp. , springtails (Collembola), for example Onychiurus ssp.

In particular, the mixtures of the invention are suitable for combating pests belonging to the orders dipte-ros, coleoptera, lepidoptera and isoptera. In addition, the use of the compounds of the formula I and compositions containing them to combat pests belonging to the order diptera, especially the Delia species, is particularly preferred. Furthermore, the embodiment of the present invention consisting of the use of the compounds of the formula I and the compositions containing them for combating pests belonging to the order of the coleoptera, especially the species Diabrotica and Elateridae (filamentous worms), is preferred. Furthermore, the use of the compounds of the formula I and the compositions containing them are preferred for combating pests belonging to the order of the isoptera. The compounds of the formula I can be used in the protection at ground level. The protection of the seed is preferred. Especially preferred is the protection of the seeds belonging to the group of cereals (for example, wheat, barley, rye), sugarcane, sugar beet, corn, sorghum, girazol, cotton, rice, peas, rapeseed, potato and crops marketed from the garden, such as rice, wheat, barley or rye. The compounds of formula 1 are effective through direct and indirect contact and ingestion and also through trofalaxis and transfer. Formulations for the treatment of conventional seeds include, for example, the fluid concentrations FS, the LS solutions, the powders for the dry treatment DS, the powders available in the WS water or the granules for the treatment of pulp, the soluble powders in water SS and emulsions ES. The application to the seeds is done before sowing either directly on the seeds or after the pregermination thereof.

For use according to the present invention, the compounds I can be converted into the customary formulations, for example, solutions, emulsions, suspensions, fine powders, powders, pastures and granules. The use depends on the particular objective and it is intended to ensure in each case a cold and uniform distribution of the compound on the seed, according to the invention. The formulations were prepared in the known manner, for example, by spreading the active ingredient with the aid of solvents and / or vehicles, if desired using emulsifiers and dispersants. Suitable solvents / auxiliary agents are essentially the following: water, aromatic solvents (for example, solvesse, xylene products), paraffins (for example, mineral or petroleum fractions), alcohols (for example, methanol, butane, pentanol, benzyl alcohol), ketones (eg, cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycolic diacetate), glycols, fatty acid dimethylamide, fatty acids and fatty acid esters. In principle, you can also use mixtures of solvents; - vehicles, such as ground natural minerals (eg, kaolins, clays, talc, chalk) and ground synthetic minerals (eg, highly dispersed silica, silicates), emulsifiers, such as emulsifiers or emulsifiers nonionics and anions (eg, polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulphonates) and dispersants, such as liquor sulfite and methylcellulose waste liquors. Suitable surfactants are the alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalene sulphonic acid, phenolsulfonic acid, dibutylnaphthalene sulfonic acid, alkylarylsulfonates, alkyl sulphates, alkylsulfonates, fatty alcohol sulfate, fatty alcohol glycol ethers of sulfated fatty acids, other condensations of the naphthalene and sulfonated naphthalene derivatives formaldehyde, the naphthalene condensates of naphthalene sulfonic acid with phenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol / ethylene oxide condensations, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropyl, acetyl ether polyglycol lauryl alcohol, sorbitol esters, lignin sulphite bleach liquors and block copolymers of methylcellulose and ethylene oxide / propylene oxide. Substances that are suitable for the preparation of direct spray solutions, emulsions, pastes or oil dispersions are fractions of mineral or petroleum oil with a medium to high boiling point, such as kerosene or diesel oil, as well as tar oils. coal and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone , isophorone, strongly polar solvents, for example dimethyl, sulfoxide, N-methylpyrrolidone and water. Powders, spreading materials and fine or flying powders can be prepared by mixing concomitantly active substances and their solid vehicles. The granules, for example the coated granules, the impregnated granules and the homogeneous granules, can be proposed by agglomerating the active ingredients with solid carriers or carriers. Examples of solid carriers are mineral soils such as silicates, silicates, talc, kaolin, atta-clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate , magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urease and plant-derived products, such as cereal flour, sawdust, bark tree, wood sawdust and rice husk sawdust, powdered cellulose and other solid vehicles. The tackifiers can be incorporated to improve the adhesion of the active materials on the seeds after the treatment. The additional adhesives are the EO / PO surfactant copolymers, but also the polyvinyl alcohols, polyvinylpyrrolidones, poly-acrylates, polymethacrylates, polybutanes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol (MR), Polimin ( MR) polyesters, polyurethanes and copolymers derived from these polymers In general, the formulations comprise from 0.01 to 95%, by weight, preferably from 0.1 to 90%, by weight, of the active ingredient. they are used with a purity from 90% to 100%, preferably 95% up to 100% (according to the NMR thickness). Below are examples of the formulations: 1. Products for direct application or for application after the application. dilution with water A) Soluble Concentrates (LS) The solution 10 pests, by weight, of the active compounds in water or in a solvent soluble in water. As an alternative, wetting agents or other auxiliaries are incorporated. The active compound dissolves upon being diluted with water.

B) Dispersible Concentrates (DC) 20 pests, by weight, of the active compounds were dissolved in cyclohexanone with incorporation of a dispersant, for example, polyvinylpyrrolidine. Dilution with water gives a dispersion.

C) Emulsifiable concentrates (EC) 15 pests, by weight, of the active compounds in xylene were dissolved with incorporation of calcium dodecylbenzene sulfonate (Ca. DDB) and castor oil ethoxylate (in each case 5% concentration). Dilution with water delivers an emulsion.

D) Emulsions (ES) 40 pests, by weight, of the active compounds in xylene were dissolved with incorporation of calcium dodecylbenzene sulfonate and castor oil ethoxylate, (in each case with a concentration of 5%). This mixture was introduced into water by means of an emulsified (Ultraturax) and a homogeneous emulsion was manufactured. Dilution with water delivers an emulsion.

E) Suspensions (FS) In a stirred ball mill, 20 parts, by weight of active compounds with addition of dispersant, wetting agents and water or in organic solvent, were milled to deliver a fine suspension of the active compound. Dilution with water gives a stable suspension of the active compound.

F) Dispersible granules in water and water-soluble granules (WG, SG). 50 parts, by weight, of active compounds were finely ground with incorporation of dispersing and wetting agents, forming water-dispersible or water-soluble granules with the aid of technical apparatuses (for example, extruder, terre pulverizadora, fluidized bed). Dilution with water gives a stable description or solution of the active compound.

G) Dispersible powders in water and water soluble powders (SS, US). 75 parts, by weight, of the active compounds were milled in a rotor-stator mill with addition of dispersant, humectants and silica gel. The solution with water gives a stable dispersion or solution with the active compound. 2. Products to be applied without dilution H) Spreadable powders (DS). 5 parts, by weight, of the active compounds are finely divided. This delivers a spreadable or sprinkling product.

I) Granules (EX, FC, GG, MG) 0.5 parts, by weight, of the active compounds are finely ground and associated with 95.5% of vehicle or carrier materials. The methods used are extrusion; dried by spraying in the fluidized bed. This gives suitable granules by its application without dilution. The active ingredients can be used as such, in the form of their formulations or the forms of use prepared therefrom, for example, in the form of directly sprayable solutions, powders, gels, suspensions or dispersions, emulsions or dispersions, pests. , spreadable products in the form of powder, materials intended to be spread, or granules, microcapsules (CS), pellets or tablets, by spraying, atomising, spreading with powders, dusting or pouring or irrigation. The forms of use completely depend on the objectives sought; in each case the finest possible distribution of the active ingredients according to the invention is sought. Aqueous forms of use can be prepared from emulsion concentrates, pests or wettable powders (spreadable powders or dispersions) by incorporating water. To prepare emulsions, pastes or dispersions in oil, the substances, as such or dissolved in oil or in n solvent, can be homogenized in water by means of a wettable, tackifying, dispersing or emulsifying agent. Alternatively, it is possible to prepare concentrates composed of an active, wetting, adherent, dispersing or emulsifying substance and, if convenient, a solvent or oil, and such concentrates are suitable for dilution with water.

The concentrations of the active ingredient in the ready-to-use product may vary within relatively broad traits. In general, they are from 0.01 to 80%, preferably 0.1 to 50%. Different types of oils, humectants, adjuvants, fungicide herbicides, other pesticides or bactericides can be incorporated into the active ingredients, if this is convenient immediately before use. These agents are usually mixed with the agents according to the invention in a weight ratio of 1: 100 to 100: 1. The FS formulations are preferred. The preferred FS formulations of the compounds of the formula I for the treatment of the seed comprise from 0.5 to 80% of active ingredient, from 0.05 to 5% of humectant, from 0.5 to 15% of a dispersing agent , from 0.1 to 5% of a thickener, from 5 to 20% of an anti-freezing agent, give 0.1 to 2% of an anti-foaming agent, from 1 to 20% of an adhesive and / or a dye, from or up to 15%, of a tackifier / tackifier, from 0 up to 75% of a filler / vehicle and from 0.01 to 1% of a preservative. In the treatment of the seed, the application rates of the mixture are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 200 g. g per 100 kg of seed.

In the control of pests, the application of the compound of the formula (I) or the composition containing it is carried out by spraying or sprinkling the seeds or the soil (and thereby the seeds) after sowing. Another object of the invention is a method of treating the seed in the seed orifice with a granular formulation containing the active ingredient or a composition containing it, with optionally one or more solid or liquid vehicles acceptable in agriculture and / or optionally with one or more surfactants acceptable in agriculture. This method is advantageously used in cereal, maize, cotton and sunflower seed beds or marigolds for cereals and maize, dosages for compounds of formula I are between 50 and 500 g / ha. The invention also relates to the preparation product of the plants and especially the treated seed comprising it, that is, coated with and / or contained, in a compound of the formula I or a composition containing it. The expression "coated with and / or content" generally means that the active ingredient is mostly on the surface of the product's propagation at the time of application, although a greater or lesser part of the ingredient may penetrate into the product. the product of propagation, depending on the method of application. When said propagation product is replanted, it can absorb the active ingredient.

The seed contains the mixtures of the invention in an amount from 0.1 g to 10 kg per 100 kg of seed. The following list of pesticides can be used together with the compounds according to the invention, intended to illustrate the possible combinations, but does not always mean limitation: Organophosphates: Acephate, Azinphos-methyl, Chlorpyrifos, Chlorfenvinphos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Dysulfoton, Ethion, Fenitrothion, Fenthion Isoxathion, Malathion, Methamidophos, Methidathion, Methyl-Parathion, Mevinphos, Mono-crotophos, Oxydemeton-methyl, Paraoxon, Parathion, Phenthoate, Phosalone, Phosmet, Phosphamidon, Phorate, Phoxim, Pirimiphos -methyl, Profenofos, Prothiophos, Sulprophos, Terbufos, Triazop-hos, Trichlorfon; Carbamates: Alanycarb, Benfuracarb, Carbaryl, Carbosulfan, Fe-noxycarb, Furathiocarb, Indoxacarb, Me hiocarb, Methomyl, Oxa-yl, Pirimicarb, Propoxur, Thiodicarb, Triazamate; Pyrethroid: Bifenthrin, Cyfluthrin, Cypermethrin, alpha-Cypermethrin, Deltamethin, Esfenvalerate, Ethofenprox. , Fenpro-pathrin, Fenvalérate, Cyhalothrin, Lambda-Cyhalothrin, Permeth-rin, Silafluofen, Tau-fluvalinate, Tefluthrin, Zeta-Cypermethrin, - Arthropod growth regulators: a) inhibitors of chitin synthesis: benzoylureas: Chlorfluazuron , Difubenzuron, flucycloxuron, Flutenoxuron, Hexaflumuron, Lufenu- ron, Novaluron, Teflubenzuron, Triflumuron, Buprofezin, Diofelano, Hexythiazox, Etoxazole, Clofentazine; b) Ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) juvenoids: Pyriproxyfen, Methoprene, Phenoxycarb; d) inhibitors of lipid synthesis.

Neonicotinoids: Acetamiprid, Clothianidin, Flonicamid, Imidacloprid, Nitenpyram, Thiacloprid, ThiamethoxaM; Miscellaneous: Abamectin, Acequinocyl, Amitraz, Azadirachtin, Bifenazate, Gacillus thuringiensis, Bacillus subtilis, Cartap, Chlor-fenapyr, Chlordimeform, cyromazine, diafenthiuron, Dinetofuran, Diofenolan, Emamectin, Endosulfan, Ethiprole, Fenazaquin, Fi-pronil, Formetanate hydrochloride , Hydramethylnon, Indoxacarb, 4-. { (2Z) -2- ( { [4- (trifluoro-methoxy) anilino] carbonyl}. Hydrazono) -2- [3- (trifluoromethyl) phenyl} benzo-nitrile, pyridaben, pymetrocline, spinosad, sulfur, tebufenpyrad and thiocyclan.

In general, the term "pesticidally effective amount" means the amount of active ingredient required to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention and removal, destruction or reduction of another form of the occurrence and activity of a target organism the effective amount as a pesticide may vary for the different compounds / compositions used in the invention An effective pesticidal amount of the compositions will also vary according to the prevailing conditions, such as the desired pesticidal effect. and its duration, climate, target species, place, mode of application, and the like The pesticide effect of the compounds was demonstrated through the following experiences: Evaluation of the treatment of the seed of the root lom-briz corn, filamentous worm and corn seed Maggot Seeds protection against D larvae iabrotica undecimpunctata howardi, Agrio ti s lineatus (larvae), Delia platura (eggs): The active compounds were formulated in a solvent-surfactant vehicle consisting of 15% acetone and 0.05% Tween 20 (12 ™) (polyoxyethylene sorbitan monolaurate) in water Corn seeds ("Truckers Favorite" corn) were treated in batches of 50 by stirring with 450 microliters of the compound preparation in a glass jar and dried. The seeds were planted one per 120 ml container with air holes or vent in the sandy lid liquefied. Ten insect eggs or larvae were placed in each container. Mortality of eggs or larvae and feeding damage to roots and shoots was evaluated seven days after planting.

The percentage of insect mortality and feeding damage compared to the reference control with solvent-surfactant was calculated. For 251 g of active ingredient per 100 kg of seed, the compounds (1-1) and (1-2) provide more than 30% protection of the seed and shoot against feeding damage by the filamentous earthworm.

Claims (8)

1. A method of seed protection, CHARACTERIZED because it comprises contacting the seeds before sowing and / or after pre-germination with a compound of the formula I where W is chloro or trifluoromethyl, X and Y are each independently chloro or bromo; R 1 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, or C 3 -C 6 cycloalkyl, which may be substituted with 1 to 3 halogen atoms, or C 2 -C 4 alkyl, which is substituted by alkoxy -Ci ~ C4; R2 and R3 are Cx-C-alkyl; or they may be taken together to form C3-C3 cycloalkyl, which may be substituted by 1 to 3 halogen atoms or unsubstituted; R 4 is hydrogen or C 1 -C 3 alkyl; or the enantiomers or salts thereof, in effective amounts as a pesticide.

2. The method according to claim 1, CHARACTERIZED in that the compound of the formula I is applied in the amount from 0.1 g to 10 kg per 100 kg of seeds.

3. The method according to claim 1, CARAC¬ TERIZED because the compound of formula (I) is applied in an amount from 1 g to 2 g per 100 kg of seeds.

4. The method according to any of claims 1 to 3, characterized in that the compound of the formula (I) is a compound of the formula (1-1).

5. The method according to any one of claims 1 to 3, CHARACTERISTIC because the compound of the formula (I) is a compound of the formula (1-2).

6. A method for the protection of the seeds, CHARACTERIZED because the pests of the soil are of the order of Diptera, Lepidoptera, Coleoptera and Isoptera.

7. The use of the compounds of the formula I according to claim 1, 4 or 5, CHARACTERIZED because it is for the protection of the seeds against the pests at ground level.

8. Seed, CHARACTERI ADA because it comprises the compound of the formula I according to that defined in claims 1, 4 or 5 in an amount from 0.1 g to 10 kg per 100 kg of seed.