Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D231/16—Halogen atoms or nitro radicals

Definitions

• the present invention relates to the use of 3-phenyl-pyrazole derivatives for the protection of plant propagating material against fungal diseases, the compositions containing these derivatives as well as new derivatives of this family, the compositions containing the latter and the fungicidal compositions. containing them as well as a process for the treatment of plants with these derivatives.
• Certain 3-phenyl-pyrazole derivatives are described in particular in published applications EP 0538 156 and WO 93/22287 for their advantageous properties against fungal diseases of the leaf parts of plants.
• plant propagating material is meant to designate all the generative parts of the plant that can be used for reproduction and multiplication thereof. Mention may be made, for example, of seeds (seeds in the narrow sense) for crops other than potatoes, roots, fruits, tubers, bulbs, rhizomes, parts of plants or even sprouted plants and young plants. seedlings, which must be transplanted after germination or after emergence from the soil. These young plants can be protected before transplantation by a total or partial treatment by immersion.
• multiplication products suitable for the treatment process according to the invention, preference will be given to:
• the seeds will be coated with 0.1 to 500 g of active material per quintal of seed, preferably 1 to 400 g per quintal.
• these are coated with an amount of active material corresponding to the soaking of said product in a composition containing 0.1 g / 1 to 100 g / 1 of active material.
• compositions for the treatment of plant propagating material against fungal diseases characterized in that they contain, as active materials, at least one 3-phenylpyrazole derivative of formula I:
• X ⁇ , X2, X3, X4 and X5, identical or different, are: - a hydrogen or halogen atom, a hydroxy, mercapto, cyano, thiocyanato, nitro, nitroso, amino group optionally substituted by one or two alkyls or phenyls,
• a phosphoryl group substituted by two groups chosen from the group comprising alkyl, alkoxy, alkylthio and dialkylamino, benzyloxy, phenyloxy or phenyl,
• two of the adjacent Xj, X2, X3, X4 and X5 can also form a bridge comprising from 2 to 4 members, at least one of which can be replaced by an oxygen atom.
• the carbons of this bridge may or may not be substituted by at least one halogen atom and / or at least one hydroxy, amino, alkyl, alkoxy .alkylthio, mono or di alkylamino, alkylsulfinyl or -sulfonyl or alkoxycarbonyl group, the alkyl part being as defined below, with the proviso that Xjà X5 cannot each be simultaneously a hydrogen atom;
• Y is a hydrogen, halogen, nitro, cyano, hydroxy, alkylcarbonyloxy, alkoxycarbonyloxy, aminocarbonyloxy, mercapto, carboxyl, carboxylate, formyl, alkyl (thio) carbonyl, arylcarbonyl, alkoxy (thio) carbony, carbamoyl atom
• cycloalkyl part may be substituted by the GR4 group, defined below,
• alkoxy optionally substituted by hydroxy, alkoxy, alkylthio, alkylsulfinyl or -sulfonyl,
• Z j is an oxygen or sulfur atom or an alkylamino or alkylimino or arylamino or arylimino group and
• - Z2 is: - a hydrogen, halogen atom, a hydroxy, mercapto, cyano, amino group, - alkyl, alkoxy, haloalkoxy, alkylthio, - alkenyl or alkynyl or alkenyloxy, each containing from 3 to 7 carbon atoms,
• the linear hydrocarbon part of these groups may comprise from 1 to 7 carbon atoms and may be optionally halogenated (from 1 to 8 halogen atoms),
• the cycloalkyl part of these groups can comprise from 3 to 7 carbon atoms and be optionally substituted by at least one substituent chosen from the group GR4 defined below,
• the phenyl part denotes the phenyl ring optionally substituted with 1 to 5 substituents chosen from the group comprising a halogen atom, an alkyl or alkoxy of 1 to 3 carbon atoms and nitro, - Het is a heterocyclic radical, mono or bicyclic, containing from 5 to 10 atoms, of which 4 are heteroatoms (oxygen, sulfur, nitrogen, phosphorus); the group GR4 comprises:
• alkyl alkoxy, alkylsulfenyl, alkylsulfonyl, alkycarbonyl, alkylthiocarbonyl, alkoxycarbonyl, alkoxythiocarbonyl, mono- or dialkykaminocarbonyl or mono- or dialkykaminothiocarbonyl, mono or dialkylaminosulfonyl, (the alkyl part of all these substituents containing from 1 to 4 carbon atoms and be substituted by 1 to 9 halogen atoms),
• formula IY is a chlorine or bromine atom.
• X1-X2 and X4 are a hydrogen or halogen atom or a nitro, amino or alkyl group, optionally halogen, of 1 to 4 carbon atoms.
• X3 is a hydrogen or fluorine atom.
• X ⁇ , X3 and X5 are a hydrogen atom and X2, X4 are each a chlorine atom b) X ⁇ is a nitro, X2, X4 are each a chlorine atom X3 is a fluorine atom and X5 is a hydrogen atom c) X ⁇ is a fluorine atom, X2, X4 are each a chlorine atom X3 is a fluorine atom, X3 and X5 are a hydrogen atom
• X ⁇ is a hydrogen or halogen atom or a nitro, amino or methyl group
• X2 is a halogen atom or a nitro, amino or methyl group
• X3 is a hydrogen or halogen atom
• X4 is a halogen atom or an amino nitro or methyl group
• X5 is a hydrogen or halogen atom
• New preferred derivatives are as in formula I: Y , Z, X ⁇ and X4 are as described above,
• X2 is a chlorine or bromine atom
• X3 and X5, identical or different, are each a hydrogen or fluorine atom.
• the derivatives according to the invention can be prepared according to methods known per se as described in published applications EP 0 538 156 and WO 93/22287.
• the following examples respectively illustrate the preparation of new derivatives, their physicochemical characteristics (the structures have been verified by NMR analysis), their fungicidal properties in treatment for leaf diseases as well as the fungicidal properties in seed treatment of all of the derivatives according to the invention.
• Example 1 Benzoic acids. a) 2,3-Dichloro 5-nitro benzoic acid.
• aqueous phase is acidified with IN HCl, extracted with ether.
• the organic phase is dried over magnesium sulfate, concentrated in vacuo.
• the solid is recrystallized from a heptane / ether mixture (yield: 54%; melting point 136 ° C).
• aqueous phase is acidified with IN HCl, extracted with ether.
• the organic phase is dried over magnesium sulfate, concentrated in vacuo.
• the solid is recrystallized from a heptane / ether mixture (yield: 37%; melting point: 177 ° C). f) 3,5-Dichloro-2,6-difluorobenzoic acid.
• Example 2 Acetophenones. (see EXAMPLE 4 D of application WO 93/22287)
• acetophenones are obtained from the benzoic acids previously obtained according to the following procedure: a) 2,3-dibromo-5-methyl benzoic acid chloride.
• This solution is poured dropwise onto a solution of 28.5 g (0.48 mole) of acetaldoxime, 25.0 g (0.10 mole) of copper sulphate pentahydrate, of 20.5 g (0.018 mole) of anhydrous sodium sulfite and 121 g (1.50 mole) of sodium acetate in 250 ml of water maintained at 15 ° C. After 1 hour of stirring, the medium is acidified by adding concentrated hydrochloric acid.
• Example 5 3-methvl-4-fluoro-5-chloro acetophenone 16.7 g (0.123 mol) of aluminum chloride are loaded into 100 ml of 1,2-dichloroethane. The whole is cooled to + 10 ° C. and 8.2 ml of acetyl chloride are added.
• Example 6 Enaminones (cf. Examples 5 and 6 of the application WO 93/22287) 1 - (3,5-dichlorophenyl) -3-dimethylaminopropen-2-one- 1:
• Example 7 Chloroenaminones. 1- (3,5-dimethyl-4-fluorophenyl) -2-chloro-3-dimethylamino-2-propene-1-one. A suspension of 6.0 g (0.03 mole) of 2-chloro-3 ', 5'-dimethyl-4'-fluoroacetophenone in a mixture of 7.15 g (0.06 mole) of dimethylformamide dimethylacetal and 100 ml of heptane is brought to 50 ° C. and then stirred at this temperature for 8 h. After cooling, the reaction medium is filtered and the crystals obtained washed with heptane and then dried (3.2 g).
• Example 8 ÎH-Pyrazoles (see Example 7 of application WO 93/22287) 3- (3,5-dichlorophenyl) 1H-pyrazole.
• Example 10 3- (2-amino> phenyl-4-chloro pvrazoles (see Example 14 of application WO 93/22287) 3- (2-amino-3,5-dichloro) phenyl-4-chloro pyrazole (compound 19 )
• Example 11 4-chloro pvrazoles (Example 15 of application WO 93/22287). 3- (2-methvlthio-3.5-dichloro ') phenvl-4-chloro pyrazole (compound 251
• This compound is obtained by diazotization of 3- (2-amino-3,5-dichlorophenyl) -4-chloro pyrazole and reaction with dimethyldisulfide, according to the methods described in the literature: Yield 30%; honey.
• Example 12 3- (2-Nitro1phenv1-4-chloro-pvrazoles 3- (2-nitro-3,5-dichloro-4-fluoro phenyl) -4-chloro pyrazole (compound 30). 0.43 ml (0.0104 mole) fuming nitric acid (100%) to a solution cooled to about +5 ° C (ice water bath) of 2.50 g (0.00943 mole) of 3- (3,5-dichloro-4-fluorophenyl) -4-chloro pyrazole (prepared according to the process described in patent WO 9322287, compound 266) in 25 ml of 100% sulfuric acid The reaction medium is stirred cold for 20 minutes then at room temperature for one hour and finally poured over 150 g of ice The precipitate formed is extracted with 150 ml of ethyl acetate The solution obtained is washed with 100 ml of water, 100 ml of a solution saturated with sodium hydrogencarbonate, 100 ml of water,
• Example 13 3- (5-fluorophenylV4-chloropyrazoles 3- (2,3-dichloro5-fluoro phenyl) 4-chloro pyrazole (compound 35).
• 3- (5-amino-2,3-dichlorophenyl) -4-chloropyrazole diazonium tetrafluoroborate is obtained by pouring an aqueous solution of sodium nitrite (0.0021 mol) dropwise at 0 ° C on a solution containing 0.002 mol of 3- (5-amino-2,3-dichlorophenyl) -4-chloro-pyrazole and 5 ml of tetrafluoroboric acid in 50% aqueous solution.
• the reaction medium is thus stirred at 0 ° C for 1 hour then poured into 50 ml of water and of ice.
• the precipitate obtained is dried quickly under vacuum and then thermally decomposed to dryness at 145 ° C.
• Example 14 3- (3-chloro 5-hvdroxv phenvll 4-chloro pyrazole (control derivative Al)
• 4-chloro-3- (3,5- dichlorophenyl) pyrazole prepared as described in Example 9 of application WO 9322287
• NMP N-methyl-pyrroidone
• 43.2 g (0.8 mole) of sodium methylate are added. and the whole is heated at 140 ° C. for 50 hours. After cooling, the reaction mixture is poured into 500 ml of water, acidified and then extracted with ethyl acetate.
• Example 15 3- (3-chloro 5-fluoro phenyll 4-chloro pyrazole (compound 371.
• Example 16 N-SUBSTITUTED PYRAZOLES (Example 19D of application WO 93/22287).
• Example 17 4-chloro-3- (5-chloro-3-cyano-2-fluorophenyl1 pyrazole (compound 621.
• Example 22 Metal complex of 4-chloro-3- (3.5-dichlorophenvl1pvrazole and copper chloride (compound 74 1.
• the present invention also relates to a process for the treatment of cultivated plants affected or liable to be affected by fungal diseases, characterized in that an effective dose of a compound according to the formula ( I).
• effective dose is meant an amount sufficient to allow the control and destruction of the fungi present on these cultivated plants.
• the doses of use can however vary within wide limits according to the fungus to be combated, the type of culture, the climatic conditions, and according to the compound used.
• the compounds are advantageously applied in doses of 0.1 to 500 g of active material per quintal of seed, and preferably 1 to 400 g / quintal.
• fungal diseases diseases caused by phytopathogenic fungi, in particular those of the family of oomycetes, ascomycetes and basidiomycetes.
• crops which can be the subject of a fungicidal treatment using a compound according to the invention mention may be made of rice, cereals, in particular wheat and barley, as well as vegetable plants.
• Rice is a preferred crop for fungicide treatments using a compound according to the invention.
• 30 g of seeds are treated in a HEGE bowl with active ingredients according to the invention in the form of concentrated aqueous suspensions, at a concentration of 1.5 liters per quintal.
• 30 seeds are sown in pots (7x7x8 cm) on pozzolan peat substrate and 3 pots are produced by treatment.
• a contaminated untreated control and an uncontaminated control are sown under the same conditions.
• the healthy seeds treated are sown and a suspension of spores is provided at the rate of 10 ml of aqueous suspension per pot.
• the concentration of the suspension varies depending on the pathogen studied:
• the pots are placed in a climatic chamber at 5 ° C with saturated humidity, during a period which depends on the test carried out, namely 3 weeks for Drechslera graminea / Drechslera teres and Cochliobolus sativus and 2 weeks for Fusarium culmorum / Fusarium nivale / Septoria nodorum).
• the pots are then transferred to a climatic chamber at 10 ° C (photoperiod: 8 a.m. day; 4 p.m. night), relative humidity of 80%, until symptoms are expressed.
• the scoring is done visually in comparison with the contaminated untreated control.
• Drechslera graminea with the following derivatives: 3, 4, 5, 7, 10, 18, 26, 30, 68, 69;
• Drechslera teres with the following derivatives: 3, 26, 30, 82, 83, 84;
• - on Cochliobolus sativus with the following derivatives: 3, 26, 30;
• the present invention also relates to a method of treating cultivated plants affected or likely to be affected by fungal diseases, characterized in that an effective dose of a new compound of formula (I) is applied to the aerial parts of these plants. ) as defined above.
• effective dose is meant an amount sufficient to allow the control or destruction of the fungi present on these cultivated plants.
• the doses of use can however vary within wide limits according to the fungus to be combated, the type of culture, the climatic conditions, and according to the compound used.
• the compounds are advantageously applied at doses of 0.002 to 5 kg / ha, and preferably from 0.005 to 1 kg / ha.
• fungal diseases diseases caused by phytopathogenic fungi, in particular those of the family of oomycetes, ascomycetes and basidiomycetes.
• crops which can be the subject of a fungicidal treatment using a compound according to the invention mention may be made of rice, cereals, in particular wheat and barley, as well as vegetable plants.
• Rice is a preferred crop for fungicide treatments using a compound according to the invention.
• Example 24 In vivo test on Botrvtis cinere ⁇ on excised tomato leaf: (sensitive strains and strains resistant to benzimidazolesl:
• An aqueous suspension of the active ingredient to be tested having the following composition is prepared by fine grinding:
• - active ingredient 60 mg - surfactant Tween 80, oleate of polyoxyethylene derivative of sorbitan) diluted to
• aqueous suspension is then diluted with water to obtain the desired concentration of active material.
• Tomatoes grown in a greenhouse (Marmande variety) 30 days old are treated by spraying with aqueous suspensions as defined above and at various concentrations of the test compound. After 24 hours the leaves are cut and put in a Petri dish (diameter 14 cm), the bottom of which has been previously lined with a disc of wet filter paper (10 leaflets per box).
• the inoculum is then brought using a syringe by depositing drops (3 per leaflet) of a suspension of Botrytis cinerea spores, sensitive to benzimidazoles or resistant to benzimidazoles, obtained from 15-day cultures, then suspended at a rate of 150,000 units per cn_3.
• the control is made 6 days after the contamination in comparison with an untreated control. Under these conditions, at the dose of 1 g / 1, good (at least 75%) or total protection is observed with the following compounds: 1, 2, 3, 4, 5, 6, 7, 9, 10, 12, 13, 19, 20, 21, 26, 27, 28, 30, 31, 32, 33, 34, 35, 36, 37, 39, 40, 62, 68, 70, 74, 75, 76, 77, 78, 79, 80, 81 on Botrytis sensitive to benzimidazoles.
• An aqueous suspension of the active ingredient to be tested having the following composition is prepared by fine grinding:
• This aqueous suspension is then diluted with water to obtain the desired concentration of active material.
• Rice, sown in pots in a 50/50 mixture of enriched peat and pozzolan, is treated at the 10 cm height stage by spraying the above aqueous suspension.
• an aqueous suspension of spores of Pyricularia oryzae obtained from a 15-day culture, is applied to the leaves, then suspended at the rate of 100,000 units per cm 2.
• the rice plants are placed for 24 hours in incubation (25 ° C, 100% relative humidity), then placed in an observation cell, under the same conditions, for 5 days.
• An aqueous suspension of the active ingredient to be tested having the following composition is prepared by fine grinding:
• - active ingredient 60 mg - surfactant Tween 80, oleate of polyoxyethylene derivative of sorbitan) diluted to
• This aqueous suspension is then diluted with water to obtain the desired concentration of active material.
• Vine cuttings (Vitis vinifera). Chardonnay variety, are grown in pots. When these plants are 2 months old (8 to 10 leaf stage, 10 to 15 cm high), they are treated by spraying with the above aqueous suspension. Plants, used as controls are treated with an aqueous solution not containing the active ingredient.
• each plant After drying for 24 hours, each plant is contaminated by spraying with an aqueous suspension of Plasmopara viticola spores obtained from a 7-day culture, then suspended at the rate of 100,000 units per cm 2.
• the contaminated plants are then incubated for two days at approximately 18 ° C, in an atmosphere saturated with humidity and then for 5 days at approximately 20-22 ° C under 90-100% relative humidity.
• the reading is done 7 days after contamination, in comparison with the control plants.
• An aqueous suspension of the active ingredient to be tested having the following composition is prepared by fine grinding:
• an aqueous suspension of spores (100,000 sp / cm ⁇ ) is sprayed onto the wheat; this suspension was obtained from contaminated plants.
• the wheat is then placed for 24 hours in an incubation cell at approximately 20 ° C. and at 100% relative humidity, then for 7 to 14 days at 60% relative humidity.
• the condition of the plants is checked between the 8th and 15th day after contamination, by comparison with an untreated control.
• the present invention also relates to compositions, usable as fungicidal agents, containing as active material (s) one (or more) compound according to formula (I) as described above, in admixture with solid or liquid carriers , acceptable in agriculture and surfactants also acceptable in agriculture.
• active material s
• one (or more) compound according to formula (I) as described above
• solid or liquid carriers acceptable in agriculture and surfactants also acceptable in agriculture.
• the inert and usual supports and the usual surfactants can be used.
• compositions can also contain all kinds of other ingredients such as, for example, protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilizers, sequestrants, etc. More generally the compounds used in the invention can be combined with all the solid or liquid additives corresponding to the usual techniques of formulation.
• compositions according to the invention usually contain from 0.05 to 95% approximately (by weight) of a compound according to the invention (hereinafter called active material), one or more solid or liquid carriers and, optionally, one or more surfactants.
• support in the present description, is meant an organic or mineral, natural or synthetic material, with which the compound is combined to facilitate its application to the plant, to seeds or to the soil.
• This support is therefore generally inert and it must be acceptable in agriculture, in particular on the treated plant.
• the support can be solid (clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.) or liquid (water, alcohols, in particular butanol etc.).
• the surfactant can be an emulsifying, dispersing or wetting agent of ionic or nonionic type or a mixture of such surfactants. Mention may be made, for example, of salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulfonic or naphthalene sulfonic acids, polycondensates of ethylene oxide on fatty alcohols or on fatty acids or on fatty amines , substituted phenols (in particular alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (in particular alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols, esters of fatty acids and of polyols, the derivatives containing sulfates, sulfonates and phosphates of the preceding compounds.
• the presence of at least one surfactant is generally essential when the compound and / or the in
• compositions for agricultural use according to the invention can contain the active materials according to the invention within very wide limits, ranging from 0.05% to 95% (by weight).
• Their content of surfactant is advantageously between 5% and 40% by weight.
• compositions according to the invention are themselves in fairly diverse forms, solid or liquid.
• dusting powders with compound content of up to 100%
• granules in particular those obtained by extrusion, by compacting, by impregnation of a granulated support, by from a powder (the compound content in these granules being between 0.5 and 80% for the latter cases), the effervescent tablets or tablets.
• the compounds of formula (I) can also be used in the form of powders for dusting; one can also use a composition comprising 50 g of active material and 950 g of talc; one can also use a composition comprising 20 g of active material, 10 g of finely divided silica and 970 g of talc; these constituents are mixed and ground and the mixture is applied by dusting.
• liquid compositions or intended to constitute liquid compositions during application, mention may be made of solutions, in particular water-soluble concentrates, emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, powders wettable (or spray powder), pastes, gels.
• Emulsifiable or soluble concentrates most often include 10 to 80
• the emulsions or solutions ready for application containing, for their part, 0.001 to 20% of active material.
• the emulsifiable concentrates can contain, when necessary, 2 to 20% of suitable additives such as stabilizers, surfactants, penetration agents, corrosion inhibitors, dyes or adhesives previously cited. From these concentrates, emulsions with any desired concentration can be obtained by dilution with water, which are particularly suitable for application to crops.
• suitable additives such as stabilizers, surfactants, penetration agents, corrosion inhibitors, dyes or adhesives previously cited.
• composition of some emulsifiable concentrates is the composition of some emulsifiable concentrates:
• the concentrated suspensions are prepared so as to obtain a stable fluid product which does not deposit and they usually contain from 10 to 75% of active material, from 0.5 to 15% of surfactants, from 0 , 1 to 10% of thixotropic agents, 0 to 10% of suitable additives, such as defoamers, corrosion inhibitors, stabilizers, penetrating agents and adhesives and, as support, water or an organic liquid in which the active ingredient is sparingly or not very soluble: certain organic solids or mineral salts can be dissolved in the support to help prevent sedimentation or as antifreeze for water.
• Wettable powders are usually prepared so that they contain 20 to 95% of active ingredient, and they usually contain, in addition to the solid support, 0 to 30% of a wetting agent, 3 20% of a dispersing agent, and, when necessary, 0.1 to 10% of one or more stabilizers and / or other additives, such as penetrating agents, adhesives, or anti-caking agents, dyes, etc.
• the active ingredients are intimately mixed in the appropriate mixers with the additional substances and ground with mills or other suitable grinders.
• pasta can be made.
• the conditions and methods of making and using these pastes are similar to those of wettable powders or spraying powders.
• compositions of wettable powders As an example, here are various compositions of wettable powders (or spraying powders):
• Example PM 3 This wettable powder contains the same ingredients as in the previous example, in the following proportions:
• aqueous dispersions and emulsions for example the compositions obtained by diluting with water a wettable powder or an emulsifiable concentrate according to the invention, are included in the general scope of the present invention.
• the emulsions can be of the water-in-oil or oil-in-water type and they can have a thick consistency like that of a "mayonnaise".
• the compounds according to the invention can be formulated in the form of water-dispersible granules also included within the scope of the invention.
• the active material content of these granules is generally between approximately 1% and 90%, and preferably between 25% and 90%.
• the rest of the granule is essentially composed of a solid filler and optionally surfactant additives giving the granule properties of dispersibility in water.
• These granules can be essentially of two distinct types 30
• the filler is water-soluble, it can be mineral or, preferably, organic. Excellent results have been obtained with urea.
• an insoluble filler it is preferably mineral, such as for example kaolin or bentonite.
• surfactants at a rate of 2 to 20% by weight of the granule
• at least one dispersing agent essentially anionic, such as a polynaphthalene alkali or alkaline earth sulfonate or an alkaline or alkaline earth lignosulfonate, the remainder being nonionic or anionic wetting agents such as an alkali or alkaline earth alkyl naphthalene sulfonate.
• anionic such as a polynaphthalene alkali or alkaline earth sulfonate or an alkaline or alkaline earth lignosulfonate
• nonionic or anionic wetting agents such as an alkali or alkaline earth alkyl naphthalene sulfonate.
• adjuvants can be added such as anti-foaming agents.
• the granule according to the invention can be prepared by mixing the necessary ingredients and then granulation according to several techniques known per se (bezel, fluid bed, atomizer, extrusion, etc.). It generally ends with a crushing followed by sieving to the particle size chosen within the limits mentioned above. Can also be used granules obtained as above and then impregnated with a composition containing the active material.
• Example GDI Dispersible granules
• a mixer 90% by weight of active material and 10% urea pearls are mixed. The mixture is then ground in a pin mill. A powder is obtained which is moistened with approximately 8% by weight of water. The wet powder is extruded in a perforated roller extruder. A granule is obtained which is dried, then crushed and sieved, so as to keep respectively only the granules of a size between 150 and 2000 microns.
• Example GD2 Dispersible granules In a mixer, the following constituents are mixed:
• This mixture is granulated in a fluid bed, in the presence of water, then dried, crushed and sieved so as to obtain granules of size between 0.15 and 0.80 mm.
• These granules can be used alone, in solution or dispersion in water so as to obtain the desired dose. They can also be used to prepare combinations with other active materials, in particular fungicides, the latter being in the form of wettable powders, or aqueous granules or suspensions.
• compositions suitable for storage and transport they more advantageously contain from 0.5 to 95% (by weight) of active substance.

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