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
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B21/00—Nitrogen; Compounds thereof
  • C01B21/20—Nitrogen oxides; Oxyacids of nitrogen; Salts thereof
  • C01B21/24—Nitric oxide (NO)
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
  • B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
  • B01J19/087—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electric or magnetic energy
  • B01J19/088—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electric or magnetic energy giving rise to electric discharges
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B21/00—Nitrogen; Compounds thereof
  • C01B21/20—Nitrogen oxides; Oxyacids of nitrogen; Salts thereof
  • C01B21/203—Preparation of nitrogen oxides using a plasma or an electric discharge
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B21/00—Nitrogen; Compounds thereof
  • C01B21/20—Nitrogen oxides; Oxyacids of nitrogen; Salts thereof
  • C01B21/36—Nitrogen dioxide (NO2, N2O4)
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
  • C07D233/70—One oxygen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
  • C07D233/84—Sulfur atoms
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05H—PLASMA TECHNIQUE; PRODUCTION OF ACCELERATED ELECTRICALLY-CHARGED PARTICLES OR OF NEUTRONS; PRODUCTION OR ACCELERATION OF NEUTRAL MOLECULAR OR ATOMIC BEAMS
  • H05H1/00—Generating plasma; Handling plasma
  • H05H1/24—Generating plasma
  • H05H1/48—Generating plasma using an arc

Definitions

• the present invention relates to new imidazoline-ones or imidazoline-thiones compounds for phytosanitary use. It also relates to the processes for the preparation of said compounds and the products which may be used as intermediates in the preparation processes. It then relates to the use as fungicides of these compounds, the fungicidal compositions based on these compounds and methods for combating fungal diseases of crops using these compounds.
• An object of the present invention is to provide compounds with improved properties in the treatment of fungal diseases.
• Another object of the present invention is to provide compounds with a spectrum of use also improved in the field of fungal diseases.
• one of the 2 groups is different from H, or -an alkyl or haloal yl radical of 1 to 6 carbon atoms or -an alkoxyalkyl, al ylthioalkyl, alkylsulfonylalkyl, mono alkylaminoalkyl, alkenyl or alkynyl radical of 2 with 6 carbon atoms or
• an aryl radical comprising phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolinyl, isoquinolinyl, or methylenedioxyphenyl, optionally substituted with 1 to 3 groups chosen from R7 or
• arylalkyl an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical, the terms aryl and alkyl having the definitions given above or
• -RI and R2 can form, with the carbon to which they are linked on the ring, a carbocycle or a heterocycle having from 5 to 7 atoms, these rings being able to be fused with a phenyl, optionally substituted by 1 to 3 groups chosen from R7;
• -R3 represents: -the hydrogen atom or an alkyl group of 1 to 6 carbon atoms or
• alkoxyalkyl an alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, oxoalkyl, alkenyl or alkynyl group of 2 to 6 carbon atoms or
• N, N-dialkylcarbamoylalkyl group of 4 to 8 atoms; -R4 represents:
• n is equal to 1 or -an alkyl group of 1 to 6 carbon atoms or -an alkoxyalkyl, alkylthioalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, alkenyl or alkynyl group of 2 to 6 carbon atoms or -a dialkylaminoalkyl, alkoxycarbonylalkyl, or N- alkylcarbamoylalkyl group of 3 to 6 carbon atoms or
• -an N, N-dialkylcarbamoylalkyl group of 4 to 8 carbon atoms or -an aryl radical comprising phenyl, naphthyl, thienyl, furyl, pyridyl, imidazolyl, pyrazolyl, pyrrolyl, triazolyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl quinolinyl, isoquinolinyl, or methylene dioxyphenyl, optionally substituted with 1 to 3 groups chosen from R7 or
• arylalkyl an arylalkyl, aryloxy alkyl, arylthioalkyl or arylsulfonylalkyl radical, the terms aryl and alkyl having the definitions given above or
• thienylmethyl or urfuryl radical - a pyrrolidino, piperidino, morpholino or piperazino group optionally substituted with alkyl of 1 to 3 carbon atoms;
• R4 is H, or -an alkyl, haloalkyl, alkylsulfonyl, haloalkylsulfonyl radical of 1 to 6 carbon atoms or an alkoxyalkyl, alkylthioakyl, acyl, alkenyl, alkynyl, haloacyl, alkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkylsulfonyl, cyanoalkylsulfonyl radical of 2 to 6 carbon atoms or
• alkoxyalkoxycarbonyl alkylthioalkoxycarbonyl, cyanoalkoxycarbonyl radical of 3 to 6 carbon atoms or
• a cycloalkyl alkoxyacyl, alkylthioacyl, cyanoacyl, alkenylcarbonyl, alkynylcarbonyl radical of 3 to 6 carbon atoms or
• arylalkylcarbonyl especially phenylacetyl and phenyl propionyl
• arylcarbonyl especially benzoyl, optionally substituted with 1 to 3 groups from R7; thienylcarbonyl; furylcarbonyl; pyridylcarbonyl; benzyloxycarbonyl; furfuryloxycarbonyl; terrahydrofurfuryloxycarbonyl; thienylmethoxycarbonyl; pyridylmethoxycarbonyl; phenoxycarbonyl or phenylthiolcarbonyl, the phenyl itself being optionally substituted by 1 to 3 groups from R7; alkylthiolcarbonyl; haloalkylthiolcarbonyl; alkoxyalkylthiolcarbonyl; cyanoalkylthiolcarbonyl; benz
• -a sulfamoyl group optionally mono or disubstituted by -an alkyl or haloalkyl group of 1 to 6 carbon atoms or
• -R6 represents: -the hydrogen atom or
• an amino radical optionally mono or disubstituted by an alkyl or acyl radical of 1 to 6 carbon atoms or alkoxycarbonyl of 2 to 6 carbon atoms
• R4 is other than an optically residue active, derived from an optically active primary amine or an optically active amino acid.
• amino acid amides of formula II can be conventionally prepared by reacting an amine of formula R4NH2 with an amino acid ester of formula IU:
• Iminoesters IV can be obtained by reacting an amino acid ester III with an imidate of formula:
• the compounds of formula Ib can be obtained by alkylation of compounds Ib ', in which R2 is hydrogen, by a compound R2X in basic medium according to the method described in the Belgian patent application cited above:
• the reaction is catalyzed by acids.
• acids mineral acids, alkylsulfonic acids, arylsulfonic acids, acid resins, carboxylic acids can be used.
• the reaction can be carried out in aromatic solvents, halogenated hydrocarbons, ethers, cyclic ethers, esters, alcohols.
• hydrazides of formula VU can be prepared according to one of the methods described in the literature, for example:
• a preferred general access route analogous to point 2 above consists in activating the acid in the form of imidazoleQe (reaction a) or mixed anhydride (reaction b) to condense it with a hydrazine: at)
• Another preferred route for preparing the compounds of formula la consists in reacting a hydrazine R4NR5NH2 with an azalactone VI under certain conditions:
• reaction 1) by heating the reagents in an inert solvent in the presence of a acid to catalyze the reaction.
• a acid halogenated hydrocarbons, esters, aromatic solvents, alcohols can be used.
• mineral acids, alkylsulfonic acids, arylsulfonic acids, acid resins, carboxylic acids can be used.
• the reaction is carried out at a temperature of 50 to 150 ° C.
• Example 5 illustrates these conditions.
• R5 represents here an alkyl, alkoxycarbonyl, acyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, carbamoyl or sulfamoyl group, as defined above.
• X represents, a halogen, the sulfate group or an optionally substituted phenoxy, or an alkylsulfonyloxy or arylsulfonyloxy group, or a group R5O, when R5 is acyl.
• a base alkali hydrides, alcoholates or a tertiary amine can be used.
• the reaction can be carried out at a temperature between -30 ° C and + 50 ° C.
• solvent it is possible to use, for example, ethers, cyclic ethers, dimethylformamide, dimethylsulfoxide, aromatic solvents.
• the carbamoylation or thiocarbamoylation of the compounds (la 1 ) can be carried out by reaction with isocyanates or isothiocyanates according to the scheme:
• reaction is carried out under the same conditions as those described above, the base being able however to be used in catalytic amount.
• the reaction is carried out at a temperature between 10 and 100 ° C in the
• the intermediate aminohydrazides of formula VIII can be obtained according to a new process by reacting the hydrochloride of the acid chloride of the corresponding ⁇ -amino acid in the presence of a base according to the scheme:
• the reaction is carried out at a temperature between -20 ° and 40 ° C in the cyclic ethers or not.
• the nitrogenous organic bases such as triethylamine or pyridine can be used as the base.
• the intermediate acid chlorides can be obtained by the method described by S.LEVINE in J. Am. Chem. Soc. Of 1953, Volume: 76, page: 1392. They are then obtained by reacting the phosphorus pentachloride on the ⁇ -amino acid according to the diagram below:
• the preferred compounds for their better fungicidal activity and / or for their ease of synthesis are:
• R2 represents an alkyl group of 1 to 3 carbon atoms, preferably methyl
• R3 represents the hydrogen atom or an alkyl group of 1 to 3 carbon atoms, optionally substituted by one or more halogens, methoxy or methylthio.
• Example 1 This example illustrates the preparation of a hydrazide (VU) according to method B 4a): preparation of 2-propionylamino-2-phenyl-2 '-phenyl propionohydrazide (compound 102):
• Example 2 Preparation of a hydrazide (VII) according to method B 4b): phenyl hydrazide of N-trifluoroacetyl-2- (4-methyl phenyl) glycine:
• the contents of the first flask are quickly filtered on sintered glass in the Erlenmeyer flask containing phenylhydrazine. Let the mixture come back reaction at room temperature, washed with dilute soda, with water, then dried over MgSO4 before filtering and evaporating. 1.4 g (78% yield) are then obtained of a white solid with a melting point equal to 162 ° C. of formula:
• Example 3 This example illustrates the preparation of the compounds of formula la according to method B, by cyclization of compounds of formula VU: preparation of 2,4-dimethyl-4-phenyl-1-phenylamino-2-imidazoline-5-one (compound n ° 1).
• Example 4 preparation of a compound of formula la according to the method Cl °), 2,4-dimethyl-4-phenyl-1-phenylamino-2-imidazoline-5-one (compound n ° 1).
• a solution containing 0.9 g (4 mmol) of 2,4-dimethyl-4-phenyl-2-oxazoline-5-one, 0.43 g (4 mmol) of phenylhydrazine and 0, is heated at reflux for one hour.
• 1g of paratoluene sulfonic acid in 30 ml of toluene The water formed is removed by azeotropic entrainment and the medium is concentrated under reduced pressure.
• the crude product is then purified by chromatography on silica gel.
• Example 5 preparation of a compound of formula la according to the process C2 °): 2,4-dimethyl-4- (4-chlorophenyl) -1- (2-chlorophenylamino) -2-imidazoline-5-one (compound n ° 11).
• Example 7 In Vivo Test on Plasmopara Viticola (Downy Mildew): An aqueous suspension of the active ingredient to be tested is prepared, having the following composition:
• Tween 80 surfactant (oleate of polyoxyethylene derivative of sorbitan) diluted to 10% in water: 0.3 ml - make up to 60 ml of water.
• 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 culture of 4-5 days, then suspended at the rate of 100,000 units per cm 3 .
• 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.
• Example 8 In Vivo Test on Puccinia Recondita (Wheat Rust): An aqueous suspension of the active material 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.
• Wheat, in pots, sown on a 50/50 peat soil peat soil substrate, is treated at the 10 cm height stage by spraying the above aqueous suspension.
• an aqueous suspension of spores (100,000 sp / cm 3 ) 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.
• An aqueous suspension of the active ingredient to be tested having the following composition is prepared by fine grinding:
• Tomato plants (Marmande variety) are grown in pots. When these plants are one month old (5 to 6 leaf stage, height 12 to 15 cm), they are treated by spraying the above aqueous suspension and at various concentrations of the test compound.
• each plant is contaminated by spraying with an aqueous suspension of spores (30,000 sp / cm 3 ) of Phytophthora infestons.
• the tomato plants are incubated for 7 days at around 20 ° C in an atmosphere saturated with humidity.
• compositions which can be used as fungicidal agents, contain as active material one (or more) compound according to the invention as described above as a mixture with solid or liquid carriers, acceptable in agriculture and surfactants also acceptable in agriculture.
• the usual inert 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.
• the compositions according to the invention usually contain approximately 0.05 to 95% by weight of one (or more) compound according to the invention (hereinafter called active material), one or more solid supports or liquids 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 poly acrylic 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 amines fatty acids, substituted phenols (in particular alkylphenols or arylphenols), ester salts of sulfosuccinic acids, taurine derivatives (in particular alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols, esters of fatty acids and polyols, the sulfate, sulfonate and phosphate derivatives of the above compounds.
• the presence of at least one surfactant is generally essential when the compound and / or the inert support are not
• 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.
• solutions in particular water-soluble concentrates, emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, powders wettable (or spray powder), pastes, gels.
• the emulsifiable or soluble concentrates most often comprise 10 to 80% of active material, the emulsions or solutions ready for application containing, for their part, 0.001 to 20% of active material.
• emulsifiable concentrates can contain, when necessary, 2 to 20% of suitable additives such as stabilizers, surfactants, penetration agents, corrosion inhibitors, dyes or adhesives previously mentioned.
• emulsions with any desired concentration can be obtained by dilution with water, which are particularly suitable for application to crops.
• composition of some emulsifiable concentrates is the composition of some emulsifiable concentrates:
• Example CE 1 - active ingredient
• 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: some organic solids or mineral salts can be dissolved in the carrier 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, from 0 to 30% of a wetting agent, from 3 to 20% of a dispersing agent, and, when necessary,
• 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 this pasta are similar to wettable powders or spray 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.
• These dispersible granules of apparent density generally comprised between approximately 0.3 and 0.6 have a particle size generally comprised between approximately 150 and 2000 and preferably between 300 and 1500 microns.
• 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 depending on whether the selected filler is soluble or not in water.
• the filler When 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
• surfactants at a rate of 2 to 20% by weight of the granule
• at least one dispersing agent essentially anionic, such as an alkaline or alkaline earth polynaphthalene sulfonate or an alkaline or alkaline earth lignosulfonate, the remainder being nonionic or anionic wetting agents such as an alkaline or alkaline earth alkyl naphthalene sulfonate.
• other 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.
• 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
• 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 0.05 to 95% (by weight) of active substance.
• a subject of the invention is also the use of the compounds according to the invention for the fight against fungal diseases of plants by preventive or curative treatment of the latter or their place of growth.

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• Plasma & Fusion (AREA)
• Inorganic Chemistry (AREA)
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• Chemical Kinetics & Catalysis (AREA)
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• 1992
  • 1992-07-02 FR FR929208405A patent/FR2693192B1/fr not_active Expired - Fee Related
• 1993
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  • 1993-06-29 CA CA002139346A patent/CA2139346A1/fr not_active Abandoned
  • 1993-06-29 JP JP6503004A patent/JPH07508528A/ja active Pending
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  • 1993-07-01 TW TW082105236A patent/TW234076B/zh active
  • 1993-07-01 AP APAP/P/1993/000544A patent/AP496A/en active
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  • 1993-07-03 EG EG41193A patent/EG19984A/xx active
• 1994
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• 1995
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