WO2006087343A1 - Pyrazolcarbonsäureanilide, verfahren zu ihrer herstellung und sie enthaltende mittel zur bekämpfung von schadpilzen - Google Patents
Pyrazolcarbonsäureanilide, verfahren zu ihrer herstellung und sie enthaltende mittel zur bekämpfung von schadpilzen Download PDFInfo
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- WO2006087343A1 WO2006087343A1 PCT/EP2006/050962 EP2006050962W WO2006087343A1 WO 2006087343 A1 WO2006087343 A1 WO 2006087343A1 EP 2006050962 W EP2006050962 W EP 2006050962W WO 2006087343 A1 WO2006087343 A1 WO 2006087343A1
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- Prior art keywords
- methyl
- carboxylic acid
- pyrazole
- amide
- dichlorobiphenyl
- Prior art date
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- 0 CC(C)(c1c(*)[n](C)nc1*)O Chemical compound CC(C)(c1c(*)[n](C)nc1*)O 0.000 description 2
Classifications
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- 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
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- 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
Definitions
- Pyrazolecarboxylic acid anilides process for their preparation and compositions containing them for controlling harmful fungi
- the present invention relates to pyrazolecarboxanilides of the formula I.
- n zero or 2; m 2 or 3;
- X 1 is fluorine or chlorine; X 2 is halogen;
- Y is CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 haloalkyl, methoxy or methylthio; p is zero or 1;
- R 1 is fluorine, chlorine, bromine, C 1 -C 4 -A ⁇ yI or C r C 4 haloalkyl
- R 2 is hydrogen or halogen
- R 3 is hydrogen, methyl or ethyl
- the substituents X 1 and X 2 may independently of one another have different meanings in the case of multiple substitution.
- the invention relates to processes for the preparation of these compounds, compositions containing them and methods for their use for controlling harmful fungi, in particular Botrytis.
- Pyrazolcarbonklareanilide be known with fungicidal activity.
- EP-A 545 099 and EP-A 589 301 describe biphenylanilides of this type which have monosubstitution on the biphenyl group.
- iodopyrazolecarboxanilides which differ from the present compounds I in particular by an iodine substituent instead of R 1 .
- the object of the present invention was to find Pyrazolcarbonklareanilide with improved fungicidal activity than the compounds of the prior art. Accordingly, the compounds I defined above were found. In addition, there have been found processes for preparing these compounds, compositions containing them and methods of using them to control harmful fungi.
- the compounds of the formula I have an over the known compounds improved activity against harmful fungi.
- the compounds of the formula I can be present in various crystal modifications which may differ in their biological activity. They are also the subject of the present invention.
- halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;
- C 1 -C 4 -alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl, preferably methyl or ethyl;
- C 1 -C 4 -haloalkyl represents a partially or completely halogenated C 1 -C 4 -alkyl radical, where the halogen atom (s) is / are in particular fluorine and / or chlorine, ie, for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, diflu - ormethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloro-2-fluoroethyl, 2,2,2-trifluoroethyl, 2 Chloro-1,1,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2-bromo-2,2-difluoroethy
- the compounds I are generally obtained by reacting a carboxylic acid halide of the formula II in a manner known per se (for example, March, Advanced Organic Chemistry, 2nd Ed., 382 f., McGraw-Hill, 1977) in the presence of a Base reacted with an aniline of formula III:
- the radical Hal in the formula II represents a halogen atom such as fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine or bromine.
- This reaction is usually carried out at temperatures of (-2O) 0 C to 100 0 C, preferably 0 ° C to 50 0 C.
- Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and methylene chloride, dimethylsul
- Suitable bases are generally inorganic compounds, for example alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride , Alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and alkali metal hydrogen carbonates such as sodium bicarbonate and organometallic compounds, in particular alkali metal.
- alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide
- alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide
- lalkyle such as methyllithium, butyllithium and phenyllithium
- alkylmagnesium halides such as methylmagnesium chloride and alkali metal and alkaline earth metal alkoxides such as sodium, sodium, potassium, potassium tert-butoxide and Dimethoxymagnesium also organic bases, eg. B.
- tertiary amines such as trimethylamine, triethylamine, di-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration.
- Triethylamine and pyridine are particularly preferably used.
- the bases are generally used in equimolar amounts based on the compound II. But they can also be used in an excess of 5 mol% to 30 mol%, preferably 5 mol% to 10 mol%, or - in the case of using tertiary amines - optionally as a solvent.
- the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use II in an excess of 1 mol% to 20 mol%, preferably 1 mol% to 10 mol%, based on III.
- Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide and dimethylformamide, more preferably methylene chloride, toluene and tetrahydrofuran.
- aromatic hydrocarbons such as toluene,
- Suitable dehydrating agents are 1, 1'-carbonyldiimidazole, bis (2-oxo-3-oxazolidinyl) phosphoryl chloride, carbodiimides such as N, N'-dicyclohexylcarbodiimide and N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide, phosphonium salts such as (benzotriazole-1 - yloxy) tris (dimethylamino) phosphonium hexafluorophosphate, bromotripyrrolidinophosphonium hexafluorophosphate, bromotris (dimethylamino) phosphonium hexafluorophosphate and chlorotripyrrolidinophosphonium hexafluorophosphate, uronium and thiuronium salts such as O- (benzotriazol-1-yl) -N, N, N ', N'-te
- Suitable organic bases are tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines. Triethylamine and pyridine are particularly preferably used.
- the bases are generally used in excess of 10 mol% to 200 mol%, preferably from 50 mol% to 150 mol% based on the compound IV.
- the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use one of the compounds in an excess of 1 mol% to 20 mol%, preferably 1 mol% to 10 mol%.
- the de- Hydrating agents are generally used in excess of from 5 mol% to 100 mol%, preferably from 5 mol% to 60 mol%.
- Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,
- Cyclohexane and petroleum ether aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, and dimethyl sulfoxide and dimethylformamide, particularly preferred diethyl ether, tert-butyl methyl ether, tetrahydrofuran and dimethylformamide.
- aromatic hydrocarbons such as toluene, o-, m- and p-xylene
- halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene
- ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, diox
- Suitable alkylating agents are alkyl halides such as methyl iodide, ethyl iodide, methyl bromide, ethyl bromide, methyl chloride and ethyl chloride, alkyl (perfluoroalkyl sulfonates) such as methyl trifluoromethyl sulfonate and ethyl trifluoromethyl sulfonate, alkyl (alkyl sulfonates) such as methyl methyl sulfonate and ethyl methyl sulfonate, Al kyl (arylsulfonates) such as methyl p-tolylsulfonate and ethyl p-tolylsulfonate, oxonium salts such as trimethyloxonium tetrafluoroborate and triethyloxonium tetrafluoroborate.
- alkyl halides such as methyl
- methyl iodide ethyl iodide
- methyl bromide ethyl bromide
- chloride methyl chloride
- ethyl chloride ethyl chloride
- the bases used are generally inorganic compounds, for example alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide.
- sodium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide
- alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride
- alkali metal amides such as lithium amide, sodium amide and potassium amide
- alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate , Potassium carbonate and calcium carbonate
- alkali metal hydrogen carbonates such as sodium bicarbonate or organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyl lithium and phenyl lithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal and Erdalkalimetallalko
- the bases are generally used in equimolar amounts based on the compound I. However, they can also be used in an excess of 5 mol% to 30 mol%, preferably 5 mol% to 10 mol%.
- the starting materials are generally reacted in approximately equimolar amounts with one another. However, it may also be advantageous for the yield to use the alkylating agent in an excess of 1 mol% to 20 mol%, preferably 1 mol% to 10 mol%, based on I.
- n zero; m 3; X 1 chlorine; X 2 is fluorine or chlorine, preferably fluorine;
- Trifluoromethyl especially difluoromethyl or trifluoromethyl; most preferably difluoromethyl;
- R 2 is hydrogen, fluorine or chlorine, in particular hydrogen or chlorine, particularly preferably hydrogen;
- R 3 is hydrogen or methyl, in particular hydrogen; W oxygen.
- radicals X 2 are preferably in the 2,4,5- or 3,4,5-position, in particular in the 3,4,5-position.
- X 2 is fluorine or chlorine; Y is methyl, difluoromethyl, trifluoromethyl or methoxy;
- R 1 is F, chloro, methyl, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl;
- R 2 is hydrogen, fluorine or chlorine
- R 3 is hydrogen or methyl; W oxygen.
- X 2 is fluorine or chlorine; n zero; p zero;
- R 1 is F, chlorine, methyl, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl, in particular fluorine, chlorine, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or th-fluoromethyl;
- R 2 is hydrogen, fluorine or chlorine
- R 3 is hydrogen
- radicals X are preferably in the 2,4- or 3,4-position, in particular in the 3,4-position.
- Table 2 Compounds of the general formula IA in which R 2 is Cl, R 3 is hydrogen and R 1 and B for each individual compound correspond in each case to one row of Table A.
- Table 7 Compounds of the general formula IC in which B for each individual compound corresponds in each case to one row of Table B.
- Table 8 Compounds of the general formula I-D, wherein B for each individual compound corresponds in each case to one row of Table B.
- the compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Peronosporomyces (syn. Oomycetes) and Basidiomycetes. They are sometimes systemically effective and can be used in crop protection as foliar, soil and Beizfungizide.
- Alternaria species on vegetables, oilseed rape, sugar beets and fruits and rice for example A. solani or A. alternata on potato and other plants
- Bipolaris and Drechslera species on maize, cereals, rice and turf e.g., D. teres on barley, D. tritci-repentis on wheat
- Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines, Bremia lactucae on lettuce, - Cercospora species on maize, soybeans, rice and sugar beet (for example C. beticula on sugar beet),
- Cochliobolus species on corn, cereals, rice e.g., Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice
- Colletotricum species on soybeans e.g., C. acutatum on various plants
- Gibberella species on cereals and rice eg Gibberella fujikuroi on rice
- Grainstaining complex on rice Helminthospohum species (eg H. graminicola) on corn and rice,
- Mycosphaerella species on cereals, bananas and peanuts (M. graminicola)
- Pseudoperonospora species on hops and cucurbits e.g., P. cubenis
- Puccinia species on cereals, maize and asparagus P. triticina and P. striformis on wheat, P. aspa ragi on asparagus
- Rhizoctonia species e.g., R. solani
- Rapeseed, potatoes, sugar beet, vegetables and other plants are Rapeseed, potatoes, sugar beet, vegetables and other plants.
- Sclerotinia species e.g., S. sclerotiorum
- oilseed rape e.g., sunflowers and other plants
- Venturia species scab
- pear e.g., V. inaequalis on apple
- the compounds I are also suitable for controlling harmful fungi in the protection of materials (eg wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
- harmful fungi ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sciophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleu- rotus spp., Poria spp., Serpula spp.
- Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
- the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
- the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
- the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
- the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
- seed treatment e.g. by dusting, coating or impregnating seed
- amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg, of seed are required.
- the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
- the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
- the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
- the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
- Suitable solvents / auxiliaries are essentially:
- aromatic solvents eg Solvesso products, xylene
- paraffins eg petroleum fractions
- alcohols eg methanol, butanol, pentanol, benzyl alcohol
- ketones eg cyclohexanone, gamma-butyrolactone
- pyrrolidones NMP, NOP
- Acetates glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
- solvent mixtures can also be used
- - Carriers such as ground natural minerals (eg kaolins, clays, talc, chalk) and ground synthetic minerals (eg fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene) Fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
- ground natural minerals eg kaolins, clays, talc, chalk
- ground synthetic minerals eg fumed silica, silicates
- Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene) Fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin liquors and methylcellulose.
- the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
- mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
- mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivative
- Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
- Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
- Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell meal, cellulose powder and other solid carriers.
- Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics
- Seed treatment formulations may additionally contain binders and / or gelling agents and optionally dyes.
- Binders can be added to increase adhesion of the active ingredients to the seed after treatment.
- Suitable binders are, for example, EO / PO block copolymer surfactants, but also polyvinyl alcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrenes, polyethyleneamines, Polyethylenamide, polyethylenimines (Lupasol ®, Polymin ®), polyethers, polyurethanes, polyvinyl acetates, Tylose and copolymers of these polymers.
- a suitable gelling agent is, for example, carrageen (Satiagel ®).
- the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
- the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
- UUV ultra-low-volume
- the formulations in question give, after dilution of from two to ten times, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
- formulations are: 1. Products for dilution in water
- a compound I according to the invention 20 parts by weight of a compound I according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone solved. Dilution in water gives a dispersion.
- the active ingredient content is 20% by weight.
- a compound I according to the invention 25 parts by weight of a compound I according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
- This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
- the formulation has an active ingredient content of 25% by weight.
- Parts by weight of dispersing and wetting agents and 70 parts by weight of water or an organic solvent are comminuted in a stirred ball mill to a fine suspension of active ingredient. Dilution in water results in a stable suspension of the active ingredient.
- the active ingredient content in the formulation is 20% by weight.
- 50 parts by weight of a compound I according to the invention are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
- the formulation has an active ingredient content of 50% by weight.
- WP, SP Water-dispersible and Water-Soluble Powders (WP, SP) 75 parts by weight of a compound I according to the invention are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
- the active ingredient content of the formulation is 75% by weight.
- the active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring.
- the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
- Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water.
- the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
- the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
- UUV ultra-low-volume
- wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, optionally also just before use (tank mix) are added. These agents can usually be mixed into the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
- adjuvants in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ® ; Alcohol alkoxylates, eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®; EO-PO block polymers, eg. B. Pluro- nic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
- organically modified polysiloxanes eg Break Thru S 240 ®
- Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
- EO-PO block polymers eg. B. Pluro
- the agents according to the invention may also be present together with other active substances, for example with herbicides, insecticides, growth regulators such as prohexadione-Ca, fungicides or else with fertilizers.
- other active substances for example with herbicides, insecticides, growth regulators such as prohexadione-Ca, fungicides or else with fertilizers.
- Azoxystrobin dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3- methoxy-methyl acrylate;
- Carboxylic acid morpholides Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide (picobenzamide), zoxamide;
- bitertanol bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetracona - zole, triadimenol, triadimefon, triticonazole;
- - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole; Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;
- Nitrogen-containing heterocyclyl compounds - pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine;
- Pyrimidines bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
- Dicarboximides iprodione, procymidone, vinclozolin;
- acibenzolar-S-methyl anilazine, captan, captafol, dazomet, diclomezine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- (4 -methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6-iodo 3-propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide;
- guanidines dodine, iminoctadine, guazatine
- - Antibiotics Kasugamycin, Polyoxins, Streptomycin, Validamycin A
- Organometallic compounds fentin salts
- Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
- Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
- Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, toluylfluanid, flusulfamides, phthalides, hexachlorobenzene, pencycuron, quintozene;
- Nitrophenyl derivatives binapacryl, dinocap, dinobuton;
- Inorganic active substances Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, sulfur; - Other: Spiroxamine, Cyflufenamid, Cymoxanil, Metrafenon. synthesis Examples
- the solid was dissolved in 200 ml of ice-water and the solution was adjusted to pH 2 with 10% strength hydrochloric acid.
- the precipitate was extracted twice with methyl tert-butyl ether and the combined organic phases were washed with saturated aqueous sodium chloride solution. After drying and evaporation of the solvent at reduced pressure, 5.50 g of the above acid were isolated as a white powder of mp 167-169 ° C.
- the active compounds were prepared as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or dimethyl sulfoxide and the emulsifier Uniperol ® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkyl kylphenole) in the volume ratio solvent Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the desired drug concentration. Efficacy against the gray mold on pepper leaves caused by Botrytis cinerea in protective application
- test plants were placed in a climatic chamber with 22 to 24 0 C, darkness and high humidity. After 5 days, the extent of fungal attack on the
- Pots with wheat plants of the "Chancellor" variety were sprayed to drip point with an aqueous suspension having the active ingredient concentration given below. The following day, the pots were inoculated with an aqueous spore suspension of Leposphaeria nodorum (syn.Stagonospora nodorum, Septoria nodorum) - Finally, the plants were placed in a chamber at 20 0 C and maximum humidity.After 8 days, the leaf spot disease on the untreated but infected control plants had developed so strong that the infection could be determined visually in%.
- Paprika seedlings of the cultivar "Neusiedler Ideal Elite" were sprayed to drip point with an aqueous suspension in the concentration of active substance indicated below, after 2-3 leaves had developed well, the next day the treated plants were treated with a spore suspension of Botrytis cinerea, Inoculated with 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution, the test plants were then placed in a climatic chamber at 22-24 ° C, in the dark and high humidity conditions, after 5 days the extent of fungal attack on the leaves visually determined in%.
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- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Pest Control & Pesticides (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catching Or Destruction (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Insulated Conductors (AREA)
Abstract
Description
Claims
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
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KR1020077021082A KR101288635B1 (ko) | 2005-02-16 | 2006-02-15 | 피라졸 카르복시산 아닐리드, 그의 제조 방법 및 그를함유하는 병원성 진균류 방제를 위한 제제 |
EA200701624A EA012667B1 (ru) | 2005-02-16 | 2006-02-15 | Анилиды пиразолкарбоновой кислоты и содержащее их средство для борьбы с патогенными грибами |
EP06708289.1A EP1856055B1 (de) | 2005-02-16 | 2006-02-15 | Pyrazolcarbonsäureanilide, verfahren zu ihrer herstellung und sie enthaltende mittel zur bekämpfung von schadpilzen |
US11/883,957 US8008232B2 (en) | 2005-02-16 | 2006-02-15 | Pyrazolecarboxanilides, process for their preparation and compositions comprising them for controlling harmful fungi |
BRPI0608157-6 BRPI0608157B1 (pt) | 2005-02-16 | 2006-02-15 | compostos, agente para combater fungos nocivos, processo para combater fungos nocivos fitopatogênicos e uso dos compostos |
CA2597022A CA2597022C (en) | 2005-02-16 | 2006-02-15 | Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi |
MX2007008997A MX2007008997A (es) | 2005-02-16 | 2006-02-15 | Anilidas de acido pirazolcarboxilico, un procedimiento para su obtencion y productos que contienen las mismas para combatir hongos nocivos. |
AU2006215642A AU2006215642B2 (en) | 2005-02-16 | 2006-02-15 | Pyrazole carboxylic acid anilides, method for the production thereof and agents containing them for controlling pathogenic fungi |
RS20140674A RS53674B1 (en) | 2005-02-16 | 2006-02-15 | Pyrazolecarboxylic acid anilides, a process for their preparation and compositions for the control of pathogenic fungi containing them |
SI200631851T SI1856055T1 (sl) | 2005-02-16 | 2006-02-15 | Anilidi pirazol karboksilne kisline, postopek za njihovo proizvodnjo in sredstva, ki jih vsebujejo za nadzor patogenih gliv |
PL06708289T PL1856055T3 (pl) | 2005-02-16 | 2006-02-15 | Anilidy kwasu pirazolokarboksylowego, sposób ich wytwarzania i zawierające je środki do zwalczania szkodliwych grzybów |
CN2006800044802A CN101115723B (zh) | 2005-02-16 | 2006-02-15 | 吡唑甲酰苯胺、其制备方法以及用于防治有害真菌的包含它们的试剂 |
DK06708289.1T DK1856055T3 (en) | 2005-02-16 | 2006-02-15 | PYRAZOLCARBOXYLIC ACIDANILIDES, METHOD OF PREPARING THEM AND AGENTS CONTAINING SUCH MATERIALS |
JP2007554584A JP5210638B2 (ja) | 2005-02-16 | 2006-02-15 | ピラゾールカルボキシアニリド、それらの製造方法及び有害菌を防除するためのそれらを含む組成物 |
NZ560208A NZ560208A (en) | 2005-02-16 | 2006-02-15 | Pyrazole carboxylic acid anilides, method for their production therefore and agents containing them for controlling pathogenic fungi |
AP2007004153A AP2868A (en) | 2005-02-16 | 2006-02-15 | Pyrazolecarboxanilides, processes for their preparation and compositions comprising them for controlling harmful fungi |
ES06708289.1T ES2524606T3 (es) | 2005-02-16 | 2006-02-15 | Anilidas de ácido pirazolcarboxílico, procedimientos para su preparación y agentes que contienen las mismas para combatir hongos patógenos |
IL184806A IL184806A (en) | 2005-02-16 | 2007-07-24 | Carboxylic acid anilides anilides, preparations for the control of harmful fungi containing them and their intermediates |
HRP20141195TT HRP20141195T1 (hr) | 2005-02-16 | 2014-12-10 | Anilidi pirazolkarboksilne kiseline, postupak za njihovo dobijanje i kompozicije za kontrolu patogenih gljiva koje ih sadrže |
Applications Claiming Priority (2)
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DE102005007160A DE102005007160A1 (de) | 2005-02-16 | 2005-02-16 | Pyrazolcarbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
DE102005007160.0 | 2005-02-16 |
Publications (1)
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WO2006087343A1 true WO2006087343A1 (de) | 2006-08-24 |
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PCT/EP2006/050962 WO2006087343A1 (de) | 2005-02-16 | 2006-02-15 | Pyrazolcarbonsäureanilide, verfahren zu ihrer herstellung und sie enthaltende mittel zur bekämpfung von schadpilzen |
Country Status (33)
Country | Link |
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US (1) | US8008232B2 (de) |
EP (1) | EP1856055B1 (de) |
JP (2) | JP5210638B2 (de) |
KR (1) | KR101288635B1 (de) |
CN (1) | CN101115723B (de) |
AP (1) | AP2868A (de) |
AR (1) | AR053019A1 (de) |
AU (1) | AU2006215642B2 (de) |
BR (1) | BRPI0608157B1 (de) |
CA (1) | CA2597022C (de) |
CR (1) | CR9335A (de) |
CY (1) | CY1115765T1 (de) |
DE (1) | DE102005007160A1 (de) |
DK (1) | DK1856055T3 (de) |
EA (2) | EA012667B1 (de) |
ES (1) | ES2524606T3 (de) |
HR (1) | HRP20141195T1 (de) |
HU (1) | HUS1500015I1 (de) |
IL (1) | IL184806A (de) |
IN (1) | IN2007KO03068A (de) |
MA (1) | MA29431B1 (de) |
MX (2) | MX2007008997A (de) |
NZ (1) | NZ560208A (de) |
PE (1) | PE20061025A1 (de) |
PL (1) | PL1856055T3 (de) |
PT (1) | PT1856055E (de) |
RS (1) | RS53674B1 (de) |
SI (1) | SI1856055T1 (de) |
TW (1) | TWI365872B (de) |
UA (1) | UA91537C2 (de) |
UY (1) | UY29376A1 (de) |
WO (1) | WO2006087343A1 (de) |
ZA (1) | ZA200707854B (de) |
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