[go: up one dir, main page]

EP2046780A1 - Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant - Google Patents

Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant

Info

Publication number
EP2046780A1
EP2046780A1 EP07787668A EP07787668A EP2046780A1 EP 2046780 A1 EP2046780 A1 EP 2046780A1 EP 07787668 A EP07787668 A EP 07787668A EP 07787668 A EP07787668 A EP 07787668A EP 2046780 A1 EP2046780 A1 EP 2046780A1
Authority
EP
European Patent Office
Prior art keywords
sub
substituted
compounds
formula
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07787668A
Other languages
German (de)
English (en)
Inventor
Jochen Dietz
Thomas Grote
Bernd Müller
Jan Klaas Lohmann
Jens Renner
Sarah Ulmschneider
Alice GLÄTTLI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP07787668A priority Critical patent/EP2046780A1/fr
Publication of EP2046780A1 publication Critical patent/EP2046780A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • Azolylmethyloxirane their use for controlling phytopathogenic fungi and agents containing them
  • the present invention relates to Azolylmethyloxirane of the general formula I.
  • a or B is phenyl which with a CN and optionally substituted by one to three of the following substituents: halogen, NO2, amino, Ci-C 4 -alkyl, -C 4 -alkoxy, Ci-C 4 - haloalkyl, Ci-C4- haloalkoxy, Ci-C 4 alkylamino, Ci-C 4 dialkylamino, thio, or Ci -C 4 -alkyl alkylthio, substituted,
  • a or B is phenyl or 5-membered or 6-membered heteroaryl, where these substituents are optionally substituted by one to three of the following substituents: halogen, CN, NO 2 , amino, C 1 -C 4 -alkyl, C 1 -C 4 - Alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -
  • the invention relates to the use of the compounds of formula I for the control of phytopathogenic fungi and agents containing them.
  • Azolylmethyloxirane their preparation and their use in crop protection are known for example from EP-A 0 094 564 and EP-A 0 196 038.
  • the present invention an object of the invention to provide new Azolylmethyloxirane with an improved fungicidal effect available. This object has been achieved with the compounds of formula I described above.
  • the compound I is able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms contained in them.
  • inorganic acids examples include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
  • Suitable organic acids are, for example, formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms ), Arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl bearing one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or diphosphonic acids (aromatic radicals such as phenyl and Naphthyl which one or two
  • Carry phosphoric acid residues wherein the alkyl or aryl radicals may carry further substituents, e.g. p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
  • the metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, copper, Zinc and others into consideration. Particularly preferred are the metal ions of the elements of the subgroups of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • the corresponding CN-substituted phenyl is prepared from an aryl halide.
  • Chloro, bromine and iodine compounds in question can be carried out thermally with cyanides such as Cu (I) CN, in high boiling solvents such as NMP or DMF or DMSO or nitrobenzene.
  • cyanides such as Cu (I) CN
  • high boiling solvents such as NMP or DMF or DMSO or nitrobenzene.
  • An example of this is, for example, Bioorganic & Medical Cursive Letters, 16 (22), 5763-5766; 2006 or Journal of Medicinal Chemistry, 49 (2), 727-739; Of 2006.
  • the reaction can also be carried out under metal catalysis.
  • Suitable catalysts are various transition metal complexes in question, such as. As nickel or palladium.
  • the cyanide source can i.a. an alkali metal cyanide such as sodium cyanide and potassium cyanide, or a transition metal cyanide such as nickel cyanide or zinc cyanide.
  • An example of a palladium-catalyzed cyanation can be found in Bioorganic & Medicinal Chemistry Letters, 16 (21), 5488-5492; 2006, Chem. Eur. J. 2003, 9, 1828, or in WO2006021886.
  • Halogen fluorine, chlorine, bromine and iodine
  • Haloalkyl Alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above.
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluoro, chloro or bromo.
  • the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred.
  • (C 1 -C 4) -haloalkyl more preferably (C 1 -C 2) -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl; Alkoxy: for an oxygen-
  • Haloalkoxy alkoxy, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine.
  • haloalkoxy radicals are OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2 , 2-Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5 , 2-fluoro
  • Alkylthio Alkyl as defined above attached via an S atom.
  • 5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1, 2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1, 3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, in particular 2 -Furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazoly
  • 6-membered heteroaryl containing one, two, three or four, preferably one, two or three nitrogen atoms, wherein the heteroaryl can be attached via C or N, if present: 6-membered ring heteroaryl groups which contain, in addition to carbon atoms, one to four or may contain one to three nitrogen atoms as ring members, eg Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-tirazinyl, 1, 3,5-triazinyl, in particular 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl , 4-pyridazinyl, 2-
  • the novel compounds of formula I contain chiral centers and are generally obtained in the form of racemates or as mixtures of diastereomers of erythro and threo forms.
  • the erythro and threo diastereomers can be separated in the compounds of the invention, for example, due to their different solubility or by column chromatography and isolated in pure form. From such uniform pairs of diastereomers can be obtained by known methods uniform enantiomers.
  • antimicrobial agents it is possible to use both the uniform diastereomers or enantiomers and also their mixtures obtained in the synthesis. The same applies to the fungicides.
  • the compounds according to the invention can be present in various crystal modifications which may differ in their biological activity. They are also the subject of the present invention.
  • the substituent A or B is phenyl, d- with a CN and possibly additionally from one to three of the following substituents: halogen, NO2, amino, Ci-C 4 -alkyl, -C 4 -alkoxy C 4 haloalkyl, Ci- C 4 haloalkoxy, Ci-C 4 alkylamino, Ci-C 4 -dialkylamino, thio or Ci-C 4 alkylthio, are substituted.
  • the CN substituent is in the 4-position of the phenyl ring.
  • the phenyl ring is substituted in the 2,4 position.
  • a or B is phenyl which, with one CN and one to three further substituents, is selected from one to three of the following substituents: halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 - Haloalkyl or CrC 4 - haloalkoxy substituted.
  • the substituent A or B is phenyl which is substituted with one CN and one to three further substituents selected from halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
  • the substituent A or B is phenyl substituted with one CN and one to three halogens. In another embodiment, the substituent A or B is phenyl which is substituted with a CN and one of the abovementioned substituents.
  • the substituent A or B is phenyl substituted with a CN and another substituent selected from halogen.
  • the substituent A or B is phenyl which is substituted by one CN only.
  • the substituent A or B is phenyl substituted with one CN only for the case of the substituent A in the 4-position and for the case of the substituent B in the 2-position.
  • A is A1.
  • A is A8.
  • A is A9.
  • A is A15.
  • A is A16.
  • A is A17. In another embodiment, A is A18.
  • A is A19.
  • A is A23.
  • B is B1.
  • B is B6.
  • B is B7.
  • B is B8.
  • B stands for B9. In another embodiment, B is B10.
  • B is B15. In a particularly preferred embodiment, B is B16. In another embodiment, B is B17.
  • B stands for B18.
  • B is B19.
  • B is B22.
  • B is B23.
  • the respective other substituent A or B is phenyl substituted by one to three of the following substituents: halogen, CN, NO 2, amino Ci-C4 -alkyl, Ci-C 4 alkoxy, Ci is -C 4 -haloalkyl, Ci-C 4 -
  • Ci-C 4 -alkylamino Ci-C 4 -dialkylamino, thio or Ci-C 4 -alkylthio is substituted.
  • the respective other substituent A or B is phenyl substituted by one to three of the following substituents: halogen, Ci-C4-alkyl, d- C4-alkoxy, Ci-C4-haloalkyl or Ci-C 4 is Haloalkoxy is substituted.
  • the other substituent A or B is phenyl which is substituted by one to three halogen.
  • the substituent A or B is a 5-membered heteroaryl which is optionally substituted by one to three of the following substituents: halogen, CN, NO 2 , amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, 4 -haloalkoxy, CrC 4 Ci-C4-haloalkyl, Ci-C - alkylamino, Ci-C 4 dialkylamino substituted, thio, or Ci-C 4 alkylthio.
  • the substituent A or B is a 5-membered heteroaryl selected from furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, 1, 3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadia - zolyl.
  • the substituent A or B is a 5-membered heteroaryl selected from furyl, thienyl, pyrrolyl, pyrazolyl, triazolyl and thiazolyl.
  • the substituent A or B is a 5-membered heteroaryl selected from thienyl, triazolyl and pyrazolyl.
  • the substituent A or B is a 5-membered heteroaryl which is substituted by one to three of the following substituents: halogen, CN, NO 2, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C i -C 4 haloalkyl, Ci-C4-haloalkoxy, -C 4 - substituted 4 dialkylamino, thio, or Ci-C 4 alkylthio, alkylamino, Ci-C.
  • the substituent A or B is a 5-membered heteroaryl which is substituted by one to three of the following substituents: halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkyl. Haloalkoxy is substituted.
  • the substituent A or B is a 5-membered heteroaryl which is substituted by one to three of the following substituents halogen, Ci-C4-alkyl or Ci-C4-alkoxy.
  • the substituent A or B is a 6-membered heteroaryl which is optionally substituted by one to three of the following substituents: halogen, CN, NO 2, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -Haloalkyl, Ci-C4-haloalkoxy, C1-C4-alkylamino, Ci-C4-dialkylamino, thio or Ci-C4-alkylthio, is substituted.
  • the substituent A or B is a 6-membered heteroaryl selected from pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl and 1, 3,5-triazinyl ,
  • the substituent A or B is a 6-membered heteroaryl selected from pyridyl and pyrimidinyl.
  • the substituent A or B is a 6-membered heteroaryl which is substituted by one to three of the following substituents: halogen, CN, NO 2, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -Haloalkyl, Ci-C4-haloalkoxy, C1-C4-alkylamino, Ci-C4-dialkylamino, thio or Ci-C4-alkylthio, is substituted.
  • the substituent A or B is a 6-membered heteroaryl which is substituted by one to three of the following substituents: halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy is substituted.
  • the substituent A or B is a 6-membered heteroaryl which is substituted by one to three of the following substituents: halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
  • the compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes, in particular from the class of the Oomycetes. They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. They are particularly important for the control of a variety of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soy, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers. Beans, tomatoes, potatoes and pumpkins, as well as the seeds of these plants.
  • Cochliobolus species on corn, cereals, rice e.g. Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice,
  • Drechslera species Pyrenophora species on maize, cereals, rice and turf, e.g. D.teres to barley or D. tritici-repentis to wheat,
  • Gibberella species on cereals and rice e.g., Gibberella fujikuroi on rice
  • Mycosphaerella species on cereals, bananas and peanuts e.g. M. graminicola on wheat or M.fijiensis on bananas,
  • Peronospora species on cabbage and bulbous plants such as P. brassicae on cabbage or P. destructor on onion, • Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans,
  • Pseudocercosporella herpotrichoides on cereals Pseudoperonospora on various plants, e.g. P. cubensis on cucumber or P. humili on hops,
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals, or P. asparagi on asparagus,
  • Venturia species scab
  • apples and pears like. e.g. V. inaequalis to apple.
  • Peronosporomycetes such as Peronospora species, Phytophthora species, Plasmopara viticola, Pseudoperonospora species and Pythium species.
  • 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.
  • 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.
  • active ingredient in general, amounts of active ingredient of 1 to 1000 g / 100 kg, preferably 5 to 100 g / 100 kg of seed are needed.
  • 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 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.
  • 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:
  • Ketones e.g., cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids, and fatty acid esters.
  • solvent mixtures can also be used
  • Carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates);
  • ground natural minerals e.g., kaolins, clays, talc, chalk
  • ground synthetic minerals e.g., 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.
  • nonionic and anionic emulsifiers eg polyoxyethylene Fatty alcohol ethers, alkylsulfonates and arylsulfonates
  • 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 flour, 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
  • 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). Examples of formulations are: 1. Products for dilution in water
  • a Water-soluble concentrates (SL, LS)
  • DC Dispersible Concentrates
  • Emulsifiable Concentrates 15 parts by weight of the active compounds are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has 15% by weight active ingredient content.
  • the active compounds 25 parts by weight of the active compounds 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.
  • the active ingredients 20 parts by weight of the active ingredients are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of the active compounds are finely ground with the addition of 50 parts by weight of dispersing 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.
  • the active ingredients 75 parts by weight of the active ingredients are added with the addition of 25 parts by weight of dispersing and Wetting agents and silica gel in a rotor-Strator mill. 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.
  • 0.5 parts by weight of the active ingredients are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • LS water-soluble concentrates
  • FS suspensions
  • DS dusts
  • WS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gel formulations GF
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or Pouring be applied.
  • the forms of application depend entirely on the purposes of 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 (wettable powders, oil dispersions) by adding water.
  • the substances for the preparation of emulsions, pastes or oil dispersions, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. 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 To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • 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 ®
  • sodium dioctylsulfosuccinate e. B. Leophen RA ®.
  • the agents according to the invention in the form of application as fungicides, may also be present together with other active substances, e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • other active substances e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
  • fungicides for example, in many cases the spectrum of action can be broadened or resistance developments can be prevented. In many cases, synergistic effects are obtained.
  • a further subject matter of the present invention is a combination of at least one azolylmethyloxirane of the formula I, in particular an azolylmethyloxirane disclosed as preferred in the present description and / or an agriculturally acceptable salt thereof and at least one further fungicidal, insecticidal, herbicidal and / or growth-regulating active ingredient, wherein a synergistic effect may occur.
  • Another object of the present invention is a pesticidal composition
  • a pesticidal composition comprising at least one compound of the formula I, in particular a compound of the formula I described as being preferred in the present specification and / or an agriculturally acceptable acid addition or metal salt thereof and at least one solid or liquid carrier ,
  • Such a pesticidal composition may contain at least one other fungicidal, insecticidal and / or herbicidal active ingredient, whereby a synergistic effect may also occur.
  • Azoxystrobin Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methyminostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, 3-methoxy- 2- (2- (N- (4-methoxyphenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester;
  • Carboxylic acid morpholides Dimethomorph, Flumorph; Benzoic acid amides: flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide;
  • carboxamides carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;
  • Triazoles azaconazole, bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothiocona - zole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chloro-phenyl) -2 - ([1, 2,4] triazol-1-yl) -cycloheptanol;
  • - imidazoles cyazofamide, imazalil, imazalil sulfate, 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, 2,3,5,6-tetrachloro-4-methanesulfonyl -pyridine, 3,4,5-trichloro-pyridine-2,6-dicarbonitrile, N- (1 - ( ⁇ -bromo-S-chloro-pyridine-y-O-ethoxy) -dichloro-nicotinamide, N- ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2,4-dichloro-nicotinamide;
  • - pyrimidines bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, panipyrim, nitrapyrin, nuarimol, pyrimethanil;
  • Dicarboximides fluoroimide, iprodione, procymidone, vinclozolin; - Other: Acibenzolar-S-methyl, Amisulbrom, Anilazine, Blasticidin-S, Captafol, Captan, Chinomethionat, Dazomet, Debacarb, Diclomethine, Difenzoquat, Difenzoquat-methylsulphate, Famoxadone, Fenamidone, Fenoxanil, Fenpropidin, Folpet, Octhilinone, Oxolinic acid, Piperalin , Sample azoles, proquinazide, pyroquilon, quinoxyfen, triazoxide, tricyclazole, triforine, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1,5-a] pyimidine, 2-but
  • Thio and dithiocarbamates Ferbam, Mancozeb, Maneb, Metam, Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram; Carbamates: Diethofencarb, Benthiavalicarb, Iprovalicarb, Propamocarb,
  • Guanidines dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilat); - antibiotics: kasugamycin, kasugamycin hydrochloride hydrate, polyoxins, streptomycin, validamycin A;
  • Fentin salts such as, for example, fentin acetate, fentin chloride, fentin hydroxide;
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl;
  • Organochlorine compounds chlorothalonil, dichlofluanid, dichlorophen, flusulfamides, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phthalocyanine
  • Inorganic active substances Phosphorous acid and its salts, sulfur, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate;
  • the present invention further relates to the compositions listed in Table B, wherein in each case one row of Table B corresponds to a fungicidal composition comprising a compound of the formula I (component 1), which is preferably one of the compounds described herein as preferred, and the each additional active ingredient (component 2) indicated in the respective line.
  • component 1 in each row of table B is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 68.
  • the active compounds II mentioned above as component 2 their preparation and their action against harmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html); they are commercially available.
  • the compounds named after IUPAC, their preparation and their fungicidal action are also known [cf. EP-A 226 917; EP-A 10 28 125; EP-A 10 35 122; EP-A 12 01 648; WO 98/46608; WO 99/24413; WO 03/14103; WO 03/053145; WO 03/066609; WO 04/049804].
  • the active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or DMSO and the emulsifier Wettol EM 31 (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) 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 drug concentration given below.
  • Wettol EM 31 wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the plants treated with the active compounds 69.1 and 69.3 with 63 ppm aqueous aqueous preparation showed an infection of 0%, while the untreated plants were 90% infected.
  • the plants treated with the active ingredient 69.3 with 63 ppm aqueous aqueous preparation showed an attack of 1%, while the untreated plants were 90% infected.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

L'invention concerne des azolylméthyloxiranes représentés par la formule générale (I) dans laquelle A ou B est phényle substitué avec un CN et éventuellement par un à trois des substituants suivants, halogène, NO<SUB>2</SUB>, amino, C<SUB>1</SUB>-C<SUB>4</SUB>-alkyle, C<SUB>1</SUB>-C<SUB>4</SUB>-alkoxy, C<SUB>1</SUB>-C<SUB>4</SUB>- halogénoalkyle, C<SUB>1</SUB>-C<SUB>4</SUB>-halogénoalkoxy, C<SUB>1</SUB>-C<SUB>4</SUB>-alkylamino, C<SUB>1</SUB>-C<SUB>4</SUB>-dialkylamino, thio ou C<SUB>1</SUB>-C<SUB>4</SUB>-alkylthio, et l'autre substituant, respectivement A ou B, est phényle ou hétéroaryle à 5 ou 6 éléments, ces substituants étant éventuellement substitués par un à trois des substituants suivants, halogène, CN, NO<SUB>2</SUB>, amino, C<SUB>1</SUB>-C<SUB>4</SUB>-alkyle, C<SUB>1</SUB>-C<SUB>4</SUB>-alkoxy, C<SUB>1</SUB>-C<SUB>4</SUB>- halogénoalkyle, C<SUB>1</SUB>-C<SUB>4</SUB>-halogénoalkoxy, C<SUB>1</SUB>-C<SUB>4</SUB>-alkylamino, C<SUB>1</SUB>-C<SUB>4</SUB>-dialkylamino, thio ou C<SUB>1</SUB>-C<SUB>4</SUB>-alkylthio. L'invention concerne également les sels d'addition acides ou les sels de métaux desdits composés, tolérés par les plantes, l'utilisation des composés représentés par la formule (I) dans la lutte contre des champignons phytopathogènes et des agents contenant ces composés.
EP07787668A 2006-07-24 2007-07-18 Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant Withdrawn EP2046780A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07787668A EP2046780A1 (fr) 2006-07-24 2007-07-18 Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06117716 2006-07-24
EP07787668A EP2046780A1 (fr) 2006-07-24 2007-07-18 Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant
PCT/EP2007/057404 WO2008012246A1 (fr) 2006-07-24 2007-07-18 Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant

Publications (1)

Publication Number Publication Date
EP2046780A1 true EP2046780A1 (fr) 2009-04-15

Family

ID=38719485

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07787668A Withdrawn EP2046780A1 (fr) 2006-07-24 2007-07-18 Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant

Country Status (11)

Country Link
US (1) US8236788B2 (fr)
EP (1) EP2046780A1 (fr)
JP (1) JP5148610B2 (fr)
CN (1) CN101495473A (fr)
AR (1) AR062027A1 (fr)
BR (1) BRPI0714365A2 (fr)
CL (1) CL2007002151A1 (fr)
PE (1) PE20080949A1 (fr)
TW (1) TW200817381A (fr)
UY (1) UY30502A1 (fr)
WO (1) WO2008012246A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2007263091B2 (en) * 2006-06-21 2012-03-08 Basf Se Azolylmethyloxiranes, their use for controlling phytopathogenic fungi and compositions comprising them
BRPI0713131A2 (pt) * 2006-06-23 2012-04-17 Basf Se compostos, uso de compostos, composição para a proteção de colheitas, semente, e, processo para combater fungos fitopatogênicos
CN101484450B (zh) * 2006-07-05 2011-08-03 巴斯夫欧洲公司 唑基甲基环氧乙烷及其在防治植物病原性真菌中的用途和包含所述化合物的试剂
BRPI0713450A2 (pt) * 2006-07-05 2012-01-31 Basf Se compostos, uso de compostos, composição de proteção de colheita, semente, e, processo para combater fungos fitopatogênicos
JP2009544650A (ja) * 2006-07-25 2009-12-17 ビーエーエスエフ ソシエタス・ヨーロピア アゾリルメチルオキシラン、植物病原菌類を防除するためのその使用、およびそれを含む薬剤
WO2008077724A1 (fr) * 2006-12-22 2008-07-03 Basf Se Azolylméthyloxiranes, leur utilisation pour lutter contre les champignons phytopathogènes et agents les contenant
US20110294855A1 (en) 2009-01-30 2011-12-01 Bayer Cropscience Ag Active Compound Combinations
CA2750963A1 (fr) 2009-01-30 2010-08-05 Bayer Cropscience Ag Combinaisons de composes actifs
EP3727362A4 (fr) 2017-12-19 2021-10-06 PureTech LYT, Inc. Promédicaments lipidiques d'acide mycophénolique et leurs utilisations

Family Cites Families (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4061656A (en) 1975-11-14 1977-12-06 Hoffmann-La Roche Inc. Polyene compounds
GB1560699A (en) 1975-11-14 1980-02-06 Hoffmann La Roche 2-or 3-thienyl-polyenes
US4116975A (en) 1976-10-18 1978-09-26 Hoffmann-La Roche Inc. Polyene compounds
IL68433A (en) 1982-05-14 1986-04-29 Basf Ag Azolylmethyloxiranes,their manufacture and their use as fungicides and in pharmaceutical compositions
DE3218129A1 (de) * 1982-05-14 1983-11-17 Basf Ag, 6700 Ludwigshafen Azolylmethyloxirane, ihre herstellung und verwendung als arzneimittel
DE3218130A1 (de) * 1982-05-14 1983-11-17 Basf Ag, 6700 Ludwigshafen Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide
JPS6070682A (ja) 1983-08-18 1985-04-22 バロ−ス・コ−ポレ−シヨン 電気コネクタ装置
IE58738B1 (en) * 1984-09-05 1993-11-03 Ici Plc Antifungal azole compounds
CA1271764A (fr) 1985-03-29 1990-07-17 Stefan Karbach Azolylmethyloxiranes; leur preparation et leur utilisation pour la protection de cultures
DE3511411A1 (de) * 1985-03-29 1986-10-02 Basf Ag, 6700 Ludwigshafen Verwendung von azolylmethyloxiranen zur bekaempfung von viralen erkrankungen
DE3545319A1 (de) 1985-12-20 1987-06-25 Basf Ag Acrylsaeureester und fungizide, die diese verbindungen enthalten
DE3601927A1 (de) 1986-01-23 1987-07-30 Basf Ag Alpha, beta-substituierte acroleine, verfahren zu deren herstellung und deren verwendung
DE3702029A1 (de) * 1987-01-24 1988-08-04 Basf Ag Waessriges oder pulverfoermiges, wasserdispergierbares praeparat eines in wasser schwerloeslichen pharmazeutischen wirkstoffs und verfahren zu seiner herstellung
DE3737888A1 (de) * 1987-11-07 1989-05-18 Basf Ag Verfahren zur beeinflussung des pflanzenwachstums durch azolylmethyloxirane
DE3907729A1 (de) * 1989-03-10 1990-09-13 Basf Ag Trifluormethylphenylazolylmethyloxirane, verfahren zu ihrer herstellung und deren verwendung als pflanzenschutzmittel
HU204665B (en) * 1989-03-21 1992-02-28 Basf Ag Herbicidal and growth regulating compositions comprising azolylmethyl oxirane derivative and process for utilizing them
IL95493A0 (en) * 1989-09-09 1991-06-30 Basf Ag Azolylmethyloxiranes,their manufacture and their use as fungicides
DE3942333A1 (de) 1989-12-21 1991-06-27 Basf Ag Fungizide azolylmethyloxirane
DE4028392A1 (de) 1990-09-07 1992-03-12 Basf Ag Azolylmethyloxirane und diese enthaltende fungizide
US5210208A (en) 1990-09-24 1993-05-11 Rhone-Poulenc Rorer Pharmaceuticals Inc. Disubstituted aryl compounds exhibiting selective leukotriene b4 antagonist activity
JPH08217777A (ja) * 1995-02-10 1996-08-27 Nippon Nohyaku Co Ltd ２−ピラゾリン−５−オン誘導体及びその中間体並びに除草剤
TW460476B (en) 1997-04-14 2001-10-21 American Cyanamid Co Fungicidal trifluoromethylalkylamino-triazolopyrimidines
DE19750012A1 (de) 1997-11-12 1999-05-20 Bayer Ag Isothiazolcarbonsäureamide
IT1296924B1 (it) 1997-12-05 1999-08-03 Zambon Spa Composti diolici intermedi per la preparazione di composti ad attivita' antimicotica
IT1303800B1 (it) 1998-11-30 2001-02-23 Isagro Ricerca Srl Composti dipeptidici aventi elevata attivita' fungicida e loroutilizzo agronomico.
AU770077B2 (en) 1999-03-11 2004-02-12 Dow Agrosciences Llc Heterocyclic substituted isoxazolidines and their use as fungicides
UA73307C2 (uk) 1999-08-05 2005-07-15 Куміаі Кемікал Індастрі Ко., Лтд. Похідна карбамату і фунгіцид сільськогосподарського/садівницького призначення
US6442228B1 (en) * 2000-04-20 2002-08-27 Ge Medical Systems Global Technology Company, Llc Data acquisition modifications for improved reconstruction with conventional CT
FR2828196A1 (fr) 2001-08-03 2003-02-07 Aventis Cropscience Sa Derives de chromone a action fongicide, procede de preparation et application dans le domaine de l'agriculture
AU2002354251A1 (en) 2001-12-21 2003-07-09 Nissan Chemical Industries, Ltd. Bactericidal composition
DE10204390A1 (de) 2002-02-04 2003-08-14 Bayer Cropscience Ag Disubstituierte Thiazolylcarboxanilide
GB0227966D0 (en) 2002-11-29 2003-01-08 Syngenta Participations Ag Organic Compounds
MX2007001986A (es) 2004-08-26 2007-05-10 Pfizer Compuestos de aminoheteroarilo como inhibidores de proteina quinasa.
AU2007263091B2 (en) * 2006-06-21 2012-03-08 Basf Se Azolylmethyloxiranes, their use for controlling phytopathogenic fungi and compositions comprising them
BRPI0713131A2 (pt) * 2006-06-23 2012-04-17 Basf Se compostos, uso de compostos, composição para a proteção de colheitas, semente, e, processo para combater fungos fitopatogênicos
JP2009541263A (ja) * 2006-06-23 2009-11-26 ビーエーエスエフ ソシエタス・ヨーロピア アゾリルメチルオキシラン、植物病原菌類を防除するためのその使用、およびそれを含む組成物
CN101484450B (zh) 2006-07-05 2011-08-03 巴斯夫欧洲公司 唑基甲基环氧乙烷及其在防治植物病原性真菌中的用途和包含所述化合物的试剂
BRPI0713450A2 (pt) 2006-07-05 2012-01-31 Basf Se compostos, uso de compostos, composição de proteção de colheita, semente, e, processo para combater fungos fitopatogênicos
WO2008077724A1 (fr) * 2006-12-22 2008-07-03 Basf Se Azolylméthyloxiranes, leur utilisation pour lutter contre les champignons phytopathogènes et agents les contenant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008012246A1 *

Also Published As

Publication number Publication date
JP5148610B2 (ja) 2013-02-20
US20090270256A1 (en) 2009-10-29
AR062027A1 (es) 2008-08-10
BRPI0714365A2 (pt) 2013-04-02
CN101495473A (zh) 2009-07-29
PE20080949A1 (es) 2008-09-20
TW200817381A (en) 2008-04-16
US8236788B2 (en) 2012-08-07
UY30502A1 (es) 2007-08-31
CL2007002151A1 (es) 2008-01-18
JP2009544655A (ja) 2009-12-17
WO2008012246A1 (fr) 2008-01-31

Similar Documents

Publication Publication Date Title
EP2035414B1 (fr) Azolylméthyloxirane, son utilisation pour lutter contre les champignons pathogènes des plantes et agents contenant ce composé
EP2041122B1 (fr) Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant
EP2038276B1 (fr) Azolylméthyloxiranes, leur utilisation pour lutter contre les champignons pathogènes des plantes et agents contenant ces composés
EP2035415B1 (fr) Azolylméthyloxirane, son utilisation pour lutter contre les champignons pathogènes des plantes et agents contenant ce composé
EP1856055B1 (fr) Anilides d&#39;acide carboxylique pyrazole, procédés de production associés et agents les contenant pour la lutte antifongique
EP2041125B1 (fr) Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant
EP2096921A1 (fr) Azolylmethyloxiranes, leur utilisation pour lutter contre les champignons phytopathogenes et agents les contenant
EP2046780A1 (fr) Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant
WO2008053044A2 (fr) Composés de n-(biphène-2-yl)amide d&#39;acide hétarylcarboxylique
WO2008132021A2 (fr) Mélanges fongicides
EP2046784A2 (fr) Azolylméthyloxiranes, leur utilisation dans la lutte contre des champignons phytopathogènes et agents les contenant
WO2008046856A2 (fr) Compositions fongicides
EP2010514A1 (fr) 3-(pyridine-2-yl)-[1,2,4]-triazines utilisées comme fongicides

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20090224

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA HR MK RS

17Q First examination report despatched

Effective date: 20111230

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20130430