WO2008012246A1 - Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel - Google Patents
Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel Download PDFInfo
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- WO2008012246A1 WO2008012246A1 PCT/EP2007/057404 EP2007057404W WO2008012246A1 WO 2008012246 A1 WO2008012246 A1 WO 2008012246A1 EP 2007057404 W EP2007057404 W EP 2007057404W WO 2008012246 A1 WO2008012246 A1 WO 2008012246A1
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- 0 Cc(c(*)c1)ccc1C#N Chemical compound Cc(c(*)c1)ccc1C#N 0.000 description 2
- OWISXYQFTOYGRO-UHFFFAOYSA-N Cc(c(C)c1)ccc1C#N Chemical compound Cc(c(C)c1)ccc1C#N OWISXYQFTOYGRO-UHFFFAOYSA-N 0.000 description 1
- QLZDTHTXOUOSCV-UHFFFAOYSA-N Cc(cc1)cc(C)c1C#N Chemical compound Cc(cc1)cc(C)c1C#N QLZDTHTXOUOSCV-UHFFFAOYSA-N 0.000 description 1
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- 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.
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- 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
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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EP07787668A EP2046780A1 (de) | 2006-07-24 | 2007-07-18 | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
US12/374,710 US8236788B2 (en) | 2006-07-24 | 2007-07-18 | Azolylmethyloxiranes, use thereof for controlling plant pathogenic fungi, and agents containing the same |
BRPI0714365-6A BRPI0714365A2 (pt) | 2006-07-24 | 2007-07-18 | compostos, uso de compostos, composiÇço para a proteÇço da colheita, semente, e, processo para combater fungos fitopatogÊnicos |
JP2009521224A JP5148610B2 (ja) | 2006-07-24 | 2007-07-18 | 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 |
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EP06117716 | 2006-07-24 | ||
EP06117716.8 | 2006-07-24 |
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WO2008012246A1 true WO2008012246A1 (de) | 2008-01-31 |
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PCT/EP2007/057404 WO2008012246A1 (de) | 2006-07-24 | 2007-07-18 | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
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US (1) | US8236788B2 (de) |
EP (1) | EP2046780A1 (de) |
JP (1) | JP5148610B2 (de) |
CN (1) | CN101495473A (de) |
AR (1) | AR062027A1 (de) |
BR (1) | BRPI0714365A2 (de) |
CL (1) | CL2007002151A1 (de) |
PE (1) | PE20080949A1 (de) |
TW (1) | TW200817381A (de) |
UY (1) | UY30502A1 (de) |
WO (1) | WO2008012246A1 (de) |
Cited By (3)
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WO2010086109A1 (en) | 2009-01-30 | 2010-08-05 | Bayer Cropscience Ag | Active compound combinations |
WO2010086120A1 (en) | 2009-01-30 | 2010-08-05 | Bayer Cropscience Ag | Active compound combinations |
US7910614B2 (en) | 2006-07-25 | 2011-03-22 | Basf Se | Azolylmethyloxiranes, use thereof for controlling plant pathogenic fungi, and agents containing the same |
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WO2007147778A1 (de) * | 2006-06-21 | 2007-12-27 | Basf Se | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
ATE452131T1 (de) * | 2006-06-23 | 2010-01-15 | Basf Se | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
CN101484446B (zh) * | 2006-07-05 | 2011-07-13 | 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 |
EP2041125B1 (de) * | 2006-07-05 | 2011-01-26 | Basf Se | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
JP2010513367A (ja) * | 2006-12-22 | 2010-04-30 | 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、植物病原性菌類を防除するための前記化合物の使用、及び前記化合物を含む組成物 |
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- 2007-07-18 CN CNA2007800282383A patent/CN101495473A/zh active Pending
- 2007-07-18 EP EP07787668A patent/EP2046780A1/de not_active Withdrawn
- 2007-07-18 US US12/374,710 patent/US8236788B2/en not_active Expired - Fee Related
- 2007-07-18 BR BRPI0714365-6A patent/BRPI0714365A2/pt not_active IP Right Cessation
- 2007-07-18 WO PCT/EP2007/057404 patent/WO2008012246A1/de active Application Filing
- 2007-07-18 JP JP2009521224A patent/JP5148610B2/ja not_active Expired - Fee Related
- 2007-07-23 CL CL2007002151A patent/CL2007002151A1/es unknown
- 2007-07-23 TW TW096126794A patent/TW200817381A/zh unknown
- 2007-07-23 AR ARP070103264A patent/AR062027A1/es unknown
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- 2007-07-24 UY UY30502A patent/UY30502A1/es unknown
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---|---|---|---|---|
US7910614B2 (en) | 2006-07-25 | 2011-03-22 | Basf Se | Azolylmethyloxiranes, use thereof for controlling plant pathogenic fungi, and agents containing the same |
WO2010086109A1 (en) | 2009-01-30 | 2010-08-05 | Bayer Cropscience Ag | Active compound combinations |
WO2010086120A1 (en) | 2009-01-30 | 2010-08-05 | Bayer Cropscience Ag | Active compound combinations |
Also Published As
Publication number | Publication date |
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BRPI0714365A2 (pt) | 2013-04-02 |
PE20080949A1 (es) | 2008-09-20 |
AR062027A1 (es) | 2008-08-10 |
JP2009544655A (ja) | 2009-12-17 |
TW200817381A (en) | 2008-04-16 |
JP5148610B2 (ja) | 2013-02-20 |
EP2046780A1 (de) | 2009-04-15 |
UY30502A1 (es) | 2007-08-31 |
CL2007002151A1 (es) | 2008-01-18 |
CN101495473A (zh) | 2009-07-29 |
US8236788B2 (en) | 2012-08-07 |
US20090270256A1 (en) | 2009-10-29 |
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