EP1893021A2 - Utilisation de triazolopyrimidines pour reguler les phytopathologies chez les legumineuses - Google Patents

Utilisation de triazolopyrimidines pour reguler les phytopathologies chez les legumineuses

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Publication number
EP1893021A2
EP1893021A2 EP06753926A EP06753926A EP1893021A2 EP 1893021 A2 EP1893021 A2 EP 1893021A2 EP 06753926 A EP06753926 A EP 06753926A EP 06753926 A EP06753926 A EP 06753926A EP 1893021 A2 EP1893021 A2 EP 1893021A2
Authority
EP
European Patent Office
Prior art keywords
methyl
hydrogen
chloro
legumes
species
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Withdrawn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
EP06753926A
Other languages
German (de)
English (en)
Inventor
Olaf Gebauer
Hans-Ludwig Elbe
Jörg Nico GREUL
Oliver Guth
Herbert Gayer
Ulrich Heinemann
Stefan Herrmann
Peter Dahmen
Ulrike Wachendorff- Neumann
Ingo Wetcholowsky
Hiroyuki Hadano
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1893021A2 publication Critical patent/EP1893021A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to the use of triazolopyrimidines for the control of phytopathogenic fungi, in particular rust species on legumes (legumes).
  • triazolopyrimidines of the formula (I) have very good fungicidal properties against diseases of the soybean, in particular against rust diseases on soy, such as Phakopsora pachyrhizi and Phakopsora meibomiae.
  • the invention relates to the use of triazolopyrimidines of the formula (I) for combating diseases of legumes, in particular of rust diseases in soya.
  • the compounds of group (1) are generally defined by the formula (I).
  • R 1 is Ci-C ⁇ alkyl, Ci-C 6 haloalkyl, or C 2 -C 6 alkenyl
  • R 2 is hydrogen or C] -C 6 alkyl, or
  • R- and R 2 together with the nitrogen atom to which they are attached, form a five or six-membered heterocycle which additionally has up to three heteroatoms selected from May contain nitrogen, oxygen or sulfur and may be substituted with up to 3 groups selected from trifluoromethyl and methyl, where two oxygen atoms may not be adjacent,
  • R 3 is C r C 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkyl, cyano, bromine or chlorine,
  • R 4 to R 8 independently of one another represent hydrogen, fluorine, chlorine, methyl or trifluoromethyl.
  • R 1 is C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl
  • R 2 is hydrogen or C 1 -C 6 alkyl
  • R 1 and R 2 together with the nitrogen atom to which they are attached form a five- or six-membered heterocycme which may additionally contain up to three heteroatoms selected from nitrogen, oxygen or sulfur and up to 3 groups selected from trifluoromethyl and methyl may be substituted, wherein two oxygen atoms may not be adjacent,
  • R 3 is methyl, cyano or chlorine
  • R 4 to R 8 independently of one another represent hydrogen, fluorine, chlorine, methyl or trifluoromethyl.
  • R 1 is 3-methyl-but-2-yl, 3,3-dimethyl-2-yl, 2,2,2-trifluoroethyl or 1,1,1-trifluoro-2-propyl,
  • R 2 is hydrogen, or
  • R 1 and R 2 together represent - (CH 2 ) -CH (CH 3 ) - (CH 2 ) 2 -,
  • R 3 is methyl or chlorine
  • R 4 is methyl, chlorine or fluorine
  • R 5 to R 8 are hydrogen
  • R 1 for 3-methyl-but-2-yl, 3,3 5 -dimethyl-but-2-yl, 2,2,2-trifluoroethyl or 1,1,1-trifluoro-prop-2-yl stands, R 2 is hydrogen, or
  • R 1 and R 2 together represent - (CH 2 ) -CH (CH 3 ) - (CH 2 ) 2,
  • R 3 is methyl or chloro
  • R 4 and R 6 independently of one another are methyl, chlorine or fluorine and R 5 , R 7 and R 8 are hydrogen,
  • R 1 is 3-methyl-but-2-yl, 3,3-dimethyl-2-yl, 2,2,2-trifluoroethyl or 1,1,1-trifluoro-2-propyl,
  • R 2 is hydrogen, or
  • R 1 and R 2 together represent - (CH 2 ) -CH (CH 3 ) - (CH 2 ) 2-
  • R 3 is methyl or chloro
  • R 4 and R 8 independently of one another are methyl, chlorine or fluorine and R 5 , R 6 and R 7 are hydrogen,
  • R 1 is 3-methyl-but-2-yl, 3,3-dimethyl-2-yl, 2,2,2-trifluoroethyl or 1,1,1-trifluoro-2-propyl,
  • R 2 is hydrogen, or
  • R 1 and R 2 together represent - (CH 2 ) -CH (CH 3 ) - (CH 2 ) 2-,
  • R 3 is methyl, or chloro
  • R 4 , R 6 and R 8 independently of one another are methyl, chlorine or fluorine and R 5 and R 7 are hydrogen.
  • R 1 is 3-methyl-2-yl, 3,3-dimethyl-2-yl, 2,2,2-trifluoroethyl or 1,1,1-trifluoro-2-propyl,
  • R 2 is hydrogen, or R 1 and R 2 together represent - (CH 2 ) -CH (CH 3 ) - (CH 2 ) 2,
  • R 3 is chlorine
  • R 4 , R 6 and R 8 are fluorine
  • R 5 and R 7 are hydrogen.
  • the formula (I) particularly includes the following preferred triazolopyrimidines:
  • the compounds of the formula (I) can be used both in pure form and as mixtures of various possible isomeric forms, in particular stereoisomers, such as E and Z, threo and erythro, and optical isomers, such as R and S isomers or Atropisomeren, if appropriate, but also from tautomers vorhegen.
  • the invention includes both the pure isomers and their mixtures.
  • the active compounds according to the invention have very good fungicidal properties and, in addition to the control of rust diseases, can also be used for controlling other phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
  • pathogens of fungal and bacterial diseases which fall under the above-enumerated generic terms, are named: Diseases caused by powdery mildew pathogens such as Blumeria species such as Blumeria graminis; Podosphaera species, such as Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator;
  • Gymnosporangium species such as, for example, Gymnosporangium sabinae
  • Hemileia species such as, for example, Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia species such as Puccinia recondita
  • Uromyces species such as Uromyces appendiculatus
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae;
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
  • Pythium species such as Pythium ultimum
  • Alternaria species such as Alternaria solani
  • Cercospora species such as Cercospora beticola
  • Cladiosporum species such as Cladiosporium cucumerinum
  • Cochliobolus species such as Cochliobolus sativus
  • Colletotrichum species such as Colletotrichum lindemuthanium
  • Cycloconium species such as cycloconium oleaginum
  • Diaporthe species such as Diaporthe citri;
  • Elsinoe species such as Elsinoe fawcettü
  • Gloeosporium species such as, for example, Gloeosporium laeticolor; jjlomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli;
  • Leptosphaeria species such as Leptosphaeria maculans
  • Magnaporthe species such as Magnaporthe grisea
  • Mycosphaerella species such as Mycosphaerella graminicola
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporiurn species such as Rhynchosporium secalis
  • Septoria species such as Septoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Venturia inaequalis
  • Corticium species such as Corticium graminearum
  • Fusarium species such as Fusarium oxysporum
  • Gaeumannomyces species such as Gaeumannomyces graminis
  • Rhizoctonia species such as Rhizoctonia solani
  • Tapesia species such as Tapesia acuformis
  • Thielaviopsis species such as Thielaviopsis basicola
  • Ear and panicle diseases caused by e.g.
  • Alternaria species such as Alternaria spp .
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium spp .
  • Claviceps species such as Claviceps purpurea
  • Fusarium species such as Fusarium culmorum
  • Gibberella species such as Gibberella zeae
  • Monographella species such as Monographella nivalis
  • Sphacelotheca species such as Sphacelotheca reiliana
  • Tilletia species such as Tületia caries
  • Urocystis species such as Urocystis occulta
  • Ustilago species such as Ustilago nuda
  • Penicillium species such as Penicillium expansum; Scler ⁇ tinia species, such as Sclerotinia sclerotiorum; Verticilium species such as, for example, Verticilium alboatrnm;
  • Fusarium species such as Fusarium culmorurn; Phytophthora species, such as Phytophthora cactorum; Pythium species such as Pythium ultimum; Rhizoctonia species, such as Rhizoctonia solani; Sclerotium species, such as Sclerotium rolfsii;
  • Nectria species such as Nectria galligena
  • Monilinia species such as Monilinia laxa
  • Botrytis species such as Botrytis cinerea
  • Rhizoctonia species such as Rhizoctonia solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
  • Erwinia species such as Erwinia amylovora.
  • the triazolopyrimidines according to the invention are preferably suitable for use against
  • legumes in particular soybean rust.
  • the term legumes includes peas, beans, lentils, peanuts, lupines and, in particular, soybeans.
  • the triazolopyrimidines according to the invention are particularly suitable for use in soybean cultivation.
  • triazolopyrimidines according to the invention are particularly suitable for use against rust diseases in soybean, in particular Phakopsora pachyrhizi or Phakopsora meibomiae.
  • the invention also provides a method for controlling diseases of legumes, in particular rust diseases in soya, wherein a triazolopyrimidine of the formula (I) is applied to the vegetable plant, its environment or its seed.
  • the good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of whole plants (above-ground parts of plants and roots), of planting and seed, and the soil.
  • the active compound combinations according to the invention can be used for foliar application or as a mordant.
  • the good plant tolerance of the usable active ingredients in the necessary concentrations for controlling plant diseases allows treatment of the seed.
  • the active compounds according to the invention can thus be used as mordants.
  • the invention therefore also relates to a process for the protection of seed and germinating plants from the infestation of phytopathogenic fungi by treating the seed with an agent according to the invention.
  • the invention also relates to the use of the seed treatment agents of the invention for protecting the seed and the germinating plant from phytopathogenic fungi.
  • the invention relates to seed which has been treated with an agent according to the invention for protection against phytopathogenic fungi.
  • One of the advantages of the invention is that because of the particular systemic properties of the agents according to the invention, the treatment of the seed with these agents protects not only the seed itself but also the resulting plants after emergence from phytopathogenic fungi. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • mixtures according to the invention can also be used in particular in the case of transgenic seed.
  • compositions according to the invention are suitable for the protection of seeds of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of soy, bean, peanut.
  • composition according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used which has been harvested, cleaned and dried to a moisture content below 15% by weight.
  • seed may also be used which, after drying, e.g. treated with water and then dried again.
  • the agents according to the invention can be applied directly, that is to say without further components, and without having been diluted. As a rule, it is preferable to use the funds in
  • Suitable formulations and Methods for seed treatment are known in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2 ,
  • Wirkstorikombinationen invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant varieties which can or can not be protected by plant variety rights.
  • Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active substances takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
  • plants and their parts can be treated.
  • wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars which have been obtained by ge ⁇ technischen methods optionally in combination with conventional methods (Genetically Modified Organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above.
  • the treatment according to the invention can also For example, reduced application rates and / or enhancements of the spectrum of action and / or enhancement of the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or against water or soil salt content, increased flowering power, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects.
  • the preferred plants or plant cultivars to be treated according to the invention include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits") Examples of such properties are better plant growth. increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances. Soya may be mentioned as examples of transgenic plants.
  • Traits which are particularly emphasized are the increased defense of the plants against insects by toxins which are formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CryHIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) are produced in the plants (hereinafter "Bt plants”).
  • Bt plants Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT" gene).
  • traits can occur together in the transgenic plants in combination.
  • “Bt plants” soybean varieties may be mentioned, which are sold under the trade names YIELD GARD ® (eg soy).
  • Examples of herbicide-tolerant plants soybean varieties may be mentioned, which are sold under the trade names Roundup Ready ® (tolerance to glyphosate, for example soybeans), IMI ®.
  • Roundup Ready ® tolerance to glyphosate, for example soybeans
  • IMI ® As herbicide-resistant (conventionally grown on herbicide tolerance) plants are also mentioned the varieties sold under the name Clearfield ® .
  • Clearfield ® As herbicide-resistant (conventionally grown on herbicide tolerance) plants are also mentioned the varieties sold under the name Clearfield ® .
  • the triazolopyrimidines according to the invention may additionally contain further fungicidal, bactericidal or insecticidal components.
  • Azoxystrobin Cyazofamide, Ditnoxystrobin, Enestrobin, Famoxadone, Fenamidone, Fluoxastrobin, Kresoximmethyl, Metominostrobin, Oiysastrobin, Pyraclostrobin, Picoxystrobin, Trifloxystrobin
  • carbamates eg alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, azamethiphos, bendocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carboofuran, carbosulfane, chloethocarb, coumaphos, cyanofenphos, cyanophos, dimetilane, ethiofencarb, fenobucarb, Fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb)
  • organophosphates eg acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinophos, chloroforms, chlorpyrifos (-methyl / -ethyl), Coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphone, dialifos, diazinon, dichlofenthione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulphoton, EPN, ethion, ethoprophos, etrimfos, Fam- phur, Fenamiphos
  • Pyrethroids eg acrinathrin, aethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, biotethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chovaporthrin, cis-cypermethrin , Cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, DDT, deltamethrin, empenthrin (IR-isomer), esfenvalerate, etofenprox , Fenfluthrin,
  • Oxadiazines e.g., indoxacarb
  • chloronicotinyls / neonicotinoids for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, tenpyram, nithiazines, thiacloprid, thiamethoxam
  • Fiproles e.g., acetoprole, ethiprole, fipronil, vaniliprole
  • Mectins e.g., abamectin, avermectin, emamectin, emamectin benzoate, ivnectin, milbemectin, milbemycin
  • diacylhydrazines e.g., chromafenozides, halofenozides, methoxyfenozides, tebufenozides
  • Benzoylureas eg, Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, FhicycloxurorL, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penflurone, Teflubenzuron, Trivoluron
  • Buprofezin eg, Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, FhicycloxurorL, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penflurone, Teflubenzuron, Trivoluron
  • Organotin e.g., azocyclotin, cyhexatin, fenbutatin oxides
  • METTs e.g., Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • Tetronic acids e.g., spirodiclofen, spiromesifen
  • 16.2 tetramic acids [eg 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (also known as: carbonic acid, 3- (2, 5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec- 3-en-4-yl ethyl ester, CAS Reg.
  • fumigants e.g., aluminum phosphides, methyl bromides, sulfuryl fluorides
  • mite growth inhibitors e.g., clofentezine, etoxazole, hexythiazox
  • a mixture with other known active substances, such as herbicides, safeners or semiochemicals, or with fertilizers and growth regulators is possible.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension-emulsion concentrates, Active substance-impregnated natural and synthetic substances as well as ultra-fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV-KaIt and warm mist formulations.
  • the customary formulations such as solutions, emulsions, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension-emulsion concentrates, Active substance-impregnated natural and synthetic substances as well as ultra-fine encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV-KaIt and warm mist formulations.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds or the active compound combinations with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • liquefied gaseous diluents or carriers are meant those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates.
  • ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • ground synthetic minerals such as fumed silica, alumina and silicates.
  • Carriers for granules are suitable: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates.
  • Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
  • adhesives such as carboxymethylcellulose, naturhche and synthetic powdery, gromige or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and meta-phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and meta-phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the active ingredient content of the use forms prepared from the commercial formulations can vary widely.
  • the active ingredient concentration of the use forms for controlling animal pests such as insects and acarids may be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
  • the application is done in a custom forms adapted to the application forms.
  • the formulations for controlling phytopathogenic fungi generally contain between 0.1 and 95% by weight of active substances, preferably between 0.5 and 90%.
  • the active compounds used according to the invention can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders, dusts and granules.
  • the application is done in the usual way, e.g. by pouring (drenchen), drip irrigation, spraying, spraying, scattering, dusting, foaming, brushing, spreading, dry pickling, wet pickling, wet pickling, slurry pickling, encrusting, etc.
  • the active compounds according to the invention can be present in commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the application rates can be varied within a substantial range, depending on the mode of application.
  • the application rates of active ingredients are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the application rates of active ingredient combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of active ingredient combination are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, and other Verstellverngshüfsrnitteln.
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at about 21 0 C and a relative humidity of about 90%.
  • the compounds according to the invention listed in Examples 1, 3, 156, 238, 264, 271 and 274 exhibit an efficacy of 70% or more at an active ingredient concentration of 100 ppm.
  • Emulsifier 1.5 parts by weight of polyoxyethyl dialkyl phenyl ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the compounds of the invention listed in Examples 1, 2, 3, 115, 156 show an efficiency of 80% or more at an active ingredient concentration of 100 ppm.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

La présente invention concerne des triazolopyrimidines de formule générale (I) dans laquelle R1, R2, R3, R4, R5, R6, R7 et R8 ont les correspondances indiquées dans la description. Ces triazolopyrimidines conviennent très bien au traitement des maladies de rouilles chez les légumineuses.
EP06753926A 2005-06-08 2006-05-26 Utilisation de triazolopyrimidines pour reguler les phytopathologies chez les legumineuses Withdrawn EP1893021A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005026577A DE102005026577A1 (de) 2005-06-08 2005-06-08 Verwendung von Triazolopyrimidinen zur Kontrolle von Pflanzenkrankheiten an Hülsenfrüchten
PCT/EP2006/005073 WO2006131223A2 (fr) 2005-06-08 2006-05-26 Utilisation de triazolopyrimidines pour reguler les phytopathologies chez les legumineuses

Publications (1)

Publication Number Publication Date
EP1893021A2 true EP1893021A2 (fr) 2008-03-05

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EP06753926A Withdrawn EP1893021A2 (fr) 2005-06-08 2006-05-26 Utilisation de triazolopyrimidines pour reguler les phytopathologies chez les legumineuses

Country Status (10)

Country Link
US (1) US20090149455A1 (fr)
EP (1) EP1893021A2 (fr)
JP (1) JP2008545764A (fr)
KR (1) KR20080032076A (fr)
CN (1) CN101287371A (fr)
AR (1) AR053885A1 (fr)
BR (1) BRPI0612029A2 (fr)
DE (1) DE102005026577A1 (fr)
TW (1) TW200715970A (fr)
WO (1) WO2006131223A2 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4272417A (en) * 1979-05-22 1981-06-09 Cargill, Incorporated Stable protective seed coating
US4245432A (en) * 1979-07-25 1981-01-20 Eastman Kodak Company Seed coatings
US4808430A (en) * 1987-02-27 1989-02-28 Yazaki Corporation Method of applying gel coating to plant seeds
US5876739A (en) * 1996-06-13 1999-03-02 Novartis Ag Insecticidal seed coating
TW460476B (en) * 1997-04-14 2001-10-21 American Cyanamid Co Fungicidal trifluoromethylalkylamino-triazolopyrimidines
US5994360A (en) * 1997-07-14 1999-11-30 American Cyanamid Company Fungicidal 5-alkyl-triazolopyrimidines
JP2000119274A (ja) * 1998-08-13 2000-04-25 Nippon Bayer Agrochem Co Ltd トリアゾロピリミジン誘導体
US6117865A (en) * 1998-09-10 2000-09-12 American Cyanamid Company Fungicidal trifluorophenyl-triazolopyrimidines
US6503904B2 (en) * 1998-11-16 2003-01-07 Syngenta Crop Protection, Inc. Pesticidal composition for seed treatment
AU2002221831A1 (en) * 2000-11-13 2002-05-21 Basf Aktiengesellschaft 7-(r)-amino-triazolopyrimidines, the production thereof and use of the same for combating phytopathogenic fungi
DE10121102A1 (de) * 2001-04-27 2002-11-07 Bayer Ag Triazolopyrimidine
DE10218592A1 (de) * 2002-04-26 2003-11-06 Bayer Cropscience Ag Triazolopyrimidine
JP2005530756A (ja) * 2002-05-03 2005-10-13 ビーエーエスエフ アクチェンゲゼルシャフト 殺菌性トリアゾロピリミジン、その製造方法、及び有害菌類の抑制のためのその使用、ならびにこれを含む組成物
BRPI0408864A (pt) * 2003-04-02 2006-04-11 Basf Ag compostos, processo para a preparação de um composto, preparação adequada para o controle de fungos danosos e processo para o controle de fungos fitopatogênicos danosos

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006131223A2 *

Also Published As

Publication number Publication date
AR053885A1 (es) 2007-05-23
BRPI0612029A2 (pt) 2010-10-13
US20090149455A1 (en) 2009-06-11
CN101287371A (zh) 2008-10-15
KR20080032076A (ko) 2008-04-14
TW200715970A (en) 2007-05-01
JP2008545764A (ja) 2008-12-18
WO2006131223A2 (fr) 2006-12-14
WO2006131223A3 (fr) 2007-08-23
DE102005026577A1 (de) 2006-12-14

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