EP1727431A2 - Fungicidal mixtures made from a triazolopyrimidine derivative - Google Patents

Fungicidal mixtures made from a triazolopyrimidine derivative

Info

Publication number
EP1727431A2
EP1727431A2 EP05736846A EP05736846A EP1727431A2 EP 1727431 A2 EP1727431 A2 EP 1727431A2 EP 05736846 A EP05736846 A EP 05736846A EP 05736846 A EP05736846 A EP 05736846A EP 1727431 A2 EP1727431 A2 EP 1727431A2
Authority
EP
European Patent Office
Prior art keywords
compound
compounds
mixtures
formula
harmful fungi
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Withdrawn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
EP05736846A
Other languages
German (de)
French (fr)
Inventor
Jordi Tormo I Blasco
Thomas Grote
Maria Scherer
Reinhard Stierl
Siegfried Strathmann
Ulrich Schöfl
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
Publication of EP1727431A2 publication Critical patent/EP1727431A2/en
Withdrawn legal-status Critical Current

Links

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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products

Definitions

  • the present invention relates to fungicidal mixtures for controlling phytopathogenic harmful fungi, comprising active components
  • the invention relates to a method for controlling harmful fungi with mixtures of the compound I with the compounds II and the use of the compound I with the compounds II for the production of such mixtures and agents which contain these mixtures.
  • EP-A 988 790 Mixtures of triazolopyrimidine derivatives with other active ingredients are generally known from EP-A 988 790 and US 6 268 371.
  • the synergistic mixtures described in EP-A 988 790 are described as being fungicidally active against various diseases of cereals, fruits and vegetables, in particular mildew on wheat and barley or gray mold on apples.
  • the mixtures known from US Pat. No. 6,268,371 are described as being particularly advantageous against rice diseases.
  • the present invention was based on mixtures which, with a reduced total amount of active compounds applied, have an improved activity against harmful fungi (synergistic mixtures).
  • the mixtures of the compound I and the compound II or the simultaneous joint or separate use of the compound I and the compound II are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromyces ten, Oomycetes and Basidiomycetes. They can be used in plant protection as leaf and soil fungicides.
  • the mixtures according to the invention are of particular importance for controlling harmful fungi on rice plants and on their seeds, such as bipolaris and woodturners, and also Pyricularia oryzae. They are particularly suitable for combating the rice brown spot disease caused by Cochliobolus miyabeanus.
  • Rhizoctonia soiani is the causative agents of the most important diseases of rice plants. Rhizoctonia soiani is the only agronomically important pathogen within the Agaricomycetidae subclass. This fungus does not attack the plant via spores like most other fungi, but via a mycelial infection.
  • the mixtures according to the invention can also be used in material protection (e.g. wood protection), for example against Paecilomyces variotii.
  • Pests such as insects, arachnids or nematodes, or herbicidal or growth-regulating active ingredients or fertilizers.
  • active substances selected from the following groups are possible as further active substances in the above sense:
  • Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • Amine derivatives such as aldimorph, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, tridemorph, anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil,
  • Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
  • Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, ipconazole, metconazol, penocolazolol, myocazolol, myocazolol, myclazol, myclazol, myclazol, myocazolol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol, myclazol , Tetraconazole, tri-dimefon, triadimenol, triflumizole, triticonazole,
  • Dicarboximides such as myclozolin,
  • Dithiocarbamates such as Ferbam, Nabam, Metam, Propineb, Polycarbamat, Ziram, Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronilonolonolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolinolonolinolinolonolinolonolinolonolinolonolimolinolonolimolonolonolimolonolonylolonylolonylolonylololate Silthiofam, thiabendazole, thifluzamide, tiadinil, tri
  • Nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitrophthal-isopropyl,
  • Phenylpyrroles such as fenpiclonil or fludioxonil
  • fungicides such as AcibenzoIar-S-methyl, Benthiavalicarb, Carpropamid, Chlo-rothalonil, Cyflufenamid, Cymoxanil, Diclomezin, Diclocymet, Diethofencarb, Edifenphos, Ethaboxam, Fenhexamid, Fentin-Acetate, Fenoxanyl, namim, Fosinzone, Fluorozone, Fluorozone Fosetyl aluminum, phosphorous acid, iprovalicarb, hexachlorobenzene, metrafenone, methyl isothiocyanate, pencycuron, propamocarb, phthalide, toloclo-fos-methyl, quintozene, zoxamide, • strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, cromostoximrobin, kromostoximrobin, kresost Pyraclo
  • Sulfenic acid derivatives such as captafol, captan, diclofluanid, folpet,
  • Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • a further fungicide III or two fungicides III and IV are added to the compounds I and II.
  • the compound I and the compound II can be applied simultaneously together or separately or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures.
  • the compound I and the compound II are usually used in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:50, in particular 10: 1 to 1:10.
  • Components III and IV are optionally mixed in a ratio of 20: 1 to 1:20 to the compounds I.
  • the application rates of the mixtures according to the invention are 5 g / ha to 1000 g / ha, preferably 50 to 850 g / ha, in particular 50 to 750 g / ha.
  • the application rates for the compound I are generally from 1 to 1000 g / ha, preferably from 10 to 750 g / ha, in particular from 20 to 500 g / ha.
  • the application rates for compound II are generally from 1 to 1000 g / ha, preferably from 10 to 750 g / ha, in particular from 20 to 500 g / ha.
  • application rates of mixture of 1 to 1000 g / 100 kg of seed preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg, are generally used.
  • the compounds I and II (and possibly III and IV) or the mixtures of the compounds I and II (and possibly III and IV) are applied separately or together by spraying or dusting the seeds , seedlings, plants or soils before or after sowing the plants or before or after emergence of the plants.
  • Application is preferably carried out by spraying the leaves.
  • the compounds can be applied jointly or separately by applying granules or by dusting the floors.
  • the mixtures according to the invention, or the compounds I and II, can be converted into the customary formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should 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.
  • solvents / auxiliaries water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example petroleum fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butryolactone) , Pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • aromatic solvents for example Solvesso products, xylene
  • paraffins for example petroleum fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamm
  • solvent mixtures can also be used, carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl
  • Alkali, alkaline earth, and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid come as surface-active substances, Alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers are used, furthermore condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of
  • Castor oil polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin sulfite waste liquors and methyl cellulose.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil, furthermore coal tar oils as well as 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, strongly polar solvents, e.g. Dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil
  • coal tar oils as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, 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, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics,
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredients.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • Suspensions 20 parts by weight of the active ingredients are comminuted in a stirred ball mill to form a fine active ingredient suspension with the addition of dispersing and wetting agents and water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredients are finely ground with the addition of dispersing and wetting agents and produced using technical equipment (e.g. 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.
  • technical equipment e.g. extrusion, spray tower, fluidized bed
  • WP, SP Water-dispersible and water-soluble powders 75 parts by weight of the active ingredients are ground in a rotor-strator mill with the addition of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredients as such in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the purposes; 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.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. 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 process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention, which is usually done in a weight ratio of 1:10 to 10: 1.
  • the compounds I and II, or the mixtures or the corresponding formulations are used in that the harmful fungi, the plants, seeds, soils, soils, areas, materials or spaces to be kept free from them are mixed with an amount of the mixture which is fungicidal, or of compounds I and II treated separately.
  • the application can take place before or after the infestation by the harmful fungi.
  • the fungicidal activity of the compound and the mixtures can be demonstrated by the following tests:
  • the active ingredients were prepared separately or together as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO. 1% by weight of Uniperol® EL emulsifier (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
  • Uniperol® EL emulsifier wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • Leaves of 'Tai-Nong 67' rice seedlings grown in pots were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. The following day, the plants were inoculated with an aqueous spore suspension of Cochliobolus miyabeanus. The test plants were then used set up in climatic chambers at 22 - 24 ° C and 95 - 99% relative humidity for 6 days, then the extent of the development of the infestation on the leaves was determined visually.
  • the evaluation is carried out by determining the affected leaf areas in percent. These percentages were converted into efficiencies.
  • ⁇ corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
  • ß corresponds to the fungal attack of the untreated (control) plants in%
  • the infection of the treated plants corresponds to that of the untreated control plants; with an efficiency of 100, the treated plants show no infection.
  • the expected efficacies of the active ingredient mixtures are determined using the Colby formula [RS Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficiencies.

Abstract

The invention relates to fungicidal mixtures containing in the form of active agents: a triazolopyrimidine derivative of formula (I) and thiophanate-methyl of formula (II) in synergistically active quantity and to a method for controlling harmful fungi by means of the mixture of the compounds I and II, thereby making it possible to produce said mixtures and the products containing them.

Description

Fungizide MischungenFungicidal mixtures
Beschreibungdescription
Die vorliegende Erfindung betrifft fungizide Mischungen zur Bekämpfung von pflanzen- pathogenen Schadpilzen, enthaltend als aktive KomponentenThe present invention relates to fungicidal mixtures for controlling phytopathogenic harmful fungi, comprising active components
1 ) das Triazolopyrimidinderivat der Formel I,1) the triazolopyrimidine derivative of the formula I,
und and
2) Thiophanate-Methyl der Formel II,2) thiophanate-methyl of the formula II,
in einer synergistisch wirksamen Menge.in a synergistically effective amount.
Außerdem betrifft die Erfindung ein Verfahren zur Bekämpfung von Schadpilzen mit Mischungen der Verbindung I mit den Verbindungen II und die Verwendung der Verbindung I mit den Verbindungen II zur Herstellung derartiger Mischungen sowie Mittel, die diese Mischungen enthalten.In addition, the invention relates to a method for controlling harmful fungi with mixtures of the compound I with the compounds II and the use of the compound I with the compounds II for the production of such mixtures and agents which contain these mixtures.
Die Verbindung I, 5-Chlor-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluor-phenyi)-[1 ,2,4]tri- azolo[1,5-a]pyrimidin, ihre Herstellung und deren Wirkung gegen Schadpilze ist aus der Literatur bekannt (WO 98/46607).The compound I, 5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyi) - [1, 2.4] tri-azolo [1.5 -a] pyrimidine, its preparation and its action against harmful fungi is known from the literature (WO 98/46607).
Die Verbindung II, 1 ,2-PhenyIenbis(iminocarbonothioyl)bis(dimethylcarbamat), ihre Herstellung und deren Wirkung gegen Schadpilze ist ebenfalls aus der Literatur bekannt (DE-OS 19 30 540; common name: Thiophanate-Methyl).The compound II, 1, 2-PhenyIenbis (iminocarbonothioyl) bis (dimethylcarbamate), their preparation and their action against harmful fungi is also known from the literature (DE-OS 19 30 540; common name: Thiophanate-Methyl).
Mischungen von Triazolopyrimidinderivaten mit anderen Wirkstoffen sind allgemein aus EP-A 988 790 und US 6 268 371 bekannt. Die in EP-A 988 790 beschriebenen synergistischen Mischungen werden als fungizid wirksam gegen verschiedene Krankheiten von Getreide, Obst und Gemüse, insbesondere Mehltau an Weizen und Gerste oder Grauschimmel an Äpfeln beschrieben. Die aus US 6 268 371 bekannten Mischungen werden als besonders vorteilhaft gegen Reiskrankheiten einsetzbar beschrieben.Mixtures of triazolopyrimidine derivatives with other active ingredients are generally known from EP-A 988 790 and US 6 268 371. The synergistic mixtures described in EP-A 988 790 are described as being fungicidally active against various diseases of cereals, fruits and vegetables, in particular mildew on wheat and barley or gray mold on apples. The mixtures known from US Pat. No. 6,268,371 are described as being particularly advantageous against rice diseases.
Im Hinblick auf eine wirkungsvolle Bekämpfung von Schadpilzen bei möglichst geringen Aufwandmengen lagen der vorliegenden Erfindungen Mischungen als Aufgabe zugrunde, die bei verringerter Gesamtmenge an ausgebrachten Wirkstoffen eine ver- besserte Wirkung gegen Schadpilze zeigen (synergistische Mischungen).In view of an effective control of harmful fungi at the lowest possible application rates, the present invention was based on mixtures which, with a reduced total amount of active compounds applied, have an improved activity against harmful fungi (synergistic mixtures).
Demgemäss wurden die eingangs definierten Mischungen gefunden. Es wurde außerdem gefunden, dass sich bei gleichzeitiger gemeinsamer oder getrennter Anwendung der Verbindung I und der Verbindung II oder bei Anwendung der Verbindungen I und der Verbindung II nacheinander Schadpilze, insbesondere Reispathogene, besser bekämpfen lassen als mit den Einzelverbindungen.Accordingly, the mixtures defined at the outset were found. It has also been found that, when the compound I and the compound II are used simultaneously or separately, or when the compounds I and the compound II are used in succession, harmful fungi, in particular rice pathogens, can be controlled better than with the individual compounds.
Die Mischungen der Verbindung I und der Verbindung II bzw. die gleichzeitige gemeinsame oder getrennte Verwendung der Verbindung I und der Verbindung II zeichnen sich aus durch eine hervorragende Wirksamkeit gegen ein breites Spektrum von pflan- zenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten, Deuteromyce- ten, Oomyceten und Basidiomyceten. Sie können im Pflanzenschutz als Blatt- und Bodenfungizide eingesetzt werden.The mixtures of the compound I and the compound II or the simultaneous joint or separate use of the compound I and the compound II are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromyces ten, Oomycetes and Basidiomycetes. They can be used in plant protection as leaf and soil fungicides.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Bananen, Baumwolle, Gemüsepflanzen (z.B. Gurken, Bohnen und Kürbisgewächse), Gerste, Gras, Hafer, Kaffee, Kartoffeln, Mais, Obstpflanzen, Reis, Roggen, Soja, Tomaten, Wein, Weizen, Zierpflanzen, Zuckerrohr und einer Vielzahl von Samen.They are particularly important for combating a large number of fungi on various crops such as bananas, cotton, vegetables (e.g. cucumbers, beans and squashes), barley, grass, oats, coffee, potatoes, corn, fruit plants, rice, rye, soybeans, tomatoes , Wine, wheat, ornamental plants, sugar cane and a variety of seeds.
Vorteilhaft eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Blumeria graminis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphae- rotheca fuliginea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncinula necatoran Reben, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Aften an Getreide und Zuckerrohr, Venturia inaequalis an Äpfeln, Bipolaris- und Drechslera-Aήen an Getreide, Reis und Rasen, Septoria nodorum an Weizen, Botrytis cinerea an Erdbeeren, Gemüse, Zierpflanzen und Reben, My- cosphaerella-Avten an Bananen, Erdnüssen und Getreide, Pseudocercosporella her- potrichoides an Weizen und Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Pseudoperonospora-Aüen an Kürbisgewächsen und Hop- fen, Plasmopara viticola an Reben, Alternaria-Aήen an Gemüse und Obst sowie Fusa- rium- und Verticillium-Aύen.They are advantageously suitable for combating the following phytopathogenic fungi: Blumeria graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphae-rotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necatoran vines, Puccinia cotton species on cereal species, Rhiz , Rice and lawn, Ustilago-Aften on cereals and sugar cane, Venturia inaequalis on apples, Bipolaris and Drechslera-Aήen on cereals, rice and lawn, Septoria nodorum on wheat, Botrytis cinerea on strawberries, vegetables, ornamental plants and vines, Mycosphaerella -Avten on bananas, peanuts and cereals, Pseudocercosporella her- potrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Pseudoperonospora outside on pumpkin plants and hop- fen, Plasmopara viticola on vines, Alternaria Aήs on vegetables and fruits and Fusarium and Verticillium Aύs.
Besondere Bedeutung haben die erfindungsgemäßen Mischungen für die Bekämpfung von Schadpilzen an Reispflanzen und an deren Saatgut, wie Bipolaris- und Drechslera- Arten, sowie Pyricularia oryzae. Insbesondere eignen sie sich zur Bekämpfung der Braunfleckenkrankheit des Reises, die durch Cochliobolus miyabeanus verursacht wird.The mixtures according to the invention are of particular importance for controlling harmful fungi on rice plants and on their seeds, such as bipolaris and woodturners, and also Pyricularia oryzae. They are particularly suitable for combating the rice brown spot disease caused by Cochliobolus miyabeanus.
In Reis sind andere Pathogene typisch als in Getreide oder Obst. Pyricularia oryzae und Corticium sasakii (syn. Rhizoctonia soiani) sind die Erreger der bedeutendsten Krankheiten von Reispflanzen. Rhizoctonia soiani ist das einzige landwirtschaftlich bedeutende Pathogen innerhalb der Unterklasse Agaricomycetidae. Dieser Pilz befällt die Pflanze nicht wie die meisten anderen Pilze über Sporen, sondern über eine Myzelinfektion.Other pathogens are typical in rice than in cereals or fruit. Pyricularia oryzae and Corticium sasakii (syn. Rhizoctonia soiani) are the causative agents of the most important diseases of rice plants. Rhizoctonia soiani is the only agronomically important pathogen within the Agaricomycetidae subclass. This fungus does not attack the plant via spores like most other fungi, but via a mycelial infection.
Die erfindungsgemäßen Mischungen sind außerdem im Materialschutz (z.B. Holzschutz) anwendbar, beispielsweise gegen Paecilomyces variotii.The mixtures according to the invention can also be used in material protection (e.g. wood protection), for example against Paecilomyces variotii.
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe I und II ein, denen man je nach Bedarf weitere Wirkstoffe gegen Schadpilze oder andereWhen preparing the mixtures, preference is given to using the pure active ingredients I and II, to which, depending on the need, further active ingredients against harmful fungi or others
Schädlinge wie Insekten, Spinntiere oder Nematoden, oder auch herbizide oder wachstumsregulierende Wirkstoffe oder Düngemittel beimischen kann.Pests such as insects, arachnids or nematodes, or herbicidal or growth-regulating active ingredients or fertilizers.
Als weitere Wirkstoffe im voranstehenden Sinne kommen insbesondere Wirkstoffe ausgewählt aus den folgenden Gruppen in Frage:In particular, active substances selected from the following groups are possible as further active substances in the above sense:
• Acylalanine wie Benalaxyl, Metalaxyl, Ofurace, Oxadixyl,Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
• Aminderivate wie Aldimorph, Dodemorph, Fenpropimorph, Fenpropidin, Guazatine, Iminoctadine, Tridemorph, • Anilinopyrimidine wie Pyrimethanil, Mepanipyrim oder Cyprodinil,Amine derivatives such as aldimorph, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, tridemorph, anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil,
• Antibiotika wie Cycloheximid, Griseofulvin, Kasugamycin, Natamycin, Polyoxin oder Streptomycin,Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
• Azole wie Bitertanol, Bromoconazol, Cyproconazol, Difenoconazole, Dinitrocona- zol, Enilconazol, Epoxiconazol, Fenbuconazol, Fluquiconazol, Flusilazol, Flutriafol, Hexaconazol, Imazalil, Ipconazol, Metconazol, Myclobutanil, Penconazol, Propico- nazol, Prochloraz, Prothioconazol, Simeconazol, Tebuconazol, Tetraconazol, Tria- dimefon, Triadimenol, Triflumizol, Triticonazol,Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, ipconazole, metconazol, penocolazolol, myocazolol, myocazolol, myclazol, myclazol, myclazol, myocazolol, myclazol, myclazol, myclazol, myclazol, myclazol , Tetraconazole, tri-dimefon, triadimenol, triflumizole, triticonazole,
• Dicarboximide wie Myclozolin,Dicarboximides such as myclozolin,
• Dithiocarbamate wie Ferbam, Nabam, Metam, Propineb, Polycarbamat, Ziram, • Heterocylische Verbindungen wie Anilazin, Benomyl, Boscalid, Carbendazim, Car- boxin, Oxycarboxin, Cyazofamid, Dazomet, Dithianon, Famoxadon, Fenamidon, Fenarimol, Fuberidazol, Flutolanil, Furametpyr, Isoprothiolan, Mepronil, Nuarimol, Penthiopyrad, Probenazol, Pyroquilon, Quinoxyfen, Silthiofam, Thiabendazol, Thifluzamid, Tiadinil, Tricyclazol, Triforine,Dithiocarbamates such as Ferbam, Nabam, Metam, Propineb, Polycarbamat, Ziram, Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronilonolonolinolinolinolinolinolonolinolinolinolinolinolinolinolinolonolinolinolonolinolinolonolinolonolinolonolinolonolinolonolinolonolinolonolonolimolinolonolimolonolonylolonylolonylolonylolate Silthiofam, thiabendazole, thifluzamide, tiadinil, tricyclazole, triforine,
• Nitrophenylderivate, wie Binapacryl, Dinocap, Dinobuton, Nitrophthal-isopropyl,Nitrophenyl derivatives, such as binapacryl, dinocap, dinobutone, nitrophthal-isopropyl,
• Phenylpyrrole wie Fenpiclonil oder Fludioxonil,Phenylpyrroles such as fenpiclonil or fludioxonil,
• Schwefel oder Kupferfungizide,Sulfur or copper fungicides,
• Sonstige Fungizide wie AcibenzoIar-S-methyl, Benthiavalicarb, Carpropamid, Chlo- rothalonil, Cyflufenamid, Cymoxanil, Diclomezin, Diclocymet, Diethofencarb, Edi- fenphos, Ethaboxam, Fenhexamid, Fentin-Acetat, Fenoxanil, Ferimzone, Fluazi- nam, Fosetyl, Fosetyl-Aluminium, Phosphorige Säure, Iprovalicarb, Hexachlorben- zol, Metrafenon, Methylisothiocyanat, Pencycuron, Propamocarb, Phthalid, Toloclo- fos-methyl, Quintozene, Zoxamid, • Strobilurine wie Azoxystrobin, Dimoxystrobin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Pyraclostrobin oder Trifloxystrobin,• Other fungicides such as AcibenzoIar-S-methyl, Benthiavalicarb, Carpropamid, Chlo-rothalonil, Cyflufenamid, Cymoxanil, Diclomezin, Diclocymet, Diethofencarb, Edifenphos, Ethaboxam, Fenhexamid, Fentin-Acetate, Fenoxanyl, namim, Fosinzone, Fluorozone, Fluorozone Fosetyl aluminum, phosphorous acid, iprovalicarb, hexachlorobenzene, metrafenone, methyl isothiocyanate, pencycuron, propamocarb, phthalide, toloclo-fos-methyl, quintozene, zoxamide, • strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, cromostoximrobin, kromostoximrobin, kresost Pyraclostrobin or trifloxystrobin,
• Sulfensäurederivate wie Captafol, Captan, Diclofluanid, Folpet,Sulfenic acid derivatives such as captafol, captan, diclofluanid, folpet,
• Zimtsäurearnide und Analoge wie Dimethomorph, Flumetover oder Flumorph.• Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
In einer Ausführungsform der erfindungsgemäßen Mischungen werden den Verbindungen I und II ein weiteres Fungizid III oder zwei Fungizide III und IV beigemischt.In one embodiment of the mixtures according to the invention, a further fungicide III or two fungicides III and IV are added to the compounds I and II.
Die Verbindung I und die Verbindung II (und ggf. IM und IV) können gleichzeitig gemeinsam oder getrennt oder nacheinander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat.The compound I and the compound II (and possibly IM and IV) can be applied simultaneously together or separately or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures.
Die Verbindung I und die Verbindung II werden üblicherweise in einem Gewichtsverhältnis von 100:1 bis 1:100, vorzugsweise 20:1 bis 1:50, insbesondere 10:1 bis 1:10 angewandt.The compound I and the compound II are usually used in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:50, in particular 10: 1 to 1:10.
Die Komponenten III und IV werden ggf. im Verhältnis von 20:1 bis 1 :20 zu den Verbindungen I zugemischt.Components III and IV are optionally mixed in a ratio of 20: 1 to 1:20 to the compounds I.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen je nach Art der Verbindung und des gewünschten Effekts bei 5 g/ha bis 1000 g/ha, vorzugsweise 50 bis 850 g/ha, insbesondere 50 bis 750 g/ha.Depending on the type of compound and the desired effect, the application rates of the mixtures according to the invention are 5 g / ha to 1000 g / ha, preferably 50 to 850 g / ha, in particular 50 to 750 g / ha.
Die Aufwandmengen für die Verbindung I liegen entsprechend in der Regel bei 1 bis 1000 g/ha, vorzugsweise 10 bis 750 g/ha, insbesondere 20 bis 500 g/ha. Die Aufwandmengen für die Verbindung II liegen entsprechend in der Regel bei 1 bis 1000 g/ha, vorzugsweise 10 bis 750 g/ha, insbesondere 20 bis 500 g/ha.Accordingly, the application rates for the compound I are generally from 1 to 1000 g / ha, preferably from 10 to 750 g / ha, in particular from 20 to 500 g / ha. Correspondingly, the application rates for compound II are generally from 1 to 1000 g / ha, preferably from 10 to 750 g / ha, in particular from 20 to 500 g / ha.
Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 1 bis 1000 g/100 kg Saatgut, vorzugsweise 1 bis 200 g/100 kg, insbesondere 5 bis 100 g/100 kg verwendet.In the case of seed treatment, application rates of mixture of 1 to 1000 g / 100 kg of seed, preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg, are generally used.
Bei der Bekämpfung von für Pflanzen pathogener Schadpilze erfolgt die getrennte oder gemeinsame Applikation der Verbindungen I und II (und ggf. III und IV) oder der Mischungen aus den Verbindungen I und II (und ggf. III und IV) durch Besprühen oder Bestäuben der Samen, der Sämlinge, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Auflaufen der Pflanzen. Bevorzugt erfolgt die Applikation durch Besprühen der Blätter. Die Applikation der Verbindungen gemeinsam oder getrennt kann auch durch Granulatapplikation oder Bestäuben der Böden erfolgen.When combating harmful fungi which are pathogenic to plants, the compounds I and II (and possibly III and IV) or the mixtures of the compounds I and II (and possibly III and IV) are applied separately or together by spraying or dusting the seeds , seedlings, plants or soils before or after sowing the plants or before or after emergence of the plants. Application is preferably carried out by spraying the leaves. The compounds can be applied jointly or separately by applying granules or by dusting the floors.
Die erfindungsgemäßen Mischungen, bzw. die Verbindungen I und II können in die üblichen Formulierungen überführt werden, z.B. Lösungen, Emulsionen, Suspensio- nen, Stäube, Pulver, Pasten und Granulate. Die Anwendungsform richtet sich nach dem jeweiligen Verwendungszweck; sie soll in jedem Fall eine feine und gleichmäßige Verteilung der erfindungsgemäßen Verbindung gewährleisten.The mixtures according to the invention, or the compounds I and II, can be converted into the customary formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
Die Formulierungen werden in bekannter Weise hergestellt, z.B. durch Verstrecken des Wirkstoffs mit Lösungsmitteln und/oder Trägerstoffen, gewünschtenfalls unter Verwendung von Emulgiermitteln und Dispergiermitteln. Als Lösungsmittel / Hilfsstoffe kommen dafür im wesentlichen in Betracht: Wasser, aromatische Lösungsmittel (z.B. Solvesso Produkte, Xylol), Paraffine (z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol, Pentanol, Benzylalkohol), Ketone (z.B. Cyclohexanon, gamma-Butryolacton), Pyrrolidone (NMP, NOP), Aceta- te (Glykoldiacetat), Glykole, Dimethylfettsäureamide, Fettsäuren und Fettsäureester. Grundsätzlich können auch Lösungsmittelgemische verwendet werden, Trägerstoffe wie natürliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate); Emulgiermittel wie nichtionogene und anionische Emulgatoren (z.B. Polyoxyethylen- Fettalkohol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignin- Sulfitablaugen und Methylcellulose.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. The following are essentially suitable as solvents / auxiliaries: water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example petroleum fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butryolactone) , Pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters. In principle, solvent mixtures can also be used, carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
Als oberflächenaktive Stoffe kommen Alkali-, Erdalkali-, Ammoniumsalze von Ligninsul- fonsäure, Naphthalinsulfonsäure, Phenolsulfonsäure, Dibutylnaphthalinsulfonsäure, Alkylarylsulfonate, Alkylsulfate, Alkylsulfonate, Fettalkoholsulfate, Fettsäuren und sulfa- tierte Fettalkoholglykolether zum Einsatz, ferner Kondensationsprodukte von sulfonier- tem Naphthalin und Naphthalinderivaten mit Formaldehyd, Kondensationsprodukte desAlkali, alkaline earth, and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid come as surface-active substances, Alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers are used, furthermore condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of
Naphthalins bzw. der Naphtalinsulfonsäure mit Phenol und Formaldehyd, Polyoxyethy- lenoctylphenolether, ethoxyliertes Isooctylphenol, Octylphenol, Nonylphenol, Alkylphe- nolpolyglykolether, Tributylphenylpolyglykolether, Tristerylphenylpolyglykolether, Alkyl- arylpolyetheralkohole, Alkohol- und Fettalkoholethylenoxid-Kondensate, ethoxyliertesNaphthalene or the naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, tristerylphenyl polyglycol ether, alkyl aryl ethoxylated polyether fatty alcohols, alcohol alcohol ethylenepolyether fatty alcohols
Rizinusöl, Polyoxyethylenalkylether, ethoxyliertes Polyoxypropylen, Laurylalkoholpoly- glykoletheracetal, Sorbitester, Ligninsulfitablaugen und Methylcellulose in Betracht.Castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin sulfite waste liquors and methyl cellulose.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten oder Öldis- persionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kero- sin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Toluol, Xy- lol, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Methanol, Ethanol, Propanol, Butanol, Cyclohexanol, Cyclohexanon, Isophoron, stark polare Lösungsmittel, z.B. Dimethylsulfoxid, N-Methylpyrrolidon oder Wasser in Betracht.For the production of directly sprayable solutions, emulsions, pastes or oil dispersions, mineral oil fractions from medium to high boiling points, such as kerosene or diesel oil, furthermore coal tar oils as well as 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, strongly polar solvents, e.g. Dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
Pulver-, Streu- und Stäubmittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind z.B. Mineralerden, wie Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Caicium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie z.B. Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte, wie Getreidemehl, Baumrinden-, Holz- und Nussschalenmehl, Cellulosepulver und andere feste Trägerstoffe.Granules, e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, 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.
Die Formulierungen enthalten im allgemeinen zwischen 0,01 und 95 Gew.-%, vorzugsweise zwischen 0,1 und 90 Gew.-% der Wirkstoffe. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt.The formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredients. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
Beispiele für Formulierungen sind: 1. Produkte zur Verdünnung in WasserExamples of formulations are: 1. Products for dilution in water
A) Wasserlösliche Konzentrate (SL)A) Water-soluble concentrates (SL)
10 Gew. -Teile der Wirkstoffe werden in Wasser oder einem wasserlöslichen Lösungs- mittel gelöst. Alternativ werden Netzmittel oder andere Hilfsmittel zugefügt. Bei der Verdünnung in Wasser löst sich der Wirkstoff.10 parts by weight of the active ingredients are dissolved in water or a water-soluble medium solved. Alternatively, wetting agents or other aids are added. The active ingredient dissolves when diluted in water.
B) Dispergierbare Konzentrate (DC)B) Dispersible concentrates (DC)
20 Gew.-Teile der Wirkstoffe werden in Cyclohexanon unter Zusatz eines Dispergier- mittels z.B. Polyvinylpyrrolidon gelöst. Bei Verdünnung in Wasser ergibt sich eine Dispersion.20 parts by weight of the active ingredients are dissolved in cyclohexanone with the addition of a dispersing agent e.g. Dissolved polyvinyl pyrrolidone. When diluted in water, a dispersion results.
C) Emulgierbare Konzentrate (EC)C) Emulsifiable concentrates (EC)
15 Gew.-Teile der Wirkstoffe werden in Xylol unter Zusatz von Ca-Dodecylbenzol- sulfonat und Ricinusölethoxylat (jeweils 5 %) gelöst. Bei der Verdünnung in Wasser ergibt sich eine Emulsion.15 parts by weight of the active ingredients are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5% each). Dilution in water results in an emulsion.
D) Emulsionen (EW, EO)D) Emulsions (EW, EO)
40 Gew.-Teile der Wirkstoffe werden in Xylol unter Zusatz von Ca-Dodecylbenzol- sulfonat und Ricinusölethoxylat Oeweils 5 %) gelöst. Diese Mischung wird mittels einer Emulgiermaschine (Ultraturax) in Wasser eingebracht und zu einer homogenen Emulsion gebracht. Bei der Verdünnung in Wasser ergibt sich eine Emulsion.40 parts by weight of the active ingredients are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5% in each case). This mixture is introduced into water using an emulsifying machine (Ultraturax) and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
E) Suspensionen (SC, OD) 20 Gew.-Teile der Wirkstoffe werden unter Zusatz von Dispergier- und Netzmitteln und Wasser oder einem organischen Lösungsmittel in einer Rührwerkskugelmühle zu einer feinen Wirkstoffsuspension zerkleinert. Bei der Verdünnung in Wasser ergibt sich eine stabile Suspension des Wirkstoffs.E) Suspensions (SC, OD) 20 parts by weight of the active ingredients are comminuted in a stirred ball mill to form a fine active ingredient suspension with the addition of dispersing and wetting agents and water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient.
F) Wasserdispergierbare und wasserlösliche Granulate (WG, SG)F) Water-dispersible and water-soluble granules (WG, SG)
50 Gew.-Teile der Wirkstoffe werden unter Zusatz von Dispergier- und Netzmitteln fein gemahlen und mittels technischer Geräte (z.B. Extrusion, Sprühturm, Wirbelschicht) als wasserdispergierbare oder wasserlösliche Granulate hergestellt. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs.50 parts by weight of the active ingredients are finely ground with the addition of dispersing and wetting agents and produced using technical equipment (e.g. 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.
G) Wasserdispergierbare und wasserlösliche Pulver (WP, SP) 75 Gew.-Teile der Wirkstoffe werden unter Zusatz von Dispergier- und Netzmitteln sowie Kieselsäuregel in einer Rotor-Strator Mühle vermählen. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs.G) Water-dispersible and water-soluble powders (WP, SP) 75 parts by weight of the active ingredients are ground in a rotor-strator mill with the addition of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
2. Produkte für die Direktapplikation2. Products for direct application
H) Stäube (DP)H) dusts (DP)
5 Gew.Teile der Wirkstoffe werden fein gemahlen und mit 95 % feinteiligem Kaolin in- nig vermischt. Man erhält dadurch ein Stäubmittel. I) Granulate (GR, FG, GG, MG)5 parts by weight of the active ingredients are ground finely and mixed internally with 95% finely divided kaolin. This gives a dust. I) Granules (GR, FG, GG, MG)
0.5 Gew-Teile der Wirkstoffe werden fein gemahlen und mit 95.5 % Trägerstoffe verbunden. Gängige Verfahren sind dabei die Extrusion, die Sprühtrocknung oder die Wirbelschicht. Man erhält dadurch ein Granulat für die Direktapplikation.0.5 part by weight of the active ingredients are finely ground and combined with 95.5% carriers. Common processes are extrusion, spray drying or fluidized bed. This gives granules for direct application.
J) ULV- Lösungen (UL)J) ULV solutions (UL)
10 Gew.-Teile der Wirkstoffe werden in einem organischen Lösungsmittel z.B. Xylol gelöst. Dadurch erhält man ein Produkt für die Direktapplikation.10 parts by weight of the active ingredients are dissolved in an organic solvent e.g. Xylene dissolved. This gives you a product for direct application.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, z.B. in Form von direkt versprühbaren Lösungen, Pulvern, Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubmitteln, Streumitteln, Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The active ingredients as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring. The application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Wässrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netz- baren Pulvern (Spritzpulver, Öldispersionen) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Substanzen als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermitttel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz Netz-, Haft-, Dispergier- oder Emulgiermittel und even- tuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates composed of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden. Im allgemeinen liegen sie zwischen 0,0001 und 10%, vorzugsweise zwischen 0,01 und 1%.The active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wobei es möglich ist, Formulierungen mit mehr als 95 Gew.-% Wirkstoff oder sogar den Wirkstoff ohne Zusätze auszubringen.The active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
Zu den Wirkstoffen können Öle verschiedenen Typs, Netzmittel, Adjuvants, Herbizide, Fungizide, andere Schädlingsbekämpfungsmittel, Bakterizide, gegebenenfalls auch erst unmittelbar vor der Anwendung (Tankmix), zugesetzt werden. Diese Mittel können zu den erfindungsgemäßen Mitteln zugemischt werden, was üblicherweise im Ge- Wichtsverhältnis von 1:10 bis 10:1 erfolgt. Die Verbindungen I und II, bzw. die Mischungen oder die entsprechenden Formulierungen werden angewendet, indem man die Schadpilze, die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit einer f ungizid wirksa- men Menge der Mischung, bzw. der Verbindungen I und II bei getrennter Ausbringung, behandelt. Die Anwendung kann vor oder nach dem Befall durch die Schadpilze erfolgen.Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention, which is usually done in a weight ratio of 1:10 to 10: 1. The compounds I and II, or the mixtures or the corresponding formulations, are used in that the harmful fungi, the plants, seeds, soils, soils, areas, materials or spaces to be kept free from them are mixed with an amount of the mixture which is fungicidal, or of compounds I and II treated separately. The application can take place before or after the infestation by the harmful fungi.
Die fungizide Wirkung der Verbindung und der Mischungen lässt sich durch folgende Versuche zeigen:The fungicidal activity of the compound and the mixtures can be demonstrated by the following tests:
Die Wirkstoffe wurden getrennt oder gemeinsam als eine Stammlösung aufbereitet mit 0,25 Gew.-% Wirkstoff in Aceton oder DMSO. Dieser Lösung wurde 1 Gew.-% Emulga- tor Uniperol® EL (Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxy- lierter Alkylphenole) zugesetzt und entsprechend der gewünschten Konzentration mit Wasser verdünnt.The active ingredients were prepared separately or together as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO. 1% by weight of Uniperol® EL emulsifier (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
Anwendungsbeispiel - Wirksamkeit gegen die Braunfleckenkrankheit des Reises verursacht durch Cochliobolus miyabeanus bei protektiver BehandlungExample of use - effectiveness against brown spot disease of rice caused by Cochliobolus miyabeanus with protective treatment
Blätter von in Töpfen gewachsenen Reiskeimlingen der Sorte 'Tai-Nong 67" wurden mit wässriger Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht.. Am folgenden Tag wurden die Pflanzen mit einer wässrigen Sporensuspension von Cochliobolus miyabeanus inokuliert. Anschließend wurden die Ver- suchspflanzen in Klimakammern bei 22 - 24° C und 95 - 99 % relativer Luftfeuchtigkeit für 6 Tage aufgestellt. Dann wurde das Ausmaß der Befallsentwicklung auf den Blättern visuell ermittelt.Leaves of 'Tai-Nong 67' rice seedlings grown in pots were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. The following day, the plants were inoculated with an aqueous spore suspension of Cochliobolus miyabeanus. The test plants were then used set up in climatic chambers at 22 - 24 ° C and 95 - 99% relative humidity for 6 days, then the extent of the development of the infestation on the leaves was determined visually.
Die Auswertung erfolgt durch Feststellung der befallenen Blattflächen in Prozent. Diese Prozent-Werte wurden in Wirkungsgrade umgerechnet.The evaluation is carried out by determining the affected leaf areas in percent. These percentages were converted into efficiencies.
Der Wirkungsgrad (W) wird nach der Formel von Abbot wie folgt berechnet:Efficiency (W) is calculated using Abbot's formula as follows:
W = (1 - α/ß) Y00W = (1 - α / β) Y00
α entspricht dem Pilzbefall der behandelten Pflanzen in % und ß entspricht dem Pilzbefall der unbehandelten (Kontroll-) Pflanzen in % Bei einem Wirkungsgrad von 0 entspricht der Befall der behandelten Pflanzen demjenigen der unbehandelten Kontrollpflanzen; bei einem Wirkungsgrad von 100 weisen die behandelten Pflanzen keinen Befall auf. Die zu erwartenden Wirkungsgrade der Wirkstoffmischungen werden nach der Colby- Formel [R.S. Colby, Weeds 15, 20-22 (1967)] ermittelt und mit den beobachteten Wirkungsgraden verglichen.α corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in% With an efficiency of 0, the infection of the treated plants corresponds to that of the untreated control plants; with an efficiency of 100, the treated plants show no infection. The expected efficacies of the active ingredient mixtures are determined using the Colby formula [RS Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficiencies.
Colby Formel: E = x + y - x-y/100Colby formula: E = x + y - x-y / 100
E zu erwartender Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz der Mischung aus den Wirkstoffen A und B in den Konzentrationen a und b x der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs A in der Konzentration a y der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs B in der Konzentration bE expected efficiency, expressed in% of the untreated control, when using the mixture of active ingredients A and B in concentrations a and bx the efficiency, expressed in% of the untreated control, when using active ingredient A in concentration ay, the efficiency, expressed in% of the untreated control when using the active ingredient B in the concentration b
Tabelle A - EinzelwirkstoffeTable A - Individual substances
Tabelle B - erfindungsgemäße Mischungen Table B - mixtures according to the invention
*) berechneter Wirkungsgrad nach der Colby-Formel *) Efficiency calculated according to the Colby formula
Aus den Ergebnissen der Versuche geht hervor, dass die erfindungsgemäßen Mischungen in allen Mischungsverhältnissen deutlich wirksamer sind, als durch die Col- by-Formel vorausberechnet. The results of the experiments show that the mixtures according to the invention are significantly more effective in all mixing ratios than calculated in advance by the Colby formula.

Claims

Patentansprüche claims
1. Fungizide Mischungen zur Bekämpfung von pflanzenpathogenen Schadpilzen, enthaltend1. Containing fungicidal mixtures for controlling phytopathogenic harmful fungi
1 ) das Triazolopyrimidinderivat der Formel I,1) the triazolopyrimidine derivative of the formula I,
und 2) Thiophanate-Methyl der Formel II, and 2) thiophanate-methyl of the formula II,
in einer synergistisch wirksamen Menge. in a synergistically effective amount.
2. Fungizide Mischungen gemäß Anspruch 1, enthaltend die Verbindung der Formel I und die Verbindung der Formel II in einem Gewichts Verhältnis von 100:1 bis 1:100.2. Fungicidal mixtures according to claim 1, containing the compound of formula I and the compound of formula II in a weight ratio of 100: 1 to 1: 100.
3. Mittel, enthaltend einen flüssigen oder festen Trägerstoff und eine Mischung ge- maß einem der Ansprüche 1 oder 2.3. Agent containing a liquid or solid carrier and a mixture according to one of claims 1 or 2.
4. Verfahren zur Bekämpfung von pflanzenpathogenen Schadpilzen, dadurch gekennzeichnet, dass man die Pilze, deren Lebensraum oder die vor Pilzbefall zu schützenden Pflanzen, den Boden oder Saatgüter mit einer wirksamen Menge der Verbindung I und der Verbindung II gemäß Anspruch 1 behandelt.4. A method for controlling phytopathogenic harmful fungi, characterized in that the fungi, their habitat or the plants to be protected against fungal attack, the soil or seeds are treated with an effective amount of the compound I and the compound II according to claim 1.
5. Verfahren nach Anspruch 4, dadurch gekennzeichnet, dass man die Verbindungen I und II gemäß Anspruch 1 gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander ausbringt.5. The method according to claim 4, characterized in that the compounds I and II according to claim 1 simultaneously, jointly or separately, or in succession.
Verfahren nach Ansprüchen 4 oder 5, wobei reispathogene Schadpilze bekämpft werden. A method according to claims 4 or 5, wherein rice-pathogenic harmful fungi are controlled.
7. Verfahren nach einem der Ansprüche 4 bis 6, dadurch gekennzeichnet, dass man die Verbindungen I und II gemäß Anspruch 1 oder die Mischungen gemäß Ansprüchen 1 oder 2 in einer Menge von 5 g/ha b is 1000 g/ha aufwendet.7. The method according to any one of claims 4 to 6, characterized in that the compounds I and II according to claim 1 or the mixtures according to claims 1 or 2 in an amount of 5 g / ha to 1000 g / ha.
8. Verfahren nach einem der Ansprüche 4 bis 6, dadurch gekennzeichnet, dass man die Verbindungen I und II gemäß Anspruch 1 oder die Mischung gemäß Ansprüchen 1 oder 2 in einer Menge von 1 bis 1000 g/100 kg Saatgut anwendet.8. The method according to any one of claims 4 to 6, characterized in that the compounds I and II according to claim 1 or the mixture according to claims 1 or 2 in an amount of 1 to 1000 g / 100 kg of seed.
9. Saatgut, enthaltend die Mischung gemäß Ansprüchen 1 oder 2 in einer Menge von 1 bis 1000 g/100 kg.9. Seed containing the mixture according to claims 1 or 2 in an amount of 1 to 1000 g / 100 kg.
10. Verwendung der Verbindungen I und II gemäß Anspruch 1 zur Herstellung eines zur Bekämpfung von Schadpilzen geeigneten Mittels. 10. Use of the compounds I and II according to claim 1 for the preparation of an agent suitable for combating harmful fungi.
EP05736846A 2004-03-15 2005-03-14 Fungicidal mixtures made from a triazolopyrimidine derivative Withdrawn EP1727431A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004012752 2004-03-15
PCT/EP2005/002684 WO2005089542A2 (en) 2004-03-15 2005-03-14 Fungicidal mixtures made from a triazolopyrimidine derivative

Publications (1)

Publication Number Publication Date
EP1727431A2 true EP1727431A2 (en) 2006-12-06

Family

ID=34979577

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05736846A Withdrawn EP1727431A2 (en) 2004-03-15 2005-03-14 Fungicidal mixtures made from a triazolopyrimidine derivative

Country Status (16)

Country Link
US (1) US20080255158A1 (en)
EP (1) EP1727431A2 (en)
JP (1) JP2007529448A (en)
KR (1) KR20060131984A (en)
CN (1) CN1921760A (en)
AR (1) AR049371A1 (en)
AU (1) AU2005223999A1 (en)
BR (1) BRPI0508682A (en)
CA (1) CA2558006A1 (en)
CR (1) CR8580A (en)
EA (1) EA200601586A1 (en)
IL (1) IL177199A0 (en)
NO (1) NO20064168L (en)
TW (1) TW200608892A (en)
WO (1) WO2005089542A2 (en)
ZA (1) ZA200608555B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101180963B (en) * 2007-12-17 2012-04-18 东莞市瑞德丰生物科技有限公司 Composition containing Zhongshengmycin and thiophanate-methyl with synergism

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001297A (en) * 1968-06-18 1977-01-04 Nippon Soda Company Limited Thioureidobenzene preparations and uses thereof
US4940722A (en) * 1986-12-10 1990-07-10 Sumitomo Chemical Companmy, Limited Seed disinfectant composition
US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
JP3417995B2 (en) * 1994-04-12 2003-06-16 呉羽化学工業株式会社 Fungicide composition
TWI252231B (en) * 1997-04-14 2006-04-01 American Cyanamid Co Fungicidal trifluorophenyl-triazolopyrimidines
US6268371B1 (en) * 1998-09-10 2001-07-31 American Cyanamid Co. Fungicidal mixtures
EP0988790B1 (en) * 1998-09-25 2003-05-21 Basf Aktiengesellschaft Fungicidal mixtures

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005089542A2 *

Also Published As

Publication number Publication date
US20080255158A1 (en) 2008-10-16
IL177199A0 (en) 2006-12-10
AU2005223999A1 (en) 2005-09-29
KR20060131984A (en) 2006-12-20
ZA200608555B (en) 2008-06-25
TW200608892A (en) 2006-03-16
CA2558006A1 (en) 2005-09-29
AR049371A1 (en) 2006-07-26
WO2005089542A3 (en) 2005-12-22
EA200601586A1 (en) 2007-04-27
NO20064168L (en) 2006-09-26
CR8580A (en) 2007-02-05
WO2005089542A2 (en) 2005-09-29
BRPI0508682A (en) 2007-08-21
CN1921760A (en) 2007-02-28
JP2007529448A (en) 2007-10-25

Similar Documents

Publication Publication Date Title
WO2004105490A1 (en) Fungicidal mixtures for controlling rice pathogens
WO2005110088A2 (en) Triazolopyrimidine derivative-based fungicide mixtures
EP1720409A1 (en) Fungicidal mixtures
EP1740049B1 (en) Fungicidal mixtures
WO2004103075A1 (en) Fungicidal mixtures
WO2005067716A1 (en) Fungicidal mixtures
EP1708573A1 (en) Fungicide mixtures
WO2005032257A1 (en) Fungicidal mixtures for fighting against rice pathogens
WO2005112643A1 (en) Fungicide mixtures
EP1727431A2 (en) Fungicidal mixtures made from a triazolopyrimidine derivative
WO2005060752A1 (en) Fungicidal mixtures for controlling rice pathogens
WO2005039295A1 (en) Fungicidal mixtures
WO2005104849A1 (en) Fungicidal mixtures
EP1737298A1 (en) Fungicide mixtures based on a triazolopyrimidine derivative
EP1694125A1 (en) Fungicidal mixtures
WO2005041666A1 (en) Fungicidal mixtures
WO2005067714A1 (en) Fungicidal mixtures in order to combat harmful fungi
WO2005082146A1 (en) Fungicide mixtures for controlling rice pathogens
WO2005070208A1 (en) Fungicidal mixtures for the control of rice pathogens
EP1684586A1 (en) Fungicidal mixtures for the prevention of rice pathogens
EP1746890A1 (en) Fungicide triazolopyrimidine derivative-based mixtures
EP1740048A1 (en) Fungicidal mixtures
WO2005089554A1 (en) Fungicidal mixtures based on triazolopyrimidine derivatives
EP1819228A2 (en) Fungicide mixtures based on a triazolopyrimidine derivative
WO2005089553A1 (en) Fungicidal mixtures for controlling rice pathogens

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: 20061016

AK Designated contracting states

Kind code of ref document: A2

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

AX Request for extension of the european patent

Extension state: LV

RAX Requested extension states of the european patent have changed

Extension state: LV

Payment date: 20061016

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BASF SE

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RIC1 Information provided on ipc code assigned before grant

Ipc: A01P 3/00 20060101ALI20081010BHEP

Ipc: A01N 47/34 20060101ALI20081010BHEP

Ipc: A01N 43/90 20060101AFI20081010BHEP

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: 20080901