EP1809105A2 - Melanges fongicides bases sur des derives de triazolopyrimidine - Google Patents

Melanges fongicides bases sur des derives de triazolopyrimidine

Info

Publication number
EP1809105A2
EP1809105A2 EP05747553A EP05747553A EP1809105A2 EP 1809105 A2 EP1809105 A2 EP 1809105A2 EP 05747553 A EP05747553 A EP 05747553A EP 05747553 A EP05747553 A EP 05747553A EP 1809105 A2 EP1809105 A2 EP 1809105A2
Authority
EP
European Patent Office
Prior art keywords
compound
formula
compounds
mixtures
fungicidal mixtures
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Withdrawn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
EP05747553A
Other languages
German (de)
English (en)
Inventor
Jordi Tormo I Blasco
Thomas Grote
Maria Scherer
Reinhard Stierl
Siegfried Strathmann
Ulrich Schöfl
Joachim Rheinheimer
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 EP1809105A2 publication Critical patent/EP1809105A2/fr
Withdrawn legal-status Critical Current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
    • 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 fungicidal mixtures containing as active components
  • variables have the following meaning: AO or N; BN or a direct bond; GC or N; R 1 CC 4 alkyl; R 2 CC 4 alkoxy; and R 3 halogen;
  • the invention also relates to a method for controlling harmful fungi with mixtures of the compound I with compounds II and the use of the compound I with compounds II for the production of such mixtures and agents which contain these mixtures.
  • 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 compounds II or the simultaneous joint or separate use of the compound I and compounds II are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. They can be used in plant protection as leaf, pickling and soil fungicides.
  • the compound I and compounds 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.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals with 1 to 4 carbon atoms, for example CC 4 alkyl such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl;
  • R 1 is n-propyl or n-butyl, in particular n-propyl.
  • Formula II particularly represents compounds of formulas 11.1, II.2 and II.3:
  • the compound of the formula 11.1, in which R 1 is n-propyl, R 2 is n-propoxy and R 3 is iodine, is known by the common name “procinazide” (compound 11.1-1). Mixtures of the compound of the formula I and procinazide, are a preferred embodiment of the invention. Mixtures containing the compound of the formula I and a compound of the formula II.2 are also a preferred embodiment of the invention.
  • a further preferred embodiment of the invention relates to mixtures of the compound I and one of the following compounds of the formula 11.3:
  • Fungicides selected from the following group are particularly suitable as further active ingredients in the above sense: Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, 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 iprodione, myclozolin, procymidone, vinclozolin,
  • Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamat, Thiram, Ziram, Zineb, • Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamidite, dazonometone , Famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronil, nuarimol, penthiopyrad, picobenzamide, probenazol, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thiophylzoline, thiadlazoline, thiflanidiline, thiflanidyl amine
  • Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate,
  • Nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitrophthal-isopropyl,
  • Phenylpyrroles such as fenpiclonil or fludioxonil, sulfur,
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamid, cymoxanil, diclomezin, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, namimzone, fluimazosi, fluazi, fluazi Fosetyl aluminum, iprovalicarb, hexachlorobenzene, mandipropamide, metrafenone, pencycuron, propamocarb, phosphorous acid, phthalide, toloclofos-methyl, quintozene, zoxamide,
  • strobilurins such as azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, cresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, • sulfenoic acid derivatives such as captafol, captan, dichlofluanfluanid, folpet, tolpet, tolpet
  • 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.
  • Mixtures of the compounds I and II with a component III are preferred. Mixtures of compounds I and II are particularly preferred.
  • the compound I and the compound II are usually used in a weight ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:20, in particular 10: 1 to 1:10.
  • components III and, if appropriate, IV are mixed in a ratio of 20: 1 to 1:20 to compound I.
  • the application rates of the mixtures according to the invention are 5 g / ha to 1000 g / ha, preferably 50 to 900 g / ha, in particular 50 to 750 g / ha.
  • the application rates for the compound I are accordingly generally from 1 to 1000 g / ha, preferably from 10 to 900 g / ha, in particular from 20 to 750 g / ha.
  • the application rates for the compound II are generally from 1 to 1000 g / ha, preferably from 10 to 900 g / ha, in particular from 40 to 750 g / ha.
  • application rates of mixture of 1 to 1000 g / 100 kg of seed preferably 1 to 750 g / 100 kg, in particular 5 to 500 g / 100 kg, are generally used.
  • the method for controlling harmful fungi is carried out by the separate or joint application of the compound I and the compound II or the mixtures of the compound I and the compound II by spraying or dusting the seeds, the plants or the soil before or after the plants are sown or before or after emergence of the plants.
  • 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, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
  • solvents / auxiliaries Water, aromatic solvents (e.g. Solvesso products, xylene), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol, pentanol, benzyl alcohol), ketones (e.g.
  • cyclohexanone gamma-butryolactone
  • pyrrolidones NMP, NOP
  • acetates Glycol diacetate
  • glycols dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used, carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Emulsifiers such
  • 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 for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate .
  • Ammonium phosphate, ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • 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
  • Water-dispersible and water-soluble granules 50 parts by weight of the active ingredients become fine with the addition of dispersing and wetting agents ground 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.
  • 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, oldispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the purposes of use; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, old dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents 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 are usually added to the agents according to the invention 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, areas, materials or spaces to be kept free from them are mixed with a fungicidally effective amount of the mixture or the compounds I and II when applied 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 emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
  • emulsifier Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • Leaves of "Kanzler" wheat seedlings grown in pots were sprayed to runoff point with an aqueous suspension in the active compound concentration given below.
  • the suspension or emulsion was prepared as described above. 5 days after application of the active ingredient, the plants were treated with spores of wheat powdery mildew ⁇ Erysiphe [syn. Blumeria] graminis forma specialis. tritici) pollinated.
  • the test plants were then grown in the greenhouse at temperatures between 20 Wheat powdery mildew (Erysiphe [syn. Blumeria] graminis forma specialis. Tritici) pollinated.
  • the test plants were then placed in a greenhouse at temperatures between 20 and 24 ° C and 60 to 90% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area.
  • ⁇ corresponds to the fungal attack of the treated plants in% and 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.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (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)

Abstract

L'invention concerne des mélanges fongicides qui contiennent comme composants actifs: 1) un dérivé de triazolopyrimidine correspondant à la formule (I); et 2) au moins un composé correspondant à la formule (II), dans laquelle A représente O ou N; B représente N ou une liaison directe, G représente C ou N; R1 représente alkyle; R2 représente alcoxy et R3 représente halogène. Lesdits mélanges contiennent lesdits composants en des quantités leur conférant une efficacité synergique. L'invention concerne également un procédé de lutte contre des champignons nuisibles faisant appel à des mélanges du composé (I) avec des composés (II), l'utilisation du composé (I) avec les composés (II) pour la production de tels mélanges, ainsi que des agents contenant ces mélanges.
EP05747553A 2004-05-13 2005-05-11 Melanges fongicides bases sur des derives de triazolopyrimidine Withdrawn EP1809105A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102004024201 2004-05-13
DE102005011582 2005-03-10
PCT/EP2005/005068 WO2005110088A2 (fr) 2004-05-13 2005-05-11 Melanges fongicides

Publications (1)

Publication Number Publication Date
EP1809105A2 true EP1809105A2 (fr) 2007-07-25

Family

ID=35394625

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05747553A Withdrawn EP1809105A2 (fr) 2004-05-13 2005-05-11 Melanges fongicides bases sur des derives de triazolopyrimidine

Country Status (12)

Country Link
US (1) US20070197557A1 (fr)
EP (1) EP1809105A2 (fr)
JP (1) JP2007537191A (fr)
AR (1) AR048956A1 (fr)
AU (1) AU2005244420A1 (fr)
BR (1) BRPI0509784A (fr)
CA (1) CA2560219A1 (fr)
EA (1) EA200602046A1 (fr)
IL (1) IL178017A0 (fr)
NO (1) NO20065043L (fr)
TW (1) TW200612828A (fr)
WO (1) WO2005110088A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CL2007003256A1 (es) * 2006-11-15 2008-07-25 Du Pont Mezcla fungicida que comprende al menos tres compuestos diferentes; composicion fungicida que comprende dicha mezcla; y metodo para controlar una enfermedad en plantas causada por el patogeno fungico vegetal que comprende aplicar una cantidad de la m
US20100190645A1 (en) * 2007-02-02 2010-07-29 Anne Suty-Heinze Synergistic fungicidal active compound combinations comprising formononetin
US9126044B2 (en) * 2010-04-15 2015-09-08 Cardiac Pacemakers, Inc. Autonomic modulation using transient response with intermittent neural stimulation

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA9711323B (en) * 1997-01-30 1999-06-17 I E Du Pont De Nemours And Com Fungicidal mixtures
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
ATE240648T1 (de) * 1998-09-25 2003-06-15 Basf Ag Fungizide mischungen
CN1238348C (zh) * 2001-05-21 2006-01-25 巴斯福股份公司 用作杀真菌剂的噁嗪(硫)酮化合物
FR2828196A1 (fr) * 2001-08-03 2003-02-07 Aventis Cropscience Sa Derives de chromone a action fongicide, procede de preparation et application dans le domaine de l'agriculture
US6627985B2 (en) * 2001-12-05 2003-09-30 Arbor Company Llp Reconfigurable processor module comprising hybrid stacked integrated circuit die elements
WO2003103393A1 (fr) * 2002-06-11 2003-12-18 E.I. Du Pont De Nemours And Company Melanges de pyrimidinones et de composes dinitrophenoliques utiles pour lutter contre l'oidium

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005110088A2 *

Also Published As

Publication number Publication date
WO2005110088A2 (fr) 2005-11-24
CA2560219A1 (fr) 2005-11-24
BRPI0509784A (pt) 2007-10-23
EA200602046A1 (ru) 2007-06-29
WO2005110088A3 (fr) 2006-02-16
IL178017A0 (en) 2006-12-31
US20070197557A1 (en) 2007-08-23
TW200612828A (en) 2006-05-01
AU2005244420A1 (en) 2005-11-24
JP2007537191A (ja) 2007-12-20
AR048956A1 (es) 2006-06-14
NO20065043L (no) 2006-12-08

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