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: A oxathiin or 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur or oxygen atom, where A can be substituted by one or two identical or different substituents R.
• R is hydrogen, CrC 4 alkyl, CrC 4 alkylcarbonyl or a group A bonded via carbonyl;
• R a , R b independently of one another halogen, cyano, CC 4 alkyl, C -C 4 haloalkyl, CrCe alkoxycarbonyl, CrC 4 alkoxy, CC 4 haloalkoxy, C 1 -C 4 alkylthio, CC 4 alkylcarbonyl, Formyl, -CC 4 alkylene or C 2 -C 4 alkenylene, which connects two adjacent carbon atoms; m 0, 1, 2, 3, 4 or 5, where R a can be the same or different if n is greater than 1, n 0, 1 or 2; where R b may be the same or different when n is 2; in a synerg
• the invention relates to a method for controlling harmful fungi with mixtures of the compound I with a compound 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 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, pickling and soil fungicides. 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.
• Ascomycetes 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
• they are suitable for combating harmful fungi from the Oomycetes class. They can also be used in material protection (e.g. wood protection), for example against Paecilomyces variotii.
• material protection e.g. wood protection
• 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.
• 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, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1-dimethylethyl;
• Haloalkyl straight-chain or branched alkyl groups with 1 or 2 carbon atoms (as mentioned above), in which case the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above: in particular CrC 2 haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, tri- chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro 2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentaflu
• 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur or oxygen atom
• 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members can, e.g.
• Alkylene divalent unbranched chains from 1 to 4 CH 2 groups, for example CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 ;
• Formula II particularly represents compounds in which the index n denotes 1 or 2, preferably 1.
• the biphenyl amides correspond to the formula IIA:
• R a is preferably selected from the following groups: halogen, such as fluorine, chlorine, bromine; cyano; CC 4 alkyl, such as methyl; -C-C 4 haloalkyl, such as trifluoromethyl; CC - Alkoxy such as methoxy; CC 4 haloalkoxy such as trifluoromethoxy; CC 4 alkylthio, such as methylthio.
• the biphenylamides correspond to the formula IIB:
• the biphenylamides correspond to the formula IIC:
• the biphenylamides correspond to the formula HD:
• 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,
• Copper fungicides such as Bordeaux broth, copper oxychloride, copper hydroxide, copper oxide, (basic) copper sulfate, copper oxychloride sulfate,
• 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, dichlofluanid, folpet, tolylfluanid,
• 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 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.
• 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 compound II are generally from 1 to 1000 g / ha, preferably from 10 to 900 g / ha, in particular from 40 to 500 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. On the run of the plants.
• the mixtures according to the invention, or the compounds I and II, can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
• the application form 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 and auxiliaries The following are essentially considered as solvents / auxiliaries:
• 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 glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
• 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 waste liquors and methyl cellulose.
• natural stone powder e.g. kaolins, clays, talc, chalk
• 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 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 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.
• 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
• 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 with the addition of dispersants and wetting agents Crushed water or an organic solvent in a stirred ball mill to a fine active ingredient suspension. Dilution in water results in a stable suspension of the active ingredient.
• Water-dispersible and water-soluble granules 50 parts by weight of the active ingredients are finely ground with the addition of dispersing and wetting agents and produced as water-dispersible or water-soluble granules by means of technical equipment (e.g. extrusion, spray tower, fluidized bed). Dilution in water results in a stable dispersion or solution of the active ingredient.
• 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 the.
• 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 consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
• 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, surfaces, materials or spaces to be kept free of them are mixed with a fungicidally effective amount of the mixture or Compounds I and II treated separately.
• the application can take place before or after the infestation by the harmful fungi.
• the active ingredients were prepared separately as a stock solution with 25 mg of active ingredient which was mixed with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in a volume ratio of solvent emulsifier from 99 to 1 ad 10 ml was filled. Then ad 100 ml was made up with water. The active substances or mixtures were diluted or mixed with water in accordance with the stated concentration.
• Example of use - Effectiveness against barley mesh stain caused by Pyrenophora teres with 1 day protective application
• ⁇ 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.

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• 2005
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