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
• R 2 is hydrogen or one of the groups mentioned for R 1 ;
• R 1 and R 2 can also together form a straight-chain or branched C 3 -C 8 alkylene chain;
• L fluorine, chlorine or bromine; m 2 or 3;
• the invention also relates to a process for combating harmful fungi with mixtures of compounds of the formula I and inhibitors II and / or III by using the mixtures according to the invention and the use of the compounds I with inhibitors II and / or III for the production of such mixtures and agents which contain these mixtures.
• Inhibitors II and / or III are generally known as growth regulators in agriculture. They relate in particular to active ingredients from the groups: acylcyclohexanedione compounds of the formula Ha wherein
• R represents hydrogen, CC 8 alkyl, CrC 8 alkylthioalkyl or unsubstituted or substituted by one to three groups R a phenyl and R a halogen, nitro, cyano, amino, C 1 -C 8 alkyl, CC 4 haloalkyl, dC 8 -alkoxy or C- ⁇ -C haloalkoxy may be substituted.
• Triazolyls as inhibitors of cytochrome P-450-dependent monooxygenases, which block the metabolism of gibberellins as the main effect, such as paclobutrazole (llb.1) or uniconazole (llb.2); quaternary ammonium compounds (llc) which inhibit early reactions in gibberellin biosynthesis, in particular chlormequat chloride (llc.1), mepiquatch chloride (llc.2) and mepiquat pentaborate (llc.3); and inhibitors of auxin transport (III), in particular 2- ⁇ 1- [4- (3,5-difluorophenyI) semicarbazono] ethyl ⁇ nicotinic acid, common name diflufenzopyr (III.1).
• the aim of the invention was therefore to find active ingredient combinations which have an improved activity against harmful fungi and reduce the likelihood of tolerance or resistance formation against fungicidal active ingredients.
• Prohexadione is usually used in the form of an alkali or alkaline earth metal salt, in particular as a calcium salt: Prohexadione-Ca (Ila.1): EP-A 123001; Trinexapac, is usually used as an ester or salt; especially as ethyl ester: trinexapac-ethyl (Ila.2): EP-A 126713; Paclobutrazole (llb.1): Proc. Br. Crop Prot. Conf. - Weeds, 1982, Vol. 1, p. 3; Uniconazole (llb.2): Plant Cell Physiol., 1984, Vol. 25, p.
• Chlormequat is usually used in the form of a salt, such as chloride: chlormequatch chloride (IIc.1): US 3 156 554; DE 11 99 048; Mepiquat, is usually used in the form of a salt, such as chloride: mepiquat chloride (IIc.2) or pentaborate: mepiquat pentaborate (IIc.3): US 3,905,798; DE 22 07 575.
• Diflufenzopyr (III.1) is often used in the form of a salt, such as the sodium salt: Proc. Br. Crop Prot. Conf. - Weeds, 1999, Vol. 1, p. 35.
• Acylcyclohexanediones of the formula Ia are particularly suitable as growth regulators since, in addition to their morphoregulatory effect, they can also protect crop plants against biotic and abiotic stressors [ see: EP-A 123 001, page 27, lines 20 and 21 (for prohexadiones and related substances) or for trinexapac-ethyl and related compounds in EP-A 126713]. From Bazzi et al. (European Journal of Horological Science 68; p.108-114; p.115-122) resistance induction by the compounds mentioned against certain pathogens is known.
• diflufenzopyr of the formula III.1 not only optimizes the efficiency of fungicides, but also brings about increased yield in useful plants (WO 01/43544).
• Fungicidal mixtures of 5-chloro-triazolopyrimidines with fungicidal active ingredients are generally known from EP-A 988 790 and US 6268 371.
• D denotes a straight-chain or branched C 3 -C 8 alkylene chain, in particular a branched C 5 alkylene chain, such as 3-methyl-pentylene.
• Y represents hydrogen or methyl.
• the compound 1-1,5-chloro-7- (4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2.4 ] triazolo [1, 5-a] pyrimidine particularly preferred.
• the mixtures of the compound I and the inhibitors II and / or IM or the simultaneous joint or separate use of the compound I and the inhibitors II and / or III are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. They can be used in plant protection as leaf, pickling and soil fungicides.
• the compound I and the inhibitors II and / or III can be applied simultaneously together or separately or in succession, with the application of the inhibitors II and / or III preferably taking place first when the application is separate.
• 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,
• Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamat, Thiram, Ziram, Zineb,
• Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidon, fenarimol, isoprothiolan, pentazolidolid, prozolidolid, prozolid Pyrifenox, pyroquilon, qui- noxyfen, silthiofam, thiabendazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazol, triforins,
• 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
• 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 IV or two fungicides IV and V are added to the compounds I and II / III.
• Mixtures of the compounds I and II / III with a component IV are preferred. Mixtures of the compounds I and II or III are particularly preferred.
• Mixtures of a compound I with an inhibitor II or III are usually used. Under certain circumstances, however, mixtures with a compound with two or more inhibitors II and / or III can be advantageous.
• the compound I and the inhibitors 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 compound I and the inhibitors III, in particular the compound 111.1 are usually used in a weight ratio of 1000: 1 to 1: 1, preferably 200: 1 to 20: 1.
• components IV and optionally V 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 inhibitors II are generally from 1 to 1000 g / ha, preferably from 10 to 900 g / ha, in particular from 40 to 750 g / ha.
• the application rates for the inhibitors III, in particular the compound III.1, are accordingly generally from 0.01 to 50 g / ha, preferably 0.1 to 10 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 in arable crops is carried out by the separate or joint application of the compound I and the inhibitors II and / or III or the mixtures of the compound I and the inhibitors II and / or III by spraying or dusting the seeds , the plants or the soil before or after sowing the plants or before or after emergence of the plants.
• treatment is preferably carried out before or during the annual growth phase.
• the mixtures according to the invention, or the compounds I and II / III, 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 (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, gamma Butryolactone
• 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
• 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 ner purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
• formulations are: 1. Products for dilution in water
• 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 added with the addition of dispersing and wetting agents. grind like silica gel in a rotor-strator mill. 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 agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
• the active substance 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 / III, 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 from them are mixed with a fungicidally effective amount of the mixture or Compounds I and II / III treated separately.
• the application can take place before or after the infestation by the harmful fungi.
• 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 apples were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. 12 days later, the treated plants were inoculated with an aqueous spore suspension of Venturia inaequalis. The apples were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 20 days in a greenhouse at temperatures between 20 and 24 ° C. The extent of the development of the infestation on the top of the leaf was then determined visually.
• Efficiency (W) is calculated using Abbot's formula as follows:
• W (1 - ⁇ / ß) - 100 ⁇ 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.
• E x + y - xy / 100 E 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 the active ingredient A in the concentration ay the efficiency, expressed in% of the untreated control, when using the active ingredient B in the concentration b
• Leaves of potted vines were sprayed to runoff point with an aqueous suspension in the active ingredient concentration given below.
• the plants were placed in the greenhouse for 9 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous suspension of zoospores from Plasmopara viticola.
• the vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually.

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• 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)
• Pretreatment Of Seeds And Plants (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)

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