EP1903868A1 - Fungicidal mixtures made from 1-methylpyrazol-4-ylcarboxanilides - Google Patents

Fungicidal mixtures made from 1-methylpyrazol-4-ylcarboxanilides

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Publication number
EP1903868A1
EP1903868A1 EP06777561A EP06777561A EP1903868A1 EP 1903868 A1 EP1903868 A1 EP 1903868A1 EP 06777561 A EP06777561 A EP 06777561A EP 06777561 A EP06777561 A EP 06777561A EP 1903868 A1 EP1903868 A1 EP 1903868A1
Authority
EP
European Patent Office
Prior art keywords
methyl
carboxylic acid
amide
chloro
pyrazole
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Withdrawn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
EP06777561A
Other languages
German (de)
French (fr)
Inventor
Jochen Dietz
Markus Gewehr
Siegfried Strathmann
Reinhard Stierl
Frank Werner
Maria Scherer
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
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP06777561A priority Critical patent/EP1903868A1/en
Publication of EP1903868A1 publication Critical patent/EP1903868A1/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to fungicidal mixtures containing as active components 1) at least one i-methylpyrazol-4-ylcarbonklaanilid of formula I.
  • R 1 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl and R 2 is hydrogen or halogen
  • Azoles selected from bichertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triaza dimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamide, benomyl, carbendazim, thiadendazole, fuberidazole, ethaboxam, etridiazole and hymex
  • strobilurins selected from azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, (2-chloro-5- [1- (3-methylbenzyl-oxyimino methyl (ethyl) benzyl) carbamate, (2-chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester and 2- (ortho- (2,5-) Dimethylphenyl-oxymethylene) phenyl) -3-methoxy-acrylic acid methyl ester;
  • Carboxylic acid amides selected from carboxin, benalaxyl, boscalid, fenhexamide, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxine, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro-N- (2-cyanophenyl ) -isothiazole-5-carboxamide, dimethomorph, flumorph, fl uidover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet,
  • R 4 is methyl or ethyl
  • Z is N or CH
  • Antibiotics Kasugamycin, Streptomycin, Polyoxin, Validamycin A,
  • Nitrophenyl derivatives binapacryl, dinocap, dinobutone, sulfur-containing heterocyclyl compounds: dithianone, isoprothiolane,
  • Organometallic compounds fentin salts such as fentin acetate,
  • Inorganic active ingredients Bordeaux broth, copper acetate, copper hydroxide,
  • the invention relates to a method for controlling harmful fungi with mixtures of at least one compound I and at least one of the active compounds II, the use of the compound (s) I with active ingredients) II for the preparation of such mixtures and agents and seeds containing these mixtures.
  • EP-A 589301 discloses 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (2'-fluoromethylbiphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-1H pyrazole-4-carboxylic acid N- (2'-fluoromethylbiphenyl-2-yl) -amide and 1,3-dimethyl-1-methyl-1H-pyrazole-4-carboxylic acid N- (2'-fluoromethylbiphenyl-2 -yl) -amide.
  • EP-A 545099, WO 99/09013, WO 01/42223 and JP 09/132567 disclose substituted pyrazolylcarboxylic acid biphenylamides which are monosubstituted on the phenyl ring.
  • Those compounds I in which X is sulfur can be prepared, for example, by sulfurization of the corresponding compounds I in which X is oxygen (cf., for example, D. Petrova & K. Jakobcic, Croat. Chem. Acta 48, 49 (1976 ) and WO 01/42223).
  • WO 05/34628 describes mixtures of pyrazol-4-ylcarboxylic acid anilides of the type of the compounds I with a multiplicity of different mixing partners.
  • component 2 active compounds II, their preparation and their
  • Action against harmful fungi is well known (see, for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.
  • alkyl also includes octyl, decyl, tetradecyl and
  • Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE-A 11 64 152);
  • Cycloheximide 4 - ⁇ (2R) -2 - [(1S, 3S, 5S) -3,5-dimethyl-2-oxocyclohexyl] -2-hydroxyethyl ⁇ piperidine-2,6-dione [CAS RN 66-81 -9]; Griseofulvin, 7-chloro-2 ', 4,6-triethoxy-6'-methylpiro [benzofuran-2 (3H), 1'-cyclohex-2'-ene] -3,4'-dione [CAS RN 126-07 -8th];
  • Ipconazole 2 - [(4-chlorophenyl) methyl] -5- (1-methylethyl) -1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (EP-A 267,778);
  • Penconazole 1- [2- (2,4-dichlorophenyl) pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12.
  • Prothioconazole 2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro- [1,2,4] triazole-3-thione (WO 96/16048) ; Simeconazole, ⁇ - (4-fluorophenyl) - ⁇ - [(trimethylsilyl) methyl] -1H-1,2,4-triazole-1-ethanol
  • Tetraconazole 1 - [2- (2,4-dichlorophenyl) -3- (1,1,2,2-tetrafluoroethoxy) propyl] -1H-1, 2,4-triazole (EP-A 234 242);
  • Metam methyldithiocarbamic acid (US 2,791,605); Metiram, zinc ammonium ethylenebis (dithiocarbamate) (US 3,248,400);
  • Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);
  • Zineb zinc ethylenebis (dithiocarbamate) (US 2,457,674);
  • Cyazofamide 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide (CAS RN 120116-88-3];
  • Flutolanil ⁇ , ⁇ , ⁇ -trifluoro-3'-isopropoxy-o-toluanilide (JP 1104514); Furametpyr, 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88-3 ];
  • Isoprothiolane, diisopropyl 1, 3-dithiolan-2-ylidene malonate Proc. Insectic. Fungic. Conf.
  • 1-propylpentyl is (US 2,526,660);
  • Nitrothal isopropyl, diisopropyl 5-nitroisophthalate (Proc. Br. Insectic., Fungic, Conf., 7: 2, 673 (1973));
  • Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
  • Cymoxanil 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (US 3,957,847); Diclomethine, 6- (3,5-dichlorophenyl-p-tolyl) pyridazine-3 (2H) -one (US 4,052,395);
  • Penthiopyrad (RS) -N- [2- (1, 3-dimethylbutyl) -3-thienyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (JP 10/130268); Propamocarb, 3- (dimethylamino) propylcarbamic acid isopropyl ester (DE-A 1567 169);
  • Azoxystrobin 2- ⁇ 2- [6- (2-cyano-1-vinyl-penta-1,3-dienyloxy) -pyrimidin-4-yloxy] -phenyl ⁇ -
  • Picoxystrobin 3-methoxy-2- [2- (6-trifluoromethylpyridin-2-yloxyn-ethyl) -phenyl] -acrylic acid methyl ester (EP-A 278 595); Pyraclostrobin, N- ⁇ 2- [1- (4-chlorophenyl) -1H-pyrazol-3-yloxymethyl] phenyl ⁇ (N-methoxy) carbamic acid, ethyl ester (WO 96/01256);
  • Trifloxystrobin (E) -methoxyimino- ⁇ (E) - ⁇ - [1- ( ⁇ , ⁇ , ⁇ -trifluoro-n-tolyl) -ethylidene-amino-oxy] -o-tolyl ⁇ -acetic acid methyl ester (EP-A 460 575);
  • the present invention mixtures were the object of an improved effect against harmful fungi, especially for certain indications show with reduced total amount of active substances.
  • the mixtures of active ingredients I and II defined above were found. It has also been found that it is possible to combat harmful fungi more effectively in the simultaneous, combined or separate use of at least one compound I and of at least one of the active compounds II, or the compound (s) I and at least one of the active compounds II with the individual compounds alone (synergistic mixtures).
  • the compounds I can be used as synergists for a variety of different fungicidal agents.
  • the fungicidal activity is increased to a superadditive extent.
  • the compounds I can be present in various crystal modifications, which may differ in their biological activity.
  • halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;
  • C 1 -C 4 -alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl, preferably methyl or ethyl;
  • Ci-C 4 haloalkyl is a partially or completely halogenated Ci-C 4 - alkyl group, wherein the / the halogen atom (s) is especially fluorine, chlorine and / or bromine / are eg chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, 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, pentafluoroethy
  • the 1-methylpyrazol-4-ylcarbonklaanilide of formula I are known from WO 99/09013, JP 09/132567 and the earlier application PCT / EP2006 / 062219 or can be prepared in the manner described therein.
  • the compounds I in which X is sulfur can be prepared, for example, by sulfurization of the corresponding compounds I in which X is oxygen (cf., for example, D. Petrova & K. Jakobcic, Croat. Chem. Acta 48, 49 (1976 ) and WO 01/42223).
  • R 1 is C 1 -C 4 -haloalkyl, preferably halomethyl, in particular CHF 2 or CF 3 .
  • R 2 is hydrogen, fluorine or chlorine, in particular hydrogen.
  • mixtures of a compound of formula I with at least one active ingredient selected from the group of D) heterocyclic compounds are also preferred.
  • mixtures of a compound of formula I with at least one active ingredient selected from the group of E) carbamates are also preferred.
  • mixtures of a compound of formula I with at least one active ingredient selected from the group of F) other fungicides are also preferred.
  • A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole , Prothioconazole, Tria
  • active compound selected from the group consisting of a) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon,
  • active substance selected from the group of A) azoles selected from epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim.
  • active compound selected from the group of F fungicides selected from dithianone, fentin salts such as fentin acetate, fosetyl, fosetyl aluminum, phosphorous acid and their salts, chlorothalonil, dichlofluanide , Thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, cymox
  • Other fungicides selected from phosphorous acid and its salts, chlorothalonil and metrafenone.
  • the mixtures of compound (s) I and at least one of the active compounds II, or the simultaneous joint or separate use of at least one compound I with at least one of the active compounds II, are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. They can also be used for seed treatment.
  • Alternaria species on vegetables, rapeseed, sugar beets and fruits and rice e.g. A. solani or A. alternata on potatoes and tomatoes, - Aphanomyces species on sugar beet and vegetables, Ascochyta species on cereals and vegetables,
  • Bipolaris and Drechslera species on corn, cereals, rice and turf eg D. maydis on corn, Blumeria graminis (powdery mildew) on cereals,
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines
  • Cercospora species on corn, soybeans, rice and sugar beets - Cochliobolus species on maize, cereals, rice, e.g. Cochliobolus sativus on cereals,
  • Drechslera species Pyrenophora species on corn, cereals, rice and turf, e.g. D. teres to barley or D. tritici-repentis to wheat, - Esca to grapevine, caused by Phaeoacremonium chlamydosporium, Ph.
  • Fusarium and Verticillium species on various plants e.g. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, e.g. Tomatoes,
  • Gibberella species on cereals and rice e.g., Gibberella fujikuroi on rice
  • Mycosphaerella species on cereals, bananas and peanuts e.g. M. graminicola on wheat or M. fijiesis on bananas,
  • Peronospora species on cabbage and bulbous plants e.g. P. brassicae on cabbage or P. destructor on onion,
  • Phytophthora species on various plants e.g. P. capsici on paprika, - Plasmopara viticola on vines,
  • Pseudoperonospora on various plants e.g. P. cubensis on cucumber or
  • Puccinia species on various plants e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals or P. asparagi on asparagus,
  • Pyricularia grisea on lawn and cereals - Pythium spp. on grass, rice, maize, cotton, rapeseed, sunflower, sugar beets, vegetables and other plants, eg P. ultiumum on various plants, P. aphanidermatum on lawn, Rhizoctonia species on cotton, rice, potatoes, turf, corn, oilseed rape, sugar beets, vegetables and on various plants, eg R. solani on beets and various plants,
  • Ustilago species on cereals, corn and sugar beet e.g. U. maydis on corn
  • Venturia species (scab) on apples and pears e.g. V. inaequalis to apple.
  • the mixtures according to the invention are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriela spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophlum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderm spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • the compound (s) I with at least one of the active ingredients II can be applied simultaneously, namely jointly or separately, or in succession, the sequence in the case of separate application generally having no effect on the control result.
  • the pure active ingredients I to II are preferably used, to which other active substances can be added against harmful fungi or against other pests such as insects, spider animals or nematodes or else herbicidal or growth-regulating active substances or fertilizers.
  • Such mixtures of three active ingredients consist, for example, of a compound of the formula I, in particular 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide or 3 -Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide, an azole from group A), in particular epoxiconazole, metconazole, triticonazole or fluquinconazole, and an insecticide, in particular fipronil and neonicotinoids such as acetamiprid, clothiani din, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam.
  • an insecticide in particular fipronil and neonicotinoids such as acetamiprid, clothiani din, di
  • mixtures of at least one compound I and at least one active ingredient II are used.
  • mixtures of at least one compound I with two or, if desired, several active components can also offer particular advantages.
  • Suitable further active components in the above sense are, in particular, the aforementioned active compounds II and in particular the above-mentioned preferred active compounds II.
  • the compound (s) I and active compound (II) 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 further active components are mixed in a ratio of from 20: 1 to 1:20 to give compound I.
  • the application rates of the mixtures according to the invention at 5 g / ha to 2000 g / ha, preferably 20 to 1500 g / ha, in particular 50 to 1000 g /Ha.
  • the application rates for the compound (s) I are accordingly generally 1 to 1000 g / ha, preferably 10 to 900 g / ha, in particular 20 to 750 g / ha.
  • the application rates for the active compound II are accordingly generally from 1 to 2000 g / ha, preferably from 10 to 1500 g / ha, in particular from 40 to 1000 g / ha.
  • application rates of mixture of 1 to 1000 g per 100 kg of seed, preferably 1 to 750 g per 100 kg, in particular 5 to 500 g per 100 kg of seed are generally used.
  • the method for controlling harmful fungi is carried out by the separate or combined application of compound (s) I and active ingredients) II, or a mixture of compound (s) I and at least one of the active compounds II, by spraying or dusting the seeds, the plants or soils before or after sowing the plants or before or after emergence of the plants.
  • the fungicidal mixtures according to the invention, or the compound (s) I and at least one of the active compounds II, can be converted into the customary formulations are, for example, solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application form depends on the respective purpose; It should in any case ensure the finest possible and uniform distribution of the mixture according to the invention.
  • the formulations are prepared in a manner known per se, for example by stretching the active compounds with solvents and / or excipients, if desired using emulsifiers and dispersants.
  • Solvents / auxiliaries which are suitable are essentially: - water, aromatic solvents (for example Solvesso ® products, xylene), paraffins
  • solvent mixtures can also be used.
  • alcohols eg, methanol, butanol, pentanol, benzyl alcohol
  • ketones eg, cyclohexanone, gamma-butyrolactone
  • pyrrolidones N-methylpyrrolidone, N-octylpyrrolidone
  • acetates glycols, dimethyl fatty acid amides , Fatty acids and fatty acid esters.
  • solvent mixtures can also be used.
  • Excipients such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • ground natural minerals e.g., kaolins, clays, talc, chalk
  • ground synthetic minerals e.g., fumed silica, silicates
  • Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
  • the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as
  • Granules e.g. Coating, impregnation and homogeneous granules can be prepared by binding the active ingredients to at least one solid carrier.
  • Solid carriers are e.g. Mineral soils 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 cereal flour, tree bark, wood and nutshell flour, Ce I Iu loose powder and other solid carriers.
  • the formulations generally contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compound (s) I and at least one of the active compounds II or of the mixture of compound (I) I with at least one of the active ingredients II.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • formulations are: 1. Products for dilution in water
  • a mixture according to the invention 20 parts by weight of a mixture according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersing agent, e.g. Polyvinylpyrrolidone, dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight.
  • Emulsifiable Concentrates 15 parts by weight of a mixture according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 15% by weight.
  • a mixture according to the invention 25 parts by weight of a mixture according to the invention are dissolved in 35 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate in each case 5% by weight. Parts) solved.
  • This mixture is added by means of an emulsifying machine (eg Ultraturrax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • a mixture according to the invention 20 parts by weight of a mixture according to the invention are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine Wirkstoffsuspensi- on. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • 50 parts by weight of a mixture according to the invention are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of industrial equipment (for example 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.
  • the formulation has an active ingredient content of 50% by weight.
  • 75 parts by weight of a mixture according to the invention are ground with the addition of 25 parts by weight of dispersants and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of a mixture according to the invention are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
  • 10 parts by weight of a mixture according to the invention are in 90 parts by weight of a dissolved organic solvent such as xylene. This gives a product for direct application with an active ingredient content of 10 wt .-%.
  • the active compounds can be used 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, scattering agents, granules by spraying, misting, dusting, scattering or pouring.
  • the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active substances.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil 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, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. 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 (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume
  • wetting agents to give the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • adjuvants in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ® ; Alcohol alkoxylates, eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®; EO-PO block polymers, eg. B. Pluro- nic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
  • organically modified polysiloxanes eg Break Thru S 240 ®
  • Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO-PO block polymers eg. B. Pluro
  • the compounds I and II, or the mixtures or the corresponding formulations are applied by the harmful fungi, their habitat or the treated plants, seeds, soils, areas, materials or spaces with a fungicidally effective amount of the mixture, or the compounds I and II with separate application treated.
  • the application can be made before or after the attack by the harmful fungi.
  • the active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or dimethyl sulfoxide and the emulsifier Uniperol ® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent- Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the active ingredient concentration given below.
  • Uniperol ® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the active ingredients epoxiconazole, triticonazole and pyraclostrobin were used as a commercially available ready-made formulation and diluted with water to the stated active substance concentrations.
  • the efficiency (W) is calculated according to the formula of Abbot as follows:
  • ⁇ corresponds to the fungal infestation of the treated plants in% and ⁇ corresponds to the fungal infestation of the untreated (control) plants in%
  • the infestation of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants have no infestation.
  • E x + y - x ° y / 100 expected efficiency, expressed as% of untreated control, when using the mixture of Active Agents A and B at concentrations a and b; the efficiency, expressed in% of untreated control, when using active substance A at concentration a; the efficiency expressed as% of untreated control when using active substance B in concentration b.
  • Paprika seedlings of the cultivar "Neusiedler Ideal Elite" were sprayed to drip point after 2-3 leaves had developed well, and the next day the treated plants were treated with a spore suspension of Botrytis cinerea, the 1 x 7 x 10 6 spores / ml in a 2% aqueous biomalt solution, and the test plants were placed in a climatic chamber at 22 to 24 ° C, in the dark and at high humidity Scrolls can be determined visually in%.
  • the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in dimethylsulfoxide.
  • the active ingredient triticonazole was used as a commercial formulation and diluted with water to the specified concentration.
  • the stock solution was pipetted into a microtiter plate (MTP) and diluted with an aqueous fungus nutrient medium based on pea juice to the stated active substance concentration. This was followed by the addition of an aqueous zoospore suspension of Phytophthora infestans.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. Using an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
  • the measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.

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Abstract

The invention relates to fungicidal mixtures containing the following active components 1) at least one 1-methylpyrazol-4-ylcarboxanilide (I), where X = O or S, R<SUP>1</SUP> = C<SUB>1</SUB>-C<SUB>4</SUB> alkyl or C<SUB>1</SUB>-C<SUB>4</SUB> haloalkyl and R<SUP>2</SUP> = H or halogen and 2) at least one agent (II), selected from the agent groups A) to F): A) azoles, B) strobilurines, C) carboxamides, D) heterocyclic compounds, E) carbamates, F) other fungicides in synergistically effective amounts, method for prevention of fungal pests with mixtures of at least one compound (I) and at least one agent (II), the use of compound(s) (I) with agents (II) for the production of such mixtures and agents and seed containing said mixtures.

Description

Fungizide Mischungen auf der Basis von i-Methylpyrazol-4-ylcarbonsäureanilidenFungicidal mixtures based on i-methylpyrazol-4-ylcarbonsäureaniliden
Beschreibungdescription
Die vorliegende Erfindung betrifft fungizide Mischungen, enthaltend als aktive Komponenten 1) mindestens ein i-Methylpyrazol-4-ylcarbonsäureanilid der Formel IThe present invention relates to fungicidal mixtures containing as active components 1) at least one i-methylpyrazol-4-ylcarbonsäureanilid of formula I.
in der X für Sauerstoff oder Schwefel, R1 für Ci-C4-AIkVl oder Ci-C4-Halogenalkyl und R2 für Wasserstoff oder Halogen stehen, und in which X is oxygen or sulfur, R 1 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl and R 2 is hydrogen or halogen, and
2) mindestens einen Wirkstoff II, ausgewählt aus den Wirkstoffgruppen A) bis F):2) at least one active ingredient II selected from the active ingredient groups A) to F):
A) Azole, ausgewählt aus Bitertanol, Bromuconazol, Cyproconazol, Difenocon- azol, Diniconazol, Enilconazol, Epoxiconazol, Fluquinconazol, Fenbuconazol, Flusilazol, Flutriafol, Hexaconazol, Imibenconazol, Ipconazol, Metconazol, Myclobutanil, Penconazol, Propiconazol, Prothioconazol, Simeconazol, Tria- dimefon, Triadimenol, Tebuconazol, Tetraconazol, Triticonazol, Prochloraz, Pefurazoate, Imazalil, Triflumizol, Cyazofamid, Benomyl, Carbendazim, Thia- bendazol, Fuberidazol, Ethaboxam, Etridiazol und Hymexazol;A) Azoles selected from bichertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triaza dimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamide, benomyl, carbendazim, thiadendazole, fuberidazole, ethaboxam, etridiazole and hymexazole;
B) Strobilurine, ausgewählt aus Azoxystrobin, Dimoxystrobin, Enestroburin, FIu- oxastrobin, Kresoxim-methyl, Methominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin, Enestroburin, (2-Chlor-5-[1-(3-methyl-benzyl- oxyimino)-ethyl]-benzyl)-carbaminsäuremethylester, (2-Chlor-5-[1-(6-methyl- pyridin-2-ylmethoxyimino)-ethyl]-benzyl)-carbaminsäuremethylester und 2-(ortho-(2,5-Dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylsäure- methylester;B) strobilurins selected from azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, (2-chloro-5- [1- (3-methylbenzyl-oxyimino methyl (ethyl) benzyl) carbamate, (2-chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester and 2- (ortho- (2,5-) Dimethylphenyl-oxymethylene) phenyl) -3-methoxy-acrylic acid methyl ester;
C) Carbonsäureamide, ausgewählt aus Carboxin, Benalaxyl, Boscalid, Fenhex- amid, Flutolanil, Furametpyr, Mepronil, Metalaxyl, Mefenoxam, Ofurace, Oxadixyl, Oxycarboxin, Penthiopyrad, Thifluzamid, Tiadinil, 3,4-Dichlor-N-(2- cyanophenyl)-isothiazol-5-carbonsäureamid, Dimethomorph, Flumorph, FIu- metover, Fluopicolid (Picobenzamid), Zoxamid, Carpropamid, Diclocymet,C) Carboxylic acid amides selected from carboxin, benalaxyl, boscalid, fenhexamide, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxine, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro-N- (2-cyanophenyl ) -isothiazole-5-carboxamide, dimethomorph, flumorph, fl uidover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet,
Mandipropamid, N-(2-(4-[3-(4-Chlor-phenyl)-prop-2-ynyloxy]-3-methoxy- phenyl)-ethyl)-2-methansulfonylamino-3-methyl-butyramid, N-(2-(4-[3-(4- Chlor-phenyl)-prop-2-ynyloxy]-3-methoxy-phenyl)-ethyl)-2-ethansulfonyl- amino-3-methyl-butyrannid, 3-(4-Chlor-phenyl)-3-(2-isopropoxy-carbonylamino- 3-methyl-butyrylamino)-propionsäure-nnethylester, Verbindungen der FormelMandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino-3-methylbutyramide, N- (2- [4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxy-phenyl) -ethyl) -2-ethanesulfonyl methyl 3-methyl-butyranedione, 3- (4-chloro-phenyl) -3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino) -propionic acid, compounds of the formula
in der R4 Methyl oder Ethyl bedeutet, in which R 4 is methyl or ethyl,
4-Difluormethyl-2-methyl-thiazol-5-carbonsäure-N-(4'-brom-biphenyl-2-yl)- amid, 4-Difluormethyl-2-methyl-thiazol-5-carbonsäure-N-(4'-trifluormethyl- biphenyl-2-yl)-amid, 4-Difluormethyl-2-methyl-thiazol-5-carbonsäure-N-(4'- chlor-3'-fluor-biphenyl-2-yl)-amid, 3-Difluormethyl-1-methyl-pyrazol-4- carbonsäure-N-(3',4'-dichlor-4-fluor-biphenyl-2-yl)-amid und 3,4-Dichlor- isothiazol-5-carbonsäure-N-(2-cyano-phenyl)-amid;4-Difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4 ' -trifluoromethyl-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-chloro-3'-fluorobiphenyl-2-yl) -amide, 3 Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide and 3,4-dichloro-isothiazole-5-carboxylic acid-N- (2-cyano-phenyl) -amide;
D) Heterocyclische Verbindungen, ausgewählt aus Fluazinam, Pyrifenox, Bupirimat, Cyprodinil, Fenarimol, Ferimzon, Mepanipyrim, Nuarimol, Pyri- methanil, Triforin, Fenpiclonil, Fludioxonil, Aldimorph, Dodemorph, Fenpropi- morph, Tridemorph, Fenpropidin, Iprodion, Procymidon, Vinclozolin, Famoxadon, Fenamidon, Octhilinon, Probenazol, 5-Chlor-7-(4-methyl- piperidin-1 -yl)-6-(2,4,6-trifluor-phenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin, Anilazin, Diclomezin, Pyroquilon, Proquinazid, Tricyclazol, die Verbindung derD) Heterocyclic compounds selected from fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforin, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin , Famoxadone, fenamidone, octhilinone, probenazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [ 1, 5-a] pyrimidine, anilazine, diclomethine, pyroquilon, proquinazide, tricyclazole, the compound of
Formel IV (2-ButoFormula IV (2-buto
Acibenzolar-S-methyl, Captafol, Captan, Dazomet, Folpet, Fenoxanil, Quin- oxyfen und 3-(3-Brom-6-fluor-2-methyl-indol-1-sulfonyl)-[1 ,2,4]triazol-1-sulfon- säuredimethylamid der Formel VAcibenzolar-S-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen and 3- (3-bromo-6-fluoro-2-methyl-indole-1-sulfonyl) - [1, 2,4] triazole 1-sulfonic acid dimethylamide of the formula V
E) Carbamate, ausgewählt aus Mancozeb, Maneb, Metam, Metiram, Ferbam, Propineb, Thiram, Zineb, Ziram, Diethofencarb, Iprovalicarb, Flubenthiavali- carb, Propamocarb, N-(1 -(1 -(4-cyanophenyl)ethanesulfonyl)-but-2-yl)-carb- aminsäure-(4-fluorphenyl)ester, 3-(4-Chlor-phenyl)-3-(2-isopropoxy-carbonyl- amino-3-methyl-butyrylamino)-propansäuremethylester der Formel VI und Carbamatoxim-ether der Formel VIIE) Carbamates selected from Mancozeb, Maneb, Metam, Metiram, Ferbam, Propineb, Thiram, Zineb, Ziram, Diethofencarb, Iprovalicarb, Flubenthiavali- carb, Propamocarb, N- (1- (1 - (4-cyanophenyl) ethanesulfonyl) - But-2-yl) -carbamic acid (4-fluorophenyl) ester, 3- (4-chloro-phenyl) -3- (2-isopropoxy-carbonyl-amino-3-methyl-butyrylamino) -propanoic acid of the formula VI and carbamato oxime ether of the formula VII
in der Z für N oder CH steht; Z is N or CH;
F) Sonstige Fungizide, ausgewählt ausF) Other fungicides selected from
Guanidin, Dodin, Iminoctadin, Guazatin,Guanidine, dodin, iminoctadine, guazatine,
Antibiotika: Kasugamycin, Streptomycin, Polyoxin, Validamycin A,Antibiotics: Kasugamycin, Streptomycin, Polyoxin, Validamycin A,
Nitrophenylderivate: Binapacryl, Dinocap, Dinobuton, Schwefelhaltige Heterocyclylverbindungen: Dithianon, Isoprothiolan,Nitrophenyl derivatives: binapacryl, dinocap, dinobutone, sulfur-containing heterocyclyl compounds: dithianone, isoprothiolane,
Organometallverbindungen: Fentin-Salzen wie Fentin-acetat,Organometallic compounds: fentin salts such as fentin acetate,
Organophosphorverbindungen: Edifenphos, Iprobenfos, Fosetyl,Organophosphorus Compounds: Edifenphos, Iprobenfos, Fosetyl,
Fosetyl-Aluminium, Phosphorige Säure und ihre Salze, Pyrazophos, Tolclofos- methyl, Organochlorverbindungen: Chlorthalonil, Dichlofluanid, Flusulfamid, Hexa- chlorbenzol, Phthalid, Pencycuron, Quintozen, Thiophanat-Methyl, Tolylflua- nid,Fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl, organochlorine compounds: chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluoride,
Anorganische Wirkstoffe: Bordeaux Brühe, Kupferacetat, Kupferhydroxid,Inorganic active ingredients: Bordeaux broth, copper acetate, copper hydroxide,
Kupferoxychlorid, basisches Kupfersulfat, Schwefel, Sonstige: Cyflufenamid, Cymoxanil, Dimethirimol, Ethirimol,Copper oxychloride, basic copper sulphate, sulfur, others: cyflufenamid, cymoxanil, dimethirimol, ethirimol,
Furalaxyl, Metrafenon und Spiroxamin;Furalaxyl, Metrafenone and Spiroxamine;
in einer synergistisch wirksamen Menge.in a synergistically effective amount.
Außerdem betrifft die Erfindung ein Verfahren zur Bekämpfung von Schadpilzen mit Mischungen aus mindestens einer Verbindung I und mindestens einem der Wirkstoffe II, die Verwendung der Verbindung(en) I mit Wirkstoffen) Il zur Herstellung derartiger Mischungen sowie Mittel und Saatgut enthaltend diese Mischungen.In addition, the invention relates to a method for controlling harmful fungi with mixtures of at least one compound I and at least one of the active compounds II, the use of the compound (s) I with active ingredients) II for the preparation of such mixtures and agents and seeds containing these mixtures.
Aus der EP-A 589301 sind z.B. 1-Methyl-3-trifluormethyl-1 H-pyrazol-4-carbonsäure-N- (2'-fluormethylbiphenyl-2-yl)-amid, 3-Difluormethyl-1 -methyl-1 H-pyrazol-4-carbonsäure- N-(2'-fluormethylbiphenyl-2-yl)-amid und 1 ,3-Dimethyl-1 -methyl-1 H-pyrazol-4- carbonsäure-N-(2'-fluormethylbiphenyl-2-yl)-amid bekannt. Aus der EP-A 545099, WO 99/09013, WO 01/42223 und der JP 09/132567 sind substituierte Pyrazolylcarbonsäurebiphenylamide bekannt, die am Phenylring monosubstitu- iert sind.For example, EP-A 589301 discloses 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (2'-fluoromethylbiphenyl-2-yl) -amide, 3-difluoromethyl-1-methyl-1H pyrazole-4-carboxylic acid N- (2'-fluoromethylbiphenyl-2-yl) -amide and 1,3-dimethyl-1-methyl-1H-pyrazole-4-carboxylic acid N- (2'-fluoromethylbiphenyl-2 -yl) -amide. EP-A 545099, WO 99/09013, WO 01/42223 and JP 09/132567 disclose substituted pyrazolylcarboxylic acid biphenylamides which are monosubstituted on the phenyl ring.
Diejenigen Verbindungen I, bei denen X für Schwefel steht, sind beispielsweise durch Schwefelung der entsprechenden Verbindungen I, bei denen X für Sauerstoff steht, herstellbar (vgl. z.B. D. Petrova & K. Jakobcic, Croat. Chem. Acta 48, 49 (1976) sowie die WO 01/42223).Those compounds I in which X is sulfur can be prepared, for example, by sulfurization of the corresponding compounds I in which X is oxygen (cf., for example, D. Petrova & K. Jakobcic, Croat. Chem. Acta 48, 49 (1976 ) and WO 01/42223).
In der WO 05/34628 werden Mischungen aus Pyrazol-4-ylcarbonsäureaniliden vom Typ der Verbindungen I mit einer Vielzahl von verschiedenen Mischungspartnern beschrieben.WO 05/34628 describes mixtures of pyrazol-4-ylcarboxylic acid anilides of the type of the compounds I with a multiplicity of different mixing partners.
Die beschriebenen Mischungen können jedoch, insbesondere bei niedrigen Aufwand- mengen, nur bedingt befriedigen.However, the described mixtures can only partially satisfy, especially at low application rates.
Die voranstehend als Komponente 2) genannten Wirkstoffe II, ihre Herstellung und ihreThe above-mentioned as component 2) active compounds II, their preparation and their
Wirkung gegen Schadpilze sind allgemein bekannt (vgl. z.B. http://www.hclrss.demon.co.uk/index.html); sie sind kommerziell erhältlich.Action against harmful fungi is well known (see, for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.
Benalaxyl, Methyl N-(phenylacetyl)-N-(2,6-xylyl)-DL-alaninat (DE 29 03 612);Benalaxyl, methyl N- (phenylacetyl) -N- (2,6-xylyl) -DL-alaninate (DE 29 03 612);
Metalaxyl, Methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninat (GB 15 00 581);Metalaxyl, methyl N- (methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate (GB 15 00 581);
Ofurace, (RS)-α-(2-Chlor-N-2,6-xylylacetamido)-γ-butyrolacton [CAS RN 58810-48-3];Ofurace, (RS) -α- (2-chloro-N-2,6-xylylacetamido) -γ-butyrolactone [CAS RN 58810-48-3];
Oxadixyl, N-(2,6-dimethylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)acetamid (GB 20 58 059);Oxadixyl, N- (2,6-dimethylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide (GB 20 58 059);
Aldimorph, "4-Alkyl-2,5(oder 2,6)-dimethylmorpholin", enthaltend 65-75% 2,6-Dimethyl- morpholin und 25-35% 2,5-Dimethylmorpholin, enthaltend mehr als 85% 4-Dodecyl-Aldimorph, "4-alkyl-2,5 (or 2,6) -dimethylmorpholine" containing 65-75% 2,6-dimethylmorpholine and 25-35% 2,5-dimethylmorpholine containing more than 85% 4- dodecyl
2,5(oder 2,6)-Dimethylmorpholin, wobei "alkyl" auch Octyl, Decyl, Tetradecyl und2,5 (or 2,6) -dimethylmorpholine, wherein "alkyl" also includes octyl, decyl, tetradecyl and
Hexadecyl mit einem cis/trans Verhältnis von 1 :1 einschließt [CAS RN 91315-15-0]; Dodin, 1-Dodecylguanidinium acetate (Plant Dis. Rep. 41, S.1029 (1957));Hexadecyl having a cis / trans ratio of 1: 1 [CAS RN 91315-15-0]; Dodin, 1-dodecylguanidinium acetate (Plant Dis. Rep. 41, p.1029 (1957));
Dodemorph, 4-Cyclododecyl-2,6-dimethylmorpholin (DE-A 1198125);Dodemorph, 4-cyclododecyl-2,6-dimethylmorpholine (DE-A 1198125);
Fenpropimorph, (RS)-cis-4-[3-(4-tert-Butylphenyl)-2-methylpropyl]-2,6-dimethyl- morpholin (DE-A 27 52 096);Fenpropimorph, (RS) -cis-4- [3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (DE-A 27 52 096);
Fenpropidin, (RS)-I -[3-(4-tert-Butylphenyl)-2-methylpropyl]piperidin (DE-A 27 52 096); Guazatin, Mischung der Reaktionsprodukte, erhalten aus der Amidierung von technischem lminodi(octamethylen)diamin, enthaltend verschiedene Guanidine und PoIy- amine [CAS RN 108173-90-6];Fenpropidin, (RS) -I - [3- (4-tert-butylphenyl) -2-methylpropyl] piperidine (DE-A 27 52 096); Guazatine, mixture of the reaction products obtained from the amidation of technical lminodi (octamethylene) diamine containing various guanidines and polyamines [CAS RN 108173-90-6];
Iminoctadin, 1 ,1'-lminodi(octamethylen)diguanidin (Congr. Plant Pathol., 1., S. 27Iminoctadin, 1, 1'-lminodi (octamethylene) diguanidine (Congr. Plant Pathol., 1, p
(1968); Spiroxamin, (8-Tert-butyl-1 ,4-dioxaspiro[4.5]dec-2-yl)diethylamin (EP-A 281 842);(1968); Spiroxamine, (8-tert-butyl-1,4-dioxaspiro [4.5] dec-2-yl) diethylamine (EP-A 281 842);
Tridemorph, 2,6-Dimethyl-4-tridecylmorpholin (DE-A 11 64 152);Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE-A 11 64 152);
Pyrimethanil, 4,6-Dimethylpyrimidin-2-yl-phenylamin (DD-A 151 404); Mepanipyrim, (4-Methyl-6-prop-1-inyl-pyrimidin-2-yl)-phenylamin (EP-A 224 339);Pyrimethanil, 4,6-dimethylpyrimidin-2-yl-phenylamine (DD-A 151 404); Mepanipyrim, (4-methyl-6-prop-1-ynyl-pyrimidin-2-yl) -phenylamine (EP-A 224 339);
Cyprodinil, (4-Cyclopropyl-6-methylpyrimidin-2-yl)phenylamin (EP-A 310 550);Cyprodinil, (4-cyclopropyl-6-methylpyrimidin-2-yl) -phenylamine (EP-A 310550);
Cycloheximid, 4-{(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}pi- peridin-2,6-dion [CAS RN 66-81-9]; Griseofulvin, 7-Chlor-2',4,6-trinnethoxy-6'-nnethylspiro[benzofuran-2(3H), 1 '-cyclohex-2'- ene]-3,4'-dion [CAS RN 126-07-8];Cycloheximide, 4 - {(2R) -2 - [(1S, 3S, 5S) -3,5-dimethyl-2-oxocyclohexyl] -2-hydroxyethyl} piperidine-2,6-dione [CAS RN 66-81 -9]; Griseofulvin, 7-chloro-2 ', 4,6-triethoxy-6'-methylpiro [benzofuran-2 (3H), 1'-cyclohex-2'-ene] -3,4'-dione [CAS RN 126-07 -8th];
Kasugamycin, 3-O-[2-Amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-α-D- arabino-hexopyranosyl]-D-chiro-inositol [CAS RN 6980-18-3];Kasugamycin, 3-O- [2-Amino-4 - [(carboxymiminomethyl) amino] -2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl] -D-chiro-inositol [CAS RN 6980-18 -3];
Natamycin, (8E, 14E, 16E, 18E,20E)-(1 R,3S,5R,7R, 12R,22R,24S,25R,26S)-22-(3-Ami- no-3,6-dideoxy-ß-D-mannopyranosyloxy)-1 ,3,26-trihydroxy-12-methyl-10-oxo-6, 11 ,28- trioxatricyclo[22.3.1.05φctacosa-8,14,16,18,20-pentaene-25-carbonsäure [CAS RNNatamycin, (8E, 14E, 16E, 18E, 20E) - (1R, 3S, 5R, 7R, 12R, 22R, 24S, 25R, 26S) -22- (3-amino-3,6-dideoxy- β-D-mannopyranosyloxy) -1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo [22.3.1.0 5 φctacosa-8,14,16,18,20-pentaene-25 -carboxylic acid [CAS RN
7681-93-8];7681-93-8];
Polyoxin, 5-(2-Amino-5-O-carbamoyl-2-deoxy-L-xylonamido)-1 -(5-carboxy-1 ,2,3,4- tetrahydro-2,4-dioxopyrimidin-1-yl)-1 ,5-dideoxy-ß-D-allofuranuronsäure [CAS RN 22976-86-9];Polyoxine, 5- (2-Amino-5-O-carbamoyl-2-deoxy-L-xylonamido) -1- (5-carboxy-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-1-yl ) -1, 5-dideoxy-β-D-allofuranuronic acid [CAS RN 22976-86-9];
Streptomycin, 1 ,1'-{1-L-(1,3,5/2,4,6)-4-[5-Deoxy-2-O-(2-deoxy-2-nnethylannino-α-L- glucopyranosyl)-3-C-formyl-α-L-lyxofuranosyloxy]-2,5,6-trihydroxycyclohex-1 ,3- ylene}diguanidin (J. Am. Chem. Soc. 69, S.1234 (1947));Streptomycin, 1, 1 '- {1-L- (1,3,5 / 2,4,6) -4- [5-deoxy-2-O- (2-deoxy-2-n-ethylannino-α-L) glucopyranosyl) -3-C-formyl-α-L-xyxofuranosyloxy] -2,5,6-trihydroxycyclohex-1, 3-ylene} diguanidine (J. Am. Chem. Soc. 69, p.1234 (1947));
Bitertanol, ß-([1 , 1 '-Biphenyl]-4-yloxy)-α-(1 , 1 -dimethylethyl)-1 H-1 ,2,4-triazol-1 -ethanol (DE-A 23 24 020);Bitertanol, β - ([1,1'-biphenyl] -4-yloxy) -α- (1,1-dimethylethyl) -1H-1,2,4-triazole-1-ethanol (DE-A 23 24 020 );
Bromuconazol, 1 -[[4-Brom-2-(2,4-dichlorphenyl)tetrahydro-2-furanyl]methyl]-1 H-1 ,2,4- triazol (Proc. 1990 Br. Crop. Prot. Conf. - Pests Dis., Bd. 1, S. 459);Bromuconazole, 1 - [[4-bromo-2- (2,4-dichlorophenyl) tetrahydro-2-furanyl] methyl] -1H-1, 2,4-triazole (Proc. 1990 Br. Crop. Prot. Conf. - Pests Dis., Vol. 1, p. 459);
Cyproconazol, 2-(4-Chlorphenyl)-3-cyclopropyl-1 -[1 ,2,4]triazol-1 -ylbutan-2-olCyproconazole, 2- (4-chlorophenyl) -3-cyclopropyl-1 - [1, 2,4] triazole-1-yl-butan-2-ol
(US 4,664,696); Difenoconazol, 1-{2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl-[1 ,3]dioxolan-2- ylmethyl}-1 H-[1 ,2,4]triazol (GB-A 2 098 607);(US 4,664,696); Difenoconazole, 1- {2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl- [1,3-dioxolan-2-ylmethyl} -1 H- [1,2,4] triazole ( GB-A 2 098 607);
Diniconazol, (ßE)-ß-[(2,4-Dichlorphenyl)methylen]-α-(1 , 1 -dimethylethyl)-1 H-1 ,2,4- triazol-1 -ethanol (Noyaku Kagaku, 1983, Bd. 8, S. 575);Diniconazole, (βE) -β - [(2,4-dichlorophenyl) methylene] -α- (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol (Noyaku Kagaku, 1983, Vol 8, p. 575);
Enilconazol (Imazalil), 1-[2-(2,4-Dichlorphenyl)-2-(2-propenyloxy)ethyl]-1 H-imidazol (Fruits 28, S. 545, 1973);Enilconazole (imazalil), 1- [2- (2,4-dichlorophenyl) -2- (2-propenyloxy) ethyl] -1H-imidazole (Fruits 28, p. 545, 1973);
Epoxiconazol, (2RS,3SR)-1 -[3-(2-Chlorphenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1 H-Epoxiconazole, (2RS, 3SR) -1 - [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl] -1 H-
1 ,2,4-triazol (EP-A 196 038);1, 2,4-triazole (EP-A 196 038);
Fenbuconazol, α-[2-(4-Chlorphenyl)ethyl]-α-phenyl-1 H-1 ,2,4-triazole-1-propannitrilFenbuconazole, α- [2- (4-chlorophenyl) ethyl] -α-phenyl-1H-1, 2,4-triazole-1-propanenitrile
(Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., Bd. 1 , S. 33); Fluquinconazol, 3-(2,4-Dichlorphenyl)-6-fluor-2-[1 ,2,4]-triazol-1-yl-3H-quinazolin-4-on(Proc., 1988 Br. Crop Prot. Conf. - Pests Dis., Vol. 1, p. 33); Fluquinconazole, 3- (2,4-dichlorophenyl) -6-fluoro-2- [1, 2,4] -triazol-1-yl-3H-quinazolin-4-one
(Proc. Br. Crop Prot. Conf.-Pests Dis., 5-3, 411 (1992));(Proc. Br. Crop Prot. Conf.-Pests Dis., 5-3, 411 (1992));
Flusilazol, 1-{[Bis-(4-fluorophenyl)methylsilanyl]methyl}-1 H-[1 ,2,4]triazol (Proc. Br. CropFlusilazole, 1 - {[bis (4-fluorophenyl) methylsilanyl] methyl} -1 H- [1,2,4] triazole (Proc. Br. Crop
Prot. Conf.-Pests Dis., Bd. 1, S. 413 (1984));Prot. Conf.-Pests Dis., Vol. 1, p. 413 (1984));
Flutriafol, α-(2-Fluorphenyl)-α-(4-fluorphenyl)-1 H-1 , 2,4-triazol-1 -ethanol (EP-A 15 756); Hexaconazol, 2-(2,4-Dichlorphenyl)-1 -[1 ,2,4]triazol-1 -yl-hexan-2-ol (CAS RNFlutriafol, α- (2-fluorophenyl) -α- (4-fluorophenyl) -1H-1, 2,4-triazole-1-ethanol (EP-A 15,756); Hexaconazole, 2- (2,4-dichlorophenyl) -1 - [1, 2,4] triazole-1-yl-hexan-2-ol (CAS RN
79983-71-4); Ipconazol, 2-[(4-Chlorphenyl)methyl]-5-(1-methylethyl)-1-(1 H-1 ,2,4-triazol-1-yl- methyl)cyclopentanol (EP-A 267 778);79983-71-4); Ipconazole, 2 - [(4-chlorophenyl) methyl] -5- (1-methylethyl) -1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (EP-A 267,778);
Metconazol, 5-(4-Chlorbenzyl)-2,2-dimethyl-1 -[1 ,2,4]triazol-1 -ylmethylcyclopentanolMetconazole, 5- (4-chlorobenzyl) -2,2-dimethyl-1 - [1, 2,4] triazole-1-ylmethylcyclopentanol
(GB 857 383); Myclobutanil, 2-(4-Chlorphenyl)-2-[1 ,2,4]triazol-1-ylnnethyl-pentannitril (CAS RN 88671-(GB 857,383); Myclobutanil, 2- (4-chlorophenyl) -2- [1,2,4] triazol-1-ylmethylpentanenitrile (CAS RN 88671-
89-0);89-0);
Penconazol, 1-[2-(2,4-Dichlorphenyl)pentyl]-1 H-[1 ,2,4]triazol (Pesticide Manual, 12.Penconazole, 1- [2- (2,4-dichlorophenyl) pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12.
Auflage 2000, S. 712);Edition 2000, p. 712);
Propiconazol, 1 -[[2-(2,4-Dichlorphenyl)-4-propyl-1 ,3-dioxolan-2-yl]methyl]-1 H-1 ,2,4- triazol (BE 835 579);Propiconazole, 1 - [[2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-yl] methyl] -1H-1, 2,4-triazole (BE 835,579);
Prochloraz, lmidazol-1-carbonsäure-propyl-[2-(2,4,6-trichlorphenoxy)-ethyl]-annidProchlorazole, imidazole-1-carboxylic acid-propyl- [2- (2,4,6-trichlorophenoxy) -ethyl] -annide
(US 3,991 ,071);(US 3,991,071);
Prothioconazol, 2-[2-(1-Chlorcyclopropyl)-3-(2-chlorphenyl)-2-hydroxypropyl]-2,4- dihydro-[1 ,2,4]triazol-3-thion (WO 96/16048); Simeconazol, α-(4-Fluorophenyl)-α-[(trimethylsilyl)methyl]-1 H-1 ,2,4-triazol-1 -ethanolProthioconazole, 2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro- [1,2,4] triazole-3-thione (WO 96/16048) ; Simeconazole, α- (4-fluorophenyl) -α - [(trimethylsilyl) methyl] -1H-1,2,4-triazole-1-ethanol
[CAS RN 149508-90-7];[CAS RN 149508-90-7];
Tebuconazol, 1 -(4-Chlorphenyl)-4,4-dimethyl-3-[1 ,2,4]triazol-1 -ylmethyl-pentan-3-olTebuconazole, 1- (4-chlorophenyl) -4,4-dimethyl-3- [1,2,4] triazole-1-ylmethylpentan-3-ol
(EP-A 40 345);(EP-A 40 345);
Tetraconazol, 1 -[2-(2,4-Dichlorphenyl)-3-(1 , 1 ,2,2-tetrafluorethoxy)propyl]-1 H-1 ,2,4- triazol (EP-A 234 242);Tetraconazole, 1 - [2- (2,4-dichlorophenyl) -3- (1,1,2,2-tetrafluoroethoxy) propyl] -1H-1, 2,4-triazole (EP-A 234 242);
Triadimefon, 1 -(4-Chlorphenoxy)-3,3-dimethyl-1 -(1 H-1 ,2,4-triazol-1 -yl)-2-butanon (BETriadimefon, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1, 2,4-triazol-1-yl) -2-butanone (BE
793 867);793 867);
Triadimenol, ß-(4-Chlorphenoxy)-α-(1 ,1-dimethylethyl)-1 H-1 ,2,4-triazol-1 -ethanol (DE-ATriadimenol, β- (4-chlorophenoxy) -α- (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol (DE-A
23 24 010); Triflumizol, (4-Chlor-2-trifluormethylphenyl)-(2-propoxy-1 -[1 ,2,4]triazol-1 -yl-ethyliden)- amin (JP-A 79/119 462);23 24 010); Triflumizole, (4-chloro-2-trifluoromethylphenyl) - (2-propoxy-1 - [1, 2,4] triazole-1-yl-ethylidene) -amine (JP-A 79/119 462);
Triticonazol, (5E)-5-[(4-Chlorphenyl)methylen]-2,2-dimethyl-1 -(1 H-1 ,2,4-triazol-1 -yl- methyl)cyclopentanol (FR 26 41 277);Triticonazole, (5E) -5 - [(4-chlorophenyl) methylene] -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (FR 26 41 277) ;
Iprodion, 3-(3,5-Dichlorphenyl)-2,4-dioxo-imidazolidin-1-carbonsäureisopropylamid (GB 13 12 536);Iprodione, 3- (3,5-dichlorophenyl) -2,4-dioxo-imidazolidine-1-carboxylic acid isopropylamide (GB 13 12 536);
Myclozolin, (RS)-3-(3,5-Dichlorphenyl)-5-methoxymethyl-5-methyl-1 ,3-oxazolidin-2,4- dion [CAS RN 54864-61-8];Myclozoline, (RS) -3- (3,5-dichlorophenyl) -5-methoxymethyl-5-methyl-1,3-oxazolidine-2,4-dione [CAS RN 54864-61-8];
Procymidon, N-(3,5-Dichlorphenyl)-1 ,2-dimethylcyclopropan-1 ,2-dicarboximid (USProcymidone, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide (US Pat
3,903,090); Vinclozolin, 3-(3,5-Dichlorphenyl)-5-methyl-5-vinyl-oxazolidin-2,4-dion (DE-A3,903,090); Vinclozoline, 3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-oxazolidine-2,4-dione (DE-A
22 07 576);22 07 576);
Ferbam, Eisen(3+)dimethyldithiocarbamat (US 1 ,972,961);Ferbam, iron (3+) dimethyldithiocarbamate (US 1,972,961);
Nabam, Dinatriumethylenbis(dithiocarbamat) (US 2,317,765);Nabam, disodium ethylenebis (dithiocarbamate) (US 2,317,765);
Maneb, Mangan-ethylenbis(dithiocarbamat) (US 2,504,404); Mancozeb, Mangan-ethylenbis(dithiocarbamat)-polymerkomplex-Zinksalz (GBManeb, manganese ethylene bis (dithiocarbamate) (US 2,504,404); Mancozeb, manganese ethylene bis (dithiocarbamate) polymer complex zinc salt (GB
996 264);996 264);
Metam, Methyldithiocarbaminsäure (US 2,791 ,605); Metiram, Zinkammoniat-ethylenbis(dithiocarbamat) (US 3,248,400);Metam, methyldithiocarbamic acid (US 2,791,605); Metiram, zinc ammonium ethylenebis (dithiocarbamate) (US 3,248,400);
Propineb, Zink Propylenbis(dithiocarbamat) Polymer (BE 611 960);Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);
Polycarbamat, Bis(dimethylcarbamodithioato-κS,κS')[μ-[[1 ,2-ethandiylbis[carbamo- dithioato-κS,κS']](2-)]]di[zinc] [CAS RN 64440-88-6]; Thiram, Bis(dimethylthiocarbamoyl)disulfid (DE-A 642 532);Polycarbamate, bis (dimethylcarbamodithioato-κS, κS ') [μ - [[1,2-ethanediylbis [carbamoedithioato-κS, κS']] (2 -)]] di [zinc] [CAS RN 64440-88-6 ]; Thiram, bis (dimethylthiocarbamoyl) disulfide (DE-A 642 532);
Ziram, Dimethyldithiocarbamat [CAS RN 137-30-4];Ziram, dimethyldithiocarbamate [CAS RN 137-30-4];
Zineb, Zink-ethylenbis(dithiocarbamat) (US 2,457,674);Zineb, zinc ethylenebis (dithiocarbamate) (US 2,457,674);
Anilazin, 4,6-Dichlor-N-(2-chlorphenyl)-1 ,3,5-triazin-2-amin (US 2,720,480);Anilazine, 4,6-dichloro-N- (2-chlorophenyl) -1, 3,5-triazin-2-amine (US 2,720,480);
Benomyl, 2-Acetylaminobenzimidazol-1-carbonsäurebutylamid (US 3,631 ,176); Boscalid, 2-Chlor-N-(4'-chlorbiphenyl-2-yl)nicotinamid (EP-A 545 099);Benomyl, 2-acetylaminobenzimidazole-1-carboxylic acid butylamide (US 3,631,176); Boscalid, 2-chloro-N- (4'-chlorobiphenyl-2-yl) nicotinamide (EP-A 545 099);
Carbendazim, (1 H-Benzimidazol-2-yl)-carbaminsäuremethylester (US 3,657,443);Carbendazim, (1 H-benzimidazol-2-yl) -carbamic acid methyl ester (US 3,657,443);
Carboxin, 5,6-Dihydro-2-methyl-N-phenyl-1 ,4-oxathiin-3-carboxamid (US 3,249,499);Carboxin, 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide (US 3,249,499);
Oxycarboxin, 5,6-Dihydro-2-methyl-1 ,4-oxathiin-3-carboxanilid 4,4-dioxid (USOxycarboxine, 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide 4,4-dioxide (US
3,399,214); Cyazofamid, 4-Chlor-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1 H-imidazol-1 -Sulfonamid (CAS RN 120116-88-3];3,399,214); Cyazofamide, 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide (CAS RN 120116-88-3];
Dazomet, 3,5-Dimethyl-1 ,3,5-thiadiazinan-2-thion (Bull. Soc. Chim. Fr. Vol. 15, p. 891Dazomet, 3,5-dimethyl-1,3,5-thiadiazinan-2-thione (Bull Soc Soc. Chim. Fr. Vol. 15, p.891
(1897));(1897));
Diflufenzopyr, 2-{1-[4-(3,5-Difluorphenyl)semicarbazono]ethyl}nicotinsäure [CAS RN 109293-97-2];Diflufenzopyr, 2- {1- [4- (3,5-difluorophenyl) semicarbazono] ethyl} nicotinic acid [CAS RN 109293-97-2];
Dithianon, 5, 10-Dioxo-5, 10-dihydronaphtho[2,3-b][1 ,4]dithiin-2,3-dicarbonitril (GBDithianone, 5,10-dioxo-5,10-dihydronaphtho [2,3-b] [1,4] dithiine-2,3-dicarbonitrile (GB
857 383);857 383);
Famoxadon, (RS)-3-Anilino-5-methyl-5-(4-phenoxyphenyl)-1 ,3-oxazolidin-2,4-dionFamoxadone, (RS) -3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione
[CAS RN 131807-57-3]; Fenamidon, (S)-1-Anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-on [CAS RN[CAS RN 131807-57-3]; Fenamidone, (S) -1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one [CAS RN
161326-34-7];161326-34-7];
Fenarimol, α-(2-Chlorphenyl)-α-(4-chlorphenyl)-5-pyrimidinmethanol (GB 12 18 623);Fenarimol, α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidinemethanol (GB 12 18 623);
Fuberidazol, 2-(2-Furanyl)-1 H-benzimidazol (DE-A 12 09 799);Fuberidazole, 2- (2-furanyl) -1H-benzimidazole (DE-A 12 09 799);
Flutolanil, α,α,α-Trifluor-3'-isopropoxy-o-toluanilid (JP 1104514); Furametpyr, 5-Chlor-N-(1 ,3-dihydro-1 , 1 ,3-trimethyl-4-isobenzofuranyl)-1 ,3-dimethyl-1 H- pyrazol-4-carboxamid [CAS RN 123572-88-3];Flutolanil, α, α, α-trifluoro-3'-isopropoxy-o-toluanilide (JP 1104514); Furametpyr, 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88-3 ];
Isoprothiolan, Diisopropyl 1 ,3-dithiolan-2-ylidenmalonat (Proc. Insectic. Fungic. Conf.Isoprothiolane, diisopropyl 1, 3-dithiolan-2-ylidene malonate (Proc. Insectic. Fungic. Conf.
8., Bd. 2, S. 715 (1975));8, Vol. 2, p. 715 (1975));
Mepronil, 3'-lsopropoxy-o-toluanilid (US 3,937,840); Nuarimol, α-(2-Chlorphenyl)-α-(4-fluorphenyl)-5-pyrimidinmethanol (GB 12 18 623);Mepronil, 3'-isopropoxy-o-toluanilide (US 3,937,840); Nuarimol, α- (2-chlorophenyl) -α- (4-fluorophenyl) -5-pyrimidinemethanol (GB 12 18 623);
Fluopicolid (Picobenzamid), 2,6-Dichlor-N-(3-chlor-5-trifluormethyl-pyridin-2-ylmethyl)- benzamid (WO 99/42447);Fluopicolide (picobenzamide), 2,6-dichloro-N- (3-chloro-5-trifluoromethylpyridin-2-ylmethyl) benzamide (WO 99/42447);
Probenazol, 3-Allyloxy-1 ,2-benzothiazol 1 ,1-dioxid (Agric. Biol. Chem. 37, S. 737Probenazole, 3-Allyloxy-1,2-benzothiazole 1,1-dioxide (Agric., Biol. Chem. 37, p
(1973); Proquinazid, 6-lod-2-propoxy-3-propylquinazolin-4(3H)-on (WO 97/48684);(1973); Proquinazide, 6-iodo-2-propoxy-3-propylquinazolin-4 (3H) -one (WO 97/48684);
Pyrifenox, 2',4'-Dichlor-2-(3-pyridyl)acetophenon (EZ)-O-methyloxim (EP 49 854);Pyrifenox, 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone (EZ) -O-methyloxime (EP 49 854);
Pyroquilon, 1,2,5,6-Tetrahydropyrrolo[3,2,1-ij]quinolin-4-on (GB 139 43 373); Quinoxyfen, 5,7-Dichlor-4-(4-fluorphenoxy)quinolin (US 5,240,940);Pyroquilone, 1,2,5,6-tetrahydropyrrolo [3,2,1-ij] quinolin-4-one (GB 139 43 373); Quinoxyfen, 5,7-dichloro-4- (4-fluorophenoxy) quinoline (US 5,240,940);
Silthiofam, N-AllyM.S-dimethyl^trimethylsilyOthiophen-S-carboxamid [CAS RNSilthiofam, N-AllyM, S-dimethyl, trimethylsilythiophene-S-carboxamide [CAS RN
175217-20-6];175217-20-6];
Thiabendazol, 2-(1 ,3-Thiazol-4-yl)benzimidazol (US 3,017,415); Thifluzamid, 2',6'-Dibrom-2-methyl-4'-trifluornnethoxy-4-trifluornnethyl-1 ,3-thiazol-5- carboxanilid [CAS RN 130000-40-7];Thiabendazole, 2- (1,3-thiazol-4-yl) benzimidazole (US 3,017,415); Thifluzamide, 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4-trifluoromethyl-1, 3-thiazole-5-carboxanilide [CAS RN 130000-40-7];
Thiophanat-methyl, 1 ,2-Phenylenbis(iminocarbonothioyl)bis(dimethylcarbamat) (DE-AThiophanate-methyl, 1, 2-phenylenebis (iminocarbonothioyl) bis (dimethylcarbamate) (DE-A
19 30 540);19 30 540);
Tiadinil, S'-Chlor^'-dimethyl-I ^S-thiadiazol-δ-carboxanilid [CAS RN 223580-51-6]; Tricyclazol, 5-Methyl-1 ,2,4-triazolo[3,4-b][1 ,3]benzothiazol [CAS RN 41814-78-2];Tiadinil, S'-chloro '' - dimethyl-1S-thiadiazole-6-carboxanilide [CAS RN 223580-51-6]; Tricyclazole, 5-methyl-1,2,4-triazolo [3,4-b] [1,3] benzothiazole [CAS RN 41814-78-2];
Triforin, N,N'-{Piperazin-1 ,4-diylbis[(trichlormethyl)methylen]}diformamid (DE-ATriforin, N, N '- {piperazine-1, 4-diylbis [(trichloromethyl) methylene] diformamide (DE-A
19 01 421);19 01 421);
5-Chlor-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluor-phenyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidin (WO 98/46607); Bordeauxbrühe, Mischung aus CuSO4 x 3Cu(OH)2 x 3CaSO4 [CAS RN 8011-63-0];5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine (WO 98/46607); Bordeaux broth, mixture of CuSO 4 .3Cu (OH) 2 .3CaSO 4 [CAS RN 8011-63-0];
Kupferacetat, Cu(OCOCH3)2 [CAS RN 8011-63-0];Copper acetate, Cu (OCOCH 3 ) 2 [CAS RN 8011-63-0];
Kupferoxychlorid, Cu2CI(OH)3 [CAS RN 1332-40-7];Copper oxychloride, Cu 2 Cl (OH) 3 [CAS RN 1332-40-7];
Basisches Kupfersulfat, CuSO4 [CAS RN 1344-73-6];Basic copper sulfate, CuSO 4 [CAS RN 1344-73-6];
Binapacryl, (RS)-2-sec-Butyl-4,6-dinitrophenyl 3-methylcrotonat [CAS RN 485-31-4]; Dinocap, Mischung aus 2,6-Dinitro-4-octylphenylcrotonat und 2,4-Dinitro-6-octyl- phenylcrotonat, wobei "octyl" eine Mischung aus 1-Methylheptyl, 1-Ethylhexyl undBinapacryl, (RS) -2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate [CAS RN 485-31-4]; Dinocap, a mixture of 2,6-dinitro-4-octylphenylcrotonat and 2,4-dinitro-6-octyl-phenylcrotonat, where "octyl" is a mixture of 1-methylheptyl, 1-ethylhexyl and
1-Propylpentyl ist (US 2,526,660);1-propylpentyl is (US 2,526,660);
Dinobuton, (RS)-2-sec-Butyl-4,6-dinitrophenyl-isopropyl-carbonat [CAS RN 973-21-7];Dinobutone, (RS) -2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate [CAS RN 973-21-7];
Nitrothal-isopropyl, diisopropyl-5-nitroisophthalat (Proc. Br. Insectic. Fungic. Conf. 7., Bd. 2, S. 673 (1973));Nitrothal isopropyl, diisopropyl 5-nitroisophthalate (Proc. Br. Insectic., Fungic, Conf., 7: 2, 673 (1973));
Fenpiclonil, 4-(2,3-Dichlorphenyl)-1 H-pyrrol-3-carbonitril (Proc. 1988 Br. Crop Prot.Fenpiclonil, 4- (2,3-dichlorophenyl) -1H-pyrrole-3-carbonitrile (Proc., 1988 Br. Crop Prot.
Conf. - Pests Dis., Bd. 1 , S. 65);Conf. - Pests Dis., Vol. 1, p. 65);
Fludioxonil, 4-(2,2-Difluorbenzo[1 ,3]dioxol-4-yl)-1 H-pyrrol-3-carbonitril (The PesticideFludioxonil, 4- (2,2-difluorobenzo [1,3] dioxol-4-yl) -1H-pyrrole-3-carbonitrile (The Pesticide
Manual, Hrsg.: The British Crop Protection Council, 10. Auflage 1995, S. 482); Acibenzolar-S-methyl, Methyl 1,2,3-benzothiadiazol-7-carbothioat [CAS RN 135158-Manual, Ed .: The British Crop Protection Council, 10th Edition 1995, p. 482); Acibenzolar-S-methyl, methyl 1,2,3-benzothiadiazole-7-carbothioate [CAS RN 135158-
54-2];54-2];
Flubenthiavalicarb (Benthiavalicarb), {(S)-1-[(1 R)-1-(6-Fluorbenzothiazol-2-yl)- ethylcarbamoyl]-2-methylpropyl}-carbaminsäureisopropylester (JP-A 09/323 984);Flubenthiavalicarb (benthiavalicarb), {(S) -1 - [(1 R) -1- (6-fluorobenzothiazol-2-yl) ethylcarbamoyl] -2-methylpropyl} -carbamic acid isopropyl ester (JP-A 09/323 984);
Carpropamid, 2,2-Dichlor-N-[1 -(4-chlorphenyl)ethyl]-1 -ethyl-3-methylcyclopropan- carboxamid [CAS RN 104030-54-8];Carpropamide, 2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropane carboxamide [CAS RN 104030-54-8];
Chlorthalonil, 2,4,5,6-Tetrachlorisophthalonitril (US 3,290,353);Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
Cyflufenamid, (Z)-N-[α-(Cyclopropylmethoxyimino)-2,3-difluor-6-(trifluormethyl)benzyl]-Cyflufenamide, (Z) -N- [α- (Cyclopropylmethoxyimino) -2,3-difluoro-6- (trifluoromethyl) benzyl] -
2-phenylacetamid (WO 96/19442);2-phenylacetamide (WO 96/19442);
Cymoxanil, 1-(2-Cyano-2-methoxyiminoacetyl)-3-ethylhamstoff (US 3,957,847); Diclomezin, 6-(3,5-Dichlorphenyl-p-tolyl)pyridazin-3(2H)-on (US 4,052,395);Cymoxanil, 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (US 3,957,847); Diclomethine, 6- (3,5-dichlorophenyl-p-tolyl) pyridazine-3 (2H) -one (US 4,052,395);
Diclocymet, (RS)-2-Cyano-N-[(R)-1-(2,4-dichlorphenyl)ethyl]-3,3-dimethylbutyramidDiclocymet, (RS) -2-cyano-N - [(R) -1- (2,4-dichlorophenyl) ethyl] -3,3-dimethylbutyramide
[CAS RN 139920-32-4]; Diethofencarb, Isopropyl 3,4-diethoxycarbanilat (EP-A 78 663);[CAS RN 139920-32-4]; Diethofencarb, isopropyl 3,4-diethoxycarbanilate (EP-A 78 663);
Edifenphos, O-Ethyl S,S-diphenyl phosphorodithioat (DE-A 14 93 736);Edifenphos, O-ethyl S, S-diphenyl phosphorodithioate (DE-A 14 93 736);
Ethaboxam, N-(Cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazolcarboxannidEthaboxam, N- (cyano-2-thienylmethyl) -4-ethyl-2- (ethylamino) -5-thiazolecarboxannide
(EP-A 639 574); Fenhexamid, N-(2,3-dichlor-4-hydroxyphenyl)-1-methylcyclohexancarboxamid (Proc.(EP-A 639 574); Fenhexamide, N- (2,3-dichloro-4-hydroxyphenyl) -1-methylcyclohexanecarboxamide (Proc.
Br. Crop Prot. Conf. - Pests Dis., 1998, Bd. 2, S. 327);Br. Crop Prot. Conf. - Pests Dis., 1998, vol. 2, p. 327);
Fentin-acetat, Triphenylzinn (US 3,499,086);Fentin acetate, triphenyltin (US 3,499,086);
Fenoxanil, N-(1-Cyano-1 ,2-dimethylpropyl)-2-(2,4-dichlorphenoxy)propanamid (EP-AFenoxanil, N- (1-cyano-1,2-dimethylpropyl) -2- (2,4-dichlorophenoxy) propanamide (EP-A
262 393); Ferimzon, (Z)-2'-Methylacetophenon-4,6-dimethylpyrimidin-2-ylhydrazon [CAS RN262 393); Ferimzone, (Z) -2'-methylacetophenone-4,6-dimethylpyrimidin-2-ylhydrazone [CAS RN
89269-64-7];89269-64-7];
Fluazinam, S-Chlor-N-^-chlor^.β-dinitro^-^rifluormethyOphenylJ-S-^rifluormethyl)^- pyridinamin (The Pesticide Manual, Hrsg.: The British Crop Protection Council, 10.Fluazinam, S-chloro-N - ^ - chloro-β, -β-dinitro ^ -rifluoromethyl-phenyl-S-rifluoromethyl) -pyridinamine (The Pesticide Manual, Ed. The British Crop Protection Council, 10.
Auflage 1995, S. 474); Fosetyl, Fosetyl-Aluminum, Ethylphosphonat (FR 22 54 276);Edition 1995, p. 474); Fosetyl, Fosetyl Aluminum, Ethyl Phosphonate (FR 22 54 276);
Iprovalicarb, [(1S)-2-Methyl-1-(1-p-tolyl-ethylcarbamoyl)-propyl]carbaminsäure- isopropylester (EP-A 472 996);Iprovalicarb, [(1S) -2-methyl-1- (1-p-tolyl-ethylcarbamoyl) -propyl] -carbamic acid isopropyl ester (EP-A 472 996);
Hexachlorbenzol (C. R. Seances Acad. Agric. Fr., Vol. 31 , S. 24 (1945);Hexachlorobenzene (C.R. Seances Acad. Agric. Fr., Vol. 31, p. 24 (1945);
Mandipropamid, (RS)-2-(4-Chlorphenyl)-N-[3-methoxy-4-(prop-2-ynyloxy)phenethyl]-2- (prop-2-ynyloxy)acetamid (WO 03/042166);Mandipropamide, (RS) -2- (4-chlorophenyl) -N- [3-methoxy-4- (prop-2-ynyloxy) phenethyl] -2- (prop-2-ynyloxy) acetamide (WO 03/042166);
Metrafenon, 3'-Brom-2,3,4,6'-tetramethoxy-2',6-dimethylbenzophenon (US 5,945,567);Metrafenone, 3'-bromo-2,3,4,6'-tetramethoxy-2 ', 6-dimethylbenzophenone (US 5,945,567);
Pencycuron, i-^-ChlorbenzyO-i-cyclopentyl-S-phenylhamstoff (DE-A 27 32 257);Pencycuron, i - ^ - ChlorbenzyO-i-cyclopentyl-S-phenylurea (DE-A 27 32 257);
Penthiopyrad, (RS)-N-[2-(1 ,3-Dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluormethyl)-1 H- pyrazol-4-carboxamid (JP 10/130268); Propamocarb, 3-(Dimethylamino)propylcarbaminsäureisopropylester (DE-A 1567 169);Penthiopyrad, (RS) -N- [2- (1, 3-dimethylbutyl) -3-thienyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (JP 10/130268); Propamocarb, 3- (dimethylamino) propylcarbamic acid isopropyl ester (DE-A 1567 169);
Phthalid (DE-A 16 43 347);Phthalide (DE-A 16 43 347);
Toloclofos-methyl, O-2,6-Dichlor-p-tolyl O,O-dimethyl phosphorothioat (GB 14 67 561);Toloclofos-methyl, O-2,6-dichloro-p-tolyl O, O-dimethyl phosphorothioate (GB 14 67 561);
Quintozen, Pentachlornitrobenzol (DE-A 682 048);Quintoene, pentachloronitrobenzene (DE-A 682 048);
Zoxamid, (RS)-3,5-Dichlor-N-(3-chlor-1 -ethyl-1 -methyl-2-oxopropyl)-p-toluamid [CAS RN 156052-68-5];Zoxamide, (RS) -3,5-dichloro-N- (3-chloro-1-ethyl-1-methyl-2-oxopropyl) -p-toluamide [CAS RN 156052-68-5];
Captafol, N-(1,1 ,2,2-Tetrachlorethylthio)cyclohex-4-en-1 ,2-dicarboximidCaptafol, N- (1,1,2,2-tetrachloroethylthio) cyclohex-4-ene-1,2-dicarboximide
(Phytopathology 52, S. 754 (1962));(Phytopathology 52, p. 754 (1962));
Captan, N-(Trichlormethylthio)cyclohex-4-en-1 ,2-dicarboximid (US 2,553,770);Captan, N- (trichloromethylthio) cyclohex-4-ene-1,2-dicarboximide (US 2,553,770);
Dichlofluanid, N-Dichlorfluormethylthio-N',N'-dimethyl-N-phenylsulfannid (DE-A 11 93 498);Dichlofluanid, N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulfannide (DE-A 11 93 498);
Folpet, N-(Trichlormethylthio)phthalimid (US 2,553,770);Folpet, N- (trichloromethylthio) phthalimide (US 2,553,770);
Tolylfluanid, N-Dichlorfluormethylthio-N',N'-dimethyl-N-p-tolylsulfannid (DE-ATolylfluanid, N-dichlorofluoromethylthio-N ', N'-dimethyl-N-p-tolylsulfannide (DE-A
11 93 498);11 93 498);
Dimethomorph, 3-(4-Chlorphenyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-yl-propenon (EP-A 120 321);Dimethomorph, 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) -1-morpholin-4-yl-propenone (EP-A 120 321);
Flumetover, 2-(3,4-Dimethoxyphenyl)-N-ethyl-α,α,α-trifluor-N-methyl-p-toluannidFlumetover, 2- (3,4-dimethoxyphenyl) -N-ethyl-α, α, α-trifluoro-N-methyl-p-toluanide
[AGROW Nr. 243, 22 (1995)]; Flumorph, 3-(4-Fluorphenyl)-3-(3,4-dimethoxyphenyl)-1 -morpholin-4-yl-propenon (EP-A[AGROW No. 243, 22 (1995)]; Flumorph, 3- (4-fluorophenyl) -3- (3,4-dimethoxyphenyl) -1-morpholin-4-yl-propenone (EP-A
860 438);860 438);
4-Difluormethyl-2-methyl-thiazol-5-carbonsäure-N-(4'-bronn-biphenyl-2-yl)-annicl,4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-bronn-biphenyl-2-yl) -annicl,
4-Difluornnethyl-2-nnethyl-thiazol-5-carbonsäure-N-(4'-trifluornnethyl-biphenyl-2-yl)-annid, 4-Difluormethyl-2-methyl-thiazol-5-carbonsäure-N-(4'-chlor-3'-fluor-biphenyl-2-yl)-annicl,4-Difluoroethyl-2-methylthiazole-5-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -annide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4 ' -chloro-3'-fluoro-biphenyl-2-yl) -annicl,
3-Difluomnethyl-1-methyl-pyrazol-4-carbonsäure-N-(3',4'-dichlor-4-fluor-biphenyl-2-yl)- amid (WO 03/66610);3-Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid N- (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide (WO 03/66610);
3,4-Dichlor-isothiazol-5-carbonsäure-N-(2-cyano-phenyl)-amid (WO 99/24413);3,4-dichloro-isothiazole-5-carboxylic acid N- (2-cyanophenyl) -amide (WO 99/24413);
N-(2-(4-[3-(4-Chlor-phenyl)-prop-2-ynyloxy]-3-methoxy-phenyl)-ethyl)-2-methan- sulfonylamino-3-methyl-butyrannid, N-(2-(4-[3-(4-Chlor-phenyl)-prop-2-ynyloxy]-3- methoxy-phenyl)-ethyl)-2-ethansulfonylamino-3-nnethyl-butyrannid (WO 04/49804);N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino-3-methylbutyrannide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethanesulfonylamino-3-methyl-butyrannide (WO 04/49804);
3-[5-(4-Chlor-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridin (EP-A 10 35 122);3- [5- (4-Chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine (EP-A 10 35 122);
2-Butoxy-6-iodo-3-propyl-chromen-4-on (WO 03/14103);2-butoxy-6-iodo-3-propyl-chromen-4-one (WO 03/14103);
3-(3-Brom-6-fluor-2-methyl-indol-1 -sulfonyl)-[1 ,2,4]triazol-1 -sulfonsäure-dimethylamid (EP-A 10 31 571);3- (3-bromo-6-fluoro-2-methyl-indol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide (EP-A 10 31 571);
(2-Chlor-5-[1-(3-methyl-benzyloxyimino)-ethyl]-benzyl)-carbanninsäurennethylester,(2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbanninsäurennethylester,
(2-Chlor-5-[1-(6-methyl-pyridin-2-ylmethoxyinnino)-ethyl]-benzyl)-carbanninsäure- methylester (EP-A 12 01 648);(2-Chloro-5- [1- (6-methylpyridin-2-ylmethoxyinnino) ethyl] benzyl) -carbannic acid methyl ester (EP-A 12 01 648);
3-(4-Chlor-phenyl)-3-(2-isopropoxy-carbonylamino-3-methyl-butyrylannino)- propionsäure-methylester (EP-A 10 28 125);Methyl 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methylbutyrylannino) propionate (EP-A 10 28 125);
Azoxystrobin, 2-{2-[6-(2-Cyano-1 -vinyl-penta-1 ,3-dienyloxy)-pyrimidin-4-yloxy]-phenyl}-Azoxystrobin, 2- {2- [6- (2-cyano-1-vinyl-penta-1,3-dienyloxy) -pyrimidin-4-yloxy] -phenyl} -
3-methoxy-acrylsäuremethylester (EP-A 382 375);3-methoxy-acrylic acid methyl ester (EP-A 382 375);
Dimoxystrobin, (E)-2-(Methoxyimino)-N-methyl-2-[α-(2,5-xylyloxy)-o-tolyl]acetannidDimoxystrobin, (E) -2- (methoxyimino) -N-methyl-2- [α- (2,5-xylyloxy) -o-tolyl] -acetannide
(EP-A 477 631); Fluoxastrobin, (E)-{2-[6-(2-Chlorphenoxy)-5-fluorpyrimidin-4-yloxy]phenyl}(5,6-dihydro-(EP-A 477 631); Fluoxastrobin, (E) - {2- [6- (2-chlorophenoxy) -5-fluoropyrimidin-4-yloxy] phenyl} (5,6-dihydroxy)
1 ,4,2-dioxazin-3-yl)methanon-O-nnethyloxinn (WO 97/27189);1, 4,2-dioxazin-3-yl) methanone-O-nethyloxine (WO 97/27189);
Kresoxim-methyl, (E)-Methoxyimino[α-(o-tolyloxy)-o-tolyl]essigsäuremethylester (EP-AKresoxim-methyl, (E) -methoxyimino [α- (o-tolyloxy) -o-tolyl] acetic acid methyl ester (EP-A
253 213);253 213);
Metominostrobin, (E)-2-(Methoxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamid (EP-A 398 692);Metominostrobin, (E) -2- (methoxyimino) -N-methyl-2- (2-phenoxyphenyl) acetamide (EP-A 398 692);
Orysastrobin, (2E)-2-(Methoxyimino)-2-{2-[(3E,5E,6E)-5-(methoxyinnino)-4,6-dinnethyl-Orysastrobin, (2E) -2- (methoxyimino) -2- {2 - [(3E, 5E, 6E) -5- (methoxyinnino) -4,6-dinethy-
2,8-dioxa-3,7-diazanona-3,6-dien-1-yl]phenyl}-N-methylacetannid (WO 97/15552);2,8-dioxa-3,7-diazanon-3,6-dien-1-yl] phenyl} -N-methylacetanide (WO 97/15552);
Picoxystrobin, 3-Methoxy-2-[2-(6-trifluormethyl-pyridin-2-yloxynnethyl)-phenyl]-acryl- säuremethylester (EP-A 278 595); Pyraclostrobin, N-{2-[1-(4-Chlorphenyl)-1 H-pyrazol-3-yloxymethyl]phenyl}(N- methoxy)carbaminsäurennethylester (WO 96/01256);Picoxystrobin, 3-methoxy-2- [2- (6-trifluoromethylpyridin-2-yloxyn-ethyl) -phenyl] -acrylic acid methyl ester (EP-A 278 595); Pyraclostrobin, N- {2- [1- (4-chlorophenyl) -1H-pyrazol-3-yloxymethyl] phenyl} (N-methoxy) carbamic acid, ethyl ester (WO 96/01256);
Trifloxystrobin, (E)-Methoxyimino-{(E)-α-[1-(α,α,α-trifluor-nn-tolyl)ethylidenanninooxy]-o- tolyl}essigsäuremethylester (EP-A 460 575);Trifloxystrobin, (E) -methoxyimino-{(E) -α- [1- (α, α, α-trifluoro-n-tolyl) -ethylidene-amino-oxy] -o-tolyl} -acetic acid methyl ester (EP-A 460 575);
2-[ortho-(2,5-Dimethylphenyl-oxynnethylen)phenyl]-3-nnethoxy-acrylsäurennethylester (EP-A 226 917);2- [ortho- (2,5-dimethylphenyl-oxynethylene) -phenyl] -3-nethoxy-acrylic acid ethyl ester (EP-A 226 917);
5-Chlor-7-(4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluor-phenyl)-[1 ,2,4]triazolo[1 ,5-a]pyri- midin (WO 98/46608); 3,4-Dichlor-N-(2-cyanophenyl)-isothiazol-5-carbonsäureamid (WO 99/24413); Verbindungen der Formel IM (WO 04/049804);5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine (WO 98/46608); 3,4-dichloro-N- (2-cyanophenyl) -isothiazole-5-carboxylic acid amide (WO 99/24413); Compounds of formula IM (WO 04/049804);
N-(2-(4-[3-(4-Chlor-phenyl)-prop-2-ynyloxy]-3-methoxy-phenyl)-ethyl)-2-methan- sulfonylamino-3-methyl-butyramid und N-(2-(4-[3-(4-Chlor-phenyl)-prop-2-ynyloxy]-3- methoxy-phenyl)-ethyl)-2-ethansulfonylamino-3-methyl-butyrannid (WO 03/66609); 2-Butoxy-6-iodo-3-propyl-chromen-4-on der Formel IV (WO 03/14103); 3-(3-Brom-6-fluor-2-methyl-indol-1 -sulfonyl)-[1 ,2,4]triazol-1 -sulfonsäuredimethylamid der Formel V (WO 03/053145);N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino-3-methylbutyramide and N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethanesulfonylamino-3-methyl-butyrannide (WO 03/66609); 2-butoxy-6-iodo-3-propyl-chromen-4-one of the formula IV (WO 03/14103); 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide of the formula V (WO 03/053145);
3-(4-Chlor-phenyl)-3-(2-isopropoxycarbonylamino-3-methyl-butyrylamino)- propansäuremethylester der Formel VI (EP-A 1028125).Methyl 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methylbutyrylamino) propanoate of the formula VI (EP-A 1028125).
Im Hinblick auf eine Senkung der Aufwandmengen und eine Verbreiterung des Wirkungsspektrums der Verbindungen I und Il lagen der vorliegenden Erfindung Mischungen als Aufgabe zugrunde, die bei verringerter Gesamtmenge an ausgebrachten Wirk- Stoffen eine verbesserte Wirkung gegen Schadpilze, insbesondere für bestimmte Indikationen, zeigen.With regard to a reduction of the application rates and a widening of the spectrum of action of the compounds I and II, the present invention mixtures were the object of an improved effect against harmful fungi, especially for certain indications show with reduced total amount of active substances.
Demgemäss wurden die eingangs definierten Mischungen der Wirkstoffe I und Il gefunden. Es wurde außerdem gefunden, dass sich bei gleichzeitiger, und zwar gemein- samer oder getrennter Anwendung mindestens einer Verbindung I und von mindestens einem der Wirkstoffe II, oder der Verbindung(en) I und mindestens einem der Wirkstoffe Il nacheinander, Schadpilze besser bekämpfen lassen als mit den Einzelverbindungen allein (synergistische Mischungen).Accordingly, the mixtures of active ingredients I and II defined above were found. It has also been found that it is possible to combat harmful fungi more effectively in the simultaneous, combined or separate use of at least one compound I and of at least one of the active compounds II, or the compound (s) I and at least one of the active compounds II with the individual compounds alone (synergistic mixtures).
Die Verbindungen I lassen sich als Synergisten für eine Vielzahl verschiedener fungizider Wirkstoffe verwenden. Durch gleichzeitige gemeinsame oder getrennte Anwendung von Verbindung(en) I mit mindestens einem Wirkstoff Il wird die fungizide Wirksamkeit in überadditivem Maße erhöht.The compounds I can be used as synergists for a variety of different fungicidal agents. By simultaneous joint or separate application of compound (s) I with at least one active ingredient II, the fungicidal activity is increased to a superadditive extent.
Die Verbindungen I können in verschiedenen Kristallmodifikationen vorliegen, die sich in der biologischen Wirksamkeit unterscheiden können.The compounds I can be present in various crystal modifications, which may differ in their biological activity.
In Formel I steht Halogen für Fluor, Chlor, Brom oder Jod, vorzugsweise für Fluor oder Chlor;In formula I, halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;
Ci-C4-Alkyl steht für Methyl, Ethyl, n-Propyl, 1-Methylethyl, n-Butyl, 1-Methylpropyl, 2- Methylpropyl oder 1 ,1-Dimethylethyl, vorzugsweise für Methyl oder Ethyl;C 1 -C 4 -alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl, preferably methyl or ethyl;
Ci-C4-Halogenalkyl steht für einen teilweise oder vollständig halogenierten Ci-C4- Alkylrest, wobei das/die Halogenatom(e) insbesondere Fluor, Chlor und/oder Brom ist/sind, also z.B. Chlormethyl, Brommethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluormethyl, 1-Chlorethyl, 1-Bromethyl, 1-Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2-Trifluor- ethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluorethyl, 2,2-Dichlor-2-fluorethyl, 2,2,2-Tri- chlorethyl, Pentafluorethyl, Heptafluorpropyl oder Nonafluorbutyl, insbesondere für Ha- logenmethyl, besonders bevorzugt für CH2-CI, CH(CI)2, CH2-F, CH(F)2, CF3, CHFCI, CF2CI oder CF(CI)2.Ci-C 4 haloalkyl is a partially or completely halogenated Ci-C 4 - alkyl group, wherein the / the halogen atom (s) is especially fluorine, chlorine and / or bromine / are eg chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, 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, pentafluoroethyl, heptafluoropropyl or nonafluorobutyl, especially for halomethyl, particularly preferably CH 2 -CI, CH (CI) 2 , CH 2 -F , CH (F) 2 , CF 3 , CHFCI, CF 2 Cl or CF (CI) 2 .
Die 1-Methylpyrazol-4-ylcarbonsäureanilide der Formel I sind aus der WO 99/09013, JP 09/132567 und der älteren Anmeldung PCT/EP2006/062219 bekannt oder auf die dort beschriebene Weise herstellbar.The 1-methylpyrazol-4-ylcarbonsäureanilide of formula I are known from WO 99/09013, JP 09/132567 and the earlier application PCT / EP2006 / 062219 or can be prepared in the manner described therein.
Die Verbindungen I, bei denen X für Schwefel steht, sind beispielsweise durch Schwefelung der entsprechenden Verbindungen I, bei denen X für Sauerstoff steht, herstellbar (vgl. z.B. D. Petrova & K. Jakobcic, Croat. Chem. Acta 48, 49 (1976) sowie die WO 01/42223).The compounds I in which X is sulfur can be prepared, for example, by sulfurization of the corresponding compounds I in which X is oxygen (cf., for example, D. Petrova & K. Jakobcic, Croat. Chem. Acta 48, 49 (1976 ) and WO 01/42223).
Unter den i-Methylpyrazol-4-ylcarbonsäureaniliden I sind einerseits diejenigen bevorzugt, bei denen X Sauerstoff bedeutet.Among the i-methylpyrazol-4-ylcarbonsäureaniliden I on the one hand, those are preferred in which X is oxygen.
Andererseits sind diejenigen Verbindungen I bevorzugt, bei denen X für Schwefel steht.On the other hand, those compounds I are preferred in which X is sulfur.
Für die erfindungsgemäßen Mischungen sind Verbindungen der Formel I bevorzugt, bei denen R1 für Ci-C4-Halogenalkyl, vorzugsweise Halogenmethyl, insbesondere CHF2 oder CF3, steht.For the mixtures according to the invention, preference is given to compounds of the formula I in which R 1 is C 1 -C 4 -haloalkyl, preferably halomethyl, in particular CHF 2 or CF 3 .
Bevorzugt sind ferner Verbindungen I, bei denen R2 für Wasserstoff, Fluor oder Chlor, insbesondere Wasserstoff, steht.Preference is further given to compounds I in which R 2 is hydrogen, fluorine or chlorine, in particular hydrogen.
Besonders bevorzugt sind die in der folgenden Tabelle aufgelisteten Verbindungen I:Particular preference is given to the compounds I listed in the following table:
Tabelle 1Table 1
Ganz besonders bevorzugt sind 1-Methyl-3-trifluormethyl-1 H-pyrazol-4-carbonsäure-N- (4'-trifluormethyl-biphen-2-yl)-amid, 3-Difluormethyl-1 -methyl-1 H-pyrazol-4- carbonsäure-N-(4'-trifluormethyl-biphen-2-yl)-amid, 1-Methyl-3-trifluormethyl-5-fluor- 1 H-pyrazol-4-carbonsäure-N-(4'-trifluormethylbiphenyl-2-yl)-amid, 1 ,3-Dimethyl-5- chlor-1 H-pyrazol-4-carbonsäure-N-(4'-trifluormethylbiphenyl-2-yl)-amid, 1 ,3-Dimethyl- 1 H-pyrazol-4-carbonsäure-N-(4'-trifluormethylbiphenyl-2-yl)-amid, 1 -Methyl-3- fluormethyl-1 H-pyrazol-4-carbonsäure-N-(4'-trifluormethylbiphenyl-2-yl)-annid, 1-Methyl-3-chlordifluormethyl-1 H-pyrazol-4-carbonsäure-N-(4'-trifluormethylbiphenyl-2- yl)-amid und 1-Methyl-3-chlorfluormethyl-1 H-pyrazol-4-carbonsäure-N-(4'- trifluormethylbiphenyl-2-yl)-amid, insbesondere 1-Methyl-3-trifluormethyl-1 H-pyrazol-4- carbonsäure-N-(4'-trifluormethyl-biphen-2-yl)-amid und 3-Difluormethyl-1 -methyl-1 H- pyrazol-4-carbonsäure-N-(4'-trifluormethyl-biphen-2-yl)-amid.Very particular preference is given to 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphen-2-yl) -amide, 3-difluoromethyl-1-methyl-1H-pyrazole -4- carboxylic acid N- (4'-trifluoromethyl-biphen-2-yl) -amide, 1-methyl-3-trifluoromethyl-5-fluoro-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethylbiphenyl -2-yl) amide, 1, 3-dimethyl-5-chloro-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethylbiphenyl-2-yl) -amide, 1, 3-dimethyl-1H pyrazole-4-carboxylic acid N- (4'-trifluoromethylbiphenyl-2-yl) -amide, 1-methyl-3-fluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethylbiphenyl-2-yl ) -annide, 1-methyl-3-chlorodifluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide and 1-methyl-3-chlorofluoromethyl-1H-pyrazole-4 -carboxylic acid N- (4'-trifluoromethylbiphenyl-2-yl) -amide, in particular 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphen-2-yl) -amide and 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphen-2-yl) -amide.
Bevorzugt sind Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der A) Azole.Preference is given to mixtures of a compound of the formula I with at least one active compound selected from the group of A) azoles.
Bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der B) Strobilurine.Preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group of B) strobilurins.
Bevorzugt sind Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der C) Carbonsäureamide.Preference is given to mixtures of a compound of the formula I with at least one active compound selected from the group of C) carboxylic acid amides.
Weiterhin bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindes- tens einem Wirkstoff ausgewählt aus der Gruppe der D) Heterocyclischen Verbindungen.Also preferred are mixtures of a compound of formula I with at least one active ingredient selected from the group of D) heterocyclic compounds.
Weiterhin bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der E) Carbamate.Also preferred are mixtures of a compound of formula I with at least one active ingredient selected from the group of E) carbamates.
Weiterhin bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der F) Sonstigen Fungizide.Also preferred are mixtures of a compound of formula I with at least one active ingredient selected from the group of F) other fungicides.
Weiterhin bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindes- tens einem Wirkstoff ausgewählt aus der Gruppe der A) Azole, ausgewählt aus Cypro- conazol, Difenoconazol, Epoxiconazol, Fluquinconazol, Flusilazol, Flutriafol, Metcon- azol, Myclobutanil, Penconazol, Propiconazol, Prothioconazol, Triadimefon, Triadime- nol, Tebuconazol, Tetraconazol, Triticonazol, Prochloraz, Cyazofamid, Benomyl, Car- bendazim und Ethaboxam.Also preferred are mixtures of a compound of formula I with at least one active ingredient selected from the group of A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole , Prothioconazole, Triadimefon, Triadime- nol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamide, benomyl, carbenzimine and ethaboxam.
Besonders bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der A) Azole, ausgewählt aus Cyproconazol, Difenoconazol, Epoxiconazol, Fluquinconazol, Flusilazol, Flutriafol, Met- conazol, Myclobutanil, Propiconazol, Prothioconazol, Triadimefon, Triadimenol, Tebuconazol, Tetraconazol, Triticonazol, Prochloraz, Cyazofamid, Benomyl und Carbenda- zim.Particular preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group consisting of a) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadimenol , Tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamide, benomyl and carbendazim.
Ganz besonders bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der A) Azole, ausgewählt aus Epoxiconazol, Fluquinconazol, Flutriafol, Metconazol, Tebuconazol, Triticonazol, Prochloraz und Carbendazim.Very particular preference is also given to mixtures of a compound of the formula I with at least one active substance selected from the group of A) azoles selected from epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim.
Bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der B) Strobilurine, ausgewählt aus Azoxystrobin, Dimoxystrobin, Fluoxastrobin, Kresoxim-methyl, Orysastrobin, Picoxystrobin, Pyrac- lostrobin und Trifloxystrobin.Preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group consisting of b) strobilurins selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyracrocrobin and trifloxystrobin.
Besonders bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der B) Strobilurine, ausgewählt aus Kresoxim-methyl, Orysastrobin und Pyraclostrobin.Particular preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group consisting of B) strobilurins selected from kresoxim-methyl, orysastrobin and pyraclostrobin.
Ganz besonders bevorzugt sind auch Mischungen einer Verbindung der Formel I mit Pyraclostrobin.Very particular preference is also given to mixtures of a compound of the formula I with pyraclostrobin.
Bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der C) Carbonsäureamide, ausgewählt aus Fen- hexamid, Metalaxyl, Mefenoxam, Ofurace, Dimethomorph, Flumorph, Fluopicolid (Pico- benzamid), Zoxamid, Carpropamid und Mandipropamid.Preference is also given to mixtures of a compound of the formula I with at least one active substance selected from the group of C) carboxylic acid amides selected from hexadexamide, metalaxyl, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picosamide), zoxamide, carpropamide and mandipropamide ,
Besonders bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der C) Carbonsäureamide, ausgewählt aus Fenhexamid, Metalaxyl, Mefenoxam, Ofurace, Dimethomorph, Zoxamid, und Carpropamid.Particular preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group of C) carboxylic acid amides selected from fenhexamide, metalaxyl, mefenoxam, ofurace, dimethomorph, zoxamide and carpropamide.
Bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der D) Heterocylischen Verbindungen, ausge- wählt aus Fluazinam, Cyprodinil, Fenarimol, Mepanipyrim, Pyrimethanil, Triforin, FIu- dioxonil, Dodemorph, Fenpropimorph, Tridemorph, Fenpropidin, Iprodion, Vinclozolin, Famoxadon, Fenamidon, Probenazol, 5-Chlor-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-tri- fluor-phenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrinnidin, Proquinazid, Acibenzolar-S-methyl, Capta- fol, Folpet, Fenoxanil und Quinoxyfen, insbesondere Fluazinam, Cyprodinil, Fenarimol, Mepanipyrim, Pyrimethanil, Triforin, Fludioxonil, Dodemorph, Fenpropimorph, Tride- morph, Fenpropidin, Iprodion, Vinclozolin, Famoxadon, Fenamidon, Probenazol, Pro- quinazid, Acibenzolar-S-methyl, Captafol, Folpet, Fenoxanil und Quinoxyfen.Preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group consisting of d) heterocyclic compounds selected from fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fi dioxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin , Iprodione, vinclozolin, famoxadone, fenamidone, probenazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-tri- fluorophenyl) - [1,2,4] triazolo [1,5-a] pyrinnidine, proquinazide, acibenzolar-S-methyl, captapol, folpet, fenoxanil and quinoxyfen, in particular fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil , Triforin, fludioxonil, dodemorph, fenpropimorph, tride- morph, fenpropidin, iprodione, vinclozoline, famoxadone, fenamidone, probenazole, pro- quinazide, acibenzolar-S-methyl, captafol, folpet, fenoxanil and quinoxyfen.
Besonders bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der D) Heterocyclischen Verbindungen, ausgewählt aus Pyrimethanil, Dodemorph, Fenpropimorph, Tridemorph, Iprodion, Vinclozolin, 5-Chlor-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluor-phenyl)-Particular preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group consisting of d) heterocyclic compounds selected from pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozoline, 5-chloro-7- (4-methylpiperidine -1-yl) -6- (2,4,6-trifluoro-phenyl) -
[1 ,2,4]triazolo[1 ,5-a]pyrimidin und Quinoxyfen, insbesondere Pyrimethanil, Dodemorph, Fenpropimorph, Tridemorph, Iprodion, Vinclozolin und Quinoxyfen.[1,2,4] triazolo [1,5-a] pyrimidine and quinoxyfen, in particular pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozoline and quinoxyfen.
Bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der E) Carbamate ausgewählt aus Mancozeb, Metiram, Propineb, Thiram, Iprovalicarb, Flubenthiavalicarb und Propamocarb.Preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group consisting of E) carbamates selected from mancozeb, metiram, propineb, thiram, iprovalicarb, flubenthiavalicarb and propamocarb.
Besonders bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der E) Carbamate, ausgewählt aus Mancozeb und Metiram.Particular preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group of E) carbamates selected from mancozeb and metiram.
Bevorzugt sind auch Mischungen einer Verbindung der Formel I mit mindestens einem Wirkstoff ausgewählt aus der Gruppe der F) Sonstigen Fungizide, ausgewählt aus Dithianon, Fentin-Salzen wie Fentin-acetat, Fosetyl, Fosetyl-Aluminium, Phosphoriger Säure und deren Salzen, Chlorthalonil, Dichlofluanid, Thiophanate-Methyl, Kupferace- tat, Kupferhydroxid, Kupferoxychlorid, basisches Kupfersulfat, Schwefel, Cymoxanil, Metrafenon und Spiroxamin.Preference is also given to mixtures of a compound of the formula I with at least one active compound selected from the group of F) other fungicides selected from dithianone, fentin salts such as fentin acetate, fosetyl, fosetyl aluminum, phosphorous acid and their salts, chlorothalonil, dichlofluanide , Thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, cymoxanil, metrafenone and spiroxamine.
Besonders bevorzugt sind auch Mischungen einer Verbindung der Formel I mit min- destens einem Wirkstoff ausgewählt aus der Gruppe der F) Sonstigen Fungizide, ausgewählt aus Phosphoriger Säure und deren Salzen, Chlorthalonil und Metrafenon.Particular preference is also given to mixtures of a compound of the formula I with at least one active substance selected from the group of F) Other fungicides selected from phosphorous acid and its salts, chlorothalonil and metrafenone.
Bevorzugt sind auch Dreiermischungen einer Verbindung der Formel I mit zwei der obengenannten Wirkstoffe II.Also preferred are tri-mixtures of a compound of the formula I with two of the abovementioned active compounds II.
Bevorzugte Wirkstoffkombinationen sind in den folgenden Tabellen 2 bis 8 aufgeführt: Tabelle 2Preferred active substance combinations are listed in the following Tables 2 to 8: Table 2
Wirkstoffkombinationen von Verbindungen I mit Wirkstoffen Il der Gruppe A):Active substance combinations of compounds I with active ingredients II of group A):
Tabelle 3 Table 3
Wirkstoffkombinationen von Verbindungen I mit Wirkstoffen Il der Gruppe B):Active substance combinations of compounds I with active ingredients II of group B):
Tabelle 4Table 4
Wirkstoffkombinationen von Verbindungen I mit Wirkstoffen Il der Gruppe C):Active substance combinations of compounds I with active ingredients II of group C):
Tabelle 5Table 5
Wirkstoffkombinationen von Verbindungen I mit Wirkstoffen Il der Gruppe D):Active substance combinations of compounds I with active ingredients II of group D):
Tabelle 6Table 6
Wirkstoffkombinationen von Verbindungen I mit Wirkstoffen Il der Gruppe E):Active substance combinations of compounds I with active ingredients II of group E):
Tabelle 7Table 7
Wirkstoffkombinationen von Verbindungen I mit Wirkstoffen Il der Gruppe F):Active substance combinations of compounds I with active ingredients II of group F):
Tabelle 8Table 8
Wirkstoffkombinationen von Verbindungen I mit zwei Wirkstoffen II:Active substance combinations of compounds I with two active substances II:
Die Mischungen aus Verbindung(en) I und mindestens einem der Wirkstoffe II, bzw. die gleichzeitige gemeinsame oder getrennte Verwendung mindestens einer Verbindung I mit mindestens einem der Wirkstoffe II, zeichnen sich aus durch eine hervorragende Wirksamkeit gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere aus der Klasse der Ascomyceten, Basidiomyceten, Deuteromyceten und Pero- nosporomyceten (syn. Oomyceten ). Sie sind zum Teil systemisch wirksam und können im Pflanzenschutz als Blatt-, Beiz- und Bodenfungizide eingesetzt werden. Sie können auch zur Saatgutbehandlung verwendet werden.The mixtures of compound (s) I and at least one of the active compounds II, or the simultaneous joint or separate use of at least one compound I with at least one of the active compounds II, are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). They are partially systemically effective and can be used in crop protection as foliar, pickling and soil fungicides. They can also be used for seed treatment.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Weizen, Roggen, Gerste, Hafer, Reis, Mais, Rasen, Bananen, Baumwolle, Soja, Kaffee, Zuckerrohr, Wein, Obst- und Zierpflanzen und Gemüsepflanzen wie Gurken, Bohnen, Tomaten, Kartoffeln und Kürbissen, sowie an den Samen dieser Pflanzen.They are of particular importance for the control of a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, turf, bananas, cotton, soy, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers. Beans, tomatoes, potatoes and pumpkins, as well as the seeds of these plants.
Speziell eignen sie sich zur Bekämpfung folgender Pflanzenkrankheiten:In particular, they are suitable for controlling the following plant diseases:
Alternaria Arten an Gemüse, Raps, Zuckerrüben und Obst und Reis, z.B. A. solani oder A. alternata an Kartoffeln und Tomaten, - Aphanomyces Arten an Zuckerrüben und Gemüse, Ascochyta Arten an Getreide and Gemüse,Alternaria species on vegetables, rapeseed, sugar beets and fruits and rice, e.g. A. solani or A. alternata on potatoes and tomatoes, - Aphanomyces species on sugar beet and vegetables, Ascochyta species on cereals and vegetables,
Bipolaris und Drechslera Arten an Mais, Getreide, Reis und Rasen, z.B. D. maydis an Mais, Blumeria graminis (Echter Mehltau) an Getreide,Bipolaris and Drechslera species on corn, cereals, rice and turf, eg D. maydis on corn, Blumeria graminis (powdery mildew) on cereals,
Botrytis cinerea (Grauschimmel) an Erdbeeren, Gemüse, Blumen und Weinreben,Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and vines,
Bremia lactucae an Salat,Bremia lactucae on salad,
Cercospora Arten an Mais, Sojabohnen, Reis und Zuckerrüben, - Cochliobolus Arten an Mais, Getreide, Reis, z.B. Cochliobolus sativus an Getreide,Cercospora species on corn, soybeans, rice and sugar beets, - Cochliobolus species on maize, cereals, rice, e.g. Cochliobolus sativus on cereals,
Cochliobolus miyabeanus an Reis,Cochliobolus miyabeanus on rice,
Colletotricum Arten an Sojabohnen und Baumwolle,Colletotricum species on soybeans and cotton,
Drechslera Arten, Pyrenophora Arten an Mais, Getreide, Reis und Rasen, z.B. D. teres an Gerste oder D. tritici-repentis an Weizen, - Esca an Weinrebe, verursacht durch Phaeoacremonium chlamydosporium, Ph.Drechslera species, Pyrenophora species on corn, cereals, rice and turf, e.g. D. teres to barley or D. tritici-repentis to wheat, - Esca to grapevine, caused by Phaeoacremonium chlamydosporium, Ph.
Aleophilum und Formitipora punctata (syn. Phellinus punctatus ),Aleophilum and Formitipora punctata (syn. Phellinus punctatus),
Exserohilum Arten an Mais,Exserohilum species on corn,
Erysiphe cichoracearum und Sphaerotheca fuliginea an Gurkengewächsen,Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,
Fusarium und Verticillium Arten an verschiedenen Pflanzen, z.B. F. graminearum oder F. culmorum an Getreide oder F. oxysporum an einer Vielzahl von Pflanzen, z.B. Tomaten,Fusarium and Verticillium species on various plants, e.g. F. graminearum or F. culmorum on cereal or F. oxysporum on a variety of plants, e.g. Tomatoes,
Gaeumanomyces graminis an Getreide,Gaeumanomyces graminis on cereals,
Gibberella Arten an Getreide und Reis (z.B. Gibberella fujikuroi an Reis),Gibberella species on cereals and rice (e.g., Gibberella fujikuroi on rice),
Grainstaining complex an Reis, - Helminthosporium Arten an Mais und Reis,Grainstaining complex on rice, - Helminthosporium species on maize and rice,
Michrodochium nivale an Getreide,Michrodochium nivale on cereals,
Mycosphaerella Arten an Getreide, Bananen und Erdnüssen, z.B. M. graminicola an Weizen oder M. fijiesis an Bananen,Mycosphaerella species on cereals, bananas and peanuts, e.g. M. graminicola on wheat or M. fijiesis on bananas,
Peronospora-Arten an Kohl und Zwiebelgewächsen, z.B. P. brassicae an Kohl oder P. destructor an Zwiebel,Peronospora species on cabbage and bulbous plants, e.g. P. brassicae on cabbage or P. destructor on onion,
Phakopsara pachyrhizi und Phakopsara meibomiae an Sojabohnen,Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans,
Phomopsis Arten an Sojabohnen und Sonnenblumen,Phomopsis species on soybeans and sunflowers,
Phytophthora infestans an Kartoffeln und Tomaten,Phytophthora infestans on potatoes and tomatoes,
Phytophthora Arten an verschiedenen Pflanzen, z.B. P. capsici an Paprika, - Plasmopara viticola an Weinreben,Phytophthora species on various plants, e.g. P. capsici on paprika, - Plasmopara viticola on vines,
Podosphaera leucotricha an Apfel,Podosphaera leucotricha on apple,
Pseudocercosporella herpotrichoides an Getreide,Pseudocercosporella herpotrichoides on cereals,
Pseudoperonospora an verschiedenen Pflanzen, z.B. P. cubensis an Gurke oderPseudoperonospora on various plants, e.g. P. cubensis on cucumber or
P. humili an Hopfen, - Puccinia Arten an verschiedenen Pflanzen, z.B. P. triticina , P. striformins , P. hordei oder P. graminis an Getreide oder P. asparagi an Spargel,P. humili on hops, Puccinia species on various plants, e.g. P. triticina, P. striformins, P. hordei or P. graminis on cereals or P. asparagi on asparagus,
Pyricularia oryzae , Corticium sasakii , Sarocladium oryzae, S. attenuatum, Enty- loma oryzae an Reis,Pyricularia oryzae, Corticium sasakii, Sarocladium oryzae, S. attenuatum, Entlyoma oryzae on rice,
Pyricularia grisea an Rasen und Getreide, - Pythium spp. an Rasen, Reis, Mais, Baumwolle, Raps, Sonnenblumen, Zuckerrüben, Gemüse und anderen Pflanzen, z.B. P. ultiumum an verschiedenen Pflanzen, P. aphanidermatum an Rasen, Rhizoctonia Arten an Baumwolle, Reis, Kartoffeln, Rasen, Mais, Raps, Zuckerrüben, Gemüse und an verschiedenen Pflanzen, z.B. R. solani an Rüben und verschiedenen Pflanzen,Pyricularia grisea on lawn and cereals, - Pythium spp. on grass, rice, maize, cotton, rapeseed, sunflower, sugar beets, vegetables and other plants, eg P. ultiumum on various plants, P. aphanidermatum on lawn, Rhizoctonia species on cotton, rice, potatoes, turf, corn, oilseed rape, sugar beets, vegetables and on various plants, eg R. solani on beets and various plants,
Rhynchosporium secalis an Gerste, Roggen und Triticale, - Sclerotinia Arten an Raps und Sonnenblumen,Rhynchosporium secalis on barley, rye and triticale, - Sclerotinia species on oilseed rape and sunflowers,
Septoria tritici und Stagonospora nodorum an Weizen, Erysiphe (syn. Uncinula) necator an Weinrebe, Setospaeria Arten an Mais und Rasen, Sphacelotheca reilinia an Mais, - Thievaliopsis Arten an Sojabohnen und Baumwolle, Tilletia Arten an Getreide,Septoria tritici and Stagonospora nodorum on wheat, Erysiphe (syn. Uncinula) necator on grapevine, Setospaeria species on maize and turf, Sphacelotheca reilinia on maize, - Thievaliopsis species on soybean and cotton, Tilletia species on cereals,
Ustilago Arten an Getreide, Mais und Zuckerrübe, z.B. U. maydis an Mais, Venturia Arten (Schorf) an Äpfeln und Birnen, z.B. V. inaequalis an Apfel.Ustilago species on cereals, corn and sugar beet, e.g. U. maydis on corn, Venturia species (scab) on apples and pears, e.g. V. inaequalis to apple.
Die erfindungsgemäßen Mischungen eignen sich außerdem zur Bekämpfung von Schadpilzen im Materialschutz (z.B. Holz, Papier, Dispersionen für den Anstrich, Fasern bzw. Gewebe) und im Vorratsschutz. Im Holzschutz finden insbesondere folgende Schadpilze Beachtung: Ascomyceten wie Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriel- Ia spp., Trichurus spp.; Basidiomyceten wie Coniophora spp., Coriolus spp., Gloeophyl- lum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. und Tyromyces spp., Deuteromyceten wie Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoder- ma spp., Alternaria spp., Paecilomyces spp. und Zygomyceten wie Mucor spp., darüber hinaus im Materialschutz folgende Hefepilze: Candida spp. und Saccharomyces cerevisae.The mixtures according to the invention are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In wood preservation, particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriela spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophlum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderm spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
Die Verbindung(en) I mit mindestens einem der Wirkstoffe Il können gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat.The compound (s) I with at least one of the active ingredients II can be applied simultaneously, namely jointly or separately, or in succession, the sequence in the case of separate application generally having no effect on the control result.
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe I bis Il ein, denen man weitere Wirkstoffe gegen Schadpilze oder gegen andere Schädlinge wie Insekten, Spinntiere oder Nematoden oder auch herbizide oder wachstumsregulie- rende Wirkstoffe oder Düngemittel beimischen kann.In the preparation of the mixtures, the pure active ingredients I to II are preferably used, to which other active substances can be added against harmful fungi or against other pests such as insects, spider animals or nematodes or else herbicidal or growth-regulating active substances or fertilizers.
Derartige Mischungen aus drei Wirkstoffen bestehen z.B. aus einer Verbindung der Formel I, insbesondere 1-Methyl-3-trifluormethyl-1 H-pyrazol-4-carbonsäure-N-(4'- trifluormethyl-biphenyl-2-yl)-amid oder 3-Difluormethyl-1-methyl-1 H-pyrazol-4- carbonsäure-N-(4'-trifluormethyl-biphenyl-2-yl)-amid, einem Azol aus der Gruppe A), insbesondere Epoxiconazol, Metconazol, Triticonazol oder Fluquinconazol, und einem Insektizid, wobei insbesondere Fipronil und Neonicotinoide wie Acetamiprid, Clothiani- din, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, und Thiamethoxam in Betracht kommen.Such mixtures of three active ingredients consist, for example, of a compound of the formula I, in particular 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide or 3 -Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide, an azole from group A), in particular epoxiconazole, metconazole, triticonazole or fluquinconazole, and an insecticide, in particular fipronil and neonicotinoids such as acetamiprid, clothiani din, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam.
Üblicherweise kommen Mischungen aus mindestens einer Verbindung I und mindes- tens einem Wirkstoff Il zur Anwendung. Jedoch können auch Mischungen aus mindestens einer Verbindung I mit zwei oder gewünschtenfalls mehreren Aktivkomponenten besondere Vorteile bieten.Usually, mixtures of at least one compound I and at least one active ingredient II are used. However, mixtures of at least one compound I with two or, if desired, several active components can also offer particular advantages.
Als weitere Aktivkomponenten im voranstehenden Sinne kommen besonders die ein- gangs genannten Wirkstoffe Il und insbesondere die voranstehend genannten bevorzugten Wirkstoffe Il in Betracht.Suitable further active components in the above sense are, in particular, the aforementioned active compounds II and in particular the above-mentioned preferred active compounds II.
Die Verbindung(en) I und Wirkstoff(e) Il werden üblicherweise in einem Gewichtsverhältnis von 100:1 bis 1 :100, vorzugsweise 20:1 bis 1 :20, insbesondere 10:1 bis 1 :10, angewandt.The compound (s) I and active compound (II) 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.
Die weiteren Aktivkomponenten werden gewünschtenfalls im Verhältnis von 20:1 bis 1 :20 zu der Verbindung I gemischt.If desired, the further active components are mixed in a ratio of from 20: 1 to 1:20 to give compound I.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen, vor allem bei landwirtschaftlichen Kulturflächen, je nach Art der Verbindungen I und Il sowie des gewünschten Effekts, bei 5 g/ha bis 2000 g/ha, vorzugsweise 20 bis 1500 g/ha, insbesondere 50 bis 1000 g/ha.The application rates of the mixtures according to the invention, especially in agricultural crops, depending on the nature of the compounds I and II and the desired effect, at 5 g / ha to 2000 g / ha, preferably 20 to 1500 g / ha, in particular 50 to 1000 g /Ha.
Die Aufwandmengen für die Verbindung(en) I liegen entsprechend in der Regel bei 1 bis 1000 g/ha, vorzugsweise 10 bis 900 g/ha, insbesondere 20 bis 750 g/ha.The application rates for the compound (s) I are accordingly generally 1 to 1000 g / ha, preferably 10 to 900 g / ha, in particular 20 to 750 g / ha.
Die Aufwandmengen für den Wirkstoff Il liegen entsprechend in der Regel bei 1 bis 2000 g/ha, vorzugsweise 10 bis 1500 g/ha, insbesondere 40 bis 1000 g/ha.The application rates for the active compound II are accordingly generally from 1 to 2000 g / ha, preferably from 10 to 1500 g / ha, in particular from 40 to 1000 g / ha.
Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 1 bis 1000 g pro 100 kg Saatgut, vorzugsweise 1 bis 750 g pro 100 kg, insbesondere 5 bis 500 g pro 100 kg Saatgut, verwendet.In the seed treatment, application rates of mixture of 1 to 1000 g per 100 kg of seed, preferably 1 to 750 g per 100 kg, in particular 5 to 500 g per 100 kg of seed are generally used.
Das Verfahren zur Bekämpfung von Schadpilzen erfolgt durch die getrennte oder gemeinsame Applikation von Verbindung(en) I und Wirkstoffen) II, oder einer Mischung aus Verbindung(en) I und mindestens einem der Wirkstoffe II, durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Auflaufen der Pflanzen.The method for controlling harmful fungi is carried out by the separate or combined application of compound (s) I and active ingredients) II, or a mixture of compound (s) I and at least one of the active compounds II, by spraying or dusting the seeds, the plants or soils before or after sowing the plants or before or after emergence of the plants.
Die erfindungsgemäßen fungiziden Mischungen, bzw. die Verbindung(en) I und mindestens einer der Wirkstoffe II, können in die üblichen Formulierungen übergeführt werden, z.B. Lösungen, Emulsionen, Suspensionen, Stäube, Pulver, Pasten und Granulate. Die Anwendungsform richtet sich nach dem jeweiligen Verwendungszweck; sie soll in jedem Fall eine möglichst feine und gleichmäßige Verteilung der erfindungsgemäßen Mischung gewährleisten.The fungicidal mixtures according to the invention, or the compound (s) I and at least one of the active compounds II, can be converted into the customary formulations are, for example, solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the respective purpose; It should in any case ensure the finest possible and uniform distribution of the mixture according to the invention.
Die Formulierungen werden in an sich bekannter Weise hergestellt, z.B. durch Verstrecken der Wirkstoffe 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, XyIoI), ParaffineThe formulations are prepared in a manner known per se, for example by stretching the active compounds with solvents and / or excipients, if desired using emulsifiers and dispersants. Solvents / auxiliaries which are suitable are essentially: - water, aromatic solvents (for example Solvesso ® products, xylene), paraffins
(z.B. Erdölfraktionen), Alkohole (z.B. Methanol, Butanol, Pentanol, Benzylalkohol), Ketone (z.B. Cyclohexanon, gamma-Butryolacton), Pyrrolidone (N-Methyl- pyrrolidon, N-Octylpyrrolidon), Acetate (Glykoldiacetat), Glykole, Dimethylfettsäu- reamide, Fettsäuren und Fettsäureester. Grundsätzlich können auch Lösungsmit- telgemische verwendet werden.(eg, petroleum fractions), alcohols (eg, methanol, butanol, pentanol, benzyl alcohol), ketones (eg, cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone, N-octylpyrrolidone), acetates (glycol diacetate), glycols, dimethyl fatty acid amides , Fatty acids and fatty acid esters. In principle, solvent mixtures can also be used.
- 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. Polyoxy- ethylen-Fettalkohol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Lignin-Sulfitablaugen und Methylcellulose.Excipients such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
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 des Naphthalins bzw. der Naphtalinsulfonsäure mit Phenol und Formaldehyd, Polyoxyethy- lenoctylphenolether, ethoxyliertes Isooctylphenol, Octylphenol, Nonylphenol, Alkylphe- nolpolyglykolether, Tributylphenylpolyglykolether, Tristerylphenylpolyglykolether, Alkyl- arylpolyetheralkohole, Alkohol- und Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether, ethoxyliertes Polyoxypropylen, Laurylalkoholpoly- glykoletheracetal, Sorbitester, Ligninsulfitablaugen und Methylcellulose in Betracht.The surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, tristerylphenyl polyglycol ethers, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene , Laurylalkoholpoly- glycol ether acetal, sorbitol esters, Ligninsulfitablaugen and methyl cellulose into consideration.
Zur Herstellung von direkt versprühbaren Lösungen, Emulsionen, Pasten oder Öldis- persionen kommen Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wieFor the production of directly sprayable solutions, emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as
Kerosin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Toluol, XyIoI, Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, Methanol, Ethanol, Propanol, Butanol, Cyclohexanol, Cyclohexanon, Isophoron, stark pola- re Lösungsmittel, z.B. Dimethylsulfoxid, N-Methylpyrrolidon oder Wasser in Betracht. Pulver-, Streu- und Stäubmittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit mindestens einem festen Trägerstoff hergestellt werden.Kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration. Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with at least one solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate, können durch Bindung der Wirkstoffe an mindestens einen festen Trägerstoff hergestellt werden. Feste Trägerstoffe sind z.B. Mineralerden, wie Kieselgele, Silikate, Talkum, Kaolin, Attaclay, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nussschalenmehl, Ce I Iu lose pul- ver und andere feste Trägerstoffe.Granules, e.g. Coating, impregnation and homogeneous granules can be prepared by binding the active ingredients to at least one solid carrier. Solid carriers are e.g. Mineral soils 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 cereal flour, tree bark, wood and nutshell flour, Ce I Iu loose powder and other solid carriers.
Die Formulierungen enthalten im allgemeinen 0,01 bis 95 Gew.-%, vorzugsweise 0,1 bis 90 Gew.-%, der Verbindung(en) I und mindestens einem der Wirkstoffe Il bzw. der Mischung aus Verbindung(en) I mit mindestens einem der Wirkstoffe II. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100%, (nach NMR-Spektrum) eingesetzt.The formulations generally contain from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the compound (s) I and at least one of the active compounds II or of the mixture of compound (I) I with at least one of the active ingredients II. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to 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 einer erfindungsgemäßen Mischung werden mit 90 Gew. -Teilen Wasser oder einem wasserlöslichen Lösungsmittel gelöst. Alternativ werden Netzmittel oder andere Hilfsmittel zugefügt. Bei der Verdünnung in Wasser löst sich der Wirkstoff. Man erhält auf diese Weise eine Formulierung mit einem Wirkstoffgehalt von 10 Gew.-%.10 parts by weight of a mixture according to the invention are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with an active substance content of 10% by weight.
B) Dispergierbare Konzentrate (DC)B) Dispersible Concentrates (DC)
20 Gew.-Teile einer erfindungsgemäßen Mischung werden in 70 Gew. -Teilen Cyclohe- xanon unter Zusatz von 10 Gew. -Teilen eines Dispergiermittels, z.B. Polyvinylpyrroli- don, gelöst. Bei Verdünnung in Wasser ergibt sich eine Dispersion. Der Wirkstoffgehalt beträgt 20 Gew.-%.20 parts by weight of a mixture according to the invention are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersing agent, e.g. Polyvinylpyrrolidone, dissolved. Dilution in water gives a dispersion. The active ingredient content is 20% by weight.
C) Emulgierbare Konzentrate (EC) 15 Gew.-Teile einer erfindungsgemäßen Mischung werden in 75 Gew. -Teilen XyIoI unter Zusatz von Ca-Dodecylbenzolsulfonat und Ricinusölethoxylat (jeweils 5 Gew.- Teile) gelöst. Bei der Verdünnung in Wasser ergibt sich eine Emulsion. Die Formulierung hat einen Wirkstoffgehalt von 15 Gew.-%.C) Emulsifiable Concentrates (EC) 15 parts by weight of a mixture according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion. The formulation has an active ingredient content of 15% by weight.
D) Emulsionen (EW, EO)D) Emulsions (EW, EO)
25 Gew.-Teile einer erfindungsgemäßen Mischung werden in 35 Gew. -Teilen XyIoI unter Zusatz von Ca-Dodecylbenzolsulfonat und Ricinusölethoxylat Qeweils 5 Gew.- Teile) gelöst. Diese Mischung wird mittels einer Emulgiermaschine (z.B. Ultraturrax) in 30 Gew. Teile Wasser gegeben und zu einer homogenen Emulsion gebracht. Bei der Verdünnung in Wasser ergibt sich eine Emulsion. Die Formulierung hat einen Wirkstoffgehalt von 25 Gew.-%.25 parts by weight of a mixture according to the invention are dissolved in 35 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate in each case 5% by weight. Parts) solved. This mixture is added by means of an emulsifying machine (eg Ultraturrax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion. The formulation has an active ingredient content of 25% by weight.
E) Suspensionen (SC, OD)E) suspensions (SC, OD)
20 Gew.-Teile einer erfindungsgemäßen Mischung werden unter Zusatz von 10 Gew.- Teilen Dispergier- und Netzmitteln und 70 Gew.-Teilen Wasser oder einem organischen Lösungsmittel in einer Rührwerkskugelmühle zu einer feinen Wirkstoffsuspensi- on zerkleinert. Bei der Verdünnung in Wasser ergibt sich eine stabile Suspension des Wirkstoffs. Der Wirkstoffgehalt in der Formulierung beträgt 20 Gew.-%.20 parts by weight of a mixture according to the invention are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine Wirkstoffsuspensi- on. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the formulation is 20% by weight.
F) Wasserdispergierbare und wasserlösliche Granulate (WG, SG)F) Water-dispersible and water-soluble granules (WG, SG)
50 Gew.-Teile einer erfindungsgemäßen Mischung werden unter Zusatz von 50 Gew- Teilen 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. Die Formulierung hat einen Wirkstoffgehalt von 50 Gew.- %.50 parts by weight of a mixture according to the invention are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of industrial equipment (for example 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. The formulation has an active ingredient content of 50% by weight.
G) Wasserdispergierbare und wasserlösliche Pulver (WP, SP)G) Water-dispersible and water-soluble powders (WP, SP)
75 Gew.-Teile einer erfindungsgemäßen Mischung werden unter Zusatz von 25 Gew.- Teilen Dispergier- und Netzmitteln sowie Kieselsäuregel in einer Rotor-Strator Mühle vermählen. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lö- sung des Wirkstoffs. Der Wirkstoffgehalt der Formulierung beträgt 75 Gew.-%.75 parts by weight of a mixture according to the invention are ground with the addition of 25 parts by weight of dispersants and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the formulation is 75% by weight.
2. Produkte für die Direktapplikation2. Products for direct application
H) Stäube (DP)H) dusts (DP)
5 Gew.-Teile einer erfindungsgemäßen Mischung werden fein gemahlen und mit 95 Gew.-Teilen feinteiligem Kaolin innig vermischt. Man erhält dadurch ein Stäubemittel mit einem Wirkstoffgehalt von 5 Gew.-%.5 parts by weight of a mixture according to the invention are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with an active ingredient content of 5 wt .-%.
J) Granulate (GR, FG, GG, MG)J) Granules (GR, FG, GG, MG)
0,5 Gew-Teile einer erfindungsgemäßen Mischung werden fein gemahlen und mit 99,5 Gew.-Teilen Trägerstoffe verbunden. Gängige Verfahren sind dabei die Extrusion, die Sprühtrocknung oder die Wirbelschicht. Man erhält dadurch ein Granulat für die Direktapplikation mit einem Wirkstoffgehalt von 0,5 Gew.-%.0.5 parts by weight of a mixture according to the invention are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
K) ULV- Lösungen (UL)K) ULV solutions (UL)
10 Gew.-Teile einer erfindungsgemäßen Mischung werden in 90 Gew.-Teilen eines organischen Lösungsmittel z.B. XyIoI gelöst. Dadurch erhält man ein Produkt für die Direktapplikation mit einem Wirkstoffgehalt von 10 Gew.-%.10 parts by weight of a mixture according to the invention are in 90 parts by weight of a dissolved organic solvent such as xylene. This gives a product for direct application with an active ingredient content of 10 wt .-%.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder den daraus berei- teten 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 Wirk- Stoffe gewährleisten.The active compounds can be used 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, scattering agents, granules by spraying, misting, dusting, scattering or pouring. The forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active substances.
Wässrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulver, Öldispersionen) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Sub- stanzen 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 eventuell 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, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, 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 compound concentrations in the ready-to-use preparations can be varied within wide ranges. 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 (ULV) process, it being possible to apply formulations containing 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, andere Schädlingsbekämpfungsmittel, Bakterizide, gewünschtenfalls auch erst unmittelbar vor der Anwendung (Tankmix), zugesetzt werden. Diese Mittel werden üblicherweise zu den erfindungsgemäßen Mitteln im Gewichtsverhältnis 1 :100 bis 100:1 , bevorzugt 1 :10 bis 10:1 , gemischt.To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, other pesticides, bactericides, if desired, also just immediately before use (tank mix), can be added. These agents are usually mixed to give the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
Als Adjuvants in diesem Sinne kommen insbesondere in Frage: organisch modifizierte Polysiloxane, z.B. Break Thru S 240®; Alkoholalkoxylate, z. B. Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® und Lutensol ON 30®; EO-PO-Blockpolymerisate, z. B. Pluro- nic RPE 2035® und Genapol B®; Alkoholethoxylate, z. B. Lutensol XP 80®; und Natri- umdioctylsulfosuccinat, z. B. Leophen RA®.As adjuvants in this sense are in particular: organically modified polysiloxanes, eg Break Thru S 240 ® ; Alcohol alkoxylates, eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®; EO-PO block polymers, eg. B. Pluro- nic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e. B. Leophen RA ®.
Die Verbindungen I und II, bzw. die Mischungen oder die entsprechenden Formulierungen werden angewendet, indem man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit einer fungizid wirksamen Menge der Mischung, bzw. der Verbindungen I und Il bei getrennter Ausbringung, behandelt. Die Anwendung kann vor oder nach dem Befall durch die Schadpilze erfolgen.The compounds I and II, or the mixtures or the corresponding formulations are applied by the harmful fungi, their habitat or the treated plants, seeds, soils, areas, materials or spaces with a fungicidally effective amount of the mixture, or the compounds I and II with separate application treated. The application can be made before or after the attack by the harmful fungi.
Anwendungsbeispielexample
Die fungizide Wirkung der Einzelverbindungen und der erfindungsgemäßen Mischungen ließ sich durch die folgenden Versuche zeigen.The fungicidal action of the individual compounds and of the mixtures according to the invention was demonstrated by the following experiments.
Die Wirkstoffe wurden getrennt oder gemeinsam als eine Stammlösung aufbereitet mit 25 mg Wirkstoff, welcher mit einem Gemisch aus Aceton und/oder Dimethylsulfoxid und dem Emulgator Uniperol® EL (Netzmittel mit Emulgier- und Dispergierwirkung auf der Basis ethoxylierter Alkylphenole) im Volumen-Verhältnis Lösungsmittel-Emulgator von 99 zu 1 ad 10 ml aufgefüllt wurde. Anschließend wurde ad 100 ml mit Wasser aufgefüllt. Diese Stammlösung wurde mit dem beschriebenen Lösungsmittel- Emulgator-Wasser Gemisch zu der unten angegebenen Wirkstoffkonzentration verdünnt.The active compounds were prepared separately or together as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or dimethyl sulfoxide and the emulsifier Uniperol ® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent- Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the active ingredient concentration given below.
Alternativ dazu wurden die Wirkstoffe Epoxiconazol, Triticonazol und Pyraclostrobin als handelsübliche Fertigformulierung verwendet und mit Wasser auf die angegebenen Wirkstoffkonzentrationen verdünnt.Alternatively, the active ingredients epoxiconazole, triticonazole and pyraclostrobin were used as a commercially available ready-made formulation and diluted with water to the stated active substance concentrations.
Die visuell ermittelten Werte für den Prozentanteil befallener Blattflächen wurden in Wir- kungsgrade als % der unbehandelten Kontrolle umgerechnet.The visually determined values for the percentage of affected leaf areas were converted into efficiencies as% of the untreated control.
Der Wirkungsgrad (W) wird nach der Formel von Abbot wie folgt berechnet:The efficiency (W) is calculated according to the formula of Abbot as follows:
W = (1 - α/ ß) - 100W = (1-α / β) -100
α entspricht dem Pilzbefall der behandelten Pflanzen in % und ß entspricht dem Pilzbefall der unbehandelten (Kontroll-) Pflanzen in %α corresponds to the fungal infestation of the treated plants in% and β corresponds to the fungal infestation of the untreated (control) plants 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.With an efficiency of 0, the infestation of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants have no infestation.
Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby- Formel (S. R. Colby: „Calculating synergistic and antagonistic responses of herbicide Combinations", Weeds ^5, S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen.The expected efficiencies for drug combinations were determined according to the Colby formula (S.R. Colby: "Calculating synergistic and antagonistic responses of herbicidal combinations", Weeds ^ 5, pp. 20-22, 1967) and compared with the observed efficiencies.
Colby Formel: E = x + y - x°y/100 zu erwartender Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz der Mischung aus den Wirkstoffen A und B in den Konzentrationen a und b; der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs A in der Konzentration a; der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs B in der Konzentration b.Colby formula: E = x + y - x ° y / 100 expected efficiency, expressed as% of untreated control, when using the mixture of Active Agents A and B at concentrations a and b; the efficiency, expressed in% of untreated control, when using active substance A at concentration a; the efficiency expressed as% of untreated control when using active substance B in concentration b.
Anwendungsbeispiel 1 - Wirksamkeit gegen die Netzfleckenkrankheit der Gerste verursacht durch Pyrenophora teres bei 1 Tag protektiver AnwendungApplication Example 1 - Efficacy against barley spot blight caused by Pyrenophora teres at 1 day of protective application
Blätter von in Töpfen gewachsenen Gerstenkeimlingen wurden mit wässriger Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht. 24 Stunden nach dem Antrocknen des Spritzbelages wurden die Versuchspflanzen mit einer wässrigen Sporensuspension von Pyrenophora [syn. Drechslera] teres, dem Erreger der Netzfleckenkrankheit inokuliert. Anschließend wurden die Versuchspflanzen im Gewächshaus bei Temperaturen zwischen 20 und 240C und 95 bis 100 % relativer Luftfeuchtigkeit aufgestellt. Nach 6 Tagen wurde das Ausmaß der Krankheitsentwicklung visuell in % Befall der gesamten Blattfläche ermittelt.Leaves of potted barley seedlings were sprayed to drip point with aqueous suspension in the concentration of active compound given below. 24 hours after the spray coating had dried on, the test plants were incubated with an aqueous spore suspension of Pyrenophora [syn. Drechslera] teres, the causative agent of net blotch inoculation. Subsequently, the test plants were placed in the greenhouse at temperatures between 20 and 24 0 C and 95 to 100% relative humidity. After 6 days, the extent of disease development was determined visually as% of total leaf area.
Anwendungsbeispiel 2 - Wirksamkeit gegen den Grauschimmel an Paprika blättern verursacht durch Botrytis cinerea bei 1 Tag protektiver AnwendungApplication Example 2 - Activity against gray mold on pepper leaf caused by Botrytis cinerea at 1 day of protective application
Paprikasämlinge der Sorte „Neusiedler Ideal Elite" wurden, nachdem sich 2 - 3 Blätter gut entwickelt hatten, mit einer wässrigen Suspension in der unten angegebenen Wirkstoff konzentration bis zur Tropfnässe besprüht. Am nächsten Tag wurden die behandelten Pflanzen mit einer Sporensuspension von Botrytis cinerea, die 1 ,7 x 106 Sporen/ml in einer 2%igen wässrigen Biomalzlösung enthielt, inokuliert. Anschließend wurden die Versuchspflanzen in eine Klimakammer mit 22 bis 24°C, Dunkelheit und hoher Luftfeuchtigkeit gestellt. Nach 5 Tagen konnte das Ausmaß des Pilzbefalls auf den Blättern visuell in % ermittelt werden.Paprika seedlings of the cultivar "Neusiedler Ideal Elite" were sprayed to drip point after 2-3 leaves had developed well, and the next day the treated plants were treated with a spore suspension of Botrytis cinerea, the 1 x 7 x 10 6 spores / ml in a 2% aqueous biomalt solution, and the test plants were placed in a climatic chamber at 22 to 24 ° C, in the dark and at high humidity Scrolls can be determined visually in%.
Anwendungsbeispiel 3 - Kurative Wirksamkeit gegen Weizenbraunrost verursacht durch Puccinia recondita Use Example 3 - Curative activity against wheat brown rust caused by Puccinia recondita
Blätter von in Töpfen gewachsenen Weizensämlingen der Sorte "Kanzler" wurden mit einer Sporensuspension des Braunrostes (Puccinia recondita) inokuliert. Danach wurden die Töpfe für 24 Stunden in eine Kammer mit hoher Luftfeuchtigkeit (90 bis 95 %) und 20 bis 220C gestellt. Während dieser Zeit keimten die Sporen aus und die Keimschläuche drangen in das Blattgewebe ein. Die infizierten Pflanzen wurden am nächsten Tag mit der oben beschriebenen Wirkstofflösung in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht. Nach dem Antrocknen des Spritzbelages wurden die Versuchspflanzen im Gewächshaus bei Temperaturen zwischen 20 und 220C und 65 bis 70 % relativer Luftfeuchte für 7 Tage kultiviert. Dann wurde das Ausmaß der Rostpilzentwicklung auf den Blättern ermittelt.Leaves of potted wheat seedlings of the variety "Chancellor" were inoculated with a spore suspension of the brown rust (Puccinia recondita). Thereafter, the pots were placed in a high humidity chamber (90 to 95%) and 20 for 24 hours to 22 0 C provided. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue. The infected plants were sprayed the next day with the above-described active ingredient solution in the drug concentration indicated below to drip point. After the spray coating had dried on, the test plants were cultivated in the greenhouse at temperatures between 20 and 22 ° C. and 65 to 70% relative atmospheric humidity for 7 days. Then the extent of rust fungus development on the leaves was determined.
Anwendungsbeispiel 4 - Protektive Wirksamkeit gegen Puccinia recondita an Weizen (Weizen brau nrost) Use Example 4 - Protective activity against Puccinia recondita on wheat (wheat brewing)
Blätter von in Töpfen gewachsenen Weizensämlingen der Sorte "Kanzler" wurden mit einer wässriger Suspension in der unten angegebenen Wirkstoffkonzentration bis zur Tropfnässe besprüht. Am nächsten Tag wurden die behandelten Pflanzen mit einerLeaves of potted wheat seedlings of the variety "Chancellor" were sprayed to drip point with an aqueous suspension in the active ingredient concentration given below. The next day, the treated plants were treated with a
Sporensuspension des Weizenbraunrostes (Puccinia recondita) inokuliert. Anschließend wurden die Pflanzen für 24 Stunden in eine Kammer mit hoher Luftfeuchtigkeit (90 bis 95 %) bei 20 bis 220C gestellt. Während dieser Zeit keimten die Sporen aus und die Keimschläuche drangen in das Blattgewebe ein. Am folgenden Tag wurden die Versuchspflanzen ins Gewächshaus zurückgestellt und bei Temperaturen zwischen 20 und 220C und 65 bis 70 % relativer Luftfeuchte für weitere 7 Tage kultiviert. Dann wurde das Ausmaß der Rostpilzentwicklung auf den Blättern visuell ermittelt.Spore suspension of wheat brown rust (Puccinia recondita) inoculated. Subsequently, the plants were placed in a high humidity chamber (90 to 95%) at 20 to 22 ° C. for 24 hours. During this time, the spores germinated and the germ tubes penetrated into the leaf tissue. The following day, the test plants were returned to the greenhouse and cultured at temperatures between 20 and 22 0 C and 65 to 70% relative humidity for a further 7 days. Then the extent of rust fungus development on the leaves was visually determined.
Anwendungsbeispiel 5 -Aktivität gegen den Verursacher der Krautfäule Phythophthora infestans im Mikrotitter-Test Use Example 5 Activity against the causative agent of the late blight Phythophthora infestans in the microtiter test
Für diesen Test wurden die Wirkstoffe getrennt als Stammlösung formuliert mit einer Konzentration von 10000 ppm in Dimethylsulfoxid. Der Wirkstoff Triticonazol wurde als handelsübliche Formulierung verwendet und mit Wasser auf die angegebene Konzentration verdünnt.For this test, the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in dimethylsulfoxide. The active ingredient triticonazole was used as a commercial formulation and diluted with water to the specified concentration.
Die Stammlösung wurde in eine Mikrotitterplatte (MTP) pipettiert und mit einem wäss- rigen Pilznährmedium auf Erbsensaftbasis auf die angegebene Wirkstoffkonzentration verdünnt. Anschließend erfolgte die Zugabe einer wässrigen Zoosporensuspension von Phytophthora infestans. Die Platten wurden in einer wasserdampf-gesättigten Kammer bei Temperaturen von 18°C aufgestellt. Mit einem Absorbtionsphotometer wurden die MTPn am 7. Tag nach der Inokulation bei 405 nm gemessen.The stock solution was pipetted into a microtiter plate (MTP) and diluted with an aqueous fungus nutrient medium based on pea juice to the stated active substance concentration. This was followed by the addition of an aqueous zoospore suspension of Phytophthora infestans. The plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. Using an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.
Die gemessenen Parameter wurden mit dem Wachstum der wirkstofffreien Kontrollvariante und dem pilz- und wirkstofffreien Leerwert verrechnet, um das relative Wachstum in % der Pathogene in den einzelnen Wirkstoffen zu ermitteln.The measured parameters were compared with the growth of the drug-free control variant and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.

Claims

Patentansprüche claims
1. Fungizide Mischungen zur Bekämpfung von pflanzenpathogenen Schadpilzen, enthaltend 1) mindestens ein i-Methylpyrazol-4-ylcarbonsäureanilid der Formel I1. Fungicidal mixtures for controlling phytopathogenic harmful fungi, comprising 1) at least one i-methylpyrazol-4-ylcarbonsäureanilid of formula I.
in der X für Sauerstoff oder Schwefel, R1 für Ci-C4-AIkVl oder Ci-C4- Halogenalkyl und R2 für Wasserstoff oder Halogen stehen, und are haloalkyl and R 2 is hydrogen or halogen, and - in which X is oxygen or sulfur, R 1 is Ci-C 4 -alkyl or Ci-C 4
2) mindestens einen Wirkstoff II, ausgewählt aus den Wirkstoffgruppen A) bis L):2) at least one active ingredient II selected from the active ingredient groups A) to L):
A) Azole, ausgewählt aus Bitertanol, Bromuconazol, Cyproconazol, Difeno- conazol, Diniconazol, Enilconazol, Epoxiconazol, Fluquinconazol, Fenbu- conazol, Flusilazol, Flutriafol, Hexaconazol, Imibenconazol, Ipconazol,A) Azoles selected from bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbiconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole,
Metconazol, Myclobutanil, Penconazol, Propiconazol, Prothioconazol, Simeconazol, Triadimefon, Triadimenol, Tebuconazol, Tetraconazol, Triticonazol, Prochloraz, Pefurazoate, Imazalil, Triflumizol, Cyazofamid, Benomyl, Carbendazim, Thiabendazol, Fuberidazol, Ethaboxam, Etri- diazol und Hymexazol;Metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamide, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole and hymexazole;
B) Strobilurine, ausgewählt aus Azoxystrobin, Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methominostrobin, Orysastrobin, Pic- oxystrobin, Pyraclostrobin, Trifloxystrobin, Enestroburin, (2-Chlor-5-[1-(3- methyl-benzyloxyimino)-ethyl]-benzyl)-carbaminsäure-methylester,B) Strobilurins selected from azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) - ethyl] benzyl) -carbamic acid methylester,
(2-Chlor-5-[1-(6-methyl-pyridin-2-ylmethoxyimino)-ethyl]-benzyl)-carb- aminsäuremethylester und 2-(ortho-(2,5-Dimethyl-phenyl-oxymethylen)- phenyl)-3-methoxy-acrylsäuremethylester;(2-Chloro-5- [1- (6-methyl-pyridin-2-ylmethoxyimino) -ethyl] -benzyl) -carbamic acid methyl ester and 2- (ortho (2,5-dimethyl-phenyl-oxymethylene) -phenyl ) -3-methoxy-methyl acrylate;
C) Carbonsäureamide, ausgewählt aus Carboxin, Benalaxyl, Boscalid,C) Carboxylic acid amides selected from carboxin, benalaxyl, boscalid,
Fen-hexamid, Flutolanil, Furametpyr, Mepronil, Metalaxyl, Mefenoxam, Ofurace, Oxadixyl, Oxycarboxin, Penthiopyrad, Thifluzamid, Tiadinil, 3,4- Di-chlor-N-(2-cyanophenyl)-isothiazol-5-carbonsäureamid, Dimethomorph, Flumorph, Flumetover, Fluopicolid (Picobenzamid), Zoxamid, Carpropa- mid, Diclocymet, Mandipropamid, N-(2-(4-[3-(4-Chlor-phenyl)-prop-2- ynyloxy]-3-methoxy-phenyl)-ethyl)-2-methansulfonylamino-3-methyl- butyramid, N-(2-(4-[3-(4-Chlor-phenyl)-prop-2-ynyloxy]-3-methoxy-phenyl)- ethyl)-2-ethansulfonylamino-3-methyl-butyrannicl, 3-(4-Chlor-phenyl)-3-(2- isopropoxy-carbonylamino-3-methyl-butyrylamino)-propion-säure- metHex-hexamide, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxine, penthiopyrad, thifluzamide, tiadinil, 3,4-di-chloro-N- (2-cyanophenyl) -isothiazole-5-carboxylic acid amide, dimethomorph, Flumorphic, flumetover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet, mandipropamide, N- (2- [4- [3- (4-chloro-phenyl) -prop-2-] ynyloxy] -3-methoxy-phenyl) -ethyl) -2-methanesulfonylamino-3-methyl-butyramide, N- (2- [4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3 -methoxy-phenyl) -ethyl) -2-ethanesulfonylamino-3-methyl-butyrannicl, 3- (4-chloro-phenyl) -3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino) -propionic acid met
in der R4 Methyl oder Ethyl bedeutet, in which R 4 is methyl or ethyl,
4-Difluormethyl-2-methyl-thiazol-5-carbonsäure-N-(4'-brom-biphenyl-2-yl)- amid, 4-Difluormethyl-2-methyl-thiazol-5-carbonsäure-N-(4'-trifluormethyl- biphenyl-2-yl)-amid, 4-Difluormethyl-2-methyl-thiazol-5-carbonsäure-N-(4'- chlor-3'-fluor-biphenyl-2-yl)-amid, 3-Difluormethyl-1-methyl-pyrazol-4- carbonsäure-(3',4'-dichlor-4-fluor-biphenyl-2-yl)-amid und 3,4-Dichlor- isothiazol-5-carbonsäure-N-(2-cyano-phenyl)-amid;4-Difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-bromo-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4 ' -trifluoromethyl-biphenyl-2-yl) -amide, 4-difluoromethyl-2-methyl-thiazole-5-carboxylic acid N- (4'-chloro-3'-fluorobiphenyl-2-yl) -amide, 3 Difluoromethyl-1-methyl-pyrazole-4-carboxylic acid (3 ', 4'-dichloro-4-fluoro-biphenyl-2-yl) -amide and 3,4-dichloro-isothiazole-5-carboxylic acid N- (2 -cyano-phenyl) -amide;
Heterocyclische Verbindungen, ausgewählt aus Fluazinam,Heterocyclic compounds selected from fluazinam,
Pyrifenox, Bupirimat, Cyprodinil, Fenarimol, Ferimzon, Mepanipyrim, Nua- rimol, Pyrimethanil, Triforin, Fenpiclonil, Fludioxonil, Aldimorph, Dode- morph, Fenpropimorph, Tridemorph, Fenpropidin, Iprodion, Procymidon, Vinclozolin, Famoxadon, Fenamidon, Octhilinon, Probenazol, 5-Chlor-7- (4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluor-phenyl)-[1 ,2,4]triazolo[1 ,5- ajpyrimidin, Anilazin, Diclomezin, Pyroquilon, Proquinazid, Tricyclazol, die Verbindung der Formel IV (2-Butoxy-6-iodo-3-propyl-chromen-4-on)Pyrifenox, Bupirimat, Cyprodinil, Fenarimol, Ferimzone, Mepanipyrim, Nuarimbol, Pyrimethanil, Triforin, Fenpiclonil, Fludioxonil, Aldimorph, Dodemorph, Fenpropimorph, Tridemorph, Fenpropidin, Iprodione, Procymidone, Vinclozolin, Famoxadone, Fenamidon, Octhilinone, Probenazole, 5-Chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-ajpyrimidine, anilazine, diclomethine , Pyroquilone, proquinazide, tricyclazole, the compound of formula IV (2-butoxy-6-iodo-3-propyl-chromen-4-one)
Acibenzolar-S-methyl, Captafol, Captan, Dazomet, Folpet, Fenoxanil, Qui- noxyfen und 3-(3-Brom-6-fluor-2-methyl-indol-1-sulfonyl)-[1 ,2,4]triazol-1- sulfonsäureAcibenzolar-S-methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen and 3- (3-bromo-6-fluoro-2-methyl-indole-1-sulfonyl) - [1, 2,4] triazole -1- sulfonic acid
V;V;
E) Carbamate, ausgewählt aus Mancozeb, Maneb, Metam, Metiram, Ferbam, Propineb, Thiram, Zineb, Ziram, Diethofencarb, Iprovalicarb, Flubenthiavalicarb, Propamocarb, N-(1 -(1 -(4-cyanophenyl)ethansulfonyl)- but-2-yl)carbaminsäure-(4-fluorphenyl)ester, 3-(4-Chlor-phenyl)-3-(2-iso- propoxycarbonylamino-3-methyl-butyrylannino)-propionsäure-nnethylester der Formel VI E) Carbamates selected from Mancozeb, Maneb, Metam, Metiram, Ferbam, Propineb, Thiram, Zineb, Ziram, Diethofencarb, Iprovalicarb, Flubenthiavalicarb, Propamocarb, N- (1- (1 - (4-cyanophenyl) ethanesulfonyl) - but- 2-yl) -carbamic acid (4-fluorophenyl) esters, 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methyl-butyrylannino) -propionic acid-n-ethyl ester of the formula VI
und Carbamatoximether der Formel VII and carbamato oxime ethers of formula VII
in der Z für N oder CH steht; Z is N or CH;
F) Sonstige Fungizide, ausgewählt ausF) Other fungicides selected from
Guanidin, Dodin, Iminoctadin, Guazatin,Guanidine, dodin, iminoctadine, guazatine,
Antibiotika: Kasugamycin, Streptomycin, Polyoxin, Validamycin A, Nitrophenylderivate: Binapacryl, Dinocap, Dinobuton,Antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobuton,
Schwefelhaltige Heterocyclylverbindungen: Dithianon, Isoprothiolan,Sulfur-containing heterocyclyl compounds: dithianone, isoprothiolane,
Organometallverbindungen: Fentin-Salze,Organometallic compounds: Fentin salts,
Organophosphorverbindungen: Edifenphos, Iprobenfos, Fosetyl,Organophosphorus Compounds: Edifenphos, Iprobenfos, Fosetyl,
Fosetyl-Aluminium, Phosphorige Säure und ihre Salze, Pyrazophos, ToIc- lofos-methyl,Fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolcofos-methyl,
Organochlorverbindungen: Chlorthalonil, Dichlofluanid, Flusulfamid, He- xachlorbenzol, Phthalid, Pencycuron, Quintozen, Thiophanat-Methyl, To- lylfluanid,Organochlorine compounds: chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, toluylfluanid,
Anorganische Wirkstoffe: Bordeaux Brühe, Kupferacetat, Kupferhydroxid, Kupferoxychlorid, basisches Kupfersulfat, Schwefel,Inorganic active ingredients: Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur,
Sonstige: Cyflufenamid, Cymoxanil, Dimethirimol, Ethirimol,Other: Cyflufenamid, Cymoxanil, Dimethirimol, Ethirimol,
Furalaxyl, Metrafenon und Spiroxamin;Furalaxyl, Metrafenone and Spiroxamine;
in einer synergistisch wirksamen Menge.in a synergistically effective amount.
2. Fungizide Mischungen nach Anspruch 1, enthaltend als Komponente 1)2. Fungicidal mixtures according to claim 1, containing as component 1)
1-Methyl-3-trifluormethyl-1 H-pyrazol-4-carbonsäure-N-(4'-trifluormethyl-biphen-2- yl)-amid, 3-Difluormethyl-1 -methyl-1 H-pyrazol-4-carbonsäure-N-(4'-trifluormethyl- biphen-2-yl)-amid, 1 -Methyl-3-trifluormethyl-5-fluor-1 H-pyrazol-4-carbonsäure-N- (4'-trifluormethylbiphenyl-2-yl)-amid, 1 ,3-Dimethyl-5-chlor-1 H-pyrazol-4- carbonsäure-N-(4'-trifluornnethylbiphenyl-2-yl)-annid, 1 ,3-Dimethyl-1 H-pyrazol-4- carbonsäure-N-(4'-trifluornnethylbiphenyl-2-yl)-annid, 1 -Methyl-3-fluormethyl-1 H- pyrazol-4-carbonsäure-N-(4'-trifluomnethylbiphenyl-2-yl)-amid, 1 -Methyl-3- chlordifluormethyl-1 H-pyrazol-4-carbonsäure-N-(4'-trifluornnethylbiphenyl-2-yl)- amid oder 1-Methyl-3-chlorfluormethyl-1 H-pyrazol-4-carbonsäure-N-(4'- trifluormethylbiphenyl-2-yl)-amid.1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphen-2-yl) -amide, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethylbiphen-2-yl) -amide, 1-methyl-3-trifluoromethyl-5-fluoro-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide, 1, 3-dimethyl-5-chloro-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -annide, 1, 3 -Dimethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -annide, 1-methyl-3-fluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'- trifluoromethyl-biphenyl-2-yl) -amide, 1-methyl-3-chlorodifluoromethyl-1H-pyrazole-4-carboxylic acid N- (4'-trifluoromethyl-biphenyl-2-yl) -amide or 1-methyl-3-chlorofluoromethyl-1 H-pyrazole-4-carboxylic acid N- (4'-trifluoromethylbiphenyl-2-yl) -amide.
3. Fungizide Mischungen gemäß Anspruch 1 oder 2, enthaltend die Komponenten 1) und 2) in einem Gewichtsverhältnis von 100:1 bis 1 :100.3. Fungicidal mixtures according to claim 1 or 2, comprising the components 1) and 2) in a weight ratio of 100: 1 to 1: 100.
4. Mittel, enthaltend mindestens einen flüssigen oder festen Trägerstoff und eine fun- gizide Mischung gemäß Anspruch 1 oder 2.4. agent containing at least one liquid or solid carrier and a fungicidal mixture according to claim 1 or 2.
5. Verfahren zur Bekämpfung von pflanzenpathogenen Schadpilzen, dadurch gekennzeichnet, dass man die Schadpilze, deren Lebensraum oder die vor Pilzbefall zu schützenden Pflanzen, den Boden, Saatgüter, Flächen, Materialien oder Räume mit einer wirksamen Menge mindestens einer Verbindung I und mindestens einer Verbindung Il gemäß Anspruch 1 oder 2 behandelt.5. A method for controlling phytopathogenic harmful fungi, characterized in that the harmful fungi, their habitat or the plants to be protected against fungal attack, the soil, seeds, areas, materials or spaces with an effective amount of at least one compound I and at least one compound II treated according to claim 1 or 2.
6. Verfahren nach Anspruch 5, dadurch gekennzeichnet, dass man die Komponenten 1) und 2) gemäß Anspruch 1 oder 2 gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander ausbringt.6. The method according to claim 5, characterized in that the components 1) and 2) according to claim 1 or 2 at the same time, and jointly or separately, or successively auszustingt.
7. Verfahren nach Anspruch 5 oder 6, dadurch gekennzeichnet, dass man die7. The method according to claim 5 or 6, characterized in that the
Komponenten 1) und 2) gemäß Anspruch 1 oder 2 in einer Menge von 5 g/ha bis 2000 g/ha aufwendet.Components 1) and 2) according to claim 1 or 2 in an amount of 5 g / ha to 2000 g / ha expended.
8. Verfahren nach Anspruch 5 oder 6, dadurch gekennzeichnet, dass man die Komponenten 1) und 2) gemäß Anspruch 1 oder 2 in einer Menge von 1 g bis8. The method according to claim 5 or 6, characterized in that the components 1) and 2) according to claim 1 or 2 in an amount of 1 g to
1000 g pro 100 kg Saatgut anwendet.1000 g per 100 kg seed applies.
9. Saatgut, enthaltend die Mischung gemäß Anspruch 1 oder 2 in einer Menge von 1 g bis 1000 g pro 100 kg Saatgut.9. seed, containing the mixture according to claim 1 or 2 in an amount of 1 g to 1000 g per 100 kg of seed.
10. Verwendung der Verbindungen I und Il gemäß Anspruch 1 oder 2 zur Herstellung eines zur Bekämpfung von Schadpilzen geeigneten Mittels. 10. Use of the compounds I and II according to claim 1 or 2 for the preparation of a suitable agent for controlling harmful fungi.
EP06777561A 2005-07-06 2006-07-04 Fungicidal mixtures made from 1-methylpyrazol-4-ylcarboxanilides Withdrawn EP1903868A1 (en)

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