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EP1901609A2 - Fungizide mischungen auf der basis von 3-monosubstituierten pyrazolcarbonsäurebiphenylamiden - Google Patents

Fungizide mischungen auf der basis von 3-monosubstituierten pyrazolcarbonsäurebiphenylamiden

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Publication number
EP1901609A2
EP1901609A2 EP06764001A EP06764001A EP1901609A2 EP 1901609 A2 EP1901609 A2 EP 1901609A2 EP 06764001 A EP06764001 A EP 06764001A EP 06764001 A EP06764001 A EP 06764001A EP 1901609 A2 EP1901609 A2 EP 1901609A2
Authority
EP
European Patent Office
Prior art keywords
methyl
carboxylic acid
amide
pyrazole
sub
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Withdrawn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
EP06764001A
Other languages
German (de)
English (en)
French (fr)
Inventor
Jochen Dietz
Markus Gewehr
Siegfried Strathmann
Reinhard Stierl
Frank Werner
Maria Scherrer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP06764001A priority Critical patent/EP1901609A2/de
Publication of EP1901609A2 publication Critical patent/EP1901609A2/de
Withdrawn legal-status Critical Current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
  • X is oxygen or sulfur
  • R 1 is cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, difluoromethylthio or trifluoromethylthio;
  • R 2 is halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl
  • R 3 is hydrogen or halogen
  • Myclobutanil penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamide, benomyl, carbendazim, thiadendazole, fuberidazole, ethaboxam, etridiazole and hymexazole;
  • R 4 is methyl or ethyl
  • Z is N or CH
  • fungicides selected from guanidines: dodin, iminoctadine, guazatine, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A,
  • Nitrophenyl derivatives binapacryl, dinocap, dinobuton, sulfur-containing heterocyclyl compounds: dithianone, isoprothiolane, organometallic compounds: fentin salts such as fentin acetate, organophosphorus compounds: edifenphos, Iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos,
  • Organochlorine Compounds Chlorothalonil, Dichlofluanid, Flusulfamide, Hexachlorobenzene, Phthalide, Pencycuron, Quintozen, Thiophanate-Methyl, Tolylfluanid, Inorganic Substances: Bordeaux Broth, Copper Acetate, Copper Hydroxide,
  • the invention relates to a method for controlling harmful fungi with the mixture of at least one compound I and at least one of the active compounds II, the use of the compounds I and II for the preparation of such mixtures and agents and seeds containing these mixtures.
  • Substituted biphenylamides of the formula I are known from EP-A 589 301, in which a process for their preparation and a list of possible mixing partners from the series of fungicides, bactericides, acaricides, nematicides or insecticides is given.
  • WO 01/42223 likewise discloses substituted biphenylamides which are monosubstituted on the phenyl ring.
  • pyrazolecarboxamides differ from the present compounds I in particular by the substitution pattern on the biphenyl radical.
  • the active compounds II mentioned above as component 2), their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.
  • Benalaxyl methyl N- (phenylacetyl) -N- (2,6-xylyl) -DL-alaninate (DE 29 03 612); Metalaxyl, methyl N- (methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate (GB 15 00 581);
  • alkyl also includes octyl, decyl, tetradecyl and
  • Dodemorph 4-cyclododecyl-2,6-dimethylmorpholine (DE-A 1198125); Fenpropimorph, (RS) -cis-4- [3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (DE-A 27 52 096);
  • Spiroxamine (8-tert-butyl-1,4-dioxaspiro [4.5] dec-2-yl) diethylamine (EP-A 281 842);
  • Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE-A 11 64 152);
  • Mepanipyrim (4-methyl-6-prop-1-ynyl-pyrimidin-2-yl) -phenylamine (EP-A 224 339); Cyprodinil, (4-cyclopropyl-6-methylpyrimidin-2-yl) -phenylamine (EP-A 310550);
  • 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); Diniconazole, ( ⁇ E) - ⁇ - [(2,4-dichlorophenyl) methylene] - ⁇ - (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol (Noyaku Kagaku, 1983, Vol 8, p. 575);
  • Ipconazole 2 - [(4-chlorophenyl) methyl] -5- (1-methylethyl) -1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (EP-A 267,778); Metconazole, 5- (4-chlorobenzyl) -2,2-dimethyl-1 - [1, 2,4] triazole-1-ylmethylcyclopentanol
  • Penconazole 1- [2- (2,4-dichlorophenyl) pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12th Edition 2000, p. 712);
  • Tetraconazole 1 - [2- (2,4-dichlorophenyl) -3- (1,1,2,2-tetrafluoroethoxy) propyl] -1H-1, 2,4-triazole (EP-A 234 242);
  • Triflumizole (4-chloro-2-trifluoromethylphenyl) - (2-propoxy-1 - [1, 2,4] triazole-1-yl-ethylidene) -amine (JP-A 79/119 462);
  • Metiram zinc ammonium ethylenebis (dithiocarbamate) (US 3,248,400); Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);
  • 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-carboxamide (US 3,249,499);
  • 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-thione (Bull. Soc. Chim. Fr. Vol. 15, p. 891
  • 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.
  • Tricyclazole 5-methyl-1,2,4-triazolo [3,4-b] [1,3] benzothiazole [CAS RN 41814-78-2];
  • Nitrothal isopropyl, diisopropyl 5-nitroisophthalate Proc. Br. Insectic. Fungic. Conf.
  • Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
  • Fosetyl Fosetyl Aluminum, Ethyl Phosphonate (FR 22 54 276); Iprovalicarb, [(1S) -2-methyl-1- (1-p-tolyl-ethylcarbamoyl) -propyl] -carbamic acid isopropyl ester (EP-A 472 996);
  • Penthiopyrad (RS) -N- [2- (1, 3-dimethylbutyl) -3-thienyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (JP 10/130268);
  • 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-m-tolyl) -ethylidenanninooxy] -o-tolyl ⁇ -acetic acid methyl ester (EP-A 460 575);
  • the present invention was based on mixtures which show an improved action against harmful fungi, in particular for certain indications, with a reduced total amount of applied 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.
  • 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 ⁇ -alkyl is a Ci-C 4 -alkyl radical as mentioned above, or for n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2- Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, preferably a C 1 -C 4 -alky
  • 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
  • d-Ce-haloalkyl is a partially or completely halogenated C 1 -C 6 -alkyl radical, where the halogen atom (s) is / are in particular fluorine, chlorine and / or bromine, ie for a C 1 -C 4 -haloalkyl radical as mentioned above, or for 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, 5,5,5-trichloropentyl, undeca-fluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, 6,6,6 -Trichlorhexyl or Dodecafluorhexyl, preferably 4 haloalkyl group for a C-C.
  • 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).
  • 3-monosubstituted pyrazolecarboxylic acid biphenylamides I are those in which X is oxygen.
  • those compounds I are preferred in which X is sulfur.
  • R 1 is fluorine, chlorine, cyano, methyl, methoxy or trifluoromethyl
  • R 2 is fluorine, chlorine, methyl or halomethyl
  • R 3 is hydrogen or halogen.
  • R 1 is fluorine, chlorine, cyano or methoxy and R 2 is fluorine, chlorine, methyl, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl and R 3 is hydrogen, fluorine or chlorine stands.
  • R 1 is fluorine or chlorine
  • R 2 is methyl, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl
  • R 3 is hydrogen
  • Very particularly preferred compounds of the formula I are 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (3'-fluorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl-1H - pyrazole-4-carboxylic acid N- (3'-chlorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (3'-trifluoromethylbiphenyl-2-yl ) -amide, 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (3'-cyanobiphenyl-2-yl) -amide, 1-methyl-3-difluoromethyl-1H pyrazole-4-carboxylic acid N- (3'-fluorobiphenyl-2-yl) -amide, 1-methyl-3-difluoro-methyl-1H-pyrazole-4-carboxylic acid N- (3'
  • mixtures of a compound of the formula I with at least one active compound selected from the group of the 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.
  • active compound selected from the group of A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propi
  • active compound selected from the group consisting of a) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimef
  • 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 consisting of d) heterocyclic compounds selected from pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozoline, 5-chloro-7- (4-methyl -piperidin-1-yl) -6- (2,4,6-trifluoropheny
  • 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, maize and sugarcane 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 one after the other, the sequence in the case of separate application generally having no effect on the success of the treatment.
  • 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- (3'-fluorobiphenyl-2-yl) -amide, 1-methyl 3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (3'-chlorobiphenyl-2-yl) -amide, 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid N- (3 '- fluorobiphenyl-2-yl) -amide or 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid N- (3'-chlorobiphenyl-2-yl) -amide, an azole from the group A) , in particular epoxiconazole, Metconazole, triticonazole or fluquinconazole, and an insecticide, in particular fipronil and neonicotinoids such as acet
  • 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.
  • 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 compounds II are correspondingly generally 1 to 2000 g / ha, preferably 10 to 1500 g / ha, in particular 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 at least one of the active compounds II, or a mixture of compound (s) I and at least one of the active ingredients 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 synergistic mixtures according to the invention, or the compounds I and at least one of the active compounds II can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes or 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, e.g. by stretching the active compounds with solvents and / or carriers, if desired using emulsifiers and dispersants.
  • Suitable solvents / auxiliaries are essentially:
  • solvents for example Solvesso ® products, xylene
  • paraffins for example mineral oil fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma-Butryolacton
  • pyrrolidones N-methylpyrrolidone, N Octylpyrrolidone
  • acetates glycols
  • dimethyl fatty acid amides for 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.
  • Suitable surface-active substances are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and its derivatives 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, tristeryl
  • emulsions, pastes or oil dispersions come mineral oil fractions of medium to high boiling point, such as 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, strongly polar solvents, for example dimethylsulfoxide, 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.
  • Granules e.g. Coated, impregnated or homogeneous granules may be prepared by binding the active ingredients to at least one solid carrier.
  • Solid carriers are e.g. Mineral earths such as silica gels, silicates, talc, kaolin, ataclay, 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, cellulose powder or other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, ataclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such
  • 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 or HPLC spectrum).
  • formulations are: 1. Products for dilution in water
  • DC Dispersible Concentrates 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.
  • a dispersing agent e.g. Polyvinylpyrrolidone
  • a mixture according to the invention 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.
  • 25 parts by weight of a mixture according to the invention are in 35 parts by weight XyIoI with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • 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 of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and Water-soluble Granules 50 parts by weight of a mixture according to the invention are finely ground with the addition of 50 parts by weight dispersing and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules produced. 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 organic solvents, eg xylene, dissolved. This gives a product for direct application with an active ingredient content of 10 wt .-%.
  • a organic solvents eg xylene
  • 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 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 admixed to the mixtures 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 drug concentration given below.
  • 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 had no infestation.
  • Paprika seedlings of the cultivar "Neusiedler Ideal Elite” were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below, after 2-3 leaves had developed well.
  • the treated plants were inoculated with a spore suspension of Botrytis cinerea containing 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution.
  • the test plants were placed in a climatic chamber with 22 to 24 0 C, darkness and high air humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.
  • the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in dimethylsulfoxide.
  • the stock solution was mixed according to the ratio, pipetted into a microtiter plate (MTP) and diluted with an aqueous malt-based fungal nutrient medium to the stated active substance concentration. This was followed by the addition of an aqueous spore suspension of Septoria tritici.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C.
  • the absorbance photometer was used to measure the MTPs at 405 nm on the 7th day after inoculation.
  • the measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus-free and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • the active ingredients were formulated separately as stock solution with a concentration of 10,000 ppm in dimethylsulfoxide.
  • the stock solutions were mixed according to the ratio, pipetted into a microtiter plate (MTP) and diluted to the stated active compound concentration with an aqueous malt-based fungal nutrient medium. This was followed by the addition of an aqueous spore suspension of Pyricularia oryzae.
  • MTP microtiter plate
  • the plates were placed in a water vapor saturated chamber at temperatures of 18 ° C. With an absorbance photometer, the MTPs were measured at 405 nm on the 7th day after inoculation.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP06764001A 2005-07-05 2006-06-30 Fungizide mischungen auf der basis von 3-monosubstituierten pyrazolcarbonsäurebiphenylamiden Withdrawn EP1901609A2 (de)

Priority Applications (1)

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EP06764001A EP1901609A2 (de) 2005-07-05 2006-06-30 Fungizide mischungen auf der basis von 3-monosubstituierten pyrazolcarbonsäurebiphenylamiden

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DE102005031668 2005-07-05
EP06002393 2006-02-06
PCT/EP2006/063752 WO2007003603A2 (de) 2005-07-05 2006-06-30 Fungizide mischungen auf der basis von 3-monosubstituierten pyrazolcarbonsäurebiphenylamiden
EP06764001A EP1901609A2 (de) 2005-07-05 2006-06-30 Fungizide mischungen auf der basis von 3-monosubstituierten pyrazolcarbonsäurebiphenylamiden

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AR (1) AR056413A1 (es)
BR (1) BRPI0612726A2 (es)
GT (1) GT200600294A (es)
PE (1) PE20070423A1 (es)
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RS53673B1 (sr) 2005-08-05 2015-04-30 Basf Se Fungicidne smeše koje sadrže supstituisane anilide 1-metil-pirazol-4-il karboksilne kiseline
EP2001299A2 (de) * 2006-03-24 2008-12-17 Bayer CropScience Aktiengesellschaft Fungizide wirkstoffkombinationen
CA2649925A1 (en) * 2006-05-03 2007-11-15 Basf Se Use of arylcarboxylic acid biphenylamides for seed treatment
WO2008053044A2 (de) * 2006-11-03 2008-05-08 Basf Se Hetarylcarbonsäure-n-(biphen-2-yl)amid-verbindungen
CN101631465A (zh) * 2007-02-05 2010-01-20 巴斯夫欧洲公司 包含取代的1-甲基吡唑-4-基甲酰苯胺的杀真菌混合物
CN102015653B (zh) 2008-05-02 2013-09-11 巴斯夫欧洲公司 制备卤素取代的2-(氨基亚甲基)-3-氧代丁酸酯的方法
WO2009133178A1 (de) 2008-05-02 2009-11-05 Basf Se Verfahren zur herstellung von 2-(aminomethyliden)-4,4-difluor-3-oxobuttersäureestern
ES2525807T3 (es) 2008-05-05 2014-12-30 Basf Se Procedimiento de preparación de compuestos de pirazol sustituidos en las posiciones 1, 3, 4
ATE555098T1 (de) 2008-07-21 2012-05-15 Basf Se Verfahren zur herstellung 1,3-disubstituierter pyrazolcarbonsäureester
BR112012010486A2 (pt) 2009-11-05 2016-03-15 Basf Se processo para preparação de compostos 1-3 pirazol, processo para preparação de um acido pirazolcarboxilico da formula ia e processo para preparação de um composto da formula v
CN102596911B (zh) 2009-11-05 2015-04-08 巴斯夫欧洲公司 制备缩醛胺的方法及其在制备1,3-二取代的吡唑化合物中的用途
WO2012016972A2 (en) * 2010-08-05 2012-02-09 Bayer Cropscience Ag Active compound combinations
EP3178813A1 (en) 2015-12-09 2017-06-14 Basf Se Method for preparing halogenated 3-oxocarboxylates carrying a 2-alkoxymethylidene or a 2-dialkylaminomethylidene group

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JP2009501159A (ja) 2009-01-15
WO2007003603A2 (de) 2007-01-11
US20090233795A1 (en) 2009-09-17
PE20070423A1 (es) 2007-04-24
BRPI0612726A2 (pt) 2016-11-29
WO2007003603A3 (de) 2007-11-08
TW200740372A (en) 2007-11-01
UY29652A1 (es) 2007-01-31
GT200600294A (es) 2007-01-23

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