EP1903867A1 - Melanges fongicides a base de biphenylamides d'acide pyrazolcarboxylique 3,5-disubstitues - Google Patents

Melanges fongicides a base de biphenylamides d'acide pyrazolcarboxylique 3,5-disubstitues

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Publication number
EP1903867A1
EP1903867A1 EP06763960A EP06763960A EP1903867A1 EP 1903867 A1 EP1903867 A1 EP 1903867A1 EP 06763960 A EP06763960 A EP 06763960A EP 06763960 A EP06763960 A EP 06763960A EP 1903867 A1 EP1903867 A1 EP 1903867A1
Authority
EP
European Patent Office
Prior art keywords
methyl
carboxylic acid
amide
pyrazole
chloro
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Withdrawn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
EP06763960A
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German (de)
English (en)
Inventor
Jochen Dietz
Markus Gewehr
Siegfried Strathmann
Reinhard Stierl
Frank Werner
Maria Scherer
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BASF SE
Original Assignee
BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP06763960A priority Critical patent/EP1903867A1/fr
Publication of EP1903867A1 publication Critical patent/EP1903867A1/fr
Withdrawn legal-status Critical Current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 comprising as active components 1) at least one 3,5-disubstituted pyrazolecarboxylic acid biphenylamide of the formula I.
  • R 1 and R 2 independently of one another are cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -
  • Haloalkyl methoxy, difluoromethoxy or trifluoromethoxy
  • R 3 is halogen, -C 4 -alkyl or Ci-C 4 haloalkyl
  • R 4 is hydrogen or halogen
  • Azoles selected from bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon , Triadimol, tebuconazole, tetraconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamide, benomyl, carbendazim, thiadanazole, fuberidazole, ethaboxam, etridiazole and hymexazole
  • Carboxylic acid amides selected from carboxin, benalaxyl, boscalid, fenhexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro-N- (2) cyanopheny O-isothiazole- ⁇ -carboxamide, dimethomorph, flumorph, fl uidover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet, mandipropamide, N- (2- [4- [3- (4-chloro-phenyl) -propyl] 2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methanesulfonylamino-3-methylbutyrannide
  • R 5 is methyl or ethyl
  • Heterocyclic compounds selected from fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforin, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, family oxadone, 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, pyroquilone, proquinazide, tricyclazole, the compound of formula IV (2-butoxy-6-iodo-3
  • 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, toiolo-fos-methyl,
  • Organochlorine Compounds Chlorothalonil, Dichlofluanid, Flusulfamide, Hexachlorobenzene, Phthalide, Pencycuron, Quintozen, Thiophanate-Methyl, Toiylfluanide,
  • Inorganic active ingredients Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur,
  • Cyflufenamid Cymoxanil, Dimethirimol, Ethirimol, Furalaxyl, Metrafenone and Spiroxamine;
  • 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, however, are only monosubstituted on the biphenyl radical.
  • 2,4-Disubstituted biphenylamides are known from WO 2005/123689 and WO 2005/123690, and 3,5-disubstituted biphenylamides are known from the earlier German Application No. 102005007160.0.
  • 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.
  • 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-ylidenmalonate (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, n-methyl ester (WO 96/01256); Trifloxystrobin, methyl (E) -methoxyimino ⁇ (E) - ⁇ - [1- ( ⁇ , ⁇ , ⁇ -trifluoro-m-tolyl) ethylideneaminooxy] -o-tolyl ⁇ acetate (EP-A 460 575);
  • the present invention was based on mixtures which have an improved action against harmful fungi, in particular for certain indications, with a reduced total amount of active substances applied.
  • 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-methyl-propyl, preferably a Ci-C 4 -
  • Ci-C 4 haloalkyl is a partially or completely halogenated Ci-C 4 alkyl rest, wherein the / the halogen atom (s), especially fluorine, chlorine and / or bromine is / 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-chloroethyl 2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethy
  • C 1 -C 6 -haloalkyl represents a partially or completely halogenated C 1 -C 6 -alkyl radical, where the halogen atom (s) is, in particular, fluorine, chlorine and / or bromine, ie, for example, a C 1 -C 4 -haloalkyl radical as mentioned above, or for 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, 5,5,5-trichloropentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6- lodhexyl, 6,6,6-trichlorohexyl or Dodecafluorhexyl, preferably a Ci-C 4 haloalkyl group.
  • 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).
  • X is oxygen
  • those in which X is oxygen are preferred.
  • R 1 and R 2 are independently cyano, fluorine, chlorine, methyl, methoxy or trifluoromethyl
  • R 3 is fluorine, chlorine, methyl or Ci-haloalkyl
  • R 4 is hydrogen or halogen.
  • R 1 and R 2 independently of one another are cyano, fluorine, chlorine or methoxy and R 3 is fluorine, chlorine, methyl, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl and R 3 4 represent hydrogen, fluorine or chlorine.
  • R 1 and R 2 independently of one another, are fluorine or chlorine
  • R 3 is methyl, fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl
  • R 4 is hydrogen
  • Very particularly preferred compounds of the formula I are 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (3 ', 5'-dichlorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl 1-H-pyrazole-4-carboxylic acid N- (3 ', 5'-difluorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (3'-chloro-5'-fluorobiphenyl-2-yl) -amide, 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (3 ', 5'-bis (trifluoromethyl) biphenyl-2 -yl) -amide, 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid N- (3 ', 5'-dichlorobiphenyl-2-yl) -amide, 1-
  • 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
  • A) azoles selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadimenol, tebucon
  • active substance selected from the group of A) azoles selected from epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim.
  • B) strobilurins selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclobutin and trifloxystrobin 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.
  • 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-trifluorophenyl)
  • active compound selected from the group consisting of E) carbamates selected from mancozeb, metiram, propineb, thiram, iprovalicarb, flubenthiavalicarb and propamocarb 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.
  • 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, Deuteromycetes, Basidiomycetes, Peronospo- romyceten (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,
  • Drechslera species Pyrenophora species on corn, cereals, rice and turf, e.g. D. teres to barley or D. tritici-repentis to wheat,
  • 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, - Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans,
  • Phytophthora species on various plants e.g. P. capsici on paprika
  • 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,
  • Rhizoctonia species on cotton, rice, potatoes, turf, corn, rapeseed, sugar beets, vegetables and on various plants e.g. R. solani on beets and various plants, - Rhynchosporium secalis on barley, rye and triticale,
  • 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.
  • mixtures according to the invention are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions,
  • 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 mixtures are applied by treating the fungi or the plants, seeds, materials or soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
  • the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
  • 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 substances I to II are preferably used in the preparation of the mixtures, 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 substances consist of a mixture of a compound of formula I, particularly 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid-N- (3 ', 5 1 - difluorobiphenyl-2-yl) -amide, 1-Methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid N- (3 ', 5 1 -dichlorobiphenyl-2-yl) -amide, 1-methyl-3-difluoromethyl-1H-pyrazole-4 carboxylic acid-N- (3 ', 5 1 - difluorobiphenyl-2-yl) amide or 1-methyl-3-difluoromethyl-1 H-pyrazole-4-carboxylic acid-N- (S'. ⁇ '-dichlorobiphenyl ⁇ -y ⁇ amide, an azole from group A), in particular epoxiconazole, metconazole, triticonazole or fluquinconazole, and
  • 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.
  • Compound (s) I and active compound (II) II are usually used in a weight ratio of from 100: 1 to 1: 100, preferably from 20: 1 to 1:20, in particular from 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 ingredients II are correspondingly generally 1 to 2000 g / ha, preferably 1 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 can be converted into the customary formulations.
  • be transferred 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 / auxiliary materials 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.
  • Carriers 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 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 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.
  • 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, for example, 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, cellulose powder or 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 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 of 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.
  • Uniperol ® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the active ingredients epoxiconazole and pyraclostrobin were used as a commercially available ready-made formulation and diluted with water to the stated active substance concentrations. The visually determined values for the percentage of affected leaf areas were converted into efficiencies as% of the untreated control.
  • the efficiency (W) was determined 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.
  • Leaves of potted tomato plants were sprayed to drip point with an aqueous suspension in the drug concentration below. The following day, the leaves were infected with an aqueous spore suspension of Alternaria solani in 2% biomalt solution with a density of 0.17 ⁇ 10 6 spores / ml. The plants were then placed in a water vapor-saturated chamber at temperatures between 20 and 22 0 C. After 5 days, the disease on the untreated, but infected control plants had developed so strongly that the infestation could be determined visually in%.
  • 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 humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.
  • Leaves of potted wheat seedlings were sprayed to drip point with aqueous suspension in the concentration of active compound given below.
  • the suspension or emulsion was prepared as described above. 24 hours after the spray coating has dried on spores of wheat powdery mildew (Erysiphe [syn. graminis fomna specialis. tritici) pollinated.
  • the test plants were then placed in a greenhouse at temperatures between 20 and 24 ° C and 60 to 90% relative humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area.

Abstract

La présente invention concerne des mélanges fongicides contenant comme composantes actives: 1) au moins un biphénylamide d'acide pyrazolcarboxylique 3,5-disubstitué de formule (I) dans laquelle X = oxygène ou soufre; R<SUP>1</SUP> et R<SUP>2</SUP> = cyano, nitro, halogène, alkyle en C<SUB>1</SUB>-C<SUB>6</SUB>, halogénalkyle en C<SUB>1</SUB>-C<SUB>6</SUB>, méthoxy, difluorméthoxy ou trifluorméthoxy; R<SUP>3</SUP> = halogène, alkyle en C<SUB>1</SUB>-C<SUB>4</SUB> ou halogénalkyle en C<SUB>1</SUB>-C<SUB>4</SUB>; R<SUP>4</SUP> = hydrogène ou halogène; et 2) au moins un principe actif II choisi dans les groupes A) à F): A) les azoles; B) la strobilurine; C) les amides d'acide carboxylique; D) les composés hétérocycliques; E) les carbamates; F) d'autres fongicides, en une quantité synergiquement active. L'invention a également pour objet un procédé pour lutter contre des champignons parasites au moyen de mélanges composés d'au moins un composé I et d'au moins un principe actif II, l'utilisation du/des composé(s) I avec des principes actifs II pour préparer de tels mélanges, ainsi que des substances et des semences contenant ces mélanges.
EP06763960A 2005-07-01 2006-06-29 Melanges fongicides a base de biphenylamides d'acide pyrazolcarboxylique 3,5-disubstitues Withdrawn EP1903867A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP06763960A EP1903867A1 (fr) 2005-07-01 2006-06-29 Melanges fongicides a base de biphenylamides d'acide pyrazolcarboxylique 3,5-disubstitues

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102005031199 2005-07-01
EP06101427 2006-02-08
EP06763960A EP1903867A1 (fr) 2005-07-01 2006-06-29 Melanges fongicides a base de biphenylamides d'acide pyrazolcarboxylique 3,5-disubstitues
PCT/EP2006/063664 WO2007003564A1 (fr) 2005-07-01 2006-06-29 Melanges fongicides a base de biphenylamides d'acide pyrazolcarboxylique 3,5-disubstitues

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EP1903867A1 true EP1903867A1 (fr) 2008-04-02

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EP (1) EP1903867A1 (fr)
JP (1) JP2009500311A (fr)
AR (1) AR056408A1 (fr)
BR (1) BRPI0612804A2 (fr)
GT (1) GT200600293A (fr)
PE (1) PE20070422A1 (fr)
TW (1) TW200740371A (fr)
UY (1) UY29646A1 (fr)
WO (1) WO2007003564A1 (fr)

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PT1912503E (pt) 2005-08-05 2014-10-02 Basf Se Misturas fungicidas contendo anilidas do ácido 1-metilpirazol-4-ilcarboxílico substituídas
WO2007110173A2 (fr) * 2006-03-24 2007-10-04 Bayer Cropscience Ag Combinaisons de substances actives fongicides
EA017319B1 (ru) * 2007-02-05 2012-11-30 Басф Се Фунгицидные смеси, содержащие замещённые 1-метилпиразол-4-илкарбоксанилиды
WO2008135480A2 (fr) * 2007-05-02 2008-11-13 Basf Se Lutte contre un pathogène fongique spécifique au soja avec du bénodanile
CN103907610B (zh) * 2013-01-06 2016-05-04 江苏丰登作物保护股份有限公司 一种含氟唑菌酰胺和啶氧菌酯的杀菌组合物及其应用

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TW384208B (en) * 1995-09-22 2000-03-11 Basf Ag Compositions and methods for controlling harmful fungi
TW491686B (en) * 1997-12-18 2002-06-21 Basf Ag Fungicidal mixtures based on amide compounds and tetrachloroisophthalonitrile
TW431861B (en) * 1997-12-18 2001-05-01 Basf Ag Fungicidal mixtures based on amide compounds and azoles
PL191024B1 (pl) * 1997-12-18 2006-03-31 Basf Ag Mieszanina grzybobójcza
DE10347090A1 (de) * 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
US20070197556A1 (en) * 2004-05-13 2007-08-23 Tormo I Blasco Jordi Fungicidal Mixtures
ATE458722T1 (de) * 2004-06-18 2010-03-15 Basf Se 1-methyl-3-trifluormethyl-pyrazol-4-carbonsäure (ortho-phenyl)-anilide und ihre verwendung als fungizid
CN1968934A (zh) * 2004-06-18 2007-05-23 巴斯福股份公司 N－(邻苯基)－1－甲基－3－二氟甲基吡唑－4－甲酰苯胺及其作为杀真菌剂的用途
DE102004045242A1 (de) * 2004-09-17 2006-03-23 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen

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TW200740371A (en) 2007-11-01
JP2009500311A (ja) 2009-01-08
UY29646A1 (es) 2007-01-31
BRPI0612804A2 (pt) 2016-11-29
PE20070422A1 (es) 2007-04-25
WO2007003564A1 (fr) 2007-01-11
GT200600293A (es) 2007-09-27
AR056408A1 (es) 2007-10-10

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