WO2009071450A1 - Mélanges fongicides - Google Patents

Mélanges fongicides Download PDF

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Publication number
WO2009071450A1
WO2009071450A1 PCT/EP2008/065964 EP2008065964W WO2009071450A1 WO 2009071450 A1 WO2009071450 A1 WO 2009071450A1 EP 2008065964 W EP2008065964 W EP 2008065964W WO 2009071450 A1 WO2009071450 A1 WO 2009071450A1
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Prior art keywords
methyl
pyrazole
phenyl
difluoromethyl
carboxamide
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PCT/EP2008/065964
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German (de)
English (en)
Inventor
Jens Renner
Sarah Ulmschneider
Jochen Dietz
Egon Haden
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Basf Se
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Publication of WO2009071450A1 publication Critical patent/WO2009071450A1/fr

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    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • A is phenyl which is substituted by three F
  • B is unsubstituted pyridyl, thienyl, thiazolyl, oxazolyl or furyl or phenyl which is substituted by one to three of the following substituents: halogen, NO 2 , amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 haloalkyl, Ci-C 4 - haloalkoxy, Ci-C 4 alkylamino, Ci-C 4 dialkylamino, thio, or Ci-C 4 -
  • Azoxystrobin Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methyminostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, 3-methoxy- 2- (2- (2- (N- (4-methoxy-phenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester, 2- (2- (3- (2,6-dichlorophenyl) -1-methyl-ally
  • carboxylic acid anilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carbo-xin, fenfuram, fenhexamide, flutolanil, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin,
  • carboxamides carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;
  • Triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, mycelobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazo -
  • - imidazoles cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizo- Ie;
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 3- [5- (4-methyl-phenyl) -2, 3-dimethyl-isoxazolidin-3-yl] -pyridine, 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloropyridine-2,6-dicarbonitrile, N- (1 - (5-bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloro-nicotinamide, N - ((5-bromo-3-chloro-pyridin-2-yl) -methyl) -2 , 4-dichloro-nicotinamide;
  • - pyrimidines bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrimine, nitrapyrin, nuarimol, pyrimethanil;
  • Dicarboximides fluoroimide, iprodione, procymidone, vinclozolin;
  • non-aromatic 5-membered heterocycles famoxadone, fenamidone, flutianil, octhi- non, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydropyrazole-1-thiocarboxylic acid allyl ester;
  • Thio and dithiocarbamates Ferbam, Mancozeb, Maneb, Metam, Methasulphocarb, Metiram, Propineb, Thiram, Zineb, Ziram; - Carbamates: Diethofencarb, Benthiavalicarb, Iprovalicarb, Propamocarb, Propamocarb hydrochloride, Valiphenal, N- (1- (1- (4-cyanophenyl) ethanesulfonyl) -but-2-yl) carbamic acid (4-fluorophenyl) ester ;
  • fungicides selected from - guanidines: dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilat);
  • antibiotics kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A;
  • Nitrophenyl derivatives binapacryl, diclorane, dinobutone, dinocap, nitrothal-isopropyl, tecnazene;
  • Fentin salts such as, for example, fentin acetate, fentin chloride, fentin hydroxide;
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl;
  • Organochlorine compounds chlorothalonil, dichlofluanid, dichlorophen, flusulfamides, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phtha-Nd, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitrophenyl) -N- ethyl-4-methyl-benzenesulfonamide; - Inorganic active substances: Phosphorous acid and its salts, sulfur, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate;
  • the invention relates to the use of fungicidal mixtures for combating phytopathogenic fungi and agents or compositions containing them.
  • Azolylmethyloxiranes of component 1 their preparation and their use in crop protection are known from WO2007147769 and the underlying EP 061 15929.9.
  • component 2 The active ingredients mentioned above as component 2, their preparation and their action against harmful fungi are known (see: http: //www.hclrss. Demon.co.uk/index.html; http://www.alanwood.net/pesticides /); they are commercially available.
  • the compounds named after IUPAC, their preparation and their fungicidal action are also known (see Can. J.
  • the present invention was based on mixtures which were applied at a reduced total amount Active ingredients have an improved action against harmful fungi, especially for certain indications show.
  • the present invention therefore also relates in particular to fungicidal compositions which comprise at least one compound of the general formula I and at least one further fungicidal active ingredient (component 2), eg. One or more, e.g. 1 or 2 active substances of the abovementioned groups 2.1 to 2.6 and optionally one or more agriculturally suitable carriers. It has also been found that with simultaneous joint or separate application of the compound I and the compound II or when using the compound I and the compound II successively control fungi better than with the individual compounds (synergistic mixtures).
  • the at least one compound I and the at least one further active ingredient at the same time ie the attacking plant-damaging fungi and their habitat such as infested plants, plant propagation materials, insebesondere seed, soil, materials or spaces and the plants to be protected against fungal attack, plant propagation materials, in particular seeds, soil, materials or rooms
  • the attacking plant-damaging fungi and their habitat such as infested plants, plant propagation materials, insebesondere seed, soil, materials or spaces and the plants to be protected against fungal attack, plant propagation materials, in particular seeds, soil, materials or rooms
  • the time sequence of the application of the active ingredients is of minor importance.
  • the compound I is able to form salts or adducts with inorganic or organic acids or with metal ions because of the basic character of the nitrogen atoms contained in them.
  • inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
  • suitable organic acids are formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), Arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl bearing one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), aryl
  • the metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, the third and fourth main groups, in particular aluminum, tin and lead, and the first to eighth transition groups, in particular chromium, manganese, iron, cobalt, nickel, Copper, zinc and others into consideration. Particularly preferred are the metal ions of the elements of the subgroups of the fourth period.
  • the metals can be present in the various valences that belong to them.
  • Halogen fluorine, chlorine, bromine and iodine
  • Haloalkyl Alkyl as mentioned above, wherein in these groups partially or completely the hydrogen atoms are replaced by halogen atoms as mentioned above.
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluoro, chloro or bromo.
  • the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred. Particular preference is given to (C 1 -C 4) -haloalkyl, more preferably (C 1 -C 2) -haloalkyl, such as chloromethyl,
  • Alkoxy for an oxygen-bonded alkyl group as defined above, preferably having 1 to 4 carbon atoms.
  • alkoxy groups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy.
  • Haloalkoxy alkoxy, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine.
  • haloalkoxy radicals are OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2 , 2-Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5 , 2-fluoro
  • Alkylthio Alkyl as defined above attached via an S atom.
  • the compounds of formula I contain chiral centers and are generally obtained in the form of racemates or as mixtures of diastereomers of erythro and threo forms.
  • the erythro and threo diastereomers can be separated in the compounds of the invention, for example, due to their different solubility or by column chromatography and isolated in pure form.
  • Uniform uniform enantiomers can be obtained from such uniform pairs of diastereomers by known methods.
  • fungicidal agents it is possible to use both the uniform diastereomers or enantiomers and also their mixtures obtained in the synthesis.
  • Enantiomeric pairs or enantiomers with cis-arrangement of ring B and triazolylmethyl substituent are preferred here.
  • the compounds I may be present in various crystal modifications whose biological activity may be different. These are included in the scope of the present invention.
  • the substituent A is phenyl which is substituted by three F, so that a total of six substituents A1 to A6 of the following formulas result:
  • A is A1, A2, A3 or A4.
  • A is A1 or A2.
  • A is A1.
  • A is A2.
  • A is A3.
  • A stands for A4.
  • A is A5 or A6.
  • A is A5.
  • A is A6.
  • Another embodiment relates to compounds I in which B is unsubstituted pyridyl, thienyl, thiazolyl, oxazolyl or furyl.
  • B is pyridyl or thienyl.
  • B is pyridyl
  • B is phenyl substituted by one to three of the following substituents: halogen, NO2, amino, Ci-C 4 -alkyl, C 4 -alkoxy, Ci-C d-4 haloalkyl, Ci-C4- Haloalkoxy, Ci-C 4 alkylamino, CrC 4 - dialkylamino, thio or Ci-C 4 alkylthio is substituted.
  • B is phenyl, 4 alkyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy substituted by one to three of the following substituents: halogen, Ci-C 4 haloalkyl or C C.
  • B is phenyl substituted by one to three halogens.
  • the invention relates to fungicidal mixtures containing as active components 1) Azolylmethyloxirane of the general formula I, wherein
  • A is phenyl which is substituted by three F
  • B is unsubstituted pyridyl, thienyl, thiazolyl, oxazolyl or furyl or phenyl which is substituted by one to three of the following substituents: halogen, NO 2 , amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 haloalkyl, Ci-C 4 - haloalkoxy, Ci-C 4 alkylamino, Ci-C 4 dialkylamino, thio, or Ci-C 4 - alkylthio,
  • Azoxystrobin Dimoxystrobin, Enestroburin, Fluoxastrobin, Kresoxim-methyl, Methyminostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyribencarb, Trifloxystrobin, 2- (2- (6- (3-Chloro-2-methyl-phenoxy) -5-fluoro) pyrimidin-4-yloxy) -phenyl) -2-methoxyimino-N-methyl-acetamide, 2- (ortho - ((2,5-dimethylphenyl-oxymethylene) -phenyl) -3-methoxy-acrylic acid methyl ester, 3-methoxy- 2- (2- (N- (4-methoxyphenyl) -cyclopropanecarboximidoylsulfanylmethyl) -phenyl) -acrylic acid methyl ester;
  • Carboxylic acid amides selected from - carboxylic acid anilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboin, fenfuram, fenhexamide, flutolanil, furametpyr, isotianil, kiralaxyl, mepronil, metalaxyl, ofurace, oxadixyl, oxycarboxine, penthiopyrad, tecloftalam , Thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxylic acid anilide, 2-chloro-N- (1, 1, 3-trimethyl-indan-4-yl) -nicotinamide, N- ( 3 ', 4'-dichloro-5-fluoro-biphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole-4
  • Benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide;
  • carboxamides carpropamide, diclocymet, mandipropamide, oxytetracycline, silthiofam, N- (6-methoxypyridin-3-yl) cyclopropanecarboxamide;
  • Azoles selected from - triazoles azaconazole, bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, mycelobutanil, oxpoconazole, paclobutrazole , Penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1- (4-chloro-phenyl) -2 - ([1, 2,4] -triazol-1-yl ) cycloheptano
  • Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole;
  • Pyridines fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethyl-isoxazolidin-3-yl] -pyridine, 2,3,5,6-tetrachloro-4-methanesulphonyl-pyridine 3,4,5-trichloropyridine-2,6-dicarbonitrile, N- (1- (5-bromo-3-chloro-pyridin-2-yl) -ethyl) -2,4-dichloro-nicotinamide , N - ((5-
  • - pyrimidines bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrimine, nitrapyrin, nuarimol, pyrimethanil;
  • Dicarboximides fluoroimide, iprodione, procymidone, vinclozolin; - others: acibenzolar-S-methyl, amisulbrom, anilazine, blasticidin-S, captafol, captan, quinomethionate, dazomet, debacarb, diclomethine, difenzoquat, difenzoquatemethylsulphate, famoxadone, fenamidone, fenoxanil, fenpropidin, folpet, octhilinone , Oxolinic acid, piperine, samplesazoles, proquinazide, pyroquilon, quinoxyfen, triazoxide, tricyclazoles, triforines, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1, 2,4] triazolo [1,5-a]
  • Guanidines dodine, dodine free base, guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilat);
  • Fentin salts such as, for example, fentin acetate, fentin chloride, fentin hydroxide;
  • Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone;
  • Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl;
  • Organochlorine compounds chlorothalonil, dichlofluanid, dichlorophen, flusulfamides, hexachlorobenzene, pencycuron, pentachlorophenol and its salts, phtha-Nd, quintozene, thiophanate-methyl, tolylfluanid, N- (4-chloro-2-nitrophenyl) -N- ethyl-4-methyl-benzenesulfonamide;
  • Inorganic active substances Phosphorous acid and its salts, sulfur, Bordeaux broth, copper salts such as copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate;
  • Preferred compounds II are selected from azoxystrobin, kresoxim-methyl, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • Further preferred compounds II are selected from azoxystrobin, kresoximethyl, pyraclostrobin and trifloxystrobin.
  • Preferred compounds II are also carboxin, bixafen, penthiopyrad, pyrimidinedione, metalaxyl, N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazole 4-carboxamide, N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (cis-bicyclopropyl-2-yl-phenyl) -3 -difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (trans-2-bicyclopropyl-2-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- ( 2'-fluoro-4'-chloro-5'-methyl-biphenyl
  • Preferred compounds II are selected bixafen, N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N- (cis-bicyclopropyl-2-yl-phenyl ) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (trans-2-bicyclopropyl-2-phenyl) -3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide, N- (2'-fluoro-4'-chloro-5'-methyl-biphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3
  • Preferred compounds II are selected from cyproconazole, difenoconazole, epoxiconazole, flusilazole, flutriafol, myclobutanil, metconazole, propiconazole, prothioconazole, tebuconazole, tetraconazole, prochloraz.
  • Preferred compounds II are selected from cyproconazole, epoxiconazole, metconazole, propiconazole, prothioconazole, tebuconazole, tetraconazole, prochloraz.
  • Preferred compounds II are selected from carbendazim, thiabendazole, cyprindinil, fludioxonil, fenpropimorph, captan, fenpropidin, thiram, chlorothalonil, thiphanate-methyl, sulfur, copper hydroxide, metrafenone and spiroxamine.
  • Preferred compounds II are selected from carbendazim, fenpropimorph and metrafenone.
  • the compound II is selected from azoxystrobin, flutriafol, spiroxamine, metrafenone, epoxiconazole, metconazole, trifloxystrobin, thiram and N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methyl- 1 H-pyrazole-4-carboxylic acid amide.
  • compositions of a compound I with at least one active compound from group 2.1) (component 2) of the strobilurins and especially selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
  • compositions of a compound I having at least one active compound selected from the group 2.2 (component 2) of the carboxamides and especially selected from hexhexamide, metalaxyl, mefenoxam, ofuracene, dimethomorph, flumorph, fluopicolide (picobenzamide) , Zoxamide, carpropamide and mandipropamide.
  • compositions of a compound I having at least one active compound selected from the group 2.3.
  • Component 2 of the azo and especially selected from cyproconazole, difenoconazole, epoxiconazole, fluconconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamide, Benomyl, carbendazim and ethaboxam.
  • compositions of a compound I having at least one active compound selected from group 2.4 (component 2) of the nitrogen-containing heterocyclyl compounds and especially selected from fluazinam, Cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, fodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole, proquinazide, acibenzolar-S-methyl, captafol, folpet, fenoxanil and quinoxyfen.
  • component 1 having at least one active compound selected from group 2.4 (component 2) of the nitrogen-containing heterocyclyl compounds and especially selected from fluazinam, Cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforin, fludioxonil, fodemorph, fenpropimorph
  • compositions of a compound I having at least one active compound selected from the group 2.5 (component 2) of the carambamates and especially selected from mancozeb, metiram, propineb, thiram, iprovalacarb, flubenthiavalicarb and propamocarb.
  • compositions of a compound I with at least one active ingredient selected from the fungicides of group 2.6 (component 2) and especially selected from dithianone, fentin salts such as fentin acetate, fosetyl, fosetyl-aluminum, H3PO3 and their salts, Chlorothalonil, dichlofluanid, thiophosphate-methyl, copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, cymoxanil, metrafenone, spiroxamine and 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6 -trifluorophenyl) - [1, 2,4] -triazolo [1,5-a] pyrimidine.
  • fentin salts such as fentin acetate, fosetyl, fosetyl-aluminum, H3PO3 and their salts
  • Chlorothalonil dichlo
  • the present invention further relates to the compositions listed in Table A, wherein in each case one row of Table A corresponds to a fungicidal composition comprising a compound of formula I (component 1), which is preferably one of the compounds described herein as preferred, and in each case indicated in the relevant line further active ingredient II (component 2).
  • component 1 in each row of table 2 is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 7.
  • Rapeseed mustard, olives, sunflowers, coconut, cocoa, castor beans, oil palm, peanuts or soya
  • Cucurbits z. Pumpkins, cucumbers or melons
  • Fiber plants z. Cotton, flax, hemp or jute
  • Citrus fruits z. Oranges, lemons, grapefruits or mandarins
  • Vegetables z. Spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, squash or paprika
  • Energy and raw material plants eg.
  • Corn soy, wheat, rapeseed, sugarcane or oil palm; Corn; Tobacco; Nuts; Coffee; Tea; bananas; Wine (table and grapes); Hop; Grass, z. B. lawn; Rubber plants; Ornamental and forest plants, z. As flowers, shrubs, deciduous and coniferous trees and on the propagation material, for. B. seeds, and the crop of these plants.
  • Fruit, vine and ornamental plants and vegetables eg. As cucumbers, tomatoes, beans and pumpkins and on the propagation material, for. As seeds, and the crop of these plants used.
  • plant propagating materials includes all generative parts of the plant, e.g. As seeds, and vegetative plant parts, such as cuttings and tubers (eg., Potatoes), which can be used to propagate a plant. These include seeds, roots, fruits, tubers, bulbs, rhizomes, shoots and other plant parts, including seedlings and seedlings, which are transplanted after germination or emergence.
  • the young plants can be treated by a partial or complete treatment, eg. B. by immersion or pouring, are protected from harmful fungi.
  • Compounds I and II are used for controlling a multiplicity of fungal pathogens in cereal crops, eg. Wheat, rye, barley or oats; Rice, corn, cotton and soy used.
  • cereal crops eg. Wheat, rye, barley or oats; Rice, corn, cotton and soy used.
  • crops also includes those plants which, by breeding,
  • Mutagenesis or genetic engineering methods have been modified, including marketed or under development biotechnological agricultural products (see, for example, http://www.bio.org/speeches/pubs/ er / agri_products.asp).
  • Genetically engineered plants are plants whose genetic material has been altered in a manner that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information).
  • one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.
  • Such genetic engineering also includes post translational modifications of proteins, oligo or polypeptides, e.g. by glycolylation or binding of polymers such as e.g. prenylated, acetylated or farnelysierter residues or PEG residues.
  • plants may be mentioned which, by means of breeding and genetic engineering measures, tolerate certain types of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) -I inhibitors, such as, for example, Sulfonylureas (EP-A 257 993, US Pat. No. 5,013,659) or imidazolinones (for example US Pat. No.
  • herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) -I inhibitors, such as, for example, Sulfonylureas (EP-A 257 993, US Pat. No. 5,013,659) or imidazolinones (for example US Pat. No.
  • EPSPS enolpyruvylshikimate-3-phosphate synthase
  • Glyphosate see, for example, WO 92/00377)
  • glutamine synthetase (GS) inhibitors such as.
  • Glufosinate see eg EP-A 242 236, EP-A 242 246) or oxynil herbicides (see eg US 5,559,024).
  • crop plants such as soybean, produces cotton, corn, beets and rape, which are resistant to glyphosate or glufosinate, and sold under the trade name rou- dupReady ® (glyphosate-resistant, Monsanto, USA) and Liberty Link ® (Glufosinat- resistant, Bayer CropScience, Germany) are available.
  • plants are included which, with the aid of genetic engineering measures one or more toxins, eg. B. those from the bacterial strain Bacillus produce.
  • Toxins produced by such genetically engineered plants include e.g. B. insecticidal proteins of Bacillus spp., In particular of B.
  • thuringiensis such as the endotoxins Cry1 Ab, Cry1 Ac, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g. VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g.
  • 3-hydroxy steroid oxidase ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase
  • ion channel blocker e.g. B. inhibitors of sodium or calcium channels
  • Juvenile hormone esterase e.g. B. inhibitors of sodium or calcium channels
  • Receptors for the diuretic hormone (helicokinin receptors) e.g. B. inhibitors of sodium or calcium channels
  • Receptors for the diuretic hormone (helicokinin receptors) helicokinin receptors
  • Stilbene synthase bibenzyl synthase, chitinases and glucanases.
  • These toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are described in EP-A 374 753, WO 93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073 discloses. The methods for producing these genetically modified plants are known to the person skilled in the art and z. As set forth in the publications mentioned above.
  • YieldGard ® (corn cultivars producing the toxin CrylAb), YieldGard ® Plus (corn cultivars producing the toxins CrylAb and Cry3Bb1), StarLink ® (corn cultivars producing the toxin Cry9c), Herculex ® RW (corn cultivars produce the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase [PAT]); NuCOTN ® 33B (cotton cultivars producing the toxin CrylAc), Bollgard ® I (cotton cultivars producing the toxin CrylAc), Bollgard ® Il (cotton cultivars producing the toxins CrylAc and Cry2Ab2); VIP COT ® (cotton cultivars producing a VIP-toxin); NewLeaf ® (potato cultivars producing the Cry3A toxin); Bt Xtra ®, NatureGard® ®, KnockOut ®
  • plants which produce by genetic engineering measures one or more proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens, such as.
  • proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens
  • pathogenesis-related proteins PR proteins, see EP-A 0 392 225
  • resistance proteins eg potato varieties which produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum
  • T4 lysozyme For example, potato varieties that are resistant to bacteria such as Erwinia amylvora through the production of this protein.
  • plants are included whose productivity with the help of genetic engineering
  • Methods has been improved by z.
  • yield eg biomass, grain yield, starch, oil or protein content
  • plants are included whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z.
  • As oil plants producing health long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids eg Nexera ® - rape, DOW Agro Sciences, Canada.
  • plants are included, which have been modified for the improved production of raw materials by means of genetic engineering methods by z.
  • the amylopectin content of potatoes (Amflora® potato, BASF SE, Germany) was increased.
  • Albugo spp. White rust on ornamental plants, vegetable crops (eg A. Candida) and sunflowers (eg BA tragopogonis); Alternaria spp. (Blackness, black spotiness) on vegetables, oilseed rape (for example BA brassicola or A. brassicae), sugar beet (for example BA tenuis), fruit, rice, soybeans and on potatoes (eg A. solani or A. alternata) and tomatoes (eg BA solani or A. alternata) and Alternaria spp. (Earwires) on wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, eg.
  • Botrytis cinerea Botryotina fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including lettuce, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (ear fungus); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz) on deciduous and coniferous trees, z.
  • Botrytis cinerea Triomorph: Botryotina fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including lettuce, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (ear fungus); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz)
  • BC ulmi elm dying, Dutch elm disease
  • Cercospora spp. Cercospora leaf spot
  • maize eg BC zeae-maydis
  • sugar beets eg BC beticola
  • sugarcane vegetables
  • coffee soybeans
  • soybeans eg BC sojina or C. kikuchii
  • Cladosporium spp. on tomato eg BC fulvum: velvet spot disease
  • cereals eg.
  • BC herbarum (earwax) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (Anamorph: Helminthosporium or Bipolaris) spp. (Leaf spot) on maize (for example BC carbonum), cereals (for example B. sativus, anamorph: B. sorokinia-na: brown spot) and rice (for example BC miyabeanus, anamorph: H. oryzae); Colletotricum (teleomorph: Glomerella) spp.
  • Focal spots Entyloma oryzae (leaf sting) on rice; Epicoccum spp. (Earwires) on wheat; Erysiphe spp. (Powdery mildew) on sugar beet (E. betae), vegetables (eg BE pisi), such as cucumber (for example BE cichoracearum) and cabbage plants, such as rapeseed (for example, B. cruciferarum); Eutypa lata (Eutypa crab or extinction, anamorphic Cytosporina lata, Syn. Libertella blepharis) on fruit trees, vines and many ornamental shrubs; Exserohilum (Syn. Helminthosporium) spp.
  • BH vastatrix (coffee leaf rust) of coffee; Isariopsis clavispora (Syn. Cladosporium vitis) on grapevine; Macrophomina phasolina (Syn. Phaseoli) (root / stem rot) on soybeans and cotton; Micro- nium (Syn. Fusarium) nivale (snow mold) on cereals (eg wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., Z. BM laxa, M. fructicola and M. fructigena (flower and lace drought) on stone fruits and other rosaceae; Mycosphaerella spp.
  • BM graminicola Anamorph: Septoria tritici, Septoria leaf drought
  • M. fijiensis Black Sigatoka disease
  • Peronospora spp. Downy mildew
  • cabbage for example BP brassicae
  • oilseed rape for example P. parasitica
  • onion for example BP destructor
  • tobacco for example BP destructor
  • soybeans for example P. manshuricum
  • Grapevines eg BP tracheiphila and P. tetraspora
  • soybeans eg BP gregata: stalk disease
  • Phoma Hungary root and stem rot
  • oilseed rape and cabbage and P. betae leaf spots
  • Phomopsis spp. on sunflowers
  • grapevine eg BP viticola: black spot disease
  • soybeans eg stalk rot: P. phaseoli, teleomorph: Diaporthe phaseolorum
  • Physoderma maydis (brown spot) on maize
  • BP capsici e.g. BP capsici
  • soybeans eg BP megasperma, Syn. P. sojae
  • potatoes and tomatoes eg. BP infestans: herbaceous and brown rot
  • deciduous trees eg BP ramorum: sudden oak mortality
  • Plasmodiophora brassicae cabbage hernia
  • Plasmopara spp. E.g. BP viticola (vine peronospora, downy mildew) on vines and P.
  • Podosphaera spp. Panosphaera spp. (Powdery mildew) of rosaceae, hops, kernels and berries, eg. BP leucotricha to apple; Polymyxa spp., Z. To cereals such as barley and wheat (P. graminis) and sugar beet (P. betae) and the viral diseases conferred thereby; Pseudocercosporella herpotrichoides (straw break, teleomorph: Tapesia yallundae) on cereals, e.g. Wheat or barley; Pseudoperonospora (downy mildew) on various plants, e.g.
  • BP cubensis on cucurbits or P. humili on hops Pseudo-pezicula tracheiphila (red burner, anamorph: Phialophora) on grapevine; Puccinia spp. (Rust disease) on various plants, eg. BP triticina (wheat brown rust), P. striiformis (yellow rust), P. hordei (dwarf rust), P. graminis (black rust) or P. recondita (rye brown rust) on cereals, such as.
  • BP asparagi Pyrenophora (anamorph: Drechslera) tritici-repentis (leaf drought) on wheat or P. teres (netted spots) on barley; Pyricularia spp., E.g. BP oryzae (Teleomorph: Magnaporthe grisea, rice leaf-fire) on rice and P. grisea on lawn and crops; Pythium spp. (Turnip disease) on turf, rice, corn, wheat, Cotton, rapeseed, sunflower, sugar beet, vegetables and other plants (eg BP ultimum or P. aphanidermatum); Ramularia spp., Z.
  • Pyrenophora anamorph: Drechslera) tritici-repentis (leaf drought) on wheat or P. teres (netted spots) on barley
  • Pyricularia spp. E.g. BP oryzae (Teleomorph: Magnaport
  • BR collo-cygni (speckled disease / sunburn complex / Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, oilseed rape, potatoes, sugar beets, vegetables and various other plants, eg. BR solani (root / stem rot) on soybeans, R. solani (leaf-sheathing) on rice or R.
  • cerealis pointed eye-spot on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevine and tomato; Rhynchosporium secalis (leaf spot) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (Stem or white rot) in vegetables and crops such as oilseed rape, sunflowers (eg Sclerotinia sclerotium rum) and soybeans (eg BS rolfsii); Septoria spp. on different plants, eg.
  • BS glycines leaf spot on soybeans, S. tritici (Septoria leaf drought) on wheat and S. (Syn. Stagonospora) nodorum (leaf and spelled tan) on cereals; Uncinula (Syn. Erysiphe) necator (powdery mildew, anamorphic: Oidium tuckeri) on grapevine; Sexspaeria spp. (Leaf spot) on corn (for example, S. turcicum, Syn. Helminthosporium turcicum) and turf; Sphacelotheca spp.
  • BT deformans curling disease
  • T. pruni pocket disease
  • Thielaviopsis spp. Black root rot
  • tobacco, pome fruit, vegetable crops, soybeans and cotton eg. BT basicola (Syn: Chalara elegans); Tilletia spp. (Stone or Stinkbrand) of cereals, such.
  • BT tritici Syn. T. caries, Weizensteinbrand
  • T. controversa Zwergsteinbrand
  • Typhula incarnata snow
  • Urocystis spp. E.g.
  • BU occulta (stalk brandy) on rye; Uromyces spp. (Rust) on vegetables, such as beans (for example, appendiculatus appendix, Syn. U. phaseoli) and sugar beet (for example, Betae); Ustilago spp. (Firefighting) on cereals (for example BU nuda and U. avaenae), maize (for example BU maydis: maize buckthorn brandy) and sugarcane; Venturia spp. (Scab) on apples (eg BV inaequalis) and pears; and Verticillium spp. (Deciduous and cloudy wilt) on various plants, such as fruit and ornamental trees, vines, soft fruit, vegetables and crops, such. BV dahliae on strawberries, rapeseed, potatoes and tomatoes.
  • Uromyces spp. (Rust) on vegetables, such as beans (for example, appendiculatus append
  • harmful fungi in particular are considered: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp .; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., moreover, in the protection of the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • plant health includes those conditions of a plant and / or its crop which are determined by various indicators individually or in combination with one another, such as yield (eg, increased biomass and / or increased content of utilizable ingredients), plant vitality (eg increased plant growth and / or greener leaves), quality (eg increased content or composition of certain ingredients) and tolerance to biotic and / or abiotic stress.
  • yield eg, increased biomass and / or increased content of utilizable ingredients
  • plant vitality eg increased plant growth and / or greener leaves
  • quality eg increased content or composition of certain ingredients
  • tolerance to biotic and / or abiotic stress e.g., tolerance to biotic and / or abiotic stress.
  • the compounds I and II can be applied simultaneously, jointly or separately or in succession, the sequence in the case of separate application generally having no effect on the control result.
  • the method for controlling harmful fungi is by the separate or combined application of the compound I and the compound II or the mixtures of the compound I and the compound II by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
  • the active compounds I and II can also be used in the form of their agriculturally acceptable salts. Usually come for alkali or alkaline earth salts, such as sodium, potassium or calcium salts in question, or other salts, as described in this application for compounds of formula I.
  • mixtures of the compounds I and II are used as such or in the form of a composition in which the harmful fungi, their habitat or the plants to be protected against fungal attack, plant propagation materials, eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the compounds I.
  • plant propagation materials eg. As seeds, the soil, surfaces, materials or spaces treated with a fungicidally effective amount of the compounds I.
  • the application may be both before and after the infection of the plants, plant propagation materials, eg. As seeds, the soil, the surfaces, materials or spaces made by the fungi.
  • the invention therefore also encompasses agents or agrochemical compositions which contain a solid or liquid carrier and a fungicidal mixture according to the invention.
  • liquid carrier is used in this context synonymous with solvents.
  • the term "effective amount” means an amount of the agrochemical composition or of the mixture of the compounds I and II which is sufficient for controlling harmful fungi on crop plants or in the protection of materials and buildings and does not lead to considerable damage to the treated crop plants Such an amount may vary within a wide range and is influenced by numerous factors, such as the harmful fungus to be controlled, the particular crop or material being treated, climatic conditions and compounds.
  • compositions of the invention comprising a compound I and another active ingredient, e.g. contain an active ingredient from groups 2.1 to 2.6, the weight ratio of compound I to the further active ingredient is usually in the range of 1: 100 to 100: 1, often in the range of 1:50 to 50: 1, preferably in the range of 1:20 to 20: 1, more preferably in the range of 1:10 to 10: 1, in particular in the range of 1: 3 to 3: 1.
  • the further active components are added to the mixture of compound I and compound II in a ratio of from 20: 1 to 1:20.
  • composition according to the invention can be mixed individually or already mixed or packaged as parts according to the kit of parts and reused.
  • kits one or more, also all, contain components that can be used to prepare an agrochemical composition of the invention.
  • these kits may contain one or more fungicidal component (s) and / or an adjuvant component and / or an insecticidal component and / or a growth regulator component and / or a herbicide.
  • fungicidal component s
  • an adjuvant component / or an insecticidal component and / or a growth regulator component and / or a herbicide.
  • One or more components may be combined or pre-formulated.
  • the components may be combined together and packaged in a single container such as a vessel, bottle, can, bag, sack or canister.
  • two or more components of a kit may be packaged separately, ie, not pre-formulated or mixed.
  • Kits may contain one or more separate containers such as containers, bottles, cans, bags, sacks or canisters, each container containing a separate component of the agrochemical composition.
  • the components of the composition according to the invention can be mixed individually or already mixed or packaged as parts according to the "kit of parts" and reused. In both forms, one component can be used separately or together with the other components or as part of a kit of parts according to the invention for the preparation of the mixture according to the invention.
  • the user usually uses the composition according to the invention for use in a pre-metering device, in the back splash, in the spray tank or in the spray plane.
  • the agrochemical composition with water and / or buffer is brought to the desired application concentration, optionally further adjuvants are added, and thus the ready-spray mixture or the agrochemical composition according to the invention is obtained.
  • 50 to 500 liters of ready-spray mixture per hectare of agricultural land preferably 100 to 400 liters.
  • the user may include individual components such as B. parts of a kit or a two or three-mixture of the composition of the invention itself in the spray tank and optionally add further auxiliaries (tank mix).
  • individual components such as B. parts of a kit or a two or three-mixture of the composition of the invention itself in the spray tank and optionally add further auxiliaries (tank mix).
  • the user can mix both individual components of the composition according to the invention and partially premixed components, for example components containing compounds I and / or active compounds from groups 2.1 to 2.6, in the spray tank and optionally add further auxiliaries (tank mix).
  • the user can use both individual components of the composition according to the invention and partially premixed components, for example components containing compounds I and / or active compounds from groups 2.1 to 2.6, together (for example as a tank mix) or in succession.
  • the application rates of the mixtures according to the invention are between 0.001 and 2.0 kg of active ingredient mixture per ha, preferably between 0.005 and 2 kg per ha, more preferably between 0.05 and 0.9 kg per ha, in particular between 0.1 and 0.75 kg per ha.
  • the application rates for the compound 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 correspondingly generally 1 to 2000 g / ha, preferably 10 to 900 g / ha, in particular 40 to 500 g / ha.
  • the mixtures according to the invention of the compounds I and II and their N-oxides and salts, or the compound I and the compound II and their respective N-oxides and salts can be converted into the types customary for agrochemical compositions, eg. As solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • agrochemical compositions eg. As solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the type of composition depends on the respective intended use; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
  • composition in particular "agrochemical composition”, and “formulation”.
  • composition types are suspensions (SC, OD, FS), pastes, pastilles, wettable powders or dusts (WP, SP, SS, WS, DP, DS) or granules (GR, FG, GG, MG) which are either in Water may be soluble or dispersible, and gels for the treatment of plant propagating materials such as seed (GF).
  • SC suspensions
  • WP wettable powders or dusts
  • WP wettable powders or dusts
  • GR granules
  • FG GG
  • MG granules
  • composition types such as DP, DS, GR, FG, GG and MG are generally used undiluted.
  • the compounds I and II can be present in a common composition or in separate compositions.
  • the type and preparation of the particular composition corresponds to the type and preparation as generally described for compositions herein.
  • the agrochemical compositions are prepared in a known manner (see, for example, US 3,060,084, EP-A 707,445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec.
  • auxiliaries customary for crop protection agents, the choice of auxiliaries being based on the specific application form or the active substance.
  • suitable auxiliaries are solvents, solid carriers, surface-active substances (such as further solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if appropriate dyes and adhesives (for example for seed treatment).
  • Suitable solvents include water, organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.
  • solvent mixtures and mixtures of the abovementioned solvents and water can also be used.
  • Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, 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.
  • surface-active substances adjuvants, wetting agents, adhesives, dispersants or emulsifiers
  • the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids eg.
  • lignin B. of lignin (Borresperse ® grades, Borregaard, Norway), phenol, naphtha lin (Morwet ® types, Akzo Nobel, USA) and dibutyl (nekal ® - types, BASF, Germany), and of fatty acids , Alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of Naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol
  • thickeners ie, compounds that give the composition a modified flow properties, ie high viscosity at rest and low viscosity in motion
  • thickeners are polysaccharides and organic and inorganic sheet minerals, such as xanthan gum (Kelzan ®, CP Kelco, U.S.A.), Rhodopol ® 23 (Rhodia, France) or Veegum ® (RT Vanderbilt, USA) or attaclay ® (Engelhard Corp., NJ, USA).
  • Bactericides may be added to stabilize the composition.
  • bactericides are those based on dichlorophen and benzyl alcohol hemiformal (Proxel ®.. Of Messrs. ICI or Acetide ® RS from Thor Chemie and Kathon ® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acetide ® MBS Fa. Thor Chemie).
  • Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.
  • defoamers examples include silicone emulsions (such as, for example, silicone ® SRE, Wacker, Germany or Rhodorsil ®, Rhodia, France), long chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned are those under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1, Pigment blue 15: 4, Pigment blue 15: 3, Pigment blue 15: 2, Pigment blue 15: 1, Pigment blue 80 , Pigment yellow low 1, Pigment yellow 13, Pigment red 48: 2, Pigment red 48: 1, Pigment red 57: 1, Pigment red 53: 1, Pigment orange 43, Pigment orange 34, Pigment orange 5, Pigment green 36 Pigment green 7, Pigment white 6, Pigment brown 25, Basic violet 10, Basic violet 49, Acid red 51, Acid red 52, Acid red 14, Acid blue 9, Acid yellow 23, Basic red 10, Basic red 108 well-known dyes and pigments.
  • adhesives examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and cellulose ethers (Tylose ®, Shin-Etsu, Japan).
  • 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, metha- nol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
  • 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,
  • Powders, dispersants and dusts can be prepared by mixing or jointly grinding the compounds I and II and, if present, further active compounds with at least one solid carrier.
  • Granules for. As coated, impregnated and homogeneous granules can be prepared by binding the active compounds or drug mixtures to at least one solid carrier.
  • Solid carriers are z.
  • mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, DoIo with, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground
  • Plastics such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • composition types are: 1. Compositions for dilution in water i) Water-soluble concentrates (SL, LS)
  • the active compounds or active substance mixtures are dissolved in 35 parts by weight of xylene with 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 Ultra-Turrax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • the composition has an active ingredient content of 25 wt .-%. v) suspensions (SC, OD, FS)
  • compositions of the mixtures according to the invention generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the compounds I and II.
  • the compounds I and II are in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum) used.
  • For the treatment of plant propagation materials in particular seed, usually water-soluble concentrates (LS), suspensions (FS), dusts (DS), water-dispersible and water-soluble powders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) and gels ( GF).
  • LS water-soluble concentrates
  • FS suspensions
  • dusts DS
  • WS, SS water-dispersible and water-soluble powders
  • ES emulsions
  • EC emulsifiable concentrates
  • gels GF
  • the corresponding composition can be diluted 2 to 10 times, so that 0.01 to 60% by weight, preferably 0.1 to 40% by weight of active compound are present in the compositions to be used for the stain.
  • the application can be done before or during sowing.
  • the treatment of plant propagation material in particular the treatment of seed, are known to the person skilled in the art and are carried out by dusting, coating, pelleting, dipping or impregnating the plant propagation material, wherein the treatment preferably takes place by pelleting, coating and dusting or by furrow treatment, so that z. B. premature germination of the seed is prevented.
  • suspensions are preferably used.
  • such compositions contain 1 to 800 g / l active ingredient, 1 to 200 g / l surfactants, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to 200 g / l dyes and solvents, preferably water ,
  • the active compounds or mixtures of active substances may be used as such or in the form of their compositions, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, dusting, scattering, brushing, dipping or pouring.
  • the composition types or forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds or active substance mixtures according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by adding water.
  • the substances for the preparation of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier.
  • wetter tackifier
  • dispersant or emulsifier it is also possible to prepare from active substance wetting, adhesion, dispersing or emulsifying agents and any solvents 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.
  • Oils of various types, wetting agents, adjuvants, herbicides, bactericides, other fungicides, and / or other pesticides, bactericides, optionally also immediately before use (tank mix), can be added to the active compounds or active ingredient mixtures or to the compositions containing them. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
  • Suitable adjuvants in this sense are in particular: organically modified polysiloxanes, for example 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. Pluronic RPE 2035 ® and Genapol B ®; Alcohol ethoxylates, eg. As Lutensol XP 80 ®; and sodium dioctylsulfosuccinate, e.g. B. Leophen RA ®.
  • organically modified polysiloxanes for example 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. Pluronic RPE 20
  • the invention also encompasses mixtures of component 1 (compounds of the formula I) with one or more further active compounds, eg. As with herbicides, insecticides, growth regulators or with fertilizers, as a pre-mix or possibly only immediately before use (tank mix), these agents can be used alternatively or additionally to the compound II (component 2).
  • component 1 compounds of the formula I
  • further active compounds eg. As with herbicides, insecticides, growth regulators or with fertilizers, as a pre-mix or possibly only immediately before use (tank mix), these agents can be used alternatively or additionally to the compound II (component 2).
  • the spectrum of action can be broadened or resistance developments can be prevented.
  • synergistic effects are obtained. This also applies to the mixture of compound I alone with one or more further active ingredients.
  • compositions for mixtures of active ingredients in a known manner in the form of compositions containing in addition to the active ingredients, a solvent or solid carrier, for. B. in the manner as indicated for compositions of the mixtures of compound I and compound II.
  • a solvent or solid carrier for. B.
  • compositions for mixtures of active compounds are suitable as fungicides for controlling harmful fungi and are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, as described for the mixtures according to the invention of the compounds I and compounds II.
  • Acetamides acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamide, pretilachlor, propachlor, thenylchloro;
  • Amino acid analogues bilanafos, glyphosate, glufosinate, sulfosate;
  • Aryloxyphenoxypropionates Clodinafop, Cyhalofop-butyl, Fenoxaprop, Fluazifop, Haloxyfop, Metamifop, Propaquizafop, Quizalofop, Quizalofop-P-tefuryl;
  • Bipyridyls diquat, paraquat;
  • Carbamates and thiocarbamates asulam, butylates, carbamides, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinates, orbencarb, phenmedipham, prosulphocarb, pyributicarb, thiobencarb, triallates;
  • Diphenyl ether acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
  • Hydroxybenzonitriles bromoxynil, dichlobenil, loxynil;
  • Imidazolinone imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr;
  • Phenoxyacetic acids clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprop;
  • - pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, pilinoram, picolinafen, thiazopyr;
  • Sulfonylureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, lodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosul furon, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-prop
  • Triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozine, hexazinone, metachronon, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
  • Ureas chlorotoluron, da- muron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron; - other inhibitors of acetolactate synthase: bispyribac sodium, cloransulam methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulphamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxime, pyriftalid, pyriminobac-methyl, pyrimisulphane, pyrithiobac, pyroxasulphone, pyroxsulam; - Other: Amicarbazone, Aminotriazole, Anilofos, Beflubutamide, Benazoline, Bencarbazone, Benfluresat, Benzofenap, Bentazone,
  • Carbamates alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamates;
  • - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalo- thrin, permethrin, prallethrin
  • GABA antagonists endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1- (2,6-dichloro-4-methylphenyl) -4-sulfinamoyl-1H-pyrazole-3-thiocarbon acid amide;
  • Macrocyclic lactones abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
  • Inhibitors of the sloughing of insects Cryomazine; Inhibitors of mixed function oxidases: piperonyl butoxide;
  • compositions according to the invention which contain an active substance I and a further active ingredient and a further active ingredient, eg. B. contain two different agents from groups 2.1 to 2.6 or A to C
  • the weight ratio of compound I to the first further active ingredient depends on the properties of the respective active ingredients, preferably in the range of 1:50 to 50: 1 and in particular in the range from 1:10 to 10: 1.
  • the weight ratio of compound I to the second further active ingredient is preferably in the range from 1:50 to 50: 1, in particular in the range from 1:10 to 10: 1.
  • the weight ratio of 1. further active ingredient to the second further active ingredient is preferably in the range from 1:50 to 50: 1, in particular in the range from 1:10 to 10: 1.
  • compositions listed in Table B wherein in each case one row of Table B corresponds to a fungicidal composition comprising a compound of the formula I (component 1), which is preferably one of the compounds described herein as preferred, and in each case in the respective
  • component 1 in each row of table 2 is in each case one of the compounds of the formula I which are specifically individualized in tables 1 to 13, preferably in tables 1 to 7.
  • 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 DMSO and the emulsifier Wettol EM 31 (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. The- The stock solution was diluted with the described solvent-emulsifier-water mixture to the active ingredient concentration given below.
  • Wettol EM 31 wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • the determined values for the percentage infestation on the leaves were converted into efficiencies% of the untreated control.
  • Efficiency 0 means the same infestation as in the untreated control;
  • Efficiency 100 is 0% infestation.
  • the expected efficiencies for drug combinations were determined according to the Colby formula (Colby, S.R. (Calculating Synergistic and Antagonistic Ac- tions of herbicide Combinations, Weeds, 5, p. 20-22, 1967) and compared with the observed efficiencies.
  • 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.
  • the active ingredients were formulated separately or together as stock solution with a concentration of 10,000 ppm in DMSO.
  • the active substances epoxiconazole and trifloxystrobin were used as commercially available formulations and diluted with water in relation to the active ingredient.
  • the measured parameters were compared with the growth of the drug-free control variant (100%) and the fungus- and drug-free blank to determine the relative growth in% of the pathogens in the individual drugs.
  • the determined values for the percentage of relative growth were first averaged, then converted into efficiencies as% of the drug-free control variant. Efficiency 0 is the same growth as in the drug-free control variant, efficiency 100 is 0% growth.
  • the expected efficiencies for drug combinations were determined as above according to the Colby formula and compared with the observed efficiencies.
  • the stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. This was followed by the addition of an aqueous pea-based zoospore suspension of Phytophthora infestans.
  • 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.
  • MTP microtiter plate
  • a malt-based aqueous spore suspension of Botrytis cinerea was added.
  • 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.
  • MTP microtiter plate
  • a malt-based aqueous spore suspension of Pyricularia oryzae was added.
  • 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.
  • the stock solution was pipetted into a microtiter plate (MTP) and diluted with water to the stated drug concentration. This was followed by the addition of an aqueous spore suspension based on malt of Septoria tritici.
  • 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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Abstract

Mélanges fongicides qui contiennent en tant qu'ingrédients actifs (1) des azolylméthyloxiranes de formule générale (I) dans laquelle A représente phényle substitué par trois F, B représente pyridyle, thiényle, thiazolyle, oxazolyle ou furyle non substitués ou phényle substitué par un à trois des substituants suivants : halogène, NO2, amino, alkyle C1-C4, alcoxy C1-C4, halogénoalkyle C1-C4, halogénoalcoxy C1-C4, alkylamino C1-C4, dialkylamino C1-C4, thio ou alkylthio C1-C4, ainsi que leurs sels métalliques et d'addition d'acide phytocompatibles, et (2) un composé fongicide II tel que décrit dans la demande. La présente invention concerne également l'utilisation de ces mélanges fongicides pour lutter contre les champignons phytopathogènes et des produits les contenant.
PCT/EP2008/065964 2007-12-05 2008-11-21 Mélanges fongicides WO2009071450A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010146029A3 (fr) * 2009-06-16 2011-08-11 Basf Se Mélanges fongicides

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0196038A2 (fr) * 1985-03-29 1986-10-01 BASF Aktiengesellschaft Azolylméthyloxiranes, leur préparation et leur utilisation comme agents protecteurs pour les plantes
EP0421125A2 (fr) * 1989-09-09 1991-04-10 BASF Aktiengesellschaft Azolméthyloxirannes fongicides
WO2003084330A1 (fr) * 2002-04-05 2003-10-16 Basf Aktiengesellschaft Melanges fongicides a base de derives de benzamidoxime et d'azoles
WO2007009969A2 (fr) * 2005-07-18 2007-01-25 Basf Aktiengesellschaft Utilisation combinee de metconazole et d'epoxiconazole pour reduire ou empecher la contamination de cereales par des mycotoxines
WO2007028753A2 (fr) * 2005-09-09 2007-03-15 Basf Aktiengesellschaft Melanges fongicides a base de triazoles
WO2007031489A1 (fr) * 2005-09-16 2007-03-22 Basf Se Melanges fongicides a base de triazoles
WO2007045455A1 (fr) * 2005-10-20 2007-04-26 Syngenta Participations Ag Compositions fongicides
WO2007134777A2 (fr) * 2006-05-24 2007-11-29 Bayer Cropscience Ag Combinaisons de principes actifs fongicides
WO2007147769A1 (fr) * 2006-06-23 2007-12-27 Basf Se Azolylméthyloxirane, son utilisation pour lutter contre les champignons pathogènes des plantes et agents contenant ce composé
WO2008003622A1 (fr) * 2006-07-05 2008-01-10 Basf Se Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant
WO2008003607A1 (fr) * 2006-07-05 2008-01-10 Basf Se Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0196038A2 (fr) * 1985-03-29 1986-10-01 BASF Aktiengesellschaft Azolylméthyloxiranes, leur préparation et leur utilisation comme agents protecteurs pour les plantes
EP0421125A2 (fr) * 1989-09-09 1991-04-10 BASF Aktiengesellschaft Azolméthyloxirannes fongicides
WO2003084330A1 (fr) * 2002-04-05 2003-10-16 Basf Aktiengesellschaft Melanges fongicides a base de derives de benzamidoxime et d'azoles
WO2007009969A2 (fr) * 2005-07-18 2007-01-25 Basf Aktiengesellschaft Utilisation combinee de metconazole et d'epoxiconazole pour reduire ou empecher la contamination de cereales par des mycotoxines
WO2007028753A2 (fr) * 2005-09-09 2007-03-15 Basf Aktiengesellschaft Melanges fongicides a base de triazoles
WO2007031489A1 (fr) * 2005-09-16 2007-03-22 Basf Se Melanges fongicides a base de triazoles
WO2007045455A1 (fr) * 2005-10-20 2007-04-26 Syngenta Participations Ag Compositions fongicides
WO2007134777A2 (fr) * 2006-05-24 2007-11-29 Bayer Cropscience Ag Combinaisons de principes actifs fongicides
WO2007147769A1 (fr) * 2006-06-23 2007-12-27 Basf Se Azolylméthyloxirane, son utilisation pour lutter contre les champignons pathogènes des plantes et agents contenant ce composé
WO2008003622A1 (fr) * 2006-07-05 2008-01-10 Basf Se Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant
WO2008003607A1 (fr) * 2006-07-05 2008-01-10 Basf Se Azolylméthyloxyranes, leur utilisation pour lutter contre des champignons phytopathogènes et agents les contenant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010146029A3 (fr) * 2009-06-16 2011-08-11 Basf Se Mélanges fongicides

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TW200932115A (en) 2009-08-01
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PE20091264A1 (es) 2009-09-19

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