WO2011138345A2 - Mélanges fongicides à base d'esters d'acide gallique - Google Patents

Mélanges fongicides à base d'esters d'acide gallique Download PDF

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WO2011138345A2
WO2011138345A2 PCT/EP2011/057081 EP2011057081W WO2011138345A2 WO 2011138345 A2 WO2011138345 A2 WO 2011138345A2 EP 2011057081 W EP2011057081 W EP 2011057081W WO 2011138345 A2 WO2011138345 A2 WO 2011138345A2
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iii
methyl
alkyl
triazolo
pyrimidin
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PCT/EP2011/057081
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WO2011138345A3 (fr
Inventor
Angel Rodriguez-Tello
Gerd Stammler
Alexander Kopf
Randall Evan Gold
Kristin Klappach
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Basf Se
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Publication of WO2011138345A3 publication Critical patent/WO2011138345A3/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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests

Definitions

  • the present invention relates to a fungicidal mixture comprising, as active components: 1 ) gallic acid esters of the formula I
  • Y is Ci-Ci2-alkyl
  • At least one active compound II selected from the following groups
  • R 1 is C3-Ci2-alkyl, C2-Ci2-alkenyl, C5-Ci2-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-Ci-C4-alkyl;
  • R 2 is Ci-Ci2-alkyl, C 2 -Ci 2 -alkenyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl; where the aliphatic chains in R 1 and/or R 2 may be substituted by one to four identical or different groups R a :
  • R a is halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C3-C8-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C 6 -alkoxy-Ci-C 6 -alkyl or NR A R B ;
  • R A , R B are hydrogen and Ci-C6-alkyl
  • R 1 and/or R a may be substituted by one to four groups R b :
  • R b is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-C6-alkoxy;
  • R 3 is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, Ci-C6-alkyl,
  • Ci-C6-haloalkyl Cs-Cs-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C8-cycloalkoxy, Cs-Cs-cycloalkylthio, carboxyl, formyl,
  • Ci-Cio-alkylcarbonyl Ci-Cio-alkoxycarbonyl, C2-Cio-alkenyloxycarbonyl, C2-Cio-alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio, Ci-C 6 -alkyl-S(0) m -;
  • n 0, 1 or 2;
  • carboxanilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fenfuram, fenhexamid, flutolanil, fluxapyroxad, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4-methyl-thiazole-5-carboxanilide, N-(4'-trifluoromethylthiobi- phenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide and N-(2- (1 ,3,3-
  • benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide;
  • carpropamid carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide; in a synergistically effective amount.
  • the present invention relates to an agrochemical composition, comprising a liquid or solid carrier and the fungicidal mixture.
  • the present invention relates to seed, comprising the fungicidal mixture or the composition in an amount of form 1 to 1000 g/100 kg of seed.
  • the present invention relates to a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of the fungicidal mixture or the composition.
  • the present invention relates to a method for improving plant health, comprising treating a plant, its propagation material, the lotus where the plant is growing or is to grow with an effective amount of the fungicidal mixture or the composition.
  • the fungicidal mixtures comprising compound of the formula I and at least one compound II.
  • the mixtures of the compound of the formula I and an active compound II or the simultaneous, that is joint or separate, use of the compounds I and an active compound II are/is distinguished by excellent activity against a broad spectrum of phytopathogenic fungi. Some of them are systemically active and can be used in crop protection as foliar fungicides, as fungicides for seed dressing and as soil fungicides.
  • C x -C y denotes the number of possible carbon atoms in the particular case.
  • halogen fluorine, bromine, chlorine or iodine, especially fluorine, chlorine or bromine; alkyl and the alkyl moieties of composite groups such as, for example, alkoxy, alkylamino, alkoxycarbonyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 12 carbon atoms, for example Ci-Ci2-akyl, such as methyl, ethyl, propyl, 1 - methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluorine, chlorine or bromine.
  • a particular halogen atom preferably fluorine, chlorine or bromine.
  • the alkyl groups are partially or fully halogenated by different halogen atoms; in the case of mixed halogen
  • substitutions the combination of chlorine and fluorine is preferred.
  • Particular preference is given to (Ci-C3)-haloalkyl, more preferably (Ci-C2)-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,
  • alkenyl and also the alkenyl moieties in composite groups such as alkenyloxy:
  • unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one double bond in any position.
  • small alkenyl groups such as (C2-C4)-alkenyl
  • larger alkenyl groups such as (C5-C8)-alkenyl.
  • alkenyl groups are, for example, C2-C6-alkenyl, such as ethenyl, 1 - propenyl, 2-propenyl, 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 - propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1 -pentenyl,
  • alkynyl and the alkynyl moieties in composite groups straight-chain or branched hydrocarbon groups having 2 to 4, 2 to 6 or 2 to 8 carbon atoms and one or two triple bonds in any position, for example C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2- propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl,
  • cycloalkyl and also the cycloalkyl moieties in composite groups mono- or bicyclic saturated hydrocarbon groups having 3 to 8, in particular 3 to 6, carbon ring members, for example C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • bicyclic radicals comprise bicyclo[2.2.1]heptyl, bicyclo[3.1 .1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • optionally substituted Cs-Cs-cycloalkyl means a cycloalkyl radical having from 3 to 8 carbon atoms, in which at least one hydrogen atom, for example 1 , 2, 3, 4 or 5 hydrogen atoms, is/are replaced by substituents which are inert under the conditions of the reaction.
  • substituents which are inert under the conditions of the reaction.
  • inert substituents are CN, Ci-C6-alkyl, Ci-C4-haloalkyl, C1-C6- alkoxy, C3-C6-cycloalkyl, and Ci-C4-alkoxy-Ci-C6-alkyl;
  • alkoxy an alkyl group as defined above which is attached via an oxygen, preferably having 1 to 8, more preferably 2 to 6, carbon atoms.
  • Examples are: methoxy, ethoxy, n- propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy or 1 ,1 - dimethylethoxy, and also for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 - ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4- methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethy
  • phenyl-Ci-C6-alkyl Ci-C6-alkyl in which one of the hydrogen atoms is replaced by an optionally substituted phenyl group. Examples are benzyl, 4-methylbenzyl, phenylethyl etc.;
  • alkylthio alkyl as defined above which is attached via an S atom
  • cycloalkylthio cycloalkyl as defined above which is attached via an S atom;
  • hydroxyl OH group which is attached via an O atom
  • cyano CN group which is attached via an C atom
  • formyl CHO group, which is attached via an C atom;
  • gallic acid esters of the formula I referred to above as component 1 , also known as "gallates", are antioxidant compounds widely used in the food, cosmetics and drug industries (Pucci B, et all. Helv. Chim. Acta 2003, 86(2), 247-265). Antifungal activity of octyl gallate is known from Bioorg. Med. Chem. Lett. 2001 ; 12; 1 1 (3); 7-50.
  • Many of the gallic acid esters used in the practice of the present invention are commercially available compounds or may be readily synthesized by methods that are well known in the art, for example, by refluxing gallic acid and the appropriate alcohol (R-OH) in the presence of acid using standard conditions.
  • the fungicidal mixtures comprise a compound of the formula I, in which Y is:
  • fungicidal mixture comprising a compound I, in which A is propyl.
  • azolopyrimidin-7-ylamines of the formula III referred to above as component 2, their preparation and their action against harmful fungi are known from the literature (EP-A 71 792; EP-A 141 317; WO 03/009687; WO 05/087771 ; WO 05/087772; WO 05/087773; WO 2005/087772; WO 2006/087325; WO 2006/092428).
  • Particularly suitable for the mixtures according to the invention are compounds of the formula III in which R 1 is straight-chain or branched C3-Ci2-alkyl or phenyl which may be substituted by one to three halogen or Ci-C4-alkyl groups.
  • the fungicidal mixtures comprise compounds of the formula III in which group R a is absent.
  • a preferred embodiment relates the fungicidal mixtures comprising a compound of the formula III in which R 1 is straight-chain or branched Cs-C-io-alkyl, in particular ethyl, 3,5,5-trimethylhexyl, n-heptyl, n-octyl, n-nonyl and n-decyl.
  • a further embodiment relates to the fungicidal mixtures comprising a compound of the formula III in which R 1 is phenyl which is unsubstituted or substituted by one to four halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl and Ci-C6-alkoxy groups.
  • Preferred compounds of the formula III are those in which R 1 is a substituted phenyl group which corresponds to a group G
  • L 1 is cyano, halogen, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkoxy;
  • L 2 , L 3 independently of one another are hydrogen or one of the groups mentioned under L 1 and
  • # denotes the bond to the azolopyrimidine skeleton.
  • L 1 is cyano, halogen, hydroxyl, mercapto, nitro, NR A R B , Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy, preferably cyano, halogen, Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy.
  • L 2 is hydrogen or one of the groups mentioned above.
  • L 3 is hydrogen, cyano, halogen, hydroxyl, mercapto, nitro, NR A R B , Ci-C6-alkyl, halomethyl or Ci-C2-alkoxy, preferably hydrogen.
  • R 2 is straight-chain or branched Ci-Ci2-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl or Ci-C4-haloalkyl.
  • R 2 is methyl, ethyl, n-propyl, n-octyl, trifluoromethyl or methoxymethyl, in particular methyl, ethyl, trifluoromethyl or methoxymethyl.
  • R 3 is amino
  • One embodiment of the compounds of the formula III relates to those in which A is N. These compounds correspond to the formula IIIA in which the variables are as defined for formula III:
  • Another embodiment of the compounds of the formula III relates to those in which A is CH. These compounds correspond to the formula NIB in which the variables are as defined for formula III:
  • the carbon chains of R 1 and R 2 together do not have more than 12 carbon atoms.
  • Preferred embodiments of the mixtures according to the invention comprise, as active component 2, a compound selected from the following list:
  • the active compounds II of group B) and C), mentioned above as component 2, their preparation and their action against harmful fungi are generally known (cf. Pesticide manuals, http://www.alanwood.net/pesticides/); they are commercially available.
  • the active compounds II of group D), mentioned above as component 2, and their preparation have been described in the international non-published applications WO 2009/071448, WO 2009/071449, WO 2009/101078 and WO 2009/101079.
  • the fungicidal mixtures comprise as active compound II metrafenone.
  • the fungicidal mixtures comprise as active compound I I a compound of group C) selected from: benalaxyl, benalaxyl-M, boscalid , bixafen , fluopyram, fluxapyroxad, isopyrazam, metalaxyl, penflufen, pentihipyrad, sedaxane.
  • group C selected from: benalaxyl, benalaxyl-M, boscalid , bixafen , fluopyram, fluxapyroxad, isopyrazam, metalaxyl, penflufen, pentihipyrad, sedaxane.
  • the fungicidal mixtures comprise as active compound II boscalid.
  • Preferred embodiments relate to the compositions listed in table A, where in each case one row of table A corresponds to a fungicidal composition comprising the particular compound of the formula I mentioned (Component 1 ) and one active compound of the groups mentioned (Component 2), this active compound preferably being selected from the preferred embodiments defined above.
  • Table A
  • a further embodiment relates to the compositions B-1 to B-165 listed in Table B, where a row of Table B corresponds in each case to a fungicidal composition comprising as component 1 an individualized compound of the formula I and the respective further active substance from groups A) to C) (component 2) stated in the row in question.
  • the compositions described comprise the active substances in
  • Table B Composition comprising one individualized compound of the formula I and one further active substance from groups A) to C)
  • the active compounds mentioned above can also be employed in the form of their agriculturally compatible salts. These are usually the alkali metal or alkaline earth metal salts, such as sodium, potassium or calcium salts.
  • the compounds of the formula I and/or the compounds II of the inventive compositions can be present in different crystal modifications, which may differ in biological activity.
  • - azoxystrobin coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, trifloxystrobin, 2-[2-
  • - carboxanilides benalaxyl, benalaxyl-M, benodanil, bixafen, boscalid, carboxin, fen- furam, fenhexamid, flutolanil, fluxapyroxad, furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil,
  • carpropamid carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
  • C) azoles carpropamid, dicyclomet, mandiproamid, oxytetracyclin, silthiofam and N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide;
  • - triazoles azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothio- conazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole;
  • - 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;
  • - pyrimidines bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepani- pyrim, nitrapyrin, nuarimol, pyrimethanil;
  • dicarboximides fluoroimid, iprodione, procymidone, vinclozolin; - non-aromatic 5-membered heterocycles: famoxadone, fenamidone, flutianil, octhilinone, probenazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro- pyrazole-1 -carbothioic acid S-allyl ester;
  • acibenzolar-S-methyl ametoctradin, amisulbrom, anilazin, blasticidin-S, captafol, captan, chinomethionat, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, fenoxanil, Folpet, oxolinic acid, piperalin, proquinazid, pyroquilon, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4- one, 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole and 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo- [1 ,5-a]
  • guanidine guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate);
  • antibiotics kasugamycin, kasugamycin hydrochloride-hydrate, streptomycin, poly- oxine, validamycin A;
  • nitrophenyl derivates: binapacryl, dicloran, dinobuton, dinocap, nitrothal-isopropyl, tecnazen,
  • organometal compounds fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
  • organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofos-methyl;
  • organochlorine compounds chlorothalonil, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pencycuron, pentachlorphenole and its salts, phthalide, quinto- zene, thiophanate-methyl, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide;
  • Ampelomyces quisqualis e.g. AQ 10 ® from Intrachem Bio GmbH & Co. KG, Germany
  • Aspergillus flavus e.g.
  • AFLAGUARD ® from Syngenta, CH
  • Aureobasidium pullulans e.g. BOTECTOR ® from bio-ferm GmbH, Germany
  • Bacillus pumilus e.g. NRRL Accession No. B- 30087 in SONATA ® and BALLAD ® Plus from AgraQuest Inc., USA
  • Bacillus subtilis e.g. isolate NRRL-Nr. B-21661 in RHAPSODY ® , SERENADE ® MAX and
  • BIOCURE ® in mixture with lysozyme
  • BIOCOAT ® from Micro Flo Company, USA (BASF SE) and Arysta
  • Chitosan e.g. ARMOUR-ZEN from BotriZen Ltd., NZ
  • Clonostachys rosea f. catenulata also named Gliocladium catenulatum (e.g. isolate J1446: PRESTOP ® from Verdera, Finland), Coniothyrium minitans (e.g.
  • CONTANS ® from Prophyta, Germany Cryphonectrl-Aparasitica (e.g. Endothl- Aparasitica from CNICM, France), Cryptococcus albidus (e.g. YIELD PLUS ® from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (e.g. BIOFOX ® from S.I.A.P.A., Italy, FUSACLEAN ® from Natural Plant Protection, France),
  • Cryphonectrl-Aparasitica e.g. Endothl- Aparasitica from CNICM, France
  • Cryptococcus albidus e.g. YIELD PLUS ® from Anchor Bio-Technologies, South Africa
  • Fusarium oxysporum e.g. BIOFOX ® from S.I.A.P.A., Italy, FUSACLEAN ® from Natural Plant Protection, France
  • Metschnikowl-Afructicola e.g. SHEMER ® from Agrogreen, Israel
  • Microdochium dimerum e.g. ANTIBOT ® from Agrauxine, France
  • Phlebiopsis gigantea e.g. ROTSOP ® from Verdera, Finland
  • Pseudozyma flocculosa e.g. SPORODEX ® from Plant Products Co. Ltd., Canada
  • Pythium oligandrum DV74 e.g. POLYVERSUM ® from Remeslo SSRO, Biopreparaty, Czech Rep.
  • Reynoutria sachlinensis e.g. REGALIA ® from Marrone Biolnnovations, USA
  • Talaromyces flavus V1 17b e.g.
  • PLANTSHIELD ® der Firma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT PRO ® from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g. TRICHODEX ® and
  • T. harzianum and T. viride e.g. TRICHOPEL from Agrimm Technologies Ltd, NZ
  • T. harzianum ICC012 and T. viride ICC080 e.g. REMEDIER ® WP from Isagro Ricerca, Italy
  • T. polyspo rum and T. harzianum e.g. BINAB ® from BINAB Bio- Innovation AB, Sweden
  • T. stromaticum e.g. TRICOVAB ® from C.E.P.L.A.C.
  • T. virens GL-21 e.g. SOILGARD ® from Certis LLC, USA
  • T. viride TV1 e.g. T. viride TV1 from Agribiotec srl, Italy
  • Ulocladium oudemansii ⁇ RU3 e.g.
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dike- gulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthi- acet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
  • acetochlor alachlor, butachlor, dimethachlor, dimethenamid
  • flufenacet mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
  • - aryloxyphenoxypropionates clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
  • - (thio)carbamates asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
  • acifluorfen acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
  • - imidazolinones imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr
  • - phenoxy acetic 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, picloram, picolinafen, thiazopyr;
  • - sulfonyl ureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl,
  • - triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone,
  • metamitron metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
  • ureas chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;
  • acetolactate synthase inhibitors bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
  • amicarbazone amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin,
  • organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
  • - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfen- valerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
  • - insect growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etox- azole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat;
  • - GABA antagonist compounds endosulfan, ethiprole, fipronil, vaniliprole,
  • - macrocyclic lactone insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
  • - mitochondrial electron transport inhibitor I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
  • oxidative phosphorylation inhibitors cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
  • - moulting disruptor compounds cryomazine; - mixed function oxidase inhibitors: piperonyl butoxide;
  • a further embodiment relates to the compositions C-1 to C-1035 listed in Table C, where a row of Table C corresponds in each case to a fungicidal composition
  • a fungicidal composition comprising as component 1 an individualized compound of the formula I (l-A, l-B, l-C), as component 2: 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-7) and the respective further active substance (component 3) stated in the row in question.
  • compositions described comprise the active substances in
  • Table C Composition comprising one individualized compound of the formula I (l-A, l-B or l-C), 5-ethyl-6-octyl-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7-ylamine (III-7) and one further active substance.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des mélanges fongicides à base d'ester d'acide gallique.
PCT/EP2011/057081 2010-05-06 2011-05-04 Mélanges fongicides à base d'esters d'acide gallique WO2011138345A2 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2745693A1 (fr) 2012-12-20 2014-06-25 Forschungsanstalt Agroscope Reckenholz-Tänikon ART Procédé et composition permettant de lutter contre les champignons phytopathogènes
CN108271461A (zh) * 2018-01-19 2018-07-13 新疆天业（集团）有限公司 一种莲藕种子的处理方法

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2745693A1 (fr) 2012-12-20 2014-06-25 Forschungsanstalt Agroscope Reckenholz-Tänikon ART Procédé et composition permettant de lutter contre les champignons phytopathogènes
CN108271461A (zh) * 2018-01-19 2018-07-13 新疆天业（集团）有限公司 一种莲藕种子的处理方法

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